CN108139671A - 光敏树脂组合物及由其制备的固化膜 - Google Patents
光敏树脂组合物及由其制备的固化膜 Download PDFInfo
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- CN108139671A CN108139671A CN201680060875.8A CN201680060875A CN108139671A CN 108139671 A CN108139671 A CN 108139671A CN 201680060875 A CN201680060875 A CN 201680060875A CN 108139671 A CN108139671 A CN 108139671A
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- Prior art keywords
- resin composition
- photosensitive resin
- siloxane polymer
- cured film
- weight
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 47
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims abstract description 80
- 229920000642 polymer Polymers 0.000 claims abstract description 76
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 46
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 30
- 150000002118 epoxides Chemical class 0.000 claims abstract description 25
- 239000011737 fluorine Substances 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 18
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims abstract description 16
- -1 silane compound Chemical class 0.000 claims description 107
- 229910000077 silane Inorganic materials 0.000 claims description 43
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 239000000463 material Substances 0.000 claims description 16
- AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 16
- 229910052710 silicon Inorganic materials 0.000 claims description 15
- 238000001312 dry etching Methods 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 239000010703 silicon Substances 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000002252 acyl group Chemical group 0.000 claims description 9
- 229930195733 hydrocarbon Natural products 0.000 claims description 7
- 150000002430 hydrocarbons Chemical class 0.000 claims description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000000758 substrate Substances 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 238000000059 patterning Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 abstract description 43
- 239000000126 substance Substances 0.000 abstract description 36
- 238000004078 waterproofing Methods 0.000 abstract description 10
- 238000012805 post-processing Methods 0.000 abstract description 5
- 239000010408 film Substances 0.000 description 89
- CERQOIWHTDAKMF-UHFFFAOYSA-N alpha-methacrylic acid Natural products CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 50
- 230000015572 biosynthetic process Effects 0.000 description 38
- 238000003786 synthesis reaction Methods 0.000 description 38
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 37
- 239000002585 base Substances 0.000 description 35
- 239000002904 solvent Substances 0.000 description 27
- 239000000243 solution Substances 0.000 description 21
- 150000001875 compounds Chemical class 0.000 description 20
- 239000007787 solid Substances 0.000 description 20
- 239000004094 surface-active agent Substances 0.000 description 19
- 230000000052 comparative effect Effects 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 150000002148 esters Chemical class 0.000 description 15
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 15
- 238000002474 experimental method Methods 0.000 description 14
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 14
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 12
- TZRXHJWUDPFEEY-UHFFFAOYSA-N Pentaerythritol Tetranitrate Chemical compound [O-][N+](=O)OCC(CO[N+]([O-])=O)(CO[N+]([O-])=O)CO[N+]([O-])=O TZRXHJWUDPFEEY-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 10
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 239000003513 alkali Substances 0.000 description 8
- 150000000181 1,2-naphthoquinones Chemical class 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 238000011161 development Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000004593 Epoxy Substances 0.000 description 6
- ZZHNUBIHHLQNHX-UHFFFAOYSA-N butoxysilane Chemical class CCCCO[SiH3] ZZHNUBIHHLQNHX-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 229960004063 propylene glycol Drugs 0.000 description 6
- 235000013772 propylene glycol Nutrition 0.000 description 6
- 230000035945 sensitivity Effects 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N Vilsmeier-Haack reagent Natural products CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 239000007859 condensation product Substances 0.000 description 5
- 239000000413 hydrolysate Substances 0.000 description 5
- 230000014759 maintenance of location Effects 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 5
- 150000002989 phenols Chemical class 0.000 description 5
- 238000012545 processing Methods 0.000 description 5
- 150000004756 silanes Chemical class 0.000 description 5
- 150000004055 1,2-benzoquinones Chemical class 0.000 description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical group C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 235000006408 oxalic acid Nutrition 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- HTQNYBBTZSBWKL-UHFFFAOYSA-N 2,3,4-trihydroxbenzophenone Chemical class OC1=C(O)C(O)=CC=C1C(=O)C1=CC=CC=C1 HTQNYBBTZSBWKL-UHFFFAOYSA-N 0.000 description 3
- GWCJNVUIVCCXER-UHFFFAOYSA-N 2-(1-phenylprop-2-enoxymethyl)oxirane Chemical group C=1C=CC=CC=1C(C=C)OCC1CO1 GWCJNVUIVCCXER-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 229930185605 Bisphenol Natural products 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000001723 curing Methods 0.000 description 3
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 3
- SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical compound CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 description 3
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 3
- 238000003682 fluorination reaction Methods 0.000 description 3
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000002834 transmittance Methods 0.000 description 3
- BOVWGKNFLVZRDU-UHFFFAOYSA-N triethoxy(trifluoromethyl)silane Chemical compound CCO[Si](OCC)(OCC)C(F)(F)F BOVWGKNFLVZRDU-UHFFFAOYSA-N 0.000 description 3
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- ZAOMUMJENGCKAR-UHFFFAOYSA-N 2-(1-phenylbut-3-en-2-yloxy)but-3-enylbenzene Chemical group C=1C=CC=CC=1CC(C=C)OC(C=C)CC1=CC=CC=C1 ZAOMUMJENGCKAR-UHFFFAOYSA-N 0.000 description 2
- JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical compound OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 2
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- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
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- 229910052801 chlorine Inorganic materials 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
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Abstract
本文公开光敏树脂组合物及由其制备的固化膜。所述光敏树脂组合物向包括普通硅氧烷聚合物和环氧化合物的组合物中引入含有具有强防水性的氟原子的硅氧烷聚合物,并且氟基团可存在于所述固化膜的整个区域中,使得即使在经由干式蚀刻工艺去除所述固化膜的表面被去除之后,也可保持由于氟组分引起的所述防水性。结果,可使对后处理中使用的化学品的耐性(耐化学性)达到最大,从而提供具有优异稳定性的固化膜。
Description
技术领域
本发明涉及光敏树脂组合物及由其制备的固化膜。特定而言,本发明涉及形成高透明性和优异耐化学性的固化膜的正型光敏树脂组合物以及由所述组合物制备并且用于液晶显示器(LCD)或有机发光二极管(OLED)的固化膜。
背景技术
通常,为了绝缘的目的,在薄膜晶体管(TFT)基材上形成透明的平坦化膜,以防止LCD或OLED中的透明电极和数据线之间的接触。通过位于数据线附近的透明像素电极,面板的孔径比可增加并且可获得高亮度/分辨率。为了形成这类透明的平坦化膜,采用几个处理步骤来赋予特定的图案轮廓,并且由于需要较少的处理步骤,因此在该处理中广泛使用正型光敏树脂组合物。特别地,含有硅氧烷聚合物的正型光敏树脂组合物作为具有高耐热性、高透明性和低介电常数的材料为已知的。
负责高耐热性、高透明性和高分辨率的硅氧烷组合物在本领域中为已知的。常规的硅氧烷组合物可通过将1,2-醌二叠氮化合物加入到其中具有苯基残基的T型硅氧烷结构单元和Q型硅氧烷结构单元彼此结合的硅氧烷聚合物中而获得。举例来说,韩国特许公开专利公开第2006-59202号公开组合物,其包括含有量为20mol%或更少的酚羟基的硅氧烷聚合物、在相对于其中的酚羟基的邻位或对位中不含有甲基的醌二叠氮化合物(0.1到10wt%),以及含有醇羟基的化合物和/或含有羰基的环状化合物作为溶剂。它还公开由组合物制备的固化膜,其具有至少95%的透射率并且满足特定的色度坐标。
同时,使用含有这类硅氧烷组合物的常规正型光敏组合物制备的平坦化膜或采用其的显示装置可具有如当固化膜浸入或接触后处理中使用的溶剂、酸、碱等时膜从基材溶胀或分层的问题。此外,随着对高精度/分辨率的需求增加,并且为了减少处理时间,后处理中使用的溶剂、酸、碱等的浓度变得比以前更高。另外,固化膜的表面经由干式蚀刻工艺被去除,并且因此溶剂、酸、碱等可更容易地经由去除的表面渗透。因此,在后处理期间对可形成具有良好耐化学性的固化膜的光敏树脂组合物的需求正在增加。
发明内容
技术问题
因此,本发明的目的在于提供可形成对后处理中使用的化学材料(溶剂、酸、碱等)具有良好耐化学性的高度透明的固化膜的光敏树脂组合物,以及由其制备的用于LCD、OLED等的固化膜。
问题的解决方案
根据本发明的一个方面,提供光敏树脂组合物,其包括:
(A)含有氟原子的硅氧烷聚合物;
(B)1,2-醌二叠氮化合物;和
(C)环氧化合物。
发明的有益效果
本发明的光敏树脂组合物包含含有具有强防水性的氟原子的硅氧烷聚合物和环氧化合物。环氧化合物相对减少硅氧烷聚合物中高反应性硅烷醇基团的数量,从而改善耐化学性。同时,氟基团不仅可存在于有机膜(固化膜)的表面上,而且可存在于整个区域中,使得即使在经由干式蚀刻工艺去除固化膜的表面之后,也可保持由于氟组分引起的防水性。结果,可使对后处理中使用的化学品的耐性(耐化学性)达到最大,从而提供具有优异稳定性的固化膜。
具体实施方式
根据本发明的光敏树脂组合物包括(A)含有氟原子的硅氧烷聚合物、(B)1,2-醌二叠氮化合物和(C)环氧化合物,并且任选地还可包括(D)溶剂、(E)表面活性剂和/或(F)粘合助剂。
在下文中,将详细解释光敏树脂组合物的各组分。
在本公开中,“(甲基)丙烯酸”意指“丙烯酸”和/或“甲基丙烯酸”,“(甲基)丙烯酸酯”意指“丙烯酸酯”和/或“甲基丙烯酸酯”。
(A)含有氟原子的硅氧烷聚合物
硅氧烷聚合物包括含有氟原子的硅烷化合物和/或其水解产物的缩合物。硅氧烷聚合物只要含有氟原子就没有特别限制。氟原子可与硅氧烷聚合物的硅原子结合或可作为构成与硅原子结合的有机基团的原子被包括。有机基团可包括例如取代或未取代的氟化烃基。
氟化烃基可包括例如氟化烷基如氟甲基、氟乙基、二氟乙基、三氟甲基、三氟乙基和五氟乙基;氟化脂肪族烃如氟环戊基、二氟环戊基、四氟环戊基、九氟环戊基、四氟环己基、十一氟环己基、氟代降冰片基、二氟代降冰片基、氟代金刚烷基和二氟代金刚烷基;氟化苯基如氟苯基、二氟苯基、三氟苯基、四氟苯基和五氟苯基;氟化芳基如氟甲苯基、五氟甲苯基、三氟甲基苯基和三氟甲基氟苯基;和氟化芳烷基如氟苄基、二氟苄基、三氟苄基、四氟苄基、五氟苄基、氟苯基乙基和五氟苯基乙基。
在这些基团中,氟化烷基为优选的,并且三氟甲基、三氟乙基和五氟乙基为更优选的。
可取代氟化烃的取代基可包括例如卤素原子如氯原子、溴原子和碘原子、羟基、烷氧基、烷氧基羰基、烷氧基羰氧基、酰基、酰氧基、氰基等。
含有氟原子的硅氧烷聚合物(A)可包括至少一种衍生自由下式1表示的硅烷化合物的结构单元:
[式1]
(R1)nSi(OR2)4-n
在式1中,R1为氟原子或含有氟原子的一价烃,其中在R1为一价烃的情况下,氢原子可部分或全部被取代,并且在同一分子中存在多个R1的情况下,每个R1可彼此相同或不同;
R2为氢、具有1到6个碳原子的烷基、具有2到6个碳原子的酰基或具有6到15个碳原子的芳基,其中在同一分子中存在多个R2的情况下,每个R2可彼此相同或不同,并且在R2为烷基、酰基或芳基的情况下,氢原子可部分或全部被取代;和
n为1到3的整数。
硅烷化合物的具体实例可包括氟三甲氧基硅烷、氟三乙氧基硅烷、三氟甲基三甲氧基硅烷、三氟甲基三乙氧基硅烷、三氟丙基三甲氧基硅烷、三氟丙基三乙氧基硅烷、氟甲基二甲氧基硅烷、氟甲基二乙氧基硅烷、三氟甲基二甲氧基硅烷、三氟甲基二乙氧基硅烷、三氟丙基甲基二甲氧基硅烷、三氟丙基甲基二乙氧基硅烷、氟苯基三甲氧基硅烷、氟苯基三乙氧基硅烷、三氟乙基三甲氧基硅烷、三氟乙基三乙氧基硅烷、五氟乙基三甲氧基硅烷、五氟乙基三乙氧基硅烷等。化合物可单独使用或以两种或更多种的组合形式使用。
在这些化合物中,含有氟化烷基的硅烷化合物为优选的。具体而言,更优选三氟甲基三甲氧基硅烷、三氟甲基三乙氧基硅烷、三氟乙基三甲氧基硅烷、三氟乙基三乙氧基硅烷、五氟乙基三甲氧基硅烷或五氟乙基三乙氧基硅烷,并且特别优选三氟甲基三甲氧基硅烷或三氟甲基三乙氧基硅烷。
含有氟原子的硅氧烷聚合物(A)还可包括至少一种衍生自由下式2表示的硅烷化合物的结构单元:
[式2]
(R3)nSi(OR4)4-n
在式2中,R3为具有1到12个碳原子的烷基、具有2到10个碳原子的烯基或具有6到15个碳原子的芳基,其中在同一分子中存在多个R3的情况下,每个R3可彼此相同或不同,并且在R3为烷基、烯基或芳基的情况下,氢原子可部分或全部被取代,并且R3可包括含有杂原子的结构单元;
R4为氢、具有1到6个碳原子的烷基、具有2到6个碳原子的酰基或具有6到15个碳原子的芳基,其中在同一分子中存在多个R4的情况下,每个R4可彼此相同或不同,并且在R4为烷基、酰基或芳基的情况下,氢原子可部分或全部被取代;和
n为0到3的整数。
包括含有杂原子的结构单元的R3的实例可包括醚、酯和硫化物。
硅烷化合物可为其中n为0的四官能硅烷化合物、其中n为1的三官能硅烷化合物、其中n为2的双官能硅烷化合物和其中n为3的单官能硅烷化合物。
特别地,含有氟原子的硅氧烷聚合物可包括衍生自其中n为0的式2的硅烷化合物的结构单元。
由式2表示的硅烷化合物的具体实例可包括,例如,作为四官能硅烷化合物的四乙酰氧基硅烷、四甲氧基硅烷、四乙氧基硅烷、四丁氧基硅烷、四苯氧基硅烷、四苄氧基硅烷和四丙氧基硅烷;作为三官能硅烷化合物的甲基三甲氧基硅烷、甲基三乙氧基硅烷、甲基三异丙氧基硅烷、甲基三丁氧基硅烷、乙基三甲氧基硅烷、乙基三乙氧基硅烷、乙基三异丙氧基硅烷、乙基三丁氧基硅烷、丁基三甲氧基硅烷、苯基三甲氧基硅烷、苯基三乙氧基硅烷、d3-甲基三甲氧基硅烷、n-丙基三甲氧基硅烷、n-丙基三乙氧基硅烷、n-丁基三乙氧基硅烷、n-己基三甲氧基硅烷、n-己基三乙氧基硅烷、癸基三甲氧基硅烷、乙烯基三甲氧基硅烷、乙烯基三乙氧基硅烷、3-甲基丙烯酰氧基丙基三甲氧基硅烷、3-甲基丙烯酰氧基丙基三乙氧基硅烷、3-丙烯酰氧基丙基三甲氧基硅烷、3-丙烯酰氧基丙基三乙氧基硅烷、对羟基苯基三甲氧基硅烷、1-(对羟基苯基)乙基三甲氧基硅烷、2-(对羟基苯基)乙基三甲氧基硅烷、4-羟基-5-(对羟基苯基羰氧基)戊基三甲氧基硅烷、3-氨基丙基三甲氧基硅烷、3-氨基丙基三乙氧基硅烷、3-缩水甘油氧基丙基三甲氧基硅烷、3-缩水甘油氧基丙基三乙氧基硅烷、2-(3,4-环氧环己基)乙基三甲氧基硅烷、2-(3,4-环氧环己基)乙基三乙氧基硅烷、[(3-乙基-3-氧杂环丁烷基)甲氧基]丙基三甲氧基硅烷、[(3-乙基-3-氧杂环丁烷基)甲氧基]丙基三乙氧基硅烷、3-巯基丙基三甲氧基硅烷和3-三甲氧基硅烷基丙基琥珀酸;作为二官能硅烷化合物的二甲基二乙酰氧基硅烷、二甲基二甲氧基硅烷、二苯基二甲氧基硅烷、二苯基二乙氧基硅烷、二苯基二苯氧基硅烷、二丁基二甲氧基硅烷、二甲基二乙氧基硅烷、(3-缩水甘油氧基丙基)甲基二甲氧基硅烷、(3-缩水甘油氧基丙基)甲基二乙氧基硅烷、3-(2-氨基乙基氨基)丙基二甲氧基甲基硅烷、3-氨基丙基二乙氧基甲基硅烷、3-氯丙基二甲氧基甲基硅烷、3-巯基丙基二甲氧基甲基硅烷、环己基二甲氧基甲基硅烷、二乙氧基甲基乙烯基硅烷、二甲氧基甲基乙烯基硅烷和二甲氧基二-对甲苯基硅烷;和作为单官能硅烷化合物的三甲基硅烷、三丁基硅烷、三甲基甲氧基硅烷、三丁基乙氧基硅烷、(3-缩水甘油氧基丙基)二甲基甲氧基硅烷和(3-缩水甘油氧基丙基)二甲基乙氧基硅烷。
在四官能硅烷化合物中优选四甲氧基硅烷、四乙氧基硅烷和四丁氧基硅烷;在三官能硅烷化合物中优选甲基三甲氧基硅烷、甲基三乙氧基硅烷、甲基三异丙氧基硅烷、甲基三丁氧基硅烷、苯基三甲氧基硅烷、乙基三甲氧基硅烷、乙基三乙氧基硅烷、乙基三异丙氧基硅烷、乙基三丁氧基硅烷和丁基三甲氧基硅烷;在二官能硅烷化合物中优选二甲基二甲氧基硅烷、二苯基二甲氧基硅烷、二苯基二乙氧基硅烷、二苯基二苯氧基硅烷、二丁基二甲氧基硅烷和二甲基二乙氧基硅烷。
这些硅烷化合物可单独使用或以其两种或更多种的组合形式使用。
含有氟原子的硅氧烷聚合物(A)可为式1的硅烷化合物或其水解产物与式2的硅烷化合物或其水解产物的缩合物。
用于制备由式1或2表示的硅烷化合物或其缩合物的水解产物的条件没有特别限制。举例来说,期望水解产物或其缩合物可通过以下制备:将式1或2的硅烷化合物在如乙醇、2-丙醇、丙酮和乙酸丁酯的溶剂中稀释;向其中加入反应所需的水,并且将作为催化剂的酸(例如盐酸、乙酸、硝酸等)或碱(例如氨、三乙胺、环己胺、氢氧化四甲基铵等);并且然后搅拌由此获得的混合物以完成水解聚合反应。
含有氟原子的硅氧烷聚合物的重均分子量优选在500到50,000的范围内。在此范围内,光敏树脂组合物可具有期望的成膜性、溶解性和显影剂中的溶解速率。
制备中使用的溶剂和酸或碱催化剂的种类及其量可任选地选择而没有特别限制。水解聚合可在20℃或更低的低温下进行,但反应也可通过加热或回流来促进。反应所需的时间可根据包括硅烷单体的种类或浓度、反应温度等的各种条件而变化。通常,获得具有约500的50,000的重均分子量的缩合物所需的反应时间在15分钟到30天的范围内;然而,反应时间不限于此。
基于Si原子摩尔数,含有氟原子的硅氧烷聚合物中的氟原子含量可为在硅氧烷聚合物中的含氟结构单元的含量(摩尔%)的1到30%、1到20%或2到20%。在该范围内,由此制造的固化膜可包括在包括其表面的整个固化膜上具有强防水性的氟组分,并且即使在通过化学处理如干式蚀刻去除固化膜的表面之后也可保持防水性,从而使耐化学性达到最大。然而,如果氟原子含量偏离该范围,那么过量的氟组分可彼此结合以相当弱的耐化学性。
硅氧烷聚合物(A)可包括线性硅氧烷结构单元(即,D型硅氧烷结构单元)。线性硅氧烷结构单元可衍生自双官能硅烷化合物,例如由其中n为2的式2表示的硅烷化合物。具体而言,硅氧烷聚合物(A)包括衍生自其中n为2的式2的硅烷化合物的结构单元,基于Si原子摩尔数,其量为0.5到50摩尔%,并且优选1到30摩尔%。在此范围内,固化膜可保持恒定的硬度,并且表现出柔性,从而进一步改善对外部应力的抗裂性。
此外,硅氧烷聚合物(A)可包括衍生自由其中n为1的式2表示的硅烷化合物的结构单元(即,T型结构单元)。优选地,基于Si原子摩尔数,硅氧烷聚合物(A)包括衍生自由其中n为1的式2表示的量为40到85摩尔%,更优选50到80摩尔%的硅烷化合物的结构单元。在此范围内,光敏树脂组合物可形成具有更精确图案轮廓的固化膜。
另外,考虑到固化膜的硬度、感光度和保留率,硅氧烷聚合物(A)优选包括衍生自具有芳基的硅烷化合物的结构单元。举例来说,基于Si原子摩尔数,硅氧烷聚合物(A)可包括衍生自具有30到70摩尔%,并且优选35到50摩尔%的量的芳基的硅烷化合物的结构单元。在此范围内,硅氧烷聚合物与1,2-萘醌二叠氮化合物的相容性良好,并且因此可防止感光度的过度降低,同时获得固化膜的更有利的透明性。衍生自具有芳基的硅烷化合物的结构单元可为衍生自式2的硅烷化合物的结构单元,其中R3为芳基,特别为衍生自式2的硅烷化合物,其中n为1并且R3为芳基,更特别地,衍生自式2的硅烷化合物,其中n为1并且R3为苯基(即,T-苯基型结构单元)。
硅氧烷聚合物(A)可包括衍生自由其中n为0的式2表示的硅烷化合物的结构单元(即,Q型结构单元)。优选地,基于Si原子摩尔数,硅氧烷聚合物(A)包括衍生自由其中n为0的式2表示的量为10到40摩尔%,并且优选15到35摩尔%的硅烷化合物的结构单元。在此范围内,光敏树脂组合物可在形成图案期间以适当的程度保持其在碱性水溶液中的溶解度,从而防止由溶解度降低或组合物的溶解度急剧增加而引起的任何缺陷。
如本文所用的术语“基于Si原子摩尔数的摩尔%”是指特定结构单元中所含的Si原子的摩尔数相对于构成硅氧烷聚合物的全部结构单元中所含的Si原子的总摩尔数的百分比。
硅氧烷聚合物(A)中硅氧烷单元的摩尔量可通过Si-NMR、1H-NMR、13C-NMR、IR、TOF-MS、元素分析、灰分测定等的组合来测量。举例来说,为了测量具有苯基的硅氧烷单元的摩尔量,对全部硅氧烷聚合物执行Si-NMR分析,然后分析苯基结合的Si峰面积和苯基未结合的Si峰面积并且因此可从它们之间的峰面积比计算摩尔量。
基于不包括溶剂的组合物的固体含量的总重量,本发明的光敏树脂组合物可包括含有50到95重量%,并且优选65到90重量%的量的氟原子的硅氧烷聚合物(A)。在此量范围内,树脂组合物可将其显影性保持在合适的水平,从而生产具有改善的膜保留率和图案分辨率的固化膜。
(B)1,2-醌二叠氮化合物
根据本发明的光敏树脂组合物包括1,2-醌二叠氮化合物(B)。
1,2-醌二叠氮化合物可为在光刻胶领域中用作光敏剂的任何化合物。
1,2-醌二叠氮化合物的实例包括酚化合物与1,2-苯醌二叠氮-4-磺酸或1,2-苯醌二叠氮-5-磺酸的酯;酚化合物与1,2-萘醌二叠氮-4-磺酸或1,2-萘醌二叠氮-5-磺酸的酯;其中羟基被氨基取代的酚化合物与1,2-苯醌二叠氮-4-磺酸或1,2-苯醌二叠氮-5-磺酸的磺酰胺;和其中羟基被氨基取代的酚化合物与1,2-萘醌二叠氮-4-磺酸或1,2-萘醌二叠氮-5-磺酸的磺酰胺。以上化合物可单独使用或以两种或更多种化合物的组合形式使用。
酚化合物的实例包括2,3,4-三羟基二苯甲酮、2,4,6-三羟基二苯甲酮、2,2′,4,4′-四羟基二苯甲酮、2,3,3′,4-四羟基二苯甲酮、2,3,4,4′-四羟基二苯甲酮、双(2,4-二羟基苯基)甲烷、双(对羟基苯基)甲烷、三(对羟基苯基)甲烷、1,1,1-三(对羟基苯基)乙烷、双(2,3,4-三羟基苯基)甲烷、2,2-双(2,3,4-三羟基苯基)丙烷、1,1,3-三(2,5-二甲基-4-羟基苯基)-3-苯基丙烷、4,4′-[1-[4-[1-[4-羟基苯基]-1-甲基乙基]苯基]亚乙基]双酚、双(2,5-二甲基-4-羟基苯基)-2-羟基苯基甲烷、3,3,3′,3′-四甲基-1,1′-螺二茚-5,6,7,5′,6′,7′-己醇和2,2,4-三甲基-7,2′,4′-三羟基黄烷。
1,2-醌二叠氮化合物的更具体实例包括2,3,4-三羟基二苯甲酮和1,2-萘醌二叠氮-4-磺酸的酯、2,3,4-三羟基二苯甲酮和1,2-萘醌二叠氮-5-磺酸的酯、4,4′-[1-[4-[1-[4-羟基苯基]-1-甲基乙基]苯基]亚乙基]双酚和1,2-萘醌二叠氮-4-磺酸的酯,和4,4′-[1-[4-[1-[4-羟基苯基]-1-甲基乙基]苯基]亚乙基]双酚和1,2-萘醌二叠氮-5-磺酸的酯。
以上化合物可单独使用或以两种或更多种化合物的组合形式使用。
通过使用上述优选的化合物,可改善正型光敏树脂组合物的透明性。
以不包括溶剂的固体含量为基准基于100重量份的硅氧烷聚合物(A),1,2-醌二叠氮化合物(B)可以1到50重量份,优选2到25重量份,并且更优选3到15重量份的量包括在光敏树脂组合物中。当1,2-醌二叠氮化合物以上述量的范围使用时,树脂组合物可更容易地形成图案,同时抑制在显影时在图案的底部处产生缺陷,如涂布膜的粗糙表面和浮渣。
(C)环氧化合物
在本发明的光敏树脂组合物中,环氧化合物与硅氧烷聚合物一起采用以便增加硅氧烷粘结剂的内部密度,以从而改善由其制备的固化膜的耐化学性。
环氧化合物可为包括至少一个环氧基团的不饱和单体的均低聚物或异低聚物。
包括至少一个环氧基团的不饱和单体的实例可包括(甲基)丙烯酸缩水甘油酯、丙烯酸4-羟基丁酯缩水甘油醚、(甲基)丙烯酸3,4-环氧丁酯、(甲基)丙烯酸4,5-环氧戊酯、(甲基)丙烯酸5,6-环氧己基、(甲基)丙烯酸6,7-环氧庚酯、(甲基)丙烯酸2,3-环氧环戊酯、(甲基)丙烯酸3,4-环氧环己酯、丙烯酸α-乙基缩水甘油酯、丙烯酸α-正丙基缩水甘油酯、丙烯酸α-正丁基缩水甘油酯、N-(4-(2,3-环氧丙氧基)-3,5-二甲基苄基)丙烯酰胺、N-(4-(2,3-环氧丙氧基)-3,5-二甲基苯基丙基)丙烯酰胺、烯丙基缩水甘油醚、2-甲基烯丙基缩水甘油醚、邻乙烯基苄基缩水甘油醚、间乙烯基苄基缩水甘油醚、对乙烯基苄基缩水甘油醚或它们的混合物。优选地,可使用甲基丙烯酸缩水甘油酯。
环氧化合物可通过本领域已知的任何常规方法合成。
市售环氧化合物的实例可包括GHP03(甲基丙烯酸缩水甘油酯均聚物,美源商事株式会社(Miwon Commercial Co.,Ltd.))。
环氧化合物(C)可进一步包括以下结构单元。
代表性实例可包括衍生自以下的任何结构单元:苯乙烯;具有烷基取代基的苯乙烯,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、庚基苯乙烯和辛基苯乙烯;具有卤素的苯乙烯,如氟苯乙烯、氯苯乙烯、溴苯乙烯和碘苯乙烯;具有烷氧基取代基的苯乙烯,如甲氧基苯乙烯、乙氧基苯乙烯和丙氧基苯乙烯;对羟基-α-甲基苯乙烯、乙酰苯乙烯;具有芳香环的烯属不饱和化合物,如二乙烯基苯、乙烯基苯酚、邻乙烯基苄基甲醚、间乙烯基苄基甲醚和对乙烯基苄基甲醚;不饱和羧酸制,如(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸丁酯、(甲基)丙烯酸二甲氨基乙酯、(甲基)丙烯酸异丁酯、(甲基)丙烯酸叔丁酯、(甲基)丙烯酸环己酯、(甲基)丙烯酸乙基己酯、(甲基)丙烯酸四氢糠酯、(甲基)丙烯酸羟乙酯、(甲基)丙烯酸2-羟丙酯、(甲基)丙烯酸2-羟基-3-氯丙酯、(甲基)丙烯酸4-羟丁酯、(甲基)丙烯酸甘油酯、α-羟基甲基丙烯酸甲酯、α-羟基甲基丙烯酸乙酯、α-羟基甲基丙烯酸丙酯、α-羟基甲基丙烯酸丁酯、(甲基)丙烯酸2-甲氧基乙酯、(甲基)丙烯酸3-甲氧基丁酯、(甲基)丙烯酸乙氧基二甘醇酯、(甲基)丙烯酸甲氧基三乙二醇酯、(甲基)丙烯酸甲氧基三丙二醇酯、聚(乙二醇)甲醚(甲基)丙烯酸酯、(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、(甲基)丙烯酸苯氧基二甘醇酯、(甲基)丙烯酸对壬基苯氧基聚乙二醇酯、(甲基)丙烯酸对壬基苯氧基聚丙二醇酯、(甲基)丙烯酸四氟丙酯、(甲基)丙烯酸1,1,1,3,3,3-六氟异丙酯、(甲基)丙烯酸八氟戊酯、(甲基)丙烯酸十七氟癸酯、(甲基)丙烯酸三溴苯酯、(甲基)丙烯酸异冰片酯、(甲基)丙烯酸二环戊酯、(甲基)丙烯酸二环戊烯酯、(甲基)丙烯酸二环戊氧基乙酯和(甲基)丙烯酸二环戊烯氧基乙酯;具有N-乙烯基的叔胺,如N-乙烯基吡咯烷酮、N-乙烯基咔唑和N-乙烯基吗啉;不饱和醚,如乙烯基甲醚和乙烯基乙醚;不饱和酰亚胺,如N-苯基马来酰亚胺、N-(4-氯苯基)马来酰亚胺、N-(4-羟基苯基)马来酰亚胺和N-环己基马来酰亚胺。衍生自上述示例性化合物的结构单元可单独包含在环氧化合物(C)中或包含其两种或更多种的组合。
为了组合物的聚合性,在这些实例中优选苯乙烯类化合物。
特别地,从耐化学性的观点出发,更优选在这些化合物中通过不使用衍生自含有羧基的单体的结构单元而使环氧化合物(C)不含羧基。
基于构成环氧化合物(C)的结构单元的总摩尔数,结构单元可以0到70摩尔%,优选10到60摩尔%的量使用。在此范围内,固化膜可具有期望硬度。
环氧化合物(C)的重均分子量可在100到30,000,并且优选1,000到15,000的范围内。如果环氧化合物的重均分子量为至少100,那么固化膜可具有改善的硬度。此外,如果环氧化合物的重均分子量为30,000或更少,那么固化膜可具有均匀厚度,这适合于使其上的任何步骤平坦化。通过使用聚苯乙烯标准物的凝胶渗透色谱法(GPC,洗脱液:四氢呋喃)测定重均分子量。
在本发明的光敏树脂组合物中,以不包括溶剂的固体含量为基准基于100重量份的硅氧烷聚合物(A),环氧化合物(C)可以0.5到50重量份,优选1到30重量份,并且更优选5到25重量份的量包括在光敏树脂组合物中。在所述量范围内,可改善光敏树脂组合物的耐化学性和感光度。如果所述量范围偏离所述范围,那么使用少量时耐化学性可大大劣化,并且使用过量时感光度可大大劣化。
(D)溶剂
本发明的光敏树脂组合物可制备成其中上述组分与溶剂混合的液体组合物。溶剂可为例如有机溶剂。
根据本发明的光敏树脂组合物中的溶剂的量没有特别限制。举例来说,光敏树脂组合物可含有一定量的溶剂,使得其固体含量范围基于光敏树脂组合物的总重量为5到80重量%,优选10到70重量%,并且更优选15到60重量%。固体含量是指不包括溶剂的本发明的树脂组合物中包括的全部组分。在所述量范围内,可涂布性可为有利的,并且可保持适当程度的流动性。
本发明的溶剂只要能够溶解组合物的各组分并且化学稳定就没有特别限制。溶剂的实例可包括醇、醚、乙二醇醚、乙二醇烷基醚乙酸酯、二甘醇、丙二醇单烷基醚、丙二醇烷基醚乙酸酯、丙二醇烷基醚丙酸酯、芳香烃、酮、酯等。
溶剂的具体实例包括甲醇、乙醇、四氢呋喃、二恶烷、甲基溶纤剂乙酸酯、乙基溶纤剂乙酸酯、乙酰乙酸乙酯、乙二醇单甲醚、乙二醇单乙醚、乙二醇二甲醚、乙二醇二乙醚、丙二醇二甲醚、丙二醇二乙醚、二甘醇单甲醚、二甘醇单乙醚、二甘醇二甲醚、二甘醇乙基甲醚、丙二醇单甲醚、丙二醇单乙醚、丙二醇单丙醚、二丙二醇二甲醚、二丙二醇二乙醚、丙二醇甲醚乙酸酯、丙二醇乙醚乙酸酯、丙二醇丙醚乙酸酯、二丙二醇甲醚乙酸酯、丙二醇丁醚乙酸酯、甲苯、二甲苯、甲乙酮、4-羟基-4-甲基-2-戊酮、环戊酮、环己酮、2-庚酮、γ-丁内酯、2-羟基丙酸乙酯、2-羟基-2-甲基丙酸乙酯、乙氧基乙酸乙酯、羟基乙酸乙酯、2-羟基-3-甲基丁酸甲酯、2-甲氧基丙酸甲酯、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、丙酮酸甲酯、丙酮酸乙酯、乙酸乙酯、乙酸丁酯、乳酸乙酯、乳酸丁酯、N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基吡咯烷酮等。
在这些示例性溶剂中优选乙二醇烷基醚乙酸酯、二甘醇、丙二醇单烷基醚、丙二醇烷基醚乙酸酯和酮。特别地,优选二甘醇二甲醚、二甘醇乙基甲醚、二丙二醇二甲醚、二丙二醇二乙醚、丙二醇单甲醚、丙二醇单乙醚、丙二醇甲醚乙酸酯、2-甲氧基丙酸甲酯、γ-丁内酯和4-羟基-4-甲基-2-戊酮为优选的。
以上化合物可单独使用或以其两种或更多种的组合形式使用。
(E)表面活性剂
本发明的光敏树脂组合物可进一步包括表面活性剂以增强其可涂布性。
表面活性剂的种类不受限制,但优选氟类表面活性剂、硅类表面活性剂、非离子表面活性剂等。
表面活性剂的具体实例可包括基于氟和硅类表面活性剂,如由道康宁东丽有机硅株式会社(Dow Corning Toray Silicon Co.,Ltd.)制造的FZ-2122,由博多默勒化工株式会社(BM CHEMIE Co.,Ltd.)制造的BM-1000和BM-1100,由大日本油墨化学工业株式会社(Dai Nippon Ink Kagaku Kogyo Co.,Ltd.)制造的Megapack F-142D、Megapack F-172、Megapack F-173和Megapack F-183,由住友3M株式会社(Sumitomo 3M Ltd.)制造的FloradFC-135、Florad FC-170C、Florad FC-430和Florad FC-431,由旭硝子株式会社(AsahiGlass Co.,Ltd.)制造的Sufron S-112、Sufron S-113、Sufron S-131、Sufron S-141、Sufron S-145、Sufron S-382、Sufron SC-101、Sufron SC-102、Sufron SC-103、SufronSC-104、Sufron SC-105和Sufron SC-106,由Shinakida Kasei Co.,Ltd.制造的EftopEF301、Eftop EF303和Eftop EF352,由道康宁东丽有机硅株式会社制造的SH-28PA、SH-190、SH-193、SZ-6032、SF-8428、DC-57和DC-190;非离子表面活性剂如包括聚氧乙烯月桂基醚、聚氧乙烯硬脂基醚、聚氧乙烯油烯基醚等的聚氧乙烯烷基醚类,包括聚氧乙烯辛基苯基醚、聚氧乙烯壬基苯基醚等的聚氧乙烯芳基醚类,和包括聚氧乙烯二月桂酸酯、聚氧乙烯二硬脂酸酯等的聚氧乙烯二烷基酯类;和有机硅氧烷聚合物KP341(由信越化学工业株式会社(Shin-Etsu Chemical Co.,Ltd.)制造)、(甲基)丙烯酸酯类共聚物Polyflow No.57和95(共荣社化学株式会社(Kyoeisha Yuji Chemical Co.,Ltd.))等。表面活性剂可单独使用或以其两种或更多种的组合形式使用。
以不包括溶剂的固体含量为基准基于100重量份的硅氧烷聚合物(A),表面活性剂(E)可以0.001到5重量份,优选0.05到3重量份,并且更优选0.2到2重量份的量包含在光敏树脂组合物中。在所述量范围内,组合物的可涂布性和流平性可为良好的。
本发明的光敏树脂组合物可用作正型光敏树脂组合物。
特别地,由于本发明的光敏树脂组合物将包含具有强防水性的氟原子的硅氧烷聚合物引入到包括普通硅氧烷聚合物和环氧化合物的组合物中,所以环氧化合物相对减少高反应性硅烷醇基团在硅氧烷聚合物中的数量,从而改善耐化学性。同时,氟基团不仅可存在于有机膜(固化膜)的表面上,而且可存在于整个区域中,使得即使在经由干式蚀刻工艺去除固化膜的表面之后,也可保持由于氟组分引起的防水性。结果,可使对后处理中使用的化学品的耐性(耐化学性)达到最大,从而提供具有优异稳定性的固化膜。
此外,本发明提供由光敏树脂组合物制备的固化膜。
可通过本领域已知的方法制备固化膜,例如通过将光敏树脂组合物涂布在基材上并且使所得组合物经历固化工艺。
涂布工艺可通过旋涂法、缝涂法、辊涂法、丝网印刷法、涂布器法等进行至例如2到25μm的期望厚度。
为了固化光敏树脂组合物,例如,涂布在基材上的组合物可在例如60到130℃的温度下经历预烘烤以去除溶剂;然后使用具有期望图案的光掩模曝光;并且使用显影剂(例如四甲基氢氧化铵(TMAH)溶液)经历显影以在涂布膜上形成图案。曝光可在200到500nm的波段中以365nm的波长为基准,以10到200mJ/cm2的曝光量进行。作为用于曝光(照射)的光源,可使用低压水银灯、高压水银灯、超高压水银灯、金属卤化物灯、氩气激光器等;并且如果需要,还可使用X射线、电子射线等。
然后,将具有图案的涂布膜经历后烘烤,在必要时,例如在150到300℃的温度下后烘烤10分钟到5小时,以制备期望的固化膜。
另外,本发明提供形成图案的方法,包括使用光敏树脂组合物在基材的表面上形成含硅膜;使用光图案化含硅膜;以及干式蚀刻图案化的含硅膜和基材以在基材上形成图案。
具体而言,可通过包括以下的工艺来形成图案化的含硅膜:将光敏树脂组合物涂布在基材的表面上、曝光和显影。通过对图案化的含硅膜和基材进行干式蚀刻,可在基材上形成图案。
通过方法形成的含硅固化膜在干式蚀刻后可具有80°或更大的接触角。
如此图案化的固化膜在耐热性、透明性、介电常数、耐溶剂性、耐酸性和耐碱性方面具有优异的物理性质。
如此图案化的固化膜在组合物经受热处理或浸渍于溶剂、酸、碱等中或与溶剂、酸、碱等接触时,具有优异的透光率而没有表面粗糙。因此,可有效地使用固化膜作为用于LCD或OLED的TFT基材的平坦化膜;OLED的分区;半导体器件的层间电介质;光波导的芯或包层材料等。
此外,本发明提供包括图案化的固化膜作为保护膜的电子部件。
本发明的模式
在下文中,将参考以下实例更详细地描述本发明。然而,提供这些实例仅用于说明本发明,并且本发明的范围不限于此。
在以下实例中,通过使用聚苯乙烯标准物的凝胶渗透色谱法(GPC)测定重均分子量。
合成例1:硅氧烷聚合物(a)的合成
向配备有回流冷凝器的反应器中加入40重量%苯基三甲氧基硅烷、15重量%甲基三甲氧基硅烷、20重量%四乙氧基硅烷和20重量%纯水,并且然后加入5重量%丙二醇单甲醚乙酸酯(PGMEA),随后在0.1重量%草酸催化剂存在下回流并且搅拌混合物7小时,并且然后冷却。之后,将反应产物用PGMEA稀释使得固体含量为40重量%。合成具有约5,000到10,000Da的重均分子量的硅氧烷聚合物。
合成例2:硅氧烷聚合物(b)的合成
向配备有回流冷凝器的反应器中加入20重量%苯基三甲氧基硅烷、30重量%甲基三甲氧基硅烷、20重量%四乙氧基硅烷和15重量%纯水,并且然后加入15重量%PGMEA,随后在0.1重量%草酸催化剂存在下回流并且搅拌混合物6小时,并且然后冷却。之后,将反应产物用PGMEA稀释使得固体含量为30重量%。合成具有约8,000到13,000Da的重均分子量的硅氧烷聚合物。
合成例3:硅氧烷聚合物(c)的合成
向配备有回流冷凝器的反应器中加入20重量%苯基三甲氧基硅烷、30重量%甲基三甲氧基硅烷、20重量%四乙氧基硅烷和15重量%纯水,并且然后加入15重量%PGMEA,随后在0.1重量%草酸催化剂存在下回流并且搅拌混合物5小时,并且然后冷却。之后,将反应产物用PGMEA稀释使得固体含量为30重量%。合成具有约9,000到15,000Da的重均分子量的硅氧烷聚合物。
合成例4:含有氟的硅氧烷聚合物(d)的合成
向配备有回流冷凝器的反应器中加入30重量%苯基三甲氧基硅烷、15重量%甲基三甲氧基硅烷、20重量%四乙氧基硅烷、10重量%三氟丙基三甲氧基硅烷和20重量%纯水,并且然后加入5重量%PGMEA,随后在0.1重量%草酸催化剂存在下回流并且搅拌混合物7小时,并且然后冷却。之后,将反应产物用PGMEA稀释使得固体含量为40重量%。合成具有约5,000到10,000Da的重均分子量的含有氟的硅氧烷聚合物。
合成例5:环氧化合物的合成
将配备有冷凝器的三颈烧瓶放置在具有自动温度控制器的搅拌器上。将100重量份由甲基丙烯酸缩水甘油酯(100摩尔%)组成的单体、10重量份2,2′-偶氮双(2-甲基丁腈)和100重量份PGMEA放入烧瓶中,并且烧瓶充满氮气。在缓慢搅拌混合物的情况下,将烧瓶加热至80℃,并且温度保持5小时,以获得具有约6,000到10,000Da的重均分子量的环氧化合物。然后,向其中加入PGMEA,将其固体含量调整为20重量%。
实例和比较例:光敏树脂组合物的制备
使用以上合成例中获得的化合物制备以下实例和比较例的光敏树脂组合物。
此外,在实例和比较例中使用下列化合物:
-1,2-醌二叠氮化合物:MIPHOTO TPA-517,美源商事株式会社
-溶剂:PGMEA,Chemtronics Co.,Ltd.
γ-丁内酯(GBL),巴斯夫(BASF)
-表面活性剂:硅表面活性剂,FZ-2122,道康宁东丽株式会社(Dow Corning TorayCo.,Ltd.)
:氟表面活性剂,TF-1831,大日本油墨化学工业(DIC)
:氟表面活性剂,RS-932,大日本油墨化学工业
:氟表面活性剂,TF-1807,大日本油墨化学工业
实例1:将25.9重量份合成例1的硅氧烷聚合物(a)的溶液、34.4重量份合成例2的硅氧烷聚合物(b)的溶液、34.2重量份合成例3的硅氧烷聚合物(c)的溶液和5.5重量份合成例4的硅氧烷聚合物(d)的溶液混合,并且然后将5.5重量份TPA-517作为1,2-醌二叠氮化合物、22.1重量份合成例5的环氧化合物和1.1重量份FZ-2122作为表面活性剂(基于100重量份全部硅氧烷聚合物)均匀地混合。将混合物溶解在PGMEA和GBL(PGMEA∶GBL=88∶12重量比)的混合物中,使得固体含量为17%。将混合物搅拌1小时30分钟,并且使用具有0.2μm孔的膜过滤器过滤以获得具有17重量%固体含量的组合物。
实例2:除了使用24.2重量份合成例1的硅氧烷聚合物(a)的溶液、32.1重量份合成例2的硅氧烷聚合物(b)的溶液、32.6重量份合成例3的硅氧烷聚合物(c)的溶液和11.1重量份合成例4的硅氧烷聚合物(d)的溶液作为硅氧烷聚合物,并且使用21.3重量份合成例5的环氧化合物以外,通过进行与实例1中所述相同的程序获得固体含量为17重量%的组合物。
实例3:除了使用22.6重量份合成例1的硅氧烷聚合物(a)的溶液、30.0重量份合成例2的硅氧烷聚合物(b)的溶液、30.8重量份合成例3的硅氧烷聚合物(c)的溶液和16.6重量份合成例4的硅氧烷聚合物(d)的溶液作为硅氧烷聚合物,并且使用19.8重量份合成例5的环氧化合物以外,通过进行与实例1中所述相同的程序获得固体含量为17重量%的组合物。
实例4:除了使用20.6重量份合成例1的硅氧烷聚合物(a)的溶液,27.4重量份合成例2的硅氧烷聚合物(b)的溶液、29.8重量份合成例3的硅氧烷聚合物(c)的溶液和22.3重量份合成例4的硅氧烷聚合物(d)的溶液作为硅氧烷聚合物,并且使用19.3重量份合成例5的环氧化合物以外,通过进行与实例1中所述相同的程序获得固体含量为17重量%的组合物。
比较例1:除了使用27.4重量份合成例1的硅氧烷聚合物(a)的溶液、36.3重量份合成例2的硅氧烷聚合物(b)的溶液和36.3重量份合成例3的硅氧烷聚合物(c)的溶液作为硅氧烷聚合物,并且使用23.6重量份合成例5的环氧化合物以外,通过进行与实例1中所述相同的程序获得固体含量为17重量%的组合物。
比较例2:除了使用5.6重量份TPA-517作为1,2-醌二叠氮化合物以及0.5重量份TF-1831和1.1重量份FZ-2122作为表面活性剂以外,通过进行与比较例1中所述相同的程序获得固体含量为17重量%的组合物。
比较例3:除了使用5.6重量份TPA-517作为1,2-醌二叠氮化合物以及0.5重量份RS-932和1.1重量份FZ-2122作为表面活性剂以外,通过进行与比较例1中所述相同的程序获得固体含量为17重量%的组合物。
比较例4:除了使用5.6重量份TPA-517作为1,2-醌二叠氮化合物以及0.5重量份TF-1807和1.1重量份FZ-2122作为表面活性剂以外,通过进行与比较例1中所述相同的程序获得固体含量为17重量%的组合物。
实验实例1:分辨率的评估(感光度)
将实例和比较例中获得的每种组合物通过旋涂涂布在氮化硅基材上,并且将涂布的基材在保持在110℃的热板上预烘烤90秒,以形成干燥的膜。使用发射波长为200nm到450nm的光的对准器(型号名称:MA6)以365nm的波长为基准以0到200mJ/cm2的曝光速率通过具有由2μm到25μm大小范围内的方孔组成的图案的掩模将干燥的膜曝光一定时段,并且通过在23℃下通过喷嘴喷射2.38重量%四甲基氢氧化铵的水性显影剂来显影。然后将曝光的膜在对流烘箱中在230℃下加热30分钟以获得厚度3.0μm的固化膜。
对于通过具有10μm大小的方孔图案的掩模形成的孔图案,测量获得10μm的临界尺寸(CD,线宽,μm)所需的曝光能量的量。曝光能量越低,固化膜的分辨率(感光度)越好。
实验实例2:显影性的评估(在显影时存在浮渣)
将实例和比较例中获得的每种组合物通过旋涂涂布到氮化硅基材上,并且将涂布的基材在保持在110℃的热板上预烘烤90秒,以形成厚度2.1μm的干燥的膜。使用发射波长为200nm到450nm的光的对准器(型号名称:MA6)以365nm的波长为基准以约100mJ/cm2的曝光能量通过图案掩模将干燥的膜曝光一定时间段,并且通过在23℃下通过喷嘴喷射2.38重量%四甲基氢氧化铵的水性显影剂来显影。然后将如此显影的膜在对流烘箱中在230℃下加热30分钟以获得厚度2μm的固化膜。
通过观察在固化膜中形成的图案轮廓来评估显影性。具体而言,通过用扫描电子显微镜观察在固化膜中线宽为10μm的接触孔形成的图案轮廓,按照以下标准评估图案轮廓:
◎:矩形形状清晰,并且没有观察到底部尾部。
○:矩形形状清晰,但表面不光滑。
△:矩形形状清晰,但表面不光滑或留下有斑点的残留膜。
×:矩形形状不清晰,或固化膜未显影。
实验实例3:膜保留率的测量
对于实例和比较例中获得的每种组合物,重复与实验实例2相同的程序,包括预烘烤、通过掩模曝光、显影和热固化,以制备固化膜。通过使用非接触式厚度测量装置(SNUPrecision)计算恰好在预烘烤处理之后的最终固化膜的厚度相对于固化膜的厚度的百分比来获得膜保留率。
实验实例4:透光率的评估
将实例和比较例中获得的每种组合物通过旋涂涂布到玻璃基材上。重复实验实例2中所述的相同程序,包括预烘烤、通过掩模曝光、显影和热固化,以制备厚度约2μm的固化膜。使用紫外线/可见光分光光度计测量400到800nm波长范围内的固化膜的透光率。
实验实例5:氟离子强度的测量
使用实例和比较例中获得的每种组合物经由预烘烤、通过掩模曝光、显影和热固化,根据实验实例2中所述的相同程序获得固化膜。通过SIMS离子分析测量固化膜的氟离子强度。使用SIMS分析仪(TOF SIMS5,由ION TOF Co.,Ltd.制造)测量穿透固化膜的表面至约的厚度的氟含量。在这种情况下,1,000或更大的氟离子强度可被评估为用于赋予防水性的良好程度。
实验实例6:耐化学性的评估
使用实例和比较例中获得的每种组合物经由预烘烤、通过掩模曝光、显影和热固化,根据实验实例2中所述的相同程序获得固化膜。使用ICP(源)经由使用O2/SF6气体(分压比为2.7∶1)的干式蚀刻,将固化膜的表面蚀刻约3,000A持续100秒。使用非接触式厚度测量装置(SNU Precision)测量干式蚀刻后的固化膜的厚度(T1)。将返工化学品(产品名称:LT-360)引入恒温浴中,并且然后将温度保持在50℃。将固化膜浸入浴中5分钟,并且通过空气去除返工化学品。然后,测量固化膜的厚度(T2)。
根据测量值经由以下等式1评估耐化学性(评估耐化学性后,计算溶胀厚度)。在这种情况下,耐化学性评估实验后的溶胀厚度小于可评估其具有良好耐化学性。
[等式1]
耐化学性评估实验后的溶胀厚度(A)=浸入返工化学品后的膜厚度(T2)-浸入返工化学品前的膜厚度(T1)
实验实例7:接触角的测量
根据实验实例6中所述的相同程序,使用实例和比较例中获得的每种组合物获得固化膜,并且执行干式蚀刻处理。使用接触角测量装置进行干式蚀刻后,测量固化膜的表面相对于超纯水的接触角。通常,固化膜的表面在经由干式蚀刻进行蚀刻后可变得不均匀,并且与干式蚀刻之前的表面相比,接触角减小。在干式蚀刻后的接触角增加的情况下,可认为氟组分均匀地分散在固化膜中,并且获得良好的防水性。在干式蚀刻后的接触角为80°或更大的情况下,表面防水性良好,使化学品的溶胀度减到最小,并且耐化学性可被评估为良好。
实验结果总结在下表1中。
[表1]
如表1所示,由本发明的组合物形成的固化膜表现出良好感光度、显影性、保留率、耐化学性和接触角,以及高透光率。相反,根据比较例1到4的不包括在本发明的范围内的组合物由于低氟离子强度而表现出降低的接触角。
Claims (9)
1.一种光敏树脂组合物,包含:
(A)含有氟原子的硅氧烷聚合物;
(B)1,2-醌二叠氮化合物;和
(C)环氧化合物。
2.根据权利要求1所述的光敏树脂组合物,其中所述环氧化合物(C)不包括羧基。
3.根据权利要求1或2所述的光敏树脂组合物,其中所述含有氟原子的硅氧烷聚合物(A)包含至少一种衍生自由下式1表示的硅烷化合物的结构单元:
[式1]
(R1)nSi(OR2)4-n
在式1中,R1为氟原子或含有氟原子的一价烃,其中在R1为所述一价烃的情况下,氢原子可部分或全部被取代,并且在同一分子中存在多个R1的情况下,每个R1可彼此相同或不同;
R2为氢、具有1到6个碳原子的烷基、具有2到6个碳原子的酰基或具有6到15个碳原子的芳基,其中在同一分子中存在多个R2的情况下,每个R2可彼此相同或不同,并且在R2为烷基、酰基或芳基的情况下,氢原子可部分或全部被取代;和
n为1到3的整数。
4.根据权利要求3所述的光敏树脂组合物,其中所述含有氟原子的硅氧烷聚合物(A)还包含至少一种衍生自由下式2表示的硅烷化合物的结构单元:
[式2]
(R3)nSi(OR4)4-n
在式2中,R3为具有1到12个碳原子的烷基、具有2到10个碳原子的烯基或具有6到15个碳原子的芳基,其中在同一分子中存在多个R3的情况下,每个R3可彼此相同或不同,在R3为烷基、烯基或芳基的情况下,氢原子可部分或全部被取代,并且R3可包括含有杂原子的结构单元;
R4为氢、具有1到6个碳原子的烷基、具有2到6个碳原子的酰基或具有6到15个碳原子的芳基,其中在同一分子中存在多个R4的情况下,每个R4可彼此相同或不同,并且在R4为烷基、酰基或芳基的情况下,氢原子可部分或全部被取代;和
n为0到3的整数。
5.根据权利要求4所述的光敏树脂组合物,其中所述含有氟原子的硅氧烷聚合物(A)包含衍生自其中n为0的式2的硅烷化合物的结构单元。
6.根据权利要求1所述的光敏树脂组合物,其中基于Si原子摩尔数,所述含有氟原子的硅氧烷聚合物(A)包含量为在所述硅氧烷聚合物中的所述含氟结构单元的含量(摩尔%)的1到30%的所述氟原子。
7.一种形成图案的方法,包含:
使用根据权利要求1所述的光敏树脂组合物在基材的表面上形成含硅膜;
使用光图案化所述含硅膜;和
干式蚀刻所述图案化的含硅膜和所述基材以在所述基材中形成图案。
8.一种含硅固化膜,通过根据权利要求7所述的方法形成。
9.根据权利要求8所述的含硅固化膜,其中所述含硅固化膜在干式蚀刻后具有80°或更大的接触角。
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PCT/KR2016/010551 WO2017078267A1 (en) | 2015-11-06 | 2016-09-22 | Photosensitive resin composition and cured film prepared therefrom |
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CN113671795A (zh) * | 2021-07-15 | 2021-11-19 | 深圳迪道微电子科技有限公司 | 高残膜率正型光刻胶组合物及其合成方法和固化膜 |
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JP6913679B2 (ja) | 2021-08-04 |
US10890846B2 (en) | 2021-01-12 |
JP2018533761A (ja) | 2018-11-15 |
KR20170053442A (ko) | 2017-05-16 |
CN108139671B (zh) | 2022-02-11 |
US20180314153A1 (en) | 2018-11-01 |
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