KR102799966B1 - Heterocyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

The present specification relates to a heterocyclic compound of chemical formula 1 and an organic light-emitting device comprising the same.

Description

Heterocyclic compound and organic light emitting device comprising the same {HETEROCYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME}

The present specification relates to a heterocyclic compound and an organic light-emitting device comprising the same.

In general, the organic luminescence phenomenon refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic light-emitting devices utilizing the organic luminescence phenomenon usually have a structure including an anode, a cathode, and an organic layer therebetween. Here, the organic layer is often composed of a multilayer structure composed of different materials in order to increase the efficiency and stability of the organic light-emitting device, and can be composed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In the structure of such an organic light-emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons are injected from the cathode into the organic layer, and when the injected holes and electrons meet, excitons are formed, and when these excitons fall back to the ground state, light is emitted.

There is a continued need for the development of new materials for organic light-emitting devices such as the above.

United States Patent Application Publication No. 2004-0251816

The present specification provides a heterocyclic compound and an organic light-emitting device comprising the same.

One embodiment of the present specification provides a heterocyclic compound represented by the following chemical formula 1.

[Chemical Formula 1]

In the above chemical formula 1,

L1 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group,

Ar1 is a heterocyclic group substituted or unsubstituted with one or more groups selected from the group consisting of aryl groups and heterocyclic groups,

When the substituted or unsubstituted divalent heterocyclic group of the above L1 is a substituted or unsubstituted divalent carbazole group, the substituted or unsubstituted divalent carbazole group is represented by the following chemical formula 2,

[Chemical formula 2]

In the above chemical formula 2,

Any one of R1 to R8 is of the chemical formula 1. is a part that is bonded to, and among R1 to R8, the chemical formula 1 The remaining portion that is not bonded to, and one of Ar2 is a portion that is bonded to Ar1 of the chemical formula 1,

Among the above R1 to R8 and Ar2, the chemical formula 1 Or the remaining moieties not bonded to Ar1 are the same or different, and each independently is hydrogen; an aryl group or a heterocyclic group.

In addition, one embodiment of the present specification provides an organic light-emitting device including a first electrode; a second electrode provided opposite the first electrode; and at least one organic layer provided between the first electrode and the second electrode, wherein at least one of the organic layers includes the heterocyclic compound.

A heterocyclic compound according to one embodiment of the present specification can be used as a material of an organic layer of an organic light-emitting device. A heterocyclic compound according to another embodiment can improve efficiency, low driving voltage, and/or lifespan characteristics in an organic light-emitting device.

Figures 1 and 2 illustrate examples of organic light-emitting devices according to one embodiment of the present specification.

Hereinafter, the present specification will be described in more detail.

One embodiment of the present specification provides a heterocyclic compound represented by the chemical formula 1.

Throughout this specification, the term "combination of these" included in the expressions in the Makushi format means a mixture or combination of one or more selected from the group consisting of the components described in the Makushi format, and means including one or more selected from the group consisting of said components.

Examples of substituents in this specification are described below, but are not limited thereto.

In this specification, means the connecting part.

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

The term "substituted or unsubstituted" as used herein means substituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a cyano group; an alkyl group; a cycloalkyl group; an alkoxy group; an aryloxy group; an alkylthioxy group; an arylthioxy group; an alkenyl group; a haloalkyl group; a haloalkoxy group; an arylalkyl group; a silyl group; a boron group; an amine group; an aryl group; and a heterocyclic group, or has no substituents.

In this specification, examples of halogen groups include fluorine, chlorine, bromine or iodine.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, These include, but are not limited to, 2-methylpentyl, 4-methylhexyl, and 5-methylhexyl.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably one having 3 to 30 carbon atoms, and specifically includes, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, an adamantyl group, a bicyclo[2.2.1]octyl group, a norbornyl group, and the like.

In the present specification, the alkoxy group may be linear, branched or cyclic. The carbon number of the alkoxy group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, the alkoxy group may be, but is not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, and the like.

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples include, but are not limited to, vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl, and styrenyl.

In this specification, the haloalkyl group means that at least one halogen group is substituted for hydrogen in the alkyl group among the definitions of the alkyl group.

In this specification, the haloalkoxy group means a group in which at least one halogen group is substituted for hydrogen in the alkoxy group as defined above.

In the present specification, the aryl group is not particularly limited, but is preferably one having 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.

When the above aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30 carbon atoms. Specifically, the monocyclic aryl group may include, but is not limited to, a phenyl group, a biphenyl group, a terphenyl group, etc.

When the above aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. However, it is preferable that the number of carbon atoms is 10 to 30. Specifically, the polycyclic aryl group may include, but is not limited to, a naphthyl group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a phenalene group, a perylene group, a chrysene group, a fluorene group, etc.

In the present specification, the fluorene group may be substituted, and adjacent groups may be combined with each other to form a ring.

When the above fluorene group is substituted, , , , , , , and These include, but are not limited to:

In this specification, the term "adjacent" may refer to a substituent substituted on an atom directly connected to the atom substituted by the substituent, a substituent stereostructurally closest to the substituent, or another substituent substituted on the atom substituted by the substituent. For example, two substituents substituted at the ortho position in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring may be interpreted as "adjacent" groups to each other.

In this specification, an arylalkyl group means that the alkyl group is substituted with an aryl group, and the aryl group and alkyl group of the arylalkyl group may be applied with the examples of the aryl group and alkyl group described above.

In this specification, the aryloxy group means an alkoxy group in which an alkyl group is substituted with an aryl group in the definition of the alkoxy group, and examples of the aryloxy group include, but are not limited to, a phenoxy group, a p-tolyloxy group, a m-tolyloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6-trimethylphenoxy group, a p-tert-butylphenoxy group, a 3-biphenyloxy group, a 4-biphenyloxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 4-methyl-1-naphthyloxy group, a 5-methyl-2-naphthyloxy group, a 1-anthryloxy group, a 2-anthryloxy group, a 9-anthryloxy group, a 1-phenanthryloxy group, a 3-phenanthryloxy group, and a 9-phenanthryloxy group.

In this specification, the alkyl group of the alkylthioxy group is the same as the examples of the alkyl group described above. Specifically, the alkylthioxy group includes, but is not limited to, a methylthioxy group, an ethylthioxy group, a tert-butylthioxy group, a hexylthioxy group, an octylthioxy group, etc.

In this specification, the aryl group in the arylthioxy group is the same as the examples of the aryl group described above. Specifically, the arylthioxy group includes, but is not limited to, a phenylthioxy group, a 2-methylphenylthioxy group, a 4-tert-butylphenylthioxy group, etc.

In the present specification, a heterocyclic group includes one or more non-carbon atoms or heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S, and includes an aromatic heterocyclic group or an aliphatic heterocyclic group. The aromatic heterocyclic group may be represented by a heteroaryl group. The number of carbon atoms in the heterocyclic group is not particularly limited, but is preferably 2 to 30 carbon atoms, and the heterocyclic group may be monocyclic or polycyclic. Examples of heterocyclic groups include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, pyridine group, bipyridine group, pyrimidine group, triazine group, triazole group, acridine group, pyridazine group, pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, pyrido pyrimidine group, pyrido pyrazine group, pyrazino pyrazine group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuran group, phenanthridine, phenanthroline, isoxazole group, thiadiazole group, Examples thereof include, but are not limited to, a dibenzofuran group, a dibenzosilole group, a phenoxathiine group, a phenoxazine group, a phenothiazine group, a dihydroindenocarbazole group, a spirofluorenxanthene group, a spirofluorenethioxanthene group, a tetrahydronaphthothiophene group, a tetrahydronaphthofuran group, a tetrahydrobenzothiophene group, and a tetrahydrobenzofuran group.

In the present specification, the silyl group may be an alkylsilyl group, an arylsilyl group, an alkylarylsilyl group, a heteroarylsilyl group, etc. The alkyl group among the alkylsilyl groups may be applied with the examples of the above-described alkyl group, the aryl group among the arylsilyl groups may be applied with the examples of the above-described aryl group, the alkyl group and aryl group among the alkylarylsilyl groups may be applied with the examples of the above-described alkyl group and aryl group, and the heteroaryl group among the heteroarylsilyl groups may be applied with the examples of the above-described heterocyclic group.

In the present specification, the boron group may be -BR ₁₀₀ R ₁₀₁ , wherein R ₁₀₀ and R ₁₀₁ are the same or different, and each independently selected from the group consisting of hydrogen; deuterium; halogen; a nitrile group; a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms. The boron group specifically includes, but is not limited to, a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, a phenyl boron group, etc.

In the present specification, the amine group can be selected from the group consisting of -NH ₂ , an alkylamine group, an N-alkylarylamine group, an arylamine group, an N-arylheteroarylamine group, an N-alkylheteroarylamine group, and a heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, anthracenylamine group, a 9-methyl-anthracenylamine group, a diphenylamine group, a ditolylamine group, an N-phenyltolylamine group, a triphenylamine group, an N-phenylbiphenylamine group, an N-phenylnaphthylamine group, an N-biphenylnaphthylamine group; Examples thereof include, but are not limited to, N-naphthylfluorenylamine group, N-phenylphenanthrenylamine group, N-biphenylphenanthrenylamine group, N-phenylfluorenylamine group, N-phenylterphenylamine group, N-phenanthrenylfluorenylamine group, N-biphenylfluorenylamine group, etc.

In this specification, an N-alkylarylamine group means an amine group in which an alkyl group and an aryl group are substituted for N of the amine group. The alkyl group and aryl group in the N-alkylarylamine group are the same as the examples of the alkyl group and aryl group described above.

In this specification, the N-arylheteroarylamine group means an amine group in which an aryl group and a heteroaryl group are substituted on N of the amine group. The aryl group and heteroaryl group in the N-arylheteroarylamine group are the same as the examples of the aryl group and heterocyclic group described above.

In this specification, an N-alkylheteroarylamine group means an amine group in which an alkyl group and a heteroaryl group are substituted for N of the amine group. The alkyl group and heteroaryl group in the N-alkylheteroarylamine group are the same as the examples of the alkyl group and heterocyclic group described above.

In the present specification, examples of the alkylamine group include a substituted or unsubstituted monoalkylamine group, or a substituted or unsubstituted dialkylamine group. The alkyl group in the alkylamine group may be a linear or branched alkyl group. The alkylamine group including two or more alkyl groups may include a linear alkyl group, a branched alkyl group, or a linear alkyl group and a branched alkyl group at the same time. For example, the alkyl group in the alkylamine group may be selected from the examples of the above-mentioned alkyl groups.

In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, or a substituted or unsubstituted diheteroarylamine group. The heteroarylamine group including two or more heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or both a monocyclic heteroaryl group and a polycyclic heteroaryl group. For example, the heteroaryl group in the heteroarylamine group may be selected from the examples of the above-mentioned heterocyclic group.

In the present specification, the alkyl group among the N-alkylarylamine group, the alkylthioxy group, and the N-alkylheteroarylamine group is the same as the examples of the alkyl group described above. Specifically, the alkylthioxy group includes, but is not limited to, a methylthioxy group, an ethylthioxy group, a tert-butylthioxy group, a hexylthioxy group, and an octylthioxy group.

In this specification, the aryl group among the aryloxy group, the arylthioxy group, the N-arylalkylamine group, and the N-arylheteroarylamine group is the same as the examples of the aryl group described above. Specifically, examples of the aryloxy group include, but are not limited to, a phenoxy group, a p-toryloxy group, a m-toryloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6-trimethylphenoxy group, a p-tert-butylphenoxy group, a 3-biphenyloxy group, a 4-biphenyloxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 4-methyl-1-naphthyloxy group, a 5-methyl-2-naphthyloxy group, a 1-anthryloxy group, a 2-anthryloxy group, a 9-anthryloxy group, a 1-phenanthryloxy group, a 3-phenanthryloxy group, and a 9-phenanthryloxy group, and examples of the arylthioxy group include, but are not limited to, a phenylthioxy group, a 2-methylphenylthioxy group, and a 4-tert-butylphenylthioxy group.

In this specification, an arylene group means a divalent group having two bonding positions to an aryl group. The description of the aryl group described above can be applied to each of these, except that they are each divalent.

In this specification, a divalent heterocyclic group means a heterocyclic group having two bonding positions, i.e. a divalent group. The description of the heterocyclic group described above can be applied to each of these groups, except that they are each divalent.

In this specification, the "bonding site" means a site where a specific substituent is directly bonded to another substituent. For example, in the chemical formulas 1 and 2, when Ar2 of the chemical formula 2 is a "bonding site" to Ar1 of the chemical formula 1, Ar2 is directly bonded to Ar1.

According to one embodiment of the present specification, L1 is a direct bond; a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted divalent monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

According to one embodiment of the specification, the L1 is a direct bond; a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted divalent monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms.

According to one embodiment of the present specification, when the substituted or unsubstituted divalent heterocyclic group of L1 is a substituted or unsubstituted divalent carbazole group, the substituted or unsubstituted divalent carbazole group is represented by the chemical formula 2.

According to one embodiment of the present specification, L1 is a direct bond; an arylene group; or a divalent heterocycle.

According to one embodiment of the present specification, L1 is a direct bond; a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; or a divalent monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms.

According to one embodiment of the specification, the L1 is a direct bond; a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms; or a divalent monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms.

According to one embodiment of the present specification, when the divalent C2 to C20 monocyclic or polycyclic heterocyclic group of L1 is a divalent carbazole group, the divalent carbazole group is represented by the chemical formula 2.

According to one embodiment of the present specification, L1 is a direct bond; a phenylene group; a naphthylene group; a divalent dibenzofuran group.

According to one embodiment of the present specification, Ar1 is a heterocyclic group unsubstituted or substituted with one or more selected from the group consisting of an unsubstituted aryl group and an unsubstituted heterocyclic group.

According to one embodiment of the present specification, Ar1 is a heterocyclic group substituted with one or more atoms selected from the group consisting of an unsubstituted aryl group and an unsubstituted heterocyclic group.

According to one embodiment of the present specification, Ar1 is an unsubstituted heterocyclic group.

According to one embodiment of the present specification, Ar1 is a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, unsubstituted or substituted with one or more selected from the group consisting of a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

According to one embodiment of the present specification, Ar1 is a monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms, which is unsubstituted or substituted with one or more selected from the group consisting of a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, and a monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms.

According to one embodiment of the present specification, Ar1 is a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms, unsubstituted or substituted with one or more selected from the group consisting of an unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and an unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

According to one embodiment of the present specification, Ar1 is a monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms, which is unsubstituted or substituted with one or more selected from the group consisting of an unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, and an unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms.

According to one embodiment of the present specification, the Ar1 is a pyridine group substituted with one or more groups selected from the group consisting of a phenyl group and a pyridine group; a pyrimidine group substituted with a phenyl group; a triazine group substituted with one or more groups selected from the group consisting of a phenyl group, a naphthyl group, a pyridine group, a biphenyl group, and a dibenzofuran group; a quinazoline group substituted with a phenyl group; a quinoxaline group substituted with a phenyl group; a benzothienopyrimidine group substituted with a phenyl group; a dibenzofuran group; a carbazole group unsubstituted or substituted with a phenyl group.

According to one embodiment of the present specification, the chemical formula 1 is any one selected from the following compounds.

.

The present specification provides an organic light-emitting device comprising the heterocyclic compound described above.

When it is said in this specification that an element is located "on" another element, this includes not only cases where an element is in contact with another element, but also cases where another element exists between the two elements.

When it is said in this specification that a part "includes" a certain component, this does not exclude other components, but rather may include other components, unless otherwise specifically stated.

In this specification, the 'layer' is a term interchangeable with 'film', which is mainly used in the present technical field, and means a coating covering a target area. The size of the 'layer' is not limited, and each 'layer' may have the same or different sizes. According to one embodiment, the size of the 'layer' may be the same as the entire element, may correspond to the size of a specific functional area, and may be as small as a single sub-pixel.

In this specification, the meaning that a specific A material is included in a B layer includes both i) one or more A materials being included in one B layer, and ii) the B layer is composed of one or more layers, and the A material is included in one or more layers of the multiple B layers.

In this specification, the meaning that a specific A material is included in a C layer or a D layer means that i) it is included in at least one layer among at least one C layer, ii) it is included in at least one layer among at least one D layer, or iii) it is included in at least one C layer and at least one D layer, respectively.

The present specification provides an organic light-emitting device including a first electrode; a second electrode provided opposite the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein at least one layer of the organic layers includes a heterocyclic compound represented by the chemical formula 1.

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

According to one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes the heterocyclic compound.

According to one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes at least one heterocyclic compound.

According to one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes one kind of the heterocyclic compound.

According to one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes two kinds of the heterocyclic compounds, and the heterocyclic compounds are different from each other.

According to one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes the heterocyclic compound as a host of the light-emitting layer.

According to one embodiment of the present specification, the light-emitting layer includes a dopant, and the dopant includes a phosphorescent dopant.

According to one embodiment of the present specification, the phosphorescent dopant comprises a metal complex.

According to one embodiment of the present specification, the metal complex may be at least one of an iridium-based complex, a platinum-based complex, and a palladium-based complex, but is not limited thereto.

The above dopant may be one or more selected from the compounds exemplified below, but is not limited thereto.

Dp-28

According to one embodiment of the present specification, the light-emitting layer comprises a host and a dopant in a weight ratio of 99:1 to 1:99. Specifically, a weight ratio of 99:1 to 50:50, more specifically, a weight ratio of 99:1 to 70:30, and even more specifically, a weight ratio of 99:1 to 95:5.

According to one embodiment of the present specification, the organic light-emitting device further includes one or two or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer.

According to one embodiment of the present specification, the organic light-emitting element includes a first electrode; a second electrode provided opposite the first electrode; a light-emitting layer provided between the first electrode and the second electrode; and two or more organic layers provided between the light-emitting layer and the first electrode, or between the light-emitting layer and the second electrode.

According to one embodiment of the present specification, two or more organic layers between the light-emitting layer and the first electrode, or between the light-emitting layer and the second electrode, may include at least two selected from the group consisting of a light-emitting layer, a hole transport layer, a hole injection layer, a hole injection and transport layer, an electron blocking layer, a hole blocking layer, an electron injection layer, an electron transport layer, and an electron injection and transport layer.

According to one embodiment of the present specification, the first electrode is an anode or a cathode.

According to one embodiment of the present specification, the second electrode is a cathode or an anode.

According to one embodiment of the present specification, the organic light-emitting device may be an organic light-emitting device having a structure (normal type) in which an anode, one or more organic layers, and a cathode are sequentially laminated on a substrate.

According to one embodiment of the present specification, the organic light-emitting device may be an inverted type organic light-emitting device in which an anode, one or more organic layers, and a cathode are sequentially laminated on a substrate.

For example, the structure of an organic light-emitting device according to one embodiment of the present specification is illustrated in FIGS. 1 and 2. FIGS. 1 and 2 illustrate the organic light-emitting device and are not limited thereto.

Figure 1 illustrates the structure of an organic light-emitting device in which a first electrode (2), a light-emitting layer (4), and a second electrode (3) are sequentially laminated on a substrate (1). The heterocyclic compound of the chemical formula 1 is included in the light-emitting layer.

FIG. 2 illustrates the structure of an organic light-emitting device in which a first electrode (2), a hole injection layer (5), a hole transport layer (6), an electron blocking layer (7), a light-emitting layer (4), an electron transport layer (8), an electron injection layer (9), and a second electrode (3) are sequentially laminated on a substrate (1). The heterocyclic compound of the chemical formula 1 is included in the light-emitting layer.

The organic light-emitting device of the present specification can be manufactured using materials and methods known in the art, except that the light-emitting layer includes the compound, i.e., the heterocyclic compound represented by the chemical formula 1.

When the organic light-emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.

For example, the organic light-emitting device of the present specification can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. At this time, a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation is used to deposit a metal or a conductive metal oxide or an alloy thereof on the substrate to form an anode, and an organic layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer is formed thereon, and then a material that can be used as a cathode is deposited thereon. In addition to this method, the organic light-emitting device can be manufactured by sequentially depositing a second electrode material, an organic layer, and a first electrode material on the substrate.

In addition, the compound represented by the above chemical formula 1 can be formed into an organic layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light-emitting device. Here, the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited thereto.

In addition to this method, an organic light-emitting element can also be manufactured by sequentially depositing an organic layer, a first electrode material, and a second electrode material on a substrate. However, the manufacturing method is not limited thereto.

As the first electrode material, a material having a high work function is usually preferable so that hole injection into the organic layer can be smooth. For example, the present invention includes, but is not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO ₂ : Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

As the second electrode material, it is preferable to have a low work function so that electrons can be easily injected into the organic layer. Examples thereof include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer structures such as LiF/Al or LiO ₂ /Al.

The above-described light-emitting layer may include a host material and a dopant material. In addition to the light-emitting layer including the heterocyclic compound represented by the chemical formula 1 according to one embodiment of the present specification, when an additional light-emitting layer is included, the host material may be a condensed and/or non-condensed aromatic ring derivative or a heterocyclic compound. Specifically, the condensed aromatic ring derivatives may include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and the heterocyclic compound may include dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

The above dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, the aromatic amine derivatives are condensed aromatic ring derivatives having a substituted or unsubstituted arylamine group, such as pyrene, anthracene, chrysene, and periflanthene having an arylamine group. In addition, the styrylamine compound is a compound in which at least one arylvinyl group is substituted in a substituted or unsubstituted arylamine, and one or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group are substituted or unsubstituted. Specifically, the present invention includes, but is not limited to, styrylamine, styryldiamine, styryltriamine, and styryltetraamine. In addition, the metal complexes include, but are not limited to, iridium complexes, platinum complexes, and the like.

The above-mentioned hole injection layer is a layer that receives holes from the electrode. It is preferable that the hole injection material has the ability to transport holes, and thus has an excellent hole receiving effect from the anode and an excellent hole injection effect for the light-emitting layer or the light-emitting material. In addition, it is preferable that the material has an excellent ability to prevent the movement of excitons generated in the light-emitting layer to the electron injection layer or the electron injection material. In addition, it is preferable that the material has an excellent thin film forming ability. In addition, it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include, but are not limited to, metal porphyrin, oligothiophene, and arylamine series organic substances; hexanitrilehexaazatriphenylene series organic substances; quinacridone series organic substances; perylene series organic substances; and polythiophene series conductive polymers such as anthraquinone and polyaniline.

The above hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light-emitting layer. As the hole transport material, a material that can receive holes from the anode or the hole injection layer and transfer them to the light-emitting layer and has high hole mobility is preferable. Specific examples include, but are not limited to, arylamine-based organic compounds, conductive polymers, and block copolymers having both conjugated and non-conjugated portions.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light-emitting layer. The electron transport material is preferably a material that can well receive electrons from the cathode and transfer them to the light-emitting layer, and a material with high electron mobility is preferable. Specific examples include, but are not limited to, an Al complex of 8-hydroxyquinoline; a complex containing Alq ₃ ; an organic radical compound; a hydroxyflavone-metal complex, and the like. The electron transport layer can be used with any desired cathode material, as used according to the prior art. In particular, suitable cathode materials are conventional materials having a low work function and followed by an aluminum layer or a silver layer. Specifically, there are cesium, barium, calcium, ytterbium, and samarium, and in each case followed by an aluminum layer or a silver layer.

The above electron injection layer is a layer that receives electrons from the electrode. It is preferable that the electron injecting material has excellent electron transport ability, an electron receiving effect from the second electrode, and an excellent electron injection effect for the light-emitting layer or light-emitting material. In addition, a material that prevents excitons generated in the light-emitting layer from moving to the hole injection layer and has excellent thin film forming ability is preferable. Specific examples thereof include, but are not limited to, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone, and their derivatives, metal complex compounds, and nitrogen-containing 5-membered ring derivatives.

The above metal complex compounds include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato)gallium, Examples include, but are not limited to, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc.

The above electron blocking layer is a layer that can improve the life and efficiency of the device by preventing electrons injected from the electron injection layer from passing through the emitting layer and entering the hole injection layer. Known materials can be used without limitation, and can be formed between the emitting layer and the hole injection layer, between the emitting layer and the hole transport layer, or between the emitting layer and a layer that simultaneously injects and transports holes.

The above hole blocking layer is a layer that blocks holes from reaching the cathode, and can generally be formed under the same conditions as the electron injection layer. Specifically, examples thereof include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, and aluminum complexes.

The organic light-emitting device according to the present specification may be a front-emitting, back-emitting or double-sided emitting type depending on the material used.

Hereinafter, in order to specifically explain this specification, examples and comparative examples will be given in detail. However, the examples and comparative examples according to this specification may be modified in various different forms, and the scope of this specification is not construed as being limited to the examples and comparative examples described below. The examples and comparative examples of this specification are provided to more completely explain this specification to a person having average knowledge in the art.

<Synthetic example>

Synthesis Example 1: Preparation of Compound 1

1) Preparation of compound 1-1

Dibenzo[b,d]furan-4-ol (20 g, 109 mmol) was dissolved in 200 mL of tetrahydrofuran (THF), and the temperature was lowered to 0℃. N-Bromosuccinimide (19.3 g, 109 mmol) was added little by little. After about 1 hour, 100 mL of saturated ammonium chloride aqueous solution was added, stirred, the water layer was separated, and the organic layer was concentrated under reduced pressure. A small amount of ethyl acetate and an excess of hexane were added to the concentrated compound, and the slurry was filtered to obtain compound 1-1 as a gray solid. (22.2 g, yield 78%)

2) Preparation of compound 1-2

Compound 1-1 (20 g, 76 mmol), bis (pinacolato) diborone (26.2 g, 91.6 mmol), and potassium acetate (15.0 g, 153 mmol) were added to 240 mL of 1,4-dioxane, and 1.3 g (2.3 mmol) of dibenzylideneacetone palladium and 1.3 g (4.6 mmol) of tricyclohexylphosphine were added while stirring under reflux, and the mixture was stirred under reflux for 12 hours. After the reaction was complete, the mixture was cooled to room temperature and filtered through Celite. The filtrate was concentrated under reduced pressure, and ethyl acetate was added to the residue, dissolved, and washed with water to separate the organic layer, and then dried over anhydrous magnesium sulfate. This was distilled under reduced pressure and stirred with ethyl acetate and ethanol to produce compound 1-2 (13.0 g, yield 65%).

3) Preparation of compounds 1-3

Compound 1-2 (20 g, 64 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (18.1 g, 67.7 mmol) were dispersed in tetrahydrofuran (120 ml), 2 M potassium carbonate aqueous solution (aq. K ₂ CO ₃ ) (30 ml, 129 mmol) was added, and tetrakistriphenylphosphinopalladium [Pd(PPh ₃ ) ₄ ] (0.75 g, 1 mol%) was added, followed by stirring and refluxing for 6 hours. The temperature was lowered to room temperature, and the produced solid was filtered. The filtered filtrate was concentrated, re-dissolved in ethyl acetate, washed twice with water, separated, anhydrous magnesium sulfate was added, filtered, and concentrated. The concentrated residue was slurried with a small amount of ethyl acetate and an excess mixture of hexane and ethanol to produce compound 1-3 (12.7 g, yield 75%).

4) Preparation of compounds 1-4

Compound 1-4 (17.3 g, yield 73%) was prepared by proceeding in the same manner as in the preparation example of compound 1-1, except that compound 1-3 (20 g, 48.2 mmol) was used instead of compound dibenzo[b,d]furan-4-ol in the preparation of compound 1-1.

5) Preparation of compounds 1-5

Except that compound 1-4 (20 g, 40.6 mmol) and compound (2-fluorophenyl)boronic acid (6.3 g, 44.6 mmol) were used instead of compound 1-2 and 2-chloro-4,6-diphenyl-1,3,5-triazine in the preparation of compound 1-3, the reaction was carried out in the same manner as in the preparation example of compound 1-3, thereby preparing compound 1-5 (14.4 g, yield 70%).

6) Preparation of compound 1

Compound 1-5 (20 g, 39.3 mmol) was diluted in 100 mL of N-methyl-2-pyrrolidone, potassium carbonate (10.9 g, 78.6 mmol) was added, and the mixture was heated to 140°C. After about 1 hour, the reaction mixture was cooled to room temperature and slowly added to 1.0 L of water. The precipitated solid was filtered, dissolved in chloroform, treated with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce the target white compound 1. (13.1 g, yield 68%, MS: [M+H] ⁺ = 490)

Synthesis Example 2: Preparation of Compound 2

1) Preparation of compound 2-1

Compound 2-1 (23.1 g, yield 73%) was prepared by proceeding in the same manner as in the preparation example of compound 1-3, except that compound 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (21.0 g, 61.3 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine in the preparation of compound 1-3.

2) Preparation of compound 2-2

Compound 2-2 (16.7 g, yield 72%) was prepared by proceeding in the same manner as in the preparation example of compound 1-1, except that compound 2-1 (20 g, 40.7 mmol) was used instead of compound dibenzo[b,d]furan-4-ol in the preparation of compound 1-1.

3) Preparation of compound 2-3

Except that compound 2-2 (20 g, 40.6 mmol) and compound (2-fluorophenyl)boronic acid (5.4 g, 39 mmol) were used instead of compound 1-2 and 2-chloro-4,6-diphenyl-1,3,5-triazine in the preparation of the above Preparation Example 1-3, the reaction was carried out in the same manner as in the Preparation Example of compound 1-3, thereby preparing compound 2-3 (15.0 g, yield 73%).

4) Preparation of compound 2

The reaction was carried out in the same manner as in the preparation example of compound 1, except that compound 2-3 (20 g, 34.2 mmol) was used instead of compound 1-5 in the preparation of compound 1, to prepare the target compound 2. (16.7 g, yield 72%, MS: [M+H] ⁺ = 566)

Synthesis Example 3: Preparation of Compound 3

1) Preparation of compound 3-1

Compound 3-1 (26.7 g, yield 82%) was prepared by proceeding in the same manner as in the preparation example of compound 1-3, except that compound 1-1 (20 g, 76.4 mmol) and (9-phenyl-9H-carbazol-3-yl)boronic acid (23 g, 80.2 mmol) were used instead of compound 1-2 and 2-chloro-4,6-diphenyl-1,3,5-triazine in the preparation of compound 1-3.

2) Preparation of compound 3-2

Compound 3-2 (16.0 g, yield 68%) was prepared by proceeding in the same manner as in the preparation example of compound 1-1, except that compound 3-1 (20 g, 47.0 mmol) was used instead of compound dibenzo[b,d]furan-4-ol in the preparation of compound 1-1.

3) Preparation of compound 3-3

Except that compound 3-2 (20 g, 39.8 mmol) and compound (2-fluorophenyl)boronic acid (6.1 g, 43.7 mmol) were used instead of compound 1-2 and 2-chloro-4,6-diphenyl-1,3,5-triazine in the preparation of the above compound 1-3, the reaction was carried out in the same manner as in the preparation example of the above compound 1-3, thereby preparing compound 3-3 (15.0 g, yield 73%).

4) Preparation of compound 3

The reaction was carried out in the same manner as in the preparation example of compound 1, except that compound 3-3 (20 g, 38.5 mmol) was used instead of compound 1-5 in the preparation of compound 1, to prepare the target compound 3. (13.8 g, yield 72%, MS: [M+H] ⁺ = 500)

Synthesis Example 4: Preparation of Compound 4

1) Preparation of compound 4-1

Compound 4-1 (24.8 g, yield 77%) was prepared by proceeding in the same manner as in the preparation example of compound 1-3, except that compound 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (21.0 g, 61.3 mmol) was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine in the preparation of compound 1-3.

2) Preparation of compound 4-2

Compound 4-2 (20.9 g, yield 65%) was prepared by proceeding in the same manner as in the preparation example of compound 1-1, except that compound 4-2 (20 g, 40.7 mmol) was used instead of compound dibenzo[b,d]furan-4-ol in the preparation of compound 1-1.

3) Preparation of compound 4-3

Compound 4-3 (24.8 g, yield 77%) was prepared by proceeding in the same manner as in the preparation example of compound 1-3, except that compound 4-2 (20 g, 40.6 mmol) and compound (2-fluorophenyl)boronic acid (5.4 g, 39 mmol) were used instead of compound 1-2 and 2-chloro-4,6-diphenyl-1,3,5-triazine in the preparation of compound 1-3.

4) Preparation of compound 4

The reaction was carried out in the same manner as in the preparation example of compound 1, except that compound 4-3 (20 g, 34.2 mmol) was used instead of compound 1-5 in the preparation of compound 1, to prepare the target compound 4. (16.7 g, yield 72%, MS: [M+H] ⁺ = 566)

Fabrication of organic light-emitting devices

Example 1

A glass substrate coated with a 1,300 Å thick ITO (indium tin oxide) film was placed in distilled water containing a detergent and ultrasonically cleaned. The detergent used was a Fischer Co. product, and the distilled water used was distilled water that had been filtered twice through a Millipore Co. filter. After washing the ITO for 30 minutes, ultrasonic cleaning was performed twice with distilled water for 10 minutes. After washing with distilled water, ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, and after drying, the substrate was transported to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using oxygen plasma and then transported to a vacuum deposition device.

As described above, a hole injection layer was formed by thermal vacuum depositing the HI-1 compound as follows on the ITO transparent electrode to a thickness of 50 Å.

A hole transport layer was formed by thermally vacuum depositing the HT-1 compound to a thickness of 250 Å on the above hole injection layer, and an electron blocking layer was formed by vacuum depositing the HT-2 compound to a thickness of 50 Å on the HT-1 deposition film.

Next, compound 1 prepared in Synthesis Example 1 was deposited as a phosphorescent host on the HT-2 deposition film to a thickness of 400 Å, and phosphorescent dopant GD-1 was co-deposited at a weight ratio of 5 to 20% to form a light-emitting layer.

On the above-mentioned light-emitting layer, ET-1 material was vacuum-deposited to a thickness of 250Å, and additionally ET-2 material was co-deposited with 2% weight Li to a thickness of 100Å to form an electron transport layer and an electron injection layer. Aluminum was deposited to a thickness of 1000Å on the electron injection layer to form a cathode.

In the above process, the deposition rate of organic materials was maintained at 0.4 to 0.7 Å/sec, aluminum was maintained at 2 Å/sec, and the vacuum during deposition was maintained at 1 × 10 ^-7 to 5 × 10 ^-8 torr.

Examples 2 to 6

Except that the contents of the phosphorescent host material and the phosphorescent dopant were changed as shown in Table 1 below when forming the light-emitting layer in Example 1, organic light-emitting devices of Examples 2 to 6 were each manufactured using the same method as Example 1.

Comparative examples 1 to 5

Except that the contents of the phosphorescent host material and the phosphorescent dopant were changed as shown in Table 1 below when forming the light-emitting layer in Example 1, organic light-emitting devices of Comparative Examples 1 to 5 were each manufactured using the same method as Example 1. At this time, the host material compounds A to D used in Comparative Examples 1 to 5 are as follows.

Evaluation of organic light-emitting devices

Current was applied to the organic light-emitting devices manufactured in Examples 1 to 6 and Comparative Examples 1 to 5, and the voltage, efficiency, color coordinates, and lifespan were measured. The results are shown in Table 1 below. Here, T95 means the time required for the luminance to decrease to 95% when the initial luminance at a light density of 20 mA/cm ² is set to 100%.

division Host: Dopant
(Thickness, Å) Dopant content Voltage (V)
(@10mA/cm ² ) EQE (%)
(@10mA/cm ² ) Color coordinates
(x,y) Lifespan (T ₉₅ , h)
(@20mA/cm ² ) Example 1 Compound 1:GD-1
(400)12% 3.20 18.0 (0.32,0.62) 60.5 Example 2 Compound 2:GD-1
(400)12% 3.13 18.7 (0.32,0.61) 64.2 Example 3 Compound 4:GD-1
(400)12% 3.28 19.7 (0.32,0.63) 70.4 Example 4 Compound 1: Compound 3: GD-1
(240:160)10% 3.28 19.7 (0.32,0.63) 90.4 Example 5 Compound 2: Compound 3: GD-1
(200:200)8% 3.25 21.1 (0.33,0.63) 79.5 Example 6 Compound 1: Compound A: GD-1
(200:200)10% 3.43 18.1 (0.34,0.62) 60.9 Comparative Example 1 Compound A:GD-1
(400)12% 4.70 13.2 (0.33,0.61) 20.3 Comparative Example 2 Compound B:GD-1
(400)10% 4.57 13.2 (0.33,0.61) 26.6 Comparative Example 3 Compound C:GD-1
(400)12% 4.43 16.1 (0.32,0.62) 30.3 Comparative Example 4 Compound D:GD-1
(400)12% 3.40 17.5 (0.33,0.62) 55.4 Comparative Example 5 Compound D: Compound C: GD-1
(200:200)10% 3.52 15.5 (0.32,0.62) 57.6

In the above Table 1, the organic light-emitting device of one embodiment of the present specification may include at least one compound of the chemical formula 1, and the organic light-emitting device including the compound of the chemical formula 1 according to one embodiment of the present specification as a host of the light-emitting layer has the effects of lower driving voltage, superior external quantum efficiency, and/or longer lifespan than the organic light-emitting devices of Comparative Examples 1 to 5 including at least one of Compounds A to D. Although the preferred embodiments of the present invention have been described above, the present invention is not limited thereto, and various modifications may be made within the scope of the claims and the detailed description of the invention, and this also falls within the scope of the invention.

1: Substrate
2: First electrode
3: Second electrode
4: Emissive layer
5: Hole injection layer
6: Hole transport layer
7: Electronic barrier layer
8: Electron transport layer
9: Electron injection layer

Claims (9)

A heterocyclic compound represented by the following chemical formula 1:
[Chemical Formula 1]

In the above chemical formula 1,
L1 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group,
Ar1 is a pyridine group substituted with one or more groups selected from the group consisting of a phenyl group and a pyridine group; a pyrimidine group substituted with a phenyl group; a triazine group substituted with one or more groups selected from the group consisting of a phenyl group, a naphthyl group, a pyridine group, a biphenyl group, and a dibenzofuran group; a quinazoline group substituted with a phenyl group; a quinoxaline group substituted with a phenyl group; a benzothienopyrimidine group substituted with a phenyl group; a dibenzofuran group; or a carbazole group unsubstituted or substituted with a phenyl group,
When the substituted or unsubstituted divalent heterocyclic group of the above L1 is a substituted or unsubstituted divalent carbazole group, the substituted or unsubstituted divalent carbazole group is represented by the following chemical formula 2,
[Chemical formula 2]

In the above chemical formula 2,
Any one of R1 to R8 is of the chemical formula 1. is a part that is bonded to, and among R1 to R8, the chemical formula 1 The remaining portion that is not bonded to, and one of Ar2 is a portion that is bonded to Ar1 of the chemical formula 1,
Among the above R1 to R8 and Ar2, the chemical formula 1 Or the remaining moieties not bonded to Ar1 are the same or different from each other, and each is independently hydrogen; an aryl group or a heterocyclic group,
In the above chemical formula 1 Excluding . In claim 1, L1 is a direct bond; a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; or a divalent monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms,
A heterocyclic compound wherein the divalent C2-C30 monocyclic or polycyclic heterocyclic group of L1 is a divalent carbazole group, and the divalent carbazole group is represented by the chemical formula 2. In claim 1, the chemical formula 1 is a heterocyclic compound selected from the following compounds:

. An organic light-emitting device comprising: a first electrode; a second electrode provided facing the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein at least one of the organic layers comprises the heterocyclic compound of any one of claims 1 to 3. An organic light-emitting device according to claim 4, wherein the organic layer includes a light-emitting layer, and the light-emitting layer includes the heterocyclic compound. An organic light-emitting device according to claim 4, wherein the organic layer includes a light-emitting layer, and the light-emitting layer includes the heterocyclic compound as a host for the light-emitting layer. An organic light-emitting device according to claim 6, wherein the light-emitting layer comprises a dopant, and the dopant comprises a phosphorescent dopant. An organic light-emitting device according to claim 7, wherein the phosphorescent dopant comprises a metal complex. An organic light-emitting device according to claim 4, wherein the organic layer includes a light-emitting layer, the light-emitting layer includes a host and a dopant, and the host and the dopant are included in a weight ratio of 99:1 to 70:30.