CN111205463B - 聚硅氧烷骨架聚合物、感光性树脂组合物、图案形成方法和光半导体器件的制造 - Google Patents
聚硅氧烷骨架聚合物、感光性树脂组合物、图案形成方法和光半导体器件的制造 Download PDFInfo
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- CN111205463B CN111205463B CN201911153444.8A CN201911153444A CN111205463B CN 111205463 B CN111205463 B CN 111205463B CN 201911153444 A CN201911153444 A CN 201911153444A CN 111205463 B CN111205463 B CN 111205463B
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- DCYQPMGIYRPCBA-UHFFFAOYSA-N [2,3-bis(trifluoromethylsulfonyloxy)phenyl] trifluoromethanesulfonate Chemical compound FC(F)(F)S(=O)(=O)OC1=CC=CC(OS(=O)(=O)C(F)(F)F)=C1OS(=O)(=O)C(F)(F)F DCYQPMGIYRPCBA-UHFFFAOYSA-N 0.000 description 1
- OIHCCWXZFYNOJS-UHFFFAOYSA-N [2,3-bis-(4-methylphenyl)sulfonyloxyphenyl] 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC1=CC=CC(OS(=O)(=O)C=2C=CC(C)=CC=2)=C1OS(=O)(=O)C1=CC=C(C)C=C1 OIHCCWXZFYNOJS-UHFFFAOYSA-N 0.000 description 1
- IORUEKDKNHHQAL-UHFFFAOYSA-N [2-tert-butyl-6-[(3-tert-butyl-2-hydroxy-5-methylphenyl)methyl]-4-methylphenyl] prop-2-enoate Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)OC(=O)C=C)=C1O IORUEKDKNHHQAL-UHFFFAOYSA-N 0.000 description 1
- JYSSGQITKNFRQE-UHFFFAOYSA-N [3-(4-anilinoanilino)-2-hydroxypropyl] 2-methylprop-2-enoate Chemical compound C1=CC(NCC(O)COC(=O)C(=C)C)=CC=C1NC1=CC=CC=C1 JYSSGQITKNFRQE-UHFFFAOYSA-N 0.000 description 1
- HKKMPPDCCCBZHM-UHFFFAOYSA-M [4-[(2-methylpropan-2-yl)oxy]phenyl]-diphenylsulfanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC(OC(C)(C)C)=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 HKKMPPDCCCBZHM-UHFFFAOYSA-M 0.000 description 1
- DBQJFJFPPMVQAF-UHFFFAOYSA-N [4-[[5-[cyano-(2-methylphenyl)methylidene]thiophen-2-ylidene]amino]oxysulfonylphenyl] 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC1=CC=C(S(=O)(=O)ON=C2C=CC(S2)=C(C#N)C=2C(=CC=CC=2)C)C=C1 DBQJFJFPPMVQAF-UHFFFAOYSA-N 0.000 description 1
- GLCCGSHEKBXUGH-UHFFFAOYSA-N [[5-[cyano-(2-methylphenyl)methylidene]thiophen-2-ylidene]amino] 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)ON=C(S1)C=CC1=C(C#N)C1=CC=CC=C1C GLCCGSHEKBXUGH-UHFFFAOYSA-N 0.000 description 1
- QFKJMDYQKVPGNM-UHFFFAOYSA-N [benzenesulfonyl(diazo)methyl]sulfonylbenzene Chemical compound C=1C=CC=CC=1S(=O)(=O)C(=[N+]=[N-])S(=O)(=O)C1=CC=CC=C1 QFKJMDYQKVPGNM-UHFFFAOYSA-N 0.000 description 1
- GLGXSTXZLFQYKJ-UHFFFAOYSA-N [cyclohexylsulfonyl(diazo)methyl]sulfonylcyclohexane Chemical compound C1CCCCC1S(=O)(=O)C(=[N+]=[N-])S(=O)(=O)C1CCCCC1 GLGXSTXZLFQYKJ-UHFFFAOYSA-N 0.000 description 1
- DUJLILQBTCLTDQ-UHFFFAOYSA-N [cyclopentylsulfonyl(diazo)methyl]sulfonylcyclopentane Chemical compound C1CCCC1S(=O)(=O)C(=[N+]=[N-])S(=O)(=O)C1CCCC1 DUJLILQBTCLTDQ-UHFFFAOYSA-N 0.000 description 1
- FEVJONIJUZTKGL-UHFFFAOYSA-N [tert-butylsulfonyl(diazo)methyl]sulfonylcyclohexane Chemical compound CC(C)(C)S(=O)(=O)C(=[N+]=[N-])S(=O)(=O)C1CCCCC1 FEVJONIJUZTKGL-UHFFFAOYSA-N 0.000 description 1
- 125000005075 adamantyloxy group Chemical group C12(CC3CC(CC(C1)C3)C2)O* 0.000 description 1
- 238000012644 addition polymerization Methods 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- CXJVMJWCNFOERL-UHFFFAOYSA-N benzenesulfonylsulfonylbenzene Chemical compound C=1C=CC=CC=1S(=O)(=O)S(=O)(=O)C1=CC=CC=C1 CXJVMJWCNFOERL-UHFFFAOYSA-N 0.000 description 1
- OSIVCXJNIBEGCL-UHFFFAOYSA-N bis(2,2,6,6-tetramethyl-1-octoxypiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)N(OCCCCCCCC)C(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)N(OCCCCCCCC)C(C)(C)C1 OSIVCXJNIBEGCL-UHFFFAOYSA-N 0.000 description 1
- UQWLFOMXECTXNQ-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)methylsulfonyl-trifluoromethane Chemical compound FC(F)(F)S(=O)(=O)[C-](S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F UQWLFOMXECTXNQ-UHFFFAOYSA-N 0.000 description 1
- WTXDNMDDFAESOT-UHFFFAOYSA-M bis[4-[(2-methylpropan-2-yl)oxy]phenyl]-phenylsulfanium;4-methylbenzenesulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.C1=CC(OC(C)(C)C)=CC=C1[S+](C=1C=CC(OC(C)(C)C)=CC=1)C1=CC=CC=C1 WTXDNMDDFAESOT-UHFFFAOYSA-M 0.000 description 1
- SSCOHVUVCBYNFB-UHFFFAOYSA-M bis[4-[(2-methylpropan-2-yl)oxy]phenyl]-phenylsulfanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC(OC(C)(C)C)=CC=C1[S+](C=1C=CC(OC(C)(C)C)=CC=1)C1=CC=CC=C1 SSCOHVUVCBYNFB-UHFFFAOYSA-M 0.000 description 1
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- QDHFHIQKOVNCNC-UHFFFAOYSA-M butane-1-sulfonate Chemical compound CCCCS([O-])(=O)=O QDHFHIQKOVNCNC-UHFFFAOYSA-M 0.000 description 1
- QPXMRCTYZIAUQD-UHFFFAOYSA-M butane-1-sulfonate;triphenylsulfanium Chemical compound CCCCS([O-])(=O)=O.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 QPXMRCTYZIAUQD-UHFFFAOYSA-M 0.000 description 1
- QDHFHIQKOVNCNC-UHFFFAOYSA-N butane-1-sulfonic acid Chemical compound CCCCS(O)(=O)=O QDHFHIQKOVNCNC-UHFFFAOYSA-N 0.000 description 1
- TWIZJXCPYWDRNA-UHFFFAOYSA-N butanedioic acid 1-(2-hydroxyethyl)-2,2,3,5,6,6-hexamethylpiperidin-4-ol Chemical compound C(CCC(=O)O)(=O)O.CC1C(N(C(C(C1O)C)(C)C)CCO)(C)C TWIZJXCPYWDRNA-UHFFFAOYSA-N 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 229940043232 butyl acetate Drugs 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- ODOYKCYDOVBTAR-UHFFFAOYSA-N cyclohexylsulfonylsulfonylcyclohexane Chemical compound C1CCCCC1S(=O)(=O)S(=O)(=O)C1CCCCC1 ODOYKCYDOVBTAR-UHFFFAOYSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- OVLXQLQBOCAFDH-UHFFFAOYSA-M dicyclohexyl(phenyl)sulfanium;4-methylbenzenesulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.C1CCCCC1[S+](C=1C=CC=CC=1)C1CCCCC1 OVLXQLQBOCAFDH-UHFFFAOYSA-M 0.000 description 1
- NSXRYFKEEKGLHO-UHFFFAOYSA-M dicyclohexyl(phenyl)sulfanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1CCCCC1[S+](C=1C=CC=CC=1)C1CCCCC1 NSXRYFKEEKGLHO-UHFFFAOYSA-M 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- SXHRYKLRBLHUPL-UHFFFAOYSA-M dimethyl(phenyl)sulfanium;4-methylbenzenesulfonate Chemical compound C[S+](C)C1=CC=CC=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 SXHRYKLRBLHUPL-UHFFFAOYSA-M 0.000 description 1
- CYQUIWZGOBANMJ-UHFFFAOYSA-M dimethyl(phenyl)sulfanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C[S+](C)C1=CC=CC=C1 CYQUIWZGOBANMJ-UHFFFAOYSA-M 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- SBQIJPBUMNWUKN-UHFFFAOYSA-M diphenyliodanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C=1C=CC=CC=1[I+]C1=CC=CC=C1 SBQIJPBUMNWUKN-UHFFFAOYSA-M 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 235000019285 ethoxyquin Nutrition 0.000 description 1
- BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 description 1
- 229940117360 ethyl pyruvate Drugs 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
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- 239000011737 fluorine Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000003106 haloaryl group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 1
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- 230000005764 inhibitory process Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
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- 239000011630 iodine Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- JIQNWFBLYKVZFY-UHFFFAOYSA-N methoxycyclohexatriene Chemical compound COC1=C[C]=CC=C1 JIQNWFBLYKVZFY-UHFFFAOYSA-N 0.000 description 1
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- ORECYURYFJYPKY-UHFFFAOYSA-N n,n'-bis(2,2,6,6-tetramethylpiperidin-4-yl)hexane-1,6-diamine;2,4,6-trichloro-1,3,5-triazine;2,4,4-trimethylpentan-2-amine Chemical compound CC(C)(C)CC(C)(C)N.ClC1=NC(Cl)=NC(Cl)=N1.C1C(C)(C)NC(C)(C)CC1NCCCCCCNC1CC(C)(C)NC(C)(C)C1 ORECYURYFJYPKY-UHFFFAOYSA-N 0.000 description 1
- LKTCWOYIQVKYIV-UHFFFAOYSA-N n-butyl-4-chloro-n-(1,2,2,6,6-pentamethylpiperidin-4-yl)-1,3,5-triazin-2-amine Chemical compound N=1C=NC(Cl)=NC=1N(CCCC)C1CC(C)(C)N(C)C(C)(C)C1 LKTCWOYIQVKYIV-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000005246 nonafluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- MBAUOPQYSQVYJV-UHFFFAOYSA-N octyl 3-[4-hydroxy-3,5-di(propan-2-yl)phenyl]propanoate Chemical compound OC1=C(C=C(C=C1C(C)C)CCC(=O)OCCCCCCCC)C(C)C MBAUOPQYSQVYJV-UHFFFAOYSA-N 0.000 description 1
- 238000010943 off-gassing Methods 0.000 description 1
- 125000005375 organosiloxane group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- CLSUSRZJUQMOHH-UHFFFAOYSA-L platinum dichloride Chemical compound Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- QBERHIJABFXGRZ-UHFFFAOYSA-M rhodium;triphenylphosphane;chloride Chemical compound [Cl-].[Rh].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 QBERHIJABFXGRZ-UHFFFAOYSA-M 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
- JAELLLITIZHOGQ-UHFFFAOYSA-N tert-butyl propanoate Chemical compound CCC(=O)OC(C)(C)C JAELLLITIZHOGQ-UHFFFAOYSA-N 0.000 description 1
- WUPCFMITFBVJMS-UHFFFAOYSA-N tetrakis(1,2,2,6,6-pentamethylpiperidin-4-yl) butane-1,2,3,4-tetracarboxylate Chemical compound C1C(C)(C)N(C)C(C)(C)CC1OC(=O)CC(C(=O)OC1CC(C)(C)N(C)C(C)(C)C1)C(C(=O)OC1CC(C)(C)N(C)C(C)(C)C1)CC(=O)OC1CC(C)(C)N(C)C(C)(C)C1 WUPCFMITFBVJMS-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 238000005382 thermal cycling Methods 0.000 description 1
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- QXTIBZLKQPJVII-UHFFFAOYSA-N triethylsilicon Chemical compound CC[Si](CC)CC QXTIBZLKQPJVII-UHFFFAOYSA-N 0.000 description 1
- AANIRNIRVXARSN-UHFFFAOYSA-M trifluoromethanesulfonate;trimethylsulfanium Chemical compound C[S+](C)C.[O-]S(=O)(=O)C(F)(F)F AANIRNIRVXARSN-UHFFFAOYSA-M 0.000 description 1
- TUODWSVQODNTSU-UHFFFAOYSA-M trifluoromethanesulfonate;tris[4-[(2-methylpropan-2-yl)oxy]phenyl]sulfanium Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC(OC(C)(C)C)=CC=C1[S+](C=1C=CC(OC(C)(C)C)=CC=1)C1=CC=C(OC(C)(C)C)C=C1 TUODWSVQODNTSU-UHFFFAOYSA-M 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- FAYMLNNRGCYLSR-UHFFFAOYSA-M triphenylsulfonium triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 FAYMLNNRGCYLSR-UHFFFAOYSA-M 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000004260 weight control Methods 0.000 description 1
- 239000011995 wilkinson's catalyst Substances 0.000 description 1
- UTODFRQBVUVYOB-UHFFFAOYSA-P wilkinson's catalyst Chemical compound [Cl-].C1=CC=CC=C1P(C=1C=CC=CC=1)(C=1C=CC=CC=1)[Rh+](P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 UTODFRQBVUVYOB-UHFFFAOYSA-P 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
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Abstract
本发明提供聚硅氧烷骨架聚合物、感光性树脂组合物、图案形成方法和光半导体器件的制造。提供了聚合物，其在主链中包含聚硅氧烷、硅亚苯基、异氰脲酸和降冰片烯骨架并在侧链中具有环氧基团。涂覆包含该聚合物和光致产酸剂的感光性树脂组合物以形成膜，可使用具有大幅变化波长的辐照使膜图案化。图案化的膜具有高透明性、耐光性和耐热性。
Description
相关申请的交叉引用
本非临时申请按照35 U.S.C.§119(a)要求分别于2018年11月22日和2019年4月26日在日本提交的专利申请号2018-218755和2019-084911的优先权，其全部内容通过引用并入本文。
技术领域
本发明涉及聚硅氧烷骨架聚合物、感光性树脂组合物、图案形成方法和光半导体器件的制造方法。
背景技术
迄今，环氧树脂主要被用作光学器件(通常为发光二极管(LED)和CMOS图像传感器)的封装/保护材料。尤其是因为高透明性和耐光性，大多数使用环氧改性的有机硅树脂。例如，从专利文献1已知具有在硅亚苯基结构中引入脂环族环氧基团的有机硅树脂。
常规的封装/保护材料满足现有技术器件所需要的耐光性水平，但是未能满足先进光学器件例如LED(其目前被设计成产生较高输出)所需要的耐光性水平。它们还受到脱气和变色的困扰。现在，通过微加工技术来生产许多类型的光学器件。出于微加工目的，使用如以环氧树脂系材料为代表的各种抗蚀剂材料。然而，这些材料不适合微加工至10μm量级的尺寸。作为可用作抗蚀剂材料的环氧树脂材料，专利文献2公开了包含环氧树脂和双末端脂环族环氧改性的硅亚苯基交联剂的组合物。出于更高透明性的目的，这种组合物在耐热性和耐光性方面仍然不足。需要组合物用于形成能够经受更严苛条件的膜。
引用列表
专利文献1：JP-B H08-32763(USP 4,990,546)
专利文献2：JP-A 2012-001668(USP 8,715,905、EP 2397508)
发明内容
本发明的目的是提供新的聚合物，其能够形成具有高透明性和耐光性的膜；提供感光性树脂组合物，其能够使用具有大幅变化波长的辐照来形成图案，并形成具有高透明性、耐光性和耐热性的图案化的膜；提供使用该树脂组合物的图案形成方法；和提供光半导体器件的制造方法。
发明人发现了在主链中包含聚硅氧烷、硅亚苯基、异氰脲酸和降冰片烯骨架并在侧链中具有环氧基团的聚合物提供具有高透明性和耐光性的膜，发现了包含该聚合物和光致产酸剂的感光性树脂组合物有效的形成膜，由此可使用具有大幅变化波长的辐照来形成细微尺寸图案并且发现了图案化的膜表现出高透明性、耐光性和耐热性。
在一方面，本发明提供在主链中包含聚硅氧烷骨架、硅亚苯基骨架、异氰脲酸骨架和降冰片烯骨架并在侧链中具有环氧基团的聚合物。
优选地，具有10μm厚度的聚合物的膜相对于405nm波长的光而言具有至少95％的透过率。
在优选实施方案中，聚合物包含具有以下式(A1)至(A4)的重复单元。
本文中R1至R4各自独立地为C1-C20一价烃基，其可含有杂原子，m各自独立地为1至600的整数，条件是当m是至少2的整数时，基团R3可为相同的或不同的并且基团R4可为相同的或不同的，a1、a2、a3和a4是在以下范围的数：0<a1<1、0<a2<1、0<a3<1、0<a4<1，和a1+a2+a3+a4＝1。X1是具有式(X1)的二价基团：
其中R11和R12各自独立地为氢或甲基，n1和n2各自独立地为0至7的整数，R13是C1-C8二价烃基，其中碳原子之间可插入酯键或醚键。X2是具有式(X2)的二价基团：
其中R21和R22各自独立地为氢或C1-C20烷基基团，其可含有杂原子，并且k是0至10的整数。
在优选实施方案中，m是8至100的整数，R21和R22是氢，并且k为0。
在优选实施方案中，聚合物具有3,000至500,000的Mw。
在另一方面，本发明提供感光性树脂组合物，包含(A)以上限定的聚合物和(B)光致产酸剂，具体地100重量份的组分(A)和0.05至20重量份的组分(B)。
感光性树脂组合物可还包含(C)阳离子聚合性交联剂、(D)溶剂、和/或(E)抗氧化剂。
在另外的方面，本发明提供图案形成方法，包括以下步骤：
(i)涂覆以上限定的感光性树脂组合物至基板上以在其上形成感光性树脂膜，
(ii)使感光性树脂膜暴露于辐照，和
(iii)用显影剂使曝光的树脂膜显影。
在仍然另外的方面，本发明提供光半导体器件的制造方法，包括以上限定的图案形成方法，该器件包含图案化的感光性树脂膜。
有益效果
本发明的聚合物容易合成并且提供具有高透明性和耐光性的膜。包含该聚合物和光致产酸剂的感光性树脂组合物在不经历氧阻害的情况下有效地涂覆以形成膜。可通过使其暴露于具有大幅变化波长的辐照由该膜形成细微尺寸图案。感光性树脂组合物的膜表现出优异的透明性、耐光性和耐热性并因此在与光学器件等有关的保护和封装应用中是有效的。
具体实施方式
符号(Cn-Cm)意指每个基团含有n-m个碳原子的基团。“任选的”或“任选地/任选”意指随后描述的事件或情况可能发生或可能不发生，并且该描述包括该事件或情况发生的情况和不发生的情况。PAG表示光致产酸剂。
聚硅氧烷骨架聚合物
本发明的一种实施方案是在主链中包含聚硅氧烷骨架、硅亚苯基骨架、异氰脲酸骨架和降冰片烯骨架并在侧链中具有环氧基团的聚合物。
优选的聚合物被限定为包含具有以下式(A1)至(A4)的重复单元，其被简单地称作重复单元(A1)至(A4)。
在式(A2)和(A4)中，R1至R4各自独立地为C1-C20一价烃基，其可含有杂原子，m各自独立地为1至600的整数。当m是至少2的整数时，基团R3可为相同的或不同的并且基团R4可为相同的或不同的。在重复单元(A2)和(A4)中，包括至少两个硅氧烷单元时，该硅氧烷单元可全部是相同的，或者可包括至少两种不同的硅氧烷单元。包括至少两种不同的硅氧烷单元时(即m是至少2的整数)，可无规地或交替地结合硅氧烷单元或者可包括多个每个由相同的硅氧烷构成的嵌段。
一价烃基可为直链的、支化的或环状的，并且包括一价脂肪族烃基例如C1-C20烷基基团和C2-C20烯基基团，和一价芳香烃基例如C6-C20芳基基团和C7-C20芳烷基基团。
适合的烷基基团包括甲基、乙基、正丙基、异丙基、环丙基、正丁基、异丁基、仲丁基、叔丁基、环丁基、正戊基、环戊基、正己基、环己基、正庚基、正辛基、正壬基、正癸基、降冰片基和金刚烷基。适合的烯基基团包括乙烯基、丙烯基、丁烯基和戊烯基。
一价脂肪族烃基可含有杂原子。具体地，在一价脂肪族烃基中，部分或所有的氢原子可被卤素原子例如氟、氯、溴和碘取代，或者碳原子之间可插入羰基部分、醚键或硫醚键。典型的含有杂原子的脂肪族烃基是2-氧代环己基。
适合的芳基基团包括苯基、2-甲基苯基、3-甲基苯基、4-甲基苯基、2-乙基苯基、3-乙基苯基、4-乙基苯基、4-叔丁基苯基、4-丁基苯基、二甲基苯基、萘基、联苯基和三联苯基。适合的芳烷基基团包括苯甲基和苯乙基。
一价芳香烃基可含有杂原子。具体地，在一价芳香烃基中，部分或所有的氢原子可被C1-C10烷氧基、C1-C10烷硫基、C6-C20芳氧基或C6-C20芳硫基基团取代。
适合的C1-C10烷氧基基团包括甲氧基、乙氧基、正丙氧基、异丙氧基、环丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、环丁氧基、正戊氧基、环戊氧基、正己氧基、环己氧基、正庚氧基、正辛氧基、正壬氧基、正癸氧基、降冰片基氧基和金刚烷氧基。
适合的C1-C10烷硫基基团包括甲硫基、乙硫基、正丙硫基、异丙硫基、环丙硫基、正丁硫基、异丁硫基、仲丁硫基、叔丁硫基、环丁硫基、正戊硫基、环戊硫基、正己硫基、环己硫基、正庚硫基、正辛硫基、正壬硫基、正癸硫基、降冰片基硫基和金刚烷硫基。
适合的C6-C20芳氧基基团包括苯氧基、2-甲基苯氧基、3-甲基苯氧基、4-甲基苯氧基、2-乙基苯氧基、3-乙基苯氧基、4-乙基苯氧基、4-叔丁基苯氧基、4-丁基苯氧基、二甲基苯氧基、萘氧基、联苯氧基和三联苯氧基。
适合的C6-C20芳硫基基团包括苯硫基、2-甲基苯硫基、3-甲基苯硫基、4-甲基苯硫基、2-乙基苯硫基、3-乙基苯硫基、4-乙基苯硫基、4-叔丁基苯硫基、4-丁基苯硫基、二甲基苯硫基、萘硫基、联苯硫基和三联苯硫基。
适合的取代芳基基团包括2-甲氧基苯基、3-甲氧基苯基、4-甲氧基苯基、2-乙氧基苯基、3-乙氧基苯基、4-乙氧基苯基、3-叔丁氧基苯基、4-叔丁氧基苯基、联苯基氧基苯基和联苯硫基苯基。
一价脂肪族烃基优选具有1-10个碳原子、更优选1-8个碳原子。一价芳香烃基优选具有6-14个碳原子、更优选6-10个碳原子。
前述基团中，R1至R4优选选自甲基、乙基、正丙基和苯基，更优选甲基和苯基。
在式(A2)和(A4)中，m各自独立地为1至600、优选8至100的整数。
在式(A1)至(A4)中，a1、a2、a3和a4是在以下范围中的数：0<a1<1、0<a2<1、0<a3<1、0<a4<1，和a1+a2+a3+a4＝1；
优选地0.010≤a1+a2≤0.490、0.010≤a3+a4≤0.490、0.050≤a1+a3≤0.490、0.010≤a2+a4≤0.450，和a1+a2+a3+a4＝1；
更优选地0.050≤a1+a2≤0.450、0.050≤a3+a4≤0.450、0.100≤a1+a3≤0.475、0.025≤a2+a4≤0.400，和a1+a2+a3+a4＝1；
在式(A1)和(A2)中，X1是具有式(X1)的二价基团。
在式(X1)中，R11和R12各自独立地为氢或甲基，n1和n2各自独立地为0至7的整数。
在式(X1)中，R13是C1-C8二价烃基，其中碳原子之间可插入酯键或醚键。二价烃基可为直链的、支化的或环状的，并且它的实例包括烷二基基团例如亚甲基、乙烷-1,1-二基、乙烷-1,2-二基、丙烷-1,2-二基、丙烷-1,3-二基、丁烷-1,2-二基、丁烷-1,3-二基和丁烷-1,4-二基。在二价烃基中，碳原子之间可插入酯键或醚键。尤其是R13优选为亚甲基或亚乙基，其中亚甲基是更优选的。
在式(A3)和(A4)中，X2是具有式(X2)的二价基团。
在式(X2)中，R21和R22各自独立地为氢或可含有杂原子的C1-C20烷基基团。烷基基团的实例如以上对于R1至R4所列举的。R21和R22优选是氢或甲基。
在式(X2)中，k是0至10的整数，优选为0。
聚合物优选具有3,000至500,000、更优选5,000至200,000的重均分子量(Mw)。具有在该范围内的Mw的聚合物是固体并具有膜形成能力。整个公开内容中，通过凝胶渗透色谱法(GPC)使用四氢呋喃(THF)作为洗脱液相对于聚苯乙烯标准物测量Mw。
在聚合物中，可无规地或交替地结合重复单元(A1)至(A4)，并且可包括多个每个由相同的单元构成的嵌段。聚合物优选具有10至90重量％的硅氧烷单元含量。
制备聚硅氧烷骨架聚合物
可通过组合具有式(1)的化合物、具有式(2)的化合物、具有式(3)的化合物和具有式(4)的化合物，并在金属催化剂的存在下进行加成聚合来制备该聚合物。特别是，这些化合物被简单地称作化合物(1)、(2)、(3)和(4)。
此处如以上定义R1至R4、R11至R13、R21、R22、m、n1、n2和k。
本文使用的金属催化剂的实例包括铂族金属单质例如铂(包括铂黑)、铑和钯；氯化铂、氯铂酸和氯铂酸盐例如H2PtCl4·xH2O、H2PtCl6·xH2O、NaHPtCl6·xH2O、KHPtCl6·xH2O、Na2PtCl6·xH2O、K2PtCl4·xH2O、PtCl4·xH2O、PtCl2和Na2HPtCl4·xH2O，其中x优选为0至6的整数，更优选为0或6；如USP3,220,972中描述的醇改性的氯铂酸；如USP3,159,601、USP3,159,662和USP3,775,452中描述的氯铂酸-烯烃络合物；包含铂族金属的负载型催化剂例如在氧化铝、氧化硅和碳载体上的铂黑和钯；铑-烯烃络合物；氯三(三苯基膦)合铑(已知为Wilkinson’s催化剂)；和氯化铂、氯铂酸和氯铂酸盐与含乙烯基的硅氧烷、特别是含乙烯基的环硅氧烷的络合物。
以催化量使用催化剂，其优选为基于化合物(1)至(4)的总重量0.001至0.1重量％的铂族金属。
在聚合反应中，如果需要可使用溶剂。适合的溶剂是烃溶剂例如甲苯和二甲苯。反应温度优选在40至150℃、更优选60至120℃的范围内，在该范围内催化剂未失活，并且聚合可在短时间内完成。聚合时间随着起始化合物的类型和量变化。优选为约0.5至约100小时，更优选约0.5至约30小时用于防止水分进入聚合体系中。在反应完成之后，蒸馏掉溶剂(如果使用)，于是获得了聚合物。
没有特别限制反应工序。优选的工序是通过首先混合化合物(3)和(4)，加热，添加金属催化剂至混合物并然后在0.1至5小时中滴加化合物(1)和(2)。
在聚合反应中，优选以如下量组合起始化合物，该量使得化合物(1)和(2)中的氢甲硅烷基基团的总量与化合物(3)和(4)中的碳-碳双键的总量的摩尔比可在0.67-1.67、更优选0.83-1.25的范围。
可使用分子量控制试剂例如单烯丙基化合物(例如邻-烯丙基酚)、单氢硅烷(例如三乙基氢硅烷)或单氢硅氧烷来控制聚合物的Mw。
感光性树脂组合物
本发明的另一种实施方案是包含以上限定的(A)聚硅氧烷骨架聚合物和(B)光致产酸剂的感光性树脂组合物。可单独地或以混合物使用聚硅氧烷骨架化的聚合物(A)。
(B)光致产酸剂
没有特别限制作为组分(B)的光致产酸剂，只要它在曝光时分解产生酸，优选地它在暴露于190至500nm波长的光时分解产生酸。PAG(B)充当固化催化剂。适合的PAG包括
盐、重氮甲烷衍生物、乙二肟衍生物、β-酮砜衍生物、二砜衍生物、硝基苯甲基磺酸酯衍生物、磺酸酯衍生物、酰亚胺基(imidoyl)磺酸酯衍生物、肟磺酸酯衍生物、亚氨基磺酸酯衍生物和三嗪衍生物。
示例性
盐包括具有式(B1)的锍盐和具有式(B2)的碘
盐。
在式(B1)和(B2)中，R101至R105各自独立地为任选取代的C1-C12烷基基团、任选取代的C6-C12芳基基团或任选取代的C7-C12芳烷基基团。A-是非亲核的对离子。
烷基基团可为直链的、支化的或环状的并且包括例如甲基、乙基、正丙基、异丙基、环丙基、正丁基、异丁基、仲丁基、叔丁基、环丁基、正戊基、环戊基、环己基、降冰片基和金刚烷基。芳基基团包括苯基、萘基和联苯基。芳烷基基团包括苯甲基和苯乙基。在这些基团上适合的取代基包括氧代，直链的、支化的或环状C1-C12烷氧基，直链的、支化的或环状C1-C12烷基、C6-C24芳基、C7-C25芳烷基、C6-C24芳氧基和C6-C24芳硫基基团。
R101至R105的优选实例包括任选取代的烷基基团例如甲基、乙基、丙基、丁基、环己基、降冰片基、金刚烷基和2-氧代环己基；任选取代的芳基基团例如苯基、萘基、联苯基、邻-、间-或对-甲氧基苯基、乙氧基苯基、间-或对-叔丁氧基苯基、2-、3-或4-甲基苯基、乙基苯基、4-叔丁基苯基、4-丁基苯基、二甲基苯基、三联苯基、联苯基、氧基苯基和联苯基硫基苯基(biphenylylthiophenyl)；和任选取代的芳烷基基团例如苯甲基和苯乙基。这些中，任选取代的芳基基团和任选取代的芳烷基基团是更优选的。
非亲核的对离子的实例包括卤化物离子例如氯化物和溴化物；氟代烷磺酸根离子例如三氟甲磺酸根、1,1,1-三氟乙烷磺酸根、和九氟丁烷磺酸根；芳基磺酸根离子例如甲苯磺酸根、苯磺酸根、4-氟苯磺酸根和1,2,3,4,5-五氟苯磺酸根；烷磺酸根离子例如甲磺酸根和丁烷磺酸根；氟代烷磺酰亚胺离子例如三氟甲磺酰亚胺；氟代烷磺酰甲基化物离子例如三(三氟甲磺酰基)甲基化物；和硼酸根离子例如四苯基硼酸根和四(五氟苯基)硼酸根。
示例性重氮甲烷衍生物包括具有式(B3)的化合物。
在式(B3)中，R111和R112各自独立地为C1-C12烷基或卤代烷基基团、任选取代的C6-C12芳基基团或C7-C12芳烷基基团。
烷基基团可为直链的、支化的或环状的并且其实例如以上对于R101至R105所列举的。卤代烷基基团的实例包括三氟甲基、1,1,1-三氟乙基、1,1,1-三氯乙基和九氟丁基。
任选取代的芳基基团的实例包括苯基；烷氧基苯基基团例如2-、3-或4-甲氧基苯基、2-、3-或4-乙氧基苯基、3-或4-叔丁氧基苯基；烷基苯基基团例如2-、3-或4-甲基苯基、乙基苯基、4-叔丁基苯基、4-丁基苯基和二甲基苯基；和卤代芳基基团例如氟苯基、氯苯基和1,2,3,4,5-五氟苯基。芳烷基基团的实例包括苯甲基和苯乙基。
示例性乙二肟衍生物包括具有式(B4)的化合物。
在式(B4)中，R121至R124各自独立地为C1-C12烷基或卤代烷基基团、任选取代的C6-C12芳基基团或C7-C12芳烷基基团。R123和R124可结合在一起以与它们所连接的碳原子形成环。在形成环的情况下，R123与R124结合以形成C1-C12直链的或支化的亚烷基基团。
烷基、卤代烷基、任选取代的芳基和芳烷基基团的实例如以上对于R111和R112所列举的。直链的或支化的亚烷基基团的实例包括亚甲基、亚乙基、亚丙基、亚丁基和亚己基。
重氮甲烷衍生物的实例包括双(苯磺酰基)重氮甲烷，双(对甲苯磺酰基)重氮甲烷，双(二甲苯磺酰基)重氮甲烷，双(环己基磺酰基)重氮甲烷，双(环戊基磺酰基)重氮甲烷，双(正丁基磺酰基)重氮甲烷，双(异丁基磺酰基)重氮甲烷，双(仲丁基磺酰基)重氮甲烷，双(正丙基磺酰基)重氮甲烷，双(异丙基磺酰基)重氮甲烷，双(叔丁基磺酰基)重氮甲烷，双(正戊基磺酰基)重氮甲烷，双(异戊基磺酰基)重氮甲烷，双(仲戊基磺酰基)重氮甲烷，双(叔戊基磺酰基)重氮甲烷，1-环己基磺酰基-1-(叔丁基磺酰基)重氮甲烷，1-环己基磺酰基-1-(叔戊基磺酰基)重氮甲烷，和1-叔戊基磺酰基-1-(叔丁基磺酰基)重氮甲烷。
乙二肟衍生物的实例包括双-O-(对甲苯磺酰基)-α-二甲基乙二肟，双-O-(对甲苯磺酰基)-α-二苯基乙二肟，双-O-(对甲苯磺酰基)-α-二环己基乙二肟，双-O-(对甲苯磺酰基)-2,3-戊二酮乙二肟，双-O-(对甲苯磺酰基)-2-甲基-3,4-戊二酮乙二肟，双-O-(正丁烷磺酰基)-α-二甲基乙二肟，双-O-(正丁烷磺酰基)-α-二苯基乙二肟，双-O-(正丁烷磺酰基)-α-二环己基乙二肟，双-O-(正丁烷磺酰基)-2,3-戊二酮乙二肟，双-O-(正丁烷磺酰基)-2-甲基-3,4-戊二酮乙二肟，双-O-(甲磺酰基)-α-二甲基乙二肟，双-O-(三氟甲磺酰基)-α-二甲基乙二肟，双-O-(1,1,1-三氟乙磺酰基)-α-二甲基乙二肟，双-O-(叔丁烷磺酰基)-α-二甲基乙二肟，双-O-(全氟辛烷磺酰基)-α-二甲基乙二肟，双-O-(环己烷磺酰基)-α-二甲基乙二肟，双-O-(苯磺酰基)-α-二甲基乙二肟，双-O-(对-氟苯磺酰基)-α-二甲基乙二肟，双-O-(对-叔丁基苯磺酰基)-α-二甲基乙二肟，双-O-(二甲苯磺酰基)-α-二甲基乙二肟，和双-O-(樟脑磺酰基)-α-二甲基乙二肟。
β-酮砜衍生物的实例包括2-环己基羰基-2-(对甲苯磺酰基)丙烷和2-异丙基羰基-2-(对甲苯磺酰基)丙烷。
二砜衍生物的实例包括二苯基二砜和二环己基二砜。
硝基苯甲基磺酸酯衍生物的实例包括对甲苯磺酸2,6-二硝基苯甲酯和对甲苯磺酸2,4-二硝基苯甲酯。
磺酸酯衍生物的实例包括1,2,3-三(甲磺酰氧基)苯，1,2,3-三(三氟甲磺酰氧基)苯，和1,2,3-三(对甲苯磺酰氧基)苯。
酰亚胺基(imido-yl)磺酸酯衍生物的实例包括邻苯二甲酰亚胺基三氟甲磺酸酯，邻苯二甲酰亚胺基甲苯磺酸酯，5-降冰片烯-2,3-二羧基酰亚胺基三氟甲磺酸酯，5-降冰片烯-2,3-二羧基酰亚胺基甲苯磺酸酯，5-降冰片烯-2,3-二羧基酰亚胺基正丁基磺酸酯，和正三氟甲磺酰氧基萘酰亚胺。
典型的肟磺酸酯衍生物是α-(苯锍氧亚氨基)-4-甲基苯基乙腈。
亚氨基磺酸酯衍生物的实例包括(5-(4-甲基苯基)磺酰氧基亚氨基-5H-噻吩-2-亚基)-(2-甲基苯基)乙腈和(5-(4-(4-甲基苯基磺酰氧基)苯基磺酰氧基亚氨基)-5H-噻吩-2-亚基)-(2-甲基苯基)乙腈。同样2-甲基-2-[(4-甲基苯基)磺酰基]-1-[(4-甲基硫代)苯基]-1-丙烷是可用的。
作为PAG，
盐是优选的，其中锍盐是更优选的。
优选地以每100重量份的组分(A)0.05至20重量份、更优选0.1至5重量份的量使用PAG(B)。在该范围中的PAG量确保充足的光固化能力并且有效的防止厚膜的固化行为由于PAG本身的光吸收而劣化。为了获得本发明的透明性和耐光性特性，光吸收PAG(B)的量在确保光固化能力的范围内尽可能的小。可单独地或以混合物使用PAG。
(C)阳离子聚合性交联剂
感光性树脂组合物可还包含(C)阳离子聚合性交联剂。阳离子聚合性交联剂经历与组分(A)上的环氧基团的阳离子聚合反应以促进图案形成并起到提高光固化的树脂膜的强度的作用。
交联剂优选选自具有100至15,000、更优选200至1,000分子量的化合物。具有至少100分子量的化合物提供充足的光固化，而具有至多15,000分子量的化合物不使光固化的组合物的耐热性恶化。特别是，该化合物可为树脂或聚合物，并且在这种情况下，分子量是重均分子量(Mw)。
作为阳离子聚合性交联剂，具有选自以下官能团的化合物是优选的：环氧基、环氧丙烷基(oxetane)和乙烯基醚基团。可单独地或以混合物使用这样的化合物。
组分(C)的量为0至100重量份/100重量份的组分(A)，并且当使用时，优选为0.5至100重量份、更优选0.5至60重量份。当组分(C)的量为至少0.5份时，可获得曝光时充足的固化。当组分(C)的量为至多100份时，组合物中的组分(A)的比例没有减小，从而允许固化的组合物发挥期望的效果。可单独地或以混合物使用组分(C)。
(D)溶剂
可向感光性树脂组合物添加(D)溶剂以便促进涂覆操作。没有特别限制本文使用的溶剂(D)，只要组分(A)至(C)和其它添加剂(之后描述)可溶于其中。
优选的溶剂是有机溶剂。有机溶剂的说明性、非限制性的实例包括酮类例如环己酮、环戊酮和甲基-2-正戊酮；醇类例如3-甲氧基丁醇、3-甲基-3-甲氧基丁醇、1-甲氧基-2-丙醇和1-乙氧基-2-丙醇；醚类例如丙二醇单甲基醚(PGME)、乙二醇单甲基醚、丙二醇单乙基醚、乙二醇单乙基醚、丙二醇二甲基醚和二乙二醇二甲基醚；和酯类例如丙二醇单甲基醚乙酸酯(PGMEA)、丙二醇单乙基醚乙酸酯、乳酸乙酯、丙酮酸乙酯、乙酸丁酯、3-甲氧基丙酸甲酯、3-乙氧基丙酸乙酯、乙酸叔丁酯、丙酸叔丁酯、丙二醇单叔丁基醚乙酸酯和γ-丁内酯。可单独使用或两种或更多种组合使用这些溶剂。
这些溶剂中，优选的是乳酸乙酯、环己酮、环戊酮、PGMEA、γ-丁内酯、和它们的混合物，在其中PAG是最可溶的。
从树脂组合物的相容性和粘度观点来看，优选的是以50至2,000重量份、更优选50至1,000重量份和特别是50至100重量份/100重量份的组分(A)的量使用溶剂(D)。
(E)抗氧化剂
感光性树脂组合物可还包含(E)抗氧化剂作为有效改进耐热性的添加剂。抗氧化剂优选选自受阻酚化合物和受阻胺化合物。
虽然没有特别限制本文使用的受阻酚化合物，但是以下列出的受阻酚化合物是优选的。
1,3,5-三甲基-2,4,6-三(3,5-二叔丁基-4-羟基苯甲基)苯(商品名：IRGANOX1330)、2,6-二叔丁基-4-甲基酚(商品名：Sumilizer BHT)、2,5-二叔丁基氢醌(商品名：Nocrac NS-7)、2,6-二叔丁基-4-乙基酚(商品名：Nocrac M-17)、2,5-二叔戊基氢醌(商品名：Nocrac DAH)、2,2'-亚甲基双(4-甲基-6-叔丁基酚)(商品名：Nocrac NS-6)、3,5-二叔丁基-4-羟基苯甲基膦酸二乙酯(商品名：IRGANOX 1222)、4,4'-硫代双(3-甲基-6-叔丁基酚)(商品名：Nocrac 300)、2,2'-亚甲基双(4-乙基-6-叔丁基酚)(商品名：Nocrac NS-5)、4,4'-亚丁基双(3-甲基-6-叔丁基酚)(商品名：Adeka Stab AO-40)、2-叔丁基-6-(3-叔丁基-2-羟基-5-甲基苯甲基)-4-甲基苯基丙烯酸酯(商品名：Sumilizer GM)、2-[1-(2-羟基-3,5-二叔戊基苯基)乙基]-4,6-二叔戊基苯基丙烯酸酯(商品名：Sumilizer GS)、2,2'-亚甲基双[4-甲基-6-(α-甲基环己基)酚]、4,4'-亚甲基双(2,6-二叔丁基酚)(商品名：Seenox226M)、4,6-双(辛基硫代甲基)-邻-甲酚(商品名：IRGANOX1520L)、2,2'-亚乙基双(4,6-二叔丁基酚)、十八烷基3-(3,5-二叔丁基-4-羟基苯基)丙酸酯(商品名：IRGANOX 1076)、1,1,3-三(2-甲基-4-羟基-5-叔丁基苯基)丁烷(商品名：Adeka Stab AO-30)、四[亚甲基-(3,5-二叔丁基-4-羟基氢肉桂酸酯)]甲烷(商品名：Adeka Stab AO-60)、三亚乙基二醇双[3-(3-叔丁基-5-甲基-4-羟基苯基)丙酸酯](商品名：IRGANOX 245)、2,4-双(正辛基硫代)-6-(4-羟基-3,5-二叔丁基苯胺基)-1,3,5-三嗪(商品名：IRGANOX 565)、N,N'-六亚甲基双(3,5-二叔丁基-4-羟基氢肉桂酰胺)(商品名：IRGANOX1098)、1,6-己二醇-双[3-(3,5-二叔丁基-4-羟基苯基)丙酸酯](商品名：IRGANOX 259)、2,2-硫代-二亚乙基双[3-(3,5-二叔丁基-4-羟基苯基)丙酸酯](商品名：IRGANOX 1035)、3,9-双[2-[3-(3-叔丁基-4-羟基-5-甲基苯基)丙酰氧基]-1,1-二甲基乙基]2,4,8,10-四氧杂螺[5.5]十一烷(商品名：Sumilizer GA-80)、三(3,5-二叔丁基-4-羟基苯甲基)异氰脲酸酯(商品名：IRGANOX 3114)、双(乙基3,5-二叔丁基-4-羟基苯甲基膦酸酯)钙/聚乙烯蜡50/50混合物(商品名：IRGANOX 1425WL)、异辛基3-(3,5-二叔丁基-4-羟基苯基)丙酸酯(商品名：IRGANOX 1135)、4,4'-硫代双(6-叔丁基-3-甲基酚)(商品名：Sumilizer WX-R)、6-[3-(3-叔丁基-4-羟基-5-甲基苯基)丙氧基]-2,4,8,10-四叔丁基二苯并[d,f][1,3,2]二氧杂磷杂环己烷(dioxaphosphepin)(商品名：Sumilizer GP)等。
虽然没有特别限制本文使用的受阻胺化合物，但是以下列出的受阻胺化合物是优选的。
p,p'-二辛基二苯胺(商品名：IRGANOX 5057)、苯基-α-萘胺(商品名：Nocrac PA)、聚(2,2,4-三甲基-1,2-二氢喹啉)(商品名：Nocrac224、224-S)、6-乙氧基-2,2,4-三甲基-1,2-二氢喹啉(商品名：Nocrac AW)、N,N'-二苯基-对苯二胺(商品名：Nocrac DP)、N,N'-二-β-萘基-对苯二胺(商品名：Nocrac White)、N-苯基-N'-异丙基-对苯二胺(商品名：Nocrac 810NA)、N,N'-二烯丙基-对苯二胺(商品名：Nonflex TP)、4,4'-(α,α-二甲基苯甲基)二苯胺(商品名：Nocrac CD)、p,p-甲苯磺酰胺二苯胺(商品名：Nocrac TD)、N-苯基-N'-(3-甲基丙烯酰氧-2-羟基丙基)-对苯二胺(商品名：Nocrac G1)、N-(1-甲基庚基)-N'-苯基-对苯二胺(商品名：Ozonon 35)、N,N'-二-仲丁基-对苯二胺(商品名：Sumilizer BPA)、N-苯基-N'-1,3-二甲基丁基-对苯二胺(商品名：Antigene 6C)、烷基化的二苯胺(商品名：Sumilizer9A)、二甲基-1-(2-羟基乙基)-4-羟基-2,2,6,6-四甲基哌啶琥珀酸酯缩聚物(商品名:Tinuvin 622LD)、聚[[6-(1,1,3,3-四甲基丁基)氨基]-1,3,5-三嗪-2,4-二基][(2,2,6,6-四甲基-4-哌啶基)亚胺基]六亚甲基[(2,2,6,6-四甲基-4-哌啶基)亚胺基]](商品名：CHIMASSORB944)、N,N'-双(3-氨基丙基)乙二胺-2,4-双[N-丁基-N-(1,2,2,6,6-五甲基-4-哌啶基)氨基]-6-氯-1,3,5-三嗪缩合物(商品名：CHIMASSORB 119FL)、双(1-辛氧基-2,2,6,6-四甲基-4-哌啶基)癸二酸酯(商品名:Tinuvin 123)、双(2,2,6,6-四甲基-4-哌啶基)癸二酸酯(商品名:Tinuvin 770)、双(1,2,2,6,6-五甲基-4-哌啶基)2-(3,5-二叔丁基-4-羟基苯甲基)-2-正丁基丙二酸酯(商品名：Tinuvin 144)、双(1,2,2,6,6-五甲基-4-哌啶基)癸二酸酯(商品名:Tinuvin 765)、四(1,2,2,6,6-五甲基-4-哌啶基)1,2,3,4-丁烷四羧酸酯(商品名:LA-57)、四(2,2,6,6-四甲基-4-哌啶基)1,2,3,4-丁烷四羧酸酯(商品名:LA-52)、1,2,3,4-丁烷四羧酸与1,2,2,6,6-五甲基-4-哌啶醇和1-十三醇的酯化混合物(商品名：LA-62)、1,2,3,4-丁烷四羧酸与2,2,6,6-四甲基-4-哌啶醇和1-十三醇的酯化混合物(商品名：LA-67)、1,2,3,4-丁烷四羧酸与1,2,2,6,6-五甲基-4-哌啶醇和3,9-双(2-羟基-1,1-二甲基乙基)-2,4,8,10-四氧杂螺[5.5]十一烷的酯化混合物(商品名：LA-63P)、1,2,3,4-丁烷四羧酸与2,2,6,6-四甲基-4-哌啶醇和3,9-双(2-羟基-1,1-二甲基乙基)-2,4,8,10-四氧杂螺[5.5]十一烷的酯化混合物(商品名：LA-68LD)、(2,2,6,6-四亚甲基-4-哌啶基)-2-亚丙基羧酸酯(商品名:Adeka Stab LA-82)、(1,2,2,6,6-五甲基-4-哌啶基)-2-亚丙基羧酸酯(商品名:Adeka Stab LA-87)等。
没有特别限制使用的组分(E)的量，只要没有损害本发明的益处。当使用时，组分(E)的量优选为树脂组合物的0.01至1重量％。可单独地或以混合物使用抗氧化剂。
其它添加剂
除前述组分之外，感光性树脂组合物可含有任选的添加剂，例如常使用于改进涂层性质的表面活性剂和硅烷偶联剂。
优选的表面活性剂是非离子性表面活性剂例如含氟化合物表面活性剂例如全氟烷基聚氧乙烯乙醇、氟化的烷基酯、全氟烷基氧化胺和氟化的有机硅氧烷化合物。这些表面活性剂是可商购得到的。说明性的实例包括来自3M的
FC-430，来自AGC SeimiChemical Co.,Ltd.的
S-141和S-145，来自Daikin Industries Ltd.的
DS-401、DS-4031和DS-451，来自DIC Corp.的
F-8151和来自Shin-Etsu Chemical Co.,Ltd.的X-70-093。优选的表面活性剂是Fluorad FC-430和X-70-093。没有特别限制表面活性剂的量，只要没有损害本发明的益处。当使用时，表面活性剂的量优选为树脂组合物的0.01至1重量％。
硅烷偶联剂的引入对于增强树脂组合物对被粘物的粘合性是有效的。适合的硅烷偶联剂包括环氧硅烷偶联剂和芳香氨基硅烷偶联剂。可单独地或以混合物使用硅烷偶联剂。没有特别限制硅烷偶联剂的使用量，只要没有损害本发明的益处。当使用时，硅烷偶联剂的量优选为树脂组合物的0.01至5重量％。
采用任何期望的方式制备本发明的感光性树脂组合物。例如，可通过搅拌和混合前述组分并任选地使混合物通过过滤器以去除任何固体来制备。
图案形成方法
本发明的另一实施方案是使用以上限定的感光性树脂组合物的图案形成方法，该方法包括以下步骤：
(i)应用感光性树脂组合物至基板上以在其上形成感光性树脂膜，
(ii)使感光性树脂膜暴露于辐照，和
(iii)用显影剂使曝光的树脂膜显影，由此形成细微尺寸图案。
在步骤(i)中，应用感光性树脂组合物至基板上以在其上形成感光性树脂膜。基板的实例包括硅晶片、玻璃晶片、石英晶片、塑料电路基板和陶瓷电路基板。
可通过任何公知的技术形成感光性树脂膜。例如，通过涂覆技术例如浸渍、旋涂或辊涂将感光性树脂组合物涂覆至基板上。可对于特定目的适当选择涂层重量，优选从而形成具有0.1至100μm厚度的树脂膜。
在这一点，如果需要，为了有效的光固化反应，可预烘焙涂层以蒸发掉溶剂等。例如可在40至160℃下进行预烘焙1分钟至约1小时。
接下来在步骤(ii)中，使感光性树脂膜暴露于辐照。曝光辐照优选具有240至500nm的波长。辐照的实例包括来自辐照发射单元的各种波长的辐照，特别是UV辐照例如g-或i-线和深UV(248nm)。适当的曝光计量是10至5,000mJ/cm2。
可通过光掩模进行曝光。本文使用的光掩模可为例如穿孔有期望图案的光掩膜。虽然没有特别限制光掩模的材料，但是能够屏蔽波长240至500nm的辐照的材料是优选的，例如铬。
下一个步骤可为曝光后烘焙(PEB)，其有效的增强显影敏感性。例如在40至160℃下进行PEB持续5至30分钟。
曝光或PEB之后的步骤(iii)是在显影剂中显影树脂膜。优选的显影剂是有机溶剂例如异丙醇(IPA)、丙二醇单甲基醚(PGME)和丙二醇单甲基醚乙酸酯(PGMEA)。通过在基于有机溶剂的显影剂中显影，树脂膜的未曝光区域被溶解掉，从而产生负图案。显影以常规方式实现，例如通过将曝光的膜浸入显影剂中。如果需要，显影之后是冲洗、漂洗和干燥。以这种方式，获得了具有期望图案的树脂膜。
虽然描述了图案形成方法，但是有时不需要形成图案。当简单地期望形成均匀的膜时，例如可按照与以上相同的方法，除了在步骤(ii)中将树脂膜直接暴露于具有适合波长的辐照，即不需要光掩模。
在随后的步骤(iv)中，如果需要，可在优选120至300℃的温度下的烘箱或加热板中后固化图案化的膜10分钟至10小时用于提高树脂膜的交联密度并去除任何残余的挥发性物质。
光半导体器件
可通过使用感光性树脂组合物并且根据前述方法将其加工以形成细微尺寸图案来制备光半导体器件。因为感光性树脂组合物的膜具有优异的透明性、耐光性和耐热性，所以具有该膜的光半导体器件被有利地用作光学器件，包括发光器件例如LED、光接收器件例如光电二极管、光学传感器和CMOS图像传感器、和光学透过器件例如光波导。优选地，膜相对于405nm波长的光而言具有至少92％、更优选至少96％、甚至更优选至少98％的透过率。
实施例
以下通过说明的方式而非通过限制的方式给出本发明的实施例。特别地，通过GPC在以下条件下相对于单分散性聚苯乙烯标准物测量重均分子量(Mw)，条件包括柱TSKgelSuper HZM-H(Tosoh Corp.)、流速0.6mL/min、洗脱液THF和柱温度40℃。使用Bruker Corp.的分析仪用于1H-NMR光谱学。所有份以重量计(pbw)。
以下确认在实施例和比较例中使用的化合物(S-1)、(S-2a)、(S-2b)、(S-3a)、(S-3b)、(S-4)、(S-5)和(S-6)。
[1]聚合物的合成和评价
(1)聚合物的合成
实施例1-1
合成聚合物1
使用26.5g(0.10mol)的化合物(S-4)和108.9g(0.90mol)的化合物(S-3a)、然后使用2,000g的甲苯装入配备有搅拌器、温度计、氮吹扫管线和回流冷凝器的10-L烧瓶，并在70℃下加热。此后，添加1.0g的氯铂酸甲苯溶液(Pt浓度0.5重量％)，并且在1小时中滴加184.3g(0.95mol)的化合物(S-1)和9.3g(0.05mol)的化合物(S-2b)(以摩尔比计总的氢甲硅烷基/总的碳-碳双键＝1/1)。在完成滴加之后，在100℃下加热溶液并老化6小时。在真空中从反应溶液蒸馏掉甲苯，从而产生聚合物1。聚合物1具有15,000的Mw和19.9重量％的硅氧烷单元含量。在1H-NMR分析中，发现聚合物1由重复单元(A1)至(A4)构成。
实施例1-2
合成聚合物2
使用238.5g(0.90mol)的化合物(S-4)和12.1g(0.10mol)的化合物(S-3a)、然后使用2,000g的甲苯装入配备有搅拌器、温度计、氮吹扫管线和回流冷凝器的10-L烧瓶，并在70℃下加热。此后，添加1.0g的氯铂酸甲苯溶液(Pt浓度0.5重量％)，并且在1小时中滴加184.3g(0.95mol)的化合物(S-1)和79.3g(0.05mol)的化合物(S-2b)(以摩尔比计总的氢甲硅烷基/总的碳-碳双键＝1/1)。在完成滴加之后，在100℃下加热溶液并老化6小时。在真空中从反应溶液蒸馏掉甲苯，从而产生聚合物2。聚合物2具有7,000的Mw和15.4重量％的硅氧烷单元含量。在1H-NMR分析中，发现聚合物2由重复单元(A1)至(A4)构成。
实施例1-3
合成聚合物3
使用132.5g(0.50mol)的化合物(S-4)和60.5g(0.50mol)的化合物(S-3a)、然后使用2,000g的甲苯装入配备有搅拌器、温度计、氮吹扫管线和回流冷凝器的10-L烧瓶，并在70℃下加热。此后，添加1.0g的氯铂酸甲苯溶液(Pt浓度0.5重量％)，并且在1小时中滴加38.8g(0.20mol)的化合物(S-1)和1268.0g(0.80mol)的化合物(S-2b)(以摩尔比计总的氢甲硅烷基/总的碳-碳双键＝1/1)。在完成滴加之后，在100℃下加热溶液并老化6小时。在真空中从反应溶液蒸馏掉甲苯，从而产生聚合物3。聚合物3具有180,000的Mw和84.5重量％的硅氧烷单元含量。在1H-NMR分析中，发现聚合物3由重复单元(A1)至(A4)构成。
实施例1-4
合成聚合物4
使用159.0g(0.60mol)的化合物(S-4)和48.4g(0.40mol)的化合物(S-3a)、然后使用2,000g的甲苯装入配备有搅拌器、温度计、氮吹扫管线和回流冷凝器的10-L烧瓶，并在70℃下加热。此后，添加1.0g的氯铂酸甲苯溶液(Pt浓度0.5重量％)，并且在1小时中滴加155.2g(0.80mol)的化合物(S-1)和604.0g(0.20mol)的化合物(S-2a)(以摩尔比计总的氢甲硅烷基/总的碳-碳双键＝1/1)。在完成滴加之后，在100℃下加热溶液并老化6小时。在真空中从反应溶液蒸馏掉甲苯，从而产生聚合物4。聚合物4具有100,000的Mw和62.5重量％的硅氧烷单元含量。在1H-NMR分析中，发现聚合物4由重复单元(A1)至(A4)构成。
实施例1-5
合成聚合物5
使用79.5g(0.30mol)的化合物(S-4)和84.7g(0.70mol)的化合物(S-3a)、然后使用2,000g的甲苯装入配备有搅拌器、温度计、氮吹扫管线和回流冷凝器的10-L烧瓶，并在70℃下加热。此后，添加1.0g的氯铂酸甲苯溶液(Pt浓度0.5重量％)，并且在1小时中滴加174.6g(0.90mol)的化合物(S-1)和302.0g(0.10mol)的化合物(S-2a)(以摩尔比计总的氢甲硅烷基/总的碳-碳双键＝1/1)。在完成滴加之后，在100℃下加热溶液并老化6小时。在真空中从反应溶液蒸馏掉甲苯，从而产生聚合物5。聚合物5具有60,000的Mw和47.1重量％的硅氧烷单元含量。在1H-NMR分析中，发现聚合物5由重复单元(A1)至(A4)构成。
实施例1-6
合成聚合物6
使用132.5g(0.50mol)的化合物(S-4)和60.5g(0.50mol)的化合物(S-3a)、然后使用2,000g的甲苯装入配备有搅拌器、温度计、氮吹扫管线和回流冷凝器的10-L烧瓶，并在70℃下加热。此后，添加1.0g的氯铂酸甲苯溶液(Pt浓度0.5重量％)，并且在1小时中滴加174.6g(0.90mol)的化合物(S-1)和302.0g(0.10mol)的化合物(S-2a)(以摩尔比计总的氢甲硅烷基/总的碳-碳双键＝1/1)。在完成滴加之后，在100℃下加热溶液并老化6小时。在真空中从反应溶液蒸馏掉甲苯，从而产生聚合物6。聚合物6具有40,000的Mw和45.1重量％的硅氧烷单元含量。在1H-NMR分析中，发现聚合物6由重复单元(A1)至(A4)构成。
实施例1-7
合成聚合物7
使用238.5g(0.90mol)的化合物(S-4)和16.2g(0.10mol)的化合物(S-3b)、然后使用2,000g的甲苯装入配备有搅拌器、温度计、氮吹扫管线和回流冷凝器的10-L烧瓶，并在70℃下加热。此后，添加1.0g的氯铂酸甲苯溶液(Pt浓度0.5重量％)，并且在1小时中滴加184.3g(0.95mol)的化合物(S-1)和79.3g(0.05mol)的化合物(S-2b)(以摩尔比计总的氢甲硅烷基/总的碳-碳双键＝1/1)。在完成滴加之后，在100℃下加热溶液并老化6小时。在真空中从反应溶液蒸馏掉甲苯，从而产生聚合物7。聚合物7具有7,000的Mw和15.3重量％的硅氧烷单元含量。在1H-NMR分析中，发现聚合物7由重复单元(A1)至(A4)构成。
实施例1-8
合成聚合物8
使用159.0g(0.60mol)的化合物(S-4)和64.8g(0.40mol)的化合物(S-3b)、然后使用2,000g的甲苯装入配备有搅拌器、温度计、氮吹扫管线和回流冷凝器的10-L烧瓶，并在70℃下加热。此后，添加1.0g的氯铂酸甲苯溶液(Pt浓度0.5重量％)，并且在1小时中滴加155.2g(0.80mol)的化合物(S-1)和604.0g(0.20mol)的化合物(S-2a)(以摩尔比计总的氢甲硅烷基/总的碳-碳双键＝1/1)。在完成滴加之后，在100℃下加热溶液并老化6小时。在真空中从反应溶液蒸馏掉甲苯，从而产生聚合物8。聚合物8具有100,000的Mw和61.4重量％的硅氧烷单元含量。在1H-NMR分析中，发现聚合物8由重复单元(A1)至(A4)构成。
比较例1-1
合成比较聚合物1
使用212.0g(0.80mol)的化合物(S-4)和86.0g(0.20mol)的化合物(S-6)、然后使用2,000g的甲苯装入配备有搅拌器、温度计、氮吹扫管线和回流冷凝器的10-L烧瓶，并在70℃下加热。此后，添加1.0g的氯铂酸甲苯溶液(Pt浓度0.5重量％)，并且在1小时中滴加184.3g(0.95mol)的化合物(S-1)和79.3g(0.05mol)的化合物(S-2b)(以摩尔比计总的氢甲硅烷基/总的碳-碳双键＝1/1)。在完成滴加之后，在100℃下加热溶液并老化6小时。在真空中从反应溶液蒸馏掉甲苯，从而产生比较聚合物1。比较聚合物1具有8,000的Mw和14.1重量％的硅氧烷单元含量。
比较例1-2
合成比较聚合物2
使用212.0g(0.80mol)的化合物(S-4)和78.4g(0.20mol)的化合物(S-5)、然后使用2,000g的甲苯装入配备有搅拌器、温度计、氮吹扫管线和回流冷凝器的10-L烧瓶，并在70℃下加热。此后，添加1.0g的氯铂酸甲苯溶液(Pt浓度0.5重量％)，并且在1小时中滴加38.8g(0.20mol)的化合物(S-1)和1268.0g(0.80mol)的化合物(S-2b)(以摩尔比计总的氢甲硅烷基/总的碳-碳双键＝1/1)。在完成滴加之后，在100℃下加热溶液并老化6小时。在真空中从反应溶液蒸馏掉甲苯，从而产生比较聚合物2。比较聚合物2具有85,000的Mw和79.4重量％的硅氧烷单元含量。
比较例1-3
合成比较聚合物3
使用96.8g(0.80mol)的化合物(S-3a)和86.0g(0.20mol)的化合物(S-6)、然后使用2,000g的甲苯装入配备有搅拌器、温度计、氮吹扫管线和回流冷凝器的10-L烧瓶，并在70℃下加热。此后，添加1.0g的氯铂酸甲苯溶液(Pt浓度0.5重量％)，并且在1小时中滴加174.6g(0.90mol)的化合物(S-1)和158.5g(0.10mol)的化合物(S-2b)(以摩尔比计总的氢甲硅烷基/总的碳-碳双键＝1/1)。在完成滴加之后，在100℃下加热溶液并老化6小时。在真空中从反应溶液蒸馏掉甲苯，从而产生比较聚合物3。比较聚合物3具有21,000的Mw和30.7重量％的硅氧烷单元含量。
比较例1-4
合成比较聚合物4
使用96.8g(0.80mol)的化合物(S-3a)和78.4g(0.20mol)的化合物(S-5)、然后使用2,000g的甲苯装入配备有搅拌器、温度计、氮吹扫管线和回流冷凝器的10-L烧瓶，并在70℃下加热。此后，添加1.0g的氯铂酸甲苯溶液(Pt浓度0.5重量％)，并且在1小时中滴加174.6g(0.90mol)的化合物(S-1)和302.0g(0.10mol)的化合物(S-2a)(以摩尔比计总的氢甲硅烷基/总的碳-碳双键＝1/1)。在完成滴加之后，在100℃下加热溶液并老化6小时。在真空中从反应溶液蒸馏掉甲苯，从而产生比较聚合物4。比较聚合物4具有53,000的Mw和46.3重量％的硅氧烷单元含量。
比较例1-5
合成比较聚合物5
使用215.0g(0.50mol)的化合物(S-6)和196.0g(0.50mol)的化合物(S-5)、然后使用2,000g的甲苯装入配备有搅拌器、温度计、氮吹扫管线和回流冷凝器的10-L烧瓶，并在70℃下加热。此后，添加1.0g的氯铂酸甲苯溶液(Pt浓度0.5重量％)，并且在1小时中滴加135.8g(0.70mol)的化合物(S-1)和906.0g(0.30mol)的化合物(S-2a)(以摩尔比计总的氢甲硅烷基/总的碳-碳双键＝1/1)。在完成滴加之后，在100℃下加热溶液并老化6小时。在真空中从反应溶液蒸馏掉甲苯，从而产生比较聚合物5。比较聚合物5具有93,000的Mw和62.4重量％的硅氧烷单元含量。
比较例1-6
合成比较聚合物6
使用430.0g(1.00mol)的化合物(S-6)、然后使用2,000g的甲苯装入配备有搅拌器、温度计、氮吹扫管线和回流冷凝器的10-L烧瓶，并在70℃下加热。此后，添加1.0g的氯铂酸甲苯溶液(Pt浓度0.5重量％)，并且在1小时中滴加155.2g(0.80mol)的化合物(S-1)和604.0g(0.20mol)的化合物(S-2a)(以摩尔比计总的氢甲硅烷基/总的碳-碳双键＝1/1)。在完成滴加之后，在100℃下加热溶液并老化6小时。在真空中从反应溶液蒸馏掉甲苯，从而产生比较聚合物6。比较聚合物6具有67,000的Mw和50.8重量％的硅氧烷单元含量。
比较例1-7
合成比较聚合物7
使用392.0g(1.00mol)的化合物(S-5)、然后使用2,000g的甲苯装入配备有搅拌器、温度计、氮吹扫管线和回流冷凝器的10-L烧瓶，并在70℃下加热。此后，添加1.0g的氯铂酸甲苯溶液(Pt浓度0.5重量％)，并且在1小时中滴加155.2g(0.80mol)的化合物(S-1)和604.0g(0.20mol)的化合物(S-2a)(以摩尔比计总的氢甲硅烷基/总的碳-碳双键＝1/1)。在完成滴加之后，在100℃下加热溶液并老化6小时。在真空中从反应溶液蒸馏掉甲苯，从而产生比较聚合物7。比较聚合物7具有100,000的Mw和52.5重量％的硅氧烷单元含量。
比较例1-8
合成比较聚合物8
使用265.0g(1.00mol)的化合物(S-4)、然后使用2,000g的甲苯装入配备有搅拌器、温度计、氮吹扫管线和回流冷凝器的10-L烧瓶，并在70℃下加热。此后，添加1.0g的氯铂酸甲苯溶液(Pt浓度0.5重量％)，并且在1小时中滴加155.2g(0.80mol)的化合物(S-1)和604.0g(0.20mol)的化合物(S-2a)(以摩尔比计总的氢甲硅烷基/总的碳-碳双键＝1/1)。在完成滴加之后，在100℃下加热溶液并老化6小时。在真空中从反应溶液蒸馏掉甲苯，从而产生比较聚合物8。比较聚合物8具有70,000的Mw和59.0重量％的硅氧烷单元含量。
(2)光透过率测试
实施例2-1至2-8
通过将聚合物1至8中每个以50重量％的浓度溶解在环戊酮中来制备树脂溶液。将树脂溶液涂覆至玻璃晶片上并在60℃下烘焙30分钟并在氮气氛中190℃下烘焙2小时，从而形成10μm厚的树脂膜。使用分光光度计U-3900H(Hitachi High-Tech Science Corp.)，相对于405nm波长的光测量膜的透过率。结果示于表1中。
表1
在50℃下的烘箱中，用波长405nm和功率1W的激光辐照连续照射样品(如以上在玻璃晶片上具有树脂膜)。测定在激光照射100小时和1,000小时之后的光透过率值。结果示于表2中。
表2
聚合物1至8表面能够合成在它们的主链中含有聚硅氧烷、硅亚苯基、异氰脲酸和降冰片烯骨架并在它们的侧链中具有环氧基团的新的聚合物。聚合物的膜具有高透明性和耐光性。
[2]感光性树脂组合物的制备和评价
实施例3-1至3-10和比较例2-1至2-19
(1)制备感光性树脂组合物
通过以下制备感光性树脂组合物：按照表3至5中所示配方组合聚合物1、3、5至8或比较聚合物1至8作为组分(A)，光致产酸剂B-1或B-2作为组分(B)，交联剂C-1、C-2或C-3作为组分(C)、环戊酮(CP)作为溶剂(D)和抗氧化剂E-1或E-2作为组分(E)，搅拌它们直至溶解并通过具有0.2μm孔径的
过滤器精细过滤。
表3
表4
表5
以下确认光致产酸剂B-1和B-2，交联剂C-1至C-3，抗氧化剂E-1和E-2。
光致产酸剂B-1
光致产酸剂B-2：San-Apro Ltd.的CPI-210S
交联剂C-1、C-2、C-3
抗氧化剂E-1：Chimassorb 119FL(BASF)
抗氧化剂E-2：Irganox 3114(BASF)
(2)评价图案形成
使用旋涂机，将每种感光性树脂组合物涂覆至8-英寸硅晶片(其已用六甲基二硅氮烷(HMDS)底涂)上，从而形成10μm厚的膜。将涂覆的晶片放置在热板上并在110℃下加热干燥3分钟以便从组合物去除溶剂。使用接触对准器型曝光系统，通过适合于形成线和间隔(line-and-space)图案和接触孔图案的掩模将感光性树脂膜暴露于365nm的辐照。在120℃下的热板上曝光后烘焙(PEB)树脂膜3分钟并然后冷却。通过喷涂PGMEA持续300秒使树脂膜显影，从而形成图案。
在烘箱中使晶片上的感光性树脂膜(如以上进行了图案化)后固化，该烘箱中在190℃下加热膜2小时同时用氮吹扫烘箱。在扫描电子显微镜(SEM)下，观察50μm、30μm、20μm、10μm和5μm的产生的接触孔图案横截面。将孔穿透膜至底部的最小孔图案报告为最大分辨率。根据横截面照片，评价50μm的接触孔图案的垂直度。如下评定树脂膜：垂直轮廓为“优异”，稍微倒锥形轮廓为“好”，倒锥形轮廓为“一般”，和开口不良为“NG”。结果示于表6至8中。
表6
表7
表8
(3)光透过率测试1
使用旋涂机，将每种感光性树脂组合物涂覆至8-英寸玻璃晶片上从而形成20μm厚的树脂膜。将涂覆的晶片放置在热板上并在110℃下加热干燥3分钟以便从组合物去除溶剂。
使用Mask Aligner MA8(SUSS MicroTec AG)，将玻璃晶片上的膜在其整个表面上直接暴露于来自高压汞灯的360nm波长的光，即不通过掩模(全面曝光)。将膜PEB并浸渍在PGMEA中。然后在190℃下的烘箱中加热在这些操作之后残余的膜2小时，从而产生固化膜。使用分光光度计U-3900H(Hitachi High-Tech Science Corp.)，用405nm波长的光测量固化膜的透过率。结果示于表9至11中。
表9
表10
表11
(4)光透过率测试2
在150℃下的烘箱中，用波长405nm和功率1W的激光辐照连续照射样品(如在(3)光透过率测试1中所制备，在玻璃晶片上的树脂膜的形式)。测定了在405nm下激光照射2,000小时之后透过率改变，假设初始透过率为100％。结果示于表12至14中。
表12
表13
表14
(5)可靠性评价(粘合性和抗裂性)
通过以40,000rpm的转轴转速和20mm/sec的切断速度操作带有切割刀片的切割锯(DISCO Corp.的DAD685)，如在(3)光透过率测试1中制备的带有感光性树脂膜的晶片被切割成10mm×10mm的方块件(测试样品)。十个测试样品(对于每个实施例)经受如下热循环测试：重复2,000循环的在-25℃下保持10分钟并在125℃下保持10分钟。在热循环测试之后，检查树脂膜是否从晶片剥离和树脂膜是否开裂。如下评定样品组：当没有样品剥离或开裂时为“OK”；当一个或多个样品剥离时为“剥离”；和当一个或多个样品开裂时为“开裂”。结果示于表15至17中。
表15
表16
表17
(6)耐热性测试
通过将每种感光性树脂组合物旋涂至硅晶片上、全面曝光和PEB来制备硅晶片样品。测量测试之前样品的重量。样品保持在150℃下的烘箱中2,000小时，此后取出样品并测量重量。将测试前后的重量改变计算为耐热性指标。如下评定样品：当测试之后的重量改变小于0.5重量％时为“好”并且当重量改变等于或大于0.5重量％时为“差”。结果示于表18至20中。
表18
表19
表20
从结果显而易见，在本发明范围内的感光性树脂组合物形成膜(或涂层)，可将该膜(或涂层)加工成细微尺寸图案，表明作为感光性材料的令人满意的性质。另外，膜具有高的光透过率、令人满意的耐光性、可靠性(粘合性、抗裂性)和耐热性并因此可用作光半导体器件的材料。
日本专利申请号2018-218755和2019-084911通过引用并入本文。
虽然已经描述了一些优选实施方案，但是鉴于以上教导可对其进行许多修改和变化。因此应理解可在不脱离所附权利要求的范围的情况下，以不同于具体描述的方式实施本发明。
Claims (13)
1.聚合物，其在主链中包含聚硅氧烷骨架、硅亚苯基骨架、异氰脲酸骨架和降冰片烯骨架并在侧链中具有环氧基团，
其中，其包含具有以下式(A1)至(A4)的重复单元：
其中R1至R4各自独立地为C1-C20一价烃基，其可含有杂原子，m各自独立地为1至600的整数，条件是当m是至少2的整数时，基团R3可为相同的或不同的并且基团R4可为相同的或不同的，a1、a2、a3和a4是在以下范围的数：0<a1<1、0<a2<1、0<a3<1、0<a4<1，和a1+a2+a3+a4＝1，
X1是具有式(X1)的二价基团：
其中R11和R12各自独立地为氢或甲基，n1和n2各自独立地为0至7的整数，R13是C1-C8二价烃基，其中碳原子之间可插入酯键或醚键，和
X2是具有式(X2)的二价基团：
其中R21和R22各自独立地为氢或C1-C20烷基基团，其可含有杂原子，并且k是0至10的整数。
2.根据权利要求1所述的聚合物，其中具有10μm厚度的聚合物的膜相对于405nm波长的光而言具有至少95％的透过率。
3.根据权利要求1所述的聚合物，其中m是8至100的整数。
4.根据权利要求1所述的聚合物，其中R21和R22是氢。
5.根据权利要求1所述的聚合物，其中k是0。
6.根据权利要求1所述的聚合物，其具有3,000至500,000的重均分子量。
7.感光性树脂组合物，其包含(A)权利要求1的聚合物和(B)光致产酸剂。
8.根据权利要求7所述的感光性树脂组合物，其中组分(B)以每100重量份的组分(A)0.05至20重量份的量存在。
9.根据权利要求7所述的感光性树脂组合物，其还包含(C)阳离子聚合性交联剂。
10.根据权利要求7所述的感光性树脂组合物，其还包含(D)溶剂。
11.根据权利要求7所述的感光性树脂组合物，其还包含(E)抗氧化剂。
12.图案形成方法，包括以下步骤：
(i)应用权利要求7的感光性树脂组合物至基板上以在其上形成感光性树脂膜，
(ii)使该感光性树脂膜暴露于辐照，和
(iii)用显影剂使曝光的树脂膜显影。
13.光半导体器件的制造方法，包括权利要求12的图案形成方法，该器件包含图案化的感光性树脂膜。
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