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

Abstract

The present invention provides a heterocyclic compound represented by Chemical Formula 1, an organic light emitting device including the heterocyclic compound, and a composition for an organic material layer. Each substituent of Chemical Formula 1 has the same definition as described in the specification of the disclosure.

Description

Technical Field

[0001] The present invention relates to a heterocyclic compound, an organic light-emitting device comprising the heterocyclic compound, and a composition for an organic material layer. Background Art

[0002] Organic light-emitting devices are self-luminous display devices with the advantages of wide viewing angle, fast response speed and good contrast.

[0003] An organic light-emitting device has a structure in which an organic thin film is arranged between two electrodes. When a voltage is applied to an organic light-emitting device having such a structure, electrons and holes injected from the two electrodes combine and pair in the organic thin film, and then emit light as they are annihilated. The organic thin film can be formed into a single layer or multiple layers as needed.

[0004] The material of the organic film may have a light-emitting function as required. For example, as the material of the organic film, compounds that can each form a light-emitting layer alone can be used, and compounds that can each serve as a host or dopant of a host-dopant type light-emitting layer can also be used. In addition, compounds that can perform hole injection, hole transport, electron blocking, hole blocking, electron transport, electron injection, etc. can also be used as the material of the organic film.

[0005] In order to improve the performance, lifetime or efficiency of organic light emitting devices, there is a constant need to develop organic thin film materials.

[0006] Prior art literature

[0007] Patent Literature

[0008] (Patent Document 1) U.S. Patent No. 4,356,429 Summary of the invention

[0009] The present invention is directed to providing a heterocyclic compound, an organic light-emitting device comprising the heterocyclic compound, and a composition for an organic material layer.

[0010] One embodiment of the present application provides a heterocyclic compound represented by the following Chemical Formula 1.

[0011] [Chemical formula 1]

[0012]

[0013] In Chemical Formula 1,

[0014] A1 to A4 and B1 to B6 are the same as or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1-C60 alkyl; substituted or unsubstituted C2-C60 alkenyl; substituted or unsubstituted C2-C60 alkynyl; substituted or unsubstituted C1-C60 alkoxy; substituted or unsubstituted C3-C60 cycloalkyl; substituted or unsubstituted C2-C60 heterocycloalkyl; substituted or unsubstituted C6-C60 aryl; substituted or unsubstituted C2-C60 heteroaryl; and a group represented by the following Chemical Formula 2, and at least one of A1 to A4 and B1 to B4 is represented by the following Chemical Formula 2, and

[0015] When any one of A1 to A4 is a group represented by the following Chemical Formula 2, any one of B1 to B4 is represented by a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group, or

[0016] When any one of B1 to B4 is a group represented by the following Chemical Formula 2, any one of A1 to A4 is represented by a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group,

[0017] [Chemical formula 2]

[0018]

[0019] In chemical formula 2,

[0020] Ar1 and Ar2 are the same as or different from each other and are each independently a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group,

[0021] L1 to L3 are the same as or different from each other and are each independently a single bond; a substituted or unsubstituted C6-C60 arylene group; or a substituted or unsubstituted C2-C60 heteroarylene group,

[0022] m1 and m2 are integers from 0 to 5, and

[0023] n1 to n3 are the same as or different from each other, and are each independently an integer of 0 to 4.

[0024] In addition, an embodiment of the present application provides an organic light-emitting device, comprising: a first electrode; a second electrode arranged opposite to the first electrode; and one or more organic material layers arranged between the first electrode and the second electrode, wherein one or more layers of the organic material layer include a heterocyclic compound represented by Chemical Formula 1.

[0025] In addition, one embodiment of the present application provides an organic light-emitting device, wherein the organic material layer including the heterocyclic compound of Chemical Formula 1 further includes a heterocyclic compound represented by the following Chemical Formula 5.

[0026] [Chemical formula 5]

[0027]

[0028] In Chemical Formula 5,

[0029] Y1 to Y3 are the same as or different from each other and are each independently CH or N, at least one of Y1 to Y3 is N,

[0030] L3 to L6 are the same as or different from each other and are each independently a single bond; a substituted or unsubstituted C6-C60 arylene group; or a substituted or unsubstituted C2-C60 heteroarylene group,

[0031] Ar4 to Ar6 are the same as or different from each other, and are each independently a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group,

[0032] m3 to m5 are the same as or different from each other and are each independently an integer from 0 to 5,

[0033] n6 to n9 are the same as or different from each other and are each independently an integer from 0 to 4,

[0034] p is an integer of 0 or 1,

[0035] Ra and Rb are the same as or different from each other and are each hydrogen; or deuterium,

[0036] a is an integer from 0 to 4,

[0037] b is an integer from 0 to 6, and

[0038] When p is 0, b is an integer from 0 to 4.

[0039] In addition, another embodiment of the present application provides a composition for an organic material layer, the composition including: a heterocyclic compound represented by Chemical Formula 1; and a heterocyclic compound represented by Chemical Formula 5.

[0040] The heterocyclic compound according to one embodiment can be used as an organic material layer material of an organic light-emitting device. The compound can play the role of hole injection layer material, electron blocking layer material, hole transport layer material, light-emitting layer material, electron transport layer material, hole blocking layer material, 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.

[0041] The heterocyclic compound can be used as a light-emitting material alone or in a mixture with an N-type host, and can be used as a host material or a dopant material of a light-emitting layer.

[0042] In particular, the heterocyclic compound represented by Chemical Formula 1 has a naphtho[2,1-b]benzofuran functional group. The structure of naphtho[2,1-b]benzofuran functional group has a high glass transition temperature. Therefore, due to the high thermal stability in the molecule, the life characteristics of the organic light-emitting device can be enhanced.

[0043] When naphtho[2,1-b]benzofuran is used alone, a planar structure of the molecule develops and the molecule is easy to crystallize. When a material that is easy to crystallize is used in an organic light-emitting device, the material crystallizes due to the Joule heat generated during the driving of the device, which reduces the life of the device. In the heterocyclic compound represented by Chemical Formula 1 according to the present disclosure, naphtho[2,1-b]benzofuran is not used alone, and naphtho[2,1-b]benzofuran is substituted by an aryl group (or a heteroaryl group) and an aromatic amine group represented by Chemical Formula 2 to distort the molecular structure, thereby preventing the molecule from crystallizing.

[0044] Furthermore, since the hole transport characteristics can be variously controlled by introducing various functional groups into Ar1 or Ar2 of Chemical Formula 2, there is an advantageous effect of adjusting the charge balance even if any common layer is used in the organic light emitting device.

[0045] Therefore, when the compound represented by Chemical Formula 1 is used for an organic material layer, the driving voltage of an organic light-emitting device may be reduced, the light emission efficiency thereof may be improved, and the lifespan characteristics of the organic light-emitting device may be improved due to the thermal stability of the compound. BRIEF DESCRIPTION OF THE DRAWINGS

[0046] Figures 1 to 3 Each of them is a diagram schematically showing a stacked structure of an organic light emitting device according to an embodiment of the present disclosure.

[0047] [reference numerals]

[0048] 100: Substrate

[0049] 200: Positive

[0050] 300: Organic material layer

[0051] 301: Hole injection layer

[0052] 302: Hole transport layer

[0053] 303: Luminous layer

[0054] 304: Hole blocking layer

[0055] 305: Electron transport layer

[0056] 306: Electron injection layer

[0057] 400: Negative DETAILED DESCRIPTION

[0058] Hereinafter, the present disclosure will be described in more detail.

[0059] In this specification, the term "substitution" means changing a hydrogen atom bonded to a carbon atom of a compound to another substituent. The position of substitution can be any position where a hydrogen atom is substituted, that is, a position where a substituent can replace. In the case of substitution by two or more substituents, the two or more substituents may be the same as or different from each other.

[0060] In the present specification, "substituted or unsubstituted" means substituted with one or more substituents selected from the group consisting of deuterium; halogen; cyano; C1-C60 straight or branched alkyl; C2-C60 straight or branched alkenyl; C2-C60 straight or branched alkynyl; C3-C60 monocyclic or polycyclic cycloalkyl; C2-C60 monocyclic or polycyclic heterocycloalkyl; C6-C60 monocyclic or polycyclic aryl; C2-C60 monocyclic or polycyclic heteroaryl; -SiRR'R"; -P(=O)RR'; C1-C20 alkylamine; C6-C60 monocyclic or polycyclic aromatic amine; and C2-C60 monocyclic or polycyclic heteroaromatic amine, or is unsubstituted, or is substituted with substituents connected by two or more substituents selected from the above-exemplified substituents, or is unsubstituted.

[0061] In the present specification, the "number of protons" refers to the number of substituents which a specific compound may have, and specifically, the number of protons may refer to the number of hydrogen atoms.

[0062] For example, unsubstituted benzene can be represented as having 5 protons, unsubstituted naphthyl can be represented as having 7 protons, naphthyl substituted with phenyl can be represented as having 6 protons, and unsubstituted biphenyl can be represented as having 9 protons.

[0063] In the present specification, halogen may be fluorine, chlorine, bromine or iodine.

[0064] In the present specification, the alkyl group includes a linear or branched form having 1 to 60 carbon atoms, and may be further substituted with other substituents. The number of carbon atoms in the alkyl group may be 1 to 60, specifically 1 to 40, and more specifically 1 to 20. Specific examples of the alkyl group may include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.

[0065] In this specification, alkenyl includes straight or branched forms with 2 to 60 carbon atoms, and can be further substituted by other substituents. The carbon number of alkenyl can be 2 to 60, particularly 2 to 40, more particularly 2 to 20. The specific example of alkenyl can include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-base, 2-phenylvinyl-1-base, 2,2-diphenylvinyl-1-base, 2-phenyl-2-(naphthyl-1-base)vinyl-1-base, 2,2-bis(diphenyl-1-base)vinyl-1-base, stilbenyl, styrenyl etc., but are not limited thereto.

[0066] In the present specification, the alkynyl group includes a straight chain or branched form having 2 to 60 carbon atoms, and may be further substituted with other substituents. The number of carbon atoms in the alkynyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20.

[0067] In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20. Specific examples of the alkoxy group may include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc., but are not limited thereto.

[0068] In this specification, cycloalkyl includes monocyclic or polycyclic groups with carbon atoms of 3 to 60, and may also be further substituted by other substituents. In this article, polycyclic groups refer to groups in which cycloalkyl is directly connected or fused to another cyclic group. In this article, other cyclic groups may be cycloalkyl, but may also be different types of cyclic groups such as heterocycloalkyl, aryl and heteroaryl. The carbon number of cycloalkyl may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20. Specific examples of cycloalkyl may include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc., but are not limited thereto.

[0069] In this specification, heterocycloalkyl includes O, S, Se, N or Si as heteroatoms, includes monocyclic or polycyclic groups with carbon number of 2 to 60, and may further be substituted by other substituents. In this article, polycyclic groups refer to groups that heterocycloalkyl is directly connected or fused to another cyclic group. In this article, other cyclic groups can be heterocycloalkyl, but can also be different types of cyclic groups such as cycloalkyl, aryl and heteroaryl. The carbon number of heterocycloalkyl can be 2 to 60, specifically 2 to 40, more specifically 3 to 20.

[0070] In this specification, aryl includes monocyclic or polycyclic groups with 6 to 60 carbon atoms, and may be further substituted by other substituents. In this article, polycyclic groups refer to groups in which aryl is directly connected or fused to another cyclic group. In this article, other cyclic groups may be aryl, but may also be different types of cyclic groups such as cycloalkyl, heterocycloalkyl and heteroaryl. Aryl may include spiro. The carbon number of aryl may be 6 to 60, specifically 6 to 40, more specifically 6 to 25. Specific examples of the aryl group may include phenyl, biphenyl, terphenyl, naphthyl, anthryl, chrysenyl, phenanthrenyl, perylenyl, fluoranthenyl, triphenylenyl, phenalenyl, pyrenyl, tetracenyl, pentacenyl, fluorenyl, indenyl, acenaphthylenyl, benzofluorenyl, spirobifluorenyl, 2,3-dihydro-1H-indenyl, and condensed ring groups thereof, but are not limited thereto.

[0071] In this specification, the phosphine oxide group is represented by -P(=O)R101R102, wherein R101 and R102 are the same or different from each other, and can be independently formed with hydrogen; deuterium; halogen group; alkyl; alkenyl; alkoxy; cycloalkyl; aryl; and a substituent of at least one of a heterocyclic group. Specifically, the phosphine oxide group can be substituted with an aryl group, and as the aryl group, the above examples can be applied. Examples of the phosphine oxide group may include a diphenylphosphine oxide group, a dinaphthylphosphine oxide group, etc., but are not limited thereto.

[0072] In this specification, a silyl group is a substituent group containing Si and directly connecting the Si atom as a group, represented by -SiR101R102R103. R101 to R103 are the same or different from each other, and can be independently a substituent group formed with 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 silyl groups may include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc., but are not limited thereto.

[0073] In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

[0074] When the fluorenyl group is substituted, the following structural formula and the like may be included, however, the structure is not limited thereto.

[0075]

[0076] In this specification, a spiro group is a group having a spiro structure and may have 15 to 60 carbon atoms. For example, a spiro group may include a structure in which a 2,3-dihydro-1H-indenyl or a cyclohexane spiro is bonded to a fluorenyl group. Specifically, a spiro group may include any one of the groups of the following structural formulas.

[0077]

[0078] In this specification, heteroaryl includes S, O, Se, N or Si as heteroatoms, includes monocyclic or polycyclic groups with carbon number of 2 to 60, and may be further substituted by other substituents. In this article, polycyclic groups refer to groups in which heteroaryl is directly connected or fused to another cyclic group. In this article, other cyclic groups may be heteroaryl, but may also be different types of cyclic groups such as cycloalkyl, heterocycloalkyl and aryl. The carbon number of heteroaryl can be 2 to 60, specifically 2 to 40, more specifically 3 to 25. Specific examples of heteroaryl groups may include pyridyl, pyrrolyl, pyrimidyl, pyridazinyl, furanyl, thiophenyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, lyl, furazanyl, oxadiazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiopyranyl, diazinyl, oxazinyl, thiazinyl, dioxynyl, triazinyl, tetrazinyl nyl), quinolyl, isoquinolyl, quinazolinyl, isoquinazolinyl, quinozolinyl, naphthyridyl, acridinyl, phenanthridinyl, imidazopyridyl, diazanaphthalenyl, triazaindenyl, 2-indolyl, indolizinyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, benzothiophenyl, benzofuranyl, dibenzothiophenyl, dibenzofuranyl,carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenazinyl, dibenzosilole, spirobi(dibenzosilole), dihydrophenazinyl, phenoxazinyl, phenanthridyl, thienyl ienyl), indolo[2,3-a]carbazolyl, indolo[2,3-b]carbazolyl, indolinyl, 10,11-dihydro-dibenzo[b,f]azepinyl, 9,10-dihydroacridinyl, phenanthridine azinyl), phenothiazinyl, phthalazinyl, naphthylidinyl, phenanthrolinyl, benzo[c][1,2,5]thiadiazolyl, 5,10-dihydrodibenzo[b,e][1,4]azasilinyl, pyrazolo[b,e][1,4] [1,5-c]quinazolinyl, pyrido[1,2-b]indazolyl, pyrido[1,2-a]imidazo[1,2-e]indolinyl, 5,11-dihydroindeno[1,2-b]carbazolyl, etc., but not limited thereto.

[0079] 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 may include methylamine, dimethylamine, ethylamine, diethylamine, anilamine, naphthylamine, benzylamine, dibenzylamine, anthracenylamine, 9-methylanthrylamine, diphenylamine, phenylnaphthylamine, ditolylamine, phenyltolylamine, triphenylamine, biphenylnaphthylamine, phenylbiphenylamine, biphenylfluorenylamine, phenylbiphenyltriphenylamine, biphenyltriphenylenylamine, etc., but are not limited thereto.

[0080] In this specification, arylene refers to an aryl group having two bonding sites, i.e., a divalent group. The description of aryl provided above is applicable to arylene groups except those that are each a divalent group. In addition, heteroarylene refers to a heteroaryl group having two bonding sites, i.e., a divalent group. The description of heteroarylene provided above is applicable to heteroarylene groups except those that are each a divalent group.

[0081] In this specification, an "adjacent" group may mean a substituent that replaces an atom directly connected to the atom substituted by the corresponding substituent, a substituent that is closest in space to the corresponding substituent, or another substituent that replaces the atom substituted by the corresponding substituent. For example, two substituents substituted at the ortho position in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring can be interpreted as groups that are "adjacent" to each other.

[0082] In the present disclosure, “a case where no substituent is indicated in a chemical formula or compound structure” means that a hydrogen atom is bonded to a carbon atom. However, due to the deuterium ( 2 H) is an isotope of hydrogen, so some of the hydrogen atoms may be deuterium.

[0083] In one embodiment of the present disclosure, "a situation where no substituent is indicated in a chemical formula or a compound structure" may mean that all positions where a substituent may appear are hydrogen or deuterium. In other words, since deuterium is an isotope of hydrogen, some hydrogen atoms may be deuterium as an isotope, and in this article, the content of deuterium may be from 0% to 100%.

[0084] In one embodiment of the present disclosure, in the case where “no substituent is indicated in the chemical formula or compound structure”, when deuterium is not explicitly excluded (for example, “the deuterium content is 0%”, “the hydrogen content is 100%” or “the substituents are all hydrogen”), hydrogen and deuterium can be used interchangeably in the compound.

[0085] In one embodiment of the present disclosure, deuterium is one of the isotopes of hydrogen, and is an element formed by 1 proton and 1 neutron as a nucleus, which can be represented by hydrogen-2, and its element symbol can also be written as D or 2 H.

[0086] In one embodiment of the present disclosure, isotopes refer to atoms having the same atomic number (Z) but different mass numbers (A), and may also be interpreted as elements having the same number of protons but different numbers of neutrons.

[0087] In one embodiment of the present disclosure, when the total number of substituents that the basic compound may have is set to T1 and the number of specific substituents among these substituents is set to T2, the content T% of the specific substituent may be defined as T2 / T1×100=T%.

[0088] In other words, in one example, The deuterium content of phenyl represented as 20% may mean that the total number of substituents that the phenyl may have is 5 (T1 in the formula), and the number of deuterium atoms in these substituents is 1 (T2 in the formula). In other words, a deuterium content of 20% in a phenyl group may be represented by the following structural formula.

[0089]

[0090] In addition, in one embodiment of the present disclosure, “phenyl group having a deuterium content of 0%” may mean a phenyl group not including a deuterium atom, that is, a phenyl group having 5 hydrogen atoms.

[0091] In the present disclosure, a C6-C60 aromatic hydrocarbon ring refers to a compound containing an aromatic ring formed by C6-C60 carbon and hydrogen. Examples thereof may include benzene, biphenyl, terphenyl, triphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, azulene, etc., but are not limited thereto, and may include all aromatic hydrocarbon ring compounds known in the art that satisfy the above carbon number.

[0092] One embodiment of the present application provides a heterocyclic compound represented by the following Chemical Formula 1.

[0093] [Chemical formula 1]

[0094]

[0095] In Chemical Formula 1,

[0096] A1 to A4 and B1 to B6 are the same as or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1-C60 alkyl; substituted or unsubstituted C2-C60 alkenyl; substituted or unsubstituted C2-C60 alkynyl; substituted or unsubstituted C1-C60 alkoxy; substituted or unsubstituted C3-C60 cycloalkyl; substituted or unsubstituted C2-C60 heterocycloalkyl; substituted or unsubstituted C6-C60 aryl; substituted or unsubstituted C2-C60 heteroaryl; and a group represented by the following Chemical Formula 2, and at least one of A1 to A4 and B1 to B4 is represented by the following Chemical Formula 2, and

[0097] When any one of A1 to A4 is a group represented by the following Chemical Formula 2, any one of B1 to B4 is represented by a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group, or

[0098] When any one of B1 to B4 is a group represented by the following Chemical Formula 2, any one of A1 to A4 is represented by a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group,

[0099] [Chemical formula 2]

[0100]

[0101] In chemical formula 2,

[0102] Ar1 and Ar2 are the same as or different from each other and are each independently a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group,

[0103] L1 to L3 are the same as or different from each other and are each independently a single bond; a substituted or unsubstituted C6-C60 arylene group; or a substituted or unsubstituted C2-C60 heteroarylene group,

[0104] m1 and m2 are integers from 0 to 5, and

[0105] n1 to n3 are the same as or different from each other, and are each independently an integer of 0 to 4.

[0106] In one embodiment of the present application, A1 to A4 and B1 to B6 are the same as or different from each other, and are each independently selected from hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1-C40 alkyl; substituted or unsubstituted C2-C40 alkenyl; substituted or unsubstituted C2-C40 alkynyl; substituted or unsubstituted C1-C40 alkoxy; substituted or unsubstituted C3-C40 cycloalkyl; substituted or unsubstituted C2-C40 heterocycloalkyl; substituted or unsubstituted C6-C40 aryl; substituted or unsubstituted C2-C40 heteroaryl; and a group consisting of a group represented by Chemical Formula 2, and at least one of A1 to A4 and B1 to B4 is represented by Chemical Formula 2. When any one of A1 to A4 is a group represented by Chemical Formula 2, any one of B1 to B4 may be represented by a substituted or unsubstituted C6-C40 aryl group; or a substituted or unsubstituted C2-C40 heteroaryl group, or when any one of B1 to B4 is a group represented by Chemical Formula 2, any one of A1 to A4 may be represented by a substituted or unsubstituted C6-C40 aryl group; or a substituted or unsubstituted C2-C40 heteroaryl group.

[0107] In one embodiment of the present application, A1 to A4 and B1 to B6 are the same as or different from each other, and are each independently selected from hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1-C30 alkyl; substituted or unsubstituted C2-C30 alkenyl; substituted or unsubstituted C2-C30 alkynyl; substituted or unsubstituted C1-C30 alkoxy; substituted or unsubstituted C3-C30 cycloalkyl; substituted or unsubstituted C2-C30 heterocycloalkyl; substituted or unsubstituted C6-C30 aryl; substituted or unsubstituted C2-C30 heteroaryl; and a group consisting of a group represented by Chemical Formula 2, and at least one of A1 to A4 and B1 to B4 is represented by Chemical Formula 2. When any one of A1 to A4 is a group represented by Chemical Formula 2, any one of B1 to B4 may be represented by a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C2-C30 heteroaryl group, or when any one of B1 to B4 is a group represented by Chemical Formula 2, any one of A1 to A4 may be represented by a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C2-C30 heteroaryl group.

[0108] In one embodiment of the present application, A1 to A4 and B1 to B6 are the same as or different from each other, and are each independently selected from hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1-C20 alkyl; substituted or unsubstituted C2-C20 alkenyl; substituted or unsubstituted C2-C20 alkynyl; substituted or unsubstituted C1-C20 alkoxy; substituted or unsubstituted C3-C20 cycloalkyl; substituted or unsubstituted C2-C20 heterocycloalkyl; substituted or unsubstituted C6-C20 aryl; substituted or unsubstituted C2-C20 heteroaryl; and the group consisting of the groups represented by Chemical Formula 2, and at least one of A1 to A4 and B1 to B4 is represented by Chemical Formula 2. When any one of A1 to A4 is a group represented by Chemical Formula 2, any one of B1 to B4 may be represented by a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group, or when any one of B1 to B4 is a group represented by Chemical Formula 2, any one of A1 to A4 may be represented by a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group.

[0109] In one embodiment of the present application, A1 to A4 and B1 to B6 are the same as or different from each other, and are each independently selected from hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1-C10 alkyl; substituted or unsubstituted C2-C10 alkenyl; substituted or unsubstituted C2-C10 alkynyl; substituted or unsubstituted C1-C10 alkoxy; substituted or unsubstituted C3-C10 cycloalkyl; substituted or unsubstituted C2-C10 heterocycloalkyl; substituted or unsubstituted C6-C10 aryl; substituted or unsubstituted C2-C10 heteroaryl; and a group consisting of a group represented by Chemical Formula 2, and at least one of A1 to A4 and B1 to B4 is represented by Chemical Formula 2. When any one of A1 to A4 is a group represented by Chemical Formula 2, any one of B1 to B4 may be represented by a substituted or unsubstituted C6-C10 aryl group; or a substituted or unsubstituted C2-C10 heteroaryl group, or when any one of B1 to B4 is a group represented by Chemical Formula 2, any one of A1 to A4 may be represented by a substituted or unsubstituted C6-C10 aryl group; or a substituted or unsubstituted C2-C10 heteroaryl group.

[0110] In one embodiment of the present application, A1 of Chemical Formula 1 is a group represented by Chemical Formula 2, and A2 to A4 are the same or different from each other and may be hydrogen or deuterium. Here, any one of B1 to B4 of Chemical Formula 1 may be represented by a substituted or unsubstituted C6-C20 aryl group or a substituted or unsubstituted C2-C20 heteroaryl group, and the group not represented by a substituted or unsubstituted C6-C20 aryl group or a substituted or unsubstituted C2-C20 heteroaryl group among B1 to B4, B5 and B6 may be hydrogen or deuterium.

[0111] In one embodiment of the present application, A2 of Chemical Formula 1 is a group represented by Chemical Formula 2, and A1, A3, and A4 are the same or different from each other and may be independently hydrogen or deuterium. Here, any one of B1 to B4 of Chemical Formula 1 may be represented by a substituted or unsubstituted C6-C20 aryl group or a substituted or unsubstituted C2-C20 heteroaryl group, and the group not represented by a substituted or unsubstituted C6-C20 aryl group or a substituted or unsubstituted C2-C20 heteroaryl group among B1 to B4, B5, and B6 may be independently hydrogen or deuterium.

[0112] In one embodiment of the present application, A3 of Chemical Formula 1 is a group represented by Chemical Formula 2, and A1, A2, and A4 are the same or different from each other and may be independently hydrogen or deuterium. Here, any one of B1 to B4 of Chemical Formula 1 may be represented by a substituted or unsubstituted C6-C20 aryl group or a substituted or unsubstituted C2-C20 heteroaryl group, and the group not represented by a substituted or unsubstituted C6-C20 aryl group or a substituted or unsubstituted C2-C20 heteroaryl group among B1 to B4, B5, and B6 may be independently hydrogen or deuterium.

[0113] In one embodiment of the present application, A4 of Chemical Formula 1 is a group represented by Chemical Formula 2, and A1 to A3 are the same or different from each other and can be independently hydrogen or deuterium. Here, any one of B1 to B4 of Chemical Formula 1 can be represented by a substituted or unsubstituted C6-C20 aryl group or a substituted or unsubstituted C2-C20 heteroaryl group, and the group not represented by a substituted or unsubstituted C6-C20 aryl group or a substituted or unsubstituted C2-C20 heteroaryl group among B1 to B4, B5 and B6 can be independently hydrogen or deuterium.

[0114] In one embodiment of the present application, A1 of Chemical Formula 1 is a group shown in Chemical Formula 2, and A2 to A4 are the same or different from each other and can be hydrogen or deuterium. Here, any one of B1 to B4 of Chemical Formula 1 can 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 dibenzofuranyl group; or a substituted or unsubstituted dibenzothienyl group, and the group not represented by substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted dibenzothienyl group in B1 to B4, B5 and B6 can be hydrogen or deuterium.

[0115] In one embodiment of the present application, A2 of Chemical Formula 1 is a group represented by Chemical Formula 2, and A1, A3, and A4 are the same or different from each other and may be hydrogen or deuterium. Here, any one of B1 to B4 of Chemical Formula 1 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 dibenzofuranyl group; or a substituted or unsubstituted dibenzothienyl group, and the group not represented by substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted dibenzothienyl group, B5, and B6 in B1 to B4 may be hydrogen or deuterium.

[0116] In one embodiment of the present application, A3 of Chemical Formula 1 is a group represented by Chemical Formula 2, and A1, A2, and A4 are the same or different from each other and may be independently hydrogen or deuterium. Here, any one of B1 to B4 of Chemical Formula 1 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 dibenzofuranyl group; or a substituted or unsubstituted dibenzothienyl group, and the group not represented by substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted dibenzothienyl group among B1 to B4, B5, and B6 may be independently hydrogen or deuterium.

[0117] In one embodiment of the present application, A4 of Chemical Formula 1 is a group represented by Chemical Formula 2, and A1 to A3 are the same or different from each other and can be hydrogen or deuterium. Here, any one of B1 to B4 of Chemical Formula 1 can 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 dibenzofuranyl group; or a substituted or unsubstituted dibenzothienyl group, and the group not represented by substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted dibenzothienyl group in B1 to B4, B5 and B6 can be hydrogen or deuterium.

[0118] In one embodiment of the present application, B1 of Chemical Formula 1 is a group represented by Chemical Formula 2, and B2 to B6 are the same or different from each other and can be independently hydrogen or deuterium. Here, any one of A1 to A4 of Chemical Formula 1 can be represented by a substituted or unsubstituted C6-C20 aryl group or a substituted or unsubstituted C2-C20 heteroaryl group.

[0119] In one embodiment of the present application, B2 of Chemical Formula 1 is a group represented by Chemical Formula 2, and B1, B3 to B6 are the same as or different from each other and can be independently hydrogen or deuterium. Here, any one of A1 to A4 of Chemical Formula 1 can be represented by a substituted or unsubstituted C6-C20 aryl group or a substituted or unsubstituted C2-C20 heteroaryl group.

[0120] In one embodiment of the present application, B3 of Chemical Formula 1 is a group represented by Chemical Formula 2, and B1, B2, B4 to B6 are the same as or different from each other and can be independently hydrogen or deuterium. Here, any one of A1 to A4 of Chemical Formula 1 can be represented by a substituted or unsubstituted C6-C20 aryl group or a substituted or unsubstituted C2-C20 heteroaryl group.

[0121] In one embodiment of the present application, B4 of Chemical Formula 1 is a group represented by Chemical Formula 2, and B1 to B3, B5 and B6 are the same or different from each other and can be independently hydrogen or deuterium. Here, any one of A1 to A4 of Chemical Formula 1 can be represented by a substituted or unsubstituted C6-C20 aryl group or a substituted or unsubstituted C2-C20 heteroaryl group.

[0122] In one embodiment of the present application, B1 of Chemical Formula 1 is a group represented by Chemical Formula 2, and B2 to B6 are the same or different from each other and can be independently hydrogen or deuterium. Here, any one of A1 to A4 of Chemical Formula 1 can 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 dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophene group.

[0123] In one embodiment of the present application, B2 of Chemical Formula 1 is a group represented by Chemical Formula 2, and B1, B3 to B6 are the same or different from each other and can be independently hydrogen or deuterium. Here, any one of A1 to A4 of Chemical Formula 1 can 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 dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophene group.

[0124] In one embodiment of the present application, B3 of Chemical Formula 1 is a group represented by Chemical Formula 2, and B1, B2, B4 to B6 are the same or different from each other and can be independently hydrogen or deuterium. Here, any one of A1 to A4 of Chemical Formula 1 can 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 dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group.

[0125] In one embodiment of the present application, B4 of Chemical Formula 1 is a group represented by Chemical Formula 2, and B1 to B3, B5 and B6 are the same or different from each other and can be independently hydrogen or deuterium. Here, any one of A1 to A4 of Chemical Formula 1 can 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 dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophene group.

[0126] In one embodiment of the present application, Ar1 and Ar2 in Chemical Formula 2 are the same as or different from each other, and may be each independently a substituted or unsubstituted C6-C40 aryl group; or a substituted or unsubstituted C2-C40 heteroaryl group.

[0127] In one embodiment of the present application, Ar1 and Ar2 in Chemical Formula 2 are the same as or different from each other, and may be each independently a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C2-C30 heteroaryl group.

[0128] In one embodiment of the present application, Ar1 and Ar2 in Chemical Formula 2 are the same as or different from each other, and may be each independently a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group.

[0129] In one embodiment of the present application, Ar1 and Ar2 in Chemical Formula 2 are the same as or different from each other, and may be independently a substituted or unsubstituted C6-C10 aryl group; or a substituted or unsubstituted C2-C10 heteroaryl group.

[0130] In one embodiment of the present application, Ar1 and Ar2 of Chemical Formula 2 are the same as or different from each other, and may be each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted 9,9-dimethylfluorenyl group; a substituted or unsubstituted anthracenyl group; a substituted or unsubstituted pyrene group; a substituted or unsubstituted chrysene group; a substituted or unsubstituted fluoranthene group; a substituted or unsubstituted 9,9-diphenylfluorenyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted dibenzothiophenyl group; a substituted or unsubstituted spirobifluorenyl group; or a substituted or unsubstituted triphenylene group.

[0131] In one embodiment of the present application, L1 to L3 of Chemical Formula 2 are the same as or different from each other, and may each independently be a single bond; a substituted or unsubstituted C6-C40 arylene group; or a substituted or unsubstituted C2-C40 heteroarylene group.

[0132] In one embodiment of the present application, L1 to L3 of Chemical Formula 2 may be the same as or different from each other, and may each independently be a single bond; a substituted or unsubstituted C6-C30 arylene group; or a substituted or unsubstituted C2-C30 heteroarylene group.

[0133] In one embodiment of the present application, L1 to L3 of Chemical Formula 2 may be the same as or different from each other, and may each independently be a single bond; a substituted or unsubstituted C6-C20 arylene group; or a substituted or unsubstituted C2-C20 heteroarylene group.

[0134] In one embodiment of the present application, L1 to L3 of Chemical Formula 2 may be the same as or different from each other, and may each independently be a single bond; a substituted or unsubstituted C6-C10 arylene group; or a substituted or unsubstituted C2-C10 heteroarylene group.

[0135] In one embodiment of the present application, L1 to L3 of Chemical Formula 2 may be the same as or different from each other, and may each independently be a single bond; a substituted or unsubstituted phenylene; a substituted or unsubstituted biphenylene; a substituted or unsubstituted terphenylene; a substituted or unsubstituted naphthylene; a substituted or unsubstituted dibenzofuranylene; a substituted or unsubstituted dibenzothiophenylene; or a substituted or unsubstituted carbazolylene.

[0136] In one embodiment of the present application, Chemical Formula 1 may be represented by any one of the following Chemical Formulas 1-1 to 1-8.

[0137] [Chemical formula 1-1]

[0138]

[0139] [Chemical formula 1-2]

[0140]

[0141] [Chemical formula 1-3]

[0142]

[0143] [Chemical formula 1-4]

[0144]

[0145] [Chemical formula 1-5]

[0146]

[0147] [Chemical formula 1-6]

[0148]

[0149] [Chemical formula 1-7]

[0150]

[0151] [Chemical formula 1-8]

[0152]

[0153] In Chemical Formulas 1-1 to 1-8,

[0154] A1 to A4, B1 to B6, Ar1, Ar2, L1 to L3, m1, m2, n1 to n3 have the same definitions as in Chemical Formula 1,

[0155] At least one of B1 to B4 in Chemical Formulae 1-1 to 1-4 may be represented by a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group, and

[0156] At least one of A1 to A4 in Chemical Formulae 1-5 to 1-8 may be represented by a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group.

[0157] In one embodiment of the present application, at least one of B1 to B4 in Chemical Formulae 1-1 to 1-4 may be a substituted or unsubstituted C6-C40 aryl group; or a substituted or unsubstituted C2-C40 heteroaryl group.

[0158] In one embodiment of the present application, at least one of B1 to B4 in Chemical Formulae 1-1 to 1-4 may be a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C2-C30 heteroaryl group.

[0159] In one embodiment of the present application, at least one of B1 to B4 in Chemical Formulae 1-1 to 1-4 may be a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group.

[0160] In one embodiment of the present application, at least one of B1 to B4 in Chemical Formulae 1-1 to 1-4 may be a substituted or unsubstituted C6-C10 aryl group; or a substituted or unsubstituted C2-C10 heteroaryl group.

[0161] In one embodiment of the present application, B1 in Chemical Formula 1-1 is 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 dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group, and A2 to A4 and B2 to B6 are the same as or different from each other, and may each independently be hydrogen; or deuterium.

[0162] In one embodiment of the present application, B2 in Chemical Formula 1-1 is 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 dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group, and A2 to A4, B1, B3 to B6 are the same as or different from each other, and may each independently be hydrogen; or deuterium.

[0163] In one embodiment of the present application, B3 in Chemical Formula 1-1 is 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 dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group, and A2 to A4, B1, B2, B4 to B6 are the same as or different from each other, and may each independently be hydrogen; or deuterium.

[0164] In one embodiment of the present application, B4 in Chemical Formula 1-1 is 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 dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group, and A2 to A4, B1 to B3, B5 and B6 are the same as or different from each other, and may each independently be hydrogen; or deuterium.

[0165] In one embodiment of the present application, B1 in Chemical Formula 1-2 is 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 dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group, and A1, A3, A4, B2 to B6 are the same as or different from each other and may each independently be hydrogen; or deuterium.

[0166] In one embodiment of the present application, B2 in Chemical Formula 1-2 is 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 dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group, and A1, A3, A4, B1, B3 to B6 are the same as or different from each other and may each independently be hydrogen; or deuterium.

[0167] In one embodiment of the present application, B3 in Chemical Formula 1-2 is 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 dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group, and A1, A3, A4, B1, B2, B4 to B6 are the same as or different from each other and may each independently be hydrogen; or deuterium.

[0168] In one embodiment of the present application, B4 in Chemical Formula 1-2 is 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 dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group, and A1, A3, A4, B1 to B3, B5 and B6 are the same as or different from each other, and may each independently be hydrogen; or deuterium.

[0169] In one embodiment of the present application, B1 in Chemical Formulas 1-3 is 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 dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group, and A1, A2, A4, B2 to B6 are the same as or different from each other and may each independently be hydrogen; or deuterium.

[0170] In one embodiment of the present application, B2 in Chemical Formulas 1-3 is 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 dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group, and A1, A2, A4, B1, B3 to B6 are the same as or different from each other and may each independently be hydrogen; or deuterium.

[0171] In one embodiment of the present application, B3 in Chemical Formula 1-3 is 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 dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group, and A1, A2, A4, B1, B2, B4 to B6 are the same as or different from each other and may each independently be hydrogen; or deuterium.

[0172] In one embodiment of the present application, B4 in Chemical Formula 1-3 is 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 dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group, and A1, A2, A4, B1 to B3, B5 and B6 are the same as or different from each other, and may each independently be hydrogen; or deuterium.

[0173] In one embodiment of the present application, B1 in Chemical Formulas 1-4 is 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 dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group, and A1 to A3 and B2 to B6 are the same as or different from each other, and may each independently be hydrogen; or deuterium.

[0174] In one embodiment of the present application, B2 in Chemical Formulas 1-4 is 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 dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group, and A1 to A3, B1, B3 to B6 are the same as or different from each other and may each independently be hydrogen; or deuterium.

[0175] In one embodiment of the present application, B3 in Chemical Formulas 1-4 is 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 dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group, and A1 to A3, B1, B2, B4 to B6 are the same as or different from each other and may each independently be hydrogen; or deuterium.

[0176] In one embodiment of the present application, B4 in Chemical Formulas 1-4 is 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 dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group, and A1 to A3, B1 to B3, B5 and B6 are the same as or different from each other, and may each independently be hydrogen; or deuterium.

[0177] In one embodiment of the present application, at least one of A1 to A4 in Chemical Formulae 1-5 to 1-8 may be a substituted or unsubstituted C6-C40 aryl group; or a substituted or unsubstituted C2-C40 heteroaryl group.

[0178] In one embodiment of the present application, at least one of A1 to A4 in Chemical Formulae 1-5 to 1-8 may be a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C2-C30 heteroaryl group.

[0179] In one embodiment of the present application, at least one of A1 to A4 in Chemical Formulae 1-5 to 1-8 may be a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group.

[0180] In one embodiment of the present application, at least one of A1 to A4 in Chemical Formulae 1-5 to 1-8 may be a substituted or unsubstituted C6-C10 aryl group; or a substituted or unsubstituted C2-C10 heteroaryl group.

[0181] In one embodiment of the present application, A1 in Chemical Formulas 1-5 is 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 dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group, and A2 to A4 and B2 to B6 are the same as or different from each other, and may each independently be hydrogen; or deuterium.

[0182] In one embodiment of the present application, A2 in Chemical Formulas 1-5 is 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 dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group, and A1, A3, A4, B2 to B6 are the same as or different from each other and may each independently be hydrogen; or deuterium.

[0183] In one embodiment of the present application, A3 in Chemical Formulas 1-5 is 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 dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group, and A1, A2, A4, B2 to B6 are the same as or different from each other and may each independently be hydrogen; or deuterium.

[0184] In one embodiment of the present application, A4 in Chemical Formulas 1-5 is 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 dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group, and A1 to A3 and B2 to B6 are the same or different from each other, and may each independently be hydrogen; or deuterium.

[0185] In one embodiment of the present application, A1 in Chemical Formulas 1-6 is 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 dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group, and A2 to A4, B1, B3 to B6 are the same as or different from each other, and may each independently be hydrogen; or deuterium.

[0186] In one embodiment of the present application, A2 in Chemical Formulas 1-6 is 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 dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group, and A1, A3, A4, B1, B3 to B6 are the same as or different from each other and may each independently be hydrogen; or deuterium.

[0187] In one embodiment of the present application, A3 in Chemical Formulas 1-6 is 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 dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group, and A1, A2, A4, B1, B3 to B6 are the same as or different from each other and may each independently be hydrogen; or deuterium.

[0188] In one embodiment of the present application, A4 in Chemical Formulas 1-6 is 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 dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group, and A1 to A3, B1, B3 to B6 are the same as or different from each other and may each independently be hydrogen; or deuterium.

[0189] In one embodiment of the present application, A1 in Chemical Formulas 1-7 is 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 dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group, and A2 to A4, B1, B2, B4 to B6 are the same as or different from each other, and may each independently be hydrogen; or deuterium.

[0190] In one embodiment of the present application, A2 in Chemical Formulas 1-7 is 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 dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group, and A1, A3, A4, B1, B2, B4 to B6 are the same as or different from each other and may each independently be hydrogen; or deuterium.

[0191] In one embodiment of the present application, A3 in Chemical Formulas 1-7 is 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 dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group, and A1, A2, A4, B1, B2, B4 to B6 are the same as or different from each other and may each independently be hydrogen; or deuterium.

[0192] In one embodiment of the present application, A4 in Chemical Formulas 1-7 is 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 dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group, and A1 to A3, B1, B2, B4 to B6 are the same as or different from each other and may each independently be hydrogen; or deuterium.

[0193] In one embodiment of the present application, A1 in Chemical Formulas 1-8 is 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 dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group, and A2 to A4, B1 to B3, B5 and B6 are the same as or different from each other, and may each independently be hydrogen; or deuterium.

[0194] In one embodiment of the present application, A2 in Chemical Formulas 1-8 is 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 dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group, and A1, A3, A4, B1 to B3, B5 and B6 are the same as or different from each other, and may each independently be hydrogen; or deuterium.

[0195] In one embodiment of the present application, A3 in Chemical Formulas 1-8 is 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 dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group, and A1, A2, A4, B1 to B3, B5 and B6 are the same as or different from each other, and may each independently be hydrogen; or deuterium.

[0196] In one embodiment of the present application, A4 in Chemical Formulas 1-8 is 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 dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group, and A1 to A3, B1 to B3, B5 and B6 are the same as or different from each other, and may each independently be hydrogen; or deuterium.

[0197] In one embodiment of the present application, Ar1 and Ar2 of Chemical Formula 2 may be represented by any one of the following Chemical Formulas 3 and 4:

[0198] [Chemical formula 3]

[0199]

[0200] [Chemical formula 4]

[0201]

[0202] In Chemical Formula 3 and Chemical Formula 4,

[0203] X1 is O, S or CRaRb,

[0204] Ar3 is a substituted or unsubstituted C6-C60 aryl group,

[0205] R1, R2, Ra and Rb are the same as or different from each other and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1-C60 alkyl; substituted or unsubstituted C2-C60 alkenyl; substituted or unsubstituted C2-C60 alkynyl; substituted or unsubstituted C1-C60 alkoxy; substituted or unsubstituted C3-C60 cycloalkyl; substituted or unsubstituted C2-C60 heterocycloalkyl; substituted or unsubstituted C6-C60 aryl; and substituted or unsubstituted C2-C60 heteroaryl, or two or more groups adjacent to each other may be bonded to each other to form a substituted or unsubstituted C6-C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2-C60 heterocyclic ring,

[0206] n4 is an integer from 0 to 4, and

[0207] n5 is an integer from 0 to 3.

[0208] In one embodiment of the present application, X1 of Chemical Formula 3 may be O.

[0209] In one embodiment of the present application, X1 of Chemical Formula 3 may be S.

[0210] In one embodiment of the present application, X1 of Chemical Formula 3 may be CRaRb.

[0211] In one embodiment of the present application, Ar3 of Chemical Formula 4 may be a substituted or unsubstituted C6-C40 aryl group.

[0212] In one embodiment of the present application, Ar3 of Chemical Formula 4 may be a substituted or unsubstituted C6-C30 aryl group.

[0213] In one embodiment of the present application, Ar3 of Chemical Formula 4 may be a substituted or unsubstituted C6-C20 aryl group.

[0214] In one embodiment of the present application, Ar3 of Chemical Formula 4 may be a substituted or unsubstituted C6-C10 aryl group.

[0215] In one embodiment of the present application, Ar3 of Chemical Formula 4 can 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 naphthyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted 9,9-dimethylfluorenyl group; a substituted or unsubstituted anthracene group; a substituted or unsubstituted pyrene group; a substituted or unsubstituted chrysene group; a substituted or unsubstituted fluoranthene group; a substituted or unsubstituted 9,9-diphenylfluorenyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted spirobifluorenyl group; or a substituted or unsubstituted triphenylene group.

[0216] In one embodiment of the present application, Ar3 of Chemical Formula 4 may be each independently a phenyl group; a biphenyl group; a terphenyl group; a naphthyl group; a fluorenyl group; a 9,9-dimethylfluorenyl group; a 9,9-diphenylfluorenyl group; or a spirobifluorenyl group.

[0217] In one embodiment of the present application, R1, R2, Ra and Rb are the same as or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1-C40 alkyl; substituted or unsubstituted C2-C40 alkenyl; substituted or unsubstituted C2-C40 alkynyl; substituted or unsubstituted C1-C40 alkoxy; substituted or unsubstituted C3-C40 cycloalkyl; substituted or unsubstituted C2-C40 heterocycloalkyl; substituted or unsubstituted C6-C40 aryl; and substituted or unsubstituted C2-C40 heteroaryl, or two or more groups adjacent to each other may be bonded to each other to form a substituted or unsubstituted C6-C40 aromatic hydrocarbon ring or a substituted or unsubstituted C2-C40 heterocycle.

[0218] In one embodiment of the present application, R1, R2, Ra and Rb are the same as or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1-C30 alkyl; substituted or unsubstituted C2-C30 alkenyl; substituted or unsubstituted C2-C30 alkynyl; substituted or unsubstituted C1-C30 alkoxy; substituted or unsubstituted C3-C30 cycloalkyl; substituted or unsubstituted C2-C30 heterocycloalkyl; substituted or unsubstituted C6-C30 aryl; and substituted or unsubstituted C2-C30 heteroaryl, or two or more groups adjacent to each other may be bonded to each other to form a substituted or unsubstituted C6-C30 aromatic hydrocarbon ring or a substituted or unsubstituted C2-C30 heterocycle.

[0219] In one embodiment of the present application, R1, R2, Ra and Rb are the same as or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1-C20 alkyl; substituted or unsubstituted C2-C20 alkenyl; substituted or unsubstituted C2-C20 alkynyl; substituted or unsubstituted C1-C20 alkoxy; substituted or unsubstituted C3-C20 cycloalkyl; substituted or unsubstituted C2-C20 heterocycloalkyl; substituted or unsubstituted C6-C20 aryl; and substituted or unsubstituted C2-C20 heteroaryl, or two or more groups adjacent to each other may be bonded to each other to form a substituted or unsubstituted C6-C20 aromatic hydrocarbon ring or a substituted or unsubstituted C2-C20 heterocycle.

[0220] In one embodiment of the present application, R1, R2, Ra and Rb are the same as or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1-C10 alkyl; substituted or unsubstituted C2-C10 alkenyl; substituted or unsubstituted C2-C10 alkynyl; substituted or unsubstituted C1-C10 alkoxy; substituted or unsubstituted C3-C10 cycloalkyl; substituted or unsubstituted C2-C10 heterocycloalkyl; substituted or unsubstituted C6-C10 aryl; and substituted or unsubstituted C2-C10 heteroaryl, or two or more groups adjacent to each other may be bonded to each other to form a substituted or unsubstituted C6-C10 aromatic hydrocarbon ring or a substituted or unsubstituted C2-C10 heterocycle.

[0221] In one embodiment of the present application, R1, R2, Ra and Rb are the same as or different from each other, and are each independently hydrogen; deuterium; substituted or unsubstituted methyl; substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted terphenyl; or two or more substituted or unsubstituted phenyl groups adjacent to each other may be bonded to each other to form a substituted or unsubstituted spirobifluorenyl.

[0222] In one embodiment of the present application, the heterocyclic compound represented by Chemical Formula 1 may not include deuterium as a substituent, or may have a deuterium content of, for example, 0% or more, 1% or more, 5% or more, 10% or more, 15% or more, 20% or more, 25% or more, 30% or more, 35% or more, 40% or more, 45% or more, or 50% or more, and 100% or less, 95% or less, 90% or less, 85% or less, 80% or less, 75% or less, 70% or less, 65% or less, or 60% or less, based on the total number of hydrogen atoms and deuterium atoms.

[0223] In one embodiment of the present application, the heterocyclic compound represented by Chemical Formula 1 may not contain deuterium, or may have a deuterium content of 1% to 100% based on the total number of hydrogen atoms and deuterium atoms.

[0224] In one embodiment of the present application, the heterocyclic compound represented by Chemical Formula 1 may not contain deuterium, or may have a deuterium content of 10% to 100% based on the total number of hydrogen atoms and deuterium atoms.

[0225] In one embodiment of the present application, the heterocyclic compound represented by Chemical Formula 1 may not contain deuterium, or may have a deuterium content of 20% to 90% based on the total number of hydrogen atoms and deuterium atoms.

[0226] In one embodiment of the present application, the heterocyclic compound represented by Chemical Formula 1 may not contain deuterium, or may have a deuterium content of 30% to 80% based on the total number of hydrogen atoms and deuterium atoms.

[0227] In one embodiment of the present application, the heterocyclic compound represented by Chemical Formula 1 may not contain deuterium, or may have a deuterium content of 40% to 70% based on the total number of hydrogen atoms and deuterium atoms.

[0228] In one embodiment of the present application, the heterocyclic compound represented by Chemical Formula 1 may not contain deuterium, or may have a deuterium content of 50% to 60% based on the total number of hydrogen atoms and deuterium atoms.

[0229] One embodiment of the present application provides a heterocyclic compound, wherein Chemical Formula 1 is represented by any one of the following compounds. In addition, in one embodiment of the present application, the following compound is only an example, and the present application is not limited thereto, and may include other compounds included in Chemical Formula 1 that include additional substituents.

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242] In addition, by introducing various substituents into the structure of Chemical Formula 1, compounds having unique properties of the introduced substituents can be synthesized. For example, by introducing substituents of hole injection layer materials, hole transport layer materials, light emitting layer materials, electron transport layer materials, and charge generation layer materials commonly used in manufacturing organic light emitting devices into the core structure, materials that meet the required conditions for each organic material layer can be synthesized.

[0243] Furthermore, by introducing various substituents into the structure of Chemical Formula 1, the energy band gap can be finely controlled, while the properties at the interface between organic materials can be enhanced, and material applications can become diversified.

[0244] Another embodiment of the present disclosure provides an organic light emitting device including the heterocyclic compound represented by Chemical Formula 1. “Organic light emitting device” may be expressed by terms such as “organic light emitting diode”, “OLED”, “OLED device”, and “organic electroluminescent device”.

[0245] One embodiment of the present application provides an organic light-emitting device, comprising: a first electrode; a second electrode arranged opposite to the first electrode; and one or more organic material layers arranged between the first electrode and the second electrode, wherein one or more layers of the organic material layer include a heterocyclic compound represented by Chemical Formula 1.

[0246] In one embodiment of the present application, the first electrode may be a positive electrode, and the second electrode may be a negative electrode.

[0247] In another embodiment, the first electrode may be a cathode and the second electrode may be an anode.

[0248] In one embodiment of the present application, the organic light emitting device may be a blue organic light emitting device, and the heterocyclic compound according to Chemical Formula 1 may be used as a material of the blue organic light emitting device.

[0249] In one embodiment of the present application, the organic light emitting device may be a green organic light emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material of the green organic light emitting device.

[0250] In one embodiment of the present application, the organic light emitting device may be a red organic light emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material of the red organic light emitting device.

[0251] In one embodiment of the present application, the organic light emitting device may be a blue organic light emitting device, and the heterocyclic compound according to Chemical Formula 1 may be used as a light emitting layer material of the blue organic light emitting device.

[0252] In one embodiment of the present application, the organic light emitting device may be a green organic light emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a light emitting layer material of the green organic light emitting device.

[0253] In one embodiment of the present application, the organic light emitting device may be a red organic light emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a light emitting layer material of the red organic light emitting device.

[0254] The detailed description about the heterocyclic compound represented by Chemical Formula 1 is the same as the description provided above.

[0255] In addition to using the above-mentioned heterocyclic compound to form one or more organic material layers, the organic light-emitting device of the present disclosure may be manufactured using common organic light-emitting device manufacturing methods and materials.

[0256] When manufacturing an organic light-emitting device, a solution coating method and a vacuum deposition method can be used to form a heterocyclic compound into an organic material layer. Here, the solution coating method means spin coating, dip coating, inkjet printing, screen printing, spray coating, roller coating, etc., but is not limited thereto.

[0257] The organic material layer of the organic light-emitting device of the present disclosure may be formed as a single-layer structure, but may also be formed as a multilayer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present disclosure may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as organic material layers. However, the structure of the organic light-emitting device is not limited thereto, and may include a smaller number of organic material layers.

[0258] The heterocyclic compound can be used as a light-emitting material alone or in a mixture with an N-type host, and can be used as a host material or a dopant material of a light-emitting layer.

[0259] In particular, the heterocyclic compound represented by Chemical Formula 1 has a naphtho[2,1-b]benzofuran functional group. The structure of naphtho[2,1-b]benzofuran functional group has a high glass transition temperature. Therefore, due to the high thermal stability in the molecule, the life characteristics of the organic light-emitting device can be enhanced.

[0260] When naphtho[2,1-b]benzofuran is used alone, a planar structure of the molecule develops and the molecule is easy to crystallize. When a material that is easy to crystallize is used in an organic light-emitting device, the material crystallizes due to the Joule heat generated during the driving of the device, which reduces the life of the device. In the heterocyclic compound represented by Chemical Formula 1 according to the present disclosure, naphtho[2,1-b]benzofuran is not used alone, and naphtho[2,1-b]benzofuran is substituted by an aryl group (or a heteroaryl group) and an aromatic amine group represented by Chemical Formula 2 to distort the molecular structure, thereby preventing the molecule from crystallizing.

[0261] Furthermore, since the hole transport characteristics can be variously controlled by introducing various substituents in Ar1 or Ar2 of Chemical Formula 2, there is an advantageous effect of adjusting the charge balance even if any common layer is used in the organic light emitting device.

[0262] Therefore, when the compound represented by Chemical Formula 1 is used for an organic material layer, it is possible to reduce the driving voltage of an organic light-emitting device, improve its light-emitting efficiency, and enhance the lifespan characteristics of the organic light-emitting device by the thermal stability of the compound.

[0263] In the organic light emitting device of the present disclosure, the organic material layer includes a light emitting layer, and the light emitting layer may include the heterocyclic compound of Chemical Formula 1.

[0264] In the organic light-emitting device of the present disclosure, the organic material layer includes a light-emitting layer, and the light-emitting layer may include the heterocyclic compound of Chemical Formula 1 as a host of the light-emitting layer.

[0265] In another embodiment of the present disclosure, the organic light-emitting device may further include one or two or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron injection layer, an electron transport layer, an electron blocking layer and a hole blocking layer.

[0266] In one embodiment of the present disclosure, the organic light emitting device may include one or more organic material layers, the organic material layer may include a hole transport layer, and the hole transport layer may include the heterocyclic compound represented by Chemical Formula 1.

[0267] In one embodiment of the present disclosure, the organic light emitting device may include one or more organic material layers, the organic material layer may include a hole transport auxiliary layer, and the hole transport auxiliary layer may include the heterocyclic compound represented by Chemical Formula 1.

[0268] In one embodiment of the present disclosure, the organic light emitting device may include one or more organic material layers, the organic material layer may include an electron transport layer, and the electron transport layer may include the heterocyclic compound represented by Chemical Formula 1.

[0269] In one embodiment of the present disclosure, the organic light emitting device may include one or more organic material layers, the organic material layers may include an electron blocking layer, and the electron blocking layer may include the heterocyclic compound represented by Chemical Formula 1.

[0270] In one embodiment of the present disclosure, the organic material layer includes the heterocyclic compound represented by Chemical Formula 1, and a phosphorescent dopant may be used therewith.

[0271] As the 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, however, the scope of the present disclosure is not limited to these examples.

[0272] M can be iridium, platinum, osmium, etc.

[0273] L is through sp2 Carbon and heteroatoms are anionic bidentate ligands coordinated with M, and X can play a role in capturing electrons or holes. Non-limiting examples of L, L' and L" may include 2-(1-naphthyl)benzoxazole, 2-phenylbenzoxazole, 2-phenylbenzothiazole, 7,8-benzoquinoline, phenylpyridine, benzothienylpyridine, 3-methoxy-2-phenylpyridine, thienylpyridine, tolylpyridine, etc. Non-limiting examples of X' and X" may include acetylacetonate (acac), hexafluoroacetylacetonate, salicylidene, picolinate, 8-hydroxyquinolinate, etc.

[0274] Specific examples of the phosphorescent dopant are shown below, however, the phosphorescent dopant is not limited to these examples:

[0275]

[0276] In one embodiment of the present disclosure, the organic material layer includes the heterocyclic compound represented by Chemical Formula 1, and an iridium-based dopant may be used therewith.

[0277] In one embodiment of the present disclosure, as an iridium-based dopant, a red phosphorescent dopant (piq)2(Ir)(acac) may be used.

[0278] In one embodiment of the present disclosure, as the iridium-based dopant, a green phosphorescent dopant Ir(ppy) 3 may be used.

[0279] In one embodiment of the present disclosure, 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.

[0280] In the organic light emitting device according to one embodiment of the present disclosure, the organic material layer includes a hole transport layer or a hole transport auxiliary layer, and the hole transport layer or the hole transport auxiliary layer may include the heterocyclic compound represented by Chemical Formula 1.

[0281] In an organic light emitting device according to another embodiment of the present disclosure, the organic material layer includes an electron injection layer or an electron transport layer, and the electron injection layer or the electron transport layer may include the heterocyclic compound represented by Chemical Formula 1.

[0282] In an organic light emitting device according to another embodiment of the present disclosure, the organic material layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer may include the heterocyclic compound represented by Chemical Formula 1.

[0283] In an organic light emitting device according to another embodiment of the present disclosure, the organic material layer includes an electron transport layer, an emission layer or a hole blocking layer, and the electron transport layer, the emission layer or the hole blocking layer may include the heterocyclic compound represented by Chemical Formula 1.

[0284] In an organic light emitting device according to another embodiment of the present disclosure, the organic material layer includes a light emitting layer, and the light emitting layer may include the heterocyclic compound represented by Chemical Formula 1.

[0285] In an organic light emitting device according to another embodiment of the present disclosure, the organic material 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 Chemical Formula 1.

[0286] In an organic light emitting device according to another embodiment, the light emitting layer may include two or more host materials, and at least one of the host materials may include the heterocyclic compound represented by Chemical Formula 1.

[0287] In an organic light emitting device according to another embodiment, two or more host materials may be premixed and used in a light emitting layer, and at least one of the two or more host materials may include the heterocyclic compound represented by Chemical Formula 1.

[0288] Premixing means placing and mixing two or more host materials in one supply before depositing them on the layer of organic material.

[0289] In the organic light emitting device according to one embodiment of the present application, the organic material layer including the heterocyclic compound represented by Chemical Formula 1 further includes a heterocyclic compound represented by the following Chemical Formula 5.

[0290] [Chemical formula 5]

[0291]

[0292] In Chemical Formula 5,

[0293] Y1 to Y3 are the same as or different from each other, and are each independently CH or N, and at least one of Y1 to Y3 is N,

[0294] L3 to L6 are the same as or different from each other and are each independently a single bond; a substituted or unsubstituted C6-C60 arylene group; or a substituted or unsubstituted C2-C60 heteroarylene group,

[0295] Ar4 to Ar6 are the same as or different from each other, and are each independently a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group,

[0296] m3 to m5 are the same as or different from each other and are each independently an integer from 0 to 5,

[0297] n6 to n9 are the same as or different from each other and are each independently an integer from 0 to 4,

[0298] p is an integer of 0 or 1,

[0299] Ra and Rb are the same as or different from each other and are each hydrogen; or deuterium,

[0300] a is an integer from 0 to 4,

[0301] b is an integer from 0 to 6, and

[0302] When p is 0, b is an integer from 0 to 4.

[0303] When the heterocyclic compound of Chemical Formula 1 and the heterocyclic compound of Chemical Formula 5 are included in the organic material layer of the organic light emitting device, more excellent effects of efficiency and lifespan are obtained. According to this result, it can be expected that an exciplex phenomenon occurs when both compounds are included.

[0304] The image of the excited complex is a phenomenon in which energy having the magnitude of the highest occupied molecular orbital (HOMO) energy level of the donor (p-host) and the lowest unoccupied molecular orbital (LUMO) energy level of the acceptor (n-host) is released due to the exchange of electrons between two molecules. When the image of the excited complex occurs between two molecules, reverse intersystem crossing (RISC) occurs, as a result of which the internal quantum efficiency of fluorescence can be increased to 100%. When a donor (p-host) having good hole transport ability and an acceptor (n-host) having 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 that the driving voltage can be reduced, which helps to increase the life span.

[0305] In one embodiment of the present application, Y1 of Chemical Formula 5 is N, and Y2 and Y3 may be CH.

[0306] In another example, Y1 and Y2 of Chemical Formula 5 are N, and Y3 may be CH.

[0307] In another example, Y1 and Y3 of Chemical Formula 5 are N, and Y2 may be CH.

[0308] In another example, Y1 of Chemical Formula 5 is CH, and Y2 and Y3 may be N.

[0309] In another example, Y1 and Y2 of Chemical Formula 5 are CH, and Y3 may be N.

[0310] In another example, Y1 and Y3 of Chemical Formula 5 are CH, and Y2 may be N.

[0311] In another example, Y1 to Y3 of Chemical Formula 5 may be N.

[0312] In one embodiment of the present application, L3 to L6 of Chemical Formula 5 are the same as or different from each other, and may be each independently a single bond; a substituted or unsubstituted C6-C40 arylene group; or a substituted or unsubstituted C2-C40 heteroarylene group.

[0313] In one embodiment of the present application, L3 to L6 of Chemical Formula 5 are the same as or different from each other, and may be each independently a single bond; a substituted or unsubstituted C6-C30 arylene group; or a substituted or unsubstituted C2-C30 heteroarylene group.

[0314] In one embodiment of the present application, L3 to L6 of Chemical Formula 5 are the same as or different from each other, and may be each independently a single bond; a substituted or unsubstituted C6-C20 arylene group; or a substituted or unsubstituted C2-C20 heteroarylene group.

[0315] In one embodiment of the present application, L3 to L6 of Chemical Formula 5 are the same as or different from each other, and may be each independently a single bond; a substituted or unsubstituted C6-C10 arylene group; or a substituted or unsubstituted C2-C10 heteroarylene group.

[0316] In one embodiment of the present application, L3 to L6 of Chemical Formula 5 are the same as or different from each other, and may each independently be a single bond; a substituted or unsubstituted phenylene; a substituted or unsubstituted biphenylene; a substituted or unsubstituted terphenylene; a substituted or unsubstituted naphthylene; a substituted or unsubstituted dibenzofuranylene; or a substituted or unsubstituted dibenzothiophenylene.

[0317] In one embodiment of the present application, Ar4 to Ar6 of Chemical Formula 5 are the same as or different from each other, and may each independently be a substituted or unsubstituted C6-C40 aryl group; or a substituted or unsubstituted C2-C40 heteroaryl group.

[0318] In one embodiment of the present application, Ar4 to Ar6 of Chemical Formula 5 are the same as or different from each other, and may each independently be a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C2-C30 heteroaryl group.

[0319] In one embodiment of the present application, Ar4 to Ar6 of Chemical Formula 5 are the same as or different from each other, and may be each independently a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group.

[0320] In one embodiment of the present application, Ar4 to Ar6 of Chemical Formula 5 are the same as or different from each other, and may be each independently a substituted or unsubstituted C6-C10 aryl group; or a substituted or unsubstituted C2-C10 heteroaryl group.

[0321] In one embodiment of the present application, Ar4 to Ar6 of Chemical Formula 5 are 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 naphthyl group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted dibenzothiophenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted 9,9-dimethylfluorenyl group; a substituted or unsubstituted anthracenyl group; a substituted or unsubstituted pyrene group; a substituted or unsubstituted chrysene group; a substituted or unsubstituted fluoranthene group; a substituted or unsubstituted 9,9-diphenylfluorenyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted spirobifluorenyl group; or a substituted or unsubstituted triphenylene group.

[0322] In one embodiment of the present application, Ra of Chemical Formula 5 may be hydrogen; or deuterium.

[0323] In one embodiment of the present application, Rb of Chemical Formula 5 may be hydrogen; or deuterium.

[0324] In one embodiment of the present application, the heterocyclic compound represented by Chemical Formula 5 may be represented by any one of the following Chemical Formulas 5-1 to 5-11.

[0325] [Chemical formula 5-1]

[0326]

[0327] [Chemical formula 5-2]

[0328]

[0329] [Chemical formula 5-3]

[0330]

[0331] [Chemical formula 5-4]

[0332]

[0333] [Chemical formula 5-5]

[0334]

[0335] [Chemical formula 5-6]

[0336]

[0337] [Chemical formula 5-7]

[0338]

[0339] [Chemical formula 5-8]

[0340]

[0341] [Chemical formula 5-9]

[0342]

[0343] [Chemical formula 5-10]

[0344]

[0345] [Chemical formula 5-11]

[0346]

[0347] In Chemical Formula 5-1 to Chemical Formula 5-11,

[0348] Y1 to Y3, L3 to L6, Ar4 to Ar6, Ra, Rb, a, b, m3 to m5, n6 to n9, and p have the same definitions as in Chemical Formula 5.

[0349] In one embodiment of the present application, the heterocyclic compound represented by Chemical Formula 5 may not include deuterium as a substituent, or may have a deuterium content of, 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 100% or less, 90% or less, 80% or less, 70% or less, or 60% or less based on the total number of hydrogen atoms and deuterium atoms.

[0350] In one embodiment of the present application, the heterocyclic compound represented by Chemical Formula 5 may not contain deuterium, or may have a deuterium content of 1% to 100% based on the total number of hydrogen atoms and deuterium atoms.

[0351] In one embodiment of the present application, the heterocyclic compound represented by Chemical Formula 5 may not contain deuterium, or may have a deuterium content of 10% to 100% based on the total number of hydrogen atoms and deuterium atoms.

[0352] In one embodiment of the present application, the heterocyclic compound represented by Chemical Formula 5 may not contain deuterium, or may have a deuterium content of 20% to 90% based on the total number of hydrogen atoms and deuterium atoms.

[0353] In one embodiment of the present application, the heterocyclic compound represented by Chemical Formula 5 may not contain deuterium, or may have a deuterium content of 30% to 80% based on the total number of hydrogen atoms and deuterium atoms.

[0354] In one embodiment of the present application, the heterocyclic compound represented by Chemical Formula 5 may not contain deuterium, or may have a deuterium content of 40% to 70% based on the total number of hydrogen atoms and deuterium atoms.

[0355] In one embodiment of the present application, the heterocyclic compound represented by Chemical Formula 5 may have a deuterium content of 0% or more, 1% or more, 5% or more, 10% or more, 15% or more, 20% or more, 25% or more, 30% or more, 35% or more, 40% or more, 45% or more or 50% or more, and 100% or less, 95% or less, 90% or less, 85% or less, 80% or less, 75% or less, 70% or less, 65% or less, or 60% or less, based on the total number of hydrogen atoms and deuterium atoms.

[0356] One embodiment of the present application provides a heterocyclic compound, wherein Chemical Formula 5 is represented by any one of the following compounds. In addition, in one embodiment of the present application, the following compound is only an example, and the present application is not limited thereto, and may include other compounds included in Chemical Formula 5, including additional substituents.

[0357]

[0358]

[0359]

[0360]

[0361]

[0362]

[0363]

[0364]

[0365]

[0366]

[0367]

[0368]

[0369]

[0370] In addition, another embodiment of the present application provides a composition for an organic material layer, the composition including: a heterocyclic compound represented by Chemical Formula 1; and a heterocyclic compound represented by Chemical Formula 5.

[0371] Detailed descriptions about the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 5 are the same as those provided above.

[0372] In the composition, the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 5 may have a weight ratio of 1:10 to 10:1, 1:8 to 8:1, 1:5 to 5:1, or 1:2 to 2:1, however, the ratio is not limited thereto.

[0373] The composition can be used when forming an organic material of an organic light-emitting device, and more preferably can be used when forming a host of a light-emitting layer.

[0374] The composition has a form of a simple mixture of two or more compounds, and the materials in powder state can be mixed before forming the organic material layer of the organic light-emitting device, or the compounds in liquid state at an appropriate temperature can be mixed. The composition is solid below the melting point of each material, and can also remain in liquid state when the temperature is adjusted.

[0375] The composition may also include materials known in the art, such as solvents and additives.

[0376] The organic light-emitting device according to an embodiment of the present application can be manufactured using a common organic light-emitting device manufacturing method and materials, except that the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 5 are used to form one or more organic material layers.

[0377] When manufacturing an organic light-emitting device, the compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 5 can be formed into an organic material layer using a solution coating method and a vacuum deposition method. Here, the solution coating method means spin coating, dip coating, inkjet printing, screen printing, spray coating, roller coating, etc., but is not limited thereto.

[0378] The organic material layer of the organic light-emitting device of the present disclosure may be formed as a single-layer structure, but may also be formed as a multilayer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present disclosure may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron blocking layer, an electron injection layer, etc. as organic material layers. However, the structure of the organic light-emitting device is not limited thereto, and may include a smaller number of organic material layers.

[0379] In one embodiment of the present application, the organic light emitting device may be a blue organic light emitting device, and the heterocyclic compound according to Chemical Formula 1 and the heterocyclic compound according to Chemical Formula 5 may be used as a material of the blue organic light emitting device.

[0380] In one embodiment of the present application, the organic light emitting device may be a green organic light emitting device, and the compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 5 may be used as materials of the green organic light emitting device.

[0381] In one embodiment of the present application, the organic light emitting device may be a red organic light emitting device, and the compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 5 may be used as materials of the red organic light emitting device.

[0382] The organic light-emitting device of the present disclosure may further include one or two or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron injection layer, an electron transport layer, an electron blocking layer and a hole blocking layer.

[0383] One embodiment of the present application provides an organic light-emitting device, wherein the organic material layer includes at least one of a hole blocking layer, an electron injection layer, an electron blocking layer and an electron transport layer, and at least one of the hole blocking layer, the electron injection layer, the electron blocking layer and the electron transport layer includes a heterocyclic compound represented by Chemical Formula 1 and a heterocyclic compound represented by Chemical Formula 5.

[0384] One embodiment of the present application provides an organic light-emitting device, wherein the organic material layer includes a light-emitting layer, and the light-emitting layer includes a heterocyclic compound represented by Chemical Formula 1 and a heterocyclic compound represented by Chemical Formula 5.

[0385] One embodiment of the present application provides an organic light-emitting device, wherein the organic material layer includes a light-emitting layer, the light-emitting layer includes a host material, and the host material includes a heterocyclic compound represented by Chemical Formula 1 and a heterocyclic compound represented by Chemical Formula 5.

[0386] Figures 1 to 3 The stacking order of electrodes and organic material layers of an organic light-emitting device according to an embodiment of the present disclosure is shown. However, the scope of the present application is not limited by these drawings, and the structure of an organic light-emitting device known in the art can also be applied to the present application.

[0387] Figure 1 1 shows an organic light emitting device in which a positive electrode 200, an organic material layer 300 and a negative electrode 400 are sequentially stacked on a substrate 100. However, the structure is not limited to such a structure. Figure 2 As shown, an organic light-emitting device in which a negative electrode, an organic material layer and a positive electrode are sequentially stacked on a substrate can also be obtained.

[0388] Figure 3 The case where the organic material layer is multi-layered is shown. Figure 3 The organic light-emitting device 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 to such a stacked structure, and layers other than the light-emitting layer may not be included as needed, and other necessary functional layers may be further added.

[0389] An embodiment of the present disclosure provides a method for manufacturing an organic light-emitting device, the method comprising: preparing a substrate; forming a first electrode on the substrate; forming one or more organic material layers on the first electrode; and forming a second electrode on the organic material layer, wherein forming the organic material layer comprises forming one or more organic material layers using a composition for organic material layers according to an embodiment of the present disclosure.

[0390] In one embodiment of the present disclosure, the forming of the organic material layer may be forming the organic material layer using a thermal vacuum deposition method after premixing the heterocyclic compound represented by Chemical Formula 1.

[0391] Premixing means that before depositing the heterocyclic compound represented by Chemical Formula 1 on the organic material layer, the materials are placed in one supply source and mixed.

[0392] According to one embodiment of the present application, the premixed material may refer to a composition for an organic material layer.

[0393] The organic material layer including the heterocyclic compound represented by Chemical Formula 1 may further include other materials as needed.

[0394] In an organic light-emitting device according to an embodiment of the present disclosure, materials other than the heterocyclic compound represented by Chemical Formula 1 are exemplified below, however, these materials are only for illustrative purposes and do not limit the scope of the present application, and these materials may be replaced by materials known in the art.

[0395] As the positive electrode material, a material with a relatively large work function can be used, and a transparent conductive oxide, metal, conductive polymer, etc. can also be used. Specific examples of positive electrode materials include metals, such as vanadium, chromium, copper, zinc and gold or their alloys; metal oxides, such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); combinations of metals and oxides, such as ZnO:Al or SnO2:Sb; conductive polymers, such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole and polyaniline, etc., but are not limited thereto.

[0396] As the negative electrode material, a material with a relatively small work function can be used, and metals, metal oxides, conductive polymers, etc. can also be used. Specific examples of negative electrode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; multilayer structure materials such as LiF / Al or LiO2 / Al, etc., but are not limited thereto.

[0397] As the hole injection layer material, a known hole injection layer material can 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 such as tris(4-carbazolyl-9-ylphenyl)amine (TCTA), 4,4′,4″-tris[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA) or 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB) described in the document [Advanced Material, 6, p. 677 (1994)], a soluble conductive polymer such as polyaniline / dodecylbenzenesulfonic acid or poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate), polyaniline / camphorsulfonic acid or polyaniline / poly(4-styrenesulfonate),

[0398] As the hole transport layer material, pyrazoline derivatives, aromatic amine derivatives, stilbene derivatives, triphenyldiamine derivatives, etc. can be used, and low molecular weight or high molecular weight materials can also be used.

[0399] As electron transport layer materials, metal complexes of oxadiazole derivatives, anthraquinone dimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinone dimethane and its derivatives, fluorenone derivatives, diphenyldicyanoethylene and its derivatives, diphenoquinone derivatives, 8-hydroxyquinoline and its derivatives, etc. can be used, and polymer materials and low molecular weight materials can also be used.

[0400] As an example of the electron injection layer material, LiF is generally used in the art, however, the present application is not limited thereto.

[0401] As the light-emitting layer material, red, green or blue light-emitting materials can be used, and two or more light-emitting materials can be mixed and used as needed. Here, two or more light-emitting materials can be deposited as separate supply sources, or pre-mixed and deposited as one supply source when used. In addition, fluorescent materials can also be used as light-emitting layer materials, however, phosphorescent materials can also be used. As the light-emitting layer material, a material that emits light alone by combining holes and electrons injected from the positive electrode and the negative electrode respectively can be used, however, a material that participates in light emission together with a main material and a dopant material can also be used.

[0402] When the host of the light-emitting layer material is mixed and used, the host of the same series can be mixed and used, or the host of different series can be mixed and used. For example, any two or more types of materials in n-type host materials and p-type host materials can be selected and used as the host material of the light-emitting layer.

[0403] The organic light emitting device according to one embodiment of the present disclosure may be a top-emission type, a bottom-emission type, or a dual-emission type, depending on the materials used.

[0404] The heterocyclic compound according to one embodiment of the present disclosure may also be used in organic electronic devices including an organic solar cell, an organic photoconductor, an organic transistor, etc. under a similar principle to an organic light emitting device.

[0405] Hereinafter, preferred embodiments are provided to help understand the present disclosure, however, the following embodiments are provided only for easier understanding of the present disclosure, and the present disclosure is not limited thereto.

[0406] <Preparation Example>

[0407] <Preparation Example 1> Preparation of Compound 104

[0408]

[0409] 1) Preparation of compound 104-2

[0410] 1-Bromo-2-fluoro-3-iodobenzene (B) (48.3 g, 0.161 mol, 1.1 equivalents), K2CO3 (50.4 g, 0.365 mol, 2.5 equivalents), Pd(PPh3)4 (8.4 g, 0.008 mol, 0.05 equivalents), 1,4-dioxane (350 mL) and water (80 mL) were added to compound 104-1 (a) (34.5 g, 0.146 mol, 1 equivalent), and the mixture was stirred at 100°C for 6 hours. After the reaction was terminated by introducing water therein, the product was extracted with dichloromethane and water. Thereafter, MgSO4 was used to remove moisture. The product was separated using a silica gel column to obtain compound 104-2 (39 g) with a yield of 73%.

[0411] 2) Preparation of compound 104-3

[0412] Compound 104-2 (39 g, 0.107 mol, 1 equivalent) was dissolved in dichloromethane (390 mL), and then BBr3 (53.5 g, 0.213 mol, 2 equivalents) was slowly added dropwise at 0 ° C. The temperature was raised to room temperature, and then the mixture was stirred for 6 hours. After the reaction was terminated by introducing water therein, the product was extracted with dichloromethane and water. After that, MgSO4 was used to remove moisture. The product was separated using a silica gel column to obtain compound 104-3 (30 g) with a yield of 80%.

[0413] 3) Preparation of Compound 104-4

[0414] N, N-dimethylacetamide was introduced into compound 104-3 (30 g, 0.085 mol, 1 equivalent) and Cs2CO3 (15.5 g, 0.171 mol, 2 equivalents), and the mixture was stirred at 130°C for 10 hours. After the reaction was terminated by introducing water, the product was extracted with dichloromethane and water. Thereafter, MgSO4 was used to remove moisture. The product was separated using a silica gel column to obtain compound 104-4 (20 g) with a yield of 71%.

[0415] 4) Preparation of Compound 104-5

[0416] Phenylboronic acid (C) (8 g, 0.066 mol, 1.1 equiv.), K2CO3 (25 g, 0.180 mol, 3 equiv.), Pd(PPh3)4 (3.4 g, 0.004 mol, 0.05 equiv.), 1,4-dioxane (200 mL) and H2O (60 mL) were introduced into compound 104-4 (20 g, 0.060 mol, 1 equiv.), and the mixture was stirred at 100°C for 6 hours. After the reaction was terminated by introducing water therein, the product was extracted with dichloromethane and water. Thereafter, MgSO4 was used to remove moisture. The product was separated using a silica gel column to obtain compound 104-5 (15 g) with a yield of 76%.

[0417] 5) Preparation of Compound 104

[0418] N-phenyl-[1,1'-biphenyl]-4-amine (D) (6.3 g, 0.026 mol, 1.05 equiv.), NaOt-Bu (9 g, 0.036 mol, 1.5 equiv.), Pd2(dba)3 (1.1 g, 0.001 mol, 0.05 equiv.), Xphos (1.1 g, 0.002 mol, 0.1 equiv.), xylene (80 mL) were introduced into compound 104-5 (8 g, 0.024 mol, 1 equiv.), and the mixture was stirred at 140°C for 6 hours. After the reaction was terminated by introducing water therein, the product was extracted with dichloromethane and water. Thereafter, MgSO4 was used to remove moisture. The product was separated using a silica gel column to obtain compound 104 (8 g) with a yield of 54%.

[0419] <Preparation Example 2> Preparation of Compound 168

[0420]

[0421] 1) Preparation of Compound 168

[0422] N-([1,1'-biphenyl]-4-yl)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-[1,1'-biphenyl]-4-amine (D') (14.7 g, 0.029 mol, 1.05 equiv), K2CO3 (11 g, 0.080 mol, 3 equiv), Pd2(dba)3 (1.2 g, 0.001 mol, 0.05 equiv), Xphos (1.2 g, 0.002 mol, 0.1 equiv), 1,4-dioxane (90 mL) and H2O (90 mL) were introduced into compound 104-5 (9 g, 0.026 mol, 1 equiv), and the mixture was stirred at 100° C. for 8 hours. After the reaction was terminated by introducing water therein, the product was extracted with dichloromethane and water. After that, water was removed using MgSO4, and the product was separated using a silica gel column to obtain Compound 168 (12 g) with a yield of 64%.

[0423] <Preparation Example 3> Preparation of Compound NH5

[0424]

[0425] 1) Preparation of compound NH5-2

[0426] Phenylboronic acid (F) (6.7 g, 0.055 mol, 1.1 equiv.), KOAc (20.6 g, 0.149 mol, 3 equiv.), Pd(PPh3)4 (2.9 g, 0.002 mol, 0.05 equiv.), 1,4-dioxane (140 mL) and water (30 mL) were introduced into compound NH5-1(E) (16.5 g, 0.50 mol, 1 equiv.), and the mixture was stirred at 100°C for 6 hours. After the reaction was terminated by introducing water therein, the product was extracted with dichloromethane and water. Thereafter, MgSO4 was used to remove moisture. The product was separated using a silica gel column to obtain compound NH5-2 (12 g) with a yield of 73%.

[0427] 2) Preparation of compound NH5-3

[0428] 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) (13.7 g, 0.054 mol, 1.5 equiv), KOAc (10.6 g, 0.108 mol, 3 equiv), Pd2(dba)3 (1.6 g, 0.0018 mol, 0.05 equiv) and XPhos (1.7 g, 0.0036 mol, 0.1 equiv), 1,4-dioxane (100 mL) were introduced into compound NH5-2 (12 g, 0.036 mol, 1 equiv), and the mixture was stirred at 100° C. for 8 hours. After the reaction was terminated by introducing water therein, the product was extracted with dichloromethane and water. Thereafter, MgSO4 was used to remove moisture. The product was separated using a silica gel column to obtain compound NH5-3 (11.4 g) with a yield of 74%.

[0429] 3) Preparation of compound NH5

[0430] 2,4-di([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (G) (12.4 g, 0.030 mol, 1.1 equiv.), K2CO3 (11.2 g, 0.081 mol, 3 equiv.), Pd(PPh3)4 (1.6 g, 0.001 mol, 0.05 equiv.), 1,4-dioxane (100 mL) and water (20 mL) were introduced into compound NH5-3 (11.4 g, 0.027 mol, 1 equiv.), and the mixture was stirred at 100°C for 6 hours. After the reaction was terminated by introducing water therein, the product was extracted with dichloromethane and water. Thereafter, MgSO4 was used to remove moisture. The product was separated using a silica gel column to obtain compound NH5 (12 g) with a yield of 65%.

[0431] <Preparation Example 4> Preparation of compounds 14, 27, 35, 43, 80, 81, 120, 138, 147, 159, 172, 185, 189, 192, 197, 199, 201, 204, NH49, NH88, NH112, NH153, NH179 and NH206

[0432] Compounds 14, 27, 35, 43, 80, 81, 120, 138, 147, 159, 172, 185, 189, 192, 197, 199, 201, 204, NH49, NH88, NH112, NH153, NH179 and NH206 were synthesized as shown in Table 1 below in the same manner as in Preparation Examples 1 to 3, except that intermediates A, B, C, D, E, F and G in Table 1 below were used instead of (A), (B), (C), (D), (D'), (E), (F) and (G).

[0433]

Table 1

[0434]

[0435]

[0436]

[0437]

[0438] <Preparation Example 5> Preparation of Compound 203

[0439]

[0440] 1) Preparation of Compound 203

[0441] After introducing compound 43 (7 g, 0.011 mol, 1 eq.), TfOH (2.7 g, 0.018 mol, 1.5 eq.) and D6-benzene (70 mL), the mixture was stirred at 80° C. for 6 hours. After the reaction was terminated by introducing water therein, the product was extracted with dichloromethane and water. Thereafter, MgSO4 was used to remove moisture. The product was separated using a silica gel column to obtain compound 203 (6 g) with a yield of 82%.

[0442] The remaining compounds other than the compounds described in Preparation Examples 1 to 5 and Table 1 were also prepared in the same manner as the above Preparation Examples, and the synthesis and identification results are shown in Tables 2 and 3 below. Table 2 shows 1 Table 3 shows the measured values ​​by H NMR (CDCl3, 200 MHz) and the measured values ​​by FD mass spectrometry (FD-MS: field desorption mass spectrometry).

[0443]

Table 2

[0444]

[0445]

Table 3

[0446] Compound FD-MS Compound FD-MS 14 m / z=587.22 192 m / z=717.23 27 m / z=627.22 197 m / z=739.29 35 m / z=777.30 199 m / z=765.94 43 m / z=613.24 201 m / z=618.27 80 m / z=719.23 203 m / z=644.44 81 m / z=689.27 204 m / z=631.35 104 m / z=613.24 NH5 m / z=677.25 120 m / z=699.26 NH49 m / z=615.19 138 m / z=689.27 NH88 m / z=601.22 147 m / z=677.24 NH112 m / z=665.21 159 m / z=713.27 NH153 m / z=651.23 172 m / z=729.30 NH179 m / z=615.19 185 m / z=663.26 NH206 m / z=625.22 189 m / z=719.23

[0447] <Experimental Example 1>

[0448] 1) Manufacturing of organic light-emitting devices

[0449] The transparent electrode indium tin oxide (ITO) film obtained from OLED glass (manufactured by Samsung Corning Advanced Glass) was ultrasonically cleaned with trichloroethylene, acetone, ethanol and distilled water for 5 minutes each, and then stored in isopropyl alcohol before use. Then, the ITO substrate was mounted in a substrate holder of a vacuum deposition device, and the following 4,4',4"-tri(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) was introduced into the unit in the vacuum deposition device.

[0450]

[0451] The chamber was then evacuated until the vacuum level reached 10 -6 Then, 2-TNATA was evaporated by applying current to the cell to deposit a thickness of The following N, N'-bis (α-naphthyl) -N, N'-diphenyl-4, 4'-diamine (NPB) was introduced into another unit in the vacuum deposition apparatus, and NPB was evaporated by applying a current to the unit, thereby depositing a thickness of hole transport layer.

[0452]

[0453] After forming the hole injection layer and the hole transport layer as described above, a blue light emitting material having the following structure is deposited thereon as a light emitting layer. Specifically, BH1 as a blue light emitting main material is vacuum deposited onto a unit in a vacuum deposition device. and vacuum deposited D1 as a blue light emitting dopant material to a thickness of 5% relative to the host material.

[0454]

[0455] Subsequently, a compound having the following structural formula E1 is deposited onto The thickness of the layer serves as an electron transport layer.

[0456]

[0457] Lithium fluoride (LiF) is deposited on The thickness of the electron injection layer is At the same time, for each material used to make OLED, the Al negative electrode was 10 -8 Support up to 10 -6 All organic compounds required for manufacturing OLEDs were purified by vacuum sublimation under vacuum. An organic electroluminescent device was manufactured in the same manner as in Experimental Example 1, except that the compounds listed in Table 4 below were used instead of NPB used in forming the hole transport layer in Experimental Example 1.

[0458] The measurement results of the driving voltage, luminous efficiency, color coordinates (CIE), and lifetime of the blue organic light emitting device manufactured according to the present disclosure are shown in Table 4 below.

[0459]

Table 4

[0460]

[0461]

[0462] The comparative compounds used in Table 4 are as follows.

[0463]

[0464] It can be seen from the results in Table 4 that the organic light-emitting device using the hole transport layer material of the blue organic light-emitting device disclosed in the present invention has a lower driving voltage than that of Comparative Examples 1 to 15, and the luminous efficiency and life span are significantly improved.

[0465] The HOMO orbital region in the organic light-emitting device has hole transport properties in the molecule, and it can be seen that compared with the compound of the example, the HOMO orbital region in the naphtho[2,1-b]benzofuran functional group has a hole transport property. The comparative example compounds H2 and H4 including two amine groups and H7 including a carbazole functional group have deep HOMO energy levels. The preferred HOMO energy level for the hole transport layer is about -4.7 to -5.0 eV, and the compound including two amine groups and a carbazole group has an energy level that is not suitable for the hole transport layer. When the naphtho[2,1-b]benzofuran derivative according to the example of the present disclosure is used as a hole transport material, a faster hole mobility can be obtained compared with H1 using a benzonaphtho[1,2-d]thiophene functional group and H5 using a benzo[c]fluorene functional group, which is more advantageous for low voltage driving.

[0466] In addition, in Comparative Examples 2 to 15, the positions and numbers of the aromatic groups or amine groups forming the bonds are different. All organic materials in organic light-emitting devices need to have the property of being stably present as an amorphous film. By having a substituent at an appropriate position, the pi-pi stacking of the aromatic ring can be suppressed, thereby improving the device stability and preventing the degradation of the device characteristics. Therefore, it can be seen that the compounds of the present disclosure using such derivatives have excellent properties in all aspects of driving, efficiency and life.

[0467] <Experimental Example 2>

[0468] 1) Manufacturing of organic light-emitting devices

[0469] The transparent electrode indium tin oxide (ITO) film obtained from OLED glass (manufactured by Samsung Corning Advanced Glass) was ultrasonically cleaned with trichloroethylene, acetone, ethanol and distilled water for 5 minutes each, and then stored in isopropyl alcohol before use. Then, the ITO substrate was mounted in a substrate holder of a vacuum deposition device, and the following 4,4',4"-tri(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) was introduced into the unit in the vacuum deposition device.

[0470]

[0471] The chamber was then evacuated until the vacuum level reached 10 -6 Then, 2-TNATA was evaporated by applying current to the cell to deposit a thickness of The following N, N'-bis (α-naphthyl) -N, N'-diphenyl-4, 4'-diamine (NPB) was introduced into another unit in the vacuum deposition apparatus, and NPB was evaporated by applying a current to the unit, thereby depositing a thickness of hole transport layer.

[0472]

[0473] After forming the hole injection layer and the hole transport layer as described above, a blue light emitting material having the following structure is deposited thereon as a light emitting layer. Specifically, BH1 as a blue light emitting main material is vacuum deposited onto a unit in a vacuum deposition device. and vacuum deposited D1 as a blue light emitting dopant material to a thickness of 5% relative to the host material.

[0474]

[0475] Subsequently, a compound having the following structural formula E1 is deposited onto The thickness of the layer serves as an electron transport layer.

[0476]

[0477] Lithium fluoride (LiF) is deposited on The thickness of the electron injection layer is At the same time, for each material used to make OLED, the Al negative electrode was 10 -8 Support up to 10 -6 Vacuum sublimation under vacuum purifies all the organic compounds needed to manufacture OLEDs.

[0478] An organic electroluminescent device was manufactured in the same manner as in Example 2, except that the hole transport layer NPB was formed as Then, an electron blocking layer was formed on the hole transport layer by using the compounds listed in Table 5 below. The measurement results of the driving voltage, luminous efficiency, color coordinates (CIE) and lifespan of the blue organic light-emitting device manufactured according to the present disclosure are shown in Table 5 below.

[0479]

Table 5

[0480]

[0481] The comparative compounds used in Table 5 are as follows.

[0482]

[0483] It can be seen from the results in Table 5 that the organic light-emitting device using the electron blocking layer material of the blue organic light-emitting device disclosed in the present invention has a lower driving voltage than that of Comparative Examples 16 to 30, and the luminous efficiency and life span are significantly improved.

[0484] Compared with the comparative example, the organic light-emitting device using the electron blocking layer material of the blue organic light-emitting device disclosed in the present invention has a lower driving voltage, and the luminous efficiency and life are improved. When electrons pass through the hole transport layer and migrate to the positive electrode without combining in the light-emitting layer, the efficiency and life of the OLED are reduced. When a compound with a high LUMO energy level is used in the electron blocking layer to prevent this phenomenon, the electrons trying to pass through the light-emitting layer and migrate to the positive electrode are blocked by the energy barrier of the electron blocking layer. As a result, the probability of holes and electrons forming excitons increases, and the possibility of them being emitted as light in the light-emitting layer increases. Therefore, it can be seen that the compounds disclosed in the present invention bring excellence in all aspects of driving, efficiency and life.

[0485] In addition, in Comparative Examples 16 to 30, the positions and numbers of the aromatic groups or amine groups forming the bonds are different. All organic materials in organic light-emitting devices need to have the property of being stable as an amorphous film. By having a substituent at an appropriate position, the pi-pi stacking of the aromatic ring can be suppressed, thereby improving the device stability and preventing the degradation of the device characteristics. Therefore, it can be seen that the compounds of the present disclosure using such derivatives have excellent properties in all aspects of driving, efficiency and life.

[0486] <Experimental Example 3>

[0487] 1) Manufacturing of organic light-emitting devices

[0488] Distilled water was applied to the The glass substrate of indium tin oxide (ITO) is ultrasonically cleaned. After cleaning with distilled water, the substrate is ultrasonically cleaned with solvents such as acetone, methanol, and isopropanol, then dried, and then treated with ultraviolet ozone (UVO) for 5 minutes using UV in an ultraviolet (UV) cleaner. After that, the substrate is transferred to a plasma cleaner (PT), and then plasma treated under vacuum for ITO work function and residual film removal, and transferred to a thermal deposition device for organic deposition.

[0489] On the transparent ITO electrode (positive electrode), a hole injection layer 2-TNATA (4,4′,4″-tri[2-naphthyl(phenyl)amino]triphenylamine), a hole transport layer NPB (N,N′-di(1-naphthyl)-N,N′-diphenyl-(1,1′-biphenyl)-4,4′-diamine) and an electron blocking layer TAPC (cyclohexylenebis[N,N-bis(4-methylphenyl)aniline) are formed as common layers.

[0490] The light emitting layer was thermally vacuum deposited thereon as follows. The light emitting layer was deposited on the host by depositing two types of compounds described in Table 6 below as a red host in one supply source and using [(piq)2(Ir)(acac)] as a red phosphorescent dopant to dope the host with 3 wt % Ir compound. Afterwards, Bphen was deposited onto As a hole blocking layer, TPBI is deposited on it. As electron transport layer.

[0491] Finally, a layer with a thickness of LiF is used to form an electron injection layer, and then a layer with a thickness of An aluminum (Al) negative electrode is formed to form a negative electrode, resulting in the manufacture of an organic electroluminescent device.

[0492] At the same time, for each material used to make OLEDs,-8 Support up to 10 -6 All organic compounds required for manufacturing OLEDs were purified by vacuum sublimation under a support. For each organic electroluminescent device manufactured as described above, electroluminescence (EL) characteristics were measured using M7000 manufactured by McScience, and based on the measurement results, the lifetime measurement system (M6000) manufactured by McScience was used at a standard brightness of 6000 cd / m 2 Time measurement T 90 The measurement results of the driving voltage, luminous efficiency, color coordinates (CIE) and lifespan of the organic light-emitting device manufactured according to the present disclosure are shown in Table 6.

[0493]

Table 6

[0494]

[0495] The comparative compounds used in Table 6 are as follows.

[0496]

[0497] As can be seen from the results of Table 6, when the heterocyclic compound of the present disclosure is used as a P-type host and mixed with an N-type host for deposition, the organic light-emitting device has improved driving efficiency and life. When a donor (p-host) with good hole transport ability and an acceptor (n-host) with 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 due to the excitation complex phenomenon of the n+p compound, so that the charge balance in the device can be adjusted. It can be seen that combining an N-type host compound with appropriate electron transfer and a P-type host compound with appropriate hole transfer in an appropriate ratio can help improve driving efficiency and life.

Claims

1. A heterocyclic compound, characterized in that The heterocyclic compound is represented by the following chemical formula 1: [Chemical formula 1] Wherein, in Chemical Formula 1, A1 to A4 and B1 to B6 are the same as or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1-C60 alkyl; substituted or unsubstituted C2-C60 alkenyl; substituted or unsubstituted C2-C60 alkynyl; substituted or unsubstituted C1-C60 alkoxy; substituted or unsubstituted C3-C60 cycloalkyl; substituted or unsubstituted C2-C60 heterocycloalkyl; substituted or unsubstituted C6-C60 aryl; substituted or unsubstituted C2-C60 heteroaryl; and a group represented by the following Chemical Formula 2, and at least one of A1 to A4 and B1 to B4 is represented by the following Chemical Formula 2; and When any one of A1 to A4 is a group represented by the following Chemical Formula 2, any one of B1 to B4 is represented by a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group, or When any one of B1 to B4 is a group represented by the following Chemical Formula 2, any one of A1 to A4 is represented by a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group, [Chemical formula 2] In chemical formula 2, Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group; L1 to L3 are the same as or different from each other and are each independently a single bond; a substituted or unsubstituted C6-C60 arylene group; or a substituted or unsubstituted C2-C60 heteroarylene group; m1 and m2 are integers from 0 to 5; and n1 to n3 are the same or different and are each independently an integer of 0 to 4.

2. The heterocyclic compound according to claim 1, characterized in that Chemical formula 1 is represented by the following chemical formulas 1-1 to 1-8: [Chemical formula 1-1] [Chemical formula 1-2] [Chemical formula 1-3] [Chemical formula 1-4] [Chemical formula 1-5] [Chemical formula 1-6] [Chemical formula 1-7] [Chemical formula 1-8] In Chemical Formulas 1-1 to 1-8, A1 to A4, B1 to B6, Ar1, Ar2, L1 to L3, m1, m2, n1 to n3 have the same definitions as in Chemical Formula 1; At least one of B1 to B4 in Chemical Formulae 1-1 to 1-4 is represented by a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group; and At least one of A1 to A4 in Chemical Formulae 1-5 to 1-8 is represented by a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group.

3. The heterocyclic compound according to claim 1, characterized in that Ar1 and Ar2 are represented by any one of the following chemical formulas 3 and 4: [Chemical formula 3] [Chemical formula 4] In Chemical Formula 3 and Chemical Formula 4, X1 is O, S or CRaRb; Ar3 is a substituted or unsubstituted C6-C60 aryl group; R1, R2, Ra and Rb are the same as or different from each other and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1-C60 alkyl; substituted or unsubstituted C2-C60 alkenyl; substituted or unsubstituted C2-C60 alkynyl; substituted or unsubstituted C1-C60 alkoxy; substituted or unsubstituted C3-C60 cycloalkyl; substituted or unsubstituted C2-C60 heterocycloalkyl; substituted or unsubstituted C6-C60 aryl; and substituted or unsubstituted C2-C60 heteroaryl, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6-C60 aromatic hydrocarbon ring; or a substituted or unsubstituted C2-C60 heterocycle; n4 is an integer from 0 to 4; and n5 is an integer from 0 to 3.

4. The heterocyclic compound according to claim 1, characterized in that The heterocyclic compound represented by Chemical Formula 1 does not include deuterium as a substituent, or has a deuterium content of 1% to 100% based on the total number of hydrogen atoms and deuterium atoms.

5. The heterocyclic compound according to claim 1, characterized in that The heterocyclic compound represented by Chemical Formula 1 is represented by any one of the following compounds:

6. An organic light-emitting device, comprising: a first electrode; a second electrode, arranged opposite to the first electrode; as well as One or more organic material layers are disposed between the first electrode and the second electrode, One or more layers of the organic material layer include the heterocyclic compound according to any one of claims 1 to 5.

7. The organic light emitting device according to claim 6, characterized in that: The organic material layer includes a light emitting layer, and the light emitting layer includes a heterocyclic compound represented by Chemical Formula 1.

8. The organic light emitting device according to claim 6, characterized in that: The organic material layer includes a light emitting layer, the light emitting layer includes a host material, and the host material includes a heterocyclic compound represented by Chemical Formula 1.

9. The organic light emitting device according to claim 6, characterized in that: The organic material layer further includes a heterocyclic compound represented by the following Chemical Formula 5: [Chemical formula 5] In Chemical Formula 5, Y1 to Y3 are the same as or different from each other and are each independently CH or N, and at least one of Y1 to Y3 is N; L3 to L6 are the same as or different from each other and are each independently a single bond; a substituted or unsubstituted C6-C60 arylene group; or a substituted or unsubstituted C2-C60 heteroarylene group; Ar4 to Ar6 are the same as or different from each other, and are each independently a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group; m3 to m5 are the same as or different from each other, and are each independently an integer from 0 to 5; n6 to n9 are the same as or different from each other and are each independently an integer from 0 to 4; p is an integer of 0 or 1; Ra and Rb are the same as or different from each other and are each hydrogen or deuterium; a is an integer from 0 to 4; b is an integer from 0 to 6; and When p is 0, b is an integer from 0 to 4.

10. The organic light emitting device according to claim 9, characterized in that: The heterocyclic compound represented by Chemical Formula 5 does not include deuterium as a substituent, or has a deuterium content of 1% to 100% based on the total number of hydrogen atoms and deuterium atoms.

11. The organic light emitting device according to claim 9, characterized in that: The heterocyclic compound represented by Chemical Formula 5 is represented by any one of the following compounds:

12. The organic light emitting device according to claim 6, characterized in that: It also includes one, or two or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron injection layer, an electron transport layer, an electron blocking layer and a hole blocking layer.

13. A composition for an organic material layer, comprising: The heterocyclic compound according to any one of claims 1 to 5; as well as A heterocyclic compound represented by the following Chemical Formula 5: [Chemical formula 5] Among them, in chemical formula 5, Y1 to Y3 are the same as or different from each other and are each independently CH or N, and at least one of Y1 to Y3 is N; L3 to L6 are the same as or different from each other and are each independently a single bond; a substituted or unsubstituted C6-C60 arylene group; or a substituted or unsubstituted C2-C60 heteroarylene group; Ar4 to Ar6 are the same as or different from each other, and are each independently a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group; m3 to m5 are the same as or different from each other, and are each independently an integer from 0 to 5; n6 to n9 are the same as or different from each other and are each independently an integer from 0 to 4; p is an integer of 0 or 1; Ra and Rb are the same as or different from each other and are each hydrogen or deuterium; a is an integer from 0 to 4; b is an integer from 0 to 6; and When p is 0, b is an integer from 0 to 4.

14. The composition according to claim 13, characterized in that The weight ratio of the heterocyclic compound represented by Chemical Formula 1 to the heterocyclic compound represented by Chemical Formula 5 in the composition is 1:10 to 10:1.

Images