Compound and organic light emitting device comprising same

Abstract

The present specification relates to a compound of Formula 1 and an organic light-emitting device containing the same.

Description

Technology Field

[0001] This specification relates to a compound and an organic light-emitting device containing the same. Background Technology

[0002] Generally, organic light emission refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic light-emitting devices (OLEDs) that utilize this phenomenon typically have a structure comprising an anode, a cathode, and an organic layer between them. Here, the organic layer is often composed of a multilayer structure made of different materials to enhance the efficiency and stability of the OLED; for example, it may consist of a hole injection layer, a hole transport layer, an emissive layer, an electron transport layer, and an electron injection layer. In the structure of such an OLED, when a voltage is applied between the two electrodes, holes are injected into the organic layer from the anode and electrons from the cathode. When the injected holes and electrons meet, an exciton is formed, and light is emitted when this exciton returns to the ground state.

[0003] The development of new materials for organic light-emitting devices as described above is continuously required. Prior art literature

[0004] Korean Patent Publication No. 2000-0051826 The problem to be solved

[0005] The present specification provides a compound and an organic light-emitting device comprising the same. means of solving the problem

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

[0007] [Chemical Formula 1]

[0008]

[0009] In the above chemical formula 1,

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

[0011] L1 and L2 are the same or different from each other and are each independently directly bonded; or are substituted or unsubstituted arylene groups, and

[0012] R1 to R3 are the same or different from each other, and each is independently a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, and

[0013] G1 to G5 are the same or different from one another, and each is independently hydrogen; deuterium; or a substituted or unsubstituted aryl group, and

[0014] g1 to g4 are each integers from 0 to 4, and

[0015] g5 is an integer from 0 to 8, and

[0016] If the above g1 is 2 or more, the above 2 or more G1s are the same or different from each other, and

[0017] If the above g2 is 2 or more, the above 2 or more G2s are the same or different from each other, and

[0018] If the above g3 is 2 or more, the above 2 or more G3s are the same or different from each other, and

[0019] If the above g4 is 2 or more, the above 2 or more G4s are the same or different from each other, and

[0020] If the above g5 is 2 or more, the above 2 or more G5s are the same or different from each other, and

[0021] 0 ≤ g1 + g2 ≤ 7.

[0022] In addition, one embodiment of the present specification provides an organic light-emitting device comprising a first electrode; a second electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers comprise the aforementioned compound. Effects of the invention

[0023] The compounds described herein may be used as materials for the organic layer of an organic light-emitting device. Compounds according to at least one embodiment of this specification may improve efficiency, lower driving voltage, and / or lifespan characteristics in an organic light-emitting device. In particular, the compounds described herein may be used as materials for an emissive layer, electron injection, electron transport, electron injection and electron transport, or hole blocking. Furthermore, compared to conventional organic light-emitting devices, they provide the effects of lower driving voltage, high efficiency, and / or long lifespan. Brief explanation of the drawing

[0024] FIGS. 1 and 2 illustrate examples of organic light-emitting devices according to one embodiment of the present specification. Figure 3 is an MS graph of compound A. Specific details for implementing the invention

[0025] The present specification will be described in more detail below.

[0026] The present specification provides a compound of the above chemical formula 1.

[0027] According to one embodiment of the present specification, Formula 1 is a compound in which a carbazole group substituted or unsubstituted with a spirofluorene-9,9'-xanthen core and a single-ring N-containing six-membered heterocyclic ring substituted with -L3-SiR1R2R3 are bonded. The bulky silyl group has a structural feature that stabilizes the excited and polaronic states of Formula 1 by participating in the conjugation system through a hyperconjugation effect. Additionally, by including a carbazole structure, the LUMO energy level of the compound can be increased, thereby preventing host-guest electrostatic coupling in the organic layer of an organic light-emitting device containing it. Therefore, Formula 1 can be incorporated into the organic layer of an organic light-emitting device to enable improved efficiency, lower driving voltage, and improved lifespan characteristics.

[0028] Examples of substituents in this specification are described below, but are not limited thereto.

[0029] In this specification, refers to the connected part.

[0030] The term "substitution" above means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the substitution site is not limited to the site where the hydrogen atom is substituted, that is, any site where a substituent can be substituted, and in the case of two or more substitutions, the two or more substituents may be the same or different from each other.

[0031] In this specification, the term “substituted or unsubstituted” means that it is 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; condensed ring group of aromatic hydrocarbon ring and aliphatic hydrocarbon ring; and heteroaryl group, or is substituted with a substituent in which two or more of the exemplified substituents are connected, or has no substituents.

[0032] In this specification, the connection of two or more substituents means that a 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 It can be a substituent. In addition, the connection of three substituents includes not only the consecutive connection of (substituent 1)-(substituent 2)-(substituent 3), but also the connection of (substituent 2) and (substituent 3) to (substituent 1). For example, a phenyl group, a naphthyl group, and an isopropyl group are connected, , or It can be a substituent. The aforementioned definition applies equally to the connection of 4 or more substituents.

[0033] In this specification, examples of halogen groups include fluoro groups, chloro groups, bromo groups, or iodo groups.

[0034] In the present specification, the alkyl group may be a straight chain or a branched chain, 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, There are, but are not limited to, 2,2-dimethylheptyl groups, 1-ethyl-propyl groups, 1,1-dimethyl-propyl groups, isohexyl groups, 2-methylpentyl groups, 4-methylhexyl groups, 5-methylhexyl groups.

[0035] In the present specification, the cycloalkyl group is not particularly limited, but is preferably 3 to 30 carbon atoms. Specifically, it 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, etc.

[0036] In the present specification, the alkoxy group may be a straight chain, a branched chain, or a cyclic chain. The number of carbon atoms in the alkoxy group is not particularly limited, but it is preferred to have 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.

[0037] In the present specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples include, butanely, vinyl group, 1-propenyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 3-methyl-1-butenyl group, 1,3-butadienyl group, allyl group, 1-phenylvinyl-1-yl group, 2-phenylvinyl-1-yl group, 2,2-diphenylvinyl-1-yl group, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl group, 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, stilbenyl group, styrenyl group, etc., but are not limited thereto.

[0038] In this specification, a haloalkyl group means that at least one halogen group is substituted for the hydrogen of the alkyl group in the definition of the alkyl group.

[0039] In the present specification, the aryl group is not particularly limited, but is preferably 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.

[0040] When the above aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but it is preferable that the number of carbon atoms be 6 to 30. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.

[0041] When the above aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but it is preferable that the number of carbon atoms be 10 to 30. Specifically, the polycyclic aryl group may be a naphthyl group, anthracene group, phenanthrene group, triphenylene group, pyrene group, phenalene group, perylene group, chrysene group, fluorene group, etc., but is not limited thereto.

[0042] In the present specification, the fluorene group may be substituted, and adjacent groups may combine with each other to form a ring.

[0043] Examples of the above fluorene group include , , , , , , and There are, but are not limited to, the following.

[0044] In this specification, "adjacent" groups may mean a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent located closest to the atom on which the substituent is substituted, or another substituent substituted on the atom on which the substituent is substituted. For example, two substituents substituted at the ortho position in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring may be interpreted as "adjacent" groups to each other.

[0045] In the present specification, the heteroaryl group comprises one or more non-carbon atoms or heteroatoms, and specifically, the heteroatoms may comprise one or more atoms selected from the group consisting of O, N, Se, and S. The number of carbon atoms is not particularly limited, but it is preferable that the number of carbon atoms be 2 to 30, and the heteroaryl group may be monocyclic or polycyclic. Examples of heteroaryl groups include thiophene, furan, pyrrole, imidazole, thiazole, oxazole, oxadiazole, pyridine, bipyridine, pyrimidine, triazine, triazole, acridine, pyridazine, pyrazine, quinoline, quinazolin, quinoxaline, phthalazine, pyridopyrimidine, pyridopyrazine, pyrazinopyrazine, isoquinoline, indole, carbazole, benzoxazole, benzimidazole, benzothiazole, benzocarbazole, benzothiophen, dibenzothiophen, benzofuran, phenanthridine, phenanthroline, isooxazole, and thiadiazole. Dibenzofuran group, dibenzosilol group, phenoxanthine group (phenoxathiine), phenoxazine group, phenothiazine group, dihydroindenocarbazole group, spiroflurenxanthen group, and spiroflurentioxanthen group are included, but are not limited to these.

[0046] In this 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 an example of the alkyl group described above, among the arylsilyl groups, the aryl group may be an example of the aryl group described above, and among the heteroarylsilyl groups, the heteroaryl group may be an example of the heteroaryl group described above.

[0047] In this specification, the boron group is -BR 100 R 101 It may be, and the above R 100 and R 101The boron groups may be the same or different and each independently selected from the group consisting of hydrogen; deuterium; halogen; 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 groups specifically include, but are not limited to, dimethylboron groups, diethylboron groups, t-butylmethylboron groups, diphenylboron groups, etc.

[0048] In this specification, the amine group may be selected from the group consisting of -NH2, alkylamine group, N-alkylarylamine group, arylamine group, N-arylheteroarylamine group, N-alkylheteroarylamine group, and heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of amine groups include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 9-methyl-anthracenylamine group, diphenylamine group, ditolylamine group, N-phenyltolylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, and N-biphenylnaphthylamine group; There are, but are not limited to, N-naphthylfluorenylamine groups, N-phenylphenanthrenylamine groups, N-biphenylphenanthrenylamine groups, N-phenylfluorenylamine groups, N-phenylterphenylamine groups, N-phenanthrenylfluorenylamine groups, N-biphenylfluorenylamine groups.

[0049] In this specification, an N-alkylarylamine group refers to an amine group in which an alkyl group and an aryl group are substituted on N of the amine group. The alkyl group and the aryl group in the N-alkylarylamine group are the same as the examples of alkyl and aryl groups described above.

[0050] In this specification, the N-arylheteroarylamine group refers to an amine group in which an aryl group and a heteroaryl group are substituted on N of the amine group. The aryl group and the heteroaryl group in the N-arylheteroarylamine group are the same as the examples of the aryl group and the heteroaryl group described above.

[0051] In this specification, an N-alkylheteroarylamine group refers to an amine group in which an alkyl group and a heteroaryl group are substituted on N of the amine group. The alkyl group and the heteroaryl group in the N-alkylheteroarylamine group are the same as the examples of the alkyl group and the heteroaryl group described above.

[0052] In this specification, examples of arylamine groups include substituted or unsubstituted monoarylamine groups or substituted or unsubstituted diarylamine groups. An arylamine group comprising 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 among the arylamine groups may be selected from the examples of aryl groups described above.

[0053] In this specification, examples of heteroarylamine groups include substituted or unsubstituted monoheteroarylamine groups or substituted or unsubstituted diheteroarylamine groups. A heteroarylamine group comprising two or more heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group simultaneously. For example, the heteroaryl group among the heteroarylamine groups may be selected from the examples of heteroaryl groups described above.

[0054] In this specification, the hydrocarbon ring may be an aromatic hydrocarbon ring; an aliphatic hydrocarbon ring; or a condensed ring of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, wherein the description of the aryl group described above may apply to the aromatic hydrocarbon ring, and the description of the cycloalkyl group described above may apply to the aliphatic hydrocarbon ring. Furthermore, the condensed ring of the aromatic hydrocarbon ring and the aliphatic hydrocarbon ring may have a structure in which the aryl group and the cycloalkyl group described above are condensed together.

[0055] In this specification, an arylene group refers to a group having two binding sites to an aryl group, i.e., a divalent group. Except for the fact that each of these is a divalent group, the description of the aryl group described above may apply.

[0056] Unless otherwise defined in this specification, all technical and scientific terms used herein have the same meaning as commonly understood by those skilled in the art to which the present invention pertains. Methods and materials similar or equivalent to those described herein may be used in the practice or testing of embodiments of the present invention, but suitable methods and materials are described below. All publications, patent applications, patents, and other references mentioned herein are incorporated herein by reference in their entirety, and in the event of conflict, unless a specific passage is not mentioned, this specification, including definitions, shall prevail. Furthermore, materials, methods, and embodiments are merely illustrative and are not intended to be limiting.

[0057] The compound of Chemical Formula 1 above will be described in detail below.

[0058] According to one embodiment of the present specification, the formula 1 is any one of the following formulas 1-1 to 1-4.

[0059] [Chemical Formula 1-1]

[0060]

[0061] [Chemical Formula 1-2]

[0062]

[0063] [Chemical Formula 1-3]

[0064]

[0065] [Chemical Formula 1-4]

[0066]

[0067] In the above chemical formulas 1-1 to 1-4,

[0068] The definitions of X1 to X3, L1, L2, R1 to R3, G1 to G5, and g2 to g5 are the same as those defined in Chemical Formula 1 above, and

[0069] g'1 is an integer from 0 to 3, and if g'1 is 2 or more, the 2 or more G1s are the same or different from each other.

[0070] According to one embodiment of the present specification, the formula 1 is any one of the following formulas 1-5 to 1-8.

[0071] [Chemical Formula 1-5]

[0072]

[0073] [Chemical Formula 1-6]

[0074]

[0075] [Chemical Formula 1-7]

[0076]

[0077] [Chemical Formula 1-8]

[0078]

[0079] In the above chemical formulas 1-5 to 1-8,

[0080] The definitions of X1 to X3, L1, L2, R1 to R3, G1 to G5, g1 and g3 to g5 are the same as those defined in Chemical Formula 1 above, and

[0081] g'2 is an integer from 0 to 3, and if g'2 is 2 or more, the 2 or more G2s are the same or different from each other.

[0082] According to one embodiment of the present specification, at least one of X1 to X3 is N, and the remainder is CH.

[0083] According to one embodiment of the present specification, any one of X1 to X3 is N, and the rest are CH.

[0084] According to one embodiment of the present specification, any two of X1 to X3 are N, and the remainder is CH.

[0085] According to one embodiment of the present specification, X1 to X3 are N.

[0086] According to one embodiment of the present specification, X1 is N, and X2 and X3 are CH.

[0087] According to one embodiment of the present specification, X2 is N, and X1 and X3 are CH.

[0088] According to one embodiment of the present specification, X3 is N, and X1 and X2 are CH.

[0089] According to one embodiment of the present specification, X1 and X2 are N, and X3 is CH.

[0090] According to one embodiment of the present specification, X1 and X3 are N, and X2 is CH.

[0091] According to one embodiment of the present specification, X2 and X3 are N, and X1 is CH.

[0092] According to one embodiment of the present specification, the formula 1 is any one of the following formulas 2 to 6.

[0093] [Chemical Formula 2]

[0094]

[0095] [Chemical Formula 3]

[0096]

[0097] [Chemical Formula 4]

[0098]

[0099] [Chemical Formula 5]

[0100]

[0101] [Chemical Formula 6]

[0102]

[0103] In the above chemical formulas 2 to 6,

[0104] The definitions of L1, L2, R1 to R3, G1 to G5, and g1 to g5 are the same as those defined in Chemical Formula 1 above.

[0105] According to one embodiment of the present specification, L1 and L2 are the same or different from each other and each independently is any one of the following structures.

[0106]

[0107]

[0108] In the above structure,

[0109] D is deuterium, and

[0110] Q1 and Q2 are the same or different from each other, and each is independently a deuterium; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms, and the dotted line indicates a connecting part.

[0111] According to one embodiment of the present specification, Q1 and Q2 are the same or different from each other and are each independently deuterium; a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a straight-chain or branched-chain alkyl group having 1 to 20 carbon atoms.

[0112] According to one embodiment of the present specification, Q1 and Q2 are the same or different from each other and are each independently deuterium; a phenyl group; or a methyl group.

[0113] According to one embodiment of the present specification, G1 to G5 are the same or different from each other and each independently is any one of the following structures.

[0114]

[0115]

[0116] In the above structure,

[0117] H is hydrogen, D is deuterium, and,

[0118] Q3 and Q4 are the same or different from each other, and each is independently a deuterium; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms, and the dotted line indicates a connecting part.

[0119] According to one embodiment of the present specification, Q3 and Q4 are the same or different from each other and are each independently deuterium; a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a straight-chain or branched-chain alkyl group having 1 to 20 carbon atoms.

[0120] According to one embodiment of the present specification, Q3 and Q4 are the same or different from each other and are each independently deuterium; a phenyl group; or a methyl group.

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

[0122] The above L1 is a direct connection, and

[0123] The above L2 is a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms that is substituted or unsubstituted with deuterium, and

[0124] The above R1 to R3 are the same or different from each other and are each independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is substituted or unsubstituted with deuterium, and

[0125] The above G1 to G4 are the same or different from each other, and each is independently hydrogen; or deuterium,

[0126] The above G5 is hydrogen; deuterium; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium.

[0127] According to one embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently directly bonded; or are a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0128] According to one embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently directly bonded; or are a single or polycyclic arylene group having 6 to 20 carbon atoms that is substituted or unsubstituted.

[0129] According to one embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently directly bonded; or are a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 10 carbon atoms.

[0130] According to one embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently directly bonded; or are a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms that is substituted or unsubstituted with deuterium.

[0131] According to one embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently directly bonded; or are a single or polycyclic arylene group having 6 to 20 carbon atoms substituted or unsubstituted with deuterium.

[0132] According to one embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently directly bonded; or are a monocyclic or polycyclic arylene group having 6 to 10 carbon atoms that is substituted or unsubstituted with deuterium.

[0133] According to one embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently directly bonded; or are phenylene groups substituted or unsubstituted with deuterium.

[0134] According to one embodiment of the present specification, L1 is a direct connection.

[0135] According to one embodiment of the present specification, L2 is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0136] According to one embodiment of the present specification, L2 is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

[0137] According to one embodiment of the present specification, L2 is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 10 carbon atoms.

[0138] According to one embodiment of the present specification, L2 is a single or polycyclic arylene group having 6 to 30 carbon atoms that is substituted or unsubstituted with deuterium.

[0139] According to one embodiment of the present specification, L2 is a single or polycyclic arylene group having 6 to 20 carbon atoms that is substituted or unsubstituted with deuterium.

[0140] According to one embodiment of the present specification, L2 is a single or polycyclic arylene group having 6 to 10 carbon atoms that is substituted or unsubstituted with deuterium.

[0141] According to one embodiment of the present specification, L2 is a phenylene group substituted or unsubstituted with deuterium.

[0142] According to one embodiment of the present specification, R1 to R3 are the same or different from each other and are each independently substituted or unsubstituted monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms.

[0143] According to one embodiment of the present specification, R1 to R3 are the same or different from each other and are each independently substituted or unsubstituted monocyclic or polycyclic aryl groups having 6 to 20 carbon atoms.

[0144] According to one embodiment of the present specification, R1 to R3 are the same or different from each other and are each independently substituted or unsubstituted monocyclic or polycyclic aryl groups having 6 to 10 carbon atoms.

[0145] According to one embodiment of the present specification, R1 to R3 are the same or different from each other and are each independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is substituted or unsubstituted with deuterium.

[0146] According to one embodiment of the present specification, R1 to R3 are the same or different from each other and are each independently a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms that is substituted or unsubstituted with deuterium.

[0147] According to one embodiment of the present specification, R1 to R3 are the same or different from each other and are each independently a monocyclic or polycyclic aryl group having 6 to 10 carbon atoms that is substituted or unsubstituted with deuterium.

[0148] According to one embodiment of the present specification, R1 to R3 are the same or different from each other and are each independently a phenyl group substituted or unsubstituted with deuterium.

[0149] According to one embodiment of the present specification, G1 to G4 are the same or different from one another and are each independently hydrogen; or deuterium.

[0150] According to one embodiment of the present specification, G1 to G4 are hydrogen.

[0151] According to one embodiment of the present specification, G1 to G4 are deuterium.

[0152] According to one embodiment of the present specification, G5 is hydrogen; deuterium; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a monocyclic or polycyclic group.

[0153] According to one embodiment of the present specification, G5 is hydrogen; deuterium; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a monocyclic or polycyclic group.

[0154] According to one embodiment of the present specification, G5 is hydrogen; deuterium; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 10 carbon atoms.

[0155] According to one embodiment of the present specification, the G5 is hydrogen; deuterium; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium.

[0156] According to one embodiment of the present specification, G5 is hydrogen; deuterium; or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms substituted or unsubstituted with deuterium.

[0157] According to one embodiment of the present specification, the G5 is hydrogen; deuterium; or a monocyclic or polycyclic aryl group having 6 to 10 carbon atoms substituted or unsubstituted with deuterium.

[0158] According to one embodiment of the present specification, G5 is hydrogen; deuterium; or a phenyl group substituted or unsubstituted with deuterium.

[0159] According to one embodiment of the present specification, the formula 1 comprises at least one deuterium.

[0160] According to one embodiment of the present specification, the meaning of “at least one comprising deuterium” is that one or more of the hydrogens at substitutable positions are substituted with deuterium or substituted with a substituent that is substituted with deuterium. The substituent includes the substituent defined in “substituted or unsubstituted”.

[0161] According to one embodiment of the present specification, the deuterium substitution rate of Formula 1 is 0% to 100%.

[0162] According to one embodiment of the present specification, the deuterium substitution rate of Formula 1 is 0.01% to 100%.

[0163] According to one embodiment of the present specification, the deuterium substitution rate of Formula 1 is 0.1% to 100%.

[0164] According to one embodiment of the present specification, the deuterium substitution rate of Formula 1 is 1% to 100%.

[0165] According to one embodiment of the present specification, the deuterium substitution rate of Formula 1 is 40% to 99%.

[0166] According to one embodiment of the present specification, when the above formula 1 includes deuterium, the following effects are achieved. Specifically, physicochemical properties such as chemical bond lengths associated with deuterium differ from those of hydrogen, and the elongation amplitude of CD bonds is smaller than that of CH bonds, so the van der Waals radius of deuterium is smaller than that of hydrogen, and generally, CD bonds can be shown to be shorter and stronger than CH bonds. Therefore, when hydrogen at a substitutable position in the above formula 1 is substituted with deuterium, the ground state energy is lowered, and as the bond length between deuterium and carbon is shortened, the molecular hardcore volume is reduced, and accordingly, electrical polarizability can be reduced, and by weakening intermolecular interactions, the thin film volume can be increased. In addition, these characteristics can lower the crystallinity of the thin film, i.e., create an amorphous state, which can generally be effective in increasing the lifespan and driving characteristics of organic light-emitting diodes, and can improve heat resistance compared to conventional organic light-emitting diodes.

[0167] In this specification, "containing deuterium," "deuterated," or "deuterated" means that hydrogen at a substitutable position of a compound is substituted with deuterium.

[0168] In this specification, "deuteriumized" means a compound or group in which all hydrogens in the molecule are substituted with deuterium, and has the same meaning as "100% deuteriumized."

[0169] In this specification, "X% deuterated," "degree of deuteration X%," or "deuterium substitution rate X%" means that X% of the hydrogens at substitutable positions in the structure are replaced with deuterium. For example, if the structure is dibenzofuran, "25% deuterated" of the dibenzofuran, "degree of deuteration 25%" of the dibenzofuran, or "deuterium substitution rate 25%" of the dibenzofuran means that 2 of the 8 hydrogens at substitutable positions of the dibenzofuran are replaced with deuterium.

[0170] In this specification, "deuterium degree" or "deuterium substitution rate" refers to nuclear magnetic resonance spectroscopy ( 1 It can be confirmed by known methods such as ¹H NMR), TLC / MS (Thin-Layer Chromatography / Mass Spectrometry), or GC / MS (Gas Chromatography / Mass Spectrometry).

[0171] Specifically, nuclear magnetic resonance spectroscopy ( 1 When analyzing "deuteration" or "deuteration substitution rate" using ¹H NMR, DMF (dimethylformamide) is added as an internal standard, 1 Through the integration ratio on the ¹H NMR, the degree of deuteration or deuterium substitution rate can be calculated from the total integrated amount of the peak.

[0172] In addition, when analyzing the "deuteration" or "deuteration rate" through TLC / MS (Thin-Layer Chromatography / Mass Spectrometry), the substitution rate can be calculated based on the maximum value (median) of the distribution of molecular weights at the end of the reaction. For example, when analyzing the deuteration of the following compound A, the molecular weight of the following starting material is 506, and the maximum value (median) of the molecular weight of the following compound A in the MS graph of Fig. 3 is 527. Since 21 of the 26 hydrogens at substitutable positions of the following starting material were substituted with deuteration, it can be calculated that approximately 81% of the hydrogens were deuterated.

[0173]

[0174] [Starting Material] [Compound A]

[0175] In this specification, D means deuterium.

[0176] According to one embodiment of the present specification, the chemical formula 1 is any one of the following compounds.

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186] In the above compound,

[0187] D is deuterium, and

[0188] n is an integer from 0 to 42.

[0189] In addition, the present specification provides an organic light-emitting device comprising the compound described above.

[0190] In this specification, when it is stated that a component is located "on" another component, this includes not only cases where a component is in contact with another component, but also cases where another component exists between the two components.

[0191] In this specification, when a part is described as "comprising" a certain component, this means that, unless specifically stated otherwise, it does not exclude other components but may include additional components.

[0192] In this specification, the term "layer" is used in the sense of a "film" commonly used in the art and refers to a coating that covers a desired 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 equal to the size of the entire device, correspond to the size of a specific functional area, or be as small as a single subpixel.

[0193] In the present specification, the meaning of a specific A substance being included in a B layer includes both i) one or more types of A substances being included in a single B layer and ii) the B layer being composed of one or more layers and A substance being included in one or more layers among the multilayer B layers.

[0194] In the present specification, the meaning that a specific A material is included in a C layer or a D layer is that it is included in at least one of the C layers, ii) included in at least one of the D layers, or iii) included in each of the C layers and the D layers.

[0195] In this specification, n-type refers to a material generally known to be capable of taking electrons from a matrix material (material of an organic layer), and is not limited thereto. That is, n-type can be defined as a material having the characteristic of being able to provide electrons to the LUMO (lowest unoccupied molecular orbital) energy level of the matrix. Conversely, p-type refers to a material that, when forming a layer consisting solely of p-type material, accepts electrons from the HOMO (highest occupied molecular orbital) energy level of the material located in the adjacent cathode direction, thereby generating holes in that material; or, when doping an arbitrary matrix with p-type material, accepts electrons from the HOMO of the matrix material and generates holes in the matrix HOMO by the same amount. To achieve this, when forming a layer consisting solely of p-type material, the closer the HOMO level of the material located in the cathode direction is to the LUMO of the p-type material, the easier it is to steal electrons from the HOMO of the adjacent layer and generate holes in the adjacent layer. Furthermore, when doping an arbitrary matrix with p-type material, the closer the LUMO of the p-type material is to the HOMO of the matrix, the easier it is to steal electrons and generate holes in the matrix.

[0196] The present specification provides an organic light-emitting device comprising: a first electrode; a second electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers comprise a compound of Formula 1.

[0197] The organic layer of the organic light-emitting device of the present specification may be formed as a single layer structure, but may be formed as a multilayer structure in which two or more organic layers are stacked. For example, it may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, etc. However, the structure of the organic light-emitting device is not limited thereto and may include a smaller number of organic layers.

[0198] According to one embodiment of the present specification, the organic layer comprises an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer comprises the compound.

[0199] According to one embodiment of the present specification, the organic layer comprises a hole blocking layer, and the hole blocking layer comprises the compound.

[0200] According to one embodiment of the present specification, the organic layer comprises a hole injection layer, a hole transport layer, or a hole injection and transport layer.

[0201] According to one embodiment of the present specification, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises the compound.

[0202] According to one embodiment of the present specification, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises the compound as a host of the light-emitting layer.

[0203] According to one embodiment of the present specification, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises the compound as an n-type phosphorescent host of the light-emitting layer.

[0204] According to one embodiment of the present specification, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises the compound as a host and further comprises another host.

[0205] According to one embodiment of the present specification, the organic layer comprises a light-emitting layer, the light-emitting layer comprises the compound as a host, and further comprises the host and a dopant.

[0206] According to one embodiment of the present specification, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises the compound as a first host and further comprises a second host.

[0207] According to one embodiment of the present specification, the first host is an n-type phosphorescent host, and the second host is a p-type phosphorescent host.

[0208] According to one embodiment of the present specification, the light-emitting layer comprises a first host and a second host in a weight ratio of 2:8 to 8:2, and the first host is a compound of Formula 1.

[0209] According to one embodiment of the present specification, the light-emitting layer comprises a first host and a second host in a weight ratio of 1:1, and the first host is a compound of Formula 1.

[0210] According to one embodiment of the present specification, the second host is a carbazole-based compound.

[0211] According to one embodiment of the present specification, the second host is a viscarbazole-based compound.

[0212] According to one embodiment of the present specification, the second host is a biscarbazole-based compound substituted with an aryl group.

[0213] According to one embodiment of the present specification, the light-emitting layer further comprises a dopant.

[0214] According to one embodiment of the present specification, the light-emitting layer includes a first host and a second host, and further includes a dopant.

[0215] According to one embodiment of the present specification, the dopant is a phosphorescent dopant.

[0216] According to one embodiment of the present specification, the dopant is included in an amount of 1 to 20 parts by weight per 100 parts by weight of the host.

[0217] According to one embodiment of the present specification, the light-emitting layer comprises a dopant, and the dopant comprises a phosphorescent dopant.

[0218] According to one embodiment of the present specification, the organic layer comprises a light-emitting layer, the light-emitting layer comprises a host and a dopant, the host comprises the compound, and the dopant comprises the phosphorescent dopant.

[0219] According to one embodiment of the present specification, the light-emitting layer is a blue light-emitting layer.

[0220] According to one embodiment of the present specification, the light-emitting layer comprises a host and a dopant in a weight ratio of 99:1 to 1:99. Specifically, it comprises a weight ratio of 99:1 to 50:50, and more specifically, a weight ratio of 99:1 to 95:5.

[0221] When the above-mentioned light-emitting layer emits red light, phosphorescent materials such as PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonate iridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium), and PtOEP(octaethylporphyrin platinum), or fluorescent materials such as Alq3(tris(8-hydroxyquinolino)aluminum) may be used as light-emitting dopants, but are not limited thereto. When the light-emitting layer emits green light, phosphorescent materials such as Ir(ppy)3(fac tris(2-phenylpyridine)iridium) or fluorescent materials such as Alq3(tris(8-hydroxyquinolino)aluminum) may be used as light-emitting dopants, but are not limited thereto. When the light-emitting layer emits blue light, phosphorescent materials such as platinum complex compounds and (4,6-F2ppy)2Irpic, or fluorescent materials such as spiro-DPVBi, spiro-6P, distilbenzene (DSB), distrylarylene (DSA), PFO-based polymers, and PPV-based polymers may be used as light-emitting dopants, but are not limited to these.

[0222] According to one embodiment of the present specification, the dopant is a metal complex compound.

[0223] According to one embodiment of the present specification, the dopant is a platinum complex compound.

[0224] According to one embodiment of the present specification, the dopant is an iridium complex compound.

[0225] According to one embodiment of the present specification, the dopant compound may be selected from the following structural formulas, but is not limited thereto.

[0226]

[0227]

[0228]

[0229]

[0230] According to one embodiment of the present specification, the organic layer includes an electron blocking layer.

[0231] According to one embodiment of the present specification, the organic layer further comprises one or more layers among a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and an electron injection and transport layer.

[0232] According to one embodiment of the present specification, the organic light-emitting device further comprises one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a hole injection and transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, a hole blocking layer, and an electron blocking layer.

[0233] According to one embodiment of the present specification, the organic light-emitting element comprises: a first electrode; a second electrode provided opposite to 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.

[0234] According to one embodiment of the present specification, two or more organic layers may be selected from the group consisting of a hole injection layer, a hole transport layer, a hole injection and transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, a hole blocking layer, and an electron blocking layer.

[0235] 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.

[0236] According to one embodiment of the present specification, the first electrode is an anode or a cathode.

[0237] According to one embodiment of the present specification, the second electrode is a cathode or an anode.

[0238] According to one embodiment of the present specification, the organic light-emitting device may be an organic light-emitting device of a normal type structure in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate.

[0239] 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.

[0240] 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 an organic light-emitting device and are not limited thereto.

[0241] FIG. 1 illustrates the structure of an organic light-emitting device in which a first electrode (2), an organic layer (4), and a second electrode (3) are sequentially stacked on a substrate (1). The compound is included in the organic layer.

[0242] 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 blocking layer (7), a light-emitting layer (8), an electron injection and transport layer (9), and a second electrode (3) are sequentially stacked on a substrate (1). The compound is included in the light-emitting layer (8).

[0243] The organic light-emitting device of the present specification can be manufactured using materials and methods known in the art, except that the light-emitting layer comprises the compound, namely the compound of Formula 1.

[0244] When the above organic light-emitting element includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.

[0245] 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, the device can be manufactured by forming an anode by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate using a physical vapor deposition (PVD) method such as sputtering or electron beam evaporation, forming an organic layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to such a method, an organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.

[0246] In addition, the compound of Chemical Formula 1 can be formed as an organic layer by vacuum deposition as well as by solution coating when manufacturing an organic light-emitting device. Here, solution coating refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited thereto.

[0247] In addition to this method, an organic light-emitting diode can also be fabricated by sequentially depositing an organic layer and an anode material from a cathode material onto a substrate. However, the manufacturing method is not limited to this.

[0248] As for the anode material, a material with a high work function is generally preferred to facilitate hole injection into the organic layer. Examples include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

[0249] The above cathode material is preferably a material with a small work function to facilitate electron injection into an organic layer. Examples include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer materials such as LiF / Al or LiO2 / Al, but are not limited thereto.

[0250] The above-described light-emitting layer may include a host material and a dopant material. When an organic light-emitting device according to one embodiment of the present specification includes an additional light-emitting layer other than the light-emitting layer comprising Chemical Formula 1, the host material may include a condensed aromatic ring derivative or a heterocyclic compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compounds include dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but are not limited thereto.

[0251] The above dopant materials include aromatic amine derivatives, styramine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, aromatic amine derivatives are condensed aromatic ring derivatives having substituted or unsubstituted arylamine groups, such as pyrene, anthracene, chrysene, and periplantene having arylamine groups. In addition, styramine compounds are compounds in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, wherein one or more substituents selected from the group consisting of aryl groups, silyl groups, alkyl groups, cycloalkyl groups, and arylamine groups are substituted or unsubstituted. Specifically, styramine, styryldiamine, styryltriamine, styryltetraamine, etc. are examples, but are not limited thereto. In addition, metal complexes include iridium complexes, platinum complexes, etc., but are not limited thereto.

[0252] The hole injection layer described above is a layer that receives holes from an electrode. It is desirable for the hole injection material to have the ability to transport holes, thereby having an excellent hole injection effect for the hole receiving effect from the anode and for the light-emitting layer or light-emitting material. In addition, it is desirable for the material to have an excellent ability to prevent the movement of excitons generated in the light-emitting layer to the electron injection layer or electron injection material. In addition, it is desirable for the material to have an excellent thin film formation ability. Furthermore, it is desirable for the HOMO (highest occupied molecular orbital) of the hole injection material to be between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include, but are not limited to, metal porphyrins, oligothiophenes, arylamine-based organic materials; hexanitrile-hexaazatriphenylene-based organic materials; quinacridone-based organic materials; perylene-based organic materials; and polythiophene-based conductive polymers such as anthraquinone and polyaniline.

[0253] According to one embodiment of the present specification, the hole injection layer comprises a compound represented by the following chemical formula HI-1, but is not limited thereto.

[0254] [Chemical Formula HI-1]

[0255]

[0256] In the above chemical formula HI-1,

[0257] R315 to R317 are the same or different from one another and are each independently 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 are combined with adjacent groups to form a substituted or unsubstituted ring, and

[0258] r315 is an integer from 1 to 5, and if r315 is 2 or more, the 2 or more R315s are the same or different from each other,

[0259] r316 is an integer from 1 to 5, and if r316 is 2 or more, the 2 or more R316s are the same or different from each other.

[0260] According to one embodiment of the present specification, R317 is any one selected from the group consisting of a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and combinations thereof.

[0261] According to one embodiment of the present specification, the R317 is any one selected from the group consisting of a carbazole group; a phenyl group; a biphenyl group; a triphenylene group; and combinations thereof.

[0262] According to one embodiment of the present specification, R315 and R316 are the same or different from each other and are each independently substituted or unsubstituted aryl groups, or they combine with adjacent groups to form an aromatic hydrocarbon ring substituted with an alkyl group.

[0263] According to one embodiment of the present specification, R315 and R316 are the same or different from each other and each independently is a phenyl group or a biphenyl group, or combines with adjacent groups to form an indene substituted with a methyl group.

[0264] According to one embodiment of the present specification, the chemical formula HI-1 is represented by any one of the following compounds.

[0265]

[0266]

[0267] According to one embodiment of the present specification, the hole injection layer comprises a compound represented by the following chemical formula HI-2, but is not limited thereto.

[0268] [Chemical Formula HI-2]

[0269]

[0270] In the above chemical formula HI-2,

[0271] R401 to R403 are the same or the same as above, and each is independently a halogen group, and

[0272] r401 to r403 are 4.

[0273] According to one embodiment of the present specification, R401 to R403 are F.

[0274] According to one embodiment of the present specification, the chemical formula HI-2 is represented by the following compound.

[0275]

[0276] According to one embodiment of the present specification, the hole injection layer comprises the chemical formulas HI-1 and HI-2.

[0277] According to one embodiment of the present specification, the hole injection layer comprises the chemical formulas HI-1 and HI-2 in a weight ratio of 1:99 to 99:1.

[0278] The hole transport layer described above is a layer that receives holes from the hole injection layer and transports them to the emissive layer. As for the hole transport material, a material capable of receiving holes from the anode or the hole injection layer and transferring them to the emissive layer is preferably a material with high mobility for holes. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers containing both conjugated and non-conjugated portions.

[0279] According to one embodiment of the present specification, the hole transport layer comprises a compound represented by the chemical formula HI-1, but is not limited thereto.

[0280] According to one embodiment of the present specification, the hole injection and transport layer is a layer that transports holes to the light-emitting layer. Materials exemplified in the hole transport layer and hole injection layer may be used, but are not limited thereto.

[0281] The electron transport layer described above is a layer that receives electrons from the electron injection layer and transports them to the light-emitting layer. As for the electron transport material, a material capable of effectively receiving electrons from the cathode and transferring them to the light-emitting layer is preferred, and a material with high electron mobility is desirable. 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 in the prior art. In particular, a suitable cathode material is a conventional material having a low work function followed by an aluminum layer or a silver layer. Specifically, examples include cesium, barium, calcium, ytterbium, and samarium, each followed by an aluminum layer or a silver layer.

[0282] The electron injection layer is a layer that receives electrons from an electrode. It is desirable for the electron injection material to have excellent electron transport ability and to have an electron receiving effect from the second electrode, as well as an excellent electron injection effect on the emitting layer or emitting material. In addition, it is desirable for the material to prevent excitons generated in the emitting layer from moving to the hole injection layer and to have excellent thin film formation ability. Specifically, examples include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preolenylidene methane, anthrone, and their derivatives, metal complex compounds, and nitrogen-containing five-membered ring derivatives, but are not limited thereto.

[0283] 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 bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, but are not limited thereto.

[0284] 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 materials exemplified in the electron transport layer and electron injection layer may be used, but are not limited thereto.

[0285] According to one embodiment of the present specification, the electron injection and transport layer comprises a compound represented by the following chemical formula ET-1, but is not limited thereto.

[0286] [Chemical Formula ET-1]

[0287]

[0288] In the above chemical formula ET-1,

[0289] At least one of Z11 to Z13 is N, and the rest are CH, and

[0290] At least one of Z21 to Z23 is N, and the rest are CH, and

[0291] L601 and L602 are the same or different from each other, and each is independently a directly bonded; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, and

[0292] Ar601 to Ar604 are the same or different from one another and are each independently substituted or unsubstituted aryl groups; or substituted or unsubstituted heteroaryl groups.

[0293] According to one embodiment of the present specification, L601 and L602 are the same or different from each other and are each independently substituted or unsubstituted monocyclic or polycyclic arylene groups having 6 to 30 carbon atoms.

[0294] According to one embodiment of the present specification, L601 and L602 are phenylene groups.

[0295] According to one embodiment of the present specification, the Ar601 to Ar604 are the same or different from each other and are each independently substituted or unsubstituted monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms.

[0296] According to one embodiment of the present specification, Ar601 to Ar604 are phenyl groups.

[0297] According to one embodiment of the present specification, the chemical formula ET-1 is represented by the following compound.

[0298]

[0299] According to one embodiment of the present specification, the electron injection and transport layer may further comprise a metal complex compound. The metal complex compound is as described above.

[0300] The electron blocking layer described above is a layer capable of improving the lifespan and efficiency of the 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 may be used without limitation, and materials exemplified in the description of the hole injection layer may be used, but are not limited thereto. The electron blocking layer may be formed between the light-emitting layer and the hole transport layer, between the light-emitting layer and the hole injection layer, or between the light-emitting layer and a layer that performs both hole injection and hole transport simultaneously.

[0301] According to one embodiment of the present specification, the electron blocking layer comprises a compound represented by the following chemical formula EB-1, but is not limited thereto.

[0302] [Chemical Formula EB-1]

[0303]

[0304] In the above chemical formula EB-1,

[0305] T1 to T14 are the same or different from one another, and each independently hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0306] t13 is an integer from 1 to 3, and if t13 is 2 or more, the 2 or more t13s are the same or different from each other.

[0307] According to one embodiment of the present specification, T1 to T14 are the same or different from each other and are each independently hydrogen; deuterium; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0308] According to one embodiment of the present specification, T1 to T14 are the same or different from each other and are each independently hydrogen; deuterium; or a single or polycyclic aryl group having 6 to 20 carbon atoms.

[0309] According to one embodiment of the present specification, T1 to T14 are the same or different from each other and are each independently hydrogen; deuterium; phenyl group; biphenyl group; or naphthyl group.

[0310] According to one embodiment of the present specification, T1 to T13 are the same or different from each other and are each independently hydrogen; or deuterium.

[0311] According to one embodiment of the present specification, the T14 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0312] According to one embodiment of the present specification, the T14 is a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0313] According to one embodiment of the present specification, the T14 is a phenyl group; a biphenyl group; or a naphthyl group.

[0314] According to one embodiment of the present specification, the formula EB-1 may include the following compounds, but is not limited thereto.

[0315]

[0316] According to one embodiment of the present specification, the chemical formula EB-1 may be used as a second host material of the light-emitting layer.

[0317] The hole blocking layer described above is a layer that prevents holes from reaching the cathode and can generally be formed under the same conditions as the electron injection layer. In the case where an organic light-emitting device according to one embodiment of the present specification includes an additional hole blocking layer other than the hole blocking layer comprising Chemical Formula 1, specifically, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, aluminum complexes, etc., are included, but are not limited thereto.

[0318] The organic light-emitting device according to the present specification may be a front-emitting type, a back-emitting type, or a double-sided emitting type depending on the material used.

[0319] The organic light-emitting element according to the present specification may be included in and used in various electronic devices. For example, the electronic device may be a display panel, a touch panel, a solar module, a lighting device, etc., but is not limited thereto.

[0320] Hereinafter, in order to specifically explain the present specification, examples and comparative examples will be described in detail. However, the examples and comparative examples according to the present specification may be modified in various different forms, and the scope of the present specification is not to be interpreted as being limited to the examples and comparative examples described below. The examples and comparative examples of the present specification are provided to more completely explain the present specification to those with average knowledge in the art.

[0321] <Preparation Example 1> Synthesis of Compound 1

[0322]

[0323] Compound 9-(4-chloro-6-(4-(triphenylsilyl)phenyl)-1,3,5-triazin-2-yl)-9H-carbazole (5.50 g, 8.94 mmol) and a-1 (7.24, 15.28 mmol) were completely dissolved in 240 ml of tetrahydrofuran in a 500 ml round-bottom flask under a nitrogen atmosphere, followed by the addition of 2 M aqueous potassium carbonate solution (120 ml), tetrakis-(triphenylphosphine)palladium (0.48 g, 0.42 mmol), and heating and stirring for 5 hours. The temperature was lowered to room temperature, the water layer was removed, and the mixture was dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 310 ml of ethyl acetate to prepare Compound 1 (4.33 g, 53%).

[0324] MS[M+H] + = 912

[0325] <Preparation Example 2> Synthesis of Compound 2

[0326]

[0327] Compound 9-(4-chloro-6-(4-(triphenylsilyl)phenyl)-1,3,5-triazin-2-yl)-9H-carbazole (5.50 g, 8.94 mmol) and compound a-2 (7.24 g, 15.28 mmol) were completely dissolved in 240 mL of tetrahydrofuran in a 500 mL round-bottom flask under a nitrogen atmosphere, followed by the addition of 120 mL of 2 M aqueous potassium carbonate solution and tetrakis-(triphenylphosphine)palladium (0.48 g, 0.42 mmol), and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, and the mixture was dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 330 mL of ethyl acetate to prepare compound 2 (5.12 g, 63%).

[0328] MS[M+H] + = 912

[0329] <Preparation Example 3> Synthesis of Compound 3

[0330]

[0331] Compound 9-(4-chloro-6-(3-(triphenylsilyl)phenyl)-1,3,5-triazin-2-yl)-9H-carbazole (5.50 g, 8.94 mmol) and compound a-3 (7.24 g, 15.28 mmol) were completely dissolved in 240 mL of tetrahydrofuran in a 500 mL round-bottom flask under a nitrogen atmosphere, followed by the addition of 2 M aqueous potassium carbonate solution (120 mL), tetrakis-(triphenylphosphine)palladium (0.48 g, 0.42 mmol), and heating and stirring for 5 hours. The temperature was lowered to room temperature, the water layer was removed, and the mixture was dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 290 mL of ethyl acetate to prepare compound 3 (5.14 g, 63%).

[0332] MS[M+H] + = 912

[0333] <Preparation Example 4> Synthesis of Compound 4

[0334]

[0335] Compound 2-chloro-4-phenyl-6-(2-(triphenylsilyl)phenyl)-1,3,5-triazine (5.50 g, 8.94 mmol) and compound a-4 (7.24 g, 15.28 mmol) were completely dissolved in 240 mL of tetrahydrofuran in a 500 mL round-bottom flask under a nitrogen atmosphere, followed by the addition of 120 mL of 2 M aqueous potassium carbonate solution and tetrakis-(triphenylphosphine)palladium (0.48 g, 0.42 mmol), and the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the water layer was removed, and the mixture was dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 280 mL of ethyl acetate to prepare compound 4 (4.76 g, 58%).

[0336] MS[M+H] + = 766

[0337] <Preparation Example 5> Synthesis of Compound 5

[0338]

[0339] Compound 9-(4-chloro-6-(4-(triphenylsilyl)phenyl)-1,3,5-triazin-2-yl)-9H-carbazole (5.50 g, 8.94 mmol) and compound a-5 (7.24 g, 15.28 mmol) were completely dissolved in 240 mL of tetrahydrofuran in a 500 mL round-bottom flask under a nitrogen atmosphere, followed by the addition of 2 M aqueous potassium carbonate solution (120 mL), tetrakis-(triphenylphosphine)palladium (0.48 g, 0.42 mmol), and heating and stirring for 5 hours. The temperature was lowered to room temperature, the water layer was removed, and the mixture was dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 290 mL of ethyl acetate to prepare compound 5 (5.25 g, 64%).

[0340] MS[M+H] + = 912

[0341] <Preparation Example 6> Synthesis of Compound 6

[0342]

[0343] Compound 9-(4-chloro-6-(3-(triphenylsilyl)phenyl)-1,3,5-triazin-2-yl)-9H-carbazole (5.50 g, 8.94 mmol) and compound a-6 (7.24 g, 15.28 mmol) were completely dissolved in 240 mL of tetrahydrofuran in a 500 mL round-bottom flask under a nitrogen atmosphere, followed by the addition of 2 M aqueous potassium carbonate solution (120 mL), tetrakis-(triphenylphosphine)palladium (0.48 g, 0.42 mmol), and heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, and the mixture was dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 270 mL of ethyl acetate to prepare compound 6 (4.67 g, 578%).

[0344] MS[M+H] + = 912

[0345] <Preparation Example 7> Synthesis of Compound 7

[0346]

[0347] Compound 9-(4-chloro-6-(3-(triphenylsilyl)phenyl)-1,3,5-triazin-2-yl)-9H-carbazole (5.50 g, 8.94 mmol) and a-7 (7.24 g, 15.24 mmol) were completely dissolved in 240 ml of tetrahydrofuran in a 500 ml round-bottom flask under a nitrogen atmosphere, followed by the addition of 120 ml of 2 M aqueous potassium carbonate solution and tetrakis-(triphenylphosphine)palladium (0.48 g, 0.42 mmol), and the mixture was heated and stirred for 6 hours. The temperature was lowered to room temperature, the water layer was removed, and the mixture was dried with anhydrous magnesium sulfate. The mixture was then concentrated under reduced pressure and recrystallized with 270 ml of ethyl acetate to prepare compound 7 (4.28 g, 52%).

[0348] MS[M+H] + = 912

[0349] <Preparation Example 8> Synthesis of Compound 8

[0350]

[0351] Compound 9-(4-chloro-6-(3-(triphenylsilyl)phenyl)-1,3,5-triazin-2-yl)-9H-carbazole-1,2,3,4,5,6,7,8-d8 (5.50 g, 13.83 mmol) and a-2 (7.24 g, 15.28 mmol) were completely dissolved in 240 ml of tetrahydrofuran in a 500 ml round-bottom flask under a nitrogen atmosphere, followed by the addition of 120 ml of 2 M aqueous potassium carbonate solution and 0.48 g of tetrakis-(triphenylphosphine)palladium (0.42 mmol), and the mixture was heated and stirred for 8 hours. The temperature was lowered to room temperature, the water layer was removed, and the mixture was dried with anhydrous magnesium sulfate. The mixture was then concentrated under reduced pressure and recrystallized with 290 ml of ethyl acetate to prepare compound 8 (5.56 g, 68%).

[0352] MS[M+H] + = 920

[0353] <Preparation Example 9> Synthesis of Compound 9

[0354]

[0355] Compound 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-(3-(triphenylsilyl)phenyl)-1,3,5-triazine (5.50 g, 8.94 mmol) and compound a-8 (7.24 g, 15.28 mmol) were completely dissolved in 240 mL of tetrahydrofuran in a 500 mL round-bottom flask under a nitrogen atmosphere, followed by the addition of 2 M aqueous potassium carbonate solution (120 mL) and tetrakis-(triphenylphosphine)palladium (0.48 g, 0.42 mmol), and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, and the mixture was dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 260 mL of ethyl acetate to prepare compound 9 (5.88 g, 71%).

[0356] MS[M+H] + = 927

[0357] <Preparation Example 10> Synthesis of Compound 10

[0358]

[0359] Compound 9-(4-chloro-6-(3-(triphenylsilyl)phenyl)-1,3,5-triazin-2-yl)-9H-carbazole-1,2,3,4,5,6,7,8-d8 (5.50 g, 8.83 mmol) and compound a-9 (7.24 g, 15.28 mmol) were completely dissolved in 240 mL of tetrahydrofuran in a 500 mL round-bottom flask under a nitrogen atmosphere, followed by the addition of 2 M aqueous potassium carbonate solution (120 mL), tetrakis-(triphenylphosphine)palladium (0.48 g, 0.42 mmol), and heating and stirring for 5 hours. The temperature was lowered to room temperature, the water layer was removed, and the mixture was dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 290 mL of ethyl acetate to prepare compound 10 (5.52 g, 67%).

[0360] MS[M+H] + = 935

[0361] <Preparation Example 11> Synthesis of Compound 11

[0362]

[0363] Compound 9-(4-chloro-6-(4-(tris(phenyl-d5)silyl)phenyl-2,3,5,6-d4)-1,3,5-triazin-2-yl)-9H-carbazole-1,2,3,4,5,6,7,8-d8 (5.50 g, 8.55 mmol) and compound a-10 (7.24 g, 15.28 mmol) were completely dissolved in 240 mL of tetrahydrofuran in a 500 mL round-bottom flask under a nitrogen atmosphere, then 2 M aqueous potassium carbonate solution (120 mL) was added, tetrakis-(triphenylphosphine)palladium (0.48 g, 0.42 mmol) was added, and the mixture was heated and stirred for 3 hours. Compound 11 (4.77 g, 58%) was prepared by lowering the temperature to room temperature, removing the water layer, drying with anhydrous magnesium sulfate, concentrating under reduced pressure, and recrystallizing with 290 mL of ethyl acetate.

[0364] MS[M+H] + = 954

[0365] Example 1-1

[0366] A glass substrate coated with an 800 Å thin film of indium tin oxide (ITO) was placed in distilled water containing dissolved detergent and cleaned using ultrasound. Fischer Co. detergent was used, and distilled water that had been filtered twice using a Millerpore Co. filter was used. After cleaning the ITO for 30 minutes, the ultrasonic cleaning process was repeated twice with distilled water for 10 minutes. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned using isopropyl alcohol, acetone, and methanol as solvents, dried, and then transported to a plasma cleaner. Additionally, the substrate was cleaned using oxygen plasma for 5 minutes and then transported to a vacuum deposition machine.

[0367] A hole injection layer was formed on the prepared ITO transparent electrode, which is the anode, by thermal vacuum deposition of compounds HT1 and HI1 to a thickness of 100 Å in a ratio of 98:2 (molar ratio). A hole transport layer was formed by vacuum deposition of a compound (300 Å) represented by the chemical formula HT1 above the hole injection layer. Subsequently, an electron blocking layer was formed by vacuum deposition of a BH(p-type) compound to a film thickness of 50 Å on the hole transport layer. Subsequently, an emitting layer was formed on the electron blocking layer by vacuum deposition of a compound mixed in a 1:1 ratio of BH(p-type) and BH(n-type) represented by compound 1 synthesized in Preparation Example 1 as the host of the emitting layer, and a compound represented by the chemical formula BD below as the dopant of the emitting layer in a weight ratio of 88:12. A hole blocking layer was formed by vacuum depositing BH(n-type), represented by Compound 1 synthesized in Preparation Example 1, with a film thickness of 50 Å on the light-emitting layer. Subsequently, an electron injection and transport layer with a thickness of 300 Å was formed by vacuum depositing a compound represented by the chemical formula ET1 and a compound represented by the chemical formula LiQ in a weight ratio of 1:1 on the hole blocking layer. A cathode was formed by sequentially depositing lithium fluoride (LiF) with a thickness of 10 Å and aluminum with a thickness of 800 Å on the electron injection and transport layer.

[0368]

[0369] In the above process, the deposition rate of the organic material was maintained at 0.4–0.7 Å / sec, while the deposition rates for the cathode lithium fluoride and aluminum were maintained at 0.3 Å / sec and 2 Å / sec, respectively, and the vacuum level during deposition was 2 × 10⁻¹⁰ -7 ~ 5 x 10 -6 An organic light-emitting diode was fabricated by maintaining torr.

[0370] Examples 1-2 to 1-11

[0371] An organic light-emitting diode was prepared in the same manner as in Example 1-1, except that the compound listed in Table 1 below was used instead of the compound of Preparation Example 1.

[0372] Comparative Examples 1-1 to 1-6

[0373] An organic light-emitting diode was prepared in the same manner as in Example 1-1, except that the compounds listed in Table 1 below were used instead of the compounds of Preparation Example 1. The compounds of BH1 (n-type) to BH8 (n-type) used in Table 1 below are as follows.

[0374]

[0375] Experimental Example 1

[0376] When current was applied to the organic light-emitting diodes prepared in the above examples and comparative examples, the voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in Table 1 below.

[0377] In Table 1 below, T90 represents the time required for the luminance to decrease to 90% from the initial luminance (1600 nit), and the relative value is indicated based on Comparative Example 1-1.

[0378] Compound (Host) Voltage (V@10mA / cm²) 2 ) Efficiency (cd / A @ 10mA / cm²) 2 ) Color coordinates (x,y) T90 (relative value) Example 1-1 Compound 1 3.89 19.3 (0.136, 0.153) 1.38 Examples 1-2 Compound 2 3.84 19.2 (0.136, 0.154) 1.52 Examples 1-3 Compound 3 3.82 19.4 (0.136, 0.155) 1.47 Examples 1-4 Compound 4 3.86 19.5 (0.136, 0.153) 1.35 Examples 1-5 Compound 5 3.87 19.1 (0.136, 0.155) 1,32 Examples 1-6 Compound 6 3.88 19.7 (0.136, 0.154) 1.56 Examples 1-7 Compound 7 3.88 19.8 (0.136, 0.153) 1.48 Examples 1-8 Compound 8 3.89 19.9 (0.136, 0.155) 1.53 Examples 1-9 Compound 9 3.83 19.6 (0.136, 0.153) 1.77 Examples 1-10 Compound 10 3.83 19.3 (0.136, 0.154) 1.83 Example 1-11 Compound 11 3.82 19.5 (0.136, 0.154) 1.92 Comparative Example 1-1 BH1 4.03 16.9 (0.134, 0.162) 1 Comparative Example 1-2 BH2 4.14 18.1 (0.135, 0.163) 1.04 Comparative Examples 1-3 BH3 4.35 17.3 (0.134, 0.163) 0.78 Comparative Examples 1-4 BH4 4.26 17.1 (0.135, 0.163) 0.82 Comparative Examples 1-5 BH5 4.25 16.8 (0.135, 0.162) 1.09 Comparative Examples 1-6 BH6 4.13 18.4 (0.134, 0.161) 1.14 Comparative Examples 1-7 BH7 4.35 17.6 (0.135, 0.162) 0.91 Comparative Example 1-8 BH8 4.21 17.4 (0.135, 0.163) 0.86

[0379] As shown in Table 1 above, Examples 1-1 to 1-11, which are organic light-emitting devices using a compound of Formula 1 of the present specification (in which a triazine substituted with tetraphenylsilyl and carbazole groups is connected to a spiro[fluorene-9,9'-xanthene] core) as a host (BH(n-type)) of the organic light-emitting device, exhibited excellent characteristics in terms of efficiency, driving voltage, and stability of the organic light-emitting device.

[0380] Specifically, compared to Comparative Examples 1-1 and 1-5, which include only silyl groups in the triazine group; Comparative Examples 1-2 and 1-6, which include only carbazole groups in the triazine group; Comparative Examples 1-3 and 1-7, which include compounds in which carbazole is bonded to the triazine group as a C portion; and Comparative Examples 1-4 and 1-8, which include compounds in which a linker is included between the triazine group and the carbazole, Examples 1-1 to 1-11 of the present invention have excellent efficiency driving voltage and lifespan due to the following structural features.

[0381] The bulky silyl group of Chemical Formula 1 has a structural feature that stabilizes the excited and polaronic states of Chemical Formula 1 by participating in the conjugation system through a hyperconjugation effect. Additionally, by including a carbazole structure, the LUMO energy level of the compound can be increased, thereby preventing host-guest electrostatic coupling in the organic layer of an organic light-emitting device containing it. Therefore, Chemical Formula 1 can be incorporated into the organic layer of an organic light-emitting device to enable improved efficiency, lower driving voltage, and enhanced lifespan characteristics.

[0382] Although a preferred embodiment of the present invention (emissive layer BH n-type) has been described above, the present invention is not limited thereto and can be implemented with various modifications within the scope of the claims and the detailed description of the invention, and such modifications also fall within the scope of the invention. Explanation of the symbols

[0383] 1: Substrate 2: First electrode 3: Second electrode 4: Organic layer 5: Hole injection layer 6: Precision Transport Layer 7: Electromagnetic blocking layer 8: Emissive layer 9: Electron injection and transport layer

Claims

Claim 1 Compound of Chemical Formula 1 below: [Chemical Formula 1] In the above chemical formula 1, at least one of X1 to X3 is N and the remainder is CH; L1 and L2 are the same or different from each other and are each independently directly bonded; or are substituted or unsubstituted arylene groups; R1 to R3 are the same or different from each other and are each independently substituted or unsubstituted alkyl groups; or are substituted or unsubstituted aryl groups; and G1 to G5 are the same or different from each other and are each independently hydrogen; deuterium; or a substituted or unsubstituted aryl group, g1 to g4 are each integers from 0 to 4, g5 is an integer from 0 to 8, where g1 is 2 or more, the 2 or more G1s are the same or different from each other, where g2 is 2 or more, the 2 or more G2s are the same or different from each other, where g3 is 2 or more, the 2 or more G3s are the same or different from each other, where g4 is 2 or more, the 2 or more G4s are the same or different from each other, where g5 is 2 or more, the 2 or more G5s are the same or different from each other, and 0 ≤ g1 + g2 ≤ 7. Claim 2 A compound according to claim 1, wherein Chemical Formula 1 is any one of the following Chemical Formulas 1-1 to 1-4: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] In the above chemical formulas 1-1 to 1-4, the definitions of X1 to X3, L1, L2, R1 to R3, G1 to G5, and g2 to g5 are the same as those defined in the above chemical formula 1, g'1 is an integer from 0 to 3, and when g'1 is 2 or more, the 2 or more G1s are the same or different from each other. Claim 3 A compound according to claim 1, wherein Chemical Formula 1 is any one of the following Chemical Formulas 1-5 to 1-8: [Chemical Formula 1-5] [Chemical Formula 1-6] [Chemical Formula 1-7] [Chemical Formula 1-8] In the above chemical formulas 1-5 to 1-8, the definitions of X1 to X3, L1, L2, R1 to R3, G1 to G5, g1, and g3 to g5 are the same as those defined in the above chemical formula 1, and g'2 is an integer from 0 to 3, and when g'2 is 2 or more, the 2 or more G2s are the same or different from each other. Claim 4 A compound according to claim 1, wherein Chemical Formula 1 is any one of the following Chemical Formulas 2 to 6: [Chemical Formula 2] [Chemical Formula 3] [Chemical Formula 4] [Chemical Formula 5] [Chemical Formula 6] In the above chemical formulas 2 to 6, the definitions of L1, L2, R1 to R3, G1 to G5, and g1 to g5 are the same as those defined in the above chemical formula 1. Claim 5 A compound according to claim 1, wherein X1 to X3 are N, L1 is a direct bond, L2 is a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium, R1 to R3 are the same or different from each other and are each independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium, G1 to G4 are the same or different from each other and are each independently hydrogen; or deuterium, and G5 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with hydrogen; deuterium; or deuterium. Claim 6 A compound according to claim 1, wherein the chemical formula 1 is any one of the following compounds: In the above compound, D is deuterium, and n is an integer from 0 to 42. Claim 7 An organic light-emitting device comprising: a first electrode; a second electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers comprise a compound of any one of claims 1 to 6. Claim 8 An organic light-emitting device according to claim 7, wherein the organic layer comprises an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer comprises the compound. Claim 9 An organic light-emitting device according to claim 7, wherein the organic layer comprises a hole-blocking layer, and the hole-blocking layer comprises the compound. Claim 10 An organic light-emitting device according to claim 7, wherein the organic layer comprises a light-emitting layer, and the light-emitting layer comprises the compound. Claim 11 An organic light-emitting device according to claim 7, wherein the organic layer comprises a light-emitting layer, and the light-emitting layer comprises the compound as a host of the light-emitting layer.

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