Heterocyclic compound, organic light emitting device comprising the same and composition for organic material layer

Abstract

To provide a novel heterocyclic compound, an organic light emitting device including the same, and a composition for an organic material layer.SOLUTION: The present disclosure relates to a heterocyclic compound represented by chemical formula 1, an organic light emitting device including the same, and a composition for an organic material layer.SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to a heterocyclic compound, an organic light-emitting device containing the same, and a composition for an organic layer.

Background Art

[0002] An organic light-emitting device is a type of self-luminous display device, which has advantages such as a wide viewing angle, excellent contrast, and a fast response speed.

[0003] 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 to form a pair in the organic thin film, and then emit light while disappearing. The organic thin film can be configured as a single layer or multiple layers as needed.

[0004] The material of the organic thin film can have a light-emitting function as needed. For example, as the material of the organic thin film, a compound that can itself form a light-emitting layer alone may be used, or a compound that can serve as a host or a dopant in a host-dopant type light-emitting layer may be used. In addition, as the material of the organic thin film, a compound that can serve roles such as hole injection, hole transport, electron blocking, hole blocking, electron transport, and electron injection may be used.

[0005] In order to improve the performance, lifespan, or efficiency of an organic light-emitting device, the development of materials for organic thin films has been continuously demanded.

Prior Art Documents

Patent Documents

[0006]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0007] An object of the present invention is to provide a heterocyclic compound, an organic light-emitting device containing the same, and a composition for an organic layer.

Means for Solving the Problems

[0008] To achieve the above object, The present invention provides a heterocyclic compound represented by the following Chemical Formula 1.

[0009]

Chemical Formula

[0010] In the Chemical Formula 1, R1 to R10 are the same as or different from each other, and each independently is hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1-C60 alkyl group; substituted or unsubstituted C2-C60 alkenyl group; substituted or unsubstituted C2-C60 alkynyl group; substituted or unsubstituted C1-C60 alkoxy group; substituted or unsubstituted C3-C60 cycloalkyl group; substituted or unsubstituted C2-C60 heterocycloalkyl group; Ar1; -P(=O)R101R102; -SiR101R102R103; and are selected from the group consisting of the following Chemical Formula 2, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6-C60 aromatic hydrocarbon ring; or a substituted or unsubstituted C2-C60 heterocyclic ring, and R101, R102, and R103 are the same as or different from each other, and each independently is a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group, Any one of R1 to R10 is the following Chemical Formula 2, and another one is Ar1, Ar1 is a substituted or unsubstituted C6-C60 aryl group; or the following Chemical Formula 3,

Chemical Formula

Chemical Formula

[0011] In addition, the present invention provides an organic light - emitting device including a first electrode, a second electrode provided opposite to the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contain a heterocyclic compound represented by Chemical Formula 1.

[0012] In addition, the present invention provides an organic light - emitting device in which the organic layer further contains a heterocyclic compound represented by the following Chemical Formula 4.

[0013]

Chemical Formula

[0014] In the Chemical Formula 4, R21 to R28 are the same as or different from each other, and each independently is hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1-C60 alkyl group; substituted or unsubstituted C2-C60 alkenyl group; substituted or unsubstituted C2-C60 alkynyl group; substituted or unsubstituted C1-C60 alkoxy group; substituted or unsubstituted C3-C60 cycloalkyl group; substituted or unsubstituted C2-C60 heterocycloalkyl group; -P(=O)R201R202; -SiR201R202R203; the following Chemical Formula 5; the following Chemical Formula 6; and the following Chemical Formula 7, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6-C60 aromatic hydrocarbon ring; or a substituted or unsubstituted C2-C60 heterocyclic ring, and R201, R202 and R203 are the same as or different from each other, and each independently is a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group, Any one of R21 to R28 is the following Chemical Formula 5, and another one is the following Chemical Formula 6; or the following Chemical Formula 7,

Chemical formula

[0015] Moreover, the present invention provides a composition for an organic layer containing the heterocyclic compound represented by the aforesaid Chemical Formula 1 and the heterocyclic compound represented by the aforesaid Chemical Formula 4.

Advantages of the Invention

[0016] The compounds described in this specification can be used as materials for the organic layer of an organic light - emitting device. The aforesaid compounds can serve as a hole injection layer material, a hole transport layer material, a light - emitting layer material, an electron transport layer material, an electron injection layer material, an electron blocking layer material, etc. in an organic light - emitting device.

[0017] In particular, the aforesaid compounds can be used as a hole transport layer material or an electron blocking layer material.

[0018] Moreover, the aforesaid compounds can be used as a light - emitting layer material of an organic light - emitting device. The aforesaid compounds can be used alone as a light - emitting material, and can also be used as a host material or a dopant material of the light - emitting layer. Specifically, the aforesaid compounds can be used alone as a light - emitting material, and can be used as a host material or a dopant material of the light - emitting layer.

[0019] When the heterocyclic compound represented by the aforesaid Chemical Formula 1 is used in the organic layer, the driving voltage of the organic light - emitting device can be reduced, the light - emitting efficiency can be improved, and the lifetime characteristics can be improved.

Brief Description of the Drawings

[0020]

Figure 1

Figure 2

Figure 3

Mode for Carrying Out the Invention

[0021] Hereinafter, the present application will be described in more detail.

[0022] In this specification, the term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced by another substituent, and the position to be substituted is not limited as long as it is the position where the hydrogen atom is substituted, that is, the position where the substituent can be substituted. When two or more substituents are present, the two or more substituents may be the same as or different from each other.

[0023] In this specification, "substituted or unsubstituted" means deuterium; halogen; cyano group; 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 linear, branched or cyclic alkyl group having 1 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; -SiRR'R"; -P(=O)RR'; an alkylamine group having 1 to 20 carbon atoms; a monocyclic or polycyclic arylamine group having 6 to 60 carbon atoms; and a monocyclic or polycyclic heteroarylamine group having 2 to 60 carbon atoms, which is substituted or unsubstituted with one or more substituents selected from the group consisting of, or substituted or unsubstituted with a substituent formed by linking two or more substituents selected from the exemplified substituents, wherein R, R' and R" are the same as or different from each other and are each independently a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; 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.

[0024] In this specification, the halogen may be fluorine, chlorine, bromine or iodine.

[0025] In this specification, the alkyl group includes a straight-chain or branched-chain having 1 to 60 carbon atoms and may be further substituted by other substituents. The number of carbon atoms of the alkyl group may be 1 to 60, specifically 1 to 40, more specifically 1 to 20. Specific examples include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1-ethyl-butyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl-2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, n-octyl group, tert-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group, isohexyl group, 4-methylhexyl group, 5-methylhexyl group, etc., but are not limited thereto.

[0026] In this specification, the alkenyl group includes a straight-chain or branched-chain having 2 to 60 carbon atoms and may be further substituted by other substituents. The number of carbon atoms of the alkenyl group may be 2 to 60, specifically 2 to 40, 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, 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, stilbenyl group, styrenyl group, etc., but are not limited thereto.

[0027] In this specification, the alkynyl group includes a straight-chain or branched-chain having 2 to 60 carbon atoms and may be further substituted by other substituents. The number of carbon atoms of the alkynyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20.

[0028] In this specification, the alkoxy group may be straight-chain, branched-chain or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyl oxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. may be mentioned, but are not limited thereto.

[0029] In this specification, the cycloalkyl group includes a monocyclic or polycyclic having 3 to 60 carbon atoms and may be further substituted by other substituents. Here, the polycyclic means a group in which the cycloalkyl group is directly linked or condensed with another ring group. Here, the other ring group may be a cycloalkyl group, but may also be other types of ring groups, for example, a heterocycloalkyl group, an aryl group, a heteroaryl group, etc. The number of carbon atoms of the cycloalkyl group may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20. Specifically, cyclopropyl group, cyclobutyl group, cyclopentyl group, 3-methylcyclopentyl group, 2,3-dimethylcyclopentyl group, cyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 2,3-dimethylcyclohexyl group, 3,4,5-trimethylcyclohexyl group, 4-tert-butylcyclohexyl group, cycloheptyl group, cyclooctyl group, etc. may be mentioned, but are not limited thereto.

[0030] As used herein, a heterocycloalkyl group contains O, S, Se, N, or Si as a heteroatom, includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted by other substituents. Here, the polycyclic ring means a group in which the heterocycloalkyl group is directly linked or condensed with another ring group. Here, the other ring group may be a heterocycloalkyl group, but may also be other types of ring groups, such as a cycloalkyl group, an aryl group, a heteroaryl group, etc. The carbon number of the heterocycloalkyl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 20.

[0031] As used herein, an aryl group includes a monocyclic or polycyclic ring having 6 to 60 carbon atoms, and may be further substituted by other substituents. Here, the polycyclic ring means a group in which the aryl group is directly linked or condensed with another ring group. Here, the other ring group may be an aryl group, but may also be other types of ring groups, such as a cycloalkyl group, a heterocycloalkyl group, a heteroaryl group, etc. The aryl group may include a spiro group. The carbon number of the aryl group may be 6 to 60, specifically 6 to 40, and more specifically 6 to 20. Specific examples of the aryl group include, but are not limited to, a phenyl group, a biphenyl group, a triphenyl group, a naphthyl group, an anthryl group, a chrysenyl group, a phenanthrenyl group, a ferrenyl 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 these fused ring groups.

[0032] In this specification, the phosphine oxide group is represented by -P(=O)R101R102, where R101 and R102 may be the same as or different from each other and are each 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. Specifically, it may be substituted with an aryl group, and the above examples are applicable to the aryl group. For example, examples of the phosphine oxide group include, but are not limited to, a diphenylphosphine oxide group, a dinaphthylphosphine oxide, etc.

[0033] In this specification, the silyl group contains Si and is a substituent in which the Si atom is directly linked as a radical, represented by -SiR101R102R103, where R101 to R103 may be the same as or different from each other and are each 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, a phenylsilyl group, etc.

[0034] In this specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

[0035] When the fluorenyl group is substituted,

Chemical formula

[0036] In this specification, the spiro group is a group containing a spiro structure and may have 15 to 60 carbon atoms. For example, the spiro group may contain a structure in which a 2,3-dihydro-1H-indenyl group or a cyclohexane group is spiro-bonded to a fluorenyl group. Specifically, the following spiro group may contain any one of the groups represented by the following structural formulas.

Chemical formula

[0037] In this specification, a heteroaryl group contains S, O, Se, N, or Si as a heteroatom, contains a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted by other substituents. Here, the polycyclic ring means a group in which a heteroaryl group is directly linked or condensed with another ring group. Here, the other ring group may be a heteroaryl group, but may also be other types of ring groups, such as a cycloalkyl group, a heterocycloalkyl group, an aryl group, and the like. The number of carbon atoms of the heteroaryl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 25.Specific examples of the heteroaryl group include a pyridyl group, a pyrrolyl group, a pyrimidyl group, a pyridazinyl group, a furanyl group, a thiophenyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, a furazanyl group, an oxadiazolyl group, a thiadiazolyl group, a dithiazolyl group, a tetrazolyl group, a pyranyl group, a thiopyranyl group, a diazinyl group, an oxazinyl group, a thiazinyl group, a dioxinyl group, a triazinyl group, a tetrazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, an isoquinazolinyl group, a quinozolilyl group, a naphthyridyl group, an acridinyl group, a phenanthridinyl group, an imidazopyridinyl group, a diazanaphthalenyl group, a triazaindenyl, a 2-indolyl group, an indolizinyl group, a benzothiazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiophenyl group, a benzofuranyl group, a dibenzothiophenyl group, a dibenzofuranyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a phenazinyl group, a dibenzosilol group, spirobi(dibenzosilol), a dihydrophenazinyl group, a phenoxazinyl group, a phenanthridyl group, a thienyl group, an indolo[2,3-a]carbazolyl group, an indolo[2,3-b]carbazolyl group, an indolinyl group, a 10,11-dihydro-dibenzo[b,f]azepinyl group, a 9,10-dihydroacridinyl group, a phenanthradinyl group, a phenothiatiazinyl group, a phthalazinyl group, a naphthyridinyl group, a phenanthrolinyl group, a benzo[c][1,2,5]thiadiazolyl group, a 5,10-dihydrodibenzo[b,e][1,4]azasilinyl group, a pyrazolo[1,5-c]quinazolinyl group, a pyrido[1,2-b]indazolyl group, a pyrido[1,2-a]imidazo[1,2-e]indolinyl group, a 5,11-dihydroindenol[1,2-b]carbazolyl group, and the like, but are not limited thereto.

[0038] 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. 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, a biphenyltriphenylenylamine group, and the like, but are not limited thereto.

[0039] In this specification, the arylene group means a group having two bonding positions on the aryl group, that is, a divalent group. The descriptions of the aforementioned aryl groups apply to these, except that they are each divalent groups. Further, the heteroarylene group means a group having two bonding positions on the heteroaryl group, that is, a divalent group. The descriptions of the aforementioned heteroaryl groups apply to these, except that they are each divalent groups.

[0040] In this specification, the "adjacent" group may mean a substituent substituted on an atom directly connected to the atom substituted with the substituent, a substituent that is sterically closest to the substituent, or another substituent substituted on the atom substituted with the substituent. For example, two substituents substituted at the ortho position on a benzene ring and two substituents substituted at the same carbon on an aliphatic ring can be interpreted as "adjacent" groups to each other.

[0041] In the present invention, "when no substituent is shown in the chemical formula or compound structure" means that a hydrogen atom is bonded to a carbon atom. However, since deuterium (< 2 H, Deuterium (D)) is an isotope of hydrogen, some of the hydrogen atoms may be deuterium.

[0042] In one embodiment of the present invention, "when no substituent is shown in the chemical formula or compound structure" may mean that all positions where a substituent can be introduced are hydrogen or deuterium. That is, in the case of deuterium, as an isotope of hydrogen, some of the hydrogen atoms may be deuterium, which is an isotope, and at this time, the deuterium content may be 0% to 100%.

[0043] In one embodiment of the present invention, in the case of "when no substituent is shown in the chemical formula or compound structure", when deuterium is not explicitly excluded, such as "the deuterium content is 0%", "the hydrogen content is 100%", "all substituents are hydrogen", etc., hydrogen and deuterium may be used mixedly in the compound.

[0044] In one embodiment of the present invention, deuterium is one of the isotopes of hydrogen, and is an element having a deuteron composed of 1 proton and 1 neutron as its nucleus, and hydrogen -2 can be represented by, and the element symbol can also be represented by D or 2 H.

[0045] In one embodiment of the present invention, an isotope can also be interpreted as an element having the same atomic number (Z) but different mass numbers (A), which has the same number of protons but different numbers of neutrons.

[0046] In one embodiment of the present invention, the meaning of the content T% of a specific substituent can be defined as follows: when the total number of substituents that the base compound can have is defined as T1, and the number of a specific substituent among them is defined as T2, then T2 / T1×100 = T% can be defined.

[0047] That is, in one example,

Chemical formula

[0048]

Chemical formula

[0049] Also, in one embodiment of the present invention, the case of "a phenyl group with a deuterium content of 0%" may mean a phenyl group that does not contain deuterium atoms, that is, a phenyl group having 5 hydrogen atoms.

[0050] In the present invention, the C6 - C60 aromatic hydrocarbon ring means a compound containing an aromatic ring composed of C6 - C60 carbon and hydrogen atoms. For example, phenyl, biphenyl, terphenyl, triphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, azulene, etc. can be mentioned, but it is not limited to these. As long as the carbon number is satisfied, all aromatic hydrocarbon ring compounds known in this field are included.

[0051] The present invention provides a heterocyclic compound represented by the following Chemical formula 1.

Chemical formula

[0052] In the above Chemical Formula 1, R1 to R10 are the same as or different from each other, and each independently is hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1-C60 alkyl group; substituted or unsubstituted C2-C60 alkenyl group; substituted or unsubstituted C2-C60 alkynyl group; substituted or unsubstituted C1-C60 alkoxy group; substituted or unsubstituted C3-C60 cycloalkyl group; substituted or unsubstituted C2-C60 heterocycloalkyl group; Ar1; -P(=O)R101R102; -SiR101R102R103; or selected from the group consisting of the following Chemical Formula 2, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6-C60 aromatic hydrocarbon ring; or a substituted or unsubstituted C2-C60 heterocyclic ring, and R101, R102, and R103 are the same as or different from each other, and each independently is a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group, Any one of R1 to R10 is the following Chemical Formula 2, and another one is Ar1, Ar1 is a substituted or unsubstituted C6-C60 aryl group; or the following Chemical Formula 3,

Chemical formula

[0053] In one embodiment of the present invention, R1 to R10 are the same as or different from each other, and each independently is hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1-C30 alkyl group; substituted or unsubstituted C2-C30 alkenyl group; substituted or unsubstituted C2-C30 alkynyl group; substituted or unsubstituted C1-C30 alkoxy group; substituted or unsubstituted C3-C30 cycloalkyl group; substituted or unsubstituted C2-C30 heterocycloalkyl group; Ar1; -P(=O)R101R102; -SiR101R102R103; or the chemical formula 2, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6-C30 aromatic hydrocarbon ring; or a substituted or unsubstituted C2-C30 heterocycle, wherein R101, R102 and R103 are the same as or different from each other, and each independently is a substituted or unsubstituted C1-C30 alkyl group; a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C2-C30 heteroaryl group, and any one of R1 to R10 may be the chemical formula 2, and another one may be Ar1.

[0054] In another embodiment of the present invention, R1 to R10 are the same as or different from each other, and each independently is hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1-C20 alkyl group; substituted or unsubstituted C2-C20 alkenyl group; substituted or unsubstituted C2-C20 alkynyl group; substituted or unsubstituted C1-C20 alkoxy group; substituted or unsubstituted C3-C20 cycloalkyl group; substituted or unsubstituted C2-C20 heterocycloalkyl group; Ar1; -P(=O)R101R102; -SiR101R102R103; or the chemical formula 2, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6-C20 aromatic hydrocarbon ring; or a substituted or unsubstituted C2-C20 heterocycle, and R101, R102 and R103 are the same as or different from each other, and each independently is a substituted or unsubstituted C1-C20 alkyl group; a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group, and any one of R1 to R10 may be the chemical formula 2, and another one may be Ar1.

[0055] In another embodiment of the present invention, R1 to R10 are the same as or different from each other, and each independently is hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1-C20 alkyl group; substituted or unsubstituted C2-C20 alkenyl group; substituted or unsubstituted C2-C20 alkynyl group; substituted or unsubstituted C1-C20 alkoxy group; substituted or unsubstituted C3-C20 cycloalkyl group; substituted or unsubstituted C2-C20 heterocycloalkyl group; Ar1; -P(=O)R101R102; -SiR101R102R103; or the chemical formula 2, and R101, R102 and R103 are the same as or different from each other, and each independently is a substituted or unsubstituted C1-C20 alkyl group; a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group, and any one of R1 to R10 may be the chemical formula 2, and another one may be Ar1.

[0056] In another embodiment of the present invention, R1 to R10 may be the same as or different from each other, and each independently may be hydrogen; deuterium; Ar1; or the chemical formula 2, and any one of R1 to R10 may be the chemical formula 2, and another one may be Ar1.

[0057] In another embodiment of the present invention, R1 to R10 may be the same as or different from each other, and each independently may be hydrogen; deuterium; Ar1; or the chemical formula 2, R1 may be the chemical formula 2, and any one of R7 to R10 may be Ar1, and the rest may be hydrogen; or deuterium.

[0058] In another embodiment of the present invention, R1 to R10 may be the same as or different from each other, and each independently may be hydrogen; deuterium; Ar1; or the chemical formula 2, R2 may be the chemical formula 2, and any one of R7 to R10 may be Ar1, and the rest may be hydrogen; or deuterium.

[0059] In another embodiment of the present invention, R1 to R10 may be the same as or different from each other, and each independently may be hydrogen; deuterium; Ar1; or the chemical formula 2, R3 may be the chemical formula 2, and any one of R7 to R10 may be Ar1, and the rest may be hydrogen; or deuterium.

[0060] In another embodiment of the present invention, R1 to R10 may be the same as or different from each other, and each independently may be hydrogen; deuterium; Ar1; or the chemical formula 2, R4 may be the chemical formula 2, and any one of R7 to R10 may be Ar1, and the rest may be hydrogen; or deuterium.

[0061] In another embodiment of the present invention, R1 to R10 may be the same as or different from each other, and each independently may be hydrogen; deuterium; Ar1; or the chemical formula 2, R5 may be the chemical formula 2, and any one of R7 to R10 may be Ar1, and the rest may be hydrogen; or deuterium.

[0062] In another embodiment of the present invention, R1 to R10 may be the same as or different from each other, and each independently may be hydrogen; deuterium; Ar1; or the chemical formula 2, R6 is the chemical formula 2, and any one of R9 and R10 is Ar1, and the rest may be hydrogen; or deuterium.

[0063] In another embodiment of the present invention, R1 to R10 may be the same as or different from each other, and each independently may be hydrogen; deuterium; Ar1; or the chemical formula 2, R7 is the chemical formula 2, and any one of R1 to R5, R9 and R10 is Ar1, and the rest may be hydrogen; or deuterium.

[0064] In another embodiment of the present invention, R1 to R10 may be the same as or different from each other, and each independently may be hydrogen; deuterium; Ar1; or the chemical formula 2, R8 is the chemical formula 2, and any one of R1 to R6 and R10 is Ar1, and the rest may be hydrogen; or deuterium.

[0065] In another embodiment of the present invention, R1 to R10 may be the same as or different from each other, and each independently may be hydrogen; deuterium; Ar1; or the chemical formula 2, R9 is the chemical formula 2, and any one of R1 to R7 is Ar1, and the rest may be hydrogen; or deuterium.

[0066] In another embodiment of the present invention, R1 to R10 may be the same as or different from each other, and each independently may be hydrogen; deuterium; Ar1; or the chemical formula 2, R10 is the chemical formula 2, and any one of R1 to R8 is Ar1, and the rest may be hydrogen; or deuterium.

[0067] In one embodiment of the present invention, Ar1 may be a substituted or unsubstituted C6 - C30 aryl group; or the chemical formula 3.

[0068] In another embodiment of the present invention, Ar1 may be a substituted or unsubstituted C6-C20 aryl group; or may be the chemical formula 3.

[0069] In another embodiment of the present invention, Ar1 may be a substituted or unsubstituted phenyl group; or may be the chemical formula 3.

[0070] In one embodiment of the present invention, L1 to L3 may be the same as or different from each other, and each independently may be a direct bond; a substituted or unsubstituted C6-C30 arylene group; or a substituted or unsubstituted C2-C30 heteroarylene group.

[0071] In another embodiment of the present invention, L1 to L3 may be the same as or different from each other, and each independently may be a direct bond; a substituted or unsubstituted C6-C20 arylene group; or a substituted or unsubstituted C2-C20 heteroarylene group.

[0072] In another embodiment of the present invention, L1 to L3 may be the same as or different from each other, and each independently may be a direct bond; or a substituted or unsubstituted C6-C60 arylene group.

[0073] In another embodiment of the present invention, L1 to L3 may be the same as or different from each other, and each independently may be a direct bond; or a substituted or unsubstituted C6-C30 arylene group.

[0074] In another embodiment of the present invention, L1 to L3 may be the same as or different from each other, and each independently may be a direct bond; or a substituted or unsubstituted C6-C20 arylene group.

[0075] In another embodiment of the present invention, L1 may be a direct bond.

[0076] In another embodiment of the present invention, L2 and L3 may be the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted C6-C60 arylene group.

[0077] In another embodiment of the present invention, L2 and L3 may be the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted C6-C30 arylene group.

[0078] In another embodiment of the present invention, L2 and L3 may be the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted C6-C20 arylene group.

[0079] In another embodiment of the present invention, L2 and L3 may be the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted non-phenylene group.

[0080] In one embodiment of the present invention, Ar2 and Ar3 may be the same as or different from each other, and each independently a substituted or unsubstituted C6-C30 aryl group; or the chemical formula 3.

[0081] In another embodiment of the present invention, Ar2 and Ar3 may be the same as or different from each other, and each independently a substituted or unsubstituted C6-C20 aryl group; or the chemical formula 3.

[0082] In another embodiment of the present invention, Ar2 and Ar3 may be the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrenyl group; or the chemical formula 3.

[0083] In one embodiment of the present invention, Ar1 is the chemical formula 3, and Ar2 and Ar3 may be a substituted or unsubstituted C6-C60 aryl group.

[0084] In another embodiment of the present invention, Ar1 is the chemical formula 3, and Ar2 and Ar3 may be a substituted or unsubstituted C6-C30 aryl group.

[0085] In another embodiment of the present invention, Ar1 is the chemical formula 3, and Ar2 and Ar3 may be a substituted or unsubstituted C6-C20 aryl group.

[0086] In another embodiment of the present invention, Ar1 is the chemical formula 3, and Ar2 and Ar3 may be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted phenanthrenyl group.

[0087] In another embodiment of the present invention, Ar1 is a substituted or unsubstituted C6-C60 aryl group, one of Ar2 and Ar3 is a substituted or unsubstituted C6-C60 aryl group, and the other may be the chemical formula 3.

[0088] In another embodiment of the present invention, Ar1 is a substituted or unsubstituted C6-C30 aryl group, one of Ar2 and Ar3 is a substituted or unsubstituted C6-C30 aryl group, and the other may be the chemical formula 3.

[0089] In another embodiment of the present invention, Ar1 is a substituted or unsubstituted C6-C20 aryl group, one of Ar2 and Ar3 is a substituted or unsubstituted C6-C20 aryl group, and the other may be the chemical formula 3.

[0090] In another embodiment of the present invention, Ar1 is a substituted or unsubstituted phenyl group, and one of Ar2 and Ar3 is a substituted or unsubstituted phenyl group; or a substituted or unsubstituted non-phenyl group, and the other may be the chemical formula 3.

[0091] In one embodiment of the present invention, Ar4 may be a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C2-C30 heteroaryl group.

[0092] In another embodiment of the present invention, Ar4 may be a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group.

[0093] In another embodiment of the present invention, Ar4 may be a substituted or unsubstituted C6-C60 aryl group.

[0094] In another embodiment of the present invention, Ar4 may be a substituted or unsubstituted C6-C30 aryl group.

[0095] In another embodiment of the present invention, Ar4 may be a substituted or unsubstituted C6-C20 aryl group.

[0096] In another embodiment of the present invention, Ar4 may be a substituted or unsubstituted phenyl group.

[0097] In one embodiment of the present invention, R11 and R12 are the same as or different from each other, and each independently is hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1-C30 alkyl group; substituted or unsubstituted C2-C30 alkenyl group; substituted or unsubstituted C2-C30 alkynyl group; substituted or unsubstituted C1-C30 alkoxy group; substituted or unsubstituted C3-C30 cycloalkyl group; substituted or unsubstituted C2-C30 heterocycloalkyl group; substituted or unsubstituted C6-C30 aryl group; substituted or unsubstituted C2-C30 heteroaryl group; -P(=O)R101R102; -SiR101R102R103; or -NR101R102, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6-C30 aromatic hydrocarbon ring; or a substituted or unsubstituted C2-C30 heterocycle, and R101, R102, and R103 are the same as or different from each other, and each independently may be a substituted or unsubstituted C1-C30 alkyl group; a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C2-C30 heteroaryl group.

[0098] In another embodiment of the present invention, R11 and R12 are the same as or different from each other, and each independently is hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1-C20 alkyl group; substituted or unsubstituted C2-C20 alkenyl group; substituted or unsubstituted C2-C20 alkynyl group; substituted or unsubstituted C1-C20 alkoxy group; substituted or unsubstituted C3-C20 cycloalkyl group; substituted or unsubstituted C2-C20 heterocycloalkyl group; substituted or unsubstituted C6-C20 aryl group; substituted or unsubstituted C2-C20 heteroaryl group; -P(=O)R101R102; -SiR101R102R103; or -NR101R102, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6-C20 aromatic hydrocarbon ring; or a substituted or unsubstituted C2-C20 heterocyclic ring, and R101, R102 and R103 are the same as or different from each other, and each independently may be a substituted or unsubstituted C1-C20 alkyl group; a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group.

[0099] In another embodiment of the present invention, R11 and R12 are the same as or different from each other, and each independently is hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1-C20 alkyl group; substituted or unsubstituted C2-C20 alkenyl group; substituted or unsubstituted C2-C20 alkynyl group; substituted or unsubstituted C1-C20 alkoxy group; substituted or unsubstituted C3-C20 cycloalkyl group; substituted or unsubstituted C2-C20 heterocycloalkyl group; substituted or unsubstituted C6-C20 aryl group; substituted or unsubstituted C2-C20 heteroaryl group; -P(=O)R101R102; -SiR101R102R103; or -NR101R102, and R101, R102 and R103 are the same as or different from each other, and each independently may be a substituted or unsubstituted C1-C20 alkyl group; a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group.

[0100] In another embodiment of the present invention, R11 and R12 may be the same as or different from each other, and each independently may be hydrogen; deuterium; a halogen; a cyano group; a substituted or unsubstituted C1-C20 alkyl group; a substituted or unsubstituted C2-C20 alkenyl group; a substituted or unsubstituted C2-C20 alkynyl group; a substituted or unsubstituted C1-C20 alkoxy group; a substituted or unsubstituted C3-C20 cycloalkyl group; a substituted or unsubstituted C2-C20 heterocycloalkyl group; a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group.

[0101] In another embodiment of the present invention, R11 and R12 may be the same as or different from each other, and each independently may be hydrogen; deuterium; a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group.

[0102] In another embodiment of the present invention, R11 and R12 may be the same as or different from each other, and each independently may be hydrogen; or deuterium.

[0103] In one embodiment of the present invention, the heterocyclic compound represented by Chemical Formula 1 may be represented by any one of the following Chemical Formulas 1-1 to 1-3.

[0104]

Chem.

[0105]

Chem.

[0106]

Chem.

[0107] In the above Chemical Formulas 1-1 to 1-3, R13 to R16 are the same as or different from each other, and each independently is hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1-C60 alkyl group; substituted or unsubstituted C2-C60 alkenyl group; substituted or unsubstituted C2-C60 alkynyl group; substituted or unsubstituted C1-C60 alkoxy group; substituted or unsubstituted C3-C60 cycloalkyl group; substituted or unsubstituted C2-C60 heterocycloalkyl group; substituted or unsubstituted C6-C60 aryl group; substituted or unsubstituted C2-C60 heteroaryl group; -P(=O)R101R102; -SiR101R102R103; and -NR101R102, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6-C60 aromatic hydrocarbon ring; or a substituted or unsubstituted C2-C60 heterocyclic ring, and R101, R102 and R103 are the same as or different from each other, and each independently is a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group, f is an integer from 0 to 5, and when f is 2 or more, R13 are the same as or different from each other, g is an integer from 0 to 3, and when g is 2 or more, R14 are the same as or different from each other, h is an integer from 0 to 6, and when h is 2 or more, R15 are the same as or different from each other, i is an integer from 0 to 2, and when i is 2 or more, R16 are the same as or different from each other, Ar1 is the same as the definition in Chemical Formula 1, L1 to L3, Ar2, Ar3 and a to c are the same as the definitions in Chemical Formula 2.

[0108] In one embodiment of the present invention, R13 to R16 are the same as or different from each other, and each independently is hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1-C30 alkyl group; substituted or unsubstituted C2-C30 alkenyl group; substituted or unsubstituted C2-C30 alkynyl group; substituted or unsubstituted C1-C30 alkoxy group; substituted or unsubstituted C3-C30 cycloalkyl group; substituted or unsubstituted C2-C30 heterocycloalkyl group; substituted or unsubstituted C6-C30 aryl group; substituted or unsubstituted C2-C30 heteroaryl group; -P(=O)R101R102; -SiR101R102R103; or -NR101R102, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6-C30 aromatic hydrocarbon ring; or a substituted or unsubstituted C2-C30 heterocycle, and R101, R102 and R103 are the same as or different from each other, and each independently may be a substituted or unsubstituted C1-C30 alkyl group; a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C2-C30 heteroaryl group.

[0109] In another embodiment of the present invention, R13 to R16 are the same as or different from each other, and each independently is hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1-C20 alkyl group; substituted or unsubstituted C2-C20 alkenyl group; substituted or unsubstituted C2-C20 alkynyl group; substituted or unsubstituted C1-C20 alkoxy group; substituted or unsubstituted C3-C20 cycloalkyl group; substituted or unsubstituted C2-C20 heterocycloalkyl group; substituted or unsubstituted C6-C20 aryl group; substituted or unsubstituted C2-C20 heteroaryl group; -P(=O)R101R102; -SiR101R102R103; or -NR101R102, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6-C20 aromatic hydrocarbon ring; or a substituted or unsubstituted C2-C20 heterocyclic ring, and R101, R102 and R103 are the same as or different from each other, and each independently is a substituted or unsubstituted C1-C20 alkyl group; a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group.

[0110] In another embodiment of the present invention, R13 to R16 are the same as or different from each other, and each independently is hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1-C20 alkyl group; substituted or unsubstituted C2-C20 alkenyl group; substituted or unsubstituted C2-C20 alkynyl group; substituted or unsubstituted C1-C20 alkoxy group; substituted or unsubstituted C3-C20 cycloalkyl group; substituted or unsubstituted C2-C20 heterocycloalkyl group; substituted or unsubstituted C6-C20 aryl group; substituted or unsubstituted C2-C20 heteroaryl group; -P(=O)R101R102; -SiR101R102R103; or -NR101R102, and R101, R102 and R103 are the same as or different from each other, and each independently is a substituted or unsubstituted C1-C20 alkyl group; a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group.

[0111] In another embodiment of the present invention, R13 to R16 may be the same as or different from each other, and each independently may be hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1-C20 alkyl group; substituted or unsubstituted C2-C20 alkenyl group; substituted or unsubstituted C2-C20 alkynyl group; substituted or unsubstituted C1-C20 alkoxy group; substituted or unsubstituted C3-C20 cycloalkyl group; substituted or unsubstituted C2-C20 heterocycloalkyl group; substituted or unsubstituted C6-C20 aryl group; or substituted or unsubstituted C2-C20 heteroaryl group.

[0112] In another embodiment of the present invention, R13 to R16 may be the same as or different from each other, and each independently may be hydrogen; deuterium; substituted or unsubstituted C6-C20 aryl group; or substituted or unsubstituted C2-C20 heteroaryl group.

[0113] In another embodiment of the present invention, R13 to R16 may be the same as or different from each other, and each independently may be hydrogen; or deuterium.

[0114] In one embodiment of the present invention, R1 to R16, Ar1 to Ar4, and L1 to L3 may all contain non-deuterated hydrogen (H).

[0115] In another embodiment of the present invention, at least one of R1 to R16, Ar1 to Ar4, and L1 to L3 may contain deuterium (D), and at least one of R1 to R16, Ar1 to Ar4, and L1 to L3 may contain non-deuterated hydrogen.

[0116] In another embodiment of the present invention, R1 to R16, Ar1 to Ar4, and L1 to L3 may all contain deuterium.

[0117] In one embodiment of the present invention, the heterocyclic compound represented by Chemical Formula 1 does not contain deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be, for example, more than 0%, 1% or more, 10% or more, 20% or more, 30% or more, 40% or more, or 50% or more, and may also be 100% or less, 90% or less, 80% or less, 70% or less, or 60% or less.

[0118] In another embodiment of the present invention, the heterocyclic compound represented by Chemical Formula 1 does not contain deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be 1% to 100%.

[0119] In another embodiment of the present invention, the heterocyclic compound represented by Chemical Formula 1 does not contain deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be 20% to 90%.

[0120] In another embodiment of the present invention, the heterocyclic compound represented by Chemical Formula 1 does not contain deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be 30% to 80%.

[0121] In another embodiment of the present invention, the heterocyclic compound represented by Chemical Formula 1 does not contain deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be 50% to 70%.

[0122] In one embodiment of the present invention, the heterocyclic compound represented by Chemical Formula 1 may be represented by any one of the following compounds.

[0123]

Chemical formula

[0124]

Chemical formula

[0125]

Chem.

[0126]

Chem.

[0127]

Chem.

[0128]

Chem.

[0129]

Chem.

[0130]

Chem.

[0131]

Chem.

[0132]

Chem.

[0133]

Chem.

[0134]

Chem.

[0135]

Chem.

[0136]

Chem.

[0137]

Chem.

[0138]

Chem.

[0139]

Chem.

[0140]

Chem.

[0141]

Chem.

[0142]

Chem.

[0143]

Chem.

[0144]

Chem.

[0145]

Chem.

[0146] [Chemistry]

[0147] [Chemistry]

[0148] [Chemistry]

[0149] [Chemistry]

[0150] In addition, by introducing various substituents into the heterocyclic compound represented by the chemical formula 1, compounds having the unique properties of the introduced substituents can be synthesized. For example, by introducing substituents mainly used for hole injection layer materials, hole transport layer materials, light-emitting layer materials, electron transport layer materials, electron blocking layer materials, and charge generation layer materials used in the manufacture of organic light-emitting devices into the core structure, substances that meet the requirements of each organic layer can be synthesized.

[0151] In addition, by introducing various substituents into the heterocyclic compound represented by the chemical formula 1, fine adjustment of the energy band gap can be enabled, while improving the properties at the interface between organic substances and diversifying the uses of the substances.

[0152] On the other hand, the heterocyclic compound has a high glass transition temperature (Tg) and excellent thermal stability. Such an improvement in thermal stability is an important factor in providing driving stability to the device.

[0153] The heterocyclic compound according to an embodiment of the present invention may be produced by a multi-step chemical reaction. Some intermediate compounds may be first produced, and the heterocyclic compound represented by Chemical Formula 1 may be produced from the intermediate compounds. More specifically, the heterocyclic compound according to an embodiment of the present invention may be produced based on the production examples described later.

[0154] Another embodiment of the present invention provides an organic light-emitting device including the heterocyclic compound represented by Chemical Formula 1. The "organic light-emitting device" can be expressed by terms such as "organic light-emitting diode", "OLED (Organic Light Emitting Diodes)", "OLED device", and "organic electroluminescent device".

[0155] Further, the present invention a first electrode, a second electrode provided to face the first electrode, and an organic light-emitting device including one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contain the heterocyclic compound represented by Chemical Formula 1. The present invention relates to an organic light-emitting device.

[0156] In one embodiment of the present invention, the first electrode may be a positive electrode, and the second electrode may be a negative electrode.

[0157] In another embodiment, the first electrode may be a negative electrode, and the second electrode may be a positive electrode.

[0158] In one embodiment of the present invention, the organic light-emitting device may be a red organic light-emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material for a red organic light-emitting material.

[0159] In another embodiment of the present invention, the organic light-emitting device may be a blue organic light-emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material for a blue organic light-emitting material.

[0160] In another embodiment of the present invention, the organic light-emitting device may be a green organic light-emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material for a green organic light-emitting material.

[0161] In one embodiment of the present invention, the organic light-emitting device may be a red organic light-emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a light-emitting layer material of the red organic light-emitting device.

[0162] In another embodiment of the present invention, the organic light-emitting device may be a blue organic light-emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a light-emitting layer material of the blue organic light-emitting device.

[0163] In another embodiment of the present invention, the organic light-emitting device may be a green organic light-emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a light-emitting layer material of the green organic light-emitting device.

[0164] The specific content of the heterocyclic compound represented by Chemical Formula 1 is as described above.

[0165] The organic light-emitting device of the present invention can be manufactured by the manufacturing methods and materials of ordinary organic light-emitting devices, except that one or more organic layers are formed using the above-described heterocyclic compound.

[0166] The heterocyclic compound can be formed as an organic layer by not only a vacuum evaporation method but also a solution coating method during the manufacture of the organic light-emitting device. Here, the solution coating method means spin coating, dip coating, inkjet printing, screen printing, spraying method, roll coating, etc., but is not limited thereto.

[0167] The organic layer of the organic light-emitting device of the present invention may be configured in a single-layer structure, or may be configured in a multilayer structure in which two or more organic layers are stacked. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, an electron blocking layer, a hole transport layer, a light-emitting layer, an electron transport layer, a hole blocking layer, an electron injection layer, etc. as the organic layer. However, the structure of the organic light-emitting device is not limited thereto, and it may include a smaller number of organic layers.

[0168] In the organic light-emitting device of the present invention, the organic layer includes a light-emitting layer, and the light-emitting layer may include the heterocyclic compound represented by Chemical Formula 1. When the heterocyclic compound is used in the light-emitting layer, since the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) are spatially separated and strong charge transfer is possible, the driving efficiency and lifetime of the organic light-emitting device may be improved.

[0169] An organic light-emitting device according to an embodiment of the present invention provides an organic light-emitting device in which the organic layer containing the heterocyclic compound represented by Chemical Formula 1 further includes the heterocyclic compound represented by the following Chemical Formula 4.

[0170] [Chemical Formula]

[0171] In the Chemical Formula 4, R21 to R28 are the same as or different from each other, and each independently is hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1-C60 alkyl group; substituted or unsubstituted C2-C60 alkenyl group; substituted or unsubstituted C2-C60 alkynyl group; substituted or unsubstituted C1-C60 alkoxy group; substituted or unsubstituted C3-C60 cycloalkyl group; substituted or unsubstituted C2-C60 heterocycloalkyl group; -P(=O)R201R202; -SiR201R202R203; the following Chemical Formula 5; the following Chemical Formula 6; and the following Chemical Formula 7, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6-C60 aromatic hydrocarbon ring; or a substituted or unsubstituted C2-C60 heterocycle, wherein R201, R202 and R203 are the same as or different from each other, and each independently is a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group, Any one of R21 to R28 is the following Chemical Formula 5, and another one is the following Chemical Formula 6; or the following Chemical Formula 7,

Chemical formula

[0172] In the Chemical Formulas 5 to 7, L11 to L16 are the same as or different from each other, and each independently is a direct bond; a substituted or unsubstituted C6-C60 arylene group, or a substituted or unsubstituted C2-C60 heteroarylene group, j is an integer from 0 to 5. When j is 2 or more, L11 are the same as or different from each other, k is an integer from 0 to 5. When k is 2 or more, L12 are the same as or different from each other, l is an integer from 0 to 5. When l is 2 or more, L13 are the same as or different from each other, m is an integer from 0 to 5. When m is 2 or more, L14 are the same as or different from each other, Said n is an integer from 0 to 5, and when n is 2 or more, L15 are the same as or different from each other, Said o is an integer from 0 to 5, and when o is 2 or more, L16 are the same as or different from each other, Said Ar11 to Ar15 are the same as or different from each other, and each independently is a substituted or unsubstituted C6 - C60 aryl group; or a substituted or unsubstituted C2 - C60 heteroaryl group.

[0173] In one embodiment of the present invention, said R21 to R28 are the same as or different from each other, and each independently is hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 - C30 alkyl group; substituted or unsubstituted C2 - C30 alkenyl group; substituted or unsubstituted C2 - C30 alkynyl group; substituted or unsubstituted C1 - C30 alkoxy group; substituted or unsubstituted C3 - C30 cycloalkyl group; substituted or unsubstituted C2 - C30 heterocycloalkyl group; -P(=O)R201R202; -SiR201R202R203; said Chemical Formula 5; said Chemical Formula 6; or said Chemical Formula 7, or two or more adjacent groups among them are bonded to each other to form a substituted or unsubstituted C6 - C30 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 - C30 heterocyclic ring, and said R201, R202 and R203 are the same as or different from each other, and each independently may be a substituted or unsubstituted C1 - C30 alkyl group; a substituted or unsubstituted C6 - C30 aryl group; or a substituted or unsubstituted C2 - C30 heteroaryl group, and any one of said R21 to R28 may be said Chemical Formula 5, and another one may be said Chemical Formula 6; or said Chemical Formula 7.

[0174] In another embodiment of the present invention, R21 to R28 may be the same as or different from each other, and each independently is hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1-C20 alkyl group; substituted or unsubstituted C2-C20 alkenyl group; substituted or unsubstituted C2-C20 alkynyl group; substituted or unsubstituted C1-C20 alkoxy group; substituted or unsubstituted C3-C20 cycloalkyl group; substituted or unsubstituted C2-C20 heterocycloalkyl group; -P(=O)R201R202; -SiR201R202R203; the chemical formula 5; the chemical formula 6; or the chemical formula 7, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6-C20 aromatic hydrocarbon ring; or a substituted or unsubstituted C2-C20 heterocyclic ring, and R201, R202 and R203 may be the same as or different from each other, and each independently is a substituted or unsubstituted C1-C20 alkyl group; a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group, and any one of R21 to R28 may be the chemical formula 5, and another one may be the chemical formula 6; or the chemical formula 7.

[0175] In another embodiment of the present invention, R21 to R28 may be the same as or different from each other, and each independently is hydrogen; deuterium; the chemical formula 5; the chemical formula 6; or the chemical formula 7, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6-C20 aromatic hydrocarbon ring; or a substituted or unsubstituted C2-C20 heterocyclic ring, and any one of R21 to R28 may be the chemical formula 5, and another one may be the chemical formula 6; or the chemical formula 7.

[0176] In one embodiment of the present invention, Ar11 to Ar15 may be the same as or different from each other, and each independently is a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C2-C30 heteroaryl group.

[0177] In another embodiment of the present invention, Ar11 to Ar15 may be the same as or different from each other, and each independently may be a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group.

[0178] In another embodiment of the present invention, Ar11 and Ar12 may be the same as or different from each other, and each independently may be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrenyl group; or a substituted or unsubstituted dibenzofuranyl group.

[0179] In another embodiment of the present invention, Ar13 may be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted dibenzothiophenyl group; or a substituted or unsubstituted benzocarbazole group.

[0180] In another embodiment of the present invention, Ar14 and Ar15 may be the same as or different from each other, and each independently may be a substituted or unsubstituted phenyl group; or a substituted or unsubstituted non-phenyl group.

[0181] In one embodiment of the present invention, L11 to L16 may be the same as or different from each other, and each independently may be a direct bond; a substituted or unsubstituted C6-C30 arylene group; or a substituted or unsubstituted C2-C30 heteroarylene group.

[0182] In another embodiment of the present invention, L11 to L16 may be the same as or different from each other, and each independently may be a direct bond; a substituted or unsubstituted C6-C20 arylene group, or a substituted or unsubstituted C2-C20 heteroarylene group.

[0183] In another embodiment of the present invention, L11 and L12 may be the same as or different from each other, each independently the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted phenylene group; or a substituted or unsubstituted naphthylene group.

[0184] In another embodiment of the present invention, L13 may be a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted naphthylene group; or a substituted or unsubstituted benzocarbazolene group.

[0185] In another embodiment of the present invention, L14 to L16 may be the same as or different from each other, each independently a direct bond; or a substituted or unsubstituted phenylene group.

[0186] In one embodiment of the present invention, the heterocyclic compound represented by Chemical Formula 4 may be represented by any one of the following Chemical Formulas 4-1 to 4-4.

[0187]

Chemical Formula

[0188]

Chemical Formula

[0189] In Chemical Formulas 4-1 to 4-4, R31 to R34 are the same as or different from each other, and each independently is hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1-C60 alkyl group; substituted or unsubstituted C2-C60 alkenyl group; substituted or unsubstituted C2-C60 alkynyl group; substituted or unsubstituted C1-C60 alkoxy group; substituted or unsubstituted C3-C60 cycloalkyl group; substituted or unsubstituted C2-C60 heterocycloalkyl group; substituted or unsubstituted C6-C60 aryl group; substituted or unsubstituted C2-C60 heteroaryl group; -P(=O)R201R202; -SiR201R202R203; and -NR201R202, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6-C60 aromatic hydrocarbon ring; or a substituted or unsubstituted C2-C60 heterocycle, where R201, R202 and R203 are the same as or different from each other, and each independently is a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group, p is an integer from 0 to 3, and when p is 2 or more, R31 are the same as or different from each other, q is an integer from 0 to 3, and when q is 2 or more, R32 are the same as or different from each other, r is an integer from 0 to 4, and when r is 2 or more, R33 are the same as or different from each other, s is an integer from 0 to 2, and when s is 2 or more, R34 are the same as or different from each other, L11, L12, Ar11, Ar12, j and k are the same as the definitions in Chemical Formula 5, L13, Ar13 and l are the same as the definitions in Chemical Formula 6, L14 to L16, Ar14, Ar15, m, n and o are the same as the definitions in Chemical Formula 7.

[0190] In one embodiment of the present invention, R31 to R34 are the same as or different from each other, and each independently is hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1-C30 alkyl group; substituted or unsubstituted C2-C30 alkenyl group; substituted or unsubstituted C2-C30 alkynyl group; substituted or unsubstituted C1-C30 alkoxy group; substituted or unsubstituted C3-C30 cycloalkyl group; substituted or unsubstituted C2-C30 heterocycloalkyl group; substituted or unsubstituted C6-C30 aryl group; substituted or unsubstituted C2-C30 heteroaryl group; -P(=O)R201R202; -SiR201R202R203; or -NR201R202, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6-C30 aromatic hydrocarbon ring; or a substituted or unsubstituted C2-C30 heterocycle, and R201, R202 and R203 are the same as or different from each other, and each independently may be a substituted or unsubstituted C1-C30 alkyl group; a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C2-C30 heteroaryl group.

[0191] In another embodiment of the present invention, the R21 to R28 are the same as or different from each other, and each independently is hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1-C20 alkyl group; substituted or unsubstituted C2-C20 alkenyl group; substituted or unsubstituted C2-C20 alkynyl group; substituted or unsubstituted C1-C20 alkoxy group; substituted or unsubstituted C3-C20 cycloalkyl group; substituted or unsubstituted C2-C20 heterocycloalkyl group; substituted or unsubstituted C6-C20 aryl group; substituted or unsubstituted C2-C20 heteroaryl group; -P(=O)R201R202; -SiR201R202R203; or -NR201R202, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6-C20 aromatic hydrocarbon ring; or a substituted or unsubstituted C2-C20 heterocyclic ring, and the R201, R202 and R203 are the same as or different from each other, and each independently is a substituted or unsubstituted C1-C20 alkyl group; a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group.

[0192] In another embodiment of the present invention, the R21 to R28 are the same as or different from each other, and each independently is hydrogen; or deuterium, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6-C20 aromatic hydrocarbon ring; or a substituted or unsubstituted C2-C20 heterocyclic ring.

[0193] In one embodiment of the present invention, the R21 to R28, R31 to R34, L11 to L16 and Ar11 to Ar15 may all contain hydrogen (H) that is not deuterated.

[0194] In another embodiment of the present invention, at least one of the R21 to R28, R31 to R34, L11 to L16 and Ar11 to Ar15 contains deuterium (D), and at least one of the R21 to R28, R31 to R34, L11 to L13 and Ar11 to Ar13 may contain hydrogen that is not deuterated.

[0195] In another embodiment of the present invention, R21 to R28, R31 to R34, L11 to L16, and Ar11 to Ar15 may all contain deuterium.

[0196] In one embodiment of the present invention, the heterocyclic compound represented by Chemical Formula 4 does not contain deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be, for example, more than 0%, 1% or more, 10% or more, 20% or more, 30% or more, 40% or more, or 50% or more, and may also be 100% or less, 90% or less, 80% or less, 70% or less, or 60% or less.

[0197] In another embodiment of the present invention, the heterocyclic compound represented by Chemical Formula 4 does not contain deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be 1% to 100%.

[0198] In another embodiment of the present invention, the heterocyclic compound represented by Chemical Formula 4 does not contain deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be 20% to 90%.

[0199] In another embodiment of the present invention, the heterocyclic compound represented by Chemical Formula 4 does not contain deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be 30% to 80%.

[0200] In another embodiment of the present invention, the heterocyclic compound represented by Chemical Formula 4 does not contain deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be 50% to 70%.

[0201] When the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 4 are simultaneously included, more excellent efficiency and life effects are shown. From this, it can be expected that an exciplex phenomenon will occur when the two compounds are simultaneously included.

[0202] The exciplex phenomenon is a phenomenon in which electron exchange between two molecules releases energy of the size of the HOMO energy level of the donor (p-host) and the LUMO energy level of the acceptor (n-host). When the exciplex phenomenon occurs between two molecules, reverse intersystem crossing (RISC) occurs, whereby the internal quantum efficiency of fluorescence can be increased to 100%. When a donor (p-host) with good hole transport ability and an acceptor (n-host) with good electron transport ability are used as the host of the light-emitting layer, holes are injected into the p-host and electrons are injected into the n-host, so that the driving voltage can be lowered, which can contribute to the improvement of the lifetime. That is, when the compound represented by Chemical Formula 1 is used as the donor and the compound represented by Chemical Formula 4 is used as the acceptor, excellent device characteristics are exhibited.

[0203] In one embodiment of the present invention, when the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 4 are simultaneously included, at least one of the compounds may not contain deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may exceed 0%, be 1% or more, 10% or more, 20% or more, 30% or more, 40% or more, or 50% or more, and may be 100% or less, 90% or less, 80% or less, 70% or less, 60% or less.

[0204] In another embodiment of the present invention, at least one of the compounds may not contain deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be 1% to 100%.

[0205] In another embodiment of the present invention, at least one of the compounds may not contain deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be 20% to 90%.

[0206] In another embodiment of the present invention, at least one of the compounds may not contain deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be 30% to 80%.

[0207] In another embodiment of the present invention, at least one of the compounds may not contain deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be 50% to 70%.

[0208] In one embodiment of the present invention, the heterocyclic compound represented by Chemical Formula 4 may be represented by any one of the following compounds.

[0209]

Chemical formula

[0210]

Chemical formula

[0211]

Chemical formula

[0212]

Chemical formula

[0213]

Chemical formula

[0214]

Chemical formula

[0215]

Chem.

[0216]

Chem.

[0217]

Chem.

[0218]

Chem.

[0219]

Chem.

[0220]

Chem.

[0221]

Chem.

[0222]

Chem.

[0223] Further, one embodiment of the present invention provides a composition for an organic layer containing the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 4.

[0224] Specific details of the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 4 are as described above.

[0225] In one embodiment of the present invention, the weight ratio of the heterocyclic compound represented by Chemical Formula 1 to the heterocyclic compound represented by Chemical Formula 4 in the composition for organic layer may be, but is not limited to, 1:9 to 9:1, 1:9 to 5:5, or 2:8 to 5:5.

[0226] The composition for an organic layer can be used when forming an organic material of an organic light-emitting device, and can be preferably used in forming a host for a light-emitting layer.

[0227] In one embodiment of the present invention, the organic layer contains the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 4, and may be used in combination with a phosphorescent dopant.

[0228] The phosphorescent dopant material may be any material known in the art. For example, phosphorescent dopant materials represented by LL'MX', LL'L"M, LMX'X", L2MX', and L3M may be used, but the scope of the present invention is not limited to these examples.

[0229] The M may be iridium, platinum, osmium, or the like.

[0230] The L is sp 2 An anionic bidentate ligand coordinated to M by carbon and heteroatoms, X can function to trap electrons or holes. Non-limiting examples of L include 2-(1-naphthyl)benzoxazole, 2-phenylbenzoxazole, 2-phenylbenzothiazole, 7,8-benzoquinoline, phenylpyridine, benzothiophenylpyridine, 3-methoxy-2-phenylpyridine, thiophenylpyridine, tolylpyridine, and the like. Non-limiting examples of X' and X" include acetylacetonate (acac), hexafluoroacetylacetonate, salicylidene, picolinate, 8-hydroxyquinolinate, and the like.

[0231] Specific examples of the phosphorescent dopant are shown below, but are not limited thereto.

[0232] [Chemical formula]

[0233] In one embodiment of the present invention, the organic layer contains the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 4, and may be used in combination with an iridium-based dopant.

[0234] In one embodiment of the present invention, as the red phosphorescent dopant, (piq)2(Ir)(acac) may be used, or as the green phosphorescent dopant, Ir(ppy)3 may be used.

[0235] In one embodiment of the present invention, the content of the dopant may be 1% to 15%, preferably 2% to 10%, more preferably 3% to 7% based on the total weight of the light-emitting layer.

[0236] In one embodiment of the present invention, the organic layer may include one or more selected from the group consisting of an electron injection layer, an electron transport layer, a hole blocking layer, a light-emitting layer, a light-emitting auxiliary layer, an electron blocking layer, a hole transport layer, and a hole injection layer, and one or more layers selected from the group consisting of the electron injection layer, the electron transport layer, the hole blocking layer, the light-emitting layer, the light-emitting auxiliary layer, the electron blocking layer, the hole transport layer, and the hole injection layer may contain the heterocyclic compound represented by Chemical Formula 1.

[0237] In another embodiment of the present invention, the organic layer may include an electron injection layer or an electron transport layer, and the electron injection layer or the electron transport layer may contain the heterocyclic compound represented by Chemical Formula 1.

[0238] In another embodiment of the present invention, the organic layer may include an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer may contain the heterocyclic compound represented by Chemical Formula 1.

[0239] In another embodiment of the present invention, the organic layer may include an electron blocking layer, a light emitting layer, or a hole transporting layer, and the electron blocking layer, the light emitting layer, or the hole transporting layer may include the heterocyclic compound represented by Chemical Formula 1.

[0240] In another embodiment of the present invention, the organic layer may include a hole transporting layer, and the hole transporting layer may include the heterocyclic compound represented by Chemical Formula 1. When the heterocyclic compound represented by Chemical Formula 1 is used in the hole transporting layer, the heterocyclic compound represented by Chemical Formula 1 has a high hole mobility and an appropriate HOMO level. When the heterocyclic compound represented by Chemical Formula 1 is used as the hole transporting layer, the hole transport to the light emitting layer is easy, the driving voltage of the organic light emitting device can be reduced, and the driving efficiency and lifespan can be improved.

[0241] In another embodiment of the present invention, the organic layer may include an electron blocking layer, and the electron blocking layer may include the heterocyclic compound represented by Chemical Formula 1. Since the heterocyclic compound represented by Chemical Formula 1 has a high LUMO level, when the heterocyclic compound represented by Chemical Formula 1 is used as the electron blocking layer, the probability of holes and electrons forming an exciton can be increased, and the possibility of being emitted as light from the light emitting layer can be increased. Therefore, the electron blocking ability is improved, holes and electrons balance the charge, and the driving efficiency and lifespan of the organic light emitting device may be improved.

[0242] In another embodiment of the present invention, the organic layer may include a light emitting layer, and the light emitting layer may include the heterocyclic compound represented by Chemical Formula 1.

[0243] In another embodiment of the present invention, the organic layer includes a light emitting layer, the light emitting layer includes a host material, and the host material may include the heterocyclic compound represented by Chemical Formula 1.

[0244] In another embodiment of the present invention, the organic layer includes a light-emitting layer, and the light-emitting layer may include the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 4.

[0245] In another embodiment of the present invention, the organic layer includes a light-emitting layer, the light-emitting layer includes a host material, and the host material may include the heterocyclic compound represented by Chemical Formula 1.

[0246] In another embodiment of the present invention, the organic layer includes a light-emitting layer, the light-emitting layer may include two or more host materials, at least one of the host materials may include the heterocyclic compound represented by Chemical Formula 1, and the other one may include the heterocyclic compound represented by Chemical Formula 4.

[0247] In another embodiment of the present invention, the organic layer includes a light-emitting layer, and the light-emitting layer may use two or more host materials pre-mixed. At least one of the two or more host materials may include the heterocyclic compound represented by Chemical Formula 1, and the other one may include the heterocyclic compound represented by Chemical Formula 4.

[0248] The pre-mixed means that, in order to form the light-emitting layer, before depositing two or more host materials on the organic layer, the materials are first mixed and put into one supply source for mixing.

[0249] The organic light-emitting device according to an embodiment of the present invention may further include one layer or two 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.

[0250] In FIGS. 1 to 3, the stacking order of the electrodes and the organic layers of the organic light-emitting device according to an embodiment of the present invention is illustrated. However, the scope of the present application is not intended to be limited by these drawings, and the structures of organic light-emitting devices known in the art can also be applied to the present application.

[0251] As shown in FIG. 1, 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) is shown. However, it is not limited to such a structure, and as shown in FIG. 2, an organic light-emitting device in which a cathode (400), an organic layer (300), and an anode (200) are sequentially stacked on a substrate can also be realized.

[0252] FIG. 3 illustrates a case where the organic layer is multilayered. The organic light-emitting device according to FIG. 3 includes a hole injection layer (301), a hole transport layer (302), a light-emitting layer (303), a hole blocking layer (304), an electron transport layer (305), and an electron injection layer (306). However, the scope of the present application is not limited by such a stacked structure, and the remaining layers except the light-emitting layer may be omitted as necessary, and other necessary functional layers may be further added.

[0253] In one embodiment of the present invention, a step of preparing a substrate, a step of forming a first electrode on the substrate, a step of forming one or more organic layers on the first electrode, and a step of forming a second electrode on the one or more organic layers, a method for manufacturing an organic light-emitting device, wherein the step of forming the one or more organic layers includes a step of forming the one or more organic layers using a composition for an organic layer according to an embodiment of the present invention. Provided is a method for manufacturing an organic light-emitting device.

[0254] In one embodiment of the present invention, the step of forming the organic layer may be to pre-mix a heterocyclic compound represented by Chemical Formula 1 and a heterocyclic compound represented by Chemical Formula 4, and form the mixture using a thermal vacuum evaporation method.

[0255] The pre-mixing means that before depositing the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 4 on the organic layer, the materials are first mixed and put into one supply source for mixing.

[0256] The preliminarily mixed material can be referred to as a composition for an organic layer according to an embodiment of the present application.

[0257] The organic layer containing the heterocyclic compound represented by Chemical Formula 1 may further contain other substances as necessary.

[0258] The organic layer containing the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 4 simultaneously may further contain other substances as necessary.

[0259] In an organic light-emitting device according to an embodiment of the present invention, materials other than the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 4 are exemplified below. However, these are for illustrative purposes only and do not limit the scope of the present application, and can be replaced with materials known in the art.

[0260] As the positive electrode material, a material with a relatively large work function can be used, and a transparent conductive oxide, a metal, or a conductive polymer can be used. Specific examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof, metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), combinations of metals and oxides such as ZnO:Al or SnO2:Sb, and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

[0261] As the negative electrode material, a material with a relatively low work function can be used, such as a metal, a metal oxide, or a conductive polymer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer structured materials such as LiF / Al or LiO2 / Al, etc., but are not limited thereto.

[0262] As the hole injection layer material, known hole injection layer materials can also be used. For example, phthalocyanine compounds such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429, or starburst-type amine derivatives described in the literature [Advanced Material, 6, p.677 (1994)], such as tris(4-carbazolyl-9-ylphenyl)amine (TCTA), 4,4',4"-tris[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB), polyaniline / dodecylbenzenesulfonic acid which is a soluble conductive polymer, or poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate), polyaniline / camphor sulfonic acid, or polyaniline / poly(4-styrenesulfonate) may be used.

[0263] As the hole transport layer material, pyrazoline derivatives, arylamine-based derivatives, stilbene derivatives, triphenyldiamine derivatives, etc. may be used, and low molecular weight or high molecular weight materials may also be used.

[0264] As the electron transport layer 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 substances but also high molecular substances may be used.

[0265] As the electron injection layer material, for example, LiF is typically used in the art, but the present application is not limited thereto.

[0266] As the light-emitting layer material, red, green or blue light-emitting materials can be used, and if necessary, two or more light-emitting materials may be mixed and used. At this time, two or more light-emitting materials may be vapor-deposited and used as individual supply sources, or may be pre-mixed and vapor-deposited and used as one supply source. Further, a fluorescent material may be used as the light-emitting layer material, or a phosphorescent material may be used. As the light-emitting layer material, a material that emits light by combining holes and electrons injected from the anode and the cathode respectively alone may be used, or a material in which a host material and a dopant material are involved in light emission together may be used.

[0267] When mixing and using the host of the light-emitting layer material, hosts of the same series may be mixed and used, or hosts of different series may be mixed and used. For example, two or more materials selected from either n-type host materials or p-type host materials may be used as the host material of the light-emitting layer.

[0268] The organic light-emitting device according to an embodiment of the present invention may be a front emission type, a back emission type, or a double-sided emission type depending on the materials used.

[0269] The heterocyclic compound according to an embodiment of the present invention can also act on the same principle as that applied to the organic light-emitting device in organic electronic devices including organic solar cells, organic photoreceptors, organic transistors, etc.

Example

[0270] Examples preferred for facilitating the understanding of the present invention are shown below. However, the following examples are provided for easier understanding of the present invention and the present invention is not limited thereto.

[0271] <Production Example> Production Example 1. Production of Compound 2

Chemical formula

[0272] Production Example 1-1. Production of Compound 2-2 Compound 2-1 (15 g, 0.045 mol, 1 eq), (9-phenyl-9H-carbazol-4-yl)boronic acid (14.3 g, 0.049 mol, 1.1 eq), K2CO3 (15.6 g, 0.113 mol, 2.5 eq) and Pd(PPh3)4 (2.6 g, 0.002 mol, 0.05 eq) were placed in 1,4-dioxane (150 mL) and distilled water (30 mL), and stirred at 100 °C for 8 hours. After adding distilled water to terminate the reaction, extraction was performed using methylene chloride and water, and water was removed with MgSO4. Then, separation was carried out by a Silicagel column to obtain 16 g (yield 72%) of Compound 2-2.

[0273] Production Example 1-2. Production of Compound 2 Compound 2-2 (8 g, 0.016 mol, 1 eq), N-phenyl-[1,1'-biphenyl]-4-amine (4.2 g, 0.017 mol, 1.05 eq), NaOt-Bu (2.3 g, 0.024 mol, 1.5 eq), Pd2(dba)3 (0.7 g, 0.0008 mol, 0.05 eq) and Xphos (0.8 g, 0.0016 mol, 0.1 eq) were placed in toluene (120 mL) and stirred at 90 °C for 5 hours. After adding distilled water to terminate the reaction, extraction was carried out using methylene chloride and water, and the water was removed with MgSO4. Then, separation was performed by a Silicagel column to obtain 9 g (yield 76%) of Compound 2.

[0274] In the above Production Example 1, except that Compound A in Table 1 below was used instead of Compound 2-1, Compound B in Table 1 below was used instead of (9-phenyl-9H-carbazole-4-yl)boronic acid, N-phenyl-[1,1'-biphenyl]-4-amine, and Compound C in Table 1 below were used, the target compound was produced in the same manner as in Production Example 1 as shown in Table 1 below.

[0275]

Table 1

[0276]

Table 2

[0277]

Table 3

[0278]

Table 4

[0279]

Table 5

[0280] Production Example 2. Production of Compound 540

Chem.

[0281] Compound 2 (8 g, 0.011 mol, 1 eq), TfOH (2.7 g, 0.018 mol, 1.5 eq), and D6 - benzene (70 mL) were added, and the mixture was stirred at 80 °C for 6 hours. After adding distilled water to terminate the reaction, extraction was performed using methylene chloride and water, and the water was removed with MgSO4. Then, separation was carried out using a silica gel column to obtain 7 g (yield 83%) of Compound 540.

[0282] Production Example 3. Production of Compound NH7

Chem.

[0283] Production Example 3-1. Production of Compound NH7-2 Compound NH7 - 1 (15 g, 0.045 mol, 1 eq), phenylboronic acid (6.1 g, 0.050 mol, 1.1 eq), K2CO3 (18.8 g, 0.136 mol, 3 eq), and Pd(PPh3)4 (2.6 g, 0.002 mol, 0.05 eq) were placed in 1,4 - dioxane (150 mL) and distilled water (30 mL), and the mixture was stirred at 100 °C for 8 hours. After adding distilled water to terminate the reaction, extraction was performed using methylene chloride and water, and the water was removed with MgSO4. Then, separation was carried out using a silica gel column to obtain 12 g (yield 81%) of Compound NH7 - 2.

[0284] Production Example 3-2. Production of Compound NH7-3 Compound NH7-2 (12 g, 0.036 mol, 1 eq), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (13.7 g, 0.054 mol, 1.5 eq), KOAc (10.6 g, 0.108 mol, 3 eq), Pd2(dba)3 (1.6 g, 0.0018 mol, 0.05 eq) and XPhos (1.7 g, 0.0036 mol, 0.1 eq) were added to 1,4-dioxane (100 mL), and the mixture was stirred at 100 °C for 8 hours. After adding distilled water to terminate the reaction, extraction was carried out using methylene chloride and water, and the water was removed with MgSO4. Then, separation was performed on a silica gel column to obtain 10 g (yield 65%) of compound NH7-3.

[0285] Production Example 3-3. Production of Compound NH7 Compound NH7-3 (10 g, 0.024 mol, 1 eq), 2-chloro-4-phenyl-6-(6-phenylnaphthalen-2-yl)-1,3,5-triazine (10.3 g, 0.026 mol, 1.1 eq) and K2CO3 (9.9 g, 0.071 mol, 3 eq), Pd(PPh3)4 (1.4 g, 0.001 mol, 0.05 eq) were added to 1,4-dioxane (100 mL) and distilled water (20 mL), and the mixture was stirred at 100 °C for 6 hours. After adding distilled water to terminate the reaction, extraction was carried out using methylene chloride and water, and the water was removed with MgSO4. Then, separation was performed on a silica gel column to obtain 13 g (yield 84%) of compound NH7.

[0286] In Production Example 3, the target compound was produced in the same manner as in Production Example 3, except that Compound D in Table 2 below was used instead of Compound NH7-1, Compound E in Table 2 below was used instead of phenylboronic acid, and Compound F in Table 2 below was used instead of 2-chloro-4-phenyl-6-(6-phenylnaphthalen-2-yl)-1,3,5-triazine.

[0287]

Table 6

[0288]

Table 7

[0289] The synthesis results of the compounds described in Production Examples 1 to 3 and Tables 1 to 2 are shown in Tables 3 and 4 below.

[0290] Table 3 below is 1 the measured value of 1H NMR (CDCl3, 200 MHz), and Table 4 below is the measured value of FD-mass spectrometer (FD-MS: Field desorption mass spectrometry).

[0291]

Table 8

[0292]

Table 9

[0293]

Table 10

[0294] Experimental Example 1. Experimental Example 1-1. Fabrication of Organic Light-Emitting Device The transparent electrode ITO thin film obtained from glass for OLED (manufactured by Samsung Corning) was ultrasonically cleaned for more than 5 minutes each using trichloroethylene, acetone, ethanol, and distilled water in sequence, and then stored in isopropanol and used after that. Next, the ITO substrate was placed in the substrate folder of the vacuum evaporation apparatus. 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenyl amine (2-TNATA) was placed in the cell inside the vacuum evaporation apparatus.

[0295]

Chemical formula

[0296] After that, after evacuating until the degree of vacuum in the chamber reached 10 -6 torr, a current was applied to the cell to evaporate 2-TNATA, and a 600 Å thick hole injection layer was deposited on the ITO substrate. A compound represented by Chemical formula 1 shown in Table 5 below, a comparative example compound, or N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) was placed in another cell inside the vacuum evaporation apparatus, a current was applied to the cell to evaporate it, and a 300 Å thick hole transport layer was deposited on the hole injection layer.

[0297]

Chemical formula

[0298] After forming the hole injection layer and the hole transport layer as described above, a blue light-emitting material having the following structure was deposited thereon as a light-emitting layer. Specifically, BH1, which is a blue light-emitting host material, was vacuum-deposited with a thickness of 200 Å in one cell inside the vacuum evaporation apparatus, and then D1, which is a blue light-emitting dopant material, was vacuum-deposited at 5% with respect to the host material. After that, E1 was deposited with a thickness of 300 Å as an electron transport layer.

[0299]

Chem.

[0300] Thereafter, lithium fluoride (LiF) was deposited to a thickness of 10 Å as an electron injection layer, and Al was deposited to a thickness of 1000 Å to form a cathode, thereby fabricating an organic light-emitting device.

[0301] On the other hand, all the organic compounds necessary for fabricating the organic light-emitting device were vacuum sublimation purified at 10 -6 ~10 -8 torr and used for fabricating the organic light-emitting device.

[0302] Experimental Example 1-2. Driving Voltage and Luminescence Efficiency of Organic Light-Emitting Device Regarding the organic electroluminescent device fabricated as described above, the electroluminescence (EL) characteristics were measured using Mcscience's M7000, and the lifetime T, which is the time when the luminance reaches 95% of the initial luminance when the reference luminance is 700 cd / m 2 , was measured through the lifetime measurement device (M6000) manufactured by Mcscience with the measurement results. 95

[0303] The driving voltage, luminous efficiency, and lifetime (T 95 ) of the blue organic light-emitting device fabricated by the above manufacturing method were measured, and the results are as shown in Table 5.

[0304]

Table 11

[0305] [Compound of Comparative Example]

Chem.

[0306] From the results in Table 5 above, the blue organic light-emitting devices of Examples 1 to 27 using the heterocyclic compound represented by Chemical Formula 1 of the present invention as the hole transport layer had a lower driving voltage, and significantly better luminous efficiency and lifespan compared to Comparative Examples 1 to 6. Specifically, the heterocyclic compound represented by Chemical Formula 1 of the present invention can suppress the π-π stacking of aromatic rings and prevent the phenomenon of deterioration of the characteristics of the organic light-emitting device. Therefore, an organic light-emitting device using the heterocyclic compound represented by Chemical Formula 1 of the present invention as the hole transport layer can achieve low driving voltage, high luminous efficiency, and high lifespan characteristics.

[0307] The H1 compound of Comparative Example 2 does not contain an arylamine group corresponding to Chemical Formula 2, but contains a triazine group instead of the arylamine group. The H2 compound of Comparative Example 3 has a core structure different from that of the heterocyclic compound represented by Chemical Formula 1 of the present invention. The H3 compound of Comparative Example 4 contains two carbazole groups corresponding to Chemical Formula 3. The H4 compound of Comparative Example 5 has an Ar2 or Ar3 of the arylamine group corresponding to Chemical Formula 2 containing a heteroaryl group. The H5 compound of Comparative Example 6 has a carbazole group corresponding to Chemical Formula 3 linked by a phenylene linker.

[0308] NPB used as a compound for the conventional hole transport layer and the compounds of Comparative Examples 2 to 6 have a core structure or substituents different from those of the heterocyclic compound represented by Chemical Formula 1 of the present invention, and thus showed a higher driving voltage, lower luminous efficiency, and shorter lifespan than the present invention.

[0309] From the above results, it can be seen that an organic light-emitting device containing the heterocyclic compound represented by Chemical Formula 1 of the present invention as the hole transport layer exhibits low driving voltage, high luminous efficiency, and high lifespan characteristics.

[0310] Experimental Example 2. Experimental Example 2-1. Fabrication of Organic Light-Emitting Device The transparent electrode ITO thin film obtained from glass for OLED (manufactured by Samsung Corning) was ultrasonically cleaned for more than 5 minutes each using trichloroethylene, acetone, ethanol, and distilled water in sequence, then stored in isopropanol and used after that. The ITO substrate was placed in the substrate folder of the vacuum evaporation apparatus, and 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenyl amine (2-TNATA) was put in.

[0311]

Chemical formula

[0312] After that, after evacuating until the degree of vacuum in the chamber reached 10 -6 torr, a current was applied to the cell to evaporate 2-TNATA, and a 600 Å-thick hole injection layer was deposited on the ITO substrate. N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) was put in another cell in the vacuum evaporation apparatus, a current was applied to the cell to evaporate it, and a 250 Å-thick hole transport layer was deposited on the hole injection layer.

[0313]

Chemical formula

[0314] Next, as an electron blocking layer, the compound represented by Chemical formula 1 shown in Table 6 or the comparative example compound was deposited with a thickness of 50 Å. On top of that, a blue light-emitting material with the following structure was deposited as a light-emitting layer. Specifically, BH1, which is a blue light-emitting host material, was vacuum-deposited with a thickness of 200 Å in one cell in the vacuum evaporation apparatus, and on top of that, D1, which is a blue light-emitting dopant material, was vacuum-deposited at 5% with respect to the host material.

[0315] [Chemical formula]

[0316] Thereafter, a compound of the following structural formula E1 was deposited as an electron transport layer with a thickness of 300 Å.

[0317] [Chemical formula]

[0318] Thereafter, lithium fluoride (LiF) was deposited as an electron injection layer with a thickness of 10 Å, and Al was deposited with a thickness of 1000 Å to form a cathode, thereby fabricating an organic light-emitting device.

[0319] On the other hand, all the organic compounds required for the fabrication of the organic light-emitting device were vacuum sublimation purified under 10 -6 ~10 -6 torr and used for the fabrication of the organic light-emitting device.

[0320] Experimental Example 2-2. Driving Voltage and Luminescence Efficiency of Organic Light-Emitting Device Regarding the organic electroluminescent device fabricated as described above, the electroluminescence (EL) characteristics were measured with an Mcscience M7000, and based on the measurement results, the lifetime T 2 , which is the time when the initial luminance becomes 95% with respect to the reference luminance of 700 cd / m 95 , was measured through a lifetime measurement device (M6000) manufactured by Mcscience.

[0321] The measured results of the driving voltage, luminous efficiency, and lifetime (T 95 ) of the blue organic light-emitting device fabricated by the above manufacturing method are as shown in Table 6.

[0322] [Table 12]

[0323] [Comparative Example Compound] [Chemical formula]

[0324] From the results in Table 6 above, the blue organic light-emitting devices of Examples 28 to 54 using the heterocyclic compound represented by Chemical Formula 1 of the present invention as an electron blocking layer had a lower driving voltage, significantly better luminous efficiency and lifespan compared to Comparative Examples 7 to 11. In the case of electrons, when they pass through the hole transport layer without being combined in the light-emitting layer and reach the anode, a phenomenon occurs where the efficiency and lifespan of the organic light-emitting device decrease. When a compound having a high LUMO level is used as the electron blocking layer, electrons trying to reach the anode after passing through the light-emitting layer are blocked by the energy barrier of the electron blocking layer, and the above phenomenon can be prevented. That is, the probability of holes and electrons forming an exciton increases, and the possibility of being emitted as light from the light-emitting layer increases. Since the heterocyclic compound represented by Chemical Formula 1 of the present invention is a compound having a high LUMO level, the above phenomenon can be prevented. Therefore, an organic light-emitting device using the heterocyclic compound represented by Chemical Formula 1 of the present invention as an electron blocking layer can obtain low driving voltage, high luminous efficiency and high lifespan characteristics.

[0325] As described above in Experimental Example 1, Comparative Example Compounds H1 to H5 have a core structure or substituents different from those of the heterocyclic compound represented by Chemical Formula 1 of the present invention. Therefore, they showed a lower LUMO level than the heterocyclic compound represented by Chemical Formula 1 of the present invention, and had a higher driving voltage, lower luminous efficiency and shorter lifespan than the present invention.

[0326] From the above results, it can be seen that an organic light-emitting device containing the heterocyclic compound represented by Chemical Formula 1 of the present invention as an electron blocking layer exhibits low driving voltage, high luminous efficiency and high lifespan characteristics.

[0327] Experimental Example 3. Experimental Example 3-1. Fabrication of Organic Light-Emitting Device A glass substrate coated with a 1,500 Å-thick ITO thin film was cleaned with ultrasonic distilled water. After the distilled water cleaning was completed, ultrasonic cleaning was performed with solvents such as acetone, methanol, and isopropyl alcohol and then dried. After that, UVO (Ultraviolet Ozone) treatment was carried out using UV in a UV cleaner for 5 minutes. Then, the substrate was transferred to a plasma cleaner (PT), and plasma treatment was performed in a vacuum state for ITO work function and residual film removal, and then transferred to a thermal evaporation apparatus for organic vapor deposition.

[0328] On the ITO transparent electrode (positive electrode), 4,4',4''-tris[2-naphthyl(phenyl)amino]triphenylamine (4,4'',4''-Tris[2-naphthyl(phenyl)amino]triphenylamine), 2-TNATA) was formed as a hole injection layer which is a common layer, N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) was formed as a hole transport layer, and cyclohexylidenebis[N,N-bis(4-methylphenyl)benzenamine] (TAPC) was formed as an electron blocking layer.

[0329] [Chemical formula]

[0330] On it, the light-emitting layer was thermally vacuum-deposited as follows. For the light-emitting layer, two compounds described in Table 7 below were deposited from one source as a red host, (piq)2(Ir)(acac) was used as a red phosphorescent dopant, and the host was doped with 3 wt% of the Ir compound and deposited to a thickness of 400 Å. Thereafter, Bphen was deposited to a thickness of 30 Å as a hole-blocking layer, and TPBI was deposited thereon to a thickness of 250 Å as an electron-transporting layer. Finally, lithium fluoride (LiF) was deposited to a thickness of 10 Å on the electron-transporting layer to form an electron-injecting layer, and then aluminum (Al) was deposited to a thickness of 1,200 Å on the electron-injecting layer to form a negative electrode, thereby manufacturing an organic electroluminescent device.

[0331]

Chem.

[0332] On the other hand, all the organic compounds required for fabricating the OLED device were purified by vacuum sublimation at 10 -6 ~10 -6 torr for each material and used for fabricating the OLED (Organic Light Emitting Device).

[0333] Experimental Example 3-2. Driving Voltage and Luminescence Efficiency of Organic Light-Emitting Device Regarding the organic electroluminescent device fabricated as described above, the electroluminescence (EL) characteristics were measured using M7000 of Mcscience Co., Ltd., and through the lifetime measuring device (M6000) manufactured by Mcscience Co., Ltd. with the measurement results, when the reference luminance was 6,000 cd / m 2 T 90 was measured. The measurement results of the driving voltage, luminous efficiency, color coordinates (CIE), and lifetime of the organic light-emitting device manufactured according to the present invention are shown in Table 7 below. The T 90 means the lifetime (unit: hour) which is the time to reach 90% of the initial luminance.

[0334]

Table 13

[0335]

Table 14

[0336] [Comparative Example Compounds] [Chemical Formula]

[0337] From the results in Table 7 above, in Examples 55 to 85 of the red organic light-emitting devices in which the heterocyclic compound represented by Chemical Formula 1 of the present invention was used as a P-type host and the heterocyclic compound represented by Chemical Formula 4 was used as an N-type host in the light-emitting layer, and these were mixed and used as the light-emitting layer, the driving voltage was lower and the luminous efficiency and lifetime were significantly superior compared to Comparative Examples 12 to 16.

[0338] When a donor (p-host) with good hole transport ability and an acceptor (n-host) with good electron transport ability are used as the host of the light-emitting layer, due to the exciplex phenomenon of the two compounds, holes are injected into the p-host and electrons are injected into the n-host, so the charge balance in the device can be adjusted. Therefore, it was found that when an N-type host compound having appropriate electron transfer characteristics and a P-type host compound having appropriate hole transfer characteristics are combined at an appropriate ratio, it is helpful for improving the driving efficiency and lifetime.

[0339] As described above in Experimental Example 1, Comparative Example Compounds H1 to H5 have a core structure or substituents different from those of the heterocyclic compound represented by Chemical Formula 1 of the present invention. Therefore, they showed lower hole transport ability than the heterocyclic compound represented by Chemical Formula 1 of the present invention, had a higher driving voltage than the present invention, and showed lower luminous efficiency and lifetime.

[0340] From the above results, it can be seen that the organic light-emitting device containing the heterocyclic compound represented by Chemical Formula 1 of the present invention and the heterocyclic compound represented by Chemical Formula 4 in the light-emitting layer simultaneously exhibits low driving voltage, high luminous efficiency and high lifetime characteristics. [Explanation of Reference Numerals]

[0341] 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, The R1 to R10 are the same or different and each independently represents hydrogen; deuterium; a halogen; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; Ar1; -P(=O)R101R102; -SiR101R10 2R103; and the following chemical formula 2, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6-C60 aromatic hydrocarbon ring; or a substituted or unsubstituted C2-C60 heterocycle, wherein R101, R102, and R103 are the same or different, and each independently represents a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group; Any one of R1 to R10 is represented by the following formula 2, and the other is Ar1, The Ar1 is a substituted or unsubstituted C6 to C60 aryl group; or the following chemical formula 3: 【Chemistry 2】 In the above Chemical Formula 2, wherein L1 to L3 are the same or different and each independently represents a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group; wherein a is an integer of 0 to 5, and when a is 2 or more, L1 are the same or different; The b is an integer of 0 to 5, and when b is 2 or more, L2 are the same or different; wherein c is an integer of 0 to 5, and when c is 2 or more, L3 are the same or different; The Ar2 and Ar3 are the same or different, and each independently represents a substituted or unsubstituted C6 to C60 aryl group; or the following chemical formula 3: Any one of Ar1 to Ar3 is represented by the following chemical formula 3: 【Chemistry 3】 In the above Chemical Formula 3, R11 and R12 are the same or different and each independently represent hydrogen; deuterium; a halogen; a cyano group; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C2-C60 alkenyl group; a substituted or unsubstituted C2-C60 alkynyl group; a substituted or unsubstituted C1-C60 alkoxy group; a substituted or unsubstituted C3-C60 cycloalkyl group; a substituted or unsubstituted C2-C60 heterocycloalkyl group; a substituted or unsubstituted C6-C60 aryl group; a substituted or unsubstituted C2-C60 heteroaryl group; -P (=O) selected from the group consisting of R101R102; -SiR101R102R103; and -NR101R102, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same or different from each other and each independently represent a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; The d is an integer of 0 to 3, and when the d is 2 or more, R11 are the same or different from each other, The e is an integer of 0 to 4, and when the e is 2 or more, R12 are the same or different, The Ar4 is a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

2. The heterocyclic compound represented by the chemical formula 1 is the heterocyclic compound according to claim 1, characterized in that it is represented by any one of the following chemical formulas 1-1 to 1-3: 【Chemistry 4】 【Chemistry 5】 【Chemistry 6】 In the above Chemical Formulas 1-1 to 1-3, The R13 to R16 are the same or different and each independently represent hydrogen; deuterium; a halogen; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P( =O) selected from the group consisting of R101R102; -SiR101R102R103; and -NR101R102, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102 and R103 are the same or different and each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; wherein f is an integer of 0 to 5, and when f is 2 or more, R13 are the same or different from each other; The g is an integer of 0 to 3, and when the g is 2 or more, R14 are the same or different from each other, The h is an integer of 0 to 6, and when the h is 2 or more, R15 are the same or different from each other. The i is an integer of 0 to 2, and when the i is 2 or more, R16 are the same or different, Ar1 is defined as in Formula 1; The L1 to L3, Ar2, Ar3 and a to c are defined as in the above Chemical Formula 2.

3. The heterocyclic compound according to claim 1, wherein Ar4 is a substituted or unsubstituted C6 to C60 aryl group.

4. The heterocyclic compound according to claim 1, wherein L1 to L3 are the same or different and each independently represents a direct bond; or a substituted or unsubstituted C6 to C60 arylene group.

5. The heterocyclic compound according to claim 1, wherein the heterocyclic compound represented by Chemical Formula 1 does not contain deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms is 1% to 100%.

6. The heterocyclic compound represented by the chemical formula 1 is the heterocyclic compound according to claim 1, which is represented by any one of the following compounds: 【Chemistry 7】 【Chemistry 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 【Chemistry 18】 【Chemistry 19】 【Chemistry 20】 【Chemistry 21】 【Chemical 22】 【Chemistry 23】 【Chemistry 24】 【Chemistry 25】 【Chemistry 26】 【Chemical 27】 【Chemistry 28】 【Chemical 29】 【Chemistry 30】 【Chemistry 31】 【Chemistry 32】 【Chemical 33】

7. first electrode, a second electrode provided opposite the first electrode; and An organic light emitting device including one or more organic layers provided between the first electrode and the second electrode, 7. An organic light-emitting device, wherein at least one of the organic layers contains the heterocyclic compound according to claim 1.

8. The organic layer includes a hole transport layer, The organic light-emitting device according to claim 7 , wherein the hole transport layer contains the heterocyclic compound.

9. The organic layer includes an electron blocking layer, The organic light-emitting device according to claim 7 , wherein the electron blocking layer comprises the heterocyclic compound.

10. the organic layer includes a light-emitting layer, The organic light-emitting device according to claim 7 , wherein the light-emitting layer contains the heterocyclic compound.

11. the organic layer includes a light-emitting layer, The light-emitting layer comprises a host material, The organic light emitting device according to claim 7 , wherein the host material comprises the heterocyclic compound.

12. The organic light emitting device according to claim 7 , wherein the organic layer further comprises a heterocyclic compound represented by the following Chemical Formula 4: 【Chemical 34】 In the above Chemical Formula 4, R21 to R28 are the same or different and each independently represent hydrogen; deuterium; a halogen; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; -P(=O)R201R202; -SiR201R202R203; or selected from the group consisting of the following chemical formula 5; the following chemical formula 6; and the following chemical formula 7; or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C60 heterocycle, wherein R201, R202, and R203 are the same or different, and each independently represents a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; Any one of R21 to R28 is represented by the following formula 5, and the other is represented by the following formula 6; or the following formula 7: 【Chemistry 35】 In the above Chemical Formulas 5 to 7, wherein L11 to L16 are the same or different and each independently represents a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group; wherein j is an integer of 0 to 5, and when j is 2 or more, L11 are the same or different; wherein k is an integer of 0 to 5, and when k is 2 or more, L12 are the same or different; wherein l is an integer of 0 to 5, and when l is 2 or more, L13 are the same or different; wherein m is an integer of 0 to 5, and when m is 2 or more, L14 are the same or different; wherein n is an integer of 0 to 5, and when n is 2 or more, L15 are the same or different; wherein o is an integer of 0 to 5, and when o is 2 or more, L16 are the same or different; The Ar11 to Ar15 are the same or different and each independently represents a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

13. The organic light-emitting device according to claim 12, wherein the heterocyclic compound represented by Chemical Formula 4 is represented by any one of the following Chemical Formulas 4-1 to 4-4: 【Chemical 36】 【Chemical 37】 【Chemical Formula 38】 【Chemical Formula 39】 In the above Chemical Formulas 4-1 to 4-4, The R31 to R34 are the same or different and each independently represent hydrogen; deuterium; a halogen; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P( =O) selected from the group consisting of R201R202; -SiR201R202R203; and -NR201R202, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6-C60 aromatic hydrocarbon ring; or a substituted or unsubstituted C2-C60 heterocycle, wherein R201, R202 and R203 are the same or different and each independently a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group; The p is an integer of 0 to 3, and when the p is 2 or more, R31 are the same or different from each other, The q is an integer of 0 to 3, and when the q is 2 or more, R32 are the same or different, The r is an integer of 0 to 4, and when the r is 2 or more, R33 are the same or different from each other, The s is an integer of 0 to 2, and when the s is 2 or more, R34 are the same or different from each other, L11, L12, Ar11, Ar12, j and k are defined as in Formula 5; L13, Ar13 and l are defined as in Formula 6; The L14 to L16, Ar14, Ar15, m, n and o are defined as in the above Chemical Formula 7.

14. The organic light-emitting device according to claim 12, wherein the heterocyclic compound represented by Chemical Formula 4 does not contain deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms is 1% to 100%.

15. The organic light-emitting device according to claim 12, wherein the heterocyclic compound represented by Chemical Formula 4 is represented by any one of the following compounds: 【Chemistry 40】 【Chemistry 41】 【Chemistry 42】 【Chemistry 43】 【Chemistry 44】 【Chemistry 45】 【Chemistry 46】 【Chemistry 47】 【Chemistry 48】 【Chemistry 49】 【Chemistry 50】 【Chemistry 51】 【Chemistry 52】 【Chemistry 53】

16. 8. The organic light-emitting device according to claim 7, further comprising one or more layers selected from the group consisting of an emitting layer, an emitting auxiliary 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.

17. A composition for an organic layer comprising the heterocyclic compound represented by Chemical Formula 1 according to claim 1 and a heterocyclic compound represented by Chemical Formula 4: 【Chemical 54】 In the above Chemical Formula 4, R21 to R28 are the same or different and each independently represent hydrogen; deuterium; a halogen; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; -P(=O)R201R202; -SiR201R202R203; or selected from the group consisting of the following chemical formula 5; the following chemical formula 6; and the following chemical formula 7; or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C60 heterocycle, wherein R201, R202, and R203 are the same or different, and each independently represents a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; Any one of R21 to R28 is represented by the following formula 5, and the other is represented by the following formula 6; or the following formula 7: 【Chemistry 55】 In the above Chemical Formulas 5 to 7, wherein L11 to L16 are the same or different and each independently represents a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group; wherein j is an integer of 0 to 5, and when j is 2 or more, L11 are the same or different; wherein k is an integer of 0 to 5, and when k is 2 or more, L12 are the same or different; wherein l is an integer of 0 to 5, and when l is 2 or more, L13 are the same or different; wherein m is an integer of 0 to 5, and when m is 2 or more, L14 are the same or different; wherein n is an integer of 0 to 5, and when n is 2 or more, L15 are the same or different; wherein o is an integer of 0 to 5, and when o is 2 or more, L16 are the same or different; The Ar11 to Ar15 are the same or different and each independently represents a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

18. The composition for organic layer according to claim 17, wherein the weight ratio of the heterocyclic compound represented by Chemical Formula 1 to the heterocyclic compound represented by Chemical Formula 4 is 1:9 to 9:1.

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