TWI461478B - Photo-sensitivity resin composition, overcoating layer of color filter and photo-sensitivity resin adhesive - Google Patents

Photo-sensitivity resin composition, overcoating layer of color filter and photo-sensitivity resin adhesive Download PDF

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TWI461478B
TWI461478B TW099102094A TW99102094A TWI461478B TW I461478 B TWI461478 B TW I461478B TW 099102094 A TW099102094 A TW 099102094A TW 99102094 A TW99102094 A TW 99102094A TW I461478 B TWI461478 B TW I461478B
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alkali
weight
resin binder
parts
soluble resin
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TW201125917A (en
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Shean Jeng Jong
Yu Tsai Hsieh
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Daxin Materials Corp
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Description

感光性樹脂組成物、彩色濾光片的保護膜與感光樹脂 膠合劑 Photosensitive resin composition, protective film for color filter, and photosensitive resin Glue

本發明是有關於一種感光性樹脂組成物、彩色濾光片的保護膜與感光樹脂膠合劑,且特別是有關於一種具有較高的透光度、耐熱性、耐酸性、耐鹼性與耐熱變色性等特性的感光性樹脂組成物、彩色濾光片的保護膜與感光樹脂膠合劑。 The invention relates to a photosensitive resin composition, a protective film of a color filter and a photosensitive resin adhesive, and particularly relates to a light transmittance, heat resistance, acid resistance, alkali resistance and heat resistance. A photosensitive resin composition having characteristics such as discoloration, a protective film of a color filter, and a photosensitive resin binder.

一般來說,液晶顯示器面板的彩色濾光片的製作方法是先在玻璃基板上形成多個黑色矩陣(black matrix),然後再於相鄰的黑色矩陣之間依序形成紅、綠、藍的顏色層來作為畫素(pixel),使得當光線通過畫素時即會顯現出顏色。 Generally, a color filter of a liquid crystal display panel is formed by forming a plurality of black matrices on a glass substrate, and then sequentially forming red, green, and blue colors between adjacent black matrices. The color layer acts as a pixel, so that when the light passes through the pixel, it will appear.

此外,在彩色濾光片製作完成後,接著會形成透明電極來覆蓋黑色矩陣與顏色層。通常,在彩色濾光片和透明電極之間還會形成一層保護膜(overcoating layer),使彩色濾光片的表面較為平坦,以助於透明電極的製造,且亦可保護彩色濾光片不受後續製程的影響。一般而言,上述的保護膜必須具備有高的透光度、附著性、耐熱性、耐酸性與耐鹼性。 In addition, after the color filter is completed, a transparent electrode is then formed to cover the black matrix and the color layer. Generally, an overcoating layer is formed between the color filter and the transparent electrode to make the surface of the color filter flat, to facilitate the manufacture of the transparent electrode, and to protect the color filter. Affected by subsequent processes. In general, the above protective film must have high light transmittance, adhesion, heat resistance, acid resistance and alkali resistance.

在一些文獻中,提出了有關彩色濾光片的保護膜的相關技術,例如US 6582862、US 7097959、WO 2006/129924等專利。在上述文獻中,揭露了彩色濾光片的保護膜為負型光阻組成物(negative resist composition),其包括鹼可溶 性樹脂膠合劑(alkali dissolvable resin binder)、光聚合型化合物(photopolymerization compound)、光起始劑(photopolymerization initiator)與溶劑。然而,這些文獻中所提出的組成物的耐鹼性、耐酸性、耐熱變色性等特性皆較差。 In some documents, related art relating to a protective film for a color filter has been proposed, such as US 6,582,862, US Pat. No. 7,097,759, WO 2006/129924, and the like. In the above documents, it is disclosed that the protective film of the color filter is a negative resist composition including alkali soluble. Alkali dissolvable resin binder, photopolymerization compound, photopolymerization initiator and solvent. However, the compositions proposed in these documents are inferior in properties such as alkali resistance, acid resistance, and heat discoloration resistance.

因此,用於彩色濾光片的保護膜的組成物的研發及其特性的提昇已成為業界發展的重要課題之一。 Therefore, the development of the composition of the protective film for a color filter and the improvement of its characteristics have become one of the important topics in the development of the industry.

本發明提供一種感光性樹脂組成物,其具有較高的透光度、耐熱性、耐酸性、耐鹼性與耐熱變色性等特性。 The present invention provides a photosensitive resin composition which has characteristics such as high light transmittance, heat resistance, acid resistance, alkali resistance, and heat discoloration resistance.

本發明另提供一種彩色濾光片的保護膜,其可有效地保護彩色濾光片。 The present invention further provides a protective film for a color filter which can effectively protect a color filter.

本發明提供一種與感光樹脂膠合劑,其具有較高的透光度、耐熱性、耐酸性、耐鹼性與耐熱變色性等特性。 The present invention provides a photosensitive resin adhesive which has characteristics of high light transmittance, heat resistance, acid resistance, alkali resistance and heat discoloration resistance.

本發明提出一種感光性樹脂組成物,其包括(A)鹼可溶性樹脂膠合劑、(B)光聚合型含乙烯性不飽和基的化合物、(C)光起始劑、(D)有機酸酐、(E)分子中至少含有2個環氧基的化合物以及(F)有機溶劑。(A)鹼可溶性樹脂膠合劑含有由結構式(1)所表示的聚合物, 其中x=1~10莫耳百分比;y=29~59莫耳百分比;a+b=40~60莫耳百分比;a=15~40莫耳百分比;b=5~30莫耳百分比;R為苯甲基、苯基、CN或C(O)OR2,其中R2為C1~C15的直鏈或環狀烷基、苯基、苯甲基或烯丙基;R1為H或C1~C4的烷基。 The present invention provides a photosensitive resin composition comprising (A) an alkali-soluble resin binder, (B) a photopolymerizable ethylenically unsaturated group-containing compound, (C) a photoinitiator, (D) an organic acid anhydride, (E) a compound having at least two epoxy groups in the molecule and (F) an organic solvent. (A) the alkali-soluble resin binder contains the polymer represented by the structural formula (1), Wherein x=1~10 mole percentage; y=29~59 mole percentage; a+b=40~60 mole percentage; a=15~40 mole percentage; b=5~30 mole percentage; R is Benzyl, phenyl, CN or C(O)OR2, wherein R2 is a C1 to C15 linear or cyclic alkyl group, a phenyl group, a benzyl group or an allyl group; and R 1 is H or a C1 to C4 group. alkyl.

依照本發明實施例所述之感光性樹脂組成物,上述之(A)鹼可溶性樹脂膠合劑的重量平均分子量例如介於3000~300000之間。 According to the photosensitive resin composition of the embodiment of the invention, the weight average molecular weight of the above (A) alkali-soluble resin binder is, for example, between 3,000 and 300,000.

依照本發明實施例所述之感光性樹脂組成物,上述之(A)鹼可溶性樹脂膠合劑的固含量例如介於10~50%之間。 According to the photosensitive resin composition of the embodiment of the invention, the solid content of the above (A) alkali-soluble resin binder is, for example, between 10 and 50%.

依照本發明實施例所述之感光性樹脂組成物,上述之(A)鹼可溶性樹脂膠合劑的酸價例如介於10~400mgKOH/g之間。 According to the photosensitive resin composition of the embodiment of the invention, the acid value of the (A) alkali-soluble resin binder is, for example, between 10 and 400 mgKOH/g.

依照本發明實施例所述之感光性樹脂組成物,基於(A)鹼可溶性樹脂膠合劑為100重量份,(B)光聚合型含乙烯性不飽和基的化合物的含量例如介於1~250重量份之間。 The photosensitive resin composition according to the embodiment of the invention is based on 100 parts by weight of the (A) alkali-soluble resin binder, and the content of the (B) photopolymerizable ethylenically unsaturated group-containing compound is, for example, from 1 to 250. Between parts by weight.

依照本發明實施例所述之感光性樹脂組成物,基於(A)鹼可溶性樹脂膠合劑為100重量份,(C)光起始劑的含量例如介於0.1~100重量份之間。 The photosensitive resin composition according to the embodiment of the present invention is contained in an amount of, for example, 100 parts by weight based on (A) the alkali-soluble resin binder, and (C) the photoinitiator is, for example, between 0.1 and 100 parts by weight.

依照本發明實施例所述之感光性樹脂組成物,基於(A)鹼可溶性樹脂膠合劑為100重量份,(D)有機酸酐的含量例如介於0.1~100重量份之間。 The photosensitive resin composition according to the embodiment of the present invention has a content of (D) an organic acid anhydride of, for example, 0.1 to 100 parts by weight based on 100 parts by weight of the (A) alkali-soluble resin binder.

依照本發明實施例所述之感光性樹脂組成物,基於(A)鹼可溶性樹脂膠合劑為100重量份,(E)分子中至少含有2個環氧基的化合物的含量例如介於0.1~100重量份之間。 The photosensitive resin composition according to the embodiment of the present invention has a content of at least two epoxy groups in the molecule (E), for example, between 0.1 and 100, based on 100 parts by weight of the (A) alkali-soluble resin binder. Between parts by weight.

依照本發明實施例所述之感光性樹脂組成物,基於(A)鹼可溶性樹脂膠合劑為100重量份,(F)有機溶劑的含量例如介於10~2500重量份之間。 The photosensitive resin composition according to the embodiment of the present invention has a content of (F) an organic solvent of, for example, 10 to 2500 parts by weight based on 100 parts by weight of the (A) alkali-soluble resin binder.

依照本發明實施例所述之感光性樹脂組成物,上述之感光性樹脂組成物的黏度例如介於1~200cps之間。 According to the photosensitive resin composition of the embodiment of the invention, the photosensitive resin composition has a viscosity of, for example, between 1 and 200 cps.

本發明另提出一種彩色濾光片的保護膜,其是由上述之感光性樹脂組成物聚合而成。 The present invention further provides a protective film for a color filter which is obtained by polymerizing the above-mentioned photosensitive resin composition.

本發明再提出一種感光樹脂膠合劑,其包括上述的(A)鹼可溶性樹脂膠合劑。 The present invention further proposes a photosensitive resin binder comprising the above (A) alkali-soluble resin binder.

基於上述,由於本發明之感光性樹脂組成物具有較高的透光度、耐熱性、耐酸性、耐鹼性與耐熱變色性等特性,因此由本發明之感光性樹脂組成物聚合而成的彩色濾光片 的保護膜可以有效地保護彩色濾光片,以進一步提升元件效能。 In view of the above, since the photosensitive resin composition of the present invention has characteristics such as high light transmittance, heat resistance, acid resistance, alkali resistance, and heat discoloration resistance, the color of the photosensitive resin composition of the present invention is polymerized. Filter The protective film effectively protects the color filter to further enhance component performance.

為讓本發明之上述特徵和優點能更明顯易懂,下文特舉實施例,並配合所附圖式作詳細說明如下。 The above described features and advantages of the present invention will be more apparent from the following description.

本發明提出了一種感光性樹脂組成物,其具有較高的透光度、耐熱性、耐酸性、耐鹼性與耐熱變色性等特性,因此使得由此感光性樹脂組成物聚合而成的彩色濾光片的保護膜可以有效地保護彩色濾光片。 The present invention proposes a photosensitive resin composition which has high light transmittance, heat resistance, acid resistance, alkali resistance and heat discoloration resistance, and thus colors obtained by polymerizing the photosensitive resin composition The protective film of the filter can effectively protect the color filter.

本發明另提出一種感光樹脂膠合劑,其包括下列的(A)鹼可溶性樹脂膠合劑。 The present invention further provides a photosensitive resin binder comprising the following (A) alkali-soluble resin binder.

本發明之感光性樹脂組成物包括(A)鹼可溶性樹脂膠合劑、(B)光聚合型含乙烯性不飽和基的化合物、(C)光起始劑、(D)有機酸酐、(E)分子中至少含有2個環氧基的化合物以及(F)有機溶劑。此外,不論在膠合劑中或光阻調配時較佳皆使用對生物安全性高的丙二醇甲醚醋酸酯(propylene glycol methyl ether acetate,PGMEA)、3-甲氧基乙酸丁酯(3-methoxy butyl acetate,MBA)、3-乙氧基丙酸乙酯(3-ethoxy ethyl propionate,EEPA)等溶劑。 The photosensitive resin composition of the present invention comprises (A) an alkali-soluble resin binder, (B) a photopolymerizable ethylenically unsaturated group-containing compound, (C) a photoinitiator, (D) an organic acid anhydride, (E) A compound having at least two epoxy groups in the molecule and (F) an organic solvent. In addition, it is preferred to use propylene glycol methyl ether acetate (PGMEA) or 3-methoxy butyl methacrylate in the adhesive or in the photoresist formulation. Acetate, MBA), 3-ethoxy ethyl propionate (EEPA) and other solvents.

(A)鹼可溶性樹脂膠合劑: (A) Alkali-soluble resin binder:

(A)鹼可溶性樹脂膠合劑是由結構式(1)所表示的聚合物與PGMEA、MBA、EEPA等溶劑所組成之溶液, 其中x=1~10莫耳百分比;y=29~59莫耳百分比;a+b=40~60莫耳百分比;a=15~40莫耳百分比;b=5~30莫耳百分比;R為苯甲基、苯基、CN或C(O)OR2,其中R2為C1~C15的直鏈或環狀烷基、苯基、苯甲基或烯丙基;R1為H或C1~C4的烷基。(A)鹼可溶性樹脂膠合劑的重量平均分子量例如介於3000~300000之間;固含量例如介於10~50%之間;酸價例如介於10~400mgKOH/g之間。 (A) the alkali-soluble resin binder is a solution composed of a polymer represented by the structural formula (1) and a solvent such as PGMEA, MBA, or EEPA. Wherein x=1~10 mole percentage; y=29~59 mole percentage; a+b=40~60 mole percentage; a=15~40 mole percentage; b=5~30 mole percentage; R is Benzyl, phenyl, CN or C(O)OR2, wherein R2 is a C1 to C15 linear or cyclic alkyl group, a phenyl group, a benzyl group or an allyl group; and R 1 is H or a C1 to C4 group. alkyl. The weight average molecular weight of the (A) alkali-soluble resin binder is, for example, between 3,000 and 300,000; the solid content is, for example, between 10 and 50%; and the acid value is, for example, between 10 and 400 mgKOH/g.

(B)光聚合型含乙烯性不飽和基的化合物 (B) Photopolymerizable ethylenically unsaturated group-containing compound

基於(A)鹼可溶性樹脂膠合劑為100重量份,(B)光聚合型含乙烯性不飽和基的化合物的含量例如介於1~250重量份之間,較佳是介於20~60重量份之間。 The content of the (B) photopolymerizable ethylenically unsaturated group-containing compound is, for example, between 1 and 250 parts by weight, preferably between 20 and 60 parts by weight, based on 100 parts by weight of the (A) alkali-soluble resin binder. Between the shares.

(B)光聚合型含乙烯性不飽和基的化合物為具有至少一個乙烯性不飽和基的乙烯性不飽和化合物。(B)光聚合型含乙烯性不飽和基的化合物例如是乙二醇二甲基丙烯酸酯(ethylene glycol di(meth)acrylate)、具有2-14個環氧乙烷基(ethyleneoxide group)的聚乙二醇二甲基丙烯酸酯(polyethylene glycol di(meth)acrylate)、三甲醇丙烷二甲基丙烯酸酯(trimethylol propane di(meth)acrylate)、三甲醇丙烷三甲基丙烯酸酯(trimethylol propane tri(meth)acrylate)、異戊四醇三甲基丙烯酸酯(pentaerythritol tri(meth)acrylate)、異戊四醇四甲基丙烯酸酯(pentaerythritol tetra(meth)acrylate)、具有2-14個環氧丙烷基(propyleneoxide group)的丙烯甘醇二甲基丙烯酸酯(propyleneglycol di(meth)acrylate)、二季戊四醇五甲基丙烯酸酯(dipentaerythritol penta(meth)acrylate)、二季戊四醇六甲基丙烯酸酯(dipentaerythritol hexa(meth)acrylate,DPHA)、三羥甲基丙烷三縮水甘油醚丙烯酸添加劑(trimethylolpropanetriglycidylether acrylic acid additives)、雙酚A二縮水甘油醚丙烯酸添加劑(bisphenol A diglycidylether acrylic acid additives)、鄰苯二甲酸二酯類的(甲基)丙烯酸-β-羥乙酯(phthalate diesters of β-hydroxyethyl(meth)acrylate)、甲苯二異氫酸酯添加劑的(甲基)丙烯酸-β-羥乙酯(toluene diisocyanate additives of β-hydroxyethyl(meth)acrylate)或具有乙烯性不飽和鍵(ethylenically unsaturated bond)的聚合性化合物(polymeric compound),其中具有乙烯性不飽和鍵的聚合性化合物是選自由二三羥基甲基丙烷四丙烯酸酯(ditrimethylol propanetetraacrylate)、乙氧基化三聚異氫酸三丙烯酸酯(tris(2-acryloxyethyl)isocyanurate)、含乙氧基季戊五醇四丙烯酸酯(ethoxylated pentaerylthritoltetraacrylate)(EO 4mol)、季戊五醇四丙烯酸酯(pentaerythritoltetraacrylate)(EO 35mol)、含乙氧基三羥甲基丙烷三丙烯酸酯(ethoxylated trimethylolpropanetriacrylate)(EO 9mol)、含乙氧基三羥甲基丙烷三丙烯酸酯(EO 3mol)、含丙氧基三羥甲基丙烷三丙烯酸酯(propxylated pentaerythritoltetraacrylate)(PO 4mol)、九乙二醇二丙烯酸酯(nonaethylene glycol diacrylate)、以己內酯改質的雙季戊四醇六丙烯酸酯(dipentaerythritolhexaacrylate-modified caprolactone)和三羥甲基丙烷丙氧基三丙烯酸酯(trimethylolpropanepropoxylate triacrylate)所組成之群組,其中較佳為二季戊四醇六甲基丙烯酸酯。 (B) The photopolymerizable ethylenically unsaturated group-containing compound is an ethylenically unsaturated compound having at least one ethylenically unsaturated group. (B) The photopolymerizable ethylenically unsaturated group-containing compound is, for example, ethylene glycol di(meth)acrylate, which has a polymerization of 2 to 14 ethylene oxide groups. Polyethylene glycol di(meth)acrylate, trimethylol propane di(meth)acrylate, trimethylol propane tri(meth) Acetate), pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, having 2-14 propylene oxide groups ( Propyleneoxide group) propyleneglycol di(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth) Acrylate, DPHA), trimethylolpropanetriglycidylether acrylic acid additive, bisphenol A diglycidyl ether acrylic acid additive phenol A diglycidylether acrylic acid additives), phthalate esters of (meth) acrylic acid - β - hydroxyethyl methacrylate (phthalate diesters of β -hydroxyethyl (meth ) acrylate), tolylene hydrogen ester additive (A yl) acrylic acid - β - hydroxyethyl methacrylate (toluene diisocyanate additives of β -hydroxyethyl ( meth) acrylate) or a compound having a polymerizable (polymeric compound) ethylenically unsaturated bond (ethylenically unsaturated bond), wherein having an ethylenically unsaturated bond The polymerizable compound is selected from the group consisting of ditrimethylol propanetetraacrylate, tris(2-acryloxyethyl)isocyanurate, and ethoxylated pentaerythritol Ethoxylated pentaerylthritoltetraacrylate (EO 4mol), pentaerythritoltetraacrylate (EO 35mol), ethoxylated trimethylolpropanetriacrylate (EO 9mol), Ethoxytrimethylolpropane triacrylate (EO 3mol), propoxytrimethylolpropane triacrylate (propx Citricated pentaerythritoltetraacrylate) (PO 4 mol), nonaethylene glycol diacrylate, dipentaerythritol hexaacrylate-modified caprolactone and trimethylolpropane propoxy triacrylate A group consisting of trimethylolpropanepropoxylate triacrylate, preferably dipentaerythritol hexamethacrylate.

(C)光起始劑: (C) Photoinitiator:

基於(A)鹼可溶性樹脂膠合劑為100重量份,(C)光起始劑的含量例如介於0.1~100重量份之間,較佳是介於0.5~10重量份之間。 The content of the (C) photoinitiator is, for example, between 0.1 and 100 parts by weight, preferably between 0.5 and 10 parts by weight, based on 100 parts by weight of the (A) alkali-soluble resin binder.

(C)光起始劑例如為氧化膦(phosphine oxide)系化合物、羰基(carbonyl)系化合物、胺羰(aminocarbonyl)系化合物、三嗪(triazine)系化合物或肟(oxime)系化合物,且可與 共光起始劑(co-photoinitiator)搭配使用。共光起始劑例如為胺(amine)系化合物、烷氧基駢蒽(alkoxyantharcene)系化合物或噻噸(thioxanthone)系化合物。 (C) The photoinitiator is, for example, a phosphine oxide compound, a carbonyl compound, an aminocarbonyl compound, a triazine compound or an oxime compound, and versus A co-photoinitiator is used together. The co-photogenic initiator is, for example, an amine compound, an alkoxyantharcene compound or a thioxanthone compound.

氧化膦系化合物例如是芳膦氧化物(arylphosphine oxide)、醯膦(acylphosphine oxide)、雙醯膦(bisacylphosphine oxide)、2,4,6-三甲基苯甲醯基-二苯基氧膦(2,4,6-trimethylbenzoyldiphenylphosphine oxide,TPO)、2,6-二乙基苯甲醯基-二苯基氧膦(2,6-diethylbenzoyldiphenylphosphine oxide)、2,6-二甲基苯甲醯基-二苯基氧膦(2,6-dimethoxybenzoyldiphenylphosphine oxide)、2,6-二氯苯甲醯基-二苯基氧膦(2,6-dichlorobenzoyldiphenylphosphine oxide)、2,3,5,6-四甲基苯甲醯基-二苯基氧膦(2,3,5,6-tetramethylbenzoyldiphenylphosphine oxide)、苯甲醯二(2,6-二甲苯基)膦酸(benzoyldi(2,6-dimethylphenyl)phosphonate)、2,4,6-三甲基苯甲醯基苯基膦酸乙酯(2,4,6-trimethylbenzoylethoxyphenylphosphine oxide)、雙(2,4,6-三甲基苯甲醯基)苯基氧化膦)(bis(2,4,6-trimethylbenzoyl)phenylphosphine(I-819))或雙(2,6-甲氧苯甲醯基)-2,4,4-三甲基苯基氧膦(bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentylphosphine oxide))。 The phosphine oxide-based compound is, for example, an arylphosphine oxide, an acylphosphine oxide, a bisacylphosphine oxide, 2,4,6-trimethylbenzimidyl-diphenylphosphine oxide ( 2,6,6-trimethylbenzoyldiphenylphosphine oxide, TPO), 2,6-diethylbenzoyldiphenylphosphine oxide, 2,6-dimethylbenzylidene 2,6-dimethoxybenzoyldiphenylphosphine oxide, 2,6-dichlorobenzoyldiphenylphosphine oxide, 2,3,5,6-tetramethyl Benzoyldi(2,6-dimethylphenyl)phosphonate, 2,3,5,6-tetramethylbenzoyldiphenylphosphine oxide 2,4,6-trimethylbenzoylethoxyphenylphosphine oxide, bis(2,4,6-trimethylbenzylidene)phenylphosphine oxide (bis(2,4,6-trimethylbenzoyl)phenylphosphine(I-819)) or bis(2,6-methoxybenzhydryl)-2,4,4-trimethylphenylphosphine oxide (bis) 2,6-dimethoxybenzoyl)-2,4,4-trimethylpentylphosphine oxide)).

羰基系化合物、胺羰系化合物、三嗪(triazine)系化合 物、肟系化合物等系列化合物例如是乙醯苯(acetophenone)、二苯甲酮(benzophenone)、二苯基酮(biphenylketone)、1-羥基-1-環己基苯基甲酮(1-hydroxy-1-benzoylcyclohexane(I-184))、芐基丙酮2,2-二甲氧基-1,2-二苯乙烷-1-酮(benzyldimethylketal 2,2-dimethoxy-1,2-diphenylethane-1-one(I-651))、1-芐基-1-二甲基叔胺-1-(4-嗎啉-苯甲醯)丙烷(1-benzyl-1-dimethylamino-1-(4-morpholino-benzoyl)propane(I-369))、2-嗎啉-2-(4-甲硫基)苯甲醯丙烷(2-morpholyl-2-(4-methylmercapto)benzoylpropane(I-907))、乙基蒽醌(ethylanthraquinone)、4-苯甲醯基-4-甲基二苯硫醚(4-benzoyl-4-methyldiphenylsulfide)、苯甲醯苯甲醇丁醚(benzoinbutylether)、2-羥基-2-苯甲醯丙烷(2-hydroxy-2-benzoylpropane)、2-羥基-2-(4-異丙基)苯甲醯丙烷(2-hydroxy-2-(4-isopropyl)benzoylpropane)、4-丁基苯甲醯三氯甲烷(4-butylbenzoyltrichloromethane)、4-苯氧基苯甲醯二氯甲烷(4-phenoxybenzoyldichloromethane)、苯甲醯甲酸甲酯(benzoylmethylformate)、1,7-雙(9-吖啶基)庚烷(1,7-bis(9-acridinyl)heptane)、9-n-丁基-3,6-雙(2-嗎啉-異丁醯)咔唑(9-n-butyl-3,6-bis(2-morpholino-isobutyloyl)carbazole)、10-丁基-2-chloroacrydone(10-butyl-2-chloroacrydone)、2-[2-(4-甲氧基-苯基)-乙烯基]-4,6-雙-三氯甲基-[1,3,5]三嗪(2-[2-(4-methoxy-phenyl)-vinyl]-4,6-bis-trichloromethyl-[1,3,5]triazine)、2-(4-甲氧基-萘-1-基)-4,6-雙-三氯甲基-[1,3,5]三嗪 (2-(4-methoxy-naphthalen-1-yl)-4,6-bis-trichloromethyl-[1,3,5]triazine)、2-甲苯[1,3]二氧雜環戊烯-5-基-4,6-雙-三氯甲基-[1,3,5]三嗪(2-benzo[1,3]dioxol-5-yl-4,6-bis-trichloromethyl-[1,3,5]triazine)、2-甲基-4,6-雙(三氯甲基)-s-三嗪(2-methyl-4,6-bis(trichloromethyl)-s-triazine)、2-苯基-4,6-雙(三氯甲基)-s-三嗪(2-phenyl-4,6-bis(trichloromethyl)-s-triazine)或2-萘酯-4,6-雙(三氯甲基)-s-三嗪(2-naphthyl-4,6-bis(trichloromethyl)-s-triazine)。 Carbonyl compound, amine carbonyl compound, triazine compound A series of compounds such as lanthanide compounds, such as acetophenone, benzophenone, biphenylketone, 1-hydroxy-1-cyclohexyl phenyl ketone (1-hydroxy-) 1-benzoylcyclohexane (I-184)), benzyl acetone 2,2-dimethoxy-1,2-diphenylethane-1-one (benzyldimethylketal 2,2-dimethoxy-1,2-diphenylethane-1- One(I-651)), 1-benzyl-1-dimethyl-tert-amine-1-(4-morpholin-benzamide)propane (1-benzyl-1-dimethylamino-1-(4-morpholino- Benzoyl)propane (I-369)), 2-morpholyl-2-(4-methylmercapto)benzoylpropane (I-907), ethyl An (ethylanthraquinone), 4-benzoyl-4-methyldiphenylsulfide, benzoinbutylether, 2-hydroxy-2-phenyl 2-hydroxy-2-benzoylpropane, 2-hydroxy-2-(4-isopropyl)benzoylpropane, 4-butyl benzoyl 4-butylbenzoyltrichloromethane, 4-phenoxybenzoyldichloromethane, methyl benzhydrazide Zoylmethylformate), 1,7-bis(9-acridinyl)heptane, 9-n-butyl-3,6-bis(2-morpholine-iso Butyr) 9-n-butyl-3,6-bis(2-morpholino-isobutyloyl)carbazole, 10-butyl-2-chloroacrydone (10-butyl-2-chloroacrydone), 2-[2- (4-methoxy-phenyl)-vinyl]-4,6-bis-trichloromethyl-[1,3,5]triazine (2-[2-(4-methoxy-phenyl)-vinyl ]-4,6-bis-trichloromethyl-[1,3,5]triazine), 2-(4-methoxy-naphthalen-1-yl)-4,6-bis-trichloromethyl-[1, 3,5]triazine (2-(4-methoxy-naphthalen-1-yl)-4,6-bis-trichloromethyl-[1,3,5]triazine), 2-toluene[1,3]dioxol-5- 4-,6-bis-trichloromethyl-[1,3,5]triazine (2-benzo[1,3]dioxol-5-yl-4,6-bis-trichloromethyl-[1,3, 5]triazine), 2-methyl-4,6-bis(trichloromethyl)-s-triazine (2-methyl-4,6-bis(trichloromethyl)-s-triazine), 2-phenyl- 4,6-bis(trichloromethyl)-s-triazine (2-phenyl-4,6-bis(trichloromethyl)-s-triazine) or 2-naphthyl ester-4,6-bis(trichloromethyl) )-s-triazine (2-naphthyl-4,6-bis(trichloromethyl)-s-triazine).

胺系化合物例如是三乙醇胺(triethanolamine)、甲基二乙醇胺(methyldiethanolamine)、三異丙醇胺(triisopropylamine)、4-二甲基胺基甲基苯甲酸乙酯(4-dimethylaminomethyl benzoate)、4-二甲基胺基乙基苯甲酸乙酯(4-dimethylaminoethyl benzoate)、4-二甲基胺基異戊基苯甲酸乙酯(4-methylaminoisoamyl benzoate)、2-甲基胺基乙基苯甲酸乙酯(2-methylaminoethyl benzoate)、4-二甲基胺基-2-乙基已基苯甲酸乙酯(4-dimethylamino-2-ethylhexyl benzoate)、N,N-甲基對甲苯胺(N,N-methylparatoluidine)、4,4’-雙(二甲基胺基)二苯甲酮(4,4’-bis(dimethylamino)benzophenone)、4,4’-雙(二乙基胺基)二苯甲酮(4,4’-bis(diethylamino)benzophenone)或4,4’-雙(乙基甲基胺基)二苯甲酮(4,4’-bis(ethylmethylamino)benzophenone)。 The amine compound is, for example, triethanolamine, methyldiethanolamine, triisopropylamine, 4-dimethylaminomethyl benzoate, 4- 4-dimethylaminoethyl benzoate, 4-methylaminoisoamyl benzoate, 2-methylaminoethyl benzoate 2-methylaminoethyl benzoate, 4-dimethylamino-2-ethylhexyl benzoate, N,N-methyl-p-toluidine (N, N -methylparatoluidine), 4,4'-bis(dimethylamino)benzophenone, 4,4'-bis(diethylamino)benzophenone Ketone (4,4'-bis(diethylamino)benzophenone) or 4,4'-bis(ethylmethylamino)benzophenone.

烷氧基駢蒽系化合物例如是9,10-二甲氧基蒽(9,10-dimethoxyanthracene)、9,10-二乙氧基蒽(9,10-diethoxyanthracene)、2-乙基9,10-二甲氧基蒽 (2-ethyl-9,10-dimethoxyanthracene)或2-乙基9,10-二乙氧基蒽(2-ethyl-9,10-diethoxyanthracene)。 The alkoxy ruthenium compound is, for example, 9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl 9,10 -dimethoxy oxime (2-ethyl-9,10-dimethoxyanthracene) or 2-ethyl 9,10-diethoxyanthracene.

噻噸系化合物例如是2-異丙基噻噸酮(2-isopropylthioxanthone)、4-異丙基噻噸酮(4-isopropylthioxanthone,IPTX)、2,4-二乙基噻噸酮(2,4-diethylthioxanthone,DETX)、2,4-三氯基噻噸酮(2,4-trichlorothioxanthone)或1-氯-4-丙基噻噸酮(1-chloro-4-propoxythioxanthone)。 The thioxantane compounds are, for example, 2-isopropylthioxanthone, 4-isopropylthioxanthone (IPTX), 2,4-diethylthioxanthone (2,4). -diethylthioxanthone, DETX), 2,4-trichlorothioxanthone or 1-chloro-4-propoxythioxanthone.

(D)有機酸酐: (D) Organic acid anhydride:

基於(A)鹼可溶性樹脂膠合劑為100重量份,(D)有機酸酐的含量例如介於0.1~100重量份之間,較佳介於2~5重量份之間。 The content of the (D) organic acid anhydride is, for example, between 0.1 and 100 parts by weight, preferably between 2 and 5 parts by weight, based on 100 parts by weight of the (A) alkali-soluble resin binder.

(D)有機酸酐例如為順丁烯二酸酐(maleic anhydride,MA)、伊康酸酐(itaconic anhydride)、四氫酞酐(tetrahydrophthalic anhydride)、檸康酸酐(citraconic anhydride)或中康酸酐(mesaconic anhydride),其中較佳為順丁烯二酸酐。上述之有機酸酐可單獨或混合數種使用。 (D) The organic acid anhydride is, for example, maleic anhydride (MA), itaconic anhydride, tetrahydrophthalic anhydride, citraconic anhydride or mesaconic anhydride. Wherein maleic anhydride is preferred. The above organic acid anhydrides may be used singly or in combination of several kinds.

(E)分子中至少含有2個環氧基的化合物: (E) a compound having at least two epoxy groups in the molecule:

基於(A)鹼可溶性樹脂膠合劑為100重量份,(E)分子中至少含有2個環氧基的化合物的含量例如介於0.1~100重量份之間,較佳為介於2~10重量份之間。 The content of the compound having at least two epoxy groups in the (E) molecule is, for example, between 0.1 and 100 parts by weight, preferably between 2 and 10 parts by weight, based on 100 parts by weight of the (A) alkali-soluble resin binder. Between the shares.

(E)分子中至少含有2個環氧基的化合物例如是雙酚A 環氧樹脂(bisphenol A type epoxy)化合物、雙酚S環氧樹脂(bisphenol S type epoxy)化合物、芴-9-雙酚二環氧甘油醚(fluorene-9-bisphenol diglycidyl Ether,FBDE)、雙酚A型環氧樹脂(bisphenol A type epoxy resin)(例如:油化Shell Epoxy公司製,商品名為Epikote 828、1001、1002、1004等)、雙酚A型環氧樹脂之醇型羥基(alcoholic hydroxyl)與環氧氯丙烷(epichlorohydrin)反應而得之環氧樹脂(例如:日本化藥公司製,商品名為NER-1302,環氧當量323,軟化點76℃)、雙酚F型環氧樹脂(bisphenol F type epoxy resin)(例如:油化Shell Epoxy公司製,商品名為Epikote 807、4001、4002、4004等)、雙酚F型環氧樹脂之醇型羥基(alcoholic hydroxyl)與環氧氯丙烷(epichlorohydrin)反應而得之環氧樹脂(例如:日本化藥公司製,商品名為NER-7406,環氧當量350,軟化點66℃)、二苯基縮水甘油醚(biphenyl glycidyl ether)(例如:油化Shell Epoxy公司製,商品名為Epikote YX4000)、(苯)酚醛型環氧樹脂(phenol novolac type epoxy resin)(例如:日本化藥公司製,商品名為EPPN-201;油化Shell Epoxy公司製,商品名為Epikote 152、154、157S65、157S70;陶氏化學公司製,商品名為DEN-438)、甲(苯)酚醛型環氧樹脂(cresol novolac type epoxy resin)(例如:日本化藥公司製,商品名為EOCN-102S、1020、104S)、三縮水甘油異氰尿酸酯(triglycidyl isocyanurate)(例如:日產化學公司製,商品名為TEPIC)、三酚甲烷型環氧樹脂(trisphenol methane type epoxy resin)(例如:日本化藥公司製,商品名為EPPN-501、502、503)、芴型環氧樹脂(fluorene type epoxy resin)(例如:新日鐵化學公司製,商品名為ESF-300)、脂環式環氧樹脂(例如:Daicel化學工業公司製,商品名為Celloxide 2021P、EHPE)或環氧化聚丁二烯樹脂(epoxidized polybutadiene)(例如:Daicel化學工業公司製,商品名為Epolead PB3600),其中較佳為芴-9-雙酚二環氧甘油醚。上述之分子中至少含有2個環氧基之化合物可單獨使用或混合數種使用。 (E) a compound having at least two epoxy groups in the molecule, for example, bisphenol A Bisphenol A type epoxy compound, bisphenol S type epoxy compound, fluorene-9-bisphenol diglycidyl Ether (FBDE), bisphenol Bisphenol A type epoxy resin (for example: oiled Shell Epoxy, trade name: Epikote 828, 1001, 1002, 1004, etc.), alcoholic hydroxyl group of bisphenol A epoxy resin (alcoholic hydroxyl) An epoxy resin obtained by reacting with epichlorohydrin (for example, manufactured by Nippon Kayaku Co., Ltd., trade name: NER-1302, epoxy equivalent 323, softening point 76 ° C), bisphenol F type epoxy resin (bisphenol F type epoxy resin) (for example, oiled by Shell Epoxy, trade name: Epikote 807, 4001, 4002, 4004, etc.), alcoholic hydroxyl of bisphenol F epoxy resin and epoxy chloride Epoxy resin obtained by reaction of epichlorohydrin (for example, manufactured by Nippon Kayaku Co., Ltd., trade name: NER-7406, epoxy equivalent 350, softening point 66 ° C), biphenyl glycidyl ether (biphenyl glycidyl ether) For example: oiled Shell Epoxy company, the product name is Epikote YX 4000), phenol novolac type epoxy resin (for example, manufactured by Nippon Kayaku Co., Ltd., trade name EPPN-201; manufactured by Oiled Shell Epoxy Co., Ltd. under the trade name Epikote 152, 154, 157S65 157S70; manufactured by The Dow Chemical Company, trade name DEN-438), cresol novolac type epoxy resin (for example, manufactured by Nippon Kayaku Co., Ltd., trade name EOCN-102S, 1020) , 104S), triglycidyl isocyanurate (for example: manufactured by Nissan Chemical Co., Ltd., trade name TEPIC), trisphenol methane type epoxy resin (for example: Nippon Kayaku) Company-made, trade name EPPN-501, 502, 503), fluorene type Epoxy resin) (for example, manufactured by Nippon Steel Chemical Co., Ltd. under the trade name ESF-300), alicyclic epoxy resin (for example, manufactured by Daicel Chemical Industry Co., Ltd. under the trade name Celloxide 2021P, EHPE) or epoxidized polybutane An epoxidized polybutadiene (for example, manufactured by Daicel Chemical Industry Co., Ltd. under the trade name of Epolead PB3600), preferably yttrium-9-bisphenol diglycidyl ether. The compound containing at least two epoxy groups in the above molecule may be used singly or in combination of several kinds.

(F)有機溶劑: (F) Organic solvents:

基於(A)鹼可溶性樹脂膠合劑為100重量份,(F)有機溶劑的含量例如介於10~2500重量份之間,較佳是介於80~250重量份之間。 The content of the (F) organic solvent is, for example, between 10 and 2,500 parts by weight, preferably between 80 and 250 parts by weight, based on 100 parts by weight of the (A) alkali-soluble resin binder.

(F)有機溶劑例如是PGMEA、MBA或EEPA。上述之有機溶劑可單獨或混合數種使用。 (F) The organic solvent is, for example, PGMEA, MBA or EEPA. The above organic solvents may be used singly or in combination of several kinds.

此外,作為彩色濾光片的保護膜,本發明之感光性樹脂組成物主要是以(A)鹼可溶性樹脂膠合劑、(B)光聚合型含乙烯性不飽和基的化合物、(C)光起始劑、(D)有機酸酐、(E)分子中至少含有2個環氧基的化合物為主要成份。當然,視實際需求,必要時可加入以下的各種添加物。 Further, as a protective film for a color filter, the photosensitive resin composition of the present invention is mainly (A) an alkali-soluble resin binder, (B) a photopolymerizable ethylenically unsaturated group-containing compound, and (C) light. The initiator, (D) an organic acid anhydride, and a compound having at least two epoxy groups in the (E) molecule are main components. Of course, depending on the actual needs, the following additives can be added as necessary.

在一實施例中,可進一步加入密著助劑(coupling agent),以增進感光性樹脂組成物與彩色濾光片之間的附著度,以及增進感光性樹脂組成物與透明電極之間的附著度。基於感光性樹脂組成物為100重量份,密著助劑的使用 量可介於0.01~30重量份之間,較佳介於0.5~3重量份之間。密著助劑例如是含環氧基或含氨基的矽化合物,其例如為β-(3,4-環氧環己烷)乙基三甲氧基矽烷(β-(3,4-epoxycyclohexyl)ethyl trimethoxysilane)、β-(3,4-環氧環己烷)乙基三乙氧基矽烷(β-(3,4-epoxycyclohexyl)ethyl triethoxysilane)、γ-環氧丙烷三甲氧基矽烷(γ-glycidoxypropyl trimethoxysilane,GTS)、γ-環氧丙烷甲基二甲氧基矽烷(γ-glycidoxypropyl methyldimethoxysilane)、γ-環氧丙烷甲基二乙氧基矽烷(γ-glycidoxypropyl methyldiethoxysilane)、γ-環氧丙烷二甲氧基乙氧基矽烷(γ-glycidoxypropyl dimethoxy(ethoxy)silane)、γ-環氧丙烷二甲基甲氧基矽烷(γ-glycidoxypropyl dimethyl(methoxy)silane)、γ-環氧丙烷二甲基乙氧基矽烷(γ-glycidoxypropyl dimethyl(ethoxy)silane)、3,4-環氧丁基三甲氧基矽烷(3,4-epoxybutyltrimethoxysilane)、3,4-環氧丁基三乙氧基矽烷(3,4-epoxybutyltriethoxysilane)、N-(2-胺乙基)-3-胺丙基二甲氧基二甲基矽烷(N-(2-aminoethyl)-3-aminopropyldimethoxymethylsilane)、(3-胺丙基)三甲氧基矽烷((3-aminopropyl)trimethoxysilane)、(3-胺丙基三乙氧基矽烷((3-aminopropyl)triethoxysilane)、(N,N-二乙基-3-胺丙基)三甲氧基矽烷((N,N-diethyl-3-aminopropyl)trimethoxysilane)或N-β(胺乙基)γ-胺丙基三甲氧基矽烷)(N-β(aminoethyl)γ-aminopropyl trimethoxysilane)。上述之密著助劑可單獨使用或混合數種使 用。 In one embodiment, a adhesion agent may be further added to improve adhesion between the photosensitive resin composition and the color filter, and to improve adhesion between the photosensitive resin composition and the transparent electrode. degree. The adhesion aid may be used in an amount of from 0.01 to 30 parts by weight, preferably from 0.5 to 3 parts by weight, based on 100 parts by weight of the photosensitive resin composition. The adhesion promoter is, for example, an epoxy group-containing or amino group-containing hydrazine compound, which is, for example, β- (3,4-epoxycyclohexane)ethyltrimethoxydecane (β-(3,4-epoxycyclohexyl)ethyl). trimethoxysilane), β - (3,4- epoxycyclohexane) ethyl triethoxysilane Silane (β- (3,4-epoxycyclohexyl) ethyl triethoxysilane), γ- trimethoxy silane-oxide (γ-glycidoxypropyl Trimethoxysilane, GTS), γ-glycidoxypropyl methyldimethoxysilane, γ-glycidoxypropyl methyldiethoxysilane, γ-propylene oxide Γ-glycidoxypropyl dimethoxy(ethoxy)silane, γ-glycidoxypropyl dimethyl(methoxy)silane, γ-propylene oxide dimethyl ethoxylate Γ-glycidoxypropyl dimethyl(ethoxy)silane, 3,4-epoxybutyltrimethoxysilane, 3,4-epoxybutyltriethoxydecane (3,4) -epoxybutyltriethoxysilane), N-(2-Aminoethyl)-3-aminopropyldimethoxydimethylsilane (N-(2-aminoethyl)-3-aminopro Pyldimethoxymethylsilane), (3-aminopropyl)trimethoxysilane, (3-aminopropyltriethoxysilane), (N,N-diethyl) N-N-diethyl-3-aminopropyltrimethoxysilane or N-β(aminoethyl)γ-aminopropyltrimethoxydecane) (N-β( Aminoethyl) γ-aminopropyl trimethoxysilane). The above-mentioned adhesion aids may be used singly or in combination of several kinds.

在一實施例中,可進一步加入界面活性劑(surfactant)。基於感光性樹脂組成物為100重量份,界面活性劑的使用量可介於0.01~30重量份之間,較佳介於0.5~3重量份之間。界面活性劑例如是聚氧乙烯烷醚(polyoxyethylene alkyl ethers)(例如聚氧乙烯月桂醚(polyoxyethylene lauryl ether)、聚氧乙烯硬脂醚(polyoxyethylene stearyl ether)、聚氧乙烯油基醚(polyoxyethylene oleyl ether))、聚氧乙烯芳醚(polyoxyethylene aryl ethers)(例如聚氧乙烯辛基苯基醚(polyoxyethylene octyl phenyl ether)、壬基酚聚氧乙烯醚(polyoxyethylene nonyl phenyl ether))、聚乙烯乙二醇二烷基酯(polyethylene glycol dialkyl esters)(例如聚乙烯乙二醇二月桂酸(polyethylene glycol dilaurate)、聚乙烯乙二醇二硬脂酸(polyethylene glycol distearate))、有機矽氧烷聚合物(organosiloxane polymer)(例如KP341(由Shin-Etsu Chemical Industry Co.,Ltd.製造))或(甲基)丙烯酸聚合物((meth)acrylic acid polymer)(例如Polyflow No.75、90、95(由Kyoei-Sha Yushi Kagaku Kogyo Co.,Ltd.製造)、Megafac F171、F172、F173、F475(由Dainippon Chemicals ana Ink Co.,Ltd.製造)、Florard FC430、FC431(由Sumitomo 3M Co.,Ltd.製造)、Asahi Gard G710、Serflon S382、SC-101、SC-102、SC-103、Sc-104、SC-105、SC-1068(由Asahi Glass Co.,Ltd.製造))。上述之界面活性劑可單獨使用或混合數種使用。 In an embodiment, a surfactant may be further added. The surfactant may be used in an amount of from 0.01 to 30 parts by weight, preferably from 0.5 to 3 parts by weight, based on 100 parts by weight of the photosensitive resin composition. The surfactants are, for example, polyoxyethylene alkyl ethers (for example, polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene oleyl ether). )), polyoxyethylene aryl ethers (such as polyoxyethylene octyl phenyl ether, polyoxyethylene nonyl phenyl ether), polyethylene glycol Polyethylene glycol dialkyl esters (for example, polyethylene glycol dilaurate, polyethylene glycol distearate), organooxane polymer (organosiloxane) Polymer) (for example, KP341 (manufactured by Shin-Etsu Chemical Industry Co., Ltd.)) or (meth)acrylic acid polymer (for example, Polyflow No. 75, 90, 95 (by Kyoei- Sha Yushi Kagaku Kogyo Co., Ltd.), Megafac F171, F172, F173, F475 (manufactured by Dainippon Chemicals ana Ink Co., Ltd.), Florard FC430, FC431 (by Sumitomo 3M Co., Ltd.), Asahi Gard G710, Serflon S382, SC-101, SC-102, SC-103, Sc-104, SC-105, SC-1068 (manufactured by Asahi Glass Co., Ltd.). The above surfactants may be used singly or in combination of several kinds.

在一實施例中,還可進一步加入其它添加劑,例如消泡劑(deformer)、調平劑(leveling agent)、熱聚合抑制劑(thermal polymerization inhibitor agent)等。 In an embodiment, other additives such as a deformer, a leveling agent, and a thermal polymerization inhibitor may be further added. Polymerization inhibitor agent).

本發明的感光性樹脂組成物的製作主要是將上述(A)鹼可溶性樹脂膠合劑、(B)光聚合型含乙烯性不飽和基的化合物、(C)光起始劑、(D)有機酸酐、(E)分子中至少含有2個環氧基的化合物以及(F)有機溶劑於攪拌器中均勻混合成溶液狀態,其黏度介於1~200cps之間,較佳介於3~25cps之間。 The photosensitive resin composition of the present invention is mainly prepared by the above (A) alkali-soluble resin binder, (B) photopolymerizable ethylenically unsaturated group-containing compound, (C) photoinitiator, and (D) organic An acid anhydride, a compound having at least two epoxy groups in the (E) molecule, and (F) an organic solvent uniformly mixed into a solution state in a stirrer, the viscosity of which is between 1 and 200 cps, preferably between 3 and 25 cps. .

本發明的感光性樹脂組成物可藉由迴轉塗佈、流延塗佈、流延-迴轉塗佈等方式而塗佈於基板上。在塗佈之後,以80℃預烤(prebake)2分鐘,以將溶劑去除。然後,全面曝光200mJ/cm2。經過顯影之後,在230℃後烤20分鐘,以形成1~1.5μm的感光性樹脂層,並可作為彩色濾光片的保護膜。上述之基板例如為用於液晶顯示裝置的無鹼玻璃、鈉鈣玻璃、硬質玻璃(派勒斯玻璃)、石英玻璃或用於固體攝影裝置的光電變換裝置基板(如矽基板)等。 The photosensitive resin composition of the present invention can be applied onto a substrate by spin coating, cast coating, cast-spin coating or the like. After coating, it was prebaked at 80 ° C for 2 minutes to remove the solvent. Then, the full exposure was 200 mJ/cm 2 . After development, it was baked at 230 ° C for 20 minutes to form a photosensitive resin layer of 1 to 1.5 μm, and was used as a protective film for a color filter. The substrate described above is, for example, an alkali-free glass, a soda-lime glass, a hard glass (Pyles glass), a quartz glass, or a photoelectric conversion device substrate (for example, a germanium substrate) used for a solid-state imaging device.

本發明之結構式(1)將以下列(A)鹼可溶性樹脂膠合劑結構式(2A)的合成例為例對照進行說明,但是並不限於此例。其中,官能基a對照包括官能基h,官能基b對照包括官能基i,官能基x對照包括官能基c,官能基y對照包括d、e、f、g。 The structural formula (1) of the present invention will be described by taking a synthesis example of the following (A) alkali-soluble resin binder structural formula (2A) as an example, but is not limited thereto. Wherein the functional group a control comprises a functional group h, the functional group b control comprises a functional group i, the functional group x control comprises a functional group c, and the functional group y control comprises d, e, f, g.

(A)鹼可溶性樹脂膠合劑為結構式(2A)的合成例 (A) Alkali-soluble resin binder is a synthesis example of structural formula (2A)

其中c=1莫耳百分比;d=19莫耳百分比;e=3莫耳百分比;f=2莫耳百分比;g=30莫耳百分比;h=15莫耳百分比;i=30莫耳百分比。h+i=45莫耳百分比,於40~60莫耳百分比範圍內。 Wherein c = 1 mole percentage; d = 19 mole percentage; e = 3 mole percentage; f = 2 mole percentage; g = 30 mole percentage; h = 15 mole percentage; i = 30 mole percentage. h+i=45% of the mole, in the range of 40 to 60 moles.

此合成例的詳細合成步驟說明如下:在反應瓶中加入9克的2,2-偶氮雙異丁睛(2,2’-azobisisobutyronitrile,AIBN)、630克的PGMEA溶劑與10克的鏈轉移劑(α-甲基苯乙烯二聚物(α-methyl styrene dimer)),並攪拌溶解。然後,加入50.2克的甲基丙烯酸雙環戊酯(dicyclopentanylmethacrylate)、46.4克的甲基丙烯酸(methacrylic acid)、4.5克的甲基丙烯酸烯丙酯(allylmethacrylate)、1.6克的甲基丙烯腈(methacrylonitrile)、37.5克的苯乙烯(styrene)、2.9克的2,2-二甲基-1,3-丙二醇二甲基丙烯酸酯(2,2-dimethyl-1,3-propylene glycoldiacrylate),且通入氮氣並攪拌加熱到80℃來進行反應2.5小時。接著,將0.3克的 AIBN溶於10克的PGMEA中,並在10分鐘內滴入反應瓶以繼續反應12小時。之後,將氮氣停掉,加入51.2克的甲基丙烯酸酯(glycidyl methacrylate)、2.5克的催化劑(1-甲基咪唑(1-methylimidazole))與0.15克的抑制劑(4-甲氧基苯(4-methoxyphenol)),並於空氣中攪絆來進行反應19小時。所得的產物樹脂溶液的固含量為27.2wt.%;黏度為110cps/25℃;酸價為57.3mgKOH/g;重量平均分子量為11867。 The detailed synthetic procedure for this synthesis is illustrated as follows: 9 grams of 2,2-azobisisobutyronitrile (AIBN), 630 grams of PGMEA solvent and 10 grams of chain transfer were added to the reaction flask. agents (alpha] -methylstyrene dimer -methyl styrene dimer)), and stirred to dissolve. Then, 50.2 g of dicyclopentanylmethacrylate, 46.4 g of methacrylic acid, 4.5 g of allylmethacrylate, and 1.6 g of methacrylonitrile were added. 37.5 g of styrene, 2.9 g of 2,2-dimethyl-1,3-propane glycoldiacrylate, and nitrogen gas The mixture was heated to 80 ° C with stirring to carry out a reaction for 2.5 hours. Next, 0.3 g of AIBN was dissolved in 10 g of PGMEA, and dropped into the reaction flask over 10 minutes to continue the reaction for 12 hours. Thereafter, the nitrogen gas was stopped, and 51.2 g of glycidyl methacrylate, 2.5 g of a catalyst (1-methylimidazole) and 0.15 g of an inhibitor (4-methoxybenzene) were added. 4-methoxyphenol)), and the mixture was stirred in air for 19 hours. The obtained product resin solution had a solid content of 27.2 wt.%; a viscosity of 110 cps/25 ° C; an acid value of 57.3 mgKOH/g; and a weight average molecular weight of 11,867.

實施例1 Example 1

使用10重量份的具下列結構式(2A)的(A)鹼可溶性樹脂膠合劑, 其中c=1莫耳百分比;d=19莫耳百分比;e=3莫耳百分比;f=2莫耳百分比;g=30莫耳百分比;h=15莫耳百分比;i=30莫耳百分比。將2.7重量份的DPHA、0.5重量份的FBDE、0.25重量份的MA、0.2重量份的I-907、 0.5重量份的IPTX、0.02重量份的密著助劑GTS以及4重量份的溶劑PGMEA共同攪拌溶解混合,以調製而得彩色濾光片用的感光性樹脂組成物(表一)。此感光性樹脂組成物利用以下的各種測定評價方式來進行評價,所得結果如表二所示。 10 parts by weight of (A) alkali-soluble resin binder having the following structural formula (2A), Wherein c = 1 mole percentage; d = 19 mole percentage; e = 3 mole percentage; f = 2 mole percentage; g = 30 mole percentage; h = 15 mole percentage; i = 30 mole percentage. 2.7 parts by weight of DPHA, 0.5 parts by weight of FBDE, 0.25 parts by weight of MA, 0.2 parts by weight of I-907, 0.5 parts by weight of IPTX, 0.02 parts by weight of adhesion promoter GTS, and 4 parts by weight of solvent PGMEA together The mixture was stirred and dissolved to prepare a photosensitive resin composition for a color filter (Table 1). The photosensitive resin composition was evaluated by the following various measurement evaluation methods, and the results are shown in Table 2.

比較例1 Comparative example 1

使用10重量份的具下列結構式(2R)的(A)鹼可溶性樹脂膠合劑, 其中c=1.4莫耳百分比;d=23.5莫耳百分比;e=3.8莫耳百分比;f=2.6莫耳百分比;g=38.7莫耳百分比;h=15莫耳百分比;I=15莫耳百分比。將2.7重量份的DPHA、0.5重量份的FBDE、0.25重量份的MA、0.2重量份的I-907、0.5重量份的IPTX、0.02重量份的密著助劑GTS以及4重量份的溶劑PGMEA共同攪拌溶解混合,以調製 而得彩色濾光片用的感光性樹脂組成物(表一)。此感光性樹脂組成物利用以下的各種測定評價方式來進行評價,所得結果如表二所示。 10 parts by weight of (A) alkali-soluble resin binder having the following structural formula (2R), Wherein c = 1.4 mole percentage; d = 23.5 mole percentage; e = 3.8 mole percentage; f = 2.6 mole percentage; g = 38.7 mole percentage; h = 15 mole percentage; I = 15 mole percentage. 2.7 parts by weight of DPHA, 0.5 parts by weight of FBDE, 0.25 parts by weight of MA, 0.2 parts by weight of I-907, 0.5 parts by weight of IPTX, 0.02 parts by weight of adhesion promoter GTS, and 4 parts by weight of solvent PGMEA together The mixture was stirred and dissolved to prepare a photosensitive resin composition for a color filter (Table 1). The photosensitive resin composition was evaluated by the following various measurement evaluation methods, and the results are shown in Table 2.

評價方式: Evaluation method: 一、耐熱性 First, heat resistance

將所製得的玻璃基板上的感光性樹脂層於250℃烘箱處理60分鐘,並以profiler Tencor α-step 500量測處理前後的膜厚變化。 The photosensitive resin layer on the obtained glass substrate was oven-treated at 250 ° C for 60 minutes, and the film thickness change before and after the treatment was measured by profiler Tencor α -step 500.

○:厚度變化<6% ○: thickness change <6%

X:厚度變化≧6% X: thickness change ≧ 6%

二、耐鹼性 Second, alkali resistance

將所製得的玻璃基板上的感光性樹脂層於25℃±2℃下浸泡於10%的NaOH中3小時,並以profiler Tencor α-step 500量測處理前後的膜厚變化。 The photosensitive resin layer on the obtained glass substrate was immersed in 10% NaOH at 25 ° C ± 2 ° C for 3 hours, and the film thickness change before and after the treatment was measured by profiler Tencor α -step 500.

○:厚度變化<1% ○: thickness change <1%

X:厚度變化≧3% X: thickness change ≧3%

三、耐酸性 Third, acid resistance

將所製得的玻璃基板上的感光性樹脂層於25℃±2℃ 下浸泡於10%的HCl中3小時,並以profiler Tencor α-step 500量測處理前後的膜厚變化。 The photosensitive resin layer on the obtained glass substrate was immersed in 10% HCl for 3 hours at 25 ° C ± 2 ° C, and the film thickness change before and after the treatment was measured by profiler Tencor α -step 500.

○:厚度變化<1% ○: thickness change <1%

X:厚度變化≧3% X: thickness change ≧3%

四、耐溶劑性 Fourth, solvent resistance

將所製得的玻璃基板上的感光性樹脂層於25℃±2℃下浸泡於NMP中3小時,並以profiler Tencor α-step 500量測處理前後的膜厚變化。 The photosensitive resin layer on the obtained glass substrate was immersed in NMP at 25 ° C ± 2 ° C for 3 hours, and the film thickness change before and after the treatment was measured by profiler Tencor α -step 500.

○:厚度變化<1% ○: thickness change <1%

X:厚度變化≧3% X: thickness change ≧3%

四、透光度 Fourth, the transmittance

將所製得的玻璃基板上的感光性樹脂層以380~800nm波長的光測定光穿透率。 The photosensitive resin layer on the obtained glass substrate was measured for light transmittance at a wavelength of 380 to 800 nm.

○:透光率>97% ○: light transmittance >97%

X:透光率<97% X: light transmittance <97%

五、耐熱變色性 Five, heat discoloration

將所製得的玻璃基板上的感光性樹脂層於250℃烘箱處理60分鐘,並以380~800nm波長的光測定光透光率變化。 The photosensitive resin layer on the obtained glass substrate was oven-treated at 250 ° C for 60 minutes, and the light transmittance was measured by light having a wavelength of 380 to 800 nm.

○:光透光率變化5%以下 ○: The light transmittance is changed by 5% or less

△:光透光率變化5%~10% △: light transmittance changes by 5% to 10%

X:光透光率變化10%以上 X: Light transmittance changes by more than 10%

六、附著性 Sixth, adhesion

將所製得的玻璃基板上的感光性樹脂層進行十字切割(cross-cut)且藉由膠帶(adhesive tape)剝離膜層來進行測試。 The photosensitive resin layer on the obtained glass substrate was cross-cut and tested by peeling off the film layer by adhesive tape.

○:殘留的光阻膜超過98% ○: Residual photoresist film exceeds 98%

X:殘留的光阻膜少於98% X: Residual photoresist film is less than 98%

綜上所述,本發明之鹼可溶性樹脂膠合劑成功合成較高比例的官能基h與i,可以獲得更佳的耐熱性與耐鹼性,因此本發明之感光性樹脂組成物具有較高的透光度、耐熱性、耐酸性、耐鹼性與耐熱變色性等特性,且由此感光性樹脂組成物聚合而成的彩色濾光片的保護膜可以有效地保護彩色濾光片。此外,具有本發明之鹼可溶性樹脂膠合劑的感光樹脂膠合劑也同樣具有較高的透光度、耐熱性、耐酸性、耐鹼性與耐熱變色性等特性。 In summary, the alkali-soluble resin binder of the present invention successfully synthesizes a higher proportion of functional groups h and i, and can obtain better heat resistance and alkali resistance, so that the photosensitive resin composition of the present invention has a high The protective film of the color filter in which the photosensitive resin composition is polymerized by the characteristics of light transmittance, heat resistance, acid resistance, alkali resistance, and heat discoloration resistance can effectively protect the color filter. Further, the photosensitive resin binder having the alkali-soluble resin binder of the present invention also has characteristics such as high light transmittance, heat resistance, acid resistance, alkali resistance, and heat discoloration resistance.

雖然本發明已以實施例揭露如上,然其並非用以限定本發明,任何所屬技術領域中具有通常知識者,在不脫離本發明之精神和範圍內,當可作些許之更動與潤飾,故本 發明之保護範圍當視後附之申請專利範圍所界定者為準。 Although the present invention has been disclosed in the above embodiments, it is not intended to limit the invention, and any one of ordinary skill in the art can make some modifications and refinements without departing from the spirit and scope of the invention. this The scope of the invention is defined by the scope of the appended claims.

Claims (9)

一種感光性樹脂組成物,包括:(A)鹼可溶性樹脂膠合劑,含有由結構式(1)所表示的聚合物, 其中x=1~10莫耳百分比;y=29~59莫耳百分比;a+b=40~60莫耳百分比;a=15~40莫耳百分比;b=5~30莫耳百分比;R為苯甲基、苯基、CN或C(O)OR2,其中R2為C1~C15的直鏈或環狀烷基、苯基、苯甲基或烯丙基;R1為H或C1~C4的烷基;(B)光聚合型含乙烯性不飽和基的化合物;(C)光起始劑;(D)有機酸酐; (E)分子中至少含有2個環氧基的化合物;以及(F)有機溶劑,(F)有機溶劑為丙二醇甲醚醋酸酯、3-甲氧基乙酸丁酯、3-乙氧基丙酸乙酯或其組合,其中(A)鹼可溶性樹脂膠合劑的重量平均分子量介於3000~300000之間,(A)鹼可溶性樹脂膠合劑的酸價介於10~400mgKOH/g之間,以及該感光性樹脂組成物的黏度介於1~200cps之間。 A photosensitive resin composition comprising: (A) an alkali-soluble resin binder containing a polymer represented by the structural formula (1), Wherein x=1~10 mole percentage; y=29~59 mole percentage; a+b=40~60 mole percentage; a=15~40 mole percentage; b=5~30 mole percentage; R is Benzyl, phenyl, CN or C(O)OR2, wherein R2 is a C1 to C15 linear or cyclic alkyl group, a phenyl group, a benzyl group or an allyl group; and R 1 is H or a C1 to C4 group. (B) a photopolymerizable ethylenically unsaturated group-containing compound; (C) a photoinitiator; (D) an organic acid anhydride; (E) a compound having at least two epoxy groups in the molecule; An organic solvent, (F) an organic solvent is propylene glycol methyl ether acetate, 3-methoxyacetic acid butyl ester, 3-ethoxypropionic acid ethyl ester or a combination thereof, wherein (A) the alkali-soluble resin binder has an average weight The molecular weight is between 3,000 and 300,000. The acid value of the (A) alkali-soluble resin binder is between 10 and 400 mgKOH/g, and the viscosity of the photosensitive resin composition is between 1 and 200 cps. 如申請專利範圍第1項所述之感光性樹脂組成物,其中(A)鹼可溶性樹脂膠合劑的固含量介於10~50%之間。 The photosensitive resin composition according to claim 1, wherein the (A) alkali-soluble resin binder has a solid content of 10 to 50%. 如申請專利範圍第1項所述之感光性樹脂組成物,其中基於(A)鹼可溶性樹脂膠合劑為100重量份,(B)光聚合型含乙烯性不飽和基的化合物的含量介於1~250重量份之間。 The photosensitive resin composition according to claim 1, wherein the (B) alkali-soluble resin binder is 100 parts by weight, and the content of the (B) photopolymerizable ethylenically unsaturated group-containing compound is 1 ~250 parts by weight. 如申請專利範圍第1項所述之感光性樹脂組成物,其中基於(A)鹼可溶性樹脂膠合劑為100重量份,(C)光起始劑的含量介於0.1~100重量份之間。 The photosensitive resin composition according to claim 1, wherein the (A) alkali-soluble resin binder is contained in an amount of from 0.1 to 100 parts by weight based on 100 parts by weight of the (A) alkali-soluble resin binder. 如申請專利範圍第1項所述之感光性樹脂組成物,其中基於(A)鹼可溶性樹脂膠合劑為100重量份,(D)有機酸酐的含量介於0.1~100重量份之間。 The photosensitive resin composition according to claim 1, wherein the (A) alkali-soluble resin binder is contained in an amount of from 0.1 to 100 parts by weight based on 100 parts by weight of the (A) alkali-soluble resin binder. 如申請專利範圍第1項所述之感光性樹脂組成物,其中基於(A)鹼可溶性樹脂膠合劑為100重量份,(E)分子中至少含有2個環氧基的化合物的含量介於0.1~100重量份之間。 The photosensitive resin composition according to claim 1, wherein the content of the compound having at least two epoxy groups in the (E) molecule is 0.1 based on 100 parts by weight of the (A) alkali-soluble resin binder. ~100 parts by weight. 如申請專利範圍第1項所述之感光性樹脂組成物,其中基於(A)鹼可溶性樹脂膠合劑為100重量份,(F)有機溶劑的含量介於10~2500重量份之間。 The photosensitive resin composition according to claim 1, wherein the (A) alkali-soluble resin binder is contained in an amount of from 10 to 2,500 parts by weight based on 100 parts by weight of the (A) alkali-soluble resin binder. 一種彩色濾光片的保護膜,由申請專利範圍第1至7項中任一項所述之感光性樹脂組成物聚合而成。 A protective film of a color filter obtained by polymerizing a photosensitive resin composition according to any one of claims 1 to 7. 一種感光樹脂膠合劑,包括:(A)鹼可溶性樹脂膠合劑,含有由結構式(1)所表示的聚合物, 其中x=1~10莫耳百分比;y=29~59莫耳百分比;a+b=40~60莫耳百分比;a=15~40莫耳百分比;b=5~30莫耳百分比;R為苯甲基、苯基、CN或C(O)OR2,其中R2為C1~C15的直鏈或環狀烷基、苯基、苯甲基或烯丙基;R1為H或C1~C4的烷基; (B)光聚合型含乙烯性不飽和基的化合物;(C)光起始劑;(D)有機酸酐;(E)分子中至少含有2個環氧基的化合物;以及(F)有機溶劑,(F)有機溶劑為丙二醇甲醚醋酸酯、3-甲氧基乙酸丁酯、3-乙氧基丙酸乙酯或其組合,其中(A)鹼可溶性樹脂膠合劑的重量平均分子量介於3000~300000之間,以及(A)鹼可溶性樹脂膠合劑的酸價介於10~400mgKOH/g之間。 A photosensitive resin binder comprising: (A) an alkali-soluble resin binder containing a polymer represented by the formula (1), Wherein x=1~10 mole percentage; y=29~59 mole percentage; a+b=40~60 mole percentage; a=15~40 mole percentage; b=5~30 mole percentage; R is Benzyl, phenyl, CN or C(O)OR2, wherein R2 is a C1 to C15 linear or cyclic alkyl group, a phenyl group, a benzyl group or an allyl group; and R 1 is H or a C1 to C4 group. (B) a photopolymerizable ethylenically unsaturated group-containing compound; (C) a photoinitiator; (D) an organic acid anhydride; (E) a compound having at least two epoxy groups in the molecule; An organic solvent, (F) an organic solvent is propylene glycol methyl ether acetate, 3-methoxyacetic acid butyl ester, 3-ethoxypropionic acid ethyl ester or a combination thereof, wherein (A) the alkali-soluble resin binder has an average weight The molecular weight is between 3,000 and 300,000, and the acid value of the (A) alkali-soluble resin binder is between 10 and 400 mg KOH/g.
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