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

Abstract

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

Description

[Technical Field]

[0001] The present specification relates to a heterocyclic compound, an organic light-emitting device containing the same, a method for producing the same, and a composition for an organic layer. This specification claims the benefit of the filing date of Korean Patent Application No. 10-2020-0048060, filed with the Korean Intellectual Property Office on April 21, 2020, the entire contents of which are incorporated herein by reference. [Background technology]

[0002] Electroluminescent devices are a type of self-luminous display device, and have the advantages of a wide viewing angle, excellent contrast, and fast response speed. An organic light-emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to an organic light-emitting device with this structure, electrons and holes injected from the two electrodes combine in the organic thin film to form pairs and then disappear, emitting light. The organic thin film can be configured as a single layer or multiple layers as needed.

[0003] The organic thin film material may have a light-emitting function as needed. For example, the organic thin film material may be a compound that can form an emitting layer by itself, or a compound that can function as a host or dopant in a host-dopant emitting layer. In addition, the organic thin film material may be a compound that can perform functions such as hole injection, hole transport, electron blocking, hole blocking, electron transport, and electron injection. In order to improve the performance, lifetime or efficiency of organic light-emitting devices, there is a constant demand for development of materials for organic thin films. Summary of the Invention [Problem to be solved by the invention]

[0004] An object of the present invention is to provide a heterocyclic compound, an organic light-emitting device containing the heterocyclic compound, a method for producing the same, and a composition for an organic layer. [Means for solving the problem]

[0005] In one embodiment of the present application, there is provided a heterocyclic compound represented by the following Chemical Formula 1: [ka] In the above Chemical Formula 1, Ar1 to Ar4 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; L1 is a direct bond; a substituted or unsubstituted C6-C60 arylene group; or a substituted or unsubstituted C2-C60 heteroarylene group; Z1 is selected from the group consisting of halogen; -CN; substituted or unsubstituted C1-C60 alkyl groups; substituted or unsubstituted C10-C60 aryl groups; substituted or unsubstituted C2-C60 heteroaryl groups containing O or S as a heteroatom; -P(=O)RR'; -SiRR'R''; and substituted or unsubstituted amine groups; When Z1 is a substituted or unsubstituted, bicyclic or tetracyclic C15 to C60 aryl group having 9 or less protons, L1 is a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, wherein R, R', and R'' are the same or different and each independently represent a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; a is an integer from 1 to 4, b is an integer from 1 to 6; When a and b are each 2 or more, the substituents in each bracket are the same or different. Furthermore, in one embodiment of the present application, there is provided an organic light-emitting device comprising: a first electrode; a second electrode provided opposite the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers contains a heterocyclic compound represented by Chemical Formula 1.

[0006] In addition, one embodiment of the present application provides an organic light-emitting device, wherein the organic material layer containing the heterocyclic compound of Chemical Formula 1 further contains a heterocyclic compound represented by Chemical Formula 2 below. [ka] In the above Chemical Formula 2, Rc and Rd are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, a halogen group, -CN, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C60 cycloalkyl group, a substituted or unsubstituted C2-C60 heterocycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C2-C60 heteroaryl group, -Si(R10)(R11)(R12); -P(=O)(R10)(R11); 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-C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2-C60 heterocycle; R10, R11, and R12 are the same or different and each independently represent hydrogen; deuterium; -CN; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group; Ra and Rb are the same or different and each independently represent a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; r and s are each an integer of 0 to 7, When r and s are each 2 or greater, the substituents in each bracket are the same or different.

[0007] Furthermore, another embodiment of the present application provides a composition for an organic material layer of an organic light-emitting device, comprising the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2.

[0008] Finally, one embodiment of the present application provides a method for manufacturing an organic light-emitting device, the method including the steps of: preparing a substrate; forming a first electrode on the substrate; forming one or more organic material layers on the first electrode; and forming a second electrode on the organic material layers, wherein the step of forming the organic material layers includes forming one or more organic material layers using a composition for an organic material layer according to one embodiment of the present application. [Effects of the Invention]

[0009] The compounds described herein may be used as organic layer materials in organic light-emitting devices. The compounds may serve as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, etc. In particular, the compounds may be used as light-emitting layer materials in organic light-emitting devices.

[0010] Specifically, the compound may be used alone as an emitting material, or may be used as a host material or dopant material in an emitting layer. When the compound represented by Chemical Formula 1 is used in an organic layer, the driving voltage of the device can be reduced, the light efficiency can be improved, and the life characteristics of the device can be improved due to the thermal stability of the compound.

[0011] In addition, the heterocyclic compound represented by Chemical Formula 1 has a -(L1)a-(Z1)b substituent, and thus the LUMO orbital is sufficiently long and decentralized from the triazine group, which is the core structure, to the -(L1)a-(Z1)b substituent, thereby effectively stabilizing electrons. As a result, an organic light-emitting device including the compound has excellent life characteristics.

[0012] In particular, the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2 may be simultaneously used as materials for the light-emitting layer of an organic light-emitting device, which can reduce the driving voltage of the device, improve light efficiency, and particularly improve the life characteristics of the device due to the thermal stability of the compound. [Brief explanation of the drawings]

[0013] [Figure 1] FIG. 1 is a diagram schematically illustrating a stacked structure of an organic light-emitting device according to an embodiment of the present application. [Figure 2] FIG. 2 is a diagram schematically illustrating a stacked structure of an organic light-emitting device according to an embodiment of the present application. [Figure 3] FIG. 3 is a diagram schematically illustrating a stacked structure of an organic light-emitting device according to an embodiment of the present application. DETAILED DESCRIPTION OF THE INVENTION

[0014] The present application will be described in detail below. As used herein, the term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position of the substitution is not limited as long as it is a position at which a hydrogen atom is substituted, i.e., a position at which a substituent can be substituted. When two or more substituents are substituted, the two or more substituents may be the same or different.

[0015] In this specification, the term "substituted or unsubstituted" means being substituted or unsubstituted with one or more substituents selected from the group consisting of C1 to C60 linear or branched alkyl; C2 to C60 linear or branched alkenyl; C2 to C60 linear or branched alkynyl; C3 to C60 monocyclic or polycyclic cycloalkyl; C2 to C60 monocyclic or polycyclic heterocycloalkyl; C6 to C60 monocyclic or polycyclic aryl; C2 to C60 monocyclic or polycyclic heteroaryl; -SiRR'R''; -P(=O)RR'; C1 to C20 alkylamine; C6 to C60 monocyclic or polycyclic arylamine; and C2 to C60 monocyclic or polycyclic heteroarylamine, or being substituted or unsubstituted with a substituent in which two or more substituents selected from the above-mentioned exemplary substituents are linked together, The R, R', and R'' may be the same or different, and each independently represent a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0016] In this specification, the term "substituted or unsubstituted" means substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium; halogen; cyano group; 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 substituted or unsubstituted with a substituent in which two or more substituents selected from the above-mentioned exemplary substituents are linked together,

[0017] The R, R', and R'' may be the same or different, and each independently represent a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0018] In this specification, the "proton number" means the number of substituents that a specific compound may have, and specifically, the proton number may mean the number of hydrogen atoms. For example, unsubstituted benzene can be represented by 5 protons, unsubstituted naphthyl group can be represented by 7 protons, naphthyl group substituted with phenyl group can be represented by 6 protons, and unsubstituted biphenyl group can be represented by 9 protons.

[0019] In this specification, "when no substituent is shown in the chemical formula or compound structure" means that a hydrogen atom is bonded to a carbon atom. However, deuterium ( 2 H, Deuterium) is an isotope of hydrogen, so some hydrogen atoms may be deuterium.

[0020] In one embodiment of the present application, "when no substituent is shown in a chemical formula or compound structure," may mean that all positions available for a substituent are hydrogen or deuterium. That is, deuterium is an isotope of hydrogen, and some hydrogen atoms may be deuterium, which is an isotope, and in this case, the deuterium content may be 0% to 100%.

[0021] In one embodiment of the present application, when "substituents are not shown in a chemical formula or compound structure," if the deuterium content is 0%, the hydrogen content is 100%, and all substituents are hydrogen, and deuterium is not explicitly excluded, hydrogen and deuterium may be used together in the compound.

[0022] In one embodiment of the present application, deuterium is one of the isotopes of hydrogen, and is an element having a deuteron consisting of one proton and one neutron as an atomic nucleus, and can be represented by hydrogen-2, and its atomic symbol is D or 2 It can also be written as H.

[0023] 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. In one embodiment of the present application, the content T% of a specific substituent can be defined as T2 / T1×100=T%, where T1 is the total number of substituents that the base compound may have and T2 is the number of specific substituents among them.

[0024] That is, in one example: [ka] In a phenyl group represented by the formula (I), the deuterium content of 20% can be expressed as 20% when the total number of substituents that the phenyl group can have is 5 (T1 in the formula), of which the number of deuterium is 1 (T2 in the formula). That is, a phenyl group with a deuterium content of 20% can be represented by the following structural formula: [ka]

[0025] In addition, in one embodiment of the present application, a "phenyl group with a deuterium content of 0%" may refer to a phenyl group that does not contain a deuterium atom, that is, a phenyl group that has 5 hydrogen atoms.

[0026] In this specification, the halogen may be fluorine, chlorine, bromine or iodine.

[0027] In this specification, the alkyl group includes a straight or branched chain having 1 to 60 carbon atoms, and may be further substituted with other substituents. The number of carbon atoms in the alkyl group may be 1 to 60, specifically 1 to 40, more specifically 1 to 20. Specific examples include a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a 1-methylbutyl group, a 1-ethylbutyl group, a pentyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a hexyl group, an n-hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a 3,3-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group, a hexyl group, a 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 hexyl ... Examples of such alkyl groups include, but are not limited to, ethyl, 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.

[0028] In this specification, the alkenyl group includes a C2-60 linear or branched chain and may be further substituted with other substituents. The number of carbon atoms in the alkenyl group may be 2-60, specifically 2-40, and more specifically 2-20. 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.

[0029] In this specification, the alkynyl group includes a C2 to C60 straight or branched chain, and may be further 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.

[0030] In this specification, the alkoxy group may be linear, branched, or cyclic. The number of carbon atoms in the alkoxy group is not particularly limited, but preferably has 1 to 20 carbon atoms. Specific examples include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, and p-methylbenzyloxy.

[0031] In this specification, the cycloalkyl group includes a monocyclic or polycyclic group having 3 to 60 carbon atoms and may be further substituted with other substituents. Here, polycyclic means a group in which 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.

[0032] In this specification, the heterocycloalkyl group contains O, S, Se, N, or Si as a heteroatom, includes a monocyclic or polycyclic group having 2 to 60 carbon atoms, and may be further substituted with other substituents. Here, polycyclic means a group in which the heterocycloalkyl group is directly linked to or condensed with another cyclic group. Here, the other cyclic group may be a heterocycloalkyl group, but may also be other types of cyclic groups, such as a cycloalkyl group, an aryl group, or a heteroaryl group. The number of carbon atoms in the heterocycloalkyl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 20.

[0033] In this specification, the aryl group includes a monocyclic or polycyclic ring having 6 to 60 carbon atoms, and may be further substituted with other substituents. Here, the polycyclic ring means a group in which an aryl group is directly linked to or condensed with another cyclic group. Here, the other cyclic group may be an aryl group, but may also be other types of cyclic groups, such as a cycloalkyl group, a heterocycloalkyl group, or a heteroaryl group. The aryl group includes a spiro group. The number of carbon atoms in the aryl group may be 6 to 60, specifically 6 to 40, more specifically 6 to 25. Specific examples of the aryl group include, but are not limited to, a phenyl group, a biphenyl group, a terphenyl group, a quarterphenyl group, a quinquephenyl group, a naphthyl group, an anthryl group, a chrysenyl group, a phenanthrenyl group, a ferrylenyl group, a fluoranthenyl group, a triphenylenyl group, a phenalenyl group, a pyrenyl group, a tetracenyl group, a pentacenyl group, a fluorenyl group, an indenyl group, an acenaphthylenyl group, a benzofluorenyl group, a spirobifluorenyl group, a 2,3-dihydro-1H-indenyl group, and fused ring groups thereof.

[0034] As used herein, a phosphine oxide group is —P(═O)R 101 R 102 and R 101 and R 102are the same or different and may each 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. Specifically, they may be substituted with an aryl group, and the aryl group may be one of the above-mentioned examples. For example, phosphine oxide groups include, but are not limited to, diphenylphosphine oxide and dinaphthylphosphine oxide.

[0035] As used herein, a silyl group is a substituent that contains Si and is directly linked to the Si atom as a radical, and is represented by -SiR 104 R 105 R 106 and R 104 ~R 106 are the same or different and may each independently represent at least one substituent selected from the group consisting of hydrogen, deuterium, a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a cycloalkyl group, an aryl group, and a heterocyclic group. Specific examples of silyl groups include, but are not limited to, trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl.

[0036] In this specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

[0037] When the fluorenyl group is substituted, [ka] It can be, but is not limited to, the following.

[0038] In this specification, the heteroaryl group contains S, O, Se, N, or Si as a heteroatom, includes a monocyclic or polycyclic group having 2 to 60 carbon atoms, and may be further substituted with other substituents. Here, the polycyclic group refers to a group in which the heteroaryl group is directly linked to or condensed with another cyclic group. Here, the other cyclic group may be a heteroaryl group, but may also be other types of cyclic groups, such as a cycloalkyl group, a heterocycloalkyl group, or an aryl group. The number of carbon atoms in the heteroaryl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 25.Specific examples of the heteroaryl group include a pyridyl group, a pyrrolyl group, a pyrimidyl group, a pyridazinyl group, a furanyl group, a thiophene group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, a furazanyl group, an oxadiazolyl group, a thiadiazolyl group, a dithiazolyl group, a tetrazolyl group, a pyranyl group, a thiopyranyl group, a diazinyl group, an oxazinyl group, a thiazinyl group, a dioxinyl group, a triazinyl group, a tetrazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, an isoquinazolinyl group, a quinozolinyl group, a naphthyridyl group, an acridinyl group, a phenanthridinyl group, an imidazopyridinyl group, a diazanaphthalenyl group, a triazaindene group, an indolyl group, an indolizinyl group, a benzothiazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiophene group, a benzofuran group, a dibenzothiophene group, a dibenzofuran group, a carbazolyl group, a benzo Carbazolyl group, dibenzocarbazolyl group, phenazinyl group, dibenzosilole group, spirobi(dibenzosilole), dihydrophenazinyl group, phenoxazinyl group, phenanthridyl group, imidazopyridinyl group, thienyl group, indolo[2,3-a]carbazolyl group, indolo[2,3-b]carbazolyl group, indolinyl group, 10,11-dihydro-dibenzo[b,f]azepine group, 9,10-dihydroacridinyl group, phenanthrazinyl group, phenothiazolyl group, Examples of such alkyl groups include, but are not limited to, thiazinyl, phthalazinyl, naphthyridinyl, phenanthrolinyl, benzo[c][1,2,5]thiadiazolyl, 5,10-dihydrodibenzo[b,e][1,4]azasilinyl, pyrazolo[1,5-c]quinazolinyl, pyrido[1,2-b]indazolyl, pyrido[1,2-a]imidazo[1,2-e]indolinyl, and 5,11-dihydroindeno[1,2-b]]carbazolyl.

[0039] As used herein, the amine group is —NR 107 R 108 and R 107 and R 108are the same or different and may each 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. The amine group can be selected from the group consisting of -NH2, a monoalkylamine group, a monoarylamine group, a monoheteroarylamine group, 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, but are not limited to, 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.

[0040] In this specification, an arylene group refers to an aryl group having two bonding positions, i.e., a divalent group. The above description of the aryl group may be applied, except that these are both divalent groups. Furthermore, a heteroarylene group refers to a heteroaryl group having two bonding positions, i.e., a divalent group. The above description of the heteroaryl group may be applied, except that these are both divalent groups.

[0041] As used herein, the term "adjacent" refers to a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent sterically closest to the substituent, or another substituent substituted on the atom on which the substituent is substituted. For example, two substituents substituted at ortho positions on a benzene ring and two substituents substituted on the same carbon in an aliphatic ring can be interpreted as being "adjacent" to each other.

[0042] In one embodiment of the present application, a heterocyclic chemical formula compound represented by Chemical Formula 1 is provided.

[0043] In the above Chemical Formula 1, when Z1 is a substituted or unsubstituted, bicyclic or tetracyclic C15 to C60 aryl group having 9 or less protons, L1 may be a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group.

[0044] That is, in the above Chemical Formula 1, when Z1 is a substituted or unsubstituted, bicyclic or tetracyclic C15 to C60 aryl group having 9 or less protons, it is characterized in that it is connected via a linker (L1), and the substituted or unsubstituted, bicyclic or tetracyclic C15 to C60 aryl group having 9 or less protons may be a biphenyl group or a pyrenyl group.

[0045] In this application, when a pyrenyl group belonging to a substituted or unsubstituted bicyclic or tetracyclic C15-C60 aryl group having nine or fewer protons is directly bonded to a triazine group, it may reabsorb the light energy (approximately 2.4 eV) emitted from the green dopant due to its low T1 level (triplet state energy level), thereby reducing the efficiency and lifetime of the device. Therefore, in this case, by linking it to the triazine group via a linker (L1), the efficiency and lifetime of the device can be increased.

[0046] That is, in the above Chemical Formula 1, when Z1 is a biphenyl group or a pyrenyl group, L1 may be a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group.

[0047] In one embodiment of the present application, the chemical formula 1 may be represented by any one of the following chemical formulas 3 to 8. [ka] TIFF0007718715000007.tif187165 TIFF0007718715000008.tif146165 In the above chemical formulas 3 to 8, The definitions of Ar1 to Ar4, L1, and a are the same as those in Chemical Formula 1. X is O; S; or C(R21)(R22); R1 to R5 are the same or different and each independently represent a hydrogen atom; 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; R6 to R9 are the same or different and each independently represent hydrogen; deuterium; a halogen group; —CN; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group containing O or S as a heteroatom; Z11 is -P(=O)RR'; -SiRR'R''; or a substituted or unsubstituted amine group; Z12 and Z13 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 containing O or S as a heteroatom; R, R', and R'' are the same as defined in Chemical Formula 1 above; R21 and R22 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, 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; a1 to d1 are each an integer from 1 to 4, e1 is an integer from 1 to 5, When each of a1 to e1 is 2 or more, the substituents in each parentheses are the same or different, r1 and r2 are each an integer of 0 or 1, The above r1+r2<2.

[0048] In particular, the heterocyclic compounds according to the present application have a sufficiently long substituent or a substituent with a large molecular weight, as represented by the above chemical formulas 3 to 8, and thus the LUMO is not localized from the triazine core to the substituent, thereby effectively stabilizing electrons. As a result, organic light-emitting devices including the heterocyclic compounds have excellent life characteristics.

[0049] In addition, the dipole moment varies depending on the type of terminal substituent of the triazine core structure, allowing for adjustment of molecular mobility. This allows for the selection of an appropriate triazine terminal substituent depending on the charge balance of the device, and the terminal substituent can affect the molecular rigidity and adjust the sublimation temperature, resulting in organic light-emitting devices containing this compound having excellent life characteristics. In other words, an excessively high sublimation temperature can cause the molecules to deteriorate before they sublimate, hindering the efficiency and life of the device.

[0050] In one embodiment of the present application, the chemical formula 1 may be represented by any one of the following chemical formulas 9 to 14. [ka] TIFF0007718715000010.tif200165 In the above chemical formulas 9 to 14, The definitions of L1, Z1, a, and b are the same as those in Chemical Formula 1. Ar11 to Ar14 are the same or different and each independently represent deuterium; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0051] In one embodiment of the present application, Ar1 to Ar4 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.

[0052] In yet another embodiment, Ar1 to Ar4 are the same or different and may each independently represent hydrogen; deuterium; a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0053] In yet another embodiment, Ar1 to Ar4 may be the same or different and may each independently be hydrogen; deuterium; or a substituted or unsubstituted C6 to C40 aryl group.

[0054] In yet another embodiment, Ar1 to Ar4 may be the same or different and may each independently represent hydrogen; deuterium; or a substituted or unsubstituted C6 to C20 aryl group.

[0055] In yet another embodiment, Ar1 to Ar4 may be the same or different and may each independently represent hydrogen; deuterium; or a substituted or unsubstituted C6 to C20 monocyclic or polycyclic aryl group.

[0056] In yet another embodiment, Ar1 to Ar4 may be the same or different and may each independently represent hydrogen; deuterium; or a substituted or unsubstituted C6 to C20 monocyclic aryl group.

[0057] In another embodiment, Ar1 to Ar4 may be the same or different and may each independently be hydrogen; deuterium; or a phenyl group.

[0058] In one embodiment of the present application, Ar11 to Ar14 are the same or different and may each independently represent deuterium; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0059] In yet another embodiment, Ar11 to Ar14 may be the same or different and each independently represent deuterium; or a substituted or unsubstituted C6 to C60 aryl group.

[0060] In yet another embodiment, Ar11 to Ar14 may be the same or different and each independently represent deuterium; or a substituted or unsubstituted C6 to C20 monocyclic aryl group.

[0061] In another embodiment, Ar11 to Ar14 may be deuterium or a phenyl group.

[0062] In one embodiment of the present application, L1 may be a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group.

[0063] In yet another embodiment, L1 may be a direct bond; a substituted or unsubstituted C6 to C40 arylene group; or a substituted or unsubstituted C2 to C40 heteroarylene group.

[0064] In yet another embodiment, L1 may be a direct bond; a C6 to C40 arylene group; or a C2 to C40 heteroarylene group.

[0065] In another embodiment, L1 may be a direct bond; or a C6 to C40 arylene group.

[0066] In yet another embodiment, L1 may be a direct bond; or a C6 to C40 monocyclic or polycyclic arylene group.

[0067] In another embodiment, L1 may be a direct bond; a phenylene group; or a biphenylene group.

[0068] In one embodiment of the present application, Z1 may be selected from the group consisting of halogen; -CN; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C10 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group containing O or S as a heteroatom; -P(=O)RR'; -SiRR'R''; and a substituted or unsubstituted amine group.

[0069] In yet another embodiment, Z1 may be selected from the group consisting of a substituted or unsubstituted C10 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group containing O or S as a heteroatom; and -SiRR'R''.

[0070] In yet another embodiment, Z1 may be selected from the group consisting of a substituted or unsubstituted C10 to C40 aryl group; a substituted or unsubstituted C2 to C40 heteroaryl group containing O or S as a heteroatom; and -SiRR'R''.

[0071] In yet another embodiment, Z1 may be selected from the group consisting of a C10-C40 aryl group unsubstituted or substituted with a C1-C20 alkyl group or a C6-C20 aryl group; a C2-C40 heteroaryl group containing O or S as a heteroatom; and -SiRR'R''.

[0072] In another embodiment, Z1 may be a biphenyl group; a terphenyl group substituted or unsubstituted with a C6-C20 aryl group; a quaterphenyl group substituted or unsubstituted with a C6-C20 aryl group; a quinquephenyl group; a dimethylfluorenyl group; a diphenylfluorenyl group; a spirobifluorenyl group; a triphenylenyl group; a dibenzofuran group; a dibenzothiophene group, or -SiRR'R''.

[0073] In another embodiment, Z1 can be a biphenyl group; a terphenyl group; a dimethylfluorenyl group; a diphenylfluorenyl group; a spirobifluorenyl group; a triphenylenyl group; a dibenzofuran group; a dibenzothiophene group, or -SiRR'R''.

[0074] In one embodiment of the present application, X may be O.

[0075] In one embodiment of the present application, X may be S.

[0076] In one embodiment of the present application, X may be C(R21)(R22).

[0077] In one embodiment of the present application, R1 to R5 are the same or different and may each independently represent hydrogen; 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.

[0078] In yet another embodiment, R1 to R5 may be the same or different and each independently represent hydrogen; or a substituted or unsubstituted C6 to C60 aryl group.

[0079] In yet another embodiment, R1 to R5 may be the same or different and each independently represent hydrogen or a substituted or unsubstituted C6 to C40 aryl group.

[0080] In yet another embodiment, R1 to R5 may be the same or different and may each independently represent hydrogen or a substituted or unsubstituted C6 to C20 aryl group.

[0081] In another embodiment, R1 to R5 may be the same or different and may each independently represent hydrogen or a C6 to C20 aryl group.

[0082] In another embodiment, R1 to R5 may be the same or different and may each independently represent a hydrogen atom, a phenyl group, or a biphenyl group.

[0083] In another embodiment, R3 in Formula 3 may be hydrogen.

[0084] In another embodiment, R4 in Formula 4 may be hydrogen.

[0085] In one embodiment of the present application, R6 to R9 are the same or different and each independently may be hydrogen; deuterium; a halogen group; —CN; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group containing O or S as a heteroatom.

[0086] In another embodiment, R6 to R9 are the same or different and may each independently represent hydrogen; 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 containing O or S as a heteroatom.

[0087] In another embodiment, R6 to R9 may be hydrogen.

[0088] In one embodiment of the present application, Z11 may be -P(=O)RR'; -SiRR'R''; or a substituted or unsubstituted amine group.

[0089] In yet another embodiment, Z11 may be -SiRR'R''.

[0090] In one embodiment of the present application, R, R', and R'' are the same or different and may 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.

[0091] In yet another embodiment, R, R', and R'' may be the same or different and may each independently be a substituted or unsubstituted C1 to C60 alkyl group; or a substituted or unsubstituted C6 to C60 aryl group.

[0092] In another embodiment, R, R', and R'' may be the same or different and may each independently be a C1 to C60 alkyl group; or a C6 to C60 aryl group.

[0093] In yet another embodiment, R, R', and R'' may be the same or different and may each independently be a methyl group or a phenyl group.

[0094] In yet another embodiment, R, R', and R'' may be phenyl groups.

[0095] In one embodiment of the present application, R21 and R22 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, 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.

[0096] In yet another embodiment, R21 and R22 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, or two or more adjacent groups may be bonded to each other to form a substituted or unsubstituted C6 to C40 aromatic hydrocarbon ring.

[0097] In yet another embodiment, R21 and R22 are the same or different and each independently represent a substituted or unsubstituted C1 to C10 alkyl group; or a substituted or unsubstituted C6 to C20 aryl group, or two or more adjacent groups may be bonded to each other to form a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring.

[0098] In yet another embodiment, R21 and R22 are the same or different and each independently represent a C1 to C10 alkyl group; or a C6 to C20 aryl group, or two or more adjacent groups may be bonded to each other to form a C6 to C30 aromatic hydrocarbon ring.

[0099] In another embodiment, R21 and R22 are the same or different and each independently represent a methyl group or a phenyl group, or two or more adjacent groups may be bonded to each other to form a fluorene ring.

[0100] In one embodiment of the present application, R21 and R22 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, or R21 and R22 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.

[0101] In yet another embodiment, R21 and R22 are the same or different and each independently represent a substituted or unsubstituted C1 to C10 alkyl group; or a substituted or unsubstituted C6 to C20 aryl group, or R21 and R22 may be bonded to each other to form a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring.

[0102] In yet another embodiment, R21 and R22 are the same or different and each independently represent a methyl group; or a phenyl group, or R21 and R22 may be bonded to each other to form a fluorene ring.

[0103] In one embodiment of the present application, there is provided a heterocyclic compound represented by any one of the following compounds: [ka] TIFF0007718715000012.tif162165 TIFF0007718715000013.tif170165 TIFF0007718715000014.tif161165 TIFF0007718715000015.tif167165 TIFF0007718715000016.tif159165 TIFF0007718715000017.tif162165 TIFF0007718715000018.tif172165 TIFF0007718715000019.tif175165 TIFF0007718715000020.tif174165 TIFF0007718715000021.tif171165 TIFF0007718715000022.tif187165 TIFF0007718715000023.tif172165 TIFF0007718715000024.tif186165 TIFF0007718715000025.tif172165 TIFF0007718715000026.tif169165 TIFF0007718715000027.tif175165 TIFF0007718715000028.tif167165 TIFF0007718715000029.tif170165 TIFF0007718715000030.tif113165

[0104] In addition, compounds having the inherent properties of the introduced substituents may be synthesized by introducing various substituents into the structure of Chemical Formula 1. For example, by introducing into the core structure substituents that are primarily used in hole injection layer materials, hole transport materials, light emitting layer materials, electron transport layer materials, and charge generation layer materials used in the manufacture of organic light emitting devices, it is possible to synthesize materials that satisfy the requirements of each organic layer. Furthermore, by introducing various substituents into the structure of Chemical Formula 1, it is possible to finely adjust the energy band gap, while improving the properties at the interface between organic materials, thereby diversifying the uses of the material.

[0105] On the other hand, the compound has a high glass transition temperature (Tg) and excellent thermal stability, which is an important factor in providing the device with operational stability.

[0106] Furthermore, in one embodiment of the present application, there is provided an organic light-emitting device comprising: a first electrode; a second electrode provided opposite the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers contains a heterocyclic compound represented by Chemical Formula 1.

[0107] In one embodiment of the present application, the first electrode may be an anode and the second electrode may be a cathode.

[0108] In yet another embodiment, the first electrode may be a cathode and the second electrode may be an anode.

[0109] In one embodiment of the present application, the organic light-emitting device may be a blue organic light-emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material for the blue organic light-emitting device.

[0110] In one embodiment of the present application, the organic light-emitting device is a green organic light-emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material for the green organic light-emitting device.

[0111] In one embodiment of the present application, the organic light-emitting device is a red organic light-emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material for the red organic light-emitting device.

[0112] 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 an emission layer material of the blue organic light-emitting device.

[0113] In one embodiment of the present application, the organic light-emitting device is a green organic light-emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a light-emitting layer material of the green organic light-emitting device.

[0114] 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 an emission layer material of the red organic light-emitting device.

[0115] The specific details regarding the heterocyclic compound represented by Chemical Formula 1 are the same as those described above.

[0116] The organic light-emitting device of the present invention may be manufactured by a conventional method and material for manufacturing an organic light-emitting device, except that one or more organic material layers are formed using the heterocyclic compound described above.

[0117] The heterocyclic compound may be formed in the organic material layer by a solution coating method, such as a vacuum deposition method, during the manufacture of the organic light emitting device, including, but not limited to, spin coating, dip coating, inkjet printing, screen printing, spraying, and roll coating.

[0118] The organic material layer of the organic light-emitting device of the present invention may have a single-layer structure, or may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as organic material layers. However, the structure of the organic light-emitting device is not limited thereto, and the device may include a fewer number of organic material layers.

[0119] In the organic light-emitting device of the present invention, the organic material layer may include a light-emitting layer, and the light-emitting layer may include a heterocyclic compound.

[0120] In an organic light emitting device according to an embodiment of the present application, the organic material layer containing the heterocyclic compound represented by Chemical Formula 1 further contains a heterocyclic compound represented by Chemical Formula 2: [ka] In the above Chemical Formula 2, Rc and Rd are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, a halogen group, -CN, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C60 cycloalkyl group, a substituted or unsubstituted C2-C60 heterocycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C2-C60 heteroaryl group, -Si(R10)(R11)(R12); -P(=O)(R10)(R11); 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-C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2-C60 heterocycle; R10, R11, and R12 are the same or different and each independently represent hydrogen; deuterium; -CN; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group; Ra and Rb are the same or different and each independently represent a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; r and s are each an integer of 0 to 7, When r and s are each 2 or greater, the substituents in each bracket are the same or different.

[0121] When the heterocyclic compound of Formula 1 and the heterocyclic compound of Formula 2 are contained in the organic material layer of an organic light emitting device, better efficiency and lifespan effects are exhibited. This result suggests that an exciplex phenomenon occurs when both compounds are contained simultaneously.

[0122] The exciplex phenomenon is a phenomenon in which electron exchange between two molecules releases energy at the HOMO level of the donor (p-host) and the LUMO level of the acceptor (n-host). When the exciplex phenomenon between two molecules occurs, reverse intersystem crossing (RISC) occurs, which can increase the internal quantum efficiency of fluorescence to 100%. When a donor (p-host) with good hole transporting ability and an acceptor (n-host) with good electron transporting ability are used as the host in the emitting layer, holes are injected into the p-host and electrons are injected into the n-host, which reduces the driving voltage and helps improve lifetime.

[0123] In one embodiment of the present application, the chemical formula 2 may be represented by the following chemical formula 2-1 or 2-2. [ka] In the above chemical formulas 2-1 and 2-2, The definitions of Rc, Rd, r, and s are the same as those in Chemical Formula 2. Ra1, Rb1, and Rc1 are the same or different and each independently represent a substituted or unsubstituted C6 to C60 aryl group; R1' and R2' are the same or different and are each independently selected from the group consisting of hydrogen; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C6-C60 aryl group; and a substituted or unsubstituted C2-C60 heteroaryl group; L1' is a direct bond; or a substituted or unsubstituted C6-C60 arylene group; Ar1' is a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group containing at least one of S and O; m' is an integer from 0 to 4, n' is an integer from 0 to 2, When m' is 2 or greater or n' is 2, the substituents within each bracket are the same or different.

[0124] In one embodiment of the present application, Rc and Rd in the above formula 2 may be hydrogen.

[0125] In one embodiment of the present application, Ra1 and Rb1 in the above Chemical Formula 2-1 may be the same or different, and may each independently be a substituted or unsubstituted C6 to C60 aryl group.

[0126] In another embodiment, Ra1 and Rb1 in the above Chemical Formula 2-1 may be the same or different and may each independently be a substituted or unsubstituted C6 to C40 aryl group.

[0127] In another embodiment, Ra1 and Rb1 in Chemical Formula 2-1 may be the same or different and each independently represent a C6 to C40 aryl group substituted or unsubstituted with at least one substituent selected from the group consisting of a C1 to C40 alkyl group, a C6 to C40 aryl group, -CN, and -Si(R104)(R105)(R106).

[0128] In another embodiment, Ra1 and Rb1 in Chemical Formula 2-1 may be the same or different and each independently represent a phenyl group, a phenyl group substituted or unsubstituted with -CN or -Si(R104)(R105)(R106); a biphenyl group substituted or unsubstituted with a phenyl group; a naphthyl group; a fluorenyl group substituted or unsubstituted with a methyl group or a phenyl group; a spirobifluorenyl group; or a triphenylenyl group.

[0129] In one embodiment of the present application, R104, R105, and R106 in the above formula 2-1 may be a phenyl group.

[0130] In one embodiment of the present application, Rc1 in the above Chemical Formula 2-2 may be a substituted or unsubstituted C6 to C60 aryl group.

[0131] In another embodiment, Rc1 in Chemical Formula 2-2 may be a substituted or unsubstituted C6 to C40 aryl group.

[0132] In another embodiment, Rc1 in Chemical Formula 2-2 may be a C6 to C40 aryl group.

[0133] In another embodiment, Rc1 in Chemical Formula 2-2 may be a phenyl group.

[0134] In one embodiment of the present application, R1' and R2' in Chemical Formula 2-2 may be the same or different and may each independently be selected from the group consisting of hydrogen; 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.

[0135] In yet another embodiment, R1' and R2' in Chemical Formula 2-2 may be the same or different and may each independently be selected from the group consisting of hydrogen; a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C6 to C40 aryl group; and a substituted or unsubstituted C2 to C40 heteroaryl group.

[0136] In another embodiment, R1' and R2' in Chemical Formula 2-2 may be the same or different and may each be independently selected from the group consisting of hydrogen; a C1 to C40 alkyl group; a C6 to C40 aryl group; and a C2 to C40 heteroaryl group.

[0137] In another embodiment, R1' and R2' in Formula 2-2 may be hydrogen.

[0138] In one embodiment of the present application, L1' in Chemical Formula 2-2 may be a direct bond; or a substituted or unsubstituted C6 to C60 arylene group.

[0139] In yet another embodiment, L1' in Chemical Formula 2-2 may be a direct bond; or a substituted or unsubstituted C6 to C40 arylene group.

[0140] In yet another embodiment, L1' in Chemical Formula 2-2 may be a direct bond; or a substituted or unsubstituted C6 to C20 arylene group.

[0141] In another embodiment, L1' in the above Chemical Formula 2-2 may be a direct bond; or a C6 to C20 arylene group.

[0142] In yet another embodiment, L1' in Chemical Formula 2-2 may be a direct bond; or a phenylene group.

[0143] In one embodiment of the present application, Ar1' in Chemical Formula 2-2 may be a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group containing at least one of S and O.

[0144] In another embodiment, Ar1' in Chemical Formula 2-2 may be a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group containing at least one of S and O.

[0145] In yet another embodiment, Ar1' in Chemical Formula 2-2 may be a C6 to C40 aryl group substituted or unsubstituted with a C1 to C10 alkyl group; or a C2 to C40 heteroaryl group substituted or unsubstituted and containing at least one of S and O.

[0146] In another embodiment, Ar1' in Chemical Formula 2-2 may be a phenyl group, a biphenyl group, a naphthyl group, a dimethylfluorenyl group, a dibenzothiophene group, or a dibenzofuran group.

[0147] In one embodiment of the present application, the Chemical Formula 2 may be represented by any of the following compounds: [ka] TIFF0007718715000034.tif161165 TIFF0007718715000035.tif163165 TIFF0007718715000036.tif169165 TIFF0007718715000037.tif245165 TIFF0007718715000038.tif170165 TIFF0007718715000039.tif162165 TIFF0007718715000040.tif170165 TIFF0007718715000041.tif188165 TIFF0007718715000042.tif160165

[0148] Another embodiment of the present application provides a composition for an organic material layer of an organic light-emitting device, comprising the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2.

[0149] The specific details of the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2 are the same as those described above.

[0150] 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.

[0151] The composition can be used when forming an organic material of an organic light-emitting device, and is particularly preferably used when forming a host for the light-emitting layer.

[0152] In one embodiment of the present application, the organic layer includes the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2, and may be used together with a phosphorescent dopant.

[0153] In one embodiment of the present application, the organic layer includes the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2, and may be used together with an iridium-based dopant.

[0154] The phosphorescent dopant material may be any material known in the art.

[0155] For example, phosphorescent dopant materials represented by LL'MX', LL'L''M, LMX'X'', L2MX' and L3M can be used, but these examples do not limit the scope of the present invention. Here, L, L', L'', X' and X'' are different bidentate ligands, and M is a metal that forms an octahedral complex.

[0156] M may be iridium, platinum, osmium, or the like.

[0157] L is an anionic bidentate ligand coordinated to M in the iridium-based dopant through sp2 carbon and heteroatoms, and X may function as an electron or hole trap. Non-limiting examples of L include 2-(1-naphthyl)benzoxazole, (2-phenylbenzoxazole), (2-phenylbenzothiazole), (2-phenylbenzothiazole), (7,8-benzoquinoline), (thiophene-based pyridine), phenylpyridine, benzothiophene-based pyridine, 3-methoxy-2-phenylpyridine, thiophene-based pyridine, and tolylpyridine. Non-limiting examples of X' and X" include acetylacetonate (acac), hexafluoroacetylacetonate, salicylidene, picolinate, and 8-hydroxyquinolinate.

[0158] More specific examples are shown below, but the present invention is not limited to these examples. [ka]

[0159] In one embodiment of the present application, the iridium-based dopant may be Ir(ppy)3 as a green phosphorescent dopant.

[0160] In one embodiment of the present application, the content of the dopant may be 1% to 15%, preferably 3% to 10%, and more preferably 5% to 10%, based on the entire light-emitting layer.

[0161] 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 injection layer or the electron transport layer may include the heterocyclic compound.

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

[0163] In another organic light-emitting device, the organic layer may include an electron transport layer, a light-emitting layer, or a hole-blocking layer, and the electron transport layer, the light-emitting layer, or the hole-blocking layer may include the heterocyclic compound.

[0164] 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.

[0165] 1 to 3 illustrate examples of the stacking order of electrodes and organic layers of an organic light-emitting device according to an 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 may also be applied to the present application.

[0166] 1 shows an organic light emitting device in which an anode 200, an organic material layer 300, and a cathode 400 are sequentially stacked on a substrate 100. However, the present invention is not limited to this structure, and an organic light emitting device in which a cathode, an organic material layer, and an anode are sequentially stacked on a substrate, as shown in FIG.

[0167] Fig. 3 illustrates an example in which the organic material layer is multilayered. The organic light-emitting device in Fig. 3 includes a hole injection layer 301, a hole transport layer 302, an emitting layer 303, a hole blocking layer 304, an electron transport layer 305, and an electron injection layer 306. However, the scope of the present application is not limited to such a stacked structure. Layers other than the emitting layer may be omitted as needed, and other necessary functional layers may be further added.

[0168] In one embodiment of the present application, there is provided a method for manufacturing an organic light-emitting device, the method including the steps of: preparing a substrate; forming a first electrode on the substrate; forming one or more organic material layers on the first electrode; and forming a second electrode on the organic material layers, wherein the step of forming the organic material layers includes forming one or more organic material layers using a composition for an organic material layer according to one embodiment of the present application.

[0169] In one embodiment of the present application, there is provided a method for manufacturing an organic light-emitting device, wherein the step of forming the organic material layer comprises pre-mixing the heterocyclic compound of Chemical Formula 1 and the heterocyclic compound of Chemical Formula 2 and forming the organic material layer using a thermal vacuum deposition method.

[0170] The term "pre-mixed" means that the heterocyclic compound of Formula 1 and the heterocyclic compound of Formula 2 are mixed and placed in a single source before being deposited on an organic layer.

[0171] The premixed materials may be referred to as an organic layer composition according to one embodiment of the present application.

[0172] The organic layer containing the compound represented by Chemical Formula 1 may further contain other materials as needed.

[0173] The organic layer containing both Chemical Formula 1 and Chemical Formula 2 may further contain other materials as needed.

[0174] In an organic light-emitting device according to an embodiment of the present application, materials other than the compound of Chemical Formula 1 or Chemical Formula 2 are exemplified below, but these are for illustrative purposes only and are not intended to limit the scope of the present application, and may be replaced with materials known in the art.

[0175] The anode material may be a material with a relatively large work function, such as a transparent conductive oxide, a metal, or a conductive polymer. Specific examples of the anode material include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

[0176] The cathode material may be a material with a relatively low work function, such as a metal, metal oxide, conductive polymer, etc. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; and multilayer structures such as LiF / Al or LiO2 / Al.

[0177] As the hole injection material, known hole injection materials can be used, for example, phthalocyanine compounds such as copper phthalocyanine disclosed in U.S. Pat. No. 4,356,429, or starburst-type amine derivatives described in the literature [Advanced Material, 6, p. 677 (1994)], such as tris(4-carbazoyl-9-ylphenyl)amine (TCTA), 4,4′,4″-tri[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB), and soluble conductive polymers such as polyaniline / dodecylbenzenesulfonic acid (Polyaniline / Dodecylbenzenesulfonic acid). Alternatively, poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate), polyaniline / camphorsulfonic acid, or polyaniline / poly(4-styrenesulfonate) may be used.

[0178] As the hole transport material, pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, etc. can be used, and low-molecular or high-molecular materials may also be used.

[0179] Examples of electron transport materials that can be used include oxadiazole derivatives, anthraquinodimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinodimethane and its derivatives, fluorenone derivatives, diphenyldicyanoethylene and its derivatives, diphenoquinone derivatives, and metal complexes of 8-hydroxyquinoline and its derivatives. Not only low molecular weight substances but also high molecular weight substances may be used.

[0180] As the electron injection material, for example, LiF is typically used in the industry, but the present application is not limited to this.

[0181] 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, the two or more light-emitting materials may be vapor-deposited from separate supply sources, or may be premixed and vapor-deposited from a single 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 contribute to light emission.

[0182] When a mixture of hosts of light-emitting materials is used, hosts of the same series may be mixed and used, or hosts of different series may be mixed and used. For example, two or more materials selected from either n-type host materials or p-type host materials may be used as the host material of the light-emitting layer.

[0183] The organic light emitting device according to an embodiment of the present application can be top-emitting, back-emitting, or dual-emitting, depending on the materials used.

[0184] The heterocyclic compound according to an embodiment of the present application can function in organic electronic devices including organic solar cells, organic photoreceptors, organic transistors, etc., based on the same principles as those applied to organic light-emitting devices. [Example]

[0185] The present invention will be described in more detail below through examples, which are intended to illustrate the present application and are not intended to limit the scope of the present application.

[0186] <Production example> <Production Example 1> Production of Compound 1-1 [ka] 1) Preparation of Intermediate 1-1-1 10.0 g (59.8 mM) of 9H-carbazole was dissolved in THF and the mixture was purged with nitrogen at -78 °C. 28.7 mL (71.8 mM) of 2.5 M n-BuLi was slowly added at -78 °C and stirred for 30 minutes. 5.5 g (29.9 mM) of 2,4,6-trichloro-1,3,5-triazine was added and stirred at room temperature for 2 hours. After the reaction was complete, the mixture was extracted with distilled water and DCM at room temperature. The organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reaction product was recrystallized from methanol to yield 10.9 g (82%) of intermediate 1-1-1.

[0187] 2) Preparation of Compound 1-1 Intermediate 1-1-1 (10 g, 22.42 mM), [1,1':2',1''-terphenyl]-2-ylboronic acid (6.8 g, 24.67 mM), Pd(PPh3) (41.3 g, 1.1 mM), and K2CO3 (6.2 g, 44.84 mM) were dissolved in 250 mL / 50 mL of 1,4-dioxane / HO and refluxed for 24 hours. After completion of the reaction, the mixture was extracted with distilled water and DCM at room temperature. The organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex = 1:3) and recrystallized from methanol to yield 12.3 g (86%) of the target compound 1-1. The target compound was synthesized in the same manner as in Production Example 1, except that Compound A in Table 1 below was used instead of [1,1':2',1''-terphenyl]-2-ylboronic acid.

[0188] [Table 1] JPEG0007718715000046.jpg191169 JPEG0007718715000047.jpg82169

[0189] <Production Example 2> Production of Compound 1-177 [ka] 1) Preparation of Intermediate 1-177-2 10.0 g (59.8 mM) of 9H-carbazole was dissolved in THF and the mixture was purged with nitrogen at -78 °C. 28.7 mL (71.8 mM) of 2.5 M n-BuLi was slowly added at -78 °C and stirred for 30 minutes. 10.9 g (59.8 mM) of 2,4,6-trichloro-1,3,5-triazine was added and stirred at room temperature for 2 hours. After the reaction was complete, the mixture was extracted with distilled water and DCM at room temperature. The organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reaction mixture was recrystallized from methanol to yield 15.6 g (83%) of intermediate 1-177-2.

[0190] 2) Preparation of Intermediate 1-177-1 14.5 g (59.8 mM) of 2-phenyl-9H-carbazole was dissolved in THF and the mixture was purged with nitrogen at -78 °C. 28.7 mL (71.8 mM) of 2.5 M n-BuLi was slowly added at -78 °C and stirred for 30 minutes. 18.8 g (59.8 mM) of intermediate 1-177-2 was added and stirred at room temperature for 2 hours. After the reaction was complete, the mixture was extracted with distilled water and DCM at room temperature. The organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reaction mixture was recrystallized from methanol to yield 25.6 g (82%) of intermediate 1-177-1.

[0191] 2) Preparation of Compound 1-177 Intermediate 1-177-1 (11.7 g, 22.42 mM), [1,1':2',1''-terphenyl]-4-ylboronic acid (6.8 g, 24.67 mM), Pd(PPh3) (41.3 g, 1.1 mM), and K2CO3 (6.2 g, 44.84 mM) were dissolved in 250 mL / 50 mL of 1,4-dioxane / HO and refluxed for 24 hours. After completion of the reaction, the mixture was extracted with distilled water and DCM at room temperature. The organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reaction mixture was purified by column chromatography (DCM:Hex = 1:3) and recrystallized from methanol to yield 13.6 g (85%) of the target compound 1-177. The target compound was synthesized in the same manner as in Production Example 2, except that compound B in Table 2 below was used instead of [1,1':2',1''-terphenyl]-4-ylboronic acid.

[0192] [Table 2]

[0193] The target compound was synthesized in the same manner as in Preparation Example 1, except that in Preparation Example 1, compound C in Table 3 below was used instead of 9H-carbazole and compound D in Table 3 below was used instead of [1,1':2',1''-terphenyl]-2-ylboronic acid.

[0194] [Table 3]

[0195] <Production Example 3> Production of Compound 2-2 [ka] 1) Preparation of Intermediate 2-2-2 4.2 g (15.8 mM) of 2-bromodibenzo[b,d]thiophene, 6.5 g (15.8 mM) of 9-phenyl-9H,9'H-3,3'-bicarbazole, 3.0 g (15.8 mM) of CuI, 1.9 mL (15.8 mM) of trans-1,2-diaminocyclohexane, and 3.3 g (31.6 mM) of KPO were dissolved in 100 mL of 1,4-oxane and refluxed for 24 hours. After completion of the reaction, the mixture was extracted with distilled water and DCM at room temperature. The organic layer was dried over MgSO and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex = 1:3) and recrystallized from methanol to yield 7.9 g (85%) of intermediate 2-2-2.

[0196] 2) Preparation of Intermediate 2-2-1 A mixture of 8.4 g (14.3 mmol) of intermediate 2-2-2 and 100 mL of THF was added dropwise to 7.4 mL (18.6 mmol) of 2.5 M n-BuLi at -78 °C and stirred at room temperature for 1 hour. 4.8 mL (42.9 mmol) of trimethylborate was added dropwise to the reaction mixture and stirred at room temperature for 2 hours. After the reaction was complete, the mixture was extracted with distilled water and DCM at room temperature. The organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:MeOH = 100:3) and recrystallized from DCM to yield 3.9 g (70%) of intermediate 2-2-1.

[0197] 3) Preparation of Compound 2-2 Intermediate 2-2-1 (6.7 g, 10.5 mM), iodobenzene (2.1 g, 10.5 mM), Pd(PPh)4 (606 mg, 0.52 mM), and KCO3 (2.9 g, 21.0 mM) were dissolved in toluene / EtOH / HO (100 / 20 / 20 mL) and refluxed for 12 hours. After completion of the reaction, the mixture was extracted with distilled water and DCM at room temperature. The organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex = 1:3) and recrystallized from methanol to yield 4.9 g (70%) of the target compound 2-2.

[0198] <Production Example 4> Synthesis of Compound 2-3 Target compound 2-3 (83%) was obtained in the same manner as in Preparation Example 3, except that 4-iodo-1,1'-biphenyl was used instead of iodobenzene.

[0199] <Production Example 5> Synthesis of Compound 2-12 The target compound 2-12 (80%) was obtained in the same manner as in the preparation of compound 2-2, except that 4-iododibenzo[b,d]furan was used instead of iodobenzene in Preparation Example 3.

[0200] <Production Example 6> Synthesis of Compound 3-3 [ka] 3.7 g (15.8 mM) of 3-bromo-1,1'-biphenyl, 6.5 g (15.8 mM) of 9-phenyl-9H,9'H-3,3'-bicarbazole, 3.0 g (15.8 mM) of CuI, 1.9 mL (15.8 mM) of trans-1,2-diaminocyclohexane, and 3.3 g (31.6 mM) of KPO were dissolved in 100 mL of 1,4-dioxane and refluxed for 24 hours. After completion of the reaction, the mixture was extracted with distilled water and DCM at room temperature. The organic layer was dried over MgSO and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex = 1:3) and recrystallized from methanol to yield 7.5 g (85%) of the target compound 3-3. The target compound was synthesized in the same manner as in Production Example 6, except that in Production Example 6, compound E in Table 4 below was used instead of 3-bromo-1,1'-biphenyl and compound F in Table 4 below was used instead of 9-phenyl-9H,9'H-3,3'-bicarbazole.

[0201] [Table 4]

[0202] The remaining compounds other than those listed in Tables 1 to 4 were also produced in the same manner as in the above Production Examples. Tables 5 and 6 below show the synthesized compounds. 1 The H NMR data and FD-MS data can be used to confirm that the target compound has been synthesized.

[0203] [Table 5] TIFF0007718715000055.tif242169 TIFF0007718715000056.tif250169 TIFF0007718715000057.tif39169

[0204] [Table 6] TIFF0007718715000059.tif22169

[0205] <Experimental Example 1> -Fabrication of organic light-emitting devices A glass substrate coated with a 1,500Å thick ITO (indium tin oxide) thin film was ultrasonically cleaned in distilled water. After the distilled water cleaning, it was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UVO (ultraviolet ozone) for 5 minutes using UV in a UV (ultraviolet) cleaner. The substrate was then transferred to a plasma cleaner (PT) and plasma treated in a vacuum to remove the ITO work function and residual film, before being transferred to a thermal evaporation system for organic deposition. 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'-Di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine), were formed on the ITO transparent electrode (anode). An emitting layer was then formed thereon by thermal vacuum deposition as follows: The emitting layer was formed by depositing a compound of Formula 1 (see Table 6 below) as a host to a thickness of 400 Å, and doping a green phosphorescent dopant [Ir(ppy)3] to a thickness of 7% of the emitting layer deposition thickness. Then, BCP (bathocuproine) was deposited to a thickness of 60 Å as a hole-blocking layer, and Alq3 was deposited to a thickness of 200 Å as an electron-transporting layer on top of that. Finally, lithium fluoride (LiF) was deposited to a thickness of 10 Å on the electron-transporting layer to form an electron-injecting layer, and then an aluminum (Al) cathode was deposited to a thickness of 1,200 Å on the electron-injecting layer to form a cathode, completing the fabrication of an organic electroluminescent device. On the other hand, all the organic compounds required for manufacturing OLED elements are 10- 6 ~10- 8 It was purified by vacuum sublimation under torr and used for OLED fabrication. The electroluminescence (EL) characteristics of the organic electroluminescent 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 measured using a lifespan measurement device (M6000) manufactured by Mac Science. 2 When T 90 was measured. The driving voltage, luminous efficiency, color (EL color), and lifespan of the organic light emitting device manufactured according to the present invention were measured, and the results are shown in Table 7 below.

[0206] [Table 7] JPEG0007718715000061.jpg63169

[0207] [ka]

[0208] As can be seen from the results in Table 7 above, the organic electroluminescent elements using the light-emitting layer materials of the organic electroluminescent elements of the present invention not only had lower driving voltages and improved luminous efficiency but also significantly improved lifetimes compared to Comparative Examples 1 to 18.

[0209] Specifically, in Table 8 below, the LUMO orbital of compound 1-298 (Example 17) is decentralized to the triazine and terphenyl group substituents. However, when the triazine group does not have a sufficiently long aryl substituent, as in compounds Ref. 4, 7, 8, 11, 14, 16, and 19, the LUMO orbital of the triazine is decentralized to the short aryl substituent, preventing effective electron stabilization, resulting in a shortened lifetime.

[0210] [Table 8] JPEG0007718715000064.jpg118169

[0211] In Table 9 below, when all carbazole groups are substituted on the triazine group, as in compounds Ref. 1, 9, and 10, the LUMO orbital of the triazine is decentralized to the carbazole. Triazine, which has electron-attracting properties, effectively stabilizes electrons, while carbazole, which has electron-pushing properties, cannot effectively stabilize electrons, resulting in a shortened lifetime.

[0212] [Table 9]

[0213] When the triazine group is substituted with a pyrimidine, cyano, or pyridine group, as in the compounds of Ref. 2, 3, 6, 17, and 18, it was confirmed that the electron mobility increases excessively, the balance between holes and electrons in the light-emitting layer is disrupted, and the lifetime is reduced.

[0214] When phenyl groups are substituted at the 3rd and 4th positions of carbazole, as in compounds Ref. 11, 12, 13, 15, and 16, the molecular weight is higher than that of unsubstituted carbazole, resulting in a higher sublimation temperature. Furthermore, the structural twist is smaller than that of carbazole substituted with a phenyl group at the 2nd position, resulting in a relatively planar structure and a higher sublimation temperature. It was confirmed that prolonged exposure to high sublimation temperatures causes degradation of organic compounds, resulting in a reduced lifespan.

[0215] It was confirmed that when carbazole is substituted with amine or carbazole, as in the compounds of Ref. 6, 7, and 8, the hole mobility increases excessively, the balance between holes and electrons in the light-emitting layer is disrupted, and the lifetime is reduced.

[0216] The compound in Ref. 10 has pyridine bonded instead of triazine, which reduces the electron mobility and disrupts the balance between holes and electrons in the light-emitting layer, resulting in a shorter lifetime.

[0217] In the compound of Reference 5 in Table 10 below, a pyrene group is directly bonded to triazine. It was confirmed that substituted pyrene reabsorbs the light energy (approximately 2.4 eV) emitted from the green dopant due to its low T1 level, reducing the efficiency and lifetime of the device. Pyrene with a low T1 level is primarily used as a dopant in fluorescent OLED devices, rather than the phosphorescent OLED devices described above, and the principle is to prevent T1 energy transfer and promote S1 energy transfer to drive the device.

[0218] [Table 10]

[0219] <Experimental Example 2> -Fabrication of organic light-emitting devices A glass substrate coated with a 1,500Å thick ITO (indium tin oxide) thin film was ultrasonically cleaned in distilled water. After the distilled water cleaning, it was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UVO (ultraviolet ozone) for 5 minutes using UV in a UV (ultraviolet) cleaner. The substrate was then transferred to a plasma cleaner (PT) and plasma treated in a vacuum to remove the ITO work function and residual film, before being transferred to a thermal evaporation system for organic deposition.

[0220] 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'-Di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine), were formed on the ITO transparent electrode (anode). An emitting layer was then formed thereon by thermal vacuum deposition as follows. The emitting layer was formed by premixing one compound of Chemical Formula 1 and one compound of Chemical Formula 2 as hosts in the weight ratios shown in Table 11 below, and then depositing the premixed mixture to a thickness of 400 Å from a single source. A green phosphorescent dopant, Ir(ppy)3, was doped at 7% of the emitting layer deposition thickness. Next, BCP (bathocuproine) was deposited to a thickness of 60 Å as a hole-blocking layer, and Alq3 was deposited to a thickness of 200 Å as an electron-transporting layer. Finally, lithium fluoride (LiF) was deposited to a thickness of 10 Å on the electron-transporting layer to form an electron-injecting layer. An aluminum (Al) cathode was then deposited to a thickness of 1,200 Å on the electron-injecting layer to form a cathode, completing the fabrication of an organic electroluminescent device. On the other hand, all the organic compounds required for manufacturing OLED elements are 10 -8 ~10 -6 It was purified by vacuum sublimation under torr and used for OLED fabrication. The electroluminescence (EL) characteristics of the organic electroluminescent 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 measured using a lifespan measurement device (M6000) manufactured by Mac Science. 2 When T 90 was measured.

[0221] The driving voltage, luminous efficiency, color coordinate (CIE), and lifespan of the organic light emitting device manufactured according to the present invention were measured, and the results are shown in Table 11 below.

[0222] [Table 11]

[0223] The results in Table 11 show that the compound of Formula 1 (n type) and the compound of Formula 2 are combined to exhibit superior efficiency and lifespan. This result suggests that an exciplex phenomenon occurs when the two compounds are combined.

[0224] The exciplex phenomenon is a phenomenon in which electron exchange between two molecules releases energy equivalent to the HOMO level of the donor (p-host) and the LUMO level of the acceptor (n-host). When the exciplex phenomenon between two molecules occurs, reverse intersystem crossing (RISC) occurs, which can increase the internal quantum efficiency of fluorescence to 100%. When a donor (p-host) with good hole transporting ability and an acceptor (n-host) with good electron transporting ability are used as hosts in the emissive layer, holes are injected into the p-host and electrons are injected into the n-host, which reduces the driving voltage and improves the lifetime. In the present invention, it has been confirmed that excellent device characteristics are exhibited when the compound of Chemical Formula 2 acts as a donor and the compound of Chemical Formula 1 acts as an acceptor and is used together as a host in the emissive layer. [Explanation of symbols]

[0225] 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 any one of the following chemical formulas 3 to 8: 【Chemistry 19】 【change】 【change】 In the above Chemical Formulas 3 to 8, Ar1 to Ar4 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; L1 is a direct bond; or a substituted or unsubstituted C6-C60 arylene group; X is O; S; or C(R21)(R22), R1 to R5 are the same or different and each independently represent a hydrogen atom, a phenyl group, or a biphenyl group; R6 to R9 are the same or different and each independently represent hydrogen or deuterium; Z11 is —SiRR′R″; Z12 and Z13 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 containing O or S as a heteroatom; R21 and R22 are the same or different and each independently represent a methyl or phenyl group, or two or more adjacent groups are bonded to each other to form a fluorene ring; R, R', and R'' are the same or different and each independently represent a substituted or unsubstituted phenyl group; a is an integer from 1 to 4, a1 to d1 are each an integer of 1 to 4, e1 is an integer from 1 to 5, When each of a and a1 to e1 is 2 or more, the substituents in each bracket are the same or different, r1 and r2 are each 0.

2. "Substituted or unsubstituted" means substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium; halogen; cyano group; 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 substituted or unsubstituted with a substituent in which two or more substituents selected from the above-exemplified substituents are linked together, The heterocyclic compound according to claim 1, wherein R, R', and R'' are defined as in the formulae 3 to 8.

3. The heterocyclic compound according to claim 1, wherein any one of the chemical formulas 3 to 8 is represented by any one of the following compounds: 【Chemical 21】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】

4. An organic light-emitting device comprising: a first electrode; a second electrode provided opposite the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers contains the heterocyclic compound according to any one of claims 1 to 3.

5. The organic light emitting device according to claim 4 , wherein the organic material layer containing a heterocyclic compound further contains a heterocyclic compound represented by the following Chemical Formula 2: 【Chemical 22】 In the above Chemical Formula 2, Rc and Rd are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, a halogen group, -CN, a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C2 to C60 alkenyl group, a substituted or unsubstituted C2 to C60 alkynyl group, a substituted or unsubstituted C1 to C60 alkoxy group, a substituted or unsubstituted C3 to C60 cycloalkyl group, a substituted or unsubstituted C2 to C60 heterocycloalkyl group, a substituted or unsubstituted C6 to C60 aryl group, a substituted or unsubstituted C2 to C60 heteroaryl group, -Si(R10)(R11)(R12); -P(=O)(R10)(R11); 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; R10, R11, and R12 are the same or different and each independently represent hydrogen; deuterium; —CN; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group; Ra and Rb are the same or different and each independently represent a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; r and s are each an integer from 0 to 7; When r and s are each 2 or greater, the substituents in each bracket may be the same or different.

6. The organic light-emitting device according to claim 5, wherein the chemical formula 2 is represented by the following chemical formula 2-1 or chemical formula 2-2: 【Chemical 23】 In the chemical formulas 2-1 and 2-2, The definitions of Rc, Rd, r, and s are the same as those in Chemical Formula 2. Ra1, Rb1, and Rc1 are the same or different and each independently represent a substituted or unsubstituted C6 to C60 aryl group; R1' and R2' are the same or different and are each independently selected from the group consisting of hydrogen; 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; L1' is a direct bond; or a substituted or unsubstituted C6-C60 arylene group; Ar1' is a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group containing at least one of S and O; m' is an integer from 0 to 4, n' is an integer from 0 to 2, When m' is 2 or greater or n' is 2, the substituents within each bracket are the same or different.

7. The organic light-emitting device according to claim 5, wherein the heterocyclic compound represented by Chemical Formula 2 is any one selected from the following compounds: 【Chemistry 24】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】

8. The organic light-emitting device according to claim 5 , wherein R c and R d are hydrogen.

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

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

11. The organic light-emitting device according to claim 4 , further comprising one or more layers selected from the group consisting of an emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

12. A composition for an organic layer of an organic light-emitting device, comprising the heterocyclic compound according to any one of claims 1 to 3 and a heterocyclic compound represented by the following chemical formula 2: 【Chemistry 25】 In the above Chemical Formula 2, Rc and Rd are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, a halogen group, -CN, a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C2 to C60 alkenyl group, a substituted or unsubstituted C2 to C60 alkynyl group, a substituted or unsubstituted C1 to C60 alkoxy group, a substituted or unsubstituted C3 to C60 cycloalkyl group, a substituted or unsubstituted C2 to C60 heterocycloalkyl group, a substituted or unsubstituted C6 to C60 aryl group, a substituted or unsubstituted C2 to C60 heteroaryl group, -Si(R10)(R11)(R12); -P(=O)(R10)(R11); 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; R10, R11, and R12 are the same or different and each independently represent hydrogen; deuterium; —CN; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group; Ra and Rb are the same or different and each independently represent a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; r and s are each an integer from 0 to 7; When r and s are each 2 or greater, the substituents in each bracket may be the same or different.

13. The composition for an organic material layer of an organic light-emitting device according to claim 12, wherein the weight ratio of the heterocyclic compound to the heterocyclic compound represented by Chemical Formula 2 in the composition is 1:10 to 10:

1.

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

15. 15. The method of claim 14, wherein the forming of the organic material layer comprises pre-mixing the heterocyclic compound and the heterocyclic compound of Formula 2 and forming the organic material layer using a thermal vacuum deposition method.

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