Heterocyclic compound and organic light-emitting device comprising same

Abstract

The present specification pertains to: a heterocyclic compound represented by chemical formula 1; and an organic light-emitting device comprising same. The definitions of the substituents in chemical formula 1 are as set forth in the description.

Description

Heterocyclic compound and organic light-emitting device containing the same

[0001] This application claims the benefit of priority from Republic of Korea Patent Application No. 10-2023-0163315, dated November 22, 2023, and all contents of that Republic of Korea patent application are incorporated herein by reference.

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

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

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

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

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

[0007] [Prior Art Literature]

[0008] [Patent Document]

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

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

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

[0012] [Chemical Formula 1]

[0013]

[0014] In the above chemical formula 1,

[0015] X is O or S,

[0016] Y1 to Y4 are the same or different from each other, and are each independently CRa or N,

[0017] Ra is hydrogen; deuterium; or a group represented by the following chemical formula A,

[0018] L1 is a single bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group,

[0019] Ar1 is a group represented by the following chemical formula 2 or chemical formula 3,

[0020] m1 and n1 are equal to or different from each other and are each independently an integer from 0 to 4,

[0021] If m1 is 2 or more, L1 is equal or different,

[0022] If n1 is 2 or greater, Ar1 is equal or different,

[0023] [Chemical Formula A]

[0024]

[0025] In the above chemical formula A,

[0026] L2 is a single bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group,

[0027] Ar2 is a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group,

[0028] m2 and n2 are equal to or different from each other and are each independently an integer from 0 to 4,

[0029] If m2 is 2 or greater, L2 is equal or different,

[0030] If n2 is 2 or greater, Ar2 is equal or different,

[0031] [Chemical Formula 2]

[0032]

[0033] [Chemical Formula 3]

[0034]

[0035] In the above chemical formulas 2 and 3,

[0036] R1 to R3 are the same as or different from each other, and each independently hydrogen; deuterium; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R101R102; And -SiR101R102R103, or two or more adjacent groups are combined to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same or different from each other and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0037] L3 is a single bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group,

[0038] m3 is an integer from 0 to 4,

[0039] n3 is an integer from 0 to 4,

[0040] If m3 is 2 or greater, L3 is equal or different,

[0041] If n3 is 2 or greater, Ar3 is equal or different.

[0042] In addition, in one embodiment of the present application, an organic light-emitting device is provided, including a first electrode; a second electrode provided opposite the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein the organic layers include one or more types of the heterocyclic compounds.

[0043] The compounds described herein can be used as organic layer materials for organic light-emitting devices. The compounds can serve as hole injection materials, hole transport materials, luminescent materials, electron transport materials, electron injection materials, etc. in organic light-emitting devices. In particular, the compounds can be used as electron transport layer materials or charge generation layer materials in organic light-emitting devices.

[0044] Specifically, when the compound represented by the above chemical formula 1 is used in the organic layer, the driving voltage of the device can be lowered, the light efficiency can be improved, and the lifespan characteristics of the device can be improved due to the thermal stability of the compound.

[0045] Figures 1 to 4 are drawings schematically showing the laminated structure of an organic light-emitting device according to one embodiment of the present application.

[0046] Hereinafter, the present invention will be described in more detail.

[0047] In this specification, the term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position of substitution is not limited as long as it is a position where a hydrogen atom is replaced, i.e., a position where a substituent can be replaced, and when two or more are replaced, the two or more substituents may be the same or different from each other.

[0048] In this specification, "substituted or unsubstituted" means: deuterium; cyano group; straight or branched chain alkyl group having 1 to 60 carbon atoms; straight or branched chain alkenyl group having 2 to 60 carbon atoms; straight or branched chain alkynyl group having 2 to 60 carbon atoms; monocyclic or polycyclic cycloalkyl group having 3 to 60 carbon atoms; monocyclic or polycyclic heterocycloalkyl group having 2 to 60 carbon atoms; monocyclic or polycyclic aryl group having 6 to 60 carbon atoms; monocyclic or polycyclic heteroaryl group having 2 to 60 carbon atoms; -SiRR'R"; -P(=O)RR'; C1 to C20 alkylamine group; C6 to C60 monocyclic or polycyclic arylamine group; and C2 to C60 monocyclic or polycyclic heteroarylamine group, which is substituted or unsubstituted with one or more substituents selected from the group consisting of a C1 to C20 alkylamine group; a C6 to C60 monocyclic or polycyclic arylamine group; and a C2 to C60 monocyclic or polycyclic heteroarylamine group, or substituted or unsubstituted with a substituent in which two or more substituents selected from the above-mentioned substituents are connected.

[0049] In this specification, “proton number” means the number of substituents that a specific compound can have, and specifically, the proton number can mean the number of hydrogens.

[0050] For example, unsubstituted benzene can be represented by the number of protons being 5, unsubstituted naphthyl groups can be represented by the number of protons being 7, naphthyl groups substituted with phenyl groups can be represented by the number of protons being 6, and unsubstituted biphenyl groups can be represented by the number of protons being 9.

[0051] In the present specification, an alkyl group includes a straight or branched chain having 1 to 60 carbon atoms, and may be further substituted by another substituent. The alkyl group may have 1 to 60 carbon atoms, specifically 1 to 40 carbon atoms, and more specifically 1 to 20 carbon atoms. Specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1-ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl-2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, Examples thereof include, but are not limited to, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group, isohexyl group, 4-methylhexyl group, and 5-methylhexyl group.

[0052] In the present specification, the alkenyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted by another substituent. The alkenyl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 2 to 20 carbon atoms. Specific examples include, but are not limited to, a vinyl group, a 1-propenyl group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 3-methyl-1-butenyl group, a 1,3-butadienyl group, an allyl group, a 1-phenylvinyl-1-yl group, a 2-phenylvinyl-1-yl group, a 2,2-diphenylvinyl-1-yl group, a 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl group, a 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, a stilbenyl group, and a styrenyl group.

[0053] In the present specification, an alkynyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted by another substituent. The alkynyl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 2 to 20 carbon atoms.

[0054] In the present specification, the alkoxy group may be linear, branched or cyclic. The carbon number of the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms. Specifically, examples thereof include, but are not limited to, a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, an isobutoxy group, a tert-butoxy group, a sec-butoxy group, an n-pentyloxy group, a neopentyloxy group, an isopentyloxy group, an n-hexyloxy group, a 3,3-dimethylbutyloxy group, a 2-ethylbutyloxy group, an n-octyloxy group, an n-nonyloxy group, an n-decyloxy group, a benzyloxy group, and a p-methylbenzyloxy group.

[0055] In the present specification, a cycloalkyl group includes a monocyclic or polycyclic group having 3 to 60 carbon atoms, and may be further substituted by another substituent. Here, polycyclic means a group in which a cycloalkyl group is directly connected to or condensed with another ring group. Here, the other ring group may be a cycloalkyl group, but may also be another type of ring group, such as a heterocycloalkyl group, an aryl group, a heteroaryl group, etc. The cycloalkyl group may have 3 to 60 carbon atoms, specifically 3 to 40 carbon atoms, and more specifically 5 to 20 carbon atoms. Specifically, there are, but are not limited to, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 3-methylcyclopentyl group, a 2,3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 2,3-dimethylcyclohexyl group, a 3,4,5-trimethylcyclohexyl group, a 4-tert-butylcyclohexyl group, a cycloheptyl group, a cyclooctyl group, etc.

[0056] In the present specification, a heterocycloalkyl group includes O, S, Se, N or Si as a heteroatom, and includes a monocyclic or polycyclic group having 2 to 60 carbon atoms, and may be further substituted by another substituent. Here, polycyclic means a group in which a heterocycloalkyl group is directly connected to or condensed with another ring group. Here, the other ring group may be a heterocycloalkyl group, but may also be another type of ring group, such as a cycloalkyl group, an aryl group, a heteroaryl group, etc. The heterocycloalkyl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 3 to 20 carbon atoms.

[0057] In the present specification, an aryl group includes a monocyclic or polycyclic ring having 6 to 60 carbon atoms, and may be further substituted by another substituent. Here, polycyclic means a group in which an aryl group is directly connected to or condensed with another ring group. Here, the other ring group may be an aryl group, but may also be another type of ring group, such as a cycloalkyl group, a heterocycloalkyl group, a heteroaryl group, etc. The aryl group may include a spiro group. The aryl group may have 6 to 60 carbon atoms, specifically 6 to 40 carbon atoms, and more specifically 6 to 25 carbon atoms. Specific examples of the above aryl group include, but are not limited to, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a chrysenyl group, a phenanthrenyl group, a perylenyl group, a fluoranthenyl group, a triphenylenyl group, a phenalenyl group, a pyrenyl group, a tetracenyl group, a pentacenyl group, a fluorenyl group, an indenyl group, an acenaphthylenyl group, a benzofluorenyl group, a spirobifluorenyl group, a 2,3-dihydro-1H-indenyl group, and condensed ring groups thereof.

[0058] In the present specification, a heteroaryl group includes S, O, Se, N or Si as a heteroatom, and includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted by another substituent. Here, the polycyclic ring means a group in which a heteroaryl group is directly connected to or condensed with another ring group. Here, the other ring group may be a heteroaryl group, but may also be another type of ring group, such as a cycloalkyl group, a heterocycloalkyl group, an aryl group, etc. The heteroaryl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 3 to 25 carbon atoms.Specific examples of the above heteroaryl group include a pyridyl group, a pyrrolyl group, a pyrimidyl group, a pyridazinyl group, a furanyl group, a thiophenyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, a furazanyl group, an oxadiazolyl group, a thiadiazolyl group, a dithiazolyl group, a tetrazolyl group, a pyranyl group, a thiopyranyl group, a diazinyl group, an oxazinyl group, a thiazinyl group, a deoxynyl group, a triazinyl group, a tetrazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, an isoquinazolinyl group, a quinozolinyl group, a naphthyridyl group, an acridinyl group, a phenanthridinyl group, an imidazopyridinyl group, a diazanaphthalenyl group, Triazaindenyl group, 2-indolyl group, indolizinyl group, benzothiazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiophenyl group, benzofuranyl group, dibenzothiophenyl group, dibenzofuranyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, phenazinyl group, dibenzosilole group, spirobi(dibenzosilole) group, dihydrophenazinyl group, phenoxazinyl group, phenanthridyl group, thienyl group, indolo[2,3-a]carbazolyl group, indolo[2,3-b]carbazolyl group, indolinyl group, 10,11-dihydro-dibenzo[b,f]azepinyl group, 9,10-dihydroacridinyl group, phenanthrazinyl group, phenothiazinyl group, Examples thereof include, but are not limited to, a phthalazinyl group, a naphthyridinyl group, a phenanthrolinyl group, a benzo[c][1,2,5]thiadiazolyl group, a 5,10-dihydrodibenzo[b,e][1,4]azacylinyl group, a pyrazolo[1,5-c]quinazolinyl group, a pyrido[1,2-b]indazolyl group, a pyrido[1,2-a]imidazo[1,2-e]indolinyl group, and a 5,11-dihydroindeno[1,2-b]carbazolyl group.

[0059] In the present specification, the phosphine oxide group is represented by -P(=O)R101R102, where R101 and R102 are the same or different, and each independently may be a substituent composed of at least one of hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; an aryl group; and a heterocyclic group. Specifically, it may be substituted with an aryl group, and the above-described examples may be applied to the aryl group. For example, the phosphine oxide group includes, but is not limited to, a diphenylphosphine oxide group, dinaphthylphosphine oxide, etc.

[0060] In the present specification, a silyl group is a substituent that contains Si and is directly connected to the Si atom as a radical, and is represented by -SiR101R102R103, wherein R101 to R103 are the same as or different from each other, and may each independently be a substituent composed of at least one of hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; an aryl group; and a heterocyclic group. Specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.

[0061] In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be combined with each other to form a ring.

[0062] When the above fluorenyl group is substituted, the structural formula below may be used, but is not limited thereto.

[0063]

[0064] In the present specification, a spiro group is a group including a spiro structure and may have 15 to 60 carbon atoms. For example, the spiro group may include a structure in which a 2,3-dihydro-1H-indene group or a cyclohexane group is spiro-bonded to a fluorenyl group. Specifically, the spiro group may include any one of the groups having the following structural formula.

[0065]

[0066] In the present specification, the amine group may be selected from the group consisting of a monoalkylamine group; a monoarylamine group; a monoheteroarylamine group; -NH2; a dialkylamine group; a diarylamine group; a diheteroarylamine group; an alkylarylamine group; an alkylheteroarylamine group; and an arylheteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the above amine group include, but are not limited to, a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, a dibiphenylamine group, anthracenylamine group, a 9-methyl-anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a triphenylamine group, a biphenylnaphthylamine group, a phenylbiphenylamine group, a biphenylfluorenylamine group, a phenyltriphenylenylamine group, and a biphenyltriphenylenylamine group.

[0067] In this specification, an arylene group means a group having two bonding positions to an aryl group, i.e., a divalent group. The description of the aryl group described above may be applied to these groups, except that each group is divalent. In addition, a heteroarylene group means a group having two bonding positions to a heteroaryl group, i.e., a divalent group. The description of the heteroaryl group described above may be applied to these groups, except that each group is divalent.

[0068] As used herein, the term "adjacent" may refer to a substituent substituted on an atom directly connected to the atom substituted by the substituent, a substituent sterically closest to the substituent, or another substituent substituted on the atom substituted by the substituent. For example, two substituents substituted at ortho positions on a benzene ring and two substituents substituted on the same carbon in an aliphatic ring may be interpreted as "adjacent" to each other.

[0069] In the present invention, "when no substituent is indicated in the chemical formula or compound structure" means that a hydrogen atom is bonded to a carbon atom. However, deuterium ( 2 H, Deuterium) is an isotope of hydrogen, so some hydrogen atoms may be deuterium.

[0070] In one embodiment of the present invention, “when no substituent is indicated in the chemical formula or compound structure” may mean that all positions that can be substituted are hydrogen or deuterium. That is, in the case of deuterium, it is an isotope of hydrogen, and some hydrogen atoms may be the isotope deuterium, and in this case, the deuterium content may be 0% to 100%.

[0071] In one embodiment of the present invention, in cases where “no substituent is indicated in the chemical formula or compound structure,” hydrogen and deuterium may be used in combination in the compound, unless deuterium is explicitly excluded, such as “the content of deuterium is 0%,” “the content of hydrogen is 100%,” or “all substituents are hydrogen.”

[0072] In one embodiment of the present invention, deuterium is an element having a deuteron, which is one of the isotopes of hydrogen and is composed of one proton and one neutron, as its nucleus, and can be expressed as hydrogen-2, and its element symbol is D or 2 It can also be written as H.

[0073] In one embodiment of the present invention, an isotope means an atom having the same atomic number (Z) but a different mass number (A), and an isotope can also be interpreted as an element having the same number of protons but a different number of neutrons.

[0074] In one embodiment of the present invention, the content T% of a specific substituent can be defined as T2 / T1×100 = T% when the total number of substituents that the basic compound can have is defined as T1, and the number of specific substituents among them is defined as T2.

[0075] That is, in one example, In the phenyl group represented by , the content of deuterium of 20% can mean that the total number of substituents that the phenyl group can have is 5 (T1 in the formula), and among them, the number of deuterium is 1 (T2 in the formula). That is, the content of deuterium of 20% in the phenyl group can be expressed by the structural formula below.

[0076]

[0077] Additionally, in one embodiment of the present invention, “a phenyl group having a deuterium content of 0%” may mean a phenyl group that does not contain a deuterium atom, i.e., has 5 hydrogen atoms.

[0078] In the present invention, the C6 to C60 aromatic hydrocarbon ring means a compound including an aromatic ring composed of C6 to C60 carbons and hydrogen, and examples thereof include, but are not limited to, benzene, biphenyl, terphenyl, triphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, azulene, etc., and includes all aromatic hydrocarbon ring compounds known in the art that satisfy the above carbon number.

[0079] In one embodiment of the present application, a heterocyclic compound represented by the following chemical formula 1 is provided.

[0080] [Chemical Formula 1]

[0081]

[0082] In the above chemical formula 1,

[0083] X is O or S,

[0084] Y1 to Y4 are the same or different from each other, and are each independently CRa or N,

[0085] Ra is hydrogen; deuterium; or a group represented by the following chemical formula A,

[0086] L1 is a single bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group,

[0087] Ar1 is a group represented by the following chemical formula 2 or chemical formula 3,

[0088] m1 and n1 are equal to or different from each other and are each independently an integer from 0 to 4,

[0089] If m1 is 2 or more, L1 is equal or different,

[0090] If n1 is 2 or greater, Ar1 is equal or different,

[0091] [Chemical Formula A]

[0092]

[0093] In the above chemical formula A,

[0094] L2 is a single bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group,

[0095] Ar2 is a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group,

[0096] m2 and n2 are equal to or different from each other and are each independently an integer from 0 to 4,

[0097] If m2 is 2 or greater, L2 is equal or different,

[0098] If n2 is 2 or greater, Ar2 is equal or different,

[0099] [Chemical Formula 2]

[0100]

[0101] [Chemical Formula 3]

[0102]

[0103] In the above chemical formulas 2 and 3,

[0104] R1 to R3 are the same as or different from each other, and each independently hydrogen; deuterium; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R101R102; And -SiR101R102R103, or two or more adjacent groups are combined to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same or different from each other and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0105] L3 is a single bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group,

[0106] m3 is an integer from 0 to 4,

[0107] n3 is an integer from 0 to 4,

[0108] If m3 is 2 or greater, L3 is equal or different,

[0109] If n3 is 2 or greater, Ar3 is equal or different.

[0110] In one embodiment of the present application, X in chemical formula 1 may be O.

[0111] In one embodiment of the present application, X in chemical formula 1 may be S.

[0112] In one embodiment of the present application, Y1 of chemical formula 1 may be CRa or N.

[0113] In one embodiment of the present application, Y2 of chemical formula 1 may be CRa or N.

[0114] In one embodiment of the present application, Y3 of chemical formula 1 may be CRa or N.

[0115] In one embodiment of the present application, Y4 of chemical formula 1 may be CRa or N.

[0116] In one embodiment of the present application, Y1 of chemical formula 1 may be CRa.

[0117] In one embodiment of the present application, Y1 of chemical formula 1 may be N.

[0118] In one embodiment of the present application, Y2 of chemical formula 1 may be CRa.

[0119] In one embodiment of the present application, Y2 in chemical formula 1 may be N.

[0120] In one embodiment of the present application, Y3 of chemical formula 1 may be CRa.

[0121] In one embodiment of the present application, Y3 of chemical formula 1 may be N.

[0122] In one embodiment of the present application, Y4 of chemical formula 1 may be CRa.

[0123] In one embodiment of the present application, Y4 in chemical formula 1 may be N.

[0124] In one embodiment of the present application, L1 of chemical formula 1 may be a single bond; a substituted or unsubstituted C6 to C40 arylene group; or a substituted or unsubstituted C2 to C40 heteroarylene group.

[0125] In one embodiment of the present application, L1 of chemical formula 1 may be a single bond; a substituted or unsubstituted C6 to C30 arylene group; or a substituted or unsubstituted C2 to C30 heteroarylene group.

[0126] In one embodiment of the present application, L1 of chemical formula 1 may be a single bond; a substituted or unsubstituted C6 to C20 arylene group; or a substituted or unsubstituted C2 to C20 heteroarylene group.

[0127] In one embodiment of the present application, L1 of chemical formula 1 may be a single bond; a substituted or unsubstituted C6 to C10 arylene group; or a substituted or unsubstituted C2 to C10 heteroarylene group.

[0128] In one embodiment of the present application, L1 of chemical formula 1 may 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 naphthylene group; a substituted or unsubstituted anthracenylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted pyridylene group; a substituted or unsubstituted pyrimidylene group; a substituted or unsubstituted quinolinylene group; a substituted or unsubstituted isoquinolinylene group; a substituted or unsubstituted dibenzofuranylene group; a substituted or unsubstituted dibenzothiophenylene group; a substituted or unsubstituted benzofuropyridylene group; or a substituted or unsubstituted benzothiolopyridylene group.

[0129] In one embodiment of the present application, Ra in chemical formula 1 may be hydrogen.

[0130] In one embodiment of the present application, Ra in chemical formula 1 may be deuterium.

[0131] In one embodiment of the present application, Ra of chemical formula 1 may be a group represented by the following chemical formula A.

[0132] In one embodiment of the present application, L2 of chemical formula A may be a single bond; a substituted or unsubstituted C6 to C40 arylene group; or a substituted or unsubstituted C2 to C40 heteroarylene group.

[0133] In one embodiment of the present application, L2 of chemical formula A may be a single bond; a substituted or unsubstituted C6 to C30 arylene group; or a substituted or unsubstituted C2 to C30 heteroarylene group.

[0134] In one embodiment of the present application, L2 of chemical formula A may be a single bond; a substituted or unsubstituted C6 to C20 arylene group; or a substituted or unsubstituted C2 to C20 heteroarylene group.

[0135] In one embodiment of the present application, L2 of chemical formula A may be a single bond; a substituted or unsubstituted C6 to C10 arylene group; or a substituted or unsubstituted C2 to C10 heteroarylene group.

[0136] In one embodiment of the present application, L2 of chemical formula A may 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 naphthylene group; a substituted or unsubstituted anthracenylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted pyridylene group; a substituted or unsubstituted pyrimidylene group; a substituted or unsubstituted quinolinylene group; a substituted or unsubstituted isoquinolinylene group; a substituted or unsubstituted dibenzofuranylene group; a substituted or unsubstituted dibenzothiophenylene group; a substituted or unsubstituted benzofuropyridylene group; or a substituted or unsubstituted benzothiolopyridylene group.

[0137] In one embodiment of the present application, Ar2 of chemical formula A may be a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0138] In one embodiment of the present application, Ar2 of chemical formula A may be a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0139] In one embodiment of the present application, Ar2 of chemical formula A may be a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0140] In one embodiment of the present application, Ar2 of chemical formula A may be a substituted or unsubstituted C6 to C10 aryl group; or a substituted or unsubstituted C2 to C10 heteroaryl group.

[0141] In one embodiment of the present application, Ar2 of chemical formula A may be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group; a substituted or unsubstituted pyrimidyl group; a substituted or unsubstituted quinolinyl group; a substituted or unsubstituted isoquinolinyl group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted dibenzothiophenyl group; a substituted or unsubstituted benzofuropyridyl group; or a substituted or unsubstituted benzothiolopyridyl group. In one embodiment of the present application, Ar1 of chemical formula 1 may be a group represented by the following chemical formula 2.

[0142] In one embodiment of the present application, Ar1 of chemical formula 1 may be a group represented by the following chemical formula 3.

[0143] In one embodiment of the present application, R1 and R2 in chemical formula 2 are the same as or different from each other, and each independently hydrogen; deuterium; a cyano group; a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C2 to C40 alkenyl group; a substituted or unsubstituted C2 to C40 alkynyl group; a substituted or unsubstituted C1 to C40 alkoxy group; a substituted or unsubstituted C3 to C40 cycloalkyl group; a substituted or unsubstituted C2 to C40 heterocycloalkyl group; a substituted or unsubstituted C6 to C40 aryl group; a substituted or unsubstituted C2 to C40 heteroaryl group; -P(=O)R101R102 and -SiR101R102R103, or two or more adjacent groups are combined to form a substituted or unsubstituted C6 to C40 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C40 heterocycle, wherein R101, R102 and R103 are the same or different, and each independently represent a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0144] In one embodiment of the present application, R1 and R2 in chemical formula 2 are the same as or different from each other, and each independently represent hydrogen; deuterium; a cyano group; a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C2 to C30 alkenyl group; a substituted or unsubstituted C2 to C30 alkynyl group; a substituted or unsubstituted C1 to C30 alkoxy group; a substituted or unsubstituted C3 to C30 cycloalkyl group; a substituted or unsubstituted C2 to C30 heterocycloalkyl group; a substituted or unsubstituted C6 to C30 aryl group; a substituted or unsubstituted C2 to C30 heteroaryl group; -P(=O)R101R102 and -SiR101R102R103, or two or more adjacent groups are combined to form a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C30 heterocycle, wherein R101, R102 and R103 are the same or different, and each independently represent a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0145] In one embodiment of the present application, R1 and R2 in chemical formula 2 are the same as or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; a cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C2 to C20 alkenyl group; a substituted or unsubstituted C2 to C20 alkynyl group; a substituted or unsubstituted C1 to C20 alkoxy group; a substituted or unsubstituted C3 to C20 cycloalkyl group; a substituted or unsubstituted C2 to C20 heterocycloalkyl group; a substituted or unsubstituted C6 to C20 aryl group; and a substituted or unsubstituted C2 to C20 heteroaryl group, or two or more adjacent groups may combine with each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C20 heterocycle.

[0146] In one embodiment of the present application, R1 and R2 in chemical formula 2 are the same as or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; a cyano group; a substituted or unsubstituted C1 to C10 alkyl group; a substituted or unsubstituted C2 to C10 alkenyl group; a substituted or unsubstituted C2 to C10 alkynyl group; a substituted or unsubstituted C1 to C10 alkoxy group; a substituted or unsubstituted C3 to C10 cycloalkyl group; a substituted or unsubstituted C2 to C10 heterocycloalkyl group; a substituted or unsubstituted C6 to C10 aryl group; and a substituted or unsubstituted C2 to C10 heteroaryl group, or two or more adjacent groups may combine with each other to form a substituted or unsubstituted C6 to C10 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C10 heterocycle.

[0147] In one embodiment of the present application, R1 and R2 in Chemical Formula 2 may be the same as or different from each other, and each independently be a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted propyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group; a substituted or unsubstituted pyrimidyl group; a substituted or unsubstituted quinolinyl group; a substituted or unsubstituted isoquinolinyl group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted dibenzothiophenyl group; a substituted or unsubstituted benzofuropyridyl group; or a substituted or unsubstituted benzothiolopyridyl group.

[0148] In one embodiment of the present application, L3 in chemical formula 3 may be the same as or different from each other, and may each independently be a single bond; a substituted or unsubstituted C6 to C40 arylene group; or a substituted or unsubstituted C2 to C40 heteroarylene group.

[0149] In one embodiment of the present application, L3 in chemical formula 3 may be the same as or different from each other, and may each independently be a single bond; a substituted or unsubstituted C6 to C30 arylene group; or a substituted or unsubstituted C2 to C30 heteroarylene group.

[0150] In one embodiment of the present application, L3 in chemical formula 3 may be the same as or different from each other, and may each independently be a single bond; a substituted or unsubstituted C6 to C20 arylene group; or a substituted or unsubstituted C2 to C20 heteroarylene group.

[0151] In one embodiment of the present application, L3 in chemical formula 3 may be the same as or different from each other, and may each independently be a single bond; a substituted or unsubstituted C6 to C10 arylene group; or a substituted or unsubstituted C2 to C10 heteroarylene group.

[0152] In one embodiment of the present application, L3 in chemical formula 3 may be the same as or different from each other, and 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 naphthylene group; a substituted or unsubstituted anthracenylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted pyridylene group; a substituted or unsubstituted pyrimidylene group; a substituted or unsubstituted quinolinylene group; a substituted or unsubstituted isoquinolinylene group; a substituted or unsubstituted dibenzofuranylene group; a substituted or unsubstituted dibenzothiophenylene group; a substituted or unsubstituted benzofuropyridylene group; or a substituted or unsubstituted benzothiolopyridylene group.

[0153] In one embodiment of the present application, R3 in chemical formula 3 is the same as or different from each other, and each independently represents hydrogen; deuterium; a cyano group; a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C2 to C40 alkenyl group; a substituted or unsubstituted C2 to C40 alkynyl group; a substituted or unsubstituted C1 to C40 alkoxy group; a substituted or unsubstituted C3 to C40 cycloalkyl group; a substituted or unsubstituted C2 to C40 heterocycloalkyl group; a substituted or unsubstituted C6 to C40 aryl group; a substituted or unsubstituted C2 to C40 heteroaryl group; -P(=O)R101R102 and -SiR101R102R103, or two or more adjacent groups are combined to form a substituted or unsubstituted C6 to C40 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C40 heterocycle, wherein R101, R102 and R103 are the same or different, and each independently represent a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0154] In one embodiment of the present application, R3 in chemical formula 3 is the same as or different from each other, and each independently represents hydrogen; deuterium; a cyano group; a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C2 to C30 alkenyl group; a substituted or unsubstituted C2 to C30 alkynyl group; a substituted or unsubstituted C1 to C30 alkoxy group; a substituted or unsubstituted C3 to C30 cycloalkyl group; a substituted or unsubstituted C2 to C30 heterocycloalkyl group; a substituted or unsubstituted C6 to C30 aryl group; a substituted or unsubstituted C2 to C30 heteroaryl group; -P(=O)R101R102 and -SiR101R102R103, or two or more adjacent groups are combined to form a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C30 heterocycle, wherein R101, R102 and R103 are the same or different, and each independently represent a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0155] In one embodiment of the present application, R3 in chemical formula 3 is the same as or different from each other, and each independently selected from the group consisting of hydrogen; deuterium; a cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C2 to C20 alkenyl group; a substituted or unsubstituted C2 to C20 alkynyl group; a substituted or unsubstituted C1 to C20 alkoxy group; a substituted or unsubstituted C3 to C20 cycloalkyl group; a substituted or unsubstituted C2 to C20 heterocycloalkyl group; a substituted or unsubstituted C6 to C20 aryl group; and a substituted or unsubstituted C2 to C20 heteroaryl group, or two or more adjacent groups may combine with each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C20 heterocycle.

[0156] In one embodiment of the present application, R3 in chemical formula 3 is the same as or different from each other, and each independently selected from the group consisting of hydrogen; deuterium; a cyano group; a substituted or unsubstituted C1 to C10 alkyl group; a substituted or unsubstituted C2 to C10 alkenyl group; a substituted or unsubstituted C2 to C10 alkynyl group; a substituted or unsubstituted C1 to C10 alkoxy group; a substituted or unsubstituted C3 to C10 cycloalkyl group; a substituted or unsubstituted C2 to C10 heterocycloalkyl group; a substituted or unsubstituted C6 to C10 aryl group; and a substituted or unsubstituted C2 to C10 heteroaryl group, or two or more adjacent groups may combine with each other to form a substituted or unsubstituted C6 to C10 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C10 heterocycle.

[0157] In one embodiment of the present application, R3 in chemical formula 3 may be the same as or different from each other, and each independently be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyridyl group; a substituted or unsubstituted pyrimidyl group; a substituted or unsubstituted quinolinyl group; a substituted or unsubstituted isoquinolinyl group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted dibenzothiophenyl group; a substituted or unsubstituted benzofuropyridyl group; or a substituted or unsubstituted benzothiolopyridyl group.

[0158] In one embodiment of the present application, the chemical formula 1 may be represented by either the following chemical formula 1-1 or chemical formula 1-2.

[0159] [Chemical Formula 1-1]

[0160]

[0161] [Chemical Formula 1-2]

[0162]

[0163] In the above chemical formulas 1-1 and 1-2, the definition of each substituent is the same as in chemical formula 1.

[0164] In one embodiment of the present application, the chemical formula 1 may be represented by any one of the following chemical formulas 1-1A to 1-2D.

[0165] [Chemical Formula 1-1A]

[0166]

[0167] [Chemical Formula 1-1B]

[0168]

[0169] [Chemical Formula 1-1C]

[0170]

[0171] [Chemical Formula 1-1D]

[0172]

[0173] [Chemical Formula 1-2A]

[0174]

[0175] [Chemical Formula 1-2B]

[0176]

[0177] [Chemical Formula 1-2C]

[0178]

[0179] [Chemical Formula 1-2D]

[0180]

[0181] In the above chemical formulas 1-1A to 1-2D, the definition of each substituent is the same as in chemical formula 1.

[0182] In one embodiment of the present application, the heterocyclic compound represented by the chemical formula 1 may not contain deuterium as a substituent, or the content of deuterium may be, for example, 1% or more, 5% or more, 10% or more, 15% or more, 20% or more, 25% or more, 30% or more, 35% or more, 40% or more, 45% or more, or 50% or more, and may be 100% or less, 95% or less, 90% or less, 85% or less, 80% or less, 75% or less, 70% or less, 65% or less, or 60% or less, based on the total number of hydrogen atoms and deuterium atoms.

[0183] In one embodiment of the present application, the heterocyclic compound represented by the chemical formula 1 may not contain deuterium, or may have a deuterium content of 1% to 100% based on the total number of hydrogen atoms and deuterium atoms.

[0184] In one embodiment of the present application, the heterocyclic compound represented by the chemical formula 1 may not contain deuterium, or may have a deuterium content of 10% to 100% based on the total number of hydrogen atoms and deuterium atoms.

[0185] In one embodiment of the present application, the heterocyclic compound represented by the chemical formula 1 may not contain deuterium, or may have a deuterium content of 20% to 90% based on the total number of hydrogen atoms and deuterium atoms.

[0186] In one embodiment of the present application, the heterocyclic compound represented by the chemical formula 1 may not contain deuterium, or may have a deuterium content of 30% to 80% based on the total number of hydrogen atoms and deuterium atoms.

[0187] In one embodiment of the present application, the heterocyclic compound represented by the chemical formula 1 may not contain deuterium, or may have a deuterium content of 40% to 70% based on the total number of hydrogen atoms and deuterium atoms.

[0188] In one embodiment of the present application, the heterocyclic compound represented by the chemical formula 1 may not contain deuterium, or may have a deuterium content of 50% to 60% based on the total number of hydrogen atoms and deuterium atoms.

[0189] In one embodiment of the present application, the chemical formula 1 provides a heterocyclic compound represented by any one of the compounds below. In addition, in one embodiment of the present application, the compounds below are only examples, and are not limited thereto, and other compounds included in chemical formula 1 that include additional substituents may be included.

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204] In addition, by introducing various substituents into the structure of the above chemical formula 1, it is possible to synthesize compounds having the unique characteristics of the introduced substituents. For example, by introducing substituents mainly used in hole injection layer materials, hole transport materials, light-emitting layer materials, electron transport layer materials, and charge generation layer materials used in the manufacture of organic light-emitting devices into the core structure, it is possible to synthesize materials that satisfy the conditions required for each organic layer.

[0205] In addition, by introducing various substituents into the structure of the above chemical formula 1, it is possible to finely control the energy band gap, while improving the properties at the interface between organic substances and diversifying the uses of the material.

[0206] Another embodiment of the present invention provides an organic light-emitting device comprising a heterocyclic compound represented by the above chemical formula 1. The "organic light-emitting device" may be expressed by terms such as "organic light-emitting diode", "OLED (Organic Light Emitting Diodes)", "OLED device", and "organic electroluminescent device".

[0207] In one embodiment of the present application, an organic light-emitting device is provided, comprising: a first electrode; a second electrode provided opposite the first electrode; and one or more organic layers provided between the first electrode and the second electrode; wherein at least one of the organic layers includes a heterocyclic compound represented by the chemical formula 1.

[0208] In one embodiment of the present application, the first electrode may be an anode, and the second electrode may be a cathode.

[0209] In another embodiment, the first electrode may be a cathode and the second electrode may be an anode.

[0210] In one embodiment of the present application, the organic light-emitting device may be a blue organic light-emitting device, and the heterocyclic compound according to the chemical formula 1 may be used as a material of the blue organic light-emitting device.

[0211] In one embodiment of the present application, the organic light-emitting device may be a green organic light-emitting device, and the heterocyclic compound represented by the chemical formula 1 may be used as a material of the green organic light-emitting device.

[0212] In one embodiment of the present application, the organic light-emitting device may be a red organic light-emitting device, and the heterocyclic compound represented by the chemical formula 1 may be used as a material of the red organic light-emitting device.

[0213] The specific details of the heterocyclic compound represented by the above chemical formula 1 are the same as described above.

[0214] The organic light-emitting device of the present invention can be manufactured using a conventional method and material for manufacturing an organic light-emitting device, except that one or more organic layers are formed using the aforementioned heterocyclic compound.

[0215] The above heterocyclic compound can be formed into an organic layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light-emitting device. Here, the solution coating method refers to, but is not limited to, spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc.

[0216] The organic layer of the organic light-emitting device of the present invention may be formed as a single-layer structure, but may also be formed as a multi-layer structure in which two or more organic layers are laminated. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as the organic layers. However, the structure of the organic light-emitting device is not limited thereto and may include a smaller number of organic layers.

[0217] In the organic light-emitting device of the present invention, the organic layer includes an electron injection layer or an electron transport layer, and the electron injection layer or the electron transport layer may include the heterocyclic compound.

[0218] In the organic light-emitting device of the present invention, the organic layer includes an electron transport layer, and the electron transport layer may include the heterocyclic compound.

[0219] In another organic light-emitting device, the organic layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer may include the heterocyclic compound.

[0220] In another organic light-emitting device, the organic layer includes a hole-blocking layer, and the hole-blocking layer may include the heterocyclic compound.

[0221] In another organic light-emitting device, the organic layer includes an electron transport layer, an emission layer, or a hole blocking layer, and the electron transport layer, the emission layer, or the hole blocking layer may include the heterocyclic compound.

[0222] 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, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

[0223] The stacking order of electrodes and organic layers of an organic light-emitting device according to one embodiment of the present application is exemplified in Figures 1 to 3. However, the scope of the present application is not intended to be limited by these drawings, and the structure of an organic light-emitting device known in the art may also be applied to the present application.

[0224] According to FIG. 1, an organic light-emitting device is illustrated in which an anode (200), an organic layer (300), and a cathode (400) are sequentially laminated on a substrate (100). However, the present invention is not limited to this structure, and an organic light-emitting device in which a cathode, an organic layer, and an anode are sequentially laminated on a substrate, as shown in FIG. 2, may also be implemented.

[0225] Fig. 3 illustrates a case where the organic layer is multilayered. The organic light-emitting device according to Fig. 3 includes a hole injection layer (301), a hole transport layer (302), a light-emitting layer (303), a hole blocking layer (304), an electron transport layer (305), and an electron injection layer (306). However, the scope of the present application is not limited by such a laminated structure, and, if necessary, the remaining layers except for the light-emitting layer may be omitted, and other necessary functional layers may be further added.

[0226] The organic layer containing the above chemical formula 1 may additionally contain other substances as needed.

[0227] In addition, an organic light-emitting device according to one embodiment of the present application includes an anode, a cathode, and two or more stacks provided between the anode and the cathode, wherein the two or more stacks each independently include a light-emitting layer, and a charge generation layer is included between the two or more stacks, and the charge generation layer includes a heterocyclic compound represented by the chemical formula 1.

[0228] In addition, an organic light-emitting device according to one embodiment of the present application includes an anode, a first stack provided on the anode and including a first light-emitting layer, a charge generation layer provided on the first stack, a second stack provided on the charge generation layer and including a second light-emitting layer, and a cathode provided on the second stack. At this time, the charge generation layer may include a heterocyclic compound represented by the chemical formula 1. In addition, the first stack and the second stack may each independently additionally include one or more of the aforementioned hole injection layer, hole transport layer, hole blocking layer, electron transport layer, electron injection layer, etc.

[0229] The charge generation layer may be an N-type charge generation layer, and the charge generation layer may additionally include a dopant known in the art in addition to the heterocyclic compound represented by chemical formula 1.

[0230] As an organic light-emitting device according to one embodiment of the present application, an organic light-emitting device having a 2-stack tandem structure is schematically illustrated in FIG. 4 below.

[0231] At this time, the first electron blocking layer, the first hole blocking layer, and the second hole blocking layer described in the above drawing 4 may be omitted depending on the case.

[0232] In the organic light-emitting device according to one embodiment of the present application, materials other than the compound of the above chemical formula 1 are exemplified below, but these are only for exemplification and are not intended to limit the scope of the present application, and may be replaced with materials known in the art.

[0233] Materials having a relatively large work function can be used as the anode material, and transparent conductive oxides, metals, or conductive polymers can be used. Specific examples of the anode material include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline.

[0234] Materials with relatively low work functions can be used as cathode materials, and metals, metal oxides, or conductive polymers can be used. Specific examples of the cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayered materials such as LiF / Al or LiO2 / Al.

[0235] As the hole injection material, a known hole injection material may be used, for example, a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429, or a starburst amine derivative described in the literature [Advanced Material, 6, p. 677 (1994)], such as tris(4-carbazoyl-9-ylphenyl)amine (TCTA), 4,4',4″-tri[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB), a soluble conductive polymer such as polyaniline / dodecylbenzenesulfonic acid, or Poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate), polyaniline / camphor sulfonic acid, or polyaniline / poly(4-styrene-sulfonate) can be used.

[0236] Pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, etc. can be used as hole transport materials, and low molecular weight or high molecular weight materials can also be used.

[0237] As the electron transport material, metal complexes of oxadiazole derivatives, anthraquinodimethane and derivatives thereof, benzoquinone and derivatives thereof, naphthoquinone and derivatives thereof, anthraquinone and derivatives thereof, tetracyanoanthraquinodimethane and derivatives thereof, fluorenone derivatives, diphenyldicyanoethylene and derivatives thereof, diphenoquinone derivatives, 8-hydroxyquinoline and derivatives thereof, etc. can be used, and not only low molecular weight substances but also high molecular weight substances can be used.

[0238] For example, LiF is a representative material used in the art, but the present application is not limited thereto.

[0239] Red, green, or blue light-emitting materials may be used as the light-emitting material, and if necessary, two or more light-emitting materials may be mixed and used. At this time, two or more light-emitting materials may be deposited and used as individual sources, or may be premixed and deposited and used as a single source. In addition, a fluorescent material may be used as the light-emitting material, but it may also be used as a phosphorescent material. A material that emits light by combining holes and electrons injected from the anode and cathode, respectively, may be used as the light-emitting material, but materials in which both the host material and the dopant material participate in light emission may also be used.

[0240] When using a mixture of hosts for light-emitting materials, hosts of the same series may be mixed and used, or hosts of different series may be mixed and used. For example, two or more types of materials, either n-type host materials or p-type host materials, may be selected and used as the host materials for the light-emitting layer.

[0241] An organic light-emitting device according to one embodiment of the present application may be a front-emitting, back-emitting, or double-sided emitting type depending on the material used.

[0242] The heterocyclic compound according to one embodiment of the present application can function in organic electronic devices, including organic solar cells, organic photoconductors, organic transistors, etc., using a principle similar to that applied to organic light-emitting devices.

[0243] Hereinafter, preferred examples are presented to help understand the present invention, but the following examples are provided only to make it easier to understand the present invention and the present invention is not limited thereto.

[0244]

[0245] <Manufacturing Example>

[0246] <Manufacturing Example 1> Preparation of compound 001

[0247]

[0248]

[0249] 1) Preparation of compound 001-P1

[0250] Compounds 2,4-Dichloroquinazoline (10 g, 50.24 mmol, 1 eq), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,10-phenanthroline (A) (16.15 g, 52.75 mmol, 1.05 eq), NaOH (13.89 g, 100.48 mmol, 2 eq), Pd(PPh3)4 (2.9 g, 2.51 mmol, 0.05 eq), 1,4-dioxane (120 ml), and water (30 ml) were added and stirred at 120°C for 6 hours. After quenching the reaction by adding water, extraction was performed using ethyl acetate and water. After that, moisture was removed with MgSO4. Compound 001-P1 (13.8 g) was obtained with a yield of 80.13% by separation using a silica gel column.

[0251]

[0252] 2) Preparation of compound 001

[0253] Compound 001-P1 (13 g, 37.93 mmol, 1 eq), 2-dibenzothiophen-4-yl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (B) (12.35 g, 39.82 mmol, 1.05 eq), Pd(PPh3)4 (2.19 g, 1.9 mmol, 0.05 eq), NaOH (10.48 g, 75.85 mmol, 2 eq), 1,4-dioxane (160 ml), and water (40 ml) were added and stirred at 120°C for 6 hours. Water was added to terminate the reaction, and extraction was performed using ethyl acetate and water. After that, moisture was removed with MgSO4. Compound 001 was obtained in a yield of 14.2 g (76.32%) by separation using a silica gel column.

[0254]

[0255] <Manufacturing Example 2> Manufacture of compounds 006, 011, 015, 017, 025, 031, 034, 038, 044, 046, 051, 056, 058, 062, 065, 076, 077, 084, 085, 090, 095, 098, 103, 109, 114, 119, 122, 127, 130, 135, 138, 143, 148, 151, 154, 162, 167, 170, 175, 179, 182, 199, 231, 246, and 252

[0256] In the above Preparation Example 1, instead of 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,10-phenanthroline (A), intermediate B was used instead of intermediate A, 2-dibenzothiophen-4-yl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (B) in Table 1 below, compounds 006, 011, 015, 017, 025, 031, 034, 038, 044, 046, 051, 056, 058, 062, 065, 076, 077, 084, 085, 090, 095, 098, 103, 109, 114, 119, 122, 127, 130, 135, 138, 143, 148, 151, 154, 162, 167, 170, 175, 179, 182, 199, 231, 246, and 252 were synthesized.

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265] The remaining compounds other than those described in Manufacturing Examples 1 and 2 and Table 1 were also manufactured using the same method as described in the above Manufacturing Examples, and the results of their synthesis are shown in Tables 2 and 3 below. Table 2 1The values ​​are measured by H NMR (CDCl3, 400 MHz), and Table 3 is measured by FD-mass spectrometry (FD-MS: Field desorption mass spectrometry).

[0266]

[0267]

[0268]

[0269]

[0270] 화합물FD-MS화합물FD-MS001m / z= 490.58(C32H18N4S= 490.13)006m / z= 566.68(C38H22N4S= 566.16)011m / z= 567.67(C37H21N5S= 567.15)015m / z= 692.84(C48H28N4S= 692.20)017m / z= 644.76 (C42H24N6S= 644.18)025m / z=643.77(C43H25N5S=643.18)031m / z= 588.66 (C38H25N2OPS=588.14)034m / z=588.66(C38H25N2OPS=588.14)038m / z=638.72 (C42H27N2OPS=638.16)044m / z=588.66(C38H25N2OPS=588.14)046m / z=474.52 (C32H18N4O=474.15)051m / z=550.62(C38H22N4O=550.18)056m / z=600.68 (C42H24N4O=600.20)058m / z=626.72(C44H26N4O= 626.21)062m / z= 676.78 (C48H28N4O= 676.23)065m / z= 677.77(C47H27N5O= 677.22)076m / z= 572.60 (C38H25N2O2P= 572.17)077m / z= 572.60(C38H25N2O2P= 572.17)084m / z= 622.66 (C42H27N2O2P= 622.18)085m / z= 572.60(C38H25N2O2P= 572.17)090m / z= 490.58 (C32H18N4S= 490.13)095m / z= 566.68(C38H22N4S= 566.16)098m / z= 567.67 (C37H21N5S= 567.15)103m / z= 566.68(C38H22N4S= 566.16)109m / z= 642.78 (C44H26N4S= 642.19)114m / z= 567.67(C37H21N5S= 567.15)119m / z= 512.57 (C32H21N2OPS= 512.11)122m / z= 588.66(C38H25N2OPS= 588.14)127m / z= 638.72 (C42H27N2OPS= 638.16)130m / z= 588.66(C38H25N2OPS= 588.14)135m / z= 474.52 (C32H18N4O= 474.15)138m / z= 550.62(C38H22N4O= 550.18)143m / z= 551.61 (C37H21N5O= 551.17)148m / z= 676.78(C48H28N4O= 676.23)151m / z= 550.62 (C38H22N4O= 550.18)154m / z= 626.72(C44H26N4O= 626.21)162m / z= 572.60 (C38H25N2O2P=572.17)167m / z= 572.60 (C38H25N2O2P=572.17)170m / z= 622.66 (C42H27N2O2P=622.18)175m / z= 572.60 (C38H25N2O2P=572.17)179m / z= 642.78 (C44H26N4S=642.19)182m / z= 692.84 (C48H28N4S= 692.20)199m / z= 648.70 (C44H29N2O2P= 648.20)231m / z=752.88(C54H32N4O= 752.26)246m / z= 740.86 (C50H33N2OPS= 740.21)252m / z= 513.55(C54H32N4O= 513.11).

[0271]

[0272] <실호예 1>

[0273] 1) Organic production

[0274] An indium tin oxide (ITO) thin film for a transparent electrode obtained from glass for OLED (manufactured by Samsung Corning) was ultrasonically cleaned sequentially using trichloroethylene, acetone, ethanol, and distilled water for 5 minutes each, and then stored in isopropanol before use. Next, the ITO substrate was installed in the substrate folder of the vacuum deposition equipment, and 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenyl amine (4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenyl amine: 2-TNATA) was added to the cell in the vacuum deposition equipment.

[0275]

[0276] Then the vacuum level inside the chamber is 10 -6 After evacuating to 10 torr, a current was applied to the cell to evaporate 2-TNATA, thereby depositing a hole injection layer with a thickness of 600 Å on an ITO substrate. N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) was placed in another cell within the vacuum deposition equipment, and a current was applied to the cell to evaporate the NPB, thereby depositing a hole transport layer with a thickness of 300 Å on the hole injection layer.

[0277]

[0278] After forming the hole injection layer and the hole transport layer in this way, a blue light-emitting material having the following structure was deposited as a light-emitting layer thereon. Specifically, a blue light-emitting host material, H1, was vacuum-deposited to a thickness of 200 Å in one cell within a vacuum deposition device, and a blue light-emitting dopant material, D1, was vacuum-deposited thereon at a thickness of 5% relative to the host material.

[0279]

[0280] Next, a compound of the following structural formula E1 was deposited as an electron transport layer with a thickness of 300 Å.

[0281]

[0282] An OLED device was fabricated by depositing lithium fluoride (LiF) as an electron injection layer with a thickness of 10 Å and using an Al cathode with a thickness of 1,000 Å. Meanwhile, all organic compounds required for fabricating an OLED device were each 10 Å thick. -8 ~10 -6 It was purified by vacuum sublimation under 10 torr and used in OLED production.

[0283] An organic electroluminescent device was manufactured in the same manner as in Comparative Example 1, except that the compound shown in Table 4 below was used instead of E1 used in forming the electron transport layer in Comparative Example 1.

[0284]

[0285] 2) Driving voltage and luminous efficiency of organic electroluminescent devices

[0286] The electroluminescence (EL) characteristics of the organic light-emitting devices manufactured as described above were measured using the M7000 from MaxScience, and the standard luminance was determined to be 3,500 cd / m using the lifespan measurement equipment (M6000) manufactured by MaxScience based on the measurement results. 2 The lifespan T is the time it takes for the initial luminance to reach 95% of its original brightness. 95 (Unit: h, time) was measured. The results of measuring the driving voltage, luminous efficiency, and lifespan of the organic light-emitting device of the present invention as shown in the above measurement results are as shown in Table 4 below.

[0287] Compound Driving Voltage (V) Luminous Efficiency (cd / A) CIE (x, y) Lifetime (T 95) Example 10014.806.91(0.133, 0.100)90 Example 20064.846.88(0.134, 0.100)91 Example 30114.856.80(0.134, 0.100)89 Example 40154.806.83(0.134, 0.101)88 Example 50174.876.84(0.133, 0.101)85 Example 60254.816.85(0.134, 0.100)90 Example 70314.856.90(0.133, 0.101)89 Example 80344.806.74(0.134, 0.100)92 Example 90384.826.88(0.133, 0.100)89 Example 100444.866.80(0.133, 0.101)87 Example 110464.846.70(0.133, 0.100)92 Example 120514.836.91(0.133, 0.100)91 Example 130564.826.85(0.134, 0.100)85 Example 140584.836.84(0.133, 0.100)86 Example 150624.816.86(0.133, 0.101)88 Example 160654.856.87(0.134, 0.101)84 Example 170764.806.88(0.133, 0.100)90 Example 180774.836.85(0.133, 0.101)88 Example 190844.866.87(0.134, 0.100)85 Example 200854.916.76(0.134, 0.100)86 Example 210904.826.90(0.133, 0.101)85 Example 220954.866.88(0.134, 0.101)88Comparative Example 1E15.516.17(0.134, 0.100)31Comparative Example 2Comparative Compound A4.986.52(0.133, 0.100)69Comparative Example 3Comparative Compound B5.016.48(0.133, 0.100)66Comparative Example 4Comparative Compound C5.236.34(0.134, 0.100)68Comparative Example 5Comparative Compound D5.306.29(0.133, 0.101)59Comparative Example 6Comparative Compound E5.366.11(0.133, 0.101)64Comparative Example 7Comparative Compound F5.226.22(0.133, 0.100)60

[0288]

[0289] The comparative compounds used in Table 4 above are as follows.

[0290]

[0291] As can be seen from the results in Table 4 above, the organic light-emitting device using the electron transport layer material of the blue organic light-emitting device of the present invention has a lower driving voltage and significantly improved luminous efficiency and lifespan compared to Comparative Examples 1 to 7.

[0292] The reason for these results is that structures in which an azine substituent is connected, such as in Comparative Example 3, or structures in which a phenanthroline group or a phosphine oxide group is not connected, such as in Comparative Example 4, have difficulty in exhibiting appropriate physical properties as an electron transport layer, and when the phenanthroline substituent is at a position such as in Comparative Example 2, it is judged that electron transport characteristics that are not appropriate for the organic light-emitting device of the present invention are exhibited.

[0293] In addition, the dibenzofuran or dibenzothiophene core of the heterocyclic compound represented by chemical formula 1 as in the present invention ( ) is judged to have a quinazoline group as the linking group connected to a phenanthroline group or a phosphine oxide group, thereby increasing the band gap by increasing the intermolecular π-π stacking compared to the pyrimidinyl group as the linking group of Comparative Example 5 and the phenylene group as the linking group of Comparative Example 7, thereby improving the electron transport ability.

[0294] Comparative Example 6 has two Ns in the benzene ring to which phenanthroline is not connected in the parent structure, but the compound of the present invention has two Ns in the quinazoline group, and when used as a material for an organic light-emitting device, it has the advantage of easily exhibiting appropriate physical properties as an electron transport layer by implementing a more suitable energy level.

[0295] Therefore, it is believed that the compound of the present invention has improved electron-transport characteristics or stability, thereby providing superiority in all aspects of operation, efficiency, and lifespan.

[0296]

[0297] Experimental Example 2

[0298] 1) Fabrication of organic light-emitting devices

[0299] A glass substrate coated with a 1,500 Å thick ITO film was ultrasonically cleaned in distilled water. After the distilled water cleaning, it was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UVO for 5 minutes in a UV cleaner. The substrate was then transferred to a plasma cleaner (PT), where it was plasma-treated in a vacuum to remove the ITO work function and residual film, and then transferred to a thermal evaporation device for organic deposition.

[0300] An organic material was formed in a 2-stack WOLED (White Organic Light Device) structure on the above ITO transparent electrode (anode). For the first stack, TAPC was first thermally vacuum-deposited to a thickness of 300 Å to form a hole transport layer. After forming the hole transport layer, an emission layer was thermally vacuum-deposited thereon as follows. The emission layer was deposited to a thickness of 300 Å by doping 8 wt% of FIrpic as a blue phosphorescent dopant into the host TCz1. The electron transport layer was formed to a thickness of 400 Å using TmPyPB, and then the N-type charge generation layer was formed to a thickness of 100 Å by doping 20% ​​of Cs2CO3 into the compound described in Table 5 below.

[0301] The second stack was first formed by thermally vacuum depositing MoO3 to a thickness of 50 Å to form a hole injection layer. The common layer, the hole transport layer, was formed by doping TAPC with 20% MoO3 to form 100 Å, and then depositing TAPC to a thickness of 300 Å. On top of that, the emission layer was formed by doping TCz1, the host, with 8 wt% of Ir(ppy)3, a green phosphorescent toppant, and depositing it to a thickness of 300 Å, and then using TmPyPB as the electron transport layer to form 600 Å. Finally, lithium fluoride (LiF) was deposited to a thickness of 10 Å on the electron transport layer to form an electron injection layer, and then an aluminum (Al) cathode was deposited to a thickness of 1,200 Å on the electron injection layer to form a cathode, thereby manufacturing an organic electroluminescent device.

[0302] Meanwhile, all organic compounds required for OLED device production are 10 for each material. -8 ~10 -6 It was purified by vacuum sublimation under 10 torr and used in OLED production.

[0303]

[0304]

[0305] 2) Driving voltage and luminous efficiency of organic electroluminescent devices

[0306] The electroluminescence (EL) characteristics of the organic light-emitting devices manufactured as described above were measured using the M7000 from MaxScience, and the standard luminance was determined to be 3,500 cd / m using the lifespan measurement equipment (M6000) manufactured by MaxScience based on the measurement results. 2 The lifespan T is the time it takes for the initial luminance to reach 95% of its original brightness. 95 (Unit: h, time) was measured. The results of measuring the driving voltage, luminous efficiency, and lifespan of the white organic light-emitting device of the present invention as shown in the above measurement results are as shown in Table 5 below.

[0307] Compound Driving Voltage (V) Luminous Efficiency (cd / A) CIE (x, y) Lifetime (T 95) Example 23 0987.2169.53(0.215, 0.425) 86 Example 24 1037.3070.03(0.216, 0,424) 90 Example 25 1097.2469.87(0.210, 0.425) 88 Example 26 1147.2268.13(0.212, 0.418) 91 Example 27 1197.3269.00(0.211, 0.418) 87 Example 28 1227.2071.50(0.210, 0.413) 90 Example 29 1277.2270.72(0.209, 0.422) 89 Example 301307.3368.58(0.210, 0.428)86 Example 311357.3569.13(0.209, 0.428)87 Example 321387.2168.43(0.210, 0.425)91 Example 331437.2869.84(0.212, 0.423)90 Example 341487.3270.18(0.210, 0.426)92 Example 351517.2970.02(0.212, 0.424)93 Example 361547.2070.42(0.211, 0.425)88 Example 371627.2769.25(0.214, 0.420)89 Example 381677.3369.39(0.212, 0.418)86 Example 391707.2269.88(0.214, 0.428)87 Example 401757.3171.98(0.210, 0.424)90 Example 411797.2668.80(0.219, 0.426)94 Example 421827.3069.22(0.210, 0.424)95 Example 431997.2870.13(0.212, 0.422)92 Example 442317.2367.58(0.214, 0.423)88Example 452467.3069.77(0.213, 0.417)93Example 462527.4072.04(0.210, 0.425)88Comparative Example 8TmPyPB8.2057.71(0.211, 0.430)85Comparative Example 9Comparative Compound A7.6656.88(0.210, 0.425)65Comparative Example 10Comparative Compound B7.8857.31(0.209, 0.425)64Comparative Example 11Comparative Compound C7.9056.61(0.211, 0.428)59Comparative Example 12Comparative Compound D7.7558.30(0.209, 0.424)54Comparative Example 13Comparative Compound E7.8258.83(0.212, 0.426)50Comparative Example 14Comparative Compound F7.8657.88(0.209, 0.425)55.

[0308]

[0309] The comparative compounds used in Table 5 above are as follows.

[0310]

[0311]

[0312] As can be seen from the results in Table 5 above, the organic light-emitting device using the compound of the present invention as a charge generation layer material has a lower driving voltage and significantly improved lifespan and luminous efficiency compared to Comparative Examples 8 to 14. The reason for these results is that, compared to Comparative Examples 12, 13, and 14, the compound of the present invention has a structure suitable for binding to a metal while containing two Ns in the quinazoline group.

[0313] In addition, compound B used in Comparative Example 10 has a pyrimidinyl group as a linking group, and compound E used in Comparative Example 11 has a phenylene group as a linking group. In comparison, it is judged that a gap state at a more suitable level is expressed as a charge generation layer by having a quinazoline group as a linking group connected to a heteroaryl group and a phenanthroline group or a phosphine oxide group, as in the present invention.

[0314] Specifically, compared to the compound of the present invention in which a substituent is attached to the 9-position of phenanthroline, the structure in which a substituent is attached to the 4-position, as in Comparative Example 10, has a structural form in which doping does not occur easily. Due to this structural feature, when the compound used as an N-type charge generation layer is doped with a metal, it is thought that a gap state is stably formed within the N-type charge generation layer, and electrons generated from the P-type charge generation layer are easily injected into the electron transport layer through the gap state generated within the N-type charge generation layer. Therefore, it is believed that the driving voltage of the organic light-emitting device is lowered and the efficiency and lifespan are improved by enabling good electron injection and electron transfer from the P-type charge generation layer to the N-type charge generation layer.

[0315]

[0316] [Explanation of symbols]

[0317] 100: Substrate

[0318] 200: Bipolar

[0319] 300: Organic layer

[0320] 301: Hole injection layer

[0321] 302: Hole transport layer

[0322] 303: Emissive layer

[0323] 304: Hole blocking layer

[0324] 305: Electron transport layer

[0325] 306: Electron injection layer

[0326] 400: Cathode

Claims

1. A heterocyclic compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, X is O or S, Y1 to Y4 are the same or different from each other, and are each independently CRa or N, Ra is hydrogen; deuterium; or a group represented by the following chemical formula A, L1 is a single bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, Ar1 is a group represented by the following chemical formula 2 or chemical formula 3, m1 and n1 are equal to or different from each other and are each independently an integer from 0 to 4, If m1 is 2 or more, L1 is equal or different, If n1 is 2 or greater, Ar1 is equal or different, [Chemical Formula A] In the above chemical formula A, L2 is a single bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, Ar2 is a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group, m2 and n2 are equal to or different from each other and are each independently an integer from 0 to 4, If m2 is greater than or equal to 2, L2 is equal or different, If n2 is 2 or greater, Ar2 is equal or different, [Chemical formula 2] [Chemical Formula 3] In the above chemical formulas 2 and 3, R1 to R3 are the same as or different from each other, and are each independently hydrogen; deuterium; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R101R102; And -SiR101R102R103, or two or more adjacent groups are combined with 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 as or different from each other and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, L3 is a single bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, m3 is an integer from 0 to 4, n3 is an integer from 0 to 4, If m3 is 2 or greater, L3 is equal or different, If n3 is 2 or greater, Ar3 is equal or different.

2. In paragraph 1, The above chemical formula 1 is represented by either the following chemical formula 1-1 or chemical formula 1-2. Heterocyclic compounds: [Chemical Formula 1-1] [Chemical Formula 1-2] In the above chemical formulas 1-1 and 1-2, the definition of each substituent is the same as in chemical formula 1.

3. In paragraph 1, The above chemical formula 1 is represented by any one of the following chemical formulas 1-1A to 1-2D: Heterocyclic compounds: [Chemical Formula 1-1A] [Chemical Formula 1-1B] [Chemical Formula 1-1C] [Chemical Formula 1-1D] [Chemical Formula 1-2A] [Chemical Formula 1-2B] [Chemical Formula 1-2C] [Chemical Formula 1-2D] In the above chemical formulas 1-1A to 1-2D, the definition of each substituent is the same as in chemical formula 1.

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

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

6. First electrode; A second electrode provided opposite to the first electrode; and At least one organic layer provided between the first electrode and the second electrode; As an organic light-emitting device comprising: An organic light-emitting device, wherein the organic layer comprises at least one heterocyclic compound according to any one of claims 1 to 5.

7. In paragraph 6, An organic light-emitting device, wherein the organic layer includes a light-emitting layer, and the light-emitting layer includes the heterocyclic compound.

8. In paragraph 6, An organic light-emitting device, wherein the organic layer comprises an electron injection layer or an electron transport layer, and the electron injection layer or the electron transport layer comprises the heterocyclic compound.

9. In paragraph 6, An organic light-emitting device wherein the organic layer comprises an electron-blocking layer or a hole-blocking layer, and the electron-blocking layer or the hole-blocking layer comprises the heterocyclic compound.

10. In paragraph 6, The organic light-emitting device further comprises one or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

11. In paragraph 6, The organic light-emitting device comprises a first electrode, a first stack provided on the first electrode and including a first light-emitting layer, a charge generation layer provided on the first stack, a second stack provided on the charge generation layer and including a second light-emitting layer, and a second electrode provided on the second stack.

12. In paragraph 11, An organic light-emitting device wherein the charge generation layer comprises the heterocyclic compound.

13. In paragraph 11, An organic light-emitting device, wherein the charge generation layer is an N-type charge generation layer, and the charge generation layer includes the heterocyclic compound.

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