JP2016056168A - スルホニウム塩の製造方法 - Google Patents
スルホニウム塩の製造方法 Download PDFInfo
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- JP2016056168A JP2016056168A JP2015162810A JP2015162810A JP2016056168A JP 2016056168 A JP2016056168 A JP 2016056168A JP 2015162810 A JP2015162810 A JP 2015162810A JP 2015162810 A JP2015162810 A JP 2015162810A JP 2016056168 A JP2016056168 A JP 2016056168A
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- Prior art keywords
- sulfonium salt
- anion
- acid
- salt
- sulfonium
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 title claims abstract description 70
- 238000000034 method Methods 0.000 title claims abstract description 48
- -1 sulfonium cation Chemical class 0.000 claims abstract description 91
- 150000001450 anions Chemical class 0.000 claims abstract description 52
- 150000003839 salts Chemical class 0.000 claims abstract description 31
- 239000002253 acid Substances 0.000 claims description 29
- 238000004519 manufacturing process Methods 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 6
- 150000004820 halides Chemical class 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 229910017008 AsF 6 Inorganic materials 0.000 claims description 4
- 229910015892 BF 4 Inorganic materials 0.000 claims description 4
- 229910021115 PF 6 Inorganic materials 0.000 claims description 4
- 229910018286 SbF 6 Inorganic materials 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 abstract description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
- 239000010410 layer Substances 0.000 description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 229920002120 photoresistant polymer Polymers 0.000 description 15
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- 238000009713 electroplating Methods 0.000 description 11
- 239000012044 organic layer Substances 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- 238000006482 condensation reaction Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- JJHHIJFTHRNPIK-UHFFFAOYSA-N Diphenyl sulfoxide Chemical compound C=1C=CC=CC=1S(=O)C1=CC=CC=C1 JJHHIJFTHRNPIK-UHFFFAOYSA-N 0.000 description 8
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 8
- 150000007524 organic acids Chemical class 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 229940098779 methanesulfonic acid Drugs 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 150000007522 mineralic acids Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000007810 chemical reaction solvent Substances 0.000 description 4
- 238000007772 electroless plating Methods 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 150000003462 sulfoxides Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- GEJVCYBIKJCCME-UHFFFAOYSA-L S(=O)(=O)([O-])C(F)(F)C(F)(F)C(F)(F)C(F)(F)F.S(=O)(=O)([O-])C(F)(F)C(F)(F)C(F)(F)C(F)(F)F.C1(=CC=CC=C1)[S+](C1=CC=C(C=C1)SC1=CC=C(C=C1)[S+](C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound S(=O)(=O)([O-])C(F)(F)C(F)(F)C(F)(F)C(F)(F)F.S(=O)(=O)([O-])C(F)(F)C(F)(F)C(F)(F)C(F)(F)F.C1(=CC=CC=C1)[S+](C1=CC=C(C=C1)SC1=CC=C(C=C1)[S+](C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1 GEJVCYBIKJCCME-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical group CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 238000010813 internal standard method Methods 0.000 description 3
- 238000000206 photolithography Methods 0.000 description 3
- 238000007747 plating Methods 0.000 description 3
- LVTHXRLARFLXNR-UHFFFAOYSA-M potassium;1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound [K+].[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F LVTHXRLARFLXNR-UHFFFAOYSA-M 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 229920001187 thermosetting polymer Polymers 0.000 description 3
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- KJGYFISADIZFEL-UHFFFAOYSA-N 1-chloro-4-(4-chlorophenyl)sulfinylbenzene Chemical compound C1=CC(Cl)=CC=C1S(=O)C1=CC=C(Cl)C=C1 KJGYFISADIZFEL-UHFFFAOYSA-N 0.000 description 2
- GVYKABJIEOOUOX-UHFFFAOYSA-N 1-fluoro-4-(4-fluorophenyl)sulfinylbenzene Chemical compound C1=CC(F)=CC=C1S(=O)C1=CC=C(F)C=C1 GVYKABJIEOOUOX-UHFFFAOYSA-N 0.000 description 2
- NQMUGNMMFTYOHK-UHFFFAOYSA-N 1-methoxynaphthalene Chemical group C1=CC=C2C(OC)=CC=CC2=C1 NQMUGNMMFTYOHK-UHFFFAOYSA-N 0.000 description 2
- MJWNJEJCQHNDNM-UHFFFAOYSA-N 1-methyl-4-(4-methylphenyl)sulfinylbenzene Chemical compound C1=CC(C)=CC=C1S(=O)C1=CC=C(C)C=C1 MJWNJEJCQHNDNM-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical group C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical group C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- TURIHPLQSRVWHU-UHFFFAOYSA-N 2-phenylnaphthalene Chemical group C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=C1 TURIHPLQSRVWHU-UHFFFAOYSA-N 0.000 description 2
- RQCACQIALULDSK-UHFFFAOYSA-N 4-(4-hydroxyphenyl)sulfinylphenol Chemical compound C1=CC(O)=CC=C1S(=O)C1=CC=C(O)C=C1 RQCACQIALULDSK-UHFFFAOYSA-N 0.000 description 2
- ZSBDGXGICLIJGD-UHFFFAOYSA-N 4-phenoxyphenol Chemical group C1=CC(O)=CC=C1OC1=CC=CC=C1 ZSBDGXGICLIJGD-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- MIKBRXYSXMTJDS-UHFFFAOYSA-M CS(=O)(=O)[O-].C1(=CC=CC=C1)[S+](C1=CC=C(C=C1)SC1=CC=CC=C1)C1=CC=CC=C1 Chemical compound CS(=O)(=O)[O-].C1(=CC=CC=C1)[S+](C1=CC=C(C=C1)SC1=CC=CC=C1)C1=CC=CC=C1 MIKBRXYSXMTJDS-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical group CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical group C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical group COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical group C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- 125000005110 aryl thio group Chemical group 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- QDHFHIQKOVNCNC-UHFFFAOYSA-N butane-1-sulfonic acid Chemical compound CCCCS(O)(=O)=O QDHFHIQKOVNCNC-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000010538 cationic polymerization reaction Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical group CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 239000012024 dehydrating agents Substances 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- NGDPCAMPVQYGCW-UHFFFAOYSA-N dibenzothiophene 5-oxide Chemical compound C1=CC=C2S(=O)C3=CC=CC=C3C2=C1 NGDPCAMPVQYGCW-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical group C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical group C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
- FEELUMNBAODGBA-UHFFFAOYSA-M diphenyl-(4-phenylsulfanylphenyl)sulfanium;1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical group [O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F.C=1C=C([S+](C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1SC1=CC=CC=C1 FEELUMNBAODGBA-UHFFFAOYSA-M 0.000 description 2
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- WLGDAKIJYPIYLR-UHFFFAOYSA-N octane-1-sulfonic acid Chemical compound CCCCCCCCS(O)(=O)=O WLGDAKIJYPIYLR-UHFFFAOYSA-N 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- RJQRCOMHVBLQIH-UHFFFAOYSA-M pentane-1-sulfonate Chemical compound CCCCCS([O-])(=O)=O RJQRCOMHVBLQIH-UHFFFAOYSA-M 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical group C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 229910000679 solder Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical group CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- DHQZCWAORMPMSI-UHFFFAOYSA-N (1,2,3,4,5,5,6,6-octafluorocyclohex-2-en-1-yl)oxyboronic acid Chemical compound FC1(C(C(C(=C(C1F)F)F)(OB(O)O)F)(F)F)F DHQZCWAORMPMSI-UHFFFAOYSA-N 0.000 description 1
- DMEMLCJAORAIFA-UHFFFAOYSA-N (2-methylphenyl)-(2-phenylsulfanylphenyl)methanethione Chemical compound CC1=CC=CC=C1C(=S)C1=CC=CC=C1SC1=CC=CC=C1 DMEMLCJAORAIFA-UHFFFAOYSA-N 0.000 description 1
- OVIAOYLSBJBPSY-UHFFFAOYSA-N (3-chloro-4-phenylsulfanylphenyl)-phenylmethanone Chemical compound ClC1=CC(C(=O)C=2C=CC=CC=2)=CC=C1SC1=CC=CC=C1 OVIAOYLSBJBPSY-UHFFFAOYSA-N 0.000 description 1
- WGBYOWIYAKVOLO-UHFFFAOYSA-N 1,4-bis(phenylsulfanyl)benzene Chemical compound C=1C=C(SC=2C=CC=CC=2)C=CC=1SC1=CC=CC=C1 WGBYOWIYAKVOLO-UHFFFAOYSA-N 0.000 description 1
- NBNQTORHACKHCW-UHFFFAOYSA-N 1-(benzenesulfinyl)-4-methylbenzene Chemical compound C1=CC(C)=CC=C1S(=O)C1=CC=CC=C1 NBNQTORHACKHCW-UHFFFAOYSA-N 0.000 description 1
- AZFFUGUTCQGAAW-UHFFFAOYSA-N 1-(benzenesulfinyl)-4-phenylsulfanylbenzene Chemical compound C=1C=C(SC=2C=CC=CC=2)C=CC=1S(=O)C1=CC=CC=C1 AZFFUGUTCQGAAW-UHFFFAOYSA-N 0.000 description 1
- VAIMIWMAVGWBGX-UHFFFAOYSA-N 1-bromo-2-(2-bromophenyl)sulfanylbenzene Chemical compound BrC1=CC=CC=C1SC1=CC=CC=C1Br VAIMIWMAVGWBGX-UHFFFAOYSA-N 0.000 description 1
- FGPSFZNISIIDND-UHFFFAOYSA-N 1-bromo-3-phenylsulfanylbenzene Chemical compound BrC1=CC=CC(SC=2C=CC=CC=2)=C1 FGPSFZNISIIDND-UHFFFAOYSA-N 0.000 description 1
- YNJLAXHIFOICPE-UHFFFAOYSA-N 1-chloro-3-phenylsulfanylbenzene Chemical compound ClC1=CC=CC(SC=2C=CC=CC=2)=C1 YNJLAXHIFOICPE-UHFFFAOYSA-N 0.000 description 1
- RKMZTRDJSKGOCM-UHFFFAOYSA-N 1-chloro-4-phenylsulfanylbenzene Chemical compound C1=CC(Cl)=CC=C1SC1=CC=CC=C1 RKMZTRDJSKGOCM-UHFFFAOYSA-N 0.000 description 1
- PLMKPWXDMAOTPF-UHFFFAOYSA-N 1-methoxy-2-phenylsulfanylbenzene Chemical compound COC1=CC=CC=C1SC1=CC=CC=C1 PLMKPWXDMAOTPF-UHFFFAOYSA-N 0.000 description 1
- LEDPSBGADKSDKI-UHFFFAOYSA-N 1-methoxy-4-(4-methoxyphenyl)sulfinylbenzene Chemical compound C1=CC(OC)=CC=C1S(=O)C1=CC=C(OC)C=C1 LEDPSBGADKSDKI-UHFFFAOYSA-N 0.000 description 1
- KXCVWFIROSGRRF-UHFFFAOYSA-N 1-methyl-2-phenylsulfanylbenzene Chemical compound CC1=CC=CC=C1SC1=CC=CC=C1 KXCVWFIROSGRRF-UHFFFAOYSA-N 0.000 description 1
- CPZFPNKPHBCUOB-UHFFFAOYSA-N 1-methyl-4-phenylsulfanylbenzene Chemical compound C1=CC(C)=CC=C1SC1=CC=CC=C1 CPZFPNKPHBCUOB-UHFFFAOYSA-N 0.000 description 1
- VTRRCXRVEQTTOE-UHFFFAOYSA-N 1-methylsulfinylethane Chemical compound CCS(C)=O VTRRCXRVEQTTOE-UHFFFAOYSA-N 0.000 description 1
- CFPMTYLOUSWLLM-UHFFFAOYSA-N 1-naphthalen-2-ylnaphthalene Chemical group C1=CC=C2C(C3=CC4=CC=CC=C4C=C3)=CC=CC2=C1 CFPMTYLOUSWLLM-UHFFFAOYSA-N 0.000 description 1
- FOPAYJWJHKMOHS-UHFFFAOYSA-N 1-nitro-4-(4-nitrophenyl)sulfinylbenzene Chemical compound C1=CC([N+](=O)[O-])=CC=C1S(=O)C1=CC=C([N+]([O-])=O)C=C1 FOPAYJWJHKMOHS-UHFFFAOYSA-N 0.000 description 1
- MRLUWCIEBHJONW-UHFFFAOYSA-N 1-phenyl-2-phenylsulfanylethanone Chemical group C=1C=CC=CC=1C(=O)CSC1=CC=CC=C1 MRLUWCIEBHJONW-UHFFFAOYSA-N 0.000 description 1
- AZTMYBHDPKCGQE-UHFFFAOYSA-N 1-phenylsulfanyl-4-(4-phenylsulfanylphenyl)benzene Chemical group C=1C=C(C=2C=CC(SC=3C=CC=CC=3)=CC=2)C=CC=1SC1=CC=CC=C1 AZTMYBHDPKCGQE-UHFFFAOYSA-N 0.000 description 1
- GUMOJENFFHZAFP-UHFFFAOYSA-N 2-Ethoxynaphthalene Chemical group C1=CC=CC2=CC(OCC)=CC=C21 GUMOJENFFHZAFP-UHFFFAOYSA-N 0.000 description 1
- NOYRFDHEJYWIHG-UHFFFAOYSA-N 2-methoxythioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(OC)=CC=C3SC2=C1 NOYRFDHEJYWIHG-UHFFFAOYSA-N 0.000 description 1
- APWYHOPXAIRDIZ-UHFFFAOYSA-N 2-phenylsulfanylnaphthalene Chemical compound C=1C=C2C=CC=CC2=CC=1SC1=CC=CC=C1 APWYHOPXAIRDIZ-UHFFFAOYSA-N 0.000 description 1
- KTALPKYXQZGAEG-UHFFFAOYSA-N 2-propan-2-ylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC=C3SC2=C1 KTALPKYXQZGAEG-UHFFFAOYSA-N 0.000 description 1
- VZNHRVXOOXDJPK-UHFFFAOYSA-N 9-phenylsulfanylanthracene Chemical compound C=12C=CC=CC2=CC2=CC=CC=C2C=1SC1=CC=CC=C1 VZNHRVXOOXDJPK-UHFFFAOYSA-N 0.000 description 1
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical group C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
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- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 1
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 1
- LKMCJXXOBRCATQ-UHFFFAOYSA-N benzylsulfanylbenzene Chemical group C=1C=CC=CC=1CSC1=CC=CC=C1 LKMCJXXOBRCATQ-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- CJTDSJQBAVLBAG-UHFFFAOYSA-N bis(4-phenylphenyl)methanethione Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=S)C(C=C1)=CC=C1C1=CC=CC=C1 CJTDSJQBAVLBAG-UHFFFAOYSA-N 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 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
- 150000001768 cations Chemical class 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- ABZDICOQQVXTQP-UHFFFAOYSA-M diphenyl-(4-phenylsulfanylphenyl)sulfanium;bromide Chemical compound [Br-].C=1C=C([S+](C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1SC1=CC=CC=C1 ABZDICOQQVXTQP-UHFFFAOYSA-M 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical group CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 1
- 239000008151 electrolyte solution Substances 0.000 description 1
- AEHWKBXBXYNPCX-UHFFFAOYSA-N ethylsulfanylbenzene Chemical group CCSC1=CC=CC=C1 AEHWKBXBXYNPCX-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Chemical group C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 125000002425 furfuryl group Chemical group C(C1=CC=CO1)* 0.000 description 1
- MBAKFIZHTUAVJN-UHFFFAOYSA-I hexafluoroantimony(1-);hydron Chemical compound F.F[Sb](F)(F)(F)F MBAKFIZHTUAVJN-UHFFFAOYSA-I 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- BICAGYDGRXJYGD-UHFFFAOYSA-N hydrobromide;hydrochloride Chemical compound Cl.Br BICAGYDGRXJYGD-UHFFFAOYSA-N 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052809 inorganic oxide Inorganic materials 0.000 description 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Chemical group COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- JCDWETOKTFWTHA-UHFFFAOYSA-N methylsulfonylbenzene Chemical group CS(=O)(=O)C1=CC=CC=C1 JCDWETOKTFWTHA-UHFFFAOYSA-N 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 150000002815 nickel Chemical class 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([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
- 238000000059 patterning Methods 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical group CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- GJSGGHOYGKMUPT-UHFFFAOYSA-N phenoxathiine Chemical compound C1=CC=C2OC3=CC=CC=C3SC2=C1 GJSGGHOYGKMUPT-UHFFFAOYSA-N 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- BOTNYLSAWDQNEX-UHFFFAOYSA-N phenoxymethylbenzene Chemical group C=1C=CC=CC=1COC1=CC=CC=C1 BOTNYLSAWDQNEX-UHFFFAOYSA-N 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910001392 phosphorus oxide Inorganic materials 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- PNGLEYLFMHGIQO-UHFFFAOYSA-M sodium;3-(n-ethyl-3-methoxyanilino)-2-hydroxypropane-1-sulfonate;dihydrate Chemical compound O.O.[Na+].[O-]S(=O)(=O)CC(O)CN(CC)C1=CC=CC(OC)=C1 PNGLEYLFMHGIQO-UHFFFAOYSA-M 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical group C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- ISXOBTBCNRIIQO-UHFFFAOYSA-N tetrahydrothiophene 1-oxide Chemical compound O=S1CCCC1 ISXOBTBCNRIIQO-UHFFFAOYSA-N 0.000 description 1
- VSAISIQCTGDGPU-UHFFFAOYSA-N tetraphosphorus hexaoxide Chemical compound O1P(O2)OP3OP1OP2O3 VSAISIQCTGDGPU-UHFFFAOYSA-N 0.000 description 1
- HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical group CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 125000005409 triarylsulfonium group Chemical group 0.000 description 1
- 239000008096 xylene Chemical group 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
しかし、従来提案されているスルホニウム塩の製造方法では、例えば、硫酸などの無機酸及びメタンスルホン酸などの強有機酸のうちの少なくともいずれかの酸の存在下、スルフィドとスルホキシドとを縮合させた後、強有機酸由来のアニオンを、フッ素含有アニオンと交換させる方法(例えば、特許文献1参照)が知られている。この方法では、1分子中に1個のスルホニオ基を有するモノスルホニウム塩以外に、1分子中に2個のスルホニオ基を有するビススルホニウム塩が生成する。
好ましくは、前記スルホニウムカチオンは、少なくとも1つのアリール基を有する。
好ましくは、前記第1スルホニウム塩を、スルホキシド化合物とアリール化合物とを酸の存在下で縮合させることにより生成する。
好ましくは、前記スルホキシド化合物は、置換されていてもよいジアリールスルホキシド化合物である。
好ましくは、前記アリール化合物は、置換されていてもよいジアリールスルフィド化合物である。
好ましくは、前記酸は、硫酸又はスルホン酸である。
好ましくは、前記第2スルホニウム塩を、前記ハロゲン化物イオンを含むハロゲン化物を前記第1スルホニウム塩と反応させることによって生成する。
好ましくは、前記第3スルホニウム塩を、第2アニオンを含む金属塩を第2スルホニウム塩反応させることによって生成する。
好ましくは、前記第2アニオンは、少なくとも1つのフッ素原子を含む。
好ましくは、前記第2アニオンは、CF3SO3 −、CF3CF2CF2CF2SO3 −、AsF6 −、PF6 −、SbF6 −、BF4 −及びB(C6F5)4 −からなる群から選択される1つである。
本発明の一実施形態のスルホニウム塩の製造方法は、スルホニウムカチオンと第1アニオンとを含む第1スルホニウム塩を生成し、前記第1アニオンをハロゲン化物イオンと交換して第2スルホニウム塩を生成し、前記ハロゲン化物イオンを第2アニオンと交換して第3スルホニウム塩を生成する工程を備える。
この工程では、スルホニウムカチオンと第1アニオンとを含む第1スルホニウム塩を生成する。スルホニウムカチオンは、下記一般式(1)で表される。第1アニオンは、スルホニウムカチオンの対アニオンとなりかつ、第2アニオンの共役酸よりも弱酸を発生するアニオンである。
この工程では、第1スルホニウム塩の第1アニオンをハロゲン化物イオンと交換して第2スルホニウム塩を生成する。
この工程では、第2スルホニウム塩のハロゲン化物イオンを第2アニオンと交換して第3スルホニウム塩を生成する。
ここで、上記方法で製造したスルホニウム塩を光酸発生剤として含むフォトレジストを用いた電解めっき工程について説明する。フォトレジストは、ポリマーと、上記スルホニウム塩を含む。ポリマーは、一例では、下記ポリマーAとポリマーBを含む。スルホニウム塩の一例は、後述する実施例で得られるジフェニル[4−(フェニルチオ)フェニル]−スルホニウムノナフレートである。電解めっき工程は、集積回路(IC)のようなデバイスの製造プロセスに含まれる工程である。この電解めっき工程では、フォトリソグラフィープロセスによって形成されるスルーホールに導電部が形成される。
20.0gの上記(2)で得られたPSDPS−Br及び15.7gのカリウムノナフレートを40gの水及び80gのジクロロメタンからなる2層溶媒へ添加した。得られた混合物を25℃で1時間攪拌することによって、PSDPS−Nfをジクロロメタン層中に抽出し、ジクロロメタン層を回収した。その後、ジクロロメタン層からなるジクロロメタン溶液を水で2回洗浄し、ジクロロメタンを留去した。それによって26.3gのPSDPS−Nfを得た。HPLCを用いて内部標準法によって生成物の純度を測定した。その結果、0.2%のビス−[4−(ジフェニルスルホニオ)フェニル]−スルフィドビス−ノナフレートが不純物として生成物に含まれていることが確認された。
Claims (10)
- スルホニウムカチオンと第1アニオンとを含む第1スルホニウム塩を生成し、
前記第1アニオンをハロゲン化物イオンと交換して第2スルホニウム塩を生成し、
前記ハロゲン化物イオンを第2アニオンと交換して第3スルホニウム塩を生成する工程を備える、スルホニウム塩の製造方法。 - 前記スルホニウムカチオンは、少なくとも1つのアリール基を有する、請求項1に記載の方法。
- 前記第1スルホニウム塩を、スルホキシド化合物とアリール化合物とを酸の存在下で縮合させることにより生成する、請求項1又は請求項2に記載の方法。
- 前記スルホキシド化合物は、置換されていてもよいジアリールスルホキシド化合物である、請求項3に記載の方法。
- 前記アリール化合物は、置換されていてもよいジアリールスルフィド化合物である、請求項3又は請求項4に記載の方法。
- 前記酸は、硫酸又はスルホン酸である、請求項3〜請求項5の何れか1つに記載の方法。
- 前記第2スルホニウム塩を、前記ハロゲン化物イオンを含むハロゲン化物を前記第1スルホニウム塩と反応させることによって生成する、請求項1〜請求項6の何れか1つに記載の方法。
- 前記第3スルホニウム塩を、第2アニオンを含む金属塩を第2スルホニウム塩反応させることによって生成する、請求項1〜請求項7の何れか1つに記載の方法。
- 前記第2アニオンは、少なくとも1つのフッ素原子を含む、請求項1〜請求項8の何れか1つに記載の方法。
- 前記第2アニオンは、CF3SO3 −、CF3CF2CF2CF2SO3 −、AsF6 −、PF6 −、SbF6 −、BF4 −及びB(C6F5)4 −からなる群から選択される1つである、請求項1〜請求項9の何れか1つに記載の方法。
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WO2011070947A1 (ja) * | 2009-12-08 | 2011-06-16 | Jsr株式会社 | 感放射線性樹脂組成物、重合体、単量体及び感放射線性樹脂組成物の製造方法 |
JP2013075963A (ja) * | 2011-09-29 | 2013-04-25 | Jsr Corp | 化合物、重合体及びフォトレジスト組成物 |
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