JP5149236B2 - 芳香族環を含む酸発生剤 - Google Patents
芳香族環を含む酸発生剤 Download PDFInfo
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- JP5149236B2 JP5149236B2 JP2009101787A JP2009101787A JP5149236B2 JP 5149236 B2 JP5149236 B2 JP 5149236B2 JP 2009101787 A JP2009101787 A JP 2009101787A JP 2009101787 A JP2009101787 A JP 2009101787A JP 5149236 B2 JP5149236 B2 JP 5149236B2
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- 239000002253 acid Substances 0.000 title claims description 48
- 125000003118 aryl group Chemical group 0.000 title claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 149
- 239000000126 substance Substances 0.000 claims description 128
- 238000006243 chemical reaction Methods 0.000 claims description 64
- -1 alcohol compound Chemical class 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 150000001875 compounds Chemical group 0.000 claims description 29
- 239000002904 solvent Substances 0.000 claims description 28
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 22
- 125000005843 halogen group Chemical group 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 15
- 125000002947 alkylene group Chemical group 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229920001774 Perfluoroether Polymers 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 11
- 150000001450 anions Chemical group 0.000 claims description 10
- 229910052708 sodium Inorganic materials 0.000 claims description 9
- 239000011734 sodium Substances 0.000 claims description 9
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 8
- 150000001768 cations Chemical class 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 229910052700 potassium Inorganic materials 0.000 claims description 7
- 239000003638 chemical reducing agent Substances 0.000 claims description 6
- 229910052744 lithium Inorganic materials 0.000 claims description 6
- 125000002950 monocyclic group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000003367 polycyclic group Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000005581 pyrene group Chemical group 0.000 claims description 5
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 4
- 230000001476 alcoholic effect Effects 0.000 claims description 4
- 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 claims description 4
- 150000002500 ions Chemical class 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 4
- 239000012279 sodium borohydride Substances 0.000 claims description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 3
- 229910015892 BF 4 Inorganic materials 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004036 acetal group Chemical group 0.000 claims description 3
- 125000003172 aldehyde group Chemical group 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000003700 epoxy group Chemical group 0.000 claims description 3
- 125000004185 ester group Chemical group 0.000 claims description 3
- 125000001033 ether group Chemical group 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 125000002560 nitrile group Chemical group 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 3
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 229910010199 LiAl Inorganic materials 0.000 claims description 2
- 229910010082 LiAlH Inorganic materials 0.000 claims description 2
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Inorganic materials [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 8
- 230000015572 biosynthetic process Effects 0.000 description 44
- 238000003786 synthesis reaction Methods 0.000 description 44
- 238000005481 NMR spectroscopy Methods 0.000 description 41
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 238000005160 1H NMR spectroscopy Methods 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 20
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000009792 diffusion process Methods 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 150000002430 hydrocarbons Chemical group 0.000 description 13
- 159000000000 sodium salts Chemical class 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- PREAJPIKNPDDON-APAIHEESSA-N dideuterio-[dichloro(deuterio)methyl]-lambda3-chlorane Chemical compound C(Cl([2H])[2H])(Cl)(Cl)[2H] PREAJPIKNPDDON-APAIHEESSA-N 0.000 description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- FSXZQFLOCVYAKF-UHFFFAOYSA-N benzhydrylsulfanylbenzene;sodium;trifluoromethanesulfonic acid Chemical compound [Na].OS(=O)(=O)C(F)(F)F.C=1C=CC=CC=1SC(C=1C=CC=CC=1)C1=CC=CC=C1 FSXZQFLOCVYAKF-UHFFFAOYSA-N 0.000 description 8
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- 239000004305 biphenyl Substances 0.000 description 6
- 235000010290 biphenyl Nutrition 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 0 *CC[C@](C1)(C1C1CCCC1)[C@]1[C@](CC2)[C@@]2C1 Chemical compound *CC[C@](C1)(C1C1CCCC1)[C@]1[C@](CC2)[C@@]2C1 0.000 description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 4
- MXNBDFWNYRNIBH-UHFFFAOYSA-N 3-fluorobenzoic acid Chemical compound OC(=O)C1=CC=CC(F)=C1 MXNBDFWNYRNIBH-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 239000007810 chemical reaction solvent Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000035699 permeability Effects 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- OVGMTYOPHVFYEG-UHFFFAOYSA-M sodium 1,2-difluoro-1-hydroxyethanesulfonate Chemical compound [Na+].FCC(S(=O)(=O)[O-])(O)F OVGMTYOPHVFYEG-UHFFFAOYSA-M 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- NRPFNQUDKRYCNX-UHFFFAOYSA-N 4-methoxyphenylacetic acid Chemical compound COC1=CC=C(CC(O)=O)C=C1 NRPFNQUDKRYCNX-UHFFFAOYSA-N 0.000 description 2
- SBZKKRAVIDMFNA-UHFFFAOYSA-L C1=CC=C(C=C1)CC(=S)OCC(F)(F)S(=O)(=O)[O-].C1=CC=C(C=C1)CC(=S)OCC(F)(F)S(=O)(=O)[O-].[Na+].[Na+] Chemical compound C1=CC=C(C=C1)CC(=S)OCC(F)(F)S(=O)(=O)[O-].C1=CC=C(C=C1)CC(=S)OCC(F)(F)S(=O)(=O)[O-].[Na+].[Na+] SBZKKRAVIDMFNA-UHFFFAOYSA-L 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 2
- ZLWCHADTVXUSGT-UHFFFAOYSA-M sodium;1,1-difluoro-2-(4-phenylbenzoyl)oxyethanesulfonate Chemical compound [Na+].C1=CC(C(=O)OCC(F)(F)S(=O)(=O)[O-])=CC=C1C1=CC=CC=C1 ZLWCHADTVXUSGT-UHFFFAOYSA-M 0.000 description 2
- UMQRPAAGHVZTPN-UHFFFAOYSA-M sodium;2-benzoyloxy-1,1-difluoroethanesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C(F)(F)COC(=O)C1=CC=CC=C1 UMQRPAAGHVZTPN-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical class SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 description 1
- KQPQZWKCUWVZDD-UHFFFAOYSA-N 1-methyladamantane;prop-2-enoic acid Chemical compound OC(=O)C=C.C1C(C2)CC3CC2CC1(C)C3 KQPQZWKCUWVZDD-UHFFFAOYSA-N 0.000 description 1
- 125000001088 1-naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- CXJOONIFSVSFAD-UHFFFAOYSA-N 2-(4-methoxyphenyl)acetyl chloride Chemical compound COC1=CC=C(CC(Cl)=O)C=C1 CXJOONIFSVSFAD-UHFFFAOYSA-N 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- PKUPAJQAJXVUEK-UHFFFAOYSA-N 2-phenoxyacetyl chloride Chemical compound ClC(=O)COC1=CC=CC=C1 PKUPAJQAJXVUEK-UHFFFAOYSA-N 0.000 description 1
- VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 1
- UJXIOVIFPTXDHU-UHFFFAOYSA-N 2-phenylethanethioyl chloride Chemical compound ClC(=S)CC1=CC=CC=C1 UJXIOVIFPTXDHU-UHFFFAOYSA-N 0.000 description 1
- SYVNVEGIRVXRQH-UHFFFAOYSA-N 3-fluorobenzoyl chloride Chemical compound FC1=CC=CC(C(Cl)=O)=C1 SYVNVEGIRVXRQH-UHFFFAOYSA-N 0.000 description 1
- JPVUWCPKMYXOKW-UHFFFAOYSA-N 4-phenylbenzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1C1=CC=CC=C1 JPVUWCPKMYXOKW-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- JLXRKFLFNCCVDT-UHFFFAOYSA-N C1(=CC=CC=C1)C(C1=CC=CC=C1)[SH+]C1=CC=CC=C1.FC(COC(C1=CC=CC=C1)=O)(S(=O)(=O)[O-])F Chemical compound C1(=CC=CC=C1)C(C1=CC=CC=C1)[SH+]C1=CC=CC=C1.FC(COC(C1=CC=CC=C1)=O)(S(=O)(=O)[O-])F JLXRKFLFNCCVDT-UHFFFAOYSA-N 0.000 description 1
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- RDUDSYPOHRDGTE-UHFFFAOYSA-N CS(C)(CC(OCCS(O)(=O)=O)=O)C1=CC=CCC1 Chemical compound CS(C)(CC(OCCS(O)(=O)=O)=O)C1=CC=CCC1 RDUDSYPOHRDGTE-UHFFFAOYSA-N 0.000 description 1
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- 101150065749 Churc1 gene Proteins 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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- DXCUUSGHVXLQGF-UHFFFAOYSA-N OS(CCOC(COc1ccccc1)=O)(=O)=O Chemical compound OS(CCOC(COc1ccccc1)=O)(=O)=O DXCUUSGHVXLQGF-UHFFFAOYSA-N 0.000 description 1
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- YBVRUEQLVWXBOU-UHFFFAOYSA-M [Na+].C(C)OC(C(S(=O)(=O)[O-])(F)F)=O Chemical compound [Na+].C(C)OC(C(S(=O)(=O)[O-])(F)F)=O YBVRUEQLVWXBOU-UHFFFAOYSA-M 0.000 description 1
- NUWRDVWBVNBAHB-UHFFFAOYSA-M [Na+].FC(COC(C1=C(C=CC=C1)F)=O)(S(=O)(=O)[O-])F Chemical compound [Na+].FC(COC(C1=C(C=CC=C1)F)=O)(S(=O)(=O)[O-])F NUWRDVWBVNBAHB-UHFFFAOYSA-M 0.000 description 1
- VQHVDVCUPVXZKH-UHFFFAOYSA-L [Na+].O(C1=CC=CC=C1)CC(=O)OCC(S(=O)(=O)[O-])(F)F.[Na+].O(C1=CC=CC=C1)CC(=O)OCC(S(=O)(=O)[O-])(F)F Chemical compound [Na+].O(C1=CC=CC=C1)CC(=O)OCC(S(=O)(=O)[O-])(F)F.[Na+].O(C1=CC=CC=C1)CC(=O)OCC(S(=O)(=O)[O-])(F)F VQHVDVCUPVXZKH-UHFFFAOYSA-L 0.000 description 1
- RWYBZZFLHYELEI-UHFFFAOYSA-L [Na+].[Na+].C1(=CC=CC=C1)CC(=O)OCC(S(=O)(=O)[O-])(F)F.C1(=CC=CC=C1)CC(=O)OCC(S(=O)(=O)[O-])(F)F Chemical compound [Na+].[Na+].C1(=CC=CC=C1)CC(=O)OCC(S(=O)(=O)[O-])(F)F.C1(=CC=CC=C1)CC(=O)OCC(S(=O)(=O)[O-])(F)F RWYBZZFLHYELEI-UHFFFAOYSA-L 0.000 description 1
- SOBZJAKZEDEMCC-UHFFFAOYSA-L [Na+].[Na+].C1=CC=CC2=CC3=CC=CC=C3C(=C12)C(=O)OCC(S(=O)(=O)[O-])(F)F.C1=CC=CC2=CC3=CC=CC=C3C(=C12)C(=O)OCC(S(=O)(=O)[O-])(F)F Chemical compound [Na+].[Na+].C1=CC=CC2=CC3=CC=CC=C3C(=C12)C(=O)OCC(S(=O)(=O)[O-])(F)F.C1=CC=CC2=CC3=CC=CC=C3C(=C12)C(=O)OCC(S(=O)(=O)[O-])(F)F SOBZJAKZEDEMCC-UHFFFAOYSA-L 0.000 description 1
- KBZOQLICEGAQAQ-UHFFFAOYSA-L [Na+].[Na+].COC1=CC=C(C=C1)CC(=O)OCC(S(=O)(=O)[O-])(F)F.COC1=CC=C(C=C1)CC(=O)OCC(S(=O)(=O)[O-])(F)F Chemical compound [Na+].[Na+].COC1=CC=C(C=C1)CC(=O)OCC(S(=O)(=O)[O-])(F)F.COC1=CC=C(C=C1)CC(=O)OCC(S(=O)(=O)[O-])(F)F KBZOQLICEGAQAQ-UHFFFAOYSA-L 0.000 description 1
- XQVRPMOKIVUPOC-UHFFFAOYSA-N [Na].FC(S(=O)(=O)[O-])(F)F.C(CCC)OC(=O)CO[SH+]C1=CC=CC=C1 Chemical compound [Na].FC(S(=O)(=O)[O-])(F)F.C(CCC)OC(=O)CO[SH+]C1=CC=CC=C1 XQVRPMOKIVUPOC-UHFFFAOYSA-N 0.000 description 1
- IMCDIEYHPUJLQS-UHFFFAOYSA-N [Na].FC(S(=O)(=O)[O-])(F)F.C1(=CC=CC=C1)C=1C(=C(C=CC1)[SH+]F)C1=CC=CC=C1 Chemical compound [Na].FC(S(=O)(=O)[O-])(F)F.C1(=CC=CC=C1)C=1C(=C(C=CC1)[SH+]F)C1=CC=CC=C1 IMCDIEYHPUJLQS-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- JIMXXGFJRDUSRO-UHFFFAOYSA-N adamantane-1-carboxylic acid Chemical compound C1C(C2)CC3CC2CC1(C(=O)O)C3 JIMXXGFJRDUSRO-UHFFFAOYSA-N 0.000 description 1
- 125000005577 anthracene group Chemical group 0.000 description 1
- REJFOBQJXSGDSB-UHFFFAOYSA-N anthracene-9-carbonyl chloride Chemical compound C1=CC=C2C(C(=O)Cl)=C(C=CC=C3)C3=CC2=C1 REJFOBQJXSGDSB-UHFFFAOYSA-N 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- UDDVOWOZYSGUMO-UHFFFAOYSA-N benzhydrylsulfanylbenzene;1,1-difluoro-2-(2-phenylacetyl)oxyethanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)COC(=O)CC1=CC=CC=C1.C=1C=CC=CC=1SC(C=1C=CC=CC=1)C1=CC=CC=C1 UDDVOWOZYSGUMO-UHFFFAOYSA-N 0.000 description 1
- GIMIGUAZJNQDOB-UHFFFAOYSA-N benzhydrylsulfanylbenzene;1,1-difluoro-2-(3-fluorobenzoyl)oxyethanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)COC(=O)C1=CC=CC(F)=C1.C=1C=CC=CC=1SC(C=1C=CC=CC=1)C1=CC=CC=C1 GIMIGUAZJNQDOB-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000001459 lithography Methods 0.000 description 1
- ULWOJODHECIZAU-UHFFFAOYSA-N n,n-diethylpropan-2-amine Chemical compound CCN(CC)C(C)C ULWOJODHECIZAU-UHFFFAOYSA-N 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- LLXPAAYVGWUQLU-UHFFFAOYSA-M sodium;1,1-difluoro-2-(2-phenoxyacetyl)oxyethanesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C(F)(F)COC(=O)COC1=CC=CC=C1 LLXPAAYVGWUQLU-UHFFFAOYSA-M 0.000 description 1
- CAKIMBSUMXYOGF-UHFFFAOYSA-M sodium;1,1-difluoro-2-(2-phenylacetyl)oxyethanesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C(F)(F)COC(=O)CC1=CC=CC=C1 CAKIMBSUMXYOGF-UHFFFAOYSA-M 0.000 description 1
- NMSCYHMTZUKKRP-UHFFFAOYSA-M sodium;1,1-difluoro-2-[2-(4-methoxyphenyl)acetyl]oxyethanesulfonate Chemical compound [Na+].COC1=CC=C(CC(=O)OCC(F)(F)S([O-])(=O)=O)C=C1 NMSCYHMTZUKKRP-UHFFFAOYSA-M 0.000 description 1
- NJODVFGGCRPLAX-UHFFFAOYSA-M sodium;2-(anthracene-9-carbonyloxy)-1,1-difluoroethanesulfonate Chemical compound [Na+].C1=CC=C2C(C(=O)OCC(F)(F)S(=O)(=O)[O-])=C(C=CC=C3)C3=CC2=C1 NJODVFGGCRPLAX-UHFFFAOYSA-M 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical class CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 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
- 238000001291 vacuum drying Methods 0.000 description 1
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- C07C309/20—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic unsaturated carbon skeleton
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- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/07—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton
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- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/52—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
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Description
前記式において、ZはOSO2CF3、OSO2C4F9、OSO2C8F17、N(CF3)2、N(C2F5)2、N(C4F9)2、C(CF3)3、C(C2F5)3、C(C4F9)3、F、Cl、Br、I、BF4、ASF6またはPF6であり、A+は有機対イオンである。
安息香酸−2,2−ジフルオロ−2−スルホ−エチルエステルジフェニルメチルフェニルスルホニウム塩(Benzoic acid−2,2−difluoro−2−sulfo−ethyl ester diphenyl methylphenyl sulfonium salt)
<1>氷浴中でジフルオロスルホ酢酸エチルエステルナトリウム塩(difluoro sulfo acetic acid ethyl ester sodium salt)83gをメタノール160ml及び1.2LのTHFに溶かし、水素化ホウ素ナトリウム(NaBH4)44gをゆっくり滴加した。滴加が完了した後に氷浴を除去し、昇温して60℃で約4時間撹拌した。
1H−NMR(D2O):d(ppm)4.18(t,2H)
<1>[合成例1]の<1>で製造したジフルオロヒドロキシエタンスルホン酸ナトリウム塩(difluoro hydroxyl ethane sulfonic acid sodium salt)10gと3−フルオロベンゾイルクロライド12.8gをジクロロエタン150mlに溶かして常温で撹拌した。トリエチルアミン15.05mlを常温で徐々に滴加した後、反応温度を60℃にまで昇温して2時間撹拌した。
<1>前記合成例1の<2>とは全ての反応条件を同一にするが、アルコールとの反応物としてベンゾイルクロライドの代わりにフェニルアセチルクロライド(10.8)mlを用いて、下記のようなフェニルアセチルオキシメチルジフルオロメタンスルホン酸ナトリウムナトリウム塩7.6g(収率46.6%)を収得し、その構造を1H NMRによって確認した(図5参照)。
<1>合成例1の<2>とは全ての反応条件を同一にするが、アルコールとの反応物としてベンゾイルクロライドの代わりに4−メトキシフェニルアセチルクロライド10gを用いて、下記反応式8のような4−メトキシフェニルアセチルオキシメチルジフルオロメタンスルホン酸ナトリウムナトリウム塩7.1g(収率59.4%)を収得し、その構造を1H NMRによって確認した(図7参照)。
<1>合成例1の<2>とは全ての反応条件を同一にするが、アルコールとの反応物としてベンゾイルクロライドの代わりにフェノキシアセチルクロライド8.98mlを用いて、下記反応式10のようなフェノキシアセチルオキシメチルジフルオロメタンスルホン酸ナトリウムナトリウム塩10g(収率87.7%)を収得し、その構造を1H NMRによって確認した(図9参照)。
<1>合成例1の<2>とは全ての反応条件を同一にするが、アルコールとの反応物としてベンゾイルクロライドの代わりにフェニルチオアセチルクロライド10.6gを用いて、下記反応式12のようなフェニルチオアセチルオキシメチルジフルオロメタンスルホン酸ナトリウムナトリウム塩6.87g(収率54.1%)を収得し、その構造を1H NMRによって確認した(図11参照)。
<1>合成例1の<2>とは全ての反応条件を同一にするが、アルコールとの反応物としてベンゾイルクロライドの代わりに1−ナフトニルクロライド12.2mlを用いて、下記反応式14のような1−ナフトニルオキシメチルジフルオロメタンスルホン酸ナトリウムナトリウム塩17g(収率93%)を収得し、その構造を1H NMRによって確認した(図13参照)。
<1>合成例1の<2>とは全ての反応条件を同一にするが、アルコールとの反応物としてベンゾイルクロライドの代わりに4−フェニルベンゾイルクロライド17.7mlを用いて、下記反応式16のような4−フェニルベンゾイルオキシメチルジフルオロメタンスルホン酸ナトリウムナトリウム塩16g(収率95.8%)を収得し、その構造を1H NMRによって確認した(図15参照)。
<1>合成例1の<2>とは全ての反応条件を同一にするが、アルコールとの反応物としてベンゾイルクロライドの代わりに9−アントラセンカルボニルクロライド19.6gを用いて、下記反応式18のような9−アントラセンカルボニルオキシメチルジフルオロメタンスルホン酸ナトリウムナトリウム塩21g(収率99%)を収得し、その構造を1H NMRによって確認した。
<1>合成例1の<2>で製造した安息香酸−2,2−ジフルオロ−2−スルホ−エチルエステルナトリウム塩(Benzoic acid 2,2−difluoro−2−sulfoethyl ester sodium salt)7gとジフェニルt−ブトキシカルボニルメトキシフェニルスルホニウムトリフルオロメタンスルホン酸ナトリウム塩7gをジクロロメタン70ml、水70mlに溶かし、二層反応をして3時間激しく撹拌した。
<1>合成例1の<2>で製造した安息香酸−2,2−ジフルオロ−2−スルホ−エチルエステルナトリウム塩(Benzoic acid−2,2−difluoro−2−sulfo−ethyl ester sodium salt)8.9gとジフェニルフルオロフェニルスルホニウムトリフルオロメタンスルホン酸ナトリウム塩7gをジクロロメタン70ml、水70mlに溶かし、二層反応をして3時間激しく撹拌した。
3−ビシクロ[2.2.1]ヘプト−5−エン−2−イル−3−ヒドロキシプロピオン酸t−ブチルエステル(3−Bicyclo[2.2.1]hept−5−en−2−yl−3−hydroxy−propionic acid t−butyl ester、以下、BHPという)、1−メチルアダマンタンアクリレート(1−methyl adamantane acrylate)、γ−ブチロラクトンメチルアクリレート(γ−butyrolactone methyl acrylate)を1:1:1(33部:33部:33部)のモル比で充填し、重合溶媒としては1,4−ジオキサンを反応単量体総質量の3倍用い、開始剤としてはアゾビスイソブチロニトリルを単量体総モル量を基準に4mol%の比率で用いて、65℃で16時間反応させた。
実施例1:レジストの調製
樹脂合成例1で得られた樹脂100質量部に対し、酸発生剤として合成例1で作られたアダマンタン−1−カルボン酸−2,2−ジフルオロ−2−スルホ−エチルエステルジフェニルメチルフェニルスルホニウム塩4質量部と、塩基性添加剤としてテトラメチルアンモニウムヒドロキシド0.5質量部を、プロピレングリコールメチルエーテルアセテート1,000質量部に溶解した後、0.2μm膜フィルタで濾過してレジストを調製した。
合成例1の<3>、2の<2>、3の<2>から得られたPAGを用い、前記樹脂合成例1で作られた樹脂、塩基性添加剤をプロピレングリコールメチルエーテルアセテート1,000質量部に溶解した後、0.2μm膜フィルタで濾過し、表1に表されるレジスト組成物(但し、「部」は質量基準である)を調製した後、実施例1と同様に実施してポジティブレジストパターンを形成した後に各種評価を行った。評価結果は表1に示す
実施例1:合成例1の<3>の、安息香酸−2,2−ジフルオロ−2−スルホ−エチル−エステルジフェニルフルオロフェニルスルホニウム塩(Benzoic acid−2,2−difluoro−2−sulfo−ethyl ester diphenyl fluorophenyl sulfonium salt)
実施例2:合成例2の<2>の、3−フルオロ安息香酸2,2−ジフルオロ−2−スルホ−エチル−エステルジフェニルメチルフェニルスルホニウム塩(3−fluoro benzoic acid−2,2−difluoro−2−sulfur−ethyl−ester diphenylmethylphenyl sulfonium salts)
実施例3:合成例3の<2>の、フェニル酢酸2,2−ジフルオロ−2−スルホ−エチル−エステルジフェニルメチルフェニルスルホニウム塩(Phenyl acetic acid−2,2−difluoro−2−sulfur ethyl ester diphenylmethylphenyl sulfonium salt)
比較例1:トリフェニルスルホニウムトリフレート
光酸発生剤のアニオンに芳香族環を導入して製造した本発明の物質は、既存のトリフレートやノナフレートの光酸発生剤に比べ、トリフレートと類似する酸度を維持し、酸の拡散速度が遅く、拡散距離が短くて、益々微細化するL/Sのパターン実現に適した特性を有し、前記表に見られるように、LERと解像度の側面で既存のトリフレートタイプより遥かに良い性能を示すことが分かる。アニオンへの芳香族の導入は、光を照射する時に透明度に特に問題を起こさず、一旦、酸が発生してアニオンの形態に移動するときには、芳香族環は透明度にいかなる影響も与えずに芳香族の大きさに応じて酸の拡散速度と拡散距離を調節できる利点があり、既存の光酸発生剤とは区別される特徴を示した。
Claims (15)
- 下記化学式1、1−xiv〜1−xx、1−xxii、1−xxxviii、1−xxxxv、1−xxxxi、1−xxxxx、1−xxxxxiで表される化合物群から選択されるいずれかひとつの光酸発生剤:
前記式において、Xは炭素数1〜10のアルキレン、−X1−O−X2−、またはN、あるいは、Sであり、前記X1およびX2は各々独立に炭素数1〜10のアルキレンであり、Yは1つ以上の芳香族環を含む炭素数5〜30の炭化水素環基であり、前記炭化水素環基の環状の1つ以上の水素原子が−O−Y1、−CO−Y2、炭素数1〜6のアルキル基、炭素数1〜6のアルコキシ基、炭素数1〜4のペルフルオロアルキル基、炭素数1〜4のペルフルオロアルコキシ基、炭素数1〜6のヒドロキシアルキル基、ハロゲン原子、ヒドロキシル基およびシアノ基からなる群から選択された1つ以上で置換されてもよく、前記Y1およびY2は各々独立に炭素数1〜6のアルキル基であり、nは0または1であり、A+は有機対イオンである。
- 前記Yはフェニル基、ナフチル基、アントリル基、フェナントレン基、フルオレニル基またはピレン基であり、これらの環状の1つ以上の水素原子は−O−Y1、−CO−Y2、炭素数1〜6のアルキル基、炭素数1〜6のアルコキシ基、炭素数1〜4のペルフルオロアルキル基、炭素数1〜4のペルフルオロアルコキシ基、炭素数1〜6のヒドロキシアルキル基、ハロゲン原子、ヒドロキシル基およびシアノ基からなる群から選択された1つ以上で置換されてもよく、前記Y1およびY2は各々独立に炭素数1〜6のアルキル基である請求項1に記載の光酸発生剤。
- 前記酸発生剤は下記化学式4a、化学式4b、化学式4cまたは化学式4dである請求項1に記載の光酸発生剤:
前記式において、R10、R11およびR15は各々独立に炭素数1〜12のアルキル基、炭素数2〜12のアリル基、炭素数1〜12のペルフルオロアルキル基、ベンジル基、または炭素数5〜20のアリール基であり、R12、R13、R14、R16、R17およびR18は各々独立に水素、炭素数1〜12のアルキル基、ハロゲン原子、炭素数1〜12のアルコキシ基、炭素数5〜20のアリール基、チオフェノキシ基、炭素数1〜12のチオアルコキシ基または炭素数1〜6のアルコキシカルボニルメトキシ基であり、Bは下記化学式5〜化学式13のうちのいずれか1つを表す。
- 前記化学式1の化合物は下記化学式14の塩と化学式15で表される化合物の反応によって製造される請求項1に記載の光酸発生剤:
前記式において、Xは炭素数1〜10のアルキレン、−X1−O−X2−またはN、あるいは、Sであり、前記X1およびX2は各々独立に炭素数1〜10のアルキレンであり、Yは1つ以上の芳香族環を含む炭素数5〜30の炭化水素環基であり、前記炭化水素環基の環状の1つ以上の水素原子が−O−Y1、−CO−Y2、炭素数1〜6のアルキル基、炭素数1〜6のアルコキシ基、炭素数1〜4のペルフルオロアルキル基、炭素数1〜4のペルフルオロアルコキシ基、炭素数1〜6のヒドロキシアルキル基、ハロゲン原子、ヒドロキシル基およびシアノ基からなる群から選択された1つ以上で置換されてもよく、前記Y1およびY2は各々独立に炭素数1〜6のアルキル基であり、MはLi、NaまたはKであり、nは0または1である;
前記式において、ZはOSO2CF3、OSO2C4F9、OSO2C8F17、N(CF3)2、N(C2F5)2、N(C4F9)2、C(CF3)3、C(C2F5)3、C(C4F9)3、F、Cl、Br、I、BF4、ASF6またはPF6であり、A+は有機対イオンである。 - 前記化学式14の塩は下記化学式16のアルコール化合物と化学式17のカルボニルクロライド化合物を反応させて製造する請求項10に記載の光酸発生剤。
前記式において、MはLi、NaまたはKである;
前記式において、Xは炭素数3〜30の一環式または多環式炭化水素基であり、前記一環式または多環式炭化水素基のうちの少なくとも1つ以上の水素がエーテル基、エステル基、カルボニル基、アセタール基、エポキシ基、ニトリル基またはアルデヒド基を含むかあるいは含まない炭素数1〜10のアルキルまたはアルコキシ基、炭素数1〜4のペルフルオロアルキル基、炭素数1〜10のヒドロキシアルキル基またはシアノ基で置換されてもよく、前記Yはフェニル基、ナフチル基、アントリル基、フェナントレン基、フルオレニル基またはピレン基であり、これらの環状の1つ以上の水素原子は−O−Y1、−CO−Y2、炭素数1〜6のアルキル基、炭素数1〜6のアルコキシ基、炭素数1〜4のペルフルオロアルキル基、炭素数1〜4のペルフルオロアルコキシ基、炭素数1〜6のヒドロキシアルキル基、ハロゲン原子、ヒドロキシル基およびシアノ基からなる群から選択された1つ以上で置換されてもよく、前記Y1およびY2は各々独立に炭素数1〜6のアルキル基である。 - 前記還元剤は、水素化ホウ素ナトリウム、水素化アルミニウムリチウム(LiAlH4)、BH3−THF、NaBH4−AlCl3、NaBH4−LiCl、LiAl(OMe)3からなる群から選択された1つ以上である請求項12に記載の光酸発生剤。
- 下記化学式14で表される化合物:
前記式において、Xは炭素数1〜10のアルキレン、−X1−O−X2−またはN、あるいは、Sであり、前記X1およびX2は各々独立に炭素数1〜10のアルキレンであり、Yは1つ以上の芳香族環を含む炭素数5〜30の炭化水素環基であり、前記炭化水素環基の環状の1つ以上の水素原子が−O−Y1、−CO−Y2、炭素数1〜6のアルキル基、炭素数1〜6のアルコキシ基、炭素数1〜4のペルフルオロアルキル基、炭素数1〜4のペルフルオロアルコキシ基、炭素数1〜6のヒドロキシアルキル基、ハロゲン原子、ヒドロキシル基およびシアノ基からなる群から選択された1つ以上で置換されてもよく、前記Y1およびY2は各々独立に炭素数1〜6のアルキル基であり、MはLi、NaまたはKであり、nは0または1である。 - 請求項1に記載の光酸発生剤を含む化学増幅型レジスト組成物。
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US8435717B2 (en) * | 2007-02-15 | 2013-05-07 | Central Glass Company, Limited | Compound for photoacid generator, resist composition using the same, and pattern-forming method |
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2008
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2009
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- 2009-04-20 JP JP2009101787A patent/JP5149236B2/ja active Active
- 2009-09-03 TW TW098129709A patent/TWI421236B/zh active
- 2009-09-15 SG SG200906123-5A patent/SG161145A1/en unknown
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Cited By (7)
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KR20180002048A (ko) | 2016-06-28 | 2018-01-05 | 도오꾜오까고오교 가부시끼가이샤 | 레지스트 조성물 및 레지스트 패턴 형성 방법 |
US10241406B2 (en) | 2016-06-28 | 2019-03-26 | Tokyo Ohka Kogyo Co., Ltd. | Resist composition and method for forming resist pattern |
US11703756B2 (en) | 2018-05-28 | 2023-07-18 | Tokyo Ohka Kogyo Co., Ltd. | Resist composition and method of forming resist pattern |
US11709425B2 (en) | 2018-05-28 | 2023-07-25 | Tokyo Ohka Kogyo Co., Ltd. | Resist composition and method of forming resist pattern |
US11029600B2 (en) | 2018-09-07 | 2021-06-08 | Tokyo Ohka Kogyo Co., Ltd. | Resist composition and method of forming resist pattern |
US11460770B2 (en) | 2018-12-04 | 2022-10-04 | Tokyo Ohka Kogyo Co., Ltd. | Resist composition, method of forming resist pattern, and compound |
US11635686B2 (en) | 2018-12-04 | 2023-04-25 | Tokyo Ohka Kogyo Co., Ltd. | Resist composition, method of forming resist pattern, and compound |
Also Published As
Publication number | Publication date |
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CN101727004A (zh) | 2010-06-09 |
KR20100048047A (ko) | 2010-05-11 |
TW201016649A (en) | 2010-05-01 |
TWI421236B (zh) | 2014-01-01 |
JP2010106236A (ja) | 2010-05-13 |
US20100113818A1 (en) | 2010-05-06 |
SG161145A1 (en) | 2010-05-27 |
CN101727004B (zh) | 2013-05-22 |
US8026390B2 (en) | 2011-09-27 |
KR100998503B1 (ko) | 2010-12-07 |
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