CN114127637A - 光敏性树脂组合物 - Google Patents
光敏性树脂组合物 Download PDFInfo
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- CN114127637A CN114127637A CN202080050829.6A CN202080050829A CN114127637A CN 114127637 A CN114127637 A CN 114127637A CN 202080050829 A CN202080050829 A CN 202080050829A CN 114127637 A CN114127637 A CN 114127637A
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- carbon atoms
- acid
- resin composition
- photosensitive resin
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- 239000011342 resin composition Substances 0.000 title claims abstract description 52
- 125000006850 spacer group Chemical group 0.000 claims abstract description 16
- 239000011159 matrix material Substances 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 58
- -1 trimethylolpropane tris (3-mercaptopropionic acid) ester Chemical class 0.000 claims description 44
- 239000000203 mixture Substances 0.000 claims description 27
- 239000003999 initiator Substances 0.000 claims description 23
- 239000000126 substance Substances 0.000 claims description 23
- 239000011230 binding agent Substances 0.000 claims description 22
- 229920005989 resin Polymers 0.000 claims description 22
- 239000011347 resin Substances 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 239000003086 colorant Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
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- PMNLUUOXGOOLSP-UHFFFAOYSA-N 2-mercaptopropanoic acid Chemical compound CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 claims description 8
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- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
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- 229910052736 halogen Inorganic materials 0.000 claims description 8
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
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- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
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- ZOKCNEIWFQCSCM-UHFFFAOYSA-N (2-methyl-4-phenylpent-4-en-2-yl)benzene Chemical compound C=1C=CC=CC=1C(C)(C)CC(=C)C1=CC=CC=C1 ZOKCNEIWFQCSCM-UHFFFAOYSA-N 0.000 claims description 2
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- MJQWABQELVFQJL-UHFFFAOYSA-N 3-Mercapto-2-butanol Chemical compound CC(O)C(C)S MJQWABQELVFQJL-UHFFFAOYSA-N 0.000 claims description 2
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- OBDVFOBWBHMJDG-UHFFFAOYSA-N 3-mercapto-1-propanesulfonic acid Chemical compound OS(=O)(=O)CCCS OBDVFOBWBHMJDG-UHFFFAOYSA-N 0.000 claims description 2
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- BVFUUJNISLPELF-UHFFFAOYSA-N 4-oxo-4-(2-sulfanylethylamino)butanoic acid Chemical compound OC(=O)CCC(=O)NCCS BVFUUJNISLPELF-UHFFFAOYSA-N 0.000 claims description 2
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- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 2
- ZNEWHQLOPFWXOF-UHFFFAOYSA-N coenzyme M Chemical compound OS(=O)(=O)CCS ZNEWHQLOPFWXOF-UHFFFAOYSA-N 0.000 claims description 2
- 238000004132 cross linking Methods 0.000 claims description 2
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- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 claims description 2
- 229960003151 mercaptamine Drugs 0.000 claims description 2
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 claims description 2
- KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 claims description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 2
- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 claims description 2
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Abstract
本发明涉及一种光敏性树脂组合物,更详细地,涉及一种实现微细图案的同时具有高的残膜率,从而适合形成柱状隔垫物、黑色矩阵或着色(例如,黑色)的柱状隔垫物,因此可以用于包括OLED显示器和TFT‑LCD面板在内的各种电子元件的光敏性树脂组合物。
Description
技术领域
本发明涉及一种光敏性树脂组合物,更详细地,涉及一种实现微细图案的同时具有高的残膜率,从而适合形成柱状隔垫物、黑色矩阵或着色(例如,黑色)的柱状隔垫物,因此可以用于包括OLED显示器和TFT-LCD面板在内的各种电子元件光敏性树脂组合物。
背景技术
近年来,显示器产业大致分为TV用显示器、笔记本电脑和计算机显示器用的中小型显示器和10英寸以下的移动显示器市场。由于显示器市场每年都需要高清晰度的产品,具有应提高TFT-LCD的集成度的问题,并且由于LCD的价格降低,还需要降低生产成本。
液晶显示元件中的黑色矩阵、柱状隔垫物等起到保持上板和下板的间隙的作用,并且为了形成这种微细图案,光敏性组合物应具有提高的残膜率、灵敏度、显影对比度、清晰度、高分子树脂的溶解性、与基板的粘合力和电路线宽均匀度(CD均匀性(CDuniformity))。
柱状隔垫物图案的示例性的结构如图1所示。这种柱状隔垫物图案中,若在相同的底部临界尺寸(Bottom CD(critical dimension)size)下可以提高残膜率,则制备工艺时减少抗蚀材料的消耗,从而可以降低产品价格。
现有的光敏性树脂组合物通过使用特定结构的光聚合引发剂来实现微细图案或通过诸如自由基捕获剂的其它添加物来实现微细图案(例:韩国授权专利第10-1435652号)。但是,从现有的光聚合引发剂通过曝光而产生的自由基官能团为了制作微细图案,而使用了减少引发剂含量的方法,但其具有降低残膜率的缺点。
发明内容
要解决的技术问题
本发明的目的在于解决上述现有技术的问题,要解决的技术问题在于提供一种可以实现微细图案的同时可以提高残膜率的光敏性树脂组合物。
技术方案
为了解决上述技术问题,本发明提供一种光敏性树脂组合物,其包含:(a)碱溶性粘合剂树脂;(b)任意的光聚合性化合物;(c)具有由以下化学式1表示的结构的光聚合引发剂;和(d)有机溶剂,基于所述(a)碱溶性粘合剂树脂和(b)任意的光聚合性化合物的总和100重量份,所述光敏性树脂组合物包含0.7-20重量份的所述(c)光聚合引发剂。
[化学式1]
所述化学式1中,R1、R2和R4-R10各自独立地表示氢、卤素、碳原子数为1-20个的直链或支链烷基、碳原子数为6-20个的芳基、碳原子数为1-20个的烷氧基、碳原子数为7-40个的芳烷基、碳原子数为1-20个的羟烷基、碳原子数为2-40个的羟基烷氧基烷基或者碳原子数为3-20个的环烷基,R3表示碳原子数为6-20个的芳基。
一个具体实施方案中,本发明的光敏性树脂组合物可以进一步包含用于调节分子量的链转移剂。
根据本发明的另一个方面,提供一种由本发明的光敏性树脂组合物形成的微细图案化固化物。
有益效果
本发明的光敏性树脂组合物可以实现微细图案的同时,可以提高残膜率,从而适合形成柱状隔垫物、黑色矩阵或着色(例如,黑色)的柱状隔垫物,因此可以用于包括OLED显示器和TFT-LCD面板在内的各种电子元件。
附图说明
图1是柱状隔垫物图案的示例性结构。
图2是示出根据本发明的实施例和比较例中使用的光聚合引发剂的种类的残膜率的图表。
图3是示出将本发明的实施例中使用的光引发剂C和比较例7中使用的光引发剂OXE-01的根据吸收光波长的吸光度进行比较的图表。
具体实施方式
以下,对本发明进行更详细的说明。
本发明的光敏性树脂组合物包含(a)碱溶性粘合剂树脂。
一个具体实施方案中,作为所述碱溶性粘合剂树脂,可以使用丙烯酸聚合物或在侧链具有丙烯酸不饱和键的丙烯酸聚合物。
所述丙烯酸聚合物是指丙烯酸基单体的聚合物(包含均聚物或共聚物),这种单体的实例可以列举(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸丙酯、(甲基)丙烯酸丁酯、(甲基)丙烯酸戊酯、(甲基)丙烯酸己酯、(甲基)丙烯酸环己酯、(甲基)丙烯酸庚酯、(甲基)丙烯酸辛酯、(甲基)丙烯酸壬酯、(甲基)丙烯酸癸酯、(甲基)丙烯酸月桂酯、(甲基)丙烯酸十二烷基酯、(甲基)丙烯酸十四烷基酯、(甲基)丙烯酸十六烷基酯、(甲基)丙烯酸异冰片酯、(甲基)丙烯酸金刚烷基酯、(甲基)丙烯酸二环戊基酯、(甲基)丙烯酸二环戊烯基酯、(甲基)丙烯酸苄酯、2-甲氧基乙基(甲基)丙烯酸酯、2-乙氧基乙基(甲基)丙烯酸酯、(甲基)丙烯酸衣康酸、马来酸、马来酸酐、马来酸单烷基酯、衣康酸单烷基酯、富马酸单烷基酯、(甲基)丙烯酸缩水甘油酯、3,4-环氧丁基(甲基)丙烯酸酯、2,3-环氧环己基(甲基)丙烯酸酯、3,4-环氧环己基甲基(甲基)丙烯酸酯、3-甲基氧杂环丁烷-3-甲基(甲基)丙烯酸酯、3-乙基氧杂环丁烷-3-甲基(甲基)丙烯酸酯、苯乙烯、α-甲基苯乙烯、乙酰氧基苯乙烯、N-甲基马来酰亚胺、N-乙基马来酰亚胺、N-丙基马来酰亚胺、N-丁基马来酰亚胺、N-环己基马来酰亚胺、(甲基)丙烯酰胺或N-甲基(甲基)丙烯酰胺等,并且它们可以各自单独使用或者两种以上一同使用。
此外,作为所述在侧链具有丙烯酸不饱和键的丙烯酸聚合物,可以使用含有羧酸的丙烯酸聚合物与环氧树脂进行加成反应的共聚物。根据一个具体实施方案,可以使用例如在40-180℃的温度下将含有羧酸的丙烯酸共聚物与(甲基)丙烯酸缩水甘油酯、3,4-环氧丁基(甲基)丙烯酸酯、2,3-环氧环己基(甲基)丙烯酸酯或3,4-环氧环己基甲基(甲基)丙烯酸酯等环氧化合物进行加成反应而获得的粘合剂树脂,其中,所述含有羧酸的丙烯酸共聚物是通过将(甲基)丙烯酸、衣康酸、马来酸或马来酸单烷基酯等含有羧酸的丙烯酸单体与两种以上的(甲基)丙烯酸甲酯、(甲基)丙烯酸己酯等的(甲基)丙烯酸烷基酯、(甲基)丙烯酸环己酯、(甲基)丙烯酸异冰片酯、(甲基)丙烯酸金刚烷基酯、(甲基)丙烯酸二环戊基酯、(甲基)丙烯酸二环戊烯基酯、(甲基)丙烯酸苄酯、2-甲氧基乙基(甲基)丙烯酸酯、2-乙氧基乙基(甲基)丙烯酸酯、苯乙烯、α-甲基苯乙烯、乙酰氧基苯乙烯、N-甲基马来酰亚胺、N-乙基马来酰亚胺、N-丙基马来酰亚胺、N-丁基马来酰亚胺、N-环己基马来酰亚胺、(甲基)丙烯酰胺或N-甲基(甲基)丙烯酰胺等单体进行共聚而获得。
作为在侧链具有丙烯酸不饱和键的丙烯酸聚合物的另一个实例,可以列举将含有环氧基的丙烯酸共聚物与含有羧酸的化合物进行加成反应的共聚物。根据一个具体实施方案,可以使用例如在40-180℃的温度下将含有环氧基的丙烯酸共聚物与(甲基)丙烯酸、衣康酸、马来酸或马来酸单烷基酯等含有羧酸的丙烯酸单体进行加成反应而获得的粘合剂树脂,其中,所述含有环氧基的丙烯酸共聚物是将(甲基)丙烯酸缩水甘油酯、3,4-环氧丁基(甲基)丙烯酸酯、2,3-环氧环己基(甲基)丙烯酸酯或3,4-环氧环己基甲基(甲基)丙烯酸酯等含有环氧基的丙烯酸单体与两种以上的(甲基)丙烯酸缩水甘油酯或(甲基)丙烯酸己酯等(甲基)丙烯酸烷基酯、(甲基)丙烯酸环己酯、(甲基)丙烯酸异冰片酯、(甲基)丙烯酸金刚烷基酯、(甲基)丙烯酸二环戊基酯、(甲基)丙烯酸二环戊烯基酯、(甲基)丙烯酸苄酯、2-甲氧基乙基(甲基)丙烯酸酯、2-乙氧基乙基(甲基)丙烯酸酯、苯乙烯、α-甲基苯乙烯、乙酰氧基苯乙烯、N-甲基马来酰亚胺、N-乙基马来酰亚胺、N-丙基马来酰亚胺、N-丁基马来酰亚胺、N-环己基马来酰亚胺、(甲基)丙烯酰胺或N-甲基(甲基)丙烯酰胺等单体进行共聚而获得。
根据本发明的一个具体实施方案,所述碱溶性粘合剂树脂的重均分子量可以为1000以上、2000以上、3000以上或4000以上,而且可以为300000以下、200000以下、100000以下、50000以下或40000以下,但并不限定于此。
根据本发明的一个具体实施方案,所述碱溶性粘合剂树脂的分散度可以为1.0以上、1.2以上或1.5以上,而且可以为10.0以下、5.0以下或3.0以下,但并不限定于此。
根据本发明的一个具体实施方案,除了所述碱溶性粘合剂树脂之外,还可以进一步使用含有丙烯酸酯基的粘合剂树脂或线型酚醛(Novolak)或双酚类型的碱溶性聚合物。在销售的产品中可以进一步使用的粘合剂树脂有日本化药(Nippon Kayaku)公司的PCR-122H、PCR-1173H、PCR-1221H、PCR-1220H、CCR-1171H、CCR-1307H、CCR-1309H、ZAR-1494H、ZAR-2001H、ZFR-1491H、ZFR-1554H等,但并不限定于此。
所述碱溶性粘合剂树脂可以是不受各聚合单元的排列顺序限制的无规共聚物,但并不限定于此。
本发明的光敏性树脂组合物中,可以根据需要适当调节所述碱溶性粘合剂树脂的含量,例如,相对于组合物总100重量份,可以为3重量份以上、5重量份以上、7重量份以上、9重量份以上或10重量份以上,而且可以为99重量份以下、90重量份以下、80重量份以下、70重量份以下、60重量份以下、50重量份以下、45重量份以下、40重量份以下、35重量份以下或30重量份以下,但并不限定于此。
本发明的光敏性树脂组合物可以包含(b)作为任意成分的光聚合性化合物。
所述光聚合性化合物可以为具有至少2个以上的乙烯基双键的交联型单体。
一个具体实施方案中,作为所述光聚合性化合物,例如,可以使用通过使环氧乙烷基的数量为2-20的聚乙二醇二(甲基)丙烯酸酯、乙二醇二(甲基)丙烯酸酯、环氧丙烷基的数量为2-14的聚丙二醇二(甲基)丙烯酸酯、丙二醇二(甲基)丙烯酸酯、三羟甲基丙烷二(甲基)丙烯酸酯、双酚A和二缩水甘油醚丙烯酸的加成反应产物、乙基异氰尿酸三(甲基)丙烯酸酯、β-羟乙基(甲基)丙烯酸酯的邻苯二甲酸二酯、β-羟乙基(甲基)丙烯酸酯和甲苯二异氰酸酯的加成反应产物、三羟甲基丙烷三(甲基)丙烯酸酯、四羟甲基甲烷四(甲基)丙烯酸酯、季戊四醇三(甲基)丙烯酸酯、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、二季戊四醇三(甲基)丙烯酸酯、三羟甲基和丙烷三缩水甘油醚丙烯酸的加成反应产物、线型酚醛环氧树脂和(甲基)丙烯酸的加成反应产物与邻苯二甲酸酐反应而形成的线型酚醛环氧丙烯酸酯树脂或它们的组合,但并不限定于此。
另一个具体实施方案中,作为所述光聚合性化合物,可以使用异氰脲酸酯化合物。可以用作光聚合性化合物的异氰脲酸酯化合物,可以列举单烯丙基二缩水甘油基异氰脲酸酯化合物、二烯丙基单缩水甘油基异氰脲酸酯化合物、三烯丙基异氰脲酸酯化合物等。
具体地,作为所述单烯丙基二缩水甘油基异氰脲酸酯化合物的实例,可以列举单烯丙基二缩水甘油基异氰脲酸酯、1-烯丙基-3,5-双(2-甲基环氧丙基)异氰脲酸酯、1-(2-甲基丙烯基)-3,5-二缩水甘油基异氰脲酸酯、1-(2-甲基丙烯基)-3,5-双(2-甲基环氧丙基)异氰脲酸酯等,作为所述二烯丙基单缩水甘油基异氰脲酸酯化合物的实例,可以列举二烯丙基单缩水甘油基异氰脲酸酯、1,3-二烯丙基-5-(2-甲基环氧丙基)异氰脲酸酯、1,3-双(2-甲基丙烯基)-5-缩水甘油基异氰脲酸酯、1,3-双(2-甲基丙烯基)-5-(2-甲基环氧丙基)异氰脲酸酯等,作为所述三烯丙基异氰脲酸酯化合物的实例,可以列举三烯丙基异氰脲酸酯、三(2-甲基丙烯基)异氰脲酸酯等,并且可以将选自它们中的任一种或两种以上混合使用,但并不限定于此。
本发明的光敏性树脂组合物中,包含所述光聚合性化合物时,根据需要可以适当调节其含量,例如,相对于组合物总100重量份,可以为2重量份以上、4重量份以上、6重量份以上、8重量份以上或10重量份以上,而且可以为70重量份以下、65重量份以下、60重量份以下、55重量份以下或50重量份以下,但并不限定于此。
本发明的光敏性树脂组合物包含(c)具有由以下化学式1表示的结构的光聚合引发剂。
[化学式1]
所述化学式1中,R1、R2和R4-R10各自独立地表示氢、卤素、碳原子数为1-20个的直链或支链烷基、碳原子数为6-20个的芳基、碳原子数为1-20个的烷氧基、碳原子数为7-40个的芳烷基、碳原子数为1-20个的羟烷基、碳原子数为2-40个的羟基烷氧基烷基或碳原子数为3-20个的环烷基;R3表示碳原子数为6-20个的芳基。
更具体地,所述化学式1中,R1、R2和R4-R10各自独立地表示氢、卤素、碳原子数为1-16个的直链或支链烷基、碳原子数为6-14个的芳基、碳原子数为1-16个的烷氧基、碳原子数为7-30个的芳烷基、碳原子数为1-16个的羟烷基、碳原子数为2-32个的羟基烷氧基烷基或碳原子数为3-16个的环烷基,R3表示碳原子数为6-14个的芳基。
进一步具体地,所述化学式1中,R1、R2和R4-R10各自独立地表示氢、卤素、碳原子数为1-10个的直链或支链烷基、碳原子数为6-10个的芳基、碳原子数为1-10个的烷氧基、碳原子数为7-20个的芳烷基、碳原子数为1-10个的羟烷基、碳原子数为2-20个的羟基烷氧基烷基或碳原子数为3-10个的环烷基,R3表示碳原子数为6-10个的芳基。
进一步具体地,所述化学式1中,R1、R2和R4-R10各自独立地表示氢、卤素、碳原子数为1-6个的直链或支链烷基、碳原子数为6-10个的芳基、碳原子数为1-6个的烷氧基、碳原子数为7-16个的芳烷基、碳原子数为1-6个的羟烷基、碳原子数为2-12个的羟基烷氧基烷基或碳原子数为3-6个的环烷基,R3表示碳原子数为6-10个的芳基。
所述化学式1中,所述直链或支链烷基、芳基、烷氧基、芳烷基、羟烷基、羟基烷氧基烷基、环烷基可以各自独立地为未取代的,或者可以被卤素、碳原子数为1-6个的直链或支链烷基或碳原子数为3-6个的环烷基取代。
根据本发明的一个具体实施方案,所述化学式1中,R1可以各自独立地为氢、甲基、乙基、丙基或丁基;R2可以为甲基、乙基、丙基或丁基;R3可以为苯基;R4-R10可以为氢。
具有由所述化学式1表示的结构的光聚合引发剂向本发明的光敏性树脂组合物赋予优异的残膜率特性,特别地,与在R3位置具有烷基(例如,甲基、乙基等)的现有的光聚合引发剂相比,在相同的微细图案尺寸下赋予显著优异的残膜率特性。
在本发明的光敏性树脂组合物中,基于所述(a)碱溶性粘合剂树脂和(b)任意成分的光聚合性化合物的总和100重量份,包含0.7-20重量份的所述(c)化学式1的光聚合引发剂。基于(a)碱溶性粘合剂树脂和(b)任意成分的光聚合性化合物的总和100重量份,当本发明的光敏性树脂组合物中包含的所述(c)化学式1的光聚合引发剂的含量小于0.7重量份时,由于低敏感度,可能会使残膜率变差,并且在图案的形成上存在困难,当所述(c)化学式1的光聚合引发剂的含量超过20重量份时,储存稳定性可能会发生问题,并且由于光聚合引发剂的溶解度减少,可能会在薄膜表面产生异物。
一个具体实施方案中,基于(a)碱溶性粘合剂树脂和(b)光聚合性化合物的总和100重量份,本发明的光敏性树脂组合物中包含的化学式1的光聚合引发剂的含量可以为0.8重量份以上、0.9重量份以上、1.0重量份以上、1.1重量份以上、1.2重量份以上、1.4重量份以上、1.6重量份以上或1.8重量份以上,而且可以为19.5重量份以下、19重量份以下、18.5重量份以下、18重量份以下、16重量份以下、14重量份以下、12重量份以下、10重量份以下或8重量份以下。
本发明的光敏性树脂组合物除了所述化学式1的光聚合引发剂之外,根据需要还可以包含附加的光聚合引发剂。作为本发明中可以进一步使用的光聚合引发剂,可以列举通常使用的三嗪类、苯偶姻类,苯乙酮类,咪唑类,氧杂蒽酮类或肟酯类等光引发剂化合物,更具体地可以列举三苯基氧膦、苯基联苯酮、1-羟基-1-苯甲酰环己烷、苄基二甲基缩酮、1-苄基-1-二甲基氨基-1-(4-吗啉代-苯甲酰)丙烷、2-吗啉基-2-(4-甲基巯基)苯甲酰丙烷、噻吨酮(thioxanthone)、1-氯-4-丙基噻吨酮、异丙基噻吨酮、二乙基噻吨酮、乙基蒽醌、4-苯甲酰基-4-甲基二苯硫醚、苯偶姻丁醚、2-羟基-2-苯甲酰丙烷、2-羟基-2-(4-异丙基)苯甲酰丙烷、4-丁基苯甲酰三氯甲烷(4-butylbenzoyltrichloromethane)、4-苯氧基苯甲酰二氯甲烷、苯甲酰甲酸甲酯、1,7-二(9-吖啶基)庚烷、9-正丁基-3,6-双(2-吗啉代-异丁酰基)咔唑、2-甲基-4,6-双(三氯甲基)-s-三嗪、2-苯基-4,6-双(三氯甲基)-s-三嗪、2-萘基-4,6-双(三氯甲基)-s-三嗪、2-苄基-2-二甲基氨基-1-(4-吗啉代苯基)-1-丁酮、2-甲基-1-[(4-甲硫基)苯基]-2-吗啉代丙烷-1-酮、2,2’-双(2,4-二氯苯基)-4,4’,5,5′-四苯基-1,2’-联咪唑、4,4’-双(二乙基氨基)苯甲酮、2-巯基苯并噻唑、汽巴精化(Ciba SpecialtyChemicals)公司的Irgacure 369、Irgacure 379Irgacur 651、Irgacure 907、DarocurTPO、Irgacure 819、OXE-01、OXE-02、艾迪科(ADEKA)公司的N-1919、NCI-831、三养社的SPI-02、SPI-03、SPI-04、SPI-05等,但并不限定于此。本发明的光敏性树脂组合物包含这种附加的光聚合引发剂时,在可以实现本发明的目的的范围内,根据需要可以适当调节其含量。
本发明的光敏性树脂组合物包含(d)有机溶剂。
作为所述有机溶剂,例如,可以列举:甲醇、乙醇等醇类;二氯***、正丁醚、二异戊醚、苯甲醚、四氢呋喃等醚类;乙二醇单甲醚、乙二醇单***等乙二醇醚类;甲基溶纤剂乙酸酯、乙基溶纤剂乙酸酯、二乙基溶纤剂乙酸酯等溶纤剂乙酸酯类;甲基乙基卡必醇、二乙基卡必醇、二乙二醇单甲醚、二乙二醇单***、二乙二醇二甲醚、二乙二醇甲***、二乙二醇二***等卡必醇类;丙二醇甲醚乙酸酯、丙二醇丙醚乙酸酯等丙二醇烷基醚乙酸酯类;甲苯、二甲苯等芳香族烃类;甲基乙基酮、环己酮、4-羟基-4-甲基-2-戊酮、甲基-正丙基酮、甲基-正丁基酮、甲基-正戊基酮、2-庚酮等酮类;乙酸乙酯、乙酸正丁酯、乙酸异丁酯等饱和脂肪族单羧酸烷基酯类;乳酸甲酯、乳酸乙酯等乳酸酯类;氧基乙酸甲酯、氧基乙酸乙酯、氧基乙酸丁酯等氧基乙酸烷基酯类;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、乙氧基乙酸乙酯等烷氧基乙酸烷基酯类;3-氧代丙酸甲酯、3-氧代丙酸乙酯等3-氧代丙酸烷基酯类;3-甲氧基丙酸甲酯、3-甲氧基丙酸乙酯、3-乙氧基丙酸乙酯、3-乙氧基丙酸甲酯等3-烷氧基丙酸烷基酯类;2-氧代丙酸甲酯、2-氧代丙酸乙酯、2-氧代丙酸丙酯等2-氧代丙酸烷基酯类;2-甲氧基丙酸甲酯、2-甲氧基丙酸乙酯、2-乙氧基丙酸乙酯、2-乙氧基丙酸甲酯等2-烷氧基丙酸烷基酯类;2-氧基-2-甲基丙酸甲酯、2-氧基-2-甲基丙酸乙酯等2-氧基-2-甲基丙酸酯类、2-甲氧基-2-甲基丙酸甲酯、2-乙氧基-2-甲基丙酸乙酯等2-烷氧基-2-甲基丙酸烷基酯类的单氧基单羧酸烷基酯类;2-羟基丙酸乙酯、2-羟基-2-甲基丙酸乙酯、羟基乙酸乙酯、2-羟基-3-甲基丁酸甲酯等酯类;丙酮酸乙酯等酮酸酯类等,并且可以列举N-甲基甲酰胺、N,N-二甲基甲酰胺、N-甲基甲酰苯胺、N-甲基乙酰胺、N,N-二甲基乙酰胺、N-甲基吡咯烷酮、二甲基亚砜、苄基乙基醚、二己基醚、乙酰丙酮、异佛尔酮、己酸、辛酸、1-辛醇、1-壬醇、苄醇、乙酸苄酯、苯甲酸乙酯、草酸二乙酯、马来酸二乙酯、γ-丁内酯、碳酸亚乙酯、碳酸亚丙酯、苯基溶纤剂乙酸酯等。选自上述中的有机溶剂可以单独使用或者两种以上混合使用。
本发明的光敏性树脂组合物中,根据需要,可以适当调节所述有机溶剂的含量,例如,相对于组合物总100重量份,可以为30重量份以上、35重量份以上、40重量份以上、45重量份以上或50重量份以上,而且可以为90重量份以下、85重量份以下、80重量份以下、75重量份以下或70重量份以下,但并不限定于此。本发明的光敏性树脂组合物的固形物浓度没有特别限制,在一个具体实施方案中,固形物浓度可以为10-50重量%,但并不限定于此。
一个具体实施方案中,本发明的光敏性树脂组合物可以进一步包含用于调节分子量的链转移剂。
一个具体实施方案中,作为用于调节分子量的链转移剂,可以使用含有硫原子化合物。所述含有硫原子的链转移剂可以选自例如巯基乙酸、硫代苹果酸、硫代水杨酸、2-巯基丙酸、3-巯基丙酸、3-巯基丁酸、N-(2-巯基丙酰基)甘氨酸、2-巯基烟酸、3-[N-(2-巯基乙基)氨基甲酰基]丙酸、3-[N-(2-巯基乙基)氨基]丙酸、N-(3-巯基丙酰基)丙氨酸、2-巯基乙磺酸、3-巯基丙磺酸、4-巯基丁磺酸、十二烷基(4-甲硫基)苯基醚、2-巯基乙醇、3-巯基-1,2-丙二醇、1-巯基-2-丙醇、3-巯基-2-丁醇、巯基苯酚、2-巯基乙胺、2-巯基咪唑、2-巯基苯并咪唑、2-巯基-3-吡啶酚、2-巯基苯并噻唑、巯基乙酸、三羟甲基丙烷三(3-巯基丙酸)酯、季戊四醇四(3-巯基丙酸乙酸、十二烷基硫醇、2,4-二苯基-4-甲基-1-戊烯、辛硫醇、2-巯基乙醇等硫醇类或它们的组合,但并不限定于此。
本发明的光敏性树脂组合物中包含所述链转移剂时,根据需要,可以适当调节其含量,例如,相对于组合物总100重量份,可以以0.1-10重量份的量包含,更具体为0.2-5重量份的量包含,进一步具体为0.5-2重量份的量包含,但并不限定于此。
此外,一个具体实施方案中,根据需要,本发明的光敏性树脂组合物可以选择性地进一步含有填充剂、其它高分子化合物、热自由基引发剂、紫外线吸收剂、增粘剂、聚合调节剂、pH调节剂、防垢剂、电解质等本技术领域中公知的添加剂。对这些附加添加剂的种类和含量不作特别限制,可以使用本领域中公知的通常的种类和含量。
本发明的光敏性组合物除了上述成分之外,根据需要还可以包含一种以上的附加成分,例如,着色剂、辅助固化剂、助粘剂和/或表面活性剂。
所述着色剂可以包含有机颜料、染料或它们的组合。所述有机颜料可以是选自红色颜料、绿色颜料、蓝色颜料和黄色颜料中的一种或两种以上的混合物。此外,黑色着色剂可以包含黑色无机着色剂、黑色有机着色剂或它们的混合物。
所述红色颜料可以使用色指数(Color Index)中的C.I.红色颜料179、C.I.红色颜料254、C.I.红色颜料255、C.I.红色颜料264、C.I.红色颜料270、C.I.红色颜料272、C.I.红色颜料177、C.I.红色颜料89等,它们可以单独使用或者两种以上混合使用,但并不必须限定于此。
所述绿色颜料可以使用色指数中的诸如C.I.绿色颜料59、C.I.绿色颜料58、C.I.绿色颜料36、C.I.绿色颜料7等卤素取代的酞菁铜颜料等,它们可以单独使用或者两种以上混合使用,但并不必须限定于此。
所述蓝色颜料可以使用色指数中的C.I.蓝色颜料15:6、C.I.蓝色颜料15:0、C.I.蓝色颜料15:1、C.I.蓝色颜料15:2、C.I.蓝色颜料15:3、C.I.蓝色颜料15:4、C.I.蓝色颜料15:5、C.I蓝色颜料15:6、C.I.蓝色颜料16等,它们可以单独使用或者两种以上混合使用,但并不必须限定于此。
所述黄色颜料可以使用色指数中的诸如C.I.黄色颜料139等异吲哚啉基颜料、诸如C.I.黄色颜料138等喹啉黄基颜料、诸如C.I.黄色颜料150等镍配合物颜料、C.I.黄色颜料100等,它们可以单独使用或者两种以上混合使用,但并不必须限定于此。
作为所述黑色无机着色剂的具体的实例,可以使用诸如炭黑、钛黑、Cu-Fe-Mn-基氧化物和合成铁黑的金属氧化物等,它们可以单独使用或者两种以上混合使用,但并不必须限定于此。
作为所述黑色有机着色剂的具体的实例,可以列举苯胺黑、内酰胺黑、苝黑等,可以使用其中的内酰胺黑(例:巴斯夫公司的黑色(Black)582等),它们可以单独使用或者两种以上混合使用,但并不必须限定于此。
使用颜料作为所述着色剂时,为了分散颜料,可以以与分散剂、共聚物树脂、溶剂等混合的着色分散液(色浆(mill base))的形式添加到着色光敏性树脂组合物中。
本发明的光敏性树脂组合物中包含所述着色剂时,根据需要,可以适当调节其含量,例如,相对于组合物总100重量份,可以以1-40重量份的量包含,更具体为2-20重量份的量包含,进一步具体为5-10重量份的量包含,但并不限定于此。
所述辅助固化剂起到提高光引发剂的自由基的形成和薄膜的固化度的作用,作为其实例,可以列举季戊四醇四(3-巯基丙酸酯)、邻苯二甲酸二辛酯、邻苯二甲酸二异壬酯、己二酸二辛酯、磷酸三甲苯酯和2,2,4-三甲基-1,3-戊二醇单异丁酸酯、2-巯基苯并咪唑、2-巯基苯并噻唑、2-巯基苯并恶唑、2,5,-二巯基-1,3,4-噻二唑、2-巯基-4,6-二甲氨基吡啶等,它们可以单独使用或者两种以上混合使用,但并不必须限定于此。本发明的光敏性树脂组合物中包含所述辅助固化剂时,根据需要,可以适当调节其含量,例如,相对于组合物总100重量份,可以以0.1-10重量份的量包含,更具体为0.2-8重量份的量包含,进一步具体为0.4-5重量份的量包含,但并不限定于此。
所述助粘剂起到提高与基板的粘合性的作用,并且为了改善与基板的粘附性等,可以具有乙烯基、羧基、甲基丙烯酰氧基、异氰酸酯基、环氧基等反应性取代基。作为所述助粘剂的实例,可以列举三甲氧基甲硅烷基苯甲酸(Trimethoxysilyl benzoic acid)、γ-甲基丙烯酰氧基丙基三甲氧基硅烷、乙烯基三乙酰氧硅烷、乙烯基三甲氧硅烷、γ-异氰酸酯丙基三乙氧基硅烷、γ-甲基丙烯酰氧丙基三甲氧基硅烷、β-(3,4-环氧环己基)乙基三甲氧基硅烷等,它们可以单独使用或者两种以上混合使用,但并不必须限定于此。本发明的光敏性树脂组合物中包含所述助粘剂时,根据需要可以适当调节其含量,例如,相对于组合物总100重量份,可以以0.1-10重量份的量包含,更具体为0.2-8重量份的量包含,进一步具体为0.4-5重量份的量包含,但并不限定于此。
所述表面活性剂起到提高光敏性树脂组合物的涂覆性或显影性的作用,其种类不受特别限定,例如,可以为氟基表面活性剂或硅表面活性剂。氟基表面活性剂的市售产品有BM-1000、BM-1100(BM Chemie公司)、Fluorad FC-135/FC-170C/FC-430(住友3M株式会社)、SH-28PA/-190/SZ-6032(Toray Silicone公司)等。硅表面活性剂的市售产品有BYK公司的BYK-310、BYK-313、BYK-320、BYK-333等,但并不必须限定于此。本发明的光敏性树脂组合物中包含所述表面活性剂时,根据需要,可以适当调节其含量,例如,相对于组合物总100重量份,可以以0.01-5重量份的量包含,更具体为0.02-4重量份的量包含,进一步具体为0.05-2重量份的量包含,但并不限定于此。
本发明的光敏性树脂组合物可以实现微细图案的同时,可以提高残膜率,从而适合形成柱状隔垫物、黑色矩阵或着色(例如,黑色)的柱状隔垫物,因此可以用于包括OLED显示器和TFT-LCD面板在内的各种电子元件。
因此,根据本发明的另一个方面,提供一种由本发明的光敏性树脂组合物形成的微细图案化固化物。
一个具体实施方案中,所述微细图案化固化物可以为柱状隔垫物、黑色矩阵或着色(例如,黑色)的柱状隔垫物。
就所述微细图案化固化物而言,例如,可以将本发明的光敏性树脂组合物涂覆在基板上后,通过图案化曝光和显影的方法形成,但并不限定于此。
以下,通过实施例对本发明进行更详细的说明。但是,本发明的范围并不限定于这些实施例。
[实施例]
制备例:粘合剂树脂的制备
将30重量份的分别以020:30:30:20的摩尔比混合甲基丙烯酸、甲基丙烯酸甲酯、甲基丙烯酸甲酯、甲基丙烯酸缩水甘油酯和丙烯酸苄酯的单体混合物、1重量份的作为热引发剂的V-65(Wako Chemical公司)、1重量份的作为用于调节分子量的链转移剂的3-巯基丙酸(3-Mercaptopropionic acid)和68重量份的作为有机溶剂的3-甲氧基丙酸甲酯加入反应容器中,然后在氮气气氛下保持65℃,搅拌8小时使聚合,从而制备作为粘合剂树脂的丙烯酸聚合物。制备的所述丙烯酸聚合物的重均分子量为25000。
实施例1至实施例5和比较例1至比较例9:光敏性树脂组合物的制备
根据下表1的组成,在设置有紫外线屏蔽膜和搅拌器的反应混合槽中添加粘合剂树脂(13重量份)、具有不饱和键的聚合性化合物(26重量份)、光聚合引发剂以及溶剂(60重量份),在常温下搅拌并混合。之后,利用尺寸为0.5微米的过滤器,对混合的溶液进行过滤,从而制备光敏性树脂组合物。
<所使用的组合物成分的说明>
粘合剂树脂:制备例中获得的丙烯酸聚合物
DPHA:双季戊四醇六丙烯酸酯(dipentaerythritol hexaacrylate)
[光引发剂A]
[光引发剂B]
[光引发剂C]
[OXE-01]
溶剂:3-甲氧基丙酸甲酯(MMP)
[表1]
将上述制备的实施例和比较例的光敏性树脂组合物分别以约1.0-15.0微米的厚度涂覆在玻璃上,然后在1.0-0.5托(torr)的低压下初步去除存在于涂覆面的溶剂,之后,在80-110℃的热板上放置约30-120秒,从而去除残留的溶剂。
曝光如上所述准备的薄膜,将曝光的薄膜用碱性水溶液(氢氧化四甲铵)显影,然后将所形成的图案在150-250℃的烘箱中加热处理30-90分钟,从而获得具有微细图案的最终固化膜。
对上述获得的实施例和比较例的各个图案,评价如下项目。
1)图案尺寸
利用SNU公司的SNU装置,测量上述制备的图案的尺寸。
2)残膜率
在上述固化膜制备方法中在不夹杂掩膜的情况下进行,计算曝光前的薄膜厚度和最终固化膜的厚度变化比例,并将其设为残膜率。
残膜率(%)=[固化后的厚度/曝光前的厚度]*100
下表2中示出上述项目的评价结果。
[表2]
从所述表2可知,比较实施例和比较例的组合物时,如图1所示,在相同的图案尺寸下,与比较例相比,实施例的组合物显示出优异的残膜率。
此外,就光引发剂C而言,与形成相同的自由基的同时目前大量使用的OXE-01(比较例7)相比,光引发剂C形成高残膜率,如图2所示,认为这是因为光引发剂C吸收I-线(I-line)的光的面积比OXE-01宽。
Claims (10)
1.一种光敏性树脂组合物,其包含:
(a)碱溶性粘合剂树脂;
(b)任意的光聚合性化合物;
(c)具有由以下化学式1表示的结构的光聚合引发剂;和
(d)有机溶剂,
基于所述(a)碱溶性粘合剂树脂和(b)任意的光聚合性化合物的总和100重量份,所述光敏性树脂组合物包含0.7-20重量份的所述(c)光聚合引发剂,
[化学式1]
所述化学式1中,R1、R2和R4-R10各自独立地表示氢、卤素、碳原子数为1-20个的直链或支链烷基、碳原子数为6-20个的芳基、碳原子数为1-20个的烷氧基、碳原子数为7-40个的芳烷基、碳原子数为1-20个的羟烷基、碳原子数为2-40个的羟基烷氧基烷基或者碳原子数为3-20个的环烷基,
R3表示碳原子数为6-20个的芳基。
2.根据权利要求1所述的光敏性树脂组合物,其中,所述碱溶性粘合剂树脂包含丙烯酸聚合物或在侧链具有丙烯酸不饱和键的丙烯酸聚合物,或者线型酚醛或双酚类型的碱溶性聚合物。
3.根据权利要求1所述的光敏性树脂组合物,其中,所述光聚合性化合物是具有至少2个以上的乙烯基双键的交联型单体。
4.根据权利要求1所述的光敏性树脂组合物,其中,R1、R2和R4-R10各自独立地表示氢、卤素、碳原子数为1-10个的直链或支链烷基、碳原子数为6-10个的芳基、碳原子数为1-10个的烷氧基、碳原子数为7-20个的芳烷基、碳原子数为1-10个的羟烷基、碳原子数为2-20个的羟基烷氧基烷基或者碳原子数为3-10个的环烷基,R3是碳原子数为6-10个的芳基。
5.根据权利要求1所述的光敏性树脂组合物,其中,所述化学式1中,R1各自独立地为氢、甲基、乙基、丙基或丁基;R2为甲基、乙基、丙基或丁基;R3为苯基;R4-R10为氢。
6.根据权利要求1所述的光敏性树脂组合物,其进一步包含链转移剂。
7.根据权利要求6所述的光敏性树脂组合物,其中,所述链转移剂选自巯基乙酸、硫代苹果酸、硫代水杨酸、2-巯基丙酸、3-巯基丙酸、3-巯基丁酸、N-(2-巯基丙酰基)甘氨酸、2-巯基烟酸、3-[N-(2-巯基乙基)氨基甲酰基]丙酸、3-[N-(2-巯基乙基)氨基]丙酸、N-(3-巯基丙酰基)丙氨酸、2-巯基乙磺酸、3-巯基丙磺酸、4-巯基丁磺酸、十二烷基(4-甲硫基)苯基醚、2-巯基乙醇、3-巯基-1,2-丙二醇、1-巯基-2-丙醇、3-巯基-2-丁醇、巯基苯酚、2-巯基乙胺、2-巯基咪唑、2-巯基苯并咪唑、2-巯基-3-吡啶酚、2-巯基苯并噻唑、巯基乙酸、三羟甲基丙烷三(3-巯基丙酸)酯、季戊四醇四(3-巯基丙酸乙酸、十二烷基硫醇、2,4-二苯基-4-甲基-1-戊烯、辛硫醇、2-巯基乙醇或它们的组合。
8.根据权利要求1所述的光敏性树脂组合物,其还包含选自着色剂、辅助固化剂、助粘剂和表面活性剂中的一种以上的成分。
9.一种固化物,其由权利要求1至8中任一项所述的光敏性树脂组合物形成。
10.根据权利要求9所述的固化物,其中,所述固化物是柱状隔垫物、黑色矩阵或着色的柱状隔垫物。
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