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

Abstract

The present invention provides a hetero-cyclic compound, an organic light emitting device including the same, and a composition for an organic material layer.SOLUTION: The present invention relates to a hetero-cyclic compound represented by Chemical Formula 1, and an organic light emitting device and a composition for an organic material layer comprising the same. The definition of each substituent in Formula 1 is the same as described in the description of the invention.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] This application claims the benefit of priority based on Korean Patent Application No. 10-2024-0094249, filed July 17, 2024, and Korean Patent Application No. 10-2025-0066869, filed May 22, 2025, and includes all contents disclosed in the documents of the relevant Korean patent applications as part of the specification. The present invention relates to a heterocyclic compound, an organic light-emitting device containing the same, and a composition for an organic layer. [Background technology]

[0002] As a type of self-luminous display device, the organic light-emitting element has advantages such as a wide viewing angle, excellent contrast, and fast response speed. An organic light-emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to an organic light-emitting device with this structure, electrons and holes injected from the two electrodes combine in the organic thin film to form pairs, and then annihilate, emitting light. The organic thin film may be configured as a single layer or multiple layers as needed.

[0003] The organic thin film material may have a light-emitting function as needed. For example, the organic thin film material may be a compound that can form an emitting layer by itself, or a compound that can function as a host or dopant in a host-dopant emitting layer. In addition, the organic thin film material may be a compound that can perform functions such as hole injection, hole transport, electron blocking, hole blocking, electron transport, or electron injection. In order to improve the performance, lifetime, or efficiency of organic light-emitting devices, there is a continuous demand for the development of organic thin film materials. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] U.S. Patent No. 4,356,429 Summary of the Invention [Problem to be solved by the invention]

[0005] The present invention provides a heterocyclic compound, an organic light-emitting device containing the same, and a composition for an organic layer. [Means for solving the problem]

[0006] In one embodiment of the present application, there is provided a heterocyclic compound represented by the following Chemical Formula 1: [ka]

[0007] In the above Chemical Formula 1, Y1 to Y3 are the same or different and each independently represents CH; or N; At least one of Y1 to Y3 is N, Ar1 and Ar2 are the same or different and each independently represent a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; L1 and L2 are the same or different and each independently represent a single bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group; R1 are the same or different and each independently represent hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or unsubstituted C2 to C60 heterocycloalkyl group; substituted or unsubstituted C6 to C60 aryl group; or substituted or unsubstituted C2 to C60 heteroaryl group; R2 to R9 are the same or different and each independently represent hydrogen; deuterium; a C1 to C60 alkyl group substituted or unsubstituted with deuterium; a C3 to C60 cycloalkyl group substituted or unsubstituted with deuterium; a C2 to C60 heterocycloalkyl group substituted or unsubstituted with deuterium; a C6 to C60 aryl group substituted or unsubstituted with deuterium; or a C2 to C60 heteroaryl group substituted or unsubstituted with deuterium; At least one of R2 to R9 is a deuterium or a C6 to C60 aryl group substituted with deuterium, n1 is an integer from 0 to 8, n2 and n3 are the same or different and each independently represents an integer of 0 to 4, When n1, n2 and n3 are 2 or more, R1, L1 and L2 are the same or different.

[0008] In addition, one embodiment of the present application provides an organic light-emitting device in which the organic material layer containing the heterocyclic compound represented by Chemical Formula 1 further contains a heterocyclic compound represented by Chemical Formula 2 or Chemical Formula 3 below.

[0009] [ka]

[0010] [ka]

[0011] In the above Chemical Formula 2 and Chemical Formula 3, L3 to L7 are the same or different and each independently represent a single bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group; Ar4 to Ar7 are the same or different and each independently represent a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, R15 to R19 are the same or different and each independently represent hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C2 to C60 alkenyl group; substituted or unsubstituted C2 to C60 alkynyl group; substituted or unsubstituted C1 to C60 alkoxy group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or unsubstituted C2 to C60 heterocycloalkyl group; substituted or unsubstituted C6 to C60 aryl group; or substituted or unsubstituted C2 to C60 heteroaryl. or -SiR101R102R103; or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same or different and each independently represent a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, m1 to m5 are the same or different and each independently represents an integer of 0 to 3, e and f are the same or different and each independently represents an integer of 0 to 7; g and h are the same or different and each independently represents an integer of 0 to 4, i is an integer from 0 to 2, When m1 to m5, e, f, g, h, and i are 2 or more, L3 to L7 and R15 to R19 are the same as or different from each other.

[0012] Another embodiment of the present application provides a composition for an organic layer, comprising the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2 or Chemical Formula 3. [Effects of the Invention]

[0013] The heterocyclic compound according to an embodiment can be used as an organic layer material of an organic light-emitting device. The compound can serve as a hole injection layer material, a hole transport layer material, an emission layer material, an electron transport layer material, an electron injection layer material, etc. In particular, the compound can be used as an emission layer material of an organic light-emitting device, or the compound can be used alone as an emission material, or as a host material or dopant material of the emission layer. When the heterocyclic compound represented by Chemical Formula 1 is used in the organic material layer, the driving voltage of the organic light emitting device is reduced, the luminous efficiency is increased, and the life characteristics are improved. [Brief explanation of the drawings]

[0014] [Figure 1] 1 is a diagram illustrating a stacked structure of an organic light emitting device according to an embodiment of the present invention; [Figure 2] 1 is a diagram illustrating a stacked structure of an organic light emitting device according to an embodiment of the present invention; [Figure 3] 1 is a diagram illustrating a stacked structure of an organic light emitting device according to an embodiment of the present invention; DETAILED DESCRIPTION OF THE INVENTION

[0015] The present invention will now be described in more detail. In this specification, when a part "comprises" a certain component, this does not mean that it excludes other components, but that it may further include other components, unless otherwise specified.

[0016] As used herein, the term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position of substitution is not limited as long as it is a position at which a hydrogen atom is substituted, i.e., a position at which a substituent can be substituted, and when two or more substituents are substituted, the two or more substituents may be the same or different from each other.

[0017] In this specification, the term "substituted or unsubstituted" means substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium; halogen; cyano group; C1 to C60 straight-chain or branched-chain alkyl group; C2 to C60 straight-chain or branched-chain alkenyl group; C2 to C60 straight-chain or branched-chain alkynyl group; C3 to C60 monocyclic or polycyclic cycloalkyl group; C2 to C60 monocyclic or polycyclic heterocycloalkyl group; C6 to C60 monocyclic or polycyclic aryl group; C2 to C60 monocyclic or polycyclic heteroaryl group; -SiRR'R"; -P(=O)RR'; C1 to C20 alkylamine group; C6 to C60 monocyclic or polycyclic arylamine group; and C2 to C60 monocyclic or polycyclic heteroarylamine group, or substituted or unsubstituted with a substituent in which two or more substituents selected from the above-mentioned substituents are linked together.

[0018] As used herein, "substituted or unsubstituted with deuterium" means that one or more of the substituted positions are substituted with deuterium; not all of the substituted positions should be substituted with deuterium; it is sufficient that only one or more of the substituted positions are substituted with deuterium; positions that are not substituted with deuterium are considered to be unsubstituted.

[0019] The R, R', and R" may be the same or different, and each may independently be a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group. In this specification, the halogen may be fluorine, chlorine, bromine or iodine.

[0020] In this specification, alkyl groups include straight or branched chain alkyl groups 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 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-ethyl ... Examples of alkyl groups include, but are not limited to, butyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylheptyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 4-methylhexyl, and 5-methylhexyl.

[0021] In this specification, the term "alkenyl group" refers to a straight or branched chain alkenyl group having 2 to 60 carbon atoms, which may be further substituted with other substituents. The alkenyl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 2 to 20 carbon atoms. Specific examples include, but are not limited to, 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-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl, and styrenyl.

[0022] In this specification, an alkynyl group includes a straight or branched chain 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.

[0023] In this specification, the alkoxy group may be linear, branched, or cyclic. The number of carbon atoms in the alkoxy group is not particularly limited, but preferably 1 to 20. Specific examples include, but are not limited to, a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, an isobutoxy group, a tert-butoxy group, a sec-butoxy group, an n-pentyloxy group, a neopentyloxy group, an isopentyloxy group, an n-hexyloxy group, a 3,3-dimethylbutyloxy group, a 2-ethylbutyloxy group, an n-octyloxy group, an n-nonyloxy group, an n-decyloxy group, a benzyloxy group, and a p-methylbenzyloxy group.

[0024] In this specification, the term "cycloalkyl group" refers to a monocyclic or polycyclic group having 3 to 60 carbon atoms, which may be further substituted with other substituents. Here, "polycyclic" refers to a group in which a cycloalkyl group is directly linked to or condensed with another cyclic group. Here, the other cyclic group may be a cycloalkyl group, but it may also be other types of cyclic groups, such as a heterocycloalkyl group, an aryl group, or a heteroaryl group. The number of carbon atoms in the cycloalkyl group may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20. Specific examples of the cycloalkyl group include, but are not limited to, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 3-methylcyclopentyl group, a 2,3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 2,3-dimethylcyclohexyl group, a 3,4,5-trimethylcyclohexyl group, a 4-tert-butylcyclohexyl group, a cycloheptyl group, and a cyclooctyl group.

[0025] In this specification, the heterocycloalkyl group contains O, S, Se, N, or Si as a heteroatom, and includes a monocyclic or polycyclic group having 2 to 60 carbon atoms, which may be further substituted with other substituents. Here, the term "polycyclic group" refers to a group in which the heterocycloalkyl group is directly linked to or condensed with another cyclic group. Here, the other cyclic group may be a heterocycloalkyl group, but may also be other types of cyclic groups, such as a cycloalkyl group, an aryl group, or a heteroaryl group. The number of carbon atoms in the heterocycloalkyl group may be 2 to 60, specifically 2 to 40, more specifically 3 to 20.

[0026] In this specification, the aryl group includes a monocyclic or polycyclic ring having 6 to 60 carbon atoms, and may be further substituted with other substituents. Here, the polycyclic ring means a group in which an aryl group is directly linked to or condensed with another cyclic group. Here, the other cyclic group may be an aryl group, but may also be other types of cyclic groups, such as a cycloalkyl group, a heterocycloalkyl group, or a heteroaryl group. The aryl group may contain a spiro group. The number of carbon atoms in the aryl group may be 6 to 60, specifically 6 to 40, more specifically 6 to 25. Specific examples of the aryl group include, but are not limited to, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a chrysenyl group, a phenanthrenyl group, a perylenyl group, a fluoranthenyl group, a triphenylenyl group, a phenalenyl group, a pyrenyl group, a tetracenyl group, a pentacenyl group, a fluorenyl group, an indenyl group, an acenaphthylenyl group, a benzofluorenyl group, a spirobifluorenyl group, a 2,3-dihydro-1H-indenyl group, and fused ring groups thereof.

[0027] In this specification, the phosphine oxide group is represented by -P(=O)R101R102, where R101 and R102 may be the same or different and each independently represent at least one substituent selected from the group consisting of hydrogen, deuterium, halogen, alkyl, alkenyl, alkoxy, cycloalkyl, aryl, and heterocyclic groups. Specifically, the phosphine oxide group may be substituted with an aryl group, and the aryl group may be any of the above-mentioned examples. Examples of the phosphine oxide group include, but are not limited to, diphenylphosphine oxide and dinaphthylphosphine oxide.

[0028] In this specification, the silyl group refers to a substituent containing Si and directly linked to the Si atom as a radical, and is represented by -SiR101R102R103, where R101 to R103 may be the same or different and each independently represent at least one of hydrogen, deuterium, halogen, alkyl, alkenyl, alkoxy, cycloalkyl, aryl, and heterocyclic groups. Specific examples of the silyl group include, but are not limited to, trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl.

[0029] Herein, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

[0030] When the fluorenyl group is substituted, it may have the following structural formula, but is not limited to this: [ka]

[0031] In this specification, a spiro group is a group containing a spiro structure and may have 15 to 60 carbon atoms. For example, the spiro group may have a structure in which a 2,3-dihydro-1H-indene group or a cyclohexane group is spiro-bonded to a fluorenyl group. Specifically, the spiro group may have any one of the groups represented by the following structural formulas: [ka]

[0032] In this specification, the heteroaryl group contains S, O, Se, N, or Si as a heteroatom, includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted with other substituents. Here, the polycyclic ring refers to a group in which the heteroaryl group is directly linked to or fused with another cyclic group. Here, the other cyclic group may be a heteroaryl group, but may also be other types of cyclic groups, such as a cycloalkyl group, a heterocycloalkyl group, or an aryl group. The number of carbon atoms in the heteroaryl group may be 2 to 60, specifically 2 to 40, more specifically 3 to 25.Specific examples of the heteroaryl group include a pyridyl group, a pyrrolyl group, a pyrimidyl group, a pyridazinyl group, a furanyl group, a thiophene group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, a furazanyl group, an oxadiazolyl group, a thiadiazolyl group, a dithiazolyl group, a tetrazolyl group, a pyranyl group, a thiopyranyl group, a diazinyl group, an oxazinyl group, a thiazinyl group, a dioxinyl group, a triazolyl group, a an azinyl group, a tetrazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, an isoquinazolinyl group, a quinozolinyl group, a naphthyridyl group, an acridinyl group, a phenanthridinyl group, an imidazopyridinyl group, a diazanaphthalenyl group, a triazaindene group, a 2-indolyl group, an indolizinyl group, a benzothiazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiophenyl group, a benzofuranyl group, a dibenzothiophenyl group, a dibenzofuranyl group, Carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, phenazinyl group, dibenzosilole group, spirobi(dibenzosilole) group, dihydrophenazinyl group, phenoxazinyl group, phenanthridyl group, thienyl group, indolo[2,3-a]carbazolyl group, indolo[2,3-b]carbazolyl group, indolinyl group, 10,11-dihydro-dibenzo[b,f]azepinyl group, 9,10-dihydroacridinyl group, phenanthrazinyl group, f Examples of such an alkyl group include, but are not limited to, a benzothiazinyl group, a phthalazinyl group, a naphthyridinyl group, a phenanthrolinyl group, a benzo[c][1,2,5]thiadiazolyl group, a 5,10-dihydrodibenzo[b,e][1,4]azasilinyl group, a pyrazolo[1,5-c]quinazolinyl group, a pyrido[1,2-b]indazolyl group, a pyrido[1,2-a]imidazo[1,2-e]indolinyl group, and a 5,11-dihydroindeno[1,2-b]carbazolyl group.

[0033] In this 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 preferably is 1 to 30. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, a dibiphenylamine group, an anthracenylamine group, a 9-methylanthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a triphenylamine group, a biphenylnaphthylamine group, a phenylbiphenylamine group, a biphenylfluorenylamine group, a phenyltriphenylenylamine group, and a biphenyltriphenylenylamine group, but are not limited to these.

[0034] In this specification, an arylene group refers to an aryl group having two bonding positions, i.e., a divalent group. The same explanation as for the aryl group applies to these groups, except that they are both divalent groups. Furthermore, a heteroarylene group refers to a heteroaryl group having two bonding positions, i.e., a divalent group. The same explanation as for the heteroaryl group applies to these groups, except that they are both divalent groups.

[0035] As used herein, the term "adjacent" refers to a substituent substituted on an atom directly linked to the atom on which the substituent is substituted, a substituent sterically closest to the substituent, or another substituent substituted on the atom on which the substituent is substituted. For example, two substituents substituted at ortho positions on a benzene ring and two substituents substituted on the same carbon atom on an aliphatic ring can be interpreted as groups "adjacent" to each other.

[0036] In this specification, when "no substituents are shown in the chemical formula or compound structure," it means that hydrogen atoms are bonded to carbon atoms. However, since deuterium (2H) is an isotope of hydrogen, some hydrogen atoms may be deuterium.

[0037] In one embodiment of the present application, "when no substituent is shown in the chemical formula or compound structure," it means that all positions available as substituents are hydrogen or deuterium. In other words, in the case of deuterium, it is an isotope of hydrogen, and some hydrogen atoms may be deuterium, which is an isotope, and in this case, the content of deuterium may be 0% to 100%. In one embodiment of the present invention, when "substituents are not displayed in the chemical formula or structure of the compound," and deuterium is not explicitly excluded, such as when "the deuterium content is 0%," "the hydrogen content is 100%," or "all substituents are hydrogen," hydrogen and deuterium may be used together in the compound.

[0038] In one embodiment of the present invention, deuterium is one of the isotopes of hydrogen and is an element having a deuteron consisting of one proton and one neutron as an atomic nucleus, and may be represented as hydrogen-2, and its atomic symbol may be D or 2H. In one embodiment of the present invention, isotopes refer to atoms that have the same atomic number (Z) but different mass numbers (A). Isotopes can also be interpreted as elements that have the same number of protons but different numbers of neutrons.

[0039] In one embodiment of the present invention, the content T% of a specific substituent can be defined as T2 / T1×100=T%, where T1 is the total number of substituents that the base compound may have and T2 is the number of specific substituents among them.

[0040] That is, in one example: [ka] A phenyl group represented by the formula (I) having a deuterium content of 20% may mean that the total number of substituents that the phenyl group may have is 5 (T1 in the formula), of which the number of deuterium is 1 (T2 in the formula). That is, a phenyl group having a deuterium content of 20% may be represented by the following structural formula: [ka]

[0041] In addition, in one embodiment of the present invention, a "phenyl group having a deuterium content of 0%" means a phenyl group that does not contain a deuterium atom, that is, a phenyl group that has five hydrogen atoms. In the present invention, the C6 to C60 aromatic hydrocarbon ring refers to a compound containing an aromatic ring consisting of C6 to C60 carbon atoms and hydrogen atoms, and examples thereof include, but are not limited to, benzene, biphenyl, terphenyl, triphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, phyllene, chrysene, ferrylene, and azulene, and include all aromatic hydrocarbon ring compounds known in this field as satisfying the above carbon number.

[0042] In one embodiment of the present application, there is provided a heterocyclic compound represented by the following Chemical Formula 1: [ka]

[0043] In the above Chemical Formula 1, Y1 to Y3 are the same or different and each independently represents CH; or N; At least one of Y1 to Y3 is N, Ar1 and Ar2 are the same or different and each independently represent a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; L1 and L2 are the same or different and each independently represent a single bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group; R1 are the same or different and each independently represent hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or unsubstituted C2 to C60 heterocycloalkyl group; substituted or unsubstituted C6 to C60 aryl group; or substituted or unsubstituted C2 to C60 heteroaryl group; R2 to R9 are the same or different and each independently represent hydrogen; deuterium; a C1 to C60 alkyl group substituted or unsubstituted with deuterium; a C3 to C60 cycloalkyl group substituted or unsubstituted with deuterium; a C2 to C60 heterocycloalkyl group substituted or unsubstituted with deuterium; a C6 to C60 aryl group substituted or unsubstituted with deuterium; or a C2 to C60 heteroaryl group substituted or unsubstituted with deuterium; at least one of R2 to R9 is a deuterium or a C6 to C60 aryl group substituted with deuterium, n1 is an integer from 0 to 8, n2 and n3 are the same or different and each independently represents an integer of 0 to 4, When n1, n2 and n3 are 2 or more, R1, L1 and L2 are the same or different from each other.

[0044] In one embodiment of the present application, Y1 may be N, and Y2 and Y3 may be CH. In yet another embodiment, Y1 and Y2 can be N and Y3 can be CH. In yet another embodiment, Y1 and Y3 can be N and Y2 can be CH. In yet another embodiment, Y 1 can be CH and Y 2 and Y 3 can be N. In yet another embodiment, Y1 and Y2 may be CH and Y3 may be N. In yet another embodiment, Y1 and Y3 may be CH and Y2 may be N. In another embodiment, Y1 to Y3 may be N.

[0045] In one embodiment of the present application, Ar1 and Ar2 are the same or different and may each independently be a substituted or unsubstituted C6 to C40 aryl group or a substituted or unsubstituted C2 to C40 heteroaryl group. In yet another embodiment, Ar1 and Ar2 may be the same or different and may each independently be a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group. In yet another embodiment, Ar1 and Ar2 may be the same or different and may each independently be a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C20 heteroaryl group. In yet another embodiment, Ar1 and Ar2 may be the same or different and may each independently be a substituted or unsubstituted C6 to C10 aryl group or a substituted or unsubstituted C2 to C10 heteroaryl group.

[0046] In yet another embodiment, Ar1 and Ar2 are the same or different and may each independently be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted triphenyl group; a substituted or unsubstituted carbazole group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group.

[0047] In yet another embodiment, Ar1 and Ar2 are the same or different 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 carbazole group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group. In yet another embodiment, Ar1 and Ar2 may be the same or different and may contain no deuterium.

[0048] In one embodiment of the present application, L1 and L2 are the same or different and may each independently be a single bond; a substituted or unsubstituted C6 to C40 arylene group; or a substituted or unsubstituted C2 to C40 heteroarylene group. In yet another embodiment, L1 and L2 are the same or different and may each independently be a single bond; a substituted or unsubstituted C6 to C30 arylene group; or a substituted or unsubstituted C2 to C30 heteroarylene group. In yet another embodiment, L1 and L2 are the same or different and may each independently be a single bond; a substituted or unsubstituted C6 to C20 arylene group; or a substituted or unsubstituted C2 to C20 heteroarylene group. In yet another embodiment, L1 and L2 are the same or different and may each independently be a single bond; a substituted or unsubstituted C6 to C10 arylene group; or a substituted or unsubstituted C2 to C10 heteroarylene group.

[0049] In yet another embodiment, L1 and L2 are the same or different and may each independently be a single bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted naphthylene group; a substituted or unsubstituted terphenylene group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted triphenyl group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted carbazole group; or a substituted or unsubstituted dibenzothiophenyl group.

[0050] In yet another embodiment, L1 and L2 are the same or different and may each independently be a single bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted terphenylene group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group. In another embodiment, L1 and L2 may be the same or different and each may contain no deuterium.

[0051] In one embodiment of the present application, the compound represented by the formula 1 [ka] The deuterium content based on the total number of hydrogen atoms and deuterium atoms in the portion corresponding to may be 100% or less, for example, 100% or less, 95% or less, 90% or less, 85% or less, 80% or less, 75% or less, 70% or less, 65% or less, 60% or less, 55% or less, 50% or less, 45% or less, 40% or less, 35% or less, 30% or less, 25% or less, 20% or less, 15% or less, 10% or less, 5% or less, 4% or less, 3% or less, 2% or less, or 1% or less. * means a portion connected to Chemical Formula 1; Y1 to Y3, Ar1, Ar2, L1, L2, n2, and n3 are defined as in Chemical Formula 1.

[0052] In another embodiment, the compound represented by Chemical Formula 1 [ka] The part corresponding to may have a deuterium content of 0%.

[0053] In one embodiment of the present application, R1 may be the same or different and each independently may be hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to C40 alkyl group; substituted or unsubstituted C3 to C40 cycloalkyl group; substituted or unsubstituted C2 to C40 heterocycloalkyl group; substituted or unsubstituted C6 to C40 aryl group; or substituted or unsubstituted C2 to C40 heteroaryl group.

[0054] In yet another embodiment, R1 may be the same or different and each independently may be hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to C30 alkyl group; substituted or unsubstituted C3 to C30 cycloalkyl group; substituted or unsubstituted C2 to C30 heterocycloalkyl group; substituted or unsubstituted C6 to C30 aryl group; or substituted or unsubstituted C2 to C30 heteroaryl group.

[0055] In yet another embodiment, R1 may be the same or different and each independently may be hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to C20 alkyl group; substituted or unsubstituted C3 to C20 cycloalkyl group; substituted or unsubstituted C2 to C20 heterocycloalkyl group; substituted or unsubstituted C6 to C20 aryl group; or substituted or unsubstituted C2 to C20 heteroaryl group.

[0056] In yet another embodiment, R1 may be the same or different and each independently represent hydrogen; deuterium; halogen; cyano; a substituted or unsubstituted C1-C10 alkyl group; a substituted or unsubstituted C3-C10 cycloalkyl group; a substituted or unsubstituted C2-C10 heterocycloalkyl group; a substituted or unsubstituted C6-C10 aryl group; or a substituted or unsubstituted C2-C10 heteroaryl group.

[0057] In yet another embodiment, R1 may be the same or different and each independently may be hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group. In yet another embodiment, R1 may be the same or different and each independently may be hydrogen; deuterium; a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group. In yet another embodiment, R1 may be the same or different and each independently may be hydrogen; deuterium; a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0058] In yet another embodiment, R1 may be the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group. In yet another embodiment, R1 may be the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted C1-C10 alkyl group; a substituted or unsubstituted C6-C10 aryl group; or a substituted or unsubstituted C2-C10 heteroaryl group. In yet another embodiment, R1 may be the same or different and each independently may be hydrogen; deuterium; a substituted or unsubstituted methyl group; a substituted or unsubstituted butyl group; a substituted or unsubstituted tert-butyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted carbazolyl group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group.

[0059] In one embodiment of the present application, R2 to R9 are the same or different and may each independently represent hydrogen; deuterium; a C1 to C40 alkyl group substituted or unsubstituted with deuterium; a C3 to C40 cycloalkyl group substituted or unsubstituted with deuterium; a C2 to C40 heterocycloalkyl group substituted or unsubstituted with deuterium; a C6 to C40 aryl group substituted or unsubstituted with deuterium; or a C2 to C40 heteroaryl group substituted or unsubstituted with deuterium.

[0060] In yet another embodiment, R2 to R9 are the same or different and may each independently represent hydrogen; deuterium; a C1 to C30 alkyl group substituted or unsubstituted with deuterium; a C3 to C30 cycloalkyl group substituted or unsubstituted with deuterium; a C2 to C30 heterocycloalkyl group substituted or unsubstituted with deuterium; a C6 to C30 aryl group substituted or unsubstituted with deuterium; or a C2 to C30 heteroaryl group substituted or unsubstituted with deuterium.

[0061] In yet another embodiment, R2 to R9 are the same or different and may each independently represent hydrogen; deuterium; a C1 to C20 alkyl group substituted or unsubstituted with deuterium; a C3 to C20 cycloalkyl group substituted or unsubstituted with deuterium; a C2 to C20 heterocycloalkyl group substituted or unsubstituted with deuterium; a C6 to C20 aryl group substituted or unsubstituted with deuterium; or a C2 to C20 heteroaryl group substituted or unsubstituted with deuterium.

[0062] In yet another embodiment, R2 to R9 are the same or different and each independently represent hydrogen; deuterium; a C1 to C10 alkyl group substituted or unsubstituted with deuterium; a C3 to C10 cycloalkyl group substituted or unsubstituted with deuterium; a C2 to C10 heterocycloalkyl group substituted or unsubstituted with deuterium; a C6 to C10 aryl group substituted or unsubstituted with deuterium; or a C2 to C10 heteroaryl group substituted or unsubstituted with deuterium. In yet another embodiment, R2 to R9 may be the same or different and each independently may be hydrogen; deuterium; or a phenyl group unsubstituted or substituted with deuterium.

[0063] In one embodiment of the present invention, at least one of R2 to R9 may be deuterium; or a C6 to C60 aryl group substituted with deuterium. In another embodiment, at least two of R2 to R9 may be deuterium; or a C6 to C60 aryl group substituted with deuterium. In another embodiment, at least three of R2 to R9 may be deuterium; or a C6 to C60 aryl group substituted with deuterium. In another embodiment, at least four of R2 to R9 may be deuterium; or a C6 to C60 aryl group substituted with deuterium.

[0064] In another embodiment, at least five of R2 to R9 may be deuterium; or a C6 to C60 aryl group substituted with deuterium. In another embodiment, at least six of R2 to R9 may be deuterium; or a C6 to C60 aryl group substituted with deuterium. In another embodiment, at least seven of R2 to R9 may be deuterium; or a C6 to C60 aryl group substituted with deuterium. In yet another embodiment, R2 to R9 may each be a deuterium atom or a C6 to C60 aryl group substituted with deuterium.

[0065] In one embodiment of the present invention, at least one of R2 to R9 may be deuterium; or a C6 to C40 aryl group substituted with deuterium. In another embodiment, at least two of R2 to R9 may be deuterium; or a C6 to C40 aryl group substituted with deuterium. In another embodiment, at least three of R2 to R9 may be deuterium; or a C6 to C40 aryl group substituted with deuterium. In another embodiment, at least four of R2 to R9 may be deuterium; or a C6 to C40 aryl group substituted with deuterium.

[0066] In another embodiment, at least five of R2 to R9 may be deuterium; or a C6 to C40 aryl group substituted with deuterium. In another embodiment, at least six of R2 to R9 may be deuterium or a C6 to C40 aryl group substituted with deuterium. In another embodiment, at least seven of R2 to R9 may be deuterium; or a C6 to C40 aryl group substituted with deuterium. In yet another embodiment, R2 to R9 may each be a deuterium atom or a C6 to C40 aryl group substituted with deuterium.

[0067] In one embodiment of the present invention, at least one of R2 to R9 may be deuterium; or a C6 to C30 aryl group substituted with deuterium. In another embodiment, at least two of R2 to R9 may be deuterium; or a C6 to C30 aryl group substituted with deuterium. In another embodiment, at least three of R2 to R9 may be deuterium; or a C6 to C30 aryl group substituted with deuterium. In another embodiment, at least four of R2 to R9 may be deuterium; or a C6 to C30 aryl group substituted with deuterium.

[0068] In another embodiment, at least five of R2 to R9 may be deuterium or a C6 to C30 aryl group substituted with deuterium. In another embodiment, at least six of R2 to R9 may be deuterium; or a C6 to C30 aryl group substituted with deuterium. In another embodiment, at least seven of R2 to R9 may be deuterium or a C6 to C30 aryl group substituted with deuterium. In another embodiment, R2 to R9 may each be a deuterium atom or a C6 to C30 aryl group substituted with deuterium.

[0069] In one embodiment of the present invention, at least one of R2 to R9 may be deuterium; or a C6 to C20 aryl group substituted with deuterium. In another embodiment, at least two of R2 to R9 may be deuterium; or a C6 to C20 aryl group substituted with deuterium. In another embodiment, at least three of R2 to R9 may be deuterium; or a C6 to C20 aryl group substituted with deuterium. In another embodiment, at least four of R2 to R9 may be deuterium; or a C6 to C20 aryl group substituted with deuterium.

[0070] In another embodiment, at least five of R2 to R9 may be deuterium; or a C6 to C20 aryl group substituted with deuterium. In another embodiment, at least six of R2 to R9 may be deuterium; or a C6 to C20 aryl group substituted with deuterium. In another embodiment, at least seven of R2 to R9 may be deuterium; or a C6 to C20 aryl group substituted with deuterium. In yet another embodiment, R2 to R9 may each be a deuterium atom or a C6 to C20 aryl group substituted with deuterium.

[0071] In one embodiment of the present invention, at least one of R2 to R9 may be deuterium; or a C6 to C10 aryl group substituted with deuterium. In another embodiment, at least two of R2 to R9 may be deuterium; or a C6 to C10 aryl group substituted with deuterium. In another embodiment, at least three of R2 to R9 may be deuterium; or a C6 to C10 aryl group substituted with deuterium. In another embodiment, at least four of R2 to R9 may be deuterium; or a C6 to C10 aryl group substituted with deuterium.

[0072] In another embodiment, at least five of R2 to R9 may be deuterium; or a C6 to C10 aryl group substituted with deuterium. In another embodiment, at least six of R2 to R9 may be deuterium; or a C6 to C10 aryl group substituted with deuterium. In another embodiment, at least seven of R2 to R9 may be deuterium; or a C6 to C10 aryl group substituted with deuterium. In yet another embodiment, R2 to R9 may each be a deuterium atom or a C6 to C10 aryl group substituted with deuterium.

[0073] In one embodiment of the present invention, at least one of R2 to R9 may be deuterium; or a phenyl group substituted with deuterium. In another embodiment, at least two of R2 to R9 may be deuterium or a phenyl group substituted with deuterium. In another embodiment, at least three of R2 to R9 may be deuterium or a phenyl group substituted with deuterium. In another embodiment, at least four of R2 to R9 may be deuterium or a phenyl group substituted with deuterium.

[0074] In another embodiment, at least five of R2 to R9 may be deuterium or a phenyl group substituted with deuterium. In another embodiment, at least six of R2 to R9 may be deuterium or a phenyl group substituted with deuterium. In another embodiment, at least seven of R2 to R9 may be deuterium or a phenyl group substituted with deuterium. In yet another embodiment, R2 to R9 may be deuterium or a phenyl group substituted with deuterium.

[0075] In one embodiment of the present invention, at least one of R2 to R9 may be a deuterium atom; a phenyl group substituted with one or more deuterium atoms; a phenyl group substituted with two or more deuterium atoms; a phenyl group substituted with three or more deuterium atoms; a phenyl group substituted with four or more deuterium atoms; or a phenyl group substituted with all deuterium atoms. In yet another embodiment, at least two of R2 to R9 may be deuterium; a phenyl group substituted with one or more deuterium; a phenyl group substituted with two or more deuterium; a phenyl group substituted with three or more deuterium; a phenyl group substituted with four or more deuterium; or a phenyl group all substituted with deuterium.

[0076] In yet another embodiment, at least three of R2 to R9 may be deuterium; a phenyl group substituted with one or more deuterium; a phenyl group substituted with two or more deuterium; a phenyl group substituted with three or more deuterium; a phenyl group substituted with four or more deuterium; or a phenyl group all substituted with deuterium. In yet another embodiment, at least four of R2 to R9 may be deuterium; a phenyl group substituted with one or more deuterium; a phenyl group substituted with two or more deuterium; a phenyl group substituted with three or more deuterium; a phenyl group substituted with four or more deuterium; or a phenyl group all substituted with deuterium.

[0077] In yet another embodiment, at least five of R2 to R9 may be deuterium; a phenyl group substituted with one or more deuterium; a phenyl group substituted with two or more deuterium; a phenyl group substituted with three or more deuterium; a phenyl group substituted with four or more deuterium; or a phenyl group all substituted with deuterium. In yet another embodiment, at least six of R2 to R9 may be deuterium; a phenyl group substituted with one or more deuterium; a phenyl group substituted with two or more deuterium; a phenyl group substituted with three or more deuterium; a phenyl group substituted with four or more deuterium; or a phenyl group all substituted with deuterium.

[0078] In yet another embodiment, at least seven of R2 to R9 may be deuterium; a phenyl group substituted with one or more deuterium; a phenyl group substituted with two or more deuterium; a phenyl group substituted with three or more deuterium; a phenyl group substituted with four or more deuterium; or a phenyl group all substituted with deuterium. In yet another embodiment, R2 to R9 may be deuterium; a phenyl group substituted with one or more deuteriums; a phenyl group substituted with two or more deuteriums; a phenyl group substituted with three or more deuteriums; a phenyl group substituted with four or more deuteriums; or a phenyl group substituted with all deuteriums.

[0079] In one embodiment of the present invention, at least one of R2 to R9 may be deuterium. In another embodiment, at least two of R2 to R9 may be deuterium. In another embodiment, at least three of R2 to R9 may be deuterium. In another embodiment, at least four of R2 to R9 may be deuterium.

[0080] In another embodiment, at least five of R2 to R9 may be deuterium. In another embodiment, at least six of R2 to R9 may be deuterium. In another embodiment, at least seven of R2 to R9 may be deuterium. In another embodiment, R2 to R9 may be deuterium.

[0081] In one embodiment of the present application, the compound represented by the formula 1 [ka] Based on the total number of hydrogen atoms and deuterium atoms in the portion corresponding to the formula (I), the deuterium content may be 1% to 100%, for example, 1% or more, 10% or more, 12.75% or more, 20% or more, 25% or more, 30% or more, 37.5% or more, 40% or more, 50% or more, or 100% or less, 95% or less, 90% or less, 87.5% or less, 85% or less, 80% or less, 75% or less, 70% or less, 65% or less, 62% or less, 60% or less, or 55% or less. * means a moiety linked to Chemical Formula 1; R2 to R9 are defined as in Chemical Formula 1.

[0082] In one embodiment of the present application, Ar1 and Ar2 in Chemical Formula 1 may be represented by any one of Chemical Formulas 1-1 to 1-3 below.

[0083] [ka]

[0084] [ka]

[0085] [ka]

[0086] In the above Chemical Formulas 1-1 to 1-3, X is O or S; Ar3 is a substituted or unsubstituted C6 to C60 aryl group; R10 to R13 are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C2 to C60 alkenyl group, a substituted or unsubstituted C2 to C60 alkynyl group, a substituted or unsubstituted C1 to C60 alkoxy group, a substituted or unsubstituted C3 to C60 cycloalkyl group, a substituted or unsubstituted C2 to C60 heterocycloalkyl group, a substituted or unsubstituted C6 to C60 aryl group, and a substituted or unsubstituted C2 to C60 heteroaryl group, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C60 heterocycle; * is a moiety that is linked to Chemical Formula 1, n4, n6, and n7 are the same or different and each independently represents an integer of 0 to 4; n5 is an integer from 0 to 3, When n4 to n7 are 2 or more, R10 to R13 are the same or different.

[0087] In one embodiment of the present application, X may be O. In yet another embodiment, X may be S.

[0088] In one embodiment of the present application, R10 to R13 are the same or different and each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to C40 alkyl group; substituted or unsubstituted C2 to C40 alkenyl group; substituted or unsubstituted C2 to C40 alkynyl group; substituted or unsubstituted C1 to C40 alkoxy group; substituted or unsubstituted C3 to C40 cycloalkyl group; substituted or unsubstituted C2 to C40 heterocycloalkyl group; substituted or unsubstituted C6 to C40 aryl group; and substituted or unsubstituted C2 to C40 heteroaryl group, or two or more adjacent groups may bond to each other to form a substituted or unsubstituted C6 to C40 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C40 heterocycle.

[0089] In yet another embodiment, R10 to R13 are the same or different and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to C30 alkyl group; substituted or unsubstituted C2 to C30 alkenyl group; substituted or unsubstituted C2 to C30 alkynyl group; substituted or unsubstituted C1 to C30 alkoxy group; substituted or unsubstituted C3 to C30 cycloalkyl group; substituted or unsubstituted C2 to C30 heterocycloalkyl group; substituted or unsubstituted C6 to C30 aryl group; and substituted or unsubstituted C2 to C30 heteroaryl group, or two or more adjacent groups may be bonded to each other to form a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C30 heterocycle.

[0090] In yet another embodiment, R10 to R13 are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C2 to C20 heterocycloalkyl group, a substituted or unsubstituted C6 to C20 aryl group, and a substituted or unsubstituted C2 to C20 heteroaryl group, or two or more adjacent groups may be bonded to each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C20 heterocycle.

[0091] In yet another embodiment, R10 to R13 are the same or different and may each independently be hydrogen; deuterium; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0092] In yet another embodiment, R10 to R13 are the same or different and may each independently be hydrogen; deuterium; a substituted or unsubstituted C6 to C10 aryl group; or a substituted or unsubstituted C2 to C10 heteroaryl group. In yet another embodiment, R10 to R13 may be the same or different and may each independently be hydrogen; deuterium; or a substituted or unsubstituted C6 to C10 aryl group.

[0093] In another embodiment, R10 to R13 may be the same or different and may each independently be hydrogen or a substituted or unsubstituted C6 to C10 aryl group. In yet another embodiment, R10 to R13 are the same or different and may each independently represent a hydrogen atom; 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; or a substituted or unsubstituted triphenyl group.

[0094] In yet another embodiment, R10 to R13 may be the same or different and may each independently be hydrogen; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted naphthyl group. In yet another embodiment, R10 to R13 may be the same or different and may each independently be hydrogen; a substituted or unsubstituted phenyl group; or a substituted or unsubstituted biphenyl group.

[0095] In one embodiment of the present application, Ar3 may be a substituted or unsubstituted C6 to C40 aryl group. In yet another embodiment, Ar3 may be a substituted or unsubstituted C6 to C30 aryl group. In yet another embodiment, Ar3 may be a substituted or unsubstituted C6 to C20 aryl group. In yet another embodiment, Ar3 may be a substituted or unsubstituted C6 to C10 aryl group.

[0096] In yet another embodiment, Ar3 can be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted fluorenyl group; or a substituted or unsubstituted triphenyl group. In yet another embodiment, Ar3 can be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted terphenyl group.

[0097] In one embodiment of the present application, when Ar1 or Ar2 in Chemical Formula 1 is represented by Chemical Formula 1-2, L1 and L2 in Chemical Formula 1 may be the same or different and may each independently be a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group. In another embodiment, when Ar1 or Ar2 in Chemical Formula 1 is represented by Chemical Formula 1-2, L1 and L2 in Chemical Formula 1 may be the same or different and may each independently be a substituted or unsubstituted C6 to C40 arylene group; or a substituted or unsubstituted C2 to C40 heteroarylene group.

[0098] In another embodiment, when Ar1 or Ar2 in Chemical Formula 1 is represented by Chemical Formula 1-2, L1 and L2 in Chemical Formula 1 may be the same or different and may each independently be a substituted or unsubstituted C6 to C30 arylene group; or a substituted or unsubstituted C2 to C30 heteroarylene group. In another embodiment, when Ar1 or Ar2 in Chemical Formula 1 is represented by Chemical Formula 1-2, L1 and L2 in Chemical Formula 1 may be the same or different and may each independently be a substituted or unsubstituted C6 to C20 arylene group; or a substituted or unsubstituted C2 to C20 heteroarylene group.

[0099] In another embodiment, when Ar1 or Ar2 in Chemical Formula 1 is represented by Chemical Formula 1-2, L1 and L2 in Chemical Formula 1 may be the same or different and may each independently be a substituted or unsubstituted C6 to C10 arylene group; or a substituted or unsubstituted C2 to C10 heteroarylene group.

[0100] In yet another embodiment, when Ar1 or Ar2 in Chemical Formula 1 is represented by Chemical Formula 1-2, L1 and L2 in Chemical Formula 1 may be the same or different and may each independently be a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted naphthylene group; a substituted or unsubstituted terphenylene group; a substituted or unsubstituted fluorenylene group; or a substituted or unsubstituted triphenylene group.

[0101] In another embodiment, when Ar1 or Ar2 in Chemical Formula 1 is represented by Chemical Formula 1-2, L1 and L2 in Chemical Formula 1 may be the same or different and may each independently be a substituted or unsubstituted phenylene group; or a substituted or unsubstituted biphenylene group.

[0102] In one embodiment of the present application, the heterocyclic compound represented by Chemical Formula 1 may have a deuterium content of 1% to 100% based on the total number of hydrogen atoms and deuterium atoms. In one embodiment of the present application, the heterocyclic compound represented by Chemical Formula 1 may have a deuterium content of 10% to 100% based on the total number of hydrogen atoms and deuterium atoms.

[0103] In one embodiment of the present application, the heterocyclic compound represented by Chemical Formula 1 may have a deuterium content of 20% to 90% based on the total number of hydrogen atoms and deuterium atoms. In one embodiment of the present application, the heterocyclic compound represented by Chemical Formula 1 may have a deuterium content of 30% to 80% based on the total number of hydrogen atoms and deuterium atoms.

[0104] In one embodiment of the present application, the heterocyclic compound represented by Chemical Formula 1 may have a deuterium content of 40% to 70% based on the total number of hydrogen atoms and deuterium atoms. In one embodiment of the present application, the heterocyclic compound represented by Chemical Formula 1 may have a deuterium content of 40% to 60% based on the total number of hydrogen atoms and deuterium atoms.

[0105] In one embodiment of the present application, the heterocyclic compound represented by Chemical Formula 1 may have a deuterium content of 40% to 50% based on the total number of hydrogen atoms and deuterium atoms.

[0106] In one embodiment of the present specification, the Chemical Formula 1 is represented by any one of the following compounds: [ka]

[0107] [ka]

[0108] [ka]

[0109] [ka]

[0110] [ka]

[0111] [ka]

[0112] [ka]

[0113] [ka]

[0114] Furthermore, by introducing various substituents into the structure of Formula 1, it is possible to synthesize compounds having the unique properties of the introduced substituents. For example, by introducing into the core structure substituents that are primarily used in hole injection layer materials, hole transport materials, light emitting layer materials, electron transport layer materials, and charge generation layer materials used in the manufacture of organic light emitting devices, it is possible to synthesize materials that satisfy the requirements for each organic material layer.

[0115] In addition, by introducing various substituents into the structure of Chemical Formula 1, it is possible to finely adjust the energy band gap, while improving the properties at the interface between organic materials, thereby diversifying the uses of the material.

[0116] Another embodiment of the present invention provides an organic light-emitting device comprising a heterocyclic compound represented by Chemical Formula 1. The "organic light-emitting device" can be expressed by terms such as "organic light-emitting diode," "OLED (Organic Light Emitting Diodes)," "OLED device," "organic electroluminescent device," etc.

[0117] In one embodiment of the present application, there is provided an organic light-emitting device including a first electrode; a second electrode provided opposite the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes a heterocyclic compound represented by Chemical Formula 1.

[0118] In one embodiment of the present application, the first electrode may be a positive electrode and the second electrode may be a negative electrode. In another embodiment, the first electrode may be a negative electrode and the second electrode may be a positive electrode.

[0119] In one embodiment of the present application, the organic light emitting device may be a blue organic light emitting device, and the heterocyclic compound of Formula 1 may be used as a material for the blue organic light emitting device. 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 for the green organic light emitting device.

[0120] 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 for the red organic light emitting device. In one embodiment of the present application, the organic light emitting device may be a blue organic light emitting device, and the heterocyclic compound of Formula 1 may be used as a light emitting layer material of the blue organic light emitting device.

[0121] 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 for the light emitting layer of the green organic light emitting device. 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 for the light emitting layer of the red organic light emitting device.

[0122] The specific details of the heterocyclic compound represented by Chemical Formula 1 are as described above. The organic light emitting device of the present invention can be manufactured using a conventional method and materials for manufacturing an organic light emitting device, except that one or more organic material layers are formed using the heterocyclic compound described above.

[0123] The heterocyclic compound may be formed in an organic layer by a solution coating method as well as a vacuum deposition method during fabrication of an organic light emitting device, including, but not limited to, spin coating, deep coating, inkjet printing, screen printing, spraying, and roll coating.

[0124] The organic material layer of the organic light-emitting device of the present invention may have a single-layer structure, or may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as the organic material layer. However, the structure of the organic light-emitting device is not limited thereto, and the device may include a fewer number of organic material layers.

[0125] In particular, the heterocyclic compound represented by Chemical Formula 1 has a structural feature including a hexagonal heterocycle including Y1 to Y3, which functions as a strong electron acceptor and is responsible for the LUMO (Lowest Unoccupied Molecular Orbital) in the molecule, thereby effectively attracting electrons and stabilizing them in the molecule, thereby improving the lifespan of the device.

[0126] In addition, the compound of Formula 1 has a structural feature including a carbazole-based heterocyclic functional group that functions as a strong electron donor and is responsible for the HOMO (Highest Occupied Molecular Orbital) within the molecule, which results in high hole mobility and smooth intramolecular charge transfer, allowing for low drive and high efficiency.

[0127] In addition, the carbazole-based heterocycle of Formula 1 has a structural feature in which a biphenyl group is substituted at the ortho position, which causes steric hindrance in space, increasing spatial charge mobility and achieving high luminous efficiency while also improving lifetime characteristics.

[0128] In addition, the heterocyclic compound represented by Chemical Formula 1 has a structural feature in which the biphenyl group between the hexagonal heterocycle containing Y1 to Y3 and the carbazole-based heterocyclic functional group is substituted with at least one deuterium atom, and since the carbon-deuterium bond length is shorter than the carbon-hydrogen bond length, the van der Waals forces generated between the molecules are weak, resulting in weak intermolecular interactions. As a result, the volume of the thin film of the device increases and the crystallinity of the thin film decreases, thereby improving the device's lifespan.

[0129] Therefore, when the compound represented by Formula 1 is used in an organic material layer, the driving voltage of the organic light emitting device is reduced, the luminous efficiency is increased, and the life characteristics of the organic light emitting device are improved due to the thermal stability of the compound.

[0130] In the organic light-emitting device of the present invention, the organic material layer may include a light-emitting layer, and the light-emitting layer may include a heterocyclic compound represented by Chemical Formula 1 above. In the organic light-emitting device of the present invention, the organic material layer may include a light-emitting layer, and the light-emitting layer may include the heterocyclic compound represented by Chemical Formula 1 as a light-emitting layer host.

[0131] In another embodiment of the present invention, the organic light-emitting device may further include one or more layers selected from the group consisting of an emitting layer, a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron injection layer, an electron transport layer, a cell blocking layer, and a hole blocking layer. In one embodiment of the present invention, the organic light-emitting device includes one or more organic layers, and the organic layers include a hole transport layer, and the hole transport layer can include a heterocyclic compound represented by Chemical Formula 1. In one embodiment of the present invention, the organic light-emitting device includes one or more organic layers, and the organic layers include a hole transport auxiliary layer, and the hole transport auxiliary layer can include a heterocyclic compound represented by Chemical Formula 1.

[0132] In one embodiment of the present invention, the organic layer contains the heterocyclic compound represented by Chemical Formula 1, and may be used together with a phosphorescent dopant. The phosphorescent dopant material may be any material known in the art, such as LL'MX', LL'L"M, LMX'X", L2MX', and L3M, but these examples do not limit the scope of the present invention.

[0133] The M may be iridium, platinum, osmium, or the like. The L is sp 2 X is an anionic bidentate ligand coordinated to M by carbon and heteroatoms, and X can function as an electron or hole trap. Non-limiting examples of L, L', and L" include 2-(1-naphthyl)benzoxazole, 2-phenylbenzoxazole, 2-phenylbenzothiazole, 7,8-benzoquinoline, phenylpyridine, benzothiophene pyridine, 3-methoxy-2-phenylpyridine, thiophene pyridine, and tolylpyridine. Non-limiting examples of X' and X" include acetylacetonate (acac), hexafluoroacetylacetonate, salicylidene, picolinate, and 8-hydroxyquinolinate.

[0134] Specific examples of the phosphorescent dopant include, but are not limited to, the following: [ka]

[0135] In one embodiment of the present invention, the organic layer contains the heterocyclic compound represented by Chemical Formula 1, and may be used together with an iridium-based dopant. In one embodiment of the present invention, the iridium-based dopant may be (piq)2(Ir)(acac), which is a red phosphorescent dopant. In one embodiment of the present invention, the iridium-based dopant may be Ir(ppy)3, which is a green phosphorescent dopant.

[0136] In one embodiment of the present invention, the content of the dopant may be 1% to 15%, preferably 2% to 10%, and more preferably 3% to 7% based on the weight of the entire light-emitting layer.

[0137] In the organic light-emitting device according to one embodiment of the present invention, the organic material layer may include a hole transport layer or a hole transport assisting layer, and the hole transport layer or the hole transport assisting layer may include a heterocyclic compound represented by Chemical Formula 1. In the organic light emitting device according to another embodiment of the present invention, the organic material layer may include an electron injection layer or an electron transport layer, and the electron injection layer or the electron transport layer may include a heterocyclic compound represented by Chemical Formula 1.

[0138] In the organic light emitting device according to another embodiment of the present invention, the organic material layer may include an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer may include a heterocyclic compound represented by Chemical Formula 1. In the organic light-emitting device according to another embodiment of the present invention, the organic material layer may include 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 a heterocyclic compound represented by Chemical Formula 1.

[0139] In the organic light emitting device according to another embodiment of the present invention, the organic material layer may include an emitting layer, and the emitting layer may include the heterocyclic compound represented by Chemical Formula 1 above. In the organic light emitting device according to another embodiment of the present invention, the organic material layer may include an emitting layer, the emitting layer may include a host material, and the host material may include a heterocyclic compound represented by Chemical Formula 1.

[0140] In another embodiment of the organic light emitting device, the light emitting layer may include two or more host materials, and at least one of the host materials may include a heterocyclic compound represented by Chemical Formula 1.

[0141] In another embodiment of the organic light emitting device, the light emitting layer may be a pre-mixed mixture of two or more host materials, and at least one of the two or more host materials may include a heterocyclic compound represented by Chemical Formula 1.

[0142] The term "pre-mixed" means that the light-emitting layer is prepared by mixing two or more host materials in a single supply source before depositing the materials on the organic layer.

[0143] In an organic light-emitting device according to an embodiment of the present application, the organic material layer containing the heterocyclic compound represented by Chemical Formula 1 further contains a heterocyclic compound represented by Chemical Formula 2 or Chemical Formula 3:

[0144] [ka]

[0145] [ka]

[0146] In the above Chemical Formula 2 and Chemical Formula 3, L3 to L7 are the same or different and each independently represent a single bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group; Ar4 to Ar7 are the same or different and each independently represent a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, R15 to R19 are the same or different and each independently represent hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C2 to C60 alkenyl group; substituted or unsubstituted C2 to C60 alkynyl group; substituted or unsubstituted C1 to C60 alkoxy group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or unsubstituted C2 to C60 heterocycloalkyl group; substituted or unsubstituted C6 to C60 aryl group; or substituted or unsubstituted C2 to C60 heteroaryl. or -SiR101R102R103; or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same or different and each independently represent a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, m1 to m5 are the same or different and each independently represents an integer of 0 to 3, e and f are the same or different and each independently represents an integer of 0 to 7; g and h are the same or different and each independently represents an integer of 0 to 4, i is an integer from 0 to 2, When m1 to m5, e, f, g, h, and i are 2 or more, L3 to L7 and R15 to R19 are the same as or different from each other.

[0147] When the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2 or Chemical Formula 3 are contained in the organic material layer of an organic light emitting device, the organic light emitting device exhibits better efficiency and lifespan. This result suggests that an exciplex phenomenon occurs when the two compounds are contained together.

[0148] The exciplex phenomenon is a phenomenon in which electron exchange between two molecules releases energy equivalent to the HOMO level of the donor (p-host) and the LUMO level of the acceptor (n-host). When the exciplex phenomenon occurs between two molecules, reverse intersystem crossing (RISC) occurs, which increases the internal quantum efficiency of fluorescence to 100%. When a donor (p-host) with good hole transporting ability and an acceptor (n-host) with good electron transporting ability are used as the host of the emitting layer, holes are injected into the p-host and electrons are injected into the n-host, which reduces the driving voltage and improves the lifetime.

[0149] In particular, the heterocyclic compound represented by Chemical Formula 1 has a structural feature including a hexagonal heterocycle including Y1 to Y3, which acts as a strong electron acceptor and is responsible for the LUMO (Lowest Unoccupied Molecular Orbital) in the molecule, thereby effectively attracting electrons and stabilizing electrons in the molecule, thereby improving the lifespan of the device.

[0150] In addition, the compound of Formula 1 has a structural feature including a carbazole-based heterocyclic functional group that acts as a strong electron donor and is responsible for the HOMO (Highest Occupied Molecular Orbital) within the molecule, which allows it to have high hole mobility and smooth intramolecular charge transfer, resulting in low drive and high efficiency.

[0151] In addition, the carbazole-based heterocycle of Formula 1 has a structural feature in which a biphenyl group is substituted at the ortho position, which causes steric hindrance in space, increasing spatial charge mobility and improving luminous efficiency and lifetime characteristics.

[0152] In addition, the heterocyclic compound represented by Chemical Formula 1 has a structural feature in which the biphenyl group between the hexagonal heterocycle containing Y1 to Y3 and the carbazole-based heterocyclic functional group is substituted with at least one deuterium atom, and since the carbon-deuterium bond length is shorter than the carbon-hydrogen bond length, the van der Waals forces generated between the molecules are weaker, resulting in weaker intermolecular interactions. This results in an increase in the volume of the thin film of the device and a decrease in the crystallinity of the thin film, thereby improving the device's lifespan.

[0153] Therefore, when the compound represented by Formula 1 is used in an organic material layer, the driving voltage of the organic light emitting device is reduced, the luminous efficiency is increased, and the life characteristics of the organic light emitting device are improved due to the thermal stability of the compound.

[0154] In one embodiment of the present application, L3 to L7 are the same or different and may each independently be a single bond; a substituted or unsubstituted C6 to C40 arylene group; or a substituted or unsubstituted C2 to C40 heteroarylene group. In yet another embodiment, L3 to L7 are the same or different and may each independently be a single bond; a substituted or unsubstituted C6 to C30 arylene group; or a substituted or unsubstituted C2 to C30 heteroarylene group.

[0155] In yet another embodiment, L3 to L7 are the same or different and may each independently be a single bond; a substituted or unsubstituted C6 to C20 arylene group; or a substituted or unsubstituted C2 to C20 heteroarylene group. In yet another embodiment, L3 to L7 are the same or different and may each independently be a single bond; a substituted or unsubstituted C6 to C10 arylene group; or a substituted or unsubstituted C2 to C10 heteroarylene group.

[0156] In yet another embodiment, L3 to L7 are the same or different and may each independently represent a single bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted terphenylene group; a substituted or unsubstituted naphthylene group; a substituted or unsubstituted fluorene group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenylene group.

[0157] In yet another embodiment, L3 to L7 are the same or different and may each independently represent a single bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted fluorene group; or a substituted or unsubstituted dibenzofuranyl group.

[0158] In one embodiment of the present application, Ar4 to Ar7 may be the same or different, and each may independently be a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group. In yet another embodiment, Ar4 to Ar7 may be the same or different and each independently may be a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0159] In yet another embodiment, Ar4 to Ar7 may be the same or different and each independently may be a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group. In yet another embodiment, Ar4 to Ar7 may be the same or different and each independently may be a substituted or unsubstituted C6 to C10 aryl group; or a substituted or unsubstituted C2 to C10 heteroaryl group.

[0160] In yet another embodiment, Ar4 to Ar7 are the same or different and may each independently represent 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 triphenyl group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted dibenzothiophenyl group; or a substituted or unsubstituted tetraphenylsilanyl group.

[0161] In one embodiment of the present application, R15 to R19 are the same or different and each independently represent hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to C40 alkyl group; substituted or unsubstituted C2 to C40 alkenyl group; substituted or unsubstituted C2 to C40 alkynyl group; substituted or unsubstituted C1 to C40 alkoxy group; substituted or unsubstituted C3 to C40 cycloalkyl group; substituted or unsubstituted C2 to C40 heterocycloalkyl group; substituted or unsubstituted C6 to C40 aryl group; or -SiR101R102R103, or two or more adjacent groups bond to each other to form a substituted or unsubstituted C6 to C40 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C40 heterocycle, wherein R101, R102, and R103 may be the same or different and each independently a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0162] In still another embodiment, R15 to R19 are the same or different and each independently represent hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to C30 alkyl group; substituted or unsubstituted C2 to C30 alkenyl group; substituted or unsubstituted C2 to C30 alkynyl group; substituted or unsubstituted C1 to C30 alkoxy group; substituted or unsubstituted C3 to C30 cycloalkyl group; substituted or unsubstituted C2 to C30 heterocycloalkyl group; substituted or unsubstituted C6 to C30 aryl group; or -SiR101R102R103, or two or more adjacent groups bond together to form a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C30 heterocycle, wherein R101, R102, and R103 may be the same or different and each independently represent a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0163] In yet another embodiment, R15 to R19 are the same or different and each independently selected from the group consisting of hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C2 to C20 heterocycloalkyl group, a substituted or unsubstituted C6 to C20 aryl group, and a substituted or unsubstituted C2 to C20 heteroaryl group, or two or more adjacent groups may bond to each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C20 heterocycle.

[0164] In yet another embodiment, R15 to R19 are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C2 to C10 alkenyl group, a substituted or unsubstituted C2 to C10 alkynyl group, a substituted or unsubstituted C1 to C10 alkoxy group, a substituted or unsubstituted C3 to C10 cycloalkyl group, a substituted or unsubstituted C2 to C10 heterocycloalkyl group, a substituted or unsubstituted C6 to C10 aryl group, and a substituted or unsubstituted C2 to C10 heteroaryl group, or two or more adjacent groups may be bonded to each other to form a substituted or unsubstituted C6 to C10 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C10 heterocycle.

[0165] In yet another embodiment, R15 to R19 are the same or different and may each independently be hydrogen; deuterium; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted terphenyl group.

[0166] In another embodiment, R15 to R19 may be the same or different and may each independently be hydrogen or deuterium.

[0167] In one embodiment of the present application, Ar4 to Ar7 may be represented by any one of the following chemical formulas 2-1 and 2-2.

[0168] [ka]

[0169] [ka]

[0170] In the above Chemical Formula 2-1 and Chemical Formula 2-2, X3 is O; S; or CRaRb; Ar8 is a substituted or unsubstituted C6-C60 aryl group; R20, R21, Ra, and Rb are the same or different and each independently represent hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C2 to C60 alkenyl group; substituted or unsubstituted C2 to C60 alkynyl group; substituted or unsubstituted C1 to C60 alkoxy group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or unsubstituted C2 to C60 heterocycloalkyl group; substituted or unsubstituted C6 to C60 aryl group; substituted or unsubstituted C2 to C60 hetero an aryl group; -P(=O)R101R102; and -SiR101R102R103, or two or more adjacent groups bond to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102, and R103 are the same or different and each independently represent a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; * is a moiety linked to Chemical Formula 2 or Chemical Formula 3, j is an integer from 0 to 4, k is an integer from 0 to 3, When j and k are 2 or more, R20 and R21 are the same or different.

[0171] In one embodiment of the present application, X3 may be O. In yet another embodiment, X3 may be S. In yet another embodiment, X3 can be CRaRb.

[0172] In one embodiment of the present application, Ar8 may be a substituted or unsubstituted C6 to C40 aryl group. In yet another embodiment, Ar8 can be a substituted or unsubstituted C6 to C30 aryl group.

[0173] In yet another embodiment, Ar8 can be a substituted or unsubstituted C6 to C20 aryl group. In yet another embodiment, Ar8 can be a substituted or unsubstituted C6 to C10 aryl group.

[0174] In yet another embodiment, Ar8 may be selected from among 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; or a substituted or unsubstituted triphenyl group.

[0175] In one embodiment of the present application, R20, R21, Ra and Rb are the same or different and each independently represent hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to C40 alkyl group; substituted or unsubstituted C2 to C40 alkenyl group; substituted or unsubstituted C2 to C40 alkynyl group; substituted or unsubstituted C1 to C40 alkoxy group; substituted or unsubstituted C3 to C40 cycloalkyl group; or -SiR101R102R103, or two or more adjacent groups may be bonded to each other to form a substituted or unsubstituted C6 to C40 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C40 heterocycle, wherein R101, R102, and R103 may be the same or different and each independently represent a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0176] In yet another embodiment, R20, R21, Ra, and Rb are the same or different and each independently represent hydrogen; deuterium; a halogen; a cyano group; a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C2 to C30 alkenyl group; a substituted or unsubstituted C2 to C30 alkynyl group; a substituted or unsubstituted C1 to C30 alkoxy group; a substituted or unsubstituted C3 to C30 cycloalkyl group; or -SiR101R102R103, or two or more adjacent groups may be bonded to each other to form a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C30 heterocycle, wherein R101, R102, and R103 may be the same or different and each independently represent a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0177] In yet another embodiment, R20, R21, Ra, and Rb are the same or different and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to C20 alkyl group; substituted or unsubstituted C2 to C20 alkenyl group; substituted or unsubstituted C2 to C20 alkynyl group; substituted or unsubstituted C1 to C20 alkoxy group; substituted or unsubstituted C3 to C20 cycloalkyl group; substituted or unsubstituted C2 to C20 heterocycloalkyl group; substituted or unsubstituted C6 to C20 aryl group; and substituted or unsubstituted C2 to C20 heteroaryl group, or two or more adjacent groups may be bonded to each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C20 heterocycle.

[0178] In yet another embodiment, R20, R21, Ra, and Rb are the same or different and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to C10 alkyl group; substituted or unsubstituted C2 to C10 alkenyl group; substituted or unsubstituted C2 to C10 alkynyl group; substituted or unsubstituted C1 to C10 alkoxy group; substituted or unsubstituted C3 to C10 cycloalkyl group; substituted or unsubstituted C2 to C10 heterocycloalkyl group; substituted or unsubstituted C6 to C10 aryl group; and substituted or unsubstituted C2 to C10 heteroaryl group, or two or more adjacent groups can be bonded to each other to form a substituted or unsubstituted C6 to C10 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C10 heterocycle.

[0179] In yet another embodiment, R20, R21, Ra, and Rb are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted methyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; 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 pyrenyl group; a substituted or unsubstituted chrysenyl group; a substituted or unsubstituted fluoranthenyl 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; a substituted or unsubstituted triphenylsilanyl group; or a substituted or unsubstituted tetraphenylsilanyl group, or two or more adjacent groups may be bonded to each other to form a substituted or unsubstituted spirobifluorenyl group.

[0180] In yet another embodiment, R20, R21, Ra, and Rb are the same or different and may each independently be hydrogen; deuterium; a substituted or unsubstituted methyl group; a substituted or unsubstituted phenyl group; or a substituted or unsubstituted fluorenyl group.

[0181] In one embodiment of the present application, the heterocyclic compound represented by Chemical Formula 3 may be represented by any one of Chemical Formulas 3-1 to 3-5 below.

[0182] [ka]

[0183] [ka]

[0184] [ka]

[0185] [ka]

[0186] [ka]

[0187] In the above Chemical Formulas 3-1 to 3-5, The definitions of R17 to R19, L6, L7, Ar6, Ar7, g to i, m4, and m5 are the same as those in Chemical Formula 3.

[0188] In one embodiment of the present application, the heterocyclic compound represented by Chemical Formula 2 or Chemical Formula 3 may not contain deuterium as a substituent, and the deuterium content based on the total number of hydrogen atoms and deuterium atoms may be, for example, 1% or more, 5% or more, 10% or more, 15% or more, 20% or more, 25% or more, 30% or more, 35% or more, 40% or more, 45% or more, or 50% or more, or 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.

[0189] In one embodiment of the present application, the heterocyclic compound represented by Chemical Formula 2 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. In one embodiment of the present application, the heterocyclic compound represented by Chemical Formula 2 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. In one embodiment of the present application, the heterocyclic compound represented by Chemical Formula 2 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.

[0190] In one embodiment of the present application, the heterocyclic compound represented by Chemical Formula 2 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. In one embodiment of the present application, the heterocyclic compound represented by Chemical Formula 2 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. In one embodiment of the present application, the heterocyclic compound represented by Chemical Formula 2 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.

[0191] In one embodiment of the present application, the heterocyclic compound represented by Chemical Formula 3 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. In one embodiment of the present application, the heterocyclic compound represented by Chemical Formula 3 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. In one embodiment of the present application, the heterocyclic compound represented by Chemical Formula 3 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.

[0192] In one embodiment of the present application, the heterocyclic compound represented by Chemical Formula 3 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. In one embodiment of the present application, the heterocyclic compound represented by Chemical Formula 3 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. In one embodiment of the present application, the heterocyclic compound represented by Chemical Formula 3 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.

[0193] In one embodiment of the present application, there is provided a heterocyclic compound represented by any one of the following compounds, wherein Chemical Formula 2 is: In addition, in one embodiment of the present application, the following compound is an example, and may include other compounds within Chemical Formula 2 that contain additional substituents.

[0194] [ka]

[0195] [ka]

[0196] [ka]

[0197] [ka]

[0198] [ka]

[0199] [ka]

[0200] In one embodiment of the present application, there is provided a heterocyclic compound represented by any one of the following compounds, wherein Chemical Formula 3 is: In addition, in one embodiment of the present application, the following compound is an example, and is not limited to this, and may include other compounds included in Chemical Formula 3 that contain additional substituents.

[0201] [ka]

[0202] [ka]

[0203] [ka]

[0204] [ka]

[0205] [ka]

[0206] [ka]

[0207] [ka]

[0208] Another embodiment of the present application provides a composition for an organic layer, comprising the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2 or Chemical Formula 3. The heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2 or Chemical Formula 3 are as described above.

[0209] The weight ratio of the heterocyclic compound represented by Chemical Formula 1 to the heterocyclic compound represented by Chemical Formula 2 or Chemical Formula 3 in the composition may be, but is not limited to, 1:10 to 10:1, 1:8 to 8:1, 1:5 to 5:1, or 1:2 to 2:1.

[0210] The composition can be used to form an organic material of an organic light-emitting device, and is particularly preferably used to form a host for the light-emitting layer.

[0211] The composition is a simple mixture of two or more compounds, and may be a mixture of powder materials before forming an organic layer of an organic light-emitting device, or a mixture of compounds that are in a liquid state at a suitable temperature or higher. The composition is in a solid state below the melting point of each material, and can be maintained in a liquid state by adjusting the temperature.

[0212] The composition may further include materials known in the art, such as solvents and additives.

[0213] The organic light emitting device according to one embodiment of the present application may be manufactured using a conventional method and materials for manufacturing an organic light emitting device, except that one or more organic material layers are formed using the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2 or Chemical Formula 3.

[0214] The compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2 or Chemical Formula 3 can be formed into an organic material layer by a solution coating method as well as a vacuum deposition method during fabrication of an organic light emitting device, where the solution coating method refers to, but is not limited to, spin coating, deep coating, inkjet printing, screen printing, spraying, roll coating, etc.

[0215] The organic material layer of the organic light-emitting device of the present invention may have a single-layer structure, or may have a multi-layer structure in which two or more organic material layers are laminated. For example, the organic light-emitting device of the present invention has 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 the device may include a fewer number of organic material layers.

[0216] In one embodiment of the present application, the organic light-emitting device may be a blue organic light-emitting device, and the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2 or Chemical Formula 3 may be used as materials for the blue organic light-emitting device. 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 2 or Chemical Formula 3 may be used as materials for the green organic light-emitting device. 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 2 or Chemical Formula 3 may be used as materials for the red organic light emitting device.

[0217] The organic light-emitting device of the present invention may further include one or more layers selected from the group consisting of a light-emitting layer, a hole-injection layer, a hole-transport layer, a hole-transport auxiliary layer, an electron-injection layer, an electron-transport layer, an electron-blocking layer, and a hole-blocking layer. In one embodiment of the present application, there is provided an organic light-emitting device, wherein the organic material layer includes at least one layer selected from the group consisting of a hole-blocking layer, an electron-injecting layer, and an electron-transporting layer, and at least one layer selected from the group consisting of the hole-blocking layer, the electron-injecting layer, and the electron-transporting layer includes the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2 or Chemical Formula 3.

[0218] In one embodiment of the present application, there is provided an organic light-emitting device, wherein the organic material layer includes an emitting layer, and the emitting layer includes the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2 or Chemical Formula 3. In one embodiment of the present application, there is provided an organic light-emitting device, wherein the organic material layer includes an emitting layer, the emitting layer includes a host material, and the host material includes the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2 or Chemical Formula 3.

[0219] 1 to 3 illustrate examples of the stacking order of electrodes and organic layers of an organic light-emitting device according to one embodiment of the present invention. However, these drawings do not limit the scope of the present application, and structures of organic light-emitting devices known in the art may also be applied to the present application. 1 shows an organic light emitting device in which an anode (200), an organic material layer (300), and an anode (400) are sequentially stacked on a substrate (100). However, the present invention is not limited to this structure, and an organic light emitting device in which an anode, an organic material layer, and an anode are sequentially stacked on a substrate, as shown in FIG. Figure 3 shows a case where the organic material layer is multi-layered. The organic light emitting device shown in Figure 3 includes a hole injection layer (301), a hole transport layer (302), an 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 this stacked structure. If necessary, the remaining layers except for the emitting layer may be omitted, and other necessary functional layers may be further added.

[0220] In one embodiment of the present invention, there is provided a method for manufacturing an organic light-emitting device, the method including the steps of: 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 layers, wherein the step of forming the organic material layers includes forming one or more organic material layers using a composition for an organic material layer according to one embodiment of the present invention.

[0221] In one embodiment of the present invention, the step of forming the organic layer comprises pre-mixing the heterocyclic compound represented by Chemical Formula 1 and forming the organic layer using a thermal vacuum deposition method. The term "pre-mixed" means that the heterocyclic compound represented by Formula 1 is mixed in a single supply source before being deposited on the organic layer.

[0222] The premixed materials are referred to as an organic layer composition according to one embodiment of the present application. The organic layer containing the heterocyclic compound represented by Chemical Formula 1 may further contain other materials as needed.

[0223] In an organic light-emitting device according to one embodiment of the present invention, materials other than the heterocyclic compound represented by Chemical Formula 1 are exemplified below. However, these are for illustrative purposes only and are not intended to limit the scope of the present application, and may be substituted with materials known in the art.

[0224] The positive electrode material may be a material with a relatively large work function, such as a conductive transparent oxide, a metal, or a conductive polymer. Specific examples of the positive electrode material include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

[0225] The negative electrode material may be a material with a relatively low work function, such as a metal, a metal oxide, or a conductive polymer. Specific examples of the negative electrode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; and multilayer structures such as LiF / Al or LiO / Al.

[0226] As the hole injection layer material, well-known hole injection layer materials may be used, for example, phthalocyanine compounds such as copper phthalocyanine disclosed in U.S. Pat. No. 4,356,429 or starburst-type amine derivatives described in the literature [Advanced Material, 6, p. 677 (1994)], such as tris(4-carbazol-9-ylphenyl)amine (TCTA), 4,4′,4″-tri[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB), soluble conductive polymer polyaniline / dodecylbenzenesulfonic acid (Polyaniline / Dodecylbenzenesulfonic acid), Poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate), polyaniline / Camphor sulfonic acid, or polyaniline / Poly(4-styrenesulfonate), etc. may also be used.

[0227] As the hole transport layer material, a pyrazoline derivative, an arylamine derivative, a stilbene derivative, a triphenyldiamine derivative, or the like may be used, and a low molecular weight or high molecular weight material may also be used.

[0228] Examples of materials for the electron transport layer include oxadiazole derivatives, anthraquinodimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinodimethane and its derivatives, fluorenone derivatives, diphenyldicyanoethylene and its derivatives, diphenoquinone derivatives, and metal complexes of 8-hydroxyquinoline and its derivatives. Not only low molecular weight substances but also high molecular weight substances may be used.

[0229] As the material for the electron injection layer, for example, LiF is typically used in the industry, but the present application is not limited thereto.

[0230] The emitting layer material may be a red, green, or blue emitting material, or a mixture of two or more emitting materials may be used if necessary. In this case, the two or more emitting materials may be deposited in separate supply sources or premixed and deposited in a single supply source. The emitting layer material may be a fluorescent material or a phosphorescent material. The emitting layer material may be a material that emits light by combining holes and electrons injected from the anode and cathode, respectively, or a material in which both the host material and the dopant material contribute to light emission.

[0231] When a mixture of hosts is used as the material for the light-emitting layer, the mixture may be of the same type or different types. For example, two or more materials selected from n-type host materials or p-type host materials can be used as the host material for the light-emitting layer.

[0232] The organic light emitting device according to an embodiment of the present invention may be a top-emitting type, a back-emitting type, or a double-sided emitting type depending on the materials used. The heterocyclic compound according to one embodiment of the present invention also functions in organic electronic devices such as organic solar cells, organic photoreceptors, and organic transistors in the same manner as in organic light-emitting devices.

[0233] Preferred examples are shown below to aid in understanding the present invention. However, the following examples are provided only to facilitate understanding of the present invention, and the present invention is not limited thereto.

[0234] <Production example> <Production Example 1> Production of Compound 1-1 [ka]

[0235] 1) Preparation of Compound 1-1-P3 10 g (48.4 mmol) of 1-1-P4 was dissolved in 500 mL of Benzene-d6, then dissolved in 123 g (822.7 mmol) of CFSOH and refluxed at 60°C for 1 hour. Upon completion of the reaction, the mixture was neutralized with D2O and Na2CO3. After neutralization, the mixture was extracted with distilled water and ethyl acetate. The organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM (Dichlorometane):Hexane) = 1:4) and purified with methanol to obtain 9.56 g (92%) of the target compound 1-1-P3.

[0236] 1-1) Preparation of Compound 1-1-C 10 g (59.8 mmol) of 9H-carbazole [A] was dissolved in 500 mL of Benzene-d6, then dissolved in 153 g (1017 mmol) of CF3SO3H and refluxed at 60 °C for 1 hour. Upon completion of the reaction, the mixture was neutralized with DO and Na2CO3. After neutralization, the mixture was extracted with distilled water and ethyl acetate. The organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex = 1:4) and purified with methanol to yield 9.85 g (94%) of the desired compound 1-1-C.

[0237] 2) Preparation of Compound 1-1-P2 9.56 g (44.5 mmol) of 1-1-P3 and 7.80 g (44.5 mmol) of 1-1-C were dissolved in 95 mL of DMA (dimethylacetamide), and then 14.5 g (44.5 mmol) of CsCO was added and refluxed at 180 °C for 3 hours. After the reaction was completed, a solid was obtained using HO. The solid compound was purified by column chromatography (DCM:Hex = 1:2) and extracted with methanol to obtain 12.6 g (76.4%) of the target compound 1-1-P2.

[0238] 3) Preparation of Compound 1-1-P1 Compound 1-1-P2 (12.6 g, 34.1 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (13.0 g, 51.15 mmol), Pd2(dba)3 (Tris(dibenzylideneacetone)dipalladium(0)) (1.97 g, 1.71 mmol), Sphos(2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl) (1.40 g, 3.41 mmol), and KOAc (potassium acetate) (6.62 g, 68.2 mmol) were dissolved in 120 mL of 1,4-dioxane and refluxed with stirring for 6 hours. After the reaction was completed, the mixture was extracted with distilled water and DCM at room temperature. The organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex=1:2) to obtain 15.1 g (96.2%) of the target compound 1-1-P1.

[0239] 4) Preparation of Compound 1-1 The compound 1-1-P1 (15.1 g, 32.7 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (8.75 g, 32.7 mmol), Pd(PPh3) (1.89 g, 1.64 mmol), and K2CO3 (9.04 g, 65.4 mmol) were dissolved in 1,4-dioxane / HO (150 mL / 45 mL) and refluxed for 24 hours. After completion of the reaction, the mixture was extracted with distilled water and DCM at room temperature. The organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reaction mixture was purified by column chromatography (DCM:Hex = 1:3) and recrystallized from methanol to yield 16.3 g (88%) of the target compound 1-1.

[0240] <Preparation Example 2> Preparation of Compounds 1-4, 1-9, 1-13, 1-15, 1-25, 1-29, 1-32, 1-34, 1-43, 1-45, 1-49, 1-56, 1-57, 1-59, 1-61, 1-62, 1-63, 1-69, 1-77, 1-78, 1-86 and 1-115 The target compound was synthesized in the same manner as in Preparation Example 1, except that Intermediate A in Table 1 below was used instead of 9H-carbazole and Intermediate B was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0241] [Table 1A]

[0242] [Table 1B]

[0243] [Table 1C]

[0244] [Table 1D]

[0245] <Production Example 3> Production of Compound 1-76 [ka]

[0246] 1) Preparation of Compound 1-76-P3 10 g (48.4 mmol) of the 1-76-P4 was dissolved in 100 mL of Benzene-d6, then dissolved in 25 g (165 mmol) of CF3SO3H and refluxed at 60°C for 1 hour. After completion of the reaction, the mixture was neutralized with D2O and Na2CO3. After neutralization, the mixture was extracted with distilled water and ethyl acetate. The organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex=1:4) and purified with methanol to obtain 9.30 g (91.2%) of the target compound 1-76-P3.

[0247] 2) Preparation of Compound 1-76-P2 9.3 g (44.1 mmol) of the 1-76-P3 and 7.58 g (44.1 mmol) of 9H-carbazole were dissolved in 95 mL of DMA, followed by the addition of 14.1 g (44.5 mmol) of CsCO and refluxing at 180 °C for 3 hours. After the reaction was complete, a solid was obtained using HO. The solid compound was purified by column chromatography (DCM:Hex = 1:2) and added to methanol to obtain 11.9 g (75.5%) of the target compound 1-76-P2.

[0248] 3) Preparation of Compound 1-76-P1 Compound 1-76-P2 (11.9 g, 33.3 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (12.70 g, 50.0 mmol), Pd2(dba) (31.93 g, 1.67 mmol), Sphos (1.37 g, 3.33 mmol), and KOAc (6.47 g, 66.6 mmol) were dissolved in 120 mL of 1,4-dioxane and refluxed and stirred for 6 hours. After completion of the reaction, the mixture was extracted with distilled water and DCM at room temperature. The organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reaction mixture was purified by column chromatography (DCM:Hex = 1:2) to yield 14.5 g (94.8%) of the desired compound 1-76-P1.

[0249] 4) Preparation of Compound 1-76 The compound 1-76-P1 (14.5 g, 31.4 mmol), 2-([1,1'-biphenyl]-3-yl)-4-([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (13.7 g, 32.7 mmol), Pd(PPh3) (1.89 g, 1.64 mmol), and K2CO3 (9.04 g, 65.4 mmol) were dissolved in 1,4-dioxane / HO (150 mL / 45 mL) and refluxed for 24 hours. After completion of the reaction, the mixture was extracted with distilled water and DCM at room temperature. The organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reaction mixture was purified by column chromatography (DCM:Hex = 1:3) and recrystallized from methanol to yield the target compound 1-76 (20.4 g, 89.4%).

[0250] <Preparation Example 4> Preparation of Compounds 1-121, 1-124, 1-131 and 1-134 The target compound was synthesized in the same manner as in Preparation Example 3, except that Intermediate A in Table 2 below was used instead of 9H-carbazole and Intermediate B was used instead of 2-([1,1'-biphenyl]-3-yl)-4-([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine.

[0251] [Table 2]

[0252] <Production Example 5> Production of Compound 1-135 [ka]

[0253] 1) Preparation of Compound 1-135-P3 10 g (35.4 mmol) of the 1-135-P4 was dissolved in 500 mL of Benzene-d6, then dissolved in 90.3 g (601.8 mmol) of CFSOH and refluxed at 60°C for 1 hour. After completion of the reaction, the mixture was neutralized with D2O and Na2CO3. After neutralization, the mixture was extracted with distilled water and ethyl acetate. The organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex=1:4) and purified with methanol to obtain 9.69 g (93%) of the target compound 1-135-P3.

[0254] 2) Preparation of Compound 1-135-P2 9.69 g (32.9 mmol) of the 1-135-P3 and 5.50 g (32.9 mmol) of 9H-carbazole were dissolved in 97 mL of DMA, followed by the addition of 10.7 g (32.9 mmol) of CsCO and refluxing at 180 °C for 3 hours. After the reaction was complete, a solid was obtained using HO. The solid compound was purified by column chromatography (DCM:Hex = 1:2) and added to methanol to obtain 12.1 g (88.3%) of the target compound 1-135-P2.

[0255] 3) Preparation of Compound 1-135-P1 Compound 1-135-P2 (12.1 g, 27.4 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (10.4 g, 41.1 mmol), Pd2(dba)3 (1.25 g, 1.37 mmol), Sphos (1.12 g, 2.74 mmol), and KOAc (5.32 g, 54.8 mmol) were dissolved in 120 mL of 1,4-dioxane and refluxed and stirred for 6 hours. After completion of the reaction, the mixture was extracted with distilled water and DCM at room temperature. The organic layer was dried over MgSO4 and the solvent was removed by rotary evaporation. The reaction mixture was purified by column chromatography (DCM:Hex = 1:2) to yield 14.0 g (95.9%) of the desired compound 1-135-P1.

[0256] 4) Preparation of Compound 1-135 The compound 1-135-P1 (14.0 g, 26.2 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (7.01 g, 26.2 mmol), Pd(PPh3) (1.5 g, 1.31 mmol), and K2CO3 (7.24 g, 52.4 mmol) were dissolved in 1,4-dioxane / HO (150 mL / 45 mL) and refluxed for 24 hours. After completion of the reaction, the mixture was extracted with distilled water and DCM at room temperature. The organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reaction mixture was purified by column chromatography (DCM:Hex = 1:3) and recrystallized from methanol to yield the target compound 1-135 (14.7 g, 87.7%).

[0257] <Preparation Example 6> Preparation of Compounds 1-136, 1-140 and 1-149 The target compound was synthesized in the same manner as in Preparation Example 5, except that Intermediate A in Table 3 below was used instead of 9H-carbazole and Intermediate B was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0258] [Table 3]

[0259] <Production Example 7> Production of Compound 1-146 [ka]

[0260] 1) Preparation of Compound 1-146-P3 10 g (35.4 mmol) of the 1-146-P4 was dissolved in 500 mL of Benzene-d6, then dissolved in 90.3 g (601.8 mmol) of CFSOH and refluxed at 60°C for 1 hour. After completion of the reaction, the mixture was neutralized with D2O and Na2CO3. After neutralization, the mixture was extracted with distilled water and ethyl acetate. The organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex=1:4) and purified with methanol to obtain 10.1 g (97%) of the target compound 1-146-P3.

[0261] 2) Preparation of Compound 1-146-P2 10.1 g (34.3 mmol) of the 1-146-P3 and 6.01 g (34.3 mmol) of 9H-carbazole-1,2,3,4,5,6,7,8-d8 (9H-carbazole-1,2,3,4,5,6,7,8-d8) were dissolved in 97 mL of DMA, and then 11.2 g (34.3 mmol) of CsCO was added and refluxed at 180 °C for 3 hours. After the reaction was complete, a solid was obtained using HO. The solid compound was purified by column chromatography (DCM:Hex = 1:2) and added to methanol to obtain 13.1 g (85.1%) of the target compound 1-146-P2.

[0262] 3) Preparation of Compound 1-146-P1 Compound 1-146-P2 (13.1 g, 29.1 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (11.1 g, 43.7 mmol), Pd2(dba)3 (1.33 g, 1.45 mmol), Sphos (1.19 g, 2.90 mmol), and KOAc (5.65 g, 58.2 mmol) were dissolved in 130 mL of 1,4-dioxane and refluxed and stirred for 6 hours. After completion of the reaction, the mixture was extracted with distilled water and DCM at room temperature. The organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reaction mixture was purified by column chromatography (DCM:Hex = 1:2) to yield 13.8 g (87.5%) of the desired compound 1-146-P1.

[0263] 4) Preparation of Compound 1-146 The compound 1-146-P1 (13.8 g, 25.5 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (6.83 g, 25.5 mmol), Pd(PPh3) (1.48 g, 1.28 mmol), and K2CO3 (7.05 g, 51.0 mmol) were dissolved in 1,4-dioxane / HO (150 mL / 45 mL) and refluxed for 24 hours. After completion of the reaction, the mixture was extracted with distilled water and DCM at room temperature. The organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reaction mixture was purified by column chromatography (DCM:Hex = 1:3) and recrystallized from methanol to yield the target compound 1-146 (15.1 g, 91.6%).

[0264] <Preparation Example 8> Preparation of Compounds 1-147, 1-148 and 1-151 The target compound was synthesized in the same manner as in Preparation Example 7, except that Intermediate A in Table 4 below was used instead of 9H-carbazole-1,2,3,4,5,6,7,8-d8 and Intermediate B was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0265] [Table 4]

[0266] <Production Example 9> Production of Compound 2-1 [ka]

[0267] 1) Preparation of Compound 2-1-1 A reaction flask was charged with 10 g (49.59 mmol) of 3-bromo-9H-carbazole, 24.2 g (148.77 mmol) of 2-bromobenzene-1-ylium(a), 2.27 g (2.48 mmol) of tris(dibenzylideneacetone) dipalladium (Pd2(dba)3), 2.42 mL (9.92 mmol) of tri-tert-butylphosphine (P(t-Bu)3), and 9.53 g (99.18 mmol) of sodium tert-butoxide (NatOBu), followed by 100 mL of toluene. The mixture was heated at 135 °C for 15 hours. After the reaction was completed, the reaction mixture was extracted with methylene chloride (MC) and water, and then purified by column chromatography to obtain 14 g of compound 2-1-1 (yield 98%).

[0268] 2) Preparation of Compound 2-1 A reaction flask was charged with 14 g (43.4 mmol) of the compound 2-1-1, 14.9 g (52 mmol) of (9-phenyl-9H-carbazol-3-yl)boronic acid (b), 2.5 g (2.17 mmol) of tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4), and 17.9 g (130 mmol) of potassium carbonate (K2CO3). The mixture was then added to 140 mL of 1,4-dioxane and 35 mL of distilled water and stirred at 120°C for 4 hours. Thereafter, the temperature was lowered to room temperature, and the solid formed was washed with distilled water and methanol to obtain 17 g (yield 80%) of compound 2-1.

[0269] <Production Example 10> Production of Compounds 2-2, 2-3, 2-4, 2-5, 2-6, 2-7, 2-11, 2-16, 2-19, 2-20, 2-21, 2-22, 2-23, 2-26, 2-27, 2-28, 2-29, 2-30, 2-32, 2-33, 2-34, 2-38, 2-40, 2-53, 2-54, 2-55, 2-57, 2-58, 2-60, 2-61, 2-62, 2-63, 2-64, 2-67, 2-69, and 2-72 Compounds 2-2, 2-3, 2-4, 2-5, 2-6, 2-7, and 2-11 were prepared in the same manner as in Preparation Example 9, except that in Preparation Example 9, compound a in Table 5 below was used instead of 2-bromobenzene-1-ylium (a) and compound b in Table 5 below was used instead of (9-phenyl-9H-carbozol-3-yl)boronic acid (b). , 2-16, 2-19, 2-20, 2-21, 2-22, 2-23, 2-26, 2-27, 2-28, 2-29, 2-30, 2-32, 2-33, 2-34, 2-38, 2-40, 2-53, 2-54, 2-55, 2-57, 2-58, 2-60, 2-61, 2-62, 2-63, 2-64, 2-67, 2-69 and 2-72 were synthesized.

[0270] [Table 5A]

[0271] [Table 5B]

[0272] [Table 5C]

[0273] Table 5D

[0274]

Table 5E

[0275] Table 5F

[0276]

Table 5G

[0277] Table 5H

[0278] Table 5I

[0279]

Table 5J

[0280] <Production Example 11> Production of Compound 2-73

change

[0281] 1) Preparation of Compound 2-73-4 10 g (40.23 mmol) of 3-bromo-9H-carbazole, 1,000 mL of D6-benzene, and 170 g (1,075 mmol) of triflic acid (CF3SO3H) were added and stirred at 50°C. Upon completion of the reaction, the mixture was neutralized with DO and extracted with aqueous sodium carbonate (NaCO) and dichloromethane (DCM) at room temperature. The organic layer was dried over anhydrous magnesium sulfate (MgSO) and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (dichloromethane:hexane = 1:2) and recrystallized from methanol to obtain 10 g of the target compound 2-73-4 (98% yield).

[0282] 2) Preparation of Compound 2-73-3 10 g (39.5 mmol) of the compound 2-73-4, 12.4 g (79 mmol) of bromobenzene (c), 1.81 g (1.98 mmol) of tris(dibenzylideneacetone)dipalladium (Pd2(dba)3), 1.93 mL (7.9 mmol) of tri-tert-butylphosphine (P(t-Bu)3), and 11.4 g (118.51 mmol) of sodium tert-butoxide (NatOBu) were added, followed by the addition of 100 mL of toluene, and the mixture was heated at 135° C. for 15 hours. After the reaction was completed, the reaction mixture was extracted with methylene chloride (MC) and water, and then purified by column chromatography to obtain 11 g of compound 2-73-3 (yield 84%).

[0283] 3) Preparation of Compound 2-73-2 10 g (47.3 mmol) of 9H-carbazol-3-ylboronic acid, 1,000 mL of D6-benzene, and 170 g (1,075 mmol) of trifluoromethanesulfonic acid (CF3SO3H) were added and stirred at 50°C. Upon completion of the reaction, the mixture was neutralized with DO and extracted with aqueous sodium carbonate (NaCO) and dichloromethane (DCM) at room temperature. The organic layer was dried over anhydrous magnesium sulfate (MgSO) and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (dichloromethane:hexane = 1:2) and recrystallized from methanol to obtain 9 g of the target compound 2-73-2 (87% yield).

[0284] 4) Preparation of Compound 2-73-1 9 g (41.3 mmol) of the compound 2-73-2, 12.9 g (82.5 mmol) of bromobenzene (d), 1.89 g (2.06 mmol) of tris(dibenzylideneacetone)dipalladium (Pd2(dba)3), 2 mL (8.25 mmol) of tri-tert-butylphosphine (P(t-Bu)3), and 7.93 g (82.574 mmol) of sodium tert-butoxide (NatOBu) were added, followed by the addition of 100 mL of toluene, and the mixture was heated at 135° C. for 10 hours. After the reaction was completed, the reaction mixture was extracted with methylene chloride (MC) and water, and then purified by column chromatography to obtain 10 g of compound 2-73-1 (yield 82%).

[0285] 5) Preparation of Compound 2-73 10 g (30.37 mmol) of the compound 2-73-3, 17.87 g (60.75 mmol) of the compound 2-61-1, 1.39 g (1.52 mmol) of tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4), and 12.59 g (91.13 mmol) of potassium carbonate (K2CO3) were added, and then 140 mL of 1,4-dioxane and 35 mL of distilled water were added, followed by stirring at 120°C for 4 hours. Thereafter, the temperature was lowered to room temperature, and the solid formed was washed with distilled water and methanol to obtain 13 g (yield 85%) of compound 2-73.

[0286] <Preparation Example 12> Preparation of Compounds 2-74, 2-75, 2-76, 2-77, 2-78, 2-80, 2-81, 2-82, 2-86, 2-87, 2-94, 2-95, 2-97, 2-98, 2-99, 2-100, 2-101, 2-102, 2-104, 2-112, and 2-114 Compounds 2-74, 2-75, 2-76, 2-77, 2-78, 2-80, 2-81, 2-82, 2-86, 2-87, 2-94, 2-95, 2-97, 2-98, 2-99, 2-100, 2-101, 2-102, 2-104, 2-112, and 2-114 were synthesized in the same manner as in Production Example 11, except that compound c in Table 6 below was used instead of bromobenzene (c) and compound d in Table 6 below was used instead of bromobenzene (d).

[0287] [Table 6A]

[0288] [Table 6B]

[0289] [Table 6C]

[0290] [Table 6D]

[0291] [Table 6E]

[0292] [Table 6F]

[0293] <Production Example 13> Production of Compound 2-93 [ka]

[0294] 10 g (15.7 mmol) of compound 2-93-1 (compound 2-32), 1,000 mL of D6-benzene, and 170 g (1,075 mmol) of trifluoromethanesulfonic acid (CF3SO3H) were added and stirred at 50°C. Upon completion of the reaction, the mixture was neutralized with DO and extracted with aqueous sodium carbonate (NaCO) and dichloromethane (DCM) at room temperature. The organic layer was dried over anhydrous magnesium sulfate (MgSO) and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (dichloromethane:hexane = 1:2) and recrystallized from methanol to give 10.0 g (95% yield) of the target compound 2-93.

[0295] <Production Example 14> Production of Compound 3-1 [ka]

[0296] 1) Preparation of Compound 3-1-1 A reaction flask was charged with 10 g (39.0 mmol) of (a) 5,8-dihydroindolo[2,3-c]carbazole, 6.12 g (39.0 mmol) of 1-bromobenzene, 1.79 g (1.95 mmol) of tris(dibenzylideneacetone)dipalladium (Pd2(dba)3), 0.92 mL (3.9 mmol) of tri-tert-butylphosphine (P(t-Bu)3), and 7.50 g (78.0 mmol) of sodium tert-butoxide (NatOBu), followed by 100 mL of toluene. The mixture was heated at 135 °C for 15 hours. After the reaction was completed, the reaction mixture was extracted with methylene chloride (MC) and water, and then purified by column chromatography to obtain 7.3 g of compound 3-1-1 (yield 56%).

[0297] 2) Preparation of Compound 3-1 7.3 g (22.0 mmol) of the compound 3-1-1, (b) 3.8 g (24.2 mmol) of 1-bromobenzene, 1.01 g (1.1 mmol) of tris(dibenzylideneacetone)dipalladium (Pd2(dba)3), 0.52 mL (3.9 mmol) of tri-tert-butylphosphine (P(t-Bu)3), and 4.23 g (44.0 mmol) of sodium tert-butoxide (NatOBu) were added, and then 70 mL of toluene was added, followed by heating at 135° C. for 15 hours. After the reaction was completed, the reaction mixture was extracted with methylene chloride (MC) and water, and then purified by column chromatography to obtain 8.3 g of compound 3-1 (yield 93%).

[0298] <Preparation Example 15> Preparation of Compounds 3-4, 3-5, 3-22, 3-23, 3-32, 3-35, 3-41, 3-61, 3-69, 3-77, 3-96 and 3-99 The target compound was synthesized in the same manner as in Production Example 14, except that in Production Example 14, Intermediate A in Table 7 below was used instead of (a), Intermediate B in Table 7 below was used instead of (b), and Intermediate C in Table 7 below was used instead of (c).

[0299] [Table 7A]

[0300] [Table 7B]

[0301] [Table 7C]

[0302] Compounds other than those described in Preparation Examples 1 to 15 and Tables 1 to 7 were also prepared in the same manner as described in the above Preparation Examples, and the synthesis results are shown in Tables 8 and 9 below. 1 The values ​​are measured by H NMR (CDCl3, 400 MHz), and Table 9 below shows the values ​​measured by FD-MS (Field desorption mass spectrometry).

[0303] [Table 8A]

[0304] [Table 8B]

[0305] [Table 8C]

[0306] [Table 8D]

[0307] [Table 8E]

[0308] [Table 8F]

[0309] [Table 9A]

[0310] [Table 9B]

[0311] [Table 9C] <Experimental Example 1> 1) Fabrication of organic light-emitting devices A glass substrate coated with a 1,500Å thick ITO film was ultrasonically cleaned with distilled water. After the distilled water cleaning, the substrate was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UVO (Ultraviolet / ozone) for 5 minutes using UV in a UV cleaner. The substrate was then transferred to a plasma cleaner (PT) and plasma treated in a vacuum to remove the ITO work function and residual film, before being transferred to a thermal evaporation device for organic deposition.

[0312] A common layer, a hole injection layer made of 2-TNATA (4,4',4''-Tris[2-naphthyl(phenyl)amino]triphenylamine) and a hole transport layer made of NPB (N,N'-Di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine), were formed on the ITO transparent electrode (positive electrode). [ka]

[0313] An emitting layer was then formed thereon by thermal vacuum deposition as follows. The emitting layer used the compound shown in Table 10 below as the host and Ir(ppy)3 (tris(2-phenylpyridine)iridium) as the green phosphorescent dopant. The host was doped with Ir(ppy)3 at 6% and deposited to a thickness of 350 Å. Next, BCP was deposited to a thickness of 70 Å as a hole-blocking layer, and Alq3 was deposited to a thickness of 250 Å as an electron-transporting layer. Finally, lithium fluoride (LiF) was deposited to a thickness of 10 Å on the electron-transporting layer to form an electron-injecting layer. An aluminum (Al) anode was then deposited to a thickness of 1,200 Å on the electron-injecting layer to form the anode, completing the fabrication of an organic electroluminescent device. [ka]

[0314] In Table 10 below, the examples and comparative examples were used as green hosts. Meanwhile, all organic compounds required for manufacturing OLED devices were used as 100% by material. -8 ~10 -6 It was purified by vacuum sublimation under torr and used for OLED fabrication.

[0315] [Comparative Example Compound] [ka]

[0316] [Table 10A]

[0317] [Table 10B]

[0318] As can be seen from the results in Table 10, Examples 1 to 36, which are organic light-emitting devices using the compound represented by Chemical Formula 1 of the present invention as an emission layer material (especially, a green phosphorescent host), exhibited lower driving voltages and significantly improved luminous efficiency and lifetimes compared to Comparative Examples 1 to 19, which are organic light-emitting devices not using the compound represented by Chemical Formula 1 of the present invention as an emission layer material.

[0319] When a strong electron donor and a strong electron acceptor are directly bonded within a molecule, the HOMO-LUMO overlap can cause a decrease in lifetime, but by introducing a biphenyl linker, the HOMO-LUMO overlap can be offset and lifetime can be increased. In particular, when the linker of the electron acceptor is meta-shaped, it further reduces the resonance effect, unlike ortho- and para-shaped linkers, effectively offsetting the HOMO-LUMO overlap.

[0320] In addition, when the electron donor is ortho-shaped, the HOMO and the linking group face each other in space due to steric hindrance in space, which suppresses through bond charge transfer (TBCT) and has a long lifespan, and causes through space charge transfer (TSCT), which shows thermally activated delayed fluorescence (TADF) properties, effectively demonstrating high efficiency properties through spatial charge transfer between the electron donor and electron acceptor.

[0321] In general, compounds bonded with hydrogen and compounds substituted with deuterium have different thermodynamic behavior. This is because the mass of a deuterium atom is twice as large as that of hydrogen, and due to the difference in atomic mass, deuterium has the characteristic of having lower vibrational energy. In addition, the bond length between carbon and deuterium is shorter than that of a hydrogen bond, and the dissociation energy required to break the bond is also stronger. This is because the van der Waals radius of deuterium is smaller than that of hydrogen, and the stretching amplitude of the carbon-deuterium bond is narrower.

[0322] The deuterium-substituted compounds of the present invention have higher luminescence efficiency than unsubstituted compounds due to the weaker intermolecular van der Waals forces generated by the shorter carbon-deuterium bond length compared to the carbon-hydrogen bond length. Furthermore, the zero-point energy (i.e., ground state energy) is lowered and the shorter carbon-deuterium bond length reduces the molecular hard-core volume, thereby reducing electronic polarizability and increasing the thin film volume by weakening intermolecular interactions. These characteristics induce an amorphous state in the thin film, reducing the crystallinity. Consequently, deuterium substitution effectively improves the heat resistance of organic light-emitting devices, thereby improving their lifetime and operating characteristics. Furthermore, the improvement in device characteristics due to deuterium substitution increases with increasing the deuterium substitution rate in the molecule.

[0323] For materials used in organic light-emitting devices, the stability of the ground state and excited state is an important factor in determining device lifetime. In the case of a linking group, this is the position where the HOMO and LUMO intersect. When a molecule enters an excited state, this position can cause significant structural changes in the molecular structure, which can significantly affect device lifetime. The compound of the present invention was developed by substituting deuterium, which has a larger molecular weight, for the linking group, thereby reducing changes in vibrational frequency and lowering molecular energy, thereby improving molecular stability. Furthermore, because the single bond dissociation energy between carbon and deuterium is higher than the single bond dissociation energy between carbon and hydrogen, it can be confirmed that the increased thermal stability of the molecule leads to improved device lifetime.

[0324] When deuterium is substituted, the charge mobility increases due to the short intermolecular distance, which can be confirmed to improve the device life. As in Examples 20 to 22, it can be confirmed that the device characteristics improve as the deuterium substitution rate in the molecule increases.

[0325] In Comparative Examples 1 to 3, 5, 6, 8, 10, and 13 to 19, which were not substituted with deuterium, the electron mobility in the molecule was faster than the hole mobility, which resulted in the recombination zone being biased toward the hole transfer layer (HTL), resulting in reduced efficiency and lifetime of the device.

[0326] On the other hand, in Comparative Example 9, the phenyl group corresponding to the HOMO was substituted with deuterium, but since the carbazole and the linking group did not contain deuterium, the contribution of deuterium to the stability of the ground state and the excited state was small, making it difficult to confirm the effect. This suggests that the properties of compounds with similar structures may change depending on the deuterium substitution.

[0327] On the other hand, in Comparative Examples 4, 6, 7, and 11, the addition of strong electron donor substituents in the molecule resulted in strong HT characteristics, which made it impossible to effectively stabilize electrons, thereby shortening the lifetime.

[0328] On the other hand, it was confirmed that the strong HOMO-LUMO overlap could not be effectively offset in Comparative Examples 1, 2, 12, 13, and 14, resulting in poor lifetime when used in devices. Also, in Comparative Example 2, the electron acceptor contained an ortho-type, and in this case, it was confirmed that the device exhibited very poor lifetime characteristics due to excessive steric hindrance.

[0329] On the other hand, in Comparative Examples 18 and 19, the linking group was in the form of para-terphenyl, and it was found that the efficiency when applied to devices was poor. In general, para-terphenyls are characterized by high thermal stability due to their strong resonance effect, which increases molecular stability. However, since a strong resonance structure also has the characteristic of lowering the triplet excited state (T1 state), a host with such a low triplet excited state causes energy back transfer of the dopant, which in turn competes with the dopant's emission. As a result, it was found that when materials with linking groups with such strong resonance structures are applied to devices, the efficiency is poor.

[0330] <Experimental Example 2> 1) Fabrication of organic light-emitting devices A glass substrate coated with a 1,500Å thick ITO film was ultrasonically cleaned with distilled water. After the distilled water cleaning, the substrate was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UVO (Ultraviolet / ozone) for 5 minutes using UV in a UV cleaner. The substrate was then transferred to a plasma cleaner (PT) and plasma treated in a vacuum to remove the ITO work function and residual film, before being transferred to a thermal evaporation device for organic deposition.

[0331] A common layer, a hole injection layer made of 2-TNATA (4,4',4''-Tris[2-naphthyl(phenyl)amino]triphenylamine) and a hole transport layer made of NPB (N,N'-Di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine), were formed on the ITO transparent electrode (positive electrode). [ka]

[0332] An emitting layer was then formed thereon by thermal vacuum deposition as follows: The emitting layer was formed by premixing two compounds (N-host and P-host) listed in Table 11 below as hosts in the weight ratios listed in Table 11 below and depositing them to a thickness of 350 Å using a single light source. The green phosphorescent dopant, Ir(ppy)3, was doped to a thickness of 6% of the emitting layer deposition thickness. Next, BCP was deposited to a thickness of 70 Å as a hole-blocking layer, and Alq3 was deposited to a thickness of 250 Å as an electron-transporting layer on top of that. Finally, lithium fluoride (LiF) was deposited to a thickness of 10 Å on the electron-transporting layer to form an electron-injecting layer. An aluminum (Al) anode was then deposited to a thickness of 1,200 Å on the electron-injecting layer to form a cathode, completing the fabrication of an organic electroluminescent device. [ka]

[0333] Meanwhile, all the organic compounds required for manufacturing OLED devices are 10 -8 ~10 -6 It was purified by vacuum sublimation under torr and used for the fabrication of OLEDs.

[0334] The electroluminescence (EL) characteristics of the organic electroluminescent device fabricated as described above were measured using a Mac Science M7000. Based on the measurement results, a reference luminance of 12,000 cd / m was measured using a Mac Science M6000 lifespan measurement device. 2 At the time, T 90 was measured.

[0335] The driving voltage, luminous efficiency, color, and lifespan of the organic light emitting device manufactured according to the present invention were measured, and the results are shown in Table 11 below.

[0336] [Table 11A]

[0337] [Table 11B]

[0338] [Table 11C]

[0339] [Table 11D]

[0340] [Table 11E]

[0341] The comparative compounds used in Table 11 are the same as those in Table 10. Comparing the results of Table 11 with those of Table 10, it can be seen that when the heterocyclic compound represented by Chemical Formula 1 of the present invention and the heterocyclic compound represented by Chemical Formula 2 or 3 are used simultaneously as hosts in the emission layer, specifically, when the heterocyclic compound represented by Chemical Formula 1 is used as an N-type host and the heterocyclic compound represented by Chemical Formula 2 or 3 is used as a P-type host, the driving voltage, luminous efficiency, and lifetime are all improved.

[0342] From these results, it can be predicted that an exciplex phenomenon occurs when two compounds are present at the same time. The exciplex phenomenon is a phenomenon in which electron exchange between two molecules releases energy at the HOMO level of the donor (p-host) and the LUMO level of the acceptor (n-host). The exciplex phenomenon between the two molecules leads to reverse intersystem crossing (RISC), which can potentially increase the internal quantum efficiency of fluorescence to 100%. When a donor (p-host) with good hole transporting ability and an acceptor (n-host) with good electron transporting ability are used as hosts in the emissive layer, holes are injected into the p-host and electrons are injected into the n-host, thereby reducing the driving voltage and improving the lifetime. In the present invention, it was found that the heterocyclic compound represented by Formula 1 acts as an acceptor, and the heterocyclic compounds represented by Formulas 2 and 3 act as donors, thereby demonstrating excellent device characteristics when used together as hosts in the emissive layer.

[0343] On the other hand, when the comparative compounds are used in combination with the compounds of Chemical Formula 2 or 3 (Comparative Examples 20 to 76), the performance in terms of driving voltage, luminous efficiency, and lifetime is found to be reduced compared to when the heterocyclic compound represented by Chemical Formula 1 according to the present invention is used.

[0344] That is, when the heterocyclic compound represented by Chemical Formula 1 of the present invention and the heterocyclic compound represented by Chemical Formula 2 or 3 are simultaneously used as hosts in the light-emitting layer, it is confirmed that the driving voltage, luminous efficiency, and lifespan are very excellent. [Explanation of symbols]

[0345] 100: Substrate 200: Positive electrode 300:Organic layer 301: Hole injection layer 302: Hole transport layer 303: Light-emitting layer 304: Hole blocking layer 305: Electron transport layer 306: Electron injection layer 400: Negative electrode

Claims

1. A heterocyclic compound represented by the following chemical formula 1: 【Chemistry 1】 In the above Chemical Formula 1, Y1 to Y3 are the same or different and each independently represents CH; or N; At least one of Y1 to Y3 is N, Ar1 and Ar2 are the same or different and each independently represent a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group; L1 and L2 are the same or different and each independently represent a single bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group; R1 are the same or different and each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C3-C60 cycloalkyl group, a substituted or unsubstituted C2-C60 heterocycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, or a substituted or unsubstituted C2-C60 heteroaryl group; R2 to R9 are the same or different and each independently represent hydrogen; deuterium; a C1 to C60 alkyl group substituted or unsubstituted with deuterium; a C3 to C60 cycloalkyl group substituted or unsubstituted with deuterium; a C2 to C60 heterocycloalkyl group substituted or unsubstituted with deuterium; a C6 to C60 aryl group substituted or unsubstituted with deuterium; or a C2 to C60 heteroaryl group substituted or unsubstituted with deuterium; At least one of R2 to R9 is a deuterium or a C6 to C60 aryl group substituted with deuterium, n1 is an integer from 0 to 8, n2 and n3 are the same or different and each independently represents an integer of 0 to 4, When n1, n2 and n3 are 2 or more, R1, L1 and L2 are the same or different.

2. The heterocyclic compound according to claim 1, wherein Ar1 and Ar2 are represented by any one of the following chemical formulas 1-1 to 1-3: 【Chemistry 2】 In the above Chemical Formula 1-1 to Chemical Formula 1-3, X is O or S; Ar3 is a substituted or unsubstituted C6-C60 aryl group; R10 to R13 are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1 to C60 alkyl, substituted or unsubstituted C2 to C60 alkenyl, substituted or unsubstituted C2 to C60 alkynyl, substituted or unsubstituted C1 to C60 alkoxy, substituted or unsubstituted C3 to C60 cycloalkyl, substituted or unsubstituted C2 to C60 heterocycloalkyl, substituted or unsubstituted C6 to C60 aryl, and substituted or unsubstituted C2 to C60 heteroaryl, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring, or a substituted or unsubstituted C2 to C60 heterocycle; * is a moiety that is linked to Chemical Formula 1, n4, n6, and n7 are the same or different and each independently represents an integer of 0 to 4; n5 is an integer from 0 to 3, When n4 to n7 are 2 or more, R10 to R13 are the same or different.

3. When Ar1 or Ar2 in the above Chemical Formula 1 is represented by Chemical Formula 1-2, The heterocyclic compound according to claim 2, wherein L1 and L2 in Chemical Formula 1 are the same or different and each independently represent a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group.

4. The heterocyclic compound according to claim 1, wherein R1 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

5. 2. The heterocyclic compound according to claim 1, wherein the heterocyclic compound represented by Chemical Formula 1 has a deuterium content of 1% to 100% based on the total number of hydrogen atoms and deuterium atoms.

6. The heterocyclic compound represented by Chemical Formula 1 is the heterocyclic compound according to claim 1, which is represented by any one of the following compounds: 【Chemistry 3A】 【Chemistry 3B】 【Chemicals 3C】 [3D Transformation] 【3E Transformation】 【Chemical 3F】 [3G Transformation] 【Chemical 3H】 。

7. First electrode; a second electrode disposed opposite the first electrode; and one or more organic layers provided between the first electrode and the second electrode; As an organic light-emitting element comprising:

10. An organic light-emitting device, wherein at least one of the organic layers comprises the heterocyclic compound according to claim 1.

8. the organic layer includes a light-emitting layer, 8. The organic light-emitting device according to claim 7, wherein the light-emitting layer comprises the heterocyclic compound represented by Chemical Formula 1.

9. the organic layer includes a light-emitting layer, the light-emitting layer comprises a host material; 8. The organic light-emitting device according to claim 7, wherein the host material comprises a heterocyclic compound represented by Chemical Formula 1.

10. The organic light-emitting device according to claim 7, wherein the organic material layer further contains a heterocyclic compound represented by the following Chemical Formula 2 or Chemical Formula 3: 【Chemistry 4】 【Transformation 5】 In the above Chemical Formula 2 and Chemical Formula 3, L3 to L7 are the same or different and each independently represent a single bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group; Ar4 to Ar7 are the same or different and each independently represent a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; R15 to R19 are the same or different and each independently represent hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C2 to C60 alkenyl group; substituted or unsubstituted C2 to C60 alkynyl group; substituted or unsubstituted C1 to C60 alkoxy group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or unsubstituted C2 to C60 heterocycloalkyl group; substituted or unsubstituted C6 to C60 aryl group; or substituted or unsubstituted C2 to C60 heteroaryl. or -SiR101R102R103; or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same or different and each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; m1 to m5 are the same or different and each independently represents an integer of 0 to 3; e and f are the same or different and each independently represents an integer of 0 to 7; g and h are the same or different and each independently represents an integer of 0 to 4; i is an integer from 0 to 2, When m1 to m5, e, f, g, h, and i are 2 or more, L3 to L7 and R15 to R19 are the same as or different from each other.

11. The organic light-emitting device according to claim 10, wherein Ar4 to Ar7 are represented by any one of the following Chemical Formula 2-1 or Chemical Formula 2-2: 【Transformation 6】 【Transformation 7】 In the above Chemical Formula 2-1 and Chemical Formula 2-2, X3 is O; S; or CRaRb; Ar8 is a substituted or unsubstituted C6-C60 aryl group; R20, R21, Ra, and Rb are the same or different and each independently represent hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C2 to C60 alkenyl group; substituted or unsubstituted C2 to C60 alkynyl group; substituted or unsubstituted C1 to C60 alkoxy group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or unsubstituted C2 to C60 heterocycloalkyl group; substituted or unsubstituted C6 to C60 aryl group; substituted or unsubstituted C2 to C60 heteroaryl group. or -SiR101R102R103; or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same or different and each independently represent a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; * is a moiety linked to Chemical Formula 2 or Chemical Formula 3, j is an integer from 0 to 4, k is an integer from 0 to 3, When j and k are 2 or more, R20 and R21 are the same or different.

12. 11. The organic light-emitting device according to claim 10, wherein the heterocyclic compound represented by Chemical Formula 2 or Chemical Formula 3 does not contain deuterium as a substituent, or the deuterium content is 1% to 100% based on the total number of hydrogen atoms and deuterium atoms.

13. The organic light-emitting device according to claim 10, wherein the heterocyclic compound represented by Chemical Formula 2 is represented by any one of the following compounds: 【Chemical Engineering 8A】 【Chemical 8B】 【Chemical 8C】 【8D】 【Chemical 8E】 【Chemical 8F】 。

14. The organic light-emitting device according to claim 10, wherein the heterocyclic compound represented by Chemical Formula 3 is represented by any one of the following compounds: 【Chemical Engineering 9A】 【Chemical 9B】 【Chemical 9C】 【9D】 【Chem.9E】 【Chemical 9F】 【9G】 。

15. 8. The organic light-emitting device according to claim 7, further comprising one or more layers selected from the group consisting of an emitting layer, a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron injection layer, an electron transport layer, a cell blocking layer, and a hole blocking layer.

16. A composition for an organic layer, comprising the heterocyclic compound according to any one of claims 1 to 6 and a heterocyclic compound represented by the following chemical formula 2 or 3: 【Chemistry 10】 【Chemistry 11】 [chemical 2] In the above Chemical Formula 2 and Chemical Formula 3, L3 to L7 are the same or different and each independently represent a single bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group; Ar4 to Ar7 are the same or different and each independently represent a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; R15 to R19 are the same or different and each independently represent hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C2 to C60 alkenyl group; substituted or unsubstituted C2 to C60 alkynyl group; substituted or unsubstituted C1 to C60 alkoxy group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or unsubstituted C2 to C60 heterocycloalkyl group; substituted or unsubstituted C6 to C60 aryl group; substituted or unsubstituted C2 to C60 heteroaryl group. or two or more adjacent groups bond together to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same or different and each independently represent a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; m1 to m5 are the same or different and each independently represents an integer of 0 to 3; e and f are the same or different and each independently represents an integer of 0 to 7; g and h are the same or different and each independently represents an integer of 0 to 4; i is an integer from 0 to 2, When m1 to m5, e, f, g, h, and i are 2 or more, L3 to L7 and R15 to R19 are the same as or different from each other.

17. 17. The composition for organic layer according to claim 16, wherein a weight ratio of the heterocyclic compound represented by Chemical Formula 1 to the heterocyclic compound represented by Chemical Formula 2 or Chemical Formula 3 in the composition is 1:10 to 10:1.

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