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

Abstract

The present application provides a heterocyclic compound and an organic light-emitting device in which the heterocyclic compound is contained in an organic material layer.

Description

[Technical field]

[0001] This application claims the benefit of the filing date of Korean Patent Application No. 10-2019-0175166, filed with the Korean Intellectual Property Office on December 26, 2019, the entire contents of which are incorporated herein by reference.

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

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

[0004] An organic light-emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to an organic light-emitting device having such a structure, electrons and holes injected from the two electrodes combine in the organic thin film to form pairs, and then disappear, emitting light. The organic thin film may be composed of a single layer or multiple layers as required.

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

[0006] There is a continuing need to develop materials for organic thin films to improve the performance, lifetime or efficiency of organic light emitting devices. [Prior art documents] [Patent documents]

[0007] [Patent Document 1] U.S. Patent No. 4,356,429 Summary of the Invention [Problem to be solved by the invention]

[0008] The present specification provides a heterocyclic compound, an organic light-emitting device including the same, and a composition for an organic layer of the organic light-emitting device. [Means for solving the problem]

[0009] One embodiment of the present application provides a heterocyclic compound represented by the following formula 1:

[0010] [ka] In the above formula 1, L1 and L2 are the same or different and each independently represents a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms; X is O; S; or NRa; Y1 to Y5 are the same or different from each other and each independently represents N or CRb, and at least one of Y1 to Y5 is N, and when CRb is 2 or more, each Rb is the same or different from each other, R1 is represented by the following formula A, R2 to R9 are each hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms; The Ra is a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, Rb is selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms or a substituted or unsubstituted heterocycle having 2 to 60 carbon atoms; m and n are each independently an integer of 0 to 3, and when m and n are each 2 or more, the substituents in the parentheses are the same or different. p is 0 or 1; [ka] In the formula A, L 11 and L 12 are the same or different and each independently represent a direct bond; a substituted or unsubstituted arylene group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms, Ar 11 and Ar 12 are the same or different and are each independently selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms, or the Ar 11 and Ar 12 are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms or a substituted or unsubstituted heterocycle having 2 to 60 carbon atoms, a and b are each 0 or 1; [ka] means the position at which it bonds to L1 in formula 1.

[0011] Moreover, one embodiment of the present application provides an organic light-emitting device comprising: a first electrode; a second electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein at least one of the organic layers contains a heterocyclic compound represented by Formula 1.

[0012] Finally, one embodiment of the present application provides a composition for an organic layer of an organic light-emitting device, comprising a heterocyclic compound represented by the above formula 1 and any one of the following heterocyclic compounds 1-1 to 1-14.

[0013] [ka] Effect of the Invention

[0014] The heterocyclic compounds described herein may be used as organic layer materials in organic light-emitting devices. The heterocyclic compounds may play the role of hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, etc. in the organic light-emitting devices.

[0015] Specifically, when the heterocyclic compound represented by the formula 1 is used in an organic layer of an organic light-emitting device, the driving voltage of the device can be lowered, the light efficiency can be improved, and the life characteristics of the device can be improved. [Brief description of the drawings]

[0016] [Figure 1] 1 is a diagram illustrating a stacked structure of an organic light-emitting device according to an embodiment of the present application. [Diagram 2] 1 is a diagram illustrating a stacked structure of an organic light-emitting device according to an embodiment of the present application. [Diagram 3] 1 is a diagram illustrating a stacked structure of an organic light-emitting device according to an embodiment of the present application. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0017] The present application will be described in detail below.

[0018] In this specification, when a part is said to "comprise" a certain component, this does not mean that it excludes other components, but that it may further include other components, unless specifically stated to the contrary.

[0019] The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position of the substitution is not limited as long as it is a position at which a hydrogen atom is substituted, i.e., a position at which a substituent can be substituted, and when two or more substituents are substituted, the two or more substituents may be the same or different from each other.

[0020] In this specification, "substituted or unsubstituted" means being substituted or unsubstituted with one or more substituents selected from the group consisting of a linear or branched alkyl group having 1 to 60 carbon atoms; a linear or branched alkenyl group having 2 to 60 carbon atoms; a linear or branched alkynyl group having 2 to 60 carbon atoms; a monocyclic or polycyclic cycloalkyl group having 3 to 60 carbon atoms; a monocyclic or polycyclic heterocycloalkyl group having 2 to 60 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 60 carbon atoms; a monocyclic or polycyclic heteroaryl group having 2 to 60 carbon atoms; a silyl group; a phosphine oxide group; and an amine group, or being substituted or unsubstituted with a substituent to which two or more substituents selected from the above-mentioned exemplary substituents are linked.

[0021] More specifically, in this specification, "substituted or unsubstituted" can mean being substituted or unsubstituted with one or more substituents selected from the group consisting of a monocyclic or polycyclic aryl group having 6 to 60 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 60 carbon atoms.

[0022] In this specification, the halogen may be fluorine, chlorine, bromine or iodine.

[0023] In this specification, the alkyl group includes a straight or branched chain having 1 to 60 carbon atoms, and may be further substituted with other substituents. The number of carbon atoms in the alkyl group may be 1 to 60, specifically 1 to 40, and more specifically 1 to 20. Specific examples include a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a 1-methyl-butyl group, a 1-ethyl-butyl group, a pentyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a hexyl group, an n-hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a 3,3-dimethylbutyl group, a 2-ethylbutyl group, and a heptyl group. , 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, 5-methylhexyl and the like, but are not limited to these.

[0024] In this specification, the alkenyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted with other substituents. The number of carbon atoms in the alkenyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20. Specific examples include vinyl group, 1-propenyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 3-methyl-1-butenyl group, 1,3-butadienyl group, allyl group, 1-phenylvinyl-1-yl group, 2-phenylvinyl-1-yl group, 2,2-diphenylvinyl-1-yl group, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl group, and 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, but are not limited thereto.

[0025] In this specification, the alkynyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted with other substituents. The alkynyl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 2 to 20 carbon atoms.

[0026] In this specification, the alkoxy group may be a straight chain, a branched chain, or a cyclic chain. The number of carbon atoms of the alkoxy group is not particularly limited, but it is preferable that the number of carbon atoms is 1 to 20. Specifically, the alkoxy group may be, but is 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, p-methylbenzyloxy, etc.

[0027] 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, the polycyclic group means a group in which the cycloalkyl group is directly bonded to or condensed with another cyclic group. Here, the other cyclic group may be a cycloalkyl group, but may also be other types of cyclic groups, such as a heterocycloalkyl group, an aryl group, or a heteroaryl group. The number of carbon atoms in the cycloalkyl group may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20. Specific examples of the cycloalkyl group 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.

[0028] In this specification, the heterocycloalkyl group includes O, S, Se, N or Si as a heteroatom, includes a monocyclic or polycyclic group having 2 to 60 carbon atoms, and may be further substituted with other substituents. Here, the polycyclic group means a group in which the heterocycloalkyl group is directly bonded to or condensed with another cyclic group. Here, the other cyclic group may be a heterocycloalkyl group, but may also be other types of cyclic groups, such as a cycloalkyl group, an aryl group, or a heteroaryl group. The number of carbon atoms in the heterocycloalkyl group may be 2 to 60, specifically 2 to 40, more specifically 3 to 20.

[0029] 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 bonded to or condensed with another ring group. Here, the other ring group may be an aryl group, but may also be other types of ring groups, such as a cycloalkyl group, a heterocycloalkyl group, or a heteroaryl group. The aryl group includes a spiro group. The number of carbon atoms of the aryl group may be 6 to 60, specifically 6 to 40, and more specifically 6 to 25. Specific examples of the aryl group include a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a chrysenyl group, a phenanthrenyl group, a perylenyl group, a fluoranthenyl group, a triphenylenyl group, a phenalenyl group, a pyrenyl group, a tetracenyl group, a pentacenyl group, a fluorenyl group, an indenyl group, an acenaphthylenyl group, a benzofluorenyl group, a spirobifluorenyl group, a 2,3-dihydro-1H-indenyl group, and condensed ring groups thereof, but are not limited to these.

[0030] In the present specification, the phosphine oxide group is represented by -P(=O)R101R102, where R101 and R102 may be the same or different and each may independently be a substituent consisting of at least one of hydrogen, deuterium, a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a cycloalkyl group, an aryl group, and a heterocyclic group. Specific examples of the phosphine oxide group include, but are not limited to, a diphenylphosphine oxide group and a dinaphthylphosphine oxide group.

[0031] In this specification, a silyl group is a substituent that contains Si and has the Si atom directly bonded as a radical, and is represented by -SiR104R105R106, where R104 to R106 may be the same or different and each may be independently a substituent consisting of at least one of hydrogen, deuterium, a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a cycloalkyl group, an aryl group, and a heterocyclic group. Specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.

[0032] As used herein, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

[0033] In this specification, the spiro group may be a group containing a spiro structure and may have 15 to 60 carbon atoms. For example, the spiro group may contain a structure in which a 2,3-dihydro-1H-indene group or a cyclohexane group is spiro-bonded to a fluorenyl group. Specifically, the following spiro group may contain any of the groups of the following structural formulas.

[0034] [ka] In this specification, the heteroaryl group includes S, O, Se, N or Si as a heteroatom, includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted with other substituents. Here, the polycyclic ring means a group in which the heteroaryl group is directly bonded to or condensed with another ring group. Here, the other ring group may be a heteroaryl group, but may also be other types of ring groups, such as a cycloalkyl group, a heterocycloalkyl group, an aryl group, etc. The number of carbon atoms of the heteroaryl group may be 2 to 60, specifically 2 to 40, more specifically 3 to 25.Specific examples of the heteroaryl group include a pyridyl group, a pyrrolyl group, a pyrimidyl group, a pyridazinyl group, a furanyl group, a thiophene group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, a furazanyl group, an oxadiazolyl group, a thiadiazolyl group, a dithiazolyl group, a tetrazolyl group, a pyranyl group, a thiopyranyl group, a diazinyl group, an oxazinyl group, a thiazinyl group, a dioxinyl group, a triazinyl group, a tetrazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, an isoquinazolinyl group, a quinozolyl group, a naphthyridyl group, an acridinyl group, a phenanthridinyl group, an imidazopyridinyl group, a diazanaphthalenyl group, a triazaindene group, an indolyl group, an indolizinyl group, a benzothiazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiophene group, a benzofuran group, a dibenzothiophene group, a dibenzofuran group, a carbazolyl group, a benzo Carbazolyl group, dibenzocarbazolyl group, phenazinyl group, dibenzosilole group, spirobi(dibenzosilole), dihydrophenazinyl group, phenoxazinyl group, phenanthridyl group, imidazopyridinyl group, thienyl group, indolo[2,3-a]carbazolyl group, indolo[2,3-b]carbazolyl group, indolinyl group, 10,11-dihydro-dibenzo[b,f]azepine group, 9,10-dihydroacridinyl group, phenanthrazinyl group, phenothiazinyl 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.

[0035] In the present specification, the amine group may be selected from the group consisting of a monoalkylamine group, a monoarylamine group, a monoheteroarylamine group, -NH2, a dialkylamine group, a diarylamine group, a diheteroarylamine group, an alkylarylamine group, an alkylheteroarylamine group, and an arylheteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, a dibiphenylamine group, an anthracenylamine group, a 9-methyl-anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a triphenylamine group, a biphenylnaphthylamine group, a phenylbiphenylamine group, a biphenylfluorenylamine group, a phenyltriphenylenylamine group, and a biphenyltriphenylenylamine group, but are not limited thereto.

[0036] In this specification, the term "arylene group" refers to an aryl group having two bonding positions, i.e., a divalent group. The above description of the aryl group is applicable except that each of these is a divalent group. The term "heteroarylene group" refers to a heteroaryl group having two bonding positions, i.e., a divalent group. The above description of the heteroaryl group is applicable except that each of these is a divalent group.

[0037] In this specification, the term "adjacent" groups may refer to a substituent substituted on an atom directly bonded to the atom on which the substituent is substituted, a substituent sterically closest to the substituent, or another substituent substituted on the atom on which the substituent is substituted. For example, two substituents substituted at the ortho positions on a benzene ring and two substituents substituted on the same carbon on an aliphatic ring may be interpreted as "adjacent" groups to each other.

[0038] In this specification, when "a substituent is not shown in a chemical formula or compound structure," it means that a hydrogen atom is bonded to a carbon atom. However, deuterium ( 2 H, Deuterium) is an isotope of hydrogen, so some hydrogen atoms may be deuterium.

[0039] In one embodiment of the present application, "when no substituent is shown in the chemical formula or the structure of the compound", it can mean that all positions substitutable as a substituent are hydrogen or deuterium. In other words, in the case of deuterium, which is an isotope of hydrogen, some of the hydrogen atoms may be deuterium, which is an isotope of hydrogen, and in this case, the content of deuterium may be 0% to 100%.

[0040] In one embodiment of the present application, in the case where "substituents are not shown in the chemical formula or the structure of the compound", if the deuterium content is 0%, the hydrogen content is 100%, and the substituents do not clearly exclude hydrogen and deuterium, hydrogen and deuterium may be used together in the compound.

[0041] In one embodiment of the present application, deuterium is one of the isotopes of hydrogen and is an element having a deuteron consisting of one proton and one neutron as an atomic nucleus, and can be represented as hydrogen-2, and its atomic symbol can also be written as D or 2H.

[0042] 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.

[0043] In one embodiment of the present application, the content T% of a specific substituent can be defined as T2 / T1×100=T%, where T1 is the total number of substituents that the base compound may have and T2 is the number of specific substituents among the total number of substituents.

[0044] That is, in one example, [ka] In the case of a phenyl group represented by the formula, a deuterium content of 20% can be expressed as 20% when the total number of substituents that the phenyl group can have is 5 (T1 in the formula), of which the number of deuterium is 1 (T2 in the formula). That is, a phenyl group having a deuterium content of 20% can be expressed by the following structural formula.

[0045] [ka] In addition, in one embodiment of the present application, a "phenyl group having a deuterium content of 0%" can mean a phenyl group that does not contain a deuterium atom, that is, a phenyl group that has 5 hydrogen atoms.

[0046] In one embodiment of the present application, there is provided a heterocyclic compound represented by formula 1:

[0047] [ka] In the above formula 1, L1 and L2 are the same or different and each independently represents a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms; X is O; S; or NRa; Y1 to Y5 are the same or different from each other and each independently represents N or CRb, and at least one of Y1 to Y5 is N, and when CRb is 2 or more, each Rb is the same or different from each other, R1 is represented by the following formula A, R2 to R9 are each hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms; The Ra is a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, said Rb is selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms or a substituted or unsubstituted heterocycle having 2 to 60 carbon atoms; m and n are each independently an integer of 0 to 3, and when m and n are each 2 or more, the substituents in the parentheses are the same or different. p is 0 or 1; [ka] In the formula A, L 11 and L 12 are the same or different and each independently represent a direct bond; a substituted or unsubstituted arylene group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms, Ar 11 and Ar 12 are the same or different and are each independently selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms, or the Ar 11 and Ar 12are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms or a substituted or unsubstituted heterocycle having 2 to 60 carbon atoms, a and b are each 0 or 1; [ka] means the position at which it bonds to L1 in formula 1.

[0048] The compound represented by formula 1 has a donor with good hole transport ability and an acceptor with good electron transport ability in one molecule, and has a steric configuration by fixing a substituent at the 11th position of naphthobenzofuran. Since the HOMO (Highest Occupied Molecular Orbital) and LUMO (HOMO (Lowest ighest Unoccupied Molecular Orbital)) are spatially separated, strong charge transfer is possible. Therefore, when used as an organic material in an organic light emitting device, high efficiency is expected.

[0049] In one embodiment of the present application, L1 and L2 in the formula 1 may be the same or different, and each may independently be a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group.

[0050] In still another embodiment, L1 and L2 are the same or different and may each independently be a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.

[0051] In another embodiment, L1 and L2 are the same or different and may each independently be a direct bond; a substituted or unsubstituted arylene group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms.

[0052] In another embodiment, L1 and L2 are the same or different and may each independently be a direct bond; a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms.

[0053] In still another embodiment, L1 and L2 are the same or different and may each independently be a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted biphenylene group.

[0054] In still another embodiment, L1 and L2 are the same or different and may each independently be a direct bond; a phenylene group; or a biphenylene group.

[0055] In one embodiment of the present application, L1 and L2 may be different from each other.

[0056] In one embodiment of the present application, L1 and L2 may be identical to each other.

[0057] In one embodiment of the present application, L1 may be a direct bond, and L2 may be a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.

[0058] In one embodiment of the present application, L1 may be a direct bond, and L2 may be a substituted or unsubstituted arylene group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms.

[0059] In one embodiment of the present application, L1 may be a direct bond, and L2 may be a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms.

[0060] In yet another embodiment, L1 may be a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted biphenylene group.

[0061] In yet another embodiment, L1 may be a direct bond; a phenylene group; or a biphenylene group.

[0062] In yet another embodiment, L1 is a direct bond.

[0063] In yet another embodiment, L1 is a phenylene group.

[0064] In yet another embodiment, L1 is a biphenylene group.

[0065] In one embodiment of the present application, the L2 may be a direct bond, and the L1 may be a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.

[0066] In one embodiment of the present application, the L2 may be a direct bond, and the L1 may be a substituted or unsubstituted arylene group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms.

[0067] In one embodiment of the present application, the L2 may be a direct bond, and the L1 may be a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms.

[0068] In one embodiment of the present application, L2 may be a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.

[0069] In still another embodiment, the L2 may be a direct bond; a substituted or unsubstituted arylene group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms.

[0070] In still another embodiment, the L2 may be a direct bond; a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms.

[0071] In yet another embodiment, L2 may be a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted biphenylene group.

[0072] In yet another embodiment, L2 may be a direct bond; a phenylene group; or a biphenylene group; or a naphthylene group.

[0073] In yet another embodiment, L2 is a direct bond.

[0074] In yet another embodiment, L2 is a phenylene group.

[0075] In yet another embodiment, L2 is a biphenylene group.

[0076] In one embodiment of the present application, m and n in the above formula 1 each independently represent an integer of 0 to 3, and when m and n are 2 or more, the substituents in the parentheses are the same or different from each other.

[0077] In one embodiment of the present application, said m is 3.

[0078] In one embodiment of the present application, said m is 2.

[0079] In one embodiment of the present application, said m is 1.

[0080] In one embodiment of the present application, m is 0.

[0081] In one embodiment of the present application, when m is 2 or more, the substituents in parentheses are the same or different from each other.

[0082] In one embodiment of the present application, n is 3.

[0083] In one embodiment of the present application, n is 2.

[0084] In one embodiment of the present application, n is 1.

[0085] In one embodiment of the present application, n is 0.

[0086] In one embodiment of the present application, when n is 2 or more, the substituents in parentheses are the same or different from each other.

[0087] In one embodiment of the present application, X in formula 1 above may be O; S; or NRa.

[0088] In one embodiment of the present application, X is O; or NRa.

[0089] In one embodiment of the present application, said X is O.

[0090] In one embodiment of the present application, said X may be NRa.

[0091] In one embodiment of the present application, Y1 to Y5 in the formula 1 are the same or different from each other and each independently represents N or CRb, at least one of Y1 to Y5 is N, and when CRb is 2 or more, each Rb may be the same or different from each other.

[0092] In one embodiment of the present application, N among Y1 to Y5 is 1 or more and 3 or less, and the remainder is CRb, and when CRb is 2 or more, each Rb may be the same or different.

[0093] In one embodiment of the present application, the Ra may be a substituted or unsubstituted aryl group having 6 to 40 carbon atoms.

[0094] In one embodiment of the present application, the Ra may be a substituted or unsubstituted aryl group having 6 to 10 carbon atoms.

[0095] In one embodiment of the present application, the Ra may be a substituted or unsubstituted phenyl group.

[0096] In one embodiment of the present application, Ra may be a phenyl group.

[0097] In one embodiment of the present application, Rb is selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, or two or more groups adjacent to each other can be bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms or a substituted or unsubstituted heterocycle having 2 to 60 carbon atoms.

[0098] In one embodiment of the present application, Rb is selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms, or two or more groups adjacent to each other can be bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms or a substituted or unsubstituted heterocycle having 2 to 60 carbon atoms.

[0099] In one embodiment of the present application, Rb can be selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0100] In one embodiment of the present application, Rb can be selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.

[0101] In one embodiment of the present application, Rb can be selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0102] In one embodiment of the present application, Rb may be hydrogen; or deuterium.

[0103] In one embodiment of the present application, Rb is hydrogen.

[0104] In one embodiment of the present application, said Rb is deuterium.

[0105] In one embodiment of the present application, Rb can be selected from the group consisting of substituted or unsubstituted aryl groups having 6 to 60 carbon atoms; and substituted or unsubstituted heteroaryl groups having 2 to 60 carbon atoms.

[0106] In one embodiment of the present application, Rb can be selected from the group consisting of substituted or unsubstituted aryl groups having 6 to 40 carbon atoms; and substituted or unsubstituted heteroaryl groups having 2 to 40 carbon atoms.

[0107] In one embodiment of the present application, Rb can be selected from the group consisting of substituted or unsubstituted aryl groups having 6 to 20 carbon atoms; and substituted or unsubstituted heteroaryl groups having 2 to 20 carbon atoms.

[0108] In one embodiment of the present application, Rb can be selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted dibenzothiophene group; and a substituted or unsubstituted dibenzofuran group.

[0109] In one embodiment of the present application, Rb can be selected from the group consisting of hydrogen; deuterium; a phenyl group, or a phenyl group substituted or unsubstituted with a naphthyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a fluorenyl group substituted or unsubstituted with an alkyl group having 2 to 10 carbon atoms; a substituted or unsubstituted dibenzothiophene group; and a substituted or unsubstituted dibenzofuran group.

[0110] In one embodiment of the present application, Rb can be selected from the group consisting of hydrogen; deuterium; a phenyl group or a phenyl group substituted or unsubstituted with a naphthyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a fluorenyl group substituted or unsubstituted with a methyl group; a substituted or unsubstituted dibenzothiophene group; and a substituted or unsubstituted dibenzofuran group.

[0111] In one embodiment of the present application, the formula 1 can be represented by the following formula 1-1.

[0112] [ka] In the above formula 1-1, the definitions of each substituent are the same as those in formula 1.

[0113] In one embodiment of the present application, the formula 1 can be represented by the following formula 2 or 3.

[0114] [ka] [ka] In the formulae 2 and 3, the definitions of each substituent are the same as those in the formula 1.

[0115] In one embodiment of the present application, the formula 2 can be represented by any of the following formulas 2-1 to 2-6.

[0116] [ka] [ka] [ka] [ka] [ka] [ka] In the formulas 2-1 to 2-6, L 1、 L 2、 X, R 1、 The definitions of m and n are the same as those of Formula 1. Y 11 ~Y 15 is CRb, and the definition of Rb is the same as in formula 1.

[0117] In one embodiment of the present application, the formula 3 can be represented by any of the following formulas 3-1 to 3-6.

[0118] [ka] [ka] [ka] [ka] [ka] [ka] In the formulas 3-1 to 3-6, L 1、 L 2、 X, R 1、 The definitions of m and n are the same as those of Formula 1. Y 11 ~Y 15 is CRb, and the definition of Rb is the same as in formula 1.

[0119] In one embodiment of the present application, R1 can be represented by the following formula A:

[0120] [ka] In the formula A, L 11 and L 12 are the same or different and each independently represent a direct bond; a substituted or unsubstituted arylene group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms, Ar 11 and Ar 12 are the same or different and are each independently selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms, or the Ar 11 and Ar 12are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms or a substituted or unsubstituted heterocycle having 2 to 60 carbon atoms, a and b are 0 or 1; [ka] means the position at which it bonds to L1 in formula 1.

[0121] In one embodiment of the present application, the formula A can be represented by any of the following formulae A-1 to A-5.

[0122] [ka] [ka] [ka] [ka] [ka] In the formulae A-1 to A-5, L 13 and L 14 are the same or different and each independently represent a direct bond; a substituted or unsubstituted arylene group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms, Ar 13 and Ar 14 are the same or different and each independently represent a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms, R 20 ~R 26are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms, X 11 represents O; S; or CRcRd, wherein Rc and Rd may be the same or different and each independently represents a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; c and d are each 0 or 1; [ka] means the position at which it bonds to L1 in formula 1.

[0123] In one embodiment of the present application, L of formula A-1 13 and L 14 may be the same or different and each independently represent a direct bond; a substituted or unsubstituted arylene group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms.

[0124] In one embodiment of the present application, L of formula A-1 13 and L 14 may be the same or different and each independently represent a direct bond; a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms.

[0125] In one embodiment of the present application, the L 13 and L 14 may be the same or different and each independently represent a direct bond; or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

[0126] In one embodiment of the present application, the L 13 and L 14may be the same or different and each independently be a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; or a substituted or unsubstituted naphthylene group.

[0127] In one embodiment of the present application, the L 13 and L 14 may be the same or different and each independently be a direct bond; a phenylene group; a biphenylene group; or a naphthylene group.

[0128] In one embodiment of the present application, the L 13 is a direct bond.

[0129] In one embodiment of the present application, the L 13 is a phenylene group.

[0130] In one embodiment of the present application, the L 13 is a biphenylene group.

[0131] In one embodiment of the present application, the L 13 is a naphthylene group.

[0132] In one embodiment of the present application, the L 14 is a direct bond.

[0133] In one embodiment of the present application, the L 14 is a phenylene group.

[0134] In one embodiment of the present application, the L 14 is a biphenylene group.

[0135] In one embodiment of the present application, the L 14 is a naphthylene group.

[0136] In one embodiment of the present application, Ar 13 and Ar 14may be the same or different and each independently be a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.

[0137] In one embodiment of the present application, Ar 13 and Ar 14 may be the same or different and each independently be a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0138] In one embodiment of the present application, the Ar 13 and Ar 14 may be the same or different and each independently be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted dibenzothiophene group; or a substituted or unsubstituted dibenzofuran group.

[0139] In one embodiment of the present application, the Ar 13 and Ar 14 may be the same or different, and each independently represent a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a fluorenyl group substituted or unsubstituted with one or more selected from the group consisting of a phenyl group and an alkyl group having 1 to 10 carbon atoms; a substituted or unsubstituted dibenzothiophene group; or a substituted or unsubstituted dibenzofuran group.

[0140] In one embodiment of the present application, the Ar 13 and Ar 14may be the same or different and each independently represent a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a fluorenyl group substituted or unsubstituted with one or more selected from the group consisting of a phenyl group and a methyl group; a substituted or unsubstituted dibenzothiophene group; or a substituted or unsubstituted dibenzofuran group.

[0141] In one embodiment of the present application, the Ar 13 and Ar 14 may be the same or different and each independently represent a phenyl group; a biphenyl group; a naphthyl group; a fluorenyl group substituted or unsubstituted with one or more selected from the group consisting of a phenyl group and a methyl group; a substituted or unsubstituted dibenzothiophene group; or a substituted or unsubstituted dibenzofuran group.

[0142] In one embodiment of the present application, c and d in the above formula A-1 may be 0 or 1, respectively.

[0143] In one embodiment of the present application, c is 0.

[0144] In one embodiment of the present application, c is 1.

[0145] In one embodiment of the present application, d is 0.

[0146] In one embodiment of the present application, d is 1.

[0147] In one embodiment of the present application, R 20 ~R 26 may each independently be hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0148] In one embodiment of the present application, the R 20 ~R 26may each independently be hydrogen; deuterium; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0149] In one embodiment of the present application, the R 20 ~R 26 may each independently be hydrogen; deuterium; or a substituted or unsubstituted phenyl group.

[0150] In one embodiment of the present application, the R 20 ~R 26 may each independently be a hydrogen atom or a phenyl group.

[0151] In one embodiment of the present application, the R 20 may be hydrogen; or a phenyl group.

[0152] In one embodiment of the present application, the R 20 is hydrogen.

[0153] In one embodiment of the present application, the R 20 is a phenyl group.

[0154] In one embodiment of the present application, the R 21 is hydrogen.

[0155] In one embodiment of the present application, the R 22 is hydrogen.

[0156] In one embodiment of the present application, the R 23 is hydrogen.

[0157] In one embodiment of the present application, the R 24 is hydrogen.

[0158] In one embodiment of the present application, the R 25 is hydrogen.

[0159] In one embodiment of the present application, the R 26is hydrogen.

[0160] In one embodiment of the present application, X in formula A-5 11 represents O; S; or CRcRd, and Rc and Rd may be the same or different and each independently represent a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0161] In one embodiment of the present application, the X 11 is O; S; or CRcRd, and both Rc and Rd may be methyl groups.

[0162] In one embodiment of the present application, the X 11 is O.

[0163] In one embodiment of the present application, the X 11 is S.

[0164] In one embodiment of the present application, the X 11 is CRcRd, and both Rc and Rd are methyl groups.

[0165] In the case where the heterocyclic compound having the formula A-1 in the formula 1 is used as an organic material in the organic light emitting device, the driving voltage of the organic light emitting device can be further reduced and the organic light emitting device can have higher efficiency, which is believed to be because the heterocyclic compound having the formula A-1 in the formula R1 has faster hole mobility.

[0166] In one embodiment of the present application, there is provided a heterocyclic compound represented by any one of the following compounds:

[0167] [ka] TIFF0007651192000035.tif183161 TIFF0007651192000036.tif202161 TIFF0007651192000037.tif188161 TIFF0007651192000038.tif181161 TIFF0007651192000039.tif203161 TIFF0007651192000040.tif213161 TIFF0007651192000041.tif171161

[0168] In addition, it is possible to synthesize compounds having properties specific to the introduced substituents by introducing various substituents into the structure of Formula 1. For example, it is possible to synthesize materials that satisfy the requirements for each organic layer by introducing into the core structure substituents that are mainly used in hole injection layer materials, hole transport layer materials, light emitting layer materials, electron transport layer materials, and charge generation layer materials used in the manufacture of organic light emitting devices.

[0169] Furthermore, by introducing various substituents into the structure of formula 1, the energy band gap can be finely adjusted, while the properties at the interface between organic substances can be improved, thereby diversifying the uses of the material.

[0170] On the other hand, the heterocyclic compound has a high glass transition temperature (Tg) and therefore has excellent thermal stability, which is an important factor in providing driving stability to the device.

[0171] The heterocyclic compound according to one embodiment of the present application can be produced by a multi-step chemical reaction. Some intermediate compounds can be produced in advance, and the compound of formula 1 can be produced from the intermediate compounds. More specifically, the heterocyclic compound according to one embodiment of the present application can be produced based on the production examples described below.

[0172] Another embodiment of the present application provides an organic light-emitting device including a heterocyclic compound represented by Formula 1. The "organic light-emitting device" can be expressed by terms such as "organic light-emitting diode," "OLED (Organic Light Emitting Diodes)," "OLED device," and "organic electroluminescent device."

[0173] In one embodiment of the present application, there is provided an organic light-emitting device comprising: a first electrode; a second electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein at least one of the organic layers contains a heterocyclic compound represented by Formula 1.

[0174] In one embodiment of the present application, the first electrode may be an anode and the second electrode may be a cathode.

[0175] In yet another embodiment of the present application, the first electrode may be a cathode and the second electrode may be an anode.

[0176] In one embodiment of the present application, the organic light-emitting device may be a blue organic light-emitting device, and the heterocyclic compound according to Formula 1 can be used as a material of the blue organic light-emitting device.

[0177] In yet another embodiment of the present application, the organic light-emitting device may be a green organic light-emitting device, and the heterocyclic compound according to Formula 1 can be used as a material of the green organic light-emitting device.

[0178] In yet another embodiment of the present application, the organic light-emitting device may be a red organic light-emitting device, and the heterocyclic compound according to Formula 1 can be used as a material of the red organic light-emitting device.

[0179] Specific details regarding the heterocyclic compound represented by the formula 1 are as described above.

[0180] The organic light-emitting device of the present application can be manufactured by a typical manufacturing method and material for an organic light-emitting device, except that one or more organic layers are formed using the above-mentioned heterocyclic compound.

[0181] In manufacturing an organic light emitting device, the heterocyclic compound may be formed in an organic layer by a solution coating method as well as a vacuum deposition method, where the solution coating method refers to, but is not limited to, spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc.

[0182] The organic layer of the organic light-emitting device of the present invention may have a single-layer structure, but may have a multi-layer structure in which two or more organic layers are laminated. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as the organic layer. However, the structure of the organic light-emitting device is not limited thereto, and may include a smaller number of organic layers.

[0183] In the organic light emitting device of the present application, the organic material layer includes an emission layer, and the emission layer may include a heterocyclic compound. When the heterocyclic compound is used in the emission layer, a homo (HOMO, highest occupied molecular orbital) and a lumo (LUMO, HOMO, lowest ighest unoccupied molecular orbital) are spatially separated to enable strong charge transfer, so that the organic light emitting device can have excellent driving efficiency and life. The organic light emitting device can have excellent driving, efficiency, and life.

[0184] 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, a hole auxiliary layer, and a hole blocking layer.

[0185] 1 to 3 show examples of the stacking order of electrodes and organic layers of an organic light-emitting device according to one embodiment of the present application. However, these drawings are not intended to limit the scope of the present application, and structures of organic light-emitting devices known in the art are also applicable to the present application.

[0186] 1 shows an organic light emitting device in which an anode 200, an organic layer 300, and a cathode 400 are sequentially stacked on a substrate 100. However, the present invention is not limited to this structure, and an organic light emitting device in which a cathode, an organic layer, and an anode are sequentially stacked on a substrate as shown in FIG.

[0187] Fig. 3 illustrates an example in which the organic layer is multi-layered. The organic light-emitting device according to 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 laminated structure, and the remaining layers except for the emitting layer may be omitted as necessary, and other necessary functional layers may be further added.

[0188] The organic layer containing the compound represented by formula 1 may further contain other materials as necessary.

[0189] In an organic light-emitting device according to one embodiment of the present application, materials other than the compound of Formula 1 are exemplified below, but these are merely illustrative and are not intended to limit the scope of the present application, and may be substituted with materials known in the art.

[0190] The anode material may be a material with a relatively low work function, such as a transparent conductive oxide, a metal, or a conductive polymer. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

[0191] The cathode material may be a material having a relatively low work function, such as a metal, a metal oxide, or a conductive polymer. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; and multilayered materials such as LiF / Al or LiO2 / Al.

[0192] As the hole injection material, a known hole injection material can be used, for example, a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Pat. No. 4,356,429 or a starburst type amine derivative described in the literature [Advanced Material, 6, p. 677 (1994)], for example, tris(4-carbazoyl-9-ylphenyl)amine (TCTA), 4,4',4''-tri[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB), polyaniline / dodecylbenzenesulfonic acid, which is a soluble conductive polymer, or the like can be used. Poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate), Polyaniline / Camphor sulfonic acid or Polyaniline / Poly(4-styrenesulfonate), etc. can be used.

[0193] As the hole transport material, a pyrazoline derivative, an arylamine derivative, a stilbene derivative, a triphenyldiamine derivative, or the like can be used, and a low molecular weight or high molecular weight material can also be used.

[0194] Examples of electron transport materials that can be used include oxadiazole derivatives, anthraquinodimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinodimethane and its derivatives, fluorenone derivatives, diphenyldicyanoethylene and its derivatives, diphenoquinone derivatives, and metal complexes of 8-hydroxyquinoline and its derivatives. Not only low molecular weight materials but also polymeric materials can be used.

[0195] As the electron injection material, for example, LiF is typically used in the art, but the present application is not limited thereto.

[0196] The light-emitting material may be a red, green or blue light-emitting material, and if necessary, two or more light-emitting materials may be mixed and used. In this case, two or more light-emitting materials may be vapor-deposited as separate sources, or may be premixed and vapor-deposited as one source. The light-emitting material may be a fluorescent material or a phosphorescent material. The light-emitting material may be a material that emits light by combining holes and electrons injected from the anode and cathode, respectively, or a material in which both the host material and the dopant material are involved in light emission may be used.

[0197] When the hosts of the light-emitting materials are mixed, the hosts may be of the same series or different series. For example, two or more of either n-type host materials or p-type host materials may be selected and used as the host material of the light-emitting layer.

[0198] In the organic light-emitting device of the present application, the organic layer includes a light-emitting layer, and the light-emitting layer can include a heterocyclic compound as a host material for light-emitting materials.

[0199] In the organic light-emitting device of the present application, the light-emitting layer may contain two or more host materials, and at least one of the host materials may contain the heterocyclic compound as a host material for a light-emitting material.

[0200] In the organic light-emitting device of the present application, the light-emitting layer may be used by pre-mixing two or more host materials, and at least one of the two or more host materials may contain the heterocyclic compound as a host material of the light-emitting material.

[0201] The term "pre-mixed" means that the light-emitting layer is prepared by mixing two or more host materials in a single source prior to deposition of the materials into the organic layers.

[0202] In the organic light-emitting device of the present application, the light-emitting layer can include two or more host materials, each of which includes one or more p-type host materials and one or more n-type host materials, and at least one of the host materials can be included as the host material of the heterocyclic light-emitting material. In this case, the organic light-emitting device can have excellent driving, efficiency, and life.

[0203] In the organic light-emitting device of the present application, the light-emitting layer may contain the heterocyclic compound and any one of the following heterocyclic compounds 1-1 to 1-14.

[0204] [ka] In one embodiment of the present application, the heterocyclic compound represented by the above formula 1 and any one of the heterocyclic compounds 1-1 to 1-14 can be used as a host material.

[0205] In one embodiment of the present application, there is provided a composition for an organic layer of an organic light-emitting device, comprising a heterocyclic compound represented by the above formula 1 and any one of the following heterocyclic compounds 1-1 to 1-14.

[0206] [ka] The weight ratio of the heterocyclic compound represented by formula 1 to any one of the heterocyclic compounds 1-1 to 1-14 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.

[0207] The organic light emitting device according to one embodiment of the present application may be a front-emitting, back-emitting, or dual-emitting type depending on the materials used.

[0208] The heterocyclic compound according to one embodiment of the present application can also function in organic electronic devices such as organic solar cells, organic photoreceptors, and organic transistors based on the same principle as that applied to organic light-emitting devices. EXAMPLES

[0209] The present specification will be described in more detail below through embodiments, which are merely for illustrating the present application and are not intended to limit the scope of the present application.

[0210] <Production Example> <Production Example 1> Production of Compound 1 [ka]

[0211] 1) Preparation of Compound C-2 100g (448.29mmol) of 1-bromonaphthalen-2-ol, 85.98g (493.12mmol) of (2-chloro-6-fluorophenyl)boronic acid, 425.9g (22.41mmol) of Pd(PPh), and 95.03g (896.58mmol) of Na2CO3 were dissolved in 1L / 200mL / 200mL of Toluene / Ethanol / H2O and refluxed for 4 hours. After the reaction was completed, the mixture was extracted with distilled water and dichloromethane (DCM) at room temperature, and the organic layer was dried with MgSO4 and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:HeX=1:1) to obtain 48.9 g (40%) of the target compound C-1.

[0212] 2) Preparation of Compound C-1 Compound C-2 (49g, 179.68mmol) and Cs2CO3 (146.36g, 449.21mol) were dissolved in DMA (dimetylacetamide) (400mL) and then refluxed for 2 hours. After the reaction was completed, the salt was filtered at room temperature and the solvent was removed using a rotary evaporator. The reaction product was purified with DCM / MeOH to obtain the target compound C-1 (27.24g, 60%).

[0213] 3) Preparation of Compound C 27 g (106.84 mmol) of compound C-1 was dissolved in 300 mL of chloroform (CHCL3) at room temperature, and then Br2 was added dropwise to react. After the reaction was completed, the product was recrystallized from methanol to obtain 26.93 g (76%) of the target compound C.

[0214] [ka]

[0215] 4) Preparation of Compound 1-2 Compound 1-3 (compound C) 10.0g (30.15mmol), diphenylamine 5.1g (30.15mmol), Pd2(dba) 31.38g (1.51mmol), P(t-Bu) 31.22g (3.02mmol), NaOtBu 5.67g (60.32mmol) were dissolved in Toluene 100mL and refluxed for 2 hours. After the reaction was completed, distilled water and DCM were added at room temperature for extraction, the organic layer was dried with MgSO4, and the solvent was removed with a rotary evaporator. The reactant was purified by column chromatography (DCM:HeX=1:3) to obtain 7.59g (60%) of the target compound 1-2.

[0216] 5) Preparation of Compound 1-1 Compound 1-2 7.59g (18.08mmol), bis(pinacolato)diboron (4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi-(1,3,2-dioxaborolane) 5.97g (23.5mmol), Pd2(dba) 30.83g (0.903mmol), Xphos 0.86g (1.81mmol), KOAc 3.55g (36.15mmol) were dissolved in 1,4-dioxane 80mL and refluxed for 12 hours. After the reaction was completed, it was extracted with distilled water and DCM at room temperature, and the organic layer was dried with MgSO4 and the solvent was removed with a rotary evaporator. The reactant was purified by column chromatography (DCM:HeX=1:2) to obtain 4.81g (52%) of the target compound 1-1.

[0217] 6) Preparation of Compound 1 Compound 1-1 4.81g (9.41mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine 2.52g (9.41mmol), Pd(pph3) 40.54g (0.47mmol), K2CO3 2.6g (18.81mmol) were dissolved in 1,4-Dioxane / H2O 50mL / 10mL and then refluxed for 3 hours. After the reaction was completed, the obtained solid was filtered, washed with distilled water and dried. The dried solid was dissolved by boiling in DCB, purified with silica, and the solvent was removed by rotary evaporator. Recrystallization with acetone gave the target compound 1 3.25g (56%).

[0218] The target compound was synthesized in the same manner as in Preparation Example 1, except that in Preparation Example 1, intermediate A-1 in Table 1 below was used instead of diphenylamine, and intermediate B-1 in Table 1 below was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0219] [Table 1] TIFF0007651192000047.tif201161 TIFF0007651192000048.tif202161 TIFF0007651192000049.tif201161 TIFF0007651192000050.tif178161 TIFF0007651192000051.tif182161 TIFF0007651192000052.tif177161 TIFF0007651192000053.tif95161

[0220] <Production Example 2> Production of Compound 13 [ka]

[0221] 1) Preparation of compound 13-3 Compound C 10.0g (30.15mmol), bis(pinacolato)diboron 9.2g (36.2mmol), Pd(dppf)Cl2 1.1g (1.51mmol), KOAc 5.68g (60.32mmol) were dissolved in 1,4-dioxane 100mL and refluxed for 2 hours. After the reaction was completed, the mixture was extracted with distilled water and DCM at room temperature, the organic layer was dried with MgSO4, and the solvent was removed with a rotary evaporator. The reactant was purified by column chromatography (DCM:HeX=1:2) to obtain 6.97g (61%) of the target compound 13-3.

[0222] 2) Preparation of Compound 13-2 Compound 13-3 6.97g (18.41mmol), 4-bromo-N,N-diphenylaniline 5.97g (18.41mmol), Pd(pph3) 41.06g (9.2mmol), K2CO3 5.09g (36.81mmol) were dissolved in 1,4-Dioxane / H2O 80mL / 12mL and refluxed for 3 hours. After the reaction was completed, it was extracted with distilled water and DCM at room temperature, the organic layer was dried with MgSO4, and the solvent was removed with a rotary evaporator. The reaction product was purified by column chromatography (DCM:HeX=1:3) to obtain 4.75g (52%) of the target compound 13-2.

[0223] 3) Preparation of Compound 13-1 Compound 13-2 4.75g (9.58mmol), bis(pinacolato)diboron (4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi-(1,3,2-dioxaborolane) 3.16g (12.45mmol), Pd2(dba) 30.44g (0.48mmol), Xphos 0.46g (0.96mmol), KOAc 1.88g (19.15mmol) were dissolved in 1,4-dioxane 50mL and refluxed for 12 hours. After the reaction was completed, it was extracted with distilled water and DCM at room temperature, the organic layer was dried with MgSO4, and the solvent was removed with a rotary evaporator. The reaction product was purified by column chromatography (DCM:HeX=1:2) to obtain 4.28g (76%) of the target compound 13-1.

[0224] 4) Preparation of Compound 13 Compound 13-1 4.28g (7.28mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine 1.95g (7.28mmol), Pd(pph3) 40.42g (0.36mmol), and K2CO3 2.01g (14.57mmol) were dissolved in 1,4-Dioxane / H2O 50mL / 10mL and then refluxed for 3 hours. After the reaction was completed, the obtained solid was filtered, washed with distilled water and dried. The dried solid was dissolved in DCB by boiling, purified with silica, and the solvent was removed by rotary evaporator. Recrystallization with acetone gave the target compound 13 2.93g (58%).

[0225] The target compound was synthesized in the same manner as in Production Example 2, except that Intermediate A-2 in Table 2 below was used instead of 4-bromo-N,N-diphenylaniline and Intermediate B-2 in Table 2 below was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine in Production Example 2.

[0226] [Table 2] TIFF0007651192000056.tif189161 TIFF0007651192000057.tif189161 TIFF0007651192000058.tif183161 TIFF0007651192000059.tif200161 TIFF0007651192000060.tif96161

[0227] <Production Example 3> Production of Compound 145 [ka]

[0228] 1) Preparation of compound 145-3 Compound C-1 10g (39.57mmol), bis(pinacolato)diboron (4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi-(1,3,2-dioxaborolane) 12.06g (47.49mmol), Pd2(dba) 31.81g (1.98mmol), Xphos 1.89g (3.96mmol), and KOAc 7.77g (79.15mmol) were dissolved in 1,4-dioxane. After dissolving in 100mL, it was refluxed for 12 hours. After the reaction was completed, it was extracted with distilled water and DCM at room temperature, and the organic layer was dried with MgSO4, and the solvent was removed with a rotary evaporator. The reactant was purified by column chromatography (DCM:HeX=1:2) to obtain the target compound 145-3 (8.58g, 63%).

[0229] 2) Preparation of Compound 145-2 Compound 145-3 8.58g (24.93mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine 7.34g (27.42mmol), Pd(pph3) 41.44g (1.25mmol), K2CO3 6.89g (49.85mmol) were dissolved in 1,4-Dioxane / H2O 100mL / 20mL and then refluxed for 3 hours. After the reaction was completed, the obtained solid was filtered, washed with distilled water and dried. The dried solid was dissolved in DCB by boiling and purified with silica, and the solvent was removed by rotary evaporator. The target compound 145-2 was obtained by recrystallization with acetone 9.19g (82%).

[0230] 3) Preparation of Compound 145-1 Compound 145-2 (9.19g, 20.44mmol) was dissolved in THF (120ml) under nitrogen substitution, and the temperature was lowered to -78°C. 2.5M n-BuLi (8.59ml, 21.47mmol) was added dropwise, and the temperature was raised to room temperature and reacted for 1 hour. After lowering the temperature to -78°C again, B(OMe) (32.74mL, 24.53mmol, d:0.932g / ml) was added dropwise, and the temperature was raised to room temperature and reacted for 1 hour. After the reaction was completed, the reaction was terminated with MeOH, purified with silica, and the solvent was removed with a rotary evaporator. The target compound 145-1 was obtained as 5.24g (52%) by recrystallization with EA and Hex.

[0231] 4) Preparation of Compound 145 Compound 145-1 5.24g (10.62mmol), 4-bromo-N,N-diphenylaniline 3.79g (11.68mmol), Pd(pph3) 40.61g (0.53mmol), and K2CO3 2.94g (21.24mmol) were dissolved in 1,4-Dioxane / H2O 50mL / 10mL, and then refluxed for 3 hours. After the reaction was completed, the obtained solid was filtered, washed with distilled water, and dried. The dried solid was dissolved in DCB by boiling and purified with silica, and the solvent was removed by rotary evaporator. Recrystallization with acetone gave the target compound 145 2.58g (35%).

[0232] The target compound was synthesized in the same manner as in Production Example 3, except that in Production Example 3, Intermediate A-3 in Table 3 below was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine and Intermediate B-3 in Table 3 below was used instead of 4-bromo-N,N-diphenylaniline.

[0233] [Table 3] JPEG0007651192000063.jpg211161 JPEG0007651192000064.jpg154161 JPEG0007651192000065.jpg123161

[0234] The compounds described in the present specification were produced in the same manner as in the above-mentioned production examples, and the synthesis confirmation results of the produced compounds are shown in the following Tables 4 and 5. 1 H NMR(CDCL 3、 The values ​​are measured using a field desorption mass spectrometry (FD-MS), and Table 5 below shows the values ​​measured using a field desorption mass spectrometry (FD-MS).

[0235] [Table 4] TIFF0007651192000067.tif229165 TIFF0007651192000068.tif229165 TIFF0007651192000069.tif230165 TIFF0007651192000070.tif230165 TIFF0007651192000071.tif229165 TIFF0007651192000072.tif37165

[0236] [Table 5] TIFF0007651192000074.tif230161 TIFF0007651192000075.tif230161 TIFF0007651192000076.tif230161 TIFF0007651192000077.tif230161 TIFF0007651192000078.tif230161 TIFF0007651192000079.tif230161 TIFF0007651192000080.tif230161 TIFF0007651192000081.tif230161 TIFF0007651192000082.tif60161

[0237] [Experimental Example] <Experimental Example 1> 1) Preparation of organic light-emitting device (red host) A glass substrate coated with a thin film of indium tin oxide (ITO) to a thickness of 1,500 Å was ultrasonically cleaned in distilled water. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UVO for 5 minutes using UV in a UV cleaner. The substrate was then transferred to a plasma cleaner (PT) and plasma treated in a vacuum state to remove the ITO work function and residual film, and then transferred to a thermal evaporation device for organic deposition.

[0238] 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).

[0239] An emitting layer was formed thereon by thermal vacuum deposition as follows: The emitting layer was formed by depositing 500 Å of the following compound A as a host and red phosphorescent dopant (piq)2(Ir)(acac) doped with 3 wt% (piq)2(Ir)(acac). Then, 60 Å of BCP was deposited as a hole blocking layer, and 200 Å of Alq3 was deposited on top of that as an electron transport layer.

[0240] Finally, lithium fluoride (LiF) was deposited on the electron transport layer to a thickness of 10 Å to form an electron injection layer, and then an aluminum (Al) cathode was deposited on the electron injection layer to a thickness of 1,200 Å to form a cathode, thereby fabricating an organic light emitting device (Comparative Example 1).

[0241] On the other hand, all organic compounds required for OLED device production are 10- 6 ~10- 8 It was purified by vacuum sublimation under torr and used for OLED fabrication.

[0242] Organic light-emitting devices of Comparative Examples 2 to 4 and Examples 1 to 65 were additionally prepared in the same manner, except that the compounds shown in Table 6 below were used instead of Compound A used as the host of the light-emitting layer in the manufacturing process of the organic light-emitting device of Experimental Example 1.

[0243] Specifically, the compounds used as hosts in the light-emitting layers in Examples 1 to 65 and Comparative Examples 1 to 4 are as shown in Table 6 below.

[0244] At this time, compounds A to D of Comparative Examples 1 to 4 in Table 6 below are as follows.

[0245] [ka]

[0246] 2) Driving voltage and luminous efficiency of organic light-emitting devices The electroluminescence (EL) characteristics of the organic electroluminescent devices of Examples 1 to 65 and Comparative Examples 1 to 4 prepared as described above were measured using M7000 from Mac Science Co., Ltd. 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 Co., Ltd. 2 When T 90 was measured.

[0247] The measured characteristics of the organic light-emitting device of the present invention are shown in Table 6 below.

[0248] [Table 6] TIFF0007651192000085.tif232169 TIFF0007651192000086.tif151169

[0249] From the experimental example 1, it was confirmed that the driving voltage and efficiency can be improved when the heterocyclic compound of the formula 1 is used as a host for the organic layer, particularly the light-emitting layer, of an organic light-emitting device. Specifically, in the case of the examples 1 to 65 using the heterocyclic compound of the formula 1, as compared with the comparative examples 1 to 4, the resonance effect increases as the number of benzene rings in the central structure increases, and it was confirmed that it is suitable as a red host. In addition, it has a donor with good hole transporting ability and an acceptor with good electron transporting ability simultaneously in one molecule, and has a steric configuration by fixing a substituent to the 11th position of naphthobenzofuran, and the homo (HOMO, Highest Occupied Molecular Orbital) and the lumo (HOMO, Lowest ighest Unoccupied Molecular Orbital) are spatially separated, enabling strong charge transfer, so that it is confirmed that high efficiency can be expected when used as an organic material in an organic light-emitting device.

[0250] In addition, by comparing Examples 1 to 57 with Examples 58 to 65, it was confirmed that the driving voltage is relatively lower when the hole unit corresponding to R1 in Formula 1 is an amine group than when it is a carbazole group. This is believed to be because when the hole unit corresponding to R1 is an amine group, the hole mobility is relatively faster than when it is a carbazole group, and light can be emitted at a low voltage.

[0251] <Experimental Example 2> 1) Preparation of organic light-emitting device (red host) A glass substrate coated with a thin film of indium tin oxide (ITO) to a thickness of 1,500 Å was ultrasonically cleaned in distilled water. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UVO for 5 minutes using UV in a UV cleaner. The substrate was then transferred to a plasma cleaner (PT) and plasma treated in a vacuum state to remove the ITO work function and residual film, and then transferred to a thermal evaporation device for organic deposition.

[0252] 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'-Dinaphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine), were formed on the ITO transparent electrode (anode).

[0253] An emitting layer was formed thereon by thermal vacuum deposition as follows: The emitting layer was formed by depositing heterocyclic compound 5 of the present invention as a first host and compound 1-1 as a second host as one supply source, and by doping the host with 3 wt% of (piq)2(Ir)(acac) as a red phosphorescent dopant (piq)2(Ir)(acac) and depositing it to a thickness of 500 Å. Then, BCP was deposited to a thickness of 60 Å as a hole blocking layer, and Alq3 was deposited to a thickness of 200 Å as an electron transport layer thereon.

[0254] Finally, lithium fluoride (LiF) was deposited on the electron transport layer to a thickness of 10 Å to form an electron injection layer, and then an aluminum (Al) cathode was deposited on the electron injection layer to a thickness of 1,200 Å to form a cathode, thereby fabricating an organic light emitting device (Example 66).

[0255] On the other hand, all organic compounds required for OLED device production are 10- 6 ~10- 8 It was purified by vacuum sublimation under torr and used for OLED fabrication.

[0256] Organic light-emitting devices of Examples 66 to 113 were additionally prepared in the same manner, except that the compounds shown in Table 7 below were used instead of Compound 1-1 used as the second host in the light-emitting layer in the manufacturing process of the organic light-emitting device of Experimental Example 2.

[0257] Specifically, the compounds used as the first host and the second host in the emitting layer in Examples 66 to 113 are as shown in Table 7 below.

[0258] 2) Driving voltage and luminous efficiency of organic light-emitting devices The electroluminescence (EL) characteristics of the organic light emitting devices of Examples 66 to 113 prepared as described above were measured using the M7000 from Mac Science Co., Ltd., and the measurement results were used to measure the reference luminance of 6,000 cd / m2 or less through a lifespan measuring device (M6000) manufactured by Mac Science Co., Ltd. 2 When T 95 was measured.

[0259] The measured characteristics of the organic light-emitting device of the present invention are shown in Table 7 below.

[0260] In this case, compounds 1-1 to 1-14 in the following Table 7 are as follows: Compounds 1-1 to 1-14 are p-Host (p-type host) compounds having excellent hole transporting ability.

[0261] [ka]

[0262] [Table 7] TIFF0007651192000089.tif177165

[0263] From the above Experimental Example 2, it was confirmed that when the heterocyclic compound of the present invention is used as the first host in the organic layer, particularly the light-emitting layer, of an organic light-emitting device, and a specific compound having excellent hole transporting ability is used as the second host, the driving voltage and efficiency can be improved. Specifically, it was confirmed that when the compounds 1-1 to 1-14 having hole transporting ability are used in combination with the heterocyclic compound of the present invention, the degradation phenomenon caused by the accumulation of electrons generated from the heterocyclic compound of the present invention can be reduced, and the problem of life can be improved.

[0264] <Experimental Example 3> 1) Preparation of organic light-emitting device (red host) A glass substrate coated with a thin film of indium tin oxide (ITO) to a thickness of 1,500 Å was ultrasonically cleaned in distilled water. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UVO for 5 minutes using UV in a UV cleaner. The substrate was then transferred to a plasma cleaner (PT) and plasma treated in a vacuum state to remove the ITO work function and residual film, and then transferred to a thermal evaporation device for organic deposition.

[0265] 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).

[0266] An emitting layer was formed thereon by thermal vacuum deposition as follows: The emitting layer was formed by depositing heterocyclic compound 14 of the present invention as a first host and compound 2-1 as a second host as one supply source, and was deposited to a thickness of 500 Å by doping the host with 3 wt% of (piq)2(Ir)(acac) using red phosphorescent dopant (piq)2(Ir)(acac). Then, 60 Å of BCP was deposited as a hole blocking layer, and 200 Å of Alq3 was deposited thereon as an electron transport layer.

[0267] Finally, lithium fluoride (LiF) was deposited on the electron transport layer to a thickness of 10 Å to form an electron injection layer, and then an aluminum (Al) cathode was deposited on the electron injection layer to a thickness of 1,200 Å to form a cathode, thereby fabricating an organic light emitting device (Example 114).

[0268] On the other hand, all organic compounds required for OLED device production are 10- 6 ~10- 8 It was purified by vacuum sublimation under torr and used for OLED fabrication.

[0269] In the manufacturing process of the organic light-emitting device of Experimental Example 3, except that the compounds shown in Table 8 below were used instead of Compound 14 and Compound 2-1 used as the first host of the light-emitting layer, organic light-emitting devices of Examples 114 to 153 were additionally manufactured in the same manner.

[0270] Specifically, the compounds used as the first host and the second host in the emitting layer in Examples 114 to 153 are as shown in Table 8 below.

[0271] 2) Driving voltage and luminous efficiency of organic light-emitting devices The electroluminescence (EL) characteristics of the organic light emitting devices of Examples 114 to 153 prepared as described above were measured using the M7000 from Mac Science Co., Ltd., and the measurement results were used to measure the reference luminance of 6,000 cd / m2 through a lifespan measuring device (M6000) manufactured by Mac Science Co., Ltd. 2 When T 95 was measured.

[0272] The measured characteristics of the organic light-emitting device of the present invention are shown in Table 8 below.

[0273] In this case, compounds 2-1 to 2-4 in the following Table 8 are as follows: Compounds 2-1 to 2-4 below are n-host (n-type host) compounds with excellent electron transport ability.

[0274] [ka]

[0275] [Table 8] TIFF0007651192000092.tif194165

[0276] From the above Experimental Example 3, it was confirmed that the life of the device can be improved when the heterocyclic compound of the present invention is used as the first host in the organic layer of an organic light-emitting device, particularly in the light-emitting layer, and a specific compound having excellent electron transport ability is used as the second host. Specifically, it was confirmed that when the compounds 2-1 to 2-4 having electron transport ability are used in combination with the heterocyclic compound of the present invention, the charge balance in the light-emitting layer is maximized, thereby improving the light-emitting characteristics. [Explanation of symbols]

[0277] 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 formulas 2-1 to 2-6 and 3-1 to 3-6: 【Chemistry 49】 【Chemistry 50】 【Chemistry 51】 【Chemistry 52】 【Chemistry 53】 【Chemical 54】 【Chemistry 55】 【Chemistry 56】 【Chemistry 57】 【Chemistry 58】 【Chemistry 59】 【Chemistry 60】 In the formulas 2-1 to 2-6 and 3-1 to 3-6, L １ and L ２ are the same or different and each independently represent a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms, X is O; S; or NRa; Y 11 to Y 15 each represent CRb, and when CRb is 2 or more, each Rb is the same or different; R １ is represented by any one of the following formulas A-1 to A-5, wherein Ra is a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; Rb is selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms or a substituted or unsubstituted heterocycle having 2 to 60 carbon atoms; m and n are each independently an integer of 0 to 3, and when m and n are each 2 or more, the substituents in parentheses are the same or different. 【Chemistry 61】 【Chemistry 62】 【Chemistry 63】 【Chemistry 64】 【Chemistry 65】 In the formulae A-1 to A-5, L 13 and L 14 are the same or different and each independently represents a direct bond; a substituted or unsubstituted arylene group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms; Ar 13 and Ar 14 are the same or different and each independently represents a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms; R 20 to R 26 are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms; X 11 is O; S; or CRcRd, where Rc and Rd may be the same or different and each independently represent a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; c and d are each 0 or 1; 【Chemistry 46】 is any one of L of the formulas 2-1 to 2-6 and 3-1 to 3-6. １ This means the position at which the molecule binds to the

2. The "substituted or unsubstituted" means that the heterocyclic compound according to claim 1 is substituted or unsubstituted with one or more substituents selected from the group consisting of a linear or branched alkyl group having 1 to 60 carbon atoms; a linear or branched alkenyl group having 2 to 60 carbon atoms; a linear or branched alkynyl group having 2 to 60 carbon atoms; a monocyclic or polycyclic cycloalkyl group having 3 to 60 carbon atoms; a monocyclic or polycyclic heterocycloalkyl group having 2 to 60 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 60 carbon atoms; a monocyclic or polycyclic heteroaryl group having 2 to 60 carbon atoms; a silyl group; a phosphine oxide group; and an amine group, or is substituted or unsubstituted with a substituent in which two or more substituents selected from the above-mentioned exemplary substituents are linked.

3. The heterocyclic compound according to claim 1, wherein the formulas 2-1 to 2-6 and 3-1 to 3-6 are represented by any one of the following compounds: 【Chemistry 67】 【change】 【change】 【change】 【change】 【change】 【change】 【change】

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

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

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

7. The organic light-emitting element according to claim 6 , wherein the light-emitting layer comprises two or more host materials, and at least one of the host materials is the heterocyclic compound.

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

9. A composition for an organic layer of an organic light-emitting device, comprising the heterocyclic compound represented by any one of formulas 2-1 to 2-6 and 3-1 to 3-6 according to claim 1 and any one of heterocyclic compounds 1-1 to 1-14 below. 【Chemistry 68】

10. The composition for an organic layer of an organic light-emitting device according to claim 9, wherein a weight ratio of the heterocyclic compound represented by any one of formulas 2-1 to 2-6 and 3-1 to 3-6 to any one of heterocyclic compounds 1-1 to 1-14 in the composition is 1:10 to 10:1.

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