KR20190048103A - Copolymer and organic light emitting device comprising the same - Google Patents

Abstract

The present invention relates to a copolymer, a coating composition comprising the copolymer, an organic light-emitting device formed by using the coating composition, and a method of preparing the same. The present invention provides a copolymer containing a unit of chemical formula 1, a unit of chemical formula 2, and a unit of chemical formula 3; and an organic light-emitting device comprising the same. HIL/HTL materials using the copolymer of the present invention show high solubility in organic solvents and improved efficiency and lifetime.

Description

TECHNICAL FIELD [0001] The present invention relates to a copolymer and an organic light-

TECHNICAL FIELD The present invention relates to a copolymer, a coating composition comprising the copolymer, an organic light emitting device formed using the coating composition, and a method of manufacturing the same.

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic light emitting device, the organic material layer may have a multi-layer structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in the structure of such an organic light emitting device, holes are injected in the anode, electrons are injected into the organic layer in the cathode, excitons are formed when injected holes and electrons meet, When it falls back to the ground state, the light comes out.

In OLED, blue luminescence has used fluorescent phenomenon, which is superior in performance and lifetime to phosphorescence to date, and this also applies to SOLUBLE OLED. Reduction in lifetime due to triplet excitation in the blue emission of OLEDs is well known in the art. Therefore, effectively quenching the triplet excited can improve the lifetime of the OLED element. The triplet excited may predominantly be present in the EML layer but may migrate from the HTL interface to the HTL layer so that some of the HTL material can help improve performance and longevity if it can quench the triplet.

Development of new materials for such organic light emitting devices has been continuously required.

U.S. Patent Application Publication No. 2004-0251816

The present invention provides a copolymer and an organic light emitting device comprising the same.

The present invention provides a copolymer comprising a unit represented by the following formula (1), a unit represented by the following formula (2), and a unit represented by the following formula (3).

[Chemical Formula 1]

(2)

(3)

In the above Formulas 1 to 3,

은 다른 치환기, 단량체 또는 결합부에 결합되는 부위를 의미하고,

Quot; means a moiety bonded to another substituent, monomer, or binding site,

X is CR4R5 or NR7,

R1 to R7 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; 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, a thermosetting group or a photocurable group,

Ar1 and Ar2 are the same 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, or may be bonded to each other to form a ring,

Ar3 is a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted arylamine group; Or a substituted or unsubstituted heterocyclic group, a thermosetting group or a photocurable group,

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

At least one of R1, R2 and Ar3 is a thermosetting group or a photocurable group,

m 'is 1 or 2, and when m' is 2, the structures in parentheses are the same or different,

a is an integer of 0 to 4, and when a is plural, R3 is the same or different,

b is an integer of 0 to 6, and when b is plural, R6 are the same or different from each other.

Another embodiment of the present disclosure provides a coating composition comprising the copolymer and a cured product thereof.

A first electrode; A second electrode facing the first electrode; And

And at least one organic layer between the first electrode and the second electrode,

Wherein at least one of the organic material layers includes the coating composition and a cured product thereof.

Another embodiment of the present invention provides a method of manufacturing an organic light emitting device, wherein the step of forming an organic layer formed using the coating composition or the cured product thereof comprises a drying step after application of the coating composition.

The HIL / HTL material using the copolymer of the present invention has high solubility in an organic solvent and is excellent in hole transporting property in a device after film formation. In addition, it is not deformed by an additional solution process after solution coating and heat treatment process, and efficiency and lifetime can be improved.

1 shows an organic light emitting device according to an embodiment of the present invention.

Hereinafter, the present invention will be described in detail.

An embodiment of the present invention provides a copolymer comprising the unit of the formula (1), the unit of the formula (2), and the unit of the formula (3).

One embodiment of the present disclosure provides a coating composition comprising the copolymer and a cured product thereof.

One embodiment of the present disclosure includes a first electrode; A second electrode facing the first electrode; And one or more organic layers between the first electrode and the second electrode, wherein at least one of the organic layers includes the coating composition and a cured product thereof.

In one embodiment of the present invention, the step of forming using the coating composition includes a drying step after application of the coating composition.

In this specification, when a part is referred to as " including " an element, it is to be understood that it may include other elements as well, without departing from the other elements unless specifically stated otherwise.

In this specification, when a member is located on another member, it includes not only the case where the member is in contact with the other member but also the case where another member exists between the two members.

As used herein, " combination " means connecting several 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 the present specification,

Quot; means a moiety bonded to another substituent, monomer, or binding site.

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

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

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

As used herein, the term " substituted or unsubstituted " A halogen group; A nitrile group; A nitro group; Imide; Amide group; Carbonyl group; An ester group; A hydroxy group; An alkyl group; A cycloalkyl group; An alkoxy group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; An alkenyl group; Silyl group; Siloxyl group; Boron group; An amine group; Arylphosphine groups; Phosphine oxide groups; An aryl group; And a heterocyclic group, or that at least two of the substituents exemplified in the above exemplified substituents are substituted with a connected substituent, or have no substituent. For example, " a substituent to which at least two 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 carbon number of the carbonyl group is not particularly limited, but is preferably 1 to 30 carbon atoms.

In the present specification, the ester group may be substituted with an ester group oxygen in a straight chain, branched chain 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- N-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-hexyl, 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 is preferably a group having 3 to 30 carbon atoms. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, But are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, isobutyl, sec-butyl, It is not.

In this specification, the amine group is -NH ₂ ; An alkylamine group; N-arylalkylamine groups; An arylamine group; An N-arylheteroarylamine group; An N-alkylheteroarylamine group, and a heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include methylamine, dimethylamine, ethylamine, diethylamine, phenylamine, naphthylamine, biphenylamine, anthracenylamine, 9-methyl- , A diphenylamine group, an N-phenylnaphthylamine group, a ditolylamine group, an N-phenyltolylamine group, and a triphenylamine group, but are not limited thereto.

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

In the present specification, the N-arylheteroarylamine group means an amine group in which N in the amine group is substituted with an aryl group and a heteroaryl group.

In the present specification, the N-alkylheteroarylamine group means an amine group in which N in the amine group is substituted with an alkyl group and a heteroarylamine group.

In the present specification, the alkyl group in the alkylamine group, the N-arylalkylamine group, the alkylthio group, the alkylsulfoxy group and the N-alkylheteroarylamine group is the same as the alkyl group described above. Specific examples of the alkyloxy group include a methylthio group, an ethylthio group, a tert-butylthio group, a hexylthio group and an octylthio group. Examples of the alkylsulfoxy group include a mesyl group, an ethylsulfoxy group, a propylsulfoxy group, And the like, but the present invention 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 is preferably 6 to 30 carbon atoms. Specific examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, and the like, but are not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. And preferably 10 to 30 carbon atoms. Specific examples of the polycyclic aryl group include naphthyl, anthracenyl, phenanthryl, pyrenyl, perylenyl, klychenyl, fluorenyl, and the like.

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

,

,

및

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

,

,

And

And the like. 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 aforementioned aryl group. Specific examples of the aryloxy group include a phenoxy group, a p-tolyloxy group, a m-tolyloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6- trimethylphenoxy group, a p- 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 and 9-phenanthryloxy group and the arylthioxy group includes phenylthio group, 2- Methylphenylthio group, 4-tert-butylphenylthio group and the like, and examples of the arylsulfoxy group include a benzene sulfoxide group and a p-toluenesulfoxy group. However, the present invention 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 having at least two aryl groups may contain 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 non-carbon atom or hetero atom, and specifically, the hetero atom 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 is preferably 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 pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, A substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, , An isoquinolinyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, But are not limited to, phenanthroline, thiazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, phenothiazyl and dibenzofuranyl groups.

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 having 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 can be selected from the examples of the above-mentioned heterocyclic group.

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 above-mentioned heterocyclic group.

In the present specification, the copolymer further includes a unit represented by the following formula (4).

[Chemical Formula 4]

In Formula 4,

R8 is hydrogen; heavy hydrogen; A halogen group; 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, a thermosetting group or a photocurable group,

c is an integer of 0 to 4,

When c is plural, R8 are the same or different from each other, and at least one is a thermosetting group or a photocurable group.

In one embodiment of the present invention, the formula (4) is selected from the following formulas (5) to (7).

[Chemical Formula 5]

[Chemical Formula 6]

(7)

In the general formulas (5) to (7), R8 and R8 'are the same as R8 defined in the general formula (4).

According to one embodiment of the present invention, the copolymer contains one or more units represented by one of the following formulas (1-1) to (1-4).

According to one embodiment of the present invention, the copolymer includes two or more units represented by one of the following formulas (1-1) to (1-4).

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In Formulas 1-1 through 1-4,

은 다른 치환기, 단량체 또는 결합부에 결합되는 부위를 의미하고,

Quot; means a moiety bonded to another substituent, monomer, or binding site,

X and X 'are the same or different and each independently CR4R5 or NR7,

R1 to R7, and R6 'are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; 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, a thermosetting group or a photocurable group,

Ar1 and Ar2 are the same 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, or may be bonded to each other to form a ring,

Ar3 is a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted arylamine group; Or a substituted or unsubstituted heterocyclic group, a thermosetting group or a photocurable group,

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

R8 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; 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, a thermosetting group or a photocurable group,

At least one of R1, R2, R8 and Ar3 is a thermosetting group or a photocurable group,

m 'is 1 or 2, and when m' is 2, the structures in parentheses are the same or different,

a is an integer of 0 to 4, and when a is plural, R3 is the same or different,

b and b 'are an integer of 0 to 6, and when b is plural, R6 are the same or different from each other,

c is an integer of 0 to 4, and when c is plural, R8 are the same or different from each other.

According to one embodiment of the present invention, the copolymer includes one or more units represented by the following formulas (1-5) and (1-6).

[Formula 1-5]

[Chemical Formula 1-6]

In the above formulas (1-5) and (1-6)

R1 to R8, R6 ', Ar1 to Ar3, L1, a to c, and m' are as defined in the above formulas 1-1 to 1-4,

o to r are molar ratios of the respective units,

o is a molar ratio of from 0.05 to 0.95,

p is a molar ratio of 0.05 to 0.95,

q is a molar ratio of from 0.05 to 0.95,

and r is a molar ratio of 0.05 to 0.95.

In one embodiment of the present disclosure. X and X 'are the same or different from each other, and each independently CR4R5 or NR7

In one embodiment of the present disclosure, R3, R6 and R6 'are hydrogen.

In one embodiment of the present invention, R 1 and R 2 are the same or different and each independently represent a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

In one embodiment of the present specification, R 1 and R 2 are substituted or unsubstituted, linear or branched alkyl groups having 1 to 30 carbon atoms.

In one embodiment of the present invention, R 1 and R 2 are the same or different and each independently represents a linear or branched alkyl group having 1 to 30 carbon atoms.

In one embodiment of the present invention, R 4 and R 5 are the same or different and each independently represent a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

In one embodiment of the present invention, R 4 and R 5 are the same or different and each independently represents a substituted or unsubstituted, linear or branched alkyl group having 1 to 20 carbon atoms.

In one embodiment of the present invention, R4 and R5 are the same or different and each independently represents a straight or branched alkyl group having 1 to 20 carbon atoms.

In one embodiment of the present specification, R7 is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

In one embodiment of the present specification, R7 is a substituted or unsubstituted, linear or branched alkyl group having 1 to 20 carbon atoms.

In one embodiment of the present invention, R7 is a straight or branched alkyl group having 1 to 20 carbon atoms.

In one embodiment of the present specification, R8 and R8 'are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; 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, a thermosetting group or a photocurable group,

In one embodiment of the present specification, R8 and R8 'are the same or different from each other, and each independently hydrogen; heavy hydrogen; A 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 formulas.

Ri to Riv are the same or different from each other, and each independently hydrogen; heavy hydrogen; A 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 alkoxysilyl group, or a substituted or unsubstituted arylene group,

t is an integer of 0 to 4, and when t is 2 or more, Riv is equal to or different from each other,

s is an integer of 0 to 5, and when s is plural, Riii are the same or different from each other.

In one embodiment of the present invention, R8 and R8 'are the same or different from each other, and are each independently a thermosetting or photocurable group.

In one embodiment of the present invention, R8 and R8 'are the same or different alkoxy groups each independently substituted with an aryl group substituted with an alkenyl group or unsubstituted.

In one embodiment of the present invention, R8 and R8 'are the same or different and each independently represents an alkoxy group substituted or unsubstituted with an aryl group having 6 to 20 carbon atoms substituted with an alkenyl group having 1 to 10 carbon atoms.

In one embodiment of the present specification, R8 and R8 'are the same or different and each independently represent an aryl group having 6 to 20 carbon atoms and substituted with an alkenyl group having 1 to 10 carbon atoms, Lt; / RTI >

In one embodiment of the present invention, R8 and R8 'are the same or different and each independently represent an alkoxy group having 1 to 10 carbon atoms which is substituted or unsubstituted with a styrene group.

In one embodiment of the present invention, R8 and R8 'are the same or different and each independently a methoxy group substituted or unsubstituted with a styrene group.

In one embodiment of the present invention, Ar1 and A2 are the same or different and are 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 one embodiment of the present invention, Ar1 and A2 are the same or different and are each independently a direct bond; A substituted or unsubstituted monocyclic arylene group; Or a substituted or unsubstituted polycyclic arylene group.

In one embodiment of the present invention, Ar1 and A2 are the same or different and are each independently a direct bond; A substituted or unsubstituted monocyclic C 6-20 arylene group; Or a substituted or unsubstituted polycyclic arylene group having 10 to 20 carbon atoms.

In one embodiment of the present invention, Ar1 and A2 are the same or different and each independently an arylene group having 6 to 20 carbon atoms.

In one embodiment of the present invention, Ar1 and A2 are the same or different and each independently a monocyclic arylene group having 6 to 20 carbon atoms.

In one embodiment of the present invention, Ar1 and A2 are the same or different and each independently a polycyclic arylene group having 10 to 20 carbon atoms.

In one embodiment of the present invention, Ar1 and A2 are the same or different from each other, and each independently represents a phenylene group; Biphenylene group; A terphenylene group; A naphthalenyl group; Phenanthrenylene group; Or an anthracenylene group.

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

In one embodiment of the present specification, Ar1 and A2 combine with each other to form a ring.

In one embodiment of the present invention, Ar3 is a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted arylamine group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, Ar3 is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

In one embodiment of the present specification, Ar3 is a substituted or unsubstituted straight chain alkyl group having 1 to 20 carbon atoms.

In one embodiment of the present specification, Ar 3 is a substituted or unsubstituted, branched alkyl group having 1 to 20 carbon atoms.

In one embodiment of the present specification, Ar 3 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; A substituted or unsubstituted arylamine group; Or a substituted or unsubstituted heterocyclic group having 3 to 20 carbon atoms.

In one embodiment of the present specification, Ar3 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, Ar3 is a substituted or unsubstituted amine having 6 to 20 carbon atoms substituted with a monocyclic or polycyclic aryl group.

In one embodiment of the present specification, Ar 3 is a substituted or unsubstituted N, O, or S-containing heterocyclic group having 3 to 20 carbon atoms.

In one embodiment of the present specification, Ar3 is a substituted or unsubstituted N-containing heterocyclic group having 3 to 20 carbon atoms.

In one embodiment of the present invention, Ar3 is a carbazole group substituted or unsubstituted with a styrene group or a phenyl group.

In one embodiment of the present specification, Ar3 is a carbazol group substituted or unsubstituted with a phenyl group.

In one embodiment of the present disclosure, L1 is a direct bond; A substituted or unsubstituted arylene group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms.

In one embodiment of the present disclosure, L1 is a direct bond; A substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 20 carbon atoms.

In one embodiment of the present specification, L1 is a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

In one embodiment of the present disclosure, L1 is a direct bond; Or a phenylene group.

In one embodiment of the present invention, at least one of R1, R2, R8, and Ar3 is a thermosetting group or a photocurable group.

In one embodiment of the present specification, the copolymer includes any one or more selected from the following structures.

In the above structural formulas, the definitions of o to r are as defined above.

According to one embodiment of the present disclosure, o is a molar ratio of 0.5 to 0.9.

According to one embodiment of the present disclosure, p is a molar ratio of 0.1 to 0.5.

According to one embodiment of the present disclosure, q is a molar ratio of 0.1 to 0.5.

According to one embodiment of the present disclosure, r is a molar ratio of 0.5 to 0.9.

According to one embodiment of the present invention, o has a molar ratio of 0.5 to 0.7, p is 0.1 to 0.3, and q has a molar ratio of 0.1 to 0.3.

According to one embodiment of the present invention, the r is 0.5 to 0.7, p is 0.1 to 0.3, and q is a molar ratio of 0.1 to 0.3.

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

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

According to one embodiment of the present disclosure, the copolymer is any one of the following structures.

The triplet excited by the naphthalene structure contained in the units constituting the copolymer contributes to performance and life span improvement by quenching.

According to one embodiment of the present disclosure, the end of the copolymer may be hydrogen, or a substituted or unsubstituted aryl group.

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

According to one embodiment of the present invention, the end of the copolymer may be hydrogen or an aryl group substituted or unsubstituted with a straight or branched alkyl group having 1 to 10 carbon atoms.

According to one embodiment of the present invention, the end of the copolymer may be hydrogen or an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with a straight or branched alkyl group having 1 to 10 carbon atoms.

According to one embodiment of the present disclosure, the end of the copolymer may be hydrogen, a phenyl group, or a 4-tert-butylphenyl group.

According to one embodiment of the present disclosure, the coating composition comprises the copolymer.

According to one embodiment of the present disclosure, the coating composition comprises the copolymer in an amount ranging from 0.01 to 30% by weight.

According to one embodiment of the present disclosure, the coating composition comprises the copolymer in an amount ranging from 0.1 to 15% by weight.

According to one embodiment of the present disclosure, the coating composition comprises the copolymer in an amount ranging from 0.1 to 10% by weight.

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

The organic light emitting device of the present invention can be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer is formed using the coating composition comprising 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 the present invention is not limited thereto.

1 shows an organic light emitting device in which a first electrode 2, an organic material layer 3 including the coating composition and a cured product thereof, a light emitting layer 4 and a second electrode 5 are sequentially stacked on a substrate 1 Structure is illustrated.

In one embodiment of the present invention, the organic compound layer including the coating composition and the cured product thereof includes at least one of an electron injecting layer, an electron transporting layer, and a layer simultaneously performing electron injection and electron transporting, and at least one of the layers Layer may comprise the coating composition and a cured product thereof.

In one embodiment of the present invention, the organic compound layer including the coating composition and the cured product thereof includes at least one of a hole injecting layer, a hole transporting layer, and a layer simultaneously transporting holes and holes, and at least one of the layers Layer may comprise the coating composition and a cured product thereof.

For example, the organic light emitting device according to the present invention may be formed by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to form a metal oxide or a metal oxide having conductivity on the substrate, A hole transporting layer, a light emitting layer, an organic material layer including an electron transporting layer, and an organic material layer containing the copolymer are formed on the anode, and a material which can be used as a cathode is deposited thereon. . In addition to such a method, an organic light emitting device may be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.

As the anode material, a material having a large work function is preferably used so that hole injection can be smoothly conducted into the organic material layer. Specific examples of the cathode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methyl compounds), poly [3,4- (ethylene-1,2-dioxy) compounds] (PEDT), polypyrrole and polyaniline.

The negative electrode 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; Layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

As the hole injecting material, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene , An anthraquinone, and a conductive polymer of polyaniline and a poly-compound, but the present invention is not limited thereto.

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

The light emitting material is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Polymers of poly (p-phenylenevinylene) (PPV) series; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

The light emitting layer may include a host material and a dopant material. The host material is a condensed aromatic ring derivative or a heterocyclic compound. Specific examples of the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds. Examples of the heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

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

The organic light emitting device of the present invention can be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer is formed using the coating composition comprising the copolymer.

For example, the organic light emitting device of the present specification can be manufactured by sequentially laminating an anode, an organic layer, and a cathode on a substrate. At this time, a metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate by a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to form an anode Forming an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer and an electron transporting layer thereon, and then depositing a material usable as a cathode thereon. In addition to such a method, an organic light emitting device can be formed by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

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

Specifically, in one embodiment of the present disclosure, there is provided a method comprising: preparing a substrate; Forming a cathode or an anode on the substrate; Forming at least one organic material layer on the cathode or the 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 at least one layer of the organic material layer using the coating composition may include a coating step followed by a drying step. If necessary, the drying step may include a curing step.

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

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

In the state of the present specification, the printing method includes, but is not limited to, ink jet printing, nozzle printing, offset printing, transfer printing, or screen printing.

Since the coating composition according to one embodiment of the present invention has a structural characteristic and is suitable for a solution process, the coating composition can be formed by a printing method, so that there is an economical effect in time and cost in manufacturing a device.

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

In one embodiment of the present disclosure, the step of heat-treating or vacuum-drying may comprise a curing step.

In one embodiment of the present invention, the polymer binder is preferably one that does not extremely inhibit charge transport, and that does not strongly absorb visible light. Examples of the polymeric binder include poly (N-vinylcarbazole), polyaniline and derivatives thereof, polythiophene and derivatives thereof, poly (p-phenylenevinylene) and derivatives thereof, poly (2,5-thienylenevinylene) A derivative thereof, a polycarbonate, a polyacrylate, polymethyl acrylate, polymethyl methacrylate, polystyrene, polyvinyl chloride, polysiloxane and the like.

Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specific examples of the aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, and examples thereof include pyrene, anthracene, chrysene, and peripherrhene having an arylamino group. Examples of the styrylamine compound include substituted or unsubstituted Wherein at least one aryl vinyl group is substituted with at least one aryl vinyl group, and at least one substituent selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group is substituted or unsubstituted. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like. Examples of the metal complex include iridium complex, platinum complex, and the like, but are not limited thereto.

The electron transporting material is a layer that transports electrons from the electron injecting layer to the electron transporting layer and transports electrons from the electron injecting layer to the light emitting layer. The electron transporting material is a material capable of transferring electrons from the cathode to the light emitting layer. Is suitable. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq3; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transporting layer can be used with any desired cathode material as used according to the prior art. In particular, an example of a suitable cathode material is a conventional material having a low work function followed by an aluminum layer or a silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.

The electron injection layer is a layer for injecting electrons from an electrode and has an ability to transport electrons and has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, A compound which prevents migration to a layer and is excellent in a thin film forming ability is preferable. Specific examples thereof include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, A complex compound and a nitrogen-containing five-membered ring derivative, 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- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8- hydroxyquinolinato) gallium, bis (10- Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8- quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, and the like, But is not limited thereto.

The hole blocking layer is a layer which prevents the cathode from reaching the hole, and can be generally formed under the same conditions as the hole injecting layer. Specific examples thereof include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes and the like.

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

The method for producing the copolymer and the production of the organic light emitting device using the same will be described in detail in the following examples. However, the following examples are intended to illustrate the present invention and the scope of the present invention is not limited thereto.

Production Example 1. Preparation of Copolymer 1

2,2 '- (9,9-dioctyl-9H-fluorene-2,7-diyl) bis (4,4,5,5-tetramethyl-1,3,2-dioxaboroline) , 3.11 mmol) and 4-bromo-N- (4-bromophenyl) -N- (4- (9- (0.546 g, 0.622 mmol), 4,4 '- (((2,5-dibromo-1, Bis (methylene)) bis (vinylbenzene) (0.310 g, 0.622 mmol) was dissolved in 30 mL of toluene in 100 mL of RBF, and 20 wt% aq. Et4NOH (10 mL) was added, the temperature was raised to 90 ° C, and the mixture was stirred for 30 minutes. Tetrakis triphenylphosphine palladium (0) (89 mg) was dissolved in 5 mL of toluene, and the mixture was stirred for 48 hours. The mixture was cooled to room temperature, precipitated in methanol, filtered, washed with methanol, water, ethanol and hexane, and dissolved in methylene chloride. Charcoal, CPS-T and MgSO4 were added and stirred at room temperature for 30 minutes. The stirred mixture was passed through silica treated with triethylamine, and the methylene chloride was removed. The residue was dissolved in a small amount of toluene, adsorbed on silica treated with triethylamine, loaded on the column, washed with hexane The toluene was dissolved again in toluene to remove toluene, and a part of it was left to precipitate in methanol, followed by filtration and drying.

The number average molecular weight is 35,000 g / mol and the weight average molecular weight is 75,200 g / mol.

Production Example 2. Preparation of Copolymer 2

2,2 '- (9,9-dioctyl-9H-fluorene-2,7-diyl) bis (4,4,5,5-tetramethyl-1,3,2-dioxaboroline) , 3.11 mmol), 3,6-dibromo-9- (heptadecan-9-yl) -9H- carbazole (1.052 g, 1.87 mmol), 2,6-dibromo-3,7- (2-oxydodecyloxy) naphthalene (0.546 g, 0.622 mmol), 4,4 '- (((2,5- dibromo- ) Bis (vinylbenzene) (0.310 g, 0.622 mmol) was dissolved in 30 mL of toluene in 100 mL of RBF, and 20 wt% aq. Et4NOH (10 mL) was added, the temperature was raised to 90 ° C, and the mixture was stirred for 30 minutes. Tetrakis triphenylphosphine palladium (0) (89 mg) was dissolved in 5 mL of toluene, and the mixture was stirred for 48 hours. The mixture was cooled to room temperature, precipitated in methanol, filtered, washed with methanol, water, ethanol and hexane, and dissolved in methylene chloride. Charcoal, CPS-T and MgSO4 were added and stirred at room temperature for 30 minutes. The stirred mixture was passed through silica treated with triethylamine, and the methylene chloride was removed. The residue was dissolved in a small amount of toluene, adsorbed on silica treated with triethylamine, loaded on the column, washed with hexane The toluene was dissolved again in toluene to remove toluene, and a part of it was left to precipitate in methanol, followed by filtration and drying.

The number average molecular weight is 49,000 g / mol and the weight average molecular weight is 86,600 g / mol.

Production Example 3. Preparation of comparative copolymer 1

2,2 '- (9,9-dioctyl-9H-fluorene-2,7-diyl) bis (4,4,5,5-tetramethyl-1,3,2-dioxaboroline) , 3.11 mmol), 4-bromo-N- (4-bromophenyl) -N- (4- (9- (Methylene)) bis (vinylbenzene) (0.311 g, 0.622 mmol) was added to 100 mL of RBF, and a solution of 4,4 '- ((2,5- dibromo-1,4- After dissolving in 30 mL of toluene, 20 wt% aq. Et4NOH (10 mL) was added, the temperature was raised to 90 ° C, and the mixture was stirred for 30 minutes. Tetrakis triphenylphosphine palladium (0) (89 mg) was dissolved in 5 mL of toluene, and the mixture was stirred for 48 hours. The mixture was cooled to room temperature, precipitated in methanol, filtered, washed with methanol, water, ethanol and hexane, and dissolved in methylene chloride. Charcoal, CPS-T and MgSO4 were added and stirred at room temperature for 30 minutes. The stirred mixture was passed through silica treated with triethylamine, and the methylene chloride was removed. The residue was dissolved in a small amount of toluene, adsorbed on silica treated with triethylamine, loaded on the column, washed with hexane The toluene was dissolved again in toluene to remove toluene, and a part of it was left to precipitate in methanol, followed by filtration and drying.

The number average molecular weight is 41,000 g / mol and the weight average molecular weight is 62,200 g / mol.

Production Example 4. Preparation of comparative copolymer 2

2,2 '- (9,9-dioctyl-9H-fluorene-2,7-diyl) bis (4,4,5,5-tetramethyl-1,3,2-dioxaboroline) , 3.11 mmol), 4-bromo-N- (4-bromophenyl) -N- (4- (9- 2,6-dibromo-3,7-bis ((2-oxydodecyl) oxy) naphthalene (0.546 g, 0.622 mmol) was added to 100 mL of RBF and dissolved in 30 mL of toluene. Et4NOH (10 mL) was added, the temperature was raised to 90 ° C, and the mixture was stirred for 30 minutes. Tetrakis triphenylphosphine palladium (0) (89 mg) was dissolved in 5 mL of toluene, and the mixture was stirred for 48 hours. The mixture was cooled to room temperature, precipitated in methanol, filtered, washed with methanol, water, ethanol and hexane, and dissolved in methylene chloride. Charcoal, CPS-T and MgSO4 were added and stirred at room temperature for 30 minutes. The stirred mixture was passed through silica treated with triethylamine, and the methylene chloride was removed. The residue was dissolved in a small amount of toluene, adsorbed on silica treated with triethylamine, loaded on the column, washed with hexane The toluene was dissolved again in toluene to remove toluene, and a part of it was left to precipitate in methanol, followed by filtration and drying.

The number average molecular weight is 32,000 g / mol and the weight average molecular weight is 52,700 g / mol.

Example 1

The glass substrate on which ITO (indium tin oxide) was deposited to a thickness of 1500 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. After the ITO was washed for 30 minutes, ultrasonic washing was repeated 10 times with distilled water twice. After the distilled water was washed, ultrasonic washing was performed with a solvent of isopropyl alcohol and acetone for 30 minutes each, and the substrate was transported to a glove box.

The following compounds A and B were mixed at a weight ratio of 7: 3 on the prepared ITO transparent electrode, and the solution was dissolved in cyclohexanone in a concentration of 2 wt%. This was heated at 220 캜 for 30 minutes in a nitrogen atmosphere to form a hole injection layer. Thereafter, the copolymer 1 was dissolved in toluene at a concentration of 0.7 wt%, spin-coated on the hole injection layer to form a film having a thickness of 200 ANGSTROM, and the mixture was heated at 200 DEG C for 30 minutes under a nitrogen atmosphere to form a hole transport layer. Thereafter, the compound was transferred to a vacuum evaporator, and then Compound 2 and Compound 3 shown below were vacuum deposited on the hole transport layer to a thickness of 300 Å at a concentration of 8 wt% to form a light emitting layer. The following compound 4 was vacuum deposited on the light emitting layer to a thickness of 200 Å to form an electron injection and transport layer. Aluminum was sequentially deposited on the electron injecting and transporting layer to a thickness of 12 Å and a thickness of 2000 Å to form a cathode.

 [Compound A]

[Compound B]

Was maintained at the deposition rate 0.4 ~ 0.7Å / sec for organic material in the above process, the cathode of LiF was 0.3Å / sec, aluminum was deposited at a rate of 2Å / sec, the degree of vacuum upon deposition 2x10 ^-7 ~ 5x10 ^{- 8} torr was maintained.

Thereafter, sealing was performed by bonding the sealing glass and the glass substrate to the glass using a photo-curable epoxy resin, to produce an organic EL device having a multilayer structure. Subsequent operations were performed at room temperature (25 캜) in the atmosphere.

Example 2

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

Comparative Example 1

An organic light emitting device was prepared in the same manner as in Example 1, except that the hole transport layer in Example 1 was replaced by Comparative Copolymer 1 instead of Copolymer 1.

Comparative Example 2

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

Table 2 shows the results of measuring the driving voltage and efficiency at an electric current density of 10 mA / cm < ² > in the organic light emitting device manufactured by the above method.

Example Hole transport layer The driving voltage (V) Current efficiency (cd / A) EQE (%) Life time
(95%, h) Example 1 Copolymer 1 4.04 7.09 7.78 36 Example 2 Copolymer 2 4.17 5.48 5.98 33 Comparative Example 1 Comparative Copolymer 1 4.45 3.34 3.59 16 Comparative Example 2 Comparative Copolymer 2 5.08 0.60 0.43 13

In the case of using the copolymer containing the general formulas (1) to (3) of the present invention, the polymer which is connected to the main chain of the polymer at positions 2 and 6 of naphthalene is used as HIL to HTL.

In this case, since the triplet excited by the naphthalene unit is quenched, the effect and the lifetime of the comparative copolymer 1 without naphthalene are better than those without the naphthalene. The results of comparison between Comparative Example 1 used as a transport layer and Copolymers 1 and 2 containing the above Formulas 1 to 3 are supported.

When the EML layer coating is not performed, the HTL layer coated on the solvent of the EML solution dissolves in the coating of the EML layer, which results in a problem of interfacial problems, bonding of the HIL layer and the EML layer, The life span is lowered.

This is confirmed from the fact that Comparative Example 2 in which the comparative copolymer 2 containing no curing agent was used as a hole transport layer has a remarkably low performance and life.

1: substrate
2: first electrode
3: organic layer
4: light emitting layer
5: Second electrode

Claims (12)

A copolymer comprising a unit of the following formula (1), a unit of the following formula (2), and a unit of the following formula
[Chemical Formula 1]

(2)

(3)

In the above Formulas 1 to 3,

Quot; means a moiety bonded to another substituent, monomer, or binding site,
X is CR4R5 or NR7,
R1 to R7 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; 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, a thermosetting group or a photocurable group,
Ar1 and Ar2 are the same 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, or may be bonded to each other to form a ring,
Ar3 is a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted arylamine group; Or a substituted or unsubstituted heterocyclic group, a thermosetting group or a photocurable group,
L1 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
At least one of R1, R2 and Ar3 is a thermosetting group or a photocurable group,
m 'is 1 or 2, and when m' is 2, the structures in parentheses are the same or different,
a is an integer of 0 to 4, and when a is plural, R3 is the same or different,
b is an integer of 0 to 6, and when b is plural, R6 are the same or different from each other. The copolymer according to claim 1, wherein the copolymer further comprises a unit represented by the following formula (4):
[Chemical Formula 4]

In Formula 4,
R8 is hydrogen; heavy hydrogen; A halogen group; 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, a thermosetting group or a photocurable group,
c is an integer of 0 to 4,
When c is plural, R8 are the same or different from each other, and at least one is a thermosetting group or a photocurable group. 3. The compound of claim 2, wherein R8 is hydrogen; heavy hydrogen; A 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 formulas:

In the above formula,
Ri to Riv are the same or different from each other, and each independently hydrogen; heavy hydrogen; A 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 alkoxysilyl group, or a substituted or unsubstituted arylene group,
t is an integer from 0 to 4,
When t is 2 or more, Riv is the same or different from each other,
s is an integer of 0 to 5,
When s is plural, Riii are the same or different from each other. The method according to claim 1,
Wherein the copolymer comprises one or more units represented by one of the following formulas (1-1) to (1-4):
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In Formulas 1-1 through 1-4,

Quot; means a moiety bonded to another substituent, monomer, or binding site,
X and X 'are the same or different and each independently CR4R5 or NR7,
R1 to R7, and R6 'are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; 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, a thermosetting group or a photocurable group,
Ar1 and Ar2 are the same 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, or may be bonded to each other to form a ring,
Ar3 is a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted arylamine group; Or a substituted or unsubstituted heterocyclic group, a thermosetting group or a photocurable group,
L1 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
R8 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; 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, a thermosetting group or a photocurable group,
At least one of R1, R2, R8 and Ar3 is a thermosetting group or a photocurable group,
m 'is 1 or 2, and when m' is 2, the structures in parentheses are the same or different,
a is an integer of 0 to 4, and when a is plural, R3 is the same or different,
b and b 'are an integer of 0 to 6, and when b is plural, R6 are the same or different from each other,
c is an integer of 0 to 4, and when c is plural, R8 are the same or different from each other. The copolymer according to claim 1, wherein the copolymer comprises at least one selected from the following structures:

Wherein o to r are molar ratios of the respective units,
o is a molar ratio of from 0.05 to 0.95,
p is a molar ratio of 0.05 to 0.95,
q is a molar ratio of from 0.05 to 0.95,
and r is a molar ratio of 0.05 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 a copolymer according to any one of claims 1 to 6. A first electrode;
A second electrode facing the first electrode; And
And at least one organic layer between the first electrode and the second electrode,
Wherein at least one of the organic material layers comprises the coating composition of claim 7 or a cured product thereof. The method of claim 8,
Wherein the organic material layer includes a hole transporting layer, a hole injecting layer, or a layer simultaneously transporting holes and injecting holes,
Wherein the hole transporting layer, the hole injecting layer, or the layer simultaneously transporting the hole and the hole injecting layer comprises the coating composition or the cured product thereof. The method of claim 8,
Wherein the organic material layer includes an electron injection layer, an electron transport layer, or a layer simultaneously performing electron injection and electron transport,
Wherein the electron injecting layer, the electron transporting layer, or the layer simultaneously injecting electrons and electron transporting comprises the coating composition or a cured product thereof. Preparing a substrate;
Forming a cathode or an anode on the substrate;
Forming at least one organic material layer on the cathode or the anode; And forming an anode or a cathode on the organic material layer, wherein the forming of the organic material layer includes forming at least one organic material layer using the coating composition of claim 7 or a cured product thereof. A method of manufacturing a light emitting device. [Claim 12] The method of claim 11, wherein the step of forming the organic compound layer using the coating composition or the cured product thereof comprises a drying step after application of the coating composition.

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