KR101251684B1 - Composition for alkali developable resin, alkali developable resin made therefrom, method for producing the same and photosensitive resin composition comprising the same - Google Patents

Abstract

The present invention provides a composition for producing an alkali-soluble resin comprising a) a diacid compound having two polymerizable unsaturated groups, b) an epoxy resin and c) a solvent, an alkali-soluble resin prepared from the composition for preparing an alkali-soluble resin, It provides a photosensitive resin composition comprising the preparation method and the alkali-soluble resin. Alkali-soluble resin according to the present invention is excellent in storage stability, easy to store, can be stored for a long time, the photosensitive resin composition comprising the alkali-soluble resin is excellent in sensitivity and excellent in chemical resistance and development margin.

Alkali-soluble resin, chemical resistance, development margin

Description

Composition for preparing alkali-soluble resin, alkali-soluble resin prepared therefrom, a method for preparing the same, and a photosensitive resin composition comprising the same.

The present invention relates to a composition for producing an alkali-soluble resin, an alkali-soluble resin prepared therefrom, a method for preparing the same, and a photosensitive resin composition comprising the alkali-soluble resin.

The photopolymerizable negative photosensitive resin composition is used in various applications, such as a photosensitive agent for manufacturing color filters, an overcoat photosensitive agent, a column spacer, an insulating material having light shielding properties, and is typically an alkali-soluble resin, a polymerizable compound having an ethylenically unsaturated bond, and a photopolymerization. Initiator and solvent.

Such a photosensitive resin composition forms a coating film by apply | coating the photosensitive resin composition on a board | substrate, after exposing by a radiation irradiation to a specific part of this coating film using a photomask etc., it develops a non-exposed part and forms a pattern. Can be used in such a way.

Recently, as the use of liquid crystal displays (LCDs) has been expanded from conventional notebook monitors to desktop monitors, LCD TVs, and the like, pigment concentrations in color filter photosensitizers are increased to realize high quality colors, and pigments are finely dispersed.

In addition, the resin black matrix has a higher concentration of light blocking materials such as carbon black or titanium black in the resin black matrix composition to realize a thinner film.

As the concentration of pigment or light-shielding material contained in the photosensitive resin composition increases, the amount of irradiation energy that can be delivered to the lower portion of the patterned film decreases rapidly. Thus, alkali-soluble resin that can only serve as a binder improves production yield. In order to meet the requirements of LCD panel makers, which are reducing their exposure, they have reached their limit.

As an alternative to this, a technique for densifying the coating film of a resin produced by introducing an unsaturated double bond group into the side chain of an alkali-soluble binder resin, such as Japanese Patent Laid-Open Publication No. 2003-241374 and Japanese Patent Laid-Open Publication No. 2004-219979, etc. Known as

However, the alkali-soluble resin provided in this document has a limit that can increase the fraction of unsaturated double bond groups that can be introduced into the side chain in the manufacturing process, in particular, the level of high sensitivity in the resin black matrix is not satisfactory.

On the other hand, Japanese Patent Publication No. 1997-325494, Japanese Patent Publication No. 2001-354735, Japanese Patent Application Laid-Open No. 2005-77451, and Korean Patent in order to sufficiently introduce unsaturated double bonds that can participate in optical crosslinking in the binder resin. JP-A-2005-0021902 and the like provide a carboxyl group-containing cardo-based binder resin obtained by reacting a diol compound having one or more polymerizable unsaturated groups in an molecule with an acid dianhydride. However, the copolymer prepared in this way can achieve high sensitivity, but there is a problem in that the storage stability at room temperature is poor because the molecular weight is severely changed by the unreacted anhydride group remaining in a small amount in the manufacturing process.

In general, cardo-based binder resin is highly sensitive and excellent in heat resistance and chemical resistance without being affected by oxygen. However, due to the bulky molecular structure, the adhesion tends to be inferior. Furthermore, in the case of the black matrix, since the content of the carbon black pigment is higher than that of other colored photosensitive resin compositions in order to match the optical density, there is a problem in that the deterioration of adhesion is more severe.

The present inventors found that a diacid compound having two polymerizable unsaturated groups in a molecule and an alkali-soluble resin formed from an epoxy resin have excellent storage stability, and the photosensitive resin composition containing the alkali-soluble resin has sensitivity, adhesion, and resistance. It was found that the chemical properties and development margin were excellent. Accordingly, the present invention provides a composition for preparing an alkali-soluble resin comprising a diacid compound having two polymerizable unsaturated groups and an epoxy resin, an alkali-soluble resin prepared therefrom, a method for preparing the same, and a photosensitive resin composition including the alkali-soluble resin. It aims to do it.

The alkali-soluble resin according to the present invention not only has excellent storage stability, but also the photosensitive composition containing the same has excellent sensitivity, chemical resistance, and development margin as compared with the existing photosensitive composition.

As one embodiment of the present invention for achieving the above object, there is provided a composition for producing an alkali-soluble resin comprising a) a diacid compound having two polymerizable unsaturated groups, b) an epoxy resin and c) a solvent.

As another embodiment of the present invention, (i) mixing a) a diacid compound having two polymerizable unsaturated groups and b) an epoxy resin in a 1: 0.3 to 1.1 molar ratio in a solvent; And (ii) heating the mixture at 80 to 130 ° C. for 4 to 24 hours.

As another embodiment of the present invention, an alkali-soluble resin prepared from the composition for producing an alkali-soluble resin is provided.

As another embodiment of the present invention, there is provided a photosensitive resin composition comprising the alkali-soluble resin, a polymerizable compound having an ethylenically unsaturated bond, a photopolymerization initiator, and a solvent.

As another embodiment of this invention, the hardened | cured material formed from the said photosensitive resin composition is provided.

Hereinafter, the present invention will be described in detail.

As one embodiment of the present invention, there is provided a composition for producing an alkali-soluble resin comprising a) a diacid compound having two polymerizable unsaturated groups, b) an epoxy resin and c) a solvent.

The a) diacid compound having two polymerizable unsaturated groups is a compound providing a photocrosslinkable ethylenically unsaturated group and b) a diacid group capable of alternating copolymerization with an epoxy resin. The a) diacid compound having two polymerizable unsaturated groups is a compound represented by the following Chemical Formula 1 which is presented through a secondary reaction of an acid anhydride through a condensation reaction between a diglycidyl ether compound and (meth) acrylic acid. Here, (meth) acrylic acid means acrylic acid or methacrylic acid.

In Formula 1,

R is hydrogen or methyl,

(단, Z는 직접 결합 또는 C₁~C₆의 알킬렌, 케톤, -O-, -S-, -SO₂-, 헥사플루오로프로필렌, -OC₆H₄O-, -OC₆H₄C(CH₃)₂C₆H₄O-로 이루어지는 군으로부터 선택되는 어느 하나이다), 9,9-비스페놀 플로레닐, 9,9-비스(4'-에톡시페닐) 플로레닐로 이루어지는 군으로부터 선택되는 어느 하나이다.X is alkylene of _{C 1 ~ C 10, - (} CH 2 CH 2 O) nCH 2 CH 2 - ,-(CHCH ₃ CH ₂ ) nOCHCH ₃ CH _2- , where n is an integer from 1 to 10,

(Wherein Z is a direct bond or C ₁ to C ₆ alkylene, ketone, -O-, -S-, -SO _2- , hexafluoropropylene, -OC ₆ H ₄ O-, -OC ₆ H ₄ C (CH ₃ ) ₂ C ₆ H ₄ O-), 9,9-bisphenol florenyl, 9,9-bis (4'-ethoxyphenyl) florenyl selected from the group consisting of Which is either.

Y is a divalent group derived from a compound produced by a ring-opening polymerization reaction of an alcohol group of a compound formed through a condensation reaction of an acid anhydride with a diglycidyl ether compound and a (meth) acrylic acid.

The acid anhydride is represented by the following formula (2).

In Formula 2,

A is selected from hydrogen, C ₁ -C ₆ alkoxy, phenoxy, C ₁ ~ C ₁₀ alkyl unsubstituted or substituted with halogen, C ₂ ~ C ₁₀ alkenes and phenyl containing 1 to 3 unsaturated groups ego,

B is hydrogen, C ₁ -C ₆ alkoxy, phenoxy, C ₁ ~ C ₁₀ alkylene unsubstituted or substituted with halogen, C ₁ ~ C ₁₀ alkenylene and phenylene containing 1 to 3 unsaturated groups One selected from among, A and B may be connected to form a 5 to 6 angular ring.

Specific examples of the acid anhydride include succinic anhydride, glutaric anhydride, methyl succinic anhydride, maleic anhydride, methyl maleic anhydride, phthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, 3,4,5,6 One or more selected from the group consisting of -tetrahydrophthalic anhydride, hexahydrophthalic anhydride, cis-5-norbornene- (endo, exo) -2,3-dicarboxylic acid anhydride and the like can be used.

B) The epoxy resin is a compound that provides a) an epoxy group capable of alternating copolymerization with a diacid compound having two polymerizable unsaturated groups, and is a compound having two epoxy groups in one molecule.

Specific examples of the epoxy resins include bisphenol A epoxy resins, hydrogenated bisphenol A epoxy resins, bisphenol F epoxy resins, hydrogenated bisphenol F epoxy resins, novolac epoxy resins, aromatic epoxy resins, and glycidyl esters. Aliphatic, cycloaliphatic, or aromatic epoxy compounds other than the above-mentioned resins, glycidyl amine resins, brominated derivatives of such epoxy resins, epoxy resins and brominated derivatives thereof, and the like. It is selected above, Preferably it is bisphenol-A resin.

Preferably, the a) diacid compound having two polymerizable unsaturated groups and b) the epoxy resin are mixed in a molar ratio of 1: 0.3 to 1.1. When the molar ratio of a) the diacid compound having two polymerizable unsaturated groups and b) the epoxy resin is less than 1: 0.3, the molecular weight is small, so that the binding function between the components required as the binder polymer is weak, and withstands the physical external force during development. The pattern is lost, and physical properties such as heat resistance and chemical resistance cannot be satisfied. If the molar ratio is greater than 1: 1.1, the molecular weight is increased to increase the viscosity, which may lower the process characteristics.

The solvent c) is not limited as long as it does not include an alcohol group and has a boiling point that is not easily volatilized at the condensation reaction temperature.

Specific examples of the c) solvent include methyl ethyl ketone, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol dimethyl ether, propylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol Methyl ethyl ether, dipropylene glycol dimethyl ether, cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, 3-methoxybutyl acetate, ethyl 3-ethoxypropionate, ethyl cellosolve At least one selected from the group consisting of acetate, methyl cellosolve acetate, propyl cellosolve acetate, butyl cellosolve acetate, and butyl acetate can be used.

The composition for producing an alkali-soluble resin according to the present invention may further include an acid anhydride as necessary. The acid anhydride may serve to form an acid group by reacting with an alcohol group formed by a condensation reaction between a) a diacid compound having two polymerizable unsaturated groups and b) an epoxy resin.

The acid anhydride is as defined in Formula 2, specific examples of the acid anhydride, succinic anhydride, glutaric anhydride, methyl succinic anhydride, maleic anhydride, methyl maleic anhydride, phthalic anhydride, 1,2,3,6- Tetrahydrophthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, hexahydrophthalic anhydride, cis-5-norbornene- (endo, exo) -2,3-dicarboxylic anhydride, and the like. One or more selected species may be used.

It is preferable that 5-50 mol% of said acid anhydrides are added with respect to the composition for alkali-soluble resin manufacture. The acid value may be increased depending on the amount of the acid anhydride added, but when it exceeds 50 mol%, the alkali-soluble resin produced may have a deteriorated physical and chemical strength required as the photosensitive resin.

In another embodiment of the present invention, (i) mixing a) a diacid compound having two polymerizable unsaturated groups and b) an epoxy resin in a molar ratio of 1: 0.3 to 1.1 in a solvent; And (ii) heating the mixture prepared in step (iii) at 80 to 130 ° C. for 4 to 24 hours.

A polymer compound is formed by alternating copolymerization reaction of a) a diacid compound having two polymerizable unsaturated groups and b) an epoxy resin. The said high molecular compound can be manufactured in consideration of molecular weight and an acid value according to the use of alkali-soluble resin.

The solvent used in the reaction is not an alcohol group and is not limited as long as it is a solvent having a boiling point higher than the reaction temperature.

The reaction concentration can be selected in the range of 10 to 100 wt%. Considering that the reaction is a condensation reaction, the higher the reaction concentration, the better the yield of the reaction, but considering the risk of gelation that may occur during the reaction, the load on the impeller of the reactor, and the ease of operation of the reaction solution after the reaction. More preferably 30 to 80 wt%.

The composition for producing the alkali-soluble resin may be adjusted to the acid value through the condensation reaction after addition of an acid anhydride, if necessary.

When the acid anhydride is added, the reaction temperature is preferably adjusted to 70 to 110 ° C., and the reaction time is preferably stirred for 4 to 24 hours. Under the reaction temperature conditions, since the ethylene group added through the condensation reaction may cause gelation through thermal polymerization, a thermal polymerization inhibitor suitable for the polymerization reaction may be used under an oxygen atmosphere, and a representative example of the thermal polymerization inhibitor is 4-methoxyphenol (MEHQ) and 2,6-di-thibutyl-4-methyl phenol and the like can be used.

As a catalyst that can be used in the present invention, a conventional catalyst known in the art as a catalyst for condensation reaction can be used, and for example, a basic catalyst such as alkylammonium salt, triphenylphosphine, triphenylantimony or dimethylaminopyridine can be used. Can be.

Alkali-soluble resin of the present invention prepared by the above production method does not use acid dianhydride, compared to the conventional condensation polymerization resin, high storage stability, long-term storage is easy, and sensitivity and adhesion is improved. The photosensitive composition including the alkali-soluble resin also has high storage stability and excellent sensitivity and adhesiveness.

As another embodiment of the present invention, an alkali-soluble resin formed from the composition for producing an alkali-soluble resin is provided.

The alkali-soluble resin may be represented by the following formula (3).

R, X and Y are the same as defined in Chemical Formulas 1 and 2,

Z is a divalent group derived from a compound produced by reacting one or two or more compounds selected from an acid group of Formula 1 and an epoxy resin or a derivative thereof.

Specific examples of the epoxy resin or derivatives thereof include bisphenol A epoxy resin, hydrogenated bisphenol A epoxy resin, bisphenol F epoxy resin, hydrogenated bisphenol F epoxy resin, novolac epoxy resin, aromatic epoxy resin and glycidyl. Ester resins, glycidyl amine resins, brominated derivatives of such epoxy resins, epoxy resins and aliphatic, cycloaliphatic or aromatic epoxy compounds other than the brominated derivatives thereof, and the like, and preferably bisphenol A resins.

The acid value of the alkali-soluble resin prepared according to the above method is preferably in the range of 30 to 200 KOH mg / g.

If the acid value of the alkali-soluble resin is less than 30, the solubility in the alkaline developer is low, there is a fear that the development time is long, leaving a residue on the substrate, if the acid value of the alkali-soluble resin exceeds 200, the desorption of the pattern occurs and the pattern of Straightness cannot be secured and the taper angle of the pattern will show an inverse taper (or T-top) over 90 degrees.

Moreover, as a weight average molecular weight of the said alkali-soluble resin, the range of 1,000-200,000 is preferable, and the range of 3,000-30,000 is more preferable.

When the weight average molecular weight of the alkali-soluble resin is less than 1,000, the binding function between the components required as the binder polymer is weak, and the pattern is lost because it cannot withstand the physical external force during development, and the basic heat resistance and chemical resistance required for the color filter pattern, etc. Physical properties cannot be satisfied. When the weight average molecular weight of the alkali-soluble resin exceeds 200,000, the developability of the alkali developing solution is excessively low, so that the development process characteristics are deteriorated, and when it is severe, the development is impossible, and the flowability is also deteriorated to control the coating thickness or uniformity ( It is difficult to secure uniformity.

Moreover, as another embodiment of this invention,

1) alkali-soluble resin according to the present invention;

2) a polymerizable compound having an ethylenically unsaturated bond;

3) photopolymerization initiator; And

4) solvent

It provides a photosensitive resin composition comprising a.

Among the constituents of the photosensitive resin composition according to the present invention, the above-mentioned 1) alkali-soluble resin according to the present invention preferably contains 1 to 20 parts by weight based on 100 parts by weight of the total photosensitive resin composition. When the content of the alkali-soluble resin is less than 1 part by weight or more than 20 parts by weight, the viscosity of the prepared ink composition is too low or high, making it difficult to maintain uniformity of the film during coating.

Among the constituents of the photosensitive resin composition according to the present invention, non-limiting examples of the polymerizable compound having 2) ethylenically unsaturated bonds include ethylene glycol di (meth) acrylate and polyethylene glycol di with 2 to 14 ethylene groups. (Meth) acrylate, trimethylolpropane di (meth) acrylate, trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, 2-trisacryloyl Polyhydric alcohols such as oxymethylethylphthalic acid, propylene glycol di (meth) acrylate having 2 to 14 propylene groups, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, and the like. A compound obtained by esterification with an unsaturated carboxylic acid; A compound obtained by adding (meth) acrylic acid to a compound containing a glycidyl group such as trimethylolpropane triglycidyl ether acrylic acid adduct and bisphenol A diglycidyl ether acrylic acid adduct; Ester compound of the compound which has hydroxyl group or ethylenically unsaturated bond, such as phthalic acid diester of (beta) -hydroxyethyl (meth) acrylate and toluene diisocyanate adduct of (beta) -hydroxyethyl (meth) acrylate, and polyhydric carboxylic acid Or adducts with polyisocyanates; (Meth) acrylic-acid alkylesters, such as methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, and 2-ethylhexyl (meth) acrylate, and 9,9'-bis [4- (2 -Acryloyloxyethoxy) phenyl] fluorene, but not limited to these, those known in the art can be used. In some cases, silica dispersions may be used for these compounds, for example, Nanocryl XP series (0596, 1045, 21/1364) and Nanopox XP series (0516, 0525) manufactured by Hanse Chemie.

It is preferable that the said polymeric compound which has b) ethylenically unsaturated bond contains 0.5-30 weight part with respect to 100 weight part of photosensitive resin compositions. If the amount of use is less than 0.5 parts by weight, the strength of the pattern is lowered, and if it exceeds 30 parts by weight, the adhesiveness of the resin layer is excessive and foreign matters are easily attached.

Among the constituents of the photosensitive resin composition according to the present invention, non-limiting examples of the 3) photopolymerization initiator include 2,4-trichloromethyl- (4'-methoxyphenyl) -6-triazine, 2,4-tri Chloromethyl- (4'-methoxystyryl) -6-triazine, 2,4-trichloromethyl- (piflonyl) -6-triazine, 2,4-trichloromethyl- (3 ', 4 Triazine compounds such as' -dimethoxyphenyl) -6-triazine and 3- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} propanoic acid; Bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis (2,3- , 5'-tetraphenylbiimidazole; Methyl-1-phenylpropan-1-one, 1- (4-isopropylphenyl) -2-hydroxy- (4-methylthiophenyl) -2-morpholinocarboxylate, 2-methoxy-2-phenylacetophenone, (Irgacure-907), 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) 369); O-acyloxime compounds such as Irgacure OXE 01 and Irgacure OXE 02 from Ciba Geigy; Benzophenone compounds such as 4,4'-bis (dimethylamino) benzophenone and 4,4'-bis (diethylamino) benzophenone; Thioxanthone compounds such as 2,4-diethylthioxanthone, 2-chlorothioxanthone, isopropylthioxanthone and diisopropylthioxanthone; 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis (2,6-dimethoxybenzoyl) -2,4,4-trimethylpentylphosphine oxide, bis (2,6-dichlorobenzoyl) propylphosphine oxide Phosphine oxide-based compounds; 3,3'-carbonylvinyl-7- (diethylamino) coumarin, 3- (2-benzothiazolyl) -7- (diethylamino) coumarin, 3-benzoyl-7- (diethylamino) coumarin, 3-benzoyl-7-methoxy-coumarin, 10,10'-carbonylbis [1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H, 5H, 11H-Cl] Coumarin-based compounds such as -benzopyrano [6,7,8-ij] -quinolizin-11-one; and the like.

It is preferable that said c) photoinitiator contains 0.1-5 weight part with respect to 100 weight part of photosensitive resin compositions. When the content of the photopolymerization initiator is less than 0.1 part by weight, the degree of participation in curing of the polymerizable compound having an ethylenically unsaturated bond is reduced, and when it exceeds 5 parts by weight, radicals that do not participate in curing may cause contamination of the composition.

Among the constituents of the photosensitive resin composition according to the present invention, non-limiting examples of the solvent 4) methyl ethyl ketone, methyl cellosolve, ethyl cellosolve, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol dimethyl Ether, propylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, 2-ethoxy propanol, 2-methoxy propanol, 3-methoxy butanol, cyclohexanone, Cyclopentanone, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, 3-methoxybutyl acetate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, dipropylene glycol mono Methyl ether or mixtures of one or more thereof.

It is preferable that the said d) solvent contains 10-95 weight part with respect to 100 weight part of photosensitive resin compositions.

The photosensitive resin composition of the present invention may additionally include one or more additives such as alkali-soluble acrylic copolymer resins, photosensitizers, colorants, curing accelerators, thermal polymerization inhibitors, plasticizers, adhesion promoters, fillers, or surfactants. .

As the colorant, one or more pigments, dyes or mixtures thereof may be used. Specifically, as the black pigment, a metal oxide such as carbon black, graphite, or titanium black may be used. Examples of carbon black include cysto 5HIISAF-HS, cysto KH, cysto 3HHAF-HS, cysto NH, cysto 3M, cysto 300HAF-LS, cysto 116HMMAF-HS, cysto 116MAF, cysto FMFEF-HS , Sisto SOFEF, Sisto VGPF, Sisto SVHSRF-HS and Sisto SSRF (Donghae Carbon Co., Ltd.); Diagram Black II, Diagram Black N339, Diagram Black SH, Diagram Black H, Diagram LH, Diagram HA, Diagram SF, Diagram N550M, Diagram M, Diagram E, Diagram G, Diagram R, Diagram N760M, Diagram LR, # 2700, # 2600, # 2400, # 2350, # 2300, # 2200, # 1000, # 980, # 900, MCF88, # 52, # 50, # 47, # 45, # 45L, # 25, # CF9, # 95, # 3030, # 3050, MA7, MA77, MA8, MA11, MA100, MA40, OIL7B, OIL9B, OIL11B, OIL30B and OIL31B (Mitsubishi Chemical Corporation); PRINTEX-25, PRINTEX-25, PRINTEX-55, PRINTEX-55, PRINTEX-45, PRINTEX-35, PRINTEX- 200, PRINTEX-40, PRINTEX-30, PRINTEX-3, PRINTEX-A, SPECIAL BLACK-550, SPECIAL BLACK-350, SPECIAL BLACK-250, SPECIAL BLACK-100 and LAMP BLACK-101 (Daegu; RAVEN-1100ULTRA, RAVEN-1080ULTRA, RAVEN-1060ULTRA, RAVEN-1040, RAVEN-1035, RAVEN-1020, RAVEN-1000, RAVEN-890H, RAVEN-890, RAVEN-880ULTRA, RAVEN-860ULTRA, RAVEN-850, RAVEN- 820, RAVEN-790ULTRA, RAVEN-780ULTRA, RAVEN-760ULTRA, RAVEN-520, RAVEN-500, RAVEN-460, RAVEN-450, RAVEN-430ULTRA, RAVEN-420, RAVEN-410, RAVEN-2500ULTRA, RAVEN-2000, RAVEN-1500, RAVEN-1255, RAVEN-1250, RAVEN-1200, RAVEN-1190ULTRA, RAVEN-1170 (Colombia Carbon, Inc.) or mixtures thereof.

Examples of coloring agents that can be colored include carmine 6B (CI12490), phthalocyanine green (CI 74260), phthalocyanine blue (CI 74160), perylene black (BASF K0084. K0086), cyanine black, lino yellow (CI 21090) Linol Yellow GRO (CI 21090), Benzidine Yellow 4T-564D, Victoria Pure Blue (CI42595), CI PIGMENT RED 3, 23, 97, 108, 122, 139, 140, 141, 142, 143, 144, 149, 166, 168, 175, 177, 180, 185, 189, 190, 192, 220, 221, 224, 230, 235, 242, 254, 255, 260, 262, 264, 272; C.I. PIGMENT GREEN 7, 36; C.I. PIGMENT blue 15: 1, 15: 3, 15: 4, 15: 6, 16, 22, 28, 36, 60, 64; C.I. PIGMENT yellow 13, 14, 35, 53, 83, 93, 95, 110, 120, 138, 139, 150, 151, 154, 175, 180, 181, 185, 194, 213; C.I. PIGMENT VIOLET 15, 19, 23, 29, 32, 37, etc. In addition, white pigments and fluorescent pigments can be used.

Examples of the curing accelerator include 2-mercaptobenzoimidazole, 2-mercaptobenzothiazole, 2-mercaptobenzoxazole, 2,5-dimercapto-1,3,4-thiadiazole, 2-mer Capto-4,6-dimethylaminopyridine, pentaerythritol tetrakis (3-mercaptopropionate), pentaerythritol tris (3-mercaptopropionate), pentaerythritol tetrakis (2-mercaptoacetate), penta Erythritol tris (2-mercaptoacetate), trimethylolpropane tris (2-mercaptoacetate), trimethylolpropane tris (3-mercaptopropionate), trimethylolethane tris (2-mercaptoacetate), trimethyljade One or more selected from the group consisting of ethane tris (3-mercaptopropionate) may be used, but not limited thereto, and those known in the art may be used.

The thermal polymerization inhibitors include p-anisole, hydroquinone, pyrocatechol, t-butyl catechol, N-nitrosophenylhydroxyamine ammonium salt, N-nitrosophenylhydroxy One or more kinds selected from the group consisting of amine aluminum salts and phenothiazines may be used, but are not limited thereto, and those known in the art may be used.

Other plasticizers, adhesion promoters, fillers, surfactants and the like can also be used for all compounds that can be included in conventional photosensitive resin compositions.

When the above-mentioned additives other than the alkali-soluble resin are added, the colorant in the additive is 0.5 to 20 parts by weight, and the remaining additives are 0.01 to 10 parts by weight based on 100 parts by weight of the photosensitive resin composition. It is preferable to contain.

As another embodiment of this invention, the hardened | cured material formed from the said photosensitive resin composition is provided.

Specific examples of the cured product include, but are not limited to, a red, green, blue pattern or black matrix pattern and column spacer of a color filter.

The photosensitive resin composition of the present invention is used in a roll coater, curtain coater, spin coater, spin coater, slot die coater, various printing, deposition, and the like, and supports for metal, paper, and glass plastic substrates. Can be applied to the phase. Moreover, it is also possible to transfer on other support bodies after apply | coating on support bodies, such as a film, and the application method is not specifically limited.

As a light source for hardening the photosensitive resin composition of this invention, mercury vapor arc (arc), carbon arc, Xe arc etc. which emit light of 250-450 nm in wavelength, for example are mentioned.

The present invention will be described in more detail with reference to the following examples. However, the Examples are provided to illustrate the present invention and the scope of the present invention is not limited thereto.

Synthetic example : Alkali Soluble Resin Manufacture

Synthetic example  One

450.2 g of 9,9-bisphenolfluorene diglycidyl ether, 140.7 g of acrylic acid, 1.7 g of tetrabutylammonium bromide, 0.2 g of 2,6-t-butyl-4-methylphenol, 592.2 g of PGMEA were placed in a 2 L reactor. Put and stirred using a mechanical stirrer. The reactor was heated to 110 ° C. while flowing oxygen inside the reactor. After heating for 15 hours, the reaction was terminated to obtain a solution of 9,9-bisphenolfluorene diglycerate diacrylate (solid content of 50.8%). 8 g of tetrahydrophthalic anhydride and 8 g of PGMEA were added to 34 g of the solution thus prepared, and reacted at 115 ° C. for 12 hours. Subsequently, 6.6 g of bisphenol A epoxy resin and 19.8 g of PGMEA were added thereto, and further reacted at 115 ° C. for 10 hours to complete alkali-soluble resin solution 1 of the present invention. (44.5% solids, acid value 33, molecular weight 10,900)

Synthetic example  2

42 g of tetrahydrophthalic anhydride and 42 g of PGMEA were added to 166 g of a solution of 9,9-bisphenolfluorene diglycerate diacrylate prepared as in Synthesis Example 1, and reacted at 115 ° C. for 12 hours. Subsequently, 30.5 g of bisphenol A epoxy resin and 163.1 g of PGMEA were added thereto, and further reacted at 115 ° C. for 10 hours to complete alkali-soluble resin solution 2 of the present invention. (34.2% solids, acid value 47, molecular weight 7,800)

Synthetic example  3

42 g of tetrahydrophthalic anhydride and 42 g of PGMEA were added to 166 g of a solution of 9,9-bisphenolfluorene diglycerate diacrylate prepared as in Synthesis Example 1, and reacted at 115 ° C. for 12 hours. Subsequently, 21 g of bisphenol A epoxy resin and 145 g of PGMEA were added thereto, and further reacted at 115 ° C. for 10 hours to complete alkali-soluble resin solution 3 of the present invention. (Solid content 33.4%, acid value 70.6, molecular weight 3,500)

Synthetic example  4

8.4 g of tetrahydrophthalic anhydride and 8.4 g of PGMEA were added to 33 g of a solution of 9,9-bisphenolfluorene diglycerate diacrylate prepared as in Synthesis Example 1, and reacted at 115 ° C. for 12 hours. Subsequently, 5 g of bisphenol A epoxy resin and 22.6 g of PGMEA were added thereto, followed by reaction at 115 ° C. for 10 hours to further react 2 g of tetrahydrophthalic anhydride to complete alkali-soluble resin solution 4 of the present invention. (Solid content 45.9%, acid value 70.3, molecular weight 6,000)

synthesis Comparative example  One

To 106.74 g of a solution of 9,9-bisphenolfluorene diglycerate diacrylate prepared as in Synthesis Example 1, 19.22 g of biphenyltetracarboxylic dianhydride and 22.48 g of PGMEA were added and reacted at 115 ° C. for 9 hours. Example Alkali-soluble resin solution 1 was completed. (50.3% solids, acid value 114, molecular weight 5,000)

synthesis Comparative example  2

To 106.30 g (solid content of 50.8%) of 9,9-bisphenolfluorene diglycerate diacrylate prepared in Comparative Example 1 above, 17.83 g of biphenyltetracarboxylic dianhydride, 2.03 g of tetrahydrophthalic anhydride, and 22.70 g of PGMEA Was added and reacted at 115 ° C. for 9 hours to complete Comparative Example Resin Solution 2. (50.0% solids, acid value 118, molecular weight 3,900)

Example  : Photosensitive Resin Composition

Example  One

35 g of carbon black 25% dispersion, 13.4 g of alkali-soluble resin (solid content 3.5 g) prepared in Synthesis Example 1 as alkali-soluble resin, 3.5 g of dipentaerythritol hexaacrylate as a polymerizable compound, 2.5 g of photopolymerization initiator Irgacure-369 , 1 g of 3- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} propanoic acid, 0.5 g of 4,4'-bis (diethylamino) benzophenone, 44.5 g of PGMEA, an organic solvent, was mixed for 3 hours to prepare a photosensitive resin composition.

Example  2

35 g of 25% dispersion of carbon black, 11.7 g (solid content 3.5 g) of alkali-soluble resin prepared in Synthesis Example 2 as alkali-soluble resin, 3.5 g of dipentaerythritol hexaacrylate as a polymerizable compound, photopolymerization initiator Irgacure-369 2.5 g, 3- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} propanoic acid 1 g, 4,4'-bis (diethylamino) benzophenone 0.5 g, 45.8 g of an organic solvent, PGMEA, were mixed for 3 hours to prepare a photosensitive resin composition.

Example  3

35 g of carbon black 25% dispersion, 13.0 g of alkali-soluble resin (solid content 3.5 g) prepared in Synthesis Example 3 as alkali-soluble resin, 3.5 g of dipentaerythritol hexaacrylate as a polymerizable compound, photopolymerization initiator Irgacure-369 2.5 g, 3- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} propanoic acid 1 g, 4,4'-bis (diethylamino) benzophenone 0.5 g, 48.75 g of an organic solvent, PGMEA, was mixed for 3 hours to prepare a photosensitive resin composition.

Example  4

35 g of 25% dispersion of carbon black, 13 g of alkali-soluble resin (solid content 3.5 g) prepared in Synthesis Example 4 as alkali-soluble resin, 3.5 g of dipentaerythritol hexaacrylate as a polymerizable compound, 2.5 g of photopolymerization initiator Irgacure-369 , 1 g of 3- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} propanoic acid, 0.5 g of 4,4'-bis (diethylamino) benzophenone 48.75 g of an organic solvent, PGMEA, was mixed for 3 hours to prepare a photosensitive resin composition.

Comparative example  One

A photosensitive resin composition was prepared in the same manner as in Example 1, except that 13.4 g of the resin of Comparative Synthesis Example 1 was used as the alkali-soluble resin.

Comparative example  2

A photosensitive resin composition was prepared in the same manner as in Example 4, except that 12.5 g of the resin of Comparative Synthesis Example 2 was used as the alkali-soluble resin.

Experimental Example

Molecular Weight Stability Evaluation Method

The molecular weights of the photosensitive resin composition solutions prepared in Examples 1 to 4 and Comparative Examples 1 and 2 were measured within 24 hours of preparing using gel permeation chromatography (GPC). After that, each photosensitive resin composition was divided into two parts, and then stored separately at conditions of room temperature (20 ° C.) and high temperature (45 ° C.), and after 7 days of manufacture, the molecular weight was again measured through GPC. Compared with the initial molecular weight and the molecular weight after one week, especially when the increase in molecular weight of less than 10% in the high temperature accelerated experiment, excellent, 10 to 20% increased good, 20% or more was judged to be poor. Shown in

[Table 1]

As shown in Table 1, the alkali-soluble resin of the present invention was excellent in storage stability at room temperature (20 ° C.) and high temperature (45 ° C.), so that storage was easy and long-term storage was possible. Of course, the effects of the present invention are not limited to the above-mentioned room temperature and high temperature.

Evaluation of Sensitivity and Chemical Resistance of Photosensitive Resin Composition

The following method was used to test the sensitivity and chemical resistance of the photosensitive resin composition prepared according to the present invention.

The photosensitive resin composition solutions prepared by Examples 1 to 4 and Comparative Examples 1 and 2 were spin coated on glass, respectively, and prebakeed at about 100 ° C. for 2 minutes to form a film. Each formed film was exposed to an energy of 100 mJ / cm 2 under a high-pressure mercury lamp using a photomask, and then the pattern was developed over time using an aqueous KOH alkali solution of pH 11.3 to 11.7. And washed with deionized water. Then, postbake was performed at 220 ° C. for about 30 minutes.

The sensitivity of each photosensitive resin composition was determined using the minimum pixel size remaining after development when exposed using a Line & space mask.

The chemical resistance of each photosensitive resin composition was determined by a change in thickness after immersion in 60 ° C. NMP (N-methyl pyrrolidone) for 3 minutes in the case of a black matrix photosensitive agent.

The experimental results for the sensitivity and chemical resistance are shown in Table 2 below.

In addition, after the pattern was formed to measure the development margin, the development was carried out for a predetermined time with a developing solution, and the size of the remaining pattern was measured and shown in Table 3.

[Table 2] Application result of black matrix photoresist

As shown in Table 2, as a result of applying the photosensitive resin compositions of Examples 1 to 4 of the present invention to the black matrix photoresist, the minimum pixel size remaining after development was 5 to 10 μm, compared to 15 μm of Comparative Examples 1 and 2 Low sensitivity can be confirmed. In addition, the thickness change after immersion in NMP for 3 minutes shows 1.2 to 2.0%, it can be seen that the chemical resistance to chemicals is higher than 2.9 to 3.1% of Comparative Examples 1 and 2.

Table 3 Application Results for Black Matrix Photoresist

As shown in Table 3, as a result of applying the photosensitive resin compositions of Examples 1 to 4 of the present invention to the black matrix photosensitive agent, it can be confirmed that the development margin and the adhesion to the glass substrate are excellent in comparison with the comparative example.

1 to 4 are NMR (Nuclear Magnetic Resonance) data of alkali-soluble resins according to Synthesis Examples 1 to 4 of the present invention.

Claims (27)

delete a) a diacid compound having two polymerizable unsaturated groups, b) an epoxy resin and c) a solvent, The composition for producing an alkali-soluble resin, wherein a) the diacid compound having two polymerizable unsaturated groups is a compound represented by the following general formula (1): [Formula 1]

In Formula 1, R is hydrogen or methyl, X is alkylene of _{C 1 ~ C 10, - (} CH 2 CH 2 O) nCH 2 CH 2 - ,-(CHCH ₃ CH ₂ ) nOCHCH ₃ CH _2- , where n is an integer from 1 to 10,

(Wherein Z is a direct bond or C ₁ to C ₆ alkylene, ketone, -O-, -S-, -SO _2- , hexafluoropropylene, -OC ₆ H ₄ O-, -OC ₆ H ₄ C (CH ₃ ) ₂ C ₆ H ₄ O-), or from the group consisting of 9,9-bisphenol florenyl and 9,9-bis (4'-ethoxyphenyl) florenyl Which one is chosen, Y is a divalent group derived from a compound produced by a ring-opening polymerization reaction of an alcohol group of a compound formed through a condensation reaction of an acid anhydride with a diglycidyl ether compound and a (meth) acrylic acid. The composition for preparing an alkali-soluble resin according to claim 2, wherein the acid anhydride is represented by the following Chemical Formula 2: [Formula 2]

In Formula 2, A is selected from hydrogen, C ₁ -C ₆ alkoxy, phenoxy, C ₁ ~ C ₁₀ alkyl unsubstituted or substituted with halogen, C ₂ ~ C ₁₀ alkenes and phenyl containing 1 to 3 unsaturated groups ego, B is hydrogen, C ₁ -C ₆ alkoxy, phenoxy, C ₁ ~ C ₁₀ alkylene unsubstituted or substituted with halogen, C ₁ ~ C ₁₀ alkenylene and phenylene containing 1 to 3 unsaturated groups One selected from among, A and B may be connected to form a 5 to 6 angular ring. The epoxy resin of claim 2, wherein the epoxy resin is a bisphenol A epoxy resin, a hydrogenated bisphenol A epoxy resin, a bisphenol F epoxy resin, a hydrogenated bisphenol F epoxy resin, a novolac epoxy resin, an aromatic epoxy resin, or glycy. It is one or two or more selected from the group consisting of diyl ester resins, glycidyl amine resins, brominated derivatives of such epoxy resins, epoxy resins and aliphatic, cycloaliphatic or aromatic epoxy compounds other than the brominated derivatives thereof. Alkali-soluble resin manufacturing composition. The composition for producing an alkali-soluble resin according to claim 2, wherein a) a diacid compound having two polymerizable unsaturated groups and b) an epoxy resin are mixed in a 1: 0.3 to 1.1 molar ratio. The method of claim 2, wherein c) the solvent is methyl ethyl ketone, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol dimethyl ether, propylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, di Ethylene glycol methyl ethyl ether, dipropylene glycol dimethyl ether, cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, 3-methoxybutyl acetate, ethyl 3-ethoxypropionate, ethyl The composition for producing alkali-soluble resin, characterized in that at least one selected from the group consisting of cellosolve acetate, methyl cellosolve acetate, propyl cellosolve acetate, butyl cellosolve acetate, and butyl acetate. The composition for producing an alkali-soluble resin according to claim 2, wherein the composition for producing an alkali-soluble resin further comprises an acid anhydride. The method of claim 7, wherein the acid anhydride is succinic anhydride, glutaric anhydride, methyl succinic anhydride, maleic anhydride, methyl maleic anhydride, phthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, 3,4, Alkali soluble, characterized in that at least one selected from the group consisting of 5,6-tetrahydrophthalic anhydride, hexahydrophthalic anhydride and cis-5-norbornene- (endo, exo) -2,3-dicarboxylic anhydride Resin manufacturing composition. (Iii) mixing a) a diacid compound having two polymerizable unsaturated groups and b) an epoxy resin in a molar ratio of 1: 0.3 to 1.1 in a solvent; And (ii) heating the mixture prepared in step (iii) at 80 to 130 ° C. for 4 to 24 hours, The method for producing an alkali-soluble resin, wherein a) the diacid compound having two polymerizable unsaturated groups is a compound represented by the following general formula (1): [Formula 1]

In Formula 1, R is hydrogen or methyl, X is alkylene of _{C 1 ~ C 10, - (} CH 2 CH 2 O) nCH 2 CH 2 - ,-(CHCH ₃ CH ₂ ) nOCHCH ₃ CH _2- , where n is an integer from 1 to 10,

(Wherein Z is a direct bond or C ₁ to C ₆ alkylene, ketone, -O-, -S-, -SO _2- , hexafluoropropylene, -OC ₆ H ₄ O-, -OC ₆ H ₄ C (CH ₃ ) ₂ C ₆ H ₄ O-), or from the group consisting of 9,9-bisphenol florenyl and 9,9-bis (4'-ethoxyphenyl) florenyl Which one is chosen, Y is a divalent group derived from a compound produced by a ring-opening polymerization reaction of an alcohol group of a compound formed through a condensation reaction of an acid anhydride with a diglycidyl ether compound and a (meth) acrylic acid. 10. The method of claim 9, wherein the acid dianhydride is added after step (ii) and reacted at 70 to 110 ° C. for 4 to 24 hours. 11. An alkali-soluble resin represented by the following general formula (3) formed from the composition for producing an alkali-soluble resin of any one of claims 2 to 8. (3)

R, X and Y are as defined in Formula 2 of claim 2, Z is a divalent group derived from a compound produced by reacting one or two or more compounds selected from the acid group of Formula 1 and epoxy resin or derivatives thereof of claim 2. The alkali-soluble resin according to claim 11, wherein the acid value of the alkali-soluble resin is 30 to 200 KOH mg / g. The alkali-soluble resin of claim 11, wherein the weight average molecular weight of the alkali-soluble resin is 1,000 to 200,000. The method of claim 11, wherein the epoxy resin or derivatives thereof are bisphenol A epoxy resin, hydrogenated bisphenol A epoxy resin, bisphenol F epoxy resin, hydrogenated bisphenol F epoxy resin, novolac epoxy resin, aromatic epoxy resin, glyc Alkali-soluble resin characterized by being an aliphatic, cycloaliphatic, or aromatic epoxy compound other than a cydyl ester resin, a glycidyl amine resin, a brominated derivative of such an epoxy resin, an epoxy resin, and a brominated derivative thereof. 1) alkali-soluble resin according to claim 11; 2) a polymerizable compound having an ethylenically unsaturated bond; 3) photopolymerization initiator; And 4) solvent Photosensitive resin composition comprising a. The photosensitive resin composition of claim 15, wherein the 1) alkali-soluble resin includes 1 to 20 parts by weight based on 100 parts by weight of the photosensitive resin composition. The polymerizable compound of claim 2, wherein the polymerizable compound having an ethylenically unsaturated group includes ethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate having a number of ethylene groups of 2 to 14, and trimethylolpropane di (meth). Acrylate, trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, 2-trisacryloyloxymethylethylphthalic acid, the number of propylene groups being 2 to 14 Compounds obtained by esterifying propylene glycol di (meth) acrylate, dipentaerythritol penta (meth) acrylate or dipentaerythritol hexa (meth) acrylate with α, β-unsaturated carboxylic acid; Compounds obtained by adding (meth) acrylic acid to a trimethylolpropane triglycidyl ether acrylic acid adduct or a bisphenol A diglycidyl ether acrylic acid adduct; phthalic acid diester of β-hydroxyethyl (meth) acrylate or toluene diisocyanate adduct of β-hydroxyethyl (meth) acrylate with an ester compound of polyhydric carboxylic acid, or an adduct of polyisocyanate; Methyl (meth) acrylate; Ethyl (meth) acrylate; Butyl (meth) acrylate; 2-ethylhexyl (meth) acrylate; And 9,9'-bis [4- (2-acryloyloxyethoxy) phenyl] fluorene. The photosensitive resin composition, wherein the compound is any one selected from the group consisting of The photosensitive resin composition according to claim 15, wherein the polymerizable compound having an ethylenically unsaturated group includes 0.5 to 30 parts by weight based on 100 parts by weight of the photosensitive resin composition. The method according to claim 15, wherein the 3) photopolymerization initiator is 2,4-trichloromethyl- (4'-methoxyphenyl) -6-triazine, 2,4-trichloromethyl- (4'-methoxystyryl) -6-triazine, 2,4-trichloromethyl- (piflonil) -6-triazine, 2,4-trichloromethyl- (3 ', 4'-dimethoxyphenyl) -6-triazine, 3- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} propanoic acid, 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenyl biimidazole, 2,2'-bis (2,3-dichlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2-hydroxy-2-methyl -1-phenylpropan-1-one, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 4- (2-hydroxyethoxy) -phenyl (2-hydroxy Roxy) propyl ketone, 1-hydroxycyclohexyl phenyl ketone, 2,2-dimethoxy-2-phenyl acetophenone, 2-methyl- (4-methylthiophenyl) -2-morpholino-1-propane-1 Irgacure-907, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one; Irgacure OXE 01 (Ciba Geigy), Irgacure OXE 02 (Ciba Geigy), 4,4'-bis (dimethylamino) benzophenone, 4,4'-bis (diethylamino) benzophenone, 2,4-di Ethyl thioxanthone, 2-chloro thioxanthone, isopropyl thioxanthone, diisopropyl thioxanthone, 2,4,6-trimethylbenzoyl diphenylphosphine oxide, bis (2,6-dimethoxybenzoyl)- 2,4,4-trimethylpentyl phosphine oxide, bis (2,6-dichlorobenzoyl) propyl phosphine oxide, 3,3'-carbonylvinyl-7- (diethylamino) coumarin, 3- (2-benzo Thiazolyl) -7- (diethylamino) coumarin, 3-benzoyl-7- (diethylamino) coumarin, 3-benzoyl-7-methoxy-coumarin, 10,10'-carbonylbis [1,1, Group consisting of 7,7-tetramethyl-2,3,6,7-tetrahydro-1H, 5H, 11H-Cl] -benzopyrano [6,7,8-ij] -quinolizine-11-one The photosensitive resin composition, characterized in that at least one selected from. The photosensitive resin composition of claim 15, wherein the 3) photopolymerization initiator comprises 0.1 to 5 parts by weight based on 100 parts by weight of the photosensitive resin composition. The method according to claim 15, wherein the solvent 4) methyl ethyl ketone, methyl cellosolve, ethyl cellosolve, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol dimethyl ether, propylene glycol diethyl ether, diethylene glycol dimethyl Ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, 2-ethoxy propanol, 2-methoxy propanol, 3-methoxy butanol, cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate, propylene At least one member selected from the group consisting of glycol ethyl ether acetate, 3-methoxybutyl acetate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate and dipropylene glycol monomethyl ether Photosensitive resin composition to be. The photosensitive resin composition of claim 15, wherein the solvent 4) comprises 10 to 95 parts by weight based on 100 parts by weight of the photosensitive resin composition. The photosensitive resin composition according to claim 15, wherein the photosensitive resin composition further comprises a colorant. The photosensitive resin composition of claim 23, wherein the colorant comprises 0.5 to 20 parts by weight based on 100 parts by weight of the photosensitive resin composition. The photosensitive resin composition of claim 15, wherein the photosensitive resin composition comprises at least one additive selected from the group consisting of alkali-soluble acrylic copolymer resins, photosensitizers, curing accelerators, thermal polymerization inhibitors, plasticizers, adhesion promoters, fillers, and surfactants. The photosensitive resin composition characterized by the above-mentioned. The photosensitive resin composition of claim 25, wherein the additive comprises 0.01 to 10 parts by weight based on 100 parts by weight of the photosensitive resin composition. Hardened | cured material formed from the photosensitive resin composition of Claim 15.

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