Heterocyclic compound and organic light-emitting device including the same

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. 10-2019-0171467, filed with the Korean Intellectual Property Office on December 20, 2019, the entire contents of which are incorporated herein by reference.

[0002] The present specification relates to a heterocyclic compound and an organic light-emitting device including the same. [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] There is a continuing need to develop materials for organic thin films to improve the performance, lifetime or efficiency of organic light emitting devices. [Prior art documents] [Patent documents]

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

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

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

[0010] [ka] In the above Chemical Formula 1, L1 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; X1 is O; or S; R p is hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; or a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, R1 to R8 are the same or different and each independently 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; Ar1 is an 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; 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 40 carbon atoms and a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms; a is an integer of 0 to 2, and when a is 2, the substituents in the parentheses are the same or different from each other, Each p is an integer of 0 to 4, and when p is 2 or more, the substituents in the parentheses are the same or different.

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

[0012] The heterocyclic compound described herein can be used as a material for an organic layer of an organic light-emitting device, and can act as a hole injection material, a hole transport material, a light-emitting material, an electron transport material, an electron injection material, etc. in the organic light-emitting device.

[0013] Specifically, when the heterocyclic compound represented by Chemical Formula 1 is used in an organic layer of an organic light emitting device, 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]

[0014] [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

[0015] This specification will be explained in more detail below.

[0016] 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.

[0017] 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.

[0018] 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.

[0019] 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.

[0020] In this specification, the halogen may be fluorine, chlorine, bromine or iodine.

[0021] 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.

[0022] 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.

[0023] 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.

[0024] 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.

[0025] 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.

[0026] 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.

[0027] 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.

[0028] 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.

[0029] 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.

[0030] As used herein, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

[0031] 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.

[0032] [ka] In this specification, the heteroaryl group includes S, O, Se, N or Si as a heteroatom, includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted with other substituents. Here, the polycyclic ring means a group in which the heteroaryl group is directly 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.

[0033] In this specification, the amine group may be selected from the group consisting of a monoalkylamine group, a monoarylamine group, a monoheteroarylamine group, -NH2, a dialkylamine group, a diarylamine group, a diheteroarylamine group, an alkylarylamine group, an alkylheteroarylamine group, and an arylheteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, a dibiphenylamine group, an anthracenylamine group, a 9-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.

[0034] 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.

[0035] 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.

[0036] 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.

[0037] 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%.

[0038] 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.

[0039] 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.

[0040] 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.

[0041] 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.

[0042] 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.

[0043] [ka] 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.

[0044] In one embodiment of the present application, there is provided a heterocyclic compound represented by the following Chemical Formula 1:

[0045] [ka] In the above Chemical Formula 1, L1 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; X1 is O; or S; R p is hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; or a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, R1 to R8 are the same or different and each independently 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; Ar1 is an 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; 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 40 carbon atoms and a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms; a is an integer of 0 to 2, and when a is 2, the substituents in the parentheses are the same or different from each other, Each p is an integer of 0 to 4, and when p is 2 or more, the substituents in the parentheses are the same or different.

[0046] The heterocyclic compound represented by Chemical Formula 1 has a steric configuration by fixing a substituent at a specific position, and can spatially separate the HOMO (highest occupied molecular orbital) and the LUMO (lowest ighest unoccupied molecular orbital) to enable strong charge transfer. Therefore, when used as an organic material in an organic light-emitting device, it is expected to increase the efficiency and lifetime of the organic light-emitting device.

[0047] In one embodiment of the present application, L1 in Chemical Formula 1 may be a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group.

[0048] In another embodiment, L1 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.

[0049] In still another embodiment, the L1 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.

[0050] In still another embodiment, the L1 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.

[0051] In yet another embodiment, L1 may be a direct bond; or a substituted or unsubstituted phenylene group.

[0052] In yet another embodiment, L1 may be a direct bond; or a phenylene group.

[0053] In yet another embodiment, L1 is a direct bond.

[0054] In yet another embodiment, L1 is a phenylene group.

[0055] In one embodiment of the present application, a in the above Chemical Formula 1 is an integer of 0 to 2, and when a is 2, the substituents in the parentheses are the same or different from each other.

[0056] In one embodiment of the present application, a is 2.

[0057] In one embodiment of the present application, a is 1.

[0058] In one embodiment of the present application, a is 0.

[0059] In the case where a heterocyclic compound represented by Formula 1 in which L1 is not a direct bond or a is not 0 is used as an organic material in an organic light-emitting device, the efficiency and life span of the organic light-emitting device are superior to those in which L1 is a direct bond or a is 0. This is believed to be because the presence of a substituent in L1 allows for further spatial separation of the HOMO and LUMO, enabling stronger charge transfer.

[0060] In one embodiment of the present application, X1 in the above formula 1 may be O; or S.

[0061] In one embodiment of the present application, X1 is O.

[0062] In one embodiment of the present application, X1 is S.

[0063] 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; or a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms.

[0064] In one embodiment of the present application, R p is hydrogen.

[0065] In one embodiment of the present application, the above-mentioned Chemical Formula 1 may be represented by the following Chemical Formula 1-1.

[0066] [ka] In the above Chemical Formula 1-1, the definitions of each substituent are the same as those in Chemical Formula 1.

[0067] In one embodiment of the present application, R1 to R8 in Chemical Formula 1 are the same or different and are each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, or two or more groups adjacent to each other 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, R1 to R8 are the same or different and each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms, or two or more groups adjacent to each other may be bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 40 carbon atoms, or a substituted or unsubstituted heterocycle having 2 to 40 carbon atoms.

[0069] In one embodiment of the present application, R1 to R8 are the same or different and each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms, or two or more groups adjacent to each other may be bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 20 carbon atoms, or a substituted or unsubstituted heterocycle having 2 to 20 carbon atoms.

[0070] In one embodiment of the present application, R1 to R8 are the same or different and each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 10 carbon atoms, or two or more groups adjacent to each other may be bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 10 carbon atoms, or a substituted or unsubstituted heterocycle having 2 to 10 carbon atoms.

[0071] In one embodiment of the present application, R1 to R8 are the same or different and each independently selected from the group consisting of hydrogen; deuterium; and a substituted or unsubstituted aryl group having 6 to 40 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 40 carbon atoms.

[0072] In one embodiment of the present application, R1 to R8 are the same or different and each independently selected from the group consisting of hydrogen; deuterium; and a substituted or unsubstituted aryl group having 6 to 20 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 20 carbon atoms.

[0073] In one embodiment of the present application, R1 to R8 are the same or different and each independently selected from the group consisting of hydrogen; deuterium; and a substituted or unsubstituted aryl group having 6 to 10 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 10 carbon atoms.

[0074] In one embodiment of the present application, R1 to R8 are the same or different and each independently selected from the group consisting of hydrogen; deuterium; and a substituted or unsubstituted phenyl group, or two or more adjacent groups may be bonded to each other to form a substituted or unsubstituted benzene ring.

[0075] In one embodiment of the present application, R1 and R8 are each independently hydrogen or deuterium, and R2 to R7 are the same or different and each independently 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, and two or more adjacent groups among R2 to R7 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.

[0076] In one embodiment of the present application, R1 and R8 are each independently hydrogen or deuterium, and R2 to R7 are the same or different and each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms, and two or more adjacent groups among R2 to R7 may be bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 40 carbon atoms, or a substituted or unsubstituted heterocycle having 2 to 40 carbon atoms.

[0077] In one embodiment of the present application, R1 and R8 are each independently hydrogen or deuterium, and R2 to R7 are the same or different and each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms, and two or more adjacent groups among R2 to R7 may be bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 20 carbon atoms, or a substituted or unsubstituted heterocycle having 2 to 20 carbon atoms.

[0078] In one embodiment of the present application, R1 and R8 are each independently hydrogen or deuterium, and R2 to R7 are the same or different and each independently selected from the group consisting of hydrogen, deuterium, and a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, and two or more adjacent groups among R2 to R7 may be bonded to each other to form a substituted or unsubstituted aromatic ring having 6 to 60 carbon atoms.

[0079] In one embodiment of the present application, R1 and R8 are each independently hydrogen or deuterium, and R2 to R7 are the same or different and each independently selected from the group consisting of hydrogen, deuterium, and a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, and two or more adjacent groups among R2 to R7 may be bonded to each other to form a substituted or unsubstituted aromatic ring having 6 to 40 carbon atoms.

[0080] In one embodiment of the present application, R1 and R8 are each independently hydrogen or deuterium, and R2 to R7 are the same or different and each independently selected from the group consisting of hydrogen, deuterium, and a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and two or more adjacent groups among R2 to R7 may be bonded to each other to form a substituted or unsubstituted aromatic ring having 6 to 20 carbon atoms.

[0081] In one embodiment of the present application, R1 and R8 are each independently hydrogen or deuterium, and R2 to R7 are the same or different and each independently selected from the group consisting of hydrogen, deuterium, and a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, and two or more adjacent groups among R2 to R7 may be bonded to each other to form a substituted or unsubstituted aromatic ring having 6 to 10 carbon atoms.

[0082] In one embodiment of the present application, R1 and R8 are each independently hydrogen or deuterium, R2 to R7 are the same or different and each independently selected from the group consisting of hydrogen, deuterium, and a substituted or unsubstituted phenyl group, and two or more adjacent groups among R2 to R7 may be bonded to each other to form a substituted or unsubstituted benzene ring.

[0083] In one embodiment of the present application, Ar1 in 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 40 carbon atoms and a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.

[0084] In one embodiment of the present application, Ar1 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 40 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms; and 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 40 carbon atoms and a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.

[0085] In one embodiment of the present application, Ar1 may be an amine group substituted or unsubstituted with one or more groups selected from the group consisting of substituted or unsubstituted aryl groups having 6 to 40 carbon atoms and substituted or unsubstituted heteroaryl groups having 2 to 40 carbon atoms.

[0086] In one embodiment of the present application, p in the above Chemical Formula 1 is an integer of 0 to 4, and when p is 2 or more, the substituents in the parentheses are the same or different from each other.

[0087] In one embodiment of the present application, the above-mentioned Chemical Formula 1 may be represented by the following Chemical Formula 2 or Chemical Formula 3.

[0088] [ka] [ka] In the above Chemical Formulae 2 and 3, the definitions of each substituent are the same as those in Chemical Formula 1.

[0089] In one embodiment of the present application, the above-mentioned Chemical Formula 1 may be represented by any one of the following Chemical Formulas 4 to 6.

[0090] [ka] [ka] [ka] In the above Chemical Formulae 4 to 6, the definitions of the respective substituents are the same as those in Chemical Formula 1.

[0091] In one embodiment of the present application, Ar1 in Chemical Formula 1 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 Chemical Formula A below.

[0092] [ka] In the above chemical formula A, L 11 and L 12 are the same or different and each independently represent a direct bond; a substituted or unsubstituted arylene group having 6 to 40 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms, Ar 11 and Ar 12 are the same or different and 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, a and b are 0 or 1; [ka] means the position at which L1 is bonded to the above-mentioned Chemical Formula 1.

[0093] In one embodiment of the present application, L of Formula 1 11 and L 12 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.

[0094] In one embodiment of the present application, the L 11 and L 12may be the same or different and each independently represent a direct bond; or a substituted or unsubstituted arylene group having 6 to 40 carbon atoms.

[0095] In one embodiment of the present application, the L 11 and L 12 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.

[0096] In one embodiment of the present application, the L 11 and L 12 may be the same or different and each independently a direct bond; or a substituted or unsubstituted phenylene group.

[0097] In one embodiment of the present application, the L 11 and L 12 are the same or different and each independently a direct bond; or a phenylene group.

[0098] In one embodiment of the present application, the L 11 is a direct bond.

[0099] In one embodiment of the present application, the L 11 is a phenylene group.

[0100] In one embodiment of the present application, the L 12 is a direct bond.

[0101] In one embodiment of the present application, the L 12 is a phenylene group.

[0102] In one embodiment of the present application, Ar 11 and Ar 12 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.

[0103] In one embodiment of the present application, the Ar 11 and Ar 12 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 groups selected from the group consisting of an alkyl group having 1 to 10 carbon atoms and an aryl group having 6 to 10 carbon atoms; a substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group.

[0104] In one embodiment of the present application, the Ar 11 and Ar 12 may be the same or different and each independently represent a fluorenyl group substituted with one or more groups selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, and a methyl group; a dibenzofuran group; or a dibenzothiophene group.

[0105] In one embodiment of the present application, the Ar 11 and Ar 12 may be identical to each other.

[0106] In one embodiment of the present application, the Ar 11 and Ar 12 may be a substituted or unsubstituted aryl group having 6 to 40 carbon atoms.

[0107] In one embodiment of the present application, the Ar 11 and Ar 12 may each be a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.

[0108] In one embodiment of the present application, the Ar 11 and Ar 12 may be different from each other.

[0109] In one embodiment of the present application, the Ar 11 is a substituted or unsubstituted aryl group having 6 to 40 carbon atoms,12 may be a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.

[0110] In one embodiment of the present application, the Ar 11 is a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms, 12 may be a substituted or unsubstituted aryl group having 6 to 40 carbon atoms.

[0111] The Ar of the formula A may be represented by Ar1 of the formula 1 11 and Ar 12 In the case where one of Ar is an aryl group and the other is a heteroaryl group, the heterocyclic compound represented by the above formula (1) is used as an organic material in an organic light-emitting device, 11 and Ar 12 In the case where both of the Ar are aryl groups, the efficiency and life of the organic light-emitting device are superior to those in the case where both of the Ar are aryl groups. 11 and Ar 12 It is believed that one of the groups is an aryl group and the other is a heteroaryl group, which allows for a stronger charge transfer by further separating the HOMO and LUMO spatially.

[0112] 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:

[0113] [ka] TIFF0007656943000015.tif129161 TIFF0007656943000016.tif135161 TIFF0007656943000017.tif139161 TIFF0007656943000018.tif139161 TIFF0007656943000019.tif138161 TIFF0007656943000020.tif148161 TIFF0007656943000021.tif132161 TIFF0007656943000022.tif157161 TIFF0007656943000023.tif131161 TIFF0007656943000024.tif135161 TIFF0007656943000025.tif132161 TIFF0007656943000026.tif137161 TIFF0007656943000027.tif142161 TIFF0007656943000028.tif144161 TIFF0007656943000029.tif154161 TIFF0007656943000030.tif149161

[0114] 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.

[0115] In addition, by introducing various substituents into the structure of Chemical Formula 1, the energy band gap can be finely adjusted, while improving the properties at the interface between organic materials, thereby diversifying the uses of the material.

[0116] 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.

[0117] 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.

[0118] 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.

[0119] 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.

[0120] In one embodiment of the present application, the first electrode may be an anode and the second electrode may be a cathode.

[0121] In another embodiment of the present application, the first electrode may be a cathode and the second electrode may be an anode.

[0122] 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.

[0123] 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.

[0124] 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.

[0125] The specific details regarding the heterocyclic compound represented by Chemical Formula 1 are the same as those described above.

[0126] 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.

[0127] 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.

[0128] 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.

[0129] 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.

[0130] The organic light-emitting device of the present invention may further include one or more layers selected from the group consisting of a light-emitting layer, a hole-injection layer, a hole-transport layer, an electron-injection layer, an electron-transport layer, an electron-blocking layer, a hole-auxiliary layer, and a hole-blocking layer.

[0131] 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.

[0132] 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.

[0133] 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.

[0134] The organic layer containing the heterocyclic compound represented by Chemical Formula 1 may further contain other substances, if necessary.

[0135] In an organic light-emitting device according to an embodiment of the present application, materials other than the heterocyclic 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.

[0136] The anode material may be a material with a relatively large work function, or may be a transparent conductive oxide, a metal, or a conductive polymer. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

[0137] The cathode material may be a material having a relatively low work function, such as a metal, a metal oxide, or a conductive polymer. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; and materials with a multilayer structure such as LiF / Al or LiO2 / Al.

[0138] 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.

[0139] 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.

[0140] 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.

[0141] As the electron injection material, for example, LiF is typically used in the industry, but the present application is not limited thereto.

[0142] 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.

[0143] 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.

[0144] 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.

[0145] 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.

[0146] 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.

[0147] 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.

[0148] 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.

[0149] 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.

[0150] 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

[0151] 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.

[0152] <Production Example> <Production Example 1> Production of Compounds 1, 14, 28, 198 and 201 1) Preparation of Compound E1 [ka] 2-Bromo-4-chlorodibenzo[b,d]thiophene (20g, 67.2mmol), 9H-carbazole (11.2g, 67.2mmol), CuI (15.8g, 80.6mmol), cyclohexane-1,2-diamine (9.2g, 80.6mmol), K3PO4 (28.4g, 134.4mmol) were placed in a 500ml round-bottom flask, and 1,4-dioxane (200ml) was added, followed by stirring at 140°C. After completion of the reaction, the temperature was lowered to room temperature, and the mixture was concentrated after filtration through Celite. The concentrated reactant was purified with a MC:hexane = 1:3 (v / v) column to obtain compound E1 (23.7g, 61.7mmol, Yield: 91.8%). The MC stands for methylene chloride (hereinafter, MC).

[0153] 2) Preparation of Compound E2 Compound E2 (Yield: 85.1%) was synthesized in the same manner as in the preparation of compound E1, except that A2 in Table 1 below was used instead of 2-bromo-4-chlorodibenzo[b,d]thiophene (A1) in the preparation of compound E1.

[0154] [Table 1]

[0155] 3) Preparation of Compound 1 [ka] E1 (10.0g, 26.0mmol), H1 (6.4g, 26.0mmol), Pd2dba3 (1.2g, 1.3mmol), Xphos (1.2g, 2.6mmol), and NaOtBu (7.5g, 78.0mmol) in Table 2 below were placed in a 500mL round-bottom flask, and xylene (110mL) was added and stirred at 160°C. After completion of the reaction, the temperature was lowered to room temperature, and the mixture was concentrated after filtration through Celite. The concentrated reaction product was purified using a MC:hexane = 1:1 column to obtain compound 1 (14.0g, 23.6mmol, Yield: 90.8%).

[0156] 4) Preparation of Compounds 14, 28, 198 and 201 Compounds 14, 28, 198 and 201 were synthesized in the same manner as in the preparation of compound 1, except that E in Table 2 below was used instead of E1 and H in Table 2 below was used instead of H1.

[0157] [Table 2] TIFF0007656943000035.tif118165

[0158] <Production Example 2> Production of Compounds 55 to 57, 65, 71 to 73, 77, 79, 91, 94 to 96, 98, 111 to 113, 122 to 124, 129, 131, 133, 137, 144, 146, 153 and 160 1) Preparation of compound C3 [ka] 2-Bromodibenzo[b,d]thiophene (20g, 76.0mmol), 9H-carbazole (12.7g, 76.0mmol), CuI (17.8g, 91.2mmol), cyclohexane-1,2-diamine (10.4g, 91.2mmol), K3PO4 (32.2g, 152.0mmol) were placed in a 500ml round-bottom flask, and 1,4-dioxane (200ml) was added and stirred at 140°C. After completion of the reaction, the temperature was lowered to room temperature, and the mixture was concentrated after filtration through Celite. The concentrated reaction product was purified with a MC:hexane = 1:3 (v / v) column to obtain compound C3 (24.2g, 69.3mmol, Yield: 91.2%).

[0159] 2) Preparation of Compounds C4 to C8 Compounds C4 to C8 were synthesized in the same manner as in the production of compound C3, except that in the production of compound C3, A in Table 3 below was used instead of 2-bromodibenzo[b,d]thiophene (A3) and B in Table 3 below was used instead of 9H-carbazole (B1).

[0160] [Table 3] TIFF0007656943000038.tif45165

[0161] 3) Preparation of compound E3 Under a nitrogen atmosphere, C3 (20 g, 57.2 mmol) was placed in a 500 ml round-bottom flask, tetrahydrofuran (hereinafter, THF) (200 ml) was added, and the mixture was stirred at -78°C. Then, 2.5 M n-butyllithium solution (23 ml, 57.2 mmol) was gradually dropped and stirred for 30 minutes. Then, trimethyl borate (9.6 ml, 85.8 mmol) was gradually dropped and stirred. After the reaction was completed, the mixture was extracted with EA / H2O and concentrated. The concentrated reaction product was treated with MgSO4 and concentrated again to obtain compound E3 (19.1 g, 48.6 mmol, Yield: 85.0%).

[0162] 4) Preparation of Compounds E4 to E8 Compounds E4 to E8 were synthesized in the same manner as in the production of compound E3, except that C in Table 4 below was used instead of C3 in the production of compound E3.

[0163] [Table 4] TIFF0007656943000040.tif100165

[0164] 5) Preparation of Compound 57 [ka] E3 (15g, 38.1mmol), H94 (18.1g, 38.1mmol), Pd(PPh3)4 (2.2g, 1.9mmol), K2CO3 (13.1g, 95.3mmol) were placed in a 500ml round bottom flask, 1,4-dioxane / H2O (200ml / 40ml) was added, and the mixture was stirred at 160°C. After completion of the reaction, the temperature was lowered to room temperature, and the mixture was extracted with MC / H2O and concentrated. The concentrated reaction product was purified with MC:hexane = 1:1 (v / v) column to obtain compound 57 (26.3g, 35.3mmol, Yield: 92.7%).

[0165] 6) Preparation of compounds 55, 56, 65, 71-73, 77, 79, 91, 94-96, 98, 111-113, 122-124, 129, 131, 133, 137, 144, 146, 153 and 160 Compounds 55, 56, 64, 71 to 73, 77, 79, 91, 94 to 96, 98, 111 to 113, 122 to 124, 129, 131, 133, 137, 144, 146, 153 and 160 were synthesized in the same manner as in the production of compound 57, except that E in Table 5 below was used instead of E3 and H in Table 5 below was used instead of H94.

[0166] [Table 5] TIFF0007656943000043.tif229165 TIFF0007656943000044.tif228165 TIFF0007656943000045.tif229165 TIFF0007656943000046.tif229165 TIFF0007656943000047.tif230165 TIFF0007656943000048.tif231165 TIFF0007656943000049.tif121165

[0167] The compounds described in the present specification were prepared by the methods of the above Preparation Examples, and the results of confirming the synthesis of the prepared compounds are shown in Tables 6 and 7 below. 1 The values ​​are measured by H NMR (CDCl3, 400 Mz), and the values ​​in Table 7 below are measured by FD-MS (Field desorption mass spectrometry).

[0168] [Table 6] TIFF0007656943000051.tif214165 TIFF0007656943000052.tif221165 TIFF0007656943000053.tif200165 TIFF0007656943000054.tif150165

[0169] [Table 7] TIFF0007656943000056.tif198165 TIFF0007656943000057.tif231165 TIFF0007656943000058.tif231165 TIFF0007656943000059.tif231165 TIFF0007656943000060.tif231165 TIFF0007656943000061.tif232165 TIFF0007656943000062.tif231165 TIFF0007656943000063.tif231165 TIFF0007656943000064.tif231165 TIFF0007656943000065.tif231165

[0170] [Experimental Example] 1) Preparation of organic light-emitting device (red 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.

[0171] 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.

[0172] An emitting layer was formed thereon by thermal vacuum deposition as follows. The emitting layer was formed by using the compound shown in Table 8 below as a host and (piq)2(Ir)(acac) as a red phosphorescent dopant, and the host was doped with 3 wt% of (piq)2(Ir)(acac) and deposited to a thickness of 500 Å. Then, BCP was deposited to a thickness of 60 Å as a hole blocking layer, and Alq3 was deposited to a thickness of 200 Å thereon as an electron transport layer. Then, BCP was deposited to a thickness of 60 Å as a hole blocking layer, and Alq3 was deposited to a thickness of 200 Å thereon as an electron transport layer. Finally, lithium fluoride (LiF) was deposited to a thickness of 10 Å on the electron transport layer to form an electron injection layer, and then an aluminum (Al) cathode was deposited to a thickness of 1,200 Å on the electron injection layer to form a cathode, thereby manufacturing an organic electroluminescent device.

[0173] 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.

[0174] 2) Driving voltage and luminous efficiency of organic electroluminescent devices The electroluminescence (EL) characteristics of the organic electroluminescent device fabricated as described above were measured using a 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 characteristics of the organic electroluminescent device of the present invention are shown in Table 8 below.

[0175] [Table 8] TIFF0007656943000067.tif230165 TIFF0007656943000068.tif231165 TIFF0007656943000069.tif85165

[0176] [ka] From the above experimental examples, it was confirmed that the driving voltage and efficiency can be improved when the heterocyclic compound of Chemical Formula 1 is used as a host in the organic layer, particularly the light-emitting layer, of an organic light-emitting device. Specifically, compared to Comparative Examples 1 to 6, in Examples 1 to 40 using the heterocyclic compound of Chemical Formula 1, the substituents are fixed to have a steric configuration, and the HOMO (highest occupied molecular orbital) and the LUMO (lowest ighest unoccupied molecular orbital) are spatially separated to enable strong charge transfer, making the compound suitable as a red host, and it was confirmed that high efficiency can be expected when used as an organic material in an organic light-emitting device.

[0177] This is believed to be because the C-N bond in the compound of the present application improves drive and efficiency, and the fixing of substituents at specific positions gives it a steric configuration, which spatially separates the HOMO (Highest Occupied Molecular Orbital) and LUMO (HOMO, Lowest ighest Unoccupied Molecular Orbital), enabling strong charge transfer. [Explanation of symbols]

[0178] 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 20】 In the above Chemical Formula 1, L １ is a direct bond; or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, X １ is O; or S, R ｐ is hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; or a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, R １ ~R ８ are the same or different and are each independently selected from the group consisting of hydrogen; deuterium; and a substituted or unsubstituted aryl group having 6 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; Ar １ is a group represented by the following chemical formula A: 【Chemistry 21】 In the above chemical formula A, L 11 and L 12 are the same or different and each independently represents a direct bond; a substituted or unsubstituted arylene group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms; Ar 11 and Ar 12 are the same or different and each independently represents a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms; a1 and b1 are 0 or 1; 【Chemical 22】 means the position at which the group is bonded to L 1 in Chemical Formula 1; a is an integer from 0 to 2, and when a is 2, the substituents in the brackets are the same or different from each other; Each p is an integer of 0 to 4, and when p is 2 or more, the substituents within the brackets are the same or different.

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 formula 1 is represented by the following formula 2 or formula 3: 【Chemistry 23】 【Chemistry 24】 In Chemical Formulae 2 and 3, the definitions of each substituent are the same as in Chemical Formula 1.

4. The heterocyclic compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulas 4 to 6: 【Chemistry 25】 【Chemistry 26】 【Chemical 27】 In the formulae 4 to 6, the definitions of the respective substituents are the same as those in the formula 1.

5. The heterocyclic compound according to claim 1 , wherein the chemical formula 1 is represented by any one of the following compounds: 【Chemistry 28】 【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, an electron-blocking layer, and a hole-blocking layer.

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