TW201800841A - 黑色感光性樹脂組合物及自其製備之黑色管柱狀間隔物 - Google Patents
黑色感光性樹脂組合物及自其製備之黑色管柱狀間隔物 Download PDFInfo
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- TW201800841A TW201800841A TW106101047A TW106101047A TW201800841A TW 201800841 A TW201800841 A TW 201800841A TW 106101047 A TW106101047 A TW 106101047A TW 106101047 A TW106101047 A TW 106101047A TW 201800841 A TW201800841 A TW 201800841A
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- black
- resin composition
- photosensitive resin
- meth
- acrylate
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- 239000011342 resin composition Substances 0.000 title claims abstract description 76
- 125000006850 spacer group Chemical group 0.000 title abstract description 33
- 230000003287 optical effect Effects 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims description 77
- 229920001577 copolymer Polymers 0.000 claims description 39
- 239000003086 colorant Substances 0.000 claims description 36
- 239000007787 solid Substances 0.000 claims description 29
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- 229920000647 polyepoxide Polymers 0.000 claims description 25
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- 229920006243 acrylic copolymer Polymers 0.000 claims description 12
- 239000000178 monomer Substances 0.000 claims description 10
- 125000003700 epoxy group Chemical group 0.000 claims description 9
- 229920001519 homopolymer Polymers 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 238000004040 coloring Methods 0.000 claims 1
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- 230000015572 biosynthetic process Effects 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 102
- -1 acrylfluorenyl Chemical group 0.000 description 84
- 239000002904 solvent Substances 0.000 description 33
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 27
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- 239000000203 mixture Substances 0.000 description 24
- 238000002360 preparation method Methods 0.000 description 22
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
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- 238000011161 development Methods 0.000 description 7
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- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 6
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- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
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Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- General Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Structural Engineering (AREA)
- Architecture (AREA)
- Engineering & Computer Science (AREA)
- Materials For Photolithography (AREA)
- Optical Filters (AREA)
- Polymerisation Methods In General (AREA)
- Liquid Crystal (AREA)
Abstract
本文揭示一種黑色感光性樹脂組合物及自其製備之黑色管柱狀間隔物。所述黑色感光性樹脂組合物可形成呈現針對基板之良好黏著性、良好高度差特性、良好表面粗糙度及高光屏蔽特性(光密度)的固化膜,且可有效用於形成液晶顯示器(LCD)或有機發光二極體(OLED)顯示器之固化膜,特別是黑色管柱狀間隔物。
Description
本發明係關於一種黑色感光性樹脂組合物及自其製備之黑色管柱狀間隔物,詳言之一種黑色感光性樹脂組合物,其適合作為形成用於液晶顯示器(LCD)或有機發光二極體(OLED)顯示器之面板的間隔物、光屏蔽部件等的材料,以及一種固化膜,特別是自其製備之黑色管柱狀間隔物(BCS)。
最近,在LCD之液晶單元中採用使用感光性樹脂組合物所形成之間隔物以維持上部與下部透明基板之間的恆定距離。LCD為一種藉由向注入至兩個透明基板之間的恆定間隙中之液晶材料施加電壓而驅動的電光裝置,在LCD中非常關鍵的是維持兩個基板之間的間隙不變。若透明基板之間的間隙不恆定,則向其施加之電壓以及穿透此區域之光的透射率可發生改變,導致空間不均勻亮度之缺陷。根據最近對大尺寸LCD面板的需求,維持兩個透明基板之間的恆定間隙甚至愈加關鍵。
間隔物可藉由以下形成:將感光性樹脂組合物塗佈於基板上,且使用光罩將經塗佈之基板曝露於紫外光等,
隨後使其顯影。最近,已致力於將光屏蔽材料用於間隔物;因此,已積極研發各種有色感光性樹脂組合物。
就此而言,已揭示用於形成黑色管柱狀間隔物之各種黑色感光性樹脂組合物(參見日本早期公開公開案第2001-154206號、朝鮮專利第10-0814660號及朝鮮早期公開公開案第2000-0035753號)。
為了賦予高光屏蔽特性,需要提高添加至樹脂組合物中之顏料的含量。然而,在此情況下,可形成具有退化的針對基板之黏著性、表面粗糙度及高度差特性的固化膜。朝鮮專利第10-0814660號揭示一種使用具有良好光屏蔽特性及低介電常數之黑色有機顏料的方法。然而,當使用黑色有機顏料時,相較於碳黑,需要大量黑色有機顏料以實現高光密度。
因此,迫切需要針對黑色感光性樹脂組合物之研究,所述黑色感光性樹脂組合物滿足LCD或OLED顯示器中固化膜之所有特性,其包含黏著性、高度差特性、表面粗糙度及光屏蔽特性,在具有高度差之黑色管柱狀間隔物中尤其需要所述特性。
本發明之目標為提供一種黑色感光性樹脂組合物以及自其製備之固化膜,所述黑色感光性樹脂組合物可產生滿足良好黏著性、表面粗糙度及高光屏蔽特性(光密度)之固化膜,特別是具有良好高度差特性之黑色管柱狀間隔物。
根據本發明之一個態樣,提供一種黑色感光性樹脂組合物,其包括(A)丙烯酸共聚物;(B)環氧樹脂或自其衍生之化合物;(C)不同於(A)及(B)之環氧化合物;(D)光可聚合化合物;(E)光引發劑;及(F)黑色著色劑。
本發明之黑色感光性樹脂組合物可形成呈現良好黏著性、良好高度差特性、良好表面粗糙度及高光屏蔽特性(光密度)之固化膜,且可有效用於形成固化膜,特別是液晶顯示器(LCD)或有機發光二極體(OLED)顯示器之黑色管柱狀間隔物。
圖1為示出形成於實驗實例1中之主管柱狀間隔物(主CS)及子管柱狀間隔物(子CS)的各自形狀及高度差(分級)之示意圖。
圖2為示出用於實驗實例1中之100%全色調(F/T)管柱狀間隔物圖案光罩及30%半色調(H/T)管柱狀間隔物圖案光罩中之每一者的示意圖。
根據本發明之黑色感光性樹脂組合物可包括(A)丙烯酸共聚物;(B)環氧樹脂或自其衍生之化合物;(C)不同於(A)及(B)之環氧化合物;(D)光可聚合化合物;(E)光引發劑;及(F)黑色著色劑,且可進一步包括(G)溶劑,及(H)界面活性劑及/或(I)視需要作為添加劑之矽烷偶合
劑。
在下文中,將詳細解釋本發明之構成組分。
在本發明中,(甲基)丙烯醯基意指丙烯醯基及/或甲基丙烯醯基,且(甲基)丙烯酸酯意指丙烯酸酯及/或甲基丙烯酸酯。
(A)丙烯酸共聚物
本發明之黑色感光性樹脂組合物可包含丙烯酸共聚物,其可為無規共聚物。
本發明之共聚物包含(A-1)衍生自烯系不飽和羧酸、烯系不飽和羧酸酐或其組合之結構單元及(A-2)衍生自含有芳環之烯系不飽和化合物的結構單元,且可額外包含(A-3)衍生自不同於結構單元(A-1)及(A-2)之烯系不飽和化合物的結構單元。
共聚物為用於在顯影步驟期間達成所要顯影性之鹼溶性樹脂,且可同時充當用於在塗佈後形成膜之基礎載體及用於實現最終圖案之結構。
(A-1)衍生自烯系不飽和羧酸、烯系不飽和羧酸酐或其組合之結構單元
在本發明中,結構單元(A-1)係衍生自烯系不飽和羧酸、烯系不飽和羧酸酐或其組合。烯系不飽和羧酸或烯系不飽和羧酸酐為分子中具有至少一個羧基之可聚合不飽和單體。
烯系不飽和羧酸及烯系不飽和羧酸酐之特定實例可包含不飽和單羧酸,諸如(甲基)丙烯酸、丁烯酸、α-氯丙烯酸及肉桂酸;不飽和二羧酸及其酸酐,諸如順丁烯二酸、
順丁烯二酸酐、反丁烯二酸、衣康酸、衣康酸酐、檸康酸、檸康酸酐及甲基反丁烯二酸;三價或更高之不飽和聚羧酸及其酸酐;及二價或更高之聚羧酸的單[(甲基)丙烯醯氧基烷基]酯,諸如單[2-(甲基)丙烯醯氧基乙基]丁二酸酯及單[2-(甲基)丙烯醯氧基乙基]鄰苯二甲酸酯。
衍生自上文所例示之化合物的結構單元可單獨或以其兩者或更多者之組合形式包含於共聚物中。
以構成共聚物之結構單元的總莫耳數計,結構單元(A-1)之量可為5至65莫耳%,較佳為10至50莫耳%,以輕易地維持顯影性。
(A-2)衍生自含有芳環之烯系不飽和化合物的結構單元
在本發明中,結構單元(A-2)係衍生自含有芳環之烯系不飽和化合物。
含有芳環之烯系不飽和化合物的特定實例可包含(甲基)丙烯酸苯酯、(甲基)丙烯酸苄酯、(甲基)丙烯酸2-苯氧基乙酯、苯氧基二乙二醇(甲基)丙烯酸酯、對壬基苯氧基聚乙二醇(甲基)丙烯酸酯、對壬基苯氧基聚丙二醇(甲基)丙烯酸酯、(甲基)丙烯酸三溴苯酯;苯乙烯;含有烷基取代基之苯乙烯,諸如甲基苯乙烯、二甲基苯乙烯、三甲基苯乙烯、乙基苯乙烯、二乙基苯乙烯、三乙基苯乙烯、丙基苯乙烯、丁基苯乙烯、己基苯乙烯、庚基苯乙烯及辛基苯乙烯;具有鹵素之苯乙烯,諸如氟苯乙烯、氯苯乙烯、溴苯乙烯及碘苯乙烯;具有烷氧基取代基之苯乙烯,諸如甲氧基苯乙烯、乙氧基苯乙烯及丙氧基苯乙烯;4-羥基苯乙烯、對羥基-α-甲基苯乙烯、乙醯基苯乙烯;乙烯基甲苯、二乙烯基苯、乙烯基苯酚、鄰
乙烯基苄基甲醚、間乙烯基苄基甲醚、對乙烯基苄基甲醚、鄰乙烯基苄基縮水甘油醚、間乙烯基苄基縮水甘油醚、對乙烯基苄基縮水甘油醚或類似者。
衍生自上文所例示之化合物的結構單元可單獨或以其兩者或更多者之組合形式包含於共聚物中。
在上文中,考慮到聚合特性,較佳為苯乙烯化合物。
考慮到耐化學性,以構成共聚物之結構單元的總莫耳數計,結構單元(A-2)之量可為2至70莫耳%,較佳為5至60莫耳%。
(A-3)衍生自不同於結構單元(A-1)及(A-2)之烯系不飽和化合物的結構單元
除結構單元(A-1)及(A-2)外,本發明之共聚物可進一步包含衍生自不同於結構單元(A-1)及(A-2)之烯系不飽和化合物的結構單元(A-3)。
不同於結構單元(A-1)及(A-2)之烯系不飽和化合物的特定實例可包含不飽和羧酸酯,諸如(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸丁酯、(甲基)丙烯酸二甲基胺基乙酯、(甲基)丙烯酸異丁酯、(甲基)丙烯酸第三丁酯、(甲基)丙烯酸環己酯、(甲基)丙烯酸乙基己酯、(甲基)丙烯酸四氫呋喃酯、(甲基)丙烯酸羥基乙酯、(甲基)丙烯酸2-羥基丙酯、(甲基)丙烯酸2-羥基-3-氯丙酯、(甲基)丙烯酸4-羥基丁酯、(甲基)丙烯酸甘油酯、α-羥基甲基丙烯酸甲酯、α-羥基甲基丙烯酸乙酯、α-羥基甲基丙烯酸丙酯、α-羥基甲基丙烯酸丁酯、(甲基)丙烯酸2-甲氧基乙酯、(甲基)丙烯酸3-甲氧
基丁酯、乙氧基二乙二醇(甲基)丙烯酸酯、甲氧基三乙二醇(甲基)丙烯酸酯、甲氧基三丙二醇(甲基)丙烯酸酯、聚(乙二醇)甲醚(甲基)丙烯酸酯、(甲基)丙烯酸四氟丙酯、(甲基)丙烯酸1,1,1,3,3,3-六氟異丙酯、(甲基)丙烯酸八氟戊酯、(甲基)丙烯酸十七氟癸酯、(甲基)丙烯酸異冰片酯、(甲基)丙烯酸二環戊酯、(甲基)丙烯酸二環戊烯酯、(甲基)丙烯酸二環戊氧基乙酯及(甲基)丙烯酸二環戊烯氧基乙酯;含有N-乙烯基之三級胺,諸如N-乙烯吡咯啶酮、N-乙烯基咔唑及N-乙烯基嗎啉;不飽和醚,諸如乙烯基甲醚及乙烯基乙醚;含有環氧基之烯系不飽和化合物,諸如(甲基)丙烯酸縮水甘油酯、(甲基)丙烯酸3,4-環氧基丁酯、(甲基)丙烯酸4,5-環氧基戊酯、(甲基)丙烯酸5,6-環氧基己酯、(甲基)丙烯酸6,7-環氧基庚酯、(甲基)丙烯酸2,3-環氧基環戊基甲酯、(甲基)丙烯酸3,4-環氧基環己基甲酯、丙烯酸α-乙基縮水甘油酯、丙烯酸α-正丙基縮水甘油酯、丙烯酸α-正丁基縮水甘油酯、N-(4-(2,3-環氧基丙氧基)-3,5-二甲基苯甲基)丙烯醯胺、N-(4-(2,3-環氧基丙氧基)-3,5-二甲基苯基丙基)丙烯醯胺、(甲基)丙烯酸4-羥基丁酯縮水甘油醚、烯丙基縮水甘油醚及2-甲基烯丙基縮水甘油醚;及不飽和醯亞胺,諸如N-苯基順丁烯二醯亞胺、N-(4-氯苯基)順丁烯二醯亞胺、N-(4-羥苯基)順丁烯二醯亞胺及N-環己基順丁烯二醯亞胺。
衍生自上文所例示之化合物的結構單元可單獨或以其兩者或更多者之組合形式包含於共聚物中。
特定而言,結構單元(A-3)可衍生自含有環氧基之烯系不飽和化合物及/或不飽和醯亞胺,較佳地,考慮到
改良共聚特性及絕緣膜之強度,可使用(甲基)丙烯酸縮水甘油酯、(甲基)丙烯酸4-羥基丁酯縮水甘油醚及/或N上經取代之順丁烯二醯亞胺。
以構成共聚物之結構單元的總莫耳數計,結構單元(A-3)之量可為10至80莫耳%,較佳為20至75莫耳%。在此量範圍內,可維持黑色感光性樹脂組合物之儲存穩定性且可改良保持率。
具有結構單元(A-1)至(A-3)之共聚物的實例可包含(甲基)丙烯酸/苯乙烯共聚物、(甲基)丙烯酸/(甲基)丙烯酸苄酯共聚物、(甲基)丙烯酸/苯乙烯/(甲基)丙烯酸甲酯共聚物、(甲基)丙烯酸/苯乙烯(甲基)丙烯酸甲酯/(甲基)丙烯酸縮水甘油酯共聚物、(甲基)丙烯酸/苯乙烯/(甲基)丙烯酸甲酯/(甲基)丙烯酸縮水甘油酯/N-苯基順丁烯二醯亞胺共聚物、(甲基)丙烯酸/苯乙烯/(甲基)丙烯酸甲酯/(甲基)丙烯酸縮水甘油酯/N-環己基順丁烯二醯亞胺共聚物、(甲基)丙烯酸/苯乙烯/(甲基)丙烯酸正丁酯/(甲基)丙烯酸縮水甘油酯/N-苯基順丁烯二醯亞胺共聚物、(甲基)丙烯酸/苯乙烯/(甲基)丙烯酸4-羥基丁酯縮水甘油醚/N-苯基順丁烯二醯亞胺共聚物、(甲基)丙烯酸/苯乙烯/(甲基)丙烯酸縮水甘油酯/N-苯基順丁烯二醯亞胺共聚物或類似者。
一或多種共聚物可包含於黑色感光性樹脂組合物中。
以不包含溶劑之黑色感光性樹脂組合物的總量計(亦即以固體含量計),全部黑色感光性樹脂組合物中之共聚物的量可為5至60wt%,較佳為7至50wt%,更佳為10
至40wt%。在此範圍內,組合物將產生一種塗佈膜,其具有顯影後之良好輪廓及改良的耐化學性。
當藉由凝膠滲透層析法(GPC,使用四氫呋喃作為溶離劑)而測定時,參考聚苯乙烯,由此製備之共聚物的重量平均分子量(Mw)可在3,000至50,000、較佳在5,000至40,000範圍內。在此範圍內,組合物將具有針對基板之良好黏著性、物理/化學特性及黏度。
共聚物可藉由以下而製備:充添分子量調節劑、自由基聚合引發劑、溶劑及提供結構單元(A-1)至(A-3)之各別化合物;引入氮氣;且緩慢攪拌使混合物進行聚合。
分子量調節劑可為硫醇化合物,諸如丁基硫醇及辛基硫醇,或α-甲基苯乙烯二聚體,但不限於此。
自由基聚合引發劑可為諸如2,2'-偶氮二異丁腈、2,2'-偶氮雙(2,4-二甲基戊腈)及2,2'-偶氮雙(4-甲氧基-2,4-二甲基戊腈)之偶氮化合物、過氧化苯甲醯、過氧化月桂基、過氧基特戊酸第三丁酯及1,1-雙(第三丁基過氧基)環己烷,但不限於此。自由基聚合引發劑可單獨或以其兩種或更多種之混合物形式使用。
此外,溶劑可為通常用於製備共聚物之任何溶劑,且可包含例如丙二醇單甲醚乙酸酯(PGMEA)。
(B)環氧樹脂或自其衍生之化合物
本發明之黑色感光性樹脂組合物包含環氧樹脂或自其衍生之化合物。較佳地,環氧樹脂或自其衍生之化合物可具有卡哆主鏈結構(cardo backbone structure)。當參考聚苯乙烯藉由凝膠滲透層析法而測定時,環氧樹脂或自其衍
生之化合物的重量平均分子量可為3,000至18,000,較佳為5,000至10,000。在此範圍內,樹脂組合物將產生一種塗佈膜,其具有良好高度差特性及顯影後之良好圖案輪廓。
在式1中,
X各自獨立地為、、或
;L1各自獨立地為C1-10伸烷基、C3-20環伸烷基或C1-10伸烷氧基;R1至R7各自獨立地為H、C1-10烷基、C1-10烷氧基、C2-10烯基或C6-14;R8為H、甲基、乙基、CH3CHCl-、CH3CHOH-、CH2=CHCH2-或苯基;且n為整數0至10。
C1-10伸烷基之特定實例可包含亞甲基、伸乙基、伸丙基、伸異丙基、伸丁基、伸異丁基、伸第二丁基、伸第三丁基、伸戊基、伸異戊基、伸第三戊基、伸己基、伸庚基、伸辛基、伸異辛基、伸第三辛基、2-乙基伸己基、伸壬基、伸異壬基、伸癸基、伸異癸基或類似者。
C3-20環伸烷基之特定實例可包含伸環丙基、伸環丁基、伸環戊基、伸環己基、伸環庚基、伸十氫萘基、伸金剛烷基或類似者。
C1-10伸烷氧基之特定實例可包含亞甲氧基、伸乙氧基、伸丙氧基、伸丁氧基、伸第二丁氧基、伸第三丁氧基、伸戊氧基、伸己氧基、伸庚氧基、伸辛氧基、2-乙基-伸己氧基或類似者。
C1-10烷基之特定實例可包含甲基、乙基、丙基、異丙基、丁基、異丁基、第二丁基、第三丁基、戊基、異戊基、第三戊基、己基、庚基、辛基、異辛基、第三辛基、2-乙基己基、壬基、異壬基、癸基、異癸基或類似者。
C1-10烷氧基之特定實例可包含甲氧基、乙氧基、丙氧基、丁氧基、第二丁氧基、第三丁氧基、戊氧基、己氧基、庚氧基、辛氧基、2-乙基-己氧基或類似者。
C2-10烯基之特定實例可包含乙烯基、烯丙基、丁烯基、丙烯基或類似者。
C6-14芳基之特定實例可包含苯基、甲苯基、二甲苯基、萘基或類似者。
在反應流程1中,Hal為鹵素;且X、R1、R2及L1與式1中所定義相同。
衍生自具有卡哆主鏈結構之環氧樹脂的化合物可為藉由使具有卡哆主鏈結構之環氧樹脂與不飽和一元酸反應以產生環氧加合物,且隨後使環氧加合物與多元酸酐反應,或藉由使由此獲得之產物與單官能或多官能環氧化合物進一步反應所獲得之化合物。
不飽和一元酸可使用熟知的酸,包含丙烯酸、甲基丙烯酸、丁烯酸、肉桂酸、山梨酸或類似者。
多元酸酐可使用熟知的化合物,包含丁二酸酐、順丁烯二酸酐、偏苯三酸酐、苯均四酸酐、1,2,4,5-環己烷四甲酸二酐、六氫鄰苯二甲酸酐或類似者。
在反應流程2中,
R9各自獨立地為H、C1-10烷基、C1-10烷氧基、C2-10烯基或C6-14芳基;R10及R11各自獨立地為飽和或不飽和C6脂族環或苯環;n為整數1至10;且X、R1、R2及L1與式1中所定義相同。
當使用具有卡哆主鏈結構之環氧樹脂或自其衍生之化合物時,卡哆主鏈結構可改良固化產物與基板之間的黏著性、抗鹼性、可加工性、強度等,且可在藉由顯影移除未固化部分後自細微圖案產生較準確的圖像。
以不包含溶劑之黑色感光性樹脂組合物的總重量計(亦即以固體含量計),環氧樹脂或自其衍生之化合物的量可為5至50wt%,較佳為7至40wt%,更佳為10至35wt%。在所述範圍內,可改良解析度及耐化學性,且可有利地獲得維持圖案形狀之圖案輪廓,所述形狀具有針對圖案之間的所要界限寬度(所允許之寬度)的恆定高度差。
如上文所述,本發明之黑色感光性樹脂組合物以黑色感光性樹脂組合物之總重量計(以固體含量計)可包含10至40wt%丙烯酸共聚物(A),且以黑色感光性樹脂組合物之總重量計(以固體含量計)可包含10至40wt%環氧樹脂或自其衍生之化合物(B)。在此情況下,丙烯酸共聚物(A)與環氧樹脂或自其衍生之化合物(B)的重量比可為40-80:60-20,且特定而言為40-75:60-25。
(C)不同於(A)及(B)之環氧化合物
本發明之黑色感光性樹脂組合物包含除(A)及(B)外之環氧化合物,且所述環氧化合物可為具有衍生自具
有環氧基及不飽和雙鍵的單體之結構單元的均聚物或共聚物。
具有環氧基及不飽和雙鍵之單體的實例可包含(甲基)丙烯酸縮水甘油酯、丙烯酸4-羥基丁酯縮水甘油醚、(甲基)丙烯酸3,4-環氧基丁酯、(甲基)丙烯酸4,5-環氧基戊酯、(甲基)丙烯酸5,6-環氧基己酯、(甲基)丙烯酸6,7-環氧基庚酯、(甲基)丙烯酸2,3-環氧基環戊基甲酯、(甲基)丙烯酸3,4-環氧基環己基甲酯、丙烯酸α-乙基縮水甘油酯、丙烯酸α-正丙基縮水甘油酯、丙烯酸α-正丁基縮水甘油酯、N-(4-(2,3-環氧基丙氧基)-3,5-二甲基苯甲基)丙烯醯胺、N-(4-(2,3-環氧基丙氧基)-3,5-二甲基苯基丙基)丙烯醯胺、烯丙基縮水甘油醚、2-甲基烯丙基縮水甘油醚、鄰乙烯基苄基縮水甘油醚、間乙烯基苄基縮水甘油醚、對乙烯基苄基縮水甘油醚或其混合物,較佳為(甲基)丙烯酸縮水甘油酯、丙烯酸4-羥基丁酯縮水甘油醚或(甲基)丙烯酸3,4-環氧基環己基甲酯。
可與具有環氧基及不飽和雙鍵之單體共聚的其他單體包含選自由以下組成之群的至少一者:不飽和羧酸酯,諸如(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸丁酯、(甲基)丙烯酸二甲基胺基乙酯、(甲基)丙烯酸異丁酯、(甲基)丙烯酸第三丁酯、(甲基)丙烯酸環己酯、(甲基)丙烯酸乙基己酯、(甲基)丙烯酸四氫呋喃酯、(甲基)丙烯酸羥基乙酯、(甲基)丙烯酸2-羥基丙酯、(甲基)丙烯酸2-羥基-3-氯丙酯、(甲基)丙烯酸4-羥基丁酯、(甲基)丙烯酸甘油酯、甲基-α-羥基甲基丙烯酸酯、乙基-α-羥基甲基丙烯酸酯、丙基-α-羥基甲基丙烯酸酯、丁基-α-羥基甲基丙烯酸酯、(甲基)丙烯
酸2-甲氧基乙酯、(甲基)丙烯酸3-甲氧基丁酯、乙氧基二乙二醇(甲基)丙烯酸酯、甲氧基三乙二醇(甲基)丙烯酸酯、甲氧基三丙二醇(甲基)丙烯酸酯、聚(乙二醇)甲醚(甲基)丙烯酸酯、(甲基)丙烯酸四氟丙酯、(甲基)丙烯酸1,1,1,3,3,3-六氟異丙酯、(甲基)丙烯酸八氟戊酯、(甲基)丙烯酸十七氟癸酯、(甲基)丙烯酸異冰片酯、(甲基)丙烯酸二環戊酯、(甲基)丙烯酸二環戊烯酯、(甲基)丙烯酸二環戊氧基乙酯及(甲基)丙烯酸二環戊烯氧基乙酯;不飽和醯亞胺,諸如順丁烯二醯亞胺、N-苯基順丁烯二醯亞胺、N-(4-氯苯基)順丁烯二醯亞胺、N-(4-羥苯基)順丁烯二醯亞胺及N-環己基順丁烯二醯亞胺、(甲基)丙烯酸苯酯、(甲基)丙烯酸苄酯、(甲基)丙烯酸2-苯氧基乙酯、苯氧基二乙二醇(甲基)丙烯酸酯、對壬基苯氧基聚乙二醇(甲基)丙烯酸酯、對壬基苯氧基聚丙二醇(甲基)丙烯酸酯、(甲基)丙烯酸三溴苯酯;苯乙烯;含有烷基取代基之苯乙烯,諸如甲基苯乙烯、二甲基苯乙烯、三甲基苯乙烯、乙基苯乙烯、二乙基苯乙烯、三乙基苯乙烯、丙基苯乙烯、丁基苯乙烯、己基苯乙烯、庚基苯乙烯及辛基苯乙烯;具有鹵素之苯乙烯,諸如氟苯乙烯、氯苯乙烯、溴苯乙烯及碘苯乙烯;具有烷氧基取代基之苯乙烯,諸如甲氧基苯乙烯、乙氧基苯乙烯及丙氧基苯乙烯;4-羥基苯乙烯、對羥基-α-甲基苯乙烯、乙醯基苯乙烯;乙烯基甲苯、二乙烯基苯、乙烯基苯酚、鄰乙烯基苄基甲醚、間乙烯基苄基甲醚及對乙烯基苄基甲醚。
本發明中所使用之環氧化合物可藉由習知方法而合成。
同時,可將烯系不飽和羧酸、烯系不飽和羧酸酐
或其混合物添加至衍生自具有環氧基及不飽和雙鍵之單體的(共)聚合物中,且可發生聚合以產生側鏈中具有環氧基及雙鍵之共聚物。
烯系不飽和羧酸、烯系不飽和羧酸酐或其混合物可為選自由以下組成之群的至少一者:不飽和單羧酸,諸如(甲基)丙烯酸、丁烯酸、α-氯丙烯酸及肉桂酸;不飽和二羧酸及其酸酐,諸如順丁烯二酸、順丁烯二酸酐、反丁烯二酸、衣康酸、衣康酸酐、檸康酸、檸康酸酐及甲基反丁烯二酸;三價或更高之不飽和聚羧酸及其酸酐;及二價或更高之聚羧酸的單[(甲基)丙烯醯氧基烷基]酯,諸如單[2-(甲基)丙烯醯氧基乙基]丁二酸酯及單[2-(甲基)丙烯醯氧基乙基]鄰苯二甲酸酯。
考慮到保持率,側鏈中具有環氧基及雙鍵之共聚物為較佳的。
以不包含溶劑之感光性樹脂組合物的總重量計(以固體含量計),環氧化合物之量可為0.1至10wt%,較佳為0.1至5wt%。在此範圍內,可改良顯影之後的黏著性或浸沒於NMP溶劑中之後的黏著性。
當參考聚苯乙烯藉由凝膠滲透層析法而測定時,環氧化合物(衍生自具有環氧基及不飽和雙鍵之單體的(共)聚合物)之重量平均分子量可在1,000至9,000、較佳在1,000至7,000、更佳在2,000至5,000範圍內。在所述重量平均分子量之情況下,可改良黏著性且可獲得良好耐化學性。
(D)光可聚合化合物
本發明之光可聚合化合物為能夠藉由光引發劑之功能而得以聚合之化合物,且可包含通常用於黑色感光性
樹脂組合物之多官能單體、寡聚物或聚合物。
更明確而言,光可聚合化合物可包含具有至少一個烯系不飽和基團之丙烯酸或甲基丙烯酸的單官能或多官能酯化合物。考慮到耐化學性,具有至少兩個官能基之多官能化合物可為較佳的。
光可聚合化合物可選自由以下組成之群:乙二醇二(甲基)丙烯酸酯、丙二醇二(甲基)丙烯酸酯、二乙二醇二(甲基)丙烯酸酯、三乙二醇二(甲基)丙烯酸酯、1,6-己二醇二(甲基)丙烯酸酯、聚乙二醇二(甲基)丙烯酸酯、聚丙二醇二(甲基)丙烯酸酯、丙三醇三(甲基)丙烯酸酯、三羥甲基丙烷三(甲基)丙烯酸酯、季戊四醇三(甲基)丙烯酸酯、季戊四醇三(甲基)丙烯酸酯及丁二酸之單酯、季戊四醇四(甲基)丙烯酸酯、二季戊四醇五(甲基)丙烯酸酯、二季戊四醇六(甲基)丙烯酸酯、二季戊四醇五(甲基)丙烯酸酯及丁二酸之單酯、己內酯改質之二季戊四醇六(甲基)丙烯酸酯、季戊四醇三丙烯酸酯二異氰酸己二酯(季戊四醇三丙烯酸酯與二異氰酸己二酯之反應產物)、三季戊四醇七(甲基)丙烯酸酯、三季戊四醇八(甲基)丙烯酸酯、雙酚A環氧丙烯酸酯、乙二醇單甲醚丙烯酸酯及其混合物,但不限於此。
以不包含溶劑之黑色感光性樹脂組合物的總重量計(亦即以固體含量計),光可聚合化合物之量可為1至50wt%,較佳為5至40wt%。在此範圍內,樹脂組合物將在顯影期間易於形成圖案而不產生諸如底部浮渣之圖案輪廓的缺陷。
(E)光聚合引發劑
本發明中所使用之光聚合引發劑可為任何已知聚合引發劑。
光聚合引發劑可選自由以下組成之群:苯乙酮化合物、非咪唑化合物、三嗪化合物、鎓化合物、安息香化合物、二苯甲酮化合物、二酮化合物、α-二酮化合物、多核醌化合物、噻化合物、重氮化合物、醯亞胺磺酸酯化合物、肟化合物、咔唑化合物、硼酸鋶化合物及其混合物。
針對高敏感度較佳為揭示於以下中之一或多種肟化合物:朝鮮早期公開專利公開案第2004-0007700號、第2005-0084149號、第2008-0083650號、第2008-0080208號、第2007-0044062號、第2007-0091110號、第2007-0044753號、第2009-0009991號、第2009-0093933號、第2010-0097658號、第2011-0059525號、第2011-0091742號、第2011-0026467號及第2011-0015683號及國際公開案第WO 2010/102502號及第WO 2010/133077號。針對高敏感度及解析度較佳為可商購之光聚合引發劑,諸如OXE-01(BASF有限公司)、OXE-02(BASF有限公司)、OXE-03(BASF有限公司)、N-1919(ADEKA有限公司)、NCI-930(ADEKA有限公司)及NCI-831(ADEKA有限公司)。
以感光性樹脂組合物之總固體含量(不包含溶劑)計,所包含之光聚合引發劑的量可為0.01至15wt%,較佳為0.1至10wt%。在此範圍內,可充分獲得藉由暴露之固化,且可製造具有良好彈性恢復率之管柱狀間隔物。
(F)黑色著色劑
本發明之黑色感光性樹脂組合物包含用於賦予
光屏蔽特性之黑色著色劑。
本發明中所使用之黑色著色劑可為黑色無機著色劑、黑色有機著色劑或其混合物。
黑色無機著色劑及黑色有機著色劑可為任何已知材料,且可包含例如藉由《比色指數(color index)》(The Society of Dyers and Colourists printed印刷)歸類為顏料之任何化合物,且可包含任何已知染料。此外,可視需要包含任何諸如藍色之彩色著色劑以添加至黑色著色劑中。
黑色無機著色劑之特定實例可包含碳黑、鈦黑、基於Cu-Fe-Mn之氧化物及諸如合成鐵黑之金屬氧化物。其中,考慮到圖案特性及耐化學性,碳黑為較佳的。
此外,黑色有機著色劑之特定實例可包含苯胺黑、內醯胺黑、苝黑等。其中,考慮到光密度、介電性等,可較佳使用內醯胺黑(例如BASF之黑色582)。
以著色劑之總重量計(以固體含量計),黑色著色劑可包含90wt%或更高之黑色無機著色劑,且可額外包含0至10wt%黑色有機著色劑。在此範圍內,可有利地獲得能夠防止可見光及紅外光區域中之光洩漏的高光密度。
以不包含溶劑之黑色感光性樹脂組合物的總重量計(亦即以固體含量計),黑色著色劑之量可為10至60wt%、20至50wt%、20至45wt%、25至50wt%或25至45wt%。
在此範圍內,可有利地獲得能夠防止光洩漏之高光密度。
特定而言,當本發明之黑色感光性樹脂組合物固化成厚度為1μm之膜時,可獲得0.5至2.5、較佳0.8至2.0、
更佳1.0至2.3、更佳1.0至2.0之光密度。在此範圍內,可有效防止光洩漏。
同時,為了將黑色分散劑分散於本發明之黑色感光性樹脂組合物中,可使用分散劑。所述分散劑可為著色劑之任何已知分散劑。
分散劑之特定實例可包含陽離子界面活性劑、陰離子界面活性劑、非離子界面活性劑、兩性離子界面活性劑、基於矽酮之界面活性劑、基於氟之界面活性劑或類似者。可商購之分散劑可包含BYK有限公司之Disperbyk-182、-183、-184、-185、-2000、-2150、-2155、-2163、-2164等。材料可單獨或以其兩者或更多者之組合形式使用。分散劑可藉由使用預先處理著色劑表面之方法將其添加至著色劑中來使用,或可藉由在製備黑色感光性樹脂組合物之過程中與著色劑共同添加來使用。
此外,在將黑色著色劑與黏合劑混合後,混合物可用於製備黑色感光性樹脂組合物。所述黏合劑可為上文所描述之共聚物(A)、已知共聚物或其混合物。
因此,可以藉由將著色劑與分散劑、黏合劑、溶劑等混合所獲得之著色劑研磨基底的形式將本發明中所使用之著色劑添加至黑色感光性樹脂組合物中。
(G)溶劑
本發明之黑色感光性樹脂組合物可較佳製備為將上文組分與溶劑混合之液體組合物。溶劑可為任何用於黑色感光性樹脂組合物之已知溶劑,只要溶劑與黑色感光性樹脂組合物之組分具有相容性但不具有反應性即可。
所述溶劑之實例可包含二醇醚,諸如乙二醇單乙醚;乙二醇烷基醚乙酸酯,諸如乙基乙二醇乙酸乙醚;酯,諸如2-羥基丙酸乙酯;二乙二醇,諸如二乙二醇單甲醚;丙二醇烷基醚乙酸酯,諸如丙二醇單甲醚乙酸酯及丙二醇丙醚乙酸酯;及乙酸烷氧基烷酯,諸如乙酸3-甲氧基丁酯。溶劑可單獨或以其兩者或更多者之組合形式使用。
溶劑之量不受特定限制,且考慮到最終黑色感光性樹脂組合物之可塗佈性及穩定性,其可為使組合物中除溶劑外之各組分之總濃度(亦即以固體含量計)可為5至70wt%、較佳10至55wt%之量。
(H)界面活性劑
本發明之黑色感光性樹脂組合物視需要可進一步包含界面活性劑,以增強其可塗佈性及防止產生缺陷。
界面活性劑之類型不受特定限制,但較佳為基於氟之界面活性劑、基於矽之界面活性劑及類似者。
可商購之基於矽的界面活性劑可包含由Dow Corning Toray Silicon製造之DC3PA、DC7PA、SH11PA、SH21PA及SH8400,由GE Toshiba Silicon製造之TSF-4440、TSF-4300、TSF-4445、TSF-4446、TSF-4460及TSF-4452,及由BYK製造之BYK-333、BYK 307、BYK 3560、BYK UV 3535、BYK 361N、BYK 354及BYK 399。此等界面活性劑可單獨或以其兩者或更多者之組合形式使用。可商購之基於氟的界面活性劑可包含由Dai Nippon Ink Kagaku Kogyo(DIC)製造之Megaface F-470、F-471、F-475、F-482、F-489、F-563、RS-55等。尤其可使用BYK之BYK 333及BYK 307,DIC之
F-563及Dai Nippon Ink Kagaku Kogyo之Megaface RS-55。
以不包含溶劑之黑色感光性樹脂組合物的總重量計(亦即以固體含量計),界面活性劑之量可為0.01至10wt%,較佳為0.05至5wt%。在所述量範圍內,黑色感光性樹脂組合物可易於塗佈。
(I)矽烷偶合劑
本發明之黑色感光性樹脂組合物視需要可額外包含矽烷偶合劑,其含有選自由以下組成之群的反應性取代基:羧基、(甲基)丙烯醯基、異氰酸酯基、胺基、巰基、乙烯基、環氧基及其組合,所述矽烷偶合劑作為黏著性輔助劑以改良塗層於基板之黏著性。
矽烷偶合劑之類別不受特定限制且可選自由以下組成之群:三甲氧基矽烷基苯甲酸、γ-甲基丙烯醯氧基丙基三甲氧基矽烷、乙烯基三乙醯氧基矽烷、乙烯基三甲氧基矽烷、γ-異氰酸酯基丙基三乙氧基矽烷、γ-縮水甘油氧基丙基三甲氧基矽烷、γ-縮水甘油氧基丙基三乙氧基矽烷、β-(3,4-環氧環己基)乙基三甲氧基矽烷、苯基胺基三甲氧基矽烷及其混合物。
較佳為含有異氰酸酯基之γ-異氰酸酯基丙基三乙氧基矽烷(例如,由Shin-Etsu製造之KBE-9007)或苯基胺基三甲氧基矽烷,其可維持耐化學性且具有塗佈至基板之良好黏著性。
以不包含溶劑之黑色感光性樹脂組合物的總重量計(亦即以固體含量計),矽烷偶合劑之量可為0.01至10wt%,較佳為0.05至5wt%。在此量範圍內,可進一步改良
黑色感光性樹脂組合物之黏著性。
此外,本發明之黑色感光性樹脂組合物可進一步包含其他諸如抗氧化劑及穩定劑之添加劑,只要組合物之物理特性不受不利影響即可。
即使當本發明之黑色感光性樹脂組合物包含大量黑色著色劑(顏料)時,自其製備之固化膜也顯示出良好黏著性、高度差、表面粗糙度及光屏蔽特性。
包含根據本發明之上述組分的黑色感光性樹脂組合物可藉由習知方法而製備,且其一實施例如下。
首先,將黑色著色劑與溶劑預先混合,且隨後使用珠粒研磨機等使其分散,直至獲得黑色著色劑之所要平均粒徑。在此情況下,可視需要使用界面活性劑,且可混合部分或全部共聚物。向分散液中添加其餘共聚物、環氧樹脂或自其衍生之化合物、環氧化合物、光聚合化合物及光引發劑,且視需要添加諸如界面活性劑及矽烷偶合劑之添加劑,或與額外溶劑混合以達到一定濃度。充分攪拌混合物以產生本發明之黑色感光性樹脂組合物。
本發明提供使用黑色感光性樹脂組合物所形成之黑色管柱狀間隔物(BCS)。黑色管柱狀間隔物圖案之實施例展示於圖1中。
黑色管柱狀間隔物可經由以下步驟製成:形成塗佈膜、暴露、顯影及加熱。
在塗佈膜之形成步驟中,藉由旋塗或狹縫塗佈
法、滾塗法、網板印刷法、塗覆器法等將根據本發明之黑色感光性樹脂組合物以例如1至25μm之厚度塗佈於經預處理之基板上,且隨後在70℃至100℃之溫度下歷時1至10分鐘進行預固化以移除溶劑,從而形成塗佈膜。
為了在由此獲得之塗佈膜中形成圖案,安置具有一定形狀之光罩,且照射200至500nm之激活射束。為了製造具有高度差之黑色管柱狀間隔物,可使用具有透光率不同之圖案的光罩以同時實現主管柱狀間隔物及子管柱狀間隔物。可使用低壓汞燈、高壓汞燈、超高壓汞燈、金屬鹵化物燈、氬氣雷射或類似者作為用於照射之光源,且可視需要使用X光線、電子射束等。針對高壓汞燈,暴露強度隨類別、及組合物中各組分之混合比率、及乾燥膜之厚度而變化,且可為500mJ/cm2或更低(以365nm之波長)。
在暴露步驟後,使用諸如碳酸鈉、氫氧化鈉、氫氧化鉀及氫氧化四甲基銨之鹼性水溶液作為顯影溶液來溶解及移除不必要之部分,從而僅維持所暴露之部分以形成圖案。在將藉由顯影所獲得之圖像圖案冷卻至室溫後,在熱空氣習知烘箱類型乾燥爐中在180℃至250℃之溫度下對圖案進行後烘烤達10至60分鐘以獲得所要最終圖案。
因良好物理特性之緣故,由此製造之黑色管柱狀間隔物可適用作LCD、OLED顯示器或類似者之電子部件。LCD、OLED顯示器或類似者可包含除本發明之間隔物外的熟習此項技術者所熟知之部件。即,可應用本發明之黑色管柱狀間隔物之LCD、OLED顯示器或類似者可包含於本發明中。
在下文中,參考以下實例詳細地解釋本發明。然而,實例意欲進一步說明本發明,且其範疇不限於此。
在以下製備實例中,重量平均分子量係藉由凝膠滲透層析法(GPC)使用聚苯乙烯標準而測定。
向配備有回流冷凝器及攪拌器之500mL圓底燒瓶中添加100g含有51mol% N-苯基順丁烯二醯亞胺、4mol%苯乙烯、10mol%丙烯酸4-羥基丁酯縮水甘油醚及35mol%甲基丙烯酸之單體混合物,300g丙二醇單甲醚乙酸酯(PGMEA)作為溶劑,以及2g 2,2'-偶氮雙(2,4-二甲基戊腈)作為自由基聚合引發劑,隨後將溫度升高至70℃且攪拌5小時以產生具有31%固體含量之共聚物。由此獲得之共聚物的酸值為100mg KOH/g,且藉由凝膠滲透層析法(GPC)使用聚苯乙烯標準所測定之重量平均分子量為20,000。
步驟(1):製備9,9-雙[4-(縮水甘油基氧基)苯基]茀
向3,000mL三頸圓底燒瓶中添加200g甲苯、125.4g 4,4'-(9-亞茀基)二苯酚及78.6g表氯醇,且在攪拌下加熱至40℃以獲得溶液。在容器中混合0.1386g溴化第三丁銨與50% NaOH水溶液(3當量),且在攪拌下將混合物緩慢添加至所得溶液中。
將由此獲得之反應混合物加熱至90℃持續1小時以完全移除4,4'-(9-亞茀基)二苯酚,其藉由HPLC或TLC而確定。將反應混合物冷卻至30℃,且在攪拌下向其中添加400mL二氯甲烷及300mL 1N HCl。隨後,分離有機層,用300mL蒸餾水洗滌2次或3次,經硫酸鎂乾燥,且在減壓下
蒸餾以移除二氯甲烷。所得物使用二氯甲烷與甲醇之混合物再結晶以獲得標題化合物,即環氧樹脂化合物。
步驟(2):製備二丙烯酸(((9H-茀-9,9-二基)雙(4,1-伸苯基))雙(氧基))雙(2-羥基丙-3,1-二基酯)(CAS編號143182-97-2)
向1,000mL三頸燒瓶中添加115g在步驟(1)中所獲得之化合物、50mg氯化四甲銨、50mg 2,6-雙(1,1-二甲基乙基)-4-甲基苯酚及35g丙烯酸。將混合物加熱至90至100℃,同時以25mL/min之流動速率吹氣,且進一步加熱至120℃以獲得溶液。攪拌所得溶液約12小時,直至其酸值降至小於1.0mg KOH/g,且隨後冷卻至室溫。在攪拌下將300mL二氯甲烷及300mL蒸餾水添加至反應混合物中。隨後,分離有機層,用300mL蒸餾水洗滌2次或3次,經硫酸鎂乾燥,且在減壓下蒸餾以移除二氯甲烷,從而得到標題化合物。
步驟(3):製備衍生自具有卡哆主鏈結構之環氧樹脂的化合物
將於PGMEA中之在步驟(2)中所獲得之化合物置放於1,000mL三頸燒瓶中,且進一步向其中添加1,2,4,5-苯四甲酸二酐(0.75當量)、1,2,3,6-四氫鄰苯二甲酸酐(0.5當量)及三苯膦(0.01當量)。在攪拌下將反應混合物加熱至120至130℃持續2小時,且隨後冷卻至80至90℃,隨後攪拌6小時。冷卻至室溫後,獲得重量平均分子量(Mw)為6,000且酸值為107mg KOH/g(以固體含量計)之聚合物溶液(49wt%固體含量)。
向配備有攪拌器、溫度計、氮氣替換設備及回流冷凝器之燒瓶中添加450g PGMEA作為溶劑,且向其中添加150g甲基丙烯酸3,4-環氧基環己基甲酯及3g 2,2'-偶氮二異丁腈。進行反應達30分鐘,且替換氮氣。將可分離之燒瓶浸沒於油浴中且攪拌,同時將反應溫度維持在80℃以進行聚合達5小時。由此獲得之固體的濃度為22wt%,且獲得重量平均分子量為5,500之化合物。
向配備有攪拌器、溫度計、氮氣替換設備及回流冷凝器之燒瓶中添加450g PGMEA作為溶劑,且向其中添加150g甲基丙烯酸縮水甘油酯及3g 2,2'-偶氮二異丁腈。進行反應達30分鐘,且替換氮氣。將可分離之燒瓶浸沒於油浴中且攪拌,同時將反應溫度維持在80℃以進行聚合達5小時。由此獲得之固體的濃度為22wt%,且獲得重量平均分子量為4,000之化合物。
向配備有攪拌器、溫度計、氮氣更換設備及回流冷凝器之燒瓶中添加450g PGMEA作為溶劑,且向其中添加150g丙烯酸4-羥基丁酯縮水甘油醚及3g 2,2'-偶氮二異丁腈。進行反應達30分鐘,且替換氮氣。將可分離之燒瓶浸沒於油浴中且攪拌,同時將反應溫度維持在80℃以進行聚合達5小時。由此獲得之固體的濃度為22wt%,且獲得重量平均分子量為7,000之化合物。
有色分散液(F-1)供應自Tokushiki公司,其係藉由以下方法製備;使用塗料振盪器在25℃下分散8g重量平均分子量為12,000至20,000g/mol且酸值為80至150mg KOH/g之丙烯酸共聚物溶液(Tokushiki公司)、8g酸值為100至140mg KOH/g之丙烯酸聚合物分散液(Tokushiki公司)、80g碳黑作為無機黑及384g PGMEA作為溶劑達6小時。使用0.3mm氧化鋯珠粒進行分散。分散完成後,使用過濾器分離珠粒及經分散之溶液,以製備固體含量為23wt%之有色分散液。
有色分散液(F-2)供應自Tokushiki公司,其係藉由以下方法製備;使用塗料振盪器在25℃下分散8g重量平均分子量為12,000至20,000g/mol且酸值為80至150mg KOH/g之丙烯酸共聚物溶液(Tokushiki公司)、8g酸值為100至140mg KOH/g之丙烯酸聚合物分散液(Tokushiki公司)、80g內醯胺黑(黑色582,BASF)作為有機黑及384g PGMEA作為溶劑達6小時。使用0.3mm氧化鋯珠粒進行分散。分散完成後,使用過濾器分離珠粒及經分散之溶液,以製備固體含量為23wt%之有色分散液。
藉由習知方法將4g(固體含量)作為共聚物之在製備實例1中所製備之共聚物(A)、2.8g(固體含量)在製備實例2中所製備之衍生自環氧樹脂的化合物(B)、4.9g
作為光聚合化合物(D)之DPHA(Nippon Kayaku)、0.2g作為光聚合引發劑(E)之肟光引發劑(OXE-03,BASF)、0.2g三嗪引發劑(T-Y,Pharmasynthese)、0.2g(固體含量)在製備實例3中所製備之環氧化合物(C-1)及6.7g(固體含量)在製備實例6中所製備之有色分散液(F-1)混合於81g作為溶劑(G)之PGMEA中,隨後攪拌5小時以製備黑色感光性樹脂組合物。
黑色感光性樹脂組合物係藉由進行實例1中所描述之相同程序而製備,不同之處在於改變如下文表1中所列之各組分的類別及/或量。
使用旋塗器將在實例及比較實例中所製備之黑色感光性樹脂組合物中的每一者塗佈於玻璃基板上,且在100℃下進行預烘烤達100秒以形成塗佈膜。在由此製造之塗佈膜上分別應用100%全色調(F/T)管柱狀間隔物(CS)圖案光罩及30%半色調(H/T)管柱狀間隔物(CS)圖案光罩,且照射波長為365nm之光,其強度為42mJ/cm2,固化膜與光罩之間的間隙為150μm。在檢驗斷點(BP)時間後,在23℃下使用具有0.04wt%氫氧化鉀之經稀釋的水溶液對塗佈膜進行顯影達15秒,且用純水洗滌1分鐘。在烘箱中在230℃下對由此形成之圖案進行後烘烤達30分鐘以獲得固化膜。
(1)評價可塗佈性
將3g黑色感光性樹脂組合物滴加且旋塗至尺寸為10cm×10cm之玻璃基板上以評價可塗佈性。無伯納德單元(Bernard cell)或干擾條之均勻塗佈膜評價為良好(○)。
(2)量測黑色管柱狀間隔物之厚度
在根據上文固化膜之製造方法(參見圖1)獲得主管柱狀間隔物(主CS)及子管柱狀間隔物(子CS)後,厚度A及厚度B中之每一者使用高度差量測設備(SNU(SIS-2000),SNU Precision)進行量測。當厚度差A-B為0.3至0.5μm時,可預期良好高度差特性。
(3)評價黏著性
依照固化膜之製造方法,獲得使用直徑為20μm之30% H/T圖案光罩再現恆定點圖案之暴露強度,且檢驗能夠得以顯影之圖案。若點圖案之最小圖案尺寸為10μm或更小,且在80℃下將圖案浸沒於100% N-甲基吡咯啶酮(NMP)
溶液中達10分鐘後圖案未發生剝離,則黏著性評價為○。另一方面,若點圖案之尺寸大於10μm,或在80℃下將圖案浸沒於NMP溶液中達10分鐘後圖案發生剝離,則黏著性評價為×。
(4)評價黑色基質之表面特性
在依照固化膜之製造方法形成主CS及子CS後,使用掃描電子顯微鏡(SEM,S-4300,Hitachi)觀測各表面。若發現表面粒子聚集,則表面特性評價為不良(×),且若發現表面粒子平滑,則表面特性評價為良好(○)。
(5)量測光密度
不使用光罩進行固化膜之製造以形成在後烘焙後厚度為3.0μm之固化膜。關於固化膜,使用光密度系統(361T,Xlite)在550nm處量測透射率,且獲得關於厚度為1μm之光密度。
如表2中所示,由實例1至7之黑色感光性樹脂組合物所製成的固化膜(主CS及子CS)具有良好可塗佈性、
高度差、針對基板之黏著性、表面粗糙度及光密度。
特定而言,實例之固化膜顯示出0.3至0.5μm之高度差及良好表面粗糙度、可塗佈性及黏著性。因此,圖案形成特性及顯影性二者皆為良好。
相反地,由比較實例1至3之感光性樹脂組合物所製成的不含共聚物、環氧樹脂或自其衍生之化合物以及環氧化合物中的任一者之固化膜具有不良表面粗糙度。
此外,比較實例1及2具有較差高度差特性,且比較實例3顯示出針對基板之較差黏著性。
因此,根據本發明之黑色感光性樹脂組合物可有效用作諸如LCD及OLED顯示器之各種電子裝置中的黑色管柱狀間隔物。
Claims (8)
- 一種黑色感光性樹脂組合物,其包括:(A)丙烯酸共聚物;(B)環氧樹脂或自其衍生之化合物;(C)不同於(A)及(B)之環氧化合物;(D)光可聚合化合物;(E)光引發劑;及(F)黑色著色劑。
- 如申請專利範圍第1項所述的黑色感光性樹脂組合物,其中以所述黑色感光性樹脂組合物之總重量計(以固體含量計),所包括之所述丙烯酸共聚物(A)的量為10至40wt%,且以所述黑色感光性樹脂組合物之總重量計(以固體含量計),所包括之所述環氧樹脂或所述自其衍生之化合物(B)的量為10至40wt%,其中丙烯酸共聚物(A)與環氧樹脂或自其衍生之化合物(B)的重量比為40-80:60-20。
- 如申請專利範圍第1項所述的黑色感光性樹脂組合物,其中以所述黑色感光性樹脂組合物之總重量計(以固體含量計),所包括之所述黑色著色劑(F)的量為10至60wt%。
- 如申請專利範圍第3項所述的黑色感光性樹脂組合物,其中以所述著色劑之總重量計(以固體含量計),所述黑色著色劑(F)包括90wt%或更高之黑色無機著色劑。
- 如申請專利範圍第3項所述的黑色感光性樹脂組合物,其中以所述著色劑之總重量計(以固體含量計),所述黑色著色劑(F)包括0至10wt%黑色有機著色劑。
- 如申請專利範圍第1項所述的黑色感光性樹脂組合物,其中所述環氧樹脂或所述自其衍生之化合物(B)具有卡哆主鏈結構。
- 如申請專利範圍第1項所述的黑色感光性樹脂組合物,其中當所述黑色感光性樹脂組合物固化為具有1μm厚度之膜時,所述黑色感光性樹脂組合物之光密度為0.5至2.5。
- 如申請專利範圍第1項所述的黑色感光性樹脂組合物,其中所述環氧化合物(C)為均聚物或共聚物,其具有衍生自具有環氧基及不飽和雙鍵之單體的結構單元。
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