Compound and organic light-emitting element comprising same

Abstract

The present specification relates to a compound expressed by chemical formula 1, and an organic light-emitting element comprising the compound.

Description

Compound and organic light-emitting device containing the same

[0001] The present specification relates to a compound and an organic light-emitting device comprising the same.

[0002] This application claims the benefit of the filing dates of Korean Patent Application No. 10-2024-0003408, filed with the Korean Intellectual Property Office on January 9, 2024, and Korean Patent Application No. 10-2024-0173023, filed with the Korean Intellectual Property Office on November 28, 2024, the entire contents of which are incorporated herein by reference.

[0003] In general, organic light emitting phenomenon 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 typically have a structure that includes an anode, a cathode, and an organic layer between them. Here, the organic layer is often composed of a multilayer structure composed of different materials to increase the efficiency and stability of the organic light emitting device, and can 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. In the structure of such an organic light emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet, excitons are formed, and when these excitons fall back to the ground state, light is emitted.

[0004] There is a continuing need for the development of new materials for organic light-emitting devices such as the above.

[0005] [Prior Art Literature]

[0006] (Patent Document 1) U.S. Patent Application Publication No. 2004-0251816

[0007] The present specification provides a compound and an organic light-emitting device comprising the same.

[0008] One embodiment of the present disclosure provides a compound of the following chemical formula 1.

[0009] [Chemical Formula 1]

[0010]

[0011] In the above chemical formula 1,

[0012] One or two of Y1 to Y8 are N, one of the others is C bonded to chemical formula 1, and the others are each independently CR3,

[0013] X1 is N or CR'1,

[0014] X2 is N or CR'2,

[0015] R'1 is hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; or a moiety bonded to L1, or bonded to R1 to form a substituted or unsubstituted aromatic hydrocarbon ring,

[0016] R'2 is hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; or a moiety bonded to L2, or bonded to R2 to form a substituted or unsubstituted aromatic hydrocarbon ring,

[0017] R1 and R2 are the same or different, and each independently represents a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or are combined with adjacent groups to form a substituted or unsubstituted aromatic hydrocarbon ring,

[0018] R3 is hydrogen; deuterium; or a substituted or unsubstituted alkyl group,

[0019] L1 and L2 are the same or different and each independently represent a substituted or unsubstituted arylene group,

[0020] n1 and n2 are integers from 1 to 5, respectively,

[0021] r1 and r2 are integers from 1 to 3, respectively,

[0022] If the above n1 is 2 or more, the above 2 or more L1 are equal to or different from each other,

[0023] If the above n2 is 2 or more, the above 2 or more L2 are equal to or different from each other,

[0024] If the above r1 is 2 or more, the two or more R1 are the same or different from each other,

[0025] When the above r2 is 2 or more, the two or more R2 are the same or different from each other.

[0026] In addition, one embodiment of the present specification provides an organic light-emitting device including a first electrode; a second electrode; and at least one organic layer provided between the first electrode and the second electrode, wherein at least one layer of the organic layers includes the compound.

[0027] A compound according to one embodiment of the present specification can be used as a material of an organic layer of an organic light-emitting device, and by using the compound, it is possible to improve efficiency, lower operating voltage, and / or improve lifespan characteristics in an organic light-emitting device.

[0028] Figures 1 and 2 illustrate examples of organic light-emitting devices according to one embodiment of the present specification.

[0029] [Explanation of symbols]

[0030] 101: Substrate

[0031] 102: First electrode

[0032] 111: Organic layer

[0033] 110: Second electrode

[0034] 103: Hole injection layer

[0035] 104: First hole transport layer

[0036] 105: Second hole transport layer

[0037] 106: Emissive layer

[0038] 107: Electron injection and transport layer

[0039] Hereinafter, the present specification will be described in more detail.

[0040] One embodiment of the present specification provides a compound of the above chemical formula 1.

[0041] According to an embodiment of the present disclosure, chemical formula 1 has a benzene core to which a bicyclic heterocycle containing 1 or 2 Ns is bonded, and an arylene group is necessarily included as a linking group on both sides of the benzene, and a monocyclic or bicyclic heteroaryl group containing 2 or 3 Ns is included as a substituent. Since it has an electron depletion structure, the polarity (dipole moment) of the molecule can be increased, and when manufacturing an organic light-emitting device containing the compound represented by chemical formula 1, electron mobility is smoothly controlled, and the organic light-emitting device containing the same has the effects of low voltage, high efficiency, and long life.

[0042] Throughout this specification, the term "combination thereof" included in the expressions in the Makushi format means one or more mixtures or combinations selected from the group consisting of the components described in the expressions in the Makushi format, and means including one or more selected from the group consisting of said components.

[0043] Examples of substituents in this specification are described below, but are not limited thereto.

[0044] In this specification, means the connecting part.

[0045] The term "substitution" above means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position of substitution is not limited as long as it is a position where the hydrogen atom is replaced, i.e., a position where the substituent can be replaced, and when two or more are replaced, the two or more substituents may be the same or different from each other.

[0046] The term "substituted or unsubstituted" as used herein means substituted with one or more substituents selected from the group consisting of deuterium; halogen group; cyano group; alkyl group; cycloalkyl group; alkoxy group; alkenyl group; haloalkyl group; silyl group; boron group; amine group; aryl group; and heteroaryl group, or substituted with a substituent in which two or more of the above-mentioned substituents are linked, or having no substituents.

[0047] In this specification, the connection of two or more substituents means that the hydrogen of one substituent is connected to another substituent. For example, the connection of two substituents means that a phenyl group and a naphthyl group are connected. or can be a substituent of. In addition, the connection of three substituents includes not only the case where (substituent 1)-(substituent 2)-(substituent 3) are connected sequentially, but also the case where (substituent 2) and (substituent 3) are connected to (substituent 1). For example, a phenyl group, a naphthyl group, and an isopropyl group are connected. , , or can be a substituent. The above definition also applies to cases where four or more substituents are connected.

[0048] In this specification, examples of halogen groups include a fluoro group, a chloro group, a bromo group, or an iodo group.

[0049] In the present specification, the alkyl group may be straight or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1-ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl-2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, Examples thereof include, but are not limited to, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group, isohexyl group, 2-methylpentyl group, 4-methylhexyl group, and 5-methylhexyl group.

[0050] In the present specification, the cycloalkyl group is not particularly limited, but is preferably one having 3 to 30 carbon atoms, and specifically, includes, but is not limited to, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 3-methylcyclopentyl group, a 2,3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 2,3-dimethylcyclohexyl group, a 3,4,5-trimethylcyclohexyl group, a 4-tert-butylcyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, and the like.

[0051] In the present specification, the alkoxy group may be a straight chain, branched chain, or cyclic chain. The carbon number of the alkoxy group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, it may be a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, an isobutoxy group, a tert-butoxy group, a sec-butoxy group, an n-pentyloxy group, a neopentyloxy group, an isopentyloxy group, an n-hexyloxy group, a 3,3-dimethylbutyloxy group, a 2-ethylbutyloxy group, an n-octyloxy group, an n-nonyloxy group, an n-decyloxy group, a benzyloxy group, a p-methylbenzyloxy group, etc., but is not limited thereto.

[0052] In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples include, but are not limited to, a vinyl group, a 1-propenyl group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 3-methyl-1-butenyl group, a 1,3-butadienyl group, an allyl group, a 1-phenylvinyl-1-yl group, a 2-phenylvinyl-1-yl group, a 2,2-diphenylvinyl-1-yl group, a 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl group, a 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, a stilbenyl group, and a styrenyl group.

[0053] In this specification, the haloalkyl group means that at least one halogen group is substituted for hydrogen in the alkyl group among the definitions of the alkyl group.

[0054] In the present specification, the aryl group is not particularly limited, but is preferably one having 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.

[0055] When the above aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30 carbon atoms. Specifically, the monocyclic aryl group may include, but is not limited to, a phenyl group, a biphenyl group, a terphenyl group, etc.

[0056] When the above aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 10 to 30 carbon atoms. Specifically, the polycyclic aryl group may include, but is not limited to, a naphthyl group, anthracene group, phenanthrene group, triphenylene group, pyrene group, phenalene group, perylene group, chrysene group, fluorene group, etc.

[0057] In the present specification, the fluorene group may be substituted, and adjacent groups may be combined with each other to form a ring.

[0058] When the above fluorene group is substituted, There are, but are not limited to, the following.

[0059] In this specification, the term "adjacent" may refer to a substituent substituted on an atom directly connected to the atom substituted by the substituent, a substituent that is sterically closest to the substituent, or another substituent substituted on the atom substituted by the substituent. For example, two substituents substituted at ortho positions in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring may be interpreted as "adjacent" groups.

[0060] In the present specification, a heteroaryl group includes one or more non-carbon atoms or heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, P, Si, and S. The number of carbon atoms in the heteroaryl group is not particularly limited, but is preferably 2 to 30 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic. Examples of heteroaryl groups include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, pyridine group, bipyridine group, pyrimidine group, triazine group, triazole group, acridine group, pyridazine group, pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, pyridopyrimidine group, pyridopyrazine group, pyrazinopyrazine group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuran group, phenanthridine, phenanthroline, isoxazole group, thiadiazole group, Examples thereof include, but are not limited to, dibenzofuran group, dibenzosilole group, phenoxathiine group, phenoxazine group, phenothiazine group, dihydroindenocarbazole group, spirofluorenxanthene group, and spirofluorenethioxanthene group.

[0061] In the present specification, the silyl group may be an alkylsilyl group, an arylsilyl group, a heteroarylsilyl group, etc. Among the alkylsilyl groups, the alkyl group may be applied with the examples of the alkyl group described above, among the arylsilyl groups, the aryl group may be applied with the examples of the aryl group described above, and among the heteroarylsilyl groups, the heteroaryl group may be applied with the examples of the heterocyclic group described above.

[0062] In this specification, the boron group is -BG 100 G 101 It may be, and the above G 100 and G 101are the same or different, and each independently hydrogen; deuterium; halogen; a nitrile group; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms. The boron group is specifically, but is not limited to, a dimethyl boron group, a diethyl boron group, a t-butylmethyl boron group, a diphenyl boron group, etc.

[0063] In the present specification, the amine group may be selected from the group consisting of -NH2, an alkylamine group, an N-alkylarylamine group, an arylamine group, an N-arylheteroarylamine group, an N-alkylheteroarylamine group, and a heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, anthracenylamine group, a 9-methyl-anthracenylamine group, a diphenylamine group, a ditolylamine group, an N-phenyltolylamine group, an N-phenylbiphenylamine group, an N-phenylnaphthylamine group, an N-biphenylnaphthylamine group; Examples thereof include, but are not limited to, N-naphthylfluorenylamine group, N-phenylphenanthrenylamine group, N-biphenylphenanthrenylamine group, N-phenylfluorenylamine group, N-phenylterphenylamine group, N-phenanthrenylfluorenylamine group, N-biphenylfluorenylamine group, etc.

[0064] In this specification, an N-alkylarylamine group means an amine group in which an alkyl group and an aryl group are substituted on N of the amine group. The alkyl group and aryl group in the N-alkylarylamine group are the same as the examples of the alkyl group and aryl group described above.

[0065] In this specification, an N-arylheteroarylamine group refers to an amine group in which an aryl group and a heteroaryl group are substituted on the N of the amine group. The aryl group and heteroaryl group in the N-arylheteroarylamine group are the same as the examples of the aryl group and heteroaryl group described above.

[0066] In this specification, an N-alkylheteroarylamine group means an amine group in which an alkyl group and a heteroaryl group are substituted for N of the amine group. The alkyl group and heteroaryl group in the N-alkylheteroarylamine group are the same as the examples of the alkyl group and heteroaryl group described above.

[0067] In the present specification, examples of arylamine groups include substituted or unsubstituted monoarylamine groups, or substituted or unsubstituted diarylamine groups. The arylamine group including two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or both a monocyclic aryl group and a polycyclic aryl group. For example, the aryl group in the arylamine group may be selected from the examples of the aryl groups described above.

[0068] In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, or a substituted or unsubstituted diheteroarylamine group. The heteroarylamine group including two or more heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or both a monocyclic heteroaryl group and a polycyclic heteroaryl group. For example, the heteroaryl group in the heteroarylamine group may be selected from the examples of the above-mentioned heteroaryl groups.

[0069] In the present specification, the alkyl group among the alkylthioxy group and the alkylsulfoxy group is the same as the examples of the alkyl group described above. Specifically, the alkylthioxy group includes a methylthioxy group, an ethylthioxy group, a tert-butylthioxy group, a hexylthioxy group, an octylthioxy group, etc., and the alkylsulfoxy group includes a methylsulfoxy group, an ethylsulfoxy group, a propylsulfoxy group, a butylsulfoxy group, etc., but is not limited thereto.

[0070] In this specification, the phosphine oxide group specifically includes an alkylphosphine oxide group, an arylphosphine oxide group, etc., and more specifically includes a diphenylphosphine oxide group, a dinaphthylphosphine oxide group, etc., but is not limited thereto.

[0071] In this specification, the aryl group among the aryloxy group, arylthioxy group, arylsulfoxy group, and arylphosphine group is the same as the examples of the aryl group described above. Specifically, examples of the aryloxy group include a phenoxy group, a p-toryloxy group, a m-toryloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6-trimethylphenoxy group, a p-tert-butylphenoxy group, a 3-biphenyloxy group, a 4-biphenyloxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 4-methyl-1-naphthyloxy group, a 5-methyl-2-naphthyloxy group, a 1-anthryloxy group, a 2-anthryloxy group, a 9-anthryloxy group, a 1-phenanthryloxy group, a 3-phenanthryloxy group, a 9-phenanthryloxy group, etc., examples of the arylthioxy group include a phenylthioxy group, a 2-methylphenylthioxy group, a 4-tert-butylphenylthioxy group, etc., examples of the arylsulfoxy group include a benzenesulfoxy group, a p-toluenesulfoxy group, etc., but are not limited thereto.

[0072] In this specification, the term “adjacent groups combine with each other to form a ring” among substituents means that adjacent groups combine with each other to form a substituted or unsubstituted hydrocarbon ring; or a substituted or unsubstituted heterocycle.

[0073] In the present specification, in a substituted or unsubstituted ring formed by combining with each other, “ring” means a substituted or unsubstituted hydrocarbon ring; or a substituted or unsubstituted heterocycle.

[0074] In the present specification, the hydrocarbon ring may be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a condensed ring of an aromatic hydrocarbon and an aliphatic hydrocarbon, and may be selected from among the examples of the cycloalkyl group or aryl group, except for the non-monovalent ones.

[0075] In the present specification, a heterocycle includes one or more non-carbon atoms or heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S. The heterocycle may be monocyclic or polycyclic, and may be an aromatic, aliphatic, or a condensed ring of aromatic and aliphatic groups, and the aromatic heterocycle may be selected from examples of the heteroaryl group, except that it is not monovalent.

[0076] In the present specification, an aliphatic heterocycle means an aliphatic ring containing at least one heteroatom. Examples of aliphatic heterocycles include, but are not limited to, oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, azocane, and thiocane.

[0077] In this specification, an arylene group means a divalent group having two bonding positions to an aryl group. The description of the aryl group described above may be applied to these groups, except that each is a divalent group.

[0078] Unless otherwise defined herein, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. Although methods and materials similar or equivalent to those described herein can be used in the practice or testing of embodiments of the present invention, suitable methods and materials are described below. All publications, patent applications, patents, and other references mentioned herein are incorporated by reference in their entirety, and in case of conflict, this specification, including definitions, will control unless a specific passage is cited. Furthermore, the materials, methods, and examples are illustrative only and not intended to be limiting.

[0079] Hereinafter, the compound represented by the chemical formula 1 will be described in detail.

[0080] According to one embodiment of the present specification, the chemical formula 1 is any one of the following chemical formulas 1-1 to 1-6.

[0081] [Chemical Formula 1-1]

[0082]

[0083] [Chemical Formula 1-2]

[0084]

[0085] [Chemical Formula 1-3]

[0086]

[0087] [Chemical Formula 1-4]

[0088]

[0089] [Chemical Formula 1-5]

[0090]

[0091] [Chemical Formula 1-6]

[0092]

[0093] In the above chemical formulas 1-1 to 1-6,

[0094] The definitions of Y1 to Y8, X1, X2, R1, R2, r1, r2, L1, L2, n1 and n2 are the same as those defined in the above chemical formula 1.

[0095] According to one embodiment of the present specification, the chemical formula 1 is the following chemical formula 1-7 or 1-8.

[0096] [Chemical Formula 1-7]

[0097]

[0098] [Chemical Formula 1-8]

[0099]

[0100] In the above chemical formulas 1-7 and 1-8,

[0101] The definitions of Y1 to Y8, X1, X2, R1, R2, r1, r2, L1, L2, n1 and n2 are the same as those defined in the above chemical formula 1.

[0102] According to one embodiment of the present specification, Y8 is C bonded to chemical formula 1, Y1 is N, and Y2 to Y7 are each independently CR3.

[0103] According to one embodiment of the present specification, Y8 is C bonded to chemical formula 1, Y2 is N, and Y1 and Y3 to Y7 are each independently CR3.

[0104] According to one embodiment of the present specification, Y8 is C bonded to chemical formula 1, Y3 is N, and Y1, Y2 and Y4 to Y7 are each independently CR3.

[0105] According to one embodiment of the present specification, Y8 is C bonded to chemical formula 1, Y4 is N, and Y1 to Y3 and Y5 to Y7 are each independently CR3.

[0106] According to one embodiment of the present specification, Y8 is C bonded to chemical formula 1, Y5 is N, and Y1 to Y4, Y6 and Y7 are each independently CR3.

[0107] According to one embodiment of the present specification, Y8 is C bonded to chemical formula 1, Y6 is N, and Y1 to Y5 and Y7 are each independently CR3.

[0108] According to one embodiment of the present specification, Y8 is C bonded to chemical formula 1, Y7 is N, and Y1 to Y6 are each independently CR3.

[0109] According to one embodiment of the present specification, Y8 is C bonded to chemical formula 1, Y1 and Y2 are N, and Y3 to Y7 are each independently CR3.

[0110] According to one embodiment of the present specification, Y8 is C bonded to chemical formula 1, Y1 and Y3 are N, and Y2 and Y4 to Y7 are each independently CR3.

[0111] According to one embodiment of the present specification, Y8 is C bonded to chemical formula 1, Y1 and Y4 are N, and Y2, Y3 and Y5 to Y7 are each independently CR3.

[0112] According to one embodiment of the present specification, Y8 is C bonded to chemical formula 1, Y1 and Y5 are N, and Y2 to Y4, Y6 and Y7 are each independently CR3.

[0113] According to one embodiment of the present specification, Y8 is C bonded to chemical formula 1, Y1 and Y6 are N, and Y2 to Y5 and Y7 are each independently CR3.

[0114] According to one embodiment of the present specification, Y8 is C bonded to chemical formula 1, Y1 and Y7 are N, and Y2 to Y6 are each independently CR3.

[0115] According to one embodiment of the present specification, Y8 is C bonded to chemical formula 1, Y2 and Y3 are N, and Y1 and Y4 to Y7 are each independently CR3.

[0116] According to one embodiment of the present specification, Y8 is C bonded to chemical formula 1, Y2 and Y4 are N, and Y1, Y3 and Y5 to Y7 are each independently CR3.

[0117] According to one embodiment of the present specification, Y8 is C bonded to chemical formula 1, Y2 and Y5 are N, and Y1, Y3, Y4, Y6 and Y7 are each independently CR3.

[0118] According to one embodiment of the present specification, Y8 is C bonded to chemical formula 1, Y2 and Y6 are N, and Y1, Y3 to Y5 and Y7 are each independently CR3.

[0119] According to one embodiment of the present specification, Y8 is C bonded to chemical formula 1, Y2 and Y7 are N, and Y1 and Y3 to Y6 are each independently CR3.

[0120] According to one embodiment of the present specification, Y8 is C bonded to chemical formula 1, Y3 and Y4 are N, and Y1, Y2 and Y5 to Y7 are each independently CR3.

[0121] According to one embodiment of the present specification, Y8 is C bonded to chemical formula 1, Y3 and Y5 are N, and Y1, Y2, Y4, Y6 and Y7 are each independently CR3.

[0122] According to one embodiment of the present specification, Y8 is C bonded to chemical formula 1, Y3 and Y6 are N, and Y1, Y2, Y4, Y5 and Y7 are each independently CR3.

[0123] According to one embodiment of the present specification, Y8 is C bonded to chemical formula 1, Y3 and Y7 are N, and Y1, Y2 and Y4 to Y6 are each independently CR3.

[0124] According to one embodiment of the present specification, Y8 is C bonded to chemical formula 1, Y4 and Y5 are N, and Y1 to Y3, Y6 and Y7 are each independently CR3.

[0125] According to one embodiment of the present specification, Y8 is C bonded to chemical formula 1, Y4 and Y6 are N, and Y1 to Y3, Y5 and Y7 are each independently CR3.

[0126] According to one embodiment of the present specification, Y8 is C bonded to chemical formula 1, Y4 and Y7 are N, and Y1 to Y3, Y5 and Y6 are each independently CR3.

[0127] According to one embodiment of the present specification, Y8 is C bonded to chemical formula 1, Y5 and Y6 are N, and Y1 to Y4, Y6 and Y7 are each independently CR3.

[0128] According to one embodiment of the present specification, Y8 is C bonded to chemical formula 1, Y5 and Y7 are N, and Y1 to Y4 and Y6 are each independently CR3.

[0129] According to one embodiment of the present specification, Y8 is C bonded to chemical formula 1, Y6 and Y7 are N, and Y1 to Y5 are each independently CR3.

[0130] According to one embodiment of the present specification, Y1 is C bonded to chemical formula 1, Y2 is N, and Y3 to Y8 are each independently CR3.

[0131] According to one embodiment of the present specification, Y1 is C bonded to chemical formula 1, Y3 is N, and Y2 and Y4 to Y8 are each independently CR3.

[0132] According to one embodiment of the present specification, Y1 is C bonded to chemical formula 1, Y4 is N, and Y2, Y3 and Y5 to Y8 are each independently CR3.

[0133] According to one embodiment of the present specification, Y1 is C bonded to chemical formula 1, Y5 is N, and Y2 to Y4 and Y6 to Y8 are each independently CR3.

[0134] According to one embodiment of the present specification, Y1 is C bonded to chemical formula 1, Y6 is N, and Y2 to Y5, Y7 and Y8 are each independently CR3.

[0135] According to one embodiment of the present specification, Y1 is C bonded to chemical formula 1, Y7 is N, and Y2 to Y6 and Y8 are each independently CR3.

[0136] According to one embodiment of the present specification, Y1 is C bonded to chemical formula 1, Y8 is N, and Y2 to Y7 are each independently CR3.

[0137] According to one embodiment of the present specification, Y1 is C bonded to chemical formula 1, Y2 and Y3 are N, and Y4 to Y8 are each independently CR3.

[0138] According to one embodiment of the present specification, Y1 is C bonded to chemical formula 1, Y2 and Y4 are N, and Y3 and Y5 to Y8 are each independently CR3.

[0139] According to one embodiment of the present specification, Y1 is C bonded to chemical formula 1, Y2 and Y5 are N, and Y3, Y4 and Y6 to Y8 are each independently CR3.

[0140] According to one embodiment of the present specification, Y1 is C bonded to chemical formula 1, Y2 and Y6 are N, and Y3 to Y5, Y7 and Y8 are each independently CR3.

[0141] According to one embodiment of the present specification, Y1 is C bonded to chemical formula 1, Y2 and Y7 are N, and Y3 to Y6 and Y8 are each independently CR3.

[0142] According to one embodiment of the present specification, Y1 is C bonded to chemical formula 1, Y2 and Y8 are N, and Y3 to Y7 are each independently CR3.

[0143] According to one embodiment of the present specification, Y1 is C bonded to chemical formula 1, Y3 and Y4 are N, and Y2 and Y5 to Y8 are each independently CR3.

[0144] According to one embodiment of the present specification, Y1 is C bonded to chemical formula 1, Y3 and Y5 are N, and Y2, Y4 and Y6 to Y8 are each independently CR3.

[0145] According to one embodiment of the present specification, Y1 is C bonded to chemical formula 1, Y3 and Y6 are N, and Y2, Y4, Y5, Y7 and Y8 are each independently CR3.

[0146] According to one embodiment of the present specification, Y1 is C bonded to chemical formula 1, Y3 and Y7 are N, and Y2, Y4 to Y6 and Y8 are each independently CR3.

[0147] According to one embodiment of the present specification, Y1 is C bonded to chemical formula 1, Y3 and Y8 are N, and Y2 and Y4 to Y7 are each independently CR3.

[0148] According to one embodiment of the present specification, Y1 is C bonded to chemical formula 1, Y4 and Y5 are N, and Y2, Y3 and Y6 to Y8 are each independently CR3.

[0149] According to one embodiment of the present specification, Y1 is C bonded to chemical formula 1, Y6 and Y6 are N, and Y1, Y2, Y3, Y5 and Y7 are each independently CR3.

[0150] According to one embodiment of the present specification, Y1 is C bonded to chemical formula 1, Y4 and Y7 are N, and Y2, Y3, Y5, Y6 and Y8 are each independently CR3.

[0151] According to one embodiment of the present specification, Y1 is C bonded to chemical formula 1, Y4 and Y8 are N, and Y2, Y3 and Y5 to Y7 are each independently CR3.

[0152] According to one embodiment of the present specification, Y1 is C bonded to chemical formula 1, Y5 and Y6 are N, and Y2 to Y4, Y7 and Y8 are each independently CR3.

[0153] According to one embodiment of the present specification, Y1 is C bonded to chemical formula 1, Y5 and Y7 are N, and Y2 to Y5, Y6 and Y8 are each independently CR3.

[0154] According to one embodiment of the present specification, Y1 is C bonded to chemical formula 1, Y5 and Y8 are N, and Y2 to Y4, Y6 and Y7 are each independently CR3.

[0155] According to one embodiment of the present specification, Y1 is C bonded to chemical formula 1, Y6 and Y7 are N, and Y2 to Y5, Y7 and Y8 are each independently CR3.

[0156] According to one embodiment of the present specification, Y1 is C bonded to chemical formula 1, Y6 and Y8 are N, and Y2 to Y5 and Y7 are each independently CR3.

[0157] According to one embodiment of the present specification, Y1 is C bonded to chemical formula 1, Y7 and Y8 are N, and Y2 to Y6 are each independently CR3.

[0158] According to one embodiment of the present specification, the chemical formula 1 is one of the following structural formulas.

[0159]

[0160]

[0161] In the above structure,

[0162] * is a site that is bonded to the above chemical formula 1,

[0163] R31 to R38 are the same or different, and each independently represent hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

[0164] According to one embodiment of the present specification, X1 is N or CR'1.

[0165] According to another embodiment of the present specification, R'1 is hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0166] According to another embodiment of the present specification, R'1 is hydrogen.

[0167] According to another embodiment of the present specification, R'1 is a moiety bonded to L1.

[0168] According to another embodiment of the present specification, R'1 is combined with R1 to form a substituted or unsubstituted aromatic hydrocarbon ring.

[0169] According to another embodiment of the present specification, R'1 is combined with R1 to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 2 to 30 carbon atoms.

[0170] According to another embodiment of the present specification, R'1 combines with R1 to form a substituted or unsubstituted benzene.

[0171] According to one embodiment of the present specification, X2 is N or CR'1.

[0172] According to another embodiment of the present specification, R'2 is hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0173] According to another embodiment of the present specification, R'2 is hydrogen.

[0174] According to another embodiment of the present specification, R'2 is a moiety bonded to L2.

[0175] According to another embodiment of the present specification, R'2 is combined with R2 to form a substituted or unsubstituted aromatic hydrocarbon ring.

[0176] According to another embodiment of the present specification, R'2 is combined with R2 to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 2 to 30 carbon atoms.

[0177] According to another embodiment of the present specification, R'2 combines with R2 to form a substituted or unsubstituted benzene.

[0178] According to one embodiment of the present specification, n1 is 1.

[0179] According to one embodiment of the present specification, n1 is 2.

[0180] According to one embodiment of the present specification, n1 is 3.

[0181] In the chemical formula 1 herein, when n1 is 2 or more, it means that two or more L1s are the same or different from each other, and each L1 is connected in series. For example, when n1 is 3 and L1s are each a phenylene group, a naphthylene group, and a phenylene group, they can be connected as follows, but are not limited thereto, and the order or connection position of each L1 may be different.

[0182]

[0183] Also, the above For example, when n1 is 3, it means that it is bonded to the substituent at the third terminal position in the above-mentioned structure, that is, the phenylene group, and * means a site that is bonded to the above-mentioned chemical formula 1, refers to a site that is bound to the terminal of the above L1.

[0184] The above description of n1 also applies equally to the description of n2.

[0185] According to one embodiment of the present specification, n2 is 1.

[0186] According to one embodiment of the present specification, n2 is 2.

[0187] According to one embodiment of the present specification, n2 is 3.

[0188] According to one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently represents a substituted or unsubstituted arylene group.

[0189] According to one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0190] According to one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

[0191] According to one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 10 carbon atoms.

[0192] According to one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently is an arylene group.

[0193] According to one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently represents a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0194] According to one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently represents a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

[0195] According to one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently represents a monocyclic or polycyclic arylene group having 6 to 10 carbon atoms.

[0196] According to one embodiment of the present specification, L1 and L2 are phenylene groups.

[0197] According to one embodiment of the present specification, L1, L2, and Two of them are located in the ortho orientation.

[0198] According to one embodiment of the present specification, the chemical formula 1 is the following chemical formula 2.

[0199] [Chemical Formula 2]

[0200]

[0201] In the above chemical formula 2,

[0202] The definitions of Y1 to Y8, X1, X2, R1, R2, r1 and r2 are the same as those defined in the above chemical formula 1.

[0203] In one embodiment of the present specification, phenylene (ring 2 and ring 3 below) connected to the central phenyl group (ring 1 below) in the chemical formula 2, and Two of them are positioned in an ortho orientation from the central phenyl group (ring 1 below).

[0204]

[0205] According to one embodiment of the present specification, the chemical formula 1 is one of the structures selected from the following.

[0206]

[0207] In the above structure,

[0208] * is the site that binds to chemical formula 1,

[0209] The definitions of L1, n1, R1, r1 and R'1 are the same as those defined in the above chemical formula 1,

[0210] R101 is hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

[0211] r101 is an integer from 1 to 4,

[0212] When the above r101 is 2 or more, the above 2 or more R101 are the same or different from each other.

[0213] According to one embodiment of the present specification, the chemical formula 1 is one of the structures selected from the following.

[0214]

[0215] In the above structure,

[0216] * is the site that binds to chemical formula 1,

[0217] The definitions of L2, n2, R2, r2 and R'2 are the same as those defined in the above chemical formula 1,

[0218] R201 is hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

[0219] R201 is an integer from 1 to 4,

[0220] When the above r201 is 2 or more, the above 2 or more R201 are the same or different from each other.

[0221] According to one embodiment of the present specification, the chemical formula 1 and are identical to each other.

[0222] According to one embodiment of the present specification, the chemical formula 1 and They are different from each other.

[0223] According to one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently represent a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, which is substituted or unsubstituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, which is substituted or unsubstituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, which is substituted or unsubstituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic heteroaryl group having 6 to 30 carbon atoms,

[0224] The above R'1 is hydrogen; deuterium; a straight or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a moiety bonded to L1,

[0225] The above R'2 is hydrogen; deuterium; a straight or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a moiety bonded to L2,

[0226] The above L1 and L2 are the same or different, and each independently represents a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms,

[0227] The above R3 is hydrogen; deuterium; or a straight or branched chain alkyl group having 1 to 30 carbon atoms.

[0228] According to one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0229] According to one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

[0230] According to one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms.

[0231] According to one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently represent a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, which is unsubstituted or substituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, which is unsubstituted or substituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, which is unsubstituted or substituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic heteroaryl group having 6 to 30 carbon atoms.

[0232] According to one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently represent a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, which is unsubstituted or substituted with a straight-chain or branched-chain alkyl group having 1 to 20 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 20 carbon atoms, or a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms, which is unsubstituted or substituted with a straight-chain or branched-chain alkyl group having 1 to 20 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms, which is unsubstituted or substituted with a straight-chain or branched-chain alkyl group having 1 to 20 carbon atoms, or a monocyclic or polycyclic heteroaryl group having 6 to 20 carbon atoms.

[0233] According to one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently represent a phenyl group unsubstituted or substituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms substituted or unsubstituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; a biphenyl group; a naphthyl group; or a pyridine group unsubstituted or substituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0234] According to one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently represent a phenyl group unsubstituted or substituted with a straight-chain or branched-chain alkyl group having 1 to 20 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 20 carbon atoms, or a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms substituted or unsubstituted with a straight-chain or branched-chain alkyl group having 1 to 20 carbon atoms; a biphenyl group; a naphthyl group; or a pyridine group unsubstituted or substituted with a straight-chain or branched-chain alkyl group having 1 to 20 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0235] According to one embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently a phenyl group unsubstituted or substituted with a methyl group, a tert-butyl group, a cyclohexyl group, or a pyridine group unsubstituted or substituted with a methyl group; a biphenyl group; a naphthyl group; or a pyridine group unsubstituted or substituted with a methyl group or a phenyl group.

[0236] According to one embodiment of the present specification, one of the R1s is a moiety bonded to L1, and the remaining R1s are the aforementioned substituents.

[0237] According to one embodiment of the present specification, one of the R2s is a moiety bonded to L2, and the remaining R2s are the aforementioned substituents.

[0238] According to one embodiment of the present specification, R3 is hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

[0239] According to one embodiment of the present specification, R3 is hydrogen; deuterium; or a substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms.

[0240] According to one embodiment of the present specification, R3 is hydrogen; deuterium; or a substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to 20 carbon atoms.

[0241] According to one embodiment of the present specification, R3 is hydrogen; deuterium; or a substituted or unsubstituted straight or branched chain alkyl group having 1 to 10 carbon atoms.

[0242] According to one embodiment of the present specification, R3 is hydrogen; deuterium; or an alkyl group.

[0243] According to one embodiment of the present specification, R3 is hydrogen; deuterium; or a straight or branched chain alkyl group having 1 to 30 carbon atoms.

[0244] According to one embodiment of the present specification, R3 is hydrogen; deuterium; or a straight or branched chain alkyl group having 1 to 20 carbon atoms.

[0245] According to one embodiment of the present specification, R3 is hydrogen; deuterium; or a straight or branched chain alkyl group having 1 to 10 carbon atoms.

[0246] According to one embodiment of the present specification, R3 is hydrogen; deuterium; or a methyl group.

[0247] According to one embodiment of the present specification, one of the R3s is a moiety bonded to the phenyl group (benzene ring) of chemical formula 1, and the remaining R3s are the aforementioned substituents.

[0248] According to one embodiment of the present specification, R31 to R38 are the same as or different from each other, and each independently represents hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

[0249] According to one embodiment of the present specification, R31 to R38 are the same as or different from each other, and each independently represent hydrogen; deuterium; or a substituted or unsubstituted straight or branched chain alkyl group having 1 to 30 carbon atoms.

[0250] According to one embodiment of the present specification, R31 to R38 are the same as or different from each other, and each independently represent hydrogen; deuterium; or a substituted or unsubstituted straight or branched chain alkyl group having 1 to 20 carbon atoms.

[0251] According to one embodiment of the present specification, R31 to R38 are the same as or different from each other, and each independently represent hydrogen; deuterium; or a substituted or unsubstituted straight or branched chain alkyl group having 1 to 10 carbon atoms.

[0252] According to one embodiment of the present specification, R31 to R38 are the same as or different from each other, and are each independently hydrogen; deuterium; or an alkyl group.

[0253] According to one embodiment of the present specification, R31 to R38 are the same as or different from each other, and each independently represent hydrogen; deuterium; or a straight or branched alkyl group having 1 to 30 carbon atoms.

[0254] According to one embodiment of the present specification, R31 to R38 are the same as or different from each other, and each independently represent hydrogen; deuterium; or a straight or branched alkyl group having 1 to 20 carbon atoms.

[0255] According to one embodiment of the present specification, R31 to R38 are the same as or different from each other, and each independently represent hydrogen; deuterium; or a straight or branched alkyl group having 1 to 10 carbon atoms.

[0256] According to one embodiment of the present specification, R31 to R38 are the same as or different from each other, and are each independently hydrogen; deuterium; or a methyl group.

[0257] According to one embodiment of the present specification, the chemical formula 1 is any one of the following compounds.

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283] One embodiment of the present specification provides an organic light-emitting device comprising a compound represented by the chemical formula 1.

[0284] When it is said in this specification that a member is located "on" another member, this includes not only cases where the member is in contact with the other member, but also cases where another member exists between the two members.

[0285] When a part in this specification is said to "include" a certain component, this does not mean that it excludes other components, but rather that it may include other components, unless otherwise specifically stated.

[0286] In this specification, the term "layer" is interchangeable with the term "film", which is commonly used in the present technical field, and refers to a coating covering a target area. The size of the "layer" is not limited, and each "layer" may have the same or different sizes. According to one embodiment, the size of the "layer" may be the same as the entire device, may correspond to the size of a specific functional area, or may be as small as a single sub-pixel.

[0287] In this specification, the meaning of a specific A material being included in a B layer includes both i) one or more A materials being included in one B layer and ii) the B layer being composed of one or more layers and the A material being included in one or more layers of the multiple B layers.

[0288] In this specification, the meaning that a specific A material is included in a C layer or a D layer means that i) it is included in at least one layer among at least one C layer, ii) it is included in at least one layer among at least one D layer, or iii) it is included in at least one C layer and at least one D layer, respectively.

[0289] The present specification provides an organic light-emitting device comprising a first electrode; a second electrode; and at least one organic layer provided between the first electrode and the second electrode, wherein at least one of the organic layers comprises a compound represented by the chemical formula 1.

[0290] The organic layer of the organic light-emitting device of the present specification may be formed as a single-layer structure, but may also be formed as a multi-layer structure in which two or more organic layers are laminated. For example, it may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, etc. However, the structure of the organic light-emitting device is not limited thereto and may include a smaller number of organic layers.

[0291] According to one embodiment of the present specification, the organic layer includes an electron transport region between the light-emitting layer and the second electrode, and the electron transport region includes the compound. The electron transport region may include at least one of an electron injection layer, an electron transport layer, an electron injection and transport layer, and a hole blocking layer.

[0292] According to one embodiment of the present specification, the organic layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, electron transport layer, or electron injection and transport layer includes the compound.

[0293] According to one embodiment of the present specification, the organic layer includes a hole blocking layer, and the hole blocking layer includes the compound.

[0294] According to one embodiment of the present specification, the electron transport region further includes, in addition to the compound of the chemical formula 1, one or more n-type dopants selected from alkali metals and alkaline earth metals.

[0295] When an organic alkali metal compound or an organic alkaline earth metal compound is used as an n-type dopant, stability against holes from the light-emitting layer can be secured, thereby improving the lifespan of the organic light-emitting device. In addition, the electron mobility of the electron transport layer can be increased by controlling the ratio of the organic alkali metal compound or the organic alkaline earth metal compound, thereby maximizing the balance of holes and electrons in the light-emitting layer, thereby increasing light emission efficiency.

[0296] According to one embodiment of the present specification, the n-type dopant is 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, Examples thereof include, but are not limited to, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc. In one embodiment, LiQ is more preferred as the n-type dopant.

[0297] According to one embodiment of the present specification, the electron transport region includes the compound of the chemical formula 1 and an n-type dopant in the same organic layer. Alternatively, the electron transport region includes two or more adjacent organic layers, and each organic layer may be formed only of the compound of the chemical formula 1 or an n-type dopant.

[0298] According to one embodiment of the present specification, the electron transport region may include a compound of chemical formula 1 and an n-type dopant in a weight ratio of 2:8 to 8:2, preferably 3:7 to 7:3, and more preferably 4:6 to 6:4.

[0299] According to one embodiment of the present specification, the organic layer includes a light-emitting layer.

[0300] According to one embodiment of the present specification, the organic layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer.

[0301] According to one embodiment of the present specification, the organic layer includes an electron blocking layer.

[0302] According to one embodiment of the present specification, the organic layer includes a hole blocking layer.

[0303] According to one embodiment of the present specification, the organic light-emitting device further includes one or two or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a hole injection and transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, a hole blocking layer, and an electron blocking layer.

[0304] According to one embodiment of the present specification, the organic light-emitting element includes a first electrode; a second electrode provided opposite the first electrode; a light-emitting layer provided between the first electrode and the second electrode; and two or more organic layers provided between the light-emitting layer and the first electrode, or between the light-emitting layer and the second electrode.

[0305] According to one embodiment of the present specification, the two or more organic layers may be selected from the group consisting of a hole injection layer, a hole transport layer, a hole injection and transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, a hole blocking layer, and an electron blocking layer.

[0306] According to one embodiment of the present specification, two or more hole transport layers are included between the light-emitting layer and the first electrode. The two or more hole transport layers may include materials that are the same or different from each other.

[0307] According to one embodiment of the present specification, the first electrode is an anode or a cathode.

[0308] According to one embodiment of the present specification, the second electrode is a cathode or an anode.

[0309] According to one embodiment of the present specification, the organic light-emitting device may be an organic light-emitting device having a structure (normal type) in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate.

[0310] According to one embodiment of the present specification, the organic light-emitting device may be an inverted type organic light-emitting device in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate.

[0311] For example, the structure of an organic light-emitting device according to one embodiment of the present specification is illustrated in FIGS. 1 and 2. FIGS. 1 and 2 illustrate the organic light-emitting device and are not limited thereto.

[0312] Figure 1 illustrates the structure of an organic light-emitting device in which a first electrode (102), an organic layer (111), and a second electrode (110) are sequentially laminated on a substrate (101). The compound represented by the chemical formula 1 is included in the organic layer.

[0313] FIG. 2 illustrates the structure of an organic light-emitting device in which a first electrode (102), a hole injection layer (103), a first hole transport layer (104), a second hole transport layer (105), a light-emitting layer (106), an electron injection and transport layer (107), and a second electrode (110) are sequentially laminated on a substrate (101). The compound represented by the above chemical formula 1 is included in the electron injection and transport layer.

[0314] The organic light-emitting device of the present specification can be manufactured using materials and methods known in the art, except that the electron injection layer, electron transport layer, electron injection and transport layer, or hole blocking layer includes the compound, i.e., the compound represented by the chemical formula 1.

[0315] When the organic light-emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.

[0316] For example, the organic light-emitting device of the present specification can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. At this time, a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation is used to deposit a metal or a conductive metal oxide or an alloy thereof on the substrate to form an anode, and then an organic layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer is formed thereon, and then a material that can be used as a cathode is deposited thereon. In addition to this method, the organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on the substrate.

[0317] In addition, the compound represented by the above chemical formula 1 can be formed into an organic layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light-emitting device. Here, the solution coating method refers to, but is not limited to, spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc.

[0318] In addition to this method, an organic light-emitting device can also be manufactured by sequentially depositing an organic layer, an anode material, and a cathode material on a substrate. However, the manufacturing method is not limited to this.

[0319] The anode material is preferably a material having a high work function to facilitate hole injection into the organic layer. Examples thereof include, but are not limited to, 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); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

[0320] The cathode material is preferably a material with a low work function to facilitate electron injection into the organic layer. Examples thereof include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayered materials such as LiF / Al or LiO2 / Al.

[0321] The above-described light-emitting layer may include a host material and a dopant material. The host material may include a condensed aromatic ring derivative or a heterocyclic compound. Specifically, the condensed aromatic ring derivative may include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and the heterocyclic compound may include, but is not limited to, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc.

[0322] According to one embodiment of the present specification, the host includes, but is not limited to, a compound represented by the following chemical formula H-1.

[0323] [Chemical Formula H-1]

[0324]

[0325] In the above chemical formula H-1,

[0326] L20 and L21 are the same or different from each other, and each independently represents a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group,

[0327] Ar20 and Ar21 are the same or different, and each independently represent hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

[0328] R201 is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

[0329] r201 is an integer from 1 to 8, and when r201 is 2 or more, 2 or more R201 are the same as or different from each other.

[0330] In one embodiment of the present specification, L20 and L21 are the same as or different from each other, and each independently represents a direct bond; a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; or a monocyclic or polycyclic divalent heterocyclic group having 2 to 30 carbon atoms.

[0331] In one embodiment of the present specification, L20 and L21 are the same as or different from each other, and each independently represent a direct bond; a phenylene group substituted or unsubstituted with deuterium; a biphenylylene group substituted or unsubstituted with deuterium; a naphthylene group substituted or unsubstituted with deuterium; a divalent dibenzofuran group; or a divalent dibenzothiophene group.

[0332] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

[0333] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic to tetracyclic aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic to tetracyclic heterocyclic group having 6 to 20 carbon atoms.

[0334] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently represent a phenyl group unsubstituted or substituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a biphenyl group unsubstituted or substituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthyl group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a thiophene group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a dibenzofuran group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthobenzofuran group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a dibenzothiophene group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or, it is a naphthobenzothiophene group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0335] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and are each independently a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a terphenyl group; a naphthyl group substituted or unsubstituted with deuterium; a thiophene group substituted or unsubstituted with a phenyl group; a phenanthrene group; a dibenzofuran group; a naphthobenzofuran group; a dibenzothiophene group; or a naphthobenzothiophene group.

[0336] In one embodiment of the present specification, Ar20 is a substituted or unsubstituted heterocyclic group, and Ar21 is a substituted or unsubstituted aryl group.

[0337] According to one embodiment of the present specification, R201 is hydrogen; or a phenyl group.

[0338] According to one embodiment of the present specification, the chemical formula H-1 is represented by the following compound.

[0339]

[0340] The above dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, the aromatic amine derivatives are condensed aromatic ring derivatives having a substituted or unsubstituted arylamine group, such as pyrene, anthracene, chrysene, and periflanthene having an arylamine group. In addition, the styrylamine compound is a compound in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and one or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group are substituted or unsubstituted. Specifically, the present invention includes, but is not limited to, styrylamine, styryldiamine, styryltriamine, and styryltetraamine. In addition, the metal complexes include, but are not limited to, iridium complexes, platinum complexes, and the like.

[0341] According to one embodiment of the present specification, the dopant includes, but is not limited to, a compound represented by the following chemical formula D-1.

[0342] [Chemical Formula D-1]

[0343]

[0344] In the above chemical formula D-1,

[0345] T1 to T6 are the same or different and are each independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkylsilyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

[0346] t5 and t6 are integers from 1 to 4, respectively.

[0347] If the above t5 is 2 or more, the two or more T5 are the same or different from each other,

[0348] When the above t6 is 2 or more, the two or more T6 are the same or different from each other.

[0349] According to one embodiment of the present specification, T1 to T6 are the same as or different from each other, and are each independently hydrogen; a substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted straight-chain or branched-chain alkylsilyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

[0350] According to one embodiment of the present specification, T1 to T6 are the same as or different from each other, and each independently represent hydrogen; a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; a straight-chain or branched-chain alkylsilyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium, a cyano group, or a straight-chain or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

[0351] According to one embodiment of the present specification, T1 to T6 are the same as or different from each other, and are each independently hydrogen; an isopropyl group; a trimethylsilyl group; a phenyl group substituted with deuterium; a phenyl group substituted with a cyano group; or a phenyl group substituted with a methyl group.

[0352] According to one embodiment of the present specification, the chemical formula D-1 is represented by the following compound.

[0353]

[0354] The above-mentioned hole injection layer is a layer that receives holes from the electrode. It is preferable that the hole injection material has the ability to transport holes, thereby having a hole receiving effect from the anode and an excellent hole injection effect into the light-emitting layer or light-emitting material. In addition, a material having an excellent ability to prevent the movement of excitons generated in the light-emitting layer to the electron injection layer or electron injection material is preferable. In addition, a material having an excellent thin film forming ability is preferable. In addition, it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, and arylamine series organic materials; hexanitrilehexaazatriphenylene series organic materials; quinacridone series organic materials; perylene series organic materials; There are conductive polymers of the polythiophene series, such as anthraquinone and polyaniline, but they are not limited thereto.

[0355] According to one embodiment of the present specification, the hole injection layer includes, but is not limited to, a compound represented by the following chemical formula HI-1.

[0356] [Chemical formula HI-1]

[0357]

[0358] In the above chemical formula HI-1,

[0359] R301 to R306 are the same or different and each independently represent hydrogen; deuterium; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

[0360] L301 and L302 are the same or different, and each independently represent a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group.

[0361] According to the temporary state of this specification, R301 and R302 are the same as or different from each other, and each independently represents a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms.

[0362] According to one embodiment of the present specification, R301 and R302 are methyl groups.

[0363] According to one embodiment of the present specification, L301 and L302 are direct bonds.

[0364] According to one embodiment of the present specification, R303 to R306 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

[0365] According to one embodiment of the present specification, R303 to R306 are the same as or different from each other, and each independently represents a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, which is unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0366] According to one embodiment of the present specification, R303 to R306 are the same as or different from each other, and each independently represents a phenyl group; or a carbazole group substituted or unsubstituted with a phenyl group.

[0367] According to one embodiment of the present specification, the chemical formula HI-1 is represented by the following compound.

[0368]

[0369] The above-mentioned hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light-emitting layer. The hole transport material is preferably a material with high hole mobility that can receive holes from the anode or the hole injection layer and transport them to the light-emitting layer. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated portions.

[0370] According to one embodiment of the present specification, the hole transport layer includes, but is not limited to, a compound represented by the following chemical formula HT-1.

[0371] [Chemical formula HT-1]

[0372]

[0373] In the above chemical formula HT-1,

[0374] At least one of X'1 to X'6 is N, and the rest are CH,

[0375] R309 to R314 are the same or different, and each independently represent hydrogen; deuterium; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or combine with adjacent groups to form a substituted or unsubstituted ring.

[0376] According to one embodiment of the present specification, X'1 to X'6 are N.

[0377] According to one embodiment of the present specification, R309 to R314 are cyano groups.

[0378] According to one embodiment of the present specification, the chemical formula HT-1 is represented by the following compound.

[0379]

[0380] According to one embodiment of the present specification, the hole transport layer includes, but is not limited to, a compound represented by the following chemical formula HT-2.

[0381] [Chemical formula HT-2]

[0382]

[0383] In the above chemical formula HT-2,

[0384] R315 to R317 are the same or different, and each independently represent one selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and combinations thereof, or combine with adjacent groups to form a substituted or unsubstituted ring,

[0385] r315 is an integer from 1 to 5, and when r315 is 2 or more, 2 or more R315 are the same as or different from each other,

[0386] r316 is an integer from 1 to 5, and when r316 is 2 or more, two or more R316 are the same as or different from each other.

[0387] According to one embodiment of the present specification, R317 is any one selected from the group consisting of a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and a combination thereof.

[0388] According to one embodiment of the present specification, R317 is any one selected from the group consisting of a carbazole group; a phenyl group; a biphenyl group; and combinations thereof.

[0389] According to one embodiment of the present specification, R315 and R316 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group, or are combined with an adjacent group to form an aromatic hydrocarbon ring substituted with an alkyl group.

[0390] According to one embodiment of the present specification, R315 and R316 are the same as or different from each other, and each independently represents a phenyl group, or are combined with an adjacent group to form an indene substituted with a methyl group.

[0391] According to one embodiment of the present specification, the chemical formula HT-2 is represented by the following compound.

[0392]

[0393] The electron transport layer is a layer that receives electrons from the electron injection layer and transports them to the light-emitting layer. When the organic light-emitting device according to one embodiment of the present specification includes an additional electron transport layer in addition to the electron transport layer comprising the chemical formula 1, 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 having high electron mobility is preferable. Specific examples include, but are not limited to, Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; and hydroxyflavone-metal complexes. The electron transport layer can be used with any desired cathode material, as used according to the prior art. In particular, suitable cathode materials are conventional materials having a low work function and followed by an aluminum layer or a silver layer. Specifically, there are cesium, barium, calcium, ytterbium, and samarium, and in each case followed by an aluminum layer or a silver layer.

[0394] The electron injection layer is a layer that receives electrons from the electrode. When the organic light-emitting device according to one embodiment of the present specification includes an additional electron injection layer other than the electron injection layer comprising the chemical formula 1, it is preferable that the electron injection material has an excellent ability to transport electrons, an electron receiving effect from the second electrode, and an excellent electron injection effect for the light-emitting layer or the light-emitting material. In addition, a material that prevents excitons generated in the light-emitting layer from moving to the hole injection layer and has an excellent thin film forming ability is preferable. Specifically, examples thereof include, but are not limited to, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone, and their derivatives, metal complex compounds, and nitrogen-containing 5-membered ring derivatives.

[0395] The above 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, Examples include, but are not limited to, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc.

[0396] According to one embodiment of the present specification, the electron injection and transport layer is a layer that transports electrons to the light-emitting layer. The electron injection and transport layer material may use a compound represented by the above chemical formula 1, and when an additional electron injection and transport layer is included in addition to the electron injection and electron transport layer including the above chemical formula 1, the materials exemplified in the electron transport layer and electron injection layer may be used, but are not limited thereto.

[0397] According to one embodiment of the present specification, the organic layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer includes the compound. The electron injection layer, the electron transport layer, or the electron injection and transport layer including the compound further includes a metal or a metal complex compound.

[0398] According to one embodiment of the present specification, the organic layer includes an electron injection and transport layer, and the electron injection and transport layer includes the compound. The electron injection and transport layer including the compound further includes a metal or a metal complex compound.

[0399] According to one embodiment of the present specification, the organic layer includes an electron injection and transport layer, and the electron injection and transport layer includes the compound. The electron injection and transport layer including the compound further includes a metal complex compound.

[0400] The above metal or metal complex compound may use the materials described above.

[0401] According to one embodiment of the present specification, the compound: metal, or metal complex is included in a weight ratio of 1:99 to 99:1, specifically in a weight ratio of 10:90 to 90 to 10, and even more specifically in a weight ratio of 50:50.

[0402] The electron blocking layer is a layer that can improve the lifespan and efficiency of a device by preventing electrons injected from the electron injection layer from passing through the light-emitting layer and entering the hole injection layer. Known materials can be used without limitation, and can be formed between the light-emitting layer and the hole injection layer, or between the light-emitting layer and a layer that simultaneously injects and transports holes.

[0403] The above hole blocking layer is a layer that blocks holes from reaching the cathode, and can generally be formed under the same conditions as the electron injection layer. When the organic light-emitting device according to one embodiment of the present specification includes an additional hole blocking layer other than the hole blocking layer including the chemical formula 1, specifically, the hole blocking layer includes, but is not limited to, an oxadiazole derivative, a triazole derivative, a phenanthroline derivative, an aluminum complex, etc.

[0404] The organic light-emitting device according to the present specification may be a front-emitting, back-emitting or double-sided emitting device depending on the material used.

[0405] The organic light-emitting device according to the present specification can be incorporated into and used in various electronic devices. For example, the electronic devices may be, but are not limited to, display panels, touch panels, solar modules, lighting devices, etc.

[0406] Hereinafter, the present specification will be described in detail with examples and comparative examples. However, the examples and comparative examples according to the present specification may be modified in various different forms, and the scope of the present specification is not construed as being limited to the examples and comparative examples described below. The examples and comparative examples of the present specification are provided to more fully explain the present specification to those with average knowledge in the art.

[0407] Manufacturing example 1.

[0408]

[0409] 2-Bromo-1-chloro-3-iodobenzene (9.52 g, 30 mmol) and the above compound isoquinolin-1-ylboronic acid (5.7 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K2CO3 (200 mL) and tetrakis(triphenylphosphine)palladium(0) (0.3 g) were added, and the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the mixture was filtered, and the resulting solid was recrystallized twice with toluene to prepare the above compound 1-1.

[0410] The above compounds 1-1 (9.6 g, 30 mmol) and 1-2 (11.66 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K2CO3 (200 mL), Palladium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with toluene to prepare the above compound 1-3.

[0411] The above compounds 1-3 (16.41 g, 30 mmol) and 1-4 (11.66 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K2CO3 (200 mL), Palladium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with toluene to prepare the above compound 1.

[0412] (19.68 g, yield 80%, MS:[M+H]+= 820).

[0413] Manufacturing example 2.

[0414]

[0415] Compound 2 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0416] MS: [M+H] + = 897

[0417] Manufacturing example 3.

[0418]

[0419] Compound 3 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0420] MS: [M+H] + = 897

[0421] Manufacturing example 4.

[0422]

[0423] Compound 4 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0424] MS: [M+H] + = 834

[0425] Manufacturing Example 5.

[0426]

[0427] Compound 5 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0428] MS: [M+H] + = 910

[0429] Manufacturing example 6.

[0430]

[0431] Compound 6 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0432] MS: [M+H] + = 810

[0433] Manufacturing example 7.

[0434]

[0435] Compound 7 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0436] MS: [M+H] + = 876

[0437] Manufacturing example 8.

[0438]

[0439] Compound 8 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0440] MS: [M+H] + = 868

[0441] Manufacturing example 9.

[0442]

[0443] Compound 9 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0444] MS: [M+H] + = 870

[0445] Manufacturing example 10.

[0446]

[0447] Compound 10 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0448] MS: [M+H] + = 870

[0449] Manufacturing example 11.

[0450]

[0451] Compound 11 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0452] MS: [M+H] + = 910

[0453] Manufacturing example 12.

[0454]

[0455] Compound 12 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0456] MS: [M+H] + = 895

[0457] Manufacturing example 13.

[0458]

[0459] Compound 13 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0460] MS: [M+H] + = 894

[0461] Manufacturing example 14.

[0462]

[0463] Compound 14 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0464] MS: [M+H] + = 819

[0465] Manufacturing example 15.

[0466]

[0467] Compound 15 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0468] MS: [M+H] + = 834

[0469] Manufacturing example 16.

[0470]

[0471] Compound 16 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0472] MS: [M+H] + = 793

[0473] Manufacturing example 17.

[0474]

[0475] Compound 17 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0476] MS: [M+H] + = 821

[0477] Manufacturing example 18.

[0478]

[0479] Compound 18 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0480] MS: [M+H] + = 910

[0481] Manufacturing example 19.

[0482]

[0483] Compound 19 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0484] MS: [M+H] + = 819

[0485]

[0486] Example 1-1

[0487] A glass substrate coated with a 1000 Å thick ITO (indium tin oxide) film was placed in distilled water containing detergent and ultrasonically cleaned. The detergent was a Fischer Co. product, and the distilled water was filtered twice using a Millipore Co. filter. After washing the ITO for 30 minutes, ultrasonically cleaned twice with distilled water for 10 minutes each. After washing with distilled water, ultrasonically cleaned with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transferred to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using oxygen plasma and then transferred to a vacuum deposition machine.

[0488] On the ITO transparent electrode thus prepared, the following compound HI-A was thermally vacuum deposited to a thickness of 600 Å to form a hole injection layer. On the hole injection layer, the following compound HAT at 50 Å and the following compound HT-A at 60 Å were sequentially vacuum deposited to form a first hole transport layer and a second hole transport layer.

[0489] Next, a light-emitting layer was formed by vacuum-depositing the following compounds BH and BD at a weight ratio of 25:1 to a film thickness of 200 Å on the second hole transport layer.

[0490] On the above-mentioned light-emitting layer, the previously prepared compound 1 and the following compound LiQ were vacuum-deposited at a weight ratio of 1:1 to form an electron injection and transport layer with a thickness of 350 Å. On the above-mentioned electron injection and transport layer, lithium fluoride (LiF) was sequentially deposited with a thickness of 10 Å and aluminum was sequentially deposited with a thickness of 1000 Å to form a cathode.

[0491]

[0492] In the above process, the deposition rate of organic materials was maintained at 0.4 Å / sec to 0.9 Å / sec, the lithium fluoride of the cathode was maintained at 0.3 Å / sec, and the aluminum was maintained at 2 Å / sec, and the vacuum during deposition was 1 × 10 -7 torr to 5 × 10 -5 torr, and an organic light-emitting device was manufactured.

[0493] Examples 1-2 to 1-19

[0494] An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that compounds 2 to 19 described in Table 1 below were used instead of compound 1 of Example 1-1.

[0495]

[0496] Comparative Examples 1-1 to 1-4

[0497] An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that compounds ET-1 to ET-4 in Table 1 below were used instead of compound 1 in Example 1-1. The structures of compounds ET-1 to ET-4 in Table 1 below are as follows.

[0498]

[0499] Component evaluation

[0500] 10 mA / cm for the organic light-emitting devices manufactured in Examples 1-1 to 1-19 and Comparative Examples 1-1 to 1-4 2 The driving voltage and luminous efficiency were measured at a current density of 20 mA / cm 2 The time (T90) at which the initial luminance reaches 90% of the current density was measured. The results are shown in Table 1 below.

[0501] Distinctive compound voltage (V) (@10 mA / cm) 2 )Efficiency (cd / A) (@10 mA / cm 2 )Color coordinates (x, y)Lifespan (hr) (T90 at 20 mA / cm 2) Example 1-114.334.94(0.140, 0.091)180 Example 1-224.295.00(0.140, 0.092)190 Example 1-334.374.84(0.140, 0.092)200 Example 1-444.334.88(0.141, 0.092)205 Example 1-554.364.75(0.140, 0.093)215 Example 1-664.304.81(0.140, 0.092)205 Example 1-774.204.99(0.140, 0.093)200 Example 1-884.264.89(0.140, 0.091)210 Example 1-994.374.73(0.140, 0.092)205 Example 1-10104.404.77(0.140, 0.092)185 Example 1-11114.364.74(0.141, 0.092)205 Example 1-12124.404.63(0.141, 0.091)185 Example 1-13134.414.63(0.140, 0.094)190 Example 1-14144.444.52(0.140, 0.093)190 Example 1-15 154.38 4.71 (0.140, 0.092) 180 Example 1-16 164.4 14.50 (0.141, 0.091) 160 Example 1-17 174.30 4.21 (0.140, 0.094) 175 Example 1-18 184.44 4.05 (0.140, 0.093) 180 Example 1-19 194.4 14.40 (0.140, 0.092) 175 Comparative Example 1-1ET-14.5 0 2.69 (0.140, 0.092) 100 Comparative Example 1-2ET-24.5 14.17 (0.140, 0.092) 35 Comparative Example 1-3ET-34.534.01(0.140, 0.092)36Comparative example 1-4ET-44.354.00(0.141, 0.093)30

[0502] As described in Table 1 above, the compound represented by Chemical Formula 1 according to the present specification can be used in the electron injection and transport layer of an organic light-emitting device. Chemical Formula 1 according to an exemplary embodiment of the present specification is a compound having a benzene core to which a bicyclic heterocycle containing 1 or 2 Ns is bonded, and which necessarily includes an arylene group as a linking group on both sides of the benzene, and which includes a monocyclic or bicyclic heteroaryl group containing 2 or 3 Ns as a substituent, and which has an electron depletion structure, so that the polarity (dipole moment) of the molecule can be increased, and thus, when manufacturing an organic light-emitting device including the compound represented by Chemical Formula 1, electron mobility is smoothly controlled, and the organic light-emitting devices including the same, Examples 1-1 to 1-19, have the effects of low voltage, high efficiency, and long life.

[0503] Specifically, it can be seen that the above Examples 1-1 to 1-19 are superior to Comparative Examples 1-1 and 1-2 in terms of driving voltage, efficiency, and lifespan, including a compound in which at least one of L1 and L2, which are connecting groups on both sides of benzene of Chemical Formula 1 of the present specification, is a direct bond.

[0504] It can be seen that the above Examples 1-1 to 1-19 are superior in terms of operating voltage, efficiency and lifespan to Comparative Example 1-3, which includes a compound containing a monocyclic N-containing heterocyclic group instead of the dicyclic N-containing heterocyclic group of the present specification.

[0505] In addition, it can be seen that the above Examples 1-1 to 1-19 are superior in efficiency and lifespan to Comparative Example 1-4, which includes a compound containing a naphthyl group instead of the N-containing heterocyclic group of the present specification.

Claims

1. A compound of the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, One or two of Y1 to Y8 are N, one of the others is C bonded to chemical formula 1, and the others are each independently CR3, X1 is N or CR'1, X2 is N or CR'2, R'1 is hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; or a moiety bonded to L1, or bonded to R1 to form a substituted or unsubstituted aromatic hydrocarbon ring, R'2 is hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; or a moiety bonded to L2, or bonded to R2 to form a substituted or unsubstituted aromatic hydrocarbon ring, R1 and R2 are the same or different from each other, and each independently represents a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or are combined with an adjacent group to form a substituted or unsubstituted aromatic hydrocarbon ring, R3 is hydrogen; deuterium; or a substituted or unsubstituted alkyl group, L1 and L2 are the same or different and are each independently a substituted or unsubstituted arylene group, n1 and n2 are integers from 1 to 5, respectively, r1 and r2 are integers from 1 to 3, respectively, If the above n1 is 2 or more, the above 2 or more L1s are equal to or different from each other, If the above n2 is 2 or more, the above 2 or more L2s are equal to or different from each other, When the above r1 is 2 or more, the two or more R1 are the same or different from each other, When the above r2 is 2 or more, the two or more R2 are equal to or different from each other.

2. In claim 1, the chemical formula 1 is a compound which is any one of the following chemical formulas 1-1 to 1-6: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] [Chemical Formula 1-5] [Chemical Formula 1-6] In the above chemical formulas 1-1 to 1-6, The definitions of Y1 to Y8, X1, X2, R1, R2, r1, r2, L1, L2, n1 and n2 are the same as defined in the chemical formula 1 above.

3. In claim 1, the chemical formula 1 is a compound having the following chemical formula 2: [Chemical formula 2] In the above chemical formula 2, The definitions of Y1 to Y8, X1, X2, R1, R2, r1 and r2 are the same as defined in the chemical formula 1 above.

4. In claim 1, the chemical formula 1 A compound having one of the following structures: In the above structure, * is a part that is bonded to the chemical formula 1 above, R31 to R38 are the same or different, and each independently represent hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

5. In claim 1, the chemical formula 1 A compound having one of the following structures: In the above structure, * is the part that is bonded to chemical formula 1, The definitions of L1, n1, R1, r1 and R'1 are the same as those defined in the chemical formula 1 above, R101 is hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, r101 is an integer from 1 to 4, When the above r101 is 2 or more, the two or more R101 are equal to or different from each other.

6. In claim 1, the chemical formula 1 A compound having one of the following structures: In the above structure, * is the part that is bonded to chemical formula 1, The definitions of L2, n2, R2, r2 and R'2 are the same as those defined in the chemical formula 1 above, R201 is hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, R201 is an integer from 1 to 4, When the above r201 is 2 or more, the two or more R201 are equal to or different from each other.

7. In claim 1, the chemical formula 1 and are compounds which are identical to each other: * is the part that is bonded to chemical formula 1, The definitions of L2, n2, R2, r2 and R'2 are the same as those defined in the chemical formula 1 above.

8. In claim 1, R1 and R2 are the same as or different from each other, and each independently represents a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, substituted or unsubstituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, substituted or unsubstituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, substituted or unsubstituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic heteroaryl group having 6 to 30 carbon atoms, The above R'1 is hydrogen; deuterium; a straight or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a moiety bonded to L1, The above R'2 is hydrogen; deuterium; a straight or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a moiety bonded to L2, The above L1 and L2 are the same or different from each other, and each independently represents a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms, A compound wherein the above R3 is hydrogen; deuterium; or a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms.

9. In claim 1, the compound having chemical formula 1 is any one of the following compounds: .

10. An organic light-emitting device comprising a first electrode; a second electrode; and at least one organic layer provided between the first electrode and the second electrode, wherein at least one of the organic layers comprises a compound according to any one of claims 1 to 9.

11. An organic light-emitting device according to claim 10, wherein the organic layer comprises an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer comprises the compound.

12. An organic light-emitting device according to claim 10, wherein the organic layer includes a hole blocking layer, and the hole blocking layer includes the compound.

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