Heterocyclic compound and organic light-emitting device comprising same

Abstract

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

Description

Heterocyclic compound and organic light-emitting device containing the same

[0001] This application claims the benefit of priority to Korean Patent Application No. 10-2023-0156207, dated November 13, 2023, the entire contents of which are incorporated herein by reference.

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

[0003]

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

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

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

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

[0008]

[0009] [Previous literature]

[0010] [Patent Document]

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

[0012]

[0013] The present invention seeks to provide a heterocyclic compound and an organic light-emitting device comprising the same.

[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 the same or different from each other, and are each independently O; or S,

[0021] wherein R1 to R3, R5 and R6 are the same as or different from each other, and each independently represent hydrogen; deuterium; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; -P(=O)R101R102; -SiR101R102R103; -NR101R102; or are selected from the group consisting of the following chemical formula 2; and the following chemical formula 3, or are selected from the group consisting of two or more adjacent groups bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring; Or forms a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same as or different from each other, and each independently represents a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0022] Either of the above R1 and R6 is the following chemical formula 2; or the following chemical formula 3,

[0023] The above R4 is the following chemical formula 2; or the following chemical formula 3,

[0024] The above R1, R4 and R6 are different from each other,

[0025] The above a is an integer from 0 to 3, and when a is 2 or greater, R2 are equal to or different from each other,

[0026] The above b is an integer from 0 to 3, and when b is 2 or greater, R5 are equal to or different from each other,

[0027] [Chemical Formula 2]

[0028]

[0029] [Chemical Formula 3]

[0030]

[0031] In the above chemical formulas 2 and 3,

[0032] The above L1 to L4 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,

[0033] 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,

[0034] The above d is an integer from 0 to 5, and when d is 2 or greater, L2 is equal to or less than each other,

[0035] The above e is an integer from 0 to 5, and when e is 2 or greater, L3 are equal to or different from each other,

[0036] The above f is an integer from 0 to 5, and when f is 2 or greater, L4 are equal to or different from each other,

[0037] The above Ar1 to Ar3 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.

[0038]

[0039] In addition, the present invention

[0040] First electrode;

[0041] A second electrode provided opposite to the first electrode; and

[0042] An organic light-emitting device comprising at least one organic layer provided between the first electrode and the second electrode,

[0043] 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.

[0044] In addition, the present invention provides an organic light-emitting device in which the organic layer includes a hole transport layer, and the hole transport layer includes the heterocyclic compound.

[0045] In addition, the present invention provides an organic light-emitting device in which the organic layer includes an electron blocking layer, and the electron blocking layer includes the heterocyclic compound.

[0046]

[0047] 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, an electron blocking layer material, a hole transport layer material, an emitting layer material, an electron transport layer material, a hole blocking layer material, an electron injection layer material, etc. in the organic light-emitting device. In particular, the compound can be used as a hole transport layer material, an electron blocking layer material, or an emitting layer material of an organic light-emitting device.

[0048] Specifically, the compound represented by the above chemical formula 1 has fast hole mobility and has an appropriate HOMO (Highest Occupied Molecular Orbital) level and a high LUMO (Lowest Unoccupied Molecular Orbital) level, thereby lowering the driving voltage and improving luminous efficiency and lifespan characteristics.

[0049]

[0050] Figures 1 to 3 are drawings schematically showing the laminated structure of an organic light-emitting device according to one embodiment of the present invention.

[0051]

[0052] Hereinafter, the present invention will be described in more detail.

[0053]

[0054] 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.

[0055] In this specification, "substituted or unsubstituted" means deuterium; halogen; cyano group; straight or branched chain alkyl group having a carbon atom of 1 to 60 carbon atoms; straight or branched chain alkenyl group having a carbon atom of 2 to 60 carbon atoms; straight or branched chain alkynyl group having a carbon atom of 2 to 60 carbon atoms; straight, branched or cyclic alkyl group having a carbon atom of 1 to 60 carbon atoms; monocyclic or polycyclic cycloalkyl group having a carbon atom of 3 to 60 carbon atoms; monocyclic or polycyclic heterocycloalkyl group having a carbon atom of 2 to 60 carbon atoms; monocyclic or polycyclic aryl group having a carbon atom of 6 to 60 carbon atoms; monocyclic or polycyclic heteroaryl group having a carbon atom of 2 to 60 carbon atoms; -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.

[0056] In this specification, halogen may be fluorine; chlorine; bromine; or iodine.

[0057] 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.

[0058] 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.

[0059] 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.

[0060] 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.

[0061] In the present specification, a cycloalkyl group includes a monocyclic or polycyclic group having 3 to 60 carbon atoms, and may be further substituted by another substituent. Here, polycyclic means a group in which a cycloalkyl group is directly connected to or condensed with another ring group. Here, the other ring group may be a cycloalkyl group, but may also be another type of ring group, such as a heterocycloalkyl group; an aryl group; a heteroaryl group, etc. The cycloalkyl group may have 3 to 60 carbon atoms, specifically 3 to 40 carbon atoms, and more specifically 5 to 20 carbon atoms. Specifically, 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.

[0062] 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.

[0063] In the present specification, an aryl group includes a monocyclic or polycyclic ring having 6 to 60 carbon atoms, and may be further substituted by another substituent. Here, polycyclic means a group in which an aryl group is directly connected to or condensed with another ring group. Here, the other ring group may be an aryl group, but may also be another type of ring group, such as a cycloalkyl group; a heterocycloalkyl group; a heteroaryl group, etc. The aryl group may include a spiro group. The aryl group may have 6 to 60 carbon atoms, specifically 6 to 40 carbon atoms, and more specifically 6 to 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.

[0064] 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.

[0065] 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.

[0066] In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be combined with each other to form a ring.

[0067] In the present specification, when the fluorenyl group is substituted, It can be, but is not limited to, the following.

[0068] 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.

[0069]

[0070] In the present specification, a heteroaryl group includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms and a heteroatom selected from S, O, Se, N or Si, 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.

[0071] 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.

[0072] 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.

[0073] As used herein, the term "adjacent" may refer to a substituent substituted on an atom directly connected to the atom substituted by the substituent, a substituent sterically closest to the substituent, or another substituent substituted on the atom substituted by the substituent. For example, two substituents substituted at ortho positions in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring may be interpreted as "adjacent" to each other.

[0074] 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.

[0075] 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%.

[0076] 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.”

[0077] 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.

[0078] 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.

[0079] 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.

[0080] 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.

[0081]

[0082]

[0083] 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.

[0084] 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, phenyl, biphenyl, terphenyl, triphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, azulene, etc., and includes all aromatic hydrocarbon ring compounds known in the art that satisfy the above carbon number.

[0085]

[0086] The present invention provides a heterocyclic compound represented by the following chemical formula 1.

[0087] [Chemical Formula 1]

[0088]

[0089] In the above chemical formula 1,

[0090] The above X1 and X2 are the same or different from each other, and are each independently O; or S,

[0091] wherein R1 to R3, R5 and R6 are the same as or different from each other, and each independently represent hydrogen; deuterium; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; -P(=O)R101R102; -SiR101R102R103; -NR101R102; or are selected from the group consisting of the following chemical formula 2; and the following chemical formula 3, or are substituted or unsubstituted C6 to C60 aromatic hydrocarbon rings in which two or more adjacent groups are bonded to each other; Or forms a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same as or different from each other, and each independently represents a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0092] Either of the above R1 and R6 is the following chemical formula 2; or the following chemical formula 3,

[0093] The above R4 is the following chemical formula 2; or the following chemical formula 3,

[0094] The above R1, R4 and R6 are different from each other,

[0095] The above a is an integer from 0 to 3, and when a is 2 or greater, R2 are 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, R5 are equal to or different from each other,

[0097] [Chemical Formula 2]

[0098]

[0099] [Chemical Formula 3]

[0100]

[0101] In the above chemical formulas 2 and 3,

[0102] The above L1 to L4 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,

[0103] 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,

[0104] The above d is an integer from 0 to 5, and when d is 2 or greater, L2 is equal to or less than each other,

[0105] The above e is an integer from 0 to 5, and when e is 2 or greater, L3 are equal to or different from each other,

[0106] The above f is an integer from 0 to 5, and when f is 2 or greater, L4 are equal to or different from each other,

[0107] The above Ar1 to Ar3 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.

[0108]

[0109] In one embodiment of the present invention, X1 may be O and X2 may be O.

[0110] In another embodiment of the present invention, X1 may be O and X2 may be S.

[0111] In another embodiment of the present invention, X1 may be S and X2 may be O.

[0112] In another embodiment of the present invention, X1 may be S and X2 may be S.

[0113]

[0114] In one embodiment of the present invention, R1 to R3, R5 and R6 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; -P(=O)R101R102; -SiR101R102R103; -NR101R102; or Formula 2; or Formula 3, or two or more adjacent groups bond to each other to form a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring; Or form 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.

[0115] In another embodiment of the present invention, R1 to R3, R5 and R6 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; -P(=O)R101R102; -SiR101R102R103; -NR101R102; or Formula 2; or Formula 3, or two or more adjacent groups bond to each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring; Or form 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.

[0116] In another embodiment of the present invention, R1 to R3, R5 and R6 are the same as or different from each other, and each independently represent hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C2 to C20 alkenyl group; a substituted or unsubstituted C2 to C20 alkynyl group; a substituted or unsubstituted C1 to C20 alkoxy group; a substituted or unsubstituted C3 to C20 cycloalkyl group; a substituted or unsubstituted C2 to C20 heterocycloalkyl group; -P(=O)R101R102; -SiR101R102R103; -NR101R102; or Formula 2; or Formula 3, or R101, R102 and R103 are the same as or different from each other, and each independently represent 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.

[0117] In another embodiment of the present invention, R1 to R3, R5 and R6 may be the same as or different from each other, and may each independently be hydrogen; deuterium; the above chemical formula 2; or the above chemical formula 3.

[0118] In another embodiment of the present invention, R2, R3 and R5 are the same as or different from each other, and may each independently be hydrogen or deuterium.

[0119] In another embodiment of the present invention, R1 and R6 are different from each other and can each independently be hydrogen; deuterium; the above chemical formula 2; or the above chemical formula 3.

[0120] In another embodiment of the present invention, R1 and R6 are different from each other, and one of R1 and R6 may be represented by the above chemical formula 2; or the above chemical formula 3, and the other may be hydrogen; or deuterium.

[0121] In another embodiment of the present invention, R1 may be the chemical formula 2; or the chemical formula 3; and R6 may be hydrogen; or deuterium.

[0122] In another embodiment of the present invention, R1 may be hydrogen or deuterium, and R6 may be formula 2 or formula 3.

[0123]

[0124] In one embodiment of the present invention, R4 is the chemical formula 2, one of R1 and R6 is the chemical formula 3, and the other may be hydrogen or deuterium.

[0125] In another embodiment of the present invention, R4 is the above chemical formula 2, R1 is the above chemical formula 3, and R6 may be hydrogen or deuterium.

[0126] In another embodiment of the present invention, R4 may be the chemical formula 2, R1 may be hydrogen or deuterium, and R6 may be the chemical formula 3.

[0127] In another embodiment of the present invention, R4 is the chemical formula 3, one of R1 and R6 is the chemical formula 2, and the other may be hydrogen or deuterium.

[0128] In another embodiment of the present invention, R4 is the chemical formula 3, R1 is the chemical formula 2, and R6 may be hydrogen or deuterium.

[0129] In another embodiment of the present invention, R4 may be the chemical formula 3, R1 may be hydrogen or deuterium, and R6 may be the chemical formula 2.

[0130]

[0131] In one embodiment of the present invention, L1 to L4 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.

[0132] In another embodiment of the present invention, L1 to L4 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.

[0133] In another embodiment of the present invention, L1 to L4 may be the same as or different from each other, and may each independently be a direct bond; or a substituted or unsubstituted C6 to C20 arylene group.

[0134] In another embodiment of the present invention, L1 to L4 are the same as or different from each other, and may each independently be a direct bond; or a substituted or unsubstituted phenylene group.

[0135]

[0136] In one embodiment of the present invention, Ar1 to Ar3 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.

[0137] In another embodiment of the present invention, Ar1 to Ar3 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.

[0138] In another embodiment of the present invention, Ar1 to Ar2 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 naphthyl group; a substituted or unsubstituted anthracenyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted spirobifluorenyl group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group, and the fluorenyl group may be a fluorenyl group substituted or unsubstituted with a methyl group; or a fluorenyl group substituted or unsubstituted with a phenyl group.

[0139] In another embodiment of the present invention, Ar3 may be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group.

[0140]

[0141] In one embodiment of the present invention, the heterocyclic compound represented by the chemical formula 1 may be a heterocyclic compound represented by any one of the following chemical formulas 1-1 to 1-4.

[0142] [Chemical Formula 1-1]

[0143]

[0144] [Chemical Formula 1-2]

[0145]

[0146] [Chemical Formula 1-3]

[0147]

[0148] [Chemical Formula 1-4]

[0149]

[0150] In the above chemical formulas 1-1 to 1-4,

[0151] wherein R11 and R12 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,

[0152] The above g is an integer from 0 to 4, and when g is 2 or greater, R11 are equal to or different from each other,

[0153] The above h is an integer from 0 to 4, and when h is 2 or greater, R12 are equal to or different from each other,

[0154] The above X1, X2, R2, R3, R5, a and b are the same as the definitions in the above chemical formula 1,

[0155] The above L1 to L3, c to e, Ar1 and Ar2 are the same as the definitions in the above chemical formula 2,

[0156] The above L4, f and Ar3 are the same as defined in the above chemical formula 3.

[0157]

[0158] In one embodiment of the present invention, R11 and R12 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.

[0159] In another embodiment of the present invention, R11 and R12 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 are bonded to each other to form a substituted or unsubstituted C6 to C30 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 C30 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0160] In another embodiment of the present invention, R11 and R12 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 R101, R102 and R103 may be the same as or different from each other, and each independently represent 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.

[0161] In another embodiment of the present invention, R11 and R12 are the same as or different from each other, and each independently may be hydrogen or deuterium.

[0162]

[0163] In one embodiment of the present invention, the heterocyclic compound represented by the chemical formula 1-1 may be a heterocyclic compound represented by any one of the following chemical formulas 1-1a to 1-1d.

[0164] [Chemical Formula 1-1a]

[0165]

[0166] [Chemical Formula 1-1b]

[0167]

[0168] [Chemical Formula 1-1c]

[0169]

[0170] [Chemical Formula 1-1d]

[0171]

[0172] In the above chemical formulas 1-1a to 1-1d,

[0173] The above X1, X2, R2, R3 and a are the same as the definitions in the above chemical formula 1,

[0174] The above L1 to L3, c to e, Ar1 and Ar2 are the same as the definitions in the above chemical formula 2,

[0175] The above L4, f and Ar3 are the same as the definitions of the above chemical formula 3,

[0176] The above R11 and g are the same as defined in the above chemical formula 1-1.

[0177]

[0178] In one embodiment of the present invention, in the heterocyclic compound represented by the chemical formula 1-1a, X1 may be O and X2 may be O.

[0179] In one embodiment of the present invention, in the heterocyclic compound represented by the chemical formula 1-1b, X1 may be O and X2 may be S.

[0180] In one embodiment of the present invention, in the heterocyclic compound represented by the chemical formula 1-1c, X1 may be S and X2 may be O.

[0181] In one embodiment of the present invention, in the heterocyclic compound represented by the chemical formula 1-1d, X1 may be S and X2 may be S.

[0182]

[0183] In one embodiment of the present invention, the heterocyclic compound represented by the chemical formula 1-2 may be a heterocyclic compound represented by any one of the following chemical formulas 1-2a to 1-2d.

[0184] [Chemical Formula 1-2a]

[0185]

[0186] [Chemical Formula 1-2b]

[0187]

[0188] [Chemical Formula 1-2c]

[0189]

[0190] [Chemical Formula 1-2d]

[0191]

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

[0193] The above X1, X2, R2, R3 and a are the same as the definitions in the above chemical formula 1,

[0194] The above L1 to L3, c to e, Ar1 and Ar2 are the same as the definitions in the above chemical formula 2,

[0195] The above L4, f and Ar3 are the same as the definitions of the above chemical formula 3,

[0196] The above R11 and g are the same as defined in the above chemical formula 1-2.

[0197]

[0198] In one embodiment of the present invention, in the heterocyclic compound represented by the chemical formula 1-2a, X1 may be O and X2 may be O.

[0199] In one embodiment of the present invention, in the heterocyclic compound represented by the chemical formula 1-2b, X1 may be O and X2 may be S.

[0200] In one embodiment of the present invention, in the heterocyclic compound represented by the above chemical formula 1-2c, X1 may be S and X2 may be O.

[0201] In one embodiment of the present invention, in the heterocyclic compound represented by the chemical formula 1-2d, X1 may be S and X2 may be S.

[0202]

[0203] In one embodiment of the present invention, the heterocyclic compound represented by the chemical formula 1-3 may be a heterocyclic compound represented by any one of the following chemical formulas 1-3a to 1-3d.

[0204] [Chemical Formula 1-3a]

[0205]

[0206] [Chemical Formula 1-3b]

[0207]

[0208] [Chemical Formula 1-3c]

[0209]

[0210] [Chemical Formula 1-3d]

[0211]

[0212] In the above chemical formulas 1-3a to 1-3d,

[0213] The above X1, X2, R3, R5 and b are the same as the definitions in the above chemical formula 1,

[0214] The above L1 to L3, c to e, Ar1 and Ar2 are the same as the definitions in the above chemical formula 2,

[0215] The above L4, f and Ar3 are the same as the definitions of the above chemical formula 3,

[0216] The above R12 and h are the same as defined in the above chemical formula 1-3.

[0217]

[0218] In one embodiment of the present invention, in the heterocyclic compound represented by the chemical formula 1-3a, X1 may be O and X2 may be O.

[0219] In one embodiment of the present invention, in the heterocyclic compound represented by the chemical formula 1-3b, X1 may be O and X2 may be S.

[0220] In one embodiment of the present invention, in the heterocyclic compound represented by the above chemical formula 1-3c, X1 may be S and X2 may be O.

[0221] In one embodiment of the present invention, in the heterocyclic compound represented by the chemical formula 1-3d, X1 may be S and X2 may be S.

[0222]

[0223] In one embodiment of the present invention, the heterocyclic compound represented by the chemical formula 1-4 may be a heterocyclic compound represented by any one of the following chemical formulas 1-4a to 1-4d.

[0224] [Chemical Formula 1-4a]

[0225]

[0226] [Chemical Formula 1-4b]

[0227]

[0228] [Chemical Formula 1-4c]

[0229]

[0230] [Chemical Formula 1-4d]

[0231]

[0232] In the above chemical formulas 1-4a to 1-4d,

[0233] The above X1, X2, R3, R5 and b are the same as the definitions in the above chemical formula 1,

[0234] The above L1 to L3, c to e, Ar1 and Ar2 are the same as the definitions in the above chemical formula 2,

[0235] The above L4, f and Ar3 are the same as the definitions of the above chemical formula 3,

[0236] The above R12 and h are the same as defined in the above chemical formula 1-4.

[0237]

[0238] In one embodiment of the present invention, in the heterocyclic compound represented by the chemical formula 1-4a, X1 may be O and X2 may be O.

[0239] In one embodiment of the present invention, in the heterocyclic compound represented by the chemical formula 1-4b, X1 may be O and X2 may be S.

[0240] In one embodiment of the present invention, in the heterocyclic compound represented by the chemical formula 1-4c, X1 may be S and X2 may be O.

[0241] In one embodiment of the present invention, in the heterocyclic compound represented by the chemical formula 1-4d, X1 may be S and X2 may be S.

[0242]

[0243] In one embodiment of the present invention, all of R1 to R3, R5, R6, R11, R12, Ar1 to Ar3, and L1 to L4 may include non-deuterated hydrogen (H).

[0244] In another embodiment of the present invention, at least one of R1 to R3, R5, R6, R11, R12, Ar1 to Ar3, and L1 to L4 comprises deuterium (D), and at least one of R1 to R3, R5, R6, R11, R12, Ar1 to Ar3, and L1 to L4 may comprise non-deuterated hydrogen.

[0245] In another embodiment of the present invention, R1 to R3, R5, R6, R11, R12, Ar1 to Ar3, and L1 to L4 may all contain deuterium.

[0246]

[0247] 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.

[0248] In another embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 1 may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 1% to 100%.

[0249] In another embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 1 may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 20% to 90%.

[0250] In another embodiment of the present invention, the heterocyclic compound represented by the above chemical formula 1 may not contain deuterium as a substituent, or the content of deuterium with respect to the total number of hydrogen atoms and deuterium atoms may be 30% to 80%.

[0251] 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%.

[0252]

[0253] 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.

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271] In addition, by introducing various substituents into the structure of the above chemical formula 1, compounds having unique characteristics of the introduced substituents can be synthesized. For example, by introducing substituents mainly used in hole injection layer materials, hole transport layer materials, light-emitting layer materials, electron transport layer materials, electron blocking layer materials, and charge generation layer materials used in the manufacture of organic light-emitting devices into the core structure, a material satisfying the conditions required for each organic layer can be synthesized.

[0272] In addition, by introducing various substituents into the structure of the above chemical formula 1, it is possible to finely control the energy band gap, while improving the properties at the interface between organic substances and diversifying the uses of the material.

[0273] Meanwhile, the heterocyclic compound exhibits excellent thermal stability due to its high glass transition temperature (Tg). This increased thermal stability is an important factor in providing operating stability to the device.

[0274] 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.

[0275]

[0276] 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”.

[0277]

[0278] In addition, the present invention

[0279] First electrode;

[0280] A second electrode provided opposite to the first electrode; and

[0281] An organic light-emitting device comprising at least one organic layer provided between the first electrode and the second electrode,

[0282] 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.

[0283]

[0284] In one embodiment of the present invention, the first electrode may be an anode, and the second electrode may be a cathode.

[0285] In another embodiment, the first electrode may be a cathode and the second electrode may be an anode.

[0286]

[0287] In one embodiment of the present invention, the organic layer may include at least one selected from the group consisting of an electron injection layer, an electron transport layer, a hole blocking layer, a light-emitting layer, a light-emitting auxiliary layer, an electron blocking layer, a hole transport layer, and a hole injection layer, and at least one layer selected from the group consisting of an electron injection layer, an electron transport layer, a hole blocking layer, a light-emitting layer, a light-emitting auxiliary layer, an electron blocking layer, a hole transport layer, and a hole injection layer may include a heterocyclic compound represented by the above chemical formula 1.

[0288] In another embodiment of the present invention, the organic layer may include an electron injection layer or an electron transport layer, and the electron injection layer or the electron transport layer may include a heterocyclic compound represented by the chemical formula 1.

[0289] In another embodiment of the present invention, the organic layer may include an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer may include a heterocyclic compound represented by the chemical formula 1.

[0290] In another embodiment of the present invention, the organic layer may include an electron blocking layer, a light emitting layer, or a hole transport layer, and the electron blocking layer, light emitting layer, or hole transport layer may include a heterocyclic compound represented by the chemical formula 1.

[0291] In another embodiment of the present invention, the organic layer may include a hole transport layer, and the hole transport layer may include a heterocyclic compound represented by the chemical formula 1. When the heterocyclic compound represented by the chemical formula 1 is used in the hole transport layer, the heterocyclic compound represented by the chemical formula 1 has fast hole mobility and an appropriate HOMO level, so when the heterocyclic compound represented by the chemical formula 1 is used as the hole transport layer, hole transport to the light-emitting layer is facilitated, thereby lowering the driving voltage of the organic light-emitting device and improving the driving efficiency and lifespan.

[0292] In another embodiment of the present invention, the organic layer may include an electron blocking layer, and the electron blocking layer may include a heterocyclic compound represented by the chemical formula 1. Since the heterocyclic compound represented by the chemical formula 1 has a high LUMO level, using the heterocyclic compound represented by the chemical formula 1 as an electron blocking layer can increase the probability that holes and electrons form excitons, and can increase the probability that light is emitted from the light-emitting layer. Therefore, the electron blocking ability is improved, and the holes and electrons achieve a charge balance, so that the driving efficiency and lifespan of the organic light-emitting device can be improved.

[0293] In another embodiment of the present invention, the organic layer may include a light-emitting layer, and the light-emitting layer may include a heterocyclic compound represented by the chemical formula 1.

[0294] In another embodiment of the present invention, 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.

[0295]

[0296] 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.

[0297] 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.

[0298] 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.

[0299]

[0300] 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.

[0301] 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.

[0302] 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.

[0303]

[0304] In one embodiment of the present invention, the organic light-emitting device may further include one or two or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

[0305]

[0306] The specific details of the heterocyclic compound represented by the above chemical formula 1 are the same as described above.

[0307]

[0308] 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.

[0309] 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.

[0310] 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. For example, a light-emitting auxiliary layer may be added (not shown in Fig. 3).

[0311]

[0312] 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.

[0313] 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.

[0314] 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 an electron injection layer, an electron transport layer, a hole blocking layer, a light-emitting layer, a light-emitting auxiliary layer, an electron blocking layer, a hole transport layer, and a hole injection layer 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.

[0315]

[0316] In addition, the present invention provides a composition for an organic layer of an organic light-emitting device comprising a heterocyclic compound represented by the above chemical formula 1.

[0317] The specific details of the heterocyclic compound represented by the above chemical formula 1 are the same as described above.

[0318] The composition for the organic layer of the above organic light-emitting device can be used when forming the organic layer of the organic light-emitting device, and in particular, can be more preferably used when forming a hole transport layer, an electron blocking layer, a light-emitting layer, or a light-emitting auxiliary layer.

[0319]

[0320] In one embodiment of the present invention, the organic layer includes a heterocyclic compound represented by the chemical formula 1 and can be used together with a phosphorescent dopant.

[0321] 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.

[0322] The above M can be iridium, platinum, osmium, etc.

[0323] 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.

[0324] Specific examples of the above phosphorescent dopants are shown below, but are not limited to these examples.

[0325]

[0326] In one embodiment of the present invention, the organic layer includes a heterocyclic compound represented by the chemical formula 1, and can be used together with an iridium-based dopant.

[0327]

[0328] In one embodiment of the present invention, the iridium-based dopant may be (piq)2(Ir)(acac) as a red phosphorescent dopant, FIrpic as a blue phosphorescent dopant, or Ir(ppy)3 as a green phosphorescent dopant.

[0329]

[0330] 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.

[0331]

[0332] The present invention,

[0333] Steps to prepare the substrate;

[0334] A step of forming a first electrode on the substrate;

[0335] A step of forming one or more organic layers on the first electrode; and

[0336] 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 of an organic light-emitting device according to one embodiment of the present invention.

[0337]

[0338] In one embodiment of the present invention, the step of forming the organic layer may be to form the heterocyclic compound represented by the chemical formula 1 using a thermal vacuum deposition method.

[0339] The organic layer including the heterocyclic compound represented by the above chemical formula 1 may additionally include other substances as needed.

[0340]

[0341] 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 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.

[0342]

[0343] 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.

[0344]

[0345] 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.

[0346]

[0347] 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.

[0348]

[0349] 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.

[0350]

[0351] 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.

[0352]

[0353] For example, LiF is typically used as an electron injection layer material in the art, but the present application is not limited thereto.

[0354]

[0355] 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.

[0356]

[0357] 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.

[0358]

[0359] 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.

[0360]

[0361] 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.

[0362]

[0363] 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.

[0364]

[0365] <Manufacturing Example>

[0366] Manufacturing Example 1. Manufacturing of Intermediate 1

[0367]

[0368]

[0369] Manufacturing Example 1-1. Manufacturing of Intermediate 1-2

[0370] Dibenzo[b,d]furan-3-ol (50 g, 0.145 mol, 1 eq) was dissolved in acetic acid (500 mL), and bromine (Br2) (8.19 mL, 0.160 mol, 1.1 eq) was slowly added dropwise at 0°C and stirred for 5 hours.

[0371] Upon completion of the reaction, the solid was washed with methanol and dried. The product was then dissolved in refluxed dichlorobenzene (DCB), and separated using a silica gel column under dichlorobenzene conditions to obtain 35 g (92% yield) of intermediate 1-2.

[0372]

[0373] Manufacturing Example 1-2. Manufacturing of Intermediate 1-1

[0374] Intermediate 1-2 (35 g, 0.133 mol, 1 eq), 2-chloro-6-hydroxy-phenyl boronic acid (25.2 g, 0.146 mol, 1.1 eq), Na2CO3 (28.2 g, 0.266 mol, 2 eq), and Pd(PPh3)4 (7.69 g, 0.007 mol, 0.05 eq) were added to toluene (420 mL), ethanol (105 mL), and distilled water (H2O) (105 mL) and stirred at 130°C for 14 hours.

[0375] After the reaction was completed, the mixture was cooled to room temperature, extracted with ethyl acetate and distilled water, and moisture was removed with MgSO4. Afterwards, the mixture was separated using a silica gel column to obtain 38 g (yield 94%) of intermediate 1-1.

[0376]

[0377] Manufacturing Example 1-3. Manufacturing of Intermediate 1

[0378] Intermediate 1-1 (38 g, 0.122 mol, 1 eq), p-toluenesulfonic acid (PTSA) (20.4 mL, 0.146 mol, 1.2 eq), and toluene (380 mL) were added and stirred at 100°C for 14 hours.

[0379] After the reaction was completed, the mixture was cooled to room temperature, extracted with saturated NaHCO3 aqueous solution, distilled water, and ethyl acetate, and moisture was removed with MgSO4. After separation using a silica gel column, 30 g (84% yield) of intermediate 1 was obtained.

[0380]

[0381] Intermediates were prepared as shown in Table 1 below by the same method as in Manufacturing Example 1, except that intermediate A in Table 1 below was used instead of dibenzo[b,d]furan-3-ol in Manufacturing Example 1, and intermediate B was used instead of 2-chloro-6-hydroxy-phenylboronic acid.

[0382]

[0383]

[0384]

[0385]

[0386]

[0387] Manufacturing Example 2. Preparation of Compound 1

[0388]

[0389]

[0390] Manufacturing Example 2-1. Manufacturing of Compound 1-2

[0391] Intermediate 1 (20 g, 0.068 mol, 1 eq) was dissolved in acetic acid (200 mL), and then bromine (Br2) (4.0 mL, 0.75 mol, 1.1 eq) was slowly added dropwise at 0°C and stirred for 5 hours.

[0392] Upon completion of the reaction, the solid was washed with methanol and dried. The solid was then dissolved in refluxed dichlorobenzene (DCB), and separated using a silica gel column under dichlorobenzene conditions to obtain 20 g (79% yield) of compound 1-2.

[0393]

[0394] Manufacturing Example 2-2. Preparation of Compound 1-1

[0395] Compound 1-2 (20 g, 0.053 mol, 1 eq), 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane (12.1 g, 0.059 mol, 1.1 eq), Na2CO3 (11.4 g, 0.107 mol, 2 eq), and Pd(PPh3)4 (3.11 g, 0.003 mol, 0.05 eq) were added to 1,4-dioxane (240 mL) and distilled water (H2O) (60 mL) and stirred at 130°C for 8 hours.

[0396] After the reaction was completed, the mixture was cooled to room temperature, extracted with methylene chloride and distilled water, and moisture was removed with MgSO4. Afterwards, the mixture was separated using a silica gel column to obtain 15 g (yield 76%) of compound 1-1.

[0397]

[0398] Manufacturing Example 2-3. Preparation of Compound 1

[0399] Compound 1-1 (15 g, 0.041 mol, 1 eq), diphenylamine (7.57 g, 0.045 mol, 1.1 eq), sodium-t-butoxide (NaOt-Bu) (7.82 g, 0.081 mol, 2 eq), Pd2(dba)3 (1.86 g, 0.002 mol, 0.05 eq), and Xphos (0.97 g, 0.002 mol, 0.05 eq) were added to toluene (150 mL) and stirred at 130°C for 2 hours.

[0400] After the reaction was completed, the mixture was cooled to room temperature, extracted with methylene chloride and distilled water, and moisture was removed with MgSO4. Afterwards, the mixture was separated using a silica gel column to obtain 17 g (83% yield) of compound 1.

[0401]

[0402] Except that in Manufacturing Example 2, the intermediate shown in Table 2 was used instead of Intermediate 1, Compound A was used instead of 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane, and Compound B was used instead of diphenylamine, the target compound was prepared in the same manner as Manufacturing Example 2, as shown in Table 2 below.

[0403]

[0404]

[0405]

[0406]

[0407]

[0408] Manufacturing Example 3. Preparation of Compound 35

[0409]

[0410]

[0411] Manufacturing Example 3-1. Preparation of Compound 35-3

[0412] Intermediate 3 (20 g, 0.064 mol, 1 eq) was dissolved in acetic acid (200 mL), and then bromine (Br2) (3.8 mL, 0.071 mol, 1.1 eq) was slowly added dropwise at 0°C and stirred for 5 hours.

[0413] Upon completion of the reaction, the solid was washed with methanol and dried. The resulting product was dissolved in refluxed dichlorobenzene (DCB), and separated using a silica gel column under dichlorobenzene conditions to obtain 22 g (87% yield) of compound 35-3.

[0414]

[0415] Manufacturing Example 3-2. Preparation of Compound 35-2

[0416] Compound 35-3 (22 g, 0.053 mol, 1 eq), 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane (12.7 g, 0.062 mol, 1.1 eq), Na2CO3 (12.03 g, 0.113 mol, 2 eq), and Pd(PPh3)4 (3.28 g, 0.003 mol, 0.05 eq) were added to 1,4-dioxane (264 mL) and distilled water (H2O) (66 mL) and stirred at 130°C for 8 hours.

[0417] After the reaction was completed, the mixture was cooled to room temperature, extracted with methylene chloride and distilled water, and moisture was removed with MgSO4. Afterwards, the mixture was separated using a silica gel column to obtain 16 g (yield 73%) of compound 35-2.

[0418]

[0419] Manufacturing Example 3-3. Preparation of Compound 35-1

[0420] Add compound 35-2 (16 g, 0.041 mol, 1 eq), 2-(4-bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (12.94 g, 0.046 mol, 1.1 eq), K2CO3 (11.49 g, 0.083 mol, 2 eq), Pd2(dba)3 (1.90 g, 0.002 mol, 0.05 eq), Xphos (0.99 g, 0.002 mol, 0.05 eq) to 1,4-dioxane (192 mL) and distilled water (H2O) (48 mL). Stirred at 130℃ for 8 hours.

[0421] After the reaction was completed, the mixture was cooled to room temperature, extracted with methylene chloride and distilled water, and moisture was removed with MgSO4. Afterwards, the mixture was separated using a silica gel column to obtain 19 g (yield 90%) of compound 35-1.

[0422]

[0423] Manufacturing Example 3-4. Preparation of Compound 35

[0424] Compound 35-1 (19 g, 0.037 mol, 1 eq), N-phenyl-[1,1'-biphenyl]-4-amine (10.22 g, 0.041 mol, 1.1 eq), sodium-t-butoxide (NaOt-Bu) (7.23 g, 0.075 mol, 2 eq), Pd2(dba)3 (1.72 g, 0.002 mol, 0.05 eq), and Xphos (0.90 g, 0.002 mol, 0.05 eq) were added to toluene (190 mL) and stirred at 130°C for 2 hours.

[0425] After the reaction was completed, the mixture was cooled to room temperature, extracted with methylene chloride and distilled water, and moisture was removed with MgSO4. After separation using a silica gel column, 19 g (yield 75%) of compound 35 was obtained.

[0426]

[0427] Except that in Manufacturing Example 3, the intermediate shown in Table 3 was used instead of Intermediate 3, Compound C was used instead of 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane, and Compound D was used instead of N-phenyl-[1,1'-biphenyl]-4-amine, the target compound was prepared in the same manner as Manufacturing Example 3, as shown in Table 3 below.

[0428]

[0429]

[0430]

[0431]

[0432]

[0433] Manufacturing Example 4. Preparation of Compound 69

[0434]

[0435]

[0436] Manufacturing Example 4-1. Preparation of Compound 69-2

[0437] Intermediate 5 (20 g, 0.059 mol, 1 eq), 4,4,5,5-tetramethyl-2-naphthalen-1-yl-1,3,2-dioxaborolane (16.58 g, 0.065 mol, 1.1 eq), Na2CO3 (12.57 g, 0.118 mol, 2 eq), and Pd(PPh3)4 (3.43 g, 0.003 mol, 0.05 eq) were added to 1,4-dioxane (240 mL) and distilled water (H2O) (60 mL) and stirred at 130°C for 8 hours.

[0438] After the reaction was completed, the mixture was cooled to room temperature, extracted with methylene chloride and distilled water, and moisture was removed with MgSO4. Afterwards, the mixture was separated using a silica gel column to obtain 19 g (yield 83%) of compound 69-2.

[0439]

[0440] Manufacturing Example 4-2. Preparation of Compound 69-1

[0441] Compound 69-2 (19 g, 0.049 mol, 1 eq) was dissolved in acetic acid (190 mL), and bromine (Br2) (2.9 mL, 0.054 mol, 1.1 eq) was slowly added dropwise at 0°C and stirred for 5 hours.

[0442] Upon completion of the reaction, the solid was washed with methanol and dried. It was then dissolved in refluxed dichlorobenzene (DCB), and separated using a silica gel column under dichlorobenzene conditions to obtain 17 g (yield 74%) of compound 69-1.

[0443]

[0444] Manufacturing Example 4-3. Preparation of Compound 69

[0445] Compound 69-1 (17 g, 0.037 mol, 1 eq), diphenylamine (6.83 g, 0.040 mol, 1.1 eq), sodium-t-butoxide (NaOt-Bu) (7.05 g, 0.073 mol, 2 eq), Pd2(dba)3 (1.68 g, 0.002 mol, 0.05 eq), and Xphos (0.87 g, 0.002 mol, 0.05 eq) were added to toluene (170 mL) and stirred at 130°C for 2 hours.

[0446] After the reaction was completed, the mixture was cooled to room temperature, extracted with methylene chloride and distilled water, and moisture was removed with MgSO4. After separation using a silica gel column, 13 g (yield 64%) of compound 69 was obtained.

[0447]

[0448] Except that the intermediate in Table 4 below was used instead of intermediate 5 in Manufacturing Example 4, compound E was used instead of 4,4,5,5-tetramethyl-2-naphthalen-1yl-1,3,2-dioxaborolane, and compound F was used instead of diphenylamine, the target compound was prepared in the same manner as Manufacturing Example 4, as shown in Table 4 below.

[0449]

[0450]

[0451]

[0452]

[0453]

[0454] Manufacturing Example 5. Preparation of Compound 89

[0455]

[0456]

[0457] Manufacturing Example 5-1. Manufacturing of Compound 89-3

[0458] Intermediate 5 (20 g, 0.059 mol, 1 eq), 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane (13.32 g, 0.065 mol, 1.1 eq), Na2CO3 (12.57 g, 0.118 mol, 2 eq), and Pd(PPh3)4 (3.43 g, 0.003 mol, 0.05 eq) were added to 1,4-dioxane (240 mL) and distilled water (H2O) (60 mL) and stirred at 130°C for 8 hours.

[0459] After the reaction was completed, the mixture was cooled to room temperature, extracted with methylene chloride and distilled water, and moisture was removed with MgSO4. Afterwards, the mixture was separated using a silica gel column to obtain 16 g (yield 80%) of compound 89-3.

[0460]

[0461] Manufacturing Example 5-2. Preparation of Compound 89-2

[0462] Compound 89-3 (16 g, 0.032 mol, 1 eq) was dissolved in acetic acid (160 mL), and bromine (Br2) (1.9 mL, 0.035 mol, 1.1 eq) was slowly added dropwise at 0°C and stirred for 5 hours.

[0463] Upon completion of the reaction, the solid was washed with methanol and dried. The resulting product was dissolved in refluxed dichlorobenzene (DCB), and separated using a silica gel column under dichlorobenzene conditions to obtain 11 g (82% yield) of compound 89-2.

[0464]

[0465] Manufacturing Example 5-3. Preparation of Compound 89-1

[0466] Compound 89-2 (11 g, 0.027 mol, 1 eq), 2-(4-bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (8.29 g, 0.029 mol, 1.1 eq), K2CO3 (7.36 g, 0.053 mol, 2 eq), Pd2(dba)3 (1.22 g, 0.001 mol, 0.05 eq) and Xphos (0.63 g, 0.001 mol, 0.05 eq) were added to 1,4-dioxane (132 mL) and distilled water (H2O) (33 mL). Stirred at 130℃ for 8 hours.

[0467] After the reaction was completed, the mixture was cooled to room temperature, extracted with methylene chloride and distilled water, and moisture was removed with MgSO4. After separation using a silica gel column, 12 g (yield 92%) of compound 89-1 was obtained.

[0468]

[0469] Manufacturing Example 5-4. Preparation of Compound 89

[0470] Compound 89-1 (12 g, 0.025 mol, 1 eq), N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]thiophen-4-amine (10.56 g, 0.027 mol, 1.1 eq), sodium-t-butoxide (NaOt-Bu) (4.71 g, 0.049 mol, 2 eq), Pd2(dba)3 (1.12 g, 0.001 mol, 0.05 eq) and Xphos (0.58 g, 0.001 mol, 0.05 eq) were added to toluene (120 mL) and stirred at 130°C for 2 hours. Stirred.

[0471] After the reaction was completed, the mixture was cooled to room temperature, extracted with methylene chloride and distilled water, and moisture was removed with MgSO4. After separation using a silica gel column, 16 g (yield 82%) of compound 89 was obtained.

[0472]

[0473] Except that the intermediate of Table 5 was used instead of Intermediate 5 in the above Manufacturing Example 5, Compound G was used instead of 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane, and Compound H was used instead of N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]thiophene-4-amine, the target compound was prepared in the same manner as Manufacturing Example 5, as shown in Table 5 below.

[0474]

[0475]

[0476]

[0477]

[0478]

[0479] Manufacturing Example 6. Preparation of Compound 273

[0480]

[0481] Compound 1 (10 g, 0.020 mol, 1 eq), D6-benzene (100 mL), and triflic acid (TfOH) (12.32 mL, 0.651 mol, 7.0 eq) were added and stirred at 60°C for 3 hours. Water was added to terminate the reaction, and the mixture was extracted with methylene chloride and water, and moisture was removed with MgSO4. After separation using a silica gel column, 9 g (86% yield) of compound 273 was obtained.

[0482]

[0483] In the above Manufacturing Example 6, the compound of Table 6 below was used instead of compound 1, and the reaction time and the equivalent amount of triflic acid were used as in Table 6 below, and the compound was manufactured in the same manner as in Manufacturing Example 6, as in Table 6 below.

[0484]

[0485]

[0486]

[0487]

[0488]

[0489]

[0490]

[0491]

[0492]

[0493]

[0494]

[0495]

[0496]

[0497]

[0498]

[0499]

[0500] The results of the synthesis of the compounds described in Manufacturing Examples 1 to 6 and Tables 1 to 6 are shown in Tables 7 and 8 below.

[0501] Table 7 below 1 The values ​​are measured by H NMR (CDCl3, 400 MHz), and Table 8 below is measured by FD-mass spectrometry (FD-MS: Field desorption mass spectrometry).

[0502]

[0503]

[0504]

[0505]

[0506]

[0507] Compound FD-MS Compound FD-MS 1 m / z = 501.17 (C 36 H 23 NO2=501.59)3m / z= 719.23 (C 52 H 33 NOS=719.90)9m / z= 839.29 (C 60 H 41 NO2S=840.05)22m / z= 905.24 (C 63 H 39 NO2S2=906.13)24m / z= 785.22 (C 56 H 35 NS2=786.02)27m / z= 809.28 (C 59 H 39 NOS=810.03)35m / z=669.21 (C 48 H 31 NOS=669.84)49m / z=885.27 (C 64 H 39 NO2S=886.08)51m / z=815.23 (C 57 H 37 NOS2=816.05)64m / z=887.27 (C 64 H 41NS2=888.16)65m / z=955.35 (C 72 H 45 NO2=956.16)68m / z=811.24 (C 58 H 37 NS2=812.06)69m / z=551.19 (C 40 H 25 NO2=551.65)75m / z=809.24 (C 58 H 35 NO2S=809.98)77m / z=783.31 (C 58 H 41 NO2=783.97)89m / z=799.25 (C 57 H 37 NO2S=799.99)94m / z=809.28 (C 59 H 39 NOS=810.03)101m / z=899.33 (C 67 H 34 NO2=894.09)103m / z=719.23 (C 52 H 33 NOS=719.90)110m / z=759.22 (C 54 H 33 NO2S=759.92)118m / z=799.25 (C 57 H 37 NO2S=799.99)123m / z=845.28 (C 62 H 39 NOS=846.06)132m / z=977.28 (C 70 H 43 NOS2=978.24)134m / z=921.31 (C 68 H 43 NOS=922.16)137m / z=607.16 (C 42 H 25 NO2S=607.73)139m / z=719.23 (C 52 H 33 NOS=719.90)146m / z=719.23 (C 52 H 33 NOS=719.90)158m / z=981.27 (C 69 H 43 NO2S2=982.23)161m / z=793.26 (C58 H 35 NO3=793.92)170m / z=683.19 (C 48 H 29 NO2S=683.83)177m / z=859.35 (C 64 H 45 NO2=860.07)180m / z=775.20 (C 54 H 33 NOS2=775.98)187m / z=921.22 (C 63 H 39 NOS3=922.19)190m / z=845.28 (C 62 H 39 NOS=846.06)197m / z=1017.36 (C 77 H 47 NO2=1018.23)203m / z=1011.32 (C 74 H 45 NO2S=1012.24)205m / z=501.17 (C 36 H 23 NO2=501.59)214m / z=769.24 (C 56 H 35 NOS=769.96)218m / z=733.21 (C 52 H 31 NO2S=733.89)230m / z=759.26 (C 55 H 37 NOS=759.97)235m / z=959.32 (C 71 H 45 NOS=960.21)238m / z=593.18 (C 42 H 27 NOS=593.74)241m / z=835.25 (C 60 H 37 NO2S=836.02)243m / z=835.29 (C 61 H 41 NOS=836.06)248m / z=825.22 (C 58 H 35 NOS2=826.04)258m / z=901.25 (C 64 H 39 NOS2=902.14)268m / z=937.28 (C 68 H43 NS2=938.22)271m / z=921.31 (C 68 H 43 NOS=922.16)273m / z=524.32 (C 36 D 23 NO2=524.73)274m / z=752.44 (C 52 D 33 NOS=753.10)275m / z=865.45 (C 60 H 15 D 26 NO2=866.21)276m / z=916.54 (C 63 D 41 NO2S=917.34)277m / z=820.44 (C 56 D 35 NS2=821.24)278m / z=848.52 (C 59 D 39 NOS=849.26)279m / z=700.41 (C 48 D 31 NOS=701.03)280m / z=924.51 (C 64 D 39 NO2S=925.32)281m / z=852.46 (C 57 D 37 NOS2=853.27)282m / z=928.53 (C 64 D 41 NS2=929.41)283m / z=994.59 (C 72 H6D 39 NO2=995.39)284m / z=848.47 (C 58 D 37 NS2=849.29)285m / z=576.35 (C 40 D 25 NO2=576.80)286m / z=844.46 (C 58 D 35 NO2S=845.20))287m / z=824.57 (C 58 D 41 NO2=825.22)288m / z=836.49 (C 57 D 37 NO2S=837.21)289m / z=848.52 (C 59 D39 NOS=849.26)290m / z=930.56 (C 67 H6D 37 NO2=931.31)291m / z=752.44 (C 52 D 33 NOS=753.10)292m / z=792.43 (C 54 D 33 NO2S=793.12)293m / z=836.49 (C 57 D 37 NO2S=837.21)294m / z=884.52 (C 62 D 39 NOS=885.30)295m / z=1020.55 (C 70 D 43 NOS2=1021.50)296m / z=964.58 (C 68 D 43 NOS=965.42)297m / z=632.32 (C 42 D 25 NO2S=632.88)298m / z=752.44 (C 52 D 33 NOS=753.10)299m / z=752.44 (C 52 D 33 NOS=753.10)300m / z=1013.47(C 69 H 11 D 32 NO2S2=1014.42)301m / z=828.48 (C 58 D 35 NO3=829.14)302m / z=712.37 (C 48 D 29 NO2S=713.00)303m / z=904.63 (C 64 D 45 NO2=905.34)304m / z=808.41 (C 54 D 33 NOS2=809.19)305m / z=960.46 (C 63 D 39 NOS3=961.43)306m / z=884.52 (C 63 D 39 NOS=885.30)307m / z=1064.66 (C 77 D47 NO2=1065.51)308m / z=1056.60 (C 74 D 45 NO2S=1057.51)309m / z=524.32 (C 36 D 23 NO2=524.73)310m / z=804.46 (C 56 D 35 NOS=805.18)311m / z=764.40 (C 52 D 31 NO2S=765.07)312m / z=796.49 (C 55 D 37 NOS=797.19)313m / z=1004.60 (C 71 D 45 NOS=1005.48)314m / z=620.35 (C 42 D 27 NOS=620.91)315m / z=872.49 (C 60 D 37 NO2S=873.25)316m / z=912.57 (C 64 D 41 NO3=913.29)317m / z=964.51 (C 66 D 39 NO3S=965.34)318m / z=940.49 (C 64 D 39 NOS2=941.38)319m / z=1130.57(C 79 H 10 D 39 NOS2=1131.62)320m / z=1000.63 (C 72 D 45 NO2=1001.43)

[0508]

[0509] Experimental Example 1.

[0510] Experimental Example 1-1. Fabrication of an Organic Light-Emitting Device

[0511] A transparent electrode ITO thin film obtained from OLED glass (manufactured by Samsung Corning) was ultrasonically cleaned sequentially in trichloroethylene, acetone, ethanol, and distilled water for 5 minutes each, and then stored in isopropanol before use. Next, the ITO substrate was installed in the substrate folder of a vacuum deposition device.

[0512] 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenyl amine (4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenyl amine: 2-TNATA) was placed in a cell within a vacuum deposition device.

[0513]

[0514] Then the vacuum level inside the chamber is 10 -6 After exhausting to reach 10 torr, a current was applied to the cell to evaporate 2-TNATA, thereby depositing a 600 Å thick hole injection layer on an ITO substrate. In another cell within a vacuum deposition device, a heterocyclic compound represented by Chemical Formula 1 or a comparative compound as described in Table 9 below was placed, and a current was applied to the cell to evaporate it, thereby depositing a 300 Å thick hole transport layer on the hole injection layer.

[0515]

[0516] After forming the hole injection layer and the hole transport layer as described above, a blue light-emitting material having the following structure was deposited thereon as a light-emitting layer. Specifically, a blue light-emitting host material, H1, was vacuum-deposited to a thickness of 200 Å in one cell within a vacuum deposition device, and a blue light-emitting dopant material, D1, was vacuum-deposited thereon at a thickness of 5% relative to the host material. Thereafter, E1 was deposited to a thickness of 300 Å as an electron transport layer.

[0517]

[0518] Afterwards, lithium fluoride (LiF) was deposited with a thickness of 10 Å as an electron injection layer, and Al was deposited with a thickness of 1000 Å to form a cathode, thereby fabricating an organic light-emitting device.

[0519] Meanwhile, all organic compounds required for the production of organic light-emitting devices are 10 for each material. -6 ~10 -8 It was purified by vacuum sublimation under 10 torr and used in the production of organic light-emitting devices.

[0520]

[0521] Experimental Example 1-2. Driving Voltage and Luminous Efficiency of Organic Light-Emitting Devices

[0522] The electroluminescence (EL) characteristics of the organic electroluminescent device manufactured as described above were measured using M7000 from Max Science, and the standard luminance was determined to be 700 cd / m using the lifespan measurement equipment (M6000) manufactured by Max Science based on the measurement results. 2 The lifespan T is the time it takes for the initial luminance to reach 95% of its original brightness. 95 was measured.

[0523] The driving voltage, luminous efficiency and lifespan (T) of the blue organic light-emitting device manufactured according to the above manufacturing method 95 ) are measured as shown in Table 9.

[0524]

[0525] Compound Driving voltage (V) Luminous efficacy (cd / A) CIE (x, y) Lifetime (T95) Comparative example 1 NPB 5.48 6.03 (0.134, 0.100) 60 Comparative example 2 Comparative compound A 5.44 6.13 (0.135, 0.101) 63 Comparative example 3 Comparative compound B 5.75 6.22 (0.134, 0.101) 68 Comparative example 4 Comparative compound C 5.41 6.23 (0.132, 0.101) 67 Comparative example 5 Comparative compound D 5.39 6.20 (0.131, 0.100) 65 Comparative example 6 Comparative compound E 5.43 6.22 (0.133, 0.100) 70 Comparative example 7Comparative compound F5.426.21(0.132, 0.101)73Comparative example 8Comparative compound G5.446.21(0.133, 0.101)71Comparative example 9Comparative compound H5.246.25(0.132, 0.101)73Example 114.866.95(0.134, 0.100)90Example 234.837.05(0.133, 0.101)93Example 394.896.99(0.134, 0.101)95Example 4224.856.95(0.133, 0.100)91Example 5244.847.03(0.132, 0.101)93 Example 6274.836.92(0.133, 0.100)92 Example 7354.846.95(0.134, 0.100)93 Example 8494.806.89(0.133, 0.102)95 Example 9514.786.93(0.134, 0.101)94 Example 10644.837.00(0.133, 0.100)91 Example 11654.856.90(0.132, 0.101)90 Example 12684.886.93(0.134, 0.100)92 Example 13694.826.95(0.132, 0.102)95 Example 14754.896.91(0.133, 0.100)92 Example 15774.816.88(0.133, 0.100)90 Example 16894.856.93(0.134, 0.101)94 Example 17944.826.98(0.133, 0.101)93 Example 181014.896.93(0.132, 0.101)91 Example 191034.916.98(0.132, 0.102)91 Example 201104.817.04(0.132, 0.100)93 Example 211184.846.89(0.133, 0.100)90 Example 221234.896.99(0.133, 0.101)91 Example 231324.846.97(0.134, 0.100)93 Example 241344.876.96(0.133, 0.100)92 Example 252734.816.88(0.132, 0.102)101 Example 262744.836.93(0.134, 0.101)113 Example 272754.826.95(0.134, 0.102)110 Example 282764.947.03(0.133, 0.100)108 Example 29 2774.89 6.97 (0.133, 0.100)99 Example 30 2784.85 6.92 (0.134, 0.101)100 Example 31 2794.84 6.91 (0.133, 0.100)101 Example 32 2804.87 6.76 (0.133, 0.101)109 Example 33 2814.90 6.85 (0.134, 0.100)113 Example 34 2824.81 6.82 (0.133, 0.100)110 Example 35 2834.83 6.88 (0.134, 0.100)107 Example 36 2844.916.90 (0.133, 0.101)103 Example 37 2854.886.79 (0.133, 0.100)101 Example 38 2864.846.77 (0.133, 0.101)110 Example 39 2874.846.81 (0.133, 0.100)115 Example 40 2884.916.88 (0.134, 0.100)113 Example 41 2894.906.88 (0.133, 0.100)100 Example 42 2904.826.86 (0.133, 0.100)99 Example 43 2914.84 6.81 (0.133, 0.100)98 Example 44 2924.81 6.86 (0.133, 0.100)101 Example 45 2934.88 6.84 (0.133, 0.101)105 Example 46 2944.84 6.86 (0.134, 0.101)103 Example 47 2954.84 6.90 (0.133, 0.100)107 Example 48 2964.83 6.90 (0.133, 0.101)99.

[0526]

[0527] [Comparative Compound]

[0528]

[0529] As shown in the results in Table 9 above, the blue organic light-emitting devices of Examples 1 to 48 using the heterocyclic compound represented by Chemical Formula 1 of the present invention as a hole transport layer showed lower driving voltage and significantly superior luminous efficiency and lifespan compared to Comparative Examples 1 to 9. Comparative Examples 2 to 5 showed higher driving voltage and higher luminous efficiency and lifespan than the compound of the present invention when applied to an organic light-emitting device due to the poor hole transport effect due to the structure of the compound. In addition, Comparative Examples 2 to 5 did not include Chemical Formula 2 and Chemical Formula 3 as substituents. Due to these structural features, it can be seen that the organic light-emitting device including the heterocyclic compound represented by Chemical Formula 1 of the present invention as a hole transport layer has lower driving voltage and superior luminous efficiency and lifespan. Specifically, the heterocyclic compound represented by Chemical Formula 1 of the present invention showed increased stability as the HOMO orbital was widely expanded to the substituent skeleton of Chemical Formula 2 and Chemical Formula 3, thereby improving the lifespan when applied to a device.

[0530] Comparative Examples 6 to 7 have a monosubstituted structure, whereas the heterocyclic compound represented by Chemical Formula 1 of the present invention has a disubstituted structure, i.e., a disubstituted structure, having substituents of Chemical Formula 2 and Chemical Formula 3. With this structural feature, the hole transport property of the compound is improved by having the substitution structures of Chemical Formula 2 and Chemical Formula 3 that have electron donating properties, and when applied to an organic light-emitting device, the probability of recombination of holes and electrons within the light-emitting layer can be improved.

[0531] Comparative Example 8 has a structure in which two substitutions are made in the same direction, which may increase steric hindrance. When steric hindrance increases, hole mobility decreases, which increases the driving voltage, and the charge balance is not correct, which reduces efficiency and deteriorates due to electron accumulation, which reduces the lifespan. In addition, the heterocyclic compound represented by Chemical Formula 1 of the present invention exhibits suitable mobility when applied to organic light-emitting devices due to its linear structure, but Comparative Example 8 did not exhibit suitable mobility.

[0532] Comparative Example 9 is a compound used as a host, and has a different type of substituent than the heterocyclic compound represented by Chemical Formula 1 of the present invention. Comparative Example 9 exhibited a lower hole transport effect, and when applied to an organic light-emitting device, the driving voltage was higher, and the luminous efficiency and lifespan were higher than those of the heterocyclic compound represented by Chemical Formula 1 of the present invention.

[0533]

[0534] Experimental example 2.

[0535] Experimental Example 2-1. Fabrication of an Organic Light-Emitting Device

[0536] A transparent electrode ITO thin film obtained from glass for OLED (manufactured by Samsung Corning) was ultrasonically cleaned sequentially using trichloroethylene, acetone, ethanol, and distilled water for 5 minutes each, and then stored in isopropanol before use.

[0537] An ITO substrate was installed in the substrate folder of a vacuum deposition equipment, and 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenyl amine (4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenyl amine: 2-TNATA) was added.

[0538]

[0539] Then the vacuum level inside the chamber is 10 -6After evacuating to 10 torr, a current was applied to the cell to evaporate 2-TNATA, depositing a 600 Å thick hole injection layer on an ITO substrate. N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) was placed in another cell within the vacuum deposition equipment, and a current was applied to the cell to evaporate it, depositing a 250 Å thick hole transport layer on the hole injection layer.

[0540]

[0541] Next, a heterocyclic compound represented by Chemical Formula 1 or a comparative compound described in Table 10 was deposited as an electron blocking layer to a thickness of 50 Å.

[0542] On top of that, a blue light-emitting material having the following structure was deposited as a light-emitting layer. Specifically, a blue light-emitting host material, H1, was vacuum-deposited to a thickness of 200 Å in one cell within a vacuum deposition device, and a blue light-emitting dopant material, D1, was vacuum-deposited thereon at 5% of the host material.

[0543]

[0544] Afterwards, a compound of the following structural formula E1 was deposited as an electron transport layer with a thickness of 300 Å.

[0545]

[0546] Afterwards, lithium fluoride (LiF) was deposited with a thickness of 10 Å as an electron injection layer, and Al was deposited with a thickness of 1000 Å to form a cathode, thereby fabricating an organic light-emitting device.

[0547] Meanwhile, all organic compounds required for the production of organic light-emitting devices are 10 for each material. -6 ~10 -8 It was purified by vacuum sublimation under 10 torr and used in the production of organic light-emitting devices.

[0548]

[0549] Experimental Example 2-2. Driving Voltage and Luminous Efficiency of Organic Light-Emitting Devices

[0550] The electroluminescence (EL) characteristics of the organic electroluminescent device manufactured as described above were measured using M7000 from Max Science, and the standard luminance was determined to be 700 cd / m using the lifespan measurement equipment (M6000) manufactured by Max Science based on the measurement results. 2 The lifespan T is the time it takes for the initial luminance to reach 95% of its original brightness. 95 was measured.

[0551] The driving voltage, luminous efficiency and lifespan (T) of the green organic light-emitting device manufactured according to the above manufacturing method 95 ) are measured as shown in Table 10.

[0552]

[0553] Compound Driving voltage (V) Luminous efficacy (cd / A) CIE (x, y) Lifetime (T95) Comparative example 10 NPB 5.55 6.07 (0.134, 0.100) 53 Comparative example 11 Comparative compound A 5.42 6.13 (0.134, 0.100) 52 Comparative example 12 Comparative compound B 5.33 6.11 (0.133, 0.100) 54 Comparative example 13 Comparative compound C 5.31 6.18 (0.133, 0.100) 59 Comparative example 14 Comparative compound D 5.30 6.15 (0.132, 0.101) 58 Comparative example 15 Comparative compound E 5.32 6.20 (0.134, 0.100)60Comparative Example 16Comparative Compound F5.316.21(0.133, 0.101)61Comparative Example 17Comparative Compound G5.326.19(0.134, 0.101)58Comparative Example 18Comparative Compound H5.346.23(0.134, 0.100)61Example 491374.736.89(0.133, 0.100)90Example 501394.706.85(0.133, 0.101)89Example 511464.657.04(0.134, 0.100)88Example 521584.706.90(0.134, 0.100)94 Example 53 1614.78 6.94 (0.133, 0.101)89 Example 54 1704.80 7.01 (0.134, 0.101)88 Example 55 1774.82 6.93 (0.133, 0.100)90 Example 56 1804.75 6.89 (0.134, 0.101)87 Example 57 1874.71 6.98 (0.133, 0.101)95 Example 58 1904.78 6.88 (0.134, 0.100)89 Example 59 1974.80 6.94 (0.133, 0.100)90 Example 602034.706.79(0.134, 0.100)90 Example 612054.807.01(0.133, 0.100)95 Example 622144.786.94(0.133, 0.101)88 Example 632184.776.99(0.134, 0.101)87 Example 642304.837.03(0.134, 0.100)94 Example 652354.756.97(0.134, 0.100)99 Example 662384.767.00(0.133, 0.101)87 Example 672414.736.88(0.134, 0.100)87 Example 682434.736.89(0.133, 0.100)94 Example 692484.766.83(0.134, 0.100)86 Example 702584.786.90(0.133, 0.100)86 Example 712684.756.94(0.133, 0.100)86 Example 722714.786.95(0.134, 0.100)88 Example 732974.797.00(0.133, 0.101)99 Example 742984.807.01(0.133, 0.100)101 Example 752994.796.97(0.134, 0.100)103 Example 76 3004.807.05(0.134, 0.100)99 Example 77 3014.756.85(0.134, 0.100)102 Example 78 3024.776.89(0.133, 0.100)106 Example 79 3034.856.85(0.133, 0.100)110 Example 80 3044.886.83(0.134, 0.102)107 Example 81 3054.866.86(0.133, 0.102)99 Example 82 3064.856.88(0.133, 0.101)100 Example 833074.846.85(0.134, 0.100)101 Example 843084.816.81(0.134, 0.100)105 Example 853094.806.90(0.133, 0.101)107 Example 863104.846.83(0.133, 0.100)103 Example 873114.796.86(0.133, 0.100)109 Example 883124.806.90(0.133, 0.101)112 Example 893134.836.88(0.134, 0.101)101 Example 903144.856.87(0.133, 0.100)99 Example 913154.866.87(0.133, 0.100)114 Example 923164.816.87(0.133, 0.101)102 Example 933174.856.91(0.134, 0.100)107 Example 943184.866.83(0.133, 0.101)102 Example 953194.886.84(0.134, 0.100)99 Example 963204.846.86(0.133, 0.101)115.

[0554]

[0555] [Comparative Compound]

[0556]

[0557]

[0558] In the results of Table 10 above, the blue organic light-emitting devices of Examples 49 to 96 using the heterocyclic compound represented by Chemical Formula 1 of the present invention as an electron blocking layer showed lower driving voltage and significantly superior luminous efficiency and lifespan compared to Comparative Examples 10 to 18.

[0559] The heterocyclic compound represented by the chemical formula 1 of the present invention has the advantage of being able to implement a higher T1 level and being able to control the LUMO level to a level more suitable as an electron blocking layer by the substituents of the chemical formulas 2 and 3 used.

[0560] Comparative Examples 11, 12 and 15, 16 have a single-substitution structure, making it difficult to form various types of structures, making it difficult to control the physical properties suitable for an electron-blocking layer. Comparative Examples 13 and 14 are compounds in which a triazine group is used as a substituent, and the substituent is rich in electrons rather than holes, resulting in poor device properties as an electron-blocking layer. Comparative Example 17 has two substituents oriented in the same direction, and as the molecular structure of the substituent increases, steric hindrance increases. As steric hindrance increases, hole mobility decreases, which has the disadvantage of high driving voltage, low luminous efficiency, and low lifespan. Comparative Example 18 has a structure of a compound used as a host, resulting in poor device properties as an electron-blocking layer.

[0561] Therefore, the heterocyclic compound represented by the chemical formula 1 of the present invention can exhibit low driving voltage, high efficiency, and high lifespan characteristics.

[0562]

[0563] [Explanation of symbols]

[0564] 100: substrate

[0565] 200: Bipolar

[0566] 300: Organic layer

[0567] 301: Hole injection layer

[0568] 302: Hole transport layer

[0569] 303: Emissive layer

[0570] 304: Hole blocking layer

[0571] 305: Electron transport layer

[0572] 306: Electron injection layer

[0573] 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 the same or different from each other, and are each independently O; or S, wherein R1 to R3, R5 and R6 are the same as or different from each other, and each independently represent hydrogen; deuterium; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; -P(=O)R101R102; -SiR101R102R103; -NR101R102; selected from the group consisting of the following Chemical Formula 2; and the following Chemical Formula 3, or a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring in which two or more adjacent groups bind each other; or forms a substituted or unsubstituted C2 to C60 heterocyclic ring, wherein R101, R102 and R103 are the same as or different from each other, and each independently represents a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, Either one of the above R1 and R6 is the following chemical formula 2; or the following chemical formula 3, The above R4 is the following chemical formula 2; or the following chemical formula 3, The above R1, R4 and R6 are different from each other, The above a is an integer from 0 to 3, and when a is 2 or greater, R2 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, R5 are equal to or different from each other, [Chemical formula 2] [Chemical Formula 3] In the above chemical formulas 2 and 3, The above L1 to L4 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 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 d is an integer from 0 to 5, and when d is 2 or greater, L2 is equal to or less than each other, The above e is an integer from 0 to 5, and when e is 2 or greater, L3 are equal to or different from each other, The above f is an integer from 0 to 5, and when f is 2 or greater, L4 are equal to or different from each other, The above Ar1 to Ar3 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.

2. In paragraph 1, The heterocyclic compound represented by the above chemical formula 1 is a heterocyclic compound represented by any one of the following chemical formulas 1-1 to 1-4: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] In the above chemical formulas 1-1 to 1-4, wherein R11 and R12 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 g is an integer from 0 to 4, and when g is 2 or greater, R11 is equal to or different from each other, The above h is an integer from 0 to 4, and when h is 2 or greater, R12 are equal to or different from each other, The above X1, X2, R2, R3, R5, a and b are the same as the definitions in the above chemical formula 1, The above L1 to L3, c to e, Ar1 and Ar2 are the same as the definitions in the above chemical formula 2, The above L4, f and Ar3 are identical to the definitions in the above chemical formula 3.

3. In paragraph 2, The heterocyclic compound represented by the above chemical formula 1-1 is a heterocyclic compound represented by any one of the following chemical formulas 1-1a to 1-1d: [Chemical Formula 1-1a] [Chemical Formula 1-1b] [Chemical Formula 1-1c] [Chemical Formula 1-1d] In the above chemical formulas 1-1a to 1-1d, The above X1, X2, R2, R3 and a are the same as the definitions in the above chemical formula 1, The above L1 to L3, c to e, Ar1 and Ar2 are the same as the definitions in the above chemical formula 2, The above L4, f and Ar3 are the same as the definitions of the above chemical formula 3, The above R11 and g are the same as defined in the above chemical formula 1-1.

4. In paragraph 2, 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 1-2d: [Chemical Formula 1-2a] [Chemical Formula 1-2b] [Chemical formula 1-2c] [Chemical formula 1-2d] In the above chemical formulas 1-2a to 1-2d, The above X1, X2, R2, R3 and a are the same as the definitions in the above chemical formula 1, The above L1 to L3, c to e, Ar1 and Ar2 are the same as the definitions in the above chemical formula 2, The above L4, f and Ar3 are the same as the definitions of the above chemical formula 3, The above R11 and g are the same as defined in the above chemical formula 1-2.

5. In paragraph 2, The heterocyclic compound represented by the above chemical formula 1-3 is a heterocyclic compound represented by any one of the following chemical formulas 1-3a to 1-3d: [Chemical Formula 1-3a] [Chemical Formula 1-3b] [Chemical formula 1-3c] [Chemical formula 1-3d] In the above chemical formulas 1-3a to 1-3d, The above X1, X2, R3, R5 and b are the same as the definitions in the above chemical formula 1, The above L1 to L3, c to e, Ar1 and Ar2 are the same as the definitions in the above chemical formula 2, The above L4, f and Ar3 are the same as the definitions of the above chemical formula 3, The above R12 and h are the same as defined in the above chemical formula 1-3.

6. In paragraph 2, The heterocyclic compound represented by the above chemical formula 1-4 is a heterocyclic compound represented by any one of the following chemical formulas 1-4a to 1-4d: [Chemical Formula 1-4a] [Chemical Formula 1-4b] [Chemical Formula 1-4c] [Chemical formula 1-4d] In the above chemical formulas 1-4a to 1-4d, The above X1, X2, R3, R5 and b are the same as the definitions in the above chemical formula 1, The above L1 to L3, c to e, Ar1 and Ar2 are the same as the definitions in the above chemical formula 2, The above L4, f and Ar3 are the same as the definitions of the above chemical formula 3, The above R12 and h are the same as defined in the above chemical formula 1-4.

7. 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.

8. 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: .

9. 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 8.

10. In paragraph 9, The above organic layer includes a hole transport layer, An organic light-emitting device, wherein the hole transport layer comprises the heterocyclic compound.

11. In paragraph 9, The above organic layer includes an electron blocking layer, An organic light-emitting device, wherein the electron-blocking layer comprises the heterocyclic compound.

12. In paragraph 9, The above organic layer includes a light-emitting layer, An organic light-emitting device, wherein the light-emitting layer comprises the heterocyclic compound.

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

14. In paragraph 9, 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 light-emitting auxiliary 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.

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