KR102352350B1 - Copolymer and organic light emitting device comprising the same - Google Patents

Abstract

The present specification relates to a copolymer comprising a unit of Formula 1 to a unit of Formula 3; And it provides an organic light emitting device including the same.

Description

Copolymer, and an organic light emitting device comprising the same {COPOLYMER AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME}

The present specification relates to a copolymer, a coating composition comprising the copolymer, an organic light emitting device formed using the coating composition, and a method for manufacturing the same.

In general, the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon has a structure including an anode and a cathode and an organic material layer therebetween. Here, the organic material layer is often formed of a multi-layered 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, an electron injection layer, and the like. When a voltage is applied between the two electrodes in the structure of the organic light emitting device, 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.

Among soluble OLED (soluble OLED) materials, a curing machine is introduced to ensure solvent orthogonality in HTL materials. However, when the reaction temperature of the curing machine is high or the rigidity is high, there are problems such as not having solvent resistance or poor uniformity of the thin film, such as the resulting thin film after curing is dissolved in the upper layer solution .

The development of new materials for the organic light emitting device as described above is continuously required.

US Patent Application Publication No. 2004-0251816

The present specification provides a copolymer and an organic light emitting device including the same.

The present specification provides a copolymer including a unit of Formula 1 to a unit of Formula 3 below.

[Formula 1]

[Formula 2]

[Formula 3]

In Formulas 1 to 3,

Ar1 and Ar2 are the same as or different from each other, and are each independently a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

Ar3 is hydrogen; 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,

L1 is a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

R1 to R7 and R1' are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; thermosetting group; Or a photocurable group, combined with an adjacent substituent to form a substituted or unsubstituted hydrocarbon ring,

R6 and R7 may be connected to each other by a direct bond,

a is an integer of 0 to 4, and when a is plural, R1 are the same as or different from each other,

a' is an integer from 0 to 3, and when a' is plural, R1' is the same as or different from each other,

b is an integer from 0 to 6, and when b is plural, R4 is the same as or different from each other,

c is 0 or 4, and when c is plural, R5 is the same as or different from each other,

은 다른 치환기, 단량체 또는 결합부에 결합되는 부위를 의미한다.

denotes a site bound to another substituent, monomer, or binding moiety.

Another exemplary embodiment of the present specification provides a coating composition comprising the copolymer or a cured product thereof.

In addition, the first electrode; a second electrode provided to face the first electrode; and

One or more organic material layers are included between the first electrode and the second electrode,

At least one layer of the organic material layer provides an organic light emitting device comprising the coating composition or a cured product thereof.

Another exemplary embodiment of the present specification provides a method of manufacturing an organic light emitting device, wherein the step of forming an organic material layer formed using the coating composition or a cured product thereof includes a drying step after applying the coating composition.

The forward transport layer material using the copolymer of the present invention has high solubility in organic solvents and excellent hole transport properties in the device after film formation. In addition, it is not deformed by the additional solution process after the solution coating and heat treatment process, and the efficiency and lifespan can be improved.

1 illustrates an organic light emitting device according to an exemplary embodiment of the present specification.
2 is a mass spectral spectrum of monomer 1;

Hereinafter, the present specification will be described in detail.

An exemplary embodiment of the present specification provides a copolymer including the unit of Formula 1 to the unit of Formula 3 above.

An exemplary embodiment of the present specification provides a coating composition comprising the copolymer or a cured product thereof.

An exemplary embodiment of the present specification includes a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer between the first electrode and the second electrode, wherein at least one of the organic material layers provides an organic light emitting device including the coating composition or a cured product thereof.

An exemplary embodiment of the present specification provides a method for manufacturing an organic light emitting device, wherein the forming using the coating composition includes a drying step after applying the coating composition.

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

In this 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 exists between the two members.

In the present specification, “combination” means connecting a plurality of structures or connecting different types of structures.

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

는 다른 치환기, 단량체 또는 결합부에 결합되는 부위를 의미한다.In this specification,

denotes a site bound to another substituent, a monomer, or a bonding moiety.

In the present specification, the monomer may mean a repeating unit included in the polymer.

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

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

As used herein, the term "substituted or unsubstituted" refers to deuterium; halogen group; nitrile group; nitro group; imid; amide group; carbonyl group; ester group; hydroxyl group; an alkyl group; cycloalkyl group; alkoxy group; aryloxy group; alkyl thiooxy group; arylthioxy group; an alkyl sulfoxy group; arylsulfoxy group; alkenyl group; silyl group; siloxane group; boron group; amine group; an arylphosphine group; a phosphine oxide group; aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, is substituted with a substituent to which two or more of the above-exemplified substituents are connected, or does not have any substituents. 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, and may be interpreted as a substituent in which two phenyl groups are connected.

In the present specification, the halogen group may be fluorine, chlorine, bromine or iodine.

In the present specification, the number of carbon atoms in the carbonyl group is not particularly limited, but preferably 1 to 30 carbon atoms.

In the present specification, in the ester group, oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 30 carbon atoms.

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-dimethyl heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl, and the like.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, and 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, etc., but are limited thereto it is not

In the present specification, the amine group is -NH ₂ ; an alkylamine group; N-arylalkylamine group; arylamine group; N-aryl heteroarylamine group; It may be selected from the group consisting of an N-alkylheteroarylamine group and a heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, and a 9-methyl-anthracenylamine group. , diphenylamine group, N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, and the like, but is not limited thereto.

In the present specification, the N-alkylarylamine group refers to an amine group in which an alkyl group and an aryl group are substituted with N of the amine group.

In the present specification, the N-arylheteroarylamine group refers to an amine group in which an aryl group and a heteroaryl group are substituted with N of the amine group.

In the present specification, the N-alkylheteroarylamine group refers to an amine group in which an alkyl group and a heteroarylamine group are substituted with N of the amine group.

In the present specification, the alkyl group in the alkylamine group, N-arylalkylamine group, alkylthioxy group, alkylsulfoxy group, and N-alkylheteroarylamine group is the same as the above-described alkyl group. Specifically, the alkyl thiooxy group includes a methyl thioxy group, ethyl thiooxy group, tert-butyl thioxy group, hexyl thioxy group, octyl thiooxy group, etc., and the alkyl sulfoxy group includes mesyl, ethyl sulfoxy group, propyl sulfoxy group, butyl sulfoxy group and the like, but is not limited thereto.

In the present specification, the aryl group may be monocyclic or polycyclic.

When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but preferably 6 to 30 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, and the like, but is not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. It is preferable that it is C10-30. Specifically, the polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, and the like, but is not limited thereto.

In the present specification, the fluorenyl group may be substituted, and adjacent substituents may combine with each other to form a ring.

,

,

및

등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

,

and

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

In the present specification, the aryl group in the aryloxy group, the arylthioxy group, the arylsulfoxy group, the N-arylalkylamine group, the N-arylheteroarylamine group and the arylphosphine group is the same as the above-described aryl group. Specifically, the aryloxy group includes a phenoxy group, p-tolyloxy group, m-tolyloxy group, 3,5-dimethyl-phenoxy group, 2,4,6-trimethylphenoxy group, p-tert-butylphenoxy group, 3- Biphenyloxy group, 4-biphenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthryloxy group , 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group, 9-phenanthryloxy group, and the like, and the arylthioxy group includes phenylthioxy group, 2- There are a methylphenylthioxy group, a 4-tert-butylphenylthioxy group, and the like, and the arylsulfoxy group includes a benzenesulfoxy group and a p-toluenesulfoxy group, but is not limited thereto.

In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group including two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time. For example, the aryl group in the arylamine group may be selected from the examples of the aryl group described above.

In the present specification, the heterocyclic group includes at least one atom or a heteroatom other than carbon, and specifically, the heteroatom may include at least one atom selected from the group consisting of O, N, Se and S, and the like. The number of carbon atoms is not particularly limited, but preferably has 2 to 30 carbon atoms, and the heterocyclic group may be monocyclic or polycyclic. Examples of the heterocyclic group include a thiophene group, a furanyl group, a pyrrole group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazinyl group, a triazinyl group Jolyl group, acridyl group, pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group , isoquinolinyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, benzothiophene group, dibenzothiophene group, benzofuranyl group, pe Nonthrolinyl group (phenanthroline), thiazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, phenothiazinyl group, dibenzofuranyl group, and the like, but are not limited thereto.

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

In the present specification, examples of the heteroaryl group in the N-arylheteroarylamine group and the N-alkylheteroarylamine group are the same as the examples of the heterocyclic group described above.

In an exemplary embodiment of the present specification, Formula 1 may be Formula 4 below.

[Formula 4]

In Formula 4, Ar1 to Ar3, L1, R1, R1', a and a' are as defined in Formulas 1 to 3.

In the exemplary embodiment of the present specification, Chemical Formula 3 may be selected from the following Chemical Formulas 5 to 7.

[Formula 5]

[Formula 6]

[Formula 7]

In Formulas 5 to 7, R5 and R5' are the same as defined for R5 in Formula 3 above.

According to an exemplary embodiment of the present specification, the copolymer includes one or two or more units represented by any one of the following Chemical Formulas 1-1 to 1-3.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Formulas 1-1 to 1-3,

Ar1 and Ar2 are the same as or different from each other, and are each independently a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

Ar3 is hydrogen; 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,

L1 is a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

R1 to R7, and R1' to R4' are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; thermosetting group; Or a photocurable group, combined with an adjacent substituent to form a substituted or unsubstituted hydrocarbon ring,

R6 and R7 may be connected to each other by a direct bond,

a is an integer of 0 to 4, and when a is plural, R1 are the same as or different from each other,

a' is an integer from 0 to 3, and when a' is plural, R1' is the same as or different from each other,

b and b' are integers from 0 to 6, and when b and b' are plural, R4 and R4' are the same as or different from each other;

c is 0 to 4, and when c is plural, R5 is the same as or different from each other,

은 다른 치환기, 단량체 또는 결합부에 결합되는 부위를 의미한다.

denotes a site bound to another substituent, monomer, or binding moiety.

According to an exemplary embodiment of the present specification, the copolymer includes one or two or more units represented by the following Chemical Formulas 1-4 to 1-6.

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

In Formulas 1-4 to 1-6, Ar1 to Ar3, L1, R1 to R7, R1' to R4', a to c, a' and b' are defined in Formulas 1-1 to 1 of claim 3 As defined in -3,

o, p, and q are the molar ratios of each display unit, based on o+p=1 or o+q=1,

o is a molar ratio of 0.05 to 0.95,

p is a molar ratio of 0.05 to 0.95,

q is a molar ratio of 0.05 to 0.95,

Based on o+p+q=1,

o is a molar ratio of 0.025 to 0.95,

p is a molar ratio of 0.025 to 0.95,

q is a molar ratio of 0.025 to 0.95.

In an exemplary embodiment of the present specification, R1 to R7, and R1' to R5' are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; thermosetting group; Or it is a photocurable group, or combines with an adjacent substituent to form a substituted or unsubstituted hydrocarbon ring.

In an exemplary embodiment of the present specification, R1 and R4 are hydrogen.

In an exemplary embodiment of the present specification, R1' and R4' are hydrogen.

In an exemplary embodiment of the present specification, R2 and R3 are the same as or different from each other, and each independently represent an alkyl group having 1 to 10 carbon atoms.

In an exemplary embodiment of the present specification, R2' and R3' are the same as the definitions of R2 and R3.

In an exemplary embodiment of the present specification, R5 and R5' are hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or is selected from the following structural formula.

In the above structural formula,

Ri to Riv are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

Rv is O, a substituted or unsubstituted alkylene group, a substituted or unsubstituted alkoxyylene group, or a substituted or unsubstituted arylene group,

r is an integer from 0 to 4,

When r is plural, Riv is the same as or different from each other,

s is an integer from 0 to 5,

When s is plural, Riii is the same as or different from each other.

In an exemplary embodiment of the present specification, R5 and R5' are an alkoxy group unsubstituted or substituted with an aryl group substituted with an alkenyl group.

In an exemplary embodiment of the present specification, R5 and R5' are an alkoxy group having 1 to 20 carbon atoms.

In an exemplary embodiment of the present specification, R5 and R5' are methoxy groups unsubstituted or substituted with a styrene group.

In an exemplary embodiment of the present specification, R5 and R5' combine with an adjacent substituent to form a substituted or unsubstituted hydrocarbon ring.

In an exemplary embodiment of the present specification, R5 and R5' combine with an adjacent substituent to form a substituted benzene ring.

In an exemplary embodiment of the present specification, R6 and R7 are connected to each other by a direct bond.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.

In an exemplary embodiment of the present specification, Ar1 and A2 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted monocyclic arylene group; a substituted or unsubstituted polycyclic arylene group; Or a substituted or unsubstituted heteroarylene group.

In an exemplary embodiment of the present specification, Ar1 and A2 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted monocyclic arylene group; or a substituted or unsubstituted polycyclic arylene group.

In an exemplary embodiment of the present specification, Ar1 and A2 are phenylene groups.

In an exemplary embodiment of the present specification, Ar3 is hydrogen; 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.`

In an exemplary embodiment of the present specification, Ar3 is hydrogen; 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.

In an exemplary embodiment of the present specification, Ar3 is an aryl group unsubstituted or substituted with an alkyl group.

In an exemplary embodiment of the present specification, Ar3 is a phenyl group, a biphenyl group, or a dimethylfluorene group.

In an exemplary embodiment of the present specification, Ar3 is a heteroaryl group containing substituted or unsubstituted N, O, or S.

In an exemplary embodiment of the present specification, L1 is a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.

In an exemplary embodiment of the present specification, L1 is a direct bond; or a phenylene group.

According to an exemplary embodiment of the present specification, the copolymer has a number average molecular weight of 100 to 100,000,000 g/mol.

According to an exemplary embodiment of the present specification, the copolymer has a number average molecular weight of 1,000 to 10,000,000 g/mol.

According to an exemplary embodiment of the present specification, the copolymer is a copolymer having any one of the following structures.

In the structural formula, o, p, and q are molar ratios of each display unit, and when o+p=1 or o+q=1,

o is a molar ratio of 0.05 to 0.95,

p is a molar ratio of 0.05 to 0.95,

q is a molar ratio of 0.05 to 0.95,

Based on o+p+q=1,

o is a molar ratio of 0.025 to 0.95,

p is a molar ratio of 0.025 to 0.95,

q is a molar ratio of 0.025 to 0.95.

According to an exemplary embodiment of the present specification, o is a molar ratio of 0.5 to 0.9.

According to an exemplary embodiment of the present specification, p is a molar ratio of 0.1 to 0.5.

According to an exemplary embodiment of the present specification, q is a molar ratio of 0.1 to 0.5.

According to an exemplary embodiment of the present specification, the end of the copolymer may be hydrogen, or a substituted or unsubstituted aryl group.

According to an exemplary embodiment of the present specification, the end of the copolymer may be an aryl group unsubstituted or substituted with hydrogen or an alkyl group.

According to an exemplary embodiment of the present specification, the terminal of the copolymer may be an aryl group unsubstituted or substituted with hydrogen or a linear or branched alkyl group having 1 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, the terminal of the copolymer may be an aryl group having 6 to 20 carbon atoms that is unsubstituted or substituted with hydrogen or a straight or branched chain alkyl group having 1 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, the end of the copolymer may be hydrogen, a phenyl group, or a 4-tertbutylphenyl group.

According to an exemplary embodiment of the present specification, the coating composition includes the copolymer.

According to an exemplary embodiment of the present specification, the coating composition includes the copolymer in the range of 0.1 to 30 wt%.

According to an exemplary embodiment of the present specification, the coating composition includes the copolymer in the range of 0.1 to 10 wt%.

When the content of the copolymer in the coating composition is less than the above range, the process time for coating to a desired thickness increases, and when it is high, the viscosity increases and coating is difficult.

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 copolymer.

For example, the structure of the organic light emitting device of the present invention may have a structure as shown in FIG. 1 , but is not limited thereto.

1 illustrates a structure of an organic light emitting device in which a first electrode 2 , an organic material layer 3 , a light emitting layer 4 , and a second electrode 5 are sequentially stacked on a substrate 1 .

In one embodiment of the present invention, the organic material layer comprising the coating composition or a cured product thereof includes at least one of an electron injection layer, an electron transport layer, and a layer that simultaneously injects and transports electrons, and at least one of the layers The layer may include the coating composition and a cured product thereof.

In an exemplary embodiment of the present invention, the coating composition or a cured product thereof may be included in a hole injection layer, a hole transport layer, or a layer that simultaneously injects and transports holes.

In an exemplary embodiment of the present invention, the coating composition or a cured product thereof may be included in an electron injection layer, an electron transport layer, or a layer that simultaneously injects and transports electrons.

For example, the organic light emitting device according to the present invention uses a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, to form a metal or a conductive metal oxide or an alloy thereof on a substrate. is deposited to form an anode, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an organic material layer including the copolymer can be In addition to this method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

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 that can be used in the present invention 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); ZnO:Al or SnO ₂ : a combination of a metal such as Sb and an oxide; poly(3-methyl compound), poly[3,4-(ethylene-1,2-dioxy) compound] (PEDT), polypyrrole, and conductive polymers such as 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 negative electrode 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 material is a material capable of well injecting holes from the anode at a low voltage, and it is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based organic material. of organic substances, anthraquinones, and conductive polymers based on polyaniline and polycompounds, but is not limited thereto.

As the hole transport material, a material capable of transporting holes from an anode or a hole injection layer to the light emitting layer is suitable, and a material having high hole mobility is suitable. Specific examples include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together.

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, etc., and heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

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

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 copolymer.

For example, the organic light emitting device of the present specification 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 forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to this method, an organic light emitting diode may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

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

Specifically, in one embodiment of the present specification, preparing a substrate; forming a cathode or an anode on the substrate; forming one or more organic material layers on the cathode or anode; and forming an anode or a cathode on the organic material layer, wherein at least one of the organic material layers is formed using the coating composition or a cured product thereof.

The step of forming one or more layers of the organic material layer using the coating composition may include a drying step after applying the coating composition. If necessary, the drying step may include a curing step.

In one embodiment of the present specification, the organic material layer formed using the coating composition is formed using a solution process.

In another embodiment, the organic material layer formed using the coating composition is formed by a printing method.

In the present specification, the printing method includes, for example, inkjet printing, nozzle printing, offset printing, transfer printing, or screen printing, but is not limited thereto.

Since the coating composition according to an exemplary embodiment of the present specification is suitable for a solution process due to structural characteristics, it can be formed by a printing method, so that it is economically effective in terms of time and cost when manufacturing a device.

In one embodiment of the present specification, the step of forming the organic material layer formed using the coating composition includes heat treatment or vacuum drying. Residual solvent is removed through the heat treatment or vacuum drying step.

In an exemplary embodiment of the present specification, the heat treatment or vacuum drying may include a curing step.

In one embodiment of the present specification, as the polymer binder, one that does not extremely inhibit charge transport and does not have strong absorption for visible light is preferably used. Examples of the polymer binder include poly(N-vinylcarbazole), polyaniline and its derivatives, polythiophene and its derivatives, poly(p-phenylenevinylene) and its derivatives, poly(2,5-thienylenevinylene) and Derivatives thereof, polycarbonate, polyacrylate, polymethyl acrylate, polymethyl methacrylate, polystyrene, polyvinyl chloride, polysiloxane and the like are exemplified.

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 material is a layer that receives electrons from the electron injection layer and transports them to the light emitting layer. This is suitable. Specific examples include Al complex of 8-hydroxyquinoline; complexes comprising Alq3; 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 It is preferable to use a compound which prevents movement to a layer and is excellent in the ability to form a thin film. 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 specification may be a top emission type, a back emission type, or a double side emission type depending on the material used.

The method for preparing the copolymer and the preparation of an organic light emitting device using them 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.

Preparation Example 1. Preparation of Monomer 1

(4-([1,1'-biphenyl]-4-yl(9,9-dimethyl-9H-fluoren-3-yl)amino)phenyl)boronic acid (5g, 10.39mmol), tris(4- Add bromophenyl)amine (14.92g, 31.1mmol), 2M K ₂ CO ₃ 30mL, tetrakistriphenylphosphine palladium(0) (0.6g), 100mL toluene and heat to 90°C. The temperature was raised and stirred for 48 hours. The temperature was lowered, precipitated in methanol, filtered, dissolved in dichloromethane, and washed with water. After removing the solvent, it was dissolved in tetrahydrofuran (THF), precipitated in methanol, filtered, dried, and purified by silica gel column chromatography.

2 is a mass spectral spectrum result of the monomer 1;

production example 2. Preparation of copolymer 1

2,2'-(9,9-dioctyl-9H-fluorene-2,7-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (0.8452 g, 1.31 mmol), N-([1,1'-biphenyl]-4-yl)-N,N-bis(4-bromophenyl)-N4-(9,9-dimethyl-9H-fluoren- 2-yl)-[1,1'-biphenyl]-4,4'-diamine (0.660 g, 0.789 mmol), 4,4'-(((2,5-dibromo-1,4-phenyl) Ren)bis(oxy))bis(methylene))bis(vinylbenzene) (0.262g, 0.526mmol) was added to 100mL RBF and dissolved in 15mL toluene, followed by 20wt% aq. Et ₄ NOH (5mL) was added, the temperature was raised to 90 °C, and the mixture was stirred for 30 minutes. Tetrakistriphenylphosphine palladium (0) (Tetrakistriphenylphosphine palladium (0)) (76 mg) was dissolved in 5 mL toluene, put at a time, and stirred for 48 hours. After lowering the temperature, it was precipitated in methanol, filtered, washed with methanol, water, ethanol, and hexane, dissolved in methylene chloride, charcoal, CPS-T, and MgSO ₄ were added, and stirred at room temperature for 30 minutes. The stirred mixture was passed through triethylamine-treated silica, methylene chloride was removed, dissolved in a small amount of toluene, adsorbed to triethylamine-treated silica, and then loaded onto a column and washed with hexane. Then, it was dissolved again in the column with toluene to remove the toluene, and only a portion was left behind, precipitated in methanol, filtered, and dried.

The number average molecular weight is 61,000 g/mol, and the weight evaluation molecular weight is 111,200 g/mol.

production example 3. Preparation of copolymer 2

2,2'-(9,9-dioctyl-9H-fluorene-2,7-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (2 g , 3.11 mmol), 4-bromo-N- (4-bromophenyl) -N- (4- (9-phenyl-9H-carbazol-3-yl) phenyl) aniline (1.199 g, 1.87 mmol), 2,6-dibromo-3,7-bis((2-octyldodecyl)oxy)naphthalene (0.546 g, 0.622 mmol), 4,4'-(((2,5-dibromo-1, 4-phenylene)bis(oxy))bis(methylene))bis(vinylbenzene) (0.310g, 0.622mmol) was added to 100mL RBF and dissolved in 30mL toluene, followed by 20wt% aq. Et ₄ NOH (10 mL) was added, the temperature was raised to 90 °C, and the mixture was stirred for 30 minutes. Tetrakistriphenylphosphine palladium (0) (Tetrakistriphenylphosphine palladium (0)) (89 mg) was dissolved in 5 mL toluene, put at a time, and stirred for 48 hours. After lowering the temperature, it was precipitated in methanol, filtered, washed with methanol, water, ethanol, and hexane, dissolved in methylene chloride, charcoal, CPS-T, and MgSO ₄ were added, and stirred at room temperature for 30 minutes. The stirred mixture was passed through triethylamine-treated silica, methylene chloride was removed, dissolved in a small amount of toluene, adsorbed to triethylamine-treated silica, and then loaded onto a column and washed with hexane. Then, it was dissolved again in the column with toluene to remove the toluene, and only a portion was left behind, precipitated in methanol, filtered, and dried.

The number average molecular weight is 21,000 g/mol, and the weight evaluation molecular weight is 45,000 g/mol.

production example 4. Preparation of copolymer 3

2,2'-(9,9-dioctyl-9H-fluorene-2,7-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (2 g , 3.11 mmol), 4-bromo-N- (4-bromophenyl) -N- (4- (9-phenyl-9H-carbazol-3-yl) phenyl) aniline (1.199 g, 1.87 mmol), 4,4'-(((2,5-dibromo-1,4-phenylene)bis(oxy))bis(methylene))bis(vinylbenzene) (0.622g, 1.245mmol) was put into 100mL RBF After dissolving in 30mL toluene, 20wt% aq. Et ₄ NOH (10 mL) was added, the temperature was raised to 90 °C, and the mixture was stirred for 30 minutes. Tetrakistriphenylphosphine palladium (0) (Tetrakistriphenylphosphine palladium (0)) (89 mg) was dissolved in 5 mL toluene, put at a time, and stirred for 48 hours. After lowering the temperature, it was precipitated in methanol, filtered, washed with methanol, water, ethanol, and hexane, dissolved in methylene chloride, charcoal, CPS-T, and MgSO ₄ were added, and stirred at room temperature for 30 minutes. The stirred mixture was passed through triethylamine-treated silica, methylene chloride was removed, dissolved in a small amount of toluene, adsorbed to triethylamine-treated silica, and then loaded onto a column and washed with hexane. Then, it was dissolved again in the column with toluene to remove the toluene, and only a portion was left behind, precipitated in methanol, filtered, and dried.

The number average molecular weight is 31,000 g/mol, and the weight evaluation molecular weight is 66,000 g/mol.

production example 5. Preparation of copolymer 4

2,2'-(9,9-dioctyl-9H-fluorene-2,7-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (2 g , 3.11 mmol), 4-bromo-N- (4-bromophenyl) -N- (4- (9-phenyl-9H-carbazol-3-yl) phenyl) aniline (1.605 g, 2.49 mmol), 2,7-dibromo-9,9-bis(4-vinylbenzyl)-9H-fluorene (0.3463g, 0.622mmol) was added to 100mL RBF and dissolved in 30mL toluene, followed by 20wt% aq. Et ₄ NOH (10 mL) was added, the temperature was raised to 90 °C, and the mixture was stirred for 30 minutes. Tetrakistriphenylphosphine palladium (0) (Tetrakistriphenylphosphine palladium (0)) (89 mg) was dissolved in 5 mL toluene, put at a time, and stirred for 48 hours. After lowering the temperature, it was precipitated in methanol, filtered, washed with methanol, water, ethanol, and hexane, dissolved in methylene chloride, charcoal, CPS-T, and MgSO ₄ were added, and stirred at room temperature for 30 minutes. The stirred mixture was passed through triethylamine-treated silica, methylene chloride was removed, dissolved in a small amount of toluene, adsorbed to triethylamine-treated silica, and then loaded onto a column and washed with hexane. Then, it was dissolved again in the column with toluene to remove the toluene, and only a portion was left behind, precipitated in methanol, filtered, and dried.

The number average molecular weight is 33,000 g/mol, and the weight evaluation molecular weight is 62,700 g/mol.

Preparation Example 6. Preparation of Comparative Copolymer 1

2,2'-(9,9-dioctyl-9H-fluorene-2,7-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (2 g , 3.11 mmol), 4-bromo-N- (4-bromophenyl) -N- (4- (9-phenyl-9H-carbazol-3-yl) phenyl) aniline (2.006 g, 3.11 mmol) Put in 100mL RBF, dissolve in 30mL toluene, and then 20wt% aq. Et ₄ NOH (10 mL) was added, the temperature was raised to 90 °C, and the mixture was stirred for 30 minutes. Tetrakistriphenylphosphine palladium (0) (Tetrakistriphenylphosphine palladium (0)) (89 mg) was dissolved in 5 mL toluene, put at a time, and stirred for 48 hours. After lowering the temperature, it was precipitated in methanol, filtered, washed with methanol, water, ethanol, and hexane, dissolved in methylene chloride, charcoal, CPS-T, and MgSO ₄ were added, and stirred at room temperature for 30 minutes. The stirred mixture was passed through triethylamine-treated silica, methylene chloride was removed, dissolved in a small amount of toluene, adsorbed to triethylamine-treated silica, and then loaded onto a column and washed with hexane. Then, it was dissolved again in the column with toluene to remove the toluene, and only a portion was left behind, precipitated in methanol, filtered, and dried.

The number average molecular weight is 73,000 g/mol, and the weight evaluation molecular weight is 160,000 g/mol.

Preparation Example 7. Preparation of Comparative Copolymer 2

2,2'-(9,9-dioctyl-9H-fluorene-2,7-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (2 g , 3.11 mmol), 4-bromo-N- (4-bromophenyl) -N- (4-butylphenyl) aniline (0.8576 g, 1.87 mmol), 4,4'-(((2,5-di Bromo-1,4-phenylene)bis(oxy))bis(methylene))bis(vinylbenzene) (0.622g, 1.245mmol) was added to 100mL RBF and dissolved in 30mL toluene, followed by 20wt% aq. Et ₄ NOH (10 mL) was added, the temperature was raised to 90 °C, and the mixture was stirred for 30 minutes. Tetrakistriphenylphosphine palladium (0) (Tetrakistriphenylphosphine palladium (0)) (89 mg) was dissolved in 5 mL toluene, put at a time, and stirred for 48 hours. After lowering the temperature, it was precipitated in methanol, filtered, washed with methanol, water, ethanol, and hexane, dissolved in methylene chloride, charcoal, CPS-T, and MgSO ₄ were added, and stirred at room temperature for 30 minutes. The stirred mixture was passed through triethylamine-treated silica, methylene chloride was removed, dissolved in a small amount of toluene, and adsorbed to triethylamine-treated silica, and then loaded onto a column and washed with hexane. Then, it was dissolved again in the column with toluene to remove the toluene, and only a portion was left behind, precipitated in methanol, filtered, and dried.

The number average molecular weight is 48,000 g/mol, and the weight evaluation molecular weight is 102,000 g/mol.

Example 1

A glass substrate on which indium tin oxide (ITO) was deposited to a thickness of 1500 Å was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. 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 washing with a solvent of isopropyl alcohol and acetone was performed for 30 minutes each and dried, and then the substrate was transported to a glove box.

On the prepared ITO transparent electrode, the following compound A and compound B were mixed at a weight ratio of 7:3, and a solution dissolved in 2 wt% in cyclohexanone was spin-coated to form a film to a thickness of 400 Å. This was heated at 220° C. for 30 minutes in a nitrogen atmosphere to form a hole injection layer. Then, Copolymer 1 was dissolved in toluene at 0.7 wt%, and spin-coated on the hole injection layer to form a film at 200 Å, and heated at 200° C. for 30 minutes under a nitrogen atmosphere to form a hole transport layer. After transferring to a vacuum evaporator, the following compounds 2 and 3 were vacuum-deposited to a thickness of 300 Å at a concentration of 8 wt% on the hole transport layer to form a light emitting layer. On the light emitting layer, the following compound 4 was vacuum deposited to a thickness of 200 Å to form an electron injection and transport layer. A cathode was formed by sequentially depositing LiF to a thickness of 12 Å and aluminum to a thickness of 2000 Å on the electron injection and transport layer.

[Compound A]

[Compound B]

In the above process, the deposition rate of organic material was maintained at 0.4~0.7Å/sec, the deposition rate of LiF of the cathode was maintained at 0.3Å/sec, and the deposition rate of aluminum was maintained at 2Å/sec, and the vacuum degree during deposition was 2x10 ^-7 ~ 5x10 ^{- 8} torr was maintained.

Then, sealing was performed by bonding sealing glass and a glass substrate to glass using a photocurable epoxy resin, and the organic electroluminescent element of a multilayer structure was produced. Subsequent operations were performed in the air and at room temperature (25°C).

Example 2

An organic light emitting diode was manufactured in the same manner as in Example 1, except that in Example 1, copolymer 2 was used instead of copolymer 1 for the hole transport layer.

Example 3

An organic light emitting diode was manufactured in the same manner as in Example 1, except that in Example 1, copolymer 3 was used instead of copolymer 1 for the hole transport layer.

Example 4

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Copolymer 4 was used instead of Copolymer 1 for the hole transport layer in Example 1.

Comparative Example 1

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Comparative Copolymer 1 was used instead of Copolymer 1 for the hole transport layer in Example 1.

Comparative Example 2

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Comparative Copolymer 2 was used instead of Copolymer 1 for the hole transport layer in Example 1.

Table 1 shows the results of measuring the driving voltage and efficiency of the organic light emitting diode manufactured by the above method at ^{a current density of 10 mA/cm 2 .}

Example hole transport layer Driving voltage (V) current efficiency
(cd/A) EQE (%) life time
(95%,h) Example 1 Copolymer 1 4.12 7.49 8.15 35 Example 2 copolymer 2 3.94 6.66 7.22 35 Example 3 copolymer 3 4.05 7.20 7.76 33 Example 4 Copolymer 4 4.20 7.59 8.31 31 Comparative Example 1 Comparative Copolymer 1 3.99 0.61 0.48 17 Comparative Example 2 Comparative copolymer 2 4.19 1.53 1.43 14

As shown in Table 1, copolymers 1 to 4 including Formulas 1 to 3 exhibit excellent efficiency and lifetime, but Comparative Example 1 not including the unit of Formula 3 and Comparative Example 2 not including the unit of Formula 1 were low. It can be seen that the efficiency and lifespan are indicated.

1: Substrate
2: first electrode
3: organic layer
4: light emitting layer
5: second electrode

Claims (12)

A copolymer comprising the following formulas 1-1 and 1-2, or comprising units of formulas 1-1 and 1-3:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Formulas 1-1 to 1-3,
Ar1 and Ar2 are the same as or different from each other, and are each independently a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Ar3 is hydrogen; 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,
L1 is a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
R1 to R7 and R1' to R4' are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; thermosetting group; Or a photocurable group, combined with an adjacent substituent to form a substituted or unsubstituted hydrocarbon ring,
R6 and R7 may be connected to each other by a direct bond,
a is an integer from 0 to 4, and when a is plural, R1 are the same as or different from each other,
a' is an integer from 0 to 3, and when a' is plural, R1' is the same as or different from each other,
b is an integer from 0 to 6, and when b is plural, R4 is the same as or different from each other,
c is 0 to 4, and when c is plural, R5 is the same as or different from each other,

denotes a site bound to another substituent, monomer, or binding moiety. The method according to claim 1, wherein R5 is hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or a copolymer selected from the following structural formula:

In the structural formula,
Ri to Riv are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
Rv is O, a substituted or unsubstituted alkylene group, a substituted or unsubstituted alkoxyylene group, or a substituted or unsubstituted arylene group,
r is an integer from 0 to 4,
When r is plural, Riv is the same as or different from each other,
s is an integer from 0 to 5,
When s is plural, Riii is the same as or different from each other. delete The method according to claim 1, wherein the copolymer is a copolymer comprising one or two or more units represented by the following Chemical Formulas 1-4 to 1-6:
[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

In Formulas 1-4 to 1-6,
The definitions of Ar1 to Ar3, L1, R1 to R7, R1' to R4', a to c, a' and b' are the same as those defined in Formulas 1-1 to 1-3 of claim 1,
o, p, and q are the molar ratios of each display unit, based on o+p=1 or o+q=1,
o is a molar ratio of 0.05 to 0.95,
p is a molar ratio of 0.05 to 0.95,
q is a molar ratio of 0.05 to 0.95,
Based on o+p+q=1,
o is a molar ratio of 0.025 to 0.95,
p is a molar ratio of 0.025 to 0.95,
q is a molar ratio of 0.025 to 0.95. The copolymer of claim 1, wherein the copolymer has any one of the following structures:

Wherein o, p, and q are molar ratios of each display unit, and when o+p=1 or o+q=1,
o is a molar ratio of 0.05 to 0.95,
p is a molar ratio of 0.05 to 0.95,
q is a molar ratio of 0.05 to 0.95,
Based on o+p+q=1,
o is a molar ratio of 0.025 to 0.95,
p is a molar ratio of 0.025 to 0.95,
q is a molar ratio of 0.025 to 0.95. The copolymer according to claim 1, wherein the copolymer has a number average molecular weight of 1,000 to 10,000,000 g/mol. A coating composition comprising the copolymer according to any one of claims 1, 2 and 4 to 6 above. a first electrode;
a second electrode provided to face the first electrode; and
One or more organic material layers are included between the first electrode and the second electrode,
At least one layer of the organic material layer is an organic light emitting device comprising the coating composition of claim 7 or a cured product thereof. 9. The method of claim 8,
The organic layer includes a hole transport layer, a hole injection layer, or a layer that simultaneously transports and injects holes,
The hole transport layer, the hole injection layer, or the layer for both hole transport and hole injection at the same time is an organic light emitting device comprising the coating composition or a cured product thereof. 9. The method of claim 8,
The organic layer includes an electron injection layer, an electron transport layer, or a layer that simultaneously injects and transports electrons,
The electron injection layer, the electron transport layer, or the layer for injecting and transporting electrons at the same time is an organic light emitting device comprising the coating composition or a cured product thereof. preparing a substrate;
forming a cathode or an anode on the substrate;
forming one or more organic material layers on the cathode or anode; and forming an anode or a cathode on the organic material layer, wherein the forming of the organic material layer comprises forming one or more organic material layers using the coating composition of claim 7 or a cured product thereof A method for manufacturing a light emitting device. The method according to claim 11, wherein the step of forming the organic material layer formed by using the coating composition or a cured product thereof comprises a drying step after applying the coating composition.

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