Heterocyclic compound and organic light-emitting device comprising same

Abstract

The present specification relates to a heterocyclic compound represented by chemical formula 1, and an organic light-emitting device comprising same. The definitions of substituents in chemical formula 1 are the same as those disclosed in the description.

Description

Heterocyclic compound and organic light-emitting device containing the same

[0001] This application claims the benefit of priority from Republic of Korea Patent Application No. 10-2023-0092666, dated July 17, 2023, and all contents of that Republic of Korea patent application are incorporated herein by reference.

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

[0003] Organic light-emitting diodes are a type of self-luminous display device that have the advantages of a wide viewing angle, excellent contrast, and fast response speed.

[0004] Organic light-emitting devices have a structure in which an organic thin film is placed between two electrodes. When voltage is applied to an organic light-emitting device of this structure, electrons and holes injected from the two electrodes combine in the organic thin film, forming pairs and then disappearing, emitting light. The organic thin film may be composed of a single layer or multiple layers, as needed.

[0005] The material of the organic thin film may have a light-emitting function as needed. For example, the organic thin film material may be a compound that can form a light-emitting layer on its own, or a compound that can act as a host or dopant in a host-dopant light-emitting layer. In addition, the material of the organic thin film may be a compound that can perform roles such as hole injection, hole transport, electron blocking, hole blocking, electron transport, and electron injection.

[0006] To improve the performance, lifespan, or efficiency of organic light-emitting devices, the development of materials for organic thin films is continuously required.

[0007] [Prior Art Literature]

[0008] [Patent Document]

[0009] (Patent Document 1) U.S. Patent No. 4,356,429

[0010] The present specification provides a heterocyclic compound and an organic light-emitting device including the same.

[0011] In one embodiment of the present application, a heterocyclic compound represented by the following chemical formula 1 is provided.

[0012] [Chemical Formula 1]

[0013]

[0014] In the above chemical formula 1,

[0015] A1 to A5 are the same as or different from each other, and each independently represent hydrogen; deuterium; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R101R102; -SiR101R102R103 and a group represented by the following chemical formula 2, or two or more adjacent groups are combined to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same as or different from each other, and each independently represent a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0016] At least one of the above A1 to A5 is a group represented by the following chemical formula 2,

[0017] [Chemical Formula 2]

[0018]

[0019] B1 to B4 are the same as or different from each other, and each independently represent hydrogen; deuterium; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R101R102 and -SiR101R102R103, or two or more adjacent groups are combined to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same or different from each other and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0020] At least two of the above B1 to B4 are substituted or unsubstituted C1 to C60 alkyl groups,

[0021] In the above chemical formula 2,

[0022] L1 to L3 are the same or different and each independently represents a single bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group,

[0023] Ar1 and Ar2 are the same or different, and each independently represents a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0024] n1 to n3 are equal to or different from each other and are each independently an integer from 0 to 3,

[0025] If n1 is 2 or greater, L1 is equal or different,

[0026] If n2 is 2 or greater, L2 is equal or different,

[0027] If n3 is 2 or greater, L3 is equal or different,

[0028] n4 and n5 are equal to or different from each other and are each independently an integer from 1 to 5,

[0029] If n4 is 2 or greater, Ar1 is equal or different,

[0030] If n5 is 2 or greater, Ar2 is equal or different.

[0031] In addition, in one embodiment of the present application, an organic light-emitting device is provided, including a first electrode; a second electrode provided opposite the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein the organic layers include one or more types of the heterocyclic compounds.

[0032] The heterocyclic compound according to one embodiment can be used as an organic layer material of an organic light-emitting device. The heterocyclic compound can perform the roles of a hole injection material, a hole transport material, a light-emitting material, an electron transport material, an electron injection material, etc. in the organic light-emitting device. In particular, the heterocyclic compound can be used as a hole transport layer or a hole transport auxiliary layer material of the organic light-emitting device.

[0033] Therefore, when the compound represented by the above chemical formula 1 is used in the organic layer, the driving voltage of the organic light-emitting device can be lowered, the luminous efficiency can be improved, and the lifespan characteristics of the organic light-emitting device can be improved due to the thermal stability of the compound.

[0034] Figures 1 to 3 are drawings schematically showing the laminated structure of an organic light-emitting device according to one embodiment of the present invention.

[0035] Hereinafter, the present invention will be described in more detail.

[0036] In this specification, the term "substitution" 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 a hydrogen atom is replaced, i.e., a position where a 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.

[0037] In this specification, "substituted or unsubstituted" means: deuterium; cyano group; straight or branched chain alkyl group having 1 to 60 carbon atoms; straight or branched chain alkenyl group having 2 to 60 carbon atoms; straight or branched chain alkynyl group having 2 to 60 carbon atoms; monocyclic or polycyclic cycloalkyl group having 3 to 60 carbon atoms; monocyclic or polycyclic heterocycloalkyl group having 2 to 60 carbon atoms; monocyclic or polycyclic aryl group having 6 to 60 carbon atoms; monocyclic or polycyclic heteroaryl group having 2 to 60 carbon atoms; -SiRR'R"; -P(=O)RR'; C1 to C20 alkylamine group; C6 to C60 monocyclic or polycyclic arylamine group; and C2 to C60 monocyclic or polycyclic heteroarylamine group, which is substituted or unsubstituted with one or more substituents selected from the group consisting of a C1 to C20 alkylamine group; a C6 to C60 monocyclic or polycyclic arylamine group; and a C2 to C60 monocyclic or polycyclic heteroarylamine group, or substituted or unsubstituted with a substituent in which two or more substituents selected from the above-mentioned substituents are connected.

[0038] In this specification, “proton number” means the number of substituents that a specific compound can have, and specifically, the proton number can mean the number of hydrogens.

[0039] For example, unsubstituted benzene can be represented by the number of protons being 5, unsubstituted naphthyl groups can be represented by the number of protons being 7, naphthyl groups substituted with phenyl groups can be represented by the number of protons being 6, and unsubstituted biphenyl groups can be represented by the number of protons being 9.

[0040] In the present specification, an alkyl group includes a straight or branched chain having 1 to 60 carbon atoms, and may be further substituted by another substituent. The alkyl group may have 1 to 60 carbon atoms, specifically 1 to 40 carbon atoms, and more specifically 1 to 20 carbon atoms. 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.

[0041] In the present specification, the alkenyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted by another substituent. The alkenyl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 2 to 20 carbon atoms. 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.

[0042] In the present specification, an alkynyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted by another substituent. The alkynyl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 2 to 20 carbon atoms.

[0043] In the present specification, the alkoxy group may be linear, branched or cyclic. The carbon number of the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms. Specifically, examples thereof include, but are not limited to, 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, and a p-methylbenzyloxy group.

[0044] In the present specification, a cycloalkyl group includes a monocyclic or polycyclic group having 3 to 60 carbon atoms, and may be further substituted by another substituent. Here, polycyclic means a group in which a cycloalkyl group is directly connected to or condensed with another ring group. Here, the other ring group may be a cycloalkyl group, but may also be another type of ring group, such as a heterocycloalkyl group, an aryl group, a heteroaryl group, etc. The cycloalkyl group may have 3 to 60 carbon atoms, specifically 3 to 40 carbon atoms, and more specifically 5 to 20 carbon atoms. Specifically, there are, but are 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, etc.

[0045] In the present specification, a heterocycloalkyl group includes O, S, Se, N or Si as a heteroatom, and includes a monocyclic or polycyclic group having 2 to 60 carbon atoms, and may be further substituted by another substituent. Here, polycyclic means a group in which a heterocycloalkyl group is directly connected to or condensed with another ring group. Here, the other ring group may be a heterocycloalkyl group, but may also be another type of ring group, such as a cycloalkyl group, an aryl group, a heteroaryl group, etc. The heterocycloalkyl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 3 to 20 carbon atoms.

[0046] In the present specification, an aryl group includes a monocyclic or polycyclic ring having 6 to 60 carbon atoms, and may be further substituted by another substituent. Here, polycyclic means a group in which an aryl group is directly connected to or condensed with another ring group. Here, the other ring group may be an aryl group, but may also be another type of ring group, such as a cycloalkyl group, a heterocycloalkyl group, a heteroaryl group, etc. The aryl group may include a spiro group. The aryl group may have 6 to 60 carbon atoms, specifically 6 to 40 carbon atoms, and more specifically 6 to 25 carbon atoms. Specific examples of the above aryl group include, but are not limited to, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a chrysenyl group, a phenanthrenyl group, a perylenyl group, a fluoranthenyl group, a triphenylenyl group, a phenalenyl group, a pyrenyl group, a tetracenyl group, a pentacenyl group, a fluorenyl group, an indenyl group, an acenaphthylenyl group, a benzofluorenyl group, a spirobifluorenyl group, a 2,3-dihydro-1H-indenyl group, and condensed ring groups thereof.

[0047] In the present specification, the phosphine oxide group is represented by -P(=O)R101R102, where R101 and R102 are the same or different, and each independently may be a substituent composed of at least one of hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; an aryl group; and a heterocyclic group. Specifically, it may be substituted with an aryl group, and the above-described examples may be applied to the aryl group. For example, the phosphine oxide group includes, but is not limited to, a diphenylphosphine oxide group, dinaphthylphosphine oxide, etc.

[0048] In the present specification, a silyl group is a substituent that contains Si and is directly connected to the Si atom as a radical, and is represented by -SiR101R102R103, wherein R101 to R103 are the same as or different from each other, and may each independently be a substituent composed of at least one of hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; an aryl group; and a heterocyclic group. Specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.

[0049] In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be combined with each other to form a ring.

[0050] When the above fluorenyl group is substituted, the structural formula below may be used, but is not limited thereto.

[0051]

[0052] In the present specification, a spiro group is a group including a spiro structure and may have 15 to 60 carbon atoms. For example, the spiro group may include a structure in which a 2,3-dihydro-1H-indene group or a cyclohexane group is spiro-bonded to a fluorenyl group. Specifically, the following spiro group may include any one of the groups having the following structural formula.

[0053]

[0054] In the present specification, a heteroaryl group includes S, O, Se, N or Si as a heteroatom, and includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted by another substituent. Here, the polycyclic ring means a group in which a heteroaryl group is directly connected to or condensed with another ring group. Here, the other ring group may be a heteroaryl group, but may also be another type of ring group, such as a cycloalkyl group, a heterocycloalkyl group, an aryl group, etc. The heteroaryl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 3 to 25 carbon atoms.Specific examples of the above heteroaryl group include a pyridyl group, a pyrrolyl group, a pyrimidyl group, a pyridazinyl group, a furanyl group, a thiophenyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, a furazanyl group, an oxadiazolyl group, a thiadiazolyl group, a dithiazolyl group, a tetrazolyl group, a pyranyl group, a thiopyranyl group, a diazinyl group, an oxazinyl group, a thiazinyl group, a deoxynyl group, a triazinyl group, a tetrazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, an isoquinazolinyl group, a quinozolinyl group, a naphthyridyl group, an acridinyl group, a phenanthridinyl group, an imidazopyridinyl group, a diazanaphthalenyl group, Triazaindenyl group, 2-indolyl group, indolizinyl group, benzothiazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiophenyl group, benzofuranyl group, dibenzothiophenyl group, dibenzofuranyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, phenazinyl group, dibenzosilole group, spirobi(dibenzosilole) group, dihydrophenazinyl group, phenoxazinyl group, phenanthridyl group, thienyl group, indolo[2,3-a]carbazolyl group, indolo[2,3-b]carbazolyl group, indolinyl group, 10,11-dihydro-dibenzo[b,f]azepinyl group, 9,10-dihydroacridinyl group, phenanthrazinyl group, phenothiazinyl group, Examples thereof include, but are not limited to, a phthalazinyl group, a naphthyridinyl group, a phenanthrolinyl group, a benzo[c][1,2,5]thiadiazolyl group, a 5,10-dihydrodibenzo[b,e][1,4]azacylinyl group, a pyrazolo[1,5-c]quinazolinyl group, a pyrido[1,2-b]indazolyl group, a pyrido[1,2-a]imidazo[1,2-e]indolinyl group, and a 5,11-dihydroindeno[1,2-b]carbazolyl group.

[0055] In the present specification, the amine group may be selected from the group consisting of a monoalkylamine group; a monoarylamine group; a monoheteroarylamine group; -NH2; a dialkylamine group; a diarylamine group; a diheteroarylamine group; an alkylarylamine group; an alkylheteroarylamine group; and an arylheteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the above amine group include, but are not limited to, a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, a dibiphenylamine group, anthracenylamine group, a 9-methyl-anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a triphenylamine group, a biphenylnaphthylamine group, a phenylbiphenylamine group, a biphenylfluorenylamine group, a phenyltriphenylenylamine group, and a biphenyltriphenylenylamine group.

[0056] In this specification, an arylene group means a group having two bonding positions to an aryl group, i.e., a divalent group. The description of the aryl group described above may be applied to these groups, except that each group is divalent. In addition, a heteroarylene group means a group having two bonding positions to a heteroaryl group, i.e., a divalent group. The description of the heteroaryl group described above may be applied to these groups, except that each group is divalent.

[0057] As used herein, the term "adjacent" may refer to a substituent substituted on an atom directly connected to the atom substituted by the substituent, a substituent sterically closest to the substituent, or another substituent substituted on the atom substituted by the substituent. For example, two substituents substituted at ortho positions on a benzene ring and two substituents substituted on the same carbon in an aliphatic ring may be interpreted as "adjacent" to each other.

[0058] In the present invention, "when no substituent is indicated in the chemical formula or compound structure" means that a hydrogen atom is bonded to a carbon atom. However, deuterium ( 2H, Deuterium) is an isotope of hydrogen, so some hydrogen atoms may be deuterium.

[0059] In one embodiment of the present invention, “when no substituent is indicated in the chemical formula or compound structure” may mean that all positions that can be substituted are hydrogen or deuterium. That is, in the case of deuterium, it is an isotope of hydrogen, and some hydrogen atoms may be the isotope deuterium, and in this case, the deuterium content may be 0% to 100%.

[0060] In one embodiment of the present invention, in cases where “no substituent is indicated in the chemical formula or compound structure,” hydrogen and deuterium may be used in combination in the compound, unless deuterium is explicitly excluded, such as “the content of deuterium is 0%,” “the content of hydrogen is 100%,” or “all substituents are hydrogen.”

[0061] In one embodiment of the present invention, deuterium is an element having a deuteron, which is one of the isotopes of hydrogen and is composed of one proton and one neutron, as its nucleus, and can be expressed as hydrogen-2, and its element symbol is D or 2 It can also be written as H.

[0062] In one embodiment of the present invention, an isotope means an atom having the same atomic number (Z) but a different mass number (A), and an isotope can also be interpreted as an element having the same number of protons but a different number of neutrons.

[0063] In one embodiment of the present invention, the content T% of a specific substituent can be defined as T2 / T1×100 = T% when the total number of substituents that the basic compound can have is defined as T1, and the number of specific substituents among them is defined as T2.

[0064] That is, in one example, In the phenyl group represented by , the content of deuterium of 20% can mean that the total number of substituents that the phenyl group can have is 5 (T1 in the formula), and among them, the number of deuterium is 1 (T2 in the formula). That is, the content of deuterium of 20% in the phenyl group can be expressed by the structural formula below.

[0065]

[0066] Additionally, in one embodiment of the present invention, “a phenyl group having a deuterium content of 0%” may mean a phenyl group that does not contain a deuterium atom, i.e., has 5 hydrogen atoms.

[0067] In the present invention, the C6 to C60 aromatic hydrocarbon ring means a compound including an aromatic ring composed of C6 to C60 carbons and hydrogen, and examples thereof include, but are not limited to, benzene, biphenyl, terphenyl, triphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, azulene, etc., and includes all aromatic hydrocarbon ring compounds known in the art that satisfy the above carbon number.

[0068] In one embodiment of the present application, a heterocyclic compound represented by the following chemical formula 1 is provided.

[0069] [Chemical Formula 1]

[0070]

[0071] In the above chemical formula 1,

[0072] A1 to A5 are the same as or different from each other, and each independently represent hydrogen; deuterium; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R101R102; -SiR101R102R103 and a group represented by the following chemical formula 2, or two or more adjacent groups are combined to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same as or different from each other, and each independently represent a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0073] At least one of the above A1 to A5 is a group represented by the following chemical formula 2,

[0074] [Chemical Formula 2]

[0075]

[0076] B1 to B4 are the same as or different from each other, and each independently represent hydrogen; deuterium; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R101R102 and -SiR101R102R103, or two or more adjacent groups are combined to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same or different from each other and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0077] At least two of the above B1 to B4 are substituted or unsubstituted C1 to C60 alkyl groups,

[0078] In the above chemical formula 2,

[0079] L1 to L3 are the same or different and each independently represents a single bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group,

[0080] Ar1 and Ar2 are the same or different, and each independently represents a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0081] n1 to n3 are equal to or different from each other and are each independently an integer from 0 to 3,

[0082] If n1 is 2 or greater, L1 is equal or different,

[0083] If n2 is 2 or greater, L2 is equal or different,

[0084] If n3 is 2 or greater, L3 is equal or different,

[0085] n4 and n5 are equal to or different from each other and are each independently an integer from 1 to 5,

[0086] If n4 is 2 or greater, Ar1 is equal or different,

[0087] If n5 is 2 or greater, Ar2 is equal or different.

[0088] In one embodiment of the present application, A1 to A5 in Chemical Formula 1 are the same as or different from each other, and each independently represent hydrogen; deuterium; a cyano group; a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C2 to C40 alkenyl group; a substituted or unsubstituted C2 to C40 alkynyl group; a substituted or unsubstituted C1 to C40 alkoxy group; a substituted or unsubstituted C3 to C40 cycloalkyl group; a substituted or unsubstituted C2 to C40 heterocycloalkyl group; a substituted or unsubstituted C6 to C40 aryl group; a substituted or unsubstituted C2 to C40 heteroaryl group; -P(=O)R101R102; -SiR101R102R103 and a group represented by the above chemical formula 2, or two or more adjacent groups are combined to form a substituted or unsubstituted C6 to C40 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C40 heterocycle, wherein R101, R102 and R103 are the same as or different from each other, and each independently represent a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group, wherein at least one of A1 to A5 may be a group represented by the above chemical formula 2.

[0089] In one embodiment of the present application, A1 to A5 in Chemical Formula 1 are the same as or different from each other, and each independently represent hydrogen; deuterium; a cyano group; a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C2 to C30 alkenyl group; a substituted or unsubstituted C2 to C30 alkynyl group; a substituted or unsubstituted C1 to C30 alkoxy group; a substituted or unsubstituted C3 to C30 cycloalkyl group; a substituted or unsubstituted C2 to C30 heterocycloalkyl group; a substituted or unsubstituted C6 to C30 aryl group; a substituted or unsubstituted C2 to C30 heteroaryl group; -P(=O)R101R102; -SiR101R102R103 and a group represented by the above chemical formula 2, or two or more adjacent groups are combined to form a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C30 heterocycle, wherein R101, R102 and R103 are the same as or different from each other, and each independently represent a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group, wherein at least one of A1 to A5 may be a group represented by the above chemical formula 2.

[0090] In one embodiment of the present application, A1 to A5 in Chemical Formula 1 are the same as or different from each other, and each independently represent hydrogen; deuterium; a cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C2 to C20 alkenyl group; a substituted or unsubstituted C2 to C20 alkynyl group; a substituted or unsubstituted C1 to C20 alkoxy group; a substituted or unsubstituted C3 to C20 cycloalkyl group; a substituted or unsubstituted C2 to C20 heterocycloalkyl group; a substituted or unsubstituted C6 to C20 aryl group; a substituted or unsubstituted C2 to C20 heteroaryl group; A group consisting of groups represented by the above chemical formula 2, or two or more adjacent groups bonded to each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C20 heterocycle, wherein at least one of the above A1 to A5 may be a group represented by the above chemical formula 2.

[0091] In one embodiment of the present application, A1 to A5 of Chemical Formula 1 are the same as or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C6 to C20 aryl group; or a group represented by Chemical Formula 2, wherein at least one of A1 to A5 may be a group represented by Chemical Formula 2.

[0092] In one embodiment of the present application, A1 to A5 of Chemical Formula 1 are the same as or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted triphenylenyl group; or a substituted or unsubstituted dimethylfluorenyl group; or a group represented by Chemical Formula 2, wherein at least one of A1 to A5 may be a group represented by Chemical Formula 2.

[0093] In one embodiment of the present application, A1 of chemical formula 1 is a group represented by chemical formula 2, A2 to A4 are the same as or different from each other, and are each independently hydrogen or deuterium, and A5 may be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted triphenylenyl group; or a substituted or unsubstituted dimethylfluorenyl group.

[0094] In one embodiment of the present application, A2 of Chemical Formula 1 is a group represented by Chemical Formula 2, A1, A3 and A4 are the same as or different from each other, and are each independently hydrogen or deuterium, and A5 may be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted triphenylenyl group; or a substituted or unsubstituted dimethylfluorenyl group.

[0095] In one embodiment of the present application, A3 of chemical formula 1 is a group represented by chemical formula 2, A1, A2 and A4 are the same as or different from each other, and are each independently hydrogen or deuterium, and A5 may be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted triphenylenyl group; or a substituted or unsubstituted dimethylfluorenyl group.

[0096] In one embodiment of the present application, A4 of Chemical Formula 1 is a group represented by Chemical Formula 2, A1 to A3 are the same as or different from each other, and are each independently hydrogen or deuterium, and A5 may be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted triphenylenyl group; or a substituted or unsubstituted dimethylfluorenyl group.

[0097] In one embodiment of the present application, A5 of chemical formula 1 is a group represented by chemical formula 2, and A1 to A4 are the same as or different from each other, and may each independently be hydrogen or deuterium.

[0098] In one embodiment of the present application, B1 to B4 in Chemical Formula 1 are the same as or different from each other, and each independently represent hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C2 to C40 alkenyl group; a substituted or unsubstituted C2 to C40 alkynyl group; a substituted or unsubstituted C1 to C40 alkoxy group; a substituted or unsubstituted C3 to C40 cycloalkyl group; a substituted or unsubstituted C2 to C40 heterocycloalkyl group; a substituted or unsubstituted C6 to C40 aryl group; a substituted or unsubstituted C2 to C40 heteroaryl group; -P(=O)R101R102 and -SiR101R102R103, or two or more adjacent groups are combined to form a substituted or unsubstituted C6 to C40 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C40 heterocycle, wherein R101, R102 and R103 are the same or different, and each independently represent a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group, wherein at least two of B1 to B4 may be substituted or unsubstituted C1 to C40 alkyl groups.

[0099] In one embodiment of the present application, B1 to B4 in Chemical Formula 1 are the same as or different from each other, and each independently represent hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C2 to C30 alkenyl group; a substituted or unsubstituted C2 to C30 alkynyl group; a substituted or unsubstituted C1 to C30 alkoxy group; a substituted or unsubstituted C3 to C30 cycloalkyl group; a substituted or unsubstituted C2 to C30 heterocycloalkyl group; a substituted or unsubstituted C6 to C30 aryl group; a substituted or unsubstituted C2 to C30 heteroaryl group; -P(=O)R101R102 and -SiR101R102R103, or two or more adjacent groups are combined to form a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C30 heterocycle, wherein R101, R102 and R103 are the same as or different from each other, and each independently represent a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group, wherein at least two of B1 to B4 may be substituted or unsubstituted C1 to C30 alkyl groups.

[0100] In one embodiment of the present application, B1 to B4 in Chemical Formula 1 are the same as or different from each other, and each independently represent hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C2 to C20 alkenyl group; a substituted or unsubstituted C2 to C20 alkynyl group; a substituted or unsubstituted C1 to C20 alkoxy group; a substituted or unsubstituted C3 to C20 cycloalkyl group; a substituted or unsubstituted C2 to C20 heterocycloalkyl group; a substituted or unsubstituted C6 to C20 aryl group; And is selected from the group consisting of a substituted or unsubstituted C2 to C20 heteroaryl group, or two or more adjacent groups are combined with each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C20 heterocycle, and at least two of the B1 to B4 may be a substituted or unsubstituted C1 to C20 alkyl group.

[0101] In one embodiment of the present application, B1 to B4 in chemical formula 1 are the same as or different from each other, and are each independently hydrogen; deuterium; or a substituted or unsubstituted C1 to C10 alkyl group, and at least two of B1 to B4 may be substituted or unsubstituted C1 to C10 alkyl groups.

[0102] In one embodiment of the present application, B1 to B4 in chemical formula 1 are the same as or different from each other, and are each independently hydrogen; deuterium; or a substituted or unsubstituted C3 to C10 alkyl group, and at least two of B1 to B4 may be substituted or unsubstituted C3 to C10 alkyl groups.

[0103] In one embodiment of the present application, B1 to B4 in chemical formula 1 may be the same as or different from each other, and may each independently be hydrogen; deuterium; a substituted or unsubstituted isopropyl group; or a substituted or unsubstituted tert-butyl group, and at least two of B1 to B4 may be a substituted or unsubstituted isopropyl group; or a substituted or unsubstituted tert-butyl group.

[0104] In one embodiment of the present application, B1 and B2 in chemical formula 1 may be the same as or different from each other, and may each independently be a substituted or unsubstituted isopropyl group; or a substituted or unsubstituted tert-butyl group, and B3 and B4 may be the same as or different from each other, and may each independently be hydrogen; or deuterium.

[0105] In one embodiment of the present application, B1 and B3 in chemical formula 1 may be the same as or different from each other, and may each independently be a substituted or unsubstituted isopropyl group; or a substituted or unsubstituted tert-butyl group, and B2 and B4 may be the same as or different from each other, and may each independently be hydrogen; or deuterium.

[0106] In one embodiment of the present application, B1 and B4 in chemical formula 1 may be the same as or different from each other, and may each independently be a substituted or unsubstituted isopropyl group; or a substituted or unsubstituted tert-butyl group, and B2 and B3 may be the same as or different from each other, and may each independently be hydrogen; or deuterium.

[0107] In one embodiment of the present application, B2 and B3 in chemical formula 1 may be the same as or different from each other, and may each independently be a substituted or unsubstituted isopropyl group; or a substituted or unsubstituted tert-butyl group, and B1 and B4 may be the same as or different from each other, and may each independently be hydrogen; or deuterium.

[0108] In one embodiment of the present application, B2 and B4 in chemical formula 1 may be the same as or different from each other, and may each independently be a substituted or unsubstituted isopropyl group; or a substituted or unsubstituted tert-butyl group, and B1 and B3 may be the same as or different from each other, and may each independently be hydrogen; or deuterium.

[0109] In one embodiment of the present application, B3 and B4 in chemical formula 1 may be the same as or different from each other, and may each independently be a substituted or unsubstituted isopropyl group; or a substituted or unsubstituted tert-butyl group, and B1 and B2 may be the same as or different from each other, and may each independently be hydrogen; or deuterium.

[0110] In one embodiment of the present application, L1 to L3 of chemical formula 2 may be the same as or different from each other, and may each independently be a single bond; a substituted or unsubstituted C6 to C40 arylene group; or a substituted or unsubstituted C2 to C40 heteroarylene group.

[0111] In one embodiment of the present application, L1 to L3 in chemical formula 2 may be the same as or different from each other, and may each independently be a single bond; a substituted or unsubstituted C6 to C30 arylene group; or a substituted or unsubstituted C2 to C30 heteroarylene group.

[0112] In one embodiment of the present application, L1 to L3 of chemical formula 2 may be the same as or different from each other, and may each independently be a single bond; or a substituted or unsubstituted C6 to C20 arylene group.

[0113] In one embodiment of the present application, L1 to L3 in chemical formula 2 may be the same as or different from each other, and may each independently be a single bond; a substituted or unsubstituted C6 to C10 arylene group; or a substituted or unsubstituted C2 to C10 heteroarylene group.

[0114] In one embodiment of the present application, L1 to L3 of chemical formula 2 may be the same as or different from each other, and may each independently be a single bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted terphenylene group; or a substituted or unsubstituted naphthylene group.

[0115] In one embodiment of the present application, Ar1 and Ar2 in chemical formula 2 may be the same as or different from each other, and may each independently be a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0116] In one embodiment of the present application, Ar1 and Ar2 in chemical formula 2 may be the same as or different from each other, and may each independently be a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0117] In one embodiment of the present application, Ar1 and Ar2 in chemical formula 2 may be the same as or different from each other, and may each independently be a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0118] In one embodiment of the present application, Ar1 and Ar2 in chemical formula 2 may be the same as or different from each other, and may each independently be a substituted or unsubstituted C6 to C10 aryl group; or a substituted or unsubstituted C2 to C10 heteroaryl group.

[0119] In one embodiment of the present application, Ar1 and Ar2 of chemical formula 2 may be the same as or different from each other, and may each independently be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted triphenylenyl group; a substituted or unsubstituted dimethylfluorenyl group; a substituted or unsubstituted diphenylfluorenyl group; a substituted or unsubstituted spirobifluorenyl group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group.

[0120] In one embodiment of the present application, the chemical formula 1 may be represented by either the following chemical formula 1-1 or chemical formula 1-2.

[0121] [Chemical Formula 1-1]

[0122]

[0123] [Chemical Formula 1-2]

[0124]

[0125] In the above chemical formula 1-1,

[0126] A1 to A4 are the same as or different from each other, and each independently represent hydrogen; deuterium; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R101R102; -SiR101R102R103 and a group represented by the above chemical formula 2, or two or more adjacent groups are combined to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same as or different from each other and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0127] At least one of the above A1 to A4 is a group represented by the above chemical formula 2,

[0128] L4 is a single bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group,

[0129] Ar3 is a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0130] n6 is an integer from 0 to 3, and if it is 2 or greater, L4 is equal or different,

[0131] n7 is an integer from 1 to 5, and if it is 2 or greater, Ar3 is the same or different,

[0132] The definitions of B1 to B4 are the same as those in the above chemical formula 1,

[0133] In the above chemical formula 1-2,

[0134] A1 to A4 are the same as or different from each other, and each independently represent hydrogen; deuterium; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R101R102 and -SiR101R102R103, or two or more adjacent groups are combined to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same or different and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0135] The definitions of B1 to B4 are the same as those in the above chemical formula 1,

[0136] The definitions of L1 to L3, Ar1, Ar2, n1 to n5 are the same as those in the above chemical formula 2.

[0137] In one embodiment of the present application, A1 to A4 of Chemical Formula 1-1 are the same as or different from each other, and each independently represent hydrogen; deuterium; a cyano group; a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C2 to C40 alkenyl group; a substituted or unsubstituted C2 to C40 alkynyl group; a substituted or unsubstituted C1 to C40 alkoxy group; a substituted or unsubstituted C3 to C40 cycloalkyl group; a substituted or unsubstituted C2 to C40 heterocycloalkyl group; a substituted or unsubstituted C6 to C40 aryl group; a substituted or unsubstituted C2 to C40 heteroaryl group; -P(=O)R101R102; -SiR101R102R103 and a group represented by the above chemical formula 2, or two or more adjacent groups are combined to form a substituted or unsubstituted C6 to C40 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C40 heterocycle, wherein R101, R102 and R103 are the same as or different from each other, and each independently represent a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group, wherein at least one of A1 to A4 may be a group represented by the above chemical formula 2.

[0138] In one embodiment of the present application, A1 to A4 of Chemical Formula 1-1 are the same as or different from each other, and each independently represent hydrogen; deuterium; a cyano group; a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C2 to C30 alkenyl group; a substituted or unsubstituted C2 to C30 alkynyl group; a substituted or unsubstituted C1 to C30 alkoxy group; a substituted or unsubstituted C3 to C30 cycloalkyl group; a substituted or unsubstituted C2 to C30 heterocycloalkyl group; a substituted or unsubstituted C6 to C30 aryl group; a substituted or unsubstituted C2 to C30 heteroaryl group; -P(=O)R101R102; -SiR101R102R103 and a group represented by the above chemical formula 2, or two or more adjacent groups are combined to form a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C30 heterocycle, wherein R101, R102 and R103 are the same as or different from each other, and each independently represent a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group, wherein at least one of A1 to A4 may be a group represented by the above chemical formula 2.

[0139] In one embodiment of the present application, A1 to A4 of Chemical Formula 1-1 are the same as or different from each other, and each independently represent hydrogen; deuterium; a cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C2 to C20 alkenyl group; a substituted or unsubstituted C2 to C20 alkynyl group; a substituted or unsubstituted C1 to C20 alkoxy group; a substituted or unsubstituted C3 to C20 cycloalkyl group; a substituted or unsubstituted C2 to C20 heterocycloalkyl group; a substituted or unsubstituted C6 to C20 aryl group; a substituted or unsubstituted C2 to C20 heteroaryl group; A group consisting of groups represented by the above chemical formula 2, or two or more adjacent groups bonded to each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C20 heterocycle, wherein at least one of the above A1 to A4 may be a group represented by the above chemical formula 2.

[0140] In one embodiment of the present application, A1 to A4 of Chemical Formula 1-1 are the same as or different from each other, and each independently represent hydrogen; deuterium; a cyano group; a substituted or unsubstituted C1 to C10 alkyl group; a substituted or unsubstituted C2 to C10 alkenyl group; a substituted or unsubstituted C2 to C10 alkynyl group; a substituted or unsubstituted C1 to C10 alkoxy group; a substituted or unsubstituted C3 to C10 cycloalkyl group; a substituted or unsubstituted C2 to C10 heterocycloalkyl group; a substituted or unsubstituted C6 to C10 aryl group; a substituted or unsubstituted C2 to C10 heteroaryl group; A group consisting of groups represented by the above chemical formula 2, or two or more adjacent groups bonded to each other to form a substituted or unsubstituted C6 to C10 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C10 heterocycle, wherein at least one of the above A1 to A4 may be a group represented by the above chemical formula 2.

[0141] In one embodiment of the present application, A1 to A4 of Chemical Formula 1-1 are the same as or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; and a group represented by Chemical Formula 2, and at least one of A1 to A4 may be a group represented by Chemical Formula 2.

[0142] In one embodiment of the present application, A1 of chemical formula 1-1 is a group represented by the chemical formula 2, and A2 to A4 are the same as or different from each other, and may each independently be hydrogen or deuterium.

[0143] In one embodiment of the present application, A2 of Chemical Formula 1-1 is a group represented by Chemical Formula 2, and A1, A3 and A4 are the same as or different from each other, and may each independently be hydrogen or deuterium.

[0144] In one embodiment of the present application, A3 of Chemical Formula 1-1 is a group represented by Chemical Formula 2, and A1, A2 and A4 are the same as or different from each other, and may each independently be hydrogen or deuterium.

[0145] In one embodiment of the present application, A4 of Chemical Formula 1-1 is a group represented by Chemical Formula 2, and A1 to A3 are the same as or different from each other, and may each independently be hydrogen or deuterium.

[0146] In one embodiment of the present application, L4 in chemical formula 1-1 may be the same as or different from each other, and may each independently be a single bond; a substituted or unsubstituted C6 to C40 arylene group; or a substituted or unsubstituted C2 to C40 heteroarylene group.

[0147] In one embodiment of the present application, L4 in chemical formula 1-1 may be the same as or different from each other, and may each independently be a single bond; a substituted or unsubstituted C6 to C30 arylene group; or a substituted or unsubstituted C2 to C30 heteroarylene group.

[0148] In one embodiment of the present application, L4 in chemical formula 1-1 may be the same as or different from each other, and may each independently be a single bond; a substituted or unsubstituted C6 to C20 arylene group; or a substituted or unsubstituted C2 to C20 heteroarylene group.

[0149] In one embodiment of the present application, L4 in chemical formula 1-1 may be the same as or different from each other, and may each independently be a single bond; a substituted or unsubstituted C6 to C10 arylene group; or a substituted or unsubstituted C2 to C10 heteroarylene group.

[0150] In one embodiment of the present application, L4 in Chemical Formula 1-1 may be the same as or different from each other, and may each independently be a single bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted terphenylene group; or a substituted or unsubstituted naphthylene group.

[0151] In one embodiment of the present application, Ar3 in chemical formula 1-1 may be the same as or different from each other, and may each independently be a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0152] In one embodiment of the present application, Ar3 in chemical formula 1-1 may be the same as or different from each other, and may each independently be a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0153] In one embodiment of the present application, Ar3 in chemical formula 1-1 may be the same as or different from each other, and may each independently be a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0154] In one embodiment of the present application, Ar3 in chemical formula 1-1 may be the same as or different from each other, and may each independently be a substituted or unsubstituted C6 to C10 aryl group; or a substituted or unsubstituted C2 to C10 heteroaryl group.

[0155] In one embodiment of the present application, Ar3 of Chemical Formula 1-1 may be the same as or different from each other, and each independently be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted triphenylenyl group; a substituted or unsubstituted dimethylfluorenyl group; a substituted or unsubstituted diphenylfluorenyl group; a substituted or unsubstituted spirobifluorenyl group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group.

[0156] In one embodiment of the present application, B1 to B4 of Chemical Formula 1-1 are the same as or different from each other, and each independently represent hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C2 to C40 alkenyl group; a substituted or unsubstituted C2 to C40 alkynyl group; a substituted or unsubstituted C1 to C40 alkoxy group; a substituted or unsubstituted C3 to C40 cycloalkyl group; a substituted or unsubstituted C2 to C40 heterocycloalkyl group; a substituted or unsubstituted C6 to C40 aryl group; a substituted or unsubstituted C2 to C40 heteroaryl group; -P(=O)R101R102 and -SiR101R102R103, or two or more adjacent groups are combined to form a substituted or unsubstituted C6 to C40 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C40 heterocycle, wherein R101, R102 and R103 are the same or different, and each independently represent a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group, wherein at least two of B1 to B4 may be substituted or unsubstituted C1 to C40 alkyl groups.

[0157] In one embodiment of the present application, B1 to B4 of Chemical Formula 1-1 are the same as or different from each other, and each independently represent hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C2 to C30 alkenyl group; a substituted or unsubstituted C2 to C30 alkynyl group; a substituted or unsubstituted C1 to C30 alkoxy group; a substituted or unsubstituted C3 to C30 cycloalkyl group; a substituted or unsubstituted C2 to C30 heterocycloalkyl group; a substituted or unsubstituted C6 to C30 aryl group; a substituted or unsubstituted C2 to C30 heteroaryl group; -P(=O)R101R102 and -SiR101R102R103, or two or more adjacent groups are combined to form a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C30 heterocycle, wherein R101, R102 and R103 are the same as or different from each other, and each independently represent a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group, wherein at least two of B1 to B4 may be substituted or unsubstituted C1 to C30 alkyl groups.

[0158] In one embodiment of the present application, B1 to B4 of Chemical Formula 1-1 are the same as or different from each other, and each independently represent hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C2 to C20 alkenyl group; a substituted or unsubstituted C2 to C20 alkynyl group; a substituted or unsubstituted C1 to C20 alkoxy group; a substituted or unsubstituted C3 to C20 cycloalkyl group; a substituted or unsubstituted C2 to C20 heterocycloalkyl group; a substituted or unsubstituted C6 to C20 aryl group; And is selected from the group consisting of a substituted or unsubstituted C2 to C20 heteroaryl group, or two or more adjacent groups are combined with each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C20 heterocycle, and at least two of the B1 to B4 may be a substituted or unsubstituted C1 to C20 alkyl group.

[0159] In one embodiment of the present application, B1 to B4 of Chemical Formula 1-1 are the same as or different from each other, and are each independently hydrogen; deuterium; or a substituted or unsubstituted C1 to C10 alkyl group, and at least two of B1 to B4 may be substituted or unsubstituted C1 to C10 alkyl groups.

[0160] In one embodiment of the present application, B1 to B4 of Chemical Formula 1-1 may be the same as or different from each other, and may each independently be hydrogen; deuterium; a substituted or unsubstituted isopropyl group; or a substituted or unsubstituted tert-butyl group, and at least two of B1 to B4 may be a substituted or unsubstituted isopropyl group; or a substituted or unsubstituted tert-butyl group.

[0161] In one embodiment of the present application, B1 to B4 of Chemical Formula 1-1 may be the same as or different from each other, and may each independently be hydrogen; deuterium; a substituted or unsubstituted isopropyl group; or a substituted or unsubstituted tert-butyl group.

[0162] In one embodiment of the present application, B1 and B2 in chemical formula 1-1 may be the same as or different from each other, and may each independently be a substituted or unsubstituted isopropyl group; or a substituted or unsubstituted tert-butyl group, and B3 and B4 may be the same as or different from each other, and may each independently be hydrogen; or deuterium.

[0163] In one embodiment of the present application, B1 and B3 of Chemical Formula 1-1 may be the same as or different from each other, and may each independently be a substituted or unsubstituted isopropyl group; or a substituted or unsubstituted tert-butyl group, and B2 and B4 may be the same as or different from each other, and may each independently be hydrogen; or deuterium.

[0164] In one embodiment of the present application, B1 and B4 of Chemical Formula 1-1 may be the same as or different from each other, and may each independently be a substituted or unsubstituted isopropyl group; or a substituted or unsubstituted tert-butyl group, and B2 and B3 may be the same as or different from each other, and may each independently be hydrogen; or deuterium.

[0165] In one embodiment of the present application, B2 and B3 in Chemical Formula 1-1 may be the same as or different from each other, and may each independently be a substituted or unsubstituted isopropyl group; or a substituted or unsubstituted tert-butyl group, and B1 and B4 may be the same as or different from each other, and may each independently be hydrogen; or deuterium.

[0166] In one embodiment of the present application, B2 and B4 in Chemical Formula 1-1 may be the same as or different from each other, and may each independently be a substituted or unsubstituted isopropyl group; or a substituted or unsubstituted tert-butyl group, and B1 and B3 may be the same as or different from each other, and may each independently be hydrogen; or deuterium.

[0167] In one embodiment of the present application, B3 and B4 in Chemical Formula 1-1 may be the same as or different from each other, and may each independently be a substituted or unsubstituted isopropyl group; or a substituted or unsubstituted tert-butyl group, and B1 and B2 may be the same as or different from each other, and may each independently be hydrogen; or deuterium.

[0168] In one embodiment of the present application, A1 to A4 of Chemical Formula 1-2 are the same as or different from each other, and each independently represent hydrogen; deuterium; a cyano group; a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C2 to C40 alkenyl group; a substituted or unsubstituted C2 to C40 alkynyl group; a substituted or unsubstituted C1 to C40 alkoxy group; a substituted or unsubstituted C3 to C40 cycloalkyl group; a substituted or unsubstituted C2 to C40 heterocycloalkyl group; a substituted or unsubstituted C6 to C40 aryl group; a substituted or unsubstituted C2 to C40 heteroaryl group; -P(=O)R101R102 and -SiR101R102R103, or two or more adjacent groups are combined to form a substituted or unsubstituted C6 to C40 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C40 heterocycle, wherein R101, R102 and R103 are the same or different, and each independently represent a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0169] In one embodiment of the present application, A1 to A4 of Chemical Formula 1-2 are the same as or different from each other, and each independently represent hydrogen; deuterium; a cyano group; a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C2 to C30 alkenyl group; a substituted or unsubstituted C2 to C30 alkynyl group; a substituted or unsubstituted C1 to C30 alkoxy group; a substituted or unsubstituted C3 to C30 cycloalkyl group; a substituted or unsubstituted C2 to C30 heterocycloalkyl group; a substituted or unsubstituted C6 to C30 aryl group; a substituted or unsubstituted C2 to C30 heteroaryl group; -P(=O)R101R102 and -SiR101R102R103, or two or more adjacent groups are combined to form a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C30 heterocycle, wherein R101, R102 and R103 are the same or different, and each independently represent a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0170] In one embodiment of the present application, A1 to A4 of Chemical Formula 1-2 are the same as or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; a cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C2 to C20 alkenyl group; a substituted or unsubstituted C2 to C20 alkynyl group; a substituted or unsubstituted C1 to C20 alkoxy group; a substituted or unsubstituted C3 to C20 cycloalkyl group; a substituted or unsubstituted C2 to C20 heterocycloalkyl group; a substituted or unsubstituted C6 to C20 aryl group and a substituted or unsubstituted C2 to C20 heteroaryl group, or two or more adjacent groups may combine with each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C20 heterocycle.

[0171] In one embodiment of the present application, A1 to A4 of Chemical Formula 1-2 are the same as or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; a cyano group; a substituted or unsubstituted C1 to C10 alkyl group; a substituted or unsubstituted C2 to C10 alkenyl group; a substituted or unsubstituted C2 to C10 alkynyl group; a substituted or unsubstituted C1 to C10 alkoxy group; a substituted or unsubstituted C3 to C10 cycloalkyl group; a substituted or unsubstituted C2 to C10 heterocycloalkyl group; a substituted or unsubstituted C6 to C10 aryl group and a substituted or unsubstituted C2 to C10 heteroaryl group, or two or more adjacent groups may combine with each other to form a substituted or unsubstituted C6 to C10 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C10 heterocycle.

[0172] In one embodiment of the present application, A1 to A4 of Chemical Formula 1-2 may be the same as or different from each other, and may each independently be hydrogen or deuterium.

[0173] In one embodiment of the present application, L1 to L3 of Chemical Formula 1-2 may be the same as or different from each other, and may each independently be a single bond; a substituted or unsubstituted C6 to C40 arylene group; or a substituted or unsubstituted C2 to C40 heteroarylene group.

[0174] In one embodiment of the present application, L1 to L3 of Chemical Formula 1-2 may be the same as or different from each other, and may each independently be a single bond; a substituted or unsubstituted C6 to C30 arylene group; or a substituted or unsubstituted C2 to C30 heteroarylene group.

[0175] In one embodiment of the present application, L1 to L3 of Chemical Formula 1-2 may be the same as or different from each other, and may each independently be a single bond; or a substituted or unsubstituted C6 to C20 arylene group.

[0176] In one embodiment of the present application, L1 to L3 of Chemical Formula 1-2 may be the same as or different from each other, and may each independently be a single bond; a substituted or unsubstituted C6 to C10 arylene group; or a substituted or unsubstituted C2 to C10 heteroarylene group.

[0177] In one embodiment of the present application, L1 to L3 of Chemical Formula 1-2 may be the same as or different from each other, and may each independently be a single bond; or a substituted or unsubstituted C6 to C10 arylene group.

[0178] In one embodiment of the present application, L1 to L3 of Chemical Formula 1-2 may be the same as or different from each other, and may each independently be a single bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted terphenylene group; or a substituted or unsubstituted naphthylene group.

[0179] In one embodiment of the present application, Ar1 and Ar2 in chemical formula 1-2 may be the same as or different from each other, and may each independently be a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0180] In one embodiment of the present application, Ar1 and Ar2 in chemical formula 1-2 may be the same as or different from each other, and may each independently be a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0181] In one embodiment of the present application, Ar1 and Ar2 in chemical formula 1-2 may be the same as or different from each other, and may each independently be a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0182] In one embodiment of the present application, Ar1 and Ar2 in chemical formula 1-2 may be the same as or different from each other, and may each independently be a substituted or unsubstituted C6 to C10 aryl group; or a substituted or unsubstituted C2 to C10 heteroaryl group.

[0183] In one embodiment of the present application, Ar1 and Ar2 of Chemical Formula 1-2 may be the same as or different from each other, and may each independently be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted triphenylenyl group; a substituted or unsubstituted dimethylfluorenyl group; a substituted or unsubstituted diphenylfluorenyl group; a substituted or unsubstituted spirobifluorenyl group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group.

[0184] In one embodiment of the present application, Ar1 to Ar3 may be represented by either the following chemical formula 3 or chemical formula 4.

[0185] [Chemical Formula 3]

[0186]

[0187] [Chemical Formula 4]

[0188]

[0189] In the above chemical formulas 3 and 4,

[0190] X1 is O, S or CRaRb,

[0191] Ar4 is a substituted or unsubstituted C6 to C60 aryl group,

[0192] R1, R2, Ra and Rb are the same as or different from each other, and each independently represent hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R101R102 and -SiR101R102R103, or two or more adjacent groups are combined to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same or different and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0193] n8 is an integer from 0 to 4, and if it is 2 or greater, R1 is equal or different,

[0194] n9 is an integer from 0 to 3, and if it is 2 or greater, R2 is equal or different.

[0195] In one embodiment of the present application, X1 of chemical formula 3 may be O.

[0196] In one embodiment of the present application, X1 of chemical formula 3 may be S.

[0197] In one embodiment of the present application, X1 of chemical formula 3 may be CRaRb.

[0198] In one embodiment of the present application, Ar4 in chemical formula 4 may be a substituted or unsubstituted C6 to C40 aryl group.

[0199] In one embodiment of the present application, Ar4 in chemical formula 4 may be a substituted or unsubstituted C6 to C30 aryl group.

[0200] In one embodiment of the present application, Ar4 in chemical formula 4 may be a substituted or unsubstituted C6 to C20 aryl group.

[0201] In one embodiment of the present application, Ar4 in chemical formula 4 may be a substituted or unsubstituted C6 to C10 aryl group.

[0202] In one embodiment of the present application, Ar4 of chemical formula 4 may be selected from a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; or a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrenyl group; or a substituted or unsubstituted triphenylenyl group.

[0203] In one embodiment of the present application, R1, R2, Ra and Rb are the same as or different from each other, and each independently hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C2 to C40 alkenyl group; a substituted or unsubstituted C2 to C40 alkynyl group; a substituted or unsubstituted C1 to C40 alkoxy group; a substituted or unsubstituted C3 to C40 cycloalkyl group; a substituted or unsubstituted C2 to C40 heterocycloalkyl group; a substituted or unsubstituted C6 to C40 aryl group; a substituted or unsubstituted C2 to C40 heteroaryl group; -P(=O)R101R102 and -SiR101R102R103, or two or more adjacent groups are combined to form a substituted or unsubstituted C6 to C40 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C40 heterocycle, wherein R101, R102 and R103 are the same or different, and each independently represent a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0204] In one embodiment of the present application, R1, R2, Ra and Rb are the same as or different from each other, and each independently hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C2 to C30 alkenyl group; a substituted or unsubstituted C2 to C30 alkynyl group; a substituted or unsubstituted C1 to C30 alkoxy group; a substituted or unsubstituted C3 to C30 cycloalkyl group; a substituted or unsubstituted C2 to C30 heterocycloalkyl group; a substituted or unsubstituted C6 to C30 aryl group; a substituted or unsubstituted C2 to C30 heteroaryl group; -P(=O)R101R102 and -SiR101R102R103, or two or more adjacent groups are combined to form a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C30 heterocycle, wherein R101, R102 and R103 are the same or different, and each independently represent a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0205] In one embodiment of the present application, R1, R2, Ra and Rb are the same as or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; a cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C2 to C20 alkenyl group; a substituted or unsubstituted C2 to C20 alkynyl group; a substituted or unsubstituted C1 to C20 alkoxy group; a substituted or unsubstituted C3 to C20 cycloalkyl group; a substituted or unsubstituted C2 to C20 heterocycloalkyl group; a substituted or unsubstituted C6 to C20 aryl group; and a substituted or unsubstituted C2 to C20 heteroaryl group, or two or more adjacent groups may combine with each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C20 heterocycle.

[0206] In one embodiment of the present application, R1, R2, Ra and Rb are the same as or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; a cyano group; a substituted or unsubstituted C1 to C10 alkyl group; a substituted or unsubstituted C2 to C10 alkenyl group; a substituted or unsubstituted C2 to C10 alkynyl group; a substituted or unsubstituted C1 to C10 alkoxy group; a substituted or unsubstituted C3 to C10 cycloalkyl group; a substituted or unsubstituted C2 to C10 heterocycloalkyl group; a substituted or unsubstituted C6 to C10 aryl group; and a substituted or unsubstituted C2 to C10 heteroaryl group, or two or more adjacent groups may combine with each other to form a substituted or unsubstituted C6 to C10 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C10 heterocycle.

[0207] In one embodiment of the present application, R1, R2, Ra and Rb may be the same as or different from each other, and may each independently be hydrogen; deuterium; a substituted or unsubstituted methyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted terphenyl group, and two or more adjacent groups may combine with each other to form a substituted or unsubstituted C6 to C10 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C10 heterocycle.

[0208] In one embodiment of the present application, the heterocyclic compound represented by the chemical formula 1 may not contain deuterium as a substituent, or the content of deuterium may be, for example, 1% or more, 5% or more, 10% or more, 15% or more, 20% or more, 25% or more, 30% or more, 35% or more, 40% or more, 45% or more, or 50% or more, and may be 100% or less, 95% or less, 90% or less, 85% or less, 80% or less, 75% or less, 70% or less, 65% or less, or 60% or less, based on the total number of hydrogen atoms and deuterium atoms.

[0209] In one embodiment of the present application, the heterocyclic compound represented by the chemical formula 1 may not contain deuterium, or may have a deuterium content of 1% to 100% based on the total number of hydrogen atoms and deuterium atoms.

[0210] In one embodiment of the present application, the heterocyclic compound represented by the chemical formula 1 may not contain deuterium, or may have a deuterium content of 10% to 100% based on the total number of hydrogen atoms and deuterium atoms.

[0211] In one embodiment of the present application, the heterocyclic compound represented by the chemical formula 1 may not contain deuterium, or may have a deuterium content of 20% to 90% based on the total number of hydrogen atoms and deuterium atoms.

[0212] In one embodiment of the present application, the heterocyclic compound represented by the chemical formula 1 may not contain deuterium, or may have a deuterium content of 30% to 80% based on the total number of hydrogen atoms and deuterium atoms.

[0213] In one embodiment of the present application, the heterocyclic compound represented by the chemical formula 1 may not contain deuterium, or may have a deuterium content of 40% to 70% based on the total number of hydrogen atoms and deuterium atoms.

[0214] In one embodiment of the present application, the heterocyclic compound represented by the chemical formula 1 may not contain deuterium, or may have a deuterium content of 50% to 60% based on the total number of hydrogen atoms and deuterium atoms.

[0215] In one embodiment of the present application, the chemical formula 1 provides a heterocyclic compound represented by any one of the compounds below. In addition, in one embodiment of the present application, the compounds below are only examples, and are not limited thereto, and other compounds included in chemical formula 1 that include additional substituents may be included.

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228] In addition, by introducing various substituents into the structure of the above chemical formula 1, it is possible to synthesize compounds having the unique characteristics of the introduced substituents. For example, by introducing substituents mainly used in hole injection layer materials, hole transport materials, light-emitting layer materials, electron transport layer materials, and charge generation layer materials used in the manufacture of organic light-emitting devices into the core structure, it is possible to synthesize materials that satisfy the conditions required for each organic layer.

[0229] In addition, by introducing various substituents into the structure of the above chemical formula 1, it is possible to finely control the energy band gap, while improving the properties at the interface between organic substances and diversifying the uses of the material.

[0230] Another embodiment of the present invention provides an organic light-emitting device comprising a heterocyclic compound represented by the above chemical formula 1. The "organic light-emitting device" may be expressed by terms such as "organic light-emitting diode", "OLED (Organic Light Emitting Diodes)", "OLED device", and "organic electroluminescent device".

[0231] In one embodiment of the present application, an organic light-emitting device is provided, comprising: a first electrode; a second electrode provided opposite the first electrode; and one or more organic layers provided between the first electrode and the second electrode; wherein at least one of the organic layers includes a heterocyclic compound represented by the chemical formula 1.

[0232] In one embodiment of the present application, the first electrode may be an anode, and the second electrode may be a cathode.

[0233] In another embodiment, the first electrode may be a cathode and the second electrode may be an anode.

[0234] In one embodiment of the present application, the organic light-emitting device may be a blue organic light-emitting device, and the heterocyclic compound according to the chemical formula 1 may be used as a material for the blue organic light-emitting device. For example, the heterocyclic compound represented by the chemical formula 1 may be included in a hole transport layer or a hole transport auxiliary layer of the blue organic light-emitting device.

[0235] In one embodiment of the present application, the organic light-emitting device may be a green organic light-emitting device, and the heterocyclic compound represented by the chemical formula 1 may be used as a material for the green organic light-emitting device. For example, the heterocyclic compound represented by the chemical formula 1 may be included in a hole transport layer or a hole transport auxiliary layer of the green organic light-emitting device.

[0236] In one embodiment of the present application, the organic light-emitting device may be a red organic light-emitting device, and the heterocyclic compound represented by the chemical formula 1 may be used as a material for the red organic light-emitting device. For example, the heterocyclic compound represented by the chemical formula 1 may be included in a hole transport layer or a hole transport auxiliary layer of the red organic light-emitting device.

[0237] The specific details of the heterocyclic compound represented by the above chemical formula 1 are the same as described above.

[0238] 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 aforementioned heterocyclic compound.

[0239] The above heterocyclic compound 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, inkjet printing, screen printing, spraying, roll coating, etc.

[0240] The organic layer of the organic light-emitting device of the present invention 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, the organic light-emitting device of the present invention 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, etc. as the organic layers. However, the structure of the organic light-emitting device is not limited thereto and may include a smaller number of organic layers.

[0241] In the organic light-emitting device of the present specification, the organic layer may include a hole transport layer, and the hole transport layer may include a heterocyclic compound represented by the chemical formula 1.

[0242] In the organic light-emitting device of the present specification, the organic layer includes a hole transport auxiliary layer, and the hole transport auxiliary layer may include a heterocyclic compound represented by the chemical formula 1.

[0243] The organic light-emitting device of the present invention may further include one or two or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron injection layer, an electron transport layer, a battery blocking layer, and a hole blocking layer.

[0244] The stacking order of electrodes and organic layers of an organic light-emitting device according to one embodiment of the present invention is illustrated in FIGS. 1 to 3. However, the scope of the present application is not intended to be limited by these drawings, and the structure of an organic light-emitting device known in the art may also be applied to the present application.

[0245] According to FIG. 1, an organic light-emitting device is illustrated in which an anode (200), an organic layer (300), and a cathode (400) are sequentially laminated on a substrate (100). However, the present invention is not limited to this structure, and an organic light-emitting device in which a cathode, an organic layer, and an anode are sequentially laminated on a substrate, as shown in FIG. 2, may also be implemented.

[0246] Fig. 3 illustrates a case where the organic layer is multilayered. The organic light-emitting device according to Fig. 3 includes a hole injection layer (301), a hole transport layer (302), a light-emitting layer (303), a hole blocking layer (304), an electron transport layer (305), and an electron injection layer (306). However, the scope of the present application is not limited by such a laminated structure, and, if necessary, the remaining layers except for the light-emitting layer may be omitted, and other necessary functional layers may be further added.

[0247] In one embodiment of the present invention, a method for manufacturing an organic light-emitting device is provided, comprising the steps of: preparing a substrate; forming a first electrode on the substrate; forming one or more organic layers on the first electrode; and forming a second electrode on the organic layer, wherein the step of forming the organic layer includes forming one or more organic layers using an organic layer composition according to one embodiment of the present invention.

[0248] In one embodiment of the present invention, the step of forming the organic layer may be to pre-mix the heterocyclic compound represented by the chemical formula 1 and form it using a thermal vacuum deposition method.

[0249] The above pre-mixed means that the materials are first mixed and placed in one supply source before depositing the heterocyclic compound represented by the above chemical formula 1 on the organic layer.

[0250] The pre-mixed material may be referred to as a composition for an organic layer according to one embodiment of the present application.

[0251] The organic layer including the heterocyclic compound represented by the above chemical formula 1 may additionally include other substances as needed.

[0252] In an organic light-emitting device according to one embodiment of the present invention, materials other than the heterocyclic compound represented by the above chemical formula 1 are exemplified below, but these are only for exemplification and are not intended to limit the scope of the present application, and may be replaced with materials known in the art.

[0253] Materials having a relatively large work function can be used as the anode material, and transparent conductive oxides, metals, or conductive polymers can be used. Specific examples of the anode material 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.

[0254] Materials with relatively low work functions can be used as cathode materials, and metals, metal oxides, or conductive polymers can be used. Specific examples of the cathode materials 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.

[0255] As the hole injection layer material, a known hole injection layer material may be used, for example, a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429, or a starburst amine derivative described in the literature [Advanced Material, 6, p. 677 (1994)], such as tris(4-carbazoyl-9-ylphenyl)amine (TCTA), 4,4',4"-tri[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB), a soluble conductive polymer such as polyaniline / dodecylbenzenesulfonic acid, or Poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate), polyaniline / camphor sulfonic acid, or polyaniline / poly(4-styrenesulfonate) can be used.

[0256] Pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, etc. can be used as hole transport layer materials, and low molecular weight or high molecular weight materials can also be used.

[0257] As the electron transport layer material, metal complexes of oxadiazole derivatives, anthraquinodimethane and derivatives thereof, benzoquinone and derivatives thereof, naphthoquinone and derivatives thereof, anthraquinone and derivatives thereof, tetracyanoanthraquinodimethane and derivatives thereof, fluorenone derivatives, diphenyldicyanoethylene and derivatives thereof, diphenoquinone derivatives, 8-hydroxyquinoline and derivatives thereof, etc. can be used, and not only low molecular weight substances but also high molecular weight substances can be used.

[0258] LiF is typically used as an electron injection layer material in the art, but the present application is not limited thereto.

[0259] Red, green, or blue light-emitting materials can be used as the light-emitting layer material, and if necessary, two or more light-emitting materials can be mixed and used. At this time, two or more light-emitting materials can be deposited and used as individual sources, or can be premixed and deposited and used as a single source. In addition, a fluorescent material can be used as the light-emitting layer material, but it can also be used as a phosphorescent material. A material that emits light by combining holes and electrons injected from the anode and cathode, respectively, can be used as the light-emitting layer material, but materials in which both the host material and the dopant material participate in light emission can also be used.

[0260] When using a mixture of host materials for the light-emitting layer, hosts of the same series may be mixed and used, or hosts of different series may be mixed and used. For example, two or more types of materials, either n-type host materials or p-type host materials, may be selected and used as the host material for the light-emitting layer.

[0261] An organic light-emitting device according to one embodiment of the present invention may be a front-emitting, rear-emitting, or double-sided light-emitting device depending on the material used.

[0262] The heterocyclic compound according to one embodiment of the present invention can function in organic electronic devices, including organic solar cells, organic photoconductors, organic transistors, etc., using a principle similar to that applied to organic light-emitting devices.

[0263] Hereinafter, preferred examples are presented to help understand the present invention, but the following examples are provided only to make it easier to understand the present invention and the present invention is not limited thereto.

[0264]

[0265] <Manufacturing Example>

[0266] <Manufacturing Example 1> Preparation of compound 001

[0267]

[0268]

[0269] 1) Preparation of compound 001-P3

[0270] Compound 2-bromo-1-chloro-3-nitrobenzene (30 g, 0.1269 mol) and (2,3-di-tert-butylphenyl)boronic acid (35.65 g, 0.1523 mol) were dissolved in 500 mL of toluene and 100 mL of distilled water, and Pd(PPh3)4 (7.3 g, 0.0063 mol) and K2CO3 (35.07 g, 0.2538 mol) were added and stirred under reflux for 6 hours. After completion of the reaction, the mixture was extracted with dichloromethane and distilled water, and the organic layer was dried over anhydrous MgSO4 and the solvent was removed using a rotary evaporator. The residue was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain compound 001-P3 (33 g, 75%).

[0271]

[0272] 2) Preparation of compound 001-P2

[0273] Compound 001-P3 (33 g, 0.0954 mol) was dissolved in 400 mL of 1,2-Dichlorobenzene, and PPh3 (62.56 g, 0.2385 mol) was slowly added dropwise, followed by reflux stirring for 3 hours. After completion of the reaction, distilled water was slowly added, followed by extraction with dichloromethane, and the organic layer was dried over anhydrous MgSO4 and the solvent was removed using a rotary evaporator to obtain compound 001-P2 (20 g, 67%).

[0274]

[0275] 3) Preparation of compound 001-P1

[0276] Compound 001-P2 (20 g, 0.0637 mol) and Iodobenzene (14.3 g, 0.0701 mol) were dissolved in 300 mL of toluene, and then Pd2(dba)3 (2.92 g, 0.0032 mol) and NaOH were added. (5.10 g, 0.1274 mol), sphos(Dicyclohexyl(2′,6′-dimethoxy[1,1′-biphenyl]-2-yl)phosphane) (3.92 g, 0.0096 mol) were added and stirred under reflux for 6 hours. After the reaction was completed, dichloromethane was added to the reaction solution to dissolve it, extracted with distilled water, and the organic layer was dried over anhydrous MgSO4, and the solvent was removed using a rotary evaporator. Then, the mixture was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain compound 001-P1 (15 g, 60%).

[0277]

[0278] 4) Preparation of compound 001

[0279] Compound 001-P1 (15 g, 0.0385 mol) and diphenylamine (7.16 g, 0.0423 mol) were dissolved in 150 mL of toluene, and then Pd2(dba)3 (1.76 g, 0.0019 mol), xphos(Dicyclohexyl[2′,4′,6′-tris(propan-2-yl)[1,1′'-biphenyl]-2-yl]phosphane) (2.75 g, 0.0058 mol), t-BuONa (7.39 g, 0.0769 mol) was added and stirred under reflux for 2 hours. After the reaction was completed, dichloromethane was added to the reaction solution to dissolve it, extracted with distilled water, and the organic layer was dried over anhydrous MgSO4, and the solvent was removed using a rotary evaporator. Then, the mixture was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain compound 001 (75 g, 75%).

[0280]

[0281] <Manufacturing Example 2> Preparation of compounds 16, 30, 49, 66, 75, 83, 91, 120, and 121

[0282] Compounds 16, 30, 49, 66, 75, 83, 91, 120, and 121 were synthesized in the same manner as in Manufacturing Example 1, except that Compound A in Table 1 was used instead of 2-bromo-1-chloro-3-nitrobenzene, Compound B was used instead of (2,3-di-tert-butylphenyl)boronic acid, Compound C was used instead of iodobenzene, and Compound D was used instead of diphenylamine.

[0283]

[0284]

[0285]

[0286]

[0287] <Manufacturing Example 3> Preparation of compound 147

[0288]

[0289] 1) Preparation of compound 147-P2

[0290] Compound 1-bromo-2-nitrobenzene (15 g, 0.0743 mol) and (2,3-di-tert-butylphenyl)boronic acid (20.86 g, 0.0891 mol) were dissolved in 300 mL of toluene and 60 mL of distilled water, and Pd(PPh3)4 (4.29 g, 0.00.7 mol) and K2CO3 (20.53 g, 0.1485 mol) were added and stirred under reflux for 6 hours. After completion of the reaction, the mixture was extracted with dichloromethane and distilled water, and the organic layer was dried over anhydrous MgSO4 and the solvent was removed using a rotary evaporator. The residue was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain compound 147-P2 (17 g, 74%).

[0291]

[0292] 2) Preparation of compound 147-P1

[0293] Compound 147-P2 (17 g, 0.0546 mol) was dissolved in 250 mL of 1,2-dichlorobenzene, and PPh3 (35.8 g, 0.1365 mol) was slowly added dropwise, followed by reflux stirring for 3 hours. After completion of the reaction, distilled water was slowly added, followed by extraction with dichloromethane, and the organic layer was dried over anhydrous MgSO4 and the solvent was removed using a rotary evaporator to obtain compound 147-P1 (10 g, 66%).

[0294]

[0295] 3) Preparation of compound 147

[0296] Compound 147-P1 (10 g, 0.0358 mol) and N-([1,1'-biphenyl]-4-yl)-N-(4-bromophenyl)-[1,1'-biphenyl]-4-amine (18.75 g, 0.0394 mol) were dissolved in 150 mL of toluene, and then Pd2(dba)3 (1.64 g, 0.0018 mol), xphos (2.56 g, 0.0054 mol), and t-BuONa (6.88 g, 0.0716 mol) was added and stirred under reflux for 3 hours. After the reaction was completed, MC was added to the reaction solution to dissolve it, extracted with distilled water, and the organic layer was dried over anhydrous MgSO4, and the solvent was removed using a rotary evaporator. Then, the mixture was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain compound 147 (15 g, 62%).

[0297]

[0298] <Manufacturing Example 4> Preparation of compounds 156, 164, and 179

[0299] Compounds 156, 164, and 179 were synthesized in the same manner as in Manufacturing Example 3, except that Compound E was used instead of (2,3-di-tert-butylphenyl)boronic acid in Manufacturing Example 3, and Compound F was used instead of N-([1,1'-biphenyl]-4-yl)-N-(4-bromophenyl)-[1,1'-biphenyl]-4-amine.

[0300]

[0301]

[0302] <Manufacturing Example 5> Preparation of compound 038

[0303]

[0304] Compound 038-P1 (15 g, 0.0277 mol) and (4-(diphenylamino)phenyl)boronic acid (9.6 g, 0.0332 mol) were dissolved in 150 mL of toluene and 30 mL of distilled water, and Pd(PPh3)4 (1.6 g, 0.0014 mol) and K2CO3 (7.65 g, 0.0553 mol) were added, and the mixture was stirred under reflux for 6 hours. After completion of the reaction, the mixture was extracted with dichloromethane and distilled water, and the organic layer was dried over anhydrous MgSO4, and the solvent was removed using a rotary evaporator. The residue was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain compound 038 (15 g, 72%).

[0305]

[0306] <Manufacturing Example 6> Preparation of compounds 059 and 103

[0307] Compounds 059 and 103 were synthesized in the same manner as in Manufacturing Example 5, except that compound G was used instead of 033-P1 and compound H was used instead of (4-(diphenylamino)phenyl)boronic acid.

[0308]

[0309]

[0310]

[0311] <Manufacturing Example 7> Preparation of compound 181

[0312]

[0313] Add compound 181-P1 (10 g, 0.0148 mol), benzene-D6 (100 mL, 10T), and triflic acid (6.54 mL, 0.0741 mol) to a flask and stir at 60°C. After 4 hours, 300 mL of distilled water and NaHCO3 are added dropwise to terminate the reaction. Extract with dichloromethane and distilled water, dry the organic layer over anhydrous MgSO4, remove the solvent using a rotary evaporator, and purify the residue through silica gel using dichloromethane and hexane as a developing solvent to obtain compound 181 (10.2 g, 95%).

[0314]

[0315] <Manufacturing Example 8> Preparation of compounds 190 and 196

[0316] Compounds 190 and 196 were synthesized in the same manner as in Manufacturing Example 7, except that compound I was used instead of 181-P1 in Manufacturing Example 7.

[0317]

[0318]

[0319]

[0320] <Manufacturing Example 9> Preparation of compound 195

[0321]

[0322]

[0323] 1) Preparation of compound 195-P1

[0324] Add compound 195-P2 (10 g, 0.0198 mol), benzene-D6 (100 mL, 10T), and triflic acid (8.7 mL, 0.0988 mol) to a flask and stir at 60°C. After 4 hours, 300 mL of distilled water and NaHCO3 are added dropwise to terminate the reaction. Extract with dichloromethane and distilled water, dry the organic layer over anhydrous MgSO4, remove the solvent using a rotary evaporator, and purify the residue through silica gel using dichloromethane and hexane as a developing solvent to obtain compound 195-P1 (9.8 g, 96%).

[0325]

[0326] 2) Preparation of compound 195

[0327] Compound 195-P1 (9.8 g, 0.0189 mol) and N,9,9-triphenyl-9H-fluoren-2-amine (8.5 g, 0.0208 mol) were dissolved in 100 mL of toluene, and then Pd2(dba)3 (0.87 g, 0.0009 mol), xphos (1.35 g, 0.0028 mol), and t-BuONa (3.64 g, 0.0379 mol) was added and stirred under reflux for 3 hours. After completion of the reaction, the mixture was extracted with dichloromethane and distilled water, the organic layer was dried over anhydrous MgSO4, the solvent was removed using a rotary evaporator, and the residue was purified by passing it through silica gel using dichloromethane and hexane as a developing solvent to obtain compound 195 (12 g, 71%).

[0328]

[0329] <Manufacturing Example 10> Preparation of compound 198

[0330] Compound 198 was synthesized in the same manner as in Manufacturing Example 9, except that compound J was used instead of 195-P2 and compound K was used instead of N,9,9-triphenyl-9H-fluoren-2-amine.

[0331]

[0332]

[0333] The remaining compounds other than those described in Manufacturing Examples 1 to 10 and Tables 1 to 5 were also manufactured using the same method as described in the above Manufacturing Examples, and the results of their synthesis are shown in Tables 6 and 7 below. Table 6 1 The values ​​are measured by H NMR (CDCl3, 300 MHz), and Table 7 is measured by FD-mass spectrometry (FD-MS: Field desorption mass spectrometry).

[0334]

[0335] Compound number 1H NMR(CDCl3, 300MHz)1δ= 7.66-7.50 (6H, m), 7.33-7.24 (7H, m), 7.08-7.00 (7H, m), 1.35 (18H, s)16δ= 8.87 (1H, s), 8.45 (1H, d), 8.05 (1H, s), 7.93-7.91 (5H, m), 7.75 (4H, m), 7.59-7.25 (15H, m), 1.35 (18H, s)30δ= 8.01 (1H, s), 7.92-7.75 (9H, m), 7.55-7.28 (14H, m), 7.19-7.16 (5H, m), 1.69 (6H, s), 1.35 (18H, s)38δ= 8.31-8.30 (3H, m), 8.13 (1H, d), 7.90-7.89 (2H, d), 7.75 (4H, d), 7.55-7.37 (10H, m), 7.24-7.23 (5H, m), 7.08-7.00 (7H, m), 1.35-1.32 (18H, d)49δ= 8.15-8.11 (3H, m), 7.90-7.79 (3H, m), 7.66-7.52 (5H, m), 7.38-7.24 (8H, m), 7.08-7.00 (4H, m), 1.69 (6H, s), 1.35 (18H, s)59δ= 8.62 (1H, d), 8.22-8.09 (5H, m), 7.79-7.74 (6H, m), 7.60-7.41 (21H, m), 7.16 (1H, s), 2.88-2.87 (2H, m), 1.20-1.18 (12H, m)66δ= 8.03-8.01 (4H, m), 7.90-7.83 (3H, m), 7.75 (6H, m), 7.59-7.36 (20H, m), 6.48 (1H, d), 1.35 (18H, s)75δ= 8.98 (1H, d), 8.84 (1H, d), 8.39 (1H, d), 8.11 (1H, d), 7.90-7.85 (6H, m), 7.68-7.38 (11H, m), 7.28-7.18 (8H, m), 7.08-7.00 (4H, m), 6.40 (1H, d), 1.35 (18H, s)83δ= 8.98 (1H, d), 8.84 (1H, d), 8.39 (1H, d), 8.11-8.09 (2H, m), 7.90 (1H, d), 7.83 (1H, s), 7.75-7.37 (22H, m), 7.18-7.16 (2H, d), 6.40 (1H, d), 2.88-2.87 (2H, m), 1.20-1.18 (12H, m)91δ= 9.08-9.05 (2H, m), 8.33 (1H, d), 8.25 (1H, d), 7.94-7.90 (2H, m), 7.70-7.16 (25H, m), 6.40 (1H, d), 2.88 (2H, m), 1.69 (6H, s), 1.18 (12H, d)103δ= 8.62 (1H, d), 8.22 (1H, d), 7.90 (1H, d), 7.75-7.74 (5H, m), 7.55-7.28 (26H, m), 2.88 (2H, m), 1.69 (6H, s), 1.18 (12H, d)120δ= 8.45 (1H, d), 8.33 (1H, d), 7.96-7.85 (4H, m), 7.75-7.69 (3H, m), 7.56-7.25 (18H, m), 7.04 (1H, d), 2.88 (2H, m), 1.69 (6H, s), 1.18 (12H, d)121δ= 8.04-7.98 (2H, m), 7.90 (1H, d), 7.75 (2H, m), 7.67-7.66 (2H, m), 7.55-7.25 (19H, m), 7.03 (1H, d), 6.91 (1H, d), 1.69 (6H, s), 1.35 (18H, s)147δ= 8.55 (1H, d), 7.94 (1H, d), 7.75-7.69 (6H, m), 7.55-7.30 (19H, m), 7.16 (1H, m), 1.35 (18H, s)156δ= 8.55 (1H, d), 8.10 (1H, s), 7.94-7.86 (5H, m), 7.69 (2H, m), 7.55 (2H, m), 7.38-7.28 (10H, m), 7.16 (3H, m), 1.69 (12H, s), 1.35 (18H, s)164δ= 8.55 (1H, d), 8.21 (1H, s), 7.94-7.86 (3H, m), 7.75-7.68 (3H, m), 7.60-7.35 (20H, m), 7.61 (2H, m), 2.88 (2H, m), 1.69 (6H, s), 1.18 (12H, d)179δ= 8.55 (1H, d), 8.02 (1H, d), 7.94-7.85 (5H, m), 7.55-7.00 (23H, m), 2.88 (2H, m), 1.18 (12H, d)181No proton190No proton195δ= 7.90-7.86 (2H, m), 7.55 (1H, d), 7.47 (1H, s), 7.38-7.00 (18H, m), 1.69 (6H, s), 1.35 (18H, s)196δ= 7.24 (4H, m), 7.08-7.00 (6H, m), 2.88 (2H, m), 1.69 (6H, s), 1.18 (12H, d)198δ= 8.87 (1H, s), 8.05 (1H, s), 7.90-7.85 (3H, m), 7.55-7.52 (2H, m), 7.40-7.25 (5H, m), 1.69 (18H, s), 1.35 (18H, s).

[0336]

[0337] Compound number FD-MS Compound number FD-MS 1 m / z = 522.30 (C38H38N2 = 522.74) 120 m / z = 792.35 (C57H48N2S = 793.09) 16 m / z = 780.35 (C56H48N2S = 781.07) 121 m / z = 804.41 (C59H52N2O = 805.08) 30 m / z = 790.43 (C59H54N2 = 791.10) 147 m / z = 674.37 (C50H46N2 = 674.93) 38 m / z = 750.40 (C56H50N2 = 751.03) 156 m / z = 754.43 (C56H54N2=755.06)49m / z=688.38 (C51H48N2=688.96)164m / z=762.40 (C57H50N2=763.04)59m / z=772.38 (C58H48N2=773.04)179m / z=732.35 (C55H44N2=732.97)66m / z=800.41 (C60H52N2=801.09)181m / z=720.65 (C50D46N2=721.21)75m / z=860.41 (C65H52N2=861.14)190m / z=612.57 (C42D40N2=613.04)83m / z=746.37 (C56H46N2=747.00)195m / z=889.53 (C66H47D11N2=890.27)91m / z=810.40 (C61H50N2=811.08)196m / z=622.41 (C45H30D12N2=622.92)103m / z=838.43 (C63H52N2=839.14)198m / z=884.58 (C65H48D14N2=885.31)

[0338]

[0339] Experimental Example 1

[0340] 1) Fabrication of organic light-emitting devices

[0341] A glass substrate coated with a 1,500 Å thick ITO film was ultrasonically cleaned in distilled water. After the distilled water cleaning, it was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UVO for 5 minutes in a UV cleaner. Afterwards, the substrate was transferred to a plasma cleaner (PT), and plasma treated in a vacuum to remove the ITO work function and residual film, and then transferred to a thermal evaporation equipment for organic deposition.

[0342]

[0343] Then the vacuum level inside the chamber is 10 -6 After evacuating to 10 torr, a current was applied to the cell to evaporate 2-TNATA, thereby depositing a 600 Å thick hole injection layer on an ITO substrate. N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) was placed in another cell within the vacuum deposition equipment, and a current was applied to the cell to evaporate it, thereby depositing a 300 Å thick hole transport layer on the hole injection layer.

[0344]

[0345] On top of that, a light-emitting layer was thermally vacuum deposited as follows. The light-emitting layer was deposited with a compound of 9-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-9'-phenyl-3,3'-Bi-9H-carbazole as a host by 400 Å, and a green phosphorescent dopant was deposited by doping Ir(ppy)3 by 7%. After that, BCP was deposited with 60 Å as a hole-blocking layer, and Alq3 was deposited with 200 Å as an electron-transporting layer thereon. Finally, lithium fluoride (LiF) was deposited with a thickness of 10 Å on the electron-transporting layer to form an electron injection layer, and then an aluminum (Al) cathode was deposited with a thickness of 1,200 Å on the electron injection layer to form a cathode, thereby manufacturing an organic light-emitting device (hereinafter, Comparative Example 1).

[0346]

[0347] Meanwhile, all organic compounds required for manufacturing organic light-emitting devices are 10 for each material. -6 ~10 -8 It was purified by vacuum sublimation under 10 torr and used in the manufacture of organic light-emitting devices.

[0348] In addition, an organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that the compound described in Table 8 below was used instead of the compound NPB used in forming the hole transport layer in Comparative Example 1.

[0349]

[0350] 2) Driving voltage and luminous efficiency of organic electroluminescent devices

[0351] The electroluminescence (EL) characteristics of the organic light-emitting devices manufactured as described above were measured using M7000 from MaxScience, and the standard luminance was determined to be 6,000 cd / m using the lifespan measurement equipment (M6000) manufactured by MaxScience based on the measurement results. 2The lifespan T is the time it takes for the initial luminance to reach 95% of its original brightness. 95 (Unit: h, time) was measured. The results of measuring the driving voltage, luminous efficiency, and lifespan of the organic light-emitting device of the present invention as shown in the above measurement results are as shown in Table 8 below.

[0352] Compound Driving Voltage (V) Efficiency (cd / A) Lifespan (T) 95 ) Comparative Example 1 NPB 5.3484.22113 Comparative Example 2 Comparative Compound A 5.5989.9498 Comparative Example 3 Comparative Compound B 5.4896.2795 Comparative Example 4 Comparative Compound C 5.8987.8076 Comparative Example 5 Comparative Compound D 6.1285.4799 Comparative Example 6 Comparative Compound E 6.0294.5590 Comparative Example 7 Comparative Compound F 5.7695.49105 Comparative Example 8 Comparative Compound G 5.9992.18111 Comparative Example 9 Comparative Compound H 6.2089.3388 Comparative Example 10 Comparative Compound I 5.7990.1679 Comparative Example 11 Comparative Compound J5.8888.47106 Example 1 Compound 14.17120.45136 Example 2 Compound 164.31118.44138 Example 3 Compound 304.16123.94130 Example 4 Compound 384.22122.11128 Example 5 Compound 494.14114.53125 Example 6 Compound 594.09116.44132 Example 7 Compound 664.10117.32122 Example 8 Compound 754.13115.91135 Example 9 Compound 834.25120.05136 Example 10 Compound 914.05117.38134 Example 11 Compound 1034.01118.35138 Example 12 Compound 1204.12120.35133 Example 13 Compound 1213.99118.21131 Example 14 Compound 1473.96114.41143 Example 15 Compound 1563.95121.17142 Example 16 Compound 1644.07120.11146 Example 17 Compound 1794.17121.19148 Example 18 Compound 1814.01120.10145 Example 19 Compound 1903.94115.74142 Example 20 Compound 1954.03119.76142 Example 21 Compound 1964.11116.33145 Example 22 Compound 1984.06115.96146

[0353]

[0354] The comparative compounds used in Table 8 above are as follows.

[0355]

[0356] From the above experimental example 1, it was confirmed that the organic light-emitting devices of Examples 1 to 22, which used the compound according to the present application in forming the hole transport layer, had superior luminous efficiency and lifespan compared to the organic light-emitting devices of Comparative Examples 1 to 11, which did not use the compound according to the present application in forming the hole transport layer.

[0357] Specifically, in the case of comparative compounds A and J, when compared with the heterocyclic compound represented by the chemical formula 1 of the present invention, the carbazole parent nucleus ( ) is different in that a methyl group is substituted on the benzene ring where the B1 to B4 substituents are located. In the case of the methyl group, the electron donating ability is small, so the HOMO level is lowered, which reduces the hole transport ability of the organic light-emitting device. Therefore, the operating voltage of the organic light-emitting device is increased, the efficiency is reduced, and the lifespan is shortened.

[0358] In the case of comparative compound B, when compared to the heterocyclic compound represented by the chemical formula 1 of the present invention, the carbazole nucleus ( ) in which a phenyl group is substituted on the benzene ring where the B1 to B4 substituents are located. The phenyl group has greater steric hindrance than the alkyl group, so the hole mobility decreases and the driving voltage increases. In addition, the charge balance is not correct, so the efficiency decreases, and the lifespan of the organic light-emitting device decreases due to deterioration caused by electron accumulation.

[0359] In the case of comparative compounds C, D, E, F, G, H and I, when compared with the heterocyclic compound represented by the above chemical formula 1 of the present invention, the carbazole parent nucleus ( ) is different in that the alkyl group is '1-substituted' on the benzene ring where the B1 to B4 substituents are located, and when comparative compounds C, D, E, F, G, H and I are applied to an organic light-emitting device, the HOMO level becomes lower than when the heterocyclic compound represented by the chemical formula 1 according to the present invention is applied to the organic light-emitting device, thereby lowering the hole transport ability of the device, thereby increasing the driving voltage, decreasing the efficiency and shortening the lifespan.

[0360]

[0361] Experimental Example 2

[0362] 1) Fabrication of organic light-emitting devices

[0363] A glass substrate coated with a 1,500 Å thick ITO (Indium Tin Oxide) film was ultrasonically cleaned in distilled water. After the distilled water cleaning, it was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UVO for 5 minutes in a UV cleaner. Afterwards, the substrate was transferred to a plasma cleaner (PT), and plasma treated in a vacuum to increase the ITO work function and remove any residual film, and then transferred to a thermal evaporation equipment for organic deposition.

[0364] Then, the vacuum level inside the chamber is 10 -6 After evacuating to 10 torr, a current was applied to the cell to evaporate 2-TNATA and deposit a hole injection layer with a thickness of 600 Å on an ITO substrate. N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) was added to another cell in the vacuum deposition equipment, and a current was applied to the cell to evaporate it and deposit a hole transport layer with a thickness of 300 Å on the hole injection layer. Thereafter, the compounds listed in Table 9 below were deposited as a hole transport auxiliary layer with a thickness of 100 Å.

[0365]

[0366] On top of that, the emission layer was thermally vacuum deposited as follows. The emission layer was deposited with a thickness of 400 Å using 9-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-9'-phenyl-3,3'-bi-9H-carbazole as a host, and doped with [Ir(ppy)3] as a green phosphorescent dopant at 7% of the deposition thickness of the emission layer. Subsequently, bathocuproine (BCP) was deposited with a thickness of 60 Å as a hole-blocking layer, and Alq3 was deposited with a thickness of 200 Å as an electron-transporting layer thereon. Finally, lithium fluoride (LiF) was deposited on the electron transport layer to a thickness of 10 Å to form an electron injection layer, and then an aluminum (Al) cathode was deposited on the electron injection layer to a thickness of 1,200 Å to form a cathode, thereby manufacturing an organic light-emitting device.

[0367]

[0368] Meanwhile, all organic compounds required for manufacturing organic light-emitting devices are 10 for each material. -6 ~10 -8 It was purified by vacuum sublimation under 10 torr and used in the manufacture of organic light-emitting devices.

[0369]

[0370] 2) Driving voltage and luminous efficiency of organic electroluminescent devices

[0371] The electroluminescence (EL) characteristics of the organic light-emitting devices manufactured as described above were measured using M7000 from MaxScience, and the standard luminance was determined to be 6,000 cd / m using the lifespan measurement equipment (M6000) manufactured by MaxScience based on the measurement results. 2 The lifespan T is the time it takes for the initial luminance to reach 95% of its original brightness.95 (Unit: h, time) was measured. The results of measuring the driving voltage, luminous efficiency, and lifespan of the organic light-emitting device of the present invention as shown in the above measurement results are as shown in Table 9 below.

[0372] Compound Driving Voltage (V) Efficiency (cd / A) Lifespan (T) 95 ) Comparative Example 12 Comparative Compound A 5.796.543 Comparative Example 13 Comparative Compound B 6.066.842 Comparative Example 14 Comparative Compound C 5.796.444 Comparative Example 15 Comparative Compound D 5.765.932 Comparative Example 16 Comparative Compound E 5.964.843 Comparative Example 17 Comparative Compound F 6.865.142 Comparative Example 18 Comparative Compound G 5.956.044 Comparative Example 19 Comparative Compound H 5.904.332 Comparative Example 20 Comparative Compound I 5.996.643 Comparative Example 21 Comparative Compound J 6.746.242 Example 23 Compound 15.337.555 Example 24 Compound 165.328.254 Example 25 Compound 305.248.057 Example 26 Compound 385.377.953 Example 27 Compound 495.507.456 Example 28 Compound 595.467.358 Example 29 Compound 665.617.859 Example 30 Compound 755.577.754 Example 31 Compound 835.307.957 Example 32 Compound 915.278.058 Example 33 Compound 1035.358.159 Example 34 Compound 1205.417.656 Example 35 Compound 1215.287.855 Example 36 Compound 1475.317.661 Example 37 Compound 1565.347.862 Example 38 Compound 1645.268.063 Example 39 Compound 1795.397.561 Example 40 Compound 1815.407.662 Example 41 Compound 1905.227.963 Example 42 Compound 1955.247.961 Example 43 Compound 1965.308.260 Example 44 Compound 1985.297.863

[0373] The comparative compounds used in Table 9 above are as follows.

[0374]

[0375] From the above Experimental Example 2, it was confirmed that the organic light-emitting devices of Examples 23 to 44, which used the compound according to the present invention when forming the hole transport auxiliary layer, had lower driving voltages and better luminous efficiency and lifespans than the organic light-emitting devices of Comparative Examples 12 to 21, which did not use the compound according to the present invention when forming the hole transport auxiliary layer.

[0376] This means that when the compound according to the present application is used as a hole-assisting layer, the hole-assisting layer can more effectively perform the role of preventing electrons from the light-emitting layer from passing to the hole-transporting layer, like an electron-blocking layer, than when the compound according to the present application is not used, and additionally, the energy level and light-emitting wavelength between the light-emitting layer and the hole-transporting layer can be more effectively adjusted, thereby improving color purity.

[0377] This is because the degree of electron blocking and the tuning of the energy level and emission wavelength between the light-emitting layer and the hole transport layer are affected by the interaction of materials during deposition, and as described above, it is believed that this effect is caused by the difference in substituents and substitution positions between the compound of the present application and the comparative compound.

[0378]

[0379] [Explanation of symbols]

[0380] 100: Substrate

[0381] 200: Bipolar

[0382] 300: Organic layer

[0383] 301: Hole injection layer

[0384] 302: Hole transport layer

[0385] 303: Emissive layer

[0386] 304: Hole blocking layer

[0387] 305: Electron transport layer

[0388] 306: Electron injection layer

[0389] 400: Cathode

Claims

1. A heterocyclic compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, A1 to A5 are the same as or different from each other, and each independently represent hydrogen; deuterium; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R101R102; -SiR101R102R103 and a group represented by the following chemical formula 2, or two or more adjacent groups are combined to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same as or different from each other, and each independently represent a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, At least one of the above A1 to A5 is a group represented by the following chemical formula 2, [Chemical Formula 2] B1 to B4 are the same as or different from each other, and each independently represent hydrogen; deuterium; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R101R102 and -SiR101R102R103, or two or more adjacent groups are combined to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same or different from each other and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, At least two of the above B1 to B4 are substituted or unsubstituted C1 to C60 alkyl groups, In the above chemical formula 2, L1 to L3 are the same or different and each independently represents a single bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, Ar1 and Ar2 are the same or different, and each independently represents a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, n1 to n3 are equal to or different from each other and are each independently an integer from 0 to 3, If n1 is 2 or greater, L1 is equal or different, If n2 is 2 or greater, L2 is equal or different, If n3 is 2 or greater, L3 is equal to or different from each other, n4 and n5 are equal to or different from each other, and are each independently an integer from 1 to 5, If n4 is 2 or greater, Ar1 is equal or different, If n5 is 2 or greater, Ar2 is equal or different.

2. In paragraph 1, The above chemical formula 1 is represented by either the following chemical formula 1-1 or chemical formula 1-2. Heterocyclic compounds: [Chemical Formula 1-1] [Chemical Formula 1-2] In the above chemical formula 1-1, A1 to A4 are the same as or different from each other, and each independently represent hydrogen; deuterium; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R101R102; -SiR101R102R103 and a group represented by the above chemical formula 2, or two or more adjacent groups are combined to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same as or different from each other and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, At least one of the above A1 to A4 is a group represented by the above chemical formula 2, L4 is a single bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, Ar3 is a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, n6 is an integer from 0 to 3, and if it is 2 or greater, L4 is equal or different, n7 is an integer from 1 to 5, and if it is 2 or greater, Ar3 is the same or different, The definitions of B1 to B4 are the same as those in Chemical Formula 1, In the above chemical formula 1-2, A1 to A4 are the same as or different from each other, and each independently represent hydrogen; deuterium; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R101R102 and -SiR101R102R103, or two or more adjacent groups are combined to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same or different and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, The definitions of B1 to B4 are the same as those in Chemical Formula 1, The definitions of L1 to L3, Ar1, Ar2, n1 to n5 are the same as those in chemical formula 2.

3. In paragraph 2, The above Ar1 to Ar3 are represented by either the following chemical formula 3 or chemical formula 4, Heterocyclic compounds: [Chemical Formula 3] [Chemical Formula 4] In the above chemical formulas 3 and 4, X1 is O, S or CRaRb, Ar4 is a substituted or unsubstituted C6 to C60 aryl group, R1, R2, Ra and Rb are the same as or different from each other, and each independently represent hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R101R102 and -SiR101R102R103, or two or more adjacent groups are combined to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same or different and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, n8 is an integer from 0 to 4, and if it is 2 or greater, R1 is equal or different, n9 is an integer from 0 to 3, and if it is 2 or greater, R2 is equal or different.

4. In paragraph 1, B1 to B4 in the above chemical formula 1 are the same as or different from each other, and each independently represents hydrogen; deuterium; or a substituted or unsubstituted C3 to C10 alkyl group, wherein at least two of the B1 to B4 are substituted or unsubstituted C3 to C10 alkyl groups. Heterocyclic compounds.

5. In paragraph 1, A heterocyclic compound represented by the above chemical formula 1, which does not contain deuterium as a substituent or has a deuterium content of 1% to 100% based on the total number of hydrogen atoms and deuterium atoms.

6. In paragraph 1, The heterocyclic compound represented by the above chemical formula 1 is a heterocyclic compound represented by any one of the following compounds: .

7. First electrode; A second electrode provided opposite to the first electrode; and One or more organic layers provided between the first electrode and the second electrode; As an organic light-emitting device comprising: An organic light-emitting device, wherein the organic layer comprises at least one heterocyclic compound according to any one of claims 1 to 6.

8. In paragraph 7, The above organic layer includes a hole transport layer, An organic light-emitting device wherein the hole transport layer comprises the heterocyclic compound.

9. In paragraph 7, The above organic layer includes a hole transport auxiliary layer, An organic light-emitting device wherein the hole transport auxiliary layer comprises the heterocyclic compound.

10. In paragraph 7, An organic light-emitting device, wherein the organic light-emitting device further comprises one or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron injection layer, an electron transport layer, a battery blocking layer, and a hole blocking layer.

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