JP3975411B2 - オキシムスルホン酸エステルおよび潜伏性スルホン酸としてのそれらの使用 - Google Patents
オキシムスルホン酸エステルおよび潜伏性スルホン酸としてのそれらの使用 Download PDFInfo
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- JP3975411B2 JP3975411B2 JP30583496A JP30583496A JP3975411B2 JP 3975411 B2 JP3975411 B2 JP 3975411B2 JP 30583496 A JP30583496 A JP 30583496A JP 30583496 A JP30583496 A JP 30583496A JP 3975411 B2 JP3975411 B2 JP 3975411B2
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- phenyl
- unsubstituted
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- -1 Oxime sulfonate esters Chemical class 0.000 title claims abstract description 176
- 150000003460 sulfonic acids Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 77
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 73
- 239000002253 acid Substances 0.000 claims abstract description 64
- 229920002120 photoresistant polymer Polymers 0.000 claims abstract description 35
- 125000005561 phenanthryl group Chemical group 0.000 claims abstract description 24
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 13
- 238000004519 manufacturing process Methods 0.000 claims abstract description 13
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 13
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 228
- 239000000203 mixture Substances 0.000 claims description 85
- 125000000217 alkyl group Chemical group 0.000 claims description 79
- 125000001424 substituent group Chemical group 0.000 claims description 49
- 230000005855 radiation Effects 0.000 claims description 34
- 239000000463 material Substances 0.000 claims description 27
- 125000002252 acyl group Chemical group 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 25
- 125000001188 haloalkyl group Chemical group 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims description 22
- 125000001624 naphthyl group Chemical group 0.000 claims description 22
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 20
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 19
- 238000004132 cross linking Methods 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 14
- 150000007513 acids Chemical class 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- IFVTZJHWGZSXFD-UHFFFAOYSA-N biphenylene Chemical group C1=CC=C2C3=CC=CC=C3C2=C1 IFVTZJHWGZSXFD-UHFFFAOYSA-N 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000004957 naphthylene group Chemical group 0.000 claims description 12
- 125000002947 alkylene group Chemical group 0.000 claims description 11
- 239000003973 paint Substances 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 230000009471 action Effects 0.000 claims description 10
- 239000003112 inhibitor Substances 0.000 claims description 10
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- 125000005605 benzo group Chemical group 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 238000007639 printing Methods 0.000 claims description 7
- 238000004090 dissolution Methods 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 6
- 125000005146 naphthylsulfonyl group Chemical group C1(=CC=CC2=CC=CC=C12)S(=O)(=O)* 0.000 claims description 6
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 6
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 6
- 230000001678 irradiating effect Effects 0.000 claims description 4
- 150000001721 carbon Chemical group 0.000 claims description 3
- 239000000976 ink Substances 0.000 claims description 3
- 125000006091 1,3-dioxolane group Chemical group 0.000 claims description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 3
- 206010034972 Photosensitivity reaction Diseases 0.000 claims 1
- 230000036211 photosensitivity Effects 0.000 claims 1
- 239000004575 stone Substances 0.000 claims 1
- 150000002148 esters Chemical class 0.000 abstract description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 78
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 75
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 57
- 238000000576 coating method Methods 0.000 description 44
- 239000000243 solution Substances 0.000 description 40
- 239000011248 coating agent Substances 0.000 description 36
- 238000006243 chemical reaction Methods 0.000 description 34
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- 239000012043 crude product Substances 0.000 description 25
- 229920005989 resin Polymers 0.000 description 25
- 239000011347 resin Substances 0.000 description 25
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- 238000000921 elemental analysis Methods 0.000 description 24
- 238000002844 melting Methods 0.000 description 23
- 230000008018 melting Effects 0.000 description 23
- 238000010521 absorption reaction Methods 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 229920000642 polymer Polymers 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 239000011230 binding agent Substances 0.000 description 17
- 239000007787 solid Substances 0.000 description 17
- 238000002211 ultraviolet spectrum Methods 0.000 description 17
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- 239000013078 crystal Substances 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 238000001723 curing Methods 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 238000011161 development Methods 0.000 description 13
- 238000005160 1H NMR spectroscopy Methods 0.000 description 12
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 12
- 238000001953 recrystallisation Methods 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- 239000003921 oil Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- OHZRRBNQINJVRP-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-2-hydroxyiminoacetonitrile Chemical compound COC1=CC=C(C(=NO)C#N)C=C1OC OHZRRBNQINJVRP-UHFFFAOYSA-N 0.000 description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 9
- 229920000877 Melamine resin Polymers 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- BZOYSERZNRJPDQ-UHFFFAOYSA-N [(3,6-dimethoxyfluoren-9-ylidene)amino] 4-methylbenzenesulfonate Chemical compound C12=CC=C(OC)C=C2C2=CC(OC)=CC=C2C1=NOS(=O)(=O)C1=CC=C(C)C=C1 BZOYSERZNRJPDQ-UHFFFAOYSA-N 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 239000003480 eluent Substances 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 8
- 229920001225 polyester resin Polymers 0.000 description 8
- 239000004645 polyester resin Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 8
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 7
- UJNAXQMROWKSIE-UHFFFAOYSA-N 3,6-dimethoxyfluoren-9-one Chemical compound C1=C(OC)C=C2C3=CC(OC)=CC=C3C(=O)C2=C1 UJNAXQMROWKSIE-UHFFFAOYSA-N 0.000 description 7
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 description 7
- 239000004925 Acrylic resin Substances 0.000 description 7
- 229920000178 Acrylic resin Polymers 0.000 description 7
- ZSDOTLZPCSTZIQ-UHFFFAOYSA-N OCCSC1=CC=CC2=C1C1=CC=CC=C1C2 Chemical compound OCCSC1=CC=CC2=C1C1=CC=CC=C1C2 ZSDOTLZPCSTZIQ-UHFFFAOYSA-N 0.000 description 7
- 239000003377 acid catalyst Substances 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- ODCCUFNTRJQXHK-UHFFFAOYSA-N n-(3,6-dimethoxyfluoren-9-ylidene)hydroxylamine Chemical compound C1=C(OC)C=C2C3=CC(OC)=CC=C3C(=NO)C2=C1 ODCCUFNTRJQXHK-UHFFFAOYSA-N 0.000 description 7
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- 125000006239 protecting group Chemical group 0.000 description 7
- 230000035945 sensitivity Effects 0.000 description 7
- UUBKTKYSBIWUFZ-UHFFFAOYSA-N 2-hydroxyimino-2-(4-methylsulfanylphenyl)acetonitrile Chemical compound CSC1=CC=C(C(=NO)C#N)C=C1 UUBKTKYSBIWUFZ-UHFFFAOYSA-N 0.000 description 6
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
- SWRRBALMTWBXKJ-UHFFFAOYSA-N [(3,6-dimethoxyfluoren-9-ylidene)amino] 4-dodecylbenzenesulfonate Chemical compound C1=CC(CCCCCCCCCCCC)=CC=C1S(=O)(=O)ON=C1C2=CC=C(OC)C=C2C2=CC(OC)=CC=C21 SWRRBALMTWBXKJ-UHFFFAOYSA-N 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000004922 lacquer Substances 0.000 description 6
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-methyl-PhOH Natural products CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 6
- 230000007246 mechanism Effects 0.000 description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 6
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-methyl phenol Natural products CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 6
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
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- YEXOWHQZWLCHHD-UHFFFAOYSA-N 3,5-ditert-butyl-4-hydroxybenzoic acid Chemical compound CC(C)(C)C1=CC(C(O)=O)=CC(C(C)(C)C)=C1O YEXOWHQZWLCHHD-UHFFFAOYSA-N 0.000 description 4
- JAGRUUPXPPLSRX-UHFFFAOYSA-N 4-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=C(O)C=C1 JAGRUUPXPPLSRX-UHFFFAOYSA-N 0.000 description 4
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- PLBYSHJEOLBAIR-UHFFFAOYSA-N [(1,6-dimethoxyfluoren-9-ylidene)amino] 4-methylbenzenesulfonate Chemical compound C1=CC=C(OC)C2=C1C1=CC(OC)=CC=C1C2=NOS(=O)(=O)C1=CC=C(C)C=C1 PLBYSHJEOLBAIR-UHFFFAOYSA-N 0.000 description 4
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- 150000003863 ammonium salts Chemical class 0.000 description 4
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- 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 4
- 239000003054 catalyst Substances 0.000 description 4
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 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 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 4
- WCYJQVALWQMJGE-UHFFFAOYSA-M hydroxylammonium chloride Chemical compound [Cl-].O[NH3+] WCYJQVALWQMJGE-UHFFFAOYSA-M 0.000 description 4
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- 229910052751 metal Inorganic materials 0.000 description 4
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- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 4
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- GQRXDRJNCURJKY-UHFFFAOYSA-N 1,6-dimethoxyfluoren-9-one Chemical compound C12=CC(OC)=CC=C2C(=O)C2=C1C=CC=C2OC GQRXDRJNCURJKY-UHFFFAOYSA-N 0.000 description 3
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
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- VBHIRACIRQVMMY-UHFFFAOYSA-N [(1,6-dimethoxyfluoren-9-ylidene)amino] 4-dodecylbenzenesulfonate Chemical compound C1=CC(CCCCCCCCCCCC)=CC=C1S(=O)(=O)ON=C1C2=C(OC)C=CC=C2C2=CC(OC)=CC=C21 VBHIRACIRQVMMY-UHFFFAOYSA-N 0.000 description 3
- MTEBYNMPDCHMFF-UHFFFAOYSA-N [(3,6-dimethoxyfluoren-9-ylidene)amino] octane-1-sulfonate Chemical compound COC1=CC=C2C(=NOS(=O)(=O)CCCCCCCC)C3=CC=C(OC)C=C3C2=C1 MTEBYNMPDCHMFF-UHFFFAOYSA-N 0.000 description 3
- FYBZEMOLLYRPDG-UHFFFAOYSA-N [[cyano-(3,4-dimethoxyphenyl)methylidene]amino] 2,4,6-tri(propan-2-yl)benzenesulfonate Chemical compound C1=C(OC)C(OC)=CC=C1C(C#N)=NOS(=O)(=O)C1=C(C(C)C)C=C(C(C)C)C=C1C(C)C FYBZEMOLLYRPDG-UHFFFAOYSA-N 0.000 description 3
- DDQUYNFKTKRRKM-UHFFFAOYSA-N [[cyano-(3,4-dimethoxyphenyl)methylidene]amino] 4-chlorobenzenesulfonate Chemical compound C1=C(OC)C(OC)=CC=C1C(C#N)=NOS(=O)(=O)C1=CC=C(Cl)C=C1 DDQUYNFKTKRRKM-UHFFFAOYSA-N 0.000 description 3
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- 238000004528 spin coating Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- NZNAAUDJKMURFU-UHFFFAOYSA-N tetrakis(2,2,6,6-tetramethylpiperidin-4-yl) butane-1,2,3,4-tetracarboxylate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CC(C(=O)OC1CC(C)(C)NC(C)(C)C1)C(C(=O)OC1CC(C)(C)NC(C)(C)C1)CC(=O)OC1CC(C)(C)NC(C)(C)C1 NZNAAUDJKMURFU-UHFFFAOYSA-N 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 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
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- AYNNSCRYTDRFCP-UHFFFAOYSA-N triazene Chemical compound NN=N AYNNSCRYTDRFCP-UHFFFAOYSA-N 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 125000002948 undecyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 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
- 150000003739 xylenols Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
- C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
- C07C309/66—Methanesulfonates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/73—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/75—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing singly-bound oxygen atoms bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- 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
- C07C323/62—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 atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/18—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted otherwise than in position 3 or 7
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/114—Initiator containing
- Y10S430/12—Nitrogen compound containing
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/114—Initiator containing
- Y10S430/122—Sulfur compound containing
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Materials For Photolithography (AREA)
- Polymerisation Methods In General (AREA)
- Paints Or Removers (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Dental Preparations (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH3080/95 | 1995-10-31 | ||
| CH308095 | 1995-10-31 |
Publications (3)
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| JPH09222725A JPH09222725A (ja) | 1997-08-26 |
| JPH09222725A5 JPH09222725A5 (OSRAM) | 2004-10-21 |
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| JP (1) | JP3975411B2 (OSRAM) |
| KR (1) | KR100441135B1 (OSRAM) |
| CN (1) | CN1088855C (OSRAM) |
| AT (1) | AT407157B (OSRAM) |
| AU (1) | AU709583B2 (OSRAM) |
| BE (1) | BE1010726A5 (OSRAM) |
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| MX (1) | MX9605258A (OSRAM) |
| MY (1) | MY117352A (OSRAM) |
| NL (1) | NL1004387C2 (OSRAM) |
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Families Citing this family (35)
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| JP3665166B2 (ja) * | 1996-07-24 | 2005-06-29 | 東京応化工業株式会社 | 化学増幅型レジスト組成物及びそれに用いる酸発生剤 |
| US6770420B2 (en) * | 1996-09-02 | 2004-08-03 | Ciba Specialty Chemicals Corporation | Alkylsulfonyloximes for high-resolution i-line photoresists of high sensitivity |
| TW550439B (en) * | 1997-07-01 | 2003-09-01 | Ciba Sc Holding Ag | New oxime sulfonates as latent acids and compositions and photoresists comprising said oxime sulfonates |
| ES2198906T3 (es) | 1998-03-13 | 2004-02-01 | Akzo Nobel N.V. | Composicion de recubrimiento no acuosa basada en una resina alquidica de secado por oxidacion y un fotoiniciador. |
| JP3853967B2 (ja) * | 1998-04-13 | 2006-12-06 | 富士写真フイルム株式会社 | 熱硬化性組成物およびこれを用いた平版印刷版用原版ならびにスルホン酸エステル化合物 |
| US6280519B1 (en) * | 1998-05-05 | 2001-08-28 | Exxon Chemical Patents Inc. | Environmentally preferred fluids and fluid blends |
| TW575792B (en) * | 1998-08-19 | 2004-02-11 | Ciba Sc Holding Ag | New unsaturated oxime derivatives and the use thereof as latent acids |
| DE69904073T2 (de) | 1998-10-29 | 2003-07-17 | Ciba Speciality Chemicals Holding Inc., Basel | Oximderivate und ihre verwendung als latente saüre |
| DE60028738T2 (de) | 1999-03-03 | 2007-05-24 | Ciba Speciality Chemicals Holding Inc. | Oximderivate und ihre verwendung als photoinitiatoren |
| NL1014545C2 (nl) * | 1999-03-31 | 2002-02-26 | Ciba Sc Holding Ag | Oxim-derivaten en de toepassing daarvan als latente zuren. |
| SG78412A1 (en) | 1999-03-31 | 2001-02-20 | Ciba Sc Holding Ag | Oxime derivatives and the use thereof as latent acids |
| US6797451B2 (en) * | 1999-07-30 | 2004-09-28 | Hynix Semiconductor Inc. | Reflection-inhibiting resin used in process for forming photoresist pattern |
| WO2001055789A2 (en) * | 2000-01-25 | 2001-08-02 | Infineon Technologies Ag | Chemically amplified short wavelength resist |
| JP2001296666A (ja) * | 2000-04-12 | 2001-10-26 | Orc Mfg Co Ltd | 基板露光方法および露光装置 |
| US6482567B1 (en) * | 2000-08-25 | 2002-11-19 | Shipley Company, L.L.C. | Oxime sulfonate and N-oxyimidosulfonate photoacid generators and photoresists comprising same |
| TWI272451B (en) | 2000-09-25 | 2007-02-01 | Ciba Sc Holding Ag | Chemically amplified photoresist composition, process for preparation of a photoresist, and use of said chemically amplified photoresist composition |
| CN100338056C (zh) | 2001-06-01 | 2007-09-19 | 西巴特殊化学品控股有限公司 | 取代的肟衍生物及其作为潜在酸的用途 |
| JP3633595B2 (ja) * | 2001-08-10 | 2005-03-30 | 富士通株式会社 | レジストパターン膨潤化材料およびそれを用いた微小パターンの形成方法および半導体装置の製造方法 |
| JP4951827B2 (ja) * | 2001-08-17 | 2012-06-13 | Jsr株式会社 | スルホニル構造を有する化合物、それを用いた感放射線性酸発生剤、ポジ型感放射線性樹脂組成物、及びネガ型感放射線性樹脂組成物 |
| JP2005517026A (ja) * | 2002-02-06 | 2005-06-09 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | スルホナート誘導体及び潜酸としてのその使用 |
| AT500298A1 (de) * | 2002-06-14 | 2005-11-15 | Agrolinz Melamin Gmbh | Verfahren zur härtung von aminoplasten |
| CA2511979A1 (en) * | 2003-02-19 | 2004-09-02 | Akira Matsumoto | Halogenated oxime derivatives and the use thereof as latent acids |
| JP2004333865A (ja) * | 2003-05-07 | 2004-11-25 | Osaka Gas Co Ltd | 光酸発生剤及びそれを含む光重合性樹脂組成物 |
| CN1989455B (zh) * | 2004-07-20 | 2011-12-21 | 西巴特殊化学品控股有限公司 | 肟衍生物和它们作为潜伏酸的用途 |
| JP4644464B2 (ja) * | 2004-10-19 | 2011-03-02 | 株式会社トクヤマ | 歯科用修復材料 |
| JP4631059B2 (ja) * | 2006-03-30 | 2011-02-16 | 国立大学法人 千葉大学 | 光酸発生材料、これを用いたフォトリソグラフィー材料、光パターニングまたは光リソグラフィー |
| KR20090023720A (ko) * | 2006-06-20 | 2009-03-05 | 시바 홀딩 인크 | 옥심 설포네이트 및 잠산으로서의 이의 용도 |
| CN101506734B (zh) * | 2006-08-24 | 2012-04-11 | 西巴控股有限公司 | Uv量指示剂 |
| KR101439951B1 (ko) | 2007-02-15 | 2014-09-17 | 주식회사 동진쎄미켐 | 설포닐기를 포함하는 포토레지스트 모노머, 폴리머 및 이를 포함하는 포토레지스트 조성물 |
| JP4637221B2 (ja) | 2007-09-28 | 2011-02-23 | 富士フイルム株式会社 | ポジ型感光性樹脂組成物及びそれを用いた硬化膜形成方法 |
| JP5308657B2 (ja) * | 2007-12-10 | 2013-10-09 | 東京応化工業株式会社 | 非イオン性感光性化合物、酸発生剤、レジスト組成物およびレジストパターン形成方法 |
| JP5676179B2 (ja) * | 2010-08-20 | 2015-02-25 | 富士フイルム株式会社 | ポジ型感光性樹脂組成物、硬化膜の形成方法、硬化膜、有機el表示装置、及び、液晶表示装置 |
| JP5335045B2 (ja) * | 2011-08-31 | 2013-11-06 | 富士フイルム株式会社 | 感光性樹脂組成物、オキシムスルホネート化合物、硬化膜の形成方法、硬化膜、有機el表示装置、及び、液晶表示装置 |
| WO2016124493A1 (en) | 2015-02-02 | 2016-08-11 | Basf Se | Latent acids and their use |
| JP6605820B2 (ja) * | 2015-03-11 | 2019-11-13 | 株式会社Adeka | オキシムスルホネート化合物、光酸発生剤、レジスト組成物、カチオン重合開始剤、およびカチオン重合性組成物 |
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|---|---|---|---|---|
| IT1110460B (it) * | 1977-03-02 | 1985-12-23 | Ciba Geigy Ag | Prodotti che favoriscono la crescita delle piante e prodotti che proteggono le piante a base di eteri di ossime e di esteri di ossime loro preparazione e loro impiego |
| US4347372A (en) * | 1978-09-01 | 1982-08-31 | Ciba-Geigy Corporation | Benzoxazolyl-glyoxylonitrile-2-oxime ether derivatives |
| US4346094A (en) * | 1980-09-22 | 1982-08-24 | Eli Lilly And Company | 3-Aryl-5-isothiazolecarboxylic acids and related compounds used to lower uric acid levels |
| US4540598A (en) * | 1983-08-17 | 1985-09-10 | Ciba-Geigy Corporation | Process for curing acid-curable finishes |
| EP0199672B1 (de) * | 1985-04-12 | 1988-06-01 | Ciba-Geigy Ag | Oximsulfonate mit reaktiven Gruppen |
| GB8608528D0 (en) * | 1986-04-08 | 1986-05-14 | Ciba Geigy Ag | Production of positive images |
| EP0361907A3 (en) * | 1988-09-29 | 1991-05-02 | Hoechst Celanese Corporation | Photoresist compositions for deep uv image reversal |
| DE59309494D1 (de) * | 1992-05-22 | 1999-05-12 | Ciba Geigy Ag | Hochauflösender I-Linien Photoresist mit höherer Empfindlichkeit |
| GB9220986D0 (en) * | 1992-10-06 | 1992-11-18 | Ciba Geigy Ag | Chemical composition |
| JP3830183B2 (ja) * | 1995-09-29 | 2006-10-04 | 東京応化工業株式会社 | オキシムスルホネート化合物及びレジスト用酸発生剤 |
-
1996
- 1996-10-17 MY MYPI96004312A patent/MY117352A/en unknown
- 1996-10-18 GB GB9621798A patent/GB2306958B/en not_active Expired - Fee Related
- 1996-10-23 CH CH02598/96A patent/CH691630A5/de not_active IP Right Cessation
- 1996-10-24 AU AU70382/96A patent/AU709583B2/en not_active Ceased
- 1996-10-28 DE DE19644797A patent/DE19644797A1/de not_active Withdrawn
- 1996-10-28 US US08/738,560 patent/US6017675A/en not_active Expired - Lifetime
- 1996-10-29 FR FR9613165A patent/FR2740455B1/fr not_active Expired - Fee Related
- 1996-10-29 SG SG1996011001A patent/SG49984A1/en unknown
- 1996-10-29 CA CA002189110A patent/CA2189110A1/en not_active Abandoned
- 1996-10-30 CN CN96122763A patent/CN1088855C/zh not_active Expired - Lifetime
- 1996-10-30 NL NL1004387A patent/NL1004387C2/nl not_active IP Right Cessation
- 1996-10-30 KR KR1019960051718A patent/KR100441135B1/ko not_active Expired - Lifetime
- 1996-10-30 AT AT0190596A patent/AT407157B/de not_active IP Right Cessation
- 1996-10-30 IT IT96MI002251A patent/IT1286067B1/it active IP Right Grant
- 1996-10-30 ES ES09602295A patent/ES2122916B1/es not_active Expired - Fee Related
- 1996-10-31 MX MX9605258A patent/MX9605258A/es not_active IP Right Cessation
- 1996-10-31 BE BE9600924A patent/BE1010726A5/fr not_active IP Right Cessation
- 1996-10-31 JP JP30583496A patent/JP3975411B2/ja not_active Expired - Lifetime
- 1996-10-31 BR BR9605394A patent/BR9605394A/pt active Search and Examination
Also Published As
| Publication number | Publication date |
|---|---|
| ATA190596A (de) | 2000-05-15 |
| BR9605394A (pt) | 1998-07-28 |
| ES2122916A1 (es) | 1998-12-16 |
| KR100441135B1 (ko) | 2004-10-02 |
| FR2740455B1 (fr) | 1999-01-29 |
| DE19644797A1 (de) | 1997-05-07 |
| CA2189110A1 (en) | 1997-05-01 |
| NL1004387A1 (nl) | 1997-05-02 |
| AT407157B (de) | 2001-01-25 |
| FR2740455A1 (fr) | 1997-04-30 |
| GB2306958A (en) | 1997-05-14 |
| MY117352A (en) | 2004-06-30 |
| CH691630A5 (de) | 2001-08-31 |
| GB2306958B (en) | 1999-12-15 |
| GB9621798D0 (en) | 1996-12-11 |
| MX9605258A (es) | 1997-04-30 |
| AU709583B2 (en) | 1999-09-02 |
| SG49984A1 (en) | 2001-01-16 |
| ES2122916B1 (es) | 1999-08-16 |
| NL1004387C2 (nl) | 1998-05-19 |
| CN1088855C (zh) | 2002-08-07 |
| JPH09222725A (ja) | 1997-08-26 |
| KR970022553A (ko) | 1997-05-30 |
| AU7038296A (en) | 1997-05-08 |
| US6017675A (en) | 2000-01-25 |
| CN1153926A (zh) | 1997-07-09 |
| ITMI962251A1 (it) | 1998-04-30 |
| IT1286067B1 (it) | 1998-07-07 |
| BE1010726A5 (fr) | 1998-12-01 |
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