KR102029733B1 - photosensitive resin composition - Google Patents

Abstract

The present invention relates to a photosensitive resin composition excellent in deep-hardening properties and, more specifically, to a photosensitive resin composition, which is advantageous for pattern formation and a development process using a photolithography method by mixing and using photopolymerization initiators with different absorption wavelength bands to exhibit excellent deep-hardening properties and can be suitably used as the photosensitive resin composition used in an organic light emitting material display panel.

Description

Photosensitive resin composition

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a photosensitive resin composition having excellent core curing properties. More particularly, organic photoluminescence is advantageous because it exhibits excellent core curing characteristics by mixing photopolymerization initiators having different absorption wavelength bands, and is advantageous for pattern formation and development processes using the photolithography method. The present invention relates to a photosensitive resin composition that can be suitably used as the photosensitive resin composition used in a raw material display panel.

In display devices, low temperature poly-silicon (LTPS) and oxide thin film transistors are being actively researched as devices for use in high resolution of UD (Ultra Definition) and high speed operation of 240 Hz or more.

In general, since the oxide thin film transistor changes the properties of the semiconductor by light, the above-described problem is minimized by introducing a light blocking layer. Since the formation of the light shielding layer is performed at a high temperature such as PE-CVD, a metal light shielding layer is mainly used as the light shielding layer. However, since the metal light shielding layer has high reflectivity, light is reflected between the source, the drain electrode and the light shielding layer, and parasitic voltage is generated between the source and the drain electrode to act as an element that resists the operation of the device. The problem is that the load on the line increases.

In particular, in the organic light emitting display and the transparent display, a light shielding layer may be introduced to eliminate the characteristic that the contrast ratio is significantly lowered by the reflection of the upper and lower metal wirings.

Common examples of the photopolymerization initiator used in the photosensitive composition include acetophenone derivatives, benzophenone derivatives, triazine derivatives, biimidazole derivatives, acylphosphine oxide derivatives and oxime ester derivatives. Absorbs and exhibits almost no color, has a high radical generating efficiency, and has excellent compatibility and stability with photosensitive composition materials. However, the earlier developed oxime derivative compounds have a low photoinitiation efficiency, in particular, a low sensitivity in the pattern exposure process, so the exposure should be increased, resulting in a decrease in production. In order to improve this disadvantage, various oxime ester derivative compounds have been proposed as photopolymerization initiators (eg, Korean Patent Laid-Open Nos. 10-2001-0082580 and 10-2007-0044753).

An object of the present invention is to use a photopolymerization initiator having a different absorption wavelength band, showing excellent deep curing properties, and advantageous to the pattern formation and development process using the photolithography method, which can be suitably used as a photosensitive resin composition for an organic light emitting display panel. It is providing a photosensitive resin composition.

In order to achieve the above object, the present invention provides a photosensitive resin comprising a photopolymerization initiator comprising [A] an alkali-soluble resin, [B] a polymerizable compound having an ethylenically unsaturated bond and [C] a compound of formulas 1 and 2 A composition is provided:

[Formula 1]

[Formula 2]

In Chemical Formula 1

R ₁ and R ₂ are each independently hydrogen, alkyl, aryl, alkoxy, arylalkyl, hydroxyalkyl, hydroxyalkoxyalkyl or cycloalkyl;

R ₃ is alkyl, aryl, arylalkyl or cycloalkyl.

According to another aspect of the present invention, a cured film formed from the photosensitive resin composition is provided.

According to another aspect of the present invention, a display device (eg, an organic light emitting display (OLED) device) including the cured film is provided.

Since the photosensitive resin composition of this invention shows the improved light-shielding property and shows the outstanding deep part hardening property, and is advantageous to the pattern formation and image development process using the photolithographic method, it can be used suitably as the photosensitive resin composition for organic light emitting display panels.

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

This invention relates to the photosensitive resin composition containing the photopolymerization initiator containing [A] alkali-soluble resin, [B] polymeric compound which has an ethylenically unsaturated bond, and [C] the compound of the said General formula (1) and (2).

[A] alkali-soluble resin

As the [A] alkali-soluble resin contained in the photosensitive resin composition of this invention, acrylic binder resin which is an acrylic polymer which has an acrylic unsaturated bond in an acrylic polymer or a side chain, silicone binder resin, cardo binder resin, and imide binder resin can be used. Can be.

Although not limited thereto, the alkali-soluble resin content included in 100 parts by weight of the photosensitive resin composition of the present invention is preferably 3 to 50 parts by weight, in terms of thin film properties such as pattern property control and heat resistance and chemical resistance. It is more preferable that it is 40 weight part. In addition, the alkali-soluble resin preferably has a weight average molecular weight of 2,000 to 300,000, and more preferably 3,000 to 100,000,00. Moreover, it is preferable that the dispersion degree of alkali-soluble resin is 1.0-10.0.

In one embodiment, the acrylic polymer may be a (co) polymer of monomers including an acrylic monomer. Examples of such acrylic monomers are methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, pentyl (meth) acrylate, hexyl (meth) acrylate, cyclohexyl (Meth) acrylate, heptyl (meth) acrylate, octyl (meth) acrylate, nonyl (meth) acrylate, decyl (meth) acrylate, lauryl (meth) acrylate, dodecyl (meth) acrylate, Tetradecyl (meth) acrylate, hexadecyl (meth) acrylate, isobonyl (meth) acrylate, adamantyl (meth) acrylate, dicyclopentanyl (meth) acrylate, dicyclopentenyl (meth) acrylic Rate, benzyl (meth) acrylate, 2-methoxyethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, (meth) acrylic acid, itaconic acid, maleic acid, maleic acid anhydride, maleic acid mono Alkyl ester Le, monoalkyl itaconate, monoalkyl fumarate, glycidyl (meth) acrylate, 3,4-epoxybutyl (meth) acrylate, 2,3-epoxycyclohexyl (meth) acrylate, 3,4 Epoxycyclohexylmethyl (meth) acrylate, 3-methyloxetane-3-methyl (meth) acrylate, 3-ethyloxetane-3-methyl (meth) acrylate, (meth) acrylamide, N -methyl (Meth) acrylamide etc. can be mentioned, These can be used individually or in combination of 2 or more types, respectively. Further, such acrylic monomers and monomers such as styrene, α-methylstyrene, acetoxystyrene, N -methylmaleimide, N -ethylmaleimide, N -propylmaleimide, N -butylmaleimide and N -cyclohexylmaleimide Copolymers obtained by copolymerizing are also usable in the present invention.

In one embodiment, the acrylic polymer having an acrylic unsaturated bond in the side chain may be a copolymer in which an epoxy resin is added to an acrylic copolymer containing carboxylic acid. For example, acrylic monomers containing carboxylic acids, such as acrylic acid, methacrylic acid, itaconic acid, maleic acid, and maleic acid monoalkyl esters, and alkyl (meth) such as methyl (meth) acrylate and hexyl (meth) acrylate. ) Acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, adamantyl (meth) acrylate, dicyclopentanyl (meth) acrylate, dicyclopentenyl (meth) acrylate, benzyl ( Meta) acrylate, 2-methoxyethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, styrene, α-methylstyrene, acetoxystyrene, N -methylmaleimide, N -ethylmaleimide, N - propyl maleimide, N - butyl maleimide, N - cyclohexyl maleimide, (meth) acrylamide, N - methyl (meth) obtained by copolymerizing acrylamide, etc., glycinate at one acrylic copolymer containing a carboxylic acid Cedylacrylate Epoxy, such as the nitrate, glycidyl methacrylate, 3, 4- epoxy butyl (meth) acrylate, 2, 3- epoxy cyclohexyl (meth) acrylate, and 3, 4- epoxy cyclohexyl methyl (meth) acrylate What was obtained by addition-reacting a monomer at the temperature of 40-180 degreeC can be used as binder resin.

Another example of the acrylic polymer having an acrylic unsaturated bond in the side chain is a copolymer obtained by adding a carboxylic acid to an acrylic copolymer containing an epoxy group. For example, glycidyl acrylate, glycidyl methacrylate, 3,4-epoxybutyl (meth) acrylate, 2,3-epoxycyclohexyl (meth) acrylate, 3,4-epoxycyclohexylmethyl Acrylic monomer containing epoxy groups, such as (meth) acrylate, Alkyl (meth) acrylates, such as methyl (meth) acrylate and hexyl (meth) acrylate, cyclohexyl (meth) acrylate, and isobornyl (meth) acryl Rate, adamantyl (meth) acrylate, dicyclopentanyl (meth) acrylate, dicyclopentenyl (meth) acrylate, benzyl (meth) acrylate, 2-methoxyethyl (meth) acrylate, 2- Ethoxyethyl (meth) acrylate, styrene, α-methylstyrene, acetoxystyrene, N -methylmaleimide, N -ethylmaleimide, N -propylmaleimide, N -butylmaleimide, N -cyclohexylmaleimide , (Meth) acrylamide, N -methyl (meta 40 to 180 acrylic monomers containing carboxylic acids such as acrylic acid, methacrylic acid, itaconic acid, maleic acid and maleic acid monoalkyl esters in an acrylic copolymer containing an epoxy group obtained by copolymerizing monomers such as acrylamide. What was obtained by addition reaction at the temperature of ° C can be used as the binder resin.

In one embodiment, the cardo-based binder resin contains a polymer unit derived from a compound represented by the following formula (3).

[Formula 3]

In Chemical Formula 3,

이고;Each R ₄ is independently hydrogen or

ego;

R ₅ and R ₆ are the same as or different from each other, and are each independently hydrogen, hydroxy, a straight, branched or cyclic alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 10 carbon atoms; R ₇ is hydrogen, a straight, branched or cyclic alkyl group of 1 to 20 carbon atoms, an aryl group of 6 to 10 carbon atoms, an unsaturated hydrocarbon group of 2 to 10 carbon atoms, or —C (═O) —R _{7 ′} wherein R _{7 '} is hydrogen, hydroxy, a straight, branched or cyclic alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 10 carbon atoms;

이고, Y is

ego,

Wherein R ₈ , R ₉ and R ₁₀ are the same as or different from each other, and are each independently hydrogen, a straight chain having 1 to 20 carbon atoms, a linear, branched or cyclic alkyl group substituted with halogen, or an aryl group having 6 to 10 carbon atoms. .

In one embodiment, the imide-based binder resin contains a polymerized unit derived from a compound represented by the following formula (4).

[Formula 4]

In Chemical Formula 4,

Each R ₁₁ is independently hydrogen, hydroxy, a straight, branched or cyclic alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 10 carbon atoms;

이며, 여기서 R₁₃은 수소, 하이드록시, 탄소수 1 내지 20의 직쇄상, 분지상 또는 환상의 알킬기, 탄소수 2 내지 20의 직쇄상, 분지상 또는 환상의 알케닐기 또는 탄소수 6 내지 10의 아릴기이다.R ₁₂ is hydrogen, a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 10 carbon atoms, an unsaturated hydrocarbon group having 2 to 10 carbon atoms, or

Wherein R ₁₃ is hydrogen, hydroxy, a straight, branched or cyclic alkyl group having 1 to 20 carbon atoms, a straight, branched or cyclic alkenyl group having 2 to 20 carbon atoms or an aryl group having 6 to 10 carbon atoms .

In one embodiment, the silicone binder resin contains a polymer unit represented by the following formula (5).

[Formula 5]

XR ₁₄ SiO _{(4-n) / 2}

In Chemical Formula 5,

R ₁₄ is a linear or branched alkylene group having 1 to 20 carbon atoms, an arylene group having 6 to 20 carbon atoms, an aryl-alkylene group having 7 to 20 carbon atoms in total, an alkyl-arylene group having 7 to 20 carbon atoms in total, or a total carbon number An alkylene-arylene group of 7 to 20; X is a hydroxy, carboxylic acid group, carboxylic anhydride group, carboxylic anhydride derivative group, imide group, imide derivative group, amide group, amide derivative group, amine group or mercanto; n is an integer from 0 to 3; The polymer unit in which n = 3 may be used together with another polymer unit in which n is not 3.

Further, for example, tetraalkoxy silane, trialkoxy silane, methyl trialkoxy silane, ethyl trialkoxy silane, n-propyl trialkoxy silane, isopropyl trialkoxy silane, n-butyl trialkoxy silane, tert-butyl trialkoxy silane , Phenyl trialkoxy silane, naphtha trialkoxy silane, vinyl trialkoxy silane, methacryloxymethyl trialkoxy silane, 2-methacryloxyethyl trialkoxy silane, 3-methacryloxypropyl trialkoxy silane, 3-methacryloxypropyl Methyl dialkoxy silane, 3-methacryloxypropyl ethyl dialkoxy silane, acryloxymethyl trialkoxy silane, 2-acryloxyethyl trialkoxy silane, 3-acryloxypropyl trialkoxy silane, 3-acryloxypropyl methyl dialkoxy silane , 3-acryloxypropyl ethyl dialkoxy silane, 3-glycidyloxypropyl trialkoxy silane, 2-epoxycyclohexylethyl Group consisting of trialkoxy silane, 3-epoxycyclohexylpropyl trialkoxy silane, dimethyl alkoxy silane, diethyl dialkoxy silane, dipropyl dialkoxy silane, diphenyl dialkoxy silane, diphenyl silanediol and phenylmethyl dialkoxysilane One or two or more monomers selected from can be used. Here, alkoxy may be linear, branched or cyclic aliphatic or aromatic alkoxy having 1 to 7 carbon atoms. In addition, a hydrolyzable halogenated silicone compound may be used as the monomer.

[B] a polymerizable compound having an ethylenically unsaturated bond

The polymerizable compound having the [B] ethylenically unsaturated bond in the photosensitive resin composition of the present invention crosslinks by photoreaction when forming a pattern to form a pattern, and crosslinks at high temperature to impart chemical resistance and heat resistance. do.

Although not limited thereto, the polymerizable compound content having the ethylenically unsaturated bond contained in 100 parts by weight of the photosensitive resin composition of the present invention may be, for example, 0.001 to 40 parts by weight, and more specifically 0.01 to 30 parts by weight. It may be wealth. When too much polymerizable compound having an ethylenically unsaturated bond is added to the photosensitive resin composition, a crosslinking degree may be too high, which may cause a disadvantage in that the ductility of the pattern is lowered.

In one embodiment, the polymerizable compound having an ethylenically unsaturated bond may be a polymerizable unsaturated compound having a hydroxyl group or a carboxyl group.

In one embodiment, the polymerizable compound having an ethylenically unsaturated bond may be methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, lauryl Alkyl ester of (meth) acrylic acid, such as (meth) acrylate, glycidyl (meth) acrylate, polyethyleneglycol mono (meth) acrylate whose number of ethylene oxide groups is 2-14, ethylene glycol di (meth) acrylate , Polyethylene glycol di (meth) acrylate having 2 to 14 ethylene oxide groups, polypropylene glycol di (meth) acrylate having 2 to 14 propylene oxide groups, trimethylolpropanedi (meth) acrylate, bisphenol A Diglycidyl ether acrylic acid adduct, phthalic acid diester of dihydroxy ethyl (meth) acrylate, toluene di of dihydroxyethyl (meth) acrylate Socyanate adduct, trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) Acrylic acid of a polyhydric glycidyl compound, such as a compound obtained by esterifying a polyhydric alcohol with α, β-diunsaturated carboxylic acid, such as acrylate and dipentaerythritol tri (meth) acrylate, and an adduct of trimethylolpropanetriglycidyl ether acrylic acid And an adduct. These may be used alone or in combination of two or more thereof.

[C] Photopolymerization Initiator

[C] photoinitiator contained in the photosensitive resin composition of the present invention by using a mixture of two or more kinds of compounds having different absorption wavelengths, that is, a compound represented by the following formulas (1) and (2) to increase the core curing properties and excellent pattern formation To give.

[Formula 1]

[Formula 2]

In Chemical Formula 1

R ₁ and R ₂ are each independently hydrogen, alkyl, aryl, alkoxy, arylalkyl, hydroxyalkyl, hydroxyalkoxyalkyl or cycloalkyl;

R ₃ is alkyl, aryl, arylalkyl or cycloalkyl.

In the above, specifically, the alkyl and alkoxy may have 1 to 30 carbon atoms, the cycloalkyl may have 3 to 30 carbon atoms, and the aryl may have 6 to 30 carbon atoms. More specifically, the alkyl and alkoxy may have 1 to 20 carbon atoms, the cycloalkyl may have 3 to 20 carbon atoms, and the aryl may have 6 to 20 carbon atoms.

More specifically, R ₁ and R ₂ are each independently hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n- Hexyl, i-hexyl, n-octyl, n-decyl, i-decyl, n-dodecyl, cyclopentyl, cyclohexyl, phenyl, benzyl, naphthyl, biphenyl, terphenyl, anthryl, indenyl, phenanthryl , Methoxy, ethoxy, n-propyloxy, i-propyloxy, n-butoxy, i-butoxy, t-butoxy, hydroxymethyl, hydroxyethyl, hydroxy n-propyl, hydroxy n- Butyl, hydroxy i-butyl, hydroxy n-pentyl, hydroxy i-pentyl, hydroxy n-hexyl, hydroxy i-hexyl, hydroxymethoxymethyl, hydroxymethoxyethyl, hydroxymethoxypropyl, Hydroxymethoxybutyl, hydroxyethoxymethyl, hydroxyethoxyethyl, hydroxyethoxypropyl, hydroxyethoxybutyl, hydroxyethoxypentyl or hydroxyethoxyhexyl;

R ₃ is methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, i-hexyl, cyclopentyl, cyclohexyl, or Phenyl.

Compounds of Formula 1 according to the present invention may include one or more representatively selected from the following groups, but the following compounds do not limit the present invention:

There is no particular limitation on the content ratio between the compounds of Formulas 1 and 2 included in the photopolymerization initiator of the present invention. Preferably the compounds of Formula 1 and Formula 2 are in a weight ratio of 1: 0.1 to 1:10, preferably 1: 0.3 to 1: 8, more preferably 1: 0.5 to 1: 5, still more preferably 1: 0.7 to 1: 2, even more preferably 1: 0.75 to 1: 1.9 can be used by mixing.

Although not limited to this, from the aspect for smoothing the core hardening, the photopolymerization initiator content contained in 100 parts by weight of the photosensitive resin composition of the present invention is effective to 0.01 to 10 parts by weight, 0.1 to 5 parts by weight Denial is more effective.

The photosensitive resin composition of this invention may further contain the silicone type compound which has an epoxy group or an amine group as an adhesion | attachment adjuvant as needed other than the said [A]-[C] component.

The silicone compound may be used to improve adhesion between the ITO electrode and the photosensitive resin composition and to increase heat resistance after curing, and the amount thereof may be 0.0001 to 3 parts by weight based on 100 parts by weight of the composition, but is not limited thereto. no.

In one embodiment, the silicon-based compound having an epoxy group or an amine group is (3-glycidoxypropyl) trimethoxysilane, (3-glycidoxypropyl) triethoxysilane, (3-glycidoxyoxypropyl) ) Methyldimethoxysilane, (3-glycidoxyoxy)) methyldiethoxysilane, (3-glycidoxyoxy) dimethylmethoxysilane, (3-glycidoxypropyl) dimethylethoxysilane, 3 , 4-epoxybutyltrimethoxysilane, 3,4-epoxybutyltriethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 2- (3,4-epoxycyclo Hexyl) ethyl triethoxy silane, aminopropyl trimethoxy silane, etc. are mentioned, These can be used individually or in mixture of 2 or more types, respectively.

In addition, the photosensitive resin composition of the present invention may further include one or more compatible additives such as a photosensitizer, a thermal polymerization inhibitor, an antifoaming agent, a leveling agent, a dispersing agent, and the like as necessary.

Moreover, the photosensitive resin composition of this invention is 1 type chosen from the group which consists of a thioxanthone type compound, a ketone type compound, a biimidazole type compound, a triazine type compound, O-acyl oxime type compound, and a thiol type compound as needed. Or two or more compounds.

The photosensitive resin composition of this invention contains a solvent. Ethyl acetate, butyl acetate, diethylene glycol dimethyl ether, diethylene glycol dimethyl ethyl ether, methyl methoxy propionate, ethyl ethoxy propionate (EEP) in consideration of binder compatibility with the components of the composition , Ethyl lactate, propylene glycol monomethyl ether acetate (PGMEA), propylene glycol methyl ether propionate (PGMEP), propylene glycol methyl ether, propylene glycol propyl ether, methyl cellosolve acetate, ethyl cellosolve acetate, diethylene Glycol methyl acetate, diethylene glycol ethyl acetate, acetone, methyl isobutyl ketone, cyclohexanone, dimethylformamide (DMF), N , N -dimethylacetamide (DMAc), N -methyl-2-pyrrolidone (NMP ), γ-butyrolactone, diethyl ether, ethylene glycol dimethyl ether, diglyme, tetrahydrofuran (THF), methanol, ethane , Propanol, iso-propanol, methyl cellosolve, ethyl cellosolve, diethylene glycol methyl ether, diethylene glycol ethyl ether, dipropylene glycol methyl ether, toluene, xylene, hexane, heptane, octane, or the like, each alone or It can mix and use 2 or more types.

The solvent may be added 10 to 95 parts by weight based on 100 parts by weight of the total composition, it is preferable to adjust the viscosity of the composition is in the range of 1 to 50 cps.

Hereinafter, the representative compounds of the present invention will be described in detail with reference to Examples and Comparative Examples for a detailed understanding of the present invention. However, embodiments according to the present invention can be modified in many different forms, the scope of the present invention should not be construed as limited to the embodiments described below. Embodiments of the present invention are provided to more fully describe the present invention to those skilled in the art.

[ Example ]

Synthesis Example [A] Preparation of Alkali Soluble Resin

a) A-1 resin preparation

Methacrylic acid, methylmethacrylate and glycidyl methacrylate and dicyclopentanyl acrylate were each added in a molar ratio of 10: 30: 40: 20, and then 30 parts by weight of these mixtures, 1 weight of V-65 with a thermal initiator. Part and 70 parts by weight of methyl 3-methoxy propionate were placed in a reaction vessel, and then polymerized with stirring for 8 hours while maintaining the temperature at 65 ° C in a nitrogen atmosphere. The weight average molecular weight of the copolymer thus prepared was Mw = 25,000.

b) A-2 resin preparation

231 g of 9,9-bis (4-glycidyloxyphenyl) fluorene, 150 mg of tetrabutylammonium chloride and 74 g of propionic acid were heated at 120 ° C. for 12 hours. Propionic acid was analyzed by GC to terminate the reaction, yielding a solid phase intermediate (yield: 92%). 280 g of the obtained solid phase intermediate was dissolved in 400 mL of propylene glycol methyl ether acetate (PGMEA), and then 101.4 g of 3,3 ', 4,4'-bipetyltetracarboxylic acid anhydride, tetra 500 mg of butylammonium chloride were added and reacted at 120 degreeC. Finally, 35 g of phthalic anhydride was mixed and terminated after the reaction at 90 ° C. to obtain A-2 resin, which is a cardo polymer. The weight average molecular weight was 3,800.

c) A-3 resin preparation

231 g of 9,9-bis (4-glycidyloxyphenyl) fluorene, 150 mg of tetrabutylammonium chloride, 100 mg of 2,6-di-t-butyl-4-methylphenol and 72 g of acrylic acid were heated at 120 ° C. for 12 hours. Reaction. Acrylic acid was analyzed by GC to terminate the reaction, yielding a solid phase intermediate (yield: 92%). After dissolving 280 g of the obtained solid-phase intermediate in 400 mL of PGMEA, 101.4 g of 3,3 ', 4,4'-bifetyltetracarboxylic acid anhydride and 500 mg of tetrabutylammonium chloride were added and reacted at 120 占 폚. Finally, 35 g of phthalic anhydride was mixed and terminated after the reaction at 90 ° C. to obtain A-3 resin, which is a cardo polymer. The weight average molecular weight was 4,800.

Example  1 to 15 and Comparative example  1 to 12: Preparation of Photosensitive Resin Composition

40 parts by weight of the [A] alkali-soluble resin prepared in Synthesis Example 1 as the binder polymer, [B] 18 parts by weight of ADPH (shin-nakamura) which is a photopolymerizable polyfunctional monomer as the polymerizable compound having an ethylenically unsaturated bond, [ C] 0.3 to 0.42 parts by weight of the photopolymerization initiator and the remaining amount of the organic solvent methyl 3-methoxy propionate (MMP) were added and mixed for 3 hours using a shaker. This mixed photosensitive solution was filtered using a 0.5 micron filter to prepare a photosensitive composition. The types and amounts of alkali-soluble resins and photopolymerization initiators used in the above Examples and Comparative Examples are shown in Table 1 below.

[Compound 1]

[Compound 2]

[Compound 3] (IRGACURE® 184)

[Compound 4] (IRGACURE® 819)

TABLE 1

<Property evaluation>

Spin-coating the photosensitive resin composition prepared in Examples 1 to 15 and Comparative Examples 1 to 12 on glass to pre-bake at about 100 ° C. for 2 minutes to form a uniform film having a thickness of about 3.0 μm. It was. After exposing the film using a circular isolated pattern photomask having a diameter of 5 to 25 μm, the pattern was developed for 60 seconds with an aqueous KOH alkali solution having a pH of 11.3 to 11.7 and washed with deionized water. After post-bake at 230 ° C. for about 20 minutes, the state of the pattern was observed under a microscope to observe the degree of micropattern remaining. After measuring the bottom size with a 3D profiler, SEM (Scanning electron) was finally obtained. The presence or absence of an under cut was confirmed with a microscope equipment, and the evaluation results are shown in Table 2 below.

1) Formable fine pattern level

The micro pattern level that can be formed was confirmed by the optical microscope after the photolithography process the mask size level of the pattern is formed.

2) Bottom Size

The actual size of the pattern formed in the same mask was measured with a 3D surface profiler.

3) Check for under cut

The pattern profile image measured by the SEM (Scanning electron microscope) equipment was checked to determine the presence or absence of an undercut.

TABLE 2

Claims (9)

[A] an alkali-soluble resin, [B] a polymerizable compound having an ethylenically unsaturated bond, and [C] a photopolymerization initiator comprising a compound of the following formulas (1) and (2),
The weight ratio of the compound of formula 1 to the compound of formula 2 is 1: 0.1 to 1:10,
Photosensitive resin composition:
[Formula 1]

[Formula 2]

In Chemical Formula 1
R ₁ and R ₂ are each independently hydrogen, alkyl, aryl, alkoxy, arylalkyl, hydroxyalkyl, hydroxyalkoxyalkyl or cycloalkyl;
R ₃ is alkyl, aryl, arylalkyl or cycloalkyl. The method of claim 1,
R ₁ and R ₂ are each independently hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, i- Hexyl, n-octyl, n-decyl, i-decyl, n-dodecyl, cyclopentyl, cyclohexyl, phenyl, benzyl, naphthyl, biphenyl, terphenyl, anthryl, indenyl, phenanthryl, methoxy, Ethoxy, n-propyloxy, i-propyloxy, n-butoxy, i-butoxy, t-butoxy, hydroxymethyl, hydroxyethyl, hydroxy n-propyl, hydroxy n-butyl, hydroxy i-butyl, hydroxy n-pentyl, hydroxy i-pentyl, hydroxy n-hexyl, hydroxy i-hexyl, hydroxymethoxymethyl, hydroxymethoxyethyl, hydroxymethoxypropyl, hydroxymethoxy Butyl, hydroxyethoxymethyl, hydroxyethoxyethyl, hydroxyethoxypropyl, hydroxyethoxybutyl, hydroxyethoxypentyl or hydroxyethoxyhexyl;
R ₃ is methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, i-hexyl, cyclopentyl, cyclohexyl, or Phenyl,
Photosensitive resin composition. The method of claim 1,
A photosensitive resin composition, wherein the compound of Formula 1 is at least one selected from the following group:

delete The photosensitive resin composition of Claim 1 whose (A) alkali-soluble resin is 1 or more types chosen from acrylic resin, silicone resin, cardo resin, and imide resin. The photosensitive resin composition of Claim 1 whose polymerizable compound which has [B] ethylenically unsaturated bond is a polymerizable unsaturated compound which has a hydroxyl group or a carboxyl group. The photosensitive resin composition of Claim 1 whose [C] photoinitiator is 0.01-10 weight part with respect to 100 weight part of photosensitive resin compositions. The cured film formed from the photosensitive resin composition of any one of Claims 1-3 and 5-7. A display element comprising the cured film of claim 8.