CN113892058A - 感光性树脂组合物和其固化膜 - Google Patents
感光性树脂组合物和其固化膜 Download PDFInfo
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- CN113892058A CN113892058A CN202080039858.2A CN202080039858A CN113892058A CN 113892058 A CN113892058 A CN 113892058A CN 202080039858 A CN202080039858 A CN 202080039858A CN 113892058 A CN113892058 A CN 113892058A
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- resin composition
- photosensitive resin
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- polyimide
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- 239000011342 resin composition Substances 0.000 title claims abstract description 61
- 229920001721 polyimide Polymers 0.000 claims abstract description 102
- 239000009719 polyimide resin Substances 0.000 claims abstract description 63
- 239000002904 solvent Substances 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 29
- 230000015572 biosynthetic process Effects 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000004122 cyclic group Chemical group 0.000 claims description 10
- 239000003999 initiator Substances 0.000 claims description 9
- 125000002723 alicyclic group Chemical group 0.000 claims description 7
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 7
- CGSKOGYKWHUSLC-UHFFFAOYSA-N 1-(4-aminophenyl)-1,3,3-trimethyl-2h-inden-5-amine Chemical compound C12=CC=C(N)C=C2C(C)(C)CC1(C)C1=CC=C(N)C=C1 CGSKOGYKWHUSLC-UHFFFAOYSA-N 0.000 claims description 6
- KWOIWTRRPFHBSI-UHFFFAOYSA-N 4-[2-[3-[2-(4-aminophenyl)propan-2-yl]phenyl]propan-2-yl]aniline Chemical compound C=1C=CC(C(C)(C)C=2C=CC(N)=CC=2)=CC=1C(C)(C)C1=CC=C(N)C=C1 KWOIWTRRPFHBSI-UHFFFAOYSA-N 0.000 claims description 6
- 125000002015 acyclic group Chemical group 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- VIUDTWATMPPKEL-UHFFFAOYSA-N 3-(trifluoromethyl)aniline Chemical compound NC1=CC=CC(C(F)(F)F)=C1 VIUDTWATMPPKEL-UHFFFAOYSA-N 0.000 claims description 5
- 239000000178 monomer Substances 0.000 claims description 5
- 238000002834 transmittance Methods 0.000 claims description 5
- NVKGJHAQGWCWDI-UHFFFAOYSA-N 4-[4-amino-2-(trifluoromethyl)phenyl]-3-(trifluoromethyl)aniline Chemical group FC(F)(F)C1=CC(N)=CC=C1C1=CC=C(N)C=C1C(F)(F)F NVKGJHAQGWCWDI-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 229910052727 yttrium Inorganic materials 0.000 claims description 4
- 125000005375 organosiloxane group Chemical group 0.000 claims description 2
- 239000010408 film Substances 0.000 description 64
- 239000004642 Polyimide Substances 0.000 description 39
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 26
- 238000003786 synthesis reaction Methods 0.000 description 25
- 150000004985 diamines Chemical group 0.000 description 23
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 20
- 238000000034 method Methods 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
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- 239000002966 varnish Substances 0.000 description 17
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 14
- 238000011161 development Methods 0.000 description 14
- -1 acryl Chemical group 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
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- 239000010703 silicon Substances 0.000 description 10
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- 235000012431 wafers Nutrition 0.000 description 10
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 9
- 125000000524 functional group Chemical group 0.000 description 9
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- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 8
- 125000003277 amino group Chemical group 0.000 description 8
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- MHRLWUPLSHYLOK-UHFFFAOYSA-N thiomorpholine-3,5-dicarboxylic acid Chemical compound OC(=O)C1CSCC(C(O)=O)N1 MHRLWUPLSHYLOK-UHFFFAOYSA-N 0.000 description 8
- 238000001723 curing Methods 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- RZIPTXDCNDIINL-UHFFFAOYSA-N cyclohexane-1,1,2,2-tetracarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCCCC1(C(O)=O)C(O)=O RZIPTXDCNDIINL-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 150000004984 aromatic diamines Chemical class 0.000 description 5
- 125000003700 epoxy group Chemical group 0.000 description 5
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- LJMPOXUWPWEILS-UHFFFAOYSA-N 3a,4,4a,7a,8,8a-hexahydrofuro[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1C2C(=O)OC(=O)C2CC2C(=O)OC(=O)C21 LJMPOXUWPWEILS-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 4
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 4
- 230000001681 protective effect Effects 0.000 description 4
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 3
- YLHUPYSUKYAIBW-UHFFFAOYSA-N 1-acetylpyrrolidin-2-one Chemical compound CC(=O)N1CCCC1=O YLHUPYSUKYAIBW-UHFFFAOYSA-N 0.000 description 3
- LVUQCTGSDJLWCE-UHFFFAOYSA-N 1-benzylpyrrolidin-2-one Chemical compound O=C1CCCN1CC1=CC=CC=C1 LVUQCTGSDJLWCE-UHFFFAOYSA-N 0.000 description 3
- DPNXHTDWGGVXID-UHFFFAOYSA-N 2-isocyanatoethyl prop-2-enoate Chemical compound C=CC(=O)OCCN=C=O DPNXHTDWGGVXID-UHFFFAOYSA-N 0.000 description 3
- YGYCECQIOXZODZ-UHFFFAOYSA-N 4415-87-6 Chemical compound O=C1OC(=O)C2C1C1C(=O)OC(=O)C12 YGYCECQIOXZODZ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- QISSLHPKTCLLDL-UHFFFAOYSA-N N-Acetylcaprolactam Chemical compound CC(=O)N1CCCCCC1=O QISSLHPKTCLLDL-UHFFFAOYSA-N 0.000 description 3
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- CURBACXRQKTCKZ-UHFFFAOYSA-N cyclobutane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1C(C(O)=O)C(C(O)=O)C1C(O)=O CURBACXRQKTCKZ-UHFFFAOYSA-N 0.000 description 3
- STZIXLPVKZUAMV-UHFFFAOYSA-N cyclopentane-1,1,2,2-tetracarboxylic acid Chemical class OC(=O)C1(C(O)=O)CCCC1(C(O)=O)C(O)=O STZIXLPVKZUAMV-UHFFFAOYSA-N 0.000 description 3
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- QEGNUYASOUJEHD-UHFFFAOYSA-N 1,1-dimethylcyclohexane Chemical compound CC1(C)CCCCC1 QEGNUYASOUJEHD-UHFFFAOYSA-N 0.000 description 2
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 2
- KRPRVQWGKLEFKN-UHFFFAOYSA-N 3-(3-aminopropoxy)propan-1-amine Chemical compound NCCCOCCCN KRPRVQWGKLEFKN-UHFFFAOYSA-N 0.000 description 2
- ORTCGSWQDZPULK-UHFFFAOYSA-N 3-isocyanatopropyl prop-2-enoate Chemical compound C=CC(=O)OCCCN=C=O ORTCGSWQDZPULK-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- ZPAKUZKMGJJMAA-UHFFFAOYSA-N Cyclohexane-1,2,4,5-tetracarboxylic acid Chemical compound OC(=O)C1CC(C(O)=O)C(C(O)=O)CC1C(O)=O ZPAKUZKMGJJMAA-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
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- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
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- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 2
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 2
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- 238000007611 bar coating method Methods 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 2
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- 125000005843 halogen group Chemical group 0.000 description 2
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- 238000000691 measurement method Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
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- 229910052757 nitrogen Inorganic materials 0.000 description 2
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Abstract
提供一种感光性树脂组合物,其中,聚酰亚胺树脂(A)具有特定的结构、且重均分子量为70000以下。
Description
技术领域
本发明涉及感光性树脂组合物和其固化膜。
背景技术
电子设备的半导体元件的表面保护膜、层间绝缘膜、电路基板的布线保护绝缘膜等中广泛使用有耐热性、绝缘性优异的聚酰亚胺系树脂。对于半导体集成电路等的绝缘材料,从近年来的高密度化、高集成化的观点出发,要求优于以往的图案显影性,且还要求高绝缘性、耐热性的改善、低温固化性、耐裂纹性、柔软性之类的各种物性。曝光部与未曝光部的溶解性的差越大,显影性越良好,为了改善显影性,重要的是,扩大曝光部与未曝光部的溶解性之差。另外,为了体现期望的物性,还需要适当选择基础聚合物的原料,进行聚合物设计。
聚酰亚胺的溶剂溶解性低,因此,作为用于得到感光性聚酰亚胺的手法,提出了在聚酰亚胺前体中导入聚合性基团的方法。专利文献1中提出了在聚酰亚胺前体的侧链中导入聚合性基团的方法。专利文献2中提出了在聚酰亚胺前体的末端导入聚合性基团的方法。
另一方面,提出了在溶剂可溶性的聚酰亚胺中导入聚合性基团的方法。为了能以高密度导入聚合性基团,提出了在侧链具有聚合性基团的聚酰亚胺。专利文献3中提出了在聚酰亚胺的侧链设置聚合性基团的方法。
现有技术文献
专利文献
专利文献1:日本特开2013-76845号公报
专利文献2:国际公开第2018/003725号
专利文献3:日本特开2000-147761号公报
发明内容
发明要解决的问题
专利文献1和2公开的方法中,为了得到聚酰亚胺,需要将聚酰亚胺前体在高温下长时间加热,不适于要求低温固化的领域。另外,如果还包括由聚酰亚胺前体得到聚酰亚胺的加热工序,则引起约50%的体积收缩,因此,存在成为翘曲、裂纹的原因的课题。
专利文献3公开的方法中,需要导入官能团以在聚酰亚胺的侧链设置聚合性基团,因此,聚酰亚胺合成的原料选择项受限。另外,在侧链设置聚合性基团的方法能以高密度导入聚合性基团,因此,固化性良好,但另一方面,存在固化收缩率大、容易产生裂纹的课题。
本发明鉴于上述情况,目的在于,提供:无需加热工序、显影性优异、聚酰亚胺原料选择具有自由度、固化收缩性低的、感光性树脂组合物。
用于解决问题的方案
本发明人等进行了深入研究,结果发现:包含具有特定结构和特定末端结构、且具有特定的重均分子量的聚酰亚胺树脂的感光性树脂组合物解决了上述课题。
本发明涉及以下的感光性树脂组合物和其固化膜。
[1]一种感光性树脂组合物,其包含聚酰亚胺树脂(A),所述聚酰亚胺树脂(A)具有下述通式(1)所示的结构、且重均分子量为70000以下。
[通式(1)中,R为具有环状结构、具有非环状结构、或具有环状结构和非环状结构的碳数4~10的4价的基团。A具有选自由脂肪族烃基、脂环式烃基、芳香族烃基、和有机硅氧烷基组成的组中的至少1种基团、且为碳数2~39的2价的基团。在A的主链上任选插入有选自由-O-、-SO2-、-CO-、-CH2-、-C(CH3)2-、-C2H4O-、和-S-组成的组中的至少1种基团。n表示重复单元数。通式(1)的末端为下述式(2)或式(3)所示的基团、或氢原子中的任意者,且末端的至少一者为式(2)或式(3)所示的基团。]
[通式(2)和(3)中,X和X2各自独立地为碳数2~15的基团,X和X2任选具有选自由酯键和双键组成的组中的至少1个基团。Y和Y2各自独立地为氢原子或甲基。]
[2]根据上述[1]所述的感光性树脂组合物,其中,前述聚酰亚胺树脂(A)的重均分子量为5000以上。
[3]根据上述[1]或[2]所述的感光性树脂组合物,其中,前述聚酰亚胺树脂(A)在波长200~400nm下的透光率为50%以上。
[4]根据上述[1]~[3]中任一项所述的感光性树脂组合物,其中,在波长365nm下的曝光量1500~2500mJ/cm2的条件下曝光后的未曝光部的残膜率为40%以下。
[5]根据上述[1]~[4]中任一项所述的感光性树脂组合物,其中,前述通式(1)中的A包含芳香环作为芳香族烃基。
[6]根据上述[1]~[5]中任一项所述的感光性树脂组合物,其中,前述通式(1)的A包含选自由以下所示的结构组成的组中的至少1种以上。
[式中,*表示原子键。]
[7]根据上述[1]~[6]中任一项所述的感光性树脂组合物,其中,前述聚酰亚胺树脂(A)包含由4,4’-二氨基-2,2’-双(三氟甲基)联苯、1-(4-氨基苯基)-2,3-二氢-1,3,3-三甲基-1H-茚-5-胺、4,4’-氧双[3-(三氟甲基)苯胺]、或1,3-双[2-(4-氨基苯基)-2-丙基]苯构成的单元中的至少1种。
[8]根据上述[1]~[7]中任一项所述的感光性树脂组合物,其中,还包含选自由光聚合引发剂、溶剂、和光聚合性化合物组成的组中的至少1种。
[9]根据上述[8]所述的感光性树脂组合物,其中,前述光聚合性化合物为多官能自由基聚合性单体。
[10]根据上述[1]~[9]中任一项所述的感光性树脂组合物,其中,还包含敏化剂。
[11]根据上述[1]~[10]中任一项所述的感光性树脂组合物,其用于绝缘膜的形成。
[12]一种固化膜,其是使上述[1]~[11]中任一项所述的感光性树脂组合物固化而成的。
[13]根据上述[12]所述的固化膜,其膜厚为10~85μm。
发明的效果
根据本发明,可以得到:无需加热工序、由于透明性高、溶剂溶解性优异因而显影性优异、聚酰亚胺原料选择具有自由度的、感光性树脂组合物。该树脂组合物的固化收缩性低,因此,可以有效地抑制得到的固化膜的裂纹等的发生。
具体实施方式
对用于实施本发明的方式(以下,简称为“本实施方式”)详细地进行说明。以下的本实施方式为用于说明本发明的示例,不限定本发明的内容。本发明在其主旨的范围内可以适宜变形而实施。本说明书中,可以任意采用所谓优选的限定,可以说更优选的是优选者的彼此的组合。本说明书中,“XX~YY”的记载是指,“XX以上且YY以下”。
本说明书中的“(甲基)丙烯酸酯”是指,“丙烯酸酯”和“甲基丙烯酸酯”这两者。对于其他类似术语(“(甲基)丙烯酸”、“(甲基)丙烯酰基”等)也同样。
[聚酰亚胺树脂(A)]
本实施方式的聚酰亚胺树脂(A)具有下述通式(1)所示的结构、且重均分子量为70000以下。
[通式(1)中,R为具有环状结构、具有非环状结构、或具有环状结构和非环状结构的碳数4~10的4价的基团。A具有选自由脂肪族烃基、脂环式烃基、芳香族烃基、和有机硅氧烷基组成的组中的至少1种基团、且为碳数2~39的2价的基团。在A的主链上任选插入选自由-O-、-SO2-、-CO-、-CH2-、-C(CH3)2-、-C2H4O-、和-S-组成的组中的至少1种基团。n表示重复单元数。通式(1)的末端为下述式(2)或式(3)所示的基团、或氢原子中的任意者,且末端的至少一者为式(2)或式(3)所示的基团。]
[通式(2)和(3)中,X和X2各自独立地为碳数2~15的基团,X和X2任选具有选自由酯键和双键组成的组中的至少1个基团。Y和Y2各自独立地为氢原子或甲基。]
上述式(1)中的R优选至少具有环状结构,作为该环状结构,例如可以举出:从环己烷、环戊烷、环丁烷、双环戊烷和它们的立体异构体中去除4个氢原子而形成的4价的基团。作为该4价的基团,更具体而言,可以举出下述结构式所示的基团。
[式中,*表示原子键。]
上述中,更优选从环己烷中去除4个氢原子而形成的4价的基团。
式(1)中的A为具有选自由脂肪族烃基、脂环式烃基、芳香族烃基、和有机硅氧烷基组成的组中的至少1种基团的、碳数2~39的2价的基团。在A的主链上任选插入有选自由-O-、-SO2-、-CO-、-CH2-、-C(CH3)2-、-C2H4O-、和-S-组成的组中的至少1种基团。
A更具体而言可以举出:从环己烷、二环己基甲烷、二甲基环己烷、异佛尔酮、降冰片烷和它们的烷基取代体、以及卤素取代体;苯、萘、联苯、二苯基甲烷、二苯醚、二苯基砜、二苯甲酮和它们的烷基取代体以及卤素取代体;有机(聚)硅氧烷等化合物中去除2个氢原子而形成的2价的基团。A优选具有环状结构,优选具有脂环式烃基和/或芳香环。A优选具有芳香环作为芳香族烃基。更具体而言,优选举出下述结构式所示的碳数6~27的2价的基团。
[式中,*表示原子键。]
作为与上述示例的A相当的基团,更优选包含选自由以下所示的结构组成的组中的至少1种以上。
[式中,*表示原子键。]
表示式(1)所示的结构单元的重复单元数的n优选5~250、更优选10~200、进一步优选15~150。n如果为15以上,则可以形成具有期望的机械物性的固化膜。n如果为250以下,则可以确保充分的溶剂溶解性。
本实施方式的聚酰亚胺树脂(A)在末端具有上述通式(2)或通式(3)所示的基团、或氢原子中的任意者,末端的至少一者为通式(2)或通式(3)所示的基团。聚酰亚胺树脂(A)的一个末端可以具有通式(2)或通式(3)所示的结构,或两末端可以具有通式(2)或通式(3)所示的结构。
通式(2)或通式(3)中的X或X2所示的基团为碳数2~15的基团,任选具有选自由酯键和双键组成的组中的至少1个基团。Y或Y2所示的基团为氢原子或甲基。
上述通式(2)或通式(3)所示的结构更具体而言相当于使聚酰亚胺树脂(A)的末端二胺与含官能团化合物反应而得到的结构。作为上述含官能团化合物,可以举出:具有异氰酸酯基或环氧基、且具有(甲基)丙烯酰基的化合物。作为该化合物,可以举出甲基丙烯酸2-异氰酸根合乙酯、丙烯酸2-异氰酸根合乙酯、1,1-双(丙烯酰氧基甲基)乙基异氰酸酯、甲基丙烯酸缩水甘油酯、丙烯酸缩水甘油酯、烯丙基缩水甘油醚等。通式(2)或通式(3)所示的结构可以具有该化合物与胺末端反应而成的结构。
聚酰亚胺树脂(A)的重均分子量必须为70000以下。重均分子量如果超过70000,则树脂组合物的溶剂溶解性降低,因此,不适于形成固化膜。重均分子量优选60000以下,更优选50000以下,进一步优选45000以下,更进一步优选40000以下,更进一步优选35000以下,更进一步优选30000以下,特别优选低于30000。为了可以得到具有期望的机械物性的固化膜,聚酰亚胺树脂(A)的重均分子量优选5000以上。聚酰亚胺树脂(A)的重均分子量更优选10000以上、进一步优选13000以上、更进一步优选15000以上。聚酰亚胺树脂(A)的重均分子量通过处于上述范围,从而未曝光部的残膜率低,可以得到具有优异的显影性的树脂组合物。
聚酰亚胺树脂(A)可以通过使以下详述的二胺成分与四羧酸成分反应而得到。
<二胺成分>
作为二胺成分,可以举出二胺、二异氰酸酯和二氨基二硅烷类等,优选二胺。用作原料的二胺成分中的二胺含量优选50摩尔%以上、可以为100摩尔%。
上述二胺可以为脂肪族二胺和芳香族二胺中的任意者,也可以为它们的混合物。本发明中“芳香族二胺”是指,氨基直接键合于芳香族环的二胺,在其结构的一部分中任选包含脂肪族基团、脂环基、其他取代基。“脂肪族二胺”是指,氨基直接键合于脂肪族基团或脂环基的二胺,其结构的一部分中任选包含芳香族基团、其他取代基。
通常,使用脂肪族二胺作为聚酰亚胺树脂的原料时,作为中间产物的聚酰胺酸与脂肪族二胺形成牢固的络合物,因此,不易得到高分子量聚酰亚胺。因此,需要使用例如甲酚等络合物的溶解性较高的溶剂等的工夫。使用环己烷四羧酸、环丁烷四羧酸或它们的衍生物作为四羧酸成分时,形成聚酰胺酸与脂肪族二胺的结合较弱的络合物,因此,可以容易使聚酰亚胺高分子量化。作为二胺,选择具有氟取代基的二胺作为原料时,得到的聚酰亚胺树脂的透明性优异,故优选。
作为上述脂肪族二胺,可以使用任意的物质。作为脂肪族二胺,例如可以举出:4,4’-二氨基二环己基甲烷、乙二胺、六亚甲基二胺、聚乙二醇双(3-氨基丙基)醚、聚丙二醇双(3-氨基丙基)醚、1,3-双(氨基甲基)环己烷、1,4-双(氨基甲基)环己烷、间苯二甲胺、对苯二甲胺、异佛尔酮二胺、降冰片烷二胺和硅氧烷二胺类等。
作为上述芳香族二胺,例如可以举出:4,4’-二氨基二苯醚、4,4’-二氨基二苯基甲烷、4,4’-二氨基二苯基砜、间苯二胺、对苯二胺、二氨基二苯甲酮、2,6-二氨基萘、1,5-二氨基萘、4,4’-二氨基-2,2’-双(三氟甲基)联苯、4,4’-氧双[3-(三氟甲基)苯胺]、1-(4-氨基苯基)-2,3-二氢-1,3,3-三甲基-1H-茚-5-胺和1,3-双[2-(4-氨基苯基)-2-丙基]苯等。
上述二胺优选至少包含4,4’-二氨基-2,2’-双(三氟甲基)联苯、4,4’-氧双[3-(三氟甲基)苯胺]、1-(4-氨基苯基)-2,3-二氢-1,3,3-三甲基-1H-茚-5-胺或1,3-双[2-(4-氨基苯基)-2-丙基]苯。通过至少包含任意者作为二胺成分,从而包含得到的聚酰亚胺树脂(A)的感光性树脂组合物具有特定波长下的高的透光率和高的溶剂溶解性。因此,曝光部的固化性优异,且未曝光部的残膜率低,具有优异的显影性。只要包含上述任意者作为二胺成分即可,即使与其他二胺组合而使用,也可以维持优异的效果。本实施方式的聚酰亚胺树脂(A)优选包含由上述4,4’-二氨基-2,2’-双(三氟甲基)联苯、1-(4-氨基苯基)-2,3-二氢-1,3,3-三甲基-1H-茚-5-胺、4,4’-氧双[3-(三氟甲基)苯胺]或1,3-双[2-(4-氨基苯基)-2-丙基]苯构成的单元中的至少1种。
<四羧酸成分>
作为四羧酸成分,可以使用任意物质。作为四羧酸成分,例如可以举出环己烷四羧酸、环己烷四羧酸酯类、环己烷四羧酸二酐、环丁烷四羧酸、环丁烷四羧酸酯类、环丁烷四羧酸二酐、环戊烷四羧酸、环戊烷四羧酸酯类、环戊烷四羧酸二酐、双环戊烷四羧酸二酐等。其中,更优选可以举出环己烷四羧酸二酐、环丁烷四羧酸二酐和环戊烷四羧酸二酐。上述中,进一步优选环己烷四羧酸二酐。上述各种四羧酸成分包含位置异构体。
作为上述四羧酸成分的更优选的具体例,可以举出1,2,4,5-环己烷四羧酸、1,2,4,5-环己烷四羧酸二酐、1,2,4,5-环己烷四羧酸甲酯、1,2,3,4-丁烷四羧酸、1,2,3,4-丁烷四羧酸二酐、1,2,3,4-丁烷四羧酸甲酯、1,2,3,4-环丁烷四羧酸、1,2,3,4-环丁烷四羧酸二酐、1,2,3,4-环丁烷四羧酸甲酯、1,2,4,5-环戊烷四羧酸、1,2,4,5-环戊烷四羧酸二酐、1,2,4,5-环戊烷四羧酸甲酯、3-羧基甲基-1,2,4-环戊烷三羧酸、双环[2.2.2]辛-7-烯-2,3,5,6-四羧酸、双环[2.2.2]辛-7-烯-2,3,5,6-四羧酸二酐、双环[2.2.2]辛-7-烯-2,3,5,6-四羧酸甲酯、二环己基四羧酸、二环己基四羧酸二酐和二环己基四羧酸甲酯等。
其中,1,2,4,5-环己烷四羧酸、1,2,4,5-环己烷四羧酸二酐、1,2,3,4-环丁烷四羧酸二酐、1,2,4,5-环己烷四羧酸甲酯在制造聚酰亚胺树脂时高分子量化容易、容易得到柔性的薄膜的方面是有利的,故特别优选。
四羧酸成分在不有损最终得到的固化膜、例如薄膜的挠性、热压接性的范围内,可以包含其他四羧酸或其衍生物。作为这些其他四羧酸或其衍生物,例如可以举出选自均苯四酸、3,3’,4,4’-联苯四羧酸、2,3,3’,4’-联苯四羧酸、2,2-双(3,4-二羧基苯基)丙烷、2,2-双(2,3-二羧基苯基)丙烷、2,2-双(3,4-二羧基苯基)-1,1,1,3,3,3-六氟丙烷、2,2-双(2,3-二羧基苯基)-1,1,1,3,3,3-六氟丙烷、双(3,4-二羧基苯基)砜、双(3,4-二羧基苯基)醚、双(2,3-二羧基苯基)醚、3,3’,4,4’-二苯甲酮四羧酸、2,2’,3,3’-二苯甲酮四羧酸、4,4-(对亚苯基二氧基)二苯二甲酸、4,4-(间亚苯基二氧基)二苯二甲酸、亚乙基四羧酸、1,1-双(2,3-二羧基苯基)乙烷、双(2,3-二羧基苯基)甲烷、双(3,4-二羧基苯基)甲烷和它们的衍生物中的至少1种。
<聚酰亚胺树脂的制备方法>
本实施方式的感光性树脂组合物中所含的聚酰亚胺树脂(A)可以通过以下的工序(1)和(2)而得到:
工序(1):使四羧酸成分与二胺成分反应,得到在末端具有氨基的聚酰亚胺树脂。
工序(2):使上述工序(1)中得到的在末端具有氨基的聚酰亚胺树脂、与上述含官能团化合物(具有异氰酸酯基或环氧基、且具有(甲基)丙烯酰基的化合物)反应。
<工序(1)>
使上述四羧酸与二胺成分反应,得到在末端具有氨基的聚酰亚胺树脂。
使四羧酸成分与二胺成分反应时使用的有机溶剂没有特别限定,例如优选包含选自由环状醚、环状酮、环状酯、酰胺和脲组成的组中的至少1种的有机溶剂。作为适合的溶剂的具体例,没有特别限定,可以举出选自由γ-丁内酯、N,N-二甲基乙酰胺、N,N-二甲基甲酰胺、N-甲基-2-吡咯烷酮、二甲基亚砜、六甲基磷酰胺、环戊酮、环己酮、1,3-二氧戊环、1,4-二氧杂环己烷、四甲基脲和四氢呋喃等非质子性的极性有机溶剂组成的组中的至少1种。其中,更优选选自由γ-丁内酯、N,N-二甲基乙酰胺、N,N-二甲基甲酰胺和N-甲基-2-吡咯烷酮组成的组中的1种以上。
工序(1)中使四羧酸成分与二胺成分反应时,可以使用酰亚胺化催化剂。作为酰亚胺化催化剂,优选叔胺化合物,具体地,可以使用选自由三甲胺、三乙胺(TEA)、三丙胺、三丁胺、三乙醇胺、N,N-二甲基乙醇胺、N,N-二乙基乙醇胺、三乙二胺、N-甲基吡咯烷、N-乙基吡咯烷、N-甲基哌啶、N-乙基哌啶、咪唑、吡啶、喹啉和异喹啉组成的组中的至少1种。
工序(1)中的反应温度通常为160~200℃的范围、优选170~190℃的范围、更优选180~190℃的范围。如果为160℃以上,则酰亚胺化和高分子量化充分进行。如果为200℃以下,则可以适当保持溶液粘度,可以避免树脂在反应容器的壁面烧焦等不良情况。根据情况,可以使用甲苯、二甲苯等共沸脱水剂。反应压力通常为常压,根据需要也可以在加压下进行反应。作为反应温度的保持时间,优选至少1小时以上、更优选3小时以上。如果为1小时以上,则可以充分进行酰亚胺化和高分子量化。对于反应时间,上限无特别,通常在3~10小时的范围内进行。
工序(1)中,理想的是,使四羧酸成分“A摩尔”与二胺成分“B摩尔”优选在0.80≤A/B≤0.99的范围内反应,更优选在0.85≤A/B≤0.95的范围内反应。通过设为A/B≤0.99,从而可以使聚酰亚胺的末端为二胺过剩,可以得到在末端具有氨基的聚酰亚胺树脂,且可以得到具有充分的溶剂溶解性的分子量的聚酰亚胺树脂。如果为0.80≤A/B,则可以得到体现充分的柔软性的分子量的聚酰亚胺树脂。
A/B越接近于1.0,可以得到分子量越高的聚酰亚胺树脂,因此,通过适宜调整A/B,从而可以得到目标分子量的聚酰亚胺树脂。
<工序(2)>
工序(2)为将上述工序(1)中得到的聚酰亚胺树脂的末端进行改性的工序。具体而言,如上述,使聚酰亚胺与上述含官能团化合物(具有异氰酸酯基或环氧基、且具有(甲基)丙烯酰基的化合物)反应,得到在末端具有(甲基)丙烯酰基的聚酰亚胺树脂。
使聚酰亚胺树脂的末端改性的、含官能团化合物为具有异氰酸酯基或环氧基、且具有(甲基)丙烯酰基的化合物,具体而言,可以举出甲基丙烯酸2-异氰酸根合乙酯、丙烯酸2-异氰酸根合乙酯、1,1-双(丙烯酰氧基甲基)乙基异氰酸酯、甲基丙烯酸缩水甘油酯、和烯丙基缩水甘油醚等。这些含官能团化合物可以单独使用,也可以组合2种以上而使用。含官能团化合物优选以相对于包含在末端具有(甲基)丙烯酰基的聚酰亚胺树脂的溶液中的固体成分为0.1~30摩尔倍的比例使用。
工序(2)中的反应温度优选30~100℃的范围,反应时间优选1~5小时。
使聚酰亚胺树脂的氨基末端、与含官能团化合物的异氰酸酯基或环氧基反应时,可以直接进行反应,也可以根据需要在催化剂的存在下进行反应。作为该催化剂,可以举出三乙胺等胺化合物、三苯基膦等有机磷系化合物等,它们可以单独使用,也可以组合2种以上而使用。为了抑制反应时的副反应,也可以使用阻聚剂。作为阻聚剂,可以举出氢醌、氢醌单甲醚、和甲基氢醌等,它们可以单独使用,也可以组合2种以上而使用。
本实施方式的感光性树脂组合物中所含的聚酰亚胺树脂(A)的波长200~400nm的透光率优选50%以上、更优选55%以上、进一步优选60%以上、进一步更优选70%以上。
本实施方式的感光性树脂组合物中所含的聚酰亚胺树脂(A)在上述波长下具有高的透光率,且具有优异的溶剂溶解性。因此,可以包含在该组合物中的光聚合引发剂有效地作用,因此,可以效率良好地得到固化膜。此外,通过使用具有特定结构和特定末端结构、且具有特定的分子量的聚酰亚胺树脂(A),从而由后述的组合物形成固化膜时,未曝光部的残膜率低,具有优异的显影性,且可以有效地抑制裂纹等的发生。
[感光性聚酰亚胺树脂组合物]
本实施方式中的感光性聚酰亚胺树脂组合物包含具有上述通式(1)的结构和通式(2)所示的末端结构的聚酰亚胺树脂(A)。除该聚酰亚胺树脂(A)之外,优选还包含例如选自由光聚合引发剂、溶剂、和光聚合性化合物组成的组中的至少1种。也优选还包含敏化剂。
作为溶剂,可以举出N-甲基-2-吡咯烷酮、N-乙酰基-2-吡咯烷酮、N-苄基-2-吡咯烷酮、N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、二甲基亚砜、六甲基磷三酰胺、N-乙酰基-ε-己内酰胺、二甲基咪唑烷酮、二乙二醇二甲醚、三乙二醇二甲醚和γ-丁内酯等。这些溶剂可以单独使用,也可以组合2种以上而使用。
通过使用适当的溶剂,从而可以以溶液(清漆)状态使用本实施方式的感光性树脂组合物,成膜时是便利的。
作为光聚合性化合物,可以使用多官能自由基聚合性单体、例如2官能以上的(甲基)丙烯酸类单体。
作为(甲基)丙烯酸类单体,例如可以举出三环癸烷二甲醇二丙烯酸酯、三环癸烷二甲醇二甲基丙烯酸酯、聚丙二醇二丙烯酸酯、三羟甲基丙烷三丙烯酸酯、三羟甲基丙烷三甲基丙烯酸酯、季戊四醇四丙烯酸酯、季戊四醇三丙烯酸酯、三-(2-丙烯酰氧基乙基)异氰脲酸酯、二(三羟甲基)丙烷四丙烯酸酯、二季戊四醇六丙烯酸酯等。这些光聚合性化合物可以单独使用,也可以组合2种以上而使用。
根据混合的光聚合性化合物的结构可以控制聚酰亚胺树脂组合物的柔软性、耐热性。这些光聚合性化合物优选以相对于包含在末端具有(甲基)丙烯酰基的聚酰亚胺树脂的溶液中的固体成分为5~500质量份的比例混合。
光聚合引发剂没有特别限定,可以使用公知的物质。例如可以举出:2,2-二甲氧基-1,2-二苯基乙烷-1-酮、1-羟基环己基苯基酮、2-羟基-2-甲基-1-苯基-丙烷-1-酮、1-[4-(2-羟基乙氧基)-苯基]-2-羟基-2-甲基-1-丙烷-1-酮、2-羟基-1-{4-[4-(2-羟基-2-甲基-丙酰基)-苄基]苯基}-2-甲基-丙烷-1-酮、2-甲基-1-(4-甲基硫代苯基)-2-吗啉代丙烷-1-酮、2-苄基-2-二甲基氨基-1-(4-吗啉代苯基)-丁酮-1、2-(二甲基氨基)-2-[(4-甲基苯基)甲基]-1-[4-(4-吗啉基)苯基]-1-丁酮、2,4,6-三甲基苯甲酰基-二苯基氧化膦和双(2,4,6-三甲基苯甲酰基)苯基氧化膦等。
这些光聚合引发剂可以单独使用,也可以组合2种以上而使用。
光聚合引发剂优选以相对于包含在末端具有(甲基)丙烯酰基的聚酰亚胺树脂的溶液中的固体成分为0.1~10质量份的比例混合。
敏化剂没有特别限定,可以使用公知的物质。例如可以举出含氨基敏化剂,可以优选示例在同一分子内具有氨基和苯基的化合物。更具体而言,可以举出4,4’-二甲基氨基二苯甲酮、4,4’-二乙基氨基二苯甲酮、2-氨基二苯甲酮、4-氨基二苯甲酮、4,4’-二氨基二苯甲酮、3,3’-二氨基二苯甲酮、3,4-二氨基二苯甲酮等二苯甲酮系化合物;2-(对二甲基氨基苯基)苯并噁唑、2-(对二乙基氨基苯基)苯并噁唑、2-(对二甲基氨基苯基)苯并[4,5]苯并噁唑、2-(对二甲基氨基苯基)苯并[6,7]苯并噁唑、2,5-双(对二乙基氨基苯基)-1,3,4-噁二唑、2-(对二甲基氨基苯基)苯并噻唑、2-(对二乙基氨基苯基)苯并噻唑、2-(对二甲基氨基苯基)苯并咪唑、2-(对二乙基氨基苯基)苯并咪唑、2,5-双(对二乙基氨基苯基)-1,3,4-噻二唑、(对二甲基氨基苯基)吡啶、(对二乙基氨基苯基)吡啶、(对二甲基氨基苯基)喹啉、(对二乙基氨基苯基)喹啉、(对二甲基氨基苯基)嘧啶、(对二乙基氨基苯基)嘧啶等含对二烷基氨基苯基化合物等。
这些敏化剂可以单独使用,也可以组合2种以上而使用。
敏化剂优选以相对于包含在末端具有(甲基)丙烯酰基的聚酰亚胺树脂的溶液中的固体成分为0.001~10质量份的比例混合。
本实施方式的感光性树脂组合物没有特别限定,可以如以下制备。
在具有通式(1)所示的结构、且具有通式(2)或(3)所示的末端结构的聚酰亚胺树脂(A)中根据需要混合选自由溶剂、光聚合引发剂、光聚合性化合物和敏化剂组成的组中的至少1种,得到感光性聚酰亚胺组合物。
本实施方式的感光性树脂组合物可以特别适合用于绝缘膜的形成。
[固化膜]
得到本实施方式中的固化膜的情况下,将包含具有上述结构特征的聚酰亚胺树脂(A)的溶液涂布在基材上。
在基材上涂布的方法没有特别限定,具体而言,可以举出喷墨法、旋涂法、浇铸法、微凹版法、凹版涂布法、棒涂法、辊涂法、线棒涂法、浸涂法、喷涂法、丝网印刷法、柔性印刷法、模涂法等。
涂布在基材上时,优选调整包含本实施方式的聚酰亚胺树脂(A)的溶液的固体成分浓度使其成为5~50质量%的范围。作为涂布时使用的溶剂,从溶解性的观点出发,期望非质子性极性溶剂。具体而言,可以举出N-甲基-2-吡咯烷酮、N-乙酰基-2-吡咯烷酮、N-苄基-2-吡咯烷酮、N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、二甲基亚砜、六甲基磷三酰胺、N-乙酰基-ε-己内酰胺、二甲基咪唑烷酮、二乙二醇二甲醚、三乙二醇二甲醚、γ-丁内酯等作为适合例。这些溶剂可以单独使用,也可以组合2种以上而使用。为了进一步改善涂布性,可以在不对聚合物的溶解性造成不良影响的范围内混合甲苯、二甲苯、二乙基酮、甲氧基苯、环戊酮等溶剂。
作为上述基材,可以举出玻璃、硅晶圆、金属箔、塑料薄膜。上述金属箔中,特别适合使用硅晶圆、铜箔。
隔着规定的图案的光掩模对涂布在上述基材上的本实施方式的感光性树脂组合物照射光(通常使用紫外线)。照射后,利用显影液将未曝光部溶解去除,得到期望的浮雕图案。
紫外线照射量优选累积照射量为500~8000mJ/cm2。
使用本实施方式的感光性树脂组合物的树脂图案形成方法中,作为显影液,优选使用有机溶剂。显影液只要使本实施方式的感光性树脂组合物溶解就没有特别限定。具体而言,可以举出N-甲基-2-吡咯烷酮、N-乙酰基-2-吡咯烷酮、N-苄基-2-吡咯烷酮、N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、二甲基亚砜、六甲基磷三酰胺、N-乙酰基-ε-己内酰胺、二甲基咪唑烷酮、二乙二醇二甲醚、三乙二醇二甲醚、γ-丁内酯等作为适合例。
这些显影液可以单独使用,也可以组合2种以上而使用。
将通过显影而形成的浮雕图案接着利用冲洗液进行清洗,将显影溶剂去除。冲洗液中,可以举出与显影液的混合性良好的甲醇、乙醇、异丙醇、水等作为适合例。
对通过上述处理得到的浮雕图案在选自80~250℃的范围中的温度下进行加热处理,将溶剂干燥,可以得到使本实施方式的感光性树脂组合物固化而成的固化膜。根据本实施方式,由于使用优异的显影性,即、曝光部充分固化、未曝光部被充分去除的树脂组合物,因而得到的浮雕图案可以以高分辨率获得。
对于使本实施方式的感光性树脂组合物固化而成的固化膜,具体而言,在波长365nm下的曝光量1500~2500mJ/cm2的条件下曝光后的未曝光部残膜率优选45%以下、更优选40%以下、进一步优选30%以下、更进一步优选10%以下。上述曝光光源没有特别限定,例如可以使用高压汞灯,以在365nm下成为上述曝光量的方式进行曝光。
本说明书中,“未曝光部残膜率”是指,由以下定义算出的值。测定方法的详情在实施例中详述。
未曝光部残膜率(%)=[未曝光部的显影后的质量/未曝光部的显影前的质量]×100
使本实施方式的感光性树脂组合物固化而成的固化膜的曝光部残膜率优选70%以上、更优选80%以上、进一步优选85%以上。
本说明书中,“曝光部残膜率”是指,由以下定义算出的值。测定方法的详情在实施例中详述。
曝光部残膜率(%)=[曝光部的显影后的质量/曝光部的显影前的质量]×100
通过本实施方式得到的固化膜的膜厚优选10~85μm。膜厚如果处于上述范围,则可以用作优异的绝缘性膜。膜厚越厚(即,涂布于基材的感光性树脂组合物量越增加),特别是聚酰亚胺树脂的溶剂溶解性上产生问题的情况越多。然而,根据本发明,通过使用具有特定结构和特定末端结构、且具有特定的分子量范围的聚酰亚胺树脂,从而上述情况下,也可以兼顾优异的溶解溶剂性与透明性。
因此,本实施方式的固化膜例如可以在假定施加高的电压的绝缘性膜用途中适合使用。由包含具有特定结构和特定末端结构、且具有特定的分子量的聚酰亚胺树脂(A)的本实施方式的感光性树脂组合物得到的固化膜可以有效地抑制裂纹等的发生,物性优异。
[用途]
本实施方式的感光性树脂组合物和固化膜可以用于各种用途。例如可以适合用于电子设备的半导体元件的表面保护膜、层间绝缘膜、电路基板的布线保护绝缘膜、特别是高密度化、高集成化后的上述用途。
实施例
以下,根据实施例和比较例对本发明更详细地进行说明,但本发明不受这些实施例的任何限定。
本实施例和比较例中采用的评价方法如以下所述。
(1)重均分子量和数均分子量
通过GPC分析,求出重均分子量(Mw)和数均分子量(Mn)。分析中使用的装置和分析条件如下述。
装置:Viscotek TDAmax(Malvern Panalytical Ltd.制)
柱:A6000M×2(Malvern Panalytical Ltd.制)
洗脱液:添加有20mM溴化锂的二甲基甲酰胺
流速:1.0ml/分钟
柱温:40℃
检测器:RI(折射率检测器)、RALS(光散射检测器)、LALS(光散射检测器)
(2)未曝光部的残膜率(%)
以下中记载的实施例和比较例中,制备含有包含聚酰亚胺树脂的感光性树脂组合物的清漆。用旋涂机,在硅晶圆上涂布各实施例和比较例中分别得到的清漆后,在100℃下加热60分钟,将溶剂去除。将该时刻(上述条件下去除溶剂的时刻)的清漆的质量作为未曝光部的显影前质量。使其浸渍于显影液的γ-丁内酯5分钟后,使用甲醇作为冲洗液进行清洗,在空气流通下去除溶剂直至质量变化消失为止。将该溶剂去除后残留于硅晶圆上的膜的质量作为未曝光部的显影后质量,根据下述式求出未曝光部残膜率。
未曝光部残膜率(%)=[未曝光部的显影后的质量/未曝光部的显影前的质量]×100
(3)曝光部的残膜率(%)
以下中记载的实施例和比较例中,制备含有包含聚酰亚胺树脂的感光性树脂组合物的清漆。用旋涂机,在硅晶圆上涂布各实施例和比较例中分别得到的清漆后,在100℃下加热60分钟,将溶剂去除。将该时刻(上述条件下去除溶剂的时刻)的清漆的质量作为曝光部的显影前质量。进行UV照射,使其浸渍于显影液的γ-丁内酯5分钟后,使用甲醇作为冲洗液进行清洗,在空气流通下去除溶剂直至质量变化消失为止。将该溶剂去除后残留于硅晶圆上的膜的质量作为曝光部的显影后质量,根据下述式求出残膜率。
曝光部残膜率(%)=[曝光部的显影后的质量/曝光部的显影前的质量]×100
上述(2)和(3)的显影时使用的装置和条件如下述。
紫外线照射装置:ECS-1511U(Eyegraphics株式会社制)
光源:高压汞灯
照度:670~700mW/cm2
累积光量:2400mJ/cm2
显影液:γ-丁内酯
显影时间:5分钟
冲洗液:甲醇
硅晶圆:4英寸硅晶圆(Advantec Co.,Ltd.制)
合成例1
在具备氮气导入管、搅拌装置、温度计、冷凝器的500ml的五口烧瓶中,在氮气导入下,投入1,4-双[2-(4-氨基苯基)-2-丙基]苯(以下,BiS-AP)97.279g(0.28mol)、1-(4-氨基苯基)-2,3-二氢-1,3,3-三甲基-1H-茚-5-胺(以下,TMDA)32.141g(0.12mol)、三乙胺(以下,TEA)18.754g(0.19mol)、三乙二胺(以下,TEDA)0.083g(0.74mmol)、γ-丁内酯(以下,GBL)259.7g,边搅拌边加热至70℃。向其中加入1,2,4,5-环己烷四羧酸二酐(以下,HPMDA)82.943g(0.37mol),在180℃下反应5小时。用N,N-二甲基乙酰胺(以下,DMAc)536.8g稀释,得到固体成分浓度20质量%的聚酰亚胺清漆995g。GPC下的测定的结果,本合成例中得到的聚酰亚胺的重均分子量为15800。
合成例2
使BiS-AP量为93.921g(0.27mol)、TMDA量为31.126g(0.12mol)、TEA量为18.72g(0.19mol)、TEDA量为0.083g(0.74mmol)、GBL量为254.8g、和DMAc量为524.3g,除此之外,与合成例1同地样地得到聚酰亚胺清漆973g。GPC下的测定的结果,本合成例中得到的聚酰亚胺的重均分子量为27000。
合成例3
使BiS-AP量为92.462g(0.27mol)、TMDA量为30.642g(0.12mol)、TEA量为18.72g(0.19mol)、TEDA量为0.083g(0.74mmol)、GBL量为252.4g、和DMAc量为519.3g,除此之外,与合成例1同地样地得到聚酰亚胺清漆964g。GPC下的测定的结果,本合成例中得到的聚酰亚胺的重均分子量为33200。
合成例4
使BiS-AP量为91.513g(0.27mol)、TMDA量为30.327g(0.11mol)、TEA量为18.72g(0.19mol)、TEDA量为0.083g(0.74mmol)、GBL量为250.9g、和DMAc量为516.1g,除此之外,与合成例1同地样地得到聚酰亚胺清漆959g。GPC下的测定的结果,本合成例中得到的聚酰亚胺的重均分子量为42800。
合成例5
使BiS-AP量为90.401g(0.26mol)、TMDA量为29.959g(0.11mol)、TEA量为18.72g(0.19mol)、TEDA量为0.083g(0.74mmol)、GBL量为249.0g、和DMAc量为512.3g,除此之外,与合成例1同地样地得到聚酰亚胺清漆952g。GPC下的测定的结果,本合成例中得到的聚酰亚胺的重均分子量为75600。
合成例6
使BiS-AP量为0.00g(0.00mol)、TMDA量为103.720g(0.39mol)、TEA量为1.871g(0.018mol)、TEDA量为0.0g(0.00mmol)、GBL量为228.3g、和DMAc量为464.1g,除此之外,与合成例1同地样地得到聚酰亚胺清漆865g。GPC下的测定的结果,本合成例中得到的聚酰亚胺的重均分子量为14000。
合成例7
使BiS-AP量为0.00g(0.00mol)、TMDA量为0.00g(0.00mol),加入作为芳香族二胺的4,4’-氧双[3-(三氟甲基)苯胺](以下,6FODA)130.950g(0.39mol),使TEA量为1.871g(0.018mol)、TEDA量为0.0g(0.00mmol)、GBL量为261.6g、和DMAc量为539.7g,除此之外,与合成例1同地样地得到聚酰亚胺清漆1002g。GPC下的测定的结果,本合成例中得到的聚酰亚胺的重均分子量为23100。
合成例8
使BiS-AP量为0.00g(0.00mol)、TMDA量为31.13g(0.12mol),加入作为芳香族二胺的1,3-双[2-(4-氨基苯基)-2-丙基]苯(以下,BiS-AM)93.92g(0.27mol),使TEA量为21.248g(0.21mol)、TEDA量为0.094g(0.83mmol)、GBL量为254.6g、和DMAc量为525.4g,除此之外,与合成例1同地样地得到聚酰亚胺清漆975g。GPC下的测定的结果,本合成例中得到的聚酰亚胺的重均分子量为28100。
将上述合成例1~8中得到的聚酰亚胺树脂的平均分子量归纳于表1。
[表1]
表1
实施例1
放入合成例1中得到的聚酰亚胺清漆160g、丙烯酸2-异氰酸根合乙酯(昭和电工株式会社制,KarenzAOI)4.95g、对甲氧基苯酚(以下,MEHQ)0.05g,在50℃下反应5小时。之后,在水中滴加反应液,使聚酰亚胺析出,在70℃下干燥一晚,得到聚酰亚胺树脂(A)。使该聚酰亚胺树脂(A)3g溶解于GBL10g,加入三羟甲基丙烷三丙烯酸酯(TMP-TA)0.75g、1-羟基环己基苯基酮(BASF株式会社制,IRGACURE184)0.045g、双(2,4,6-三甲基苯甲酰基)苯基氧化膦(BASF株式会社制,IRGACURE819)0.105g,进行搅拌直至溶解,得到感光性树脂组合物(感光性树脂清漆)。将该感光性树脂组合物涂布于硅晶圆上,在100℃下干燥60分钟。然后,浸渍于GBL5分钟,用甲醇冲洗,在空气流通下去除溶剂直至质量变化消失,算出未曝光部残膜率。此时的未曝光部残膜率为0%。另外,将感光性树脂组合物涂布于硅晶圆上,在100℃下干燥60分钟后,使用Eyegraphics株式会社制Eye Mini Grantage(ECS-1511U),光源使用高压汞灯,在曝光波长365nm下的曝光量1500~2500mJ/cm2的条件下进行曝光,形成固化膜,然后,浸渍于GBL5分钟,用甲醇冲洗,在空气流通下去除溶剂直至质量变化消失,算出曝光部残膜率。此时的曝光部残膜率为100%。将结果示于表2。
实施例2~9和比较例1
制成下述表所示的配方,除此之外,与上述实施例1同样地制备感光性树脂组合物,评价其特性。将结果一并示于表2。
[表2]
表2
*1:1,1-双(丙烯酰氧基甲基)乙基异氰酸酯(昭和电工株式会社制、Karenz BEI)
*2:二季戊四醇六丙烯酸酯
与比较例1相比可知,包含本实施方式的感光性树脂组合物的固化膜具有优异的显影性。还确认了包含本实施方式的感光性树脂组合物的固化膜不产生裂纹。
Claims (13)
1.一种感光性树脂组合物,其包含聚酰亚胺树脂(A),所述聚酰亚胺树脂(A)具有下述通式(1)所示的结构、且重均分子量为70000以下,
通式(1)中,R为具有环状结构、具有非环状结构、或具有环状结构和非环状结构的碳数4~10的4价的基团;A具有选自由脂肪族烃基、脂环式烃基、芳香族烃基、和有机硅氧烷基组成的组中的至少1种基团、且为碳数2~39的2价的基团;在A的主链上任选插入有选自由-O-、-SO2-、-CO-、-CH2-、-C(CH3)2-、-C2H4O-、和-S-组成的组中的至少1种基团;n表示重复单元数;通式(1)的末端为下述式(2)或式(3)所示的基团、或氢原子中的任意者,且末端的至少一者为式(2)或式(3)所示的基团,
通式(2)和(3)中,X和X2各自独立地为碳数2~15的基团,X和X2任选具有选自由酯键和双键组成的组中的至少1个基团,Y和Y2各自独立地为氢原子或甲基。
2.根据权利要求1所述的感光性树脂组合物,其中,所述聚酰亚胺树脂(A)的重均分子量为5000以上。
3.根据权利要求1或2所述的感光性树脂组合物,其中,所述聚酰亚胺树脂(A)在波长200~400nm下的透光率为50%以上。
4.根据权利要求1~3中任一项所述的感光性树脂组合物,其中,在波长365nm下的曝光量1500~2500mJ/cm2的条件下曝光后的未曝光部的残膜率为40%以下。
5.根据权利要求1~4中任一项所述的感光性树脂组合物,其中,所述通式(1)中的A包含芳香环作为芳香族烃基。
7.根据权利要求1~6中任一项所述的感光性树脂组合物,其中,所述聚酰亚胺树脂(A)包含由4,4’-二氨基-2,2’-双(三氟甲基)联苯、1-(4-氨基苯基)-2,3-二氢-1,3,3-三甲基-1H-茚-5-胺、4,4’-氧双[3-(三氟甲基)苯胺]、或1,3-双[2-(4-氨基苯基)-2-丙基]苯构成的单元中的至少1种。
8.根据权利要求1~7中任一项所述的感光性树脂组合物,其中,还包含选自由光聚合引发剂、溶剂、和光聚合性化合物组成的组中的至少1种。
9.根据权利要求8所述的感光性树脂组合物,其中,所述光聚合性化合物为多官能自由基聚合性单体。
10.根据权利要求1~9中任一项所述的感光性树脂组合物,其中,还包含敏化剂。
11.根据权利要求1~10中任一项所述的感光性树脂组合物,其用于绝缘膜的形成。
12.一种固化膜,其是使权利要求1~11中任一项所述的感光性树脂组合物固化而成的。
13.根据权利要求12所述的固化膜,其膜厚为10~85μm。
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