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

Abstract

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

Description

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

[0001] This application claims the benefit of priority to Korean Patent Application No. 10-2023-0168200, dated November 28, 2023, the entire disclosure of which is incorporated herein by reference.

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

[0003]

[0004] Organic light-emitting diodes are a type of self-luminous display device that have the advantages of a wide viewing angle, excellent contrast, and fast response speed.

[0005] Organic light-emitting devices have a structure in which an organic thin film is placed between two electrodes. When voltage is applied to an organic light-emitting device of this structure, electrons and holes injected from the two electrodes combine in the organic thin film, forming pairs and then disappearing, emitting light. The organic thin film may be composed of a single layer or multiple layers, as needed.

[0006] The material of the organic thin film may have a light-emitting function as needed. For example, the organic thin film material may be a compound that can form a light-emitting layer on its own, or a compound that can act as a host or dopant in a host-dopant light-emitting layer. In addition, the material of the organic thin film may be a compound that can perform roles such as hole injection, hole transport, electron blocking, hole blocking, electron transport, and electron injection.

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

[0008]

[0009] [Previous literature]

[0010] [Patent Document]

[0011] (Patent Document 1) U.S. Patent No. 4,356,429

[0012]

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

[0014]

[0015] To achieve the above purpose,

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

[0017] [Chemical Formula 1]

[0018]

[0019] In the above chemical formula 1,

[0020] The above X1 and X2 are different from each other and are each independently a direct bond; NAr1; or CRaRb,

[0021] Either of the above X1 and X2 is a direct bond,

[0022] The above R1 to R4, Ra and Rb are the same as or different from each other, and each independently hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R101R102; -SiR101R102R103; And -NR101R102, or two or more adjacent groups are combined to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same as or different from each other and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0023] The above a is an integer from 0 to 6, and when a is 2 or more, R1 is equal to or different from each other,

[0024] The above b is an integer from 0 to 3, and when b is 2 or greater, R3 are equal to or different from each other,

[0025] The above Ar1 is a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0026] The above L1 is a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group,

[0027] The above c is an integer from 0 to 5, and when c is 2 or greater, L1 are equal to or different from each other,

[0028] The above N-Het is a substituted or unsubstituted C2 to C60 monocyclic or polycyclic heterocyclic group containing two or more N.

[0029]

[0030] In addition, the present invention comprises a first electrode;

[0031] A second electrode provided opposite to the first electrode; and

[0032] An organic light-emitting device comprising at least one organic layer provided between the first electrode and the second electrode,

[0033] An organic light-emitting device is provided, wherein at least one of the organic layers comprises a heterocyclic compound represented by the chemical formula 1.

[0034]

[0035] In addition, the present invention provides an organic light-emitting device in which the organic material layer further includes a heterocyclic compound represented by the following chemical formula 3.

[0036] [Chemical Formula 3]

[0037]

[0038] In the above chemical formula 3,

[0039] wherein R31 and R32 are the same as or different from each other, and each independently represent hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R301R302; -SiR301R302R303; And -NR301R302, 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 R301, R302 and R303 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,

[0040] The above g is an integer from 0 to 3, and when g is 2 or greater, R31 are equal to or different from each other,

[0041] The above h is an integer from 0 to 5, and when h is 2 or greater, R32 are equal to or different from each other,

[0042] The above L31 to L34 are the same or different from each other, and each independently represents a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group,

[0043] The above i is an integer from 0 to 5, and when i is 2 or greater, L31 are equal to or different from each other,

[0044] The above j is an integer from 0 to 5, and when j is 2 or greater, L32 are equal to or different from each other,

[0045] The above k is an integer from 0 to 5, and when k is 2 or greater, L33 are equal to or different from each other,

[0046] The above l is an integer from 0 to 5, and when l is 2 or greater, L34 are equal to or different from each other,

[0047] The above Ar31 to Ar33 are the same as or different from each other, and each independently represents a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0048]

[0049] In addition, the present invention provides a composition for an organic layer comprising a heterocyclic compound represented by the above chemical formula 1 and a heterocyclic compound represented by the above chemical formula 3.

[0050]

[0051] The compound described herein can be used as an organic layer material of an organic light-emitting device. The compound can serve as a hole injection layer material, a hole transport layer material, a light-emitting layer material, an electron transport layer material, an electron injection layer material, etc. in the organic light-emitting device. In particular, the compound can be used as a light-emitting layer material of an organic light-emitting device, and the compound can be used alone as a light-emitting material, or can be used as a host material or dopant material of the light-emitting layer.

[0052] Specifically, the compound may be used alone as a light-emitting material, or as a host material or dopant material in a light-emitting layer. When the heterocyclic compound represented by the above chemical formula 1 is used in an organic layer, the driving voltage of the organic light-emitting device can be lowered, the light-emitting efficiency can be improved, and the lifespan characteristics can be improved.

[0053]

[0054] Figures 1 to 3 are schematic drawings each showing a laminated structure of an organic light-emitting device according to one embodiment of the present invention.

[0055] Hereinafter, the present invention will be described in more detail.

[0056]

[0057] 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.

[0058] In this specification, "substituted or unsubstituted" means deuterium; halogen; cyano group; straight or branched chain alkyl group having a carbon atom ... -SiRR'R"; -P(=O)RR'; is substituted or unsubstituted with one or more substituents selected from the group consisting of a C1 to C20 alkylamine group; a C6 to C60 monocyclic or polycyclic arylamine group; and a C2 to C60 monocyclic or polycyclic heteroarylamine group, or is substituted or unsubstituted with a substituent in which two or more substituents selected from the above-mentioned substituents are linked, wherein R, R' and R" are the same as or different from each other, and each independently represents a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0059] In this specification, halogen may be fluorine; chlorine; bromine; or iodine.

[0060] In the present specification, an alkyl group includes a straight or branched chain having 1 to 60 carbon atoms, and may be further substituted by another substituent. The alkyl group may have 1 to 60 carbon atoms, specifically 1 to 40 carbon atoms, and more specifically 1 to 20 carbon atoms. Specific examples include a methyl group; an ethyl group; an n-propyl group; an isopropyl group; an n-butyl group; an isobutyl group; a tert-butyl group; a sec-butyl group; a 1-methyl-butyl group; a 1-ethyl-butyl group; an n-pentyl group; an isopentyl group; a neopentyl group; a tert-pentyl group; an n-hexyl group; a 1-methylpentyl group; a 2-methylpentyl group; a 4-methyl-2-pentyl group; a 3,3-dimethylbutyl group; a 2-ethylbutyl group; a n-heptyl group; a 1-methylhexyl group; a cyclopentylmethyl group; a cyclohexylmethyl group; n-octyl group; tert-octyl group; 1-methylheptyl group; 2-ethylhexyl group; 2-propylpentyl group; n-nonyl group; 2,2-dimethylheptyl group; 1-ethyl-propyl group; 1,1-dimethyl-propyl group; isohexyl group; 4-methylhexyl group; 5-methylhexyl group, etc., but are not limited thereto.

[0061] In the present specification, an alkenyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted by another substituent. The alkenyl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 2 to 20 carbon atoms. Specific examples include a vinyl group; a 1-propenyl group; an isopropenyl group; a 1-butenyl group; a 2-butenyl group; a 3-butenyl group; a 1-pentenyl group; a 2-pentenyl group; a 3-pentenyl group; a 3-methyl-1-butenyl group; a 1,3-butadienyl group; an allyl group; a 1-phenylvinyl-1-yl group; a 2-phenylvinyl-1-yl group; a 2,2-diphenylvinyl-1-yl group; a 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl group; 2,2-bis(diphenyl-1-yl)vinyl-1-yl group; stilbenyl group; styrenyl group, etc., but are not limited thereto.

[0062] 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.

[0063] 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.

[0064] In the present specification, a cycloalkyl group includes a monocyclic or polycyclic group having 3 to 60 carbon atoms, and may be further substituted by another substituent. Here, polycyclic means a group in which a cycloalkyl group is directly connected to or condensed with another ring group. Here, the other ring group may be a cycloalkyl group, but may also be another type of ring group; for example, a heterocycloalkyl group; an aryl group; a heteroaryl group, etc. The cycloalkyl group may have 3 to 60 carbon atoms, specifically 3 to 40 carbon atoms, and more specifically 5 to 20 carbon atoms. Specifically, a cyclopropyl group; a cyclobutyl group; a cyclopentyl group; a 3-methylcyclopentyl group; a 2,3-dimethylcyclopentyl group; a cyclohexyl group; a 3-methylcyclohexyl group; a 4-methylcyclohexyl group; a 2,3-dimethylcyclohexyl group; a 3,4,5-trimethylcyclohexyl group; 4-tert-butylcyclohexyl group; cycloheptyl group; cyclooctyl group, etc., but are not limited thereto.

[0065] In the present specification, a heterocycloalkyl group includes O, S, Se, N or Si as a heteroatom, and includes a monocyclic or polycyclic group having 2 to 60 carbon atoms, and may be further substituted by another substituent. Here, polycyclic means a group in which a heterocycloalkyl group is directly connected to or condensed with another ring group. Here, the other ring group may be a heterocycloalkyl group, but may also be another type of ring group; for example, a cycloalkyl group; an aryl group; a heteroaryl group, etc. The heterocycloalkyl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 3 to 20 carbon atoms.

[0066] In the present specification, an aryl group includes a monocyclic or polycyclic ring having 6 to 60 carbon atoms, and may be further substituted by another substituent. Here, polycyclic means a group in which an aryl group is directly connected to or condensed with another ring group. Here, the other ring group may be an aryl group, but may also be another type of ring group; for example, a cycloalkyl group; a heterocycloalkyl group; a heteroaryl group, etc. The aryl group may include a spiro group. The aryl group may have 6 to 60 carbon atoms, specifically 6 to 40 carbon atoms, and more specifically 6 to 20 carbon atoms. Specific examples of the aryl group include a phenyl group; a biphenyl group; a triphenyl group; a naphthyl group; anthryl group; a chrysenyl group; a phenanthrenyl group; a perylenyl group; a fluoranthenyl group; a triphenylenyl group; a phenalenyl group; a pyrenyl group; a tetracenyl group; a pentacenyl group; a fluorenyl group; an indenyl group; Acenaphthylenyl group; benzofluorenyl group; spirobifluorenyl group; 2,3-dihydro-1H-indenyl group; and condensed ring groups thereof, but are not limited thereto.

[0067] In the present specification, the phosphine oxide group is represented by -P(=O)R101R102, where R101 and R102 are the same or different from each other, and each independently may be a substituent composed of at least one of hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; an aryl group; and a heterocyclic group. Specifically, it may be substituted with an aryl group, and the above-described examples may be applied to the aryl group. For example, the phosphine oxide group includes, but is not limited to, a diphenylphosphine oxide group; a dinaphthylphosphine oxide group, and the like.

[0068] 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.

[0069] In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be combined with each other to form a ring.

[0070] When the above fluorenyl group is substituted, It can be, but is not limited to, the following.

[0071] In the present specification, a spiro group is a group including a spiro structure and may have 15 to 60 carbon atoms. For example, the spiro group may include a structure in which a 2,3-dihydro-1H-indene group or a cyclohexane group is spiro-bonded to a fluorenyl group. Specifically, the following spiro group may include any one of the groups having the following structural formula.

[0072]

[0073] In the present specification, a heteroaryl group includes S; O; Se; N; or Si as a heteroatom, and includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted by another substituent. Here, the polycyclic ring means a group in which a heteroaryl group is directly connected to or condensed with another ring group. Here, the other ring group may be a heteroaryl group, but may also be another type of ring group, for example, a cycloalkyl group; a heterocycloalkyl group; an aryl group, etc. The heteroaryl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 3 to 25 carbon atoms.Specific examples of the above heteroaryl group include a pyridyl group; a pyrrolyl group; a pyrimidyl group; a pyridazinyl group; a furanyl group; a thiophenyl group; an imidazolyl group; a pyrazolyl group; an oxazolyl group; an isoxazolyl group; a thiazolyl group; an isothiazolyl group; a triazolyl group; a furazanyl group; an oxadiazolyl group; a thiadiazolyl group; a dithiazolyl group; a tetrazolyl group; a pyranyl group; a thiopyranyl group; a diazinyl group; an oxazinyl group; a thiazinyl group; a dioxynyl group; a triazinyl group; a tetrazinyl group; a quinolyl group; an isoquinolyl group; a quinazolinyl group; an isoquinazolinyl group; a quinozolinyl group; a naphthyridyl group; an acridinyl group; a phenanthridinyl group; an imidazopyridinyl group; a diazanaphthalenyl group; Triazaindenyl group; 2-indolyl group; indolizinyl group; benzothiazolyl group; benzoxazolyl group; benzimidazolyl group; benzothiophenyl group; benzofuranyl group; dibenzothiophenyl group; dibenzofuranyl group; carbazolyl group; benzocarbazolyl group; dibenzocarbazolyl group; phenazinyl group; dibenzosilole group; spirobi(dibenzosilole) group; dihydrophenazinyl group; phenoxazinyl group; phenanthridyl group; thienyl group; indolo[2,3-a]carbazolyl group; indolo[2,3-b]carbazolyl group; indolinyl group; 10,11-dihydro-dibenzo[b,f]azepinyl group; 9,10-dihydroacridinyl group; phenanthrazinyl group; phenothiazinyl group; Examples thereof include, but are not limited to, a phthalazinyl group; a naphthyridinyl group; a phenanthrolinyl group; a benzo[c][1,2,5]thiadiazolyl group; a 5,10-dihydrodibenzo[b,e][1,4]azacylinyl group; a pyrazolo[1,5-c]quinazolinyl group; a pyrido[1,2-b]indazolyl group; a pyrido[1,2-a]imidazo[1,2-e]indolinyl group; and a 5,11-dihydroindeno[1,2-b]carbazolyl group.

[0074] In the present specification, the amine group may be selected from the group consisting of a monoalkylamine group; a monoarylamine group; a monoheteroarylamine group; -NH2; a dialkylamine group; a diarylamine group; a diheteroarylamine group; an alkylarylamine group; an alkylheteroarylamine group; and an arylheteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group; a dimethylamine group; an ethylamine group; a diethylamine group; a phenylamine group; a naphthylamine group; a biphenylamine group; a dibiphenylamine group; anthracenylamine group; a 9-methyl-anthracenylamine group; a diphenylamine group; a phenylnaphthylamine group; a ditolylamine group; a phenyltolylamine group; a triphenylamine group; a biphenylnaphthylamine group; a phenylbiphenylamine group; a biphenylfluorenylamine group; a phenyltriphenylenylamine group; Biphenyltriphenylenylamine groups, etc. are included, but are not limited thereto.

[0075] 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.

[0076] As used herein, the term "adjacent" may refer to a substituent substituted on an atom directly connected to the atom substituted by the substituent; a substituent that is sterically closest to the substituent; or another substituent substituted on the atom substituted by the substituent. For example, two substituents substituted at ortho positions in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring may be interpreted as "adjacent" to each other.

[0077] In the present invention, "when no substituent is indicated in the chemical formula or compound structure" means that a hydrogen atom is bonded to a carbon atom. However, deuterium ( 2Since H, Deuterium (D)) is an isotope of hydrogen, some hydrogen atoms may be deuterium.

[0078] 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%.

[0079] 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.”

[0080] In one embodiment of the present invention, deuterium is an element having a deuteron, which is one of the isotopes of hydrogen and is composed of one proton and one neutron, as its nucleus. -2 It can be expressed as , and the element symbol is D or 2 It can also be written as H.

[0081] In one embodiment of the present invention, an isotope means an atom having the same atomic number (Z) but a different mass number (A). An isotope can also be interpreted as an element having the same number of protons but a different number of neutrons.

[0082] In one embodiment of the present invention, the meaning of the content T% of a specific substituent can be defined as T2 / T1Х100 = T%, where the total number of substituents that the basic compound can have is defined as T1, and the number of specific substituents among them is defined as T2.

[0083] 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.

[0084]

[0085] Additionally, in one embodiment of the present invention, the term “phenyl group having a deuterium content of 0%” may mean a phenyl group that does not contain deuterium atoms, i.e., has 5 hydrogen atoms.

[0086] In the present invention, the C6 to C60 aromatic hydrocarbon ring means a compound including an aromatic ring composed of C6 to C60 carbons and hydrogen, and examples thereof include, but are not limited to, a phenyl group; a biphenyl group; a terphenyl group; a triphenylenyl group; a naphthyl group; anthracenyl group; a phenalenyl group; a phenanthrenyl group; a fluorenyl group; a pyrenyl group; a chrysenyl group; a perylenyl group; an azulenyl group, and the like. All aromatic hydrocarbon ring compounds known in the art that satisfy the above carbon number are included.

[0087]

[0088] The present invention provides a heterocyclic compound represented by the following chemical formula 1.

[0089] [Chemical Formula 1]

[0090]

[0091] In the above chemical formula 1,

[0092] The above X1 and X2 are different from each other and are each independently a direct bond; NAr1; or CRaRb,

[0093] Either of the above X1 and X2 is a direct bond,

[0094] The above R1 to R4, Ra and Rb are the same as or different from each other, and each independently hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R101R102; -SiR101R102R103; And -NR101R102, or two or more adjacent groups are combined to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same as or different from each other and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0095] The above a is an integer from 0 to 6, and when a is 2 or more, R1 is equal to or different from each other,

[0096] The above b is an integer from 0 to 3, and when b is 2 or greater, R3 are equal to or different from each other,

[0097] The above Ar1 is a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0098] The above L1 is a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group,

[0099] The above c is an integer from 0 to 5, and when c is 2 or greater, L1 are equal to or different from each other,

[0100] The above N-Het is a substituted or unsubstituted C2 to C60 monocyclic or polycyclic heterocyclic group containing two or more N.

[0101]

[0102] In one embodiment of the present invention, X1 may be NAr1, and X2 may be a direct bond.

[0103] In another embodiment of the present invention, X1 may be CRaRb, and X2 may be a direct bond.

[0104] In another embodiment of the present invention, X1 may be a direct bond, and X2 may be NAr1.

[0105] In another embodiment of the present invention, X1 may be a direct bond and X2 may be CRaRb.

[0106]

[0107] In one embodiment of the present invention, R1 to R4, Ra and Rb are the same as or different from each other, and each independently hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C2 to C30 alkenyl group; a substituted or unsubstituted C2 to C30 alkynyl group; a substituted or unsubstituted C1 to C30 alkoxy group; a substituted or unsubstituted C3 to C30 cycloalkyl group; a substituted or unsubstituted C2 to C30 heterocycloalkyl group; a substituted or unsubstituted C6 to C30 aryl group; a substituted or unsubstituted C2 to C30 heteroaryl group; -P(=O)R101R102; -SiR101R102R103; Or -NR101R102, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C30 heterocycle, wherein R101, R102 and R103 are the same as or different from each other, and each independently may be a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0108] In another embodiment of the present invention, R1 to R4, Ra and Rb are the same as or different from each other, and each independently hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C2 to C20 alkenyl group; a substituted or unsubstituted C2 to C20 alkynyl group; a substituted or unsubstituted C1 to C20 alkoxy group; a substituted or unsubstituted C3 to C20 cycloalkyl group; a substituted or unsubstituted C2 to C20 heterocycloalkyl group; a substituted or unsubstituted C6 to C20 aryl group; a substituted or unsubstituted C2 to C20 heteroaryl group; -P(=O)R101R102; -SiR101R102R103; Or -NR101R102, or two or more adjacent groups combine with each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C20 heterocycle, wherein R101, R102 and R103 are the same as or different from each other, and each independently may be a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0109] In another embodiment of the present invention, R1 to R4, Ra and Rb may be the same as or different from each other, and may each independently be hydrogen; deuterium; halogen; a cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0110] In another embodiment of the present invention, R1 to R4, Ra and Rb may be the same as or different from each other, and may each independently be 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.

[0111] In another embodiment of the present invention, R1 to R4 may be the same as or different from each other, and may each independently be hydrogen; deuterium; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0112] In another embodiment of the present invention, R1, R2 and R4 are the same as or different from each other, and may each independently be hydrogen or deuterium.

[0113] In another embodiment of the present invention, R3 may be hydrogen; deuterium; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, and when b is 2 or more, R3 may be the same as or different from each other.

[0114] In another embodiment of the present invention, R3 may be hydrogen; deuterium; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group, and when b is 2 or more, R3 may be the same as or different from each other.

[0115] In another embodiment of the present invention, R3 may be hydrogen; deuterium; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group, and when b is 2 or more, R3 may be the same as or different from each other.

[0116] In another embodiment of the present invention, R3 may be hydrogen; deuterium; or a substituted or unsubstituted C6 to C20 aryl group, and when b is 2 or more, R3 are the same as or different from each other.

[0117] In another embodiment of the present invention, R3 may be hydrogen; deuterium; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted naphthyl group, and when b is 2 or more, they are the same or different.

[0118] In another embodiment of the present invention, Ra and Rb may be the same as or different from each other, and may each independently be hydrogen; deuterium; or a substituted or unsubstituted C1 to C60 alkyl group.

[0119] In another embodiment of the present invention, Ra and Rb may be the same as or different from each other, and may each independently be hydrogen; deuterium; or a substituted or unsubstituted C1 to C30 alkyl group.

[0120] In another embodiment of the present invention, Ra and Rb may be the same as or different from each other, and may each independently be hydrogen; deuterium; or a substituted or unsubstituted C1 to C20 alkyl group.

[0121] In another embodiment of the present invention, Ra and Rb may be the same as or different from each other, and may each independently be a substituted or unsubstituted C1 to C20 alkyl group.

[0122] In another embodiment of the present invention, Ra and Rb may be substituted or unsubstituted methyl groups.

[0123]

[0124] In one embodiment of the present invention, Ar1 may be a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0125] In another embodiment of the present invention, Ar1 may be a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0126] In another embodiment of the present invention, Ar1 may be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted dibenzofuranyl group.

[0127]

[0128] In one embodiment of the present invention, L1 may be a direct bond; a substituted or unsubstituted C6 to C30 arylene group; or a substituted or unsubstituted C2 to C30 heteroarylene group.

[0129] In another embodiment of the present invention, L1 may be a direct bond; a substituted or unsubstituted C6 to C20 arylene group; or a substituted or unsubstituted C2 to C20 heteroarylene group.

[0130] In another embodiment of the present invention, L1 may be a direct bond; or a substituted or unsubstituted C6 to C20 arylene group.

[0131] In another embodiment of the present invention, L1 may be a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted naphthylene group.

[0132]

[0133] In one embodiment of the present invention, the N-Het may be a substituted or unsubstituted C2 to C30 monocyclic or polycyclic heterocyclic group containing two or more Ns.

[0134] In another embodiment of the present invention, the N-Het may be a substituted or unsubstituted C2 to C20 monocyclic or polycyclic heterocyclic group containing two or more N.

[0135]

[0136] In one embodiment of the present invention, the heterocyclic compound represented by the chemical formula 1 may be represented by the following chemical formula 1-1 or chemical formula 1-2.

[0137] [Chemical Formula 1-1]

[0138]

[0139] [Chemical Formula 1-2]

[0140]

[0141] In the above chemical formulas 1-1 and 1-2,

[0142] The above X1, X2, R1 to R4, L1, a to c and N-Het are the same as defined in the above chemical formula 1.

[0143]

[0144] In one embodiment of the present invention, the heterocyclic compound represented by the chemical formula 1-1 may be represented by the following chemical formula 1-1-1, and the heterocyclic compound represented by the chemical formula 1-2 may be represented by the following chemical formula 1-2-1.

[0145] [Chemical Formula 1-1-1]

[0146]

[0147] [Chemical Formula 1-2-1]

[0148]

[0149] In the above chemical formulas 1-1-1 and 1-2-1,

[0150] The above R11 to R13 are the same as or different from each other, and each independently represent hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R101R102; -SiR101R102R103; And -NR101R102, or two or more adjacent groups are combined to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same as or different from each other and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0151] The above X1, X2, R1, R2, R4, L1, N-Het, a and c are the same as defined in the above chemical formula 1.

[0152]

[0153] In one embodiment of the present invention, R11 to R13 are the same as or different from each other, and each independently hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C2 to C30 alkenyl group; a substituted or unsubstituted C2 to C30 alkynyl group; a substituted or unsubstituted C1 to C30 alkoxy group; a substituted or unsubstituted C3 to C30 cycloalkyl group; a substituted or unsubstituted C2 to C30 heterocycloalkyl group; a substituted or unsubstituted C6 to C30 aryl group; a substituted or unsubstituted C2 to C30 heteroaryl group; -P(=O)R101R102; -SiR101R102R103; Or -NR101R102, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C30 heterocycle, wherein R101, R102 and R103 are the same as or different from each other, and each independently may be a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0154] In another embodiment of the present invention, R11 to R13 are the same as or different from each other, and each independently hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C2 to C20 alkenyl group; a substituted or unsubstituted C2 to C20 alkynyl group; a substituted or unsubstituted C1 to C20 alkoxy group; a substituted or unsubstituted C3 to C20 cycloalkyl group; a substituted or unsubstituted C2 to C20 heterocycloalkyl group; a substituted or unsubstituted C6 to C20 aryl group; a substituted or unsubstituted C2 to C20 heteroaryl group; -P(=O)R101R102; -SiR101R102R103; Or -NR101R102, or two or more adjacent groups combine with each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C20 heterocycle, wherein R101, R102 and R103 are the same as or different from each other, and each independently may be a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0155] In another embodiment of the present invention, R11 to R13 may be the same as or different from each other, and may each independently be hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0156] In another embodiment of the present invention, R11 to R13 may be the same as or different from each other, and may each independently be hydrogen; deuterium; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0157] In another embodiment of the present invention, R11 and R12 may be the same as or different from each other, and may each independently be hydrogen; deuterium; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0158] In another embodiment of the present invention, R11 and R12 may be the same as or different from each other, and may each independently be hydrogen; deuterium; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0159] In another embodiment of the present invention, R11 and R12 may be the same as or different from each other, and may each independently be hydrogen; deuterium; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0160] In another embodiment of the present invention, R11 and R12 may be the same as or different from each other, and may each independently be hydrogen; deuterium; or a substituted or unsubstituted C6 to C20 aryl group.

[0161] In another embodiment of the present invention, R11 and R12 may be the same as or different from each other, and may each independently be hydrogen; deuterium; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted naphthyl group.

[0162] In another embodiment of the present invention, R13 may be hydrogen or deuterium.

[0163]

[0164] In one embodiment of the present invention, the heterocyclic compound represented by the chemical formula 1-1 may be represented by any one of the following chemical formulas 1-1a to 1-1c.

[0165] [Chemical Formula 1-1a]

[0166]

[0167] [Chemical Formula 1-1b]

[0168]

[0169] [Chemical Formula 1-1c]

[0170]

[0171] In the above chemical formulas 1-1a to 1-1c,

[0172] The above X1, R1 to R4, L1, a to c and N-Het are the same as defined in the above chemical formula 1.

[0173]

[0174] In one embodiment of the present invention, the heterocyclic compound represented by the chemical formula 1-1a may be represented by the following chemical formula 1-1a-1, the heterocyclic compound represented by the chemical formula 1-1b may be represented by the following chemical formula 1-1b-1, and the heterocyclic compound represented by the chemical formula 1-1c may be represented by the following chemical formula 1-1c-1.

[0175] [Chemical Formula 1-1a-1]

[0176]

[0177] [Chemical Formula 1-1b-1]

[0178]

[0179] [Chemical Formula 1-1c-1]

[0180]

[0181] In the above chemical formulas 1-1a-1 to 1-1c-1,

[0182] The above X1, R1, R2, R4, L1, N-Het, a and c are the same as defined in the above chemical formula 1,

[0183] The above R11 to R13 are the same as the definitions in the above chemical formula 1-1-1.

[0184]

[0185] In one embodiment of the present invention, the heterocyclic compound represented by the chemical formula 1-2 may be represented by any one of the following chemical formulas 1-2a to 1-2c.

[0186] [Chemical Formula 1-2a]

[0187]

[0188] [Chemical Formula 1-2b]

[0189]

[0190] [Chemical Formula 1-2c]

[0191]

[0192] In the above chemical formulas 1-2a to 1-2c,

[0193] The above X2, R1 to R4, L1, a to c and N-Het are the same as defined in the above chemical formula 1.

[0194]

[0195] In one embodiment of the present invention, the heterocyclic compound represented by the chemical formula 1-2a may be represented by the following chemical formula 1-2a-1, the heterocyclic compound represented by the chemical formula 1-2b may be represented by the following chemical formula 1-2b-1, and the heterocyclic compound represented by the chemical formula 1-2c may be represented by the following chemical formula 1-2c-1.

[0196] [Chemical Formula 1-2a-1]

[0197]

[0198] [Chemical Formula 1-2b-1]

[0199]

[0200] [Chemical formula 1-2c-1]

[0201]

[0202] In the above chemical formulas 1-2a-1 to 1-2c-1,

[0203] The above X2, R1, R2, R4, L1, N-Het, a and c are the same as defined in the above chemical formula 1,

[0204] The above R11 to R13 are the same as the definitions in the above chemical formula 1-2-1.

[0205]

[0206] In one embodiment of the present invention, the N-Het may be represented by the following chemical formula 2.

[0207] [Chemical Formula 2]

[0208]

[0209] In the above chemical formula 2,

[0210] The above Y1 is N; or CRc,

[0211] The above Y2 is N; or CRd,

[0212] The above Y3 is N; or CRe,

[0213] The above Y4 is N; or CRf,

[0214] At least two of the above Y1 to Y4 are N,

[0215] The above R21 and Rc to Rf are the same as or different from each other, and each independently hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R201R202; -SiR201R202R203; And -NR201R202, or two or more adjacent groups are combined to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C60 heterocycle, wherein R201, R202 and R203 are the same as or different from each other and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0216]

[0217] In one embodiment of the present invention, three of Y1 to Y4 may be N.

[0218] In another embodiment of the present invention, two of Y1 to Y4 may be N.

[0219] In another embodiment of the present invention, Y1, Y2 and Y4 may be N, and Y3 may be CRe.

[0220] In another embodiment of the present invention, Y1 and Y2 may be N, Y3 may be CRe, and Y4 may be CRf.

[0221] In another embodiment of the present invention, Y1 and Y4 may be N, Y2 may be CRd, and Y3 may be CRe.

[0222] In another embodiment of the present invention, Y1 and Y3 may be N, Y2 may be CRd, and Y4 may be CRf.

[0223]

[0224] In one embodiment of the present invention, R21 and Rc to Rf are the same as or different from each other, and each independently hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C2 to C30 alkenyl group; a substituted or unsubstituted C2 to C30 alkynyl group; a substituted or unsubstituted C1 to C30 alkoxy group; a substituted or unsubstituted C3 to C30 cycloalkyl group; a substituted or unsubstituted C2 to C30 heterocycloalkyl group; a substituted or unsubstituted C6 to C30 aryl group; a substituted or unsubstituted C2 to C30 heteroaryl group; -P(=O)R201R202; -SiR201R102R103; Or -NR201R202, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C30 heterocycle, wherein R201, R202 and R203 are the same as or different from each other, and each independently may be a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0225] In another embodiment of the present invention, R21 and Rc to Rf are the same as or different from each other, and each independently hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C2 to C20 alkenyl group; a substituted or unsubstituted C2 to C20 alkynyl group; a substituted or unsubstituted C1 to C20 alkoxy group; a substituted or unsubstituted C3 to C20 cycloalkyl group; a substituted or unsubstituted C2 to C20 heterocycloalkyl group; a substituted or unsubstituted C6 to C20 aryl group; a substituted or unsubstituted C2 to C20 heteroaryl group; -P(=O)R201R202; -SiR201R102R103; Or -NR201R202, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C20 heterocycle, wherein R201, R202 and R203 are the same as or different from each other, and each independently may be a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0226] In another embodiment of the present invention, R21 and Rc to Rf are the same as or different from each other, and each independently represent hydrogen; deuterium; halogen; a cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group, or two or more adjacent groups may combine with each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C20 heterocycle.

[0227]

[0228] In one embodiment of the present invention, the chemical formula 2 may be represented by any one of the following chemical formulas 2-1 to 2-7.

[0229] [Chemical Formula 2-1]

[0230]

[0231] [Chemical Formula 2-2]

[0232]

[0233] [Chemical Formula 2-3]

[0234]

[0235] [Chemical Formula 2-4]

[0236]

[0237] [Chemical Formula 2-5]

[0238]

[0239] [Chemical Formula 2-6]

[0240]

[0241] [Chemical Formula 2-7]

[0242]

[0243] In the above chemical formulas 2-1 to 2-7,

[0244] The above Y11 is O; or S,

[0245] The above R22 to R26 are the same as or different from each other, and each independently represent hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R201R202; -SiR201R202R203; And -NR201R202, wherein R201, R202 and R203 are the same as or different from each other, and each independently represents a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0246] The above f is an integer from 0 to 4, and when f is 2 or greater, R26 are equal to or different from each other,

[0247] The above L11 and L12 are the same as or different from each other, and each independently represents a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group,

[0248] The above d is an integer from 0 to 5, and when d is 2 or greater, L11 are equal to or different from each other,

[0249] The above e is an integer from 0 to 5, and when e is 2 or greater, L12 are equal to or different from each other,

[0250] The above Ar11 to Ar13 are the same as or different from each other, and each independently represents a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0251]

[0252] In one embodiment of the present invention, Y may be O.

[0253] In another embodiment of the present invention, Y may be S.

[0254]

[0255] In one embodiment of the present invention, R22 to R26 are the same as or different from each other, and each independently hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C2 to C30 alkenyl group; a substituted or unsubstituted C2 to C30 alkynyl group; a substituted or unsubstituted C1 to C30 alkoxy group; a substituted or unsubstituted C3 to C30 cycloalkyl group; a substituted or unsubstituted C2 to C30 heterocycloalkyl group; a substituted or unsubstituted C6 to C30 aryl group; a substituted or unsubstituted C2 to C30 heteroaryl group; -P(=O)R201R202; -SiR201R102R103; Or -NR201R202, wherein R201, R202 and R203 are the same as or different from each other, and each independently may be a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0256] In another embodiment of the present invention, R22 to R26 are the same as or different from each other, and each independently hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C2 to C20 alkenyl group; a substituted or unsubstituted C2 to C20 alkynyl group; a substituted or unsubstituted C1 to C20 alkoxy group; a substituted or unsubstituted C3 to C20 cycloalkyl group; a substituted or unsubstituted C2 to C20 heterocycloalkyl group; a substituted or unsubstituted C6 to C20 aryl group; a substituted or unsubstituted C2 to C20 heteroaryl group; -P(=O)R201R202; -SiR201R102R103; Or -NR201R202, wherein R201, R202 and R203 are the same as or different from each other, and each independently may be a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0257] In another embodiment of the present invention, R22 to R26 may be the same as or different from each other, and may each independently be hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0258] In another embodiment of the present invention, R22 and R23 may be the same as or different from each other, and may each independently be a halogen; a cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0259] In another embodiment of the present invention, R22 and R23 may be the same as or different from each other, and each independently be halogen; a cyano group; a substituted or unsubstituted tert-butyl 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 phenanthrenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted dibenzothiophenyl group; or a substituted or unsubstituted carbazolyl group.

[0260] In another embodiment of the present invention, R24 to R26 are the same as or different from each other, and may each independently be hydrogen or deuterium.

[0261]

[0262] In one embodiment of the present invention, Ar11 to Ar13 may be the same as or different from each other, and may each independently be a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0263] In another embodiment of the present invention, Ar11 to Ar13 may be the same as or different from each other, and may each independently be a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0264] In another embodiment of the present invention, Ar11 to Ar13 may be the same as or different from each other, and may each independently be a substituted or unsubstituted C6 to C20 aryl group.

[0265] In another embodiment of the present invention, Ar11 to Ar13 may be the same as or different from each other, and may each independently be a substituted or unsubstituted phenyl group.

[0266]

[0267] In one embodiment of the present invention, L11 and L12 may be the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted C6 to C30 arylene group; or a substituted or unsubstituted C2 to C30 heteroarylene group.

[0268] In another embodiment of the present invention, L11 and L12 may be the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted C6 to C20 arylene group; or a substituted or unsubstituted C2 to C20 heteroarylene group.

[0269] In another embodiment of the present invention, L11 and L12 may be the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted naphthylene group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted carbazolene group.

[0270]

[0271] In one embodiment of the present invention, all of R1 to R4, R11 to R13, R21 to R26, Ra to Rf, L1, L11, L12, Ar1 and Ar11 to Ar13 may include non-deuterated hydrogen (H).

[0272] In another embodiment of the present invention, at least one of R1 to R4, R11 to R13, R21 to R26, Ra to Rf, L1, L11, L12, Ar1 and Ar11 to Ar13 contains deuterium (D), and at least one of R1 to R4, R11 to R13, R21 to R26, Ra to Rf, L1, L11, L12, Ar1 and Ar11 to Ar13 may contain non-deuterated hydrogen.

[0273] In another embodiment of the present invention, R1 to R4, R11 to R13, R21 to R26, Ra to Rf, L1, L11, L12, Ar1 and Ar11 to Ar13 may all contain deuterium.

[0274]

[0275] In one embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 1 may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be, for example, more than 0%, 1% or more, 10% or more, 20% or more, 30% or more, 40% or more, or 50% or more, and may be 100% or less, 90% or less, 80% or less, 70% or less, or 60% or less.

[0276] In another embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 1 may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 1% to 100%.

[0277] In another embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 1 may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 20% to 90%.

[0278] In another embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 1 may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 30% to 80%.

[0279] In another embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 1 may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 50% to 70%.

[0280]

[0281] In one embodiment of the present invention, the heterocyclic compound represented by the chemical formula 1 may be represented by any one of the following compounds.

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299]

[0300]

[0301]

[0302]

[0303]

[0304] In addition, by introducing various substituents into the structure of the heterocyclic compound represented by the above chemical formula 1, it is possible to synthesize a compound having the unique characteristics of the introduced substituent. For example, by introducing a substituent mainly used in hole injection layer materials, hole transport layer materials, light-emitting layer materials, electron transport layer materials, electron blocking layer materials, and charge generation layer materials used in the manufacture of organic light-emitting devices into the core structure, it is possible to synthesize a material that satisfies the conditions required for each organic layer.

[0305] In addition, by introducing various substituents into the structure of the heterocyclic compound represented by 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.

[0306] Meanwhile, the heterocyclic compound represented by the above chemical formula 1 has a high glass transition temperature (Tg) and thus excellent thermal stability. This increase in thermal stability is an important factor in providing operating stability to the device.

[0307] The heterocyclic compound according to one embodiment of the present invention can be prepared through a multi-step chemical reaction. Some intermediate compounds are prepared first, and then the heterocyclic compound represented by Chemical Formula 1 can be prepared from these intermediate compounds. More specifically, the heterocyclic compound according to one embodiment of the present invention can be prepared based on the preparation example described below.

[0308]

[0309] 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”.

[0310]

[0311] In addition, the present invention

[0312] First electrode;

[0313] A second electrode provided opposite to the first electrode; and

[0314] An organic light-emitting device comprising at least one organic layer provided between the first electrode and the second electrode,

[0315] The present invention relates to an organic light-emitting device, wherein at least one of the organic layers comprises a heterocyclic compound represented by the chemical formula 1.

[0316]

[0317] In one embodiment of the present invention, the first electrode may be an anode, and the second electrode may be a cathode.

[0318] In another embodiment, the first electrode may be a cathode and the second electrode may be an anode.

[0319]

[0320] In one embodiment of the present invention, the organic light-emitting device may be a red organic light-emitting device, and the heterocyclic compound represented by the chemical formula 1 may be used as a material for the red organic light-emitting material.

[0321] In another embodiment of the present invention, the organic light-emitting device may be a blue organic light-emitting device, and the heterocyclic compound represented by the chemical formula 1 may be used as a material for the blue organic light-emitting material.

[0322] In another embodiment of the present invention, the organic light-emitting device may be a green organic light-emitting device, and the heterocyclic compound represented by the chemical formula 1 may be used as a material for the green organic light-emitting material.

[0323]

[0324] In one embodiment of the present invention, the organic light-emitting device may be a red organic light-emitting device, and the heterocyclic compound represented by the chemical formula 1 may be used as a light-emitting layer material of the red organic light-emitting device.

[0325] In another embodiment of the present invention, the organic light-emitting device may be a blue organic light-emitting device, and the heterocyclic compound represented by the chemical formula 1 may be used as a light-emitting layer material of the blue organic light-emitting device.

[0326] In another embodiment of the present invention, the organic light-emitting device may be a green organic light-emitting device, and the heterocyclic compound represented by the chemical formula 1 may be used as a light-emitting layer material of the green organic light-emitting device.

[0327]

[0328] The specific details of the heterocyclic compound represented by the above chemical formula 1 are the same as described above.

[0329]

[0330] The organic light-emitting device of the present invention can be manufactured using a conventional method and material for manufacturing an organic light-emitting device, except that one or more organic layers are formed using the above-described heterocyclic compound.

[0331] 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.

[0332] The organic layer of the organic light-emitting device of the present invention may be formed as a single layer structure, but may also be formed as a multilayer structure in which two or more organic layers are laminated. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, an electron blocking layer, a hole transport layer, a light-emitting layer, an electron transport layer, a hole blocking layer, an electron injection layer, etc. as the organic layers. However, the structure of the organic light-emitting device is not limited thereto and may include a smaller number of organic layers.

[0333]

[0334] In the organic light-emitting device of the present invention, the organic layer includes a light-emitting layer, and the light-emitting layer may include a heterocyclic compound represented by the chemical formula 1. When the heterocyclic compound is used in the light-emitting layer, the HOMO (Highest Occupied Molecular Orbital) and the LUMO (Lowest Unoccupied Molecular Orbital) are spatially separated, thereby enabling strong charge transfer, and thus the operating efficiency and lifespan of the organic light-emitting device may be improved.

[0335]

[0336] In an organic light-emitting device according to one embodiment of the present invention, an organic material layer including a heterocyclic compound represented by the above chemical formula 1 further includes a heterocyclic compound represented by the following chemical formula 3.

[0337] [Chemical Formula 3]

[0338]

[0339] In the above chemical formula 3,

[0340] wherein R31 and R32 are the same as or different from each other, and each independently represent hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R301R302; -SiR301R302R303; And -NR301R302, 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 R301, R302 and R303 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,

[0341] The above g is an integer from 0 to 3, and when g is 2 or greater, R31 are equal to or different from each other,

[0342] The above h is an integer from 0 to 5, and when h is 2 or greater, R32 are equal to or different from each other,

[0343] The above L31 to L34 are the same or different from each other, and each independently represents a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group,

[0344] The above i is an integer from 0 to 5, and when i is 2 or greater, L31 are equal to or different from each other,

[0345] The above j is an integer from 0 to 5, and when j is 2 or greater, L32 are equal to or different from each other,

[0346] The above k is an integer from 0 to 5, and when k is 2 or greater, L33 are equal to or different from each other,

[0347] The above l is an integer from 0 to 5, and when l is 2 or greater, L34 are equal to or different from each other,

[0348] The above Ar31 to Ar33 are the same as or different from each other, and each independently represents a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0349]

[0350] In one embodiment of the present invention, R31 and R32 are the same as or different from each other, and each independently hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C2 to C30 alkenyl group; a substituted or unsubstituted C2 to C30 alkynyl group; a substituted or unsubstituted C1 to C30 alkoxy group; a substituted or unsubstituted C3 to C30 cycloalkyl group; a substituted or unsubstituted C2 to C30 heterocycloalkyl group; a substituted or unsubstituted C6 to C30 aryl group; a substituted or unsubstituted C2 to C30 heteroaryl group; -P(=O)R301R302; -SiR301R302R303; Or -NR301R302, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C30 heterocycle, wherein R301, R302 and R303 are the same as or different from each other, and each independently may be a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0351] In one embodiment of the present invention, R31 and R32 are the same as or different from each other, and each independently hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C2 to C20 alkenyl group; a substituted or unsubstituted C2 to C20 alkynyl group; a substituted or unsubstituted C1 to C20 alkoxy group; a substituted or unsubstituted C3 to C20 cycloalkyl group; a substituted or unsubstituted C2 to C20 heterocycloalkyl group; a substituted or unsubstituted C6 to C20 aryl group; a substituted or unsubstituted C2 to C20 heteroaryl group; -P(=O)R301R302; -SiR301R302R303; Or -NR301R302, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C20 heterocycle, wherein R301, R302 and R303 are the same as or different from each other, and each independently may be a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0352] In one embodiment of the present invention, R31 and R32 may be the same as or different from each other, and each independently be hydrogen; deuterium; halogen; a cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C2 to C20 alkenyl group; a substituted or unsubstituted C2 to C20 alkynyl group; a substituted or unsubstituted C1 to C20 alkoxy group; a substituted or unsubstituted C3 to C20 cycloalkyl group; a substituted or unsubstituted C2 to C20 heterocycloalkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0353] In one embodiment of the present invention, R31 and R32 may be the same as or different from each other, and each independently be hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0354] In one embodiment of the present invention, R31 and R32 are the same as or different from each other, and may each independently be hydrogen or deuterium.

[0355]

[0356] In one embodiment of the present invention, L31 to L34 may be the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted C6 to C30 arylene group; or a substituted or unsubstituted C2 to C30 heteroarylene group.

[0357] In another embodiment of the present invention, L31 to L34 may be the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted C6 to C20 arylene group; or a substituted or unsubstituted C2 to C20 heteroarylene group.

[0358] In another embodiment of the present invention, L31 may be a direct bond; a substituted or unsubstituted C6 to C20 arylene group.

[0359] In another embodiment of the present invention, L31 may be a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted naphthylene group.

[0360] In another embodiment of the present invention, L32 and L33 may be the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted dibenzofuralene group; or a substituted or unsubstituted carbazolene group.

[0361] In another embodiment of the present invention, L34 may be a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted carbazolene group.

[0362]

[0363] In one embodiment of the present invention, Ar31 to Ar33 may be the same as or different from each other, and may each independently be a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0364] In another embodiment of the present invention, Ar31 to Ar33 may be the same as or different from each other, and may each independently be a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0365] In another embodiment of the present invention, Ar31 and Ar32 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 phenanthrenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted carbazolyl group; or a substituted or unsubstituted dibenzothiophenyl group.

[0366] In another embodiment of the present invention, Ar33 may be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted carbazolyl group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group.

[0367]

[0368] In one embodiment of the present invention, the heterocyclic compound represented by the chemical formula 3 may be represented by the following chemical formula 3-1 or chemical formula 3-2.

[0369] [Chemical Formula 3-1]

[0370]

[0371] [Chemical Formula 3-2]

[0372]

[0373] In the above chemical formulas 3-1 and 3-2,

[0374] The above R31, R32, L31 to L34, Ar31 to Ar33 and g to l are the same as defined in the above chemical formula 3.

[0375]

[0376] In one embodiment of the present invention, R31, R32, L31 to L34 and Ar31 to Ar33 may all include non-deuterated hydrogen (H).

[0377] In another embodiment of the present invention, at least one of R31, R32, L31 to L34 and Ar31 to Ar33 may contain deuterium (D), and at least one of R31, R32, L31 to L34 and Ar31 to Ar33 may contain non-deuterated hydrogen.

[0378] In another embodiment of the present invention, R31, R32, L31 to L34 and Ar31 to Ar33 may all contain deuterium.

[0379]

[0380] In one embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 3 may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be, for example, more than 0%, 1% or more, 10% or more, 20% or more, 30% or more, 40% or more, or 50% or more, and may be 100% or less, 90% or less, 80% or less, 70% or less, or 60% or less.

[0381] In another embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 3 may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 1% to 100%.

[0382] In another embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 3 may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 20% to 90%.

[0383] In another embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 3 may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 30% to 80%.

[0384] In another embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 3 may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 50% to 70%.

[0385]

[0386] When the heterocyclic compound represented by the above chemical formula 1 and the heterocyclic compound represented by the above chemical formula 3 are simultaneously included, superior efficiency and lifespan effects are exhibited. From this, it can be expected that an exciplex phenomenon will occur when the two compounds are simultaneously included.

[0387] The above exciplex phenomenon is a phenomenon in which energy of the size of the HOMO energy level of the donor (p-host) and the LUMO energy level of the acceptor (n-host) is released due to electron exchange between two molecules. When the exciplex phenomenon between two molecules occurs, reverse intersystem crossing (RISC) occurs, and this can increase the internal quantum efficiency of fluorescence up to 100%. When a donor (p-host) with a good hole transport ability and an acceptor (n-host) with a good electron transport ability are used as hosts of the light-emitting layer, holes are injected into the p-host and electrons are injected into the n-host, so the driving voltage can be lowered, which can help improve the lifespan. That is, when the compound represented by the above chemical formula 3 is used as the donor and the compound represented by the above chemical formula 1 is used as the acceptor, excellent device characteristics are exhibited.

[0388]

[0389] In one embodiment of the present invention, when the heterocyclic compound represented by the above chemical formula 1 and the heterocyclic compound represented by the above chemical formula 3 are simultaneously included, at least one of the compounds may not include deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be more than 0%, 1% or more, 10% or more, 20% or more, 30% or more, 40% or more, or 50% or more, and may be 100% or less, 90% or less, 80% or less, 70% or less, or 60% or less.

[0390] In another embodiment of the present invention, at least one of the compounds may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 1% to 100%.

[0391] In another embodiment of the present invention, at least one of the compounds may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 20% to 90%.

[0392] In another embodiment of the present invention, at least one of the compounds may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 30% to 80%.

[0393] In another embodiment of the present invention, at least one of the compounds may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 50% to 70%.

[0394]

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

[0396]

[0397]

[0398]

[0399]

[0400]

[0401]

[0402]

[0403]

[0404]

[0405]

[0406]

[0407]

[0408]

[0409] In addition, one embodiment of the present invention provides a composition for an organic layer comprising a heterocyclic compound represented by the above chemical formula 1 and a heterocyclic compound represented by the above chemical formula 3.

[0410] The specific details of the heterocyclic compound represented by the above chemical formula 1 and the heterocyclic compound represented by the above chemical formula 3 are the same as described above.

[0411]

[0412] In one embodiment of the present invention, the weight ratio of the heterocyclic compound represented by the chemical formula 1 and the heterocyclic compound represented by the chemical formula 3 in the composition for the organic layer may be 1:9 to 9:1, 2:8 to 8:2, 1:9 to 5:5, or 2:8 to 5:5, but is not limited thereto.

[0413]

[0414] The above composition for an organic layer can be used when forming an organic material of an organic light-emitting device, and in particular, can be more preferably used when forming a host for a light-emitting layer.

[0415]

[0416] In one embodiment of the present invention, the organic layer includes a heterocyclic compound represented by the chemical formula 1 and a heterocyclic compound represented by the chemical formula 3, and can be used together with a phosphorescent dopant.

[0417] As the above phosphorescent dopant material, those known in the art can be used. For example, phosphorescent dopant materials represented by LL'MX', LL'L"M, LMX'X", L2MX', and L3M can be used, but the scope of the present invention is not limited by these examples.

[0418] The above M can be iridium, platinum, osmium, etc.

[0419] The above L is sp 2 An anionic two-dentate ligand coordinated to M by carbon and heteroatoms, and X can perform the function of trapping electrons or holes. Non-limiting examples of L include 2-(1-naphthyl)benzoxazole, 2-phenylbenzoxazole, 2-phenylbenzothiazole, 7,8-benzoquinoline, phenylpyridine, benzothiophenylpyridine, 3-methoxy-2-phenylpyridine, thiophenylpyridine, tolylpyridine, etc. Non-limiting examples of X' and X" include acetylacetonate (acac), hexafluoroacetylacetonate, salicylidene, picolinate, 8-hydroxyquinolinate, etc.

[0420] Specific examples of the above phosphorescent dopants are shown below, but are not limited to these examples.

[0421]

[0422]

[0423] In one embodiment of the present invention, the organic layer includes a heterocyclic compound represented by the chemical formula 1 and a heterocyclic compound represented by the chemical formula 3, and can be used together with an iridium-based dopant.

[0424]

[0425] In one embodiment of the present invention, the iridium-based dopant may be (piq)2(Ir)(acac) as a red phosphorescent dopant or Ir(ppy)3 as a green phosphorescent dopant.

[0426]

[0427] In one embodiment of the present invention, the content of the dopant may be 1% to 15%, preferably 2% to 10%, and more preferably 3% to 7% based on the total weight of the light-emitting layer.

[0428]

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

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

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

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

[0433] In an organic light-emitting device according to another embodiment, the organic layer includes a light-emitting layer, and the light-emitting layer may include a heterocyclic compound represented by the chemical formula 1 and a heterocyclic compound represented by the chemical formula 3.

[0434] In an organic light-emitting device according to another embodiment, the organic layer includes a light-emitting layer, the light-emitting layer includes a host material, and the host material may include a heterocyclic compound represented by the chemical formula 1.

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

[0436] In an organic light-emitting device according to another embodiment, the light-emitting layer may be used by pre-mixing two or more host materials, and at least one of the two or more host materials may include a heterocyclic compound represented by the chemical formula 1, and the other may include a heterocyclic compound represented by the chemical formula 3.

[0437] The above pre-mixed means that the light-emitting layer is mixed by first mixing the materials and storing them in one supply source before depositing two or more host materials on the organic layer.

[0438]

[0439] An organic light-emitting device according to one embodiment of the present invention may further include one or two or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

[0440]

[0441] The stacking order of electrodes and organic layers of an organic light-emitting device according to one embodiment of the present invention is illustrated in FIGS. 1 to 3. However, the scope of the present application is not intended to be limited by these drawings, and the structure of an organic light-emitting device known in the art may also be applied to the present application.

[0442] 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.

[0443] 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.

[0444]

[0445] In one embodiment of the present invention,

[0446] Steps to prepare the substrate;

[0447] A step of forming a first electrode on the substrate;

[0448] A step of forming one or more organic layers on the first electrode; and

[0449] A method for manufacturing an organic light-emitting device, comprising: forming a second electrode on the organic layer of one or more layers; wherein the step of forming the organic layer of one or more layers includes forming the organic layer of one or more layers using a composition for an organic layer according to one embodiment of the present invention.

[0450]

[0451] In one embodiment of the present invention, the step of forming the organic layer may be to pre-mix the heterocyclic compound represented by the chemical formula 1 and the heterocyclic compound represented by the chemical formula 3, and form the organic layer using a thermal vacuum deposition method.

[0452] The above pre-mixed means that the heterocyclic compound represented by the above chemical formula 1 and the heterocyclic compound represented by the above chemical formula 3 are mixed in one supply source before being deposited on the organic layer.

[0453] The pre-mixed material may be referred to as a composition for an organic layer according to one embodiment of the present application.

[0454] The organic layer including the heterocyclic compound represented by the above chemical formula 1 may additionally include other substances as needed.

[0455] The organic layer containing both the heterocyclic compound represented by the above chemical formula 1 and the heterocyclic compound represented by the above chemical formula 2 may additionally contain other substances as needed.

[0456]

[0457] In the organic light-emitting device according to one embodiment of the present invention, materials other than the heterocyclic compound represented by the above chemical formula 1 and the heterocyclic compound represented by the above chemical formula 3 are exemplified below, but these are only for exemplification and are not intended to limit the scope of the present application, and may be replaced with materials known in the art.

[0458]

[0459] 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.

[0460]

[0461] 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.

[0462]

[0463] As the hole injection layer material, a known hole injection layer material may be used, for example, a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429, or a starburst amine derivative described in the literature [Advanced Material, 6, p. 677 (1994)], such as tris(4-carbazoyl-9-ylphenyl)amine (TCTA), 4,4',4"-tris[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB), a soluble conductive polymer such as polyaniline / dodecylbenzenesulfonic acid, or Poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate), polyaniline / camphor sulfonic acid, or polyaniline / poly(4-styrenesulfonate) can be used.

[0464]

[0465] Pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, etc. can be used as hole transport layer materials, and low molecular weight or high molecular weight materials can also be used.

[0466]

[0467] As the electron transport layer material, metal complexes of oxadiazole derivatives, anthraquinodimethane and derivatives thereof, benzoquinone and derivatives thereof, naphthoquinone and derivatives thereof, anthraquinone and derivatives thereof, tetracyanoanthraquinodimethane and derivatives thereof, fluorenone derivatives, diphenyldicyanoethylene and derivatives thereof, diphenoquinone derivatives, 8-hydroxyquinoline and derivatives thereof, etc. can be used, and not only low molecular weight substances but also high molecular weight substances can be used.

[0468]

[0469] For example, LiF is typically used as an electron injection layer material in the art, but the present application is not limited thereto.

[0470]

[0471] Red, green, or blue light-emitting materials can be used as the light-emitting layer material, and if necessary, two or more light-emitting materials can be mixed and used. At this time, two or more light-emitting materials can be deposited and used as individual sources, or can be pre-mixed and deposited and used as a single source. In addition, a fluorescent material can be used as the light-emitting layer material, but a phosphorescent material can also be used. A material that emits light by combining holes and electrons injected from the anode and cathode, respectively, can be used as the light-emitting layer material, but materials in which both the host material and the dopant material participate in light emission can also be used.

[0472]

[0473] When using a mixture of host materials for the light-emitting layer, hosts of the same series may be mixed and used, or hosts of different series may be mixed and used. For example, two or more types of materials, either n-type host materials or p-type host materials, may be selected and used as the host material for the light-emitting layer.

[0474]

[0475] An organic light-emitting device according to one embodiment of the present invention may be a front-emitting, back-emitting, or double-sided emitting device depending on the material used.

[0476]

[0477] The heterocyclic compound according to one embodiment of the present invention can function in organic electronic devices, including organic solar cells, organic photoconductors, organic transistors, etc., on a principle similar to that applied to organic light-emitting devices.

[0478]

[0479] 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.

[0480]

[0481] Manufacturing Example 1. Preparation of Compound A1

[0482]

[0483]

[0484] Manufacturing Example 1-1. Preparation of Compound A1-4

[0485] 2-Bromo-3-fluoro-5-phenyl-5H-benzo[b]carbazole (30.0 g, 76.9 mmol), (2-chloro-6-methoxyphenyl)boronic acid (15.8 g, 84.6 mmol), Pd(PPh3)4 (4.44 g, 3.84 mmol), and K2CO3 (31.9 g, 231 mmol) were added to 300 mL of 1,4-dioxane and 90 mL of distilled water (H2O), and stirred at 95°C for 2 hours.

[0486] After cooling to room temperature, the resulting solid was filtered to obtain compound A1-4 (30.6 g, 88%).

[0487]

[0488] Manufacturing Example 1-2. Preparation of Compound A1-3

[0489] Compound A1-4 (30.6 g, 67.7 mmol) was added to 300 mL of dichloromethane (DCM), and BBr3 (42.4 g, 169 mmol) was slowly added at 0°C, followed by stirring at room temperature for 2 hours.

[0490] After cooling to 0℃, distilled water was added in small amounts to neutralize. After confirming that neutralization had occurred and that an exothermic reaction had not occurred, an excess of distilled water was added to precipitate a solid, and the resulting solid was filtered to obtain compound A1-3 (28.3 g, 95%).

[0491]

[0492] Manufacturing Example 1-3. Preparation of Compound A1-2

[0493] Compound A1-3 (28.3 g, 64.6 mmol) and CS2CO3 (52.6 g, 162 mmol) were added to 300 mL of dimethylacetamide (DMA) and stirred at 180°C for 5 hours.

[0494] After cooling to room temperature, the resulting solid was filtered to obtain compound A1-2 (18.5 g, 68%).

[0495]

[0496] Manufacturing Example 1-4. Preparation of Compound A1-1

[0497] Compound A1-2 (18.5 g, 44.3 mmol), B2pin2 (22.5 g, 88.5 mmol), Pd2dba3 (2.03 g, 2.21 mmol), Xphos (2.11 g, 4.43 mmol), and KOAc (13.0 g, 133 mmol) were added to 200 mL of 1,4-Dioxane and stirred at 120°C for 2 hours.

[0498] After filtering the reaction solution at the above temperature, the filtrate was concentrated under reduced pressure and filtered through silica gel to obtain compound A1-1 (14.7 g, 67%).

[0499]

[0500] Manufacturing Example 1-5. Preparation of Compound A1

[0501] Compound A1-1 (14.7 g, 29.7 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (7.94 g, 29.7 mmol), Pd(PPh3)4 (1.71 g, 1.48 mmol), and K2CO3 (12.3 g, 89.0 mmol) were added to 150 mL of 1,4-Dioxane and 50 mL of distilled water (H2O), and stirred at 95°C for 2 hours.

[0502] After cooling to room temperature, the resulting solid was filtered to obtain compound A1 (16.3 g, 89%).

[0503]

[0504] Except that Compound A of Table 1 below was used instead of A1-5 in Manufacturing Example 1, and Compound B of Table 1 below was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, the target compound was prepared in the same manner as Manufacturing Example 1, as shown in Table 1 below.

[0505]

[0506]

[0507]

[0508]

[0509]

[0510]

[0511]

[0512]

[0513]

[0514]

[0515]

[0516]

[0517] Manufacturing Example 2. Preparation of Compound B4

[0518]

[0519] 7-Chloro-5-phenylnaphtho[1,2-b]benzofuran (10.0 g, 30.1 mmol), N-([1,1'-biphenyl]-4-yl)-[1,1':4',1''-terphenyl]-4-amine (12.2 g, 30.1 mmol), Pd2(dba)3 (1.38 g, 1.51 mmol), Xphos (1.44 g, 3.01 mmol), and NaOtBu (5.79 g, 60.2 mmol) were added to 100 mL of xylene and stirred at 150°C for 2 hours.

[0520] After cooling to room temperature, the resulting solid was filtered to obtain compound B4 (17.2 g, 83%).

[0521]

[0522] Except that Compound C of Table 2 below was used instead of B4-1 in Manufacturing Example 2, and Compound D of Table 2 below was used instead of N-([1,1'-biphenyl]-4-yl)-[1,1':4',1''-terphenyl]-4-amine, the target compound was prepared in the same manner as Manufacturing Example 2, as shown in Table 2 below.

[0523]

[0524]

[0525]

[0526] Manufacturing Example 3. Preparation of Compound B20

[0527]

[0528] 7-chloro-5-phenylnaphtho[1,2-b]benzofuran (8.00 g, 24.1 mmol), [4-[N-(3-phenylphenyl)-4-(4-phenylphenyl)anilino]phenyl]boronic acid (12.5 g, 24.1 mmol), Pd2(dba)3 (1.10 g, 1.20 mmol), Xphos (1.15 g, 2.41 mmol), and NaOH (2.89 g, 72.2 mmol) were added to 100 mL of 1,4-dioxane and 30 mL of distilled water (H2O), and stirred at 110°C for 2 hours. Stirred.

[0529] After cooling to room temperature, the resulting solid was filtered to obtain compound B20 (17.2 g, 83%).

[0530]

[0531] Except that Compound E of the following Table 3 was used instead of B20-1 in the above Manufacturing Example 3, and Compound F of the following Table 3 was used instead of [4-[N-(3-phenylphenyl)-4-(4-phenylphenyl)anilino]phenyl]boronic acid, the target compound was prepared in the same manner as Manufacturing Example 3, as shown in Table 3 below.

[0532]

[0533]

[0534]

[0535] The remaining compounds other than those described in Manufacturing Examples 1 to 3 and Tables 1 to 3 were also manufactured using the same method as described in the above Manufacturing Examples, and the synthesis results are shown in Tables 4 and 5 below. Table 4 below is 1 The values ​​are measured by H NMR (CDCl3, 300 MHz), and Table 5 below is measured by FD-mass spectrometry (FD-MS: Field desorption mass spectrometry).

[0536]

[0537] Compound number 1H NMR(CDCl3, 300MHz)A18.45-8.32 (5H, m), 7.84 (1H, ddd), 7.75 (1H, ddd), 7.63-7.49 (17H, m), 7.42-7.40 (2H, m)A38.36 (2H, ddd), 8.28-8.25 (3H, m), 7.84 (1H, ddd), 7.80-7,73 (3H, m), 7.66-7.38 (19H, m), 7.25 (2H, dd)A208.36 (2H, ddd), 8.28 (1H, ddd), 7.98 (1H, dd), 7.84 (1H, ddd), 7.76 (1H, ddd), 7.66-7.37 (21H, m), 7.31 (1H, ddd)A518.51 (1H, dd), 8.36 (4H, ddd), 8.11 (1H, ddd), 8.00 (1H, d), 7.68-7.41 (19H, m)A538.52 (1H, dd), 8.34 (2H, ddd), 8. 26 (2H, dd), 8.11 (1H, dd), 7.99 (1H, dd), 7.75-7.41 (21H, m), 7.24 (2H, dd)A558.51 (1H, dd), 8.36 (2H, ddd), 8.26-8.23 (2H, m), 8.11 (1H, dd), 8.00 (1H, d), 7.79-7.41 (23H, m)A698.52 (1H, dd), 8.38 (2H, ddd), 8.09 (1H, dd), 8.00-7.98 (2H, m), 7.67-7.40 (22H, m), 7.31(1H, ddd)A718.52 (1H, dd), 8.36 (2H, ddd), 8.11 (1H, ddd), 8.00 (1H, d), 7.82 (1H, d), 7.69-7.31 (21H, m)A788.57-8.51 (2H, m), 8.37 (2H, ddd), 8.19 (1H, dd), 8.11 (1H, ddd), 8.01 (1H, d), 7.68-7.41 (18H, m), 7.20-7.11 (4H, m)A839.08 (1H, dd), 8.51-8.48 (2H, m), 8.36 (2H, ddd), 8.15-8.11 (2H, m), 8.00-7.97 (2H, m), 7.77-7.38 (23H, m)A878.52 (1H, dd), 8.38 (4H, ddd), 8.20 (2H, dd), 8.11 (1H, dd), 8.01 (1H, d), 7.93 (2H, dd), 7.75-7.40 (19H, m)A898.51 (1H, dd), 8.36-8.31 (6H, m), 8.11 (1H, ddd), 8.00 (1H, d), 7.90 (1H, dd), 7.75-7.40 (24H, m)A948.52 (1H, dd), 8.12 (1H, ddd), 8.00 (1H, d), 7.86-7.45 (18H, m), 7.33-7.31 (2H, m)A998.53 (1H, dd), 8.35 (4H, ddd), 7.98 (1H, ddd), 7.61-7.41 (20H, m)A1038.54 (1H, dd), 8.34 (2H, ddd), 8.25-8.24 (2H, m), 7.98 (1H, ddd), 7.79 (2H, ddd), 7.63-7.39 (22H, m)A1048.54 (1H, dd), 8.36 (2H, ddd), 8.29-8.26 (4H, m), 7.99 (1H, ddd), 7.79 (2H, ddd), 7.63-7.40 (24H, m)A1158.53 (1H, dd), 8.37 (2H, ddd), 7.99-7.97 (2H, m), 7.62-7.30 (23H, m)A1208.53 (1H, dd), 8.45 (2H, dd), 8.36 (2H, ddd), 7.99-7.96 (2H, m), 7.86 (1H, dd), 7.62-7.41 (20H, m)A1358.53 (1H, dd), 8.35 (4H, ddd), 7.99-7.97 (2H, m), 7.61-7.24 (21H, m),A1378.53 (1H, dd), 8.24 (1H, s), 7.99-7.94 (5H, m), 7.62-7.41 (20H, m)A1418.35 (4H, ddd), 8.17 (1H, d), 7.97 (1H, ddd), 7.85-7.77 (3H, m), 7.57-7.40 (12H, m), 1.76 (6H, s)A1548.96 (1H, dd), 8.50 (1H, dd), 8.36 (2H, ddd), 8.25 (2H, dd), 8.17 (1H, d), 7.97 (1H, ddd), 7.89-7.77 (6H, m), 7.61-7.35 (11H, m), 7.25 (2H, dd), 1.76 (6H, s)A1818.36 (4H, ddd), 8.10-8.05 (2H, m), 7.94 (1H, d), 7.82 (1H, s), 7.63-7.34 (13H, m), 1.82 (6H, s)A1838.40 (2H,ddd), 8.26 (2H, ddd), 8.10-8.06 (2H, m), 7.96 (1H, dd), 7.80 (1H, s), 7.75 (2H, ddd), 7.63 (13H, m), 7.26 (2H, dd)A1968.95 (1H, dd), 8.50 (1H, dd), 8.38-8.35 (3H, m), 8.10-8.06 (2H, m), 7.94-7.89 (3H, m), 7.89-7.34 (17H, m), 1.8 (6H, s)A1989.10 (1H, dd), 8.49 (1H, dd), 8.16-7.94 (7H, m), 7.82 (1H, s), 7.63-7.33 (15H, m), 1.80 (6H, s)A2058.55 (1H, dd), 8.36 (2H, dd), 8.19 (1H, dd), 8.11-8.05 (2H, m), 7.95 (1H, dd), 7.82 (1H, s), 7.64-7.33 (12H, m), 7.20-7.11 (4H, m), 1.80 (6H, s)A2218.85 (1H, dd), 8.36 (4H, ddd), 7.82 (1H, s), 7.77 (1H, ddd), 7.63-7.46 (11H, m), 7.30-7.24 (2H, m), 7.09 (1H, d), 1.76 (6H, s)A2368.86 (1H, dd), 8.36 (2H, ddd), 7.99 (1H, dd), 7.82 (1H, s), 7.77 (1H, ddd), 7.64-7.30 (16H, m), 7.09 (1H, d), 1.76 (6H, s)A2468.85 (1H, dd), 7.99 (1H, dd), 7.81 (1H, s), 7.77 (1H, ddd), 7.63-7.25 (19H, m), 1.75 (6H, s)A2618.37-8.28 (5H, m), 7.85 (1H, ddd), 7.75 (1H, ddd), 7.61-7.38 (19H, m)A2818.51 (1H, dd), 8.36 (4H. ddd), 8.11 (1H, dd), 8.00 (1H, d), 7.67-7.42 (19H, m)A3018.54 (1H, dd), 8.36 (4H, ddd), 7.98 (1H, ddd), 7.62-7.42 (20H, m)A3218.36 (4H, ddd), 8.17 (1H, d), 7.97 (1H, ddd), 7.85 (1H, d), 7.77-7.75 (2H, m), 7.60-7.40 (12H, m), 1.75 (6H, s)A3318.36 (2H, ddd), 8.17 (1H, d), 7.99 (1H, dd), 7.85 (1H, d), 7.77-7.75 (2H, m), 7.60-7.31 (15H, m), 1.74 (6H, s)A3418.37 (4H, ddd), 8.10-8.06 (2H, m), 7.94 (1H, dd), 7.75 (1H, s), 7.63-7.37 (13H, m), 1.83 (6H, s)A3618.86 (1H, dd), 8.37 (4H, ddd), 7.78-7.75 (2H, m), 7.63-7.47 (11H, m), 7.30-7.24 (2H, m), 7.09 (1H, d)A3718.85 (1H, dd), 8.36 (2H, ddd), 7.99 (1H, dd), 7.77-7.74 (2H, m), 7.63-7.25 (16H, m), 7.09 (1H, d), 1.76 (6H, s)A3838.36 (4H, ddd), 7.64-7.46 (15H, m)A3848.06 (1H, dd),7.60-7.43 (9H, m)B48.97 (1H, dd), 8.18 (1H, dd), 7.79-7.75 (4H, m), 7.64-7.38 (16H, m), 7.27-7.16 (10H, m), 6.91 (1H, dd)B208.97 (1H, dd), 8.18 (1H, dd), 7.80-7.74 (6H, m), 7.64-7.38 (20H, m), 7.28-7.17 (11H, m)B658.97 (1H, dd), 8.18 (1H, dd), 7.79-7.38 (27H, m), 7.28-7.27 (6H, m)B928.97 (1H, dd), 8.18 (1H, dd), 8.03 (1H, d), 7.79-7.75 (4H, m), 7.64-7.41 (16H, m), 7.27-7.17 (9H, m), 6.91 (1H, dd)B1038.97 (1H, dd), 8.18 (1H, dd), 7.79-7.74 (8H, m), 7.64-7.38 (19H, m)B1358.97 (1H, dd), 8.18 (1H, dd), 7.79-7.74 (6H, m), 7.63-7.37 (14H, m)7.28-7.24 (6H, m), 7.09-7.00 (3H, m)B1548.97 (1H, dd), 8.18 (1H, dd), 8.08-8.02 (2H, m), 7.79-7.38 (24H, m)B1648.97-8.95 (2H, m), 8.03 (1H, s), 7.79-7.75 (6H, m), 7.56-7.41 (16H, m), 7.31-7.27 (5H, m), 6.91 (1H, dd)B2088.97 (1H, dd), 8.56 (1H, dd), 8.18 (1H, dd), 7.82-7.73 (6H, m), 7.64-7.38 (20H, m).

[0538]

[0539] 화합물FD-MS화합물FD-MSA1m / z= 614.21 (C 43 H 26 N4O, 614.71)A198m / z= 705.24 (C 50 H<h2 style=";text-align:left;direction:ltr"> 31 <h2 style=";text-align:left;direction:ltr"> N3O2, 705.82)A3m / z= 690.24 (C<h2 style=";text-align:left;direction:ltr"> 49 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 30 <h2 style=";text-align:left;direction:ltr"> N4O, 690.81)A205m / z= 654.24 (C)<h2 style=";text-align:left;direction:ltr"> 46 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 30 <h2 style=";text-align:left;direction:ltr"> N4O, 654.77)A20m / z= 704.22 (C<h2 style=";text-align:left;direction:ltr"> 49 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 28 <h2 style=";text-align:left;direction:ltr"> N4O2, 704.79)A221m / z= 565.22 (C<h2 style=";text-align:left;direction:ltr"> 40 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 27 <h2 style=";text-align:left;direction:ltr"> N3O, 565.68)A51m / z= 614.21 (C<h2 style=";text-align:left;direction:ltr"> 43 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 26 <h2 style=";text-align:left;direction:ltr"> N4O, 614.71)A236m / z= 655.23 (C)<h2 style=";text-align:left;direction:ltr"> 46 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N3O2, 655.76)A53m / z= 690.24 (C<h2 style=";text-align:left;direction:ltr"> 49 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 30 <h2 style=";text-align:left;direction:ltr"> N4O, 690.81)A246m / z= 745.24 (C)<h2 style=";text-align:left;direction:ltr"> 52 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 31 <h2 style=";text-align:left;direction:ltr"> N3O3, 745.84)A55m / z= 690.24 (C<h2 style=";text-align:left;direction:ltr"> 49 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 30 <h2 style=";text-align:left;direction:ltr"> N4O, 690.81)A261m / z= 614.21 (C)<h2 style=";text-align:left;direction:ltr"> 43 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 26 <h2 style=";text-align:left;direction:ltr"> N4O, 614.71)A69m / z= 704.22 (C<h2 style=";text-align:left;direction:ltr"> 49 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 28 <h2 style=";text-align:left;direction:ltr"> N4O2, 704.79)A281m / z= 614.21 (C<h2 style=";text-align:left;direction:ltr"> 43 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 26 <h2 style=";text-align:left;direction:ltr"> N4O, 614.71)A71m / z= 704.22 (C<h2 style=";text-align:left;direction:ltr"> 49 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 28 <h2 style=";text-align:left;direction:ltr"> N4O2, 704.79)A301m / z= 614.21 (C<h2 style=";text-align:left;direction:ltr"> 43 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 26 <h2 style=";text-align:left;direction:ltr"> N4O, 614.71)A78m / z= 703.24 (C<h2 style=";text-align:left;direction:ltr"> 49 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 29 <h2 style=";text-align:left;direction:ltr"> N5O, 703.80)A321m / z= 565.22 (C<h2 style=";text-align:left;direction:ltr"> 40 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 27 <h2 style=";text-align:left;direction:ltr"> N3O, 565.68)A83m / z= 740.26 (C<h2 style=";text-align:left;direction:ltr"> 53 <h2 style=";text-align:left;direction:ltr"> H<h2 style=";text-align:left;direction:ltr"> 32N4O, 740.87)A331m / z= 655.23 (C 46 H 29 N3O2, 655.76)A87m / z= 690.24 (C 49 H 30 N4O, 690.81)A341m / z= 565.22 (C 40 H 27 N3O, 565.68)A89m / z= 766.27 (C 55 H 34 N4O, 766.90)A361m / z= 565.22 (C 40 H 27 N3O, 565.68)A94m / z= 643.17 (C 44 H 25 N3OS, 643.76)A371m / z= 655.23 (C 46 H 29 N3O2, 655.76)A99m / z= 614.21 (C 43 H 26 N4O, 614.71)A383m / z= 621.25 (C 43 H 19 D7N4O, 621.75)A103m / z= 690.24 (C 49 H 30 N4O, 690.81)A384m / z= 630.31 (C 43 H 10 D 16 N4O, 630.81)A104m / z= 766.27 (C 55 H 34 N4O, 766.90)B4m / z= 689.27 (C 52 H 35 NO, 689.86)A115m / z= 704.22 (C 49 H 28 N4O2, 704.79)B20m / z= 765.30 (C 58 H 39 NO, 765.96)A120m / z= 720.20 (C 49 H 28 N4OS, 720.85)B65m / z= 689.27 (C 52 H 35NO, 689.86)A135m / z= 704.22 (C 49 H 28 N4O2, 704.79)B92m / z= 689.27 (C 52 H 35 NO, 689.86)A137m / z= 613.22 (C 44 H 27 N3O, 613.72)B103m / z=689.27 (C 52 H 35 NO, 689.86)A141m / z= 565.22 (C 40 H 27 N3O, 565.68)B135m / z=613.24 (C 46 H 31 NO, 613.76)A154m / z= 691.26 (C 50 H 33 N3O, 691.83)B154m / z=663.26 (C 50 H 33 NO, 663.82)A181m / z= 565.22 (C 40 H 27 N3O, 565.68)B164m / z=613.24 (C 46 H 31 NO, 613.76)A183m / z= 641.25 (C 46 H 31 N3O, 641.77)B208m / z= 778.30 (C 58 H 38 N2O, 778.95)A196m / z=691.26 (C 50 H 33 N3O, 691.83)B236m / z=637.39 (C 46 H7D 24 NO, 637.91)

[0540]

[0541] Experimental Example 1.

[0542] Experimental Example 1-1. Fabrication of an Organic Light-Emitting Device

[0543] A glass substrate coated with a 1,500 Å thick ITO film was ultrasonically cleaned in distilled water. After the distilled water cleaning, it was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UVO (Ultraviolet Ozone) for 5 minutes using UV (Ultraviolet) in a UV (Ultraviolet) cleaner. Afterwards, the substrate was transferred to a plasma cleaner (PT), and plasma treated in a vacuum to increase the ITO work function and remove residual films, and then transferred to a thermal evaporation equipment for organic vapor deposition.

[0544] A hole injection layer 4,4',4''-tris[2-naphthyl(phenyl)amino] triphenylamine (2-TNATA) and a hole transport layer N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) were deposited on the ITO transparent electrode (anode).

[0545]

[0546] On top of that, a light-emitting layer was thermally vacuum-deposited as follows. The light-emitting layer used a heterocyclic compound represented by chemical formula 1 as a host and a red phosphorescent dopant (Ir(piq)2(acac)), and the red phosphorescent dopant was doped into the host at 3% and deposited to a thickness of 500 Å.

[0547] Afterwards, BCP was deposited as a hole blocking layer with a thickness of 60 Å, and Alq3 was deposited as an electron transport layer with a thickness of 250 Å on top of it. Finally, lithium fluoride (LiF) was deposited as an electron injection layer with a thickness of 10 Å on the electron transport layer, and then aluminum (Al) was deposited as a cathode with a thickness of 1,200 Å on the electron injection layer, thereby manufacturing an organic electroluminescent device.

[0548]

[0549] Meanwhile, all organic compounds required for OLED device production are 10 for each material. -6 ~10 -8 It was purified by vacuum sublimation under 10 torr and used in the production of OLED (Organic Light Emitting Device).

[0550]

[0551] Experimental Example 1-2. Driving voltage, luminous efficiency, and lifespan of organic light-emitting devices

[0552] The electroluminescence (EL) characteristics of the organic light-emitting device manufactured as described above were measured using M7000 from MaxScience, and the standard luminance was determined to be 6,000 cd / m using the lifespan measurement equipment (M6000) manufactured by MaxScience based on the measurement results. 2 When, T 90 The results of measuring the driving voltage, luminous efficiency, color coordinates (CIE), and lifespan of the organic light-emitting device manufactured according to the present invention are shown in Table 6 below.

[0553] The above T 90 refers to the lifespan (unit: hours), which is the time it takes for the initial brightness to drop to 90%.

[0554]

[0555] Compound threshold voltage (V) on )driving voltage (V) op )Efficiency (cd / A)Color coordinates (x, y)Lifespan (T 90) Comparative Example 1A3.386.257.2(0.681, 0.317)14 Comparative Example 2B3.366.176.5(0.680, 0.319)9 Comparative Example 3C3.316.146.8(0.682, 0.318)9 Comparative Example 4D3.756.545.3(0.679, 0.320)3 Comparative Example 5E3.586.396.4(0.680, 0.318)7 Comparative Example 6F3.546.346.1(0.677, 0.321)10 Comparative Example 7G3.456.2410.1(0.678, 0.320)8 Comparative Example 8H3.386.096.3(0.680, 0.319)6Comparative Example 9I3.646.495.5(0.683, 0.316)4Comparative Example 10J3.646.576.7(0.678, 0.322)7Comparative Example 11K3.626.486.8(0.678, 0.321)6Comparative Example 12L3.576.427.0(0.677, 0.323)7Comparative Example 13M3.756.515.1(0.678, 0.320)4Example 1A12.745.7526.4(0.682, 0.317)40Example 2A32.725.7226.8(0.679, 0.320)42Example 3A202.705.7127.5(0.679, 0.321)40Example 4A512.575.5829.7(0.682, 0.317)47Example 5A532.545.5629.5(0.683, 0.316)49Example 6A552.555.5128.7(0.682, 0.318)47Example 7A692.535.5329.9(0.681, 0.317)46Example 8A712.555.5827.6(0.681, 0.317)50 Example 9A782.555.5628.9(0.680, 0.319)45 Example 10A832.555.5729.2(0.682, 0.317)51 Example 11A872.535.5528.7(0.681, 0.318)47 Example 12A892.505.4827.9(0.680, 0.319)46 Example 13A942.675.7126.9(0.677, 0.323)36 Example 14A992.655.6428.3(0.676, 0.323)44 Example 15A1032.695.6827.7(0.680, 0.319)42Example 16A1042.685.6627.9(0.680, 0.318)40 Example 17A1 152.63 5.61 28.2 (0.683, 0.316)43 Example 18A1 202.65 5.60 27.9 (0.680, 0.319)40 Example 19A1 352.68 5.64 27.5 (0.678, 0.321)43 Example 20A1 372.75 5.77 25.3 (0.678, 0.321)35 Example 21A1 412.79 5.84 24.5 (0.681, 0.318)28 Example 22A1 542.81 5.83 25.1 (0.683, 0.317)34 Example 23A1812.775.8025.8(0.682, 0.317)35Example 24A1832.755.8226.0(0.679, 0.320)37Example 25A1962.785.8526.2(0.681, 0.317)34Example 26A1982.755.7726.0(0.679, 0.320)38Example 27A2052.745.7526.1(0.681, 0.317)34Example 28A2212.805.8225.2(0.680, 0.319)33Example 29A2362.815.8324.9(0.680, 0.320)32 Example 30A2462.765.7925.6(0.679, 0.320)35 Example 31A2612.935.9720.5(0.680, 0.320)27 Example 32A2812.875.9222.2(0.680, 0.320)29 Example 33A3012.905.9421.1(0.681, 0.318)29 Example 34A3212.865.9123.1(0.682, 0.317)24 Example 35A3312.855.9623.0(0.681, 0.319)25Example 36A3412.835.8623.7(0.681, 0.317)25Example 37A3612.855.8823.6(0.679, 0.318)22Example 38A3712.845.8623.7(0.680, 0.319)23Example 39A3832.565.5830.2(0.681, 0.319)52Example 40A3842.575.5431.7(0.683, 0.317)57.

[0556]

[0557] The comparative compounds used in Table 6 above are as follows.

[0558]

[0559] From the results in Table 6 above, the organic light-emitting device including the heterocyclic compound represented by the chemical formula 1 of the present invention in the organic layer showed low driving voltage and excellent luminous efficiency and lifespan.

[0560] Specifically, the heterocyclic compound represented by chemical formula 1 of the present invention is characterized by high efficiency and long life.

[0561] Compared to Compound A of Comparative Example 1 and Compound F of Comparative Example 6, the heterocyclic compound represented by Chemical Formula 1 of the present invention has an electron transport group (ET), N-Het, positioned at position 1 of benzofuran, thereby forming steric hindrance between the basic skeleton and N-Het, thereby improving the charge balance within the molecule. Accordingly, the performance of the organic light-emitting device can be improved.

[0562] Compound B of Comparative Example 2, Compound C of Comparative Example 3, Compound E of Comparative Example 5, Compound K of Comparative Example 11, and Compound L of Comparative Example 12 were hosts in which the HOMO and LUMO regions were in contact, and the flow of electrons and holes within the molecule was in contact, resulting in a lot of electrical damage and poor thermal stability and lifespan.

[0563] Compound D of Comparative Example 4 and Compound M of Comparative Example 13 are indolocarbazole-based p-Hosts and do not contain N-Het. Compound D of Comparative Example 4 and Compound M of Comparative Example 13 showed poor hole injection capabilities due to their wide band gaps, resulting in increased driving voltage and decreased efficiency.

[0564] Compound G of Comparative Example 7 and Compound H of Comparative Example 8 have structures in which furan and thiophene are partially substituted in the basic skeleton, unlike the heterocyclic compound represented by Chemical Formula 1 of the present invention. That is, X1 or X2 is O or S, and compared to the partially substituted structure of the heterocyclic compound represented by Chemical Formula 1 of the present invention in which X1 or X2 has NAr1 or CRaRb, the electron mobility of the molecule is excessively fast, resulting in a breakdown in the charge balance of the light-emitting layer and a deterioration in the performance of the organic light-emitting device.

[0565] Compound I of Comparative Example 9 showed a decrease in material stability and a reduced lifespan during deposition due to the adamantane substituent and excessively large molecular weight.

[0566] Compound J of Comparative Example 10 showed a result in which the performance of the organic light-emitting device was deteriorated due to the strain created in the structure itself, including the basic skeleton that induces hydrogen bonding between oxygen and hydrogen.

[0567] From this, it was confirmed that the heterocyclic compound represented by the chemical formula 1 of the present invention has a low driving voltage and excellent luminous efficiency and lifespan characteristics.

[0568]

[0569] Experimental example 2.

[0570] Experimental Example 2-1. Fabrication of an Organic Light-Emitting Device

[0571] An organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1, except that the light-emitting layer was deposited from a single source after preliminarily mixing one type of first host (heterocyclic compound represented by Chemical Formula 1, N type) and one type of second host (heterocyclic compound represented by Chemical Formula 3, P type) described in Table 7 below.

[0572]

[0573] Experimental Example 2-2. Driving Voltage and Luminous Efficiency of Organic Light-Emitting Devices

[0574] The electroluminescence (EL) characteristics of the organic light-emitting device manufactured as described above were measured using M7000 from MaxScience, and the standard luminance was determined to be 6,000 cd / m using the lifespan measurement equipment (M6000) manufactured by MaxScience based on the measurement results. 2 When, T 90 The results of measuring the driving voltage, luminous efficiency, color coordinates (CIE), and lifespan of the organic light-emitting device manufactured according to the present invention are shown in Table 7 below.

[0575] The above T 90 refers to the lifespan (unit: hours), which is the time it takes for the initial brightness to drop to 90%.

[0576]

[0577] Compound ratio (p:n) threshold voltage (V) on )driving voltage (V) op )Efficiency (cd / A)Color coordinates (x, y)Lifespan (T 90) Comparative Example 14B20:A1:13.025.8613.5(0.681, 0.317)17 Comparative Example 15B4:B1:13.015.8912.6(0.680, 0.319)10 Comparative Example 16B154:C1:12.955.8412.9(0.682, 0.318)11 Comparative Example 17B135:D1:13.576.366.7(0.679, 0.320)4 Comparative Example 18B4:E1:13.346.1110.4(0.680, 0.318)7 Comparative Example 19B103:F1:13.376.149.8(0.677, 0.321)8Comparative example 20B4:G1:12.895.8313.1(0.678, 0.320)15Comparative example 21B65:H1:12.845.80.11.7(0.680, 0.319)9Comparative example 22B103:I1:13.316.177.6(0.683, 0.316)6Comparative example 23B4:J1:13.366.2410.3(0.678, 0.322)10Comparative example 24B92:K1:13.256.149.5(0.678, 0.321)8Comparative example 25B164:L1:13.196.1010.1(0.677, 0.323)9Comparative Example 26B135:M1:13.466.376.3(0.678, 0.320)5Example 41B4:A11:12.525.5641.2(0.682, 0.317)51Example 42B20:A31:12.515.5541.8(0.679, 0.320)55Example 43B65:A201:12.505.5342.1(0.679, 0.321)50Example 44B164:A511:12.405.3945.6(0.682, 0.317)61 Example 45 B154: A53 1: 12.38 5.36 45.4 (0.683, 0.316)63 Example 46 B92: A55 1: 12.39 5.38 45.9 (0.682, 0.319)60 Example 47 B103: A69 1: 12.35 5.34 47.2 (0.681, 0.317)60 Example 48 B103: A71 1: 12.38 5.39 45.6 (0.681, 0.319)62 Example 49 B65: A78 1: 12.34 5.32 47.1 (0.680, 0.319)56 Example 50B103:A831:12.345.3546.8(0.682, 0.317)65 Example 51B92:A871:12.365.3146.9(0.681, 0.318)57 Example 52 B103:A891:12.355.3046.6(0.682, 0.318)55 Example 53 B65:A941:12.655.6240.2(0.677, 0.323)41 Example 54 B154:A991:12.485.4943.6(0.676, 0.323)59 Example 55 B208:A1031:12.565.5941.7(0.680, 0.319)46 Example 56 B164:A1041:12.575.6242.1(0.681, 0.318)45 Example 57 B92:A1151:12.465.4843.9(0.683, 0.316)55 Example 58 B65:A1201:12.435.4441.9(0.680, 0.319)52 Example 59 B103:A1351:12.515.5242.2(0.678, 0.321)53 Example 60 B4:A1371:12.725.7938.4(0.678, 0.321)42 Example 61 B164:A1411:12.625.6336.8(0.681, 0.318)40 Example 62B65:A1541:12.615.6437.4(0.683, 0.317)44 Example 63B135:A1811:12.605.6239.2(0.682, 0.317)44 Example 64B135:A1831:12.595.6139.1(0.680, 0.318)45 Example 65B65:A1961:12.565.5738.7(0.681, 0.319)43 Example 66B103:A1981:12.575.5940.1(0.679, 0.320)47 Example 67B164:A2051:12.585.6241.2(0.682, 0.318)44Example 68B4:A2211:12.625.6438.7(0.680, 0.319)45Example 69B20:A2361:12.615.6338.9(0.683, 0.316)46Example 70B20:A2461:12.555.5940.3(0.679, 0.320)48Example 71B92:A2611:12.695.7430.7(0.680, 0.320)32Example 72B154:A2811:12.655.7032.1(0.680, 0.320)36 Example 73B208:A3011:12.685.7231.2(0.680, 0.320)33 Example 74B164:A3211:12.665.6833.5(0.682, 0.317)35 Example 75B4:A3311:12.655.6733.7(0.681, 0.318)34 Example 76B154:A3411:12.635.6934.2(0.681, 0.317)38 Example 77B135:A3611:12.645.6734.3(0.679, 0.318)36 Example 78B20:A3711:12.645.6534.2(0.682, 0.318)39 Example 79 B164:A383 1:12.39 5.40 47.3 (0.681, 0.319)65 Example 80 B164:A384 1:12.39 5.39 47.9 (0.683, 0.317)73.

[0578]

[0579] Comparing the results of Table 7 above with the results of Table 6 above, it can be confirmed that when the heterocyclic compound represented by Chemical Formula 1 of the present invention and the heterocyclic compound represented by Chemical Formula 3 are simultaneously used as a host for the light-emitting layer, the driving voltage, luminous efficiency, and lifespan are all improved.

[0580] From this, it can be expected that an exciplex phenomenon will occur when heterocyclic compounds represented by chemical formulas 1 and 3 are simultaneously included.

[0581] The above exciplex phenomenon is a phenomenon in which energy of the size of the HOMO level of the donor (p-host) and the LUMO level of the acceptor (n-host) is released due to electron exchange between two molecules. When the exciplex phenomenon between two molecules occurs, reverse intersystem crossing (RISC) occurs, and this can increase the internal quantum efficiency of fluorescence up to 100%. When a donor with a good hole transport ability and an acceptor with a good electron transport 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, so the driving voltage can be lowered, which can help improve the lifespan.

[0582] In the present invention, it was confirmed that when a heterocyclic compound represented by the above chemical formula 3 was used as a donor and a heterocyclic compound represented by the above chemical formula 1 was used as an acceptor, excellent device characteristics were exhibited.

[0583] On the other hand, when the comparative example compound is used simultaneously with the heterocyclic compound represented by chemical formula 3, it can be seen that the performance in terms of driving voltage, luminous efficiency, and lifespan is lower than that of the example.

[0584] That is, when the heterocyclic compound represented by the chemical formula 1 of the present invention and the heterocyclic compound represented by the chemical formula 3 are simultaneously used as a host for the light-emitting layer, it can be confirmed that the driving voltage is low and the light-emitting efficiency and lifespan are remarkably excellent.

[0585]

[0586] [Explanation of symbols]

[0587] 100: Substrate

[0588] 200: Bipolar

[0589] 300: Organic layer

[0590] 301: Hole injection layer

[0591] 302: Hole transport layer

[0592] 303: Emissive layer

[0593] 304: Hole blocking layer

[0594] 305: Electron transport layer

[0595] 306: Electron injection layer

[0596] 400: Cathode

Claims

1. A heterocyclic compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, The above X1 and X2 are different from each other and are each independently a direct bond; NAr1; or CRaRb, Either of the above X1 and X2 is a direct bond, wherein R1 to R4, Ra and Rb are the same as or different from each other, and each independently represent hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R101R102; -SiR101R102R103; And -NR101R102, or two or more adjacent groups are combined to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same as or different from each other and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, The above a is an integer from 0 to 6, and when a is 2 or greater, R1 is equal to or different from each other, The above b is an integer from 0 to 3, and when b is 2 or greater, R3 are equal to or different from each other, The above Ar1 is a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, The above L1 is a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, The above c is an integer from 0 to 5, and when c is 2 or greater, L1 is equal to or different from each other, The above N-Het is a substituted or unsubstituted C2 to C60 monocyclic or polycyclic heterocyclic group containing two or more N.

2. In paragraph 1, The heterocyclic compound represented by the above chemical formula 1 is a heterocyclic compound represented by the following chemical formula 1-1 or chemical formula 1-2: [Chemical Formula 1-1] [Chemical Formula 1-2] In the above chemical formulas 1-1 and 1-2, The above X1, X2, R1 to R4, L1, a to c and N-Het are the same as defined in the above chemical formula 1.

3. In paragraph 2, The heterocyclic compound represented by the above chemical formula 1-1 is represented by any one of the following chemical formulas 1-1a to 1-1c: The heterocyclic compound represented by the above chemical formula 1-2 is a heterocyclic compound represented by any one of the following chemical formulas 1-2a to 1-2c: [Chemical Formula 1-1a] [Chemical Formula 1-1b] [Chemical Formula 1-1c] [Chemical Formula 1-2a] [Chemical Formula 1-2b] [Chemical formula 1-2c] In the above chemical formulas 1-1a to 1-1c and chemical formulas 1-2a to 1-2c, The above X1, X2, R1 to R4, L1, a to c and N-Het are the same as defined in the above chemical formula 1.

4. In paragraph 1, The above R3 is hydrogen; deuterium; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, A heterocyclic compound, wherein when the above b is 2 or more, R3 is the same or different.

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

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

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

8. In paragraph 7, The above organic layer includes a light-emitting layer, An organic light-emitting device, wherein the light-emitting layer comprises a heterocyclic compound according to any one of claims 1 to 6.

9. In paragraph 7, An organic light-emitting device, wherein the organic layer further comprises a heterocyclic compound represented by the following chemical formula 3: [Chemical Formula 3] In the above chemical formula 3, wherein R31 and R32 are the same as or different from each other, and each independently represent hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R301R302; -SiR301R302R303; And -NR301R302, 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 R301, R302 and R303 are the same as or different from each other and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, The above g is an integer from 0 to 3, and when g is 2 or greater, R31 are equal to or different from each other, The above h is an integer from 0 to 5, and when h is 2 or greater, R32 are equal to or different from each other, The above L31 to L34 are the same as or different from each other, and each independently represents a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, The above i is an integer from 0 to 5, and when i is 2 or greater, L31 are equal to or different from each other, The above j is an integer from 0 to 5, and when j is 2 or greater, L32 are equal to or different from each other, The above k is an integer from 0 to 5, and when k is 2 or greater, L33 are equal to or different from each other, The above l is an integer from 0 to 5, and when l is 2 or greater, L34 are equal to or different from each other, The above Ar31 to Ar33 are the same as or different from each other, and each independently represents a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

10. In paragraph 9, The heterocyclic compound represented by the above chemical formula 3 is an organic light-emitting device represented by the following chemical formula 3-1 or chemical formula 3-2: [Chemical Formula 3-1] [Chemical Formula 3-2] In the above chemical formulas 3-1 and 3-2, The above R31, R32, L31 to L34, Ar31 to Ar33 and g to l are the same as defined in the above chemical formula 3.

11. In paragraph 9, An organic light-emitting device in which the heterocyclic compound represented by the above chemical formula 3 does not contain deuterium as a substituent or has a deuterium content of 1% to 100% with respect to the total number of hydrogen atoms and deuterium atoms.

12. In paragraph 9, The heterocyclic compound represented by the above chemical formula 3 is an organic light-emitting device represented by any one of the following compounds: .

13. In paragraph 9, The above organic layer includes a light-emitting layer, An organic light-emitting device, wherein the light-emitting layer comprises a heterocyclic compound according to any one of claims 1 to 6 and a heterocyclic compound represented by the chemical formula 3.

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

15. A composition for an organic layer comprising a heterocyclic compound according to any one of claims 1 to 6 and a heterocyclic compound represented by the following chemical formula 3: [Chemical Formula 3] In the above chemical formula 3, wherein R31 and R32 are the same as or different from each other, and each independently represent hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R301R302; -SiR301R302R303; And -NR301R302, 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 R301, R302 and R303 are the same as or different from each other and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, The above g is an integer from 0 to 3, and when g is 2 or greater, R31 are equal to or different from each other, The above h is an integer from 0 to 5, and when h is 2 or greater, R32 are equal to or different from each other, The above L31 to L34 are the same as or different from each other, and each independently represents a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, The above i is an integer from 0 to 5, and when i is 2 or greater, L31 are equal to or different from each other, The above j is an integer from 0 to 5, and when j is 2 or greater, L32 are equal to or different from each other, The above k is an integer from 0 to 5, and when k is 2 or greater, L33 are equal to or different from each other, The above l is an integer from 0 to 5, and when l is 2 or greater, L34 are equal to or different from each other, The above Ar31 to Ar33 are the same as or different from each other, and each independently represents a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

16. In paragraph 15, A composition for an organic layer, wherein the weight ratio of the heterocyclic compound represented by the chemical formula 1 above and the heterocyclic compound represented by the chemical formula 3 above is 1:9 to 9:1.

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