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

Abstract

The present specification relates to a heterocyclic compound represented by Chemical Formula 1, an organic light-emitting device including the heterocyclic compound, a method for producing the same, and a composition for an organic layer.

Description

[Technical Field]

[0001] This application claims the benefit of the filing date of Korean Patent Application No. 10-2019-0177328, filed with the Korean Intellectual Property Office on December 30, 2019, the entire contents of which are incorporated herein by reference.

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

[0003] An organic electroluminescent device is a type of self-luminous display device, and has advantages such as a wide viewing angle, excellent contrast, and fast response speed.

[0004] An organic light-emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to an organic light-emitting device with this 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.

[0005] The material of the organic thin film may have a light-emitting function as needed. For example, the material of the organic thin film may be a compound that can constitute an emitting layer by itself, or a compound that functions as a host or dopant in a host-dopant emitting layer. In addition, the material of the organic thin film may be a compound that functions as a hole injection, hole transport, electron block, hole block, electron transport, electron injection, etc.

[0006] To improve the performance, lifetime or efficiency of organic light-emitting devices, there is a continuing need to develop materials for organic thin films.

[0007] Research is needed into organic light-emitting devices that contain compounds that can satisfy the requirements for usable materials in organic light-emitting devices, such as appropriate energy levels, electrochemical stability, and thermal stability, and that have chemical structures that can fulfill the various roles required in organic light-emitting devices depending on the substituents. [Prior art documents] [Patent documents]

[0008] [Patent Document 1] U.S. Patent No. 4,356,429 Summary of the Invention [Problem to be solved by the invention]

[0009] The present invention provides a heterocyclic compound, an organic light-emitting device containing the heterocyclic compound, a method for producing the same, and a composition for an organic layer. [Means for solving the problem]

[0010] In one embodiment of the present application, there is provided a heterocyclic compound represented by the following Chemical Formula 1:

[0011] [ka] In the above Chemical Formula 1, X is O; or S; N-Het is a substituted or unsubstituted monocyclic or polycyclic heterocyclic group containing one or more N atoms; Ar1 and Ar2 are the same or different and each independently represent a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; or -SiRR'R'', R3 to R5 are the same or different and each independently represent a hydrogen atom; a deuterium atom; a halogen atom; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; -SiRR'R'' and -NRR'; or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 aliphatic or aromatic heterocycle; L1 to L3 are the same or different and each independently represent a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group; wherein R, R', and R'' are the same or different and each independently represent a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; p and q are integers of 1 to 4, b, m, and n are integers of 0 to 4, a is an integer from 0 to 3, When p, q, a, b, m, and n are 2 or more, the substituents in parentheses may be the same or different.

[0012] Furthermore, according to one embodiment of the present application, there is provided an organic light-emitting device comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers contains a heterocyclic compound represented by Chemical Formula 1.

[0013] Furthermore, one embodiment of the present application provides an organic light-emitting device, wherein the organic material layer containing the heterocyclic compound of Chemical Formula 1 above further contains a heterocyclic compound represented by Chemical Formula A below.

[0014] [ka] In the above chemical formula A, Rc and Rd are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, a halogen group, -CN, a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C2 to C60 alkenyl group, a substituted or unsubstituted C2 to C60 alkynyl group, a substituted or unsubstituted C1 to C60 alkoxy group, a substituted or unsubstituted C3 to C60 cycloalkyl group, a substituted or unsubstituted C2 to C60 heterocycloalkyl group, a substituted or unsubstituted C6 to C60 aryl group, a substituted or unsubstituted C2 to C60 heteroaryl group, -SiR201R202R203; -P(=O)R201R202; and -NR201R202, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle; Ra and Rb are the same or different and each independently represent a substituted or unsubstituted C6 to C60 aryl group; -SiR201R202R203; -P(=O)R201R202; or a substituted or unsubstituted C2 to C60 heteroaryl group; R201, R202, and R203 are the same or different and each independently represent hydrogen; deuterium; -CN; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; r and s are integers from 0 to 7, When r and s are 2 or more, the substituents in parentheses may be the same or different.

[0015] In addition, another embodiment of the present application provides a composition for an organic layer of an organic light-emitting device, which comprises a heterocyclic compound represented by Chemical Formula 1 and a heterocyclic compound represented by Chemical Formula A.

[0016] Finally, one embodiment of the present application provides a method for manufacturing an organic light-emitting device, comprising the steps of: preparing a substrate; forming a first electrode on the substrate; forming one or more organic material layers on the first electrode; and forming a second electrode on the organic material layers, wherein the step of forming the organic material layers includes forming one or more organic material layers using a composition for an organic material layer according to one embodiment of the present application. [Effects of the Invention]

[0017] The compounds described herein can be used as organic layer materials in organic light-emitting devices. The compounds can serve as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, and the like in organic light-emitting devices. In particular, the compounds can be used as light-emitting layer materials in organic light-emitting devices. For example, the compounds can be used alone as light-emitting materials, or two types of the compounds can be used together as light-emitting materials or as host materials in the light-emitting layer.

[0018] In particular, the heterocyclic compound according to the present application has substituents Ar1 and Ar2 at the 4-position of each benzene ring of dibenzofuran, and has the characteristic of increasing thermal stability by blocking electronically weak positions of dibenzofuran with the substituents, thereby particularly improving the lifetime of organic light-emitting devices containing the compound.

[0019] In particular, the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula A may be simultaneously used as materials for the light-emitting layer of an organic light-emitting device, which can reduce the driving voltage of the device, improve light efficiency, and particularly improve the life characteristics of the device due to the thermal stability of the compounds. [Brief explanation of the drawings]

[0020] [Figure 1] 1 is a diagram schematically illustrating a stack structure of an organic light-emitting device according to an embodiment of the present application. [Figure 2] 1 is a diagram schematically illustrating a stack structure of an organic light-emitting device according to an embodiment of the present application. [Figure 3] 1 is a diagram schematically illustrating a stack structure of an organic light-emitting device according to an embodiment of the present application. DETAILED DESCRIPTION OF THE INVENTION

[0021] The present application will be described in detail below.

[0022] In this specification, when "no substituent is shown in the chemical formula or compound structure," it means that a hydrogen atom is bonded to a carbon atom. However, deuterium ( 2 H, Deuterium) is an isotope of hydrogen, so some hydrogen atoms may be deuterium.

[0023] In one embodiment of the present application, "when no substituent is shown in the chemical formula or compound structure," can mean that all positions substitutable as substituents are hydrogen or deuterium. In other words, in the case of deuterium, which is an isotope of hydrogen, some hydrogen atoms may be deuterium, which is an isotope of hydrogen, and in this case, the content of deuterium may be 0% to 100%.

[0024] In one embodiment of the present application, in "when no substituent is shown in the chemical formula or compound structure," hydrogen and deuterium may be used in a mixed state in the compound unless deuterium is clearly excluded, such as when the deuterium content is 0% or the hydrogen content is 100%. That is, when it is expressed that "substituent X is hydrogen," it can mean a state in which hydrogen and deuterium are mixed, such as when the hydrogen content is 100% or the deuterium content is 0%, without excluding deuterium.

[0025] In one embodiment of the present application, deuterium is one of the isotopes of hydrogen and is an element having a deuteron consisting of one proton and one neutron as an atomic nucleus, and can be represented as hydrogen-2, and its element symbol can also be written as D or 2H.

[0026] In one embodiment of the present application, isotopes refer to atoms with the same atomic number (Z) but different mass numbers (A). Isotopes can also be interpreted as elements with the same number of protons but different numbers of neutrons.

[0027] In one embodiment of the present application, the content T% of a specific substituent can be defined as T2 / T1×100=T%, where T1 is the total number of substituents that the base compound may have and T2 is the number of specific substituents among them.

[0028] That is, in one example: [ka] In a phenyl group represented by the formula, a deuterium content of 20% can be expressed as 20% when the total number of substituents that the phenyl group can have is 5 (T1 in the formula), of which the number of deuterium is 1 (T2 in the formula). That is, a phenyl group with a deuterium content of 20% can be represented by the following structural formula.

[0029] [ka]

[0030] In one embodiment of the present application, a "phenyl group having a deuterium content of 0%" can mean a phenyl group that does not contain a deuterium atom, that is, a phenyl group that has 5 hydrogen atoms.

[0031] In this specification, the halogen may be fluorine, chlorine, bromine or iodine.

[0032] In this specification, the alkyl group includes a straight or branched chain having 1 to 60 carbon atoms, and may be further substituted with other substituents. The number of carbon atoms in 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, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a 1-methylbutyl group, a 1-ethylbutyl group, a pentyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a hexyl group, an n-hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a 3,3-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group, a methyl group, an ethyl group, a propyl ... Examples of alkyl groups include, but are not limited to, cyclohexyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, and 5-methylhexyl.

[0033] In this specification, the alkenyl group includes a straight or branched chain having 2 to 60 carbon atoms and may be further substituted with other substituents. The number of carbon atoms in the alkenyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20. Specific examples include, but are not limited to, a vinyl group, a 1-propenyl group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 3-methyl-1-butenyl group, a 1,3-butadienyl group, an allyl group, a 1-phenylvinyl-1-yl group, a 2-phenylvinyl-1-yl group, a 2,2-diphenylvinyl-1-yl group, a 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl group, a 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, a stilbenyl group, and a styrenyl group.

[0034] In this specification, the alkynyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted with other substituents. The alkynyl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 2 to 20 carbon atoms.

[0035] In this specification, the alkoxy group may be a straight chain, branched chain, or cyclic chain. The number of carbon atoms in the alkoxy group is not particularly limited, but preferably is 1 to 20. Specific examples of the alkoxy group include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, and p-methylbenzyloxy.

[0036] In this specification, the cycloalkyl group includes a monocyclic or polycyclic group having 3 to 60 carbon atoms and may be further substituted with other substituents. Here, polycyclic means a group in which a cycloalkyl group is directly bonded to or condensed with another cyclic group. Here, the other cyclic group may be a cycloalkyl group, but may also be other types of cyclic groups, such as a heterocycloalkyl group, an aryl group, or a heteroaryl group. The number of carbon atoms in the cycloalkyl group may be 3 to 60, specifically 3 to 40, more specifically 5 to 20. Specific examples include, but are not limited to, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 3-methylcyclopentyl group, a 2,3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 2,3-dimethylcyclohexyl group, a 3,4,5-trimethylcyclohexyl group, a 4-tert-butylcyclohexyl group, a cycloheptyl group, and a cyclooctyl group.

[0037] In this specification, the heterocycloalkyl group contains O, S, Se, N, or Si as a heteroatom, includes a monocyclic or polycyclic group having 2 to 60 carbon atoms, and may be further substituted with other substituents. Here, the term "polycyclic group" refers to a group in which the heterocycloalkyl group is directly bonded to or condensed with another cyclic group. Here, the other cyclic group may be a heterocycloalkyl group, but may also be other types of cyclic groups, such as a cycloalkyl group, an aryl group, or a heteroaryl group. The number of carbon atoms in the heterocycloalkyl group may be 2 to 60, specifically 2 to 40, more specifically 3 to 20.

[0038] In this specification, the aryl group includes a monocyclic or polycyclic ring having 6 to 60 carbon atoms and may be further substituted with other substituents. Here, polycyclic refers to a group in which an aryl group is directly bonded to or fused with another cyclic group. Here, the other cyclic group may be an aryl group, but it may also be other types of cyclic groups, such as a cycloalkyl group, a heterocycloalkyl group, or a heteroaryl group. The number of carbon atoms in the aryl group may be 6 to 60, specifically 6 to 40, and more specifically 6 to 25. Specific examples of the aryl group include a phenyl group, a biphenyl group, a triphenyl group, a naphthyl group, an anthryl group, a chrysenyl group, a phenanthrenyl group, a perylenyl group, a fluoranthenyl group, a triphenylenyl group, a phenalenyl group, a pyrenyl group, a tetracenyl group, a pentacenyl group, an indenyl group, an acenaphthylenyl group, a 2,3-dihydro-1H-indenyl group, and fused cyclic groups thereof, but are not limited to these.

[0039] As used herein, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

[0040] When the fluorenyl group is substituted, it may have the following structural formula, but is not limited to these.

[0041] [ka]

[0042] In this specification, the heteroaryl group contains S, O, Se, N, or Si as a heteroatom, includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted with other substituents. Here, the polycyclic ring refers to a group in which the heteroaryl group is directly bonded to or condensed with another cyclic group. Here, the other cyclic group may be a heteroaryl group, but may also be other types of cyclic groups, such as a cycloalkyl group, a heterocycloalkyl group, or an aryl group. The number of carbon atoms in the heteroaryl group may be 2 to 60, specifically 2 to 40, more specifically 3 to 25.Specific examples of the heteroaryl group include a pyridyl group, a pyrrolyl group, a pyrimidyl group, a pyridazinyl group, a furanyl group, a thiophene group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, a furazanyl group, an oxadiazolyl group, a thiadiazolyl group, a dithiazolyl group, a tetrazolyl group, a pyranyl group, a thiopyranyl group, a diazinyl group, an oxazinyl group, a thiazinyl group, a dioxinyl group, a triazinyl group, a tetrazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, an isoquinazolinyl group, a quinozolyl group, a naphthyridyl group, an acridinyl group, a phenanthridinyl group, an imidazopyridinyl group, a diazanaphthalenyl group, a triazaindene group, an indolyl group, an indolizinyl group, a benzothiazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiophene group, a benzofuran group, a dibenzothiophene group, a dibenzofuran group, a carbazolyl group, a benzo Carbazolyl group, dibenzocarbazolyl group, phenazinyl group, dibenzosilole group, spirobi(dibenzosilole), dihydrophenazinyl group, phenoxazinyl group, phenanthridyl group, imidazopyridinyl group, thienyl group, indolo[2,3-a]carbazolyl group, indolo[2,3-b]carbazolyl group, indolinyl group, 10,11-dihydro-dibenzo[b,f]azepine group, 9,10-dihydroacridinyl group, phenanthrazinyl group, phenothiazolyl group, Examples of such an alkyl group include, but are not limited to, thiazinyl, phthalazinyl, naphthyridinyl, phenanthrolinyl, benzo[c][1,2,5]thiadiazolyl, 5,10-dihydrodibenzo[b,e][1,4]azasilinyl, pyrazolo[1,5-c]quinazolinyl, pyrido[1,2-b]indazolyl, pyrido[1,2-a]imidazo[1,2-e]indolinyl, and 5,11-dihydroindeno[1,2-b]carbazolyl.

[0043] In this specification, the amine group may be selected from the group consisting of a monoalkylamine group, a monoarylamine group, a monoheteroarylamine group, —NH2, a dialkylamine group, a diarylamine group, a diheteroarylamine group, an alkylarylamine group, an alkylheteroarylamine group, and an arylheteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, a dibiphenylamine group, an anthracenylamine group, a 9-methylanthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a triphenylamine group, a biphenylnaphthylamine group, a phenylbiphenylamine group, a biphenylfluorenylamine group, a phenyltriphenylenylamine group, and a biphenyltriphenylenylamine group, but are not limited to these.

[0044] In this specification, an arylene group refers to an aryl group having two bonding positions, i.e., a divalent group. The above-mentioned explanation of the aryl group is applicable to these groups, except that they are both divalent groups. Furthermore, a heteroarylene group refers to a heteroaryl group having two bonding positions, i.e., a divalent group. The above-mentioned explanation of the heteroaryl group is applicable to these groups, except that they are both divalent groups.

[0045] In this specification, the phosphine oxide group is represented by -P(=O)R101R102, where R101 and R102 may be the same or different and each independently represent at least one substituent selected from the group consisting of hydrogen, deuterium, a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a cycloalkyl group, an aryl group, and a heterocyclic group. Specific examples of the phosphine oxide group include, but are not limited to, diphenylphosphine oxide and dinaphthylphosphine oxide.

[0046] In this specification, a silyl group refers to a substituent containing Si and having the Si atom directly bonded as a radical, and is represented by -SiR104R105R106, where R104 to R106 may be the same or different and each independently represent at least one of hydrogen, deuterium, a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a cycloalkyl group, an aryl group, and a heterocyclic group. Specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.

[0047] As used herein, the term "adjacent" refers to a substituent substituted on an atom directly bonded to the atom on which the substituent is substituted, a substituent sterically closest to the substituent, or another substituent substituted on the atom on which the substituent is substituted. For example, two substituents substituted at ortho positions on a benzene ring and two substituents substituted on the same carbon atom on an aliphatic ring can be interpreted as groups "adjacent" to each other.

[0048] The aliphatic or aromatic hydrocarbon ring or heterocycle that can be formed by adjacent groups has the same structures as those exemplified above for the cycloalkyl group, cycloheteroalkyl group, aryl group, and heteroaryl group, except that it is not a monovalent group.

[0049] As used herein, the term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position of the substitution is not limited as long as it is a position at which a hydrogen atom is substituted, i.e., a position at which a substituent can be substituted, and when two or more substituents are substituted, the two or more substituents may be the same or different from each other.

[0050] In this specification, the term "substituted or unsubstituted" means being substituted or unsubstituted with one or more substituents selected from the group consisting of C1 to C60 linear or branched alkyl; C2 to C60 linear or branched alkenyl; C2 to C60 linear or branched alkynyl; C3 to C60 monocyclic or polycyclic cycloalkyl; C2 to C60 monocyclic or polycyclic heterocycloalkyl; C6 to C60 monocyclic or polycyclic aryl; C2 to C60 monocyclic or polycyclic heteroaryl; -SiRR'R''; -P(=O)RR'; C1 to C20 alkylamine; C6 to C60 monocyclic or polycyclic arylamine; and C2 to C60 monocyclic or polycyclic heteroarylamine, or being substituted or unsubstituted with a substituent in which two or more substituents selected from the above-mentioned exemplary substituents are linked together, The R, R', and R'' may be the same or different, and each independently represent a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0051] In one embodiment of the present application, there is provided a compound represented by Chemical Formula 1.

[0052] In particular, in Formula 1, N-Het substituted on one benzene ring of dibenzofuran is a substituent with electron transport properties, and further characterized as a trisubstituted compound having Ar1 and Ar2 substituents at the 4-position of each benzene ring of dibenzofuran. Blocking the 4-position of the benzene ring, which is an electronically weak position of dibenzofuran, with the Ar1 and Ar2 substituents enhances thermal stability, resulting in a particularly improved lifetime of organic light-emitting devices containing the compound.

[0053] In one embodiment of the present application, the deuterium content of the heterocyclic compound represented by Chemical Formula 1 may be 0% or more and 100% or less, preferably 20% or more and 100% or less, and more preferably 40% or more and 100% or less.

[0054] In one embodiment of the present application, the deuterium content of the heterocyclic compound represented by Chemical Formula 1 may be 0% or 100%.

[0055] In one embodiment of the present application, the above-mentioned Chemical Formula 1 may be represented by the following Chemical Formula 2 or 3.

[0056] [ka] [ka] In the above Chemical Formulas 2 and 3, The definitions of X, R3 to R5, N-Het, Ar1, Ar2, L1 to L3, a, b, m, n, p, and q are the same as those in Chemical Formula 1 above.

[0057] In one embodiment of the present application, the chemical formula 1 can be represented by any one of the following chemical formulas 4 to 10.

[0058] [ka] [ka] [ka] [ka] [ka] [ka] [ka] In the above chemical formulas 4 to 10, The definitions of X, N-Het, R3 to R5, L1 to L3, m, n, p, q, a, and b are the same as those in Chemical Formula 1. X1 and X2 are the same or different and each independently represent O; S; or NR31; Ar3 and Ar4 are the same or different and each independently represent a substituted or unsubstituted C6 to C60 aryl group; R11 to R18 and R21 to R28 are the same or different and each independently represent a hydrogen atom; a deuterium atom; a halogen atom; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; -SiRR'R'' and -NRR'; or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 aliphatic or aromatic heterocycle; wherein R31, R, R', and R'' are the same or different and each independently represent a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; c is an integer of 0 to 3, and when c is 2 or more, the substituents in the parentheses are the same or different.

[0059] In one embodiment of the present application, L1 to L3 are the same or different and may each independently represent a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group.

[0060] In yet another embodiment, L1 to L3 are the same or different and may each independently be a direct bond; a substituted or unsubstituted C6 to C40 arylene group; or a substituted or unsubstituted C2 to C40 heteroarylene group.

[0061] In yet another embodiment, L1 to L3 may be the same or different and each independently represent a direct bond; or a substituted or unsubstituted C6 to C40 monocyclic or polycyclic arylene group.

[0062] In yet another embodiment, L1 to L3 may be the same or different and each independently represent a direct bond; or a substituted or unsubstituted C6 to C20 monocyclic arylene group.

[0063] In another embodiment, L1 to L3 may be the same or different and each independently represent a direct bond; or a C6 to C20 monocyclic arylene group.

[0064] In another embodiment, L1 to L3 may be the same or different and each independently represent a direct bond or a phenylene group.

[0065] In one embodiment of the present application, the deuterium content of L1 to L3 may be 0% or more and 100% or less, preferably 20% or more and 100% or less, and more preferably 40% or more and 100% or less.

[0066] In one embodiment of the present application, the deuterium content of L1 to L3 may be 0% or 100%.

[0067] In one embodiment of the present application, R3 to R5 are the same or different and each independently represent a hydrogen atom; a deuterium atom; a halogen atom; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; -SiRR'R'' and -NRR'; or two or more adjacent groups may be bonded to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 aliphatic or aromatic heterocycle.

[0068] In yet another embodiment, R3 to R5 are the same or different and each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C6 to C40 aryl group; and a substituted or unsubstituted C2 to C40 heteroaryl group, or two or more adjacent groups may be bonded to each other to form a substituted or unsubstituted C6 to C40 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C40 aromatic heterocycle.

[0069] In yet another embodiment, R3 to R5 may be hydrogen or deuterium.

[0070] In one embodiment of the present application, X may be O.

[0071] In one embodiment of the present application, X may be S.

[0072] In one embodiment of the present application, N-Het may be a substituted or unsubstituted monocyclic or polycyclic heterocyclic group containing one or more N's.

[0073] In yet another embodiment, N-Het may be a substituted or unsubstituted monocyclic or polycyclic C2 to C60 heterocyclic group containing 1 to 3 N atoms.

[0074] In yet another embodiment, N-Het may be a substituted or unsubstituted monocyclic or polycyclic C2 to C40 heterocyclic group containing 1 to 3 N atoms.

[0075] In yet another embodiment, N-Het is unsubstituted or substituted with one or more substituents selected from the group consisting of C6 to C40 aryl groups and C2 to C40 heteroaryl groups, and may be a monocyclic or polycyclic C2 to C40 heterocyclic group containing 1 to 3 N.

[0076] In yet another embodiment, N-Het can be a substituted or unsubstituted triazine group; a substituted or unsubstituted pyrimidine group; a substituted or unsubstituted pyridine group; a substituted or unsubstituted quinoline group; a substituted or unsubstituted 1,10-phenanthroline group; a substituted or unsubstituted 1,7-phenanthroline group; a substituted or unsubstituted quinazoline group; a substituted or unsubstituted pyrido[3,2-d]pyrimidine; or a substituted or unsubstituted benzimidazole group.

[0077] In yet another embodiment, N-Het may be a triazine group substituted or unsubstituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, and a naphthyl group; a pyrimidine group substituted or unsubstituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, a quinoline group, and a naphthyl group; a pyridine group substituted or unsubstituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, a quinoline group, and a naphthyl group; a quinoline group substituted or unsubstituted with a phenyl group; a 1,10-phenanthroline group substituted or unsubstituted with a phenyl group; a 1,7-phenanthroline group substituted or unsubstituted with a phenyl group; a quinazoline group substituted or unsubstituted with a phenyl group or a biphenyl group; or a benzimidazole group substituted or unsubstituted with a phenyl group or a biphenyl group.

[0078] In one embodiment of the present application, the 1,10-phenanthroline group may be represented by the following Chemical Formula 1-1, the 1,7-phenanthroline group may be represented by the following Chemical Formula 1-2, and the pyrido[3,2-d]pyrimidine may be represented by the following Chemical Formula 1-3.

[0079] [ka] [ka] [ka]

[0080] In one embodiment of the present application, the deuterium content of the N-Het may be 0% or more and 100% or less, preferably 20% or more and 100% or less, and more preferably 40% or more and 100% or less.

[0081] In one embodiment of the present application, the deuterium content of the N-Het may be 0% or 100%.

[0082] In one embodiment of the present application, Ar1 and Ar2 are the same or different and may each independently be a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; or -SiRR'R''.

[0083] In yet another embodiment, Ar1 and Ar2 may be the same or different and each independently represent a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0084] In yet another embodiment, Ar1 and Ar2 may be the same or different and each independently may be a C6 to C60 aryl group; or a C2 to C60 heteroaryl group substituted or unsubstituted with one or more substituents selected from the group consisting of a C6 to C60 aryl group and a C1 to C20 alkyl group.

[0085] In yet another embodiment, Ar1 and Ar2 may be the same or different and each independently may be a C6 to C40 aryl group; or a C2 to C40 heteroaryl group substituted or unsubstituted with one or more substituents selected from the group consisting of a C6 to C40 aryl group and a C1 to C10 alkyl group.

[0086] In one embodiment of the present application, the deuterium content of Ar1 and Ar2 may be 0% or more and 100% or less, preferably 20% or more and 100% or less, and more preferably 40% or more and 100% or less.

[0087] In one embodiment of the present application, the deuterium content of Ar1 and Ar2 may be 0% or 100%.

[0088] In one embodiment of the present application, X1 and X2 are the same or different from each other and may each independently be O; S; or NR31.

[0089] In one embodiment of the present application, Ar3 and Ar4 may be the same or different and each independently may be a substituted or unsubstituted C6 to C60 aryl group.

[0090] In yet another embodiment, Ar3 and Ar4 may be a substituted or unsubstituted C6 to C40 monocyclic or polycyclic aryl group.

[0091] In another embodiment, Ar3 and Ar4 may be a C6 to C40 monocyclic or polycyclic aryl group.

[0092] In another embodiment, Ar3 and Ar4 may be a C6 to C40 monocyclic aryl group.

[0093] In another embodiment, Ar3 and Ar4 may be a C6 to C40 polycyclic aryl group.

[0094] In yet another embodiment, Ar3 and Ar4 may be a phenyl group; a biphenyl group; or a naphthyl group.

[0095] In one embodiment of the present application, the deuterium content of Ar3 and Ar4 may be 0% or more and 100% or less, preferably 20% or more and 100% or less, and more preferably 40% or more and 100% or less.

[0096] In one embodiment of the present application, the deuterium content of Ar3 and Ar4 may be 0% or 100%.

[0097] In one embodiment of the present application, R11 to R18 and R21 to R28 are the same or different and each independently represent a hydrogen atom; a deuterium atom; a halogen atom; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; -SiRR'R'' and -NRR'; or two or more adjacent groups may be bonded to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 aliphatic or aromatic heterocycle.

[0098] In yet another embodiment, R11 to R18 and R21 to R28 are the same or different and are each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C6 to C60 aryl group; and a substituted or unsubstituted C2 to C60 heteroaryl group, or two or more adjacent groups may be bonded to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 aliphatic or aromatic heterocycle.

[0099] In yet another embodiment, R11 to R18 and R21 to R28 are the same or different and are each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C6 to C40 aryl group; and a substituted or unsubstituted C2 to C40 heteroaryl group, or two or more adjacent groups may be bonded to each other to form a substituted or unsubstituted C6 to C40 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C40 aromatic heterocycle.

[0100] In yet another embodiment, R11 to R18 and R21 to R28 are the same or different and each independently selected from the group consisting of hydrogen; deuterium; a C6 to C40 aryl group; and a C2 to C40 heteroaryl group substituted or unsubstituted with a C6 to C40 aryl group, or two or more adjacent groups may be bonded to each other to form a C6 to C40 aromatic hydrocarbon ring substituted or unsubstituted with a C1 to C20 alkyl group or a C2 to C40 aromatic heterocycle substituted or unsubstituted with a C6 to C40 aryl group.

[0101] In yet another embodiment, R11 to R18 and R21 to R28 are the same or different and each independently represent hydrogen; deuterium; a phenyl group; a biphenyl group; or a carbazole group unsubstituted or substituted with a phenyl group, or two or more adjacent groups may be bonded to each other to form a benzothiophene ring; a benzofuran ring; an indole ring unsubstituted or substituted with a phenyl group; or an indene ring unsubstituted or substituted with a methyl group.

[0102] In one embodiment of the present application, R, R', and R'' are the same or different and may each independently be a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0103] In another embodiment, R, R', and R'' may be the same or different and may each independently be a substituted or unsubstituted C6 to C60 aryl group.

[0104] In another embodiment, R, R', and R'' may be the same or different and each independently represent a substituted or unsubstituted C6 to C60 monocyclic or polycyclic aryl group.

[0105] In another embodiment, R, R', and R'' may be the same or different and each independently represent a substituted or unsubstituted C6 to C40 monocyclic aryl group.

[0106] In another embodiment, R, R', and R'' may be the same or different and each independently represent a C6 to C20 monocyclic aryl group.

[0107] In yet another embodiment, R, R', and R'' may be phenyl groups.

[0108] In one embodiment of the present application, R31 has the same definition as R above.

[0109] According to one embodiment of the present application, the above-mentioned Chemical Formula 1 may be represented by any of the following compounds, but is not limited thereto:

[0110] [ka] TIFF0007774309000019.tif196161 TIFF0007774309000020.tif191161 TIFF0007774309000021.tif197161 TIFF0007774309000022.tif185161 TIFF0007774309000023.tif192161 TIFF0007774309000024.tif188161 TIFF0007774309000025.tif183161 TIFF0007774309000026.tif189161 TIFF0007774309000027.tif179161 TIFF0007774309000028.tif189161 TIFF0007774309000029.tif194161 TIFF0007774309000030.tif165161

[0111] Furthermore, by introducing various substituents into the structure of Chemical Formula 1, it is possible to synthesize compounds having properties specific to the introduced substituents. For example, by introducing into the core structure substituents that are primarily used in hole injection layer materials, hole transport materials, light emitting layer materials, electron transport layer materials, and charge generation layer materials used in the manufacture of organic light emitting devices, it is possible to synthesize materials that satisfy the requirements for each organic layer.

[0112] In addition, by introducing various substituents into the structure of Chemical Formula 1, it is possible to finely adjust the energy band gap, while improving the properties at the interface between organic materials, thereby diversifying the applications of the material.

[0113] On the other hand, the compound has a high glass transition temperature (Tg) and excellent thermal stability, which is an important factor in providing the device with operational stability.

[0114] In addition, in one embodiment of the present application, there is provided an organic light-emitting device comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers contains a heterocyclic compound represented by Chemical Formula 1.

[0115] In one embodiment of the present application, the first electrode may be an anode and the second electrode may be a cathode.

[0116] In yet another embodiment, the first electrode may be a cathode and the second electrode may be an anode.

[0117] In one embodiment of the present application, the organic light-emitting device may be a blue organic light-emitting device, and the heterocyclic compound of Chemical Formula 1 may be used as a material for the blue organic light-emitting device.

[0118] In one embodiment of the present application, the organic light-emitting device may be a green organic light-emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material for the green organic light-emitting device.

[0119] In one embodiment of the present application, the organic light-emitting device may be a red organic light-emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material for the red organic light-emitting device.

[0120] In one embodiment of the present application, the organic light emitting device may be a blue organic light emitting device, and the heterocyclic compound of Chemical Formula 1 may be used as an emission layer material of the blue organic light emitting device.

[0121] In one embodiment of the present application, the organic light-emitting device may be a green organic light-emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material for the light-emitting layer of the green organic light-emitting device.

[0122] In one embodiment of the present application, the organic light-emitting device may be a red organic light-emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material for the light-emitting layer of the red organic light-emitting device.

[0123] The specific details of the heterocyclic compound represented by Chemical Formula 1 are as described above.

[0124] The organic light-emitting device of the present invention can be manufactured by a conventional method and materials for manufacturing an organic light-emitting device, except that one or more organic layers are formed using the heterocyclic compound described above.

[0125] The heterocyclic compound may be formed into an organic layer by a solution coating method as well as a vacuum deposition method during fabrication of an organic light emitting device, including, but not limited to, spin coating, dip coating, inkjet printing, screen printing, spraying, and roll coating.

[0126] The organic material layer of the organic light-emitting device of the present invention may have a single-layer structure, or may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, an emitting layer, an electron transport layer, an electron injection layer, etc. as organic material layers. However, the structure of the organic light-emitting device is not limited thereto and may include a fewer number of organic material layers.

[0127] In the organic light emitting device of the present invention, the organic material layer may include a light emitting layer, and the light emitting layer may include a heterocyclic compound of Chemical Formula 1.

[0128] In the organic light emitting device of the present invention, the organic material layer may include a light emitting layer, and the light emitting layer may include a heterocyclic compound of Chemical Formula 1 as a light emitting layer host.

[0129] In an organic light-emitting device according to an embodiment of the present application, the organic material layer containing the heterocyclic compound represented by Chemical Formula 1 further contains a heterocyclic compound represented by Chemical Formula A below:

[0130] [ka] In the above chemical formula A, Rc and Rd are the same or different and each independently selected from the group consisting of hydrogen, deuterium, a halogen group, -CN, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C60 cycloalkyl group, a substituted or unsubstituted C2-C60 heterocycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C2-C60 heteroaryl group, -SiR201R202R203; -P(=O)R201R202; and -NR201R202, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6-C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2-C60 heterocycle; Ra and Rb are the same or different and each independently represent a substituted or unsubstituted C6 to C60 aryl group; -SiR201R202R203; -P(=O)R201R202; or a substituted or unsubstituted C2 to C60 heteroaryl group; R201, R202, and R203 are the same or different and each independently represent hydrogen; deuterium; -CN; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group; r and s are integers from 0 to 7, When r and s are 2 or more, the substituents in parentheses may be the same or different.

[0131] When the heterocyclic compound of Formula 1 and the heterocyclic compound of Formula A are contained in the organic material layer of an organic light emitting device, better efficiency and lifespan effects are exhibited. From this result, it can be predicted that an exciplex phenomenon occurs when the two compounds are contained simultaneously.

[0132] The exciplex phenomenon is a phenomenon in which electron exchange between two molecules releases energy equivalent to the HOMO level of the donor (p-host) and the LUMO level of the acceptor (n-host). When the exciplex phenomenon occurs between the two molecules, reverse intersystem crossing (RISC) occurs, which can increase the internal quantum efficiency of fluorescence to 100%. When a donor (p-host) with good hole transporting ability and an acceptor (n-host) with good electron transporting ability are used as the host in the emitting layer, holes are injected into the p-host and electrons are injected into the n-host, which can reduce the driving voltage and thereby improve the lifetime.

[0133] In one embodiment of the present application, the chemical formula A may be represented by the following chemical formula A-1:

[0134] [ka] In the above chemical formula A-1, Rc, Rd, r, and s are the same as those in Chemical Formula A. Ra1 and Rb1 are the same or different and each independently represent a substituted or unsubstituted C6 to C60 aryl group; SiR201R202R203; or -P(=O)R201R202; R201, R202 and R203 are the same as defined in Chemical Formula A above.

[0135] In one embodiment of the present application, Rc and Rd in the above formula A may be hydrogen.

[0136] In one embodiment of the present application, Ra1 and Rb1 in the above chemical formula A-1 may be the same or different, and may each independently be a substituted or unsubstituted C6 to C60 aryl group.

[0137] In another embodiment, Ra1 and Rb1 in the above chemical formula A-1 may be the same or different and may each independently be a substituted or unsubstituted C6 to C40 aryl group.

[0138] In another embodiment, Ra1 and Rb1 in the chemical formula A-1 may be the same or different and may each independently represent a C6 to C40 aryl group substituted or unsubstituted with one or more substituents selected from the group consisting of a C1 to C40 alkyl group, a C6 to C40 aryl group, -CN, and -SiR201R202R203.

[0139] In another embodiment, Ra1 and Rb1 in the chemical formula A-1 may be the same or different and may each independently represent a phenyl group, a phenyl group substituted or unsubstituted with -CN or -SiR201R202R203; a biphenyl group substituted or unsubstituted with a phenyl group; a naphthyl group; a fluorene group substituted or unsubstituted with a methyl group or a phenyl group; a spirobifluorene group; or a triphenylene group.

[0140] In one embodiment of the present application, R201, R202, and R203 in the above chemical formula A-1 may be a phenyl group.

[0141] In one embodiment of the present application, the definitions of R201, R202 and R203 may be the same as the definitions of R, R' and R'' above.

[0142] In one embodiment of the present application, the heterocyclic compound of formula A can be represented by any of the following compounds:

[0143] [ka] TIFF0007774309000034.tif220161 TIFF0007774309000035.tif211161 TIFF0007774309000036.tif218161

[0144] Another embodiment of the present application provides a composition for an organic layer of an organic light-emitting device, comprising a heterocyclic compound represented by Chemical Formula 1 and a heterocyclic compound represented by Chemical Formula A.

[0145] The specific details of the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula A are as described above.

[0146] The weight ratio of the heterocyclic compound represented by Chemical Formula 1 to the heterocyclic compound represented by Chemical Formula A in the composition may be, but is not limited to, 1:10 to 10:1, 1:8 to 8:1, 1:5 to 5:1, or 1:2 to 2:1.

[0147] The composition can be used to form an organic material of an organic light-emitting device, and is particularly preferably used to form a host for the light-emitting layer.

[0148] In one embodiment of the present application, the organic layer includes the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula A, and can be used together with a phosphorescent dopant.

[0149] In one embodiment of the present application, the organic layer includes the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula A, and can be used together with an iridium-based dopant.

[0150] The phosphorescent dopant material may be any material known in the art.

[0151] For example, phosphorescent dopant materials represented by LL'MX', LL'L''M, LMX'X'', L2MX', and L3M can be used, but these examples do not limit the scope of the present invention.

[0152] Here, L, L', L'', X' and X'' are different bidentate ligands, and M is a metal that forms an octahedral complex.

[0153] M may be iridium, platinum, osmium, or the like.

[0154] L is an anionic bidentate ligand that coordinates to M in the iridium-based dopant through the Sp2 carbon and heteroatom, and X can function as an electron or hole trap. Non-limiting examples of L include 2-(1-naphthyl)benzoxazole, (2-phenylbenzoxazole), (2-phenylbenzothiazole), (2-phenylbenzothiazole), (7,8-benzoquinoline), (thiophene-based pyridine), phenylpyridine, benzothiophene-based pyridine, 3-methoxy-2-phenylpyridine, thiophene-based pyridine, and tolylpyridine. Non-limiting examples of X' and X'' include acetylacetonate (acac), hexafluoroacetylacetonate, salicylidene, picolinate, and 8-hydroxyquinolinate.

[0155] More specific examples are given below, but the present invention is not limited to these examples.

[0156] [ka]

[0157] In one embodiment of the present application, the iridium-based dopant may be Ir(ppy)3 as a green phosphorescent dopant.

[0158] In one embodiment of the present application, the content of the dopant may be 1% to 15%, preferably 3% to 10%, and more preferably 5% to 10%, based on the entire light-emitting layer.

[0159] The content may refer to a weight ratio.

[0160] In the organic light-emitting device of the present invention, the organic material layer may include an electron injection layer or an electron transport layer, and the electron injection layer or the electron transport layer may include the heterocyclic compound.

[0161] In another organic light emitting device, the organic material layer may include an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer may include the heterocyclic compound.

[0162] In another organic light emitting device, the organic material layer may include an electron transport layer, an emitting layer, or a hole blocking layer, and the electron transport layer, the emitting layer, or the hole blocking layer may include the heterocyclic compound.

[0163] The organic light-emitting device of the present invention may further include one or more layers selected from the group consisting of a light-emitting layer, a hole-injection layer, a hole-transport layer, an electron-injection layer, an electron-transport layer, an electron-blocking layer, and a hole-blocking layer.

[0164] 1 to 3 illustrate examples of the stacking order of electrodes and organic layers of an organic light-emitting device according to one embodiment of the present application. However, these drawings are not intended to limit the scope of the present application, and structures of organic light-emitting devices known in the art are also applicable to the present application.

[0165] 1 shows an organic light emitting device in which an anode 200, an organic material layer 300, and a cathode 400 are sequentially stacked on a substrate 100. However, the present invention is not limited to this structure, and an organic light emitting device in which a cathode, an organic material layer, and an anode are sequentially stacked on a substrate, as shown in FIG.

[0166] 3 illustrates an example in which the organic material layer is multi-layered. The organic light emitting device of FIG. 3 includes a hole injection layer 301, a hole transport layer 302, an 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 to such a stacked structure. If necessary, the remaining layers except for the emitting layer may be omitted, and other necessary functional layers may be further added.

[0167] In one embodiment of the present application, there is provided a method for manufacturing an organic light-emitting device, comprising the steps of: preparing a substrate; forming a first electrode on the substrate; forming one or more organic material layers on the first electrode; and forming a second electrode on the organic material layers, wherein the step of forming the organic material layers includes forming one or more organic material layers using a composition for an organic material layer according to one embodiment of the present application.

[0168] In one embodiment of the present application, there is provided a method for manufacturing an organic light-emitting device, wherein the step of forming the organic material layer comprises pre-mixing the heterocyclic compound of Chemical Formula 1 and the heterocyclic compound of Chemical Formula A and forming the organic material layer using a thermal vacuum deposition method.

[0169] The term "pre-mixed" means that the heterocyclic compound of Formula 1 and the heterocyclic compound of Formula A are mixed in advance in a single source before being deposited on an organic layer.

[0170] The premixed materials can be described as an organic layer composition according to one embodiment of the present application.

[0171] The organic layer containing Chemical Formula 1 may further contain other materials as needed.

[0172] The organic layer containing both Chemical Formula 1 and Chemical Formula A may further contain other materials as needed.

[0173] In an organic light-emitting device according to one embodiment of the present application, materials other than the compound of Chemical Formula 1 or Chemical Formula A 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 substituted with materials known in the art.

[0174] The anode material may be a material with a relatively large work function, such as a transparent conductive oxide, a metal, or a conductive polymer. Specific examples of the anode material include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

[0175] The cathode material may be a material with a relatively low work function, such as a metal, a metal oxide, or a conductive polymer. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; and multilayer structure materials such as LiF / Al or LiO2 / Al.

[0176] As the hole injection material, known hole injection materials can be used, for example, phthalocyanine compounds such as copper phthalocyanine disclosed in U.S. Pat. No. 4,356,429 or starburst-type amine derivatives described in the literature [Advanced Material, 6, p. 677 (1994)], such as tris(4-carbazoyl-9-ylphenyl)amine (TCTA), 4,4′,4″-tri[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB), and soluble conductive polymer polyaniline / dodecylbenzenesulfonic acid (Polyaniline / Dodecylbenzenesulfonic Acid). Poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate), polyaniline / Camphor sulfonic acid, or polyaniline / Poly(4-styrenesulfonate), etc. can be used.

[0177] As the hole transport material, pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, etc. can be used, and low molecular weight or high molecular weight materials can also be used.

[0178] Examples of electron transport materials that can be used include 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, and metal complexes of 8-hydroxyquinoline and its derivatives. Not only low molecular weight materials but also high molecular weight materials can be used.

[0179] As the electron injection material, for example, LiF is typically used in the industry, but the present application is not limited thereto.

[0180] The light-emitting material may be a red, green, or blue light-emitting material, 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 as separate sources or may be premixed and deposited as a single source. The light-emitting material may be a fluorescent material or a phosphorescent material. The light-emitting material may be a material that emits light by combining holes and electrons injected from the anode and cathode, respectively, or a material in which both the host material and the dopant material contribute to light emission.

[0181] When a mixture of hosts for the light-emitting materials is used, the mixture may be of the same series or different series. For example, two or more materials selected from either n-type host materials or p-type host materials may be used as the host material for the light-emitting layer.

[0182] The organic light emitting device according to one embodiment of the present application may be a top-emitting, bottom-emitting, or double-sided emitting device depending on the materials used.

[0183] The heterocyclic compound according to one embodiment of the present application can also function in organic electronic devices such as organic solar cells, organic photoreceptors, and organic transistors based on a principle similar to that applied to organic light-emitting devices.

[0184] [Mode for Carrying Out the Invention] Hereinafter, the present specification will be described in more detail through embodiments, which are merely for the purpose of illustrating the present application and are not intended to limit the scope of the present application.

[0185] <Production Example 1> Production of Compound 1(D) [ka]

[0186] Preparation of Compound 1-1 1-chlorodibenzo[b,d]furan (15 g, 0.074 mol) and tetrahydrofuran (THF) (150 mL) were placed in a one-neck round-bottom flask and purged with nitrogen. After the bath temperature was lowered to -78 °C, n-BuLi (6.16 g, 0.096 mol) was slowly added dropwise.

[0187] After the reaction was completed, the temperature of the bath was raised to room temperature, and trimethyl borate (11.53 g, 0.111 mol) was added.

[0188] After the reaction was complete, a mixture of iodobenzene (16.61 g, 0.081 mol), tetrakis(triphenylphosphine)palladium(0) (4.28 g, 0.004 mol), potassium carbonate (20.46 g, 0.148 mol), and 1,4-dioxane / water (150 mL / 30 mL) was refluxed at 120 °C.

[0189] The mixture was extracted with dichloromethane, dried over MgSO4, filtered through silica gel, and concentrated to give compound 1-1 (9.56 g, 46.34%).

[0190] Preparation of Compound 1-2 1-chloro-4-phenyldibenzo[b,d]furan (9.56 g, 0.034 mol) and tetrahydrofuran (95 mL) were placed in a one-neck round-bottom flask (one-neck RBF) and purged with nitrogen. After the bath temperature was lowered to -78 °C, n-BuLi (2.83 g, 0.044 mol) was slowly added dropwise.

[0191] After the reaction was completed, the bath temperature was raised to room temperature, and trimethyl borate (5.30 g, 0.051 mol) was added.

[0192] After the reaction was complete, a mixture of iodobenzene (7.63 g, 0.037 mol), tetrakis(triphenylphosphine)palladium(0) (1.96 g, 0.002 mol), potassium carbonate (9.40 g, 0.068 mol), and 1,4-dioxane / water (95 mL / 19 mL) was refluxed at 120 °C.

[0193] The mixture was extracted with dichloromethane, dried over MgSO4, filtered through silica gel, and concentrated to give compound 1-2 (10.50 g, 87%).

[0194] Preparation of Compounds 1-3 A mixture of 1-chloro-4,6-diphenyldibenzo[b,d]furan (10.50 g, 0.030 mol), bis(pinacolato)diboron (15.24 g, 0.060 mol), Pd2(dba)3 (2.75 g, 0.003 mol), PCy3 (1.68 g, 0.006 mol), potassium acetate (8.83 g, 0.090 mol), and 1,4-dioxane (100 mL) was refluxed in a one-neck round-bottom flask at 140 °C.

[0195] The mixture was extracted with dichloromethane, concentrated, and then filtered through silica gel. After concentration, the mixture was treated with dichloromethane / methanol to give compound 1-3 (9.91 g, 74%).

[0196] Preparation of Compound 1(D) A one-neck round-bottom flask was charged with 2-(4,6-diphenyldibenzo[b,d]furan-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (9.91 g, 0.022 mol), 2-chloro-4,6-diphenyl-1,3,5-triazine (6.48 g, 0.024 mol), tetrakis(triphenylphosphine)palladium(0) (1.27 g, 0.001 mol), potassium carbonate (6.08 g, A mixture of 0.044 mol) and 1,4-dioxane / water (90 mL / 27 mL) was refluxed at 120°C.

[0197] The extract was extracted with dichloromethane, dried over MgSO4, and purified using a column to give compound 1(D) (8.13 g, 67%).

[0198] Target compounds D were synthesized in the same manner as in Production Example 1, except that intermediates A, B, and C in Table 1 below were used.

[0199] [Table 1] TIFF0007774309000040.tif219165 TIFF0007774309000041.tif191165 TIFF0007774309000042.tif79165

[0200] [Production Example 2] Production of Compound 41(E) [ka]

[0201] Preparation of Compound 41-1 1-chlorodibenzo[b,d]furan (15 g, 0.074 mol) and THF (150 mL) were placed in a one-neck round-bottom flask and purged with nitrogen. After the bath temperature was lowered to -78 °C, n-BuLi (6.16 g, 0.096 mol) was slowly added dropwise.

[0202] After the reaction was completed, the temperature of the bath was raised to room temperature, and trimethyl borate (11.53 g, 0.111 mol) was added.

[0203] After the reaction was complete, a mixture of iodobenzene (16.61 g, 0.081 mol), tetrakis(triphenylphosphine)palladium(0) (4.28 g, 0.004 mol), potassium carbonate (20.46 g, 0.148 mol), and 1,4-dioxane / water (150 mL / 30 mL) was refluxed at 120 °C.

[0204] The mixture was extracted with dichloromethane, dried over MgSO4, filtered through silica gel, and concentrated to give compound 41-1 (9.56 g, 46.34%).

[0205] Preparation of compound 41-2 1-chloro-4-phenyldibenzo[b,d]furan (9.56 g, 0.034 mol) and THF (95 mL) were placed in a one-neck round-bottom flask (one-neck RBF) and the atmosphere was replaced with nitrogen. After the bath temperature was lowered to -78 °C, n-BuLi (2.83 g, 0.044 mol) was slowly added dropwise.

[0206] After the reaction was completed, the temperature of the bath was raised to room temperature, and iodine (12.94 g, 0.051 mol) was added.

[0207] When the reaction was complete, distilled water was added. The mixture was extracted with dichloromethane and dried over MgSO. After filtration through silica gel, the mixture was concentrated to give compound 41-2 (10.18 g, 74%).

[0208] Preparation of compound 41-3 A mixture of 1-chloro-6-iodo-4-phenyldibenzo[b,d]furan (10.18 g, 0.025 mol), carbazole (4.60 g, 0.028 mol), tris(dibenzylideneacetone)dipalladium(0) (2.29 g, 0.0025 mol), tri-tert-butylphosphine (10 g, 0.049 mol), sodium tert-butoxide (4.81 g, 0.05 mol), and toluene (100 mL) was placed in a one-neck round-bottom flask and refluxed at 130 °C.

[0209] When the reaction was completed, the solid was removed by filtration, and the filtrate was filtered through silica gel and then concentrated to give compound 41-3 (9.77 g, 88%).

[0210] Preparation of compound 41-4 A mixture of 9-(9-chloro-6-phenyldibenzo[b,d]furan-4-yl)-9H-carbazole (9.77 g, 0.022 mol), bis(pinacolato)diboron (11.17 g, 0.044 mol), Pd(dba) (1.01 g, 0.001 mol), PCy (1.23 g, 0.004 mol), potassium acetate (6.84 g, 0.066 mol), and 1,4-dioxane (90 mL) was refluxed in a one-neck round-bottom flask at 140 °C.

[0211] The mixture was extracted with dichloromethane, concentrated, and then filtered through silica gel. After concentration, the mixture was treated with dichloromethane / methanol to give compound 41-4 (8.36 g, 71%).

[0212] Preparation of Compound 41(E) One neck round bottom flask rbf) with 9-(6-phenyl-9-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-4-yl)-9H-carbazole (8.36 g, 0.016 mol), 2-chloro-4,6-diphenyl-1,3,5-triazine (4.71 g, 0.018 mol), tetrakis(triphenylphosphine)palladium(0) (0.92 g, 0.001 mol), and potassium carbonate. A mixture of 4.42 g (0.032 mol) of methyl carbonate and 1,4-dioxane / water (80 mL / 24 mL) was refluxed at 120°C.

[0213] The mixture was extracted with dichloromethane, dried over MgSO4, filtered through silica gel, and concentrated to give compound 41(E) (6.36 g, 62%).

[0214] Target compounds E were synthesized in the same manner as in Production Example 2, except that intermediates A, B, and C in Table 2 below were used.

[0215] [Table 2] TIFF0007774309000045.tif187165 TIFF0007774309000046.tif220165 TIFF0007774309000047.tif214165

[0216] [Production Example 3] Production of Compound 81(F) [ka]

[0217] Preparation of Compound 81-1 1-chlorodibenzo[b,d]furan (15 g, 0.074 mol) and tetrahydrofuran (THF) (150 mL) were placed in a one-neck round-bottom flask and purged with nitrogen. After the bath temperature was lowered to -78 °C, n-BuLi (6.16 g, 0.096 mol) was slowly added dropwise.

[0218] After the reaction was completed, the temperature of the bath was raised to room temperature, and iodine (28.17 g, 0.11 mol) was added.

[0219] When the reaction was complete, distilled water was added. The mixture was extracted with dichloromethane and dried over MgSO. After filtration through silica gel, the mixture was concentrated to give compound 81-1 (17.26 g, 71%).

[0220] Preparation of Compound 81-2 A mixture of 1-chloro-4-iododibenzo[b,d]furan (17.26 g, 0.053 mol), carbazole (9.75 g, 0.058 mol), tris(dibenzylideneacetone)dipalladium(0) (3.06 g, 0.0027 mol), tri-tert-butylphosphine (17 g, 0.084 mol), sodium tert-butoxide (10.19 g, 0.12 mol), and toluene (170 mL) was placed in a one-neck round-bottom flask and refluxed at 130 °C.

[0221] When the reaction was completed, the solid was removed by filtration, and the filtrate was filtered through silica gel and then concentrated to give compound 81-2 (12.48 g, 64%).

[0222] Preparation of compound 81-3 9-(1-chlorodibenzo[b,d]furan-4-yl)-9H-carbazole (12.48 g, 0.034 mol) and THF (120 mL) were placed in a one-neck round-bottom flask (one-neck rbf) and purged with nitrogen. After the bath temperature was lowered to -78 °C, n-BuLi (2.83 g, 0.044 mol) was slowly added dropwise.

[0223] After the reaction was completed, the temperature of the bath was raised to room temperature, and iodine (12.94 g, 0.051 mol) was added.

[0224] When the reaction was complete, distilled water was added. The mixture was extracted with dichloromethane and dried over MgSO. After filtration through silica gel, the mixture was concentrated to give compound 81-3 (11.58 g, 69%).

[0225] Preparation of compound 81-4 A mixture of 9-(1-chloro-6-iododibenzo[b,d]furan-4-yl)-9H-carbazole (11.58 g, 0.023 mol), carbazole (4.23 g, 0.025 mol), tris(dibenzylideneacetone)dipalladium(0) (1.33 g, 0.0012 mol), tri-tert-butylphosphine (4.42 g, 0.046 mol), and toluene (110 mL) was placed in a one-neck round-bottom flask and refluxed at 130°C.

[0226] When the reaction was completed, the solid was removed by filtration, and the filtrate was filtered through silica gel and then concentrated to give compound 81-4 (7.72 g, 63%).

[0227] Preparation of compound 81-5 A mixture of 9,9'-(1-chlorodibenzo[b,d]furan-4,6-diyl)bis(9H-carbazole) (7.72 g, 0.014 mol), bis(pinacolato)diboron (7.11 g, 0.028 mol), Pd2(dba)3 (0.64 g, 0.0007 mol), PCy3 (0.79 g, 0.0028 mol), potassium acetate (4.12 g, 0.042 mol), and 1,4-dioxane (70 mL) was refluxed in a one-neck round-bottom flask at 140 °C.

[0228] The mixture was extracted with dichloromethane, concentrated, filtered through silica gel, and then treated with dichloromethane / methanol to give compound 81-5 (7.69 g, 88%).

[0229] Preparation of Compound 81(F) In a one-neck round-bottom flask (1 neck rbf), 9,9'-(1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-4,6-diyl)bis(9H-carbazole) (7.69 g, 0. A mixture of 2-chloro-4,6-diphenyl-1,3,5-triazine (3.53 g, 0.013 mol), 2-chloro-4,6-diphenyl-1,3,5-triazine (3.53 g, 0.013 mol), tetrakis(triphenylphosphine)palladium(0) (0.69 g, 0.0006 mol), potassium acetate, and 1,4-dioxane / water (75 mL / 23 mL) was refluxed at 120°C.

[0230] The mixture was extracted with dichloromethane, dried over MgSO4, filtered through silica gel, and concentrated to give compound 81(F) (6.48 g, 74%).

[0231] Target compounds F were synthesized in the same manner as in Production Example 3, except that intermediates A, B, and C in Table 3 below were used.

[0232] [Table 3] TIFF0007774309000050.tif218165

[0233] [Production Example 4] Production of Compound 101(G) [ka]

[0234] Preparation of Compound 101-1 3-chlorodibenzo[b,d]furan (15 g, 0.074 mol) and tetrahydrofuran (150 mL) were placed in a one-neck round-bottom flask (RBF) and purged with nitrogen. After the bath temperature was lowered to -78 °C, n-BuLi (6.16 g, 0.096 mol) was slowly added dropwise.

[0235] After the reaction was completed, the temperature of the bath was raised to room temperature, and trimethyl borate (11.53 g, 0.111 mol) was added.

[0236] After the reaction was complete, a mixture of iodobenzene (16.61 g, 0.081 mol), tetrakis(triphenylphosphine)palladium(0) (4.28 g, 0.004 mol), potassium carbonate (20.46 g, 0.148 mol), and 1,4-dioxane / water (150 mL / 30 mL) was refluxed at 120 °C.

[0237] The mixture was extracted with dichloromethane, dried over MgSO4, filtered through silica gel, and concentrated to give compound 101-1 (8.68 g, 42.10%).

[0238] Preparation of Compound 101-2 3-chloro-4-phenyldibenzo[b,d]furan (8.68 g, 0.031 mol) and THF (85 mL) were placed in a one-neck round-bottom flask (one-neck rbf) and purged with nitrogen. After the bath temperature was lowered to -78 °C, n-BuLi (2.58 g, 0.040 mol) was slowly added dropwise.

[0239] After the reaction was completed, the bath temperature was raised to room temperature, and trimethyl borate (4.83 g, 0.047 mol) was added.

[0240] After the reaction was complete, a mixture of iodobenzene (6.96 g, 0.034 mol), tetrakis(triphenylphosphine)palladium(0) (1.79 g, 0.0016 mol), potassium carbonate (8.57 g, 0.062 mol), and 1,4-dioxane / water (42 mL / 8 mL) was refluxed at 120 °C.

[0241] The mixture was extracted with dichloromethane, dried over MgSO4, filtered through silica gel, and concentrated to give compound 101-2 (5.83 g, 53%).

[0242] Preparation of Compound 101-3 A mixture of 3-chloro-4,6-diphenyldibenzo[b,d]furan (5.83 g, 0.016 mol), bis(pinacolato)diboron (8.13 g, 0.032 mol), Pd2(dba)3 (0.73 g, 0.0008 mol), PCy3 (0.90 g, 0.0032 mol), potassium acetate (3.14 g, 0.032 mol), and 1,4-dioxane (50 mL) was refluxed in a one-neck round-bottom flask at 140 °C.

[0243] The mixture was extracted with dichloromethane, concentrated, and then filtered through silica gel. After concentration, the mixture was treated with dichloromethane / methanol to give compound 101-3 (9.41 g, 68%).

[0244] Preparation of Compound 101(G) A one-neck round-bottom flask was charged with 2-(4,6-diphenyldibenzo[b,d]furan-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (9.41 g, 0.020 mol), 2-chloro-4,6-diphenyl-1,3,5-triazine (5.89 g, 0.022 mol), tetrakis(triphenylphosphine)palladium(0) (1.16 g, 0.001 mol), potassium carbonate (5.53 g, A mixture of 0.040 mol) and 1,4-dioxane / water (90 mL / 27 mL) was refluxed at 120°C.

[0245] Extraction with dichloromethane and drying with MgSO4 were carried out, followed by column purification to obtain compound 101(G) (8.50 g, 77%).

[0246] Target compounds G were synthesized in the same manner as in Production Example 4, except that intermediates A, B, and C in Table 4 below were used.

[0247] [Table 4] TIFF0007774309000053.tif218165 TIFF0007774309000054.tif217165 TIFF0007774309000055.tif110165

[0248] [Production Example 5] Production of Compound 141(H) [ka]

[0249] Preparation of Compound 141-1 3-chlorodibenzo[b,d]furan (15 g, 0.074 mol) and THF (150 mL) were placed in a one-neck round-bottom flask and purged with nitrogen. After the bath temperature was lowered to -78 °C, n-BuLi (6.16 g, 0.096 mol) was slowly added dropwise.

[0250] After the reaction was completed, the temperature of the bath was raised to room temperature, and trimethyl borate (11.53 g, 0.111 mol) was added.

[0251] After the reaction was complete, a mixture of iodobenzene (16.61 g, 0.081 mol), tetrakis(triphenylphosphine)palladium(0) (4.28 g, 0.004 mol), potassium carbonate (20.46 g, 0.148 mol), and 1,4-dioxane / water (150 mL / 30 mL) was refluxed at 120 °C.

[0252] The mixture was extracted with dichloromethane, dried over MgSO4, filtered through silica gel, and concentrated to give compound 141-1 (9.90 g, 48%).

[0253] Preparation of Compound 141-2 3-chloro-4-phenyldibenzo[b,d]furan (9.90 g, 0.036 mol) and THF (95 mL) were placed in a one-neck round-bottom flask (one-neck RBF) and the atmosphere was replaced with nitrogen. After the bath temperature was lowered to -78 °C, n-BuLi (3.00 g, 0.047 mol) was slowly added dropwise.

[0254] After the reaction was completed, the temperature of the bath was raised to room temperature, and then iodine (10.05 g, 0.040 mol) was added.

[0255] When the reaction was complete, distilled water was added. The mixture was extracted with dichloromethane and dried over MgSO. After filtration through silica gel, the mixture was concentrated to give compound 141-2 (12.24 g, 84%).

[0256] Preparation of Compound 141-3 A mixture of 3-chloro-6-iodo-4-phenyldibenzo[b,d]furan (12.24 g, 0.030 mol), carbazole (5.52 g, 0.033 mol), tris(dibenzylideneacetone)dipalladium(0) (1.37 g, 0.0015 mol), tri-tert-butylphosphine (6.07 g, 0.030 mol), sodium tert-butoxide (5.77 g, 0.060 mol), and toluene (120 mL) was placed in a one-neck round-bottom flask and refluxed at 130 °C.

[0257] When the reaction was completed, the solid was removed by filtration, and the filtrate was filtered through silica gel and then concentrated to give compound 141-3 (8.92 g, 67%).

[0258] Preparation of Compound 141-4 A mixture of 9-(7-chloro-6-phenyldibenzo[b,d]furan-4-yl)-9H-carbazole (8.92 g, 0.020 mol), bis(pinacolato)diboron (10.20 g, 0.040 mol), Pd(dba) (1.83 g, 0.002 mol), PCy (1.12 g, 0.004 mol), potassium acetate (5.89 g, 0.06 mol), and 1,4-dioxane (90 mL) was refluxed in a one-neck round-bottom flask at 140 °C.

[0259] The mixture was extracted with dichloromethane, concentrated, and then filtered through silica gel. After concentration, the mixture was treated with dichloromethane / methanol to give compound 141-4 (8.35 g, 78%).

[0260] Preparation of Compound 141(H) In a one-neck round-bottom flask, 8.57 g of 9-(6-phenyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-4-yl)-9H-carbazole was placed. A mixture of 2-chloro-4,6-diphenyl-1,3,5-triazine (4.71 g, 0.018 mol), 2-chloro-4,6-diphenyl-1,3,5-triazine (4.71 g, 0.018 mol), tetrakis(triphenylphosphine)palladium(0) (0.92 g, 0.0008 mol), potassium carbonate (4.42 g, 0.032 mol), and 1,4-dioxane / water (85 mL / 25 mL) was refluxed at 120°C.

[0261] The mixture was extracted with dichloromethane, dried over MgSO4, filtered through silica gel, and concentrated to give compound 141(H) (7.89 g, 77%).

[0262] Each of the target compounds H was synthesized in the same manner as in Production Example 5, except that intermediates A, B, and C in Table 5 below were used.

[0263] [Table 5] TIFF0007774309000058.tif218165 TIFF0007774309000059.tif218165 TIFF0007774309000060.tif218165 TIFF0007774309000061.tif111165

[0264] [Production Example 6] Production of Compound 181(I) [ka]

[0265] Preparation of Compound 181-1 3-chlorodibenzo[b,d]furan (15 g, 0.074 mol) and THF (150 mL) were placed in a one-neck round-bottom flask and purged with nitrogen. After the bath temperature was lowered to -78 °C, n-BuLi (6.16 g, 0.096 mol) was slowly added dropwise.

[0266] After the reaction was completed, the temperature of the bath was raised to room temperature, and iodine (28.17 g, 0.11 mol) was added.

[0267] When the reaction was complete, distilled water was added. The mixture was extracted with dichloromethane and dried over MgSO4. After filtration through silica gel, the mixture was concentrated to give compound 181-1 (16.53 g, 68%).

[0268] Preparation of Compound 181-2 A mixture of 3-chloro-4-iododibenzo[b,d]furan (16.53 g, 0.05 mol), carbazole (9.20 g, 0.055 mol), tris(dibenzylideneacetone)dipalladium(0) (2.89 g, 0.0025 mol), tri-tert-butylphosphine (10.12 g, 0.05 mol), sodium tert-butoxide (9.61 g, 0.10 mol), and toluene (165 mL) was placed in a one-neck round-bottom flask and refluxed at 130 °C.

[0269] When the reaction was completed, the solid was removed by filtration, and the filtrate was filtered through silica gel and then concentrated to give compound 181-2 (9.75 g, 53%).

[0270] Preparation of compound 181-3 9-(3-chlorodibenzo[b,d]furan-4-yl)-9H-carbazole (9.75 g, 0.027 mol) and THF (95 mL) were placed in a one-neck round-bottom flask (one-neck rbf) and flushed with nitrogen. After lowering the bath temperature to -78 °C, n-BuLi (2.25 g, 0.035 mol) was slowly added dropwise.

[0271] After the reaction is completed, the bath temperature is raised to room temperature, and iodine (7.54 g, 0.030 mol) is added.

[0272] When the reaction was complete, distilled water was added. The mixture was extracted with dichloromethane and dried over MgSO. After filtration through silica gel, the mixture was concentrated to give compound 181-3 (7.87 g, 59%).

[0273] Preparation of Compound 181-4 In a one-neck round-bottom flask (1-neck RBF), 9-(3-chloro-6-iododibenzo[b,d]furan-4-yl)-9H-carbazole (7.87 g, 0.016 mol), carbazole (2.94 g, 0.018 mol), and tris(dibenzylideneacetone)dipalladium(0) were added. A mixture of (ideneacetone)dipalladium(0) (1.47 g, 0.0016 mol), tri-tert-butylphosphine (3.24 g, 0.016 mol), sodium tert-butoxide (3.08 g, 0.032 mol), and toluene (75 mL) was refluxed at 130 °C.

[0274] When the reaction was completed, the solid was removed by filtration, and the filtrate was filtered through silica gel and then concentrated to give compound 181-4 (6.82 g, 80%).

[0275] Preparation of Compound 181-5 A mixture of 9,9'-(3-chlorodibenzo[b,d]furan-4,6-diyl)bis(9H-carbazole) (6.82 g, 0.013 mol), bis(pinacolato)diboron (6.60 g, 0.026 mol), Pd(dba) (1.19 g, 0.0013 mol), PCy (0.73 g, 0.0026 mol), potassium acetate (3.59 g, 0.026 mol), and 1,4-dioxane (70 mL) was refluxed in a one-neck round-bottom flask at 140 °C.

[0276] The mixture was extracted with dichloromethane, concentrated, and then filtered through silica gel. After concentration, the mixture was treated with dichloromethane / methanol to give compound 181-5 (5.62 g, 71%).

[0277] Preparation of Compound 181(I) In a one-neck round-bottom flask (1 neck rbf), 9,9'-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-4,6-diyl)bis(9H-carbazole) (5.62 g, 0. A mixture of 2-chloro-4,6-diphenyl-1,3,5-triazine (2.68 g, 0.010 mol), tetrakis(triphenylphosphine)palladium(0) (0.52 g, 0.0005 mol), potassium carbonate (2.49 g, 0.018 mol), and 1,4-dioxane / water (55 mL / 16 mL) was refluxed at 120°C.

[0278] The mixture was extracted with dichloromethane, dried over MgSO4, filtered through silica gel, and concentrated to give compound 181(I) (3.74 g, 57%).

[0279] The target compounds I were each synthesized in the same manner as in Preparation Example 6, except that intermediates A, B, and C in Table 6 below were used.

[0280] [Table 6] TIFF0007774309000064.tif218165 TIFF0007774309000065.tif165165

[0281] [Production Example 7] Production of Compound 2-23(E) [ka]

[0282] Preparation of Compound 2-23[E] 9-([1,1'-biphenyl]-2-yl)-9H,9'H-3,3'-bicarbazole (10 g, 0.021 mol), 4-bromo-1,1':4',1''-terphenyl (7.14 g, 0.023 mol), CuI (4.00 g, 0.021 mol), trans-1,4-diaminocyclohexane (2.40 g, 0.021 mol), and KPO (8.92 g, 0.042 mol) were dissolved in 100 mL of 1,4-oxane in a one-neck round-bottom flask, and the mixture was refluxed at 125 °C for 8 hours. After the reaction was complete, the mixture was extracted with distilled water and DCM at room temperature. The organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex=1:3) and recrystallized from methanol to give compound 2-23[E] (13.17 g, 88%).

[0283] Compound E corresponding to chemical formula A in Table 7 below was synthesized in the same manner as in Preparation Example 7 above, except that intermediates A and B in Table 7 below were used.

[0284] [Table 7]

[0285] Heterocyclic compounds corresponding to Chemical Formula 1 and heterocyclic compounds corresponding to Chemical Formula A other than the compounds described in Preparation Examples 1 to 7 and Tables 1 to 7 were also produced in the same manner as in the above-mentioned Preparation Examples.

[0286] The synthesis confirmation data for the compounds prepared above are as shown in Tables 8 and 9 below.

[0287] [Table 8] TIFF0007774309000069.tif232165 TIFF0007774309000070.tif45165

[0288] [Table 9] TIFF0007774309000072.tif222165 TIFF0007774309000073.tif214165 TIFF0007774309000074.tif229165 TIFF0007774309000075.tif221165 TIFF0007774309000076.tif222165 TIFF0007774309000077.tif222165 TIFF0007774309000078.tif230165 TIFF0007774309000079.tif157165

[0289] <Experimental Example 1> - Fabrication of organic light-emitting device 1) Fabrication of organic light-emitting devices A glass substrate coated with a 1,500 Å thick indium tin oxide (ITO) thin film was ultrasonically cleaned in distilled water. After the distilled water cleaning, it was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UVO in a UV cleaner for 5 minutes. The substrate was then transferred to a plasma cleaner (PT) and plasma treated in a vacuum to remove the ITO work function and residual film, before being transferred to a thermal evaporation system for organic deposition.

[0290] A common layer, a hole injection layer 2-TNATA (4,4'-Tris[2-naphthyl(phenyl)amino]triphenylamine) and a hole transport layer NPB (N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine), were formed on the ITO transparent electrode (anode).

[0291] An emitting layer was formed thereon by thermal vacuum deposition as follows. The emitting layer was formed using the compounds listed in Table 10 below as the host and Ir(ppy)3 (tris(2-phenylpyridine)iridium) as the green phosphorescent dopant, doping the host with Ir(ppy)3 at a weight ratio of 7%. A 400 Å thick layer was then deposited. A 60 Å thick layer of BCP was then deposited as a hole-blocking layer, followed by a 200 Å thick layer of Alq3 as an electron-transporting layer. Finally, a 10 Å thick layer of lithium fluoride (LiF) was deposited on the electron-transporting layer to form an electron-injection layer. An aluminum (Al) cathode was then deposited on the electron-injection layer to a thickness of 1200 Å, completing the fabrication of an organic electroluminescent device.

[0292] On the other hand, all the organic compounds required for manufacturing OLED elements are 10 -6 ~10 -8 It was purified by vacuum sublimation under torr and used for the fabrication of OLEDs.

[0293] 2) Driving voltage and luminous efficiency of organic electroluminescent devices The electroluminescence (EL) characteristics of the organic electroluminescent device fabricated as described above were measured using a Mac Science M7000, and the measurement results were used to measure the reference luminance of 6,000 cd / m using a Mac Science M6000 lifespan measurement device. 2 When T 90 The characteristics of the organic electroluminescent device of the present invention are shown in Table 10.

[0294] [Table 10] TIFF0007774309000081.tif233165 TIFF0007774309000082.tif233165 TIFF0007774309000083.tif232165 TIFF0007774309000084.tif110165

[0295] [ka]

[0296] <Experimental Example 2> - Fabrication of organic light-emitting device A glass substrate coated with a 1,500Å thick ITO film was ultrasonically cleaned with distilled water. After the distilled water cleaning, it was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UVO in a UV cleaner for 5 minutes. The substrate was then transferred to a plasma cleaner (PT) and plasma treated in a vacuum to remove the ITO work function and residual film, before being transferred to a thermal evaporation system for organic deposition.

[0297] A common layer, a hole injection layer made of 2-TNATA (4,4',4''-Tris[2-naphthyl(phenyl)amino]triphenylamine) and a hole transport layer made of NPB (N,N'-Di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine), were formed on the ITO transparent electrode (anode).

[0298] An emitting layer was then formed thereon by thermal vacuum deposition as follows: The emitting layer was formed by premixing a compound represented by Chemical Formula 1 as a host with a compound represented by Chemical Formula A (the emitting layer compound in Table 11) and depositing it to a thickness of 400 Å from a single source. The green phosphorescent dopant, Ir(ppy)3, was deposited at a thickness of 7% of the deposited thickness of the emitting layer. Next, BCP was deposited to a thickness of 60 Å as a hole-blocking layer, and Alq3 was deposited to a thickness of 200 Å as an electron-transporting layer on top of that. Finally, lithium fluoride (LiF) was deposited to a thickness of 10 Å on the electron-transporting layer to form an electron-injecting layer. An aluminum (Al) cathode was then deposited to a thickness of 1,200 Å on the electron-injecting layer to form the cathode, completing the fabrication of an organic electroluminescent device.

[0299] On the other hand, all the organic compounds required for manufacturing OLED elements are 10 -6 ~10 -8 It was purified by vacuum sublimation under torr and used for the fabrication of OLEDs.

[0300] The electroluminescence (EL) characteristics of the organic electroluminescent device fabricated as described above were measured using a Mac Science M7000, and the measurement results were used to measure the reference luminance of 6,000 cd / m using a Mac Science M6000 lifespan measurement device. 2 When T 90 was measured.

[0301] The driving voltage, luminous efficiency, color coordinate (CIE), and lifespan of the organic light emitting device manufactured according to the present invention were measured, and the results are shown in Table 11 below.

[0302] [Table 11]

[0303] As can be seen from Table 10, the heterocyclic compound according to the present application has substituents Ar1 and Ar2 at the 4-position of each benzene ring of dibenzofuran, respectively. It has been confirmed that the heterocyclic compound according to the present application has the characteristic of improving the thermal stability by blocking the electronically weak position of dibenzofuran with the substituent, and particularly improving the lifetime of an organic light-emitting device including the heterocyclic compound.

[0304] Dibenzofuran and dibenzothiophene have oxygen and sulfur atoms at their center, which have higher electronegativity than carbon. Within the molecular structure, oxygen and sulfur atoms tend to attract electrons from adjacent carbons. Therefore, the fourth position of the benzene ring in dibenzofuran and dibenzothiophene is weaker than other positions due to a lack of electrons. The objective of the present invention is to increase lifetime and efficiency by combining an aryl group or heteroaryl group, which can donate electrons to these electron-deficient positions.

[0305] In Table 10, we observed some trends in the experimental results depending on the binding position of the N-Het, the ET unit, in each compound. When the N-Het is bound to the 3-position of the dibenzofuran core, the steric hindrance of the molecule itself is greater than when it is bound to the 1-position of the dibenzofuran core. This results in much higher structural stability when the N-Het is bound to the 1-position of the dibenzofuran core. Furthermore, when the material is evaporated to fabricate a device, the stability of the material's packing structure is also higher. For these reasons, when the N-Het is bound to the 1-position of the dibenzofuran, the lifetime and efficiency tend to be better. However, the driving voltage was found to be at a similar level.

[0306] Specifically, in Table 10, specific compounds 1 to 20 and 101 to 120 in which aryl groups are bonded as substituents to all of the 4-positions of each benzene ring of dibenzofuran are compared with specific compounds 21 to 40 and 121 to 140 in which aryl groups and heteroaryl groups excluding carbazole are bonded as substituents to each 4-position of the benzene ring of dibenzofuran, as follows:

[0307] When aryl groups are attached as substituents to all 4-positions of each benzene ring of dibenzofuran, the molecular structure becomes unipolar. On the other hand, when an aryl group is attached to one side and a heteroaryl group to the other, the molecule becomes bipolar, resulting in a better balance of electrons and more frequent charge transfer. However, when aryl groups and heteroaryl groups (excluding carbazole) are attached to the 4-position of each benzene ring of dibenzofuran, the degree to which they donate electrons to the electron-deficient sites of dibenzofuran is similar, and it was confirmed that the driving voltage, efficiency, and lifetime are similar.

[0308] In addition, when an aryl group or a carbazole group, which has a stronger tendency to donate electrons than an aryl group, is used as a substituent at the 4-position of each benzene ring of dibenzofuran, the molecule becomes more electron-rich and structurally more stable. Therefore, it was confirmed that the specific compounds 41 to 80 and 141 to 180 in Table 9 have significantly better driving voltage, efficiency, and lifetime than the specific compounds 1 to 40 and 101 to 140. For the same reason, it was confirmed that when a carbazole group is attached as a substituent to all 4-positions (of the benzene ring) of dibenzofuran, the effect is maximized, resulting in a lower driving voltage and improved lifetime and efficiency.

[0309] Furthermore, the results in Table 11 confirm that the simultaneous inclusion of the compound of Formula 1 and the compound of Formula A results in better efficiency and lifespan. From these results, it can be predicted that the exciplex phenomenon will occur when the two compounds are simultaneously included.

[0310] The exciplex phenomenon is a phenomenon in which electron exchange between two molecules releases energy at the HOMO level of the donor (p-host) and the LUMO level of the acceptor (n-host). When the exciplex phenomenon between two molecules occurs, reverse intersystem crossing (RISC) occurs, which can increase the internal quantum efficiency of fluorescence to 100%. When a donor (p-host) with good hole transporting ability and an acceptor (n-host) with good electron transporting ability are used as the host of the emitting layer, holes are injected into the p-host and electrons are injected into the n-host, which can reduce the driving voltage and thereby improve the lifetime. In the present invention, it has been confirmed that excellent device characteristics are exhibited when the compound represented by Formula A above acts as the donor and the compound represented by Formula 1 above acts as the acceptor, respectively, when used as the host of the emitting layer. [Explanation of symbols]

[0311] 100... Substrate 200...Anode 300...organic layer 301: Hole injection layer 302 Hole transport layer 303 Light-emitting layer 304: Hole blocking layer 305...electron transport layer 306...electron injection layer 400...Cathode

Claims

1. A heterocyclic compound represented by the following chemical formula 1: 【Chemistry 31】 In the above Chemical Formula 1, X is O; or S; N-Het is a substituted or unsubstituted triazine group; a substituted or unsubstituted pyrimidine group; a substituted or unsubstituted pyridine group; a substituted or unsubstituted quinoline group; a substituted or unsubstituted 1,10-phenanthroline group; a substituted or unsubstituted 1,7-phenanthroline group; a substituted or unsubstituted quinazoline group; a substituted or unsubstituted pyrido[3,2-d]pyrimidine; or a substituted or unsubstituted benzimidazole group; Ar1 and Ar2 are the same or different and each independently represent a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group having three or less rings; or a substituted or unsubstituted C2 to C60 heteroaryl group having three or more rings; R3 to R5 are the same or different and are each independently selected from the group consisting of hydrogen and deuterium; L1 to L3 are the same or different and each independently represent a direct bond; or a substituted or unsubstituted C6 to C60 monocyclic arylene group; p and q are integers from 1 to 4, b, m, and n are integers from 0 to 4; a is an integer from 0 to 3, When p, q, a, b, m, and n are 2 or more, the substituents in parentheses are the same or different from each other, and When both -(L1)m-(Ar1)p and -(L2)n-(Ar2)q are unsubstituted phenyl groups, L3 is a direct bond.

2. The heterocyclic compound according to claim 1 , wherein the chemical formula 1 is represented by the following chemical formula 2 or 3: 【Chemistry 32】 【Transformation 33】 In the above Chemical Formulas 2 and 3, The definitions of X, R3 to R5, N-Het, Ar1, Ar2, L1 to L3, a, b, m, n, p, and q are the same as those in Chemical Formula 1, and When both -(L1)m-(Ar1)p and -(L2)n-(Ar2)q are unsubstituted phenyl groups, L3 is a direct bond.

3. The heterocyclic compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulas 4 to 10: 【Transformation 34】 【Chemistry 35】 【Transformation 36】 【Chemistry 37】 【Transformation 38】 【Chemistry 39】 【Chemistry 40】 In the above Chemical Formulas 4 to 10, X, N-Het, R3 to R5, L1 to L3, m, n, p, q, a, and b are the same as those in Chemical Formula 1; X1 and X2 are the same or different and each independently represent O; S; or NR31; Ar3 and Ar4 are the same or different and each independently represent a substituted or unsubstituted C6 to C60 aryl group having three or less rings; R11 to R18 and R21 to R28 are the same or different and each independently represent a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C2 to C60 alkenyl group, a substituted or unsubstituted C2 to C60 alkynyl group, a substituted or unsubstituted C1 to C60 alkoxy group, a substituted or unsubstituted C3 to C60 cycloalkyl group, a substituted or unsubstituted C2 to C60 heterocycloalkyl group, a substituted or unsubstituted C6 to C60 aryl group, and a substituted or unsubstituted C2 to C60 heteroaryl group, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 aliphatic or aromatic heterocycle; R31 is a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; c is an integer of 0 to 3, and when c is 2 or more, the substituents in the parentheses are the same or different from each other, and When both -(L1)m-(Ar3)p and -(L2)n-(Ar4)q are unsubstituted phenyl groups, L3 is a direct bond.

4. The heterocyclic compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following compounds: 【Chemistry 41】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】

5. 10. An organic light-emitting device comprising: a first electrode; a second electrode provided opposite the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein one or more of the organic material layers contains the heterocyclic compound according to claim 1.

6. The organic light-emitting device according to claim 5 , wherein the organic material layer containing a heterocyclic compound further contains a heterocyclic compound represented by the following chemical formula A: 【Chemistry 42】 In the above chemical formula A, Rc and Rd are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, a halogen group, -CN, a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C2 to C60 alkenyl group, a substituted or unsubstituted C2 to C60 alkynyl group, a substituted or unsubstituted C1 to C60 alkoxy group, a substituted or unsubstituted C3 to C60 cycloalkyl group, a substituted or unsubstituted C2 to C60 heterocycloalkyl group, a substituted or unsubstituted C6 to C60 aryl group, a substituted or unsubstituted C2 to C60 heteroaryl group, -SiR201R202R203; -P(=O)R201R202; and -NR201R202, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle; Ra and Rb are the same or different and each independently represent a substituted or unsubstituted C6 to C60 aryl group; -SiR201R202R203; -P(=O)R201R202; or a substituted or unsubstituted C2 to C60 heteroaryl group; R201, R202 and R203 are the same or different and each independently represent hydrogen; deuterium; -CN; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; r and s are integers from 0 to 7; When r and s are 2 or more, the substituents in the brackets may be the same or different.

7. The organic light-emitting device according to claim 6, wherein the heterocyclic compound represented by the chemical formula A is any one selected from the following compounds: 【Chemistry 43】 【change】 【change】 【change】

8. The organic light-emitting device according to claim 6 , wherein R c and R d are hydrogen.

9. The organic light emitting device according to claim 5 , wherein the organic material layer comprises a light emitting layer, and the light emitting layer comprises the heterocyclic compound of Chemical Formula 1.

10. The organic light-emitting device according to claim 5 , wherein the organic layer includes a light-emitting layer, the light-emitting layer includes a host material, and the host material includes the heterocyclic compound of Chemical Formula 1.

11. 6. The organic light-emitting device according to claim 5, further comprising one or more layers selected from the group consisting of an 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.

12. A composition for an organic layer of an organic light-emitting device, comprising the heterocyclic compound according to any one of claims 1 to 4 and a heterocyclic compound represented by the following chemical formula A: 【Chemistry 44】 In the above chemical formula A, Rc and Rd are the same or different and each independently represent a hydrogen atom, a deuterium atom, a halogen atom, -CN, a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C2 to C60 alkenyl group, a substituted or unsubstituted C2 to C60 alkynyl group, a substituted or unsubstituted C1 to C60 alkoxy group, a substituted or unsubstituted C3 to C60 cycloalkyl group, a substituted or unsubstituted C2 to C60 heterocycloalkyl group, a substituted or unsubstituted C6 to C60 aryl group, a substituted or unsubstituted C2 to C60 heteroaryl group, -SiR201R202R203, -P(=O)R201R202, and -NR201R202, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle; Ra and Rb are the same or different and each independently represent a substituted or unsubstituted C6 to C60 aryl group; -SiR201R202R203; -P(=O)R201R202; or a substituted or unsubstituted C2 to C60 heteroaryl group; R201, R202, and R203 are the same or different and each independently represent hydrogen; deuterium; —CN; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; r and s are integers from 0 to 7; When r and s are 2 or more, the substituents in the brackets may be the same or different.

13. The composition for an organic material layer of an organic light-emitting device according to claim 12, wherein a weight ratio of the heterocyclic compound to the heterocyclic compound represented by Chemical Formula A in the composition is 1:10 to 10:

1.

14. providing a substrate; forming a first electrode on the substrate; forming one or more organic layers on the first electrode; and forming a second electrode on the organic layer; A method for manufacturing an organic light-emitting element, wherein the step of forming an organic material layer includes a step of forming one or more organic material layers using the composition for organic material layer according to claim 12.

15. 15. The method for manufacturing an organic light-emitting device according to claim 14, wherein the forming of the organic material layer comprises pre-mixing the heterocyclic compound of Chemical Formula 1 and the heterocyclic compound of Chemical Formula A and forming the organic material layer using a thermal vacuum deposition method.

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