KR20230115617A - Low temperature curable photosensitive resin composition and cured flim prepared therefrom - Google Patents

Abstract

[화학식 2]

(상기 화학식 1 및 2에서, L₁ 내지 L₃, X₁, X₂, A 및 B는 본 명세서에 기재한 바와 같다.)The present invention relates to a photosensitive resin composition including a polymer including a repeating unit represented by Formula 1 below and a compound represented by Formula 2 below. Specifically, the photosensitive resin composition according to one embodiment can be cured at a low temperature and can provide a cured film capable of realizing precise patterns and excellent optical properties.
[Formula 1]

[Formula 2]

(In Formulas 1 and 2, L ₁ to L ₃ , X ₁ , X ₂ , A and B are as described herein.)

Description

Low temperature curable photosensitive resin composition and cured film prepared therefrom

The present invention relates to a low-temperature curable photosensitive resin composition and a cured film prepared therefrom.

Organic light emitting diodes are not only advantageous in terms of power consumption because they can be driven at low voltage, but also have excellent color implementation, response speed, viewing angle, contrast ratio, etc., and are in the limelight as next-generation displays. However, most of the light generated in the light emitting layer of the organic light emitting device is trapped inside and does not contribute to the light output, and there is a limit in that the light extraction efficiency is only about 20%, so improving the light extraction efficiency of the organic light emitting device is very important. It is a research project.

A light extraction material for improving the light extraction efficiency of an organic light emitting device should have excellent optical properties such as high refractive index and high transparency, as well as form hole patterns of several micrometers. Accordingly, the photosensitive resin composition capable of photo-patterning has been in the limelight as a light extraction material for organic light emitting devices, but recently, due to the high performance of devices, it is possible to manufacture organic films capable of realizing more precise patterns and excellent optical properties. It is necessary to develop a photosensitive resin composition.

Moreover, recently, as light weight, slimness, and flexibility of display devices are considered important, existing glass materials are being replaced with plastic materials. Accordingly, since a material having sufficient curing degree, excellent mechanical properties, and chemical resistance is required even in a low-temperature process, the performance requirements of photosensitive resin compositions for application to next-generation display devices are gradually increasing.

That is, there is a need for a photosensitive resin composition for forming a cured film capable of ensuring a sufficient degree of curing even at a low temperature and at the same time satisfying both the realization of a precise pattern and excellent optical properties.

Korean Registered Patent Publication No. 11399281 (2009.01.08)

An object of the present invention is to provide a photosensitive resin composition capable of low-temperature curing and at the same time implementing a precise pattern, and capable of preparing a cured film having excellent refractive index and chemical resistance.

In addition, another object of the present invention is to provide a cured film applicable as a next-generation display device material using the photosensitive resin composition.

In addition, another object of the present invention is to provide an organic light emitting device having significantly improved light extraction efficiency by employing the cured film.

One aspect of the present invention provides a photosensitive resin composition comprising a polymer including a repeating unit represented by Formula 1 below and a compound represented by Formula 2 below.

[Formula 1]

[Formula 2]

(In Chemical Formulas 1 and 2,

L ₁ is (C1-C20)alkylene, (C6-C20)arylene or (C3-C20)heteroarylene;

L ₂ and L ₃ are each independently a single bond, (C1-C20)alkylene, (C6-C20)arylene or (C3-C20)heteroarylene, and -CH ₂ - of the alkylene is -O- , -S-, -NH-, -C(=O)-, or a combination thereof;

X ₁ and X ₂ are each independently -O- or -NH-;

A is or It is one of four groups selected from;

L _a is a single bond, -O-, -C(=O)-, -S-, -SO ₂ -, (C1-C20)alkylene, (C6-C20)arylene, (C3-C20)heteroaryl may be rene or a combination thereof, and the alkylene may be further substituted with one or more selected from (C1-C10)alkyl and halo(C1-C10)alkyl;

R ₁ to R ₃ are each independently (C1-C10)alkyl or halo(C1-C10)alkyl;

p is an integer from 1 to 10;

a to c are each independently an integer of 0 to 2;

B is (C1-C20)alkylene, (C6-C20)arylene, (C3-C20)heteroarylene, (C3-C20)cycloalkylene, (C3-C20)heterocycloalkylene or ego;

Ar ₁ and Ar ₂ are each independently (C6-C20)arylene or (C3-C20)heteroarylene;

L _b is a single bond or (C1-C10)alkylene;

q is an integer from 1 to 10;

The alkylene, arylene, heteroarylene, cycloalkylene and heterocycloarylene of B and the arylene and heteroarylene of Ar ₁ and Ar ₂ are (C1-C10)alkyl, -NCO, -OCN, ( It may be further substituted with one or more selected from C6-C12) aryl and (C1-C10) alkoxy.)

The repeating unit represented by Chemical Formula 1 may be represented by Chemical Formula 3 below.

[Formula 3]

(In Formula 3,

L ₁ is (C1-C20)alkylene or (C6-C20)arylene;

L ₁₁ to L ₁₄ are each independently (C1-C20)alkylene, (C6-C20)arylene or (C3-C20)heteroarylene;

X ₁ and X ₂ are each independently -O- or -NH-;

The definition of A is the same as the definition in Formula 1 of claim 1.)

The A may be a tetravalent group selected from the following structures.

(In the above structural formula,

L ₂₁ to L ₂₄ are each independently a single bond, -O-, -C(=O)-, -S-, -SO ₂ - or (C1-C7)alkylene, and the alkylene is (C1-C7 ) may be further substituted with one or more selected from alkyl and halo (C1-C7) alkyl;

R ₁ to R ₃ are each independently (C1-C7)alkyl or halo(C1-C7)alkyl;

a to c are each independently an integer of 0 to 2.)

L ₂₁ and L ₂₂ are each independently a single bond, -O-, -C(=O)-, or -CR _a R _b -; L ₂₃ and L ₂₄ are each independently -O- or -S-; R _a and R _b may each independently be (C1-C3)alkyl or halo(C1-C3)alkyl.

The repeating unit represented by Chemical Formula 1 may be represented by Chemical Formula 4 below.

[Formula 4]

(In Chemical Formula 4,

L ₁ is (C1-C7)alkylene or (C6-C12)arylene;

L ₁₁ to L ₁₄ are each independently (C1-C7)alkylene;

L ₃₁ is a single bond, -O-, -C(=O)- or -C(CF ₃ ) ₂ -;

p is an integer from 1 to 5.)

The repeating unit represented by Chemical Formula 1 may be represented by Chemical Formula 5 below.

[Formula 5]

(In Formula 5,

L ₃₁ is a single bond, -O-, -C(=O)- or -C(CF ₃ ) ₂ -.)

The repeating unit represented by Chemical Formula 1 may be selected from the following structures.

The weight average molecular weight of the polymer according to one aspect may be 2,000 g / mol to 10,000 g / mol.

The B may be selected from the following structure.

(In the above structure,

R ₁₁ to R ₁₆ are each independently (C1-C10)alkyl, -NCO, -OCN, (C6-C12)aryl, and (C1-C10)alkoxy;

d to i are each independently an integer of 0 to 4;

D ₁ to D ₃ are each independently a single bond or (C1-C10)alkylene;

m is an integer from 1 to 10.)

The compound represented by Formula 2 may be represented by Formula 11 or Formula 12 below.

[Formula 11]

[Formula 12]

(In Chemical Formulas 11 and 12,

D ₁₁ to D ₁₃ are each independently a single bond or (C1-C5)alkylene;

R ₁₅ is (C1-C5)alkyl, -NCO or -OCN;

m is an integer from 1 to 10.)

The compound represented by Formula 2 may be selected from the following structures.

(In the above structure, m is an integer from 1 to 10.)

The compound represented by Chemical Formula 2 and the polymer may be included in a weight ratio of 1:1 to 1:10.

The photosensitive resin composition according to an aspect may further include a photopolymerizable monomer, a photoinitiator, and a thermal curing agent.

The photopolymerizable monomer may be a multifunctional monomer having an ethylenically unsaturated bond.

The photoinitiator may be one or two or more selected from acetophenone-based compounds, benzophenone-based compounds, triazine-based compounds, benzoin-based compounds, imidazole-based compounds, xanthone-based compounds, phosphine-based compounds, and oxime-based compounds.

The heat curing agent may be one or two or more selected from an imidazole-based compound, a dihydrazide-type compound, and an amine-based compound.

In addition, one aspect of the present invention provides a cured film obtained by curing the photosensitive resin composition.

In addition, one aspect of the present invention provides an organic electronic device including the cured film.

As the photosensitive resin composition according to one aspect of the present invention includes a compound combination having a specific structure, sufficient curing degree and mechanical properties can be secured even at low temperature curing. At the same time, since photo-patterning is possible, a separate etching process is not required, and precise patterns can be implemented with excellent sensitivity and developability.

Specifically, the photosensitive resin composition according to one aspect can be cured at a low temperature and is applicable to plastic substrates, and since an additional etching process is not required, it is possible to reduce production cost and improve productivity, and to prevent damage to surrounding materials due to the etching process. It can be prevented.

In addition, the cured film prepared from the photosensitive resin composition according to one aspect has excellent optical properties such as refractive index and can be applied as a light extraction material for an organic light emitting device.

In addition, the organic light emitting device employing the cured film according to one aspect may not only improve light extraction efficiency, reduce power consumption, and implement excellent lifespan characteristics.

Unless defined otherwise herein, all technical and scientific terms have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. The terms used in the description herein are merely to effectively describe specific embodiments and are not intended to limit the invention.

The singular form used herein may be intended to include the plural form as well, unless the context dictates otherwise.

Further, as used herein, numerical ranges include lower and upper limits and all values within that range, increments logically derived from the shape and breadth of the defined range, all values defined therebetween, and the upper limit of the numerical range defined in a different form. and all possible combinations of lower bounds. Unless otherwise specifically defined herein, values outside the numerical range that may occur due to experimental errors or rounding of values are also included in the defined numerical range.

The term "includes" in the present specification is an open description having the same meaning as expressions such as "includes", "includes", "has" or "characterized by", and elements not additionally listed, No materials or processes are excluded.

As used herein, the term “polymer” may include oligomers, and includes homopolymers and copolymers, wherein the copolymers include alternating polymers, block copolymers, random copolymers, branched copolymers, crosslinked copolymers, or these It may be all inclusive.

As used herein, the term "alkyl" is an organic radical derived from an aliphatic hydrocarbon by removing one hydrogen, and may include both straight-chain and branched forms. Examples include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, pentyl, hexyl, ethylhexyl, and the like.

As used herein, the term "alkylene" is a divalent organic radical derived from an aliphatic hydrocarbon by removing two hydrogens, and may include both straight-chain and branched forms. Examples include, but are not limited to, methylene, ethylene, propylene, isopropylene, butylene, isobutylene, t-butylene, pentylene, hexylene, octylene, nonylene, and the like.

As used herein, the term "alkoxy" is represented by *-O-alkyl, where alkyl has the same definition as above. Examples of the alkoxy include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, t-butoxy, and the like.

As used herein, the term "aryl" is an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen, either singly or fused, containing preferably 4 to 7, preferably 5 or 6, ring atoms in each ring. It includes a ring system and may even include a form in which a plurality of aryls are connected by single bonds. Examples include, but are not limited to, phenyl, naphthyl, biphenyl, terphenyl, and the like.

As used herein, the term "arylene" is an aromatic ring divalent organic radical derived from an aromatic hydrocarbon, and is a single or fused ring system containing 4 to 7, preferably 5 or 6, ring atoms in each ring. Including, including a form in which a plurality of aryls are connected by single bonds. For example, naphthylene, biphenylene, terphenylene, anthrylene, indenylene, fluorenylene, pyrene, phenanthrylene, triphenylenylene, pyrenylene, perylenenylene, chrysenylene, naphthacenyl but is not limited to, rene and fluoranthenylene, and the like.

As used herein, the term "heteroarylene" is a divalent organic radical derived from an aromatic hydrocarbon by removing two hydrogens, and is selected from B, N, O, S. Si and P as a ring member (ring atom). It contains 1 to 4 heteroatoms, and the remaining ring members are carbon. Examples include, but are not limited to, furanylene, thiophenylene, pyridinylene, pyrimidinylene, pyrazinylene, pyridazinylene, triazinylene, and the like.

The term "cycloalkylene" used herein refers to a divalent organic radical having two bonding sites derived from a cyclic saturated hydrocarbon.

As used herein, the term "single bond" refers to the case where no atom exists at the corresponding site. For example, when Y is a single bond in the structure of X-Y-Z, X and Z are directly connected to form the structure of X-Z.

Hereinafter, the present invention will be specifically described.

One aspect of the present invention provides a photosensitive resin composition capable of preparing a cured film for a next-generation display device requiring a low-temperature curing process.

Specifically, the photosensitive resin composition according to one aspect may include a polymer including a repeating unit represented by Formula 1 below and a compound represented by Formula 2 below.

[Formula 1]

[Formula 2]

(In Chemical Formulas 1 and 2,

L ₁ is (C1-C20)alkylene, (C6-C20)arylene or (C3-C20)heteroarylene;

L ₂ and L ₃ are each independently a single bond, (C1-C20)alkylene, (C6-C20)arylene or (C3-C20)heteroarylene, and -CH ₂ - of the alkylene is -O- , -S-, -NH-, -C(=O)-, or a combination thereof;

X ₁ and X ₂ are each independently -O- or -NH-;

A is or It is one of four groups selected from;

L _a is a single bond, -O-, -C(=O)-, -S-, -SO ₂ -, (C1-C20)alkylene, (C6-C20)arylene, (C3-C20)heteroaryl may be rene or a combination thereof, and the alkylene may be further substituted with one or more selected from (C1-C10)alkyl and halo(C1-C10)alkyl;

R ₁ to R ₃ are each independently (C1-C10)alkyl or halo(C1-C10)alkyl;

p is an integer from 1 to 10;

a to c are each independently an integer of 0 to 2;

B is (C1-C20)alkylene, (C6-C20)arylene, (C3-C20)heteroarylene, (C3-C20)cycloalkylene, (C3-C20)heterocycloalkylene or ego;

Ar ₁ and Ar ₂ are each independently (C6-C20)arylene or (C3-C20)heteroarylene;

L _b is a single bond or (C1-C10)alkylene;

q is an integer from 1 to 10;

The alkylene, arylene, heteroarylene, cycloalkylene and heterocycloarylene of B and the arylene and heteroarylene of Ar ₁ and Ar ₂ are (C1-C10)alkyl, -NCO, -OCN, ( It may be further substituted with one or more selected from C6-C12) aryl and (C1-C10) alkoxy.)

The photosensitive resin composition according to one embodiment includes a combination of a polymer including a repeating unit represented by Chemical Formula 1 and a compound represented by Chemical Formula 2 (hereinafter, also referred to as an epoxy cyanate compound), so that a low-temperature process is required. A cured film applicable to a display device can be provided. Specifically, the photosensitive resin composition according to one embodiment can secure a sufficient degree of curing even in a low-temperature curing process, and can provide a cured film having excellent optical properties while realizing a reliable pattern.

Although not intending to be bound by a particular theory, for example, when the photosensitive resin composition includes only the polymer or only the epoxy cyanate compound, it may be difficult to achieve a sufficient degree of curing in a low-temperature curing process or to secure a high refractive index of 1.63 or more. there is.

Specifically, the repeating unit represented by Chemical Formula 1 may be represented by Chemical Formula 3 below.

[Formula 3]

(In Formula 3,

L ₁ is (C1-C20)alkylene or (C6-C20)arylene;

L ₁₁ to L ₁₄ are each independently (C1-C20)alkylene, (C6-C20)arylene or (C3-C20)heteroarylene;

X ₁ and X ₂ are each independently -O- or -NH-;

The definition of A is the same as that in Formula 1 above.)

For example, the X ₁ and X ₂ may be -O-, effectively preventing an increase in yellowness of the cured film after curing, and improving transmittance.

As the polymer has both an ester group and a carboxyl group in the repeating unit, sensitivity and developability may be further improved.

In addition, the polymer may have a terminal group including a hydroxyl group, and the terminal group including the hydroxyl group may be represented by Formula A below.

[Formula A]

(In the above formula A,

L ₄ is (C1-C10)alkylene;

L ₅ is a single bond or (C1-C10)alkylene.)

Specifically, L ₄ and L ₅ in Formula A may each independently represent (C1-C6)alkylene, more specifically, (C1-C3)alkylene.

The end groups may be capped at one or more ends of the polymer, for example, when the polymer has two ends, two end groups are capped, and when the polymer has a branched chain structure, at least three ends. Three or more terminal groups may be capped.

When the polymer according to one aspect has a terminal group including a hydroxyl group, a more precise pattern can be implemented.

For example, A may be a tetravalent group selected from the following structure.

(In the above structural formula,

L ₂₁ to L ₂₄ are each independently a single bond, -O-, -C(=O)-, -S-, -SO ₂ - or (C1-C7)alkylene, and the alkylene is (C1-C7 ) may be further substituted with one or more selected from alkyl and halo (C1-C7) alkyl;

R ₁ to R ₃ are each independently (C1-C7)alkyl or halo(C1-C7)alkyl;

a to c are each independently an integer of 0 to 2.)

Specifically, L ₂₁ and L ₂₂ are each independently a single bond, -O-, -C(=O)-, or -CR _a R _b -; L ₂₃ and L ₂₄ are each independently -O- or -S-; R _a and R _b may each independently be (C1-C3)alkyl or halo(C1-C3)alkyl.

A in Formula 1 may be, for example, a tetravalent group selected from the following structures.

Specifically, the repeating unit represented by Chemical Formula 1 may be represented by Chemical Formula 4 below.

[Formula 4]

(In Chemical Formula 4,

L ₁ is (C1-C7)alkylene or (C6-C12)arylene;

L ₁₁ to L ₁₄ are each independently (C1-C7)alkylene;

L ₃₁ is a single bond, -O-, -C(=O)- or -C(CF ₃ ) ₂ -;

p is an integer from 1 to 5.)

For example, L ₁ may be (C6-C12)arylene, specifically, phenylene, and more specifically, the repeating unit represented by Chemical Formula 1 may be represented by Chemical Formula 5 below.

[Formula 5]

(In Formula 5,

L ₃₁ is a single bond, -O-, -C(=O)- or -C(CF ₃ ) ₂ -.)

The repeating unit represented by Chemical Formula 1 may be, for example, selected from the following structures.

More specifically, the polymer may be selected from the following structures, but is not limited thereto.

(In the above structure,

n is an integer from 1 to 20.)

The weight average molecular weight of the polymer is 10000 g/mol or less, or 8000 g/mol or less, or 2000 g/mol to 8000 g/mol, or 3000 g/mol to 8000 g/mol, or 4000 g/mol to 8000 g /mol. As the polymer has the above weight average molecular weight, when used together with the epoxy cyanate compound, low-temperature curing can be more easily performed and a more precise pattern can be implemented.

In addition, in the epoxy cyanate compound, the B may be selected from the following structures, for example.

(In the above structure,

R ₁₁ to R ₁₆ are each independently (C1-C10)alkyl, -NCO, -OCN, (C6-C12)aryl, and (C1-C10)alkoxy;

d to i are each independently an integer of 0 to 4;

D ₁ to D ₃ are each independently a single bond or (C1-C10)alkylene;

m is an integer from 1 to 10.)

Specifically, the compound represented by Formula 2 may be represented by Formula 11 or Formula 12 below.

[Formula 11]

[Formula 12]

(In Chemical Formulas 11 and 12,

D ₁₁ to D ₁₃ are each independently a single bond or (C1-C5)alkylene;

R ₁₅ is (C1-C5)alkyl, -NCO or -OCN;

m is an integer from 1 to 10.)

More specifically, the compound represented by Formula 2 may be represented by Formula 13 or Formula 14 below.

[Formula 13]

[Formula 14]

(In Chemical Formulas 13 and 14,

R ₂₁ to R ₂₆ are each independently hydrogen or (C1-C3) alkyl.)

The compound represented by Chemical Formula 2 may be, for example, selected from the following structures, but is not limited thereto.

(In the above structure, m is an integer from 1 to 10.)

The photosensitive resin composition according to one aspect may include the epoxy cyanate compound and the polymer in a weight ratio of 1:1 to 1:10, specifically 1:1 to 1:8 weight ratio, more specifically 1:3 to It may be included in a 1:8 weight ratio. When the above weight ratio is satisfied, the degree of curing in a low-temperature curing process can be further improved, a more precise pattern can be implemented, and the optical properties of the cured film can be further improved.

The photosensitive resin composition according to an aspect may further include a photopolymerizable monomer, a photoinitiator, and a thermal curing agent.

For example, the photopolymerizable monomer may be a multifunctional monomer having an ethylenically unsaturated bond, and the multifunctional monomer includes one or more polymerizable functional groups selected from an acrylate group, a methacrylate group, and a vinyl group, or two or more polymerizable functional groups. It may contain from 8 to 8.

Non-limiting examples of the photopolymerizable monomer include 1,4-butanediol diacrylate, 1,3-butylene glycol diacrylate, 1,4-butanedioldi(meth)acrylate, and 1,3-butylene. Glycol dimethacrylate, 1,6-hexanediol di(meth)acrylate, ethylene glycol diacrylate, ethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate )Acrylate, polyethylene glycol di(meth)acrylate, dipentaerythritol hexaacrylate, pentaerythritol pentaacrylate, pentaerythritol tetraacrylate, pentaerythritol triacrylate, pentaerythritol diacrylate, dipentaerythritol pentaacrylate , dipentaerythritol triacrylate, dipentaerythritol diacrylate, sorbitol triacrylate, trimethylpropane triacrylate, pentaerythritol hexa(meth)acrylate, pentaerythritol penta(meth)acrylate, pentaerythritol tetra(meth) Acrylates, pentaerythritol tri(meth)acrylate, pentaerythritol di(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol tri(meth)acrylate, dipentaerythritol di(meth)acrylate , It may be one or two or more selected from sorbitol tri(meth)acrylate and trimethylpropane tri(meth)acrylate. More specifically, it may be pentaerythritol hexa(meth)acrylate, but is not limited thereto.

As the photosensitive resin composition according to one aspect further includes the photopolymerizable monomer as described above, the chemical resistance and curing degree of the cured film may be further improved.

The photoinitiator is not particularly limited as long as it is commonly used in the art, but examples thereof include acetophenone-based compounds, benzophenone-based compounds, triazine-based compounds, benzoin-based compounds, imidazole-based compounds, xanthone-based compounds, phosphide It may be one or two or more selected from pin-based compounds and oxime-based compounds. More specifically, the photoinitiator is 2,4-bistrichloromethyl-6-p-methoxystyryl-s-triazine, 2-p-methoxystyryl-4,6-bistrichloromethyl-s- Triazine, 2,4-trichloromethyl-6-triazine, 2,4-trichloromethyl-4-methylnaphthyl-6-triazine, 2-(o-chlorophenyl)-4,5-diphenyl Imidazole dimer, 2-(o-chlorophenyl)-4,5-di(m-methoxyphenyl) imidazole dimer, 2-(o-fluorophenyl)-4,5-diphenyl imidazole dimer , 2-(o-methoxyphenyl)-4,5-diphenyl imidazole dimer, 2-(o-methoxyphenyl)-4,5-diphenyl imidazole dimer, 2,4-di(p -methoxyphenyl)-5-phenyl imidazole dimer, 2-(2,4-dimethoxyphenyl)-4,5-diphenyl imidazole dimer, 2-(p-methylmercaptophenyl)-4, 5-diphenyl imidazole dimer, [1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazoyl-3-yl]-1-(O-acetyloxime), benzophenone, p- (Diethylamino)benzophenone, 2,2-dichloro-4-phenoxyacetophenone, 2,2-diethoxyacetophenone, 2-dodecylthioxanthone, 2,4-dimethylthioxanthone, 2,4- Diethylthioxanthone, 2,2-bis2-chlorophenyl-4,5,4,5-tetraphenyl-2-1,2-biimidazole, (E)-2-(acetoxyimino)-1 -(9,9-diethyl-9H-fluorene-2-yl)butanone, (E)-1-(9,9-dibutyl-7-nitro-9H-fluorene-2-yl)ethanone O-acetyl oxime, (Z)-2-(acetoxyimino)-1-(9,9-diethyl-9H-fluorene-2-yl)propanone, Irgacure 369, Irgacure 651, Irgacure 907 from Basf; At least one selected from the group consisting of Darocur TPO, Irgacure 819, OXE-01, OXE-02, OXE-03, OXE-04, Adecas N-1919, NCI-831 and NCI-930 may be used, but It is not limited.

The heat curing agent is not particularly limited as long as it is commonly used in the art, but may be, for example, one or two or more selected from imidazole-based compounds, dihydrazide-type compounds, and amine-based compounds, and curing time and storage In terms of stability, it may be an amine-based compound. More specifically, one or more selected from Evonik's Ancamine 2014AS, ADEKA's EH-5057PK, EH-4357S, and Hunstan's Jeffamine T-403 may be used, but is not limited thereto.

The photosensitive resin composition according to one aspect may further include a solvent. The solvent is an organic solvent, and in one embodiment, alcohols such as methanol and ethanol; ethers such as tetrahydrofuran, diethylene glycol dimethyl ether, and diethylene glycol diethyl ether; Propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, propellen glycol propyl ether acetate, propylene glycol butyl ether acetate acetate) and other alkylene glycol alkyl ether acetates; Aromatic hydrocarbons, such as toluene and xylene; ketones such as methyl ethyl ketone, cyclohexanone, and 4-hydroxy 4-methyl-2-pentanone; And methyl acetate, ethyl acetate, propyl acetate, butyl acetate, 2-hydroxyethylpropionate, 2-hydroxy-2-methylmethylpropionate, 2-hydroxy-2-methylethylpropionate, hydroxymethylacetate, hydroxyl Ethyl acetate, butyl hydroxyacetate, methyl lactate, ethyl lactate, propyl lactate, butyl lactate, methyl 3-hydroxypropionate, ethyl 3-hydroxypropionate, propyl 3-hydroxypropionate, butyl 3-hydroxypropionate, 2-hydroxy-3-methylmethylbutanoate, methoxymethylacetate, ethylmethoxyacetate, methoxypropylacetate, methoxybutylacetate, ethoxymethylmethylacetate, ethoxyethylacetate, ethoxypropylacetate, ethoxyacetic acid Butyl, methyl propoxyacetate, ethyl propoxyacetate, propyl propoxyacetate, butyl propoxyacetate, methyl butoxyacetate, ethyl butoxyacetate, propyl butoxyacetate, butyl butoxyacetate, methyl 2-methoxypropionate, 2 -Methoxyethylpropionate, 2-methoxypropylpropionate, 2-methoxybutylpropionate, 2-ethoxymethylpropionate, 2-ethoxyethylpropionate, 2-ethoxypropylpropionate, 2-ethoxybutylpropionate, 2-butoxymethylpropionate, 2-butoxyethylpropionate, 2-butoxypropylpropionate, 2-butoxybutylpropionate, 3-methoxymethylpropionate, 3-methoxyethylpropionate, 3-methoxypropylpropionate , 3-ethoxymethylpropionate, 3-ethoxyethylpropionate, 3-ethoxypropylpropionate, 3-ethoxybutylpropionate, 3-propoxymethylpropionate, 3-propoxyethylpropionate, 3-propoxypropylpropionate, esters such as butyl 3-propoxypropionate, methyl 3-butoxypropionate, ethyl 3-butoxypropionate, propyl 3-butoxypropionate, and butyl 3-butoxypropionate; It may be one or two or more selected from the like, but is not limited thereto.

The amount of the solvent is not limited in order to achieve a desired viscosity, but may be included in an amount of 30 to 90% by weight, more preferably 60 to 90% by weight, based on the total photosensitive resin composition.

The photosensitive resin composition according to one aspect may have a solid content of 10 to 80% by weight based on the total composition. The solid content is excluding the solvent, and may be included as 10 to 70% by weight, for example, 10 to 50% by weight, for example, 10 to 30% by weight based on the total photosensitive resin composition. Within the above-mentioned range of values, the effect desired in the present invention, that is, more remarkable in use, can be exhibited without impairing the stability of the composition.

The photosensitive resin composition according to one embodiment includes 50 to 90% by weight of the polymer, 1 to 30% by weight of the compound of Formula 2, 10 to 40% by weight of a photopolymerizable monomer, 1 to 10% by weight of a photoinitiator, and a heat curing agent based on solid content It may be included in 0.1 to 10% by weight. Preferably, 50 to 80% by weight of the polymer, 1 to 10% by weight of the compound of Formula 2, 10 to 30% by weight of a photopolymerizable monomer, 1 to 5% by weight of a photoinitiator, and 0.1 to 5% by weight of a thermal curing agent can

Specifically, the photosensitive resin composition may include a polymer and a photopolymerizable monomer in a weight ratio of 1:0.01 to 1:1, preferably 1:0.1 to 1:1, more preferably 1:0.2 to 1:0.8. It may be included in a weight ratio.

In addition, the photosensitive resin composition according to one aspect may further include a stabilizer, and in this case, the thermal stability and curing degree of the composition may be further improved.

The stabilizer may include at least one stabilizer selected from phenol-based stabilizers, hindered amine-based stabilizers, phosphorus-based stabilizers, boric acid ester-based stabilizers, and alkoxy amine radical-based stabilizers, and specifically, among phenol-based stabilizers and boric acid ester-based stabilizers It may include one or more selected stabilizers, but is not limited thereto.

Examples of the stabilizer include trimethyl borate, triethyl borate, tri-n-propyl borate, triisopropyl borate, tri-n-butyl borate, tripentyl borate, triallyl borate, trihexyl borate, tricyclohexyl borate, tri Octylborate, trinonylborate, tridecylborate, tridodecylborate, trihexadecylborate, trioctadecylborate, tris(2-ethylhexoxy)borane, bis(1,4,7,10)-tetraoxa undecyl)(1,4,7,10,13-pentaoxatetradecyl)(1,4,7-trioxaundecyl)borane, tribenzylborate, triphenylborate, tri-o-tolylborate, tri- m-tolyl borate, triethanolamine borate, tri-2-ethylhexyl borate, trimethylene borate, tris (trimethylsilyl) borate, tri-sec-butyl borate, tri-tert-butyl borate, methoxyethoxide boron, hydro quinone, catechol, resorcinol, p-methoxyphenol, t-butylcatechol, t-butyl hydroquinone, pyrogallol, p-benzoquinone, 2,5-di-t-butyl-p-benzoquinone, It may be picric acid, tri-p-nitrophenyl methyl, butylated hydroxytoluene, cyclohexanone oxime cresol, guayacol, o-isopropyl phenol, etc., specifically, trimethyl borate, triethyl borate, tri-n-propyl borate , triisopropyl borate, tri-n-butyl borate, tripentyl borate, triallyl borate, trihexyl borate, tricyclohexyl borate, trioctyl borate, but may be any one or more selected from, but is not limited thereto.

The amount of the stabilizer used is not particularly limited, and may be 0.1 to 5 parts by weight, specifically 0.1 to 1 part by weight, and specifically 0.1 to 0.5 parts by weight based on 100 parts by weight of the polymer.

Of course, the photosensitive resin composition according to one aspect may further include any additive commonly used in the art. In this case, the optional additive may be a silane coupling agent, a surfactant, a filler, a curing agent, a leveling agent, an adhesion assistant, an antioxidant, an ultraviolet absorber, an aggregation inhibitor, a chain transfer agent, a solvent, and the like.

In addition, one aspect of the present invention provides a cured film obtained by curing the photosensitive resin composition and an organic electronic device including the cured film.

Of course, any method for manufacturing a cured film according to an aspect and an organic electronic device including the cured film may be any known method within the range recognized by those skilled in the art.

Hereinafter, a method for forming a cured film using the photosensitive resin composition will be described in detail.

A cured film using the photosensitive resin composition according to one aspect may include forming a coating film by applying the photosensitive resin composition according to the present invention on a substrate and removing the solvent by prebaking; And photo-curing by irradiating light to the coating film.

For example, the coating may use a conventional coating method, and examples thereof include, but are not limited to, a spray method, a roll coater method, a spin coater method, a spin coater method, and the like.

For example, the prebaking may be performed under normal temperature conditions, and in one embodiment, it may be performed at a temperature of 50 to 200° C. for 1 to 5 minutes, but is not limited thereto.

For example, the light may be selected from visible light, ultraviolet light, deep ultraviolet light, electron beam, X-ray, etc., and a predetermined pattern may be formed using a pattern prepared in advance on the coating film. In one embodiment, the ultraviolet rays may use g-rays (wavelength: 436 nm), h-rays, i-rays (wavelength: 365 nm), etc., and the irradiation amount of these ultraviolet rays may be appropriately selected as needed. .

In addition, silicon, quartz, glass, silicon wafers, polymers, metals and metal oxides may be used as the substrate, but is not limited thereto. Specifically, the polymer substrate is triacetyl cellulose, acetyl cellulose butyrate, ethylene vinyl acetate copolymer, propionyl cellulose, butyryl cellulose, acetyl propionyl cellulose, polyester, polystyrene, polyamide, polyetherimide, poly Acrylic, polyimide, polyethersulfone, polysulfone, polyethylene, polypropylene, polymethylpentene, polyvinyl chloride, polyvinylidene chloride, polyvinyl alcohol, polyvinyl acetal, polyether ketone, polyether ether ketone, polyether sulfone Film substrates such as polymethyl methacrylate, polyethylene terephthalate, polybutylene terephthalate, polyethylene naphthalate, and polycarbonate may be used, but are not limited thereto.

A method for manufacturing a cured film according to an aspect may further include developing with a developing solution after the photocuring. This developing step is a process for removing the unexposed portion after photocuring through a mask for forming a target pattern, and may be performed by a conventional method such as a liquid addition method, a dipping method, a spray method, or the like.

In one embodiment, the developing step may be carried out in the form of removing the non-exposed portion by putting the substrate into a developing machine, spraying the substrate with a developing solution, and then cleaning it with DIW.

At this time, the developer is not limited as long as it is an alkaline aqueous solution, but non-limiting examples thereof include inorganic alkalis such as sodium hydroxide, potassium hydroxide, and sodium carbonate; primary amines such as n-propylamine; secondary amines such as diethylamine and n-propyldiamine; tertiary amines such as trimethylamine, methyldiethylamine, dimethylethylamine, and triethylamine; quaternary ammonium salts such as tetramethylammonium hydroxide and tetraethylammonium hydroxide; It may be an aqueous solution of one or more alkaline compounds selected from the like. In this case, the developing solution may be an aqueous solution containing 0.1 to 10% by weight of the above-described alkaline compound.

In addition, after the washing and drying step, a step of thermally curing at 200 ° C. or less, or 150 ° C. or less, or 100 ° C. or less, more specifically in the range of 50 to 100 ° C. using a heating device such as an oven may be further performed. .

The photosensitive resin composition according to one aspect can secure sufficient curing degree even under the low curing temperature conditions as described above, and can provide a cured film with excellent chemical resistance.

The cured film according to one aspect can be effectively used for electronic devices such as display devices, semiconductor devices, or optical waveguide materials, specifically, flattening films for thin film transistor (TFT) substrates such as liquid crystal display devices and organic EL display devices, It can be used as a protective film or insulating film for a touch panel sensor element, an interlayer insulating film for a semiconductor element, a flattening film for a solid-state imaging device, a micro lens array pattern, or a core or clad material for an optical waveguide such as an optical semiconductor element.

At this time, the thickness of the cured film may be appropriately changed according to the purpose, of course, but may be preferably formed to a thickness of 100 nm to 50 μm, specifically, to a thickness of 500 nm to 10 μm.

Hereinafter, the above-described implementation examples will be described in more detail through examples. However, the following examples are for illustrative purposes only and do not limit the scope of rights.

Physical properties were measured as follows.

(1) Weight average molecular weight and degree of dispersion

It was measured using Agilent Technologies' Waters Alliance 2695 Gel Permeation Chromatography (GPC). Shodex LF-804 was used as a column, Shodex polystyrene was used as a standard sample, and tetrahydrofuran was used as a solvent at a temperature of 40 °C and a flow rate of 1.0 mL/min.

(2) Development time

The organic film exposed using a mask was exposed to a developer for a specific time using an Apogee developer. Thereafter, the size of the unexposed area was measured using a microscope, and a point where the pattern size difference between the mask pattern size and the organic film pattern size was ±0.5 μm or less was set as the central development time.

(3) Taper angle

The taper angle means the inclination of the pattern edge, and the inside angle formed between the cured film and the inside of the pattern was measured using FE-SEM (S-4800, Hitachi).

(4) refractive index

The refractive index of the cured film on which no pattern was formed was measured using an ellipsometer (M-2000, J.A. Woollam).

(5) Chemical resistance

The cured film without a pattern was dipped in propylene glycol monomethyl ether acetate (PGMEA) at room temperature (25°C) for 5 minutes, then rinsed with ultrapure water before (thickness 1) and after (thickness) PGMEA treatment. The remaining film rate was calculated by measuring the film thickness of 2). Here, the higher the remaining film ratio, the better the chemical resistance.

[Production Example 1] Production of Polymer A-1

107 g of methylpyrrolidone (NMP), 2.35 g of triethylamine (TEA), and 2-hydroxyethyl acrylate (2- After stirring by adding 10.5 g of HEA), 11.6 g of 4,4'-thiobisbenzenethiol (TBT) was added and stirred at room temperature (25°C) for 2 hours. 21.4 g of tetrabutylammonium bromide (TBAB) and 4,4'-oxydiphthalic anhydride (ODPA) were added and stirred at 110°C for 4 hours. The reaction mixture was cooled and poured into water to form a precipitate, and the precipitate was filtered, thoroughly washed with water, and then dried under reduced pressure at 50° C. for 24 hours or more to prepare polymer A-1. The weight average molecular weight of Polymer A-1 determined by GPC method and standard polystyrene conversion was 6,300 g/mol, and the degree of dispersion was 1.71.

[Production Example 2] Production of Polymer A-2

In Preparation Example 1, except that 25 g of 3,3',4,4'-benzophenone tetracarboxylic dianhydride (BTDA) was used instead of 4,4'-oxydiphthalic anhydride (ODPA) prepared polymer A-2 in the same way. The weight average molecular weight of Polymer A-2 determined by GPC method and standard polystyrene conversion was 5,900 g/mol, and the degree of dispersion was 1.70.

[Production Example 3] Production of Polymer A-3

In Preparation Example 1, Polymer A- 3 was prepared. The weight average molecular weight of Polymer A-3 determined by GPC method and standard polystyrene conversion was 6,200 g/mol, and the degree of dispersion was 1.76.

[Preparation Example 4] Preparation of Compound B-1

Add 10 g of methyl ethyl ketone (MEK), 2.8 g of anhydrous potassium carbonate, and 4.6 g of bisphenol A to a three-necked flask equipped with a stirrer, temperature controller, and condenser, and then add 5 ml of distilled water and stir at 70 ° C for 30 minutes. did Thereafter, 1.9 g of epichlorohydrin was added dropwise to further react for 2 hours, and the reaction mixture was cooled while stirring until it reached room temperature. The resulting precipitate was filtered, put in a separatory funnel with dichloromethane/distilled water, shaken to separate the water layer, and the organic layer was washed with sodium hydroxide solution until neutralized. Finally, after separating the water layer, the mixture was dried under reduced pressure at 50° C. for 24 hours or longer to obtain compound a as a liquid product.

A three-necked flask equipped with a stirrer, a dropping panel, and a chiller was prepared, and 0.6 g of cyanogen bromide (BrCN), 7.5 g of the compound a, and 20 g of acetone were put into a reactor, and the temperature was lowered to 4° C. while stirring. After injecting 0.7 mL of triethylamine dropwise and stirring for 1 hour, the reaction mixture was cooled while stirring until it reached room temperature, and the resulting precipitate was filtered. Thereafter, the mixture was placed in a separatory funnel with 30 ml of benzene/30 ml of distilled water, shaken to separate the water layer, and then dried under reduced pressure at 50° C. for 24 hours or more to obtain compound B-1 as a liquid product.

[Production Examples 5 and 6]

Compounds B-2 and B-3 were prepared in the same manner as in Preparation Example 4, except that the compound of Table 1 was used instead of bisphenol A.

starting material product Production Example 4 Preparation Example 5 Preparation Example 6

[Example 1]

Preparation of photosensitive resin composition

17.5% by weight of Polymer A-1 of Preparation Example 1 as a high refractive index binder, 7% by weight of dipentaerythritol hexaacrylate (DPHA, Nippon Kayaku) as a photopolymerizable monomer, Compound B-1 of Preparation Example 4 as a thermosetting monomer 3% by weight, oxime-based photoinitiator (Irgacure OXE-04, BASF) 1% by weight, polyamine-based heat curing agent (Jeffamine T-403, Hunstan) 0.3% by weight, storage stabilizer pyrogallic acid 0.05% by weight, solvent The remaining amount of propylene glycol monomethyl ether acetate (sigma Aldrich) was mixed and dissolved at room temperature (25° C.), and filtered through a 0.45 μm filter to prepare the photosensitive resin composition of Example 1.

Manufacture of Cured Film

The photosensitive resin composition of Example 1 was coated on a glass substrate using a spin coater (TOP-8, Dong-A Trading Co., Ltd.), and then heated on a hot plate at 85° C. for 90 seconds to form a coating film having a thickness of 2.0 μm. The substrate coated with the coating film was exposed using a Canon exposure machine (MPA-600FA, Canon) using a mask engraved with patterns of various sizes. Thereafter, at room temperature (25 ° C.), developing with 2.38 wt% developer (tetraammonium hydroxide) for the time shown in Table 3 to dissolve and remove the unexposed area, wash with pure water for 60 seconds to form a pattern, Baked for 90 minutes in an 85° C. convection oven to prepare a patterned cured film. The physical properties are listed in Table 3 below.

In addition, the photosensitive resin composition of Example 1 was coated on a wafer substrate using a spin coater (TOP-8, Donga Trading Co., Ltd.), and then heated on a hot plate at 85° C. for 90 seconds to form a coating film. The entire surface of the substrate coated with the coating film was irradiated with light at an exposure amount of 50 mJ/cm ² using an exposure machine (MPA-600FA) manufactured by Canon Inc. without a mask. Thereafter, baking was performed in an 85° C. convection oven for 90 minutes to prepare a cured film having a thickness of 1.0 μm and no pattern formed thereon. The physical properties are listed in Table 3 below.

[Examples 2 to 6]

The photosensitive resin compositions and cured films of Examples 2 to 10 were prepared in the same manner as in Example 1, except that the components and contents were changed as shown in Table 2 below. The physical properties are listed in Table 3 below.

[Comparative Examples 1 to 5]

The photosensitive resin compositions and cured films of Comparative Examples 1 to 5 were prepared in the same manner as in Example 1, except that the components and contents were changed as shown in Table 2 below. The physical properties are listed in Table 3 below.

Content (% by weight) Example comparative example One 2 3 4 5 6 One 2 3 4 5 high refraction
polymer A-1 17.5 17.5 17.5 17.5 17.5 17.5 17.5 A-2 17.5 A-3 17.5 A-4 ^(a) 6.75 6.75 photopolymerizable monomer 7 7 7 7 7 7 7 7 7 7 7 thermosetting
monomer B-1 3.0 3.0 3.0 3.0 3 B-2 3.0 B-3 3.0 B-4 ^(b) 1.0 3.0 B-5 ^(c) 3.0 photoinitiator One One One One One One One One One One One heat curing agent 0.3 0.3 0.3 0.3 0.3 0.3 0.3 0.3 0.3 0.3 0.3 storage stabilizer 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.05 menstruum balance balance balance balance balance balance balance balance balance balance balance total 100 100 100 100 100 100 100 100 100 100 100 A-4 ^(a) : cardo type binder (KBR-101, KISCO)
B-4 ^(b) : Epoxy methacrylic (A50, KSM)
B-5 ^(c) : 1,4-bis (3-mercaptobutylyloxy) butane (BD1, SHOWADENKO)

exposure
(mJ/cm ² ) developing time
(sec) Taper angle
(°) refractive index chemical resistance thickness 1 thickness 2 △thickness Remaining film rate (%) Example 1 50 40 60.0 1.689 2.25 2.01 0.24 89.3% Example 2 50 30 58.1 1.685 2.19 2.01 0.18 88.2% Example 3 50 40 62.9 1.679 2.18 1.93 0.25 88.5% Example 4 50 40 58.3 1.682 2.05 1.79 0.26 87.5% Example 5 50 40 59.2 1.685 2.13 1.87 0.26 88.0% Example 6 50 30 63.2 1.689 2.21 2.02 0.19 91.4% Comparative Example 1 50 30 62.5 1.683 2.30 1.15 1.13 50.4% Comparative Example 2 50 80 80.2 1.580 2.50 1.75 0.69 71.7% Comparative Example 3 50 30 60.2 1.635 2.45 1.59 0.86 64.9% Comparative Example 4 50 30 65.0 1.635 2.48 2.10 0.38 84.7% Comparative Example 5 50 80 84.7 1.575 2.29 1.83 0.46 79.9%

As described in Table 3, it was confirmed that the cured films of Examples 1 to 6 showed high chemical resistance characteristics even under low temperature curing conditions of 85 °C. On the other hand, the cured films of Comparative Examples containing only the polymer or only the epoxy cyanate compound according to one aspect of the present invention had significantly reduced chemical resistance. That is, it can be seen that excellent chemical resistance under low-temperature curing conditions can be realized from the combination of the polymer and the epoxy cyanate compound according to one aspect of the present invention.

In addition, in Comparative Examples 3 and 4, a material containing epoxy or thiol, which is a functional group capable of curing at low temperatures, was used as a thermosetting monomer, and there was some improvement in low-temperature curing, but the effect was not significant compared to Examples. On the other hand, when used together with the epoxy cyanate compound (B-1) according to one aspect of the present invention as in Example 6, the degree of curing could be further increased.

Furthermore, it was confirmed that all of the cured films of Examples 1 to 6 could implement an excellent refractive index of 1.63 or more and implement a precise pattern with excellent sensitivity and developability.

That is, the photosensitive resin composition according to the present invention can realize a precise pattern, secure sufficient curing degree and chemical resistance even at a low temperature, provide a cured film having excellent optical properties, and have improved light extraction efficiency. A light emitting device may be provided.

Although the embodiments of the present invention have been described in more detail with reference to the accompanying drawings, the present invention is not necessarily limited to these embodiments, and may be variously modified and implemented without departing from the technical spirit of the present invention. . Therefore, the embodiments disclosed in the present invention are not intended to limit the technical idea of the present invention, but to explain, and the scope of the technical idea of the present invention is not limited by these embodiments. The protection scope of the present invention should be construed according to the claims below, and all technical ideas within the equivalent range should be construed as being included in the scope of the present invention.

Claims (18)

A photosensitive resin composition comprising a polymer containing a repeating unit represented by Formula 1 below and a compound represented by Formula 2 below:
[Formula 1]

[Formula 2]

In Formulas 1 and 2,
L ₁ is (C1-C20)alkylene, (C6-C20)arylene or (C3-C20)heteroarylene;
L ₂ and L ₃ are each independently a single bond, (C1-C20)alkylene, (C6-C20)arylene or (C3-C20)heteroarylene, and -CH ₂ - of the alkylene is -O- , -S-, -NH-, -C(=O)-, or a combination thereof;
X ₁ and X ₂ are each independently -O- or -NH-;
A is or It is one of four groups selected from;
L _a is a single bond, -O-, -C(=O)-, -S-, -SO ₂ -, (C1-C20)alkylene, (C6-C20)arylene, (C3-C20)heteroaryl may be rene or a combination thereof, and the alkylene may be further substituted with one or more selected from (C1-C10)alkyl and halo(C1-C10)alkyl;
R ₁ to R ₃ are each independently (C1-C10)alkyl or halo(C1-C10)alkyl;
p is an integer from 1 to 10;
a to c are each independently an integer of 0 to 2;
B is (C1-C20)alkylene, (C6-C20)arylene, (C3-C20)heteroarylene, (C3-C20)cycloalkylene, (C3-C20)heterocycloalkylene or ego;
Ar ₁ and Ar ₂ are each independently (C6-C20)arylene or (C3-C20)heteroarylene;
L _b is a single bond or (C1-C10)alkylene;
q is an integer from 1 to 10;
The alkylene, arylene, heteroarylene, cycloalkylene and heterocycloarylene of B and the arylene and heteroarylene of Ar ₁ and Ar ₂ are (C1-C10)alkyl, -NCO, -OCN, ( It may be further substituted with one or more selected from C6-C12) aryl and (C1-C10) alkoxy. According to claim 1,
A photosensitive resin composition in which the repeating unit represented by Formula 1 is represented by Formula 3 below:
[Formula 3]

In Formula 3,
L ₁ is (C1-C20)alkylene or (C6-C20)arylene;
L ₁₁ to L ₁₄ are each independently (C1-C20)alkylene, (C6-C20)arylene or (C3-C20)heteroarylene;
X ₁ and X ₂ are each independently -O- or -NH-;
The definition of A is the same as the definition in Formula 1 of claim 1. According to claim 2,
Wherein A is a tetravalent group selected from the following structures, the photosensitive resin composition:

In the above structural formula,
L ₂₁ to L ₂₄ are each independently a single bond, -O-, -C(=O)-, -S-, -SO ₂ - or (C1-C7)alkylene, and the alkylene is (C1-C7 ) may be further substituted with one or more selected from alkyl and halo (C1-C7) alkyl;
R ₁ to R ₃ are each independently (C1-C7)alkyl or halo(C1-C7)alkyl;
a to c are each independently an integer of 0 to 2; According to claim 3,
L ₂₁ and L ₂₂ are each independently a single bond, -O-, -C(=O)-, or -CR _a R _b -;
L ₂₃ and L ₂₄ are each independently -O- or -S-;
R _a and R _b are each independently (C1-C3) alkyl or halo (C1-C3) alkyl, the photosensitive resin composition. According to claim 1,
The photosensitive resin composition in which the repeating unit represented by Formula 1 is represented by Formula 4 below:
[Formula 4]

In Formula 4,
L ₁ is (C1-C7)alkylene or (C6-C12)arylene;
L ₁₁ to L ₁₄ are each independently (C1-C7)alkylene;
L ₃₁ is a single bond, -O-, -C(=O)- or -C(CF ₃ ) ₂ -;
p is an integer from 1 to 5; According to claim 1,
The repeating unit represented by the formula (1) is represented by the following formula (5), the photosensitive resin composition.
[Formula 5]

In Formula 5,
L ₃₁ is a single bond, -O-, -C(=O) - or -C(CF ₃ ) ₂ -. According to claim 1,
The repeating unit represented by Formula 1 is selected from the following structure, the photosensitive resin composition.

According to claim 1,
The weight average molecular weight of the polymer is 2,000 g / mol to 10,000 g / mol, the photosensitive resin composition. According to claim 1,
Wherein B is selected from the following structures, the photosensitive resin composition.

In the above structure,
R ₁₁ to R ₁₆ are each independently (C1-C10)alkyl, -NCO, -OCN, (C6-C12)aryl, and (C1-C10)alkoxy;
d to i are each independently an integer of 0 to 4;
D ₁ to D ₃ are each independently a single bond or (C1-C10)alkylene;
m is an integer from 1 to 10; According to claim 1,
The compound represented by Formula 2 is to be represented by Formula 11 or Formula 12, the photosensitive resin composition.
[Formula 11]

[Formula 12]

In Formulas 11 and 12,
D ₁₁ to D ₁₃ are each independently a single bond or (C1-C5)alkylene;
R ₁₅ is (C1-C5)alkyl, -NCO or -OCN;
m is an integer from 1 to 10; According to claim 1,
The compound represented by Formula 2 is selected from the following structure, the photosensitive resin composition.

In the above structure, m is an integer from 1 to 10. According to claim 1,
The compound represented by Formula 2 and the polymer are contained in a weight ratio of 1:1 to 1:10, the photosensitive resin composition. According to claim 1,
The photosensitive resin composition further comprises a photopolymerizable monomer, a photoinitiator and a thermal curing agent, the photosensitive resin composition. According to claim 13,
The photopolymerizable monomer is a polyfunctional monomer having an ethylenically unsaturated bond, the photosensitive resin composition. According to claim 13,
The photoinitiator is one or two or more selected from acetophenone-based compounds, benzophenone-based compounds, triazine-based compounds, benzoin-based compounds, imidazole-based compounds, xanthone-based compounds, phosphine-based compounds and oxime-based compounds, photosensitive resin composition. According to claim 13,
The heat curing agent is one or two or more selected from imidazole-based compounds, dihydrazide-type compounds and amine-based compounds, the photosensitive resin composition. A cured film obtained by curing the photosensitive resin composition according to any one of claims 1 to 16. An organic electronic device comprising the cured film of claim 17 .