Heterocyclic compound, organic light-emitting element including the same, composition for organic material layer of organic light-emitting element, and method for manufacturing organic light-emitting element

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 same, a composition for an organic 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 having such a structure, electrons and holes injected from the two electrodes combine in the organic thin film to form pairs, and then disappear, emitting light. The organic thin film may be configured as a single layer or multiple layers as required.

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

[0006] In order 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] There is a need for research into organic light-emitting devices that contain compounds having chemical structures that can satisfy the requirements for materials that can be used in organic light-emitting devices, such as suitable energy levels, electrochemical stability, and thermal stability, and 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 same, 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; 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 are the same or different from each other; 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-C60 aryl group; and a substituted or unsubstituted C2-C60 heteroaryl group, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6-C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2-C60 heterocycle, d is an integer of 0 to 2, and when d is 2, two Ra are the same or different from each other, R1 to R6 are the same or different and each independently represent hydrogen; deuterium; a halogen; 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 a substituted or unsubstituted C6 to C60 heteroaryl group; a substituted or unsubstituted phosphine oxide group; a substituted or unsubstituted silyl 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, 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, and when c is 2 or more, R6's are the same or different from each other.

[0012] According to one embodiment of the present application, there is provided an organic light-emitting device including a first electrode, a second electrode facing the first electrode, and one or more organic layers between the first electrode and the second electrode, wherein at least one of the organic layers includes at least one heterocyclic compound represented by Chemical Formula 1.

[0013] Further, 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 are each independently selected from the group consisting of hydrogen; deuterium; a halogen; 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 groups adjacent to each other 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.

[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. Effect of the Invention

[0016] The compounds described herein can be used as organic layer materials of organic light-emitting devices. The compounds can play the role of hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, etc. in organic light-emitting devices. In particular, the compounds can be used as light-emitting layer materials of organic light-emitting devices. For example, the compounds can be used alone as light-emitting materials, and the two compounds can be used together as light-emitting materials and can be used as host materials for light-emitting layers.

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

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

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

[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 the carbon atom. However, deuterium ( 2 H, Deuterium) is an isotope of hydrogen, so 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", it can mean that all positions of the substituents are hydrogen or deuterium. In other words, in the case of deuterium, it is an isotope of hydrogen, and some of the 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 in a compound in a mixed state, in the case where deuterium is not explicitly excluded, such as when the deuterium content is 0% or the hydrogen content is 100%. In other words, when it is expressed as "substituent X is hydrogen", it can mean a state in which hydrogen and deuterium are mixed, in which deuterium is not excluded, 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 the total number of substituents.

[0027] That is, in one example, [ka] In the case where the total number of substituents that the phenyl group may have is 5 (T1 in the formula), of which the number of deuterium is 1 (T2 in the formula), the deuterium content of 20% in the phenyl group represented by the following structural formula may be expressed as 20%.

[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 five hydrogen atoms.

[0029] In this specification, 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-methyl-butyl group, a 1-ethyl-butyl 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 pent ... Examples of such alkyl groups include, but are not limited to, 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 the present 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 the present specification, the alkoxy group may be a straight chain, a branched chain, or a cyclic chain. The number of carbon atoms of the alkoxy group is not particularly limited, but it is preferably one having 1 to 20 carbon atoms. Specifically, it may be 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., but is not limited thereto.

[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 polycyclic group means a group in which the cycloalkyl group is directly linked or condensed with another cyclic group. Here, the other cyclic group may be a cycloalkyl group, but may also be other types of cyclic groups, such as a heterocycloalkyl group, an aryl group, or a heteroaryl group. The number of carbon atoms in the cycloalkyl group may be 3 to 60, specifically 3 to 40, 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 the present specification, the heterocycloalkyl group includes O, S, Se, N, or Si as a heteroatom, includes a monocyclic or polycyclic group having 2 to 60 carbon atoms, and may be additionally substituted with other substituents. Here, the polycyclic group means a group in which the heterocycloalkyl group is directly linked 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 the aryl group is directly linked or condensed with another ring group. Here, the other ring group may be an aryl group, but may also be other types of ring 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 of the aryl group may be 6 to 60, specifically 6 to 40, and more specifically 6 to 25. Specific examples of the aryl group include a phenyl group, a biphenyl group, a triphenyl group, a naphthyl group, an anthryl group, a chrysenyl group, a phenanthrenyl group, a perylenyl group, a fluoranthenyl group, a triphenylenyl group, a phenalenyl group, a pyrenyl group, a tetracenyl group, a pentacenyl group, a fluorenyl group, an indenyl group, an acenaphthylenyl group, a benzofluorenyl group, a spirobifluorenyl group, a 2,3-dihydro-1H-indenyl group, and condensed ring groups thereof, but are not limited to these.

[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 thereto.

[0039] [ka] In this specification, the heteroaryl group includes S, O, Se, N, or Si as a heteroatom, includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be additionally substituted with other substituents. Here, the polycyclic ring means a group in which the heteroaryl group is directly linked or condensed with another ring group. Here, the other ring group may be a heteroaryl group, but may also be other types of ring groups, such as a cycloalkyl group, a heterocycloalkyl group, an aryl group, etc. The number of carbon atoms of the heteroaryl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 25.Specific examples of the 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, benzocathyl 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 an alkyl group include, but are not limited to, an azinyl group, a phthalazinyl group, a naphthyridinyl group, a phenanthrolinyl group, a benzo[c][1,2,5]thiadiazolyl group, a 5,10-dihydrodibenzo[b,e][1,4]azasilinyl group, a pyrazolo[1,5-c]quinazolinyl group, a pyrido[1,2-b]indazolyl group, a pyrido[1,2-a]imidazo[1,2-e]indolinyl group, and a 5,11-dihydroindeno[1,2-b]carbazolyl group.

[0040] In the present specification, the amine group may be selected from the group consisting of a monoalkylamine group, a monoarylamine group, a monoheteroarylamine group, -NH2, a dialkylamine group, a diarylamine group, a diheteroarylamine group, an alkylarylamine group, an alkylheteroarylamine group, and an arylheteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, a dibiphenylamine group, an anthracenylamine group, a 9-methyl-anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a triphenylamine group, a biphenylnaphthylamine group, a phenylbiphenylamine group, a biphenylfluorenylamine group, a phenyltriphenylenylamine group, and a biphenyltriphenylenylamine group, but are not limited thereto.

[0041] In this specification, the arylene group means 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 each divalent groups. In addition, the heteroarylene group means 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 each divalent groups.

[0042] In the present specification, the phosphine oxide group is represented by -P(=O)R101R102, where R101 and R102 may be the same or different and each may independently be a substituent consisting of at least one of hydrogen, deuterium, a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a cycloalkyl group, an aryl group, and a heterocyclic group. Specific examples of the phosphine oxide group include, but are not limited to, a diphenylphosphine oxide group and a dinaphthylphosphine oxide group.

[0043] In this specification, a silyl group is a substituent that contains Si and is 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 may be independently a substituent consisting of at least one of hydrogen, deuterium, a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a cycloalkyl group, an aryl group, and a heterocyclic group. Specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.

[0044] In this specification, the term "adjacent" may refer 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 the ortho positions on a benzene ring and two substituents substituted on the same carbon atom on an aliphatic ring are interpreted as "adjacent" groups to each other.

[0045] The aliphatic or aromatic hydrocarbon ring or hetero ring capable of forming the adjacent group may have the structures exemplified as the above-mentioned cycloalkyl group, cycloheteroalkyl group, aryl group, and heteroaryl group, except that the ring or hetero ring is not a monovalent group.

[0046] In the present specification, the term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent, and the position of the substitution is not limited as long as it is a position at which a hydrogen atom is substituted, i.e., a position at which a substituent can be substituted, and when two or more substituents are substituted, the two or more substituents may be the same or different from each other.

[0047] In this specification, "substituted or unsubstituted" means that the group is substituted or unsubstituted with one or more substituents selected from the group consisting of C1 to C60 linear or branched alkyl; C2 to C60 linear or branched alkenyl; C2 to C60 linear or branched alkynyl; C3 to C60 monocyclic or polycyclic cycloalkyl; C2 to C60 monocyclic or polycyclic heterocycloalkyl; C6 to C60 monocyclic or polycyclic aryl; C2 to C60 monocyclic or polycyclic heteroaryl; -SiRR'R"; -P(=O)RR'; C1 to C20 alkylamine; C6 to C60 monocyclic or polycyclic arylamine; and C2 to C60 monocyclic or polycyclic heteroarylamine, or is substituted or unsubstituted with a substituent in which two or more substituents selected from the above-mentioned substituents are linked.

[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, the 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, the 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, the R, R' and R'' are the same or different and each independently represent an alkyl group having 1 to 20 carbon atoms; or an aryl group having 6 to 20 carbon atoms.

[0053] In still another embodiment, the R, R' and R'' are the same or different and each independently represent an alkyl group having 1 to 10 carbon atoms; or an aryl group having 6 to 10 carbon atoms.

[0054] In still another embodiment, the 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.

[0057] In one embodiment of the present application, the above-mentioned Chemical Formula 1 may be represented by one of the following Chemical Formulas 3 to 6.

[0058] [ka] [ka] [ka] [ka] In the above 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 above 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 lifetime characteristics and excellent efficiency and operation.

[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, provided that when m is 2 or greater, the Rbs are the same or different from each other.

[0062] In the above Chemical Formulas 1-1 to 1-6, [ka] means the position at which the group is linked to Chemical Formula 1.

[0063] In said 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 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 said Chemical Formula 1-1 and Chemical Formula 1-3 may be selected from the group consisting of deuterium; substituted or unsubstituted C1 to C60 alkyl groups; substituted or unsubstituted C6 to C60 aryl groups; and substituted or unsubstituted C2 to C60 heteroaryl groups.

[0064] In the above 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 C6 to C40 aromatic hydrocarbon ring, at least one of R11, R14, R15 to R18, and Rb in the above Chemical Formula 1-1 and Chemical Formula 1-3 may be selected from the group consisting of deuterium; substituted or unsubstituted C6 to C60 aryl groups; and substituted or unsubstituted C2 to C60 heteroaryl groups.

[0065] In the above 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 the above 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 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 the above 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-C60 monocyclic or polycyclic heterocycle containing one or more N.

[0070] In another embodiment, N-Het is a C2-C60 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-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 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, and is a C2-C30 monocyclic or polycyclic heterocycle containing one or more N.

[0073] In still another embodiment, N-Het 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, and is a C2-C30 monocyclic or polycyclic heterocycle containing one or more N.

[0074] In still another embodiment, N-Het 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, and is a C2-C30 monocyclic or polycyclic heterocycle containing 1 to 3 N atoms.

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

[0076] In yet 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, said 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 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 the group is linked 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 above 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 may 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 yet other embodiments, L may be a direct bond.

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

[0095] In one embodiment of the present application, when R11 to R15, R18 and Rb in the above chemical formula 1-2 are all hydrogen or two adjacent groups among R11 to R14 in the above 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 the above chemical formula 1 may be a substituted or unsubstituted C2 to C60 monocyclic or polycyclic heterocycle containing 1 to 2 N.

[0096] In another embodiment, when R11 to R15, R18 and Rb in the above Chemical Formula 1-2 are all hydrogen or two adjacent groups among R11 to R14 in the above 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 the above Chemical Formula 1 may be a substituted or unsubstituted C2 to C40 monocyclic or polycyclic heterocycle containing 1 to 2 N.

[0097] In still another embodiment, when R11 to R15, R18 and Rb in the above chemical formula 1-2 are all hydrogen or two adjacent groups among R11 to R14 in the above 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 the above chemical formula 1 may be a substituted or unsubstituted C2 to C20 monocyclic or polycyclic heterocycle containing 1 to 2 N.

[0098] In still another embodiment, when R11 to R15, R18 and Rb in the above Chemical Formula 1-2 are all hydrogen or two adjacent groups among R11 to R14 in the above 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 the above 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 1 to 2 N.

[0099] In still another embodiment, when R11 to R15, R18 and Rb in the above Chemical Formula 1-2 are all hydrogen or two adjacent groups among R11 to R14 in the above 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 the above 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; 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 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 the above chemical formula 1-2 are all hydrogen or two adjacent groups among R11 to R14 in the above 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 the above 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 the above chemical formula 1-2 are all hydrogen or two adjacent groups among R11 to R14 in the above 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 the above 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 substitution among the positions serving as substituents in Chemical Formula 1. That is, if there are a total of 40 positions in Chemical Formula 1 that may be substituted with a substituent and 20 of these 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 the above chemical formula 1-2 are all hydrogen or two adjacent groups among R11 to R14 in the above 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 the above 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 the above Chemical Formula 1-2 are all hydrogen or two adjacent groups among R11 to R14 in the above 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 the above 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 the above chemical formula 1-2 are all hydrogen or two adjacent groups among R11 to R14 in the above 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 the above 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 the above chemical formula 1-2 are all hydrogen or two adjacent groups among R11 to R14 in the above 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 the above 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 the above chemical formula 1-2 are all hydrogen or two adjacent groups among R11 to R14 in the above 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 the above chemical formula 1 may be a C6 to C20 arylene group.

[0110] In still another embodiment, when R11 to R15, R18 and Rb in the above chemical formula 1-2 are all hydrogen or two adjacent groups among R11 to R14 in the above 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 the above chemical formula 1 may be a phenylene group.

[0111] In one embodiment of the present application, when R11 to R15, R18 and Rb in the chemical formula 1-2 are all hydrogen, or two adjacent groups among R11 to R14 in the 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 the chemical formula 1 may be a substituted or unsubstituted C2 to C60 monocyclic or polycyclic heterocycle containing 1 to 2 N, the deuterium content in the chemical formula 1 may be 10% or more and 100% or less, or L in the 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 may be a substituted or unsubstituted C6-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 another embodiment, 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-C40 monocyclic or polycyclic aryl group, or two or more adjacent groups may be bonded to each other to form a C6-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 groups adjacent to each other 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 monocyclic or polycyclic C6 to C20 aryl groups, 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. In this case, the heterocyclic compound of Chemical Formula 1 may be substituted with deuterium by 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 monocyclic or polycyclic C6 to C20 aryl groups, 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 be hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[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 each independently represent hydrogen; deuterium; a C6 to C40 aryl group; or a C2 to C40 heteroaryl group.

[0145] In still other embodiments, R15 to R18 may be the same or different and each independently represent 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 may 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 be hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[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 be hydrogen; deuterium; a C6 to C60 aryl group unsubstituted or substituted with 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 are the same or different and may each independently be 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] TIFF2025000803000027.tif126165 TIFF2025000803000028.tif231165 TIFF2025000803000029.tif149165 TIFF2025000803000030.tif219165 TIFF2025000803000031.tif129165 TIFF2025000803000032.tif218165 TIFF2025000803000033.tif121165 TIFF2025000803000034.tif219165 TIFF2025000803000035.tif219165 TIFF2025000803000036.tif218165 TIFF2025000803000037.tif168165 TIFF2025000803000038.tif204165 TIFF2025000803000039.tif128165 TIFF2025000803000040.tif163165 TIFF2025000803000041.tif254165 In addition, it is possible to synthesize compounds having the inherent properties of the introduced substituents by introducing various substituents into the structure of Chemical Formula 1. For example, it is possible to synthesize materials that satisfy the requirements of each organic layer by introducing into the core structure substituents that are mainly 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.

[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, and the applications of the material can be diversified.

[0163] In addition, in 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.

[0164] In another embodiment, an organic light-emitting device is provided that includes a first electrode, a second electrode facing the first electrode, and one or more organic layers between the first electrode and the second electrode, wherein at least one of the organic layers includes 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 layers provided between the first electrode and the second electrode, wherein at least one of the organic layers comprises two heterocyclic compounds represented by Chemical Formula 1.

[0166] In the organic light-emitting device, when two or more heterocyclic compounds are contained, 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 of 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 typical manufacturing method and materials for an organic light-emitting device, except that one or more organic layers are formed using the above-mentioned heterocyclic compound.

[0174] In the manufacture of an organic light emitting device, the heterocyclic compound is formed in an organic layer by a solution coating method as well as a vacuum deposition method, where the solution coating method refers to, but is not limited to, spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc.

[0175] The organic layer of the organic light-emitting device of the present invention may have a single-layer structure, or may have a multi-layer structure in which two or more organic layers are laminated. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as the organic layer. However, the structure of the organic light-emitting device is not limited thereto, and may include a smaller number of organic layers.

[0176] In the organic light-emitting device of the present invention, the organic 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 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 including 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 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 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 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 layer, and an anode are sequentially stacked on a substrate as shown in FIG.

[0184] Fig. 3 illustrates an example in which the organic layer is multi-layered. The organic light-emitting device in Fig. 3 includes a hole injection layer 301, a hole transport layer 302, an emission 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 laminated structure, and the remaining layers except for the emission layer may be omitted as necessary, 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 necessary.

[0186] In the organic light emitting device according to an 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 are each independently selected from the group consisting of hydrogen; deuterium; a halogen; 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 groups adjacent to each other 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.

[0188] In particular, an exciplex phenomenon occurs when the heterocyclic compound of Formula 2 is further included. 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 explaining the exciplex phenomenon. When the exciplex phenomenon occurs as shown in Figure 4, new S1 and T1 energy levels are formed, and the change in the red-shifted PL can be confirmed 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 the acceptor, and at this time, the light emitted at this energy level is red-shifted more than the light emitted by the donor and the acceptor, and PL is measured to confirm this. Therefore, by comparing the emission wavelength of a single host and the emission wavelength of a mixed host from the PL data, it can be confirmed whether an exciplex has been formed in this molecule.

[0191] When this exciplex phenomenon occurs between two molecules, 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 heterocyclic compound of Formula 2, donor (p-host), which has good hole transport ability, an exciplex can be formed, which shows a change in red-shifted PL, thereby helping to improve the light-emitting properties. In addition, the compound (donor (p-host)) corresponding to Formula 2 of the present application, which has good hole transport ability, is injected, and the life span can be significantly improved by the appropriate movement of the light-emitting zone in the light-emitting layer.

[0193] In one embodiment of the present application, the above-mentioned 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 represents 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 represents 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 formula 10 may be represented by the following 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.

[0197] In one embodiment of the present application, the above formula 11 may be represented by the following 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 above-mentioned 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 above Chemical Formulas 12-1 to 12-4, The definitions of Ar2 and A1 are the same as those in Chemical Formula 12. 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 C10 or less aryl group.

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

[0202] In another embodiment, Ar2 to Ar4 are the same or different and may each independently be 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 groups adjacent to each other 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 an aromatic hydrocarbon ring of C6 to C40.

[0210] In still another embodiment, R71 to R74 are the same or different and each independently represent hydrogen or deuterium, or two or more groups adjacent to each other 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 may independently 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 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 each independently be an alkyl group of C1 to C40.

[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 may independently 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 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 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 may be an aryl group having from C10 to C40, substituted or unsubstituted with a C1 to C20 alkyl group; or a C2 to C40 heteroaryl group, substituted or unsubstituted with one or more substituents selected from the group consisting of a C6 to C40 aryl group and a C2 to C40 heteroaryl group.

[0219] In still another embodiment, R81 and R82 may be represented by the following 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 from 0 to 3.

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

[0222] In another embodiment, said R83 is an aryl group 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 groups adjacent to each other may be bonded to each other to form a benzene ring.

[0226] In one embodiment of the present application, R96 to R98 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.

[0227] In another embodiment, R96 to R98 may be the same or different and each independently represent a C6 to C40 aryl group substituted or unsubstituted with one or more substituents selected from the group consisting of hydrogen; deuterium; a C1 to C20 alkyl group; 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] JPEG2025000803000056.jpg77165 In the organic light emitting device according to an embodiment of the present application, the compound represented by Chemical Formula 2 may be included 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 represented by 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 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.

[0235] In one embodiment of the present application, there is provided a method for manufacturing an organic light-emitting device, in which the step of forming the organic layer comprises pre-mixing the heterocyclic compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 and forming the pre-mixed organic 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 the 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. However, these are merely examples and are not intended to limit the scope of the present application. They may be replaced with materials known in the art.

[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 SnO2: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 having 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 materials with multilayer structures such as LiF / Al or LiO2 / Al.

[0241] As the hole injection material, a known hole injection material can be used, for example, a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Pat. No. 4,356,429, or a starburst type amine derivative described in the literature [Advanced Material, 6, p. 677 (1994)], for example, 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), a soluble conductive polymer polyaniline / dodecylbenzenesulfonic acid (Polyaniline / Dodecylbenzenesulfonic acid), etc. Poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate), Polyaniline / Camphor sulfonic acid, or Polyaniline / Poly(4-styrenesulfonate) 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 weight materials may also be used.

[0243] As the electron transport material, 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, metal complexes of 8-hydroxyquinoline and its derivatives, and the like can be used, and not only low molecular weight substances but also high molecular weight substances can 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 if necessary, two or more light-emitting materials may be mixed and used. In this case, two or more light-emitting materials may be deposited as individual supply sources or may be premixed and deposited as one supply 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 are involved in light emission may be used.

[0246] When the hosts of the light-emitting materials are mixed, the same type of hosts may be mixed and used, or different types of hosts may be mixed and used. For example, two or more types 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 one 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 an embodiment of the present application can also function in organic electronic devices, including organic solar cells, organic photoreceptors, organic transistors, etc., based on a similar principle to that applied to organic light-emitting devices. EXAMPLES

[0249] The present invention will be described in more detail with reference to the following examples, which are merely for 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 1-5 200.0g (596.4mmol) of 1-bromo-5-chloro-3-fluoro-2-iodobenzene, 82.4g (542.2mmol) of (2-methoxyphenyl)boronic acid, 31.3g (27.1mmol) of Pd(PPh)4, and 150.0g (1084.4mmol) of K2CO3 were dissolved in 1L / 200mL of 1,4-dioxane / H2O and refluxed for 24 hours. After the reaction was completed, the mixture was extracted with distilled water and dichloromethane (DCM) at room temperature, and 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=1:10) to obtain 137 g (80%) of the target compound 1-5.

[0252] 2) Preparation of Compound 1-4 Compound 1-5 (82g, 259.8mmol) and BBr3 (49mL, 519.7mol) were dissolved in DCM (800mL) and refluxed for 1 hour. After the reaction was completed, the mixture was extracted with distilled water and DCM at room temperature, and the organic layer was dried with MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:1) to obtain the target compound 1-4 (65.3g, 83%).

[0253] 3) Preparation of Compound 1-3 Compound 1-4 (65.3g, 216.5mM) and K2CO3 (59.9g, 433.1mmol) were dissolved in dimethylformamide (DMF) (300mL) and refluxed for 4 hours. After the reaction was completed, the mixture was extracted with distilled water and DCM at room temperature, and the organic layer was dried with MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:5) and recrystallized from methanol to obtain the target compound 1-3 (54.8g, 90%).

[0254] 4) Preparation of Compound 1-2 Compound 1-3 (20.0g, 70mmol), bis(pinacolato)diboron (23g, 92mmol), Pd(dppf)Cl2 (2.6g, 3.55mmol), and KOAc (20.9g, 213mmol) were dissolved in 1,4-dioxane (350mL) and refluxed for 2 hours. After the reaction was completed, the mixture was extracted with distilled water and DCM at room temperature, and the organic layer was dried with MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified on silica and recrystallized with hexane to obtain the target compound 1-2 (20.7g, 89%).

[0255] 5) Preparation of Compound 1-1 Compound 1-2 10.7g (32.6mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine 8.7g (32.6mmol), Pd(PPh)4 1.88g (1.63mmol), K2CO3 13.5g (98mmol) were dissolved in 1,4-dioxane / H2O160 / 30mL and refluxed for 6 hours. After the reaction was completed, the solid was filtered and washed with dioxane / distilled water / acetone to obtain the target compound 1-1 12.4g (88%).

[0256] 6) Preparation of Compound 1 Compound 1-1 6g (13.8mmol), 5H-benzo[b]carbazole 3g (13.8mmol), Pd2(dba) 31.2g (1.38mmol), Xphos 1.3g (2.8mmol), NaPtBu 4g (41.4mmol) were dissolved in xylene 70mL and refluxed for 12 hours. After the reaction was completed, the solid was filtered, washed with distilled water and dried. The dried solid was dissolved in DCB by boiling and purified with silica, and the solvent was removed by rotary evaporator. Recrystallization with acetone gave the target compound 1 7.8g (86%).

[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 in Production Example 1.

[0258] [Table 1] JPEG2025000803000059.jpg204165 JPEG2025000803000060.jpg218165 JPEG2025000803000061.jpg198165 JPEG2025000803000062.jpg186165 JPEG2025000803000063.jpg219165 JPEG2025000803000064.jpg220165 JPEG2025000803000065.jpg105165

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

[0260] 1) Preparation of Compound 21-2 Compound 21-3 11.0g (39.1mmol), 5H-benzo[b]carbazole 8.49g (39.1mmol), CuI 7.44g (39.1mmol), trans-1,2-cyclohexanediamine 4.46g (39.1mmol), K3PO4 16.59g (78.14mM) were dissolved in xylene 200mL and refluxed for 24 hours. After the reaction was completed, it was extracted with distilled water and DCM at room temperature, and the organic layer was dried with MgSO4 and the solvent was removed with a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:4) and recrystallized with methanol to obtain the target compound 21-2 12.4g (76%).

[0261] 2) Preparation of Compound 21-1 Compound 21-2 12.4g (29.7mmol), bis(pinacolato)diboron 8.29g (32.64mmol), Pd2(dba) 31.36g (1.48mmol), PCy 31.25g (4.45mmol), KOAc 5.82g (59.3mM) were dissolved in 1,4-dioxane 200mL and refluxed for 4 hours. After the reaction was completed, it was extracted with distilled water and DCM at room temperature, the organic layer was dried with MgSO4, and the solvent was removed with a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:3) and recrystallized with methanol to obtain the target compound 21-1 13.5g (89%).

[0262] 3) Preparation of Compound 21 Compound 21-1 (13.5g, 26.4mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (7.8g, 29.0mM), Pd(PPh) (41.53g, 1.3mmol), and K2CO3 (7.33g, 53.0mM) were dissolved in 1,4-dioxane / H2O (150 / 30mL) and refluxed for 4 hours. After the reaction was completed, the resulting solid was washed with distilled water and acetone and dried. The dried solid was dissolved in DCB by boiling and purified with silica, and the solvent was removed by rotary evaporator. Recrystallization from methanol gave the target compound 21 (13.4g, 82%).

[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] JPEG2025000803000068.jpg207165 JPEG2025000803000069.jpg126165

[0265] <Production Example 3> Production of Compound 51 [ka] The compound was synthesized 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 Preparation Example 3, except that Intermediate A and Intermediate B in Table 3 below were used.

[0267] [Table 3] JPEG2025000803000072.jpg214165 JPEG2025000803000073.jpg208165 JPEG2025000803000074.jpg210165 JPEG2025000803000075.jpg193165 JPEG2025000803000076.jpg209165 JPEG2025000803000077.jpg102165

[0268] <Production Example 4> Production of Compound 76 [ka] The compound was synthesized 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 in Production Example 2.

[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] JPEG2025000803000080.jpg193165 JPEG2025000803000081.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 produced in the same manner as in the above-mentioned Preparation Examples.

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

[0272] [Table 5] TIFF2025000803000083.tif253165 TIFF2025000803000084.tif253165 TIFF2025000803000085.tif75165 [Table 6] TIFF2025000803000087.tif255165 TIFF2025000803000088.tif254165 TIFF2025000803000089.tif251165 TIFF2025000803000090.tif114165

[0273] <Example> 1) Preparation of organic light-emitting device (red host) A glass substrate coated with a thin film of indium tin oxide (ITO) to a thickness of 1,500 Å was ultrasonically cleaned with distilled water. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UVO for 5 minutes using UV in a UV cleaner. The substrate was then transferred to a plasma cleaner (PT) and plasma treated in a vacuum state to determine the work function of the ITO and remove residual film, before being transferred to a thermal evaporation device for organic deposition.

[0274] A common layer, 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), were formed on the ITO transparent electrode (anode).

[0275] An emitting layer was formed thereon by thermal vacuum deposition as follows: The emitting layer was formed by doping the host with 3% (piq)2(Ir)(acac) by weight using the compound shown in Table 8 below as the host and (piq)2(Ir)(acac) as the red phosphorescent dopant, and was deposited to a thickness of 500 Å. Then, 60 Å of BCP was deposited as a hole blocking layer, and 200 Å of Alq3 was deposited thereon as an electron transport 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 the production of 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 electroluminescence device fabricated as described above were measured using a Mac Science M7000. Based on the measurement results, a reference luminance of 6,000 cd / m was determined using a Mac Science M6000 lifetime 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 compound and the example compound can be seen from Table 7. The results show that the heterocyclic compound of the present application, which is represented by Chemical Formula 1, has a larger conjugation effect as the benzene ring of the carbazole is extended (condensed), and has a smaller band gap and smaller T1 level than the comparative compounds A to F, making it suitable as a red host for an organic light-emitting device.

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

[0281] [Table 8] TIFF2025000803000094.tif213165 As can be seen from Table 8, when the compound of Formula 1 is included in the organic layer of the organic light emitting device, it can be confirmed that the driving voltage, efficiency and lifetime are significantly improved. This result is because the bipolar nature of having a donor with good hole transport ability and an acceptor with good electron transport ability in one molecule can efficiently transport electrons and holes, which helps to improve the light emitting characteristics. In addition, it can be confirmed that the HOMO level is controlled by extending a benzene ring to the donor with good hole transport ability, minimizing the trap phenomenon occurring at the contact interface, and the light emitting zone in the light emitting layer is effectively formed, improving the lifetime.

[0282] [Table 9] TIFF2025000803000096.tif164165 It can be seen from Table 9 that the driving voltage, efficiency and lifespan 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 an exciplex phenomenon occurs when the two compounds are simultaneously contained.

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

[0284] Figure 4 is a diagram explaining the exciplex phenomenon. When the exciplex phenomenon occurs as shown in Figure 4, new S1 and T1 energy levels are formed, and the change in the red-shifted PL can be confirmed 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 the case where a single host was used.

[0287] When the exciplex phenomenon between two molecules occurs, Reverse Intersystem Crossing (RISC) occurs, which can increase the internal quantum efficiency to 100%. As a result, it was confirmed that the mixed host has the advantage of increasing the internal quantum efficiency through the formation of exciplexes compared to a single host.

[0288] In particular, the compound of Formula 1 is a bipolar compound that does not have a 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 the light-emitting characteristics. 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 thin film of indium tin oxide (ITO) to a thickness of 1,500 Å was ultrasonically cleaned with distilled water. After the distilled water cleaning was completed, 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 using UV in a UV (Ultraviolet) cleaning machine. The substrate was then transferred to a plasma cleaning machine (PT) and plasma treated in a vacuum state to determine the work function of the ITO and remove residual film, before being transferred to a thermal evaporation device for organic deposition.

[0290] A common layer, 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), were formed on the ITO transparent electrode (anode).

[0291] An emitting layer was formed thereon by thermal vacuum deposition as follows. Specifically, the compounds shown in Examples 1 to 26 in Table 10 below were used as the red host of the emitting layer, and the red host was doped with 3 wt% of a red phosphorescent dopant (piq)2(Ir)(acac) to deposit an emitting layer having a thickness of 500 Å. Thereafter, 60 Å of bathocuproine (hereinafter, BCP) was deposited as a hole blocking layer, and 200 Å of Alq3 was deposited thereon as an electron transport 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 the production of 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 M7000 manufactured by Mac Science Co., Ltd., and the measurement results were used to measure the reference luminance of 6,000 cd / m2 or less using a lifetime measuring device (M6000) manufactured by Mac Science Co., Ltd. 2 At the time, T 90 The above T 90 means the time it takes for the brightness to reach 90% of the initial brightness (unit: h).

[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 layer of the organic light emitting device, it can be confirmed that the driving voltage, efficiency and lifetime are improved. As in Examples 1 to 11, weakening the acceptor involved in the electron transport ability can help to adjust the HOMO&LUMO levels and form an appropriate threshold voltage. In addition, it can be confirmed that adjusting the acceptor characteristics 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 efficiency and lifespan are improved by minimizing the trap phenomenon occurring at the junction interface by controlling the HOMO&LUMO levels and effectively forming a light-emitting region in the light-emitting layer.

[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 the molecular stability is increased, thereby increasing the efficiency and lifespan.

[0299] <Experimental Example 2-1> - Fabrication of organic light-emitting device 1) Manufacturing of organic light-emitting devices A glass substrate coated with a thin film of indium tin oxide (ITO) to a thickness of 1,500 Å was ultrasonically cleaned with distilled water. After the distilled water cleaning was completed, 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 using UV in a UV (Ultraviolet) cleaning machine. The substrate was then transferred to a plasma cleaning machine (PT) and plasma treated in a vacuum state to determine the work function of the ITO and remove residual film, before being transferred to a thermal evaporation device for organic deposition.

[0300] A common layer, 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), were formed on the ITO transparent electrode (anode).

[0301] An emitting layer was formed thereon by thermal vacuum deposition as follows. Specifically, a compound shown in Examples 1 to 26 in Table 11 below was used as the red host of the emitting layer, and a red phosphorescent dopant (piq)2(Ir)(acac) was doped into the red host at 3 wt % to deposit an emitting layer having a thickness of 500 Å. Thereafter, bathocuproine (hereinafter, 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 transport layer thereon.

[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 the production of 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 M7000 manufactured by Mac Science, and the measurement results were used to measure whether the reference luminance was 6,000 cd / m or less using a lifetime measuring device (M6000) manufactured by Mac Science. 2 At the time, T 90 The above T 90 means the time it takes for the brightness to reach 90% of the initial brightness (unit: h).

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

[0306] [Table 11] Table 11 shows that when the heterocyclic compound of Formula 1 and the heterocyclic compound of Formula 2 are simultaneously contained in an organic material layer of an organic light emitting device, as mentioned above, it is expected that an 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 a 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 lifespan. [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. A heterocyclic compound represented by the following chemical formula 1: 【Chemistry 45】 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; 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 are the same or different from each other; 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-C60 aryl group; and a substituted or unsubstituted C2-C60 heteroaryl group; or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6-C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2-C60 heterocycle; d is an integer of 0 to 2; when d is 2, two Ra are the same or different from each other; R1 to R6 are the same or different and each independently represent hydrogen; deuterium; a halogen; 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 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, R5's are the same or different from each other, and when c is 2 or more, R6's are the same or different from each other.

2. The heterocyclic compound according to claim 1, wherein the chemical formula 1 is represented by one of the following chemical formulas 3 to 6: 【Chemistry 46】 【Chemistry 47】 【Chemistry 48】 【Chemistry 49】 In the 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 formula 1.

3. The above 【Chemistry 50】 The heterocyclic compound according to claim 1, which is represented by any one of the following chemical formulas 1-1 to 1-6: 【Chemistry 51】 【Chemistry 52】 【Chemistry 53】 【Chemical 54】 【Chemistry 55】 【Chemistry 56】 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 represents 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 Rbs are the same or different.

4. The heterocyclic compound according to claim 3, wherein when R12 and R13 in Chemical Formula 1-1 and Chemical Formula 1-3 are bonded 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 is 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.

5. The heterocyclic compound according to claim 3, wherein R11 to R15, R18, and Rb in the formula 1-2 are all hydrogen, or when two adjacent groups among R11 to R14 in the 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 the formula 1 is a substituted or unsubstituted C2 to C60 monocyclic or polycyclic heterocyclic group containing 1 to 2 N, the deuterium content in the formula 1 is 10% or more and 100% or less, or L in the formula 1 is a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group.

6. The heterocyclic compound according to claim 1, wherein the N-Het is represented by the following chemical formula 2-1: 【Chemistry 57】 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.

7. The heterocyclic compound according to claim 6, wherein the chemical formula 2-1 is any one of the following structural formulas: 【Chemistry 58】 In the above structural formula, The definitions of R21 to R25 are the same as those in Chemical Formula 2-1.

8. The heterocyclic compound according to claim 1 , wherein the chemical formula 1 is represented by any one of the following compounds: 【Chemistry 59】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】

9. An organic light-emitting device comprising a first electrode, a second electrode provided opposite to the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contain one or more heterocyclic compounds according to any one of claims 1 to 8.

10. The organic light-emitting element according to claim 9 , wherein the organic layer includes a light-emitting layer, and the light-emitting layer includes the heterocyclic compound.

11. The organic light-emitting device according to claim 9 , wherein the organic layer comprises a light-emitting layer, the light-emitting layer comprises a host material, and the host material comprises the heterocyclic compound.

12. The organic light-emitting device according to claim 9 , wherein the organic layer comprises an electron injection layer or an electron transport layer, and the electron injection layer or the electron transport layer comprises the heterocyclic compound.

13. The organic light-emitting device according to claim 9 , wherein the organic 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.

14. The organic light-emitting device according to claim 9 , further comprising 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.

15. The organic light-emitting device according to claim 9 , wherein the organic layer further comprises a heterocyclic compound represented by the following Chemical Formula 2: 【Chemistry 60】 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 are each independently selected from the group consisting of hydrogen; deuterium; a halogen; 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.

16. The organic light-emitting device according to claim 15, wherein the formula 2 is represented by any one of the following formulas 10 to 12: 【Chemistry 61】 【Chemistry 62】 【Chemistry 63】 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 represents a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; A1 is O; S; NAr4; or CRdRe; Rd and Re are the same or different, and each independently represents 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-C60 alkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group; h and i are integers from 0 to 3; j is an integer from 0 to 2.

17. The organic light-emitting device according to claim 15, wherein the heterocyclic compound represented by Chemical Formula 2 is any one of the following compounds: 【Chemistry 64】 【change】

18. A composition for an organic layer of an organic light-emitting device, comprising the heterocyclic compound represented by Chemical Formula 1 according to any one of Claims 1 to 8 and a heterocyclic compound represented by Chemical Formula 2 below: 【Chemistry 65】 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 are each independently selected from the group consisting of hydrogen; deuterium; a halogen; 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.

19. The composition for an organic material layer of an organic light-emitting device according to claim 18, wherein a weight ratio of the heterocyclic compound represented by Chemical Formula 1 to the heterocyclic compound represented by Chemical Formula 2 in the composition is 1:10 to 10:

1.

20. 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 layer comprises the step of forming one or more organic layers using the composition for an organic layer according to claim 18 .

21. 21. The method of claim 20, wherein the forming of the organic material layer comprises pre-mixing the heterocyclic compound of Chemical Formula 1 and the heterocyclic compound of Chemical Formula 2 and forming the organic material layer using a thermal vacuum deposition method.

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