TWI843889B - Manufacturing method of red coloring composition for color filter, red coloring composition for color filter, red coloring resist composition for color filter, color filter, and display device - Google Patents
Manufacturing method of red coloring composition for color filter, red coloring composition for color filter, red coloring resist composition for color filter, color filter, and display device Download PDFInfo
- Publication number
- TWI843889B TWI843889B TW109131836A TW109131836A TWI843889B TW I843889 B TWI843889 B TW I843889B TW 109131836 A TW109131836 A TW 109131836A TW 109131836 A TW109131836 A TW 109131836A TW I843889 B TWI843889 B TW I843889B
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- TW
- Taiwan
- Prior art keywords
- color filter
- red coloring
- coloring composition
- resin
- pigment
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 112
- 238000004040 coloring Methods 0.000 title claims abstract description 99
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 33
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- 239000000049 pigment Substances 0.000 claims abstract description 70
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- 125000000542 sulfonic acid group Chemical group 0.000 claims abstract description 17
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims abstract description 14
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- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims abstract description 13
- 238000003801 milling Methods 0.000 claims abstract description 13
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- 238000004898 kneading Methods 0.000 claims abstract description 9
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- 238000001035 drying Methods 0.000 description 4
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- RQGPLDBZHMVWCH-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole Chemical compound C1=NC2=CC=NC2=C1 RQGPLDBZHMVWCH-UHFFFAOYSA-N 0.000 description 4
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
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- 125000001424 substituent group Chemical group 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 2
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- OWPUOLBODXJOKH-UHFFFAOYSA-N 2,3-dihydroxypropyl prop-2-enoate Chemical compound OCC(O)COC(=O)C=C OWPUOLBODXJOKH-UHFFFAOYSA-N 0.000 description 2
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- GTEXIOINCJRBIO-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOCCN(C)C GTEXIOINCJRBIO-UHFFFAOYSA-N 0.000 description 1
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Abstract
本發明提供一種起因於有機顏料之昇華物得到抑制，且能夠獲得對比度及亮度優異之濾色器的濾色器用紅色著色組成物之製造方法。 本發明之濾色器用紅色著色組成物之製造方法具有如下步驟：微粒子化步驟，其係將吡咯并吡咯二酮（diketopyrrolopyrrole）顏料與樹脂、以及吡咯并吡咯二酮化合物之磺化物一起進行鹽磨（salt milling）處理而獲得微粒子化顏料；以及混練融合步驟，其係將包含上述微粒子化顏料、以及具有偶氮基及萘酚骨架之化合物之磺化物的混合物進行混練融合；上述樹脂具有順丁烯二醯亞胺骨架及磺酸基。The present invention provides a method for producing a red coloring composition for a color filter, which can obtain a color filter with excellent contrast and brightness by suppressing the sublimation of organic pigments. The method for producing a red coloring composition for a color filter of the present invention comprises the following steps: a micronization step, which is to obtain micronized pigment by salt milling diketopyrrolopyrrole pigment, resin, and sulfonate of diketopyrrolopyrrole compound; and a kneading and fusing step, which is to knead and fuse a mixture containing the micronized pigment and sulfonate of a compound having an azo group and a naphthol skeleton; the resin having a succinimidyl skeleton and a sulfonic acid group.
Description
本發明係關於一種濾色器用紅色著色組成物之製造方法、濾色器用紅色著色組成物、濾色器用紅色著色阻劑組成物、濾色器、及顯示裝置。The present invention relates to a method for manufacturing a red coloring composition for a color filter, a red coloring composition for a color filter, a red coloring resist composition for a color filter, a color filter, and a display device.
作為實現液晶電視之高畫質化所不可欠缺之技術，有形成高精細濾色器之技術。作為濾色器，有於玻璃等透明基板之表面平行地配置有兩種以上之不同色相之微細帶（條紋）者、或以一定之排列縱橫地配置有微細像素者等。As an indispensable technology for achieving high-definition images of LCD TVs, there is a technology for forming high-precision color filters. As color filters, there are those that have two or more fine stripes (stripes) of different colors arranged in parallel on the surface of a transparent substrate such as glass, or those that have fine pixels arranged vertically and horizontally in a certain arrangement.
像素尺寸為數10～數100 μm之微細之大小，需要將每個色相以特定之順序整齊地排列。進而，對於各色相之像素，作為基本性能，亦要求色純度與可見光之穿透率較高，進而對比度較高。The pixel size is a tiny 10 to 100 μm, and each hue needs to be neatly arranged in a specific order. Furthermore, as a basic performance, the pixels of each hue are also required to have high color purity and visible light transmittance, and thus high contrast.
隨著液晶顯示面板之用途之多樣化，就耐熱性、耐光性等可靠性之方面而言，多使用有機顏料作為像素之有色材料。As the uses of liquid crystal display panels become more diverse, organic pigments are often used as color materials for pixels in terms of reliability such as heat resistance and light resistance.
以往，使用濾色器用紅色顏料分散物，該濾色器用紅色顏料分散物使用C.I.顏料紅242、C.I.顏料紅254或C.I.顏料紅177作為有機顏料（例如專利文獻1）。Conventionally, a red pigment dispersion for a color filter has been used, which uses C.I. Pigment Red 242, C.I. Pigment Red 254, or C.I. Pigment Red 177 as an organic pigment (e.g., Patent Document 1).
然而，於使用C.I.顏料紅254作為有機顏料之情形時，存在產生昇華物而導致亮度或對比度降低之情形，於使用C.I.顏料紅242或C.I.顏料紅177之情形時，存在如下問題：為了使該等有機顏料分散而需要顏料衍生物，起因於此而亮度變得不充分。However, when C.I. Pigment Red 254 is used as an organic pigment, sublimates are produced, resulting in reduced brightness or contrast. When C.I. Pigment Red 242 or C.I. Pigment Red 177 is used, a pigment derivative is required to disperse the organic pigment, resulting in insufficient brightness.
近年來，作為濾色器用有機顏料，溴化吡咯并吡咯二酮顏料受到關注（例如專利文獻2～4）。In recent years, brominated diketopyrrolopyrrole pigments have attracted attention as organic pigments for color filters (e.g., Patent Documents 2 to 4).
然而，即便於溴化吡咯并吡咯二酮顏料中，昇華物亦為成為問題之程度，又，近年來，關於對比度或亮度之要求提高，存在進一步改善之餘地。 [先前技術文獻] [專利文獻]However, even in brominated diketopyrrolopyrrole pigments, sublimates are problematic, and in recent years, demands for contrast and brightness have increased, leaving room for further improvement. [Prior Art Literature] [Patent Literature]
[專利文獻1]日本特開2011-162722號公報 [專利文獻2]日本特開2011-523433號公報 [專利文獻3]日本特開2012-155232號公報 [專利文獻4]日本特開2018-158962號公報[Patent Document 1] Japanese Patent Publication No. 2011-162722 [Patent Document 2] Japanese Patent Publication No. 2011-523433 [Patent Document 3] Japanese Patent Publication No. 2012-155232 [Patent Document 4] Japanese Patent Publication No. 2018-158962
[發明所欲解決之課題][The problem that the invention wants to solve]
本發明鑒於上述課題，其目的在於提供一種起因於有機顏料之昇華物得到抑制，且能夠獲得對比度及亮度優異之濾色器的濾色器用紅色著色組成物之製造方法。 [解決課題之技術手段]In view of the above-mentioned problem, the present invention aims to provide a method for manufacturing a red coloring composition for a color filter, which can suppress the sublimation of organic pigments and obtain a color filter with excellent contrast and brightness. [Technical means for solving the problem]
本發明人等鑒於上述課題，反覆進行深入研究，結果發現藉由濾色器用紅色著色組成物之製造方法，能夠獲得可解決上述所有課題之濾色器用紅色著色組成物，從而完成了本發明，上述濾色器用紅色著色組成物之製造方法具有如下步驟：微粒子化步驟，其係將吡咯并吡咯二酮（diketopyrrolopyrrole）顏料與具有順丁烯二醯亞胺骨架及磺酸基之樹脂、以及吡咯并吡咯二酮化合物之磺化物一起進行鹽磨（salt milling）處理而獲得微粒子化顏料；以及混練融合步驟，其係將包含上述微粒子化顏料、以及具有偶氮基及萘酚骨架之化合物之磺化物的混合物進行混練融合。In view of the above-mentioned problems, the inventors of the present invention have repeatedly conducted in-depth research and found that a method for producing a red coloring composition for a color filter that can solve all the above-mentioned problems can be obtained, thereby completing the present invention. The method for producing the red coloring composition for a color filter has the following steps: a micronization step, which is to salt mill a diketopyrrolopyrrole pigment, a resin having a succinimide skeleton and a sulfonic acid group, and a sulfonate of a diketopyrrolopyrrole compound to obtain a micronized pigment; and a kneading and fusing step, which is to knead and fuse a mixture containing the above-mentioned micronized pigment and a sulfonate of a compound having an azo group and a naphthol skeleton.
即，本發明之濾色器用紅色著色組成物之製造方法具有如下步驟：微粒子化步驟，其係將吡咯并吡咯二酮顏料與樹脂、以及吡咯并吡咯二酮化合物之磺化物一起進行鹽磨處理而獲得微粒子化顏料；以及混練融合步驟，其係將包含上述微粒子化顏料、以及具有偶氮基及萘酚骨架之化合物之磺化物的混合物進行混練融合；上述樹脂具有順丁烯二醯亞胺骨架及磺酸基。That is, the method for producing the red coloring composition for a color filter of the present invention comprises the following steps: a micronization step, in which a pyrrolopyrrole diketo pigment is subjected to salt milling treatment together with a resin and a sulfonate of a pyrrolopyrrole diketo compound to obtain a micronized pigment; and a kneading and fusing step, in which a mixture containing the micronized pigment and a sulfonate of a compound having an azo group and a naphthol skeleton is kneaded and fused; the resin having a succinimidyl skeleton and a sulfonic acid group.
本發明之濾色器用紅色著色組成物之製造方法中，上述吡咯并吡咯二酮系顏料較佳為具有溴基。 上述樹脂較佳為具有源自苯基順丁烯二醯亞胺之重複單元。 上述樹脂之磺酸值較佳為0.1～20 mgKOH/g。 本發明亦為藉由上述濾色器用紅色著色組成物之製造方法所獲得之濾色器用紅色著色組成物。 本發明亦為由上述濾色器用紅色著色組成物所獲得之濾色器用紅色著色阻劑組成物。 又，本發明亦為由上述濾色器用紅色著色阻劑組成物所形成之濾色器。 又，本發明亦為包含上述濾色器之顯示裝置。 以下，詳細地說明本發明之濾色器用紅色著色組成物之製造方法、濾色器用紅色著色組成物、濾色器用紅色著色阻劑組成物、濾色器、及顯示裝置。In the method for producing the red coloring composition for color filters of the present invention, the above-mentioned diketopyrrolopyrrole pigment preferably has a bromine group. The above-mentioned resin preferably has a repeating unit derived from phenyl cis-butylene diimide. The sulfonic acid value of the above-mentioned resin is preferably 0.1 to 20 mgKOH/g. The present invention is also a red coloring composition for color filters obtained by the method for producing the red coloring composition for color filters. The present invention is also a red coloring resistor composition for color filters obtained from the above-mentioned red coloring composition for color filters. In addition, the present invention is also a color filter formed by the above-mentioned red coloring resistor composition for color filters. Furthermore, the present invention is also a display device including the above-mentioned color filter. The following describes in detail the manufacturing method of the red coloring composition for the color filter, the red coloring composition for the color filter, the red coloring resist composition for the color filter, the color filter, and the display device of the present invention.
＜濾色器用紅色著色組成物之製造方法＞ 本發明之濾色器用紅色著色組成物之製造方法具有如下步驟：微粒子化步驟，其係將吡咯并吡咯二酮顏料與樹脂、以及吡咯并吡咯二酮化合物之磺化物一起進行鹽磨處理而獲得微粒子化顏料；以及混練融合步驟，其係將包含上述微粒子化顏料、以及具有偶氮基及萘酚骨架之化合物之磺化物的混合物進行混練融合；上述樹脂具有順丁烯二醯亞胺骨架及磺酸基。<Method for producing a red coloring composition for a color filter> The method for producing a red coloring composition for a color filter of the present invention comprises the following steps: a micronization step, which is to obtain micronized pigment by salt-milling a pyrrolopyrrole diketo pigment, a resin, and a sulfonate of a pyrrolopyrrole diketo compound; and a kneading and fusing step, which is to knead and fuse a mixture containing the micronized pigment and a sulfonate of a compound having an azo group and a naphthol skeleton; the resin having a succinimidyl skeleton and a sulfonic acid group.
[微粒子化步驟] 上述微粒子化步驟係將吡咯并吡咯二酮顏料與樹脂、以及吡咯并吡咯二酮化合物之磺化物一起進行鹽磨處理而獲得微粒子化顏料之步驟。 首先，對上述微粒子化步驟中使用之吡咯并吡咯二酮顏料、樹脂、以及吡咯并吡咯二酮化合物之磺化物進行說明。[Microparticle formation step] The microparticle formation step is a step of obtaining microparticles by salt-milling the diketopyrrolopyrrole pigment, the resin, and the sulfonate of the diketopyrrolopyrrole compound. First, the diketopyrrolopyrrole pigment, the resin, and the sulfonate of the diketopyrrolopyrrole compound used in the microparticle formation step are described.
（吡咯并吡咯二酮系顏料） 作為上述吡咯并吡咯二酮系顏料，例如可列舉下述通式（1）所表示之化合物。(Diketopyrrolopyrrole pigments) As the above-mentioned diketopyrrolopyrrole pigments, for example, compounds represented by the following general formula (1) can be cited.
上述通式（1）中，X表示氫原子、氯原子或溴原子，A及B分別獨立為氫原子、氟原子、氯原子、溴原子、碘原子、氰基、碳數1～12之烷基、可具有取代基之苯基、-CF3 、-OR1 、-SR2 、-N(R3 )R4 、-COOR5 、-CONH2 、-CONHR6 、-CON(R7 )R8 、-SO2 NH2 、-SO2 NHR9 、或-SO2 N(R10 )R11 ，R1 ～R11 分別獨立為碳數1～12之烷基、可具有取代基之苯基、或可具有取代基之芳烷基。In the above general formula (1), X represents a hydrogen atom, a chlorine atom or a bromine atom, A and B are independently a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, an alkyl group having 1 to 12 carbon atoms, a phenyl group which may have a substituent, -CF3 , -OR1 , -SR2 , -N( R3 ) R4 , -COOR5 , -CONH2 , -CONHR6 , -CON( R7 ) R8 , -SO2NH2 , -SO2NHR9 , or -SO2N ( R10 ) R11 , and R1 to R11 are independently an alkyl group having 1 to 12 carbon atoms, a phenyl group which may have a substituent, or an aralkyl group which may have a substituent.
作為上述吡咯并吡咯二酮系顏料之市售品，例如可列舉C.I.顏料紅254、255、264、272、291、C.I.顏料橙71、73或81等。Examples of commercially available diketopyrrolopyrrole pigments include C.I. Pigment Red 254, 255, 264, 272, 291, and C.I. Pigment Orange 71, 73, or 81.
就適當提高對比度及亮度，適當抑制昇華物之觀點而言，上述吡咯并吡咯二酮系顏料較佳為具有溴基。 作為上述具有溴基之吡咯并吡咯二酮系顏料，例如可列舉下述化學式所表示之化合物，作為其市售品，可列舉C.I.顏料紅291。From the viewpoint of appropriately improving contrast and brightness and appropriately suppressing sublimation products, the above-mentioned diketopyrrolopyrrole pigment preferably has a bromine group. As the above-mentioned diketopyrrolopyrrole pigment having a bromine group, for example, the compound represented by the following chemical formula can be listed, and as its commercially available product, C.I. Pigment Red 291 can be listed.
以濾色器用紅色著色組成物之總質量為基準，上述吡咯并吡咯二酮系顏料之含量較佳為5～20質量%，更佳為7～16質量%。 藉由以上述範圍含有上述吡咯并吡咯二酮系顏料，能夠適當提高使用濾色器用紅色著色組成物所獲得之濾色器之對比度及亮度。Based on the total mass of the red coloring composition for the color filter, the content of the above-mentioned diketopyrrolopyrrole pigment is preferably 5 to 20 mass%, and more preferably 7 to 16 mass%. By containing the above-mentioned diketopyrrolopyrrole pigment in the above-mentioned range, the contrast and brightness of the color filter obtained by using the red coloring composition for the color filter can be appropriately improved.
於以上述範圍含有上述吡咯并吡咯二酮系顏料之情形時，亦可併用其他紅色顏料。 作為上述其他紅色顏料，可列舉C.I.顏料紅177、242等。 作為上述其他紅色顏料之含量，例如以上述吡咯并吡咯二酮系顏料之含量為基準，為1～50質量%。 就抑制起因於有機顏料之昇華物之觀點、適當提高使用濾色器用紅色著色組成物所獲得之濾色器之對比度及亮度之觀點而言，較佳為不含有上述其他紅色顏料。When the above-mentioned diketopyrrolopyrrole pigment is contained in the above-mentioned range, other red pigments may be used in combination. As the above-mentioned other red pigments, C.I. Pigment Red 177, 242, etc. can be listed. As the content of the above-mentioned other red pigments, for example, based on the content of the above-mentioned diketopyrrolopyrrole pigment, it is 1 to 50 mass %. From the viewpoint of suppressing sublimation products caused by organic pigments and appropriately improving the contrast and brightness of the filter obtained by using the red coloring composition for the filter, it is preferred not to contain the above-mentioned other red pigments.
（樹脂） 上述樹脂具有順丁烯二醯亞胺骨架及磺酸基。 上述樹脂例如可藉由使乙烯基單體、具有順丁烯二醯亞胺骨架之單體、以及具有磺酸基之單體共聚而獲得。(Resin) The resin has a succinimidyl skeleton and a sulfonic acid group. The resin can be obtained, for example, by copolymerizing a vinyl monomer, a monomer having a succinimidyl skeleton, and a monomer having a sulfonic acid group.
作為上述乙烯基單體，例如可列舉：(甲基)丙烯酸、(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸丙酯、(甲基)丙烯酸異丙酯、(甲基)丙烯酸丁酯、(甲基)丙烯酸第二丁酯、(甲基)丙烯酸異丁酯、(甲基)丙烯酸第三丁酯、(甲基)丙烯酸環己酯、(甲基)丙烯酸2-乙基己酯、(甲基)丙烯酸苄酯、乙酸乙烯酯、丙酸乙烯酯、丁酸乙烯酯、戊酸乙烯酯（vinyl valerate）、苯乙烯、氯丁二烯、氯乙烯、偏二氯乙烯、丙烯腈、1-丁烯、丁二烯、甲基丙烯腈、乙烯基甲苯、乙烯基***、甲基丙烯酸全氟己基乙基-硫代-羰基-胺基乙基酯、甲基丙烯酸異莰酯（isobornyl methacrylate）、甲基丙烯酸三氟乙酯、甲基丙烯酸六氟異丙酯、甲基丙烯酸六氟丁酯、含矽氧烷之乙烯基單體等。 其中，較佳為(甲基)丙烯酸、(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸丙酯、(甲基)丙烯酸異丙酯、(甲基)丙烯酸丁酯、(甲基)丙烯酸第二丁酯、(甲基)丙烯酸異丁酯、(甲基)丙烯酸第三丁酯、(甲基)丙烯酸環己酯、(甲基)丙烯酸2-乙基己酯、(甲基)丙烯酸苄酯，就與微粒子化步驟或混練融合步驟時使用之介質之親和性、或獲得之樹脂之諸物性之觀點而言，更佳為(甲基)丙烯酸、(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸丙酯、(甲基)丙烯酸異丙酯、(甲基)丙烯酸丁酯、(甲基)丙烯酸苄酯。 上述乙烯基單體可使用一種或併用兩種以上而使用。 再者，本說明書中，(甲基)丙烯酸意指丙烯酸及甲基丙烯酸。Examples of the vinyl monomer include (meth)acrylic acid, methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, isopropyl (meth)acrylate, butyl (meth)acrylate, sec-butyl (meth)acrylate, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, benzyl (meth)acrylate, vinyl acetate, vinyl propionate, vinyl butyrate, vinyl valerate, styrene, chloroprene, vinyl chloride, vinylidene chloride, acrylonitrile, 1-butene, butadiene, methacrylonitrile, vinyl toluene, ethyl vinyl ether, perfluorohexylethyl-thio-carbonyl-aminoethyl methacrylate, isobornyl methacrylate, methacrylate), trifluoroethyl methacrylate, hexafluoroisopropyl methacrylate, hexafluorobutyl methacrylate, silicone-containing vinyl monomers, etc. Among them, preferred are (meth)acrylic acid, methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, isopropyl (meth)acrylate, butyl (meth)acrylate, sec-butyl (meth)acrylate, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, benzyl (meth)acrylate. From the perspective of affinity with the medium used in the micronization step or the kneading and fusion step, or the physical properties of the obtained resin, more preferred are (meth)acrylic acid, methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, isopropyl (meth)acrylate, butyl (meth)acrylate, and benzyl (meth)acrylate. The above-mentioned vinyl monomers can be used alone or in combination of two or more. In addition, in this specification, (meth)acrylic acid means acrylic acid and methacrylic acid.
作為上述具有順丁烯二醯亞胺骨架之單體，例如可列舉：N-環己基順丁烯二醯亞胺、N-苯基順丁烯二醯亞胺、N-甲基順丁烯二醯亞胺、N-乙基順丁烯二醯亞胺、N-異丙基順丁烯二醯亞胺、N-第三丁基順丁烯二醯亞胺、N-十二烷基順丁烯二醯亞胺、N-苄基順丁烯二醯亞胺、N-萘基順丁烯二醯亞胺等。 其中，就適當抑制起因於有機顏料之昇華物之觀點而言，較佳為N-苯基順丁烯二醯亞胺。 上述具有順丁烯二醯亞胺骨架之單體可使用一種或併用兩種以上而使用。Examples of the monomer having a cis-butenediamide skeleton include: N-cyclohexyl cis-butenediamide, N-phenyl cis-butenediamide, N-methyl cis-butenediamide, N-ethyl cis-butenediamide, N-isopropyl cis-butenediamide, N-tert-butyl cis-butenediamide, N-dodecyl cis-butenediamide, N-benzyl cis-butenediamide, N-naphthyl cis-butenediamide, etc. Among them, N-phenyl cis-butenediamide is preferred from the viewpoint of appropriately suppressing sublimation products derived from organic pigments. The above-mentioned monomers having a cis-butylenediimide skeleton may be used alone or in combination of two or more.
作為上述具有磺酸基之單體，例如可列舉：(甲基)丙烯醯胺烷磺酸、乙烯基磺酸、(甲基)丙烯醯胺第三丁基磺酸及苯乙烯磺酸等。 其中，就適當抑制起因於有機顏料之昇華物之觀點、適當提高使用濾色器用紅色著色組成物所獲得之濾色器之對比度之觀點而言，較佳為丙烯醯胺第三丁基磺酸。 上述具有磺酸基之單體可使用一種或併用兩種以上而使用。Examples of the monomer having a sulfonic acid group include (meth)acrylamide alkanesulfonic acid, vinylsulfonic acid, (meth)acrylamide tert-butylsulfonic acid, and styrenesulfonic acid. Among them, from the viewpoint of appropriately suppressing sublimation products caused by organic pigments and appropriately improving the contrast of the filter obtained by using the red coloring composition for the filter, acrylamide tert-butylsulfonic acid is preferred. The monomer having a sulfonic acid group can be used alone or in combination of two or more.
使上述乙烯基單體、上述具有順丁烯二醯亞胺骨架之單體、以及上述具有磺酸基之單體共聚時的質量比如下所述。 以上述單體之合計含量（質量）為基準，上述乙烯基單體較佳為40～80質量%，更佳為50～70質量%。 以上述單體之合計含量為基準，上述具有順丁烯二醯亞胺骨架之單體較佳為10～50質量%，更佳為20～40質量%。 以上述單體之合計含量為基準，上述具有磺酸基之單體較佳為1～10質量%，更佳為2.5～5質量%。 藉由以上述範圍使上述乙烯基單體、上述具有順丁烯二醯亞胺骨架之單體、以及上述具有磺酸基之單體共聚，能夠適當抑制起因於有機顏料之昇華物，又，能夠適當提高使用濾色器用紅色著色組成物所獲得之濾色器之對比度。The mass ratio of the above-mentioned vinyl monomer, the above-mentioned monomer having a succinimidyl skeleton, and the above-mentioned monomer having a sulfonic acid group when copolymerized is as follows. Based on the total content (mass) of the above-mentioned monomers, the above-mentioned vinyl monomer is preferably 40 to 80 mass%, and more preferably 50 to 70 mass%. Based on the total content of the above-mentioned monomers, the above-mentioned monomer having a succinimidyl skeleton is preferably 10 to 50 mass%, and more preferably 20 to 40 mass%. Based on the total content of the above-mentioned monomers, the above-mentioned monomer having a sulfonic acid group is preferably 1 to 10 mass%, and more preferably 2.5 to 5 mass%. By copolymerizing the vinyl monomer, the monomer having a succinimide skeleton, and the monomer having a sulfonic acid group within the above range, sublimation products derived from organic pigments can be appropriately suppressed, and the contrast of a filter obtained using the red coloring composition for a filter can be appropriately improved.
使上述乙烯基單體、上述具有順丁烯二醯亞胺骨架之單體、以及上述具有磺酸基之單體共聚之方法並無特別限定，可使用公知之共聚等方法。The method for copolymerizing the vinyl monomer, the monomer having a cis-butylenediimide skeleton, and the monomer having a sulfonic acid group is not particularly limited, and a known copolymerization method can be used.
上述樹脂較佳為具有源自苯基順丁烯二醯亞胺之重複單元。 藉由上述樹脂具有源自苯基順丁烯二醯亞胺之重複單元，能夠適當抑制起因於有機顏料之昇華物。 藉由包含N-苯基順丁烯二醯亞胺作為上述具有順丁烯二醯亞胺骨架之單體，能夠獲得具有源自苯基順丁烯二醯亞胺之重複單元之樹脂。The above-mentioned resin preferably has a repeating unit derived from phenyl cis-butylene diimide. By having the above-mentioned resin having a repeating unit derived from phenyl cis-butylene diimide, sublimation products caused by organic pigments can be appropriately suppressed. By including N-phenyl cis-butylene diimide as the above-mentioned monomer having a cis-butylene diimide skeleton, a resin having a repeating unit derived from phenyl cis-butylene diimide can be obtained.
上述樹脂之磺酸值較佳為0.1～20 mgKOH/g。 藉由上述樹脂之磺酸值為上述範圍，能夠適當抑制起因於有機顏料之昇華物，又，能夠適當提高使用濾色器用紅色著色組成物所獲得之濾色器之對比度。 上述樹脂之磺酸值更佳為6～18 mgKOH/g，進而較佳為8～14 mgKOH/g。 藉由將使上述乙烯基單體、上述具有順丁烯二醯亞胺骨架之單體、以及上述具有磺酸基之單體共聚時的上述具有磺酸基之單體之質量比設為上述範圍，能夠適當調整上述樹脂之磺酸值。 再者，上述磺酸值係指以毫克數計算出中和樹脂1 g中所含之磺酸所需之氫氧化鉀之量所得之理論值。The sulfonic acid value of the resin is preferably 0.1 to 20 mgKOH/g. When the sulfonic acid value of the resin is within the above range, sublimation products caused by organic pigments can be appropriately suppressed, and the contrast of the filter obtained by using the red coloring composition for the filter can be appropriately improved. The sulfonic acid value of the resin is more preferably 6 to 18 mgKOH/g, and further preferably 8 to 14 mgKOH/g. The sulfonic acid value of the resin can be appropriately adjusted by setting the mass ratio of the monomer having a sulfonic acid group when copolymerizing the vinyl monomer, the monomer having a succinimide skeleton, and the monomer having a sulfonic acid group to the above range. The above sulfonic acid value refers to the theoretical value calculated in milligrams as the amount of potassium hydroxide required to neutralize the sulfonic acid contained in 1 g of the resin.
就樹脂自身之製造性、或與微粒子化步驟時使用之介質之親和性之觀點而言，上述樹脂之重量平均分子量較佳為1000～10000，更佳為2000～5000，進而較佳為2500～4000。 再者，作為上述重量平均分子量，可使上述樹脂溶解而製作0.02質量%之溶液，使其通過過濾器（GL Science公司製造，GL層析盤，水系25 A，孔徑0.2 μm）後，使用由粒徑篩析層析儀、折射率檢測器構成之alliance（Nihon Waters公司製造），根據以下條件進行測定。 管柱：pLgel mixed D（安捷倫公司製造）×2根 串聯連接 檢測器：alliance（Nihon Waters公司製造） 溶離液：THF 流速：1.0 ml/min 注入量：100 μlFrom the viewpoint of the manufacturability of the resin itself or the affinity with the medium used in the micronization step, the weight average molecular weight of the above resin is preferably 1000 to 10000, more preferably 2000 to 5000, and further preferably 2500 to 4000. In addition, as the above weight average molecular weight, the above resin can be dissolved to prepare a 0.02 mass % solution, which is passed through a filter (GL Science, GL chromatography disk, water system 25 A, pore size 0.2 μm), and then measured using alliance (Nihon Waters) consisting of a particle size screening chromatography instrument and a refractive index detector under the following conditions. Column: pLgel mixed D (manufactured by Agilent) × 2 connected in series Detector: alliance (manufactured by Nihon Waters) Eluent: THF Flow rate: 1.0 ml/min Injection volume: 100 μl
以濾色器用紅色著色組成物之總質量為基準，上述樹脂之含量較佳為0.1～5質量%，更佳為0.5～3質量%。Based on the total mass of the red coloring composition for the filter, the content of the above resin is preferably 0.1-5 mass %, more preferably 0.5-3 mass %.
（吡咯并吡咯二酮化合物之磺化物） 上述微粒子化步驟中使用吡咯并吡咯二酮化合物之磺化物。 藉由使用上述吡咯并吡咯二酮化合物之磺化物，能夠適當提高使用濾色器用紅色著色組成物所獲得之濾色器之對比度及亮度。(Sulfonated product of diketopyrrolopyrrole compound) The sulfonated product of diketopyrrolopyrrole compound is used in the micronization step. By using the sulfonated product of diketopyrrolopyrrole compound, the contrast and brightness of the filter obtained by using the red coloring composition for the filter can be appropriately improved.
作為上述吡咯并吡咯二酮化合物之磺化物，可列舉：C.I.顏料紅254、255、264、272及291、C.I.顏料橙71及73等之磺化物。 其中，就進一步適當提高使用濾色器用紅色著色組成物所獲得之濾色器之對比度及亮度之觀點而言，較佳為C.I.顏料橙71之磺化物。As the sulfonated product of the above-mentioned diketopyrrolopyrrole compound, there can be listed: sulfonated products of C.I. Pigment Red 254, 255, 264, 272 and 291, C.I. Pigment Orange 71 and 73, etc. Among them, from the viewpoint of further appropriately improving the contrast and brightness of the filter obtained by using the filter red coloring composition, the sulfonated product of C.I. Pigment Orange 71 is preferred.
使上述吡咯并吡咯二酮化合物磺化之方法並無特別限定，可使用公知之方法。The method for sulfonating the diketopyrrolopyrrole compound is not particularly limited, and a known method can be used.
以濾色器用紅色著色組成物之總質量為基準，上述吡咯并吡咯二酮化合物之磺化物之含量較佳為0.1～5質量%，更佳為0.5～3質量%。 藉由以上述範圍含有上述吡咯并吡咯二酮化合物之磺化物，能夠進一步適當提高使用濾色器用紅色著色組成物所獲得之濾色器之對比度及亮度兩者。Based on the total mass of the red coloring composition for the filter, the content of the sulfonated diketopyrrolopyrrole compound is preferably 0.1 to 5 mass%, and more preferably 0.5 to 3 mass%. By containing the sulfonated diketopyrrolopyrrole compound in the above range, the contrast and brightness of the filter obtained by using the red coloring composition for the filter can be further appropriately improved.
（鹽磨處理） 作為上述鹽磨處理，例如可使用以下方法。 於上述吡咯并吡咯二酮顏料、上述樹脂及上述吡咯并吡咯二酮化合物之磺化物中添加無機鹽、有機溶劑後，一面加熱一面混練而進行鹽磨。 其後，將接下來獲得之混練物投入至溫水中，一面加熱一面攪拌而形成漿料狀。其後，反覆進行過濾及洗淨，去除無機鹽及有機溶劑後進行乾燥。(Salt milling treatment) As the above-mentioned salt milling treatment, for example, the following method can be used. After adding an inorganic salt and an organic solvent to the above-mentioned diketopyrrolopyrrole pigment, the above-mentioned resin, and the above-mentioned sulfonated product of the diketopyrrolopyrrole compound, the mixture is kneaded while being heated to perform salt milling. Thereafter, the kneaded product obtained is added to warm water, and is stirred while being heated to form a slurry. Thereafter, filtering and washing are repeated to remove the inorganic salt and the organic solvent, and then drying is performed.
作為上述無機鹽，較佳為使用水溶性無機鹽，例如較佳為使用氯化鈉、氯化鉀、硫酸鈉等。 作為上述無機鹽，更佳為使用一次粒徑0.5～50 μm之無機鹽。 上述無機鹽之使用量相對於上述吡咯并吡咯二酮顏料1質量份，較佳為設為3～20質量份，更佳為設為5～15質量份。As the above-mentioned inorganic salt, it is preferred to use a water-soluble inorganic salt, for example, it is preferred to use sodium chloride, potassium chloride, sodium sulfate, etc. As the above-mentioned inorganic salt, it is more preferred to use an inorganic salt with a primary particle size of 0.5 to 50 μm. The amount of the above-mentioned inorganic salt used is preferably set to 3 to 20 parts by mass, and more preferably set to 5 to 15 parts by mass relative to 1 part by mass of the above-mentioned diketopyrrolopyrrole pigment.
作為上述鹽磨處理中使用之有機溶劑，較佳為使用能夠抑制有機顏料之結晶生長之有機溶劑。 作為此種有機溶劑，例如可使用二乙二醇、甘油、乙二醇、丙二醇、液體聚乙二醇、液體聚丙二醇、2-(甲氧基甲氧基)乙醇、2-丁氧基乙醇、2-(異戊氧基)乙醇、2-(己氧基)乙醇、二乙二醇單甲醚、二乙二醇單***、二乙二醇單丁醚、三乙二醇、三乙二醇單甲醚、1-甲氧基-2-丙醇、1-乙氧基-2-丙醇、二丙二醇、二丙二醇單甲醚、二丙二醇單甲醚、二丙二醇等。As the organic solvent used in the above-mentioned salt milling treatment, it is preferred to use an organic solvent that can inhibit the crystal growth of the organic pigment. As such an organic solvent, for example, diethylene glycol, glycerol, ethylene glycol, propylene glycol, liquid polyethylene glycol, liquid polypropylene glycol, 2-(methoxymethoxy)ethanol, 2-butoxyethanol, 2-(isopentyloxy)ethanol, 2-(hexyloxy)ethanol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, triethylene glycol, triethylene glycol monomethyl ether, 1-methoxy-2-propanol, 1-ethoxy-2-propanol, dipropylene glycol, dipropylene glycol monomethyl ether, dipropylene glycol monomethyl ether, dipropylene glycol, etc. can be used.
作為上述鹽磨處理中使用之混練機，可列舉：捏合機、二輥研磨機、三輥研磨機、行星式混合機等。Examples of the kneading machine used in the above-mentioned salt milling treatment include a kneader, a two-roll mill, a three-roll mill, a planetary mixer, and the like.
上述鹽磨處理中混練時之溫度較佳為30～150℃。混練時間較佳為2小時至20小時。The mixing temperature in the salt milling treatment is preferably 30 to 150° C. The mixing time is preferably 2 to 20 hours.
上述鹽磨處理後之洗淨可採用水洗、熱水洗之任一者。又，亦可使用酸、鹼或溶劑。 上述洗淨亦可反覆進行1～5次之範圍。 只要使用水溶性無機鹽作為上述無機鹽，使用水溶性有機溶劑作為有機溶劑，則可藉由上述洗淨容易去除水溶性無機鹽及水溶性有機溶劑。The washing after the salt grinding treatment can be done by water washing or hot water washing. Alternatively, an acid, an alkali or a solvent can be used. The above washing can also be repeated 1 to 5 times. As long as a water-soluble inorganic salt is used as the above inorganic salt and a water-soluble organic solvent is used as the organic solvent, the water-soluble inorganic salt and the water-soluble organic solvent can be easily removed by the above washing.
上述乾燥例如可藉由設置於乾燥機之加熱源加熱至80～120℃等，可使用批次式乾燥方法或連續式乾燥方法。作為上述乾燥機，可使用箱型乾燥機、帶式乾燥機、噴霧乾燥器等。The drying can be performed by heating to 80 to 120° C. using a heat source installed in the dryer, for example, and a batch drying method or a continuous drying method can be used. As the dryer, a box dryer, a belt dryer, a spray dryer, etc. can be used.
[混練融合步驟] 上述混練融合步驟係將包含上述微粒子化顏料、及具有偶氮基及萘酚骨架之化合物之磺化物的混合物進行混練融合之步驟。[Mixing and fusing step] The above-mentioned mixing and fusing step is a step of mixing and fusing a mixture containing the above-mentioned micronized pigment and a sulfonated product of a compound having an azo group and a naphthol skeleton.
（具有偶氮基及萘酚骨架之化合物之磺化物） 上述混練融合步驟中使用具有偶氮基及萘酚骨架之化合物之磺化物。 藉由使用上述具有偶氮基及萘酚骨架之化合物，能夠適當提高使用濾色器用紅色著色組成物所獲得之濾色器之亮度，又，提高上述吡咯并吡咯二酮系顏料之分散性，提高使用濾色器用紅色著色組成物所獲得之濾色器之對比度。(Sulfonated compound having an azo group and a naphthol skeleton) The sulfonated compound having an azo group and a naphthol skeleton is used in the above kneading and fusing step. By using the above compound having an azo group and a naphthol skeleton, the brightness of the filter obtained by using the red coloring composition for the filter can be appropriately improved, and the dispersibility of the above diketopyrrolopyrrole pigment can be improved, and the contrast of the filter obtained by using the red coloring composition for the filter can be improved.
作為上述具有偶氮基及萘酚骨架之化合物，可列舉C.I.顏料紅2、112、188、C.I.顏料棕25等。 上述具有偶氮基及萘酚骨架之化合物之磺化物可藉由使上述具有偶氮基及萘酚骨架的化合物磺化而獲得。 作為磺化之方法並無特別限定，可使用公知之方法。 其中，就進一步適當提高使用濾色器用紅色著色組成物所獲得之濾色器之亮度之觀點而言，較佳為C.I.顏料紅188之磺化物，就適當提高有機顏料之分散穩定性，提高使用濾色器用紅色著色組成物所獲得之濾色器之對比度之觀點而言，較佳為C.I.顏料紅2之磺化物。As the above-mentioned compound having an azo group and a naphthol skeleton, C.I. Pigment Red 2, 112, 188, C.I. Pigment Brown 25, etc. can be listed. The sulfonated product of the above-mentioned compound having an azo group and a naphthol skeleton can be obtained by sulfonating the above-mentioned compound having an azo group and a naphthol skeleton. The sulfonation method is not particularly limited, and a known method can be used. Among them, from the viewpoint of further appropriately improving the brightness of the filter obtained using the red coloring composition for the filter, the sulfonated product of C.I. Pigment Red 188 is preferred, and from the viewpoint of appropriately improving the dispersion stability of the organic pigment and improving the contrast of the filter obtained using the red coloring composition for the filter, the sulfonated product of C.I. Pigment Red 2 is preferred.
以濾色器用紅色著色組成物之總質量為基準，上述具有偶氮基及萘酚骨架之化合物之磺化物的含量較佳為0.1～5質量%，更佳為0.5～3質量%。Based on the total mass of the red coloring composition for the filter, the content of the sulfonated compound having an azo group and a naphthol skeleton is preferably 0.1 to 5 mass %, more preferably 0.5 to 3 mass %.
上述混合物較佳為包含顏料分散劑、鹼可溶性樹脂以及有機溶劑。The mixture preferably comprises a pigment dispersant, an alkali-soluble resin and an organic solvent.
（顏料分散劑） 作為上述顏料分散劑，例如可列舉：日本特開平3-277673號公報、日本特開平10-339949號公報、日本特表2003-517063號公報等中記載之主鏈具有醯胺系骨架、側鏈由源自甲基丙烯酸酯之巨單體所構成之接枝聚合物；日本特開平7-96654號公報、日本特開平7-207178號公報等中記載之具有脂肪族羥基羧酸殘基之聚酯系低聚物；有機矽氧烷聚合物（KP341等，信越化學工業公司製造）；(甲基)丙烯酸系(共)聚合物（Polyflow No.75、90、95等，共榮油脂化學工業公司製造）；陽離子系界面活性劑（W001等，裕商公司製造）；聚氧乙烯月桂醚、聚氧乙烯硬脂醚、聚氧乙烯油醚、聚氧乙烯辛基苯醚、聚氧乙烯壬基苯醚、聚乙二醇二月桂酸酯、聚乙二醇二硬脂酸酯、山梨醇酐脂肪酸酯等非離子系界面活性劑；陰離子系界面活性劑（W004、W005、W017等，裕商公司製造）；作為其他市售品，可列舉：Solsperse 3000、5000、9000、12000、13240、13940、17000、20000、24000、26000、28000等（Zeneca公司製造）各種Solsperse分散劑；Ajisper PB-821、PB-822（Ajinomoto Fine-Techno公司製造）；IONET S-20（三洋化成公司製造）；Disperbyk-160、161、162、163、164、182、184、BYK-LPN23590、BYK-LPN6919、BYK-LPN21116、BYK-LPN21234（BYK Chemie公司製造）；EFKA-46、47、48等（EFKA Chemicals BV公司製造）。 該等之中，就微細穩定化之觀點而言，較佳為主鏈具有醯胺系骨架、側鏈由源自甲基丙烯酸酯之巨單體所構成之接枝聚合物，具體而言，較佳為主鏈含有乙烯吡咯啶酮（vinylpyrrolidone）、側鏈由甲基丙烯酸甲酯之巨單體所構成之接枝聚合物。 上述顏料分散劑可使用一種或併用兩種以上而使用。(Pigment dispersant) As the above-mentioned pigment dispersant, for example, there can be listed: a graft polymer having an amide backbone in the main chain and a macromonomer derived from methacrylate in the side chain as described in Japanese Patent Publication No. 3-277673, Japanese Patent Publication No. 10-339949, Japanese Patent Publication No. 2003-517063, etc.; a polyester oligomer having aliphatic hydroxycarboxylic acid residues as described in Japanese Patent Publication No. 7-96654, Japanese Patent Publication No. 7-207178, etc.; an organosiloxane polymer (KP341, etc., manufactured by Shin-Etsu Chemical Co., Ltd.); a (meth)acrylic (co)polymer (Polyflow No.75, 90, 95, etc., manufactured by Gongrong Oil and Chemical Industry Co., Ltd.); cationic surfactants (W001, etc., manufactured by Yu Shang Co., Ltd.); non-ionic surfactants such as polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene oleyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene nonylphenyl ether, polyethylene glycol dilaurate, polyethylene glycol distearate, sorbitan fatty acid ester; anionic surfactants (W004, W005, W017, etc., manufactured by Yu Shang Co., Ltd.); other commercially available products include: Solsperse 3000, 5000, 9000, 12000, 13240, 13940, 17000, 20000, 24000, 26000, 28000, etc. (manufactured by Zeneca) various Solsperse dispersants; Ajisper PB-821, PB-822 (manufactured by Ajinomoto Fine-Techno); IONET S-20 (manufactured by Sanyo Chemical); Disperbyk-160, 161, 162, 163, 164, 182, 184, BYK-LPN23590, BYK-LPN6919, BYK-LPN21116, BYK-LPN21234 (manufactured by BYK Chemie); EFKA-46, 47, 48, etc. (manufactured by EFKA Chemicals BV). Among them, from the viewpoint of micro-stabilization, a graft polymer having an amide skeleton in the main chain and a side chain composed of a macromonomer derived from methacrylate is preferred. Specifically, a graft polymer having vinylpyrrolidone in the main chain and a side chain composed of a macromonomer of methyl methacrylate is preferred. The above-mentioned pigment dispersants can be used alone or in combination of two or more.
以濾色器用紅色著色組成物之總質量為基準，上述顏料分散劑之含量較佳為1～10質量%，更佳為2～8質量%。Based on the total mass of the red coloring composition for the color filter, the content of the pigment dispersant is preferably 1 to 10 mass %, more preferably 2 to 8 mass %.
（鹼可溶性樹脂） 作為上述鹼可溶性樹脂，只要為於製造濾色器時，對其顯影處理步驟中使用之顯影液、鹼性顯影液具有可溶性者，則並無特別限定。 其中，作為上述鹼可溶性樹脂，較佳為具有羧基之鹼可溶性樹脂，尤佳為具有1個以上之羧基之乙烯性不飽和單體與其他可共聚之乙烯性不飽和單體的共聚物。 又，只要為對鹼性顯影液具有可溶性者，亦可使用上述共聚所得者，即上述乙烯基單體、上述具有順丁烯二醯亞胺骨架之單體、以及上述具有磺酸基之單體的共聚。(Alkali-soluble resin) The alkali-soluble resin is not particularly limited as long as it is soluble in the developer or alkaline developer used in the development process of the color filter. Among them, the alkali-soluble resin is preferably an alkali-soluble resin having a carboxyl group, and is particularly preferably a copolymer of an ethylenically unsaturated monomer having one or more carboxyl groups and other copolymerizable ethylenically unsaturated monomers. In addition, as long as it is soluble in an alkaline developer, the copolymer obtained by the above-mentioned copolymerization, that is, the copolymer of the above-mentioned vinyl monomer, the above-mentioned monomer having a succinimide skeleton, and the above-mentioned monomer having a sulfonic acid group can also be used.
作為上述具有1個以上之羧基之乙烯性不飽和單體與其他可共聚之乙烯性不飽和單體的共聚物，具體而言，可列舉丙烯酸、甲基丙烯酸等具有羧基之乙烯性不飽和單體、與選自由可與具有羧基之乙烯性不飽和單體共聚之苯乙烯、丙烯酸2-羥基乙酯、甲基丙烯酸2-羥基乙酯、丙烯酸烯丙酯、甲基丙烯酸烯丙酯、丙烯酸苄酯、甲基丙烯酸苄酯、丙烯酸環己酯、甲基丙烯酸環己酯、單丙烯酸甘油酯、甲基丙烯酸甘油酯、N-苯基順丁烯二醯亞胺、聚苯乙烯巨單體及聚甲基丙烯酸甲酯巨單體所組成之群中之至少一種乙烯性不飽和單體之共聚物。Specific examples of the copolymers of the ethylenically unsaturated monomer having one or more carboxyl groups and other copolymerizable ethylenically unsaturated monomers include copolymers of ethylenically unsaturated monomers having carboxyl groups such as acrylic acid and methacrylic acid, and at least one ethylenically unsaturated monomer selected from the group consisting of styrene, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, allyl acrylate, allyl methacrylate, benzyl acrylate, benzyl methacrylate, cyclohexyl acrylate, cyclohexyl methacrylate, glyceryl monoacrylate, glyceryl methacrylate, N-phenylbutylene diimide, polystyrene macromonomers, and polymethyl methacrylate macromonomers copolymerizable with the ethylenically unsaturated monomer having carboxyl groups.
上述共聚物之酸值較佳為50～300 mgKOH/g。於該情形時，若酸值未達50 mgKOH/g，則於使用本發明之著色組成物作為阻劑組成物之情形時，有對鹼性顯影液之溶解性降低之傾向。另一方面，若超過300 mgKOH/g，則有如下傾向：對鹼性顯影液之溶解性過大，於利用鹼性顯影液進行顯影時，容易導致著色層自基板之脫落或著色層表面之膜粗糙。 再者，上述共聚物之酸值可利用電位差滴定法（JIS K 0070：1992）測定。The acid value of the copolymer is preferably 50 to 300 mgKOH/g. In this case, if the acid value is less than 50 mgKOH/g, when the coloring composition of the present invention is used as a resist composition, the solubility in the alkaline developer tends to decrease. On the other hand, if it exceeds 300 mgKOH/g, there is a tendency that the solubility in the alkaline developer is too large, and when developing with the alkaline developer, it is easy to cause the coloring layer to fall off from the substrate or the film on the surface of the coloring layer to be rough. Furthermore, the acid value of the copolymer can be measured by the potentiometric titration method (JIS K 0070: 1992).
上述鹼可溶性樹脂之重量平均分子量通常較佳為1,000～10萬。若鹼可溶性樹脂之重量平均分子量未達1,000，則存在對鹼性顯影液之溶解性提高而顯影特性降低之情形。另一方面，若超過10萬，則存在如下情形：對有機溶劑之溶解性降低，於使用本發明之著色組成物作為阻劑組成物之情形時，黏度變高。 再者，上述鹼可溶性樹脂之重量平均分子量可利用與上述樹脂之重量平均分子量相同之方法測定。The weight average molecular weight of the above-mentioned alkali-soluble resin is generally preferably 1,000 to 100,000. If the weight average molecular weight of the alkali-soluble resin is less than 1,000, the solubility in the alkaline developer increases and the developing characteristics decrease. On the other hand, if it exceeds 100,000, the solubility in the organic solvent decreases, and when the coloring composition of the present invention is used as a resist composition, the viscosity increases. Furthermore, the weight average molecular weight of the above-mentioned alkali-soluble resin can be measured by the same method as the weight average molecular weight of the above-mentioned resin.
上述鹼可溶性樹脂之含量以濾色器用紅色著色組成物之總質量為基準，較佳為5～50質量%。The content of the alkali-soluble resin is preferably 5 to 50% by mass based on the total mass of the red coloring composition for the filter.
（有機溶劑） 作為上述有機溶劑，較佳為常壓（1.013×102 kPa）下之沸點為100～220℃之酯系有機溶劑、醚系有機溶劑、醚酯系有機溶劑、酮系有機溶劑、芳香族烴溶劑及含氮系有機溶劑等。(Organic Solvent) Preferred organic solvents include ester organic solvents, ether organic solvents, ether ester organic solvents, ketone organic solvents, aromatic hydrocarbon solvents and nitrogen-containing organic solvents having a boiling point of 100 to 220 °C at normal pressure (1.013×10 2 kPa).
上述有機溶劑中，就溶解性、顏料分散性、塗佈性等變良好之方面而言，更佳為二乙二醇二甲醚、二乙二醇甲基乙基醚、乙二醇單甲醚乙酸酯、丙二醇單甲醚乙酸酯、丙二醇單***乙酸酯、環己酮、2-庚酮、2-羥基丙酸乙酯、丙酸3-甲基-3-甲氧基丁酯、3-甲氧基丙酸乙酯、3-乙氧基丙酸甲酯、甲酸正戊酯等，進而較佳為丙二醇單甲醚乙酸酯。 上述有機溶劑可使用一種或併用兩種以上而使用。Among the above organic solvents, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, cyclohexanone, 2-heptanone, ethyl 2-hydroxypropionate, 3-methyl-3-methoxybutyl propionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, n-pentyl formate, etc. are more preferred in terms of solubility, pigment dispersibility, coating properties, etc., and propylene glycol monomethyl ether acetate is further preferred. The above organic solvents can be used alone or in combination of two or more.
就上述鹼可溶性樹脂之溶解性、顏料分散性、塗佈性等變良好之方面而言，以濾色器用紅色著色組成物之總質量為基準，上述有機溶劑之含量較佳為30～80質量%，更佳為35～75質量%。In order to improve the solubility, pigment dispersibility, and coating properties of the alkali-soluble resin, the content of the organic solvent is preferably 30 to 80% by mass, more preferably 35 to 75% by mass, based on the total mass of the red coloring composition for the filter.
（混練融合步驟） 上述混練融合步驟中將包含上述各種成分之混合物進行混練融合。 上述混練融合方法並無特別限定，例如使用珠磨機、Ready Mill、超音波均質機、高壓均質機、塗料振盪機、球磨機、輥磨機、砂磨機、砂研磨機、DYNO-MILL、Dispermat、SC-MILL、Nanomizer等，利用公知之方法進行混練融合即可。(Mixing and fusing step) In the above-mentioned mixing and fusing step, the mixture containing the above-mentioned various components is mixed and fused. The above-mentioned mixing and fusing method is not particularly limited, for example, a bead mill, a ready mill, an ultrasonic homogenizer, a high-pressure homogenizer, a coating oscillator, a ball mill, a roller mill, a sand mill, a sand grinder, a DYNO-MILL, a Dispermat, a SC-MILL, a Nanomizer, etc., can be used to mix and fuse using a known method.
＜濾色器用紅色著色組成物＞ 本發明亦為一種藉由上述濾色器用紅色著色組成物之製造方法所獲得之濾色器用紅色著色組成物。 本發明之濾色器用紅色著色組成物藉由上述本發明之濾色器用紅色著色組成物之製造方法而獲得，因此起因於有機顏料之昇華物得到抑制，且能夠獲得對比度及亮度優異之濾色器。<Red coloring composition for color filter> The present invention is also a red coloring composition for color filter obtained by the above-mentioned method for manufacturing the red coloring composition for color filter. The red coloring composition for color filter of the present invention is obtained by the above-mentioned method for manufacturing the red coloring composition for color filter of the present invention, so that the sublimation products of the organic pigment are suppressed, and a color filter with excellent contrast and brightness can be obtained.
＜濾色器用紅色著色阻劑組成物＞ 本發明亦為一種由上述濾色器用紅色著色組成物獲得之濾色器用紅色著色阻劑組成物。 作為本發明之濾色器用紅色著色阻劑組成物，可藉由除上述濾色器用紅色著色組成物以外，添加鹼可溶性樹脂、光聚合性化合物、光聚合起始劑、有機溶劑、及視需要之添加劑等而獲得。<Red coloring resist composition for color filter> The present invention is also a red coloring resist composition for color filter obtained from the above-mentioned red coloring resist composition for color filter. The red coloring resist composition for color filter of the present invention can be obtained by adding an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, an organic solvent, and an additive as required, etc., in addition to the above-mentioned red coloring resist composition for color filter.
（濾色器用紅色著色組成物） 本發明之濾色器用紅色著色阻劑組成物含有上述本發明之濾色器用紅色著色組成物。 以本發明之濾色器用紅色著色阻劑組成物之總質量為基準，上述濾色器用紅色著色組成物之含量較佳為30～80質量%，更佳為40～75質量%。(Red coloring composition for color filter) The red coloring resist composition for color filter of the present invention contains the above-mentioned red coloring composition for color filter of the present invention. Based on the total mass of the red coloring resist composition for color filter of the present invention, the content of the above-mentioned red coloring composition for color filter is preferably 30-80 mass%, and more preferably 40-75 mass%.
（鹼可溶性樹脂） 作為上述鹼可溶性樹脂，可適當選擇上述濾色器用紅色著色組成物之製造方法中記載之鹼可溶性樹脂而使用。(Alkali-soluble resin) As the above-mentioned alkali-soluble resin, the alkali-soluble resin described in the above-mentioned method for producing the red coloring composition for the color filter can be appropriately selected and used.
以本發明之濾色器用紅色著色阻劑組成物之總質量為基準，上述鹼可溶性樹脂之含量較佳為1～35質量%，更佳為3～30質量%。Based on the total mass of the red coloring resist composition for color filters of the present invention, the content of the alkali-soluble resin is preferably 1 to 35 mass %, more preferably 3 to 30 mass %.
（光聚合性化合物） 作為上述光聚合性化合物，可列舉分子內具有1個以上之光聚合性不飽和鍵之單體、低聚物等。光聚合性不飽和鍵係指下述光聚合起始劑能夠利用藉由紫外線或電子束等活性能量線分解時產生之自由基或陽離子之作用進行聚合的不飽和鍵。(Photopolymerizable compound) As the above-mentioned photopolymerizable compound, there can be listed monomers, oligomers, etc. having one or more photopolymerizable unsaturated bonds in the molecule. The photopolymerizable unsaturated bond refers to an unsaturated bond that can be polymerized by the action of free radicals or cations generated when the photopolymerization initiator described below is decomposed by active energy rays such as ultraviolet rays or electron beams.
作為上述分子內具有1個光聚合性不飽和鍵之單體，可例示：(甲基)丙烯酸甲酯、(甲基)丙烯酸丁酯、甲基丙烯酸2-乙基己酯、丙烯酸甲酯、丙烯酸丁酯、丙烯酸2-乙基己酯等甲基丙烯酸烷基酯或丙烯酸烷基酯；甲基丙烯酸苄酯、丙烯酸苄酯等甲基丙烯酸芳烷基酯或丙烯酸芳烷基酯；甲基丙烯酸丁氧基乙酯、丙烯酸丁氧基乙酯等甲基丙烯酸烷氧基烷基酯或丙烯酸烷氧基烷基酯；甲基丙烯酸N,N-二甲基胺基乙酯、丙烯酸N,N-二甲基胺基乙酯等甲基丙烯酸胺基烷基酯或丙烯酸胺基烷基酯；二乙二醇***、三乙二醇丁醚、二丙二醇甲醚等聚伸烷基二醇烷基醚之甲基丙烯酸酯或丙烯酸酯；六乙二醇苯醚等聚伸烷基二醇芳醚之甲基丙烯酸酯或丙烯酸酯；甲基丙烯酸異莰酯或丙烯酸異莰酯；甲基丙烯酸甘油酯或丙烯酸甘油酯；甲基丙烯酸2-羥基乙酯或丙烯酸2-羥基乙酯等。 本說明書中，(甲基)丙烯酸酯意指丙烯酸酯及甲基丙烯酸酯。Examples of the monomer having one photopolymerizable unsaturated bond in the above-mentioned molecule include: alkyl methacrylates or alkyl acrylates such as methyl (meth)acrylate, butyl (meth)acrylate, 2-ethylhexyl methacrylate, methyl acrylate, butyl acrylate, 2-ethylhexyl acrylate; aralkyl methacrylates or aralkyl acrylates such as benzyl methacrylate and benzyl acrylate; alkoxyalkyl methacrylates or alkoxyalkyl acrylates such as butoxyethyl methacrylate and butoxyethyl acrylate; Methacrylates or acrylates such as N,N-dimethylaminoethyl ether, N,N-dimethylaminoethyl acrylate, etc.; methacrylates or acrylates of polyalkylene glycol alkyl ethers such as diethylene glycol ethyl ether, triethylene glycol butyl ether, and dipropylene glycol methyl ether; methacrylates or acrylates of polyalkylene glycol aromatic ethers such as hexaethylene glycol phenyl ether; isoborneol methacrylate or isoborneol acrylate; glyceryl methacrylate or glyceryl acrylate; 2-hydroxyethyl methacrylate or 2-hydroxyethyl acrylate, etc. In this specification, (meth)acrylate means acrylate and methacrylate.
作為上述分子內具有2個以上之光聚合性不飽和鍵之單體，可列舉：雙酚A二甲基丙烯酸酯、1,4-丁二醇二甲基丙烯酸酯、1,3-丁二醇二甲基丙烯酸酯、二乙二醇二甲基丙烯酸酯、二甲基丙烯酸甘油酯、新戊二醇二甲基丙烯酸酯、聚乙二醇二甲基丙烯酸酯、聚丙二醇二甲基丙烯酸酯、四乙二醇二甲基丙烯酸酯、三羥甲基丙烷三甲基丙烯酸酯、新戊四醇三甲基丙烯酸酯、新戊四醇四甲基丙烯酸酯、二新戊四醇四甲基丙烯酸酯、二新戊四醇六甲基丙烯酸酯、二新戊四醇五甲基丙烯酸酯、雙酚A二丙烯酸酯、1,4-丁二醇二丙烯酸酯、1,3-丁二醇二丙烯酸酯、二乙二醇二丙烯酸酯、二丙烯酸甘油酯、新戊二醇二丙烯酸酯、聚乙二醇二丙烯酸酯、聚丙二醇二丙烯酸酯、四乙二醇二丙烯酸酯、三羥甲基丙烷三丙烯酸酯、新戊四醇三丙烯酸酯、新戊四醇四丙烯酸酯、二新戊四醇四丙烯酸酯、二新戊四醇六丙烯酸酯、二新戊四醇五丙烯酸酯等。 上述光聚合性化合物可使用一種或併用兩種以上而使用。Examples of the monomer having two or more photopolymerizable unsaturated bonds in the above-mentioned molecule include bisphenol A dimethacrylate, 1,4-butanediol dimethacrylate, 1,3-butanediol dimethacrylate, diethylene glycol dimethacrylate, glycerol dimethacrylate, neopentyl glycol dimethacrylate, polyethylene glycol dimethacrylate, polypropylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, trihydroxymethylpropane trimethacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate, dipentaerythritol tetramethacrylate, Acid ester, dipentatriol hexamethacrylate, dipentatriol pentamethacrylate, bisphenol A diacrylate, 1,4-butanediol diacrylate, 1,3-butanediol diacrylate, diethylene glycol diacrylate, glycerol diacrylate, neopentyl glycol diacrylate, polyethylene glycol diacrylate, polypropylene glycol diacrylate, tetraethylene glycol diacrylate, trihydroxymethylpropane triacrylate, neopentatriol triacrylate, neopentatriol tetraacrylate, dipentatriol tetraacrylate, dipentatriol hexaacrylate, dipentatriol pentaacrylate, etc. The above-mentioned photopolymerizable compounds can be used alone or in combination of two or more.
以本發明之濾色器用紅色著色阻劑組成物之總質量為基準，上述光聚合性化合物之含量較佳為0.5～20質量%，更佳為1～10質量%。Based on the total mass of the red coloring resist composition for color filters of the present invention, the content of the photopolymerizable compound is preferably 0.5 to 20 mass %, more preferably 1 to 10 mass %.
（光聚合起始劑） 作為上述光聚合起始劑，只要為藉由照射紫外線或電子束等活性能量線而能夠產生自由基或陽離子者，則並無特別限定，例如可列舉：二苯甲酮、N,N'-四乙基-4,4'-二胺基二苯甲酮、4-甲氧基-4'-二甲基胺基二苯甲酮、二苯基乙二酮、2,2-二乙氧基苯乙酮、安息香、安息香甲醚、安息香異丁醚、二苯乙二酮二甲基縮酮（benzil dimethyl ketal）、α-羥基異丁基苯酮、9-氧硫𠮿（thioxanthone）、2-氯-9-氧硫𠮿、1-羥基環己基苯基酮、第三丁基蒽醌、1-氯蒽醌、2,3-二氯蒽醌、3-氯-2-甲基蒽醌、2-乙基蒽醌、1,4-萘醌、1,2-苯并蒽醌、1,4-二甲基蒽醌、2-苯基蒽醌、2-甲基-1[4-(甲硫基)苯基]-2-啉基丙烷-1-酮、三系光聚合起始劑等。 上述光聚合起始劑可使用一種或併用兩種以上而使用。(Photopolymerization initiator) The photopolymerization initiator is not particularly limited as long as it is capable of generating free radicals or cations by irradiation with active energy rays such as ultraviolet rays or electron beams. Examples thereof include benzophenone, N,N'-tetraethyl-4,4'-diaminobenzophenone, 4-methoxy-4'-dimethylaminobenzophenone, diphenylethanedione, 2,2-diethoxyacetophenone, benzoin, benzoin methyl ether, benzoin isobutyl ether, benzil dimethyl ketal, α-hydroxyisobutylbenzophenone, 9-thiothiophenone, （thioxanthone）, 2-chloro-9-oxothiophene , 1-hydroxycyclohexyl phenyl ketone, tert-butyl anthraquinone, 1-chloroanthraquinone, 2,3-dichloroanthraquinone, 3-chloro-2-methylanthraquinone, 2-ethylanthraquinone, 1,4-naphthoquinone, 1,2-benzanthraquinone, 1,4-dimethylanthraquinone, 2-phenylanthraquinone, 2-methyl-1[4-(methylthio)phenyl]-2- 1-Phenylpropane-1-one, tri The photopolymerization initiator may be used alone or in combination of two or more.
以本發明之濾色器用紅色著色阻劑組成物之總質量為基準，上述光聚合起始劑之含量較佳為0.1～5質量%，更佳為0.5～3質量%。Based on the total weight of the red coloring resist composition for color filters of the present invention, the content of the photopolymerization initiator is preferably 0.1 to 5 weight %, more preferably 0.5 to 3 weight %.
（有機溶劑） 作為上述有機溶劑，可適當選擇上述濾色器用紅色著色組成物之製造方法中記載之有機溶劑而使用。(Organic solvent) As the above-mentioned organic solvent, the organic solvent described in the above-mentioned method for producing the red coloring composition for the color filter can be appropriately selected and used.
以本發明之濾色器用紅色著色阻劑組成物之總質量為基準，上述有機溶劑之含量較佳為1～40質量%，更佳為5～35質量%。Based on the total mass of the red coloring resist composition for color filters of the present invention, the content of the organic solvent is preferably 1 to 40 mass %, more preferably 5 to 35 mass %.
（其他添加劑） 本發明之濾色器用紅色著色阻劑組成物可於不損害本發明之效果之範圍內含有添加劑。 作為上述添加劑，可列舉熱聚合抑制劑、矽烷偶合劑、鈦酸酯偶合劑、紫外線吸收劑及抗氧化劑等各種添加劑。(Other additives) The red coloring resist composition for the color filter of the present invention may contain additives within the range that does not impair the effect of the present invention. As the above-mentioned additives, various additives such as thermal polymerization inhibitors, silane coupling agents, titanium ester coupling agents, ultraviolet absorbers and antioxidants can be listed.
（濾色器用紅色著色阻劑組成物之製造方法） 本發明之濾色器用紅色著色阻劑組成物之製造方法並無特別限定，可藉由含有上述材料，利用公知之方法進行混合並混練融合而獲得。(Manufacturing method of red coloring resist composition for color filter) The manufacturing method of the red coloring resist composition for color filter of the present invention is not particularly limited, and can be obtained by mixing and kneading the above-mentioned materials using a known method.
（濾色器用紅色著色阻劑組成物） 本發明之濾色器用紅色著色阻劑組成物之色度x＝0.6400、y＝0.3290時之對比度較佳為6200以上，更佳為6500以上，進而較佳為6800以上，尤佳為7000以上，最佳為7100以上，上述色度係使用分光光度計（島津製作所公司製造，UV-2500PC，C光源2°視野）測定塗膜所得之值，上述塗膜係使用旋轉塗佈機將本發明之濾色器用紅色著色阻劑組成物塗佈於玻璃基板上，於100℃預烘烤3分鐘後，藉由高壓水銀燈進行曝光，於230℃後烘烤30分鐘而得。 再者，上述對比度為將空白組設為10000時之值。(Red coloring resist composition for color filter) When the chromaticity of the red coloring resist composition for color filter of the present invention is x=0.6400 and y=0.3290, the contrast is preferably 6200 or more, more preferably 6500 or more, further preferably 6800 or more, particularly preferably 7000 or more, and most preferably 7100 or more. The above chromaticity is obtained by using a spectrophotometer. The value obtained by measuring the coating with a UV-2500PC meter (manufactured by Shimadzu Corporation, C light source 2° field of view). The above coating is obtained by coating the filter red color resist composition of the present invention on a glass substrate using a rotary coater, pre-baking at 100°C for 3 minutes, exposing with a high-pressure mercury lamp, and post-baking at 230°C for 30 minutes. In addition, the above contrast is the value when the blank group is set to 10000.
本發明之濾色器用紅色著色阻劑組成物之色度x＝0.6400、y＝0.3290時之亮度Y較佳為22.5以上，更佳為22.7以上，進而較佳為22.8以上，上述色度係使用分光光度計（島津製作所公司製造，UV-2500PC，C光源2°視野）測定塗膜所得之值，上述塗膜係使用旋轉塗佈機將本發明之濾色器用紅色著色阻劑組成物塗佈於玻璃基板上，於100℃預烘烤3分鐘後，藉由高壓水銀燈進行曝光，於230℃後烘烤30分鐘而得。The brightness Y of the red coloring resist composition for color filters of the present invention when the chromaticity x=0.6400 and y=0.3290 is preferably 22.5 or more, more preferably 22.7 or more, and further preferably 22.8 or more. The above chromaticity is a value obtained by measuring the coating using a spectrophotometer (manufactured by Shimadzu Corporation, UV-2500PC, C light source 2° field of view). The above coating is obtained by coating the red coloring resist composition for color filters of the present invention on a glass substrate using a rotary coater, pre-baking at 100°C for 3 minutes, exposing by a high-pressure mercury lamp, and post-baking at 230°C for 30 minutes.
＜濾色器＞ 本發明亦為一種由上述濾色器用紅色著色阻劑組成物形成之濾色器。 本發明之濾色器具備紅色濾光片段、綠色濾光片段、及藍色濾光片段，其中之紅色濾光片段由本發明之濾色器用紅色著色阻劑組成物形成。 作為上述綠色濾光片段及上述藍色濾光片段，可藉由公知之材料及方法形成。 本發明之濾色器例如可適當選擇印刷法或光微影法等公知之方法使用。<Color filter> The present invention is also a color filter formed by the above-mentioned red coloring resist composition for color filters. The color filter of the present invention has a red filter segment, a green filter segment, and a blue filter segment, wherein the red filter segment is formed by the red coloring resist composition for color filters of the present invention. The above-mentioned green filter segment and the above-mentioned blue filter segment can be formed by known materials and methods. The color filter of the present invention can be used by, for example, appropriately selecting a known method such as printing or photolithography.
＜顯示裝置＞ 本發明亦為一種包含上述濾色器之顯示裝置。 作為本發明之顯示裝置，只要包含上述本發明之濾色器，則並無特別限定，可列舉公知之液晶顯示裝置或觸控面板等。 [發明之效果]<Display device> The present invention is also a display device including the color filter mentioned above. As the display device of the present invention, there is no particular limitation as long as it includes the color filter of the present invention, and examples thereof include a known liquid crystal display device or a touch panel. [Effect of the invention]
本發明可提供一種起因於有機顏料之昇華物得到抑制，且能夠獲得對比度及亮度優異之濾色器的濾色器用紅色著色組成物之製造方法。The present invention provides a method for producing a red coloring composition for a color filter, which can suppress sublimation products caused by organic pigments and obtain a color filter with excellent contrast and brightness.
以下列舉實施例進一步詳細地說明本發明，但本發明並不僅限定於該等實施例。再者，只要無特別說明，「%」表示「質量%」，「份」表示「質量份」。The present invention is further described in detail with reference to the following examples, but the present invention is not limited to these examples. In addition, unless otherwise specified, "%" means "mass %" and "part" means "mass part".
實施例及比較例中使用之材料如下所述。The materials used in the Examples and Comparative Examples are as follows.
＜有機顏料＞ （PR291） C.I.顏料紅291 （PR254） C.I.顏料紅254 （PR177） C.I.顏料紅177 （PR242） C.I.顏料紅242＜Organic pigment＞ (PR291) C.I. Pigment Red 291 (PR254) C.I. Pigment Red 254 (PR177) C.I. Pigment Red 177 (PR242) C.I. Pigment Red 242
＜磺化物＞ （PR188S） 於100 ml錐形燒瓶中添加濃硫酸30 ml，一面藉由磁力攪拌器進行攪拌，一面投入10 g C.I.顏料紅188，於室溫攪拌30分鐘。於1 L燒杯中放入50 g水與50 g冰之混合物，將上述反應物注入至該冰水中，藉由磁力攪拌器攪拌30分鐘。將其於減壓下過濾、水洗，使所獲得之固體乾燥，獲得PR188S。 （PO71S） 於上述PR188S之製造方法中，將C.I.顏料紅188變更為C.I.顏料橙71，除此以外，藉由相同之方法獲得PO71S。<Sulfonated product> (PR188S) Add 30 ml of concentrated sulfuric acid to a 100 ml conical flask, add 10 g of C.I. Pigment Red 188 while stirring with a magnetic stirrer, and stir at room temperature for 30 minutes. Put a mixture of 50 g of water and 50 g of ice in a 1 L beaker, pour the above reactants into the ice water, and stir with a magnetic stirrer for 30 minutes. Filter and wash with water under reduced pressure, and dry the obtained solid to obtain PR188S. (PO71S) In the above-mentioned method for producing PR188S, except that C.I. Pigment Red 188 is replaced with C.I. Pigment Orange 71, PO71S is obtained by the same method.
＜樹脂＞ （樹脂1） 藉由公知之方法使甲基丙烯酸丁酯（50質量份）、甲基丙烯酸（5質量份）、N-苯基順丁烯二醯亞胺（40質量份）以及丙烯醯胺第三丁基磺酸（5質量份）進行無規共聚，獲得樹脂1。 樹脂1之磺酸值為14 mgKOH/g，重量平均分子量為3000。 （樹脂2） 藉由公知之方法使甲基丙烯酸丁酯（90質量份）、甲基丙烯酸（5質量份）以及丙烯醯胺第三丁基磺酸（5質量份）進行無規共聚，獲得樹脂2。 樹脂2之磺酸值為14 mgKOH/g，重量平均分子量為3000。 （樹脂3） 藉由公知之方法使甲基丙烯酸丁酯（55質量份）、甲基丙烯酸（5質量份）以及N-苯基順丁烯二醯亞胺（40質量份）進行無規共聚，獲得樹脂3。 樹脂3之磺酸值為0 mgKOH/g，重量平均分子量為3000。 再者，上述樹脂1～3之磺酸值係指以毫克數計算出中和樹脂1 g中所含之磺酸所需之氫氧化鉀之量所得之理論值。 又，上述重量平均分子量係使上述樹脂溶解而製作0.02質量%之溶液，使其通過過濾器（GL Science公司製造，GL層析盤，水系25 A，孔徑0.2 μm）後，使用由粒徑篩析層析儀、折射率檢測器構成之alliance（Nihon Waters公司製造），根據以下條件進行測定。 管柱：pLgel mixed D（安捷倫公司製造）×2根 串聯連接 檢測器：alliance（Nihon Waters公司製造） 溶離液：THF 流速：1.0 ml/min 注入量：100 μl<Resin> (Resin 1) Butyl methacrylate (50 parts by mass), methacrylic acid (5 parts by mass), N-phenylbutylene diimide (40 parts by mass) and acrylamide tert-butyl sulfonic acid (5 parts by mass) were randomly copolymerized by a known method to obtain Resin 1. The sulfonic acid value of Resin 1 was 14 mgKOH/g and the weight average molecular weight was 3000. (Resin 2) Butyl methacrylate (90 parts by mass), methacrylic acid (5 parts by mass) and acrylamide tert-butyl sulfonic acid (5 parts by mass) were randomly copolymerized by a known method to obtain Resin 2. The sulfonic acid value of Resin 2 was 14 mgKOH/g and the weight average molecular weight was 3000. (Resin 3) Butyl methacrylate (55 parts by mass), methacrylic acid (5 parts by mass) and N-phenylbutylene diimide (40 parts by mass) were randomly copolymerized by a known method to obtain Resin 3. The sulfonic acid value of Resin 3 is 0 mgKOH/g and the weight average molecular weight is 3000. In addition, the sulfonic acid values of the above-mentioned Resins 1 to 3 refer to the theoretical values calculated in milligrams of the amount of potassium hydroxide required to neutralize the sulfonic acid contained in 1 g of the resin. The weight average molecular weight is determined by dissolving the resin to prepare a 0.02 mass % solution, passing it through a filter (GL Science, GL chromatography disk, water system 25 A, pore size 0.2 μm), and then using alliance (Nihon Waters) consisting of a particle size screening chromatography instrument and a refractive index detector under the following conditions. Column: pLgel mixed D (Agilent) × 2 pcs, connected in series Detector: alliance (Nihon Waters) Eluent: THF Flow rate: 1.0 ml/min Injection volume: 100 μl
＜顏料分散劑＞ （BYK-LPN23590） BYK-LPN23590（BYK-Chemie公司製造，固形物成分50%，AB嵌段結構，丙烯酸系）＜Pigment dispersant＞ (BYK-LPN23590) BYK-LPN23590 (manufactured by BYK-Chemie, solid content 50%, AB block structure, acrylic acid series)
＜鹼可溶性樹脂＞ （ZAH110） PHORET ZAH110（綜研化學公司製造，固形物成分35%）<Alkaline soluble resin> (ZAH110) PHORET ZAH110 (manufactured by Soken Chemical Co., Ltd., solid content 35%)
＜有機溶劑＞ （PGMEA） 丙二醇單甲醚乙酸酯 （PGME） 丙二醇單甲醚＜Organic solvent＞ (PGMEA) Propylene glycol monomethyl ether acetate (PGME) Propylene glycol monomethyl ether
＜光聚合性化合物＞ （DPEHA） 二新戊四醇六丙烯酸酯<Photopolymerizable compound> (DPEHA) Dipentaethrol hexaacrylate
＜光聚合起始劑＞ （Or907） 2-苄基-(二甲基胺基)-1-(4-啉基苯基)-1-丁酮（商品名：Omnirad907，IGM Resins B.V.公司製造）＜Photopolymerization initiator＞ （Or907） 2-Benzyl-(dimethylamino)-1-(4- (1-Butanone (Omnirad907, manufactured by IGM Resins BV)
＜微粒子化有機顏料＞ （微粒子化PR291-1） 於捏合機（商品名：KHD-2，井上製作所製造）之槽中投入10質量份的PR291、1質量份的PO71S、1質量份的樹脂1、200質量份的粒徑20 μm之氯化鈉、240質量份的二乙二醇，於50℃混練12小時進行鹽磨，獲得混練物。 繼而，將所獲得之混練物中之200質量份投入至2升溫水中，一面加熱至40℃一面攪拌1小時，形成漿料狀。 其後，反覆進行過濾、水洗，去除氯化鈉及二乙二醇後，於40℃進行乾燥，獲得微粒子化PR291-1。<Micronized organic pigment> (Micronized PR291-1) Into the tank of a kneader (trade name: KHD-2, manufactured by Inoue Seisakusho), 10 parts by mass of PR291, 1 part by mass of PO71S, 1 part by mass of resin 1, 200 parts by mass of sodium chloride with a particle size of 20 μm, and 240 parts by mass of diethylene glycol were added, kneaded at 50°C for 12 hours, and then salt-milled to obtain a kneaded product. Next, 200 parts by mass of the obtained kneaded product was added to 2 liters of warm water, and stirred for 1 hour while heating to 40°C to form a slurry. After that, filtration and water washing were repeated to remove sodium chloride and diethylene glycol, and then dried at 40°C to obtain micronized PR291-1.
（微粒子化PR291-2） 於上述微粒子化PR291-1之製造中，不使用PO71S，除此以外，同樣地獲得微粒子化PR291-2。(Micronized PR291-2) Micronized PR291-2 was obtained in the same manner as in the production of micronized PR291-1 except that PO71S was not used.
（微粒子化PR254-1） 於捏合機（商品名：KHD-2，井上製作所製造）之槽中投入10質量份的PR254、1質量份的PO71S、1質量份的樹脂1、200質量份的粒徑20 μm之氯化鈉、240質量份的二乙二醇，於50℃混練12小時進行鹽磨，獲得混練物。 繼而，將所獲得之混練物中之200質量份投入至2升溫水中，一面加熱至40℃一面攪拌1小時，形成漿料狀。 其後，反覆進行過濾、水洗，去除氯化鈉及二乙二醇後，於40℃進行乾燥，獲得微粒子化PR254-1。(Micronized PR254-1) Into the tank of a kneader (trade name: KHD-2, manufactured by Inoue Seisakusho), 10 parts by mass of PR254, 1 part by mass of PO71S, 1 part by mass of resin 1, 200 parts by mass of sodium chloride with a particle size of 20 μm, and 240 parts by mass of diethylene glycol were added, kneaded at 50°C for 12 hours, and then salt-milled to obtain a kneaded product. Next, 200 parts by mass of the obtained kneaded product was added to 2 liters of warm water, and stirred for 1 hour while heating to 40°C to form a slurry. Afterwards, filtering and washing were repeated to remove sodium chloride and diethylene glycol, and then dried at 40°C to obtain micronized PR254-1.
（微粒子化PR254-2） 於上述微粒子化PR254-1之製造中，使用樹脂2代替樹脂1，除此以外，同樣地獲得微粒子化PR254-2。(Micronized PR254-2) Micronized PR254-2 was obtained in the same manner as in the above micronized PR254-1 except that resin 2 was used instead of resin 1.
（微粒子化PR254-3） 於上述微粒子化PR254-1之製造中，使用樹脂3代替樹脂1，除此以外，同樣地獲得微粒子化PR254-3。(Micronized PR254-3) Micronized PR254-3 was obtained in the same manner as in the production of micronized PR254-1 except that resin 3 was used instead of resin 1.
（微粒子化PR254-4） 於上述微粒子化PR254-1之製造中，不使用樹脂1，除此以外，同樣地獲得微粒子化PR254-4。(Micronized PR254-4) Micronized PR254-4 was obtained in the same manner as in the production of micronized PR254-1, except that resin 1 was not used.
（微粒子化PR242） 於捏合機（商品名：KHD-2，井上製作所製造）之槽中投入10質量份的PR242、1質量份的PO71S、1質量份的樹脂1、200質量份的粒徑20 μm之氯化鈉、240質量份的二乙二醇，於50℃混練12小時進行鹽磨，獲得混練物。 繼而，將所獲得之混練物中之200質量份投入至2升溫水中，一面加熱至40℃一面攪拌1小時，形成漿料狀。 其後，反覆進行過濾、水洗，去除氯化鈉及二乙二醇後，於40℃進行乾燥，獲得微粒子化PR242。(Micronized PR242) Into the tank of a kneader (trade name: KHD-2, manufactured by Inoue Seisakusho), 10 parts by mass of PR242, 1 part by mass of PO71S, 1 part by mass of resin 1, 200 parts by mass of sodium chloride with a particle size of 20 μm, and 240 parts by mass of diethylene glycol were added, kneaded at 50°C for 12 hours, and then salt-milled to obtain a kneaded product. Next, 200 parts by mass of the obtained kneaded product was added to 2 liters of warm water, and stirred for 1 hour while heating to 40°C to form a slurry. After that, filtration and water washing were repeated to remove sodium chloride and diethylene glycol, and then dried at 40°C to obtain micronized PR242.
（微粒子化PR177） 於捏合機（商品名：KHD-2，井上製作所製造）之槽中投入10質量份的PR177、1質量份的PO71S、1質量份的樹脂1、200質量份的粒徑20 μm之氯化鈉、240質量份的二乙二醇，於50℃混練12小時進行鹽磨，獲得混練物。 繼而，將所獲得之混練物中之200質量份投入至2升溫水中，一面加熱至40℃一面攪拌1小時，形成漿料狀。 其後，反覆進行過濾、水洗，去除氯化鈉及二乙二醇後，於40℃進行乾燥，獲得微粒子化PR177。(Micronized PR177) Into the tank of a kneader (trade name: KHD-2, manufactured by Inoue Seisakusho), 10 parts by mass of PR177, 1 part by mass of PO71S, 1 part by mass of Resin 1, 200 parts by mass of sodium chloride with a particle size of 20 μm, and 240 parts by mass of diethylene glycol were added, kneaded at 50°C for 12 hours, and then salt-milled to obtain a kneaded product. Next, 200 parts by mass of the obtained kneaded product was added to 2 liters of warm water, and stirred for 1 hour while heating to 40°C to form a slurry. Afterwards, filtering and washing were repeated to remove sodium chloride and diethylene glycol, and then dried at 40°C to obtain micronized PR177.
＜濾色器用紅色著色組成物之製造＞ 以成為表1所記載之組成之方式混合各種材料，藉由Ready Mill（珠粒直徑：0.2 nm，填充率50%）混練融合60分鐘，獲得實施例及比較例之濾色器用紅色著色組成物。<Manufacturing of red coloring composition for color filter> The various materials were mixed in a manner to form the composition listed in Table 1, and kneaded and fused for 60 minutes using a Ready Mill (bead diameter: 0.2 nm, filling rate 50%) to obtain red coloring compositions for color filters of the embodiment and comparative example.
[表1]
＜濾色器用紅色著色阻劑組成物之製造＞ 以成為表2所記載之組成之方式使用高速攪拌機均勻地混合各種材料後，藉由孔徑3 μm之膜濾器進行過濾，獲得實施例及比較例之濾色器用紅色著色阻劑組成物。<Manufacturing of red coloring resist composition for color filter> After uniformly mixing various materials using a high-speed stirrer to obtain the composition shown in Table 2, filtering was performed through a membrane filter with a pore size of 3 μm to obtain the red coloring resist composition for color filter of the embodiment and the comparative example.
（評價用樣品之製作） 以分別成為相同膜厚之方式使用旋轉塗佈機將實施例及比較例之濾色器用紅色著色阻劑組成物塗佈於玻璃基板上。 其次，於100℃預烘烤3分鐘後，藉由高壓水銀燈進行曝光，進而於230℃後烘烤30分鐘，獲得各評價用樣品。(Preparation of samples for evaluation) The red coloring resist composition for the color filter of the embodiment and the comparative example was applied on a glass substrate using a rotary coater so as to have the same film thickness. Next, after pre-baking at 100°C for 3 minutes, it was exposed by a high-pressure mercury lamp and then post-baked at 230°C for 30 minutes to obtain each evaluation sample.
（光學特性評價） 使用分光光度計（島津製作所公司製造，UV-2500PC，C光源2°視野），測定上述各評價用樣品之色度x＝0.6400、y＝0.3290時之對比度及亮度Y。將其結果示於表2。 再者，對比度之測定中將空白組設為10000。(Evaluation of optical properties) Using a spectrophotometer (manufactured by Shimadzu Corporation, UV-2500PC, C light source 2° field of view), the contrast and brightness Y of the above-mentioned evaluation samples were measured when the chromaticity x = 0.6400 and y = 0.3290. The results are shown in Table 2. In addition, the blank group was set to 10000 in the measurement of contrast.
（昇華物評價） 藉由光學顯微鏡觀察上述各評價用樣品，其後，進而於260℃烘烤30分鐘後，再次藉由光學顯微鏡進行觀察，依據下述評價基準進行評價。將其結果示於表2。 ○：260℃烘烤後亦未確認到昇華物。 △：230℃烘烤後未確認到昇華物，但260℃烘烤後確認到些許昇華物。 ×：230℃烘烤後確認到昇華物。(Evaluation of sublimation) The above-mentioned samples for evaluation were observed under an optical microscope, and then further baked at 260°C for 30 minutes, and then observed again under an optical microscope, and evaluated according to the following evaluation criteria. The results are shown in Table 2. ○: No sublimation was observed even after baking at 260°C. △: No sublimation was observed after baking at 230°C, but some sublimation was observed after baking at 260°C. ×: Sublimation was observed after baking at 230°C.
[表2]
於使用實施例之濾色器用紅色著色組成物之實施例3、4之濾色器用紅色著色阻劑組成物中，確認到評價用樣品之對比度及亮度優異，起因於有機顏料之昇華物得到抑制。 又，根據實施例3與比較例7之比較，確認到藉由於鹽磨處理時含有吡咯并吡咯二酮化合物之磺化物，能夠進一步適當提高對比度。 又，於使用C.I.顏料紅242作為有機顏料之比較例8、使用C.I.顏料紅177作為有機顏料之比較例9中，亮度並不充分。 又，與實施例4相比較，使用不具有順丁烯二醯亞胺骨架之樹脂之比較例10、使用不具有磺酸基之樹脂之比較例11、於鹽磨處理時不使用樹脂之比較例12中產生昇華物，對比度及亮度亦不充分。 [產業上之可利用性]In the red coloring resist composition for color filters of Examples 3 and 4 using the red coloring composition for color filters of the embodiment, it was confirmed that the contrast and brightness of the evaluation samples were excellent, which was due to the suppression of the sublimation of the organic pigment. In addition, according to the comparison between Example 3 and Comparative Example 7, it was confirmed that the contrast can be further appropriately improved by containing the sulfonate of the diketopyrrolopyrrole compound during the salt milling treatment. In addition, in Comparative Example 8 using C.I. Pigment Red 242 as the organic pigment and Comparative Example 9 using C.I. Pigment Red 177 as the organic pigment, the brightness was not sufficient. Moreover, compared with Example 4, in Comparative Example 10 using a resin without a succinimidyl skeleton, Comparative Example 11 using a resin without a sulfonic acid group, and Comparative Example 12 using no resin during the salt milling treatment, sublimates were produced, and the contrast and brightness were also insufficient. [Industrial Applicability]
本發明之濾色器用紅色著色組成物之製造方法可提供一種起因於有機顏料之昇華物得到抑制，且能夠獲得對比度及亮度優異之濾色器的濾色器用紅色著色組成物，因此可適宜用作液晶顯示裝置或觸控面板等之濾色器中使用之濾色器用紅色著色阻劑組成物。The method for producing a red coloring composition for a color filter of the present invention can provide a red coloring composition for a color filter in which sublimation products caused by organic pigments are suppressed and a color filter with excellent contrast and brightness can be obtained. Therefore, the red coloring composition for a color filter can be suitably used as a red coloring resist composition for a color filter used in a color filter of a liquid crystal display device or a touch panel.
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