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WO2021049889A1 - Compound and organic light-emitting device comprising same - Google Patents

Compound and organic light-emitting device comprising same Download PDF

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Publication number
WO2021049889A1
WO2021049889A1 PCT/KR2020/012249 KR2020012249W WO2021049889A1 WO 2021049889 A1 WO2021049889 A1 WO 2021049889A1 KR 2020012249 W KR2020012249 W KR 2020012249W WO 2021049889 A1 WO2021049889 A1 WO 2021049889A1
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substituted
unsubstituted
group
formula
deuterium
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French (fr)
Korean (ko)
Inventor
김선우
홍완표
금수정
김명곤
김경희
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LG Chem Ltd
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LG Chem Ltd
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Priority to CN202080030525.3A priority Critical patent/CN113727985B/en
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Definitions

  • the present specification relates to a compound including an alkyl group substituted with deuterium and an organic light emitting device including the same.
  • the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy by using an organic material.
  • An organic light emitting device using the organic light emitting phenomenon has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic material layer is often made of a multilayer structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device.For example, it may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like.
  • Patent Document 1 Chinese Patent Publication 108586441
  • a compound including an alkyl group substituted with deuterium and an organic light emitting device including the same are provided.
  • An exemplary embodiment of the present specification provides a compound represented by Formula 1 below.
  • A1 and A2 are the same as or different from each other, and each independently a substituted or unsubstituted aliphatic hydrocarbon ring; A substituted or unsubstituted aromatic hydrocarbon ring; Substituted or unsubstituted aromatic heterocycle; Or a condensed ring of a substituted or unsubstituted aliphatic hydrocarbon ring and an aromatic hydrocarbon ring,
  • X1 and X2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group, or directly linked through -CRaRb-, -NRc-, -O-, -PRd-, -S-, -PORe-, -SO 2 -, -SiRfRg-, or -BRh- Obviously,
  • Ra To Rh are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,
  • R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkyl thioxy group; A substituted or unsubstituted arylthioxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfonyl group; A substituted or unsubstituted arylsulfonyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boro
  • Y is an alkyl group having 1 to 3 carbon atoms substituted with deuterium; Or represented by the following formula (2),
  • B1 and B2 are the same as or different from each other, and each independently a substituted or unsubstituted aliphatic hydrocarbon ring; Or a substituted or unsubstituted aromatic hydrocarbon ring,
  • R6 and R7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkyl thioxy group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,
  • r1 and r2 are the same as or different from each other, and each independently an integer of 1 to 3,
  • r3 and r5 to r7 are the same as or different from each other, and each independently an integer of 1 to 11,
  • r4 is an integer of 1 or 2
  • n is an integer of 1 or 2
  • r4+n is an integer of 2 or 3
  • Y is an alkyl group having 1 to 3 carbon atoms substituted with deuterium
  • at least one of X1, X2 and R1 to R5 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium
  • Y is represented by Formula 2, at least one of X1, X2 and R1 to R7 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium,
  • the compounds described herein can be used as a material for an organic material layer of an organic light-emitting device.
  • the compound according to at least one exemplary embodiment may improve efficiency, low driving voltage, and/or improve lifespan characteristics in an organic light-emitting device.
  • the compounds described herein may be used as a hole injection, hole transport, hole injection and hole transport, electron blocking, light emission, hole blocking, electron transport, or electron injection material.
  • the present Chemical Formula 1 has an effect of improving the conjugation and stability of the compound by including an alkyl group substituted with deuterium.
  • FIG. 1 shows an example of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 7 and a cathode 11 are sequentially stacked.
  • FIG. 2 shows a substrate 1, an anode 2, a first hole injection layer 3, a second hole injection layer 4, a hole transport layer 5, an electron blocking layer 6, a light emitting layer 7, and
  • An example of an organic light-emitting device in which the first electron transport layer 8, the second electron transport layer 9, the electron injection layer 10, and the cathode 11 are sequentially stacked is shown.
  • the present invention provides a compound containing an alkyl group having 1 to 3 carbon atoms substituted with deuterium, and an organic light emitting device including the same. Since the CD bond of the compound of the present invention is stronger than that of the CH bond, the stability of the compound can be improved. When the chemical decomposition of the luminescent compound involves the destruction of the relatively weak C(sp 3 )-H bond, there is an effect of further improving the stability of the compound by using a stronger CD bond than the CH bond.
  • an alkyl group is used as a substituent capable of donating electrons, it is possible to effectively control the luminescence characteristics, but the introduced alkyl group is removed in a high energy state and decomposition of the compound occurs, resulting in a problem in the lifetime characteristics of the overall device.
  • the methyl radical, ethyl radical, and propyl radical which are alkyl radicals having 1 to 3 carbon atoms, are unstable compared to tertiary carbon radicals (more than 4 carbon atoms ), the bond of C(sp 3 )-C(sp 2 ) is destroyed and the resulting compound There is an effect that the decomposition process is relatively suppressed. Therefore, in the case of using an alkyl group having 1 to 3 carbon atoms substituted with deuterium, it is possible to effectively control the light emission characteristics while securing the stability of the blue device.
  • substituted means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, the position where the substituent can be substituted, and when two or more are substituted , Two or more substituents may be the same or different from each other.
  • substituted or unsubstituted refers to deuterium; Halogen group; Nitrile group (-CN); Nitro group; Hydroxy group; Alkyl group; Cycloalkyl group; Alkoxy group; Phosphine oxide group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkylthio group; Arylthio group; Alkylsulfonyl group; Arylsulfonyl group; Alkyl sulfoxy group; Arylsulfoxy group; Alkenyl group; Silyl group; Boron group; Amine group; Aryl group; Or it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, or two or more of the substituents exemplified above are substituted with a connected substituent, or does not have any substituents.
  • a substituent to which two or more substituents are connected may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are connected.
  • substituted or unsubstituted refers to deuterium; Halogen group; Alkyl group; Cycloalkyl group; Alkoxy group; Aryloxy group; Alkylthio group; Arylthio group; Alkylsulfonyl group; Arylsulfonyl group; Silyl group; Boron group; Amine group; Aryl group; Or it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, or two or more of the substituents exemplified above are substituted with a connected substituent, or does not have any substituents.
  • substituted or unsubstituted with A, B or C means that one or more groups selected from the group consisting of substituents A to C or two or more groups selected from the group are substituted or unsubstituted with a linked group.
  • substituted or unsubstituted with -CC may be substituted or unsubstituted with -ABC, may be substituted or unsubstituted with -BCA, may be unsubstituted or substituted with -AAB, or -A-(C ) It may be substituted or unsubstituted with 2 , and is not limited to the above exemplified bar.
  • N% substitution with deuterium means that N% of the hydrogen available in the structure is substituted with deuterium. For example, supposing that 25% of dibenzofuran is substituted with deuterium, it means that two of the eight hydrogens in dibenzofuran have been substituted with deuterium.
  • the degree of deuteration can be confirmed by a known method such as nuclear magnetic resonance spectroscopy (1H NMR) or GC/MS.
  • examples of the halogen group include fluorine (-F), chlorine (-Cl), bromine (-Br), or iodine (-I).
  • the silyl group may be represented by the formula of -SiY a Y b Y c , wherein Y a , Y b and Y c are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group.
  • the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like, but is not limited thereto. Does not.
  • the boron group may be represented by the formula of -BY d Y e , wherein Y d and Y e are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group.
  • the boron group specifically includes a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, and a phenyl boron group, but is not limited thereto.
  • the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to an exemplary embodiment, the alkyl group has 1 to 30 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms.
  • alkyl group examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, pentyl group, n-pentyl group, hexyl group, n -Hexyl group, heptyl group, n-heptyl group, octyl group, n-octyl group, and the like, but are not limited thereto.
  • the alkoxy group may be a straight chain, branched chain, or cyclic chain.
  • the number of carbon atoms of the alkoxy group is not particularly limited, it is preferably 1 to 20 carbon atoms.
  • Substituents including an alkyl group, an alkoxy group and other alkyl group moieties described in the present specification include all of the straight chain or branched form.
  • the cycloalkyl group is not particularly limited, but is preferably 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, and the like, but is not limited thereto.
  • the amine group is -NH 2 , and the above-described alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, and combinations thereof may be substituted in the amine group.
  • the number of carbon atoms of the substituted amine group is not particularly limited, but is preferably 1 to 30. According to an exemplary embodiment, the amine group has 1 to 20 carbon atoms. According to an exemplary embodiment, the amine group has 1 to 10 carbon atoms.
  • substituted amine group examples include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, 9,9-dimethylfluorenylphenylamine group, pyridylphenylamine group, diphenylamine Group, phenylpyridylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, dibenzofuranylphenylamine group, 9-methylanthracenylamine group, diphenylamine group, phenylnaphthylamine group, Although there are a ditolylamine group, a phenyltolylamine group, a diphenylamine group, etc., it is not limited to these.
  • the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms.
  • the aryl group may be a monocyclic aryl group such as a phenyl group, a biphenyl group, a terphenyl group, or a quarterphenyl group, but is not limited thereto.
  • the polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a triphenyl group, a chrysenyl group, a fluorenyl group, a triphenylenyl group, and the like, but is limited thereto. no.
  • the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
  • Spirofluorenyl groups such as, (9,9-dimethylfluorenyl group), and It may be a substituted fluorenyl group such as (9,9-diphenylfluorenyl group). However, it is not limited thereto.
  • aryl group in the aryloxy group may be described above with respect to the aryl group.
  • alkyl group in the alkylthio group and the alkylsulfonyl group.
  • the description of the aryl group described above may be applied to the aryl group in the arylthio group and the arylsulfonyl group.
  • the above-described description of the alkyl group may be applied to the alkyl group in the alkyl thioxy group and the alkyl sulfoxy group.
  • the description of the aryl group described above may be applied to the aryl group in the arylthioxy group and the arylsulfoxy group.
  • the heterocyclic group is a cyclic group including at least one of N, O, P, S, Si, and Se as hetero atoms, and the number of carbons is not particularly limited, but is preferably 2 to 60 carbon atoms. According to an exemplary embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30.
  • heterocyclic group examples include pyridine group, pyrrole group, pyrimidine group, quinoline group, pyridazinyl group, furan group, thiophene group, imidazole group, pyrazole group, dibenzofuran group, dibenzothiophene group , Carbazole group, benzocarbazole group, naphthobenzofuran group, benzonaphthothiophene group, indenocarbazole group, triazinyl group, and the like, but are not limited thereto.
  • heterocyclic group may be applied except that the heteroaryl group is aromatic.
  • ring in a substituted or unsubstituted ring formed by bonding with adjacent groups to each other, "ring" is a hydrocarbon ring; Or a hetero ring.
  • the hydrocarbon ring may be an aromatic, aliphatic, or condensed ring of aromatic and aliphatic, and may be selected from examples of the cycloalkyl group or an aryl group, except that it is a monovalent group.
  • the meaning of forming a ring by bonding with adjacent groups to each other means a substituted or unsubstituted aliphatic hydrocarbon ring by bonding with adjacent groups;
  • the hydrocarbon ring means a ring consisting only of carbon and hydrogen atoms.
  • the heterocycle refers to a ring including at least one selected from N, O, P, S, Si and Se.
  • the aliphatic hydrocarbon ring, the aromatic hydrocarbon ring, the aliphatic hetero ring and the aromatic hetero ring may be monocyclic or polycyclic.
  • the aliphatic hydrocarbon ring refers to a ring that is not aromatic and includes only carbon and hydrogen atoms.
  • Examples of aliphatic hydrocarbon rings include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, and the like, It is not limited to this.
  • the aromatic hydrocarbon ring means an aromatic ring consisting only of carbon and hydrogen atoms.
  • aromatic hydrocarbon rings include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenalene, pyrene, tetracene, chrysene, pentacene, fluorene, indene, acenaphthylene, Benzofluorene, spirofluorene, and the like, but are not limited thereto.
  • the aromatic hydrocarbon ring may be interpreted as having the same meaning as an aryl group.
  • the aliphatic heterocycle means an aliphatic ring containing one or more of heteroatoms.
  • aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxephan, and azocaine , Thiocane, and the like, but are not limited thereto.
  • the aromatic heterocycle means an aromatic ring containing at least one heteroatom.
  • aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, parasol, oxazole, isoxazole, thiazole, isothiazole, triazole, oxadiazole, thia Diazole, dithiazole, tetrazole, pyran, thiopyran, diazine, oxazine, thiazine, dioxin, triazine, tetrazine, isoquinoline, quinoline, quinone, quinazoline, quinoxaline, naphthyridine, acridine , Phenanthridine, diazanaphthalene, dryazainden, indole, indolizine, benzothiazole, benzoxazole, benzoimidazole, benzothi
  • the present specification provides a compound represented by the following formula (1).
  • the compound represented by the following formula (1) is used in the organic material layer of the organic light-emitting device, the efficiency of the organic light-emitting device is improved, as well as a low driving voltage and excellent lifespan characteristics.
  • A1 and A2 are the same as or different from each other, and each independently a substituted or unsubstituted aliphatic hydrocarbon ring; A substituted or unsubstituted aromatic hydrocarbon ring; Substituted or unsubstituted aromatic heterocycle; Or a condensed ring of a substituted or unsubstituted aliphatic hydrocarbon ring and an aromatic hydrocarbon ring,
  • X1 and X2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group, or directly linked through -CRaRb-, -NRc-, -O-, -PRd-, -S-, -PORe-, -SO 2 -, -SiRfRg-, or -BRh- Obviously,
  • Ra To Rh are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,
  • R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkyl thioxy group; A substituted or unsubstituted arylthioxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfonyl group; A substituted or unsubstituted arylsulfonyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boro
  • Y is an alkyl group having 1 to 3 carbon atoms substituted with deuterium; Or represented by the following formula (2),
  • B1 and B2 are the same as or different from each other, and each independently a substituted or unsubstituted aliphatic hydrocarbon ring; Or a substituted or unsubstituted aromatic hydrocarbon ring,
  • R6 and R7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkyl thioxy group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,
  • r1 and r2 are the same as or different from each other, and each independently an integer of 1 to 3,
  • r3 and r5 to r7 are the same as or different from each other, and each independently an integer of 1 to 11,
  • r4 is an integer of 1 or 2
  • n is an integer of 1 or 2
  • r4+n is an integer of 2 or 3
  • Y is an alkyl group having 1 to 3 carbon atoms substituted with deuterium
  • at least one of X1, X2 and R1 to R5 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium
  • Y is represented by Formula 2, at least one of X1, X2 and R1 to R7 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium,
  • the half width of the compound represented by Formula 1 is 17 nm to 35 nm.
  • the alkyl group having 1 to 3 carbon atoms substituted with deuterium is -CDH 2 ; -CD 2 H; -CD 3 ; -C 2 D 5 ; -CH 2 CD 3 ; -CD(CD 3 ) 2 ; Alternatively, it may be represented by -CH(CD 3 ) 2.
  • a methyl group substituted with deuterium may be represented by -CD 3.
  • the ethyl group substituted with deuterium may be represented by -C 2 D 5 (-CD 2 CD 3 ) or CH 2 CD 3.
  • the propyl group substituted with deuterium (-CD(CD 3 ) 2 ) or It can be expressed as (CH(CD 3 ) 2 ). Means the bonding position.
  • A1 and A2 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic to tetracyclic aliphatic hydrocarbon ring; Substituted or unsubstituted mono- to 4-cyclic aromatic hydrocarbon rings; A substituted or unsubstituted monocyclic to 4 ring aromatic heterocycle; Or a substituted or unsubstituted monocyclic to 4 ring aliphatic hydrocarbon ring and a monocyclic to 4 ring condensed ring of aromatic hydrocarbon ring.
  • A1 and A2 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic aliphatic hydrocarbon ring; Substituted or unsubstituted mono- to 4-cyclic aromatic hydrocarbon rings; A substituted or unsubstituted monocyclic to tricyclic aromatic heterocycle; Or a substituted or unsubstituted monocyclic or bicyclic aliphatic hydrocarbon ring and a condensed ring of a monocyclic or bicyclic aromatic hydrocarbon ring.
  • A1 and A2 are the same as or different from each other, and each independently a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms; A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms; A substituted or unsubstituted C2 to C30 aromatic heterocycle; Or a condensed ring of a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms and an aromatic hydrocarbon ring having 6 to 30 carbon atoms.
  • A1 and A2 are the same as or different from each other, and each independently a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 carbon atoms; A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 20 carbon atoms; A substituted or unsubstituted C2 to C20 aromatic heterocycle; Or a condensed ring of a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 carbon atoms and an aromatic hydrocarbon ring having 6 to 20 carbon atoms.
  • A1 and A2 are the same as or different from each other, and each independently a benzene ring unsubstituted or substituted with a phenyl group or a naphthyl group; A substituted or unsubstituted fluorene ring; A substituted or unsubstituted triphenylene ring; A substituted or unsubstituted cyclohexane ring; A substituted or unsubstituted benzene ring condensed with a substituted or unsubstituted cyclopentene or a substituted or unsubstituted cyclohexene; Or a substituted or unsubstituted dibenzofuran ring.
  • A1 and A2 are the same as or different from each other, and each independently is represented by any one of the following Chemical Formulas A100 to A103.
  • G1 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combined with an adjacent group to form a substituted or unsubstituted ring,
  • X11 is O; S; Or CR101R102,
  • R101 and R102 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
  • g1 is an integer from 0 to 5
  • g1' is an integer from 0 to 11
  • g1'' is an integer from 0 to 7
  • g1''' is an integer from 0 to 11
  • a1 is an integer of 1 to 2
  • g1', g1'' and g1''' are each 2 or more, 2 or more G1s are the same as or different from each other,
  • G1 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group, or combine with an adjacent group to form a substituted or unsubstituted ring.
  • G1 is hydrogen; heavy hydrogen; Or an alkyl group having 1 to 30 carbon atoms substituted or unsubstituted with deuterium, or combined with an adjacent group to form an aromatic hydrocarbon ring having 6 to 30 carbon atoms, or directly bonded to R1 or R2 to form a carbazole ring; Hexahydrocarbazole ring; or Form a loop.
  • G1 is hydrogen; heavy hydrogen; Or an alkyl group having 1 to 20 carbon atoms substituted or unsubstituted with deuterium, or combined with an adjacent group to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms, or directly bonded to R1 or R2 to form a carbazole ring; Hexahydrocarbazole ring; or Form a loop.
  • G1 is hydrogen; heavy hydrogen; Or an alkyl group having 1 to 10 carbon atoms substituted or unsubstituted with deuterium, or a benzene ring combined with an adjacent group; Or a phenanthrene ring or a carbazole ring by direct bonding with R1 or R2; Hexahydrocarbazole ring; or Form a loop.
  • G1 is hydrogen; heavy hydrogen; Or an alkyl group having 1 to 4 carbon atoms substituted or unsubstituted with deuterium, or a benzene ring by bonding with an adjacent group; Or a phenanthrene ring or a carbazole ring by direct bonding with R1 or R2; Hexahydrocarbazole ring; or Form a loop.
  • G1 is hydrogen; heavy hydrogen; Or a methyl group unsubstituted or substituted with deuterium; An ethyl group unsubstituted or substituted with deuterium; A propyl group unsubstituted or substituted with deuterium; Or a butyl group substituted or unsubstituted with deuterium, or a phenanthrene ring by bonding with an adjacent group to form a phenanthrene ring, or a carbazole ring by directly bonding with R1 or R2; Hexahydrocarbazole ring; or Form a loop.
  • G1 is hydrogen; heavy hydrogen; Or a methyl group unsubstituted or substituted with deuterium; An ethyl group unsubstituted or substituted with deuterium; I-propyl group unsubstituted or substituted with deuterium; Or a t-butyl group substituted or unsubstituted with deuterium, or bonded to an adjacent group to form a phenanthrene ring, or directly bonded to R1 or R2 to form a carbazole ring; Hexahydrocarbazole ring; or Form a loop.
  • X11 is O; Or CR101R102.
  • R101 and R102 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
  • R101 and R102 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • R101 and R102 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
  • R101 and R102 are the same as or different from each other, and each independently an alkyl group unsubstituted or substituted with deuterium; Or an aryl group unsubstituted or substituted with deuterium.
  • R101 and R102 are the same as or different from each other, and each independently a methyl group unsubstituted or substituted with deuterium; Or a phenyl group.
  • R101 and R102 are methyl groups unsubstituted or substituted with deuterium.
  • R101 and R102 is a methyl group; Or CD 3 .
  • a1 is 1 or 2.
  • g1 is 1 to 4.
  • g1' is 1 to 4.
  • g1'' is 1 to 4.
  • g1"' is 1 to 4.
  • A1 and A2 are the same as or different from each other, and are each independently represented by any one of the following structures.
  • R101 to R103, G101 and G102 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
  • R103 is a substituted or unsubstituted aryl group.
  • R103 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • R103 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
  • R103 is an aryl group unsubstituted or substituted with deuterium, a methyl group, or CD 3.
  • R103 is a phenyl group unsubstituted or substituted with deuterium, a methyl group, or CD 3.
  • R103 is a phenyl group unsubstituted or substituted with CD 3.
  • G101 and G102 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group.
  • G101 and G102 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.
  • G101 and G102 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.
  • G101 and G102 are the same as or different from each other, and each independently a deuterium-substituted or unsubstituted alkyl group.
  • G101 and G102 are methyl groups; Or CD 3 .
  • A1 and A2 are the same as or different from each other, and each independently a benzene ring; Triphenylene ring; Fluorene ring; Cyclohexane ring; Dibenzofuran ring; Benzene ring condensed with cyclopentene; Or a benzene ring condensed with cyclohexane, and the substituents are unsubstituted or substituted with G1.
  • A1 and A2 are the same as or different from each other, and are each independently represented by any one of the following structures.
  • the groups are deuterium; Or it is unsubstituted or substituted with an alkyl group having 1 to 3 carbon atoms.
  • X1 and X2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group, or directly linked through -CRaRb-, -NRc-, -O-, -PRd-, -S-, -PORe-, -SO 2 -, -SiRfRg-, or -BRh- do.
  • X1 and X2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted C1-C20 alkyl group, -CRaRb-, -NRc-, -O-, -PRd-, -S-, -PORe-, -SO 2 -, -SiRfRg-, or -BRh It is connected directly through -.
  • X1 and X2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, -CRaRb-, -NRc-, -O-, -PRd-, -S-, -PORe-, -SO 2 -, -SiRfRg-, or -BRh It is connected directly through -.
  • X1 and X2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or an alkyl group unsubstituted or substituted with deuterium, or through -CRaRb-, -NRc-, -O-, -PRd-, -S-, -PORe-, -SO 2 -, -SiRfRg-, or -BRh- It is directly connected.
  • X1 and X2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or an alkyl group having 1 to 3 carbon atoms substituted or unsubstituted with deuterium.
  • X1 and X2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium; An ethyl group unsubstituted or substituted with deuterium; Or a propyl group unsubstituted or substituted with deuterium.
  • X1 and X2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium; An ethyl group unsubstituted or substituted with deuterium; Or an i-propyl group unsubstituted or substituted with deuterium.
  • X1 and X2 are -CRaRb-, -NRc-, -O-, -PRd-, -S-, -PORe-, -SO 2 -, -SiRfRg-, or -BRh- It is directly connected through.
  • X1 and X2 are directly connected through -CRaRb-, -NRc-, -O-, -S-, -PORe-, -SO 2 -, -SiRfRg-, or -BRh- do.
  • Ra To Rh are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring.
  • Ra To Rh are the same as or different from each other, and each independently an alkyl group unsubstituted or substituted with deuterium; An alkenyl group unsubstituted or substituted with deuterium; An alkynyl group unsubstituted or substituted with deuterium; Arylalkyl group unsubstituted or substituted with deuterium; Aryl group unsubstituted or substituted with deuterium; Or a heterocyclic group substituted or unsubstituted with deuterium, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring with a methyl group substituted with deuterium or deuterium.
  • Ra To Rh are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms; A substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or adjacent groups are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 10 to 30 carbon atoms or a substituted or unsubstituted heterocyclic ring having 12 to 30 carbon atoms do.
  • Ra To Rh are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms; A substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms, or adjacent groups are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 10 to 20 carbon atoms or a substituted or unsubstituted heterocycle having 12 to 20 carbon atoms do.
  • Ra To Rh are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms; A substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted aryl group having 6 to 10 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 10 carbon atoms, or adjacent groups are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 10 to 20 carbon atoms or a substituted or unsubstituted heterocycle having 12 to 20 carbon atoms do.
  • Ra To Rh are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heterocycle.
  • Ra To Rh are the same as or different from each other, and each independently an alkyl group unsubstituted or substituted with deuterium; Aryl group unsubstituted or substituted with deuterium; Or a heterocyclic group substituted or unsubstituted with deuterium, or adjacent groups are bonded to each other to form an aromatic hydrocarbon ring substituted or unsubstituted with deuterium or a substituted or unsubstituted heterocycle.
  • Ra To Rh are the same as or different from each other, and each independently an alkyl group unsubstituted or substituted with deuterium or CD 3; Aryl group unsubstituted or substituted with deuterium or CD 3; Or deuterium, or substituted with a CD 3 or unsubstituted heterocyclic group, or form a substituted or unsubstituted heterocyclic group with the adjacent deuterium or CD 3 groups are bonded to each other to a substituted or unsubstituted aromatic hydrocarbon ring or a deuterium or CD 3 ring do.
  • Ra To Rh are the same as or different from each other, and each independently a substituted or unsubstituted methyl group; Or a substituted or unsubstituted phenyl group, or adjacent groups are bonded to each other to form a substituted or unsubstituted fluorene ring; Or it forms the following structure which is substituted or unsubstituted.
  • Ra To Rh are the same as or different from each other, and each independently a methyl group unsubstituted or substituted with deuterium; Or a phenyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a methyl group, and a hexahydrocarbazole group, or a group to which two or more are connected, or adjacent groups are bonded to each other to form a fluorene ring; Or to form the following structure.
  • the following structure is unsubstituted or substituted with a phenyl group unsubstituted or substituted with CD 3, Means a position to form a ring.
  • Ra To Rh are the same as or different from each other, and each independently CD 3 ; Methyl group; Or a phenyl group unsubstituted or substituted with a hexahydrocarbazole group substituted with CD 3 or CD 3 , or adjacent groups bonded to each other to form a fluorene ring; Or to form the following structure.
  • the following structure is unsubstituted or substituted with a phenyl group unsubstituted or substituted with CD 3, Means a position to form a ring.
  • R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfonyl group; A substituted or unsubstituted arylsulfonyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substitute
  • R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C30 alkyl group; A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms; A substituted or unsubstituted C1 to C30 alkylthio group; A substituted or unsubstituted arylthio group having 6 to 30 carbon atoms; A substituted or unsubstituted C 1 to C 30 alkylsulfonyl group; A substituted or unsubstituted arylsulfonyl group having 6 to 30 carbon atoms; A substituted or unsubstituted amine group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted
  • R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; A substituted or unsubstituted aryloxy group having 6 to 20 carbon atoms; A substituted or unsubstituted C1 to C20 alkylthio group; A substituted or unsubstituted arylthio group having 6 to 20 carbon atoms; A substituted or unsubstituted C 1 to C 20 alkylsulfonyl group; A substituted or unsubstituted arylsulfonyl group having 6 to 20 carbon atoms; A substituted or unsubstituted amine group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted
  • R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms; A substituted or unsubstituted aryloxy group having 6 to 14 carbon atoms; A substituted or unsubstituted C1 to C10 alkylthio group; A substituted or unsubstituted arylthio group having 6 to 14 carbon atoms; A substituted or unsubstituted C 1 to C 10 alkylsulfonyl group; A substituted or unsubstituted arylsulfonyl group having 6 to 14 carbon atoms; A substituted or unsubstituted amine group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted
  • R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; An alkyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a halogen group, an alkyl group, an aryl group, and a heterocyclic group, or a group to which two or more are connected; An alkoxy group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a halogen group, an alkyl group, an aryl group, and a heterocyclic group, or a group to which two or more are connected; An aryloxy group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a halogen group, an alkyl group, an aryl group, and a heterocyclic group, or a group to which two or more are connected; An alkylthio group unsubstituted
  • R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted pentyl group; A substituted or unsubstituted methoxy group; A substituted or unsubstituted methylthio group; A substituted or unsubstituted phenylthio group; A substituted or unsubstituted methylsulfonyl group; A substituted or unsubstituted t-butylsulfonyl group; A substituted or unsubstituted phenylsulfonyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted trimethylsilyl
  • the groups are substituted or unsubstituted with one or more groups selected from the group consisting of deuterium, a halogen group, an alkyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 20 carbon atoms, or a group to which two or more groups are bonded.
  • R1 and R2 are substituted with one or more groups selected from the group consisting of deuterium, -F, methyl group, CD 3 , i-propyl group, t-butyl group, and phenyl group, or a group to which two or more groups are bonded. Or unsubstituted.
  • R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium or -F; An ethyl group unsubstituted or substituted with deuterium or -F; A propyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, -F and a phenyl group, or a group to which two or more are connected; A butyl group unsubstituted or substituted with deuterium or -F; A pentyl group unsubstituted or substituted with deuterium or -F; A methoxy group unsubstituted or substituted with deuterium or -F; A methylthio group unsubstituted or substituted with deuterium or -F; A phenylthio group unsubstituted or substituted with deuterium, a methyl
  • R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium or -F; An ethyl group unsubstituted or substituted with deuterium; An i-propyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium and a phenyl group or a group to which two or more are connected; t-butyl group; t-pentyl group; A methoxy group unsubstituted or substituted with deuterium or -F; A methylthio group unsubstituted or substituted with deuterium or -F; Phenylthio group; A methylsulfonyl group unsubstituted or substituted with deuterium; T-butylsulfonyl group unsubstituted or substituted with deuterium; Phenyl
  • R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium or -F; An ethyl group unsubstituted or substituted with deuterium; An i-propyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium and a phenyl group or a group to which two or more are connected; t-butyl group; t-pentyl group; A methoxy group unsubstituted or substituted with deuterium or -F; Deuterium, -F, a phenyl group unsubstituted or substituted with a methyl group or CD 3 or an amine group substituted with a CD 3; Trimethylsilyl group unsubstituted or substituted with deuterium; Or a phenyl group unsubstituted or substituted with deuteruter
  • R3 and R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted phenylpropyl group; A substituted or unsubstituted adamantyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted pyridyl group; A substituted or unsubstituted carbazole group, or a direct bond with R1 or R
  • the groups are substituted or unsubstituted with one or more groups selected from the group consisting of deuterium, a halogen group, an alkyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 20 carbon atoms, or a group to which two or more groups are bonded.
  • R3 and R5 are substituted with one or more groups selected from the group consisting of deuterium, -F, methyl group, CD 3 , i-propyl group, t-butyl group, and phenyl group, or a group to which two or more groups are bonded. Or unsubstituted.
  • R3 and R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, -F, a methyl group and a phenyl group, or a group to which two or more are connected; An ethyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, -F, a methyl group and a phenyl group, or a group to which two or more are connected; A propyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, -F, a methyl group and a phenyl group, or a group to which two or more are connected; A butyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, -F, a methyl group and
  • R3 and R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium or -F; An ethyl group unsubstituted or substituted with deuterium; An i-propyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium and a phenyl group or a group to which two or more are connected; T-butyl group unsubstituted or substituted with deuterium; Trimethylsilyl group; Diphenylboron group; A phenylpropyl group unsubstituted or substituted with deuterium; Adamantyl group; Deuterium, -F, a methyl group unsubstituted or substituted with deuterium, or a phenyl group unsubstituted or substituted with an i-propyl group substituted or unsubstituted
  • R3 and R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium; An ethyl group unsubstituted or substituted with deuterium; An i-propyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium and a phenyl group or a group to which two or more are connected; T-butyl group unsubstituted or substituted with deuterium; A phenylpropyl group unsubstituted or substituted with deuterium; Or deuterium, a methyl group unsubstituted or substituted with deuterium, or a phenyl group unsubstituted or substituted with an i-propyl group substituted or unsubstituted with deuterium, or a direct bond with R1 or R2; Or an indene ring unsubstit
  • adjacent R1 and R3 combine with each other to form a substituted or unsubstituted ring.
  • adjacent R1 and R3 are bonded to each other to form a substituted or unsubstituted carbazole ring; Substituted or unsubstituted hexahydrocarbazole ring; Or substituted or unsubstituted by being linked through B Form a ring
  • adjacent R1 and R3 are combined with each other to deuterium; Or a carbazole ring unsubstituted or substituted with an alkyl group having 1 to 3 carbon atoms substituted with deuterium; heavy hydrogen; Or a hexahydrocarbazole ring unsubstituted or substituted with an alkyl group having 1 to 3 carbon atoms substituted with deuterium; Or substituted or unsubstituted with a phenyl group linked through B and substituted with CD 3 Form a ring
  • adjacent R1 and R3 combine with each other to form a hexahydrocarbazole ring substituted or unsubstituted with CD 3.
  • adjacent R2 and R5 combine with each other to form a substituted or unsubstituted ring.
  • adjacent R2 and R5 are bonded to each other to form a substituted or unsubstituted carbazole ring; Substituted or unsubstituted hexahydrocarbazole ring; Or substituted or unsubstituted by being linked through B Form a ring
  • adjacent R2 and R5 are combined with each other to deuterium; Or a carbazole ring unsubstituted or substituted with an alkyl group having 1 to 3 carbon atoms substituted with deuterium; heavy hydrogen; Or a hexahydrocarbazole ring unsubstituted or substituted with an alkyl group having 1 to 3 carbon atoms substituted with deuterium; Or substituted or unsubstituted with a phenyl group linked through B and substituted with CD 3 Form a ring
  • adjacent R2 and R5 combine with each other to form a hexahydrocarbazole ring substituted or unsubstituted with CD 3.
  • R1 to R5 are represented by -L-R11,
  • L is a direct bond; O; S; SO 2 ; A substituted or unsubstituted alkylene group; Or a substituted or unsubstituted arylene group,
  • R11 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
  • L is a direct bond; O; S; SO 2 ; A substituted or unsubstituted C 1 to C 20 alkylene group; Or a substituted or unsubstituted C6 to C20 arylene group.
  • L is a direct bond; O; S; SO 2 ; A substituted or unsubstituted C1-C10 alkylene group; Or a substituted or unsubstituted C6 to C10 arylene group.
  • L is a direct bond; O; S; SO 2 ; Or a substituted or unsubstituted C 1 to C 5 alkylene group.
  • L is a direct bond; O; S; SO 2 ; A substituted or unsubstituted methylene group; Or a substituted or unsubstituted methylene group is a propylene group.
  • L is a direct bond; O; S; SO 2 ; A methylene group unsubstituted or substituted with CD 3; Or a propylene group unsubstituted or substituted with deuterium.
  • L is a direct bond; O; A methylene group unsubstituted or substituted with CD 3; Or a propylene group unsubstituted or substituted with deuterium.
  • R11 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
  • R11 is hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted C1 to C20 haloalkyl group; A substituted or unsubstituted amine group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted C2 to C20 heterocyclic group.
  • R11 is hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted haloalkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted amine group having 1 to 15 carbon atoms; A substituted or unsubstituted aryl group having 6 to 10 carbon atoms; Or a substituted or unsubstituted C2 to C10 heterocyclic group.
  • R11 is hydrogen; heavy hydrogen; CD 3 ; CF 3 ; Or a phenyl group unsubstituted or substituted with deuterium or CD 3.
  • R11 is hydrogen; heavy hydrogen; CD 3 ; Or a phenyl group unsubstituted or substituted with deuterium or CD 3.
  • R1 or R2 is a substituted or unsubstituted aliphatic hydrocarbon ring bonded to each other with adjacent groups; A substituted or unsubstituted aromatic hydrocarbon ring; Substituted or unsubstituted aromatic heterocycle; Or it forms a condensed ring of a substituted or unsubstituted aliphatic hydrocarbon ring and an aromatic hydrocarbon ring.
  • R1 or R2 is a substituted or unsubstituted monocyclic to tetracyclic aliphatic hydrocarbon ring by bonding with an adjacent group to each other; Substituted or unsubstituted mono- to 4-cyclic aromatic hydrocarbon rings; A substituted or unsubstituted monocyclic to 4 ring aromatic heterocycle; Or a substituted or unsubstituted monocyclic to 4 ring aliphatic hydrocarbon ring and a monocyclic to 4 ring aromatic hydrocarbon ring to form a condensed ring.
  • R1 or R2 is a substituted or unsubstituted monocyclic aliphatic hydrocarbon ring by bonding to each other with adjacent groups; Substituted or unsubstituted mono- to 4-cyclic aromatic hydrocarbon rings; A substituted or unsubstituted monocyclic to tricyclic aromatic heterocycle; Or a condensed ring of a substituted or unsubstituted monocyclic or bicyclic aliphatic hydrocarbon ring and a monocyclic or bicyclic aromatic hydrocarbon ring.
  • R1 or R2 is a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms by bonding with an adjacent group; A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms; A substituted or unsubstituted C2 to C30 aromatic heterocycle; Alternatively, a condensed ring of a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms and an aromatic hydrocarbon ring having 6 to 30 carbon atoms is formed.
  • R1 or R2 is a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 carbon atoms by bonding with an adjacent group; A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 20 carbon atoms; A substituted or unsubstituted C2 to C20 aromatic heterocycle; Alternatively, a condensed ring of a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 carbon atoms and an aromatic hydrocarbon ring having 6 to 20 carbon atoms is formed.
  • R1 or R2 is each directly bonded to R3 or R5, bonded through B substituted with a substituted or unsubstituted phenyl group, or bonded to an adjacent group through a substituted or unsubstituted phenanthrene.
  • the groups are substituted or unsubstituted with one or more groups selected from the group consisting of deuterium, a halogen group, an alkyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 20 carbon atoms, or a group to which two or more groups are bonded.
  • R1 or R2 is directly bonded to R3 or R5, respectively, or by bonding with an adjacent group to each other to form a substituted or unsubstituted indene ring; A substituted or unsubstituted benzofuran ring; Substituted or unsubstituted benzothiophene ring; A substituted or unsubstituted cyclopentene ring; A substituted or unsubstituted cyclohexene ring; Or a substituted or unsubstituted tetrahydroethanonaphthalene ring is formed.
  • the groups are substituted or unsubstituted with one or more groups selected from the group consisting of deuterium, methyl group, ethyl group, propyl group, butyl group, and phenyl group, or a group to which two or more groups are bonded.
  • R1 or R2 when R1 or R2 is bonded to an adjacent group to form a substituted or unsubstituted ring, R1 or R2 is directly bonded to R3 or R5 to form a carbazole ring; Or it forms a hexahydrocarbazole ring, or is connected through B Includes the case of forming a ring.
  • the rings are substituted or unsubstituted.
  • the ring when R1 or R2 combines with an adjacent group to form a substituted or unsubstituted ring, the ring is represented by any one of the following formulas C1 to C3.
  • X21, X22 and X31 are the same as or different from each other, and each independently O; S; CP11P12; Or NP13,
  • P1 and P11 to P13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combined with an adjacent group to form a substituted or unsubstituted ring,
  • b1 is an integer of 1 to 3
  • p1 is an integer of 0 to 10
  • p2 and p3 are each an integer of 0 to 4,
  • X21 and X22 are the same as or different from each other, and each independently, O; S; Or CP11P12.
  • X31 is O; S; CP11P12; Or NP13.
  • P1 and P11 to P13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C30 alkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms by bonding with an adjacent group; Or a substituted or unsubstituted C 3 to C 30 aliphatic hydrocarbon ring is formed.
  • P1 and P11 to P13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 20 carbon atoms by bonding with an adjacent group; Or a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 carbon atoms.
  • P1 and P11 to P13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; An alkyl group unsubstituted or substituted with deuterium; It is a phenyl group, or combines with an adjacent group to form a benzene ring substituted or unsubstituted with an alkyl group substituted or unsubstituted with deuterium or deuterium, or a bicycloheptane ring or a bicyclooctane ring.
  • P1 and P11 to P13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium; An ethyl group unsubstituted or substituted with deuterium; A propyl group unsubstituted or substituted with deuterium; A butyl group unsubstituted or substituted with deuterium; Or a phenyl group, or a benzene ring unsubstituted or substituted with a methyl group unsubstituted or substituted with deuterium or deuterium by bonding to each other with an adjacent group, or a bicycloheptane ring or a bicyclooctane ring.
  • b1 is 1 or 2.
  • p1 is an integer of 1 to 6.
  • p1 is an integer of 1 to 4.
  • p2 and p3 are integers of 1 to 4.
  • R1 or R2 when R1 or R2 combines with an adjacent group to form a substituted or unsubstituted ring, it is represented by one of the following structures.
  • * means a position at which the formed ring is condensed, and the structures include deuterium; Or it is unsubstituted or substituted with a deuterium-substituted or unsubstituted alkyl group.
  • the structures are deuterium; Or a methyl group unsubstituted or substituted with deuterium; An ethyl group unsubstituted or substituted with deuterium; A propyl group unsubstituted or substituted with deuterium; Or substituted or unsubstituted with deuterium substituted or unsubstituted butyl group.
  • the structures are deuterium; Or a methyl group unsubstituted or substituted with deuterium; An ethyl group unsubstituted or substituted with deuterium; I-propyl group unsubstituted or substituted with deuterium; Or it is unsubstituted or substituted with a t-butyl group substituted or unsubstituted with deuterium.
  • the structures are deuterium; Or it is substituted or unsubstituted with CD 3.
  • Y is an alkyl group having 1 to 3 carbon atoms substituted with deuterium
  • at least one of X1, X2 and R1 to R5 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium.
  • Y is an alkyl group having 1 to 3 carbon atoms substituted with deuterium
  • at least one of R1 to R5 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium.
  • At least two of X1, X2, and R1 to R5 are an alkyl group having 1 to 3 carbon atoms substituted with deuterium.
  • At least three of X1, X2, and R1 to R5 are an alkyl group having 1 to 3 carbon atoms substituted with deuterium.
  • At least one of X1, X2, and R1 to R5 is a methyl group substituted with deuterium; An ethyl group substituted with deuterium; Or it is selected from a propyl group substituted with deuterium.
  • At least one of X1, X2, and R1 to R5 is a methyl group substituted with deuterium; An ethyl group substituted with deuterium; Or it is selected from i-propyl group substituted with deuterium.
  • At least two of X1, X2, and R1 to R5 are methyl groups substituted with deuterium; An ethyl group substituted with deuterium; Or it is selected from i-propyl group substituted with deuterium.
  • At least three of X1, X2, and R1 to R5 are methyl groups substituted with deuterium; An ethyl group substituted with deuterium; Or it is selected from i-propyl group substituted with deuterium.
  • At least two of R1 to R5 are an alkyl group having 1 to 3 carbon atoms substituted with deuterium.
  • At least three of R1 to R5 are an alkyl group having 1 to 3 carbon atoms substituted with deuterium.
  • At least one of R1 to R5 is -CD 3 ; -C 2 D 5 ; CH 2 CD 3 ; It is selected from CD(CD 3 ) 2 or CH(CD 3 ) 2 .
  • At least two of R1 to R5 are -CD 3 ; -C 2 D 5 ; CH 2 CD 3 ; It is selected from CD(CD 3 ) 2 or CH(CD 3 ) 2 .
  • At least three of R1 to R5 are -CD 3 ; -C 2 D 5 ; CH 2 CD 3 ; It is selected from CD(CD 3 ) 2 or CH(CD 3 ) 2 .
  • At least one of R1 to R5 is CD 3 .
  • At least two of R1 to R5 are CD 3 .
  • At least three of R1 to R5 are CD 3 .
  • R4 are the same or different and each is independently hydrogen or CD from each other - is 3 -
  • Chemical Formula 1 may be represented by Chemical Formula 101 below.
  • Y is an alkyl group having 1 to 3 carbon atoms substituted with deuterium; Or it is represented by the following formula 2.
  • Y is a methyl group substituted with deuterium; An ethyl group substituted with deuterium; Or it is a propyl group substituted with deuterium.
  • Y is a methyl group substituted with deuterium; An ethyl group substituted with deuterium; Or an i-propyl group substituted with deuterium.
  • Y is CDH 2 ; CD 2 H; CD 3 ; C 2 D 5 ; CH 2 CD 3 ; CD(CD 3 ) 2 ; Or CH(CD 3 ) 2 .
  • Y is -CD 3 ; -C 2 D 5 ; CH 2 CD 3 ; It is either CD(CD 3 ) 2 or CH(CD 3 ) 2 .
  • Y is CDH 2 ; It is either CD 2 H or CD 3.
  • Y is CD 3 .
  • Y is represented by the following formula (2).
  • B1 and B2 are the same as or different from each other, and each independently an aliphatic hydrocarbon ring; Or an aromatic hydrocarbon ring,
  • R6 and R7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkyl thioxy group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,
  • r6 and r7 are the same as or different from each other, and each independently an integer of 1 to 11, and when r6 and r7 are each 2 or more, the substituents in each parenthesis are the same or different from each other,
  • B1 and B2 are the same as or different from each other, and each independently a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms; Or a substituted or unsubstituted C6-C30 aromatic hydrocarbon ring.
  • B1 and B2 are the same as or different from each other, and each independently a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 carbon atoms; Or a substituted or unsubstituted C 6 to C 20 aromatic hydrocarbon ring.
  • B1 and B2 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic to tricyclic aliphatic hydrocarbon ring; Or a substituted or unsubstituted monocyclic to tricyclic aromatic hydrocarbon ring.
  • B1 and B2 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic aliphatic hydrocarbon ring; Or a substituted or unsubstituted monocyclic aromatic hydrocarbon ring.
  • B1 and B2 are the same as or different from each other, and each independently a substituted or unsubstituted benzene ring or a substituted or unsubstituted cyclohexane ring.
  • B1 and B2 are the same as or different from each other, and each independently a benzene ring or a cyclohexane ring unsubstituted or substituted with CD 3.
  • B1 and B2 are benzene rings.
  • B1 is a benzene ring
  • B2 is a cyclohexane ring unsubstituted or substituted with CD 3.
  • R6 and R7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C30 alkyl group; A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; A substituted or unsubstituted C 1 to C 30 alkyl thioxy group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms; A substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring having 12
  • R6 and R7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; A substituted or unsubstituted C 1 to C 20 alkyl thioxy group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms; A substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring having 12
  • R6 and R7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms; A substituted or unsubstituted C 1 to C 10 alkyl thioxy group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms; A substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted aryl group having 6 to 10 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 10 carbon atoms, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring having 12
  • R6 and R7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium; An ethyl group unsubstituted or substituted with deuterium; A propyl group unsubstituted or substituted with deuterium; A butyl group unsubstituted or substituted with deuterium; Trimethylsilyl group unsubstituted or substituted with deuterium; Or a phenyl group unsubstituted or substituted with deuterium or CD 3 , or R6 and R7 are bonded to each other to form a carbazole ring unsubstituted or substituted with a deuterium, methyl group, CD 3 or t-butyl group; Or cyclohexene unsubstituted or substituted with deuterium, methyl group, CD 3 or t-butyl group to form a hexahydro
  • R6 and R7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium; I-propyl group unsubstituted or substituted with deuterium; t-butyl group; Trimethylsilyl group; Or a phenyl group, R6 and R7 are bonded to each other to form a carbazole ring unsubstituted or substituted with a methyl group, CD 3 or t-butyl group; Or a methyl group, CD 3 or t-butyl group to form a substituted or unsubstituted hexahydrocarbazole ring, or to form a methyl group substituted or unsubstituted cyclohexene ring by bonding to each other with adjacent groups.
  • R6 and R7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium; I-propyl group unsubstituted or substituted with deuterium; t-butyl group; Trimethylsilyl group; Or, it is a phenyl group, or combines with an adjacent group to form the following structure.
  • the following structure is unsubstituted or substituted with deuterium, a methyl group unsubstituted or substituted with deuterium, an i-propyl group or t-butyl group substituted or unsubstituted with deuterium, Means a position bonded to the formula (1).
  • R6 and R7 are the same as or different from each other, and each independently hydrogen; Methyl group; CD 3 ; Or a t-butyl group, or R6 and R7 are bonded to each other to form a carbazole ring unsubstituted or substituted with a methyl group, CD 3 or t-butyl group; Or a methyl group, CD 3 or t-butyl group to form a substituted or unsubstituted hexahydrocarbazole ring.
  • R6 and R7 are the same as or different from each other, and each independently hydrogen; Or a t-butyl group, R6 and R7 are bonded to each other to CD 3 substituted or unsubstituted carbazole ring; Or CD 3 to form a substituted or unsubstituted hexahydrocarbazole ring.
  • Y when Y is represented by Formula 2, at least one of X1, X2 and R1 to R7 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium.
  • R1 to R7 when Y is represented by Formula 2, at least one of R1 to R7 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium.
  • At least two of X1, X2, and R1 to R7 are an alkyl group having 1 to 3 carbon atoms substituted with deuterium.
  • At least three of X1, X2, and R1 to R7 are an alkyl group having 1 to 3 carbon atoms substituted with deuterium.
  • At least one of X1, X2, and R1 to R7 is a methyl group substituted with deuterium; An ethyl group substituted with deuterium; Or it is selected from a propyl group substituted with deuterium.
  • At least one of X1, X2, and R1 to R7 is a methyl group substituted with deuterium; An ethyl group substituted with deuterium; Or it is selected from i-propyl group substituted with deuterium.
  • At least two of X1, X2, and R1 to R7 are methyl groups substituted with deuterium; An ethyl group substituted with deuterium; Or it is selected from i-propyl group substituted with deuterium.
  • At least three of X1, X2, and R1 to R7 are methyl groups substituted with deuterium; An ethyl group substituted with deuterium; Or it is selected from i-propyl group substituted with deuterium.
  • At least two of R1 to R7 are an alkyl group having 1 to 3 carbon atoms substituted with deuterium.
  • At least three of R1 to R7 are an alkyl group having 1 to 3 carbon atoms substituted with deuterium.
  • At least one of R1 to R7 is -CD 3 ; -C 2 D 5 ; CH 2 CD 3 ; It is selected from CD(CD 3 ) 2 or CH(CD 3 ) 2 .
  • At least two of R1 to R7 are -CD 3 ; -C 2 D 5 ; CH 2 CD 3 ; It is selected from CD(CD 3 ) 2 or CH(CD 3 ) 2 .
  • At least three of R1 to R7 are -CD 3 ; -C 2 D 5 ; CH 2 CD 3 ; It is selected from CD(CD 3 ) 2 or CH(CD 3 ) 2 .
  • At least one of R1 to R7 is CD 3 .
  • At least two of R1 to R7 are CD 3 .
  • At least three of R1 to R7 are CD 3 .
  • r1 and r2 are the same as or different from each other, and are each independently an integer of 1 to 3.
  • r1 and r2 are the same as or different from each other, and are each independently 1 or 2.
  • r3 and r5 to r7 are the same as or different from each other, and are each independently an integer of 1 to 11.
  • r3 and r5 to r7 are the same as or different from each other, and are each independently an integer of 1 to 9.
  • r3 and r5 to r7 are the same as or different from each other, and are each independently an integer of 1 to 5.
  • r3 and r5 to r7 are the same as or different from each other, and are each independently an integer of 1 to 3.
  • r4 is an integer of 1 or 2.
  • r4 is 1.
  • r4 is 2.
  • n is an integer of 1 or 2.
  • n 1
  • n is 2.
  • r4+n is an integer of 2 or 3.
  • Formula 2 ( ) Is represented by any one of the following Chemical Formulas 201 to 203.
  • G6 and G7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkyl thioxy group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combined with an adjacent group to form a substituted or unsubstituted ring,
  • G16 and G17 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group,
  • g6 and g7 are each an integer of 1 to 5, g6' and g7' are an integer of 1 to 4, and g7'' is an integer of 1 to 8,
  • G6 and G7 are the same as those of R6 and R7 described above.
  • G16 and G17 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted C 1 to C 20 alkyl group.
  • G16 and G17 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted C 1 to C 10 alkyl group.
  • G16 and G17 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or an alkyl group unsubstituted or substituted with deuterium.
  • G16 and G17 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a methyl group unsubstituted or substituted with deuterium.
  • G16 and G17 are methyl groups or CD 3 .
  • Chemical Formula 2 is represented by any one of the following structural formulas.
  • g6, g7, g6', g7', and g7'' are integers of 1 to 4, respectively.
  • g6, g7, g6', g7', and g7'' are integers of 1 to 3, respectively.
  • g6, g7, g6', g7', and g7'' are 1 or 2, respectively.
  • Chemical Formula 1 is represented by the following Chemical Formula 1-1 or 1-2.
  • R1 to R7 A1, A2, B1, B2, X1, X2 and r1 to r7 are the same as those in Formula 1,
  • Z is an alkyl group having 1 to 3 carbon atoms substituted with deuterium
  • n is an integer of 1 or 2
  • Z is the same as or different from each other
  • r4+m is an integer of 2 or 3.
  • Z is a methyl group substituted with deuterium; An ethyl group substituted with deuterium; Or it is a propyl group substituted with deuterium.
  • Z is a methyl group substituted with deuterium; An ethyl group substituted with deuterium; Or an i-propyl group substituted with deuterium.
  • Z is a methyl group substituted with deuterium.
  • Z is CDH 2 ; It is either CD 2 H or CD 3.
  • Z is CD 3 .
  • m is an integer of 1 or 2.
  • m is 1.
  • m is 2.
  • At least one of X1, X2, and R1 to R5 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium.
  • At least one of R1 to R5 in Formula 1-1 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium.
  • At least one of X1, X2, and R1 to R7 in Formula 1-2 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium.
  • At least one of R1 to R7 in Formula 1-2 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium.
  • Formula 1 is represented by any one of the following Formulas 1-3 to 1-7.
  • R1 to R7, X1, X2 and r1 to r7 are the same as those in Formula 1,
  • Z is an alkyl group having 1 to 3 carbon atoms substituted with deuterium
  • n is an integer of 1 or 2, and when m is 2, Z is the same as or different from each other.
  • Chemical Formula 1 is represented by the following Chemical Formula 1-8.
  • A1, A2, R1 to R5, r1 to r5, Y and n are the same as those in Formula 1,
  • X3 is CRaRb, NRc, O, PRd, S, PORe, SO 2 , SiRfRg or BRh,
  • Ra To Rh are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring.
  • Ra to Rh in Formula 1-8 is the same as the definition of Ra to Rh in Formula 1.
  • Chemical Formula 1 is represented by the following Chemical Formula 1-9 or 1-10.
  • X1, X2, A1, A2, R1, R3 to R5, r1, r3 to r5, Y and n are the same as those in Formula 1,
  • A3 and A4 are the same as or different from each other, and each independently a substituted or unsubstituted aliphatic hydrocarbon ring; A substituted or unsubstituted aromatic hydrocarbon ring; Substituted or unsubstituted aromatic heterocycle; Or a condensed ring of a substituted or unsubstituted aliphatic hydrocarbon ring and an aromatic hydrocarbon ring,
  • R21 and R22 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combined with an adjacent group to form a substituted or unsubstituted ring,
  • r21 and r22 are each an integer of 1 to 9,
  • R21 and R22 are each 2 or more, two or more R21 and R22 are each the same as or different from each other.
  • A3 is represented by any one of the following structural formulas.
  • the definition of a case where R1 or R2 is bonded to each other to form a substituted or unsubstituted ring is applied to A3 and A4.
  • A3 and A4 are the same as or different from each other, and are each independently represented by any one of the following structures.
  • * means a position at which the formed ring is condensed, and the structures include deuterium; Or it is unsubstituted or substituted with a deuterium-substituted or unsubstituted alkyl group.
  • Chemical Formula 1 is represented by the following Chemical Formulas 1-11 or 1-12.
  • X1, X2, R1 to R5, r1, r3, r4, A1, Y and n are the same as those in Formula 1,
  • X101 is a direct bond; Or -BR103-,
  • R103, G101 and G102 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
  • r2' is 1 or 2
  • r5' is an integer from 1 to 4,
  • r5'' is an integer from 1 to 8
  • R2 and R5 are each 2 or more, two or more R2 and R5 are each the same as or different from each other.
  • Formula 1 is represented by any one of the following compounds.
  • compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure as described above.
  • the HOMO and LUMO energy levels of the compound can be adjusted by introducing various substituents to the core structure of the above structure.
  • the compound of Formula 1 of the present invention may have a core structure as shown in the following scheme. Substituents may be bonded by methods known in the art, and the type, position, and number of substituents may be changed according to techniques known in the art.
  • Y is an alkyl group having 1 to 3 carbon atoms substituted with deuterium; Or a substituted or unsubstituted amine group, and n is 1 to 3.
  • Y is an alkyl group having 1 to 3 carbon atoms substituted with deuterium; Or a substituted or unsubstituted amine group, and n is 1 to 3.
  • a deuterium substituted methyl group may be introduced from [Intermediate 3], which is a boron compound containing a methyl group, using a deuterium substitution reaction using a transition metal catalyst.
  • Intermediate 3 is a boron compound containing a methyl group, using a deuterium substitution reaction using a transition metal catalyst.
  • Reaction Scheme 3 a chemical substance having a methyl group at a specific position is illustrated, but a deuterium substituted alkyl group may be introduced by replacing the C-H bond of the alkyl groups present at various positions of the boron compound in addition to the methyl group to a C-D bond with a substitution rate of 15% or more.
  • the conjugation length and energy band gap of the aforementioned chemicals are closely related. Specifically, the longer the conjugation length of the chemical, the smaller the energy band gap.
  • compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure as described above.
  • the HOMO and LUMO energy levels of the compound are adjusted, and the CH bond of the methyl group among the introduced substituents is changed to a harder CD bond, thereby optical properties and lifetime.
  • Compounds with improved properties can be synthesized.
  • the present specification provides an organic light-emitting device including the above-described compound.
  • the first electrode A second electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound.
  • the organic material layer of the organic light emitting device of the present specification may have a single-layer structure, but may have a multilayer structure in which two or more organic material layers are stacked.
  • the organic light emitting device may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, etc. as an organic material layer. have.
  • the structure of the organic light emitting device is not limited thereto, and may include a smaller number of organic material layers.
  • the organic material layer includes an emission layer
  • the emission layer includes the compound represented by Formula 1 above.
  • the organic material layer includes an emission layer
  • the emission layer includes the compound represented by Formula 1 as a dopant of the emission layer.
  • the organic material layer includes an emission layer
  • the emission layer includes the compound represented by Formula 1 as a blue fluorescent dopant of the emission layer.
  • the organic material layer includes a hole injection layer or a hole transport layer
  • the hole injection layer or the hole transport layer includes the compound represented by Formula 1 above.
  • the organic material layer includes an electron injection layer, an electron transport layer, or a layer that simultaneously injects and transports electrons
  • the electron injection layer, the electron transport layer, or a layer that simultaneously injects and transports electrons is the formula Including the compound represented by 1.
  • the organic material layer includes an electron blocking layer
  • the electron blocking layer includes the compound represented by Formula 1 above.
  • the organic material layer includes a hole blocking layer
  • the hole blocking layer includes a compound represented by Formula 1 above.
  • the organic light emitting device is a hole injection layer and a hole transport layer. It further includes one or two or more layers selected from the group consisting of a light-emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer.
  • the emission layer further includes a host compound.
  • the emission layer further includes a host compound, and the host compound is one in which at least one hydrogen is substituted with deuterium.
  • the host compound when the host compound is substituted with deuterium, 30% or more is substituted with deuterium. In another exemplary embodiment, the host compound is substituted by 40% or more with deuterium. In another exemplary embodiment, the host compound is substituted with deuterium by at least 60%. In another exemplary embodiment, the host compound is 80% or more substituted with deuterium. In another exemplary embodiment, the host compound is 100% substituted with deuterium.
  • the emission layer further includes a compound represented by the following formula (H).
  • L20 and L21 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
  • Ar20 and Ar21 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • R20 is hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • r20 is an integer from 0 to 8, and when r20 is 2 or more, R20 is the same as or different from each other.
  • L20 and L21 are the same as or different from each other, and each independently a direct bond; An arylene group having 6 to 40 carbon atoms; Or it is a C6-C40 divalent heterocyclic group.
  • L20 and L21 are the same as or different from each other, and each independently a direct bond; An arylene group having 6 to 20 carbon atoms; Or a divalent heterocyclic group having 6 to 20 carbon atoms.
  • L20 and L21 are the same as or different from each other, and each independently a direct bond; Phenylene group; Biphenylene group; Naphthylene group; Divalent dibenzofuran group; Or a divalent dibenzothiophene group.
  • Ar20 and Ar21 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C2 to C60 heterocyclic group.
  • Ar20 and Ar21 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heterocyclic group.
  • Ar20 and Ar21 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic to tetracyclic aryl group; Or a substituted or unsubstituted monocyclic to 4 ring heterocyclic group.
  • Ar20 and Ar21 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted anthracene group; A substituted or unsubstituted phenanthryl group; A substituted or unsubstituted phenalene group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted benzofluorenyl group; A substituted or unsubstituted furan group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted naphthobenzofuran group; A substituted or unsub
  • Ar20 and Ar21 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms; A biphenyl group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms; A naphthyl group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms; A dibenzofuran group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms; A naphthobenzofuran group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms; A dibenzothiophene group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms; Or a naphthobenzothiophene group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms
  • Ar20 is a substituted or unsubstituted heterocyclic group
  • Ar21 is a substituted or unsubstituted aryl group.
  • Ar20 and Ar21 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with deuterium; A naphthyl group unsubstituted or substituted with deuterium; Or a dibenzofuran group unsubstituted or substituted with deuterium.
  • R20 is hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted C1-C30 alkyl group; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C2 to C60 heteroaryl group.
  • R20 is hydrogen; heavy hydrogen; Fluorine group; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted C 3 to C 10 cycloalkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heteroaryl group.
  • R20 is hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heteroaryl group.
  • R20 is hydrogen; heavy hydrogen; A substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group.
  • R20 is hydrogen; heavy hydrogen; Or a naphthyl group unsubstituted or substituted with deuterium.
  • r20 is an integer of 1 to 8.
  • Chemical Formula H may include at least one deuterium.
  • Chemical Formula H is represented by the following Chemical Formula I or J.
  • the structure of Formula H when the compound represented by Formula H is substituted with deuterium, 30% or more is substituted with deuterium. In another exemplary embodiment, the structure of Formula H is substituted by 40% or more with deuterium. In another exemplary embodiment, the structure of Formula H is substituted with deuterium by at least 60%. In another exemplary embodiment, the structure of Formula H is substituted with deuterium by 80% or more. In another exemplary embodiment, the structure of Formula H is 100% substituted with deuterium.
  • the compound represented by Formula H is any one selected from the following compounds.
  • the compound represented by Formula 1 is used as a dopant, and the compound represented by Formula H is used as a host.
  • the content of the dopant may be selected from 0.01 to 10 parts by weight based on 100 parts by weight of the host, but is not limited thereto.
  • the emission layer further includes two or more host compounds.
  • the content of the host may be 10:90 to 90:10 based on a first host: a second host.
  • the content between the hosts may be 20:80 to 80:20, and in another example, it may be 40:60 to 60:40.
  • the light-emitting layer may further include a host material, and the host may include a condensed aromatic ring derivative or a heterocyclic-containing compound.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, triazine derivatives, and the like, and may be a mixture of two or more thereof, but are not limited thereto.
  • the organic light emitting device includes a first electrode; A second electrode; A light emitting layer provided between the first electrode and the second electrode; And two or more organic material layers provided between the light-emitting layer and the first electrode or between the light-emitting layer and the second electrode, and at least one of the two or more organic material layers includes a compound represented by Formula 1 above.
  • two or more organic material layers may be selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, a layer for simultaneously transporting and injecting holes, and an electron blocking layer.
  • the organic material layer includes two or more electron transport layers, and at least one of the two or more electron transport layers includes a compound represented by Formula 1 above.
  • the compound represented by Formula 1 may be included in one of the two or more electron transport layers, and may be included in each of two or more electron transport layers.
  • materials other than the compound represented by Formula 1 may be the same or different from each other.
  • the electron transport layer may further include an n-type dopant.
  • the n-type dopant those known in the art may be used, for example, a metal or a metal complex.
  • the electron transport layer including the compound represented by Formula 1 may further include LiQ (Lithium Quinolate).
  • the organic material layer includes two or more hole transport layers, and at least one of the two or more hole transport layers includes a compound represented by Formula 1 above.
  • the compound represented by Formula 1 may be included in one of the two or more hole transport layers, and may be included in each of two or more hole transport layers.
  • the organic material layer further comprises a hole injection layer or a hole transport layer including a compound including an arylamine group, a carbazolyl group, or a benzocarbazolyl group in addition to the organic material layer including the compound represented by Formula 1 Can include.
  • the first electrode is an anode or a cathode.
  • the second electrode is a cathode or an anode.
  • the organic light-emitting device may be a normal type organic light-emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting device may be an inverted type organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
  • FIGS. 1 and 2 illustrate an organic light-emitting device and are not limited thereto.
  • FIG. 1 illustrates a structure of an organic light-emitting device in which a substrate 1, an anode 2, an emission layer 7 and a cathode 11 are sequentially stacked.
  • the compound may be included in the emission layer 3.
  • the compound includes the first hole injection layer 3, the second hole injection layer 4, the hole transport layer 5, the electron blocking layer 6, the light emitting layer 7, and the first electron transport layer ( 8), it may be included in one or more of the second electron transport layer 9 and the electron injection layer 10.
  • the organic light-emitting device of the present specification may be manufactured by materials and methods known in the art, except that at least one of the organic material layers includes the compound, that is, the compound represented by Formula 1.
  • the organic material layers may be formed of the same material or different materials.
  • the organic light emitting device of the present specification may be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate.
  • a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation
  • a metal or a conductive metal oxide or an alloy thereof is deposited on the substrate to form an anode.
  • It can be manufactured by forming and forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.
  • an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the compound represented by Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device.
  • the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.
  • an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate (International Patent Application Publication No. 2003/012890).
  • the manufacturing method is not limited thereto.
  • the first electrode material a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer.
  • metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof;
  • Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO);
  • a combination of a metal and an oxide such as ZnO:Al or SnO 2 :Sb;
  • Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.
  • the second electrode material is generally preferably a material having a small work function so that electrons can be easily injected into the organic material layer.
  • Metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof;
  • There are a multi-layered material such as LiF/Al or LiO 2 /Al, but are not limited thereto.
  • the emission layer may include a host material and a dopant material.
  • the host material include condensed aromatic ring derivatives or heterocyclic-containing compounds.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • heterocycle-containing compounds include dibenzofuran derivatives, ladder furan compounds, And pyrimidine derivatives, but are not limited thereto.
  • the dopant material examples include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes in addition to the compound represented by Formula 1 above.
  • the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamine group, and includes pyrene, anthracene, chrysene, periflanthene and the like having an arylamine group.
  • the styrylamine compound is a compound in which at least one arylvinyl group is substituted with a substituted or unsubstituted arylamine, and is selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group. Substituents are substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, and styryltetraamine, but are not limited thereto.
  • examples of the metal complex include an iridium complex and a platinum complex, but are not limited thereto.
  • the emission material of the emission layer is formed by transporting and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively.
  • a material capable of emitting light in the visible region a material having good quantum efficiency for fluorescence or phosphorescence is preferable.
  • 8-hydroxy-quinoline aluminum complex Alq3
  • Carbazole-based compounds Dimerized styryl compounds
  • BAlq 10-hydroxybenzoquinoline-metal compound
  • Benzoxazole, benzthiazole, and benzimidazole-based compounds Poly(p-phenylenevinylene) (PPV)-based polymer
  • Spiro compounds Polyfluorene; And rubrene, but are not limited thereto.
  • the hole injection layer is a layer for injecting holes from an electrode. It is preferable that the hole injection material has the ability to transport holes and thus has a hole injection effect in the first electrode and an excellent hole injection effect in the light emitting layer or the light emitting material. In addition, a material having excellent ability to prevent movement of excitons generated in the light emitting layer to the electron injection layer or the electron injection material is preferable. In addition, a material excellent in thin film formation ability is preferred. In addition, it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the first electrode material and the HOMO of the surrounding organic material layer.
  • the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material; Carbazole-based organic matter; Nitrile-based organics; Hexanitrile hexaazatriphenylene-based organic material; Quinacridone series organic matter; Perylene-based organics; Polythiophene-based conductive polymers such as anthraquinone and polyaniline, or a mixture of two or more of the above examples, but are not limited thereto.
  • the hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the emission layer.
  • the hole transporting material is a material capable of transporting holes from the first electrode or the hole injection layer and transferring them to the light emitting layer, and a material having high mobility for holes is preferable. Specific examples include, but are not limited to, an arylamine-based organic material, a carbazole-based organic material, a conductive polymer, and a block copolymer including a conjugated portion and a non-conjugated portion.
  • the electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer.
  • the electron transport material is a material capable of receiving electrons from the second electrode and transferring them to the light emitting layer, and a material having high mobility for electrons is preferable. Specific examples include Al complex of 8-hydroxyquinoline; Complexes containing Alq3; Organic radical compounds; Hydroxyflavone-metal complex; Triazine derivatives; LiQ and the like, but are not limited thereto.
  • the electron transport layer can be used with any desired first electrode material, as used according to the prior art.
  • a suitable first electrode material has a low work function and is a conventional material followed by an aluminum layer or a silver layer. Specifically, there are cesium, barium, calcium, ytterbium and samarium, and in each case, an aluminum layer or a silver layer follows.
  • the electron injection layer is a layer that injects electrons from an electrode. It is preferable that the electron injection material is excellent in the ability to transport electrons, and has an electron injection effect from the second electrode and an excellent electron injection effect on the light-emitting layer or the light-emitting material. In addition, a material that prevents excitons generated in the light emitting layer from moving to the hole injection layer and has excellent thin film formation ability is preferable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, triazine, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc.
  • metal complex compounds and nitrogen-containing 5-membered ring derivatives and mixtures of two or more of the above examples, but are not limited thereto.
  • 8-hydroxyquinolinato lithium bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese , Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h) ]Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato) (o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc. , But is not limited thereto.
  • the electron blocking layer is a layer capable of improving the lifespan and efficiency of a device by preventing holes injected from the hole injection layer from entering the electron injection layer through the emission layer.
  • Known materials may be used without limitation, and may be formed between the light-emitting layer and the hole injection layer, or between the light-emitting layer and a layer that simultaneously injects and transports holes.
  • the hole blocking layer is a layer that prevents holes from reaching the second electrode, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, aluminum complexes, pyridine, pyrimidine or triazine derivatives, but are not limited thereto.
  • the organic light-emitting device may be a top emission type, a bottom emission type, or a double-sided emission type depending on the material used.
  • the compound represented by Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.
  • the compound according to the present specification may act on a principle similar to that applied to an organic light-emitting device in an organic light-emitting device including an organic phosphorescent device, an organic solar cell, an organic photoreceptor, and an organic transistor.
  • the organic solar cell may have a structure including a negative electrode, a positive electrode, and a photoactive layer provided between the negative electrode and the positive electrode, and the photoactive layer may include the compound.
  • a glass substrate coated with a thin film of 1,400 ⁇ of ITO (indium tin oxide) was placed in distilled water dissolved in a detergent and washed with ultrasonic waves.
  • Fischer Co. product was used as a detergent, and distilled water secondarily filtered with a filter made by Millipore Co. was used as distilled water.
  • ultrasonic washing was performed for 10 minutes by repeating twice with distilled water.
  • ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner.
  • the substrate was transported to a vacuum evaporator.
  • the following HI-A and HI-B were thermally vacuum deposited to a thickness of 650 ⁇ and 50 ⁇ , respectively, to form a first hole injection layer and a second hole injection layer.
  • the following HT-A was vacuum deposited to a thickness of 600 ⁇ to form a hole transport layer.
  • the following HT-B was vacuum deposited to a thickness of 50 ⁇ to form an electron blocking layer.
  • a light emitting layer was formed by vacuum deposition of Compound 1 as a blue light-emitting dopant on the electron blocking layer to a thickness of 4 wt% based on the total weight of the light-emitting layer and BH-1 as a host to a thickness of 96 wt% and 200 ⁇ based on the total weight of the light-emitting layer.
  • ET-A was vacuum-deposited on the light-emitting layer as a first electron transport layer, and subsequently ET-B and LiQ were vacuum-deposited at a 1:1 weight ratio to form a second electron transport layer having a thickness of 360 ⁇ .
  • LiQ was vacuum-deposited on the second electron transport layer and vacuum-deposited to a thickness of 5 ⁇ to form an electron injection layer.
  • the deposition rate of organic materials was maintained at 0.4 ⁇ 0.9 ⁇ /sec, and the deposition rate of aluminum at the cathode was maintained at 2 ⁇ /sec, and the vacuum degree during deposition was 1 ⁇ 10 -7 ⁇ 5 ⁇ 10 -8 torr.
  • the vacuum degree during deposition was 1 ⁇ 10 -7 ⁇ 5 ⁇ 10 -8 torr.
  • Example 1 Examples 2 to 20 and Comparative Examples 1 to 1 were used in the same manner as in Example 1, except that the compounds shown in Table 1 were used instead of Compounds 1 and BH-1 as the dopant and host of the emission layer. Each of the organic light emitting devices of 4 was manufactured.
  • T 95 represents the ratio of the time required for the luminance to decrease to 95% when the initial luminance at a current density of 20 mA/cm 2 is 100%, based on Comparative Example 1.
  • Example 1 the same method as in Example 1 was used, except that the compound shown in Table 2 was used instead of the compound 1 as the dopant of the light emitting layer, and the compound shown in Table 2 was used as the host of the light emitting layer.
  • Organic light emitting devices of Examples 21 to 24 and Comparative Example 5 were fabricated, respectively.
  • the weight ratio of the first host and the second host of the emission layer is 50:50.
  • T 95 represents the ratio of the time required for the luminance to decrease to 95% when the initial luminance at a current density of 20 mA/cm 2 is 100%, based on Comparative Example 1.
  • the conversion efficiency (cd/A/y) considers from the current efficiency (cd/A) to the color purity (CIEy) of the material, and becomes an important efficiency reference value in small and large organic light emitting devices aiming at high luminance and high color reproducibility. .
  • the organic light emitting device was constructed using a dopant material including an alkyl group having 1 to 3 carbon atoms substituted with deuterium represented by [Chemical Formula 1] according to an exemplary embodiment of the present specification. At that time, both the conversion efficiency and lifetime performance of the device were superior to those of the other devices.
  • the compound of Formula 1 of the present invention is characterized in that an alkyl group substituted with deuterium is bonded at a specific position, and the efficiency is up to about 10% compared to the comparative compounds BD-A, BD-C and BD-D that are not otherwise. The results were high, and the lifespan was 2 to 3 times higher.
  • the compound of Formula 1 including an alkyl group having 1 to 3 carbon atoms substituted with deuterium exhibited excellent effects in efficiency and life as compared to Comparative Example BD-B including a butyl group substituted with deuterium.
  • methyl radical, ethyl radical, and propyl radical which are alkyl radicals having 1 to 3 carbon atoms, are unstable compared to the butyl radical, which is a tertiary carbon radical (more than 4 carbon atoms), and the C(sp 3 )-C(sp 2 ) bond is destroyed This is because the decomposition process of the compound that occurs is relatively suppressed, and the stability of the compound structure is ensured.

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Abstract

The present specification provides a compound represented by chemical formula 1, and an organic light-emitting device comprising same.

Description

화합물 및 이를 포함하는 유기 발광 소자Compound and organic light-emitting device comprising the same

본 출원은 2019년 9월 10일에 한국특허청에 제출된 한국 특허 출원 제10-2019-0112000호의 출원일의 이익을 주장하며, 그 내용 전부는 본 명세서에 포함된다.This application claims the benefit of the filing date of Korean Patent Application No. 10-2019-0112000 filed with the Korean Intellectual Property Office on September 10, 2019, the entire contents of which are incorporated herein.

본 명세서는 중수소로 치환된 알킬기를 포함하는 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다. The present specification relates to a compound including an alkyl group substituted with deuterium and an organic light emitting device including the same.

일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기 발광 소자는 통상 양극과 음극 및 이 사이에 유기물층을 포함하는 구조를 가진다. 여기서 유기물층은 유기 발광 소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 등으로 이루어 질 수 있다. 이러한 유기 발광 소자의 구조에서 두 전극 사이에 전압을 걸어주게 되면 양극에서는 정공이, 음극에서는 전자가 유기물층에 주입되게 되고, 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 다시 바닥상태로 떨어질 때 빛이 나게 된다. In general, the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy by using an organic material. An organic light emitting device using the organic light emitting phenomenon has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer is often made of a multilayer structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device.For example, it may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of such an organic light emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. When it falls back to the ground, it glows.

상기와 같은 유기 발광 소자를 위한 새로운 재료의 개발이 계속 요구되고 있다.Development of a new material for the organic light emitting device as described above is continuously required.

[선행기술문헌][Prior technical literature]

(특허문헌 1) 중국 특허 공개 108586441(Patent Document 1) Chinese Patent Publication 108586441

본 명세서에서는 중수소로 치환된 알킬기를 포함하는 화합물 및 이를 포함하는 유기 발광 소자를 제공한다. In the present specification, a compound including an alkyl group substituted with deuterium and an organic light emitting device including the same are provided.

본 명세서의 일 실시상태는 하기 화학식 1로 표시되는 화합물을 제공한다.An exemplary embodiment of the present specification provides a compound represented by Formula 1 below.

[화학식 1][Formula 1]

Figure PCTKR2020012249-appb-I000001
Figure PCTKR2020012249-appb-I000001

상기 화학식 1에 있어서, In Formula 1,

A1 및 A2는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 지방족 탄화수소고리; 치환 또는 비치환된 방향족 탄화수소고리; 치환 또는 비치환된 방향족 헤테로고리; 또는 치환 또는 비치환된 지방족 탄화수소고리 및 방향족 탄화수소고리의 축합고리이고,A1 and A2 are the same as or different from each other, and each independently a substituted or unsubstituted aliphatic hydrocarbon ring; A substituted or unsubstituted aromatic hydrocarbon ring; Substituted or unsubstituted aromatic heterocycle; Or a condensed ring of a substituted or unsubstituted aliphatic hydrocarbon ring and an aromatic hydrocarbon ring,

X1 및 X2는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 또는 치환 또는 비치환된 알킬기이거나, -CRaRb-, -NRc-, -O-, -PRd-, -S-, -PORe-, -SO2-, -SiRfRg-, 또는 -BRh-를 통해 직접 연결되고, X1 and X2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group, or directly linked through -CRaRb-, -NRc-, -O-, -PRd-, -S-, -PORe-, -SO 2 -, -SiRfRg-, or -BRh- Become,

Ra 내지 Rh는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 알키닐기; 치환 또는 비치환된 아릴알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 인접하는 기는 서로 결합하여 치환 또는 비치환된 고리를 형성하고,Ra To Rh are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,

R1 내지 R5는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아릴티옥시기; 치환 또는 비치환된 알킬티오기; 치환 또는 비치환된 아릴티오기; 치환 또는 비치환된 알킬술포닐기; 치환 또는 비치환된 아릴술포닐기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 알키닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 아릴알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 인접하는 기는 서로 결합하여 치환 또는 비치환된 고리를 형성하고,R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkyl thioxy group; A substituted or unsubstituted arylthioxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfonyl group; A substituted or unsubstituted arylsulfonyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,

Y는 중수소로 치환된 탄소수 1 내지 3의 알킬기; 또는 하기 화학식 2로 표시되고,Y is an alkyl group having 1 to 3 carbon atoms substituted with deuterium; Or represented by the following formula (2),

[화학식 2][Formula 2]

Figure PCTKR2020012249-appb-I000002
Figure PCTKR2020012249-appb-I000002

상기 화학식 2에 있어서,In Formula 2,

B1 및 B2는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 지방족 탄화수소 고리; 또는 치환 또는 비치환된 방향족 탄화수소 고리이고,B1 and B2 are the same as or different from each other, and each independently a substituted or unsubstituted aliphatic hydrocarbon ring; Or a substituted or unsubstituted aromatic hydrocarbon ring,

R6 및 R7은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 알키닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 아릴알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 인접하는 기는 서로 결합하여 치환 또는 비치환된 고리를 형성하고,R6 and R7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkyl thioxy group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,

r1 및 r2는 서로 동일하거나 상이하고, 각각 독립적으로 1 내지 3의 정수이고,r1 and r2 are the same as or different from each other, and each independently an integer of 1 to 3,

r3 및 r5 내지 r7는 서로 동일하거나 상이하고, 각각 독립적으로 1 내지 11의 정수이고,r3 and r5 to r7 are the same as or different from each other, and each independently an integer of 1 to 11,

r4는 1 또는 2의 정수이고,r4 is an integer of 1 or 2,

n은 1 또는 2의 정수이고,n is an integer of 1 or 2,

r4+n는 2 또는 3의 정수이고,r4+n is an integer of 2 or 3,

r1 내지 r7 및 n이 각각 2 이상인 경우, 각각의 괄호 안의 치환기는 서로 동일하거나 상이하고,When r1 to r7 and n are each 2 or more, the substituents in each parenthesis are the same as or different from each other,

Y가 중수소로 치환된 탄소수 1 내지 3의 알킬기인 경우, X1, X2 및 R1 내지 R5 중 적어도 하나는 중수소로 치환된 탄소수 1 내지 3의 알킬기이고,When Y is an alkyl group having 1 to 3 carbon atoms substituted with deuterium, at least one of X1, X2 and R1 to R5 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium,

Y가 상기 화학식 2로 표시되는 경우, X1, X2 및 R1 내지 R7 중 적어도 하나는 중수소로 치환된 탄소수 1 내지 3의 알킬기이고,When Y is represented by Formula 2, at least one of X1, X2 and R1 to R7 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium,

Figure PCTKR2020012249-appb-I000003
는 화학식 1에 결합되는 위치를 의미한다.
Figure PCTKR2020012249-appb-I000003
Means a position bonded to the formula (1).

또한, 본 명세서의 일 실시상태에 따르면, 제1 전극; 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 상기 화학식 1로 표시되는 화합물을 포함하는 것인 유기 발광 소자를 제공한다.In addition, according to an exemplary embodiment of the present specification, the first electrode; A second electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound represented by Formula 1 do.

본 명세서에 기재된 화합물은 유기 발광 소자의 유기물층의 재료로서 사용될 수 있다. 적어도 하나의 실시상태에 따른 화합물은 유기 발광 소자에서 효율의 향상, 낮은 구동전압 및/또는 수명 특성을 향상시킬 수 있다. 특히, 본 명세서에 기재된 화합물은 정공주입, 정공수송, 정공주입과 정공수송, 전자차단, 발광, 정공차단, 전자수송, 또는 전자주입 재료로 사용될 수 있다. 또한, 기존 유기 발광 소자에 비하여, 낮은 구동전압, 고효율 또는 장수명의 효과가 있다.The compounds described herein can be used as a material for an organic material layer of an organic light-emitting device. The compound according to at least one exemplary embodiment may improve efficiency, low driving voltage, and/or improve lifespan characteristics in an organic light-emitting device. In particular, the compounds described herein may be used as a hole injection, hole transport, hole injection and hole transport, electron blocking, light emission, hole blocking, electron transport, or electron injection material. In addition, compared to the existing organic light emitting device, there is an effect of a low driving voltage, high efficiency, or long life.

또한, 본원 화학식 1은 중수소로 치환된 알킬기를 포함함으로써, 화합물의 공액 및 안정성을 개선시키는 효과가 있다.In addition, the present Chemical Formula 1 has an effect of improving the conjugation and stability of the compound by including an alkyl group substituted with deuterium.

도 1은 기판(1), 양극(2), 발광층(7) 및 음극(11)이 순차적으로 적층된 유기 발광 소자의 예를 도시한 것이다. 1 shows an example of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 7 and a cathode 11 are sequentially stacked.

도 2는 기판(1), 양극(2), 제1 정공주입층(3), 제2 정공주입층(4), 정공수송층(5), 전자차단층(6), 발광층(7), 제1 전자수송층(8), 제2 전자수송층(9), 전자주입층(10) 및 음극(11)이 순차적으로 적층된 유기 발광 소자의 예를 도시한 것이다.2 shows a substrate 1, an anode 2, a first hole injection layer 3, a second hole injection layer 4, a hole transport layer 5, an electron blocking layer 6, a light emitting layer 7, and An example of an organic light-emitting device in which the first electron transport layer 8, the second electron transport layer 9, the electron injection layer 10, and the cathode 11 are sequentially stacked is shown.

[부호의 설명][Explanation of code]

1: 기판1: substrate

2: 양극2: anode

3: 제1 정공주입층3: first hole injection layer

4: 제2 정공주입층4: second hole injection layer

5: 정공수송층5: hole transport layer

6: 전자차단층6: Electron blocking layer

7: 발광층7: light emitting layer

8: 제1 전자수송층8: first electron transport layer

9: 제2 전자수송층9: second electron transport layer

10: 전자주입층10: electron injection layer

11: 음극11: cathode

이하 본 명세서에 대하여 더욱 상세히 설명한다. Hereinafter, the present specification will be described in more detail.

기존의 보론 화합물은 반치폭이 23nm 내지 30nm 정도이고, 기본 코어구조의 파장은 453nm 정도이나, 물질의 안정성이 아민 화합물에 비해 상대적으로 떨어져 수명이 낮아지는 한계를 가지고 있다. 따라서, 보론 화합물의 치환기 조절을 통해 우수한 광학적 특성을 유지하면서 물질의 안정성을 높여 긴 수명을 확보하는 방법이 요구된다.Existing boron compounds have a half width of about 23 nm to 30 nm, and the wavelength of the basic core structure is about 453 nm, but the stability of the material is relatively lower than that of the amine compound, so the lifespan is reduced. Accordingly, there is a need for a method of securing a long life by increasing the stability of a material while maintaining excellent optical properties through the control of the substituent of the boron compound.

본 발명에서는 중수소로 치환된 탄소수 1 내지 3의 알킬기를 포함하는 화합물 및 이를 포함하는 유기 발광 소자를 제공한다. 본 발명 화합물의 C-D 결합은 C-H 결합에 비해 더 강하므로, 화합물의 안정성을 개선시킬 수 있다. 발광성 화합물의 화학적 분해가 상대적으로 약한 C(sp3)-H 결합의 파괴를 수반하는 경우, C-H 결합보다 더 강한 C-D 결합을 이용하여 화합물의 안정성을 더욱 개선할 수 있는 효과가 있다. The present invention provides a compound containing an alkyl group having 1 to 3 carbon atoms substituted with deuterium, and an organic light emitting device including the same. Since the CD bond of the compound of the present invention is stronger than that of the CH bond, the stability of the compound can be improved. When the chemical decomposition of the luminescent compound involves the destruction of the relatively weak C(sp 3 )-H bond, there is an effect of further improving the stability of the compound by using a stronger CD bond than the CH bond.

이때, 전자를 공여해줄 수 있는 치환기로 알킬기를 이용하면 발광특성을 효과적으로 조절하는 것이 가능하지만, 높은 에너지 상태에서 도입된 알킬기가 떨어져나가며 화합물의 분해가 일어나 전체적인 소자의 수명 특성에 문제가 생기게 된다. 탄소수 1 내지 3의 알킬 라디칼인 메틸 라디칼, 에틸 라디칼 및 프로필 라디칼은 (탄소수 4 이상의) 3차 탄소 라디칼에 비해 불안정하므로, C(sp3)-C(sp2)의 결합이 파괴되며 일어나는 화합물의 분해 프로세스가 상대적으로 억제되는 효과가 있다. 따라서, 중수소로 치환된 탄소수 1 내지 3의 알킬기를 사용하는 경우, 청색 소자의 안정성을 확보하면서 발광 특성을 효과적으로 조절하는 것이 가능하다.At this time, if an alkyl group is used as a substituent capable of donating electrons, it is possible to effectively control the luminescence characteristics, but the introduced alkyl group is removed in a high energy state and decomposition of the compound occurs, resulting in a problem in the lifetime characteristics of the overall device. Since the methyl radical, ethyl radical, and propyl radical, which are alkyl radicals having 1 to 3 carbon atoms, are unstable compared to tertiary carbon radicals (more than 4 carbon atoms ), the bond of C(sp 3 )-C(sp 2 ) is destroyed and the resulting compound There is an effect that the decomposition process is relatively suppressed. Therefore, in the case of using an alkyl group having 1 to 3 carbon atoms substituted with deuterium, it is possible to effectively control the light emission characteristics while securing the stability of the blue device.

추가로, 중수소의 더 작은 반데르발스 반경을 이용하면, 기존에 비하여 메틸기, 에틸기 및 프로필기의 입체 장애가 더 작아지므로, 공액을 개선시킬 수 있다.In addition, when a smaller Van der Waals radius of deuterium is used, the steric hindrance of the methyl group, the ethyl group, and the propyl group is smaller than that of the existing one, and conjugation can be improved.

본 명세서에 있어서, "

Figure PCTKR2020012249-appb-I000004
"는 화학식 또는 화합물에 결합되는 위치를 의미한다.In this specification, "
Figure PCTKR2020012249-appb-I000004
"Means a position bonded to a formula or compound.

본 명세서에 있어서, 어떤 부분이 어떤 구성요소를 "포함" 한다고 할 때, 이는 특별히 반대되는 기재가 없는 한 다른 구성요소를 제외하는 것이 아니라 다른 구성 요소를 더 포함할 수 있는 것을 의미한다.In the present specification, when a part "includes" a certain component, it means that other components may be further included rather than excluding other components unless otherwise stated.

본 명세서에 있어서, 어떤 부재가 다른 부재 "상에" 위치하고 있다고 할 때, 이는 어떤 부재가 다른 부재에 접해 있는 경우뿐 아니라 두 부재 사이에 또 다른 부재가 존재하는 경우도 포함한다.In the present specification, when a member is said to be positioned "on" another member, this includes not only the case where the member is in contact with the other member, but also the case where another member exists between the two members.

본 명세서에서 치환기의 예시들은 아래에서 설명하나, 이에 한정되는 것은 아니다.Examples of the substituent in the present specification are described below, but are not limited thereto.

상기 "치환" 이라는 용어는 화합물의 탄소 원자에 결합된 수소 원자가 다른 치환기로 바뀌는 것을 의미하며, 치환되는 위치는 수소 원자가 치환되는 위치 즉, 치환기가 치환 가능한 위치라면 한정하지 않으며, 2 이상 치환되는 경우, 2 이상의 치환기는 서로 동일하거나 상이할 수 있다.The term "substituted" means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, the position where the substituent can be substituted, and when two or more are substituted , Two or more substituents may be the same or different from each other.

본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 니트릴기(-CN); 니트로기; 히드록시기; 알킬기; 시클로알킬기; 알콕시기; 포스핀옥사이드기; 아릴옥시기; 알킬티옥시기; 아릴티옥시기; 알킬티오기; 아릴티오기; 알킬술포닐기; 아릴술포닐기; 알킬술폭시기; 아릴술폭시기; 알케닐기; 실릴기; 붕소기; 아민기; 아릴기; 또는 헤테로고리기로 이루어진 군에서 선택된 1 또는 2 이상의 치환기로 치환되었거나 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환기로 치환되거나, 또는 어떠한 치환기도 갖지 않는 것을 의미한다. 예컨대, "2 이상의 치환기가 연결된 치환기"는 바이페닐기일 수 있다. 즉, 바이페닐기는 아릴기일 수도 있고, 2개의 페닐기가 연결된 치환기로 해석될 수도 있다.In the present specification, the term "substituted or unsubstituted" refers to deuterium; Halogen group; Nitrile group (-CN); Nitro group; Hydroxy group; Alkyl group; Cycloalkyl group; Alkoxy group; Phosphine oxide group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkylthio group; Arylthio group; Alkylsulfonyl group; Arylsulfonyl group; Alkyl sulfoxy group; Arylsulfoxy group; Alkenyl group; Silyl group; Boron group; Amine group; Aryl group; Or it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, or two or more of the substituents exemplified above are substituted with a connected substituent, or does not have any substituents. For example, "a substituent to which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are connected.

본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 알킬기; 시클로알킬기; 알콕시기; 아릴옥시기; 알킬티오기; 아릴티오기; 알킬술포닐기; 아릴술포닐기; 실릴기; 붕소기; 아민기; 아릴기; 또는 헤테로고리기로 이루어진 군에서 선택된 1 또는 2 이상의 치환기로 치환되었거나 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환기로 치환되거나, 또는 어떠한 치환기도 갖지 않는 것을 의미한다.In the present specification, the term "substituted or unsubstituted" refers to deuterium; Halogen group; Alkyl group; Cycloalkyl group; Alkoxy group; Aryloxy group; Alkylthio group; Arylthio group; Alkylsulfonyl group; Arylsulfonyl group; Silyl group; Boron group; Amine group; Aryl group; Or it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, or two or more of the substituents exemplified above are substituted with a connected substituent, or does not have any substituents.

본 명세서에서 "A, B 또는 C로 치환 또는 비치환된" 이라는 용어는 치환기 A 내지 C로 이루어진 군에서 선택된 1 이상의 기 또는 상기 군에서 선택된 2 이상의 기가 연결된 기로 치환 또는 비치환된다는 것을 의미한다. 예컨대, A로 치환 또는 비치환되거나, B로 치환 또는 비치환되거나, C로 치환 또는 비치환되거나, -A-B로 치환 또는 비치환되거나, -B-C로 치환 또는 비치환되거나, -C-A로 치환 또는 비치환되거나, -C-C로 치환 또는 비치환되거나, -A-B-C로 치환 또는 비치환될 수 있거나, -B-C-A로 치환 또는 비치환될 수 있거나, -A-A-B로 치환 또는 비치환될 수 있거나, -A-(C)2로 치환 또는 비치환될 수 있으며, 상기 예시한 바에 한정되지 않는다.In the present specification, the term "substituted or unsubstituted with A, B or C" means that one or more groups selected from the group consisting of substituents A to C or two or more groups selected from the group are substituted or unsubstituted with a linked group. For example, substituted or unsubstituted with A, substituted or unsubstituted with B, substituted or unsubstituted with C, substituted or unsubstituted with -AB, substituted or unsubstituted with -BC, or substituted or unsubstituted with -CA Substituted or unsubstituted with -CC, may be substituted or unsubstituted with -ABC, may be substituted or unsubstituted with -BCA, may be unsubstituted or substituted with -AAB, or -A-(C ) It may be substituted or unsubstituted with 2 , and is not limited to the above exemplified bar.

본 명세서에 있어서, 중수소로 N% 치환되었다는 것은 해당 구조에서 이용가능한 수소의 N%가 중수소로 치환되는 것을 의미한다. 예를 들어, 디벤조퓨란에서 중수소로 25% 치환되었다고 하면, 디벤조퓨란의 8개의 수소 중 2개가 중수소로 치환된 것을 의미한다.In the present specification, N% substitution with deuterium means that N% of the hydrogen available in the structure is substituted with deuterium. For example, supposing that 25% of dibenzofuran is substituted with deuterium, it means that two of the eight hydrogens in dibenzofuran have been substituted with deuterium.

본 명세서에 있어서, 중수소화된 정도는 핵자기 공명 분광법(1H NMR)이나 GC/MS 등의 공지의 방법으로 확인할 수 있다.In the present specification, the degree of deuteration can be confirmed by a known method such as nuclear magnetic resonance spectroscopy (1H NMR) or GC/MS.

상기 치환기들의 예시들은 아래에서 설명하나, 이에 한정되는 것은 아니다. Examples of the substituents are described below, but are not limited thereto.

본 명세서에 있어서, 할로겐기의 예로는 불소(-F), 염소(-Cl), 브롬(-Br) 또는 요오드(-I)가 있다.In the present specification, examples of the halogen group include fluorine (-F), chlorine (-Cl), bromine (-Br), or iodine (-I).

본 명세서에 있어서, 실릴기는 -SiYaYbYc의 화학식으로 표시될 수 있고, 상기 Ya, Yb 및 Yc는 각각 수소; 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기일 수 있다. 상기 실릴기는 구체적으로 트리메틸실릴기, 트리에틸실릴기, t-부틸디메틸실릴기, 비닐디메틸실릴기, 프로필디메틸실릴기, 트리페닐실릴기, 디페닐실릴기, 페닐실릴기 등이 있으나 이에 한정되지 않는다. In the present specification, the silyl group may be represented by the formula of -SiY a Y b Y c , wherein Y a , Y b and Y c are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like, but is not limited thereto. Does not.

본 명세서에 있어서, 붕소기는 -BYdYe의 화학식으로 표시될 수 있고, 상기 Yd 및 Ye는 각각 수소; 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기일 수 있다. 상기 붕소기는 구체적으로 트리메틸붕소기, 트리에틸붕소기, t-부틸디메틸붕소기, 트리페닐붕소기, 페닐붕소기 등이 있으나 이에 한정되지 않는다.In the present specification, the boron group may be represented by the formula of -BY d Y e , wherein Y d and Y e are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The boron group specifically includes a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, and a phenyl boron group, but is not limited thereto.

본 명세서에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 60인 것이 바람직하다. 일 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 30이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 10이다. 알킬기의 구체적인 예로는 메틸기, 에틸기, 프로필기, n-프로필기, 이소프로필기, 부틸기, n-부틸기, 이소부틸기, tert-부틸기, 펜틸기, n-펜틸기, 헥실기, n-헥실기, 헵틸기, n-헵틸기, 옥틸기, n-옥틸기 등이 있으나, 이들에 한정되지 않는다. In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to an exemplary embodiment, the alkyl group has 1 to 30 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, pentyl group, n-pentyl group, hexyl group, n -Hexyl group, heptyl group, n-heptyl group, octyl group, n-octyl group, and the like, but are not limited thereto.

본 명세서에 있어서, 아릴알킬기는 아릴기로 치환된 것을 제외하고는 전술한 알킬기에 관한 설명이 적용될 수 있다.In the present specification, the description of the above alkyl group may be applied except that the arylalkyl group is substituted with an aryl group.

본 명세서에 있어서, 상기 알콕시기는 직쇄, 분지쇄 또는 고리쇄일 수 있다. 알콕시기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 20인 것이 바람직하다. 구체적으로, 메톡시, 에톡시, n-프로폭시, 이소프로폭시, i-프로필옥시, n-부톡시, 이소부톡시, tert-부톡시, sec-부톡시, n-펜틸옥시, 네오펜틸옥시, 이소펜틸옥시, n-헥실옥시, 3,3-디메틸부틸옥시, 2-에틸부틸옥시, n-옥틸옥시, n-노닐옥시, n-데실옥시 등이 될 수 있으나, 이에 한정되는 것은 아니다. In the present specification, the alkoxy group may be a straight chain, branched chain, or cyclic chain. Although the number of carbon atoms of the alkoxy group is not particularly limited, it is preferably 1 to 20 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, etc., but is not limited thereto. .

본 명세서에 기재된 알킬기, 알콕시기 및 그 외 알킬기 부분을 포함하는 치환체는 직쇄 또는 분쇄 형태를 모두 포함한다.Substituents including an alkyl group, an alkoxy group and other alkyl group moieties described in the present specification include all of the straight chain or branched form.

본 명세서에 있어서, 시클로알킬기는 특별히 한정되지 않으나, 탄소수 3 내지 60인 것이 바람직하며, 일 실시상태에 따르면, 상기 시클로알킬기의 탄소수는 3 내지 30이다. 또 하나의 실시상태에 따르면, 상기 시클로알킬기의 탄소수는 3 내지 20이다. 또 하나의 실시상태에 따르면, 상기 시클로알킬기의 탄소수는 3 내지 6이다. 구체적으로 시클로프로필기, 시클로부틸기, 시클로펜틸기, 시클로헥실기, 시클로헵틸기, 시클로옥틸기, 아다만틸기 등이 있으나, 이에 한정되지 않는다.In the present specification, the cycloalkyl group is not particularly limited, but is preferably 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, and the like, but is not limited thereto.

본 명세서에 있어서, 아민기는 -NH2이며, 상기 아민기에는 전술한 알킬기, 아릴기, 헤테로고리기, 알케닐기, 시클로알킬기 및 이들의 조합 등이 치환될 수 있다. 상기 치환된 아민기의 탄소수는 특별히 한정되지 않으나, 1 내지 30인 것이 바람직하다. 일 실시상태에 따르면, 상기 아민기의 탄소수는 1 내지 20이다. 일 실시상태에 따르면, 상기 아민기의 탄소수는 1 내지 10이다. 치환된 아민기의 구체적인 예로는 메틸아민기, 디메틸아민기, 에틸아민기, 디에틸아민기, 페닐아민기, 9,9-디메틸플루오레닐페닐아민기, 피리딜페닐아민기, 디페닐아민기, 페닐피리딜아민기, 나프틸아민기, 바이페닐아민기, 안트라세닐아민기, 디벤조퓨라닐페닐아민기, 9-메틸안트라세닐아민기, 디페닐아민기, 페닐나프틸아민기, 디톨릴아민기, 페닐톨릴아민기, 디페닐아민기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present specification, the amine group is -NH 2 , and the above-described alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, and combinations thereof may be substituted in the amine group. The number of carbon atoms of the substituted amine group is not particularly limited, but is preferably 1 to 30. According to an exemplary embodiment, the amine group has 1 to 20 carbon atoms. According to an exemplary embodiment, the amine group has 1 to 10 carbon atoms. Specific examples of the substituted amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, 9,9-dimethylfluorenylphenylamine group, pyridylphenylamine group, diphenylamine Group, phenylpyridylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, dibenzofuranylphenylamine group, 9-methylanthracenylamine group, diphenylamine group, phenylnaphthylamine group, Although there are a ditolylamine group, a phenyltolylamine group, a diphenylamine group, etc., it is not limited to these.

본 명세서에 있어서, 아릴기는 특별히 한정되지 않으나 탄소수 6 내지 60인 것이 바람직하며, 단환식 아릴기 또는 다환식 아릴기일 수 있다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 30이다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 20이다. 상기 아릴기가 단환식 아릴기로는 페닐기, 바이페닐기, 터페닐기, 쿼터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. 상기 다환식 아릴기로는 나프틸기, 안트라세닐기, 페난트레닐기, 파이레닐기, 페릴레닐기, 트리페닐기, 크라이세닐기, 플루오레닐기, 트리페닐레닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group such as a phenyl group, a biphenyl group, a terphenyl group, or a quarterphenyl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a triphenyl group, a chrysenyl group, a fluorenyl group, a triphenylenyl group, and the like, but is limited thereto. no.

본 명세서에 있어서, 플루오레닐기는 치환될 수 있고, 치환기 2개가 서로 결합하여 스피로 구조를 형성할 수 있다.In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.

상기 플루오레닐기가 치환되는 경우,

Figure PCTKR2020012249-appb-I000005
,
Figure PCTKR2020012249-appb-I000006
등의 스피로플루오레닐기,
Figure PCTKR2020012249-appb-I000007
(9,9-디메틸플루오레닐기), 및
Figure PCTKR2020012249-appb-I000008
(9,9-디페닐플루오레닐기) 등의 치환된 플루오레닐기가 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,
Figure PCTKR2020012249-appb-I000005
,
Figure PCTKR2020012249-appb-I000006
Spirofluorenyl groups such as,
Figure PCTKR2020012249-appb-I000007
(9,9-dimethylfluorenyl group), and
Figure PCTKR2020012249-appb-I000008
It may be a substituted fluorenyl group such as (9,9-diphenylfluorenyl group). However, it is not limited thereto.

본 명세서에 있어서, 아릴옥시기 중의 아릴기는 전술한 아릴기에 관한 설명이 적용될 수 있다.In the present specification, the aryl group in the aryloxy group may be described above with respect to the aryl group.

본 명세서에 있어서, 상기 알킬티오기 및 알킬술포닐기 중의 알킬기에는 전술한 알킬기에 관한 설명이 적용될 수 있다.In the present specification, the above description of the alkyl group may be applied to the alkyl group in the alkylthio group and the alkylsulfonyl group.

본 명세서에 있어서, 상기 아릴티오기 및 아릴술포닐기 중의 아릴기에는 전술한 아릴기에 관한 설명이 적용될 수 있다.In the present specification, the description of the aryl group described above may be applied to the aryl group in the arylthio group and the arylsulfonyl group.

본 명세서에 있어서, 상기 알킬티옥시기 및 알킬술폭시기 중의 알킬기에는 전술한 알킬기에 관한 설명이 적용될 수 있다.In the present specification, the above-described description of the alkyl group may be applied to the alkyl group in the alkyl thioxy group and the alkyl sulfoxy group.

본 명세서에 있어서, 상기 아릴티옥시기 및 아릴술폭시기 중의 아릴기에는 전술한 아릴기에 관한 설명이 적용될 수 있다.In the present specification, the description of the aryl group described above may be applied to the aryl group in the arylthioxy group and the arylsulfoxy group.

본 명세서에 있어서, 헤테로고리기는 이종원자로 N, O, P, S, Si 및 Se 중 1개 이상을 포함하는 고리기로서, 탄소수는 특별히 한정되지 않으나 탄소수 2 내지 60인 것이 바람직하다. 일 실시상태에 따르면, 상기 헤테로고리기의 탄소수는 2 내지 30이다. 헤테로고리기의 예로는 예로는 피리딘기, 피롤기, 피리미딘기, 퀴놀린기, 피리다지닐기, 퓨란기, 티오펜기, 이미다졸기, 피라졸기, 디벤조퓨란기, 디벤조티오펜기, 카바졸기, 벤조카바졸기, 나프토벤조퓨란기, 벤조나프토티오펜기, 인데노카바졸기, 트리아지닐기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present specification, the heterocyclic group is a cyclic group including at least one of N, O, P, S, Si, and Se as hetero atoms, and the number of carbons is not particularly limited, but is preferably 2 to 60 carbon atoms. According to an exemplary embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30. Examples of the heterocyclic group include pyridine group, pyrrole group, pyrimidine group, quinoline group, pyridazinyl group, furan group, thiophene group, imidazole group, pyrazole group, dibenzofuran group, dibenzothiophene group , Carbazole group, benzocarbazole group, naphthobenzofuran group, benzonaphthothiophene group, indenocarbazole group, triazinyl group, and the like, but are not limited thereto.

본 명세서에 있어서, 헤테로아릴기는 방향족인 것을 제외하고는 전술한 헤테로고리기에 관한 설명이 적용될 수 있다.In the present specification, the description of the aforementioned heterocyclic group may be applied except that the heteroaryl group is aromatic.

본 명세서에 있어서, 인접한 기와 서로 결합하여 형성되는 치환 또는 비치환된 고리에서, "고리"는 탄화수소 고리; 또는 헤테로 고리를 의미한다.In the present specification, in a substituted or unsubstituted ring formed by bonding with adjacent groups to each other, "ring" is a hydrocarbon ring; Or a hetero ring.

상기 탄화수소 고리는 방향족, 지방족 또는 방향족과 지방족의 축합고리일 수 있으며, 1가기인 것을 제외하고는 상기 시클로알킬기 또는 아릴기의 예시 중에서 선택될 수 있다.The hydrocarbon ring may be an aromatic, aliphatic, or condensed ring of aromatic and aliphatic, and may be selected from examples of the cycloalkyl group or an aryl group, except that it is a monovalent group.

본 명세서에 있어서, 인접하는 기와 서로 결합하여 고리를 형성한다는 의미는 인접하는 기와 서로 결합하여 치환 또는 비치환된 지방족 탄화수소고리; 치환 또는 비치환된 방향족 탄화수소고리; 치환 또는 비치환된 지방족 헤테로고리; 치환 또는 비치환된 방향족 헤테로고리; 또는 이들의 축합고리를 형성하는 것을 의미한다. 상기 탄화수소고리는 탄소와 수소 원자로만 이루어진 고리를 의미한다. 상기 헤테로고리는 N, O, P, S, Si 및 Se 중에서 선택된 1 이상으로 포함하는 고리를 의미한다. 본 명세서에 있어서, 상기 지방족 탄화수소고리, 방향족 탄화수소고리, 지방족 헤테로고리 및 방향족 헤테로고리는 단환 또는 다환일 수 있다.In the present specification, the meaning of forming a ring by bonding with adjacent groups to each other means a substituted or unsubstituted aliphatic hydrocarbon ring by bonding with adjacent groups; A substituted or unsubstituted aromatic hydrocarbon ring; Substituted or unsubstituted aliphatic heterocycle; Substituted or unsubstituted aromatic heterocycle; Or it means to form a condensed ring of these. The hydrocarbon ring means a ring consisting only of carbon and hydrogen atoms. The heterocycle refers to a ring including at least one selected from N, O, P, S, Si and Se. In the present specification, the aliphatic hydrocarbon ring, the aromatic hydrocarbon ring, the aliphatic hetero ring and the aromatic hetero ring may be monocyclic or polycyclic.

본 명세서에 있어서, 지방족 탄화수소고리란 방향족이 아닌 고리로서 탄소와 수소 원자로만 이루어진 고리를 의미한다. 지방족 탄화수소고리의 예로는 시클로프로판, 시클로부탄, 시클로부텐, 시클로펜탄, 시클로펜텐, 시클로헥산, 시클로헥센, 1,4-시클로헥사디엔, 시클로헵탄, 시클로헵텐, 시클로옥탄, 시클로옥텐 등이 있으나, 이에 한정되지 않는다.In the present specification, the aliphatic hydrocarbon ring refers to a ring that is not aromatic and includes only carbon and hydrogen atoms. Examples of aliphatic hydrocarbon rings include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, and the like, It is not limited to this.

본 명세서에 있어서, 방향족 탄화수소고리란 탄소와 수소 원자로만 이루어진 방향족의 고리를 의미한다. 방향족 탄화수소고리의 예로는 벤젠, 나프탈렌, 안트라센, 페난트렌, 페릴렌, 플루오란텐, 트리페닐렌, 페날렌, 파이렌, 테트라센, 크라이센, 펜타센, 플루오렌, 인덴, 아세나프틸렌, 벤조플루오렌, 스피로플루오렌 등이 있으나, 이에 한정되지 않는다. 본 명세서에 있어서, 방향족 탄화수소고리는 아릴기와 동일한 의미로 해석될 수 있다.In the present specification, the aromatic hydrocarbon ring means an aromatic ring consisting only of carbon and hydrogen atoms. Examples of aromatic hydrocarbon rings include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenalene, pyrene, tetracene, chrysene, pentacene, fluorene, indene, acenaphthylene, Benzofluorene, spirofluorene, and the like, but are not limited thereto. In the present specification, the aromatic hydrocarbon ring may be interpreted as having the same meaning as an aryl group.

본 명세서에 있어서, 지방족 헤테로고리란 헤테로원자 중 1개 이상을 포함하는 지방족 고리를 의미한다. 지방족 헤테로고리의 예로는, 옥시레인(oxirane), 테트라하이드로퓨란, 1,4-디옥세인(1,4-dioxane), 피롤리딘, 피페리딘, 모르폴린(morpholine), 옥세판, 아조케인, 티오케인 등이 있으나, 이에 한정되지 않는다.In the present specification, the aliphatic heterocycle means an aliphatic ring containing one or more of heteroatoms. Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxephan, and azocaine , Thiocane, and the like, but are not limited thereto.

본 명세서에 있어서, 방향족 헤테로고리란 헤테로원자 중 1개 이상을 포함하는 방향족 고리를 의미한다. 방향족 헤테로고리의 예로는, 피리딘, 피롤, 피리미딘, 피리다진, 퓨란, 티오펜, 이미다졸, 파라졸, 옥사졸, 이소옥사졸, 티아졸, 이소티아졸, 트리아졸, 옥사디아졸, 티아디아졸, 디티아졸, 테트라졸, 피란, 티오피란, 디아진, 옥사진, 티아진, 다이옥신, 트리아진, 테트라진, 이소퀴놀린, 퀴놀린, 퀴논, 퀴나졸린, 퀴녹살린, 나프티리딘, 아크리딘, 페난트리딘, 디아자나프탈렌, 드리아자인덴, 인돌, 인돌리진, 벤조티아졸, 벤조옥사졸, 벤조이미다졸, 벤조티오펜, 벤조퓨란, 디벤조티오펜, 디벤조퓨란, 카바졸, 벤조카바졸, 디벤조카바졸, 페나진, 이미다조피리딘, 페녹사진, 인돌로카바졸, 인데노카바졸 등이 있으나, 이에 한정되지 않는다.In the present specification, the aromatic heterocycle means an aromatic ring containing at least one heteroatom. Examples of aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, parasol, oxazole, isoxazole, thiazole, isothiazole, triazole, oxadiazole, thia Diazole, dithiazole, tetrazole, pyran, thiopyran, diazine, oxazine, thiazine, dioxin, triazine, tetrazine, isoquinoline, quinoline, quinone, quinazoline, quinoxaline, naphthyridine, acridine , Phenanthridine, diazanaphthalene, dryazainden, indole, indolizine, benzothiazole, benzoxazole, benzoimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzo Carbazole, dibenzocarbazole, phenazine, imidazopyridine, phenoxazine, indolocarbazole, indenocarbazole, and the like, but are not limited thereto.

이하 본 발명의 바람직한 실시상태를 상세히 설명한다. 그러나 본 발명의 실시상태는 여러 가지 형태로 변형될 수 있으며, 본 발명의 범위가 아래에서 설명하는 실시상태들에 한정되지는 않는다.Hereinafter, a preferred embodiment of the present invention will be described in detail. However, the exemplary embodiment of the present invention may be modified in various forms, and the scope of the present invention is not limited to the exemplary embodiments described below.

이하 본 발명의 바람직한 실시상태를 상세히 설명한다. 그러나 본 발명의 실시상태는 여러 가지 형태로 변형될 수 있으며, 본 발명의 범위가 아래에서 설명하는 실시상태들에 한정되지는 않는다.Hereinafter, a preferred embodiment of the present invention will be described in detail. However, the exemplary embodiment of the present invention may be modified in various forms, and the scope of the present invention is not limited to the exemplary embodiments described below.

본 명세서는 하기 화학식 1로 표시되는 화합물을 제공한다. 하기 화학식 1로 표시되는 화합물을 유기 발광 소자의 유기물층에 사용하는 경우, 유기 발광 소자의 효율이 향상될 뿐만 아니라, 낮은 구동전압을 가지고, 우수한 수명특성을 갖는다.The present specification provides a compound represented by the following formula (1). When the compound represented by the following formula (1) is used in the organic material layer of the organic light-emitting device, the efficiency of the organic light-emitting device is improved, as well as a low driving voltage and excellent lifespan characteristics.

[화학식 1][Formula 1]

Figure PCTKR2020012249-appb-I000009
Figure PCTKR2020012249-appb-I000009

상기 화학식 1에 있어서, In Formula 1,

A1 및 A2는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 지방족 탄화수소고리; 치환 또는 비치환된 방향족 탄화수소고리; 치환 또는 비치환된 방향족 헤테로고리; 또는 치환 또는 비치환된 지방족 탄화수소고리 및 방향족 탄화수소고리의 축합고리이고,A1 and A2 are the same as or different from each other, and each independently a substituted or unsubstituted aliphatic hydrocarbon ring; A substituted or unsubstituted aromatic hydrocarbon ring; Substituted or unsubstituted aromatic heterocycle; Or a condensed ring of a substituted or unsubstituted aliphatic hydrocarbon ring and an aromatic hydrocarbon ring,

X1 및 X2는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 또는 치환 또는 비치환된 알킬기이거나, -CRaRb-, -NRc-, -O-, -PRd-, -S-, -PORe-, -SO2-, -SiRfRg-, 또는 -BRh-를 통해 직접 연결되고, X1 and X2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group, or directly linked through -CRaRb-, -NRc-, -O-, -PRd-, -S-, -PORe-, -SO 2 -, -SiRfRg-, or -BRh- Become,

Ra 내지 Rh는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 알키닐기; 치환 또는 비치환된 아릴알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 인접하는 기는 서로 결합하여 치환 또는 비치환된 고리를 형성하고,Ra To Rh are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,

R1 내지 R5는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아릴티옥시기; 치환 또는 비치환된 알킬티오기; 치환 또는 비치환된 아릴티오기; 치환 또는 비치환된 알킬술포닐기; 치환 또는 비치환된 아릴술포닐기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 알키닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 아릴알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 인접하는 기는 서로 결합하여 치환 또는 비치환된 고리를 형성하고,R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkyl thioxy group; A substituted or unsubstituted arylthioxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfonyl group; A substituted or unsubstituted arylsulfonyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,

Y는 중수소로 치환된 탄소수 1 내지 3의 알킬기; 또는 하기 화학식 2로 표시되고,Y is an alkyl group having 1 to 3 carbon atoms substituted with deuterium; Or represented by the following formula (2),

[화학식 2][Formula 2]

Figure PCTKR2020012249-appb-I000010
Figure PCTKR2020012249-appb-I000010

상기 화학식 2에 있어서,In Formula 2,

B1 및 B2는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 지방족 탄화수소 고리; 또는 치환 또는 비치환된 방향족 탄화수소 고리이고,B1 and B2 are the same as or different from each other, and each independently a substituted or unsubstituted aliphatic hydrocarbon ring; Or a substituted or unsubstituted aromatic hydrocarbon ring,

R6 및 R7은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 알키닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 아릴알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 인접하는 기는 서로 결합하여 치환 또는 비치환된 고리를 형성하고,R6 and R7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkyl thioxy group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,

r1 및 r2는 서로 동일하거나 상이하고, 각각 독립적으로 1 내지 3의 정수이고,r1 and r2 are the same as or different from each other, and each independently an integer of 1 to 3,

r3 및 r5 내지 r7는 서로 동일하거나 상이하고, 각각 독립적으로 1 내지 11의 정수이고,r3 and r5 to r7 are the same as or different from each other, and each independently an integer of 1 to 11,

r4는 1 또는 2의 정수이고,r4 is an integer of 1 or 2,

n은 1 또는 2의 정수이고,n is an integer of 1 or 2,

r4+n는 2 또는 3의 정수이고,r4+n is an integer of 2 or 3,

r1 내지 r7 및 n이 각각 2 이상인 경우, 각각의 괄호 안의 치환기는 서로 동일하거나 상이하고,When r1 to r7 and n are each 2 or more, the substituents in each parenthesis are the same as or different from each other,

Y가 중수소로 치환된 탄소수 1 내지 3의 알킬기인 경우, X1, X2 및 R1 내지 R5 중 적어도 하나는 중수소로 치환된 탄소수 1 내지 3의 알킬기이고,When Y is an alkyl group having 1 to 3 carbon atoms substituted with deuterium, at least one of X1, X2 and R1 to R5 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium,

Y가 상기 화학식 2로 표시되는 경우, X1, X2 및 R1 내지 R7 중 적어도 하나는 중수소로 치환된 탄소수 1 내지 3의 알킬기이고,When Y is represented by Formula 2, at least one of X1, X2 and R1 to R7 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium,

Figure PCTKR2020012249-appb-I000011
는 화학식 1에 결합되는 위치를 의미한다.
Figure PCTKR2020012249-appb-I000011
Means a position bonded to the formula (1).

본 명세서의 일 실시상태에 있어서, 상기 화학식 1로 표시되는 화합물의 반치폭은 17 nm 내지 35 nm이다.In the exemplary embodiment of the present specification, the half width of the compound represented by Formula 1 is 17 nm to 35 nm.

본 명세서의 일 실시상태에 있어서, 중수소로 치환된 탄소수 1 내지 3의 알킬기는 -CDH2; -CD2H; -CD3; -C2D5; -CH2CD3; -CD(CD3)2; 또는 -CH(CD3)2로 표시될 수 있다.In an exemplary embodiment of the present specification, the alkyl group having 1 to 3 carbon atoms substituted with deuterium is -CDH 2 ; -CD 2 H; -CD 3 ; -C 2 D 5 ; -CH 2 CD 3 ; -CD(CD 3 ) 2 ; Alternatively, it may be represented by -CH(CD 3 ) 2.

본 명세서의 일 실시상태에 따르면, 중수소로 치환된 메틸기는 -CD3로 표시될 수 있다.According to an exemplary embodiment of the present specification, a methyl group substituted with deuterium may be represented by -CD 3.

본 명세서의 일 실시상태에 따르면, 중수소로 치환된 에틸기는 -C2D5(-CD2CD3) 또는 CH2CD3로 표시될 수 있다.According to an exemplary embodiment of the present specification, the ethyl group substituted with deuterium may be represented by -C 2 D 5 (-CD 2 CD 3 ) or CH 2 CD 3.

본 명세서의 일 실시상태에 따르면, 중수소로 치환된 프로필기는

Figure PCTKR2020012249-appb-I000012
(-CD(CD3)2) 또는
Figure PCTKR2020012249-appb-I000013
(CH(CD3)2)로 표시될 수 있다.
Figure PCTKR2020012249-appb-I000014
는 결합 위치를 의미한다.According to an exemplary embodiment of the present specification, the propyl group substituted with deuterium
Figure PCTKR2020012249-appb-I000012
(-CD(CD 3 ) 2 ) or
Figure PCTKR2020012249-appb-I000013
It can be expressed as (CH(CD 3 ) 2 ).
Figure PCTKR2020012249-appb-I000014
Means the bonding position.

본 명세서의 일 실시상태에 따르면, A1 및 A2는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 단환 내지 4환의 지방족 탄화수소고리; 치환 또는 비치환된 단환 내지 4환의 방향족 탄화수소고리; 치환 또는 비치환된 단환 내지 4환의 방향족 헤테로고리; 또는 치환 또는 비치환된 단환 내지 4환의 지방족 탄화수소고리 및 단환 내지 4환의 방향족 탄화수소고리의 축합고리이다.According to an exemplary embodiment of the present specification, A1 and A2 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic to tetracyclic aliphatic hydrocarbon ring; Substituted or unsubstituted mono- to 4-cyclic aromatic hydrocarbon rings; A substituted or unsubstituted monocyclic to 4 ring aromatic heterocycle; Or a substituted or unsubstituted monocyclic to 4 ring aliphatic hydrocarbon ring and a monocyclic to 4 ring condensed ring of aromatic hydrocarbon ring.

본 명세서의 일 실시상태에 따르면, A1 및 A2는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 단환의 지방족 탄화수소고리; 치환 또는 비치환된 단환 내지 4환의 방향족 탄화수소고리; 치환 또는 비치환된 단환 내지 3환의 방향족 헤테로고리; 또는 치환 또는 비치환된 단환 또는 2환의 지방족 탄화수소고리 및 단환 또는 2환의 방향족 탄화수소고리의 축합고리이다.According to an exemplary embodiment of the present specification, A1 and A2 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic aliphatic hydrocarbon ring; Substituted or unsubstituted mono- to 4-cyclic aromatic hydrocarbon rings; A substituted or unsubstituted monocyclic to tricyclic aromatic heterocycle; Or a substituted or unsubstituted monocyclic or bicyclic aliphatic hydrocarbon ring and a condensed ring of a monocyclic or bicyclic aromatic hydrocarbon ring.

본 명세서의 일 실시상태에 따르면, A1 및 A2는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 3 내지 30의 지방족 탄화수소고리; 치환 또는 비치환된 탄소수 6 내지 30의 방향족 탄화수소고리; 치환 또는 비치환된 탄소수 2 내지 30의 방향족 헤테로고리; 또는 치환 또는 비치환된 탄소수 3 내지 30의 지방족 탄화수소고리 및 탄소수 6 내지 30의 방향족 탄화수소고리의 축합고리이다.According to an exemplary embodiment of the present specification, A1 and A2 are the same as or different from each other, and each independently a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms; A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms; A substituted or unsubstituted C2 to C30 aromatic heterocycle; Or a condensed ring of a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms and an aromatic hydrocarbon ring having 6 to 30 carbon atoms.

본 명세서의 일 실시상태에 따르면, A1 및 A2는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 3 내지 20의 지방족 탄화수소고리; 치환 또는 비치환된 탄소수 6 내지 20의 방향족 탄화수소고리; 치환 또는 비치환된 탄소수 2 내지 20의 방향족 헤테로고리; 또는 치환 또는 비치환된 탄소수 3 내지 20의 지방족 탄화수소고리 및 탄소수 6 내지 20의 방향족 탄화수소고리의 축합고리이다.According to an exemplary embodiment of the present specification, A1 and A2 are the same as or different from each other, and each independently a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 carbon atoms; A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 20 carbon atoms; A substituted or unsubstituted C2 to C20 aromatic heterocycle; Or a condensed ring of a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 carbon atoms and an aromatic hydrocarbon ring having 6 to 20 carbon atoms.

본 명세서의 일 실시상태에 따르면, A1 및 A2는 서로 동일하거나 상이하고, 각각 독립적으로 페닐기 또는 나프틸기로 치환 또는 비치환된 벤젠고리; 치환 또는 비치환된 플루오렌 고리; 치환 또는 비치환된 트리페닐렌 고리; 치환 또는 비치환된 시클로헥산 고리; 치환 또는 비치환된 시클로펜텐 또는 치환 또는 비치환된 시클로헥센이 축합된 치환 또는 비치환된 벤젠고리; 또는 치환 또는 비치환된 디벤조퓨란 고리이다.According to an exemplary embodiment of the present specification, A1 and A2 are the same as or different from each other, and each independently a benzene ring unsubstituted or substituted with a phenyl group or a naphthyl group; A substituted or unsubstituted fluorene ring; A substituted or unsubstituted triphenylene ring; A substituted or unsubstituted cyclohexane ring; A substituted or unsubstituted benzene ring condensed with a substituted or unsubstituted cyclopentene or a substituted or unsubstituted cyclohexene; Or a substituted or unsubstituted dibenzofuran ring.

본 명세서의 일 실시상태에 따르면, A1 및 A2는 서로 동일하거나 상이하고, 각각 독립적으로 하기 화학식 A100 내지 A103 중 어느 하나로 표시된다.According to an exemplary embodiment of the present specification, A1 and A2 are the same as or different from each other, and each independently is represented by any one of the following Chemical Formulas A100 to A103.

[화학식 A100]　　　　　　[화학식 A101][Formula A100]　　　　　　[Formula A101]

Figure PCTKR2020012249-appb-I000015
Figure PCTKR2020012249-appb-I000015

[화학식 A102]　　　　　　[화학식 A103][Formula A102]　　　　　　[Formula A103]

Figure PCTKR2020012249-appb-I000016
Figure PCTKR2020012249-appb-I000016

상기 화학식 A100 내지 A103에 있어서,In the above formulas A100 to A103,

G1은 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성하고,G1 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combined with an adjacent group to form a substituted or unsubstituted ring,

X11은 O; S; 또는 CR101R102이고,X11 is O; S; Or CR101R102,

R101 및 R102는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기이고,R101 and R102 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,

g1은 0 내지 5의 정수이고, g1'은 0 내지 11의 정수이고, g1''은 0 내지 7의 정수이고, g1'''은 0 내지 11의 정수이고,g1 is an integer from 0 to 5, g1' is an integer from 0 to 11, g1'' is an integer from 0 to 7, and g1''' is an integer from 0 to 11,

a1은 1 내지 2의 정수이고,a1 is an integer of 1 to 2,

g1, g1', g1'' 및 g1'''이 각각 2 이상인 경우, 2 이상의 G1은 서로 동일하거나 상이하고,When g1, g1', g1'' and g1''' are each 2 or more, 2 or more G1s are the same as or different from each other,

Figure PCTKR2020012249-appb-I000017
는 화학식 1에 결합되는 위치를 의미한다.
Figure PCTKR2020012249-appb-I000017
Means a position bonded to the formula (1).

본 명세서의 일 실시상태에 따르면, G1은 수소; 중수소; 또는 치환 또는 비치환된 알킬기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성한다.According to an exemplary embodiment of the present specification, G1 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group, or combine with an adjacent group to form a substituted or unsubstituted ring.

본 명세서의 일 실시상태에 따르면, G1은 수소; 중수소; 또는 중수소로 치환 또는 비치환된 탄소수 1 내지 30의 알킬기이거나, 인접한 기와 서로 결합하여 탄소수 6 내지 30의 방향족 탄화수소고리를 형성하거나, R1 또는 R2와 직접결합하여 카바졸 고리; 헥사하이드로카바졸 고리; 또는

Figure PCTKR2020012249-appb-I000018
고리를 이룬다.According to an exemplary embodiment of the present specification, G1 is hydrogen; heavy hydrogen; Or an alkyl group having 1 to 30 carbon atoms substituted or unsubstituted with deuterium, or combined with an adjacent group to form an aromatic hydrocarbon ring having 6 to 30 carbon atoms, or directly bonded to R1 or R2 to form a carbazole ring; Hexahydrocarbazole ring; or
Figure PCTKR2020012249-appb-I000018
Form a loop.

본 명세서의 일 실시상태에 따르면, G1은 수소; 중수소; 또는 중수소로 치환 또는 비치환된 탄소수 1 내지 20의 알킬기이거나, 인접한 기와 서로 결합하여 탄소수 6 내지 20의 방향족 탄화수소고리를 형성하거나, R1 또는 R2와 직접결합하여 카바졸 고리; 헥사하이드로카바졸 고리; 또는

Figure PCTKR2020012249-appb-I000019
고리를 이룬다.According to an exemplary embodiment of the present specification, G1 is hydrogen; heavy hydrogen; Or an alkyl group having 1 to 20 carbon atoms substituted or unsubstituted with deuterium, or combined with an adjacent group to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms, or directly bonded to R1 or R2 to form a carbazole ring; Hexahydrocarbazole ring; or
Figure PCTKR2020012249-appb-I000019
Form a loop.

본 명세서의 일 실시상태에 따르면, G1은 수소; 중수소; 또는 중수소로 치환 또는 비치환된 탄소수 1 내지 10의 알킬기이거나, 인접한 기와 서로 결합하여 벤젠고리; 또는 페난트렌고리를 형성하거나, R1 또는 R2와 직접결합하여 카바졸 고리; 헥사하이드로카바졸 고리; 또는

Figure PCTKR2020012249-appb-I000020
고리를 이룬다.According to an exemplary embodiment of the present specification, G1 is hydrogen; heavy hydrogen; Or an alkyl group having 1 to 10 carbon atoms substituted or unsubstituted with deuterium, or a benzene ring combined with an adjacent group; Or a phenanthrene ring or a carbazole ring by direct bonding with R1 or R2; Hexahydrocarbazole ring; or
Figure PCTKR2020012249-appb-I000020
Form a loop.

본 명세서의 일 실시상태에 따르면, G1은 수소; 중수소; 또는 중수소로 치환 또는 비치환된 탄소수 1 내지 4의 알킬기이거나, 인접한 기와 서로 결합하여 벤젠고리; 또는 페난트렌고리를 형성하거나, R1 또는 R2와 직접결합하여 카바졸 고리; 헥사하이드로카바졸 고리; 또는

Figure PCTKR2020012249-appb-I000021
고리를 이룬다.According to an exemplary embodiment of the present specification, G1 is hydrogen; heavy hydrogen; Or an alkyl group having 1 to 4 carbon atoms substituted or unsubstituted with deuterium, or a benzene ring by bonding with an adjacent group; Or a phenanthrene ring or a carbazole ring by direct bonding with R1 or R2; Hexahydrocarbazole ring; or
Figure PCTKR2020012249-appb-I000021
Form a loop.

본 명세서의 일 실시상태에 따르면, G1은 수소; 중수소; 또는 중수소로 치환 또는 비치환된 메틸기; 중수소로 치환 또는 비치환된 에틸기; 중수소로 치환 또는 비치환된 프로필기; 또는 중수소로 치환 또는 비치환된 부틸기이거나, 인접한 기와 서로 결합하여 페난트렌고리를 형성하거나, R1 또는 R2와 직접결합하여 카바졸 고리; 헥사하이드로카바졸 고리; 또는

Figure PCTKR2020012249-appb-I000022
고리를 이룬다.According to an exemplary embodiment of the present specification, G1 is hydrogen; heavy hydrogen; Or a methyl group unsubstituted or substituted with deuterium; An ethyl group unsubstituted or substituted with deuterium; A propyl group unsubstituted or substituted with deuterium; Or a butyl group substituted or unsubstituted with deuterium, or a phenanthrene ring by bonding with an adjacent group to form a phenanthrene ring, or a carbazole ring by directly bonding with R1 or R2; Hexahydrocarbazole ring; or
Figure PCTKR2020012249-appb-I000022
Form a loop.

본 명세서의 일 실시상태에 따르면, G1은 수소; 중수소; 또는 중수소로 치환 또는 비치환된 메틸기; 중수소로 치환 또는 비치환된 에틸기; 중수소로 치환 또는 비치환된 i-프로필기; 또는 중수소로 치환 또는 비치환된 t-부틸기이거나, 인접한 기와 서로 결합하여 페난트렌고리를 형성하거나, R1 또는 R2와 직접결합하여 카바졸 고리; 헥사하이드로카바졸 고리; 또는

Figure PCTKR2020012249-appb-I000023
고리를 이룬다.According to an exemplary embodiment of the present specification, G1 is hydrogen; heavy hydrogen; Or a methyl group unsubstituted or substituted with deuterium; An ethyl group unsubstituted or substituted with deuterium; I-propyl group unsubstituted or substituted with deuterium; Or a t-butyl group substituted or unsubstituted with deuterium, or bonded to an adjacent group to form a phenanthrene ring, or directly bonded to R1 or R2 to form a carbazole ring; Hexahydrocarbazole ring; or
Figure PCTKR2020012249-appb-I000023
Form a loop.

본 명세서의 일 실시상태에 따르면, X11은 O; 또는 CR101R102이다.According to an exemplary embodiment of the present specification, X11 is O; Or CR101R102.

본 명세서의 일 실시상태에 따르면, R101 및 R102는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기이다.According to an exemplary embodiment of the present specification, R101 and R102 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

본 명세서의 일 실시상태에 따르면, R101 및 R102는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 1 내지 30의 알킬기; 또는 치환 또는 비치환된 탄소수 6 내지 30의 아릴기이다.According to an exemplary embodiment of the present specification, R101 and R102 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

본 명세서의 일 실시상태에 따르면, R101 및 R102는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 1 내지 20의 알킬기; 또는 치환 또는 비치환된 탄소수 6 내지 20의 아릴기이다.According to an exemplary embodiment of the present specification, R101 and R102 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

본 명세서의 일 실시상태에 따르면, R101 및 R102는 서로 동일하거나 상이하고, 각각 독립적으로 중수소로 치환 또는 비치환된 알킬기; 또는 중수소로 치환 또는 비치환된 아릴기이다.According to an exemplary embodiment of the present specification, R101 and R102 are the same as or different from each other, and each independently an alkyl group unsubstituted or substituted with deuterium; Or an aryl group unsubstituted or substituted with deuterium.

본 명세서의 일 실시상태에 따르면, R101 및 R102는 서로 동일하거나 상이하고, 각각 독립적으로 중수소로 치환 또는 비치환된 메틸기; 또는 페닐기이다.According to an exemplary embodiment of the present specification, R101 and R102 are the same as or different from each other, and each independently a methyl group unsubstituted or substituted with deuterium; Or a phenyl group.

본 명세서의 일 실시상태에 따르면, R101 및 R102는 중수소로 치환 또는 비치환된 메틸기이다.According to an exemplary embodiment of the present specification, R101 and R102 are methyl groups unsubstituted or substituted with deuterium.

본 명세서의 일 실시상태에 따르면, R101 및 R102는 메틸기; 또는 CD3이다.According to an exemplary embodiment of the present specification, R101 and R102 is a methyl group; Or CD 3 .

본 명세서의 일 실시상태에 따르면, a1은 1 또는 2이다.According to an exemplary embodiment of the present specification, a1 is 1 or 2.

본 명세서의 일 실시상태에 따르면, g1은 1 내지 4이다.According to an exemplary embodiment of the present specification, g1 is 1 to 4.

본 명세서의 일 실시상태에 따르면, g1'은 1 내지 4이다.According to an exemplary embodiment of the present specification, g1' is 1 to 4.

본 명세서의 일 실시상태에 따르면, g1''은 1 내지 4이다.According to an exemplary embodiment of the present specification, g1'' is 1 to 4.

본 명세서의 일 실시상태에 따르면, g1'''은 1 내지 4이다.According to an exemplary embodiment of the present specification, g1"' is 1 to 4.

본 명세서의 일 실시상태에 따르면, A1 및 A2는 서로 동일하거나 상이하고, 각각 독립적으로 하기 구조들 중 어느 하나로 표시된다.According to an exemplary embodiment of the present specification, A1 and A2 are the same as or different from each other, and are each independently represented by any one of the following structures.

Figure PCTKR2020012249-appb-I000024
Figure PCTKR2020012249-appb-I000024

상기 구조들에 있어서,In the above structures,

R101 내지 R103, G101 및 G102은 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기이고,R101 to R103, G101 and G102 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,

Figure PCTKR2020012249-appb-I000025
는 화학식 1에 결합되는 위치를 의미하고,
Figure PCTKR2020012249-appb-I000025
Means a position bonded to Formula 1,

*는 R1 또는 R2와 결합하는 위치를 의미한다.* Means a position bonded to R1 or R2.

본 명세서의 일 실시상태에 따르면, R103은 치환 또는 비치환된 아릴기이다.According to an exemplary embodiment of the present specification, R103 is a substituted or unsubstituted aryl group.

본 명세서의 일 실시상태에 따르면, R103은 치환 또는 비치환된 탄소수 6 내지 30의 아릴기이다.According to an exemplary embodiment of the present specification, R103 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

본 명세서의 일 실시상태에 따르면, R103은 치환 또는 비치환된 탄소수 6 내지 20의 아릴기이다.According to an exemplary embodiment of the present specification, R103 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

본 명세서의 일 실시상태에 따르면, R103은 중수소, 메틸기 또는 CD3로 치환 또는 비치환된 아릴기이다.According to an exemplary embodiment of the present specification, R103 is an aryl group unsubstituted or substituted with deuterium, a methyl group, or CD 3.

본 명세서의 일 실시상태에 따르면, R103은 중수소, 메틸기 또는 CD3로 치환 또는 비치환된 페닐기이다.According to an exemplary embodiment of the present specification, R103 is a phenyl group unsubstituted or substituted with deuterium, a methyl group, or CD 3.

본 명세서의 일 실시상태에 따르면, R103은 CD3로 치환 또는 비치환된 페닐기이다.According to an exemplary embodiment of the present specification, R103 is a phenyl group unsubstituted or substituted with CD 3.

본 명세서의 일 실시상태에 따르면, G101 및 G102는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 알킬기이다.According to an exemplary embodiment of the present specification, G101 and G102 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group.

본 명세서의 일 실시상태에 따르면, G101 및 G102는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 1 내지 30의 알킬기이다.According to an exemplary embodiment of the present specification, G101 and G102 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

본 명세서의 일 실시상태에 따르면, G101 및 G102는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 1 내지 20의 알킬기이다.According to an exemplary embodiment of the present specification, G101 and G102 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

본 명세서의 일 실시상태에 따르면, G101 및 G102는 서로 동일하거나 상이하고, 각각 독립적으로 중수소로 치환 또는 비치환된 알킬기이다.According to an exemplary embodiment of the present specification, G101 and G102 are the same as or different from each other, and each independently a deuterium-substituted or unsubstituted alkyl group.

본 명세서의 일 실시상태에 따르면, G101 및 G102는 메틸기; 또는 CD3이다.According to an exemplary embodiment of the present specification, G101 and G102 are methyl groups; Or CD 3 .

본 명세서의 일 실시상태에 따르면, A1 및 A2는 서로 동일하거나 상이하고, 각각 독립적으로 벤젠고리; 트리페닐렌고리; 플루오렌고리; 시클로헥산고리; 디벤조퓨란고리; 시클로펜텐이 축합된 벤젠고리; 또는 시클로헥산이 축합된 벤젠고리이고, 상기 치환기들은 G1으로 치환 또는 비치환된다.According to an exemplary embodiment of the present specification, A1 and A2 are the same as or different from each other, and each independently a benzene ring; Triphenylene ring; Fluorene ring; Cyclohexane ring; Dibenzofuran ring; Benzene ring condensed with cyclopentene; Or a benzene ring condensed with cyclohexane, and the substituents are unsubstituted or substituted with G1.

본 명세서의 일 실시상태에 따르면, A1 및 A2는 서로 동일하거나 상이하고, 각각 독립적으로 하기 구조들 중 어느 하나로 표시된다.According to an exemplary embodiment of the present specification, A1 and A2 are the same as or different from each other, and are each independently represented by any one of the following structures.

Figure PCTKR2020012249-appb-I000026
Figure PCTKR2020012249-appb-I000026

상기 기들은 중수소; 또는 탄소수 1 내지 3의 알킬기로 치환 또는 비치환된다.The groups are deuterium; Or it is unsubstituted or substituted with an alkyl group having 1 to 3 carbon atoms.

본 명세서의 일 실시상태에 따르면, X1 및 X2는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 또는 치환 또는 비치환된 알킬기이거나, -CRaRb-, -NRc-, -O-, -PRd-, -S-, -PORe-, -SO2-, -SiRfRg-, 또는 -BRh-를 통해 직접 연결된다.According to an exemplary embodiment of the present specification, X1 and X2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group, or directly linked through -CRaRb-, -NRc-, -O-, -PRd-, -S-, -PORe-, -SO 2 -, -SiRfRg-, or -BRh- do.

본 명세서의 일 실시상태에 따르면, X1 및 X2는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 또는 치환 또는 비치환된 탄소수 1 내지 20의 알킬기이거나, -CRaRb-, -NRc-, -O-, -PRd-, -S-, -PORe-, -SO2-, -SiRfRg-, 또는 -BRh-를 통해 직접 연결된다.According to an exemplary embodiment of the present specification, X1 and X2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted C1-C20 alkyl group, -CRaRb-, -NRc-, -O-, -PRd-, -S-, -PORe-, -SO 2 -, -SiRfRg-, or -BRh It is connected directly through -.

본 명세서의 일 실시상태에 따르면, X1 및 X2는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 또는 치환 또는 비치환된 탄소수 1 내지 10의 알킬기이거나, -CRaRb-, -NRc-, -O-, -PRd-, -S-, -PORe-, -SO2-, -SiRfRg-, 또는 -BRh-를 통해 직접 연결된다.According to an exemplary embodiment of the present specification, X1 and X2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, -CRaRb-, -NRc-, -O-, -PRd-, -S-, -PORe-, -SO 2 -, -SiRfRg-, or -BRh It is connected directly through -.

본 명세서의 일 실시상태에 따르면, X1 및 X2는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 또는 중수소로 치환 또는 비치환된 알킬기이거나, -CRaRb-, -NRc-, -O-, -PRd-, -S-, -PORe-, -SO2-, -SiRfRg-, 또는 -BRh-를 통해 직접 연결된다.According to an exemplary embodiment of the present specification, X1 and X2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or an alkyl group unsubstituted or substituted with deuterium, or through -CRaRb-, -NRc-, -O-, -PRd-, -S-, -PORe-, -SO 2 -, -SiRfRg-, or -BRh- It is directly connected.

본 명세서의 일 실시상태에 따르면, X1 및 X2는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 또는 중수소로 치환 또는 비치환된 탄소수 1 내지 3의 알킬기이다.According to an exemplary embodiment of the present specification, X1 and X2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or an alkyl group having 1 to 3 carbon atoms substituted or unsubstituted with deuterium.

본 명세서의 일 실시상태에 따르면, X1 및 X2는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 중수소로 치환 또는 비치환된 메틸기; 중수소로 치환 또는 비치환된 에틸기; 또는 중수소로 치환 또는 비치환된 프로필기이다.According to an exemplary embodiment of the present specification, X1 and X2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium; An ethyl group unsubstituted or substituted with deuterium; Or a propyl group unsubstituted or substituted with deuterium.

본 명세서의 일 실시상태에 따르면, X1 및 X2는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 중수소로 치환 또는 비치환된 메틸기; 중수소로 치환 또는 비치환된 에틸기; 또는 중수소로 치환 또는 비치환된 i-프로필기이다.According to an exemplary embodiment of the present specification, X1 and X2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium; An ethyl group unsubstituted or substituted with deuterium; Or an i-propyl group unsubstituted or substituted with deuterium.

본 명세서의 일 실시상태에 따르면, X1 및 X2는 -CRaRb-, -NRc-, -O-, -PRd-, -S-, -PORe-, -SO2-, -SiRfRg-, 또는 -BRh-를 통해 직접 연결된다.According to an exemplary embodiment of the present specification, X1 and X2 are -CRaRb-, -NRc-, -O-, -PRd-, -S-, -PORe-, -SO 2 -, -SiRfRg-, or -BRh- It is directly connected through.

본 명세서의 일 실시상태에 따르면, X1 및 X2는 -CRaRb-, -NRc-, -O-, -S-, -PORe-, -SO2-, -SiRfRg-, 또는 -BRh-를 통해 직접 연결된다.According to an exemplary embodiment of the present specification, X1 and X2 are directly connected through -CRaRb-, -NRc-, -O-, -S-, -PORe-, -SO 2 -, -SiRfRg-, or -BRh- do.

본 명세서의 일 실시상태에 따르면, Ra 내지 Rh는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 알키닐기; 치환 또는 비치환된 아릴알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 인접하는 기는 서로 결합하여 치환 또는 비치환된 고리를 형성한다.According to an exemplary embodiment of the present specification, Ra To Rh are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring.

본 명세서의 일 실시상태에 따르면, Ra 내지 Rh는 서로 동일하거나 상이하고, 각각 독립적으로 중수소로 치환 또는 비치환된 알킬기; 중수소로 치환 또는 비치환된 알케닐기; 중수소로 치환 또는 비치환된 알키닐기; 중수소로 치환 또는 비치환된 아릴알킬기; 중수소로 치환 또는 비치환된 아릴기; 또는 중수소로 치환 또는 비치환된 헤테로고리기이거나, 인접하는 기는 서로 결합하여 중수소 또는 중수소로 치환된 메틸기로 치환 또는 비치환된 고리를 형성한다.According to an exemplary embodiment of the present specification, Ra To Rh are the same as or different from each other, and each independently an alkyl group unsubstituted or substituted with deuterium; An alkenyl group unsubstituted or substituted with deuterium; An alkynyl group unsubstituted or substituted with deuterium; Arylalkyl group unsubstituted or substituted with deuterium; Aryl group unsubstituted or substituted with deuterium; Or a heterocyclic group substituted or unsubstituted with deuterium, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring with a methyl group substituted with deuterium or deuterium.

본 명세서의 일 실시상태에 따르면, Ra 내지 Rh는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 1 내지 30의 알킬기; 치환 또는 비치환된 탄소수 2 내지 30의 알케닐기; 치환 또는 비치환된 탄소수 2 내지 30의 알키닐기; 치환 또는 비치환된 아릴알킬기; 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 헤테로고리기이거나, 인접하는 기는 서로 결합하여 치환 또는 비치환된 탄소수 10 내지 30의 방향족 탄화수소고리 또는 치환 또는 비치환된 탄소수 12 내지 30의 헤테로고리를 형성한다.According to an exemplary embodiment of the present specification, Ra To Rh are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms; A substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or adjacent groups are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 10 to 30 carbon atoms or a substituted or unsubstituted heterocyclic ring having 12 to 30 carbon atoms do.

본 명세서의 일 실시상태에 따르면, Ra 내지 Rh는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 1 내지 20의 알킬기; 치환 또는 비치환된 탄소수 2 내지 20의 알케닐기; 치환 또는 비치환된 탄소수 2 내지 20의 알키닐기; 치환 또는 비치환된 아릴알킬기; 치환 또는 비치환된 탄소수 6 내지 20의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 20의 헤테로고리기이거나, 인접하는 기는 서로 결합하여 치환 또는 비치환된 탄소수 10 내지 20의 방향족 탄화수소고리 또는 치환 또는 비치환된 탄소수 12 내지 20의 헤테로고리를 형성한다.According to an exemplary embodiment of the present specification, Ra To Rh are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms; A substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms, or adjacent groups are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 10 to 20 carbon atoms or a substituted or unsubstituted heterocycle having 12 to 20 carbon atoms do.

본 명세서의 일 실시상태에 따르면, Ra 내지 Rh는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 1 내지 10의 알킬기; 치환 또는 비치환된 탄소수 2 내지 10의 알케닐기; 치환 또는 비치환된 탄소수 2 내지 10의 알키닐기; 치환 또는 비치환된 아릴알킬기; 치환 또는 비치환된 탄소수 6 내지 10의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 10의 헤테로고리기이거나, 인접하는 기는 서로 결합하여 치환 또는 비치환된 탄소수 10 내지 20의 방향족 탄화수소고리 또는 치환 또는 비치환된 탄소수 12 내지 20의 헤테로고리를 형성한다.According to an exemplary embodiment of the present specification, Ra To Rh are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms; A substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted aryl group having 6 to 10 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 10 carbon atoms, or adjacent groups are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 10 to 20 carbon atoms or a substituted or unsubstituted heterocycle having 12 to 20 carbon atoms do.

본 명세서의 일 실시상태에 따르면, Ra 내지 Rh는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 인접하는 기는 서로 결합하여 치환 또는 비치환된 방향족 탄화수소고리 또는 치환 또는 비치환된 헤테로고리를 형성한다.According to an exemplary embodiment of the present specification, Ra To Rh are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heterocycle.

본 명세서의 일 실시상태에 따르면, Ra 내지 Rh는 서로 동일하거나 상이하고, 각각 독립적으로 중수소로 치환 또는 비치환된 알킬기; 중수소로 치환 또는 비치환된 아릴기; 또는 중수소로 치환 또는 비치환된 헤테로고리기이거나, 인접하는 기는 서로 결합하여 중수소로 치환 또는 비치환된 방향족 탄화수소고리 또는 치환 또는 비치환된 헤테로고리를 형성한다.According to an exemplary embodiment of the present specification, Ra To Rh are the same as or different from each other, and each independently an alkyl group unsubstituted or substituted with deuterium; Aryl group unsubstituted or substituted with deuterium; Or a heterocyclic group substituted or unsubstituted with deuterium, or adjacent groups are bonded to each other to form an aromatic hydrocarbon ring substituted or unsubstituted with deuterium or a substituted or unsubstituted heterocycle.

본 명세서의 일 실시상태에 따르면, Ra 내지 Rh는 서로 동일하거나 상이하고, 각각 독립적으로 중수소 또는 CD3로 치환 또는 비치환된 알킬기; 중수소 또는 CD3로 치환 또는 비치환된 아릴기; 또는 중수소 또는 CD3로 치환 또는 비치환된 헤테로고리기이거나, 인접하는 기는 서로 결합하여 중수소 또는 CD3로 치환 또는 비치환된 방향족 탄화수소고리 또는 중수소 또는 CD3로 치환 또는 비치환된 헤테로고리를 형성한다.According to an exemplary embodiment of the present specification, Ra To Rh are the same as or different from each other, and each independently an alkyl group unsubstituted or substituted with deuterium or CD 3; Aryl group unsubstituted or substituted with deuterium or CD 3; Or deuterium, or substituted with a CD 3 or unsubstituted heterocyclic group, or form a substituted or unsubstituted heterocyclic group with the adjacent deuterium or CD 3 groups are bonded to each other to a substituted or unsubstituted aromatic hydrocarbon ring or a deuterium or CD 3 ring do.

본 명세서의 일 실시상태에 따르면, Ra 내지 Rh는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 메틸기; 또는 치환 또는 비치환된 페닐기이거나, 인접하는 기는 서로 결합하여 치환 또는 비치환된 플루오렌 고리; 또는 치환 또는 비치환된 하기 구조를 형성한다. 하기 구조에서,

Figure PCTKR2020012249-appb-I000027
는 고리를 형성하는 위치를 의미한다.According to an exemplary embodiment of the present specification, Ra To Rh are the same as or different from each other, and each independently a substituted or unsubstituted methyl group; Or a substituted or unsubstituted phenyl group, or adjacent groups are bonded to each other to form a substituted or unsubstituted fluorene ring; Or it forms the following structure which is substituted or unsubstituted. In the following structure,
Figure PCTKR2020012249-appb-I000027
Means a position to form a ring.

Figure PCTKR2020012249-appb-I000028
Figure PCTKR2020012249-appb-I000028

본 명세서의 일 실시상태에 따르면, Ra 내지 Rh는 서로 동일하거나 상이하고, 각각 독립적으로 중수소로 치환 또는 비치환된 메틸기; 또는 중수소, 메틸기 및 헥사하이드로카바졸기로 이루어진 군에서 선택된 1 이상의 기 또는 2 이상이 연결된 기로 치환 또는 비치환된 페닐기이거나, 인접하는 기는 서로 결합하여 플루오렌 고리; 또는 하기 구조를 형성한다. 하기 구조는 CD3로 치환 또는 비치환된 페닐기로 치환 또는 비치환되고,

Figure PCTKR2020012249-appb-I000029
는 고리를 형성하는 위치를 의미한다.According to an exemplary embodiment of the present specification, Ra To Rh are the same as or different from each other, and each independently a methyl group unsubstituted or substituted with deuterium; Or a phenyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a methyl group, and a hexahydrocarbazole group, or a group to which two or more are connected, or adjacent groups are bonded to each other to form a fluorene ring; Or to form the following structure. The following structure is unsubstituted or substituted with a phenyl group unsubstituted or substituted with CD 3,
Figure PCTKR2020012249-appb-I000029
Means a position to form a ring.

Figure PCTKR2020012249-appb-I000030
Figure PCTKR2020012249-appb-I000030

본 명세서의 일 실시상태에 따르면, Ra 내지 Rh는 서로 동일하거나 상이하고, 각각 독립적으로 CD3; 메틸기; 또는 CD3 또는 CD3로 치환된 헥사하이드로카바졸기로 치환 또는 비치환된 페닐기이거나, 인접하는 기는 서로 결합하여 플루오렌 고리; 또는 하기 구조를 형성한다. 하기 구조는 CD3로 치환 또는 비치환된 페닐기로 치환 또는 비치환되고,

Figure PCTKR2020012249-appb-I000031
는 고리를 형성하는 위치를 의미한다.According to an exemplary embodiment of the present specification, Ra To Rh are the same as or different from each other, and each independently CD 3 ; Methyl group; Or a phenyl group unsubstituted or substituted with a hexahydrocarbazole group substituted with CD 3 or CD 3 , or adjacent groups bonded to each other to form a fluorene ring; Or to form the following structure. The following structure is unsubstituted or substituted with a phenyl group unsubstituted or substituted with CD 3,
Figure PCTKR2020012249-appb-I000031
Means a position to form a ring.

Figure PCTKR2020012249-appb-I000032
Figure PCTKR2020012249-appb-I000032

본 명세서의 일 실시상태에 따르면, R1 내지 R5는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알킬티오기; 치환 또는 비치환된 아릴티오기; 치환 또는 비치환된 알킬술포닐기; 치환 또는 비치환된 아릴술포닐기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 아릴알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 인접하는 기는 서로 결합하여 치환 또는 비치환된 고리를 형성한다.According to an exemplary embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfonyl group; A substituted or unsubstituted arylsulfonyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring.

본 명세서의 일 실시상태에 따르면, R1 내지 R5는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 30의 알킬기; 치환 또는 비치환된 탄소수 1 내지 30의 알콕시기; 치환 또는 비치환된 탄소수 6 내지 30의 아릴옥시기; 치환 또는 비치환된 탄소수 1 내지 30의 알킬티오기; 치환 또는 비치환된 탄소수 6 내지 30의 아릴티오기; 치환 또는 비치환된 탄소수 1 내지 30의 알킬술포닐기; 치환 또는 비치환된 탄소수 6 내지 30의 아릴술포닐기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 탄소수 1 내지 30의 아릴알킬기; 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기; 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 헤테로고리기이거나, 인접하는 기는 서로 결합하여 치환 또는 비치환된 탄소수 2 내지 30의 고리를 형성한다.According to an exemplary embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C30 alkyl group; A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms; A substituted or unsubstituted C1 to C30 alkylthio group; A substituted or unsubstituted arylthio group having 6 to 30 carbon atoms; A substituted or unsubstituted C 1 to C 30 alkylsulfonyl group; A substituted or unsubstituted arylsulfonyl group having 6 to 30 carbon atoms; A substituted or unsubstituted amine group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted arylalkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring having 2 to 30 carbon atoms.

본 명세서의 일 실시상태에 따르면, R1 내지 R5는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 20의 알킬기; 치환 또는 비치환된 탄소수 1 내지 20의 알콕시기; 치환 또는 비치환된 탄소수 6 내지 20의 아릴옥시기; 치환 또는 비치환된 탄소수 1 내지 20의 알킬티오기; 치환 또는 비치환된 탄소수 6 내지 20의 아릴티오기; 치환 또는 비치환된 탄소수 1 내지 20의 알킬술포닐기; 치환 또는 비치환된 탄소수 6 내지 20의 아릴술포닐기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 탄소수 1 내지 20의 아릴알킬기; 치환 또는 비치환된 탄소수 3 내지 20의 시클로알킬기; 치환 또는 비치환된 탄소수 6 내지 20의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 20의 헤테로고리기이거나, 인접하는 기는 서로 결합하여 치환 또는 비치환된 탄소수 2 내지 20의 고리를 형성한다.According to an exemplary embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; A substituted or unsubstituted aryloxy group having 6 to 20 carbon atoms; A substituted or unsubstituted C1 to C20 alkylthio group; A substituted or unsubstituted arylthio group having 6 to 20 carbon atoms; A substituted or unsubstituted C 1 to C 20 alkylsulfonyl group; A substituted or unsubstituted arylsulfonyl group having 6 to 20 carbon atoms; A substituted or unsubstituted amine group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted arylalkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted C3 to C20 cycloalkyl group; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring having 2 to 20 carbon atoms.

본 명세서의 일 실시상태에 따르면, R1 내지 R5는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 10의 알킬기; 치환 또는 비치환된 탄소수 1 내지 10의 알콕시기; 치환 또는 비치환된 탄소수 6 내지 14의 아릴옥시기; 치환 또는 비치환된 탄소수 1 내지 10의 알킬티오기; 치환 또는 비치환된 탄소수 6 내지 14의 아릴티오기; 치환 또는 비치환된 탄소수 1 내지 10의 알킬술포닐기; 치환 또는 비치환된 탄소수 6 내지 14의 아릴술포닐기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 탄소수 1 내지 14의 아릴알킬기; 치환 또는 비치환된 탄소수 3 내지 10의 시클로알킬기; 치환 또는 비치환된 탄소수 6 내지 14의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 14의 헤테로고리기이거나, 인접하는 기는 서로 결합하여 치환 또는 비치환된 탄소수 2 내지 14의 고리를 형성한다.According to an exemplary embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms; A substituted or unsubstituted aryloxy group having 6 to 14 carbon atoms; A substituted or unsubstituted C1 to C10 alkylthio group; A substituted or unsubstituted arylthio group having 6 to 14 carbon atoms; A substituted or unsubstituted C 1 to C 10 alkylsulfonyl group; A substituted or unsubstituted arylsulfonyl group having 6 to 14 carbon atoms; A substituted or unsubstituted amine group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted arylalkyl group having 1 to 14 carbon atoms; A substituted or unsubstituted C 3 to C 10 cycloalkyl group; A substituted or unsubstituted aryl group having 6 to 14 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 14 carbon atoms, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring having 2 to 14 carbon atoms.

본 명세서의 일 실시상태에 따르면, R1 내지 R5는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 중수소, 할로겐기, 알킬기, 아릴기 및 헤테로고리기로 이루어진 군에서 선택된 1 이상의 기 또는 2 이상이 연결된 기로 치환 또는 비치환된 알킬기; 중수소, 할로겐기, 알킬기, 아릴기 및 헤테로고리기로 이루어진 군에서 선택된 1 이상의 기 또는 2 이상이 연결된 기로 치환 또는 비치환된 알콕시기; 중수소, 할로겐기, 알킬기, 아릴기 및 헤테로고리기로 이루어진 군에서 선택된 1 이상의 기 또는 2 이상이 연결된 기로 치환 또는 비치환된 아릴옥시기; 중수소, 할로겐기, 알킬기, 아릴기 및 헤테로고리기로 이루어진 군에서 선택된 1 이상의 기 또는 2 이상이 연결된 기로 치환 또는 비치환된 알킬티오기; 중수소, 할로겐기, 알킬기, 아릴기 및 헤테로고리기로 이루어진 군에서 선택된 1 이상의 기 또는 2 이상이 연결된 기로 치환 또는 비치환된 아릴티오기; 중수소, 할로겐기, 알킬기, 아릴기 및 헤테로고리기로 이루어진 군에서 선택된 1 이상의 기 또는 2 이상이 연결된 기로 치환 또는 비치환된 알킬술포닐기; 중수소, 할로겐기, 알킬기, 아릴기 및 헤테로고리기로 이루어진 군에서 선택된 1 이상의 기 또는 2 이상이 연결된 기로 치환 또는 비치환된 아릴술포닐기; 중수소, 할로겐기, 알킬기, 아릴기 및 헤테로고리기로 이루어진 군에서 선택된 1 이상의 기 또는 2 이상이 연결된 기로 치환 또는 비치환된 아민기; 중수소, 할로겐기, 알킬기, 아릴기 및 헤테로고리기로 이루어진 군에서 선택된 1 이상의 기 또는 2 이상이 연결된 기로 치환 또는 비치환된 실릴기; 중수소, 할로겐기, 알킬기, 아릴기 및 헤테로고리기로 이루어진 군에서 선택된 1 이상의 기 또는 2 이상이 연결된 기로 치환 또는 비치환된 붕소기; 중수소, 할로겐기, 알킬기, 아릴기 및 헤테로고리기로 이루어진 군에서 선택된 1 이상의 기 또는 2 이상이 연결된 기로 치환 또는 비치환된 아릴알킬기; 중수소, 할로겐기, 알킬기, 아릴기 및 헤테로고리기로 이루어진 군에서 선택된 1 이상의 기 또는 2 이상이 연결된 기로 치환 또는 비치환된 시클로알킬기; 중수소, 할로겐기, 알킬기, 아릴기 및 헤테로고리기로 이루어진 군에서 선택된 1 이상의 기 또는 2 이상이 연결된 기로 치환 또는 비치환된 아릴기; 또는 중수소, 할로겐기, 알킬기, 아릴기 및 헤테로고리기로 이루어진 군에서 선택된 1 이상의 기 또는 2 이상이 연결된 기로 치환 또는 비치환된 헤테로고리기이거나, 인접하는 기는 서로 결합하여 중수소, 할로겐기, 알킬기, 아릴기 및 헤테로고리기로 이루어진 군에서 선택된 1 이상의 기 또는 2 이상이 연결된 기로 치환 또는 비치환된 고리를 형성한다.According to an exemplary embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; An alkyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a halogen group, an alkyl group, an aryl group, and a heterocyclic group, or a group to which two or more are connected; An alkoxy group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a halogen group, an alkyl group, an aryl group, and a heterocyclic group, or a group to which two or more are connected; An aryloxy group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a halogen group, an alkyl group, an aryl group, and a heterocyclic group, or a group to which two or more are connected; An alkylthio group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a halogen group, an alkyl group, an aryl group, and a heterocyclic group, or a group to which two or more are connected; An arylthio group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a halogen group, an alkyl group, an aryl group, and a heterocyclic group, or a group to which two or more are connected; An alkylsulfonyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a halogen group, an alkyl group, an aryl group, and a heterocyclic group, or a group to which two or more are connected; An arylsulfonyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a halogen group, an alkyl group, an aryl group, and a heterocyclic group, or a group to which two or more are connected; An amine group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a halogen group, an alkyl group, an aryl group, and a heterocyclic group, or a group to which two or more are connected; A silyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a halogen group, an alkyl group, an aryl group, and a heterocyclic group, or a group to which two or more are connected; A boron group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a halogen group, an alkyl group, an aryl group, and a heterocyclic group, or a group to which two or more are connected; An arylalkyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a halogen group, an alkyl group, an aryl group, and a heterocyclic group, or a group to which two or more are connected; A cycloalkyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a halogen group, an alkyl group, an aryl group, and a heterocyclic group, or a group to which two or more are connected; An aryl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a halogen group, an alkyl group, an aryl group, and a heterocyclic group, or a group to which two or more are connected; Or a heterocyclic group substituted or unsubstituted with one or more groups selected from the group consisting of deuterium, a halogen group, an alkyl group, an aryl group and a heterocyclic group, or a group to which two or more are connected, or adjacent groups are bonded to each other to form deuterium, a halogen group, an alkyl group, One or more groups selected from the group consisting of an aryl group and a heterocyclic group, or a group to which two or more are connected to form a substituted or unsubstituted ring.

본 명세서의 일 실시상태에 따르면, R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 메틸기; 치환 또는 비치환된 에틸기; 치환 또는 비치환된 프로필기; 치환 또는 비치환된 부틸기; 치환 또는 비치환된 펜틸기; 치환 또는 비치환된 메톡시기; 치환 또는 비치환된 메틸티오기; 치환 또는 비치환된 페닐티오기; 치환 또는 비치환된 메틸술포닐기; 치환 또는 비치환된 t-부틸술포닐기; 치환 또는 비치환된 페닐술포닐기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 트리메틸실릴기; 치환 또는 비치환된 트리페닐실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 시클로펜틸기; 치환 또는 비치환된 시클로헥실기; 치환 또는 비치환된 페닐프로필기; 치환 또는 비치환된 페닐기; 치환 또는 비치환된 카바졸기; 치환 또는 비치환된 피리딜기; 또는 치환 또는 비치환된 헥사하이드로카바졸기이거나, R3 또는 R5와 직접결합; 또는 치환 또는 비치환된 페닐기로 치환된 B를 통하여 결합하거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 페난트렌 고리; 치환 또는 비치환된 인덴 고리; 치환 또는 비치환된 벤조퓨란 고리; 치환 또는 비치환된 벤조티오펜 고리; 치환 또는 비치환된 인돌 고리; 치환 또는 비치환된 카바졸 고리; 치환 또는 비치환된 시클로펜텐 고리; 치환 또는 비치환된 시클로헥센 고리; 환 또는 비치환된 시클로헵텐 고리; 치환 또는 비치환된 테트라하이드로나프탈렌 고리; 치환 또는 비치환된 다이하이드로벤조다이옥신(dihydrobenzo[b]dioxine)고리; 치환 또는 비치환된 테트라하이드로에타노나프탈렌(tetrahydroethanonaphthalene) 고리; 치환 또는 비치환된 바이사이클로헵텐 고리; 치환 또는 비치환된 바이사이클로옥텐 고리; 또는 치환 또는 비치환된 헥사하이드로카바졸기를 형성한다. 상기 기들은 중수소, 할로겐기, 탄소수 1 내지 10의 알킬기 및 탄소수 6 내지 20의 아릴기로 이루어진 군에서 선택된 1 이상의 기 또는 2 이상의 기가 결합된 기로 치환 또는 비치환된다.According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted pentyl group; A substituted or unsubstituted methoxy group; A substituted or unsubstituted methylthio group; A substituted or unsubstituted phenylthio group; A substituted or unsubstituted methylsulfonyl group; A substituted or unsubstituted t-butylsulfonyl group; A substituted or unsubstituted phenylsulfonyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted trimethylsilyl group; A substituted or unsubstituted triphenylsilyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted cyclopentyl group; A substituted or unsubstituted cyclohexyl group; A substituted or unsubstituted phenylpropyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted pyridyl group; Or a substituted or unsubstituted hexahydrocarbazole group, or a direct bond with R3 or R5; Or a substituted or unsubstituted phenanthrene ring by bonding through B substituted with a substituted or unsubstituted phenyl group, or by bonding with an adjacent group to each other; A substituted or unsubstituted indene ring; A substituted or unsubstituted benzofuran ring; Substituted or unsubstituted benzothiophene ring; A substituted or unsubstituted indole ring; Substituted or unsubstituted carbazole ring; A substituted or unsubstituted cyclopentene ring; A substituted or unsubstituted cyclohexene ring; Ring or unsubstituted cycloheptene ring; A substituted or unsubstituted tetrahydronaphthalene ring; A substituted or unsubstituted dihydrobenzo[b]dioxine ring; A substituted or unsubstituted tetrahydroethanonaphthalene ring; A substituted or unsubstituted bicycloheptene ring; A substituted or unsubstituted bicyclooctene ring; Or a substituted or unsubstituted hexahydrocarbazole group is formed. The groups are substituted or unsubstituted with one or more groups selected from the group consisting of deuterium, a halogen group, an alkyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 20 carbon atoms, or a group to which two or more groups are bonded.

본 명세서의 일 실시상태에 따르면, R1 및 R2는 중수소, -F, 메틸기, CD3, i-프로필기, t-부틸기 및 페닐기로 이루어진 군에서 선택된 1 이상의 기 또는 2 이상의 기가 결합된 기로 치환 또는 비치환된다.According to an exemplary embodiment of the present specification, R1 and R2 are substituted with one or more groups selected from the group consisting of deuterium, -F, methyl group, CD 3 , i-propyl group, t-butyl group, and phenyl group, or a group to which two or more groups are bonded. Or unsubstituted.

본 명세서의 일 실시상태에 따르면, R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 중수소 또는 -F로 치환 또는 비치환된 메틸기; 중수소 또는 -F로 치환 또는 비치환된 에틸기; 중수소, -F 및 페닐기로 이루어진 군에서 선택된 1 이상의 기 또는 2 이상이 연결된 기로 치환 또는 비치환된 프로필기; 중수소 또는 -F로 치환 또는 비치환된 부틸기; 중수소 또는 -F로 치환 또는 비치환된 펜틸기; 중수소 또는 -F로 치환 또는 비치환된 메톡시기; 중수소 또는 -F로 치환 또는 비치환된 메틸티오기; 중수소, 메틸기 또는 CD3로 치환 또는 비치환된 페닐티오기; 중수소로 치환 또는 비치환된 메틸술포닐기; 중수소로 치환 또는 비치환된 t-부틸술포닐기; 중수소, 메틸기 또는 CD3로 치환 또는 비치환된 페닐술포닐기; 중수소, -F, 메틸기 또는 CD3로 치환 또는 비치환된 페닐기 또는 CD3로 치환된 아민기; 중수소로 치환 또는 비치환된 트리메틸실릴기; 중수소, 메틸기 또는 CD3로 치환 또는 비치환된 트리페닐실릴기; 중수소, 메틸기 또는 CD3로 치환 또는 비치환된 페닐기로 치환 또는 비치환된 붕소기; 중수소, 메틸기 또는 CD3로 치환 또는 비치환된 시클로펜틸기; 중수소, 메틸기 또는 CD3로 치환 또는 비치환된 시클로헥실기; 중수소, 메틸기 또는 CD3로 치환 또는 비치환된 페닐프로필기; 중수소, -F, 메틸기 또는 CD3로 치환 또는 비치환된 페닐기; 중수소, 메틸기, CD3, t-부틸기 및 페닐기로 이루어진 군에서 선택된 1 이상의 기 또는 2 이상의 기가 연결된 기로 치환 또는 비치환된 카바졸기; CD3로 치환 또는 비치환된 피리딜기; 또는 메틸기, CD3 또는 t-부틸기로 치환 또는 비치환된 헥사하이드로카바졸기이거나, R3 또는 R5와 직접결합; 또는 CD3로 치환 또는 비치환된 페닐기로 치환된 B를 통하여 결합하거나, 인접하는 기와 서로 결합하여 중수소, 메틸기 또는 CD3로 치환 또는 비치환된 페난트렌 고리; 메틸기 또는 CD3로 치환 또는 비치환된 인덴 고리; 중수소, 메틸기, CD3 또는 t-부틸기로 치환 또는 비치환된 벤조퓨란 고리; 중수소, 메틸기 또는 CD3로 치환 또는 비치환된 벤조티오펜 고리; CD3 및 페닐기로 이루어진 군에서 선택된 1 이상의 기 또는 2 이상의 기가 결합된 기로 치환 또는 비치환된 인돌 고리; 중수소, 메틸기, t-부틸기 및 페닐기로 이루어진 군에서 선택된 1 이상의 기 또는 2 이상의 기가 결합된 기로 치환 또는 비치환된 카바졸 고리; 중수소, 메틸기 또는 CD3로 치환 또는 비치환된 시클로펜텐 고리; 중수소, 메틸기 또는 CD3로 치환 또는 비치환된 시클로헥센 고리; 중수소, 메틸기 또는 CD3로 치환 또는 비치환된 시클로헵텐 고리; 중수소, 메틸기 또는 CD3로 치환 또는 비치환된 테트라하이드로나프탈렌 고리; 중수소, 메틸기 또는 CD3로 치환 또는 비치환된 다이하이드로벤조다이옥신(dihydrobenzo[b]dioxine)고리; 중수소, 메틸기 또는 CD3로 치환 또는 비치환된 테트라하이드로에타노나프탈렌(tetrahydroethanonaphthalene) 고리; 중수소, 메틸기 또는 CD3로 치환 또는 비치환된 바이사이클로헵텐 고리; 중수소, 메틸기 또는 CD3로 치환 또는 비치환된 바이사이클로옥텐 고리; 또는 중수소, 메틸기, CD3, t-부틸기로 치환 또는 비치환된 헥사하이드로카바졸기를 형성한다.According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium or -F; An ethyl group unsubstituted or substituted with deuterium or -F; A propyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, -F and a phenyl group, or a group to which two or more are connected; A butyl group unsubstituted or substituted with deuterium or -F; A pentyl group unsubstituted or substituted with deuterium or -F; A methoxy group unsubstituted or substituted with deuterium or -F; A methylthio group unsubstituted or substituted with deuterium or -F; A phenylthio group unsubstituted or substituted with deuterium, a methyl group, or CD 3; A methylsulfonyl group unsubstituted or substituted with deuterium; T-butylsulfonyl group unsubstituted or substituted with deuterium; A phenylsulfonyl group unsubstituted or substituted with deuterium, a methyl group, or CD 3; Deuterium, -F, a phenyl group unsubstituted or substituted with a methyl group or CD 3 or an amine group substituted with a CD 3; Trimethylsilyl group unsubstituted or substituted with deuterium; Triphenylsilyl group unsubstituted or substituted with deuterium, methyl group, or CD 3; A boron group unsubstituted or substituted with deuterium, a methyl group, or a phenyl group unsubstituted or substituted with CD 3; A cyclopentyl group unsubstituted or substituted with deuterium, a methyl group, or CD 3; A cyclohexyl group unsubstituted or substituted with deuterium, a methyl group, or CD 3; A phenylpropyl group unsubstituted or substituted with deuterium, a methyl group, or CD 3; A phenyl group unsubstituted or substituted with deuterium, -F, a methyl group or CD 3; A carbazole group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, methyl group, CD 3 , t-butyl group and phenyl group or a group to which two or more groups are linked; A pyridyl group unsubstituted or substituted with CD 3; Or a hexahydrocarbazole group unsubstituted or substituted with a methyl group, CD 3 or t-butyl group, or a direct bond with R3 or R5; Or a phenanthrene ring unsubstituted or substituted with deuterium, a methyl group, or CD 3 by bonding through B substituted with a phenyl group substituted or unsubstituted with CD 3, or bonded to each other with an adjacent group; An indene ring unsubstituted or substituted with a methyl group or CD 3; Benzofuran ring unsubstituted or substituted with deuterium, methyl group, CD 3 or t-butyl group; Benzothiophene ring unsubstituted or substituted with deuterium, methyl group, or CD 3; An indole ring unsubstituted or substituted with one or more groups selected from the group consisting of CD 3 and a phenyl group or a group to which two or more groups are bonded; A carbazole ring unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, a methyl group, a t-butyl group, and a phenyl group, or a group to which two or more groups are bonded; A cyclopentene ring unsubstituted or substituted with deuterium, a methyl group, or CD 3; A cyclohexene ring unsubstituted or substituted with deuterium, a methyl group, or CD 3; A cycloheptene ring unsubstituted or substituted with deuterium, a methyl group, or CD 3; Tetrahydronaphthalene ring unsubstituted or substituted with deuterium, methyl group, or CD 3; Dihydrobenzo[b]dioxine ring unsubstituted or substituted with deuterium, methyl group, or CD 3; Tetrahydroethanonaphthalene ring unsubstituted or substituted with deuterium, methyl group, or CD 3; Bicycloheptene ring unsubstituted or substituted with deuterium, methyl group, or CD 3; Bicyclooctene ring unsubstituted or substituted with deuterium, methyl group, or CD 3; Or a deuterium, methyl group, CD 3 , t-butyl group to form a substituted or unsubstituted hexahydrocarbazole group.

본 명세서의 일 실시상태에 따르면, R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 중수소 또는 -F로 치환 또는 비치환된 메틸기; 중수소로 치환 또는 비치환된 에틸기; 중수소 및 페닐기로 이루어진 군에서 선택된 1 이상의 기 또는 2 이상이 연결된 기로 치환 또는 비치환된 i-프로필기; t-부틸기; t-펜틸기; 중수소 또는 -F로 치환 또는 비치환된 메톡시기; 중수소 또는 -F로 치환 또는 비치환된 메틸티오기; 페닐티오기; 중수소로 치환 또는 비치환된 메틸술포닐기; 중수소로 치환 또는 비치환된 t-부틸술포닐기; 페닐술포닐기; 중수소, -F, 메틸기 또는 CD3로 치환 또는 비치환된 페닐기 또는 CD3로 치환된 아민기; 중수소로 치환 또는 비치환된 트리메틸실릴기; 트리페닐실릴기; 디페닐붕소기; 중수소 또는 CD3로 치환 또는 비치환된 시클로펜틸기; 중수소 또는 CD3로 치환 또는 비치환된 시클로헥실기; 중수소로 치환 또는 비치환된 페닐프로필기; 중수소, -F 또는 CD3로 치환 또는 비치환된 페닐기; 중수소, 메틸기, CD3, t-부틸기 및 페닐기로 이루어진 군에서 선택된 1 이상의 기 또는 2 이상의 기가 연결된 기로 치환 또는 비치환된 카바졸기; CD3로 치환 또는 비치환된 피리딜기; 또는 메틸기, CD3 또는 t-부틸기로 치환 또는 비치환된 헥사하이드로카바졸기이거나, R3 또는 R5와 직접결합; 또는 CD3로 치환 또는 비치환된 페닐기로 치환된 B를 통하여 결합하거나, 인접하는 기와 서로 결합하여 페난트렌 고리; 메틸기 또는 CD3로 치환 또는 비치환된 인덴 고리; CD3 또는 t-부틸기로 치환 또는 비치환된 벤조퓨란 고리; 중수소로 치환 또는 비치환된 벤조티오펜 고리; CD3 및 페닐기로 이루어진 군에서 선택된 1 이상의 기 또는 2 이상의 기가 결합된 기로 치환 또는 비치환된 인돌 고리; CD3, t-부틸기 및 페닐기로 이루어진 군에서 선택된 1 이상의 기 또는 2 이상의 기가 결합된 기로 치환 또는 비치환된 카바졸 고리; 중수소, 메틸기 또는 CD3로 치환 또는 비치환된 시클로펜텐 고리; 중수소, 메틸기 또는 CD3로 치환 또는 비치환된 시클로헥센 고리; 중수소로 치환 또는 비치환된 시클로헵텐 고리; 중수소, 메틸기 또는 CD3로 치환 또는 비치환된 테트라하이드로나프탈렌 고리; 중수소로 치환 또는 비치환된 다이하이드로벤조다이옥신(dihydrobenzo[b]dioxine)고리; 테트라하이드로에타노나프탈렌(tetrahydroethanonaphthalene) 고리; 메틸기로 치환 또는 비치환된 바이사이클로헵텐 고리; 메틸기로 치환 또는 비치환된 바이사이클로옥텐 고리; 또는 메틸기 또는 t-부틸기로 치환 또는 비치환된 헥사하이드로카바졸기를 형성한다.According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium or -F; An ethyl group unsubstituted or substituted with deuterium; An i-propyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium and a phenyl group or a group to which two or more are connected; t-butyl group; t-pentyl group; A methoxy group unsubstituted or substituted with deuterium or -F; A methylthio group unsubstituted or substituted with deuterium or -F; Phenylthio group; A methylsulfonyl group unsubstituted or substituted with deuterium; T-butylsulfonyl group unsubstituted or substituted with deuterium; Phenylsulfonyl group; Deuterium, -F, a phenyl group unsubstituted or substituted with a methyl group or CD 3 or an amine group substituted with a CD 3; Trimethylsilyl group unsubstituted or substituted with deuterium; Triphenylsilyl group; Diphenylboron group; A cyclopentyl group unsubstituted or substituted with deuterium or CD 3; A cyclohexyl group unsubstituted or substituted with deuterium or CD 3; A phenylpropyl group unsubstituted or substituted with deuterium; A phenyl group unsubstituted or substituted with deuterium, -F or CD 3; A carbazole group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, methyl group, CD 3 , t-butyl group and phenyl group or a group to which two or more groups are linked; A pyridyl group unsubstituted or substituted with CD 3; Or a hexahydrocarbazole group unsubstituted or substituted with a methyl group, CD 3 or t-butyl group, or a direct bond with R3 or R5; Or a phenanthrene ring by bonding through B substituted with a phenyl group substituted or unsubstituted with CD 3 or by bonding with an adjacent group to each other; An indene ring unsubstituted or substituted with a methyl group or CD 3; Benzofuran ring unsubstituted or substituted with CD 3 or t-butyl group; A benzothiophene ring unsubstituted or substituted with deuterium; An indole ring unsubstituted or substituted with one or more groups selected from the group consisting of CD 3 and a phenyl group or a group to which two or more groups are bonded; CD 3 , a carbazole ring unsubstituted or substituted with one or more groups selected from the group consisting of t-butyl group and a phenyl group or a group to which two or more groups are bonded; A cyclopentene ring unsubstituted or substituted with deuterium, a methyl group, or CD 3; A cyclohexene ring unsubstituted or substituted with deuterium, a methyl group, or CD 3; A cycloheptene ring unsubstituted or substituted with deuterium; Tetrahydronaphthalene ring unsubstituted or substituted with deuterium, methyl group, or CD 3; Dihydrobenzo[b]dioxine ring unsubstituted or substituted with deuterium; Tetrahydroethanonaphthalene ring; A bicycloheptene ring unsubstituted or substituted with a methyl group; A bicyclooctene ring unsubstituted or substituted with a methyl group; Or a methyl group or a t-butyl group substituted or unsubstituted hexahydrocarbazole group is formed.

본 명세서의 일 실시상태에 따르면, R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 중수소 또는 -F로 치환 또는 비치환된 메틸기; 중수소로 치환 또는 비치환된 에틸기; 중수소 및 페닐기로 이루어진 군에서 선택된 1 이상의 기 또는 2 이상이 연결된 기로 치환 또는 비치환된 i-프로필기; t-부틸기; t-펜틸기; 중수소 또는 -F로 치환 또는 비치환된 메톡시기; 중수소, -F, 메틸기 또는 CD3로 치환 또는 비치환된 페닐기 또는 CD3로 치환된 아민기; 중수소로 치환 또는 비치환된 트리메틸실릴기; 또는 중수소, -F 또는 CD3로 치환 또는 비치환된 페닐기이거나, 인접하는 기와 서로 결합하여 CD3 또는 t-부틸기로 치환 또는 비치환된 벤조퓨란 고리; 중수소로 치환 또는 비치환된 벤조티오펜 고리; 중수소, 메틸기 또는 CD3로 치환 또는 비치환된 시클로헥센 고리; 중수소로 치환 또는 비치환된 시클로헵텐 고리; 테트라하이드로에타노나프탈렌(tetrahydroethanonaphthalene) 고리; 또는 메틸기 또는 t-부틸기로 치환 또는 비치환된 헥사하이드로카바졸기를 형성한다.According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium or -F; An ethyl group unsubstituted or substituted with deuterium; An i-propyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium and a phenyl group or a group to which two or more are connected; t-butyl group; t-pentyl group; A methoxy group unsubstituted or substituted with deuterium or -F; Deuterium, -F, a phenyl group unsubstituted or substituted with a methyl group or CD 3 or an amine group substituted with a CD 3; Trimethylsilyl group unsubstituted or substituted with deuterium; Or a phenyl group unsubstituted or substituted with deuterium, -F or CD 3 , or a benzofuran ring unsubstituted or substituted with a CD 3 or t-butyl group by bonding with an adjacent group; A benzothiophene ring unsubstituted or substituted with deuterium; A cyclohexene ring unsubstituted or substituted with deuterium, a methyl group, or CD 3; A cycloheptene ring unsubstituted or substituted with deuterium; Tetrahydroethanonaphthalene ring; Or a methyl group or a t-butyl group substituted or unsubstituted hexahydrocarbazole group is formed.

본 명세서의 일 실시상태에 따르면, R3 및 R5는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 메틸기; 치환 또는 비치환된 에틸기; 치환 또는 비치환된 프로필기; 치환 또는 비치환된 부틸기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 페닐프로필기; 치환 또는 비치환된 아다만틸기; 치환 또는 비치환된 페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 디벤조퓨란기; 치환 또는 비치환된 피리딜기; 치환 또는 비치환된 카바졸기이거나, R1 또는 R2와 직접결합; 또는 치환 또는 비치환된 B를 통하여 결합하거나, 인접하는 기는 서로 결합하여 치환 또는 비치환된 페난트렌 고리; 치환 또는 비치환된 인덴 고리; 치환 또는 비치환된 시클로펜텐 고리; 치환 또는 비치환된 시클로헥센 고리; 또는 치환 또는 비치환된 벤조퓨란 고리를 형성한다. 상기 기들은 중수소, 할로겐기, 탄소수 1 내지 10의 알킬기 및 탄소수 6 내지 20의 아릴기로 이루어진 군에서 선택된 1 이상의 기 또는 2 이상의 기가 결합된 기로 치환 또는 비치환된다.According to an exemplary embodiment of the present specification, R3 and R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted phenylpropyl group; A substituted or unsubstituted adamantyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted pyridyl group; A substituted or unsubstituted carbazole group, or a direct bond with R1 or R2; Or bonded through a substituted or unsubstituted B, or adjacent groups are bonded to each other to form a substituted or unsubstituted phenanthrene ring; A substituted or unsubstituted indene ring; A substituted or unsubstituted cyclopentene ring; A substituted or unsubstituted cyclohexene ring; Or to form a substituted or unsubstituted benzofuran ring. The groups are substituted or unsubstituted with one or more groups selected from the group consisting of deuterium, a halogen group, an alkyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 20 carbon atoms, or a group to which two or more groups are bonded.

본 명세서의 일 실시상태에 따르면, R3 및 R5는 중수소, -F, 메틸기, CD3, i-프로필기, t-부틸기 및 페닐기로 이루어진 군에서 선택된 1 이상의 기 또는 2 이상의 기가 결합된 기로 치환 또는 비치환된다.According to an exemplary embodiment of the present specification, R3 and R5 are substituted with one or more groups selected from the group consisting of deuterium, -F, methyl group, CD 3 , i-propyl group, t-butyl group, and phenyl group, or a group to which two or more groups are bonded. Or unsubstituted.

본 명세서의 일 실시상태에 따르면, R3 및 R5는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 중수소, -F, 메틸기 및 페닐기로 이루어진 군에서 선택된 1 이상의 기 또는 2 이상이 연결된 기로 치환 또는 비치환된 메틸기; 중수소, -F, 메틸기 및 페닐기로 이루어진 군에서 선택된 1 이상의 기 또는 2 이상이 연결된 기로 치환 또는 비치환된 에틸기; 중수소, -F, 메틸기 및 페닐기로 이루어진 군에서 선택된 1 이상의 기 또는 2 이상이 연결된 기로 치환 또는 비치환된 프로필기; 중수소, -F, 메틸기 및 페닐기로 이루어진 군에서 선택된 1 이상의 기 또는 2 이상이 연결된 기로 치환 또는 비치환된 부틸기; 메틸기 또는 페닐기로 치환 또는 비치환된 실릴기; 중수소, 메틸기, CD3 또는 페닐기로 치환 또는 비치환된 붕소기; 중수소, 메틸기 또는 CD3로 치환 또는 비치환된 페닐프로필기; 중수소, 메틸기 또는 CD3로 치환 또는 비치환된 아다만틸기; 중수소, -F, 메틸기, 에틸기, 프로필기 및 부틸기로 이루어진 군에서 선택된 1 이상의 기 또는 2 이상이 연결된 기로 치환 또는 비치환된 페닐기; 중수소, 메틸기 또는 CD3로 치환 또는 비치환된 나프틸기; 중수소, 메틸기 또는 CD3로 치환 또는 비치환된 디벤조퓨란기; 중수소, 메틸기 또는 CD3로 치환 또는 비치환된 피리딜기; 또는 중수소, 메틸기 및 페닐기로 이루어진 군에서 선택된 1 이상의 기 또는 2 이상이 연결된 기로 치환 또는 비치환된 카바졸기이거나, R1 또는 R2와 직접결합; 또는 CD3로 치환 또는 비치환된 페닐기로 치환 또는 비치환된 B를 통하여 결합하거나, 인접하는 기는 서로 결합하여 중수소, 메틸기 또는 CD3로 치환 또는 비치환된 페난트렌 고리; 중수소, 메틸기 또는 CD3로 치환 또는 비치환된 인덴 고리; 중수소, 메틸기 또는 CD3로 치환 또는 비치환된 시클로펜텐 고리; 중수소, 메틸기 또는 CD3로 치환 또는 비치환된 시클로헥센 고리; 또는 중수소, 메틸기 또는 CD3로 치환 또는 비치환된 벤조퓨란 고리를 형성한다.According to an exemplary embodiment of the present specification, R3 and R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, -F, a methyl group and a phenyl group, or a group to which two or more are connected; An ethyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, -F, a methyl group and a phenyl group, or a group to which two or more are connected; A propyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, -F, a methyl group and a phenyl group, or a group to which two or more are connected; A butyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, -F, a methyl group and a phenyl group, or a group to which two or more are connected; A silyl group unsubstituted or substituted with a methyl group or a phenyl group; A boron group unsubstituted or substituted with deuterium, a methyl group, a CD 3 or a phenyl group; A phenylpropyl group unsubstituted or substituted with deuterium, a methyl group, or CD 3; An adamantyl group unsubstituted or substituted with deuterium, a methyl group, or CD 3; A phenyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, -F, a methyl group, an ethyl group, a propyl group, and a butyl group, or a group to which two or more are connected; A naphthyl group unsubstituted or substituted with deuterium, a methyl group, or CD 3; Dibenzofuran group unsubstituted or substituted with deuterium, methyl group or CD 3; A pyridyl group unsubstituted or substituted with deuterium, a methyl group, or CD 3; Or a carbazole group substituted or unsubstituted with one or more groups selected from the group consisting of deuterium, a methyl group and a phenyl group, or a group to which two or more are connected, or a direct bond with R1 or R2; Or a phenanthrene ring unsubstituted or substituted with deuterium, a methyl group, or a CD 3 by bonding through B unsubstituted or substituted with a phenyl group substituted or unsubstituted with CD 3, or adjacent groups are bonded to each other; Indene ring unsubstituted or substituted with deuterium, methyl group, or CD 3; A cyclopentene ring unsubstituted or substituted with deuterium, a methyl group, or CD 3; A cyclohexene ring unsubstituted or substituted with deuterium, a methyl group, or CD 3; Or a deuterium, methyl group, or CD 3 to form a substituted or unsubstituted benzofuran ring.

본 명세서의 일 실시상태에 따르면, R3 및 R5는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 중수소 또는 -F로 치환 또는 비치환된 메틸기; 중수소로 치환 또는 비치환된 에틸기; 중수소 및 페닐기로 이루어진 군에서 선택된 1 이상의 기 또는 2 이상이 연결된 기로 치환 또는 비치환된 i-프로필기; 중수소로 치환 또는 비치환된 t-부틸기; 트리메틸실릴기; 디페닐붕소기; 중수소로 치환 또는 비치환된 페닐프로필기; 아다만틸기; 중수소, -F, 중수소로 치환 또는 비치환된 메틸기 또는 중수소로 치환 또는 비치환된 i-프로필기로 치환 또는 비치환된 페닐기; 나프틸기; 디벤조퓨란기; 피리딜기; 또는 중수소, 중수소로 치환 또는 비치환된 메틸기 또는 CD3로 치환 또는 비치환된 페닐기로 치환 또는 비치환된 카바졸기이거나, R1 또는 R2와 직접결합; 또는 CD3로 치환 또는 비치환된 페닐기로 치환된 B를 통하여 결합하거나, 인접하는 기는 서로 결합하여 중수소, 메틸기 또는 CD3로 치환 또는 비치환된 페난트렌 고리; 중수소, 메틸기 또는 CD3로 치환 또는 비치환된 인덴 고리; 중수소, 메틸기 또는 CD3로 치환 또는 비치환된 시클로펜텐 고리; 중수소, 메틸기 또는 CD3로 치환 또는 비치환된 시클로헥센 고리; 또는 중수소, 메틸기 또는 CD3로 치환 또는 비치환된 벤조퓨란 고리를 형성한다.According to an exemplary embodiment of the present specification, R3 and R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium or -F; An ethyl group unsubstituted or substituted with deuterium; An i-propyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium and a phenyl group or a group to which two or more are connected; T-butyl group unsubstituted or substituted with deuterium; Trimethylsilyl group; Diphenylboron group; A phenylpropyl group unsubstituted or substituted with deuterium; Adamantyl group; Deuterium, -F, a methyl group unsubstituted or substituted with deuterium, or a phenyl group unsubstituted or substituted with an i-propyl group substituted or unsubstituted with deuterium; Naphthyl group; Dibenzofuran group; Pyridyl group; Or a carbazole group unsubstituted or substituted with deuterium, a methyl group unsubstituted or substituted with deuterium or a phenyl group unsubstituted or substituted with CD 3 , or a direct bond with R1 or R2; Or a phenanthrene ring unsubstituted or substituted with deuterium, a methyl group, or CD 3 by bonding through B substituted with a phenyl group substituted or unsubstituted with CD 3, or adjacent groups bonded to each other; Indene ring unsubstituted or substituted with deuterium, methyl group, or CD 3; A cyclopentene ring unsubstituted or substituted with deuterium, a methyl group, or CD 3; A cyclohexene ring unsubstituted or substituted with deuterium, a methyl group, or CD 3; Or a deuterium, methyl group, or CD 3 to form a substituted or unsubstituted benzofuran ring.

본 명세서의 일 실시상태에 따르면, R3 및 R5는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 중수소로 치환 또는 비치환된 메틸기; 중수소로 치환 또는 비치환된 에틸기; 중수소 및 페닐기로 이루어진 군에서 선택된 1 이상의 기 또는 2 이상이 연결된 기로 치환 또는 비치환된 i-프로필기; 중수소로 치환 또는 비치환된 t-부틸기; 중수소로 치환 또는 비치환된 페닐프로필기; 또는 중수소, 중수소로 치환 또는 비치환된 메틸기 또는 중수소로 치환 또는 비치환된 i-프로필기로 치환 또는 비치환된 페닐기이거나, R1 또는 R2와 직접결합; 또는 CD3로 치환 또는 비치환된 페닐기로 치환된 B를 통하여 결합하거나, 인접하는 기는 서로 결합하여 중수소, 메틸기 또는 CD3로 치환 또는 비치환된 인덴 고리; 중수소, 메틸기 또는 CD3로 치환 또는 비치환된 시클로헥센 고리; 또는 중수소, 메틸기 또는 CD3로 치환 또는 비치환된 벤조퓨란 고리를 형성한다.According to an exemplary embodiment of the present specification, R3 and R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium; An ethyl group unsubstituted or substituted with deuterium; An i-propyl group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium and a phenyl group or a group to which two or more are connected; T-butyl group unsubstituted or substituted with deuterium; A phenylpropyl group unsubstituted or substituted with deuterium; Or deuterium, a methyl group unsubstituted or substituted with deuterium, or a phenyl group unsubstituted or substituted with an i-propyl group substituted or unsubstituted with deuterium, or a direct bond with R1 or R2; Or an indene ring unsubstituted or substituted with deuterium, a methyl group, or CD 3 by bonding through B substituted with a phenyl group substituted or unsubstituted with CD 3, or adjacent groups bonded to each other; A cyclohexene ring unsubstituted or substituted with deuterium, a methyl group, or CD 3; Or a deuterium, methyl group, or CD 3 to form a substituted or unsubstituted benzofuran ring.

본 명세서의 일 실시상태에 따르면, 인접하는 R1 및 R3은 서로 결합하여 치환 또는 비치환된 고리를 형성한다.According to an exemplary embodiment of the present specification, adjacent R1 and R3 combine with each other to form a substituted or unsubstituted ring.

본 명세서의 일 실시상태에 따르면, 인접하는 R1 및 R3은 서로 결합하여 치환 또는 비치환된 카바졸 고리; 치환 또는 비치환된 헥사하이드로카바졸 고리; 또는 B를 통하여 연결되어 치환 또는 비치환된

Figure PCTKR2020012249-appb-I000033
고리를 형성한다.According to an exemplary embodiment of the present specification, adjacent R1 and R3 are bonded to each other to form a substituted or unsubstituted carbazole ring; Substituted or unsubstituted hexahydrocarbazole ring; Or substituted or unsubstituted by being linked through B
Figure PCTKR2020012249-appb-I000033
Form a ring

본 명세서의 일 실시상태에 따르면, 인접하는 R1 및 R3은 서로 결합하여 중수소; 또는 중수소로 치환된 탄소수 1 내지 3의 알킬기로 치환 또는 비치환된 카바졸 고리; 중수소; 또는 중수소로 치환된 탄소수 1 내지 3의 알킬기로 치환 또는 비치환된 헥사하이드로카바졸 고리; 또는 B를 통하여 연결되어 CD3로 치환된 페닐기로 치환 또는 비치환된

Figure PCTKR2020012249-appb-I000034
고리를 형성한다.According to an exemplary embodiment of the present specification, adjacent R1 and R3 are combined with each other to deuterium; Or a carbazole ring unsubstituted or substituted with an alkyl group having 1 to 3 carbon atoms substituted with deuterium; heavy hydrogen; Or a hexahydrocarbazole ring unsubstituted or substituted with an alkyl group having 1 to 3 carbon atoms substituted with deuterium; Or substituted or unsubstituted with a phenyl group linked through B and substituted with CD 3
Figure PCTKR2020012249-appb-I000034
Form a ring

본 명세서의 일 실시상태에 따르면, 인접하는 R1 및 R3은 서로 결합하여 CD3로 치환 또는 비치환된 헥사하이드로카바졸 고리를 형성한다.According to an exemplary embodiment of the present specification, adjacent R1 and R3 combine with each other to form a hexahydrocarbazole ring substituted or unsubstituted with CD 3.

본 명세서의 일 실시상태에 따르면, 인접하는 R2 및 R5은 서로 결합하여 치환 또는 비치환된 고리를 형성한다.According to an exemplary embodiment of the present specification, adjacent R2 and R5 combine with each other to form a substituted or unsubstituted ring.

본 명세서의 일 실시상태에 따르면, 인접하는 R2 및 R5은 서로 결합하여 치환 또는 비치환된 카바졸 고리; 치환 또는 비치환된 헥사하이드로카바졸 고리; 또는 B를 통하여 연결되어 치환 또는 비치환된

Figure PCTKR2020012249-appb-I000035
고리를 형성한다.According to an exemplary embodiment of the present specification, adjacent R2 and R5 are bonded to each other to form a substituted or unsubstituted carbazole ring; Substituted or unsubstituted hexahydrocarbazole ring; Or substituted or unsubstituted by being linked through B
Figure PCTKR2020012249-appb-I000035
Form a ring

본 명세서의 일 실시상태에 따르면, 인접하는 R2 및 R5은 서로 결합하여 중수소; 또는 중수소로 치환된 탄소수 1 내지 3의 알킬기로 치환 또는 비치환된 카바졸 고리; 중수소; 또는 중수소로 치환된 탄소수 1 내지 3의 알킬기로 치환 또는 비치환된 헥사하이드로카바졸 고리; 또는 B를 통하여 연결되어 CD3로 치환된 페닐기로 치환 또는 비치환된

Figure PCTKR2020012249-appb-I000036
고리를 형성한다.According to an exemplary embodiment of the present specification, adjacent R2 and R5 are combined with each other to deuterium; Or a carbazole ring unsubstituted or substituted with an alkyl group having 1 to 3 carbon atoms substituted with deuterium; heavy hydrogen; Or a hexahydrocarbazole ring unsubstituted or substituted with an alkyl group having 1 to 3 carbon atoms substituted with deuterium; Or substituted or unsubstituted with a phenyl group linked through B and substituted with CD 3
Figure PCTKR2020012249-appb-I000036
Form a ring

본 명세서의 일 실시상태에 따르면, 인접하는 R2 및 R5은 서로 결합하여 CD3로 치환 또는 비치환된 헥사하이드로카바졸 고리를 형성한다.According to an exemplary embodiment of the present specification, adjacent R2 and R5 combine with each other to form a hexahydrocarbazole ring substituted or unsubstituted with CD 3.

본 명세서의 일 실시상태에 따르면, 상기 R1 내지 R5는 -L-R11로 표시되고,According to an exemplary embodiment of the present specification, R1 to R5 are represented by -L-R11,

L은 직접결합; O; S; SO2; 치환 또는 비치환된 알킬렌기; 또는 치환 또는 비치환된 아릴렌기이고,L is a direct bond; O; S; SO 2 ; A substituted or unsubstituted alkylene group; Or a substituted or unsubstituted arylene group,

R11은 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 할로알킬기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이다.R11 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

본 명세서의 일 실시상태에 따르면, L은 직접결합; O; S; SO2; 치환 또는 비치환된 탄소수 1 내지 20의 알킬렌기; 또는 치환 또는 비치환된 탄소수 6 내지 20의 아릴렌기이다.According to an exemplary embodiment of the present specification, L is a direct bond; O; S; SO 2 ; A substituted or unsubstituted C 1 to C 20 alkylene group; Or a substituted or unsubstituted C6 to C20 arylene group.

본 명세서의 일 실시상태에 따르면, L은 직접결합; O; S; SO2; 치환 또는 비치환된 탄소수 1 내지 10의 알킬렌기; 또는 치환 또는 비치환된 탄소수 6 내지 10의 아릴렌기이다.According to an exemplary embodiment of the present specification, L is a direct bond; O; S; SO 2 ; A substituted or unsubstituted C1-C10 alkylene group; Or a substituted or unsubstituted C6 to C10 arylene group.

본 명세서의 일 실시상태에 따르면, L은 직접결합; O; S; SO2; 또는 치환 또는 비치환된 탄소수 1 내지 5의 알킬렌기이다.According to an exemplary embodiment of the present specification, L is a direct bond; O; S; SO 2 ; Or a substituted or unsubstituted C 1 to C 5 alkylene group.

본 명세서의 일 실시상태에 따르면, L은 직접결합; O; S; SO2; 치환 또는 비치환된 메틸렌기; 또는 치환 또는 비치환된 메틸렌기 프로필렌기이다.According to an exemplary embodiment of the present specification, L is a direct bond; O; S; SO 2 ; A substituted or unsubstituted methylene group; Or a substituted or unsubstituted methylene group is a propylene group.

본 명세서의 일 실시상태에 따르면, L은 직접결합; O; S; SO2; CD3로 치환 또는 비치환된 메틸렌기; 또는 중수소로 치환 또는 비치환된 프로필렌기이다.According to an exemplary embodiment of the present specification, L is a direct bond; O; S; SO 2 ; A methylene group unsubstituted or substituted with CD 3; Or a propylene group unsubstituted or substituted with deuterium.

본 명세서의 일 실시상태에 따르면, L은 직접결합; O; CD3로 치환 또는 비치환된 메틸렌기; 또는 중수소로 치환 또는 비치환된 프로필렌기이다.According to an exemplary embodiment of the present specification, L is a direct bond; O; A methylene group unsubstituted or substituted with CD 3; Or a propylene group unsubstituted or substituted with deuterium.

본 명세서의 일 실시상태에 따르면, R11은 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 할로알킬기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이다.[0366] According to an exemplary embodiment of the present specification, R11 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted haloalkyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

본 명세서의 일 실시상태에 따르면, R11은 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 20의 알킬기; 치환 또는 비치환된 탄소수 1 내지 20의 할로알킬기; 치환 또는 비치환된 탄소수 1 내지 20의 아민기; 치환 또는 비치환된 탄소수 6 내지 20의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 20의 헤테로고리기이다.[0366] According to an exemplary embodiment of the present specification, R11 is hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted C1 to C20 haloalkyl group; A substituted or unsubstituted amine group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted C2 to C20 heterocyclic group.

본 명세서의 일 실시상태에 따르면, R11은 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 10의 알킬기; 치환 또는 비치환된 탄소수 1 내지 10의 할로알킬기; 치환 또는 비치환된 탄소수 1 내지 15의 아민기; 치환 또는 비치환된 탄소수 6 내지 10의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 10의 헤테로고리기이다.[0366] According to an exemplary embodiment of the present specification, R11 is hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted haloalkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted amine group having 1 to 15 carbon atoms; A substituted or unsubstituted aryl group having 6 to 10 carbon atoms; Or a substituted or unsubstituted C2 to C10 heterocyclic group.

본 명세서의 일 실시상태에 따르면, R11은 수소; 중수소; CD3; CF3; 또는 중수소 또는 CD3로 치환 또는 비치환된 페닐기이다.[0366] According to an exemplary embodiment of the present specification, R11 is hydrogen; heavy hydrogen; CD 3 ; CF 3 ; Or a phenyl group unsubstituted or substituted with deuterium or CD 3.

본 명세서의 일 실시상태에 따르면, R11은 수소; 중수소; CD3; 또는 중수소 또는 CD3로 치환 또는 비치환된 페닐기이다.[0366] According to an exemplary embodiment of the present specification, R11 is hydrogen; heavy hydrogen; CD 3 ; Or a phenyl group unsubstituted or substituted with deuterium or CD 3.

본 명세서의 일 실시상태에 따르면, R1 또는 R2는 인접하는 기와 서로 결합하여 치환 또는 비치환된 지방족 탄화수소고리; 치환 또는 비치환된 방향족 탄화수소고리; 치환 또는 비치환된 방향족 헤테로고리; 또는 치환 또는 비치환된 지방족 탄화수소고리 및 방향족 탄화수소고리의 축합고리를 형성한다.According to an exemplary embodiment of the present specification, R1 or R2 is a substituted or unsubstituted aliphatic hydrocarbon ring bonded to each other with adjacent groups; A substituted or unsubstituted aromatic hydrocarbon ring; Substituted or unsubstituted aromatic heterocycle; Or it forms a condensed ring of a substituted or unsubstituted aliphatic hydrocarbon ring and an aromatic hydrocarbon ring.

본 명세서의 일 실시상태에 따르면, R1 또는 R2는 인접하는 기와 서로 결합하여 치환 또는 비치환된 단환 내지 4환의 지방족 탄화수소고리; 치환 또는 비치환된 단환 내지 4환의 방향족 탄화수소고리; 치환 또는 비치환된 단환 내지 4환의 방향족 헤테로고리; 또는 치환 또는 비치환된 단환 내지 4환의 지방족 탄화수소고리 및 단환 내지 4환의 방향족 탄화수소고리의 축합고리를 형성한다.According to an exemplary embodiment of the present specification, R1 or R2 is a substituted or unsubstituted monocyclic to tetracyclic aliphatic hydrocarbon ring by bonding with an adjacent group to each other; Substituted or unsubstituted mono- to 4-cyclic aromatic hydrocarbon rings; A substituted or unsubstituted monocyclic to 4 ring aromatic heterocycle; Or a substituted or unsubstituted monocyclic to 4 ring aliphatic hydrocarbon ring and a monocyclic to 4 ring aromatic hydrocarbon ring to form a condensed ring.

본 명세서의 일 실시상태에 따르면, R1 또는 R2는 인접하는 기와 서로 결합하여 치환 또는 비치환된 단환의 지방족 탄화수소고리; 치환 또는 비치환된 단환 내지 4환의 방향족 탄화수소고리; 치환 또는 비치환된 단환 내지 3환의 방향족 헤테로고리; 또는 치환 또는 비치환된 단환 또는 2환의 지방족 탄화수소고리 및 단환 또는 2환의 방향족 탄화수소고리의 축합고리를 형성한다.According to an exemplary embodiment of the present specification, R1 or R2 is a substituted or unsubstituted monocyclic aliphatic hydrocarbon ring by bonding to each other with adjacent groups; Substituted or unsubstituted mono- to 4-cyclic aromatic hydrocarbon rings; A substituted or unsubstituted monocyclic to tricyclic aromatic heterocycle; Or a condensed ring of a substituted or unsubstituted monocyclic or bicyclic aliphatic hydrocarbon ring and a monocyclic or bicyclic aromatic hydrocarbon ring.

본 명세서의 일 실시상태에 따르면, R1 또는 R2는 인접하는 기와 서로 결합하여 치환 또는 비치환된 탄소수 3 내지 30의 지방족 탄화수소고리; 치환 또는 비치환된 탄소수 6 내지 30의 방향족 탄화수소고리; 치환 또는 비치환된 탄소수 2 내지 30의 방향족 헤테로고리; 또는 치환 또는 비치환된 탄소수 3 내지 30의 지방족 탄화수소고리 및 탄소수 6 내지 30의 방향족 탄화수소고리의 축합고리를 형성한다.According to an exemplary embodiment of the present specification, R1 or R2 is a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms by bonding with an adjacent group; A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms; A substituted or unsubstituted C2 to C30 aromatic heterocycle; Alternatively, a condensed ring of a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms and an aromatic hydrocarbon ring having 6 to 30 carbon atoms is formed.

본 명세서의 일 실시상태에 따르면, R1 또는 R2는 인접하는 기와 서로 결합하여 치환 또는 비치환된 탄소수 3 내지 20의 지방족 탄화수소고리; 치환 또는 비치환된 탄소수 6 내지 20의 방향족 탄화수소고리; 치환 또는 비치환된 탄소수 2 내지 20의 방향족 헤테로고리; 또는 치환 또는 비치환된 탄소수 3 내지 20의 지방족 탄화수소고리 및 탄소수 6 내지 20의 방향족 탄화수소고리의 축합고리를 형성한다.According to an exemplary embodiment of the present specification, R1 or R2 is a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 carbon atoms by bonding with an adjacent group; A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 20 carbon atoms; A substituted or unsubstituted C2 to C20 aromatic heterocycle; Alternatively, a condensed ring of a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 carbon atoms and an aromatic hydrocarbon ring having 6 to 20 carbon atoms is formed.

본 명세서의 일 실시상태에 따르면, R1 또는 R2는 각각 R3 또는 R5와 직접결합하거나, 치환 또는 비치환된 페닐기로 치환된 B를 통하여 결합하거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 페난트렌 고리; 치환 또는 비치환된 인덴 고리; 치환 또는 비치환된 벤조퓨란 고리; 치환 또는 비치환된 벤조티오펜 고리; 치환 또는 비치환된 인돌 고리; 치환 또는 비치환된 카바졸 고리; 치환 또는 비치환된 시클로펜텐 고리; 치환 또는 비치환된 시클로헥센 고리; 치환 또는 비치환된 시클로헵텐 고리; 치환 또는 비치환된 테트라하이드로나프탈렌 고리; 치환 또는 비치환된 다이하이드로벤조다이옥신(dihydrobenzo[b]dioxine)고리; 치환 또는 비치환된 테트라하이드로에타노나프탈렌(tetrahydroethanonaphthalene) 고리; 치환 또는 비치환된 바이사이클로헵텐 고리; 치환 또는 비치환된 바이사이클로옥텐 고리; 또는 치환 또는 비치환된 헥사하이드로카바졸기를 형성한다. 상기 기들은 중수소, 할로겐기, 탄소수 1 내지 10의 알킬기 및 탄소수 6 내지 20의 아릴기로 이루어진 군에서 선택된 1 이상의 기 또는 2 이상의 기가 결합된 기로 치환 또는 비치환된다.According to an exemplary embodiment of the present specification, R1 or R2 is each directly bonded to R3 or R5, bonded through B substituted with a substituted or unsubstituted phenyl group, or bonded to an adjacent group through a substituted or unsubstituted phenanthrene. ring; A substituted or unsubstituted indene ring; A substituted or unsubstituted benzofuran ring; Substituted or unsubstituted benzothiophene ring; A substituted or unsubstituted indole ring; Substituted or unsubstituted carbazole ring; A substituted or unsubstituted cyclopentene ring; A substituted or unsubstituted cyclohexene ring; A substituted or unsubstituted cycloheptene ring; A substituted or unsubstituted tetrahydronaphthalene ring; A substituted or unsubstituted dihydrobenzo[b]dioxine ring; A substituted or unsubstituted tetrahydroethanonaphthalene ring; A substituted or unsubstituted bicycloheptene ring; A substituted or unsubstituted bicyclooctene ring; Or a substituted or unsubstituted hexahydrocarbazole group is formed. The groups are substituted or unsubstituted with one or more groups selected from the group consisting of deuterium, a halogen group, an alkyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 20 carbon atoms, or a group to which two or more groups are bonded.

본 명세서의 일 실시상태에 따르면, R1 또는 R2는 각각 R3 또는 R5와 직접결합하거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 인덴 고리; 치환 또는 비치환된 벤조퓨란 고리; 치환 또는 비치환된 벤조티오펜 고리; 치환 또는 비치환된 시클로펜텐 고리; 치환 또는 비치환된 시클로헥센 고리; 또는 치환 또는 비치환된 테트라하이드로에타노나프탈렌(tetrahydroethanonaphthalene) 고리를 형성한다. 상기 기들은 중수소, 메틸기, 에틸기, 프로필기, 부틸기 및 페닐기로 이루어진 군에서 선택된 1 이상의 기 또는 2 이상의 기가 결합된 기로 치환 또는 비치환된다.According to an exemplary embodiment of the present specification, R1 or R2 is directly bonded to R3 or R5, respectively, or by bonding with an adjacent group to each other to form a substituted or unsubstituted indene ring; A substituted or unsubstituted benzofuran ring; Substituted or unsubstituted benzothiophene ring; A substituted or unsubstituted cyclopentene ring; A substituted or unsubstituted cyclohexene ring; Or a substituted or unsubstituted tetrahydroethanonaphthalene ring is formed. The groups are substituted or unsubstituted with one or more groups selected from the group consisting of deuterium, methyl group, ethyl group, propyl group, butyl group, and phenyl group, or a group to which two or more groups are bonded.

본 명세서의 일 실시상태에 따르면, R1 또는 R2가 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성하는 경우는 R1 또는 R2가 각각 R3 또는 R5와 직접결합하여 카바졸 고리; 또는 헥사하이드로카바졸 고리를 이루거나, B를 통하여 연결되어

Figure PCTKR2020012249-appb-I000037
고리를 이루는 경우를 포함한다. 상기 고리들은 치환 또는 비치환된다.According to an exemplary embodiment of the present specification, when R1 or R2 is bonded to an adjacent group to form a substituted or unsubstituted ring, R1 or R2 is directly bonded to R3 or R5 to form a carbazole ring; Or it forms a hexahydrocarbazole ring, or is connected through B
Figure PCTKR2020012249-appb-I000037
Includes the case of forming a ring. The rings are substituted or unsubstituted.

본 명세서의 일 실시상태에 따르면, R1 또는 R2가 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성하는 경우, 상기 고리는 하기 화학식 C1 내지 C3 중 어느 하나로 표시된다.According to an exemplary embodiment of the present specification, when R1 or R2 combines with an adjacent group to form a substituted or unsubstituted ring, the ring is represented by any one of the following formulas C1 to C3.

[화학식 C1]　　　　[화학식 C2]　　　[화학식 C3][Chemical Formula C1]　　　　[Chemical Formula C2]　　　[Chemical Formula C3]

Figure PCTKR2020012249-appb-I000038
Figure PCTKR2020012249-appb-I000038

상기 화학식 C1 내지 C3에 있어서,In the above formulas C1 to C3,

X21, X22 및 X31은 서로 동일하거나 상이하고, 각각 독립적으로, O; S; CP11P12; 또는 NP13이고,X21, X22 and X31 are the same as or different from each other, and each independently O; S; CP11P12; Or NP13,

P1 및 P11 내지 P13은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성하고,P1 and P11 to P13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combined with an adjacent group to form a substituted or unsubstituted ring,

b1은 1 내지 3의 정수이고,b1 is an integer of 1 to 3,

p1은 0 내지 10의 정수이고, p2 및 p3는 각각 0 내지 4의 정수이고,p1 is an integer of 0 to 10, p2 and p3 are each an integer of 0 to 4,

p1 내지 p3가 각각 2 이상인 경우, 2 이상의 P1은 서로 동일하거나 상이하고,When p1 to p3 are each 2 or more, 2 or more P1s are the same as or different from each other,

*는 형성된 고리가 축합되는 위치를 의미한다.* Means the position where the formed ring is condensed.

본 명세서의 일 실시상태에 따르면, X21 및 X22은 서로 동일하거나 상이하고, 각각 독립적으로, O; S; 또는 CP11P12이다.According to an exemplary embodiment of the present specification, X21 and X22 are the same as or different from each other, and each independently, O; S; Or CP11P12.

본 명세서의 일 실시상태에 따르면, X31은 O; S; CP11P12; 또는 NP13이다.According to an exemplary embodiment of the present specification, X31 is O; S; CP11P12; Or NP13.

본 명세서의 일 실시상태에 따르면, P1 및 P11 내지 P13은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 30의 알킬기; 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 헤테로고리기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 30의 방향족 탄화수소고리; 또는 치환 또는 비치환된 탄소수 3 내지 30의 지방족 탄화수소고리를 형성한다.According to an exemplary embodiment of the present specification, P1 and P11 to P13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C30 alkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms by bonding with an adjacent group; Or a substituted or unsubstituted C 3 to C 30 aliphatic hydrocarbon ring is formed.

본 명세서의 일 실시상태에 따르면, P1 및 P11 내지 P13은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 20의 알킬기; 치환 또는 비치환된 탄소수 6 내지 20의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 20의 헤테로고리기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 20의 방향족 탄화수소고리; 또는 치환 또는 비치환된 탄소수 3 내지 20의 지방족 탄화수소고리를 형성한다.According to an exemplary embodiment of the present specification, P1 and P11 to P13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 20 carbon atoms by bonding with an adjacent group; Or a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 carbon atoms.

본 명세서의 일 실시상태에 따르면, P1 및 P11 내지 P13은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 중수소로 치환 또는 비치환된 알킬기; 페닐기이거나, 인접한 기와 서로 결합하여 중수소 또는 중수소로 치환 또는 비치환된 알킬기로 치환 또는 비치환된 벤젠고리를 형성하거나, 바이시클로헵탄고리 또는 바이시클로옥탄고리를 이룬다.According to an exemplary embodiment of the present specification, P1 and P11 to P13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; An alkyl group unsubstituted or substituted with deuterium; It is a phenyl group, or combines with an adjacent group to form a benzene ring substituted or unsubstituted with an alkyl group substituted or unsubstituted with deuterium or deuterium, or a bicycloheptane ring or a bicyclooctane ring.

본 명세서의 일 실시상태에 따르면, P1 및 P11 내지 P13은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 중수소로 치환 또는 비치환된 메틸기; 중수소로 치환 또는 비치환된 에틸기; 중수소로 치환 또는 비치환된 프로필기; 중수소로 치환 또는 비치환된 부틸기; 또는 페닐기이거나, 인접한 기와 서로 결합하여 중수소 또는 중수소로 치환 또는 비치환된 메틸기로 치환 또는 비치환된 벤젠고리를 형성하거나, 바이시클로헵탄고리 또는 바이시클로옥탄고리를 이룬다.According to an exemplary embodiment of the present specification, P1 and P11 to P13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium; An ethyl group unsubstituted or substituted with deuterium; A propyl group unsubstituted or substituted with deuterium; A butyl group unsubstituted or substituted with deuterium; Or a phenyl group, or a benzene ring unsubstituted or substituted with a methyl group unsubstituted or substituted with deuterium or deuterium by bonding to each other with an adjacent group, or a bicycloheptane ring or a bicyclooctane ring.

본 명세서의 일 실시상태에 따르면, b1은 1 또는 2이다.According to an exemplary embodiment of the present specification, b1 is 1 or 2.

본 명세서의 일 실시상태에 따르면, p1은 1 내지 6의 정수이다.According to an exemplary embodiment of the present specification, p1 is an integer of 1 to 6.

본 명세서의 일 실시상태에 따르면, p1은 1 내지 4의 정수이다.According to an exemplary embodiment of the present specification, p1 is an integer of 1 to 4.

본 명세서의 일 실시상태에 따르면, p2 및 p3는 1 내지 4의 정수이다.According to an exemplary embodiment of the present specification, p2 and p3 are integers of 1 to 4.

본 명세서의 일 실시상태에 따르면, R1 또는 R2가 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성하는 경우, 하기 구조들 중 어느 하나로 표시된다.According to an exemplary embodiment of the present specification, when R1 or R2 combines with an adjacent group to form a substituted or unsubstituted ring, it is represented by one of the following structures.

Figure PCTKR2020012249-appb-I000039
Figure PCTKR2020012249-appb-I000039

상기 구조들에 있어서, *는 형성된 고리가 축합되는 위치를 의미하고, 상기 구조들은 중수소; 또는 중수소로 치환 또는 비치환된 알킬기로 치환 또는 비치환된다.In the above structures, * means a position at which the formed ring is condensed, and the structures include deuterium; Or it is unsubstituted or substituted with a deuterium-substituted or unsubstituted alkyl group.

본 명세서의 일 실시상태에 따르면, 상기 구조들은 중수소; 또는 중수소로 치환 또는 비치환된 메틸기; 중수소로 치환 또는 비치환된 에틸기; 중수소로 치환 또는 비치환된 프로필기; 또는 중수소로 치환 또는 비치환된 부틸기로 치환 또는 비치환된다.According to an exemplary embodiment of the present specification, the structures are deuterium; Or a methyl group unsubstituted or substituted with deuterium; An ethyl group unsubstituted or substituted with deuterium; A propyl group unsubstituted or substituted with deuterium; Or substituted or unsubstituted with deuterium substituted or unsubstituted butyl group.

본 명세서의 일 실시상태에 따르면, 상기 구조들은 중수소; 또는 중수소로 치환 또는 비치환된 메틸기; 중수소로 치환 또는 비치환된 에틸기; 중수소로 치환 또는 비치환된 i-프로필기; 또는 중수소로 치환 또는 비치환된 t-부틸기로 치환 또는 비치환된다.According to an exemplary embodiment of the present specification, the structures are deuterium; Or a methyl group unsubstituted or substituted with deuterium; An ethyl group unsubstituted or substituted with deuterium; I-propyl group unsubstituted or substituted with deuterium; Or it is unsubstituted or substituted with a t-butyl group substituted or unsubstituted with deuterium.

본 명세서의 일 실시상태에 따르면, 상기 구조들은 중수소; 또는 CD3 로 치환 또는 비치환된다.According to an exemplary embodiment of the present specification, the structures are deuterium; Or it is substituted or unsubstituted with CD 3.

본 명세서의 일 실시상태에 따르면, Y가 중수소로 치환된 탄소수 1 내지 3의 알킬기인 경우, X1, X2 및 R1 내지 R5 중 적어도 하나는 중수소로 치환된 탄소수 1 내지 3의 알킬기이다.According to an exemplary embodiment of the present specification, when Y is an alkyl group having 1 to 3 carbon atoms substituted with deuterium, at least one of X1, X2 and R1 to R5 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium.

본 명세서의 일 실시상태에 따르면, Y가 중수소로 치환된 탄소수 1 내지 3의 알킬기인 경우, R1 내지 R5 중 적어도 하나는 중수소로 치환된 탄소수 1 내지 3의 알킬기이다.According to an exemplary embodiment of the present specification, when Y is an alkyl group having 1 to 3 carbon atoms substituted with deuterium, at least one of R1 to R5 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium.

본 명세서의 일 실시상태에 따르면, X1, X2 및 R1 내지 R5 중 적어도 2개는 중수소로 치환된 탄소수 1 내지 3의 알킬기이다.According to an exemplary embodiment of the present specification, at least two of X1, X2, and R1 to R5 are an alkyl group having 1 to 3 carbon atoms substituted with deuterium.

본 명세서의 일 실시상태에 따르면, X1, X2 및 R1 내지 R5 중 적어도 3개는 중수소로 치환된 탄소수 1 내지 3의 알킬기이다.According to an exemplary embodiment of the present specification, at least three of X1, X2, and R1 to R5 are an alkyl group having 1 to 3 carbon atoms substituted with deuterium.

본 명세서의 일 실시상태에 따르면, X1, X2 및 R1 내지 R5 중 적어도 하나는 중수소로 치환된 메틸기; 중수소로 치환된 에틸기; 또는 중수소로 치환된 프로필기 중 선택된다.According to an exemplary embodiment of the present specification, at least one of X1, X2, and R1 to R5 is a methyl group substituted with deuterium; An ethyl group substituted with deuterium; Or it is selected from a propyl group substituted with deuterium.

본 명세서의 일 실시상태에 따르면, X1, X2 및 R1 내지 R5 중 적어도 하나는 중수소로 치환된 메틸기; 중수소로 치환된 에틸기; 또는 중수소로 치환된 i-프로필기 중 선택된다.According to an exemplary embodiment of the present specification, at least one of X1, X2, and R1 to R5 is a methyl group substituted with deuterium; An ethyl group substituted with deuterium; Or it is selected from i-propyl group substituted with deuterium.

본 명세서의 일 실시상태에 따르면, X1, X2 및 R1 내지 R5 중 적어도 2개는 중수소로 치환된 메틸기; 중수소로 치환된 에틸기; 또는 중수소로 치환된 i-프로필기 중 선택된다.According to an exemplary embodiment of the present specification, at least two of X1, X2, and R1 to R5 are methyl groups substituted with deuterium; An ethyl group substituted with deuterium; Or it is selected from i-propyl group substituted with deuterium.

본 명세서의 일 실시상태에 따르면, X1, X2 및 R1 내지 R5 중 적어도 3개는 중수소로 치환된 메틸기; 중수소로 치환된 에틸기; 또는 중수소로 치환된 i-프로필기 중 선택된다.According to an exemplary embodiment of the present specification, at least three of X1, X2, and R1 to R5 are methyl groups substituted with deuterium; An ethyl group substituted with deuterium; Or it is selected from i-propyl group substituted with deuterium.

본 명세서의 일 실시상태에 따르면, 상기 R1 내지 R5 중 적어도 2개는 중수소로 치환된 탄소수 1 내지 3의 알킬기이다.According to an exemplary embodiment of the present specification, at least two of R1 to R5 are an alkyl group having 1 to 3 carbon atoms substituted with deuterium.

본 명세서의 일 실시상태에 따르면, 상기 R1 내지 R5 중 적어도 3개는 중수소로 치환된 탄소수 1 내지 3의 알킬기이다.According to an exemplary embodiment of the present specification, at least three of R1 to R5 are an alkyl group having 1 to 3 carbon atoms substituted with deuterium.

본 명세서의 일 실시상태에 따르면, R1 내지 R5 중 적어도 하나는 -CD3; -C2D5; CH2CD3; CD(CD3)2 또는 CH(CD3)2 중 선택된다.According to an exemplary embodiment of the present specification, at least one of R1 to R5 is -CD 3 ; -C 2 D 5 ; CH 2 CD 3 ; It is selected from CD(CD 3 ) 2 or CH(CD 3 ) 2 .

본 명세서의 일 실시상태에 따르면, R1 내지 R5 중 적어도 2개는 -CD3; -C2D5; CH2CD3; CD(CD3)2 또는 CH(CD3)2 중 선택된다.According to an exemplary embodiment of the present specification, at least two of R1 to R5 are -CD 3 ; -C 2 D 5 ; CH 2 CD 3 ; It is selected from CD(CD 3 ) 2 or CH(CD 3 ) 2 .

본 명세서의 일 실시상태에 따르면, R1 내지 R5 중 적어도 3개는 -CD3; -C2D5; CH2CD3; CD(CD3)2 또는 CH(CD3)2 중 선택된다.According to an exemplary embodiment of the present specification, at least three of R1 to R5 are -CD 3 ; -C 2 D 5 ; CH 2 CD 3 ; It is selected from CD(CD 3 ) 2 or CH(CD 3 ) 2 .

본 명세서의 일 실시상태에 따르면, R1 내지 R5 중 적어도 하나는 CD3이다.According to an exemplary embodiment of the present specification, at least one of R1 to R5 is CD 3 .

본 명세서의 일 실시상태에 따르면, R1 내지 R5 중 적어도 2개는 CD3이다.According to an exemplary embodiment of the present specification, at least two of R1 to R5 are CD 3 .

본 명세서의 일 실시상태에 따르면, R1 내지 R5 중 적어도 3개는 CD3이다.According to an exemplary embodiment of the present specification, at least three of R1 to R5 are CD 3 .

본 명세서의 일 실시상태에 따르면, R4는 서로 동일하거나 상이하고, 각각 독립적으로 수소 또는 CD---3이다.According to an exemplary embodiment of the present disclosure, R4 are the same or different and each is independently hydrogen or CD from each other - is 3 -

본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 101로 표시될 수 있다.According to an exemplary embodiment of the present specification, Chemical Formula 1 may be represented by Chemical Formula 101 below.

[화학식 101][Formula 101]

Figure PCTKR2020012249-appb-I000040
Figure PCTKR2020012249-appb-I000040

상기 화학식 101에 있어서, 치환기들의 정의는 화학식 1에서의 정의와 같다.In Chemical Formula 101, the definitions of the substituents are the same as those in Chemical Formula 1.

본 명세서의 일 실시상태에 따르면, Y는 중수소로 치환된 탄소수 1 내지 3의 알킬기; 또는 하기 화학식 2로 표시된다.According to an exemplary embodiment of the present specification, Y is an alkyl group having 1 to 3 carbon atoms substituted with deuterium; Or it is represented by the following formula 2.

본 명세서의 일 실시상태에 따르면, Y는 중수소로 치환된 메틸기; 중수소로 치환된 에틸기; 또는 중수소로 치환된 프로필기이다.According to an exemplary embodiment of the present specification, Y is a methyl group substituted with deuterium; An ethyl group substituted with deuterium; Or it is a propyl group substituted with deuterium.

본 명세서의 일 실시상태에 따르면, Y는 중수소로 치환된 메틸기; 중수소로 치환된 에틸기; 또는 중수소로 치환된 i-프로필기이다.According to an exemplary embodiment of the present specification, Y is a methyl group substituted with deuterium; An ethyl group substituted with deuterium; Or an i-propyl group substituted with deuterium.

본 명세서의 일 실시상태에 따르면, Y는 CDH2; CD2H; CD3; C2D5; CH2CD3; CD(CD3)2; 또는 CH(CD3)2이다.According to an exemplary embodiment of the present specification, Y is CDH 2 ; CD 2 H; CD 3 ; C 2 D 5 ; CH 2 CD 3 ; CD(CD 3 ) 2 ; Or CH(CD 3 ) 2 .

본 명세서의 일 실시상태에 따르면, Y는 -CD3; -C2D5; CH2CD3; CD(CD3)2 또는 CH(CD3)2이다.According to an exemplary embodiment of the present specification, Y is -CD 3 ; -C 2 D 5 ; CH 2 CD 3 ; It is either CD(CD 3 ) 2 or CH(CD 3 ) 2 .

본 명세서의 일 실시상태에 따르면, Y는 CDH2; CD2H 또는 CD3이다.According to an exemplary embodiment of the present specification, Y is CDH 2 ; It is either CD 2 H or CD 3.

본 명세서의 일 실시상태에 따르면, Y는 CD3이다.According to an exemplary embodiment of the present specification, Y is CD 3 .

본 명세서의 일 실시상태에 따르면, Y는 하기 화학식 2로 표시된다.According to an exemplary embodiment of the present specification, Y is represented by the following formula (2).

[화학식 2][Formula 2]

Figure PCTKR2020012249-appb-I000041
Figure PCTKR2020012249-appb-I000041

상기 화학식 2에 있어서,In Formula 2,

B1 및 B2는 서로 동일하거나 상이하고, 각각 독립적으로 지방족 탄화수소 고리; 또는 방향족 탄화수소 고리이고,B1 and B2 are the same as or different from each other, and each independently an aliphatic hydrocarbon ring; Or an aromatic hydrocarbon ring,

R6 및 R7은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 알키닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 아릴알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 인접하는 기는 서로 결합하여 치환 또는 비치환된 고리를 형성하고,R6 and R7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkyl thioxy group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,

r6 및 r7는 서로 동일하거나 상이하고, 각각 독립적으로 1 내지 11의 정수이고, r6 및 r7이 각각 2 이상인 경우, 각각의 괄호 안의 치환기는 서로 동일하거나 상이하고,r6 and r7 are the same as or different from each other, and each independently an integer of 1 to 11, and when r6 and r7 are each 2 or more, the substituents in each parenthesis are the same or different from each other,

Figure PCTKR2020012249-appb-I000042
는 화학식 1에 결합되는 위치를 의미한다.
Figure PCTKR2020012249-appb-I000042
Means a position bonded to the formula (1).

본 명세서의 일 실시상태에 따르면, B1 및 B2는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 3 내지 30의 지방족 탄화수소 고리; 또는 치환 또는 비치환된 탄소수 6 내지 30의 방향족 탄화수소 고리이다.According to an exemplary embodiment of the present specification, B1 and B2 are the same as or different from each other, and each independently a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 30 carbon atoms; Or a substituted or unsubstituted C6-C30 aromatic hydrocarbon ring.

본 명세서의 일 실시상태에 따르면, B1 및 B2는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 3 내지 20의 지방족 탄화수소 고리; 또는 치환 또는 비치환된 탄소수 6 내지 20의 방향족 탄화수소 고리이다.According to an exemplary embodiment of the present specification, B1 and B2 are the same as or different from each other, and each independently a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 carbon atoms; Or a substituted or unsubstituted C 6 to C 20 aromatic hydrocarbon ring.

본 명세서의 일 실시상태에 따르면, B1 및 B2는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 단환 내지 3환의 지방족 탄화수소 고리; 또는 치환 또는 비치환된 단환 내지 3환의 방향족 탄화수소 고리이다.According to an exemplary embodiment of the present specification, B1 and B2 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic to tricyclic aliphatic hydrocarbon ring; Or a substituted or unsubstituted monocyclic to tricyclic aromatic hydrocarbon ring.

본 명세서의 일 실시상태에 따르면, B1 및 B2는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 단환의 지방족 탄화수소 고리; 또는 치환 또는 비치환된 단환의 방향족 탄화수소 고리이다.According to an exemplary embodiment of the present specification, B1 and B2 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic aliphatic hydrocarbon ring; Or a substituted or unsubstituted monocyclic aromatic hydrocarbon ring.

본 명세서의 일 실시상태에 따르면, B1 및 B2는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 벤젠고리 또는 치환 또는 비치환된 시클로헥산고리이다.According to an exemplary embodiment of the present specification, B1 and B2 are the same as or different from each other, and each independently a substituted or unsubstituted benzene ring or a substituted or unsubstituted cyclohexane ring.

본 명세서의 일 실시상태에 따르면, B1 및 B2는 서로 동일하거나 상이하고, 각각 독립적으로 벤젠고리 또는 CD3로 치환 또는 비치환된 시클로헥산고리이다.According to an exemplary embodiment of the present specification, B1 and B2 are the same as or different from each other, and each independently a benzene ring or a cyclohexane ring unsubstituted or substituted with CD 3.

본 명세서의 일 실시상태에 따르면, B1 및 B2는 벤젠고리이다.According to an exemplary embodiment of the present specification, B1 and B2 are benzene rings.

본 명세서의 일 실시상태에 따르면, B1은 벤젠고리이고, B2는 CD3로 치환 또는 비치환된 시클로헥산고리이다.According to an exemplary embodiment of the present specification, B1 is a benzene ring, and B2 is a cyclohexane ring unsubstituted or substituted with CD 3.

본 명세서의 일 실시상태에 따르면, R6 및 R7은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 30의 알킬기; 치환 또는 비치환된 탄소수 1 내지 30의 알콕시기; 치환 또는 비치환된 탄소수 1 내지 30의 알킬티옥시기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 탄소수 2 내지 30의 알케닐기; 치환 또는 비치환된 탄소수 2 내지 30의 알키닐기; 치환 또는 비치환된 아릴알킬기; 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 헤테로고리기이거나, 인접하는 기는 서로 결합하여 치환 또는 비치환된 탄소수 12 내지 30의 고리를 형성한다.According to an exemplary embodiment of the present specification, R6 and R7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C30 alkyl group; A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; A substituted or unsubstituted C 1 to C 30 alkyl thioxy group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms; A substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring having 12 to 30 carbon atoms.

본 명세서의 일 실시상태에 따르면, R6 및 R7은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 20의 알킬기; 치환 또는 비치환된 탄소수 1 내지 20의 알콕시기; 치환 또는 비치환된 탄소수 1 내지 20의 알킬티옥시기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 탄소수 2 내지 20의 알케닐기; 치환 또는 비치환된 탄소수 2 내지 20의 알키닐기; 치환 또는 비치환된 아릴알킬기; 치환 또는 비치환된 탄소수 6 내지 20의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 20의 헤테로고리기이거나, 인접하는 기는 서로 결합하여 치환 또는 비치환된 탄소수 12 내지 20의 고리를 형성한다.According to an exemplary embodiment of the present specification, R6 and R7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; A substituted or unsubstituted C 1 to C 20 alkyl thioxy group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms; A substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring having 12 to 20 carbon atoms.

본 명세서의 일 실시상태에 따르면, R6 및 R7은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 10의 알킬기; 치환 또는 비치환된 탄소수 1 내지 10의 알콕시기; 치환 또는 비치환된 탄소수 1 내지 10의 알킬티옥시기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 탄소수 2 내지 10의 알케닐기; 치환 또는 비치환된 탄소수 2 내지 10의 알키닐기; 치환 또는 비치환된 아릴알킬기; 치환 또는 비치환된 탄소수 6 내지 10의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 10의 헤테로고리기이거나, 인접하는 기는 서로 결합하여 치환 또는 비치환된 탄소수 12 내지 16의 고리를 형성한다.According to an exemplary embodiment of the present specification, R6 and R7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms; A substituted or unsubstituted C 1 to C 10 alkyl thioxy group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms; A substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted aryl group having 6 to 10 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 10 carbon atoms, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring having 12 to 16 carbon atoms.

본 명세서의 일 실시상태에 따르면, R6 및 R7은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 중수소로 치환 또는 비치환된 메틸기; 중수소로 치환 또는 비치환된 에틸기; 중수소로 치환 또는 비치환된 프로필기; 중수소로 치환 또는 비치환된 부틸기; 중수소로 치환 또는 비치환된 트리메틸실릴기; 또는 중수소 또는 CD3로 치환 또는 비치환된 페닐기이거나, R6 및 R7은 서로 결합하여 중수소, 메틸기, CD3 또는 t-부틸기로 치환 또는 비치환된 카바졸 고리; 또는 중수소, 메틸기, CD3 또는 t-부틸기로 치환 또는 비치환된 헥사하이드로카바졸 고리를 형성하거나, 인접하는 기와 서로 결합하여 중수소, 메틸기, CD3 또는 t-부틸기로 치환 또는 비치환된 시클로헥센 고리를 형성한다.According to an exemplary embodiment of the present specification, R6 and R7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium; An ethyl group unsubstituted or substituted with deuterium; A propyl group unsubstituted or substituted with deuterium; A butyl group unsubstituted or substituted with deuterium; Trimethylsilyl group unsubstituted or substituted with deuterium; Or a phenyl group unsubstituted or substituted with deuterium or CD 3 , or R6 and R7 are bonded to each other to form a carbazole ring unsubstituted or substituted with a deuterium, methyl group, CD 3 or t-butyl group; Or cyclohexene unsubstituted or substituted with deuterium, methyl group, CD 3 or t-butyl group to form a hexahydrocarbazole ring substituted or unsubstituted with a deuterium, methyl group, CD 3 or t-butyl group, or bonded to each other with adjacent groups Form a ring

본 명세서의 일 실시상태에 따르면, R6 및 R7은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 중수소로 치환 또는 비치환된 메틸기; 중수소로 치환 또는 비치환된 i-프로필기; t-부틸기; 트리메틸실릴기; 또는 페닐기이거나, R6 및 R7은 서로 결합하여 메틸기, CD3 또는 t-부틸기로 치환 또는 비치환된 카바졸 고리; 또는 메틸기, CD3 또는 t-부틸기로 치환 또는 비치환된 헥사하이드로카바졸 고리를 형성하거나, 인접하는 기와 서로 결합하여 메틸기로 치환 또는 비치환된 시클로헥센 고리를 형성한다.According to an exemplary embodiment of the present specification, R6 and R7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium; I-propyl group unsubstituted or substituted with deuterium; t-butyl group; Trimethylsilyl group; Or a phenyl group, R6 and R7 are bonded to each other to form a carbazole ring unsubstituted or substituted with a methyl group, CD 3 or t-butyl group; Or a methyl group, CD 3 or t-butyl group to form a substituted or unsubstituted hexahydrocarbazole ring, or to form a methyl group substituted or unsubstituted cyclohexene ring by bonding to each other with adjacent groups.

본 명세서의 일 실시상태에 따르면, R6 및 R7은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 중수소로 치환 또는 비치환된 메틸기; 중수소로 치환 또는 비치환된 i-프로필기; t-부틸기; 트리메틸실릴기; 또는 페닐기이거나, 인접하는 기와 서로 결합하여 하기 구조를 형성한다. 하기 구조는 중수소, 중수소로 치환 또는 비치환된 메틸기, 중수소로 치환 또는 비치환된 i-프로필기 또는 t-부틸기로 치환 또는 비치환되고,

Figure PCTKR2020012249-appb-I000043
는 화학식 1에 결합되는 위치를 의미한다.According to an exemplary embodiment of the present specification, R6 and R7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium; I-propyl group unsubstituted or substituted with deuterium; t-butyl group; Trimethylsilyl group; Or, it is a phenyl group, or combines with an adjacent group to form the following structure. The following structure is unsubstituted or substituted with deuterium, a methyl group unsubstituted or substituted with deuterium, an i-propyl group or t-butyl group substituted or unsubstituted with deuterium,
Figure PCTKR2020012249-appb-I000043
Means a position bonded to the formula (1).

Figure PCTKR2020012249-appb-I000044
Figure PCTKR2020012249-appb-I000044

본 명세서의 일 실시상태에 따르면, R6 및 R7은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 메틸기; CD3; 또는 t-부틸기이거나, R6 및 R7은 서로 결합하여 메틸기, CD3 또는 t-부틸기로 치환 또는 비치환된 카바졸 고리; 또는 메틸기, CD3 또는 t-부틸기로 치환 또는 비치환된 헥사하이드로카바졸 고리를 형성한다.According to an exemplary embodiment of the present specification, R6 and R7 are the same as or different from each other, and each independently hydrogen; Methyl group; CD 3 ; Or a t-butyl group, or R6 and R7 are bonded to each other to form a carbazole ring unsubstituted or substituted with a methyl group, CD 3 or t-butyl group; Or a methyl group, CD 3 or t-butyl group to form a substituted or unsubstituted hexahydrocarbazole ring.

본 명세서의 일 실시상태에 따르면, R6 및 R7은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 또는 t-부틸기이거나, R6 및 R7은 서로 결합하여 CD3로 치환 또는 비치환된 카바졸 고리; 또는 CD3로 치환 또는 비치환된 헥사하이드로카바졸 고리를 형성한다.According to an exemplary embodiment of the present specification, R6 and R7 are the same as or different from each other, and each independently hydrogen; Or a t-butyl group, R6 and R7 are bonded to each other to CD 3 substituted or unsubstituted carbazole ring; Or CD 3 to form a substituted or unsubstituted hexahydrocarbazole ring.

본 명세서의 일 실시상태에 따르면, Y가 상기 화학식 2로 표시되는 경우, X1, X2 및 R1 내지 R7 중 적어도 하나는 중수소로 치환된 탄소수 1 내지 3의 알킬기이다.According to an exemplary embodiment of the present specification, when Y is represented by Formula 2, at least one of X1, X2 and R1 to R7 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium.

본 명세서의 일 실시상태에 따르면, Y가 상기 화학식 2로 표시되는 경우, R1 내지 R7 중 적어도 하나는 중수소로 치환된 탄소수 1 내지 3의 알킬기이다.According to an exemplary embodiment of the present specification, when Y is represented by Formula 2, at least one of R1 to R7 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium.

본 명세서의 일 실시상태에 따르면, X1, X2 및 R1 내지 R7 중 적어도 2개는 중수소로 치환된 탄소수 1 내지 3의 알킬기이다.According to an exemplary embodiment of the present specification, at least two of X1, X2, and R1 to R7 are an alkyl group having 1 to 3 carbon atoms substituted with deuterium.

본 명세서의 일 실시상태에 따르면, X1, X2 및 R1 내지 R7 중 적어도 3개는 중수소로 치환된 탄소수 1 내지 3의 알킬기이다.According to an exemplary embodiment of the present specification, at least three of X1, X2, and R1 to R7 are an alkyl group having 1 to 3 carbon atoms substituted with deuterium.

본 명세서의 일 실시상태에 따르면, X1, X2 및 R1 내지 R7 중 적어도 하나는 중수소로 치환된 메틸기; 중수소로 치환된 에틸기; 또는 중수소로 치환된 프로필기 중 선택된다.According to an exemplary embodiment of the present specification, at least one of X1, X2, and R1 to R7 is a methyl group substituted with deuterium; An ethyl group substituted with deuterium; Or it is selected from a propyl group substituted with deuterium.

본 명세서의 일 실시상태에 따르면, X1, X2 및 R1 내지 R7 중 적어도 하나는 중수소로 치환된 메틸기; 중수소로 치환된 에틸기; 또는 중수소로 치환된 i-프로필기 중 선택된다.According to an exemplary embodiment of the present specification, at least one of X1, X2, and R1 to R7 is a methyl group substituted with deuterium; An ethyl group substituted with deuterium; Or it is selected from i-propyl group substituted with deuterium.

본 명세서의 일 실시상태에 따르면, X1, X2 및 R1 내지 R7 중 적어도 2개는 중수소로 치환된 메틸기; 중수소로 치환된 에틸기; 또는 중수소로 치환된 i-프로필기 중 선택된다.According to an exemplary embodiment of the present specification, at least two of X1, X2, and R1 to R7 are methyl groups substituted with deuterium; An ethyl group substituted with deuterium; Or it is selected from i-propyl group substituted with deuterium.

본 명세서의 일 실시상태에 따르면, X1, X2 및 R1 내지 R7 중 적어도 3개는 중수소로 치환된 메틸기; 중수소로 치환된 에틸기; 또는 중수소로 치환된 i-프로필기 중 선택된다.According to an exemplary embodiment of the present specification, at least three of X1, X2, and R1 to R7 are methyl groups substituted with deuterium; An ethyl group substituted with deuterium; Or it is selected from i-propyl group substituted with deuterium.

본 명세서의 일 실시상태에 따르면, 상기 R1 내지 R7 중 적어도 2개는 중수소로 치환된 탄소수 1 내지 3의 알킬기이다.According to an exemplary embodiment of the present specification, at least two of R1 to R7 are an alkyl group having 1 to 3 carbon atoms substituted with deuterium.

본 명세서의 일 실시상태에 따르면, 상기 R1 내지 R7 중 적어도 3개는 중수소로 치환된 탄소수 1 내지 3의 알킬기이다.According to an exemplary embodiment of the present specification, at least three of R1 to R7 are an alkyl group having 1 to 3 carbon atoms substituted with deuterium.

본 명세서의 일 실시상태에 따르면, R1 내지 R7 중 적어도 하나는 -CD3; -C2D5; CH2CD3; CD(CD3)2 또는 CH(CD3)2 중 선택된다.According to an exemplary embodiment of the present specification, at least one of R1 to R7 is -CD 3 ; -C 2 D 5 ; CH 2 CD 3 ; It is selected from CD(CD 3 ) 2 or CH(CD 3 ) 2 .

본 명세서의 일 실시상태에 따르면, R1 내지 R7 중 적어도 2개는 -CD3; -C2D5; CH2CD3; CD(CD3)2 또는 CH(CD3)2 중 선택된다.According to an exemplary embodiment of the present specification, at least two of R1 to R7 are -CD 3 ; -C 2 D 5 ; CH 2 CD 3 ; It is selected from CD(CD 3 ) 2 or CH(CD 3 ) 2 .

본 명세서의 일 실시상태에 따르면, R1 내지 R7 중 적어도 3개는 -CD3; -C2D5; CH2CD3; CD(CD3)2 또는 CH(CD3)2 중 선택된다.According to an exemplary embodiment of the present specification, at least three of R1 to R7 are -CD 3 ; -C 2 D 5 ; CH 2 CD 3 ; It is selected from CD(CD 3 ) 2 or CH(CD 3 ) 2 .

본 명세서의 일 실시상태에 따르면, R1 내지 R7 중 적어도 하나는 CD3이다.According to an exemplary embodiment of the present specification, at least one of R1 to R7 is CD 3 .

본 명세서의 일 실시상태에 따르면, R1 내지 R7 중 적어도 2개는 CD3이다.According to an exemplary embodiment of the present specification, at least two of R1 to R7 are CD 3 .

본 명세서의 일 실시상태에 따르면, R1 내지 R7 중 적어도 3개는 CD3이다.According to an exemplary embodiment of the present specification, at least three of R1 to R7 are CD 3 .

본 명세서의 일 실시상태에 따르면, r1 및 r2는 서로 동일하거나 상이하고, 각각 독립적으로 1 내지 3의 정수이다.According to an exemplary embodiment of the present specification, r1 and r2 are the same as or different from each other, and are each independently an integer of 1 to 3.

본 명세서의 일 실시상태에 따르면, r1 및 r2는 서로 동일하거나 상이하고, 각각 독립적으로 1 또는 2이다.According to an exemplary embodiment of the present specification, r1 and r2 are the same as or different from each other, and are each independently 1 or 2.

본 명세서의 일 실시상태에 따르면, r3 및 r5 내지 r7는 서로 동일하거나 상이하고, 각각 독립적으로 1 내지 11의 정수이다.According to an exemplary embodiment of the present specification, r3 and r5 to r7 are the same as or different from each other, and are each independently an integer of 1 to 11.

본 명세서의 일 실시상태에 따르면, r3 및 r5 내지 r7는 서로 동일하거나 상이하고, 각각 독립적으로 1 내지 9의 정수이다.According to an exemplary embodiment of the present specification, r3 and r5 to r7 are the same as or different from each other, and are each independently an integer of 1 to 9.

본 명세서의 일 실시상태에 따르면, r3 및 r5 내지 r7는 서로 동일하거나 상이하고, 각각 독립적으로 1 내지 5의 정수이다.According to an exemplary embodiment of the present specification, r3 and r5 to r7 are the same as or different from each other, and are each independently an integer of 1 to 5.

본 명세서의 일 실시상태에 따르면, r3 및 r5 내지 r7는 서로 동일하거나 상이하고, 각각 독립적으로 1 내지 3의 정수이다.According to an exemplary embodiment of the present specification, r3 and r5 to r7 are the same as or different from each other, and are each independently an integer of 1 to 3.

본 명세서의 일 실시상태에 따르면, r4는 1 또는 2의 정수이다.According to an exemplary embodiment of the present specification, r4 is an integer of 1 or 2.

본 명세서의 일 실시상태에 따르면, r4는 1이다.According to an exemplary embodiment of the present specification, r4 is 1.

본 명세서의 일 실시상태에 따르면, r4는 2이다.According to an exemplary embodiment of the present specification, r4 is 2.

본 명세서의 일 실시상태에 따르면, n은 1 또는 2의 정수이다.According to an exemplary embodiment of the present specification, n is an integer of 1 or 2.

본 명세서의 일 실시상태에 따르면, n은 1이다.According to an exemplary embodiment of the present specification, n is 1.

본 명세서의 일 실시상태에 따르면, n은 2이다.According to an exemplary embodiment of the present specification, n is 2.

본 명세서의 일 실시상태에 따르면, r4+n는 2 또는 3의 정수이다.According to an exemplary embodiment of the present specification, r4+n is an integer of 2 or 3.

본 명세서의 일 실시상태에 따르면, r1 내지 r7 및 n이 각각 2 이상인 경우, 각각의 괄호 안의 치환기는 서로 동일하거나 상이하다.According to an exemplary embodiment of the present specification, when r1 to r7 and n are each 2 or more, the substituents in each parenthesis are the same as or different from each other.

본 명세서의 일 실시상태에 따르면, 상기 화학식 2(

Figure PCTKR2020012249-appb-I000045
)는 하기 화학식 201 내지 203 중 어느 하나로 표시된다.According to an exemplary embodiment of the present specification, Formula 2 (
Figure PCTKR2020012249-appb-I000045
) Is represented by any one of the following Chemical Formulas 201 to 203.

[화학식 201]　　　　　　　　[화학식 202]　　　　　　[화학식 203][Chemical Formula 201]　　　　　　　　[Chemical Formula 202]　　　　　　[Chemical Formula 203]

Figure PCTKR2020012249-appb-I000046
Figure PCTKR2020012249-appb-I000046

상기 화학식 201 내지 203에 있어서,In Formulas 201 to 203,

G6 및 G7은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 알키닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 아릴알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성하고,G6 and G7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkyl thioxy group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combined with an adjacent group to form a substituted or unsubstituted ring,

G16 및 G17은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 또는 치환 또는 비치환된 알킬기이고,G16 and G17 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group,

g6 및 g7는 각각 1 내지 5의 정수이고, g6' 및 g7'은 1 내지 4의 정수이고, g7''은 1 내지 8의 정수이고,g6 and g7 are each an integer of 1 to 5, g6' and g7' are an integer of 1 to 4, and g7'' is an integer of 1 to 8,

g6, g7, g6', g7' 및 g7''이 각각 2 이상인 경우, 2 이상의 G6 및 G7은 각각 서로 동일하거나 상이하고,When g6, g7, g6', g7' and g7'' are each 2 or more, 2 or more G6 and G7 are each the same as or different from each other,

Figure PCTKR2020012249-appb-I000047
는 화학식 1에 결합되는 위치를 의미한다.
Figure PCTKR2020012249-appb-I000047
Means a position bonded to the formula (1).

본 명세서의 일 실시상태에 따르면, G6 및 G7의 정의는 전술한 R6 및 R7의 정의와 같다.According to an exemplary embodiment of the present specification, the definitions of G6 and G7 are the same as those of R6 and R7 described above.

본 명세서의 일 실시상태에 따르면, G16 및 G17은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 또는 치환 또는 비치환된 탄소수 1 내지 20의 알킬기이다.According to an exemplary embodiment of the present specification, G16 and G17 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted C 1 to C 20 alkyl group.

본 명세서의 일 실시상태에 따르면, G16 및 G17은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 또는 치환 또는 비치환된 탄소수 1 내지 10의 알킬기이다.According to an exemplary embodiment of the present specification, G16 and G17 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted C 1 to C 10 alkyl group.

본 명세서의 일 실시상태에 따르면, G16 및 G17은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 또는 중수소로 치환 또는 비치환된 알킬기이다.According to an exemplary embodiment of the present specification, G16 and G17 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or an alkyl group unsubstituted or substituted with deuterium.

본 명세서의 일 실시상태에 따르면, G16 및 G17은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 또는 중수소로 치환 또는 비치환된 메틸기이다.According to an exemplary embodiment of the present specification, G16 and G17 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a methyl group unsubstituted or substituted with deuterium.

본 명세서의 일 실시상태에 따르면, G16 및 G17은 메틸기 또는 CD3이다.According to an exemplary embodiment of the present specification, G16 and G17 are methyl groups or CD 3 .

본 명세서의 일 실시상태에 따르면, 상기 화학식 2는 하기 구조식 중 어느 하나로 표시된다.According to an exemplary embodiment of the present specification, Chemical Formula 2 is represented by any one of the following structural formulas.

Figure PCTKR2020012249-appb-I000048
Figure PCTKR2020012249-appb-I000048

상기 구조식에서

Figure PCTKR2020012249-appb-I000049
는 결합위치를 의미한다.In the above structural formula
Figure PCTKR2020012249-appb-I000049
Means the bonding position.

본 명세서의 일 실시상태에 따르면, 상기 g6, g7, g6', g7' 및 g7''은 각각 1 내지 4의 정수이다.According to an exemplary embodiment of the present specification, g6, g7, g6', g7', and g7'' are integers of 1 to 4, respectively.

본 명세서의 일 실시상태에 따르면, 상기 g6, g7, g6', g7' 및 g7''은 각각 1 내지 3의 정수이다.According to the exemplary embodiment of the present specification, g6, g7, g6', g7', and g7'' are integers of 1 to 3, respectively.

본 명세서의 일 실시상태에 따르면, 상기 g6, g7, g6', g7' 및 g7''은 각각 1 또는 2이다.According to an exemplary embodiment of the present specification, g6, g7, g6', g7', and g7'' are 1 or 2, respectively.

본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 1-1 또는 1-2로 표시된다.According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by the following Chemical Formula 1-1 or 1-2.

[화학식 1-1][Formula 1-1]

Figure PCTKR2020012249-appb-I000050
Figure PCTKR2020012249-appb-I000050

[화학식 1-2][Formula 1-2]

Figure PCTKR2020012249-appb-I000051
Figure PCTKR2020012249-appb-I000051

상기 화학식 1-1 및 1-2에 있어서, In Formulas 1-1 and 1-2,

R1 내지 R7, A1, A2, B1, B2, X1, X2 및 r1 내지 r7의 정의는 상기 화학식 1에서의 정의와 같고,The definitions of R1 to R7, A1, A2, B1, B2, X1, X2 and r1 to r7 are the same as those in Formula 1,

Z는 중수소로 치환된 탄소수 1 내지 3의 알킬기이고,Z is an alkyl group having 1 to 3 carbon atoms substituted with deuterium,

m은 1 또는 2의 정수이고, m이 2인 경우, Z는 서로 동일하거나 상이하고,m is an integer of 1 or 2, and when m is 2, Z is the same as or different from each other,

r4+m은 2 또는 3의 정수이다.r4+m is an integer of 2 or 3.

본 명세서의 일 실시상태에 따르면, Z는 중수소로 치환된 메틸기; 중수소로 치환된 에틸기; 또는 중수소로 치환된 프로필기이다.According to an exemplary embodiment of the present specification, Z is a methyl group substituted with deuterium; An ethyl group substituted with deuterium; Or it is a propyl group substituted with deuterium.

본 명세서의 일 실시상태에 따르면, Z는 중수소로 치환된 메틸기; 중수소로 치환된 에틸기; 또는 중수소로 치환된 i-프로필기이다.According to an exemplary embodiment of the present specification, Z is a methyl group substituted with deuterium; An ethyl group substituted with deuterium; Or an i-propyl group substituted with deuterium.

본 명세서의 일 실시상태에 따르면, Z는 중수소로 치환된 메틸기이다.According to an exemplary embodiment of the present specification, Z is a methyl group substituted with deuterium.

본 명세서의 일 실시상태에 따르면, Z는 CDH2; CD2H 또는 CD3이다.According to an exemplary embodiment of the present specification, Z is CDH 2 ; It is either CD 2 H or CD 3.

본 명세서의 일 실시상태에 따르면, Z는 CD3이다.According to an exemplary embodiment of the present specification, Z is CD 3 .

본 명세서의 일 실시상태에 따르면, m은 1 또는 2의 정수이다.According to an exemplary embodiment of the present specification, m is an integer of 1 or 2.

본 명세서의 일 실시상태에 따르면, m은 1 이다.According to an exemplary embodiment of the present specification, m is 1.

본 명세서의 일 실시상태에 따르면, m은 2 이다.According to an exemplary embodiment of the present specification, m is 2.

본 명세서의 일 실시상태에 따르면, 상기 화학식 1-1에서 X1, X2 및 R1 내지 R5 중 적어도 하나는 중수소로 치환된 탄소수 1 내지 3의 알킬기이다.According to an exemplary embodiment of the present specification, in Formula 1-1, at least one of X1, X2, and R1 to R5 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium.

본 명세서의 일 실시상태에 따르면, 상기 화학식 1-1에서 R1 내지 R5 중 적어도 하나는 중수소로 치환된 탄소수 1 내지 3의 알킬기이다.According to an exemplary embodiment of the present specification, at least one of R1 to R5 in Formula 1-1 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium.

본 명세서의 일 실시상태에 따르면, 상기 화학식 1-2에서 X1, X2 및 R1 내지 R7 중 적어도 하나는 중수소로 치환된 탄소수 1 내지 3의 알킬기이다.According to an exemplary embodiment of the present specification, at least one of X1, X2, and R1 to R7 in Formula 1-2 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium.

본 명세서의 일 실시상태에 따르면, 상기 화학식 1-2에서 R1 내지 R7 중 적어도 하나는 중수소로 치환된 탄소수 1 내지 3의 알킬기이다.According to an exemplary embodiment of the present specification, at least one of R1 to R7 in Formula 1-2 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium.

본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 1-3 내지 1-7 중 어느 하나로 표시된다.According to an exemplary embodiment of the present specification, Formula 1 is represented by any one of the following Formulas 1-3 to 1-7.

[화학식 1-3][Formula 1-3]

Figure PCTKR2020012249-appb-I000052
Figure PCTKR2020012249-appb-I000052

[화학식 1-4][Formula 1-4]

Figure PCTKR2020012249-appb-I000053
Figure PCTKR2020012249-appb-I000053

[화학식 1-5][Formula 1-5]

Figure PCTKR2020012249-appb-I000054
Figure PCTKR2020012249-appb-I000054

[화학식 1-6][Formula 1-6]

Figure PCTKR2020012249-appb-I000055
Figure PCTKR2020012249-appb-I000055

[화학식 1-7][Formula 1-7]

Figure PCTKR2020012249-appb-I000056
Figure PCTKR2020012249-appb-I000056

상기 화학식 1-3 내지 1-7에 있어서,In Formulas 1-3 to 1-7,

R1 내지 R7, X1, X2 및 r1 내지 r7의 정의는 상기 화학식 1에서의 정의와 같고,The definitions of R1 to R7, X1, X2 and r1 to r7 are the same as those in Formula 1,

Z는 중수소로 치환된 탄소수 1 내지 3의 알킬기이고,Z is an alkyl group having 1 to 3 carbon atoms substituted with deuterium,

m은 1 또는 2의 정수이고, m이 2인 경우, Z는 서로 동일하거나 상이하다.m is an integer of 1 or 2, and when m is 2, Z is the same as or different from each other.

본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 1-8로 표시된다.According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by the following Chemical Formula 1-8.

[화학식 1-8][Formula 1-8]

Figure PCTKR2020012249-appb-I000057
Figure PCTKR2020012249-appb-I000057

상기 화학식 1-8에 있어서,In Formula 1-8,

A1, A2, R1 내지 R5, r1 내지 r5, Y 및 n의 정의는 화학식 1에서의 정의와 같고,The definitions of A1, A2, R1 to R5, r1 to r5, Y and n are the same as those in Formula 1,

X3은 CRaRb, NRc, O, PRd, S, PORe, SO2, SiRfRg 또는 BRh이고,X3 is CRaRb, NRc, O, PRd, S, PORe, SO 2 , SiRfRg or BRh,

Ra 내지 Rh는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 알키닐기; 치환 또는 비치환된 아릴알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 인접하는 기는 서로 결합하여 치환 또는 비치환된 고리를 형성한다.Ra To Rh are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring.

본 명세서의 일실시상태에 따르면, 상기 화학식 1-8에서의 Ra 내지 Rh의 정의는 화학식 1에서의 Ra 내지 Rh의 정의와 같다.According to an exemplary embodiment of the present specification, the definition of Ra to Rh in Formula 1-8 is the same as the definition of Ra to Rh in Formula 1.

본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 1-9 또는 1-10으로 표시된다.According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by the following Chemical Formula 1-9 or 1-10.

[화학식 1-9][Formula 1-9]

Figure PCTKR2020012249-appb-I000058
Figure PCTKR2020012249-appb-I000058

[화학식 1-10][Formula 1-10]

Figure PCTKR2020012249-appb-I000059
Figure PCTKR2020012249-appb-I000059

상기 화학식 1-9 및 1-10 에 있어서,In Formulas 1-9 and 1-10,

X1, X2, A1, A2, R1, R3 내지 R5, r1, r3 내지 r5, Y 및 n의 정의는 화학식 1에서의 정의와 같고,The definitions of X1, X2, A1, A2, R1, R3 to R5, r1, r3 to r5, Y and n are the same as those in Formula 1,

A3 및 A4는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 지방족 탄화수소 고리; 치환 또는 비치환된 방향족 탄화수소 고리; 치환 또는 비치환된 방향족 헤테로고리; 또는 치환 또는 비치환된 지방족 탄화수소고리 및 방향족 탄화수소고리의 축합고리이고,A3 and A4 are the same as or different from each other, and each independently a substituted or unsubstituted aliphatic hydrocarbon ring; A substituted or unsubstituted aromatic hydrocarbon ring; Substituted or unsubstituted aromatic heterocycle; Or a condensed ring of a substituted or unsubstituted aliphatic hydrocarbon ring and an aromatic hydrocarbon ring,

R21 및 R22는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성하고,R21 and R22 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combined with an adjacent group to form a substituted or unsubstituted ring,

r21 및 r22는 각각 1 내지 9의 정수이고,r21 and r22 are each an integer of 1 to 9,

r21 및 r22가 각각 2 이상인 경우, 2 이상의 R21 및 R22는 각각 서로 같거나 상이하다.When r21 and r22 are each 2 or more, two or more R21 and R22 are each the same as or different from each other.

본 명세서의 일 실시상태에 따르면, A3은 하기 구조식 중 어느 하나로 표시된다.According to an exemplary embodiment of the present specification, A3 is represented by any one of the following structural formulas.

본 명세서의 일 실시상태에 따르면, 상기 A3 및 A4에는 전술한 R1 또는 R2가 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성하는 경우에 대한 정의가 적용된다.According to an exemplary embodiment of the present specification, the definition of a case where R1 or R2 is bonded to each other to form a substituted or unsubstituted ring is applied to A3 and A4.

본 명세서의 일 실시상태에 따르면, 상기 A3 및 A4는 서로 동일하거나 상이하고, 각각 독립적으로 하기 구조들 중 어느 하나로 표시된다.According to an exemplary embodiment of the present specification, A3 and A4 are the same as or different from each other, and are each independently represented by any one of the following structures.

Figure PCTKR2020012249-appb-I000060
Figure PCTKR2020012249-appb-I000060

상기 구조들에 있어서, *는 형성된 고리가 축합되는 위치를 의미하고, 상기 구조들은 중수소; 또는 중수소로 치환 또는 비치환된 알킬기로 치환 또는 비치환된다.In the above structures, * means a position at which the formed ring is condensed, and the structures include deuterium; Or it is unsubstituted or substituted with a deuterium-substituted or unsubstituted alkyl group.

본 명세서의 일 실시상태에 따르면, 상기 R21 및 R22에는 전술한 P1의 정의가 적용된다.According to an exemplary embodiment of the present specification, the above-described definition of P1 is applied to R21 and R22.

본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 1-11 또는 1-12로 표시된다.According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by the following Chemical Formulas 1-11 or 1-12.

[화학식 1-11][Formula 1-11]

Figure PCTKR2020012249-appb-I000061
Figure PCTKR2020012249-appb-I000061

[화학식 1-12][Formula 1-12]

Figure PCTKR2020012249-appb-I000062
Figure PCTKR2020012249-appb-I000062

상기 화학식 1-11 및 1-12에 있어서,In Formulas 1-11 and 1-12,

X1, X2, R1 내지 R5, r1, r3, r4, A1, Y 및 n의 정의는 상기 화학식 1에서의 정의와 같고,The definitions of X1, X2, R1 to R5, r1, r3, r4, A1, Y and n are the same as those in Formula 1,

X101은 직접결합; 또는 -BR103-이고,X101 is a direct bond; Or -BR103-,

R103, G101 및 G102은 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기이고,R103, G101 and G102 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,

r2' 는 1 또는 2이고,r2' is 1 or 2,

r5'는 1 내지 4의 정수이고,r5' is an integer from 1 to 4,

r5''는 1 내지 8의 정수이고,r5'' is an integer from 1 to 8,

r2', r5' 및 r5''가 각각 2 이상인 경우, 2 이상의 R2 및 R5는 각각 서로 동일하거나 상이하다.When r2', r5' and r5'' are each 2 or more, two or more R2 and R5 are each the same as or different from each other.

본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화합물 중 어느 하나로 표시된다.According to an exemplary embodiment of the present specification, Formula 1 is represented by any one of the following compounds.

Figure PCTKR2020012249-appb-I000063
Figure PCTKR2020012249-appb-I000063

Figure PCTKR2020012249-appb-I000064
Figure PCTKR2020012249-appb-I000064

Figure PCTKR2020012249-appb-I000065
Figure PCTKR2020012249-appb-I000065

Figure PCTKR2020012249-appb-I000066
Figure PCTKR2020012249-appb-I000066

Figure PCTKR2020012249-appb-I000067
Figure PCTKR2020012249-appb-I000067

Figure PCTKR2020012249-appb-I000068
Figure PCTKR2020012249-appb-I000068

Figure PCTKR2020012249-appb-I000069
Figure PCTKR2020012249-appb-I000069

Figure PCTKR2020012249-appb-I000070
Figure PCTKR2020012249-appb-I000070

Figure PCTKR2020012249-appb-I000071
Figure PCTKR2020012249-appb-I000071

Figure PCTKR2020012249-appb-I000072
Figure PCTKR2020012249-appb-I000072

Figure PCTKR2020012249-appb-I000073
Figure PCTKR2020012249-appb-I000073

Figure PCTKR2020012249-appb-I000074
Figure PCTKR2020012249-appb-I000074

Figure PCTKR2020012249-appb-I000075
Figure PCTKR2020012249-appb-I000075

Figure PCTKR2020012249-appb-I000076
Figure PCTKR2020012249-appb-I000076

Figure PCTKR2020012249-appb-I000077
Figure PCTKR2020012249-appb-I000077

Figure PCTKR2020012249-appb-I000078
Figure PCTKR2020012249-appb-I000078

Figure PCTKR2020012249-appb-I000079
Figure PCTKR2020012249-appb-I000079

Figure PCTKR2020012249-appb-I000080
Figure PCTKR2020012249-appb-I000080

Figure PCTKR2020012249-appb-I000081
Figure PCTKR2020012249-appb-I000081

Figure PCTKR2020012249-appb-I000082
Figure PCTKR2020012249-appb-I000082

Figure PCTKR2020012249-appb-I000083
Figure PCTKR2020012249-appb-I000083

Figure PCTKR2020012249-appb-I000084
Figure PCTKR2020012249-appb-I000084

Figure PCTKR2020012249-appb-I000085
Figure PCTKR2020012249-appb-I000085

Figure PCTKR2020012249-appb-I000086
Figure PCTKR2020012249-appb-I000086

Figure PCTKR2020012249-appb-I000087
Figure PCTKR2020012249-appb-I000087

Figure PCTKR2020012249-appb-I000088
Figure PCTKR2020012249-appb-I000088

Figure PCTKR2020012249-appb-I000089
Figure PCTKR2020012249-appb-I000089

Figure PCTKR2020012249-appb-I000090
Figure PCTKR2020012249-appb-I000090

Figure PCTKR2020012249-appb-I000091
Figure PCTKR2020012249-appb-I000091

Figure PCTKR2020012249-appb-I000092
Figure PCTKR2020012249-appb-I000092

Figure PCTKR2020012249-appb-I000093
Figure PCTKR2020012249-appb-I000093

본 발명에서는 상기와 같이 코어 구조에 다양한 치환기를 도입함으로써 다양한 에너지 밴드갭을 갖는 화합물을 합성할 수 있다. 또한, 본 발명에서는 상기와 같은 구조의 코어 구조에 다양한 치환기를 도입함으로써 화합물의 HOMO 및 LUMO 에너지 준위도 조절할 수 있다.In the present invention, compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure as described above. In addition, in the present invention, the HOMO and LUMO energy levels of the compound can be adjusted by introducing various substituents to the core structure of the above structure.

본 발명의 화학식 1의 화합물은 하기 반응식과 같이 코어구조가 제조될 수 있다. 치환기는 당 기술분야에 알려져 있는 방법에 의하여 결합될 수 있으며, 치환기의 종류, 위치 및 개수는 당 기술분야에 알려져 있는 기술에 따라 변경될 수 있다.The compound of Formula 1 of the present invention may have a core structure as shown in the following scheme. Substituents may be bonded by methods known in the art, and the type, position, and number of substituents may be changed according to techniques known in the art.

<반응식><Reaction Scheme>

[일반식 1][General Formula 1]

Figure PCTKR2020012249-appb-I000094
Figure PCTKR2020012249-appb-I000094

　　　　　　　　　　　　　[중간체 1]　　　　　　　[최종생성물 1][Intermediate 1]　　　　　　　[Final Product 1]

상기 일반식 1에서, Y는 중수소로 치환된 탄소수 1 내지 3의 알킬기; 또는 치환 또는 비치환된 아민기이고, n은 1 내지 3이다.In General Formula 1, Y is an alkyl group having 1 to 3 carbon atoms substituted with deuterium; Or a substituted or unsubstituted amine group, and n is 1 to 3.

상기 일반식 1에서, 중수소 치환 알킬기 또는 아민기를 포함한 다이브로모벤젠 화합물과, 중수소 치환 알킬기를 포함하거나 포함하지 않은 다이아릴아민 화합물로부터 Buckwald-Hartwig amination 반응을 이용하여 동일한 아민기를 갖는 [중간체 1]를 얻는다. 이어서 보론트리아이오다이드를 이용해 보론을 도입하여 상기 [최종 생성물 1]을 합성할 수 있다.In General Formula 1, [Intermediate 1] having the same amine group using a Buckwald-Hartwig amination reaction from a dibromobenzene compound containing a deuterium substituted alkyl group or an amine group and a diarylamine compound containing or not containing a deuterium substituted alkyl group Get Subsequently, boron can be introduced using boron triiodide to synthesize the [final product 1].

[일반식 2][General Formula 2]

Figure PCTKR2020012249-appb-I000095
　　　　　　　　　　　[중간체 2-a]　　　　[중간체 2-b]　　　　[최종 생성물 2]
Figure PCTKR2020012249-appb-I000095
[Intermediate 2-a] [Intermediate 2-b] [Final Product 2]

상기 일반식 2에서, Y는 중수소로 치환된 탄소수 1 내지 3의 알킬기; 또는 치환 또는 비치환된 아민기이고, n은 1 내지 3이다.In the general formula 2, Y is an alkyl group having 1 to 3 carbon atoms substituted with deuterium; Or a substituted or unsubstituted amine group, and n is 1 to 3.

상기 일반식 2에서, 중수소 치환 알킬기 또는 아민기를 포함한 브로모클로로벤젠 화합물과, 중수소 치환 알킬기를 포함하거나 포함하지 않은 다이아릴아민 화합물로부터 두 번의 Buckwald-Hartwig amination 반응을 이용하여 각각 다른 아민기를 포함하는 [중간체2-b]를 얻는다. 이어서 보론트리아이오다이드를 이용해 보론을 도입하여 상기 [최종 생성물 2]를 합성할 수 있다.In General Formula 2, each containing a different amine group using two Buckwald-Hartwig amination reactions from a bromochlorobenzene compound containing a deuterium substituted alkyl group or an amine group, and a diarylamine compound containing or not containing a deuterium substituted alkyl group. [Intermediate 2-b] is obtained. Subsequently, boron can be introduced using boron triiodide to synthesize the [final product 2].

[일반식 3][General Formula 3]

Figure PCTKR2020012249-appb-I000096
Figure PCTKR2020012249-appb-I000096

　　　[중간체 3]　　　　　　　　　　　　　　[최종생성물 3][Intermediate 3]　　　　　　　　　　　　　　[Final Product 3]

메틸기가 포함된 보론화합물인 [중간체 3]으로부터 전이금속 촉매를 이용한 중수소 치환 반응을 이용하여 중수소 치환 메틸기를 도입할 수 있다. 상기 반응식 3에서는 특정 위치에 메틸기가 존재하는 화학물을 예시하였으나, 메틸기 외에도 보론 화합물의 다양한 위치에 존재하는 알킬기들의 C-H 결합을 15% 이상의 치환율로 C-D 결합으로 바꾸어 중수소 치환 알킬기를 도입할 수 있다.A deuterium substituted methyl group may be introduced from [Intermediate 3], which is a boron compound containing a methyl group, using a deuterium substitution reaction using a transition metal catalyst. In Reaction Scheme 3, a chemical substance having a methyl group at a specific position is illustrated, but a deuterium substituted alkyl group may be introduced by replacing the C-H bond of the alkyl groups present at various positions of the boron compound in addition to the methyl group to a C-D bond with a substitution rate of 15% or more.

전술한 화학물의 컨쥬게이션 길이와 에너지 밴드갭은 밀접한 관계가 있다. 구체적으로, 화학물의 컨쥬게이션 길이가 길수록 에너지 밴드갭이 작아진다.The conjugation length and energy band gap of the aforementioned chemicals are closely related. Specifically, the longer the conjugation length of the chemical, the smaller the energy band gap.

본 발명에서는 상기와 같이 코어 구조에 다양한 치환기를 도입함으로써 다양한 에너지 밴드갭을 갖는 화합물을 합성할 수 있다. 또한, 본 발명에서는 상기와 같은 구조의 코어 구조에 다양한 치환기를 도입함으로써 화합물의 HOMO 및 LUMO 에너지 준위를 조절하고, 이렇게 도입된 치환기 중 메틸기의 C-H 결합을 더 단단한 C-D 결합으로 바꾸어줌으로써 광학 특성과 수명 특성이 함께 개선된 화합물을 합성할 수 있다.In the present invention, compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure as described above. In addition, in the present invention, by introducing various substituents to the core structure of the above structure, the HOMO and LUMO energy levels of the compound are adjusted, and the CH bond of the methyl group among the introduced substituents is changed to a harder CD bond, thereby optical properties and lifetime. Compounds with improved properties can be synthesized.

또한, 본 명세서는 상기 전술한 화합물을 포함하는 유기 발광 소자를 제공한다.In addition, the present specification provides an organic light-emitting device including the above-described compound.

본 명세서의 일 실시상태에 있어서, 제1 전극; 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 상기 화합물을 포함하는 것인 유기 발광 소자를 제공한다. In an exemplary embodiment of the present specification, the first electrode; A second electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound.

본 명세서에서 어떤 부재가 다른 부재 "상에" 위치하고 있다고 할 때, 이는 어떤 부재가 다른 부재에 접해 있는 경우뿐 아니라 두 부재 사이에 또 다른 부재가 존재하는 경우도 포함한다.In this specification, when a member is positioned "on" another member, this includes not only the case where the member is in contact with the other member, but also the case where another member exists between the two members.

본 명세서에서 어떤 부분이 어떤 구성요소를 "포함" 한다고 할 때, 이는 특별히 반대되는 기재가 없는 한 다른 구성요소를 제외하는 것이 아니라 다른 구성 요소를 더 포함할 수 있는 것을 의미한다. In the present specification, when a part "includes" a certain component, it means that other components may be further included rather than excluding other components unless specifically stated to the contrary.

본 명세서의 유기 발광 소자의 유기물층은 단층 구조로 이루어질 수도 있으나, 2층 이상의 유기물층이 적층된 다층 구조로 이루어질 수 있다. 예컨대, 본 명세서의 유기 발광 소자의 대표적인 예로서, 유기 발광 소자는 유기물층으로서 정공 주입층, 정공 수송층, 발광층, 전자 수송층, 전자 주입층, 전자 차단층, 정공 차단층 등을 포함하는 구조를 가질 수 있다. 그러나 유기 발광 소자의 구조는 이에 한정되지 않고 더 적은 수의 유기물층을 포함할 수 있다.The organic material layer of the organic light emitting device of the present specification may have a single-layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, as a representative example of the organic light emitting device of the present specification, the organic light emitting device may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, etc. as an organic material layer. have. However, the structure of the organic light emitting device is not limited thereto, and may include a smaller number of organic material layers.

본 명세서의 일 실시상태에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화학식 1로 표시되는 화합물을 포함한다. In the exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes the compound represented by Formula 1 above.

본 명세서의 일 실시상태에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화학식 1로 표시되는 화합물을 발광층의 도펀트로서 포함한다.In the exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes the compound represented by Formula 1 as a dopant of the emission layer.

본 명세서의 일 실시상태에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화학식 1로 표시되는 화합물을 발광층의 청색 형광 도펀트로서 포함한다.In the exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes the compound represented by Formula 1 as a blue fluorescent dopant of the emission layer.

본 명세서의 일 실시상태에 있어서, 상기 유기물층은 정공 주입층 또는 정공 수송층을 포함하고, 상기 정공 주입층 또는 정공 수송층은 상기 화학식 1로 표시되는 화합물을 포함한다. In the exemplary embodiment of the present specification, the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the compound represented by Formula 1 above.

본 명세서의 일 실시상태에 있어서, 상기 유기물층은 전자 주입층, 전자 수송층 또는 전자 주입 및 수송을 동시에 하는 층을 포함하고, 상기 전자 주입층, 전자 수송층 또는 전자 주입 및 수송을 동시에 하는 층은 상기 화학식 1로 표시되는 화합물을 포함한다. In the exemplary embodiment of the present specification, the organic material layer includes an electron injection layer, an electron transport layer, or a layer that simultaneously injects and transports electrons, and the electron injection layer, the electron transport layer, or a layer that simultaneously injects and transports electrons is the formula Including the compound represented by 1.

본 명세서의 일 실시상태에 있어서, 상기 유기물층은 전자 차단층을 포함하고, 상기 전자 차단층은 상기 화학식 1로 표시되는 화합물을 포함한다. In the exemplary embodiment of the present specification, the organic material layer includes an electron blocking layer, and the electron blocking layer includes the compound represented by Formula 1 above.

본 명세서의 일 실시상태에 있어서, 상기 유기물층은 정공 차단층을 포함하고, 상기 정공 차단층은 상기 화학식 1로 표시되는 화합물을 포함한다. In the exemplary embodiment of the present specification, the organic material layer includes a hole blocking layer, and the hole blocking layer includes a compound represented by Formula 1 above.

본 명세서의 일 실시상태에 있어서, 상기 유기 발광 소자는 정공 주입층, 정공 수송층. 발광층, 전자 수송층, 전자 주입층, 정공 차단층 및 전자 차단층으로 이루어진 군에서 선택되는 1층 또는 2층 이상을 더 포함한다.In the exemplary embodiment of the present specification, the organic light emitting device is a hole injection layer and a hole transport layer. It further includes one or two or more layers selected from the group consisting of a light-emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer.

본 명세서의 일 실시상태에 있어서, 상기 발광층은 호스트 화합물을 더 포함한다.In the exemplary embodiment of the present specification, the emission layer further includes a host compound.

본 명세서의 일 실시상태에 있어서, 상기 발광층은 호스트 화합물을 더 포함하고, 상기 호스트 화합물은 적어도 하나의 수소가 중수소로 치환된 것이다.In the exemplary embodiment of the present specification, the emission layer further includes a host compound, and the host compound is one in which at least one hydrogen is substituted with deuterium.

본 명세서의 일 실시상태에 있어서, 상기 호스트 화합물이 중수소로 치환된 경우, 중수소로 30% 이상 치환된다. 또 다른 일 실시상태에 있어서, 상기 호스트 화합물은 중수소로 40% 이상 치환된다. 또 다른 일 실시상태에 있어서, 상기 호스트 화합물은 중수소로 60% 이상 치환된다. 또 다른 일 실시상태에 있어서, 상기 호스트 화합물은 중수소로 80% 이상 치환된다. 또 다른 일 실시상태에 있어서, 상기 호스트 화합물은 중수소로 100% 치환된다.In the exemplary embodiment of the present specification, when the host compound is substituted with deuterium, 30% or more is substituted with deuterium. In another exemplary embodiment, the host compound is substituted by 40% or more with deuterium. In another exemplary embodiment, the host compound is substituted with deuterium by at least 60%. In another exemplary embodiment, the host compound is 80% or more substituted with deuterium. In another exemplary embodiment, the host compound is 100% substituted with deuterium.

본 명세서의 일 실시상태에 있어서, 상기 발광층은 하기 화학식 H로 표시되는 화합물을 더 포함한다.In the exemplary embodiment of the present specification, the emission layer further includes a compound represented by the following formula (H).

[화학식 H][Formula H]

Figure PCTKR2020012249-appb-I000097
Figure PCTKR2020012249-appb-I000097

상기 화학식 H에 있어서,In Formula H,

L20 및 L21은 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 2가의 헤테로고리기이고,L20 and L21 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,

Ar20 및 Ar21은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이고,Ar20 and Ar21 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R20은 수소; 중수소; 할로겐기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이고,R20 is hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

r20은 0 내지 8의 정수이며, r20이 2이상인 경우, R20은 서로 동일하거나 상이하다.r20 is an integer from 0 to 8, and when r20 is 2 or more, R20 is the same as or different from each other.

본 명세서의 일 실시상태에 있어서, L20 및 L21은 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 탄소수 6 내지 40의 아릴렌기; 또는 탄소수 6 내지 40의 2가의 헤테로고리기이다.In the exemplary embodiment of the present specification, L20 and L21 are the same as or different from each other, and each independently a direct bond; An arylene group having 6 to 40 carbon atoms; Or it is a C6-C40 divalent heterocyclic group.

본 명세서의 일 실시상태에 있어서, L20 및 L21은 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 탄소수 6 내지 20의 아릴렌기; 또는 탄소수 6 내지 20의 2가의 헤테로고리기이다.In the exemplary embodiment of the present specification, L20 and L21 are the same as or different from each other, and each independently a direct bond; An arylene group having 6 to 20 carbon atoms; Or a divalent heterocyclic group having 6 to 20 carbon atoms.

본 명세서의 일 실시상태에 있어서, L20 및 L21은 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 페닐렌기; 비페닐렌기; 나프틸렌기; 2가의 디벤조퓨란기; 또는 2가의 디벤조티오펜기이다.In the exemplary embodiment of the present specification, L20 and L21 are the same as or different from each other, and each independently a direct bond; Phenylene group; Biphenylene group; Naphthylene group; Divalent dibenzofuran group; Or a divalent dibenzothiophene group.

본 명세서의 일 실시상태에 있어서, Ar20 및 Ar21은 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 60의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 60의 헤테로고리기이다.In the exemplary embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C2 to C60 heterocyclic group.

본 명세서의 일 실시상태에 있어서, Ar20 및 Ar21은 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 헤테로고리기이다.In the exemplary embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heterocyclic group.

본 명세서의 일 실시상태에 있어서, Ar20 및 Ar21은 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 단환 내지 4환의 아릴기; 또는 치환 또는 비치환된 단환 내지 4환의 헤테로고리기이다.In the exemplary embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic to tetracyclic aryl group; Or a substituted or unsubstituted monocyclic to 4 ring heterocyclic group.

본 명세서의 일 실시상태에 있어서, Ar20 및 Ar21은 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 페닐기; 치환 또는 비치환된 비페닐기; 치환 또는 비치환된 터페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 안트라센기; 치환 또는 비치환된 페난트릴기; 치환 또는 비치환된 페날렌기; 치환 또는 비치환된 플루오레닐기; 치환 또는 비치환된 벤조플루오레닐기; 치환 또는 비치환된 퓨란기; 치환 또는 비치환된 티오펜기; 치환 또는 비치환된 디벤조퓨란기; 치환 또는 비치환된 나프토벤조퓨란기; 치환 또는 비치환된 디벤조티오펜기; 또는 치환 또는 비치환된 나프토벤조티오펜기이다.In the exemplary embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted anthracene group; A substituted or unsubstituted phenanthryl group; A substituted or unsubstituted phenalene group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted benzofluorenyl group; A substituted or unsubstituted furan group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted naphthobenzofuran group; A substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted naphthobenzothiophene group.

본 명세서의 일 실시상태에 있어서, Ar20 및 Ar21은 서로 동일하거나 상이하고, 각각 독립적으로 탄소수 6 내지 20의 아릴기로 치환 또는 비치환된 페닐기; 탄소수 6 내지 20의 아릴기로 치환 또는 비치환된 비페닐기; 탄소수 6 내지 20의 아릴기로 치환 또는 비치환된 나프틸기; 탄소수 6 내지 20의 아릴기로 치환 또는 비치환된 디벤조퓨란기; 탄소수 6 내지 20의 아릴기로 치환 또는 비치환된 나프토벤조퓨란기; 탄소수 6 내지 20의 아릴기로 치환 또는 비치환된 디벤조티오펜기; 또는 탄소수 6 내지 20의 아릴기로 치환 또는 비치환된 나프토벤조티오펜기이다.In the exemplary embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms; A biphenyl group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms; A naphthyl group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms; A dibenzofuran group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms; A naphthobenzofuran group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms; A dibenzothiophene group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms; Or a naphthobenzothiophene group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms.

본 명세서의 일 실시상태에 있어서, Ar20은 치환 또는 비치환된 헤테로고리기이고, Ar21은 치환 또는 비치환된 아릴기이다.In the exemplary embodiment of the present specification, Ar20 is a substituted or unsubstituted heterocyclic group, and Ar21 is a substituted or unsubstituted aryl group.

본 명세서의 일 실시상태에 있어서, Ar20 및 Ar21은 서로 동일하거나 상이하고, 각각 독립적으로 중수소로 치환 또는 비치환된 페닐기; 중수소로 치환 또는 비치환된 나프틸기; 또는 중수소로 치환 또는 비치환된 디벤조퓨란기이다.In the exemplary embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with deuterium; A naphthyl group unsubstituted or substituted with deuterium; Or a dibenzofuran group unsubstituted or substituted with deuterium.

본 명세서의 일 실시상태에 있어서, R20은 수소; 중수소; 할로겐기; 치환 또는 비치환된 탄소수 1 내지 30의 알킬기; 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기; 치환 또는 비치환된 탄소수 6 내지 60의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 60의 헤테로아릴기이다.In an exemplary embodiment of the present specification, R20 is hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted C1-C30 alkyl group; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C2 to C60 heteroaryl group.

본 명세서의 일 실시상태에 있어서, R20은 수소; 중수소; 불소기; 치환 또는 비치환된 탄소수 1 내지 10의 알킬기; 치환 또는 비치환된 탄소수 3 내지 10의 시클로알킬기; 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 헤테로아릴기이다.In an exemplary embodiment of the present specification, R20 is hydrogen; heavy hydrogen; Fluorine group; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted C 3 to C 10 cycloalkyl group; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heteroaryl group.

본 명세서의 일 실시상태에 있어서, R20은 수소; 중수소; 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 헤테로아릴기이다.In an exemplary embodiment of the present specification, R20 is hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heteroaryl group.

본 명세서의 일 실시상태에 있어서, R20은 수소; 중수소; 치환 또는 비치환된 페닐기; 치환 또는 비치환 나프틸기; 치환 또는 비치환된 디벤조퓨란기; 또는 치환 또는 비치환된 디벤조티오펜기이다.In an exemplary embodiment of the present specification, R20 is hydrogen; heavy hydrogen; A substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group.

본 명세서의 일 실시상태에 있어서, R20은 수소; 중수소; 또는 중수소로 치환 또는 비치환된 나프틸기이다.In an exemplary embodiment of the present specification, R20 is hydrogen; heavy hydrogen; Or a naphthyl group unsubstituted or substituted with deuterium.

본 명세서의 일 실시상태에 있어서, r20은 1 내지 8의 정수이다.In an exemplary embodiment of the present specification, r20 is an integer of 1 to 8.

본 명세서의 일 실시상태에 있어서, 상기 화학식 H는 적어도 하나의 중수소를 포함할 수 있다.In the exemplary embodiment of the present specification, Chemical Formula H may include at least one deuterium.

본 명세서의 일 실시상태에 있어서, 상기 화학식 H는 하기 화학식 I 또는 J로 표시된다.In an exemplary embodiment of the present specification, Chemical Formula H is represented by the following Chemical Formula I or J.

[화학식 I][Formula I]

Figure PCTKR2020012249-appb-I000098
Figure PCTKR2020012249-appb-I000098

[화학식 J][Formula J]

Figure PCTKR2020012249-appb-I000099
Figure PCTKR2020012249-appb-I000099

상기 화학식 I 및 J에서, 치환기들의 정의는 화학식 H에서의 정의와 같다.In Formulas I and J, the definitions of substituents are the same as those in Formula H.

본 명세서의 일 실시상태에 있어서, 상기 화학식 H로 표시되는 화합물이 중수소로 치환된 경우, 중수소로 30% 이상 치환된다. 또 다른 일 실시상태에 있어서, 상기 화학식 H의 구조는 중수소로 40% 이상 치환된다. 또 다른 일 실시상태에 있어서, 상기 화학식 H의 구조는 중수소로 60% 이상 치환된다. 또 다른 일 실시상태에 있어서, 상기 화학식 H의 구조는 중수소로 80% 이상 치환된다. 또 다른 일 실시상태에 있어서, 상기 화학식 H의 구조는 중수소로 100% 치환된다.In the exemplary embodiment of the present specification, when the compound represented by Formula H is substituted with deuterium, 30% or more is substituted with deuterium. In another exemplary embodiment, the structure of Formula H is substituted by 40% or more with deuterium. In another exemplary embodiment, the structure of Formula H is substituted with deuterium by at least 60%. In another exemplary embodiment, the structure of Formula H is substituted with deuterium by 80% or more. In another exemplary embodiment, the structure of Formula H is 100% substituted with deuterium.

본 명세서의 일 실시상태에 있어서, 상기 화학식 H로 표시되는 화합물은 하기 화합물 중에서 선택되는 어느 하나이다. In the exemplary embodiment of the present specification, the compound represented by Formula H is any one selected from the following compounds.

Figure PCTKR2020012249-appb-I000100
Figure PCTKR2020012249-appb-I000100

Figure PCTKR2020012249-appb-I000101
Figure PCTKR2020012249-appb-I000101

Figure PCTKR2020012249-appb-I000102
Figure PCTKR2020012249-appb-I000102

본 명세서의 일 실시상태에 있어서, 상기 발광층에서 화학식 1로 표시되는 화합물은 도펀트로, 상기 화학식 H로 표시되는 화합물은 호스트로 사용된다. In the exemplary embodiment of the present specification, in the emission layer, the compound represented by Formula 1 is used as a dopant, and the compound represented by Formula H is used as a host.

본 명세서의 일 실시상태에 있어서, 상기 발광층이 호스트 및 도펀트를 포함할 경우, 도펀트의 함량은 호스트 100 중량부를 기준으로 0.01 내지 10 중량부의 범위에서 선택될 수 있으며, 이에 한정되지 않는다.In the exemplary embodiment of the present specification, when the emission layer includes a host and a dopant, the content of the dopant may be selected from 0.01 to 10 parts by weight based on 100 parts by weight of the host, but is not limited thereto.

본 명세서의 일 실시상태에 있어서, 상기 발광층은 2종 이상의 호스트 화합물을 더 포함한다. 상기 발광층이 2종의 호스트를 포함할 경우, 호스트의 함량은 제1 호스트:제2 호스트 기준 10:90 내지 90:10일 수 있다. 일 예에 있어서, 상기 호스트 간의 함량은 20:80 내지 80:20일 수 있으며, 다른 일 예에 있어서, 40:60 내지 60:40일 수 있다.In the exemplary embodiment of the present specification, the emission layer further includes two or more host compounds. When the emission layer includes two types of hosts, the content of the host may be 10:90 to 90:10 based on a first host: a second host. In one example, the content between the hosts may be 20:80 to 80:20, and in another example, it may be 40:60 to 60:40.

상기 발광층은 호스트 재료를 더 포함할 수 있고, 상기 호스트는 축합 방향족환 유도체 또는 헤테로환 함유 화합물 등이 있다. 구체적으로 축합 방향족환 유도체로는 안트라센 유도체, 피렌 유도체, 나프탈렌 유도체, 펜타센 유도체, 페난트렌 화합물, 플루오란텐 화합물 등이 있고, 헤테로환 함유 화합물로는 카바졸 유도체, 디벤조퓨란 유도체, 래더형 퓨란 화합물, 피리미딘 유도체 또는 트리아진 유도체 등이 있으며, 이들의 2 종 이상의 혼합물일 수 있으나, 이에 한정되지 않는다. The light-emitting layer may further include a host material, and the host may include a condensed aromatic ring derivative or a heterocyclic-containing compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, triazine derivatives, and the like, and may be a mixture of two or more thereof, but are not limited thereto.

본 명세서의 일 실시상태에 있어서, 상기 유기 발광 소자는 제1 전극; 제2 전극; 상기 제1 전극과 상기 제2 전극 사이에 구비된 발광층; 및 상기 발광층과 상기 제1 전극 사이, 또는 상기 발광층과 상기 제2 전극 사이에 구비된 2층 이상의 유기물층을 포함하고, 상기 2층 이상의 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함한다. In one embodiment of the present specification, the organic light emitting device includes a first electrode; A second electrode; A light emitting layer provided between the first electrode and the second electrode; And two or more organic material layers provided between the light-emitting layer and the first electrode or between the light-emitting layer and the second electrode, and at least one of the two or more organic material layers includes a compound represented by Formula 1 above.

본 명세서의 일 실시상태에 있어서, 상기 2층 이상의 유기물층은 발광층, 정공 수송층, 정공 주입층, 정공 수송과 정공 주입을 동시에 하는 층 및 전자 차단층으로 이루어진 군에서 2 이상이 선택될 수 있다.In the exemplary embodiment of the present specification, two or more organic material layers may be selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, a layer for simultaneously transporting and injecting holes, and an electron blocking layer.

본 명세서의 일 실시상태에 있어서, 상기 유기물층은 2층 이상의 전자 수 송층을 포함하고, 상기 2층 이상의 전자 수송층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함한다. 구체적으로 본 명세서의 일 실시상태에 있어서, 상기 화학식 1로 표시되는 화합물은 상기 2층 이상의 전자 수송층 중 1층에 포함될 수도 있으며, 각각의 2층 이상의 전자 수송층에 포함될 수 있다. In the exemplary embodiment of the present specification, the organic material layer includes two or more electron transport layers, and at least one of the two or more electron transport layers includes a compound represented by Formula 1 above. Specifically, in the exemplary embodiment of the present specification, the compound represented by Formula 1 may be included in one of the two or more electron transport layers, and may be included in each of two or more electron transport layers.

또한, 본 명세서의 일 실시상태에 있어서, 상기 화합물이 상기 각각의 2층 이상의 전자 수송층에 포함되는 경우, 상기 화학식 1로 표시되는 화합물을 제외한 다른 재료들은 서로 동일하거나 상이할 수 있다.In addition, in the exemplary embodiment of the present specification, when the compound is included in each of the two or more electron transport layers, materials other than the compound represented by Formula 1 may be the same or different from each other.

상기 화학식 1로 표시되는 화합물을 포함하는 유기물층이 전자 수송층인 경우, 상기 전자 수송층은 n형 도펀트를 더 포함할 수 있다. 상기 n형 도펀트는 당 기술분야에 알려져 있는 것들을 사용할 수 있으며, 예컨대 금속 또는 금속착체를 사용할 수 있다. 예를 들어, 상기 화학식 1로 표시되는 화합물을 포함하는 전자 수송층은 LiQ(Lithium Quinolate)를 더 포함할 수 있다.When the organic material layer including the compound represented by Formula 1 is an electron transport layer, the electron transport layer may further include an n-type dopant. As the n-type dopant, those known in the art may be used, for example, a metal or a metal complex. For example, the electron transport layer including the compound represented by Formula 1 may further include LiQ (Lithium Quinolate).

본 명세서의 일 실시상태에 있어서, 상기 유기물층은 2층 이상의 정공수송층을 포함하고, 상기 2층 이상의 정공 수송층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함한다. 구체적으로, 본 명세서의 일 실시상태에 있어서, 상기 화학식 1로 표시되는 화합물은 상기 2층 이상의 정공 수송층 중 1층에 포함될 수도 있으며, 각각의 2층 이상의 정공 수송층에 포함될 수 있다. In the exemplary embodiment of the present specification, the organic material layer includes two or more hole transport layers, and at least one of the two or more hole transport layers includes a compound represented by Formula 1 above. Specifically, in the exemplary embodiment of the present specification, the compound represented by Formula 1 may be included in one of the two or more hole transport layers, and may be included in each of two or more hole transport layers.

또한, 본 명세서의 일 실시상태에 있어서, 상기 화학식 1로 표시되는 화합물이 상기 각각의 2층 이상의 정공 수송층에 포함되는 경우, 상기 화학식 1로 표시되는 화합물을 제외한 다른 재료들은 서로 동일하거나 상이할 수 있다.In addition, in the exemplary embodiment of the present specification, when the compound represented by Formula 1 is included in each of the two or more hole transport layers, materials other than the compound represented by Formula 1 may be the same or different from each other. have.

본 명세서의 일 실시상태에 있어서, 상기 유기물층은 상기 화학식 1로 표시되는 화합물을 포함하는 유기물층 이외에 아릴아민기, 카바졸릴기 또는 벤조카바졸릴기를 포함하는 화합물을 포함하는 정공 주입층 또는 정공 수송층을 더 포함할 수 있다.In the exemplary embodiment of the present specification, the organic material layer further comprises a hole injection layer or a hole transport layer including a compound including an arylamine group, a carbazolyl group, or a benzocarbazolyl group in addition to the organic material layer including the compound represented by Formula 1 Can include.

본 명세서의 일 실시상태에 있어서, 상기 제1 전극은 애노드 또는 캐소드이다.In the exemplary embodiment of the present specification, the first electrode is an anode or a cathode.

본 명세서의 일 실시상태에 있어서, 상기 제2 전극은 캐소드 또는 애노드이다. In the exemplary embodiment of the present specification, the second electrode is a cathode or an anode.

본 명세서의 일 실시상태에 있어서, 상기 유기 발광 소자는 기판 상에 애노드, 1층 이상의 유기물층 및 캐소드가 순차적으로 적층된 구조(normal type)의 유기 발광 소자일 수 있다. In the exemplary embodiment of the present specification, the organic light-emitting device may be a normal type organic light-emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

본 명세서의 일 실시상태에 있어서, 상기 유기 발광 소자는 기판 상에 캐소드, 1층 이상의 유기물층 및 애노드가 순차적으로 적층된 역방향 구조(inverted type)의 유기 발광 소자일 수 있다.In the exemplary embodiment of the present specification, the organic light emitting device may be an inverted type organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.

예컨대, 본 명세서의 일 실시상태에 따른 유기 발광 소자의 구조가 도 1 및 도 2에 예시되어 있다. 상기 도 1 및 도 2은 유기 발광 소자를 예시한 것이며 이에 한정되는 것은 아니다. For example, the structure of an organic light-emitting device according to an exemplary embodiment of the present specification is illustrated in FIGS. 1 and 2. 1 and 2 illustrate an organic light-emitting device and are not limited thereto.

도 1은 기판(1), 양극(2), 발광층(7) 및 음극(11)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서, 상기 화합물은 상기 발광층(3)에 포함될 수 있다. 1 illustrates a structure of an organic light-emitting device in which a substrate 1, an anode 2, an emission layer 7 and a cathode 11 are sequentially stacked. In such a structure, the compound may be included in the emission layer 3.

도 2는 기판(1), 양극(2), 제1 정공주입층(3), 제2 정공주입층(4), 정공수송층(5), 전자차단층(6), 발광층(7), 제1 전자수송층(8), 제2 전자수송층(9), 전자주입층(10) 및 음극(11)이 순차적으로 적층된 유기 발광 소자의 예를 도시한 것이다. 이와 같은 구조에 있어서 상기 화합물은 상기 제1 정공주입층(3), 제2 정공주입층(4), 정공수송층(5), 전자차단층(6), 발광층(7), 제1 전자수송층(8), 제2 전자수송층(9) 및 전자주입층(10) 중 1층 이상에 포함될 수 있다.2 shows a substrate 1, an anode 2, a first hole injection layer 3, a second hole injection layer 4, a hole transport layer 5, an electron blocking layer 6, a light emitting layer 7, and An example of an organic light-emitting device in which the first electron transport layer 8, the second electron transport layer 9, the electron injection layer 10, and the cathode 11 are sequentially stacked is shown. In such a structure, the compound includes the first hole injection layer 3, the second hole injection layer 4, the hole transport layer 5, the electron blocking layer 6, the light emitting layer 7, and the first electron transport layer ( 8), it may be included in one or more of the second electron transport layer 9 and the electron injection layer 10.

본 명세서의 유기 발광 소자는 유기물층 중 1층 이상이 상기 화합물, 즉 상기 화학식 1로 표시되는 화합물을 포함하는 것을 제외하고는 당 기술분야에 알려져 있는 재료와 방법으로 제조될 수 있다. The organic light-emitting device of the present specification may be manufactured by materials and methods known in the art, except that at least one of the organic material layers includes the compound, that is, the compound represented by Formula 1.

상기 유기 발광 소자가 복수개의 유기물층을 포함하는 경우, 상기 유기물층은 동일한 물질 또는 다른 물질로 형성될 수 있다. When the organic light-emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

예컨대, 본 명세서의 유기 발광 소자는 기판 상에 제1 전극, 유기물층 및 제2 전극을 순차적으로 적층시킴으로써 제조할 수 있다. 이 때, 스퍼터링법(sputtering)이나 전자빔 증발법(e-beam evaporation)과 같은 PVD(physical Vapor Deposition)방법을 이용하여, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극을 형성하고, 그 위에 정공 주입층, 정공 수송층, 발광층 및 전자 수송층을 포함하는 유기물층을 형성한 후, 그 위에 캐소드로 사용할 수 있는 물질을 증착시킴으로써 제조될 수 있다. 이와 같은 방법 외에도, 기판 상에 캐소드 물질, 유기물층 및 애노드 물질을 차례로 증착시켜 유기 발광 소자를 제조할 수 있다. For example, the organic light emitting device of the present specification may be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, a metal or a conductive metal oxide or an alloy thereof is deposited on the substrate to form an anode. It can be manufactured by forming and forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

또한, 상기 화학식 1로 표시되는 화합물은 유기 발광 소자의 제조시 진공 증착법 뿐만 아니라 용액 도포법에 의하여 유기물층으로 형성될 수 있다. 여기서, 용액 도포법이라 함은 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯프린팅, 스크린 프린팅, 스프레이법, 롤 코팅 등을 의미하나, 이에 한정되는 것은 아니다. In addition, the compound represented by Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.

이와 같은 방법 외에도, 기판 상에 음극 물질로부터 유기물층, 양극 물질을 차례로 증착시켜 유기 발광 소자를 만들 수도 있다 (국제 특허 출원 공개 제 2003/012890호). 다만, 제조 방법이 이에 한정되는 것은 아니다. In addition to such a method, an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate (International Patent Application Publication No. 2003/012890). However, the manufacturing method is not limited thereto.

상기 제1 전극 물질로는 통상 유기물층으로 정공 주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 예를 들어, 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연 산화물, 인듐 산화물, 인듐주석 산화물(ITO), 인듐아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SnO2 : Sb와 같은 금속과 산화물의 조합; 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDOT), 폴리피롤 및 폴리아닐린과 같은 전도성 고분자 등이 있으나, 이에 한정되는 것은 아니다. As the first electrode material, a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer. For example, metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of a metal and an oxide such as ZnO:Al or SnO 2 :Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

상기 제2 전극 물질로는 통상 유기물층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 예를 들어, 마그네슘, 칼슘, 나트륨, 칼륨, 티타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석 및 납과 같은 금속 또는 이들의 합금; LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있으나, 이에 한정되는 것은 아니다.The second electrode material is generally preferably a material having a small work function so that electrons can be easily injected into the organic material layer. Metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; There are a multi-layered material such as LiF/Al or LiO 2 /Al, but are not limited thereto.

상기 발광층은 호스트 재료 및 도펀트 재료를 포함할 수 있다. 호스트 재료로는 축합 방향족환 유도체 또는 헤테로환 함유 화합물 등이 있다. 구체적으로, 축합 방향족환 유도체로는 안트라센 유도체, 피렌 유도체, 나프탈렌 유도체, 펜타센 유도체, 페난트렌 화합물, 플루오란텐 화합물 등이 있고, 헤테로환 함유 화합물로는 디벤조퓨란 유도체, 래더형 퓨란 화합물, 피리미딘 유도체 등이 있으나, 이에 한정되는 것은 아니다. The emission layer may include a host material and a dopant material. Examples of the host material include condensed aromatic ring derivatives or heterocyclic-containing compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include dibenzofuran derivatives, ladder furan compounds, And pyrimidine derivatives, but are not limited thereto.

상기 도펀트 재료로는 상기 화학식 1로 표시되는 화합물 이외에 방향족 아민 유도체, 스트릴아민 화합물, 붕소 착체, 플루오란텐 화합물, 금속 착체 등이 있다. 구체적으로, 방향족 아민 유도체로는 치환 또는 비치환된 아릴아민기를 갖는 축합 방향족환 유도체로서, 아릴아민기를 갖는 피렌, 안트라센, 크리센, 페리플란텐 등이 있다. 또한, 스티릴아민 화합물은 치환 또는 비치환된 아릴아민에 적어도 1개의 아릴비닐기가 치환되어 있는 화합물로, 아릴기, 실릴기, 알킬기, 시클로알킬기 및 아릴아민기로 이루어진 군에서 1 또는 2 이상 선택되는 치환기가 치환 또는 비치환된다. 구체적으로 스티릴아민, 스티릴디아민, 스티릴트리아민, 스티릴테트라아민 등이 있으나, 이에 한정되지 않는다. 또한, 금속 착체로는 이리듐 착체, 백금 착체 등이 있으나, 이에 한정되는 것은 아니다. Examples of the dopant material include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes in addition to the compound represented by Formula 1 above. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamine group, and includes pyrene, anthracene, chrysene, periflanthene and the like having an arylamine group. In addition, the styrylamine compound is a compound in which at least one arylvinyl group is substituted with a substituted or unsubstituted arylamine, and is selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group. Substituents are substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, and styryltetraamine, but are not limited thereto. In addition, examples of the metal complex include an iridium complex and a platinum complex, but are not limited thereto.

본 명세서에서, 상기 화학식 1로 표시되는 화합물이 발광층 이외의 유기물층에 포함되거나, 추가의 발광층이 구비되는 경우, 상기 발광층의 발광 물질로는 정공 수송층과 전자 수송층으로부터 정공과 전자를 각각 수송 받아 결합시킴으로써 가시광선 영역의 빛을 낼 수 있는 물질로서, 형광이나 인광에 대한 양자 효율이 좋은 물질이 바람직하다. 예를 들어, 8-히드록시-퀴놀린 알루미늄 착물(Alq3); 카르바졸 계열 화합물; 이량체화 스티릴(dimerized styryl) 화합물; BAlq; 10-히드록시벤조 퀴놀린-금속 화합물; 벤족사졸, 벤즈티아졸 및 벤즈이미다졸 계열의 화합물; 폴리(p-페닐렌비닐렌)(PPV) 계열의 고분자; 스피로(spiro) 화합물; 폴리플루오렌; 및 루브렌 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, when the compound represented by Formula 1 is included in an organic material layer other than the emission layer or an additional emission layer is provided, the emission material of the emission layer is formed by transporting and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively. As a material capable of emitting light in the visible region, a material having good quantum efficiency for fluorescence or phosphorescence is preferable. For example, 8-hydroxy-quinoline aluminum complex (Alq3); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole, and benzimidazole-based compounds; Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene; And rubrene, but are not limited thereto.

상기 정공 주입층은 전극으로부터 정공을 주입하는 층이다. 정공 주입 물질은 정공을 수송하는 능력을 가져 제1 전극에서의 정공 주입 효과 및 발광층 또는 발광 재료에 대하여 우수한 정공 주입 효과를 갖는 것이 바람직하다. 또한, 발광층에서 생성된 여기자의 전자 주입층 또는 전자 주입 재료에의 이동을 방지할 수 있는 능력이 우수한 물질이 바람직하다. 또한, 박막 형성 능력이 우수한 물질이 바람직하다. 또한, 정공 주입 물질의 HOMO(highest occupied molecular orbital)가 제1 전극 물질의 일함수와 주변 유기물층의 HOMO 사이인 것이 바람직하다. 정공 주입 물질의 구체적인 예로는, 금속 포피린(porphyrin), 올리고티오펜, 아릴아민 계열의 유기물; 카르바졸 계열의 유기물; 니트릴 계열의 유기물; 헥사니트릴헥사아자트리페닐렌 계열의 유기물; 퀴나크리돈(quinacridone)계열의 유기물; 페릴렌(perylene) 계열의 유기물; 안트라퀴논, 폴리아닐린과 같은 폴리티오펜 계열의 전도성 고분자 등 또는 상기 예 중 2 이상을 혼합물 등이 있으나, 이에 한정 되는 것은 아니다. The hole injection layer is a layer for injecting holes from an electrode. It is preferable that the hole injection material has the ability to transport holes and thus has a hole injection effect in the first electrode and an excellent hole injection effect in the light emitting layer or the light emitting material. In addition, a material having excellent ability to prevent movement of excitons generated in the light emitting layer to the electron injection layer or the electron injection material is preferable. In addition, a material excellent in thin film formation ability is preferred. In addition, it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the first electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material; Carbazole-based organic matter; Nitrile-based organics; Hexanitrile hexaazatriphenylene-based organic material; Quinacridone series organic matter; Perylene-based organics; Polythiophene-based conductive polymers such as anthraquinone and polyaniline, or a mixture of two or more of the above examples, but are not limited thereto.

상기 정공 수송층은 정공 주입층으로부터 정공을 수취하여 발광층까지 정공을 수송하는 층이다. 정공 수송 물질로는 제1 전극이나 정공 주입층으로부터 정공을 수송받아 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 바람직하다. 구체적인 예로는, 아릴아민 계열의 유기물, 카르바졸 계열의 유기물, 전도성 고분자, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나, 이에 한정되는 것은 아니다.The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the emission layer. The hole transporting material is a material capable of transporting holes from the first electrode or the hole injection layer and transferring them to the light emitting layer, and a material having high mobility for holes is preferable. Specific examples include, but are not limited to, an arylamine-based organic material, a carbazole-based organic material, a conductive polymer, and a block copolymer including a conjugated portion and a non-conjugated portion.

상기 전자 수송층은 전자 주입층으로부터 전자를 수취하여 발광층까지 전자를 수송하는 층이다. 전자 수송 물질로는 제2 전극으로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서, 전자에 대한 이동성이 큰 물질이 바람직하다. 구체적인 예로는, 8-히드록시퀴놀린의 Al착물; Alq3를 포함한 착물; 유기 라디칼 화합물; 히드록시플라본-금속 착물; 트리아진 유도체; LiQ 등이 있으나, 이에 한정되는 것은 아니다. 전자 수송층은 종래기술에 따라 사용된 바와 같이, 임의의 원하는 제1 전극 물질과 함께 사용할 수 있다. 특히, 적절한 제1 전극 물질은 낮은 일함수를 가지며, 알루미늄층 또는 실버층이 뒤따르는 통상적인 물질이다. 구체적으로, 세슘, 바륨, 칼슘, 이테르븀 및 사마륨 등이 있고, 각 경우 알루미늄층 또는 실버층이 뒤따른다.The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. The electron transport material is a material capable of receiving electrons from the second electrode and transferring them to the light emitting layer, and a material having high mobility for electrons is preferable. Specific examples include Al complex of 8-hydroxyquinoline; Complexes containing Alq3; Organic radical compounds; Hydroxyflavone-metal complex; Triazine derivatives; LiQ and the like, but are not limited thereto. The electron transport layer can be used with any desired first electrode material, as used according to the prior art. In particular, a suitable first electrode material has a low work function and is a conventional material followed by an aluminum layer or a silver layer. Specifically, there are cesium, barium, calcium, ytterbium and samarium, and in each case, an aluminum layer or a silver layer follows.

상기 전자 주입층은 전극으로부터 전자를 주입하는 층이다. 전자 주입물로는 전자를 수송하는 능력이 우수하고, 제2 전극으로부터의 전자 주입 효과, 발광층 또는 발광 재료에 대하여 우수한 전자주입 효과를 갖는 것이 바람직하다. 또한, 발광층에서 생성된 여기자가 정공 주입층으로 이동하는 것을 방지하고, 박막 형성 능력이 우수한 물질이 바람직하다. 구체적으로는, 플루오레논, 안트라퀴노다이메탄, 다이페노퀴논, 티오피란 다이옥사이드, 옥사졸, 옥사다이아졸, 트리아졸, 트리아진, 이미다졸, 페릴렌테트라카복실산, 프레오레닐리덴 메탄, 안트론 등과 그들의 유도체, 금속 착체 화합물 및 함질소 5원환 유도체, 상기 예 중 2 이상의 혼합물 등이 있으나, 이에 한정되는 것은 아니다. The electron injection layer is a layer that injects electrons from an electrode. It is preferable that the electron injection material is excellent in the ability to transport electrons, and has an electron injection effect from the second electrode and an excellent electron injection effect on the light-emitting layer or the light-emitting material. In addition, a material that prevents excitons generated in the light emitting layer from moving to the hole injection layer and has excellent thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, triazine, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc. Derivatives thereof, metal complex compounds and nitrogen-containing 5-membered ring derivatives, and mixtures of two or more of the above examples, but are not limited thereto.

상기 금속 착체 화합물로는 8-하이드록시퀴놀리나토 리튬, 비스(8-하이드록시퀴놀리나토)아연, 비스(8-하이드록시퀴놀리나토)구리, 비스(8-하이드록시퀴놀리나토)망간, 트리스(8-하이드록시퀴놀리나토)알루미늄, 트리스(2-메틸-8-하이드록시퀴놀리나토)알루미늄, 트리스(8-하이드록시퀴놀리나토)갈륨, 비스(10-하이드록시벤조[h]퀴놀리나토)베릴륨, 비스(10-하이드록시벤조[h]퀴놀리나토)아연, 비스(2-메틸-8-퀴놀리나토)클로로갈륨, 비스(2-메틸-8-퀴놀리나토)(o-크레졸라토)갈륨, 비스(2-메틸-8-퀴놀리나토)(1-나프톨라토)알루미늄, 비스(2-메틸-8-퀴놀리나토)(2-나프톨라토)갈륨 등이 있으나, 이에 한정되는 것은 아니다.As the metal complex compound, 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese , Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h) ]Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato) (o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc. , But is not limited thereto.

상기 전자 차단층은 정공 주입층으로부터 주입된 정공이 발광층을 지나 전자 주입층으로 진입하는 것을 방지하여 소자의 수명과 효율을 향상시킬 수 있는 층이다. 공지된 재료는 제한 없이 사용 가능하며, 발광층과 정공 주입층 사이에, 또는 발광층과 정공 주입 및 정공 수송을 동시에 하는 층 사이에 형성될 수 있다. The electron blocking layer is a layer capable of improving the lifespan and efficiency of a device by preventing holes injected from the hole injection layer from entering the electron injection layer through the emission layer. Known materials may be used without limitation, and may be formed between the light-emitting layer and the hole injection layer, or between the light-emitting layer and a layer that simultaneously injects and transports holes.

상기 정공 차단층은 정공의 제2 전극으로 도달을 저지하는 층으로, 일반적으로 정공 주입층과 동일한 조건으로 형성될 수 있다. 구체적으로, 옥사디아졸 유도체나 트리아졸 유도체, 페난트롤린 유도체, 알루미늄 착물 (aluminum complex), 피리딘, 피리미딘 또는 트리아진 유도체 등이 있으나, 이에 한정되는 것은 아니다.The hole blocking layer is a layer that prevents holes from reaching the second electrode, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, aluminum complexes, pyridine, pyrimidine or triazine derivatives, but are not limited thereto.

본 명세서에 따른 유기 발광 소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.The organic light-emitting device according to the present specification may be a top emission type, a bottom emission type, or a double-sided emission type depending on the material used.

본 명세서의 일 실시상태에 있어서, 상기 화학식 1로 표시되는 화합물은 유기 발광 소자 외에도 유기 태양 전지 또는 유기 트랜지스터에 포함될 수 있다.In the exemplary embodiment of the present specification, the compound represented by Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.

본 명세서에 따른 화합물은 유기 인광 소자, 유기 태양 전지, 유기 감광체, 유기 트랜지스터 등을 비롯한 유기 발광 소자에서도 유기 발광 소자에 적용되는 것과 유사한 원리로 작용할 수 있다. 예컨대, 상기 유기 태양 전지는 음극, 양극 및 상기 음극과 양극 사이에 구비된 광활성층을 포함하는 구조일 수 있고, 상기 광활성층은 상기 화합물을 포함할 수 있다.The compound according to the present specification may act on a principle similar to that applied to an organic light-emitting device in an organic light-emitting device including an organic phosphorescent device, an organic solar cell, an organic photoreceptor, and an organic transistor. For example, the organic solar cell may have a structure including a negative electrode, a positive electrode, and a photoactive layer provided between the negative electrode and the positive electrode, and the photoactive layer may include the compound.

이하, 본 명세서를 구체적으로 설명하기 위해 실시예 및 비교예 등을 들어 상세하게 설명하기로 한다. 그러나, 본 명세서에 따른 실시예 및 비교예는 여러 가지 다른 형태로 변형될 수 있으며, 본 명세서의 범위가 아래에서 상술하는 실시예 및 비교예에 한정되는 것으로 해석되지 않는다. 본 명세서의 실시예 및 비교예는 당업계에서 평균적인 지식을 가진 자에게 본 명세서를 보다 완전하게 설명하기 위해 제공되는 것이다.Hereinafter, examples and comparative examples will be described in detail to describe the present specification in detail. However, the Examples and Comparative Examples according to the present specification may be modified in various forms, and the scope of the present specification is not construed as being limited to the Examples and Comparative Examples described below. Examples and comparative examples of the present specification are provided to more completely describe the present specification to those of ordinary skill in the art.

합성예 1. 화합물 1의 합성Synthesis Example 1. Synthesis of Compound 1

<1-a> 화합물 1-a의 제조<1-a> Preparation of compound 1-a

Figure PCTKR2020012249-appb-I000103
Figure PCTKR2020012249-appb-I000103

3구 플라스크에 1-브로모-3-클로로-5-(메틸-d3)벤젠 (1 eq.)과 5-터부틸-N-(4-터부틸페닐)-[1,1'-바이페닐]-2-아민 (1 eq.)을 톨루엔 (0.3 M)에 녹이고 소듐 터부톡사이드 (1.2 eq.), 비스(트리-터부틸포스핀)팔라듐(0) (0.01 eq.)을 넣은 후, 아르곤 분위기 환류 조건하에서 2시간 동안 교반하였다. 반응이 종료되면 상온으로 냉각한 후, H2O를 넣고 반응액을 분액 깔대기에 옮겨 추출하였다. 추출액을 MgSO4로 건조, 농축하고 시료를 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 1-a 를 수득하였다. (수율 82%, MS[M+H]+ = 486)In a 3-neck flask, 1-bromo-3-chloro-5-(methyl-d 3 )benzene (1 eq.) and 5-terbutyl-N-(4-terbutylphenyl)-[1,1'-bi Phenyl]-2-amine (1 eq.) is dissolved in toluene (0.3 M), sodium terbutoxide (1.2 eq.) and bis(tri-terbutylphosphine) palladium (0) (0.01 eq.) are added. , The mixture was stirred for 2 hours under reflux conditions in an argon atmosphere. When the reaction was completed, after cooling to room temperature, H 2 O was added and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO 4 , concentrated, and the sample was purified by silica gel column chromatography to obtain compound 1-a. (Yield 82%, MS[M+H] + = 486)

<1-b> 화합물 1-b의 제조<1-b> Preparation of compound 1-b

Figure PCTKR2020012249-appb-I000104
Figure PCTKR2020012249-appb-I000104

합성예 <1-a>와 동일한 방법으로, 1-a와 비스(4-(프로판-2-일-d7)페닐)아민로부터 1-b를 얻었다. (수율 86%, MS[M+H]+ = 717)In the same manner as in Synthesis Example <1-a>, 1-b was obtained from 1- a and bis(4-(propan-2-yl-d 7 )phenyl)amine. (Yield 86%, MS[M+H] + = 717)

<1-c> 화합물 1의 제조<1-c> Preparation of compound 1

Figure PCTKR2020012249-appb-I000105
Figure PCTKR2020012249-appb-I000105

3구 플라스크에 화합물 1-b를 1,2-디클로로벤젠 (0.1 M)에 녹이고 보론트리아이오다이드 (2 eq.)를 넣은 후, 아르곤 분위기 160 oC에서 4시간동안 교반하였다. 반응물을 0 ℃까지 냉각하고 N,N-디이소프로필에틸아민 (20 eq.)을 첨가한 후 1시간 교반하였다. 톨루엔과 H2O을 이용해 분액 깔대기에서 추출하였다. 추출액을 MgSO4로 건조, 농축하고 시료를 실리카 겔 컬럼 크로마토그래피로 정제한 뒤, 승화 정제하여 화합물 1을 수득하였다. (수율 15%, MS[M+H]+ = 724)Compound 1-b was dissolved in 1,2-dichlorobenzene (0.1 M) in a three necked flask and boron triiodide (2 eq.) was added, followed by stirring at 160 o C in an argon atmosphere for 4 hours. The reaction was cooled to 0° C., and N,N-diisopropylethylamine (20 eq.) was added, followed by stirring for 1 hour. Extracted from a separatory funnel using toluene and H 2 O. The extract was dried over MgSO 4 , concentrated, and the sample was purified by silica gel column chromatography, followed by sublimation purification to obtain compound 1. (Yield 15%, MS[M+H] + = 724)

합성예 2. 화합물 2의 합성Synthesis Example 2. Synthesis of Compound 2

<2-a> 화합물 2-a의 제조<2-a> Preparation of compound 2-a

Figure PCTKR2020012249-appb-I000106
Figure PCTKR2020012249-appb-I000106

합성예 <1-a>와 동일한 방법으로, 1-브로모-3-클로로-5-(메틸-d3)벤젠과 비스(4-터부틸페닐)아민으로부터 2-a를 얻었다. (수율 88%, MS[M+H]+ = 410)In the same manner as in Synthesis Example <1-a>, 2-a was obtained from 1-bromo-3-chloro-5-(methyl-d 3 )benzene and bis(4-terbutylphenyl)amine. (Yield 88%, MS[M+H] + = 410)

<2-b> 화합물 2-b의 제조<2-b> Preparation of compound 2-b

Figure PCTKR2020012249-appb-I000107
Figure PCTKR2020012249-appb-I000107

합성예 <1-a>와 동일한 방법으로, 2-a와 4-터부틸-N-(4-터부틸페닐)-2-(메틸-d3)아닐린으로부터 2-b를 얻었다. (수율 92%, MS[M+H]+ = 672)In the same manner as in Synthesis Example <1-a>, 2-b was obtained from 2-a and 4-terbutyl-N-(4-terbutylphenyl)-2-(methyl-d 3 )aniline. (Yield 92%, MS[M+H] + = 672)

<2-c> 화합물 2의 제조<2-c> Preparation of compound 2

Figure PCTKR2020012249-appb-I000108
Figure PCTKR2020012249-appb-I000108

합성예 <1-c>와 동일한 방법으로, 2-b로부터 화합물 2를 얻었다. (수율 17%, MS[M+H]+ = 679)In the same manner as in Synthesis Example <1-c>, compound 2 was obtained from 2-b. (Yield 17%, MS[M+H] + = 679)

합성예 3. 화합물 3의 합성Synthesis Example 3. Synthesis of Compound 3

<3-a> 화합물 3-a의 제조<3-a> Preparation of compound 3-a

Figure PCTKR2020012249-appb-I000109
Figure PCTKR2020012249-appb-I000109

합성예 <1-a>와 동일한 방법으로, 2-a와 5-(2-(페닐-d5)프로판-2-일-1,1,1,3,3,3-d5)-N-(4-프로판-2-일-d7)페닐)-[1,1'-바이페닐]-2',3,3',4,4',5',6,6'-d8-2-아민으로부터 3-a를 얻었다. (수율 69%, MS[M+H]+ = 804)In the same manner as in Synthesis Example <1-a>, 2-a and 5-(2-(phenyl-d 5 )propan-2-yl-1,1,1,3,3,3-d 5 )-N -(4-propan-2-yl-d 7 )phenyl)-[1,1'-biphenyl]-2',3,3',4,4',5',6,6'-d 8- Obtained 3-a from 2-amine. (Yield 69%, MS[M+H] + = 804)

<3-b> 화합물 3의 제조<3-b> Preparation of compound 3

Figure PCTKR2020012249-appb-I000110
Figure PCTKR2020012249-appb-I000110

합성예 <1-c>와 동일한 방법으로, 3-a로부터 화합물 3을 얻었다. (수율 20%, MS[M+H]+ = 812)In the same manner as in Synthesis Example <1-c>, compound 3 was obtained from 3-a. (Yield 20%, MS[M+H] + = 812)

합성예 4. 화합물 4의 합성Synthesis Example 4. Synthesis of Compound 4

<4-a> 화합물 4-a의 제조<4-a> Preparation of compound 4-a

Figure PCTKR2020012249-appb-I000111
Figure PCTKR2020012249-appb-I000111

합성예 <1-a>와 동일한 방법으로, 1-브로모-3-클로로-5-(메틸-d3)벤젠과 비스(5,5,8,8-테트라메틸-5,6,7,8-테트라하이드로나프탈렌-2-일)아민으로부터 4-a를 얻었다. (수율 86%, MS[M+H]+ = 517)In the same manner as in Synthesis Example <1-a>, 1-bromo-3-chloro-5-(methyl-d 3 )benzene and bis(5,5,8,8-tetramethyl-5,6,7, Obtained 4-a from 8-tetrahydronaphthalen-2-yl)amine. (Yield 86%, MS[M+H] + = 517)

<4-b> 화합물 4-b의 제조<4-b> Preparation of compound 4-b

Figure PCTKR2020012249-appb-I000112
Figure PCTKR2020012249-appb-I000112

합성예 <1-a>와 동일한 방법으로, 4-a와 N-(5-터부틸-2',4',6'-트리스(프로판-2-일-d7)-[1,1'-바이페닐]-2-일)-5,5,8,8-테트라메틸-5,6,7,8-테트라하이드로나프탈렌-2-아민으로부터 4-b를 얻었다. (수율 82%, MS[M+H]+ = 1039)In the same manner as in Synthesis Example <1-a>, 4-a and N-(5-terbutyl-2',4',6'-tris(propan-2-yl-d 7 )-[1,1' 4-b was obtained from -biphenyl]-2-yl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine. (Yield 82%, MS[M+H] + = 1039)

<4-c> 화합물 4 의 제조<4-c> Preparation of compound 4

Figure PCTKR2020012249-appb-I000113
Figure PCTKR2020012249-appb-I000113

합성예 <1-c>와 동일한 방법으로, 4-b로부터 화합물 4을 얻었다. (수율 12%, MS[M+H]+ = 1047)In the same manner as in Synthesis Example <1-c>, compound 4 was obtained from 4-b. (Yield 12%, MS[M+H] + = 1047)

합성예 5. 화합물 5의 합성Synthesis Example 5. Synthesis of Compound 5

<5-a> 화합물 5-a의 제조<5-a> Preparation of compound 5-a

Figure PCTKR2020012249-appb-I000114
Figure PCTKR2020012249-appb-I000114

합성예 <1-a>와 동일한 방법으로, 1-브로모-3-클로로-5-(프로판-2-일-d7)벤젠과 N-(4-터부틸페닐)-5,5,8,8-테트라메틸-5,6,7,8-테트라하이드로나프탈렌-2-아민으로부터 5-a를 얻었다. (수율 79%, MS[M+H]+ = 495)In the same manner as in Synthesis Example <1-a>, 1-bromo-3-chloro-5-(propan-2-yl-d 7 )benzene and N-(4-terbutylphenyl)-5,5,8 5-a was obtained from 8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine. (Yield 79%, MS[M+H] + = 495)

<5-b> 화합물 5-b의 제조<5-b> Preparation of compound 5-b

Figure PCTKR2020012249-appb-I000115
Figure PCTKR2020012249-appb-I000115

합성예 <1-a>와 동일한 방법으로, 5-a와 7-터부틸-N-(2,4,6-트리스(메틸-d3)디벤조[b,d]퓨란-3-아민으로부터 5-b를 얻었다. (수율 80%, MS[M+H]+ = 825)In the same manner as in Synthesis Example <1-a>, from 5-a and 7-terbutyl-N-(2,4,6-tris(methyl-d 3 )dibenzo[b,d]furan-3-amine 5-b was obtained (yield 80%, MS[M+H] + = 825)

<5-c> 화합물 5 의 제조<5-c> Preparation of compound 5

Figure PCTKR2020012249-appb-I000116
Figure PCTKR2020012249-appb-I000116

합성예 <1-c>와 동일한 방법으로, 5-b로부터 화합물 5을 얻었다. (수율 10%, MS[M+H]+ = 833)In the same manner as in Synthesis Example <1-c>, compound 5 was obtained from 5-b. (Yield 10%, MS[M+H] + = 833)

합성예 6. 화합물 6의 합성Synthesis Example 6. Synthesis of Compound 6

<6-a> 화합물 6-a의 제조<6-a> Preparation of compound 6-a

Figure PCTKR2020012249-appb-I000117
Figure PCTKR2020012249-appb-I000117

합성예 <1-a>와 동일한 방법으로, 1-브로모-3-클로로-5-(프로판-2-일-d7)벤젠과 비스(4-터부틸페닐)아민으로부터 6-a를 얻었다. (수율 88%, MS[M+H]+ = 441)In the same manner as in Synthesis Example <1-a>, 6-a was obtained from 1-bromo-3-chloro-5-(propan-2-yl-d 7 )benzene and bis(4-terbutylphenyl)amine. . (Yield 88%, MS[M+H] + = 441)

<6-b> 화합물 6-b의 제조<6-b> Preparation of compound 6-b

Figure PCTKR2020012249-appb-I000118
Figure PCTKR2020012249-appb-I000118

합성예 <1-a>와 동일한 방법으로, 6-a와 N-(4-터부틸-2-(메틸-d3)페닐)-5,6,7,8-테트라하이드로나프탈렌-5,5,6,6,7,7,8,8-d8-2-아민으로부터 6-b를 얻었다. (수율 71%, MS[M+H]+ = 709)In the same manner as in Synthesis Example <1-a>, 6-a and N-(4-terbutyl-2-(methyl-d 3 )phenyl)-5,6,7,8-tetrahydronaphthalene-5,5 ,6,6,7,7,8,8-d 8 Obtained 6-b from -2-amine. (Yield 71%, MS[M+H] + = 709)

<6-c> 화합물 6 의 제조<6-c> Preparation of compound 6

Figure PCTKR2020012249-appb-I000119
Figure PCTKR2020012249-appb-I000119

합성예 <1-c>와 동일한 방법으로, 6-b로부터 화합물 6을 얻었다. (수율 13%, MS[M+H]+ = 717)In the same manner as in Synthesis Example <1-c>, compound 6 was obtained from 6-b. (Yield 13%, MS[M+H] + = 717)

합성예 7. 화합물 7의 합성Synthesis Example 7. Synthesis of Compound 7

<7-a> 화합물 7-a의 제조<7-a> Preparation of compound 7-a

Figure PCTKR2020012249-appb-I000120
Figure PCTKR2020012249-appb-I000120

합성예 <1-a>와 동일한 방법으로, 1-브로모-3,5-디클로로벤젠과 비스(4-터부틸페닐)아민으로부터 7-a를 얻었다. (수율 92%, MS[M+H]+ = 426)In the same manner as in Synthesis Example <1-a>, 7-a was obtained from 1-bromo-3,5-dichlorobenzene and bis(4-terbutylphenyl)amine. (Yield 92%, MS[M+H] + = 426)

<7-b> 화합물 7-b의 제조<7-b> Preparation of compound 7-b

Figure PCTKR2020012249-appb-I000121
Figure PCTKR2020012249-appb-I000121

합성예 <1-a>와 동일한 방법으로, 7-a와 비스(5,5,8,8-테트라메틸-5,6,7,8-테트라하이드로나프탈렌-2-일)아민으로부터 7-b를 얻었다. (수율 87%, MS[M+H]+ = 779)In the same manner as in Synthesis Example <1-a>, 7-b from 7-a and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine Got it. (Yield 87%, MS[M+H] + = 779)

<7-c> 화합물 7-c의 제조<7-c> Preparation of compound 7-c

Figure PCTKR2020012249-appb-I000122
Figure PCTKR2020012249-appb-I000122

3구 플라스크에 화합물 7-b를 1,2-디클로로벤젠 (0.1 M)에 녹이고 보론트리아이오다이드 (2 eq.)를 넣은 후, 아르곤 분위기 160 oC에서 8시간동안 교반하였다. 반응물을 0 ℃까지 냉각하고 N,N-디이소프로필에틸아민 (20 eq.)을 첨가한 후 1시간 교반하였다. 톨루엔과 H2O을 이용해 분액 깔대기에서 추출하였다. 추출액을 MgSO4로 건조, 농축하고 시료를 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 7-c를 수득하였다. (수율 23%, MS[M+H]+ = 787)Compound 7-b was dissolved in 1,2-dichlorobenzene (0.1 M) in a three necked flask and boron triiodide (2 eq.) was added, followed by stirring at 160 o C in an argon atmosphere for 8 hours. The reaction was cooled to 0° C., and N,N-diisopropylethylamine (20 eq.) was added, followed by stirring for 1 hour. Extracted from a separatory funnel using toluene and H 2 O. The extract was dried over MgSO 4 , concentrated, and the sample was purified by silica gel column chromatography to obtain compound 7-c. (Yield 23%, MS[M+H] + = 787)

<7-d> 화합물 7의 제조<7-d> Preparation of compound 7

Figure PCTKR2020012249-appb-I000123
Figure PCTKR2020012249-appb-I000123

3구 플라스크에 화합물 7-c (1 eq.)와 4a,9a-비스(메틸-d3)-2,3,4,4a,9,9a-헥사하이드로-1H-카바졸 (1.1 eq.)을 톨루엔 (0.3 M)에 녹이고 소듐 터부톡사이드 (1.5 eq.), 비스(트리-터부틸포스핀)팔라듐(0) (0.01 eq.)을 넣은 후, 아르곤 분위기 환류 조건하에서 4시간 동안 교반하였다. 반응이 종료되면 상온으로 냉각한 후, H2O를 넣고 반응액을 분액 깔대기에 옮겨 추출하였다. 추출액을 MgSO4로 건조, 농축하고 시료를 실리카 겔 컬럼 크로마토그래피로 정제하고 승화 정제하여 화합물 7을 수득하였다. (수율 63%, MS[M+H]+ = 958)In a three necked flask, compound 7-c (1 eq.) and 4a ,9a-bis(methyl-d 3 )-2,3,4,4a,9,9a-hexahydro-1H-carbazole (1.1 eq.) Was dissolved in toluene (0.3 M), sodium terbutoxide (1.5 eq.) and bis(tri-terbutylphosphine) palladium (0) (0.01 eq.) were added, followed by stirring under reflux conditions in an argon atmosphere for 4 hours. . When the reaction was completed, after cooling to room temperature, H 2 O was added and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO 4 , concentrated, and the sample was purified by silica gel column chromatography, followed by sublimation purification to obtain compound 7. (Yield 63%, MS[M+H] + = 958)

합성예 8. 화합물 8의 합성Synthesis Example 8. Synthesis of Compound 8

<8-a> 화합물 8-a의 제조<8-a> Preparation of compound 8-a

Figure PCTKR2020012249-appb-I000124
Figure PCTKR2020012249-appb-I000124

합성예 <1-a>와 동일한 방법으로, 1-브로모-3-클로로-5-(프로판-2-일-d7)벤젠과 N-(4-터부틸페닐)-5,5,8,8-테트라메틸-3-페닐-5,6,7,8-테트라하이드로나프탈렌-2-아민으로부터 8-a를 얻었다. (수율 88%, MS[M+H]+ = 571)In the same manner as in Synthesis Example <1-a>, 1-bromo-3-chloro-5-(propan-2-yl-d 7 )benzene and N-(4-terbutylphenyl)-5,5,8 8-a was obtained from 8-tetramethyl-3-phenyl-5,6,7,8-tetrahydronaphthalen-2-amine. (Yield 88%, MS[M+H] + = 571)

<8-b> 화합물 8-b의 제조<8-b> Preparation of compound 8-b

Figure PCTKR2020012249-appb-I000125
Figure PCTKR2020012249-appb-I000125

합성예 <1-a>와 동일한 방법으로, 8-a와 N-(4-터부틸페닐)-2-(메틸-d3)-4-(터부틸-d9)아닐린으로부터 8-b를 얻었다. (수율 76%, MS[M+H]+ = 842)The manner similar to that of Example <1-a>, the 8-a with N- (4- emitter-butylphenyl) -2- (2 -d 3) 8-b from 4- (emitter-butyl -d 9) aniline Got it. (Yield 76%, MS[M+H] + = 842)

<8-c> 화합물 8의 제조<8-c> Preparation of compound 8

Figure PCTKR2020012249-appb-I000126
Figure PCTKR2020012249-appb-I000126

합성예 <1-c>와 동일한 방법으로, 8-b로부터 화합물 8을 얻었다. (수율 10%, MS[M+H]+ = 850)In the same manner as in Synthesis Example <1-c>, compound 8 was obtained from 8-b. (Yield 10%, MS[M+H] + = 850)

합성예 9. 화합물 9의 합성Synthesis Example 9. Synthesis of Compound 9

<9-a> 화합물 9-a의 제조<9-a> Preparation of compound 9-a

Figure PCTKR2020012249-appb-I000127
Figure PCTKR2020012249-appb-I000127

합성예 <1-a>와 동일한 방법으로, 1-브로모-3,5-디클로로벤젠과 비스(5,5,8,8-테트라메틸-5,6,7,8-테트라하이드로나프탈렌-2-일)아민으로부터 화합물 9-a를 얻었다. (수율 86%, MS[M+H]+ = 534)In the same manner as in Synthesis Example <1-a>, 1-bromo-3,5-dichlorobenzene and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2 Compound 9-a was obtained from -yl)amine. (Yield 86%, MS[M+H] + = 534)

<9-b> 화합물 9-b의 제조<9-b> Preparation of compound 9-b

Figure PCTKR2020012249-appb-I000128
Figure PCTKR2020012249-appb-I000128

합성예 <1-a>와 동일한 방법으로, 9-a와 4-터부틸-N-(3-(4a,9a-디메틸-1,2,3,4,4a,9a-헥사하이드로-9H-카바졸-9-일)페닐)-2-(메틸-d3)아닐린으로부터 화합물 9-b를 얻었다. (수율 66%, MS[M+H]+ = 939)In the same manner as in Synthesis Example <1-a>, 9-a and 4-terbutyl-N-(3-(4a,9a-dimethyl-1,2,3,4,4a,9a-hexahydro-9H- Compound 9-b was obtained from carbazol-9-yl)phenyl)-2-(methyl-d 3 )aniline. (Yield 66%, MS[M+H] + = 939)

<9-c> 화합물 9-c의 제조<9-c> Preparation of compound 9-c

Figure PCTKR2020012249-appb-I000129
Figure PCTKR2020012249-appb-I000129

합성예 <7-c>와 동일한 방법으로, 화합물 9-b로부터 화합물 9-c를 얻었다. (수율 31%, MS[M+H]+ = 947)In the same manner as in Synthesis Example <7-c>, compound 9-c was obtained from compound 9-b. (Yield 31%, MS[M+H] + = 947)

<9-d> 화합물 9의 제조<9-d> Preparation of compound 9

Figure PCTKR2020012249-appb-I000130
Figure PCTKR2020012249-appb-I000130

합성예 <7-d>와 동일한 방법으로, 화합물 9-c로부터 화합물 9를 얻었다. (수율 72%, MS[M+H]+ = 1118)In the same manner as in Synthesis Example <7-d>, compound 9 was obtained from compound 9-c. (Yield 72%, MS[M+H] + = 1118)

합성예 10. 화합물 10의 합성Synthesis Example 10. Synthesis of Compound 10

<10-a> 화합물 10-a의 제조<10-a> Preparation of compound 10-a

Figure PCTKR2020012249-appb-I000131
Figure PCTKR2020012249-appb-I000131

합성예 <1-a>와 동일한 방법으로, 1-브로모-3-클로로-5-(에틸-d5)벤젠과 4-터부틸-2-(메틸-d3)-N-(3-터펜틸페닐)아닐린으로부터 10-a를 얻었다. (수율 95%, MS[M+H]+ = 456)In the same manner as in Synthesis Example <1-a>, 1-bromo-3-chloro-5-(ethyl-d 5 )benzene and 4-terbutyl-2-(methyl-d 3 )-N-(3- 10-a was obtained from terpentylphenyl)aniline. (Yield 95%, MS[M+H] + = 456)

<10-b> 화합물 10-b의 제조<10-b> Preparation of compound 10-b

Figure PCTKR2020012249-appb-I000132
Figure PCTKR2020012249-appb-I000132

합성예 <1-a>와 동일한 방법으로, 10-a와 N-(4-(터부틸)페닐)다이벤조 [b,d]티오펜-2-아민으로부터 10-b를 얻었다. (수율 76%, MS[M+H]+ = 751)In the same manner as in Synthesis Example <1-a>, 10-b was obtained from 10-a and N-(4-(terbutyl)phenyl)dibenzo[b,d]thiophen-2-amine. (Yield 76%, MS[M+H] + = 751)

<10-c> 화합물 10의 제조<10-c> Preparation of compound 10

Figure PCTKR2020012249-appb-I000133
Figure PCTKR2020012249-appb-I000133

합성예 <1-c>와 동일한 방법으로, 10-b로부터 화합물 10을 얻었다. (수율 12%, MS[M+H]+ = 759)In the same manner as in Synthesis Example <1-c>, compound 10 was obtained from 10-b. (Yield 12%, MS[M+H] + = 759)

합성예 11. 화합물 11의 합성Synthesis Example 11. Synthesis of Compound 11

<11-a> 화합물 11-a의 제조<11-a> Preparation of compound 11-a

Figure PCTKR2020012249-appb-I000134
Figure PCTKR2020012249-appb-I000134

합성예 <1-a>와 동일한 방법으로, 1-브로모-3-클로로-5-(프로판-2-일-d7)벤젠과 비스(4-터부틸페닐)아민으로부터 11-a를 얻었다. (수율 91%, MS[M+H]+ = 441)In the same manner as in Synthesis Example <1-a>, 11-a was obtained from 1-bromo-3-chloro-5-(propan-2-yl-d 7 )benzene and bis(4-terbutylphenyl)amine. . (Yield 91%, MS[M+H] + = 441)

<11-b> 화합물 11-b의 제조<11-b> Preparation of compound 11-b

Figure PCTKR2020012249-appb-I000135
Figure PCTKR2020012249-appb-I000135

합성예 <1-a>와 동일한 방법으로, 11-a와 N1,N1-비스(2-플루오로페닐)-N3-(2,4,6-트리(메틸-d- 3)페닐)벤젠-1,3-디아민으로부터 11-b를 얻었다. (수율 63%, MS[M+H]+ = 828)In the same manner as in Synthesis Example <1-a>, 11-a and N 1 ,N 1 -bis(2-fluorophenyl)-N 3 -(2,4,6-tri(methyl-d - 3 )phenyl ) 11-b was obtained from benzene-1,3-diamine. (Yield 63%, MS[M+H] + = 828)

<11-c> 화합물 11의 제조<11-c> Preparation of compound 11

Figure PCTKR2020012249-appb-I000136
Figure PCTKR2020012249-appb-I000136

합성예 <1-c>와 동일한 방법으로, 11-b로부터 화합물 11을 얻었다. (수율 8%, MS[M+H]+ = 836)In the same manner as in Synthesis Example <1-c>, compound 11 was obtained from 11-b. (Yield 8%, MS[M+H] + = 836)

합성예 12. 화합물 12의 합성Synthesis Example 12. Synthesis of Compound 12

<12-a> 화합물 12-a의 제조<12-a> Preparation of compound 12-a

Figure PCTKR2020012249-appb-I000137
Figure PCTKR2020012249-appb-I000137

합성예 <1-a>와 동일한 방법으로, 1-브로모-3-클로로-5-(에틸-d5)벤젠과 N-(4-터부틸페닐)디벤조[b,d]퓨란-2-아민으로부터 12-a를 얻었다. (수율 88%, MS[M+H]+ = 459)In the same manner as in Synthesis Example <1-a>, 1-bromo-3-chloro-5-(ethyl-d 5 )benzene and N-(4-terbutylphenyl)dibenzo[b,d]furan-2 -Obtained 12-a from amine. (Yield 88%, MS[M+H] + = 459)

<12-b> 화합물 12-b의 제조<12-b> Preparation of compound 12-b

Figure PCTKR2020012249-appb-I000138
Figure PCTKR2020012249-appb-I000138

합성예 <1-a>와 동일한 방법으로, 12-a와 5,5,8,8-테트라메틸-N-(2,4,5-트리스(메틸-d3)페닐)-5,6,7,8-테트라하이드로나프탈렌-2-아민으로부터 12-b를 얻었다. (수율 82%, MS[M+H]+ =753)In the same manner as in Synthesis Example <1-a>, 12-a and 5,5,8,8-tetramethyl-N-(2,4,5-tris(methyl-d 3 )phenyl)-5,6, 12-b was obtained from 7,8-tetrahydronaphthalen-2-amine. (Yield 82%, MS[M+H] + =753)

<12-c> 화합물 12의 제조<12-c> Preparation of compound 12

Figure PCTKR2020012249-appb-I000139
Figure PCTKR2020012249-appb-I000139

합성예 <1-c>와 동일한 방법으로, 12-b로부터 화합물 12을 얻었다. (수율 11%, MS[M+H]+ = 761)In the same manner as in Synthesis Example <1-c>, compound 12 was obtained from 12-b. (Yield 11%, MS[M+H] + = 761)

합성예 13. 화합물 13의 합성Synthesis Example 13. Synthesis of Compound 13

<13-a> 화합물 13-a의 제조<13-a> Preparation of compound 13-a

Figure PCTKR2020012249-appb-I000140
Figure PCTKR2020012249-appb-I000140

합성예 <1-a>와 동일한 방법으로, 화합물 2-a와 N-(4-터부틸페닐)-2,8-비스(메틸-d3)디벤조[b,d]퓨란-4-아민으로부터 13-a를 얻었다. (수율 81%, MS[M+H]+ = 722)In the same manner as in Synthesis Example <1-a>, compound 2-a and N-(4-terbutylphenyl)-2,8-bis(methyl-d 3 )dibenzo[b,d]furan-4-amine 13-a was obtained from (Yield 81%, MS[M+H] + = 722)

<13-b> 화합물 13의 제조<13-b> Preparation of compound 13

Figure PCTKR2020012249-appb-I000141
Figure PCTKR2020012249-appb-I000141

합성예 <1-c>와 동일한 방법으로, 13-a로부터 화합물 13을 얻었다. (수율 16%, MS[M+H]+ = 730)In the same manner as in Synthesis Example <1-c>, compound 13 was obtained from 13-a. (Yield 16%, MS[M+H] + = 730)

합성예 14. 화합물 14의 합성Synthesis Example 14. Synthesis of Compound 14

<14-a> 화합물 14-a의 제조<14-a> Preparation of compound 14-a

Figure PCTKR2020012249-appb-I000142
Figure PCTKR2020012249-appb-I000142

합성예 <1-a>와 동일한 방법으로, 화합물 1-a와 2,4,6-트리스(메틸-d3)-N-(4-(트리메틸실릴)페닐)아닐린으로부터 14-a를 얻었다. (수율 89%, MS[M+H]+ = 741)In the same manner as in Synthesis Example <1-a>, 14-a was obtained from compound 1-a and 2,4,6-tris(methyl-d 3 )-N-(4-(trimethylsilyl)phenyl)aniline. (Yield 89%, MS[M+H] + = 741)

<14-b> 화합물 14의 제조<14-b> Preparation of compound 14

Figure PCTKR2020012249-appb-I000143
Figure PCTKR2020012249-appb-I000143

합성예 <1-c>와 동일한 방법으로, 14-a로부터 화합물 14를 얻었다. (수율 14%, MS[M+H]+ = 749)Compound 14 was obtained from 14-a in the same manner as in Synthesis Example <1-c>. (Yield 14%, MS[M+H] + = 749)

합성예 15. 화합물 15의 합성Synthesis Example 15. Synthesis of Compound 15

<15-a> 화합물 15-a의 제조<15-a> Preparation of compound 15-a

Figure PCTKR2020012249-appb-I000144
Figure PCTKR2020012249-appb-I000144

합성예 <1-a>와 동일한 방법으로, 1-브로모-3-클로로-5-(에틸-d5)벤젠과 비스(5,5,8,8-테트라메틸-5,6,7,8-테트라하이드로나프탈렌-2-일)아민으로부터 15-a를 얻었다. (수율 81%, MS[M+H]+ = 533)In the same manner as in Synthesis Example <1-a>, 1-bromo-3-chloro-5-(ethyl-d 5 )benzene and bis(5,5,8,8-tetramethyl-5,6,7, 15-a was obtained from 8-tetrahydronaphthalen-2-yl)amine. (Yield 81%, MS[M+H] + = 533)

<15-b> 화합물 15-b의 제조<15-b> Preparation of compound 15-b

Figure PCTKR2020012249-appb-I000145
Figure PCTKR2020012249-appb-I000145

합성예 <1-a>와 동일한 방법으로, 15-a와 N-(4-터부틸페닐)-2,9,9-트리스(메틸-d3)-9H-플루오렌-1,4,5,6,7,8-d6-3-아민으로부터 15-b를 얻었다. (수율 71%, MS[M+H]+ =867)In the same manner as in Synthesis Example <1-a>, 15-a and N-(4-terbutylphenyl)-2,9,9-tris(methyl-d 3 )-9H-fluorene-1,4,5 , 6,7,8-d 6 was obtained from 15-b-3-amine. (Yield 71%, MS[M+H] + =867)

<15-c> 화합물 15의 제조<15-c> Preparation of compound 15

Figure PCTKR2020012249-appb-I000146
Figure PCTKR2020012249-appb-I000146

합성예 <1-c>와 동일한 방법으로, 15-b로부터 화합물 15를 얻었다. (수율 12%, MS[M+H]+ = 875)In the same manner as in Synthesis Example <1-c>, compound 15 was obtained from 15-b. (Yield 12%, MS[M+H] + = 875)

합성예 16. 화합물 16의 합성Synthesis Example 16. Synthesis of Compound 16

<16-a> 화합물 16-a의 제조<16-a> Preparation of compound 16-a

Figure PCTKR2020012249-appb-I000147
Figure PCTKR2020012249-appb-I000147

합성예 <1-a>와 동일한 방법으로, 1-브로모-3-클로로-5-(프로판-2-일-d7)벤젠과 N-(5,5,8,8-테트라메틸-3-(메틸-d3)-5,6,7,8-테트라하이드로나프탈렌-2-일)-9,10-디하이드로-9,10-에타노안트라센-2-아민으로부터 16-a를 얻었다. (수율 85%, MS[M+H]+ = 584)In the same manner as in Synthesis Example <1-a>, 1-bromo-3-chloro-5-(propan-2-yl-d 7 )benzene and N-(5,5,8,8-tetramethyl-3 16-a was obtained from -(methyl-d3)-5,6,7,8-tetrahydronaphthalen-2-yl)-9,10-dihydro-9,10-ethanoanthracene-2-amine. (Yield 85%, MS[M+H] + = 584)

<16-b> 화합물 16-b의 제조<16-b> Preparation of compound 16-b

Figure PCTKR2020012249-appb-I000148
Figure PCTKR2020012249-appb-I000148

합성예 <1-a>와 동일한 방법으로, 16-a와 N-(4-터부틸페닐)-2-(에틸-d5)-4-(메틸-d3)벤젠-3,5,6-d3-아민으로부터 16-b를 얻었다. (수율 82%, MS[M+H]+ = 826)In the same manner as in Synthesis Example <1-a>, 16-a and N-(4- terbutylphenyl)-2-(ethyl-d 5 )-4-(methyl-d 3 )benzene-3,5,6 16-b was obtained from -d 3 -amine. (Yield 82%, MS[M+H] + = 826)

<16-c> 화합물 16의 제조<16-c> Preparation of compound 16

Figure PCTKR2020012249-appb-I000149
Figure PCTKR2020012249-appb-I000149

합성예 <1-c>와 동일한 방법으로, 16-b로부터 화합물 16를 얻었다. (수율 11%, MS[M+H]+ = 834)Compound 16 was obtained from 16-b in the same manner as in Synthesis Example <1-c>. (Yield 11%, MS[M+H] + = 834)

합성예 17. 화합물 17의 합성Synthesis Example 17. Synthesis of Compound 17

<17-a> 화합물 17-a의 제조<17-a> Preparation of compound 17-a

Figure PCTKR2020012249-appb-I000150
Figure PCTKR2020012249-appb-I000150

합성예 <1-a>와 동일한 방법으로, 2-a와 6-터부틸-4a,9a-비스(메틸-d3)-2,3,4,4a,9,9a-헥사하이드로-1H-카바졸로부터 17-a를 얻었다. (수율 88%, MS[M+H]+ = 636)In the same manner as in Synthesis Example <1-a>, 2-a and 6- terbutyl-4a,9a-bis(methyl-d 3 )-2,3,4,4a,9,9a-hexahydro-1H- 17-a was obtained from carbazole. (Yield 88%, MS[M+H] + = 636)

<17-b> 화합물 17의 제조<17-b> Preparation of compound 17

Figure PCTKR2020012249-appb-I000151
Figure PCTKR2020012249-appb-I000151

합성예 <1-c>와 동일한 방법으로, 17-a로부터 화합물 17를 얻었다. (수율 17%, MS[M+H]+ = 644)In the same manner as in Synthesis Example <1-c>, compound 17 was obtained from 17-a. (Yield 17%, MS[M+H] + = 644)

합성예 18. 화합물 18의 합성Synthesis Example 18. Synthesis of Compound 18

<18-a> 화합물 18-a의 제조<18-a> Preparation of compound 18-a

Figure PCTKR2020012249-appb-I000152
Figure PCTKR2020012249-appb-I000152

합성예 <1-a>와 동일한 방법으로, 1-브로모-3,5-디클로로벤젠과 비스(4-(메틸-d3)페닐)아민으로부터 18-a를 얻었다. (수율 83%, MS[M+H]+ = 348)In the same manner as in Synthesis Example <1-a>, 18-a was obtained from 1-bromo-3,5-dichlorobenzene and bis(4-(methyl-d 3 )phenyl)amine. (Yield 83%, MS[M+H] + = 348)

<18-b> 화합물 18-b의 제조<18-b> Preparation of compound 18-b

Figure PCTKR2020012249-appb-I000153
Figure PCTKR2020012249-appb-I000153

합성예 <1-a>와 동일한 방법으로, 18-a와 N-(4-(메틸-d3)페닐)-3-(트리플루오로메톡시)아닐린으로부터 화합물 18-b를 얻었다. (수율 81%, MS[M+H]+ = 582)In the same manner as in Synthesis Example <1-a>, compound 18-b was obtained from 18-a and N-(4-(methyl-d 3 )phenyl)-3-(trifluoromethoxy)aniline. (Yield 81%, MS[M+H] + = 582)

<18-c> 화합물 18-c의 제조<18-c> Preparation of compound 18-c

Figure PCTKR2020012249-appb-I000154
Figure PCTKR2020012249-appb-I000154

합성예 <7-c>와 동일한 방법으로, 화합물 18-b로부터 화합물 18-c를 얻었다. (수율 24%, MS[M+H]+ = 590)In the same manner as in Synthesis Example <7-c>, compound 18-c was obtained from compound 18-b. (Yield 24%, MS[M+H] + = 590)

<18-d> 화합물 18의 제조<18-d> Preparation of compound 18

Figure PCTKR2020012249-appb-I000155
Figure PCTKR2020012249-appb-I000155

합성예 <7-d>와 동일한 방법으로, 화합물 18-c와 비스(4-터부틸페닐)아민으로부터 화합물 18를 얻었다. (수율 59%, MS[M+H]+ = 835)In the same manner as in Synthesis Example <7-d>, compound 18 was obtained from compound 18-c and bis(4-terbutylphenyl)amine. (Yield 59%, MS[M+H] + = 835)

합성예 19. 화합물 19의 합성Synthesis Example 19. Synthesis of Compound 19

<19-a> 화합물 19-a의 제조<19-a> Preparation of compound 19-a

Figure PCTKR2020012249-appb-I000156
Figure PCTKR2020012249-appb-I000156

합성예 <1-a>와 동일한 방법으로, 7-a와 N-(4-터부틸페닐)디벤조[b,d]퓨란-3-아민으로부터 19-a를 얻었다. (수율 89%, MS[M+H]+ = 705)In the same manner as in Synthesis Example <1-a>, 19-a was obtained from 7-a and N-(4-terbutylphenyl)dibenzo[b,d]furan-3-amine. (Yield 89%, MS[M+H] + = 705)

<19-b> 화합물 19-b의 제조<19-b> Preparation of compound 19-b

Figure PCTKR2020012249-appb-I000157
Figure PCTKR2020012249-appb-I000157

합성예 <7-c>와 동일한 방법으로, 19-a로부터 19-b를 얻었다. (수율 17%, MS[M+H]+ = 713)In the same manner as in Synthesis Example <7-c>, 19-b was obtained from 19-a. (Yield 17%, MS[M+H] + = 713)

<19-c> 화합물 19의 제조<19-c> Preparation of compound 19

Figure PCTKR2020012249-appb-I000158
Figure PCTKR2020012249-appb-I000158

합성예 <7-d>와 동일한 방법으로, 19-b와 2,3,6,7-테트라키스(메틸-d3)-9H-카바졸로부터 화합물 19를 얻었다. (수율 63%, MS[M+H]+ = 912)In the same manner as in Synthesis Example <7-d>, compound 19 was obtained from 19-b and 2,3,6,7-tetrakis(methyl-d 3 )-9H-carbazole. (Yield 63%, MS[M+H] + = 912)

합성예 20. 화합물 20의 합성Synthesis Example 20. Synthesis of Compound 20

<20-a> 화합물 20-a의 제조<20-a> Preparation of compound 20-a

Figure PCTKR2020012249-appb-I000159
Figure PCTKR2020012249-appb-I000159

3구 플라스크에 1-브로모-3-클로로-5-(메틸-d5)벤젠 (1 eq.)과 4-터부틸아닐린 (2.1 eq.)을 톨루엔 (0.3 M)에 녹이고 소듐 터부톡사이드 (3 eq.), 비스(트리-터부틸포스핀)팔라듐(0) (0.01 eq.)을 넣은 후, 아르곤 분위기 환류 조건하에서 2시간동안 교반하였다. 반응이 종료되면 상온으로 냉각한 후, H2O를 넣고 반응액을 분액 깔대기에 옮겨 추출하였다. 추출액을 MgSO4로 건조, 농축하고 시료를 실리카 겔 컬럼 크로마토그래피로 정제하여 화합물 20-a 를 수득하였다. (수율 85%, MS[M+H]+ = 390)In a 3-neck flask, 1-bromo-3-chloro-5-(methyl-d 5 )benzene (1 eq.) and 4-terbutylaniline (2.1 eq.) were dissolved in toluene (0.3 M) and sodium terbutoxide (3 eq.) and bis (tri-terbutylphosphine) palladium (0) (0.01 eq.) were added, followed by stirring for 2 hours under reflux conditions in an argon atmosphere. When the reaction was completed, after cooling to room temperature, H 2 O was added and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO 4 , concentrated, and the sample was purified by silica gel column chromatography to obtain compound 20-a. (Yield 85%, MS[M+H] + = 390)

<20-b> 화합물 20-b의 제조<20-b> Preparation of compound 20-b

Figure PCTKR2020012249-appb-I000160
Figure PCTKR2020012249-appb-I000160

합성예 <1-a>와 동일한 방법으로, 20-a와 2,2'-(프로판-2,2-다이일-1,1,1,3,3,3-d6)비스(4-브로모-1-(메틸-d3)벤젠)으로부터 20-b를 얻었다. (수율 71%, MS[M+H]+ = 622)In the same manner as in Synthesis Example <1-a>, 20-a and 2,2'-(propane-2,2-diyl-1,1,1,3,3,3-d 6 )bis(4- 20-b was obtained from bromo-1-(methyl-d 3 )benzene). (Yield 71%, MS[M+H] + = 622)

<20-c> 화합물 20의 제조<20-c> Preparation of compound 20

Figure PCTKR2020012249-appb-I000161
Figure PCTKR2020012249-appb-I000161

합성예 <1-c>와 동일한 방법으로, 20-b로부터 화합물 20을 얻었다. (수율 5%, MS[M+H]+ = 630)In the same manner as in Synthesis Example <1-c>, compound 20 was obtained from 20-b. (Yield 5%, MS[M+H] + = 630)

<실험예 1: 소자예><Experimental Example 1: Device Example>

실시예 1.Example 1.

ITO(indium tin oxide)가 1,400Å의 두께로 박막 코팅된 유리 기판을 세제를 녹인 증류수에 넣고 초음파로 세척 하였다. 이 때, 세제로는 피셔사(Fischer Co.) 제품을 사용하였으며, 증류수로는 밀리포어사(Millipore Co.) 제품의 필터(Filter)로 2차로 걸러진 증류수를 사용하였다. ITO를 30분간 세척한 후, 증류수로 2회 반복하여 초음파 세척을 10분간 진행하였다. 증류수 세척이 끝난 후, 이소프로필알콜, 아세톤, 메탄올의 용제로 초음파 세척을 하고 건조시킨 후, 플라즈마 세정기로 수송시켰다. 또한, 산소 플라즈마를 이용하여 상기 기판을 5분간 세정한 후 진공 증착기로 기판을 수송시켰다.A glass substrate coated with a thin film of 1,400Å of ITO (indium tin oxide) was placed in distilled water dissolved in a detergent and washed with ultrasonic waves. At this time, Fischer Co. product was used as a detergent, and distilled water secondarily filtered with a filter made by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

상기와 같이 준비된 ITO 투명 전극 위에 하기 HI-A와 HI-B을 각각 650 Å, 50 Å의 두께로 열 진공증착하여 제1 정공주입층 및 제2 정공주입층을 형성하였다. On the ITO transparent electrode prepared as described above, the following HI-A and HI-B were thermally vacuum deposited to a thickness of 650 Å and 50 Å, respectively, to form a first hole injection layer and a second hole injection layer.

상기 정공 주입층 위에 하기 HT-A를 600 Å의 두께로 진공 증착하여 정공수송층을 형성하였다.On the hole injection layer, the following HT-A was vacuum deposited to a thickness of 600 Å to form a hole transport layer.

상기 정공수송층 위에 하기 HT-B를 50 Å의 두께로 진공 증착하여 전자차단층을 형성하였다. On the hole transport layer, the following HT-B was vacuum deposited to a thickness of 50 Å to form an electron blocking layer.

이어서, 상기 전자차단층 위에 청색 발광 도펀트로 하기 화합물 1을 발광층 총 중량 대비 4wt%, 호스트로 하기 BH-1를 발광층 총 중량 대비 96wt%, 200Å의 두께로 진공 증착하여 발광층을 형성하였다. Subsequently, a light emitting layer was formed by vacuum deposition of Compound 1 as a blue light-emitting dopant on the electron blocking layer to a thickness of 4 wt% based on the total weight of the light-emitting layer and BH-1 as a host to a thickness of 96 wt% and 200 Å based on the total weight of the light-emitting layer.

그 다음에 상기 발광층 위에 제1 전자수송층으로 하기 화합물 ET-A 50Å을 진공 증착하고, 연이어 하기 ET-B 및 LiQ 를 1:1 중량비로 진공증착하여 360Å의 두께로 제2 전자수송층을 형성하였다. Then, 50 Å of the following compound ET-A was vacuum-deposited on the light-emitting layer as a first electron transport layer, and subsequently ET-B and LiQ were vacuum-deposited at a 1:1 weight ratio to form a second electron transport layer having a thickness of 360 Å.

상기 제2 전자수송층 위에 LiQ를 진공 증착하여 5Å의 두께로 진공증착하여 전자주입층을 형성하였다. LiQ was vacuum-deposited on the second electron transport layer and vacuum-deposited to a thickness of 5 Å to form an electron injection layer.

상기 전자주입층 위에 220Å 두께로 알루미늄과 은을 10:1의 중량비로 증착하고 그 위에 알루미늄을 1000Å 두께로 증착하여 음극을 형성하였다.On the electron injection layer, aluminum and silver were deposited at a thickness of 220 Å at a weight ratio of 10:1, and aluminum was deposited at a thickness of 1000 Å on the electron injection layer to form a cathode.

상기의 과정에서 유기물의 증착속도는 0.4 ~ 0.9 Å/sec를 유지하였고, 음극의 알루미늄은 2 Å/sec의 증착 속도를 유지하였으며, 증착시 진공도는 1 × 10-7 ~ 5 × 10-8 torr를 유지하여, 유기 발광 소자를 제작하였다.In the above process, the deposition rate of organic materials was maintained at 0.4 ~ 0.9 Å/sec, and the deposition rate of aluminum at the cathode was maintained at 2 Å/sec, and the vacuum degree during deposition was 1 × 10 -7 ~ 5 × 10 -8 torr. By maintaining the, an organic light emitting device was manufactured.

Figure PCTKR2020012249-appb-I000162
Figure PCTKR2020012249-appb-I000162

실시예 2 내지 20 및 비교예 1 내지 4Examples 2 to 20 and Comparative Examples 1 to 4

상기 실시예 1에서 발광층의 도펀트와 호스트로 상기 화합물 1과 BH-1 대신 하기 표 1에 기재된 화합물을 사용한 것을 제외하고는 실시예 1과 동일한 방법을 이용하여 실시예 2 내지 20 및 비교예 1 내지 4의 유기 발광 소자를 각각 제작하였다.In Example 1, Examples 2 to 20 and Comparative Examples 1 to 1 were used in the same manner as in Example 1, except that the compounds shown in Table 1 were used instead of Compounds 1 and BH-1 as the dopant and host of the emission layer. Each of the organic light emitting devices of 4 was manufactured.

Figure PCTKR2020012249-appb-I000163
Figure PCTKR2020012249-appb-I000163

Figure PCTKR2020012249-appb-I000164
Figure PCTKR2020012249-appb-I000164

상기 실시예 1 내지 20 및 비교예 1 내지 4의 유기 발광 소자에 10 mA/cm2의 전류 밀도를 인가할 때의 전압, 효율(cd/A/y) 및 20 mA/cm2의 전류 밀도를 인가할 때의 수명(T95)을 측정하고, 그 결과를 하기 표 1에 나타내었다. 이 때, T95는 전류 밀도 20 mA/cm2에서의 초기 휘도를 100%로 하였을 때 휘도가 95%로 감소되는데 소요되는 시간을 비교예 1을 기준으로 비율을 나타내었다.Voltage, efficiency (cd/A/y) and current density of 20 mA/cm 2 when applying a current density of 10 mA/cm 2 to the organic light emitting devices of Examples 1 to 20 and Comparative Examples 1 to 4 The lifespan (T 95 ) at the time of application was measured, and the results are shown in Table 1 below. At this time, T 95 represents the ratio of the time required for the luminance to decrease to 95% when the initial luminance at a current density of 20 mA/cm 2 is 100%, based on Comparative Example 1.

EntryEntry 도펀트Dopant 호스트Host 10 mA/cm2 10 mA / cm 2 20 mA/cm2 20 mA / cm 2 구동 전압 (V)Driving voltage (V) 환산 효율 (cd/A/y)Conversion efficiency (cd/A/y) T95 (%)T 95 (%) 실시예 1Example 1 화합물 1Compound 1 BH-1 BH-1 3.89 3.89 43.1 43.1 217217 실시예 2Example 2 화합물 2Compound 2 BH-1 BH-1 3.84 3.84 43.7 43.7 207207 실시예 3Example 3 화합물 3Compound 3 BH-1 BH-1 3.88 3.88 42.2 42.2 233233 실시예 4Example 4 화합물 4Compound 4 BH-1 BH-1 3.80 3.80 45.4 45.4 295295 실시예 5Example 5 화합물 5Compound 5 BH-1 BH-1 3.88 3.88 45.0 45.0 271271 실시예 6Example 6 화합물 6Compound 6 BH-1 BH-1 3.84 3.84 44.5 44.5 238238 실시예 7Example 7 화합물 7Compound 7 BH-1 BH-1 3.81 3.81 44.2 44.2 279279 실시예 8Example 8 화합물 8Compound 8 BH-1 BH-1 3.82 3.82 43.6 43.6 293293 실시예 9Example 9 화합물 9Compound 9 BH-1 BH-1 3.87 3.87 44.4 44.4 243243 실시예 10Example 10 화합물 10Compound 10 BH-2 BH-2 3.72 3.72 44.3 44.3 238238 실시예 11Example 11 화합물 11Compound 11 BH-2 BH-2 3.79 3.79 45.7 45.7 253253 실시예 12Example 12 화합물 12Compound 12 BH-2 BH-2 3.71 3.71 44.9 44.9 225225 실시예 13Example 13 화합물 13Compound 13 BH-2 BH-2 3.73 3.73 42.6 42.6 203203 실시예 14Example 14 화합물 14Compound 14 BH-3 BH-3 3.89 3.89 46.1 46.1 236236 실시예 15Example 15 화합물 15Compound 15 BH-3 BH-3 3.90 3.90 46.5 46.5 274274 실시예 16Example 16 화합물 16Compound 16 BH-3 BH-3 3.86 3.86 45.2 45.2 280280 실시예 17Example 17 화합물 17Compound 17 BH-3 BH-3 3.84 3.84 44.6 44.6 297297 실시예 18Example 18 화합물 18Compound 18 BH-3 BH-3 3.95 3.95 45.8 45.8 266266 실시예 19Example 19 화합물 19Compound 19 BH-3 BH-3 3.89 3.89 45.7 45.7 293293 실시예 20Example 20 화합물 20Compound 20 BH-3 BH-3 3.92 3.92 46.1 46.1 271271 비교예 1Comparative Example 1 BD-ABD-A BH-1 BH-1 3.89 3.89 41.9 41.9 100100 비교예 2Comparative Example 2 BD-BBD-B BH-1 BH-1 3.83 3.83 42.3 42.3 137137 비교예 3Comparative Example 3 BD-CBD-C BH-1 BH-1 3.85 3.85 42.5 42.5 123123 비교예 4Comparative Example 4 BD-DBD-D BH-1 BH-1 3.89 3.89 43.1 43.1 156156

실시예 21 내지 24 및 비교예 5Examples 21 to 24 and Comparative Example 5

상기 실시예 1에서 발광층의 도펀트로 상기 화합물 1 대신 하기 표 2에 기재된 화합물을 사용하고, 발광층의 호스트로 하기 표 2에 기재된 화합물을 사용한 것을 제외하고는 실시예 1과 동일한 방법을 이용하여 실시예 21 내지 실시예 24 및 비교예 5의 유기 발광 소자를 각각 제작하였다.In Example 1, the same method as in Example 1 was used, except that the compound shown in Table 2 was used instead of the compound 1 as the dopant of the light emitting layer, and the compound shown in Table 2 was used as the host of the light emitting layer. Organic light emitting devices of Examples 21 to 24 and Comparative Example 5 were fabricated, respectively.

상기 발광층의 제1 호스트와 제2 호스트의 중량비는 50 : 50 이다.The weight ratio of the first host and the second host of the emission layer is 50:50.

상기 실시예 21 내지 24 및 비교예 5의 유기 발광 소자에 10 mA/cm2의 전류 밀도를 인가할 때의 전압, 효율(cd/A/y) 및 20 mA/cm2의 전류 밀도를 인가할 때의 수명(T95)을 측정하고, 그 결과를 하기 표 1에 나타내었다. 이 때, T95는 전류 밀도 20 mA/cm2에서의 초기 휘도를 100%로 하였을 때 휘도가 95%로 감소되는데 소요되는 시간을 비교예 1을 기준으로 비율을 나타내었다. When applying a current density of 10 mA/cm 2 to the organic light emitting device of Examples 21 to 24 and Comparative Example 5, the voltage, efficiency (cd/A/y) and the current density of 20 mA/cm 2 were applied. The lifetime (T 95 ) of the time was measured, and the results are shown in Table 1 below. At this time, T 95 represents the ratio of the time required for the luminance to decrease to 95% when the initial luminance at a current density of 20 mA/cm 2 is 100%, based on Comparative Example 1.

EntryEntry 도펀트Dopant 제1 호스트First host 제2 호스트Second host 10 mA/cm2 10 mA / cm 2 20 mA/cm2 20 mA / cm 2 구동 전압 (V)Driving voltage (V) 환산 효율 (cd/A/y)Conversion efficiency (cd/A/y) T95 (%)T 95 (%) 실시예 21Example 21 화합물 5Compound 5 BH-1BH-1 BH-2BH-2 3.72 3.72 44.7 44.7 282282 실시예 22Example 22 화합물 7Compound 7 BH-1BH-1 BH-2BH-2 3.77 3.77 43.6 43.6 304304 실시예 23Example 23 화합물 9Compound 9 BH-1BH-1 BH-3BH-3 3.86 3.86 45.5 45.5 291291 실시예 24Example 24 화합물 13Compound 13 BH-2BH-2 BH-3BH-3 3.82 3.82 44.8 44.8 255255 비교예 5Comparative Example 5 BD-ABD-A BH-1BH-1 BH-2BH-2 3.81 3.81 42.2 42.2 129129

상기 환산 효율(cd/A/y)은 전류효율(cd/A)에서 재료의 색순도(CIEy)까지 고려한 것으로, 고휘도 및 고색 재현율을 목표로 하는 소형 및 대형 유기 발광 소자에서 중요한 효율의 기준값이 된다. The conversion efficiency (cd/A/y) considers from the current efficiency (cd/A) to the color purity (CIEy) of the material, and becomes an important efficiency reference value in small and large organic light emitting devices aiming at high luminance and high color reproducibility. .

표 1 및 2의 소자 결과에서 알 수 있듯이, 본 명세서의 일 실시상태에 따른 [화학식 1]로 표시되는 중수소로 치환된 탄소수 1 내지 3의 알킬기를 포함한 도펀트 물질을 이용하여 유기 발광 소자를 구성하였을 때, 그렇지 않은 소자보다 소자의 환산 효율과 수명 성능이 모두 우수하였다.As can be seen from the device results in Tables 1 and 2, the organic light emitting device was constructed using a dopant material including an alkyl group having 1 to 3 carbon atoms substituted with deuterium represented by [Chemical Formula 1] according to an exemplary embodiment of the present specification. At that time, both the conversion efficiency and lifetime performance of the device were superior to those of the other devices.

구체적으로, 본 발명 화학식 1의 화합물은 특정 위치에 중수소로 치환된 알킬기가 결합되는 것이 특징으로, 그렇지 않은 비교예 화합물 BD-A, BD-C 및 BD-D에 비하여, 효율이 최대 약 10% 정도 높고, 수명이 2배 내지 3배 정도 높은 결과를 나타내었다.Specifically, the compound of Formula 1 of the present invention is characterized in that an alkyl group substituted with deuterium is bonded at a specific position, and the efficiency is up to about 10% compared to the comparative compounds BD-A, BD-C and BD-D that are not otherwise. The results were high, and the lifespan was 2 to 3 times higher.

화합물이 여기된 상태에서는 화합물 내의 공명구조를 이루고 있는 전자들의 쏠림 현상이 일어나게 된다. 이때, 전자 밀도가 더 높아지거나 낮아지는 특정 위치에 알킬기를 치환시켜줌으로써 화합물의 발광 특성을 효과적으로 조율할 수 있다. 본 발명 화학식 1의 화합물과 같이 중수소로 치환된 알킬기를 도입하는 경우, 분자량을 크게 변화시키지 않고 화합물의 발광 특성을 효과적으로 조절 가능하게 되어 이를 사용한 소자는 효율 및 수명이 특히 우수한 결과를 나타내게 된다.When the compound is excited, electrons that make up the resonance structure in the compound are attracted. At this time, by substituting an alkyl group at a specific position where the electron density is higher or lower, the light emission characteristics of the compound can be effectively tuned. In the case of introducing an alkyl group substituted with deuterium, such as the compound of Formula 1 of the present invention, it is possible to effectively control the light-emitting characteristics of the compound without significantly changing the molecular weight, so that the device using the same exhibits particularly excellent results in efficiency and lifespan.

또한, 중수소로 치환된 탄소수 1 내지 3의 알킬기를 포함하는 화학식 1의 화합물은 중수소로 치환된 부틸기를 포함하는 비교예 BD-B에 비하여, 효율 및 수명이 우수한 효과를 나타내었다. In addition, the compound of Formula 1 including an alkyl group having 1 to 3 carbon atoms substituted with deuterium exhibited excellent effects in efficiency and life as compared to Comparative Example BD-B including a butyl group substituted with deuterium.

이는 탄소수 1 내지 3의 알킬 라디칼인 메틸 라디칼, 에틸 라디칼 및 프로필 라디칼이 (탄소수 4 이상의) 3차 탄소 라디칼인 부틸 라디칼에 비해 불안정하여, C(sp3)-C(sp2)의 결합이 파괴되며 일어나는 화합물의 분해 프로세스가 상대적으로 억제되어, 화합물 구조의 안정성이 확보되기 때문이다.This is because the methyl radical, ethyl radical, and propyl radical, which are alkyl radicals having 1 to 3 carbon atoms, are unstable compared to the butyl radical, which is a tertiary carbon radical (more than 4 carbon atoms), and the C(sp 3 )-C(sp 2 ) bond is destroyed This is because the decomposition process of the compound that occurs is relatively suppressed, and the stability of the compound structure is ensured.

Claims (20)

하기 화학식 1로 표시되는 화합물:Compound represented by the following formula (1): [화학식 1][Formula 1]
Figure PCTKR2020012249-appb-I000165
Figure PCTKR2020012249-appb-I000165
 상기 화학식 1에 있어서, In Formula 1, A1 및 A2는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 지방족 탄화수소고리; 치환 또는 비치환된 방향족 탄화수소고리; 치환 또는 비치환된 방향족 헤테로고리; 또는 치환 또는 비치환된 지방족 탄화수소고리 및 방향족 탄화수소고리의 축합고리이고,A1 and A2 are the same as or different from each other, and each independently a substituted or unsubstituted aliphatic hydrocarbon ring; A substituted or unsubstituted aromatic hydrocarbon ring; Substituted or unsubstituted aromatic heterocycle; Or a condensed ring of a substituted or unsubstituted aliphatic hydrocarbon ring and an aromatic hydrocarbon ring, X1 및 X2는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 또는 치환 또는 비치환된 알킬기이거나, -CRaRb-, -NRc-, -O-, -PRd-, -S-, -PORe-, -SO2-, -SiRfRg-, 또는 -BRh-를 통해 직접 연결되고, X1 and X2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group, or directly linked through -CRaRb-, -NRc-, -O-, -PRd-, -S-, -PORe-, -SO 2 -, -SiRfRg-, or -BRh- Become, Ra 내지 Rh는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 알키닐기; 치환 또는 비치환된 아릴알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 인접하는 기는 서로 결합하여 치환 또는 비치환된 고리를 형성하고,Ra To Rh are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups combine with each other to form a substituted or unsubstituted ring, R1 내지 R5는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아릴티옥시기; 치환 또는 비치환된 알킬티오기; 치환 또는 비치환된 아릴티오기; 치환 또는 비치환된 알킬술포닐기; 치환 또는 비치환된 아릴술포닐기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 알키닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 붕소기; 치환 또는 비치환된 아릴알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 인접하는 기는 서로 결합하여 치환 또는 비치환된 고리를 형성하고,R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkyl thioxy group; A substituted or unsubstituted arylthioxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfonyl group; A substituted or unsubstituted arylsulfonyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups combine with each other to form a substituted or unsubstituted ring, Y는 중수소로 치환된 탄소수 1 내지 3의 알킬기; 또는 하기 화학식 2로 표시되고,Y is an alkyl group having 1 to 3 carbon atoms substituted with deuterium; Or represented by the following formula (2), [화학식 2][Formula 2]
Figure PCTKR2020012249-appb-I000166
Figure PCTKR2020012249-appb-I000166
 상기 화학식 2에 있어서,In Formula 2, B1 및 B2는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 지방족 탄화수소 고리; 또는 치환 또는 비치환된 방향족 탄화수소 고리이고,B1 and B2 are the same as or different from each other, and each independently a substituted or unsubstituted aliphatic hydrocarbon ring; Or a substituted or unsubstituted aromatic hydrocarbon ring, R6 및 R7은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 알키닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 아릴알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 인접하는 기는 서로 결합하여 치환 또는 비치환된 고리를 형성하고,R6 and R7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkyl thioxy group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups combine with each other to form a substituted or unsubstituted ring, r1 및 r2는 서로 동일하거나 상이하고, 각각 독립적으로 1 내지 3의 정수이고,r1 and r2 are the same as or different from each other, and each independently an integer of 1 to 3, r3 및 r5 내지 r7는 서로 동일하거나 상이하고, 각각 독립적으로 1 내지 11의 정수이고,r3 and r5 to r7 are the same as or different from each other, and each independently an integer of 1 to 11, r4는 1 또는 2의 정수이고,r4 is an integer of 1 or 2, n은 1 또는 2의 정수이고,n is an integer of 1 or 2, r4+n는 2 또는 3의 정수이고,r4+n is an integer of 2 or 3, r1 내지 r7 및 n이 각각 2 이상인 경우, 각각의 괄호 안의 치환기는 서로 동일하거나 상이하고,When r1 to r7 and n are each 2 or more, the substituents in each parenthesis are the same as or different from each other, Y가 중수소로 치환된 탄소수 1 내지 3의 알킬기인 경우, X1, X2 및 R1 내지 R5 중 적어도 하나는 중수소로 치환된 탄소수 1 내지 3의 알킬기이고,When Y is an alkyl group having 1 to 3 carbon atoms substituted with deuterium, at least one of X1, X2 and R1 to R5 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium, Y가 상기 화학식 2로 표시되는 경우, X1, X2 및 R1 내지 R7 중 적어도 하나는 중수소로 치환된 탄소수 1 내지 3의 알킬기이고,When Y is represented by Formula 2, at least one of X1, X2 and R1 to R7 is an alkyl group having 1 to 3 carbon atoms substituted with deuterium,
Figure PCTKR2020012249-appb-I000167
는 화학식 1에 결합되는 위치를 의미한다.
Figure PCTKR2020012249-appb-I000167
Means a position bonded to the formula (1). 청구항 1에 있어서, The method according to claim 1, 상기 화학식 1은 하기 화학식 1-1 또는 1-2로 표시되는 것인 화합물:Formula 1 is a compound represented by the following Formula 1-1 or 1-2: [화학식 1-1][Formula 1-1]
Figure PCTKR2020012249-appb-I000168
Figure PCTKR2020012249-appb-I000168
 [화학식 1-2][Formula 1-2]
Figure PCTKR2020012249-appb-I000169
Figure PCTKR2020012249-appb-I000169
 상기 화학식 1-1 및 1-2에 있어서, In Formulas 1-1 and 1-2, R1 내지 R7, A1, A2, B1, B2, X1, X2 및 r1 내지 r7의 정의는 상기 화학식 1에서의 정의와 같고,The definitions of R1 to R7, A1, A2, B1, B2, X1, X2 and r1 to r7 are the same as those in Formula 1, Z는 중수소로 치환된 탄소수 1 내지 3의 알킬기이고,Z is an alkyl group having 1 to 3 carbon atoms substituted with deuterium, m은 1 또는 2의 정수이고, m이 2인 경우, Z는 서로 동일하거나 상이하고,m is an integer of 1 or 2, and when m is 2, Z is the same as or different from each other, r4+m은 2 또는 3의 정수이다.r4+m is an integer of 2 or 3. 청구항 1에 있어서, The method according to claim 1, 상기 A1 및 A2는 서로 동일하거나 상이하고, 각각 독립적으로 하기 화학식 A100 내지 A103 중 어느 하나로 표시되는 것인 화합물:Wherein A1 and A2 are the same as or different from each other, and each independently a compound represented by any one of the following formulas A100 to A103: [화학식 A100]　　　　　　[화학식 A101][Formula A100]　　　　　　[Formula A101]
Figure PCTKR2020012249-appb-I000170
Figure PCTKR2020012249-appb-I000170
 [화학식 A102]　　　　　　[화학식 A103][Formula A102]　　　　　　[Formula A103]
Figure PCTKR2020012249-appb-I000171
Figure PCTKR2020012249-appb-I000171
 상기 화학식 A100 내지 A103에 있어서,In the above formulas A100 to A103, G1은 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성하고,G1 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combined with an adjacent group to form a substituted or unsubstituted ring, X11은 O; S; 또는 CR101R102이고,X11 is O; S; Or CR101R102, R101 및 R102는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기이고,R101 and R102 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, g1은 0 내지 5의 정수이고, g1'은 0 내지 11의 정수이고, g1''은 0 내지 7의 정수이고, g1'''은 0 내지 11의 정수이고,g1 is an integer from 0 to 5, g1' is an integer from 0 to 11, g1'' is an integer from 0 to 7, and g1''' is an integer from 0 to 11, a1은 1 내지 2의 정수이고,a1 is an integer of 1 to 2, g1, g1', g1'' 및 g1'''이 각각 2 이상인 경우, 2 이상의 G1은 서로 동일하거나 상이하고,When g1, g1', g1'' and g1''' are each 2 or more, 2 or more G1s are the same as or different from each other,
Figure PCTKR2020012249-appb-I000172
는 화학식 1에 결합되는 위치를 의미한다.
Figure PCTKR2020012249-appb-I000172
Means a position bonded to the formula (1). 청구항 1에 있어서, The method according to claim 1, 상기 R1 또는 R2가 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성하는 경우, 상기 고리는 하기 화학식 C1 내지 C3 중 어느 하나로 표시되는 것인 화합물:When the R1 or R2 is bonded to each other with an adjacent group to form a substituted or unsubstituted ring, the ring is represented by any one of the following formulas C1 to C3: [화학식 C1]　　　　[화학식 C2]　　　[화학식 C3][Chemical Formula C1]　　　　[Chemical Formula C2]　　　[Chemical Formula C3]
Figure PCTKR2020012249-appb-I000173
Figure PCTKR2020012249-appb-I000173
 상기 화학식 C1 내지 C3에 있어서,In the above formulas C1 to C3, X21, X22 및 X31은 서로 동일하거나 상이하고, 각각 독립적으로, O; S; CP11P12; 또는 NP13이고,X21, X22 and X31 are the same as or different from each other, and each independently O; S; CP11P12; Or NP13, P1 및 P11 내지 P13은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성하고,P1 and P11 to P13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combined with an adjacent group to form a substituted or unsubstituted ring, b1은 1 내지 3의 정수이고,b1 is an integer of 1 to 3, p1은 0 내지 10의 정수이고, p2 및 p3는 각각 0 내지 4의 정수이고,p1 is an integer of 0 to 10, p2 and p3 are each an integer of 0 to 4, p1 내지 p3가 각각 2 이상인 경우, 2 이상의 P1은 서로 동일하거나 상이하고,When p1 to p3 are each 2 or more, 2 or more P1s are the same as or different from each other, *는 형성된 고리가 축합되는 위치를 의미한다.* Means the position where the formed ring is condensed. 청구항 1에 있어서, The method according to claim 1, 상기 화학식 2는 하기 화학식 201 내지 203 중 어느 하나로 표시되는 것인 화합물:Formula 2 is a compound represented by any one of the following Formulas 201 to 203: [화학식 201]　　　　　　　　[화학식 202]　　　　　　[화학식 203][Chemical Formula 201]　　　　　　　　[Chemical Formula 202]　　　　　　[Chemical Formula 203]
Figure PCTKR2020012249-appb-I000174
Figure PCTKR2020012249-appb-I000174
 상기 화학식 201 내지 203에 있어서,In Formulas 201 to 203, G6 및 G7은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 알킬티옥시기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 알키닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 아릴알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 인접하는 기와 서로 결합하여 치환 또는 비치환된 고리를 형성하고,G6 and G7 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkyl thioxy group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combined with an adjacent group to form a substituted or unsubstituted ring, G16 및 G17은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 또는 치환 또는 비치환된 알킬기이고,G16 and G17 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group, g6 및 g7는 각각 1 내지 5의 정수이고, g6' 및 g7'은 1 내지 4의 정수이고, g7''은 1 내지 8의 정수이고,g6 and g7 are each an integer of 1 to 5, g6' and g7' are an integer of 1 to 4, and g7'' is an integer of 1 to 8, g6, g7, g6', g7' 및 g7''이 각각 2 이상인 경우, 2 이상의 G6 및 G7은 각각 서로 동일하거나 상이하고,When g6, g7, g6', g7' and g7'' are each 2 or more, 2 or more G6 and G7 are each the same as or different from each other,
Figure PCTKR2020012249-appb-I000175
는 화학식 1에 결합되는 위치를 의미한다.
Figure PCTKR2020012249-appb-I000175
Means a position bonded to the formula (1). 청구항 1에 있어서,The method according to claim 1, 상기 화학식 1은 하기 화학식 1-3 내지 1-7 중 어느 하나로 표시되는 것인 화합물:Formula 1 is a compound represented by any one of the following Formulas 1-3 to 1-7: [화학식 1-3][Formula 1-3]
Figure PCTKR2020012249-appb-I000176
Figure PCTKR2020012249-appb-I000176
 [화학식 1-4][Formula 1-4]
Figure PCTKR2020012249-appb-I000177
Figure PCTKR2020012249-appb-I000177
 [화학식 1-5][Formula 1-5]
Figure PCTKR2020012249-appb-I000178
Figure PCTKR2020012249-appb-I000178
 [화학식 1-6][Formula 1-6]
Figure PCTKR2020012249-appb-I000179
Figure PCTKR2020012249-appb-I000179
 [화학식 1-7][Formula 1-7]
Figure PCTKR2020012249-appb-I000180
Figure PCTKR2020012249-appb-I000180
 상기 화학식 1-3 내지 1-7에 있어서,In Formulas 1-3 to 1-7, R1 내지 R7, X1, X2 및 r1 내지 r7의 정의는 상기 화학식 1에서의 정의와 같고,The definitions of R1 to R7, X1, X2 and r1 to r7 are the same as those in Formula 1, Z는 중수소로 치환된 탄소수 1 내지 3의 알킬기이고,Z is an alkyl group having 1 to 3 carbon atoms substituted with deuterium, m은 1 또는 2의 정수이고, m이 2인 경우, Z는 서로 동일하거나 상이하다.m is an integer of 1 or 2, and when m is 2, Z is the same as or different from each other. 청구항 1에 있어서, The method according to claim 1, 상기 화학식 1은 하기 화학식 1-8로 표시되는 것인 화합물:Formula 1 is a compound represented by the following Formula 1-8: [화학식 1-8][Formula 1-8]
Figure PCTKR2020012249-appb-I000181
Figure PCTKR2020012249-appb-I000181
 상기 화학식 1-8에 있어서,In Formula 1-8, A1, A2, R1 내지 R5, r1 내지 r5, Y 및 n의 정의는 화학식 1에서의 정의와 같고,The definitions of A1, A2, R1 to R5, r1 to r5, Y and n are the same as those in Formula 1, X3은 CRaRb, NRc, O, PRd, S, PORe, SO2, SiRfRg 또는 BRh이고,X3 is CRaRb, NRc, O, PRd, S, PORe, SO 2 , SiRfRg or BRh, Ra 내지 Rh는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 알키닐기; 치환 또는 비치환된 아릴알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 인접하는 기는 서로 결합하여 치환 또는 비치환된 고리를 형성한다.Ra To Rh are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring. 청구항 1에 있어서, The method according to claim 1, 상기 화학식 1은 하기 화학식 1-9 또는 1-10으로 표시되는 것인 화합물:Formula 1 is a compound represented by the following Formula 1-9 or 1-10: [화학식 1-9][Formula 1-9]
Figure PCTKR2020012249-appb-I000182
Figure PCTKR2020012249-appb-I000182
 [화학식 1-10][Formula 1-10]
Figure PCTKR2020012249-appb-I000183
Figure PCTKR2020012249-appb-I000183
 상기 화학식 1-9 및 1-10 에 있어서,In Formulas 1-9 and 1-10, X1, X2, A1, A2, R1, R3 내지 R5, r1, r3 내지 r5, Y 및 n의 정의는 화학식 1에서의 정의와 같고,The definitions of X1, X2, A1, A2, R1, R3 to R5, r1, r3 to r5, Y and n are the same as those in Formula 1, A3 및 A4는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 지방족 탄화수소 고리; 치환 또는 비치환된 방향족 탄화수소 고리; 치환 또는 비치환된 방향족 헤테로고리; 또는 치환 또는 비치환된 지방족 탄화수소고리 및 방향족 탄화수소고리의 축합고리이고,A3 and A4 are the same as or different from each other, and each independently a substituted or unsubstituted aliphatic hydrocarbon ring; A substituted or unsubstituted aromatic hydrocarbon ring; Substituted or unsubstituted aromatic heterocycle; Or a condensed ring of a substituted or unsubstituted aliphatic hydrocarbon ring and an aromatic hydrocarbon ring, R21 및 R22는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성하고,R21 and R22 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combined with an adjacent group to form a substituted or unsubstituted ring, r21 및 r22는 각각 1 내지 9의 정수이고,r21 and r22 are each an integer of 1 to 9, r21 및 r22가 각각 2 이상인 경우, 2 이상의 R21 및 R22는 각각 서로 같거나 상이하다.When r21 and r22 are each 2 or more, two or more R21 and R22 are each the same as or different from each other. 청구항 1에 있어서, The method according to claim 1, 상기 화학식 1은 하기 화학식 1-11 또는 1-12로 표시되는 것인 화합물:Formula 1 is a compound represented by the following Formula 1-11 or 1-12: [화학식 1-11][Formula 1-11]
Figure PCTKR2020012249-appb-I000184
Figure PCTKR2020012249-appb-I000184
 [화학식 1-12][Formula 1-12]
Figure PCTKR2020012249-appb-I000185
Figure PCTKR2020012249-appb-I000185
 상기 화학식 1-11 및 1-12에 있어서,In Formulas 1-11 and 1-12, X1, X2, R1 내지 R5, r1, r3, r4, A1, Y 및 n의 정의는 상기 화학식 1에서의 정의와 같고,The definitions of X1, X2, R1 to R5, r1, r3, r4, A1, Y and n are the same as those in Formula 1, X101은 직접결합; 또는 -BR103-이고,X101 is a direct bond; Or -BR103-, R103, G101 및 G102은 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기이고,R103, G101 and G102 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, r2' 는 1 또는 2이고,r2' is 1 or 2, r5'는 1 내지 4의 정수이고,r5' is an integer from 1 to 4, r5''는 1 내지 8의 정수이고,r5'' is an integer from 1 to 8, r2', r5' 및 r5''가 각각 2 이상인 경우, 2 이상의 R2 및 R5는 각각 서로 동일하거나 상이하다.When r2', r5' and r5'' are each 2 or more, two or more R2 and R5 are each the same as or different from each other. 청구항 1에 있어서,The method according to claim 1, 상기 Y는 -CD3; -C2D5; CH2CD3; CD(CD3)2 또는 CH(CD3)2인 것인 화합물.Y is -CD 3 ; -C 2 D 5 ; CH 2 CD 3 ; CD(CD 3 ) 2 or CH(CD 3 ) 2 The compound. 청구항 1에 있어서,The method according to claim 1, 상기 Y가 중수소로 치환된 탄소수 1 내지 3의 알킬기로 표시되는 경우, X1, X2 및 R1 내지 R5 중 적어도 2개는 중수소로 치환된 탄소수 1 내지 3의 알킬기인 것인 화합물.When the Y is represented by an alkyl group having 1 to 3 carbon atoms substituted with deuterium, at least two of X1, X2 and R1 to R5 are an alkyl group having 1 to 3 carbon atoms substituted with deuterium. 청구항 1에 있어서,The method according to claim 1, 상기 Y가 상기 화학식 2로 표시되는 경우, X1, X2 및 R1 내지 R7 중 적어도 2개는 중수소로 치환된 탄소수 1 내지 3의 알킬기인 것인 화합물.When Y is represented by Formula 2, at least two of X1, X2, and R1 to R7 are an alkyl group having 1 to 3 carbon atoms substituted with deuterium. 청구항 1에 있어서,The method according to claim 1, 상기 화학식 1은 하기 화합물 중 어느 하나로 표시되는 것인 화합물:Formula 1 is a compound represented by any one of the following compounds:
Figure PCTKR2020012249-appb-I000186
Figure PCTKR2020012249-appb-I000186
Figure PCTKR2020012249-appb-I000187
Figure PCTKR2020012249-appb-I000187
Figure PCTKR2020012249-appb-I000188
Figure PCTKR2020012249-appb-I000188
Figure PCTKR2020012249-appb-I000189
Figure PCTKR2020012249-appb-I000189
Figure PCTKR2020012249-appb-I000190
Figure PCTKR2020012249-appb-I000190
Figure PCTKR2020012249-appb-I000191
Figure PCTKR2020012249-appb-I000191
Figure PCTKR2020012249-appb-I000192
Figure PCTKR2020012249-appb-I000192
Figure PCTKR2020012249-appb-I000193
Figure PCTKR2020012249-appb-I000193
Figure PCTKR2020012249-appb-I000194
Figure PCTKR2020012249-appb-I000194
Figure PCTKR2020012249-appb-I000195
Figure PCTKR2020012249-appb-I000195
Figure PCTKR2020012249-appb-I000196
Figure PCTKR2020012249-appb-I000196
Figure PCTKR2020012249-appb-I000197
Figure PCTKR2020012249-appb-I000197
Figure PCTKR2020012249-appb-I000198
Figure PCTKR2020012249-appb-I000198
Figure PCTKR2020012249-appb-I000199
Figure PCTKR2020012249-appb-I000199
Figure PCTKR2020012249-appb-I000200
Figure PCTKR2020012249-appb-I000200
Figure PCTKR2020012249-appb-I000201
Figure PCTKR2020012249-appb-I000201
Figure PCTKR2020012249-appb-I000202
Figure PCTKR2020012249-appb-I000202
Figure PCTKR2020012249-appb-I000203
Figure PCTKR2020012249-appb-I000203
Figure PCTKR2020012249-appb-I000204
Figure PCTKR2020012249-appb-I000204
Figure PCTKR2020012249-appb-I000205
Figure PCTKR2020012249-appb-I000205
Figure PCTKR2020012249-appb-I000206
Figure PCTKR2020012249-appb-I000206
Figure PCTKR2020012249-appb-I000207
Figure PCTKR2020012249-appb-I000207
Figure PCTKR2020012249-appb-I000208
Figure PCTKR2020012249-appb-I000208
Figure PCTKR2020012249-appb-I000209
Figure PCTKR2020012249-appb-I000209
Figure PCTKR2020012249-appb-I000210
Figure PCTKR2020012249-appb-I000210
Figure PCTKR2020012249-appb-I000211
Figure PCTKR2020012249-appb-I000211
Figure PCTKR2020012249-appb-I000212
Figure PCTKR2020012249-appb-I000212
Figure PCTKR2020012249-appb-I000213
Figure PCTKR2020012249-appb-I000213
Figure PCTKR2020012249-appb-I000214
Figure PCTKR2020012249-appb-I000214
Figure PCTKR2020012249-appb-I000215
Figure PCTKR2020012249-appb-I000215
Figure PCTKR2020012249-appb-I000216
.
Figure PCTKR2020012249-appb-I000216
. 제1 전극; 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 청구항 1 내지 13 중 어느 한 항에 따른 화합물을 포함하는 것인 유기 발광 소자.A first electrode; A second electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers contains the compound according to any one of claims 1 to 13 Light-emitting element. 청구항 14에 있어서,The method of claim 14, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화합물을 포함하는 것인 유기 발광 소자.The organic material layer includes an emission layer, and the emission layer includes the compound. 청구항 14에 있어서,The method of claim 14, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 도펀트를 포함하고, 상기 도펀트는 상기 화합물을 포함하는 것인 유기 발광 소자.The organic material layer includes an emission layer, the emission layer includes a dopant, and the dopant includes the compound. 청구항 16에 있어서,The method of claim 16, 상기 발광층은 하기 화학식 H로 표시되는 화합물을 더 포함하는 것인 유기 발광 소자:The light emitting layer is an organic light emitting device further comprising a compound represented by the following formula (H): [화학식 H][Formula H]
Figure PCTKR2020012249-appb-I000217
Figure PCTKR2020012249-appb-I000217
 상기 화학식 H에 있어서,In Formula H, L20 및 L21은 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 2가의 헤테로고리기이고,L20 and L21 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group, Ar20 및 Ar21은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이고,Ar20 and Ar21 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, R20은 수소; 중수소; 할로겐기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이고,R20 is hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, r20은 0 내지 8의 정수이며, r20이 2이상인 경우, R20은 서로 동일하거나 상이하다.r20 is an integer from 0 to 8, and when r20 is 2 or more, R20 is the same as or different from each other. 청구항 16에 있어서,The method of claim 16, 상기 발광층은 호스트 화합물을 더 포함하고, 상기 호스트 화합물은 적어도 하나의 수소가 중수소로 치환된 것인 유기 발광 소자.The emission layer further includes a host compound, and the host compound is an organic light-emitting device in which at least one hydrogen is substituted with deuterium. 청구항 14에 있어서, The method of claim 14, 상기 유기물층은 전자주입층, 전자수송층, 또는 전자 주입 및 수송층을 포함하고, 상기 전자주입층, 전자수송층, 또는 전자 주입 및 수송층은 상기 화합물을 포함하는 것인 유기 발광 소자.The organic material layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer includes the compound. 청구항 14에 있어서,The method of claim 14, 상기 유기물층은 정공주입층, 정공수송층, 또는 정공 주입 및 수송층을 포함하고, 상기 정공주입층, 정공수송층, 또는 정공 주입 및 수송층은 상기 화합물을 포함하는 것인 유기 발광 소자.The organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer comprises the compound.
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