Organic light-emitting device and composition for organic material layer thereof

Abstract

The present invention relates to an organic light-emitting device and a composition for an organic material layer thereof, wherein the organic material layer comprises: (1) two kinds of heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by chemical formula 1 and chemical formula 2, and one kind of heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by chemical formula 3 and chemical formula 4; or (2) one kind of heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by chemical formula 1 and chemical formula 2, and two kinds of heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by chemical formula 3 and chemical formula 4.

Description

Organic light-emitting diode and composition for the organic layer thereof

[0001] The present application claims the benefit of priority based on Korean Patent Application No. 10-2024-0125699 filed September 13, 2024, Korean Patent Application No. 10-2025-0087629 filed July 1, 2025, and Korean Patent Application No. 10-2025-0129173 filed September 10, 2025, and incorporates all contents disclosed in the documents of said Korean patent applications as part of this specification.

[0002] The present invention relates to an organic light-emitting diode and a composition for the organic layer thereof.

[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 an organic light-emitting device and a composition for the organic layer thereof.

[0014]

[0015] In order to achieve the above objective,

[0016] The present invention

[0017] First electrode;

[0018] A second electrode provided opposite to the first electrode; and

[0019] An organic light-emitting device comprising one or more organic layers provided between the first electrode and the second electrode,

[0020] At least one layer among the above organic layers is

[0021] (1) Two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by the following chemical formulas 1 and 2; and one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by the following chemical formulas 3 and 4, or

[0022] (2) An organic light-emitting device comprising: one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by the following chemical formulas 1 and 2; and two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by the following chemical formulas 3 and 4.

[0023] [Chemical Formula 1]

[0024]

[0025] [Chemical Formula 2]

[0026]

[0027] [Chemical Formula 3]

[0028]

[0029] [Chemical Formula 4]

[0030]

[0031] In the above chemical formulas 1 to 4,

[0032] The above R1 to R3, R11 to R15, R21, R22, R31 and R32 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)R101R102; -SiR101R102R103; Selected from the group consisting of -NR101R102, or a C6 to C60 aromatic hydrocarbon ring that is substituted or unsubstituted by combining two or more adjacent groups; or forming a substituted or unsubstituted C2 to C60 heterocyclic ring, wherein R101, R102, and R103 are the same or different from each other and each independently comprises a 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

[0033] The above a1 to a3, c1 to c5 and e2 are the same or different from each other, and each is independently an integer from 0 to 4, and

[0034] The above e1 is an integer from 0 to 6, and

[0035] The above g1 and g2 are the same or different from each other, and each is independently an integer from 0 to 7, and

[0036] The above Ar1, Ar2, Ar11, Ar21, Ar22, Ar31, and Ar32 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

[0037] The above L1, L2, L12, L21, L22, L31 and L32 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

[0038] The above L11 is a substituted or unsubstituted C6 to C60 arylene group, and

[0039] The above b1, b2, d1, d2, f1, f2, h1, and h2 are the same or different from each other, and each is independently an integer from 0 to 5, and

[0040] If Ar1 is a substituted or unsubstituted carbazolyl group, L1 is a direct bond; or a substituted or unsubstituted C2 to C60 heteroarylene group, and if Ar2 is a substituted or unsubstituted carbazolyl group, L2 is a direct bond; or a substituted or unsubstituted C2 to C60 heteroarylene group.

[0041]

[0042] In addition, the present invention provides a composition for an organic layer comprising two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Formula 1 and Formula 2; and one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Formula 3 and Formula 4.

[0043] In addition, the present invention provides a composition for an organic layer comprising: one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Formula 1 and Formula 2; and two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Formula 3 and Formula 4.

[0044]

[0045] The organic light-emitting device of the present invention is, as a material of the organic layer,

[0046] (1) Two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2; and one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 3 and Chemical Formula 4, or

[0047] (2) By including one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by the above chemical formulas 1 and 2; and two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by the above chemical formulas 3 and 4, the driving voltage of the organic light-emitting device can be lowered and the luminous efficiency and lifespan characteristics can be improved.

[0048]

[0049] FIGS. 1 to 3 are schematic diagrams illustrating the stacked structure of an organic light-emitting device according to an embodiment of the present invention.

[0050]

[0051] The present invention will be described in more detail below.

[0052]

[0053] 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.

[0054] 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.

[0055] In this specification, the halogen may be fluorine; chlorine; bromine; or iodine.

[0056] 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.

[0057] 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.

[0058] 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.

[0059] 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.

[0060] 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.

[0061] 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.

[0062] 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.

[0063] 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.

[0064] 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.

[0065] In the present specification, the fluorenyl group may be substituted, and adjacent substituents may combine with each other to form a ring.

[0066] When the above fluorenyl group is substituted, It may include, but is not limited to, etc.

[0067] 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.

[0068]

[0069] 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; quinozoliryl 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.

[0070] 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.

[0071] 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.

[0072] 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.

[0073] 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.

[0074] 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%.

[0075] 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.

[0076] 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.

[0077] 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.

[0078] 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.

[0079] 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.

[0080]

[0081]

[0082] 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.

[0083] 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.

[0084]

[0085] The present invention relates to an organic light-emitting device, and the organic light-emitting device of the present invention is

[0086] First electrode;

[0087] A second electrode provided opposite to the first electrode; and

[0088] It includes one or more organic layers provided between the first electrode and the second electrode; and

[0089] At least one layer among the above organic layers is

[0090] (1) Two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by the following chemical formulas 1 and 2; and one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by the following chemical formulas 3 and 4, or

[0091] (2) It may include one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by the following chemical formulas 1 and 2; and two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by the following chemical formulas 3 and 4.

[0092] [Chemical Formula 1]

[0093]

[0094] [Chemical Formula 2]

[0095]

[0096] [Chemical Formula 3]

[0097]

[0098] [Chemical Formula 4]

[0099]

[0100] In the above chemical formulas 1 to 4,

[0101] The above R1 to R3, R11 to R15, R21, R22, R31 and R32 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)R101R102; -SiR101R102R103; Selected from the group consisting of -NR101R102, or a C6 to C60 aromatic hydrocarbon ring that is substituted or unsubstituted by combining two or more adjacent groups; or forming a substituted or unsubstituted C2 to C60 heterocyclic ring, wherein R101, R102, and R103 are the same or different from each other and each independently comprises a 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 to a3, c1 to c5 and e2 are the same or different from each other, and each is independently an integer from 0 to 4, and

[0103] The above e1 is an integer from 0 to 6, and

[0104] The above g1 and g2 are the same or different from each other, and each is independently an integer from 0 to 7, and

[0105] The above Ar1, Ar2, Ar11, Ar21, Ar22, Ar31, and Ar32 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

[0106] The above L1, L2, L12, L21, L22, L31 and L32 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

[0107] The above L11 is a substituted or unsubstituted C6 to C60 arylene group, and

[0108] The above b1, b2, d1, d2, f1, f2, h1, and h2 are the same or different from each other, and each is independently an integer from 0 to 5, and

[0109] If Ar1 is a substituted or unsubstituted carbazolyl group, L1 is a direct bond; or a substituted or unsubstituted C2 to C60 heteroarylene group, and if Ar2 is a substituted or unsubstituted carbazolyl group, L2 is a direct bond; or a substituted or unsubstituted C2 to C60 heteroarylene group.

[0110]

[0111] In one embodiment of the present invention, R1 to R3, R11 to R15, R21, R22, R31 and R32 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)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.

[0112] In another embodiment of the present invention, R1 to R3, R11 to R15, R21, R22, R31 and R32 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)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.

[0113] In another embodiment of the present invention, R1 to R3, R11 to R15, R21, R22, R31 and R32 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 C6 to C20 aryl group; or substituted or unsubstituted C2 to C20 heteroaryl group.

[0114] In another embodiment of the present invention, R1 to R3, R11 to R15, R21, R22, R31 and R32 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.

[0115] In another embodiment of the present invention, R1 and R11 may be the same or different from each other and may each independently be hydrogen; deuterium; or a substituted or unsubstituted C6 to C60 aryl group.

[0116] In another embodiment of the present invention, R1 and R11 may be the same or different from each other and may each independently be hydrogen; deuterium; or a substituted or unsubstituted C6 to C30 aryl group.

[0117] In another embodiment of the present invention, R1 and R11 may be the same or different from each other and may each independently be hydrogen; deuterium; or a substituted or unsubstituted C6 to C20 aryl group.

[0118] In another embodiment of the present invention, R1 and R11 may be the same or different from each other and may each independently be hydrogen; deuterium; or a substituted or unsubstituted phenyl group.

[0119] In another embodiment of the present invention, R21 and R22 may be the same or different from each other and may each independently be hydrogen; or deuterium.

[0120] In another embodiment of the present invention, R31 and R32 may be the same or different from each other and may each independently be hydrogen; or deuterium.

[0121] In another embodiment of the present invention, R2, R3 and R12 to R15 may be the same or different from each other and may each independently be hydrogen; deuterium; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0122] In another embodiment of the present invention, R2, R3 and R12 to R15 may be the same or different from each other and may each independently be hydrogen; deuterium; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0123] In another embodiment of the present invention, R2, R3 and R12 to R15 may be the same or different from each other and may each independently be hydrogen; deuterium; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0124] In another embodiment of the present invention, R2, R3 and R12 to R15 may be the same or different from each other and may each independently be hydrogen; deuterium; or a substituted or unsubstituted C6 to C20 aryl group.

[0125] In another embodiment of the present invention, R2, R3 and R12 to R15 may be the same or different from each other and may each independently be hydrogen; deuterium; a substituted or unsubstituted phenyl group; or a substituted or unsubstituted biphenyl 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 phenyl group; or a substituted or unsubstituted biphenyl group.

[0127] In another embodiment of the present invention, R12 to R15 may be the same or different from one another and may each independently be hydrogen; deuterium; or a substituted or unsubstituted phenyl group.

[0128]

[0129] In one embodiment of the present invention, Ar1, Ar2, Ar11, Ar21, Ar22, Ar31, and Ar32 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, Ar2, Ar11, Ar21, Ar22, Ar31, and Ar32 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, Ar2, Ar11, Ar21, Ar22, Ar31 and Ar32 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 fluoranthenyl 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, 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.

[0133] 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 fluoranthenyl 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.

[0134] 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.

[0135] 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.

[0136] In another embodiment of the present invention, Ar31 and Ar32 may be 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 dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group.

[0137]

[0138] In one embodiment of the present invention, L1, L2, L12, L21, L22, L31, and L32 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.

[0139] In another embodiment of the present invention, L1, L2, L12, L21, L22, L31 and L32 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.

[0140] In another embodiment of the present invention, L1, L2, L12, L21, L22, L31 and L32 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; a substituted or unsubstituted dibenzofuranylene group; a substituted or unsubstituted dibenzothiophenylene group; or a substituted or unsubstituted carbazolene group.

[0141] 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 carbazolene group.

[0142] In another embodiment of the present invention, the L12 may be a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted dibenzofuranilene group; or a substituted or unsubstituted dibenzothiophenylene group.

[0143] 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.

[0144] 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.

[0145] In another embodiment of the present invention, L31 and L32 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.

[0146]

[0147] In one embodiment of the present invention, L11 may be a substituted or unsubstituted C6 to C30 arylene group.

[0148] In another embodiment of the present invention, L11 may be a substituted or unsubstituted C6 to C20 arylene group.

[0149] In another embodiment of the present invention, L11 may be a substituted or unsubstituted phenylene group; or a substituted or unsubstituted biphenylene group.

[0150]

[0151] In one embodiment of the present invention, R1 to R3, L1, L2, Ar1 and Ar2 may all include undeuterated hydrogen (H).

[0152] In another embodiment of the present invention, at least one of R1 to R3, L1, L2, Ar1 and Ar2 comprises deuterium (D), and at least one of R1 to R3, L1, L2, Ar1 and Ar2 may comprise undeuterinized hydrogen.

[0153] In another embodiment of the present invention, R1 to R3, L1, L2, Ar1 and Ar2 may all include deuterium.

[0154]

[0155] 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%.

[0156] 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%.

[0157] 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%.

[0158] 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%.

[0159] 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%.

[0160]

[0161] 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.

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183] In one embodiment of the present invention, R11 to R15, L11, L12 and Ar11 may all include undeuterated hydrogen (H).

[0184] In another embodiment of the present invention, at least one of R11 to R15, L11, L12 and Ar11 comprises deuterium (D), and at least one of R11 to R15, L11, L12 and Ar11 may comprise undeuterinized hydrogen.

[0185] In another embodiment of the present invention, R11 to R15, L11, L12, and Ar11 may all include deuterium.

[0186]

[0187] 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%.

[0188] 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%.

[0189] 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%.

[0190] 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%.

[0191] 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%.

[0192]

[0193] 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.

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212] 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.

[0213] [Chemical Formula 3-1]

[0214]

[0215] [Chemical Formula 3-2]

[0216]

[0217] [Chemical Formula 3-3]

[0218]

[0219] [Chemical Formula 3-4]

[0220]

[0221] [Chemical Formula 3-5]

[0222]

[0223] [Chemical Formula 3-6]

[0224]

[0225] In the above chemical formulas 3-1 to 3-6,

[0226] The above R21, R22, Ar21, Ar22, L21, L22, e1, e2, f1 and f2 are identical to the definitions of Chemical Formula 3.

[0227]

[0228] In one embodiment of the present invention, R21, R22, L21, L22, Ar21 and Ar22 may all include undeuterated hydrogen (H).

[0229] In another embodiment of the present invention, at least one of R21, R22, L21, L22, Ar21 and Ar22 comprises deuterium (D), and at least one of R21, R22, L21, L22, Ar21 and Ar22 may comprise undeuterinized hydrogen.

[0230] In another embodiment of the present invention, R21, R22, L21, L22, Ar21, and Ar22 may all include deuterium.

[0231]

[0232] 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%.

[0233] 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%.

[0234] 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%.

[0235] 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%.

[0236] 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%.

[0237]

[0238] 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.

[0239]

[0240]

[0241]

[0242]

[0243]

[0244] In one embodiment of the present invention, R31, R32, L31, L32, Ar31 and Ar32 may all include undeuterated hydrogen (H).

[0245] In another embodiment of the present invention, at least one of R31, R32, L31, L32, Ar31 and Ar32 comprises deuterium (D), and at least one of R31, R32, L31, L32, Ar31 and Ar32 may comprise undeuterinized hydrogen.

[0246] In another embodiment of the present invention, R31, R32, L31, L32, Ar31, and Ar32 may all contain deuterium.

[0247]

[0248] In one embodiment of the present invention, the heterocyclic compound represented by Formula 4 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%.

[0249] In another embodiment of the present invention, the heterocyclic compound represented by Formula 4 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%.

[0250] In another embodiment of the present invention, the heterocyclic compound represented by Formula 4 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%.

[0251] In another embodiment of the present invention, the heterocyclic compound represented by the chemical formula 4 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%.

[0252] In another embodiment of the present invention, the heterocyclic compound represented by Formula 4 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%.

[0253]

[0254] In one embodiment of the present invention, the heterocyclic compound represented by the chemical formula 4 may be represented by any one of the following compounds.

[0255]

[0256]

[0257]

[0258]

[0259]

[0260] The above 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."

[0261]

[0262] In one embodiment of the present invention, the first electrode may be an anode, and the second electrode may be a cathode.

[0263] In another embodiment of the present invention, the first electrode may be a negative electrode, and the second electrode may be a positive electrode.

[0264]

[0265] In one embodiment of the present invention, the organic light-emitting element may be a red organic light-emitting element, and two types of heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2; and one type of heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 3 and Chemical Formula 4 may be used as a material for the red organic light-emitting element.

[0266] In another embodiment of the present invention, the organic light-emitting element may be a blue organic light-emitting element, and two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2; and one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 3 and Chemical Formula 4 may be used as a material for the blue organic light-emitting element.

[0267] In another embodiment of the present invention, the organic light-emitting element may be a green organic light-emitting element, and two types of heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2; and one type of heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 3 and Chemical Formula 4 may be used as a material for the green organic light-emitting element.

[0268] In another embodiment of the present invention, the organic light-emitting element may be a red organic light-emitting element, and one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2; and two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formula 3 and Chemical Formula 4 may be used as materials for the red organic light-emitting element.

[0269] In another embodiment of the present invention, the organic light-emitting element may be a blue organic light-emitting element, and one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2; and two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formula 3 and Chemical Formula 4 may be used as materials for a blue organic light-emitting material.

[0270] In another embodiment of the present invention, the organic light-emitting element may be a green organic light-emitting element, and one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2; and two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formula 3 and Chemical Formula 4 may be used as materials for the green organic light-emitting material.

[0271]

[0272] In one embodiment of the present invention, the organic light-emitting element may be a red organic light-emitting element, and two types of heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2; and one type of heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 3 and Chemical Formula 4 may be used as a light-emitting layer material of the red organic light-emitting element.

[0273] In another embodiment of the present invention, the organic light-emitting element may be a blue organic light-emitting element, and two types of heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2; and one type of heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 3 and Chemical Formula 4 may be used as a light-emitting layer material of the blue organic light-emitting element.

[0274] In another embodiment of the present invention, the organic light-emitting device may be a green organic light-emitting device, and two types of heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2; and one type of heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 3 and Chemical Formula 4 may be used as a light-emitting layer material of the green organic light-emitting device.

[0275] In another embodiment of the present invention, the organic light-emitting element may be a red organic light-emitting element, and one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2; and two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formula 3 and Chemical Formula 4 may be used as a light-emitting layer material of the red organic light-emitting element.

[0276] In another embodiment of the present invention, the organic light-emitting element may be a blue organic light-emitting element, and one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2; and two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formula 3 and Chemical Formula 4 may be used as a light-emitting layer material of the blue organic light-emitting element.

[0277] In another embodiment of the present invention, the organic light-emitting device may be a green organic light-emitting device, and one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2; and two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formula 3 and Chemical Formula 4 may be used as a light-emitting layer material of the green organic light-emitting device.

[0278]

[0279] The organic light-emitting device of the present invention can be manufactured by a conventional method and material for manufacturing an organic light-emitting device, except that one or more organic layers are formed using the aforementioned (1) two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2; and one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 3 and Chemical Formula 4, or (2) one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2; and two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formula 3 and Chemical Formula 4.

[0280] (1) two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2; and one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 3 and Chemical Formula 4, or (2) two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2; and one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 3 and Chemical Formula 4 can be formed as an organic layer by vacuum deposition as well as by solution coating. Here, solution coating refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.

[0281] 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.

[0282]

[0283] In the organic light-emitting device of the present invention, the organic layer comprises (1) two types of heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2; With respect to the total weight of the sum of the heterocyclic compounds represented by Chemical Formula 3 and Chemical Formula 4 and one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 3 and Chemical Formula 4, the one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 3 and Chemical Formula 4 may be included in an amount of 10 wt% or more, 20 wt% or more, 30 wt% or more, 40 wt% or more, 45 wt% or more, 50 wt% or more, 55 wt% or more, 60 wt% or more, 65 wt% or more, 70 wt% or more, 75 wt% or more, or 80 wt% or more, and may be included in an amount of 90 wt% or less, 85 wt% or less, 80 wt% or less, 75 wt% or less, 70 wt% or less, 65 wt% or less, 60 wt% or less, or 50 wt% or less. One heterocyclic compound selected from the group consisting of heterocyclic compounds represented by the above chemical formulas 3 and 4 may be included in an amount of 10 to 90 weight%, preferably 20 to 80 weight%, more preferably 40 to 60 weight%, and most preferably 50 to 70 weight%.

[0284] In the organic light-emitting device of the present invention, the organic layer comprises (2) one type of heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2; With respect to the total weight of the two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formula 3 and Chemical Formula 4, the two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formula 3 and Chemical Formula 4 may be included in an amount of 10 wt% or more, 20 wt% or more, 30 wt% or more, 40 wt% or more, 45 wt% or more, 50 wt% or more, 55 wt% or more, 60 wt% or more, 65 wt% or more, 70 wt% or more, 75 wt% or more, or 80 wt% or more, and may be included in an amount of 90 wt% or less, 85 wt% or less, 80 wt% or less, 75 wt% or less, 70 wt% or less, 65 wt% or less, 60 wt% or less, or 50 wt% or less. Two types of heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by the above chemical formulas 3 and 4 may be included in an amount of 10 to 90 weight%, preferably 20 to 80 weight%, more preferably 40 to 60 weight%, and most preferably 50 to 70 weight%.

[0285]

[0286] The organic layer of the organic light-emitting device of the present invention may exhibit superior efficiency and lifespan effects by comprising (1) two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2; and one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 3 and Chemical Formula 4, or (2) one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2; and two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formula 3 and Chemical Formula 4. From this, (1) two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2; and one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formulas 3 and 4, or (2) one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formulas 1 and 2; and two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formulas 3 and 4 together, it can be expected that an exciplex phenomenon will occur. In addition, it may include one heterocyclic compound represented by Chemical Formula 1; one heterocyclic compound represented by Chemical Formula 2; and one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formulas 3 and 4, or one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formulas 1 and 2; and one heterocyclic compound represented by Chemical Formula 3; It is preferable to include one type of heterocyclic compound represented by the above chemical formula 4.In this case, the irregularity of the molecular arrangement within the emissive layer increases, which can induce light scattering and isotropic luminescence, thereby enabling the production of an organic light-emitting device with excellent viewing angle and brightness.

[0287] 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. The organic light-emitting device of the present invention uses a heterocyclic compound represented by Formula 1 or a heterocyclic compound represented by Formula 2 as the acceptor (n-host) and a heterocyclic compound represented by Formula 3 or a heterocyclic compound represented by Formula 4 as the donor (p-host), so that it can exhibit excellent device characteristics.

[0288] Specifically, the organic layer of the organic light-emitting device of the present invention may include two types of n-hosts and one type of p-host, or one type of n-host and two types of p-hosts.

[0289] In one embodiment of the present invention, the two types of n-hosts are two types of heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2, and the one type of p-host may be one type of heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 3 and Chemical Formula 4.

[0290] In another embodiment of the present invention, the two types of n-hosts are two types of heterocyclic compounds represented by Formula 1, and the one type of p-host may be one type of heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Formulas 3 and 4.

[0291] In another embodiment of the present invention, the two types of n-hosts are two types of heterocyclic compounds represented by Formula 2, and the one type of p-host may be one type of heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Formulas 3 and 4.

[0292] In another embodiment of the present invention, the two types of n-hosts are one type of heterocyclic compound represented by Formula 1 and one type of heterocyclic compound represented by Formula 2, and the one type of p-host may be one type of heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Formulas 3 and 4.

[0293] In another embodiment of the present invention, the one type of n-host may be a heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2, and the two types of p-host may be two types of heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formula 3 and Chemical Formula 4.

[0294] In another embodiment of the present invention, the one type of n-host is a heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2, and the two types of p-hosts may be two types of heterocyclic compounds represented by Chemical Formula 3.

[0295] In another embodiment of the present invention, the one type of n-host is a heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2, and the two types of p-hosts may be two types of heterocyclic compounds represented by Chemical Formula 4.

[0296] In another embodiment of the present invention, the one n-host is a heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2, and the two p-hosts may be a heterocyclic compound represented by Chemical Formula 3 and a heterocyclic compound represented by Chemical Formula 4.

[0297] Accordingly, the organic layer of an organic light-emitting device according to one embodiment of the present invention may preferably contain 50% by weight or more of p-host based on the total weight of (1) two types of heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Formula 1 and Formula 2; and one type of heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Formula 3 and Formula 4.

[0298] Accordingly, the organic layer of an organic light-emitting device according to another embodiment of the present invention may preferably contain 50% by weight or more of p-host based on the total weight of the sum of (2) one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Formula 1 and Formula 2; and two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Formula 3 and Formula 4.

[0299] Generally, the speed of holes is slower than the speed of electrons. If p-host is included in an amount of 50 wt% or more to balance holes and electrons, the balance between holes and electrons is appropriate, allowing many excitons to be formed within the light-emitting layer, thereby obtaining an organic light-emitting device with excellent characteristics.

[0300]

[0301] 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 (1) two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2; and one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 3 and Chemical Formula 4, or (2) one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2; and two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formula 3 and Chemical Formula 4. When the heterocyclic compounds are 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 HOMO (Highest Occupied Molecular Orbital) and LUMO (Lowest Unoccupied Molecular Orbital).

[0302]

[0303] In an organic light-emitting device according to one embodiment of the present invention, the organic layer comprises a light-emitting layer, and the light-emitting layer may comprise two types of heterocyclic compounds represented by Formula 1; and one type of heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Formulas 3 and 4.

[0304] In an organic light-emitting device according to another embodiment of the present invention, the organic layer comprises a light-emitting layer, and the light-emitting layer may comprise two types of heterocyclic compounds represented by Formula 2; and one type of heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Formulas 3 and 4.

[0305] In an organic light-emitting device according to another embodiment of the present invention, the organic layer comprises a light-emitting layer, and the light-emitting layer may comprise a heterocyclic compound selected from the group consisting of a heterocyclic compound represented by Formula 1; a heterocyclic compound represented by Formula 2; and a heterocyclic compound represented by Formulas 3 and 4.

[0306] In an organic light-emitting device according to another embodiment of the present invention, the organic layer comprises a light-emitting layer, and the light-emitting layer may comprise one heterocyclic compound selected from the group represented by Chemical Formula 1 and Chemical Formula 2; and two heterocyclic compounds represented by Chemical Formula 3.

[0307] In an organic light-emitting device according to another embodiment of the present invention, the organic layer comprises a light-emitting layer, and the light-emitting layer may comprise one heterocyclic compound selected from the group represented by Chemical Formula 1 and Chemical Formula 2; and two heterocyclic compounds represented by Chemical Formula 4.

[0308] In an organic light-emitting device according to another embodiment of the present invention, the organic layer comprises a light-emitting layer, and the light-emitting layer may comprise one heterocyclic compound selected from the group represented by Chemical Formula 1 and Chemical Formula 2; one heterocyclic compound represented by Chemical Formula 3; and one heterocyclic compound represented by Chemical Formula 4.

[0309]

[0310] In the organic light-emitting device of the present invention, the organic layer comprises a light-emitting layer and a light-emitting layer host material, and the host material may comprise (1) two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2; and one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 3 and Chemical Formula 4, or (2) one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2; and two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formula 3 and Chemical Formula 4.

[0311]

[0312] In an organic light-emitting device according to one embodiment of the present invention, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises a host material, wherein the host material may comprise two types of heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2; and one type of heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 3 and Chemical Formula 4.

[0313] In an organic light-emitting device according to another embodiment of the present invention, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises a host material, wherein the host material may comprise two types of heterocyclic compounds represented by Formula 1; and one type of heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Formulas 3 and 4.

[0314] In an organic light-emitting device according to another embodiment of the present invention, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises a host material, wherein the host material may comprise two types of heterocyclic compounds represented by Chemical Formula 2; and one type of heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formulas 3 and 4.

[0315] In an organic light-emitting device according to another embodiment of the present invention, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises a host material, wherein the host material may comprise a heterocyclic compound selected from the group consisting of a heterocyclic compound represented by Formula 1; a heterocyclic compound represented by Formula 2; and a heterocyclic compound represented by Formulas 3 and 4.

[0316] In an organic light-emitting device according to another embodiment of the present invention, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises a host material, wherein the host material may comprise one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2; and two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formula 3 and Chemical Formula 4.

[0317] In an organic light-emitting device according to another embodiment of the present invention, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises a host material, wherein the host material may comprise one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2; and two heterocyclic compounds represented by Chemical Formula 3.

[0318] In an organic light-emitting device according to another embodiment of the present invention, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises a host material, wherein the host material may comprise one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2; and two heterocyclic compounds represented by Chemical Formula 4.

[0319] In an organic light-emitting device according to another embodiment of the present invention, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises a host material, wherein the host material may comprise one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2; one heterocyclic compound represented by Chemical Formula 3; and one heterocyclic compound represented by Chemical Formula 4.

[0320]

[0321] In one embodiment of the present invention, the organic layer comprises two types of heterocyclic compounds represented by Formula 1; and one type of heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Formulas 3 and 4, and can be used together with a phosphorescent dopant.

[0322] In another embodiment of the present invention, the organic layer comprises two types of heterocyclic compounds represented by Formula 2; and one type of heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Formulas 3 and 4, and can be used together with a phosphorescent dopant.

[0323] In another embodiment of the present invention, the organic layer comprises one heterocyclic compound represented by Formula 1; one heterocyclic compound represented by Formula 2; and one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Formulas 3 and 4, and can be used together with a phosphorescent dopant.

[0324] In another embodiment of the present invention, the organic layer comprises one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Formula 1 and Formula 2; and two heterocyclic compounds represented by Formula 3, and can be used together with a phosphorescent dopant.

[0325] In another embodiment of the present invention, the organic layer comprises one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Formula 1 and Formula 2; and two heterocyclic compounds represented by Formula 4, and can be used together with a phosphorescent dopant.

[0326] In another embodiment of the present invention, the organic layer comprises one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Formula 1 and Formula 2; one heterocyclic compound represented by Formula 3; and one heterocyclic compound represented by Formula 4, and can be used together with a phosphorescent dopant.

[0327]

[0328] 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.

[0329] The above M can be iridium, platinum, osmium, etc.

[0330] The above L is sp 2 X 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.

[0331] Specific examples of the above-mentioned phosphorescent dopants are shown below, but are not limited to these examples.

[0332]

[0333]

[0334] In one embodiment of the present invention, the organic layer comprises two types of heterocyclic compounds represented by Formula 1; and one type of heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Formulas 3 and 4, and can be used together with an iridium-based dopant.

[0335] In another embodiment of the present invention, the organic layer comprises two types of heterocyclic compounds represented by Formula 2; and one type of heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Formulas 3 and 4, and can be used together with an iridium-based dopant.

[0336] In another embodiment of the present invention, the organic layer comprises one heterocyclic compound represented by Formula 1; one heterocyclic compound represented by Formula 2; and one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Formulas 3 and 4, and can be used together with an iridium-based dopant.

[0337] In another embodiment of the present invention, the organic layer comprises one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Formula 1 and Formula 2; and two heterocyclic compounds represented by Formula 3, and can be used together with an iridium-based dopant.

[0338] In another embodiment of the present invention, the organic layer comprises one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Formula 1 and Formula 2; and two heterocyclic compounds represented by Formula 4, and can be used together with an iridium-based dopant.

[0339] In another embodiment of the present invention, the organic layer comprises one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Formula 1 and Formula 2; one heterocyclic compound represented by Formula 3; and one heterocyclic compound represented by Formula 4, and can be used together with an iridium-based dopant.

[0340]

[0341] 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.

[0342]

[0343] 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.

[0344]

[0345] Two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2; one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 3 and Chemical Formula 4, or one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2; and two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formula 3 and Chemical Formula 4 may be used after pre-mixing.

[0346] The above pre-mixed means mixing two types of heterocyclic compounds represented by Chemical Formula 1; and one type of heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formulas 3 and 4, and mixing them in a single source before depositing them as a light-emitting layer.

[0347] The above pre-mixed means mixing two types of heterocyclic compounds represented by Chemical Formula 2; and one type of heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formulas 3 and 4, and mixing them in a single source before depositing them as a light-emitting layer.

[0348] The above pre-mixed means mixing one heterocyclic compound selected from the group consisting of one heterocyclic compound represented by Chemical Formula 1; one heterocyclic compound represented by Chemical Formula 2; and heterocyclic compounds represented by Chemical Formulas 3 and 4, by first mixing them in a single source before depositing them as a light-emitting layer.

[0349] The above pre-mixed means mixing one type of heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2; and two types of heterocyclic compounds represented by Chemical Formula 3, by first mixing them in a single source before depositing them as a light-emitting layer.

[0350] The above pre-mixed means mixing one type of heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2; and two types of heterocyclic compounds represented by Chemical Formula 4, by first mixing them in a single source before depositing them as a light-emitting layer.

[0351] The above pre-mixed means mixing one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2; one heterocyclic compound represented by Chemical Formula 3; and one heterocyclic compound represented by Chemical Formula 4 by first mixing them in a single source before depositing them as a light-emitting layer.

[0352]

[0353] 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.

[0354]

[0355] 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.

[0356] 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.

[0357] 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.

[0358]

[0359] In addition, the present invention relates to a composition for an organic layer comprising two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2; and one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 3 and Chemical Formula 4, wherein the composition for an organic layer may be a composition for an organic layer of an organic light-emitting device.

[0360] The specific details regarding the heterocyclic compound represented by Chemical Formula 1, the heterocyclic compound represented by Chemical Formula 2, the heterocyclic compound represented by Chemical Formula 3, and the heterocyclic compound represented by Chemical Formula 4 are the same as those described above.

[0361] In one embodiment of the present invention, the weight ratio of two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Formula 1 and Formula 2 in the composition for the organic layer; and one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Formula 3 and Formula 4 may be 1:9 to 9:1, preferably 2:8 to 8:2, more preferably 1:4 to 1:1, and most preferably 2:3 to 1:1, but is not limited thereto.

[0362] In another embodiment of the present invention, the weight ratio of two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Formula 1 and Formula 2 in the composition for the organic layer may be 1:9 to 9:1, preferably 2:8 to 8:2, and more preferably 1:1, but is not limited thereto.

[0363]

[0364] In addition, the present invention relates to a composition for an organic layer comprising: one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2; and two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formula 3 and Chemical Formula 4, wherein the composition for an organic layer may be a composition for an organic layer of an organic light-emitting device.

[0365] The specific details regarding the heterocyclic compound represented by Chemical Formula 1, the heterocyclic compound represented by Chemical Formula 2, the heterocyclic compound represented by Chemical Formula 3, and the heterocyclic compound represented by Chemical Formula 4 are the same as those described above.

[0366] In one embodiment of the present invention, the weight ratio of one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Formula 1 and Formula 2 in the composition for the organic layer; and two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Formula 3 and Formula 4 may be 1:9 to 9:1, preferably 2:8 to 8:2, more preferably 1:4 to 1:1, and most preferably 2:3 to 1:1, but is not limited thereto.

[0367] In another embodiment of the present invention, the weight ratio of two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Formula 3 and Formula 4 in the composition for the organic layer may be 1:9 to 9:1, preferably 2:8 to 8:2, and more preferably 1:1, but is not limited thereto.

[0368]

[0369] 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.

[0370]

[0371] In one embodiment of the present invention,

[0372] Step of preparing the substrate;

[0373] A step of forming a first electrode on the substrate;

[0374] A step of forming one or more organic layers on the first electrode; and

[0375] 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 the composition for organic layers of the present invention.

[0376]

[0377] In one embodiment of the present invention, the step of forming the organic layer may be to pre-mix two types of heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Formula 1 and Formula 2; and one type of heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Formula 3 and Formula 4, and to form the layer using a thermal vacuum deposition method.

[0378] In another embodiment of the present invention, the step of forming the organic layer may be to pre-mix one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Formula 1 and Formula 2; and two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Formula 3 and Formula 4, and to form the layer using a thermal vacuum deposition method.

[0379] The pre-mixed material may be referred to as a composition for an organic layer according to one embodiment of the present application.

[0380] An organic layer comprising two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2; and one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 3 and Chemical Formula 4 may additionally include other materials as needed.

[0381] An organic layer comprising one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2; and two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formula 3 and Chemical Formula 4 may additionally include other materials as needed.

[0382]

[0383] 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, the heterocyclic compound represented by Formula 3, and the heterocyclic compound represented by Formula 4 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.

[0384]

[0385] 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.

[0386]

[0387] 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.

[0388]

[0389] 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.

[0390]

[0391] 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.

[0392]

[0393] 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.

[0394]

[0395] For example, LiF is commonly used in the industry as an electron injection layer material, but the present application is not limited thereto.

[0396]

[0397] 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.

[0398]

[0399] 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.

[0400]

[0401] 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.

[0402]

[0403] A heterocyclic compound according to one embodiment of the present invention can also function 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.

[0404]

[0405] 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.

[0406]

[0407] <Preparation Example>

[0408] Preparation Example 1. Preparation of Compound 1-9

[0409]

[0410]

[0411] Preparation Example 1-1. Preparation of Compound P-3

[0412] 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 100℃ for 6 hours.

[0413] 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.

[0414]

[0415] Preparation Example 1-2. Preparation of Compound P-2

[0416] 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 100℃ for 5 hours.

[0417] 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.

[0418]

[0419] Preparation Example 1-3. Preparation of Compound P-1

[0420] 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 100℃ for 6 hours.

[0421] 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.

[0422]

[0423] Preparation Example 1-4. Preparation of Compound 1-9

[0424] 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.

[0425] 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.

[0426]

[0427] The target compounds of Table 1 below were synthesized by the same method as in Preparation Example 1 below, 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.

[0428]

[0429]

[0430]

[0431]

[0432]

[0433]

[0434]

[0435]

[0436]

[0437]

[0438]

[0439]

[0440]

[0441]

[0442]

[0443]

[0444]

[0445]

[0446] Preparation Example 2. Preparation of Compound 1-122

[0447]

[0448]

[0449] Preparation Example 2-1. Preparation of Compound S-2

[0450] 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 100°F for 6 hours.

[0451] 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 77%) of compound S-2, a white solid.

[0452]

[0453] Preparation Example 2-2. Preparation of Compound S-1

[0454] Compounds S-2 (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 100℃ for 5 hours.

[0455] 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-1, a white solid.

[0456]

[0457] Preparation Example 2-3. Preparation of Compound 1-122

[0458] Compound S-1 (19.5g, 42.45mmol), 9-(2-(4-([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazin-2-yl)phenyl)-9H-carbazole (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 100℃ for 6 hours.

[0459] 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 1-122, a yellow solid.

[0460]

[0461] The target compounds of Table 2 below were synthesized by the same method as in Preparation Example 2 above, except that in Preparation Example 2 below, compound E of Table 2 below was used instead of 2-bromo-7-chlorodibenzo[b,d]furan, compound F of Table 2 below was used instead of 9H-carbazole, and compound G of Table 2 below was used instead of 9-(2-(4-([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine-2-yl)phenyl)-9H-carbazole.

[0462]

[0463]

[0464]

[0465]

[0466]

[0467] Compound number 1H NMR(CDCl3, 300MHz)1-98.55(1H, s), 8.28(2H, d), 8.12(1H, d), 7.95(1H, d), 7.94(1H, d), 7.79(1H, d), 7.75(2H, d), 7.68(1H, d), 7.64(1H, d), 7.63(1H, dd), 7.62(1H, d), 7.54(1H, d), 7.52(2H, dd), 7.51(5H, dd), 7.5(1H, s), 7.44 (1H, t), 7.41 (2H, t), 7.33 (1H, dd), 7.29 (1H, dd), 7.25 (1H, t)1-118.55(1H, s), 8.28(2H, d), 7.95(2H, d), 7.94(1H, d), 7.87(1H, d), 7.79(1H, d), 7.77(1H, d), 7.75(2H, d), 7.69(1H, d), 7.68(1H, dd), 7.64(2H, d), 7.54(1H, d), 7.52(4H, dd), 7.51(7H, dd), 7.41(3H, s), 7.33 (1H, t), 7.25 (1H, t)1-188.93(2H, s), 8.55(1H, d), 8.28(2H, d), 8.12(2H, d), 8.1(1H, d), 8.08(2H, d), 7.94(1H, d), 7.88(3H, d), 7.87(1H, d), 7.82(2H, dd), 7.81(1H, d), 7.79(1H, d), 7.75(1H, dd), 7.72(1H, dd), 7.71(1H, s), 7.68 (1H, t), 7.62 (1H, t), 7.54 (1H, dd), 7.51 (5H, dd), 7.44 (1H, t), 7.41 (2H, d), 7.35 (1H, d), 7.33 (1H, d)1-198.55(1H, s), 7.95(1H, d), 7.94(1H, d), 7.91(1H, d), 7.81(1H, d), 7.79(10H, d), 7.76(1H, d), 7.75(2H, d), 7.68(1H, d), 7.64(1H, dd), 7.62(1H, d), 7.59(1H, d), 7.54(1H, dd), 7.51(9H, dd), 7.44(1H, s), 7.43 (1H, t), 7.41 (4H, t), 7.33 (1H, dd), 7.25 (1H, dd)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 (5H, d)1-228.55(1H, s), 8.12(1H, d), 7.95(1H, d), 7.94(1H, d), 7.85(2H, d), 7.81(1H, d), 7.79(1H, d), 7.75(1H, d), 7.72(1H, d), 7.71(1H, dd), 7.68(1H, d), 7.64(1H, d), 7.63(1H, dd), 7.54(1H, dd), 7.52(4H, s), 7.51 (5H, t), 7.5 (1H, t), 7.41 (2H, dd), 7.33 (1H, dd), 7.29 (1H, t), 7.25 (3H, 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(3H, d), 7.77(1H, d), 7.75(2H, d), 7.68(2H, dd), 7.64(1H, d), 7.63(2H, d), 7.62(1H, dd), 7.57(1H, dd), 7.55(1H, s), 7.54 (1H, t), 7.52 (4H, t), 7.51 (7H, dd), 7.5 (1H, dd), 7.48 (1H, t), 7.44 (1H, d), 7.41 (3H, d), 7.38 (1H, d)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(1H, dd), 7.64(2H, d), 7.63(2H, d), 7.55(1H, dd), 7.54(1H, dd), 7.52(2H, s), 7.51 (6H, t), 7.5 (1H, t), 7.41 (3H, dd), 7.38 (1H, dd), 7.35 (2H, t), 7.33 (1H, d), 7.29 (1H, d), 7.28 (1H, d)1-318.55(1H, s), 8.28(2H, d), 7.94(1H, d), 7.87(1H, d), 7.85(2H, d), 7.81(2H, d), 7.79(1H, d), 7.77(1H, d), 7.7(1H, d), 7.69(1H, dd), 7.68(1H, d), 7.57(1H, d), 7.54(1H, dd), 7.52(4H, dd), 7.51(7H, s), 7.48 (2H, t), 7.41 (3H, t), 7.38 (2H, dd), 7.33 (1H, dd), 7.25 (1H, t)1-428.55(1H, s), 8.28(2H, d), 8(1H, d), 7.94(2H, d), 7.87(1H, d), 7.86(1H, d), 7.82(1H, d), 7.8(1H, d), 7.79(3H, d), 7.77(1H, dd), 7.69(1H, d), 7.68(1H, d), 7.56(1H, dd), 7.54(1H, dd), 7.52(2H, s), 7.51 (7H, t), 7.41 (3H, t), 7.33 (1H, dd), 7.25 (1H, dd)1-658.55(1H, s), 8.12(1H, d), 7.94(1H, d), 7.89(1H, d), 7.81(1H, d), 7.79(1H, d), 7.75(2H, d), 7.72(1H, d), 7.71(1H, d), 7.68(1H, dd), 7.66(1H, d), 7.63(1H, d), 7.62(2H, dd), 7.54(1H, dd), 7.52(2H, s), 7.51 (3H, t), 7.5 (1H, t), 7.44 (2H, dd), 7.41 (1H, dd), 7.38 (1H, t), 7.33 (1H, d), 7.32 (1H, d), 7.29 (1H, d)1-798.55(1H, s), 7.95(1H, d), 7.94(1H, d), 7.89(1H, d), 7.79(6H, d), 7.75(3H, d), 7.68(1H, d), 7.66(1H, d), 7.64(1H, d), 7.62(2H, dd), 7.59(1H, d), 7.54(1H, d), 7.51(5H, dd), 7.44(2H, dd), 7.43(1H, s), 7.41 (2H, t), 7.38 (1H, t), 7.33 (1H, dd), 7.32 (1H, dd), 7.25 (1H, t)1-868.55(2H, s), 8.12(2H, d), 7.94(2H, d), 7.81(2H, d), 7.79(1H, d), 7.72(2H, d), 7.71(2H, d), 7.68(1H, d), 7.63(2H, d), 7.54(1H, dd), 7.52(2H, d), 7.51(3H, d), 7.5(2H, dd), 7.41(1H, dd), 7.33(2H, s), 7.29 (2H, t), 7.25 (2H, t)1-958.55(1H, s), 8.18(1H, d), 8.12(1H, d), 8(1H, d), 7.95(1H, d), 7.94(1H, d), 7.85(1H, d), 7.81(1H, d), 7.79(4H, d), 7.77(1H, dd), 7.75(1H, d), 7.68(1H, d), 7.64(1H, dd), 7.63(1H, dd), 7.59(1H, s), 7.58 (2H, t), 7.54 (1H, t), 7.52 (2H, dd), 7.51 (5H, dd), 7.5 (3H, t), 7.45 (1H, d), 7.43 (1H, d), 7.41 (2H, d)1-1098.55(1H, s), 8.28(2H, d), 8.12(1H, d), 7.95(1H, d), 7.94(1H, d), 7.89(1H, d), 7.79(1H, d), 7.75(3H, d), 7.68(1H, d), 7.66(1H, dd), 7.64(1H, d), 7.63(1H, d), 7.62(2H, dd), 7.54(1H, dd), 7.51(3H, s), 7.5 (1H, t), 7.44 (2H, 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)1-1118.55(1H, s), 8.28(2H, d), 7.95(2H, d), 7.94(1H, d), 7.89(1H, d), 7.87(1H, d), 7.79(1H, d), 7.77(1H, d), 7.75(3H, d), 7.69(1H, dd), 7.68(1H, d), 7.66(1H, d), 7.64(2H, dd), 7.62(1H, dd), 7.54(1H, s), 7.52 (2H, t), 7.51 (5H, t), 7.44 (1H, dd), 7.41 (2H, dd), 7.38 (1H, t), 7.33 (1H, d), 7.32 (1H, d), 7.25 (1H, d)1-1168.55(1H, s), 8.45(1H, d), 8.41(1H, d), 8.2(1H, d), 8.12(1H, d), 7.98(1H, d), 7.94(1H, d), 7.85(4H, d), 7.81(2H, d), 7.79(1H, dd), 7.68(1H, d), 7.63(1H, d), 7.58(1H, dd), 7.54(1H, dd), 7.52(3H, s), 7.51 (6H, t), 7.5 (2H, t), 7.41 (3H, dd), 7.38 (2H, dd), 7.33 (1H, t), 7.29 (1H, d), 7.25 (3H, d)1-1228.55(2H, s), 8.12(2H, d), 7.95(1H, d), 7.94(2H, d), 7.85(2H, d), 7.8(1H, d), 7.79(1H, d), 7.75(1H, d), 7.68(1H, d), 7.66(1H, dd), 7.64(1H, d), 7.63(2H, d), 7.54(1H, dd), 7.52(2H, dd), 7.51(6H, s), 7.5 (3H, t), 7.41 (3H, t), 7.33 (2H, dd), 7.29 (2H, dd), 7.25 (4H, t)1-1318.55(2H, s), 8.28(2H, d), 8.12(1H, d), 7.94(2H, d), 7.89(1H, d), 7.87(1H, d), 7.85(1H, d), 7.81(1H, d), 7.79(1H, d), 7.77(1H, dd), 7.69(1H, d), 7.68(1H, d), 7.63(1H, dd), 7.54(1H, dd), 7.52(2H, s), 7.51 (8H, t), 7.5 (2H, t), 7.41 (4H, dd), 7.38 (1H, dd), 7.33 (2H, t), 7.32 (1H, d), 7.29 (1H, d), 7.25 (2H, d)1-1398.55(1H, s), 8.28(2H, d), 8.18(1H, d), 8.12(1H, d), 8(1H, d), 7.95(1H, d), 7.94(1H, d), 7.87(1H, d), 7.79(1H, d), 7.77(2H, dd), 7.75(1H, d), 7.69(1H, d), 7.68(1H, dd), 7.66(1H, dd), 7.64(1H, s), 7.63 (1H, t), 7.54 (1H, t), 7.52 (4H, dd), 7.51 (10H, dd), 7.5 (1H, t), 7.44 (1H, d), 7.41 (5H, d), 7.38 (1H, d)1-1418.55(1H, s), 8.24(1H, d), 8.12(1H, d), 7.94(1H, d), 7.79(1H, d), 7.7(1H, d), 7.68(1H, d), 7.63(1H, d), 7.57(1H, d), 7.54(1H, dd), 7.52(2H, d), 7.51(3H, d), 7.5(1H, dd), 7.48(1H, dd), 7.41(1H, s), 7.33 (1H, t), 7.29 (1H, t), 7.25 (1H, dd)1-1598.55(1H, s), 8.28(2H, d), 7.94(1H, d), 7.87(1H, d), 7.79(1H, d), 7.77(1H, d), 7.7(1H, d), 7.69(1H, d), 7.68(1H, d), 7.57(1H, dd), 7.54(1H, d), 7.52(2H, d), 7.51(5H, dd), 7.48(2H, dd), 7.41(2H, s), 7.33 (1H, t), 7.25 (1H, t)1-1638.28(2H, s), 7.89(1H, d), 7.66(1H, d), 7.6(1H, d), 7.57(1H, d), 7.52(2H, d), 7.51(4H, d), 7.41(2H, d), 7.38(1H, d), 7.32(1H, dd), 7.25(4H, d)1-1878.28(2H, s), 7.79(1H, d), 7.68(1H, d), 7.54(1H, d), 7.51(3H, d), 7.41(1H, d)1-1928.55(1H, s), 7.94(1H, d), 7.87(1H, d), 7.85(2H, d), 7.79(1H, d), 7.77(1H, d), 7.69(1H, d), 7.68(1H, d), 7.54(1H, d), 7.52(4H, dd), 7.51(5H, d), 7.41(2H, d), 7.33(1H, dd), 7.25(3H, dd)1-2067.89(2H, s), 7.67(2H, d), 7.66(2H, d), 7.63(2H, d), 7.52(4H, d), 7.51(9H, d), 7.5(2H, d), 7.41(5H, d)1-2168.41(2H, s), 8.2(1H, d), 7.89(1H, d), 7.8(1H, d), 7.79(1H, d), 7.75(1H, d), 7.68(1H, d), 7.66(1H, d), 7.62(1H, d), 7.58(2H, dd), 7.54(1H, d), 7.52(2H, d), 7.51(3H, dd), 7.44(1H, dd), 7.41(1H, s), 7.38 (1H, t), 7.32 (1H, t)1-2188.55(1H, s), 8.45(1H, d), 8.41(1H, d), 8.18(1H, d), 7.98(1H, d), 7.94(1H, d), 7.8(1H, d), 7.79(2H, d), 7.68(1H, d), 7.62(1H, dd), 7.58(1H, d), 7.54(1H, d), 7.52(5H, dd), 7.51(7H, dd)1-2377.89(1H, s), 7.79(3H, d), 7.68(1H, d), 7.66(1H, d), 7.6(1H, d), 7.57(1H, d), 7.54(1H, d), 7.51(3H, d), 7.41(1H, d), 7.38(1H, dd), 7.32(1H, d)1-2438.24(1H, s), 7.95(1H, d), 7.89(1H, d), 7.85(1H, d), 7.81(1H, d), 7.79(1H, d), 7.75(2H, d), 7.7(1H, d), 7.68(1H, d), 7.66(1H, dd), 7.64(1H, d), 7.62(1H, d), 7.57(1H, dd), 7.54(1H, dd), 7.52(2H, s), 7.51 (3H, t), 7.48 (1H, t), 7.44 (1H, dd), 7.41 (1H, dd), 7.38 (2H, t), 7.32 (1H, d)1-2678.55(1H, s), 8.28(4H, d), 8.18(1H, d), 8.12(1H, d), 8(1H, d), 7.95(1H, d), 7.94(1H, d), 7.87(1H, d), 7.83(1H, d), 7.79(2H, dd), 7.77(2H, d), 7.75(1H, d), 7.69(1H, dd), 7.68(2H, dd), 7.66(1H, s), 7.64 (1H, t), 7.63 (1H, t), 7.54 (2H, dd), 7.52 (4H, dd), 7.51 (10H, t), 7.5 (1H, d), 7.44 (1H, d), 7.41 (4H, d)1-2728.55(1H, s), 8.28(2H, d), 8.18(1H, d), 8.12(1H, d), 7.94(1H, d), 7.87(1H, d), 7.85(2H, d), 7.79(2H, d), 7.75(1H, d), 7.68(2H, dd), 7.63(1H, d), 7.54(2H, d), 7.52(6H, dd), 7.51(10H, dd), 7.5(2H, s), 7.44 (1H, t), 7.41 (4H, t), 7.38 (1H, dd), 7.33 (2H, dd), 7.29 (2H, t), 7.25 (4H, d)1-2808.55(1H, s), 8.45(1H, d), 8.28(4H, d), 8.18(1H, d), 8.12(1H, d), 7.98(2H, d), 7.94(1H, d), 7.87(1H, d), 7.79(2H, d), 7.75(1H, dd), 7.71(1H, d), 7.68(1H, d), 7.63(1H, dd), 7.54(2H, dd), 7.52(5H, s), 7.51 (10H, t), 7.5 (3H, t), 7.41 (4H, dd), 7.38 (1H, dd), 7.33 (2H, t), 7.29 (2H, d), 7.25 (2H, d)1-2858.55(1H, s), 8.24(1H, d), 8.12(1H, d), 7.94(1H, d), 7.85(2H, d), 7.79(1H, d), 7.7(2H, d), 7.68(1H, d), 7.63(1H, d), 7.57(2H, dd), 7.54(1H, d), 7.52(4H, d), 7.51(5H, dd), 7.5(1H, dd), 7.48(3H, s), 7.41 (2H, t), 7.33 (1H, t), 7.29 (1H, dd), 7.25 (3H, dd)1-2948.55(1H, s), 7.94(1H, d), 7.89(1H, d), 7.85(2H, d), 7.81(1H, d), 7.79(4H, d), 7.72(1H, d), 7.71(1H, d), 7.68(1H, d), 7.66(1H, dd), 7.59(1H, d), 7.54(1H, d), 7.52(2H, dd), 7.51(5H, 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7.51(4H, d), 7.41(1H, d)2-2368.55(1H, s), 8.24(1H, d), 8.12(1H, d), 7.94(1H, d), 7.79(2H, d), 7.7(1H, d), 7.68(2H, d), 7.63(1H, d), 7.57(1H, d), 7.54(2H, dd), 7.52(2H, d), 7.51(4H, d), 7.5(1H, dd), 7.48(1H, dd), 7.41(1H, s), 7.33(1H, t), 7.29 (1H, t), 7.25(1H, dd),2-2598.55(1H, s), 8.28(1H, d), 8.12(1H, d), 8.09(1H, d), 7.94(1H, d), 7.79(1H, d), 7.68(1H, d), 7.66(3H, d), 7.63(1H, d), 7.54(1H, dd), 7.52(4H, d), 7.51(6H, d), 7.5(1H, dd), 7.46(1H, dd), 7.41(2H, s), 7.33 (1H, t), 7.29 (1H, t), 7.25 (1H, dd)2-2648.55(2H, s), 7.95(1H, d), 7.94(2H, d), 7.89(1H, d), 7.88(1H, d), 7.79(7H, d), 7.75(2H, d), 7.74(1H, d), 7.68(1H, d), 7.66(1H, dd), 7.64(1H, d), 7.59(2H, d), 7.54(1H, dd), 7.52(2H, dd), 7.51(7H, s), 7.43 (2H, t), 7.38 (1H, t), 7.33 (2H, dd), 7.32 (1H, dd), 7.25 (2H, t)2-2737.98(1H, s), 7.85(2H, d), 7.79(1H, d), 7.75(2H, d), 7.7(1H, d), 7.68(1H, d), 7.57(2H, d), 7.54(1H, d), 7.52(2H, d), 7.51(5H, dd), 7.48(2H, d), 7.41(2H, d), 7.25(2H, dd), 7.19(2H, dd)2-2877.95(1H, s), 7.85(1H, d), 7.81(1H, d), 7.79(2H, d), 7.75(1H, d), 7.68(2H, d), 7.64(1H, d), 7.54(2H, d), 7.52(2H, d), 7.51(4H, dd), 7.41(1H, d), 7.4(1H, d), 7.38(1H, dd), 7.30(3H, m)2-2928.28(3H, 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(2H, d), 7.64(1H, dd), 7.54(4H, d), 7.52(2H, d), 7.46(1H, dd), 7.25 (1H, t)2-2958.28(2H, s), 7.89(1H, d), 7.79(1H, d), 7.68(2H, d), 7.66(1H, d), 7.6(1H, d), 7.57(1H, d), 7.54(4H, d), 7.52(2H, d), 7.51(1H, dd), 7.43(1H, d), 7.41(2H, d), 7.38(1H, dd), 7.32(1H, dd), 7.29 (2H, m)2-3018.55(2H, s), 8.12(1H, d), 7.94(2H, d), 7.8(1H, d), 7.79(5H, d), 7.75(1H, d), 7.68(2H, d), 7.66(1H, d), 7.63(1H, d), 7.62(1H, dd), 7.59(1H, d), 7.54(2H, d), 7.51(2H, dd), 7.5(2H, dd), 7.44(3H, m), 7.43 (1H, t), 7.41 (2H, t), 7.33 (2H, dd), 7.29 (1H, dd), 7.25 (2H, t)2-3128.35 (3H, dd), 8.28(2H, s), 7.79(2H, d), 7.68(2H, d), 7.54(2H, d), 7.51(4H, d), 7.41(1H, d), 7.36 (1H, d)2-3307.98(1H, s), 7.85(3H, m), 7.79(1H, d), 7.75(2H, d), 7.7(1H, d), 7.68(1H, d), 7.57(2H, d), 7.54(1H, d), 7.52(2H, d), 7.51(5H, dd), 7.48(2H, d), 7.41(2H, d), 7.25(2H, dd), 7.19(2H, dd).

[0468]

[0469] 화합물번호FD-MS화합물번호FD-MS1-9m / z=640.75(C 45 H 28 N4O)1-11m / z=716.26(C 51 H 32 N4O)1-18m / z=867.00(C 63 H 38 N4O)1-19m / z=869.02(C 63 H 40 N4O)1-21m / z=790.91(C 57 H 34 N4O)1-22m / z=716.83(C 51 H 32 N4O)1-24m / z=756.89(C 54 H 36 N4O)1-26m / z=897.01(C 64 H 38 N4O)1-31m / z=792.92(C 57 H 36 N4O)1-42m / z=732.89(C 51 H 32 N4S)1-65m / z=730.81(C 51 H 30 N4O2)1-79m / z=806.91(C 57 H 34 N4O2)1-86m / z=729.82(C 51 H 31N5O)1-95m / z=882.02(C 63 H 39 N5O)1-109m / z=730.81(C 51 H 30 N4O2)1-111m / z=806.91(C 54 H 34 N4O2)1-116m / z=822.97(C 57 H 34 N4OS)1-122m / z=805.92(C 57 H 35 N5O)1-131m / z=805.92(C 57 H 35 N5O)1-139m / z=882.02(C 63 H 39 N5O)1-141m / z=727.89(C 51 H 22 D 11 N4O)1-159m / z=803.99(C 57 H 25 D 11 N4O)1-163m / z=728.90(C 51 H 20 D 12 N4O)1-187m / z=739.97(C 51 H9D 23 N4O)1-192m / z=803.99(C 57 H 25 D 11 N4O)1-206m / z=899.10(C 63 H 22 D 16 N4O2)1-216m / z=835.05(C 57 H 22 D 12 N4OS)1-218m / z=834.04(C 57 H 23 D 11 N4OS)1-237m / z=826.04(C 57 H 15 D 20 N5O)1-243m / z=814.95(C 57 H 26 D8N4O2)1-267m / z=767.02(C 51 H 10 D 21N5S)1-272m / z=820.01(C 57 H 21 D 14 N5O)1-280m / z=753.94(C 51 H 23 D8N5O)1-285m / z=702.28(C 51 H 34 N4)1-294m / z=716.26(C 51 H 32 N4O)1-312m / z=708.32(C 51 H 24 D8N4)1-317m / z=732.36(C 51 H 16 D 16 N4O)1-329m / z=702.28(C 51 H 34 N4)1-340m / z=814.95(C 57 H 28 D8N4O2)1-341m / z=725.31(C 51 H 23 D9N4O)1-347m / z=725.31(C 51 H 23 D9N4O)1-356m / z=734.37 (C 51 H 14 D 18 N4O)1-360m / z=896.39(C 63 H 24 D 14 N4O2)1-363m / z=831.30(C 57 H 25 D9N4OS)1-369m / z=823.39(C 57 H 18 D 17 N5O)1-372m / z=813.31(C 57 H 27 D7N4O2)1-390m / z=730.35(C 51 H 18 D 14 N4O)1-380m / z=762.34(C 51 H 14 D 17 N5S)1-382m / z=817.36(C 57 H 23 D 12N5O)2-4m / z=805.92(C 57 H 35 N5O)2-15m / z=958.11(C 69 H 43 N5O)2-18m / z=958.11(C 69 H 43 N5O)2-26m / z=805.92(C 57 H 35 N5O)2-36m / z=882.02(C 63 H 36 N5O)2-48m / z=898.08(C 63 H 39 N5S)2-65m / z=896.00(C 63 H 37 N5O2)2-76m / z=895.02(C 63 H 38 N6O)2-82m / z=822.02(C 57 H 19 D 16 N5O)2-95m / z=981.25(C 69 H 20 D 23 N5O)2-100m / z=894.09(C 63 H 27 D 12 N5O)2-110m / z=822.02(C 57 H 19 D 16 N5O)2-116m / z=981.25(C 69 H 20 D 23 N5O)2-125m / z=912.10(C 63 H 21 D 16 N5O2)2-135m / z=903.06(C 63 H 30 D8N6O)2-137m / z=979.16(C 69 H 34 D8N6O)2-150m / z=791.30(C 57 H 37 N5)2-153m / z=789.29(C 57 H 35 N5)2-158m / z=907.37(C 66 H 45N5)2-176m / z=791.30(C 57 H 37 N5)2-183m / z=745.23(C 51 H 31 N5S)2-187m / z=881.32(C 63 H 39 N5O)2-220m / z=815.46(C 57 H 13 D 24 N5)2-236m / z=803.38(C 57 H 25 D 12 N5)2-259m / z=879.41(C 63 H 29 D 12 N5)2-264m / z=958.11(C 69 H 43 N5O)2-273m / z=883.13(C 63 H 26 D 15 N5)2-287m / z=977.47(C 69 H 23 D 20 N5O)2-292m / z=819.37(C 57 H 21 D 14 N5O)2-295m / z=977.47(C 69 H 23 D 20 N5O)2-312m / z=811.43(C 57 H 17 D 20 N5)2-330m / z=881.42(C 63 H 27 D 14 N5O)2-301m / z=978.39(C 69 H 35 D7N6O)

[0470]

[0471] Preparation Example 3. Preparation of Compound 3-1

[0472]

[0473]

[0474] Preparation Example 3-1. Preparation of Compound R-1

[0475] 5,8-dihydroindolo[2,3-c]carbazole (20g, 78.03mmol), bromobenzene (12.2g, 78.03mmol), 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.

[0476] 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 81%) of compound R-1, a white solid.

[0477]

[0478] Preparation Example 3-2. Preparation of Compound 3-1

[0479] Compound R-1 (20g, 60.24mmol), 4-bromo-1,1'-biphenyl (14g, 60.24mmol), 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.

[0480] 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 chlorobenzene to obtain 17 g (yield 63%) of compound 3-1, a white solid.

[0481]

[0482] The target compounds of Table 5 below were synthesized by the same method as in Preparation Example 3, except that Compound a of Table 5 below was used instead of [2,3-c]carbazole as 5,8-dihydroindole, 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.

[0483]

[0484]

[0485]

[0486]

[0487]

[0488] Preparation Example 4. Preparation of Compound 3-41

[0489]

[0490] Compound 3-1 (20g, 41.27mmol) 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.

[0491] 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 3-41, a white solid (yield 92%, 100% D-substitution rate).

[0492]

[0493] The target compounds of Table 6 below were synthesized by preparing them in the same manner as in Preparation Example 4, except that compound d of Table 6 below was used instead of compound 3-1 in Preparation Example 4 above. Yield refers to the yield of the final reaction.

[0494]

[0495]

[0496]

[0497]

[0498]

[0499] 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).

[0500]

[0501] Compound number 11H NMR (CDCl3, 300MHz) 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) 3-88.55 (2H, s), 7.95 (1H, d), 7.94 (2H, d), 7.89 (1H, d), 7.79 (4H, d), 7.7 (1H, d), 7.68 (4H, d) 7.66(1H, d), 7.64(1H, d), 7.63(1H, dd), 7.62(2H, d), 7.57(1H, d), 7.52(4H, dd), 7.51(4H, dd), 7.48(2H, s), 7.41(2H, t), 7.33(2H, t), 7.31(1H, dd), 7.25(2H, dd)3-158.55(2H, s), 8.09(2H, d), 7.94(2H, d), 7.63(1H, d), 7.52(6H, d), 7.51(9H, d), 7.46(2H, d), 7.41(4H, d) 7.33(2H, d), 7.31(1H, dd), 7.25(7H, d)3-178.93(1H, s), 8.9(2H, d), 8.55(2H, d), 8.12(1H, d), 8.1(2H, d), 7.94(2H, d), 7.9(1H, d), 7.88(1H, d), 7.82(1H, d), 7.8(2H, dd), 7.63(1H, d), 7.58(2H, d), 7.5(2H, dd), 7.45(1H, dd), 7.41(2H, s), 7.33 (4H, t)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 (dd, 2H), 7.81 (s, 1H), 7.91-7.95 (m, 3H), 7.99 (dd, 2H), 8.56 (dd, 2H)3-43 with a deuterium substitution rate of 100%. 1H NMR peak 없음3-497.65 (dd, 2H), 7.75 (d, 2H)3-537.26 (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)3-757.59 (dd, 1H), 8.12 (m, 2H)4-47.21-7.23 (m, 4H), 7.25 (dd, 1H), 7.27-7.30 (m, 5H), 7.32-7.36 (m, 6H), 7.42 (s. 1H), 7.55 (dd, 2H), 7.61-7.62 (m, 4H), 7.65 (s, 1H), 7.69-7.70 (m, 3H), 7.88 (dd, 1H), 8.02 (s, 1H), 8.23 ​​(dd, 2H), 8.51 (s, 1H)4-207.20 (t, 2H), 7.23-7.26 (m, 4H), 7.35-7.37 (m, 5H), 7.41 (s, 2H), 7.49-7.50 (m, 3H), 7.59 (s, 1H), 7.72-7.75 (m, 3H), 7.80-7.81 (m, 4H), 7.91-7.95 (m, 4H), 7.99 (dd, 2H), 8.56 (dd, 2H), 8.61 (d, 2H) 4-267.20-7.23 (m, 5H), 7.25-7.26 (m, 3H), 7.30 (dd, 1H), 7.35-7.37 (m, 3H), 7.40-7.41 (m, 5H), 7.45 (d, 2H), 7.50 (dd, 2H), 7.59-7.62 (m, 3H), 7.75 (d, 2H), 7.91-7.95 (m, 4H), 7.99 (dd, 2H), 8.01 (t, 2H), 8.56 (dd, 2H) 4-527.41 (s, 1H)4-54중수소 치환율 100%로 1 H NMR peak 없음4-687.32 (dd, 2H), 7.50 (m, 2H), 8.01 (dd, 2H)

[0502]

[0503] Compound Number FD-MS Compound Number FD-MS3-6 m / z=560.70(C 42 H 28 N2)3-8m / z=626.26(C 48 H 32 N2)3-15m / z=626.26(C 48 H 32 N2)3-17m / z=558.21(C 42 H 26 N2)3-27m / z=636.80(C 48 H 32 N2)3-37m / z=560.70(C 42 H 28 N2)3-43m / z=746.10(C 54 H3D 33 N2)3-49m / z=664.46(C 48 H4D 28 N2)3-53m / z=663.95(C 48 H5D 27 N2)3-55m / z=663.96(C 48 H5D 27 N2)3-64m / z=583.83(C 42 H5D 23 N2)3-75m / z=587.87(C 42 HD 27 N2)4-4m / z=636.26(C 48 H 32 N2)4-20m / z=710.27(C 54 H 34 N2)4-26m / z=712.29(C 54 H 36 N2)4-52m / z=667.45(C 48 HD 31 N2)4-54m / z=680.42(C 48 D 30 N2O)4-68m / z=742.48(C 54 H6D 30 N2)

[0504]

[0505] Experimental Example 1.

[0506] Experimental Example 1-1. Fabrication of an Organic Light-Emitting Device

[0507] 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.

[0508] 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).

[0509] A light-emitting layer was deposited on top of it as follows. The light-emitting layer used a compound listed in Table 9 below as the host, and Ir(ppy)3(bpmp) as the green phosphorescent dopant, and was deposited to a thickness of 370 Å by doping the host with 6% Ir(ppy)3(bpmp).

[0510] 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.

[0511] Meanwhile, all organic compounds required for OLED device fabrication are 10 each for each material -6 ~10 -8It was purified by vacuum sublimation under torr and used for fabricating OLEDs (Organic Light Emitting Devices).

[0512]

[0513] Experimental Example 1-2. Driving voltage and luminous efficiency of an organic light-emitting diode

[0514] 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.

[0515] The above T 90 represents the lifespan (unit: hours) of the time it takes to reach 90% of the initial brightness.

[0516] In addition, the brightness of the organic light-emitting diode was measured according to the viewing angle from a 45-degree side, and the results are shown in Table 10 below.

[0517]

[0518] Compound Ratio (N1:N2:P1:P2) Driving Voltage (V) Luminous Efficiency (cd / A) Chromatic Coordinates Lifetime (T 90)N1N2P1P2 Comparative Example 11-9---10:-:-:-4.8952.5Green16 Comparative Example 2-2-4---:10:-:-5.0156.7Green19 Comparative Example 3--3-6--:-:10:-5.9933.8Green15 Comparative Example 41-9-3-8-4:-:6:-4.0869.5Green119 Comparative Example 5-2-153-17--:4:6:-4.2670.9Green125 Comparative Example 61-1092-110--5:5:-:-5.1353.3Green18 Example 11-92-43-6-2:2:6:-3.15121.5Green205 Example 21-112-153-8-2:2:6:-3.16126.4Green215 Example 31-181-93-49-2:2:6:-3.35104.5Green402 Example 41-191-1163-53-2:2:6:-3.22101.6Green389 Example 51-211-1923-55-2:2:6:-3.10105.8Green409 Example 61-222-263-15-2:2:6:-3.28116.8Green255 Example 71-242-1503-6-2:2:6:-3.11117.0Green288 Example 81-262-1583-8-2:2:6:-2.98111.9Green296 Example 91-312-363-17-2:2:6:-3.33115.5Green261 Example 101-422-483-27-2:2:6:-3.56108.2Green299 Example 111-652-653-37-2:2:6:-3.09130.2Green211 Example 121-792-823-43-2:2:6:-3.10129.5Green405 Example 131-862-953-49-2:2:6:-3.61110.1Green415 Example 141-952-1003-53-2:2:6:-3.59106.8Green416 Example 151-1092-1103-55-2:2:6:-3.34118.2Green430 Example 161-1112-1163-64-2:2:6:-3.39117.5Green425 Example 171-1162-1763-15-2:2:6:-3.35120.0Green269 Example 181-1412-1253-71-2:2:6:-3.01125.7Green450 Example 191-1592-763-75-2:2:6:-2.99126.3Green453 Example 201-1632-1353-6-2:2:6:-3.03122.8Green286 Example 211-1872-1373-8-2:2:6:-3.13129.0Green271 Example 221-1922-43-15-2:2:6:-3.12130.1Green258 Example 231-2062-1873-6-2:2:6:-3.36102.3Green222 Example 241-2162-153-17-2:2:6:-3.44105.5Green238 Example 251-2182-2203-53-2:2:6:-3.10113.6Green375 Example 261-2182-183-55-2:2:6:-3.13114.1Green369 Example 271-2372-263-27-2:2:6:-3.76100.2Green265 Example 281-2432-363-37-2:2:6:-3.26116.3Green269 Example 291-2852-2593-27-2:2:6:-3.10125.8Green280 Example 301-2941-93-49-2:2:6:-3.11124.4Green448 Example 311-3121-1093-64-2:2:6:-3.15122.1Green452 Example 321-3172-1503-75-2:2:6:-3.21120.9Green460 Example 331-1312-483-43-2:2:6:-3.33111.9Green411 Example 341-1392-653-49-2:2:6:-3.51112.2Green395 Example 351-2672-823-53-2:2:6:-3.66115.4Green461 Example 361-2722-953-55-2:2:6:-3.49113.9Green386 Example 371-2802-1003-64-2:2:6:-3.60108.7Green365 Example 381-92-153-6-2:2:6:-3.15126.9Green275 Example 391-222-653-17-2:2:6:-3.19124.5Green261 Example 401-1092-823-27-2:2:6:-3.14128.8Green387 Example 411-1592-1253-49-2:2:6:-3.21123.3Green454 Example 421-1872-1353-64-2:2:6:-3.46118.9Green466 Example 431-1922-1373-75-2:2:6:-3.50120.2Green481 Example 442-42-1503-6-2:2:6:-3.18129.6Green320 Example 452-152-1583-8-2:2:6:-3.05124.2Green277 Example 462-182-1763-49-2:2:6:-3.39120.9Green449 Example 472-262-1873-53-2:2:6:-3.41119.5Green430 Example 482-652-2203-55-2:2:6:-3.55129.5Green455 Example 492-822-2363-43-2:2:6:-3.51123.3Green460 Example 501-92-1533-17-2:2:6:-3.42101.2Green270 Example 512-652-1833-43-2:2:6:-3.45105.6Green288 Example 521-3292-653-27-2:2:6:-3.39106.2Green250 Example 532-652-2733-64-2:2:6:-3.40111.5Green389 Example 541-3561-243-4-682:2:-:63.23109.0Green301 Example 551-369-3-533-554:-:1:52.98103.6Green405 Example 561-2062-3123-17-1:3:6:-3.36120.2Green268 Example 572-822-135-4-541:3:-:63.46128.9Green436 Example 58-2-2363-754-20-:4:1:53.05109.5Green295 Example 591-109-3-494-43:-:5:12.96115.9Green316 Example 60-2-1373-644-54-:3:2:43.61110.8Green453 Example 611-280-3-83-754:-:1:52.97109.9Green378 Example 62-2-824-204-68-:4:5:13.15112.3Green385.

[0519]

[0520] Compound Ratio (N1:N2:P1:P2) 0° Luminous Efficiency (cd / A) 45° Luminous Efficiency (cd / A) 45° Side Efficiency / Front Efficiency * 100(%) N1 N2 P1 P2 Comparative Example 11-9---10:-:-:-5 2.5 15.6 29.7 Comparative Example 3--3-6--:-10:-3 3.8 7.4 7 22.1 Comparative Example 41-9-3-8-4:-:6:-6 9.5 25.6 36.8 Comparative Example 5-2-15 3-17--:4:6:-7 0.9 26.3 37.1 Example 51-21 1-19 23-55-2:2:6:-10 5.8 43.3 40.9 Example 191-1592-763-75-2:2:6:-126.352.041.2 Example 291-2852-2593-27-3:1:6:-125.851.340.8 Example 321-3172-1503-75-3:1:6:-120.950.942.1 Example 411-1592-1253-49-1:3:6:-123.351.341.6 Example 462-182-1763-49-2:2:6:-120.949.941.3 Example 541-3561-243-4-682:2:-:6109.043.740.1 Example 561-2062-3123-17-1:3:6:-120.250.540.0 Example 60-2-1373-644-54-:3:2:5110.845.040.6 Example 62-2-824-204-68-:3:6:1122.350.040.9

[0521]

[0522] In the results of Table 9 above, an organic light-emitting device comprising two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formulas 1 and 2 as a host of the light-emitting layer, and one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formulas 3 and 4, showed results of low driving voltage and excellent luminous efficiency and lifetime characteristics. In addition, an organic light-emitting device comprising one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formulas 1 and 2 as a host of the light-emitting layer, and two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formulas 3 and 4, also showed results of low driving voltage and excellent luminous efficiency and lifetime characteristics.

[0523] Specifically, an organic light-emitting device comprising two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2; and one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 3 and Chemical Formula 4 showed a result in reduced driving voltage due to smooth electron injection caused by two n-hosts, and various exciplex forms were formed within the emitting layer, reducing exciton loss due to energy level gaps, resulting in excellent luminous efficiency and lifetime of the organic light-emitting device.

[0524] In addition, an organic light-emitting device comprising one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formulas 1 and 2; and two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formulas 3 and 4, showed a result in which the driving voltage of the organic light-emitting device was reduced by resolving the phenomenon of holes being trapped in dopants and forming a wide light-emitting zone, by combining the two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formulas 3 and 4, which are p-hosts with different mobilities and energy levels. Furthermore, similar to the organic light-emitting device mixing the two types of n-hosts, various exciplex forms were formed within the light-emitting layer, showing excellent results in luminous efficiency and lifespan.

[0525] The comparative example comprises one or two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formulas 1 to 34 as the host of the light-emitting layer. An organic light-emitting device comprising one or two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formulas 1 and 2 as the n-Host exhibited a high driving voltage because holes could not be injected into the light-emitting layer, and showed poor luminous efficiency and lifespan due to charge imbalance. An organic light-emitting device comprising one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formulas 1 and 2 as the n-Host and one heterocyclic compound represented by Chemical Formula 3 as the p-Host showed improved results compared to an organic light-emitting device containing only the n-Host due to the resolution of charge imbalance, but exhibited poor results in driving voltage, luminous efficiency, and lifespan compared to the example.

[0526] In the results of Table 10 above, it was confirmed that an organic light-emitting device comprising two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formulas 1 and 2; and one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formulas 3 and 4, and an organic light-emitting device comprising one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formulas 1 and 2; and two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formulas 3 and 4, induces isotropic light emission within the light-emitting layer and increases light efficiency at a 45-degree angle compared to an organic light-emitting device of a comparative example comprising one or two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formulas 1 to 4. The luminance viewing angle is an essential element for various types of panel configurations, and materials with excellent viewing angles have value for use in the fabrication of foldable or large-area panels.

[0527]

[0528] [Explanation of the symbol]

[0529] 100: Substrate

[0530] 200: Anode

[0531] 300: Organic layer

[0532] 301: Hole injection layer

[0533] 302: Precision Transport Layer

[0534] 303: Emissive layer

[0535] 304: Main barrier layer

[0536] 305: Electron transport layer

[0537] 306: Electron injection layer

[0538] 400: Cathode

Claims

1. 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, At least one layer among the above organic layers is (1) Two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by the following chemical formulas 1 and 2; and one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by the following chemical formulas 3 and 4, or (2) one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by the following chemical formulas 1 and 2; and two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by the following chemical formulas 3 and 4, comprising an organic light-emitting device: [Chemical Formula 1] [Chemical Formula 2] [Chemical Formula 3] [Chemical Formula 4] In the above chemical formulas 1 to 4, The above R1 to R3, R11 to R15, R21, R22, R31 and R32 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)R101R102; -SiR101R102R103; Selected from the group consisting of -NR101R102, or a C6 to C60 aromatic hydrocarbon ring that is substituted or unsubstituted by combining two or more adjacent groups; or forming a substituted or unsubstituted C2 to C60 heterocyclic ring, wherein R101, R102, and R103 are the same or different from each other and each independently comprises a 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 to a3, c1 to c5 and e2 are the same or different from each other, and each is independently an integer from 0 to 4, and The above e1 is an integer from 0 to 6, and The above g1 and g2 are the same or different from each other, and each is independently an integer from 0 to 7, and The above Ar1, Ar2, Ar11, Ar21, Ar22, Ar31, and Ar32 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 L1, L2, L12, L21, L22, L31 and L32 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 L11 is a substituted or unsubstituted C6 to C60 arylene group, and The above b1, b2, d1, d2, f1, f2, h1, and h2 are the same or different from each other, and each is independently an integer from 0 to 5, and If Ar1 is a substituted or unsubstituted carbazolyl group, L1 is a direct bond; or a substituted or unsubstituted C2 to C60 heteroarylene group, and if Ar2 is a substituted or unsubstituted carbazolyl group, L2 is a direct bond; or a substituted or unsubstituted C2 to C60 heteroarylene group.

2. In Paragraph 1, An organic light-emitting device in which the above R2, R3 and R12 to R15 are the same or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

3. In Paragraph 1, The heterocyclic compound represented by the above chemical formula 1 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%, and The heterocyclic compound represented by the above chemical formula 2 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%, and The 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%, and An organic light-emitting device in which the heterocyclic compound represented by the above chemical formula 4 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%.

4. In Paragraph 1, An organic light-emitting device wherein the heterocyclic compound represented by the above chemical formula 1 is represented by any one of the following compounds: .

5. In Paragraph 1, An organic light-emitting device wherein the heterocyclic compound represented by the above chemical formula 2 is represented by any one of the following compounds: .

6. In Paragraph 1, 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.

7. In Paragraph 1, An organic light-emitting device wherein the heterocyclic compound represented by the above chemical formula 3 is represented by any one of the following compounds: .

8. In Paragraph 1, An organic light-emitting device wherein the heterocyclic compound represented by the above chemical formula 4 is represented by any one of the following compounds: .

9. In Paragraph 1, The above organic layer includes a light-emitting layer, and The light-emitting layer comprises (1) two types of heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2; and one type of heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 3 and Chemical Formula 4, or (2) one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by the above chemical formulas 1 and 2; and two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by the above chemical formulas 3 and 4, comprising an organic light-emitting device.

10. In Paragraph 1, 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 comprises (1) two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2; and one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 3 and Chemical Formula 4, or (2) one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by the above chemical formulas 1 and 2; and two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by the above chemical formulas 3 and 4, comprising an organic light-emitting device.

11. In Paragraph 10, The above host material is (1-1) Two types of heterocyclic compounds represented by the above chemical formula 1; and one type of heterocyclic compound selected from the group consisting of heterocyclic compounds represented by the above chemical formulas 3 and 4, (1-2) comprising two types of heterocyclic compounds represented by the above chemical formula 2; and one type of heterocyclic compound selected from the group consisting of heterocyclic compounds represented by the above chemical formulas 3 and 4, or (1-3) An organic light-emitting device comprising one heterocyclic compound represented by the above chemical formula 1; one heterocyclic compound represented by the above chemical formula 2; and one heterocyclic compound selected from the group consisting of the above chemical formulas 3 and 4.

12. In Paragraph 10, The above host material is (2-1) One heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2; and two heterocyclic compounds represented by Chemical Formula 3, (2-2) One heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2; and two heterocyclic compounds represented by Chemical Formula 4, or (2-3) An organic light-emitting device comprising: one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2; one heterocyclic compound represented by Chemical Formula 3; and one heterocyclic compound represented by Chemical Formula 4.

13. In Paragraph 1, 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.

14. A composition for an organic layer comprising: two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Formula 1 and Formula 2 of Claim 1; and one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Formula 3 and Formula 4.

15. In Paragraph 14, A composition for an organic layer, wherein the weight ratio of two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2 to one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 3 and Chemical Formula 4 is 1:9 to 9:

1.

16. A composition for an organic layer comprising: one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Formula 1 and Formula 2 of Claim 1; and two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Formula 3 and Formula 4.

17. In Paragraph 16, A composition for an organic layer, wherein the weight ratio of one heterocyclic compound selected from the group consisting of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2 and two heterocyclic compounds selected from the group consisting of heterocyclic compounds represented by Chemical Formula 3 and Chemical Formula 4 is 1:9 to 9:1.

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