TWI621911B - 著色感光性樹脂組成物、彩色濾光片及彩色液晶顯示元件 - Google Patents
著色感光性樹脂組成物、彩色濾光片及彩色液晶顯示元件 Download PDFInfo
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- TWI621911B TWI621911B TW102145363A TW102145363A TWI621911B TW I621911 B TWI621911 B TW I621911B TW 102145363 A TW102145363 A TW 102145363A TW 102145363 A TW102145363 A TW 102145363A TW I621911 B TWI621911 B TW I621911B
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- 239000011342 resin composition Substances 0.000 title claims abstract description 52
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- 125000000962 organic group Chemical group 0.000 claims abstract description 62
- 150000001875 compounds Chemical class 0.000 claims abstract description 49
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 39
- 229920005989 resin Polymers 0.000 claims abstract description 35
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- 125000001424 substituent group Chemical group 0.000 claims description 54
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- 125000004122 cyclic group Chemical group 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
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- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 10
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- 125000003277 amino group Chemical group 0.000 claims description 5
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- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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Abstract
本發明之課題為提供一種色度特性、對比率、耐熱性、及對玻璃基板之密著性優異之著色感光性樹脂組成物、一種具備使用該著色感光性樹脂組成物所形成之著色層的彩色濾光片、及一種具備彩色濾光片之彩色液晶顯示元件。
本發明之解決手段為,本發明之著色感光性樹脂組成物含有鹼可溶性樹脂、光聚合性單體、光聚合起始劑、下述式(1)所表示之化合物、及有機顏料。式中,R1及R2分別獨立表示氫原子或有機基,但至少一者表示有機基。R1及R2可為該等鍵結形成環狀構造,亦可包含雜原子之鍵結。R3表示單鍵或有機基。R4~R9分別獨立表示氫原子、有機基等,R6及R7不成為羥基。R10表示氫原子或有機基。
Description
本發明係關於著色感光性樹脂組成物、彩色濾光片、及彩色液晶顯示元件。
使用於液晶面板或影像感測器等之彩色濾光片,一般由微影法所製造。此微影法中,首先於玻璃基板塗佈黑色之感光性樹脂組成物後、曝光、顯像、形成黑矩陣。其後,藉由重複將添加有綠、藍、紅各色之有機顏料的感光性樹脂組成物各自塗佈、曝光、顯像,形成各色之圖型於特定位置而製造彩色濾光片。
此時,若添加了有機顏料之感光性樹脂組成物的耐熱性低,於加熱步驟中產生異物於表面發生凹凸,對比變差,因此期望耐熱性高的組成物。例如,專利文獻1中,提案有使用具有特定環狀脒構造之化合物的著色組成物。此處所用之具有環狀脒構造之化合物,因為同時具有與著色劑親和性高的環狀脒部分,及與黏合劑成分親和性高的特性基,添加了此等之著色感光性樹脂組成物,分
散穩定性高、可減少聚合物分散劑等之分散劑的添加量,色相、對比率優異,且提升耐熱性之事被報告。
[專利文獻1]國際公開公報第2011/13318號
然而,上述添加了具有環狀脒構造之化合物的著色感光性樹脂組成物,有著對玻璃基板之密著性不足之問題。
本發明鑒於上述課題,以提供色度特性、對比率、耐熱性優異、提升對玻璃基板之密著性的著色感光性樹脂組成物、使用該著色感光性樹脂組成物所形成之彩色濾光片及具備彩色濾光片之彩色液晶顯示元件為目的。
本發明者們深入研究之結果,發現藉由含有特定之化合物而能解決上述課題,而完成本發明。
本發明之第一態樣為一種著色感光性樹脂組成物,其特徵為含有鹼可溶性樹脂、光聚合性單體、光聚合起始劑、下述式(1)所表示之化合物、及有機顏料。
(式中,R1及R2分別獨立表示氫原子或有機基。惟,R1及R2之至少一者表示有機基。R1及R2可為該等鍵結形成環狀構造,亦可包含雜原子之鍵結;R3表示單鍵或有機基。R4及R5分別獨立表示氫原子、鹵原子、羥基、巰基、硫醚基、硫基、矽醇基、硝基、亞硝基、亞磺酸基、磺酸基、磺酸鹽基、膦基、氧膦基、膦醯基、二負氧離子膦氧基、或有機基。R6、R7、R8、及R9分別獨立表示氫原子、鹵原子、羥基、巰基、硫醚基、硫基、矽醇基、硝基、亞硝基、亞磺酸基、磺酸基、磺酸鹽基、膦基、氧膦基、膦醯基、二負氧離子膦氧基、胺基、銨基、或有機基,惟,R6及R7不成為羥基。R6、R7、R8、及R9可為該等之2個以上鍵結形成環狀構造,亦可包含雜原子之鍵結。R10表示氫原子或有機基。)
本發明之第二態樣為一種彩色濾光片,其具備使用本發明之著色感光性樹脂組成物所形成之著色層,本發明之第三態樣為一種彩色液晶顯示元件,其具備本發明之彩色濾光片。
依據本發明,可得到具有優異色度、對比率,且耐熱性優異,對玻璃基板之密著性高的著色感光性樹脂組成物。因此,本發明之著色感光性樹脂組成物可適合使用於以彩色液晶顯示元件用彩色濾光片、固體攝像元件之色分解用彩色濾光片、有機EL顯示元件用彩色濾光片、電子紙用彩色濾光片為始之各種彩色濾光片的製作。
本發明之著色感光性樹脂組成物,含有鹼可溶性樹脂、光聚合性單體、光聚合起始劑、上述式(1)所表示之化合物、及有機顏料。首先,說明此等之構成成分。
作為本發明之鹼可溶性樹脂並無特別限定,可使用以往周知的鹼可溶性樹脂。此鹼可溶性樹脂可為具有乙烯性不飽和基者、亦可為不具乙烯性不飽和基者。
且,本說明書中之所謂的鹼可溶性樹脂,係指藉由樹脂濃度20質量%之樹脂溶液(溶劑:丙二醇單甲基醚乙酸酯),於玻璃基板上形成膜厚1μm之樹脂膜,浸漬於2.38質量%的氫氧化四甲銨(TMAH)水溶液中1分鐘時,膜厚溶解0.01μm以上者。
作為具有乙烯性不飽和基之鹼可溶性樹脂,例如,可使用藉由將環氧化合物與不飽和羧酸之反應物進而與多元酸酐反應所得之樹脂。
其中,以下述式(a-1)所表示之樹脂為佳。此式(a-1)所表示之樹脂,以該等自身光硬化性高之點來看為佳。
上述式(a-1)中,Xa表示下述式(a-2)所表示之基。
上述式(a-2)中,Ra1分別獨立表示氫原子、碳數1~6之烴基或鹵原子,Ra2分別獨立表示氫原子或甲基,Wa表示單鍵或下述式(a-3)所表示之基。
又,上述式(a-1)中,Ya表示去除來自二羧酸酐之酸酐基(-CO-O-CO-)之殘基。作為二羧酸酐之例,可舉例馬來酸酐、琥珀酸酐、伊康酸酐、酞酐、四氫酞酐、六氫酞酐、甲基內亞甲四氫酞酐、氯橋酸酐、甲基四氫酞酐、戊二酸酐等。
又,上述式(a-1)中,Za表示去除來自四羧酸二酐之2個酸酐基的殘基。作為四羧酸二酐之例,可舉例焦蜜石酸二酐、二苯甲酮四羧酸二酐、聯苯四羧酸二酐、聯苯醚四羧酸二酐等。
又,上述式(a-1)中,m表示0~20之整數。
又,作為具有乙烯性不飽和基之鹼可溶性樹脂,可使用於多元醇類與一元酸或多元酸縮合所得之聚酯預聚合物使(甲基)丙烯酸反應所得之聚酯(甲基)丙烯酸酯;使多元醇與具有2個異氰酸酯基之化合物反應後,與(甲基)丙烯酸反應所得之聚胺甲酸酯(甲基)丙烯酸酯;使雙酚A型環氧樹脂、雙酚F型環氧樹脂、雙酚S型環氧樹脂、酚或甲酚酚醛清漆型環氧樹脂、可溶酚醛型環氧樹脂、三酚甲烷型環氧樹脂、聚羧酸聚甘油酯、多元醇聚甘油酯、脂肪族或脂環式環氧樹脂、胺環氧樹脂、二羥苯型
環氧樹脂等之環氧樹脂,與(甲基)丙烯酸反應所得之環氧(甲基)丙烯酸酯樹脂等。
且,本說明書中,「(甲基)丙烯酸」係指丙烯酸及甲基丙烯酸兩者的意思。同樣的,「(甲基)丙烯酸酯」係指丙烯酸酯及甲基丙烯酸酯兩者的意思。
另一方面,作為不具乙烯性不飽和基之鹼可溶性樹脂,可使用至少使不具不飽和羧酸和脂環式基的含有環氧基之不飽和化合物與含有脂環式基之不飽和化合物共聚所得之樹脂。
作為不飽和羧酸,可舉例(甲基)丙烯酸、巴豆酸等之單羧酸;馬來酸、延胡索酸、檸康酸、中康酸、伊康酸等之二羧酸;此等二羧酸之酐;等。此等之中,由共聚反應性、所得樹脂之鹼溶解性、得到之容易性等點來看,(甲基)丙烯酸及馬來酸酐為佳。此等之不飽和羧酸,可單獨或組合2種以上來使用。
作為不具脂環式基的含有環氧基之不飽和化合物,可舉例環氧丙基(甲基)丙烯酸酯、2-甲基環氧丙基(甲基)丙烯酸酯、3,4-環氧丁基(甲基)丙烯酸酯、6,7-環氧庚基(甲基)丙烯酸酯、3,4-環氧環己基(甲基)丙烯酸酯等之(甲基)丙烯酸環氧烷基酯類;α-乙基丙烯酸環氧丙酯、α-n-丙基丙烯酸環氧丙酯、α-n-丁基丙烯酸環氧丙酯、α-乙基丙烯酸6,7-環氧庚酯等之α-烷基丙烯酸環氧烷基酯類;o-乙烯基苄基環氧丙基醚、m-乙烯基苄基環氧丙基醚、p-乙烯基苄基環氧丙基醚等之環氧丙基醚類;等。此等之
中,以共聚反應性、硬化後樹脂之強度等點來看,以環氧丙基(甲基)丙烯酸酯、2-甲基環氧丙基(甲基)丙烯酸酯、6,7-環氧庚基(甲基)丙烯酸酯、o-乙烯基苄基環氧丙基醚、m-乙烯基苄基環氧丙基醚、及p-乙烯基苄基環氧丙基醚為佳。此等之含有環氧基之不飽和化合物,可單獨或組合2種以上來使用。
作為含有脂環式基之不飽和化合物,只要是具有脂環式基之不飽和化合物並無特別限定。脂環式基可為單環亦可為多環。作為單環之脂環式基,可舉例環戊基、環己基等。又,作為多環之脂環式基,可舉例金剛烷基、降莰基、異莰基、三環壬基、三環癸基、四環十二基等。具體而言,作為含有脂環式基之不飽和化合物,例如可舉例下述式所表示之化合物。
上述式中,Ra3表示氫原子或甲基,Ra4表示單鍵或碳數1~6之2價的脂肪族飽和烴基,Ra5表示氫原子或碳數1~5之烷基。Ra4以單鍵、直鏈狀或支鏈狀之伸烷基,例如亞甲基、伸乙基、伸丙基、四亞甲基、乙基伸乙基、五亞甲基、六亞甲基為佳。Ra5,例如以甲基、乙基為佳。
此鹼可溶性樹脂中之來自上述不飽和羧酸的構成單位之比例,以3~25質量%為佳,5~25質量%更佳。又,來自上述含有環氧基之不飽和化合物的構成單位之比例,以71~95質量%為佳,75~90質量%更佳。又,來自上述含有脂環式基之不飽和化合物之構成單位的比例,以1~25質量%為佳,3~20質量%更佳,5~15質量%再更佳。藉由成為上述之範圍,能使所得樹脂之鹼溶解性成為適度的同時,提高著色感光性樹脂組成物之對玻璃基板的密著性、著色感光性樹脂組成物之硬化後的強度。
鹼可溶性樹脂之質量平均分子量,以1000~40000為佳,2000~30000更佳。藉由成為上述範圍,能在得到良好顯像性的同時,得到充分耐熱性、膜強度。
鹼可溶性樹脂之含量,相對於著色感光性樹脂組成物之固體成分而言以10~50質量%為佳,20~40質量%更佳。此處所謂之固體成分意指溶劑以外之成分。若鹼可溶性樹脂之含量太少,例如,會有鹼顯像性降低,所得著色感光性樹脂組成物之保存穩定性降低之虞,另一
方面若太多,相對地有機顏料濃度降低,故有難以達成以薄膜為目的之色濃度之虞。
本發明之著色感光性樹脂組成物,含有光聚合性單體。作為光聚合性單體,有單官能單體及多官能單體。
單官能單體,可舉例(甲基)丙烯醯胺、羥甲基(甲基)丙烯醯胺、甲氧基甲基(甲基)丙烯醯胺、乙氧基甲基(甲基)丙烯醯胺、丙氧基甲基(甲基)丙烯醯胺、丁氧基甲氧基甲基(甲基)丙烯醯胺、N-羥甲基(甲基)丙烯醯胺、N-羥基甲基(甲基)丙烯醯胺、(甲基)丙烯酸、延胡索酸、馬來酸、馬來酸酐、伊康酸、伊康酸酐、檸康酸、無水檸康酸、巴豆酸、2-丙烯醯胺-2-甲基丙烷磺酸、tert-丁基丙烯醯胺磺酸、甲基(甲基)丙烯酸酯、乙基(甲基)丙烯酸酯、丁基(甲基)丙烯酸酯、2-乙基己基(甲基)丙烯酸酯、環己基(甲基)丙烯酸酯、2-羥基乙基(甲基)丙烯酸酯、2-羥基丙基(甲基)丙烯酸酯、2-羥基丁基(甲基)丙烯酸酯、2-苯氧基-2-羥基丙基(甲基)丙烯酸酯、2-(甲基)丙烯醯氧基-2-羥基丙基酞酸酯、甘油單(甲基)丙烯酸酯、四氫呋喃(甲基)丙烯酸酯、二甲基胺基(甲基)丙烯酸酯、環氧丙基(甲基)丙烯酸酯、2,2,2-三氟乙基(甲基)丙烯酸酯、2,2,3,3-四氟丙基(甲基)丙烯酸酯、酞酸衍生物之半(甲基)丙烯酸酯等。此等之單官能單體,可單獨或組合2種以上來使用。
另一方面,作為多官能單體,可舉例乙二醇二(甲基)丙烯酸酯、二乙二醇二(甲基)丙烯酸酯、四乙二醇二(甲基)丙烯酸酯、丙二醇二(甲基)丙烯酸酯、聚丙二醇二(甲基)丙烯酸酯、丁二醇二(甲基)丙烯酸酯、新戊二醇二(甲基)丙烯酸酯、1,6-己二醇二(甲基)丙烯酸酯、三羥甲基丙烷三(甲基)丙烯酸酯、甘油二(甲基)丙烯酸酯、新戊四醇三丙烯酸酯、新戊四醇四丙烯酸酯、二新戊四醇五丙烯酸酯、二新戊四醇六丙烯酸酯、新戊四醇二(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、二新戊四醇五(甲基)丙烯酸酯、二新戊四醇六(甲基)丙烯酸酯、2,2-雙(4-(甲基)丙烯醯氧基二乙氧基苯基)丙烷、2,2-雙(4-(甲基)丙烯醯氧基聚乙氧基苯基)丙烷、2-羥基-3-(甲基)丙烯醯氧基丙基(甲基)丙烯酸酯、乙二醇二環氧丙基醚二(甲基)丙烯酸酯、二乙二醇二環氧丙基醚二(甲基)丙烯酸酯、酞酸二環氧丙基酯二(甲基)丙烯酸酯、甘油三丙烯酸酯、甘油聚環氧丙基醚聚(甲基)丙烯酸酯、胺甲酸乙酯(甲基)丙烯酸酯(亦即,甲伸苯基二異氰酸酯)、三甲基六亞甲基二異氰酸酯與六亞甲基二異氰酸酯與2-羥基乙基(甲基)丙烯酸酯之反應物、亞甲基雙(甲基)丙烯醯胺、(甲基)丙烯醯胺亞甲基醚、多元醇與N-羥甲基(甲基)丙烯醯胺之縮合物等的多官能單體,或三丙烯醯基六氫嗪等。此等多官能單體,可單獨或組合2種以上來使用。
本發明中之光聚合性單體的含量,相對於著
色感光性樹脂組成物之固體成分而言以10~50質量%為佳、20~40質量%更佳。此情形,若光聚合性單體之含量太少,有無法得到充分硬化性之虞,若含量太多,有鹼顯像性降低,未曝光部分之玻璃基板上或遮光層上易產生浮渣、殘膜等的傾向。
本發明之著色感光性樹脂組成物,含有光聚合起始劑。藉此可賦予敏幅射線性。此處所謂之輻射線,係包含可見光線、紫外線、遠紫外線、電子線、X光線等的概念。
用於本發明之光聚合起始劑,係可藉由可見光線、紫外線、遠紫外線、電子線、X光線之輻射線的曝光,開始光聚合性單體的聚合產生活性種的化合物。
作為如此之光聚合起始劑,例如可舉例塞噸酮系化合物、苯乙酮系化合物、聯咪唑化合物、三嗪系化合物、O-醯基肟系化合物、鎓鹽系化合物、安息香化合物、二苯甲酮系化合物、α-二酮化合物、多核醌系化合物、重氮系化合物、亞胺磺酸鹽化合物等。
本發明之中,作為較佳之光聚合起始劑,可舉例下述式(2)所表示之肟酯化合物。
(式中、Rb1及Rb2為由1價之有機基、胺基、鹵素、硝基、及氰基所成群中所選之基,Rb3為氫原子、或碳數1~6之烷基,A為S或O,n為0~4之整數,p為0或1,q為0~4之整數。)
上述式(2)中,Rb1為1價之有機基時,Rb1於不妨礙本發明目的之範圍內並無特別限定,適宜地選擇各種有機基。Rb1為有機基時的合適例子可舉例烷基、烷氧基、環烷基、環烷氧基、飽和脂肪族醯基、烷氧基羰基、飽和脂肪族醯氧基、可具有取代基之苯基、可具有取代基之苯氧基、可具有取代基之苯甲醯基、可具有取代基之苯氧基羰基、可具有取代基之苯甲醯基氧基、可具有取代基之苯基烷基、可具有取代基之萘基、可具有取代基之萘氧基、可具有取代基之萘甲醯基、可具有取代基之萘氧基羰基、可具有取代基之萘甲醯氧基、可具有取代基之萘基烷基、可具有取代基之雜環基、經1或2之有機基取代之胺基、嗎啉-1-基、及哌嗪-1-基等。N為2~4之整數時,Rb1可相同或相異。又,取代基之碳數中,不包含取代基
所進一步具有之取代基的碳數。
Rb1為烷基時,其碳數以1~20為佳,1~6更佳。又,Rb1為烷基時,可為直鏈,亦可為支鏈。又,Rb1為烷基時,烷基於碳鏈中可包含醚鍵(-O-)。
Rb1為烷氧基時,其碳數以1~20為佳,1~6更佳。又,Rb1為烷氧基時,可為直鏈,亦可為支鏈。又,Rb1為烷氧基時,烷氧基於碳鏈中可包含醚鍵(-O-)。
Rb1為環烷基、或環烷氧基時,其碳數以3~10為佳,3~6更佳。
Rb1為飽和脂肪族醯基、或飽和脂肪族醯氧基時,其碳數以2~20為佳,2~7更佳。
Rb1為烷氧基羰基時、其碳數以2~20為佳,2~7更佳。
Rb1為苯基烷基時,其碳數以7~20為佳,7~10更佳。又Rb1為萘基烷基時,其碳數以11~20為佳,11~14更佳。Rb1為苯基烷基或萘基烷基時,Rb1為苯基或萘基上進一步具有取代基亦可。
Rb1為雜環基時,雜環基為1以上之包含N、S、O之5員或6員的單環,或是該單環彼此、或該單環與苯環縮合之雜環基。雜環基為縮合環時,環數為3為止。Rb1為雜環基時,雜環基進一步具有取代基亦可。
Rb1為經1或2之有機基取代之胺基時,有機基之合適的例可舉例碳數1~20之烷基、碳數3~10之環烷基、碳數2~20之飽和脂肪族醯基、可具有取代基之苯
基、可具有取代基之苯甲醯基、可具有取代基之碳數7~20之苯基烷基、可具有取代基之萘基、可具有取代基之萘甲醯基、可具有取代基之碳數11~20之萘基烷基、及雜環基等。此等合適之有機基的具體例與Rb1相同。
作為包含於Rb1之苯基、萘基、及雜環基進一步具有取代基時的取代基,可舉例碳數1~6之烷基、碳數1~6之烷氧基、碳數2~7之飽和脂肪族醯基、碳數2~7之烷氧基羰基、碳數2~7之飽和脂肪族醯氧基、具有碳數1~6之烷基的單烷基胺基、具有碳數1~6之烷基的二烷基胺基、嗎啉-1-基、哌嗪-1-基、鹵素、硝基、及氰基等。包含於R1之苯基、萘基、及雜環基進一步具有取代基時,其取代基的數,雖在不阻礙本發明目的之範圍內並無限定,但以1~4為佳。包含於R1之苯基、萘基、及雜環基,具有複數之取代基時,複數之取代基可為相同亦可相異。
Rb1與苯基鍵結的位置,關於Rb1鍵結之苯基,當苯基與肟酯化合物之主骨架的鍵的位置為1位、甲基之位置為2位時,以4位、或5位為佳,5位更佳。又,n為0~3之整數為佳,0~2之整數更佳,0、或1特佳。
式(2)中之Rb2為有機基時,不阻礙本發明目的之範圍內,可選擇各種之有機基。作為式(2)中之Rb2為有機基時之合適的例,可舉例碳數1~6之烷基;碳數1~6之烷氧基;碳數2~7之飽和脂肪族醯基;碳數2~7
之烷氧基羰基;碳數2~7之飽和脂肪族醯氧基;苯基;萘基;苯甲醯基;萘甲醯基;經碳數1~6之烷基、嗎啉-1-基、哌嗪-1-基、及苯基所成群中所選擇之基取代的苯甲醯基;具有碳數1~6之烷基的單烷基胺基;具有碳數1~6之烷基的二烷基胺基;嗎啉-1-基;哌嗪-1-基;鹵素;硝基;氰基。
Rb2之中,以苯甲醯基;萘甲醯基;經碳數1~6之烷基、嗎啉-1-基、哌嗪-1-基、及苯基所成群中所選擇之基取代的苯甲醯基;硝基為佳,苯甲醯基;萘甲醯基;2-甲基苯基羰基;4-(哌嗪-1-基)苯基羰基;4-(苯基)苯基羰基更佳。
又,式(2)之中,q為0~3之整數為佳,0~2之整數更佳,0、或1特佳。q為1時,Rb2之鍵結位置,相對於Rb2鍵結之苯基與硫原子鍵結的鍵,以對位為佳。
作為包含於Rb2之苯基、萘基、及雜環基進一步具有取代基時的取代基,可舉例碳數1~6之烷基、碳數1~6之烷氧基、碳數2~7之飽和脂肪族醯基、碳數2~7之烷氧基羰基、碳數2~7之飽和脂肪族醯氧基、具有碳數1~6之烷基的單烷基胺基、具有碳數1~6之烷基的二烷基胺基、嗎啉-1-基、哌嗪-1-基、鹵素、硝基、及氰基等。包含於Rb2之苯基、萘基、及雜環基進一步具有取代基時,其取代基之數,雖在不阻礙本發明目的之範圍內並無限定,以1~4為佳。包含於Rb2之苯基、萘基、及雜環基,具有複數之取代基時,複數之取代基,可為相
同亦可相異。
式(2)中之Rb3為氫原子、或碳數1~6之烷基。Rb3為甲基時、式(2)所表示之化合物所成之光聚合起始劑特別感度優異。
作為式(2)所表示之肟酯化合物中特別合適的化合物,可舉例下述式之化合物。
作為用於本發明之光聚合起始劑,上述之肟酯化合物以外,可舉例1-羥基環己基苯基酮、2-羥基-2-甲基-1-苯基丙烷-1-酮、1-〔4-(2-羥基乙氧基)苯基〕-2-羥基-2-甲基-1-丙烷-1-酮、1-(4-異丙基苯基)-2-羥基-2-甲基丙烷-1-酮、1-(4-十二基苯基)-2-羥基-2-甲基丙烷-1-酮、2,2-二甲氧基-1,2-二苯基乙烷-1-酮、雙(4-二甲基胺基苯基)酮、2-甲基-1-〔4-(甲基硫)苯基〕-2-嗎啉代丙烷-1-
酮、2-苄基-2-二甲基胺基-1-(4-嗎啉代苯基)-丁烷-1-酮、乙酮,1-〔9-乙基-6-(2-甲基苯甲醯基)-9H-咔唑基-3-基〕,1-(o-乙醯基肟)、2,4,6-三甲基苯甲醯基二苯基膦氧化物、4-苯甲醯基-4’-甲基二甲基硫化物、4-二甲基胺基安息香酸、4-二甲基胺基安息香酸甲酯、4-二甲基胺基安息香酸乙酯、4-二甲基胺基安息香酸丁酯、4-二甲基胺基-2-乙基己基安息香酸、4-二甲基胺基-2-異戊基安息香酸、苄基-β-甲氧基乙基縮醛、苄基二甲基縮酮、1-苯基-1,2-丙烷二酮-2-(o-乙氧基羰基)肟、o-苯甲醯基安息香酸甲基、2,4-二乙基塞噸酮、2-氯塞噸酮、2,4-二甲基塞噸酮、1-氯-4-丙氧基塞噸酮、噻噸、2-氯噻噸、2,4-二乙基噻噸、2-甲基噻噸、2-異丙基噻噸、2-乙基蒽醌、八甲基蒽醌、1,2-苯并蒽醌、2,3-二苯基蒽醌、偶氮雙異丁腈、苯甲醯基過氧化氫、異丙苯過氧化氫、2-巰基苯并咪唑、2-巰基苯并噁唑、2-巰基苯并噻唑、2-(o-氯苯基)-4,5-二苯基咪唑二聚物、2-(o-氯苯基)-4,5-二(甲氧基苯基)咪唑二聚物、2-(o-氟苯基)-4,5-二苯基咪唑二聚物、2-(o-甲氧基苯基)-4,5-二苯基咪唑二聚物、2-(p-甲氧基苯基)-4,5-二苯基咪唑二聚物、2,4,5-三芳基咪唑二聚物、二苯甲酮、2-氯二苯甲酮、4,4’-雙二甲基胺基二苯甲酮(即,米其勒酮)、4,4’-雙二乙基胺基二苯甲酮(即,乙基米其勒酮)、4,4’-二氯二苯甲酮、3,3-二甲基-4-甲氧基二苯甲酮、苄基、安息香、安息香甲基醚、安息香乙基醚、安息香異丙基醚、安息香-n-丁基醚、安息香異丁基醚、安息香丁基醚、苯乙
酮、2,2-二乙氧基苯乙酮、p-二甲基苯乙酮、p-二甲基胺基丙醯苯、二氯苯乙酮、三氯苯乙酮、p-tert-丁基苯乙酮、p-二甲基胺基苯乙酮、p-tert-丁基三氯苯乙酮、p-tert-丁基二氯苯乙酮、α,α-二氯-4-苯氧基苯乙酮、塞噸酮、2-甲基塞噸酮、2-異丙基塞噸酮、二苯并環庚酮、戊基-4-二甲基胺基苯甲酸酯、9-苯基吖啶、1,7-雙-(9-吖啶基)庚烷、1,5-雙-(9-吖啶基)戊烷、1,3-雙-(9-吖啶基)丙烷、p-甲氧基三嗪、2,4,6-參(三氯甲基)-s-三嗪、2-甲基-4,6-雙(三氯甲基)-s-三嗪、2-〔2-(5-甲基呋喃-2-基)乙烯基〕-4,6-雙(三氯甲基)-s-三嗪、2-〔2-(呋喃-2-基)乙烯基〕-4,6-雙(三氯甲基)-s-三嗪、2-〔2-(4-二乙基胺基-2-甲基苯基)乙烯基〕-4,6-雙(三氯甲基)-s-三嗪、2-〔2-(3,4-二甲氧基苯基)乙烯基〕-4,6-雙(三氯甲基)-s-三嗪、2-(4-甲氧基苯基)-4,6-雙(三氯甲基)-s-三嗪、2-(4-乙氧基苯乙烯基)-4,6-雙(三氯甲基)-s-三嗪、2-(4-n-丁氧基苯基)-4,6-雙(三氯甲基)-s-三嗪、2,4-雙-三氯甲基-6-(3-溴-4-甲氧基)苯基-s-三嗪、2,4-雙-三氯甲基-6-(2-溴-4-甲氧基)苯基-s-三嗪、2,4-雙-三氯甲基-6-(3-溴-4-甲氧基)苯乙烯基苯基-s-三嗪、2,4-雙-三氯甲基-6-(2-溴-4-甲氧基)苯乙烯基苯基-s-三嗪等。此等之光聚合起始劑可單獨或混合2種以上使用。
本發明中,光聚合起始劑之含量,相對於著色感光性樹脂組成物之固體成分以1~20質量%為佳,1~10質量%更佳。此情形,光聚合起始劑之含量若太少,
有曝光造成之硬化不充分之虞,另一方面若太多,有形成之著色層於顯像時易從玻璃基板剝離的傾向。
本發明之著色感光性樹脂組成物,含有下述式(1)所表示之化合物。此化合物對有機溶劑之溶解性良好,又,藉由輻射線照射或加熱產生鹼,能提升色相、對比率、耐熱性、對玻璃基板之密著性。
上述式(1)中,R1及R2分別獨立表示氫原子或有機基,但R1及R2至少一方表示有機基。
作為R1及R2中之有機基,可舉例烷基、烯基、環烷基、環烯基、芳基、芳烷基等。此有機基,該有機基中包含雜原子等之烴基以外的鍵結或取代基亦可。又,此有機基為直鏈狀、支鏈狀、環狀之任一種皆可。此有機基,通常為1價,但形成環狀構造之情形等,可為2價以上之有機基。
R1及R2,可為該等鍵結形成環狀構造,亦可
為進一步包含雜原子之鍵結。作為環狀構造,可舉例雜環烷基、雜芳基等,亦可為縮合環。
作為R1及R2之有機基中之烴基以外的鍵結,在不損及本發明效果範圍內則無特別限定,可舉例包含氧原子、氮原子、矽原子等之雜原子的鍵結。作為具體例,可舉例醚鍵結、硫醚鍵結、羰基鍵結、硫羰基鍵結、酯鍵結、醯胺鍵結、胺甲酸乙酯鍵結、亞胺鍵結(-N=C(-R)-、-C(=NR)-:R表示氫原子或有機基)、碳酸酯鍵結、磺醯基鍵結、亞磺醯基鍵結、偶氮鍵結等。
由耐熱性之觀點來看,作為R1及R2之有機基中之烴基以外的鍵結,乙醚鍵結、硫醚鍵結、羰基鍵結、硫羰基鍵結、酯鍵結、醯胺鍵結、胺甲酸乙酯鍵結、亞胺鍵結(-N=C(-R)-、-C(=NR)-:R表示氫原子或1價之有機基)、碳酸酯鍵結、磺醯基鍵結、亞磺醯基鍵結為佳。
作為R1及R2之有機基中之烴基以外的取代基,在不損及本發明效果範圍內則無特別限定,可舉例鹵原子、羥基、巰基、硫醚基、氰基、異氰基、氰氧基、異氰氧基、硫氰氧基、異硫氰氧基、硫基、矽醇基、烷氧基、烷氧基羰基、胺甲醯基、硫胺甲醯基、硝基、亞硝基、羧基、羧酸酯基、醯基、醯氧基、亞磺酸基、磺酸基、磺酸鹽基、膦基、氧膦基、膦醯基、二負氧離子膦氧基、羥基亞胺基、烷基醚基、烯基醚基、烷基硫醚基、烯基硫醚基、芳基醚基、芳基硫醚基、胺基(-NH2、-NHR、-NRR’:R及R’分別獨立表示烴基)等。包含於上述取代基
之氫原子,經烴基取代亦可。又,包含於上述取代基之烴基,為直鏈狀、支鏈狀、及環狀之任一種皆可。
作為R1及R2之有機基中之烴基以外的取代基,以鹵原子、羥基、巰基、硫醚基、氰基、異氰基、氰氧基、異氰氧基、硫氰氧基、異硫氰氧基、硫基、矽醇基、烷氧基、烷氧基羰基、胺甲醯基、硫胺甲醯基、硝基、亞硝基、羧基、羧酸酯基、醯基、醯氧基、亞磺酸基、磺酸基、磺酸鹽基、膦基、氧膦基、膦醯基、二負氧離子膦氧基、羥基亞胺基、烷基醚基、烯基醚基、烷基硫醚基、烯基硫醚基、芳基醚基、芳基硫醚基為佳。
以上之中,R1及R2至少一者為碳數1~12之烷基或碳數1~12之芳基,或者是互相鍵結形成碳數2~20之雜環烷基或雜芳基者為佳。雜環烷基可舉例n-六氫吡啶基、n-嗎啉基等,雜芳基可舉例咪唑基、吡唑基等。
上述式(1)中,R3表示單鍵或有機基。
作為R3中之有機基,可舉例由烷基、烯基、環烷基、環烯基、芳基、芳烷基等去除1個氫原子之基。此有機基,於該有機基中包含取代基亦可。作為取代基,可舉例R1及R2中所例示者。又,此有機基,可為直鏈狀、支鏈狀之任一者皆可。
以上之中,作為R3,以由單鍵、或碳數1~12之烷基或碳數1~12之芳基中去除1個氫原子之基為佳。
上述式(1)中,R4及R5分別獨立表示氫原子、
鹵原子、羥基、巰基、硫醚基、硫基、矽醇基、硝基、亞硝基、亞磺酸基、磺酸基、磺酸鹽基、膦基、氧膦基、膦醯基、二負氧離子膦氧基、或有機基。
作為R4及R5中之有機基,可舉例R1及R2中之例示者。此有機基,與R1及R2之情形相同,於該有機基中包含雜原子等之烴基以外的鍵結或取代基亦可。又,此有機基,為直鏈狀、支鏈狀、環狀之任一者皆可。
以上之中,作為R4及R5,分別獨立為氫原子、碳數1~10之烷基、碳數4~13之環烷基、碳數4~13之環烯基、碳數7~16之芳基氧基烷基、碳數7~20之芳烷基、具有氰基之碳數2~11之烷基、具有羥基之碳數1~10之烷基、碳數1~10之烷氧基、碳數2~11之醯胺基、碳數1~10之烷基硫基、碳數1~10之醯基、碳數2~11之酯基(-COOR、-OCOR:R表示烴基)、碳數6~20之芳基、經推電子基及/或拉電子基團取代之碳數6~20之芳基、經推電子基團及/或拉電子基團取代之苄基、氰基、甲基硫基為佳。更佳為,R4及R5兩者為氫原子,或R4為甲基、R5為氫原子。
上述式(1)中、R6、R7、R8、及R9分別獨立表示氫原子、鹵原子、羥基、巰基、硫醚基、硫基、矽醇基、硝基、亞硝基、亞磺酸基、磺酸基、磺酸鹽基、膦基、氧膦基、膦醯基、二負氧離子膦氧基、胺基、銨基、或有機基。
作為R6、R7、R8、及R9中之有機基,可舉例R1及
R2中之例示者。此有機基,與R1及R2之情形相同,於該有機基中包含雜原子等之烴基以外的鍵結或取代基亦可。又,此有機基,為直鏈狀、支鏈狀、環狀之任一者皆可。
且,上述式(1)中,R6及R7不為羥基。
R6、R7、R8、及R9,可為該等之2個以上鍵結形成環狀構造,亦可為包含雜原子之鍵結。作為環狀構造,可舉例雜環烷基、雜芳基等,亦可為縮合環。例如,R6、R7、R8、及R9,該等之2個以上鍵結,R6、R7、R8、及R9共有所鍵結的苯環之原子形成萘、蒽、菲、茚等之縮合環。
以上之中,作為R6、R7、R8、及R9,以分別獨立為氫原子、碳數1~10之烷基、碳數4~13之環烷基、碳數4~13之環烯基、碳數7~16之芳基氧基烷基、碳數7~20之芳烷基、具有氰基之碳數2~11之烷基、具有羥基之碳數1~10之烷基、碳數1~10之烷氧基、碳數2~11之醯胺基、碳數1~10之烷基硫基、碳數1~10之醯基、碳數2~11之酯基、碳數6~20之芳基、經推電子基團及/或拉電子基團取代之碳數6~20之芳基、經推電子基團及/或拉電子基團取代之苄基、氰基、甲基硫基、硝基為佳。
又,作為R6、R7、R8、及R9,該等之2個以上鍵結、R6、R7、R8、及R9共有所鍵結的苯環之原子形成萘、蒽、菲、茚等之縮合環的情形,以吸收波長為長波長化之點來看為佳。
更佳為,R6、R7、R8、及R9之全部為氫原子,或R6、R7、R8、及R9之任一者為硝基,其餘3個為氫原子。
上述式(1)中,R10表示氫原子或有機基。
作為R10中之有機基,可舉例R1及R2中之例示者。此有機基,與R1及R2之情形相同,於該有機基中包含雜原子等之烴基以外的鍵結或取代基亦可。又,此有機基,為直鏈狀、支鏈狀、環狀之任一者皆可。
上述式(1)所表示之化合物,因為於苯環之對位具有-OR10基,對溶劑之溶解性良好。
以上之中,作為R10,以氫原子、或碳數1~12之烷基為佳,甲基更佳。
上述式(1)所表示之化合物之中,作為特別佳之具體例,可舉例下述式所表示之化合物。
本發明中,上述式(1)所表示之化合物可單獨或混合2種以上使用。
又,上述式(1)所表示之化合物之含量,相對於上述光聚合起始劑100質量份而言以1~100質量份為佳,5~50質量份更佳。在如此之範圍,藉由使用上述式(1)所表示之化合物,可得到對比率、耐熱性優異、對玻璃基板之密著性高的著色感光性樹脂組成物。
本發明之著色感光性樹脂組成物,含有有機顏料。有機顏料雖無特別限定,但例如,比色指數(C.I.;The
Society of Dyers and Colourists公司發行)中色素(Pigment)分類之化合物,具體而言,使用如下述之編有比色指數(C.I.)號碼者為佳。
C.I.色素黃1(以下,與「C.I.色素黃」相同,僅記載號碼。)、3、11、12、13、14、15、16、17、20、24、31、53、55、60、61、65、71、73、74、81、83、86、93、95、97、98、99、100、101、104、106、108、109、110、113、114、116、117、119、120、125、126、127、128、129、137、138、139、147、148、150、151、152、153、154、155、156、166、167、168、175、180、185;C.I.色素橘1(以下,與「C.I.色素橘」相同,僅記載號碼。)、5、13、14、16、17、24、34、36、38、40、43、46、49、51、55、59、61、63、64、71、73;C.I.色素紫1(以下,與「C.I.色素紫」相同,僅記載號碼。)、19、23、29、30、32、36、37、38、39、40、50;C.I.色素紅1(以下,與「C.I.色素紅」相同,僅記載號碼。)、2、3、4、5、6、7、8、9、10、11、12、14、15、16、17、18、19、21、22、23、30、31、32、37、38、40、41、42、48:1、48:2、48:3、48:4、49:1、49:2、50:1、52:1、53:1、57、57:1、57:2、58:2、58:4、60:1、63:1、63:2、64:1、81:1、83、88、90:1、97、101、102、104、105、106、108、
112、113、114、122、123、144、146、149、150、151、155、166、168、170、171、172、174、175、176、177、178、179、180、185、187、188、190、192、193、194、202、206、207、208、209、215、216、217、220、223、224、226、227、228、240、242、243、245、254、255、264、265;C.I.色素藍1(以下,與「C.I.色素藍」相同,僅記載號碼。)、2、15、15:3、15:4、15:6、16、22、60、64、66;C.I.色素綠7、C.I.色素綠36、C.I.色素綠37、色素綠58;C.I.色素棕23、C.I.色素棕25、C.I.色素棕26、C.I.色素棕28;C.I.色素黑1、C.I.色素黑7。
本發明中,可將有機顏料藉由再結晶法、再沈澱法、溶劑洗淨法、昇華法、真空過熱法或此等之組合純化使用。
有機顏料之含量,由形成透明性及色純度優異之像素的點來看,相對於著色感光性樹脂組成物之固體成分而言以10~200質量%為佳,50~150質量%更佳。
且,有機顏料,以使用分散劑以適當的濃度分散成為分散液後,添加至著色感光性樹脂組成物為佳。作為周知的分散劑,以聚合物分散劑為佳,例如,丙烯酸系共聚體分散劑、聚胺甲酸酯系分散劑、聚酯系分散劑、
聚乙烯亞胺系分散劑、聚烯丙基胺系分散劑等。其中以聚胺甲酸酯系分散劑為佳。若使用此等聚合物分散劑,可改善有機顏料之分散性及分散穩定性、提升色相、對比率、耐熱性。
本發明之著色感光性樹脂組成物,可含有溶劑。作為用於本發明之溶劑,只要是分散或溶解上述式(1)所表示之化合物及有機顏料、或後述之其他成分,且不與此等成分反應,具有適度之揮發性者即可。
作為如此之溶劑,可舉例例如,乙二醇單甲基醚、乙二醇單乙基醚、乙二醇-n-丙基醚、乙二醇單-n-丁基醚、二乙二醇單甲基醚、二乙二醇單乙基醚、二乙二醇單-n-丙基醚、二乙二醇單-n-丁基醚、三乙二醇單甲基醚、三乙二醇單乙基醚、丙二醇單甲基醚、丙二醇單乙基醚、丙二醇單-n-丙基醚、丙二醇單-n-丁基醚、二丙二醇單甲基醚、二丙二醇單乙基醚、二丙二醇單-n-丙基醚、二丙二醇單-n-丁基醚、三丙二醇單甲基醚、三丙二醇單乙基醚等之(聚)烷二醇單烷基醚類;乙二醇單甲基醚乙酸酯、乙二醇單乙基醚乙酸酯、二乙二醇單甲基醚乙酸酯、二乙二醇單乙基醚乙酸酯、丙二醇單甲基醚乙酸酯、丙二醇單乙基醚乙酸酯等之(聚)烷二醇單烷基醚乙酸酯類;二乙二醇二甲基醚、二乙二醇甲基乙基醚、二乙二醇二乙基醚、四氫呋喃等之其他醚類;甲基乙基酮、環己酮、2-庚
酮、3-庚酮等之酮類;2-羥基丙酸甲酯、2-羥基丙酸乙酯等之乳酸烷基酯類;2-羥基-2-甲基丙酸乙酯、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、乙氧基乙酸乙酯、羥基乙酸乙酯、2-羥基-3-甲基丁烷酸甲酯、3-甲基-3-甲氧基丁基乙酸酯、3-甲基-3-甲氧基丁基丙酸酯、乙酸乙酯、乙酸n-丙酯、乙酸異丙酯、乙酸n-丁酯、乙酸異丁酯、蟻酸n-戊酯、乙酸異戊酯、丙酸n-丁酯、酪酸乙酯、酪酸n-丙酯、酪酸異丙酯、酪酸n-丁酯、丙酮酸甲酯、丙酮酸乙酯、丙酮酸n-丙酯、乙醯乙酸甲酯、乙醯乙酸乙酯、2-側氧基丁烷酸乙酯等之其他酯類;甲苯、二甲苯等之芳香族烴類;N-甲基吡咯烷酮、N,N-二甲基甲醯胺、N,N-二甲基乙醯胺等之醯胺類等。此等之溶劑,可單獨或組合2種以上來使用。
上述溶劑之中,因為丙二醇單甲基醚、乙二醇單甲基醚乙酸酯、丙二醇單甲基醚乙酸酯、丙二醇單乙基醚乙酸酯、二乙二醇二甲基醚、二乙二醇甲基乙基醚、環己酮、3-甲氧基丁基乙酸酯,對於上述式(1)所表示之化合物顯示優異之溶解性的同時,對上述有機顏料之分散性能夠良好故為佳,使用丙二醇單甲基醚乙酸酯、3-甲氧基丁基乙酸酯特佳。
溶劑之含量,由所得之著色感光性樹脂組成物之塗佈性、穩定性等之觀點來看,著色感光性樹脂組成物之全固體成分之合計濃度,以成為5~30質量%之量為佳,成為10~20質量%之量更佳。
本發明之著色感光性樹脂組成物,應需要可含有各種添加劑。
作為添加劑,可舉例例如,玻璃、氧化鋁等之填充劑;聚乙烯基醇、聚(氟烷基丙烯酸酯)類等之高分子化合物;氟系界面活性劑、矽系界面活性劑等之界面活性劑;乙烯基三甲氧基矽烷、乙烯基三乙氧基矽烷、乙烯基參(2-甲氧基乙氧基)矽烷、N-(2-胺基乙基)-3-胺基丙基甲基二甲氧基矽烷、N-(2-胺基乙基)-3-胺基丙基三甲氧基矽烷、3-胺基丙基三乙氧基矽烷、3-環氧丙氧基丙基三甲氧基矽烷、3-環氧丙氧基丙基甲基二甲氧基矽烷、2-(3,4-環氧環己基)乙基三甲氧基矽烷、3-氯丙基甲基二甲氧基矽烷、3-氯丙基三甲氧基矽烷、3-甲基丙烯醯氧基丙基三甲氧基矽烷、3-巰基丙基三甲氧基矽烷等之密著促進劑;2,2-硫雙(4-甲基-6-t-丁基酚)、2,6-二-t-丁基酚等之防氧化劑;2-(3-t-丁基-5-甲基-2-羥基苯基)-5-氯苯并三唑、烷氧基二苯甲酮類等之紫外線吸收劑;聚丙烯酸鈉等之凝集抑制劑;丙二酸、己二酸、伊康酸、檸康酸、延胡索酸、中康酸、2-胺基乙醇、3-胺基-1-丙醇、5-胺基-1-戊醇、3-胺基-1,2-丙烷二醇、2-胺基-1,3-丙烷二醇、4-胺基-1,2-丁烷二醇等之殘渣改善劑等。
本發明中,著色感光性樹脂組成物可藉由適宜之方法調製。作為較佳著色感光性樹脂組成物之調製方法,可舉例使有機顏料在溶劑中、上述式(1)所表示之化合物及應需要添加之其分散劑的存在下,依據情況與鹼可
溶性樹脂的一部分一同,例如使用珠磨機、輥磨機等,一邊粉碎一邊混合‧分散成為分散液,接著,於此分散液中,添加鹼可溶性樹脂、光聚合性單體、光聚合起始劑,及應需要進一步追加之溶劑或添加劑,藉由混合調製的方法。
依據如此調製之著色感光性樹脂組成物,可形成色調良好、對比率高、耐熱性亦優異、對玻璃基板之密著性提升的像素,且該著色感光性樹脂組成物之保存穩定性及鹼顯像性亦優異。
本發明之彩色濾光片,為具備使用本發明之著色感光性樹脂組成物所形成之著色層者。可於玻璃基板上或預先形成有期望圖型之遮光層的玻璃基板上,使用著色感光性樹脂組成物形成塗膜,對於該塗膜特定圖型狀照射輻射線,藉由顯像,形成彩色濾光片之像素。
本發明之彩色液晶顯示元件,為具備本發明之彩色濾光片者。
以下,基於本發明之實施例進一步具體地說明,但本發明並不限制於此等之實施例。
作為上述式(1)所表示之化合物,準備了下述式所表
示之化合物1。此化合物1之合成法表示於下述。
將3-(4-甲氧基苯基)丙烯酸氯化物5.90g(30mmol)溶解於50ml之乾燥的醚,加入三乙基胺4.59ml(當量比1.1)、二乙基胺2.41ml(當量比1.1),於室溫攪拌1小時。以水50ml、飽和NaHCO3水溶液50ml及1N鹽酸洗淨後,以硫酸鎂乾燥,在減壓下濃縮。以己烷-乙酸乙酯作為展開溶劑,以矽膠支持支撐載體藉由管柱層析法進行純化,得到對應之化合物1(4.65g,20mmol)。丙烯酸氯化物基準之產率為67%。
具備冷卻管及攪拌機之燒瓶中,饋入2,2’-偶氮雙(2,4-二甲基戊腈)1質量份及丙二醇單甲基醚乙酸酯200質量份,連續地饋入甲基丙烯酸15質量份、苯乙烯15質量份、苄基甲基丙烯酸酯35質量份、甘油單甲基丙烯酸酯10質量份、N-苯基順丁烯二醯亞胺25質量份及作為連鎖移動劑之α-甲基苯乙烯二聚體2.5質量份經氮氣取代。之後緩慢攪拌,將反應溶液之溫度升溫至80℃,保持此溫度3小時進行聚合。其後,藉由使反應溶液之溫度升溫至
100℃,加入2,2’-偶氮雙(2,4-二甲基戊腈)0.5質量份,進而聚合1小時,得到黏合劑樹脂溶液(固體成分濃度=33.0%)。得到之樹脂為Mw=10,000、Mn=6,000。此樹脂作為鹼可溶性樹脂(D1)。
將作為有機顏料之色素紅254:15質量份、化合物1:5質量份、市售分散劑之S76500(Lubrizol(股)公司製)5質量份(以固體成分換算)、作為溶劑之丙二醇單甲基醚乙酸酯75質量份藉由珠磨機處理,調製有機顏料分散液(A-1)。
將得到之有機顏料分散液(A-1)100質量份、鹼可溶性樹脂(D1)50質量份(以固體成分換算)、作為光聚合性單體之二新戊四醇六丙烯酸酯30質量份、作為光聚合起始劑之下述式所表示之肟酯化合物10質量份、及作為溶劑之丙二醇單甲基醚乙酸酯混合,調製固體成分濃度15質量%之著色感光性樹脂組成物(CR1)。
將著色感光性樹脂組成物(CR1),於玻璃基板上,使用旋轉塗佈機塗佈後,以80℃之熱板10分鐘進行預烘焙形成塗膜。藉由改變旋轉塗佈機之迴轉數之同樣的操作,形成膜厚相異的3張塗膜。
接著,將此等之基板冷卻至室溫之後,使用高壓水銀燈,對各塗膜以包含365nm、405nm及436nm之各波長的輻射線以2,000J/m2之曝光量曝光。其後,對於此等之基板,藉由將23℃之0.04質量%氫氧化鉀水溶液所成之顯像液以顯像壓1kgf/cm2(噴嘴徑1mm)吐出,進行90秒鐘淋浴顯像。之後,此基板以超純水洗淨,風乾後,進一步於220℃之潔淨烘箱內進行30分鐘之後烘焙,形成評估用硬化膜。
關於得到之3張硬化膜,使用彩色分析儀(使用大塚電子(股)製MCPD2000),以C光源、2度視野,測定CIE表色系中之色度座標值(x、y)。由測定結果求出色度座標值x=0.650之色度座標值y,求出刺激值(Y)。評估結果表示於表1。
進而,形成有硬化膜之基盤以2片偏轉板夾住,由背面側以螢光燈(波長範圍380~780nm)照射的同時使前面側之偏向板迴轉,藉由亮度計LS-100(Minolta(股)製)測定透過之光強度的最大值及最小值。接著,關於每個硬化膜,將最大值以最小值除的值作為對比率。由測定結果求出色度座標值x=0.650之對比率。評估結果表示於表1。
將著色感光性樹脂組成物(CR1)於玻璃基板上使用旋轉塗佈機塗佈後,以80℃之熱板進行10分鐘預烘焙形成膜厚2.5μm之塗膜。
接著,此基板冷卻至室溫之後,使用高壓水銀燈,對各塗膜以包含365nm、405nm及436nm之各波長的輻射線以2,000J/m2之曝光量曝光。其後,對於此等之基板,藉由將23℃之0.04質量%氫氧化鉀水溶液所成之顯像液以顯像壓1kgf/cm2(噴嘴徑1mm)吐出,進行90秒鐘淋浴顯像。其後,此基板以超純水洗淨,風乾後,進一步於270℃之潔淨烘箱內進行60分鐘後烘焙,形成評估用硬化膜。
得到之硬化膜上之相異3處以光學顯微鏡(倍率:200倍)觀測,確認異物之有無。於表1顯示一視野中所觀測之異物的個數。若像素上附著有異物,例如成為色度特性惡化或對比降低之原因。
著色感光性樹脂組成物(CR1)之調製後隨即之黏度,使用E型黏度計(東京計器製)測定。又,著色感光性樹脂組成物(CR1)填充至遮光玻璃容器,在密閉狀態於23℃靜置14日後,使用E型黏度計再度測定黏度。接著,算出相對於調製後隨即之黏度而言14日保存後黏度的增加率,以增加率未滿5%之情形為「A」、5%以上未滿10%之情形為「B」、10%以上之情形為「C」來評估。評估結果表示於表1。
關於著色感光性樹脂組成物(CR1)之對玻璃基板之密著性,以顯像後之最小密著圖型尺寸的大小來評估。顯像後之最小密著圖型尺寸,1μm以上未滿5μm之情形為「A」、5μm以上未滿10μm之情形為「B」、10μm以上未滿15μm之情形為「C」、15μm以上未滿20μm之情形為「D」。評估結果表示於表1。
實施例1中,除用於有機顏料分散液之調製的化合物1變更為1,8-二吖雙環〔5.4.0〕十一-7-烯以外,與實施例1同樣地調製有機顏料分散液(A-2)。接著,使用(A-2)代替有機顏料分散液(A-1)外,其他與實施例1同樣地調製著色感光性樹脂組成物(CR2)。關於著色感光性樹脂組成
物(CR2),與(CR1)同樣,進行色度特性、對比率、耐熱性、保存穩定性、對玻璃基板之密著性的評估。評估結果表示於表1。
由表1可明白,含有上述式(1)所表示之化合物之著色感光性樹脂組成物,為色度特性、對比率、耐熱性、保存穩定性優異,進一步對玻璃基板之密著性高的組成物。
Claims (3)
- 一種著色感光性樹脂組成物,其係含有鹼可溶性樹脂、光聚合性單體、光聚合起始劑、下述式(1)所表示之化合物、有機顏料、及聚胺甲酸酯系分散劑,前述光聚合起始劑為下述式(2)所表示之肟酯化合物,
- 一種彩色濾光片,其具備使用如請求項1之著色感光性樹脂組成物所形成之著色層。
- 一種彩色液晶顯示元件,其具備如請求項2之彩色濾光片。
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TW201305732A (zh) * | 2011-06-24 | 2013-02-01 | Tokyo Ohka Kogyo Co Ltd | 新穎化合物 |
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KR102004550B1 (ko) | 2019-10-01 |
JP2014126677A (ja) | 2014-07-07 |
TW201439671A (zh) | 2014-10-16 |
JP6157111B2 (ja) | 2017-07-05 |
KR20140083909A (ko) | 2014-07-04 |
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