TW201638669A - Colored photosensitive resin composition, color filter and liquid crystal display device including the color filter - Google Patents

Colored photosensitive resin composition, color filter and liquid crystal display device including the color filter Download PDF

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TW201638669A
TW201638669A TW105105438A TW105105438A TW201638669A TW 201638669 A TW201638669 A TW 201638669A TW 105105438 A TW105105438 A TW 105105438A TW 105105438 A TW105105438 A TW 105105438A TW 201638669 A TW201638669 A TW 201638669A
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weight
anhydride
chemical formula
resin composition
photosensitive resin
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TW105105438A
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Chinese (zh)
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權鳳壹
裵辰哲
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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
    • G03F7/004—Photosensitive materials
    • G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • 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
    • 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
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials For Photolithography (AREA)
  • Optical Filters (AREA)

Abstract

The present invention provides a colored photosensitive resin composition including a coloring agent (A), an alkali-soluble resin (B), a photopolymerizable compound (C), a photopolymerization initiator (D) and a solvent (E), wherein the coloring agent (A) includes a dye, and the alkali-soluble resin (B) includes compounds represented by the following Chemical Formula 1 and Chemical Formula 2 and has a glass transition temperature of lower than 0 DEG C, a color filter, and a liquid crystal display device including the color filter.

Description

著色感光樹脂組合物、彩色濾光片和液晶顯示裝置 Colored photosensitive resin composition, color filter, and liquid crystal display device 發明領域 Field of invention

本發明涉及著色感光樹脂組合物，利用該著色感光樹脂組合物製造的彩色濾光片，和包含所述彩色濾光片的液晶顯示裝置。 The present invention relates to a colored photosensitive resin composition, a color filter produced using the colored photosensitive resin composition, and a liquid crystal display device including the color filter.

發明背景 Background of the invention

顯示器的尺寸在快步增長，並且對具有高色彩再現能力的高品質顯示器的需求在增長。屏面的電力消耗量隨著尺寸增加而增加，為求高色彩再現能力，著色材料的含量和用於製造彩色濾光片的著色感光樹脂組合物的膜厚度不斷增加。另外，為了通過光效率提高來改善能量效率，一直在進行對彩色濾光片的高穿透度的開發。然而，在現有的顏料分散系統中，顏料的霧化達到一個限度，目前，正在研究將顏料和染料一起作為著色劑使用的方法。然而，當使用包含染料作為著色劑的著色感光樹脂組合物製造彩色濾光片時，顯影速率低並且敏感度不足，在利用鹼性顯影溶液顯影的過程中發生所形成的圖案脫離。 The size of displays is growing at a rapid pace, and the demand for high quality displays with high color reproduction capabilities is growing. The power consumption of the panel increases as the size increases, and the film thickness of the coloring photosensitive resin composition for producing a color filter is continuously increased in order to achieve high color reproduction ability. In addition, in order to improve energy efficiency by improving light efficiency, development of high transparency of color filters has been progressing. However, in the existing pigment dispersion system, the atomization of the pigment reaches a limit, and at present, a method of using a pigment together with a dye as a colorant is being studied. However, when a color filter is produced using a colored photosensitive resin composition containing a dye as a colorant, the development rate is low and the sensitivity is insufficient, and the formed pattern is detached during development with an alkali developing solution.

在這方面，韓國專利申請公佈No.2012-0080123公開了著色感光組合物、製造彩色濾光片的方法、彩色濾光片、液晶顯示裝置、和有機EL顯示裝置，沒有提出對上述問題的可替選方案。 In this regard, the Korean Patent Application Publication No. 2012-0080123 discloses a coloring photosensitive composition, a method of manufacturing a color filter, a color filter, a liquid crystal display device, and an organic EL display device, and the above problems are not proposed. Alternative.

【現有技術文獻】 [Prior Art Literature]

【專利文獻】 [Patent Literature]

(專利文獻1)韓國專利申請特許公佈No.2012-0080123 (Patent Document 1) Korean Patent Application Patent Publication No. 2012-0080123

發明概要 Summary of invention

本發明的目的是提供著色感光樹脂組合物，其即使在很高的顯影速率下仍表現出優異的黏合性、具有高透射率和優異的耐熱性，因此適合於製造高品質彩色濾光片。 An object of the present invention is to provide a colored photosensitive resin composition which exhibits excellent adhesion, high transmittance, and excellent heat resistance even at a high development rate, and is therefore suitable for producing a high quality color filter.

本發明的另一個目的是提供利用所述著色感光樹脂組合物製造的彩色濾光片。 Another object of the present invention is to provide a color filter manufactured using the colored photosensitive resin composition.

本發明的又一個目的是提供配備了本發明的彩色濾光片的液晶顯示裝置。 It is still another object of the present invention to provide a liquid crystal display device equipped with the color filter of the present invention.

鑒於上述，本發明的一個方面提供了著色感光樹脂組合物，其包含著色劑(A)、鹼溶性樹脂(B)、光可聚合性化合物(C)、光聚合引發劑(D)和溶劑(E)，其中所述著色劑(A)包含染料，並且所述鹼溶性樹脂(B)包含由下面化學式1和化學式2表示的化合物並具有低於0℃的玻璃化轉變溫度。 In view of the above, an aspect of the 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) wherein the colorant (A) contains a dye, and the alkali-soluble resin (B) contains a compound represented by the following Chemical Formula 1 and Chemical Formula 2 and has a glass transition temperature lower than 0 °C.

本發明的另一個方面提供了利用所述著色感光 樹脂組合物製造的彩色濾光片。 Another aspect of the invention provides for utilizing the coloring sensitization A color filter made of a resin composition.

本發明的又一個方面提供了包含所述彩色濾光片的液晶顯示裝置。 Yet another aspect of the present invention provides a liquid crystal display device including the color filter.

較佳實施例之詳細說明 Detailed description of the preferred embodiment

本發明涉及著色感光樹脂組合物，其包含著色劑(A)、鹼溶性樹脂(B)、光可聚合性化合物(C)、光聚合引發劑(D)和溶劑(E)，其中所述鹼溶性樹脂(B)具有低於0℃的玻璃化轉變溫度。本發明的感光樹脂組合物通過包含特定的鹼溶性樹脂(B)，即使在很高的顯影速率下仍表現出優異的黏合性。另外，本發明的著色感光樹脂組合物具有高透射率和優異的耐熱性，因此，具有適合於製造高品質彩色濾光片的優點。 The present invention relates to 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), wherein the base The soluble resin (B) has a glass transition temperature of less than 0 °C. The photosensitive resin composition of the present invention exhibits excellent adhesion even at a high development rate by containing a specific alkali-soluble resin (B). Further, the colored photosensitive resin composition of the present invention has high transmittance and excellent heat resistance, and therefore has an advantage suitable for producing a high-quality color filter.

在下文中，將通過每種成分詳細地描述本發明。 Hereinafter, the present invention will be described in detail by each component.

著色劑(A)Colorant (A)

著色劑(A)具有一種或多種類型的染料(a1)作為主要組分，並可以包含著色劑顏料(a2)。 The colorant (A) has one or more types of dyes (a1) as a main component, and may contain a colorant pigment (a2).

每種成分描述如下。 Each component is described below.

染料(a1)Dye (a1)

所述染料可以沒有限制地使用，只要它具有對有機溶劑的溶解性即可。優選地，可以使用能夠確保可靠性例如對鹼性顯影溶液的溶解性、耐熱性和耐溶劑性同時具 有對有機溶劑的溶解性的染料。 The dye can be used without limitation as long as it has solubility in an organic solvent. Preferably, it is possible to use a property capable of ensuring reliability such as solubility to an alkali developing solution, heat resistance and solvent resistance. A dye having solubility in an organic solvent.

作為所述染料，可以使用選自具有酸性基團例如磺酸或羧酸的酸性染料、酸性染料與含氮化合物的鹽、酸性染料的磺醯胺等、及其衍生物的那些染料，並且除這些之外，也可以選擇偶氮類、氧雜蒽類或酞菁類酸性染料，及其衍生物。所述染料優選包括在色指數(由染色家協會(Society of Dyers and Colourists)出版)中歸類為染料的化合物或在染色說明(Dye Note)(色染公司(Color and Dye Corporation))中所描述的已知染料。 As the dye, those selected from 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 derivatives thereof can be used, and In addition to these, azo, oxonium or phthalocyanine acid dyes, and derivatives thereof, may also be selected. The dye preferably comprises a compound classified as a dye in a color index (published by the Society of Dyers and Colourists) or in Dye Note (Color and Dye Corporation). A known dye is described.

作為C.I.溶劑染料，所述染料的具體例子包括，紅色染料例如C.I.溶劑紅8、45、49、89、111、122、125、130、132，146和179；藍色染料例如C.I.溶劑藍5、35、36、37、44、59、67和70；紫色染料例如C.I.溶劑紫8、9、13、14、36、37、47和49；黃色染料例如C.I.溶劑黃4、14、15、23、24、38、62、63、68、82、94、98、99和162；橙色染料例如C.I.溶劑橙2、7、11、15、26和56；和綠色染料例如C.I.溶劑綠1、3、4、5、7、28、29、32、33、34和35。 As the CI solvent dye, specific examples of the dye include red dyes such as CI solvent red 8, 45, 49, 89, 111, 122, 125, 130, 132, 146 and 179; blue dyes such as CI solvent blue 5, 35, 36, 37, 44, 59, 67 and 70; purple dyes such as CI solvent violet 8, 9, 13, 14, 36, 37, 47 and 49; yellow dyes such as CI solvent yellow 4, 14, 15, 23, 24, 38, 62, 63, 68, 82, 94, 98, 99 and 162; orange dyes such as CI Solvent Orange 2, 7, 11, 15, 26 and 56; and green dyes such as CI Solvent Green 1, 3, 4 , 5, 7, 28, 29, 32, 33, 34, and 35.

在C.I.溶劑染料之中，優選具有優異的有機溶劑溶解性的C.I.溶劑紅8、49、89、111、122、132、146和179；C.I.溶劑藍35、36、44、45和70；和C.I.溶劑紫13，並且在 這些之中，更優選C.I.溶劑紅8、122和132。 Among the CI solvent dyes, CI Solvent Red 8, 49, 89, 111, 122, 132, 146 and 179 having excellent solubility in organic solvents are preferred; CI Solvent Blue 35, 36, 44, 45 and 70; and CI Solvent violet 13, and at Among these, C.I. Solvent Red 8, 122 and 132 are more preferable.

另外，作為C.I.酸性染料，具體例子可以包括紅色染料例如C.I.酸性紅1、4、8、14、17、18、26、27、29、31、34、35、37、42、44、50、51、52、57、66、73、80、87、88、91、92、94、97、103、111、114、129、133、134、138、143、145、150、151、158、176、182、183、198、206、211、215、216、217、227、228、249、252、257、258、260、261、266、268、270、274、277、280、281、195、308、312、315、316、339、341、345、346、349、382、383、394、401、412、417、418、422和426；黃色染料例如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和251；橙色染料例如C.I.酸性橙6、7、8、10、12、26、50、51、52、56、62、63、64、74、75、94、95、107、108、169和173；藍色染料例如C.I.酸性藍1、7、9、15、18、23、25、27、29、40、42、45、51、62、70、74、80、83、86、87、90、92、96、103、112、113、120、129、138、147、150、 158、171、182、192、210、242、243、256、259、267、278、280、285、290、296、315、324：1、335和340；紫色染料例如C.I.酸性紫6B、7、9、17、19和66；綠色染料例如C.I.酸性綠1、3、5、9、16、25、27、50、58、63、65、80、104、105、106和109等。 Further, as the CI acid dye, specific examples may include red dyes such as CI acid red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 34, 35, 37, 42, 44, 50, 51 , 52, 57, 66, 73, 80, 87, 88, 91, 92, 94, 97, 103, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 158, 176, 182 , 183, 198, 206, 211, 215, 216, 217, 227, 228, 249, 252, 257, 258, 260, 261, 266, 268, 270, 274, 277, 280, 281, 195, 308, 312 , 315, 316, 339, 341, 345, 346, 349, 382, 383, 394, 401, 412, 417, 418, 422 and 426; yellow dyes such as 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, 240, 242, 243, and 251; orange For example, CI Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 169 and 173; blue dye For example, CI Acid Blue 1, 7, 9, 15, 18, 23, 25, 27, 29, 40, 42, 45, 51, 62, 70, 74, 80, 83, 86, 87, 90, 92, 96, 103, 112, 113, 120, 129, 138, 147, 150, 158, 171, 182, 192, 210, 242, 243, 256, 259, 267, 278, 280, 285, 290, 296, 315, 324: 1, 335 and 340; purple dyes such as CI Acid Violet 6B, 7, 9, 17, 19 and 66; green dyes such as CI Acid Green 1, 3, 5, 9, 16, 25, 27, 50, 58, 63, 65, 80, 104, 105, 106 and 109 and the like.

在所述酸性染料之中，優選具有優異的有機溶劑溶解性的C.I.酸性紅92；C.I.酸性藍80和90；和C.I.酸性紫66。 Among the acid dyes, C.I. Acid Red 92 having excellent organic solvent solubility; C.I. Acid Blue 80 and 90; and C.I. Acid Violet 66 are preferred.

此外，作為C.I.直接染料，具體例子可以包括紅色染料例如C.I.直接紅79、82、83、84、91、92、96、97、98、99、105、106、107、172、173、176、177、179、181、182、184、204、207、211、213、218、220、221、222、232、233、234、241、243、246和250；黃色染料例如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和141；橙色染料例如C.I.直接橙34、39、41、46、50、52、56、57、61、64、65、68、70、96、97、106和107；藍色染料例如C.I.直接藍38、44、57、70、77、80、81、84、85、86、90、93、94、95、97、98、99、100、101、106、107、108、109、113、114、115、117、119、137、149、150、153、155、156、158、159、160、161、162、163、164、166、167、170、171、172、173、188、189、190、192、193、194、196、198、199、200、207、209、 210、212、213、214、222、228、229、237、238、242、243、244、245、247、248、250、251、252、256、257、259、260、268、274、275和293；紫色染料例如C.I.直接紫47、52、54、59、60、65、66、79、80、81、82、84、89、90、93、95、96、103和104；綠色染料例如C.I.直接綠25、27、31、32、34、37、63、65、66、67、68、69、72、77、79和82等。 Further, as the CI direct dye, specific examples may include red dyes such as CI Direct Red 79, 82, 83, 84, 91, 92, 96, 97, 98, 99, 105, 106, 107, 172, 173, 176, 177. , 179, 181, 182, 184, 204, 207, 211, 213, 218, 220, 221, 222, 232, 233, 234, 241, 243, 246 and 250; yellow dyes such as CI Direct Yellow 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 and 141; orange Dyes such as CI Direct Orange 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106 and 107; blue dyes such as CI Direct Blue 38, 44, 57, 70, 77, 80, 81, 84, 85, 86, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 108, 109, 113, 114, 115, 117, 119, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 166, 167, 170, 171, 172, 173, 188, 189, 190, 192, 193, 194, 196, 198, 199, 200, 207, 209, 210,212,213,214,222,228,229,237,238,242,243,244,245,247,248,250,251,252,256,257,259, 293; violet dyes such as CI Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103 and 104; green dyes such as CI Directly green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79 and 82, and the like.

可以包含黃色染料例如C.I.媒染黃5、8、10、16、20、26、30、31、33、42、43、45、56、61、62和65；紅色染料例如C.I.媒染紅1、2、3、4、9、11、12、14、17、18、19、22、23、24、25、26、30、32、33、36、37、38、39、41、43、45、46、48、53、56、63、71、74、85、86、88、90、94和95；橙色染料例如C.I.媒染橙3、4、5、8、12、13、14、20、21、23、24、28、29、32、34、35、36、37、42、43、47和48；藍色染料例如C.I.媒染藍1、2、3、7、8、9、12、13、15、16、19、20、21、22、23、24、26、30、31、32、39、40、41、43、44、48、49、53、61、74、77、83和84；紫色染料例如C.I.媒染紫1、2、4、5、7、14、22、24、30、31、32、37、40、41、44、45、47、48、53和58；綠色染料例如C.I.媒染綠1、3、4、5、10、15、19、26、29、33、34、35、41、43和53等。 May contain yellow dyes such as CI mordant yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62 and 65; red dyes such as CI mordant red 1, 2 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 30, 32, 33, 36, 37, 38, 39, 41, 43, 45, 46, 48, 53, 56, 63, 71, 74, 85, 86, 88, 90, 94 and 95; orange dyes such as CI mord orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47 and 48; blue dyes such as CI mordant blue 1, 2, 3, 7, 8, 9, 12, 13, 15, 16 , 19, 20, 21, 22, 23, 24, 26, 30, 31, 32, 39, 40, 41, 43, 44, 48, 49, 53, 61, 74, 77, 83 and 84; CI mordant violet 1, 2, 4, 5, 7, 14, 22, 24, 30, 31, 32, 37, 40, 41, 44, 45, 47, 48, 53 and 58; green dyes such as CI mord green 1 , 3, 4, 5, 10, 15, 19, 26, 29, 33, 34, 35, 41, 43 and 53 and so on.

所述染料可以單獨或作為兩種或更多種類的組 合使用。 The dyes may be used alone or as a group of two or more species Used together.

顏料(a2)Pigment (a2)

作為顏料，可以使用本領域中通常使用的有機顏料或無機顏料。可以使用用於印刷墨水、噴墨墨水等中的各種各樣的顏料作為有機顏料，並且其具體例子包括水溶性偶氮顏料、不溶性偶氮顏料、酞菁顏料、喹吖酮顏料、異二氫吲哚酮(isoindolidone)顏料、異吲哚啉顏料、苝顏料、苝酮顏料、二噁嗪顏料、蒽醌顏料、二蒽醌基(dianthraquinonyl)顏料、蒽嘧啶(anthrapyrimidine)顏料、蒽嵌蒽醌顏料、靛蒽醌顏料、黃烷士酮顏料、皮蒽酮顏料、吡咯并吡咯二酮(diketopyrrolopyrrole)顏料等等。作為無機顏料，可以包括金屬化合物例如金屬氧化物或金屬絡合物鹽，其具體例子可以包括金屬例如鐵、鈷、鋁、鎘、鉛、銅、鈦、鎂、鉻、鋅、銻和炭黑的氧化物、複合金屬氧化物等。特別是，作為所述有機顏料和無機顏料，可以包括在色指數(由染色家協會(Society of Dyers and Colourists)出版)中歸類為顏料的化合物，更具體地是，下列色指數(C.I.)編號的顏料，然而，所述顏料不限於此。 As the pigment, an organic pigment or an inorganic pigment which is generally used in the art can be used. Various pigments used in printing inks, inkjet inks, and the like can be used as the organic pigment, and specific examples thereof include water-soluble azo pigments, insoluble azo pigments, phthalocyanine pigments, quinophthalone pigments, iso-dihydrogen Isoindolidone pigment, isoporphyrin pigment, anthraquinone pigment, anthrone pigment, dioxazine pigment, anthraquinone pigment, dianthraquinonyl pigment, anthrapyrimidine pigment, anthraquinone Pigments, anthraquinone pigments, flavanone pigments, dermatone pigments, pyrrolopyrrolone (diketopyrrolopyrrole) pigments, and the like. As the inorganic pigment, a metal compound such as a metal oxide or a metal complex salt may be included, and specific examples thereof may include metals such as iron, cobalt, aluminum, cadmium, lead, copper, titanium, magnesium, chromium, zinc, bismuth, and carbon black. Oxides, composite metal oxides, and the like. In particular, as the organic pigment and the inorganic pigment, a compound classified as a pigment in a color index (published by the Society of Dyers and Colourists), more specifically, the following color index (CI) may be included. Numbered pigments, however, the pigments are not 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；C.I.顏料橙13、31、36、38、40、42、43、51、55、59、61、64、65、和71；C.I.顏料紅9、97、105、122、123、144、149、166、 168、176、177、180、192、208、215、216、224、242、254、255和264；C.I.顏料紫14、19、23、29、32、33、36、37和38；C.I.顏料藍15(15：3、15：4、15：6等)、21、28、60、64和76；C.I.顏料綠7、10、15、25、36、47和58；C.I顏料棕28；C.I顏料黑1和7；等等。 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; CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, and 71; CI Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 208, 215, 216, 224, 242, 254, 255 and 264; CI Pigment Violet 14, 19, 23, 29, 32, 33, 36, 37 and 38; CI Pigment Blue 15 (15:3, 15:4, 15:6, etc.), 21, 28, 60, 64 and 76; CI Pigment Green 7, 10, 15, 25, 36, 47 and 58; CI Pigment Brown 28; CI Pigment Black 1 and 7; and so on.

所述顏料(a2)可以單獨或作為兩種或更多種類的組合使用。 The pigment (a2) may be used singly or in combination of two or more kinds.

在上面說明的C.I.顏料之中，可以優選使用選自下列的顏料：C.I.顏料橙38、C.I.顏料紅122、C.I.顏料紅166、C.I.顏料紅177、C.I.顏料紅208、C.I.顏料紅242、C.I.顏料紅254、C.I.顏料紅255、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、C.I.顏料紫23、C.I.顏料藍15：3和顏料藍15：6。 Among the CI pigments described above, a pigment selected from the group consisting of CI Pigment Orange 38, CI Pigment Red 122, CI Pigment Red 166, CI Pigment Red 177, CI Pigment Red 208, CI Pigment Red 242, CI Pigment can be preferably used. Red 254, CI Pigment Red 255, CI Pigment Yellow 138, CI Pigment Yellow 139, CI Pigment Yellow 150, CI Pigment Yellow 185, CI Pigment Green 7, CI Pigment Green 36, CI Pigment Green 58, CI Pigment Violet 23, CI Pigment Blue 15:3 and Pigment Blue 15:6.

所述顏料優選使用顏料粒子均勻分散在其中的顏料分散液。均勻分散顏料粒子的方法的一個例子包括含有顏料分散劑(a3)的分散方法，並且使用這種方法，可以得到顏料均勻分散在溶液中的顏料分散液。 The pigment preferably uses a pigment dispersion in which pigment particles are uniformly dispersed. One example of the method of uniformly dispersing the pigment particles includes a dispersion method containing the pigment dispersant (a3), and with this method, a pigment dispersion in which the pigment is uniformly dispersed in a solution can be obtained.

顏料分散劑的具體例子可以包括陽離子基、陰離子基、非離子基、兩性、聚酯基、多胺基等的表面活性劑等，並且這些可以單獨或作為兩種或更多種類型的組合使 用。 Specific examples of the pigment dispersant may include a cationic group, an anionic group, a nonionic group, an amphoteric, a polyester group, a polyamine group, or the like, and the like, and these may be used singly or as a combination of two or more types. use.

相對於所述顏料分散組合物的總固體以重量分數計，顏料(a2)的含量是20重量%至90重量%並優選30重量%至70重量%。所述顏料含量基於上述標準在20重量%至90重量%範圍內是優選的，因為黏度低、儲存穩定性優異和分散效率高，其在對比度範圍增加中是有效的。 The content of the pigment (a2) is from 20% by weight to 90% by weight and preferably from 30% by weight to 70% by weight based on the total solids of the pigment dispersion composition. The pigment content is preferably in the range of 20% by weight to 90% by weight based on the above criteria, and is excellent in the range of contrast because of low viscosity, excellent storage stability, and high dispersion efficiency.

除了以上提到的丙烯酸類分散劑之外，所述分散劑(a3)還可以使用其他樹脂型顏料分散劑。所述其他樹脂型顏料分散劑的例子可以包括已知的樹脂型顏料分散劑，特別是油性分散劑例如聚氨酯、由聚丙烯酸酯代表的聚羧酸酯、不飽和聚醯胺、多羧酸、多羧酸的(部分)胺鹽、多羧酸的銨鹽、多羧酸的烷基胺鹽、聚矽氧烷、長鏈聚氨基醯胺磷酸鹽、含羥基的多羧酸酯及其改性產物、或從具有自由羧基的聚酯與聚(低級烷烯亞胺)反應形成的醯胺或其鹽；水溶性樹脂或水溶性聚合物化合物例如(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；聚酯；改性聚丙烯酸酯；環氧乙烷/環氧丙烷加合物；磷酸酯，等等。作為所述樹脂型分散劑的商品，所述陽離子基樹脂分散劑的例子可以包括BYK Chemie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和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和EFKA-4800；Lubrizol公司的商品名：SOLSPERS-24000、SOLSPERS-32550和NBZ-4204/10；Kawaken精細化工(Fine Chemicals)Co.,Ltd.的商品名：HINOACT T-6000、HINOACT T-7000和HINOACT T-8000；Ajinomoto Fine-Techno Co.,Inc.的商品名：AJISPER PB-821、AJISPER PB-822和AJISPER PB-823；Kyoeisha Chemical Co.,Ltd.的商品名：FLORENE DOPA-17HF、FLORENE DOPA-15BHF、FLORENE DOPA-33和FLORENE DOPA-44，等等。所述除丙烯酸類分散劑以外的其他樹脂型顏料分散劑可以單獨或作為兩種或更多種類型的組合使用，或可以與所述丙烯酸類分散劑一起使用。 In addition to the above-mentioned acrylic dispersant, the dispersant (a3) may also use other resin type pigment dispersants. Examples of the other resin type pigment dispersant may include known resin type pigment dispersants, particularly oily dispersants such as polyurethane, polycarboxylate represented by polyacrylate, unsaturated polyamine, 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 polyaminoguanamine phosphate, a hydroxyl group-containing polycarboxylate, and the like a product, or a guanamine or a salt thereof formed by reacting a polyester having a free carboxyl group with a poly(lower alkeneimine); a water-soluble resin or a water-soluble polymer compound such as a (meth)acrylic acid-styrene copolymer, (meth)acrylic acid-(meth)acrylate copolymer, styrene-maleic acid copolymer, polyvinyl alcohol or polyvinylpyrrolidone; polyester; modified polyacrylate; ethylene oxide/propylene oxide Adducts; phosphates, and the like. As a commercial product of the resin type dispersant, examples of the cationic resin dispersant may include BYK Chemie's trade names: DISPER BYK-160, DISPER BYK-161, DISPER BYK-162, DISPER BYK-163, DISPER BYK- 164, DISPER BYK-166, DISPER BYK-171, DISPER BYK-182 and 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 and EFKA-4800; Lubrizol's trade name: SOLSPERS-24000, SOLSPERS-32550 and NBZ-4204/10; trade names of Kawaken Fine Chemicals Co., Ltd.: HINOACT T-6000, HINOACT T-7000 and HINOACT T-8000; Ajinomoto Fine-Techno Co ., Inc. trade name: AJISPER PB-821, AJISPER PB-822 and AJISPER PB-823; Kyoeisha Chemical Co., Ltd. trade name: FLORENE DOPA-17HF, FLORENE DOPA-15BHF, FLORENE DOPA-33 and FLORENE DOPA-44, and so on. The other resin type pigment dispersant other than the acrylic dispersant may be used singly or in combination of two or more types, or may be used together with the acrylic dispersant.

相對於所使用的100重量份所述顏料(a2)固體，分散劑(a3)的使用量是5重量份至60重量份並更優選15重量份至50重量份。當基於上述標準，分散劑(a3)的含量大於60重量份時，黏度可增加，而當小於5重量份時，顏料霧化可能是困難的或者可以出現在分散後膠凝等的問題。 The dispersant (a3) is used in an amount of 5 parts by weight to 60 parts by weight and more preferably 15 parts by weight to 50 parts by weight relative to 100 parts by weight of the pigment (a2) solid used. When the content of the dispersing agent (a3) is more than 60 parts by weight based on the above criteria, the viscosity may be increased, and when it is less than 5 parts by weight, the atomization of the pigment may be difficult or a problem such as gelation after dispersion may occur.

相對於著色劑(A)中的固體以重量分數計，著色劑(A)中染料的含量優選是0.5重量%至80重量%，更優選0.5重量%至60重量%，特別優選1重量%至50重量%。當基於上述標準，著色劑(A)中的染料含量處於上述範圍內時，它是優選的，因為可以防止圖案形成後由有機溶劑引起的染料洗脫的可靠性下降問題，而且敏感度優異。 The content of the dye in the colorant (A) is preferably from 0.5% by weight to 80% by weight, more preferably from 0.5% by weight to 60% by weight, particularly preferably from 1% by weight to the solids in the coloring agent (A). 50% by weight. When the content of the dye in the colorant (A) is in the above range based on the above criteria, it is preferable because the problem of the reliability of dye elution caused by the organic solvent after pattern formation can be prevented from being lowered, and the sensitivity is excellent.

相對於本發明著色感光樹脂組合物中的總固體，所述著色劑可以占5重量%至60重量%並優選10重量%至50重量%。當著色劑包含在上述範圍內時，即使在形成薄膜時，像素的色濃度仍然充分，並且不減少顯影期間非像素單元的脫失，這是優選的，因為難以出現殘留物。 The colorant may be from 5% by weight to 60% by weight and preferably from 10% by weight to 50% by weight based on the total solids in the colored photosensitive resin composition of the present invention. When the colorant is included in the above range, the color density of the pixel is sufficient even when the film is formed, and the loss of the non-pixel unit during development is not reduced, which is preferable because residue is hard to occur.

本發明的著色感光樹脂組合物中的總固體含量是指在所述著色感光樹脂組合物中，除溶劑以外的組分的總含量。 The total solid content in the colored photosensitive resin composition of the present invention means the total content of components other than the solvent in the colored photosensitive resin composition.

鹼溶性樹脂(B)Alkali soluble resin (B)

本發明的鹼溶性樹脂具有低於0℃的玻璃化轉變溫度，並且特別地，可以包含下面化學式1和化學式2的化合物。通過使用玻璃化轉變溫度低於0℃的鹼溶性樹脂，本發明顯著提高了所述組合物的顯影速率並同樣提高了黏合性，這允許抑制顯影速率增加引起的圖案的短路問題。 The alkali-soluble resin of the present invention has a glass transition temperature of less than 0 ° C, and in particular, may include a compound of the following Chemical Formula 1 and Chemical Formula 2. By using an alkali-soluble resin having a glass transition temperature of less than 0 ° C, the present invention remarkably improves the development rate of the composition and also improves the adhesion, which allows to suppress the short-circuit problem of the pattern caused by an increase in the development rate.

(在化學式1中，n是0或1；R1和R2各自獨立地是氫、或者包含或不包含C1至C12雜原子的脂族或芳族烴；和R3至R6各自獨立地是氫、或者包含或不包含C1至C30雜原子的脂族或芳族烴，並且R3至R6中的兩個可以聯接形成環。) (In Chemical Formula 1, n is 0 or 1; R 1 and R 2 are each independently hydrogen or an aliphatic or aromatic hydrocarbon containing or not containing a C 1 to C 12 hetero atom; and R 3 to R 6 are each Independently hydrogen, or an aliphatic or aromatic hydrocarbon with or without a C 1 to C 30 heteroatom, and two of R 3 to R 6 may be joined to form a ring.)

[化學式2] [Chemical Formula 2]

(在化學式2中，R7獨立地是氫、或者包含或不包含C1至C12雜原子的脂族或芳族烴；和R8是取代或未取代的直鏈或支鏈C2至C30烷基。) (In Chemical Formula 2, R 7 is independently hydrogen or an aliphatic or aromatic hydrocarbon containing or not containing a C 1 to C 12 hetero atom; and R 8 is a substituted or unsubstituted linear or branched C 2 to C 30 alkyl.)

化學式1表示的化合物可以是下列化合物的任何一種。 The compound represented by Chemical Formula 1 may be any one of the following compounds.

包含化學式1或2表示的重複單元的丙烯酸類共聚物在形式上不受限制，亦即，可以具有其中所述重複單元規則重複的嵌段共聚物形式，或具有其中所述重複單元隨機重複的無規共聚物形式。 The acrylic copolymer containing the repeating unit represented by Chemical Formula 1 or 2 is not limited in form, that is, may have a form of a block copolymer in which the repeating unit is regularly repeated, or has a random repeat in which the repeating unit is randomly repeated. Random copolymer form.

另外，化學式2表示的化合物可以包括不飽和羧酸酯例如丙烯酸乙酯、甲基丙烯酸乙酯、丙烯酸正丙酯、 甲基丙烯酸正丙酯、丙烯酸異丙酯、甲基丙烯酸異丙酯、丙烯酸正丁酯、甲基丙烯酸正丁酯、丙烯酸異丁酯、甲基丙烯酸異丁酯、丙烯酸仲丁酯、甲基丙烯酸仲丁酯、丙烯酸叔丁酯、甲基丙烯酸叔丁酯、丙烯酸正戊酯、甲基丙烯酸正戊酯、丙烯酸2-甲基丁酯、甲基丙烯酸2-甲基丁酯、丙烯酸2-乙基丙酯、甲基丙烯酸2-甲基丁酯、丙烯酸正己酯、丙烯酸2-乙基丁酯、丙烯酸2-乙基己酯、甲基丙烯酸2-乙基己酯、丙烯酸正庚酯、丙烯酸正癸酯、丙烯酸正十二烷酯、丙烯酸正十三烷酯、丙烯酸正十六烷酯、丙烯酸正十七烷酯、丙烯酸硬脂醯酯、甲基丙烯酸硬脂醯酯、丙烯酸2,2,3,3-四氟丙酯、丙烯酸3-三甲氧基甲矽烷基丙酯、丙烯酸2-羥乙酯、甲基丙烯酸2-羥乙酯、丙烯酸2-羥丙酯、甲基丙烯酸2-羥丙酯、丙烯酸3-羥丙基酯、甲基丙烯酸3-羥丙酯、丙烯酸2-羥丁酯、甲基丙烯酸2-羥丁酯、丙烯酸3-羥丁酯、甲基丙烯酸3-羥丁酯、丙烯酸4-羥丁酯、甲基丙烯酸4-羥丁酯、丙烯酸烯丙酯、甲基丙烯酸烯丙酯、甲基丙烯酸2-甲氧基乙酯、丙烯酸2-苯氧基乙酯、甲基丙烯酸2-苯氧基乙酯、甲氧基二乙二醇丙烯酸酯、甲氧基二乙二醇甲基丙烯酸酯、甲氧基三乙二醇丙烯酸酯、甲氧基三乙二醇甲基丙烯酸酯、甲氧基丙二醇丙烯酸酯、甲氧基丙二醇甲基丙烯酸酯、甲氧基二丙二醇丙烯酸酯、甲氧基二丙二醇甲基丙烯酸酯、丙烯酸2-羥基-3-苯氧基丙酯、甲基丙烯酸2-羥基-3-苯氧基丙酯、單丙烯酸甘油酯和單甲基丙烯酸甘油酯；不飽和羧酸氨基烷基酯例如丙烯酸2-氨基乙酯、甲基丙烯酸2-氨基乙 酯、丙烯酸2-二甲基氨基乙酯、甲基丙烯酸2-二甲基氨基乙酯、丙烯酸2-氨基丙酯、甲基丙烯酸2-氨基丙酯、丙烯酸2-二甲基氨基丙酯、甲基丙烯酸2-二甲基氨基丙酯、丙烯酸3-氨基丙酯、甲基丙烯酸3-氨基丙酯、丙烯酸3-二甲基氨基丙酯和甲基丙烯酸3-二甲基氨基丙酯；不飽和羧酸縮水甘油酯例如丙烯酸縮水甘油酯和甲基丙烯酸縮水甘油酯；在聚丙烯酸甲酯、聚甲基丙烯酸甲酯、聚丙烯酸正丁酯、聚甲基丙烯酸正丁酯和聚矽氧烷的聚合物分子鏈末端具有單丙烯醯基或單甲基丙烯醯基的大分子單體。 Further, the compound represented by Chemical Formula 2 may include an unsaturated carboxylic acid ester such as ethyl acrylate, ethyl methacrylate, n-propyl acrylate, N-propyl methacrylate, isopropyl acrylate, isopropyl methacrylate, n-butyl acrylate, n-butyl methacrylate, isobutyl acrylate, isobutyl methacrylate, sec-butyl acrylate, methyl Sec-butyl acrylate, tert-butyl acrylate, tert-butyl methacrylate, n-amyl acrylate, n-amyl methacrylate, 2-methylbutyl acrylate, 2-methylbutyl methacrylate, acrylic acid 2- Ethyl propyl ester, 2-methylbutyl methacrylate, n-hexyl acrylate, 2-ethyl butyl acrylate, 2-ethylhexyl acrylate, 2-ethylhexyl methacrylate, n-heptyl acrylate, N-decyl acrylate, n-dodecyl acrylate, n-tridecyl acrylate, n-hexadecane acrylate, n-heptadecanoyl acrylate, stearyl acrylate, stearyl methacrylate, acrylic acid 2, 2,3,3-tetrafluoropropyl ester, 3-trimethoxymethyl propyl propyl acrylate, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl acrylate, methacrylic acid 2 -Hydroxypropyl ester, 3-hydroxypropyl acrylate, 3-hydroxypropyl methacrylate, 2-hydroxybutyl acrylate, 2-hydroxybutyl acrylate, 3-hydroxybutyl acrylate, 3-hydroxybutyl methacrylate, 4-hydroxybutyl acrylate, 4-hydroxybutyl methacrylate, allyl acrylate, methacrylate Ester, 2-methoxyethyl methacrylate, 2-phenoxyethyl acrylate, 2-phenoxyethyl methacrylate, methoxy diethylene glycol acrylate, methoxy diethylene glycol Methacrylate, methoxytriethylene glycol acrylate, methoxytriethylene glycol methacrylate, methoxypropylene glycol acrylate, methoxypropylene glycol methacrylate, methoxydipropylene glycol acrylate , methoxydipropylene glycol methacrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-hydroxy-3-phenoxypropyl methacrylate, glyceryl monoacrylate and glyceryl monomethacrylate An aminoalkyl ester of an unsaturated carboxylic acid such as 2-aminoethyl acrylate or 2-aminoethyl methacrylate Ester, 2-dimethylaminoethyl acrylate, 2-dimethylaminoethyl methacrylate, 2-aminopropyl acrylate, 2-aminopropyl methacrylate, 2-dimethylaminopropyl acrylate, 2-dimethylaminopropyl methacrylate, 3-aminopropyl acrylate, 3-aminopropyl methacrylate, 3-dimethylaminopropyl acrylate and 3-dimethylaminopropyl methacrylate; Unsaturated carboxylic acid glycidyl esters such as glycidyl acrylate and glycidyl methacrylate; in polymethyl acrylate, polymethyl methacrylate, polybutyl acrylate, polybutyl methacrylate and polyoxymethylene The macromolecular monomer having a monopropylene fluorenyl group or a monomethacryl fluorenyl group at the end of the polymer molecular chain of the alkane.

所述鹼溶性樹脂(B)還可以包含下面化學式3表示的化合物。 The alkali-soluble resin (B) may further contain a compound represented by the following Chemical Formula 3.

(在化學式3中，p是1至100的整數；R9是包含由酸酐衍生的羧酸的殘基；和R10和R11各自獨立地是氫或甲基。) (In Chemical Formula 3, p is an integer of 1 to 100; R 9 is a residue containing a carboxylic acid derived from an acid anhydride; and R 10 and R 11 are each independently hydrogen or methyl.)

所述酸酐可以是選自由鄰苯二甲酸酐、(2-十二烯-1-基)琥珀酸酐、馬來酸酐、琥珀酸酐、檸康酸酐、戊二酸酐、甲基琥珀酸酐、3,3-二甲基戊二酸酐、苯基琥珀酸酐、衣康酸酐、3,4,5,6-四氫鄰苯二甲酸酐、偏苯三酸酐、六氫 鄰苯二甲酸酐和降冰片烯二酸酐組成的組中的一種或多種。 The acid anhydride may be selected from the group consisting of phthalic anhydride, (2-dodecen-1-yl) succinic anhydride, maleic anhydride, succinic anhydride, citraconic anhydride, glutaric anhydride, methyl succinic anhydride, 3, 3 - dimethyl glutaric anhydride, phenyl succinic anhydride, itaconic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, trimellitic anhydride, hexahydrogen One or more of the group consisting of phthalic anhydride and norbornene dianhydride.

所述鹼溶性樹脂(B)通過除了化學式1和2表示的重複單元之外還包含化學式3的重複單元而具有低於0℃的玻璃化轉變溫度，因此，顯著提高了組合物的顯影速率並同樣提高了黏合性，這使得抑制了由顯影速率增加引起的圖案短路問題。 The alkali-soluble resin (B) has a glass transition temperature of less than 0 ° C by repeating units of Chemical Formula 3 in addition to the repeating units represented by Chemical Formulas 1 and 2, thereby significantly increasing the developing rate of the composition and The adhesion is also improved, which makes it possible to suppress the pattern short circuit problem caused by an increase in the development rate.

另外，當使用包含所述鹼溶性樹脂(B)的組合物形成圖案時，通過最小化圖案水平的差異可以顯著提高平整度，所述差異可以由於所述組合物中的著色劑而增加，並且通過同樣提高透射率，能夠製造具有優異品質的彩色濾光片。 In addition, when a pattern is formed using the composition containing the alkali-soluble resin (B), the flatness can be remarkably improved by minimizing the difference in pattern level, which may be increased due to the coloring agent in the composition, and By also increasing the transmittance, it is possible to manufacture a color filter having excellent quality.

相對於100mol%的鹼溶性樹脂(B)，包含(A1)來源於化學式1的單元：2mol%至20mol%，(A2)來源於化學式2的構成單元：2mol%至70mol%，和*144來源於化學式3的構成單元(A3)：優選10mol%至90mol%，並且當所述形成比在上述範圍內時，因為顯影性、溶解性和染料之間的平衡良好，可以得到優選的共聚物。 Containing (A1) a unit derived from Chemical Formula 1: 2 mol% to 20 mol%, and (A2) a constituent unit derived from Chemical Formula 2: 2 mol% to 70 mol%, and *144 source, relative to 100 mol% of the alkali-soluble resin (B) The constituent unit (A3) of Chemical Formula 3: preferably 10 mol% to 90 mol%, and when the formation ratio is within the above range, a preferable copolymer can be obtained because the balance between developability, solubility, and dye is good.

所述鹼溶性樹脂(B)可以通過在(A1)至(A3)之外還包括具有不飽和雙鍵的單體(A4)進行共聚而製備。 The alkali-soluble resin (B) can be produced by copolymerization of a monomer (A4) having an unsaturated double bond in addition to (A1) to (A3).

所述具有不飽和雙鍵的可共聚單體的類型沒有特別的限制，其具體例子可以包括芳族乙烯基化合物例如苯乙烯、乙烯基甲苯、α-甲基苯乙烯、對氯苯乙烯、鄰甲 氧基苯乙烯、間甲氧基苯乙烯、對甲氧基苯乙烯、鄰乙烯基苄基甲醚、間乙烯基苄基甲醚、對乙烯基苄基甲醚、鄰乙烯基苄基縮水甘油醚、間乙烯基苄基縮水甘油醚和對乙烯基苄基縮水甘油醚；N-取代的馬來醯亞胺類化合物例如N-環己基馬來醯亞胺、N-苄基馬來醯亞胺、N-苯基馬來醯亞胺、N-鄰羥基苯基馬來醯亞胺、N-間羥基苯基馬來醯亞胺、N-對羥基苯基馬來醯亞胺、N-鄰甲基苯基馬來醯亞胺、N-間甲基苯基馬來醯亞胺、N-對甲基苯基馬來醯亞胺、N-鄰甲氧基苯基馬來醯亞胺、N-間甲氧基苯基馬來醯亞胺和N-對甲氧基苯基馬來醯亞胺；脂環族(甲基)丙烯酸酯例如(甲基)丙烯酸環戊酯、(甲基)丙烯酸環己酯、三環[5.2.1.02,6〕癸-8-基(甲基)丙烯酸酯、2-二環戊氧基乙基(甲基)丙烯酸酯和(甲基)丙烯酸異冰片酯；不飽和氧雜環丁烷化合物例如3-(甲基丙烯醯氧基甲基)氧雜環丁烷、3-(甲基丙烯醯氧基甲基)-3-乙基氧雜環丁烷、3-(甲基丙烯醯氧基甲基)-2-三氟甲基氧雜環丁烷、3-(甲基丙烯醯氧基甲基)-2-苯基氧雜環丁烷、2-(甲基丙烯醯氧基甲基)氧雜環丁烷和2-(甲基丙烯醯氧基甲基)-4-三氟甲基氧雜環丁烷。所述單體可以單獨或作為兩種或更多種類型的組合使用。 The type of the copolymerizable monomer having an unsaturated double bond is not particularly limited, and specific examples thereof may include an aromatic vinyl compound such as styrene, vinyl toluene, α-methylstyrene, p-chlorostyrene, ortho A Oxystyrene, m-methoxystyrene, p-methoxystyrene, o-vinylbenzyl methyl ether, m-vinylbenzyl methyl ether, p-vinylbenzyl methyl ether, o-vinylbenzyl glycidol Ether, m-vinylbenzyl glycidyl ether and p-vinylbenzyl glycidyl ether; N-substituted maleimide compounds such as N-cyclohexylmaleimide, N-benzylmalayiya Amine, N-phenylmaleimide, N-o-hydroxyphenylmaleimide, N-m-hydroxyphenylmaleimide, N-p-hydroxyphenylmaleimide, N- O-methylphenylmaleimide, N-m-methylphenylmaleimide, N-p-methylphenylmaleimide, N-o-methoxyphenylmaleimide , N-m-methoxyphenylmaleimide and N-p-methoxyphenylmaleimide; alicyclic (meth) acrylates such as cyclopentyl (meth) acrylate, (A) Cyclohexyl acrylate, tricyclo[5.2.1.02,6]癸-8-yl (meth) acrylate, 2-dicyclopentyloxyethyl (meth) acrylate and (meth) acrylate Borane ester; unsaturated oxetane compound such as 3-(methacryloxymethyl)oxy Heterocyclobutane, 3-(methacryloxymethyl)-3-ethyloxetane, 3-(methacryloxymethyl)-2-trifluoromethyloxane Butane, 3-(methacryloxymethyl)-2-phenyloxetane, 2-(methacryloxymethyl)oxetane and 2-(methacryl)醯oxymethyl)-4-trifluoromethyloxetane. The monomers may be used singly or in combination of two or more types.

所述具有不飽和雙鍵的可共聚化合物的含量沒有特別的限制，例如，相對於100mol%的鹼溶性樹脂(B)，可以是5mol%至50mol%。當滿足上述範圍時，所述樹脂具有低於0℃的玻璃化轉變溫度，並能夠最小化水平差。 The content of the copolymerizable compound having an unsaturated double bond is not particularly limited, and may be, for example, 5 mol% to 50 mol% with respect to 100 mol% of the alkali-soluble resin (B). When the above range is satisfied, the resin has a glass transition temperature lower than 0 ° C and can minimize the level difference.

在本發明的一種實施方式中，所述共聚物可以利用如同下述那樣的方法作為一個例子，通過共聚製備。 In one embodiment of the present invention, the copolymer can be produced by copolymerization using a method as described below as an example.

(S1)步驟：在配備攪拌器、恒溫器、回流冷卻管、滴液套組和氮氣引入管的燒瓶中將(A1)、(A2)和(甲基)丙烯酸縮水甘油酯共聚；(S2)：上述製備的共聚物同具有羧基的烯式(ethylenic)不飽和單體反應；以及(S3)：反應所述共聚物經歷與酸酐的反應。 (S1) step: copolymerizing (A1), (A2) and glycidyl (meth)acrylate in a flask equipped with a stirrer, a thermostat, a reflux cooling tube, a drip set, and a nitrogen introduction tube; (S2) The copolymer prepared above is reacted with an ethylenic unsaturated monomer having a carboxyl group; and (S3): the copolymer is subjected to a reaction with an acid anhydride.

(S2)步驟是向本發明的鹼溶性樹脂(B)提供光固化性質的步驟，而在(S2)步驟中，所述具有羧基的烯式不飽和單體的類型沒有特別的限制，只要它在表現出所述功能的範圍內即可，並且其例子可以包括(甲基)丙烯酸、乙基丙烯酸、丁基丙烯酸等，優選甲基丙烯酸。 The step (S2) is a step of providing a photocurable property to the alkali-soluble resin (B) of the present invention, and in the step (S2), the type of the ethylenically unsaturated monomer having a carboxyl group is not particularly limited as long as it is It suffices that the function is exhibited, and examples thereof may include (meth)acrylic acid, ethacrylic acid, butylacrylic acid, etc., preferably methacrylic acid.

(S3)步驟是向本發明的鹼溶性樹脂(B)提供適當的酸值的步驟，更具體地說，是通過將來源於所述鹼溶性樹脂的縮水甘油基的羥基與酸酐反應在所述鹼溶性樹脂的側鏈上引入羧基的步驟。 The step (S3) is a step of supplying a suitable acid value to the alkali-soluble resin (B) of the present invention, more specifically, by reacting a hydroxyl group derived from a glycidyl group derived from the alkali-soluble resin with an acid anhydride. A step of introducing a carboxyl group to the side chain of the alkali-soluble resin.

(S3)步驟中使用的酸酐的類型沒有特別的限制，只要它在表現出所述功能的範圍內即可，所述酸酐的例子可以包括鄰苯二甲酸酐、(2-十二烯-1-基)琥珀酸酐、馬來酸酐、琥珀酸酐、檸康酸酐、戊二酸酐、甲基琥珀酸酐、3,3-二甲基戊二酸酐、苯基琥珀酸酐、衣康酸酐、3,4,5,6-四氫鄰苯二甲酸酐、偏苯三酸酐、六氫鄰苯二甲酸酐和降冰片烯二酸酐等，並且根據價格和反應的可利用性，優選馬來 酸酐、鄰苯二甲酸酐、偏苯三酸酐、琥珀酸酐、六氫鄰苯二甲酸酐和降冰片烯二酸酐，更優選偏苯三酸酐、琥珀酸酐和六氫鄰苯二甲酸酐。 The type of the acid anhydride used in the step (S3) is not particularly limited as long as it exhibits the range of the function, and examples of the acid anhydride may include phthalic anhydride, (2-dodecene-1) -yl)succinic anhydride, maleic anhydride, succinic anhydride, citraconic anhydride, glutaric anhydride, methyl succinic anhydride, 3,3-dimethylglutaric anhydride, phenylsuccinic anhydride, itaconic anhydride, 3,4, 5,6-tetrahydrophthalic anhydride, trimellitic anhydride, hexahydrophthalic anhydride, norbornene dianhydride, etc., and depending on the price and availability of the reaction, Malay is preferred. The acid anhydride, phthalic anhydride, trimellitic anhydride, succinic anhydride, hexahydrophthalic anhydride, and norbornene dianhydride are more preferably trimellitic anhydride, succinic anhydride, and hexahydrophthalic anhydride.

為了確保與所述組合物中包含的染料的相容性和所述組合物的儲存穩定性，利用上面描述的製備方法製備的根據本發明製備的鹼溶性樹脂(B)的酸值可以是30mgKOH/g至150mgKOH/g。當所述鹼溶性樹脂(B)具有小於30mgKOH/g的酸值時，所述著色感光樹脂組合物可能難以確保足夠的顯影速率，而當超過150mgKOH/g時，因為與基板的黏合性下降，容易發生圖案短路，並且由於與染料相容性的問題，可以發生所述著色感光樹脂組合物中染料沉澱的問題，或者由於所述著色感光樹脂組合物的儲存穩定性降低，可以發生黏度增加的問題。 The acid value of the alkali-soluble resin (B) prepared according to the present invention prepared by the above-described production method may be 30 mgKOH in order to ensure compatibility with the dye contained in the composition and storage stability of the composition. /g to 150 mgKOH/g. When the alkali-soluble resin (B) has an acid value of less than 30 mgKOH/g, the colored photosensitive resin composition may be difficult to ensure a sufficient development rate, and when it exceeds 150 mgKOH/g, since adhesion to a substrate is lowered, Pattern short-circuiting easily occurs, and the problem of dye precipitation in the colored photosensitive resin composition may occur due to problems with compatibility with the dye, or the viscosity may increase due to a decrease in storage stability of the colored photosensitive resin composition. problem.

在本發明的另一種實施方式中，所述鹼溶性樹脂(B)優選具有在3,000至100,000範圍內的聚苯乙烯換算的重均分子量，更優選在5,000至50,000範圍內。當所述黏合劑樹脂(B)的重均分子量在3,000至100,000範圍內時，它是優選的，因為在顯影期間難以發生膜減少並且非像素部分的脫失傾向是有利的。 In another embodiment of the present invention, the alkali-soluble resin (B) preferably has a polystyrene-equivalent weight average molecular weight in the range of 3,000 to 100,000, more preferably in the range of 5,000 to 50,000. When the weight average molecular weight of the binder resin (B) is in the range of 3,000 to 100,000, it is preferable because it is difficult to cause film reduction during development and the tendency to lose the non-pixel portion is advantageous.

所述鹼溶性樹脂(B)的分子量分佈[重均分子量(Mw)/數均分子量(Mn)]優選從1.5至6.0，更優選從1.8至4.0。具有1.5至6.0的分子量分佈[重均分子量(Mw)/數均分子量(Mn)]由於優異的顯影性從而是有利的。 The molecular weight distribution [weight average molecular weight (Mw) / number average molecular weight (Mn)] of the alkali-soluble resin (B) is preferably from 1.5 to 6.0, more preferably from 1.8 to 4.0. The molecular weight distribution [weight average molecular weight (Mw) / number average molecular weight (Mn)] having a thickness of 1.5 to 6.0 is advantageous because of excellent developability.

相對於所述感光樹脂組合物的總固體重量，本發 明的鹼溶性樹脂(B)的含量沒有特別的限制，例如，從5重量%至80重量%並優選從10重量%至70重量%。當滿足上述範圍時，對顯影溶液的溶解性充分並容易形成圖案，並且因為由於防止了曝光單元的像素部分中的膜減少，非像素部分的脫失變得有利，所以更有利於顯影。 The hair relative to the total solid weight of the photosensitive resin composition The content of the alkali-soluble resin (B) is not particularly limited, and is, for example, from 5% by weight to 80% by weight and preferably from 10% by weight to 70% by weight. When the above range is satisfied, the solubility to the developing solution is sufficient and the pattern is easily formed, and since the loss of the non-pixel portion becomes advantageous because the film in the pixel portion of the exposure unit is prevented from being reduced, development is more advantageous.

光可聚合性化合物(C)Photopolymerizable compound (C)

光可聚合性化合物(C)是通過後面光聚合引發劑(D)的作用可聚合的化合物，可以使用單官能單體、雙官能單體或多官能單體，並可以優選使用雙官能或更高的多官能單體。 The photopolymerizable compound (C) is a compound polymerizable by the action of the latter photopolymerization initiator (D), and a monofunctional monomer, a difunctional monomer or a polyfunctional monomer can be used, and difunctional or more preferably High polyfunctional monomer.

所述單官能單體的具體例子包括丙烯酸壬基苯基卡必醇酯、丙烯酸2-羥基-3-苯氧基丙酯、丙烯酸2-乙基己基卡必醇酯、丙烯酸2-羥基乙酯、N-乙烯基吡咯烷酮等等，但不限於此。 Specific examples of the monofunctional monomer include nonylphenyl carbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexyl carbitol acrylate, 2-hydroxyethyl acrylate , N-vinylpyrrolidone, and the like, but is not limited thereto.

所述雙官能單體的具體例子包括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、三乙二醇二(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)丙烯酸酯等等，但不限於此。 Specific examples of the difunctional monomer include 1,6-hexanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, triethyl Glycol di(meth)acrylate, bis(acryloxyethyl)ether of bisphenol A, 3-methylpentanediol di(meth)acrylate, and the like, but is not limited thereto.

所述多官能單體的具體例子包括三羥甲基丙烷三(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)丙烯酸酯等等，但不限於此。 Specific examples of the polyfunctional monomer include trimethylolpropane tri(meth)acrylate, ethoxylated trimethylolpropane tri(meth)acrylate, propoxylated trimethylolpropane III (meth) acrylate, pentaerythritol tri(meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, ethoxylated dipentaerythritol hexa (meth) acrylate, Propoxylated dipentaerythritol hexa(meth) acrylate, dipentaerythritol hexa (meth) acrylate, etc., but is not limited thereto.

相對於所述感光樹脂組合物的總固體重量，所述光可聚合性化合物占1重量%至60重量%並優選5重量%至50重量%。當包含在上述範圍內的所述光可聚合性化合物時，因為像素單元的強度或平整度變得有利，因而是優選的。 The photopolymerizable compound accounts for 1% by weight to 60% by weight and preferably 5% by weight to 50% by weight based on the total solid weight of the photosensitive resin composition. When the photopolymerizable compound is contained in the above range, it is preferable because the strength or flatness of the pixel unit becomes advantageous.

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

光聚合引發劑(D)的類型沒有特別的限制，只要它能夠聚合所述光可聚合性化合物(C)即可。特別是，根據聚合性質、引發效率、吸收波長、可利用性、價格等等，所述光聚合引發劑(D)優選使用選自由苯乙酮類化合物、二苯甲酮類化合物、三嗪類化合物、聯咪唑類化合物、肟化合物和噻噸酮類化合物組成的組中的一種或多種類型化合物。 The type of the photopolymerization initiator (D) is not particularly limited as long as it can polymerize the photopolymerizable compound (C). In particular, the photopolymerization initiator (D) is preferably selected from the group consisting of acetophenones, benzophenones, and triazines, depending on polymerization properties, initiation efficiency, absorption wavelength, availability, price, and the like. One or more types of compounds in the group consisting of a compound, a biimidazole compound, an anthraquinone compound, and a thioxanthone compound.

所述苯乙酮類化合物的具體例子包括二乙氧基苯乙酮、2-羥基-2-甲基-1-苯基丙-1-酮、苄基二甲基縮酮、2-羥基-1-[4-(2-羥基乙氧基)苯基〕-2-甲基丙-1-酮、1-羥基環己基苯酮、2-甲基-1-(4-甲基苯硫基)-2-嗎啉基丙-1-酮、2-苄基-2-二甲基氨基-1-(4-嗎啉基苯基)丁-1-酮、2-羥基-2-甲基-1-[4-(1-甲基乙烯基)苯基〕丙-1-酮、2-(4-甲基苄基)-2-(二甲氨基)-1-(4-嗎啉基苯基)丁-1-酮等等。 Specific examples of the acetophenone compound include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzyldimethylketal, 2-hydroxy- 1-[4-(2-hydroxyethoxy)phenyl]-2-methylpropan-1-one, 1-hydroxycyclohexyl benzophenone, 2-methyl-1-(4-methylphenylthio) -2-morpholinylpropan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinylphenyl)butan-1-one, 2-hydroxy-2-methyl 1-[4-(1-methylvinyl)phenyl]propan-1-one, 2-(4-methylbenzyl)-2-(dimethylamino)-1-(4-morpholinyl) Phenyl) butan-1-one and the like.

所述二苯甲酮類化合物包括二苯甲酮、鄰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 硫、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等。 The benzophenone compound includes benzophenone, methyl ortho-benzoylbenzoate, 4-phenylbenzophenone, 4-benzylidene-4'-methyldiphenyl Sulfur, 3,3',4,4'-tetrakis(tert-butylperoxycarbonyl)benzophenone, 2,4,6-trimethylbenzophenone, and the like.

所述三嗪類化合物的具體例子包括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-(4-二乙氨基-2-甲苯基)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]-1,3,5-三嗪等等。 Specific examples of the triazine compound include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis (three Chloromethyl)-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperidin-1,3,5-three Pyrazine, 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.

所述聯咪唑化合物的具體例子可以包括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-氯代苯基)-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，或在4,4’,5,5’位的苯基被羧基烷氧基取代的咪唑化合物等等。在這些之中，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’-四苯基聯咪唑和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 may include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole; 2,2'-bis (2,3) -dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole; 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra Alkoxyphenyl)biimidazole; 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetrakis(trialkoxyphenyl)biimidazole; 2,2-double (2,6-Dichlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole, or a phenyl group at the 4,4',5,5' position An alkoxy substituted imidazole compound or the like. Among these, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichloro) is preferably used. Phenyl)-4,4',5,5'-tetraphenylbiimidazole and 2,2-bis(2,6-dichlorophenyl)-4,4',5,5'-tetraphenyl- 1,2'-biimidazole.

所述肟化合物的具體例子可以包括鄰乙氧基羰基-α-氧基亞氨基-1-苯基丙-1-酮等等，典型的商品是BASF公司的OXE01、OXE02。 Specific examples of the hydrazine compound may include o-ethoxycarbonyl-α-oxyimino-1-phenylpropan-1-one and the like, and a typical commercial product is OXE01, OXE02 of BASF Corporation.

所述噻噸酮類化合物包括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-丙氧基噻噸酮等等。 The thioxanthone compound includes 2-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, 1-chloro-4-propoxythioxanthone and many more.

另外，為了提高本發明的著色感光樹脂組合物的敏感度，所述光聚合引發劑(D)還可以包含光聚合引發助劑(d2)。通過含有所述光聚合引發助劑(d2)，所述著色感光樹脂組合物具有增加的敏感度並能夠提高生產率。 Further, in order to increase the sensitivity of the coloring photosensitive resin composition of the present invention, the photopolymerization initiator (D) may further contain a photopolymerization initiation aid (d2). By containing the photopolymerization initiating auxiliary (d2), the colored photosensitive resin composition has increased sensitivity and can improve productivity.

作為(d2)，優選使用選自由胺化合物、羧酸化合物和具有硫醇基的有機硫化合物組成的組中的一種或多種類型化合物。 As (d2), one or more types of 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.

作為胺化合物，優選使用芳族胺化合物，特別是可以使用脂族胺化合物例如三乙醇胺、甲基二乙醇胺和三異丙醇胺、4-二甲氨基苯甲酸甲酯、4-二甲氨基苯甲酸乙酯、4-二甲氨基苯甲酸異戊酯、4-二甲氨基苯甲酸2-乙基己酯、苯甲酸2-二甲氨基乙酯、N,N-二甲基對甲苯胺、4,4'-雙(二甲氨基)二苯甲酮(統稱為米氏酮)、4,4'-雙(二乙氨基)二苯甲酮等等。 As the amine compound, an aromatic amine compound is preferably used, and in particular, aliphatic amine compounds such as triethanolamine, methyldiethanolamine and triisopropanolamine, methyl 4-dimethylaminobenzoate, 4-dimethylaminobenzene can be used. Ethyl formate, isoamyl 4-dimethylaminobenzoate, 2-ethylhexyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, N,N-dimethyl-p-toluidine, 4,4'-bis(dimethylamino)benzophenone (collectively referred to as Michler's ketone), 4,4'-bis(diethylamino)benzophenone, and the like.

所述羧酸優選是芳族雜乙酸，其具體例子可以包括苯基硫代乙酸、甲基苯基硫代乙酸、乙基苯基硫代乙酸、甲基乙基苯基硫代乙酸、二甲基苯基硫代乙酸、甲氧基苯基硫代乙酸、二甲氧基苯基硫代乙酸、氯苯基硫代乙酸、二氯苯基硫代乙酸、N-苯基甘氨酸、苯氧基乙酸、萘基硫代乙酸、N-萘基甘氨酸、萘氧基乙酸等等。 The carboxylic acid is preferably an aromatic heteroacetic acid, and specific examples thereof may include phenylthioacetic acid, methylphenylthioacetic acid, ethylphenylthioacetic acid, methylethylphenylthioacetic acid, and dimethyl Phenylthioacetic acid, methoxyphenylthioacetic acid, dimethoxyphenylthioacetic acid, chlorophenylthioacetic acid, dichlorophenylthioacetic acid, N-phenylglycine, phenoxy Acetic acid, naphthylthioacetic acid, N-naphthylglycine, naphthyloxyacetic acid, and the like.

具有巰基的有機硫化合物的具體例子可以包括 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)、四乙二醇雙(3-巰基丙酸酯)等等。 Specific examples of the organic sulfur compound having a mercapto group may include 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 tetrakis(3-mercaptopropane) Acid ester), dipentaerythritol hexa(3-mercaptopropionate), tetraethylene glycol bis(3-mercaptopropionate), and the like.

相對於本發明的著色感光樹脂組合物的總固體重量，所述光聚合引發劑(D)可以占0.1重量%至40重量%並優選1重量%至30重量%。當所述光聚合引發劑(D)處於上述範圍內時，因為所述著色感光樹脂組合物變得高度敏感，縮短了曝光時間，因此，提高了生產率並保持高解析度，因而是優選的。另外，利用上述條件的組合物形成的像素單元的強度和所述像素單元表面的平整度可以變得有利。 The photopolymerization initiator (D) may be from 0.1% by weight to 40% by weight and preferably from 1% by weight to 30% by weight based on the total solid weight of the colored photosensitive resin composition of the present invention. When the photopolymerization initiator (D) is in the above range, since the colored photosensitive resin composition becomes highly sensitive, the exposure time is shortened, and therefore productivity is improved and high resolution is maintained, and thus it is preferable. In addition, the intensity of the pixel unit formed using the composition of the above conditions and the flatness of the surface of the pixel unit may become advantageous.

此外，當還使用光聚合引發助劑(d2)時，相對於本發明的著色感光樹脂組合物的總固體重量，所述光聚合引發助劑(d2)可以占0.1重量%至50重量%並優選1重量%至40重量%。 Further, when the photopolymerization initiation aid (d2) is also used, the photopolymerization initiating auxiliary (d2) may be from 0.1% by weight to 50% by weight based on the total solid weight of the coloring photosensitive resin composition of the present invention. It is preferably from 1% by weight to 40% by weight.

當(d2)的使用量處於0.1重量%至50重量%的上述範圍內時，所述著色感光樹脂組合物的敏感度進一步提高，獲得增強利用所述組合物形成的彩色濾光片的生產率的效應。 When the amount of use of (d2) is in the above range of from 0.1% by weight to 50% by weight, the sensitivity of the colored photosensitive resin composition is further improved, and the productivity of enhancing the color filter formed using the composition is obtained. effect.

溶劑(E)Solvent (E)

溶劑(E)可以使用在著色感光樹脂組合物中普遍使用的溶劑，沒有限制，只要它有效溶解所述著色感光樹脂組合物中包含的其他組分即可，並且特別是，優選醚、 芳烴、酮、醇、酯、醯胺等等。 The solvent (E) may be a solvent which is generally used in the coloring photosensitive resin composition, and is not limited as long as it is effective for dissolving other components contained in the colored photosensitive resin composition, and particularly, ether, Aromatic hydrocarbons, ketones, alcohols, esters, decylamines, and the like.

溶劑(E)的具體例子可以包括乙二醇單烷醚例如乙二醇單甲醚、乙二醇單乙醚、乙二醇單丙醚和乙二醇單丁醚，二乙二醇二烷基醚例如二乙二醇二甲醚、二乙二醇二乙醚、二乙二醇二丙醚和二乙二醇二丁醚，乙二醇烷基醚乙酸酯例如甲基溶纖劑乙酸酯和乙基溶纖劑乙酸酯，亞烷基二醇烷基醚乙酸酯例如丙二醇單甲醚乙酸酯、丙二醇單乙醚乙酸酯、丙二醇單丙醚乙酸酯、乙酸甲氧基丁酯和乙酸甲氧基戊酯，芳烴例如苯、甲苯、二甲苯和均三甲苯，酮，例如甲乙酮、丙酮、甲基戊基酮、甲基異丁基酮、環己酮，醇，例如乙醇、丙醇、丁醇、己醇、環己醇、乙二醇、甘油和4-羥基-4-甲基-2-戊酮，酯，例如3-乙氧基丙酸乙酯、3-甲氧基丙酸甲酯、環酯例如γ-丁內酯，等等。 Specific examples of the solvent (E) may include ethylene glycol monoalkyl ethers 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 diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether and diethylene glycol dibutyl ether, ethylene glycol alkyl ether acetate such as methyl cellosolve acetic acid Ester and ethyl cellosolve acetate, alkylene glycol alkyl ether acetate such as propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, methoxy acetate Butyl ester and methoxypentyl acetate, aromatic hydrocarbons such as benzene, toluene, xylene and mesitylene, ketones such as methyl ethyl ketone, acetone, methyl amyl ketone, methyl isobutyl ketone, cyclohexanone, alcohol, for example Ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, glycerol and 4-hydroxy-4-methyl-2-pentanone, esters such as ethyl 3-ethoxypropionate, 3- Methyl methoxypropionate, a cyclic ester such as γ-butyrolactone, and the like.

根據塗布性能和乾燥性能，所述溶劑(E)優選是沸點為100℃至200℃的有機溶劑，更優選地，可以使用丙二醇單甲醚乙酸酯、丙二醇單乙醚乙酸酯、環己酮、乳酸乙酯、乳酸丁酯、3-乙氧基丙酸乙酯、3-甲氧基丙酸甲酯等等，並優選與能夠通過抑制染料沉澱而改善儲存穩定性的醇類溶劑例如4-羥基-4-甲基-2-戊酮混合。 The solvent (E) is preferably an organic solvent having a boiling point of from 100 ° C to 200 ° C depending on coating properties and drying properties, and more preferably, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, cyclohexanone may be used. , ethyl lactate, butyl lactate, ethyl 3-ethoxypropionate, methyl 3-methoxypropionate, etc., and preferably with an alcohol solvent capable of improving storage stability by inhibiting dye precipitation, for example 4 -Hydroxy-4-methyl-2-pentanone is mixed.

所述溶劑可以單獨或作為兩種或更多種類型的混合物使用，並且，相對於所述著色感光樹脂組合物的總重量，可以占60重量%至90重量%並優選70重量%至85重量%。當占這樣的含量時，當用塗層設備例如輥塗機、旋塗機、狹縫式旋塗機、狹縫式塗布機(有時稱為模頭塗布機)和噴墨機塗敷時，塗布性能變得有利。 The solvent may be used singly or as a mixture of two or more types, and may be 60% by weight to 90% by weight and preferably 70% by weight to 85% by weight based on the total weight of the colored photosensitive resin composition. %. When such content is used, when coated with a coating apparatus such as a roll coater, a spin coater, a slit coater, a slit coater (sometimes referred to as a die coater), and an ink jet machine The coating properties become advantageous.

*223添加劑(F)*223 Additives (F)

添加劑(F)可以根據需要選擇性添加，其例子可以包括其他聚合物化合物、固化劑、表面活性劑、助黏劑、抗氧化劑、紫外線吸收劑和解聚結劑。 The additive (F) may be optionally added as needed, and examples thereof may include other polymer compounds, curing agents, surfactants, adhesion promoters, antioxidants, ultraviolet absorbers, and deagglomerating agents.

所述其他聚合物化合物的具體例子可以包括固化樹脂例如環氧樹脂和馬來醯亞胺樹脂、和熱塑性樹脂例如聚乙烯醇、聚丙烯酸、聚乙二醇單烷基醚、聚氟代烷基丙烯酸酯、聚酯和聚氨酯。 Specific examples of the other polymer compound may include a cured resin such as an epoxy resin and a maleimide resin, and a thermoplastic resin such as polyvinyl alcohol, polyacrylic acid, polyethylene glycol monoalkyl ether, polyfluoroalkyl group. Acrylates, polyesters and polyurethanes.

所述固化劑用於深度固化和提高機械強度，並且所述固化劑的具體例子可以包括環氧化合物、多官能異氰酸酯化合物、三聚氰胺化合物、氧雜環丁烷化合物等等。 The curing agent is used for deep curing and mechanical strength improvement, and specific examples of the curing agent may include an epoxy compound, a polyfunctional isocyanate compound, a melamine compound, an oxetane compound, and the like.

所述固化劑中的環氧化合物的具體例子可以包括雙酚A類環氧樹脂、氫化雙酚A類環氧樹脂、雙酚F類環氧樹脂、氫化雙酚F類環氧樹脂、酚醛清漆型環氧樹脂、其他芳族類環氧樹脂、脂環族類環氧樹脂、縮水甘油酯類樹脂、縮水甘油胺類樹脂、或這樣的環氧樹脂的溴化衍生物、環氧樹脂以外的脂族、脂環族或芳族環氧化合物及其溴化衍生物、丁二烯(共)聚合物環氧化物、異戊二烯(共)聚合物 環氧化物、(甲基)丙烯酸縮水甘油酯(共)聚合物、異氰脲酸三縮水甘油酯等等。 Specific examples of the epoxy compound in the curing agent may include bisphenol A epoxy resin, hydrogenated bisphenol A epoxy resin, bisphenol F epoxy resin, hydrogenated bisphenol F epoxy resin, novolac Type epoxy resin, other aromatic epoxy resin, alicyclic epoxy resin, glycidyl ester resin, glycidylamine resin, or a brominated derivative of such an epoxy resin, or an epoxy resin Aliphatic, alicyclic or aromatic epoxy compounds and their brominated derivatives, butadiene (co)polymer epoxides, isoprene (co)polymers Epoxide, glycidyl (meth)acrylate (co)polymer, triglycidyl isocyanurate, and the like.

所述固化劑中氧雜環丁烷化合物的具體例子可以包括碳酸酯雙氧雜環丁烷、二甲苯雙氧雜環丁烷、己二酸酯雙氧雜環丁烷、對苯二甲酸酯雙氧雜環丁烷、環己烷二羧酸雙氧雜環丁烷等等。 Specific examples of the oxetane compound in the curing agent may include carbonate dioxetane, xylene dioxetane, adipate dioxetane, terephthalic acid Ester dioxetane, cyclohexane dicarboxylic acid dioxetane, and the like.

所述固化劑可以使用能夠與固化劑一起將所述環氧化合物的環氧基和所述氧雜環丁烷化合物的氧雜環丁烷骨架開環聚合的固化助劑化合物。所述固化助劑化合物的例子包括多價碳酸、多價碳酸酐、產酸劑等等。作為所述多價碳酸酐，可以使用可作為環氧樹脂固化劑商購的化合物。所述環氧樹脂固化劑的具體例子可以包括商品名(Adeka primer EH-700)(Adeka Corporation製造)，商品名(Rikacid HH)(New Japan Chemical Co.,Ltd.製造)，商品名(MH-700)(New Japan Chemical Co.,Ltd.製造)等等。以上舉例說明的固化劑可以單獨或作為兩種或更多種類的混合物使用。 As the curing agent, a curing assistant compound capable of ring-opening polymerization of an epoxy group of the epoxy compound and an oxetane skeleton of the oxetane compound together with a curing agent can be used. Examples of the curing assistant compound include polyvalent carbonic acid, polyvalent carbonic anhydride, an acid generator, and the like. As the polyvalent carbonic anhydride, a compound which is commercially available as an epoxy resin curing agent can be used. Specific examples of the epoxy resin curing agent may include a trade name (Adeka primer EH-700) (manufactured by Adeka Corporation), trade name (Rikacid HH) (manufactured by New Japan Chemical Co., Ltd.), trade name (MH- 700) (manufactured by New Japan Chemical Co., Ltd.) and the like. The curing agents exemplified above may be used singly or as a mixture of two or more kinds.

所述表面活性劑可以用於進一步提高所述著色感光樹脂組合物的成膜性質，並可以優選使用氟類、有機矽類表面活性劑等等。 The surfactant can be used to further improve the film-forming property of the colored photosensitive resin composition, and a fluorine-based, organic anthraquinone-based surfactant or the like can be preferably used.

作為商品，所述有機矽基表面活性劑的例子包括，Dow Corning Toray Silicone Co.,Ltd.製造的DC3PA、DC7PA、SH11PA、SH21PA、SH8400等，和GE Toshiba Silicone Co.,Ltd.製造的TSF-4440、TSF-4300、TSF-4445、TSF-4446、 TSF-4460、TSF-4452等。作為商品，所述氟類表面活性劑的例子包括，DIC Corporation製造的Megafac F-470、F-471、F-475、F-482、F-489等。以上舉例說明的表面活性劑可以單獨或作為兩種或更多種類型的組合使用。 As a commercial product, examples of the organic fluorene-based surfactant include DC3PA, DC7PA, SH11PA, SH21PA, SH8400, and the like manufactured by Dow Corning Toray Silicone Co., Ltd., and TSF- manufactured by GE Toshiba Silicone Co., Ltd. 4440, TSF-4300, TSF-4445, TSF-4446, TSF-4460, TSF-4452, etc. As a commercial product, examples of the fluorine-based surfactant include Megafac F-470, F-471, F-475, F-482, F-489, and the like manufactured by DIC Corporation. The surfactants exemplified above may be used singly or in combination of two or more types.

助黏劑的具體例子可以包括乙烯基三甲氧基矽烷、乙烯基三乙氧基矽烷、乙烯基三(2-甲氧基乙氧基)矽烷、N-(2-氨基乙基)-3-氨基丙基甲基二甲氧基矽烷、N-(2-氨基乙基)-3-氨基丙基三甲氧基矽烷、3-氨基丙基三乙氧基矽烷、3-縮水甘油醚氧丙基三甲氧基矽烷、3-縮水甘油醚氧丙基甲基二甲氧基矽烷、2-(3,4-環氧基環己基)乙基三甲氧基矽烷、3-氯丙基甲基二甲氧基矽烷、3-氯丙基三甲氧基矽烷、3-甲基丙烯醯氧基丙基三甲氧基矽烷、3-巰基丙基三甲氧基矽烷、3-異氰酸酯丙基三甲氧基矽烷、3-異氰酸酯丙基三乙氧基矽烷等等。以上舉例說明的助黏劑可以單獨或作為兩種或更多種類型的組合使用。相對於所述著色感光樹脂組合物的總固體重量，所述助黏劑通常可以占0.01重量%至10重量%並優選0.05重量%至2重量%。 Specific examples of the adhesion promoter may include vinyltrimethoxydecane, vinyltriethoxydecane, vinyltris(2-methoxyethoxy)decane, N-(2-aminoethyl)-3- Aminopropylmethyldimethoxydecane, N-(2-aminoethyl)-3-aminopropyltrimethoxydecane, 3-aminopropyltriethoxydecane, 3-glycidyloxypropyl Trimethoxydecane, 3-glycidyloxypropylmethyldimethoxydecane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxydecane, 3-chloropropylmethyldimethyl Oxydecane, 3-chloropropyltrimethoxydecane, 3-methylpropenyloxypropyltrimethoxydecane, 3-mercaptopropyltrimethoxydecane, 3-isocyanatepropyltrimethoxydecane, 3 - Isocyanate propyl triethoxy decane and the like. The adhesion promoters exemplified above may be used singly or in combination of two or more types. The adhesion promoter may generally be from 0.01% by weight to 10% by weight and preferably from 0.05% by weight to 2% by weight, based on the total solid weight of the colored photosensitive resin composition.

所述抗氧化劑的具體例子可以包括2,2'-硫代雙(4-甲基-6-叔丁基苯酚)、2,6-二叔丁基-4-甲基苯酚等等。 Specific examples of the antioxidant may include 2,2'-thiobis(4-methyl-6-tert-butylphenol), 2,6-di-tert-butyl-4-methylphenol, and the like.

紫外線吸收劑的具體例子可以包括2-(3-叔丁基-2-羥基-5-甲苯基)-5-氯苯并三唑、烷氧基二苯甲酮等等。 Specific examples of the ultraviolet absorber may include 2-(3-tert-butyl-2-hydroxy-5-tolyl)-5-chlorobenzotriazole, alkoxybenzophenone and the like.

所述解聚結劑的具體例子可以包括聚丙烯酸鈉等等。 Specific examples of the deagglomerating agent may include sodium polyacrylate and the like.

本發明的著色感光樹脂組合物的製備方法的例 子描述如下。 An example of a method for preparing the colored photosensitive resin composition of the present invention The sub-described is as follows.

首先，將著色劑(A)中的顏料(a2)與溶劑(E)混合並利用珠磨機等分散，直到所述顏料的平均粒徑變成大約0.2μm或更小。在此，根據需要，顏料分散劑(a3)、一部分或全部的所述鹼溶性樹脂(B)或染料(a1)可以與溶劑(E)混合，並溶解或分散。 First, the pigment (a2) in the colorant (A) is mixed with the solvent (E) and dispersed by a bead mill or the like until the average particle diameter of the pigment becomes about 0.2 μm or less. Here, the pigment dispersant (a3), a part or all of the alkali-soluble resin (B) or the dye (a1) may be mixed with the solvent (E) and dissolved or dispersed, as needed.

向所述混合的分散液進一步添加染料(a1)、剩餘的鹼溶性樹脂(B)、光可聚合性化合物(C)、光聚合引發劑(D)、根據需要的添加劑(F)，以及溶劑(E)，使得具有特定的濃度，並可以製備本發明的著色感光樹脂組合物。 Further, a dye (a1), a remaining alkali-soluble resin (B), a photopolymerizable compound (C), a photopolymerization initiator (D), an optional additive (F), and a solvent are added to the mixed dispersion. (E) is made to have a specific concentration, and the colored photosensitive resin composition of the present invention can be prepared.

本發明包括利用所述著色感光樹脂組合物製造的彩色濾光片，和包含所述彩色濾光片的液晶顯示裝置。本發明的彩色濾光片和液晶顯示裝置可以利用已知的方法製造。 The present invention includes a color filter manufactured using the colored photosensitive resin composition, and a liquid crystal display device including the color filter. The color filter and liquid crystal display device of the present invention can be produced by a known method.

在下文中，將基於實施例更詳細地描述本發明，然而，在下面公開的本發明的實施方式只是說明，並且本發明的範圍不限於這些實施方式。本發明的範圍在申請專利範圍中表達，此外，包含與所述申請專利範圍的記錄等效的含義和範圍內的全部修改。另外，在實施例和比較例中表示含量的“%”和“份”是基於重量，除非另有具體說明。 Hereinafter, the present invention will be described in more detail based on the examples, however, the embodiments of the invention disclosed below are merely illustrative, and the scope of the invention is not limited to the embodiments. The scope of the present invention is expressed by the scope of the claims, and all modifications within the meaning and range equivalent to the records of the claims are included. In addition, "%" and "part" indicating the content in the examples and comparative examples are based on weight unless otherwise specifically stated.

製備例：顏料分散組合物的製備Preparation Example: Preparation of Pigment Dispersion Composition

<顏料分散組合物M1> <Pigment Dispersion Composition M1>

將作為顏料的12.0重量份C.I.顏料紅177、作為顏 料分散劑的4.0重量份DISPERBYK-2001(BYK Chemie製造)、1.2重量份酸性紅52、以及作為溶劑的44重量份丙二醇甲醚乙酸酯和20重量份4-羥基-4-甲基-2-戊酮利用珠磨機混合/分散12小時，製備顏料分散液M1。 12.0 parts by weight of C.I. Pigment Red 177 as a pigment, as a pigment 4.0 parts by weight of DISPERBYK-2001 (manufactured by BYK Chemie), 1.2 parts by weight of acid red 52, and 44 parts by weight of propylene glycol methyl ether acetate and 20 parts by weight of 4-hydroxy-4-methyl-2 as a solvent. The pentanone was mixed/dispersed by a bead mill for 12 hours to prepare a pigment dispersion M1.

<顏料分散組合物M2> <Pigment Dispersion Composition M2>

將作為顏料的13.2重量份C.I.顏料紅177、作為顏料分散劑的4.0重量份DISPERBYK-2001(BYK Chemie製造)、作為溶劑的44重量份丙二醇甲醚乙酸酯和20重量份4-羥基-4-甲基-2-戊酮利用珠磨機混合/分散12小時，製備顏料分散液M2。 13.2 parts by weight of CI Pigment Red 177 as a pigment, 4.0 parts by weight of DISPERBYK-2001 (manufactured by BYK Chemie) as a pigment dispersant, 44 parts by weight of propylene glycol methyl ether acetate as a solvent, and 20 parts by weight of 4-hydroxy-4 -Methyl-2-pentanone was mixed/dispersed by a bead mill for 12 hours to prepare a pigment dispersion M2.

合成例：鹼溶性樹脂的合成Synthesis example: Synthesis of alkali-soluble resin

<合成例1> <Synthesis Example 1>

利用2-降冰片烯和丙烯酸2-乙基己酯作為本申請的化學式1化合物和化學式2化合物，如下合成鹼溶性樹脂。 Using 2-norbornene and 2-ethylhexyl acrylate as the compound of Chemical Formula 1 and the compound of Chemical Formula 2 of the present application, an alkali-soluble resin is synthesized as follows.

向配備攪拌器、恒溫器、回流冷卻管、滴液套組和氮氣引入管的燒瓶添加90g的丙二醇單甲醚乙酸酯和90g的丙二醇單甲醚，並在燒瓶中的氣體從空氣轉換為氮氣後，向其引入8.2g的偶氮雙異丁腈、4.7g的2-降冰片烯、55.2g的丙烯酸2-乙基己酯、5.9g的4-甲基苯乙烯、85.2g的甲基丙烯酸縮水甘油酯和6.0g的正十二硫醇。之後，在攪拌生成物的同時將所述反應溶液的溫度升高到80℃，並將所述生成物反應8小時。 To a flask equipped with a stirrer, a thermostat, a reflux cooling tube, a drip set, and a nitrogen introduction tube, 90 g of propylene glycol monomethyl ether acetate and 90 g of propylene glycol monomethyl ether were added, and the gas in the flask was converted from air to After nitrogen, 8.2 g of azobisisobutyronitrile, 4.7 g of 2-norbornene, 55.2 g of 2-ethylhexyl acrylate, 5.9 g of 4-methylstyrene, and 85.2 g of A were introduced. Glycidyl acrylate and 6.0 g of n-dodecyl mercaptan. Thereafter, the temperature of the reaction solution was raised to 80 ° C while stirring the product, and the resultant was reacted for 8 hours.

所述反應溶液的溫度降至室溫，並在所述燒瓶中 的氣體從氮氣轉換到空氣後，0.2g的三乙胺、0.1g的4-甲氧基苯酚和43.2g的丙烯酸與136g的丙二醇單甲醚乙酸酯一起從滴液套組滴入2小時，並將生成物在100℃下反應6小時。之後，所述反應溶液的溫度降至室溫，向其引入6.0g琥珀酸酐，並將生成物在80℃下攪拌6小時。 The temperature of the reaction solution was lowered to room temperature and in the flask After the gas was switched from nitrogen to air, 0.2 g of triethylamine, 0.1 g of 4-methoxyphenol and 43.2 g of acrylic acid were added dropwise from the drip set for 2 hours together with 136 g of propylene glycol monomethyl ether acetate. The product was reacted at 100 ° C for 6 hours. Thereafter, the temperature of the reaction solution was lowered to room temperature, 6.0 g of succinic anhydride was introduced thereto, and the resultant was stirred at 80 ° C for 6 hours.

如上合成的鹼溶性樹脂的固體酸值為35.8mg KOH/g，並且用GPC測量的重均分子量Mw為大約7350。 The alkali-soluble resin synthesized as above had a solid acid value of 35.8 mg KOH/g, and the weight average molecular weight Mw measured by GPC was about 7,350.

利用差示掃描量熱術測量玻璃化轉變溫度的結果是-18℃。 The result of measuring the glass transition temperature by differential scanning calorimetry was -18 °C.

<合成例2> <Synthesis Example 2>

利用2-降冰片烯和丙烯酸2-乙基己酯作為本申請的化學式1化合物和化學式2化合物，如下合成鹼溶性樹脂。 Using 2-norbornene and 2-ethylhexyl acrylate as the compound of Chemical Formula 1 and the compound of Chemical Formula 2 of the present application, an alkali-soluble resin is synthesized as follows.

向配備攪拌器、恒溫器、回流冷卻管、滴液套組和氮氣引入管的燒瓶添加90g的丙二醇單甲醚乙酸酯和90g的丙二醇單甲醚，並在燒瓶中的氣體從空氣轉換為氮氣後，向其引入8.2g的偶氮雙異丁腈、4.7g的2-降冰片烯、55.2g的丙烯酸2-乙基己酯、5.9g的4-甲基苯乙烯、85.2g的甲基丙烯酸縮水甘油酯和6.0g的正十二硫醇。之後，在攪拌生成物的同時將所述反應溶液的溫度升高到80℃，並將所述生成物反應4小時。 To a flask equipped with a stirrer, a thermostat, a reflux cooling tube, a drip set, and a nitrogen introduction tube, 90 g of propylene glycol monomethyl ether acetate and 90 g of propylene glycol monomethyl ether were added, and the gas in the flask was converted from air to After nitrogen, 8.2 g of azobisisobutyronitrile, 4.7 g of 2-norbornene, 55.2 g of 2-ethylhexyl acrylate, 5.9 g of 4-methylstyrene, and 85.2 g of A were introduced. Glycidyl acrylate and 6.0 g of n-dodecyl mercaptan. Thereafter, the temperature of the reaction solution was raised to 80 ° C while stirring the product, and the resultant was reacted for 4 hours.

所述反應溶液的溫度降至室溫，並在所述燒瓶中的氣體從氮氣轉換到空氣後，0.2g的三乙胺、0.1g的4-甲氧基苯酚和43.2g的丙烯酸與136g的丙二醇單甲醚乙酸酯一 起從滴液套組滴入2小時，並將生成物在100℃下反應6小時。之後，所述反應溶液的溫度降至室溫，向其引入12.5g琥珀酸酐，並將生成物在80℃下攪拌6小時。 The temperature of the reaction solution was lowered to room temperature, and after the gas in the flask was switched from nitrogen to air, 0.2 g of triethylamine, 0.1 g of 4-methoxyphenol, and 43.2 g of acrylic acid and 136 g of Propylene glycol monomethyl ether acetate The mixture was dropped from the drip set for 2 hours, and the resultant was reacted at 100 ° C for 6 hours. Thereafter, the temperature of the reaction solution was lowered to room temperature, 12.5 g of succinic anhydride was introduced thereto, and the resultant was stirred at 80 ° C for 6 hours.

如上合成的鹼溶性樹脂的固體酸值為69.6mg KOH/g，並且用GPC測量的重均分子量Mw為大約6370。 The alkali-soluble resin synthesized as above had a solid acid value of 69.6 mg KOH/g, and the weight average molecular weight Mw measured by GPC was about 6,370.

利用差示掃描量熱術測量玻璃化轉變溫度的結果是-25.3℃。 The result of measuring the glass transition temperature by differential scanning calorimetry was -25.3 °C.

<合成例3> <Synthesis Example 3>

利用2-降冰片烯和丙烯酸正丁酯作為本申請的化學式1化合物和化學式2化合物，如下合成鹼溶性樹脂。 Using 2-norbornene and n-butyl acrylate as the compound of Chemical Formula 1 and the compound of Chemical Formula 2 of the present application, an alkali-soluble resin is synthesized as follows.

向配備攪拌器、恒溫器、回流冷卻管、滴液套組和氮氣引入管的燒瓶添加90g的丙二醇單甲醚乙酸酯和90g的丙二醇單甲醚，並在燒瓶中的氣體從空氣轉換為氮氣後，向其引入8.2g的偶氮雙異丁腈、4.7g的2-降冰片烯、38.4g的丙烯酸正丁酯、5.9g的4-甲基苯乙烯、85.2g的甲基丙烯酸縮水甘油酯和6.0g的正十二硫醇。之後，在攪拌生成物的同時將所述反應溶液的溫度升高到80℃，並將所述生成物反應4小時。 To a flask equipped with a stirrer, a thermostat, a reflux cooling tube, a drip set, and a nitrogen introduction tube, 90 g of propylene glycol monomethyl ether acetate and 90 g of propylene glycol monomethyl ether were added, and the gas in the flask was converted from air to After nitrogen, 8.2 g of azobisisobutyronitrile, 4.7 g of 2-norbornene, 38.4 g of n-butyl acrylate, 5.9 g of 4-methylstyrene, and 85.2 g of methacrylic acid were introduced. Glyceride and 6.0 g of n-dodecyl mercaptan. Thereafter, the temperature of the reaction solution was raised to 80 ° C while stirring the product, and the resultant was reacted for 4 hours.

*281所述反應溶液的溫度降至室溫，並在所述燒瓶中的氣體從氮氣轉換到空氣後，0.2g的三乙胺、0.1g的4-甲氧基苯酚和43.2g的丙烯酸與136g的丙二醇單甲醚乙酸酯一起從滴液套組滴入2小時，並將生成物在100℃下反應6小時。之後，所述反應溶液的溫度降至室溫，向其引入6.0g琥珀酸酐，並將生成物在80℃下攪拌6小時。 *281 The temperature of the reaction solution was lowered to room temperature, and after the gas in the flask was switched from nitrogen to air, 0.2 g of triethylamine, 0.1 g of 4-methoxyphenol and 43.2 g of acrylic acid were used. 136 g of propylene glycol monomethyl ether acetate was dropped together from the drip set for 2 hours, and the resultant was reacted at 100 ° C for 6 hours. Thereafter, the temperature of the reaction solution was lowered to room temperature, 6.0 g of succinic anhydride was introduced thereto, and the resultant was stirred at 80 ° C for 6 hours.

如上合成的鹼溶性樹脂的固體酸值為37.2mg KOH/g，並且用GPC測量的重均分子量Mw為大約5870。 The alkali-soluble resin synthesized as above had a solid acid value of 37.2 mg KOH/g, and the weight average molecular weight Mw measured by GPC was about 5,870.

利用差示掃描量熱術測量玻璃化轉變溫度的結果是-8.3℃。 The result of measuring the glass transition temperature by differential scanning calorimetry was -8.3 °C.

<合成例4> <Synthesis Example 4>

利用2-降冰片烯和丙烯酸正十六烷基酯作為本申請的化學式1化合物和化學式2化合物，如下合成鹼溶性樹脂。 Using 2-norbornene and n-hexadecyl acrylate as the compound of Chemical Formula 1 and the compound of Chemical Formula 2 of the present application, an alkali-soluble resin is synthesized as follows.

向配備攪拌器、恒溫器、回流冷卻管、滴液套組和氮氣引入管的燒瓶添加90g的丙二醇單甲醚乙酸酯和90g的丙二醇單甲醚，並在燒瓶中的氣體從空氣轉換為氮氣後，向其引入8.2g的偶氮雙異丁腈、4.7g的2-降冰片烯、88.8g的丙烯酸正十六烷基酯、5.9g的4-甲基苯乙烯、85.2g的甲基丙烯酸縮水甘油酯和6.0g的正十二硫醇。之後，在攪拌生成物的同時將所述反應溶液的溫度升高到80℃，並將所述生成物反應4小時。 To a flask equipped with a stirrer, a thermostat, a reflux cooling tube, a drip set, and a nitrogen introduction tube, 90 g of propylene glycol monomethyl ether acetate and 90 g of propylene glycol monomethyl ether were added, and the gas in the flask was converted from air to After nitrogen, 8.2 g of azobisisobutyronitrile, 4.7 g of 2-norbornene, 88.8 g of n-hexadecyl acrylate, 5.9 g of 4-methylstyrene, and 85.2 g of A were introduced. Glycidyl acrylate and 6.0 g of n-dodecyl mercaptan. Thereafter, the temperature of the reaction solution was raised to 80 ° C while stirring the product, and the resultant was reacted for 4 hours.

所述反應溶液的溫度降至室溫，並在所述燒瓶中的氣體從氮氣轉換到空氣後，0.2g的三乙胺、0.1g的4-甲氧基苯酚和43.2g的丙烯酸與136g的丙二醇單甲醚乙酸酯一起從滴液套組滴入2小時，並將生成物在100℃下反應6小時。之後，所述反應溶液的溫度降至室溫，向其引入6.0g琥珀酸酐，並將生成物在80℃下攪拌6小時。 The temperature of the reaction solution was lowered to room temperature, and after the gas in the flask was switched from nitrogen to air, 0.2 g of triethylamine, 0.1 g of 4-methoxyphenol, and 43.2 g of acrylic acid and 136 g of Propylene glycol monomethyl ether acetate was added dropwise from the drip set for 2 hours, and the resultant was reacted at 100 ° C for 6 hours. Thereafter, the temperature of the reaction solution was lowered to room temperature, 6.0 g of succinic anhydride was introduced thereto, and the resultant was stirred at 80 ° C for 6 hours.

如上合成的鹼溶性樹脂的固體酸值為38.0mg KOH/g，並且用GPC測量的重均分子量Mw為大約7530。 The alkali-soluble resin synthesized as above had a solid acid value of 38.0 mg KOH/g, and the weight average molecular weight Mw measured by GPC was about 7530.

利用差示掃描量熱術測量玻璃化轉變溫度的結果是-45.0℃。 The result of measuring the glass transition temperature by differential scanning calorimetry was -45.0 °C.

<合成例5> <Synthesis Example 5>

利用2-降冰片烯和丙烯酸正十六烷基酯作為本申請的化學式1化合物和化學式2化合物，如下合成鹼溶性樹脂。 Using 2-norbornene and n-hexadecyl acrylate as the compound of Chemical Formula 1 and the compound of Chemical Formula 2 of the present application, an alkali-soluble resin is synthesized as follows.

向配備攪拌器、恒溫器、回流冷卻管、滴液套組和氮氣引入管的燒瓶添加90g的丙二醇單甲醚乙酸酯和90g的丙二醇單甲醚，並在燒瓶中的氣體從空氣轉換為氮氣後，向其引入8.2g的偶氮雙異丁腈、9.4g的2-降冰片烯、88.8g的丙烯酸正十六烷基酯、85.2g的甲基丙烯酸縮水甘油酯和6.0g的正十二硫醇。之後，在攪拌生成物的同時將所述反應溶液的溫度升高到80℃，並將所述生成物反應4小時。 To a flask equipped with a stirrer, a thermostat, a reflux cooling tube, a drip set, and a nitrogen introduction tube, 90 g of propylene glycol monomethyl ether acetate and 90 g of propylene glycol monomethyl ether were added, and the gas in the flask was converted from air to After nitrogen, 8.2 g of azobisisobutyronitrile, 9.4 g of 2-norbornene, 88.8 g of n-hexadecyl acrylate, 85.2 g of glycidyl methacrylate and 6.0 g of positive were introduced thereto. Dodecanol. Thereafter, the temperature of the reaction solution was raised to 80 ° C while stirring the product, and the resultant was reacted for 4 hours.

所述反應溶液的溫度降至室溫，並在所述燒瓶中的氣體從氮氣轉換到空氣後，0.2g的三乙胺、0.1g的4-甲氧基苯酚和43.2g的丙烯酸與136g的丙二醇單甲醚乙酸酯一起從滴液套組滴入2小時，並將生成物在100℃下反應6小時。之後，所述反應溶液的溫度降至室溫，向其引入6.0g琥珀酸酐，並將生成物在80℃下攪拌6小時。 The temperature of the reaction solution was lowered to room temperature, and after the gas in the flask was switched from nitrogen to air, 0.2 g of triethylamine, 0.1 g of 4-methoxyphenol, and 43.2 g of acrylic acid and 136 g of Propylene glycol monomethyl ether acetate was added dropwise from the drip set for 2 hours, and the resultant was reacted at 100 ° C for 6 hours. Thereafter, the temperature of the reaction solution was lowered to room temperature, 6.0 g of succinic anhydride was introduced thereto, and the resultant was stirred at 80 ° C for 6 hours.

如上合成的鹼溶性樹脂的固體酸值為36.0mg KOH/g，並且用GPC測量的重均分子量Mw為大約6530。 The alkali-soluble resin synthesized as above had a solid acid value of 36.0 mg KOH/g, and the weight average molecular weight Mw measured by GPC was about 6530.

利用差示掃描量熱術測量玻璃化轉變溫度的結果是-32.1℃。 The result of measuring the glass transition temperature by differential scanning calorimetry was -32.1 °C.

<比較合成例1> <Comparative Synthesis Example 1>

如下合成沒有本申請的化學式1和化學式2化合物的鹼溶性樹脂。 An alkali-soluble resin which does not have the chemical formula 1 and the chemical formula 2 of the present application is synthesized as follows.

向配備攪拌器、恒溫器、回流冷卻管、滴液套組和氮氣引入管的燒瓶添加100g的丙二醇單甲醚乙酸酯和120g的丙二醇單甲醚，並在燒瓶中的氣體從空氣轉換為氮氣後，向其引入3.2g的偶氮雙異丁腈、9.4g的丙烯酸、35.2g的甲基丙烯酸苄酯、55.5g的4-甲基苯乙烯和6.0g的正十二硫醇，並進行氮取代。之後，在攪拌生成物的同時將所述反應溶液的溫度升高到80℃，並將所述生成物反應8小時。如上合成的鹼溶性樹脂的固體酸值為99.2mg KOH/g，並且用GPC測量的重均分子量Mw為大約14560。 To a flask equipped with a stirrer, a thermostat, a reflux cooling tube, a drip set, and a nitrogen introduction tube, 100 g of propylene glycol monomethyl ether acetate and 120 g of propylene glycol monomethyl ether were added, and the gas in the flask was converted from air to After nitrogen, 3.2 g of azobisisobutyronitrile, 9.4 g of acrylic acid, 35.2 g of benzyl methacrylate, 55.5 g of 4-methylstyrene, and 6.0 g of n-dodecylmer were introduced thereto. Perform nitrogen substitution. Thereafter, the temperature of the reaction solution was raised to 80 ° C while stirring the product, and the resultant was reacted for 8 hours. The alkali-soluble resin synthesized as above had a solid acid value of 99.2 mg KOH/g, and the weight average molecular weight Mw measured by GPC was about 14,560.

利用差示掃描量熱術測量玻璃化轉變溫度的結果是98℃。 The result of measuring the glass transition temperature by differential scanning calorimetry was 98 °C.

<比較合成例2> <Comparative Synthesis Example 2>

如下合成沒有本申請的化學式1和化學式2化合物的鹼溶性樹脂。 An alkali-soluble resin which does not have the chemical formula 1 and the chemical formula 2 of the present application is synthesized as follows.

向配備攪拌器、恒溫器、回流冷卻管、滴液套組和氮氣引入管的燒瓶添加100g的丙二醇單甲醚乙酸酯和120g的丙二醇單甲醚，並在燒瓶中的氣體從空氣轉換為氮氣後，向其引入3.2g的偶氮雙異丁腈、9.4g的丙烯酸、35.2g的甲基丙烯酸苄酯、67.3g的4-甲基苯乙烯、10.0g的甲基丙烯酸甲酯和6.0g的正十二硫醇，並進行氮取代。之後，在攪拌生成物的同時將所述反應溶液的溫度升高到80℃，並將所述生成物反應8小時。如上合成的鹼溶性樹脂的固體酸 值為83.2mg KOH/g，並且用GPC測量的重均分子量Mw為大約17305。 To a flask equipped with a stirrer, a thermostat, a reflux cooling tube, a drip set, and a nitrogen introduction tube, 100 g of propylene glycol monomethyl ether acetate and 120 g of propylene glycol monomethyl ether were added, and the gas in the flask was converted from air to After nitrogen, 3.2 g of azobisisobutyronitrile, 9.4 g of acrylic acid, 35.2 g of benzyl methacrylate, 67.3 g of 4-methylstyrene, 10.0 g of methyl methacrylate and 6.0 were introduced thereto. G-dodecyl mercaptan and nitrogen substitution. Thereafter, the temperature of the reaction solution was raised to 80 ° C while stirring the product, and the resultant was reacted for 8 hours. Solid acid of alkali-soluble resin synthesized as above The value was 83.2 mg KOH/g, and the weight average molecular weight Mw measured by GPC was about 17305.

利用差示掃描量熱術測量玻璃化轉變溫度的結果是87℃。 The result of measuring the glass transition temperature by differential scanning calorimetry was 87 °C.

<比較合成例3> <Comparative Synthesis Example 3>

如下合成未使用本申請化學式1和化學式2化合物的鹼溶性樹脂。 An alkali-soluble resin which does not use the chemical formula 1 and the chemical formula 2 of the present application is synthesized as follows.

向配備攪拌器、恒溫器、回流冷卻管、滴液套組和氮氣引入管的燒瓶添加100g的丙二醇單甲醚乙酸酯和120g的丙二醇單甲醚，並在燒瓶中的氣體從空氣轉換為氮氣後，向其引入3.2g的偶氮雙異丁腈、3.6g的丙烯酸、70.4g的甲基丙烯酸苄酯、41.3g的4-甲基苯乙烯、20.0g的甲基丙烯酸甲酯和6.0g的正十二硫醇，並進行氮取代。之後，在攪拌生成物的同時將所述反應溶液的溫度升高到80℃，並將所述生成物反應8小時。如上合成的鹼溶性樹脂的固體酸值為17.2mg KOH/g，並且用GPC測量的重均分子量Mw為大約17702。 To a flask equipped with a stirrer, a thermostat, a reflux cooling tube, a drip set, and a nitrogen introduction tube, 100 g of propylene glycol monomethyl ether acetate and 120 g of propylene glycol monomethyl ether were added, and the gas in the flask was converted from air to After nitrogen, 3.2 g of azobisisobutyronitrile, 3.6 g of acrylic acid, 70.4 g of benzyl methacrylate, 41.3 g of 4-methylstyrene, 20.0 g of methyl methacrylate and 6.0 were introduced thereto. G-dodecyl mercaptan and nitrogen substitution. Thereafter, the temperature of the reaction solution was raised to 80 ° C while stirring the product, and the resultant was reacted for 8 hours. The alkali-soluble resin synthesized as above had a solid acid value of 17.2 mg KOH/g, and the weight average molecular weight Mw measured by GPC was about 17,702.

利用差示掃描量熱術測量玻璃化轉變溫度的結果是80℃。 The result of measuring the glass transition temperature by differential scanning calorimetry was 80 °C.

<比較合成例4> <Comparative Synthesis Example 4>

利用本申請的化學式1化合物(2-降冰片烯)而不使用化學式2化合物，如下合成鹼溶性樹脂。 Using the compound of Chemical Formula 1 (2-norbornene) of the present application without using the compound of Chemical Formula 2, an alkali-soluble resin is synthesized as follows.

向配備攪拌器、恒溫器、回流冷卻管、滴液套組 和氮氣引入管的燒瓶添加100g的丙二醇單甲醚乙酸酯和120g的丙二醇單甲醚，並在燒瓶中的氣體從空氣轉換為氮氣後，向其引入3.2g的偶氮雙異丁腈、9.4g的丙烯酸、9.4g的2-降冰片烯、52.8g的甲基丙烯酸苄酯、43.7g的4-甲基苯乙烯、10.0g的甲基丙烯酸甲酯和6.0g的正十二硫醇，並進行氮取代。之後，在攪拌生成物的同時將所述反應溶液的溫度升高到80℃，並將所述生成物反應8小時。如上合成的鹼溶性樹脂的固體酸值為100.3mg KOH/g，並且用GPC測量的重均分子量Mw為大約15340。利用差示掃描量熱術測量玻璃化轉變溫度的結果是110℃。 Equipped with agitator, thermostat, reflux cooling tube, drip set The flask with the nitrogen introduction tube was charged with 100 g of propylene glycol monomethyl ether acetate and 120 g of propylene glycol monomethyl ether, and after the gas in the flask was converted from air to nitrogen, 3.2 g of azobisisobutyronitrile was introduced thereto. 9.4 g of acrylic acid, 9.4 g of 2-norbornene, 52.8 g of benzyl methacrylate, 43.7 g of 4-methylstyrene, 10.0 g of methyl methacrylate and 6.0 g of n-dodecyl mercaptan And carry out nitrogen substitution. Thereafter, the temperature of the reaction solution was raised to 80 ° C while stirring the product, and the resultant was reacted for 8 hours. The alkali-soluble resin synthesized as above had a solid acid value of 100.3 mg KOH/g, and the weight average molecular weight Mw measured by GPC was about 15340. The result of measuring the glass transition temperature by differential scanning calorimetry was 110 °C.

<比較合成例5> <Comparative Synthesis Example 5>

利用丙烯酸正丁酯作為化學式2化合物而不使用本申請的化學式1化合物，如下合成鹼溶性樹脂。 An alkali-soluble resin is synthesized as follows by using n-butyl acrylate as the chemical formula 2 compound without using the compound of the chemical formula 1 of the present application.

向配備攪拌器、恒溫器、回流冷卻管、滴液套組和氮氣引入管的燒瓶添加150g的丙二醇單甲醚乙酸酯和70g的丙二醇單甲醚，並在燒瓶中的氣體從空氣轉換為氮氣後，向其引入3.2g的偶氮雙異丁腈、9.4g的丙烯酸、51.2g的丙烯酸正丁酯、43.7g的4-甲基苯乙烯、10.0g的甲基丙烯酸甲酯和6.0g的正十二硫醇，並進行氮取代。之後，在攪拌生成物的同時將所述反應溶液的溫度升高到80℃，並將所述生成物反應8小時。如上合成的鹼溶性樹脂的固體酸值為102.0mg KOH/g，並且用GPC測量的重均分子量Mw為大約8760。 To a flask equipped with a stirrer, a thermostat, a reflux cooling tube, a drip set, and a nitrogen introduction tube, 150 g of propylene glycol monomethyl ether acetate and 70 g of propylene glycol monomethyl ether were added, and the gas in the flask was converted from air to After nitrogen, 3.2 g of azobisisobutyronitrile, 9.4 g of acrylic acid, 51.2 g of n-butyl acrylate, 43.7 g of 4-methylstyrene, 10.0 g of methyl methacrylate and 6.0 g were introduced thereto. The n-dodecyl mercaptan is replaced by nitrogen. Thereafter, the temperature of the reaction solution was raised to 80 ° C while stirring the product, and the resultant was reacted for 8 hours. The alkali-soluble resin synthesized as above had a solid acid value of 102.0 mg KOH/g, and the weight average molecular weight Mw measured by GPC was about 8760.

利用差示掃描量熱術測量玻璃化轉變溫度的結 果是-40℃。 Measurement of the glass transition temperature by differential scanning calorimetry The result is -40 ° C.

實施例和比較例Examples and comparative examples

通過以下表1的比率混合著色劑(A)、鹼溶性樹脂(B)、光可聚合性化合物(C)、光聚合引發劑(D)和溶劑(E)，製備實施例和比較例的著色感光樹脂組合物。 The coloring of the examples and comparative examples was prepared by mixing the coloring agent (A), the alkali-soluble resin (B), the photopolymerizable compound (C), the photopolymerization initiator (D), and the solvent (E) in the ratios of Table 1 below. Photosensitive resin composition.

試驗例Test case

試驗例1：製造彩色濾光片以及評價顯影速率和黏合性Test Example 1: Fabrication of color filters and evaluation of development rate and adhesion

(1)製造彩色濾光片 (1) Manufacturing color filters

利用在所述實施例和比較例中製備的著色感光樹脂組合物製造彩色濾光片。 A color filter was produced using the colored photosensitive resin compositions prepared in the above Examples and Comparative Examples.

具體地，各著色感光樹脂組合物利用旋塗法在2英寸見方的玻璃基板(Corning Incorporated製造，「EAGLE XG])上塗層，並將生成物放在加熱板上並在100℃溫度下保持3分鐘以形成薄膜。隨後，具有透射比以步進方式從1至100%改變的圖案和1μm至100μm的線條/空間圖案的試驗光掩模放置在所述薄膜上，在離所述試驗光掩模300μm距離處照射紫外線。在此，使用含有全部g、h和i-射線的1KW高壓汞蒸氣燈作為光源，以60mJ/cm2的強度照射紫外線，沒有使用特殊的濾光片。紫外線照射過的薄膜浸在pH 10.5的KOH水溶液的顯影溶液中2分鐘進行顯影。所述薄膜塗層的玻璃板用蒸餾水洗滌，然後吹氮氣乾燥，並在加熱爐中200℃下加熱25分鐘，以製造彩色濾光片。 Specifically, each of the colored photosensitive resin compositions was coated on a 2 inch square glass substrate (manufactured by Corning Incorporated, "EAGLE XG") by spin coating, and the resultant was placed on a hot plate and kept at a temperature of 100 ° C. 3 minutes to form a film. Subsequently, a test photomask having a transmittance varying from 1 to 100% in a stepwise manner and a line/space pattern of 1 μm to 100 μm was placed on the film, away from the test light The mask was irradiated with ultraviolet rays at a distance of 300 μm. Here, a 1 KW high-pressure mercury vapor lamp containing all g, h, and i-rays was used as a light source, and ultraviolet rays were irradiated at an intensity of 60 mJ/cm 2 without using a special filter. The film was immersed in a developing solution of an aqueous KOH solution of pH 10.5 for 2 minutes for development. The film-coated glass plate was washed with distilled water, then dried with nitrogen, and heated in a heating furnace at 200 ° C for 25 minutes to manufacture. Color filter.

上述製造的彩色濾光片的膜厚度為2.4μm。 The color filter manufactured above had a film thickness of 2.4 μm.

(2)顯影速率評價 (2) Development rate evaluation

利用下面描述的方法評價彩色濾光片的顯影速率。 The development rate of the color filter was evaluated by the method described below.

在上述方法中，測量在顯影期間未曝光部分完全溶解在顯影溶液中所花的時間(顯影速率)並在下面表2中列出。 In the above method, the time (development rate) taken when the unexposed portion was completely dissolved in the developing solution during development was measured and listed in Table 2 below.

(3)黏合性評價 (3) Evaluation of adhesion

利用下面描述的方法評價彩色濾光片的黏合性。 The adhesion of the color filter was evaluated by the method described below.

利用光學顯微鏡觀察所產生的圖案並如下評價20μm圖案撕裂的程度，結果在下面表2中顯示。 The resulting pattern was observed with an optical microscope and the degree of tear of the 20 μm pattern was evaluated as follows, and the results are shown in Table 2 below.

<評價標準> <Evaluation criteria>

○：沒有圖案撕裂 ○: no pattern tearing

△：1至3個圖案撕裂 △: 1 to 3 pattern tears

×：4或更多個圖案撕裂 ×: 4 or more pattern tears

試驗例2：製造彩色濾光片和評價透射率 Test Example 2: Manufacturing a color filter and evaluating transmittance

除了沒有使用試驗光掩模之外，以與試驗例1相同的方式製造彩色濾光片。之後，利用下面描述的方法測量透射率(%)。 A color filter was produced in the same manner as in Test Example 1 except that the test photomask was not used. Thereafter, the transmittance (%) was measured by the method described below.

利用色度計(Olympus Corporation製造，OSP-200)測量所形成的圖案中100μm的線條圖案部分，結果在下面表2中顯示。 A line pattern portion of 100 μm in the formed pattern was measured using a colorimeter (manufactured by Olympus Corporation, OSP-200), and the results are shown in Table 2 below.

試驗例3：製造彩色濾光片和評價耐熱性 Test Example 3: Manufacturing a color filter and evaluating heat resistance

*360以與試驗例1相同的方式製造彩色濾光片。之後，利用下面描述的方法測量耐熱性(△E*ab)。 *360 A color filter was produced in the same manner as in Test Example 1. Thereafter, the heat resistance (ΔE*ab) was measured by the method described below.

關於耐熱性測量，獲得所述彩色濾光片在230℃下留置120分鐘前後的變色值，結果在表2中顯示。 Regarding the heat resistance measurement, the color change value of the color filter before and after leaving at 230 ° C for 120 minutes was obtained, and the results are shown in Table 2.

根據表2，本發明的著色感光樹脂組合物(實施例1至5)即使在很高的顯影速率下仍表現出優異的黏合性，並同時具有高透射率和優異的耐熱性，鑒定了本發明的著色感光樹脂組合物適合於製造高品質彩色濾光片。 According to Table 2, the colored photosensitive resin compositions of the present invention (Examples 1 to 5) exhibited excellent adhesion even at a high development rate, and at the same time, had high transmittance and excellent heat resistance, and the present invention was identified. The inventive colored photosensitive resin composition is suitable for the manufacture of high quality color filters.

特別是，優點在於，25秒或更短的顯影速率是優選的，因為減少了製造彩色濾光片花費的時間；具有3個或更少的圖案撕裂是優選的，因為彩色濾光片的產量增加；13.7或更高的透射率可以導致製造具有高亮度的彩色濾光片；和2.5或更少的耐熱性可以在附加的熱過程中最小化由變色引起的缺陷出現。 In particular, there is an advantage in that a development rate of 25 seconds or shorter is preferable because the time taken to manufacture the color filter is reduced; it is preferable to have 3 or less pattern tears because of the color filter The increase in yield; the transmittance of 13.7 or higher can result in the production of a color filter having high brightness; and the heat resistance of 2.5 or less can minimize the occurrence of defects caused by discoloration in an additional thermal process.

透射率即使在1%的差異下仍然強烈影響彩色濾光片的亮度，因此，改善透射率是代表感光樹脂組合物的品質的很重要的性質，並鑒定了本發明的組合物全部具有與比較例相比透射率改善了3%或更高的優異效應。 The transmittance strongly affects the brightness of the color filter even under the difference of 1%, and therefore, the improvement of the transmittance is a very important property representing the quality of the photosensitive resin composition, and it is identified that all of the compositions of the present invention have and compared. The superior effect of the improvement of 3% or higher was improved compared to the transmittance.

本發明的著色感光樹脂組合物即使在很高的顯影速率下仍表現出優異的黏合性，並具有高透射率和優異 的耐熱性，因此，在製造高品質彩色濾光片中具有合適的優點。 The colored photosensitive resin composition of the present invention exhibits excellent adhesion even at a high development rate, and has high transmittance and excellent The heat resistance, therefore, has suitable advantages in the manufacture of high quality color filters.

Claims (9)

一種著色感光樹脂組合物，其包含：著色劑(A)；鹼溶性樹脂(B)；光可聚合性化合物(C)；光聚合引發劑(D)；和溶劑(E)，其中所述著色劑(A)包含染料，並且所述鹼溶性樹脂(B)包含由下面化學式1和化學式2表示的化合物並具有低於0℃的玻璃化轉變溫度： 在化學式1中，n是0或1，R1和R2各自獨立地是氫、或者包含或不包含C1至C12雜原子的脂族或芳族烴；和R3至R6各自獨立地是氫、或者包含或不包含C1至C30雜原子的脂族或芳族烴，並且R3至R6中的兩個可以聯接形成環；和 在化學式2中，R7獨立地是氫、或者包含或不包含C1至C12雜原子的脂族或芳族烴；和R8是取代或未取代的直鏈或支鏈C2至C30烷基。 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), wherein the coloring The agent (A) contains a dye, and the alkali-soluble resin (B) contains a compound represented by the following Chemical Formula 1 and Chemical Formula 2 and has a glass transition temperature lower than 0 ° C: In Chemical Formula 1, n is 0 or 1, and R 1 and R 2 are each independently hydrogen or an aliphatic or aromatic hydrocarbon having or not containing a C 1 to C 12 hetero atom; and R 3 to R 6 are each independently Is hydrogen or an aliphatic or aromatic hydrocarbon containing or not containing a C 1 to C 30 hetero atom, and two of R 3 to R 6 may be joined to form a ring; In Chemical Formula 2, R 7 is independently hydrogen or an aliphatic or aromatic hydrocarbon containing or not containing a C 1 to C 12 hetero atom; and R 8 is a substituted or unsubstituted linear or branched C 2 to C 30 alkyl. 如請求項1所述的著色感光樹脂組合物，其中化學式1表示的化合物是下列化合物的任一種： The colored photosensitive resin composition according to claim 1, wherein the compound represented by Chemical Formula 1 is any one of the following compounds: 如請求項1所述的著色感光樹脂組合物，其中所述鹼溶性樹脂(B)還包含下面化學式3表示的化合物： 其中，在化學式3中，p是1至100的整數；R9是包含由酸酐衍生的羧酸的殘基；以及R10和R11各自獨立地是氫或甲基。 The colored photosensitive resin composition according to claim 1, wherein the alkali-soluble resin (B) further contains a compound represented by the following Chemical Formula 3: Wherein, in Chemical Formula 3, p is an integer of 1 to 100; R 9 is a residue comprising a carboxylic acid derived from an acid anhydride; and R 10 and R 11 are each independently hydrogen or methyl. 如請求項3所述的著色感光樹脂組合物，其中所述酸酐是選自由鄰苯二甲酸酐、(2-十二烯-1-基)琥珀酸酐、馬來酸酐、琥珀酸酐、檸康酸酐、戊二酸酐、甲基琥珀酸酐、3,3-二甲基戊二酸酐、苯基琥珀酸酐、衣康酸酐、3,4,5,6-四氫鄰苯二甲酸酐、偏苯三酸酐、六氫鄰苯二甲酸酐和降冰片烯二酸酐組成的組中的一種或多種。 The colored photosensitive resin composition according to claim 3, wherein the acid anhydride is selected from the group consisting of phthalic anhydride, (2-dodecen-1-yl) succinic anhydride, maleic anhydride, succinic anhydride, citraconic anhydride , glutaric anhydride, methyl succinic anhydride, 3,3-dimethylglutaric anhydride, phenyl succinic anhydride, itaconic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, trimellitic anhydride, hexahydrogen One or more of the group consisting of phthalic anhydride and norbornene dianhydride. 如請求項1所述的著色感光樹脂組合物，其中相對於100mol%的鹼溶性樹脂(B)，所述鹼溶性樹脂(B)包括2mol%至20mol%的來源於化學式1的單元；2mol%至70mol%的來源於化學式2的構成單元；和10mol%至90mol%的來源於化學式3的構成單元。 The colored photosensitive resin composition according to claim 1, wherein the alkali-soluble resin (B) comprises 2 mol% to 20 mol% of the unit derived from the chemical formula 1 with respect to 100 mol% of the alkali-soluble resin (B); 2 mol% Up to 70 mol% of the constituent unit derived from Chemical Formula 2; and 10 mol% to 90 mol% of the constituent unit derived from Chemical Formula 3. 如請求項1的著色感光樹脂組合物，其包含：基於所述著色感光樹脂組合物的總重量，5重量%至60重量%的所述著色劑(A)；5重量%至80重量%的所述鹼溶性樹脂(B)；1重量%至60重量%的所述光可聚合性化合物(C)；和0.1重量%至40重量%的所述光聚合引發劑(D)；以及60重量%至90重量%的溶劑(E)。 The colored photosensitive resin composition of claim 1, which comprises: 5% by weight to 60% by weight, based on the total weight of the colored photosensitive resin composition, of the coloring agent (A); 5% by weight to 80% by weight The alkali-soluble resin (B); 1% by weight to 60% by weight of the photopolymerizable compound (C); and 0.1% by weight to 40% by weight of the photopolymerization initiator (D); and 60% by weight % to 90% by weight of solvent (E). 如請求項1所述的著色感光樹脂組合物，其還包含選自其他聚合物化合物、固化劑、表面活性劑、黏合性助黏劑、抗氧化劑、紫外線吸收劑和解聚結劑的一種或多種 添加劑。 The colored photosensitive resin composition according to claim 1, which further comprises one or more selected from the group consisting of other polymer compounds, curing agents, surfactants, adhesive adhesion promoters, antioxidants, ultraviolet absorbers, and deagglomerating agents. additive. 一種彩色濾光片，其使用請求項1至7任一項所述的著色感光樹脂組合物製造。 A color filter produced by using the colored photosensitive resin composition according to any one of claims 1 to 7. 一種液晶顯示裝置，其包含請求項8所述的彩色濾光片。 A liquid crystal display device comprising the color filter of claim 8.
TW105105438A 2015-03-13 2016-02-24 Colored photosensitive resin composition, color filter and liquid crystal display device including the color filter TW201638669A (en)

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