JPWO2018003470A1 - スルホニウム塩、光酸発生剤、光硬化性組成物、及びその硬化体 - Google Patents
スルホニウム塩、光酸発生剤、光硬化性組成物、及びその硬化体 Download PDFInfo
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- JPWO2018003470A1 JPWO2018003470A1 JP2018525019A JP2018525019A JPWO2018003470A1 JP WO2018003470 A1 JPWO2018003470 A1 JP WO2018003470A1 JP 2018525019 A JP2018525019 A JP 2018525019A JP 2018525019 A JP2018525019 A JP 2018525019A JP WO2018003470 A1 JPWO2018003470 A1 JP WO2018003470A1
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- Prior art keywords
- group
- parts
- phenyl
- sulfonium salt
- general formula
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 119
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 title claims abstract description 32
- -1 tetrakis (pentafluorophenyl) borate salt Chemical class 0.000 claims abstract description 168
- 150000001875 compounds Chemical class 0.000 claims abstract description 34
- 125000004432 carbon atom Chemical group C* 0.000 claims description 40
- 125000003118 aryl group Chemical group 0.000 claims description 35
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 19
- 125000004104 aryloxy group Chemical group 0.000 claims description 19
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 125000004423 acyloxy group Chemical group 0.000 claims description 14
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 14
- 125000004414 alkyl thio group Chemical group 0.000 claims description 14
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 13
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 13
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 13
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 13
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 13
- 125000005110 aryl thio group Chemical group 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 13
- 125000003277 amino group Chemical group 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 9
- 229920001774 Perfluoroether Chemical group 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 3
- 239000002253 acid Substances 0.000 abstract description 21
- 238000006243 chemical reaction Methods 0.000 abstract description 20
- 229920005989 resin Polymers 0.000 abstract description 19
- 239000011347 resin Substances 0.000 abstract description 19
- 238000010538 cationic polymerization reaction Methods 0.000 abstract description 18
- 229910052751 metal Inorganic materials 0.000 abstract description 18
- 239000002184 metal Substances 0.000 abstract description 18
- 238000012360 testing method Methods 0.000 abstract description 14
- 239000003505 polymerization initiator Substances 0.000 abstract description 10
- 230000007797 corrosion Effects 0.000 abstract description 9
- 238000005260 corrosion Methods 0.000 abstract description 9
- 238000004132 cross linking Methods 0.000 abstract description 9
- 231100000331 toxic Toxicity 0.000 abstract description 6
- 230000002588 toxic effect Effects 0.000 abstract description 6
- 230000006866 deterioration Effects 0.000 abstract description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 116
- 239000000047 product Substances 0.000 description 70
- 230000015572 biosynthetic process Effects 0.000 description 54
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 53
- 238000003786 synthesis reaction Methods 0.000 description 53
- 238000005160 1H NMR spectroscopy Methods 0.000 description 52
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 52
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 51
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 49
- 229910052744 lithium Inorganic materials 0.000 description 49
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 34
- 239000002904 solvent Substances 0.000 description 33
- 239000010410 layer Substances 0.000 description 32
- 238000002360 preparation method Methods 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- 239000000463 material Substances 0.000 description 27
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 25
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 20
- 239000000243 solution Substances 0.000 description 20
- 238000004519 manufacturing process Methods 0.000 description 19
- LLAVBEWIQQUQFR-UHFFFAOYSA-N 1-phenyl-4-phenylsulfanylbenzene Chemical group C=1C=C(C=2C=CC=CC=2)C=CC=1SC1=CC=CC=C1 LLAVBEWIQQUQFR-UHFFFAOYSA-N 0.000 description 18
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000003795 chemical substances by application Substances 0.000 description 17
- 230000003287 optical effect Effects 0.000 description 16
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
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- 238000001723 curing Methods 0.000 description 13
- 150000002500 ions Chemical class 0.000 description 13
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 12
- 238000004440 column chromatography Methods 0.000 description 11
- 239000003480 eluent Substances 0.000 description 11
- 238000004128 high performance liquid chromatography Methods 0.000 description 11
- 230000007935 neutral effect Effects 0.000 description 11
- 239000000758 substrate Substances 0.000 description 11
- 239000003963 antioxidant agent Substances 0.000 description 10
- 239000002216 antistatic agent Substances 0.000 description 10
- 239000002245 particle Substances 0.000 description 10
- MNTZJPDMAWZTNF-UHFFFAOYSA-N C[Si](C1=CC=C(C=C1)S(=O)C1=CC=CC=C1)(C)C Chemical compound C[Si](C1=CC=C(C=C1)S(=O)C1=CC=CC=C1)(C)C MNTZJPDMAWZTNF-UHFFFAOYSA-N 0.000 description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 9
- 239000011248 coating agent Substances 0.000 description 9
- 238000000576 coating method Methods 0.000 description 9
- 150000002430 hydrocarbons Chemical group 0.000 description 9
- 239000000049 pigment Substances 0.000 description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
- SJEIKLQGBGHSQR-UHFFFAOYSA-N C1(=CC=CC=C1)SC1=CC=C(C=C1)[Si](C)(C)C Chemical compound C1(=CC=CC=C1)SC1=CC=C(C=C1)[Si](C)(C)C SJEIKLQGBGHSQR-UHFFFAOYSA-N 0.000 description 8
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 8
- 229910018286 SbF 6 Inorganic materials 0.000 description 8
- 239000010949 copper Substances 0.000 description 8
- SFUNUNVTCWPJPU-UHFFFAOYSA-N 1-(benzenesulfinyl)-4-phenoxybenzene Chemical compound C=1C=C(OC=2C=CC=CC=2)C=CC=1S(=O)C1=CC=CC=C1 SFUNUNVTCWPJPU-UHFFFAOYSA-N 0.000 description 7
- DGZWSSPZYYPSAS-UHFFFAOYSA-N 1-(benzenesulfinyl)-4-phenylbenzene Chemical group C=1C=C(C=2C=CC=CC=2)C=CC=1S(=O)C1=CC=CC=C1 DGZWSSPZYYPSAS-UHFFFAOYSA-N 0.000 description 7
- 0 C=*c(cccc1)c1S(c(cc1)ccc1[Si](c1ccccc1)(c1ccccc1)c1ccccc1)c(cc1*=C)ccc1Sc(cc1)ccc1[Si](c1ccccc1)(c1ccccc1)c1ccccc1 Chemical compound C=*c(cccc1)c1S(c(cc1)ccc1[Si](c1ccccc1)(c1ccccc1)c1ccccc1)c(cc1*=C)ccc1Sc(cc1)ccc1[Si](c1ccccc1)(c1ccccc1)c1ccccc1 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000000853 adhesive Substances 0.000 description 7
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 239000003063 flame retardant Substances 0.000 description 7
- 239000007870 radical polymerization initiator Substances 0.000 description 7
- QSWFKGKKOXAKBE-UHFFFAOYSA-N 1-phenoxy-4-phenylsulfanylbenzene Chemical compound C=1C=C(SC=2C=CC=CC=2)C=CC=1OC1=CC=CC=C1 QSWFKGKKOXAKBE-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 230000001070 adhesive effect Effects 0.000 description 6
- 235000010290 biphenyl Nutrition 0.000 description 6
- 239000004305 biphenyl Substances 0.000 description 6
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- 238000011156 evaluation Methods 0.000 description 6
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- 239000000178 monomer Substances 0.000 description 6
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 6
- ARTKJNDWFILKHT-UHFFFAOYSA-N 1-methoxy-2-(4-phenoxyphenyl)sulfanylbenzene Chemical compound O(C1=CC=CC=C1)C1=CC=C(C=C1)SC1=C(C=CC=C1)OC ARTKJNDWFILKHT-UHFFFAOYSA-N 0.000 description 5
- ZCHWYLUSYDXCOD-UHFFFAOYSA-N 1-methyl-2-(4-phenoxyphenyl)sulfanylbenzene Chemical compound CC1=C(C=CC=C1)SC1=CC=C(C=C1)OC1=CC=CC=C1 ZCHWYLUSYDXCOD-UHFFFAOYSA-N 0.000 description 5
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 5
- DJUXOBMAOGANPU-UHFFFAOYSA-N [4-(2-methylphenyl)sulfanylphenyl]-triphenylsilane Chemical compound C1(=CC=CC=C1)[Si](C1=CC=C(C=C1)SC1=C(C=CC=C1)C)(C1=CC=CC=C1)C1=CC=CC=C1 DJUXOBMAOGANPU-UHFFFAOYSA-N 0.000 description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 5
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
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- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
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- QQBDOJUNCZSRGA-UHFFFAOYSA-N phenyl-(4-phenylsulfanylphenyl)methanone Chemical compound C=1C=C(SC=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 QQBDOJUNCZSRGA-UHFFFAOYSA-N 0.000 description 4
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- GJKWGFQCMPENTI-UHFFFAOYSA-N trimethyl-[4-(2-methylphenyl)sulfinylphenyl]silane Chemical compound C[Si](C1=CC=C(C=C1)S(=O)C1=C(C=CC=C1)C)(C)C GJKWGFQCMPENTI-UHFFFAOYSA-N 0.000 description 4
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- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
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- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000005460 perfluorocycloalkyl group Chemical group 0.000 description 1
- 125000005459 perfluorocyclohexyl group Chemical group 0.000 description 1
- 125000005007 perfluorooctyl group Chemical group FC(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)* 0.000 description 1
- 125000005008 perfluoropentyl group Chemical group FC(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)* 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 125000004932 phenoxathinyl group Chemical group 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- UZRUZACOSHWLOC-UHFFFAOYSA-M phenoxyaluminum Chemical compound [Al]OC1=CC=CC=C1 UZRUZACOSHWLOC-UHFFFAOYSA-M 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920001289 polyvinyl ether Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 230000007261 regionalization Effects 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000010944 silver (metal) Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium group Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-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
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- CVNKFOIOZXAFBO-UHFFFAOYSA-J tin(4+);tetrahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[Sn+4] CVNKFOIOZXAFBO-UHFFFAOYSA-J 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-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
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000004360 trifluorophenyl group Chemical group 0.000 description 1
- VRRIVXLVXXAHJA-UHFFFAOYSA-N tris(2,3,4-tribromophenyl) phosphate Chemical compound BrC1=C(Br)C(Br)=CC=C1OP(=O)(OC=1C(=C(Br)C(Br)=CC=1)Br)OC1=CC=C(Br)C(Br)=C1Br VRRIVXLVXXAHJA-UHFFFAOYSA-N 0.000 description 1
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
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Abstract
Description
また、これらのオニウム塩は、熱あるいは活性エネルギー線照射によって酸を発生するので酸発生剤とも称され、レジストや感光性材料にも使用されている(特許文献11〜13)。
すなわち、本発明は、下記一般式(1)、(2)及び(3)で示される群から選ばれるスルホニウムカチオンと式(a)で示されるガレートアニオンからなるスルホニウム塩、該スルホニウム塩を含有することを特徴とする光酸発生剤、及び該光酸発生剤とカチオン重合性化合物とを含有してなる、エネルギー線硬化性組成物及びこれらを硬化してなる硬化体である。
HO(−AO)q− (5)
〔AOはエチレンオキシ基及び/又はプロピレンオキシ基、qは1〜5の整数を表す。〕
一般式(2)中、Xにおける、置換されてもよいチオキサントニル基としては、7−イソプロピルチオキサントニル、7−クロロチオキサントニル等が挙げられる。
Xのうち、好ましくは、置換されてもよいチオキサントニル基である。
これらの置換基は、一般式(1)中、R1〜R4において、上記に挙げられたものと同様である。
nは1〜3の整数であり、好ましくは1である。Qは単結合、-O-又は-S-であり、好ましくは-S-である。
ここでパーフルオロアルキル基の炭素数は1〜8、好ましくは1〜4である。パーフルオロアルキル基の具体例としてはトリフルオロメチル、ペンタフルオロエチル、ヘプタフルオロプロピル、ノナフルオロブチル、パーフルオロペンチル、パーフルオロオクチルなどの直鎖パーフルオロアルキル基;ヘプタフルオロイソプロピル、ノナフルオロイソブチル、ノナフルオロ−sec−ブチル、ノナフルオロ−tert−ブチルなどの分岐パーフルオロアルキル基;さらにパーフルオロシクロプロピル、パーフルオロシクロブチル、パーフルオロシクロペンチル、パーフルオロシクロヘキシルなどのパーフルオロシクロアルキル基などが挙げられる。
ここでパーフルオロアルコキシ基の炭素数は1〜8、好ましくは1〜4である。パーフルオロアルコキシ基の具体例としてはトリフルオロメトキシ、ペンタフルオロエトキシ、ヘプタフルオロプロポキシ、ノナフルオロブトキシ、パーフルオロペンチルオキシ、パーフルオロオクチルオキシなどの直鎖パーフルオロアルコキシ基;ヘプタフルオロイソプロポキシ、ノナフルオロイソブトキシ、ノナフルオロ−sec−ブトキシ、ノナフルオロ−tert−ブトキシなどの分岐パーフルオロアルコキシ基などが挙げられる。
ハロゲンとしては、フッ素、塩素、臭素、ヨウ素が挙げられる。
パーフルオロアルキル基としては上記のものが挙げられる。
カチオン重合性能の観点から、R13〜R16は、パーフルオロアルキル基及びフッ素原子からなる群より選ばれる少なくとも1種で置換されたフェニル基が好ましい。
これらのうち、ペンタフルオロフェニル基(C6F5)及びビス(トリフルオロメチル)フェニル基((CF3)2C6H3)がさらに好ましく、ペンタフルオロフェニル基が特に好ましい。
これらのポリオルガノシロキサンは、直鎖状、分岐鎖状、環状のいずれでもよく、これらの混合物であってもよい。
光安定剤としては、公知の光安定剤等が使用でき、紫外線吸収型安定剤{ベンゾトリアゾール、ベンゾフェノン、サリチレート、シアノアクリレート及びこれらの誘導体等};ラジカル補足型安定剤{ヒンダードアミン等};及び消光型安定剤{ニッケル錯体等}等が挙げられる。
酸化防止剤としては、公知の酸化防止剤等が使用でき、フェノール系酸化防止剤(モノフェノール系、ビスフェノール系及び高分子フェノール系等)、硫黄系酸化防止剤及びリン系酸化防止剤等が挙げられる。
密着性付与剤としては、公知の密着性付与剤等が使用でき、カップリング剤、シランカップリング剤及びチタンカップリング剤等が挙げられる。
イオン補足剤としては、公知のイオン補足剤等が使用でき、有機アルミニウム(アルコキシアルミニウム及びフェノキシアルミニウム等)等が挙げられる。
着色防止剤としては、公知の着色防止剤が使用でき、一般的には酸化防止剤が有効であり、フェノール系酸化防止剤(モノフェノール系、ビスフェノール系及び高分子フェノール系等)、硫黄系酸化防止剤及びリン系酸化防止剤等が挙げられる。
エネルギー線としては、本発明の光酸発生剤の分解を誘発するエネルギーを有する限りいかなるものでもよいが、低圧、中圧、高圧若しくは超高圧の水銀灯、メタルハライドランプ、LEDランプ、キセノンランプ、カーボンアークランプ、蛍光灯、半導体固体レーザ、アルゴンレーザ、He−Cdレーザ、KrFエキシマレーザ、ArFエキシマレーザ又はF2レーザ等から得られる紫外〜可視光領域(波長:約100〜約800nm)のエネルギー線が好ましい。なお、エネルギー線には、電子線又はX線等の高エネルギーを有する放射線を用いることもできる。
4−(フェニルチオ)ビフェニル2.0部を[4−(フェノキシ)フェニル](2−メトキシフェニル)スルフィド2.22部に、30%過酸化水素水溶液0.43部を30%過酸化水素水溶液0.46部に変更した以外、製造例1と同様にして、[4−(フェノキシ)フェニル](2−メトキシフェニル)スルフィドを42%と[4−(フェノキシ)フェニル](2−メトキシフェニル)スルホキシドを58%を含む混合物を得た。生成物の同定はカラムクロマトグラフィー(溶離液:酢酸エチル/ヘキサン=1/1:容量比)で単離した後、1H−NMRにて同定した。各化合物の含有量は混合物のHPLC分析によるピーク面積比より算出した。
窒素雰囲気下で十分に乾燥させた125mL4つ口フラスコに超脱水ジエチルエーテル360部及びペンタフルオロブロモベンゼン30部を仕込み、これをドライアイス/アセトン浴を用いて−78℃に冷却した。2.5mol/Lのn−ブチルリチウムヘキサン溶液70部を10分かけて滴下し、その後、−78℃で30分撹拌した。これに、塩化ガリウム(III)5部を溶解させたジエチルエーテル溶液68部を10分かけて滴下し、−78℃で3時間撹拌した。反応液を徐々に室温に戻しながら攪拌し、室温に戻してから更に5時間撹拌した。析出した固体をろ過し、反応液をエバポレーターに移し溶媒を留去することにより、灰白色の生成物を得た。生成物を超脱水ヘキサン50部で4回洗浄した後、一晩真空乾燥させ、テトラキス(ペンタフルオロフェニル)ガレートリチウムを得た。生成物は19F−NMRにて同定した。
ペンタフルオロブロモベンゼン30部を1−ブロモ−3,5−ビス(トリフルオロメチル)ベンゼン35.6部に変更した以外、製造例12と同様にして、テトラキス(3,5−ビス(トリフルオロメチル)フェニル)ガレートリチウムを得た。生成物は19F−NMRにて同定した。
製造例4で製造した[4−(フェノキシ)フェニル]フェニルスルフィドを49%と[4−(フェノキシ)フェニル]フェニルスルホキシドを51%含む混合物5.2部をメタンスルホン酸15.5部に溶解し、室温で無水酢酸2.8部を滴下した。その後、60℃で6時間攪拌した。反応溶液を室温まで冷却後、イオン交換水200部中に投入し、ジクロロメタン100部で抽出し、水層のpHが中性になるまでイオン交換水で洗浄した。ここで、攪拌下、リチウムテトラキス(ペンタフルオロフェニル)ガレート8.8部を加え、室温で3時間撹拌した。ジクロロメタン層をイオン交換水で3回洗浄し、ジクロロメタン層をロータリーエバポレーターに移して溶媒を留去後、残渣をトルエン/ヘキサン溶液で洗浄することにより、A−7を得た。生成物は1H−NMRにて同定した。
製造例7で製造した[4−(トリメチルシリル)フェニル]フェニルスルフィドを48.5%と[4−(トリメチルシリル)フェニル]フェニルスルホキシドを51.5%含む混合物4.8部及びメタンスルホン酸23.3部を仕込み、室温で無水酢酸2.8部を滴下した。その後、60℃で6時間攪拌し、反応溶液を室温まで冷却後、イオン交換水200部中に投入し、ジクロロメタン100部で抽出し、水層のpHが中性になるまでイオン交換水で洗浄した。ここで、攪拌下、リチウムテトラキス(ペンタフルオロフェニル)ガレート8.8部を加え、室温で3時間撹拌した。ジクロロメタン層を分液操作にてイオン交換水で3回洗浄し、ロータリーエバポレーターに移して溶媒を留去後、残渣をトルエン/ヘキサン溶液で洗浄することにより、A−13を得た。生成物は1H−NMRにて同定した。
(4−フェニルチオ)フェニル ジフェニルスルホニウム トリフルオロメタンスルホネート32.0部を含むジクロロメタン溶液89部を、塩化アルミニウム36.8部、アセチルクロライド12.0部、ジクロロメタン200部を混合した懸濁液中に攪拌、冷却下、系内温度が10℃を超えないように滴下した。滴下終了後、室温で2時間攪拌し、攪拌下反応液を冷水300部中に投入した。上層を取り除き、ジクロロメタン層を水層のpHが中性になるまでイオン交換水で洗浄した。ここで、攪拌下、テトラキス(ペンタフルオロフェニル)ガレートリチウム5.5部を加え、室温で1時間攪拌した。ジクロロメタン層を分液操作にてイオン交換水で3回洗浄した後、ロータリーエバポレーターに移して溶媒を留去後、残渣をトルエン/ヘキサン溶液で洗浄することにより、A−25を得た。生成物は1H−NMRにて同定した。
2−(フェニルチオ)チオキサントン4.3部、2−[(フェニル)スルフィニル]チオキサントン4.5部、無水酢酸4.1部及びアセトニトリル110部を仕込み、トリフルオロメタンスルホン酸2.4部を徐々に滴下し、40〜45℃で1時間攪拌した。反応溶液を室温まで冷却し、イオン交換水150部中に投入し、ジクロロメタン50部で抽出し、水相のpHが中性になるまでイオン交換水で洗浄した。ジクロロメタン層をロータリーエバポレーターに移して溶媒を留去した後、トルエン50部を加えて超音波洗浄器でトルエン中に分散し、15分間静置してから上澄みを除く操作を3回繰り返して、生成した固体を洗浄した。固体をロータリーエバポレーターに移して、溶媒を留去することにより、[4−(2−チオキサントニルチオ)フェニル]フェニル−2−チオキサントニルスルホニウム トリフレート(トリフレート=トリフルオロメタンスルホン酸アニオン)を得た。
(複分解法)このトリフレート及びリチウムテトラキス(ペンタフルオロフェニル)ガレート10.9部をジクロロメタン50部中に投入し、室温で3時間撹拌した。ジクロロメタン層を分液操作にてイオン交換水で3回洗浄した後、ジクロロメタン層をロータリーエバポレーターに移して溶媒を留去することにより、A−29を得た。構造は1H−NMRにて同定した。
リチウムテトラキス(ペンタフルオロフェニル)ガレート10.9部をリチウムテトラキス(3,5−ビス(トリフルオロメチル)フェニル)ガレート13.2部に変更したこと以外、実施例29と同様にして、A−30を得た。構造は1H−NMRにて同定した。
リチウムテトラキス(ペンタフルオロフェニル)ガレート33.4部をリチウムテトラキス(3,5−ビス(トリフルオロメチル)フェニル)ガレート40.5部に変更したこと以外、実施例31と同様にして、A−32を得た。構造は1H−NMRにて同定した。
(硬化性組成物の調製)
本発明の光酸発生剤及び比較例の化合物を、カチオン重合性化合物であるエポキシド(3,4−エポキシシクロヘキシルメチル−3,4−エポキシシクロヘキサンカルボキシレート、ダイセル化学工業株式会社製、セロキサイド2021P)及びビスフェノールA(4,4'−(プロパン−2,2−ジイル)ジフェノール、出光興産株式会社製)を表1に示した配合量で均一混合して、本発明の硬化性組成物1〜38及び比較用の硬化性組成物39〜41を調整した。
上記で得た、本発明の硬化性組成物1〜38及び比較用の硬化性組成物39〜41をアプリケーター(40μm)でポリエチレンテレフタレート(PET)フィルムに塗布した。PETフィルムに紫外線照射装置を用いて、フィルターによって波長を限定した紫外光を照射した。なお、フィルターは365フィルター(アイグラフィックス株式会社製、365nm未満の光をカットするフィルター)を使用した。照射後、40分後の塗膜硬度を鉛筆硬度(JIS K5600−5−4:1999)にて測定し、以下の基準により評価した(硬化後の塗膜厚は約40μm)。
(判定基準)
◎:鉛筆硬度が2H以上
○:鉛筆硬度がH〜B
△:鉛筆硬度が2B〜4B
×:液状〜タックがあり、鉛筆硬度を測定できない
・紫外線照射装置:ベルトコンベア式UV照射装置(アイグラフィックス株式会社製)
・ランプ:1.5kW高圧水銀灯
・フィルター:365フィルター(アイグラフィックス株式会社製)
・照度(365nmヘッド照度計で測定):100mW/cm2
・積算光量(365nmヘッド照度計で測定):300mJ/cm2
上記で得た組成物をアプリケーターにてスライドガラス上に膜厚40μmで塗布した。上記塗布後のスライドガラスに紫外線照射装置を用いて、紫外線を照射した。
(紫外光の照射条件)
・紫外線照射装置:ベルトコンベア式UV照射装置(アイグラフィックス株式会社製)
・ランプ:1.5kW高圧水銀灯
・照度(365nmヘッド照度計で測定):100mW/cm2
・積算光量(365nmヘッド照度計で測定):1000mJ/cm2
照射後40分間室温で硬化させた後、ホットプレートにて120℃×30分間アフターキュアーして耐熱試験用のサンプルを作成した。
このサンプルを240℃に温調したホットプレートにて15分間加熱し、塗膜の色相を目視で評価した。評価基準は下記の通り。
◎:無色(塗膜の黄変なし)
○:淡黄色〜黄色
×:褐色
上記で得た組成物をアプリケーターにてCu基板上に膜厚40μmで塗布した。上記塗布後のCu基板に紫外線照射装置を用いて、紫外線を照射した。
(紫外光の照射条件)
・紫外線照射装置:ベルトコンベア式UV照射装置(アイグラフィックス株式会社製)
・ランプ:1.5kW高圧水銀灯
・照度(365nmヘッド照度計で測定):100mW/cm2
・積算光量(365nmヘッド照度計で測定):1000mJ/cm2
照射後、ホットプレートにて120℃×15分間アフターキュアーして金属腐食試験用のサンプルを作成した。
このサンプルについて、80℃/85%の湿熱条件下にて、720時間放置し、金属腐食試験を実施した。試験後の基板について、金属腐食の有無を目視で評価した。評価基準は下記の通り。
◎:目視でCu基板の色変化は全くわからなかった。
○:目視でCu基板の色変化はうっすら感じられた。
△:目視でCu基板が少し黒っぽく見えた。
×:Cu基板が真っ黒に変色していた。
Claims (14)
- 下記一般式(1)、(2)及び(3)で示される群から選ばれるスルホニウムカチオンと式(a)で示されるガレートアニオンからなるスルホニウム塩。
- 一般式(1)において、R1がアルキルカルボニル基、アリール基、シリル基、アリールカルボニル基及びアリールオキシ基から選ばれる基である請求項1に記載のスルホニウム塩。
- 一般式(1)において、R1がアリール基及びアルキルカルボニル基である請求項1に記載のスルホニウム塩。
- 一般式(1)において、aが1である請求項1〜3の何れかに記載のスルホニウム塩。
- 一般式(1)において、aが1、b〜dが0である請求項1〜4の何れかに記載のスルホニウム塩。
- 一般式(1)において、R1及びR3がそれぞれ独立に、アルキルカルボニル基、アリール基、シリル基、アリールカルボニル基及びアリールオキシ基から選ばれる基であり、a及びcが1である請求項1〜4の何れかに記載のスルホニウム塩。
- 一般式(2)において、Xが置換されてもよいチオキサントニル基であり、Yが-S-である請求項1〜6の何れかに記載のスルホニウム塩。
- 一般式(2)において、e、f、g及びhが0である請求項7に記載のスルホニウム塩。
- 一般式(3)において、nが1であり、Qが-S-であり、i及びjが0であり、Arがフェニル基である請求項1〜8の何れかに記載のスルホニウム塩。
- 式(a)において、R13〜R16がパーフルオロアルキル基及びフッ素原子からなる群より選ばれる少なくとも1種で置換されたフェニル基である請求項1〜9の何れかに記載のスルホニウム塩。
- 式(a)において、[ (R13)( R14)( R15)( R16)Ga]−で表されるガレートアニオンが[Ga(C6F5)4]―又は、[Ga((CF3)2C6H3)4]―である請求項1〜10の何れかに記載のスルホニウム塩。
- 請求項1〜11の何れかに記載のスルホニウム塩を含有することを特徴とする光酸発生剤。
- 請求項12に記載の光酸発生剤とカチオン重合性化合物とを含んでなるエネルギー線硬化性組成物。
- 請求項13に記載のエネルギー線硬化性組成物を硬化させて得られることを特徴とする硬化体。
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JP5517658B2 (ja) * | 2010-02-09 | 2014-06-11 | サンアプロ株式会社 | スルホニウム塩,光酸発生剤,硬化性組成物及びポジ型フォトレジスト組成物 |
JP5828715B2 (ja) * | 2011-08-25 | 2015-12-09 | サンアプロ株式会社 | スルホニウム塩、光酸発生剤、硬化性組成物およびレジスト組成物 |
KR101274646B1 (ko) | 2011-12-28 | 2013-06-17 | 주식회사 씨앤케이 | 전기식 수중히터의 온도감지장치 |
WO2014061062A1 (ja) * | 2012-10-18 | 2014-04-24 | サンアプロ株式会社 | スルホニウム塩、光酸発生剤、硬化性組成物およびレジスト組成物 |
JP6046540B2 (ja) * | 2013-04-05 | 2016-12-14 | サンアプロ株式会社 | スルホニウム塩、光酸発生剤、硬化性組成物およびレジスト組成物 |
JP6708382B2 (ja) * | 2015-09-03 | 2020-06-10 | サンアプロ株式会社 | 硬化性組成物及びそれを用いた硬化体 |
WO2017039279A1 (ko) * | 2015-09-04 | 2017-03-09 | 주식회사 나노엔텍 | 샘플 전처리 모듈 및 이를 이용한 샘플 전처리 방법 |
US20210123297A1 (en) | 2018-06-26 | 2021-04-29 | Panasonic Intellectual Property Management Co., Ltd. | Method for manufacturing glass panel unit |
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