CN1504777A - 着色感光性树脂组合物 - Google Patents
着色感光性树脂组合物 Download PDFInfo
- Publication number
- CN1504777A CN1504777A CNA200310120454A CN200310120454A CN1504777A CN 1504777 A CN1504777 A CN 1504777A CN A200310120454 A CNA200310120454 A CN A200310120454A CN 200310120454 A CN200310120454 A CN 200310120454A CN 1504777 A CN1504777 A CN 1504777A
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- Prior art keywords
- acid
- methyl
- photosensitive composition
- pigment
- ester
- Prior art date
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- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 description 1
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- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- 125000005591 trimellitate group Chemical group 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
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- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
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Classifications
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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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/10—Amino derivatives of triarylmethanes
- C09B11/24—Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes
-
- 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
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
-
- 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
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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
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Abstract
本发明提供着色感光性树脂组合物,其特征在于在含有着色剂(A)、粘结剂聚合物(B)、光聚合性化合物(C)、光聚合引发剂(D)和溶剂(E)的着色感光性树脂组合物中,溶剂(E)含有丙二醇单甲基醚乙酸酯和4-羟基-4-甲基-2-戊酮。本发明还提供图案的形成方法,其特征在于将上述组合物涂布到基板上,除去挥发成分并形成着色层,通过光掩膜并将该着色层曝光,显像。
Description
技术领域
本发明涉及着色感光性树脂组合物。
背景技术
着色感光性树脂组合物,是含有着色剂的感光性树脂组合物,作为为形成构成彩色滤光片的着色图案的材料使用。此处,所谓彩色滤光片(カラ-フィルタ),是可用于将液晶显示装置的显示图像彩色化,或者是用于将通过固体摄像元件拍摄的图像彩色化中的光学元件。所谓着色图案,例如,是红、绿、蓝等颜色象素、黑色矩阵(ブラツクマトリツクス)等,有线状的、也有马赛克状的。
近年来,随着彩色滤光片生产量的增加,在其制造中使用的着色感光性树脂组合物的生产也同时增大。但是,如果要大量生产着色感光性树脂组合物,实际上直至用于彩色滤光片的制造的库存时间很长,此时着色感光性树脂组合物的着色剂成分发生沉降等,如果将其原样用于彩色滤光片的制造,存在所谓成品率降低的问题。因此,提出了通过将颜料用脂肪醇和脂肪胺处理来改善颜料的分散性,同时改善彩色滤光片形成材料的经时稳定性(保存稳定性)的方法(参照日本专利文献1),但是不能说其是经时稳定性良好的。
日本专利文献1
特开平9-178923号公报。
发明内容
本发明的目的在于提供经时稳定性良好的着色感光性树脂组合物。
本发明者们,为了发现可以解决上述问题的着色感光性树脂组合物,进行了反复深入的研究,结果发现,通过作为着色感光性树脂组合物的溶剂,使用含有丙二醇单甲基醚乙酸酯和4-羟基-4-甲基-2-戊酮的溶剂,可以改善着色感光性树脂组合物的经时稳定性,从而完成了本发明。
即,本发明提供了着色感光性树脂组合物,其特征在于在含有着色剂(A)、粘结剂聚合物(B)、光聚合性化合物(C)、光聚合引发剂(D)和溶剂(E)的感光性树脂组合物中,溶剂(E)含有丙二醇单甲基醚乙酸酯和4-羟基-4-甲基-2-戊酮。
另外,本发明提供图案的形成方法,其特征在于将上述组合物涂布在基板上,除去挥发性成分并形成着色层,通过光掩膜对该着色层进行曝光,并进行显像。
具体实施方式
本发明的着色感光性树脂组合物含有着色剂(A)、粘结剂聚合物(B)、光聚合性化合物(C)、光聚合引发剂(D)和溶剂(E),溶剂(E)含有丙二醇单甲基醚乙酸酯和4-羟基-4-甲基-2-戊酮。
本发明中使用的着色剂(A),优选为颜料,作为颜料,可以列举有机颜料,无机颜料。
作为颜料,具体地,可以列举颜料索引(The Society of Dyers and Colourists出版)中被分类在颜料(Pigment)中的化合物。具体地,可以列举例如C.I.颜料黄1,C.I.颜料黄3,C.I.颜料黄12,C.I.颜料黄13,C.I.颜料黄14,C.I.颜料黄15,C.I.颜料黄16,C.I.颜料黄17,C.I.颜料黄20,C.I.颜料黄24,C.I.颜料黄31,C.I.颜料黄53,C.I.颜料黄83,C.I.颜料黄86,C.I.颜料黄93,C.I.颜料黄94,C.I.颜料黄109,C.I.颜料黄110,C.I.颜料黄117,C.I.颜料黄125,C.I.颜料黄128,C.I.颜料黄137,C.I.颜料黄138,C.I.颜料黄139,C.I.颜料黄147,C.I.颜料黄148,C.I.颜料黄150,C.I.颜料黄153,C.I.颜料黄154,C.I.颜料黄166,C.I.颜料黄173,C.I.颜料黄194,C.I.颜料黄214等黄色颜料;
C.I.颜料橙13,C.I.颜料橙31,C.I.颜料橙36,C.I.颜料橙38,C.I.颜料橙40,C.I.颜料橙42,C.I.颜料橙43,C.I.颜料橙5 1,C.I.颜料橙55,C.I.颜料橙59,C.I.颜料橙61,C.I.颜料橙64,C.I.颜料橙65,C.I.颜料橙71,C.I.颜料橙73等橙色颜料;
C.I.颜料红9,C.I.颜料红97,C.I.颜料红105,C.I.颜料红122,C.I.颜料红123,C.I.颜料红144,C.I.颜料红149,C.I.颜料红166,C.I.颜料红168,C.I.颜料红176,C.I.颜料红177,C.I.颜料红180,C.I.颜料红192,C.I.颜料红209,C.I.颜料红215,C.I.颜料红216,C.I.颜料红224,C.I.颜料红242,C.I.颜料红254,C.I.颜料红255,C.I.颜料红264,C.I.颜料红265等红色颜料;
C.I.颜料蓝15,C.I.颜料蓝15:3,C.I.颜料蓝15:4,C.I.颜料蓝15:6,C.I.颜料蓝60等蓝色颜料;
C.I.颜料紫1,C.I.颜料紫19,C.I.颜料紫23,C.I.颜料紫29,C.I.颜料紫32,C.I.颜料紫36,C.I.颜料紫38等紫色颜料;
C.I.颜料绿7,C.I.颜料绿36等绿色颜料;
C.I.颜料棕23,C.I.颜料棕25等棕色颜料;
C.I.颜料黑1,C.I.颜料黑7等黑色颜料等,优选含有选自C.I.颜料黄138,C.I.颜料黄139,C.I.颜料黄150,C.I.颜料红177,C.I.颜料红209,C.I.颜料红254,C.I.颜料紫23,C.I.颜料蓝15∶6和C.I.颜料绿36中的至少一种颜料。
这些颜料,可以单独使用,也可以2种以上混合使用。
例如,要形成红色象素,优选含有C.I.颜料红209和C.I.颜料黄139;要形成绿色象素,优选含有C.I.颜料绿36以及选自C.I.颜料黄150和C.I.颜料黄138中的至少一种;要形成蓝色象素,优选含有C.I.颜料蓝15∶6。
其中,由于耐热性、发色性优异,优选使用有机颜料。
上述颜料中的有机颜料,根据需要,可以实施松香处理,使用导入酸性基团或碱性基团的颜料衍生物等的表面处理,采用高分子化合物等在颜料表面的接枝处理,采用硫酸微粒化法等微粒化处理,以及采用用于除去杂质的有机溶剂和水等的洗涤处理,离子性杂质通过离子交换法等除去处理等。
着色感光性树脂组合物的固体成分中的着色剂(A)的含量,优选为25质量%以上60质量%以下,更优选为27质量%以上55质量%以下,进一步优选30质量%以上50质量%以下。
着色剂(A)的含量如果在25质量%以上60质量%以下,作为彩色滤光片时的色浓度充分,而且由于组合物中可以以必须量含有粘结剂聚合物,可以形成机械强度充分的图案,因此是优选的。
此处,所谓着色感光性树脂组合物的固体成分,是指从着色感光性树脂组合物中除去溶剂(E)后残留的部分。
着色剂(A),优选为粒径均一的。着色剂(A)是颜料的情况下,通过含有颜料分散剂并进行分散处理,可以得到颜料均匀地在溶液中分散的状态的颜料分散液。
作为上述的颜料分散剂,可以列举例如阳离子系,阴离子系,非离子系,两性,聚酯系,聚胺系等表面活性剂等,可以单独也可以组合2种以上使用。
颜料分散剂的使用量,每1质量份着色剂(A),优选为1质量份以下,更优选为0.05质量份以上0.5质量份以下。上述颜料分散剂的使用量如果为每1质量份着色剂1质量份以下,由于有可得到均匀分散状态的颜料的倾向,因此是优选的。
作为本发明中使用的粘结剂聚合物(B),可以列举例如含有羧基的单体和与该单体可共聚的其他单体的共聚物等的丙烯酸系共聚物等。
作为含有羧基的单体,可以列举例如在不饱和单羧酸、不饱和二羧酸、不饱和三羧酸等不饱和多元羧酸等的分子中具有至少一个羧基的不饱和羧酸。
此处,作为不饱和单羧酸,可以列举例如丙烯酸,甲基丙烯酸,巴豆酸,α-氯丙烯酸,肉桂酸等。作为不饱和二羧酸,可以列举例如马来酸,富马酸,衣康酸,柠康酸,中康酸等。
不饱和多元羧酸,可以是马来酸酐,衣康酸酐,柠康酸酐等酸酐。另外,不饱和多元羧酸,可以是其单(2-甲基丙烯酰氧基烷基)酯,例如琥珀酸单(2-丙烯酰氧基乙基)酯,琥珀酸单(2-甲基丙烯酰氧基乙基)酯,邻苯二甲酸单(2-丙烯酰氧基乙基)酯,邻苯二甲酸单(2-甲基丙烯酰氧基乙基)酯等。不饱和多元羧酸,可以是其两末端的二羧基聚合物的单(甲基)丙烯酸酯,可以列举例如ω-羧基聚己内酯单丙烯酸酯,ω-羧基聚己内酯单甲基丙烯酸酯等。这些含有羧基的单体,可以单独也可以2种以上混合使用。
作为上述的与含有羧基的单体可共聚的其他单体,可以列举例如苯乙烯,α-甲基苯乙烯,邻-乙烯基甲苯,间-乙烯基甲苯,对-乙烯基甲苯,对-氯苯乙烯,邻-甲氧基苯乙烯,间-甲氧基苯乙烯,对-甲氧基苯乙烯,邻-乙烯基苄基甲醚,间-乙烯基苄基甲醚,对-乙烯基苄基甲醚,邻-乙烯基苄基缩水甘油基醚,间-乙烯基苄基缩水甘油基醚,对-乙烯基苄基缩水甘油基醚,茚等芳香族乙烯基化合物;丙烯酸甲酯,甲基丙烯酸甲酯,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,丙烯酸异丙酯,甲基丙烯酸异丙酯,丙烯酸正丁酯,甲基丙烯酸正丁酯,丙烯酸异丁酯,甲基丙烯酸异丁酯,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2-羟基乙酯,甲基丙烯酸2-羟基乙酯,丙烯酸2-羟基丙酯,甲基丙烯酸2-羟基丙酯,丙烯酸3-羟基丙酯,甲基丙烯酸3-羟基丙酯,丙烯酸2-羟基丁酯,甲基丙烯酸2-羟基丁酯,丙烯酸3-羟基丁酯,甲基丙烯酸3-羟基丁酯,丙烯酸4-羟基丁酯,甲基丙烯酸4-羟基丁酯,丙烯酸烯丙酯,甲基丙烯酸烯丙酯,丙烯酸苄基酯,甲基丙烯酸苄基酯,丙烯酸环己酯,甲基丙烯酸环己酯,丙烯酸苯酯,甲基丙烯酸苯酯,丙烯酸2-甲氧基乙酯,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,丙烯酸甲氧基二甘醇酯,甲基丙烯酸甲氧基二甘醇酯,丙烯酸甲氧基三甘醇酯,甲基丙烯酸甲氧基三甘醇酯,丙烯酸甲氧基丙二醇酯,甲基丙烯酸甲氧基丙二醇酯,丙烯酸甲氧基二丙二醇酯,甲基丙烯酸甲氧基二丙二醇酯,丙烯酸异冰片基酯,甲基丙烯酸异冰片基酯,丙烯酸二戊二烯酯,甲基丙烯酸二戊二烯酯,丙烯酸2-羟基-3-苯氧基丙酯,甲基丙烯酸2-羟基-3-苯氧基丙酯,甘油单丙烯酸酯,甘油单甲基丙烯酸酯等不饱和羧酸酯类;
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,甲基丙烯酸3-二甲基氨基丙酯等不饱和羧酸氨基烷基酯类;
丙烯酸缩水甘油酯,甲基丙烯酸缩水甘油酯等不饱和羧酸缩水甘油酯类;
醋酸乙烯酯,丙酸乙烯酯,丁酸乙烯酯,苯甲酸乙烯酯等羧酸乙烯酯类;
乙烯基甲基醚,乙烯基乙基醚,烯丙基缩水甘油基醚等不饱和醚类;
丙烯腈,甲基丙烯腈,α-氯丙烯腈,氰化乙烯叉等氰化乙烯基化合物;
丙烯酰胺,甲基丙烯酰胺,α-氯丙烯酰胺,N-2-羟基乙基丙烯酰胺,N-2-羟基乙基甲基丙烯酰胺等不饱和酰胺类;
马来酰胺,N-苯基马来酰胺,N-环己基马来酰胺等不饱和酰胺类;
1,3-丁二烯,异戊二烯,氯丁二烯等脂肪族共轭二烯类;
在聚苯乙烯,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,聚硅氧烷的聚合物分子链末端具有单丙烯酰基或单甲基丙烯酰基的大分子单体类等。
这些单体,可以单独也可以2种以上混合使用。
上述共聚物种的含有羧基的单体单元的含量,优选为10~50质量%,更优选为15~40质量%,进一步优选为25~40质量%。上述含有羧基的单体单元的含量,如果为10~50质量%,对于显像液溶解性良好,显像时具有正确地形成图像的倾向,因此是优选的。
作为上述丙烯酸系共聚物,可以列举例如(甲基)丙烯酸/(甲基)丙烯酸甲酯共聚物,(甲基)丙烯酸/(甲基)丙烯酸苄基酯共聚物,(甲基)丙烯酸/(甲基)丙烯酸2-羟基乙酯/(甲基)丙烯酸苄基酯共聚物,(甲基)丙烯酸/(甲基)丙烯酸甲酯/聚苯乙烯大分子单体共聚物,(甲基)丙烯酸/(甲基)丙烯酸甲酯/聚(甲基)丙烯酸甲酯大分子单体共聚物,(甲基)丙烯酸/(甲基)丙烯酸苄基酯/聚苯乙烯大分子单体共聚物,(甲基)丙烯酸/(甲基)丙烯酸苄基酯/聚(甲基)丙烯酸甲酯大分子单体共聚物,(甲基)丙烯酸/(甲基)丙烯酸2-羟基乙酯/(甲基)丙烯酸苄基酯/聚苯乙烯大分子单体共聚物,(甲基)丙烯酸/(甲基)丙烯酸2-羟基乙酯/(甲基)丙烯酸苄基酯/聚(甲基)丙烯酸甲酯大分子单体共聚物,(甲基)丙烯酸/苯乙烯/(甲基)丙烯酸苄基酯/N-苯基马来酰胺共聚物,(甲基)丙烯酸/琥珀酸单(2-丙烯酰氧基乙基)酯/苯乙烯/(甲基)丙烯酸苄基酯/N-苯基马来酰胺共聚物,(甲基)丙烯酸/琥珀酸单(2-丙烯酰氧基乙基)酯/苯乙烯/(甲基)丙烯酸烯丙酯/N-苯基马来酰胺共聚物,(甲基)丙烯酸/(甲基)丙烯酸苄基酯/N-苯基马来酰胺/苯乙烯/甘油单(甲基)丙烯酸酯共聚物等。另外,所谓(甲基)丙烯酸酯,表示丙烯酸酯或者甲基丙烯酸酯。
其中,优选使用(甲基)丙烯酸/(甲基)丙烯酸苄基酯共聚物,(甲基)丙烯酸/(甲基)丙烯酸苄基酯/苯乙烯共聚物,(甲基)丙烯酸/(甲基)丙烯酸甲酯共聚物,(甲基)丙烯酸/(甲基)丙烯酸甲酯/苯乙烯共聚物。
上述丙烯酸系共聚物,其聚苯乙烯换算的重量平均分子量为3,000~400,000、更优选为5,000~100,000、更进一步优选为10,000~40,000。分子量如果为3,000~400,000,由于涂膜硬度提高,残膜率也高,未曝光部分对显像液的溶解性良好,存在清晰度提高的倾向,因此是优选的。
另外,上述丙烯酸系共聚物的酸值优选为30~250,更优选为60~180,进一步优选为80~160。上述酸值,如果为30~250,对显像液的溶解性提高且未曝光部分容易溶解,另外高感光度化并且显像时曝光部分的图案残留,存在残膜率提高的倾向,因此是优选的。此处,酸值是以中和1g丙烯酸聚合物所必须的氢氧化钾的量(mg)形式测定的值,通常可以通过用氢氧化钾水溶液滴定求出。
着色感光性树脂组合物的固体成分中粘结剂聚合物(B)的含量,优选为5质量%以上90质量%以下,更优选10质量%以上80质量%以下,更进一步优选20质量%以上70质量%以下。含量如果在5质量%以上90质量%以下,图案中不容易掺入凹陷,存在粘合性良好的倾向,另外存在清晰度和残膜率提高的倾向,因此是优选的。
本发明中使用的光聚合性化合物(C),是由通过照射光从光聚合引发剂(D)产生的活性自由基、酸等聚合的化合物,可以列举例如具有聚合性碳-碳不饱和键的化合物等。
上述光聚合性化合物(C),优选为具有3个官能基以上的多官能的光聚合性化合物。作为3个官能基以上的多官能的光聚合性化合物,可以列举例如季戊四醇四丙烯酸酯,季戊四醇四甲基丙烯酸酯,二季戊四醇五丙烯酸酯,二季戊四醇五甲基丙烯酸酯,二季戊四醇六丙烯酸酯,二季戊四醇六甲基丙烯酸酯等。上述光聚合性化合物(C),可以单独也可以组合2种以上使用。
着色感光性树脂组合物的固体成分中的光聚合性化合物(C)的含量,优选为5质量%以上90质量%以下,更优选为10质量%以上80质量%以下,,更进一步优选20质量%以上70质量%以下。上述光聚合性化合物(C)的含量,如果在5质量%以上90质量%以下,充分地发生固化且残膜率提高,图案中难以掺入凹陷,存在粘合性良好的倾向,因此是优选的。
本发明中使用的光聚合引发剂(D),优选含有至少一种苯乙酮系化合物。
作为苯乙酮系化合物,可以列举例如二乙氧基苯乙酮,2-甲基-2-吗啉代-1-(4-甲基硫代苯基)丙烷-1-酮,2-羟基-2-甲基-1-苯基丙烷-1-酮,苄基二甲基缩酮,2-羟基-2-甲基-1-[4-(2-羟基乙氧基)苯基]丙烷-1-酮,1-羟基环己基苯基酮,2-羟基-2-甲基-1-[4-(1-甲基乙烯基)苯基]丙烷-1-酮等低聚物等,优选2-甲基-2-吗啉代-1-(4-甲基硫代苯基)丙烷-1-酮等。另外,可以将多个苯乙酮系和其他的光聚合引发剂组合使用。作为苯乙酮系以外的光聚合引发剂,可以举出通过照射光产生活性自由基的活性自由基产生剂,酸产生剂等。
作为活性自由基引发剂,可以列举例如苯偶姻系化合物,二苯甲酮系化合物,噻吨酮系化合物,三嗪系化合物等。
作为苯偶姻系化合物,可以列举例如苯偶姻,苯偶姻甲基醚,苯偶姻乙基醚,苯偶姻异丙基醚,苯偶姻异丁基醚等。
作为二苯甲酮系化合物,可以列举例如二苯甲酮,邻-苯甲酰基苯甲酸甲酯,4-苯基二苯甲酮,4-苯甲酰基-4’-甲基二苯基亚硫酸盐,3,3’,4,4’-四(叔丁基过氧羰基)二苯甲酮,2,4,6-三甲基二苯甲酮等。
作为噻吨酮系化合物,可以列举例如2-异丙基噻吨酮,4-异丙基噻吨酮,2,4-二乙基噻吨酮,2,4-二氯噻吨酮,1-氯-4-丙氧基噻吨酮等。
作为三嗪系化合物,可以列举例如,2,4-双(三氯甲基)-6-(4-甲氧基苯基)-1,3,5-三嗪,2,4-双(三氯甲基)-6-(4-甲氧基萘基)-1,3,5-三嗪,2,4-双(三氯甲基)-6-(4-甲氧基苯乙烯基)-1,3,5-三嗪,2,4-双(三氯甲基)-6-[2-(5-甲基呋喃-2-基)乙烯基]-1,3,5-三嗪,2,4-双(三氯甲基)-6-[2-(呋喃-2-基)乙烯基]-1,3,5-三嗪,2,4-双((三氯甲基)-6-[2-(4-二乙基氨基-2-甲基苯基)乙烯基]-1,3,5-三嗪,2,4-双(三氯甲基)-6-[2-(3,4-二甲氧基苯基)乙烯基]-1,3,5-三嗪等。
作为活性自由基产生剂,可以使用例如2,4,6-三甲基苯甲酰基二苯基氧化膦,2,2’-双(邻-氯苯基)-4,4’,5,5’-四苯基-1,2’-二咪唑,10-丁基-2-氯吖啶酮,2-乙基蒽醌,苄基,9,10-菲醌,莰醌,苯基乙醛酸甲酯,二茂钛(チタノセン)化合物等。
作为酸产生剂,可以列举例如4-羟基苯基二甲基锍对甲苯磺酸酯,4-羟基苯基二甲基锍六氟锑酸盐,4-乙酰氧基苯基二甲基锍对甲苯磺酸酯,4-乙酰氧基苯基·甲基·苄基锍六氟锑酸盐,三苯基锍对甲苯磺酸酯,三苯基锍六氟锑酸盐,二苯基碘鎓(ョ-ドニゥム)对甲苯磺酸酯,二苯基碘鎓六氟锑酸盐等鎓盐类,或硝基苄基甲苯磺酸盐(トシレ-ト)类,苯偶姻甲苯磺酸盐类等。
另外,作为活性自由基产生剂的上述化合物中,也可以是同时产生活性自由基和酸的化合物,例如,三嗪系光聚合引发剂,也可以作为酸产生剂使用。
光聚合物引发剂(D)的含量,相对于粘结剂聚合物(B)和光聚合性化合物(C)的总量100质量份,优选为0.1质量份以上20质量份以下,更优选为1质量份以上15质量份以下。光聚合引发剂的含量,如果为0.1质量份以上20质量份以下,高感光化且曝光时间缩短生产率提高,另一方面,存在感光度过高清晰度不变差的倾向,因此是优选的。
本发明的着色感光性树脂组合物中,可以进一步含有光聚合引发助剂(G)。光聚合引发助剂(G),通常是可以与光聚合引发剂(D)联合使用并为了促进通过光聚合引发剂开始聚合的光聚合性化合物的聚合而使用的化合物。
作为光聚合引发剂助剂(G),可以列举胺系化合物,烷氧基蒽系化合物,噻吨酮系化合物等。
作为胺类化合物,可以列举例如三乙醇胺,甲基二乙醇胺,三异丙醇胺,4-二甲基氨基苯甲酸甲酯,4-二甲基氨基苯甲酸乙酯,4-二甲基氨基苯甲酸异戊酯,苯甲酸2-二甲基氨基乙酯,4-二甲基氨基苯甲酸2-乙基己酯,N,N-二甲基对甲苯胺,4,4’-双(二甲基氨基)二甲苯酮(俗称米斯勒氏酮),4,4’-双(二乙基氨基)二苯甲酮,4,4’-双(乙基甲基氨基)二苯甲酮等,其中,优选4,4’-双(二乙基氨基)二苯甲酮。
作为烷氧基蒽系化合物,可以列举例如9,10-二甲氧基蒽,2-乙基-9,10-二甲氧基蒽,9,10-二乙氧基蒽,2-乙基-9,10-二乙氧基蒽等。
作为噻吨酮系化合物,可以列举例如2-异丙基噻吨酮,4-异丙基噻吨酮,2,4-二乙基噻吨酮,2,4-二氯噻吨酮,1-氯-4-丙氧基噻吨酮等。
光聚合引发助剂(G),可以单独或组合2种以上使用。另外,作为光聚合引发助剂(G),可以使用市售的,作为市售的光聚合引发助剂(G),可以列举例如商品名为“EAB-F”(保土谷化学工业(株)制)等。
作为本发明的着色感光性树脂组合物中的光聚合引发剂(D)和光聚合引发助剂(G)的组合,可以列举例如二乙氧基苯乙酮/4,4’-双(二乙基氨基)二甲苯酮,2-甲基-2-吗啉代-1-(4-甲基硫代苯基)丙烷-1-酮/4,4’-双(二乙基氨基)二苯甲酮,2-羟基-2-甲基-1-苯基丙烷-1-酮/4,4’-双(二乙基氨基)二苯甲酮,苄基二甲基缩酮/4,4’-双(二乙基氨基)二苯甲酮,2-羟基-2-甲基-1-[4-(2-羟基乙氧基)苯基]丙烷-1-酮/4,4’-双(二乙基氨基)二苯甲酮,1-羟基环己基苯基酮/4,4’-双(二乙基氨基)二苯甲酮,2-羟基-2-甲基-1-[4-(1-甲基乙烯基)苯基]丙烷-1-酮的低聚物/4,4’-双(二乙基氨基)二苯甲酮,2-苄基-2-二甲基氨基-1-(4-吗啉代苯基)丁烷-1-酮/4,4’-双(二乙基氨基)二苯甲酮等,优选地可列举2-甲基-2-吗啉代-1-(4-甲基硫代苯基)丙烷-1-酮/4,4’-双(二乙基氨基)二苯甲酮等。
使用这些光聚合引发助剂(G)时,其使用量,每1摩尔光聚合引发剂(D),通常为10摩尔以下,优选为0.01摩尔以上5摩尔以下。
作为本发明中使用的溶剂(E),可以列举含有丙二醇单甲基醚乙酸酯和4-羟基-4-甲基-2-戊酮的溶剂。溶剂(E)中,可以含有除上述2种以外的其他溶剂。作为其他溶剂,可以列举例如上述以外的醚类,芳香烃类,上述酮以外的酮类,醇类,酯类,酰胺类,N-甲基吡咯烷酮,二甲基亚砜等。
作为醚类,可以列举例如四氢呋喃,四氢吡喃,1,4-二噁烷,乙二醇单甲基醚,乙二醇单乙基醚,乙二醇单丙基醚,乙二醇单丁基醚,二乙二醇单甲基醚,二乙二醇单乙基醚,二乙二醇单丁基醚,二乙二醇二甲基醚,二乙二醇二乙基醚,二乙二醇二丙基醚,二乙二醇二丁基醚,丙二醇单乙基醚乙酸酯,丙二醇单丙基醚乙酸酯,甲基溶纤剂乙酸酯,乙基溶纤剂乙酸酯,乙基卡必醇乙酸酯,丁基卡必醇乙酸酯,丙二醇甲基醚乙酸酯,甲氧基丁基乙酸酯,甲氧基戊基乙酸酯,茴香醚,苯乙醚,甲基茴香醚等。
作为芳香族烃类,可以列举苯,甲苯,二甲苯,均三甲苯等。
作为酮类,可以列举例如丙酮,2-丁酮,2-庚酮,3-庚酮,4-庚酮,4-甲基-2-庚酮,环庚酮,环己酮等。
作为醇类,可以列举例如甲醇,乙醇,丙醇,丁醇,己醇,环己醇,乙二醇,甘油等。
作为酯类,可以列举例如乙酸乙酯,乙酸-正丁酯,乙酸异丁酯,甲酸戊酯,乙酸异戊酯,乙酸异丁酯,丙酸丁酯,丁酸异丙酯,丁酸乙酯,丁酸丁酯,烷基酯类,乳酸甲酯,乳酸乙酯,羟乙酸甲酯,羟乙酸乙酯,羟乙酸丁酯,甲氧基乙酸甲酯,甲氧基乙酸乙酯,甲氧基乙酸丁酯,乙氧基乙酸甲酯,乙氧基乙酸乙酯,3-羟基丙酸甲酯,3-氧基丙酸乙酯,3-甲氧基丙酸甲酯,3-甲氧基丙酸乙酯,3-乙氧基丙酸甲酯,3-乙氧基丙酸乙酯,2-羟基丙酸甲酯,2-羟基丙酸乙酯,2-羟基丙酸丙酯,2-甲氧基丙酸甲酯,2-甲氧基丙酸乙酯,2-甲氧基丙酸丙酯,2-乙氧基丙酸甲酯,2-乙氧基丙酸乙酯,2-羟基-2-甲基丙酸甲酯,2-羟基-2-甲基丙酸乙酯,2-甲氧基-2-甲基丙酸甲酯,2-乙氧基-2-甲基丙酸乙酯,丙酮酸甲酯,丙酮酸乙酯,丙酮酸丙酯,乙酰乙酸甲酯,乙酰乙酸乙酯,2-氧代丁酸甲酯,2-氧代丁酸乙酯,3-甲氧基丁基乙酸酯,3-甲基-3-甲氧基丁基乙酸酯,γ-丁内酯等。
作为酰胺类,可以列举例如N,N-二甲基甲酰胺,N,N-二甲基乙酰胺等。
其中,优选联合使用3-乙氧基丙酸乙酯。
上述的溶剂,可以单独也可以组合2种以上使用。
着色感光性树脂组合物(总量)中的溶剂(E)的含量,优选为70质量%以上95质量%以下,更优选75质量%以上90质量%以下。溶剂的含量如果在70质量%以上95质量%以下,涂布时的平滑性良好,另外,由于形成彩色滤光片时色浓度不会不足,存在显示特性良好的倾向,因此是优选的。
溶剂(E)中的4-羟基-4-甲基-2-戊酮的含量,优选为3质量%以上40质量%以下,更优选为5质量以上30质量%以下,更进一步优选8质量%以上20质量%以下。溶剂(E),优选基本上由丙二醇单甲基醚乙酸酯和4-羟基-4-甲基-2-戊酮构成。
本发明的着色感光性树脂组合物中,还可以含有表面活性剂(F)。作为表面活性剂(F),可以列举选自硅酮系表面活性剂,氟系表面活性剂和具有氟原子的硅酮系表面活性剂中的至少一种。
作为硅酮系表面活性剂,可以列举例如具有硅氧烷键的表面活性剂等,具体地,可以列举例如ト-レ硅酮DC3PA,同SH7PA,同DC11PA,同SH21PA,同SH28PA,同29SHPA,同SH30PA,聚醚改性聚硅油SH8400(商品名:ト-レ硅酮(株)制),KP321,KP322,KP323,KP324,KP326,KP340,KP341(信越硅酮制),TSF400,TSF401,TSF410,TSF4300,TSF4440,TSF4445,TSF-4446,TSF4452,TSF4460(ジ-ィ-东芝硅酮(株)制)等。
作为氟系表面活性剂,可以列举具有氟碳链的表面活性剂等。具体地,可以列举フロリナ-ト(注册商标)FC430,同FC431(住友スリ-ェム(株)制),メガフアツク(注册商标)F142D,同F171,同F172,同F173,同F177,同F183,同R30(大日本油墨化学工业(株)制),ェフトツプ(注册商标)EF301,同EF303,同EF351,同EF352(新秋田化成(株)制),サ-フロン(注册商标)S381,同S382,同SC101,同SC105(旭硝子(株)制),E5844(株)ダィキンフアィンケミカル研究所制),BM-1000,BM-1100(商品名均为:BM Chemie社制)等。
作为具有氟原子的硅酮系表面活性剂,可以列举具有硅氧烷键和氟碳链的表面活性剂等。具体地,可以列举例如メカフアツク(注册商标)R08,同BL20,同F475,同F477,同F443(大日本油墨化学工业(株)制)等。
这些表面活性剂,可以单独也可以组合2种以上使用。
表面活性剂(F)的含量,相对于100质量份着色感光性树脂组合物((A)~(E)的总量)优选为0.0005质量份以上0.6质量份以下,更优选0.001质量份以上0.5质量份。表面活性剂(F)的含量如果在0.0005质量份以上0.6质量份以下,由于存在平滑性良好的倾向,因此是优选的。
本发明的着色感光性树脂组合物中,还可以含有填充剂,粘结剂聚合物以外的高分子化合物,粘着促进剂,抗氧化剂,紫外线吸收剂,防凝结剂,有机酸,有机氨基化合物,固化剂等添加剂。
作为填充剂,可以列举例如玻璃,氧化铝等微粒。
作为粘结剂聚合物以外的高分子化合物,可以列举例如聚乙烯醇,聚丙烯酸,聚乙二醇单烷基醚,聚丙烯酸氯烷基酯等。
作为粘着促进剂,可以列举例如乙烯基三甲氧基硅烷,乙烯基三乙氧基硅烷,乙烯基三(2-甲氧基乙氧基)硅烷,N-(2-氨基乙基)-3-氨基丙基甲基二甲氧基硅烷,N-(2-氨基乙基)-3-氨基丙基三甲氧基硅烷,3-氨基丙基三乙氧基硅烷,3-环氧丙氧基丙基三甲氧基硅烷,3-环氧丙氧基甲基二甲氧基硅烷,2-(3,4-乙氧基环己基)乙基三甲氧基硅烷,3-氯丙基甲基二甲氧基硅烷,3-氯丙基三甲氧基硅烷,3-甲基丙烯基氧基丙基三甲氧基硅烷,3-巯基丙基三甲氧基硅烷等。
作为抗氧化剂,可以列举例如4,4’-硫代二(6-叔丁基-3-甲基苯酚),2,6-二-叔丁基-4-甲基苯酚等。
作为紫外线吸收剂,可以列举例如2-(2-羟基-3-叔丁基-5-甲基苯基)-5-氯苯并三唑等苯并三唑系;
2-羟基-4-辛基氧二苯甲酮等二苯甲酮系;
2,4-二-叔丁基苯基-3,5-二-叔丁基-4-羟基苯甲酸酯等苯甲酸酯系;
2-(4,6-二苯基-1,3,5-三嗪-2-基)-5-己基氧代苯酚等三嗪系。
作为防凝结剂,可以列举例如聚丙烯酸钠等。作为有机酸,可以列举例如甲酸,乙酸,丙酸,丁酸,戊酸,新戊酸,己酸,二乙基乙酸,庚酸,辛酸等脂肪族单羧酸类;
草酸,丙二酸,琥珀酸,戊二酸,己二酸,庚二酸,辛二酸,壬二酸,癸二酸,十三烷二酸,甲基丙二酸,乙基丙二酸,二甲基丙二酸,甲基琥珀酸,四甲基琥珀酸,环己二羧酸,衣康酸,甲基马来酸,马来酸,富马酸,中康酸等脂肪族二羧酸类;
丙三酸,乌头酸,樟脑三酸等脂肪族三羧酸类;
苯甲酸,甲苯甲酸,枯茗酸,二甲基苯甲酸,3,5-二甲基苯甲酸等芳香族单羧酸类;
邻苯二甲酸,间苯二甲酸,对苯二甲酸等芳香族二羧酸类;
偏苯三酸,均苯三酸,偏苯四酸,均苯四酸等芳香族多羧酸类等。
作为有机氨基化合物,可以列举例如正丙胺,异丙胺,正丁胺,异丁胺,仲丁胺,叔丁胺,正戊胺,正己胺,正庚胺,正辛胺,正壬胺,正癸胺,正十一胺,正十二胺等单烷基胺类;
环己胺,2-甲基环己胺,3-甲基环己胺,4-甲基环己胺等单环烷基胺类;
甲基乙基胺,二乙基胺,甲基正丙基胺,乙基正丙基胺,二正丙基胺,二异丙基胺,二正丁基胺,二异丁基胺,二仲丁基胺,二叔丁基胺,二正戊基胺,二正己基胺等二烷基胺类;
甲基环己胺,乙基环己胺等单烷基单环烷基胺类;
二环己基胺等二环烷基胺类;
二甲基乙基胺,甲基二乙基胺,三乙胺,二甲基正丙胺,二乙基正丙胺,甲基二正丙胺,乙基二正丙胺,三正丙胺,三异丙胺,三正丁胺,三异丁胺,三仲丁胺,三叔丁胺,三正戊胺,三正己胺等三烷基胺类;
二甲基环己胺,二乙基环己胺等二烷基单环烷基胺类;
甲基二环己胺,乙基二环己胺,三环己基胺等单烷基二环烷基胺类;
二氨基乙醇,3-氨基-1-丙醇,1-氨基-2-丙醇,4-氨基-1-丁醇,5-氨基-1-戊醇,6-氨基-1-己醇等单链烷醇胺类;
4-氨基-1-环己醇等单环烷醇胺类;
二乙醇胺,二正丙醇胺,二异丙醇胺,二正丁醇胺,二异丁醇胺,二正戊醇胺,二己醇胺等二链烷醇胺类;
二(4-环己醇)胺等二环烷醇胺类;
三乙醇胺,三正丙醇胺,三异丙醇胺,三正丁醇胺,三异丁醇胺,三正戊醇胺,三正己醇胺等三链烷醇胺类;
三(4-环己醇)胺等三环烷醇胺类;
3-氨基-1,2-丙二醇,2-氨基-1,3-丙二醇,4-氨基-1,2-丁二醇,4-氨基-1,3-丁二醇,3-二甲基氨基-1,2-丙二醇,3-二乙基氨基-1,2-丙二醇,2-二甲基氨基-1,3-丙二醇,2-二乙基氨基-1,3-丙二醇等氨基链烷二醇类;
4-氨基-1,2-环己二醇,4-氨基-1,3-环己二醇等氨基环烷二醇类;
1-氨基环戊酮甲醇,4-氨基环戊酮甲醇等含有氨基的环烷酮甲醇类;
1-氨基环己酮甲醇,4-氨基环己酮甲醇,4-二甲基氨基环戊酮甲醇,4-二乙基氨基环戊酮甲醇,4-二甲基氨基环己酮甲醇,4-二乙基氨基环己酮甲醇等含有氨基的环烷酮甲醇类;
β-丙氨酸,2-氨基丁酸,3-氨基丁酸,4-氨基丁酸,2-氨基异丁酸,3-氨基异丁酸,2-氨基戊酸,5-氨基戊酸,6-氨基己酸,1-氨基环丙酸,1-氨基环己羧酸,4-氨基环己羧酸等氨基羧酸类;
苯胺,邻-甲基苯胺。间-甲基苯胺,对-甲基苯胺,对-乙基苯胺,对-正丙基苯胺,对异丙基苯胺,对-正丁基苯胺,对-叔丁基苯胺,1-萘基胺,2-萘基胺,N,N-二甲基苯胺,N,N-二乙基苯胺,对-甲基-N,N-二甲基苯胺等芳香族胺类;
邻-氨基苄基醇,间-氨基苄基醇,对-氨基苄基醇,对-二甲基氨基苄基醇,对-二乙基氨基苄基醇等氨基苄基烷醇类;
邻-氨基苯酚,间-氨基苯酚,对-氨基苯酚,对-二甲基氨基苯酚,对-二乙基氨基苯酚等氨基苯酚类等;
间-氨基苯甲酸,对-氨基苯甲酸,对-二甲基氨基苯甲酸,对-二乙基氨基苯甲酸等氨基苯甲酸类。
作为固化剂,可以列举例如,通过加热与粘结剂聚合物中的羧基反应并可以使粘结剂聚合物交联的化合物,可以单独聚合并使着色图案固化的化合物等。作为上述化合物,可以列举例如环氧化合物,氧杂环丁烷化合物等,优选使用氧杂环丁烷化合物。
此处,作为环氧化合物,可以列举例如双酚A系环氧树脂,氢化双酚A系环氧树脂,双酚F系环氧树脂,氢化双酚F系环氧树脂,酚醛清漆型环氧树脂,其它芳香族系环氧树脂,脂环族系环氧树脂,杂环式环氧树脂,缩水甘油酯系树脂,缩水甘油胺系树脂,环氧化油等环氧树脂,和这些环氧树脂的溴化衍生物,环氧树脂和其溴化衍生物以外的脂肪族,脂环族或芳香族环氧化合物,丁二烯(共)聚合物的环氧化物,异戊二烯的(共)聚物的环氧化物,缩水甘油基(甲基)丙烯酸酯的(共)聚合物,三缩水甘油基异氰尿酸酯等。
作为氧杂环丁烷化合物,可以列举例如碳酸酯二氧杂环丁烷,亚二甲苯基二氧杂环丁烷,己二酸酯二氧杂环丁烷,对苯二甲酸酯二氧杂环丁烷,环己烷二羧酸二氧杂环丁烷等。
本发明的着色感光性树脂组合物,作为固化剂含有环氧化合物、氧杂环丁烷化合物等的情况下,可以含有可以使环氧化合物的环氧基,氧杂环丁烷化合物氧杂环丁烷骨架开环聚合的化合物。作为该化合物,可以列举例如多元羧酸类,多元羧酸酐类等。
作为多元羧酸类,可以列举例如邻苯二甲酸,3,4-二甲基苯二甲酸,间苯二甲酸,对苯二甲酸,均苯四甲酸,偏苯三甲酸,1,4,5,8-萘四酸,3,3’,4,4’-二苯甲酮四羧酸等芳香族多元羧酸类;
琥珀酸,戊二酸,己二酸,1,2,3,4-丁基四羧酸,马来酸,富马酸,衣康酸等脂肪族多元羧酸类;
六氢邻苯二甲酸,3,4-二甲基四氢邻苯二甲酸,六氢间苯二甲酸,六氢对苯二甲酸,1,2,4-环戊烷三羧酸,1,2,4-环己三羧酸,环戊四羧酸,1,2,4,5-环己四羧酸等脂环族多元羧酸类等。
作为多元羧酸酐类,可以列举例如邻苯二甲酸酐,均苯四甲酸酐,偏苯三甲酸酐,3,3’,4,4’-二苯甲酮四羧酸二酐等芳香族多元羧酸酐类;
衣康酸酐,琥珀酸酐,柠康酸酐,十二碳烯琥珀酸酐,丙三羧酸酐,马来酸酐,1,2,3,4-丁基四羧酸二酐等脂肪族多元羧酸酐类;
六氢邻苯二甲酸酐,3,4-二甲基四氢邻苯二甲酸酐,1,2,4-环戊三羧酸酐,1,2,4-环己三羧酸酐,环戊四羧酸二酐,1,2,4,5-环己四羧酸二酐,ハィミツク酸酐,ナジン酸酐等脂环族多元羧酸酐类;
乙二醇双偏苯三酸酯(トリメリティト)酸,甘油三偏苯三酸酯酐等含有酯基的羧酸酐类等。
作为上述的羧酸酐类,作为环氧树脂固化剂可以使用市售的。作为上述环氧树脂固化剂,可以列举例如商品名“アデカハ-ドナ-EH-700”(旭电化工业(株)制),商品名“リカシツド HH”(新日本理化(株)制),商品名“MH-700”(新日本理化(株)制)等。
上述固化剂可以单独也可以将两种以上组合使用
作为配制本发明的着色感光性树脂组合物的方法,可以列举例如,使溶剂(E)中并存颜料分散剂并使颜料等着色剂(A)分散,配制均匀粒径的着色剂(A)分散液,进一步,使溶解在溶剂中的粘结剂聚合物(B),光聚合性化合物(C),光聚合引发剂(D)和根据需要的其它的添加剂等溶解,将上述着色剂(A)与分散液混合,根据需要进一步添加溶剂的方法等。
如此得到的着色感光性树脂组合物,经过运输和保管提供给颜色滤光片的制造。在上述运输,保管(例如5℃)期间,通常,在一定温度下保存的,其温度通常为0~25℃,优选为5~10℃。从着色感光性树脂组合物的配制到提供给颜色滤光片的制造(例如23℃),这期间越短越好,着色感光性树脂组合物,从其配制开始的至少3个月期间,优选维持能形成与配制当时相同品质的颜色滤光片的性能。
另外,着色感光性树脂组合物的开发时,在其先行评价中,如果确认上述3个月期间的经时稳定性,开发的期间就变长。因此,进行的是将评价经时稳定性的温度从上述常规的温度,提高到例如40℃~60℃,加速经时变化,缩短保存时间评价的方法。
因此,作为上述经时稳定性的评价方法可以列举例如将着色感光性树脂组合物的粘度变化率用作指标的方法等。粘度变化率可以用下式1求出。
(式中,η0表示在开始保存前测定的粘度,η表示在一定温度下保存一定时间后测定的粘度。)
为了算出上述的粘度变化率,测定粘度。粘度,可以在一定的液温(例如23℃)下,例如使用E型粘度计コ-ンプレ-ト,在一定的转数(例如50rpm。)下测定。
粘度变化率优选在3%以下。如果在3%以下,由于能以与着色感光性树脂组合物刚配制后相同的性能、平滑性好、无异物地形成颜色滤光片,因此是优选的。
另外,本发明的着色感光性树脂组合物,通常将其封入容器中,提供给运输、保管。
作为使用本发明的着色感光性树脂组合物形成彩色滤光片图案的方法,可以列举例如,将本发明的着色感光性树脂组合物(例如红色)涂布到基板上,除去溶剂等挥发成分形成着色层,通过光掩膜使该着色层曝光、显像的方法等。
此处,作为基板,可以列举例如玻璃基板,硅基板,聚碳酸酯基板,聚酯基板,芳香族聚酰胺基板,聚酰胺亚胺基板,聚酰亚胺基板,Al基板,GaAs基板等表面平滑的基板等。
在这些基板上,可以实施通过硅烷偶合剂等化学品的药品处理,等离子处理,离子电镀处理,溅射处理,气相反应处理,真空蒸镀处理等前处理。
另外,在这些基板上,可以形成其它着色图案。
作为基板使用硅基板的情况下,在硅基板等的表面上可以形成电荷结合元件(CCD),薄膜晶体管(TFT)等。
为了在上述基板(包括形成其它着色图案的基板)上涂布着色感光性树脂组合物,优选的是,使用现有的旋转涂布和无液涂布、尤其是使用旋转涂布涂布到基板等上,然后通过加热使溶剂等挥发成分挥发。加热,通常在40℃~120℃左右,进行1~5分钟左右。
这样,在基板或形成了其它着色图案的基板上平滑性良好地形成着色感光性树脂组合物的固形成分的着色层。
形成的着色层,通过光掩膜并曝光、显像。
曝光使用i线(波长365nm)、h线、g线等,但优选使用i线(波长365nm)。i线(波长365nm)光源优选使用超高压水银灯(ゥシォ电机(株)社制;HB-75105AA OP1)灯,照射光量,通常为50~400mJ/cm2左右。
显像,通常通过在显像液中浸渍而实施。作为显像液,例如,可以列举氢氧化钠,氢氧化钾,碳酸钠,丁基萘磺酸钠,氢氧化四甲基铵(TMAH)等。特别地,优选使用以质量比率计含有0.05%的氢氧化钠、0.2%的丁基萘磺酸钠的显像液。
显像后,根据需要,用纯水等洗涤,然后,可以在180℃~240℃进行10~60分钟左右的加热处理。
这样,形成着色图案(1)(例如红色)。
然后,在着色图案(1)上,使用着色感光性树脂组合物(例如绿色),与上述同样地,形成着色图案(2)(例如绿色)。而且,在着色图案(2)上,使用着色感光性树脂组合物(例如蓝色),与上述同样地,形成着色图案(3)(例如蓝色)。这样,可以制造目的彩色滤光片。
通过在如上所述得到的彩色滤光片上,将经过ITO,定向膜,经过摩擦工序的基板和TFT基板通过隔板粘合,并注入液晶可以制造液晶显示装置。
实施例
上述对本发明的实施方式进行了说明,但上述公开的本发明的实施方式,终究只是例示,本发明的范围不限于这些实施方式。本发明范围包括,由权利要求的范围所表示的,以及与权利要求范围的记载等同的含义及范围内的所有变化。下面,通过实施例更详细地说明本发明,但本发明并不因这些实施例而被限制。
本实施例中使用的成分如下,下面是省略表示。
(A-1)着色剂:C.I.颜料红254
(B)粘结剂聚合物:甲基丙烯酸和甲基丙烯酸苄基酯共聚物[甲基丙烯酸单体和甲基丙烯酸苄基酯单体的比率为质量比(摩尔比)30∶70,酸值113,聚苯乙烯换算的重量平均分子量为30,000]
(C)光聚合性化合物:二季戊四醇六丙烯酸酯
(D-1)光聚合引发剂:2-甲基-2-吗啉代-1-(4-甲基硫代苯基)丙烷-1-酮
(D-2)光聚合引发剂:2,4-双(三氯甲基)-6-胡椒基-1,3,5-三嗪
(G-1)光聚合引发助剂:2,4-二乙基噻吨酮
(E-1)溶剂:丙二醇单甲基醚乙酸酯
(E-2)溶剂:4-羟基-4-甲基-2-戊酮
实施例1
[着色感光性树脂组合物1的配制]
将下述成分混合得到着色感光性树脂组合物1。
(A-1) 7.98质量份
聚酯系颜料分散剂 2.39质量份
(B) 5.40质量份
(C) 3.60质量份
(D-1) 0.54质量份
(D-2) 0.54质量份
(G-1) 0.54质量份
(E-1) 76.54质量份
(E-2) 2.37质量份
[粘度变化率]
着色感光性树脂组合物1的粘度变化率示于表1中。
[干燥异物]
在30mL螺旋式褐色瓶中封入20mL的着色感光性树脂组合物1并密闭,上下激烈振荡后,将上述褐色瓶在23℃保存1个月。将上述褐色瓶开封,在着色感光性树脂组合物中看不到干燥异物的沉降。另外在瓶的螺旋部分也没有看到干燥异物。
实施例2
[着色感光性树脂组合物2的配制]
将下述成分混合得到着色感光性树脂组合物2。
(A-1) 7.98质量份
聚酯系颜料分散剂 2.39质量份
(B) 5.40质量份
(C) 3.60质量份
(D-1) 0.54质量份
(D-2) 0.54质量份
(G-1) 0.54质量份
(E-1) 71.01质量份
(E-2) 7.90质量份
[粘度变化率]
着色感光性树脂组合物2的粘度变化率示于表1中。
[干燥异物]
除了用着色感光性树脂组合物2代替着色感光性树脂组合物1以外与实施例1同样地评价。在着色感光性树脂组合物中没有看到干燥异物的沉降,另外在瓶螺旋部分也确认没有看到干燥异物。
实施例3
[着色感光性树脂组合物3的配制]
将下述成分混合得到着色感光性树脂组合物3。
(A-1) 7.98质量份
聚酯系颜料分散剂 2.39质量份
(B) 5.40质量份
(C) 3.60质量份
(D-1) 0.54质量份
(D-2) 0.54质量份
(G-1) 0.54质量份
(E-1) 63.11质量份
(E-2) 15.80质量份
[粘度变化率]
着色感光性树脂组合物3的粘度变化率示于表1中。
[干燥异物]
除了用着色感光性树脂组合物3代替着色感光性树脂组合物1以外与实施例1同样地评价。在着色感光性树脂组合物中没有看到干燥异物的沉降,另外在瓶的螺旋部分也没有看到干燥异物。
实施例4
[着色感光性树脂组合物4的配制]
将下述成分混合得到着色感光性树脂组合物4。
(A-1) 7.98质量份
聚酯系颜料分散剂 2.39质量份
(B) 5.40质量份
(C) 3.60质量份
(D-1) 0.54质量份
(D-2) 0.54质量份
(G-1) 0.54质量份
(E-1) 47.31质量份
(E-2) 31.60质量份
[粘度变化率]
着色感光性树脂组合物4的粘度变化率示于表1中。
[干燥异物]
除了用着色感光性树脂组合物4代替着色感光性树脂组合物1以外与实施例1同样地评价。在着色感光性树脂组合物中没有看到干燥异物的沉降,另外在瓶的螺旋部分也确认没有看到干燥异物。
比较例1
[着色感光性树脂组合物5的配制]
将下述成分混合得到着色感光性树脂组合物4。
(A-1) 7.98质量份
聚酯系颜料分散剂 2.39质量份
(B) 5.40质量份
(C) 3.60质量份
(D-1) 0.54质量份
(D-2) 0.54质量份
(G-1) 0.54质量份
(E-1) 78.91质量份
[粘度变化率]
着色感光性树脂组合物5的粘度变化率示于表1中。
[干燥异物]
除了用着色感光性树脂组合物5代替着色感光性树脂组合物1以外与实施例1同样地评价。在着色感光性树脂组合物中没有看到干燥异物的沉降,但在瓶的螺旋部分看到有干燥异物。
比较例2
[着色感光性树脂组合物6的配制]
除了用4-羟基-4-甲基-2-戊酮代替丙二醇单甲基醚外,与实施例1同样地,得到着色感光性树脂组合物6。
[粘度变化率]
着色感光性树脂组合物6的粘度变化率示于表1中。
[干燥异物]
除了用着色感光性树脂组合物6代替着色感光性树脂组合物1以外与实施例1同样地评价。在着色感光性树脂组合物中没有看到干燥异物的沉降,但在瓶的螺旋部分看到有干燥异物。
表1
粘度变化率(%) | 干燥异物 | ||
40℃×1星期 | 23℃×1个月 | ||
实施例1 | 2.0 | 2.0 | 无 |
实施例2 | 2.8 | 2.5 | 无 |
实施例3 | 2.5 | 2.1 | 无 |
实施例4 | 2.9 | 2.5 | 无 |
比较例1 | 2.8 | 3.2 | 有 |
比较例2 | 10.4 | 6.2 | 有 |
工业上的可利用性
根据本发明,可以提供经时稳定性良好的着色感光性树脂组合物。本发明的着色感光性树脂组合物,由于经时稳定性优异,如果用于狭缝涂布,可以得到平滑性良好的涂膜。
Claims (8)
1、着色感光性树脂组合物,其特征在于在含有着色剂(A)、粘结剂聚合物(B)、光聚合性化合物(C)、光聚合引发剂(D)和溶剂(E)的着色感光性树脂组合物中,溶剂(E)含有丙二醇单甲基醚乙酸酯和4-羟基-4-甲基-2-戊酮。
2、权利要求1记载的组合物,其中着色感光性树脂组合物中的溶剂(E)的含量为70质量%以上95质量%以下。
3、权利要求1或2记载的组合物,其中溶剂(E)基本上是由丙二醇单甲基醚乙酸酯和4-羟基-4-甲基-2-戊酮构成的。
4、权利要求1~3中任意一项记载的组合物,其中溶剂(E)中的4-羟基-4-甲基-2-戊酮的含量为3质量%以上40质量%以下。
5、图案的形成方法,其特征在于将权利要求1~4中任意一项记载的组合物涂布到基板上,除去挥发成分形成着色层,通过光掩膜并将该着色层曝光、显像。
6、通过权利要求5记载的方法形成的图案。
7、彩色滤光片,其特征在于包含权利要求6记载的图案。
8、具备权利要求7记载的彩色滤光片的液晶显示装置。
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CN102126951A (zh) * | 2009-12-22 | 2011-07-20 | 株式会社Lg化学 | 可交联化合物以及包含所述可交联化合物的光敏组合物 |
CN101086619B (zh) * | 2006-06-08 | 2012-03-21 | 住友化学株式会社 | 彩色光敏树脂组合物 |
CN103309155A (zh) * | 2012-03-15 | 2013-09-18 | 住友化学株式会社 | 着色固化性树脂组合物 |
CN111399340A (zh) * | 2013-08-22 | 2020-07-10 | 东友精细化工有限公司 | 着色感光性树脂组合物、包含其的滤色器和显示装置 |
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US4877697A (en) * | 1988-05-26 | 1989-10-31 | Hoechst Aktiengesellschaft | Color filter array for liquid crystal display device |
US5882843A (en) * | 1994-11-15 | 1999-03-16 | Hoechst Japan Limited | Photosensitive resin composition for color filter production |
EP0902327A3 (en) * | 1997-09-09 | 2000-04-05 | JSR Corporation | Radiation sensitive composition |
JP2000095992A (ja) * | 1998-09-22 | 2000-04-04 | Dainippon Printing Co Ltd | 顔料分散剤及び感光性着色組成物 |
JP2002022925A (ja) * | 2000-07-11 | 2002-01-23 | Nippon Steel Chem Co Ltd | カラーフィルターの製造方法及び着色感光性樹脂組成物 |
JP2002049149A (ja) * | 2000-08-01 | 2002-02-15 | Fuji Photo Film Co Ltd | 電子線又はx線用ネガ型レジスト組成物 |
JP3956679B2 (ja) * | 2001-01-24 | 2007-08-08 | 住友化学株式会社 | 着色感光性組成物 |
JP4608796B2 (ja) * | 2001-03-28 | 2011-01-12 | 住友化学株式会社 | 着色感光性樹脂組成物 |
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Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
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CN101086619B (zh) * | 2006-06-08 | 2012-03-21 | 住友化学株式会社 | 彩色光敏树脂组合物 |
CN102126951A (zh) * | 2009-12-22 | 2011-07-20 | 株式会社Lg化学 | 可交联化合物以及包含所述可交联化合物的光敏组合物 |
CN102126951B (zh) * | 2009-12-22 | 2015-03-18 | 株式会社Lg化学 | 可交联化合物以及包含所述可交联化合物的光敏组合物 |
CN103309155A (zh) * | 2012-03-15 | 2013-09-18 | 住友化学株式会社 | 着色固化性树脂组合物 |
CN103309155B (zh) * | 2012-03-15 | 2018-12-28 | 住友化学株式会社 | 着色固化性树脂组合物 |
CN111399340A (zh) * | 2013-08-22 | 2020-07-10 | 东友精细化工有限公司 | 着色感光性树脂组合物、包含其的滤色器和显示装置 |
CN111399340B (zh) * | 2013-08-22 | 2024-01-30 | 东友精细化工有限公司 | 着色感光性树脂组合物、包含其的滤色器和显示装置 |
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KR101046889B1 (ko) | 2011-07-07 |
TW200422354A (en) | 2004-11-01 |
CN100351656C (zh) | 2007-11-28 |
KR20040048306A (ko) | 2004-06-07 |
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