TW202138404A - 感光性樹脂組成物、硬化物、彩色濾光片、顯示裝置用構件及顯示裝置 - Google Patents
感光性樹脂組成物、硬化物、彩色濾光片、顯示裝置用構件及顯示裝置 Download PDFInfo
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- TW202138404A TW202138404A TW110108157A TW110108157A TW202138404A TW 202138404 A TW202138404 A TW 202138404A TW 110108157 A TW110108157 A TW 110108157A TW 110108157 A TW110108157 A TW 110108157A TW 202138404 A TW202138404 A TW 202138404A
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- photosensitive resin
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- RWVGQQGBQSJDQV-UHFFFAOYSA-M sodium;3-[[4-[(e)-[4-(4-ethoxyanilino)phenyl]-[4-[ethyl-[(3-sulfonatophenyl)methyl]azaniumylidene]-2-methylcyclohexa-2,5-dien-1-ylidene]methyl]-n-ethyl-3-methylanilino]methyl]benzenesulfonate Chemical compound [Na+].C1=CC(OCC)=CC=C1NC1=CC=C(C(=C2C(=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C)C=2C(=CC(=CC=2)N(CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C)C=C1 RWVGQQGBQSJDQV-UHFFFAOYSA-M 0.000 description 1
- UWGCNDBLFSEBDW-UHFFFAOYSA-M sodium;4-[[4-(diethylamino)phenyl]-(4-diethylazaniumylidenecyclohexa-2,5-dien-1-ylidene)methyl]naphthalene-2,7-disulfonate Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C2=CC=C(C=C2C=C(C=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 UWGCNDBLFSEBDW-UHFFFAOYSA-M 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
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- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
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- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- VOCBWIIFXDYGNZ-IXKNJLPQSA-N testosterone enanthate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)CCCCCC)[C@@]1(C)CC2 VOCBWIIFXDYGNZ-IXKNJLPQSA-N 0.000 description 1
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- 229910052719 titanium Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- JFZKOODUSFUFIZ-UHFFFAOYSA-N trifluoro phosphate Chemical compound FOP(=O)(OF)OF JFZKOODUSFUFIZ-UHFFFAOYSA-N 0.000 description 1
- KQBSGRWMSNFIPG-UHFFFAOYSA-N trioxane Chemical compound C1COOOC1 KQBSGRWMSNFIPG-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
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- 235000013799 ultramarine blue Nutrition 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
- 239000001052 yellow pigment Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
本揭示係關於一種感光性樹脂組成物、硬化物、彩色濾光片、顯示裝置用構件及顯示裝置。本案主張2020年3月9日於日本申請之日本特願2020-039964號及日本特願2020-039965號之優先權並援用其內容。
就製造絕緣膜、彩色濾光片、彩色濾光片保護膜、微透鏡時所使用之感光性樹脂組成物而言,已知有含有鹼可溶性樹脂、光聚合性化合物、及光聚合起始劑之樹脂組成物、及更含有著色劑(顏料或染料)之樹脂組成物。
專利文獻1及4中,作為前述鹼可溶性樹脂者已揭示含有甲基丙烯酸及甲基丙烯酸環氧丙酯作為構成單體之共聚物。專利文獻2及5中,作為前述鹼可溶性樹脂者已揭示含有甲基丙烯酸及丙烯酸3,4-環氧基三環[5.2.1.02,6]癸酯作為構成單體之共聚物。專利文獻3中,作為前述鹼可
溶性樹脂者已揭示含有甲基丙烯酸及甲基丙烯酸苄酯作為構成單體之共聚物。
[先前技術文獻]
[專利文獻]
專利文獻1:日本特開平11-133600號公報。
專利文獻2:日本特開2006-171160號公報。
專利文獻3:日本特開平9-134004號公報。
專利文獻4:日本特開2011-237728號公報。
專利文獻5:日本特開2007-333847號公報。
但是,專利文獻1及4所揭示之感光性樹脂組成物具有經時增黏等穩定性較低之缺點。又,硬化物之耐溶劑性不充分。專利文獻2及5所揭示之感光性樹脂組成物雖然保存穩定性優異,但與羧酸的反應性差,需要230℃以上之硬化溫度。專利文獻3所揭示之感光性樹脂組成物有硬化物之耐溶劑性較低之缺點。
因此,本揭示之發明之目的為提供一種保存穩定性優異、硬化反應性優異、且硬化物之耐溶劑性優異之感光性樹脂組成物。
又,本揭示之發明之其他目的為提供一種具有上述特性之感光性樹脂組成物之硬化物、該硬化物之彩色濾光片、及具備該彩色濾光片之顯示裝置用構件或顯示裝置。
本發明者為了達成上述目的而努力檢討之結果,發現一種感光性樹脂組成物,係使用含有特定構成單元且發熱峰頂溫度為180至220℃之共聚物作為鹼可溶性樹脂,而可使保存穩定性優異、可以較低溫度硬化、且硬化物之耐溶劑性優異。本揭示之發明係根據該等發現而完成者。
亦即,本揭示提供一種感光性樹脂組成物,係含有鹼可溶性樹脂、光聚合性化合物、光聚合起始劑、及溶劑,其中,
該鹼可溶性樹脂係含有源自於不飽和羧酸或其酐之構成單元(A)及源自於下述式(1)所示化合物之構成單元(B),且使用示差掃描熱量計以5℃/分鐘之速度升溫時所顯示發熱峰頂溫度為180至220℃的共聚物,
(式中,R1及R2分別相同或相異地表示氫原子或碳數1至7之烷基,X表示單鍵或可含有雜原子之2價烴基,Y表示可具有碳數1至3之烷基作為取代基之亞甲基或伸乙基、氧原子、或可與氧原子鍵結之硫原子,n表示0至7之整數。)
前述共聚物可更含有源自選自於下述(c1)至(c4)所成群組之至少1種化合物之構成單元(C),
(c1)可經烷基取代之苯乙烯;
(c2)N-取代順丁烯二醯亞胺;
(c3)N-乙烯基化合物;
(c4)下式(2)所示之不飽和羧酸衍生物。
(式中,R11表示氫原子或碳數1至7之烷基,R12表示可含有雜原子之烴基,Z表示雜原子)
相對於前述共聚物之全構成單元,前述構成單元(A)之比例可為2至60重量%,前述構成單元(B)之比例可為40至98重量%,前述構成單元(C)之比例可為0至85重量%。
本揭示之感光性樹脂組成物可更含有色材。
前述色材可為顏料及/或染料。
又,本揭示提供一種前述感光性樹脂組成物之硬化物。
又,本揭示提供一種彩色濾光片,係前述感光性樹脂組成物之硬化物。
本揭示提供一種顯示裝置用構件或顯示裝置,係具備前述彩色濾光片。
根據本揭示之發明可提供一種保存穩定性優異、硬化反應性優異、且硬化物之耐溶劑性優異之感光性樹脂組成物。又,可提供一種具有上述特性之感光性樹脂組成物之硬化物、該硬化物之彩色濾光片、及具備該彩色濾光片之顯示裝置用構件或顯示裝置。
本揭示之感光性樹脂組成物主要係作為絕緣膜、彩色濾光片保護膜、微透鏡、著色圖案等之形成材料、透明膜使用者,並含有含有鹼可溶性樹脂、光聚合性化合物、光聚合起始劑、及溶劑。又,本揭示之感光性樹脂組成物可進一步含有色材。
<鹼可溶性樹脂>
本揭示中,鹼可溶性樹脂係使用含有源自於不飽和羧酸或其酐之構成單元(A)及源自於前述式(1)所示化合物之構成單元(B),且使用示差掃描熱量計以5℃/分鐘之速度升溫時所顯示發熱峰頂溫度為180至220℃之共聚物。前述共聚物可進一步含有源於選自於前述(c1)至(c4)所成群組之至少1種化合物之構成單元(C)。又,可進一步含有後述構成單元(D)作為構成單元(A)至(C)以外之構成單元。
[構成單元(A)]
構成單元(A)係可藉由將不飽和羧酸或其酸酐(a)進行共聚合而導入於共聚物。
不飽和羧酸或其酸酐(a)並無特別限定,可舉例如:丙烯酸、甲基丙烯酸、巴豆酸等α,β-不飽和單羧酸;伊康酸、順丁烯二酸、反丁烯
二酸等α,β-不飽和二羧酸;甲基丙烯酸酐等α,β-不飽和單羧酸之酐;順丁烯二酸酐、伊康酸酐等α,β-不飽和二羧酸之酐。該等中,以共聚性或顯影性之觀點而言,特佳為丙烯酸、甲基丙烯酸。不飽和羧酸或其酸酐(a)可單獨使用或組合2種以上使用。
相對於前述共聚物之全構成單元,構成單元(A)之比例(含量)並無特別限定,例如較佳為2至60重量%,更佳為3至40重量%,又更佳為5至20重量%。藉由使構成單元(A)之比例在上述範圍內,而有硬化物之耐溶劑性或顯影性較優異之傾向。此外,本揭示中,構成單元的共聚物所佔比例是指以共聚所使用之化合物(單體)重量為基準者。例如,相對於共聚所使用之化合物總量(100重量%),構成單元(A)之共聚物所佔比例意指不飽和羧酸或其酸酐(a)之使用量比例。
[構成單元(B)]
構成單元(B)可藉由將下式(1)所示化合物進行共聚合而導入於共聚物。
式(1)中,R1及R2分別相同或相異地表示氫原子或碳數1至7之烷基。X表示單鍵或可含有雜原子之2價烴基。Y表示可具有碳數1至3之烷基作為取代基之亞甲基或伸乙基、氧原子、或可與氧原子鍵結之硫原子。n表示0至7之整數。
R1及R2中的碳數1至7之烷基可舉例如:甲基、乙基、丙基、異丙基、丁基、異丁基、第二丁基、戊基、己基、庚基等。n為2以上時,n個R2可相同亦可相異。以共聚性或反應性之觀點而言,R1及R2較佳為氫原子、甲基、或乙基。
X之可含有雜原子之2價烴基中,雜原子可鍵結於烴基末端,也可介於構成烴基之碳原子間。雜原子並無特別限定,可舉例如:氮原子、氧原子、硫原子。
前述可含有雜原子之2價烴基可舉例如:亞甲基、伸乙基、伸丙基、三亞甲基等伸烷基(較佳為碳數1至12之伸烷基,更佳為碳數1至6之伸烷基,又更佳為碳數1至3之伸烷基);硫亞甲基、硫伸乙基、硫伸丙基等硫伸烷基(較佳為碳數1至12之硫伸烷基,更佳為碳數1至6之硫伸烷基);胺基亞甲基、胺基伸乙基、胺基伸丙基等胺基伸烷基(較佳為碳數1至12之胺基伸烷基,更佳為碳數1至6之胺基伸烷基)等。其中,以保存穩定性之觀點而言,較佳為碳數1至3之伸烷基,更佳為亞甲基。
Y之可具有碳數1至3之烷基作為取代基之亞甲基或伸乙基並無特別限定,較佳為亞甲基或伸乙基,更佳為亞甲基。
Y之可與氧原子鍵結之硫原子可舉例如:硫原子、磺醯基等。
前述式(1)所示化合物可舉例如下式(1a)所示化合物。
式(1a)中的R1、R2、X、Y、及n同式(1)所說明者。
式(1)所示化合物之具體例可舉出下列化合物。
相對於前述共聚物之全構成單元,構成單元(B)之比例(含量)並無特別限定,較佳為40至98重量%,更佳為60至95重量%,又更佳為75至90重量%。藉由使構成單元(B)之比例在上述範圍內,而有硬化物之耐溶劑性或顯影性較優異之傾向。
[構成單元(C)]
構成單元(C)為源自選自於可經烷基取代之苯乙烯(c1)、N-取代順丁烯二醯亞胺(c2)、N-乙烯基化合物(c3)、及前述式(2)所示之不飽和羧酸衍生物(c4)所成群組之至少1種化合物的構成單元。構成單元(C)具有賦予硬化物(硬化皮膜)硬度之功能、或使共聚反應平穩化之功能、提高對溶劑之溶解性之功能、提高與基材的密著性之功能等。
構成單元(C)可藉由將選自由前述(c1)至(c4)所成群組之至少1種化合物進行共聚合而導入於共聚物。
(苯乙烯(c1))
可經烷基取代之苯乙烯(c1)中的烷基並無特別限定,可舉例如:甲基、乙基、丙基、異丙基、丁基、異丁基、第三丁基、己基等碳數1至7之烷基。該等中較佳為甲基或乙基等碳數1至4之烷基,更佳為甲基。前述烷基可鍵結於苯乙烯之乙烯基及苯環之任一者。
可經烷基取代之苯乙烯(c1)之代表例可舉出:苯乙烯、α-甲基苯乙烯、乙烯基甲苯(鄰乙烯基甲苯、間乙烯基甲苯、對乙烯基甲苯)等。可經烷基取代之苯乙烯(c1)可單獨使用或組合2種以上使用。
(N-取代順丁烯二醯亞胺(c2))
N-取代順丁烯二醯亞胺(c2)可舉例如下式(3)所示之化合物。
式(3)中,R21表示有機基。
前述有機基可舉例如:烴基、雜環基。烴基可舉例如:甲基、乙基、丙基、異丙基、丁基、己基等烷基(例如C1-6烷基等);環戊基、環己基、環辛基、金剛烷基、降莰基等環烷基;苯基等芳基;苄基等芳烷基;該等2種以上鍵結而成的基等。雜環基可舉例如:含有選自氮原子、氧原子、及硫原子所成群組中之至少1種雜原子之5至10員之雜環烷基及雜芳基。
N-取代順丁烯二醯亞胺(c2)並無特別限定,可舉例如:N-甲基順丁烯二醯亞胺、N-乙基順丁烯二醯亞胺、N-丙基順丁烯二醯亞胺等N-烷基順丁烯二醯亞胺;N-環戊基順丁烯二醯亞胺、N-環己基順丁烯二醯亞胺、N-環辛基順丁烯二醯亞胺、N-金剛烷基順丁烯二醯亞胺、N-降莰基順丁烯二醯亞胺等N-環烷基順丁烯二醯亞胺;N-苯基順丁烯二醯亞胺等N-芳基順丁烯二醯亞胺;N-苄基順丁烯二醯亞胺等N-芳烷基順丁烯二醯亞胺等。N-取代順丁烯二醯亞胺(c2)可單獨使用或組合2種以上使用。
(N-乙烯基化合物(c3))
N-乙烯基化合物(c3)並無特別限定,可舉例如:N-乙烯基甲醯胺、N-乙烯基乙醯胺、N-乙烯基異丙醯胺、N-乙烯基-N-甲基乙醯胺、N-乙烯基吡
咯啶酮、N-乙烯基咔唑、N-乙烯基哌啶酮、N-乙烯基己內醯胺等。N-乙烯基化合物(c3)可單獨使用或組合2種以上使用。
(不飽和羧酸衍生物(c4))
不飽和羧酸衍生物(c4)可為下式(2)所示。
式(2)中,R11表示氫原子或碳數1至7之烷基。R12表示可含有雜原子之烴基。Z表示雜原子。
R11中的碳數1至7之烷基可舉例如:甲基、乙基、丙基、異丙基、丁基、異丁基、第三丁基、己基等。R11特佳為氫原子或甲基。
R12中的可含有雜原子之烴基可舉例如:烷基、雜烷基、烯基、環烷基、雜環烷基、芳基、及該等2個以上連結而成的基。前述作為雜原子可舉例如:氮原子、氧原子、硫原子。
前述烷基可舉例如:甲基、乙基、丙基、異丙基、丁基、異丁基、第二丁基、己基、辛基、癸基、十二烷基、異癸基、月桂基、硬脂基等碳數1至23之烷基。
前述雜烷基可舉例如:-(R13-O)m-R14基(式中,R13表示為碳數1至12之伸烷基,R14表示氫原子或碳數1至12之烷基,m表示1以上之整數)、-R15-NR16R17基(式中,R15表示為碳數1至12之伸烷基,R16及R17分別相同或相異地表示氫原子或碳數1至4之烷基)。
前述烯基可舉例如:烯丙基、3-丁烯基、5-己烯基等碳數2至23之烯基。
前述環烷基可舉例如:環戊基、環己基、環辛基、金剛烷基、降莰基等碳數3至12之環烷基。
前述雜環烷基可舉例如:氧環丁烷環、四氫呋喃環、四氫吡喃環、氧雜環庚烷環等含有環狀醚結構的基(例如,含有3員環以上之環狀醚的基)等。
前述芳基可舉例如:苯基、萘基等碳數6至12之芳基。
式(2)所示之不飽和羧酸衍生物(c4)並無特別限定,可舉例如:(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)丙烯酸異癸酯、(甲基)丙烯酸月桂酯、(甲基)丙烯酸硬脂酯等具有烷基之(甲基)丙烯酸酯;(甲基)丙烯酸N,N-二甲基胺基乙酯、(甲基)丙烯酸N,N-二乙基胺基乙酯、(甲基)丙烯酸N,N-二異丙基胺基乙酯等具有烷基胺基之(甲基)丙烯酸酯;(甲基)丙烯酸2-羥基乙酯、(甲基)丙烯酸2-羥基丙酯、(甲基)丙烯酸2-羥基丁酯、(甲基)丙烯酸4-羥基丁酯等含有羥基之(甲基)丙烯酸酯;甲氧基二乙二醇(甲基)丙烯酸酯、乙氧基二乙二醇(甲基)丙烯酸酯、異辛基氧二乙二醇(甲基)丙烯酸酯、苯氧基三乙二醇(甲基)丙烯酸酯、甲氧基三乙二醇(甲基)丙烯酸酯、甲氧基聚乙二醇(甲基)丙烯酸酯等聚烷二醇(甲基)丙烯酸酯等具有雜烷基之(甲基)丙烯酸酯;(甲基)丙烯酸烯丙酯等具有烯基之(甲基)丙烯酸酯;(甲基)丙烯酸環己酯、1-(甲基)丙烯酸金剛烷酯、(甲基)丙烯酸異莰酯、三環[5,2,1,02,6]癸烷-8-醇(甲基)丙烯酸酯等具有單環或多環之環烷基之(甲基)
丙烯酸酯;(甲基)丙烯酸環氧丙酯、(甲基)丙烯酸2-甲基環氧丙酯、(甲基)丙烯酸2-乙基環氧丙酯、(甲基)丙烯酸2-環氧丙基氧基乙酯、(甲基)丙烯酸3-環氧丙基氧基丙酯、(甲基)丙烯酸環氧丙基氧基苯酯等具有環氧基(環氧乙烷基)之(甲基)丙烯酸酯;(甲基)丙烯酸氧基環丁酯、(甲基)丙烯酸3-甲基-3-氧基環丁酯、(甲基)丙烯酸3-乙基-3-氧基環丁酯、(甲基)丙烯酸(3-甲基-3-氧基環丁基)甲酯、(甲基)丙烯酸(3-乙基-3-氧基環丁基)甲酯、(甲基)丙烯酸2-(3-甲基-3-氧基環丁基)乙酯、(甲基)丙烯酸2-(3-乙基-3-氧基環丁基)乙酯、(甲基)丙烯酸2-[(3-甲基-3-氧基環丁基)甲基氧基]乙酯、(甲基)丙烯酸2-[(3-乙基-3-氧基環丁基)甲基氧基]乙酯、(甲基)丙烯酸3-[(3-甲基-3-氧基環丁基)甲基氧基]丙酯、(甲基)丙烯酸3-[(3-乙基-3-氧環丁基)甲基氧基]丙酯等具有氧基環丁基之(甲基)丙烯酸酯;(甲基)丙烯酸四氫糠酯等具有四氫呋喃基之(甲基)丙烯酸酯;(甲基)丙烯酸3,4-環氧基環己酯、(甲基)丙烯酸3,4-環氧基環己基甲酯、(甲基)丙烯酸2-(3,4-環氧基環己基)乙酯、(甲基)丙烯酸2-(3,4-環氧基環己基甲基氧)乙酯、(甲基)丙烯酸3-(3,4-環氧基環己基甲基氧)丙酯等含有脂環式環氧基之(甲基)丙烯酸酯等具有雜環烷基(例如,含有3員環以上之環狀醚的基)之(甲基)丙烯酸酯;(甲基)丙烯酸苯酯、(甲基)丙烯酸苄酯等具有芳基之(甲基)丙烯酸酯;3-(甲基)丙烯醯氧基丙基甲基二甲氧基矽烷、3-(甲基)丙烯醯氧基丙基三甲氧基矽烷、3-(甲基)丙烯醯氧基丙基甲基二乙氧基矽烷、3-(甲基)丙烯醯氧基丙基三乙氧基矽烷、8-(甲基)丙烯醯氧基辛基三甲氧基矽烷等含有烷氧基矽基之(甲基)丙烯酸酯。式(2)所示之不飽和羧酸衍生物(c4)可單獨使用或組合2種以上使用。
相對於前述共聚物之全構成單元,構成單元(C)之比例(含量)並無特別限定,較佳為0至85重量%,更佳為1至60重量%,又更佳為2至40重量%。藉由使構成單元(C)之比例為上述範圍內,有硬化物之耐溶劑性較優異之傾向。
[構成單元(D)]
本揭示中的前述共聚物可含有前述構成單元(A)至(C)以外之構成單元(D)。構成單元(D)可舉例如源自(甲基)丙烯醯胺、(甲基)丙烯腈之構成單元。
本揭示中的前述共聚物含有構成單元(A)及構成單元(B)且不含有構成單元(C)時,相對於全構成單元,構成單元(A)及構成單元(B)的總量較佳為90重量%以上,更佳為95重量%以上,又更佳為99重量%以上,實質上可為100重量%。又,本揭示中的前述共聚物含有構成單元(A)、構成單元(B)及構成單元(C)時,相對於全構成單元,構成單元(A)至(C)之總量較佳為90重量%以上,更佳為95重量%以上,又更佳為99重量%以上,實質上可為100重量%。
共聚物之重量平均分子量(Mw)並無特別限定,例如較佳為1000至1000000,更佳為3000至300000,又更佳為5000至100000。共聚物之分子量分佈(重量平均分子量與數平均分子量之比:Mw/Mn)並無特別限定,例如較佳為5.0以下,更佳為1.0至4.5,又更佳為1.0至4.0。此外,本揭示中,重量平均分子量(Mw)及數平均分子量(Mn)例如可以GPC且使用聚苯乙烯作為標準物質進行測定,但較佳為以實施例所使用之方法測定者。
本揭示中的前述聚合物使用示差掃描熱量計以5℃/分鐘之速度升溫時所顯示之發熱峰頂溫度為180至220℃。此外,本揭示中,發熱峰頂溫度例如較佳為以後述實施例所使用之方法測定者。
本揭示中的前述共聚物係作為本揭示之感光性樹脂組成物之黏合劑樹脂發揮功能。
<共聚物之製造方法>
本揭示中的前述共聚物係可藉由將不飽和羧酸或其酐(a)、含有環上具有環氧基之多環式脂肪族基及具有不飽和鍵的基之化合物(b)、因應所需選自前述(c1)至(c4)所成群組中之至少1種化合物、及對應前述構成單元(D)之化合物進行共聚合而製造。以下,將不飽和羧酸或其酐(a)等可導入至共聚物之化合物合稱為「單體」。
本揭示之共聚物之製造方法中可在聚合起始劑存在下進行共聚。前述聚合起始劑可使用慣用或公知的自由基聚合起始劑,可舉例如:2,2'-偶氮雙異丁腈、2,2’-偶氮雙(2,4-二甲基戊腈)、2,2’-偶氮雙(4-甲氧基-2,4-二甲基戊腈)、二甲基-2,2’-偶氮雙(2-甲基丙酸酯)、二乙基-2,2’-偶氮雙(2-甲基丙酸酯)、二丁基-2,2’-偶氮雙(2-甲基丙酸酯)等偶氮化合物;過氧化苯甲醯、過氧化月桂醯、過氧新戊酸第三丁酯、1,1-雙(過氧第三丁基)環己烷等有機過氧化物;過氧化氫等。使用過氧化物作為自由基聚合起始劑時,可組合還原劑而作為氧化還原型起始劑。其中較佳為偶氮化合物,更佳為2,2’-偶氮雙異丁腈、2,2’-偶氮雙(2,4-二甲基戊腈)、二甲基-2,2’-偶氮雙(2-甲基丙酸酯)。
聚合起始劑之使用量可在不損及平穩共聚之範圍內適當地選擇並無特別限定,例如,相對於單體之總量(100重量份),較佳為1至20重量份,更佳為3至15重量份。
本揭示中,共聚合可藉由溶液聚合、塊狀聚合、懸浮聚合、塊狀/懸浮聚合、乳化聚合等製造丙烯酸系聚合物或苯乙烯系聚合物時使用之慣用方法而進行。單體、聚合起始劑分別可一起供給於反應系統,也可將其一部分或全部滴入於反應系統。例如可採用:於保持於固定溫度之單體或單體與聚合溶劑的混合液中,滴下於聚合溶劑溶解有聚合起始劑而成的溶液之聚合方法;或將預先於聚合溶劑溶解有單體、聚合起始劑而成之溶液,滴下於保持在固定溫度之聚合溶劑中之聚合方法(滴下聚合法)等。
本揭示中的前述共聚物較佳為在聚合溶劑中共聚合。聚合溶劑可因應單體組成等而適當地選擇,可舉例如:醚(二乙基醚;乙二醇單或二烷基醚、二乙二醇單或二烷基醚、丙二醇單或二烷基醚、丙二醇單或二芳基醚、二丙二醇單或二烷基醚、三丙二醇單或二烷基醚、1,3-丙二醇單或二烷基醚、1,3-丁二醇單或二烷基醚、1,4-丁二醇單或二烷基醚、甘油單或二或三烷基醚等二醇醚類等鏈狀醚;四氫呋喃、二噁烷等環狀醚等)、酯(乙酸甲酯、乙酸乙酯、乙酸丁酯、乙酸異戊酯、乳酸乙酯、3-甲氧基丙酸甲酯、3-乙氧基丙酸乙酯、C5-6環烷二醇單或二乙酸酯、C5-6環烷二甲醇單或二乙酸酯等羧酸酯類;乙二醇單烷基醚乙酸酯、乙二醇單或二乙酸酯、二乙二醇單烷基醚乙酸酯、二乙二醇單或二乙酸酯、丙二醇單烷基醚乙酸酯、丙二醇單或二乙酸酯、二丙二醇單烷基醚乙酸酯、二丙二醇單或二乙酸酯、1,3-丙二醇單烷基醚乙酸酯、1,3-丙二醇單或二乙酸酯、1,3-丁二醇單烷基
醚乙酸酯、1,3-丁二醇單或二乙酸酯、1,4-丁二醇單烷基醚乙酸酯、1,4-丁二醇單或二乙酸酯、甘油單或二或三乙酸酯、甘油單或二C1-4烷基醚二或單乙酸酯、三丙二醇單烷基醚乙酸酯、三丙二醇單或二乙酸酯等二醇乙酸酯類或二醇醚乙酸酯類等)、酮(丙酮、甲基乙基酮、甲基異丁基酮、環己酮、3,5,5-三甲基-2-環己烯-1-酮等)、醯胺(N,N-二甲基乙醯胺、N,N-二甲基甲醯胺等)、亞碸(二甲基亞碸等)、醇(甲醇、乙醇、丙醇、C5-6環烷二醇、C5-6環烷二甲醇等)、烴(苯、甲苯、二甲苯等芳香族烴、己烷等脂肪族烴、環己烷等脂環式烴等)、該等之混合溶劑等。
聚合溫度係可因應單體之種類或組成適當地選擇,並無特別限定,例如較佳為30至150℃。
含有藉由上述方法所得之共聚物之反應溶液可因應所需實施沉殿或再沉殿而精製。沉殿或再沉殿所使用之溶劑可為有機溶劑及水之任一者,也可為其混合溶劑。有機溶劑可舉例如:烴(戊烷、己烷、庚烷、辛烷等脂肪族烴;環己烷、甲基環己烷等脂環式烴;苯、甲苯、二甲苯等芳香族烴)、鹵化烴(二氯甲烷、氯仿、四氯化碳等鹵化脂肪族烴;氯苯、二氯苯等鹵化芳香族烴等)、硝基化合物(硝基甲烷、硝基乙烷等)、腈(乙腈、苯甲腈等)、醚(二乙基醚、二異丙基醚、二甲氧基乙烷等鏈狀醚;四氫呋喃、二噁烷等環狀醚)、酮(丙酮、甲基乙基酮、二異丁基酮等)、酯(乙酸乙酯、乙酸丁酯等)、碳酸酯(碳酸二甲酯、碳酸二乙酯、碳酸伸乙酯、碳酸伸丙酯等)、醇(甲醇、乙醇、丙醇、異丙醇、丁醇等)、羧酸(乙酸等)、及含有該等溶劑之混合溶劑等。
<色材>
本揭示中,色材(著色劑)只要是具有著色性即可,可因應彩色濾光片等用途而適當地選擇色彩或材質。具體而言,色材可使用顏料、染料及天然色素之任一者,在彩色濾光片用途中要求高色純度、亮度、對比等,故較佳為顏料及/或染料。
上述顏料可舉出有機顏料、無機顏料之任一者,有機顏料可舉例如色料索引(C.I.;The Society of Dyersand Colourists公司發行)中分類為顏料之化合物。具體而言可舉出下述色料索引(C.I.)名者。
C.I.顏料黃1、C.I.顏料黃3、C.I.顏料黃12、C.I.顏料黃13、C.I.顏料黃14、C.I.顏料黃16、C.I.顏料黃17、C.I.顏料黃20、C.I.顏料黃24、C.I.顏料黃31、C.I.顏料黃55、C.I.顏料黃83、C.I.顏料黃86、C.I.顏料黃93、C.I.顏料黃94、C.I.顏料黃109、C.I.顏料黃110、C.I.顏料黃117、C.I.顏料黃125、C.I.顏料黃137、C.I.顏料黃138、C.I.顏料黃139、C.I.顏料黃147、C.I.顏料黃148、C.I.顏料黃150、C.I.顏料黃153、C.I.顏料黃154、C.I.顏料黃155、C.I.顏料黃166、C.I.顏料黃168、C.I.顏料黃180、C.I.顏料黃194、C.I.顏料黃211、C.I.顏料黃214等黃色顏料。
C.I.顏料橘5、C.I.顏料橘13、C.I.顏料橘14、C.I.顏料橘24、C.I.顏料橘31、C.I.顏料橘34、C.I.顏料橘36、C.I.顏料橘38、C.I.顏料橘40、C.I.顏料橘42、C.I.顏料橘43、C.I.顏料橘46、C.I.顏料橘49、C.I.顏料橘51、C.I.顏料橘55、C.I.顏料橘59、C.I.顏料橘61、C.I.顏料橘64、C.I.顏料橘65、C.I.顏料橘68、C.I.顏料橘70、C.I.顏料橘71、C.I.顏料橘72、C.I.顏料橘73、C.I.顏料橘74等橘色顏料。
C.I.顏料紅1、C.I.顏料紅2、C.I.顏料紅5、C.I.顏料紅9、C.I.顏料紅17、C.I.顏料紅31、C.I.顏料紅32、C.I.顏料紅41、C.I.顏料紅97、C.I.顏料紅105、C.I.顏料紅122、C.I.顏料紅123、C.I.顏料紅144、C.I.顏料紅149、C.I.顏料紅166、C.I.顏料紅168、C.I.顏料紅170、C.I.顏料紅171、C.I.顏料紅175、C.I.顏料紅176、C.I.顏料紅177、C.I.顏料紅178、C.I.顏料紅179、C.I.顏料紅180、C.I.顏料紅185、C.I.顏料紅187、C.I.顏料紅192、C.I.顏料紅202、C.I.顏料紅206、C.I.顏料紅207、C.I.顏料紅209、C.I.顏料紅214、C.I.顏料紅215、C.I.顏料紅216、C.I.顏料紅220、C.I.顏料紅221、C.I.顏料紅224、C.I.顏料紅242、C.I.顏料紅243、C.I.顏料紅254、C.I.顏料紅255、C.I.顏料紅262、C.I.顏料紅264、C.I.顏料紅265、C.I.顏料紅272等紅色顏料。
C.I.顏料紫1、C.I.顏料紫19、C.I.顏料紫23、C.I.顏料紫29、C.I.顏料紫32、C.I.顏料紫36、C.I.顏料紫38等紫色顏料。
C.I.顏料藍15、C.I.顏料藍15:3、C.I.顏料藍15:4、C.I.顏料藍15:6、C.I.顏料藍60、C.I.顏料藍80等藍色顏料。
C.I.顏料綠7、C.I.顏料綠36、C.I.顏料綠58等綠色顏料。
C.I.顏料棕23、C.I.顏料棕25等棕色顏料。
C.I.顏料黑1、C.I.顏料黑7等黑色顏料。
又,上述無機顏料可舉例如:氧化鈦、硫酸鋇、碳酸鈣、氧化鋅、硫酸鉛、黃色鉛、鋅黃、三氧化二鐵(紅色氧化鐵(III))、鎘紅、群青、普魯士藍、氧化鉻綠、鈷綠、棕土、鈦黑、合成鐵黑、碳黑等。
本揭示中,可藉由將顏料再結晶法、再沉殿法、溶劑洗淨法、昇華法、真空加熱法或該等的組合而精製而使用。又,顏料可將其粒子表面以樹脂改質並使用。
又,上述染料可由各種油溶性染料、直接染料、酸性染料、金屬錯合物染料等適當地選擇,可舉例如下述色料索引(C.I.)名者。
C.I.溶劑黃4、C.I.溶劑黃14、C.I.溶劑黃15、C.I.溶劑黃24、C.I.溶劑黃82、C.I.溶劑黃88、C.I.溶劑黃94、C.I.溶劑黃98、C.I.溶劑黃162、C.I.溶劑黃179、C.I.酸黃17、C.I.酸黃29、C.I.酸黃40、C.I.酸黃76等黃色染料。
C.I.溶劑橘2、C.I.溶劑橘7、C.I.溶劑橘11、C.I.溶劑橘15、C.I.溶劑橘26、C.I.溶劑橘56、C.I.酸橘51、C.I.酸橘63等橘色染料。
C.I.溶劑紅45、C.I.溶劑紅49、C.I.酸紅91、C.I.酸紅92、C.I.酸紅97、C.I.酸紅114、C.I.酸紅138、C.I.酸紅151等紅色染料。
C.I.溶劑藍35、C.I.溶劑藍37、C.I.溶劑藍59、C.I.溶劑藍67、C.I.酸藍80、C.I.酸藍83、C.I.酸藍90等藍色染料。
C.I.酸綠9、C.I.酸綠16、C.I.酸綠25、C.I.酸綠27等綠色染料。
本揭示中色材可單獨使用或混合2種以上使用。
相對於感光性樹脂組成物之固形份,色材含量並無特別限定,例如較佳為3至50重量%,更佳為5至30重量%。在此「固形份」是指例如上述溶劑以外之成分。
本揭示中,使用顏料作為色材時,可因應所需與顏料分散劑、顏料分散助劑一起使用。上述顏料分散劑可舉例如:陽離子系、陰離子系、非離子系、兩性等分散劑(界面活性劑);丙烯酸系共聚物、聚酯、聚胺甲酸乙酯、聚乙烯亞胺、聚烯丙胺等聚合物分散劑。
上述顏料分散劑可使用市售品,可舉例如丙烯酸系共聚物之Disperbyk-2000、Disperbyk-2001、BYK-LPN6919、BYK-LPN21116(以上皆為BYK公司製),聚酯之AJISPER PB821、AJISPER PB822、AJISPER PB880(Ajinomoto Fine-Techno股份有限公司製),聚胺甲酸乙酯之Disperbyk-161、Disperbyk-162、Disperbyk-165、Disperbyk-167、Disperbyk-170、Disperbyk-182(以上皆為BYK公司製)、SOLSPERSE 76500(Lubrizol股份有限公司公司製),聚乙烯亞胺之SOLSPERSE 24000(Lubrizol股份有限公司公司製)等。
該等顏料分散劑可單獨使用或混合2種以上使用。相對於顏料100重量份,顏料分散劑含量通常為100重量份以下,較佳為1至70重量份,更佳為10至70重量份,又更佳為30至60重量份。顏料分散劑含量在上述範圍時,有可獲得均勻分散狀態之顏料分散液之傾向,故較佳。
上述顏料分散助劑可舉例如顏料衍生物,具體而言可舉出:銅酞青素、二酮吡咯并吡咯、喹啉黃之磺酸衍生物等。顏料分散助劑含量可在不阻礙本揭示之發明目的之範圍內適當地決定。
<光聚合性化合物>
本揭示中,光聚合性化合物並無特別限定,可舉例如:多官能乙烯基化合物、多官能硫醇化合物、多官能環氧化合物。
多官能乙烯基化合物只要為具有2個以上乙烯基之化合物則無特別限定,可舉例如:乙二醇、丙二醇等伸烷二醇之二(甲基)丙烯酸酯;聚乙二醇、聚丙二醇等聚烷二醇之二(甲基)丙烯酸酯;兩末端羥基聚丁二烯、兩末端羥基聚異戊二烯、兩末端羥基聚己內酯等兩末端羥基化聚合物之二(甲基)丙烯酸酯;甘油、1,2,4,-丁烷三醇、三羥甲基烷、四羥甲基烷、新戊四醇、二新戊四醇等3價以上多元醇之聚(甲基)丙烯酸酯;3價以上之多元醇之聚烷二醇加成物之聚(甲基)丙烯酸酯;1,4-環己二醇、1,4-苯二醇等環式多元醇之聚(甲基)丙烯酸酯;聚酯(甲基)丙烯酸酯、環氧基(甲基)丙烯酸酯、胺甲酸乙酯(甲基)丙烯酸酯、聚矽氧樹脂(甲基)丙烯酸酯等寡聚(甲基)丙烯酸酯等。該等中較佳為具有2個以上(甲基)丙烯醯基之多官能(甲基)丙烯酸酯。多官能乙烯基化合物可單獨使用或組合2種以上使用。
多官能硫醇化合物只要為具有2個以上硫醇基之化合物則無特別限定,可舉例如:己烷二硫醇、癸烷二硫醇、1,4-丁二醇雙硫丙酸酯、1,4-丁二醇雙硫醇乙酸酯、乙二醇雙硫醇乙酸酯、乙二醇雙硫醇丙酸酯、三羥甲基丙烷三硫醇乙酸酯、三羥甲基丙烷三硫醇丙酸酯、三羥甲基丙烷三(3-巰基丁酸酯)、新戊四醇四硫醇乙酸酯、新戊四醇四硫醇丙酸酯、三巰基丙酸三(2-羥基乙基)異三聚氰酸酯、1,4-二甲基巰基苯、2,4,6-三巰基-s-三、2-(N,N-二丁胺基)-4,6-二巰基-s-三、四乙二醇雙3-巰基丙酸酯、三羥甲基丙烷三3-巰基丙酸酯、三(3-巰基丙炔基氧乙基)異三聚氰酸酯、新
戊四醇四3-巰基丙酸酯、二新戊四醇四3-巰基丙酸酯、1,4-雙(3-巰基丁醯基氧)丁烷、1,3,5-三(3-巰基丁基氧乙基)-1,3,5-三-2,4,6(1H,3H,5H)-三酮、新戊四醇四(3-巰基丁酸酯)等。多官能硫醇化合物可單獨使用或組合2種以上使用。
多官能環氧化合物只要為具有2個以上環氧基之化合物則無特別限定,可舉例如:藉由環氧丙基醚型環氧化合物[多羥基化合物(雙酚類、多價苯酚類、脂環式多元醇類、脂肪族多元醇類等)與環氧氯丙烷的反應而生成之環氧丙基醚類(例如,乙二醇二環氧丙基醚、二乙二醇二環氧丙基醚、聚乙二醇二環氧丙基醚等(聚)C2-4伸烷二醇二環氧丙基醚;間苯二酚、氫醌等多價苯酚類之二環氧丙基醚;環己二醇、環己烷二甲醇、氫化雙酚類等脂環式多元醇類之二環氧丙基醚;雙酚類(4,4’-二羥基聯苯基、雙酚A等雙(羥基苯基)烷類等)或其C2-3環氧烷加成物之二環氧丙基醚等)、酚醛清漆型環氧樹脂(苯酚酚醛清漆型或甲酚酚醛清漆型環氧樹脂等)等]、環氧丙基酯型環氧化合物、脂環族環氧化合物(或環狀脂肪族環氧樹脂)、雜環式環氧樹脂(三環氧丙基異三聚氰酸酯(TGIC)、乙內醯脲型環氧樹脂等)、環氧丙胺型環氧化合物[胺類與環氧氯丙烷的反應生成物,且可舉例如N-環氧丙基芳香族胺{四環氧丙基二胺基二苯基甲烷(TGDDM)、三環氧丙胺基苯酚(TGPAP、TGMAP等)、二環氧丙基苯胺(DGA)、二環氧丙基甲苯胺(DGT)、四環氧丙基二甲苯二胺(TGMXA等)等}、N-環氧丙基脂環族胺(四環氧丙基雙胺基環己烷等)等]等。多官能環氧化合物可單獨使用或組合2種以上使用。
光聚合性化合物可單獨使用或混合2種以上使用。相對於前述鹼可溶性樹脂100重量份,光聚合性化合物含量通常為10至300重量份,較佳為30至200重量份,更佳為40至150重量份。又,感光性樹脂組成物含有色材時,相對於前述色材100重量份,光聚合性化合物含量通常為10至1000重量份,較佳為50至600重量份,更佳為100至500重量份。光聚合性化合物含量在上述範圍時,則可充分地產生硬化且獲得良好之密著性。
<光聚合起始劑>
本揭示中,光聚合起始劑並無特別限定,可舉出光自由基聚合起始劑、光陽離子聚合起始劑。
光自由基聚合起始劑係藉由照射光產生自由基,並開始感光性樹脂組成物所含有之光聚合性化合物的硬化反應(自由基聚合)之化合物。光自由基聚合起始劑可單獨使用或混合2種以上使用。
光自由基聚合起始劑可舉例如:噻噸酮系化合物、苯乙酮系化合物、二咪唑系化合物、三系化合物、肟系化合物、鎓鹽系化合物、安息香系化合物、二苯基酮系化合物、α-二酮系化合物、多核醌系化合物、重氮系化合物、醯亞胺磺酸酯系化合物、蒽系化合物等。
前述噻噸酮系化合物可舉例如:噻噸酮、2-氯噻噸酮、2-甲基噻噸酮、2-異丙基噻噸酮、4-異丙基噻噸酮、2,4-二甲基噻噸酮、2,4-二乙基噻噸酮、2,4-二異丙基噻噸酮、2,4-二氯噻噸酮、1-氯-4-丙氧基噻噸酮等。
前述苯乙酮系化合物可舉例如:二乙氧基苯乙酮、2-羥基-2-甲基-1-苯基丙烷-1-酮、芐基二甲基縮酮、2-羥基-1-〔4-(2-羥基乙氧基)苯基〕-2-甲基丙烷-1-酮、1-羥基環己基苯基酮、2-甲基-1-(4-甲硫基苯基)-2-嗎啉基丙烷-1-酮、2-苄基-2-二甲基胺基-1-(4-嗎啉基苯基)丁烷-1-酮、2-(2-甲基苄基)-2-二甲基胺基-1-(4-嗎啉基苯基)-丁酮、2-(3-甲基苄基)-2-二甲基胺基-1-(4-嗎啉基苯基)-丁酮、2-(4-甲基苄基)-2-二甲基胺基-1-(4-嗎啉基苯基)-丁酮、2-(2-乙基苄基)-2-二甲基胺基-1-(4-嗎啉基苯基)-丁酮、2-(2-丙基苄基)-2-二甲基胺基-1-(4-嗎啉基苯基)-丁酮、2-(2-丁基苄基)-2-二甲基胺基-1-(4-嗎啉基苯基)-丁酮、2-(2,3-二甲基苄基)-2-二甲基胺基-1-(4-嗎啉基苯基)-丁酮、2-(2,4-二甲基苄基)-2-二甲基胺基-1-(4-嗎啉基苯基)-丁酮、2-(2-氯苄基)-2-二甲基胺基-1-(4-嗎啉基苯基)-丁酮、2-(2-溴苄基)-2-二甲基胺基-1-(4-嗎啉基苯基)-丁酮、2-(3-氯苄基)-2-二甲基胺基-1-(4-嗎啉基苯基)-丁酮、2-(4-氯苄基)-2-二甲基胺基-1-(4-嗎啉基苯基)-丁酮、2-(3-溴苄基)-2-二甲基胺基-1-(4-嗎啉基苯基)-丁酮、2-(4-溴苄基)-2-二甲基胺基-1-(4-嗎啉基苯基)-丁酮、2-(2-甲氧基苄基)-2-二甲基胺基-1-(4-嗎啉基苯基)-丁酮、2-(3-甲氧基苄基)-2-二甲基胺基-1-(4-嗎啉基苯基)-丁酮、2-(4-甲氧基苄基)-2-二甲基胺基-1-(4-嗎啉基苯基)-丁酮、2-(2-甲基-4-甲氧基苄基)-2-二甲基胺基-1-(4-嗎啉基苯基)-丁酮、2-(2-甲基-4-溴苄基)-2-二甲基胺基-1-(4-嗎啉基苯基)-丁酮、2-(2-溴-4-甲氧基苄基)-2-二甲基胺基-1-(4-嗎啉基苯基)-丁酮、2-羥基-2-甲基-1-〔4-(1-甲基乙烯基)苯基〕丙烷-1-酮之寡聚物等。
前述二咪唑化合物可舉例如:2,2’-雙(2-氯苯基)-4,4’,5,5’-四苯基二咪唑、2,2’-雙(2,3-二氯苯基)-4,4’,5,5’-四苯基二咪唑、2,2’-雙(2-氯苯基)-4,4’,5,5’-四苯基二咪唑、2,2’-雙(2-氯苯基)-4,4’,5,5’-四(烷氧基苯基)二咪唑、2,2’-雙(2-氯苯基)-4,4’,5,5’-四(二烷氧基苯基)二咪唑、2,2’-雙(2-氯苯基)-4,4’,5,5’-四(三烷氧基苯基)二咪唑、4,4’5,5’-位之苯基以羰烷氧基取代之咪唑化合物等。
前述三系化合物可舉例如:2,4-雙(三氯甲基)-6-(4-甲氧基苯基)-1,3,5-三、2,4-雙(三氯甲基)-6-(4-甲氧基萘基)-1,3,5-三、2,4-雙(三氯甲基)-6-胡椒基-1,3,5-三、2,4-雙(三氯甲基)-6-(4-甲氧基苯乙烯基)-1,3,5-三、2,4-雙(三氯甲基)-6-〔2-(5-甲基呋喃-2-基)乙烯基〕-1,3,5-三、2,4-雙(三氯甲基)-6-〔2-(呋喃-2-基)乙烯基〕-1,3,5-三、2,4-雙(三氯甲基)-6-〔2-(4-二乙胺基-2-甲基苯基)乙烯基〕-1,3,5-三、2,4-雙(三氯甲基)-6-〔2-(3,4-二甲氧基苯基)乙烯基〕-1,3,5-三等。
前述肟化合物可舉出:O-乙氧基羰基-α-氧亞胺基-1-苯基丙烷-1-酮等。
前述安息香系化合物可舉例如:安息香、安息香甲基醚、安息香乙基醚、安息香異丙基醚、安息香異丁基醚等。
前述二苯基酮系化合物可舉例如:二苯基酮、鄰苯甲醯基安息香酸甲酯、4-苯基二苯基酮、4-苯甲醯基-4’-甲基二苯基硫醚、3,3’,4,4’-四(過氧化第三丁基羰基)二苯基酮、2,4,6-三甲基二苯基酮等。
前述蒽系化合物可舉例如: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。
前述光陽離子聚合起始劑係藉由照射光產生酸,並開始感光性樹脂組成物所含有之光聚合性化合物之硬化反應(陽離子聚合)之化合物,包括吸收光的陽離子部及酸產生源之陰離子部。光陽離子聚合起始劑可單獨使用或組合2種以上使用。
光陽離子聚合起始劑之陰離子部可舉例如:[(Y)sB(Phf)4-s]-(式中,Y表示苯基或聯苯基,Phf表示至少1個氫原子經選自由全氟烷基、全氟烷氧基、及鹵原子之至少1種取代之苯基,s為0至3之整數)、BF4 -、[(Rf)kPF6-k]-(Rf:80%以上氫原子經氟原子取代之烷基,k:0至5之整數)、AsF6 -、SbF6 -、SbF5OH-等。
光陽離子聚合起始劑可舉例如:(4-羥基苯基)甲基苄基鋶四(五氟苯基)硼酸鹽、4-(4-聯苯基硫基)苯基-4-聯苯基苯基鋶四(五氟苯基)硼酸鹽、4-(苯基硫基)苯基二苯基鋶苯基三(五氟苯基)硼酸鹽、[4-(4-聯苯基硫基)苯基]-4-聯苯基苯基鋶苯基三(五氟苯基)硼酸鹽、二苯基[4-(苯基硫基)苯基]鋶三(五氟乙基)三氟磷酸酯、二苯基[4-(苯基硫基)苯基]鋶四(五氟苯基)硼酸鹽、二苯基[4-(苯基硫基)苯基]鋶六氟磷酸鹽、4-(4-聯苯基硫基)苯基-4-聯苯基苯基鋶三(五氟乙基)三氟磷酸酯、雙[4-(二苯基二氫硫基)苯基]硫化物苯基三(五氟苯基)硼酸鹽、[4-(2-噻噸酮基硫基)苯基]苯基-2-噻噸酮基鋶苯基三(五氟苯基)硼酸鹽、4-(苯基硫基)苯基二苯基鋶六氟銻酸酯等。
光陽離子聚合起始劑可使用:商品名「CYRACURE UVI-6970」、「CYRACURE UVI-6974」、「CYRACURE UVI-6990」、「CYRACURE UVI-950」(以上皆為美國Union Carbide公司製)、「Irgacure250」、「Irgacure261」、「Irgacure264」(以上皆為BASF公司製)、「CG-24-61」(Ciba-Geigy公司製)、「OPTOMER SP-150」、「OPTOMER SP-151」、「OPTOMER SP-170」、「OPTOMER SP-171」(以上皆為ADEKA股份有限公司製)、「DAICAT II」(Daicel股份有限公司製)、「UVAC1590」、「UVAC1591」(以上皆為Daicel-Cytec股份有限公司製)、「CI-2064」、「CI-2639」、「CI-2624」、「CI-2481」、「CI-2734」、「CI-2855」、「CI-2823」、「CI-2758」、「CIT-1682」(以上皆為日本曹達股份有限公司製)、「PI-2074」(Rhodia公司製四(五氟苯基)硼酸鹽甲苯甲基異丙苯基錪鹽)、「FFC509」(3M公司製)、「BBI-102」、「BBI-101」、「BBI-103」、「MPI-103」、「TPS-103」、「MDS-103」、「DTS-103」、「NAT-103」、「NDS-103」(以上皆為Midori Kagaku股份有限公司製)、「CD-1010」、「CD-1011」、「CD-1012」(以上皆為美國Sartomer公司製)、「CPI-100P」、「CPI-101A」(以上皆為san-apro股份有限公司製)等市售品。
相對於感光性樹脂組成物所含有光聚合性化合物(總量)100重量份,光聚合起始劑含量(含有2種以上時為其總量)較佳為例如0.1至100重量份,更佳為0.5至50重量份,又更佳為3至20重量份。光聚合起始劑含量低於上述範圍時,有硬化性降低之傾向。另一方面,光聚合起始劑含量高於上述範圍時,有硬化物容易著色之傾向。
<溶劑>
溶劑可舉例如:醚(二乙基醚;乙二醇單或二烷基醚、二乙二醇單或二烷基醚、丙二醇單或二烷基醚、丙二醇單或二芳基醚、二丙二醇單或二烷基醚、三丙二醇單或二烷基醚、1,3-丙二醇單或二烷基醚、1,3-丁二醇單或二烷基醚、1,4-丁二醇單或二烷基醚、甘油單或二或三烷基醚等二醇醚類等鏈狀醚;四氫呋喃、二噁烷等環狀醚等)、酯(乙酸甲酯、乙酸乙酯、乙酸丁酯、乙酸異戊酯、乳酸乙酯、3-甲氧基丙酸甲酯、3-乙氧基丙酸乙酯、C5-6環烷二醇單或二乙酸酯、C5-6環烷二甲醇單或二乙酸酯等羧酸酯類;乙二醇單烷基醚乙酸酯、乙二醇單或二乙酸酯、二乙二醇單烷基醚乙酸酯、二乙二醇單或二乙酸酯、丙二醇單烷基醚乙酸酯、丙二醇單或二乙酸酯、二丙二醇單烷基醚乙酸酯、二丙二醇單或二乙酸酯、1,3-丙二醇單烷基醚乙酸酯、1,3-丙二醇單或二乙酸酯、1,3-丁二醇單烷基醚乙酸酯、1,3-丁二醇單或二乙酸酯、1,4-丁二醇單烷基醚乙酸酯、1,4-丁二醇單或二乙酸酯、甘油單或二或三乙酸酯、甘油單或二C1-4烷基醚二或單乙酸酯、三丙二醇單烷基醚乙酸酯、三丙二醇單或二乙酸酯等二醇乙酸酯類或二醇醚乙酸酯類等)、酮(丙酮、甲基乙基酮、甲基異丁基酮、環己酮、3,5,5-三甲基-2-環己烯-1-酮等)等。該等溶劑可單獨使用或混合2種以上使用。
本揭示之感光性樹脂組成物除了上述成分以外例如可含有:酚醛清漆樹脂、苯酚樹脂、醯亞胺樹脂、含羧基之樹脂等樹脂;硬化劑、硬化促進劑、添加劑(填充劑、消泡劑、阻燃劑、抗氧化劑、紫外線吸收劑、著色劑、低應力化劑、可動性賦予劑、蠟類、樹脂、交聯劑、鹵素捕集劑、調平劑、濕性改良劑等)。
本揭示之感光性樹脂組成物中的鹼可溶性樹脂之濃度並無特別限定,例如可為2至60重量%,較佳為5至30重量%。
本揭示之感光性樹脂組成物之調製方法可舉例如於溶劑溶解鹼可溶性樹脂、光聚合性化合物、光聚合起始劑、及因應所需之其他添加劑之方法等。
本揭示之感光性樹脂組成物含有色材時,調製方法可舉例如於溶劑中因應所需並存顏料分散劑,使顏料等色材分散而調製色材分散液,另外將鹼可溶性樹脂、光聚合性化合物、光聚合起始劑、及因應所需之其他添加劑溶解於溶劑,將其與前述色材分散液混合,因應所需進一步添加溶劑之方法等。
本揭示之感光性樹脂組成物通常封入於容器而供於流通、保管。本揭示之感光性樹脂組成物在流通、保管時其保存穩定性優異。
<硬化物>
藉由硬化本揭示之感光性樹脂組成物而可得各物性優異之硬化物。例如,將上述感光性樹脂組成物以旋轉塗布器、浸漬塗布器、輥塗布器、狹縫塗布器等慣用塗布手段塗佈於各種基材或基板並形成塗膜後,硬化該塗膜,藉此可得硬化物。硬化係例如藉由對感光性樹脂組成物實施光照射及/或加熱處理而進行。
前述光照射例如使用:汞燈、氙燈、碳電弧燈、金屬鹵化物燈、太陽光、電子線源、雷射光源、LED光源等,較佳為以累積照射量例如成為500至5000mJ/cm2之範圍照射。
前述加熱處理例如較佳為以60至300℃(較佳為100至250℃)之溫度加熱例如1至120分鐘(較佳為1至60分鐘)加熱。
基材或基板可舉出:矽晶圓、金屬、塑膠、玻璃、陶瓷等。硬化後之塗膜之厚度例如較佳為0.05至20μm,更佳為0.1至10μm。
本揭示之硬化物(硬化後之塗膜)係耐溶劑性優異且具有高絕緣性者,故可利用為保護膜(彩色濾光片保護膜等)或絕緣膜、或微透鏡之形成材料等。
<彩色濾光片>
本揭示之彩色濾光片為本揭示之感光性樹脂組成物之硬化物。本揭示之彩色濾光片可為具備由前述感光性樹脂組成物形成之著色圖案者。彩色濾光片例如可經過於基板上使用前述感光性樹脂組成物形成著色圖案之步驟、及將前述著色圖案進行後烤之步驟而製造。
使用本揭示之感光性樹脂組成物形成彩色濾光片之圖案之方法可舉例如:將本揭示之感光性樹脂組成物以旋轉塗布器等慣用塗布手段塗布於基板或其他樹脂層上,去除溶劑等揮發成分並形成著色層,透過光罩曝光該著色層而顯影之方法等。
基板可舉例如:玻璃基板、聚矽氧基板、聚碳酸酯基板、聚酯基板、芳香族聚醯胺基板、聚醯胺醯亞胺基板、聚醯亞胺基板、Al基板、GaAs基板等表面平坦之基板等。該等基板可實施利用矽烷耦合劑等藥品進行之藥品處理、電漿處理、離子電鍍處理、濺鍍處理、氣相反應處理、真空蒸鍍處理等前處理。
乾燥後之著色層之厚度例如為0.6至8μm,較佳為1至5μm。
曝光時所使用之放射線之光源可舉例如:氙燈、鹵素燈、鎢燈、高壓汞燈、超高壓汞燈、金屬鹵化物燈、中壓汞燈、低壓汞燈等燈光源或氬離子雷射、YAG雷射、XeCl準分子雷射、氮雷射等雷射光源等。放射線之波長較佳為190至450nm之範圍。放射線之曝光量一般較佳為10至10,000J/m2。
顯影所使用之鹼顯影液較佳為例如:碳酸鈉、氫氧化鈉、氫氧化鉀、四甲基氫氧化銨、膽鹼、1,8-二氮雜雙環-[5.4.0]-7-十一烯、1,5-二氮雜雙環-[4.3.0]-5-壬烯等水溶液。
後烤之條件通常為120至280℃、10至60分鐘左右。如此施行而形成之像素的膜厚通常為0.5至5μm,較佳為1至3μm。
根據本揭示之感光性樹脂組成物可獲得硬化反應性優異且具有充分耐溶劑性之著色圖案。
<顯示裝置用構件或顯示裝置>
本揭示之顯示裝置用構件或顯示裝置係具備前述彩色濾光片。前述顯示裝置用構件可舉例如彩色液晶顯示元件。又,前述顯示裝置可舉例如彩色液晶顯示裝置。彩色液晶顯示元件或彩色液晶顯示之構造無特別限定,可為適當構造。
此外,本說明書所揭示之各態樣可組合本說明書所揭示之其他任何特徵。又,各實施型態中的各構成及該等的組合等僅為一例,可在不超出本發明主旨之範圍內適當地進行構成之附加、省略、及其他變更。本揭示不限定於實施型態,而以申請專利範圍為準。
(實施例)
以下,根據實施例進一步具體地說明本揭示。
共聚物之重量平均分子量(聚苯乙烯換算)及分散度(重量平均分子量Mw/數平均分子量Mn)是用以下條件測定。
裝置:檢測器:RID-20A(島津製作所)。
泵:LC-20AD(島津製作所)。
系統控制器:CBM-20Alite(島津製作所)。
脫氣器:DGU-20A3(島津製作所)。
自動注射器:SIL-20A HT(島津製作所)。
管柱:Shodex KF-806L(昭和電工)。
溶析液:THF(四氫呋喃)0.8ml/min。
溫度:烘箱:40℃、RI:40℃。
檢測器:RI。
發熱峰頂溫度是用以下方法測定。亦即,將製造例1至8所得之含共聚物的溶液5g於50g庚烷中一邊攪拌一邊滴入。過濾所產生之沉殿物,減壓乾燥,藉此獲得白色粉末之共聚物。將前述白色粉末之約10mg作為樣品,使用示差掃描熱量計(METTLER TOLEDO公司製DSC1)在氮氣環境下,從40℃以5℃/分鐘之速度升溫至300℃,測定發熱峰頂溫度。
[參考例1/單體B1之製作]
對於添加有33.7g之5-降莰烯-2-甲醇、41.3g之三乙胺、及6.5mg之對苯二酚單甲醚57.2g之THF(四氫呋喃)之混合溶液,將42.4g之甲基丙烯酸氯化物一邊將內溫維持於20℃以下一邊花費40分鐘滴入後,於20℃攪拌4小時。以氣相層析法確認屬於原料之5-降莰烯-2-甲醇消失後,添加
100g之乙酸醚及84.0g之水。分液後以94.8g之10%氫氧化鈉水溶液洗淨,以68.0g之水洗淨3次。將所得之有機相以40℃、15Torr之條件濃縮,藉此獲得48.3g之5-降莰烯-2-甲基丙烯酸酯粗生成物。前述粗生成物之純度為93%,產率為86%。
對於添加有47.5g之前述5-降莰烯-2-甲基丙烯酸酯粗生成物及9.4mg之對苯二酚單甲醚141g之乙酸乙酯之混合溶液,將72.3g之mCPBA(3-氯過氧安息香酸,30%含水)一邊將內溫維持於20℃以下一邊花費1小時添加後,於20℃攪拌3小時。以氣相層析法確認原料消失後,添加278g之15%硫代硫酸鈉水溶液及141g之乙酸醚並攪拌15分鐘。分液後以217g之8%碳酸氫鈉水溶液洗淨,以141g之水洗淨2次。濃縮有機相後,以氧化矽凝膠管柱層析法精製,藉此獲得29.4g之3-氧雜三環[3.2.1.02,4]辛烷-6-基甲基丙烯酸甲酯(以下稱為「單體B1」)。3-氧雜三環[3.2.1.02,4]辛烷-6-基甲基丙烯酸甲酯之純度為99%,產率為71%。
[製造例1]
於具備迴流冷卻器、滴液漏斗、及攪拌機之1L之燒瓶內適當地流通氮並形成氮環境,於前述燒瓶內添加150重量份之丙二醇單甲基醚乙酸酯,一邊攪拌一邊加熱至80℃。其後,將7重量份之2,2’-偶氮雙異丁腈(AIBN)一邊使用30重量份之丙二醇單甲基醚乙酸酯洗流一邊添加。接著,於該燒瓶內使用滴入泵花費約4小時滴入作為單體之11重量份之丙烯酸(AA)及89重量份之單體B1與20重量份之丙二醇單甲基醚乙酸酯的混合溶液。單體滴入結束後,於同溫度保持4小時,其後冷卻至室溫,而得固形份34.6
重量%之含共聚物溶液。所生成之共聚物之重量平均分子量Mw為19,000,分散度為3.47。
[製造例2]
除了使用作為單體之11重量份之丙烯酸(AA)、79重量份之單體B1、及10重量份之苯乙烯(ST)以外,其餘與製造例1進行相同之操作,藉此獲得固形份33.8重量%之含共聚物的溶液。所生成之共聚物之重量平均分子量Mw為17,000,分散度為3.33。
[製造例3]
除了使用作為單體之11重量份之丙烯酸(AA)、79重量份之單體B1、及10重量份之甲基丙烯酸甲酯(MMA)以外,其餘與製造例1進行相同之操作,藉此獲得固形份34.2重量%之含共聚物的溶液。所生成之共聚物之重量平均分子量Mw為18,500,分散度為3.41。
[製造例4]
除了使用作為單體之11重量份之丙烯酸(AA)、79重量份之單體B1、及10重量份之環己基順丁烯二醯亞胺(CHMI)以外,其餘與製造例1進行相同之操作,藉此獲得固形份34.4重量%之含共聚物的溶液。所生成之共聚物之重量平均分子量Mw為18,000,分散度為3.40。
[製造例5]
除了使用作為單體之11重量份之丙烯酸(AA)、79重量份之單體B1、及10重量份之N-乙烯基吡咯啶酮(VP)以外,其餘與製造例1進行相同之操作,藉此獲得固形份34.4重量%之含共聚物的溶液。所生成之共聚物之重量平均分子量Mw為17,500,分散度為3.38。
[製造例6]
於具備迴流冷卻器、滴液漏斗及攪拌機之1L燒瓶內適當流通氮並形成氮環境,添加150重量份之丙二醇單甲基醚乙酸酯,一邊攪拌一邊加熱至65℃。其後將14重量份之2,2’-偶氮雙(2,4-二甲基戊腈)一邊以30重量份之丙二醇單甲基醚乙酸酯洗流一邊添加。接著,於該燒瓶內使用滴入泵花費約4小時滴入於20重量份之丙二醇單甲基醚乙酸酯中溶解有作為單體之11重量份之丙烯酸(AA)、79重量份之甲基丙烯酸環氧丙酯(GMA)、10重量份之甲基丙烯酸甲酯(MMA)之溶液。單體滴入結束後,於同溫度保持約4小時,其後冷卻至室溫,而得固形份33.8重量%之含共聚物的溶液。所生成之共聚物之重量平均分子量Mw為16,000,分散度為3.32。
[製造例7]
除了使用作為單體之11重量份之丙烯酸(AA)、79重量份之甲基丙烯酸3,4-環氧環己基甲酯(cyclomer M100)、10重量份之甲基丙烯酸甲酯(MMA)以外,其餘與製造例6進行相同之操作,而得固形份33.4重量%之含共聚物的溶液。所生成之共聚物之重量平均分子量Mw為16,000,分散度為3.30。
[製造例8]
除了使用作為單體之11重量份之丙烯酸(AA)、89重量份之丙烯酸3,4-環氧基三環[5.2.1.02,6]癸烷-9-基酯與丙烯酸3,4-環氧基三環[5.2.1.02,6]癸烷-8-基酯之混合物(單體B2)以外,其餘與製造例1進行相同之操作,而得固形份34.1重量%之含共聚物的溶液。所生成之共聚物之重量平均分子量Mw為18,000,分散度為3.43。
製造例1至8中的共聚物組成、共聚物之重量平均分子量、分散度及發熱峰頂溫度示於表1。
[實施例1-1]
於容器分別量取作為鹼可溶性樹脂之上述製造例1所得之共聚物作成的含共聚物的溶液之8.09g、作為光聚合性化合物之DPHA2.25g、作為光聚合起始劑之1-羥基環己苯基酮0.20g、作為溶劑之MMPGAC6.83g,藉由攪拌30分鐘而調製出感光性樹脂組成物1-1。
[實施例1-2]
除了使用作為鹼可溶性樹脂之上述製造例2所得之共聚物作成的含共聚物的溶液8.09g以外,其餘與實施例1-1進行相同之操作而調製出感光性樹脂組成物1-2。
[實施例1-3]
除了使用作為鹼可溶性樹脂之上述製造例3所得之共聚物作成的含共聚物的溶液8.09g以外,其餘與實施例1-1進行相同之操作而調製出感光性樹脂組成物1-3。
[實施例1-4]
除了使用作為鹼可溶性樹脂之上述製造例4所得之共聚物作成的含共聚物的溶液8.09g以外,其餘與實施例1-1進行相同之操作而調製出感光性樹脂組成物1-4。
[實施例1-5]
除了使用作為鹼可溶性樹脂之上述製造例5所得之共聚物作成的含共聚物的溶液8.09g以外,其餘與實施例1-1進行相同之操作而調製出感光性樹脂組成物1-5。
[比較例1-1]
除了使用作為鹼可溶性樹脂之上述製造例6所得之共聚物作成的含共聚物的溶液8.09g以外,其餘與實施例1-1進行相同之操作而調製出感光性樹脂組成物1-6。
[比較例1-2]
除了使用作為鹼可溶性樹脂之上述製造例7所得之共聚物作成的含共聚物的溶液8.09g以外,其餘與實施例1-1進行相同之操作而調製出感光性樹脂組成物1-7。
[比較例1-3]
除了使用作為鹼可溶性樹脂之上述製造例8所得之共聚物作成的含共聚物的溶液8.09g以外,其餘與實施例1-1進行相同之操作而調製出感光性樹脂組成物1-8。
表2記載上述實施例及比較例之感光性樹脂組成物之組成。
[實施例2-1]
於容器中分別量取作為色材之顏料之C.I.顏料紅254 7.7g、作為分散劑之DISPERBYK-2000 3.1g、作為溶劑之MMPGAC 36.0g,進一步添加直徑1.0mm之二氧化鋯珠45g並加蓋。將其以油漆攪拌器(Paint shaker)震盪3小時,3小時後分離顏料分散液及二氧化鋯珠,添加0.5mm之二氧化鋯珠45g並以油漆攪拌器進一步震盪3小時。其後分離顏料分散液及二
氧化鋯珠,添加0.3mm之二氧化鋯珠45g並以油漆攪拌器進一步震盪3小時後,分離二氧化鋯珠,而得顏料分散液。
對於所得之顏料分散液4.68g,於容器分別量取作為鹼可溶性樹脂之上述製造例1所得之共聚物作成的含共聚物的溶液8.09g、作為光聚合性化合物之DPHA 2.25g、作為光聚合起始劑之1-羥基環己苯基酮0.20g、作為溶劑之MMPGAC 15.2g,攪拌30分鐘,藉此調製出感光性樹脂組成物2-1。
[實施例2-2]
除了使用作為鹼可溶性樹脂之上述製造例2所得之共聚物作成的含共聚物的溶液8.09g以外,其餘與實施例2-1進行相同之操作而調製出感光性樹脂組成物2-2。
[實施例2-3]
除了使用作為鹼可溶性樹脂之上述製造例3所得之共聚物作成的含共聚物的溶液8.09g以外,其餘與實施例2-1進行相同之操作而調製出感光性樹脂組成物2-3。
[實施例2-4]
除了使用作為鹼可溶性樹脂之上述製造例4所得之共聚物作成的含共聚物的溶液8.09g以外,其餘與實施例2-1進行相同之操作而調製出感光性樹脂組成物2-4。
[實施例2-5]
除了使用作為鹼可溶性樹脂之上述製造例5所得之共聚物作成的含共聚物的溶液8.09g以外,其餘與實施例2-1進行相同之操作而調製出感光性樹脂組成物2-5。
[比較例2-1]
除了使用作為鹼可溶性樹脂之上述製造例6所得之共聚物作成的含共聚物的溶液8.09g以外,其餘與實施例2-1進行相同之操作而調製出感光性樹脂組成物2-6。
[比較例2-2]
除了使用作為鹼可溶性樹脂之上述製造例7所得之共聚物作成的含共聚物的溶液8.09g以外,其餘與實施例2-1進行相同之操作而調製出感光性樹脂組成物2-7。
[比較例2-3]
除了使用作為鹼可溶性樹脂之上述製造例8所得之共聚物作成的含共聚物的溶液8.09g以外,其餘與實施例2-1進行相同之操作而調製出感光性樹脂組成物2-8。
表4記載上述實施例及比較例之感光性樹脂組成物之組成。
<評估試驗>
使用實施例1-1至1-5及比較例1-1至1-3所得之各感光性樹脂組成物進行下列評估試驗。結果示於表3。
(1)保存穩定性試驗-1
將實施例1-1至1-5及比較例1-1至1-3所得之感光性樹脂組成物於40℃之烘箱保管1週。測定聚合後之黏度及於40℃保管1週後之黏度。利
用下式計算出黏度增加率。此外,黏度(單元:mPa.s)係使用黏度計(商品名「LVDV2T」,Brookfield公司製)在旋轉數60、溫度:23℃之條件下測定。
P:聚合後之黏度,Q:於40℃保管1週後之黏度。
黏度增加率={(Q/P)×100}-100。
(2)耐溶劑性試驗-1
將實施例1-1至1-5及比較例1-1至1-3所得之感光性樹脂組成物以旋轉塗布器塗布於玻璃板後,以200℃加熱硬化30分鐘,藉此製作出試驗片。硬化後之塗膜之厚度為3μm。
對於試驗片分別滴入1滴γ-丁內酯(γ-BL)及N-甲基吡咯啶酮(NMP),放置10分鐘。其後水洗,滴入溶劑處完全無變化為◎,稍微殘留溶劑痕跡但擦拭後消失為○,殘留溶劑痕跡且擦拭也無法消去為△,整面變色為×。
(3)耐溶劑性試驗-2
在試驗片之調製中除了硬化溫度設為230℃以外,其餘與耐溶劑性試驗-1相同地施作進行硬化物之耐溶劑性試驗。
實施例1-1至1-5之感光性樹脂組成物即使在40℃也不易增黏,保存穩定性良好。又,硬化溫度即使為200℃亦與230℃時同樣地顯示良好的耐溶劑性。另一方面,比較例1-1至1-2之感光性樹脂組成物在40℃會凝膠化,由此可知保存穩定性較差。又,比較例3之感光性樹脂組成物係藉由使用單體B2(EDCPA)而保存穩定性良好,但硬化溫度若從230℃降低至200℃則無法充分地硬化,故可知耐溶劑性降低。
接著,使用實施例2-1至2-5及比較例2-1至2-3所得之各感光性樹脂組成物進行下列評估試驗。結果示於表5。
(1)保存穩定性試驗-2
將實施例2-1至2-5及比較例2-1至2-3所得之感光性樹脂組成物於40℃之烘箱保管1週。測定聚合後之黏度及於40℃保管1週後之黏度。利用下式計算出黏度增加率。此外,黏度(單元:mPa.s)係使用黏度計(商品名「LVDV2T」,Brookfield公司製)在旋轉數60、溫度:23℃之條件測定。
P:聚合後之黏度,Q:於40℃保管1週後之黏度。
黏度增加率={(Q/P)×100}-100。
(2)耐溶劑性試驗-3
將實施例2-1至2-5及比較例2-1至2-3所得之感光性樹脂組成物以旋轉塗布器塗布於玻璃板後,以200℃加熱硬化30分鐘,藉此製作出試驗片。硬化後之塗膜之厚度為2μm。
對於試驗片分別滴入1滴γ-丁內酯(γ-BL)及N-甲基吡咯啶酮(NMP),放置10分鐘。其後水洗,滴入溶劑處完全無變化為◎,稍微殘留溶劑痕跡但擦拭後消失為○,殘留溶劑痕跡且擦拭也無法消去為△,整面變色為×。
(3)耐溶劑性試驗-4
在試驗片之調製中除了硬化溫度設為230℃以外,其餘與耐溶劑性試驗-3相同地施作進行硬化物之耐溶劑性試驗。
實施例2-1至2-5之感光性樹脂組成物即使在40℃也不易增黏,保存穩定性良好。又,硬化溫度即使為200℃亦與230℃時同樣地顯
示良好的耐溶劑性。另一方面,比較例2-1至2-2之感光性樹脂組成物在40℃會增黏,由此可知保存穩定性較差。又,比較例2-3之感光性樹脂組成物係藉由使用單體B2(EDCPA)而保存穩定性良好,但硬化溫度若從230℃降低至200℃則無法充分地硬化,故可知耐溶劑性降低。
以下,說明製造例、實施例及比較例所使用之成分。
單體B1:3-氧雜三環[3.2.1.02,4]辛烷-6-基甲基丙烯酸甲酯(參照參考例1)。
GMA:甲基丙烯酸環氧丙酯(日油股份有限公司製)。
cyclomer M100:甲基丙烯酸3,4-環氧基環己基甲酯(Daicel股份有限公司製)。
單體B2:丙烯酸3,4-環氧基三環[5.2.1.02,6]癸烷-9-基酯與丙烯酸3,4-環氧基三環[5.2.1.02,6]癸烷-8-基酯之混合物(商品名「E-DCPA」,Daicel股份有限公司製)。
ST:苯乙烯(FUJIFILM和光純藥股份有限公司製)。
MMA:甲基丙烯酸甲酯(FUJIFILM和光純藥股份有限公司製)。
CHMI:環己基順丁烯二醯亞胺(日本觸媒股份有限公司製)。
VP:N-乙烯基吡咯啶酮(東京化成工業股份有限公司製)。
MMPGAC:丙二醇單甲基醚乙酸酯(Daicel股份有限公司製)。
PR 254:C.I.顏料紅254(東京化成工業股份有限公司製)。
DISPERBYK-2000:胺價4mgKOH/g,非揮發份40%(BYK JAPAN製)。
DHPA:二新戊四醇六丙烯酸酯(商品名「KAYARAD DPHA」;日本化藥股份有限公司製)。
1-羥基環己苯基酮(FUJIFILM和光純藥股份有限公司製)。
綜上所述,以下附註本發明之構成及其變化。
[1]一種感光性樹脂組成物,係含有鹼可溶性樹脂、光聚合性化合物、光聚合起始劑、及溶劑,其中,
該鹼可溶性樹脂係含有源自於不飽和羧酸或其酐之構成單元(A)及源自於前述式(1)所示化合物的構成單元(B),且使用示差掃描熱量計以5℃/分鐘之速度升溫時所顯示發熱峰頂溫度為180至220℃的共聚物,
(式中,R1及R2分別相同或相異地表示氫原子或碳數1至7之烷基,X表示單鍵或可含有雜原子之2價烴基,Y表示可具有碳數1至3之烷基作為取代基之亞甲基或伸乙基、氧原子、或可與氧原子鍵結之硫原子,n表示0至7之整數)。
[2]如[1]所述之感光性樹脂組成物,其中,前述式(1)所示化合物為前述式(1a)所示之化合物
(式中,R1、R2、X、Y、及n同式(1)所說明)。
[3]如[1]或[2]所述之感光性樹脂組成物,其中,前述共聚物更含有源自選自於下述(c1)至(c4)所成群組中之至少1種化合物之構成單元(C),
(c1)可經烷基取代之苯乙烯;
(c2)N-取代順丁烯二醯亞胺;
(c3)N-乙烯基化合物;
(c4)前述式(2)所示之不飽和羧酸衍生物;
(式中,R11表示氫原子或碳數1至7之烷基。R12表示可含有雜原子之烴基。Z表示雜原子。)
[4]如[1]至[3]中任一項所述之感光性樹脂組成物,其中,前述共聚物更含有構成單元(D),該構成單元(D)係源自於(甲基)丙烯醯胺或(甲基)丙烯腈之構成單元。
[5]如[1]至[4]中任一項所述之感光性樹脂組成物,其中,相對於前述共聚物之全構成單元,構成單元(A)之比例為2至60重量%、3至40重量%、或5至20重量%。
[6]如[1]至[5]中任一項所述之感光性樹脂組成物,其中,相對於前述共聚物之全構成單元,構成單元(B)之比例為40至98重量%、60至95重量%、或75至90重量%。
[7]如[3]、[5]、及[6]中任一項所述之感光性樹脂組成物,其中,相對於前述共聚物之全構成單元,構成單元(C)之比例為0至85重量%、1至60重量%、2至40重量%。
[8]如[3]、[5]至[7]中任一項所述之感光性樹脂組成物,其中,相對於前述共聚物之全構成單元,構成單元(A)之比例為2至60重量%,構成單元(B)含量為40至98重量%,構成單元(C)含量為0至85重量%。
[9]如[1]至[8]中任一項所述之感光性樹脂組成物,其中,前述共聚物含有構成單元(A)及構成單元(B)且不含有構成單元(C)時,相對於全構成單元,構成單元(A)及構成單元(B)的總量為90重量%以上、95重量%以上、99重量%以上、或實質上為100重量%,前述共聚物含有構成單元(A)、構成單元(B)及構成單元(C)時,相對於全構成單元,構成單元(A)至(C)之總量為90重量%以上、95重量%以上、99重量%以上、或100重量%。
[10]如[1]至[9]中任一項所述之感光性樹脂組成物,其中,前述共聚物之重量平均分子量(Mw)為1000至1000000、3000至300000、或5000至100000。
[11]如[1]至[10]中任一項所述之感光性樹脂組成物,其中,前述共聚物之分子量分佈(重量平均分子量與數平均分子量的比:Mw/Mn)為5.0以下、1.0至4.5、或1.0至4.0。
[12]如[1]至[11]中任一項所述之感光性樹脂組成物,其中,前述聚合物使用示差掃描熱量計以5℃/分鐘之速度升溫時所顯示發熱峰頂溫度為180至220℃。
[13]如[1]至[12]中任一項所述之感光性樹脂組成物,係更含有色材。
[14]如[13]所述之感光性樹脂組成物,其中,前述色材為顏料及/或染料。
[15]如[13]或[14]所述之感光性樹脂組成物,其中,相對於感光性樹脂組成物之固形份,色材含量為3至50重量%、5至30重量%。
[16]如[1]至[15]中任一項所述之感光性樹脂組成物,其中,前述光聚合性化合物含有選自由多官能乙烯基化合物、多官能硫醇化合物、及多官能環氧化合物所成群組中之至少1種。
[17]如[1]至[16]中任一項所述之感光性樹脂組成物,其中,相對於鹼可溶性樹脂100重量份,光聚合性化合物含量為10至300重量份、30至200重量份、或40至150重量份,感光性樹脂組成物含有色材時,相對於色材100重量份,光聚合性化合物含量為10至1000重量份、50至600重量份、或100至500重量份。
[18]一種[1]至[17]中任一項所述之感光性樹脂組成物之硬化物。
[19]一種彩色濾光片,係[1]至[17]中任一項所述之感光性樹脂組成物之硬化物。
[20]一種顯示裝置用構件或顯示裝置,係具備[19]所述之彩色濾光片。
(產業上之可利用性)
根據本揭示之發明可提供一種保存穩定性優異、硬化反應性優異、且硬化物之耐溶劑性優異之感光性樹脂組成物。又,可提供一種具有上述特性之感光性樹脂組成物之硬化物、該硬化物之彩色濾光片、及具備該彩色濾光片之顯示裝置用構件或顯示裝置。
Claims (8)
- 如請求項2所述之感光性樹脂組成物,其中,相對於前述共聚物之全構成單元,前述構成單元(A)之比例為2至60重量%,前述構成單元(B)之比例為40至98重量%,前述構成單元(C)之比例為0至85重量%。
- 如請求項1至3中任一項所述之感光性樹脂組成物,係更含有色材。
- 如請求項4所述之感光性樹脂組成物,其中,前述色材為顏料及/或染料。
- 一種請求項1至5中任一項所述之感光性樹脂組成物之硬化物。
- 一種彩色濾光片,係請求項1至5中任一項所述之感光性樹脂組成物之硬化物。
- 一種顯示裝置用構件或顯示裝置,係具備請求項7所述之彩色濾光片。
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JP2020039965A JP7483417B2 (ja) | 2020-03-09 | 感光性樹脂組成物、及びその硬化物 | |
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JPH09134004A (ja) | 1995-11-07 | 1997-05-20 | Sumitomo Chem Co Ltd | 着色レジスト組成物およびその製造方法 |
JP3022412B2 (ja) * | 1997-06-19 | 2000-03-21 | 日本電気株式会社 | ネガ型フォトレジスト材料、およびそれを用いたパターン形成方法 |
JPH11133600A (ja) | 1997-10-30 | 1999-05-21 | Jsr Corp | 表示パネルスペーサー用感放射線性樹脂組成物 |
JP4501665B2 (ja) | 2004-12-14 | 2010-07-14 | 住友化学株式会社 | 感光性樹脂組成物 |
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