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

Abstract

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

Description

Heterocyclic compounds, organic light-emitting devices containing the same, and compositions for organic layers

[0001] The present application claims the benefit of priority based on Korean Patent Application No. 10-2024-0125699 filed September 13, 2024 and Korean Patent Application No. 10-2025-0087622 filed July 1, 2025, and includes all contents disclosed in the documents of said Korean patent applications as part of this specification.

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

[0003]

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

[0005] An organic light-emitting diode has a structure in which an organic thin film is placed between two electrodes. When voltage is applied to an organic light-emitting diode with such a structure, electrons and holes injected from the two electrodes combine in the organic thin film to form pairs and then annihilate, emitting light. The organic thin film can be composed of a single layer or multiple layers as needed.

[0006] The materials of organic thin films may possess luminescence capabilities as needed. For example, compounds capable of independently constituting an emissive layer may be used as organic thin film materials, or compounds capable of acting as a host or dopant in a host-dopant emissive layer may be used. Furthermore, compounds capable of performing functions such as hole injection, hole transport, electron blocking, electron transport, and electron injection may also be used as organic thin film materials.

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

[0008]

[0009] [Prior Literature]

[0010] [Patent Literature]

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

[0012]

[0013] The present invention aims to provide a heterocyclic compound, an organic light-emitting device containing the same, and a composition for an organic layer.

[0014]

[0015] In order to achieve the above objective,

[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 Y is O; or S, and

[0021] The above R1 to R5 are the same or different from each other and each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C2 to C60 alkenyl group; substituted or unsubstituted C2 to C60 alkynyl group; substituted or unsubstituted C1 to C60 alkoxy group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or unsubstituted C2 to C60 heterocycloalkyl group; substituted or unsubstituted C6 to C60 aryl group; substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R101R102; -SiR101R102R103; and -NR101R102, or a C6 to C60 aromatic hydrocarbon ring substituted or unsubstituted by two or more adjacent groups bonded to each other; or forming a substituted or unsubstituted C2 to C60 heterocyclic group, wherein R101, R102, and R103 are the same or different from each other, and each is 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, and

[0022] The above a1 is an integer from 0 to 4, and if a1 is 2 or greater, R1 are the same or different from each other, and

[0023] The above a2 is an integer from 0 to 4, and if a2 is 2 or greater, R2 are the same or different from each other, and

[0024] The above a3 is an integer from 0 to 4, and if a3 is 2 or greater, R3 are the same or different from each other, and

[0025] The above a4 is an integer from 0 to 3, and if a4 is 2 or greater, R4 are the same or different from each other, and

[0026] The above a5 is an integer from 0 to 4, and if a5 is 2 or greater, R5 are the same or different from each other, and

[0027] The above L1 and L2 are the same or different from each other and are each independently directly bonded; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, and

[0028] The above b1 is an integer from 0 to 5, and if b1 is 2 or greater, L1 are the same or different from each other, and

[0029] The above b2 is an integer from 0 to 5, and if b2 is 2 or greater, L2 are the same or different from each other, and

[0030] The above Ar1 and Ar2 are the same or different from each other and are each independently substituted or unsubstituted C6 to C60 aryl groups; or substituted or unsubstituted C2 to C60 heteroaryl groups.

[0031]

[0032] In addition, the present invention

[0033] First electrode;

[0034] A second electrode provided opposite to the first electrode; and

[0035] An organic light-emitting device comprising one or more organic layers provided between the first electrode and the second electrode,

[0036] An organic light-emitting device is provided in which at least one of the above organic layers comprises a heterocyclic compound represented by Chemical Formula 1 of the present invention.

[0037]

[0038] In addition, the present invention provides an organic light-emitting device in which the organic layer further comprises a heterocyclic compound represented by the following chemical formula 2 or chemical formula 3.

[0039] [Chemical Formula 2]

[0040]

[0041] [Chemical Formula 3]

[0042]

[0043] In the above chemical formulas 2 and 3,

[0044] The above R11, R12, R21, and R22 are the same or different from each other and each independently hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C2 to C60 alkenyl group; substituted or unsubstituted C2 to C60 alkynyl group; substituted or unsubstituted C1 to C60 alkoxy group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or unsubstituted C2 to C60 heterocycloalkyl group; substituted or unsubstituted C6 to C60 aryl group; substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R201R202; -SiR201R202R203; Selected from the group consisting of -NR201R202, or a C6 to C60 aromatic hydrocarbon ring that is substituted or unsubstituted by combining two or more adjacent groups; or a C2 to C60 heterocyclic ring that is substituted or unsubstituted, wherein R201, R202, and R203 are the same or different from each other and each independently comprises a C1 to C60 alkyl group that is substituted or unsubstituted; a C6 to C60 aryl group that is substituted or unsubstituted; or a C2 to C60 heteroaryl group that is substituted or unsubstituted, and

[0045] The above c1 is an integer from 0 to 7, and if c1 is 2 or greater, R11 are the same or different from each other, and

[0046] The above c2 is an integer from 0 to 7, and if c2 is 2 or greater, R12 are the same or different from each other, and

[0047] The above e1 is an integer from 0 to 6, and if e1 is 2 or greater, R21 are the same or different from each other, and

[0048] The above e2 is an integer from 0 to 4, and if e2 is 2 or greater, R22 are the same or different from each other, and

[0049] The above Ar11, Ar12, Ar21, and Ar22 are the same or different from each other and are each independently substituted or unsubstituted C6 to C60 aryl groups; or substituted or unsubstituted C2 to C60 heteroaryl groups, and

[0050] The above L11, L12, L21, and L22 are the same or different from each other and are each independently directly bonded; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, and

[0051] The above d1 is an integer from 0 to 5, and if d1 is 2 or greater, L11 are the same or different from each other, and

[0052] The above d2 is an integer from 0 to 5, and if d2 is 2 or greater, L12 are the same or different from each other, and

[0053] The above f1 is an integer from 0 to 5, and if f1 is 2 or greater, L21 are the same or different from each other, and

[0054] The above f2 is an integer from 0 to 5, and if f2 is 2 or more, L22 are the same or different.

[0055]

[0056] In addition, the present invention provides a composition for an organic layer comprising a heterocyclic compound represented by Formula 1 and a heterocyclic compound represented by Formula 2 or Formula 3.

[0057]

[0058] The compounds described in this specification can be used as organic layer materials for organic light-emitting devices. The compounds can serve as hole injection layer materials, hole transport layer materials, light-emitting layer materials, electron transport layer materials, electron injection layer materials, etc., in organic light-emitting devices. In particular, the compounds can be used as light-emitting layer materials for organic light-emitting devices, and the compounds can be used as light-emitting materials alone, or as host materials or dopant materials for the light-emitting layer.

[0059] Specifically, the above compound may be used alone as a light-emitting material, or as a host material or dopant material of a light-emitting layer. When the heterocyclic compound represented by Chemical Formula 1 is used in the organic layer, the driving voltage of the organic light-emitting device can be lowered, the light-emitting efficiency can be improved, and the lifespan characteristics can be improved.

[0060]

[0061] FIGS. 1 to 3 are schematic diagrams illustrating the stacked structure of an organic light-emitting device according to one embodiment of the present invention.

[0062]

[0063] The present invention will be described in more detail below.

[0064]

[0065] 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 substitution location is not limited to the location where the hydrogen atom is substituted, that is, any location where a substituent can be substituted, and in the case of two or more substitutions, the two or more substituents may be the same or different from each other.

[0066] In this specification, "substituted or unsubstituted" means deuterium; halogen; cyano group; a straight-chain or branched-chain alkyl group of C1 to C60; a straight-chain or branched-chain alkenyl group of C2 to C60; a straight-chain or branched-chain alkynyl group of C2 to C60; a straight-chain, branched, or cyclic alkoxy group of C1 to C60; a monocyclic or polycyclic cycloalkyl group of C3 to C60; a monocyclic or polycyclic heterocycloalkyl group of C2 to C60; a monocyclic or polycyclic aryl group of C6 to C60; a monocyclic or polycyclic heteroaryl group of C2 to C60; -SiRR'R"; -P(=O)RR'; means being substituted or unsubstituted with one or more substituents selected from the group consisting of C1 to C20 alkylamine groups; C6 to C60 monocyclic or polycyclic arylamine groups; and C2 to C60 monocyclic or polycyclic heteroarylamine groups, or being substituted or unsubstituted with two or more substituents selected from the exemplified substituents connected to a substituent, wherein R, R' and R" are the same or different from each other and are each independently substituted or unsubstituted C1 to C60 alkyl groups; substituted or unsubstituted C6 to C60 aryl groups; or substituted or unsubstituted C2 to C60 heteroaryl groups.

[0067] In this specification, the halogen may be fluorine; chlorine; bromine; or iodine.

[0068] In this specification, the alkyl group comprises a straight or branched chain having 1 to 60 carbon atoms and may be further substituted by other substituents. The number of carbon atoms of the alkyl group may be 1 to 60, specifically 1 to 40, and more specifically 1 to 20. 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; an 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.

[0069] In this specification, the alkenyl group comprises a straight or branched chain having 2 to 60 carbon atoms and may be further substituted by other substituents. The number of carbon atoms of the alkenyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20. Specific examples include a vinyl group; 1-propenyl group; isopropenyl group; 1-butenyl group; 2-butenyl group; 3-butenyl group; 1-pentenyl group; 2-pentenyl group; 3-pentenyl group; 3-methyl-1-butenyl group; 1,3-butadienyl group; allyl group; 1-phenylvinyl-1-yl group; 2-phenylvinyl-1-yl group; 2,2-diphenylvinyl-1-yl group; 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., are included but are not limited thereto.

[0070] In the present specification, the alkynyl group comprises a straight or branched chain having 2 to 60 carbon atoms and may be further substituted by other substituents. The number of carbon atoms of the alkynyl group may be 2 to 60, specifically 2 to 40, more specifically 2 to 20.

[0071] In the present specification, the alkoxy group may be a straight chain, a branched chain, or a cyclic chain. The number of carbon atoms in the alkoxy group is not particularly limited, but it is preferred to have 1 to 20 carbon atoms. Specifically, methoxy group; ethoxy group; n-propoxy group; isopropoxy group; n-butoxy group; isobutoxy group; tert-butoxy group; sec-butoxy group; n-pentyloxy group; neopentyloxy group; isopentyloxy group; n-hexyloxy group; 3,3-dimethylbutyloxy group; 2-ethylbutyloxy group; n-octyloxy group; n-nonyloxy group; n-decyloxy group; benzyloxy group; p-methylbenzyloxy group, etc., are included but are not limited thereto.

[0072] In this specification, the cycloalkyl group comprises a monocyclic or polycyclic group having 3 to 60 carbon atoms and may be further substituted by other substituents. Here, polycyclic means a group in which the 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 a different type of ring group; for example, a heterocycloalkyl group; an aryl group; a heteroaryl group, etc. The number of carbon atoms of the cycloalkyl group may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20. Specifically, cyclopropyl group; cyclobutyl group; cyclopentyl group; 3-methylcyclopentyl group; 2,3-dimethylcyclopentyl group; cyclohexyl group; 3-methylcyclohexyl group; 4-methylcyclohexyl group; 2,3-dimethylcyclohexyl group; 3,4,5-trimethylcyclohexyl group; 4-tert-butylcyclohexyl group; Cycloheptyl groups; cyclooctyl groups, etc., are included, but are not limited thereto.

[0073] In this specification, the heterocycloalkyl group comprises O; S; Se; N; or Si as a heteroatom, comprises a monocyclic or polycyclic group having 2 to 60 carbon atoms, and may be further substituted by other substituents. Here, polycyclic means a group in which the 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 a different type of ring group; for example, a cycloalkyl group; an aryl group; a heteroaryl group, etc. The number of carbon atoms of the heterocycloalkyl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 20.

[0074] In this specification, the aryl group comprises a monocyclic or polycyclic group having 6 to 60 carbon atoms and may be further substituted by other substituents. Here, polycyclic means a group in which the 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 a different type of ring group; for example, a cycloalkyl group; a heterocycloalkyl group; a heteroaryl group, etc. The aryl group may include a spiro group. The number of carbon atoms of the aryl group may be 6 to 60, specifically 6 to 40, and more specifically 6 to 20. 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; and an indenyl group. Acenaphthylenyl group; benzofluorenyl group; spirobifluorenyl group; 2,3-dihydro-1H-denyl group; condensed rings thereof, etc., but are not limited thereto.

[0075] In this specification, the phosphine oxide group is represented as -P(=O)R101R102, where R101 and R102 are identical or different from each other and may each be a substituent consisting of at least one of hydrogen; deuterium; halogen group; alkyl group; alkenyl group; alkoxy group; cycloalkyl group; aryl group; and heterocyclic group. Specifically, it may be substituted with an aryl group, and the examples described above may apply to the aryl group. For example, the phosphine oxide group may include a diphenylphosphine oxide group; a dinaphthylphosphine oxide group, etc., but is not limited thereto.

[0076] In the present specification, the silyl group is a substituent comprising Si, wherein the Si atom is directly connected as a radical and is represented as -SiR101R102R103, and R101 to R103 are identical or different from each other and may each be a substituent consisting of at least one of hydrogen; deuterium; halogen group; alkyl group; alkenyl group; alkoxy group; cycloalkyl group; aryl group; and heterocyclic group. Specific examples of the silyl group include, but are not limited to, trimethylsilyl group; triethylsilyl group; t-butyldimethylsilyl group; vinyldimethylsilyl group; propyldimethylsilyl group; triphenylsilyl group; diphenylsilyl group; phenylsilyl group.

[0077] In the present specification, the fluorenyl group may be substituted, and adjacent substituents may combine with each other to form a ring.

[0078] When the above fluorenyl group is substituted, It may include, but is not limited to, etc.

[0079] In the present specification, the spiro group is a group comprising a spiro structure and may have 15 to 60 carbon atoms. For example, the spiro group may comprise a structure in which a 2,3-dihydro-1H-indene group or a cyclohexane group is spiro-bonded to a fluorenyl group. Specifically, the spiro group may comprise any one of the groups of the following structural formulas.

[0080]

[0081] In this specification, the heteroaryl group comprises S; O; Se; N; or Si as a heteroatom, and comprises a monocyclic or polycyclic group having 2 to 60 carbon atoms, and may be further substituted by other substituents. Here, the polycyclic group means a group in which the 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 a different type of ring group, such as a cycloalkyl group; a heterocycloalkyl group; an aryl group, etc. The number of carbon atoms of the heteroaryl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 25.Specific examples of the above heteroaryl group include pyridyl group; pyrrolyl group; pyrimidyl group; pyridazolyl group; furanyl group; thiophenyl group; imidazolyl group; pyrazolyl group; oxazolyl group; isoxazolyl group; thiazolyl group; isothiazolyl group; triazolyl group; furazanyl group; oxadiazolyl group; thiadiazolyl group; dithiazolyl group; tetrazolyl group; pyranyl group; thiopyranyl group; diazinyl group; oxazolyl group; thiazolyl group; deoxynyl group; triazinyl group; tetrazolyl group; quinolyl group; isoquinolyl group; quinazolinyl group; isoquinazolinyl group; quinozolinyl group; naphthalidyl group; acrridinyl group; phenantridinyl group; imidazopyridinyl group; diazanaphthalenyl group; Triazydenyl group; 2-Indolyl group; Indolizinyl group; Benzothiazolyl group; Benzooxazolyl group; Benzimidazolyl group; Benzothiophenyl group; Benzofuranyl group; Dibenzothiophenyl group; Dibenzofuranyl group; Carbazolyl group; Benzocarbazolyl group; Dibenzocarbazolyl group; Phenazinyl group; Dibenzosilol group; Spirobi(Dibenzosilol) group; Dihydrophenazinyl group; Phenoxazinyl group; Phenantridyl group; Thienyl group; Indolo[2,3-a]carbazolyl group; Indolo[2,3-b]carbazolyl group; Indolinyl group; 10,11-Dihydro-Dibenzo[b,f]azefinyl group; 9,10-Dihydroacridinyl group; Phenanthrazinyl group; Phenothiazinyl group; Examples include phthalazinyl group; naphthylidinyl group; phenanthrolinyl group; benzo[c][1,2,5]thiadiazolyl group; 5,10-dihydrodibenzo[b,e][1,4]azacillinyl group; pyrazolo[1,5-c]quinazolinyl group; pyrido[1,2-b]indazolyl group; pyrido[1,2-a]imidazo[1,2-e]indolinyl group; 5,11-dihydroindeno[1,2-b]carbazolyl group, but are not limited thereto.

[0082] In this specification, the amine group may be selected from the group consisting of monoalkylamine group; monoarylamine group; monoheteroarylamine group; -NH2; dialkylamine group; diarylamine group; diheteroarylamine group; alkylarylamine group; alkylheteroarylamine group; and 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 methylamine group; dimethylamine group; ethylamine group; diethylamine group; phenylamine group; naphthylamine group; biphenylamine group; dibiphenylamine group; anthracenylamine group; 9-methyl-anthracenylamine group; diphenylamine group; phenylnaphthylamine group; ditolylamine group; phenyltolylamine group; triphenylamine group; biphenylnaphthylamine group; phenylbiphenylamine group; biphenylfluorenylamine group; phenyltriphenylenylamine group; There are, but are not limited to, biphenyltriphenyllenylamine groups.

[0083] In this specification, an arylene group refers to a group having two binding sites to an aryl group, i.e., a divalent group. Except for the fact that each of these is a divalent group, the description of the arylene group described above may apply. Additionally, a heteroarylene group refers to a group having two binding sites to a heteroaryl group, i.e., a divalent group. Except for the fact that each of these is a divalent group, the description of the heteroaryl group described above may apply.

[0084] In this specification, "adjacent" groups may mean a substituent substituted on an atom directly connected to the atom on which the substituent is substituted; a substituent located closest to the substituent in stereostructure; or another substituent substituted on the atom on which the substituent is substituted. 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" groups to each other.

[0085] In the present invention, "where 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 can be deuterium.

[0086] In one embodiment of the present invention, "when no substituents are indicated in the chemical formula or compound structure" may mean that all positions where substituents may be present are hydrogen or deuterium. That is, in the case of deuterium, it is an isotope of hydrogen, and some hydrogen atoms may be deuterium isotopes, and in this case, the content of deuterium may be 0% to 100%.

[0087] In one embodiment of the present invention, in the case where "substituents are not indicated in the chemical formula or compound structure," if deuterium is not explicitly excluded, such as "deuterium content is 0%," "hydrogen content is 100%," or "substituents are all hydrogen," hydrogen and deuterium may be used in a mixture in the compound.

[0088] In one embodiment of the present invention, deuterium is one of the isotopes of hydrogen and is an element having a deuteron, composed of one proton and one neutron, as its nucleus, wherein hydrogen -2 It can be expressed as, and the element symbol is D or 2 It can also be written as H.

[0089] In one embodiment of the present invention, an isotope, which refers to atoms having the same atomic number (Z) but different mass numbers (A), can also be interpreted as an element having the same number of protons but different numbers of neutrons.

[0090] In one embodiment of the present invention, the meaning of the content T% of a specific substituent can be defined as T2 / T1X100 = T% when the total number of substituents that a basic compound may have is defined as T1 and the number of specific substituents among them is defined as T2.

[0091] That is, in one example, A deuterium content of 20% in a phenyl group represented by 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, a deuterium content of 20% in a phenyl group can be represented by the following structural formula.

[0092]

[0093] In addition, in one embodiment of the present invention, "phenyl group having 0% deuterium content" may mean a phenyl group that does not contain deuterium atoms, i.e., has five hydrogen atoms.

[0094] In the present invention, the C6 to C60 aromatic hydrocarbon ring refers to a compound comprising an aromatic ring composed of C6 to C60 carbons and hydrogens, and examples include, but are not limited to, phenyl group; biphenyl group; terphenyl group; triphenylenyl group; naphthyl group; anthracenyl group; phenalenyl group; phenanthrenyl group; fluorenyl group; pyrenyl group; chrysenyl group; perylenyl group; azulenyl group, etc., and include all aromatic hydrocarbon ring compounds known in the art that satisfy the above number of carbons.

[0095]

[0096] The present invention provides a heterocyclic compound represented by the following chemical formula 1.

[0097] [Chemical Formula 1]

[0098]

[0099] In the above chemical formula 1,

[0100] The above Y is O; or S, and

[0101] The above R1 to R5 are the same or different from each other and each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C2 to C60 alkenyl group; substituted or unsubstituted C2 to C60 alkynyl group; substituted or unsubstituted C1 to C60 alkoxy group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or unsubstituted C2 to C60 heterocycloalkyl group; substituted or unsubstituted C6 to C60 aryl group; substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R101R102; -SiR101R102R103; and -NR101R102, or a C6 to C60 aromatic hydrocarbon ring substituted or unsubstituted by two or more adjacent groups bonded to each other; or forming a substituted or unsubstituted C2 to C60 heterocyclic group, wherein R101, R102, and R103 are the same or different from each other, and each is 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, and

[0102] The above a1 is an integer from 0 to 4, and if a1 is 2 or greater, R1 are the same or different from each other, and

[0103] The above a2 is an integer from 0 to 4, and if a2 is 2 or greater, R2 are the same or different from each other, and

[0104] The above a3 is an integer from 0 to 4, and if a3 is 2 or greater, R3 are the same or different from each other, and

[0105] The above a4 is an integer from 0 to 3, and if a4 is 2 or greater, R4 are the same or different from each other, and

[0106] The above a5 is an integer from 0 to 4, and if a5 is 2 or greater, R5 are the same or different from each other, and

[0107] The above L1 and L2 are the same or different from each other and are each independently directly bonded; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, and

[0108] The above b1 is an integer from 0 to 5, and if b1 is 2 or greater, L1 are the same or different from each other, and

[0109] The above b2 is an integer from 0 to 5, and if b2 is 2 or greater, L2 are the same or different from each other, and

[0110] The above Ar1 and Ar2 are the same or different from each other and are each independently substituted or unsubstituted C6 to C60 aryl groups; or substituted or unsubstituted C2 to C60 heteroaryl groups.

[0111]

[0112] In one embodiment of the present invention, Y may be O.

[0113] In another embodiment of the present invention, Y may be S.

[0114]

[0115] In one embodiment of the present invention, R1 to R5 are the same or different from one another and each independently hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to C30 alkyl group; substituted or unsubstituted C2 to C30 alkenyl group; substituted or unsubstituted C2 to C30 alkynyl group; substituted or unsubstituted C1 to C30 alkoxy group; substituted or unsubstituted C3 to C30 cycloalkyl group; substituted or unsubstituted C2 to C30 heterocycloalkyl group; substituted or unsubstituted C6 to C30 aryl group; substituted or unsubstituted C2 to C30 heteroaryl group; -P(=O)R101R102; -SiR101R102R103; Or -NR101R102, or two or more adjacent groups may be bonded to each other to form a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C30 hetero ring, wherein R101, R102, and R103 are the same or different from each other and each may independently 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.

[0116] In another embodiment of the present invention, R1 to R5 are the same or different from one another and each independently hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to C20 alkyl group; substituted or unsubstituted C2 to C20 alkenyl group; substituted or unsubstituted C2 to C20 alkynyl group; substituted or unsubstituted C1 to C20 alkoxy group; substituted or unsubstituted C3 to C20 cycloalkyl group; substituted or unsubstituted C2 to C20 heterocycloalkyl group; substituted or unsubstituted C6 to C20 aryl group; substituted or unsubstituted C2 to C20 heteroaryl group; -P(=O)R101R102; -SiR101R102R103; Or -NR101R102, or two or more adjacent groups may be bonded to each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C20 hetero ring, wherein R101, R102, and R103 are the same or different from each other and each may independently 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.

[0117] In another embodiment of the present invention, R1 to R5 may be the same or different from one another and may each independently be hydrogen; deuterium; halogen; cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0118] In another embodiment of the present invention, R1 to R5 may be the same or different from one another and may each independently be hydrogen; deuterium; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0119] In another embodiment of the present invention, R1 may be hydrogen; deuterium; or a substituted or unsubstituted C6 to C60 aryl group.

[0120] In another embodiment of the present invention, R1 may be hydrogen; deuterium; or a substituted or unsubstituted C6 to C30 aryl group.

[0121] In another embodiment of the present invention, R1 may be hydrogen; deuterium; or a substituted or unsubstituted C6 to C20 aryl group.

[0122] In another embodiment of the present invention, R1 may be hydrogen; deuterium; or a substituted or unsubstituted phenyl group.

[0123] In another embodiment of the present invention, R4 and R5 may be the same or different from each other and may each independently be hydrogen; or deuterium.

[0124] In another embodiment of the present invention, R2 and R3 may be the same or different from each other and may each independently be hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0125] In another embodiment of the present invention, R2 and R3 may be the same or different from each other and may each independently be hydrogen; deuterium; a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0126] In another embodiment of the present invention, R2 and R3 may be the same or different from each other and may each independently be hydrogen; deuterium; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0127] In another embodiment of the present invention, R2 and R3 may be the same or different from each other and may each independently be hydrogen; deuterium; a substituted or unsubstituted methyl group; a substituted or unsubstituted isobutyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted dibenzothiophenyl group; or a substituted or unsubstituted carbazolyl group.

[0128]

[0129] In one embodiment of the present invention, Ar1 and Ar2 may be the same or different from each other and may each be an independently substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0130] In another embodiment of the present invention, Ar1 and Ar2 may be the same or different from each other and may each be an independently substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0131] In another embodiment of the present invention, Ar1 and Ar2 are the same or different from each other and may each independently be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted triphenylenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted spirobifluorenyl group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted dibenzothiophenyl group; or a substituted or unsubstituted carbazolyl group.

[0132] In another embodiment of the present invention, the Ar1 may be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted triphenylenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted spirobifluorenyl group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted dibenzothiophenyl group; or a substituted or unsubstituted carbazolyl group.

[0133] In another embodiment of the present invention, the Ar2 may be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted triphenylenyl group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted dibenzothiophenyl group; or a substituted or unsubstituted carbazolyl group.

[0134]

[0135] In one embodiment of the present invention, L1 and L2 may be the same or different from each other and may each be independently directly bonded; a substituted or unsubstituted C6 to C30 arylene group; or a substituted or unsubstituted C2 to C30 heteroarylene group.

[0136] In another embodiment of the present invention, L1 and L2 may be the same or different from each other and may each be independently directly bonded; a substituted or unsubstituted C6 to C20 arylene group; or a substituted or unsubstituted C2 to C20 heteroarylene group.

[0137] In another embodiment of the present invention, L1 and L2 may be the same or different from each other and each may be independently directly bonded; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted dibenzofuranylene group; a substituted or unsubstituted dibenzothiophenylene group; or a substituted or unsubstituted carbazolilene group.

[0138] In another embodiment of the present invention, L1 may be a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted dibenzofuranylene group; a substituted or unsubstituted dibenzothiophenylene group; or a substituted or unsubstituted carbazolilene group.

[0139] In another embodiment of the present invention, the L2 may be a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted carbazolilene group.

[0140]

[0141] In one embodiment of the present invention, the heterocyclic compound represented by the chemical formula 1 may be represented by either the following chemical formula 1-1 or 1-2.

[0142] [Chemical Formula 1-1]

[0143]

[0144] [Chemical Formula 1-2]

[0145]

[0146] In the above chemical formulas 1-1 and 1-2,

[0147] The above a6 is an integer from 0 to 2, and if a6 is 2 or greater, R4 are the same or different from each other, and

[0148] The above a7 is an integer from 0 to 3, and if a7 is 2 or greater, R5 are the same or different from each other, and

[0149] The above Y, R1 to R5, L1, L2, Ar1, Ar2, a1 to a5, b1 and b2 are identical to the definitions of Chemical Formula 1.

[0150]

[0151] In one embodiment of the present invention, the heterocyclic compound represented by the formula 1-1 may be represented by any one of the following formulas 1-1-1 to 1-1-4.

[0152] [Chemical Formula 1-1-1]

[0153]

[0154] [Chemical Formula 1-1-2]

[0155]

[0156] [Chemical Formula 1-1-3]

[0157]

[0158] [Chemical Formula 1-1-4]

[0159]

[0160] In the above chemical formulas 1-1-1 to 1-1-4,

[0161] The above Y, R1 to R5, L1, L2, Ar1, Ar2, a1 to a3, a5, b1 and b2 are identical to the definitions of Chemical Formula 1, and

[0162] The above a6 is identical to the definition of chemical formula 1-1.

[0163]

[0164] In one embodiment of the present invention, the heterocyclic compound represented by the chemical formula 1-2 may be represented by any one of the following chemical formulas 1-2-1 to 1-2-4.

[0165] [Chemical Formula 1-2-1]

[0166]

[0167] [Chemical Formula 1-2-2]

[0168]

[0169] [Chemical Formula 1-2-3]

[0170]

[0171] [Chemical Formula 1-2-4]

[0172]

[0173] In the above chemical formulas 1-2-1 to 1-2-4,

[0174] The above Y, R1 to R5, L1, L2, Ar1, Ar2, a1 to a4, b1 and b2 are identical to the definitions of Chemical Formula 1, and

[0175] The above a7 is identical to the definition of chemical formula 1-2.

[0176]

[0177] In one embodiment of the present invention, R1 to R5, L1, L2, Ar1 and Ar2 may all include undeuterated hydrogen (H).

[0178] In another embodiment of the present invention, at least one of R1 to R5, L1, L2, Ar1 and Ar2 comprises deuterium (D), and at least one of R1 to R5, L1, L2, Ar1 and Ar2 may comprise undeuterinized hydrogen.

[0179] In another embodiment of the present invention, R1 to R5, L1, L2, Ar1 and Ar2 may all include deuterium.

[0180]

[0181] In one embodiment of the present invention, the heterocyclic compound represented by Formula 1 may not include deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be, for example, greater than 0%, greater than 1%, greater than 10%, greater than 20%, greater than 30%, greater than 40%, or greater than 50%, and less than 100%, less than 90%, less than 80%, less than 70%, or less than 60%.

[0182] In another embodiment of the present invention, the heterocyclic compound represented by Formula 1 may not include deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be 1% to 100%.

[0183] In another embodiment of the present invention, the heterocyclic compound represented by Formula 1 may not include deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be 20% to 90%.

[0184] In another embodiment of the present invention, the heterocyclic compound represented by Formula 1 may not include deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be 30% to 80%.

[0185] In another embodiment of the present invention, the heterocyclic compound represented by Formula 1 may not include deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be 50% to 70%.

[0186]

[0187] 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.

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222] In addition, by introducing various substituents into the structure of Chemical Formula 1, compounds having the 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, materials that satisfy the conditions required for each organic layer can be synthesized.

[0223] In addition, by introducing various substituents into the structure of Chemical Formula 1 above, the energy band gap can be finely controlled, while at the same time, the properties at the interface between organic materials can be improved and the applications of the material can be diversified.

[0224] Meanwhile, the above-mentioned heterocyclic compound exhibits excellent thermal stability due to its high glass transition temperature (Tg). This increase in thermal stability is an important factor in providing operational stability to the device.

[0225] A heterocyclic compound according to one embodiment of the present invention can be prepared by a multi-step chemical reaction. Some intermediate compounds may be prepared first, and the compound of Formula 1 may be prepared from the intermediate compounds. More specifically, a heterocyclic compound according to one embodiment of the present invention may be prepared based on the preparation example described below.

[0226]

[0227] Another embodiment of the present invention provides an organic light-emitting device comprising a heterocyclic compound represented by the chemical formula 1. The "organic light-emitting device" may be expressed using terms such as "organic light-emitting diode," "OLED (Organic Light Emitting Diodes)," "OLED device," or "organic electroluminescent device."

[0228]

[0229] In addition, the present invention

[0230] First electrode;

[0231] A second electrode provided opposite to the first electrode; and

[0232] An organic light-emitting device comprising one or more organic layers provided between the first electrode and the second electrode,

[0233] The present invention relates to an organic light-emitting device in which one or more of the above organic layers comprise a heterocyclic compound represented by the above chemical formula 1.

[0234]

[0235] In one embodiment of the present invention, the first electrode may be an anode, and the second electrode may be a cathode.

[0236] In another embodiment, the first electrode may be a negative electrode and the second electrode may be a positive electrode.

[0237]

[0238] In one embodiment of the present invention, the organic light-emitting element may be a red organic light-emitting element, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material for a red organic light-emitting material.

[0239] In another embodiment of the present invention, the organic light-emitting element may be a blue organic light-emitting element, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material for a blue organic light-emitting material.

[0240] In another embodiment of the present invention, the organic light-emitting element may be a green organic light-emitting element, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material for a green organic light-emitting material.

[0241]

[0242] In one embodiment of the present invention, the organic light-emitting element may be a red organic light-emitting element, and the heterocyclic compound represented by Chemical Formula 1 may be used as a light-emitting layer material of the red organic light-emitting element.

[0243] 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 Chemical Formula 1 may be used as a light-emitting layer material of the blue organic light-emitting device.

[0244] 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 Chemical Formula 1 may be used as a light-emitting layer material of the green organic light-emitting device.

[0245]

[0246] The specific details regarding the heterocyclic compound represented by the above chemical formula 1 are the same as those previously described.

[0247]

[0248] The organic light-emitting device of the present invention can be manufactured by conventional methods and materials for manufacturing organic light-emitting devices, except that one or more organic layers are formed using the aforementioned heterocyclic compound.

[0249] The above heterocyclic compound can be formed as an organic layer by vacuum deposition as well as by solution coating when manufacturing an organic light-emitting device. Here, solution coating refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.

[0250] 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 stacked. For example, the organic light-emitting device of the present invention may have a structure comprising a hole injection layer, an electron blocking layer, a hole transport layer, a light-emitting layer, an electron transport layer, a hole blocking layer, an electron injection layer, etc. as organic layers. However, the structure of the organic light-emitting device is not limited thereto and may include a smaller number of organic layers.

[0251]

[0252] In the organic light-emitting device of the present invention, the organic layer comprises a light-emitting layer, and the light-emitting layer may comprise a heterocyclic compound represented by Chemical Formula 1. When the heterocyclic compound is used in the light-emitting layer, the driving efficiency and lifespan of the organic light-emitting device can be improved because strong charge transfer is possible by spatially separating the HOMO (Highest Occupied Molecular Orbital) and LUMO (Lowest Unoccupied Molecular Orbital).

[0253]

[0254] In an organic light-emitting device according to one embodiment of the present invention, the organic layer comprising the heterocyclic compound represented by Formula 1 further comprises a heterocyclic compound represented by Formula 2 or Formula 3, thereby providing an organic light-emitting device.

[0255] [Chemical Formula 2]

[0256]

[0257] [Chemical Formula 3]

[0258]

[0259] In the above chemical formulas 2 and 3,

[0260] The above R11, R12, R21, and R22 are the same or different from each other and each independently hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C2 to C60 alkenyl group; substituted or unsubstituted C2 to C60 alkynyl group; substituted or unsubstituted C1 to C60 alkoxy group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or unsubstituted C2 to C60 heterocycloalkyl group; substituted or unsubstituted C6 to C60 aryl group; substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R201R202; -SiR201R202R203; Selected from the group consisting of -NR201R202, or a C6 to C60 aromatic hydrocarbon ring that is substituted or unsubstituted by combining two or more adjacent groups; or a C2 to C60 heterocyclic ring that is substituted or unsubstituted, wherein R201, R202, and R203 are the same or different from each other and each independently comprises a C1 to C60 alkyl group that is substituted or unsubstituted; a C6 to C60 aryl group that is substituted or unsubstituted; or a C2 to C60 heteroaryl group that is substituted or unsubstituted, and

[0261] The above c1 is an integer from 0 to 7, and if c1 is 2 or greater, R11 are the same or different from each other, and

[0262] The above c2 is an integer from 0 to 7, and if c2 is 2 or greater, R12 are the same or different from each other, and

[0263] The above e1 is an integer from 0 to 6, and if e1 is 2 or greater, R21 are the same or different from each other, and

[0264] The above e2 is an integer from 0 to 4, and if e2 is 2 or greater, R22 are the same or different from each other, and

[0265] The above Ar11, Ar12, Ar21, and Ar22 are the same or different from each other and are each independently substituted or unsubstituted C6 to C60 aryl groups; or substituted or unsubstituted C2 to C60 heteroaryl groups, and

[0266] The above L11, L12, L21, and L22 are the same or different from each other and are each independently directly bonded; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, and

[0267] The above d1 is an integer from 0 to 5, and if d1 is 2 or greater, L11 are the same or different from each other, and

[0268] The above d2 is an integer from 0 to 5, and if d2 is 2 or greater, L12 are the same or different from each other, and

[0269] The above f1 is an integer from 0 to 5, and if f1 is 2 or greater, L21 are the same or different from each other, and

[0270] The above f2 is an integer from 0 to 5, and if f2 is 2 or more, L22 are the same or different.

[0271]

[0272] In one embodiment of the present invention, R11, R12, R21, and R22 are the same or different from each other and each independently hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to C30 alkyl group; substituted or unsubstituted C2 to C30 alkenyl group; substituted or unsubstituted C2 to C30 alkynyl group; substituted or unsubstituted C1 to C30 alkoxy group; substituted or unsubstituted C3 to C30 cycloalkyl group; substituted or unsubstituted C2 to C30 heterocycloalkyl group; substituted or unsubstituted C6 to C30 aryl group; substituted or unsubstituted C2 to C30 heteroaryl group; -P(=O)R201R202; -SiR201R202R203; or -NR201R202, or two or more adjacent groups bonded to each other to form a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C30 hetero ring, wherein R201, R202, and R203 are the same or different from each other and each independently 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.

[0273] In another embodiment of the present invention, R11, R12, R21, and R22 are the same or different from each other and each independently hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to C20 alkyl group; substituted or unsubstituted C2 to C20 alkenyl group; substituted or unsubstituted C2 to C20 alkynyl group; substituted or unsubstituted C1 to C20 alkoxy group; substituted or unsubstituted C3 to C20 cycloalkyl group; substituted or unsubstituted C2 to C20 heterocycloalkyl group; substituted or unsubstituted C6 to C20 aryl group; substituted or unsubstituted C2 to C20 heteroaryl group; -P(=O)R201R202; -SiR201R202R203; or -NR201R202, or two or more adjacent groups bonded to each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C20 hetero ring, wherein R201, R202, and R203 are the same or different from each other and each independently substituted or unsubstituted C1 to C20 alkyl group; substituted or unsubstituted C6 to C20 aryl group; or substituted or unsubstituted C2 to C20 heteroaryl group.

[0274] In another embodiment of the present invention, R11, R12, R21 and R22 may be the same or different from one another and may each independently be hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to C20 alkyl group; substituted or unsubstituted C2 to C20 alkenyl group; substituted or unsubstituted C2 to C20 alkynyl group; substituted or unsubstituted C1 to C20 alkoxy group; substituted or unsubstituted C3 to C20 cycloalkyl group; substituted or unsubstituted C2 to C20 heterocycloalkyl group; substituted or unsubstituted C6 to C20 aryl group; or substituted or unsubstituted C2 to C20 heteroaryl group.

[0275] In another embodiment of the present invention, R11, R12, R21 and R22 may be the same or different from each other and may each independently be hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to C20 alkyl group; substituted or unsubstituted C6 to C20 aryl group; or substituted or unsubstituted C2 to C20 heteroaryl group.

[0276] In another embodiment of the present invention, R11, R12, R21, and R22 may be the same or different from each other and may each independently be hydrogen; or deuterium.

[0277]

[0278] In one embodiment of the present invention, Ar11, Ar12, Ar21, and Ar22 may be the same or different from each other and may each be an independently substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0279] In another embodiment of the present invention, Ar11, Ar12, Ar21, and Ar22 may be the same or different from each other and may each be an independently substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0280] In another embodiment of the present invention, Ar11, Ar12, Ar21 and Ar22 may be the same or different from each other and may each be an independently substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted triphenylenyl group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group.

[0281] In another embodiment of the present invention, the Ar11 may be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted triphenylenyl group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group.

[0282] In another embodiment of the present invention, the Ar12 may be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted terphenyl group.

[0283] In another embodiment of the present invention, the Ar21 may be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted triphenylenyl group; or a substituted or unsubstituted dibenzofuranyl group.

[0284] In another embodiment of the present invention, the Ar22 may be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; or a substituted or unsubstituted dibenzofuranyl group.

[0285]

[0286] In one embodiment of the present invention, L11, L12, L21, and L22 may be the same or different from each other and may each be independently directly bonded; a substituted or unsubstituted C6 to C30 arylene group; or a substituted or unsubstituted C2 to C30 heteroarylene group.

[0287] In another embodiment of the present invention, L11, L12, L21, and L22 may be the same or different from each other and may each be independently directly bonded; a substituted or unsubstituted C6 to C20 arylene group; or a substituted or unsubstituted C2 to C20 heteroarylene group.

[0288] In another embodiment of the present invention, L11, L12, L21 and L22 may be the same or different from each other and may each be independently directly bonded; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; or a substituted or unsubstituted dibenzofuranilene group.

[0289] In another embodiment of the present invention, L11 may be a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; or a substituted or unsubstituted dibenzofuranilene group.

[0290] In another embodiment of the present invention, the L12 may be a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted biphenylene group.

[0291] In another embodiment of the present invention, the L21 may be a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted biphenylene group.

[0292] In another embodiment of the present invention, the L22 may be a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted biphenylene group.

[0293]

[0294] In one embodiment of the present invention, R11, R12, R21, R22, Ar11, Ar12, Ar21, Ar22, L11, L12, L21, and L22 may all include undeuterated hydrogen (H).

[0295] In another embodiment of the present invention, at least one of R11, R12, R21, R22, Ar11, Ar12, Ar21, Ar22, L11, L12, L21, and L22 comprises deuterium (D), and at least one of R11, R12, R21, R22, Ar11, Ar12, Ar21, Ar22, L11, L12, L21, and L22 may comprise undeuterinized hydrogen.

[0296] In another embodiment of the present invention, R11, R12, R21, R22, Ar11, Ar12, Ar21, Ar22, L11, L12, L21, and L22 may all include deuterium.

[0297]

[0298] In one embodiment of the present invention, the heterocyclic compound represented by Formula 2 or the heterocyclic compound represented by Formula 3 may not include deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be, for example, greater than 0%, greater than 1%, greater than 10%, greater than 20%, greater than 30%, greater than 40%, or greater than 50%, and may be less than 100%, less than 90%, less than 80%, less than 70%, or less than 60%.

[0299] In another embodiment of the present invention, the heterocyclic compound represented by Formula 2 or the heterocyclic compound represented by Formula 3 may not include deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be 1% to 100%.

[0300] In another embodiment of the present invention, the heterocyclic compound represented by Formula 2 or the heterocyclic compound represented by Formula 3 may not include deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be 20% to 90%.

[0301] In another embodiment of the present invention, the heterocyclic compound represented by Formula 2 or the heterocyclic compound represented by Formula 3 may not include deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be 30% to 80%.

[0302] In another embodiment of the present invention, the heterocyclic compound represented by Formula 2 or the heterocyclic compound represented by Formula 3 may not include deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be 50% to 70%.

[0303]

[0304] In one embodiment of the present invention, the heterocyclic compound represented by Formula 2 may not include deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be, for example, greater than 0%, greater than 1%, greater than 10%, greater than 20%, greater than 30%, greater than 40%, or greater than 50%, and less than 100%, less than 90%, less than 80%, less than 70%, or less than 60%.

[0305] In another embodiment of the present invention, the heterocyclic compound represented by Formula 2 may not include deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be 1% to 100%.

[0306] In another embodiment of the present invention, the heterocyclic compound represented by Formula 2 may not include deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be 20% to 90%.

[0307] In another embodiment of the present invention, the heterocyclic compound represented by Formula 2 may not include deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be 30% to 80%.

[0308] In another embodiment of the present invention, the heterocyclic compound represented by Formula 2 may not include deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be 50% to 70%.

[0309]

[0310] In one embodiment of the present invention, the heterocyclic compound represented by Formula 3 may not include deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be, for example, greater than 0%, greater than 1%, greater than 10%, greater than 20%, greater than 30%, greater than 40%, or greater than 50%, and less than 100%, less than 90%, less than 80%, less than 70%, or less than 60%.

[0311] In another embodiment of the present invention, the heterocyclic compound represented by Formula 3 may not include deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be 1% to 100%.

[0312] In another embodiment of the present invention, the heterocyclic compound represented by Formula 3 may not include deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be 20% to 90%.

[0313] In another embodiment of the present invention, the heterocyclic compound represented by Formula 3 may not include deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be 30% to 80%.

[0314] In another embodiment of the present invention, the heterocyclic compound represented by Formula 3 may not include deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be 50% to 70%.

[0315]

[0316] When a heterocyclic compound represented by Chemical Formula 1 and a heterocyclic compound represented by Chemical Formula 2, or a heterocyclic compound represented by Chemical Formula 1 and a heterocyclic compound represented by Chemical Formula 3 are included simultaneously, superior efficiency and lifespan effects are exhibited. From this, it can be expected that an exciplex phenomenon occurs when two compounds are included simultaneously.

[0317] The exciplex phenomenon described above is a phenomenon in which energy equivalent to the HOMO energy level of the donor (p-host) and the LUMO energy level of the acceptor (n-host) is emitted through electron exchange between two molecules. When the exciplex phenomenon occurs between two molecules, Reverse Intersystem Crossing (RISC) takes place, which can increase the internal quantum efficiency of the fluorescence up to 100%. When a donor (p-host) with good hole transport capability and an acceptor (n-host) with good electron transport capability are used as hosts in the emissive layer, holes are injected into the p-host and electrons are injected into the n-host, which allows for a reduction in the driving voltage and can help improve the lifespan. That is, when a heterocyclic compound represented by Chemical Formula 1 is used as the acceptor and a heterocyclic compound represented by Chemical Formula 2 or 3 is used as the donor, excellent device characteristics are exhibited.

[0318]

[0319] In one embodiment of the present invention, when the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 2 are simultaneously included, at least one of the compounds may not include deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be greater than 0%, greater than 1%, greater than 10%, greater than 20%, greater than 30%, greater than 40%, or greater than 50%, and may be less than 100%, less than 90%, less than 80%, less than 70%, or less than 60%.

[0320] In another embodiment of the present invention, at least one of the compounds may not include deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be 1% to 100%.

[0321] In another embodiment of the present invention, at least one of the compounds may not include deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be 20% to 90%.

[0322] In another embodiment of the present invention, at least one of the compounds may not include deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be 30% to 80%.

[0323] In another embodiment of the present invention, at least one of the compounds may not include deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be 50% to 70%.

[0324]

[0325] In one embodiment of the present invention, when the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 3 are simultaneously included, at least one of the compounds may not include deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be greater than 0%, greater than 1%, greater than 10%, greater than 20%, greater than 30%, greater than 40%, or greater than 50%, and may be less than 100%, less than 90%, less than 80%, less than 70%, or less than 60%.

[0326] In another embodiment of the present invention, at least one of the compounds may not include deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be 1% to 100%.

[0327] In another embodiment of the present invention, at least one of the compounds may not include deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be 20% to 90%.

[0328] In another embodiment of the present invention, at least one of the compounds may not include deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be 30% to 80%.

[0329] In another embodiment of the present invention, at least one of the compounds may not include deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be 50% to 70%.

[0330]

[0331] In one embodiment of the present invention, the heterocyclic compound represented by the chemical formula 2 may be represented by any one of the following compounds.

[0332]

[0333]

[0334]

[0335]

[0336]

[0337] In one embodiment of the present invention, the heterocyclic compound represented by the chemical formula 3 may be represented by any one of the following chemical formulas 3-1 to 3-6.

[0338] [Chemical Formula 3-1]

[0339]

[0340] [Chemical Formula 3-2]

[0341]

[0342] [Chemical Formula 3-3]

[0343]

[0344] [Chemical Formula 3-4]

[0345]

[0346] [Chemical Formula 3-5]

[0347]

[0348] [Chemical Formula 3-6]

[0349]

[0350] In the above chemical formulas 3-1 to 3-6,

[0351] The above R21, R22, Ar21, Ar22, L21, L22, e1, e2, f1 and f2 are identical to the definitions of Chemical Formula 3.

[0352]

[0353] In one embodiment of the present invention, the heterocyclic compound represented by the chemical formula 3 may be represented by any one of the following compounds.

[0354]

[0355]

[0356]

[0357]

[0358]

[0359] In addition, in one embodiment of the present invention, a composition for an organic layer is provided, comprising a heterocyclic compound represented by Formula 1, a heterocyclic compound represented by Formula 2, or a heterocyclic compound represented by Formula 3.

[0360] The specific details regarding the heterocyclic compound represented by Chemical Formula 1, the heterocyclic compound represented by Chemical Formula 2, and the heterocyclic compound represented by Chemical Formula 3 are the same as those described above.

[0361]

[0362] In one embodiment of the present invention, the weight ratio of the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 2 or the heterocyclic compound represented by Formula 3 in the composition for the organic layer may be 1:9 to 9:1, 1:9 to 5:5, or 2:8 to 5:5, but is not limited thereto.

[0363] In another embodiment of the present invention, the weight ratio of the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 2 in the composition for the organic layer may be 1:9 to 9:1, 1:9 to 5:5, or 2:8 to 5:5, but is not limited thereto.

[0364] In another embodiment of the present invention, the weight ratio of the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 3 in the composition for the organic layer may be 1:9 to 9:1, 1:9 to 5:5, or 2:8 to 5:5, but is not limited thereto.

[0365]

[0366] The above composition for the organic layer can be used when forming the organic material of an organic light-emitting device, and in particular, it can be used more preferably when forming the host of the light-emitting layer.

[0367]

[0368] In one embodiment of the present invention, the organic layer comprises a heterocyclic compound represented by Formula 1 and a heterocyclic compound represented by Formula 2, and can be used together with a phosphorescent dopant.

[0369] In another embodiment of the present invention, the organic layer comprises a heterocyclic compound represented by Formula 1 and a heterocyclic compound represented by Formula 3, and can be used together with a phosphorescent dopant.

[0370]

[0371] As the above phosphorescent dopant material, materials known in the art may be used. For example, phosphorescent dopant materials represented as LL'MX', LL'L"M, LMX'X", L2MX', and L3M may be used, but the scope of the present invention is not limited by these examples.

[0372] The above M can be iridium, platinum, osmium, etc.

[0373] The above L is sp 2X is an anionic dulocate ligand coordinated to M by carbon and heteroatoms, and 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.

[0374] Specific examples of the above-mentioned phosphorescent dopants are shown below, but are not limited to these examples.

[0375]

[0376]

[0377] In one embodiment of the present invention, the organic layer comprises a heterocyclic compound represented by Formula 1 and a heterocyclic compound represented by Formula 2, and can be used together with an iridium-based dopant.

[0378] In another embodiment of the present invention, the organic layer comprises a heterocyclic compound represented by Formula 1 and a heterocyclic compound represented by Formula 3, and can be used together with an iridium-based dopant.

[0379]

[0380] In one embodiment of the present invention, the iridium-based dopant may be (piq)2(Ir)(acac) as a red phosphorescent dopant or Ir(ppy)3 as a green phosphorescent dopant.

[0381]

[0382] 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.

[0383]

[0384] In an organic light-emitting device according to one embodiment of the present invention, the organic layer comprises an electron injection layer or an electron transport layer, and the electron injection layer or the electron transport layer may comprise a heterocyclic compound represented by the chemical formula 1.

[0385] In an organic light-emitting device according to another embodiment of the present invention, the organic layer comprises an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer may comprise a heterocyclic compound represented by the chemical formula 1.

[0386] In an organic light-emitting device according to another embodiment, the organic layer comprises an electron transport layer, a light-emitting layer, or a hole-blocking layer, and the electron transport layer, the light-emitting layer, or the hole-blocking layer may comprise a heterocyclic compound represented by the chemical formula 1.

[0387] In an organic light-emitting device according to another embodiment, the organic layer comprises a light-emitting layer, and the light-emitting layer may comprise a heterocyclic compound represented by the chemical formula 1.

[0388] In an organic light-emitting device according to another embodiment, the organic layer comprises a light-emitting layer, and the light-emitting layer may comprise a heterocyclic compound represented by Formula 1, a heterocyclic compound represented by Formula 2, or a heterocyclic compound represented by Formula 3.

[0389] In an organic light-emitting device according to another embodiment, the organic layer comprises a light-emitting layer, the light-emitting layer comprises a host material, and the host material may comprise a heterocyclic compound represented by the chemical formula 1.

[0390] In an organic light-emitting device according to another embodiment, the light-emitting layer may include two or more host materials, at least one of the host materials may include a heterocyclic compound represented by Chemical Formula 1, and the other may include a heterocyclic compound represented by Chemical Formula 2.

[0391] In an organic light-emitting device according to another embodiment, the light-emitting layer may include two or more host materials, at least one of the host materials may include a heterocyclic compound represented by Chemical Formula 1, and the other may include a heterocyclic compound represented by Chemical Formula 3.

[0392] In an organic light-emitting device according to another embodiment, the light-emitting layer may be used by pre-mixing two or more host materials, and at least one of the two or more host materials may include a heterocyclic compound represented by Chemical Formula 1, and the other may include a heterocyclic compound represented by Chemical Formula 2.

[0393] In an organic light-emitting device according to another embodiment, the light-emitting layer may be used by pre-mixing two or more host materials, and at least one of the two or more host materials may include a heterocyclic compound represented by Chemical Formula 1, and the other may include a heterocyclic compound represented by Chemical Formula 3.

[0394] The above pre-mixed means mixing the materials first and placing them in a single container to mix them before depositing two or more host materials onto an organic layer.

[0395]

[0396] An organic light-emitting device according to one embodiment of the present invention may further include one or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

[0397]

[0398] FIGS. 1 to 3 illustrate the stacking order of electrodes and organic layers of an organic light-emitting device according to an embodiment of the present invention. However, the scope of the present application is not intended to be limited by these figures, and structures of organic light-emitting devices known in the art may also be applied to the present application.

[0399] According to FIG. 1, an organic light-emitting device is shown in which an anode (200), an organic layer (300), and a cathode (400) are sequentially stacked on a substrate (100). However, the structure is not limited to this, and an organic light-emitting device in which a cathode, an organic layer, and an anode are sequentially stacked on a substrate may be implemented as shown in FIG. 2.

[0400] FIG. 3 illustrates a case where the organic layer is multilayer. 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 stacked structure, and, if necessary, the remaining layers excluding the light-emitting layer may be omitted, or other necessary functional layers may be added.

[0401]

[0402] In one embodiment of the present invention,

[0403] Step of preparing the substrate;

[0404] A step of forming a first electrode on the substrate;

[0405] A step of forming one or more organic layers on the first electrode; and

[0406] A method for manufacturing an organic light-emitting device comprising the step of forming a second electrode on one or more organic layers; wherein the step of forming one or more organic layers comprises the step of forming one or more organic layers using a composition for an organic layer according to an embodiment of the present invention.

[0407]

[0408] In one embodiment of the present invention, the step of forming the organic layer may be to pre-mix the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 2, or the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 3, and to form the layer using a thermal vacuum deposition method.

[0409] The above pre-mixed means mixing the materials first and placing them in a single source to mix the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2, or the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 3, before depositing them onto an organic layer.

[0410] The pre-mixed material may be referred to as a composition for an organic layer according to one embodiment of the present application.

[0411] The organic layer containing the heterocyclic compound represented by the above chemical formula 1 may additionally include other materials as needed.

[0412] The organic layer containing the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2 simultaneously may additionally include other substances as needed.

[0413] The organic layer containing the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 3 simultaneously may additionally include other materials as needed.

[0414]

[0415] In an organic light-emitting device according to one embodiment of the present invention, materials other than the heterocyclic compound represented by Formula 1, the heterocyclic compound represented by Formula 2, or the heterocyclic compound represented by Formula 3 are exemplified below, but these are for illustrative purposes only and are not intended to limit the scope of the present application and may be replaced with materials known in the art.

[0416]

[0417] Materials with a relatively large work function can be used as anode materials, and transparent conductive oxides, metals, or conductive polymers can be used. Specific examples of the above anode materials include 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, but are not limited thereto.

[0418]

[0419] Materials with a relatively low work function can be used as cathode materials, and metals, metal oxides, or conductive polymers can be used. Specific examples of the above cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer structural materials such as LiF / Al or LiO2 / Al, but are not limited thereto.

[0420]

[0421] As the hole injection layer material, known hole injection layer materials may be used, for example, phthalocyanine compounds such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429, or starburst-type amine derivatives described in the document [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), or polyaniline / dodecylbenzenesulfonic acid, which is a soluble conductive polymer. Poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate), polyaniline / camphor sulfonic acid, or polyaniline / poly(4-styrenesulfonate) can be used.

[0422]

[0423] Pyrazolin derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, etc., may be used as hole transport layer materials, and low molecular weight or high molecular weight materials may also be used.

[0424]

[0425] As electron transport layer materials, metal complexes of oxadiazole derivatives, anthraquinodimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinodimethane and its derivatives, fluorenone derivatives, diphenyldicyanoethylene and its derivatives, diphenoquinone derivatives, 8-hydroxyquinoline and its derivatives, etc., may be used, and not only low molecular weight materials but also high molecular weight materials may be used.

[0426]

[0427] For example, LiF is commonly used in the industry as an electron injection layer material, but the present application is not limited thereto.

[0428]

[0429] As the light-emitting layer material, red, green, or blue light-emitting materials may be used, and if necessary, two or more light-emitting materials may be mixed and used. In this case, two or more light-emitting materials may be deposited and used as individual sources, or they may be pre-mixed and deposited as a single source. Additionally, fluorescent materials may be used as the light-emitting layer material, but phosphorescent materials may also be used. As the light-emitting layer material, a material that emits light by combining holes and electrons injected from the anode and cathode, respectively, may be used alone, but materials in which a host material and a dopant material participate in light emission together may also be used.

[0430]

[0431] When using a mixture of hosts for the light-emitting layer material, hosts of the same series may be mixed, or hosts of different series may be mixed. For example, two or more types of materials, such as n-type host materials or p-type host materials, may be selected and used as the host material for the light-emitting layer.

[0432]

[0433] An organic light-emitting device according to one embodiment of the present invention may be a front-emitting type, a back-emitting type, or a double-sided emitting type depending on the material used.

[0434]

[0435] A heterocyclic compound according to one embodiment of the present invention can operate in organic electronic devices, including organic solar cells, organic photosensitive materials, and organic transistors, on a principle similar to that applied to organic light-emitting devices.

[0436]

[0437] Hereinafter, preferred embodiments are presented to aid in understanding the present invention, but the following embodiments are provided only to facilitate a better understanding of the present invention and do not limit the present invention thereto.

[0438]

[0439] <Preparation Example>

[0440] Preparation Example 1. Preparation of Compound 1-9

[0441]

[0442] Preparation Example 1-1. Preparation of Compound P-3

[0443] 7-bromo-1-chlorodibenzo[b,d]furan (20g, 71.04mmol), phenylboronic acid (8.6g, 71.04mmol), Pd(PPh3)4 (2.5g, 2.13mmol) and K2CO3 (15g, 106.56mmol) were dissolved in 300mL of 1,4-dioxane and 50mL of water (H2O), and then stirred at a reaction temperature of 100℃ for 6 hours.

[0444] After the reaction was completed, the reaction solution was cooled to room temperature and the solvent was removed using a rotary evaporator. The concentrated solution was dissolved in an excess amount of methylene chloride, extracted with water, and the organic layer was dried with anhydrous MgSO4 and filtered using silica gel. Subsequently, the solvent was removed from the filtrate using a rotary evaporator, and the solution was recrystallized with ethylene acetate to obtain 7.8 g (yield 89%) of compound P-3, a white solid.

[0445]

[0446] Preparation Example 1-2. Preparation of Compound P-2

[0447] Compounds P-3 (17.8g, 63.87mmol), B2Pin2 (24g, 95.81mmol), Pd(dba)2 (1.8g, 3.19mmol), SPhos (3g, 6.38mmol) and KOAc (12.5g, 127.74mmol) were dissolved in 300mL of 1,4-dioxane and stirred at a reaction temperature of 100℃ for 5 hours.

[0448] After the reaction was completed, the reaction solution was cooled to room temperature and the solvent was removed using a rotary evaporator. The concentrated solution was dissolved in an excess amount of methylene chloride, extracted with water, and the organic layer was dried with anhydrous MgSO4 and filtered using silica gel. Subsequently, the solvent was removed from the filtrate using a rotary evaporator, and the solution was purified by column chromatography (methylene chloride:hexane (1:1 (v / v))) to obtain 15 g (yield 63%) of the white solid compound P-2.

[0449]

[0450] Preparation Example 1-3. Preparation of Compound P-1

[0451] Compound P-2 (15g, 40.54mmol), 2-chloro-4-(2-fluorophenyl)-6-phenyl-1,3,5-triazine (11.5g, 40.54mmol), Pd(PPh3)4 (1.4g, 1.22mmol), and K2CO3 (8.4g, 60.81mmol) were dissolved in 250mL of 1,4-dioxane and 50mL of water (H2O), and then stirred at a reaction temperature of 100℃ for 6 hours.

[0452] After the reaction was complete, the solution was cooled to room temperature, the precipitated solid was filtered, thoroughly washed with distilled water and acetone, and then dried. The dried solid was dissolved in excess chloroform and filtered using silica gel. Subsequently, the solvent was removed from the filtrate using a rotary evaporator, and the solution was recrystallized with toluene to obtain 16 g (yield 81%) of compound P-1, a white solid.

[0453]

[0454] Preparation Example 1-4. Preparation of Compound 1-9

[0455] Compound P-1 (16g, 32.51mmol), 9H-carbazole (5.4g, 32.51mmol), and Cs2CO3 (21g, 65.02mmol) were dissolved in 200mL of dimethylacetamide and stirred at 150℃ for 6 hours.

[0456] After the reaction was completed, the reaction solution was cooled to room temperature and the solvent was removed using a rotary evaporator. The concentrated solution was dissolved in an excess amount of methylene chloride, extracted with water, and the organic layer was dried with anhydrous MgSO4 and filtered using silica gel. Subsequently, the solvent was removed from the filtrate using a rotary evaporator, and the solution was recrystallized with chlorobenzene to obtain 6.3 g (yield 30%) of compound 1-9, a yellow solid.

[0457]

[0458] The target compounds of Table 1 below were synthesized by preparing them in the same manner as in Preparation Example 1, except that Compound A of Table 1 below was used instead of 7-bromo-1-chlorodibenzo[b,d]furan, Compound B of Table 1 below was used instead of phenylboronic acid, Compound C of Table 1 below was used instead of 2-chloro-4-(2-fluorophenyl)-6-phenyl-1,3,5-triazine, and Compound D of Table 1 below was used instead of 9H-carbazole. Yield refers to the yield of the final reaction.

[0459]

[0460]

[0461]

[0462]

[0463]

[0464]

[0465]

[0466]

[0467]

[0468]

[0469]

[0470]

[0471]

[0472]

[0473] Preparation Example 2. Preparation of Compound 1-222

[0474]

[0475]

[0476] Preparation Example 2-1. Preparation of Compound S-3

[0477] 2-bromo-7-chlorodibenzo[b,d]furan (20g, 71.04mmol), 9H-carbazole (12g, 71.04mmol), Pd(dba)2 (2.1g, 3.55mmol), XPhos (3.4g, 7.11mmol) and NaOtBu (13.5g, 142.08mmol) were dissolved in 250mL of toluene and stirred at a reaction temperature of 100℃ for 6 hours.

[0478] After the reaction was complete, the solution was cooled to room temperature and the solvent was removed using a rotary evaporator. The concentrated solution was dissolved in excess methylene chloride, extracted with water, and the organic layer was dried with anhydrous MgSO4 and filtered using silica gel. Subsequently, the solvent was removed from the filtrate using a rotary evaporator, and the solution was recrystallized with ethylene acetate to obtain 20 g (yield 77%) of compound S-3, a white solid.

[0479]

[0480] Preparation Example 2-2. Preparation of Compound S-2

[0481] Compounds S-3 (20g, 53.05mmol), B2Pin2 (20g, 79.58mmol), Pd(dba)2 (1.5g, 2.65mmol), SPhos (2.5g, 5.31mmol) and KOAc (10.4g, 106.11mmol) were dissolved in 350mL of 1,4-dioxane and stirred at a reaction temperature of 100℃ for 5 hours.

[0482] After the reaction was complete, the solution was cooled to room temperature and the solvent was removed using a rotary evaporator. The concentrated solution was dissolved in an excess amount of methylene chloride, extracted with water, and the organic layer was dried with anhydrous MgSO4 and filtered using silica gel. Subsequently, the solvent was removed from the filtrate using a rotary evaporator, and the solution was purified by column chromatography (methylene chloride:hexane (2:1 (v / v))) to obtain 19.5 g (yield 80%) of compound S-2, a white solid.

[0483]

[0484] Preparation Example 2-3. Preparation of Compound S-1

[0485] Compound S-2 (19.5g, 42.45mmol), 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-(2-fluorophenyl)-1,3,5-triazine (15.3g, 42.45mmol), Pd(PPh3)4 (1.5g, 1.27mmol), and K2CO3 (8.8g, 63.68mmol) were dissolved in 300mL of 1,4-dioxane and 50mL of water (H2O), and then stirred at a reaction temperature of 100℃ for 6 hours.

[0486] After the reaction was complete, the solution was cooled to room temperature, the precipitated solid was filtered, thoroughly washed with distilled water and acetone, and then dried. The dried solid was dissolved in excess xylene and filtered using silica gel. Subsequently, the solvent was removed from the filtrate using a rotary evaporator, and the solution was recrystallized with chlorobenzene to obtain 19.3 g (yield 69%) of compound S-1, a white solid.

[0487]

[0488] Preparation Example 2-4. Preparation of Compound 1-222

[0489] Compound S-1 (19.3g, 29.29mmol), 9H-carbazole (4.9g, 29.29mmol), and Cs2CO3 (19g, 58.58mmol) were dissolved in 250mL of dimethylacetamide and stirred at 150℃ for 12 hours.

[0490] After the reaction was completed, the reaction solution was cooled to room temperature and the solvent was removed using a rotary evaporator. The concentrated solution was dissolved in an excess amount of methylene chloride, extracted with water, and the organic layer was dried with anhydrous MgSO4 and filtered using silica gel. Subsequently, the solvent was removed from the filtrate using a rotary evaporator and recrystallized with toluene to obtain 6.1 g (yield 26%) of compound 1-222, a yellow solid.

[0491]

[0492] The target compounds of Table 2 below were synthesized by preparing them in the same manner as in Preparation Example 2, except that Compound E of Table 2 below was used instead of 2-bromo-7-chlorodibenzo[b,d]furan in Preparation Example 2, Compound F of Table 2 below was used instead of 9H-carbazole in Preparation Example 2-1, Compound G of Table 2 below was used instead of 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-(2-fluorophenyl)-1,3,5-triazine, and Compound H of Table 2 below was used instead of 9H-carbazole in Preparation Example 2-4. Yield refers to the yield of the final reaction.

[0493]

[0494]

[0495]

[0496]

[0497]

[0498]

[0499] The remaining compounds, excluding those listed in Preparation Examples 1 and 2, Table 1, and Table 2 above, were also prepared using the same method as described in the aforementioned Preparation Examples, and the synthesis results are shown in Tables 3 and 4 below. Table 3 below is 1 The values ​​are from H NMR (CDCl3, 400 MHz), and Table 4 below shows the values ​​from FD-mass spectrometry (FD-MS: Field desorption mass spectrometry).

[0500]

[0501] Compound number 1H NMR(CDCl3, 400MHz)1-97.16-7.18 (dd, 2H), 7.23 (t, 1H), 7.35 (d, 2H), 7.44 (dd, 1H), 7.50-7.52 (m, 4H), 7.55-7.57 (m, 5H), 7.62-7.63 (d, 2H), 7.68-7.70 (m, 4H), 7.71 (t, 1H), 7.80-7.81(m, 2H), 7.85 (d, 2H), 7.88 (s, 1H), 7.90-7.92 (dd, 1H)1-87.15-7.17 (m, 4H), 7.20 (dd, 1H), 7.23 (t, 1H), 7.29-7.30 (m, 3H), 7.35 (dd, 2H), 7.40-7.41 (m, 4H), 7.47 (t, 1H), 7.51-7.53 (m, 6H), 7.55 (s, 1H), 7.57-7.59 (m, 6H), 7.62-7.63 (d, 2H), 7.70 (d, 1H), 7.80-7.81(m, 3H), 7.85 (d, 2H), 7.89 (dd, 1H)1-219.15(1H, s), 8.93(2H, d), 8.55(1H, d), 8.18(1H, d), 8.12(3H, d), 8.04(1H, d), 7.94(1H, d), 7.88(2H, d), 7.82(2H, d), 7.81(1H, dd), 7.79(1H, d), 7.75(1H, d), 7.72(1H, dd), 7.71(1H, dd), 7.68(1H, s), 7.63 (1H, t), 7.62 (1H, t), 7.54 (1H, dd), 7.52 (2H, dd), 7.51 (3H, t), 7.5 (1H, d), 7.44 (1H, d), 7.41 (1H, d)1-248.55(1H, s), 8.12(1H, d), 7.95(1H, d), 7.94(1H, d), 7.93(1H, d), 7.87(1H, d), 7.79(1H, d), 7.77(1H, d), 7.75(2H, d), 7.68(1H, dd), 7.64(1H, d), 7.63(2H, d), 7.62(1H, dd), 7.55(1H, dd), 7.54(1H, s), 7.52 (2H, t), 7.51 (3H, t), 7.5 (1H, dd), 7.44 (1H, dd), 7.41 (1H, t), 7.38 (1H, d), 7.33 (1H, d), 7.29 (2H, d), 1.5 (s, 6H)1-268.55(1H, s), 8.12(1H, d), 7.95(2H, d), 7.94(1H, d), 7.93(1H, d), 7.87(1H, d), 7.79(1H, d), 7.77(1H, d), 7.75(4H, d), 7.68(3H, dd), 7.64(2H, d), 7.63(2H, d), 7.55(1H, dd), 7.54(1H, dd), 7.52(2H, s), 7.51 (3H, t), 7.5 (1H, t), 7.41 (1H, dd), 7.38 (1H, dd), 7.35 (2H, t), 7.33 (1H, d), 7.29 (1H, d), 7.28 (1H, d), 7.22 (3H, dd)1-288.55(1H, s), 8.24(1H, d), 8.12(1H, d), 7.94(1H, d), 7.85(1H, d), 7.81(1H, d), 7.79(1H, d), 7.75(1H, d), 7.7(2H, d), 7.68(1H, dd), 7.63(1H, d), 7.62(1H, d), 7.57(2H, dd), 7.54(1H, dd), 7.52(4H, s), 7.51 (5H, t), 7.5 (1H, t), 7.48 (3H, dd), 7.44 (1H, dd), 7.41 (2H, t), 7.38 (1H, d), 7.33 (1H, d), 7.29 (2H, d)1-378.55(1H, s), 8.28(2H, d), 7.94(1H, d), 7.87(1H, d), 7.79(3H, d), 7.77(1H, d), 7.75(2H, d), 7.7(1H, d), 7.69(1H, d), 7.68(1H, dd), 7.62(2H, d), 7.57(1H, d), 7.54(1H, dd), 7.52(2H, dd), 7.51(7H, s), 7.48 (2H, t), 7.44 (2H, t), 7.41 (3H, dd), 7.33 (1H, dd), 7.25 (1H, t)1-447.16 (t, 1H), 7.19-7.20 (m, 4H), 7.23 (d, 1H), 7.25-7.37 (m, 4H), 7.40 (dd, 2H), 7.47 (t, 1H), 7.51 (dd, 6H), 7.55-7.57 (m, 4H), 7.62-7.63 (d, 2H), 7.70 (d, 1H), 7.80-7.81(m, 3H), 7.89 (dd, 1H)1-468.55(1H, s), 8.12(1H, d), 7.95(1H, d), 7.94(1H, d), 7.89(1H, d), 7.81(2H, d), 7.79(1H, d), 7.75(1H, d), 7.72(2H, d), 7.71(2H, dd), 7.68(3H, d), 7.66(1H, d), 7.64(1H, dd), 7.63(1H, dd), 7.54(1H, s), 7.52 (2H, t), 7.51 (3H, t), 7.5 (1H, dd), 7.41 (1H, dd), 7.38 (1H, t), 7.33 (1H, d), 7.32 (1H, d), 7.29 (1H, d)1-498.55(1H, s), 8.12(1H, d), 7.95(2H, d), 7.94(1H, d), 7.89(1H, d), 7.79(1H, d), 7.75(3H, d), 7.68(1H, d), 7.66(1H, d), 7.64(2H, dd), 7.63(1H, d), 7.62(1H, d), 7.54(1H, dd), 7.52(2H, dd), 7.51(3H, s), 7.5 (1H, t), 7.44 (1H, t), 7.41 (1H, dd), 7.38 (1H, dd), 7.33 (1H, t), 7.32 (1H, d), 7.29 (1H, d), 7.25 (1H, d)1-597.15-7.17 (m, 2H), 7.22 (dd, 1H), 7.25-7.28 (m, 3H), 7.34 (dd, 2H), 7.47 (t, 1H), 7.50-7.53 (m, 4H), 7.57 (s, 1H), 7.60-7.65 (m, 2H), 7.70 (d, 2H), 7.72-7.73 (m, 4H), 7.80-7.81(m, 3H), 7.85 (d, 2H), 7.89 (dd, 2H), 7.92-7.95 (m, 3H), 8.12 (d, 1H), 8.45 (dd, 1H)1-707.16-7.18 (m, 2H), 7.25-7.28 (m, 3H), 7.37 (t, 1H), 7.40-7.42 (m, 4H), 7.47 (t, 2H), 7.50-7.53 (m, 4H), 7.58 (s, 2H), 7.60-7.62 (m, 2H), 7.70 (d, 2H), 7.72-7.73 (m, 4H), 7.85 (d, 2H), 7.89 (dd, 2H), 7.92-7.95 (m, 4H), 8.12 (d, 1H), 8.45 (dd, 1H)1-728.55(1H, s), 8.08(2H, d), 7.95(1H, d), 7.94(1H, d), 7.89(1H, d), 7.87(1H, d), 7.85(1H, d), 7.81(2H, d), 7.79(1H, d), 7.75(1H, dd), 7.72(3H, d), 7.71(1H, d), 7.68(1H, dd), 7.66(1H, dd), 7.64(1H, s), 7.54 (1H, t), 7.52 (2H, t), 7.51 (5H, dd), 7.41 (2H, dd), 7.38 (2H, t), 7.35 (1H, d), 7.33 (1H, d), 7.32 (1H, d)1-908.55(1H, s), 8.41(2H, d), 8.2(1H, d), 8.12(1H, d), 7.95(2H, d), 7.94(1H, d), 7.85(1H, d), 7.81(1H, d), 7.8(2H, d), 7.79(1H, dd), 7.75(1H, d), 7.68(1H, d), 7.64(1H, dd), 7.63(1H, dd), 7.58(2H, s), 7.54 (1H, t), 7.52 (4H, t), 7.51 (5H, dd), 7.5 (1H, dd), 7.41 (2H, t), 7.38 (1H, d), 7.33 (1H, d), 7.29 (1H, d)1-997.16 (t, 1H), 7.19-7.21 (m, 3H), 7.30 (dd, 2H), 7.35-7.40 (m, 4H), 7.45-7.47 (m, 4H), 7.50-7.55 (m, 3H), 7.60 (s, 1H), 7.57-7.59 (m, 4H), 7.65 (s, 1H), 7.72 (d, 2H), 7.79-7.81(m, 4H), 7.89 (s, 2H), 7.90-7.92 (m, 3H), 8.12 (d, 1H), 8.30 (dd, 1H), 8.45 (d, 1H), 8.72 (d, 1H)1-1017.18 (t, 1H), 7.25-7.28 (m, 3H), 7.36-7.39 (m, 4H), 7.40-7.44 (m, 4H), 7.47 (t, 1H), 7.50-7.53 (m, 4H), 7.60 (dd, 2H), 7.65-7.70 (m, 3H), 7.72-7.73 (m, 4H), 7.85 (d, 1H), 7.89 (dd, 1H), 7.95-8.00 (m, 4H), 8.12 (d, 1H), 8.45 (dd, 1H), 8.60 (d, 1H)1-1102.46 (s, 6H), 6.96 (d, 1H), 7.16 (t, 1H), 7.20 (t, 1H), 7.26-7.30 (m, 4H), 7.38-7.43 (m, 3H), 7.49-4.52 (m, 2H), 7.56 (s, 1H), 7.59-7.62 (m, 4H), 7.65-7.67 (m, 3H), 7.70 (dd, 1H), 7.75-7.80 (m, 3H), 8.01 (s, 1H), 8.20 (d, 1H), 8.55 (d, 1H), 8.80 (s, 2H)1-1228.55(2H, s), 8.28(1H, d), 8.12(2H, d), 8.09(1H, d), 7.95(1H, d), 7.94(2H, d), 7.81(1H, d), 7.79(1H, d), 7.75(1H, d), 7.72(1H, dd), 7.71(1H, d), 7.68(1H, d), 7.64(1H, dd), 7.63(2H, dd), 7.54(1H, s), 7.52 (2H, t), 7.51 (4H, t), 7.5 (2H, dd), 7.46 (1H, dd), 7.41 (1H, t), 7.33 (2H, d), 7.29 (2H, d), 7.25 (2H, d)1-1258.55(2H, s), 8.28(1H, d), 8.12(3H, d), 8.09(1H, d), 8.08(1H, d), 7.95(4H, d), 7.94(2H, d), 7.87(1H, d), 7.81(1H, d), 7.79(1H, dd), 7.75(1H, d), 7.72(1H, d), 7.71(1H, dd), 7.68(1H, dd), 7.64(1H, s), 7.63 (1H, t), 7.54 (3H, t), 7.52 (2H, dd), 7.51 (6H, dd), 7.5 (1H, t), 7.46 (1H, d), 7.41 (2H, d), 7.35 (1H, d)1-1408.55(2H, s), 8.28(1H, d), 8.18(1H, d), 8.12(1H, d), 8.09(1H, d), 7.94(2H, d), 7.89(1H, d), 7.87(1H, d), 7.81(1H, d), 7.79(4H, dd), 7.68(1H, d), 7.66(2H, d), 7.63(3H, dd), 7.62(1H, dd), 7.54(1H, s), 7.52 (2H, t), 7.51 (6H, t), 7.5 (1H, dd), 7.46 (1H, dd), 7.41 (2H, t), 7.38 (1H, d), 7.33 (2H, d), 7.32 (1H, d)1-1437.16 (t, 2H), 7.20 (dd, 2H), 7.25-7.29 (m, 3H), 7.31-7.35 (m, 4H), 7.40 (dd, 1H), 7.46 (dd, 2H), 7.50-7.53 (m, 4H), 7.58-7.62 (m, 4H), 7.70 (dd, 1H), 7.76 (s, 1H), 7.79 (dd, 2H), 7.91-7.94 (m, 4H), 8.03 (d, 1H), 8.19 (d, 2H), 8.55 (dd, 2H)1-1487.16-7.18 (m, 3H), 7.22 (t, 1H), 7.25-7.30 (m, 4H), 7.35-7.38 (m, 3H), 7.40-7.42 (m, 3H), 7.44 (s, 1H), 7.48-7.50 (m, 3H), 7.52-7.55 (m, 3H) 7.59 (dd, 2H), 7.61 (d, 2H),7.65-7.70 (m, 4H), 7.77 (t, 1H), 7.79-7.82 (m, 5H), 8.08 (d, 1H), 8.19 (dd, 1H), 8.55 (dd, 2H)1-1547.16 (td, 2H), 7.19(dd, 4H), 7.20-7.21 (m, 4H), 7.30-7.32 (m, 4H), 7.35 (dd, 2H), 7.41 (t, 1H), 7.46 (dd, 2H), 7.51-7.53 (m, 3H), 7.56-7.58 (m, 4H), 7.62-7.65 (m, 3H), 7.79 (d, 1H), 7.81-7.83 (m, 3H), 7.91-7.92 (m, 4H), 8.08 (d, 2H), 8.29 (d, 2H), 8.55 (d, 2H)1-1718.55(2H, s), 8.12(1H, d), 7.94(2H, d), 7.87(1H, d), 7.85(2H, d), 7.81(2H, d), 7.79(2H, d), 7.77(1H, d), 7.69(1H, d), 7.68(2H, dd), 7.63(1H, d), 7.54(2H, d), 7.52(4H, dd), 7.51(6H, dd), 7.5(1H, s), 7.41 (2H, t), 7.38 (2H, t), 7.33 (2H, dd), 7.29 (1H, dd), 7.25 (2H, t)1-1768.55(2H, s), 8.12(1H, d), 7.94(2H, d), 7.89(1H, d), 7.87(1H, d), 7.79(3H, d), 7.77(1H, d), 7.69(1H, d), 7.68(3H, d), 7.67(1H, dd), 7.66(1H, d), 7.63(2H, d), 7.54(1H, dd), 7.52(4H, dd), 7.51(5H, s), 7.5 (1H, t), 7.41 (2H, t), 7.38 (1H, dd), 7.33 (2H, dd), 7.32 (1H, t), 7.29 (1H, d), 7.25 (2H, d)1-1867.16 (t, 1H), 7.20-7.22 (m, 3H), 7.26-7.29 (m, 4H), 7.31-7.35 (m, 4H), 7.40 (dd, 1H), 7.46 (dd, 2H), 7.50-7.53 (m, 4H), 7.58-7.62 (m, 4H), 7.70 (dd, 1H), 7.76 (s, 1H), 7.79 (dd, 2H), 7.91-7.94 (m, 4H), 8.03 (d, 1H), 8.19 (d, 1H), 8.55 (dd, 1H)1-2007.11-7.15 (m, 3H), 7.19 (d, 1H), 7.21-7.23 (m, 4H), 7.26 (t, 1H), 7.30-7.33 (m, 4H), 7.38-7.41 (m, 3H), 7.45-7.47 (m, 3H), 7.49-4.52 (m, 2H), 7.56 (s, 1H), 7.59-7.62 (m, 4H), 7.65-7.67 (m, 3H), 7.70 (dd, 1H), 7.75-7.80 (m, 3H), 8.01 (s, 1H), 8.20 (d, 1H), 8.55 (d, 1H), 8.80 (d, 1H)1-2157.16 (t, 1H), 7.20-7.24 (m, 3H), 7.30-7.35 (m, 3H), 7.38 (dd, 2H), 7.40-7.41 (m, 2H), 7.45-7.47 (m, 4H), 7.55 (s, 1H), 7.61-7.63 (m, 4H), 7.72 (d, 2H), 7.79-7.81(m, 4H), 7.88 (d, 1H), 7.90-7.92 (m, 3H), 8.30 (dd, 1H), 8.39 (d, 1H), 8.45 (d, 1H),1-2887.16-7.18 (m, 2H), 7.25-7.27 (m, 3H), 7.35 (t, 1H), 7.40-7.42 (m, 4H), 7.46 (t, 2H), 7.50-7.53 (m, 4H), 7.60 (s, 1H), 7.62-7.65 (m, 2H), 7.70 (d, 1H), 7.72-7.73 (m, 4H), 7.85 (d, 1H), 7.89 (dd, 1H), 7.92-7.95 (m, 4H), 8.12 (d, 1H), 8.45 (dd, 1H)1-2927.15 (t, 1H), 7.22 (dd, 1H), 7.25-7.28 (m, 4H), 7.34 (dd, 1H), 7.47 (t, 1H), 7.50-7.53 (m, 4H), 7.57 (s, 1H), 7.60-7.65 (m, 2H), 7.70 (s, 1H), 7.72-7.73 (m, 4H), 7.80-7.81(m, 3H), 7.85 (d, 2H), 7.89 (dd, 2H), 7.92-7.95 (m, 3H), 8.12 (d, 1H), 8.45 (dd, 1H)1-3168.55(1H, s), 8.41(2H, d), 8.2(1H, d), 8.12(3H, d), 7.94(1H, d), 7.89(1H, d), 7.81(1H, d), 7.8(1H, d), 7.79(1H, d), 7.72(1H, dd), 7.71(1H, d), 7.68(1H, d), 7.66(1H, dd), 7.63(1H, dd), 7.58(2H, s), 7.54 (1H, t), 7.52 (2H, t), 7.51 (3H, dd), 7.5 (1H, dd), 7.41 (1H, t), 7.38 (1H, d), 7.33 (1H, d), 7.32 (1H, d)1-3398.55(1H, s), 8.45(1H, d), 8.28(1H, d), 8.18(1H, d), 8.12(1H, d), 8.09(1H, d), 8.04(1H, d), 8(1H, d), 7.98(3H, d), 7.94(2H, dd), 7.87(1H, d), 7.79(3H, d), 7.77(3H, dd), 7.69(1H, dd), 7.68(1H, s), 7.63 (1H, t), 7.54 (1H, t), 7.52 (5H, dd), 7.51 (8H, dd), 7.5 (2H, t), 7.46 (1H, d), 7.33 (1H, d), 7.29 (1H, d)1-3467.16 (td, 2H), 7.20 (d, 2H), 7.25-7.28 (m, 4H), 7.30-7.35 (m, 4H), 7.39-7.43 (m, 3H), 7.46 (d, 2H), 7.75 (d, 2H), 7.85 (dd, 2H), 7.91-7.93 (m, 5H), 7.95 (d, 2H), 7.99(d, 1H), 8.12 (s, 1H), 8.15 (s, 1H), 8.19 (d, 2H), 8.55 (d, 2H)1-3607.16 (t, 2H), 7.20-7.24 (m, 4H), 7.31-7.33 (m, 4H), 7.42-7.44 (m, 2H), 7.47-7.49 (m, 4H), 7.55 (s, 1H), 7.58-7.59 (m, 2H), 7.61-7.63 (m, 4H), 7.66-7.69 (m, 3H), 7.72 (d, 2H), 7.88 (d, 1H), 7.90-7.92 (m, 5H), 8.02 (d, 1H), 8.06 (dd, 1H), 8.19 (d, 1H), 8.24 (s, 1H), 8.29 (dd, 1H), 8.37 (d, 2H), 8.55 (dd, 2H),1-3717.16 (td, 1H), 7.20 (d, 2H), 7.25-7.28 (m, 4H), 7.30-7.35 (m, 4H), 7.39-7.43 (m, 3H), 7.46-7.50 (m, 4H), 7.75 (d, 2H), 7.85 (dd, 2H), 7.91-7.93 (m, 5H), 7.95 (d, 2H), 7.99(d, 1H), 8.12 (s, 1H), 8.15 (s, 1H), 8.19 (d, 1H), 8.55 (d, 1H)1-3777.16 (t, 1H), 7.20-7.23 (m, 4H) 7.28 (d, 4H), 7.30-7.35 (m, 4H), 7.39-7.43 (m, 4H), 7.46-7.50 (m, 4H), 7.75 (d, 2H), 7.85 (dd, 2H), 7.91-7.93 (m, 5H), 7.95 (d, 2H), 7.99(d, 1H), 8.15 (s, 1H), 8.19 (d, 1H), 8.55 (d, 1H)1-4027.20-7.23 (m, 4H) 7.28 (d, 2H), 7.30-7.35 (m, 3H), 7.46-7.50 (m, 4H), 7.75 (d, 2H), 7.85 (dd, 2H), 7.91-7.93 (m, 4H), 7.95 (d, 2H), 7.99(d, 1H), 8.15 (s, 1H),1-4107.16 (t, 1H), 7.20-7.24 (m, 3H), 7.30-7.35 (m, 3H), 7.38 (dd, 1H), 7.40-7.41 (m, 2H), 7.45-7.47 (m, 2H), 7.55 (s, 1H), 7.72 (d, 2H), 7.88 (d, 1H), 7.90-7.92 (m, 3H), 8.30 (dd, 1H), 8.39 (d, 1H), 8.45 (d, 1H),1-4127.16 (t, 1H), 7.20 (dd, 2H), 7.31-7.35 (m, 2H), 7.46 (dd, 1H), 7.50-7.53 (m, 4H), 7.58-7.62 (m, 3H), 7.70 (dd, 1H), 7.79 (dd, 2H), 7.91-7.94 (m, 2H), 8.03 (d, 1H), 8.19 (d, 1H), 8.55 (dd, 1H)1-4237.21-7.25 (m, 2H), 7.30 (dd, 1H), 7.35-7.40 (m, 3H), 7.45 (d, 2H), 7.47-7.50 (m, 3H), 7.55 (s, 1H), 7.59-7.61 (m, 3H), 7.57-7.59 (m, 2H), 7.79-7.81(m, 3H),1-428100% 중수소 치환으로 수소 peak 관찰되지 않음1-4347.41-7.46 (m, 4H), 7.60 (td, 2H), 7.79 (dd, 2H), 7.96 (dd, 2H)1-4467.39-7.42 (m, 3H), 7.55 (s, 1H), 7.60 (t, 1H), 7.63 (dd, 2H), 7.80 (dd, 2H), 8.06 (s, 1H), 8.16 (d, 1H)1-4508.55(1H, s), 8.28(1H, d), 8.12(1H, d), 8.09(1H, d), 7.95(1H, d), 7.94(1H, d), 7.83(1H, d), 7.81(1H, d), 7.79(1H, d), 7.75(1H, dd), 7.72(1H, d), 7.71(1H, d), 7.68(1H, dd), 7.64(1H, dd), 7.63(1H, s), 7.54 (1H, t), 7.52 (2H, t), 7.51 (4H, dd), 7.5 (1H, dd), 7.46 (1H, t), 7.41 (1H, d), 7.33 (2H, d), 7.29 (1H, d)1-4547.46 (t, 2H), 7.80 (t, 2H), 7.91 (dd, 2H), 8.02 (dd, 2H)1-4607.16 (t, 1H), 7.19-7.21 (m, 3H), 7.30 (dd, 1H), 7.45-7.47 (m, 4H), 7.60 (s, 1H), 7.57-7.59 (m, 4H), 7.72 (d, 1H), 7.79-7.81(m, 3H), 7.89 (s, 1H), 8.12 (d, 1H), 8.30 (dd, 1H)1-4667.20 (dd, 1H), 7.31-7.35 (m, 2H), 7.46 (dd, 1H), 7.50-7.53 (m, 3H), 7.58-7.62 (m, 3H), 7.70 (dd, 1H), 7.79 (dd, 1H), 8.19 (d, 1H)1-4787.16 (t, 1H), 7.42-7.44 (m, 2H), 7.47-7.49 (m, 4H), 7.55 (s, 1H), 7.58-7.59 (m, 2H), 7.61-7.63 (m, 3H), 7.72 (d, 1H), 7.88 (d, 1H), 7.90-7.92 (m, 3H), 8.02 (d, 1H), 8.19 (d, 1H), 8.29 (dd, 1H), 8.37 (d, 2H), 8.55 (dd, 1H),1-4857.16 (t, 1H), 7.20-7.24 (m, 3H), 7.38 (dd, 1H), 7.55 (s, 1H), 7.61-7.63 (m, 4H), 7.66-7.69 (m, 3H), 7.72 (d, 1H), 7.88 (d, 1H), 8.06 (dd, 1H), 8.29 (dd, 1H),1-4987.16-7.20 (m, 4H), 7.35 (t, 2H), 7.46-7.49 (m, 4H), 7.56 (dd, 2H), 7.90 (td, 2H), 7.91-7.93 (m, 4H), 8.00 (dd, 2H), 8.20 (d, 2H), 8.54 (d, 2H)1-5027.31-7.33 (m, 3H), 7.36-7.37 (dd, 2H), 7.42-7.44 (m, 2H), 7.55 (s, 1H), 7.58-7.59 (m, 4H), 7.66-7.69 (m, 3H), 7.72 (s, 1H), 7.79-7.81(m, 3H), 7.88 (d, 2H), 8.29 (dd, 1H), 8.55 (dd, 2H)1-5428.28(2H, s), 7.95(1H, d), 7.89(1H, d), 7.79(1H, d), 7.75(3H, d), 7.68(1H, d), 7.66(1H, d), 7.64(1H, d), 7.62(2H, d), 7.54(1H, dd), 7.51(3H, d), 7.44(2H, d), 7.41(1H, dd), 7.38(1H, dd), 7.32(1H, s)1-5637.95(2H, s), 7.79(4H, d), 7.75(4H, d), 7.64(2H, d), 7.62(2H, d), 7.51(4H, d), 7.44(2H, d), 7.41(2H, d)1-5968.55(1H, s), 8.41(2H, d), 8.2(1H, d), 8.12(1H, d), 7.94(1H, d), 7.8(1H, d), 7.79(1H, d), 7.68(1H, d), 7.63(1H, d), 7.58(2H, dd), 7.54(1H, d), 7.52(2H, d), 7.51(3H, dd), 7.5(1H, dd), 7.41(1H, s), 7.33 (1H, t), 7.29 (1H, t), 7.25 (1H, dd)1-6027.81(1H, s), 7.79(2H, d), 7.75(1H, d), 7.72(1H, d), 7.71(1H, d), 7.68(2H, d), 7.62(1H, d), 7.54(2H, d), 7.52(2H, d), 7.51(4H, dd), 7.44(1H, d), 7.41(1H, d)1-6128.55(2H, s), 8.12(1H, d), 7.94(2H, d), 7.87(1H, d), 7.79(2H, d), 7.77(1H, d), 7.69(1H, d), 7.68(2H, d), 7.63(1H, d), 7.54(2H, dd), 7.52(2H, d), 7.51(4H, d), 7.5(1H, dd), 7.41(1H, dd), 7.33(2H, s), 7.29 (1H, t), 7.25 (2H, t)1-6301H, s), 8.09(1H, d), 7.95(1H, d), 7.81(1H, d), 7.79(1H, d), 7.75(1H, d), 7.72(1H, d), 7.71(1H, d), 7.68(1H, d), 7.64(1H, dd), 7.54(1H, d), 7.52(2H, d), 7.51(4H, dd), 7.46(1H, dd), 7.41(1H, s)1-6458.55(1H, s), 8.45(1H, d), 8.28(2H, d), 8.12(1H, d), 7.98(1H, d), 7.96(1H, d), 7.94(1H, d), 7.88(1H, d), 7.75(2H, d), 7.74(1H, dd), 7.63(1H, d), 7.52(5H, d), 7.51(6H, dd), 7.5(2H, dd), 7.41(4H, s), 7.33 (3H, t)1-6557.95(1H, s), 7.85(1H, d), 7.81(1H, d), 7.79(1H, d), 7.75(3H, d), 7.68(1H, d), 7.64(1H, d), 7.57(1H, d), 7.54(1H, d), 7.52(2H, dd), 7.51(5H, d), 7.41(2H, d), 7.4(1H, dd), 7.38(1H, dd), 7.19(2H, s)1-2227.35-7.39 (m, 4H), 7.42-7.45 (m, 3H), 7.50 (dd, 1H), 7.55-7.59 (m, 4H), 7.61 (s, 1H), 7.65-7.69 (m, 3H), 7.70-7.72 (m, 3H), 7.76 (s, 1H), 7.80-7.82 (m, 4H), 7.85 (dd, 1H), 7.90-7.93 (m, 3H), 8.01-8.05 (m, 5H), 8.19 (d, 1H), 8.55 (dd, 1H)1-2378.55(2H, s), 8.28(2H, d), 8.12(1H, d), 7.94(2H, d), 7.87(1H, d), 7.79(1H, d), 7.77(1H, d), 7.75(1H, d), 7.69(1H, d), 7.68(1H, dd), 7.66(1H, d), 7.63(1H, d), 7.62(1H, dd), 7.54(1H, dd), 7.52(2H, s), 7.51 (5H, t), 7.5 (1H, t), 7.44 (2H, dd), 7.41 (2H, dd), 7.38 (1H, t), 7.33 (2H, d), 7.29 (1H, d), 7.25 (2H, d)1-2507.29-7.31 (m, 3H), 7.39 (td, 1H), 7.41-7.45 (m, 4H), 7.52-7.56 (m, 5H), 7.62 (s, 1H), 7.65-7.66 (m, 3H), 7.70-7.75 (m, 4H), 7.82-7.86 (m, 5H), 7.90-7.95 (m, 3H), 8.05 (dd, 1H), 8.21 (dd, 1H), 8.56 (dd, 1H), 8.61 (d, 1H)1-2567.21-7.25 (m, 4H), 7.30-7.36 (m, 5H), 7.39 (dd, 1H), 7.41 (td, 1H), 7.45-7.47 (m, 3H), 7.50-7.53 (m, 4H), 7.61-7.64 (m, 4H), 7.76 (s, 1H), 7.80-7.85 (m, 4H), 7.88 (dd, 2H), 7.90-7.94 (m, 3H), 8.04 (dd, 1H), 8.19 (dd, 1H), 8.55 (dd, 1H), 8.59 (d, 1H)1-2618.55(2H, s), 8.12(2H, d), 7.94(2H, d), 7.8(1H, d), 7.79(1H, d), 7.75(1H, d), 7.68(1H, d), 7.66(4H, d), 7.63(2H, d), 7.62(1H, dd), 7.54(1H, d), 7.52(4H, d), 7.51(5H, dd), 7.5(3H, dd), 7.44(1H, s), 7.41 (2H, t), 7.33 (2H, t), 7.29 (2H, dd), 7.25 (2H, dd)1-2717.29-7.31 (m, 4H), 7.32-7.35 (m, 3H), 7.41-7.45 (m, 4H), 7.49-7.50 (m, 3H), 7.52-7.56 (m, 5H), 7.65-7.66 (m, 4H), 7.70-7.75 (m, 4H), 7.78-7.81 (m, 3H), 7.83-7.86 (m, 5H), 7.90-7.95 (m, 3H), 8.05 (dd, 1H), 8.21 (dd, 1H), 8.56 (dd, 1H), 8.61 (d, 1H)1-2752.45 (s, 12H), 6.96 (dd, 2H), 7.16 (t, 1H), 7.20-7.22 (m, 3H), 7.31-7.35 (m, 2H), 7.40-7.43 (m, 4H), 7.46 (dd, 1H), 7.50-7.53 (m, 3H), 7.58-7.62 (m, 3H), 7.65-7.67 (m, 3H), 7.70 (dd, 1H), 7.79 (dd, 1H), 8.19 (d, 1H), 8.26 (dd, 2H), 8.30-8.34 (m, 3H), 8.55 (dd, 2H), 8.80 (s, 2H)1-3837.32-7.36 (m, 5H), 7.39-7.41 (m, 3H), 7.45 (t, 1H), 7.46-7.49 (m, 3H), 7.50 (dd, 1H), 7.55-7.58 (m, 4H), 7.60 (s, 1H), 7.65-7.69 (m, 3H), 7.70-7.72 (m, 4H), 7.79 (s, 1H), 7.80-7.82 (m, 4H), 7.86 (dd, 1H), 7.90-7.93 (m, 3H), 8.01-8.05 (m, 5H), 8.19 (d, 1H), 8.30-8.36 (m, 4H), 8.55 (dd, 1H)1-3987.34-7.36 (m, 3H), 7.42-7.46 (m, 5H), 7.50 (dd, 1H), 7.55-7.59 (m, 5H), 7.60 (s, 1H), 7.65-7.69 (m, 3H), 7.70-7.73 (m, 4H), 7.80-7.82 (m, 4H), 7.85 (dd, 1H), 7.90-7.93 (m, 3H), 8.01-8.05 (m, 4H), 8.19 (d, 1H), 8.55 (dd, 1H), 8.69 (d, 1H)1-4717.20 (dd, 1H), 7.31-7.34 (m, 4H), 7.46 (dd, 1H), 7.50-7.54 (m, 5H), 7.58-7.62 (m, 4H), 7.70 (s, 1H), 7.79 (dd, 1H), 8.19 (d, 1H)1-4967.16-7.19 (m, 4H), 7.25-7.28 (m, 3H), 7.36 (dd, 1H), 7.40-7.43 (m, 4H), 7.51 (dd, 1H), 7.61 (t, 1H), 7.72-7.75 (m, 3H), 8.08 (dd, 1H), 8.55 (d, 1H)1-5518.55(1H, s), 8.12(1H, d), 7.95(1H, d), 7.94(1H, d), 7.89(1H, d), 7.75(1H, d), 7.73(1H, d), 7.64(1H, d), 7.63(1H, d), 7.5(1H, dd), 7.44(1H, d), 7.33(1H, d), 7.29(1H, dd), 7.25(1H, dd)1-5608.55(1H, s), 8.28(2H, d), 8.12(1H, d), 7.94(1H, d), 7.89(1H, d), 7.79(1H, d), 7.69(1H, d), 7.68(1H, d), 7.66(2H, d), 7.63(1H, dd), 7.54(1H, d), 7.51(3H, d), 7.5(1H, dd), 7.41(1H, dd), 7.38(1H, s), 7.33 (1H, t), 7.32 (1H, t), 7.29 (1H, dd.

[0502]

[0503] Compound number FD-MS Compound number FD-MS1-8 m / z = 716.83 (C 51 H 32 N4O) 1-21 m / z = 790.91 (C 57 H 34 N4O) 1-24 m / z = 756.89 (C 54 H 36 N4O) 1-26 m / z = 879.01 (C 64 H 38 N4O) 1-28 m / z = 792.92 (C 57 H 36 N4O) 1-90 m / z = 822.97 (C 57 H 34 N4OS) 1-46 m / z = 730.l (C 51 H 30 N4O2) 1-49 m / z = 730.81 (C 51 H 30 N4O2) 1-9 m / z = 640.75 (C 45 H 28 N4O) 1-18 m / z = 867.02 (C 63 H 38 N4O) 1-37 m / z = 792.92 (C 57 H 36 N4O) 1-44 m / z = 730.83 (C 51 H 30 N4O2) 1-59 m / z = 806.93 (C 57 H 34 N4O2) 1-70 m / z = 806.93 (C 57 H 34 N4O2) 1-72 m / z = 806.91 (C 57 H 34 N4O2) 1-99 m / z = 899.08 (C 63 H 38 N4OS) 1-101 m / z = 805.l (C 57 H 35 N5O) 1-110 m / z = 882.02 (C 63 H 39 N5O) 1-122 m / z = 805.92 (C 57 H35 N5O)1-125m / z=882.02(C 63 H 39 N5O)1-140m / z=882.02(C 63 H 39 N5O)1-143m / z=805.94(C 57 H 35 N5O)1-148m / z=882.04(C 63 H 39 N5O)1-154m / z=958.14(C 69 H 43 N5O)1-171m / z=882.02(C 63 H 39 N5O)1-176m / z=882.02(C 63 H 39 N5O)1-186m / z=806.93(C 57 H 34 N4O2)1-200m / z=899.08(C 63 H 38 N4OS)1-215m / z=835.98(C 57 H 33 N5OS)1-288m / z=732.90(C 51 H 32 N4OS)1-292m / z=732.90(C 51 H 32 N4OS)1-316m / z=746.88(C 51 H 30 N4OS)1-339m / z=974.18(C 69 H 43 N5S)1-346m / z=822.00(C 57 H 35 N5S)1-360m / z=974.20(C 69 H 43 N5S)1-371m / z=822.99(C 57 H 34 N4OS)1-377m / z=839.05(C 57 H 34 N4S2)1-402m / z=724.89(C 51 H 24 D8N4O)1-410m / z=725.90(C 51 H 23D9N4O)1-412m / z=727.91(C 51 H 21 D 11 N4O)1-423m / z=728.92(C 51 H 20 D 12 N4O)1-428m / z=668.92(C 45 D 28 N4O)1-434m / z=756.05(C 51 H9D 23 N4S)1-446m / z=830.09(C 57 H 11 D 24 N5O)1-450m / z=812.96(C 57 H 28 D7N5O)1-454m / z=833.11(C 57 H8D 27 N5O)1-460m / z=898.14(C 63 H 23 D 16 N5O)1-466m / z=763.99(C 51 H 12 D 17 N4OS)1-478m / z=752.92(C 51 H 24 D6N4OS)1-485m / z=852.08(C 57 H 17 D 16 N5OS)1-498m / z=909.10(C 63 H 24 D 13 N5O2)1-502m / z=804.36(C 57 H 24 D 14 N4O)1-542m / z=738.29(C 51 H 22 D8N4O2)1-563m / z=818.34(C 57 H 22 D 12 N4O2)1-596m / z=833.34(C 57 H 23 D 12 N5S)1-602m / z=821.38(C 57 H 19 D 16N5O)1-612m / z=892.38(C 63 H 28 D 11 N5O)1-630m / z=821.38(C 57 H 19 D 16 N5O)1-645m / z=732.89(C 51 H 32 N4S)1-655m / z=1057.35(C 75 H 24 D 23 N5O)1-222m / z=805.94(C 57 H 35 N5O)1-237m / z=805.92(C 57 H 35 N5O)1-250m / z=819.92(C 57 H 33 N5O2)1-256m / z=912.08(C 63 H 37 N5OS)1-261m / z=882.02(C 63 H 39 N5O)1-271m / z=971.14(C 69 H 42 N6O)1-275m / z=951.15(C 67 H 46 N6O)1-383m / z=898.10(C 63 H 39 N5S)1-398m / z=928.14(C 63 H 37 N5S2)1-471m / z=823.04(C 57 H 18 D 17 N5O)1-496m / z=1074.40(C 75 H 19 D 27 N6O)1-551m / z=746.36(C 51 H 14 D 17 N5O)1-560m / z=817.36(C 57 H 23 D 12 N5O)

[0504]

[0505] Preparation 3. Compound 2-2's preparation

[0506]

[0507]

[0508] Preparation Example 3-1. Preparation of Compound R-1

[0509] 9H,9'H-3,3'-bicarbazole (20g, 60.16mmol), bromobenzene (9.4g, 60.16mmol), Pd2(dba)3 (5.5g, 6.02mmol), XPhos (5.7g, 12.03mmol) and K2CO3 (12.5g, 90.24mmol) were dissolved in 300mL of 1,4-dioxane and stirred at a reaction temperature of 100℃ for 6 hours.

[0510] After the reaction was complete, the solution was cooled to room temperature and the solvent was removed using a rotary evaporator. The concentrated solution was dissolved in an excess amount of methylene chloride, extracted with water, and the organic layer was dried with anhydrous MgSO4 and filtered using silica gel. Subsequently, the solvent was removed from the filtrate using a rotary evaporator, and the solution was recrystallized with ethylene acetate to obtain 20 g (yield 81%) of compound R-1, a white solid.

[0511]

[0512] Preparation Example 3-2. Preparation of Compound 2-2

[0513] Compound R-1 (20g, 49.02mmol), 4-bromo-1,1'-biphenyl (12g, 49.02mmol), Pd2(dba)3 (4.5g, 4.9mmol), P(tBu)3 (1.9g, 9.81mmol) and NaOtBu (9.5g, 98.04mmol) were dissolved in 300mL of toluene and stirred at a reaction temperature of 100℃ for 15 hours.

[0514] After the reaction was complete, the solution was cooled to room temperature and the solvent was removed using a rotary evaporator. The concentrated solution was dissolved in excess methylene chloride, extracted with water, and the organic layer was dried with anhydrous MgSO4 and filtered using silica gel. Subsequently, the solvent was removed from the filtrate using a rotary evaporator, and the solution was recrystallized with chlorobenzene to obtain 17 g (yield 63%) of compound 2-2, a white solid.

[0515]

[0516] The target compounds of Table 5 below were synthesized by preparing them in the same manner as in Preparation Example 3, except that compound a of Table 5 below was used instead of 9H,9'H-3,3'-bicarbazole, compound b of Table 5 below was used instead of bromobenzene, and compound c of Table 5 below was used instead of 4-bromo-1,1'-biphenyl. Yield refers to the yield of the final reaction.

[0517]

[0518]

[0519]

[0520]

[0521] Preparation Example 4. Preparation of Compound 2-42

[0522]

[0523] 9-([1,1'-biphenyl]-4-yl)-9'-phenyl-9H,9'H-3,3'-bicarbazole) (20g, 35.74mmol) was dissolved in 200mL of D6-benzene, and then triflic acid (22mL, 250.18mmol) was slowly added. The reaction temperature was raised to 60℃ and stirred for 1 hour, after which a solution of triethylamine (35mL, 250.18mmol) dissolved in 50mL of D2O was added to neutralize the mixture.

[0524] Extraction was performed by adding an excess amount of ethyl acetate, and the organic layer was dried with anhydrous MgSO4 and filtered using silica gel. The solvent was removed from the filtrate using a rotary evaporator to obtain 19 g of compound 2-42, a white solid (yield 92%, 100% D-substitution rate).

[0525]

[0526] The target compound of Table 6 below was synthesized by preparing it in the same manner as in Preparation Example 4, except that compound d of Table 6 below was used instead of 9-([1,1'-biphenyl]-4-yl)-9'-phenyl-9H,9'H-3,3'-bicarbazole in Preparation Example 4 above. Yield refers to the yield of the final reaction.

[0527]

[0528]

[0529]

[0530]

[0531]

[0532] The remaining compounds, excluding those listed in Preparation Examples 3 and 4, Table 5, and Table 6 above, were also prepared using the same method as described in the aforementioned Preparation Examples, and the synthesis results are shown in Tables 7 and 8 below. Table 7 below is 1 The values ​​are from H NMR (CDCl3, 300 MHz), and Table 8 below shows the values ​​from FD-mass spectrometry (FD-MS: Field desorption mass spectrometry).

[0533]

[0534] Compound number 1H NMR(CDCl3, 300MHz)2-27.20-7.24 (m, 4H), 7.30-7.33 (m, 5H), 7.41-7.42 (m, 3H), 7.75 (dd, 2H), 7.89 (s, 2H), 7.94-7.96 (m, 4H), 8.00-8.03 (m, 2H), 8.11 (d, 2H), 8.19 (d, 1H), 8.30 (d, 1H), 8.55 (dd, 2H)2-47.21-7.23 (m, 3H), 7.30-7.33 (m, 6H), 7.38 (s, 1H), 7.41-7.43 (m, 4H), 7.75 (dd, 2H), 7.87-7.90 (m, 4H), 7.94-7.96 (m, 4H), 8.00-8.03 (m, 2H), 8.11 (d, 2H), 8.19 (d, 1H), 8.30 (d, 1H), 8.55 (dd, 2H)2-157.19-7.21 (m, 5H), 7.25-7.27 (m, 3H), 7.30-7.33 (m, 6H), 7.38 (s, 1H), 7.41-7.43 (m, 4H), 7.75 (dd, 2H), 7.87-7.90 (m, 4H), 7.94-7.96 (m, 4H), 8.00-8.03 (m, 2H), 8.11 (d, 2H), 8.19 (d, 1H), 8.30 (d, 1H), 8.55 (dd, 2H)2-317.19-7.21 (m, 3H), 7.23-7.25 (m, 3H), 7.30-7.32 (m, 6H), 7.41-7.43 (m, 4H), 7.75 (dd, 2H), 7.87-7.90 (m, 4H), 7.94-7.96 (m, 4H), 8.00-8.03 (m, 2H), 8.11 (d, 2H), 8.19 (d, 1H), 8.25 (s, 1H), 8.30 (d, 1H), 8.55 (dd, 2H)3-67.16 (t, 2H), 7.23-7.26 (m, 3H), 7.35-7.37 (m, 4H), 7.40-7.41 (m, 5H), 7.49 (dd, 2H), 7.65 (dd, 2H), 7.75 (d, 2H), 7.91-7.95 (m, 4H), 7.99 (dd, 2H), 8.56 (dd, 2H)3-277.19 (t, 2H), 7.20-7.21 (m, 4H), 7.23-7.26 (m, 3H), 7.35-7.37 (m, 4H), 7.40-7.41 (m, 5H), 7.49 (dd, 2H), 7.65 (dd, 2H), 7.75 (d, 2H), 7.91-7.95 (m, 4H), 7.99 (dd, 2H), 8.56 (dd, 2H)3-377.16 (t, 2H), 7.23-7.26 (m, 3H), 7.35-7.37 (m, 4H), 7.40-7.41 (m, 5H), 7.49 (dd, 2H), 7.65 (dd, 2H), 7.75 (d, 2H), 7.81 (s, 1H), 7.91-7.95 (m, 3H), 7.99 (dd, 2H), 8.56 (dd, 2H)2-427.50 (s, 1H)2-477.55 (s, 1H), 8.01 (s, 1H)2-51 with a deuterium substitution rate of 100%. 1 No H NMR peaks 2-558.32 (s, 1H), 8.66 (m, 1H)2-687.75 (d, 2H), 7.81 (s, 1H)3-43 with 100% deuterium substitution. 1 No H NMR peak3-537.26 (d, 2H), 7.39 (s, 1H), 8.26 (m, 2H)3-557.38 (s, 1H)3-647.38 (s, 1H), 7.55 (m, 2H), 8.03 (dd, 2H)3-718.11 (dd, 1H)3-757.59 (dd, 1H), 8.12 (m, 2H)

[0535]

[0536] Compound Number FD-MS Compound Number FD-MS2-2m / z=560.70(C 42 H 28 N2)2-4m / z=636.80(C 48 H 32 N2)2-15m / z=712.90(C 54 H 36 N2)2-31m / z=726.88(C 54 H 34 N2O)3-6m / z=560.70(C42 H 28 N2)3-27m / z=636.80(C 48 H 32 N2)3-37m / z=560.70(C 42 H 28 N2)2-42m / z=587.87(C 42 HD 27 N2)2-47m / z=662.94(C 48 H2D 28 N2)2-51m / z=659.40(C 48 H5D 25 N2)2-55m / z=668.98(C 48 D3H2N2)2-68m / z=746.08(C 54 H3D 33 N2)3-43m / z=746.10(C 54 H3D 33 N2)3-53m / z=663.95(C 48 H5D 27 N2)3-55m / z=663.96(C 48 HD 31 N2)3-64m / z=583.83(C 42 H5D 23 N2)3-71m / z=583.84(C 42 HD 27 N2)3-75m / z=587.87(C 42 H3D 25 N2)

[0537]

[0538] Experimental Example 1.

[0539] Experimental Example 1-1. Fabrication of an Organic Light-Emitting Device

[0540] A glass substrate coated with a thin film of ITO to a thickness of 1,500 Å was cleaned with distilled water ultrasonics. After cleaning with distilled water, the substrate was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UVO (Ultraviolet Ozone) using UV light for 5 minutes in a UV (Ultraviolet) cleaner. Subsequently, the substrate was transferred to a plasma cleaner (PT), and plasma treatment was performed under vacuum conditions to increase the ITO work function and remove residual film, after which it was transferred to a thermal evaporation equipment for organic deposition.

[0541] A common layer, a hole injection layer m-MTDATA (4,4',4''-Tris(N-3-methylphenyl-N-phenyl-amino)-triphenylamine) and a hole transport layer TCTA (Tris(4-carbazoyl-9-ylphenyl)amine) were formed on the above ITO transparent electrode (anode).

[0542] A light-emitting layer was deposited on top of it as follows. The light-emitting layer used the compound listed in Table 9 below as the host, and Ir(ppy)3 (tris(2-phenylpyridine)iridium) as the green phosphorescent dopant, and was deposited to a thickness of 360 Å by doping the host with 7% Ir(ppy)3.

[0543] Subsequently, BCP was deposited as a hole blocking layer with a thickness of 60 Å, and TmPyPB (1,3,5-Tri(m-pyridin-3-ylphenyl)benzene) was deposited as an electron transport layer with a thickness of 200 Å on top of it. Finally, lithium fluoride (LiF) was deposited on the electron transport layer with a thickness of 10 Å to form an electron injection layer, and then aluminum (Al) was deposited on the electron injection layer with a thickness of 1,200 Å to form a cathode, thereby fabricating an organic electroluminescent device.

[0544] Meanwhile, all organic compounds required for OLED device fabrication are 10 each for each material -6~10 -8 It was purified by vacuum sublimation under torr and used for fabricating OLEDs (Organic Light Emitting Devices).

[0545]

[0546] Experimental Example 1-2. Driving voltage and luminous efficiency of an organic light-emitting diode

[0547] The electroluminescence (EL) characteristics of the organic light-emitting diode fabricated as described above were measured using MaxScience's M7000, and based on the measurement results, the reference brightness was 6,000 cd / m² using a lifetime measurement device (M6000) manufactured by MaxScience 2 When, T 90 The driving voltage, luminous efficiency, color coordinates (CIE), and lifetime of the organic light-emitting diode manufactured according to the present invention were measured. The results of the measurements are shown in Table 9 below.

[0548] The above T 90 represents the lifespan (unit: hours) of the time it takes to reach 90% of the initial brightness.

[0549]

[0550] Compound driving voltage (V), luminous efficiency (cd / A), chromatic lifetime (T 90Comparative Example 1 ref. 15.68 30.5 Green 15 Comparative Example 2 ref. 25.50 25.7 Green 45 Comparative Example 3 ref. 35.55 25.5 Green 30 Comparative Example 4 ref. 45.59 27.6 Green 25 Comparative Example 5 ref. 55.66 33.2 Green 26 Example 11 - 49 4.18 50.9 Green 75 Example 21 - 18 4.42 49.5 Green 80 Example 31 - 21 4.58 48.8 Green 90 Example 41 - 24 4.44 47.8 Green 81 Example 51 - 26 4.12 49.9 Green 70 Example 61 - 28 5.01 51.2 Green 65 Example 71 - 37 4.38 46.7 Green 84 Example 81-444.1651.1 Green69 Example 91-594.2052.3 Green89 Example 101-704.2150.1 Green95 Example 111-724.1949.8 Green72 Example 121-904.3240.2 Green66 Example 131-994.2252.2 Green82 Example 141-1014.5245.7 Green99 Example 151-1104.3242.3 Green90 Example 161-1224.3352.6 Green77 Example 171-1254.4453.0 Green83 Example 181-1404.4051.9 Green70 Example 191-1434.2954.2Green97 Example 201-1484.2651.6Green101 Example 211-1544.2853.2Green74 Example 221-1714.5250.9Green91 Example 231-1764.5046.9Green89 Example 241-1864.1750.3Green78 Example 251-2004.2051.2Green86 Example 261-2154.5545.9Green109 Example 271-2884.2150.6Green96 Example 281-2924.1952.2Green92 Example 291-3164.2351.4Green88 Example 301-3394.5352.0Green76 Example 311-3464.3153.3Green100 Example 321-3604.4549.9Green96 Example 331-3714.2249.1Green80 Example 341-3774.2948.9Green84 Example 351-4024.1752.0 Green121 Example 361-4104.1853.4 Green116 Example 371-4124.1950.6 Green108 Example 381-4234.2351.1 Green120 Example 391-4284.2152.2 Green108 Example 401-4344.2451.7 Green113 Example 411-4464.3048.7 Green128 Example 421-4504.4551.1 Green77 Example 431-4544.3854.0 Green123 Example 441-4604.3549.9 Green115 Example 451-4664.2050.2 Green103 Example 461-4784.2152.0 Green92 Example 471-4854.5546.4 Green138 Example 481-4984.3653.6 Green103 Example 491-5024.1950.5 Green116 Example 501-5424.2251.2 Green98 Example 511-5634.1649.9 Green101 Example 521-5964.5548.2 Green111 Example 531-6024.4245.3 Green121 Example 541-6124.4544.8 Green115 Example 551-6304.5543.6Green122 Example 561-6454.5242.3Green105 Example 571-6554.6146.8Green120 Example 581-2224.5045.1Green116 Example 591-2374.5146.4Green120 Example 601-2504.5344.8Green119 Example 611-2564.4946.0Green108 Example 621-2614.6045.3Green115 Example 631-2714.6244.9Green117 Example Example 641-2754.6144.7Green125 Example 651-3834.5245.2Green122 Example 661-3984.5046.1Green104 Example 671-4714.4845.5Green139 Example 681-4964.6048.8Green141 Example 691-5514.5945.4Green126 Example 701-5604.6343.8Green124.

[0551]

[0552] [Comparative Example Compound]

[0553]

[0554]

[0555] As shown in the results of Table 9 above, an organic light-emitting device comprising a heterocyclic compound represented by Formula 1 of the present invention in an organic layer exhibited excellent luminous efficiency and lifetime as the triazine group and the carbazole group were bonded to the ortho position of phenylene, and the triazine group was directly bonded to the heteroaryl group containing an aryl group. When the triazine group and the carbazole group are bonded to the ortho position, they induce spatial charge transfer, which can result in higher luminous efficiency characteristics than compounds bonded to the para or meta position. Furthermore, the heteroaryl group containing an aryl group directly bonded to the triazine group can stabilize the LUMO, thereby exhibiting excellent lifetime characteristics.

[0556] On the other hand, the driving voltage of the organic light-emitting device containing the compound of the above comparative example in the organic layer was higher than that of the example, while the luminous efficiency and lifespan were lower than those of the example.

[0557] The compounds of Comparative Examples 1 to 3 have triazine and carbazole groups bonded to the ortho positions of phenylene, but the dibenzofuranyl group does not contain substituents, resulting in an unstable LUMO of the triazine group, high driving voltage, and low luminous efficiency and lifetime characteristics. The compound of Comparative Example 4 has triazine and carbazole groups bonded to the para positions of phenylene, and the dibenzofuranyl group does not contain substituents. The para positions fail to induce spatial charge transfer, and the dibenzofuranyl group lacks substituents, resulting in an unstable LUMO, high driving voltage, and low luminous efficiency and lifetime characteristics. The compound of Comparative Example 5 has a triazine group connected to a heteroaryl group containing an aryl group via a phenylene linker, resulting in an unstable LUMO and very low lifetime characteristics.

[0558]

[0559] Experimental Example 2.

[0560] An organic light-emitting device was manufactured in the same manner as Experimental Example 1-1 above, except that the light-emitting layer was prepared by pre-mixing one type of first host (compound of Chemical Formula 1) and one type of second host (compound of Chemical Formula 2 or Chemical Formula 3) listed in Table 10 below and then depositing them from a single source.

[0561]

[0562] Experimental Example 2-2. Driving voltage and luminous efficiency of an organic light-emitting diode

[0563] The electroluminescence (EL) characteristics of the organic light-emitting diode fabricated as described above were measured using MaxScience's M7000, and based on the measurement results, the reference brightness was 6,000 cd / m² using a lifetime measurement device (M6000) manufactured by MaxScience 2 When, T 90 The driving voltage, luminous efficiency, color coordinates (CIE), and lifetime of the organic light-emitting diode manufactured according to the present invention were measured. The results of the measurements are shown in Table 10 below.

[0564] The above T 90 represents the lifespan (unit: hours) of the time it takes to reach 90% of the initial brightness.

[0565]

[0566] Compound Ratio (P:N) Driving Voltage (V) Luminous Efficiency (cd / A) Color Coordinates Lifetime (T90) p-Host n-Host Comparative Example 63-27 Ref.16: 44.58 38.5 Green 45 Comparative Example 72-2 Ref.26: 45.00 36.7 Green 85 Comparative Example 82-68 Ref.36: 45.05 36.0 Green 60 Comparative Example 93-71 Ref.46: 44.59 37.6 Green 55 Comparative Example 103-6 Ref.56: 44.69 35.5 Green 50 Example 712-21-96: 43.85 60.8 Green 170 Example 722-41-596: 43.82 62.0 Green 195 Example 732-151-1016:43.8456.7Green193 Example 742-311-1406:43.8461.2Green166 Example 753-61-2886:43.6460.6Green201 Example 763-271-1106:43.6651.5Green213 Example 773-371-3466:43.6163.0Green208 Example 782-421-4026:43.8162.1Green357 Example 792-471-1436:43.8465.2Green305 Example 802-511-2156:43.8355.2Green313 Example 812-551-4606:43.8259.8Green346 Example 822-681-4666:43.8360.0Green329 Example 833-431-4986:43.6064.3Green358 Example 843-531-466:43.6254.7Green319 Example 853-551-2376:43.6154.4Green304 Example 863-641-2506:43.6555.0Green310 Example 873-711-4716:43.6456.2Green370 Example 883-751-4966:43.6359.2Green375 Example 892-551-6026:43.8556.6Green325 Example 902-531-6456:43.6654.9Green301

[0567]

[0568] When comparing the results of Table 10 above with the results of Table 9 above, it can be seen that when the heterocyclic compound represented by Formula 1 of the present invention and the heterocyclic compound represented by Formula 2 or Formula 3 are simultaneously used as hosts of the light-emitting layer, the driving voltage, luminous efficiency, and lifespan are all improved.

[0569] That is, it was confirmed that excellent device characteristics are exhibited when a heterocyclic compound represented by Chemical Formula 1 is used as the acceptor in the present invention, and a heterocyclic compound represented by Chemical Formula 2 or Chemical Formula 3 is used as the donor in the present invention.

[0570] Accordingly, when the heterocyclic compound represented by Formula 1 of the present invention and the heterocyclic compound represented by Formula 2 or Formula 3 are simultaneously used as hosts of the light-emitting layer, it was confirmed that the driving voltage is low and the luminous efficiency and lifespan are significantly excellent.

[0571]

[0572] [Explanation of the symbol]

[0573] 100: Substrate

[0574] 200: Anode

[0575] 300: Organic layer

[0576] 301: Hole injection layer

[0577] 302: Precision Transport Layer

[0578] 303: Emissive layer

[0579] 304: Main barrier layer

[0580] 305: Electron transport layer

[0581] 306: Electron injection layer

[0582] 400: Cathode

Claims

1. Heterocyclic compounds represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, The above Y is O; or S, and The above R1 to R5 are the same or different from one another and each independently select from the group consisting of hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C2 to C60 alkenyl group; substituted or unsubstituted C2 to C60 alkynyl group; substituted or unsubstituted C1 to C60 alkoxy group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or unsubstituted C2 to C60 heterocycloalkyl group; substituted or unsubstituted C6 to C60 aryl group; substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R101R102; -SiR101R102R103; and -NR101R102, or a C6 to C60 aromatic hydrocarbon ring substituted or unsubstituted by two or more adjacent groups bonded to each other; or forming a substituted or unsubstituted C2 to C60 heterocyclic group, wherein R101, R102, and R103 are the same or different from each other, and each is 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, and The above a1 is an integer from 0 to 4, and if a1 is 2 or greater, R1 are the same or different from each other, and The above a2 is an integer from 0 to 4, and if a2 is 2 or greater, R2 are the same or different from each other, and The above a3 is an integer from 0 to 4, and if a3 is 2 or greater, R3 are the same or different from each other, and The above a4 is an integer from 0 to 3, and if a4 is 2 or greater, R4 are the same or different from each other, and The above a5 is an integer from 0 to 4, and if a5 is 2 or greater, R5 are the same or different from each other, and The above L1 and L2 are the same or different from each other and are each independently directly bonded; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, and The above b1 is an integer from 0 to 5, and if b1 is 2 or greater, L1 are the same or different from each other, and The above b2 is an integer from 0 to 5, and if b2 is 2 or greater, L2 are the same or different from each other, and The above Ar1 and Ar2 are the same or different from each other and are each independently substituted or unsubstituted C6 to C60 aryl groups; or substituted or unsubstituted C2 to C60 heteroaryl groups.

2. In Paragraph 1, A heterocyclic compound represented by the above chemical formula 1, wherein the heterocyclic compound is represented by either the following chemical formula 1-1 or 1-2: [Chemical Formula 1-1] [Chemical Formula 1-2] In the above chemical formulas 1-1 and 1-2, The above a6 is an integer from 0 to 2, and if a6 is 2 or greater, R4 are the same or different from each other, and The above a7 is an integer from 0 to 3, and if a7 is 2 or greater, R5 are the same or different from each other, and The above Y, R1 to R5, L1, L2, Ar1, Ar2, a1 to a5, b1 and b2 are identical to the definitions of Chemical Formula 1.

3. In Paragraph 2, A heterocyclic compound represented by the above chemical formula 1-1, wherein the heterocyclic compound is represented by any one of the following chemical formulas 1-1-1 to 1-1-4: [Chemical Formula 1-1-1] [Chemical Formula 1-1-2] [Chemical Formula 1-1-3] [Chemical Formula 1-1-4] In the above chemical formulas 1-1-1 to 1-1-4, The above Y, R1 to R5, L1, L2, Ar1, Ar2, a1 to a3, a5, b1 and b2 are identical to the definitions of Chemical Formula 1, and The above a6 is identical to the definition of chemical formula 1-1.

4. In Paragraph 2, A heterocyclic compound represented by the above chemical formula 1-2, wherein the heterocyclic compound is represented by any one of the following chemical formulas 1-2-1 to 1-2-4: [Chemical Formula 1-2-1] [Chemical Formula 1-2-2] [Chemical Formula 1-2-3] [Chemical Formula 1-2-4] In the above chemical formulas 1-2-1 to 1-2-4, The above Y, R1 to R5, L1, L2, Ar1, Ar2, a1 to a4, b1 and b2 are identical to the definitions of Chemical Formula 1, and The above a7 is identical to the definition of chemical formula 1-2.

5. In Paragraph 1, A heterocyclic compound wherein R2 and R3 are the same or different from each other and each independently is hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

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

7. In Paragraph 1, A heterocyclic compound represented by the above chemical formula 1, wherein the heterocyclic compound is represented by any one of the following compounds: .

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

9. In Paragraph 8, The above organic layer includes a light-emitting layer, and The above-mentioned light-emitting layer comprises the above-mentioned heterocyclic compound, forming an organic light-emitting device.

10. In Paragraph 8, The above organic layer includes a light-emitting layer, and The above-mentioned light-emitting layer includes a host material, and The above host material is an organic light-emitting device comprising the above heterocyclic compound.

11. In Paragraph 8, An organic light-emitting device wherein the organic layer further comprises a heterocyclic compound represented by the following chemical formula 2 or chemical formula 3: [Chemical Formula 2] [Chemical Formula 3] In the above chemical formulas 2 and 3, The above R11, R12, R21, and R22 are the same or different from each other and each independently hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C2 to C60 alkenyl group; substituted or unsubstituted C2 to C60 alkynyl group; substituted or unsubstituted C1 to C60 alkoxy group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or unsubstituted C2 to C60 heterocycloalkyl group; substituted or unsubstituted C6 to C60 aryl group; substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R201R202; -SiR201R202R203; Selected from the group consisting of -NR201R202, or a C6 to C60 aromatic hydrocarbon ring that is substituted or unsubstituted by combining two or more adjacent groups; or a C2 to C60 heterocyclic ring that is substituted or unsubstituted, wherein R201, R202, and R203 are the same or different from each other and each independently comprises a C1 to C60 alkyl group that is substituted or unsubstituted; a C6 to C60 aryl group that is substituted or unsubstituted; or a C2 to C60 heteroaryl group that is substituted or unsubstituted, and The above c1 is an integer from 0 to 7, and if c1 is 2 or greater, R11 are the same or different from each other, and The above c2 is an integer from 0 to 7, and if c2 is 2 or greater, R12 are the same or different from each other, and The above e1 is an integer from 0 to 6, and if e1 is 2 or greater, R21 are the same or different from each other, and The above e2 is an integer from 0 to 4, and if e2 is 2 or greater, R22 are the same or different from each other, and The above Ar11, Ar12, Ar21, and Ar22 are the same or different from each other and are each independently substituted or unsubstituted C6 to C60 aryl groups; or substituted or unsubstituted C2 to C60 heteroaryl groups, and The above L11, L12, L21, and L22 are the same or different from each other and are each independently directly bonded; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, and The above d1 is an integer from 0 to 5, and if d1 is 2 or greater, L11 are the same or different from each other, and The above d2 is an integer from 0 to 5, and if d2 is 2 or greater, L12 are the same or different from each other, and The above f1 is an integer from 0 to 5, and if f1 is 2 or greater, L21 are the same or different from each other, and The above f2 is an integer from 0 to 5, and if f2 is 2 or more, L22 are the same or different.

12. In Paragraph 11, An organic light-emitting diode (OLED) represented by any one of the following compounds, wherein the heterocyclic compound represented by the above chemical formula 2 is: .

13. In Paragraph 11, An organic light-emitting device, wherein the heterocyclic compound represented by the above chemical formula 3 is represented by any one of the following chemical formulas 3-1 to 3-6: [Chemical Formula 3-1] [Chemical Formula 3-2] [Chemical Formula 3-3] [Chemical Formula 3-4] [Chemical Formula 3-5] [Chemical Formula 3-6] In the above chemical formulas 3-1 to 3-6, The above R21, R22, Ar21, Ar22, L21, L22, e1, e2, f1 and f2 are identical to the definitions of Chemical Formula 3.

14. In Paragraph 11, An organic light-emitting diode (OLED) represented by any one of the following compounds, wherein the heterocyclic compound represented by the above chemical formula 3: .

15. In Paragraph 11, An organic light-emitting device in which a heterocyclic compound represented by the above chemical formula 2 or a heterocyclic compound represented by the above chemical formula 3 does not contain deuterium as a substituent, or the deuterium content relative to the total number of hydrogen atoms and deuterium atoms is 1% to 100%.

16. In Paragraph 8, The organic light-emitting device further comprises one or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

17. A composition for an organic layer comprising a heterocyclic compound represented by Formula 1 of any one of claims 1 to 7 and a heterocyclic compound represented by Formula 2 or Formula 3 below: [Chemical Formula 2] [Chemical Formula 3] In the above chemical formulas 2 and 3, The above R11, R12, R21, and R22 are the same or different from each other and each independently hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C2 to C60 alkenyl group; substituted or unsubstituted C2 to C60 alkynyl group; substituted or unsubstituted C1 to C60 alkoxy group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or unsubstituted C2 to C60 heterocycloalkyl group; substituted or unsubstituted C6 to C60 aryl group; substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)R201R202; -SiR201R202R203; Selected from the group consisting of -NR201R202, or a C6 to C60 aromatic hydrocarbon ring that is substituted or unsubstituted by combining two or more adjacent groups; or a C2 to C60 heterocyclic ring that is substituted or unsubstituted, wherein R201, R202, and R203 are the same or different from each other and each independently comprises a C1 to C60 alkyl group that is substituted or unsubstituted; a C6 to C60 aryl group that is substituted or unsubstituted; or a C2 to C60 heteroaryl group that is substituted or unsubstituted, and The above c1 is an integer from 0 to 7, and if c1 is 2 or greater, R11 are the same or different from each other, and The above c2 is an integer from 0 to 7, and if c2 is 2 or greater, R12 are the same or different from each other, and The above e1 is an integer from 0 to 6, and if e1 is 2 or greater, R21 are the same or different from each other, and The above e2 is an integer from 0 to 4, and if e2 is 2 or greater, R22 are the same or different from each other, and The above Ar11, Ar12, Ar21, and Ar22 are the same or different from each other and are each independently substituted or unsubstituted C6 to C60 aryl groups; or substituted or unsubstituted C2 to C60 heteroaryl groups, and The above L11, L12, L21, and L22 are the same or different from each other and are each independently directly bonded; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, and The above d1 is an integer from 0 to 5, and if d1 is 2 or greater, L11 are the same or different from each other, and The above d2 is an integer from 0 to 5, and if d2 is 2 or greater, L12 are the same or different from each other, and The above f1 is an integer from 0 to 5, and if f1 is 2 or greater, L21 are the same or different from each other, and The above f2 is an integer from 0 to 5, and if f2 is 2 or more, L22 are the same or different.

18. In Paragraph 17, A composition for an organic layer, wherein the weight ratio of a heterocyclic compound represented by the above chemical formula 1 to a heterocyclic compound represented by the above chemical formula 2 or 3 is 1:9 to 9:1.

Images