KR100634942B1 - 감방사선성 수지 조성물 - Google Patents
감방사선성 수지 조성물 Download PDFInfo
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- KR100634942B1 KR100634942B1 KR1020000059689A KR20000059689A KR100634942B1 KR 100634942 B1 KR100634942 B1 KR 100634942B1 KR 1020000059689 A KR1020000059689 A KR 1020000059689A KR 20000059689 A KR20000059689 A KR 20000059689A KR 100634942 B1 KR100634942 B1 KR 100634942B1
- Authority
- KR
- South Korea
- Prior art keywords
- group
- copolymer
- methylstyrene
- formula
- resin composition
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 38
- -1 salt compound Chemical class 0.000 claims abstract description 217
- 229920001577 copolymer Polymers 0.000 claims abstract description 108
- 230000005855 radiation Effects 0.000 claims abstract description 52
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 claims abstract description 38
- 125000003118 aryl group Chemical group 0.000 claims abstract description 25
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 9
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 7
- 150000001768 cations Chemical class 0.000 claims abstract description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000011593 sulfur Substances 0.000 claims abstract description 4
- 239000011347 resin Substances 0.000 claims description 85
- 229920005989 resin Polymers 0.000 claims description 85
- 239000002253 acid Substances 0.000 claims description 76
- 239000000178 monomer Substances 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 26
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- GRFNSWBVXHLTCI-UHFFFAOYSA-N 1-ethenyl-4-[(2-methylpropan-2-yl)oxy]benzene Chemical compound CC(C)(C)OC1=CC=C(C=C)C=C1 GRFNSWBVXHLTCI-UHFFFAOYSA-N 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- 125000000962 organic group Chemical group 0.000 claims description 13
- 239000003513 alkali Substances 0.000 claims description 12
- 238000009792 diffusion process Methods 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 239000004094 surface-active agent Substances 0.000 claims description 9
- 125000004434 sulfur atom Chemical group 0.000 claims description 7
- JAMNSIXSLVPNLC-UHFFFAOYSA-N (4-ethenylphenyl) acetate Chemical compound CC(=O)OC1=CC=C(C=C)C=C1 JAMNSIXSLVPNLC-UHFFFAOYSA-N 0.000 claims description 5
- UREMSSBPHKOOSD-UHFFFAOYSA-N 1-(1-cyclohexyloxyethoxy)-4-ethenylbenzene Chemical compound C=1C=C(C=C)C=CC=1OC(C)OC1CCCCC1 UREMSSBPHKOOSD-UHFFFAOYSA-N 0.000 claims description 5
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 5
- LQDGDDQWVWZDCS-UHFFFAOYSA-N 1-[(2-methylpropan-2-yl)oxy]-4-prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=C(OC(C)(C)C)C=C1 LQDGDDQWVWZDCS-UHFFFAOYSA-N 0.000 claims description 4
- DTNCNFLLRLHPNJ-UHFFFAOYSA-N 1-ethenyl-4-(1-ethoxyethoxy)benzene Chemical compound CCOC(C)OC1=CC=C(C=C)C=C1 DTNCNFLLRLHPNJ-UHFFFAOYSA-N 0.000 claims description 4
- MGJHVJKUHCWETL-UHFFFAOYSA-N 1-ethenyl-4-(1-methoxyethoxy)benzene Chemical compound COC(C)OC1=CC=C(C=C)C=C1 MGJHVJKUHCWETL-UHFFFAOYSA-N 0.000 claims description 4
- JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical compound OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000000524 functional group Chemical group 0.000 claims description 4
- LTGJSMARDKHZOY-UHFFFAOYSA-N 1-ethenyl-3-[(2-methylpropan-2-yl)oxy]benzene Chemical compound CC(C)(C)OC1=CC=CC(C=C)=C1 LTGJSMARDKHZOY-UHFFFAOYSA-N 0.000 claims description 3
- UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-UHFFFAOYSA-N 0.000 claims description 3
- YNGIFMKMDRDNBQ-UHFFFAOYSA-N 3-ethenylphenol Chemical compound OC1=CC=CC(C=C)=C1 YNGIFMKMDRDNBQ-UHFFFAOYSA-N 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 3
- 239000002736 nonionic surfactant Substances 0.000 claims description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 3
- ONOWUOBSPYRKIT-UHFFFAOYSA-N 1-(1-ethoxyethoxy)-2-methyl-4-prop-1-en-2-ylbenzene Chemical compound CCOC(C)OC1=CC=C(C(C)=C)C=C1C ONOWUOBSPYRKIT-UHFFFAOYSA-N 0.000 claims description 2
- JZYNJJOGGPQAMQ-UHFFFAOYSA-N 1-(1-ethoxyethoxy)-2-prop-1-en-2-ylbenzene Chemical compound CCOC(C)OC1=CC=CC=C1C(C)=C JZYNJJOGGPQAMQ-UHFFFAOYSA-N 0.000 claims description 2
- XYBPTYWZXMZXIB-UHFFFAOYSA-N 1-(1-ethoxyethoxy)-3-prop-1-en-2-ylbenzene Chemical compound CCOC(C)OC1=CC=CC(C(C)=C)=C1 XYBPTYWZXMZXIB-UHFFFAOYSA-N 0.000 claims description 2
- VHJMAPSVGREZMK-UHFFFAOYSA-N 1-(1-ethoxyethoxy)-4-prop-1-en-2-ylbenzene Chemical compound CCOC(C)OC1=CC=C(C(C)=C)C=C1 VHJMAPSVGREZMK-UHFFFAOYSA-N 0.000 claims description 2
- KTTHPHUZVYCKOG-UHFFFAOYSA-N 1-(1-methoxyethoxy)-2-methyl-4-prop-1-en-2-ylbenzene Chemical compound COC(C)OC1=CC=C(C(C)=C)C=C1C KTTHPHUZVYCKOG-UHFFFAOYSA-N 0.000 claims description 2
- GPOLEWSNBUQUGJ-UHFFFAOYSA-N 1-(1-methoxyethoxy)-2-prop-1-en-2-ylbenzene Chemical compound COC(C)OC1=CC=CC=C1C(C)=C GPOLEWSNBUQUGJ-UHFFFAOYSA-N 0.000 claims description 2
- IZYHCUTTWJQLSK-UHFFFAOYSA-N 1-(2-methylbutan-2-yloxy)-4-prop-1-en-2-ylbenzene Chemical compound CCC(C)(C)OC1=CC=C(C(C)=C)C=C1 IZYHCUTTWJQLSK-UHFFFAOYSA-N 0.000 claims description 2
- VXNGVPKOXYLSRK-UHFFFAOYSA-N 1-(cyclohexyloxymethoxy)-4-ethenylbenzene Chemical compound C1=CC(C=C)=CC=C1OCOC1CCCCC1 VXNGVPKOXYLSRK-UHFFFAOYSA-N 0.000 claims description 2
- FBYXNFZLPUOWMR-UHFFFAOYSA-N 1-(cyclohexyloxymethoxy)-4-prop-1-en-2-ylbenzene Chemical compound C1=CC(C(=C)C)=CC=C1OCOC1CCCCC1 FBYXNFZLPUOWMR-UHFFFAOYSA-N 0.000 claims description 2
- XWLIOMSBRVOFLM-UHFFFAOYSA-N 1-(ethoxymethoxy)-2-methyl-4-prop-1-en-2-ylbenzene Chemical compound CCOCOC1=CC=C(C(C)=C)C=C1C XWLIOMSBRVOFLM-UHFFFAOYSA-N 0.000 claims description 2
- QLJWHDWFRGGINY-UHFFFAOYSA-N 1-(ethoxymethoxy)-2-prop-1-en-2-ylbenzene Chemical compound CCOCOC1=CC=CC=C1C(C)=C QLJWHDWFRGGINY-UHFFFAOYSA-N 0.000 claims description 2
- AXSYMWGTTFSZNI-UHFFFAOYSA-N 1-(ethoxymethoxy)-3-prop-1-en-2-ylbenzene Chemical compound CCOCOC1=CC=CC(C(C)=C)=C1 AXSYMWGTTFSZNI-UHFFFAOYSA-N 0.000 claims description 2
- YZNLEHDNNBEODS-UHFFFAOYSA-N 1-(ethoxymethoxy)-4-prop-1-en-2-ylbenzene Chemical compound CCOCOC1=CC=C(C(C)=C)C=C1 YZNLEHDNNBEODS-UHFFFAOYSA-N 0.000 claims description 2
- WXEPTQLFHRYWSB-UHFFFAOYSA-N 1-(methoxymethoxy)-2-methyl-4-prop-1-en-2-ylbenzene Chemical compound COCOC1=CC=C(C(C)=C)C=C1C WXEPTQLFHRYWSB-UHFFFAOYSA-N 0.000 claims description 2
- MVNYXBZNVOPHNS-UHFFFAOYSA-N 1-(methoxymethoxy)-2-prop-1-en-2-ylbenzene Chemical compound COCOC1=CC=CC=C1C(C)=C MVNYXBZNVOPHNS-UHFFFAOYSA-N 0.000 claims description 2
- BGGCRLDTSYEWDR-UHFFFAOYSA-N 1-(methoxymethoxy)-3-prop-1-en-2-ylbenzene Chemical compound COCOC1=CC=CC(C(C)=C)=C1 BGGCRLDTSYEWDR-UHFFFAOYSA-N 0.000 claims description 2
- VEIAFFZSFAYZKE-UHFFFAOYSA-N 1-(methoxymethoxy)-4-prop-1-en-2-ylbenzene Chemical compound COCOC1=CC=C(C(C)=C)C=C1 VEIAFFZSFAYZKE-UHFFFAOYSA-N 0.000 claims description 2
- SRJHPZBDCRYCEV-UHFFFAOYSA-N 1-[(2-methylpropan-2-yl)oxy]-2-prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=CC=C1OC(C)(C)C SRJHPZBDCRYCEV-UHFFFAOYSA-N 0.000 claims description 2
- QRSPZQBJIPLLOR-UHFFFAOYSA-N 1-[(2-methylpropan-2-yl)oxy]-3-prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=CC(OC(C)(C)C)=C1 QRSPZQBJIPLLOR-UHFFFAOYSA-N 0.000 claims description 2
- NVCDZYPRNSWBHV-UHFFFAOYSA-N 1-ethenyl-2-(1-ethoxyethoxy)benzene Chemical compound CCOC(C)OC1=CC=CC=C1C=C NVCDZYPRNSWBHV-UHFFFAOYSA-N 0.000 claims description 2
- WXUKMNJGBXGFPL-UHFFFAOYSA-N 1-ethenyl-2-(1-methoxyethoxy)benzene Chemical compound COC(C)OC1=CC=CC=C1C=C WXUKMNJGBXGFPL-UHFFFAOYSA-N 0.000 claims description 2
- OGBVTXSHQPTJJM-UHFFFAOYSA-N 1-ethenyl-2-(ethoxymethoxy)benzene Chemical compound CCOCOC1=CC=CC=C1C=C OGBVTXSHQPTJJM-UHFFFAOYSA-N 0.000 claims description 2
- TVJXQORCQHAAFZ-UHFFFAOYSA-N 1-ethenyl-2-(methoxymethoxy)benzene Chemical compound COCOC1=CC=CC=C1C=C TVJXQORCQHAAFZ-UHFFFAOYSA-N 0.000 claims description 2
- CCSZEZULHZMGHK-UHFFFAOYSA-N 1-ethenyl-2-[(2-methylpropan-2-yl)oxy]benzene Chemical compound CC(C)(C)OC1=CC=CC=C1C=C CCSZEZULHZMGHK-UHFFFAOYSA-N 0.000 claims description 2
- UKPZKFBBVPKVIC-UHFFFAOYSA-N 1-ethenyl-3-(1-ethoxyethoxy)benzene Chemical compound CCOC(C)OC1=CC=CC(C=C)=C1 UKPZKFBBVPKVIC-UHFFFAOYSA-N 0.000 claims description 2
- DPRALGAFYOTKRR-UHFFFAOYSA-N 1-ethenyl-3-(1-methoxyethoxy)benzene Chemical compound COC(C)OC1=CC=CC(C=C)=C1 DPRALGAFYOTKRR-UHFFFAOYSA-N 0.000 claims description 2
- GMFHFPFAJHESKL-UHFFFAOYSA-N 1-ethenyl-3-(ethoxymethoxy)benzene Chemical compound CCOCOC1=CC=CC(C=C)=C1 GMFHFPFAJHESKL-UHFFFAOYSA-N 0.000 claims description 2
- YYRGFWRHEKGYOX-UHFFFAOYSA-N 1-ethenyl-3-(methoxymethoxy)benzene Chemical compound COCOC1=CC=CC(C=C)=C1 YYRGFWRHEKGYOX-UHFFFAOYSA-N 0.000 claims description 2
- KTCTUVAYZCVCDP-UHFFFAOYSA-N 1-ethenyl-4-(2-methylbutan-2-yloxy)benzene Chemical compound CCC(C)(C)OC1=CC=C(C=C)C=C1 KTCTUVAYZCVCDP-UHFFFAOYSA-N 0.000 claims description 2
- ORYHTUOLVHPSJT-UHFFFAOYSA-N 1-ethenyl-4-(ethoxymethoxy)benzene Chemical compound CCOCOC1=CC=C(C=C)C=C1 ORYHTUOLVHPSJT-UHFFFAOYSA-N 0.000 claims description 2
- CQUFSHRIMFCUBU-UHFFFAOYSA-N 1-ethenyl-4-(methoxymethoxy)benzene Chemical compound COCOC1=CC=C(C=C)C=C1 CQUFSHRIMFCUBU-UHFFFAOYSA-N 0.000 claims description 2
- UITUMGKYHZMNKN-UHFFFAOYSA-N 2-methyl-4-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=C(O)C(C)=C1 UITUMGKYHZMNKN-UHFFFAOYSA-N 0.000 claims description 2
- WUQYBSRMWWRFQH-UHFFFAOYSA-N 2-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=CC=C1O WUQYBSRMWWRFQH-UHFFFAOYSA-N 0.000 claims description 2
- REWLXMVGEZMKSG-UHFFFAOYSA-N 3-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=CC(O)=C1 REWLXMVGEZMKSG-UHFFFAOYSA-N 0.000 claims description 2
- ZNMLGTIMEBAXJF-UHFFFAOYSA-N 4-ethenyl-1-(1-ethoxyethoxy)-2-methylbenzene Chemical compound CCOC(C)OC1=CC=C(C=C)C=C1C ZNMLGTIMEBAXJF-UHFFFAOYSA-N 0.000 claims description 2
- LNHSMUFZYAFNPL-UHFFFAOYSA-N 4-ethenyl-1-(1-methoxyethoxy)-2-methylbenzene Chemical compound COC(C)OC1=CC=C(C=C)C=C1C LNHSMUFZYAFNPL-UHFFFAOYSA-N 0.000 claims description 2
- DZZPPOFMQPIRJB-UHFFFAOYSA-N 4-ethenyl-1-(ethoxymethoxy)-2-methylbenzene Chemical compound CCOCOC1=CC=C(C=C)C=C1C DZZPPOFMQPIRJB-UHFFFAOYSA-N 0.000 claims description 2
- OUCUSMIWOOMKAV-UHFFFAOYSA-N 4-ethenyl-1-(methoxymethoxy)-2-methylbenzene Chemical compound COCOC1=CC=C(C=C)C=C1C OUCUSMIWOOMKAV-UHFFFAOYSA-N 0.000 claims description 2
- BVVKDJRZSVRXPE-UHFFFAOYSA-N 4-ethenyl-2-methyl-1-[(2-methylpropan-2-yl)oxy]benzene Chemical compound CC1=CC(C=C)=CC=C1OC(C)(C)C BVVKDJRZSVRXPE-UHFFFAOYSA-N 0.000 claims description 2
- QKJHNPXSYSFZMJ-UHFFFAOYSA-N 4-ethenyl-2-methylphenol Chemical compound CC1=CC(C=C)=CC=C1O QKJHNPXSYSFZMJ-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- HPQGURCEDWZMJN-UHFFFAOYSA-N 1-(1-methoxyethoxy)-3-prop-1-en-2-ylbenzene Chemical compound COC(C)OC1=CC=CC(C(C)=C)=C1 HPQGURCEDWZMJN-UHFFFAOYSA-N 0.000 claims 1
- 230000035945 sensitivity Effects 0.000 abstract description 12
- IXSGUIFSMPTAGW-UHFFFAOYSA-N 2-(trifluoromethyl)benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1C(F)(F)F IXSGUIFSMPTAGW-UHFFFAOYSA-N 0.000 abstract description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 abstract description 2
- 239000011630 iodine Substances 0.000 abstract description 2
- FRUWCRYDUOZXFA-UHFFFAOYSA-N 2,4-difluorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(F)C=C1F FRUWCRYDUOZXFA-UHFFFAOYSA-N 0.000 abstract 1
- RLTPXEAFDJVHSN-UHFFFAOYSA-N 4-(trifluoromethyl)benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(C(F)(F)F)C=C1 RLTPXEAFDJVHSN-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 21
- 239000000243 solution Substances 0.000 description 20
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000002904 solvent Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 9
- 150000001875 compounds Chemical group 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
- XLLXMBCBJGATSP-UHFFFAOYSA-N 2-phenylethenol Chemical class OC=CC1=CC=CC=C1 XLLXMBCBJGATSP-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 125000004036 acetal group Chemical group 0.000 description 8
- 238000013461 design Methods 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 150000001241 acetals Chemical class 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 230000005587 bubbling Effects 0.000 description 7
- 238000013329 compounding Methods 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 6
- 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 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 6
- 230000008859 change Effects 0.000 description 6
- 238000004132 cross linking Methods 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 238000007334 copolymerization reaction Methods 0.000 description 5
- 238000005227 gel permeation chromatography Methods 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical group 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 150000003839 salts Chemical group 0.000 description 5
- WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 4
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical class C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000003973 alkyl amines Chemical class 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 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
- 238000011161 development Methods 0.000 description 4
- 238000010894 electron beam technology Methods 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 4
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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Images
Classifications
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- 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
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- G—PHYSICS
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- 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
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- G—PHYSICS
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- 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
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
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- 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
- Y10S430/115—Cationic or anionic
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- 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
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- 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
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Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Materials For Photolithography (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
Claims (18)
- (A) 하기 화학식 1로 표시되는 방향족 술폰산 오늄염 화합물 및 (B) 하기 화학식 5로 표시되는 반복 단위와 하기 화학식 6으로 표시되는 반복 단위를 갖는 공중합체 (I) 및(또는) 하기 화학식 5로 표시되는 반복 단위와 하기 화학식 7로 표시되는 반복 단위를 갖는 공중합체 (II)를 함유하는 것을 특징으로 하는 감방사선성 수지 조성물.<화학식 1>Z+X-상기 식에서, Z+는 황 또는 요오드의 오늄 양이온을 나타내고, X-는 하기 화학식 2 내지 4 중 어느 하나의 음이온을 나타낸다.<화학식 2><화학식 3><화학식 4><화학식 5>상기 식에서, R1은 수소 원자 또는 메틸기를 나타내고, R2는 할로겐 원자 또는 탄소수 1 내지 6의 유기기를 나타내고, i는 0 내지 3의 정수이다.<화학식 6>상기 식에서, R3은 수소 원자 또는 메틸기를 나타내고, R4는 탄소수 4 내지 10의 3급 알킬기를 나타내고, R5는 할로겐 원자 또는 탄소수 1 내지 6의 유기기를 나타내고, j는 0 내지 3의 정수이다.<화학식 7>상기 식에서, R6은 수소 원자 또는 메틸기를 나타내고, R7은 수소 원자 또는 탄소수 1 내지 6의 직쇄상, 분지상 또는 환상의 알킬기를 나타내고, R8은 탄소수 1 내지 6의 직쇄상, 분지상 또는 환상의 알킬기를 나타내고, R9는 할로겐 원자 또는 탄소수 1 내지 6의 유기기를 나타내고, k는 0 내지 3의 정수이다.
- 제1항에 있어서, (A) 화학식 1의 Z+가 하기 화학식 8 또는 9로 표시되는 오늄 양이온인 것을 특징으로 하는 감방사선성 수지 조성물.<화학식 8>상기 식에서, R10 내지 R12는 서로 독립적으로 탄소수 1 내지 16 (치환기의 탄소수를 포함함, 이하 동일)의 치환 또는 비치환의 알킬기 또는 탄소수 6 내지 22의 치환 또는 비치환의 아릴기를 나타내고, 또한 R10 내지 R12의 적어도 1개가 상기 아릴기이거나 또는 R10 내지 R12의 적어도 2개가 서로 결합하여 식 중의 황 원자와 함께 환을 형성하고, 남은 R10 내지 R12가 상기 알킬기 또는 상기 아릴기이고, 또한 식 중에 방향족 환을 갖는다.<화학식 9>상기 식에서, R13 및 R14는 서로 독립적으로 탄소수 6 내지 22의 치환 또는 비치환의 아릴기를 나타내거나 또는 R13과 R14가 서로 결합하여 식 중의 요오드 원자와 함께 환을 형성하고, 또한 식 중에 방향족 환을 갖는다.
- 제1항에 있어서, 공중합체 (I)에 있어서, 반복 단위 (5)를 제공하는 단량체가 4-히드록시스티렌, 3-히드록시스티렌, 2-히드록시스티렌, 4-히드록시-α-메틸스티렌, 3-히드록시-α-메틸스티렌, 2-히드록시-α-메틸스티렌, 3-메틸-4-히드록시스티렌, 3-메틸-4-히드록시-α-메틸스티렌으로부터 선택되는 1종 이상인 것을 특징으로 하는 감방사선성 수지 조성물.
- 제1항에 있어서, 공중합체 (I)에 있어서, 반복 단위 (6)를 제공하는 단량체가 4-t-부톡시스티렌, 3-t-부톡시스티렌, 2-t-부톡시스티렌, 4-t-부톡시-α-메틸스티렌, 3-t-부톡시-α-메틸스티렌, 2-t-부톡시-α-메틸스티렌, 3-메틸-4-t-부톡시스티렌, 3-메틸-4-t-부톡시-α-메틸스티렌, 4-(1',1'-디메틸프로폭시)스티렌, 4-(1',1'-디메틸프로폭시)-α-메틸스티렌으로부터 선택되는 1종 이상인 것을 특징으로 하는 감방사선성 수지 조성물.
- 제1항에 있어서, 공중합체 (I)에 있어서, 반복 단위 (5)의 함유율이 전체 반복 단위에 대하여 20 내지 90 몰%인 것을 특징으로 하는 감방사선성 수지 조성물.
- 제1항에 있어서, 공중합체 (I)에 있어서, 반복 단위 (6)의 함유율이 전체 반복 단위에 대하여 10 내지 50 몰%인 것을 특징으로 하는 감방사선성 수지 조성물.
- 제1항에 있어서, 공중합체 (II)에 있어서, 반복 단위 (7)를 제공하는 단량체가 4-메톡시메톡시스티렌, 3-메톡시메톡시스티렌, 2-메톡시메톡시스티렌, 3-메틸-4-메톡시메톡시스티렌, 4-메톡시메톡시-α-메틸스티렌, 3-메톡시메톡시-α-메틸스티렌, 2-메톡시메톡시-α-메틸스티렌, 3-메틸-4-메톡시메톡시-α-메틸스티렌, 4-에톡시메톡시스티렌, 3-에톡시메톡시스티렌, 2-에톡시메톡시스티렌, 3-메틸-4-에톡시메톡시스티렌, 4-에톡시메톡시-α-메틸스티렌, 3-에톡시메톡시-α-메틸스티렌, 2-에톡시메톡시-α-메틸스티렌, 3-메틸-4-에톡시메톡시-α-메틸스티렌, 4-시클로헥실옥시메톡시스티렌, 4-시클로헥실옥시메톡시-α-메틸스티렌, 4-(1'-메톡시에톡시)스티렌, 3-(1'-메톡시에톡시)스티렌, 2-(1'-메톡시에톡시)스티렌, 3-메틸-4-(1'-메톡시에톡시)스티렌, 4-(1'-메톡시에톡시)-α-메틸스티렌, 3-(1'-메톡시에톡시)-α-메틸스티렌, 2-(1'-메톡시에톡시)-α-메틸스티렌, 3-메틸-4-(1'-메톡시에톡시)-α-메틸스티렌, 4-(1'-에톡시에톡시)스티렌, 3-(1'-에톡시에톡시)스티렌, 2-(1'-에톡시에톡시)스티렌, 3-메틸-4-(1'-에톡시에톡시)스티렌, 4-(1'-에톡시에톡시)-α-메틸스티렌, 3-(1'-에톡시에톡시)-α-메틸스티렌, 2-(1'-에톡시에톡시)-α-메틸스티렌, 3-메틸-4-(1'-에톡시에톡시)-α-메틸스티렌, 4-(1'-시클로헥실옥시에톡시)스티렌, 4-(1'-시클로헥실옥시에톡시)-α-메틸스티렌으로부터 선택되는 1종 이상인 것을 특징으로 하는 감방사선성 수지 조성물.
- 제1항에 있어서, 공중합체 (II)에 있어서, 반복 단위 (7)를 제공하는 단량체가 4-(1'-메톡시에톡시)스티렌, 4-(1'-에톡시에톡시)스티렌, 4-(1'-시클로헥실옥시에톡시)스티렌으로부터 선택되는 1종 이상인 것을 특징으로 하는 감방사선성 수지 조성물.
- 제1항에 있어서, 공중합체 (II)에 있어서, 반복 단위 (5)의 함유율이 전체 반복 단위에 대하여 10 내지 95 몰%인 것을 특징으로 하는 감방사선성 수지 조성물.
- 제1항에 있어서, 공중합체 (II)에 있어서, 반복 단위 (7)의 함유율이 전체 반복 단위에 대하여 5 내지 70 몰%인 것을 특징으로 하는 감방사선성 수지 조성물.
- 제1항에 있어서, 공중합체 (II)에 있어서, 반복 단위 (6)를 더 함유하는 것을 특징으로 하는 감방사선성 수지 조성물.
- 제11항에 있어서, 공중합체 (II)에 있어서, 반복 단위 (6)과 반복 단위 (7)의 합계 함유율이 전체 반복 단위에 대하여 10 내지 70 몰%인 것을 특징으로 하는 감방사선성 수지 조성물.
- 제1항에 있어서, 공중합체 (I) 또는 공중합체 (II)가 다른 반복 단위를 함유하고, 다른 반복 단위를 제공하는 단량체가 스티렌, 4-메톡시스티렌, 4-아세톡시스티렌, 이소보로닐아크릴레이트, 트리시클로데카닐아크릴레이트로부터 선택되는 1종 이상인 것을 특징으로 하는 감방사선성 수지 조성물.
- 제1항에 있어서, 공중합체 (I) 또는 공중합체 (II)가 중합성 불포화 결합을 2개 이상 갖는 다관능성 단량체를 사용하여 분지 구조를 도입한 수지인 것을 특징으로 하는 감방사선성 수지 조성물.
- 제1항에 있어서, 공중합체 (I) 및(또는) 공중합체 (II)의 Mw가 1,000 내지 100,000인 것을 특징으로 하는 감방사선성 수지 조성물.
- 제1항에 있어서, 하기 화학식 53 내지 56으로 표시되는 반복 단위를 1종 이상 갖는 알칼리 가용성 수지 중의 산성 관능기의 수소 원자를, 산의 존재 하에 해리할 수 있는 1종 이상의 산 해리성기로 치환한 구조를 갖고, 그 자체로서는 알칼리 불용성 또는 알칼리 난용성의 수지인 다른 산 해리성기 함유 수지를 함유하는 것을 특징으로 하는 감방사선성 수지 조성물.<화학식 53>상기 식에서, R15는 수소 원자 또는 메틸기를 나타내고, 각 R16은 서로 독립적으로 할로겐 원자 또는 탄소수 1 내지 6의 1가의 유기기를 나타내고, m은 0 내지 3의 정수이다.<화학식 54>상기 식에서, R17은 수소 원자 또는 메틸기를 나타낸다.<화학식 55><화학식 56>상기 식에서, R18 내지 R22는 서로 독립적으로 수소 원자 또는 탄소수 1 내지 4의 직쇄상 또는 분지상의 알킬기를 나타낸다.
- 제1항에 있어서, 산 확산 제어제로서 질소 함유 화합물을 더 함유하는 것을 특징으로 하는 감방사선성 수지 조성물.
- 제1항에 있어서, 계면활성제로서 비이온계 계면활성제를 더 함유하는 것을 특징으로 하는 감방사선성 수지 조성물.
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JP2003043679A (ja) * | 2001-07-31 | 2003-02-13 | Jsr Corp | 感放射線性樹脂組成物 |
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DE112004000021T5 (de) * | 2003-05-20 | 2005-07-28 | Tokyo Ohka Kogyo Co., Ltd., Kawasaki | Positiv-Photoresist-Zusammensetzung vom chemisch verstärkten Typ und Methode zur Bildung eines Resistmusters |
JP2004354609A (ja) * | 2003-05-28 | 2004-12-16 | Tokyo Ohka Kogyo Co Ltd | 化学増幅型ポジ型ホトレジスト組成物およびレジストパターンの形成方法 |
CN100549051C (zh) * | 2003-06-26 | 2009-10-14 | 捷时雅株式会社 | 光刻胶聚合物组合物 |
JP2007522262A (ja) * | 2003-06-26 | 2007-08-09 | シミックス・テクノロジーズ・インコーポレイテッド | フォトレジストポリマー |
US7250475B2 (en) * | 2003-06-26 | 2007-07-31 | Symyx Technologies, Inc. | Synthesis of photoresist polymers |
US8062825B2 (en) * | 2004-12-03 | 2011-11-22 | Tokyo Ohka Kogyo Co., Ltd. | Positive resist composition and resist pattern forming method |
JP4715671B2 (ja) * | 2005-08-03 | 2011-07-06 | Jsr株式会社 | メッキ造形物製造用ポジ型感放射線性樹脂組成物、転写フィルムおよびメッキ造形物の製造方法 |
US8715918B2 (en) * | 2007-09-25 | 2014-05-06 | Az Electronic Materials Usa Corp. | Thick film resists |
JP5552365B2 (ja) * | 2009-06-30 | 2014-07-16 | 東京応化工業株式会社 | 接着剤組成物および接着フィルム |
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JP4007570B2 (ja) * | 1998-10-16 | 2007-11-14 | 富士フイルム株式会社 | ポジ型レジスト組成物 |
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