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WO2021029709A1 - Dispositif électroluminescent organique - Google Patents

Dispositif électroluminescent organique Download PDF

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WO2021029709A1
WO2021029709A1 PCT/KR2020/010782 KR2020010782W WO2021029709A1 WO 2021029709 A1 WO2021029709 A1 WO 2021029709A1 KR 2020010782 W KR2020010782 W KR 2020010782W WO 2021029709 A1 WO2021029709 A1 WO 2021029709A1
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차용범
허동욱
홍성길
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LG Chem Ltd
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Definitions

  • the present specification relates to an organic light emitting device.
  • the organic light-emitting device has a structure in which an organic thin film is disposed between two electrodes.
  • a voltage is applied to the organic light emitting device having such a structure, electrons and electrons injected from the two electrodes are combined in the organic thin film to form a pair and then emit light while disappearing.
  • the organic thin film may be composed of a single layer or multiple layers as necessary.
  • Materials used in organic light-emitting devices are pure organic materials or complex compounds in which organic materials and metals form a complex, and depending on the use, hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, etc. It can be classified as Here, as the hole injection material or the hole transport material, an organic material having a p-type property, that is, an organic material that is easily oxidized and has an electrochemically stable state during oxidation is mainly used. Meanwhile, as an electron injection material or an electron transport material, an organic material having an n-type property, that is, an organic material that is easily reduced and has an electrochemically stable state upon reduction is mainly used.
  • the light-emitting layer material a material having both p-type and n-type properties, that is, a material that is stable in both oxidation and reduction states, is preferable, and excitons generated by recombination of holes and electrons in the emission layer are formed.
  • a material having high luminous efficiency that converts it to light when it is formed is preferable.
  • Patent Document 1 Korean Patent Publication No. 10-2006-0009932
  • an organic light-emitting device having a low driving voltage, high efficiency and/or long life characteristics is described.
  • An emission layer provided between the first electrode and the second electrode
  • a first organic material layer provided between the first electrode and the emission layer
  • An organic light emitting device comprising a second organic material layer provided between the second electrode and the light emitting layer,
  • the first organic material layer includes a compound represented by Formula 1 below,
  • the second organic material layer provides an organic light emitting device including a compound represented by Formula 2 below.
  • Ar1 and Ar2 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with an alkyl group or an aryl group,
  • R1 is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,
  • n is an integer of 1 to 8, and when n is 2 or more, 2 or more R1s are the same as or different from each other,
  • L is a direct bond; A substituted or unsubstituted arylene group; A substituted or unsubstituted alkylene group; A substituted or unsubstituted divalent alkoxy group; A substituted or unsubstituted divalent alkenyl group; Or a substituted or unsubstituted heteroarylene group,
  • X1 is N; Or CR11, X2 is N; Or CR12, X3 is N; Or CR13,
  • At least one of X1 to X3 is N,
  • R11 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Cyano group; Nitro group; Hydroxy group; Carbonyl group; Ester group; Imide group; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl 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 alkyl sulfoxy group; Substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substitute
  • Ar3 and Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted arylalkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • the organic light-emitting device of the present invention includes a compound represented by Formula 1 in the first organic material layer and the compound represented by Formula 2 in the second organic material layer at the same time, thereby having a low driving voltage, high efficiency and/or long lifespan. Provides.
  • FIG. 1 shows an example of an organic light-emitting device including a substrate 1, an anode 2, an electron blocking layer 5, a light emitting layer 6, a hole blocking layer 7 and a cathode 9.
  • FIG. 2 shows a substrate (1), an anode (2), a hole injection layer (3), a hole transport layer (4), an electron blocking layer (5), a light emitting layer (6), a hole blocking layer (7), an electron transport and injection layer.
  • An example of an organic light-emitting device comprising (8) and a cathode (9) is shown.
  • Ar1 and Ar2 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with an alkyl group or an aryl group,
  • R1 is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,
  • n is an integer of 1 to 8, and when n is 2 or more, 2 or more R1s are the same as or different from each other,
  • L is a direct bond; A substituted or unsubstituted arylene group; A substituted or unsubstituted alkylene group; A substituted or unsubstituted divalent alkoxy group; A substituted or unsubstituted divalent alkenyl group; Or a substituted or unsubstituted heteroarylene group,
  • X1 is N; Or CR11, X2 is N; Or CR12, X3 is N; Or CR13,
  • At least one of X1 to X3 is N,
  • R11 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Cyano group; Nitro group; Hydroxy group; Carbonyl group; Ester group; Imide group; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl 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 alkyl sulfoxy group; Substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substitute
  • Ar3 and Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted arylalkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • 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; Cyano group; Nitro group; Imide group; Amide group; Carbonyl group; Ether group; Ester group; Hydroxy group; Alkyl group; Cycloalkyl group; Alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy group; Arylsulfoxy group; Alkenyl group; Silyl group; Boron group; Amine group; Arylphosphine group; Phosphine oxide group; Aryl group; And it is substituted with one or two or more substituents selected from the group consisting of a heteroaryl group, 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; Cyano group; Alkyl group; Cycloalkyl group; Silyl group; Aryl group; And it is substituted with one or two or more substituents selected from the group consisting of a heteroaryl group, two or more of the substituents exemplified above are substituted with a connected substituent, or does not have any substituents.
  • substituted or unsubstituted refers to deuterium; Cyano group; Alkyl group; Aryl group; And it is substituted with one or two or more substituents selected from the group consisting of a heteroaryl group, two or more of the substituents exemplified above are substituted with a connected substituent, or does not have any substituents.
  • examples of the halogen group include fluorine (-F), chlorine (-Cl), bromine (-Br), or iodine (-I).
  • the number of carbon atoms of the carbonyl group is not particularly limited, but it is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
  • the oxygen of the ester group is an alkyl group having 1 to 25 carbon atoms; An alkenyl group having 1 to 25 carbon atoms; Aryl group having 6 to 30 carbon atoms; Or it may be substituted with a heterocyclic group having 2 to 30 carbon atoms.
  • the oxygen is an alkyl group having 1 to 10 carbon atoms; An alkenyl group having 1 to 10 carbon atoms; Aryl group having 6 to 20 carbon atoms; Or it is substituted with a C2-C20 heterocyclic group.
  • the number of carbon atoms of the imide group is not particularly limited, but it is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
  • the nitrogen of the amide group may be substituted with hydrogen, a straight-chain, branched or cyclic alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
  • 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, etc., 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, a phenyl boron group, but is not limited thereto.
  • the alkyl group may be a linear or branched chain, 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 linear, branched or cyclic.
  • the number of carbon atoms of the alkoxy group is not particularly limited, but it is preferably 1 to 20 carbon atoms.
  • the alkenyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but 2 to 30; 2 to 20; 2 to 10; Or it is preferably 2 to 5.
  • Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but are not limited thereto.
  • Substituents including an alkyl group, an alkoxy group, and other alkyl group moieties described in the present specification include all of a straight chain or a 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 number of carbon atoms of the cycloalkyl group is 3 to 20. 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, and the like, but are 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 with 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 alkyl group in the alkylthioxy group and the alkylsulfoxy group is the same as the example of the alkyl group described above.
  • the alkyl thioxy group includes a methyl thioxy group, an ethyl thioxy group, a tert-butyl thioxy group, a hexyl thioxy group, an octyl thioxy group
  • the alkyl sulfoxy group is a methyl sulfoxy group, an ethyl sulfoxy group, a propyl sulfoxy group, and butyl.
  • sulfoxy groups are not limited thereto.
  • 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, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenyl group, chrysenyl group, fluorenyl group, triphenylenyl group, etc., 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.
  • the aryl group in the arylthioxy group and the arylsulfoxy group is the same as the example of the aryl group described above.
  • the heterocyclic group is a cyclic group including one or more of elements such as N, O, P, S, Si, and Se as a hetero atom, 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 a pyridine group, a pyrrole group, a pyrimidine group, a quinoline group, a pyridazinyl group, a furan group, a thiophene group, an imidazole group, a pyrazole group, a dibenzofuran group, a dibenzothiophene group , Carbazole group, benzocarbazole group, naphthobenzofuran group, benzonaphthothiophene group, indenocarbazole group, triazinyl group, etc., 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 for the divalent group.
  • the meaning of bonding with adjacent groups to form a ring means a substituted or unsubstituted aliphatic hydrocarbon ring by bonding with adjacent groups;
  • the hydrocarbon ring refers to a ring consisting only of carbon and hydrogen atoms.
  • the heterocycle refers to a ring containing at least one selected from elements such as N, O, P, S, Si and Se.
  • the aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic hetero ring and aromatic hetero ring may be monocyclic or polycyclic.
  • the aliphatic hydrocarbon ring is a ring that is not aromatic and refers to a ring consisting only of carbon and hydrogen atoms.
  • Examples of the aliphatic hydrocarbon ring 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 refers to 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 refers to an aliphatic ring containing at least one heteroatom.
  • aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxephan, 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
  • aryl group may be applied except that the arylene group is divalent.
  • heteroarylene group is divalent
  • description of the heteroaryl group may be applied.
  • Ar1 and Ar2 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with an alkyl group or an aryl group,
  • R1 is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,
  • n is an integer of 1 to 8, and when n is 2 or more, 2 or more R1s are the same as or different from each other.
  • Ar1 and Ar2 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with an alkyl group or an aryl group.
  • Ar1 and Ar2 are the same as or different from each other, and are each independently a monocyclic to tetracyclic aryl group unsubstituted or substituted with an alkyl group or a monocyclic to tetracyclic aryl group.
  • Ar1 and Ar2 are the same as or different from each other, and are each independently a monocyclic to tricyclic aryl group unsubstituted or substituted with an alkyl group or a monocyclic to tricyclic aryl group.
  • Ar1 and Ar2 are the same as or different from each other, and each independently a monocyclic to bicyclic aryl group unsubstituted or substituted with an alkyl group or a monocyclic to bicyclic aryl group.
  • Ar1 and Ar2 are the same as or different from each other, and are each independently an aryl group having 6 to 60 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 60 carbon atoms or an aryl group having 6 to 60 carbon atoms.
  • Ar1 and Ar2 are the same as or different from each other, and are each independently an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms.
  • Ar1 and Ar2 are the same as or different from each other, and are each independently an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 20 carbon atoms.
  • Ar1 and Ar2 are the same as or different from each other, and are each independently an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 14 carbon atoms.
  • Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with an alkyl group or an aryl group; A biphenyl group unsubstituted or substituted with an alkyl group or an aryl group; A naphthyl group unsubstituted or substituted with an alkyl group or an aryl group; A phenanthrenyl group unsubstituted or substituted with an alkyl group or an aryl group; Terphenyl group unsubstituted or substituted with an alkyl group or an aryl group; Or a fluorenyl group unsubstituted or substituted with an alkyl group or an aryl group.
  • Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with an aryl group; A biphenyl group unsubstituted or substituted with an aryl group; A naphthyl group unsubstituted or substituted with an aryl group; A phenanthrenyl group unsubstituted or substituted with an aryl group; Terphenyl group unsubstituted or substituted with an aryl group; Or a fluorenyl group unsubstituted or substituted with an alkyl group or an aryl group.
  • Ar1 and Ar2 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 14 carbon atoms; A biphenyl group unsubstituted or substituted with an aryl group having 6 to 14 carbon atoms; A naphthyl group unsubstituted or substituted with an aryl group having 6 to 14 carbon atoms; A phenanthrenyl group unsubstituted or substituted with an aryl group having 6 to 14 carbon atoms; Terphenyl group unsubstituted or substituted with an aryl group having 6 to 14 carbon atoms; Or a fluorenyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 14 carbon atoms.
  • Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a methyl group, a phenyl group, a naphthyl group, or a phenanthrenyl group;
  • a biphenyl group unsubstituted or substituted with a methyl group, a phenyl group, a naphthyl group, or a phenanthrenyl group;
  • a naphthyl group unsubstituted or substituted with a methyl group, a phenyl group, a naphthyl group, or a phenanthrenyl group;
  • a phenanthrenyl group unsubstituted or substituted with a methyl group, a phenyl group, a naphthyl group, or a phenanthrenyl group;
  • a terphenyl group unsubstituted or substituted with a methyl group,
  • Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; A biphenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; A naphthyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; A phenanthrenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; A terphenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; Or
  • Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; Biphenyl group; Naphthyl group; Phenanthrenyl group; Terphenyl group; Or a fluorenyl group unsubstituted or substituted with a methyl group.
  • Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; Biphenyl group; Phenanthrenyl group; Terphenyl group; Or a dimethyl fluorenyl group.
  • Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; Biphenyl group; Terphenyl group; Or a dimethyl fluorenyl group.
  • Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; Biphenyl group; Or terphenyl group.
  • Ar1 and Ar2 are the same as or different from each other, and each may be independently selected from the following structures.
  • the dotted line indicates the bonding position.
  • R6 is an alkyl group or an aryl group.
  • R6 is an alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms.
  • R6 is an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 20 carbon atoms.
  • R6 is a methyl group or a phenyl group.
  • R6 is a methyl group.
  • Ar1 and Ar2 are the same as or different from each other, and each may be independently selected from the following structures.
  • the dotted line indicates the bonding position.
  • Ar1 is represented by -L101-Ar101
  • Ar2 is represented by -L102-Ar102.
  • L101 and L102 are the same as or different from each other, and each independently a direct bond; Or an arylene group.
  • L101 and L102 are the same as or different from each other, and each independently a direct bond; Or an arylene group having 6 to 60 carbon atoms.
  • L101 and L102 are the same as or different from each other, and each independently a direct bond; Or an arylene group having 6 to 30 carbon atoms.
  • L101 and L102 are the same as or different from each other, and each independently a direct bond; Or an arylene group having 6 to 20 carbon atoms.
  • L101 and L102 are the same as or different from each other, and each independently a direct bond; Phenylene group; Or a biphenylene group.
  • L101 and L102 are the same as or different from each other, and each independently a direct bond; Or a phenylene group.
  • Ar101 and Ar102 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with an alkyl group or an aryl group.
  • Ar101 and Ar102 are the same as or different from each other, and each independently an aryl group having 6 to 60 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 60 carbon atoms or an aryl group having 6 to 60 carbon atoms.
  • Ar101 and Ar102 are the same as or different from each other, and are each independently an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms.
  • Ar101 and Ar102 are the same as or different from each other, and are each independently an aryl group having 6 to 20 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 20 carbon atoms.
  • Ar101 and Ar102 are the same as or different from each other, and each independently an alkyl group or a monocyclic to tetracyclic aryl group unsubstituted or substituted with a monocyclic to tetracyclic aryl group.
  • Ar101 and Ar102 are the same as or different from each other, and each independently an alkyl group or a monocyclic to tricyclic aryl group unsubstituted or substituted with a monocyclic to tricyclic aryl group.
  • Ar101 and Ar102 are the same as or different from each other, and each independently a monocyclic to bicyclic aryl group unsubstituted or substituted with an alkyl group or a monocyclic to bicyclic aryl group.
  • Ar101 and Ar102 are the same as or different from each other, and each independently an alkyl group or an aryl group substituted or unsubstituted phenyl group; A biphenyl group unsubstituted or substituted with an alkyl group or an aryl group; A naphthyl group unsubstituted or substituted with an alkyl group or an aryl group; A phenanthrenyl group unsubstituted or substituted with an alkyl group or an aryl group; Terphenyl group unsubstituted or substituted with an alkyl group or an aryl group; Or a fluorenyl group unsubstituted or substituted with an alkyl group or an aryl group.
  • Ar101 and Ar102 are the same as or different from each other, and each independently a methyl group, a phenyl group, a naphthyl group, or a phenyl group unsubstituted or substituted with a phenanthrenyl group;
  • a biphenyl group unsubstituted or substituted with a methyl group, a phenyl group, a naphthyl group, or a phenanthrenyl group;
  • a naphthyl group unsubstituted or substituted with a methyl group, a phenyl group, a naphthyl group, or a phenanthrenyl group;
  • a phenanthrenyl group unsubstituted or substituted with a methyl group, a phenyl group, a naphthyl group, or a phenanthrenyl group;
  • a terphenyl group unsubstituted or substituted with a methyl group,
  • Ar101 and Ar102 are the same as or different from each other, and each independently a phenyl group, a naphthyl group, or a phenyl group unsubstituted or substituted with a phenanthrenyl group; A biphenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; A naphthyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; A phenanthrenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; A terphenyl group unsubstituted or substituted with a phenyl group, a naphthyl group, or a phenanthrenyl group; Or
  • Ar101 and Ar102 are the same as or different from each other, and each independently a phenyl group, a naphthyl group, or a phenyl group unsubstituted or substituted with a phenanthrenyl group; Biphenyl group; Naphthyl group; Phenanthrenyl group; Terphenyl group; Or a fluorenyl group unsubstituted or substituted with a methyl group.
  • Ar101 and Ar102 are the same as or different from each other, and each independently a phenyl group, a naphthyl group, or a phenyl group unsubstituted or substituted with a phenanthrenyl group; Biphenyl group; Naphthyl group; Phenanthrenyl group; Terphenyl group; Or a dimethyl fluorenyl group.
  • Ar101 and Ar102 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Phenanthrenyl group; Or a fluorenyl group unsubstituted or substituted with a methyl group.
  • Ar101 and Ar102 are the same as or different from each other, and each independently a phenyl group; Naphthyl group; Or a phenanthrenyl group.
  • R1 is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted C1-C30 alkyl group; Or a substituted or unsubstituted aryl group having 6 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.
  • R1 is hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted C1 to C20 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or adjacent groups are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 20 carbon atoms.
  • R1 is hydrogen; Or deuterium, or by bonding with adjacent groups to form an aromatic hydrocarbon ring condensed in the carbazole.
  • R1 is hydrogen, or is combined with an adjacent group to form an aromatic hydrocarbon ring condensed in carbazole.
  • R1 is hydrogen, or combines with an adjacent group to form a benzene ring condensed with carbazole.
  • R1 is hydrogen
  • R1 is combined with an adjacent group to form a benzene ring condensed with carbazole.
  • n is an integer of 1 to 8, and when n is 2 or more, two or more R1s are the same as or different from each other.
  • n 1
  • n is 2.
  • n 8.
  • Formula 1 is represented by the following Formula 1-1 or 1-2.
  • Formula 1 is represented by any one of the following Formulas 1-3 to 1-6.
  • G1 and G2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
  • g1 is an integer from 1 to 10
  • g2 is an integer from 1 to 8
  • g1 is 2 or more, two or more G1s are the same as or different from each other, and when g2 is 2 or more, two or more G2s are the same or different from each other.
  • G1 and G2 are the same as or different from each other, and hydrogen; Or deuterium.
  • G1 and G2 are hydrogen.
  • g1 is 1.
  • g1 is 10.
  • g2 is 1.
  • g2 is 8.
  • the compound represented by Formula 1 is represented by any one of the following structural formulas.
  • L is a direct bond; A substituted or unsubstituted arylene group; A substituted or unsubstituted alkylene group; A substituted or unsubstituted divalent alkoxy group; A substituted or unsubstituted divalent alkenyl group; Or a substituted or unsubstituted heteroarylene group,
  • X1 is N; Or CR11, X2 is N; Or CR12, X3 is N; Or CR13,
  • At least one of X1 to X3 is N,
  • R11 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Cyano group; Nitro group; Hydroxy group; Carbonyl group; Ester group; Imide group; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl 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 alkyl sulfoxy group; Substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substitute
  • Ar3 and Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted arylalkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • L is a direct bond; A substituted or unsubstituted arylene group; A substituted or unsubstituted alkylene group; A substituted or unsubstituted divalent alkoxy group; A substituted or unsubstituted divalent alkenyl group; Or a substituted or unsubstituted heteroarylene group.
  • L is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.
  • L is a direct bond; Or a substituted or unsubstituted arylene group.
  • L is a direct bond; Or a substituted or unsubstituted C6 to C60 arylene group.
  • L is a direct bond; Or a substituted or unsubstituted C 6 to C 30 arylene group.
  • L is a direct bond; Or a substituted or unsubstituted C6 to C20 arylene group.
  • L is a direct bond; Or a substituted or unsubstituted C6 to C12 arylene group.
  • L is a direct bond; Or a substituted or unsubstituted C6 to C10 arylene group.
  • L is a direct bond; A substituted or unsubstituted phenylene group; Or a substituted or unsubstituted biphenylene group.
  • L is a direct bond; Phenylene group; Or a biphenylene group.
  • L is a direct bond; Or a phenylene group.
  • L may be a direct bond or may be selected from one of the following structural formulas.
  • the dotted line indicates the bonding position.
  • R101 to R103 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
  • R101 to R103 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 to R103 are the same as or different from each other, and each independently a methyl group or a phenyl group.
  • R101 and R102 are the same as or different from each other, and each independently a methyl group or a phenyl group.
  • R103 is a phenyl group.
  • L may be a direct bond or may be selected from one of the following structural formulas.
  • X1 is N; Or CR11, X2 is N; Or CR12, X3 is N; Or CR13, and at least one of X1 to X3 is N.
  • At least one of X1 to X3 is N.
  • At least two of X1 to X3 are N.
  • X1, X2, and X3 are N.
  • X1 and X2 are N, and X3 is CR13.
  • X1 and X3 are N, and X2 is CR12.
  • X2 and X3 are N, and X1 is CR11.
  • X1 is N
  • X2 is CR12
  • X3 is CR13.
  • X2 is N
  • X1 is CR11
  • X3 is CR13.
  • X3 is N
  • X1 is CR11
  • X2 is CR12.
  • R11 to R13 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 heteroaryl group.
  • R11 to R13 are the same as or different from each other, and each independently 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.
  • R11 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted C2 to C20 heteroaryl group.
  • R11 to R13 are hydrogen; Or deuterium.
  • R11 to R13 are hydrogen.
  • Ar3 and Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted arylalkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • Ar3 and Ar4 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 heteroaryl group.
  • Ar3 and Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C2 to C60 heteroaryl group.
  • Ar3 and Ar4 are the same as or different from each other, and each independently 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.
  • Ar3 and Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted C2 to C20 heteroaryl group.
  • Ar3 and Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 15 carbon atoms; Or a substituted or unsubstituted C 2 to C 15 heteroaryl group.
  • Ar3 and Ar4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 10 carbon atoms; Or a substituted or unsubstituted C2 to C10 heteroaryl group.
  • Ar3 and Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic to 6-cyclic aryl group; Or a substituted or unsubstituted monocyclic to 6 ring heteroaryl group.
  • Ar3 and Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic to 5-cyclic aryl group; Or a substituted or unsubstituted monocyclic to 5-cyclic heteroaryl group.
  • Ar3 and Ar4 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 heteroaryl group.
  • Ar3 and Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic to tricyclic aryl group; Or a substituted or unsubstituted monocyclic to tricyclic heteroaryl group.
  • Ar3 and Ar4 are the same as or different from each other, and each independently at least one group selected from the group consisting of deuterium, a halogen group, a cyano group, a silyl group, an alkyl group, and an aryl group, or two of the aforementioned substituents.
  • aryl group unsubstituted or substituted with a group connected above; Or a heteroaryl group unsubstituted or substituted with at least one group selected from the group consisting of deuterium, a halogen group, a cyano group, a silyl group, an alkyl group and an aryl group, or a group to which two or more of the aforementioned substituents are connected.
  • Ar3 and Ar4 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with a cyano group, an alkyl group, or an aryl group; Or a cyano group, an alkyl group or an aryl group substituted or unsubstituted heteroaryl group.
  • Ar3 and Ar4 are the same as or different from each other, and each independently a cyano group, an alkyl group having 1 to 30 carbon atoms, or an aryl having 6 to 30 carbon atoms unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms. group; Or a cyano group, a C1-C30 alkyl group, or a C2-C30 heteroaryl group unsubstituted or substituted with a C6-C30 aryl group.
  • Ar3 and Ar4 are the same as or different from each other, and each independently a cyano group, an alkyl group having 1 to 20 carbon atoms, or an aryl having 6 to 20 carbon atoms unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms group; Or a cyano group, a C1-C20 alkyl group, or a C2-C20 heteroaryl group unsubstituted or substituted with a C6-C20 aryl group.
  • Ar3 and Ar4 are the same as or different from each other, and each independently a cyano group, an alkyl group having 1 to 5 carbon atoms, or an aryl having 6 to 20 carbon atoms unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms group; Or a cyano group, an alkyl group having 1 to 5 carbon atoms, or a heteroaryl group having 2 to 20 carbon atoms unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms.
  • Ar3 and Ar4 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 phenanthrenyl group; A substituted or unsubstituted triphenylenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted spirobifluorenyl group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group.
  • Ar3 and Ar4 are the same as or different from each other, and each independently at least one group selected from the group consisting of deuterium, a halogen group, a cyano group, a silyl group, an alkyl group, and an aryl group, or two of the aforementioned substituents.
  • Ar3 and Ar4 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Phenanthrenyl group; Triphenylenyl group; Fluorenyl group; Spirobifluorenyl group; Dibenzofuran group; Dibenzothiophene group; Or a carbazole group, and the groups may be unsubstituted or substituted with one or more groups from the group consisting of deuterium, halogen group, cyano group, alkylsilyl group, alkyl group and aryl group.
  • Ar3 and Ar4 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a cyano group, an alkyl group, or an aryl group; A biphenyl group unsubstituted or substituted with a cyano group, an alkyl group or an aryl group; A terphenyl group unsubstituted or substituted with a cyano group, an alkyl group or an aryl group; A naphthyl group unsubstituted or substituted with a cyano group, an alkyl group or an aryl group; A phenanthrenyl group unsubstituted or substituted with a cyano group, an alkyl group or an aryl group; A triphenylenyl group unsubstituted or substituted with a cyano group, an alkyl group or an aryl group; A fluorenyl group
  • Ar3 and Ar4 are the same as or different from each other, and each independently a cyano group, an alkyl group having 1 to 20 carbon atoms, or a phenyl group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms;
  • Ar3 and Ar4 are the same as or different from each other, and each independently a cyano group, a methyl group, a phenyl group, a naphthyl group, or a phenyl group unsubstituted or substituted with a phenanthrenyl group;
  • a biphenyl group unsubstituted or substituted with a cyano group, a methyl group, a phenyl group, a naphthyl group, or a phenanthrenyl group;
  • a terphenyl group unsubstituted or substituted with a cyano group, a methyl group, a phenyl group, a naphthyl group, or a phenanthrenyl group;
  • a naphthyl group unsubstituted or substituted with a cyano group, a methyl group, a phenyl group, a naphthyl group, or a phenanthrenyl group
  • Ar3 and Ar4 are the same as or different from each other, and each independently a cyano group, a methyl group, a phenyl group, a naphthyl group, or a phenyl group unsubstituted or substituted with a phenanthrenyl group; Biphenyl group; Terphenyl group; A naphthyl group unsubstituted or substituted with a phenyl group; Phenanthrenyl group; Triphenylenyl group; A fluorenyl group unsubstituted or substituted with a methyl group or a phenyl group; Spirobifluorenyl group; Dibenzofuran group; Dibenzothiophene group; Or a carbazole group unsubstituted or substituted with a phenyl group or a naphthyl group.
  • Ar3 and Ar4 are the same as or different from each other, and each independently a phenyl group or a phenyl group unsubstituted or substituted with a naphthyl group; Biphenyl group; Or terphenyl group.
  • Ar3 and Ar4 are the same as or different from each other, and each may be independently selected from the following structures.
  • the structure is unsubstituted or substituted with a cyano group or an alkyl group, and the dotted line indicates a bonding position.
  • the structure is unsubstituted or substituted with a cyano group or a methyl group.
  • R6 is a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.
  • R6 is 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.
  • R6 is 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.
  • R6 is a methyl group; Or a phenyl group.
  • R7 is a substituted or unsubstituted aryl group.
  • R7 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • R7 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
  • R7 is a substituted or unsubstituted phenyl group; Or a substituted or unsubstituted naphthyl group.
  • R7 is a phenyl group; Or a naphthyl group.
  • any one of Ar3 and Ar4 is a substituted or unsubstituted aryl group, and the other is a substituted or unsubstituted heteroaryl group.
  • Ar3 and Ar4 are a substituted or unsubstituted aryl group, and are different from each other.
  • Chemical Formula 2 is represented by any one of Chemical Formulas 2-1 to 2-4 below.
  • the compound represented by Formula 2 is represented by any one of the following structural formulas.
  • 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.
  • a first organic material layer is formed between the first electrode and the emission layer using the compound of Formula 1
  • a second organic material layer is formed between the second electrode and the emission layer using the compound of Formula 2. Except for this, it can be manufactured by a conventional method and material for manufacturing an organic light emitting device.
  • the compound 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, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.
  • the organic material layer of the organic light emitting device of the present invention 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 of the present invention includes one or more of a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron transport and injection layer as an organic material layer. It can have a structure to However, the structure of the organic light emitting device is not limited thereto, and may include a smaller number or a larger number of organic material layers.
  • the organic light-emitting device of the present invention includes a light-emitting layer, the first organic material layer provided between the first electrode and the light-emitting layer is represented by the compound represented by Formula 1, and the second organic material layer provided between the second electrode and the light-emitting layer is represented by formula 2. It includes a compound that becomes.
  • the thickness of the organic material layer including the compound of Formula 1 is 30 ⁇ to 300 ⁇ , preferably 50 ⁇ to 200 ⁇ .
  • the thickness of the organic material layer including the compound of Formula 2 is 30 ⁇ to 200 ⁇ , preferably 50 ⁇ to 100 ⁇ .
  • the first organic material layer provided between the first electrode and the light emitting layer of the organic light emitting device of the present invention 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 the transport layer includes the compound represented by Chemical Formula 1.
  • the first organic material layer provided between the first electrode and the light emitting layer of the organic light emitting device of the present invention may be a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, a hole transport layer, or a hole injection layer.
  • the transport layer may include a compound represented by Chemical Formula 1.
  • the first organic material layer provided between the first electrode and the emission layer of the organic light emitting device of the present invention includes an electron blocking layer, and the electron blocking layer includes the compound represented by Formula 1 above.
  • the first organic material layer provided between the first electrode and the emission layer of the organic light emitting device of the present invention may be an electron blocking layer, and the electron blocking layer may include a compound represented by Formula 1 above.
  • the second organic material layer provided between the second electrode and the emission layer of the organic light emitting device of the present invention 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 the transport layer includes the compound represented by Chemical Formula 1.
  • the second organic material layer provided between the second electrode and the emission layer of the organic light emitting device of the present invention may be 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 layer.
  • the transport layer may include a compound represented by Chemical Formula 1.
  • the second organic material layer provided between the second electrode and the emission layer of the organic light emitting device of the present invention includes a hole blocking layer, and the hole blocking layer includes a compound represented by Formula 2.
  • the second organic material layer provided between the second electrode and the emission layer of the organic light emitting device of the present invention may be a hole blocking layer, and the hole blocking layer may include the compound represented by Formula 2.
  • the first organic material layer may further include other organic compounds, metals, or metal compounds in addition to the compound represented by Chemical Formula 1.
  • the second organic material layer may further include other organic compounds, metals, or metal compounds in addition to the compound represented by Chemical Formula 2.
  • the organic light emitting device of the present invention further comprises at least one organic material layer among a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole transport and injection layer.
  • I can.
  • the first organic material layer is in contact with the emission layer.
  • the meaning of contact means that no other organic material layer exists between the light emitting layer and the first organic material layer.
  • the second organic material layer is in contact with the emission layer.
  • the meaning of contact means that no other organic material layer exists between the light emitting layer and the second organic material layer.
  • the organic material layer may include an electron blocking layer, and a material known in the art may be used for the electron blocking layer.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode
  • the second electrode is an anode
  • the organic light-emitting device may have, for example, a stacked structure as described below, but is not limited thereto.
  • the structure of the organic light-emitting device of the present invention may have a structure as shown in FIGS. 1 and 2, but is not limited thereto.
  • FIG. 1 illustrates a structure of an organic light-emitting device in which a substrate 1, an anode 2, an electron blocking layer 5, a light emitting layer 6, a hole blocking layer 7 and a cathode 9 are sequentially stacked.
  • the compound represented by Formula 1 and the compound represented by Formula 2 may be included in the electron blocking layer 5, the light emitting layer 6, or the hole blocking layer 7.
  • FIG. 2 shows a substrate (1), an anode (2), a hole injection layer (3), a hole transport layer (4), an electron blocking layer (5), a light emitting layer (6), a hole blocking layer (7), an electron transport and injection layer.
  • the structure of an organic light-emitting device in which (8) and a cathode (9) are sequentially stacked is illustrated.
  • the compound represented by Formula 1 and the compound represented by Formula 2 are the hole injection layer (3), hole transport layer (4), electron blocking layer (5), light emitting layer (6), and hole blocking. It may be included in the layer 7 or the electron transport and injection layer 8.
  • the organic light-emitting device uses a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, and uses a metal or conductive metal oxide or alloy thereof on a substrate.
  • PVD physical vapor deposition
  • an anode formed by forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, an electron transport layer and an electron injection 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 organic material layer may further include at least one of a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole transport and injection layer.
  • the organic material layer may have a multilayer structure including a hole injection layer, a hole transport layer, a layer for simultaneously injecting and transporting electrons, an electron blocking layer, a light emitting layer and an electron transport layer, an electron injection layer, an electron transport and injection layer, etc. It may not have a single layer structure.
  • the organic material layer is made of a variety of polymer materials, and is used in a smaller number of solvent processes, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer. It can be made in layers.
  • the anode is an electrode for injecting holes, and a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer as the anode material.
  • the cathode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO 2: a combination of a metal and an oxide such as Sb; Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto.
  • the cathode is an electrode for injecting electrons
  • the cathode material is usually a material having a small work function to facilitate electron injection into the organic material layer.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; There are multi-layered materials such as LiF/Al or LiO 2 /Al, but are not limited thereto.
  • the hole injection layer is a layer that facilitates injection of holes from the anode to the light emitting layer
  • the hole injection material is a material capable of receiving holes from the anode at a low voltage, and is a high occupied HOMO (highest occupied material) of the hole injection material. It is preferable that molecular orbital) is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • hole injection materials include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances.
  • the thickness of the hole injection layer may be 1 to 150 nm.
  • the thickness of the hole injection layer is 1 nm or more, there is an advantage of preventing deterioration of the hole injection characteristics, and when the thickness of the hole injection layer is 150 nm or less, the thickness of the hole injection layer is too thick to increase the driving voltage to improve the movement of holes. There is an advantage that can prevent it.
  • the hole transport layer may serve to facilitate transport of holes.
  • the hole transport material a material capable of transporting holes from the anode or the hole injection layer and transferring them to the emission layer, and a material having high mobility for holes is suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer including a conjugated portion and a non-conjugated portion, but are not limited thereto.
  • a hole buffer layer may be additionally provided between the hole injection layer and the hole transport layer, and may include a hole injection or transport material known in the art.
  • An electron blocking layer may be provided between the hole transport layer and the light emitting layer.
  • the above-described compound or a material known in the art may be used for the electron blocking layer.
  • the emission layer may emit red, green, or blue light, and may be made of a phosphorescent material or a fluorescent material.
  • the light-emitting material is a material capable of emitting light in a visible light region by transporting and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable.
  • Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole, and benzimidazole-based compounds; Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.
  • Alq 3 8-hydroxy-quinoline aluminum complex
  • Carbazole-based compounds Dimerized styryl compounds
  • BAlq 10-hydroxybenzo quinoline-metal compound
  • Benzoxazole, benzthiazole, and benzimidazole-based compounds include Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.
  • Examples of the host material for the light emitting layer include condensed aromatic ring derivatives or heterocyclic compounds.
  • 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, and the like, but are not limited thereto.
  • the emission dopants include PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium). ), a phosphorescent material such as octaethylporphyrin platinum (PtOEP), or a fluorescent material such as Alq 3 (tris(8-hydroxyquinolino)aluminum), but is not limited thereto.
  • a phosphor such as Ir(ppy) 3 (fac tris(2-phenylpyridine)iridium) or a fluorescent material such as Alq3 (tris(8-hydroxyquinolino)aluminum) may be used as the emission dopant.
  • a fluorescent material such as Alq3 (tris(8-hydroxyquinolino)aluminum)
  • Alq3 tris(8-hydroxyquinolino)aluminum
  • the light emitting dopant is a phosphorescent material such as (4,6-F2ppy) 2 Irpic, spiro-DPVBi, spiro-6P, distillbenzene (DSB), distrylarylene (DSA),
  • a fluorescent material such as a PFO-based polymer or a PPV-based polymer may be used, but is not limited thereto.
  • a hole blocking layer may be provided between the electron transport layer and the light emitting layer, and the above-described compound or a material known in the art may be used for the hole blocking layer.
  • the electron transport layer may serve to facilitate transport of electrons.
  • the electron transport material a material capable of receiving electrons from the cathode and transferring them to the light emitting layer, and a material having high mobility for electrons is suitable. Specific examples include Al complex of 8-hydroxyquinoline; Complexes containing Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
  • the thickness of the electron transport layer may be 1 to 50 nm.
  • the thickness of the electron transport layer is 1 nm or more, there is an advantage of preventing deterioration of the electron transport characteristics, and if the thickness of the electron transport layer is 50 nm or less, the thickness of the electron transport layer is too thick to prevent an increase in the driving voltage to improve the movement of electrons. There is an advantage that can be.
  • the electron injection layer may serve to facilitate injection of electrons.
  • the electron injection material has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect for the light emitting layer or the light emitting material, prevents the movement of excitons generated in the light emitting layer to the hole injection layer, and , A compound having excellent thin film forming ability is preferred.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, and their derivatives, metals Complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.
  • the metal complex compound examples include lithium 8-hydroxyquinolinato, 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-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc. It is not limited to this.
  • the organic light emitting device may further include at least one hole blocking layer in addition to the hole blocking layer.
  • the hole blocking layer is a layer that prevents holes from reaching the cathode, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, etc., 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.
  • a glass substrate coated with a thin film of ITO (indium tin oxide) having a thickness of 1,000 ⁇ was put in distilled water dissolved in a detergent and washed with ultrasonic waves.
  • ITO indium tin oxide
  • a product made by Fischer Co. was used as a detergent, and distilled water secondarily filtered with a filter manufactured by Millipore Co. was used as distilled water.
  • ultrasonic cleaning 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 compound [HI-1] and the following compound [HI-2] were thermally vacuum deposited to a thickness of 100 ⁇ in a ratio of 98:2 (molar ratio) to form a hole injection layer.
  • [BH-1] and [BD-1] were vacuum-deposited at a weight ratio of 40:1 with a film thickness of 200 ⁇ to form a light emitting layer.
  • a hole blocking layer was formed by vacuum depositing the following compound [HB-1] with a film thickness of 50 ⁇ on the emission layer.
  • the compound [ET-1] and the following compound LiQ were vacuum-deposited at a weight ratio of 1:1 on the hole blocking layer to form an electron injection and transport layer with a thickness of 300 ⁇ .
  • Lithium fluoride (LiF) in a thickness of 12 ⁇ and aluminum in a thickness of 2,000 ⁇ were sequentially deposited on the electron injection and transport layer to form a negative electrode.
  • the deposition rate of the organic material was maintained at 0.4 ⁇ 0.7 ⁇ /sec
  • the deposition rate of lithium fluoride at the cathode was 0.3 ⁇ /sec
  • the deposition rate of aluminum was 2 ⁇ /sec
  • the vacuum degree during deposition was 2 ⁇ 10 ⁇ Maintaining 7 ⁇ 5 ⁇ 10 -6 torr, an organic light emitting device was manufactured.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that the compounds shown in Table 1 below were used instead of the compounds [EB-1] and [HB-1] of Comparative Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that the compounds shown in Table 1 below were used instead of the compounds [EB-1] and [HB-1] of Comparative Example 1.
  • T95 refers to the time it takes for the luminance to decrease from the initial luminance (1600 nit) to 95%.
  • the organic light emitting devices of Experimental Examples 1-1 to 1-12 basically exhibit characteristics of low voltage, high efficiency, and long life.
  • the compounds of Formula 1 have high efficiency
  • the compounds of Formula 2 It has the characteristics of long life.
  • the devices of Experimental Examples 1-1 to 1-12 showed a result that the luminous efficiency was increased by up to about 25% and the life was increased by up to about 150% compared to the comparative example.

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Abstract

La présente invention concerne un dispositif électroluminescent organique comprenant un composé représenté par la formule chimique 1 et un composé représenté par la formule chimique 2.
PCT/KR2020/010782 2019-08-14 2020-08-13 Dispositif électroluminescent organique Ceased WO2021029709A1 (fr)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113461672A (zh) * 2021-05-13 2021-10-01 上海和辉光电股份有限公司 一种多环芳烃类化合物及其应用
CN116761794A (zh) * 2021-08-23 2023-09-15 株式会社Lg化学 化合物及包含其的有机发光器件
WO2024122799A1 (fr) * 2022-12-09 2024-06-13 주식회사 엘지화학 Composé et élément électroluminescent organique le comprenant

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20180134160A (ko) * 2017-06-08 2018-12-18 주식회사 엘지화학 유기 발광 소자
KR20180137315A (ko) * 2017-06-16 2018-12-27 머티어리얼사이언스 주식회사 유기 전계 발광 소자
CN109748909A (zh) * 2017-11-02 2019-05-14 江苏三月光电科技有限公司 一种含螺氧杂蒽芴和含氮六元杂环的化合物、其制备方法及其在有机电致发光器件中的应用
CN109796442A (zh) * 2019-01-04 2019-05-24 南京邮电大学 一种螺芴氧杂蒽型电子传输材料及其制备方法和应用
KR20190088029A (ko) * 2018-01-17 2019-07-25 주식회사 엘지화학 유기 발광 소자

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004339136A (ja) 2003-05-15 2004-12-02 Idemitsu Kosan Co Ltd スピロ結合含有化合物、発光性塗膜形成用材料及びそれを用いた有機エレクトロルミネッセンス素子
DE10357044A1 (de) * 2003-12-04 2005-07-14 Novaled Gmbh Verfahren zur Dotierung von organischen Halbleitern mit Chinondiiminderivaten
CN101171224A (zh) * 2005-05-09 2008-04-30 出光兴产株式会社 新型有机电致发光材料、使用该材料的有机电致发光元件及有机电致发光用薄膜用形成溶液
CN115557879B (zh) * 2015-09-24 2024-02-20 株式会社Lg化学 化合物和包含其的有机电子器件
KR101781739B1 (ko) * 2015-10-07 2017-09-25 주식회사 엘지화학 신규 화합물 및 이를 포함하는 유기 발광 소자
KR101921377B1 (ko) * 2015-12-15 2018-11-22 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
KR20180080686A (ko) * 2017-01-04 2018-07-12 주식회사 엘지화학 유기 발광 소자

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20180134160A (ko) * 2017-06-08 2018-12-18 주식회사 엘지화학 유기 발광 소자
KR20180137315A (ko) * 2017-06-16 2018-12-27 머티어리얼사이언스 주식회사 유기 전계 발광 소자
CN109748909A (zh) * 2017-11-02 2019-05-14 江苏三月光电科技有限公司 一种含螺氧杂蒽芴和含氮六元杂环的化合物、其制备方法及其在有机电致发光器件中的应用
KR20190088029A (ko) * 2018-01-17 2019-07-25 주식회사 엘지화학 유기 발광 소자
CN109796442A (zh) * 2019-01-04 2019-05-24 南京邮电大学 一种螺芴氧杂蒽型电子传输材料及其制备方法和应用

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113461672A (zh) * 2021-05-13 2021-10-01 上海和辉光电股份有限公司 一种多环芳烃类化合物及其应用
CN116761794A (zh) * 2021-08-23 2023-09-15 株式会社Lg化学 化合物及包含其的有机发光器件
WO2024122799A1 (fr) * 2022-12-09 2024-06-13 주식회사 엘지화학 Composé et élément électroluminescent organique le comprenant

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