CN1257434C - 感光性树脂组合物 - Google Patents
感光性树脂组合物 Download PDFInfo
- Publication number
- CN1257434C CN1257434C CNB031034152A CN03103415A CN1257434C CN 1257434 C CN1257434 C CN 1257434C CN B031034152 A CNB031034152 A CN B031034152A CN 03103415 A CN03103415 A CN 03103415A CN 1257434 C CN1257434 C CN 1257434C
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- Prior art keywords
- compound
- acid
- base
- photosensitive polymer
- polymer combination
- Prior art date
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- 230000000007 visual effect Effects 0.000 description 1
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Abstract
一种具有下述(A)-(E)并实质上不含有着色剂的感光性树脂组合物,(A)使下述(a)~(d)化合物反应得到的反应产物,(a)具有多个异氰酸酯基的化合物,(b)1价的醇,(c)具有2~3个选自-OH基,-NH2基和-NHR基(R表示碳数1~4的烷基),可以具有至少1个选自-O-基,-COO-基,-CONH-基,-S-基和-SO2-基的基团的化合物,(d)3级胺化合物,(B)粘合剂聚合物,(C)光聚合性化合物,(D)光聚合性引发剂和(E)溶剂。通过将上述感光性树脂组合涂布在基板或在基板上形成的固体的有色感光性树脂组合物层上,从涂布的感光性树脂组合物层除去挥发成分,介入光掩膜并将除去挥发成分的层曝光,显像可形成图案,并可制作滤色片和组装上述滤色片的液晶显示装置。
Description
技术领域
本发明涉及感光性树脂组合物,特别是用于滤色片的无色透明材料,例如适宜形成外敷层,光垫片,为调整有色图案膜厚的无色透明涂布剂等的滤色片的形成中使用的无色透明感光性树脂组合物,和用它们形成的滤色片,以及,使用上述滤色片的液晶显示装置。
背景技术
近年来,在液晶元件中组装用于色分解的滤色片的液晶显示元件有各种方案。此处,所谓滤色片,是指存在由将在光透过性基板上形成的红,绿,蓝3原色的象素形成图象的多个图象构成的、在各象素间,为了提高显示对比,设计具有一定宽度的遮光区域(黑色基体)的情况。另外,也有配备外敷层或光垫片,为调整有色图案膜厚的无色涂布剂,透明电极的。
作为构成这样的象素,黑色基体的树脂组合物,以及作为用于外敷层或光垫片,为调整有色图案膜厚的无色透明涂布剂(下面称为无色透明涂布剂。)的树脂组合物,过去,使用含有硅氧烷聚合物,聚酰亚胺树脂,环氧树脂,丙烯酸树脂等的热固化性树脂或感光性树脂等的树脂组合物。
但是,将含有上述热固化树脂的现有组合物用于无色透明涂布剂等时,由于象素的表面上发生粗糙,存在由于光散射透光率降低,难以具有作为无色透明涂布剂机能的问题。另外,上述组合物中,由于热固化性树脂的固化物,容易产生粒状异物等的涂布疵点,一旦发生粒状异物等的涂布疵点,它们就成为滤色片中的异物,使例如通过彩色液晶显示装置显示的彩色图像或通过彩色固体摄像元件拍摄的彩色图像等的品质恶化,存在难以得到良好滤色片和液晶显示装置的问题。
另外,含有上述的感光性树脂的现有组合物中,在制成透明层时,存在析像度变差的问题。如果析像度变差,在适合半透明型滤色片膜厚用部件中使用时,反射部分和透光部分交界处颜色不同,这样使通过彩色液晶显示装置显示的彩色图像或通过彩色固体摄像元件拍摄的彩色图像等的品质降低。
另外,使用现有的含有热固化性树脂或感光性树脂的组合物时,如果作为外敷层材料使用,不仅面内均一性恶化,而且基板边缘部分的膜厚变厚,如果作为光垫片使用,由于外壳缝隙变得不均一发生显示斑点,如果作为为调整有色图案膜厚的无色透明涂布剂使用,由于膜厚变化存在颜色目视性不同的问题。
发明内容
本发明的目的是提供没有表面粗糙和透明性降低,也没有涂布疵点,并且析像度良好,基板边缘部分的平坦性良好的感光性树脂组合物,使用上述组合物的滤色片和液晶显示装置。
因此本发明者,深入研究的结果,发现如果使用含有使特定的化合物反应得到的产物的感光性树脂组合物形成图案,可以没有表面粗糙和由于在400-780nm的透光率高而透明性不降低,没有涂布疵点,析像度好,基板边缘部分的平坦性良好,从而完成了本发明。
因此,本发明提供含有
(A)使下述(a)~(d)化合物反应得到的反应产物,
(a)具有多个异氰酸酯基的化合物、
(b)1价的醇、
(c)具有2~3个选自-OH基,-NH2基和-NHR基(R表示碳数1~4的烷基)的基团,可以具有至少1个选自-O-基,-COO-基,-CONH-基,-S-基和-SO2-基的基团的化合物、和
(d)3级胺化合物,
(B)粘合剂聚合物,
(C)光聚合性化合物,
(D)光聚合性引发剂和,
(E)溶剂并且实质上不含有着色剂的感光性树脂组合物;其中相对于每100质量份(B)粘合剂聚合物和(C)光聚合性化合物的总量,含有0.5质量份以上50质量份以下(A)反应产物,0.1质量份以上20质量份以下(D)光聚合性引发剂,并且相对于感光性树脂组合物的固形成分,(B)粘合剂聚合物占质量比为5%以上90%以下,(C)光聚合性化合物占质量比为5%以上90%以下。将上述感光性树脂组合涂布在基板或在基板上形成的固体的着色感光性树脂组合物层上,从涂布的感光性树脂组合物层除去挥发成分,介入光掩膜并将除去挥发成分的层曝光并显像的图案形成方法;含有通过上述方法形成的图案的滤色片和组装上述滤色片的液晶显示装置。
优选方案的详细说明
本发明中使用的(A)反应产物,是使
(a)具有多个异氰酸酯基的化合物、
(b)1价醇、
(c)具有2~3个选自-OH基,-NH2基和-NHR基(R表示碳数1~4的烷基)的基团,可以具有至少1个选自-O-基,-COO-基,-CONH-基,-S-基和-SO2-基的基团的化合物和
(d)三级胺化合物反应得到的产物
作为本发明中使用的(A)(a)具有多个异氰酸酯基的化合物,可以列举选自例如芳香族聚异氰酸酯,脂肪族聚异氰酸酯和脂环式聚异氰酸酯中的至少1种,优选使至少1种选自2,4-甲苯撑二异氰酸酯,2,5-甲苯撑二异氰酸酯,二苯基甲烷异氰酸酯,聚亚甲基聚苯基聚异氰酸酯,联甲苯胺异氰酸酯,萘二异氰酸酯,六亚甲基二异氰酸酯,异佛尔酮二异氰酸酯,苯撑二甲基二异氰酸酯,氢化苯撑二甲基二异氰酸酯和二环己基甲烷二异氰酸酯反应得到的化合物等,进一步优选地,优选选自至少一种例如下述化合物(a-1)~(a-8)。
作为本发明中使用的(A)(b)1价醇,可以列举
Y-CH2OH所表示的化合物。[式中,Y表示选自下列基团:
(1)碳数7~30的脂肪族烃基(该脂肪族烃基的氢原子中的至少1个,可以被至少1种选自卤素原子和芳基的基团取代。)
(2)碳数6~30的脂环式烃基(该脂环式烃基的氢原子中的至1个,可以被至少1种选自卤素原子和芳基的基团取代。),
(3)脂肪族烃基中的至少1个亚甲基可以被-O-或-COO-基取代的取代脂肪族烃基(该基团中的至少1个氢原子可以被卤素原子取代,但-O-间,-COO-间或者-COO-和-O-间不相邻,与OH基键合的亚甲基不被-O-基或-COO-基取代。),
(4)可以有脂肪族烃基的脂环式烃基的环上或脂肪族烃基上的亚甲基中的至少1个被-O-基或-COO-基取代的取代脂环式烃基(该基团中的至少1个氢原子可以被卤素原子取代,但-O-间,-COO-间或者-O-基和-COO-基间不相邻。)和
(5)具有至少1个脂肪族烃基的芳香族烃基的该脂肪族烃基上的至少1个亚甲基被-O-和-COO-取代的取代芳香族烃基(该芳香族烃基可以被卤素原子取代,但-O-间,-COO-间或者-O-基和-COO-基间不相邻。)。但是Y不包含氮原子。]
作为上述化合物,可以列举例如辛醇,壬醇,癸醇,十一烷醇,十二烷醇,月桂基醇,十八烷醇,十七氟癸醇,聚醚,聚酯和其混合物等。
作为上述聚醚,可以列举例如聚乙二醇或聚丙二醇等。作为上述聚酯,可以列举例如以具有1个-OH基的化合物和丙内酯,戊内酯,己内酯这样的内酯或其取代的衍生物等为原料开环聚合反应成聚酯的化合物等。作为上述具有1个-OH基的化合物,可以列举例如正丙醇,正戊醇,正己醇,正庚醇,正辛醇,正壬醇,正癸醇,油醇,亚油醇,环己醇,苯基乙醇,或新戊醇等长链饱和和不饱和醇,或者上述醇的氟代的碳数4~30,优选4~14的1价醇。
作为本发明中使用的(A)(c)具有2~3个选自-OH基、-NH2和-NHR(R定义同前。)可以有至少1个选自-O-基、-COO-基-CONH-基、-S-基和-SO2-基的化合物、可以列举
G-(E)n所表示的化合物等。[式中,G表示选自脂肪族烃基,脂环式烃基和芳香族烃基的基团。
上述的G,各自独立地,在烃基内部至少有1个亚甲基可以被-O-基,-COO-基,-CONH-基,-S-基或-SO2-取代。
n表示2或3。
E表示选自-OH基,-NH2基和-NHR基(R定义同前。)的基团,E相互可以相同也不同。]。
作为上述化合物,可以列举例如丁二醇、己二醇、环己基二甲醇、新戊二醇、乙二醇、丙二醇等碳数2~12的二醇,甘油、三羟甲基丙烷等碳素2~12的三醇,2,6-甲苯二胺等碳素2~12的二胺,二乙醇胺等碳数2~12的二烷醇胺,乙醇胺等碳数2~12的单烷醇胺,N-甲基二乙醇胺等烷基取代的二烷醇胺,脂肪族的二烷醇胺盐,硫代二乙二醇等二羟基烷基硫化物,二(4-羟基苯基)砜等二羟基烷基砜等。
作为本发明中使用的(A)(d)三级胺化合物,可以列举
Z-Q所表示的化合物。[式中,
Z表示含有为形成三级胺的基团的碳数2~10个的脂肪族烃基,优选脂肪族烃基中的甲基被2个氨基取代的碳素2~10的三级胺取代脂肪族烃基
或
至少含有1个氮原子的杂环式烃基(但是上述氮原子不与氢键合),优选含氮杂环基(但是上述氮原子仅与碳原子键合。)。
上述杂环式烃基可以有碳数1~10个的亚烷基插入并与Q基键合。
Q表示选自-OH基,-NH2基,-NHR(R定义同前。)和-SH基的基团。]
作为上述化合物,可以列举例如N,N-二甲基-1,3-丙二胺,4-(2-氨基乙基)吡啶,2-氨基-6-甲氧基苯并噻唑,4-(氨基甲基)吡啶,N,N-二烯丙基三聚氰胺,3-氨基-1,2,4-三唑,1-(3-氨基丙基)咪唑,4-(2-羟基乙基)吡啶,1-(2-羟基乙基)咪唑,3-巯基-1,2,4-三唑,N,N-二乙基-1,4-丁二胺,1-(2-氨基乙基)哌啶,2-(1-吡咯烷基)乙胺,4-氨基-2-甲氧基吡啶,2-二甲基氨基乙醇,1-(2-羟基乙基)哌啶,4-(2-羟基乙基)吗啉,2-巯基嘧啶,2-巯基苯并咪唑等。特别优选N,N-二甲基-1,3-丙二胺,4-(2-氨基乙基)吡啶,2-氨基-6-甲氧基苯并噻唑,4-(氨基甲基)吡啶,N,N-二烯丙基三聚氰胺,3-氨基-1,2,4-三唑,1-(3-氨基丙基)咪唑,4-(2-羟基乙基)吡啶,1-(2-羟基乙基)咪唑,和3-巯基-1,2,4-三唑。
作为使上述(a)~(d)的成分反应的方法,可以列举下列的方法。
(1)首先使(a)和(b)反应。在所添加的(a)所表示化合物的异氰酸酯基中,添加与15~40%,优选20~40%,特别优选20~35%反应量的(b)所表示的化合物并反应。
(2)其次,将上述(1)的反应所得产物中添加以未反应的异氰酸酯基合计与(1)的反应前的异氰酸酯基的至少40%且作多75%,优选45~65%,特别优选45~55%的量的(c)所表示的化合物并反应。
(3)进一步地,在上述(2)反应所得产物中,添加相当于相对于未反应残余的异氰酸酯基至少1分子比例量的(d)所表示的化合物并反应。
作为使上述(a)~(d)成分反应得到的(A)反应产物,可以使用例如在特开平62-70459号公报等上例示的化合物。(A)反应产物可以是市售的,可以使用该市售产品。作为市售产品,可以列举Disperbyk-115,Disperbyk-160,Disperbyk-161,Disperbyk-162,Disperbyk-163,Disperbyk-164,Disperbyk-166,Disperbyk-167,Disperbyk-169,Disperbyk-170,Disperbyk-171,Disperbyk-174,Disperbyk-182(均由BYKChemie社制造)等,其中优选Disperbyk-161,Disperbyk-170。
上述反应产物的含量,相对于100质量份(B)粘合剂聚合物和(C)光聚合性化合物的总量,通常为0.5质量份以上50质量份以下,优选1质量份以上40质量份以下,特别优选2质量份以上30质量份以下。如果在0.5质量份以上50质量份以下,表面不粗糙,未曝光部分到显像液中的溶解性良好,析像度也优异的倾向,因此是优选的。
作为本发明中使用的(B)粘合剂聚合物,可以使用丙烯酸系共聚物,例如,可以列举含有羧基的单体和与其可共聚的其它单体的共聚物等。
作为含有羧基的单体,可以列举例如不饱和单羧酸,或不饱和二羧酸,不饱和三羧酸等不饱和多元羧酸等分子中至少有1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,桂皮酸等。作为不饱和二羧酸,可以列举例如马来酸,富马酸,衣康酸,甲基马来酸,中康酸等。不饱和多价羧酸,其酸酐,具体地可以是马来酸酐,衣康酸酐,甲基马来酸酐等。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,具体地,可以列举例如琥珀酸单(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,可以是其两末端二羧基聚合物的单(甲基)丙烯酸酯,具体地可以列举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,可以分别单独或2种或以上混合使用。
作为与上述含有羧基的单体可共聚的其它单体,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,邻乙烯基苄基甲基醚,间乙烯基苄基甲醚,对乙烯基苄基甲基醚,邻乙烯基苄基缩水甘油醚,间乙烯基苄基缩水甘油醚,对乙烯基苄基缩水甘油醚,茚等芳香族乙烯化合物;
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,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,丙烯酸苯基酯,甲基丙烯酸苯基酯,丙烯酸2-甲氧基乙酯,甲基丙烯酸2-甲氧基乙酯,丙烯酸2-苯氧基乙基酯,甲基丙烯酸2-苯氧基乙基酯,丙烯酸甲氧基二乙二醇酯,甲基丙烯酸甲氧基二乙二醇酯,丙烯酸甲氧基三乙二醇酯,甲基丙烯酸甲氧基三乙二醇酯,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,丙烯酸异冰片酯,甲基丙烯酸异冰片酯,丙烯酸二环戊二烯酯,甲基丙烯酸二环戊二烯酯,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;
乙烯基甲醚,乙烯基乙醚,丙烯基缩水甘油醚等不饱和醚类;
丙烯腈,甲基丙烯腈,α-氯丙烯腈,氰化的乙烯叉等氰化的乙烯基化合物;
丙烯酰胺,甲基丙烯酰胺,α-氯丙烯酰胺,N-2-羟基以及丙烯酰胺,N-2-羟基以及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,氯戊二烯等脂肪族共轭二烯类;
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,聚硅氧烷等聚合物分子链的末端上具有单丙烯酰基或单甲基丙烯酰基的大单体类等。这些单体可以分别单独或2种或以上混合使用。
上述共聚物中的含有羧基的单体单位的含量,质量比率通常为10~50质量%,优选15~40质量%,特别优选25~40质量%。
上述的含有羧基的单体单位的含量如果在10~50质量%,对于显像液的溶解性良好,显像时有图案正确形成的倾向,因此是优选的。
作为上述丙烯酸聚合物,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)丙烯酸甲酯大单体共聚物,(甲基)丙烯酸/(甲基)丙烯酸苄基酯/聚苯乙烯大单体共聚物,(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-苯基马来酰亚胺共聚物,(甲基)丙烯酸/琥珀酸单(2-丙烯酰氧基乙基)/苯乙烯/(甲基)丙烯酸苄基酯/N-苯基马来酰亚胺共聚物、苯基马来酰亚胺共聚物、(甲基)丙烯酸/琥珀酸单(2-丙烯酰氧基乙酯)/苯乙烯/(甲基)丙烯酸烯丙酯/N-苯基马来酰亚胺共聚物,(甲基)丙烯酸/(甲基)丙烯酸苄基酯/N-苯基马来酰亚胺/苯乙烯/甘油单(甲基)丙烯酸酯共聚物等。而且,所谓(甲基)丙烯酸酯表示丙烯酸酯和甲基丙烯酸酯。
其中,特别优选(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/苯乙烯共聚物等。
上述丙烯酸系共聚物,其聚苯乙烯换算质量平均分子量通常为3,000~400,000,优选为5,000~100,000,特别优选为20,000~40,000。分子量如果为3,000~400,000,涂膜硬度提高,残膜率也高,未曝光部分对显像液的溶解度良好,析像度也有提高的倾向,因此是优选的。
另外,酸价通常为30~250,优选60~180,特别优选为90~160。
上述酸价,如果为30~250,对显像液的溶解度提高且对未曝光部分也容易溶解,另外高感光度化在显像时图案残留的残膜率有提高的倾向,因此是优选的。
此处酸价是指测定中和1g丙烯酸系聚合物所必须的氢氧化钾的量(mg)的值,通常通过用氢氧化钾水溶液滴定可以求出。
上述粘合剂树脂,相对于感光性树脂组合物的固形成分(除组合物中溶剂外的合计量。以下同。),质量比率通常在5质量%以上90质量%以下,优选为10质量%以上80质量%以下,特别优选20质量%以上70质量%以下的范围内使用。
上述的粘合剂树脂的含量,如果在5质量%以上90质量以下,图案中难有凹陷,粘合性有变良好的倾向,另外析像度和残膜率有提高的倾向,因此是优选的。
本发明中使用的(C)光聚合性化合物,是通过由光照射由光聚合引发剂产生的活性自由基,酸等而聚合的化合物,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,优选具有4个或以上的多官能的光聚合性化合物。作为4官能或以上的多官能的光聚合性化合物,可以列举例如季戊四醇(pentaerg thritol)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。这些光聚合性化合物,可以分别单独或2种或以上联合使用,其含量相对于着色感光性树脂组合物中固形成分,质量比率通常为5质量%以上90质量%以下,优选10质量%以上80质量%以下,特别优选20质量%以上70质量%以下。
上述的,光聚合性化合物的含量,如果为5质量%以上90质量%以下,固化充分残膜率提高,图案难进入凹陷有粘合性良好的倾向,因此是优选的。
作为本发明中使用的(D)光聚合性引发剂,可以列举通过光照射产生活性自由基的活性自由基产生剂,产生酸的酸产生剂等。作为活性自由基产生剂,可以列举例如苯乙酮系化合物,三嗪系化合物,苯偶姻系化合物,二苯甲酮系化合物,噻吨酮系化合物等。
作为苯乙酮化合物,可以列举例如二乙氧基苯乙酮,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-丙氧基环己基苯酮,2-甲基-2-吗啉-1-(4-甲基硫代苯基)丙烷-1-酮,2-苄基-2-二甲基氨基-1-(4-吗啉基苯基)丁烷-1-酮,2-羟基-2-甲基-1-[4-(1-甲基乙烯基)苯基]丙烷-1-酮和其寡聚物等。
作为三嗪化合物,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-胡椒基-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。
作为苯偶姻化合物,可以列举苯偶姻,苯偶姻甲基醚,苯偶姻乙基醚,苯偶姻丙基醚,苯偶姻丁基醚等。
作为二苯甲酮化合物,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。
作为其它的活性自由基,也可以列举例如2,4,6-三甲基苯甲酰基二苯基膦氧化物,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,樟脑醌,苯基乙醛酸甲酯,环戊二烯钛(チタノセン)化合物等。
作为酸产生剂,可以列举4-羟基苯基二甲基锍对-甲苯磺酸盐,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盐,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盐,三苯基锍六氟锑酸盐,苯基碘鎓对甲苯磺酸盐,二苯基碘鎓六氟锑酸盐等鎓盐类,硝基苄基对甲苯磺酸盐类,苯偶姻对甲苯磺酸盐类等。
另外,作为活性自由基产生剂的上述化合物中,也有可以同时产生活性自由基和酸的化合物,例如三嗪系化合物也可以作为酸产生剂使用。
这些光聚合引发剂可以分别单独或2种或以上联合使用。作为上述光聚合引发剂,优选使用苯乙酮系化合物,特别是2-甲基-2-吗啉-1-(4-甲基硫代苯基)丙烷-1-酮等。
(D)光聚合引发剂的含量,相对于100质量份(B)粘合剂聚合物和(C)光聚合性化合物的总量通常为0.1质量份以上20质量份以下,优选1质量份以上15质量份以下。如果光聚合引发剂的含量为0.1质量份以上20质量份以下,高感光度化曝光时间缩短生产性提高,另一方面过了高感光度析像度有不变差的倾向,因此是优选的。
本发明中可以添加光聚合引发助剂,光聚合引发助剂是与(D)光聚合引发剂联合使用的,是为促进(C)光聚合性化合物的聚合而含有的化合物。作为光聚合引发助剂,可以列举例如胺系列化合物,烷氧基蒽系列化合物等。
作为胺系列化合物,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)二苯甲酮,(通称为米希勒酮),4,4’-双(二乙基氨基)二苯甲酮(市售的为保土谷化学工业(株)制的“EAB-F”)4,4’-双(乙基甲基氨基)二苯甲酮等。
作为烷氧基蒽系列化合物,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。
使用这些光聚合引发助剂时,其使用量,每1摩尔光聚合引发剂通常在10摩尔以下,优选在0.01摩尔以上5摩尔以下。
作为本发明中使用的(E)溶剂,可以列举例如醚类,芳香族烃类,酮类,酯类,酰胺类等。
作为醚类,四氢呋喃,四氢吡喃,1,4-二噁烷,乙二醇单甲醚,乙二醇单乙醚,乙二醇但丙醚,乙二醇单丁醚,二乙二醇单甲醚,二乙二醇单乙醚,二乙二醇单丁醚,二乙二醇二甲醚,二乙二醇二乙醚,二乙二醇二丙醚,二乙二醇二丁醚,丙二醇单甲醚乙酸酯,丙二醇单乙醚乙酸酯,丙二醇单丙醚乙酸酯,甲基乙二醇乙醚乙酸酯、乙基乙二醇乙醚乙酸酯,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。
作为芳香族烃基,可以列举例如苯,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-戊酮,环己酮等。
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,羟基乙酸甲酯,羟基乙酸乙酯,羟基乙酸丁酯,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-羟基丙酸乙酯,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-羟基丁酸甲酯,2-羟基丁酸乙酯,乙酸3-甲氧基丁酯,乙酸3-甲基-3-甲氧基丁酯等。作为酰胺类,可以列举例如N,N-二甲基磺酰胺,N,N-二甲基乙酰胺等。
作为可在本发明中使用的溶剂除上述之外,可以列举例如N-甲基吡咯烷酮,二甲基亚砜等。
这些溶剂中特别优选使用,3-甲氧基丙酸甲酯,3-甲氧基丙酸甲酯,3-乙氧基丙酸乙酯,乙基乙二醇乙醚乙酸酯,乳酸乙酯,二乙二醇二甲基醚,乙酸丁酯,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,2-庚酮等。
上述溶剂,可以分别单独或2种或以上联合使用,感光性树脂组合物中的上述溶剂的含量,质量比率,通常在50质量%以上90质量%以下,优选60质量以上85质量以下。溶剂含量如果在50质量%以上90质量%以下,平坦性良好,作为滤色片时可以得到充分的色浓度,因此是优选的。
作为本发明中使用的(F)表面活性剂,可以使用至少1种选自聚硅氧烷系列表面活性剂,氟系列表面活性剂和具有氟原子的聚硅氧烷表面活性剂。
作为聚硅氧烷表面活性剂,可以列举DC3JP,SH7PA,DC11PA,SH21PA,SH28PA,29SHPA,SH30PA,SH30PA(东レ·ダゥコ-ニング·シリコ-ン(株)制),聚醚变性聚硅油SH8400(商品名:东レ·ダゥコ-ニング·シリコ-ン(株)制),KP321,KP322,KP323,KP324,KP326,KP340,KP341(信越シリコ-ン制),TSF400,TSF401,TSF410,TSF4300,TSF4440,TSF4445,TSF4446,TSF4452,TSF4460东芝(株)制)等。
作为氟系列表面活性剂,可以列举Florinat(登记的商标)FC430,同FC431,(住友Three M(株)制),Megafuatsuc(登记商标)F142D,同F171,同F172,同F173,同F177,同F183,同R30(大日本油墨化学工业(株)社制),Efutotsubu(登记商标)EF301,同EF303,同EF351,同EF352,(新秋田化成(株)制),Safuron(登记商标)S381,同S382,同SC101,同SC105(旭硝子(株)制,E5844,(ダィキンファィンケミカル制)BM-1000,BM-1100(均为商品名:BMChemie社制)等。
作为具有氟原子的聚硅氧烷系列表面活性剂,可以列举Megafuatsuc(登记商标)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,可以单独或2种以上组合使用。
本发明的感光性树脂组合物含有表面活性剂时,其含量相对于100质量份除(F)表面活性剂外感光性树脂组合物通常为0.0001质量份以上0.6质量份以下的范围内。
表面活性剂的含量如果在0.0001质量份以上0.6质量份以下,难以出现皱纹,有基板边缘部分的膜厚不变得过厚的倾向,因此是优选的。
本发明的感光性树脂组合物,可以含有无色填充颜料,填充剂,除(A)反应产物和(B)粘合剂聚合物以外的高分子化合物,粘合促进剂,抗氧化剂,光稳定剂,抗凝剂,有机酸,有机氨基化合物,固化剂等添加剂。
作为无色填充颜料,可以列举例如重晶石粉(BaSO4),沉淀性硫酸钡(BaSO4),碳酸钡(BaCO3)、碳酸钙粉(CaCO3),硅粉(SiO2),碱性碳酸镁(MgCO3),氧化铝胶(Al2O3·XH2O或Al(OH)3),珠光白(Al(OH)3+BaSO4),缎光白(BaSO4+Al(OH)3)等。
本发明的感光性树脂组合物中实质上不含有染料,颜料等着色剂。如果含有着色剂,形成滤色片时,在各色像素部分会发生混色,表示特性有变恶化的倾向。但是,构成本发明的感光性树脂组合物的成分和可以添加的成分中,虽然有例如光聚合引发剂或光聚合引发助剂等带黄色或蓝色的,但由于不影响本发明效果,因此本发明中这些成分并不被认为是着色剂。
作为填充剂,可以列举例如玻璃,氧化铝,硅胶等微粒。
作为除(A)反应产物和(B)粘合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,聚丙烯酸氟烷基酯等。
作为粘合促进剂,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)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-氨基丙基三甲氧基硅烷,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-环氧乙烷环己基)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-甲基丙烯酰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’-硫代双(6-叔丁基-3-甲基苯酚),2,6-二叔丁基-4-甲基苯酚等。
作为光稳定剂,可以列举例如紫外线吸收剂或受阻(hindered)胺系列光稳定剂等。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-辛氧基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-己氧基苯酚等三嗪系等,可以添加它们的混合物。作为受阻胺系光稳定剂,可以列举例如双(2,2,6,6-四甲基-4-哌啶基)癸二酸酯,双(1,2,2,6,6-五甲基-4-哌啶基)癸二酸酯,2,2,6,6-四甲基哌啶基硬脂酸酯,聚[[6-[1,1,3,3-四甲基丁基]氨基]-1,3,5-三嗪-2,4-二基][2,2,6,6-四甲基-4-哌啶基]亚氨基]-1,6-己二基[2,2,6,6-四甲基-4-哌啶基]亚氨基]]等,可以添加它们的混合物。另外,可以将紫外线吸收剂和受阻胺系光稳定剂联合使用。
作为抗凝剂,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,三甲基乙酸,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,巴西二酸,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,环己基二羧酸,衣康酸,柠康酸,马来酸,富马酸,中康酸等脂肪族二羧酸类;丙三羧酸,乌头酸,樟脑三酸等三羧酸类;苯甲酸,甲苯甲酸,枯茗酸,二甲基苯甲酸,莱林酸酸等芳香族单羧酸类;邻苯二甲酸,间邻苯二甲酸,对邻苯二甲酸等芳香族二羧酸类;偏苯三酸,均苯三甲酸,苯偏四甲酸,苯均四酸等芳香族多羧酸类。
作为有机胺化合物,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,正十一烷胺,正十二烷胺等单烷基胺类;
环己基胺,2-甲基环己基胺,3-甲基环己基胺,4-甲基环己基胺等单环烷基胺类;甲基乙基胺,二甲基胺,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;甲基环己基胺,乙基环己基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,二甲基正丙基胺,二乙基正丙基胺,甲基正丙基胺,乙基正丙基胺,三正丙基胺,三异丙基胺,三正丁基胺三异丁基胺,三仲丁基胺,三叔丁基胺,三正戊基胺,三正己基胺等三烷基胺类;二甲基环己基胺,二乙基环己基胺等二烷基单环烷基胺类;
甲基二环己基胺,乙基二环己基胺,三环己基胺等单烷基二环烷基胺类;2-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,二正己醇胺等二烷醇胺类;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-丙二醇等氨基烷二醇类;4-氨基-1,2-环己基二醇,4-氨基-1,3-环己基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-氨基异乙酸,三氨基异乙酸,2-氨基戊酸,5-氨基戊酸,6-氨基己酸,1-氨基环丙烷羧酸,1-氨基环己烷羧酸,4-氨基环己烷羧酸等氨基羧酸类;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,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;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等。
作为固化剂,可以列举例如通过加热可以与(B)粘合剂聚合物中的羧基反应并使粘合剂聚合物交联的化合物。另外,可以列举可以单独聚合使有色图案固化的化合物。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。
作为环氧化合物,可以列举例如双酚A系列环氧树脂,氢化双酚A系列环氧树脂,双酚F系列环氧树脂,氢化双酚F系列环氧树脂,酚醛型环氧树脂,其它芳香族环氧树脂,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或,这些环氧树脂的溴化衍生物,环氧树脂和其溴化衍生物之外的脂肪族,脂环族或芳香族环氧化合物,丁二烯(共)聚合物的环氧化合物,异戊二烯(共)聚合物的环氧化合物,缩水甘油(甲基)丙烯酸酯(共)聚合物,三缩水甘油异氰酸酯等。
作为氧杂环丁烷化合物,可以列举例如碳酸酯双氧杂环丁烷,亚二甲苯氧杂环丁烷,己二酸酯双氧杂环丁烷,对苯二酸酯双氧杂环丁烷,环己二酸双氧杂环丁烷等。
本发明的感光性树脂组合物,含有作为固化剂的环氧化合物,氧杂环丁烷化合物等时,可以含有可使环氧化合物的环氧基,氧杂环丁烷化合物的氧杂环丁烷骨架闭环聚合的化合物。作为前述化合物,可以列举例如多元羧酸类,多元羧酸酐类,酸产生剂等。
作为多元羧酸类,可以列举例如邻苯二甲酸,3,4-二甲基邻苯二甲酸,间苯二甲酸,对苯二甲酸,苯均四酸,偏苯二酸,1,4,5,8-萘四羧酸,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-丁烷四羧酸,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。
作为多元羧酸酐类,可以列举例如邻苯二甲酸酐,苯均四酸酐,偏苯三酸酐,3,3’,4,4’-二苯甲酮四羧酸二酸酐等芳香族多元羧酸酐类;衣康酸酐,琥珀酸酐,柠康酸酐,十二烯基琥珀酸酐,丙三羧酸酐,马来酸酐,1,2,3,4-丁烷四羧酸二酸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-环戊烷三羧酸酐,1,2,4-环己烷三羧酸酐,环戊烷四羧酸二酸酐,1,2,4,5-环己烷四羧酸二酸酐,ハィミック酸酐,ナジン酸酐等脂环族多元羧酸酐类;乙二醇双偏苯三酸酯酸,甘油三偏苯三酸酯酸酐等含有酯基的羧酸酐类。
作为羧酸酐类,可以使用作为环氧树脂固化剂销售的。作为环氧树脂固化剂,可以列举例如商品名“ァデカハ-トナ-EH-700”旭电化工业(株)制),商品名“リカシッドHH”(新日本理化(株)制),商品名“MH-700”(新日本理化(株)制)等。上述固化剂可以分别单独或2种或以上组合使用。
作为使用本发明的感光性树脂组合物形成图案的方法,具体地,可以列举可以将本发明的感光性树脂组合物在基板上或基板上预先形成的固体着色感光性树脂组合物层(下面将其称为基板等)上涂布,从涂布了感光性树脂组合物层除去溶剂等挥发性成分,插入光掩膜并将除去挥发成分的层曝光后,显像的方法。
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,聚酰亚胺基板等表面平坦的基板。这些基板,可以实施通过硅烷偶合剂等药品的药品处理,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。使用硅基板作为基板时,可以在上述硅基板等表面形成电荷键合元件(CCD),薄膜晶体三极管(TFT)等。
在上述基板上涂布感光性树脂组合物时,例如可以将本发明感光性树脂组合物用旋转涂布法(旋转涂布法),流延涂布法,滚筒涂布法,切削和旋转涂布法等常规的涂布方法涂布在基板等上,然后可以通过加热挥发溶剂等挥发成分。这样,在基板等上形成由感光性树脂组合物的固形成分形成的层。
其次,将由感光性树脂组合物的固形成分形成的层(下面将其称为感光性树脂组合物层。)曝光。曝光中,插入光掩膜并可以照射光线。作为光线,通常可以使用称为g线(波长436nm),i线(波长365nm)的紫外线。光线照射插入光掩膜,此处光掩膜,是在玻璃基板表面设计遮蔽光线的遮光层。玻璃板中未设计遮光层的部分光线可以穿透的透光部分,根据该透光部分图案的图案感光性树脂组合物层曝光,产生未照射光线的未照射区域和照射光线的照射区域。照射区域中的光线的照射量,根据(B)粘合剂聚合物的质量平均分子量,单体比,含量,(C)光聚合性化合物的种类和含量,(D)光聚合引发剂的种类或含量,光聚合引发助剂的种类或含量等适宜地选择。
曝光后,显像。显像,例如可以将曝光后的感光性树脂组合物层与显像液接触,具体地,将在其表面上形成感光性树脂组合物层的状态的基板浸渍在显像液中。作为显像液,可以列举例如碳酸钠,碳酸钾,氢氧化钠,氢氧化钾,氢氧化四甲基铵等碱性化合物的水溶液等。通过显像,将感光性树脂组合物层中光线没照射的未照射区域除去。另一方面,将光线照射区域直接残留构成图案。
显像后,通常通过水洗,干燥,可以得到目的图案。干燥后,可以加热。通过将图案加热固化,其机械强度有提高的倾向,使用含有固化剂的感光性树脂组合物时,机械强度可以更高。加热温度通常为180℃以上,优选200℃以上,通常250℃以下。
这样得到的滤色片,包含图案,上述滤色片可以与现有的滤色片一样通过组装到液晶显示装置上,可以得到适宜的液晶显示装置。
实施例
前面,对本发明实施方式进行了说明,但上述公开的本发明实施方式,只是例示,本发明范围并不限于这些实施方式。下面通过实施例更详细地说明本发明,但本发明并不限于这些实施例。
实施例1
[感光性树脂组合物的制备]
在溶剂中将6.507质量份(A)使甲苯二异氰酸酯(甲苯-2,4-二异氰酸酯和甲苯-2,6-二异氰酸酯的混合物),与己内酯和1-癸醇的反应物反应,使其与聚乙二醇反应,然后在与三级胺反应得到的产物中,进一步混合硬脂酸和BHT得到的组合物(商品名:Disperbyk-170,BYKChemie社制,30质量%溶液;溶剂乙酸甲氧基丙基酯/乙酸丁酯=6/1),
8.783质量份(B)甲基丙烯酸和甲基丙烯酸苄基酯的共聚物[甲基丙烯酸单位和甲基丙烯酸苄基酯单位的比为物质量比(摩尔比)27∶73,酸价为105,质量平均分子量为30,000],
10.735质量份(C)光聚合性化合物[二季戊四醇六丙烯酸酯],
0.390质量份(D)光聚合引发剂[2-甲基-2-吗啉-1-(4-甲基硫代苯基)丙烷-1-酮]
1.171质量份光聚合引发助剂(4,4’-双(二乙基氨基)二苯甲酮),
74.846质量份(E)溶剂[丙二醇单甲基醚乙酸酯]和
1.952质量份环氧化合物[邻甲酚酚醛型环氧树脂,商品名“スミェポキシESCN-195XL-80”(住友化学工业(株)制)]混合得到感光性树脂组合物。
[图案的形成]
在玻璃基板[コ-ニング社制,“#7059”](3)上,将上述得到的感光性树脂组合物用选装涂布法涂布后,在100℃干燥3分钟使挥发成分挥发,形成有色感光性树脂组合物层(4)(图2(a))。冷却后,在该有色感光性树脂组合物层(4)上插入光掩膜(5)并照射i线[波长365nm](6)曝光(图2(b))。作为i线光源,使用超高压水银灯,照射光量为150mJ/cm2。作为光掩膜,使用为形成线宽3μm,4μm,5μm,6μm,7μm,8μm,9μm,10μm,20μm,30μm,40μm,50μm和100μm的线状色像素的光掩膜。
然后将曝光后的玻璃基板[表面形成有色感光性树脂组合物层](3)浸渍在显像液[分别含有质量比0.05质量%氢氧化钠,0.2质量%丁基萘磺酸钠的水溶液]中显像,纯水洗涤。然后,在230℃加热20分钟,形成透明的图案(图2(c))。
[评价]
用反射型光学显微镜(观察倍率1,250倍)观察表面形态,未观察到表面粗糙,涂布缺陷和斑点,面内均匀性良好,析像度为6μm。
实施例2
[感光性树脂组合物的制备]
将3.387质量份(A)Disperbyk-170(BYKChemie社制,30质量%溶液;溶剂乙酸甲氧基丙基酯/乙酸丁酯=6/1),
9.140质量份(B)甲基丙烯酸和甲基丙烯酸苄基酯的共聚物[甲基丙烯酸单位和甲基丙烯酸苄基酯单位的比为物质量比(摩尔比)27∶73,酸价为105,质量平均分子量为30,000],
11.171质量份(C)光聚合性化合物[二季戊四醇六丙烯酸酯],
0.406质量份(D)光聚合引发剂[2-甲基-2-吗啉-1-(4-甲基硫代苯基)丙烷-1-酮]
1.219质量份光聚合引发助剂(4,4’-双(二乙基氨基)二苯甲酮),
74.846质量份(E)溶剂[丙二醇单甲基醚乙酸酯]和
2.031质量份环氧化合物[邻甲酚酚醛型环氧树脂,“酸味环氧树脂ESCN-195XL-80”(住友化学工业(株)制)]混合得到感光性树脂组合物。
[图案的形成]
用与实施例1所述相同的方法形成图案。
[评价]
用反射型光学显微镜(观察倍率1,250倍)观察图案形成的基板表面的形态,未观察到表面粗糙,涂布缺陷和斑点,面内均匀性良好,析像度为7μm。
实施例3
[感光性树脂组合物的制备]
将3.387质量份(A)Disperbyk-170(BYKChemie社制,30质量%溶液;溶剂乙酸甲氧基丙基酯/乙酸丁酯=6/1),
8.783质量份(B)甲基丙烯酸和甲基丙烯酸苄基酯的共聚物[甲基丙烯酸单位和甲基丙烯酸苄基酯单位的比为物质量比(摩尔比)27∶73,酸价为105,质量平均分子量为30,000],
10.735质量份(C)光聚合性化合物[二五赤藓醇六丙烯酸酯],
0.390质量份(D)光聚合引发剂[2-甲基-2-吗啉-1-(4-甲基硫代苯基)丙烷-1-酮]
1.171质量份光聚合引发助剂(2,4-二乙基噻吨酮),
74.846质量份(E)溶剂[丙二醇单甲基醚乙酸酯]和
1.952质量份环氧化合物[邻甲酚酚醛型环氧树脂,“酸味环氧树脂ESCN-195XL-80”(住友化学工业(株)制)]混合得到感光性树脂组合物。
[图案的形成]
用与实施例1所述相同的方法形成图案。
[评价]
用反射型光学显微镜(观察倍率1,250倍)观察图案形成的基板表面的形态,未观察到表面粗糙,涂布缺陷和斑点,面内均匀性良好,析像度为10μm。
实施例4
[感光性树脂组合物的制备]
将3.387质量份(A)Disperbyk-170(BYKChemie社制,30质量%溶液;溶剂乙酸甲氧基丙基酯/乙酸丁酯=6/1),
9.140质量份(B)甲基丙烯酸和甲基丙烯酸苄基酯的共聚物[甲基丙烯酸单位和甲基丙烯酸苄基酯单位的比为物质量比(摩尔比)27∶73,酸价为105,质量平均分子量为30,000],
11.171质量份(C)光聚合性化合物[二季戊四醇六丙烯酸酯],
0.406质量份(D)光聚合引发剂[2-甲基-2-吗啉-1-(4-甲基硫代苯基)丙烷-1-酮]
1.219质量份光聚合引发助剂(2,4-二乙基噻吨酮),
74.846质量份(E)溶剂[丙二醇单甲基醚乙酸酯]和
2.031质量份环氧化合物[邻甲酚酚醛型环氧树脂,“酸味环氧树脂ESCN-195XL-80”(住友化学工业(株)制)]混合得到感光性树脂组合物。
[图案的形成]
用与实施例1所述相同的方法形成图案。
[评价]
用反射型光学显微镜(观察倍率1,250倍)观察图案形成的基板表面的形态,未观察到表面粗糙,涂布缺陷和斑点,面内均匀性良好,析像度为10μm。
比较例1
[感光性树脂组合物的制备]
将9.527质量份(B)甲基丙烯酸和甲基丙烯酸苄基酯的共聚物[甲基丙烯酸单位和甲基丙烯酸苄基酯单位的比为物质量比(摩尔比)27∶73,酸价为105,质量平均分子量为30,000],
11.644质量份(C)光聚合性化合物[二五赤藓醇六丙烯酸酯],
0.423质量份(D)光聚合引发剂[2-甲基-2-吗啉-1-(4-甲基硫代苯基)丙烷-1-酮]
1.270质量份光聚合引发助剂[4,4’-双(二乙基氨基)二苯甲酮],
74.833质量份(E)溶剂[丙二醇单甲基醚乙酸酯]和
2.117质量份环氧化合物[邻甲酚酚醛型环氧树脂,“酸味环氧树脂ESCN-195XL-80”(住友化学工业(株)制)]混合得到感光性树脂组合物。
[图案的形成]
用与实施例1所述相同的方法形成图案。
[评价]
用反射型光学显微镜(观察倍率1,250倍)观察图案形成的基板表面的形态,观察到表面粗糙,涂布缺陷和斑点,析像度为10μm。
比较例2
[感光性树脂组合物的制备]
将9.527质量份(B)甲基丙烯酸和甲基丙烯酸苄基酯的共聚物[甲基丙烯酸单位和甲基丙烯酸苄基酯单位的比为物质量比(摩尔比)27∶73,酸价为105,质量平均分子量为30,000],
11.644质量份(C)光聚合性化合物[二五赤藓醇六丙烯酸酯],
0.423质量份(D)光聚合引发剂[2-甲基-2-吗啉-1-(4-甲基硫代苯基)丙烷-1-酮]
1.270质量份光聚合引发助剂[2,4-二乙基噻吨酮],
74.833质量份(E)溶剂[丙二醇单甲基醚乙酸酯]和
2.117质量份环氧化合物[邻甲酚酚醛型环氧树脂,“酸味环氧树脂ESCN-195XL-80”(住友化学工业(株)制)]混合得到感光性树脂组合物。
[图案的形成]
用与实施例1所述相同的方法形成图案。
[评价]
用反射型光学显微镜(观察倍率1,250倍)观察图案形成的基板表面的形态,观察到表面粗糙,涂布缺陷和斑点,析像度为10μm。
实施例5-11
[感光性树脂组合物的制备]
感光性树脂组合物的各成分比率按表1所示混合得到感光性树脂组合物。而且,各成分是与实施例1所用成分相同的成分。
[图案的形成]
用实施例1所述的方法形成图案。
[评价]
上述固化物层在400-780nm的透光率,用分光光度计(奥林巴斯光学工业(株)制OSP-SP200)测定。另外,透光率,将涂布前基板的透光率通过引入感光性树脂组合物层形成后基板的透光率校正,至于膜厚是在膜厚4μm得到的膜厚换算的,其平均值和分辨如表2所示。
比较例3
[感光性树脂组合物的制备]
不添加(A)反应混合物,感光性树脂组合物的各成分的比率按表1所示混合得到感光性树脂组合物。另外,各成分是与实施例1使用的成分相同的成分。
[图案的形成]
用与实施例1所述相同的方法形成图案。
[评价]
测定所得基板的400-780nm的平均透光率和析像度,结果示于表2。
表1
实施例5 | 实施例6 | 实施例7 | 实施例8 | 实施例9 | 实施例10 | 实施例11 | 比较例3 | |
ADispcrbyk-170(30质量%溶液) | 0.483 | 0.923 | 1.833 | 3.603 | 5.320 | 6.980 | 8.587 | 0.000 |
B粘合剂树脂 | 12.522 | 12.470 | 12.366 | 12.163 | 11.967 | 11.778 | 11.549 | 12.575 |
C光聚合性化合物 | 15.305 | 15.241 | 15.114 | 14.866 | 14.627 | 14.395 | 14.170 | 15.370 |
光聚合引发剂 | 0.557 | 0.554 | 0.550 | 0.541 | 0.532 | 0.523 | 0.515 | 0.559 |
光聚合引发助剂 | 1.670 | 1.663 | 1.649 | 1.622 | 1.596 | 1.570 | 1.546 | 1.677 |
E溶剂 | 67.000 | 67.00 | 67.000 | 67.000 | 67.000 | 67.000 | 67.000 | 67.000 |
环氧化合物 | 2.783 | 2.771 | 2.748 | 2.703 | 2.659 | 2.617 | 2.576 | 2.795 |
A*100/(B+C)固形成分换算值 | 0.499 | 0.999 | 2.001 | 3.999 | 8.001 | 8.001 | 9.999 | 0 |
表2
平均透光率(%) | 析像度(μm) | |
实施例5 | 94.8% | 8 |
实施例6 | 95.6% | 8 |
实施例7 | 97.9% | 7 |
实施例8 | 98.6% | 7 |
实施例9 | 98.7% | 6 |
实施例10 | 98.7% | 5 |
实施例11 | 98.7% | 4 |
比较例3 | 91.8% | 10 |
实施例12
[感光性树脂组合物的制备]
将13.17质量份(B)粘合剂树脂[甲基丙烯酸和甲基丙烯酸苄基酯的共聚物;甲基丙烯酸单位和甲基丙烯酸苄基酯单位的比为物质量比(摩尔比)27∶73,酸价为105,质量平均分子量为30,000],
16.10质量份(C)光聚合性化合物[二季戊四醇六丙烯酸酯],
0.59质量份(D)光聚合引发剂[2-甲基-2-吗啉-1-(4-甲基硫代苯基)丙烷-1-酮]
1.76质量份光聚合引发助剂[4,4’-双(二乙基氨基)二苯甲酮],
112.50质量份(E)溶剂[丙二醇单甲基醚乙酸酯]和
9.77质量份(A)BYK-170[BYKChemie社制,30质量%溶液;乙酸甲氧基丙基酯/乙酸丁酯=6/1]
2.93质量份环氧化合物[邻甲酚酚醛型环氧树脂,商品名“酸味环氧树脂ESCN-195XL-80”(住友化学工业(株)制)]混合得到混合物。在100质量份上述混合物中混合0.05质量份(F)1%聚醚变性硅油SH8400(东レ·ダゥコ-ニング·シリコ-ン(株)制)得到感光性树脂组合物。
[图案的形成]
在玻璃基板[300mm×300mm]上,将上述得到的有色感光性树脂组合物用旋转涂布法涂布后,在100℃干燥3分钟使挥发成分挥发,形成有色感光性树脂组合物层。所得图案没有斑点是良好的。
[评价]
该有色感光性树脂组合物层的膜厚从基板边缘部分向中心部分测定如表3所述,端部与中央部分膜厚相同,是良好的。
实施例13
除将实施例12的1%聚醚改性硅油SH8400(东レ·ダゥコ-ニング·シリコ-ン(株)制)的添加量变为0.20质量份外,与实施例1同样地形成图案。
[评价]
与实施例12同样地评价,得到的图案没有斑点是良好的,对于从基板边缘部分的平坦性如表3所示是良好的。
实施例14
除将实施例12的1%聚醚改性硅油SH8400(东レ·ダゥコ-ニンク·シリコ-ン(株)制)的添加量变为1.00质量份外,与实施例1同样地形成图案。
[评价]
与实施例12同样地评价,得到的图案没有斑点是良好的,对于从基板边缘部分的平坦性如表3所示是良好的。
实施例15
除将实施例12的添加量为0.02质量份的1%聚醚改性硅油SH8400(东レ·ダゥコ-ニング·シリコ-ン(株)制)变为1.00质量份1%聚醚变性硅油SH8400(东レ·ダゥコ-ニング·シリコ-ン(株)制),0.50质量份E5844(株)ダィキンフ ァィンケミカル研究所)外,与实施例1同样地形成图案。
[评价]
与实施例12同样地评价,得到的图案没有斑点是良好的,对于基板边缘部分的平坦性如表3所示,是良好的。
比较例4
除将实施例12的添加量为0.02质量份的1%聚醚改性硅油SH8400(东レ·ダゥコ-ニング·シリコ-ン(株)制)变为无添加外,与实施例1同样地形成图案。
[评价]
得到的层通过目视确认,得到的图案可见到条纹状的斑点。
表3
从基板边缘部分的距离(mm) | 膜厚(μm) | |||
实施例12 | 实施例13 | 实施例14 | 实施例15 | |
5 | 3.73 | 3.55 | 3.42 | 3.23 |
15 | 3.78 | 3.61 | 3.31 | 3.28 |
25 | 3.78 | 3.60 | 3.31 | 3.29 |
35 | 3.78 | 3.63 | 3.31 | 3.30 |
45 | 3.79 | 3.68 | 3.27 | 3.29 |
85 | 3.85 | 3.74 | 3.35 | 3.32 |
150 | 3.88 | 3.71 | 3.32 | 3.32 |
根据本发明的感光性树脂组合物,可以改良基板边缘部分的平坦性,可以形成不发生表面粗糙,涂布缺陷和斑点的图案,由于在400-780nm的透光率高因而透明性高,包含这些图案构成的滤色片具有良好的图像。
因此,本发明的感光性树脂组合物,作为滤色片用透明感光性树脂组合物有用,用它们形成的液晶显示装置也可以显示高品质的彩色图像。
Claims (12)
1.一种感光性树脂组合物,含有下列成分并且实质上不含有着色剂:
(A)使下述(a)~(d)化合物反应得到的反应产物,
(a)具有多个异氰酸酯基的化合物
(b)1价的醇
(c)具有2~3个选自-OH基、-NH2基和-NHR基,其中,R表示碳数1~4的烷基的化合物
(d)3级胺化合物;
(B)粘合剂聚合物;
(C)光聚合性化合物;
(D)光聚合性引发剂和
(E)溶剂,
其中相对于每100质量份(B)粘合剂聚合物和(C)光聚合性化合物的总量,含有0.5质量份以上50质量份以下(A)反应产物,0.1质量份以上20质量份以下(D)光聚合性引发剂,并且相对于感光性树脂组合物的固形成分,(B)粘合剂聚合物占质量比为5%以上90%以下,(C)光聚合性化合物占质量比为5%以上90%以下。
2.根据权利要求1所述的感光性树脂组合物,其中(A)(a)具有多个异氰酸酯基的化合物选自至少1种芳香族聚异氰酸酯,脂肪族聚异氰酸酯和脂环式聚异氰酸酯。
3.根据权利要求1或2所述的感光性树脂组合物,其中(A)(a)具有多个异氰酸酯基的化合物是使至少1种选自2,4-甲苯撑二异氰酸酯,2,5-甲苯撑二异氰酸酯,二苯基甲烷异氰酸酯,聚亚甲基聚苯基聚异氰酸酯,联间甲苯胺异氰酸酯,萘二异氰酸酯,六亚甲基二异氰酸酯,异佛尔酮二异氰酸酯,苯撑二甲基二异氰酸酯,氢化苯撑二甲基二异氰酸酯和二环己基甲烷二异氰酸酯反应得到的化合物。
4.根据权利要求1所述的感光性树脂组合物,其中(A)(a)具有多个异氰酸酯基的化合物,选自下述(a-1)~(a-8):
中至少一种化合物。
5.根据权利要求1所述的感光性树脂组合物,其中(A)(b)1价醇是Y-CH2OH所表示的化合物,
式中,Y表示选自下列基团:
(1)碳数7~30的脂肪族烃基;
(2)碳数6~30的脂环式烃基;
(3)脂肪族烃基中的至少1个亚甲基被-O-或-COO-基取代的取代脂肪族烃基;
(4)有脂肪族烃基的脂环式烃基的环上或脂肪族烃基上的亚甲基中的至少1个被-O-基或-COO-基取代的取代脂环式烃基,和
(5)具有至少1个脂肪族烃基的芳香族烃基的该脂肪族烃基上的至少1个亚甲基被-O-或-COO-取代的取代芳香族烃基。
6.根据权利要求1所述的感光性树脂组合物,其中(A)(c)化合物是
G-(E)n所表示的化合物
式中,G表示选自脂肪族烃基,脂环式烃基和芳香族烃基的基团;
上述G,各自独立地,在烃基内部至少有1个亚甲基被-O-基,-COO-基,-CONH-基,-S-基或-SO2-取代;
n表示2或3;
E表示选自-OH基,-NH2基和-NHR基,其中R定义与上述相同,E相互为相同或者不同。
7.根据权利要求1所述的感光性树脂组合物,其中(A)(d)三级胺化合物是Z-Q所表示的化合物
式中,Z表示含有为形成三级胺的基团的碳数2~10的脂肪族烃基,或者
至少含有1个氮原子的杂环式烃基,但是上述氮原子不与氢键合,
上述杂环式烃基有碳数1~10个的亚烷基插入并与Q基键合;
Q表示选自-OH基,-NH2基,-NHR,其中R定义与上述相同,和-SH基的基团。
8.根据权利要求1所述的感光性树脂组合物,其中还含有至少1种(F)选自聚硅氧烷系列表面活性剂,氟系列表面活性剂和具有氟原子的聚硅氧烷系列表面活性剂的表面活性剂。
9.根据权利要求8所述的感光性树脂组合物,其中(F)所示的表面活性剂的含量,相对于100质量份除(F)表面活性剂以外的感光性树脂组合物,为0.0001质量份以上0.6质量份以下。
10.一种图案形成方法,该方法是在基板上或基板上形成的固体有色感光性树脂组合物层上,涂布权利要求1~9中任意一项中所述的感光性树脂组合物,从涂布的感光性树脂组合物层除去挥发成分,介入光掩膜并将该除去挥发成分的层曝光,显像。
11.一种包含通过权利要求10所述的方法形成的图案的滤色片。
12.一种组装权利要求11所述的滤色片的液晶显示装置。
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