Heterocyclic compound, and organic light-emitting device and composition for organic layer, each comprising same

Abstract

The present invention relates to a heterocyclic compound represented by chemical formula 1, and an organic light-emitting device and a composition for an organic layer, each comprising same.

Description

Heterocyclic compound, organic light-emitting device containing the same, and composition for organic layer

[0001] This application claims the benefit of priority to Korean Patent Application No. 10-2023-0163718, dated November 22, 2023, and all the contents of the document in that Korean Patent Application are incorporated herein by reference.

[0002] The present invention relates to a heterocyclic compound, an organic light-emitting device comprising the same, and a composition for an organic layer.

[0003]

[0004] 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.

[0005] 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.

[0006] 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.

[0007] To improve the performance, lifespan, or efficiency of organic light-emitting devices, the development of materials for organic thin films is continuously required.

[0008]

[0009] [Previous literature]

[0010] [Patent Document]

[0011] U.S. Patent No. 4,356,429

[0012]

[0013] The purpose of the present invention is to provide a heterocyclic compound, an organic light-emitting device including the same, and a composition for an organic layer.

[0014]

[0015] To achieve the above purpose,

[0016] The present invention provides a heterocyclic compound represented by the following chemical formula 1.

[0017] [Chemical Formula 1]

[0018]

[0019] In the above chemical formula 1,

[0020] The above X1 is N; or CRa,

[0021] The above X2 is N; or CRb,

[0022] The above X3 is N; or CRc,

[0023] At least two of the above X1 to X3 are N,

[0024] The above Y1 is O; S; or NRd,

[0025] The above R1 to R5 and Ra to Rd are the same as or different from each other, and each independently 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; -SiR101R102R103; And -NR101R102, 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,

[0026] The above a1 is an integer from 0 to 4, and when a1 is 2 or greater, R1 is equal to or different from each other,

[0027] The above a2 is an integer from 0 to 4, and when a2 is 2 or greater, R2 are equal to or different from each other,

[0028] The above a3 is an integer from 0 to 4, and when a3 is 2 or greater, R3 is equal to or different from each other,

[0029] The above a4 is an integer from 0 to 3, and when a4 is 2 or greater, R4 are equal to or different from each other,

[0030] The above a5 is an integer from 0 to 4, and when a5 is 2 or greater, R5 are equal to or different from each other,

[0031] The above Ar1 is a substituted or unsubstituted C6 to C60 aryl group,

[0032] The above L1 and L2 are the same as or different from each other, and each independently represents a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a C2 to C60 heteroarylene group,

[0033] The above a6 is an integer from 0 to 5, and when a6 is 2 or greater, L1 is equal to or different from each other,

[0034] The above a7 is an integer from 0 to 5, and when a7 is 2 or greater, L2 are equal to or different from each other,

[0035] The above L3 is a substituted or unsubstituted C6 to C60 arylene group; or a C2 to C60 heteroarylene group,

[0036] The above a8 is an integer from 1 to 5, and when a8 is 2 or greater, L3 is equal to or different from each other.

[0037]

[0038] In addition, the present invention provides an organic light-emitting device in which the organic material layer further includes a heterocyclic compound represented by the following chemical formula 2 or chemical formula 3.

[0039] [Chemical Formula 2]

[0040]

[0041] [Chemical Formula 3]

[0042]

[0043] In the above chemical formulas 2 and 3,

[0044] The above R31, R32, R41 and R42 are the same as or different from each other, and each independently 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)R201R202; -SiR201R202R203; And -NR201R202, 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 R201, R202 and R203 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,

[0045] The above d1 is an integer from 0 to 7, and when d1 is 2 or more, R31 are equal to or different from each other,

[0046] The above d2 is an integer from 0 to 7, and when d2 is 2 or greater, R32 are equal to or different from each other,

[0047] The above e1 is an integer from 0 to 6, and when e1 is 2 or more, R41 is equal to or different from each other,

[0048] The above e2 is an integer from 0 to 4, and when e2 is 2 or greater, R42 are equal to or different from each other,

[0049] The above Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently represents a cyano group; -SiR201R202R203; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, and the above R201, R202 and R203 are the same as or different from each other, and each independently represents 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,

[0050] The above L11, L12, L21 and L22 are the same as or different from each other, and each independently represents a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group,

[0051] The above d3 is an integer from 0 to 5, and when d3 is 2 or greater, L11 are equal to or different from each other,

[0052] The above d4 is an integer from 0 to 5, and when d4 is 2 or greater, L12 are equal to or different from each other,

[0053] The above e3 is an integer from 0 to 5, and when e3 is 2 or greater, L21 are equal to or different from each other,

[0054] The above e4 is an integer from 0 to 5, and when e4 is 2 or greater, L22 are equal to or different from each other.

[0055]

[0056] In addition, the present invention provides a composition for an organic layer comprising a heterocyclic compound represented by the above chemical formula 1 and a heterocyclic compound represented by the above chemical formula 2 or chemical formula 3.

[0057]

[0058] The compound described herein can be used as an organic layer material of an organic light-emitting device. The compound can serve as a hole injection layer material, a hole transport layer material, a light-emitting layer material, an electron transport layer material, an electron injection layer material, etc. in the organic light-emitting device. In particular, the compound can be used as a light-emitting layer material of an organic light-emitting device, and the compound can be used alone as a light-emitting material, or can be used as a host material or dopant material of the light-emitting layer.

[0059] Specifically, the compound may be used alone as a light-emitting material, or as a host material or dopant material in a light-emitting layer. When the heterocyclic compound represented by the above chemical formula 1 is used in an organic layer, the driving voltage of the organic light-emitting device can be lowered, the light-emitting efficiency can be improved, and the lifespan characteristics can be improved.

[0060]

[0061] 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.

[0062]

[0063] Hereinafter, the present invention will be described in more detail.

[0064]

[0065] 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.

[0066] In this specification, "substituted or unsubstituted" means deuterium; halogen; cyano group; straight or branched chain alkyl group having a carbon atom ... -SiRR'R"; -P(=O)RR'; 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 is substituted or unsubstituted with a substituent in which two or more substituents selected from the above-mentioned substituents are linked, wherein R, R' and R" are the same as or different from each other, and each independently represents 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.

[0067] In this specification, halogen may be fluorine; chlorine; bromine; or iodine.

[0068] 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 a methyl group; an ethyl group; an n-propyl group; an isopropyl group; an n-butyl group; an isobutyl group; a tert-butyl group; a sec-butyl group; a 1-methyl-butyl group; a 1-ethyl-butyl group; an n-pentyl group; an isopentyl group; a neopentyl group; a tert-pentyl group; an n-hexyl group; a 1-methylpentyl group; a 2-methylpentyl group; a 4-methyl-2-pentyl group; a 3,3-dimethylbutyl group; a 2-ethylbutyl group; a n-heptyl group; a 1-methylhexyl group; a cyclopentylmethyl group; a cyclohexylmethyl group; n-octyl group; tert-octyl group; 1-methylheptyl group; 2-ethylhexyl group; 2-propylpentyl group; n-nonyl group; 2,2-dimethylheptyl group; 1-ethyl-propyl group; 1,1-dimethyl-propyl group; isohexyl group; 4-methylhexyl group; 5-methylhexyl group, etc., but are not limited thereto.

[0069] In the present specification, an 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 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; 2,2-bis(diphenyl-1-yl)vinyl-1-yl group; stilbenyl group; styrenyl group, etc., but are not limited thereto.

[0070] 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.

[0071] 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.

[0072] 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; for example, 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, 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; 4-tert-butylcyclohexyl group; cycloheptyl group; cyclooctyl group, etc., but are not limited thereto.

[0073] 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; for example, 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.

[0074] 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; for example, 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 20 carbon atoms. Specific examples of the aryl group include a phenyl group; a biphenyl group; a triphenyl group; a naphthyl group; 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; Acenaphthylenyl group; benzofluorenyl group; spirobifluorenyl group; 2,3-dihydro-1H-indenyl group; and condensed ring groups thereof, but are not limited thereto.

[0075] In the present specification, the phosphine oxide group is represented by -P(=O)R101R102, where R101 and R102 are the same or different from each other, 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; a dinaphthylphosphine oxide group, and the like.

[0076] 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.

[0077] In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be combined with each other to form a ring.

[0078] When the above fluorenyl group is substituted, It can be, but is not limited to, the following.

[0079] 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.

[0080]

[0081] 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, for example, 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 dioxynyl 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.

[0082] 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 amine group include 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; Biphenyltriphenylenylamine groups, etc. are included, but are not limited thereto.

[0083] 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.

[0084] 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 that is sterically closest to the substituent; or another substituent substituted on the atom substituted by the substituent. For example, two substituents substituted at ortho positions in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring may be interpreted as "adjacent" to each other.

[0085] 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 ( 2Since H, Deuterium (D)) is an isotope of hydrogen, some hydrogen atoms may be deuterium.

[0086] 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%.

[0087] 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.”

[0088] 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. -2 It can be expressed as , and the element symbol is D or 2 It can also be written as H.

[0089] In one embodiment of the present invention, an isotope means an atom having the same atomic number (Z) but a different mass number (A). An isotope can also be interpreted as an element having the same number of protons but a different number of neutrons.

[0090] In one embodiment of the present invention, the meaning of the content T% of a specific substituent can be defined as T2 / T1Х100 = T%, where 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.

[0091] 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.

[0092]

[0093] Additionally, in one embodiment of the present invention, the term “phenyl group having a deuterium content of 0%” may mean a phenyl group that does not contain deuterium atoms, i.e., has 5 hydrogen atoms.

[0094] 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, a phenyl group; a biphenyl group; a terphenyl group; a triphenylenyl group; a naphthyl group; anthracenyl group; a phenalenyl group; a phenanthrenyl group; a fluorenyl group; a pyrenyl group; a chrysenyl group; a perylenyl group; an azulenyl group, and the like. All aromatic hydrocarbon ring compounds known in the art that satisfy the above carbon number are included.

[0095]

[0096] The present invention provides a heterocyclic compound represented by the following chemical formula 1.

[0097] [Chemical Formula 1]

[0098]

[0099] In the above chemical formula 1,

[0100] The above X1 is N; or CRa,

[0101] The above X2 is N; or CRb,

[0102] The above X3 is N; or CRc,

[0103] At least two of the above X1 to X3 are N,

[0104] The above Y1 is O; S; or NRd,

[0105] The above R1 to R5 and Ra to Rd are the same as or different from each other, and each independently 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; -SiR101R102R103; And -NR101R102, 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,

[0106] The above a1 is an integer from 0 to 4, and when a1 is 2 or greater, R1 is equal to or different from each other,

[0107] The above a2 is an integer from 0 to 4, and when a2 is 2 or greater, R2 are equal to or different from each other,

[0108] The above a3 is an integer from 0 to 4, and when a3 is 2 or greater, R3 is equal to or different from each other,

[0109] The above a4 is an integer from 0 to 3, and when a4 is 2 or greater, R4 are equal to or different from each other,

[0110] The above a5 is an integer from 0 to 4, and when a5 is 2 or greater, R5 are equal to or different from each other,

[0111] The above Ar1 is a substituted or unsubstituted C6 to C60 aryl group,

[0112] The above L1 and L2 are the same as or different from each other, and each independently represents a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a C2 to C60 heteroarylene group,

[0113] The above a6 is an integer from 0 to 5, and when a6 is 2 or greater, L1 is equal to or different from each other,

[0114] The above a7 is an integer from 0 to 5, and when a7 is 2 or greater, L2 are equal to or different from each other,

[0115] The above L3 is a substituted or unsubstituted C6 to C60 arylene group; or a C2 to C60 heteroarylene group,

[0116] The above a8 is an integer from 1 to 5, and when a8 is 2 or greater, L3 is equal to or different from each other.

[0117]

[0118] In one embodiment of the present invention, the heterocyclic compound represented by the chemical formula 1 may be represented by any one of the following chemical formulas 1-1 to 1-4.

[0119] [Chemical Formula 1-1]

[0120]

[0121] [Chemical Formula 1-2]

[0122]

[0123] [Chemical Formula 1-3]

[0124]

[0125] [Chemical Formula 1-4]

[0126]

[0127] In the above chemical formulas 1-1 to 1-4,

[0128] The above X1 to X3, Y1, R1 to R5, L1 to L3, Ar1 and a1 to a8 are the same as defined in the above chemical formula 1.

[0129]

[0130] In one embodiment of the present invention, all of X1 to X3 may be N.

[0131] In another embodiment of the present invention, X1 and X2 may be N, and X3 may be CRc.

[0132] In another embodiment of the present invention, X1 and X3 may be N, and X2 may be CRb.

[0133] In another embodiment of the present invention, X2 and X3 may be N, and X1 may be CRa.

[0134]

[0135] In one embodiment of the present invention, the heterocyclic compound represented by the chemical formula 1 may be represented by any one of the following chemical formulas 1-5 to 1-7.

[0136] [Chemical Formula 1-5]

[0137]

[0138] [Chemical Formula 1-6]

[0139]

[0140] [Chemical Formula 1-7]

[0141]

[0142] In the above chemical formulas 1-5 to 1-7,

[0143] The above R1 to R5, Ra, Rc, Y1, L1 to L3, Ar1 and a1 to a8 are the same as defined in the above chemical formula 1.

[0144]

[0145] In one embodiment of the present invention, Y1 may be O.

[0146] In another embodiment of the present invention, Y1 may be S.

[0147] In another embodiment of the present invention, Y1 may be NRd.

[0148]

[0149] In one embodiment of the present invention, R1 to R5 and Ra to Rd 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; -SiR101R102R103; Or -NR101R102, or two or more adjacent groups may combine with each other 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 may be the same as or different from each other, and may each independently be 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.

[0150] In another embodiment of the present invention, R1 to R5 and Ra to Rd are the same as or different from each other, and each independently 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; a substituted or unsubstituted C2 to C20 heteroaryl group; -P(=O)R101R102; -SiR101R102R103; Or -NR101R102, 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, wherein R101, R102 and R103 may be the same as or different from each other, and may each independently be a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0151] In another embodiment of the present invention, R1 to R5 and Ra to Rd are the same as or different from each other, and each independently represent hydrogen; deuterium; halogen; a cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or 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.

[0152] In another embodiment of the present invention, R1 to R5 are the same as or different from each other, and each independently represent hydrogen; deuterium; halogen; a cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or 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.

[0153] In another embodiment of the present invention, R1 to R5 are the same as or different from each other, and each independently represent hydrogen; deuterium; a substituted or unsubstituted C6 to C20 aryl group; or 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.

[0154] In another embodiment of the present invention, R1 and R2 are the same as or different from each other, and each independently represent hydrogen; deuterium; a substituted or unsubstituted C6 to C20 aryl group; or 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.

[0155] In another embodiment of the present invention, R1 and R2 are the same as or different from each other, and each independently represent hydrogen; deuterium; a substituted or unsubstituted phenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted triphenylenyl group; or a substituted or unsubstituted dibenzothiophenyl 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.

[0156] In another embodiment of the present invention, R3 may be hydrogen; deuterium; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0157] In another embodiment of the present invention, R3 may be hydrogen; deuterium; or a substituted or unsubstituted C6 to C20 aryl group.

[0158] In another embodiment of the present invention, R3 may be hydrogen; deuterium; or a substituted or unsubstituted phenyl group.

[0159] In another embodiment of the present invention, R4 may be hydrogen; deuterium; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0160] In another embodiment of the present invention, R4 may be hydrogen; deuterium; a substituted or unsubstituted phenyl group; a substituted or unsubstituted carbazolyl group; or a substituted or unsubstituted dibenzofuranyl group.

[0161] In another embodiment of the present invention, R5 may be hydrogen; deuterium; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group, or two or more adjacent groups may be 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.

[0162] In another embodiment of the present invention, R5 may be hydrogen; deuterium; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted carbazolyl group; or a substituted or unsubstituted dibenzofuranyl group, or two or more adjacent groups may be 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.

[0163] In another embodiment of the present invention, Ra to Rc may be the same as or different from each other, and may each independently be hydrogen; deuterium; a substituted or unsubstituted C6 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0164] In another embodiment of the present invention, Ra to Rc may be the same as or different from each other, and may each independently be hydrogen; deuterium; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0165] In another embodiment of the present invention, Ra to Rc may be the same as or different from each other, and may each independently be hydrogen or deuterium.

[0166] In another embodiment of the present invention, Rd may be a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0167] In another embodiment of the present invention, Rd may be a substituted or unsubstituted C6 to C20 aryl group.

[0168] In another embodiment of the present invention, Rd may be a substituted or unsubstituted phenyl group; or a substituted or unsubstituted biphenyl group.

[0169]

[0170] In one embodiment of the present invention, Ar1 may be a substituted or unsubstituted C6 to C40 aryl group.

[0171] In another embodiment of the present invention, Ar1 may be a substituted or unsubstituted C6 to C30 aryl group.

[0172] In another embodiment of the present invention, Ar1 may be a substituted or unsubstituted C6 to C20 aryl group.

[0173] In another embodiment of the present invention, Ar1 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 triphenylenyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted benzofluorenyl group; a substituted or unsubstituted spirobifluorenyl group; a substituted or unsubstituted spirofluorenebenzofluorenyl group; or a substituted or unsubstituted spirofluorenedibenzofluorenyl group.

[0174]

[0175] In one embodiment of the present invention, L1 and L2 may be the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted C6 to C30 arylene group; or a C2 to C30 heteroarylene group.

[0176] In another embodiment of the present invention, L1 and L2 may be the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted C6 to C20 arylene group; or a C2 to C20 heteroarylene group.

[0177] In another embodiment of the present invention, L1 and L2 are the same as or different from each other, and each independently may be a direct bond; a substituted or unsubstituted C6 to C20 arylene group.

[0178] In another embodiment of the present invention, L1 may be a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted biphenylene group.

[0179] In another embodiment of the present invention, L2 may be a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted naphthylene group; a substituted or unsubstituted triphenylene group; or a substituted or unsubstituted phenanthrene group.

[0180]

[0181] In one embodiment of the present invention, L3 may be a substituted or unsubstituted C6 to C30 arylene group; or a C2 to C30 heteroarylene group.

[0182] In another embodiment of the present invention, L3 may be a substituted or unsubstituted C6 to C20 arylene group; or a C2 to C20 heteroarylene group.

[0183] In another embodiment of the present invention, L3 may be a substituted or unsubstituted C6 to C20 arylene group.

[0184] In another embodiment of the present invention, L3 may be a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; or a substituted or unsubstituted terphenylene group.

[0185]

[0186] In one embodiment of the present invention, the above It may be represented by any one of the following chemical formulas A-1 to A-3.

[0187] [Chemical Formula A-1]

[0188]

[0189] [Chemical Formula A-2]

[0190]

[0191] [Chemical Formula A-3]

[0192]

[0193] In the above chemical formulas A-1 to A-3,

[0194] The above Y11 is O; or S,

[0195] The above R11 to R15 and Re 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; -SiR101R102R103; And -NR101R102, wherein R101, R102 and R103 are the same as or different from each other, and each independently represents 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,

[0196] The above b1 is an integer from 0 to 8, and when b1 is 2 or more, R11 are equal to or different from each other,

[0197] The above b2 is an integer from 0 to 4, and when b2 is 2 or greater, R12 are equal to or different from each other,

[0198] The above b3 is an integer from 0 to 6, and when b3 is 2 or greater, R13 is equal to or different from each other,

[0199] The above b4 is an integer from 0 to 4, and when b4 is 2 or greater, R14 are equal to or different from each other,

[0200] The above b5 is an integer from 0 to 6, and when b5 is 2 or greater, R15 is equal to or different from each other,

[0201] The above L1 and a6 are identical to the definitions in the above chemical formula 1.

[0202]

[0203] In one embodiment of the present invention, Y11 may be O.

[0204] In another embodiment of the present invention, Y11 may be S.

[0205]

[0206] In one embodiment of the present invention, R11 to R15 and Re 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; -SiR101R102R103; Or -NR101R102, wherein R101, R102 and R103 are the same as or different from each other, and each independently may be 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.

[0207] In another embodiment of the present invention, R11 to R15 and Re 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; a substituted or unsubstituted C2 to C20 heteroaryl group; -P(=O)R101R102; -SiR101R102R103; Or -NR101R102, wherein R101, R102 and R103 are the same as or different from each other, and each independently may be a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0208] In another embodiment of the present invention, R11 to R15 and Re may be the same as or different from each other, and may each independently be hydrogen; deuterium; halogen; a cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0209] In another embodiment of the present invention, R11 to R15 and Re may be the same as or different from each other, and may each independently be hydrogen; deuterium; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0210] In another embodiment of the present invention, R11 to R15 are the same as or different from each other, and may each independently be hydrogen or deuterium.

[0211] In another embodiment of the present invention, Re may be a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0212] In another embodiment of the present invention, Re may be a substituted or unsubstituted C6 to C20 aryl group.

[0213] In another embodiment of the present invention, Re may be a substituted or unsubstituted phenyl group; or a substituted or unsubstituted biphenyl group.

[0214]

[0215] In one embodiment of the present invention, the above It may be represented by any one of the following chemical formulas B-1 to B-3.

[0216] [Chemical Formula B-1]

[0217]

[0218] [Chemical Formula B-2]

[0219]

[0220] [Chemical Formula B-3]

[0221]

[0222] In the above chemical formulas B-1 to B-3,

[0223] The above Y21 is O; or NRf,

[0224] The above R21 to R23 and Rf are the same as or different from each other, and each independently 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; -SiR101R102R103; And -NR101R102, wherein R101, R102 and R103 are the same as or different from each other, and each independently represents 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,

[0225] The above c1 is an integer from 0 to 4, and when c1 is 2 or more, R21 are equal to or different from each other,

[0226] The above c2 is an integer from 0 to 6, and when c2 is 2 or more, R22 are equal to or different from each other,

[0227] The above c3 is an integer from 0 to 6, and when c3 is 2 or more, R23 are equal to or different from each other,

[0228] The definitions of Y1, R4, L3, a4 and a8 above are the same as in Chemical Formula 1.

[0229]

[0230] In one embodiment of the present invention, Y1 may be S and Y21 may be NRf.

[0231] In another embodiment of the present invention, Y1 may be NRd and Y21 may be O.

[0232]

[0233] In one embodiment of the present invention, R21 to R23 and Rf 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; -SiR101R102R103; Or -NR101R102, wherein R101, R102 and R103 are the same as or different from each other, and each independently may be 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.

[0234] In another embodiment of the present invention, R21 to R23 and Rf are the same as or different from each other, and each independently 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; a substituted or unsubstituted C2 to C20 heteroaryl group; -P(=O)R101R102; -SiR101R102R103; Or -NR101R102, wherein R101, R102 and R103 are the same as or different from each other, and each independently may be a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0235] In another embodiment of the present invention, R21 to R23 and Rf may be the same as or different from each other, and each independently be hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0236] In another embodiment of the present invention, R21 to R23 and Rf may be the same as or different from each other, and may each independently be hydrogen; deuterium; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0237] In another embodiment of the present invention, R21 to R23 are the same as or different from each other, and may each independently be hydrogen or deuterium.

[0238] In another embodiment of the present invention, Rf may be a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0239] In another embodiment of the present invention, Rf may be a substituted or unsubstituted C6 to C20 aryl group.

[0240] In another embodiment of the present invention, Rf may be a substituted or unsubstituted phenyl group.

[0241]

[0242] In one embodiment of the present invention, all of R1 to R5, Ra to Rf, R11 to R15, R21 to R23, Ar1, and L1 to L3 may include non-deuterated hydrogen (H).

[0243] In another embodiment of the present invention, at least one of R1 to R5, Ra to Rf, R11 to R15, R21 to R23, Ar1 and L1 to L3 may contain deuterium (D), and at least one of R1 to R5, Ra to Rf, R11 to R15, R21 to R23, Ar1 and L1 to L3 may contain non-deuterated hydrogen.

[0244] In another embodiment of the present invention, R1 to R5, Ra to Rf, R11 to R15, R21 to R23, Ar1 and L1 to L3 may all contain deuterium.

[0245]

[0246] In one embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 1 may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be, for example, more than 0%, 1% or more, 10% or more, 20% or more, 30% or more, 40% or more, or 50% or more, and may be 100% or less, 90% or less, 80% or less, 70% or less, or 60% or less.

[0247] In another embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 1 may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 1% to 100%.

[0248] In another embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 1 may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 20% to 90%.

[0249] In another embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 1 may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 30% to 80%.

[0250] In another embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 1 may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 50% to 70%.

[0251]

[0252] In one embodiment of the present invention, the heterocyclic compound represented by the chemical formula 1 may be represented by any one of the following compounds.

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266] In addition, by introducing various substituents into the structure of the above chemical formula 1, compounds having unique characteristics of the introduced substituents can be synthesized. For example, by introducing substituents mainly used in hole injection layer materials, hole transport layer materials, light-emitting layer materials, electron transport layer materials, electron blocking layer materials, and charge generation layer materials used in the manufacture of organic light-emitting devices into the core structure, a material satisfying the conditions required for each organic layer can be synthesized.

[0267] 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.

[0268] Meanwhile, the heterocyclic compound exhibits excellent thermal stability due to its high glass transition temperature (Tg). This increased thermal stability is an important factor in providing operating stability to the device.

[0269] The heterocyclic compound according to one embodiment of the present invention can be prepared through a multi-step chemical reaction. Some intermediate compounds are prepared first, and then the compound of formula 1 can be prepared from these intermediate compounds. More specifically, the heterocyclic compound according to one embodiment of the present invention can be prepared based on the preparation example described below.

[0270]

[0271] 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”.

[0272]

[0273] In addition, the present invention

[0274] First electrode;

[0275] A second electrode provided opposite to the first electrode; and

[0276] An organic light-emitting device comprising at least one organic layer provided between the first electrode and the second electrode,

[0277] The present invention relates to an organic light-emitting device, wherein at least one of the organic layers comprises a heterocyclic compound represented by the chemical formula 1.

[0278]

[0279] In one embodiment of the present invention, the first electrode may be an anode, and the second electrode may be a cathode.

[0280] In another embodiment, the first electrode may be a cathode and the second electrode may be an anode.

[0281]

[0282] In one embodiment of the present invention, 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 material.

[0283] In another embodiment of the present invention, the organic light-emitting device may be a blue organic light-emitting device, and the heterocyclic compound represented by the chemical formula 1 may be used as a material for the blue organic light-emitting material.

[0284] In another embodiment of the present invention, 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 material.

[0285]

[0286] In one embodiment of the present invention, 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 light-emitting layer material of the red organic light-emitting device.

[0287] In another embodiment of the present invention, the organic light-emitting device may be a blue organic light-emitting device, and the heterocyclic compound represented by the chemical formula 1 may be used as a light-emitting layer material of the blue organic light-emitting device.

[0288] In another embodiment of the present invention, 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 light-emitting layer material of the green organic light-emitting device.

[0289]

[0290] The specific details of the heterocyclic compound represented by the above chemical formula 1 are the same as described above.

[0291]

[0292] The organic light-emitting device of the present invention can be manufactured using a conventional method and material for manufacturing an organic light-emitting device, except that one or more organic layers are formed using the above-described heterocyclic compound.

[0293] 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.

[0294] 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 multilayer 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, an electron blocking layer, a hole transport layer, a light-emitting layer, an electron transport layer, a hole blocking 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.

[0295]

[0296] In the organic light-emitting device of the present invention, the organic layer includes a light-emitting layer, and the light-emitting layer may include a heterocyclic compound represented by the chemical formula 1. When the heterocyclic compound is used in the light-emitting layer, the HOMO (Highest Occupied Molecular Orbital) and the LUMO (Lowest Unoccupied Molecular Orbital) are spatially separated, thereby enabling strong charge transfer, and thus the operating efficiency and lifespan of the organic light-emitting device may be improved.

[0297]

[0298] In an organic light-emitting device according to one embodiment of the present invention, an organic material layer including a heterocyclic compound represented by the chemical formula 1 is provided, wherein the organic light-emitting device further includes a heterocyclic compound represented by the chemical formula 2 or 3.

[0299] [Chemical Formula 2]

[0300]

[0301] [Chemical Formula 3]

[0302]

[0303] In the above chemical formulas 2 and 3,

[0304] The above R31, R32, R41 and R42 are the same as or different from each other, and each independently 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)R201R202; -SiR201R202R203; And -NR201R202, 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 R201, R202 and R203 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,

[0305] The above d1 is an integer from 0 to 7, and when d1 is 2 or more, R31 are equal to or different from each other,

[0306] The above d2 is an integer from 0 to 7, and when d2 is 2 or greater, R32 are equal to or different from each other,

[0307] The above e1 is an integer from 0 to 6, and when e1 is 2 or more, R41 is equal to or different from each other,

[0308] The above e2 is an integer from 0 to 4, and when e2 is 2 or greater, R42 are equal to or different from each other,

[0309] The above Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and each independently represents a cyano group; -SiR201R202R203; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, and the above R201, R202 and R203 are the same as or different from each other, and each independently represents 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,

[0310] The above L11, L12, L21 and L22 are the same as or different from each other, and each independently represents a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group,

[0311] The above d3 is an integer from 0 to 5, and when d3 is 2 or greater, L11 are equal to or different from each other,

[0312] The above d4 is an integer from 0 to 5, and when d4 is 2 or greater, L12 are equal to or different from each other,

[0313] The above e3 is an integer from 0 to 5, and when e3 is 2 or greater, L21 are equal to or different from each other,

[0314] The above e4 is an integer from 0 to 5, and when e4 is 2 or greater, L22 are equal to or different from each other.

[0315]

[0316] In one embodiment of the present invention, R31, R32, R41 and R42 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)R201R202; -SiR201R202R203; Or -NR201R202, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C30 heterocycle, wherein R201, R202 and R203 are the same as or different from each other, and each independently may be 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.

[0317] In another embodiment of the present invention, R31, R32, R41 and R42 are the same as or different from each other, and each independently 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; a substituted or unsubstituted C2 to C20 heteroaryl group; -P(=O)R201R202; -SiR201R202R203; Or -NR201R202, or two or more adjacent groups are 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 R201, R202 and R203 are the same as or different from each other, and each independently may be a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0318] In another embodiment of the present invention, R31, R32, R41 and R42 may be the same as or different from each other, and each independently be 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; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0319] In another embodiment of the present invention, R31, R32, R41 and R42 may be the same as or different from each other, and may each independently be hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0320] In another embodiment of the present invention, R31, R32, R41 and R42 are the same as or different from each other, and may each independently be hydrogen or deuterium.

[0321]

[0322] In one embodiment of the present invention, Ar11, Ar12, Ar21 and Ar22 may be the same as or different from each other, and may each independently be a cyano group; a substituted or unsubstituted C6 to C30 aryl group; a substituted or unsubstituted C2 to C30 heteroaryl group; or -SiR201R202R203, and R201, R202 and R203 may be the same as or different from each other, and may each independently be 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.

[0323] In another embodiment of the present invention, Ar11, Ar12, Ar21 and Ar22 may be the same as or different from each other, and may each independently be a cyano group; a substituted or unsubstituted C6 to C20 aryl group; a substituted or unsubstituted C2 to C20 heteroaryl group; or -SiR201R202R203, and R201, R202 and R203 may be the same as or different from each other, and may each independently be a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0324] In another embodiment of the present invention, Ar11 and Ar12 may be the same as or different from each other, and each independently represent a cyano group; 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 triphenylenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted spirobifluorenyl group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted dibenzothiophenyl group; or SiR201R202R203, and R201, R202, and R203 may be substituted or unsubstituted phenyl groups.

[0325] In another embodiment of the present invention, Ar21 and Ar22 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 terphenyl group; a substituted or unsubstituted triphenylenyl group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group.

[0326]

[0327] In one embodiment of the present invention, L11, L12, L21 and L22 may be the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted C6 to C30 arylene group; or a substituted or unsubstituted C2 to C30 heteroarylene group.

[0328] In another embodiment of the present invention, L11, L12, L21 and L22 may be the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted C6 to C20 arylene group; or a substituted or unsubstituted C2 to C20 heteroarylene group.

[0329] In another embodiment of the present invention, L11 and L12 are the same as or different from each other, and each independently may be a direct bond; a substituted or unsubstituted C6 to C20 arylene group.

[0330] In another embodiment of the present invention, L11 and L12 may be the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted biphenylene group.

[0331] In another embodiment of the present invention, L21 and L22 may be the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted C6 to C20 arylene group; or a substituted or unsubstituted C2 to C20 heteroarylene group.

[0332] In another embodiment of the present invention, L21 and L22 may be the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; or a substituted or unsubstituted dibenzofuranylene group.

[0333]

[0334] In one embodiment of the present invention, all of R31, R32, R41, R42, Ar11, Ar12, Ar21, Ar22, L11, L12, L21 and L22 may include non-deuterated hydrogen (H).

[0335] In another embodiment of the present invention, at least one of R31, R32, R41, R42, Ar11, Ar12, Ar21, Ar22, L11, L12, L21 and L22 comprises deuterium (D), and at least one of R31, R32, R41, R42, Ar11, Ar12, Ar21, Ar22, L11, L12, L21 and L22 may comprise non-deuterated hydrogen.

[0336] In another embodiment of the present invention, R31, R32, R41, R42, Ar11, Ar12, Ar21, Ar22, L11, L12, L21 and L22 may all contain deuterium.

[0337]

[0338] In one embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 2 or the heterocyclic compound represented by the above chemical formula 3 may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be, for example, more than 0%, 1% or more, 10% or more, 20% or more, 30% or more, 40% or more, or 50% or more, and may be 100% or less, 90% or less, 80% or less, 70% or less, or 60% or less.

[0339] In another embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 2 or the heterocyclic compound represented by the above chemical formula 3 may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 1% to 100%.

[0340] In another embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 2 or the heterocyclic compound represented by the above chemical formula 3 may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 20% to 90%.

[0341] In another embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 2 or the heterocyclic compound represented by the above chemical formula 3 may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 30% to 80%.

[0342] In another embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 2 or the heterocyclic compound represented by the above chemical formula 3 may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 50% to 70%.

[0343]

[0344] In one embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 2 may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be, for example, more than 0%, 1% or more, 10% or more, 20% or more, 30% or more, 40% or more, or 50% or more, and may be 100% or less, 90% or less, 80% or less, 70% or less, or 60% or less.

[0345] In another embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 2 may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 1% to 100%.

[0346] In another embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 2 may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 20% to 90%.

[0347] In another embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 2 may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 30% to 80%.

[0348] In another embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 2 may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 50% to 70%.

[0349]

[0350] In one embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 3 may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be, for example, more than 0%, 1% or more, 10% or more, 20% or more, 30% or more, 40% or more, or 50% or more, and may be 100% or less, 90% or less, 80% or less, 70% or less, or 60% or less.

[0351] In another embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 3 may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 1% to 100%.

[0352] In another embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 3 may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 20% to 90%.

[0353] In another embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 3 may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 30% to 80%.

[0354] In another embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 3 may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 50% to 70%.

[0355]

[0356] When the heterocyclic compound represented by the above chemical formula 1 and the heterocyclic compound represented by the above chemical formula 2, or the heterocyclic compound represented by the above chemical formula 1 and the heterocyclic compound represented by the above chemical formula 3 are simultaneously included, better efficiency and lifespan effects are exhibited. From this, it can be expected that an exciplex phenomenon will occur when the two compounds are simultaneously included.

[0357] The above exciplex phenomenon is a phenomenon in which energy of the size of the HOMO energy level of the donor (p-host) and the LUMO energy level of the acceptor (n-host) is released due to electron exchange between two molecules. When the exciplex phenomenon between two molecules occurs, reverse intersystem crossing (RISC) occurs, and this can increase the internal quantum efficiency of fluorescence up to 100%. When a donor (p-host) with a good hole transport ability and an acceptor (n-host) with a good electron transport ability are used as the host of the light-emitting layer, holes are injected into the p-host and electrons are injected into the n-host, so the driving voltage can be lowered, which can help improve the lifespan. That is, when a heterocyclic compound represented by the above chemical formula 1 is used as the acceptor and a heterocyclic compound represented by the above chemical formula 2 or 3 is used as the donor, excellent device characteristics are exhibited.

[0358]

[0359] In one embodiment of the present invention, when the heterocyclic compound represented by the above chemical formula 1 and the heterocyclic compound represented by the above chemical formula 2 are simultaneously included, at least one of the compounds may not include deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be more than 0%, 1% or more, 10% or more, 20% or more, 30% or more, 40% or more, or 50% or more, and may be 100% or less, 90% or less, 80% or less, 70% or less, or 60% or less.

[0360] In another embodiment of the present invention, at least one of the compounds may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 1% to 100%.

[0361] In another embodiment of the present invention, at least one of the compounds may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 20% to 90%.

[0362] In another embodiment of the present invention, at least one of the compounds may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 30% to 80%.

[0363] In another embodiment of the present invention, at least one of the compounds may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 50% to 70%.

[0364]

[0365] In one embodiment of the present invention, when the heterocyclic compound represented by the above chemical formula 1 and the heterocyclic compound represented by the above chemical formula 3 are simultaneously included, at least one of the compounds may not include deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be more than 0%, 1% or more, 10% or more, 20% or more, 30% or more, 40% or more, or 50% or more, and may be 100% or less, 90% or less, 80% or less, 70% or less, or 60% or less.

[0366] In another embodiment of the present invention, at least one of the compounds may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 1% to 100%.

[0367] In another embodiment of the present invention, at least one of the compounds may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 20% to 90%.

[0368] In another embodiment of the present invention, at least one of the compounds may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 30% to 80%.

[0369] In another embodiment of the present invention, at least one of the compounds may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 50% to 70%.

[0370]

[0371] In one embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 2 may be represented by any one of the following compounds.

[0372]

[0373]

[0374]

[0375]

[0376]

[0377]

[0378]

[0379] In one embodiment of the present invention, the heterocyclic compound represented by the chemical formula 3 may be represented by any one of the following chemical formulas 3-1 to 3-6.

[0380] [Chemical Formula 3-1]

[0381]

[0382] [Chemical Formula 3-2]

[0383]

[0384] [Chemical Formula 3-3]

[0385]

[0386] [Chemical Formula 3-4]

[0387]

[0388] [Chemical Formula 3-5]

[0389]

[0390] [Chemical Formula 3-6]

[0391]

[0392] In the above chemical formulas 3-1 to 3-6,

[0393] The above R41, R42, Ar21, Ar22, L21, L22 and e1 to e4 are the same as defined in the above chemical formula 3.

[0394]

[0395] In one embodiment of the present invention, the heterocyclic compound represented by the chemical formula 3 may be represented by any one of the following compounds.

[0396]

[0397]

[0398]

[0399]

[0400]

[0401]

[0402]

[0403] In addition, in one embodiment of the present invention, a composition for an organic layer is provided, which comprises a heterocyclic compound represented by the above chemical formula 1, a heterocyclic compound represented by the above chemical formula 2, or a heterocyclic compound represented by the above chemical formula 3.

[0404] The specific details of the heterocyclic compound represented by the above chemical formula 1, the heterocyclic compound represented by the above chemical formula 2, and the heterocyclic compound represented by the above chemical formula 3 are the same as described above.

[0405]

[0406] In one embodiment of the present invention, the weight ratio of the heterocyclic compound represented by the chemical formula 1 and the heterocyclic compound represented by the chemical formula 2 or the heterocyclic compound represented by the chemical formula 3 in the composition for the organic layer may be 1:9 to 9:1, 1:9 to 5:5, or 2:8 to 5:5, but is not limited thereto.

[0407] In another embodiment of the present invention, the weight ratio of the heterocyclic compound represented by the chemical formula 1 and the heterocyclic compound represented by the chemical formula 2 in the composition for the organic layer may be 1:9 to 9:1, 1:9 to 5:5, or 2:8 to 5:5, but is not limited thereto.

[0408] In another embodiment of the present invention, the weight ratio of the heterocyclic compound represented by the chemical formula 1 and the heterocyclic compound represented by the chemical formula 3 in the composition for the organic layer may be 1:9 to 9:1, 1:9 to 5:5, or 2:8 to 5:5, but is not limited thereto.

[0409]

[0410] The above composition for an organic layer can be used when forming an organic material of an organic light-emitting device, and in particular, can be more preferably used when forming a host for a light-emitting layer.

[0411]

[0412] In one embodiment of the present invention, the organic layer includes a heterocyclic compound represented by the chemical formula 1 and a heterocyclic compound represented by the chemical formula 2, and can be used together with a phosphorescent dopant.

[0413] In another embodiment of the present invention, the organic layer includes a heterocyclic compound represented by the chemical formula 1 and a heterocyclic compound represented by the chemical formula 3, and can be used together with a phosphorescent dopant.

[0414]

[0415] As the above phosphorescent dopant material, those known in the art can be used. For example, phosphorescent dopant materials represented by LL'MX', LL'L"M, LMX'X", L2MX', and L3M can be used, but the scope of the present invention is not limited by these examples.

[0416] The above M can be iridium, platinum, osmium, etc.

[0417] The above L is sp 2 An anionic two-dentate ligand coordinated to M by carbon and heteroatoms, and X can perform the function of trapping electrons or holes. Non-limiting examples of L include 2-(1-naphthyl)benzoxazole, 2-phenylbenzoxazole, 2-phenylbenzothiazole, 7,8-benzoquinoline, phenylpyridine, benzothiophenylpyridine, 3-methoxy-2-phenylpyridine, thiophenylpyridine, tolylpyridine, etc. Non-limiting examples of X' and X" include acetylacetonate (acac), hexafluoroacetylacetonate, salicylidene, picolinate, 8-hydroxyquinolinate, etc.

[0418] Specific examples of the above phosphorescent dopants are shown below, but are not limited to these examples.

[0419]

[0420]

[0421] In one embodiment of the present invention, the organic layer includes a heterocyclic compound represented by the chemical formula 1 and a heterocyclic compound represented by the chemical formula 2, and can be used together with an iridium-based dopant.

[0422] In another embodiment of the present invention, the organic layer includes a heterocyclic compound represented by the chemical formula 1 and a heterocyclic compound represented by the chemical formula 3, and can be used together with an iridium-based dopant.

[0423]

[0424] In one embodiment of the present invention, the iridium-based dopant may be (piq)2(Ir)(acac) as a red phosphorescent dopant or Ir(ppy)3 as a green phosphorescent dopant.

[0425]

[0426] In one embodiment of the present invention, the content of the dopant may be 1% to 15%, preferably 2% to 10%, and more preferably 3% to 7% based on the total weight of the light-emitting layer.

[0427]

[0428] In an organic light-emitting device according to one embodiment of the present invention, the organic layer includes an electron injection layer or an electron transport layer, and the electron injection layer or the electron transport layer may include a heterocyclic compound represented by the chemical formula 1.

[0429] In an organic light-emitting device according to another embodiment of the present invention, the organic layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer may include a heterocyclic compound represented by the chemical formula 1.

[0430] In an organic light-emitting device according to another embodiment, the organic layer includes an electron transport layer, a light-emitting layer, or a hole blocking layer, and the electron transport layer, light-emitting layer, or hole blocking layer may include a heterocyclic compound represented by the chemical formula 1.

[0431] In an organic light-emitting device according to another embodiment, the organic layer includes a light-emitting layer, and the light-emitting layer may include a heterocyclic compound represented by the chemical formula 1.

[0432] In an organic light-emitting device according to another embodiment, the organic layer includes a light-emitting layer, and the light-emitting layer may include a heterocyclic compound represented by the chemical formula 1, a heterocyclic compound represented by the chemical formula 2, or a heterocyclic compound represented by the chemical formula 3.

[0433] In an organic light-emitting device according to another embodiment, the organic layer includes a light-emitting layer, the light-emitting layer includes a host material, and the host material may include a heterocyclic compound represented by the chemical formula 1.

[0434] In an organic light-emitting device according to another embodiment, the light-emitting layer may include two or more host materials, at least one of the host materials may include a heterocyclic compound represented by the chemical formula 1, and the other may include a heterocyclic compound represented by the chemical formula 2.

[0435] In an organic light-emitting device according to another embodiment, the light-emitting layer may include two or more host materials, at least one of the host materials may include a heterocyclic compound represented by the chemical formula 1, and the other may include a heterocyclic compound represented by the chemical formula 3.

[0436] In an organic light-emitting device according to another embodiment, the light-emitting layer may be used by pre-mixing two or more host materials, and at least one of the two or more host materials may include a heterocyclic compound represented by the chemical formula 1, and the other may include a heterocyclic compound represented by the chemical formula 2.

[0437] In an organic light-emitting device according to another embodiment, the light-emitting layer may be used by pre-mixing two or more host materials, and at least one of the two or more host materials may include a heterocyclic compound represented by the chemical formula 1, and the other may include a heterocyclic compound represented by the chemical formula 3.

[0438] The above pre-mixed means that the light-emitting layer is made by first mixing the materials and placing them in a single container before depositing two or more host materials on the organic layer.

[0439]

[0440] An organic light-emitting device according to one embodiment 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, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

[0441]

[0442] 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.

[0443] 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.

[0444] 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.

[0445]

[0446] In one embodiment of the present invention,

[0447] Steps to prepare the substrate;

[0448] A step of forming a first electrode on the substrate;

[0449] A step of forming one or more organic layers on the first electrode; and

[0450] A method for manufacturing an organic light-emitting device, comprising: forming a second electrode on the organic layer of one or more layers; wherein the step of forming the organic layer of one or more layers includes forming the organic layer of one or more layers using a composition for an organic layer according to one embodiment of the present invention.

[0451]

[0452] In one embodiment of the present invention, the step of forming the organic layer may be a step of pre-mixing the heterocyclic compound represented by the chemical formula 1 and the heterocyclic compound represented by the chemical formula 2, or the heterocyclic compound represented by the chemical formula 1 and the heterocyclic compound represented by the chemical formula 3, and forming the organic layer using a thermal vacuum deposition method.

[0453] The above pre-mixed means that the heterocyclic compound represented by the above chemical formula 1 and the heterocyclic compound represented by the above chemical formula 2, or the heterocyclic compound represented by the above chemical formula 1 and the heterocyclic compound represented by the above chemical formula 3 are mixed in one supply source before being deposited on the organic layer.

[0454] The pre-mixed material may be referred to as a composition for an organic layer according to one embodiment of the present application.

[0455] The organic layer including the heterocyclic compound represented by the above chemical formula 1 may additionally include other substances as needed.

[0456] The organic layer containing both the heterocyclic compound represented by the above chemical formula 1 and the heterocyclic compound represented by the above chemical formula 2 may additionally contain other substances as needed.

[0457] The organic layer containing both the heterocyclic compound represented by the above chemical formula 1 and the heterocyclic compound represented by the above chemical formula 3 may additionally contain other substances as needed.

[0458]

[0459] In the 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, the heterocyclic compound represented by the above chemical formula 2, or the heterocyclic compound represented by the above chemical formula 3 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.

[0460]

[0461] 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.

[0462]

[0463] 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.

[0464]

[0465] 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"-tris[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.

[0466]

[0467] 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.

[0468]

[0469] 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.

[0470]

[0471] For example, LiF is typically used as an electron injection layer material in the art, but the present application is not limited thereto.

[0472]

[0473] 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 pre-mixed and deposited and used as a single source. In addition, a fluorescent material can be used as the light-emitting layer material, but a phosphorescent material can also be used. 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.

[0474]

[0475] 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.

[0476]

[0477] An organic light-emitting device according to one embodiment of the present invention may be a front-emitting, back-emitting, or double-sided emitting device depending on the material used.

[0478]

[0479] 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., on a principle similar to that applied to organic light-emitting devices.

[0480]

[0481] 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.

[0482]

[0483] <Manufacturing Example>

[0484] Manufacturing Example 1. Preparation of Compound 1-1

[0485]

[0486]

[0487] Manufacturing Example 1-1. Preparation of Compound 1-1a

[0488] 2,6-Dichloro-6-phenyl-1,3,5-triazine 30.0 g (132.7 mmol), (2-(9H-carbazol-9-yl)phenyl)boronic acid 38.1 g (132.7 mmol), Pd2(PPh3) 47.7 g (6.6 mmol), Na2CO3 28.1 g (265.4 mmol), tetrahydrofuran (THF) 300 mL, and distilled water 90 mL were added and stirred under reflux for 6 hours.

[0489] After the reaction was completed, distilled water and dichloromethane were added at room temperature to extract the mixture, and the organic layer was dried over MgSO4, and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (n-hexane / dichloromethane = 4:1 (volume ratio)) to obtain 41.5 g (yield 72%) of compound 1-1-a.

[0490]

[0491] Manufacturing Example 1-2. Preparation of Compound 1-1

[0492] Compound 1-1-a 20.0 g (46.2 mmol), (4-(dibenzo[b,d]furan-4-yl)phenyl)boronic acid 13.3 g (46.2 mmol), Pd2(PPh3) 42.7 g (2.3 mmol), K2CO3 12.8 g (92.4 mmol), 1,4-dioxane 200 mL, and distilled water 60 mL were added and stirred under reflux for 6 hours.

[0493] After the reaction was completed, distilled water and dichloromethane were added at room temperature to extract the mixture, and the organic layer was dried over MgSO4, and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (n-hexane / dichloromethane = 3:1 (volume ratio)) to obtain 25.0 g (84% yield) of compound 1-1.

[0494]

[0495] Except that Compound A of Table 1 was used instead of Compound 2,6-dichloro-6-phenyl-1,3,5-triazine in the above Preparation Example 1, Compound B of Table 1 was used instead of (2-(9H-carbazol-9-yl)phenyl)boronic acid, and Compound C of Table 1 was used instead of (4-(dibenzo[b,d]furan-4-yl)phenyl)boronic acid, the target compound of Table 1 was synthesized in the same manner as in Preparation Example 1. The yield refers to the yield of the final reaction.

[0496]

[0497]

[0498]

[0499]

[0500]

[0501]

[0502]

[0503]

[0504] Manufacturing Example 2. Preparation of Compound 1-82

[0505]

[0506]

[0507] Manufacturing Example 2-1. Preparation of compound 1-82-a

[0508] 30.0 g (123.3 mmol) of 1-phenyl-9H-carbazole, 30.3 g (123.3 mmol) of (1-fluorodibenzo[b,d]thiophen-4-yl)boronic acid, 80.3 g (246.6 mmol) of Cs2CO3, and 300 mL of dimethylacetamide (DMA) were added and stirred under reflux for 16 hours.

[0509] After the reaction was completed, distilled water and ethyl acetate were added at room temperature to extract the product, the organic layer was dried over MgSO4, and the solvent was removed using a rotary evaporator. The reactant was recrystallized using ethyl acetate and methanol to obtain 51.5 g (yield 89%) of compound 1-82-a.

[0510]

[0511] Manufacturing Example 2-2. Preparation of compound 1-82-b

[0512] 2-([1,1'-biphenyl]-3-yl)-4,6-dichloro-1,3,5-triazine (20.0 g (66.2 mmol), (2-(9H-carbazol-9-yl)phenyl)boronic acid) (19.0 g (66.2 mmol), Pd(PPh3) (43.8 g (3.3 mmol), Na2CO3 (14.0 g (132.4 mmol), tetrahydrofuran (THF) (200 mL), and distilled water (60 mL) were added and stirred under reflux for 6 hours.

[0513] After the reaction was completed, distilled water and dichloromethane were added at room temperature to extract the mixture, and the organic layer was dried over MgSO4, and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (n-hexane / dichloromethane = 4:1 (volume ratio)) to obtain 25.3 g (yield 75%) of compound 1-82-b.

[0514]

[0515] Manufacturing Example 2-3. Preparation of Compound 1-82-c

[0516] Compound 1-82-b 22.0 g (43.2 mmol), (3-chlorophenyl)boronic acid 6.8 g (43.2 mmol), Pd(PPh3) 42.5 g (2.2 mmol), K2CO3 11.9 g (8.6 mmol), 1,4-dioxane 220 mL, and distilled water 66 mL were added and stirred under reflux for 6 hours.

[0517] After the reaction was completed, distilled water and dichloromethane were added at room temperature to extract the mixture, and the organic layer was dried over MgSO4, and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (n-hexane / dichloromethane = 3:1 (volume ratio)) to obtain 21.8 g (yield 86%) of compound 1-82-c.

[0518]

[0519] Manufacturing Example 2-4. Preparation of Compound 1-82

[0520] Compound 1-82-c 15.0 g (25.6 mmol), compound 1-82-a 12.0 g (25.6 mmol), Pd2(dba) 31.2 g (1.3 mmol), XPhos 2.4 g (5.2 mmol), K2CO3 7.1 g (51.2 mmol), 1,4-dioxane 120 mL, and distilled water 63 mL were added and stirred under reflux for 6 hours.

[0521] After the reaction was completed, distilled water and dichloromethane were added at room temperature to extract the mixture, and the organic layer was dried over MgSO4, and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (n-hexane / dichloromethane = 2:1 (volume ratio)) to obtain 18.3 g (yield 73%) of compound 1-82.

[0522]

[0523] The target compounds in Table 2 below were synthesized in the same manner as in Preparation Example 2, except that Compound D in Table 2 below was used instead of Compound 2-([1,1'-biphenyl]3-yl)-2,6-dichloro-1,3,5-triazine in Preparation Example 2, Compound E in Table 2 below was used instead of (3-chlorophenyl)boronic acid, and Compound F in Table 2 below was used instead of Compound 1-82-a. The yield refers to the yield of the final reaction.

[0524]

[0525]

[0526]

[0527]

[0528]

[0529] Manufacturing Example 3. Preparation of Compound 1-208

[0530]

[0531]

[0532] Manufacturing Example 3-1. Preparation of compound 1-208-a

[0533] 20.0 g (77.8 mmol) of 12H-benzofuro[2,3-a]carbazole, 16.8 g (77.8 mmol) of (3'-fluoro-[1,1'-biphenyl]-2-yl)boronic acid, 50.7 g (155.4 mmol) of Cs2CO3, and 200 mL of dimethylacetamide (DMA) were added and stirred under reflux for 16 hours.

[0534] After the reaction was completed, distilled water and ethyl acetate were added at room temperature to extract the product, the organic layer was dried over MgSO4, and the solvent was removed using a rotary evaporator. The reactant was recrystallized using ethyl acetate and methanol to obtain 32.0 g (yield 91%) of compound 1-208-a.

[0535]

[0536] Manufacturing Example 3-2. Preparation of Compound 1-208-b

[0537] Compound 1-208-a 20 g (44.1 mmol), 2,4-dichloro-6-(naphthalen-2-yl)-1,3,5-triazine 12.2 g (44.1 mmol), Pd(PPh3) 42.5 g (2.2 mmol), Na2CO3 9.4 g (88.2 mmol), tetrahydrofuran (THF) 200 mL, and distilled water 60 mL were added and stirred under reflux for 6 hours.

[0538] After the reaction was completed, distilled water and dichloromethane were added at room temperature to extract the mixture, and the organic layer was dried over MgSO4, and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (n-hexane / dichloromethane = 4:1 (volume ratio)) to obtain 21.0 g (yield 73%) of compound 1-208-b.

[0539]

[0540] Manufacturing Example 3-3. Preparation of compound 1-208-c

[0541] Compound 1-208-b 20.0 g (30.8 mmol), (3-chlorophenyl)boronic acid 4.8 g (30.8 mmol), Pd(PPh3) 41.8 g (1.5 mmol), K2CO3 8.5 g (61.6 mmol), 1,4-dioxane 200 mL, and distilled water 60 mL were added and stirred under reflux for 6 hours.

[0542] After the reaction was completed, distilled water and dichloromethane were added at room temperature to extract the mixture, and the organic layer was dried over MgSO4, and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (n-hexane / dichloromethane = 3:1 (volume ratio)) to obtain 19.4 g (87% yield) of compound 1-208-c.

[0543]

[0544] Manufacturing Example 3-4. Preparation of Compound 1-208

[0545] Compound 1-208-c 20.0 g (27.6 mmol), (9-phenyldibenzo[b,d]furan-2-yl)boronic acid 7.9 g (27.6 mmol), Pd2(dba) 31.3 g (1.4 mmol), XPhos 2.6 g (5.5 mmol), K2CO3 7.6 g (55.2 mmol), 1,4-dioxane 200 mL, and distilled water 60 mL were added and stirred under reflux for 6 hours.

[0546] After the reaction was completed, distilled water and dichloromethane were added at room temperature to extract the mixture, and the organic layer was dried over MgSO4, and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (n-hexane / dichloromethane = 2:1 (volume ratio)) to obtain 18.8 g (yield 73%) of compound 1-208.

[0547]

[0548] The target compounds in Table 3 were synthesized in the same manner as in Preparation Example 3, except that Compound G in Table 3 was used instead of Compound 1-208-a in Preparation Example 3, Compound H in Table 3 was used instead of (3-chlorophenyl)boronic acid, and Compound I in Table 3 was used instead of (9-phenyldibenzo[b,d]furan-2-yl)boronic acid. The yield refers to the yield of the final reaction.

[0549]

[0550]

[0551]

[0552]

[0553]

[0554] Manufacturing Example 4. Preparation of Compound 2-1

[0555]

[0556]

[0557] Manufacturing Example 4-1. Preparation of Compound 2-1-a

[0558] 10.0 g (49.6 mmol) of 3-bromo-9H-carbazole, 24.2 g (148.8 mmol) of bromobenzene, 32.3 g (2.5 mmol) of Pd2(dba), 32.4 mL (9.9 mmol) of P(t-Bu), 9.53 g (99.2 mmol) of NaO-t-Bu, and 100 mL of toluene were added and heated at 135°C for 15 hours.

[0559] After the reaction was completed, distilled water and dichloromethane were added for extraction, and the resultant was purified by column chromatography to obtain 14.0 g (yield 98%) of compound 2-1-a.

[0560]

[0561] Manufacturing Example 4-2. Preparation of Compound 2-1

[0562] Compound 2-1-a 14.0 g (43.4 mmol), (9-phenyl-9H-carbazol-3-yl)boronic acid 14.9 g (52.0 mmol), Pd(PPh3) 42.5 g (2.2 mmol), K2CO3 17.9 g (130.0 mmol), 140 mL of 1,4-dioxane and 35 mL of distilled water were added and stirred at 120°C for 4 hours.

[0563] After that, the temperature was lowered to room temperature, and the resulting solid was washed with distilled water and methanol to obtain 17.0 g (yield 80%) of compound 2-1.

[0564]

[0565] The target compound of Table 4 was synthesized in the same manner as in Manufacturing Example 4, except that compound a of Table 4 was used instead of bromobenzene in Manufacturing Example 4, and compound b of Table 4 was used instead of (9-phenyl-9H-carbazol-3-yl)boronic acid. The yield refers to the yield of the final reaction.

[0566]

[0567]

[0568]

[0569]

[0570]

[0571]

[0572] Manufacturing Example 5. Preparation of Compound 2-61

[0573]

[0574]

[0575] Manufacturing Example 5-1. Preparation of compound 2-61-a

[0576] 10.0 g (40.2 mmol) of 3-bromo-9H-carbazole, 1,000 mL of D6-benzene, and 170.0 g (1.1 mmol) of triflic acid (CF3SO3H) were added and stirred at 50°C.

[0577] After the reaction was completed, the mixture was neutralized with D2O, extracted with Na2CO3 aqueous solution and dichloromethane at room temperature, and the organic layer was dried with MgSO4 and the solvent was removed using a rotary evaporator.

[0578] The reaction product was purified by column chromatography (n-hexane / dichloromethane = 2:1 (volume ratio)) and recrystallized with methanol to obtain 10.0 g (yield 98%) of compound 2-61-a.

[0579]

[0580] Manufacturing Example 5-2. Preparation of Compound 2-61-b

[0581] Compound 2-61-a 10.0 g (39.5 mmol), bromobenzene 12.4 g (79.0 mmol), Pd2(dba) 31.8 g (2.0 mmol), P(t-Bu) 31.9 mL (7.9 mmol), NaO-t-Bu 11.4 g (118.5 mmol), and toluene 100 mL were added and heated at 135°C for 15 hours.

[0582] After the reaction was completed, distilled water and dichloromethane were added for extraction, and the resultant was purified by column chromatography to obtain 11.0 g (yield 84%) of compound 2-61-b.

[0583]

[0584] Manufacturing Example 5-3. Preparation of Compound 2-61-c

[0585] 10.0 g (47.3 mmol) of 9H-carbazol-3-ylboronic acid, 1,000 mL of benzene (D6-benzene), and 170.0 g (1.1 mmol) of triflic acid (CF3SO3H) were added and stirred at 50°C.

[0586] After the reaction was completed, the mixture was neutralized with D2O, extracted with Na2CO3 aqueous solution and dichloromethane at room temperature, and the organic layer was dried with MgSO4 and the solvent was removed using a rotary evaporator.

[0587] The reaction product was purified by column chromatography (n-hexane / dichloromethane = 2:1 (volume ratio)) and recrystallized with methanol to obtain 9.0 g (yield 87%) of compound 2-61-c.

[0588]

[0589] Manufacturing Example 5-4. Preparation of compound 2-61-d

[0590] Compound 2-61-c 9.0 g (41.3 mmol), bromobenzene 12.9 g (82.5 mmol), Pd2(dba) 31.9 g (2.1 mmol), P(t-Bu) 32 mL (8.3 mmol), and NaO-t-OBu 7.9 g (82.6 mmol) were added, and then 100 mL of toluene was added and heated at 135°C for 15 hours.

[0591] After the reaction was completed, distilled water and dichloromethane were added for extraction, and the resultant was purified by column chromatography to obtain 10.0 g (yield 82%) of compound 2-61-d.

[0592]

[0593] Manufacturing Example 5-5. Preparation of Compound 2-61

[0594] Compound 2-61-b 10.0 g (30.4 mmol), compound 2-61-d 17.9 g (60.8 mmol), Pd(PPh3) 41.4 g (1.5 mmol), and K2CO3 12.6 g (91.1 mmol) were added, and then added to 140 mL of 1,4-dioxane and 35 mL of distilled water, and stirred at 120°C for 4 hours.

[0595] After that, the temperature was lowered to room temperature, and the resulting solid was washed with distilled water and methanol to obtain 13.0 g (yield 85%) of compound 2-61.

[0596]

[0597] The target compound of Table 5 below was synthesized using the same method as in Manufacturing Example 5, except that Compound c of Table 5 below was used instead of bromobenzene in Manufacturing Example 5-2, and Compound d of Table 5 below was used instead of bromobenzene in Manufacturing Example 5-4. The yield refers to the yield of the final reaction.

[0598]

[0599]

[0600]

[0601]

[0602] Manufacturing Example 6. Preparation of Compound 2-82

[0603]

[0604] 10.0 g (15.7 mmol) of compound 2-82-a (compound 2-32), 1,000 mL of D6-benzene, and 170.0 g (1.1 mmol) of triflic acid (CF3SO3H) were added and stirred at 50°C.

[0605] After the reaction was completed, the mixture was neutralized with D2O, extracted with Na2CO3 aqueous solution and dichloromethane at room temperature, and the organic layer was dried with MgSO4 and the solvent was removed using a rotary evaporator.

[0606] The reaction product was purified by column chromatography (n-hexane / dichloromethane = 2:1 (volume ratio)) and recrystallized with methanol to obtain 10.0 g (yield 95%) of the target compound 2-82.

[0607]

[0608] Manufacturing Example 7. Preparation of Compound 3-1

[0609]

[0610]

[0611] Manufacturing Example 7-1. Preparation of compound 3-1-a

[0612] 10.0 g (39.0 mmol) of 5,8-dihydroindolo[2,3-c]carbazole, 6.1 g (39.0 mmol) of bromobenzene, 31.8 g (2.0 mmol) of Pd2(dba), 30.9 mL (3.9 mmol) of P(t-Bu), 7.5 g (78.0 mmol) of NaO-t-Bu, and 100 mL of toluene were added and heated at 135°C for 15 hours.

[0613] After the reaction was completed, distilled water and dichloromethane were added for extraction, and the resultant was purified by column chromatography to obtain 7.3 g (yield 56%) of compound 3-1-a.

[0614]

[0615] Manufacturing Example 7-2. Preparation of Compound 3-1

[0616] Compound 3-1-a 7.3 g (22.0 mmol), bromobenzene 3.8 g (24.2 mmol), Pd2(dba) 31.0 g (1.1 mmol), P(t-Bu) 30.5 mL (3.9 mmol), NaO-t-OBu 4.2 g (44.0 mmol), and toluene 70 mL were added and heated at 135°C for 15 hours.

[0617] After the reaction was completed, distilled water and dichloromethane were added for extraction, and the resultant was purified by column chromatography to obtain 8.3 g (yield 93%) of compound 3-1.

[0618]

[0619] The target compounds in Table 6 below were synthesized in the same manner as in Preparation Example 7, except that compound c in Table 6 below was used instead of 5,8-dihydroindolo[2,3-c]carbazole in Preparation Example 7, compound d in Table 6 below was used instead of bromobenzene in Preparation Example 7-1, and compound e in Table 6 below was used instead of bromobenzene in Preparation Example 7-1. The yield refers to the yield of the final reaction.

[0620]

[0621]

[0622]

[0623]

[0624]

[0625]

[0626] The results of the synthesis of the compounds described in Manufacturing Examples 1 to 7 and Tables 1 to 6 are shown in Tables 7 and 8 below.

[0627] Table 7 below 1 The values ​​are measured by H NMR (CDCl3, 400 MHz), and Table 8 below is measured by FD-mass spectrometry (FD-MS: Field desorption mass spectrometry).

[0628]

[0629] Compound number 1H NMR(CDCl3, 400MHz)1-1δ= 8.55 (1H, d), 8.36 (2H, d), 8.25~8.19 (4H, m), 8.08~7.92 (4H, m), 7.80 (1H, t), 7.52~7.18 (16H, m)1-2δ= 8.55 (1H, d), 8.36 (2H, m), 8.25~8.19 (4H, m), 7.98~7.92 (2H, m), 7.83~7.80 (2H, m), 7.69~7.63 (2H, m), 7.52~7.18 (14H, m)1-5δ= 8.55 (1H, d), 8.36 (2H, m), 8.25~8.19 (4H, m), 8.08~7.92 (4H, m), 7.80 (1H, t), 7.52~7.18 (16H, m)1-7δ= 8.55 (1H, d), 8.36~8.16 (7H, m), 8.06 (1H, d), 7.92 (1H, d), 7.80 (1H, t), 7.62~7.50 (11H, m), 7.40 (1H, d), 7.29~7.11 (9H, m)1-14δ= 8.55 (1H, d), 8.36~8.17 (9H, m), 7.98~7.92 (3H, m), 7.80 (1H, t), 7.62~7.50 (19H, m)1-16δ= 8.55 (1H, d), 8.36 (2H, d), 8.25~8.19 (4H, m), 7.92~7.71 (8H, m), 7.62~7.41 (16H, m), 7.25~7.11 (6H, m)1-18δ= 8.65 (1H, d), 8.55 (1H, d), 8.42~8.36 (3H, m), 8.25~8.19 (4H, m), 7.98~7.92 (2H, m), 7.80 (1H, t), 7.62~7.11 (23H, m),1-25δ= 8.55 (2H, m), 8.45~8.17 (7H, m), 7.94~7.75 (7H, m), 7.52~7.25 (16H, m)1-26δ= 8.55 (1H, d), 8.45~8.17 (5H, m), 8.02~7.92 (4H, m), 7.89~7.79 (3H, m), 7.63 (2H, m), 7.52~7.20 (16H, m)1-31δ= 8.55 (2H, m), 8.45 (1H, d), 8.32~8.19 (5H, m), 7.92~7.80 (5H, m), 7.65 (1H, d), 7.52~7.20 (16H, m)1-35δ= 8.55 (4H, m), 8.45 (1H, d), 8.32~8.19 (5H, m), 7.92~7.80 (5H, m), 7.52~7.20 (16H, m)1-39δ= 8.55 (1H, d), 8.25~8.19 (8H, m), 8.08~7.92 (4H, m), 7.80~7.75 (3H, m), 7.63 (2H, m), 7.54~7.11 (18H, m)1-47δ= 8.55 (2H, m), 8.45 (2H, d), 8.32~8.19 (5H, m), 7.92~7.80 (5H, m), 7.56~7.49 (8H, m), 7.32~7.20 (7H, m)1-53δ= 8.55 (1H, d), 8.38~8.39 (3H, m), 8.20 (2H, m), 8.08~7.92 (4H, m), 7.80~7.71 (2H, m), 7.61~7.31 (11H, m), 7.20~7.11 (4H, m)1-54δ= 8.55 (1H, d), 8.36 (2H, m), 8.25~8.19 (4H, m), 8.08~7.92 (4H, m), 7.80 (1H, t), 7.52~7.39 (10H, m), 7.32~7.18 (16H, m)1-57δ= 8.55 (2H, m), 8.45~8.36 (4H, m), 8.20~8.19 (2H, m), 7.94~7.86 (5H, m), 7.56~7.49 (8H, m), 7.40 (1H, d), 7.31 (1H, t), 7.20~7.18 (4H, m)1-60δ= 8.55 (1H, d), 8.36~8.16 (7H, m), 8.06 (1H, d), 7.92 (1H, d), 7.80 (1H, t), 7.62~7.50 (11H, m), 7.40 (1H, d), 7.29~7.11 (9H, m)1-64δ= 8.55 (1H, d), 8.38~8.36 (3H, m), 8.20~8.19 (2H, m), 7.94~7.92 (3H, m), 7.80~7.41 (23H, m), 7.20~7.11 (4H, m)1-66δ= 8.55 (2H, m), 8.38~8.32 (2H, m), 8.20~8.17 (4H, m), 7.98~7.92 (4H, m), 7.80~7.71 (2H, m), 7.57~7.31 (14H, m), 7.20~7.11 (4H, m)1-72δ= 8.55 (2H, d), 8.46~8.38 (4H, m), 8.20 (3H, m), 8.00 (1H, s), 7.94~7.71 (6H, m), 7.56~7.40 (10H, m), 7.20~7.11 (8H, m)1-74δ= 8.55 (1H, d), 8.38~8.36 (3H, m), 8.20~8.19 (2H, m), 7.98~7.92 (4H, m), 7.80~7.71 (5H, m), 7.61~7.31 (13H, m), 7.20~7.11 (4H, m)1-94δ= 8.55 (1H, d), 8.36 (3H, m), 8.25~8.19 (5H, m), 7.94~7.92 (3H, m), 7.83 (1H, s), 7.71~7.49 (19H, m)1-97δ= 9.60 (1H, d), 9.27 (1H, s), 8.55 (2H, m), 8.45~8.32 (8H, m), 8.20 (1H, d), 7.92~7.31 (24H, m), 7.16~7.11 (2H, m)1-104δ= 8.55 (3H, m), 8.45~8.21 (8H, m), 7.94 (1H, s), 7.86 (1H, d), 7.71~7.50 (20H, m), 7.31 (1H, t), 7.16~7.08 (5H, m)1-107δ= 8.55 (1H, d), 8.38 (1H, d), 8.23~8.19 (3H, m), 7.98~7.92 (5H, m), 7.80~7.71 (4H, m), 7.55~7.31 (11H, m), 7.20~7.11 (4H, m)1-108δ= 8.55 (2H, m), 8.38 (1H, d), 8.23~8.19 (4H, m), 7.94~7.92 (4H, m), 7.80~7.40 (16H, m), 7.31 (1H, d), 7.20~7.11 (8H, m)1-109δ= 9.09 (1H, s), 8.55~8.50 (2H, m), 8.20~8.00 (11H, m), 7.80 (1H, t), 7.60~7.20 (15H, m)1-111δ= 8.97 (1H, d), 8.55 (1H, d), 8.25~8.20 (4H, m), 8.00~7.80 (7H, m), 7.69~7.63 (2H, m), 7.54~7.20 (14H, m)1-129δ= 9.08 (1H, d), 8.84 (1H, d), 8.55 (2H, d), 8.25~8.17 (6H, m), 8.05~7.90 (5H, m), 7.80~7.11 (32H, m)1-140δ= 8.90~8.89 (3H, m), 8.55 (2H, m), 8.32~8.19 (6H, m). 7.92~7.80 (6H, m), 7.70~7.11 (24H, m)1-152δ= 9.09 (1H, s), 8.55~8.45 (6H, m), 8.32~7.49 (26H, m), 7.31~7.11 (7H, m)1-161δ= 9.09 (1H, s), 8.55 (2H, m), 8.38 (1H, d), 8.20~7.92 (10H, m), 7.80~7.31 (12H, m), 7.20~7.18 (4H, m)1-165δ= 9.27 (1H, s), 8.79 (1H, d), 8.55 (2H, m), 8.45~8.30 (6H, m), 8.20~8.15 (3H, m), 7.70~7.49 (17H, m), 7.25~7.15 (4H, m)1-168δ= 9.27 (1H, s), 8.79 (1H, d), 8.55 (2H, m), 8.45~8.30 (4H, m), 8.20~8.16 (3H, m), 7.94~7.92 (2H, m), 7.82~7.40 (20H, m), 7.20~7.11 (6H, m)1-169δ= 8.97 (1H, d), 8.55 (1H, d), 8.38 (1H, d), 8.20 (2H, m), 8.00~7.80 (13H, m), 7.92~7.80 (12H, m), 7.52~7.31 (12H, m), 7.16~7.11 (4H, m)1-179δ= 8.97 (1H, d), 8.55 (2H, m), 8.38 (1H, d), 8.20~8.19 (3H, m), 8.00~7.40 (22H, m), 7.20~7.11 (8H, m)1-219δ= None (Deuteration 100%)1-220δ= 8.36 (2H, d), 8.25 (2H, d), 8.02~7.98 (3H, m), 7.64 (1H, s), 7.50~7.25 (10H, m)1-221δ= 8.55 (1H, d), 8.36 (2H, d), 8.20~8.19 (2H, m), 7.92~7.80 (3H, m), 7.58~7.40 (7H, m), 7.20~7.11 (4H, m)1-226δ= 8.55 (1H, d), 8.45~8.21 (8H, m), 7.94 (1H, s), 7.86 (1H, d), 7.71~7.47 (13H, m), 7.31 (1H, t)1-227δ= 8.76 (1H, s), 7.99 (1H, s), 7.78~7.77 (2H, s), 7.65~7.63 (3H, m), 7.52 (1H, d), 7.16 (1H, d)1-230δ= 8.55 (2H, m), 8.45~8.30 (7H, m), 8.19 (1H, d), 7.94 (1H, s), 7.86 (1H, d), 7.71~7.40 (12H, m), 7.19~7.10 (8H, m)1-231δ= 8.55 (2H, m), 8.45~8.36 (5H, m), 8.21~8.19 (2H, m), 8.02 (1H, d), 7.94 (1H, s), 7.86~7.76 (5H, m), 7.56~7.41 (12H, m), 7.20~7.11 (4H, m)2-1δ= 8.55 (1H, d), 8.30 (1H, d), 8.19~8.13 (2H, m), 7.99~7.89 (4H, m), 7.77 (1H, d), 7.62~7.50 (12H, m), 7.35(1H, t), 7.20~7.16 (2H, m)2-16δ= 9.05 (1H, s), 8.55 (1H, d), 8.33~8.13 (7H, m), 7.99~7.89 (5H, m), 7.77~7.50(13H, m), 7.35 (1H, t), 7.20~7.16 (2H, m)2-27δ= 8.55 (1H, m), 8.30 (1H, d), 8.21~8.13 (4H, m), 7.99~7.89 (4H, m), 7.77~7.35 (20H, m), 7.20~7.16 (2H, m)2-28δ= 8.55(1H, m), 8.18~8.09 (3H, m), 8.00~8.79 (2H, m), 7.87 (1H, m), 7.79~7.77 (4H, m), 7.69~7.63 (4H, m), 7.52~7.25 (12H, m)2-32δ= 8.55 (1H, m), 8.18~8.12 (2H, m), 8.00~7.87 (3H, m), 7.79~7.77 (6H, m), 7.69~7.63 (6H, m), 7.52~7.25 (14H, m)2-41δ= 8.55 (1H, m), 8.30 (1H, d), 8.19~8.13 (2H, m), 7.99~7.89(4H, m), 7.77(1H, d), 7.58~7.50(2H, m), 7.35 (1H, t), 7.20~7.16 (2H, m)2-61δ= 7.62~7.50 (10H, m)2-65δ= 7.79 (2H, m), 7.70~7.68 (3H, m), 7.58~7.41 (13H, m)2-68δ= 8.21 (2H, s), 7.75~7.60 (8H, m), 7.49~7.41 (8H, m)2-82δ= None (Deuteration 100%)2-88δ= None (Deuteration 100%)2-100δ= None (Deuteration 100%)3-1δ= 8.55 (2H, d), 7.62~7.50 (12H, m), 7.24 (2H, m), 7.16~7.11 (4H, m)3-4δ= 8.55 (2H, d), 7.94~7.91 (10H, m), 7.75 (4H, d), 7.49~7.35 (10H, m), 7.16 (2H, t)3-5δ= 8.55 (2H, d), 8.21 (1H, s), 7.94~7.91 (6H, m), 7.75~7.35 (16H, m), 7.26 (1H, d), 7.16 (2H, t)3-22δ= 8.55 (1H, d), 8.19 (1H, d), 7.94~7.91 (9H, m), 7.75 (4H, d), 7.58~7.35 (11H, m), 7.20~7.16 (2H, m)3-23δ= 8.55 (1H, d), 8.21~8.19 (2H, m), 7.94`7.91 (5H, m), 7.75~7.35 (18H, m), 7.20~7.16 (2H, m)3-32δ= 8.55 (1H, d), 8.19 (1H, d), 7.94~7.91 (9H, m), 7.75 (4H, d), 7.58~7.35 (11H, m), 7.20~7.16 (2H, m)3-35δ= 8.55 (1H, d), 8.21~8.19 (2H, m), 7.94~7.91 (5H, m), 7.68~7.35 (18H, m), 7.20~7.16 (2H, m)3-41δ= 8.55(2H, d), 7.94~7.91 (10H, m), 7.84 (2H, d), 7.75 (4H, d), 7.49~7.35 (8H, m), 7.16 (2H, t)3-61δ= 8.55 (2H, d), 7.94 (2H, d), 7.42~7.35 (4H, m), 7.16 (2H, t)3-69δ= 7.92~7.91 (8H, m), 7.75 (4H, d), 7.49~7.41 (6H, m)3-75δ= 7.79~7.73 (3H, m), 7.60~7.41 (12H, m), 7.25 (1H, d)3-77δ= None (Deuteration 100%)3-78δ= None (Deuteration 100%)3-91δ= None (Deuteration 100%).

[0630]

[0631] 화합물 번호FD-MS화합물 번호FD-MS1-1m / z= 640.23 (C 45 H 28N4O= 640.75)1-2m / z= 640.23 (C 45 H 28 N4O= 640.75)1-5m / z= 656.20 (C 45 H 28 N4S= 656.81)1-7m / z= 715.27 (C 51 H 33 N5= 715.86)1-14m / z= 822.25 (C 57 H 34 N4OS= 822.99)1-16m / z= 791.30 (C 57 H 37 N5= 791.96)1-18m / z= 805.28 (C 57 H 35 N5O= 805.94)1-25m / z= 732.23 (C 51 H 32 N4S= 732.91)1-26m / z= 732.23 (C 51 H 32 N4S= 732.91)1-31m / z= 772.27 (C 54 H 36 N4S= 772.97)1-35m / z= 896.30 (C 64 H 40 N4S= 897.11)1-39m / z= 792.29 (C 57 H 36 N4O= 792.94)1-47m / z= 762.19 (C 51 H 30 N4S2= 762.95)1-53m / z= 640.23 (C 45 H 28 N4O = 640.75)1-54m / z= 640.23 (C 45 H 28 N4O = 640.75)1-57m / z= 656.20 (C 45 H 28 N4S= 656.81)1-60m / z= 715.27 (C 51 H 33 N5= 715.86)1-64m / z= 792.29 (C 57 H 36 N4O= 792.94)1-66m / z= 822.25 (C57 H 34 N4OS= 822.99)1-72m / z= 821.26 (C 57 H 35 N5S= 822.00)1-74m / z= 716.26 (C 51 H 32 N4O= 716.84)1-94m / z= 792.29 (C 57 H 36 N4O= 792.94)1-97m / z= 882.28 (C 63 H 38 N4S= 883.09)1-104m / z= 897.29 (C 63 H 39 N5S= 898.10)1-107m / z= 639.23 (C 46 H 29 N 3O = 639.76)1-108m / z= 804.29 (C 58 H 36 N4O= 804.95)1-109m / z= 690.24 (C49H 30 N4O= 690.81)1-111m / z= 690.24 (C49H 30 N4O= 690.81)1-129m / z= 1057.38 (C 77 H 47 N 5O = 1058.26)1-140m / z= 994.31 (C 72 H 42 N4S= 995.22)1-152m / z= 964.27 (C 67 H40N4S2= 965.21)1-161m / z= 690.24 (C 49 H 30 N4O= 690.81)1-165m / z= 806.25 (C 57 H 34 N4S= 806.99)1-168m / z= 865.32 (C 63 H 39 N5= 866.04)1-169m / z= 690.24 (C 49 H 30 N4O= 690.81)1-179m / z= 855.30 (C 61 H 37N5O= 856.00)1-219m / z= 668.40 (C 45 D 28 N4O= 668.92)1-220m / z= 650.29 (C 45 H 18 D 10 N4O= 650.81)1-221m / z= 649.28 (C 45 H 19 D9N 4O = 649.80)1-226m / z= 911.38 (C 63 H 25 D 14 N5S= 912.19)1-227m / z= 831.41 (C 57 H9D 25 N4S= 832.14)1-230m / z= 732.23 (C 51 H 32 N4S= 732.91)1-231m / z= 732.23 (C 51 H 32 N4S= 732.91)2-1m / z= 484.59 (C 36 H 24 N2= 484.19)2-16m / z= 634.77 (C 48 H 30 N2= 634.24)2-27m / z= 712.88 (C 54 H 36 N2= 712.29)2-28m / z= 712.88 (C 54 H 36 N2= 712.29)2-32m / z= 636.78 (C 48 H 32 N2= 636.26)2-41m / z= 494.65 (C 36 H 14 D 10 N2= 494.26)2-61m / z= 498.68 (C 36 H 10 D 14 N2= 498.28)2-65m / z= 650.87 (C 48 H 18 D 14 N2= 650.34)2-68m / z= 650.87 (C 48 H 18 D14 N2= 650.34)2-82m / z= 668.98 (C 48 D 32 N2= 668.46)2-88m / z= 668.98 (C 48 D 32 N2= 668.46)2-100m / z= 680.95 (C 48 D 30 N2O= 680.42)3-1m / z= 408.16 (C 30 H 20 N2= 408.50)3-4m / z= 560.23 (C 42 H 28 N2= 560.70)3-5m / z= 560.23 (C 42 H 28 N2= 560.70)3-22m / z= 560.23 (C 42 H 28 N2= 560.70)3-23m / z= 560.23 (C 42 H 28 N2= 560.70)3-32m / z= 560.23 (C 42 H 28 N2= 560.70)3-35m / z= 560.23 (C 42 H 28 N2= 560.70)3-41m / z= 560.23 (C 42 H 28 N2= 560.70)3-61m / z= 578.34 (C 42 H 10 D 18 N2= 578.81)3-69m / z= 570.29 (C 42 H 18 D 10 N2= 570.76)3-75m / z= 584.27 (C 42 H 16 D 10 N2O= 584.74)3-77m / z= 588.40 (C 42 D 28 N2= 588.87)3-78m / z= 588.40 (C 42 D 28 N2= 588.87)3-91m / z= 668.46 (C 48 D32 N2= 668.99)

[0632]

[0633] Experimental Example 1.

[0634] Experimental Example 1-1. Fabrication of an Organic Light-Emitting Device

[0635] 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 (Ultraviolet Ozone) for 5 minutes using UV (Ultraviolet) in a UV (Ultraviolet) 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 vapor deposition.

[0636] A 600Å thick hole injection layer 4,4',4''-tris[2-naphthyl(phenyl)amino] triphenylamine (2-TNATA) and a 300Å thick hole transport layer N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) were deposited on the ITO transparent electrode (anode).

[0637]

[0638] On top of that, a light-emitting layer was thermally vacuum deposited as follows. The light-emitting layer used the compound described in Table 9 below as a host, and Ir(ppy)3(tris(2-phenylpyridine)iridium) was used as a green phosphorescent dopant. The host was doped with 7% Ir(ppy)3 and deposited to a thickness of 360 Å.

[0639] Afterwards, BCP was deposited as a hole blocking layer with a thickness of 60Å, and Alq3 was deposited as an electron transport layer with a thickness of 200Å on top of it. Finally, lithium fluoride (LiF) was deposited as an electron injection layer with a thickness of 10Å on the electron transport layer, and then aluminum (Al) was deposited as a cathode with a thickness of 1,200Å on the electron injection layer, thereby manufacturing an organic electroluminescent device.

[0640]

[0641] Meanwhile, all organic compounds required for OLED device production are 10 for each material. -6 ~10 -8 It was purified by vacuum sublimation under 10 torr and used in the production of OLED (Organic Light Emitting Device).

[0642]

[0643] Experimental Example 1-2. Driving Voltage and Luminous Efficiency of Organic Light-Emitting Devices

[0644] The electroluminescence (EL) characteristics of the organic light-emitting device 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 When, T 90 The results of measuring the driving voltage, luminous efficiency, color coordinates (CIE), and lifespan of the organic light-emitting device manufactured according to the present invention are shown in Table 9 below.

[0645] The above T 90 refers to the lifespan (unit: hours), which is the time it takes for the initial brightness to drop to 90%.

[0646]

[0647] Light-emitting layer compound driving voltage (V) luminous efficacy (cd / A) lifespan (T) 90)Embodiment 11-14.4067.9145Embodiment 21-24.3366.8138Embodiment 31-54.4267.7148Embodiment 41-74.4467.6140Embodiment 51-144.4567.3142Embodiment 61-164.2965.7135Embodiment 71-184.4267.4137Embodiment 81-254.4467.9150Embodiment 91-264.4268.4138Embodiment 101-314.4968.2147Embodiment 111-354.4067.2149Embodiment 121-394.3766.9142 Example 131-474.3265.1151 Example 141-534.5069.2175 Example 151-544.4468.6150 Example 161-574.5269.0179 Example 171-604.4368.0170 Example 181-644.5469.3183 Example 191-664.5369.2178 Example 201-724.5469.1182 Example 211-744.5269.4168 Example 221-944.4968.8185 Example 231-974.5969.3178 Example 241-1044.5068.0177 Example 251-1074.6267.2172 Example 261-1084.6567.7173 Example 271-1094.3365.0143 Example 281-1114.3264.8142 Example 291-1294.5463.2140 Example 301-1404.4764.4144 Example 311-1524.3765.4146 Example 321-1614.4865.2177 Example 331-1654.4965.7180 Example 341-1684.4465.3176 Example 351-1694.5265.6182 Example 361-1794.4764.8170 Example 371-2194.3968.0163 Example 381-2204.4168.1160 Example 391-2214.3767.6142 Example 401-2264.5168.3184 Example 411-2274.5165.9192 Example 421-2304.6269.8165 Example 431-2314.5969.5162 Comparative Example 1A4.6653.250 Comparative Example 2B4.7358.156Comparative example 3C4.6853.668Comparative example 4D5.2056.085Comparative example 5E4.7359.257Comparative example 6F5.1956.272Comparative example 7G5.0455.262.

[0648]

[0649] [Comparative example compound]

[0650]

[0651] As OLED panels are applied in various places, the structure and composition of the devices are becoming increasingly diverse. Accordingly, the concept of the host is also diversifying. The heterocyclic compound represented by the chemical formula 1 of the present invention is characterized by having weak electron transport (ET) characteristics as an n-type host. Therefore, in the organic light-emitting device, when the LUMO is reduced, the efficiency and lifespan can be dramatically increased. In addition, this host has the characteristic of very easily maintaining charge balance within the light-emitting layer when combined with a p-type host with weak hole transport (HT) characteristics. This is because the deviation according to the ratio of p-type and n-type is not large. In particular, in the case of a multi-stack structure rather than a single-layer structure, it is difficult to maintain charge balance within the device due to the nature of the OLED process, which requires stacking multiple layers by vacuum sublimation deposition with precisely adjusted thicknesses. Therefore, the structure of the heterocyclic compound represented by the chemical formula 1 of the present invention can be a great advantage.

[0652] Compound A of Comparative Example 1 is a compound in which triazine and carbazole are linked via meta-phenylene, and dibenzofuran is directly bonded to the triazine. Unlike Compound 1-2 of Example 2 linked via ortho-phenylene, Comparative Example 1 linked via meta-phenylene shows lower efficiency and lifetime than Example 2. LUMO is basically formed in triazine with strong electron transport (ET) properties, but when linked ortho-wise, like the heterocyclic compound represented by Chemical Formula 1 of the present invention, the LUMO is relatively reduced the most compared to the para or meta linkage form, and the separation from the HOMO formed on the carbazole side is the greatest. Therefore, when linked ortho-wise, like the heterocyclic compound represented by Chemical Formula 1 of the present invention, the HOMO and LUMO have the shallowest level values, and the energy gap (Eg) also has the largest level value compared to the meta linkage or para linkage. In addition, since the dihedral angle is the largest and the T1 value is also the highest, the triplet exciton confinement ability can be the best. This is because the T1 value must be higher than that of the dopant in order to prevent the tricentral exciton that flows from the host to the dopant from leaking back to the host, and the higher the value, the better the triplet exciton confinement ability. This importance becomes even greater, especially in the case of phosphorescent green or blue dopants with high T1 values. As a result, there is an advantage in that the efficiency and lifetime are superior when the ortho-phenylene linkage is compared to when the meta- or para-phenylene linkage is performed.

[0653] This can also be confirmed through the Gaussian calculation in Table 10 below, where it can be seen that the T1 value is significantly higher when the substituent in the part directly connected to the triazine is changed when it is an ortho connection than when it is a para or meta connection.

[0654]

[0655]

[0656]

[0657]

[0658] Compound B of Comparative Example 2 is a form in which triazine is linked by ortho-phenylene and dibenzofuran is directly bonded. Compared to Compound 1-2 of Example 2 in which triazine and dibenzofuran are linked by phenylene, in Compound B, the overlap between the charges of triazine and dibenzofuran is strengthened due to the absence of phenylene between the triazine and dibenzofuran. When the HOMO and LUMO are separated to some extent rather than strongly overlapped, intramolecular charge transfer (CT) can occur smoothly without loss. This varies slightly depending on the shape of the molecule, and when the intramolecular charge transfer distance is well controlled, the effect of increasing efficiency and lifetime can be observed. It is interpreted that the efficiency and lifetime of Compound B of Comparative Example 2 are reduced due to this difference.

[0659] Compound C of Comparative Example 3 is similar to the heterocyclic compound represented by Chemical Formula 1 of the present invention in that it is connected between triazine and dibenzofuran via phenylene, but differs in the meta-phenylene connection point. It is interpreted that the low T1 value and deep LUMO value due to the meta-phenylene connection between triazine and carbazole resulted in a decrease in efficiency and lifespan.

[0660] Compound D of Comparative Example 4 does not contain a heteroaryl group like the heterocyclic compound represented by the above-described chemical formula 1 of the present invention, but contains only an aryl group instead of a heteroaryl group. Comparative Example 4 showed a higher driving voltage and lower efficiency than the examples. This is interpreted as being due to the absence of the heteroaryl group weakening the π-π interaction between molecules, significantly slowing down the rate of charge transfer between molecules, and thus lowering the exciton generation efficiency due to the imbalance of holes and electrons within the light-emitting layer.

[0661] Meanwhile, when comparing compounds 1-5 of Example 3 with compound E of Comparative Example 5, it can be confirmed that compound E of Comparative Example 5 is connected to the 3-position of dibenzofuran instead of the aryl group as Ar1, which expands the LUMO and consequently reduces the efficiency and lifespan.

[0662] Compound F of Comparative Example 6 has a structure in which carbazole, where Ar1 is a heteroaryl group, is directly bonded. Compound F has a nitrogen atom of carbazole directly bonded to triazine, which increases the dihedral angle and increases the T1 value. However, since it has an sp3 nitrogen atom, the nitrogen of carbazole, which has hole transport (HT) characteristics, is directly bonded to triazine, which has strong electron transport (ET) characteristics, and this characteristic is greatly weakened. As a result, it can be seen that the HOMO level becomes excessively deep, and the driving voltage is measured to be relatively high. In addition, since the CN bond, which is relatively weaker than the C-C bond, is directly bonded to the triazine, when the device operates and is continuously subjected to electrical stress, the CN bond portion of the carbazole and triazine, which have low bond dissociation energy, may be broken. As a result, the driving voltage may increase, and the efficiency and lifespan may be reduced.

[0663] Compound G of Comparative Example 7 is interpreted to have reduced efficiency and lifespan due to the intramolecular charge transfer distance being too close due to strong charge overlap between triazine and dibenzothiophene.

[0664]

[0665] Experimental example 2.

[0666] An organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1, except that the light-emitting layer was deposited from a single source after preliminarily mixing one type of first host (compound of chemical formula 1) and one type of second host (compound of chemical formula 2 or 3) described in Table 11 below.

[0667]

[0668] Experimental Example 2-2. Driving Voltage and Luminous Efficiency of Organic Light-Emitting Devices

[0669] The electroluminescence (EL) characteristics of the organic light-emitting device 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 When, T 90 The results of measuring the driving voltage, luminous efficiency, color coordinates (CIE), and lifespan of the organic light-emitting device manufactured according to the present invention are shown in Table 11 below.

[0670] The above T 90 refers to the lifespan (unit: hours), which is the time it takes for the initial brightness to drop to 90%.

[0671]

[0672] Emitting layer compound ratio driving voltage (V) luminous efficacy (cd / A) lifespan (T 90)Embodiment 441-1:2-15:14.0770.1151Embodiment 451-1:2-12:14.1370.7166Embodiment 461-1:2-11:14.1871.3203Embodiment 471-1:2-11:24.3175.1254Embodiment 481-1:2-11:54.3967.1183Embodiment 491-5:2-162:14.2570.9170Embodiment 501-5:2-161:14.3071.5207Embodiment 511-5:2-161:24.4375.3259Embodiment 521-7:2-652:14.2670.9207 Example 531-7:2-651:14.3171.5252 Example 541-7:2-651:24.4475.3315 Example 551-25:2-822:14.1370.7216 Example 561-25:2-821:14.1871.3263 Example 571-25:2-821:24.3175.1329 Example 581-47:2-882:14.1668.6222 Example 591-47:2-881:14.2169.2271 Example 601-47:2-881:24.3472.9339 Example 611-57:2-1002:14.1373.3230 Example 621-57:2-1001:14.1873.9281 Example 631-57:2-1001:24.3177.8351 Example 641-94:3-12:14.1370.9217 Example 651-94:3-11:14.1871.5265 Example 661-94:3-11:24.3175.3331 Example 671-109:3-52:13.9968.9189 Example 681-109:3-51:14.0469.5230 Example 691-109:3-51:24.1673.2288 Example 701-165:3-222:14.1068.6214 Example 711-165:3-221:14.1569.2261 Example 721-165:3-221:24.2772.9326 Example 731-219:3-752:14.0471.9190 Example 741-219:3-751:14.0972.5232 Example 751-219:3-751:24.2176.3290 Example 761-226:3-782:14.0671.9220 Example 771-226:3-781:14.1172.5268 Example 781-226:3-781:24.2376.3335 Example 791-230:3-912:14.3072.0198 Example 801-230:3-911:14.3572.6241 Example 811-230:3-911:24.4876.4301 Comparative Example 8A:2-12:14.5562.575 Comparative Example 9A:2-11:14.6163.891 Comparative Example 10A:2-11:24.6764.3114 Comparative Example 11B:3-352:14.6664.589 Comparative Example 12B:3-351:14.7365.9102 Comparative Example 13B:3-351:24.7966.4121Comparative example 14D:3-12:15.1062.2102Comparative example 15D:3-11:15.1663.1125Comparative example 16D:3-11:25.2163.8146.

[0673]

[0674] [Comparative example compound]

[0675]

[0676] From the results in Table 11 above, it was confirmed that when the heterocyclic compound represented by the chemical formula 1 of the present invention was used as an N-type host, and the heterocyclic compound represented by the chemical formula 2 or the heterocyclic compound represented by the chemical formula 3 was used as a P-type host and the two hosts were mixed and deposited, the driving voltage, luminous efficiency, and lifespan of the organic light-emitting device were improved.

[0677] From this, it can be expected that when the above two compounds are mixed and deposited, an exciplex phenomenon will occur.

[0678] The above exciplex phenomenon is a phenomenon in which energy of the size of the HOMO energy level of the donor (P-TYPE host) and the LUMO energy level of the acceptor (N-TYPE host) is released due to electron exchange between two molecules. When the exciplex phenomenon between two molecules occurs, reverse intersystem crossing (RISC) occurs, and this can increase the internal quantum efficiency of fluorescence up to 100%. When a donor (P-type host) with a good hole transport ability and an acceptor (N-type host) with a good electron transport ability are used as the host of the light-emitting layer, holes are injected into the P-type host and electrons are injected into the N-type host, so the driving voltage of the organic light-emitting device can be lowered, and thus the lifespan of the organic light-emitting device can be improved.

[0679] Furthermore, it was confirmed that the replacement of deuterium resulted in improved lifetime characteristics. This suggests that even with similar structures, the properties of compounds can differ depending on the substitution of deuterium. Since the single bond dissociation energy of carbon and deuterium is higher than that of carbon and hydrogen, it can be confirmed that the increased thermal stability of the molecule leads to improved device lifetime.

[0680]

[0681] [Explanation of symbols]

[0682] 100: Substrate

[0683] 200: Bipolar

[0684] 300: Organic layer

[0685] 301: Hole injection layer

[0686] 302: Hole transport layer

[0687] 303: Emissive layer

[0688] 304: Hole blocking layer

[0689] 305: Electron transport layer

[0690] 306: Electron injection layer

[0691] 400: Cathode

Claims

1. A heterocyclic compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, The above X1 is N; or CRa, The above X2 is N; or CRb, The above X3 is N; or CRc, At least two of the above X1 to X3 are N, The above Y1 is O; S; or NRd, The above R1 to R5 and Ra to Rd are the same as or different from each other, and are each independently 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; -SiR101R102R103; And -NR101R102, 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, The above a1 is an integer from 0 to 4, and when a1 is 2 or greater, R1 is equal to or different from each other, The above a2 is an integer from 0 to 4, and when a2 is 2 or greater, R2 is equal to or different from each other, The above a3 is an integer from 0 to 4, and when a3 is 2 or greater, R3 is equal to or different from each other, The above a4 is an integer from 0 to 3, and when a4 is 2 or greater, R4 is equal to or different from each other, The above a5 is an integer from 0 to 4, and when a5 is 2 or greater, R5 is equal to or different from each other, The above Ar1 is a substituted or unsubstituted C6 to C60 aryl group, The above L1 and L2 are the same as or different from each other, and each independently represents a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a C2 to C60 heteroarylene group, The above a6 is an integer from 0 to 5, and if a6 is 2 or greater, L1 is equal to or different from each other, The above a7 is an integer from 0 to 5, and if a7 is 2 or greater, L2 is equal to or different from each other, The above L3 is a substituted or unsubstituted C6 to C60 arylene group; or a C2 to C60 heteroarylene group, The above a8 is an integer from 1 to 5, and when a8 is 2 or greater, L3 are equal to or different from each other.

2. In paragraph 1, The heterocyclic compound represented by the above chemical formula 1 is a heterocyclic compound represented by any one of the following chemical formulas 1-1 to 1-4: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] In the above chemical formulas 1-1 to 1-4, The above X1 to X3, Y1, R1 to R5, L1 to L3, Ar1 and a1 to a8 are the same as defined in the above chemical formula 1.

3. In paragraph 1, Above A heterocyclic compound represented by any one of the following chemical formulas A-1 to A-3: [Chemical Formula A-1] [Chemical Formula A-2] [Chemical Formula A-3] In the above chemical formulas A-1 to A-3, The above Y11 is O; or S, wherein R11 to R15 and Re are the same as or different from each other, and each independently represent hydrogen; deuterium; halogen; 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 -NR101R102, wherein R101, R102 and R103 are the same as or different from each other, and each independently represents 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 above b1 is an integer from 0 to 8, and when b1 is 2 or greater, R11 is equal to or different from each other, The above b2 is an integer from 0 to 4, and when b2 is 2 or greater, R12 is equal to or different from each other, The above b3 is an integer from 0 to 6, and when b3 is 2 or greater, R13 is equal to or different from each other, The above b4 is an integer from 0 to 4, and when b4 is 2 or greater, R14 is equal to or different from each other, The above b5 is an integer from 0 to 6, and when b5 is 2 or greater, R15 is equal to or different from each other, The above L1 and a6 are identical to the definitions in the above chemical formula 1.

4. In paragraph 1, Above A heterocyclic compound represented by any one of the following chemical formulas B-1 to B-3: [Chemical Formula B-1] [Chemical Formula B-2] [Chemical Formula B-3] In the above chemical formulas B-1 to B-3, The above Y21 is O; or NRf, The above R21 to R23 and Rf are the same as or different from each other, and are each independently 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; -SiR101R102R103; And -NR101R102, wherein R101, R102 and R103 are the same as or different from each other, and each independently represents 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 above c1 is an integer from 0 to 4, and when c1 is 2 or greater, R21 is equal to or different from each other, The above c2 is an integer from 0 to 6, and when c2 is 2 or greater, R22 is equal to or different from each other, The above c3 is an integer from 0 to 6, and when c3 is 2 or greater, R23 is equal to or different from each other, The definitions of Y1, R4, L3, a4 and a8 above are the same as in Chemical Formula 1.

5. In paragraph 1, The heterocyclic compound represented by the above chemical formula 1 is a heterocyclic compound which does not contain deuterium as a substituent or has a deuterium content of 1% to 100% with respect to 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 An organic light-emitting device comprising at least one organic layer provided between the first electrode and the second electrode, An organic light-emitting device, wherein at least one of the organic layers comprises the heterocyclic compound of claim 1.

8. In paragraph 7, The above organic layer includes a light-emitting layer, An organic light-emitting device, wherein the light-emitting layer comprises a heterocyclic compound of claim 1.

9. In paragraph 7, The above organic layer includes a light-emitting layer, The above light-emitting layer comprises a host material, An organic light-emitting device, wherein the host material comprises a heterocyclic compound of claim 1.

10. In paragraph 7, An organic light-emitting device, wherein the organic layer further comprises a heterocyclic compound represented by the following chemical formula 2 or chemical formula 3: [Chemical formula 2] [Chemical Formula 3] In the above chemical formulas 2 and 3, The above R31, R32, R41 and R42 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)R201R202; -SiR201R202R203; And -NR201R202, 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 R201, R202 and R203 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, The above d1 is an integer from 0 to 7, and when d1 is 2 or greater, R31 is equal to or different from each other, The above d2 is an integer from 0 to 7, and when d2 is 2 or greater, R32 are equal to or different from each other, The above e1 is an integer from 0 to 6, and when e1 is 2 or greater, R41 is equal to or different from each other, The above e2 is an integer from 0 to 4, and when e2 is 2 or greater, R42 is equal to or different from each other, The above Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and are each independently a cyano group; -SiR201R202R203; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, and the above R201, R202 and R203 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, The above L11, L12, L21 and L22 are the same as or different from each other, and each independently represents a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, The above d3 is an integer from 0 to 5, and when d3 is 2 or greater, L11 is equal to or different from each other, The above d4 is an integer from 0 to 5, and when d4 is 2 or greater, L12 are equal to or different from each other, The above e3 is an integer from 0 to 5, and when e3 is 2 or greater, L21 are equal to or different from each other, The above e4 is an integer from 0 to 5, and when e4 is 2 or greater, L22 are equal to or different from each other.

11. In paragraph 10, The heterocyclic compound represented by the above chemical formula 2 is an organic light-emitting device represented by any one of the following compounds: .

12. In paragraph 10, The heterocyclic compound represented by the above chemical formula 3 is an organic light-emitting device represented by any one of the following chemical formulas 3-1 to 3-6: [Chemical Formula 3-1] [Chemical Formula 3-2] [Chemical Formula 3-3] [Chemical Formula 3-4] [Chemical Formula 3-5] [Chemical Formula 3-6] In the chemical formulas 3-1 to 3-6 above, The above R41, R42, Ar21, Ar22, L21, L22 and e1 to e4 are the same as defined in the above chemical formula 3.

13. In paragraph 10, The heterocyclic compound represented by the above chemical formula 3 is an organic light-emitting device represented by any one of the following compounds: .

14. In paragraph 10, An organic light-emitting device in which the heterocyclic compound represented by the chemical formula 2 above or the heterocyclic compound represented by the chemical formula 3 does not contain deuterium as a substituent or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms is 1% to 100%.

15. 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, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

16. Composition for an organic layer comprising a heterocyclic compound represented by the chemical formula 1 of paragraph 1 and a heterocyclic compound represented by the chemical formula 2 or 3 below: [Chemical formula 2] [Chemical Formula 3] In the above chemical formulas 2 and 3, The above R31, R32, R41 and R42 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)R201R202; -SiR201R202R203; And -NR201R202, 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 R201, R202 and R203 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, The above d1 is an integer from 0 to 7, and when d1 is 2 or greater, R31 is equal to or different from each other, The above d2 is an integer from 0 to 7, and when d2 is 2 or greater, R32 are equal to or different from each other, The above e1 is an integer from 0 to 6, and when e1 is 2 or greater, R41 is equal to or different from each other, The above e2 is an integer from 0 to 4, and when e2 is 2 or greater, R42 is equal to or different from each other, The above Ar11, Ar12, Ar21 and Ar22 are the same as or different from each other, and are each independently a cyano group; -SiR201R202R203; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, and the above R201, R202 and R203 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, The above L11, L12, L21 and L22 are the same as or different from each other, and each independently represents a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, The above d3 is an integer from 0 to 5, and when d3 is 2 or greater, L11 is equal to or different from each other, The above d4 is an integer from 0 to 5, and when d4 is 2 or greater, L12 are equal to or different from each other, The above e3 is an integer from 0 to 5, and when e3 is 2 or greater, L21 are equal to or different from each other, The above e4 is an integer from 0 to 5, and when e4 is 2 or greater, L22 are equal to or different from each other.

17. In paragraph 16, A composition for an organic layer, wherein the weight ratio of the heterocyclic compound represented by the chemical formula 1 above to the heterocyclic compound represented by the chemical formula 2 or 3 above is 1:9 to 9:1.

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