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 specification claims the benefit of the filing date of Korean Patent Application No. 10-2019-0175840, filed with the Korean Intellectual Property Office on December 27, 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] 2. Description of the Related Art An electroluminescent device is a type of self-luminous display device, and has the advantages of a wide viewing angle, excellent contrast, and fast response speed.

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

[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 can act as 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 can inject holes, transport holes, block electrons, transport electrons, inject electrons, etc.

[0006] In order to improve the performance, lifetime or efficiency of organic light emitting devices, there is a continuing need to develop materials for organic thin films. [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 an organic light-emitting device. [Means for solving the problem]

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

[0010] In the above Chemical Formula 1, L is 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; or S; N-het is a substituted or unsubstituted monocyclic or polycyclic heterocyclic group containing one or more N; Ar is a substituted or unsubstituted amine group selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; or a substituted or unsubstituted amine group substituted or unsubstituted with one or more groups selected from the group consisting of 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; R p is hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroaryl group having 6 to 40 carbon atoms, a is an integer of 0 to 3, and when a is 2 or more, the substituents in the parentheses are the same or different, b is an integer of 0 to 4, and when b is 2 or more, the substituents in the parentheses are the same or different from each other, p is an integer of 0 to 6, and when p is 2 or more, the substituents in the parentheses are the same or different.

[0011] Also, 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 comprises a heterocyclic compound represented by Chemical Formula 1.

[0012] Finally, one embodiment of the present application provides a composition for an organic layer of an organic light-emitting device, comprising two or more of the heterocyclic compounds represented by Chemical Formula 1. Effect of the Invention

[0013] The heterocyclic compounds described herein can be used as materials for the organic layers of organic light-emitting devices, and can act as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, etc. in the organic light-emitting devices.

[0014] Specifically, when the heterocyclic compound represented by Chemical Formula 1 is used in the 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. [Brief description of the drawings]

[0015] [Figure 1] 1 is a diagram illustrating an example of a layered structure of an organic light-emitting device according to an embodiment of the present application. [Diagram 2] 1 is a diagram illustrating an example of a layered structure of an organic light-emitting device according to an embodiment of the present application. [Diagram 3] 1 is a diagram illustrating an example of a layered structure of an organic light-emitting device according to an embodiment of the present application. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0016] This specification will be explained in more detail below.

[0017] 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.

[0018] 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.

[0019] 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 in which two or more substituents selected from the above-mentioned exemplary substituents are linked.

[0020] More specifically, in this specification, "substituted or unsubstituted" may mean being substituted or unsubstituted with one or more substituents selected from the group consisting of monocyclic or polycyclic aryl groups having 6 to 60 carbon atoms; or monocyclic or polycyclic heteroaryl groups having 2 to 60 carbon atoms.

[0021] In this specification, the halogen may be fluorine, chlorine, bromine or iodine.

[0022] 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, a heptyl group, Examples of aryl groups include, but are not limited to, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, and 5-methylhexyl.

[0023] 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.

[0024] 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.

[0025] 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, and the like.

[0026] 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 linked 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 of 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.

[0027] In this specification, the heterocycloalkyl group contains O, S, Se, N or Si as a heteroatom, contains 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 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, more specifically 3 to 20.

[0028] 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 the 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 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 thereto.

[0029] 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 independently may 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.

[0030] In this specification, a silyl group is a substituent that contains Si and is directly linked to the Si atom as a radical, and is represented by -SiR104R105R106, where R104 to R106 may be the same or different and each may be independently a substituent consisting of at least one of hydrogen, deuterium, a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a cycloalkyl group, an aryl group, and a heterocyclic group. Specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.

[0031] As used herein, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

[0032] 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 include 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 include any one of the groups of the following structural formulas. [ka]

[0033] 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 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, 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 triazolyl group, a azainyl 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, Benzocarbazolyl 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, pheno Examples of such alkyl groups include, but are not limited to, thiathiazinyl, 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.

[0034] As used herein, the amine group is a monoalkylamine group; a monoarylamine group; a monoheteroarylamine group; -NH 2The amine group may be selected from the group consisting of 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.

[0035] In this specification, the arylene group means an aryl group having two bonding positions, i.e., a divalent group. The above-mentioned explanation of the aryl group may be applied to these groups, except that they are each divalent groups. In addition, the heteroarylene group means a heteroaryl group having two bonding positions, i.e., a divalent group. The above-mentioned explanation of the heteroaryl group may be applied to these groups, except that they are each divalent groups.

[0036] In this specification, "adjacent" groups may refer to a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent sterically closest to the substituent, or another substituent substituted on the atom on which the substituent is substituted. For example, two substituents substituted at the ortho positions on a benzene ring and two substituents substituted on the same carbon atom on an aliphatic ring can be interpreted as "adjacent" groups to each other.

[0037] In this specification, when "no substituent is shown in the chemical formula or compound structure," it means that a hydrogen atom is bonded to the carbon atom. However, deuterium (2 H, Deuterium) is an isotope of hydrogen, so some hydrogen atoms may be deuterium.

[0038] In one embodiment of the present application, "when no substituent is shown in the chemical formula or compound structure", it may mean that all positions available as a substituent are hydrogen or deuterium. That is, in the case of deuterium, which is an isotope of hydrogen, some hydrogen atoms may be deuterium, which is an isotope of hydrogen, and in this case, the content of deuterium may be 0% to 100%.

[0039] In one embodiment of the present application, in the case where "substituents are not shown in the chemical formula or compound structure", when deuterium is not clearly excluded, for example, when the deuterium content is 0%, the hydrogen content is 100%, and all substituents are hydrogen, hydrogen and deuterium may be used together in the compound.

[0040] In one embodiment of the present application, deuterium is one of the isotopes of hydrogen and is an element having a deuteron consisting of one proton and one neutron as an atomic nucleus, and may be represented as hydrogen-2, and its atomic symbol may be D or 2H.

[0041] In one embodiment of the present application, isotopes, meaning atoms with the same atomic number (Z) but different mass numbers (A), can be interpreted as elements with the same number of protons but different numbers of neutrons.

[0042] 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.

[0043] That is, in one example: [ka] In a phenyl group represented by the formula, the deuterium content is 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). In other words, a phenyl group having a deuterium content of 20% may be represented by the following structural formula. [ka]

[0044] In addition, in one embodiment of the present application, a "phenyl group having a deuterium content of 0%" may mean a phenyl group that does not contain a deuterium atom, that is, a phenyl group that has five hydrogen atoms.

[0045] In one embodiment of the present application, there is provided a heterocyclic compound represented by the following Chemical Formula 1: [ka]

[0046] In the above Chemical Formula 1, L is 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; or S; N-het is a substituted or unsubstituted monocyclic or polycyclic heterocyclic group containing one or more N; Ar is a substituted or unsubstituted amine group selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; or a substituted or unsubstituted amine group substituted or unsubstituted with one or more groups selected from the group consisting of 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; R pis hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroaryl group having 6 to 40 carbon atoms, a is an integer of 0 to 3, and when a is 2 or more, the substituents in the parentheses are the same or different, b is an integer of 0 to 4, and when b is 2 or more, the substituents in the parentheses are the same or different from each other, p is an integer of 0 to 6, and when p is 2 or more, the substituents in the parentheses are the same or different.

[0047] The heterocyclic compound represented by Chemical Formula 1 has high thermal stability, the N-het is linked without a linker, and has an appropriate molecular weight and band gap. When such a compound is used in the light-emitting layer of an organic light-emitting device, it helps prevent the loss of electrons and holes and forms an effective recombination zone of electrons and holes. When the recombination efficiency increases, the current efficiency increases. Therefore, when the heterocyclic compound represented by Chemical Formula 1 is used as an organic material in an organic light-emitting device, the organic light-emitting device can be expected to have high efficiency and long life.

[0048] In one embodiment of the present application, the above-mentioned Chemical Formula 1 may be represented by any one of the following Chemical Formulae 1-1 to 1-3. [ka] [ka] [ka]

[0049] In the above Chemical Formulae 1-1 to 1-3, the definitions of the respective substituents are the same as those in Chemical Formula 1.

[0050] In one embodiment of the present application, L in Chemical Formula 1 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.

[0051] In another embodiment, L 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.

[0052] In still another embodiment, the L 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.

[0053] In still another embodiment, the L may be a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted naphthylene group; or a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms.

[0054] In yet another embodiment, L can be a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted naphthalene group.

[0055] In yet another embodiment, L may be a direct bond; a phenylene group; or a naphthalene group.

[0056] In yet another embodiment, L is a direct bond.

[0057] In yet another embodiment, L is a phenylene group.

[0058] In yet another embodiment, L is a naphthylene group.

[0059] In one embodiment of the present application, X in the above formula 1 may be O; or S.

[0060] In one embodiment of the present application, said X is O.

[0061] In one embodiment of the present application, said X is S.

[0062] In one embodiment of the present application, N-het in the above Chemical Formula 1 may be a substituted or unsubstituted monocyclic or polycyclic heterocyclic group containing one or more N atoms.

[0063] In another embodiment, the N-het may be a substituted or unsubstituted monocyclic or polycyclic heterocyclic group containing 1 to 3 N's.

[0064] In yet another embodiment, the N-het is unsubstituted or substituted with one or more substituents selected from the group consisting of aryl groups having 6 to 60 carbon atoms and heteroaryl groups having 2 to 60 carbon atoms, and may be a monocyclic or polycyclic heterocyclic group containing one or more N and having 2 to 60 carbon atoms.

[0065] In yet another embodiment, the N-het is unsubstituted or substituted with one or more substituents selected from the group consisting of aryl groups having 6 to 60 carbon atoms and heteroaryl groups having 2 to 60 carbon atoms, and may be a monocyclic or polycyclic heterocyclic group containing 1 to 3 N and having 2 to 60 carbon atoms.

[0066] In yet another embodiment, the N-het may be represented by formula A: [ka]

[0067] In the above chemical formula A, * indicates the position where the N-het is bonded to the above-mentioned Chemical Formula 1, Y 1 ~Y 5 are the same or different, and each independently represents N or CRa; Y 1 ~Y 5At least one of the CRa is N, and when CRa is 2 or more, each Ra is the same or different, The Ra 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 may 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.

[0068] In one embodiment of the present application, the chemical formula A may be represented by any one of the following chemical formulae A-1 to A-7. [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0069] In the above chemical formulas A-1 to A-7, * indicates the position where the N-het is bonded to the above-mentioned Chemical Formula 1, Z 1 ~Z 16 are the same or different and each independently represents N or CH; Z 1 ~Z 3At least one of them is N, and Z 4 ~Z 6 At least one of them is N, and Z 7 and Z 8 At least one of them is N, and Z 9 and Z 10 At least one of them is N, and Z 11 and Z 12 At least one of them is N, and Z 13 and Z 14 At least one of them is N, and Z 15 and Z 16 At least one of them is N, L 1 ~L 9 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, Ar 1 ~Ar 9 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, X 1 ~X 3 are the same or different and each independently represents O; or S; q1 to q9 each independently represent an integer of 0 to 2, and when each of q1 to q9 is 2, the substituents in the parentheses are the same or different from each other, Each of r1 to r4 is independently an integer of 1 to 3, each of r5 to r9 is independently an integer of 1 to 5, and when each of r1 to r9 is 2 or more, the substituents in the parentheses are the same or different.

[0070] In one embodiment of the present application, Z of the above-mentioned chemical formula A-1 1 ~Z 3 are the same or different and each independently represents N or CH; Z 1 ~Z 3 At least one of the above may be N.

[0071] In one embodiment of the present application, the Z 1 is N and Z 2 and Z 3 is CH.

[0072] In one embodiment of the present application, the Z 2 is N and Z 1 and Z 3 is CH.

[0073] In one embodiment of the present application, the Z 3 is N and Z 1 and Z 2 is CH.

[0074] In one embodiment of the present application, the Z 1 is CH and Z 2 and Z 3 is N.

[0075] In one embodiment of the present application, the Z 2 is CH and Z 1 and Z 3 is N.

[0076] In one embodiment of the present application, the Z 3 is CH and Z 1 and Z 2 is N.

[0077] In one embodiment of the present application, the Z 1 ~Z 3 is N.

[0078] In one embodiment of the present application, Z of the formula A-2 4 ~Z 6 are the same or different and each independently represents N or CH; Z 4 ~Z 6 At least one of the above may be N.

[0079] In one embodiment of the present application, the Z4 is N and Z 5 and Z 6 is CH.

[0080] In one embodiment of the present application, the Z 5 is N and Z 4 and Z 6 is CH.

[0081] In one embodiment of the present application, the Z 6 is N and Z 4 and Z 5 is CH.

[0082] In one embodiment of the present application, the Z 4 is CH and Z 5 and Z 6 is N.

[0083] In one embodiment of the present application, the Z 5 is CH and Z 4 and Z 6 is N.

[0084] In one embodiment of the present application, the Z 6 is CH and Z 4 and Z 5 is N.

[0085] In one embodiment of the present application, the Z 4 ~Z 6 is N.

[0086] In one embodiment of the present application, Z of the formula A-3 7 and Z 8 are the same or different and each independently represents N or CH; Z 7 and Z 8 At least one of the above may be N.

[0087] In one embodiment of the present application, the Z 7 is N and Z 8 is CH.

[0088] In one embodiment of the present application, the Z 8 is N and Z 7 is CH.

[0089] In one embodiment of the present application, the Z 7 and Z 8 is N.

[0090] In one embodiment of the present application, Z of the formula A-4 9 and Z 10 are the same or different and each independently represents N or CH; Z 9 and Z 10 At least one of them may be N.

[0091] In one embodiment of the present application, the Z 9 is N and Z 10 is CH.

[0092] In one embodiment of the present application, the Z 10 is N and Z 9 is CH.

[0093] In one embodiment of the present application, the Z 9 and Z 10 is N.

[0094] In one embodiment of the present application, Z of the formula A-5 11 and Z 12 are the same or different and each independently represents N or CH; Z 11 and Z 12 At least one of them may be N.

[0095] In one embodiment of the present application, the Z 11 is N and Z 12 is CH.

[0096] In one embodiment of the present application, the Z 12 is N and Z 11is CH.

[0097] In one embodiment of the present application, the Z 11 and Z 12 is N.

[0098] In one embodiment of the present application, Z of the formula A-6 13 and Z 14 are the same or different and each independently represents N or CH; Z 13 and Z 14 At least one of the above may be N.

[0099] In one embodiment of the present application, the Z 13 is N and Z 14 is CH.

[0100] In one embodiment of the present application, the Z 14 is N and Z 13 is CH.

[0101] In one embodiment of the present application, the Z 13 and Z 14 is N.

[0102] In one embodiment of the present application, Z of the formula A-7 15 and Z 16 are the same or different and each independently represents N or CH; Z 15 and Z 16 At least one of the above may be N.

[0103] In one embodiment of the present application, the Z 15 is N and Z 16 is CH.

[0104] In one embodiment of the present application, the Z 16 is N and Z 15 is CH.

[0105] In one embodiment of the present application, the Z 15and Z 16 is N.

[0106] In one embodiment of the present application, L of the above chemical formulae A-1 to A-7 1 ~L 9 may be 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.

[0107] In one embodiment of the present application, the L 1 ~L 9 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.

[0108] In one embodiment of the present application, the L 1 ~L 9 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.

[0109] In one embodiment of the present application, the L 1 ~L 9 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.

[0110] In one embodiment of the present application, the L 1 ~L 9 may be the same or different and each independently be a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted naphthalene group.

[0111] In one embodiment of the present application, the L 1 ~L 9 may be the same or different and each independently be a direct bond; a phenylene group; or a naphthalene group.

[0112] In another embodiment, the L 1 is a direct bond.

[0113] In yet another embodiment, the L 1 is a phenylene group.

[0114] In yet another embodiment, the L 1 is a naphthylene group.

[0115] In another embodiment, the L 2 is a direct bond.

[0116] In yet another embodiment, the L 2 is a phenylene group.

[0117] In yet another embodiment, the L 2 is a naphthylene group.

[0118] In another embodiment, the L 3 is a direct bond.

[0119] In yet another embodiment, the L 3 is a phenylene group.

[0120] In yet another embodiment, the L 3 is a naphthylene group.

[0121] In another embodiment, the L 4 is a direct bond.

[0122] In yet another embodiment, the L 4 is a phenylene group.

[0123] In yet another embodiment, the L 4 is a naphthylene group.

[0124] In another embodiment, the L5 is a direct bond.

[0125] In yet another embodiment, the L 5 is a phenylene group.

[0126] In yet another embodiment, the L 5 is a naphthylene group.

[0127] In another embodiment, the L 6 is a direct bond.

[0128] In yet another embodiment, the L 6 is a phenylene group.

[0129] In yet another embodiment, the L 6 is a naphthylene group.

[0130] In another embodiment, the L 7 is a direct bond.

[0131] In yet another embodiment, the L 7 is a phenylene group.

[0132] In yet another embodiment, the L 7 is a naphthylene group.

[0133] In another embodiment, the L 8 is a direct bond.

[0134] In yet another embodiment, the L 8 is a phenylene group.

[0135] In yet another embodiment, the L 8 is a naphthylene group.

[0136] In another embodiment, the L 9 is a direct bond.

[0137] In yet another embodiment, the L 9 is a phenylene group.

[0138] In yet another embodiment, the L 9 is a naphthylene group.

[0139] In one embodiment of the present application, X in the chemical formulae A-5 to A-7 1 ~X 3 are the same or different and may each independently be O; or S.

[0140] In one embodiment of the present application, the X 1 may be O; or S.

[0141] In one embodiment of the present application, the X 1 is O.

[0142] In one embodiment of the present application, the X 1 is S.

[0143] In one embodiment of the present application, the X 2 may be O; or S.

[0144] In one embodiment of the present application, the X 2 is O.

[0145] In one embodiment of the present application, the X 2 is S.

[0146] In one embodiment of the present application, the X 3 may be O; or S.

[0147] In one embodiment of the present application, the X 3 is O.

[0148] In one embodiment of the present application, the X 3 is S.

[0149] In one embodiment of the present application, q1 to q9 in the chemical formulae A-1 to A-7 are each independently an integer of 0 to 2, and when q1 to q9 are each 2, the substituents in the parentheses may be the same or different from each other.

[0150] In one embodiment of the present application, Ar of the above chemical formulae A-1 to A-7 1 ~Ar 9 may be the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0151] In one embodiment of the present application, the Ar 1 ~Ar 9 may be the same or different and each independently be a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0152] In one embodiment of the present application, the Ar 1 ~Ar 9 may 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.

[0153] In one embodiment of the present application, the Ar 1 ~Ar 9 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 terphenyl group; a substituted or unsubstituted triphenyl group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; or a substituted or unsubstituted carbazolyl group.

[0154] In one embodiment of the present application, the Ar 1 ~Ar 9may be the same or different and each independently be a phenyl group; a biphenyl group; a terphenyl group; a triphenyl group; a dibenzofuran group; a dibenzothiophene group; or a carbazolyl group.

[0155] In one embodiment of the present application, r1 to r4 in the chemical formulae A-1 to A-7 are each independently an integer of 1 to 3, r5 to r8 are each independently an integer of 1 to 5, and when r1 to r9 are each 2 or more, the substituents in the parentheses are the same or different from each other.

[0156] In another embodiment, the N-het is unsubstituted or substituted with one or more substituents selected from the group consisting of an aryl group having 6 to 60 carbon atoms and a heteroaryl group having 2 to 60 carbon atoms, and may be a pyridyl group; a pyrimidyl group; a pyridazinyl group; a pyrazolyl group; a triazinyl group; a quinolyl group; an isoquinolyl group; a quinazolinyl group; an isoquinazolinyl group; a quinozolyl group; a naphthyridyl group; a benzothiazole group; or a benzo[4,5]thieno[2,3-d]pyrimidine group.

[0157] In one embodiment of the present application, Ar in the above Chemical Formula 1 may be an amine group substituted or unsubstituted with one or more selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, or a substituted or unsubstituted amine group substituted or unsubstituted with one or more selected from the group consisting of 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.

[0158] In the case of the compound in Formula 1 where Ar is an amine group, the compound has stronger donor properties. Therefore, when the compound is used in an organic layer of an organic light emitting device, it is more effective in hole injection, thereby eliminating the hole trapping phenomenon of the dopant, and thus the efficiency of the organic light emitting device can be further improved.

[0159] In addition, when the compound in Formula 1 where Ar is an amine group has lower HOMO and LUMO levels, when the compound in Formula 1 where Ar is an aryl group or a heteroaryl group is used in an organic layer of an organic light-emitting device, the compound has an energy level difference that is favorable for exciplex formation, thereby further improving the efficiency and lifespan of the organic light-emitting device.

[0160] In one embodiment of the present application, Ar may be a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; or a group represented by the following chemical formula B. [ka]

[0161] In the above chemical formula B, 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 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, m and n are each 0 or 1; [ka] means the position at which it bonds to L in Chemical Formula 1.

[0162] In one embodiment of the present application, the chemical formula B may be represented by any one of the following chemical formulas B-1 to B-5. [ka] [ka] [ka] [ka] [ka]

[0163] In the above chemical formulas B-1 to B-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 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 NRc, wherein Rc is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, c and d are each 0 or 1; e, g, j, and k each represent an integer of 0 to 4, f, h, and i each represent an integer of 0 to 6, and when e to k each represent 2 or more, the substituents in the parentheses are the same or different from each other, [ka] means the position at which it bonds to L in Chemical Formula 1.

[0164] In one embodiment of the present application, L of formula B-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.

[0165] In one embodiment of the present application, L of formula B-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.

[0166] 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.

[0167] 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 substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; or a substituted or unsubstituted naphthalene group.

[0168] 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 phenylene group; a biphenylene group; or a naphthalene group.

[0169] In one embodiment of the present application, the L 13 is a direct bond.

[0170] In one embodiment of the present application, the L 13 is a phenylene group.

[0171] In one embodiment of the present application, the L 13 is a biphenylene group.

[0172] In one embodiment of the present application, the L 13 is a naphthylene group.

[0173] In one embodiment of the present application, the L 14 is a direct bond.

[0174] In one embodiment of the present application, the L 14 is a phenylene group.

[0175] In one embodiment of the present application, the L 14 is a biphenylene group.

[0176] In one embodiment of the present application, the L 14 is a naphthylene group.

[0177] 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 aryl group having 6 to 40 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.

[0178] 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 aryl group having 6 to 40 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.

[0179] 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.

[0180] 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.

[0181] 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 a methyl group; a substituted or unsubstituted dibenzothiophene group; or a substituted or unsubstituted dibenzofuran group.

[0182] In one embodiment of the present application, the Ar 13 and Ar 14may 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.

[0183] In one embodiment of the present application, c and d in the above chemical formula B-1 may be 0 or 1, respectively.

[0184] 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.

[0185] In one embodiment of the present application, the R 20 ~R 26 may each independently be hydrogen; deuterium; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0186] 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.

[0187] In one embodiment of the present application, the R 20 ~R 26 may each independently be a hydrogen atom or a phenyl group.

[0188] In one embodiment of the present application, the R 20 may be hydrogen; or a phenyl group.

[0189] In one embodiment of the present application, X in the formula B-5 11represents O; S; or NRc, and the Rc may be a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0190] In one embodiment of the present application, the X 11 is O; S; or NRc, where Rc may be a phenyl group.

[0191] In one embodiment of the present application, the X 11 is O.

[0192] In one embodiment of the present application, the X 11 is S.

[0193] In one embodiment of the present application, the X 11 is NRc, wherein Rc is a phenyl group.

[0194] In one embodiment of the present application, X in the above formula 1 may be O; or S.

[0195] In one embodiment of the present application, said X is O.

[0196] In one embodiment of the present application, said X is S.

[0197] In one embodiment of the present application, a in the above Chemical Formula 1 is an integer of 0 to 3, and when a is 2 or more, the substituents in the parentheses are the same or different from each other.

[0198] In one embodiment of the present application, a is 3.

[0199] In one embodiment of the present application, a is 2.

[0200] In one embodiment of the present application, a is 1.

[0201] In one embodiment of the present application, a is 0.

[0202] In one embodiment of the present application, b in the above Chemical Formula 1 is an integer of 0 to 4, and when b is 2 or more, the substituents in the parentheses are the same or different from each other.

[0203] In one embodiment of the present application, said b is 4.

[0204] In one embodiment of the present application, b is 3.

[0205] In one embodiment of the present application, said b is 2.

[0206] In one embodiment of the present application, said b is 1.

[0207] In one embodiment of the present application, b is 0.

[0208] In one embodiment of the present application, R p may be hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroaryl group having 6 to 40 carbon atoms.

[0209] In one embodiment of the present application, R p is hydrogen.

[0210] In one embodiment of the present application, p in the above Chemical Formula 1 is an integer of 0 to 6, and when p is 2, the substituents in the parentheses are the same or different from each other.

[0211] In one embodiment of the present application, said p is 6.

[0212] In one embodiment of the present application, said p is 5.

[0213] In one embodiment of the present application, said p is 4.

[0214] In one embodiment of the present application, said p is 3.

[0215] In one embodiment of the present application, said p is 2.

[0216] In one embodiment of the present application, said p is 1.

[0217] In one embodiment of the present application, said p is 0.

[0218] In one embodiment of the present application, the heterocyclic compound represented by Chemical Formula 1 is provided, which is represented by any one of the following compounds: [ka] TIFF0007616693000026.tif218161 TIFF0007616693000027.tif227161 TIFF0007616693000028.tif205161 TIFF0007616693000029.tif224161 TIFF0007616693000030.tif223161 TIFF0007616693000031.tif206161 TIFF0007616693000032.tif211161 TIFF0007616693000033.tif224161 TIFF0007616693000034.tif218161 TIFF0007616693000035.tif215161 TIFF0007616693000036.tif215161 TIFF0007616693000037.tif221161 TIFF0007616693000038.tif222161 TIFF0007616693000039.tif209161 TIFF0007616693000040.tif219161 TIFF0007616693000041.tif223161 TIFF0007616693000042.tif216161TIFF0007616693000043.tif44161

[0219] In addition, it is possible to synthesize compounds having the inherent properties of the introduced substituents by introducing various substituents into the structure of Chemical Formula 1. For example, it is possible to synthesize materials that satisfy the requirements 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.

[0220] In addition, by introducing various substituents into the structure of Chemical Formula 1, the energy band gap can be finely adjusted, while improving the characteristics at the interface between organic materials, thereby diversifying the uses of the material.

[0221] 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 the device with driving stability.

[0222] The heterocyclic compound according to one embodiment of the present application can be prepared by a multi-step chemical reaction. Some intermediate compounds are prepared first, and the compound of Chemical Formula 1 can be prepared from the intermediate compounds. More specifically, the heterocyclic compound according to one embodiment of the present application can be prepared according to the preparation examples described below.

[0223] Another embodiment of the present application provides an organic light-emitting device including a heterocyclic compound represented by Chemical Formula 1. The "organic light-emitting device" may be expressed by terms such as "organic light-emitting diode," "OLED (Organic Light Emitting Diodes)," "OLED device," "organic electroluminescent device," etc.

[0224] 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 comprises a heterocyclic compound represented by Chemical Formula 1.

[0225] In one embodiment of the present application, the first electrode may be an anode and the second electrode may be a cathode.

[0226] In another embodiment of the present application, the first electrode may be a cathode and the second electrode may be an anode.

[0227] 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 Chemical Formula 1 may be used as a material of the blue organic light-emitting device.

[0228] In another embodiment of the present application, the organic light emitting device may be a green organic light emitting device, and the heterocyclic compound of Chemical Formula 1 may be used as a material of the green organic light emitting device.

[0229] In a further embodiment of the present application, the organic light-emitting device may be a red organic light-emitting device, and the heterocyclic compound according to Chemical Formula 1 may be used as a material of the red organic light-emitting device.

[0230] The specific details regarding the heterocyclic compound represented by Chemical Formula 1 are the same as those described above.

[0231] The organic light-emitting device of the present application may 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.

[0232] In the manufacture of 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.

[0233] The organic layer of the organic light-emitting device of the present application may have a single-layer structure, or may have a multi-layer structure in which two or more organic layers are laminated. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a hole auxiliary 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.

[0234] In the organic light emitting device of the present application, the organic layer may include a light emitting layer, and the light emitting layer may include the heterocyclic compound. When the heterocyclic compound is used in the light emitting layer, a strong charge transfer is possible by spatially separating a HOMO (highest occupied molecular orbital) and a LUMO (lowest ighest unoccupied molecular orbital), so that the driving efficiency and life of the organic light emitting device can be excellent. The driving, efficiency and life of the organic light emitting device can be excellent.

[0235] 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, a hole-auxiliary layer, and a hole-blocking layer.

[0236] 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 any structure of an organic light-emitting device known in the art may be applied to the present application.

[0237] 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.

[0238] 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 emission layer 303, a hole blocking layer 304, an electron transport layer 305, and an electron injection layer 306. However, such a laminated structure does not limit the scope of the present application, and the remaining layers except for the emission layer may be omitted as necessary, and other necessary functional layers may be further added.

[0239] The organic layer containing the compound represented by Chemical Formula 1 may further contain other materials, if necessary.

[0240] In an organic light-emitting device according to an embodiment of the present application, materials other than the compound of Chemical Formula 1 are exemplified below. However, these are merely examples and are not intended to limit the scope of the present application, and may be replaced with materials known in the art.

[0241] 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 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); ZnO:Al or SnO 2 Examples of the conductive material include, but are not limited to: a combination of a metal and an oxide, such as Sb; and conductive polymers, such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

[0242] 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 metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; LiF / Al, or LiO 2 Examples of the material include, but are not limited to, a multi-layer structure such as / Al.

[0243] The hole injection material may be a known hole injection material, for example, a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Pat. No. 4,356,429, or a starburst type amine derivative described in the literature [Advanced Material, 6, p. 677 (1994)], for example, tris(4-carbazoyl-9-ylphenyl)amine (TCTA), 4,4',4''-tri[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB), a soluble conductive polymer, polyaniline / dodecylbenzenesulfonic acid (Polyaniline / Dodecylbenzenesulfonic acid), etc. Alternatively, poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate), polyaniline / Camphor sulfonic acid, or polyaniline / Poly(4-styrenesulfonate) may be used.

[0244] As the hole transport material, a pyrazoline derivative, an arylamine derivative, a stilbene derivative, a triphenyldiamine derivative, or the like may be used, and a low molecular weight or high molecular weight material may also be used.

[0245] As the electron transport material, oxadiazole derivatives, anthraquinodimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinodimethane and its derivatives, fluorenone derivatives, diphenyldicyanoethylene and its derivatives, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and its derivatives, etc. may be used, and not only low molecular weight substances but also polymeric substances may be used.

[0246] As the electron injection material, for example, LiF is typically used in the industry, but the present application is not limited thereto.

[0247] The light-emitting material may be a red, green or blue light-emitting material, and if necessary, two or more light-emitting materials may be mixed and used. In this case, two or more light-emitting materials may be deposited as individual supply sources, or may be premixed and deposited as one supply source. The light-emitting material may be a fluorescent material or a phosphorescent material. The light-emitting material may be a material that emits light by combining holes and electrons injected from the anode and cathode, respectively, or a material in which both the host material and the dopant material are involved in light emission may be used.

[0248] When the hosts of the light-emitting materials are mixed, the hosts may be of the same type or different types. For example, two or more of n-type host materials or p-type host materials may be selected and used as the host material of the light-emitting layer.

[0249] In the organic light-emitting device of the present application, the organic layer may include a light-emitting layer, and the light-emitting layer may include the heterocyclic compound as a host substance of a light-emitting material.

[0250] In the organic light-emitting device of the present application, the light-emitting layer may contain two or more host substances, and at least one of the host substances may contain the heterocyclic compound as a host substance of a light-emitting material.

[0251] In the organic light-emitting device of the present application, the light-emitting layer may be a pre-mixed mixture of 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.

[0252] The term "pre-mixed" means that the light-emitting layer is prepared by mixing two or more host materials in a single source before depositing the materials on the organic layer.

[0253] In the organic light-emitting device of the present application, the light-emitting layer may 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 may include the heterocyclic compound as a host material of a light-emitting material. In this case, the organic light-emitting device may have excellent driving, efficiency, and life.

[0254] In the organic light-emitting device of the present application, the light-emitting layer may contain two or more kinds of the heterocyclic compounds represented by Chemical Formula 1.

[0255] In the organic light-emitting device of the present application, the light-emitting layer may contain two kinds of the heterocyclic compounds represented by Chemical Formula 1.

[0256] When two or more heterocyclic compounds represented by Formula 1 are used in the light-emitting layer, exciplexes are formed, thereby improving device performance.

[0257] In one embodiment of the present application, two or more of the heterocyclic compounds represented by Chemical Formula 1 may be used simultaneously as the host material.

[0258] In one embodiment of the present application, there is provided a composition for an organic layer of an organic light-emitting device, comprising two or more of the heterocyclic compounds represented by Chemical Formula 1.

[0259] In one embodiment of the present application, there is provided a composition for an organic layer of an organic light-emitting device, comprising two of the heterocyclic compounds represented by Chemical Formula 1.

[0260] The weight ratio of the two heterocyclic compounds represented by Chemical Formula 1 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.

[0261] The organic light emitting device according to one embodiment of the present application may be front-emitting, back-emitting or dual-sided emitting, depending on the materials used.

[0262] The heterocyclic compound according to one embodiment of the present application may also function in organic electronic devices such as organic solar cells, organic photoreceptors, and organic transistors based on a similar principle to that applied to organic light emitting devices. EXAMPLES

[0263] The present specification will be described in more detail below with reference to examples. However, these are merely for illustrating the present application and are not intended to limit the scope of the present application.

[0264] <Production Example> [Production Example 1] Production of Compound 1 [ka]

[0265] 1) Preparation of Compound 1-1 In a one neck round bottom flask (One neck rbf), a mixture of 1-bromo-4-chloro-3-fluoro-2-iodobenzene (50 g, 150 mmol), (3-methoxynaphthalen-2-yl)boronic acid (30 g, 150 mmol), tetrakis(triphenylphosphine)palladium(0) (17 g, 15 mmol), potassium carbonate (62 g, 450 mmol), and toluene / ethanol / water (500 ml / 100 ml / 100 ml) was refluxed and stirred at 110° C., then extracted with dichloromethane and diluted with MgSO 4 After drying at 40° C., compound 1-1 was obtained by silica gel column chromatography purification (48 g, 88%).

[0266] 2) Preparation of Compound 1-2 In a one-neck round-bottom flask, a mixture of compound 1-1 (48 g, 132 mmol) and dichloromethane (1000 ml) was cooled to 0° C. 3 (26 mL, 270 mmol) was added dropwise, and the mixture was heated to room temperature and stirred for 2 hours. The reaction was then terminated with distilled water, extracted with dichloromethane, and diluted with MgSO 4 The mixture was dried at rt and purified by silica gel column chromatography to obtain compound 1-2 (37 g, 80%).

[0267] 3) Preparation of Compound 1-3 In a one-neck round-bottom flask, compound 1-2 (37 g, 106 mmol), Cs 2 CO 3 A mixture of (172 g, 530 mmol) and dimethylacetamide (400 ml) was stirred at 120° C. Then, it was cooled to room temperature and filtered, and the solvent of the filtrate was removed, and the compound 1-3 (32 g, 88%) was obtained by purification using silica gel column chromatography.

[0268] 4) Preparation of Compound 1-4 In a one neck round bottom flask, compound 1-3 (10 g, 30 mmol), 7H-dibenzo[c,g]carbazole (8 g, 30 mmol), and Cs 2 CO 3 A mixture of (48 g, 150 mmol) and dimethylacetamide (100 ml) was refluxed and stirred at 170° C. for 12 h. After cooling to room temperature, the mixture was filtered, and the solvent was removed from the filtrate. Compound 1-4 (11.3 g, 73%) was obtained by purification using silica gel column chromatography.

[0269] 5) Preparation of Compound 1-5 In a one neck round bottom flask (one neck rbf), compound 1-4 (11.8 g, 22 mmol), bis(pinacolato)diboron (12 g, 44 mmol), XPhos (2.0 g, 4.4 mmol), potassium acetate (6.4 g, 66 mmol), Pd(dba) 2 A mixture of (1.2 g, 2.2 mmol) and 1,4-dioxane (100 ml) was refluxed and stirred at 140° C. Then, it was extracted with dichloromethane and concentrated, and the resulting solid was purified by recrystallization using dichloromethane / MeOH to obtain compound 1-5 (12.8 g, 96%).

[0270] 6) Preparation of Compound 1 In a one neck round bottom flask (One neck rbf), a mixture of compound 1-5 (12.8g, 21.1mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (5.8g, 22mmol), tetrakis(triphenylphosphine)palladium(0) (2.4g, 2.11mmol), potassium carbonate (8.7g, 63.3mmol), and 1,4-dioxane / water (120ml / 24ml) was refluxed and stirred at 120°C for 3 hours. The solid precipitated during the reaction was filtered in a hot state and purified with 1,4-dioxane, distilled water, and MeOH to obtain compound 1 (10.5g, 70%).

[0271] The target compound in Table 1 was synthesized in the same manner as in the production of Compound 1 in Production Example 1, except that in Production Example 1, A in Table 1 was used instead of 7H-dibenzo[c,g]carbazole and B in Table 1 was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0272] [Table 1]

[0273] In the production of compound 1-3 in Production Example 1, the positions of -Br and -Cl in compound 1-3 vary depending on -Br and -Cl in 1-bromo-4-chloro-3-fluoro-2-iodobenzene, and the intermediates that can be synthesized are as follows. [ka]

[0274] In the same manner as in the preparation of compound 1, except that in Preparation Example 1, instead of compound 1-3, one of intermediates C-0, D-0, E-0, F-0 and G-0 was used as shown in Table 2 below, and A and B in Table 2 below were used, the target compound in Table 2 below was synthesized.

[0275] [Table 2]

[0276] [Production Example 2] Production of Compound 9 [ka]

[0277] 1) Preparation of Compound 9-1 In a one neck round bottom flask (One neck rbf), a mixture of compound 1-3 (30 g, 90 mmol), N-phenyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)dibenzo[b,d]thiophene-2-amine (42 g, 90 mmol), tetrakis(triphenylphosphine)palladium(0) (10 g, 9 mmol), potassium carbonate (37 g, 270 mmol), and toluene / ethanol / water (300 ml / 60 ml / 60 ml) was refluxed and stirred at 110° C. Then, the mixture was extracted with dichloromethane and diluted with MgSO 4 After drying at 40° C., compound 9-1 was obtained using silica gel column chromatography purification (66 g, 92%).

[0278] 2) Preparation of Compound 9-2 In a one neck round bottom flask (one neck rbf), compound 9-1 (10 g, 16 mmol), bis(pinacolato)diboron (8 g, 32 mmol), XPhos (1.5 g, 3.2 mmol), potassium acetate (4.7 g, 48 mmol), and Pd(dba) were added. 2 A mixture of (0.9 g, 1.6 mmol) and 1,4-dioxane (100 ml) was refluxed and stirred at 140° C. Then, it was extracted with dichloromethane and concentrated. The solid thus produced was purified by recrystallization using dichloromethane / MeOH to obtain compound 9-2 (8.8 g, 88%).

[0279] 3) Preparation of Compound 9 In a one neck round bottom flask (One neck rbf), a mixture of compound 9-2 (8.8g, 14mmol), 6-chloro-3,5-diphenyl-1,2,4-triazine (3.7g, 14mmol), tetrakis(triphenylphosphine)palladium(0) (1.6g, 1.4mmol), potassium carbonate (5.7g, 42mmol), and 1,4-dioxane / water (100ml / 20ml) was refluxed and stirred at 120°C for 3 hours. The solid precipitated during the reaction was then filtered in a hot state and purified with 1,4-dioxane, distilled water, and MeOH to obtain compound 9 (9.0g, 81%).

[0280] The target compound in Table 3 was synthesized in the same manner as in the production of Compound 9 in Production Example 2, except that in Production Example 2, A in Table 3 was used instead of N-phenyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)dibenzo[b,d]thiophene-2-amine and B in Table 3 were used instead of 6-chloro-3,5-diphenyl-1,2,4-triazine.

[0281] [Table 3]

[0282] Similarly, in the above Production Example 2, the following intermediate may be used instead of compound 1-3. [ka]

[0283] In the same manner as in the preparation of compound 9, the target compound in Table 4 was synthesized, except that in Preparation Example 2, one of C-0, D-0, E-0, F-0 and G-0 was used instead of compound 1-3 as shown in Table 2, and A and B in Table 4 were used.

[0284] [Table 4] TIFF0007616693000052.tif205165 TIFF0007616693000053.tif199165

[0285] [Production Example 3] Production of Compound 77 [ka]

[0286] 1) Preparation of Compound 77-1 Compound 77-1 was prepared in the same manner as in the preparation of compound 1-3, except that in Preparation Example 1, (1-methoxynaphthalen-2-yl)boronic acid was used instead of (3-methoxynaphthalen-2-yl)boronic acid.

[0287] 2) Preparation of Compound 77 Compound 77 (8.3 g, 72%) was prepared in the same manner as in the preparation of Compound 1, except that Compound 77-1 was used instead of Compound 1-3 in Preparation Example 1.

[0288] The target compound in Table 5 was synthesized in the same manner as in the production of Compound 77 in Production Example 3, except that in Production Example 3, A in Table 5 was used instead of 7H-dibenzo[c,g]carbazole and B in Table 5 was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0289] [Table 5]

[0290] In the above Production Example 3, the positions of -Br and -Cl in Compound 1-3 vary depending on -Br and -Cl in 1-bromo-4-chloro-3-fluoro-2-iodobenzene, and the intermediates that can be synthesized thereby are as follows. [ka]

[0291] In the same manner as in the preparation of compound 77, except that in Preparation Example 3, instead of compound 77-1, one of the intermediates C-1, D-1, E-1, F-1 and G-1 was used as shown in Table 6 below, and A and B in Table 6 below were used, the target compound in Table 6 below was synthesized.

[0292] [Table 6]

[0293] [Production Example 4] Production of Compound 90 [ka]

[0294] 1) Preparation of Compound 90-1 Compound 90-1 was obtained by using compound 77-1 of Production Example 3 instead of compound 9-1 of Production Example 2 and using 9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole instead of N-phenyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)dibenzo[b,d]thiophene-2-amine.

[0295] 2) Preparation of Compound 90 Compound 90 (13.2 g, 72%) was obtained in the same manner as in Preparation Example 2, except that compound 90-1 was used instead of compound 9-1.

[0296] The following target compound was synthesized in the same manner as in the production of compound 90 in Production Example 4, except that A and B in Table 7 below were used in Production Example 4.

[0297] [Table 7]

[0298] Similarly, in the above Production Example 4, the following intermediate may be used instead of compound 77-1. [ka]

[0299] The target compound in Table 8 was synthesized in the same manner as in the preparation of compound 90, except that in Preparation Example 4, one of C-1, D-1, E-1, F-1 and G-1 as shown in Table 8 below was used instead of compound 77-1, and A and B in Table 8 below were used.

[0300] [Table 8] TIFF0007616693000062.tif124165

[0301] [Production Example 5] Production of Compound 157 [ka]

[0302] 1) Preparation of Compound 157-1 Compound 157-1 was prepared in the same manner as in preparation of compound 1-3, except that (2-methoxynaphthalen-1-yl)boronic acid was used instead of (3-methoxynaphthalen-2-yl)boronic acid in Preparation Example 1.

[0303] 2) Preparation of Compound 157 Compound 157 (9.5 g, 84%) was prepared in the same manner as in the preparation of Compound 1, except that Compound 157-1 was used instead of Compound 1-3 in Preparation Example 1.

[0304] The target compound in Table 9 was synthesized in the same manner as in the production of compound 157 in Production Example 5, except that in Production Example 5, A in Table 9 was used instead of 7H-dibenzo[c,g]carbazole and B in Table 9 was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0305] [Table 9]

[0306] In the above Production Example 5, the positions of -Br and -Cl in compound 157-1 vary depending on -Br and -Cl in 1-bromo-4-chloro-3-fluoro-2-iodobenzene, and the intermediates that can be synthesized thereby are as follows. [ka]

[0307] In the same manner as in the preparation of compound 157, except that in Preparation Example 5, instead of compound 157-1, one of C-2, D-2, E-2, F-2 and G-2 as shown in Table 10 below was used, and A and B in Table 10 below were used, the target compound in Table 10 below was synthesized.

[0308] [Table 10] TIFF0007616693000067.tif85165

[0309] [Production Example 6] Production of Compound 165 [ka]

[0310] 1) Preparation of Compound 165 Compound 165 (5.8 g, 68%) was obtained in the same manner as in Preparation Example 4, except that compound 157-1 was used instead of compound 77-1.

[0311] The target compound in Table 11 below was synthesized in the same manner as in the production of compound 165 in Production Example 6 above, except that A and B in Table 11 below were used in Production Example 6 above.

[0312] [Table 11]

[0313] Similarly, in the above Production Example 6, the following intermediate may be used instead of compound 157-1. [ka]

[0314] [Table 12] TIFF0007616693000072.tif86165

[0315] Compounds were produced in the same manner as in the above-mentioned production examples, and the results of synthesis are shown in Tables 13 and 14 below. 1 H NMR (CDCl 3 , 300 MHz), and Table 14 below shows the measured values ​​by FD-MS (Field desorption mass spectrometry).

[0316] [Table 13] TIFF0007616693000074.tif230165 TIFF0007616693000075.tif230165 TIFF0007616693000076.tif133165

[0317] [Table 14] TIFF0007616693000078.tif231165 TIFF0007616693000079.tif231165 TIFF0007616693000080.tif231165 TIFF0007616693000081.tif125165

[0318] <Experimental Example 1> - Fabrication of organic light-emitting device 1) Preparation of organic light-emitting device (Red single host) A glass substrate coated with a thin indium tin oxide (ITO) film to a thickness of 1,500 Å was ultrasonically cleaned with distilled water. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UVO for 5 minutes using UV in a UV cleaner. The substrate was then transferred to a plasma cleaner (PT) and plasma treated in a vacuum state to determine the work function of the ITO and remove residual film, and then transferred to a thermal evaporation device for organic deposition.

[0319] On the ITO transparent electrode (anode), a hole injection layer made of 2-TNATA (4,4',4''-tris[2-naphthyl(phenyl)amino]triphenylamine) and a hole transport layer made of NPB (N,N'-di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine) were formed as a common layer.

[0320] An emitting layer was then thermally vacuum deposited thereon as follows: The emitting layer contained a compound shown in Table 15 below as a red host, (piq) as a red phosphorescent dopant, 2 (Ir)(acac) and (piq) to the host 2 (Ir)(acac) was doped at 3 wt% and evaporated to a thickness of 500 Å. Then, BCP was evaporated to a thickness of 60 Å as a hole blocking layer, and Alq was evaporated on top of it as an electron transport layer. 3 Then, BCP was deposited to 60 Å as a hole blocking layer, and Alq was deposited on it as an electron transport layer. 3 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 manufacturing an organic light emitting device (Examples 1 to 18 and Comparative Examples 1 to 6).

[0321] On the other hand, all the organic compounds required for the production of OLED elements are about 10 -6 ~10-8 The resulting material was purified by vacuum sublimation under torr and used to fabricate OLEDs.

[0322] 2) Driving voltage and luminous efficiency of organic light-emitting devices The electroluminescence (EL) characteristics of the organic light-emitting devices of Examples 1 to 18 and Comparative Examples 1 to 6 prepared as described above were measured using a McScience M7000. Using the measurement results, a reference luminance of 6,000 cd / m was measured using a McScience M6000 lifetime measurement device. 2 T when 90 The above T 90 means the lifetime (unit: h), which is the time it takes for the brightness to reach 90% of the initial brightness.

[0323] The characteristics of the organic light-emitting device of the present invention are as shown in Table 15 below.

[0324] [Table 15]

[0325] The comparative compounds A to F in Table 15 are as follows. [ka]

[0326] As can be seen from the results of Table 15, the organic light emitting device using the heterocyclic compound of the present invention had a lower driving voltage and significantly improved luminous efficiency and life span compared to Comparative Examples 1 to 6. This is believed to be because the compound of the present invention has high thermal stability, heteroaryl groups are linked without a linker, and have an appropriate molecular weight and band gap. That is, when the heterocyclic compound of the present invention is used in the light emitting layer, an appropriate band gap is formed in the light emitting layer, which can prevent the loss of electrons and holes and help form an effective recombination zone of electrons and holes.

[0327] In particular, it has been confirmed that the compound having an arylamine group has a relatively short lifetime and high efficiency among the compounds of the present invention, and the strong HT characteristics of the arylamine group eliminates hole traps generated in the dopant.

[0328] <Experimental Example 2>-Preparation of organic light-emitting device (Red N+P mixed host) 1) Preparation of organic light-emitting device (Red N+P mixed host) A glass substrate coated with a thin indium tin oxide (ITO) film to a thickness of 1,500 Å was ultrasonically cleaned with distilled water. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UVO for 5 minutes using UV in a UV cleaner. The substrate was then transferred to a plasma cleaner (PT) and plasma treated in a vacuum state to determine the work function of the ITO and remove residual film, and then transferred to a thermal evaporation device for organic deposition.

[0329] On the ITO transparent electrode (anode), a hole injection layer made of 2-TNATA (4,4',4''-tris[2-naphthyl(phenyl)amino]triphenylamine) and a hole transport layer made of NPB (N,N'-di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine) were formed as a common layer.

[0330] The light-emitting layer was then deposited thereon by thermal vacuum deposition as follows: The light-emitting layer was formed by depositing a mixture of an arylamine compound and a unipolar compound or a mixture of an arylamine compound and a bipolar compound as shown in Table 16 below as a red host to a thickness of 400 Å, and the red phosphorescent dopant was (piq) 2 The film was evaporated with 3 wt% doping of (Ir)(acac).

[0331] From the element evaluation results of compound 14 and compound 295 (Examples 19 to 23), it was confirmed that a ratio of 1:1 showed the best performance, and the deposition ratio of the arylamine and unipolar compound was then fixed at 1:1, and from the element evaluation results of compound 13 and compound 22 (Examples 34 to 38), the deposition ratio of the arylamine and bipolar compound was fixed at 1:2.

[0332] Then, BCP was evaporated to 60 Å as a hole blocking layer, and Alq was evaporated on it as an electron transport layer. 3 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 manufacturing an organic light emitting device (Examples 19 to 41).

[0333] In addition, as shown in Table 17 below, the organic light-emitting devices of Examples 42 to 65 were manufactured in the same manner as in the manufacture of the organic light-emitting devices of Examples 19 to 41, except that the compound of the present invention and compounds G to P were used.

[0334] Specifically, a deposition ratio test of compound G and compound 243 confirmed that a 1:1 ratio showed the best performance, and the subsequent evaluation of the device was performed with the ratio fixed.

[0335] On the other hand, all the organic compounds required for the production of OLED elements are about 10 -6 ~10 -8 The resulting material was purified by vacuum sublimation under torr and used to fabricate OLEDs.

[0336] 2) Driving voltage and luminous efficiency of organic light-emitting devices The electroluminescence (EL) characteristics of the organic light-emitting devices of Examples 19 to 65 prepared as described above were measured using a Mac Science M7000. Using the measurement results, a reference luminance of 6,000 cd / m was measured using a Mac Science M6000 lifetime measurement device. 2 T when90 The above T 90 means the lifetime (unit: h), which is the time it takes for the brightness to reach 90% of the initial brightness.

[0337] The characteristics of the organic light-emitting device of the present invention are shown in Tables 16 and 17 below.

[0338] [Table 16] TIFF0007616693000085.tif173165

[0339] [Table 17] TIFF0007616693000087.tif191165

[0340] Compounds G to P listed in Table 17 are as follows. [ka]

[0341] The compounds G to K are arylamine derivatives different from the compounds of the present invention, and the compounds L to P are compounds corresponding to typical biscarbazole or indolecarbazole derivatives used as P-type hosts.

[0342] As can be seen from the results of Tables 16 and 17, when the light-emitting layer of the organic light-emitting device is vapor-deposited by mixing the compound according to the present application, it shows more excellent efficiency and life effect. This result is considered to be the result of improving the life-span reduction phenomenon that generally occurs when a compound containing an arylamine group is used in the light-emitting layer of the organic light-emitting device.

[0343] That is, when a host having strong HT characteristics and a compound according to the present application are simultaneously included, it is expected that an exciplex phenomenon of an N+P compound will occur. The exciplex phenomenon of an N+P compound refers to a phenomenon in which energy of the magnitude of the HOMO level of the donor (p-host) and the LUMO level of the acceptor (n-host) is released due to electron exchange between two molecules. In this way, when a donor (p-host) with good hole transporting ability and an acceptor (n-host) with good electron transporting ability are used as a host of the light emitting layer, holes are injected into the p-host and electrons are injected into the n-host due to the exciplex phenomenon of the N+P compound, which can reduce the driving voltage and thereby help improve the lifespan. [Explanation of symbols]

[0344] 100 ···Substrate 200...Anode 300...organic layer 301 Hole injection layer 302 Hole transport layer 303 Light-emitting layer 304 Hole blocking layer 305...electron transport layer 306...electron injection layer 400...Cathode

Claims

1. A heterocyclic compound represented by the following chemical formula 1: 【Chemistry 1】 In the above Chemical Formula 1, L is a direct bond; or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; X is O; N-het is represented by the following chemical formula A: Ar is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; a substituted or unsubstituted heteroaryl group containing O or S and having 2 to 60 carbon atoms; or a group represented by any one of the following chemical formulas B-1, B-2, B-4, and B-5, R ｐ is hydrogen; or deuterium, a is an integer from 1 to 3, and when a is 2 or more, the substituents in the parentheses are the same or different; b is an integer from 1 to 4, and when b is 2 or more, the substituents in the brackets are the same or different; p is an integer from 0 to 6, and when p is 2 or more, the substituents within the brackets are the same or different from each other; 【Chemistry 5】 In the above chemical formula A, * indicates the position where Formula 1 and N-het are bonded, Y １ ~Y ５ are the same or different, and each independently represents N or CRa; Y １ ~Y ５ At least two of the groups are N, and when CRa is two or more, each Ra is the same or different, wherein Ra 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; 【Chemistry 15】 【Chemistry 16】 【Chemistry 18】 【Chemistry 19】 In the above chemical formulas B-1, B-2, B-4 and B-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 ２３ ~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 NRc, wherein Rc is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; c and d are each 0 or 1; e, j, and k each represent an integer from 0 to 4, h and i each represent an integer from 0 to 6, and when e to k each represent 2 or more, the substituents in the brackets are the same or different from each other, 【Chemistry 20】 means the position at which the group is bonded to L in Formula 1.

2. The heterocyclic compound according to claim 1, wherein the "substituted or unsubstituted" means that the heterocyclic compound 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 chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-3: 【Chemistry 2】 【Chemistry 3】 【Chemistry 4】 In the above Chemical Formulas 1-1 to 1-3, the definitions of each substituent are the same as those in Chemical Formula 1.

4. The heterocyclic compound according to claim 1, wherein the chemical formula A is represented by any one of the following chemical formulas A-1 to A-7: 【Chemistry 6】 【Chemistry 7】 【Chemistry 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 In the above chemical formulas A-1 to A-7, * indicates the position where Formula 1 and N-het are bonded, Z １ ~Z １６ are the same or different and each independently represents N or CH; Z １ ~Z ３ At least two of the above are N, and Z ４ ~Z ６ At least two of the above are N, and Z ７ and Z ８ is N, and Z ９ and Z １０ is N, and Z １１ and Z １２ is N, and Z １３ and Z １４ is N, and Z １５ and Z １６ is N, L １ ~L ９ 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, Ar １ ~Ar ９ are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, X １ ~X ３ are the same or different and each independently represents O; or S; q1 to q9 each independently represent an integer of 0 to 2, and when each of q1 to q9 is 2, the substituents in the parentheses are the same or different from each other, Each of r1 to r4 is independently an integer of 1 to 3, and each of r5 to r9 is independently an integer of 1 to 5. When each of r1 to q9 is 2 or more, the substituents in the parentheses are the same or different.

5. The heterocyclic compound according to claim 1 , wherein the chemical formula 1 is represented by any one of the following compounds: 【Chemistry 21】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】

6. 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 5.

7. The organic light-emitting element according to claim 6 , wherein the organic layer includes a light-emitting layer, and the light-emitting layer includes the heterocyclic compound.

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

9. The organic light-emitting device according to claim 6, 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, a hole-assisting layer, and a hole-blocking layer.

10. 7. The organic light emitting device according to claim 6, wherein the light emitting layer can be used by pre-mixing two or more host materials, and at least one of the two or more host materials contains the heterocyclic compound as a host material of a light emitting material.

11. A composition for an organic layer of an organic light-emitting device, comprising two or more of the heterocyclic compounds represented by Chemical Formula 1 according to claim 1 .

12. The composition for an organic layer of an organic light emitting device according to claim 11, wherein the weight ratio of the two heterocyclic compounds represented by Chemical Formula 1 in the composition is 1:10 to 10:1.

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