Compound and organic light-emitting device comprising same

Abstract

The present specification relates to a compound of chemical formula 1 and an organic light-emitting device comprising same. Through the balance of holes and electrons of the organic light-emitting device according to the chemical structure of chemical formula 1, efficiency can be improved, and low driving voltage and / or lifespan characteristics can be improved.

Description

Compound and organic light-emitting device containing the same

[0001] This application claims the benefit of Korean Patent Application No. 10-2024-0027048, filed with the Korean Intellectual Property Office on February 26, 2024, the entire contents of which are incorporated herein by reference.

[0002] The present specification relates to a compound and an organic light-emitting device comprising the same.

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

[0006] One embodiment of the present disclosure provides a compound of the following chemical formula 1.

[0007] [Chemical Formula 1]

[0008]

[0009] In the above chemical formula 1,

[0010] At least two of X1 to X3 are N, and the rest are CH,

[0011] At least two of X4 to X6 are N, and the rest are CH,

[0012] R1 to R11 are the same or different and are each independently hydrogen; deuterium; or cyano group,

[0013] r10 is 1 or 2, and when said r10 is 2, said two R10s are equal to or different from each other,

[0014] r11 is an integer from 1 to 4, and when r11 is 2 or more, 2 or more R11 are the same or different,

[0015] Ar1 to Ar4 are the same or different from each other, and are each independently hydrogen; deuterium; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

[0016] ar1 is an integer from 1 to 5, and when ar1 is 2 or more, 2 or more Ar1 are equal to or different from each other,

[0017] ar2 is an integer from 1 to 5, and when ar2 is 2 or more, 2 or more Ar2 are the same or different from each other,

[0018] ar3 is an integer from 1 to 5, and when ar3 is 2 or more, 2 or more Ar3 are the same or different from each other,

[0019] ar4 is an integer from 1 to 5, and when ar4 is 2 or more, 2 or more Ar4 are the same as or different from each other,

[0020] One or two of Y1 to Y5 are N, and the others are each independently CR'1,

[0021] R'1 is hydrogen; deuterium; a cyano group; or a substituted or unsubstituted alkyl group, or is bonded to an adjacent group to form a substituted or unsubstituted aromatic hydrocarbon ring.

[0022] 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.

[0023] 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 preferably can be used in an electron injection layer, an electron transport layer, or an electron injection and transport layer.

[0024] By using this, it is possible to improve efficiency, lower driving voltage and / or improve life characteristics in organic light-emitting devices.

[0025] Figures 1 and 2 illustrate examples of organic light-emitting devices according to one embodiment of the present specification.

[0026] [Explanation of symbols]

[0027] 1: Substrate

[0028] 2: First electrode

[0029] 3: Organic layer

[0030] 4: Second electrode

[0031] 5: Hole injection layer

[0032] 6: Hole transport layer

[0033] 7: Electron suppression layer

[0034] 8: Emissive layer

[0035] 9: The hole-blocking layer

[0036] 10: Electron injection and transport layer

[0037] Hereinafter, the present specification will be described in more detail.

[0038] One embodiment of the present specification provides a compound of the above chemical formula 1.

[0039] According to one embodiment of the present disclosure, the chemical formula 1 substitutes an N-containing heterocycle between diphenyltriazine or diphenylpyrimidine, which serve as electron donors and acceptors, so that an organic light-emitting device including the same has low-voltage and high-efficiency characteristics by controlling electron mobility. In addition, the N-containing monocyclic heterocycle of the chemical formula 1 of the present disclosure is a heterocycle that serves as an electron withdrawer, thereby lowering the LUMO value, so that an organic light-emitting device including the same has effective long-life characteristics.

[0040] 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.

[0041] Examples of substituents in this specification are described below, but are not limited thereto.

[0042] In this specification, means the connecting part.

[0043] 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.

[0044] 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.

[0045] 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.

[0046] In this specification, examples of halogen groups include a fluoro group, a chloro group, a bromo group, or an iodo group.

[0047] 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.

[0048] 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.

[0049] 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.

[0050] 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.

[0051] 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.

[0052] 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.

[0053] 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.

[0054] 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.

[0055] In the present specification, the fluorene group may be substituted, and adjacent groups may be combined with each other to form a ring.

[0056] When the above fluorene group is substituted, There are, but are not limited to, the following.

[0057] 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.

[0058] 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.

[0059] 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.

[0060] 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.

[0061] 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.

[0062] 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.

[0063] 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.

[0064] 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.

[0065] 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.

[0066] 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.

[0067] 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.

[0068] 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.

[0069] 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.

[0070] 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.

[0071] 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.

[0072] 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.

[0073] 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.

[0074] 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.

[0075] 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.

[0076] 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.

[0077] Hereinafter, the compound represented by the chemical formula 1 will be described in detail.

[0078] According to one embodiment of the present specification, the chemical formula 1 is any one of the following chemical formulas 1-1 to 1-5.

[0079] [Chemical Formula 1-1]

[0080]

[0081] [Chemical Formula 1-2]

[0082]

[0083] [Chemical Formula 1-3]

[0084]

[0085] [Chemical Formula 1-4]

[0086]

[0087] [Chemical Formula 1-5]

[0088]

[0089] In the above chemical formulas 1-1 to 1-5,

[0090] The definitions of X1 to X6, Y1 to Y5, R1 to R9, R11, r11, Ar1 to Ar4 and ar1 to ar4 are the same as those defined in the above chemical formula 1,

[0091] R101 to R104 are the same or different, and each independently represent hydrogen; deuterium; or cyano group.

[0092] According to one embodiment of the present specification, the chemical formula 1 is any one of the following chemical formulas 1-6 to 1-9.

[0093] [Chemical Formula 1-6]

[0094]

[0095] [Chemical Formula 1-7]

[0096]

[0097] [Chemical Formula 1-8]

[0098]

[0099] [Chemical Formula 1-9]

[0100]

[0101] In the above chemical formulas 1-6 to 1-9,

[0102] The definitions of X1 to X6, Y1 to Y5, R1 to R11, r10, r11, Ar1 to Ar4 and ar1 to ar4 are the same as those defined in the above chemical formula 1.

[0103] According to one embodiment of the present specification, Y1 is N, and Y2 to Y5 are each independently CR'1.

[0104] According to one embodiment of the present specification, Y2 is N, and Y1 and Y3 to Y5 are each independently CR'1.

[0105] According to one embodiment of the present specification, Y3 is N, and Y1, Y2, Y4 and Y5 are each independently CR'1.

[0106] According to one embodiment of the present specification, Y1 and Y2 are N, and Y3 to Y5 are each independently CR'1.

[0107] According to one embodiment of the present specification, Y1 and Y3 are N, and Y2, Y4 and Y5 are each independently CR'1.

[0108] According to one embodiment of the present specification, Y1 and Y4 are N, and Y2, Y3 and Y5 are each independently CR'1.

[0109] According to one embodiment of the present specification, Y1 and Y5 are N, and Y2 to Y4 are each independently CR'1.

[0110] According to one embodiment of the present specification, Y2 and Y3 are N, and Y1, Y4 and Y5 are each independently CR'1.

[0111] According to one embodiment of the present specification, Y2 and Y4 are N, and Y1, Y3 and Y5 are each independently CR'1.

[0112] According to one embodiment of the present specification, Y2 and Y5 are N, and Y1, Y3 and Y4 are each independently CR'1.

[0113] According to one embodiment of the present specification, Y3 and Y4 are N, and Y1, Y2 and Y5 are each independently CR'1.

[0114] According to one embodiment of the present specification, Y3 and Y5 are N, and Y1, Y2 and Y4 are each independently CR'1.

[0115] According to one embodiment of the present specification, the chemical formula 1 is one of the following structural formulas.

[0116]

[0117] In the above structural formula,

[0118] * is a site that is bonded to the above chemical formula 1,

[0119] R'11 to R'15 are the same or different, and each independently represents hydrogen; deuterium; a cyano group; or a substituted or unsubstituted alkyl group, or combine with an adjacent group to form a substituted or unsubstituted aromatic hydrocarbon ring.

[0120] According to one embodiment of the present specification, X1 to X3 are N.

[0121] According to one embodiment of the present specification, X1 and X2 are N, and X3 is CH.

[0122] According to one embodiment of the present specification, X1 and X3 are N, and X2 is CH.

[0123] According to one embodiment of the present specification, X2 and X3 are N, and X1 is CH.

[0124] According to one embodiment of the present specification, X4 to X6 are N.

[0125] According to one embodiment of the present specification, X4 and X5 are N, and X6 is CH.

[0126] According to one embodiment of the present specification, X4 and X6 are N, and X5 is CH.

[0127] According to one embodiment of the present specification, X5 and X6 are N, and X4 is CH.

[0128] According to one embodiment of the present specification, the chemical formula 1 is one of the following structures.

[0129]

[0130] In the above structural formula,

[0131] * is the site that binds to chemical formula 1,

[0132] The definitions of Ar1, Ar2, ar1 and ar2 are the same as those defined in the chemical formula 1 above.

[0133] According to one embodiment of the present specification, the chemical formula 1 is one of the following structures.

[0134]

[0135] In the above structural formula,

[0136] * is the site that binds to chemical formula 1,

[0137] The definitions of Ar3, Ar4, ar3 and ar4 are the same as those defined in the above chemical formula 1.

[0138] According to one embodiment of the present specification, the chemical formula 1 and are different from each other.

[0139] According to one embodiment of the present specification, the chemical formula 1 and are identical to each other.

[0140] According to one embodiment of the present specification, R1 to R11 are the same as or different from each other, and are each independently hydrogen; deuterium; or cyano group.

[0141] According to one embodiment of the present specification, R1 to R11 are hydrogen.

[0142] According to one embodiment of the present specification, R1 to R11 are deuterium.

[0143] According to one embodiment of the present specification, at least one of R1 to R11 is deuterium.

[0144] According to one embodiment of the present specification, R1 to R11 are cyano groups.

[0145] According to one embodiment of the present specification, at least one of R1 to R11 is a cyano group.

[0146] According to one embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and are each independently hydrogen; deuterium; a cyano group; 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 monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

[0147] The above R'1 is hydrogen; deuterium; a cyano group; or a straight or branched alkyl group having 1 to 30 carbon atoms, or is bonded to an adjacent group to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms.

[0148] According to one embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and are each independently hydrogen; deuterium; cyano group; methyl group; or pyridine group.

[0149] According to one embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted cyano group; a substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; a 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.

[0150] According to one embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted cyano group; a substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to 20 carbon atoms; a 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.

[0151] According to one embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and are each independently hydrogen; deuterium; cyano group; alkyl group; aryl group; or heteroaryl group.

[0152] According to one embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and are each independently hydrogen; deuterium; a cyano group; 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 monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

[0153] According to one embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and are each independently hydrogen; deuterium; a cyano group; a straight or branched alkyl group having 1 to 20 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms.

[0154] According to one embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and are each independently hydrogen; deuterium; or cyano group.

[0155] According to one embodiment of the present specification, Ar1 to Ar4 are hydrogen.

[0156] According to one embodiment of the present specification, Ar1 to Ar4 are deuterium.

[0157] According to one embodiment of the present specification, Ar1 to Ar4 are cyano groups.

[0158] According to one embodiment of the present specification, at least one of Ar1 to Ar4 is deuterium.

[0159] According to one embodiment of the present specification, one of Ar1 to Ar4 is deuterium.

[0160] According to one embodiment of the present specification, two of Ar1 to Ar4 are deuterium.

[0161] According to one embodiment of the present specification, three of Ar1 to Ar4 are deuterium.

[0162] According to one embodiment of the present specification, at least one of Ar1 to Ar4 is a cyano group.

[0163] According to one embodiment of the present specification, two of Ar1 to Ar4 are cyano groups.

[0164] According to one embodiment of the present specification, three of Ar1 to Ar4 are cyano groups.

[0165] According to one embodiment of the present specification, R'1 is hydrogen; deuterium; a cyano group; or a substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms, or is bonded to an adjacent group to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms.

[0166] According to one embodiment of the present specification, R'1 is hydrogen; deuterium; a cyano group; or a substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to 20 carbon atoms, or is bonded to an adjacent group to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms.

[0167] According to one embodiment of the present specification, R'1 is hydrogen; deuterium; a cyano group; or an alkyl group, or is bonded to an adjacent group to form an aromatic hydrocarbon ring.

[0168] According to one embodiment of the present specification, R'1 is hydrogen; deuterium; a cyano group; or a straight or branched alkyl group having 1 to 30 carbon atoms, or is bonded to an adjacent group to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms.

[0169] According to one embodiment of the present specification, R'1 is hydrogen; deuterium; a cyano group; or a straight or branched alkyl group having 1 to 20 carbon atoms, or is bonded to an adjacent group to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms.

[0170] According to one embodiment of the present specification, R'1 is hydrogen; deuterium; a cyano group; or a methyl group, or is bonded to an adjacent group to form a benzene ring.

[0171] According to one embodiment of the present specification, R'1 is hydrogen; deuterium; a cyano group; or a substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms.

[0172] According to one embodiment of the present specification, R'1 is hydrogen; deuterium; a cyano group; or a substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to 20 carbon atoms.

[0173] According to one embodiment of the present specification, R'1 is hydrogen; deuterium; a cyano group; or an alkyl group.

[0174] According to one embodiment of the present specification, R'1 is hydrogen; deuterium; a cyano group; or a straight or branched alkyl group having 1 to 30 carbon atoms.

[0175] According to one embodiment of the present specification, R'1 is hydrogen; deuterium; a cyano group; or a straight or branched chain alkyl group having 1 to 20 carbon atoms.

[0176] According to one embodiment of the present specification, R'1 is hydrogen; deuterium; cyano group; or methyl group.

[0177] According to one embodiment of the present specification, R'1 is bonded to an adjacent group to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms.

[0178] According to one embodiment of the present specification, R'1 is bonded to an adjacent group to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms.

[0179] According to one embodiment of the present specification, R'1 is bonded to an adjacent group to form an aromatic hydrocarbon ring.

[0180] According to one embodiment of the present specification, R'1 is bonded to an adjacent group to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms.

[0181] According to one embodiment of the present specification, R'1 is bonded to an adjacent group to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms.

[0182] According to one embodiment of the present specification, R'1 is bonded to an adjacent group to form a benzene ring.

[0183] According to one embodiment of the present specification, the chemical formula 1 is any one of the following compounds.

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211] One embodiment of the present specification provides an organic light-emitting device comprising a compound represented by the chemical formula 1.

[0212] 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.

[0213] 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.

[0214] 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.

[0215] 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.

[0216] 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.

[0217] 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.

[0218] 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 suppression 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.

[0219] 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.

[0220] According to one embodiment of the present specification, the organic layer includes a hole blocking layer, and the hole blocking layer includes the compound.

[0221] According to one embodiment of the present specification, the organic layer includes a light-emitting layer.

[0222] 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.

[0223] According to one embodiment of the present specification, the organic layer includes an electron blocking layer.

[0224] According to one embodiment of the present specification, the organic layer includes a hole blocking layer.

[0225] 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 suppression layer.

[0226] 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.

[0227] 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 suppression layer.

[0228] 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.

[0229] According to one embodiment of the present specification, the first electrode is an anode or a cathode.

[0230] According to one embodiment of the present specification, the second electrode is a cathode or an anode.

[0231] 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.

[0232] 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.

[0233] 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.

[0234] Figure 1 illustrates the structure of an organic light-emitting device in which a first electrode (2), an organic layer (3), and a second electrode (4) are sequentially laminated on a substrate (1). The compound represented by the chemical formula 1 is included in the organic layer.

[0235] FIG. 2 illustrates the structure of an organic light-emitting device in which a first electrode (2), a hole injection layer (5), a hole transport layer (6), an electron suppression layer (7), a light-emitting layer (8), a hole blocking layer (9), an electron injection and transport layer (10), and a second electrode (4) are sequentially laminated on a substrate (1). The compound represented by the chemical formula 1 is included in the electron injection and transport layer (10).

[0236] 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.

[0237] 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.

[0238] 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.

[0239] 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.

[0240] 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.

[0241] 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.

[0242] 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.

[0243] 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.

[0244] 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.

[0245] [Chemical formula HI-1]

[0246]

[0247] In the above chemical formula HI-1,

[0248] R400 to R402 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 amine group; a substituted or unsubstituted heteroaryl group; and combinations thereof, or combine with adjacent groups to form a substituted or unsubstituted ring,

[0249] L402 is a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.

[0250] According to one embodiment of the present specification, R400 to R402 are the same as or different from each other, and each independently is any one selected from the group consisting of a substituted or unsubstituted aryl group; a substituted or unsubstituted amine group; a substituted or unsubstituted heteroaryl group; and combinations thereof.

[0251] According to one embodiment of the present specification, R402 is any one selected from the group consisting of a phenyl group substituted with a carbazole group or an arylamine group; a biphenyl group substituted with a carbazole group or an arylamine group; and combinations thereof.

[0252] According to one embodiment of the present specification, R400 and R401 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group, or are bonded to an adjacent group to form an aromatic hydrocarbon ring substituted with an alkyl group.

[0253] According to one embodiment of the present specification, R400 and R401 are the same as or different from each other, and each independently represents an aryl group substituted or unsubstituted with an alkyl group.

[0254] According to one embodiment of the present specification, R400 and R401 are the same as or different from each other, and are each independently a phenyl group, a biphenyl group, or a dimethylfluorene group.

[0255] According to one embodiment of the present specification, the chemical formula HI-1 is selected from the following compounds.

[0256]

[0257] 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-2.

[0258] [Chemical formula HI-2]

[0259]

[0260] In the above chemical formula HI-2,

[0261] X'1 to X'3 are the same or different, and are each independently hydrogen, deuterium, or halogen group,

[0262] R309 to R314 are the same or different and are each independently hydrogen; deuterium; a nitrile 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,

[0263] x1' to x3' are each an integer from 1 to 4, and when they are 2 or more, the substituents in the parentheses are the same or different.

[0264] According to one embodiment of the present specification, X'1 to X'3 are halogen groups.

[0265] According to one embodiment of the present specification, X'1 to X'3 are F or Cl.

[0266] According to one embodiment of the present specification, X'1 to X'3 are F.

[0267] According to one embodiment of the present specification, R309 to R314 are the same as or different from each other, and are each independently hydrogen; deuterium; a nitrile group; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted amine group.

[0268] According to one embodiment of the present specification, R309 to R314 are the same as or different from each other, and are each independently hydrogen; deuterium; or nitrile.

[0269] According to one embodiment of the present specification, R309 to R314 are nitrile groups.

[0270] According to one embodiment of the present specification, the chemical formula HI-2 is represented by the following compound.

[0271]

[0272] 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.

[0273] 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.

[0274] [Chemical formula HT-2]

[0275]

[0276] In the above chemical formula HT-2,

[0277] R403 to R406 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 amine group; a substituted or unsubstituted heteroaryl group; and combinations thereof, or combine with adjacent groups to form a substituted or unsubstituted ring,

[0278] L403 is a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0279] l403 is an integer from 1 to 3, and if l403 is 2 or greater, L403 are equal to or different from each other.

[0280] According to one embodiment of the present specification, R403 to R406 are the same as or different from each other, and each independently is any one selected from the group consisting of a substituted or unsubstituted aryl group; a substituted or unsubstituted amine group; a substituted or unsubstituted heteroaryl group; and combinations thereof.

[0281] According to one embodiment of the present specification, R403 to R406 are the same as or different from each other, and each independently represents an aryl group having 6 to 30 carbon atoms.

[0282] According to one embodiment of the present specification, R403 to R406 are the same as or different from each other, and are each independently a phenyl group, a biphenyl group, or a naphthyl group.

[0283] According to one embodiment of the present specification, R403 to R406 are the same as or different from each other, and each independently is a phenyl group.

[0284] According to one embodiment of the present specification, the L403 is an arylene group having 6 to 30 carbon atoms, or a heteroarylene group having 3 to 30 carbon atoms substituted with an arylene group.

[0285] According to one embodiment of the present specification, the L403 is a divalent carbazole group substituted or unsubstituted with a phenylene group, a divalent biphenyl group, or an aryl group.

[0286] According to one embodiment of the present specification, the L403 is a divalent carbazole group substituted with a naphthyl group.

[0287] According to one embodiment of the present specification, the chemical formula HT-2 is selected from the following compounds.

[0288]

[0289] The electron suppression 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.

[0290] According to one embodiment of the present specification, the electron suppression layer includes, but is not limited to, a compound represented by the following chemical formula EB-1.

[0291] [Chemical formula EB-1]

[0292]

[0293] In the above chemical formula EB-1,

[0294] R318 to R320 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,

[0295] r318 is an integer from 1 to 5, and when r318 is 2 or more, 2 or more R318 are the same as or different from each other,

[0296] r319 is an integer from 1 to 5, and when r319 is 2 or more, two or more R319 are the same as or different from each other.

[0297] According to one embodiment of the present specification, R320 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.

[0298] According to one embodiment of the present specification, R320 is any one selected from the group consisting of a phenyl group, a biphenyl group, a carbazole group, and a combination thereof.

[0299] According to one embodiment of the present specification, R318 and R319 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.

[0300] According to one embodiment of the present specification, R318 and R319 are the same as or different from each other, and are each independently a phenyl group, a biphenyl group, or a phenanthrene group.

[0301] According to one embodiment of the present specification, the chemical formula EB-1 is represented by the following compound.

[0302]

[0303] 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.

[0304] 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.

[0305] [Chemical Formula H-1]

[0306]

[0307] In the above chemical formula H-1,

[0308] 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,

[0309] 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,

[0310] 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,

[0311] 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.

[0312] 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.

[0313] 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.

[0314] 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.

[0315] 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.

[0316] 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.

[0317] 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.

[0318] 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 aryl group.

[0319] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and are each independently a 1-naphthyl group or a 2-naphthyl group.

[0320] According to one embodiment of the present specification, R201 is hydrogen; or a phenyl group.

[0321] According to one embodiment of the present specification, the chemical formula H-1 is represented by the following compound.

[0322]

[0323] 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.

[0324] 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-2.

[0325] According to one embodiment of the present specification, the dopant is represented by a compound represented by the following chemical formula D-2.

[0326] [Chemical Formula D-2]

[0327]

[0328] In the above chemical formula D-2,

[0329] T1 to T5 are the same or different and are each independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amine group; or a substituted or unsubstituted aryl group,

[0330] t3 and t4 are integers from 1 to 4, respectively.

[0331] t5 is an integer from 1 to 3,

[0332] If the above t3 is 2 or more, the above 2 or more T3 are the same or different from each other,

[0333] If the above t4 is 2 or more, the two or more T4 are the same or different from each other,

[0334] When the above t5 is 2 or more, the two or more T5 are the same or different from each other.

[0335] According to one embodiment of the present specification, T1 to T5 are the same as or different from each other, and each independently represents hydrogen; a substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic arylamine group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0336] According to one embodiment of the present specification, T1 to T5 are the same as or different from each other, and each independently represents hydrogen; a straight or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic arylamine group having 6 to 30 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms which is unsubstituted or substituted with a straight or branched alkyl group having 1 to 30 carbon atoms.

[0337] According to one embodiment of the present specification, T1 to T5 are the same as or different from each other, and each independently represent hydrogen; a methyl group; an isopropyl group; a tert-butyl group; a diphenylamine group; or a phenyl group substituted or unsubstituted with a methyl group or a tert-butyl group.

[0338] According to one embodiment of the present specification, the chemical formula D-2 is represented by the compound below.

[0339]

[0340] 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.

[0341] 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.

[0342] 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.

[0343] 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.

[0344] 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.

[0345] 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.

[0346] 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. The metal or metal complex compound may use a material as described above.

[0347] 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.

[0348] 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.

[0349] According to one embodiment of the present specification, the hole-blocking layer includes a compound of the following chemical formula HB-1.

[0350] [Chemical formula HB-1]

[0351]

[0352] In the above chemical formula HB-1,

[0353] At least one of Z1 to Z3 is N, and the rest are CH,

[0354] L601 and L602 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 heteroarylene group,

[0355] Ar601 to Ar603 are the same or different, and each independently represents a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0356] According to one embodiment of the present specification, the L601 is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0357] According to one embodiment of the present specification, L601 and L602 are the same as or different from each other, and are each independently a phenylene group; a biphenylylene group; or a naphthylene group.

[0358] According to one embodiment of the present specification, Ar601 to Ar603 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms.

[0359] According to one embodiment of the present specification, Ar601 to Ar603 are a phenyl group or a spiro[cyclohexene-1,9'-fluorene group].

[0360] According to one embodiment of the present specification, the chemical formula HB-1 is represented by the following compound.

[0361]

[0362] 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.

[0363] 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.

[0364] The organic light-emitting device of the present invention can be manufactured using a conventional method and material for manufacturing an organic light-emitting device, except that one or more organic layers are formed using the above-described compound.

[0365] The method for preparing the compound of the above chemical formula 1 and the preparation of an organic light-emitting device using the compound are specifically described in the following examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited by them.

[0366] In the following reaction scheme, the type and number of substituents can be appropriately selected by those skilled in the art from known starting materials, enabling the synthesis of various types of intermediates. The reaction types and reaction conditions known in the art can be utilized.

[0367] Manufacturing Example 1. Synthesis of Chemical Formula E1

[0368] [Chemical Formula E1]

[0369]

[0370] The above compounds 6,6'-(5'-chloro-[1,1':3',1''-terphenyl]-2,2''-diyl)bis(2,4-diphenyl-1,3,5-triazine) (10.0 g, 13.8 mmol) and (3-(pyridin-3-yl)phenyl)boronic acid (2.74 g, 13.8 mmol) were completely dissolved in tetrahydrofuran (100 ml), then potassium carbonate (5.70, 41.3 mmol) dissolved in 17 ml of water was added, and tetrakistriphenylphosphinepalladium (477 mg, 0.4 mmol) dissolved in tetrahydrofuran was slowly added. After lowering the temperature to room temperature and terminating the reaction, the potassium carbonate solution was removed and the above white solid was filtered. The filtered white solid was washed twice with water and ethyl acetate, respectively, to prepare the compound of the above chemical formula E1 (9.9 g, yield 85%).

[0371] MS[M+H] + = 847

[0372] Manufacturing Example 2. Chemical Formula E2

[0373] [Chemical Formula E2]

[0374]

[0375] A compound of the above chemical formula E2 was prepared in the same manner as in Manufacturing Example 1, except that (3-(pyridin-4-yl)phenyl)boronic acid was used instead of the above (3-(pyridin-3-yl)phenyl)boronic acid in Manufacturing Example 1.

[0376] MS[M+H] + = 847

[0377] Manufacturing Example 3. Synthesis of Chemical Formula E3

[0378] [Chemical Formula E3]

[0379]

[0380] A compound of the above chemical formula E3 was prepared in the same manner as in Preparation Example 1, except that (4-(pyridin-3-yl)phenyl)boronic acid was used instead of the above (3-(pyridin-3-yl)phenyl)boronic acid in Preparation Example 1.

[0381] MS[M+H] + = 847

[0382] Manufacturing Example 4. Synthesis of Chemical Formula E4

[0383] [Chemical Formula E4]

[0384]

[0385] A compound of the above chemical formula E4 was prepared in the same manner as in Preparation Example 1, except that (2-(pyridin-3-yl)phenyl)boronic acid was used instead of the above (3-(pyridin-3-yl)phenyl)boronic acid in Preparation Example 1.

[0386] MS[M+H] + = 847

[0387] Manufacturing Example 5. Synthesis of Chemical Formula E5

[0388] [Chemical Formula E5]

[0389]

[0390] A compound of the chemical formula E5 was prepared in the same manner as in Preparation Example 1, except that 6,6'-(5'-chloro-[1,1':3',1''-terphenyl]-2,2''-diyl)bis(2,4-diphenyl-1,3,5-triazine) was used instead of the compound 6,6'-(5'-chloro-[1,1':2',1''-terphenyl]-2,3''-diyl)bis(2,4-diphenyl-1,3,5-triazine) in Preparation Example 1.

[0391] MS[M+H] + = 847

[0392] Manufacturing Example 6. Synthesis of Chemical Formula E6

[0393] [Chemical Formula E6]

[0394]

[0395] A compound of the above chemical formula E6 was prepared in the same manner as in Preparation Example 5, except that (3-(pyridin-4-yl)phenyl)boronic acid was used instead of the above (3-(pyridin-3-yl)phenyl)boronic acid in Preparation Example 5.

[0396] MS[M+H] + = 847

[0397] Manufacturing Example 7. Synthesis of Chemical Formula E7

[0398] [Chemical Formula E7]

[0399]

[0400] A compound of the chemical formula E7 was prepared in the same manner as in Preparation Example 1, except that 6,6'-(4'-chloro-[1,1':2',1''-terphenyl]-2,3''-diyl)bis(2,4-diphenyl-1,3,5-triazine) was used instead of the compound 6,6'-(5'-chloro-[1,1':3',1''-terphenyl]-2,2''-diyl)bis(2,4-diphenyl-1,3,5-triazine) in Preparation Example 1.

[0401] MS[M+H] + = 847

[0402] Manufacturing Example 8. Synthesis of Chemical Formula E8

[0403] [Chemical Formula E8]

[0404]

[0405] A compound of the above chemical formula E8 was prepared in the same manner as in Preparation Example 7, except that (2-(pyridin-3-yl)phenyl)boronic acid was used instead of the above (3-(pyridin-3-yl)phenyl)boronic acid in Preparation Example 7.

[0406] MS[M+H] + = 847

[0407] Manufacturing Example 9. Synthesis of Chemical Formula E9

[0408] [Chemical Formula E9]

[0409]

[0410] A compound of the above chemical formula E9 was prepared in the same manner as in Preparation Example 7, except that (2-(pyridin-4-yl)phenyl)boronic acid was used instead of the above (3-(pyridin-3-yl)phenyl)boronic acid in Preparation Example 7.

[0411] MS[M+H] + = 847

[0412] Manufacturing Example 10. Synthesis of Chemical Formula E10

[0413] [Chemical formula E10]

[0414]

[0415] A compound of the chemical formula E10 was prepared in the same manner as in Preparation Example 1, except that 6,6'-(4'-chloro-[1,1':2',1''-terphenyl]-2,4''-diyl)bis(2,4-diphenyl-1,3,5-triazine) was used instead of the compound 6,6'-(5'-chloro-[1,1':3',1''-terphenyl]-2,2''-diyl)bis(2,4-diphenyl-1,3,5-triazine) in Preparation Example 1.

[0416] MS[M+H] + = 847

[0417] Manufacturing Example 11. Synthesis of Chemical Formula E11

[0418] [Chemical Formula E11]

[0419]

[0420] A compound of the above chemical formula E11 was prepared in the same manner as in Preparation Example 10, except that (3-(pyridin-4-yl)phenyl)boronic acid was used instead of the above (3-(pyridin-3-yl)phenyl)boronic acid in Preparation Example 10.

[0421] MS[M+H] + = 847

[0422] Manufacturing Example 12. Synthesis of Chemical Formula E12

[0423] [Chemical formula E12]

[0424]

[0425] A compound of the above chemical formula E12 was prepared in the same manner as in Preparation Example 11, except that (2-(pyridin-4-yl)phenyl)boronic acid was used instead of the above (3-(pyridin-3-yl)phenyl)boronic acid in Preparation Example 10.

[0426] MS[M+H] + = 847

[0427] Manufacturing Example 13. Synthesis of Chemical Formula E13

[0428] [Chemical Formula E13]

[0429]

[0430] A compound of the chemical formula E13 was prepared in the same manner as in Preparation Example 1, except that 6,6'-(3'-chloro-[1,1':4',1''-terphenyl]-2,3''-diyl)bis(2,4-diphenyl-1,3,5-triazine) was used instead of the compound 6,6'-(5'-chloro-[1,1':3',1''-terphenyl]-2,2''-diyl)bis(2,4-diphenyl-1,3,5-triazine) in Preparation Example 1.

[0431] MS[M+H] + = 847

[0432] Manufacturing Example 14. Synthesis of Chemical Formula E14

[0433] [Chemical formula E14]

[0434]

[0435] A compound of the above chemical formula E14 was prepared in the same manner as in Preparation Example 13, except that 3-(pyridin-4-yl)phenyl)boronic acid was used instead of the above (3-(pyridin-3-yl)phenyl)boronic acid in Preparation Example 13.

[0436] MS[M+H] + = 847

[0437] Manufacturing Example 15. Synthesis of Chemical Formula E15

[0438] [Chemical formula E15]

[0439]

[0440] A compound of the chemical formula E15 was prepared in the same manner as in Preparation Example 1, except that 6,6'-(3'-chloro-[1,1':2',1''-terphenyl]-3,3''-diyl)bis(2,4-diphenyl-1,3,5-triazine) was used instead of the compound 6,6'-(5'-chloro-[1,1':3',1''-terphenyl]-2,2''-diyl)bis(2,4-diphenyl-1,3,5-triazine) in Preparation Example 1.

[0441] MS[M+H] + = 847

[0442] Manufacturing Example 16. Synthesis of Chemical Formula E16

[0443] [Chemical formula E16]

[0444]

[0445] A compound of the above chemical formula E16 was prepared in the same manner as in Preparation Example 15, except that 3-(pyridin-4-yl)phenyl)boronic acid was used instead of the above-mentioned (3-(pyridin-3-yl)phenyl)boronic acid in Preparation Example 15.

[0446] MS[M+H] + = 847

[0447] Manufacturing Example 17. Synthesis of Chemical Formula E17

[0448] [Chemical formula E17]

[0449]

[0450] A compound of the chemical formula E17 was prepared in the same manner as in Preparation Example 1, except that 6,6'-(4'-chloro-[1,1':3',1''-terphenyl]-2,3''-diyl)bis(2,4-diphenyl-1,3,5-triazine) was used instead of the compound 6,6'-(5'-chloro-[1,1':3',1''-terphenyl]-2,2''-diyl)bis(2,4-diphenyl-1,3,5-triazine) in Preparation Example 1.

[0451] MS[M+H] + = 847

[0452] Manufacturing Example 18. Synthesis of Chemical Formula E18

[0453] [Chemical formula E18]

[0454]

[0455] A compound of the above chemical formula E18 was prepared in the same manner as in Preparation Example 17, except that (3-(pyridin-4-yl)phenyl)boronic acid was used instead of the compound (3-(pyridin-3-yl)phenyl)boronic acid in Preparation Example 17.

[0456] MS[M+H] + = 847

[0457] Manufacturing Example 19. Synthesis of Chemical Formula E19

[0458] [Chemical formula E19]

[0459]

[0460] A compound of the above chemical formula E19 was prepared in the same manner as in Preparation Example 17, except that (2-(pyridin-3-yl)phenyl)boronic acid was used instead of the compound (3-(pyridin-3-yl)phenyl)boronic acid in Preparation Example 17.

[0461] MS[M+H] + = 847

[0462] Manufacturing Example 20. Synthesis of Chemical Formula E20

[0463] [Chemical formula E20]

[0464]

[0465] A compound of the chemical formula E20 was prepared in the same manner as in Preparation Example 1, except that 6,6'-(2'-chloro-[1,1':3',1''-terphenyl]-3,3''-diyl)bis(2,4-diphenyl-1,3,5-triazine) was used instead of the compound 6,6'-(5'-chloro-[1,1':3',1''-terphenyl]-2,2''-diyl)bis(2,4-diphenyl-1,3,5-triazine) in Preparation Example 1.

[0466] MS[M+H] + = 847

[0467] Manufacturing Example 21. Synthesis of Chemical Formula E21

[0468] [Chemical formula E21]

[0469]

[0470] A compound of the above chemical formula E21 was prepared in the same manner as in Preparation Example 20, except that (3-(pyridin-4-yl)phenyl)boronic acid was used instead of the compound (3-(pyridin-3-yl)phenyl)boronic acid in Preparation Example 20.

[0471] MS[M+H] + = 847

[0472] Manufacturing Example 22. Synthesis of Chemical Formula E22

[0473] [Chemical formula E22]

[0474]

[0475] A compound of the chemical formula E22 was prepared in the same manner as in Preparation Example 1, except that 6,6'-(5'-chloro-[1,1':3',1''-terphenyl]-2,2''-diyl)bis(2,4-diphenyl-1,3,5-triazine) was replaced with 6,6'-(5'-chloro-[1,1':3',1''-terphenyl]-2,2''-diyl)bis(2,4-diphenylpyrimidine).

[0476] MS[M+H] + = 845

[0477] Manufacturing Example 23. Synthesis of Chemical Formula E23

[0478] [Chemical formula E23]

[0479]

[0480] A compound of the chemical formula E23 was prepared in the same manner as in Preparation Example 1, except that 6,6'-(5'-chloro-[1,1':3',1''-terphenyl]-2,2''-diyl)bis(2,4-diphenyl-1,3,5-triazine) was replaced with 6,6'-(5'-chloro-[1,1':2',1''-terphenyl]-2,3''-diyl)bis(2,4-diphenylpyrimidine).

[0481] MS[M+H] + = 845

[0482] Manufacturing Example 24. Synthesis of Chemical Formula E24

[0483] [Chemical formula E24]

[0484]

[0485] A compound of the chemical formula E24 was prepared in the same manner as in Preparation Example 1, except that 6,6'-(4'-chloro-[1,1':2',1''-terphenyl]-2,3''-diyl)bis(2,4-diphenylpyrimidine) was used instead of the compound 6,6'-(5'-chloro-[1,1':3',1''-terphenyl]-2,2''-diyl)bis(2,4-diphenyl-1,3,5-triazine) in Preparation Example 1.

[0486] MS[M+H] + = 845

[0487] Manufacturing Example 25 Synthesis of Chemical Formula E25

[0488] [Chemical formula E25]

[0489]

[0490] In Preparation Example 1, 2-(6'-chloro-3''-(2,6-diphenylpyrimidin-4-yl)-[1,1':2',1''-terphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine was used instead of the compound 6,6'-(5'-chloro-[1,1':3',1''-terphenyl]-2,2''-diyl)bis(2,4-diphenyl-1,3,5-triazine), and (2-(pyridin-2-yl)phenyl)boronic acid was used instead of (3-(pyridin-3-yl)phenyl)boronic acid, and the compound of the chemical formula E25 was prepared in the same manner as in Preparation Example 1.

[0491] MS[M+H] + = 845

[0492] Example 1-1

[0493] A glass substrate coated with a 1,000 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 secondarily filtered through 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.

[0494] On the ITO transparent electrode prepared in this way, a hole injection layer was formed by thermally vacuum depositing the compounds HI1 and HI2 below at a ratio of 98:2 (molar ratio) to a thickness of 100 Å. On the hole injection layer, a compound represented by the chemical formula HT1 (1150 Å) was vacuum deposited to form a hole transport layer. Subsequently, an electron blocking layer was formed by vacuum depositing a compound EB1 on the hole transport layer to a film thickness of 50 Å. Subsequently, a light emitting layer was formed by vacuum depositing a compound represented by the chemical formula BH below and a compound represented by the chemical formula BD below at a weight ratio of 50:1 to a film thickness of 200 Å on the electron blocking layer. A hole blocking layer was formed by vacuum depositing a compound represented by the chemical formula HB1 below at a film thickness of 50 Å on the light emitting layer. Next, a compound represented by the following chemical formula E1 and a compound represented by the following chemical formula LiQ were vacuum-deposited at a weight ratio of 1:1 on the hole-blocking layer to form an electron injection and transport layer with a thickness of 30 Å. Lithium fluoride (LiF) was sequentially deposited with a thickness of 12 Å and aluminum was sequentially deposited with a thickness of 1,000 Å on the electron injection and transport layer to form a cathode.

[0495]

[0496] In the above process, the deposition rate of organic materials was maintained at 0.4 to 0.7 Å / sec, lithium fluoride of the cathode was maintained at 0.3 Å / sec, and aluminum was maintained at 2 Å / sec, and the vacuum during deposition was 2ⅹ10 -7 ~ 5ⅹ10 -6 Torr was maintained, and an organic light-emitting device was fabricated.

[0497] Examples 1-2 to 1-24

[0498] An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the compounds described in Table 1 below were used instead of Compound E1 of Example 1.

[0499] Comparative Examples 1-1 to 1-5

[0500] An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the compounds described in Table 1 below were used instead of Compound E1. The compounds ET-1 to ET-5 used in Table 1 below are as follows.

[0501]

[0502] When current was applied to the organic light-emitting devices manufactured by Examples 1-1 to 1-24 and Comparative Examples 1-1 to 1-5, voltage, efficiency, color coordinates, and lifespan were measured, and the results are shown in [Table 1] below. T95 refers to the time required for the luminance to decrease from the initial luminance (1600 nit) to 95%.

[0503] Compound (electron transport layer) voltage (V@20mA / cm 2 )Efficiency (cd / A@20mA / cm 2) Color coordinates (x, y) T95 (hr) Experimental example 1-1 Compound E14.216.13 (0.140, 0.039) 242 Experimental example 1-2 Compound E24.246.010 (0.140, 0.040) 246 Experimental example 1-3 Compound E34.386.03 (0.139, 0.040) 256 Experimental example 1-4 Compound E44.176.16 (0.140, 0.040) 238 Experimental example 1-5 Compound E54.376.07 (0.140, 0.039) 252 Experimental example 1-6 Compound E64.356.08 (0.141, 0.040) 250 Experimental example 1-7 Compound E74.206.16(0.140, 0.039)245Experimental Example 1-8 Compound E84.156.18(0.140, 0.040)240Experimental Example 1-9 Compound E94.146.20(0.139, 0.039)239Experimental Example 1-10 Compound E104.396.02(0.140, 0.040)255Experimental Example 1-11 Compound E114.366.04(0.141, 0.039)253Experimental Example 1-12 Compound E124.306.10(0.140, 0.040)245Experimental Example 1-13 Compound E134.226.18(0.139, 0.041)241Experimental Example 1-14 Compound E144.236.21(0.140, 0.040)239Experimental Example 1-15 Compound E154.126.17(0.140, 0.039)242Experimental Example 1-16 Compound E164.136.15(0.141, 0.039)244Experimental Example 1-17 Compound E174.326.04(0.139, 0.040)256Experimental Example 1-18 Compound E184.356.02(0.139, 0.041)259Experimental Example 1-19 Compound E194.206.09(0.140, 0.040)242Experimental Example 1-20 Compound E204.376.00(0.140, 0.039)261 Experimental Example 1-21 Compound E214.366.01(0.139, 0.039)264 Experimental Example 1-22 Compound E223.986.26(0.140, 0.040)227 Experimental Example 1-23 Compound E234.006.23(0.139, 0.039)232 Experimental Example 1-24 Compound E244.026.21(0.139, 0.040)236 Experimental Example 1-25 Compound E254.106.18(0.140, 0.039)239Comparative example 1-1ET-14.515.65(0.140, 0.040)180Comparative example 1-2ET-24.655.48(0.141, 0.039)198Comparative example 1-3ET-34.715.52(0.140, 0.041)185Comparative example 1-4ET-44.795.15(0.140, 0.040)205Comparative example 1-5ET-54.585.94(0.139, 0.039)210.

[0504] As shown in Table 1 above, in the case of an organic light-emitting device manufactured using the compound of the present invention as an electron transport layer, the organic light-emitting device exhibits excellent characteristics in terms of efficiency, driving voltage, and / or stability.

[0505] Compared to the electron transport layer generally used, the electron injection and mobility were increased by appropriately breaking the conjugation through the appropriate distance between the N-containing ring groups and the ortho-connected linkers, and the electron mobility was controlled by adding a heteroaryl substituent such as pyridine to secure the lifespan, thereby exhibiting low-voltage and high-efficiency characteristics.

[0506] Comparative Example 1-1 used compound ET-1 in which three arylheteroaryl substituents substituted on the phenyl core of the center are of the same type. Comparative Examples 1-2 and 1-3 used compounds ET-2 and ET-3 in which the N-containing heterocycle is polycyclic.

[0507] Comparative Example 1-4 used compound ET-4, which does not contain a phenylene substituted with R11 and does not contain a phenyl group substituted with Ar3 and Ar4.

[0508] Comparative Example 1-5 used compound ET-5, which contains only two N-containing heterocycles.

[0509] Compounds E1 to E25 of the present invention have one of three substituents substituted on the phenyl core different from the other, and the three N-containing heterocycles substituted on the core are monocyclic.

[0510] As can be seen from Table 1 above, Examples 1-1 to 1-25 using compounds E1 to E25 have the characteristics of low voltage, high efficiency, and long life compared to Comparative Examples 1-1 to 1-5.

[0511] Although the preferred embodiment (electron transport layer) of the present invention has been described above, the present invention is not limited thereto, and various modifications can be made within the scope of the claims and the detailed description of the invention, and this also falls within the scope of the invention.

Claims

1. A compound of the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, At least two of X1 to X3 are N, and the rest are CH, At least two of X4 to X6 are N, and the rest are CH, R1 to R11 are the same or different and are each independently hydrogen; deuterium; or cyano group, r10 is 1 or 2, and when said r10 is 2, said two R10s are equal to or different from each other, r11 is an integer from 1 to 4, and when r11 is 2 or more, 2 or more R11 are the same or different, Ar1 to Ar4 are the same or different from each other, and are each independently hydrogen; deuterium; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, ar1 is an integer from 1 to 5, and when ar1 is 2 or more, 2 or more Ar1 are equal to or different from each other, ar2 is an integer from 1 to 5, and when ar2 is 2 or more, 2 or more Ar2 are the same or different from each other, ar3 is an integer from 1 to 5, and when ar3 is 2 or more, 2 or more Ar3 are the same or different from each other, ar4 is an integer from 1 to 5, and when ar4 is 2 or more, 2 or more Ar4 are the same as or different from each other, One or two of Y1 to Y5 are N, and the others are each independently CR'1, R'1 is hydrogen; deuterium; a cyano group; or a substituted or unsubstituted alkyl group, or is bonded to an adjacent group to form a substituted or unsubstituted aromatic hydrocarbon ring.

2. In claim 1, the compound wherein the chemical formula 1 is any one of the following chemical formulas 1-1 to 1-5: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] [Chemical Formula 1-5] In the above chemical formulas 1-1 to 1-5, The definitions of X1 to X6, Y1 to Y5, R1 to R9, R11, r11, Ar1 to Ar4 and ar1 to ar4 are the same as those defined in the above chemical formula 1, R101 to R104 are the same or different, and each independently represent hydrogen; deuterium; or cyano group.

3. In claim 1, the compound wherein the chemical formula 1 is any one of the following chemical formulas 1-6 to 1-9: [Chemical Formula 1-6] [Chemical Formula 1-7] [Chemical Formula 1-8] [Chemical Formula 1-9] In the above chemical formulas 1-6 to 1-9, The definitions of X1 to X6, Y1 to Y5, R1 to R11, r10, r11, Ar1 to Ar4 and ar1 to ar4 are the same as those defined in the above chemical formula 1.

4. In claim 1, the chemical formula 1 A compound having one of the following structural formulas: In the above structure, * is a site that is bonded to the above chemical formula 1, R'11 to R'15 are the same or different, and each independently represents hydrogen; deuterium; a cyano group; or a substituted or unsubstituted alkyl group, or combine with an adjacent group to form a substituted or unsubstituted aromatic hydrocarbon ring.

5. In claim 1, the chemical formula 1 and are different compounds: * is the site that binds to chemical formula 1, The definitions of X1 to X6, Ar1 to Ar4 and ar1 to ar4 are the same as those defined in the above chemical formula 1.

6. In claim 1, the chemical formula 1 and are compounds that are identical to each other: * is the site that binds to chemical formula 1, The definitions of X1 to X6, Ar1 to Ar4 and ar1 to ar4 are the same as those defined in the above chemical formula 1.

7. In claim 1, Ar1 to Ar4 are the same as or different from each other, and are each independently hydrogen; deuterium; a cyano group; 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 monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms. A compound wherein the above R'1 is hydrogen; deuterium; a cyano group; or a straight or branched alkyl group having 1 to 30 carbon atoms, or is bonded to an adjacent group to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms.

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

9. 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 8.

10. An organic light-emitting device according to claim 9, wherein 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.

11. An organic light-emitting device according to claim 9, wherein the organic layer includes a hole-blocking layer, and the hole-blocking layer includes the compound.

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