KR102732793B1 - Compound and organic light emitting device comprising same - Google Patents

Abstract

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

Description

COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING SAME

The present specification relates to a 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.

Republic of Korea Patent Publication No. 2000-0051826

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

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

[Chemical Formula 1]

In the above chemical formula 1,

One of R ₁ to R ₁₀ is represented by the following chemical formula 1-A, and the other is a substituted or unsubstituted aryl group,

The remainder of R ₁ to R ₁₀ are the same as or different from each other, and each independently represents deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; or a substituted or unsubstituted aryl group,

[Chemical Formula 1-A]

In the above chemical formula 1-A,

X ₁ is O or S,

One of R ₁₀₁ to R ₁₀₈ is a moiety bonded to chemical formula 1, and the other is represented by the following chemical formula 1-B,

The remainder of R ₁₀₁ to R ₁₀₈ are the same as or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

[Chemical Formula 1-B]

In the above chemical formula 1-B,

X ₂ is O or S,

R ₂₀₁ to R ₂₀₅ are the same as or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

* is a part that combines with chemical formula 1-A.

In addition, other embodiments of the present specification are:

An organic light-emitting device comprising a first electrode; a second electrode; and at least one organic layer provided between the first electrode and the second electrode,

An organic light-emitting device is provided, wherein at least one of the organic layers comprises a compound of the above-described chemical formula 1.

A compound according to one embodiment of the present specification can be used in an organic light-emitting device, thereby lowering the driving voltage of the organic light-emitting device and improving the luminous efficiency. In addition, the life characteristics of the device can be improved due to the thermal stability of the compound.

Figure 1 illustrates an example of an organic light-emitting device according to one embodiment of the present specification.
FIG. 2 illustrates an example of an organic light-emitting device according to one embodiment of the present specification.
Figure 3 is an MS graph of compound A.

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

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

Chemical formula 1 according to one embodiment of the present specification is a structure in which specific functional groups, Chemical formula 1-A and Chemical formula 1-B, are simultaneously bonded to an anthracene structure, and has excellent electron transfer and hole transfer capabilities and high quantum efficiency. Therefore, by applying the compound of Chemical formula 1 to an organic layer of an organic light-emitting device, the effects of reduced driving voltage, improved efficiency, and longer lifespan can be observed.

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; a condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring; and a heterocyclic group, or substituted with a substituent in which two or more of the above-mentioned substituents are linked, or having no substituents.

In this specification, the connection of two or more substituents means that the hydrogen of one substituent is connected to another substituent. For example, the connection of two substituents means that a phenyl group and a naphthyl group are connected. or can be a substituent of. In addition, the connection of three substituents includes not only the connection of (substituent 1)-(substituent 2)-(substituent 3) in sequence, but also the connection of (substituent 2) and (substituent 3) to (substituent 1). For example, a phenyl group, a naphthyl group, and an isopropyl group are connected. , , or can be a substituent of. The above definition also applies equally to cases where four or more substituents are connected.

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]heptyl 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 substituted aryl group may include a structure in which an aliphatic hydrocarbon ring is condensed with the aryl group. According to one embodiment, the substituted aryl group may include a tetrahydronaphthalene group, and more specifically, (1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene group) may be included, but is not limited thereto.

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 or forms a ring, 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 decahydrobenzocarbazole group, a hexahydrocarbazole group, a dihydrobenzoazacilline group, a dihydroindenocarbazole group, a spirofluorenxanthene group, a spirofluorentioxanthene 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 -BY ₁₀₀ Y ₁₀₁ , wherein Y ₁₀₀ and Y 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 dimethyl boron group, a diethyl boron group, a t-butylmethyl boron group, a diphenyl boron group, and the like.

In the present specification, the amine group may 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 amine groups include, but are not limited to, 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, an N-phenylbiphenylamine group, an N-phenylnaphthylamine group, an N-biphenylnaphthylamine group, an N-naphthylfluorenylamine group, an N-phenylphenanthrenylamine group, an N-biphenylphenanthrenylamine group, an N-phenylfluorenylamine group, an N-phenylterphenylamine group, an N-phenanthrenylfluorenylamine group, an N-biphenylfluorenylamine group, and the like.

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 the present specification, the hydrocarbon ring group may be an aromatic hydrocarbon ring group, an aliphatic hydrocarbon ring group, or a condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and may be selected from examples of a cycloalkyl group, an aryl group, and a combination thereof, and the hydrocarbon ring group may be, but is not limited to, a phenyl group, a cyclohexyl group, an adamantyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.1]octyl group, a tetrahydronaphthalene group, a tetrahydroanthracene group, a 1,2,3,4-tetrahydro-1,4-methanonaphthalene group, a 1,2,3,4-tetrahydro-1,4-ethanonaphthalene group, a spirocyclopentanefluorene group, a spiroadamantanefluorene group, and a spirocyclohexanefluorene group. no.

In the present specification, the meaning of “adjacent” in “forming a ring by bonding with adjacent groups” is the same as described above, and the “ring” means a substituted or unsubstituted hydrocarbon ring; or a substituted or unsubstituted heterocycle.

In the present specification, the hydrocarbon ring may be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a condensed ring of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and may be selected from examples of a cycloalkyl group, an aryl group, and a combination thereof, except for the non-monovalent ones, and the hydrocarbon ring may be selected from benzene, cyclohexane, adamantane, bicyclo[2.2.1]heptane, bicyclo[2.2.1]octane, tetrahydronaphthalene, tetrahydroanthracene, 1,2,3,4-tetrahydro-1,4-methanonaphthalene, 1,2,3,4-tetrahydro-1,4-ethanonaphthalene, spirocyclopentanefluorene, spiroadamantanefluorene, and spirocyclohexanefluorene, but is not limited thereto.

In the present specification, a heterocycle 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. The heterocycle may be monocyclic or polycyclic, and may be an aromatic, aliphatic, or a condensed ring of aromatic and aliphatic groups, and the aromatic heterocycle may be selected from examples of heteroaryl groups among the heterocyclic groups, except that it is not monovalent.

In this specification, an aliphatic heterocycle means an aliphatic ring containing at least one heteroatom. Examples of aliphatic heterocycles include, but are not limited to, oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, azocaine, thiocane, tetrahydronaphthothiophene, tetrahydronaphthofuran, tetrahydrobenzothiophene, and tetrahydrobenzofuran.

In the present specification, examples of condensed heterocycles of aliphatic or aromatic and aliphatic include, but are not limited to, tetrahydrobenzonaphthothiophene and tetrahydrobenzonaphthofuran.

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

Unless otherwise defined herein, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. Although methods and materials similar or equivalent to those described herein can be used in the practice or testing of embodiments of the present invention, suitable methods and materials are described below. All publications, patent applications, patents, and other references mentioned in this specification are incorporated herein by reference in their entirety, and in case of conflict, this specification, including definitions, will control unless a specific passage is cited. Furthermore, the materials, methods, and examples are illustrative only and not intended to be limiting.

Hereinafter, the compound of the above chemical formula 1 will be described in detail.

According to one embodiment of the present specification, R ₉ of the chemical formula 1 is represented by chemical formula 1-A, any one of R ₁₀₅ to R ₁₀₈ of the chemical formula 1-A is bonded to chemical formula 1, and any one of R ₁₀₁ to R ₁₀₄ of the chemical formula 1-A is represented by chemical formula 1-B.

According to one embodiment of the present specification, R ₉ of the chemical formula 1 is represented by chemical formula 1-A, one of R ₁₀₅ to R ₁₀₈ of the chemical formula 1-A is bonded to chemical formula 1, and the other one of R ₁₀₅ to R ₁₀₈ of the chemical formula 1-A is represented by chemical formula 1-B.

According to one embodiment of the present specification, R ₉ of the chemical formula 1 is represented by chemical formula 1-A, R ₁₀ is an aryl group unsubstituted or substituted with at least one of deuterium and an aryl group; or an aryl group in which an aliphatic hydrocarbon ring is condensed, and R ₁ to R ₈ are each independently deuterium; or a substituted or unsubstituted aryl group.

According to one embodiment of the present specification, R ₁₀ of the chemical formula 1 is a phenyl group unsubstituted or substituted with at least one of a deuterium atom and an aryl group; a biphenyl group unsubstituted or substituted with a deuterium atom; a terphenyl group unsubstituted or substituted with a deuterium atom; a naphthyl group unsubstituted or substituted with at least one of a deuterium atom and an aryl group; a phenanthrene group unsubstituted or substituted with at least one of a deuterium atom and an aryl group; or a triphenylene group unsubstituted or substituted with at least one of a deuterium atom and an aryl group.

According to one embodiment of the present specification, R ₁₀ of the chemical formula 1 is a phenyl group unsubstituted or substituted with one or more of a deuterium atom, a naphthyl group, a phenanthrene group, a chrysene group, a triphenylene group, and a pyrene group; a biphenyl group unsubstituted or substituted with a deuterium atom; a terphenyl group unsubstituted or substituted with a deuterium atom; a naphthyl group unsubstituted or substituted with one or more of a deuterium atom, a phenyl group, and a naphthyl group; a phenanthrene group unsubstituted or substituted with one or more of a deuterium atom and a phenyl group; or a triphenylene group unsubstituted or substituted with a deuterium atom.

According to one embodiment of the present specification, R ₇ of the chemical formula 1 is represented by chemical formula 1-A, R ₉ and R ₁₀ are each independently an aryl group unsubstituted or substituted with at least one of deuterium and an aryl group; or an aryl group in which an aliphatic hydrocarbon ring is condensed, and R ₁ to R ₆ and R ₈ are all deuterium.

According to one embodiment of the present specification, one of R ₁₀₁ to R ₁₀₈ of the chemical formula 1-A is a moiety bonded to chemical formula 1, the other is represented by the following chemical formula 1-B, and the rest are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group.

According to one embodiment of the present specification, X ₁ of the chemical formula 1-A is O.

According to one embodiment of the present specification, X ₁ of the chemical formula 1-A is S.

According to one embodiment of the present specification, X ₂ of the chemical formula 1-B is O.

According to one embodiment of the present specification, X ₂ of the chemical formula 1-B is S.

According to one embodiment of the present specification, the chemical formula 1 contains at least one deuterium.

According to one embodiment of the present specification, the meaning of "at least one comprises deuterium" means that at least one of the hydrogens at the substitutable positions is substituted with deuterium or is substituted with a substituent substituted with deuterium. The substituent includes a substituent defined in the "substituted or unsubstituted" above.

According to one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 is 0.01% to 100%.

According to one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 is 0.1% to 100%.

According to one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 is 1% to 100%.

According to one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 is 40% to 99%.

According to one embodiment of the present specification, when the chemical formula 1 contains deuterium, the following effects are provided. Specifically, the physicochemical properties, such as the chemical bond length related to deuterium, are different from those of hydrogen, and the elongation amplitude of the C-D bond is smaller than that of the C-H bond, so that the van der Waals radius of deuterium is smaller than that of hydrogen, and in general, the C-D bond can be shown to be shorter and stronger than the C-H bond. Therefore, when hydrogen at a substitutable position in the chemical formula 1 is substituted with deuterium, the energy of the ground state is lowered, and as the bond length of deuterium and carbon becomes shorter, the molecular hardcore volume decreases, and accordingly, the electrical polarizability can be reduced, and the intermolecular interaction can be weakened, thereby increasing the thin film volume. In addition, these characteristics can have the effect of lowering the crystallinity of the thin film, that is, creating an amorphous state, and can be effective in generally increasing the lifespan and operating characteristics of organic light-emitting devices, and heat resistance can be improved compared to conventional organic light-emitting devices.

As used herein, “containing deuterium,” “deuterated,” or “deuterated” means that a hydrogen at a substitutable position of a compound is replaced with deuterium.

As used herein, “perdeuterated” means a compound or group in which all hydrogens in the molecule are replaced with deuterium, and has the same meaning as “100% deuterated.”

In the present specification, "X% deuterated", "degree of deuteration X%", or "deuterium substitution rate X%" means that X% of hydrogens at substitutable positions in the structure are replaced with deuterium. For example, when the structure is dibenzofuran, "25% deuterated" of the dibenzofuran, "degree of deuteration 25%" of the dibenzofuran, or "deuterium substitution rate 25%" of the dibenzofuran means that 2 of 8 hydrogens at substitutable positions of the dibenzofuran are replaced with deuterium.

In this specification, the “degree of deuteration” or “deuterium substitution rate” can be determined by a known method such as nuclear magnetic resonance spectroscopy ( ¹ H NMR), thin-layer chromatography/mass spectrometry (TLC/MS), or gas chromatography/mass spectrometry (GC/MS).

Specifically, when analyzing the "degree of deuteration" or "deuterium substitution rate" by nuclear magnetic resonance spectroscopy ( ^1H NMR), by adding DMF (dimethylformamide) as an internal standard, the degree of deuteration or deuterium substitution rate can be calculated from the total peak integration amount through the integration ratio on ^1H NMR.

In addition, when analyzing the "deuteration degree" or "deuterium substitution rate" through TLC/MS (Thin-Layer Chromatography/Mass Spectrometry), the substitution rate can be calculated based on the maximum value (median value) of the distribution of molecular weights at the end of the reaction. For example, when analyzing the deuteration degree of Compound A below, when the molecular weight of the starting material below is 506 and the maximum molecular weight value (median value) of Compound A below is 527 in the MS graph of FIG. 3, since 21 of the hydrogens (26) at substitutable positions of the starting material below were substituted with deuterium, it can be calculated that approximately 81% of the hydrogens were deuterated.

In this specification, D means deuterium.

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

According to one embodiment of the present specification, the band gap of the compound of chemical formula 1 is 2.9 eV or more.

According to one embodiment of the present specification, the band gap of the compound of chemical formula 1 is 2.9 eV to 4.0 eV.

Specifically, the organic compound used in the organic light-emitting device must have a band gap of 0.5 eV to 4.0 eV to function as an organic semiconductor, and a band gap energy of at least 2.9 eV or more is required to exhibit blue light. According to the principle of fluorescence blue emission of the host-dopant system, the band gap of the blue fluorescent host must be larger than the band gap of the blue fluorescent dopant so that energy transfer occurs smoothly. Therefore, it is preferable that the blue fluorescent host have an energy band gap of 2.9 eV to 4.0 eV.

In this specification, "energy level" means energy size. Therefore, the energy level is interpreted as meaning the absolute value of the corresponding energy value. For example, a low or deep energy level means that the absolute value increases in the minus direction from the vacuum level.

In this specification, HOMO (highest occupied molecular orbital) means a molecular orbital (highest occupied molecular orbital) in which electrons are in the highest energy region in which they can participate in bonding, LUMO (lowest unoccupied molecular orbital) means a molecular orbital (lowest unoccupied molecular orbital) in which electrons are in the lowest energy region among antibonding regions, and HOMO energy level means the distance from a vacuum level to HOMO. In addition, LUMO energy level means the distance from a vacuum level to LUMO.

In this specification, the HOMO energy level can be measured using an atmospheric photoelectron spectrometer (manufactured by RIKEN KEIKI Co., Ltd.: AC3), and the LUMO energy level can be calculated using a wavelength value measured through photoluminescence (PL).

In this specification, band gap means the difference between the HOMO energy level and the LUMO energy level.

The present specification provides an organic light-emitting device comprising the 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.

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 one or more organic layers provided between the first electrode and the second electrode, wherein at least one of the organic layers includes a compound of 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 compound.

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

According to one embodiment of the present specification, the fluorescent dopant is a pyrene-based compound or a non-pyrene-based compound.

According to one embodiment of the present specification, the non-pyrene compound includes a boron compound.

According to one embodiment of the present specification, the light-emitting layer further includes at least one host different from the compound of the chemical formula 1. That is, the light-emitting layer may have two or more hosts.

According to one embodiment of the present specification, the two or more hosts include at least one first anthracene derivative containing deuterium, and at least one second anthracene derivative not containing deuterium, and either the first anthracene derivative or the second anthracene derivative may be a compound of the chemical formula 1.

According to one embodiment of the present specification, the two or more hosts include two or more first anthracene derivatives containing deuterium, and one of the two first anthracene derivatives may be a compound of the chemical formula 1.

Any host different from the compound of the above chemical formula 1 may be used without limitation as long as it is an anthracene host used in the art, as long as it is different from the above chemical formula 1, and is not limited thereto.

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

According to one embodiment of the present specification, the light-emitting layer includes a host and a dopant, and the host includes a compound represented by the chemical formula 1.

According to one embodiment of the present specification, the dopant is a blue dopant.

According to one embodiment of the present specification, the organic light-emitting device is a blue organic light-emitting device.

According to one embodiment of the present specification, the light-emitting layer includes two or more mixed hosts, and at least one of the two or more mixed hosts includes a compound represented by the chemical formula 1.

According to one embodiment of the present specification, the light-emitting layer includes two or more mixed hosts, at least one of the two or more mixed hosts includes a compound represented by the chemical formula 1, and the rest include anthracene compounds different from the chemical formula 1.

Among the two or more mixed hosts above, at least one of which includes a compound represented by the chemical formula 1, and the rest are different from the chemical formula 1, and any anthracene host used in the art may be used without limitation, but is not limited thereto.

According to one embodiment of the present specification, the light-emitting layer may be a single layer in which two or more hosts are mixed.

According to one embodiment of the present specification, the light-emitting layer is a laminated structure including two or more light-emitting layers, and the two or more light-emitting layers may each include different hosts.

An organic light-emitting device using two or more mixed hosts according to one embodiment of the present specification is intended to improve the performance of the device by mixing the advantages of each host. For example, when two hosts are mixed, an organic light-emitting device having the effects of high efficiency, low voltage, and long life can be manufactured by mixing one host having the effects of high efficiency and low voltage and one host having the effects of long life.

According to one embodiment of the present specification, the light-emitting layer has two or more layers, and at least one layer among the two or more light-emitting layers includes the compound of the chemical formula 1.

According to one embodiment of the present specification, the light-emitting layer has two or more layers, at least one layer of the two or more light-emitting layers includes two or more mixed hosts, and at least one of the two or more mixed hosts includes the compound of the chemical formula 1.

According to one embodiment of the present specification, the light-emitting layer is two-layered, and one of the two light-emitting layers includes the compound of chemical formula 1.

According to one embodiment of the present specification, the light-emitting layer is two-layered, and one of the two light-emitting layers includes two or more mixed hosts, and at least one of the two or more mixed hosts includes a compound of the chemical formula 1.

The above two or more mixed hosts are the same as described above.

According to one embodiment of the present specification, the organic light-emitting device is a blue organic light-emitting device having a maximum emission wavelength (λ _max ) of an emission spectrum of 400 nm to 470 nm.

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

According to one embodiment of the present specification, the light-emitting layer includes a host and a dopant, and the dopant includes at least one selected from a pyrene-based compound and a non-pyrene-based compound.

The above pyrene-based compounds and non-pyrene-based compounds can be used without limitation as long as they are compounds used in the art, and are not limited thereto.

According to one embodiment of the present specification, the non-pyrene compound includes a boron compound.

According to one embodiment of the present specification, the light-emitting layer includes a host and a dopant, the host includes a compound represented by the chemical formula 1, and the dopant includes at least one selected from a pyrene-based compound and a non-pyrene-based compound.

According to one embodiment of the present specification, the light-emitting layer includes a host and a dopant, and the light-emitting layer includes the host:dopant in a weight ratio of 0.1:99.9 to 20:80.

According to another embodiment of the present specification, the invention further includes a capping layer provided on an opposite surface of at least one of the first electrode and the second electrode, the surface facing the organic layer.

The above capping layer is formed to prevent a significant amount of light from being lost through total reflection in the organic light-emitting element, and the capping layer has the performance to sufficiently protect the lower cathode and light-emitting layer from external moisture penetration or contamination, and has a high refractive index to prevent light loss due to total reflection.

According to another embodiment of the present specification, the capping layer may be provided on each of a surface opposite to a surface of the first electrode facing the organic layer and a surface opposite to a surface of the second electrode facing the organic layer.

According to another embodiment of the present specification, the capping layer may be provided on an opposite surface of the surface of the first electrode facing the organic layer.

According to another embodiment of the present specification, the capping layer may be provided on each of the opposite surfaces of the surface of the second electrode facing the organic layer.

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, two or more hole transport layers are included between the light-emitting layer and the first electrode. The two or more hole transport layers may include materials that are the same or different from each other.

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 material 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 a cathode, one or more organic material layers, and an anode 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. The above FIGS. 1 and 2 illustrate an organic light-emitting device and are not limited thereto.

Fig. 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 compound 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), a hole control layer (7), an emission layer (4), an electron control layer (8), an electron transport layer (9), an electron injection layer (10), a second electrode (3), and a capping layer (11) are sequentially laminated on a substrate (1). The compound is included in the emission 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 compound of 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 compound of 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 heterocycle-containing compound, etc. Specifically, the condensed aromatic ring derivatives may include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and the heterocycle-containing compounds may include, but are not limited to, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc.

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.

According to one embodiment of the present specification, the dopant material includes, but is not limited to, a compound of the following chemical formula D-1 or D-2.

[Chemical Formula D-1]

In the above chemical formula D-1,

L101 and L102 are the same or different from each other, and each independently represents a direct bond; or a substituted or unsubstituted arylene group,

Ar101 to Ar104 are the same or different from each other, and each independently represents a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

[Chemical Formula D-2]

In the above chemical formula D-2,

T1 to T5 are the same or different from each other, and each independently represents hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amine group; or a substituted or unsubstituted aryl group,

t3 and t4 are integers from 1 to 4, respectively.

t5 is an integer from 1 to 3,

When the above t3 is 2 or more, the above 2 or more T3 are the same or different from each other,

If the above t4 is 2 or more, the above 2 or more T4 are equal to or different from each other,

When the above t5 is 2 or more, the two or more T5 are equal to or different from each other.

According to one embodiment of the present specification, L101 and L102 are direct bonds.

According to one embodiment of the present specification, Ar101 to Ar104 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

According to one embodiment of the present specification, Ar101 to Ar104 are the same as or different from each other, and are each independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, substituted or unsubstituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

According to one embodiment of the present specification, Ar101 to Ar104 are the same as or different from each other, and are each independently a phenyl group substituted with a methyl group; or a dibenzofuran group.

According to one embodiment of the present specification, the chemical formula D-1 is represented by the following compound.

According to one embodiment of the present specification, T1 to T5 are the same as or different from each other, and are each independently hydrogen; a substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic arylamine group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to one embodiment of the present specification, T1 to T5 are the same as or different from each other, and are each independently hydrogen; a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic arylamine group having 6 to 30 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms which is unsubstituted or substituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms.

According to one embodiment of the present specification, T1 to T5 are the same as or different from each other, and are each independently hydrogen; a methyl group; a tert-butyl group; a diphenylamine group; or a phenyl group substituted or unsubstituted with a methyl group or a tert-butyl group.

According to one embodiment of the present specification, the chemical formula D-2 is represented by the following compound.

The above 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, so that it has a hole receiving effect from the anode and an excellent hole injection effect into the light-emitting layer or the light-emitting material. In addition, it is preferable that it is a material that 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 it is a material that 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 organic compounds of the metal porphyrin, oligothiophene, and arylamine series; organic compounds of the hexanitrilehexaazatriphenylene series; organic compounds of the quinacridone series; organic compounds of the perylene series; Examples include, but are not limited to, conductive polymers of the polythiophene series, such as anthraquinone and polyaniline.

According to one embodiment of the present specification, the hole injection layer includes, but is not limited to, a compound of the following chemical formula HI-1.

[chemical formula HI-1]

In the above chemical formula HI-1,

At least one of X'1 to X'6 is N, and the rest are CH,

R309 to R314 are the same as or different from each other, and are each independently hydrogen; deuterium; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or combine with adjacent groups to form a substituted or unsubstituted ring.

According to one embodiment of the present specification, X'1 to X'6 are N.

According to one embodiment of the present specification, R309 to R314 are cyano groups.

According to one embodiment of the present specification, the chemical formula HI-1 is represented by the following compound.

The above hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light-emitting layer. As the hole transport material, a material having high hole mobility is preferable, which can receive holes from the anode or the hole injection layer and transfer them to the light-emitting layer. 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 above-mentioned hole control layer is a layer that can improve the lifespan and efficiency of the device by controlling the holes transported from the hole transport layer to be smoothly injected into the light-emitting layer and preventing the electrons injected from the electron injection layer from entering the hole injection layer through the light-emitting layer. Known materials can be used without limitation, and can be formed between the light-emitting layer and the hole injection layer, between the light-emitting layer and the hole transport layer, or between the light-emitting layer and a layer that simultaneously injects and transports holes.

According to one embodiment of the present specification, the hole transport layer or hole control layer includes, but is not limited to, a compound of the following chemical formula HT-1.

[chemical formula HT-1]

In the above chemical formula HT-1,

R315 to R317 are the same as or different from each other, and each independently represents one selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and a combination thereof, or are combined with adjacent groups to form a substituted or unsubstituted ring,

r315 is an integer from 1 to 5, and when r315 is 2 or more, two or more R315 are the same as or different from each other,

r316 is an integer from 1 to 5, and when r316 is 2 or more, two or more R316 are the same as or different from each other.

According to one embodiment of the present specification, R317 is any one selected from the group consisting of a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and a combination thereof.

According to one embodiment of the present specification, R317 is any one selected from the group consisting of a carbazole group; a phenyl group; a biphenyl group; and combinations thereof.

According to one embodiment of the present specification, R315 and R316 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group, or combine with an adjacent group to form an aromatic hydrocarbon ring substituted with an alkyl group.

According to one embodiment of the present specification, R315 and R316 are the same as or different from each other, and are each independently a phenyl group or a phenanthrene group, or combine with an adjacent group to form an indene substituted with a methyl group.

According to one embodiment of the present specification, the chemical formula HT-1 is represented by any one of the following compounds.

The above electron control layer is a layer that controls the smooth injection of electrons transferred from the electron transport layer into the light-emitting layer, and any known material can be used without limitation.

According to one embodiment of the present specification, the electronic control layer includes, but is not limited to, a compound of the following chemical formula EG-1.

[Chemical formula EG-1]

In the above chemical formula EG-1,

At least one of G'1 to G'18 is -L5-Ar5, and the others are hydrogen, or G'1 and G'18 are connected by -L51- to form a substituted or unsubstituted ring,

L5 is a direct bond; or a substituted or unsubstituted arylene group,

Ar5 is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

L51 is O; or S.

According to one embodiment of the present specification, the L51 is O.

According to one embodiment of the present specification, the L51 is S.

According to one embodiment of the present specification, G'1 and G'18 are linked by -L51- to form a substituted or unsubstituted heterocycle.

According to one embodiment of the present specification, G'1 and G'18 are linked by -L51- to form a substituted or unsubstituted xanthene ring; or a substituted or unsubstituted thioxanthene ring.

According to one embodiment of the present specification, G'1 and G'18 are linked by -O- to form a substituted or unsubstituted xanthene ring.

According to one embodiment of the present specification, G'1 and G'18 are linked by -S- to form a substituted or unsubstituted thioxanthene ring.

According to one embodiment of the present specification, G'1 and G'18 are linked with -O- to form a xanthene ring.

According to one embodiment of the present specification, G'1 and G'18 are linked with -S- to form a thioxanthene ring.

According to one embodiment of the present specification, L5 is a direct bond; or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

According to one embodiment of the present specification, L5 is a direct bond; or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

According to one embodiment of the present specification, L5 is a direct bond; or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

According to one embodiment of the present specification, L5 is a direct bond; or a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

According to one embodiment of the present specification, L5 is a direct bond; or a phenylene group.

According to one embodiment of the present specification, Ar5 is a substituted or unsubstituted triazine group.

According to one embodiment of the present specification, Ar5 is a triazine group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to one embodiment of the present specification, Ar5 is a triazine group substituted with a phenyl group.

According to one embodiment of the present specification, the EG-1 is represented by the following compound.

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 a material that can well receive electrons from the cathode and transfer them to the light-emitting layer, and a material having high electron mobility is preferable. Specific examples include, but are not limited to, Al complexes of 8-hydroxyquinoline; complexes containing Alq ₃ ; organic radical compounds; hydroxyflavone-metal complexes, and the like. The electron transport layer can be used with any desired cathode material, as used in 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.

According to one embodiment of the present specification, the electron transport layer includes, but is not limited to, a compound represented by the following chemical formula ET-1.

[chemical formula ET-1]

In the above chemical formula ET-1,

At least one of Z11 to Z13 is N, and the others are CH,

L601 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,

Ar601 and Ar602 are the same or different from each other, and each independently represents a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

l601 is an integer from 1 to 5, and when l601 is 2 or more, 2 or more L601 are equal to or different from each other.

According to one embodiment of the present specification, L601 is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

According to one embodiment of the present specification, the L601 is a phenylene group; a biphenylylene group; or a naphthylene group.

According to one embodiment of the present specification, Ar601 and Ar602 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to one embodiment of the present specification, Ar601 and Ar602 are phenyl groups.

According to one embodiment of the present specification, the chemical formula ET-1 is represented by the following compound.

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 holes 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 above capping layer is formed to prevent a significant amount of light from being lost through total reflection in the organic light-emitting element, and the capping layer has the performance to sufficiently protect the lower cathode and light-emitting layer from external moisture penetration or contamination, has a high refractive index, can prevent light loss due to total reflection, and can use conventional materials without limitation.

According to one embodiment of the present specification, the capping layer includes, but is not limited to, a compound represented by the following chemical formula CP-1.

[Chemical formula CP-1]

In the above chemical formula CP-1,

L501 and L502 are the same or different from each other, and each independently represents a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,

R501 and Ar501 to Ar504 are the same or different, and each independently represents a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or adjacent groups are combined with each other to form a substituted or unsubstituted ring.

According to one embodiment of the present specification, L501 and L502 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

According to one embodiment of the present specification, L501 and L502 are phenylene groups.

According to one embodiment of the present specification, R501 and Ar501 to Ar504 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or combines with an adjacent group to form a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms.

According to one embodiment of the present specification, R501 and Ar501 to Ar504 are phenyl groups, or are bonded to adjacent groups to form carbazole substituted or unsubstituted with a phenyl group.

According to one embodiment of the present specification, Ar501 combines with L501 to form a carbazole substituted with a phenyl group.

According to one embodiment of the present specification, Ar503 combines with L503 to form a carbazole substituted with a phenyl group.

According to one embodiment of the present specification, the chemical formula CP-1 is represented by the following compound.

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.

The organic light-emitting device according to the present specification can be included and used in various electronic devices. For example, the electronic device can be a display panel, a touch panel, a solar module, a lighting device, etc., but is not limited thereto.

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.

<Example>

<Manufacturing Example 1> Synthesis of Chemical Formula M1 or M2

In the above reaction formula, X ₁ is O or S,

R ₉ is hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

n is an integer from 0 to 2, and m is an integer from 0 to 4.

After adding SM1 (1 eq) and SM2 (1.05 eq) to tetrahydrofuran (excess), 2 M potassium carbonate aqueous solution (30 volume ratio with respect to THF) was added, tetrakistriphenyl-phosphinopalladium (2 mol%) was added, and the mixture was heated and stirred for 10 hours. The temperature was lowered to room temperature, and after the reaction was terminated, the potassium carbonate aqueous solution was removed and the layers were separated. After confirming the termination of the reaction, extraction was performed at room temperature to remove the solvent, and potassium carbonate (1.5 eq) and dimethylformamide (excess) were added, heated, and stirred under reflux for 5 hours. After confirming the termination of the reaction, water (1.5 volume ratio with respect to the introduced dimethylformamide) was added, and the precipitated solid was filtered. The solid was extracted with chloroform and water, and then purified by recrystallization using chloroform and ethanol to produce the above chemical formula M1 or M2.

In the synthesis method of the above chemical formula M1 or M2, M1-1 to M1-15 of Table 1 below were synthesized and M2-1 to M2-15 of Table 2 below were synthesized in the same manner, except that SM1 and SM2 were changed as shown in Tables 1 and 2 below.

[Table 1]

[Table 2]

<Manufacturing Example 2> Synthesis of chemical formula T1 or T2

In the above reaction formula, X ₁ is O or S,

R ₉ is hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

m is an integer from 0 to 6.

SM1 (1 eq, the chemical formula M synthesized above) was added to tetrachloroethane (excess) and SM2 (10 eq, <pre-mixed solution (D2O: Tf2O = 4: 1 ratio>) was added dropwise, and stirred at 140°C for 1 hour. After cooling to room temperature, extraction was performed with a saturated sodium bicarbonate aqueous solution, layers were separated, and ethanol was added to filter the solidified compound. The above process was repeated once more, and recrystallized with ethyl acetate and ethanol to prepare the chemical formula T1 or T2.

In the synthesis method of the above chemical formula T1 or T2, T1-1 to T1-5 in Table 3 below were synthesized by the same method, and T2-1 to T2-5 in Table 4 below were synthesized, except that SM1 and SM2 were changed as shown in Tables 3 and 4 below.

[Table 3]

[Table 4]

<Manufacturing Example 3> Synthesis of chemical formula N1 or N2

In the above reaction formula, X ₁ and X ₂ are each independently O or S,

R ₉ is hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

m is an integer from 0 to 6,

R ₂₀₁ to R ₂₀₅ are the same as or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

After adding SM1 (1 eq, the above-synthesized chemical formula M or T) and SM2 (1.1 eq) to tetrahydrofuran (excess), 2 M potassium carbonate aqueous solution (30 volume ratio with respect to THF) was added, and tetrakistriphenyl-phosphinopalladium (2 mol%) was added, and the mixture was heated and stirred at 85°C for 10 hours. After lowering the temperature to room temperature and terminating the reaction, the potassium carbonate aqueous solution was removed to separate the layers, and the mixture was crystallized with ethyl acetate and ethanol to produce the chemical formula N1 or N2.

In the synthesis method of the above chemical formula N1 or N2, N1-1 to N1-18 in Table 5 were synthesized and N2-1 to N2-20 in Table 6 were synthesized in the same manner, except that SM1 and SM2 were changed as shown in Tables 5 and 6 below.

[Table 5]

[Table 6]

<Manufacturing Example 4> Synthesis of chemical formula W1 or W2

In the above reaction formula, X ₁ and X ₂ are each independently O or S,

R ₉ is hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

m is an integer from 0 to 6,

R ₂₀₁ to R ₂₀₅ are the same as or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

SM1 (1 eq, the synthesized chemical formula N above) and SM2 (1.3 eq) were added to 1,4-dioxane (12 times the mass ratio compared to SM1), potassium acetate (3 eq) was added, stirred and refluxed. Palladium acetate (0.02 eq) and tricyclohexylphosphine (0.04 eq) were added after stirring in 1,4-dioxane for 5 minutes, and after 2 hours, the reaction was confirmed to be complete and cooled to room temperature. After adding ethanol and water, filtering was performed and recrystallization with ethyl acetate and ethanol was purified to produce the chemical formula W1 or W2 above.

In the synthesis method of the above chemical formula W1 or W2, W-1 to W1-18 of Table 7 below were synthesized and W2-1 to W2-20 of Table 8 below were synthesized in the same manner, except that SM1 and SM2 were changed as shown in Tables 7 and 8 below.

[Table 7]

[Table 8]

<Manufacturing Example 5> Synthesis of Chemical Formula A1 or A2

In the above reaction formula, X ₁ and X ₂ are each independently O or S,

R ₉ is hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

m is an integer from 0 to 6,

y is the number of deuterium,

R ₂₀₁ to R ₂₀₅ are the same as or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

R ₁ to R ₈ , and R' are each independently deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; or a substituted or unsubstituted aryl group.

After adding SM1 (1 eq) and SM2 (1.1 eq) to tetrahydrofuran (excess), 2 M potassium carbonate aqueous solution (30 volume ratio with respect to THF) was added, and tetrakistriphenyl-phosphinopalladium (2 mol%) was added, and the mixture was heated and stirred at 85°C for 10 hours. After lowering the temperature to room temperature and terminating the reaction, the potassium carbonate aqueous solution was removed, the layers were separated, and recrystallized with chloroform and ethyl acetate to produce the chemical formula A1 or A2.

In the synthesis method of the above chemical formula A1 or A2, A1-1 to A1-16 of Table 9 below were synthesized and A2-1 to A2-19 of Table 10 below were synthesized in the same manner, except that SM1 and SM2 were changed as shown in Tables 9 and 10 below.

[Table 9]

[Table 10]

The following examples are examples of the scheme of SM2 used in the synthesis of A1-15 and A1-16 of the above chemical formula A1.

[Example A-1]

[Example A-2]

The following examples are examples of the scheme of SM2 used in the synthesis of A2-18 and 2-19 of the above chemical formula A2.

[Example B-1]

[Example B-2]

<Manufacturing Example 6> Synthesis of Chemical Formula B1 or B2

In the above reaction formula,

R ₉ , R ₁₀ and Ar ₁ are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

n is an integer from 0 to 3, m is an integer from 0 to 4,

y is the number of deuterium,

R ₁ to R ₈ , and R' are each independently deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; or a substituted or unsubstituted aryl group.

After dissolving SM1 (chemical formula A, 1eq) in tetrahydrofuran (excess), the temperature was lowered to 0℃ and after the temperature was stabilized, N-bromosuccinimide (1eq) dissolved in dimethylformamide (3.5 times compared to NBS) was added dropwise. After the reaction was warmed to room temperature and stirred for 1 hour, 1N HCl (excess) was added to terminate the reaction. After completion of the reaction, the layers were separated to remove the solvent and then recrystallized with chloroform and ethyl acetate to produce the chemical formula B1 or B2.

In the synthesis method of the above chemical formula B1 or B2, B1-1 to B1-16 of Table 11 below were synthesized and B2-1 to B2-19 of Table 12 below were synthesized in the same manner, except that SM1 and SM2 were changed as shown in Tables 11 and 12 below.

[Table 11]

[Table 12]

<Manufacturing Example 7> Synthesis of chemical formulas P1 to P4

In the above reaction formula, X ₁ and X ₂ are each independently O or S,

R ₉ is hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

m is an integer from 0 to 6,

x, y and z are the number of deuterium atoms respectively,

R ₂₀₁ to R ₂₀₅ are the same as or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

R ₁ to R ₈ , and R' are each independently deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; or a substituted or unsubstituted aryl group.

After adding SM1 (chemical formula B, 1 eq) and SM2 (1.1 eq) to tetrahydrofuran (excess), 2 M potassium carbonate aqueous solution (30 volume ratio with respect to THF) was added, and tetrakistriphenyl-phosphinopalladium (2 mol%) was added, and the mixture was heated and stirred at 85°C for 10 hours. After lowering the temperature to room temperature and terminating the reaction, the potassium carbonate aqueous solution was removed, the layers were separated, and crystallization was performed with chloroform and ethyl acetate to prepare the chemical formulas P1 to P4 (compounds 1 to 38).

In the synthetic methods of the above chemical formulas P1 to P4, compounds 1 to 38 of Table 13 below were synthesized by the same method, except that SM1 and SM2 were changed as shown in Table 13 below.

[Table 13]

Compounds 1 to 38 of the above Table 13 are the final synthesized compounds, and starting material 1 (SM 1) or starting material 2 (SM 2) was used by substituting deuterium at the correct position from the synthesis of the intermediate according to the contents of this specification.

It was verified that the compound can be accurately designed and synthesized by accurately introducing deuterium into the anthracene skeleton using the above method and substituting additional deuterium at the exact positions of the aryl unit substituted at the 9th position (dibenzofuran unit) and 10th position (phenyl, biphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, terphenyl, etc.) of anthracene.

<Example 1> Manufacturing of organic light-emitting device

The substrate on which ITO/Ag/ITO was deposited as 70Å/1,000Å/70Å as an anode was cut into 50 mm x 50 mm x 0.5 mm sizes, placed in distilled water containing a dispersant, and ultrasonically cleaned. The detergent used was a product of Fischer Co., and the distilled water used was distilled water that had been filtered a second time through a filter of Millipore Co. 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 in the order of isopropyl alcohol, acetone, and methanol solvents, and then dried.

On the anode thus prepared, HI-1 was vacuum-deposited with a thickness of 50Å to form a hole injection layer, and HT1, a material that transports holes, was vacuum-deposited with a thickness of 1,150Å to form a hole transport layer. Next, a hole control layer was formed using EB1 (150Å), and then the host compound 1 synthesized above and dopant BD1 (2 wt%) were vacuum-deposited with a thickness of 360Å to form a light-emitting layer. After that, ET1 was deposited with a thickness of 50Å to form an electron control layer, and compounds ET2 and Liq were mixed in a ratio of 7:3 to form an electron transport layer with a thickness of 250Å. Magnesium and lithium fluoride (LiF) were sequentially deposited with a thickness of 50Å as an electron injection layer, after which 200Å of magnesium and silver (1:4) was formed as a cathode, and then 600Å of CP1 was deposited to complete the organic light-emitting device. In the above process, the deposition rate of organic matter was maintained at 1Å/sec.

The experimental results of examples 1 to 45 and comparative examples 1 to 10 of organic light-emitting devices manufactured using the above-described synthesized compounds 1 to 38 as host materials of the light-emitting layer and BD1 or BD2 as dopant materials of the light-emitting layer are shown in Table 14 below.

[Table 14]

The compound according to one embodiment of the present application relates to a blue fluorescent host in which dibenzofuran and dibenzothiophene are applied as a linker between anthracene and benzofuran and benzothiophene bonds, and it was intended to improve the performance of blue organic electroluminescent devices, particularly, the lifespan improvement, which has been shown to be a chronic difficulty, through specific deuteration of anthracene derivatives. In addition, it was intended to clearly confirm whether the performance was improved through the introduction of a substituent and deuteration of the relevant part compared to the prior art and the difference in the improvement of the present application, which could be confirmed through the above Examples 1 to 45.

Compounds 1 to 38 applied to the organic light-emitting devices of Examples 1 to 45 above were synthesized in which the hydrogen of the anthracene skeleton consists solely of deuterium and additional deuterium was substituted for the substituents at positions 9 and 10, depending on each compound. When the hydrogen of the anthracene skeleton is substituted with deuterium, it can be confirmed from the total deuterium substitution rate (%) that the deuterium substitution rate is between 20% and 100% depending on the molecular weight of the compound or the size of the substituent. In addition, the stability of the blue organic electroluminescent device can be improved through the increase in lifespan due to deuterium substitution compared to the prior art, and the improvement of voltage and efficiency through the introduction of the substituent.

In the above Examples 39 to 45, the results of the devices were confirmed by representatively changing only the blue dopant (BD1 -> BD2) for several compounds among Examples 1 to 38. As shown in the above results, the overall tendency for voltage and efficiency increase can be seen as the influence of the blue fluorescent dopant, and the results of these devices also confirmed that the lifespan was maintained above a certain level, thereby confirming that the increase in lifespan through deuteration of the anthracene blue host was maintained even when the dopant was changed.

The above comparative example 1 is a deuterium-free compound of an anthracene blue host of the aryl series, and it can be confirmed that it has a significantly higher voltage than the device of the anthracene blue host into which dibenzofuran is introduced.

The above Comparative Example 2 is the result of a device in which a compound having a skeleton in which anthracene is directly bonded to the carbon in the 3-position of benzofuran is introduced as a blue fluorescent host. It was confirmed that there was almost no advantage in the driving voltage compared to Comparative Example 1, which is an aryl series comparative example, when benzofuran was directly bonded, and it also showed a result with slightly insufficient efficiency in terms of the overall carrier balance. In addition, although deuterium was introduced by substituting it for phenyl, which is a substituent at position 10 of anthracene, not anthracene, it was found that the lifespan was considerably low. This can be judged to be due to the combined effects of the fact that deuterium was not substituted for anthracene, which is the main factor in the stability of the compound, and the poor lifespan characteristics of the compound itself, and this was compared with Comparative Examples 3 to 7 below.

The above Comparative Example 3 is the result of a device having a skeleton structure in which dibenzofuran was introduced, but was directly bonded to the benzofuran 3-carbon as a substituent of the benzofuran 2-carbon, not as a linker. Unlike the Comparative Examples 1 and 2, a heteroaryl group such as dibenzofuran, not an aryl group such as phenyl, was introduced, but since there was no advantage in the operating voltage, it was confirmed that the form in which benzofuran is directly bonded to anthracene did not bring out the voltage lowering effect of the heteroaryl unit. In addition, the lifespan of the structure in which phenyl-D5 was identically substituted at the 10-position of anthracene, as in the Comparative Example 1, can be confirmed to have the same lifespan characteristics as the Comparative Example 1 for the same reason.

The above Comparative Example 4 is the result of a device in which a compound having a skeleton in which anthracene is directly bonded to the carbon in the 2-direction of benzofuran is introduced as a blue fluorescent host, and compared to Comparative Example 2 (a skeleton in which anthracene is directly bonded to the carbon in the 2-direction of benzofuran), a slight decrease in the operating voltage is observed due to the characteristics of the compound, but on the contrary, a slight decrease in the efficiency is observed. In addition, deuterium is introduced to phenyl-D5 at position 10 of anthracene like in the compound of Comparative Example 2, and additionally, deuterium is introduced to all anthracene, and it can be confirmed that this has excellent lifespan characteristics compared to Comparative Example 2. However, since the characteristics of the device are inferior due to the characteristics of the compound, even though the deuterium substitution rate (%) is similar to that of the compound according to an exemplary embodiment of the present specification and deuterium is substituted in the anthracene nucleus, it can be confirmed that the compound according to an exemplary embodiment of the present specification has excellent characteristics as a blue fluorescent host.

The above Comparative Example 5 also has a high deuterium substitution rate of 67% similar to Comparative Example 4 and a structure in which deuterium of the anthracene nucleus is substituted, but despite a considerably high lifespan, it shows lower lifespan characteristics compared to the compound according to one embodiment of the present specification, and is understood to have the same tendency as Comparative Example 4.

The above Comparative Examples 6 and 7 are similar to the present application in that they are skeletons using a dibenzofuran unit as a linker, and show lower operating voltage and efficiency than Comparative Examples 1 to 5, but unlike Comparative Examples 2 and 3, deuterium is not introduced into the anthracene nucleus, but a phenyl-D5 unit is introduced. Accordingly, although some of the compounds of the above Examples 1 to 45 have similar deuterium substitution rates (%), the deviation in lifespan shows a significant gap, indicating that the position of deuterium introduction is important.

As shown in the above results, the benzofuran-anthracene derivative using the dibenzofuran unit of the present application as a linker exhibits excellent characteristics in terms of driving voltage, and exhibits excellent stability and balance of the device that have not been seen before due to various substitution rates of deuterium and introduction of deuterium into the anthracene nucleus.

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

Claims (22)

A compound of the following chemical formula 1:
[Chemical Formula 1]

In the above chemical formula 1,
One of R ₁ to R ₁₀ is represented by the following chemical formula 1-A, and the other is a substituted or unsubstituted aryl group,
The remainder of R ₁ to R ₁₀ are the same as or different from each other, and each independently represents deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; or a substituted or unsubstituted aryl group,
[Chemical Formula 1-A]

In the above chemical formula 1-A,
X ₁ is O or S,
One of R ₁₀₁ to R ₁₀₈ is a moiety bonded to chemical formula 1, and the other is represented by the following chemical formula 1-B,
The remainder of R ₁₀₁ to R ₁₀₈ are the same as or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,
[Chemical Formula 1-B]

In the above chemical formula 1-B,
X ₂ is O or S,
R ₂₀₁ to R ₂₀₅ are the same as or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,
* is a part that is combined with chemical formula 1-A,
However, when R ₁₀₄ of the above chemical formula 1-A is a part bonded to chemical formula 1, R ₁₀₁ , R ₁₀₃ , R ₁₀₅ , R ₁₀₆ , R ₁₀₇ or R ₁₀₈ is represented by chemical formula 1-B; when R ₁₀₅ of the above chemical formula 1-A is a part bonded to chemical formula 1, R ₁₀₁ , R ₁₀₂ , R ₁₀₃ , R ₁₀₄ , R ₁₀₆ or R ₁₀₈ is represented by chemical formula 1-B. delete delete In claim 1, R ₉ of the chemical formula 1 is represented by chemical formula 1-A,
R ₁₀ is an aryl group unsubstituted or substituted with at least one of deuterium and aryl groups; or an aryl group in which an aliphatic hydrocarbon ring is condensed,
A compound wherein R ₁ to R ₈ are each independently deuterium; or a substituted or unsubstituted aryl group. In claim 4, a compound wherein R ₁₀ in the chemical formula 1 is a phenyl group unsubstituted or substituted with at least one of a deuterium atom and an aryl group; a biphenyl group unsubstituted or substituted with a deuterium atom; a terphenyl group unsubstituted or substituted with a deuterium atom; a naphthyl group unsubstituted or substituted with at least one of a deuterium atom and an aryl group; a phenanthrene group unsubstituted or substituted with at least one of a deuterium atom and an aryl group; or a triphenylene group unsubstituted or substituted with at least one of a deuterium atom and an aryl group. In claim 1, R ₇ of the chemical formula 1 is represented by chemical formula 1-A,
R ₉ and R ₁₀ are each independently an aryl group unsubstituted or substituted with at least one of deuterium and aryl groups; or an aryl group condensed with an aliphatic hydrocarbon ring,
A compound wherein R ₁ to R ₆ and R ₈ are all deuterium. A compound according to claim 1, wherein among R ₁₀₁ to R ₁₀₈ of the chemical formula 1-A, the remainder, excluding the part bonded to chemical formula 1 and the part represented by chemical formula 1-B, are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. A compound according to claim 1, wherein the compound has a deuterium substitution rate of 1% to 100%. A compound according to claim 1, wherein the compound has a deuterium substitution rate of 40% to 99%. A compound according to claim 1, wherein the band gap energy of the compound is 2.9 eV or more. In claim 1, the chemical formula 1 is a compound selected from the following compounds:










An organic light-emitting device comprising a first electrode; a second electrode; and at least one organic layer provided between the first electrode and the second electrode,
An organic light-emitting device, wherein at least one of the organic layers comprises a compound according to any one of claims 1 and 4 to 11. An organic light-emitting device according to claim 12, wherein the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound as a host for the light-emitting layer. An organic light-emitting device according to claim 13, wherein the light-emitting layer further comprises a dopant, and the dopant comprises a fluorescent dopant. An organic light-emitting device according to claim 14, wherein the fluorescent dopant comprises at least one selected from a pyrene-based compound and a non-pyrene-based compound. An organic light-emitting device according to claim 15, wherein the non-pyrene-based compound includes a boron-based compound. An organic light-emitting device according to claim 13, wherein the host of the light-emitting layer is of two or more types. In claim 17, the two or more hosts include at least one first anthracene derivative containing deuterium, and at least one second anthracene derivative not containing deuterium.
An organic light-emitting device, wherein either the first anthracene derivative or the second anthracene derivative is the compound. In claim 17, the two or more hosts include two or more first anthracene derivatives containing deuterium,
An organic light-emitting device, wherein either one of the two first anthracene derivatives is the compound. An organic light-emitting device according to claim 17, wherein the light-emitting layer is a single layer in which two or more types of hosts are mixed. In claim 17, the light-emitting layer is a laminated structure including two or more light-emitting layers,
An organic light-emitting device wherein each of the two or more light-emitting layers contains different hosts. An organic light-emitting device according to claim 12, wherein the organic light-emitting device is a blue organic light-emitting device having a maximum emission wavelength (λ _max ) of an emission spectrum of 400 nm to 470 nm.