WO2023200226A1 - 화합물 및 이를 포함하는 유기 발광 소자 - Google Patents

화합물 및 이를 포함하는 유기 발광 소자 Download PDF

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WO2023200226A1
WO2023200226A1 PCT/KR2023/004879 KR2023004879W WO2023200226A1 WO 2023200226 A1 WO2023200226 A1 WO 2023200226A1 KR 2023004879 W KR2023004879 W KR 2023004879W WO 2023200226 A1 WO2023200226 A1 WO 2023200226A1
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이성재
문현진
김민준
전현수
홍성길
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주식회사 엘지화학
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    • C07C2603/97—Spiro compounds containing "not free" spiro atoms containing at least one ring with less than six members containing five-membered rings

Definitions

  • This specification relates to compounds and organic light-emitting devices containing the same.
  • organic luminescence refers to a phenomenon that converts electrical energy into light energy using organic materials.
  • Organic light-emitting devices that utilize the organic light-emitting phenomenon usually have a structure including an anode, a cathode, and an organic material layer between them.
  • the organic material layer is often composed of a multi-layer structure made of different materials to increase the efficiency and stability of the organic light-emitting device, and may be composed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer.
  • this organic light-emitting device when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode into the organic material layer. When the injected holes and electrons meet, an exciton is formed, and this exciton is When it falls back to the ground state, it glows.
  • Patent Document 1 KR 10-2014-0076888
  • This specification provides compounds and organic light-emitting devices containing the same.
  • An exemplary embodiment of the present specification provides a compound represented by the following formula (1).
  • R1 and R2 are the same or different from each other and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
  • At least one of R1 and R2 is an alkyl group having 1 to 3 carbon atoms
  • At least one of R2 is a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
  • R3 and R4 are the same or different from each other and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Or it is a substituted or unsubstituted aryl group, or combines with an adjacent group to form a substituted or unsubstituted hydrocarbon ring group,
  • R5 is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
  • R3 and R4 are substituted or unsubstituted aryl groups, or combine with adjacent groups to form a substituted or unsubstituted hydrocarbon ring group, at least one of R5 is a substituted or unsubstituted aryl group,
  • Ar1 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • L1 and L2 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
  • a is an integer from 1 to 8, and when a is 2 or more, R1 is the same or different,
  • b is an integer from 1 to 3, and when b is 2 or more, R2 is the same as or different from each other,
  • c is an integer from 1 to 7, and when c is 2 or more, R5 are the same or different.
  • an exemplary embodiment of the present specification includes an anode; cathode; and an organic light emitting device comprising at least one organic material layer provided between the anode and the cathode, wherein at least one layer of the organic material layer includes the compound represented by Formula 1.
  • the compounds described in this specification can be used as a material for the organic layer of an organic light-emitting device.
  • a compound according to at least one embodiment of the present specification may improve efficiency, low driving voltage, and/or lifespan characteristics in an organic light-emitting device.
  • the compounds described herein can be used as hole injection, hole transport, hole injection and hole transport, electron blocking, light emission, hole blocking, electron transport, or electron injection materials.
  • it compared to existing organic light emitting devices, it has the effects of low driving voltage, high efficiency, and/or long lifespan.
  • Figure 1 shows an example of an organic light-emitting device in which a substrate 1, an anode 2, an organic material layer 10, and a cathode 9 are sequentially stacked.
  • Figure 2 shows a substrate (1), anode (2), hole injection layer (3), hole transport layer (4), electron blocking layer (5), light emitting layer (6), hole blocking layer (7), electron injection and transport layer ( 8) and the cathode 9 are sequentially stacked.
  • substitution means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent.
  • the position to be substituted is not limited as long as it is the position where the hydrogen atom is substituted, that is, a position where the substituent can be substituted, and if two or more substituents are substituted. , two or more substituents may be the same or different from each other.
  • substituted or unsubstituted refers to deuterium; halogen group; Nitrile group (-CN); nitro group; hydroxyl group; Alkyl group; Cycloalkyl group; Alkoxy group; Phosphine oxide group; Aryloxy group; Alkylthioxy group; Arylthioxy group; Alkyl sulphoxy group; Aryl sulfoxy group; alkenyl group; silyl group; boron group; Amine group; Aryl group; Alternatively, it means that it is substituted with one or two or more substituents selected from the group consisting of heterocyclic groups, or is substituted with a substituent in which two or more of the above-exemplified substituents are linked, or does not have any substituents.
  • a substituent group in which two or more substituents are connected may be a biphenyl group. That is, the biphenyl group may be an aryl group, or it may be interpreted as a substituent in which two phenyl groups are connected.
  • substituted or unsubstituted refers to deuterium; halogen group; Nitrile group; nitro group; hydroxyl group; amino group; silyl group; boron group; Alkoxy group; Aryloxy group; Alkyl group; Cycloalkyl group; Aryl group; and a heterocyclic group, or is substituted with a substituent in which two or more of the above-exemplified substituents are linked, or does not have any substituent.
  • substituted or unsubstituted refers to deuterium; halogen group; Nitrile group; Alkyl group; Aryl group; and a heterocyclic group, or is substituted with a substituent in which two or more of the above-exemplified substituents are linked, or does not have any substituent.
  • halogen groups include fluorine (-F), chlorine (-Cl), bromine (-Br), or iodine (-I).
  • the silyl group may be represented by the formula -SiY a Y b Y c , where Y a , Y b and Y c are each hydrogen; Substituted or unsubstituted alkyl group; Or, it may be a substituted or unsubstituted aryl group.
  • the silyl group specifically includes, but is not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, and phenylsilyl group. No.
  • the boron group may be represented by the chemical formula -BY dY e , where Y d and Y e are each hydrogen; Substituted or unsubstituted alkyl group; Or, it may be a substituted or unsubstituted aryl group.
  • the boron group specifically includes, but is not limited to, trimethyl boron group, triethyl boron group, t-butyldimethyl boron group, triphenyl boron group, and phenyl boron group.
  • the alkyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the carbon number of the alkyl group is 1 to 30. According to another embodiment, the carbon number of the alkyl group is 1 to 20. According to another embodiment, the carbon number of the alkyl group is 1 to 10.
  • alkyl groups 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, etc., but are not limited to these.
  • the description of the alkyl group described above may be applied, except that the arylalkyl group is substituted with an aryl group.
  • the alkoxy group may be straight chain, branched chain, or ring chain.
  • the number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n.
  • Substituents containing alkyl groups, alkoxy groups, and other alkyl group moieties described in this specification include both straight-chain or branched forms.
  • the alkenyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms.
  • 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, etc., but are not limited to these.
  • the alkynyl group is a substituent containing a triple bond between carbon atoms, and may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkynyl group has 2 to 20 carbon atoms. According to another embodiment, the carbon number of the alkynyl group is 2 to 10.
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 6. Specifically, it includes cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, etc., but is not limited thereto.
  • the amine group is -NH 2
  • the amine group may be substituted with the above-described alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, and combinations thereof.
  • the number of carbon atoms of the substituted amine group is not particularly limited, but is preferably 1 to 30. According to one embodiment, the carbon number of the amine group is 1 to 20. According to one embodiment, the carbon number of the amine group is 1 to 10.
  • substituted amine groups include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, 9,9-dimethylfluorenylphenylamine group, pyridylphenylamine group, and diphenylamine.
  • phenylpyridylamine group phenylpyridylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, dibenzofuranylphenylamine group, 9-methylanthracenylamine group, diphenylamine group, phenylnaphthylamine group, Ditolylamine group, phenyltolylamine group, diphenylamine group, etc., but are not limited to these.
  • the aryl group is not particularly limited, but preferably has 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 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms.
  • the aryl group may be a monocyclic aryl group, such as a phenyl group, biphenyl group, terphenyl group, or quarterphenyl group, but is not limited thereto.
  • the polycyclic aryl group may include a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenyl group, chrysenyl group, fluorenyl group, triphenylenyl group, etc., but is not limited thereto. no.
  • the fluorenyl group may be substituted, and two substituents may be combined with each other to form a spiro structure.
  • the spiro structure may be an aromatic hydrocarbon ring or an aliphatic hydrocarbon ring.
  • fluorenyl group When the fluorenyl group is substituted, , , 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 to this.
  • a substituted aryl group may also include a form in which an aliphatic ring is condensed with an aryl group.
  • the tetrahydronaphthalene group of the structure below is included in the substituted aryl group.
  • one of the carbons of the benzene ring may be connected to another position.
  • the above-described description of the aryl group may be applied to the aryl group in the aryloxy group.
  • the above-described description of the alkyl group may be applied to the alkyl group among the alkylthioxy group and the alkylsulfoxy group.
  • the above-mentioned description of the aryl group may be applied to the aryl group among the arylthioxy group and the arylsulfoxy group.
  • the heterocyclic group is a cyclic group containing one or more of N, O, P, S, Si, and Se as heteroatoms, and the number of carbon atoms is not particularly limited, but it is preferably 2 to 60 carbon atoms. According to one embodiment, the carbon number of the heterocyclic group is 2 to 30. According to one embodiment, the carbon number of the heterocyclic group is 2 to 20.
  • heterocyclic groups include pyridine group, pyrrole group, pyrimidine group, quinoline group, pyridazinyl group, furan group, thiophene group, imidazole group, pyrazole group, dibenzofuran group, and dibenzothiophene group.
  • carbazole group benzocarbazole group, naphthobenzofuran group, benzonaphthothiophene group, indenocarbazole group, triazinyl group, etc., but is not limited to these.
  • heterocyclic group described above may be applied, except that the heteroaryl group is aromatic.
  • the description of the aryl group may be applied, except that the arylene group is divalent.
  • ring refers to a hydrocarbon ring; Or it means a heterocycle.
  • the hydrocarbon ring may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, and may be selected from examples of the cycloalkyl group or aryl group.
  • forming a ring by combining with adjacent groups means a substituted or unsubstituted aliphatic hydrocarbon ring by combining with adjacent groups; Substituted or unsubstituted aromatic hydrocarbon ring; Substituted or unsubstituted aliphatic heterocycle; Substituted or unsubstituted aromatic heterocycle; Or it means forming a condensation ring thereof.
  • the hydrocarbon ring refers to a ring consisting only of carbon and hydrogen atoms.
  • the heterocycle refers to a ring containing one or more elements selected from N, O, P, S, Si, and Se.
  • the aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic heterocycle, and aromatic heterocycle may be monocyclic or polycyclic.
  • an aliphatic hydrocarbon ring refers to a non-aromatic ring consisting only of carbon and hydrogen atoms.
  • Examples of aliphatic hydrocarbon rings include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, and cyclooctene. It is not limited to this.
  • an 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, etc., but are not limited thereto.
  • an aromatic hydrocarbon ring can be interpreted to have the same meaning as an aryl group.
  • an aliphatic heterocycle refers to an aliphatic ring containing one or more heteroatoms.
  • aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, and azocaine. , thiocane, etc., but is not limited thereto.
  • an aromatic heterocycle refers to an aromatic ring containing one or more heteroatoms.
  • aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, parazole, oxazole, isoxazole, thiazole, isothiazole, triazole, oxadiazole, and thiazole.
  • the compound represented by Formula 1 according to the present invention can control the energy barrier with the organic layer by adjusting the HOMO and LUMO energy levels of the compound by linking an amine group to tetrahydronaphthalene.
  • the compound represented by Formula 1 according to the present invention has an alkyl group substituent of 1 to 3 carbon atoms on tetrahydronaphthalene, or an alkyl group or aryl group substituent on the benzene ring portion of tetrahydronaphthalene, thereby enabling hole movement of the compound.
  • the hole and electron balance of the device can be adjusted.
  • the compound represented by Formula 1 according to the present invention can improve the driving voltage, efficiency, and lifespan of the device by improving hole transfer characteristics by linking an amine group to a substituted fluorenyl group.
  • R1 and R2 are the same or different from each other and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
  • At least one of R1 and R2 is an alkyl group having 1 to 3 carbon atoms
  • At least one of R2 is a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
  • R3 and R4 are the same or different from each other and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Or it is a substituted or unsubstituted aryl group, or combines with an adjacent group to form a substituted or unsubstituted hydrocarbon ring group,
  • R5 is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
  • R3 and R4 are substituted or unsubstituted aryl groups, or combine with adjacent groups to form a substituted or unsubstituted hydrocarbon ring group, at least one of R5 is a substituted or unsubstituted aryl group,
  • Ar1 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • L1 and L2 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
  • a is an integer from 1 to 8, and when a is 2 or more, R1 is the same or different,
  • b is an integer from 1 to 3, and when b is 2 or more, R2 is the same as or different from each other,
  • c is an integer from 1 to 7, and when c is 2 or more, R5 are the same or different.
  • R1 and R2 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Or it is a substituted or unsubstituted aryl group.
  • R1 and R2 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; Or it is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
  • R1 and R2 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or it is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • R1 and R2 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or it is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
  • R1 and R2 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; Or it is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.
  • R1 and R2 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 60 carbon atoms substituted or unsubstituted with deuterium; Or, it is an aryl group having 6 to 60 carbon atoms that is unsubstituted or substituted with deuterium.
  • R1 and R2 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 30 carbon atoms substituted or unsubstituted with deuterium; Or, it is an aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with deuterium.
  • R1 and R2 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 20 carbon atoms substituted or unsubstituted with deuterium; Or, it is an aryl group having 6 to 20 carbon atoms that is unsubstituted or substituted with deuterium.
  • R1 and R2 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 10 carbon atoms substituted or unsubstituted with deuterium; Or, it is an aryl group having 6 to 12 carbon atoms that is unsubstituted or substituted with deuterium.
  • R1 and R2 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 3 carbon atoms substituted or unsubstituted with deuterium; Or, it is an aryl group having 6 to 20 carbon atoms that is unsubstituted or substituted with deuterium.
  • R1 and R2 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 3 carbon atoms substituted or unsubstituted with deuterium; Or, it is an aryl group having 6 to 12 carbon atoms that is unsubstituted or substituted with deuterium.
  • R1 and R2 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 3 carbon atoms substituted or unsubstituted with deuterium; Or it is a phenyl group substituted or unsubstituted with deuterium.
  • R1 and R2 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 3 carbon atoms; Or it is a phenyl group.
  • R1 and R2 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; methyl group; ethyl group; profiler; isopropyl group; Or it is a phenyl group.
  • R1 and R2 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; methyl group; isopropyl group; Or it is a phenyl group.
  • At least one of R1 and R2 is an alkyl group having 1 to 3 carbon atoms.
  • At least one of R1 and R2 is a methyl group; ethyl group; Or it is an isopropyl group.
  • At least one of R1 and R2 is a methyl group; Or it is an isopropyl group.
  • At least one of R1 and R2 is a methyl group.
  • At least one of R2 is a substituted or unsubstituted alkyl group; Or it is a substituted or unsubstituted aryl group.
  • At least one of R2 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; Or it is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
  • At least one of R2 is a substituted or unsubstituted alkyl group having 1 to 3 carbon atoms; Or it is a substituted or unsubstituted aryl group having 6 to 10 carbon atoms.
  • At least one of R2 is a substituted or unsubstituted alkyl group having 1 to 3 carbon atoms; Or a substituted or unsubstituted phenyl group.
  • At least one of R2 is an alkyl group having 1 to 3 carbon atoms unsubstituted or substituted with deuterium; Or it is a phenyl group substituted or unsubstituted with deuterium.
  • At least one of R2 is an alkyl group having 1 to 3 carbon atoms; Or it is a phenyl group.
  • At least one of R2 is a methyl group; ethyl group; profiler; isopropyl group; Or it is a phenyl group.
  • At least one of R2 is a methyl group; isopropyl group; Or it is a phenyl group.
  • R1 is hydrogen; heavy hydrogen; or a methyl group
  • R2 is hydrogen; heavy hydrogen; methyl group; isopropyl group; Or it is a phenyl group.
  • R1 is hydrogen; or deuterium, and R2 is hydrogen; heavy hydrogen; methyl group; Or it is an isopropyl group.
  • R1 is hydrogen
  • R2 is hydrogen
  • methyl group Or it is an isopropyl group.
  • R1 is hydrogen
  • R2 is hydrogen
  • R1 is hydrogen
  • R2 is hydrogen
  • R1 is hydrogen
  • R2 is a methyl group; Or it is an isopropyl group.
  • R1 is hydrogen and R2 is a methyl group.
  • R1 is hydrogen and R2 is an isopropyl group.
  • R1 is a methyl group
  • R2 is hydrogen; heavy hydrogen; methyl group; isopropyl group; Or it is a phenyl group.
  • R1 is a methyl group
  • R2 is a methyl group
  • it is an isopropyl group
  • R1 is a methyl group
  • R2 is a phenyl group
  • R3 and R4 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Or, it is a substituted or unsubstituted aryl group, or combines with adjacent groups to form a substituted or unsubstituted hydrocarbon ring group.
  • R3 and R4 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; Alternatively, it is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or is combined with adjacent groups to form a substituted or unsubstituted hydrocarbon ring group having 6 to 60 carbon atoms.
  • R3 and R4 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Alternatively, it is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or is combined with adjacent groups to form a substituted or unsubstituted hydrocarbon ring group having 6 to 30 carbon atoms.
  • R3 and R4 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Alternatively, it is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or is combined with adjacent groups to form a substituted or unsubstituted hydrocarbon ring group having 6 to 20 carbon atoms.
  • R3 and R4 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; Or, it is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, or is combined with adjacent groups to form a substituted or unsubstituted hydrocarbon ring group having 6 to 12 carbon atoms.
  • R3 and R4 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 60 carbon atoms substituted or unsubstituted with deuterium; Alternatively, it is an aryl group having 6 to 60 carbon atoms that is unsubstituted or substituted with deuterium, or is bonded to an adjacent group to form a hydrocarbon ring group having 6 to 60 carbon atoms that is unsubstituted or substituted with deuterium.
  • R3 and R4 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 30 carbon atoms substituted or unsubstituted with deuterium; Or, it is an aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with deuterium, or is bonded to an adjacent group to form a hydrocarbon ring group having 6 to 30 carbon atoms that is unsubstituted or substituted with deuterium.
  • R3 and R4 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 20 carbon atoms substituted or unsubstituted with deuterium; Alternatively, it is an aryl group having 6 to 20 carbon atoms that is unsubstituted or substituted with deuterium, or is bonded to an adjacent group to form a hydrocarbon ring group having 6 to 20 carbon atoms that is unsubstituted or substituted with deuterium.
  • R3 and R4 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 10 carbon atoms substituted or unsubstituted with deuterium; Or, it is an aryl group having 6 to 12 carbon atoms that is unsubstituted or substituted with deuterium, or is bonded to an adjacent group to form a hydrocarbon ring group having 6 to 12 carbon atoms that is unsubstituted or substituted with deuterium.
  • R3 and R4 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 3 carbon atoms substituted or unsubstituted with deuterium; Alternatively, it is an aryl group having 6 to 20 carbon atoms that is unsubstituted or substituted with deuterium, or is bonded to an adjacent group to form a hydrocarbon ring group having 6 to 20 carbon atoms that is unsubstituted or substituted with deuterium.
  • R3 and R4 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 3 carbon atoms substituted or unsubstituted with deuterium; Or, it is an aryl group having 6 to 12 carbon atoms that is unsubstituted or substituted with deuterium, or is bonded to an adjacent group to form a hydrocarbon ring group having 6 to 12 carbon atoms that is unsubstituted or substituted with deuterium.
  • R3 and R4 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 3 carbon atoms substituted or unsubstituted with deuterium; Alternatively, it is a phenyl group substituted or unsubstituted with deuterium, or it combines with adjacent groups to form a spiro structure substituted or unsubstituted with deuterium.
  • R3 and R4 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; an alkyl group having 1 to 3 carbon atoms; Or, it is a phenyl group, or combines with adjacent groups to form a spiro structure.
  • R3 and R4 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; methyl group; ethyl group; profiler; isopropyl group; Or, it is a phenyl group, or combines with adjacent groups to form a spiro structure.
  • R3 and R4 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; methyl group; Or, it is a phenyl group, or combines with adjacent groups to form a spiro structure.
  • R3 and R4 are the same or different from each other, and are each independently a methyl group; Or, it is a phenyl group, or combines with adjacent groups to form a spiro structure.
  • the spiro structure is a spirofluorenyl group ( ) can be formed.
  • R5 is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Or it is a substituted or unsubstituted aryl group.
  • R5 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; Or it is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
  • R5 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or it is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • R5 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or it is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
  • R5 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; Or it is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.
  • R5 is hydrogen; heavy hydrogen; Or it is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.
  • R5 is hydrogen; heavy hydrogen; An alkyl group having 1 to 60 carbon atoms substituted or unsubstituted with deuterium; Or, it is an aryl group having 6 to 60 carbon atoms that is unsubstituted or substituted with deuterium.
  • R5 is hydrogen; heavy hydrogen; An alkyl group having 1 to 30 carbon atoms substituted or unsubstituted with deuterium; Or, it is an aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with deuterium.
  • R5 is hydrogen; heavy hydrogen; An alkyl group having 1 to 20 carbon atoms substituted or unsubstituted with deuterium; Or, it is an aryl group having 6 to 20 carbon atoms that is unsubstituted or substituted with deuterium.
  • R5 is hydrogen; heavy hydrogen; An alkyl group having 1 to 10 carbon atoms substituted or unsubstituted with deuterium; Or, it is an aryl group having 6 to 12 carbon atoms that is unsubstituted or substituted with deuterium.
  • R5 is hydrogen; heavy hydrogen; Or, it is an aryl group having 6 to 12 carbon atoms that is unsubstituted or substituted with deuterium.
  • R5 is hydrogen; heavy hydrogen; An alkyl group having 1 to 3 carbon atoms substituted or unsubstituted with deuterium; Or, it is an aryl group having 6 to 20 carbon atoms that is unsubstituted or substituted with deuterium.
  • R5 is hydrogen; heavy hydrogen; An alkyl group having 1 to 3 carbon atoms substituted or unsubstituted with deuterium; Or, it is an aryl group having 6 to 12 carbon atoms that is unsubstituted or substituted with deuterium.
  • R5 is hydrogen; heavy hydrogen; Or, it is an aryl group having 6 to 12 carbon atoms that is unsubstituted or substituted with deuterium.
  • R5 is hydrogen; heavy hydrogen; A phenyl group substituted or unsubstituted with deuterium; Biphenyl group substituted or unsubstituted with deuterium; Or it is a naphthyl group substituted or unsubstituted with deuterium.
  • R5 is hydrogen; heavy hydrogen; phenyl group; Biphenyl group; Or it is a naphthyl group.
  • R3 and R4 are substituted or unsubstituted aryl groups, or when they combine with adjacent groups to form a substituted or unsubstituted hydrocarbon ring group, at least one of R5 is a substituted or unsubstituted aryl group. It's awesome.
  • R3 and R4 are substituted or unsubstituted aryl groups or combine with adjacent groups to form a substituted or unsubstituted hydrocarbon ring group
  • at least one of R5 has a substituted or unsubstituted carbon number It is an aryl group of 6 to 60.
  • R3 and R4 are substituted or unsubstituted aryl groups or combine with adjacent groups to form a substituted or unsubstituted hydrocarbon ring group
  • at least one of R5 has a substituted or unsubstituted carbon number It is an aryl group of 6 to 30.
  • R3 and R4 are substituted or unsubstituted aryl groups or combine with adjacent groups to form a substituted or unsubstituted hydrocarbon ring group
  • at least one of R5 has a substituted or unsubstituted carbon number It is an aryl group of 6 to 20.
  • R3 and R4 are substituted or unsubstituted aryl groups or combine with adjacent groups to form a substituted or unsubstituted hydrocarbon ring group
  • at least one of R5 has a substituted or unsubstituted carbon number It is an aryl group of 6 to 12.
  • R3 and R4 are substituted or unsubstituted aryl groups or combine with adjacent groups to form a substituted or unsubstituted hydrocarbon ring group
  • at least one of R5 is substituted or unsubstituted with deuterium. It is an aryl group having 6 to 30 carbon atoms.
  • R3 and R4 are substituted or unsubstituted aryl groups or combine with adjacent groups to form a substituted or unsubstituted hydrocarbon ring group
  • at least one of R5 is substituted or unsubstituted with deuterium. It is an aryl group having 6 to 20 carbon atoms.
  • R3 and R4 are substituted or unsubstituted aryl groups or combine with adjacent groups to form a substituted or unsubstituted hydrocarbon ring group
  • at least one of R5 is substituted or unsubstituted with deuterium. It is an aryl group having 6 to 12 carbon atoms.
  • R3 and R4 when R3 and R4 are substituted or unsubstituted aryl groups or combine with adjacent groups to form a substituted or unsubstituted hydrocarbon ring group, at least one of R5 is substituted or unsubstituted with deuterium.
  • R3 and R4 are substituted or unsubstituted aryl groups, or combine with adjacent groups to form a substituted or unsubstituted hydrocarbon ring group
  • at least one of R5 is a phenyl group; Biphenyl group; Or it is a naphthyl group.
  • L1 and L2 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted arylene group; Or it is a substituted or unsubstituted divalent heterocyclic group.
  • L1 and L2 are the same or different from each other and are each independently directly bonded; A substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or it is a substituted or unsubstituted divalent heterocyclic group having 2 to 60 carbon atoms.
  • L1 and L2 are the same or different from each other and are each independently directly bonded; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted divalent heterocyclic group having 2 to 30 carbon atoms.
  • L1 and L2 are the same or different from each other and are each independently directly bonded; A substituted or unsubstituted arylene group having 6 to 20 carbon atoms; Or it is a substituted or unsubstituted divalent heterocyclic group having 2 to 20 carbon atoms.
  • L1 and L2 are the same or different from each other and are each independently directly bonded; A substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or it is a substituted or unsubstituted divalent heterocyclic group containing O, S or N and having 2 to 60 carbon atoms.
  • L1 and L2 are the same or different from each other and are each independently directly bonded; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted divalent heterocyclic group containing O, S or N and having 2 to 30 carbon atoms.
  • L1 and L2 are the same or different from each other and are each independently directly bonded; A substituted or unsubstituted arylene group having 6 to 20 carbon atoms; Or it is a substituted or unsubstituted divalent heterocyclic group containing O, S or N and having 2 to 20 carbon atoms.
  • L1 and L2 are the same or different from each other and are each independently directly bonded; Or it is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
  • L1 and L2 are the same or different from each other and are each independently directly bonded; Or, it is an arylene group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium or an alkyl group.
  • L1 and L2 are the same or different from each other and are each independently directly bonded; Or, it is an arylene group having 6 to 30 carbon atoms that is substituted or unsubstituted with deuterium or an alkyl group having 1 to 30 carbon atoms.
  • L1 and L2 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted phenylene group; Substituted or unsubstituted biphenylylene group; Or it is a substituted or unsubstituted divalent fluorenyl group.
  • L1 and L2 are the same or different from each other and are each independently directly bonded; Or, it is an arylene group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium.
  • L1 and L2 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted phenylene group; Or a substituted or unsubstituted biphenylylene group.
  • L1 and L2 are the same or different from each other and are each independently directly bonded; A phenylene group substituted or unsubstituted with deuterium or an alkyl group; Or it is a biphenylylene group substituted or unsubstituted with deuterium or an alkyl group.
  • L1 and L2 are the same or different from each other and are each independently directly bonded; A phenylene group substituted or unsubstituted with deuterium or an alkyl group having 1 to 10 carbon atoms; Or it is a biphenylylene group substituted or unsubstituted with deuterium or an alkyl group having 1 to 10 carbon atoms.
  • L1 and L2 are the same or different from each other and are each independently directly bonded; A phenylene group substituted or unsubstituted with deuterium or an alkyl group having 1 to 3 carbon atoms; Or it is a biphenylylene group substituted or unsubstituted with deuterium or an alkyl group having 1 to 3 carbon atoms.
  • L1 and L2 are the same or different from each other and are each independently directly bonded; A phenylene group substituted or unsubstituted with deuterium or methyl group; Or it is a biphenylylene group substituted or unsubstituted with deuterium or methyl group.
  • L1 and L2 are the same or different from each other and are each independently directly bonded; A phenylene group substituted or unsubstituted with a methyl group; Or it is a biphenylylene group substituted or unsubstituted with a methyl group.
  • L1 and L2 are the same or different from each other and are each independently directly bonded; A phenylene group substituted or unsubstituted with a methyl group; Or it is a biphenylylene group.
  • L1 and L2 are the same or different from each other and are each independently directly bonded; A phenylene group substituted or unsubstituted with deuterium; Or it is a biphenylylene group substituted or unsubstituted with deuterium.
  • L1 and L2 are the same or different from each other and are each independently directly bonded; phenylene group; Or it is a biphenylylene group.
  • L1 and L2 are the same and are directly bonded; Or a substituted or unsubstituted phenyl group.
  • L1 and L2 are the same and are directly bonded; Or it is a phenyl group substituted or unsubstituted with deuterium.
  • L1 and L2 are the same and are directly bonded; Or it is a phenyl group.
  • L1 and L2 are the same and are directly bonded to each other.
  • L1 is a direct bond; Or a substituted or unsubstituted phenyl group.
  • L1 is a direct bond; Or it is a phenyl group substituted or unsubstituted with deuterium.
  • L1 is a direct bond; Or it is a phenyl group.
  • L1 is a direct bond
  • L2 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted phenylene group; Or a substituted or unsubstituted biphenylylene group.
  • L2 are the same or different from each other and are each independently directly bonded; A phenylene group substituted or unsubstituted with deuterium or an alkyl group; Or it is a biphenylylene group substituted or unsubstituted with deuterium or an alkyl group.
  • L2 are the same or different from each other and are each independently directly bonded; A phenylene group substituted or unsubstituted with deuterium or methyl group; Or it is a biphenylene group substituted or unsubstituted with deuterium or methyl group.
  • L2 are the same or different from each other and are each independently directly bonded; A phenylene group substituted or unsubstituted with a methyl group; Or it is a biphenylylene group.
  • L2 are the same or different from each other and are each independently directly bonded; phenylene group; Or it is a biphenylylene group.
  • L2 is a direct bond
  • Ar1 is a substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heterocyclic group.
  • Ar1 is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or it is a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
  • Ar1 is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
  • Ar1 is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or it is a substituted or unsubstituted O, S or N containing heterocyclic group having 2 to 60 carbon atoms.
  • Ar1 is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted O, S or N containing heterocyclic group having 2 to 30 carbon atoms.
  • Ar1 is an arylene group having 6 to 60 carbon atoms substituted or unsubstituted with deuterium, an alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms; or an O, S or N-containing heterocyclic group having 2 to 60 carbon atoms that is substituted or unsubstituted with deuterium, an alkyl group with 1 to 30 carbon atoms, or an aryl group with 6 to 30 carbon atoms.
  • Ar1 is an arylene group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium, an alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms; or an O, S or N-containing heterocyclic group having 2 to 30 carbon atoms that is substituted or unsubstituted with deuterium, an alkyl group with 1 to 30 carbon atoms, or an aryl group with 6 to 30 carbon atoms.
  • Ar1 is an arylene group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms; or an O, S or N-containing heterocyclic group having 2 to 30 carbon atoms, substituted or unsubstituted with deuterium, an alkyl group with 1 to 20 carbon atoms, or an aryl group with 6 to 20 carbon atoms.
  • Ar1 is an arylene group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms; Or, it is a heterocyclic group containing O, S or N of 2 to 30 carbon atoms, substituted or unsubstituted with deuterium, an alkyl group of 1 to 10 carbon atoms, or an aryl group of 6 to 12 carbon atoms.
  • Ar1 is an arylene group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium, an alkyl group having 1 to 3 carbon atoms, or an aryl group having 6 to 10 carbon atoms; or an O, S or N-containing heterocyclic group having 2 to 30 carbon atoms, substituted or unsubstituted with deuterium, an alkyl group with 1 to 3 carbon atoms, or an aryl group with 6 to 10 carbon atoms.
  • Ar1 is an arylene group having 6 to 20 carbon atoms substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms; or an O, S or N-containing heterocyclic group having 2 to 20 carbon atoms, substituted or unsubstituted with deuterium, an alkyl group with 1 to 10 carbon atoms, or an aryl group with 6 to 12 carbon atoms.
  • Ar1 is an arylene group having 6 to 20 carbon atoms substituted or unsubstituted with deuterium, an alkyl group having 1 to 3 carbon atoms, or an aryl group having 6 to 10 carbon atoms; or an O, S or N-containing heterocyclic group having 2 to 20 carbon atoms that is substituted or unsubstituted with deuterium, an alkyl group with 1 to 3 carbon atoms, or an aryl group with 6 to 10 carbon atoms.
  • Ar1 is an arylene group having 6 to 20 carbon atoms substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms; Or it is an O, S or N-containing heterocyclic group having 2 to 20 carbon atoms that is substituted or unsubstituted with deuterium.
  • Ar1 is an arylene group having 6 to 20 carbon atoms substituted or unsubstituted with deuterium, an alkyl group having 1 to 3 carbon atoms, or an aryl group having 6 to 10 carbon atoms; Or it is an O, S or N-containing heterocyclic group having 2 to 20 carbon atoms that is substituted or unsubstituted with deuterium.
  • Ar1 is a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted triphenylene group; Substituted or unsubstituted tetrahydronaphthalene group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted carbazole group.
  • Ar1 is a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted tetrahydronaphthalene group; Substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group.
  • Ar1 is a phenyl group unsubstituted or substituted with deuterium; Biphenyl group substituted or unsubstituted with deuterium; Terphenyl group substituted or unsubstituted with deuterium; Naphthyl group substituted or unsubstituted with deuterium; A phenanthrenyl group substituted or unsubstituted with deuterium; A tetrahydronaphthalene group substituted or unsubstituted with one or more substituents from the group consisting of deuterium, an alkyl group with 1 to 10 carbon atoms, and an aryl group with 6 to 20 carbon atoms; Dibenzofuran group substituted or unsubstituted with deuterium; Or it is a dibenzothiophene group substituted or unsubstituted with deuterium.
  • Ar1 is a phenyl group unsubstituted or substituted with deuterium; Biphenyl group substituted or unsubstituted with deuterium; Terphenyl group substituted or unsubstituted with deuterium; Naphthyl group substituted or unsubstituted with deuterium; A phenanthrenyl group substituted or unsubstituted with deuterium; A tetrahydronaphthalene group substituted or unsubstituted with one or more substituents from the group consisting of deuterium, an alkyl group with 1 to 3 carbon atoms, and an aryl group with 6 to 12 carbon atoms; Dibenzofuran group substituted or unsubstituted with deuterium; Or it is a dibenzothiophene group substituted or unsubstituted with deuterium.
  • Ar1 is a phenyl group unsubstituted or substituted with deuterium; Biphenyl group substituted or unsubstituted with deuterium; Terphenyl group substituted or unsubstituted with deuterium; Naphthyl group substituted or unsubstituted with deuterium; A phenanthrenyl group substituted or unsubstituted with deuterium; A tetrahydronaphthalene group substituted or unsubstituted with one or more substituents from the group consisting of deuterium, methyl group, isopropyl group, and phenyl group; Dibenzofuran group substituted or unsubstituted with deuterium; Or it is a dibenzothiophene group substituted or unsubstituted with deuterium.
  • Ar1 is a phenyl group; Biphenyl group; Terphenyl group; naphthyl group; phenanthrenyl group; triphenylene group; A tetrahydronaphthalene group substituted or unsubstituted with one or more substituents from the group consisting of methyl group, isopropyl group, and phenyl group; Dibenzofuran group; Dibenzothiophene group; Or it is a carbazole group.
  • Ar1 is a phenyl group; Biphenyl group; Terphenyl group; naphthyl group; phenanthrenyl group; A tetrahydronaphthalene group substituted or unsubstituted with one or more substituents from the group consisting of methyl group, isopropyl group, and phenyl group; Dibenzofuran group; Or it is a dibenzothiophene group.
  • a is an integer from 1 to 8.
  • a is an integer from 1 to 4.
  • a is 8.
  • a is 7.
  • a is 6.
  • a is 5.
  • a is 4.
  • a is 3.
  • a is 2.
  • a is 1.
  • b is an integer of 1 to 3.
  • b is 3.
  • b is 2.
  • b is 1.
  • c is an integer from 1 to 7.
  • c 7.
  • c is 6.
  • c is 5.
  • c is 4.
  • c is 3.
  • c is 2.
  • c is 1.
  • Formula 1 is represented by Formula 2 below.
  • R1 to R5, L1, L2, Ar1, and a to c are the same as those in Formula 1 above.
  • Formula 1 is represented by Formula 3 below.
  • R1, R2, L1, L2, Ar1, a and b are the same as those in Formula 1 above,
  • R3 and R4 are the same or different from each other and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Or it is a substituted or unsubstituted aryl group, or combines with an adjacent group to form a substituted or unsubstituted hydrocarbon ring group,
  • R5' is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
  • R5' is a substituted or unsubstituted aryl group.
  • R5' is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; Or it is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
  • R5' is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or it is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • R5' is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or it is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
  • R5' is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; Or it is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.
  • R5' is hydrogen; heavy hydrogen; Or it is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.
  • R5' is hydrogen; heavy hydrogen; An alkyl group having 1 to 60 carbon atoms substituted or unsubstituted with deuterium; Or, it is an aryl group having 6 to 60 carbon atoms that is unsubstituted or substituted with deuterium.
  • R5' is hydrogen; heavy hydrogen; An alkyl group having 1 to 30 carbon atoms substituted or unsubstituted with deuterium; Or, it is an aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with deuterium.
  • R5' is hydrogen; heavy hydrogen; An alkyl group having 1 to 20 carbon atoms substituted or unsubstituted with deuterium; Or, it is an aryl group having 6 to 20 carbon atoms that is unsubstituted or substituted with deuterium.
  • R5' is hydrogen; heavy hydrogen; An alkyl group having 1 to 10 carbon atoms substituted or unsubstituted with deuterium; Or, it is an aryl group having 6 to 12 carbon atoms that is unsubstituted or substituted with deuterium.
  • R5' is hydrogen; heavy hydrogen; Or, it is an aryl group having 6 to 12 carbon atoms that is unsubstituted or substituted with deuterium.
  • R5' is hydrogen; heavy hydrogen; An alkyl group having 1 to 3 carbon atoms substituted or unsubstituted with deuterium; Or, it is an aryl group having 6 to 20 carbon atoms that is unsubstituted or substituted with deuterium.
  • R5' is hydrogen; heavy hydrogen; An alkyl group having 1 to 3 carbon atoms substituted or unsubstituted with deuterium; Or, it is an aryl group having 6 to 12 carbon atoms that is unsubstituted or substituted with deuterium.
  • R5' is hydrogen; heavy hydrogen; Or, it is an aryl group having 6 to 12 carbon atoms that is unsubstituted or substituted with deuterium.
  • R5' is hydrogen; heavy hydrogen; A phenyl group substituted or unsubstituted with deuterium; Biphenyl group substituted or unsubstituted with deuterium; Or it is a naphthyl group substituted or unsubstituted with deuterium.
  • R5' is hydrogen; heavy hydrogen; phenyl group; Biphenyl group; Or it is a naphthyl group.
  • Formula 1 is represented by the following Formula 1-1.
  • R1, R3 to R5, L1, L2, Ar1, a and c are the same as those in Formula 1 above,
  • R2' is a substituted or unsubstituted alkyl group; Or it is a substituted or unsubstituted aryl group.
  • R2' is a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; Or it is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
  • R2' is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or it is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • R2' is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or it is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
  • R2' is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; Or it is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.
  • R2' is a substituted or unsubstituted alkyl group having 1 to 3 carbon atoms; Or it is a substituted or unsubstituted aryl group having 6 to 10 carbon atoms.
  • R2' is a substituted or unsubstituted alkyl group having 1 to 3 carbon atoms; Or a substituted or unsubstituted phenyl group.
  • R2' is an alkyl group having 1 to 60 carbon atoms unsubstituted or substituted with deuterium; Or, it is an aryl group having 6 to 60 carbon atoms that is unsubstituted or substituted with deuterium.
  • R2' is an alkyl group having 1 to 30 carbon atoms unsubstituted or substituted with deuterium; Or, it is an aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with deuterium.
  • R2' is an alkyl group having 1 to 20 carbon atoms unsubstituted or substituted with deuterium; Or, it is an aryl group having 6 to 20 carbon atoms that is unsubstituted or substituted with deuterium.
  • R2' is an alkyl group having 1 to 10 carbon atoms unsubstituted or substituted with deuterium; Or, it is an aryl group having 6 to 12 carbon atoms that is unsubstituted or substituted with deuterium.
  • R2' is an alkyl group having 1 to 3 carbon atoms unsubstituted or substituted with deuterium; Or, it is an aryl group having 6 to 10 carbon atoms that is unsubstituted or substituted with deuterium.
  • R2' is an alkyl group having 1 to 3 carbon atoms unsubstituted or substituted with deuterium; Or it is a phenyl group substituted or unsubstituted with deuterium.
  • R2' is a methyl group; ethyl group; profiler; isopropyl group; Or it is a phenyl group substituted or unsubstituted with deuterium.
  • R2' is a methyl group; ethyl group; profiler; isopropyl group; Or it is a phenyl group.
  • R2' is a methyl group; isopropyl group; Or it is a phenyl group.
  • R2' is a methyl group; Or it is a phenyl group.
  • Formula 1 is represented by any one of the following Formulas 2-1 to 2-3.
  • R1 to R5, L1, L2, Ar1, and a to c are the same as those in Formula 1 above.
  • Formula 1 is represented by any one of the following Formulas 2-1, 2-2, and 2-3-1.
  • R1 to R5, L1, L2, Ar1, and a to c are the same as those in Formula 1 above.
  • Formula 1 is represented by the following Formula 3-1 or 3-2.
  • R1 to R5, L1, L2, Ar1, and a to c are the same as those in Formula 1 above.
  • Formula 1 is represented by any one of the following compounds.
  • the compound represented by Chemical Formula 1 may have a core structure prepared as shown in Scheme 1 below. Substituents may be combined by methods known in the art, and the type, position, or number of substituents may be changed according to techniques known in the art.
  • X may be a halogen group such as Cl, Br, or I.
  • Scheme 1 illustrates the process of synthesizing a compound in which a specific substituent is bound to a specific position
  • the method of formula 1 above can be obtained by using starting materials, intermediates, etc. known in the art, using synthetic methods known in the art. Compounds that fall within the range can be synthesized.
  • compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure of the compound represented by Formula 1 above.
  • the HOMO and LUMO energy levels of the compound can be adjusted by introducing various substituents into the core structure of the above structure.
  • the present specification provides an organic light-emitting device containing the above-mentioned compound.
  • the organic light emitting device includes an anode; cathode; And an organic light-emitting device comprising at least one organic material layer provided between the anode and the cathode, wherein at least one layer of the organic material layer includes a compound represented by the above-mentioned formula (1).
  • the organic light-emitting device of the present specification can be manufactured using conventional organic light-emitting device manufacturing methods and materials, except that the organic material layer is formed using the compound of Formula 1 described above.
  • the compound may be formed into 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 application method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.
  • the organic material layer of the organic light emitting device of the present specification may have a single-layer structure, or may have a multi-layer 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 the organic material layer, a hole transport layer, a hole injection layer, an electron blocking layer, a hole transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron injection and transport layer. It can have a structure that does.
  • the structure of the organic light emitting device of the present specification is not limited to this and may include fewer or more organic material layers.
  • the organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer is a compound represented by the above-mentioned formula 1. It can be included.
  • the organic material layer includes a hole transport layer or a hole injection layer
  • the hole transport layer or the hole injection layer may include a compound represented by the above-described formula (1).
  • the organic material layer includes an electron blocking layer, and the electron blocking layer includes the compound represented by Formula 1.
  • the organic material layer includes an electron injection layer, an electron transport layer, an electron transport and injection layer, or a hole blocking layer, and the electron injection layer, the electron transport layer, the electron transport and injection layer, or the hole blocking layer is It may include a compound represented by the above-mentioned formula (1).
  • the organic material layer includes an electron transport layer, an electron injection layer, or an electron transport and injection layer
  • the electron transport layer, an electron injection layer, or an electron transport and injection layer is represented by the above-mentioned formula (1) It may contain compounds.
  • the organic material layer includes an electron control layer
  • the electron control layer may include a compound represented by the above-described Chemical Formula 1.
  • the organic material layer includes a hole blocking layer
  • the hole blocking layer includes the compound represented by Formula 1.
  • the organic material layer is an electron transport and injection layer
  • the electron transport and injection layer includes the compound represented by the above-described formula (1).
  • the thickness of the organic material layer containing the compound of Formula 1 is 5 ⁇ to 300 ⁇ , preferably 10 ⁇ to 300 ⁇ , and more preferably 10 ⁇ to 200 ⁇ .
  • the organic material layer includes a light-emitting layer, and the light-emitting layer includes the compound represented by the above-described formula (1).
  • the organic material layer includes a light-emitting layer, and the light-emitting layer includes the compound represented by the above-described formula 1 as a host.
  • the organic material layer includes a light-emitting layer, and the light-emitting layer includes the compound represented by the above-described formula (1) as a dopant.
  • the organic layer may further include other organic compounds, metals, or metal compounds in addition to the compound represented by Formula 1 described above.
  • the light emitting layer further includes a fluorescent dopant or a phosphorescent dopant.
  • the dopant in the light emitting layer is included in an amount of 1 to 50 parts by weight based on 100 parts by weight of the host.
  • the organic layer includes a light-emitting layer
  • the light-emitting layer includes the compound represented by Formula 1 as a host, and may further include an additional host.
  • the organic material layer includes a light-emitting layer, and the light-emitting layer includes an anthracene-based compound.
  • the organic material layer includes a light-emitting layer, and the light-emitting layer includes an anthracene-based compound as a host.
  • the organic material layer includes a light-emitting layer, and the light-emitting layer includes an anthracene-based compound as a host and further includes a dopant.
  • the dopant includes an arylamine-based compound, a heterocyclic compound containing boron and nitrogen, or an Ir complex.
  • the organic layer includes a light-emitting layer
  • the light-emitting layer includes an anthracene-based compound as a host and an arylamine-based compound as a dopant.
  • the organic light emitting device of the present specification includes a hole transport layer, a hole injection layer, an electron blocking layer, an electron injection and transport layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole transport and injection layer. It may further include one or more organic layers.
  • the organic light emitting device includes an anode; cathode; and two or more organic layers provided between the anode and the cathode, wherein at least one of the two or more organic layers includes the compound represented by Formula 1.
  • the two or more organic layers may be selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, a hole transport and injection layer, and an electron blocking layer.
  • the two or more organic layers may be selected from the group consisting of a light emitting layer, an electron transport layer, an electron injection layer, an electron transport and injection layer, an electron control layer, and a hole blocking layer.
  • the organic material layer includes two or more electron transport layers, and at least one of the two or more electron transport layers includes the compound represented by Formula 1.
  • the compound represented by Formula 1 may be included in one of the two or more electron transport layers, and may be included in each of the two or more electron transport layers.
  • the electron transport layer, the electron injection layer, or the electron transport and injection layer may further include an n-type dopant.
  • the n-type dopant may be one known in the art, for example, a metal or a metal complex.
  • the electron transport layer including the compound represented by Formula 1 may further include Lithium Quinolate (LiQ).
  • the compound represented by Formula 1 and the n-type dopant may be included in a weight ratio of 2:8 to 8:2, for example, 4:6 to 6:4.
  • the compound represented by Formula 1 and the n-type dopant may be included in a weight ratio of 1:1.
  • the organic layer includes two or more hole transport layers, and at least one of the two or more hole transport layers includes the compound represented by Formula 1.
  • the compound represented by Formula 1 may be included in one of the two or more hole transport layers, and may be included in each of the two or more hole transport layers.
  • the organic material layer further includes a hole injection layer or a hole transport layer including a compound including an arylamine group, carbazolyl group, or benzocarbazolyl group in addition to the organic material layer including the compound represented by Formula 1. It can be included.
  • the organic light emitting device may be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting device may be an inverted type organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
  • the organic material layer may include an electron blocking layer, and materials known in the art may be used as the electron blocking layer.
  • the organic light emitting device may have, for example, a stacked structure as shown below, but is not limited thereto.
  • the structure of the organic light emitting device of this specification may have the same structure as shown in FIGS. 1 and 2, but is not limited thereto.
  • Figure 1 illustrates the structure of an organic light-emitting device in which a substrate 1, an anode 2, an organic material layer 10, and a cathode 9 are sequentially stacked.
  • the compound may be included in the organic layer 10.
  • Figure 2 shows a substrate (1), anode (2), hole injection layer (3), hole transport layer (4), electron blocking layer (5), light emitting layer (6), hole blocking layer (7), electron injection and transport layer ( The structure of an organic light emitting device in which 8) and cathode 9 are sequentially stacked is illustrated.
  • the compound is included in the hole injection layer (3), the hole transport layer (4), the electron blocking layer (5), the light emitting layer (6), the hole blocking layer (7), or the electron injection and transport layer (8). You can.
  • the electron blocking layer and the light emitting layer may be provided adjacent to each other.
  • the electron blocking layer and the light emitting layer may be provided in physical contact.
  • the hole transport layer and the electron blocking layer may be provided adjacent to each other.
  • the hole transport layer and the electron blocking layer may be provided in physical contact.
  • the organic light emitting device of the present specification can be manufactured using materials and methods known in the art, except that at least one layer of the organic material layer contains the above compound, that is, the compound represented by Chemical Formula 1.
  • the organic material layers may be formed of the same material or different materials.
  • the organic light emitting device uses a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to deposit a metal, a conductive metal oxide, or an alloy thereof on a substrate.
  • a PVD physical vapor deposition
  • 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 on it. It can be.
  • an organic light-emitting device can also be made by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the organic material layer may further include one or more of a hole transport layer, a hole injection layer, an electron blocking layer, an electron injection and transport 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 multi-layer structure including a hole injection layer, a hole transport layer, an electron injection and transport layer, an electron blocking layer, a light emitting layer and an electron transport layer, an electron injection layer, an electron injection and transport layer, etc., but is not limited to this and may have a single-layer structure. there is.
  • the organic material layer uses a variety of polymer materials to form a smaller number of layers by using a solvent process rather than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer. It can be manufactured in layers.
  • the anode is an electrode that injects holes
  • the anode material is generally preferably a material with a large work function to ensure smooth hole injection into the organic layer.
  • anode materials 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); Combination of metal and oxide such as ZnO:Al or SnO 2 :Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline are included, but are not limited to these.
  • the cathode is an electrode that injects electrons
  • the cathode material is generally preferably a material with a small work function to facilitate electron injection into the organic layer.
  • Specific examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; There are, but are not limited to, multi-layered materials such as LiF/Al or LiO 2 /Al.
  • the hole injection layer is a layer that serves to facilitate the injection of holes from the anode to the light emitting layer, and the hole injection material is a material that can well inject holes from the anode at a low voltage.
  • the hole injection material is HOMO (highest occupied). It is preferable that the molecular orbital is between the work function of the anode material and the HOMO of the surrounding organic layer.
  • Specific examples of hole injection materials include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrilehexaazatriphenylene-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. If the thickness of the hole injection layer is 1 nm or more, there is an advantage in preventing the hole injection characteristics from deteriorating, and if it is 150 nm or less, the thickness of the hole injection layer is so thick that the driving voltage is increased to improve the movement of holes. There is an advantage to preventing this.
  • the hole transport layer may play a role in facilitating the transport of holes.
  • the hole transport material is a material that can transport holes from the anode or hole injection layer and transfer them to the light emitting layer, and a material with high mobility for holes is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers with both conjugated and non-conjugated portions, but are not limited to these.
  • An additional hole buffer layer may be provided between the hole injection layer and the hole transport layer, and may include hole injection or transport materials known in the art.
  • An electron blocking layer may be provided between the hole transport layer and the light emitting layer.
  • the above-described compounds or materials known in the art may be used in the electron blocking layer.
  • the light-emitting 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 the visible range by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and is preferably a material with good quantum efficiency for fluorescence or phosphorescence.
  • Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); Carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV) series polymer; Spiro compounds; Polyfluorene, rubrene, etc., but are not limited to these.
  • Alq 3 8-hydroxy-quinoline aluminum complex
  • Carbazole-based compounds dimerized styryl compounds
  • BAlq 10-hydroxybenzoquinoline-metal compound
  • Compounds of the benzoxazole, benzthiazole and benzimidazole series Compounds of the benzoxazole, benzthiazole and benzimidazole series
  • Poly(p-phenylenevinylene) (PPV) series polymer Poly(p-phenylenevinylene) (PPV) series polymer
  • Host materials for the light-emitting layer include condensed aromatic ring derivatives or heterocycle-containing 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, and ladder-type compounds. These include, but are not limited to, furan compounds and pyrimidine derivatives.
  • the light-emitting dopants include PIQIr(acac)(bis(1-phenylsoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), and PQIr(tris(1-phenylquinoline)iridium).
  • phosphorescent materials such as PtOEP (octaethylporphyrin platinum), or fluorescent materials such as Alq 3 (tris(8-hydroxyquinolino)aluminum) may be used, but are not limited to these.
  • a phosphor such as Ir(ppy) 3 (fac tris(2-phenylpyridine)iridium) or a fluorescent material such as Alq 3 (tris(8-hydroxyquinolino)aluminum) may be used as the light-emitting dopant.
  • a phosphor such as Ir(ppy) 3 (fac tris(2-phenylpyridine)iridium) or a fluorescent material such as Alq 3 (tris(8-hydroxyquinolino)aluminum) may be used as the light-emitting dopant.
  • a fluorescent material such as Alq 3 (tris(8-hydroxyquinolino)aluminum)
  • the light-emitting dopant may be a phosphorescent material such as (4,6-F2ppy) 2 Irpic, spiro-DPVBi, spiro-6P, distylbenzene (DSB), distrylarylene (DSA), Fluorescent materials such as PFO-based polymers and PPV-based polymers may be used, but are not limited to these.
  • a hole blocking layer may be provided between the electron transport layer and the light emitting layer, and materials known in the art may be used.
  • the electron transport layer may play a role in facilitating the transport of electrons.
  • the electron transport material is a material that can easily receive electrons from the cathode and transfer them to the light-emitting layer, and a material with high mobility for electrons is suitable. Specific examples include the above-mentioned compounds or Al complex of 8-hydroxyquinoline; Complex containing Alq 3 ; organic radical compounds; Hydroxyflavone-metal complexes, etc., but are not limited to these.
  • 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 in preventing the electron transport characteristics from deteriorating, and if it is 50 nm or less, the thickness of the electron transport layer is too thick to prevent the driving voltage from increasing to improve the movement of electrons. There are benefits to this.
  • the electron injection layer may serve to facilitate injection of electrons.
  • the electron injection material has the ability to transport electrons, has an excellent electron injection effect from the cathode, 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 also has an excellent electron injection effect to the light emitting layer or light emitting material.
  • Compounds with excellent thin film forming ability are preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc. and their derivatives, metals. These include, but are not limited to, complex compounds and nitrogen-containing five-membered ring derivatives.
  • metal complex compounds include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, Tris(2-methyl-8-hydroxyquinolinato)aluminum, Tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( o-cresolato) gallium, bis(2-methyl-8-quinolinato)(1-naphtolato) aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato) gallium, etc. It is not limited to this.
  • the hole blocking layer is a layer that prevents holes from reaching the cathode, and can generally be formed under the same conditions as the hole injection layer. Specifically, it includes oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complex, etc., but is not limited thereto.
  • the organic light emitting device may be a front emitting type, a back emitting type, or a double-sided emitting type depending on the material used.
  • N -([1,1',4',1''-terphenyl]-4-yl)-9,9-dimethyl-9 H -fluoren-2-amine (20.0 g, 45.70 mmol) and 6- After adding toluene (300 ml) to bromo-7-methyl-1,2,3,4-tetrahydronaphthalene (10.50 g, 46.62 mmol) and sodium tert-butoxide (5.41 g, 56.27 mmol), 10 It was heated and stirred for minutes.
  • a glass substrate coated with a thin film of ITO (Indium Tin Oxide) with a thickness of 1,400 ⁇ was placed in distilled water with a detergent dissolved in it and washed ultrasonically.
  • a detergent manufactured by Fischer Co. was used, and distilled water filtered secondarily using a filter manufactured by Millipore Co. was used as distilled water.
  • ultrasonic cleaning was repeated twice with distilled water for 10 minutes.
  • a hole injection layer was formed by thermally vacuum depositing a compound represented by the following chemical formula HAT to a thickness of 100 ⁇ .
  • a compound represented by the following chemical formula HT1 was vacuum deposited on top of the hole transport layer to a thickness of 1150 ⁇ , and then Compound 1 prepared in Synthesis Example 1 was thermally vacuum deposited to a thickness of 150 ⁇ as an electron blocking layer.
  • a compound represented by the formula BH and a compound represented by the formula BD were vacuum deposited to a thickness of 200 ⁇ at a weight ratio of 25:1.
  • a compound represented by the following chemical formula HB1 was vacuum deposited to a thickness of 50 ⁇ as a hole blocking layer.
  • a compound represented by the formula ET1 and a compound represented by LiQ below were thermally vacuum deposited at a weight ratio of 1:1 to a thickness of 310 ⁇ .
  • Lithium fluoride (LiF) to a thickness of 12 ⁇ and aluminum to a thickness of 1000 ⁇ were sequentially deposited on the electron transport and injection layer to form a cathode, thereby manufacturing an organic light-emitting device.
  • Experimental Examples 1-2 to 1-8 and Comparative Experimental Example 1-1 were conducted in the same manner as Experimental Example 1-1, except that the compounds listed in Table 1 below were used instead of Compound 1 in Experimental Example 1-1.
  • the organic light emitting devices of 1-3 to 1 were manufactured.
  • Experimental Examples and Comparisons When a current of 10 mA/cm 2 was applied to the organic light-emitting device manufactured in the experimental example, the voltage, efficiency, color coordinate, and lifespan were measured, and the results are shown in Table 1 below. Meanwhile, T95 refers to the time it takes for the luminance to decrease from the initial luminance (6000 nit) to 95%.
  • the compound of the present invention has excellent electron blocking ability, and organic light-emitting devices using it as an electron blocking layer were confirmed to exhibit significant effects in terms of driving voltage, efficiency, and lifespan.
  • the compound of the present invention has a substituent of an alkyl group having 1 to 3 carbon atoms on tetrahydronaphthalene, and the benzene ring of tetrahydronaphthalene It was confirmed that by having an alkyl or aryl group substituent in the portion, an organic light emitting device using this as an electron blocking layer has a low driving voltage, high efficiency, and long lifespan.
  • Experimental Example 1-1 except that the compound represented by the formula EB1 was used as the electron blocking layer instead of compound 1, and the compound shown in Table 2 below was used instead of the compound represented by the formula HT1 as the hole transport layer.
  • the organic light-emitting devices of Experimental Examples 2-1 to 2-14 and Comparative Experimental Examples 2-1 to 2-4 were manufactured in the same manner as Experimental Example 1-1.
  • Experimental Examples and Comparisons When a current of 10 mA/cm 2 was applied to the organic light-emitting device manufactured in the experimental example, the voltage, efficiency, color coordinate, and lifespan were measured, and the results are shown in Table 2 below. Meanwhile, T95 refers to the time it takes for the luminance to decrease from the initial luminance (6000 nit) to 95%.
  • the compound of the present invention has excellent hole transport ability, and organic light-emitting devices using it as a hole transport layer were confirmed to exhibit significant effects in terms of driving voltage, efficiency, and lifespan.
  • the compound of the present invention has a substituent of an alkyl group having 1 to 3 carbon atoms on tetrahydronaphthalene, and tetrahydronaphthalene It was confirmed that by having an alkyl or aryl group substituent on the benzene ring portion of naphthalene, an organic light emitting device using this as a hole transport layer has a low driving voltage, high efficiency, and long lifespan.

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CN113443998A (zh) * 2021-06-11 2021-09-28 长春海谱润斯科技股份有限公司 一种三芳胺类有机化合物及其有机发光器件
CN113501812A (zh) * 2021-08-12 2021-10-15 长春海谱润斯科技股份有限公司 一种三芳胺化合物及其有机电致发光器件
CN113527181A (zh) * 2021-08-12 2021-10-22 长春海谱润斯科技股份有限公司 一种含氮杂环类有机化合物及其有机发光器件
CN113735808A (zh) * 2021-09-23 2021-12-03 长春海谱润斯科技股份有限公司 一种三芳胺化合物及其有机电致发光器件

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KR101515814B1 (ko) 2012-12-13 2015-04-30 에스에프씨 주식회사 융합된 고리 치환기를 갖는 방향족 화합물 및 이를 포함하는 유기 발광 소자

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