TW201714979A - Colored photosensitive resin composition and color filter using the same to ensure excellency in adhesion and peeling characteristics when a color filter is manufactured - Google Patents

Colored photosensitive resin composition and color filter using the same to ensure excellency in adhesion and peeling characteristics when a color filter is manufactured Download PDF

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TW201714979A
TW201714979A TW105126430A TW105126430A TW201714979A TW 201714979 A TW201714979 A TW 201714979A TW 105126430 A TW105126430 A TW 105126430A TW 105126430 A TW105126430 A TW 105126430A TW 201714979 A TW201714979 A TW 201714979A
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resin composition
photosensitive resin
colored photosensitive
color filter
alkali
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TW105126430A
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TWI670334B (en
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陸成焄
申鉉哲
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東友精細化工有限公司
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Materials For Photolithography (AREA)
  • Optical Filters (AREA)
  • Optics & Photonics (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymerisation Methods In General (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

The invention relates to a colored photosensitive resin composition and a color filter manufactured by using the same, more particularly, it relates to a colored photosensitive resin composition for a color filter which is used in manufacturing a color filter used in color liquid crystal display devices and a color filter manufactured by using the colored photosensitive resin composition. The colored photosensitive resin composition of the invention is characterized by being excellent in adhesion and peeling characteristics when used for manufacturing of the color filter.

Description

著色感光性樹脂組合物和使用其的濾色器 Coloring photosensitive resin composition and color filter using the same

本發明涉及著色感光性樹脂組合物和使用其的濾色器，更詳細地，涉及在製造彩色液晶顯示裝置等中使用的濾色器時使用的濾色器用著色感光性樹脂組合物和使用其製造的濾色器。 The present invention relates to a colored photosensitive resin composition and a color filter using the same, and more particularly to a colored photosensitive resin composition for a color filter used in the production of a color filter used in a color liquid crystal display device or the like, and a use thereof Manufactured color filter.

濾色器廣泛地用於攝像元件、液晶顯示裝置等，其應用範圍在急速地擴展。彩色液晶顯示裝置、攝像元件等中使用的濾色器通常通過以下製造：在黑矩陣圖案形成的基板上通過旋塗均勻地塗布含有相當於紅色、綠色和青色的各色的著色劑的著色感光性樹脂組合物後，對加熱乾燥(以下也有時稱為預燒成)而形成的塗膜進行曝光、顯影，根據需要進一步加熱固化(以下也有時稱為後燒成)，將該操作對每種色反複進行，形成各色的像素(韓國公開專利第10-1998-0010626號)。 Color filters are widely used for image pickup elements, liquid crystal display devices, etc., and their application range is rapidly expanding. A color filter used in a color liquid crystal display device, an image pickup element, or the like is generally produced by uniformly applying a coloring sensitivity of a coloring agent containing colors corresponding to red, green, and cyan by spin coating on a substrate formed of a black matrix pattern. After the resin composition, the coating film formed by heat drying (hereinafter sometimes referred to as pre-baking) is exposed and developed, and if necessary, further heated and cured (hereinafter sometimes referred to as post-baking), and the operation is performed for each. The color is repeated to form pixels of respective colors (Korean Patent Publication No. 10-1998-0010626).

另一方面，用著色感光性樹脂組合物製造濾色器時，在該技術領域中不斷要求研究密合性的提高和 剝離(peeling)特性的提高，現狀是與現有技術相比顯著地改善了密合性和剝離特性的著色感光性樹脂組合物尚未提出。 On the other hand, when a color filter is produced from a colored photosensitive resin composition, there is a continuing demand in the art to improve adhesion and The improvement of the peeling property is currently not proposed in the coloring photosensitive resin composition which remarkably improved the adhesiveness and peeling characteristics compared with the prior art.

現有技術文獻 Prior art literature 專利文獻 Patent literature

專利文獻1：韓國公開專利第10-1998-0010626號 Patent Document 1: Korean Patent Publication No. 10-1998-0010626

因此，本發明的目的在於提供在濾色器製造時在密合性和剝離特性的方面與現有技術相比得到了改善的著色感光性樹脂組合物和使用其的濾色器。 Accordingly, an object of the present invention is to provide a colored photosensitive resin composition which is improved in adhesion and peeling characteristics in comparison with the prior art in the production of a color filter, and a color filter using the same.

因此，本發明提供著色感光性樹脂組合物，其包含著色劑(A)、鹼可溶性樹脂(B)、光聚合性化合物(C)、光聚合引發劑(D)、和溶劑(E)，其特徵在於，上述鹼可溶性樹脂包含由下述化學式1表示的化合物和由下述化學式2表示的化合物，上述鹼可溶性樹脂的重均分子量為25,000~32,000，上述鹼可溶性樹脂的酸值為50~100mgKOH/g。 Accordingly, the present invention provides a colored photosensitive resin composition comprising a colorant (A), an alkali-soluble resin (B), a photopolymerizable compound (C), a photopolymerization initiator (D), and a solvent (E). The alkali-soluble resin includes a compound represented by the following Chemical Formula 1 and a compound represented by the following Chemical Formula 2, wherein the alkali-soluble resin has a weight average molecular weight of 25,000 to 32,000, and the alkali-soluble resin has an acid value of 50 to 100 mgKOH. /g.

[化學式1] [Chemical Formula 1]

上述化學式1中，R1各自獨立地為氫或碳數1~5的烷基， In the above Chemical Formula 1, R1 is each independently hydrogen or an alkyl group having 1 to 5 carbon atoms.

上述化學式2中，R2各自獨立地為氫或碳數1~5的烷基。 In the above Chemical Formula 2, R2 is each independently hydrogen or an alkyl group having 1 to 5 carbon atoms.

一實施方式可以是：著色劑(A)包含1種以上的綠色顏料或綠色染料。 In one embodiment, the colorant (A) may contain one or more kinds of green pigments or green dyes.

另一實施方式可以是：鹼可溶性樹脂包含由下述化學式3表示的化合物和由下述化學式4表示的化合物。 In another embodiment, the alkali-soluble resin may comprise a compound represented by the following Chemical Formula 3 and a compound represented by the following Chemical Formula 4.

[化學式3] [Chemical Formula 3]

另一實施方式可以是：以著色感光性樹脂組合物的固體成分總重量為基準，含有5~60重量%的上述著色劑(A)，含有10~80重量%的上述鹼可溶性樹脂(B)，含有5~50重量%的上述光聚合性化合物(C)，以鹼可溶性樹脂(B)和光聚合性化合物(C)的固體成分總重量為基準，含有0.1~40重量%的上述光聚合引發劑(D)，以著色感光性樹脂組合物的總重量為基準，含有60~90重量%的上述溶劑(E)。 In another embodiment, the coloring agent (A) may be contained in an amount of 5 to 60% by weight based on the total weight of the solid content of the colored photosensitive resin composition, and the alkali-soluble resin (B) may be contained in an amount of 10 to 80% by weight. The photopolymerizable compound (C) is contained in an amount of from 5 to 50% by weight, based on the total weight of the solid content of the alkali-soluble resin (B) and the photopolymerizable compound (C), and the photopolymerization initiation is contained in an amount of 0.1 to 40% by weight. The agent (D) contains 60 to 90% by weight of the above solvent (E) based on the total weight of the colored photosensitive resin composition.

另外，本發明提供使用上述著色感光性樹脂組合物製造的濾色器。 Further, the present invention provides a color filter produced by using the above colored photosensitive resin composition.

使用本發明的著色感光性樹脂組合物製造濾色器時密合性和剝離(peeling)特性優異是特徵所在。 When the color filter is produced by using the colored photosensitive resin composition of the present invention, the adhesiveness and the peeling property are excellent.

圖1表示剝離特性的評價標準。 Fig. 1 shows the evaluation criteria of the peeling characteristics.

本發明涉及著色感光性樹脂組合物，更詳細地，涉及在製造彩色液晶顯示裝置等中使用的濾色器時使用的濾色器用著色感光性樹脂組合物和使用其製造的濾色器。 The present invention relates to a colored photosensitive resin composition, and more particularly to a colored photosensitive resin composition for a color filter used in the production of a color filter used in a color liquid crystal display device or the like, and a color filter manufactured using the color filter.

以下對本發明詳細地說明。 The invention is explained in detail below.

著色劑(A) Colorant (A)

上述著色劑(A)以1種以上的顏料(a1)和1種以上的染料(a2)作為必要成分。 The coloring agent (A) contains one or more kinds of pigments (a1) and one or more kinds of dyes (a2) as essential components.

顏料(a1) Pigment (a1)

上述顏料(a1)可以使用該領域中一般使用的有機顏料或無機顏料。作為上述有機顏料，可以使用印刷油墨、噴墨油墨等中使用的各種的顏料。具體地，作為有機顏料，可列舉出水溶性偶氮顏料、不溶性偶氮顏料、酞菁顏料、喹吖啶酮顏料、異吲哚啉酮顏料、異吲哚啉顏料、苝顏料、苝酮顏料、二噁嗪顏料、蒽醌顏料、聯二蒽醌顏料、蒽嘧啶顏料、蒽酮(anthanthrone)顏料、陰丹酮(indanthrone)顏料、黃蒽酮顏料、皮蒽酮(pyranthrone)顏料、二酮基吡咯並吡咯顏料等。作為上述無機顏料，可列舉出金屬氧化物、金屬絡鹽等金屬化合物。具體地，作為無機顏料，可列舉鐵、鈷、鋁、鎘、鉛、銅、 鈦、鎂、鉻、鋅、銻、炭黑等金屬的氧化物或複合金屬氧化物等。特別地，作為上述有機顏料和無機顏料，具體地，可列舉出色指數(The society of Dyers and Colourists出版)中分類為顏料的化合物。更具體地，作為有機顏料和無機顏料，可列舉以下這樣的色指數(C.I.)序號的顏料，但未必限於這些。 As the above pigment (a1), an organic pigment or an inorganic pigment generally used in the field can be used. As the above organic pigment, various pigments used in printing inks, inkjet inks, and the like can be used. Specifically, examples of the organic pigment include a water-soluble azo pigment, an insoluble azo pigment, a phthalocyanine pigment, a quinacridone pigment, an isoindolinone pigment, an isoporphyrin pigment, an anthraquinone pigment, an anthrone pigment, and Dioxazine pigment, anthraquinone pigment, diterpene pigment, pyrith pyrimidine pigment, anthonerone pigment, indanthrone pigment, xanthone pigment, pyranthrone pigment, diketone Pyrrolopyrrole pigments, and the like. The inorganic pigment may, for example, be a metal compound such as a metal oxide or a metal complex salt. Specifically, examples of the inorganic pigment include iron, cobalt, aluminum, cadmium, lead, and copper. An oxide or a metal oxide of a metal such as titanium, magnesium, chromium, zinc, bismuth or carbon black. In particular, as the above organic pigment and inorganic pigment, specifically, a compound classified as a pigment in the excellent index (published by The Society of Dyers and Colourists) can be cited. More specifically, examples of the organic pigment and the inorganic pigment include the following color index (C.I.) number of pigments, but are not necessarily limited thereto.

C.I.顏料黃13、20、24、31、53、83、86、93、94、109、110、117、125、137、138、139、147、148、150、153、154、166、173、180、和185 CI Pigment Yellow 13, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 180 , and 185

C.I.顏料綠7、10、15、25、36、47、和58 C.I. Pigment Green 7, 10, 15, 25, 36, 47, and 58

上述顏料(a1)可以各自單獨地使用或者將2種以上組合使用。 These pigments (a1) may be used alone or in combination of two or more.

上述例示的C.I.顏料中，優選使用選自C.I.顏料黃138、C.I.顏料黃139、C.I.顏料黃150、C.I.顏料黃185、C.I.顏料綠7、C.I.顏料綠36、C.I.顏料綠58中的顏料。 Among the above-exemplified C.I. pigments, those selected from the group consisting of C.I. Pigment Yellow 138, C.I. Pigment Yellow 139, C.I. Pigment Yellow 150, C.I. Pigment Yellow 185, C.I. Pigment Green 7, C.I. Pigment Green 36, C.I. Pigment Green 58 are preferably used.

上述顏料優選使用其粒徑均一地分散的顏料分散液。作為用於使顏料的粒徑均一地分散的方法的一例，可列舉出含有顏料分散劑(a3)而進行分散處理的方法等。根據該方法，可以得到顏料在溶液中均一地分散的狀態的顏料分散液。 The above pigment is preferably a pigment dispersion liquid in which the particle diameter is uniformly dispersed. An example of a method for uniformly dispersing the particle diameter of the pigment is a method in which a pigment dispersant (a3) is contained and a dispersion treatment is performed. According to this method, a pigment dispersion liquid in a state in which the pigment is uniformly dispersed in the solution can be obtained.

作為上述顏料分散劑的具體例，可列舉出陽離子系、陰離子系、非離子系、兩性、聚酯系、多胺系等的表面活性劑等。這些可以各自單獨地使用或 者將2種以上組合使用。 Specific examples of the pigment dispersant include surfactants such as cationic, anionic, nonionic, amphoteric, polyester, and polyamine. These can be used individually or Two or more types are used in combination.

染料(a2) Dye (a2)

上述染料只要具有對於有機溶劑的溶解性，則可以無限制地使用。優選地，優選使用具有對於有機溶劑的溶解性、並且能夠確保對於鹼顯影液的溶解性和耐溶劑性、經時穩定性等的可靠性的染料。 The above dye can be used without limitation as long as it has solubility in an organic solvent. Preferably, it is preferable to use a dye having solubility in an organic solvent and ensuring reliability with respect to solubility and solvent resistance to an alkali developing solution, stability over time, and the like.

作為上述染料，可以使用選自具有磺酸、羧酸等酸性基團的酸性染料、酸性染料與含氮化合物的鹽、酸性染料的磺醯胺體等和它們的衍生物中的染料，此外，也可以選擇偶氮系、呫噸系、酞菁系的酸性染料和它們的衍生物。 As the dye, an acid dye selected from the group consisting of an acid dye having an acidic group such as a sulfonic acid or a carboxylic acid, a salt of an acid dye and a nitrogen-containing compound, a sulfonamide of an acid dye, and the like, and a dye thereof may be used. Azo dyes, xanthene systems, phthalocyanine acid dyes and derivatives thereof can also be selected.

優選地，上述染料可以列舉色指數(The Society of Dyers and Colourists出版)內分類為染料的化合物、染色筆記(由Shikisensha Co.，Ltd出版)中記載的公知的染料。 Preferably, the dye may be exemplified by a dye which is classified as a dye in the color index (published by The Society of Dyers and Colourists), and a known dye described in the dyeing note (published by Shikisensha Co., Ltd.).

作為上述染料的具體例，作為C.I.溶劑染料，可列舉出：C.I.溶劑黃4、14、15、16、21、23、24、38、56、62、63、68、79、82、93、94、98、99、151、162、163等黃色染料；C.I.溶劑綠1、3、4、5、7、28、29、32、33、34、35等綠色染料等。 Specific examples of the dye include CI solvent yellow 4, 14, 15, 16, 21, 23, 24, 38, 56, 62, 63, 68, 79, 82, 93, 94. , yellow dyes such as 98, 99, 151, 162, 163; CI solvent green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35 and other green dyes.

C.I.溶劑染料中，優選對於有機溶劑的溶解性優異的C.I.溶劑黃14、16、21、56、151、79、93；C.I.， 其中，更優選C.I.溶劑黃21、79；C.I.。 C.I. Solvent dyes, preferably C.I. Solvent Yellow 14, 16, 21, 56, 151, 79, 93; C.I., which is excellent in solubility in an organic solvent. Among them, C.I. Solvent Yellow 21, 79; C.I. is more preferred.

另外，作為C.I.酸性染料，可列舉出：C.I.酸性黃1、3、7、9、11、17、23、25、29、34、36、38、40、42、54、65、72、73、76、79、98、99、111、112、113、114、116、119、123、128、134、135、138、139、140、144、150、155、157、160、161、163、168、169、172、177、178、179、184、190、193、196、197、199、202、203、204、205、207、212、214、220、221、228、230、232、235、238、240、242、243、251等黃色染料；C.I.酸性綠1、3、5、9、16、25、27、50、58、63、65、80、104、105、106、109等綠色染料等。 Further, as the CI acid dye, CI acid yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, Yellow dyes such as 240, 242, 243, and 251; green dyes such as CI acid green 1, 3, 5, 9, 16, 25, 27, 50, 58, 63, 65, 80, 104, 105, 106, 109, and the like.

酸性染料中，優選對於有機溶劑的溶解度優異的C.I.酸性黃42；C.I.酸性綠27。 Among the acid dyes, C.I. Acid Yellow 42 which is excellent in solubility in an organic solvent; C.I. Acid Green 27 is preferable.

另外，作為C.I.直接染料，可列舉出：C.I.直接黃2、33、34、35、38、39、43、47、50、54、58、68、69、70、71、86、93、94、95、98、102、108、109、129、136、138、141等黃色染料；C.I.直接綠25、27、31、32、34、37、63、65、66、67、68、69、72、77、79、82等綠色染料等。 Further, as the CI direct dye, CI direct yellow 2, 33, 34, 35, 38, 39, 43, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, Yellow dyes such as 95, 98, 102, 108, 109, 129, 136, 138, 141; CI direct green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79, 82 and other green dyes.

進而，作為C.I.媒染染料，可列舉出：C.I.媒染黃5、8、10、16、20、26、30、31、33、42、43、45、56、61、62、65等黃色染料； C.I.媒染綠1、3、4、5、10、15、19、26、29、33、34、35、41、43、53等綠色染料等。 Further, as the C.I. mord dye, a yellow dye such as C.I. mordant yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65; C.I. mordant green 1, 3, 4, 5, 10, 15, 19, 26, 29, 33, 34, 35, 41, 43, 53 and other green dyes.

這些染料可以各自單獨地使用或者將2種以上組合使用。 These dyes may each be used singly or in combination of two or more.

顏料分散劑(a3) Pigment dispersant (a3)

上述顏料分散劑(a3)為了顏料的脫凝聚和穩定性維持而添加，可以無限制地使用該領域中一般使用的物質。優選地，含有包含BMA(甲基丙烯酸丁酯)或DMAEMA(甲基丙烯酸N，N-二甲基胺基乙酯)的丙烯酸酯系分散劑(以下稱為丙烯酸系分散劑)為宜。此時，上述丙烯酸系分散劑優選應用採用韓國公開專利第10-2004-0014311號中提出的活性控制方法製造的丙烯酸系分散劑。作為採用上述活性控制方法製造的丙烯酸酯系分散劑的市售品，可列舉出DISPER BYK-2000、DISPER BYK-2001、DISPER BYK-2070、DISPER BYK-2150等。 The pigment dispersant (a3) is added for the purpose of deagglomeration and stability maintenance of the pigment, and a substance generally used in the field can be used without limitation. Preferably, an acrylate-based dispersant (hereinafter referred to as an acrylic dispersant) containing BMA (butyl methacrylate) or DMAEMA (N,N-dimethylaminoethyl methacrylate) is preferably contained. In this case, the acrylic dispersant is preferably an acrylic dispersant produced by the activity control method proposed in Korean Laid-Open Patent Publication No. 10-2004-0014311. Commercial products of the acrylate-based dispersant produced by the above-described activity control method include DISPER BYK-2000, DISPER BYK-2001, DISPER BYK-2070, and DISPER BYK-2150.

上述例示的丙烯酸系分散劑可以各自單獨地使用或者將2種以上組合使用。 The acrylic dispersing agents exemplified above may be used singly or in combination of two or more kinds.

上述分散劑(a3)除了上述丙烯酸系分散劑以外，也可使用其他樹脂型的顏料分散劑。作為上述其他樹脂型的顏料分散劑，可列舉出公知的樹脂型的顏料分散劑，特別是聚胺甲酸酯、聚丙烯酸酯為代表的聚羧酸酯、不飽和聚醯胺、聚羧酸、聚羧酸的(部分的)胺鹽、聚羧酸的銨鹽、聚羧酸的烷基胺 鹽、聚矽氧烷、長鏈聚胺基醯胺磷酸鹽、含羥基的聚羧酸的酯以及它們的改性生成物、或者通過具有游離(free)的羧基的聚酯與聚(低級烯化亞胺)的反應形成的醯胺或它們的鹽這樣的油質的分散劑；(甲基)丙烯酸-苯乙烯共聚物、(甲基)丙烯酸-(甲基)丙烯酸酯共聚物、苯乙烯-馬來酸共聚物、聚乙烯醇或聚乙烯基吡咯烷酮這樣的水溶性樹脂或水溶性聚合物化合物；聚酯；改性聚丙烯酸酯；環氧乙烷/環氧丙烷的加成生成物和磷酸酯等。作為上述樹脂型分散劑的市售品，作為陽離子系樹脂分散劑，例如可列舉出BYK()社的商品名：DISPER BYK-160、DISPER BYK-161、DISPER BYK-162、DISPER BYK-163、DISPER BYK-164、DISPER BYK-166、DISPER BYK-171、DISPER BYK-182、DISPER BYK-184；BASF公司的商品名：EFKA-44、EFKA-46、EFKA-47、EFKA-48、EFKA-4010、EFKA-4050、EFKA-4055、EFKA-4020、EFKA-4015、EFKA-4060、EFKA-4300、EFKA-4330、EFKA-4400、EFKA-4406、EFKA-4510、EFKA-4800；Lubirzol公司的商品名：SOLSPERS-24000、SOLSPERS-32550、NBZ-4204/10；川研社的商品名：(HINOACT)T-6000、 T-7000、 T-8000；味之素社的商品名：(AJISPUR)PB-821、 PB-822、 PB-823；共榮社化學社的商品名：(FLORENE)DOPA-17HF、 DOPA-15BHF、 DOPA-33、 DOPA-44等。除了上述丙烯酸系分散劑以外，其他樹脂型的顏料分散劑可以各自單獨地使用或者將2種以上組合使用，可以與丙烯酸系分散劑並用而使用。 In addition to the above acrylic dispersant, the above dispersant (a3) may be a pigment dispersant of another resin type. Examples of the other resin type pigment dispersant include a known resin type pigment dispersant, in particular, a polycarboxylate represented by a polyurethane or a polyacrylate, an unsaturated polyamine, and a polycarboxylic acid. a (partial) amine salt of a polycarboxylic acid, an ammonium salt of a polycarboxylic acid, an alkylamine salt of a polycarboxylic acid, a polyoxyalkylene oxide, a long-chain polyamine phthalamide phosphate, a hydroxyl group-containing polycarboxylic acid An oily dispersant such as an ester and a modified product thereof, or a guanamine or a salt thereof formed by a reaction of a polyester having a free carboxyl group and a poly(lower alkyleneimine); Water-soluble resin such as acrylic acid-styrene copolymer, (meth)acrylic acid-(meth)acrylate copolymer, styrene-maleic acid copolymer, polyvinyl alcohol or polyvinylpyrrolidone or water-soluble polymerization Compound; polyester; modified polyacrylate; addition product of ethylene oxide/propylene oxide, phosphate ester, and the like. As a commercial product of the above-mentioned resin-type dispersing agent, as a cationic-type resin dispersing agent, BYK ( ) The trade name of the company: DISPER BYK-160, DISPER BYK-161, DISPER BYK-162, DISPER BYK-163, DISPER BYK-164, DISPER BYK-166, DISPER BYK-171, DISPER BYK-182, DISPER BYK-184; BASF's trade names: EFKA-44, EFKA-46, EFKA-47, EFKA-48, EFKA-4010, EFKA-4050, EFKA-4055, EFKA-4020, EFKA-4015, EFKA-4060, EFKA-4300, EFKA-4330, EFKA-4400, EFKA-4406, EFKA-4510, EFKA-4800; Lubirzol's trade name: SOLSPERS-24000, SOLSPERS-32550, NBZ-4204/10; Trade name of the company: (HINOACT) T-6000, T-7000, T-8000; Ajinomoto's trade name: (AJISPUR) PB-821, PB-822, PB-823; Trade name of Gongrongshe Chemical Society: (FLORENE) DOPA-17HF, DOPA-15BHF, DOPA-33, DOPA-44 and so on. In addition to the above-mentioned acrylic dispersant, the other resin type pigment dispersing agents may be used singly or in combination of two or more kinds, and may be used in combination with an acrylic dispersing agent.

上述分散劑(a3)的使用量，相對於使用的顏料(a1)的固體成分100重量份，為5~60重量份，更優選為15~50重量份的範圍。如果分散劑(a3)的含量按照上述基準超過60重量份，則黏度升高，不到5重量份的情況下，有時顏料的微粒化困難，或者分散後引起凝膠化等問題。 The amount of the dispersing agent (a3) to be used is 5 to 60 parts by weight, and more preferably 15 to 50 parts by weight, based on 100 parts by weight of the solid content of the pigment (a1) to be used. When the content of the dispersant (a3) exceeds 60 parts by weight based on the above-mentioned criteria, the viscosity is increased. When the content is less than 5 parts by weight, the pigment may be difficult to be microparticulated or may cause gelation after dispersion.

上述著色劑(A)的含量，相對於著色感光性樹脂組合物中的固體成分，以重量分率表示，含有5~60重量%、優選地10~45重量%為宜。按上述基準含有5~60重量%的上述著色劑(A)的情況下，即使形成薄膜，像素的色濃度也充分，顯影時非像素部的脫落性沒有降低，因此不易產生殘渣，因此優選。 The content of the coloring agent (A) is preferably 5 to 60% by weight, preferably 10 to 45% by weight, based on the solid content of the colored photosensitive resin composition. When the coloring agent (A) is contained in an amount of 5 to 60% by weight, the color density of the pixel is sufficient even when the film is formed, and the non-pixel portion is not deteriorated during development, so that it is less likely to cause residue, which is preferable.

本發明中，著色感光性樹脂組合物中的總固體成分含量，意味著從著色感光性樹脂組合物中將溶劑除去後剩餘的成分的總含量。 In the present invention, the total solid content in the colored photosensitive resin composition means the total content of the components remaining after removing the solvent from the colored photosensitive resin composition.

鹼可溶性樹脂(B) Alkali soluble resin (B)

上述鹼可溶性樹脂(B)包含由化學式1表示的化 合物和由化學式2表示的化合物。 The above alkali-soluble resin (B) contains the chemical represented by Chemical Formula 1. And a compound represented by Chemical Formula 2.

上述化學式1中，R1各自獨立地為氫或碳數1~5的烷基， In the above Chemical Formula 1, R1 is each independently hydrogen or an alkyl group having 1 to 5 carbon atoms.

上述化學式2中，R2各自獨立地為氫或碳數1~5的烷基。 In the above Chemical Formula 2, R2 is each independently hydrogen or an alkyl group having 1 to 5 carbon atoms.

上述鹼可溶性樹脂(B)的酸值可以為50~100mgKOH/g。不滿足上述範圍的情況下，在密合性和剝離特性的方面不能滿足該技術領域中要求的水準，著色感光性樹脂組合物難以確保充分的顯影速度，或者與基板的密合性減小，容易發生圖案的短路，經時穩定性降低，黏度容易上升。 The alkali-soluble resin (B) may have an acid value of 50 to 100 mgKOH/g. When the above range is not satisfied, the level required in the technical field cannot be satisfied in terms of adhesion and peeling characteristics, and it is difficult to ensure a sufficient development speed of the colored photosensitive resin composition or a decrease in adhesion to a substrate. The pattern is short-circuited, the stability is lowered over time, and the viscosity is easily increased.

上述鹼可溶性樹脂的重均分子量在通過GPC測定時，可以為25,000~32,000。不滿足上述範圍的情況下，在密合性和剝離特性的方面不能滿足該技術領域中要求的水準。 The weight average molecular weight of the above alkali-soluble resin may be 25,000 to 32,000 when measured by GPC. When the above range is not satisfied, the level required in the technical field cannot be satisfied in terms of adhesion and peeling characteristics.

為了確保上述鹼可溶性樹脂(B)的追加的顯影性，可以賦予羥基。 In order to ensure additional developability of the above alkali-soluble resin (B), a hydroxyl group can be provided.

上述鹼可溶性樹脂(B)，為了對於形成圖案時的顯影處理工序中使用的鹼顯影液具有可溶性，以具有羧基的烯屬不飽和單體(b1)作為必要成分進行共聚而製造。 The alkali-soluble resin (B) is produced by copolymerizing an ethylenically unsaturated monomer (b1) having a carboxyl group as an essential component in order to be soluble in the alkali developer used in the development treatment step in forming a pattern.

上述具有羧基的烯屬不飽和單體(b1)，作為具體例，可列舉出丙烯酸、甲基丙烯酸、巴豆酸等單羧酸類；富馬酸、中康酸、衣康酸等二羧酸類；和這些二羧酸的酸酐；ω-羧基聚己內酯單(甲基)丙烯酸酯等在兩末端具有羧基和羥基的聚合物的單(甲基)丙烯酸酯類等，優選丙烯酸、甲基丙烯酸。 The ethylenically unsaturated monomer (b1) having a carboxyl group, and specific examples thereof include monocarboxylic acids such as acrylic acid, methacrylic acid, and crotonic acid; and dicarboxylic acids such as fumaric acid, mesaconic acid, and itaconic acid; And an acid anhydride of these dicarboxylic acids; a mono(meth)acrylate of a polymer having a carboxyl group and a hydroxyl group at both terminals, such as ω-carboxypolycaprolactone mono(meth)acrylate, preferably acrylic acid, methacrylic acid .

為了對鹼可溶性樹脂(B)賦予羥基，可以使具有羧基的烯屬不飽和單體(b1)與具有羥基的烯屬不飽和單體(b2)共聚而製造，可以使具有縮水甘油基的化合物(b3)追加地與具有羧基的烯屬不飽和單體(b1)的共聚物反應而製造。另外，可以追加地使具有縮水甘油基的化合物(b3)與具有羧基的烯屬不飽和單體(b1)和具有羥基的烯屬不飽和單體(b2)的共聚物反應而製造。 In order to impart a hydroxyl group to the alkali-soluble resin (B), an ethylenically unsaturated monomer (b1) having a carboxyl group may be copolymerized with an ethylenically unsaturated monomer (b2) having a hydroxyl group to produce a compound having a glycidyl group. (b3) It is produced by additionally reacting with a copolymer of an ethylenically unsaturated monomer (b1) having a carboxyl group. Further, it can be produced by additionally reacting a compound having a glycidyl group (b3) with a copolymer of an ethylenically unsaturated monomer (b1) having a carboxyl group and an ethylenically unsaturated monomer (b2) having a hydroxyl group.

作為上述具有羥基的烯屬不飽和單體(b2)的具體例，優選(甲基)丙烯酸2-羥基乙酯、(甲基)丙烯酸2-羥基丙酯、(甲基)丙烯酸4-羥基丁酯、(甲基)丙烯酸2-羥基-3-苯氧基丙酯、N-羥基乙基丙烯醯胺等，優選(甲基)丙烯酸2-羥基乙酯。可以將這些的2種以上組合使用。 Specific examples of the ethylenically unsaturated monomer (b2) having a hydroxyl group are preferably 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, or 4-hydroxybutyl (meth)acrylate. The ester, 2-hydroxy-3-phenoxypropyl (meth)acrylate, N-hydroxyethylpropenylamine or the like is preferably 2-hydroxyethyl (meth)acrylate. Two or more of these may be used in combination.

作為上述具有縮水甘油基的化合物(b3)的具體例，有丁基縮水甘油基醚、縮水甘油基丙基醚、縮水甘油基苯基醚、2-乙基己基縮水甘油基醚、丁酸縮水甘油酯、縮水甘油基甲基醚、乙基縮水甘油基醚、縮水甘油基異丙基醚、叔丁基縮水甘油基醚、苄基縮水甘油基醚、縮水甘油基4-叔-丁基苯甲酸酯、硬脂酸縮水甘油酯、芳基縮水甘油基醚、甲基丙烯酸縮水甘油酯等，優選丁基縮水甘油基醚、芳基縮水甘油基醚、甲基丙烯酸縮水甘油酯。可以將這些的2種以上組合使用。 Specific examples of the glycidyl group-containing compound (b3) include butyl glycidyl ether, glycidyl propyl ether, glycidyl phenyl ether, 2-ethylhexyl glycidyl ether, and butyric acid shrinkage. Glyceryl ester, glycidyl methyl ether, ethyl glycidyl ether, glycidyl isopropyl ether, tert-butyl glycidyl ether, benzyl glycidyl ether, glycidyl 4-tert-butylbenzene A formate, a glycidyl stearate, an aryl glycidyl ether, a glycidyl methacrylate or the like is preferably a butyl glycidyl ether, an aryl glycidyl ether or a glycidyl methacrylate. Two or more of these may be used in combination.

鹼可溶性樹脂，相對於本發明的著色感光性樹脂組合物中的總固體成分含量，含有10~80重量%，優選含有10~70重量%。以上述含量含有的情況下，在顯影液中的溶解性充分，圖案形成容易，顯影時防止曝光部的像素部分的膜減少，非像素部分的脫落性變得良好，因此優選。 The alkali-soluble resin is contained in an amount of 10 to 80% by weight, preferably 10 to 70% by weight, based on the total solid content of the colored photosensitive resin composition of the present invention. When it is contained in the above content, the solubility in the developer is sufficient, the pattern formation is easy, and the film in the pixel portion of the exposed portion is prevented from being reduced during development, and the non-pixel portion is excellent in peeling property, which is preferable.

光聚合性化合物(C) Photopolymerizable compound (C)

上述光聚合性化合物(C)是在光和後述的光聚 合引發劑的作用下可聚合的化合物，可列舉出單官能單體、2官能單體、其他的多官能單體等。 The photopolymerizable compound (C) is a light and a light polymerization described later. Examples of the polymerizable compound by the action of the initiator include a monofunctional monomer, a bifunctional monomer, and other polyfunctional monomers.

作為上述單官能單體的具體例，可列舉出壬基苯基卡必醇丙烯酸酯、丙烯酸2-羥基-3-苯氧基丙酯、2-乙基己基卡必醇丙烯酸酯、丙烯酸2-羥基乙酯、N-乙烯基吡咯烷酮等。 Specific examples of the monofunctional monomer include mercaptophenylcarbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexyl carbitol acrylate, and acrylic acid 2- Hydroxyethyl ester, N-vinylpyrrolidone, and the like.

作為上述2官能單體的具體例，可列舉出1,6-己二醇二(甲基)丙烯酸酯、乙二醇二(甲基)丙烯酸酯、新戊二醇二(甲基)丙烯酸酯、三甘醇二(甲基)丙烯酸酯、雙酚A的雙(丙烯醯氧基乙基)醚、3-甲基戊二醇二(甲基)丙烯酸酯等。 Specific examples of the bifunctional monomer include 1,6-hexanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, and neopentyl glycol di(meth)acrylate. And triethylene glycol di(meth)acrylate, bis(acryloxyethyl)ether of bisphenol A, 3-methylpentanediol di(meth)acrylate, and the like.

作為其他的多官能單體的具體例，可列舉出三羥甲基丙烷三(甲基)丙烯酸酯、乙氧基化三羥甲基丙烷三(甲基)丙烯酸酯、丙氧基化三羥甲基丙烷三(甲基)丙烯酸酯、季戊四醇三(甲基)丙烯酸酯、季戊四醇四(甲基)丙烯酸酯、二季戊四醇五(甲基)丙烯酸酯、乙氧基化二季戊四醇六(甲基)丙烯酸酯、丙氧基化二季戊四醇六(甲基)丙烯酸酯、二季戊四醇六(甲基)丙烯酸酯等。 Specific examples of the other polyfunctional monomer include trimethylolpropane tri(meth)acrylate, ethoxylated trimethylolpropane tri(meth)acrylate, and propoxylated trihydroxyl. Methylpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, ethoxylated dipentaerythritol hexa(methyl) Acrylate, propoxylated dipentaerythritol hexa(meth) acrylate, dipentaerythritol hexa (meth) acrylate, and the like.

這些中，優選使用2官能以上的多官能單體。 Among these, a bifunctional or more polyfunctional monomer is preferably used.

光聚合性化合物(C)，相對於著色感光性樹脂組合物中的總固體成分含量，優選含有5~50重量%，更優選含有7~50重量%。以上述含量含有的情況下，像素部的強度和可靠性變得良好，因此優選。 The photopolymerizable compound (C) is preferably contained in an amount of 5 to 50% by weight, and more preferably 7 to 50% by weight based on the total solid content of the colored photosensitive resin composition. When it is contained in the above content, the strength and reliability of the pixel portion are good, which is preferable.

光聚合引發劑(D) Photopolymerization initiator (D)

上述光聚合引發劑(D)只要能夠使光聚合性化合物(C)聚合，可以對其種類無特別限制地使用。特別地，上述光聚合引發劑(D)從聚合特性、引發效率、吸收波長、獲得性、價格等的觀點出發，優選使用選自苯乙酮系化合物、二苯甲酮系化合物、三嗪系化合物、聯咪唑系化合物、肟化合物、和噻噸酮系化合物中的1種以上的化合物。 The photopolymerization initiator (D) can be used without particular limitation as long as it can polymerize the photopolymerizable compound (C). In particular, the photopolymerization initiator (D) is preferably selected from the group consisting of an acetophenone-based compound, a benzophenone-based compound, and a triazine-based compound from the viewpoints of polymerization characteristics, initiation efficiency, absorption wavelength, availability, and price. One or more compounds of the compound, the biimidazole compound, the hydrazine compound, and the thioxanthone compound.

作為上述苯乙酮系化合物的具體例，可列舉出二乙氧基苯乙酮、2-羥基-2-甲基-1-苯基丙烷-1-酮、苯偶醯二甲基縮酮、2-羥基-1-[4-(2-羥基乙氧基)苯基]-2-甲基丙烷-1-酮、1-羥基環己基苯基酮、2-甲基-1-(4-甲硫基苯基)-2-嗎啉代丙烷-1-酮、2-苄基-2-二甲基胺基-1-(4-嗎啉代苯基)丁烷-1-酮、2-羥基-2-甲基-1-[4-(1-甲基乙烯基)苯基]丙烷-1-酮、2-(4-甲基苄基)-2-(二甲基胺基)-1-(4-嗎啉代苯基)丁烷-1-酮等。 Specific examples of the acetophenone-based compound include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, and benzoin dimethyl ketal. 2-hydroxy-1-[4-(2-hydroxyethoxy)phenyl]-2-methylpropan-1-one, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1-(4- Methylthiophenyl)-2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)butan-1-one, 2 -hydroxy-2-methyl-1-[4-(1-methylvinyl)phenyl]propan-1-one, 2-(4-methylbenzyl)-2-(dimethylamino) 1-(4-morpholinophenyl)butan-1-one and the like.

作為上述二苯甲酮系化合物，例如有二苯甲酮、0-苯甲醯基苯甲酸甲酯、4-苯基二苯甲酮、4-苯甲醯基-4’-甲基二苯基硫醚、3,3’,4,4’-四(叔-丁基過氧羰基)二苯甲酮、2,4,6-三甲基二苯甲酮等。 Examples of the benzophenone-based compound include benzophenone, methyl 0-benzhydrylbenzoate, 4-phenylbenzophenone, and 4-benzylidene-4'-methyldiphenyl. A thioether, 3,3',4,4'-tetrakis(tert-butylperoxycarbonyl)benzophenone, 2,4,6-trimethylbenzophenone or the like.

作為上述三嗪系化合物的具體例，可列舉出2,4-雙(三氯甲基)-6-(4-甲氧基苯基)-1,3,5-三嗪、2,4-雙(三氯甲基)-6-(4-甲氧基萘基)-1,3,5-三嗪、 2,4-雙(三氯甲基)-6-胡椒基-1,3,5-三嗪、2,4-雙(三氯甲基)-6-(4-甲氧基苯乙烯基)-1,3,5-三嗪、2,4-雙(三氯甲基)-6-[2-(5-甲基呋喃-2-基)乙烯基]-1,3,5-三嗪、2,4-雙(三氯甲基)-6-[2-(呋喃-2-基)乙烯基]-1,3,5-三嗪、2,4-雙(三氯甲基)-6-[2-(4-二乙基胺基-2-甲基苯基)乙烯基]-1,3,5-三嗪、2,4-雙(三氯甲基)-6-[2-(3,4-二甲氧基苯基)乙烯基]-1,3,5-三嗪等。 Specific examples of the triazine-based compound include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine and 2,4-. Bis(trichloromethyl)-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperidin-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl) -1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(5-methylfuran-2-yl)vinyl]-1,3,5-triazine , 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)- 6-[2-(4-Diethylamino-2-methylphenyl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2 -(3,4-Dimethoxyphenyl)vinyl]-1,3,5-triazine, and the like.

作為上述聯咪唑化合物的具體例，可列舉出2,2’-雙(2-氯苯基)-4,4’,5,5’-四苯基聯咪唑、2,2’-雙(2,3-二氯苯基)-4,4’,5,5’-四苯基聯咪唑、2,2’-雙(2-氯苯基)-4,4’,5,5’-四(烷氧基苯基)聯咪唑、2,2’-雙(2-氯苯基)-4,4’,5,5’-四(三烷氧基苯基)聯咪唑、2,2-雙(2,6-二氯苯基)-4,4’,5,5’-四苯基-1,2’-聯咪唑或4,4’,5,5’位的苯基被烷氧羰基取代的咪唑化合物等。這些中，優選使用2,2’-雙(2-氯苯基)-4,4’,5,5’-四苯基聯咪唑、2,2’-雙(2,3-二氯苯基)-4,4’,5,5’-四苯基聯咪唑、2,2-雙(2,6-二氯苯基)-4,4’,5,5’-四苯基-1,2’-聯咪唑。 Specific examples of the biimidazole compound include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, and 2,2'-bis (2). ,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-four (alkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetrakis(trialkoxyphenyl)biimidazole, 2,2- Bis(2,6-dichlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole or 4,4',5,5' phenyl group by alkoxy A carbonyl-substituted imidazole compound or the like. Among these, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl) is preferably used. -4,4',5,5'-tetraphenylbiimidazole, 2,2-bis(2,6-dichlorophenyl)-4,4',5,5'-tetraphenyl-1, 2'-biimidazole.

作為上述肟化合物的具體例，可列舉出o-乙氧基羰基-α-氧亞胺基-1-苯基丙烷-1-酮等，作為市售品，巴斯夫公司的OXE01、OXE02是代表性的。 Specific examples of the above-mentioned oxime compound include o-ethoxycarbonyl-α-oxyimino-1-phenylpropan-1-one, and as a commercial product, OXE01 and OXE02 of BASF are representative. of.

作為上述噻噸酮系化合物，例如有2-異丙基噻噸酮、2,4-二乙基噻噸酮、2,4-二氯噻噸酮、1-氯-4-丙氧基噻噸酮等。 As the above thioxanthone-based compound, for example, 2-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, 1-chloro-4-propoxythiophene Tons of ketone and so on.

另外，上述光聚合引發劑(D)，為了提高本發明的著色感光性樹脂組合物的感度，可以進一步包含光聚合引發輔助劑。本發明涉及的著色感光性樹脂組合物通過含有光聚合引發輔助劑，感度進一步提高，能夠提高生產率。 In addition, the photopolymerization initiator (D) may further contain a photopolymerization initiation aid in order to improve the sensitivity of the coloring photosensitive resin composition of the present invention. When the colored photosensitive resin composition of the present invention contains a photopolymerization initiation aid, the sensitivity is further improved, and productivity can be improved.

上述光聚合引發輔助劑優選使用例如選自胺化合物、羧酸化合物、具有硫醇基的有機硫化合物中的1種以上的化合物。 As the photopolymerization initiation aid, for example, one or more compounds selected from the group consisting of an amine compound, a carboxylic acid compound, and an organic sulfur compound having a thiol group are preferably used.

作為上述胺化合物，優選使用芳香族胺化合物，具體地，可以使用三乙醇胺、甲基二乙醇胺、三異丙醇胺等脂肪族胺化合物、4-二甲基胺基苯甲酸甲酯、4-二甲基胺基苯甲酸乙酯、4-二甲基胺基苯甲酸異戊酯、4-二甲基胺基苯甲酸2-乙基己酯、苯甲酸2-二甲基胺基乙酯、N,N-二甲基對甲苯胺、4,4’-雙(二甲基胺基)二苯甲酮(通稱：米蚩酮)、4,4’-雙(二乙基胺基)二苯甲酮等。 As the above amine compound, an aromatic amine compound is preferably used. Specifically, an aliphatic amine compound such as triethanolamine, methyldiethanolamine or triisopropanolamine, methyl 4-dimethylaminobenzoate or the like can be used. Ethyl dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-ethylhexyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate , N,N-dimethyl-p-toluidine, 4,4'-bis(dimethylamino)benzophenone (general name: Michler's ketone), 4,4'-bis(diethylamino) Benzophenone and the like.

上述羧酸化合物優選為芳香族雜醋酸類，具體地，可列舉出苯基硫代醋酸、甲基苯基硫代醋酸、乙基苯基硫代醋酸、甲基乙基苯基硫代醋酸、二甲基苯基硫代醋酸、甲氧基苯基硫代醋酸、二甲氧基苯基硫代醋酸、氯苯基硫代醋酸、二氯苯基硫代醋酸、N-苯基甘胺酸、苯氧基醋酸、萘基硫代醋酸、N-萘基甘胺酸、萘氧基醋酸等。 The carboxylic acid compound is preferably an aromatic heteroacetic acid, and specific examples thereof include phenylthioacetic acid, methylphenylthioacetic acid, ethylphenylthioacetic acid, and methylethylphenylthioacetic acid. Dimethylphenylthioacetic acid, methoxyphenylthioacetic acid, dimethoxyphenylthioacetic acid, chlorophenylthioacetic acid, dichlorophenylthioacetic acid, N-phenylglycine , phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, naphthyloxyacetic acid, and the like.

作為上述具有硫醇基的有機硫化合物的具體 例，可列舉出2-巰基苯并噻唑、1,4-雙(3-巰基丁醯氧基)丁烷、1,3,5-三(3-巰基丁氧基乙基)-1,3,5-三嗪-2,4,6(1H,3H,5H)-三酮、三羥甲基丙烷三(3-巰基丙酸酯)、季戊四醇四(3-巰基丁酸酯)、季戊四醇四(3-巰基丙酸酯)、二季戊四醇六(3-巰基丙酸酯)、四甘醇雙(3-巰基丙酸酯)等。 Specific to the above organic sulfur compound having a thiol group For example, 2-mercaptobenzothiazole, 1,4-bis(3-mercaptobutoxy)butane, 1,3,5-tris(3-mercaptobutoxyethyl)-1,3 , 5-triazine-2,4,6(1H,3H,5H)-trione, trimethylolpropane tris(3-mercaptopropionate), pentaerythritol tetrakis(3-mercaptobutyrate), pentaerythritol IV (3-mercaptopropionate), dipentaerythritol hexa(3-mercaptopropionate), tetraethylene glycol bis(3-mercaptopropionate), and the like.

將上述光聚合引發劑與光聚合引發輔助劑一起使用的情況下，光聚合引發輔助劑的含量相對於光聚合引發劑1摩爾，優選為10摩爾以下，更優選為0.01~5摩爾。以上述含量使用光聚合引發輔助劑的情況下，著色感光性樹脂組合物的感度進一步提高，存在使用該組合物形成的濾色器的生產率提高的傾向，因此優選。 When the photopolymerization initiator is used together with the photopolymerization initiator, the content of the photopolymerization initiator is preferably 10 mol or less, and more preferably 0.01 to 5 mol, per mol of the photopolymerization initiator. When the photopolymerization initiation aid is used in the above-mentioned content, the sensitivity of the colored photosensitive resin composition is further improved, and the productivity of the color filter formed using the composition tends to be improved, which is preferable.

光聚合引發劑(D)，相對於本發明的鹼可溶性樹脂(B)和光聚合性化合物(C)的總固體成分含量，包含0.1~40重量%、優選地1~30重量%。以上述含量含有的情況下，使著色感光性樹脂組合物高感度化，曝光時間縮短，生產率提高，能夠維持高解析度，因此優選。另外，使用上述的條件的組合物形成的像素部的強度與上述像素部的表面中的平滑性變得良好。 The photopolymerization initiator (D) is contained in an amount of 0.1 to 40% by weight, preferably 1 to 30% by weight, based on the total solid content of the alkali-soluble resin (B) and the photopolymerizable compound (C) of the present invention. When it is contained in the above-mentioned content, it is preferable because the coloring photosensitive resin composition is highly sensitive, the exposure time is shortened, productivity is improved, and high resolution can be maintained. Moreover, the intensity of the pixel portion formed using the composition of the above-described conditions and the smoothness in the surface of the above-described pixel portion become good.

溶劑(E) Solvent (E)

上述溶劑(E)只要對於使著色感光性樹脂組合物中所含的其他成分溶解有效，則可以無特別限制 地使用通常的著色感光性樹脂組合物中使用的溶劑，特別優選醚類、芳香族烴類、酮類、醇類、酯類、或醯胺類等。 The solvent (E) is not particularly limited as long as it is effective for dissolving other components contained in the colored photosensitive resin composition. The solvent used in the usual colored photosensitive resin composition is used, and ethers, aromatic hydrocarbons, ketones, alcohols, esters, guanamines and the like are particularly preferable.

上述溶劑(E)，具體地，可列舉出：乙二醇單甲基醚、乙二醇單乙基醚、乙二醇單丙基醚、乙二醇單丁基醚等乙二醇單烷基醚類、二甘醇二甲基醚、二甘醇二乙基醚、二甘醇二丙基醚、二甘醇二丁基醚等二甘醇二烷基醚類、甲基溶纖劑乙酸酯、乙基溶纖劑乙酸酯等乙二醇烷基醚乙酸酯類、丙二醇單甲基醚乙酸酯、丙二醇單乙基醚乙酸酯、丙二醇單丙基醚乙酸酯、甲氧基丁基乙酸酯、甲氧基戊基乙酸酯等伸烷基二醇烷基醚乙酸酯類、苯、甲苯、二甲苯、均三甲苯等芳香族烴類、甲基乙基酮、丙酮、甲基戊基酮、甲基異丁基酮、環己酮等酮類、乙醇、丙醇、丁醇、己醇、環己醇、乙二醇、甘油等醇類、3-乙氧基丙酸乙酯、3-甲氧基丙酸甲酯等酯類、γ-丁內酯等環狀酯類等。 Specific examples of the solvent (E) include ethylene glycol monoalkane such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, and ethylene glycol monobutyl ether. Diethylene glycol dialkyl ethers such as ethers, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, methyl cellosolve Ethylene glycol alkyl ether acetate such as acetate or ethyl cellosolve acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, Alkyl diol alkyl ether acetate such as methoxybutyl acetate or methoxypentyl acetate, aromatic hydrocarbons such as benzene, toluene, xylene, and mesitylene, methyl ethyl Ketones such as ketone, acetone, methyl amyl ketone, methyl isobutyl ketone, cyclohexanone, alcohols such as ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, glycerol, etc. 3- An ester such as ethyl ethoxypropionate or methyl 3-methoxypropionate; or a cyclic ester such as γ-butyrolactone.

上述溶劑(E)在塗布性和乾燥性的方面，優選沸點為100℃~200℃的有機溶劑，更優選地，可以使用丙二醇單甲基醚乙酸酯、丙二醇單乙基醚乙酸酯、環己酮、乳酸乙酯、乳酸丁酯、3-乙氧基丙酸 乙酯、3-甲氧基丙酸甲酯等。 The solvent (E) is preferably an organic solvent having a boiling point of from 100 ° C to 200 ° C in terms of coatability and drying property, and more preferably propylene glycol monomethyl ether acetate or propylene glycol monoethyl ether acetate. Cyclohexanone, ethyl lactate, butyl lactate, 3-ethoxypropionic acid Ethyl ester, methyl 3-methoxypropionate, and the like.

上述例示的溶劑(E)可以各自單獨地使用或者將2種以上混合使用，以本發明的著色感光性樹脂組合物的總重量為基準，包含60~90重量%、優選地70~85重量%。如果上述溶劑(E)為上述的60~90重量%的範圍，採用輥塗機、旋塗機、狹縫和旋轉塗布機、狹縫塗布機(有時也稱為模壓塗布機)、噴墨等塗布裝置塗布時，提供塗布性變得良好的效果。 The solvent (E) exemplified above may be used singly or in combination of two or more kinds, and is contained in an amount of 60 to 90% by weight, preferably 70 to 85% by weight based on the total weight of the colored photosensitive resin composition of the present invention. . If the solvent (E) is in the range of 60 to 90% by weight as described above, a roll coater, a spin coater, a slit and a spin coater, a slit coater (sometimes referred to as a press coater), and an ink jet are used. When the coating device is applied, the coating property is improved.

另外，本發明的著色感光性樹脂組合物可以追加地包含添加劑，上述添加劑可以根據需要選擇性地添加，例如可列舉出固化劑、表面活性劑、密合促進劑、抗氧化劑、紫外線吸收劑、防凝聚劑等。 In addition, the colored photosensitive resin composition of the present invention may further contain an additive, and the additive may be optionally added as needed, and examples thereof include a curing agent, a surfactant, an adhesion promoter, an antioxidant, and an ultraviolet absorber. Anti-agglomerating agent, etc.

本發明的著色感光性樹脂組合物例如可以採用以下這樣的方法製造。預先將著色劑與溶劑混合，使用珠磨機等使其分散直至著色劑的平均粒徑成為0.2μm以下左右。此時，根據需要使用顏料分散劑，另外，也有時配合鹼可溶性樹脂的一部分或全部。在得到的分散液(以下也有時稱為“混煉基料”)中進一步添加鹼可溶性樹脂的剩餘部分、光聚合性化合物、光聚合引發劑、和反應性有機矽系表面活性劑、根據需要使用的其他成分、根據需要追加的溶劑以成為規定的濃度，得到目標的著色感光性樹脂組合物。 The colored photosensitive resin composition of the present invention can be produced, for example, by the following method. The colorant is mixed with a solvent in advance, and dispersed by a bead mill or the like until the average particle diameter of the colorant is about 0.2 μm or less. At this time, a pigment dispersing agent is used as needed, and some or all of the alkali-soluble resin may be blended. Further, the remaining portion of the alkali-soluble resin, the photopolymerizable compound, the photopolymerization initiator, and the reactive organic lanthanide surfactant are added to the obtained dispersion (hereinafter sometimes referred to as "kneaded base"), as needed The other components to be used and the solvent to be added as needed are brought to a predetermined concentration to obtain a desired colored photosensitive resin composition.

另外，本發明提供使用上述著色感光性樹脂組 合物製造的濾色器。 Further, the present invention provides the use of the above colored photosensitive resin group A color filter made of the compound.

以下使用合成例、實施例、比較例和實驗例對本發明詳細地說明。但是，下述的合成例、實施例、比較例和實驗例用於對本發明進行例示，本發明並不由下述的合成例、實施例、比較例和實驗例限定，可以進行多種修正和改變。另外，以下的合成例、實施例和比較例中，表示含量的“%”和“份”只要無特別說明，則為重量基準。 Hereinafter, the present invention will be described in detail using synthesis examples, examples, comparative examples and experimental examples. However, the following synthesis examples, examples, comparative examples, and experimental examples are intended to illustrate the present invention, and the present invention is not limited by the following synthesis examples, examples, comparative examples, and experimental examples, and various modifications and changes can be made. In the following synthesis examples, examples, and comparative examples, "%" and "parts" indicating the content are based on weight unless otherwise specified.

合成例1. A-1的合成Synthesis Example 1. Synthesis of A-1

在具備攪拌器、溫度計、回流冷卻管、滴液漏斗和氮導入管的1000ml燒瓶中投入丙二醇單甲基醚乙酸酯400份、AIBN 7份、甲基丙烯酸苄酯(BZMA、化學式3)45份、甲基丙烯酸三環癸酯(TCDMA、化學式4)58份、甲基丙烯酸酯20份、甲基丙烯酸30份，氮置換。然後攪拌，使反應液的溫度上升到120℃，上升後反應15小時。這樣合成的鹼可溶性樹脂的最終固體成分為31.0%，固體成分的酸值為80mgKOH/g，用GPC測定的重均分子量為27,000(表1)。 In a 1000 ml flask equipped with a stirrer, a thermometer, a reflux cooling tube, a dropping funnel, and a nitrogen introduction tube, 400 parts of propylene glycol monomethyl ether acetate, 7 parts of AIBN, and benzyl methacrylate (BZMA, Chemical Formula 3) 45 were placed. A portion, 58 parts of tricyclodecyl methacrylate (TCDMA, Chemical Formula 4), 20 parts of methacrylate, 30 parts of methacrylic acid, and nitrogen substitution. Then, the temperature of the reaction liquid was raised to 120 ° C with stirring, and the reaction was raised for 15 hours. The alkali-soluble resin thus synthesized had a final solid content of 31.0%, an acid value of a solid component of 80 mgKOH/g, and a weight average molecular weight measured by GPC of 27,000 (Table 1).

[化學式4] [Chemical Formula 4]

合成例2. A-2的合成Synthesis Example 2. Synthesis of A-2

在具備攪拌器、溫度計、回流冷卻管、滴液漏斗和氮導入管的1000ml燒瓶中投入丙二醇單甲基醚乙酸酯400份、AIBN 7份、甲基丙烯酸苄酯(化學式3)45份、甲基丙烯酸三環癸酯(化學式4)58份、甲基丙烯酸酯20份、甲基丙烯酸32份，進行氮置換。然後攪拌，使反應液的溫度上升到120℃，上升後反應17小時。這樣合成的鹼可溶性樹脂的最終固體成分為31.0%，固體成分的酸值為95mgKOH/g，通過GPC測定的重均分子量為30,000(表1)。 400 parts of propylene glycol monomethyl ether acetate, 7 parts of AIBN, and 45 parts of benzyl methacrylate (chemical formula 3) were placed in a 1000 ml flask equipped with a stirrer, a thermometer, a reflux cooling tube, a dropping funnel, and a nitrogen introduction tube. 58 parts of tricyclodecyl methacrylate (chemical formula 4), 20 parts of methacrylate, and 32 parts of methacrylic acid were subjected to nitrogen substitution. Then, the temperature of the reaction liquid was raised to 120 ° C with stirring, and the reaction was raised for 17 hours. The alkali-soluble resin thus synthesized had a final solid content of 31.0%, an acid value of a solid component of 95 mgKOH/g, and a weight average molecular weight measured by GPC of 30,000 (Table 1).

合成例3. A-3的合成Synthesis Example 3. Synthesis of A-3

在具備攪拌器、溫度計、回流冷卻管、滴液漏斗和氮導入管的1000ml燒瓶中投入丙二醇單甲基醚乙酸酯400份、AIBN 7部、甲基丙烯酸苄酯(化學式3)45份、甲基丙烯酸三環癸酯(化學式4)58份、甲基丙烯酸酯20份、甲基丙烯酸30份，進行氮置換。然後攪拌，使反應液的溫度上升到120℃，上升後反應10小時。這樣合成的鹼可溶性樹脂的最終固體成分 為31.0%，固體成分的酸值為80mgKOH/g，通過GPC測定的重均分子量為20,000(表1)。 400 parts of propylene glycol monomethyl ether acetate, 7 parts of AIBN, and 45 parts of benzyl methacrylate (chemical formula 3) were placed in a 1000 ml flask equipped with a stirrer, a thermometer, a reflux cooling tube, a dropping funnel, and a nitrogen introduction tube. 58 parts of tricyclodecyl methacrylate (chemical formula 4), 20 parts of methacrylate, and 30 parts of methacrylic acid were subjected to nitrogen substitution. Then, the temperature of the reaction liquid was raised to 120 ° C with stirring, and the reaction was carried out for 10 hours. The final solid component of the alkali-soluble resin thus synthesized It was 31.0%, the acid value of the solid content was 80 mgKOH/g, and the weight average molecular weight measured by GPC was 20,000 (Table 1).

合成例4. A-4的合成Synthesis Example 4. Synthesis of A-4

在具備攪拌器、溫度計、回流冷卻管、滴液漏斗和氮導入管的1000ml燒瓶中投入丙二醇單甲基醚乙酸酯400份、AIBN 7份、甲基丙烯酸苄酯(化學式3)45份、甲基丙烯酸三環癸酯(化學式4)58份、甲基丙烯酸酯20份、甲基丙烯酸32份，進行氮置換。然後攪拌，使反應液的溫度上升到120℃，上升後反應10小時。這樣合成的鹼可溶性樹脂的最終固體成分為31.0%，固體成分的酸值為95mgKOH/g，通過GPC測定的重均分子量為20,000(表1)。 400 parts of propylene glycol monomethyl ether acetate, 7 parts of AIBN, and 45 parts of benzyl methacrylate (chemical formula 3) were placed in a 1000 ml flask equipped with a stirrer, a thermometer, a reflux cooling tube, a dropping funnel, and a nitrogen introduction tube. 58 parts of tricyclodecyl methacrylate (chemical formula 4), 20 parts of methacrylate, and 32 parts of methacrylic acid were subjected to nitrogen substitution. Then, the temperature of the reaction liquid was raised to 120 ° C with stirring, and the reaction was carried out for 10 hours. The alkali-soluble resin thus synthesized had a final solid content of 31.0%, an acid value of a solid component of 95 mgKOH/g, and a weight average molecular weight measured by GPC of 20,000 (Table 1).

合成例5. A-5的合成Synthesis Example 5. Synthesis of A-5

在具備攪拌器、溫度計、回流冷卻管、滴液漏斗和氮導入管的1000ml燒瓶中投入丙二醇單甲基醚乙酸酯400份、AIBN 7份、甲基丙烯酸苄酯(化學式3)45份、甲基丙烯酸三環癸酯(化學式4)58份、甲基丙烯酸酯20份、甲基丙烯酸32份，進行氮置換。然後攪拌，使反應液的溫度上升到120℃，上升後反應12小時。這樣合成的鹼可溶性樹脂的最終固體成分為31.0%，固體成分的酸值為95mgKOH/g，通過GPC測定的重均分子量為24,000(表1)。 400 parts of propylene glycol monomethyl ether acetate, 7 parts of AIBN, and 45 parts of benzyl methacrylate (chemical formula 3) were placed in a 1000 ml flask equipped with a stirrer, a thermometer, a reflux cooling tube, a dropping funnel, and a nitrogen introduction tube. 58 parts of tricyclodecyl methacrylate (chemical formula 4), 20 parts of methacrylate, and 32 parts of methacrylic acid were subjected to nitrogen substitution. Then, the temperature of the reaction liquid was raised to 120 ° C with stirring, and the reaction was carried out for 12 hours. The alkali-soluble resin thus synthesized had a final solid content of 31.0%, an acid value of a solid component of 95 mgKOH/g, and a weight average molecular weight measured by GPC of 24,000 (Table 1).

合成例6. A-6的合成Synthesis Example 6. Synthesis of A-6

在具備攪拌器、溫度計、回流冷卻管、滴液漏 斗和氮導入管的1000ml燒瓶中投入丙二醇單甲基醚乙酸酯400份、AIBN 7份、甲基丙烯酸苄酯(化學式3)45份、甲基丙烯酸三環癸酯(化學式4)58份、甲基丙烯酸酯20份、甲基丙烯酸32份，進行氮置換。然後攪拌，使反應液的溫度上升到120℃，上升後反應20小時。這樣合成的鹼可溶性樹脂的最終固體成分為31.0%，固體成分的酸值為95mgKOH/g，通過GPC測定的重均分子量為35,000(表1)。 With agitator, thermometer, reflux cooling tube, drip leakage 400 parts of propylene glycol monomethyl ether acetate, 7 parts of AIBN, 45 parts of benzyl methacrylate (chemical formula 3), and 58 parts of tricyclodecyl methacrylate (chemical formula 4) were placed in a 1000 ml flask of a pipe and a nitrogen introduction tube. 20 parts of methacrylate and 32 parts of methacrylic acid were subjected to nitrogen substitution. Then, the temperature of the reaction liquid was raised to 120 ° C with stirring, and the reaction was carried out for 20 hours. The alkali-soluble resin thus synthesized had a final solid content of 31.0%, an acid value of a solid component of 95 mgKOH/g, and a weight average molecular weight measured by GPC of 35,000 (Table 1).

合成例7. A-7的合成Synthesis Example 7. Synthesis of A-7

在具備攪拌器、溫度計、回流冷卻管、滴液漏斗和氮導入管的1000ml燒瓶中投入丙二醇單甲基醚乙酸酯400份、AIBN 7份、甲基丙烯酸苄酯(化學式3)45份、甲基丙烯酸三環癸酯(化學式4)58份、甲基丙烯酸酯20份、甲基丙烯酸34份，進行氮置換。然後攪拌，使反應液的溫度上升到120℃，上升後反應20小時。這樣合成的鹼可溶性樹脂的最終固體成分為31.0%，固體成分的酸值為115mgKOH/g，通過GPC測定的重均分子量為35,000(表1)。 400 parts of propylene glycol monomethyl ether acetate, 7 parts of AIBN, and 45 parts of benzyl methacrylate (chemical formula 3) were placed in a 1000 ml flask equipped with a stirrer, a thermometer, a reflux cooling tube, a dropping funnel, and a nitrogen introduction tube. 58 parts of tricyclodecyl methacrylate (chemical formula 4), 20 parts of methacrylate, and 34 parts of methacrylic acid were subjected to nitrogen substitution. Then, the temperature of the reaction liquid was raised to 120 ° C with stirring, and the reaction was carried out for 20 hours. The alkali-soluble resin thus synthesized had a final solid content of 31.0%, an acid value of a solid component of 115 mgKOH/g, and a weight average molecular weight measured by GPC of 35,000 (Table 1).

合成例8. A-8的合成Synthesis Example 8. Synthesis of A-8

在具備攪拌器、溫度計、回流冷卻管、滴液漏斗和氮導入管的1000ml燒瓶中投入丙二醇單甲基醚乙酸酯400份、AIBN 7份、甲基丙烯酸苄酯(化學式3)45份、甲基丙烯酸三環癸酯(化學式4)58份、甲基丙烯酸酯20份、甲基丙烯酸34份，進行氮置換。然 後攪拌，使反應液的溫度上升到120℃，上升後反應15小時。這樣合成的鹼可溶性樹脂的最終固體成分為31.0%，固體成分的酸值為115mgKOH/g，通過GPC測定的重均分子量為27,000(表1)。 400 parts of propylene glycol monomethyl ether acetate, 7 parts of AIBN, and 45 parts of benzyl methacrylate (chemical formula 3) were placed in a 1000 ml flask equipped with a stirrer, a thermometer, a reflux cooling tube, a dropping funnel, and a nitrogen introduction tube. 58 parts of tricyclodecyl methacrylate (chemical formula 4), 20 parts of methacrylate, and 34 parts of methacrylic acid were subjected to nitrogen substitution. Of course After stirring, the temperature of the reaction liquid was raised to 120 ° C, and the reaction was raised for 15 hours. The alkali-soluble resin thus synthesized had a final solid content of 31.0%, an acid value of a solid component of 115 mgKOH/g, and a weight average molecular weight measured by GPC of 27,000 (Table 1).

實施例1. 著色感光性樹脂組合物的製造Example 1. Production of Colored Photosensitive Resin Composition

將C.I.顏料綠58(顏料)12份、C.I.顏料黃150(顏料)1.8份、作為顏料分散劑的BYK-2001 4.0份、丙二醇單甲基醚乙酸酯82.2份混合，使用珠磨機使顏料充分地分散，接下來，將合成例1的鹼可溶性樹脂A-1 30份、聚合性化合物A9550 6.6份、作為肟酯系引發劑的PBG-305(製造公司：TRONLY)1.3份、丙二醇單甲基醚乙酸酯52.7份混合，得到了著色感光性樹脂組合物。 12 parts of CI Pigment Green 58 (pigment), 1.8 parts of CI Pigment Yellow 150 (pigment), BYK-2001 4.0 parts as a pigment dispersant, and 82.2 parts of propylene glycol monomethyl ether acetate were mixed, and a bead mill was used to make the pigment. After sufficiently dispersing, 30 parts of the alkali-soluble resin A-1 of Synthesis Example 1, 6.6 parts of the polymerizable compound A9550, and 1.3 parts of PBG-305 (manufacturing company: TRONLY) as an oxime ester-based initiator, propylene glycol monomethyl 52.7 parts of a base ether acetate was mixed, and the colored photosensitive resin composition was obtained.

實施例2. 著色感光性樹脂組合物的製造Example 2. Production of Colored Photosensitive Resin Composition

除了將實施例1的鹼可溶性樹脂替代為合成例2 的A-2以外，採用同一組成，得到了著色感光性樹脂組合物。 Substituting the alkali-soluble resin of Example 1 for Synthesis Example 2 In the same manner as in A-2, the same composition was used to obtain a colored photosensitive resin composition.

比較例1. 著色感光性樹脂組合物的製造Comparative Example 1. Production of Colored Photosensitive Resin Composition

除了將實施例1的鹼可溶性樹脂替代為合成例3的A-3以外，採用同一組成，得到了著色感光性樹脂組合物。 A colored photosensitive resin composition was obtained by using the same composition except that the alkali-soluble resin of Example 1 was replaced by A-3 of Synthesis Example 3.

比較例2. 著色感光性樹脂組合物的製造Comparative Example 2. Production of Colored Photosensitive Resin Composition

除了將實施例1的鹼可溶性樹脂替代為合成例4的A-4以外，採用同一組成，得到了著色感光性樹脂組合物。 A colored photosensitive resin composition was obtained by using the same composition except that the alkali-soluble resin of Example 1 was replaced by A-4 of Synthesis Example 4.

比較例3. 著色感光性樹脂組合物的製造Comparative Example 3. Production of Colored Photosensitive Resin Composition

除了將實施例1的鹼可溶性樹脂替代為合成例5的A-5以外，採用同一組成，得到了著色感光性樹脂組合物。 A coloring photosensitive resin composition was obtained by using the same composition except that the alkali-soluble resin of Example 1 was replaced by A-5 of Synthesis Example 5.

比較例4. 著色感光性樹脂組合物的製造Comparative Example 4. Production of Colored Photosensitive Resin Composition

除了將實施例1的鹼可溶性樹脂替代為合成例6的A-6以外，採用同一組成，得到了著色感光性樹脂組合物。 The same composition was used except that the alkali-soluble resin of Example 1 was replaced by A-6 of Synthesis Example 6, and a colored photosensitive resin composition was obtained.

比較例5. 著色感光性樹脂組合物的製造Comparative Example 5. Production of Colored Photosensitive Resin Composition

除了將實施例1的鹼可溶性樹脂替代為合成例7的A-7以外，採用同一組成，得到了著色感光性樹脂組合物。 A colored photosensitive resin composition was obtained by using the same composition except that the alkali-soluble resin of Example 1 was replaced by A-7 of Synthesis Example 7.

比較例6. 著色感光性樹脂組合物的製造Comparative Example 6. Production of Colored Photosensitive Resin Composition

除了將實施例1的鹼可溶性樹脂替代為合成例8 的A-8以外，採用同一組成，得到了著色感光性樹脂組合物。 Substituting the alkali-soluble resin of Example 1 for Synthesis Example 8 Other than A-8, the same composition was used to obtain a colored photosensitive resin composition.

實驗例Experimental example

使用上述實施例1~2和比較例1~6中製造的著色感光性樹脂組合物製造濾色器。 A color filter was produced using the colored photosensitive resin compositions produced in the above Examples 1 to 2 and Comparative Examples 1 to 6.

具體地，採用旋塗法將上述各個感光性樹脂組合物塗布到BM基板上後，放置到加熱板上，在100℃的溫度下維持2分鐘，形成了薄膜。接下來，在上述薄膜上放置具有使透射率在1~100%的範圍內階梯狀變化的圖案和1μm~100μm的線/空間圖案的試驗光掩模，使與試驗光掩模的間隔為200μm，照射紫外線。此時，紫外線光源使用包含g、h、i線全部的1KW的高壓汞燈，以50mJ/cm2的照度照射，沒有使用特別的光學濾波器。將上述紫外線照射過的薄膜浸漬於pH10.5的KOH水溶液顯影溶液中2分鐘，使其顯影。後工序烘焙(bake)在230℃下進行20分鐘。上述製造的濾色器的膜厚度為2.5μm。 Specifically, each of the above-mentioned photosensitive resin compositions was applied onto a BM substrate by a spin coating method, placed on a hot plate, and maintained at a temperature of 100 ° C for 2 minutes to form a film. Next, a test photomask having a pattern in which the transmittance is changed stepwise in the range of 1 to 100% and a line/space pattern of 1 μm to 100 μm is placed on the film so that the interval from the test photomask is 200 μm. , irradiated with ultraviolet light. At this time, the ultraviolet light source was irradiated with an illuminance of 50 mJ/cm 2 using a high-pressure mercury lamp of 1 kW including all of the g, h, and i lines, and no special optical filter was used. The ultraviolet ray-irradiated film was immersed in a KOH aqueous solution developing solution having a pH of 10.5 for 2 minutes to be developed. The post-process bake was carried out at 230 ° C for 20 minutes. The color filter manufactured above had a film thickness of 2.5 μm.

<密合性> <adhesion>

對於上述製作的濾色器，使用Nikon社製造的ECLIPSE LV100POL Model的光學顯微鏡，以反射模式確認1μm~100μm的圖案有無消失，用殘留的圖案標準(殘留的圖案的尺寸越小，為密合性越優異的製品)評價密合性，將其結果示於表2中。 For the color filter prepared as described above, an optical microscope of the ECLIPSE LV100 POL model manufactured by Nikon Co., Ltd. was used to confirm the presence or absence of the pattern of 1 μm to 100 μm in the reflection mode, and the residual pattern standard was used (the smaller the size of the remaining pattern, the adhesion was obtained). The more excellent the product) was evaluated for adhesion, and the results are shown in Table 2.

<剝離(peeling)> <peeling>

在上述製作的濾色器製作過程中，旋塗時使用採用了UV清洗(700mj)的BM基板，實施了感光性樹脂組合物的塗布。以後，對於製作的濾色器，使用Nikon社製造的ECLIPSE LV100POL Model的光學顯微鏡，以反射模式確認了剝離。 In the production process of the color filter produced above, the BM substrate using UV cleaning (700 mj) was used for spin coating, and the photosensitive resin composition was applied. In the future, the optical filter of the ECLIPSE LV100POL Model manufactured by Nikon Co., Ltd. was used for the color filter, and the peeling was confirmed in the reflection mode.

剝離特性的判斷標準為：將圖1那樣的水準時作為基準，判斷為O、X，將其結果示於表2。 The criteria for judging the peeling property were as follows: The level of time as shown in Fig. 1 was used as a reference, and it was judged as O and X, and the results are shown in Table 2.

如表2中所示那樣，在實施例1和2的著色感光性樹脂組合物的情況下，與比較例1~6相比，在密合性和剝離特性的方面顯示出優異的結果。 As shown in Table 2, in the case of the colored photosensitive resin compositions of Examples 1 and 2, excellent results were obtained in terms of adhesion and peeling characteristics as compared with Comparative Examples 1 to 6.

Claims (5)

一種著色感光性樹脂組合物，其包含著色劑、鹼可溶性樹脂、光聚合性化合物、光聚合引發劑、和溶劑，其特徵在於，該鹼可溶性樹脂包含由下述化學式1表示的化合物和由下述化學式2表示的化合物，該鹼可溶性樹脂的重均分子量為25,000~32,000，該鹼可溶性樹脂的酸值為50~100mgKOH/g： 上述化學式1中，R1各自獨立地為氫或碳數1~5的烷基， 上述化學式2中，R2各自獨立地為氫或碳數1~5的烷基。 A colored photosensitive resin composition comprising a coloring agent, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent, wherein the alkali-soluble resin contains a compound represented by the following Chemical Formula 1 and The compound represented by Chemical Formula 2 has a weight average molecular weight of 25,000 to 32,000 and an acid value of the alkali-soluble resin of 50 to 100 mgKOH/g: In the above Chemical Formula 1, R1 is each independently hydrogen or an alkyl group having 1 to 5 carbon atoms. In the above Chemical Formula 2, R2 is each independently hydrogen or an alkyl group having 1 to 5 carbon atoms. 如請求項1之著色感光性樹脂組合物，其中，該著色劑包含1種以上的綠色顏料或綠色染料。 The colored photosensitive resin composition of claim 1, wherein the coloring agent contains one or more kinds of green pigments or green dyes. 如請求項1之著色感光性樹脂組合物，其中，該鹼可溶性樹脂包含由下述化學式3表示的化合物和由下述化學式4表示的化合物： The colored photosensitive resin composition of claim 1, wherein the alkali-soluble resin comprises a compound represented by the following Chemical Formula 3 and a compound represented by the following Chemical Formula 4: 如請求項1之著色感光性樹脂組合物，其中，以著色感光性樹脂組合物的固體成分總重量為基準，含有5~60重量%的該著色劑，含有10~80重量%的該鹼可溶性樹脂，含有5~50重量%的該光聚合性化合物，以鹼可溶性樹脂和光聚合性化合物的固體成分總重量為基準，含有0.1~40重量 %的該光聚合引發劑，以著色感光性樹脂組合物的總重量為基準，含有60~90重量%的該溶劑。 The colored photosensitive resin composition of claim 1, which contains 5 to 60% by weight of the coloring agent based on the total weight of the solid content of the colored photosensitive resin composition, and contains 10 to 80% by weight of the alkali soluble The resin contains 5 to 50% by weight of the photopolymerizable compound, and contains 0.1 to 40% by weight based on the total weight of the solid content of the alkali-soluble resin and the photopolymerizable compound. The photopolymerization initiator of % contains 60 to 90% by weight of the solvent based on the total weight of the colored photosensitive resin composition. 一種濾色器，係使用如請求項1至4中任一項之著色感光性樹脂組合物而製造。 A color filter produced by using the colored photosensitive resin composition according to any one of claims 1 to 4.
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CN106483762A (en) 2017-03-08
KR102069143B1 (en) 2020-01-22

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