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WO2019083327A2 - Dispositif électroluminescent organique utilisant un composé hétérocyclique - Google Patents

Dispositif électroluminescent organique utilisant un composé hétérocyclique

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Publication number
WO2019083327A2
WO2019083327A2 PCT/KR2018/012845 KR2018012845W WO2019083327A2 WO 2019083327 A2 WO2019083327 A2 WO 2019083327A2 KR 2018012845 W KR2018012845 W KR 2018012845W WO 2019083327 A2 WO2019083327 A2 WO 2019083327A2
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unsubstituted
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WO2019083327A3 (fr
Inventor
김민준
김공겸
권혁준
차용범
이민우
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LG Chem Ltd
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LG Chem Ltd
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Priority to CN201880053589.8A priority Critical patent/CN111052428B/zh
Publication of WO2019083327A2 publication Critical patent/WO2019083327A2/fr
Publication of WO2019083327A3 publication Critical patent/WO2019083327A3/fr
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to an organic light emitting device comprising a compound represented by the formula (1) and a compound represented by the formula (2).
  • the organic light emitting device has a structure in which two electrodes and an organic layer are disposed between the two electrodes. When a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from the two electrodes couple to each other in the organic layer to form a pair, and then the light is emitted while being extinct.
  • the organic material layer may be composed of a single layer or a multilayer, if necessary.
  • the material of the organic material layer may have a light emitting function as required.
  • a compound which can form the light emitting layer by itself or a compound which can serve as a host or dopant of the host-dopant light emitting layer may be used.
  • a compound capable of performing functions such as hole injection, hole transport, hole control, electron control, electron transport, and electron injection may be used.
  • the present invention includes a compound represented by the general formula (1) in a light emitting layer and a compound represented by the general formula (2) in an organic compound layer disposed between the light emitting layer and the anode to have a low driving voltage, high light emitting efficiency, And to provide a good organic light emitting device.
  • One embodiment of the present invention relates to a positive electrode comprising: a positive electrode; cathode; A light emitting layer provided between the anode and the cathode; And an organic layer disposed between the anode and the light emitting layer,
  • the light emitting layer comprises a compound represented by the following general formula (1)
  • the organic layer provided between the anode and the light emitting layer comprises a compound represented by the following general formula (2).
  • L1 is a direct bond; Or a substituted or unsubstituted arylene group,
  • Ar1 is a substituted or unsubstituted heteroaryl group
  • R1 to R4 are the same or different from each other, and each independently hydrogen; Or deuterium, or may combine with adjacent groups to form a ring substituted or unsubstituted with deuterium,
  • R5 to R10 are the same as or different from each other, and each independently hydrogen or deuterium
  • L2 is a direct bond; Or a substituted or unsubstituted arylene group,
  • Ar2 is hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • R17 and R18 are the same or different and each independently represents a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or is bonded to each other to form a substituted or unsubstituted ring,
  • R19 and R20 are the same or different and each independently represents a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or is bonded to each other to form a substituted or unsubstituted ring,
  • S1 and S2 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; An alkyl group; A cycloalkyl group; An alkoxy group; An alkylaryl group; An aryl group; A heteroaryl group; An alkylamine group; An aralkylamine group; A heteroarylamine group; An arylamine group; Or an arylheteroarylamine group,
  • a is an integer of 0 to 7, and when a is 2 or more, S1 is the same or different,
  • b is an integer of 0 to 7, and when b is 2 or more, S2 is the same or different.
  • the light emitting layer includes the compound represented by Formula 1
  • the organic compound layer provided between the anode and the light emitting layer includes the compound represented by Formula 2, thereby lowering the driving voltage of the device, , And the efficiency can be improved.
  • FIG. 1 shows an example of an organic light-emitting device made up of a substrate 1, an anode 2, an organic material layer 3, a light-emitting layer 8 and a cathode 4.
  • FIG. 2 is a plan view of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a hole control layer 7, a light emitting layer 8, an electron control layer 9, , An electron injection layer (11), and a cathode (4).
  • FIG. 3 is a cross-sectional view showing a structure of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a hole control layer 7, a light emitting layer 8, an electron control layer 9, 12) and a cathode (4).
  • substituted or unsubstituted A halogen group; A nitrile group; An alkyl group; A cycloalkyl group; An alkoxy group; An alkylaryl group; An aryl group; A heteroaryl group; An alkylamine group; An aralkylamine group; A heteroarylamine group; An arylamine group; And an arylheteroarylamine group, or a substituted or unsubstituted group substituted with at least two of the above substituents.
  • the group in which the two substituents are connected is an aryl group or an aryl group substituted with a heteroaryl group; A heteroaryl group substituted with an aryl group or a heteroaryl group, and the like.
  • the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.
  • Examples of the group to which the three substituents are connected include an aryl group substituted with a heteroaryl group substituted with an aryl group, an aryl group substituted with an aryl group substituted with a heteroaryl group, a heteroaryl group substituted with an aryl group substituted with a heteroaryl group, and the like .
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 30 carbon atoms. According to another embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms.
  • alkyl group examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec- , n-hexyl, 1-methylpentyl, 2-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, Octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, Hexyl, 5-methylhexyl, and the like, but are not limited thereto.
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 10 carbon atoms. Specific examples thereof include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 3-methylcyclohexyl, cycloheptyl, cyclooctyl and the like.
  • the alkoxy group is not particularly limited, but preferably has 1 to 40 carbon atoms. According to one embodiment, the number of carbon atoms in the alkoxy group is from 1 to 10. According to another embodiment, the number of carbon atoms of the alkoxy group is from 1 to 6. Specific examples of the alkoxy group include, but are not limited to, a methoxy group, an ethoxy group, a propoxy group, an isobutyloxy group, a sec-butyloxy group, a pentyloxy group, an isoamyloxy group and a hexyloxy group.
  • an aryl group means a hydrocarbon ring having a fully or partially unsaturated directionality.
  • the number of carbon atoms of 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 one embodiment, the aryl group has 6 to 45 carbon atoms. According to one embodiment, the aryl group has 6 to 35 carbon atoms.
  • the aryl group may be a phenyl group, a biphenyl group, a terphenyl group or the like as the monocyclic aryl group, but is not limited thereto.
  • the polycyclic aryl group may be, for example, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, perylenyl, klycenyl, fluorenyl, no.
  • the substituted fluorenyl group when the fluorenyl group can be substituted, includes all of the compounds in which the substituents on the pentagonal ring of the fluorene are spiro bonded to each other to form an aromatic hydrocarbon ring.
  • Such substituted fluorenyl groups include 9,9'-spirobifluorene, spiro [cyclopentane-1,9'-fluorene], spiro [benzo [c] fluorene-7,9-fluorene] But is not limited thereto.
  • a heteroaryl group refers to a monocyclic or polycyclic, containing at least one of N, O, and S as heteroatoms and being totally or partially unsaturated.
  • the number of carbon atoms of the heteroaryl group is not particularly limited, but is preferably 2 to 60 carbon atoms. According to one embodiment, the heteroaryl group has 2 to 45 carbon atoms. According to another embodiment, the heteroaryl group has 2 to 35 carbon atoms.
  • heteroaryl group examples include a thiophenyl group, a furanyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a triazolyl group, a pyridinyl group, a bipyridinyl group, a pyrimidinyl group, A thienyl group, a thienyl group, a thienyl group, a thiazolyl group, a thiazolyl group, a triazolyl group, an acridinyl group, a carbolinyl group, an acenaphthoquinoxalinyl group, an indenopyrimidinyl group, an indenoquinazolinyl group, an indenoisoquinolinyl group, A pyridazinyl group, a pyridazinyl group, a
  • the heteroaryl group includes an aliphatic heteroaryl group and an aromatic heteroaryl group.
  • the arylamine group means a group in which the nitrogen atom of the amine is substituted with an aryl group.
  • the arylamine group include a substituted or unsubstituted monoarylamine group; Or a substituted or unsubstituted diarylamine group.
  • the aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group.
  • the arylamine group containing two or more aryl groups is a monocyclic aryl group; Or a polycyclic aryl group, or may contain both a monocyclic aryl group and a polycyclic aryl group at the same time.
  • arylamine group examples include phenylamine, naphthylamine, biphenylamine, anthracenylamine, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group and the like, no.
  • the heteroarylamine group means a group in which the nitrogen atom of the amine is substituted with a heteroaryl group.
  • Heteroarylamine groups include, for example, substituted or unsubstituted monoheteroarylamine groups; Or a substituted or unsubstituted diheteroarylamine group.
  • the heteroaryl group in the heteroarylamine group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group.
  • the heteroarylamine group containing two or more heteroaryl groups is a monocyclic heteroaryl group; Or a polycyclic heteroaryl group, or may contain both a monocyclic heteroaryl group and a polycyclic heteroaryl group at the same time.
  • the arylheteroarylamine group means an amine group substituted with an aryl group and a heteroaryl group.
  • the aralkylamine group means an aryl group and an amine group substituted with an alkyl group.
  • alkyl group in the aralkylamine group and the alkylaryl group may be described with respect to the alkyl group described above.
  • the aryl group in the arylheteroarylamine group, the aralkylamine group, and the arylamine group may be the same as the aryl group described above.
  • heteroaryl group in the arylheteroarylamine group can be applied to the description of the above-mentioned heteroaryl group.
  • alkyl groups, cycloalkyl groups, aryl groups and heteroaryl groups are applicable, except that the alkylene group, cycloalkylene group, arylene group and heteroarylene group are each a divalent group.
  • One embodiment of the present disclosure relates to a battery pack comprising: a positive electrode; cathode; A light emitting layer provided between the anode and the cathode; And an organic layer disposed between the anode and the light emitting layer, wherein the light emitting layer includes a compound represented by the following Formula 1, and the organic layer disposed between the anode and the light emitting layer is represented by Formula 2 And a compound represented by the following general formula (1).
  • L1 is a direct bond; Or a substituted or unsubstituted arylene group,
  • Ar1 is a substituted or unsubstituted heteroaryl group
  • R1 to R4 are the same or different from each other, and each independently hydrogen; Or deuterium, or may combine with adjacent groups to form a ring substituted or unsubstituted with deuterium,
  • R5 to R10 are the same as or different from each other, and each independently hydrogen or deuterium
  • L2 is a direct bond; Or a substituted or unsubstituted arylene group,
  • Ar2 is hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • R17 and R18 are the same or different and each independently represents a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or is bonded to each other to form a substituted or unsubstituted ring,
  • R19 and R20 are the same or different and each independently represents a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or is bonded to each other to form a substituted or unsubstituted ring,
  • S1 and S2 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; An alkyl group; A cycloalkyl group; An alkoxy group; An alkylaryl group; An aryl group; A heteroaryl group; An alkylamine group; An aralkylamine group; A heteroarylamine group; An arylamine group; Or an arylheteroarylamine group,
  • a is an integer of 0 to 7, and when a is 2 or more, S1 is the same or different,
  • b is an integer of 0 to 7, and when b is 2 or more, S2 is the same or different.
  • adjacent group means a group in which a substituent is substituted on an atom directly connected to a substituted atom; May refer to the substituent located closest to the substituent stereostatically.
  • R 1 and R 2 in formula (1) of the present invention are each adjacent groups, but R & And R4 and L1 do not correspond to adjacent groups.
  • the meaning of forming a substituted or unsubstituted ring by bonding to adjacent groups means that the adjacent groups are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic hydrocarbon ring, Substituted aliphatic heterocycle, a substituted or unsubstituted aromatic heterocycle, or a condensed ring thereof.
  • R 1 to R 4 combine with adjacent groups to form a ring. In one embodiment, R 1 to R 4 combine with adjacent groups to form a substituted or unsubstituted aromatic hydrocarbon ring.
  • the substituted or unsubstituted ring formed by combining R1 to R4 with adjacent groups is an aromatic hydrocarbon ring substituted or unsubstituted with deuterium.
  • the substituted or unsubstituted ring formed by combining R1 to R4 with adjacent groups is a benzene ring substituted or unsubstituted with deuterium.
  • R1 to R4 are bonded to adjacent groups to form a ring
  • R1 and R2 may be combined to form a ring
  • R2 and R3 may be combined to form a ring
  • R3 And R4 are combined to form a ring.
  • R 1 and R 2 combine with each other to form a benzene ring substituted or unsubstituted with deuterium. In another embodiment, R 1 and R 2 combine with each other to form a benzene ring.
  • R 2 and R 3 are bonded to each other to form a benzene ring substituted or unsubstituted with deuterium.
  • R < 2 > and R < 3 > are bonded to each other to form a benzene ring.
  • R 3 and R 4 combine with each other to form a benzene ring substituted or unsubstituted with deuterium. In another embodiment, R 3 and R 4 combine with each other to form a benzene ring.
  • R1 to R10 are the same as or different from each other, and each independently hydrogen or deuterium.
  • each of R1 to R10 is hydrogen.
  • each of R5 to R10 is hydrogen.
  • the group which is not bonded to the adjacent group of R1 to R4 and does not condense the ring is hydrogen.
  • L1 is a direct bond; Or a substituted or unsubstituted arylene group.
  • L1 is a direct bond; Or a substituted or unsubstituted arylene group having 6 to 45 carbon atoms.
  • L1 is a direct bond; Or a substituted or unsubstituted arylene group having 6 to 35 carbon atoms.
  • L1 is a direct bond; Or a substituted or unsubstituted arylene group having 6 to 25 carbon atoms.
  • L1 is a direct bond; Or an arylene group substituted or unsubstituted with an alkyl group, an aryl group or a heteroaryl group.
  • L1 is a direct bond; A substituted or unsubstituted phenylene group; Or a substituted or unsubstituted naphthylene group.
  • L1 is a direct bond; A 1,3-phenylene group; 1,4-phenylene group; 1,3-naphthylene group; 1,4-naphthylene group; Or a 1,5-naphthylene group.
  • Ar1 is a substituted or unsubstituted heteroaryl group.
  • Ar1 is a substituted or unsubstituted heteroaryl group
  • R60 is a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • R60 is a C1-C10 alkyl group; A C6-C30 aryl group substituted or unsubstituted with an alkyl group of C1-C10 or an aryl group of C6-C30; Or a C2-C30 heteroaryl group substituted or unsubstituted with an aryl group of C6-C30.
  • R60 is a C1-C6 alkyl group; A C6-C25 aryl group substituted or unsubstituted with a C1-C6 alkyl group or a C6-C18 aryl group; Or a C2-C25 heteroaryl group substituted or unsubstituted with an aryl group of C6-C18.
  • R60 is a methyl group; A phenyl group; Naphthyl group; A biphenyl group; A dimethylfluorenyl group; A phenanthrenyl group; A carbazolyl group substituted with a phenyl group; A dibenzofuranyl group; Or a dibenzothiophenyl group.
  • Ar1 is a substituted or unsubstituted heteroaryl group containing at least 2 N atoms.
  • Ar1 is a substituted or unsubstituted heteroaryl group containing a 6-membered aromatic ring containing 2 or more N.
  • Ar1 is represented by the following formula (4).
  • X1 to X5 are the same or different from each other and each independently N or CR,
  • R is hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or adjacent R's may be bonded to each other to form a substituted or unsubstituted ring,
  • At least two of X1 to X5 are N,
  • Two or more R's are the same or different from each other.
  • two or three of X1 to X5 are N.
  • R is selected from the group consisting of hydrogen; An aryl group substituted or unsubstituted with an alkyl group or an aryl group; Or a heteroaryl group substituted or unsubstituted with an aryl group, or adjacent Rs may be bonded to each other to form a ring substituted or unsubstituted with R50; An alkyl group; An aryl group substituted or unsubstituted with an alkyl group or an aryl group; Or a heteroaryl group substituted or unsubstituted with an aryl group.
  • R50 is a C1-C10 alkyl group; A C6-C30 aryl group substituted or unsubstituted with an alkyl group of C1-C10 or an aryl group of C6-C30; Or a C2-C30 heteroaryl group substituted or unsubstituted with an aryl group of C6-C30.
  • R50 is a C1-C6 alkyl group; A C6-C25 aryl group substituted or unsubstituted with a C1-C6 alkyl group or a C6-C18 aryl group; Or a C2-C25 heteroaryl group substituted or unsubstituted with an aryl group of C6-C18.
  • R50 is an alkyl group.
  • R50 is selected from the group consisting of hydrogen; Or a methyl group.
  • X1 to X5 are CR, two are N, and the remaining one is CR ', and two R's are bonded to each other to form a substituted or unsubstituted ring
  • X1 to X5 are the same or different from each other and each independently N or CR ', at least two of X1, X3 and X5 are N, and R' is hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, and when R 'is 2 or more, R' is the same or different.
  • X1 to X5 are CR, two are N, and the remaining one is CR ', and two R's are bonded to each other to form a substituted or unsubstituted ring
  • X1, X3 and X5 are each independently N or CH, at least two of X1, X3 and X5 are N, X2 to X4 are each independently CR 'and R' is hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, and when R 'is 2, R' are the same or different.
  • R ' is hydrogen; An aryl group substituted or unsubstituted with an alkyl group or an aryl group; Or a heteroaryl group substituted or unsubstituted with an aryl group.
  • R ' is an aryl group substituted or unsubstituted with an alkyl group or an aryl group; Or a heteroaryl group substituted or unsubstituted with an aryl group.
  • R ' is hydrogen; A phenyl group; Naphthyl group; A biphenyl group; A dimethylfluorenyl group; A phenanthrenyl group; A carbazolyl group substituted with a phenyl group; A dibenzofuranyl group; Or a dibenzothiophenyl group.
  • the substituted or unsubstituted ring formed by bonding the two Rs to each other is selected from the group consisting of benzene; naphthalene; 1,1-dimethyl-2,3-dihydro-1H-indene; Benzothiophene; Or benzofuran.
  • Ar1 is represented by any one of the following formulas (4-1) to (4-4).
  • A1 and A2 are the same or different and are each independently a substituted or unsubstituted ring
  • G1 to G7 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • A1 and A2 are the same or different and are each independently a ring substituted or unsubstituted with an alkyl group.
  • a 1 and A 2 are the same or different and are each independently a substituted or unsubstituted monocyclic or bicyclic ring.
  • A1 and A2 are the same or different from each other and each independently represent benzene; naphthalene; 1,1-dimethyl-2,3-dihydro-1H-indene; Benzothiophene; Or benzofuran.
  • G1 to G7 are the same or different from each other, and each independently hydrogen; An aryl group substituted or unsubstituted with an alkyl group or an aryl group; Or a heteroaryl group substituted or unsubstituted with an aryl group.
  • G1 to G7 are the same or different from each other, and each independently hydrogen; A phenyl group; Naphthyl group; A biphenyl group; A dimethylfluorenyl group; A phenanthrenyl group; A carbazolyl group substituted with a phenyl group; A dibenzofuranyl group; Or a dibenzothiophenyl group.
  • G1 and G2 are the same or different and each independently represents an aryl group substituted or unsubstituted with an alkyl group or an aryl group; Or a heteroaryl group substituted or unsubstituted with an aryl group.
  • At least one of G3 and G4 is an aryl group substituted or unsubstituted with an alkyl group or an aryl group; Or a heteroaryl group substituted or unsubstituted with an aryl group.
  • G3 and G4 are the same or different and each independently represents an aryl group substituted or unsubstituted with an alkyl group or an aryl group; Or a heteroaryl group substituted or unsubstituted with an aryl group.
  • At least one of G5 to G7 is an aryl group substituted or unsubstituted with an alkyl group or an aryl group; Or a heteroaryl group substituted or unsubstituted with an aryl group.
  • At least two of G5 to G7 are an aryl group substituted or unsubstituted with an alkyl group or an aryl group; Or a heteroaryl group substituted or unsubstituted with an aryl group.
  • Ar1 is any one selected from the following groups.
  • R21 to R33 are the same or different and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • a21 is an integer of 0 to 5, and when a21 is 2 or more, R21 is the same or different,
  • a22 is an integer of 0 to 5, and when a22 is 2 or more, R22 is the same or different,
  • a23 is an integer of 0 to 2, and when a23 is 2, R23 is the same or different,
  • a24 is an integer of 0 to 3, and when a24 is 2 or more, R24 is the same or different,
  • a25 is an integer of 0 to 7, and when a25 is 2 or more, R25 is the same or different,
  • a26 is an integer of 0 to 7, and when a26 is 2 or more, R26 is the same or different,
  • a27 is an integer of 0 to 7, and when a27 is 2 or more, R27 is the same or different,
  • a28 is an integer of 0 to 5, and when a28 is 2 or more, R28 is the same or different,
  • a29 is an integer of 0 to 5, and when a29 is 2 or more, R29 is the same or different,
  • a30 is an integer of 0 to 5, and when a30 is 2 or more, R30 is the same or different,
  • a31 is an integer of 0 to 5, and when a31 is 2 or more, R31 is the same or different,
  • a32 is an integer of 0 to 5, and when a32 is 2 or more, R32 is the same or different,
  • a33 is an integer of 0 to 5, and when a33 is 2 or more, R33 is the same or different.
  • R21 to R33 are the same or different and each independently represents an aryl group substituted or unsubstituted with an alkyl group or an aryl group; Or a heteroaryl group substituted or unsubstituted with an aryl group.
  • R21 to R33 are the same or different and each independently represents a C6-C30 aryl group substituted or unsubstituted with a C1-C10 alkyl group or a C6-C30 aryl group; Or a C2-C30 heteroaryl group substituted or unsubstituted with an aryl group of C6-C30.
  • R21 to R33 are the same or different and each independently represents a C6-C25 aryl group substituted or unsubstituted with a C1-C6 alkyl group or a C6-C18 aryl group; Or a C2-C25 heteroaryl group substituted or unsubstituted with an aryl group of C6-C18.
  • R21 to R33 are the same or different from each other and are each independently a phenyl group; Naphthyl group; A biphenyl group; A dimethylfluorenyl group; A phenanthrenyl group; A carbazolyl group substituted with a phenyl group; A dibenzofuranyl group; Or a dibenzothiophenyl group.
  • a21, a22 and a25 to a33 are each independently 0 or 1.
  • a24 is an integer of 0 to 2.
  • Ar1 is any one selected from the following groups.
  • R21 to R33 are the same or different and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • a23 is an integer of 0 to 2, and when a23 is 2, R23 is the same or different,
  • a24 is an integer of 0 to 3, and when a24 is 2 or more, R24 is the same or different,
  • b21, b22 and b25 to b33 are each independently 0 or 1.
  • a23 is 1 or 2.
  • a24 is 1 or 2.
  • b21, b22, and b25 to b33 are 1, respectively.
  • the substituted or unsubstituted ring formed by combining R17 and R18 with each other is a substituted or unsubstituted fluorene ring.
  • the groups R17 and R18 are each a single bond portion of a pentagonal ring of fluorene.
  • the substituted or unsubstituted ring formed by combining R19 and R20 is a substituted or unsubstituted fluorene ring.
  • the groups of R19 and R20 are each a single bond portion of a pentagonal ring of fluorene.
  • R17 and R18 are the same or different from each other and are each independently a C1-C10 alkyl group; Or an aryl group of C6-C25, or combine with each other to form a C6-C30 ring.
  • R17 and R18 are the same or different from each other and are each independently a C1-C6 alkyl group; Or an aryl group of C6-C18, or combine with each other to form a C6-C20 ring.
  • R19 and R20 are the same or different from each other and are each independently a C1-C10 alkyl group; Or an aryl group of C6-C25, or combine with each other to form a C6-C30 ring.
  • R19 and R20 are the same or different and are each independently a C1-C6 alkyl group; Or an aryl group of C6-C18, or combine with each other to form a C6-C20 ring.
  • R17 and R18 are the same or different from each other and are each independently a methyl group; Or a phenyl group, or combine with each other to form a fluorene ring.
  • R19 and R20 are the same or different from each other, and each independently represents a methyl group; Or a phenyl group, or combine with each other to form a fluorene ring.
  • L2 is a substituted or unsubstituted arylene group.
  • L2 is an arylene group substituted or unsubstituted with an aryl group or a heteroaryl group.
  • L2 is an arylene group substituted or unsubstituted with at least one substituent selected from the group consisting of a phenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group.
  • L2 is a substituted or unsubstituted phenylene group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted fluorenylene group; A substituted or unsubstituted phenanthrenylene group; A substituted or unsubstituted biphenylene group; Or a substituted or unsubstituted triphenylene group.
  • L2 represents a phenylene group; Naphthylene group; A fluorenylene group; Phenanthrenylene group; Biphenyllylene groups; Or a triphenylenylene group.
  • Ar2 is hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • Ar2 is hydrogen; A substituted or unsubstituted C1-C15 alkyl group; A substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted C2-C30 heteroaryl group.
  • Ar2 is hydrogen; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted C6-C25 aryl group; Or a substituted or unsubstituted C2-C25 heteroaryl group.
  • Ar2 is hydrogen; A substituted or unsubstituted C1-C6 alkyl group; A substituted or unsubstituted C6-C18 aryl group; Or a substituted or unsubstituted C2-C12 heteroaryl group.
  • Ar2 is selected from the group consisting of hydrogen; An alkyl group; An aryl group substituted or unsubstituted with an alkyl group, an aryl group or a heteroaryl group; Or a heteroaryl group substituted or unsubstituted with an alkyl group, an aryl group or a heteroaryl group.
  • Ar2 is hydrogen; An alkyl group; An aryl group substituted or unsubstituted with an aryl group; Or a heteroaryl group substituted or unsubstituted with an aryl group.
  • Ar2 is hydrogen; An alkyl group; An aryl group substituted or unsubstituted with a phenyl group; Or a heteroaryl group substituted or unsubstituted with a phenyl group.
  • the alkyl group when Ar2 is an alkyl group, the alkyl group may be a methyl group.
  • the substituted or unsubstituted aryl group may be 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 fluorenyl group; A substituted or unsubstituted phenanthrenyl group; Or a substituted or unsubstituted triphenylenyl group.
  • the substituted or unsubstituted aryl group is preferably a phenyl group; A biphenyl group; A terphenyl group; Naphthyl group; A dimethylfluorenyl group; A phenanthrenyl group; Or a triphenylenyl group.
  • the substituted or unsubstituted heteroaryl group may be substituted or unsubstituted carbazolyl group; A substituted or unsubstituted dibenzofuranyl group; Or a substituted or unsubstituted dibenzothiophenyl group.
  • the substituted or unsubstituted heteroaryl group may be substituted with a phenyl group; A dibenzofuranyl group; Or a dibenzothiophenyl group.
  • S1 and S2 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; An alkyl group; A cycloalkyl group; An alkoxy group; An alkylaryl group; An aryl group; A heteroaryl group; An alkylamine group; An aralkylamine group; A heteroarylamine group; An arylamine group; Or an arylheteroarylamine group.
  • a is zero.
  • b is zero.
  • the formula (1) is represented by the following formula (3).
  • R11 and R12 are each deuterium
  • c is an integer of 0 to 4
  • d is an integer of 0 to 2.
  • the formula (1) is represented by any one of the following formulas (3A) to (3C).
  • R1 to R4 and R13 to R16 are the same as or different from each other, and each independently hydrogen or deuterium.
  • the compound represented by Formula 1 is any one selected from the following compounds.
  • the compound represented by Formula 2 is any one selected from the following compounds.
  • the organic material layer of the organic light emitting device of the present invention has a multilayer structure in which two or more organic material layers are laminated.
  • the organic light emitting device of the present invention may have a structure including a hole injecting layer, a hole transporting layer, a hole controlling layer, a light emitting layer, an electron controlling layer, an electron transporting layer, and an electron injecting layer as organic layers.
  • the structure of the organic light emitting device is not limited thereto, and may include fewer or larger numbers of organic layers.
  • the light emitting layer includes a compound represented by Formula 1 as a host.
  • the light emitting layer further includes a dopant.
  • the dopant may be a phosphorescent dopant or a fluorescent dopant.
  • the phosphorescent dopants are those conventionally used in the art and include tris (2-phenylpyridinato-N, C2) ruthenium, bis (2-phenylpyridinato-N, C2) palladium, bis (2-phenylpyridinato-N, C2) rhenium, octaethylplatinum porphyrin, octaphenylplatinum porphyrin, octaethyl (4,6-difluorophenyl) -pyridinate-N, C2 '] picolinate (Firpic), tris (2-phenylpyridinato- N, C2) iridium (Ir (ppy) 3), fac- tris (2-phenylpyridine) iridium (iii) (fac-Ir ( ppy) 3), bis (2-phenylpyridinato -N Deen Sat, C2) Iridium (acetylacetonate) (
  • fluorescent dopant examples include Alq 3 (tris (8-hydroxyquinolino) aluminum), spiro-DPVBi, spiro-6P, distyrylbenzene (DSB), distyrylarylene (DSA), PFO- Bis (diphenylamine) pyrene, tetrakis (t-butyl) perylene, p-bis (pN, N-diphenyl-aminostyryl) Pheny1 cyclopentadiene, and the like, but the present invention is not limited thereto.
  • the dopant may be any one selected from the following materials.
  • the organic material layer may further include another light emitting layer not containing the compound represented by Formula 1.
  • the organic compound layer provided between the anode and the light emitting layer includes the compound represented by Formula 2.
  • the organic material layer provided between the anode and the light emitting layer includes a hole transporting and injecting layer, a hole transporting layer, a hole injecting layer, or a hole controlling layer.
  • the organic layer provided between the anode and the light emitting layer includes a hole controlling layer, and the hole controlling layer includes a compound represented by the above formula (2).
  • the hole-adjusting layer is in contact with the light-emitting layer.
  • the organic light emitting diode further includes an organic layer disposed between the cathode and the organic layer.
  • the organic material layer provided between the cathode and the organic material layer includes an electron transporting layer, an electron injecting layer, a layer (hereinafter referred to as an electron transporting and injecting layer) Or an electron control layer.
  • the organic light emitting device may be a normal type organic light emitting device in which an anode, at least one organic layer, 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, at least one organic material layer, and an anode are sequentially stacked on a substrate.
  • the structure of the organic light emitting device according to one embodiment of the present specification is illustrated in Figs.
  • the compound represented by Formula 1 shows an example of an organic light-emitting device made up of a substrate 1, an anode 2, an organic material layer 3, a light-emitting layer 8 and a cathode 4.
  • the compound represented by Formula 1 may be included in the light emitting layer 8
  • the compound represented by Formula 2 may be included in the organic layer 3.
  • FIG. 2 is a plan view of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a hole control layer 7, a light emitting layer 8, an electron control layer 9, , An electron injection layer (11), and a cathode (4).
  • the compound represented by Formula 1 may be included in the light emitting layer 8, and the compound represented by Formula 2 may be contained in the hole injecting layer 5, the hole transporting layer 6 or the hole controlling layer 7, .
  • FIG. 3 is a cross-sectional view showing a structure of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a hole control layer 7, a light emitting layer 8, an electron control layer 9, 12) and a cathode (4).
  • the compound represented by Formula 1 may be included in the light emitting layer 8, and the compound represented by Formula 2 may be contained in the hole injecting layer 5, the hole transporting layer 6 or the hole controlling layer 7, .
  • the structure of the organic light emitting diode according to one embodiment of the present invention is not limited to the above-described FIG. 1 to FIG. 3, and may be any one of the following structures.
  • the organic layers may be formed of the same material or different materials.
  • the organic light emitting device of the present invention can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate.
  • a metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate by physical vapor deposition (PVD) such as sputtering or e-beam evaporation Forming an anode, forming an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer and an electron transporting layer on the anode, and depositing a material usable as a cathode thereon.
  • PVD physical vapor deposition
  • an organic light emitting device may be formed by sequentially depositing an organic material layer and a cathode material from a cathode material on a substrate.
  • the manufacturing method is not limited thereto.
  • the cathode material a material having a large work function is preferably used so that hole injection can be smoothly conducted into the organic material layer.
  • 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; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline.
  • the negative electrode material is preferably a material having a small work function to facilitate electron injection into the organic material layer.
  • Specific examples of 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; Layer structure materials such as LiF / Al or LiO 2 / Al, but are not limited thereto.
  • the hole injection layer is a layer for injecting holes, which are received from the electrode, into an adjacent layer provided to the light emitting layer or the light emitting layer.
  • the hole injecting material has a hole injecting effect on the anode, an excellent hole injecting effect on the light emitting layer or the light emitting material due to its ability to transport holes, and the migration of the excitons generated in the light emitting layer to the electron injecting layer or the electron injecting material It is preferable to use a compound having excellent ability to form a thin film.
  • the highest occupied molecular orbital (HOMO) of the hole injecting material is preferably between the work function of the anode material and the HOMO of the surrounding organic layer.
  • the hole injecting material include organic materials such as metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene- Based organic materials, anthraquinone, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
  • organic materials such as metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene- Based organic materials, anthraquinone, and polyaniline and polythiophene-based conductive polymers, 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 light emission layer.
  • the hole transporting material a material capable of transporting holes from the anode or the hole injecting layer to the light emitting layer and having high mobility to holes is suitable.
  • Specific examples of the hole transporting material include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but the present invention is not limited thereto.
  • the hole-adjusting layer is a light-emitting layer that prevents exciter electrons from entering the anode and regulates the performance of the entire device by controlling the flow of holes flowing into the light-emitting layer.
  • the hole-controlling material is preferably a compound having an ability to prevent the flow of electrons from the light-emitting layer to the anode and to control the flow of holes injected into the light-emitting layer or the light-emitting material.
  • arylamine-based organic materials may be used as the hole-adjusting layer, but the present invention is not limited thereto.
  • the light emitting material is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having good quantum efficiency for fluorescence or phosphorescence.
  • the luminescent material include 8-hydroxyquinoline aluminum complex (Alq 3 ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; Benzoxazole, benzothiazole and benzimidazole compounds; Polymers of poly (p-phenylenevinylene) (PPV) series; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.
  • the light emitting layer may include a host material and a dopant material.
  • the host material is a condensed aromatic ring derivative or a heterocyclic compound.
  • Specific examples of the condensed aromatic ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds and fluoranthene compounds.
  • Examples of heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • Examples of the dopant material of the light emitting layer include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes.
  • aromatic amine derivative a condensed aromatic ring derivative having a substituted or unsubstituted arylamine group may be used, such as pyrene, anthracene, klysene, and peripherrhene having an arylamine group.
  • As the styrylamine compound a compound in which substituted or unsubstituted arylamine is substituted with at least one aryl vinyl group can be used.
  • styrylamine compound examples include, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like.
  • metal complex an iridium complex, a platinum complex, or the like can be used, but it is not limited thereto.
  • the electron control layer is a layer that blocks the flow of holes from the light emitting layer into the cathode and adjusts the performance of the entire device by controlling electrons flowing into the light emitting layer.
  • the electron control material is preferably a compound capable of preventing the inflow of holes from the light emitting layer to the cathode and controlling the electrons injected into the light emitting layer or the light emitting material.
  • As the electron control material an appropriate material may be used depending on the constitution of the organic material layer used in the device.
  • the electron control layer is disposed between the light emitting layer and the cathode, and is preferably provided directly in contact with the light emitting layer.
  • the electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emission layer.
  • the electron transporting material a material capable of transferring electrons from the cathode well into the light emitting layer, which is suitable for electrons, is suitable.
  • the electron transporting material include an Al complex of 8-hydroxyquinoline; Complexes containing Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complex, and the like, but are not limited thereto.
  • the electron transporting layer can be used with any desired cathode material as used according to the prior art.
  • the negative electrode material comprises a material having a low work function; And an aluminum layer or a silver layer may be used. Examples of the material having the low work function include cesium, barium, calcium, ytterbium, and samarium.
  • An aluminum layer or a silver layer may be formed on the layer after forming the layer with the material.
  • the electron injection layer is a layer for injecting electrons received from the electrode into the light emitting layer.
  • the electron injecting material has an ability to transport electrons, has an electron injecting effect from the cathode, an excellent electron injecting effect to the emitting layer or the light emitting material, prevents migration of the excitons produced in the emitting layer into the hole injecting layer, Further, it is preferable to use a compound having excellent ability to form a thin film.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, A complex compound and a nitrogen-containing five-membered ring derivative, but are not limited thereto.
  • Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8- hydroxyquinolinato) gallium, bis (10- Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8- quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, and the like, But is not limited thereto.
  • the organic light emitting device according to the present invention may be of a top emission type, a back emission type, or a both-side emission type, depending on the material used.
  • the compound represented by formula (1) may be prepared by reacting a known compound such as a Heck coupling reaction, a suzuki coupling reaction and a Buchwald-Hartwig amination reaction Method. ≪ / RTI > All the compounds used in the following Experimental Examples were subjected to sublimation purification after purification and device evaluation was carried out.
  • a known compound such as a Heck coupling reaction, a suzuki coupling reaction and a Buchwald-Hartwig amination reaction Method. ≪ / RTI > All the compounds used in the following Experimental Examples were subjected to sublimation purification after purification and device evaluation was carried out.
  • the compounds of formula (I) of the present invention are prepared by the known Buchwald-Hartwig amination reaction.
  • the compound represented by Formula 1 may be prepared by substituting a substituent on nitrogen of a compound containing benzocarbazole or dibenzocarbazole.
  • the benzocarbazole or dibenzocarbazole contained in Formula 1 of the present invention was prepared by the following Production Examples 1-4.
  • Naphthalene-2-amine 300g (1eq), 1- bromo-2-iodo-benzene 592.7g (1eq), sodium t- butoxide, 302g (1.5eq), Pd (OAc ) 2 4.7g (0.01eq) and janteu 12.12 g (0.01 eq) of Xantphos was dissolved in 5 L of 1.4-dioxane, refluxed and stirred. When the reaction was completed after 3 hours, the solvent was removed by decompression. The reaction mixture was then completely dissolved in ethyl acetate, washed with water, and then reduced in pressure to remove about 70% of the solvent.
  • Dibenzo [b, h] carbazole) was synthesized in the same manner as in Production Example 1 using 2,3-dibromonaphthalene instead of 1-bromo-2-iodobenzene.
  • a method of binding a substituent to nitrogen of a compound containing benzocarbazole or dibenzocarbazole is as follows.
  • the synthesis method of the formula (7) is described as an example of a method for producing the compound represented by the above formula (1).
  • the glass substrate coated with ITO (indium tin oxide) thin film with a thickness of 1,000 ⁇ was immersed in distilled water containing detergent and washed with ultrasonic waves. At this time, Fischer Co. product was used as a detergent, and distilled water, which was secondly filtered with a filter of Millipore Co., was used as distilled water.
  • the ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator.
  • the following HI-1 compound was formed to a thickness of 1150 ANGSTROM as a hole injecting layer, and the following compound A-1 was p-doped to 1.5 wt%.
  • the following HT-1 compound was vacuum deposited on the hole injection layer to form a hole transport layer having a thickness of 800 ANGSTROM.
  • the following 1-6 compounds were vacuum deposited on the hole transport layer to a thickness of 150 ⁇ to form a hole control layer.
  • the following RH-1 compound and the following Dp-7 compound were vapor deposited on the hole-transporting layer at a weight ratio of 98: 2 to form a 400 ⁇ -thick red light-emitting layer.
  • HB-1 compound was vacuum deposited on the light emitting layer to a thickness of 30 ANGSTROM to form an electron control layer. Subsequently, the following ET-1 compound and the following LiQ compound were vacuum-deposited on the electron control layer at a weight ratio of 2: 1 to form an electron injection and transport layer having a thickness of 300 ⁇ . Lithium fluoride (LiF) and aluminum having a thickness of 1,000 ⁇ were sequentially deposited on the electron injecting and transporting layer to form a cathode.
  • LiF lithium fluoride
  • aluminum having a thickness of 1,000 ⁇ were sequentially deposited on the electron injecting and transporting layer to form a cathode.
  • the deposition rate of the organic material was maintained in the range of 0.4 ⁇ / sec to 0.7 ⁇ / sec, the deposition rate of the lithium fluoride of the cathode was 0.3 ⁇ / sec and the deposition rate of the aluminum film was maintained at 2 ⁇ / sec. ⁇ 10 -7 to 5 ⁇ 10 -6 torr.
  • T 98 means the time required for the luminance to decrease from the initial luminance (5000 nits) to 98%.
  • An organic light emitting device was prepared in the same manner as in Comparative Example 1, except that the compounds shown in the following Table 1 were used instead of the compounds 1-6 and RH-1 in Experimental Example 1.
  • An organic light emitting device was fabricated in the same manner as in Comparative Example 1 except that the compound 1-81 was used in place of the compound 1-6 in the Experimental Example 1 and the compound of Table 2 was used instead of the compound RH-1.
  • An organic light emitting device was prepared in the same manner as in Comparative Example 1, except that the compounds shown in Table 3 were used instead of the compounds 1-6 and RH-1 in Experimental Example 1.

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Abstract

L'invention concerne un élément électroluminescent organique comprenant : une électrode positive; une électrode négative; une couche électroluminescente placée entre l'électrode positive et l'électrode négative; et une couche organique placée entre l'électrode positive et la couche électroluminescente, la couche électroluminescente comprenant un composé représenté par la formule chimique 1, et la couche organique placée entre la cathode et la couche électroluminescente comprend un composé représenté par la formule chimique 2.
PCT/KR2018/012845 2017-10-27 2018-10-26 Dispositif électroluminescent organique utilisant un composé hétérocyclique Ceased WO2019083327A2 (fr)

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CN110776500A (zh) * 2019-11-29 2020-02-11 烟台显华化工科技有限公司 一类有机化合物及其应用
WO2022207678A1 (fr) 2021-03-30 2022-10-06 Merck Patent Gmbh Dispositif électroluminescent organique

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CN111052428B (zh) 2023-09-29

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