KR102412786B1 - Compound, coating composition comprising the same, and organic light emitting device using the same - Google Patents

Abstract

The present invention provides a compound represented by Formula 1, a coating composition comprising the same, and an organic light emitting device using the same.

Description

A compound, a coating composition comprising the same, and an organic light emitting device using the same

The present invention relates to a compound, a coating composition comprising the same, and an organic light emitting device comprising the same.

This application claims the benefit of the filing date of Korean Patent Application No. 10-2019-0085898 filed with the Korean Intellectual Property Office on July 16, 2019, the entire contents of which are incorporated herein by reference.

In general, the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material. The organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, and excellent luminance, driving voltage, and response speed characteristics, and thus many studies are being conducted.

An organic light emitting device generally has a structure including an anode and a cathode and an organic material layer between the anode and the cathode. The organic material layer is often made of a multi-layer structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, It may be made of an electron injection layer, etc. In the structure of the organic light emitting device, when a voltage is applied between the two electrodes, holes are injected into the organic material layer from the anode and electrons from the cathode are injected into the organic material layer. When the injected holes and electrons meet, excitons are formed, and the excitons When it falls back to the ground state, it lights up.

The development of new materials for organic materials used in organic light emitting devices as described above is continuously required.

Meanwhile, in recent years, organic light emitting devices using a solution process, particularly an inkjet process, have been developed instead of the conventional deposition process in order to reduce process costs. In the early days, all organic light emitting device layers were coated with a solution process to develop an organic light emitting device, but the current technology has limitations. Therefore, only HIL, HTL, and EML are processed in the solution process in the regular structure, and subsequent processes are performed using the conventional deposition process. A hybrid process using

Accordingly, the present invention provides a material for a novel organic light emitting device that can be used in an organic light emitting device and can be used in a solution process at the same time.

Korean Patent Publication No. 10-2000-0051826

The present invention relates to a compound, a coating composition comprising the same, and an organic light emitting device comprising the same.

The present invention provides a compound represented by the following formula (1):

[Formula 1]

In Formula 1,

X ₁ and X ₂ are each independently N(R ₃ ), O, or S,

each Y is independently CH, or N;

R ₁ , R ₂ and R ₃ are each independently hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted C _1-60 alkyl group; a substituted or unsubstituted C _1-60 alkoxy group; a substituted or unsubstituted C _2-60 alkenyl group; a substituted or unsubstituted C _2-60 alkynyl group; a substituted or unsubstituted C _3-60 cycloalkyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted C _6-60 aryl group; A C _2-60 heteroaryl group comprising any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S; a substituted or unsubstituted tri(C _1-60 alkyl)silyl group; Or a substituted or unsubstituted tri (C _6-60 aryl) silyl group,

n1 is each independently an integer of 1 to 3,

n2 is each independently an integer of 1 to 4,

When Y is all CH, at least one of X ₁ and X ₂ is N(R ₃ ) or S.

The present application provides a coating composition comprising the above-described compound. In addition, the present invention, the first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound represented by Formula 1 above; to provide.

The compound represented by Formula 1 described above can be used as a material for an organic material layer of an organic light emitting device, and can also be used in a solution process, and can improve efficiency, low driving voltage and/or lifespan characteristics in an organic light emitting device. have.

The compound of Formula 1 has a structure of a trimer including three structures of a heterocyclic ring containing boron, and is more chemically structurally stable than a compound of a structure containing one or two structures of a heterocyclic structure containing boron. Thereby, there is an excellent effect in terms of lifespan.

1 and 2 show examples of organic light emitting devices.

Hereinafter, it will be described in more detail to help the understanding of the present invention.

The present specification provides a compound represented by Formula 1 above.

In the present specification, when a member is said to be located “on” another member, this includes not only a case in which a member is in contact with another member but also a case in which another member is present between the two members.

In the present specification, when a part "includes" a certain component, it means that other components may be further included, rather than excluding other components, unless otherwise stated.

Throughout this specification, the term "combination of these" included in the expression of the Markush form means one or more mixtures or combinations selected from the group consisting of the components described in the expression of the Markush form, and the components It is meant to include one or more selected from the group consisting of.

(Definition of Terms)

또는

는 다른 치환기에 연결되는 결합을 의미한다.In this specification,

or

means a bond connected to another substituent.

As used herein, the term "substituted or unsubstituted" refers to deuterium; halogen group; cyano group; nitro group; hydroxyl group; carbonyl group; ester group; imid; amino group; a phosphine oxide group; alkoxy group; aryloxy group; alkyl thiooxy group; arylthioxy group; an alkyl sulfoxy group; arylsulfoxy group; silyl group; boron group; an alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; aralkenyl group; an alkylaryl group; an alkylamine group; an aralkylamine group; heteroarylamine group; arylamine group; an arylphosphine group; or N, O, and S atoms, which is substituted or unsubstituted with one or more substituents selected from the group consisting of heteroaryl containing one or more . For example, "a substituent in which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which two phenyl groups are connected.

In the present specification, the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like. However, the present invention is not limited thereto.

In the present specification, examples of the halogen group 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 40. According to an exemplary embodiment, the number of carbon atoms in the alkyl group is 1 to 20. According to another exemplary embodiment, the number of carbon atoms in the alkyl group is 1 to 10. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group 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, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like, but are not limited thereto.

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 40. According to an exemplary embodiment, the carbon number of the alkenyl group is 2 to 20. According to another exemplary embodiment, the carbon number of the alkenyl group is 2 to 10. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include 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 group, styrenyl group, and the like, but are not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, 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, and the like, but is not limited thereto.

In the present specification, the amine group is -NH ₂ ; monoalkylamine group; dialkylamine group; N-alkylarylamine group; monoarylamine group; diarylamine group; N-aryl heteroarylamine group; It may be selected from the group consisting of an N-alkylheteroarylamine group, a monoheteroarylamine group, and a diheteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, and a 9-methyl-anthracenylamine group. , diphenylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group; N-phenylnaphthylamine group; N-biphenylnaphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; N-biphenylphenanthrenylamine group; N-phenylfluorenylamine group; N-phenylterphenylamine group; N-phenanthrenylfluorenylamine group; N-biphenylfluorenylamine group and the like, but is not limited thereto.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 30. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 20. The aryl group may be a monocyclic aryl group, such as a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, and the like, but is not limited thereto.

등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. When the fluorenyl group is substituted,

etc. can be However, the present invention is not limited thereto.

In the present specification, heteroaryl is a heteroaryl containing at least one of O, N, Si and S as a heterogeneous element, and the number of carbon atoms is not particularly limited, but is preferably from 2 to 60 carbon atoms. Examples of heteroaryl include xanthene, thioxanthen, thiophene, furan, pyrrole, imidazole, thiazole, oxazole, oxadiazole, triazole, pyridyl, bipyridyl, Pyrimidyl group, triazine group, acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino Pyrazinyl group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group ( phenanthroline), an isoxazolyl group, a thiadiazolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but are not limited thereto.

In the present specification, the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, arylamine group, and arylsilyl group is the same as the above-described aryl group. In the present specification, the alkyl group among the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the example of the above-described alkyl group.

In the present specification, as for heteroaryl among heteroarylamines, the description regarding heteroaryl described above may be applied.

In the present specification, the alkenyl group among the aralkenyl groups is the same as the above-described examples of the alkenyl group.

In the present specification, the description of the above-described aryl group may be applied, except that arylene is a divalent group.

In the present specification, the description of the above-described heteroaryl may be applied, except that heteroarylene is a divalent group. In the present specification, the hydrocarbon ring is not a monovalent group, and the description of the above-described aryl group or cycloalkyl group may be applied, except that it is formed by combining two substituents.

In the present specification, the heterocyclic group is not a monovalent group, and the description regarding heteroaryl described above may be applied, except that it is formed by combining two substituents.

(compound)

In an exemplary embodiment of the present specification, when Y is all CH, at least one of X ₁ and X ₂ is N(R ₃ ) or S.

In the exemplary embodiment of the present specification, when Y is all CH, at least one of X ₁ and X ₂ is N(R ₃ ).

In the exemplary embodiment of the present specification, when Y is all CH, X ₁ and X ₂ are the same as or different from each other, and each independently N(R ₃ ) or S.

In the exemplary embodiment of the present specification, when Y is all CH, X ₁ and X ₂ are N(R ₃ ).

In an exemplary embodiment of the present specification, Y is all N.

In the exemplary embodiment of the present specification, at least one of Y is N, and the rest is CH.

In an exemplary embodiment of the present specification, one of Y is N, and the other is CH.

In the exemplary embodiment of the present specification, at least two of Y are N, and the rest are CH.

In an exemplary embodiment of the present specification, two of Y are N, and the remainder is CH.

In an exemplary embodiment of the present specification, the X ₁ and X ₂ may be N(R ₃ ), O, or S, but the compound in the case of NR″ is preferred.

In an exemplary embodiment of the present specification, the X ₁ and X ₂ are N(R ₃ ), and R ₃ is hydrogen; heavy hydrogen; a substituted or unsubstituted C _6-60 aryl group; Or a C _2-60 heteroaryl group comprising any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S.

In an exemplary embodiment of the present specification, X ₁ and X ₂ are N(R ₃ ), and R ₃ is a substituted or unsubstituted C _6-60 aryl group; Or a C _2-60 heteroaryl group comprising any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S.

In an exemplary embodiment of the present specification, the X ₁ and X ₂ are N(R ₃ ), and R ₃ is hydrogen; heavy hydrogen; a substituted or unsubstituted C6-C20 aryl group; or a C 2 to C 20 heteroaryl group including any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S.

In an exemplary embodiment of the present specification, the X ₁ and X ₂ are N(R ₃ ), wherein R ₃ is a substituted or unsubstituted C 6 to C 20 aryl group; or a C 2 to C 20 heteroaryl group including any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S.

In an exemplary embodiment of the present specification, the X ₁ and X ₂ are N(R ₃ ), and R ₃ is hydrogen; heavy hydrogen; C _6-60 aryl group unsubstituted or substituted with a substituent selected from the group consisting of an alkyl group, an alkoxy group, a silyl group, an amine group, an aryl group, and a heteroaryl group; or an alkyl group, an alkoxy group, a silyl group, an amine group, an aryl group, and any one or more heteroatoms selected from the group consisting of N, O and S unsubstituted or substituted with a substituent selected from the group consisting of a heteroaryl group is a C _2-60 heteroaryl group.

In an exemplary embodiment of the present specification, X ₁ and X ₂ are N(R ₃ ), and R ₃ is selected from the group consisting of an alkyl group, an alkoxy group, a silyl group, an amine group, an aryl group, and a heteroaryl group. C _6-60 aryl group unsubstituted or substituted with a substituent; or an alkyl group, an alkoxy group, a silyl group, an amine group, an aryl group, and any one or more heteroatoms selected from the group consisting of N, O and S unsubstituted or substituted with a substituent selected from the group consisting of a heteroaryl group is a C _2-60 heteroaryl group.

In an exemplary embodiment of the present specification, the X ₁ and X ₂ are N(R ₃ ), and R ₃ is hydrogen; heavy hydrogen; or an amine group substituted with an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a silyl group substituted with an alkyl group having 1 to 10 carbon atoms, an amine group substituted with an aryl group having 6 to 20 carbon atoms, or N, O and It is an aryl group having 6 to 20 carbon atoms that is unsubstituted or substituted with a heteroaryl group containing one or more heteroatoms selected from the group consisting of S.

In an exemplary embodiment of the present specification, the X ₁ and X ₂ are N(R ₃ ), and R ₃ is an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or an alkyl group having 1 to 10 carbon atoms. silyl group, an amine group substituted with an aryl group having 6 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms unsubstituted or substituted with a heteroaryl group having 2 to 20 carbon atoms.

In an exemplary embodiment of the present specification, the X ₁ and X ₂ are N(R ₃ ), and R ₃ is an alkyl group having 1 to 10 carbon atoms, a silyl group substituted with an alkyl group having 1 to 10 carbon atoms, and 6 to 20 carbon atoms. an amine group substituted with an aryl group of, or an aryl group having 6 to 20 carbon atoms substituted with a heteroaryl group having 2 to 20 carbon atoms.

In an exemplary embodiment of the present specification, the X ₁ and X ₂ are N(R ₃ ), and R ₃ is hydrogen; heavy hydrogen; or an alkyl group, an alkoxy group, a silyl group substituted with an alkyl group, an amine group substituted with an aryl group, or an aryl group substituted with a heteroaryl group.

In an exemplary embodiment of the present specification, X ₁ and X ₂ are N(R ₃ ), wherein R ₃ is hydrogen; heavy hydrogen; or a substituted or unsubstituted phenyl group.

In an exemplary embodiment of the present specification, X ₁ and X ₂ are N(R ₃ ), and R ₃ is a substituted or unsubstituted phenyl group.

In an exemplary embodiment of the present specification, the X ₁ and X ₂ are N(R ₃ ), and R ₃ is hydrogen; heavy hydrogen; or a substituted phenyl group.

In an exemplary embodiment of the present specification, X ₁ and X ₂ are N(R ₃ ), and R ₃ is a substituted phenyl group.

In an exemplary embodiment of the present specification, X ₁ and X ₂ are N(R ₃ ), wherein R ₃ is an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, substituted with an alkyl group having 1 to 10 carbon atoms a phenyl group unsubstituted or substituted with an amine group substituted with a silyl group, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 2 to 20 carbon atoms; Or substituted with an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a silyl group substituted with an alkyl group having 1 to 10 carbon atoms, an amine group substituted with an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 2 to 20 carbon atoms or an unsubstituted or biphenyl group.

In an exemplary embodiment of the present specification, the X ₁ and X ₂ are N(R ₃ ), and R ₃ is an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or an alkyl group having 1 to 10 carbon atoms. a silyl group, an amine group substituted with an aryl group having 6 to 20 carbon atoms, or a phenyl group substituted with a heteroaryl group having 2 to 20 carbon atoms; Or substituted with an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a silyl group substituted with an alkyl group having 1 to 10 carbon atoms, an amine group substituted with an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 2 to 20 carbon atoms is a biphenyl group.

In an exemplary embodiment of the present specification, the X ₁ and X ₂ are N(R ₃ ), and R ₃ is hydrogen; heavy hydrogen; or a methyl group, an ethyl group, a propyl group, a butyl group, a methoxy group, a trimethylsilyl group, a tripropylsilyl group, a diphenylamine group, a carbazole group, a phenylcarbazole group, a dibenzofuran group, a dibenzothiophene group, and a phenoxazine group It is a phenyl group substituted with one or more substituents selected from the group consisting of.

In an exemplary embodiment of the present specification, the X ₁ and X ₂ are N(R ₃ ), and R ₃ is hydrogen; heavy hydrogen; or a methyl group, a tert-butyl group, a methoxy group, a trimethylsilyl group, a triisopropylsilyl group, a diphenylamine group, a carbazole group, a phenylcarbazole group, a dibenzofuran group, a dibenzothiophene group, and a phenoxazine group. It is a phenyl group substituted with one or more substituents selected from.

In an exemplary embodiment of the present specification, X ₁ and X ₂ are N(R ₃ ), and R ₃ is a methyl group, an ethyl group, a propyl group, a butyl group, a methoxy group, a trimethylsilyl group, a tripropylsilyl group, a di It is a phenyl group substituted with one or more substituents selected from the group consisting of a phenylamine group, a carbazole group, a phenylcarbazole group, a dibenzofuran group, a dibenzothiophene group, and a phenoxazine group.

In an exemplary embodiment of the present specification, X ₁ and X ₂ are N(R ₃ ), and R ₃ is a methyl group, tert-butyl group, methoxy group, trimethylsilyl group, triisopropylsilyl group, diphenylamine It is a phenyl group substituted with one or more substituents selected from the group consisting of a group, a carbazole group, a phenylcarbazole group, a dibenzofuran group, a dibenzothiophene group, and a phenoxazine group.

In an exemplary embodiment of the present specification, R ₁ and R ₂ are the same as or different from each other and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C _1-60 alkyl group; a substituted or unsubstituted tri(C _1-60 alkyl)silyl group; a substituted or unsubstituted tri(C _6-60 aryl)silyl group; a substituted or unsubstituted C _6-60 aryl group; Or a C _2-60 heteroaryl group comprising any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S.

In an exemplary embodiment of the present specification, R ₁ and R ₂ are the same as or different from each other and each independently hydrogen; heavy hydrogen; C _1-60 alkyl group; a tri(C _{1-60 alkyl} )silyl group substituted or unsubstituted with an alkyl group; a tri(C _6-60 aryl)silyl group unsubstituted or substituted with an alkyl group; C _6-60 aryl group unsubstituted or substituted with an alkyl group, a silyl group, an amine group, or a heterocyclic group; or a C _2-60 heteroaryl group including any one or more heteroatoms selected from the group consisting of N, O and S substituted or unsubstituted with an aryl group.

In an exemplary embodiment of the present specification, R ₁ and R ₂ are the same as or different from each other and each independently hydrogen; heavy hydrogen; an alkyl group having 1 to 10 carbon atoms; a tri(C _1-60 alkyl)silyl group substituted with an alkyl group having 1 to 10 carbon atoms; a tri(C _6-60 aryl)silyl group substituted with an alkyl group having 1 to 10 carbon atoms; an amine group substituted with an aryl group having 6 to 20 carbon atoms; a substituted or unsubstituted C6-C20 aryl group; Or a C 2 to C 20 heteroaryl group including any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S,

The aryl group and the heteroaryl group may include an alkyl group having 1 to 10 carbon atoms; a silyl group substituted with an alkyl group having 1 to 10 carbon atoms; an amine group substituted with an aryl group having 6 to 20 carbon atoms; an aryl group having 6 to 20 carbon atoms; And it may be unsubstituted or substituted with one or more substituents selected from the group consisting of a heteroaryl group having 2 to 20 carbon atoms.

In an exemplary embodiment of the present specification, R ₁ and R ₂ are the same as or different from each other and each independently hydrogen; heavy hydrogen; methyl group; ethyl group; Profile group; butyl group; trimethylsilyl group; a carbazole group; phenoxazine; or a phenyl group substituted with a diphenylamine group.

In an exemplary embodiment of the present specification, R ₁ and R ₂ are the same as or different from each other and each independently hydrogen; heavy hydrogen; methyl group; tert-butyl group; trimethylsilyl group; a carbazole group; phenoxazine; or a phenyl group substituted with a diphenylamine group.

In an exemplary embodiment of the present specification, at least one of R ₁ and R ₂ is a substituted or unsubstituted C _1-60 alkyl group; a substituted or unsubstituted tri(C _1-60 alkyl)silyl group; Or a substituted or unsubstituted tri (C _6-60 aryl) silyl group; a substituted or unsubstituted C _6-60 aryl group; Or a C _2-60 heteroaryl group comprising any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S.

In an exemplary embodiment of the present specification, at least one of R ₁ and R ₂ is an alkyl group having 1 to 10 carbon atoms; a tri(C _1-60 alkyl)silyl group substituted with an alkyl group having 1 to 10 carbon atoms; a tri(C _6-60 aryl)silyl group substituted with an alkyl group having 1 to 10 carbon atoms; an aryl group having 6 to 20 carbon atoms substituted with an amine group substituted with an aryl group having 6 to 20 carbon atoms; or a heteroaryl group having 2 to 20 carbon atoms including any one or more heteroatoms selected from the group consisting of N, O and S.

In an exemplary embodiment of the present specification, at least one of R ₁ and R ₂ is a methyl group; tert-butyl group; trimethylsilyl group; a carbazole group; phenoxazine; or a phenyl group substituted with a diphenylamine group.

In an exemplary embodiment of the present specification, at least one of R ₁ and R ₂ is a substituted or unsubstituted C _1-60 alkyl group; a substituted or unsubstituted tri(C _1-60 alkyl)silyl group; Or a substituted or unsubstituted tri (C _6-60 aryl) silyl group; a substituted or unsubstituted C _6-60 aryl group; Or a C _2-60 heteroaryl group containing any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S, and the remainder is hydrogen.

In an exemplary embodiment of the present specification, at least one of R ₁ and R ₂ is an alkyl group having 1 to 10 carbon atoms; a tri(C _1-60 alkyl)silyl group substituted with an alkyl group having 1 to 10 carbon atoms; a tri(C _6-60 aryl)silyl group substituted with an alkyl group having 1 to 10 carbon atoms; an aryl group having 6 to 20 carbon atoms substituted with an amine group substituted with an aryl group having 6 to 20 carbon atoms; or a heteroaryl group having 2 to 20 carbon atoms including any one or more heteroatoms selected from the group consisting of N, O and S, and the remainder is hydrogen.

In an exemplary embodiment of the present specification, at least one of R ₁ and R ₂ is a methyl group; tert-butyl group; trimethylsilyl group; a carbazole group; phenoxazine; or a phenyl group substituted with a diphenylamine group, and the remainder is hydrogen.

In an exemplary embodiment of the present specification, Chemical Formula 1 may be represented by any one of Chemical Formulas 2 to 4 below.

[Formula 2]

[Formula 3]

[Formula 4]

In the following formulas 2 to 4,

Y, X ₁ X ₂ , R ₁ , R ₂ , n1 and n2 are as defined in Formula 1.

In the exemplary embodiment of the present specification, it is preferable that Chemical Formula 1 is Chemical Formula 2 or 4.

Preferably, X ₁ are identical to each other and X ₂ are identical to each other.

Preferably, Y are equal to each other.

Preferably, R ₁ and R ₂ are each independently hydrogen or a C _1-10 alkyl group.

Preferably, R ₁ and R ₂ are each independently hydrogen, a methyl group, or a tert-butyl group.

Preferably, each R ₃ is independently hydrogen or a phenyl group,

The phenyl group is unsubstituted or substituted with a C _1-10 alkyl group, a C _1-10 alkoxy group, a tri(C _1-10 alkyl)silyl group, a 9-phenyl-carbazolyl group, or a carbazol-9-yl group.

Preferably, each R ₃ is independently hydrogen or a phenyl group,

The phenyl group is unsubstituted; or a methyl group, a tert-butyl group, a methoxy group, a trimethylsilyl group, a tri(isopropyl)silyl group, a 9-phenyl-carbazolyl group, or a carbazol-9-yl group.

Representative examples of the compound represented by Formula 1 are as follows:

On the other hand, the present invention provides a method for preparing a compound represented by Formula 1 as shown in Scheme 1 below as an example:

[Scheme 1]

In Scheme 1, definitions other than X are the same as defined above, and X is halogen, more preferably chloro or bromo. The manufacturing method may be more specific in Preparation Examples to be described later.

(Coating composition)

The compound according to the present invention can form an organic layer of an organic light emitting device, particularly, a light emitting layer by a solution process. To this end, the present invention provides a coating composition comprising the above-described compound according to the present invention and a solvent.

In one embodiment of the present specification, a composition comprising the compound of Formula 1 is provided.

In one embodiment of the present specification, the composition including the compound is a coating composition for an organic light emitting device.

In one embodiment of the specification, the coating composition may be liquid. The "liquid phase" means a liquid state at room temperature and pressure.

The solvent is not particularly limited as long as it is a solvent capable of dissolving or dispersing the compound according to the present invention, and for example, chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, o - Chlorine solvents, such as dichlorobenzene; ether solvents such as tetrahydrofuran and dioxane; aromatic hydrocarbon solvents such as toluene, xylene, trimethylbenzene, and mesitylene; aliphatic hydrocarbon solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, and n-decane; Ketone solvents, such as acetone, methyl ethyl ketone, and cyclohexanone; ester solvents such as ethyl acetate, butyl acetate, and ethyl cellosolve acetate; Polyvalents such as ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, and 1,2-hexanediol alcohols and derivatives thereof; alcohol solvents such as methanol, ethanol, propanol, isopropanol and cyclohexanol; sulfoxide solvents such as dimethyl sulfoxide; and amide solvents such as N-methyl-2-pyrrolidone and N,N-dimethylformamide; benzoate solvents such as butylbenzoate and methyl-2-methoxybenzoate; tetralin; and solvents such as 3-phenoxy-toluene. In addition, the above-mentioned solvents may be used alone or as a mixture of two or more solvents.

In another embodiment, the boiling point of the solvent is preferably 40 °C to 250 °C, more preferably 60 °C to 230 °C, but is not limited thereto.

In another embodiment, the boiling point of the solvent is preferably 40 °C to 250 °C, more preferably 60 °C to 230 °C, but is not limited thereto.

In another exemplary embodiment, the viscosity of the single or mixed solvent is preferably 1 to 10 CP, more preferably 3 to 8 CP, but is not limited thereto.

In addition, the viscosity of the coating composition is preferably 1 cP to 10 cP, and coating is easy in the above range. In addition, the concentration of the polymer according to the present invention in the coating composition is 0.1 wt/v% to 20 wt/v%, more preferably 0.5 to 5 wt/v%, but is not limited thereto. In one embodiment of the present specification, the coating composition may further include one or more additives selected from the group consisting of a thermal polymerization initiator and a photopolymerization initiator.

Examples of the thermal polymerization initiator include methyl ethyl ketone peroxide, methyl isobutyl ketone peroxide, acetylacetone peroxide, methylcyclohexanone peroxide, cyclohexanone peroxide, isobutyryl peroxide, and 2,4-dichlorobenzoyl peroxide. Oxide, bis-3,5,5-trimethyl hexanoyl peroxide, lauryl peroxide, benzoyl peroxide, p-chlorobenzoyl peroxide, dicumylperoxide, 2,5-dimethyl-2,5-(t- Butyl oxy)-hexane, 1,3-bis(t-butyl peroxy-isopropyl) benzene, t-butyl cumyl peroxide, di-tbutyl peroxide, 2,5-dimethyl-2,5- (di-t-butyl peroxy) hexane-3, tris-(t-butyl peroxy) triazine, 1,1-dit-butyl peroxy-3,3,5-trimethyl cyclohexane, 1,1-di t-Butyl peroxycyclohexane, 2,2-di(t-butyl peroxy)butane, 4,4-di-t-butylpaoxyvaleric acid n-butyl ester, 2,2-bis(4 ,4-t-Butyl peroxycyclohexyl)propane, t-butylperoxyisobutylate, dit-butyl peroxyhexahydro terephthalate, t-butyl peroxy-3,5,5-trimethylhexaate, t -Peroxides such as butyl peroxybenzoate and dit-butyl peroxy trimethyl adipate, or azo-based compounds such as azobis isobutylnitrile, azobisdimethylvaleronitrile, and azobiscyclohexyl nitrile, but are not limited thereto .

Examples of the photopolymerization initiator include diethoxy acetophenone, 2,2-dimethoxy-1,2-diphenyl ethan-1-one, 1-hydroxy-cyclohexyl-phenyl-ketone, 4-(2-hydroxyethoxy) ) Phenyl- (2-hydroxy-2-propyl) ketone, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butanone-1,2-hydroxy-2-methyl-1- Phenyl propan-1-one, 2-methyl-2-morpholino (4-methyl thio phenyl) propan-1-one, 1-phenyl-1,2-propanedione-2- (o-ethoxycarbonyl) Acetophenone-based or ketal-based photopolymerization initiators such as oxime; Ether type photoinitiator, benzophenone type photoinitiator, such as benzophenone, 4-hydroxybenzophenone, 2-benzoyl naphthalene, 4-benzoyl biphenyl, 4-benzoyl phenyl ether, acrylated benzophenone, 1, 4- benzoylbenzene, etc. ,2-isopropylthioxanthone, 2-chlorothioxanthone, 2,4-dimethyl thioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, thioxanthone-based photopolymerization Examples of the initiator and other photopolymerization initiators include ethyl anthraquinone, 2,4,6-trimethylbenzoyl diphenyl phosphine oxide, 2,4,6-trimethylbenzoyl phenyl ethoxy phosphine oxide, bis(2,4,6-trimethylbenzoyl) ) phenyl phosphine oxide, bis (2,4-dimethoxy benzoyl) -2,4,4-trimethyl pentyl phosphine oxide, methyl phenyl glyceryl ester, 9, 10-phenanthrene, acridine-based compound; A triazine-type compound and an imidazole-type compound are mentioned. Moreover, what has a photoinitiator effect can also be used individually or in combination with the said photoinitiator. For example, triethanolamine, methyl diethanol amine, 4-dimethylamino ethyl benzoate, 4-dimethylamino benzoate isoamyl, benzoate (2-dimethylamino) ethyl, 4,4'-dimethylaminobenzophenone, etc., but, It does not limit this.

In addition, the present invention provides a method of forming a light emitting layer using the above-described coating composition. Specifically, on the positive electrode, or on the hole transport layer formed on the positive electrode, coating the coating composition according to the present invention as described above in a solution process; and heat-treating the coated coating composition.

The solution process uses the coating composition according to the present invention described above, and refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying method, roll coating, and the like, but is not limited thereto.

The heat treatment temperature in the heat treatment step is preferably 150 to 230 ℃. In addition, the heat treatment time is 1 minute to 3 hours, more preferably 10 minutes to 1 hour. In addition, the heat treatment is preferably performed in an inert gas atmosphere such as argon or nitrogen. In addition, the step of evaporating the solvent between the coating step and the heat treatment step may be further included.

(organic light emitting element)

The present specification also provides an organic light emitting device formed using the coating composition.

In one embodiment of the present specification, the first electrode; a second electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers is formed using a coating composition including the compound of Formula 1 above.

In one embodiment of the present specification, the first electrode; a second electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes a coating composition including the compound of Formula 1 or a cured product thereof.

In one embodiment of the present specification, the cured product of the coating composition is in a cured state by heat treatment or light treatment of the coating composition.

In addition, the present invention provides an organic light emitting device comprising the compound represented by Formula 1 above.

In one example, the present invention provides a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes a cured product of the compound according to the present invention. provides

The organic material layer of the organic light emitting device of the present application may have a single-layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked. For example, as a representative example of the organic light emitting device of the present invention, the organic light emitting device 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 injection and transport layer, etc. as an organic material layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.

For example, the structure of the organic light emitting device according to an exemplary embodiment of the present specification is illustrated in FIGS. 1 and 2 .

1 illustrates a structure of an organic light emitting device in which an anode 2 , a light emitting layer 3 , and a cathode 4 are sequentially stacked on a substrate 1 .

2, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron injection and transport layer 8 and a cathode 4 are sequentially stacked on a substrate 1 The structure of the light emitting device is illustrated.

In FIG. 2, the hole injection layer 5, the hole transport layer 6, or the light emitting layer 7 is formed using a coating composition including the compound represented by Formula 1, or the compound represented by Formula 1 is the hole It may be included in the injection layer, the hole transport layer, or the light emitting layer.

1 and 2 illustrate an organic light emitting device, but is not limited thereto.

In an exemplary embodiment of the present application, the organic material layer includes a light emitting layer, and the light emitting layer includes the coating composition or a cured product thereof.

In the exemplary embodiment of the present application, the light emitting layer is a blue light emitting layer.

In the exemplary embodiment of the present application, the maximum emission wavelength of the emission layer is 430 nm to 460 nm.

In the exemplary embodiment of the present application, the maximum absorption wavelength of the light emitting layer is 430 nm to 460 nm.

In an exemplary embodiment of the present application, the coating composition further comprises a host material,

The compound and the host material are included in a weight ratio of 1:1 to 1:200.

In an exemplary embodiment of the present application, the coating composition further comprises a host material,

The host material is represented by the following formula (A).

[Formula A]

In Formula A, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

L20 is a direct bond; Or a substituted or unsubstituted arylene group,

R100 is hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

r100 is an integer from 0 to 8, and when r100 is 2 or more, R100 is the same as or different from each other.

In an exemplary embodiment of the present application, Ar1 and Ar2 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with an aryl group; Or a heteroaryl group unsubstituted or substituted with an aryl group.

In an exemplary embodiment of the present application, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C 2 to C 20 heteroaryl group.

In an exemplary embodiment of the present application, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted anthracene group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group.

In an exemplary embodiment of the present application, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with an aryl group; a biphenyl group unsubstituted or substituted with an aryl group; a naphthyl group unsubstituted or substituted with an aryl group; an anthracene group unsubstituted or substituted with an aryl group; Or a dibenzofuran group unsubstituted or substituted with an aryl group.

In an exemplary embodiment of the present application, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a naphthyl group; a naphthyl group unsubstituted or substituted with a naphthyl group; an anthracene group unsubstituted or substituted with a naphthyl group; or a dibenzofuran group.

In an exemplary embodiment of the present application, Ar1 and Ar2 are the same as or different from each other, and each independently a 1-naphthyl group; 2-naphthyl group; an anthracene group substituted with a naphthyl group; or a dibenzofuran group.

In an exemplary embodiment of the present application, Ar1 and Ar2 are the same as or different from each other, and each independently represents a 1-naphthyl group or a 2-naphthyl group.

In an exemplary embodiment of the present application, L20 is a direct bond; phenylene group; or a divalent naphthyl group.

In an exemplary embodiment of the present application, L20 is a direct bond.

In an exemplary embodiment of the present application, R100 is hydrogen; a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

In an exemplary embodiment of the present application, R100 is hydrogen; an alkyl group; or an aryl group unsubstituted or substituted with an alkyl group.

In an exemplary embodiment of the present application, R100 is hydrogen; an alkyl group having 1 to 10 carbon atoms; or an aryl group having 6 to 20 carbon atoms which is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms.

In an exemplary embodiment of the present application, R100 is hydrogen; an alkyl group having 1 to 10 carbon atoms; or a phenyl group having 6 to 20 carbon atoms which is unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms.

In an exemplary embodiment of the present application, the compound of Formula A may be selected from the following structural formula.

In an exemplary embodiment of the present application, the organic material layer includes a hole injection layer or a hole transport layer.

In the exemplary embodiment of the present application, the organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer.

In an exemplary embodiment of the present application, the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the coating composition or a cured product thereof.

In an exemplary embodiment of the present application, the organic material layer includes a hole injection layer, a hole transport layer or a hole injection and transport layer, and the hole injection layer, the hole transport layer or the hole injection and transport layer includes the coating composition or a cured product thereof .

In an exemplary embodiment of the present application, the organic material layer includes an electron transport layer or an electron injection layer.

In an exemplary embodiment of the present application, the organic material layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer.

In an exemplary embodiment of the present application, the organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the coating composition or a cured product thereof. In an exemplary embodiment of the present application, the organic material layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer or the electron injection and transport layer includes the coating composition or a cured product thereof. .

The organic light emitting device of the present specification may be manufactured using materials and methods known in the art, except that at least one layer of the organic material layer is formed using a coating composition including the compound.

The organic light emitting device of the present specification includes a hole injection layer, a hole transport layer, a light emitting layer, and an electron injection and transport layer.

The organic light emitting device of the present specification includes a hole injection layer, a hole transport layer, a light emitting layer, and an electron injection and transport layer,

The hole injection layer, the hole transport layer, and the light emitting layer are formed through a solution process.

Also, the organic light emitting device according to the present invention may be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. Also, the organic light emitting device according to the present invention may be an inverted type organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.

The organic light emitting device according to the present invention may be manufactured using materials and methods known in the art, except for using the compound according to the present invention.

For example, the organic light emitting device according to the present invention may be manufactured by sequentially stacking an anode, an organic material layer, and a cathode on a substrate. At this time, by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or an alloy thereof is deposited on a substrate to form an anode And, after forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, it can be prepared by depositing a material that can be used as a cathode thereon.

In addition to this method, an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited thereto.

In one example, the first electrode is an anode, the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.

As the anode material, a material having a large work function is generally preferred so that holes can be smoothly injected into the organic material layer. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO ₂ :Sb; conductive compounds such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

The cathode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the anode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; and a multi-layered material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

The hole injection layer is a layer for injecting holes from the electrode, and as a hole injection material, it has the ability to transport holes, so it has a hole injection effect at the anode, an excellent hole injection effect on the light emitting layer or the light emitting material, and is produced in the light emitting layer A compound which prevents the movement of excitons to the electron injection layer or the electron injection material and is excellent in the ability to form a thin film is preferable. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based organic material. of organic substances, anthraquinones, polyaniline and polythiophene-based conductive compounds, and the like, but are not limited thereto.

In an exemplary embodiment of the present specification, the hole injection layer includes an ionic compound.

In an exemplary embodiment of the present specification, the hole injection layer includes a coating composition including an ionic compound or a cured product thereof.

In an exemplary embodiment of the present specification, the hole injection layer includes a coating composition including an ionic compound or a cured product thereof, and the ionic compound is included as a p doping material.

In the present specification, the p-doped material refers to a material that allows the host material to have p-semiconductor properties. The p-semiconductor property refers to the property of receiving or transporting holes at the highest occupied molecular orbital (HOMO) energy level, that is, the property of a material having high hole conductivity.

In an exemplary embodiment of the present specification, the hole injection layer includes a coating composition including an arylamine compound or a cured product thereof.

In an exemplary embodiment of the present specification, the hole injection layer includes a coating composition including an arylamine compound or a cured product thereof, and includes the arylamine compound as a host of the hole injection layer.

In an exemplary embodiment of the present specification, the hole injection layer includes an ionic compound and an arylamine compound in a weight ratio of 1: 1 to 1: 10.

In an exemplary embodiment of the present specification, the arylamine compound is a single molecule or a polymer.

In an exemplary embodiment of the present specification, the host of the hole injection layer further comprises a monomolecular or polymer arylamine compound.

In an exemplary embodiment of the present specification, the arylamine compound includes a curing group.

In the exemplary embodiment of the present specification, the host of the hole injection layer has a HOMO level of 4.8 eV to 5.8 eV.

The HOMO level of the present specification is measured using electrochemical cyclic voltammetry (CV). The onset potential (E _onset ) at which the oxidation of the host material starts is measured, and the potential of ferrocene (E _{1/2 ( Fc )} ) is measured under the same conditions. Set the potential of ferrocene as 4.8 eV compared to the vacuum energy level and calculate it using the following formula.

HOMO (eV) = 4.8 + (E _onset - E _{1/2 (Fc)} )

The compound of the arylamine group may form a cross-link to provide an organic material layer including a thinned structure. In this case, it is possible to prevent dissolution, morphological influence, or decomposition by the solvent deposited on the surface of the organic material layer formed using the coating composition.

The hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light emitting layer. The hole transport material is a material that can transport holes from the anode or the hole injection layer to the light emitting layer and transfer them to the light emitting layer. material is suitable. Specific examples include, but are not limited to, an arylamine-based organic material, a conductive compound, and a block copolymer having a conjugated portion and a non-conjugated portion together.

An electron blocking layer may be provided between the hole transport layer and the light emitting layer. For the electron blocking layer, a material known in the art may be used.

The light emitting layer may emit red, green, or blue light, and may be made of a phosphorescent material or a fluorescent material. The light emitting material is a material capable of emitting light in the visible ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene, rubrene, and the like, but is not limited thereto.

The emission layer may include a host material and a dopant material. The host material includes a condensed aromatic ring derivative or a heterocyclic compound containing compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

Examples of the dopant material include an aromatic amine derivative, a strylamine compound, a boron complex, a fluoranthene compound, and a metal complex. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, periflanthene, and the like, having an arylamino group. As the styrylamine compound, a substituted or unsubstituted As a compound in which at least one arylvinyl group is substituted in the arylamine, one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but is not limited thereto. In addition, examples of the metal complex include, but are not limited to, an iridium complex and a platinum complex.

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

The electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, and hole injection of excitons generated in the light emitting layer. A compound which prevents movement to a layer and is excellent in the ability to form a thin film is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc., derivatives thereof, metals complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

Examples of the metal complex compound 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-crezolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc. However, the present invention is not limited thereto.

The hole blocking layer is a layer that blocks the holes from reaching the cathode, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complex, and the like, but is not limited thereto.

The organic light emitting device according to the present invention may be a top emission type, a back emission type, or a double side emission type depending on the material used.

In addition, the compound according to the present invention may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.

The compound represented by Formula 1 and the preparation of an organic light emitting device including the same will be described in detail in Examples below. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto.

[ Example ]

production example 1: Preparation of compound 1

Step 1-1: Synthesis of intermediate compound 1-c

Compound 1-a (5.0 g, 1.0 eq.) and compound 1-b (3.3 eq.) were placed in a round bottom flask and dissolved in anhydrous tetrahydrofuran (THF) (0.3 M). K ₂ CO ₃ (3.3 eq.) dissolved in water was injected. Pd(PPh ₃ ) ₄ (9 mol%) was added dropwise under a bath temperature of 80 °C and stirred overnight. After the reaction, the organic layer was separated by washing with CH ₂ Cl ₂ /H ₂ O. Water was removed with MgSO ₄ and passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure and purified by column chromatography to prepare compound 1-c (8.0 g, 95% yield).

m/z [M+H] ⁺ C ₂₄ H ₂₂ N ₃ ⁺ 352.2

Step 1-2: Synthesis of intermediate compound 1-e

Compound 1-c (6.0 g, 1.0 eq.), compound 1-d (3.3 eq.) and NaO t -Bu (6.0 eq.) were placed in a round bottom flask and dissolved in PhMe (0.3 M). Pd(P( t -Bu) ₃ ) ₂ (9 mol%) was added dropwise under a bath temperature of 110 °C and stirred overnight. After the reaction, the organic layer was separated by washing with CH ₂ Cl ₂ /H ₂ O. Water was removed with MgSO ₄ and passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure and purified by column chromatography to prepare compound 1-e (9.5 g, 74% yield).

m/z [M+H] ⁺ C ₅₄ H ₅₈ N ₃ ⁺ 748.6

Step 1-3: Synthesis of intermediate compound 1-f

Compound 1-e (3.0 g, 1.0 eq.), compound 10-c (3.3 eq.), and NaO t -Bu (6.0 eq.) were placed in a round bottom flask and dissolved in PhMe (0.3 M). Pd(P( t -Bu) ₃ ) ₂ (9 mol%) was added dropwise under a bath temperature of 110 °C and stirred overnight. After the reaction, the organic layer was separated by washing with CH ₂ Cl ₂ /H ₂ O. Water was removed with MgSO ₄ and passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure and purified by column chromatography to prepare compound 1-f (5.0 g, 64% yield).

m/z [M+H] ⁺ C ₁₃₅ H ₁₄₈ Cl ₃ N ₆ ⁺ 1958.1

Steps 1-4: final body Synthesis of compound 1

Compound 1-f (1.0 eq.) was placed in a round bottom flask and dissolved in 1,2-dichlorobenzene (0.02 M). BI ₃ (2.0 eq.) was slowly added dropwise to the reaction mass stirred at room temperature, and the bath temperature was raised to 80 °C and stirred overnight. After the reaction, the reactant is sufficiently cooled at room temperature and diluted with CH ₂ Cl ₂ . To the reactant, sat.Na ₂ S ₂ O ₃ (aq.) and EtN i -Pr ₂ (15 eq.) were sequentially added dropwise to terminate the reaction, and washed with CH ₂ Cl ₂ /H ₂ O to separate the organic layer. Water was removed with MgSO ₄ and passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure and purified by column chromatography to prepare Compound 1.

m/z [M+H] ⁺ C ₁₃₅ H ₁₄₂ B ₃ N ₆ ⁺ 1880.2

production example 2: Preparation of compound 2

Step 2-1: Synthesis of intermediate compound 2-b

Compound 2-b was prepared in the same manner as in Compound 1-c, except that Compound 2-a was used instead of Compound 1-b.

m/z [M+H] ⁺ C ₂₄ H ₂₂ N ₃ ⁺ 352.2

Step 2-2: Synthesis of intermediate compound 2-c

Compound 2-c was prepared in the same manner as in Compound 1-e, except that Compound 2-b was used instead of Compound 1-c.

m/z [M+H] ⁺ C ₅₄ H ₅₈ N ₃ ⁺ 748.6

Step 2-3: Synthesis of intermediate compound 2-d

Compound 2-d was prepared in the same manner as in Compound 1-f, except that Compound 2-c was used instead of Compound 1-e.

m/z [M+H] ⁺ C ₁₃₅ H ₁₄₈ Cl ₃ N ₆ ⁺ 1958.1

Step 2-4: final body Synthesis of compound 2

Compound 2 was prepared in the same manner as in Compound 1, except that Compound 2-d was used instead of Compound 1-f.

m/z [M+H] ⁺ C ₁₃₅ H ₁₄₂ B ₃ N ₆ ⁺ 1880.2

production example 3: Preparation of compound 3

Step 3-1: Synthesis of intermediate compound 3-b

Compound 3-b was prepared in the same manner as in Compound 1-c, except that Compound 11-a was used instead of Compound 1-b.

m/z [M+H] ⁺ C ₂₄ H ₂₂ N ₃ ⁺ 352.2

Step 3-2: Synthesis of intermediate compound 3-b

Compound 3-c was prepared in the same manner as in Compound 1-e, except that Compound 3-b was used instead of Compound 1-c.

m/z [M+H] ⁺ C ₅₄ H ₅₈ N ₃ ⁺ 748.6

Step 3-3: Synthesis of intermediate compound 3-d

Compound 3-d was prepared in the same manner as in Compound 1-f, except that Compound 3-c was used instead of Compound 1-e.

m/z [M+H] ⁺ C ₁₃₅ H ₁₄₈ Cl ₃ N ₆ ⁺ 1958.1

Step 3-4: final body Synthesis of compound 3

Compound 3 was prepared in the same manner as in Compound 1, except that Compound 3-d was used instead of Compound 1-f.

m/z [M+H] ⁺ C ₁₃₅ H ₁₄₂ B ₃ N ₆ ⁺ 1880.2

production example 4: Preparation of compound 4

Step 4-1: Synthesis of intermediate compound 4-b

Compound 4-b was prepared in the same manner as in Compound 1-c, except that Compound 4-a was used instead of Compound 1-a.

m/z [M+H] ⁺ C ₂₁ H ₁₉ N ₆ ⁺ 355.2

Step 4-2: Synthesis of intermediate compound 4-c

Compound 4-c was prepared in the same manner as in Compound 1-e, except that Compound 4-b was used instead of Compound 1-c.

m/z [M+H] ⁺ C ₅₁ H ₅₅ N ₆ ⁺ 751.5

Step 4-3: Synthesis of intermediate compound 4-d

Compound 4-d was prepared in the same manner as in Compound 1-f, except that Compound 4-c was used instead of Compound 1-e.

m/z [M+H] ⁺ C ₁₃₂ H ₁₄₅ Cl ₃ N ₉ ⁺ 1961.1

Step 4-4: final body Synthesis of compound 4

Compound 4 was prepared in the same manner as in Compound 1, except that Compound 4-d was used instead of Compound 1-f.

m/z [M+H] ⁺ C ₁₃₂ H ₁₃₉ B ₃ N ₉ ⁺ 1883.2

production example 5: Preparation of compound 5

Step 5-1: Synthesis of compound 5-c

Compound 5-a (3.0 g, 1.0eq.), compound 5-b (1.03eq.) and K ₂ CO ₃ (2.0eq.) were placed in a round bottom flask and methylpyrrolidone (NMP) (0.3M) dissolve CuI (5 mol%) and iron (III)acetylacetonate (Fe(acac) ₃ ) (10 mol%) were added under a nitrogen atmosphere, and the temperature was raised to 150 °C and stirred for 4 hours. After the reaction, the reaction solution was cooled to room temperature and washed with EtOAc/sat.NH ₄ Cl (aq.) to separate the organic layer. Water was removed with MgSO ₄ and passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure and purified by column chromatography to obtain compound 5-c (5.1 g).

m/z [M+H] ⁺ C ₁₆ H ₁₉ O ₂ ⁺ 243.2

Step 5-2: Synthesis of intermediate compound 5-d

Compound 1-e (1.0 eq.), compound 5-c (3.3 eq.), and NaO t -Bu (6.0 eq.) were placed in a round bottom flask and dissolved in anhydrous toluene. Thereafter, nitrogen gas was charged for 10 minutes and stirred at room temperature, and the oil container temperature was raised from room temperature to 110 °C. Then, when the internal temperature reached 60 °C, Pd(( t -Bu) ₃ P) ₂ (9 mol%) was added dropwise, followed by stirring overnight. After the reaction, the organic layer was separated by washing with CH ₂ Cl ₂ /H ₂ O. Water was removed with MgSO ₄ and passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure and purified by column chromatography to obtain compound 5-d (5.2 g).

m/z [M+H] ⁺ C ₁₀₂ H ₁₀₆ N ₃ O ₃ ⁺ 1420.8

Step 5-3: Synthesis of final compound 5

Compound 5-d (1.0 eq.) was placed in a round bottom flask and dissolved in anhydrous 1,2-dichlorobenzene (0.02 M). BI ₃ (2.0 eq.) was slowly added dropwise to the stirred reaction product at room temperature, and the bath temperature was adjusted to 130°C and stirred overnight. After the reaction, the reactant is sufficiently cooled at room temperature and diluted with CH ₂ Cl ₂ . To the reactant, sat.Na ₂ S ₂ O ₃ (aq.) and EtN i -Pr ₂ (15 eq.) were sequentially added dropwise to terminate the reaction, and washed with CH ₂ Cl ₂ /H ₂ O to separate the organic layer. Water was removed with MgSO ₄ and passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure, and purified by column chromatography to prepare a final compound 5.

m/z [M+H] ⁺ C ₁₀₂ H ₉₇ B ₃ N ₃ O ₃ ⁺ 1444.8

[ Comparative Preparation Example ]

Comparative Preparation Example 1: Preparation of comparative compound E

Step E-1: Synthesis of intermediate compound E-b

Compound 1-a (3.0 g, 1.0 eq.), Compound Ea (1.03 eq.) and K ₂ CO ₃ (2.0 eq.) were placed in a round bottom flask and dissolved in NMP (0.3 M). CuI (5 mol%) and Fe(acac) ₃ (10 mol%) were added under a nitrogen atmosphere, the temperature was raised to 150 °C, and the mixture was stirred for 4 hours. After the reaction, the reaction solution was cooled to room temperature and washed with EtOAc/sat.NH ₄ Cl (aq.) to separate the organic layer. Water was removed with MgSO ₄ and passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure and purified by column chromatography to prepare compound Eb (28.0 g, 87% yield).

m/z [M+H] ⁺ C ₁₇ H ₁₉ Cl ₂ O ⁺ 309.1

Step E-2: Synthesis of intermediate compound E-d

Compound E-d was prepared in the same manner as in Compound 1-c, except that Compound E-c was used instead of Compound 1-b.

m/z [M+H] ⁺ C ₂₄ H ₁₉ O ₃ ⁺ 355.2

Step E-3: Synthesis of intermediate compound E-e

Compound Ed (3.0 g, 1.0 eq.), Compound Eb (3.6 eq.) and K ₂ CO ₃ (6.0 eq.) were placed in a round bottom flask and dissolved in NMP (0.3 M). CuI (15 mol%), Fe(acac) ₃ under nitrogen atmosphere (30 mol%) was added, the temperature was raised to 150 °C, and the mixture was stirred overnight. After the reaction, the reaction solution was cooled to room temperature and washed with EtOAc/sat.NH ₄ Cl (aq.) to separate the organic layer. Water was removed with MgSO ₄ and passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure and purified by column chromatography to prepare compound Ee (9.8 g, 59% yield).

m/z [M+H] ⁺ C ₇₅ H ₇₀ Cl ₃ O ₆ ⁺ 1171.4

Step E-4: final body Synthesis of compound E

Compound E was prepared in the same manner as in Compound 1, except that Compound E-e was used instead of Compound 1-f.

m/z [M+H] ⁺ C ₇₅ H ₆₄ B ₃ O ₆ ⁺ 1093.7

Example 1: Manufacture of organic light emitting device

A glass substrate coated with indium tin oxide (ITO) to a thickness of 500 Å was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, a product manufactured by Fischer Co. was used as the detergent, and distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic cleaning was performed with a solvent of isopropyl and acetone and dried. After washing the substrate for 5 minutes, the substrate was transported to a glove box.

On the ITO transparent electrode, spin coating (4000 rpm) a coating composition in which the compound O and compound P (weight ratio of 2:8) were dissolved in cyclohexanone at 20 wt/v%, and heat treatment (curing) at 200 °C for 30 minutes ) to form a hole injection layer to a thickness of 400 Å.

A coating composition in which the compound Q (Mn: 27,900; Mw: 35,600; GPC using PC Standard using Agilent 1200 series) was dissolved in toluene at 6 wt/v% on the hole injection layer was spin-coated ( 4000 rpm) and heat treatment at 200 °C for 30 minutes to form a hole transport layer having a thickness of 200 Å.

On the hole transport layer, a coating composition prepared by dissolving Compound 1 and Compound R (weight ratio of 2:98) at 2 wt/v% in cyclohexanone at 2 wt/v% was spin-coated (4000 rpm) and heat-treated at 180° C. for 30 minutes. A light emitting layer was formed to a thickness of 400 Å.

After transferring to a vacuum evaporator, the compound S was vacuum deposited to a thickness of 350 Å on the light emitting layer to form an electron injection and transport layer. A cathode was formed by sequentially depositing LiF to a thickness of 10 Å and aluminum to a thickness of 1000 Å on the electron injection and transport layer.

In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.7 Å/sec, the deposition rate of 0.3 Å/sec for LiF and 2 Å/sec for aluminum was maintained, and the vacuum degree during deposition was 2 Х 10 ^-7 to 5 Х 10 ^-8 torr was maintained.

Example 2 to 5

An organic light emitting diode was manufactured in the same manner as in Example 1, except that the compound shown in Table 1 (the following compound) was used instead of Compound 1 as a dopant for the emission layer.

comparative example 1 to 5

An organic light emitting diode was manufactured in the same manner as in Example 1, except that the compound shown in Table 1 (the compound below) was used instead of Compound 1 as a dopant for the emission layer.

Experimental example 1: Evaluation of characteristics of organic light emitting devices

When a current was applied to the organic light emitting diodes prepared in Examples and Comparative Examples, the driving voltage at a current density of 10 mA/cm ² , external quantum efficiency (EQE), and lifespan were measured. Table 1 shows. At this time, the external quantum efficiency (EQE) was calculated as “(the number of emitted photons) / (the number of injected charge carriers) * 100”, and T90 is the time it takes for the luminance to decrease from the initial luminance (500 nit) to 90%. means

compound
(Emissive layer dopant) drive voltage
(V
@10mA/cm ² ) EQE
(%
@10mA/cm ² ) Lifetime (hr)
(T90
@500 nits) Example 1 compound 1 4.61 9.03 123 Example 2 compound 2 4.60 9.02 121 Example 3 compound 3 4.59 9.12 125 Example 4 compound 4 4.60 9.02 122 Example 5 compound 5 4.58 8.99 120 Comparative Example 1 compound A 4.61 6.72 60 Comparative Example 2 compound B 4.60 6.89 58 Comparative Example 3 compound C 4.59 6.99 52 Comparative Example 4 compound D 4.58 6.23 49 Comparative Example 5 compound E 4.67 8.34 100

As shown in Table 1, it can be seen that the organic light emitting device using the compound of the present invention as a dopant for the light emitting layer exhibits very excellent characteristics in terms of lifespan compared to the organic light emitting device using the compound of Comparative Example as a dopant for the light emitting layer. .

Specifically, in Comparative Example 1 using a general dopant, it was confirmed that the lifespan of the organic light emitting diode was improved as compared to Examples 1 to 5 of the present application.

In addition, the compound of Comparative Example 2 is different in that a nitrogen atom is substituted at the boron atom position. The compound of Comparative Example 3 has a structure different from that of the boron heterocyclic ring of the present invention. In addition, Comparative Example 4 is different in that it is a monomer including only one boron heterocycle of the present invention. In addition, the compound of Comparative Example 5 is different in that Y is all CH, and X ₁ and X ₂ are both O. Therefore, it was confirmed that when the compound of Formula 1 of the present invention was applied to an organic light emitting device due to this difference, there was an effect of long life.

1: Substrate
2: Anode
3: light emitting layer
4: cathode
5: hole injection layer
6: hole transport layer
7: light emitting layer
8: electron injection and transport layer

Claims (16)

A compound represented by the following formula (1):
[Formula 1]

In Formula 1,
X ₁ and X ₂ are each independently N(R ₃ ), O, or S,
each Y is independently CH, or N;
R ₁ and R ₂ are each independently hydrogen; heavy hydrogen; Or a C _1-60 alkyl group substituted or unsubstituted with deuterium;
R ₃ is hydrogen; heavy hydrogen; Or an alkyl group, an alkoxy group, a silyl group, an amine group, an aryl group and a C _6-60 aryl group unsubstituted or substituted with one or two or more substituents selected from the group consisting of a heteroaryl group,
n1 is each independently an integer of 1 to 3,
n2 is each independently an integer of 1 to 4,
When Y is all CH, at least one of X ₁ and X ₂ is N(R ₃ ) or S. The method according to claim 1,
X ₁ is the same as each other and X ₂ is the same as each other. The method according to claim 1, wherein X ₁ and X ₂ are N(R ₃ ), wherein R ₃ is substituted or unsubstituted with a substituent selected from the group consisting of an alkyl group, an alkoxy group, a silyl group, an amine group, an aryl group, and a heteroaryl group. A compound that is a cyclic C _6-60 aryl group. The compound of claim 1, wherein Y is the same as each other. The compound of claim 1, wherein R ₁ and R ₂ are each independently hydrogen or a C _1-10 alkyl group. The compound of claim 1, wherein R ₁ and R ₂ are each independently hydrogen, a methyl group, or a tert-butyl group. The method according to claim 1, R ₃ are each independently hydrogen, or a phenyl group,
The phenyl group is unsubstituted or substituted with a C _1-10 alkyl group, a C _1-10 alkoxy group, a tri(C _1-10 alkyl)silyl group, a 9-phenyl-carbazolyl group, or a carbazol-9-yl group. . The method according to claim 1, R ₃ are each independently hydrogen, or a phenyl group,
The phenyl group is unsubstituted; or a compound substituted with a methyl group, a tert-butyl group, a methoxy group, a trimethylsilyl group, a tri(isopropyl)silyl group, a 9-phenyl-carbazolyl group, or a carbazol-9-yl group. The method according to claim 1, wherein the compound represented by Formula 1 is any one selected from the following structural formula:

10. A coating composition comprising a compound according to any one of claims 1 to 9. 11. The method of claim 10,
The coating composition is a coating composition for an organic light emitting device. a first electrode; a second electrode provided to face the first electrode; and
An organic light emitting device comprising one or more organic material layers provided between the first electrode and the second electrode,
At least one of the organic material layers is an organic light-emitting device comprising the coating composition according to claim 10 or a cured product thereof. The organic light emitting device of claim 12 , wherein the organic material layer includes a light emitting layer, and the light emitting layer includes the coating composition or a cured product thereof. The organic light emitting diode of claim 13, wherein the light emitting layer is a blue light emitting layer. 14. The method of claim 13, wherein the coating composition further comprises a host material,
An organic light emitting device comprising the compound and the host material in a weight ratio of 1:1 to 1:200. 14. The method of claim 13, wherein the coating composition further comprises a host material,
The host material is an organic light emitting device represented by the following formula (A):
[Formula A]

In Formula A, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
L20 is a direct bond; Or a substituted or unsubstituted arylene group,
R100 is hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
r100 is an integer of 0 to 8, and when r100 is 2 or more, R100 is the same as or different from each other.

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