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

Abstract

To provide: a compound for an organic light-emitting element; and a method for manufacturing the organic light-emitting element.SOLUTION: The present specification provides: a heterocyclic compound represented by chemical formula 1; an organic light-emitting element including the heterocyclic compound; a composition for an organic material layer of the organic light-emitting element; and a method for manufacturing the organic light-emitting element.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] This application claims the benefit of the filing date of Korean Patent Application No. 10-2019-0150714, filed with the Korean Intellectual Property Office on November 21, 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 heterocyclic compound, a composition for an organic material layer of the organic light-emitting device, and a method for producing the organic light-emitting device. [Background technology]

[0003] An organic electroluminescent device is a type of self-luminous display device, and has the advantages of 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 may be configured as a single layer or multiple layers as required.

[0005] The organic thin film material may have a light-emitting function as needed. For example, the organic thin film material may be a compound that can form an emitting layer by itself, or a compound that functions as a host or dopant in a host-dopant emitting layer. In addition, the organic thin film material 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 materials that can be used in organic light-emitting devices, such as appropriate energy levels, electrochemical stability, and thermal stability, and that have chemical structures that can perform 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 application relates to a heterocyclic compound, an organic light-emitting device containing the heterocyclic compound, a composition for an organic layer of the organic light-emitting device, and a method for producing the organic light-emitting device. [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, N-Het is a substituted or unsubstituted C2-C60 monocyclic or polycyclic heterocyclic group containing one or more N atoms, L is a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group; a is an integer of 1 to 3, and when a is 2 or more, L's are the same or different; A is a substituted or unsubstituted C6-C60 aryl ring; or a substituted or unsubstituted C2-C60 heteroaryl ring; Ra is 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 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, d is an integer of 0 to 2, and when d is 2, two Ra are the same or different, R1 to R6 are the same or different and each independently represent hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C2 to C60 alkenyl group; substituted or unsubstituted C2 to C60 alkynyl group; substituted or unsubstituted C1 to C60 alkoxy group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or unsubstituted C2 to C60 heterocycloalkyl group; substituted or unsubstituted C6 to C60 aryl group; substituted or unsubstituted C2 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, b is an integer of 0 to 2, c is an integer of 0 to 4, and when b is 2, R5s are the same or different from each other, and when c is 2 or more, R6s are the same or different from each other.

[0012] Furthermore, according to one embodiment of the present application, there is provided an organic light-emitting device including 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 includes at least one heterocyclic compound represented by Chemical Formula 1.

[0013] Furthermore, in one embodiment of the present application, there is provided a composition for an organic layer of an organic light-emitting device, comprising a heterocyclic compound represented by Chemical Formula 1 above and a heterocyclic compound represented by Chemical Formula 2 below.

[0014] [ka] In the above Chemical Formula 2, Ar1 is hydrogen; deuterium; 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; R51 to R58 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; a substituted or unsubstituted phosphine oxide group; and a substituted or unsubstituted amine group, or two or more adjacent groups may be 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.

[0015] Finally, in one embodiment of the present application, there is provided a method for manufacturing an organic light-emitting element, 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 comprises 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]

[0016] 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 of the compounds can be used together as light-emitting materials, and can be used as host materials in the light-emitting layer.

[0017] In particular, the compound of Formula 1 has a highly electronegative O atom in the center of the core structure, which gives it excellent electron transfer ability and makes it suitable for exciton blocking. In addition, when the carbazole structure fused to one of the benzene rings of the dibenzofuran structure is substituted at positions 1 and 3, the HOMO orbital and LUMO orbital can be separated by steric, facilitating electron transfer.

[0018] On the other hand, when the fused carbazole structure is substituted at the 1st and 4th positions of one of the benzene rings of the dibenzofuran, intermolecular π-π stacking effectively occurs, resulting in effective intermolecular electron transfer and thermal stability suitable for devices. Therefore, organic light-emitting devices with improved lifetime, driving stability, and efficiency can be manufactured using the heterocyclic compound of Formula 1. [Brief explanation of the drawings]

[0019] [Figure 1] 1 is a diagram schematically illustrating a stacked structure of an organic light-emitting device according to an embodiment of the present application. [Figure 2] 1 is a diagram schematically illustrating a stacked structure of an organic light-emitting device according to an embodiment of the present application. [Figure 3] 1 is a diagram schematically illustrating a stacked structure of an organic light-emitting device according to an embodiment of the present application. [Figure 4] FIG. 1 is a diagram illustrating an exciplex phenomenon. [Figure 5]1 shows PL (photoluminescence) measurement data of the first host and the second host alone according to Example 71 of the present application. [Figure 6] 1 shows PL (photoluminescence) measurement data for the case where both the first host and the second host are included according to Example 71 of the present application. DETAILED DESCRIPTION OF THE INVENTION

[0020] The present application will be described in detail below.

[0021] 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 Since H (Deuterium) is an isotope of hydrogen, some hydrogen atoms may be deuterium.

[0022] In one embodiment of the present application, "when no substituent is shown in the chemical formula or compound structure," can mean that all positions corresponding to the substituents are hydrogen or deuterium. That is, in the case of deuterium, it is an isotope of hydrogen, and some hydrogen atoms may be deuterium, which is an isotope, and in this case, the content of deuterium may be 0% to 100%.

[0023] In one embodiment of the present application, in the case where "no substituent is represented in the chemical formula or compound structure," hydrogen and deuterium can be used together in the compound if deuterium is not explicitly excluded, such as when the deuterium content is 0% or the hydrogen content is 100%. That is, when it is expressed as "substituent X is hydrogen," it can mean a state in which hydrogen and deuterium are mixed together, without excluding deuterium, such as when the hydrogen content is 100% or the deuterium content is 0%.

[0024] 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 may be represented as hydrogen-2, or its atomic symbol may be written as D or 2H.

[0025] 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.

[0026] 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.

[0027] That is, in one example: [ka] A phenyl group having a deuterium content of 20% is represented by the following structural formula 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 having a deuterium content of 20% may be represented by the following structural formula:

[0028] [ka] In addition, 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.

[0029] As used herein, the halogen may be fluorine, chlorine, bromine, or iodine.

[0030] In this specification, the alkyl group includes a straight or branched chain having 1 to 60 carbon atoms, and may be additionally 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.

[0031] In this specification, the alkenyl group includes a straight or branched chain having 2 to 60 carbon atoms and may be additionally 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.

[0032] In this specification, the alkynyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be additionally substituted with other substituents. The number of carbon atoms in the alkynyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20.

[0033] In this specification, the alkoxy group may be linear, branched, or cyclic. The number of carbon atoms in the alkoxy group is not particularly limited, but those having 1 to 20 carbon atoms are preferred. Specifically, the alkoxy group may be, but is not limited to, methoxy, ethoxy, n-propoxy, 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, p-methylbenzyloxy, etc.

[0034] In this specification, the cycloalkyl group includes a monocyclic or polycyclic group having 3 to 60 carbon atoms and may be additionally substituted with other substituents. Here, the term "polycyclic group" refers to a group in which the cycloalkyl group is directly linked to or condensed with another cyclic group. Here, the other cyclic group may be a cycloalkyl group, but it 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, and 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.

[0035] In this specification, the heterocycloalkyl group contains O, S, Se, N, or Si as a heteroatom, and includes a monocyclic or polycyclic group having 2 to 60 carbon atoms, which may be additionally substituted with other substituents. Here, the term "polycyclic group" refers to a group in which the heterocycloalkyl group is directly linked 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, and more specifically 3 to 20.

[0036] In this specification, the aryl group includes a monocyclic or polycyclic ring having 6 to 60 carbon atoms, and may be additionally substituted with other substituents. Here, the polycyclic ring means a group in which an aryl group is directly linked to or condensed with another cyclic group. Here, the other cyclic group may be an aryl group, but may also be other types of cyclic groups, such as a cycloalkyl group, a heterocycloalkyl group, or a heteroaryl group. The aryl group includes a spiro 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, but are not limited to, 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, a fluorenyl group, an indenyl group, an acenaphthylenyl group, a benzofluorenyl group, a spirobifluorenyl group, a 2,3-dihydro-1H-indenyl group, and fused ring groups thereof.

[0037] In this specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

[0038] When the fluorenyl group is substituted, it may have the following structure, but is not limited to this.

[0039] [ka] In this specification, the heteroaryl group contains S, O, Se, N, or Si as a heteroatom, and includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, which may be additionally substituted with other substituents. Here, the polycyclic ring refers to a group in which the heteroaryl group is directly linked 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, and 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, and a triazinyl group. group, tetrazinyl group, quinolyl group, isoquinolyl group, quinazolinyl group, isoquinazolinyl group, quinozolyl group, naphthyridyl group, acridinyl group, phenanthridinyl group, imidazopyridinyl group, diazanaphthalenyl group, triazaindene group, indolyl group, indolizinyl group, benzothiazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiophene group, benzofuran group, dibenzothiophene group, dibenzofuran group, carbazolyl group, benzocathionyl group, 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, phenothiazinyl group, Examples of such alkyl groups include, but are not limited to, azinyl, 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.

[0040] 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.

[0041] 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.

[0042] 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.

[0043] In this specification, a silyl group is a substituent containing Si and directly linked to the Si atom 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 silyl groups include, but are not limited to, trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl.

[0044] As used herein, the term "adjacent" refers to a substituent substituted on an atom directly connected 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 are considered to be "adjacent" groups.

[0045] The aliphatic or aromatic hydrocarbon ring or heterocycle that can form the adjacent group can have the structures exemplified above as the cycloalkyl group, cycloheteroalkyl group, aryl group, and heteroaryl group, except that it is not a monovalent group.

[0046] 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. When two or more substituents are substituted, the two or more substituents may be the same or different.

[0047] 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 straight-chain or branched-chain alkyl; C2 to C60 straight-chain or branched-chain alkenyl; C2 to C60 straight-chain or branched-chain 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 formed by linking two or more substituents selected from the above-mentioned exemplary substituents.

[0048] In one embodiment of the present application, 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.

[0049] In another embodiment, R, R', and R" are the same or different and each independently represent a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0050] In still another embodiment, R, R', and R" are the same or different and each independently represent a substituted or unsubstituted C1 to C40 alkyl group; or a substituted or unsubstituted C6 to C40 aryl group.

[0051] In still another embodiment, R, R', and R" are the same or different and each independently represent a substituted or unsubstituted C1 to C20 alkyl group; or a substituted or unsubstituted C6 to C20 aryl group.

[0052] In still another embodiment, R, R', and R'' are the same or different and each independently represent a C1 to C20 alkyl group; or a C6 to C20 aryl group.

[0053] In still another embodiment, R, R', and R'' are the same or different and each independently represent a C1 to C10 alkyl group; or a C6 to C10 aryl group.

[0054] In still another embodiment, R, R', and R'' are the same or different and each independently represent a linear C1 to C10 alkyl group; or a monocyclic C6 to C10 aryl group.

[0055] In yet another embodiment, R, R', and R" are the same or different and are each independently a methyl group; or a phenyl group.

[0056] In one embodiment of the present application, there is provided a heterocyclic compound represented by Chemical Formula 1 above.

[0057] In one embodiment of the present application, the chemical formula 1 may be represented by one of the following chemical formulas 3 to 6.

[0058] [ka] [ka] [ka] [ka] In the chemical formulas 3 to 6, the definitions of N-Het, L, A, Ra, R1 to R6, a, b, c, and d are the same as those in the chemical formula 1.

[0059] In particular, when the above substituents are substituted at the 1st and 3rd positions of dibenzofuran as in Chemical Formula 5, the device has excellent life characteristics, efficiency, and drivability.

[0060] In one embodiment of the present application, [ka] may be represented by any one of the following chemical formulas 1-1 to 1-6.

[0061] [ka] [ka] [ka] [ka] [ka] [ka] In the above chemical formulas 1-1 to 1-6, R11 to R14 are the same or different and are each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl 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 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle; R15 to R18 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; Rb is hydrogen; deuterium; or a substituted or unsubstituted C6 to C60 aryl group, and m is an integer of 0 to 4, and when m is 2 or more, the Rb's are the same or different.

[0062] In the above chemical formulas 1-1 to 1-6, [ka] means the position at which the compound is connected to Chemical Formula 1.

[0063] In Chemical Formula 1-1 and Chemical Formula 1-3 of the present application, when R12 and R13 bond to each other to form an unsubstituted C6 to C60 aromatic hydrocarbon ring or an unsubstituted C2 to C60 heterocycle, at least one of R11, R14, R15 to R18, and Rb in Chemical Formula 1-1 and Chemical Formula 1-3 may be selected from the group consisting of deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; and a substituted or unsubstituted C2 to C60 heteroaryl group.

[0064] In Chemical Formula 1-1 and Chemical Formula 1-3 of the present application, when R12 and R13 bond to each other to form an unsubstituted C6 to C40 aromatic hydrocarbon ring, at least one of R11, R14, R15 to R18, and Rb in Chemical Formula 1-1 and Chemical Formula 1-3 may be selected from the group consisting of deuterium; a substituted or unsubstituted C6 to C60 aryl group; and a substituted or unsubstituted C2 to C60 heteroaryl group.

[0065] In Chemical Formula 1-1 and Chemical Formula 1-3 of the present application, when R12 and R13 are bonded to each other to form an unsubstituted benzene ring, at least one of R11, R14, R15 to R18, and Rb in Chemical Formula 1-1 and Chemical Formula 1-3 may be selected from the group consisting of deuterium; a phenyl group; a biphenyl group; and a naphthyl group.

[0066] In one embodiment of the present application, in Chemical Formula 1-1 and Chemical Formula 1-3, R11 to R14 are the same or different and are each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; and a substituted or unsubstituted C2 to C60 heteroaryl group, or R11 and R12; or R13 and R14 may be 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.

[0067] In another embodiment, in Chemical Formula 1-1 and Chemical Formula 1-3, R11 to R14 are the same or different and are each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; and a substituted or unsubstituted C2 to C60 heteroaryl group, or R11 and R12; or R13 and R14 may be bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring.

[0068] In still another embodiment, in Chemical Formula 1-1 and Chemical Formula 1-3, R11 to R14 are each independently selected from the group consisting of hydrogen; deuterium; a phenyl group; a biphenyl group, and a naphthyl group, or R11 and R12; or R13 and R14 may be bonded to each other to form a benzene ring.

[0069] In one embodiment of the present application, N-Het is a substituted or unsubstituted C2 to C60 monocyclic or polycyclic heterocycle containing one or more N atoms.

[0070] In another embodiment, N-Het is a C2-C60 monocyclic or polycyclic heterocycle containing one or more N, which is substituted or unsubstituted with one or more substituents selected from the group consisting of a C6-C60 aryl group and a C2-C60 heteroaryl group.

[0071] In yet another embodiment, N-Het is a C2-C40 monocyclic or polycyclic heterocycle containing one or more N, which is unsubstituted or substituted with one or more substituents selected from the group consisting of a C6-C40 aryl group and a C2-C40 heteroaryl group.

[0072] In yet another embodiment, N-Het is a C2-C30 monocyclic or polycyclic heterocycle containing one or more N, which is unsubstituted or substituted with one or more substituents selected from the group consisting of a C6-C30 aryl group and a C2-C30 heteroaryl group.

[0073] In still another embodiment, N-Het is a C2-C30 monocyclic or polycyclic heterocycle containing one or more N atoms, which is unsubstituted or substituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, a dibenzofuran group, a dibenzothiophene group, and a dimethylfluorenyl group.

[0074] In yet another embodiment, N-Het is a C2-C30 monocyclic or polycyclic heterocycle containing 1 to 3 N atoms, which is substituted or unsubstituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, a dibenzofuran group, a dibenzothiophene group, and a dimethylfluorenyl group.

[0075] In yet other embodiments, N-Het may be a triazine group substituted or unsubstituted with one or more substituents selected from the group consisting of phenyl, biphenyl, naphthyl, dibenzofuran, dibenzothiophene, and dimethylfluorenyl groups.

[0076] In still other embodiments, N-Het is a triazine group substituted or unsubstituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, a dibenzofuran group, a dibenzothiophene group, and a dimethylfluorenyl group; a pyrimidine group substituted or unsubstituted with one or more substituents selected from the group consisting of a phenyl group and a naphthyl group; a quinazoline group substituted or unsubstituted with a phenyl group, a biphenyl group, or a naphthyl group; a quinoline group substituted or unsubstituted with a phenyl group, a biphenyl group, or a naphthyl group; a quinoxaline group substituted or unsubstituted with a phenyl group, a biphenyl group, or a naphthyl group; a benzofuro[3,2-d]pyrimidine group substituted or unsubstituted with a phenyl group, a biphenyl group, or a naphthyl group; a benzofuro[2,3-d]pyrimidine group substituted or unsubstituted with a phenyl group, a biphenyl group, or a naphthyl group; a benzo[4,5]thieno[3,2-d]pyrimidine group substituted or unsubstituted with a phenyl group, a biphenyl group, or a naphthyl group; or a benzo[4,5]thieno[2,3-d]pyrimidine group substituted or unsubstituted with a phenyl group, a biphenyl group, or a naphthyl group.

[0077] In one embodiment of the present application, the benzofuro[3,2-d]pyrimidine group may have the following structure:

[0078] [ka] In one embodiment of the present application, the benzofuro[2,3-d]pyrimidine group may have the following structure:

[0079] [ka] In one embodiment of the present application, the benzo[4,5]thieno[3,2-d]pyrimidine group may have the following structure:

[0080] [ka] In one embodiment of the present application, the benzo[4,5]thieno[2,3-d]pyrimidine group may have the following structure:

[0081] [ka] In one embodiment of the present application, the N-Het may be further substituted with a C6 to C20 aryl group; or deuterium.

[0082] In other embodiments, the N-Het may be further substituted with deuterium; a phenyl group; or a naphthyl group.

[0083] In one embodiment of the present application, the N-Het may be represented by the following chemical formula 2-1:

[0084] [ka] In the above Chemical Formula 2-1, X1 is N or CR21, X3 is N or CR23, and X5 is N or CR25; At least one of X1, X3 and X5 is N; R21 to R25 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0085] In the above Chemical Formula 2-1, [ka] means the position at which it is connected to L in Chemical Formula 1.

[0086] In one embodiment of the present application, the chemical formula 2-1 may be selected from the following structural formulas:

[0087] [ka] In the structural formula: The definitions of R21 to R25 are the same as those in the above chemical formula 2-1.

[0088] In one embodiment of the present application, L may be a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group.

[0089] In other embodiments, L can be a direct bond; a substituted or unsubstituted C6 to C40 arylene group; or a substituted or unsubstituted C2 to C40 heteroarylene group.

[0090] In still other embodiments, L can be a direct bond; a C6 to C40 arylene group; or a C2 to C40 heteroarylene group.

[0091] In still other embodiments, L may be a direct bond; a C6 to C40 monocyclic arylene group; or a C2 to C40 monocyclic heteroarylene group.

[0092] In still other embodiments, L may be a direct bond; or a phenylene group.

[0093] In still other embodiments, L may be a direct bond.

[0094] In still other embodiments, L can be a phenylene group.

[0095] In one embodiment of the present application, when R11 to R15, R18, and Rb in Chemical Formula 1-2 are all hydrogen, or when two adjacent groups among R11 to R14 in Chemical Formula 1-2 are bonded to each other to form an unsubstituted C6 to C60 aromatic hydrocarbon ring or an unsubstituted C2 to C60 heterocycle, N-Het in Chemical Formula 1 may be a substituted or unsubstituted C2 to C60 monocyclic or polycyclic heterocycle containing one to two N atoms.

[0096] In another embodiment, when R11 to R15, R18, and Rb in Chemical Formula 1-2 are all hydrogen atoms, or when two adjacent groups among R11 to R14 in Chemical Formula 1-2 are bonded to each other to form an unsubstituted C6 to C60 aromatic hydrocarbon ring or an unsubstituted C2 to C60 heterocycle, N-Het in Chemical Formula 1 may be a substituted or unsubstituted C2 to C40 monocyclic or polycyclic heterocycle containing one to two N atoms.

[0097] In still another embodiment, when R11 to R15, R18, and Rb in Chemical Formula 1-2 are all hydrogen atoms, or when two adjacent groups among R11 to R14 in Chemical Formula 1-2 are bonded to each other to form an unsubstituted C6 to C60 aromatic hydrocarbon ring or an unsubstituted C2 to C60 heterocycle, N-Het in Chemical Formula 1 may be a substituted or unsubstituted C2 to C20 monocyclic or polycyclic heterocycle containing one to two N atoms.

[0098] In still another embodiment, when R11 to R15, R18, and Rb in Chemical Formula 1-2 are all hydrogen atoms, or when two adjacent groups among R11 to R14 in Chemical Formula 1-2 are bonded to each other to form an unsubstituted C6 to C60 aromatic hydrocarbon ring or an unsubstituted C2 to C60 heterocycle, N-Het in Chemical Formula 1 may be a C2 to C20 monocyclic or polycyclic heterocycle substituted or unsubstituted with a C6 to C20 aryl group and containing one to two N atoms.

[0099] In still another embodiment, when R11 to R15, R18, and Rb in Chemical Formula 1-2 are all hydrogen atoms, or when two adjacent groups among R11 to R14 in Chemical Formula 1-2 are bonded to each other to form an unsubstituted C6 to C60 aromatic hydrocarbon ring or an unsubstituted C2 to C60 heterocycle, N-Het in Chemical Formula 1 is a pyrimidine group substituted or unsubstituted with one or more substituents selected from the group consisting of a phenyl group and a naphthyl group; a quinazoline group substituted or unsubstituted with a phenyl group, a biphenyl group, or a naphthyl group; or a quinazoline group substituted or unsubstituted with a phenyl group, a biphenyl group, or a naphthyl group. a quinoxaline group substituted or unsubstituted with a phenyl group or a naphthyl group; a benzofuro[3,2-d]pyrimidine group substituted or unsubstituted with a phenyl group, a biphenyl group, or a naphthyl group; a benzofuro[2,3-d]pyrimidine group substituted or unsubstituted with a phenyl group, a biphenyl group, or a naphthyl group; a benzo[4,5]thieno[3,2-d]pyrimidine group substituted or unsubstituted with a phenyl group, a biphenyl group, or a naphthyl group; or a benzo[4,5]thieno[2,3-d]pyrimidine group substituted or unsubstituted with a phenyl group, a biphenyl group, or a naphthyl group.

[0100] In one embodiment of the present application, when R11 to R15, R18, and Rb in Chemical Formula 1-2 are all hydrogen, or when two adjacent groups among R11 to R14 in Chemical Formula 1-2 are bonded to each other to form an unsubstituted C6 to C60 aromatic hydrocarbon ring or an unsubstituted C2 to C60 heterocycle, the deuterium content in Chemical Formula 1 may be 10% or more and 100% or less.

[0101] In another embodiment, when R11 to R15, R18, and Rb in Chemical Formula 1-2 are all hydrogen, or when two adjacent groups among R11 to R14 in Chemical Formula 1-2 are bonded to each other to form an unsubstituted C6 to C60 aromatic hydrocarbon ring or an unsubstituted C2 to C60 heterocycle, the deuterium content in Chemical Formula 1 may be 15% or more and 90% or less.

[0102] In still another embodiment, when R11 to R15, R18, and Rb in Chemical Formula 1-2 are all hydrogen, or when two adjacent groups among R11 to R14 in Chemical Formula 1-2 are bonded to each other to form an unsubstituted C6 to C60 aromatic hydrocarbon ring or an unsubstituted C2 to C60 heterocycle, the deuterium content in Chemical Formula 1 may be 20% or more and 80% or less.

[0103] In still another embodiment, when R11 to R15, R18, and Rb in Chemical Formula 1-2 are all hydrogen, or when two adjacent groups among R11 to R14 in Chemical Formula 1-2 are bonded to each other to form an unsubstituted C6 to C60 aromatic hydrocarbon ring or an unsubstituted C2 to C60 heterocycle, the deuterium content in Chemical Formula 1 may be 20% or more and 40% or less.

[0104] In the present application, the deuterium content of Chemical Formula 1 may refer to the ratio of deuterium substitutions among the positions that may be substituted with substituents in Chemical Formula 1. That is, if there are a total of 40 positions in Chemical Formula 1 that may be substituted with substituents and 20 of those positions are substituted with deuterium, the deuterium content of Chemical Formula 1 may be expressed as 50%.

[0105] In one embodiment of the present application, when R11 to R15, R18, and Rb in Chemical Formula 1-2 are all hydrogen, or when two adjacent groups among R11 to R14 in Chemical Formula 1-2 are bonded to each other to form an unsubstituted C6 to C60 aromatic hydrocarbon ring or an unsubstituted C2 to C60 heterocycle, L in Chemical Formula 1 may be a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group.

[0106] In another embodiment, when R11 to R15, R18, and Rb in Chemical Formula 1-2 are all hydrogen atoms, or when two adjacent groups among R11 to R14 in Chemical Formula 1-2 are bonded to each other to form an unsubstituted C6 to C60 aromatic hydrocarbon ring or an unsubstituted C2 to C60 heterocycle, L in Chemical Formula 1 may be a substituted or unsubstituted C6 to C40 arylene group; or a substituted or unsubstituted C2 to C40 heteroarylene group.

[0107] In still another embodiment, when R11 to R15, R18, and Rb in Chemical Formula 1-2 are all hydrogen, or when two adjacent groups among R11 to R14 in Chemical Formula 1-2 are bonded to each other to form an unsubstituted C6 to C60 aromatic hydrocarbon ring or an unsubstituted C2 to C60 heterocycle, L in Chemical Formula 1 may be a substituted or unsubstituted C6 to C20 arylene group; or a substituted or unsubstituted C2 to C20 heteroarylene group.

[0108] In still another embodiment, when R11 to R15, R18, and Rb in Chemical Formula 1-2 are all hydrogen, or when two adjacent groups among R11 to R14 in Chemical Formula 1-2 are bonded to each other to form an unsubstituted C6 to C60 aromatic hydrocarbon ring or an unsubstituted C2 to C60 heterocycle, L in Chemical Formula 1 may be a C6 to C20 arylene group; or a C2 to C20 heteroarylene group.

[0109] In still another embodiment, when R11 to R15, R18, and Rb in Chemical Formula 1-2 are all hydrogen, or when two adjacent groups among R11 to R14 in Chemical Formula 1-2 are bonded to each other to form an unsubstituted C6 to C60 aromatic hydrocarbon ring or an unsubstituted C2 to C60 heterocycle, L in Chemical Formula 1 may be a C6 to C20 arylene group.

[0110] In still another embodiment, when R11 to R15, R18, and Rb in Chemical Formula 1-2 are all hydrogen, or when two adjacent groups among R11 to R14 in Chemical Formula 1-2 are bonded to each other to form an unsubstituted C6 to C60 aromatic hydrocarbon ring or an unsubstituted C2 to C60 heterocycle, L in Chemical Formula 1 may be a phenylene group.

[0111] In one embodiment of the present application, when R11 to R15, R18, and Rb in Chemical Formula 1-2 are all hydrogen, or when two adjacent groups among R11 to R14 in Chemical Formula 1-2 are bonded to each other to form an unsubstituted C6 to C60 aromatic hydrocarbon ring or an unsubstituted C2 to C60 heterocycle, N-Het in Chemical Formula 1 may be a substituted or unsubstituted C2 to C60 monocyclic or polycyclic heterocycle containing one to two N atoms, the deuterium content in Chemical Formula 1 may be 10% or more and 100% or less, or L in Chemical Formula 1 may be a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group.

[0112] In one embodiment of the present application, A may be a substituted or unsubstituted C6 to C60 aryl ring; or a substituted or unsubstituted C2 to C60 heteroaryl ring.

[0113] In other embodiments, A may be a substituted or unsubstituted C6 to C40 aryl ring; or a substituted or unsubstituted C2 to C40 heteroaryl ring.

[0114] In still other embodiments, A can be a substituted or unsubstituted C6 to C40 aryl ring.

[0115] In still other embodiments, A can be a substituted or unsubstituted benzene ring or a substituted or unsubstituted naphthyl ring.

[0116] In still other embodiments, A may be a benzene ring substituted or unsubstituted with a C6 to C30 aryl group, or a naphthyl ring substituted or unsubstituted with a C6 to C30 aryl group.

[0117] In still other embodiments, A can be a benzene ring or a naphthyl ring substituted or unsubstituted with a phenyl group.

[0118] In one embodiment of the present application, A may be further substituted with deuterium.

[0119] In one embodiment of the present application, Ra is 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 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle.

[0120] In other embodiments, Ra is 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 heterocycle.

[0121] In yet another embodiment, Ra is selected from the group consisting of hydrogen; deuterium; and 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.

[0122] In yet another embodiment, Ra is selected from the group consisting of hydrogen; deuterium; and a C6 to C40 monocyclic or polycyclic aryl group, or two or more adjacent groups may be bonded to each other to form a C6 to C40 monocyclic or polycyclic aromatic hydrocarbon ring.

[0123] In still other embodiments, Ra is selected from the group consisting of hydrogen; deuterium; and a phenyl group, or two or more groups adjacent to each other may be bonded to each other to form a benzene ring.

[0124] In one embodiment of the present application, R1 to R4 are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C2 to C60 alkenyl group; substituted or unsubstituted C2 to C60 alkynyl group; substituted or unsubstituted C1 to C60 alkoxy group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or unsubstituted C2 to C60 heterocycloalkyl group; substituted or unsubstituted C6 to C60 aryl group; substituted or unsubstituted C2 to C60 heteroaryl group; substituted or unsubstituted phosphine oxide group; substituted or unsubstituted silyl group; and substituted or unsubstituted amine group, or two or more adjacent groups may be 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.

[0125] In still another embodiment, R1 to R4 are each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl 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 may be 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.

[0126] In still another embodiment, R1 to R4 are each independently selected from the group consisting of hydrogen; deuterium; and a substituted or unsubstituted C6 to C40 aryl group, or two or more adjacent groups may be bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring.

[0127] In still another embodiment, R1 to R4 are each independently selected from the group consisting of hydrogen; deuterium; and monocyclic or polycyclic C6 to C40 aryl groups, or two or more adjacent groups may be bonded to each other to form a monocyclic or polycyclic C6 to C60 aromatic hydrocarbon ring.

[0128] In still another embodiment, R1 to R4 are each independently selected from the group consisting of hydrogen; deuterium; and a monocyclic or polycyclic C6 to C20 aryl group, or two or more adjacent groups may be bonded to each other to form a monocyclic or polycyclic C6 to C30 aromatic hydrocarbon ring.

[0129] In still another embodiment, R1 to R4 are each independently selected from the group consisting of hydrogen; deuterium; a phenyl group; a biphenyl group, and a naphthyl group, or two or more adjacent groups may be bonded to each other to form a benzene ring.

[0130] In one embodiment of the present application, R5 and R6 may be hydrogen.

[0131] In one embodiment of the present application, R5 and R6 may be deuterium.

[0132] In one embodiment of the present application, R5 and R6 may be hydrogen; or deuterium.

[0133] In one embodiment of the present application, R5 and R6 may all be hydrogen.

[0134] In one embodiment of the present application, R5 and R6 may all be deuterium.

[0135] In one embodiment of the present application, the heterocyclic compound of Chemical Formula 1 may be further substituted with deuterium, and in this case, the heterocyclic compound of Chemical Formula 1 may be substituted with deuterium at 10% to 100%.

[0136] In one embodiment of the present application, R11 to R14 are the same or different and each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl 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 may be 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.

[0137] In another embodiment, R11 to R14 are each independently selected from the group consisting of hydrogen; deuterium; and a substituted or unsubstituted C6 to C40 aryl group, or two or more adjacent groups may be bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring.

[0138] In still another embodiment, R11 to R14 are each independently selected from the group consisting of hydrogen; deuterium; and monocyclic or polycyclic C6 to C40 aryl groups, or two or more adjacent groups may be bonded to each other to form a monocyclic or polycyclic C6 to C60 aromatic hydrocarbon ring.

[0139] In still another embodiment, R11 to R14 are each independently selected from the group consisting of hydrogen; deuterium; and a monocyclic or polycyclic C6 to C20 aryl group, or two or more adjacent groups may be bonded to each other to form a monocyclic or polycyclic C6 to C30 aromatic hydrocarbon ring.

[0140] In still another embodiment, R11 to R14 are each independently selected from the group consisting of hydrogen; deuterium; a phenyl group; a biphenyl group, and a naphthyl group, or two or more adjacent groups may be bonded to each other to form a benzene ring.

[0141] In one embodiment of the present application, R15 to R18 are the same or different and may each independently represent hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0142] In other embodiments, R15 to R18 are the same or different and may each independently be hydrogen; deuterium; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0143] In still other embodiments, R15 to R18 are the same or different and may each independently be hydrogen; deuterium; a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0144] In still other embodiments, R15 to R18 may be the same or different and may each independently be hydrogen; deuterium; a C6 to C40 aryl group; or a C2 to C40 heteroaryl group.

[0145] In still another embodiment, R15 to R18 may be the same or different and may each independently be hydrogen; deuterium; or a monocyclic or polycyclic C6 to C40 aryl group.

[0146] In still other embodiments, R15 to R18 may be the same or different and may each independently be hydrogen; deuterium; or a phenyl group.

[0147] In one embodiment of the present application, Rb may be hydrogen; deuterium; or a substituted or unsubstituted C6-C60 aryl group.

[0148] In other embodiments, Rb can be hydrogen; deuterium; or a substituted or unsubstituted C6-C40 aryl group.

[0149] In still other embodiments, Rb can be hydrogen; deuterium; or a substituted or unsubstituted C6-C20 aryl group.

[0150] In still other embodiments, Rb can be hydrogen; deuterium; or a C6-C20 aryl group.

[0151] In still other embodiments, Rb can be hydrogen; deuterium; or a C6-C20 monocyclic or polycyclic aryl group.

[0152] In still other embodiments, Rb can be hydrogen; deuterium; or a phenyl group.

[0153] In one embodiment of the present application, R21 to R25 are the same or different and may each independently represent hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0154] In other embodiments, R21 to R25 are the same or different and may each independently be hydrogen; deuterium; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0155] In still another embodiment, R21 to R25 are the same or different and may each independently represent hydrogen; deuterium; a C6 to C60 aryl group substituted or unsubstituted with deuterium, a C1 to C60 alkyl group, or a C6 to C60 aryl group; or a C2 to C60 heteroaryl group.

[0156] In still another embodiment, R21 to R25 are the same or different and may each independently be hydrogen; deuterium; a C6 to C40 aryl group unsubstituted or substituted with deuterium, a C1 to C10 alkyl group, or a C6 to C20 aryl group; or a C2 to C40 heteroaryl group.

[0157] In still another embodiment, R21 to R25 may be the same or different and each independently represent hydrogen; deuterium; a phenyl group unsubstituted or substituted with deuterium or a naphthyl group; a naphthyl group unsubstituted or substituted with a phenyl group; a biphenyl group; a dibenzofuran group; a dibenzothiophene group; or a dimethylfluorenyl group.

[0158] In one embodiment of the present application, X1, X3 and X5 may be N.

[0159] In one embodiment of the present application, at least two of X1, X3 and X5 may be N.

[0160] According to one embodiment of the present application, the above-mentioned Chemical Formula 1 may be represented by any one of the following compounds, but is not limited thereto:

[0161] [ka] TIFF0007800950000026.tif126165 TIFF0007800950000027.tif231165 TIFF0007800950000028.tif149165 TIFF0007800950000029.tif219165 TIFF0007800950000030.tif129165 TIFF0007800950000031.tif218165 TIFF0007800950000032.tif121165 TIFF0007800950000033.tif219165 TIFF0007800950000034.tif219165 TIFF0007800950000035.tif218165 TIFF0007800950000036.tif168165 TIFF0007800950000037.tif204165 TIFF0007800950000038.tif128165 TIFF0007800950000039.tif163165 TIFF0007800950000040.tif254165 Furthermore, by introducing various substituents into the structure of Chemical Formula 1, it is possible to synthesize compounds having the unique properties of the introduced substituents. For example, by introducing into the core structure substituents that are primarily used in hole injection layer materials, hole transport layer 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 meet the requirements of each organic material layer.

[0162] Furthermore, by introducing various substituents into the structure of Chemical Formula 1, the energy band gap can be finely adjusted, while the properties at the interface between organic materials can be improved, thereby diversifying the uses of the material.

[0163] In addition, one embodiment of the present application provides an organic light-emitting device including 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 includes at least one heterocyclic compound represented by Chemical Formula 1.

[0164] In another embodiment, there is provided 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 at least one of the organic material layers comprises one heterocyclic compound represented by Chemical Formula 1.

[0165] In yet another embodiment, there is provided 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 at least one of the organic material layers comprises two heterocyclic compounds represented by Chemical Formula 1.

[0166] When the organic light-emitting device contains two or more heterocyclic compounds, the types of the heterocyclic compounds may be the same or different.

[0167] The specific details regarding the heterocyclic compound represented by Chemical Formula 1 are the same as those described above.

[0168] In one embodiment of the present application, the first electrode may be an anode and the second electrode may be a cathode.

[0169] In other embodiments, the first electrode may be a cathode and the second electrode may be an anode.

[0170] In one embodiment of the present application, the organic light emitting device may be a blue organic light emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material for the blue organic light emitting device. For example, the heterocyclic compound represented by Chemical Formula 1 may be included in a host material of a blue light emitting layer of the blue organic light emitting device.

[0171] 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 of the green organic light emitting device. For example, the heterocyclic compound represented by Chemical Formula 1 may be included in a host material of a green light emitting layer of the green organic light emitting device.

[0172] 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 of the red organic light emitting device. For example, the heterocyclic compound represented by Chemical Formula 1 may be included in a host material of a red light emitting layer of the red organic light emitting device.

[0173] The organic light-emitting device of the present invention can be manufactured by a conventional method and material for manufacturing an organic light-emitting device, except that one or more organic layers are formed using the heterocyclic compound described above.

[0174] The heterocyclic compound may be formed in an organic layer by a solution coating method, such as a vacuum deposition method, or a solution coating method, including, but not limited to, spin coating, dip coating, inkjet printing, screen printing, spraying, and roll coating, during the manufacture of an organic light emitting device.

[0175] The organic material layer of the organic light-emitting device of the present invention may have a single-layer structure or 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 the organic material layer. However, the structure of the organic light-emitting device is not limited thereto and may include fewer organic material layers.

[0176] 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 the heterocyclic compound.

[0177] In another organic light-emitting device, the organic material layer may include a light-emitting layer, the light-emitting layer may include a host material, and the host material may include the heterocyclic compound.

[0178] As another example, the organic layer containing the heterocyclic compound includes the heterocyclic compound represented by Chemical Formula 1 as a host, and can be used together with an iridium-based dopant.

[0179] 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 transport layer or the electron injection layer may include the heterocyclic compound.

[0180] 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.

[0181] 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.

[0182] 1 to 3 show 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 figures 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.

[0183] 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.

[0184] Figure 3 illustrates an example of a multi-layer organic material layer. The organic light-emitting device of Figure 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.

[0185] The organic layer containing the compound of Formula 1 may further contain other materials as needed.

[0186] In the organic light emitting device according to one embodiment of the present application, the organic material layer may further include a heterocyclic compound represented by the following Chemical Formula 2:

[0187] [ka] In the above Chemical Formula 2, Ar1 is hydrogen; deuterium; 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; R51 to R58 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; a substituted or unsubstituted phosphine oxide group; and a substituted or unsubstituted amine group, or two or more adjacent groups may be 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.

[0188] In particular, an exciplex phenomenon occurs when the compound further contains a heterocyclic compound of Formula 2. The exciplex phenomenon refers to the formation of an excited heterocomplex due to electron exchange between a molecule having strong donor properties and a molecule having strong acceptor properties.

[0189] Figure 4 is a diagram illustrating the exciplex phenomenon. When the exciplex phenomenon occurs, as shown in Figure 4, new S1 and T1 energy levels are formed, and changes in the red-shifted PL can be observed from each molecule.

[0190] That is, when an exciplex, which is a heterocomplex in an excited state, is formed between a donor and an acceptor molecule, it has a new energy level different from the energy levels of the donor and acceptor, and the light emitted at this energy level is red-shifted compared to the light emitted by the donor and acceptor, and PL is measured to confirm this. Therefore, by comparing the emission wavelength of a single host with that of a mixed host from the PL data, it can be determined whether an exciplex has formed in this molecule.

[0191] When an exciplex phenomenon occurs between two molecules in this way, reverse intersystem crossing (RISC) occurs, which can increase the internal quantum efficiency to 100%.

[0192] In particular, the compound of Formula 1 is a bipolar compound with strong acceptor ability, but by injecting the donor (p-host), which is a heterocyclic compound of Formula 2 with good hole transport ability, it exhibits a red-shifted PL change, forming an exciplex, which can help improve light-emitting properties. Also, by injecting the compound (donor (p-host)) corresponding to Formula 2 of the present application with good hole transport ability, the light-emitting zone in the light-emitting layer moves appropriately, significantly improving the lifetime.

[0193] In one embodiment of the present application, the chemical formula 2 may be represented by any one of the following chemical formulas 10 to 12.

[0194] [ka] [ka] [ka] In the above chemical formulas 10 to 12, R61 to R70 are the same or different and are each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; and a substituted or unsubstituted C2 to C60 heteroaryl group; R71 to R74 are the same or different and are each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl 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 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle; Ar2 and Ar3 are the same or different and each independently represent hydrogen; deuterium; 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; A1 is O; S; NAr4; or CRdRe; Rd and Re are the same or different and each independently represent a substituted or unsubstituted C1 to C60 alkyl group; or a substituted or unsubstituted C6 to C60 aryl group, Ar4 is hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; h and i are integers from 0 to 3, j is an integer from 0 to 2.

[0195] In one embodiment of the present application, the above-mentioned Chemical Formula 10 may be represented by the following Chemical Formula 10-1 or 10-2.

[0196] [ka] [ka] In the above chemical formulas 10-1 and 10-2, The definition of each substituent is the same as that in Chemical Formula 10 above.

[0197] In one embodiment of the present application, the above-mentioned chemical formula 11 may be represented by the following chemical formula 11-1 or 11-2.

[0198] [ka] [ka] In the above chemical formulas 11-1 and 11-2, The definition of each substituent is the same as that in Chemical Formula 11 above.

[0199] In one embodiment of the present application, the chemical formula 12 may be represented by any one of the following chemical formulas 12-1 to 12-4.

[0200] [ka] [ka] [ka] [ka] In the chemical formulas 12-1 to 12-4, The definitions of Ar2 and A1 are the same as those in Chemical Formula 12 above. R81 and R82 are the same or different, and each independently represents a substituted or unsubstituted C10 or higher aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; R83 is a substituted or unsubstituted less than C10 aryl group.

[0201] In one embodiment of the present application, Ar2 to Ar4 may be the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0202] In another embodiment, Ar2 to Ar4 may be the same or different and may each independently represent hydrogen; deuterium; a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0203] In still another embodiment, Ar2 to Ar4 may be the same or different and each independently represent hydrogen; deuterium; a C6 to C40 aryl group substituted or unsubstituted with one or more substituents selected from the group consisting of a halogen group, a C1 to C20 alkyl group, a C6 to C40 aryl group, and a C2 to C40 heteroaryl group; or a C2 to C40 heteroaryl group substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a C6 to C40 aryl group, and a C2 to C40 heteroaryl group.

[0204] In one embodiment of the present application, R61 to R70 may be hydrogen or deuterium.

[0205] In one embodiment of the present application, R71 to R74 are the same or different and each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl 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 may be 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.

[0206] In another embodiment, R71 to R74 are the same or different and each independently represent hydrogen or deuterium; or two or more adjacent groups may be 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.

[0207] In still another embodiment, R71 to R74 are the same or different and each independently represent hydrogen or deuterium; or two or more adjacent groups may be bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring.

[0208] In still another embodiment, R71 to R74 are the same or different and each independently represent hydrogen or deuterium, or two or more adjacent groups may be bonded to each other to form a C6 to C60 aromatic hydrocarbon ring.

[0209] In still another embodiment, R71 to R74 are the same or different and each independently represent hydrogen or deuterium, or two or more adjacent groups may be bonded to each other to form a C6 to C40 aromatic hydrocarbon ring.

[0210] In still another embodiment, R71 to R74 are the same or different and each independently represent hydrogen or deuterium; or two or more adjacent groups may be bonded to each other to form a benzene ring.

[0211] In one embodiment of the present application, Rd and Re may be the same or different, and each independently may be a substituted or unsubstituted C1 to C60 alkyl group; or a substituted or unsubstituted C6 to C60 aryl group.

[0212] In another embodiment, Rd and Re may be the same or different and may each independently be a substituted or unsubstituted C1 to C60 alkyl group.

[0213] In still another embodiment, Rd and Re may be the same or different and may each independently be a C1 to C40 alkyl group.

[0214] In yet another embodiment, Rd and Re may be methyl groups.

[0215] In one embodiment of the present application, R81 and R82 may be the same or different, and each independently may be a substituted or unsubstituted C10 or higher aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0216] In another embodiment, R81 and R82 may be the same or different and each independently may be a substituted or unsubstituted C10 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0217] In still another embodiment, R81 and R82 may be the same or different and each independently may be a substituted or unsubstituted C10 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0218] In still another embodiment, R81 and R82 may be the same or different and each independently be an aryl group having from 10 to 40 carbon atoms, substituted or unsubstituted with a C1 to C20 alkyl group; or a heteroaryl group having from 2 to 40 carbon atoms, substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group having from 6 to 40 carbon atoms and a heteroaryl group having from 2 to 40 carbon atoms.

[0219] In still another embodiment, R81 and R82 may be represented by the following chemical formula 13:

[0220] [ka] In the above Chemical Formula 13, A2 is NR96;O;S; or CR97R98, R91 to R95 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted C6 to C60 aryl group; or 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 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle; R96 to R98 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; k is an integer of 0 to 3.

[0221] In one embodiment of the present application, said R83 is a substituted or unsubstituted less than C10 aryl group.

[0222] In another embodiment, R83 is a C6 to C10 aryl group or a C2 to C20 heteroaryl group or an aryl group of less than C10 unsubstituted or substituted with a C6 to C10 aryl group or a C2 to C20 heteroaryl group.

[0223] In still other embodiments, R83 may be a phenyl group or a phenyl group unsubstituted or substituted with a dibenzofuran group; a biphenyl group; or a naphthyl group.

[0224] In one embodiment of the present application, R91 to R95 are the same or different and each independently represent hydrogen; deuterium; or a substituted or unsubstituted C6 to C60 aryl group, or two or more adjacent groups may be bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring.

[0225] In one embodiment of the present application, R91 to R95 are the same or different and each independently represent hydrogen or deuterium; or two or more adjacent groups may be bonded to each other to form a benzene ring.

[0226] In one embodiment of the present application, R96 to R98 may be the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0227] In another embodiment, R96 to R98 may be the same or different and may each independently represent hydrogen; deuterium; a C1 to C20 alkyl group; or a C6 to C40 aryl group substituted or unsubstituted with one or more substituents selected from the group consisting of a C1 to C20 alkyl group, a C6 to C40 aryl group, and a C2 to C40 heteroaryl group.

[0228] In one embodiment of the present application, the heterocyclic compound represented by Chemical Formula 2 may be any one of the following compounds:

[0229] [ka] JPEG0007800950000055.jpg77165 In the organic light emitting device according to one embodiment of the present application, the compound of Chemical Formula 2 may be contained in the light emitting layer of the organic material layer.

[0230] In the organic light emitting device according to one embodiment of the present application, the compound of Chemical Formula 2 may be included in the light emitting layer of the organic material layer, and specifically, may be used as a host material of the light emitting layer.

[0231] In one embodiment of the present application, the host material of the light-emitting layer of the organic light-emitting device may include the heterocyclic compound of Chemical Formula 1 and the heterocyclic compound of Chemical Formula 2 simultaneously.

[0232] In one embodiment of the present application, there is provided a composition for an organic layer of an organic light-emitting device, comprising a heterocyclic compound represented by Chemical Formula 1 and a compound represented by Chemical Formula 2.

[0233] The weight ratio of the heterocyclic compound represented by Chemical Formula 1 to the heterocyclic compound represented by Chemical Formula 2 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.

[0234] 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 comprises forming one or more organic material layers using a composition for an organic material layer according to one embodiment of the present application.

[0235] 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 represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 and forming the organic material layer using a thermal vacuum deposition method.

[0236] The term "pre-mixed" means that the heterocyclic compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 are first mixed and placed in a single source before being deposited on an organic layer.

[0237] The premixed materials are referred to as an organic layer composition according to one embodiment of the present application.

[0238] In the organic light-emitting device according to one embodiment of the present application, materials other than the compound of Chemical Formula 1 are exemplified below, but these are for illustrative purposes only and are not intended to limit the scope of the present application. Materials known in the art may be used instead.

[0239] 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.

[0240] 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 structures such as LiF / Al or LiO / Al.

[0241] 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 polymers such as 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.

[0242] As the hole transport material, pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, etc. can be used, and low-molecular or high-molecular materials may also be used.

[0243] 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 substances but also high molecular weight substances may be used.

[0244] As the electron injection material, for example, LiF is typically used in the industry, but the present application is not limited thereto.

[0245] The light-emitting material may be a red, green, or blue light-emitting material, and two or more light-emitting materials may be mixed together if necessary. In this case, two or more light-emitting materials may be deposited as separate sources or 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.

[0246] When a mixture of hosts of light-emitting materials is used, the mixture may be of the same type or different types. For example, two or more of n-type host materials or p-type host materials may be selected and used as the host material of the light-emitting layer.

[0247] The organic light emitting device according to an embodiment of the present application may be a front-emitting type, a back-emitting type, or a dual-side emitting type, depending on the materials used.

[0248] The heterocyclic compound according to one embodiment of the present application can also function in organic electronic devices including organic solar cells, organic photoreceptors, organic transistors, etc., based on a principle similar to that applied to organic light-emitting devices. [Example]

[0249] The present invention will be described in more detail below through examples, but these examples are merely for the purpose of illustrating the present application and are not intended to limit the scope of the present application.

[0250] <Production example> <Production Example 1> Production of Compound 1 [ka]

[0251] 1) Preparation of Compound 1-5 200.0 g (596.4 mmol) of 1-bromo-5-chloro-3-fluoro-2-iodobenzene, 82.4 g (542.2 mmol) of (2-methoxyphenyl)boronic acid, 31.3 g (27.1 mmol) of Pd(PPh), and 150.0 g (1084.4 mmol) of KCO were dissolved in 1 L of 1,4-dioxane / HO (200 mL) and refluxed for 24 h. After completion of the reaction, the mixture was extracted with distilled water and dichloromethane (DCM) at room temperature. The organic layer was dried over MgSO and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex=1:10) to obtain 137 g (80%) of the target compound 1-5.

[0252] 2) Preparation of Compound 1-4 Compound 1-5 (82 g, 259.8 mmol) and BBr (349 mL, 519.7 mol) were dissolved in DCM (800 mL) and refluxed for 1 hour. 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 = 1:1) to yield 65.3 g (83%) of the target compound 1-4.

[0253] 3) Preparation of Compound 1-3 Compound 1-4 (65.3 g, 216.5 mM) and KCO (59.9 g, 433.1 mmol) were dissolved in 300 mL of dimethylformamide (DMF) and refluxed for 4 hours. After the reaction was complete, the mixture was extracted with distilled water and DCM at room temperature. The organic layer was dried over MgSO and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex = 1:5) and recrystallized from methanol to yield 54.8 g (90%) of the target compound 1-3.

[0254] 4) Preparation of Compound 1-2 Compound 1-3 (20.0 g, 70 mmol), bis(pinacolato)diboron (23 g, 92 mmol), Pd(dppf)Cl (22.6 g, 3.55 mmol), and KOAc (20.9 g, 213 mmol) were dissolved in 1,4-dioxane (350 mL) and refluxed for 2 hours. After completion of the reaction, the mixture was extracted with distilled water and DCM at room temperature. The organic layer was dried over MgSO4 and the solvent was removed on a rotary evaporator. The reaction mixture was purified on silica gel and recrystallized from hexane to yield 20.7 g (89%) of the desired compound 1-2.

[0255] 5) Preparation of Compound 1-1 Compound 1-2 (10.7 g, 32.6 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (8.7 g, 32.6 mmol), Pd(PPh)₄ (1.88 g, 1.63 mmol), and K₂CO₃ (13.5 g, 98 mmol) were dissolved in 1,4-dioxane / HO (160 mL / 30 mL) and refluxed for 6 hours. After the reaction was complete, the resulting solid was filtered and washed with dioxane / distilled water / acetone to yield 12.4 g (88%) of the target compound 1-1.

[0256] 6) Preparation of Compound 1 6 g (13.8 mmol) of compound 1-1, 3 g (13.8 mmol) of 5H-benzo[b]carbazole, 1.2 g (1.38 mmol) of Pd2(dba)3, 1.3 g (2.8 mmol) of Xphos, and 4 g (41.4 mmol) of NaPtBu were dissolved in 70 mL of xylene and refluxed for 12 hours. After the reaction was complete, the resulting solid was filtered, washed with distilled water, and dried. The dried solid was dissolved in dichloromethane (DCB) at a boiling point and purified on silica gel. The solvent was then removed using a rotary evaporator. Recrystallization from acetone yielded 7.8 g (86%) of the target compound 1.

[0257] Target compound A was synthesized in the same manner as in Production Example 1, except that intermediate A in Table 1 below was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine and intermediate B in Table 1 below was used instead of 5H-benzo[b]carbazole.

[0258] [Table 1] JPEG0007800950000058.jpg204165 JPEG0007800950000059.jpg218165 JPEG0007800950000060.jpg198165 JPEG0007800950000061.jpg186165 JPEG0007800950000062.jpg219165 JPEG0007800950000063.jpg220165 JPEG0007800950000064.jpg105165

[0259] <Production Example 2> Production of Compound 21 [ka]

[0260] 1) Preparation of Compound 21-2 Compound 21-3 (11.0 g, 39.1 mmol), 5H-benzo[b]carbazole (8.49 g, 39.1 mmol), CuI (7.44 g, 39.1 mmol), trans-1,2-cyclohexanediamine (4.46 g, 39.1 mmol), and KPO (16.59 g, 78.14 mmol) were dissolved in 200 mL of xylene and refluxed for 24 hours. After completion of the reaction, the mixture was extracted with distilled water and DCM at room temperature. The organic layer was dried over MgSO and the solvent was removed using a rotary evaporator. The reaction mixture was purified by column chromatography (DCM:Hex = 1:4) and recrystallized from methanol to yield 12.4 g (76%) of the target compound 21-2.

[0261] 2) Preparation of Compound 21-1 Compound 21-2 (12.4 g, 29.7 mmol), bis(pinacolato)diboron (8.29 g, 32.64 mmol), Pd2(dba)3 (1.36 g, 1.48 mmol), PCy3 (1.25 g, 4.45 mmol), and KOAc (5.82 g, 59.3 mmol) were dissolved in 200 mL of 1,4-dioxane and refluxed for 4 hours. After completion of the reaction, the mixture was extracted with distilled water and DCM at room temperature. The organic layer was dried over MgSO4 and the solvent was removed on a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex = 1:3) and recrystallized from methanol to yield 13.5 g (89%) of the target compound 21-1.

[0262] 3) Preparation of Compound 21 Compound 21-1 (13.5 g, 26.4 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (7.8 g, 29.0 mM), Pd(PPh) (1.53 g, 1.3 mmol), and KCO (7.33 g, 53.0 mM) were dissolved in 1,4-dioxane / HO (150 mL / 30 mL) and refluxed for 4 hours. After the reaction was complete, the resulting solid was washed with distilled water and acetone and dried. The dried solid was dissolved in dichloromethane (DCB) and purified on silica gel. The solvent was removed by rotary evaporation. Recrystallization from methanol afforded 13.4 g (82%) of the target compound 21.

[0263] Target compound A was synthesized in the same manner as in Production Example 2, except that in Production Example 2, intermediate A in Table 2 below was used instead of 5H-benzo[b]carbazole and intermediate B in Table 2 below was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0264] [Table 2] JPEG0007800950000067.jpg207165 JPEG0007800950000068.jpg126165

[0265] <Production Example 3> Production of Compound 51 [ka] Synthesis was performed in the same manner as in Production Example 1, except that 1-bromo-4-chloro-3-fluoro-2-iodobenzene was used instead of 1-bromo-5-chloro-3-fluoro-2-iodobenzene.

[0266] The target compound was synthesized in the same manner as in Production Example 3, except that Intermediate A and Intermediate B in Table 3 below were used.

[0267] [Table 3] JPEG0007800950000071.jpg214165 JPEG0007800950000072.jpg208165 JPEG0007800950000073.jpg210165 JPEG0007800950000074.jpg193165 JPEG0007800950000075.jpg209165 JPEG0007800950000076.jpg102165

[0268] <Production Example 4> Production of Compound 76 [ka] Synthesis was performed in the same manner as in Production Example 2, except that 1-bromo-4-chloro-3-fluoro-2-iodobenzene was used instead of 1-bromo-5-chloro-3-fluoro-2-iodobenzene.

[0269] The target compound was synthesized in the same manner as in Preparation Example 4, except that Intermediate A and Intermediate B in Table 4 below were used.

[0270] [Table 4] JPEG0007800950000079.jpg193165 JPEG0007800950000080.jpg149165 Compounds 1 to 225 and 301 to 624 other than the compounds described in Preparation Examples 1 to 4 and Tables 1 to 4 were also prepared in the same manner as in the above-mentioned Preparation Examples.

[0271] The synthesis confirmation data for the compounds prepared above are as shown in Tables 5 and 6 below.

[0272] [Table 5] TIFF0007800950000082.tif253165 TIFF0007800950000083.tif253165 TIFF0007800950000084.tif75165 [Table 6] TIFF0007800950000086.tif255165 TIFF0007800950000087.tif254165 TIFF0007800950000088.tif251165 TIFF0007800950000089.tif114165

[0273] <Example> 1) Preparation of organic light-emitting device (red host) 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 adjust the ITO work function and remove any remaining film, before being transferred to a thermal evaporation system for organic deposition.

[0274] On the ITO transparent electrode (anode), a common layer consisting of a hole injection layer 2-TNATA (4,4',4"-Tris[2-naphthyl(phenyl)amino]triphenylamine) and a hole transport layer NPB (N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine) was formed.

[0275] An emitting layer was then formed thereon by thermal vacuum deposition as follows: The emitting layer was formed by doping the host with a compound listed in Table 8 below and (piq)2(Ir)(acac) as a red phosphorescent dopant at a weight ratio of 3%. The emitting layer was deposited to a thickness of 500 Å. Then, 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.

[0276] Finally, lithium fluoride (LiF) was deposited on the electron transport layer to a thickness of 10 Å to form an electron injection layer, and then an aluminum (Al) cathode was deposited on the electron injection layer to a thickness of 1,200 Å to form a cathode, thereby completing the manufacture of an organic electroluminescent device.

[0277] 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.

[0278] 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 determine whether the reference luminance was 6,000 cd / m or less using a Mac Science M6000 lifespan measurement device. 2 The HOMO, LUMO and Band Gap of the organic compound of the present invention are as shown in Table 7 below.

[0279] [Table 7] [ka] The HOMO, LUMO, and band gap of the comparative compounds and the example compounds can be seen from Table 7. The results show that the heterocyclic compound of Chemical Formula 1 according to the present application exhibits a greater conjugation effect as the benzene ring of the carbazole is extended (condensed), resulting in a smaller band gap and a smaller T1 level than the comparative compounds A to F, making it suitable as a red host for organic light-emitting devices.

[0280] Table 8 below shows an example in which a single host material was used, and Table 9 shows an example in which two host compounds were deposited as a single supply source, with the first host being a compound (acceptor(n-host)) corresponding to Chemical Formula 1 of the present invention, which has good electron transport ability, and the second host being a compound (donor(p-host)) corresponding to Chemical Formula 2 of the present invention, which has good hole transport ability.

[0281] [Table 8] TIFF0007800950000093.tif213165 As can be seen from Table 8, when the compound of Formula 1 is included in the organic material layer of an organic light emitting device, it can be confirmed that the driving voltage, efficiency, and lifetime are significantly improved. This result is due to the bipolar nature of having a donor with good hole transport ability and an acceptor with good electron transport ability in one molecule, which can efficiently transport electrons and holes and help improve light emitting characteristics. In addition, by extending a benzene ring to the donor with good hole transport ability, it is possible to adjust the HOMO level and minimize the trapping phenomenon that occurs at the contact interface, and it is possible to effectively form a light emitting zone in the light emitting layer, thereby improving lifetime.

[0282] [Table 9] TIFF0007800950000095.tif164165 Table 9 confirms that the driving voltage, efficiency, and lifetime are improved when the heterocyclic compound of Formula 1 and the heterocyclic compound of Formula 2 are simultaneously contained in the organic material layer of the organic light emitting device. This result suggests that the exciplex phenomenon occurs when the two compounds are simultaneously contained.

[0283] The exciplex phenomenon refers to the formation of an excited heterocomplex due to electron exchange between a molecule having strong donor properties and a molecule having strong acceptor properties.

[0284] Figure 4 is a diagram illustrating the exciplex phenomenon. When the exciplex phenomenon occurs, as shown in Figure 4, new S1 and T1 energy levels are formed, and changes in the red-shifted PL can be observed from each molecule.

[0285] Specifically, FIG. 5 shows PL (photoluminescence) measurement data for the first host and the second host alone according to Example 71 of the present application, and FIG. 6 shows PL (photoluminescence) measurement data for the case where both the first host and the second host are included according to Example 71 of the present application.

[0286] As can be seen from FIGS. 5 and 6, when a compound corresponding to Chemical Formula 1 of the present application (first host) and a compound corresponding to Chemical Formula 2 of the present application (second host) were used simultaneously, a red shift was observed compared to when a single host was used.

[0287] When an exciplex phenomenon occurs between two molecules, reverse intersystem crossing (RISC) occurs, which can increase the internal quantum efficiency to 100%. This confirmed that the mixed host has the advantage of increasing the internal quantum efficiency through exciplex formation compared to a single host.

[0288] In particular, the compound of Formula 1 is a bipolar compound that does not have strong acceptor ability, but by injecting the donor (p-host) of the compound of Formula 2, which has good hole transport ability, it shows a red-shifted PL change, and can form an exciplex, which can help improve light-emitting properties.In addition, it was confirmed that the lifetime was significantly improved due to the appropriate movement of the light-emitting zone in the light-emitting layer by injecting the compound (donor (p-host)) corresponding to Formula 2 of the present application, which has good hole transport ability.

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

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

[0291] An emitting layer was then formed thereon by thermal vacuum deposition as follows. Specifically, the compounds listed in Examples 1 to 26 in Table 10 below were used as the red host for the emitting layer, and the red host was doped with 3 wt% of the red phosphorescent dopant (piq)2(Ir)(acac) to deposit an emitting layer with a thickness of 500 Å. Then, bathocuproine (hereinafter referred to as 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.

[0292] Finally, lithium fluoride (LiF) was deposited on the electron transport layer to a thickness of 10 Å to form an electron injection layer, and then an aluminum (Al) cathode was deposited on the electron injection layer to a thickness of 1,200 Å to form a cathode, thereby completing the manufacture of an organic light emitting device.

[0293] 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.

[0294] 2) Driving voltage and luminous efficiency of organic light-emitting devices The electroluminescence (EL) characteristics of the organic light-emitting devices of Examples 1 to 26 manufactured as described above were measured using a Mac Science M7000. Based on the measurement results, a reference luminance of 6,000 cd / m was measured using a Mac Science M6000 lifespan measurement device. 2 At that time, T 90 The T 90 means the lifespan (unit: h) until the brightness becomes 90% of the initial brightness.

[0295] The measured characteristics of the organic light emitting device are shown in Table 10 below.

[0296] [Table 10] As can be seen from Table 10, when the heterocyclic compound of Formula 1 is included in the organic material layer of an organic light-emitting device, it can be confirmed that the driving voltage, efficiency, and lifetime are improved. Weakening the acceptor involved in electron transport ability as in Examples 1 to 11 can help to adjust the HOMO and LUMO levels and form an appropriate threshold voltage. In addition, it can be confirmed that adjusting the acceptor properties of the bipolar host as in Examples 1 to 11 effectively balances the charge balance within the device, thereby further increasing the efficiency and lifetime.

[0297] Increasing intramolecular conjugation, as in Examples 12 to 22 in Table 10, affects the electron transport ability and hole transport ability, respectively. In addition, it was confirmed that controlling the HOMO and LUMO levels minimizes the trapping phenomenon that occurs at the junction interface, effectively forming a light-emitting region in the light-emitting layer, thereby improving efficiency and lifetime.

[0298] As in Examples 23 to 26 in Table 10, when hydrogen in a molecule is replaced with deuterium, it was confirmed that the kinetic energy of the hydrogen atom is reduced due to the increase in the molecular weight of the hydrogen atom, and molecular stability is increased, resulting in increased efficiency and lifetime.

[0299] <Experimental Example 2-1> - Fabrication of organic light-emitting device 1) Manufacturing of organic light-emitting devices A glass substrate coated with a 1,500Å thick indium tin oxide (ITO) thin film was ultrasonically cleaned in distilled water. After the distilled water cleaning, the substrate was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UVO (Ultraviolet Ozone) for 5 minutes in a UV (Ultraviolet) cleaning machine. The substrate was then transferred to a plasma cleaning machine (PT) and plasma treated in a vacuum to determine the work function of the ITO and remove any remaining film, before being transferred to a thermal evaporation system for organic deposition.

[0300] On the ITO transparent electrode (anode), a common layer consisting of a hole injection layer 2-TNATA (4,4',4"-Tris[2-naphthyl(phenyl)amino]triphenylamine) and a hole transport layer NPB (N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine) was formed.

[0301] An emitting layer was then formed thereon by thermal vacuum deposition as follows. Specifically, the compounds listed in Examples 1 to 26 in Table 11 below were used as the red host for the emitting layer, and the red phosphorescent dopant (piq)2(Ir)(acac) was doped into the red host at 3 wt% to form an emitting layer with a thickness of 500 Å. Then, bathocuproine (hereinafter referred to as 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.

[0302] Finally, lithium fluoride (LiF) was deposited on the electron transport layer to a thickness of 10 Å to form an electron injection layer, and then an aluminum (Al) cathode was deposited on the electron injection layer to a thickness of 1,200 Å to form a cathode, thereby completing the manufacture of an organic light emitting device.

[0303] 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.

[0304] 2) Driving voltage and luminous efficiency of organic light-emitting devices The electroluminescence (EL) characteristics of the organic light-emitting devices of Examples 1 to 26 in Table 11 thus manufactured were measured using a Mac Science M7000. Based on the measurement results, a reference luminance of 6,000 cd / m was measured using a Mac Science M6000 lifespan measurement device. 2 At that time, T 90 The T 90 means the lifespan (unit: h) until the brightness becomes 90% of the initial brightness.

[0305] The measured characteristics of the organic light emitting device are shown in Table 11 below.

[0306] [Table 11] Table 11 shows the case where the heterocyclic compound of Chemical Formula 1 and the heterocyclic compound of Chemical Formula 2 are simultaneously contained in the organic material layer of the organic light emitting device. As mentioned above, it is expected that the exciplex phenomenon will occur when the two compounds are simultaneously contained.

[0307] In addition, the heterocyclic compound of Formula 2 acts as an electron blocking layer (EBL) based on its high LUMO level, helping excited electrons to remain in the light-emitting layer region and creating an effective light-emitting region, which has been confirmed to significantly improve efficiency and lifetime. [Explanation of symbols]

[0308] 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. Heterocyclic compounds represented by one of the following chemical formulas 3 to 6: 【Chemistry 1】 【Chemistry 2】 【Transformation 3】 【Chemistry 4】 In the above Chemical Formulas 3 to 6, N-Het is a substituted or unsubstituted triazine group; a substituted or unsubstituted pyrimidine group; a substituted or unsubstituted quinazoline group; a substituted or unsubstituted quinoline group; a substituted or unsubstituted quinoxaline group; a substituted or unsubstituted benzofuro[3,2-d]pyrimidine group; a substituted or unsubstituted benzofuro[2,3-d]pyrimidine group; a substituted or unsubstituted benzo[4,5]thieno[3,2-d]pyrimidine group; or a substituted or unsubstituted benzo[4,5]thieno[2,3-d]pyrimidine group; L is a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group; a is an integer of 1 to 3, and when a is 2 or more, Ls are the same or different; R5 and R6 are hydrogen or deuterium; b is an integer of 0 to 2, c is an integer of 0 to 4, when b is 2, R5's are the same or different from each other, when c is 2 or more, R6's are the same or different from each other, The aforementioned 【Transformation 5】 is represented by any one of the following chemical formulas 1-1 to 1-6: 【Transformation 6】 【Transformation 7】 【Transformation 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 In the chemical formulas 1-1 to 1-6, R11 to R14 are the same or different and are each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl 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 benzene ring; R15 to R18 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; Rb is hydrogen; deuterium; or a substituted or unsubstituted C6 to C60 aryl group, m is an integer of 0 to 4, and when m is 2 or more, the Rb's are the same or different; When R11 to R15, R18, and Rb in Formula 1-2 are all hydrogen atoms, or when two adjacent groups among R11 to R14 in Formula 1-2 are bonded to each other to form an unsubstituted benzene ring, N-Het is a substituted or unsubstituted pyrimidine group; a substituted or unsubstituted quinazoline group; a substituted or unsubstituted quinoline group; a substituted or unsubstituted quinoxaline group; a substituted or unsubstituted benzofuro[3,2-d]pyrimidine group; a substituted or unsubstituted benzofuro[2,3-d]pyrimidine group; a substituted or unsubstituted benzo[4,5]thieno[3,2-d]pyrimidine group; or a substituted or unsubstituted benzo[4,5]thieno[2,3-d]pyrimidine group, In Chemical Formula 1-1 and Chemical Formula 1-3, when R12 and R13 are bonded to each other to form an unsubstituted benzene ring, at least one of R11, R14, R15 to R18, and Rb in Chemical Formula 1-1 and Chemical Formula 1-3 is selected from the group consisting of deuterium; a substituted or unsubstituted C6 to C60 aryl group; and a substituted or unsubstituted C2 to C60 heteroaryl group.

2. The heterocyclic compound according to claim 1, wherein R11 to R15, R18, and Rb in Chemical Formula 1-2 are all hydrogen atoms, or when two adjacent groups among R11 to R14 in Chemical Formula 1-2 are bonded to each other to form an unsubstituted benzene ring, the deuterium content in Chemical Formulas 3 to 6 is 10% or more and 100% or less, or L in Chemical Formulas 3 to 6 is a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group.

3. The heterocyclic compound according to claim 1, wherein one of the chemical formulas 3 to 6 is represented by any one of the following compounds: 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 [Chemistry 18] 【Chemistry 19】 【Chemistry 20】 【Chemistry 21】 【Chemistry 22】 【Chemistry 23】 【Chemistry 24】 【Chemistry 25】 。

4. 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 comprises one or more heterocyclic compounds according to any one of claims 1 to 3.

5. The organic light-emitting element according to claim 4 , wherein the organic material layer includes a light-emitting layer, and the light-emitting layer includes the heterocyclic compound.

6. The organic light-emitting device according to claim 4 , wherein the organic material layer includes a light-emitting layer, the light-emitting layer includes a host material, and the host material includes the heterocyclic compound.

7. The organic light-emitting device according to claim 4 , wherein the organic layer includes an electron injection layer or an electron transport layer, and the electron injection layer or the electron transport layer includes the heterocyclic compound.

8. The organic light-emitting device according to claim 4 , wherein the organic material layer comprises an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer comprises the heterocyclic compound.

9. 5. The organic light-emitting device according to claim 4, 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.

10. The organic light-emitting device according to claim 4 , wherein the organic material layer further comprises a heterocyclic compound represented by the following Chemical Formula 2: 【Chemistry 26】 In the above Chemical Formula 2, Ar1 is hydrogen; deuterium; 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; R51 to R58 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, a substituted or unsubstituted phosphine oxide group, and a substituted or unsubstituted amine group, 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.

11. The organic light-emitting device according to claim 10, wherein the chemical formula 2 is represented by any one of the following chemical formulas 10 to 12: 【Chemistry 27】 【Chemistry 28】 【Chemistry 29】 In the above chemical formulas 10 to 12, R61 to R70 are the same or different and are each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; and a substituted or unsubstituted C2 to C60 heteroaryl group; R71 to R74 are the same or different and are each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl 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 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle; Ar2 and Ar3 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; A1 is O; S; NAr4; or CRdRe; Rd and Re are the same or different and each independently represent a substituted or unsubstituted C1 to C60 alkyl group; or a substituted or unsubstituted C6 to C60 aryl group; Ar4 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; h and i are integers from 0 to 3; j is an integer from 0 to 2.

12. The organic light-emitting device according to claim 10, wherein the heterocyclic compound represented by Chemical Formula 2 is any one of the following compounds: 【Transformation 30】 【Chemistry 31】 。

13. A composition for an organic layer of an organic light-emitting device, comprising the heterocyclic compound represented by one of Chemical Formulas 3 to 6 according to any one of Claims 1 to 3 and a heterocyclic compound represented by Chemical Formula 2 below: 【Chemistry 32】 In the above Chemical Formula 2, Ar1 is 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; R51 to R58 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, a substituted or unsubstituted phosphine oxide group, and a substituted or unsubstituted amine group, 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.

14. 14. The composition for an organic material layer of an organic light-emitting device according to claim 13, wherein a weight ratio of the heterocyclic compound represented by one of Chemical Formulas 3 to 6 to the heterocyclic compound represented by Chemical Formula 2 in the composition is 1:10 to 10:

1.

15. providing a substrate; forming a first electrode on the substrate; forming one or more organic layers on the first electrode; forming a second electrode on the organic layer; The method for manufacturing an organic light-emitting device, wherein the step of forming an organic material layer comprises forming one or more organic material layers using the composition for an organic material layer according to claim 13 .

16. 16. The method of claim 15, wherein the forming of the organic material layer comprises pre-mixing the heterocyclic compound of one of Chemical Formulas 3 to 6 and the heterocyclic compound of Chemical Formula 2 and forming the organic material layer using a thermal vacuum deposition method.

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