JP2016206586A - レジスト組成物及びパターン形成方法 - Google Patents
レジスト組成物及びパターン形成方法 Download PDFInfo
- Publication number
- JP2016206586A JP2016206586A JP2015091338A JP2015091338A JP2016206586A JP 2016206586 A JP2016206586 A JP 2016206586A JP 2015091338 A JP2015091338 A JP 2015091338A JP 2015091338 A JP2015091338 A JP 2015091338A JP 2016206586 A JP2016206586 A JP 2016206586A
- Authority
- JP
- Japan
- Prior art keywords
- group
- butyl
- methyl
- atom
- ethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 60
- 238000000034 method Methods 0.000 title claims abstract description 37
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 111
- 239000002253 acid Substances 0.000 claims abstract description 71
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 55
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 51
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 50
- 239000003960 organic solvent Substances 0.000 claims abstract description 38
- 239000011347 resin Substances 0.000 claims abstract description 35
- 229920005989 resin Polymers 0.000 claims abstract description 35
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 28
- 150000001875 compounds Chemical class 0.000 claims abstract description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 26
- 230000009471 action Effects 0.000 claims abstract description 9
- -1 sulfonium cation Chemical class 0.000 claims description 180
- 150000002430 hydrocarbons Chemical group 0.000 claims description 69
- 238000011161 development Methods 0.000 claims description 31
- 229910052731 fluorine Inorganic materials 0.000 claims description 31
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 24
- 229910052717 sulfur Inorganic materials 0.000 claims description 23
- 125000004434 sulfur atom Chemical group 0.000 claims description 23
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 22
- 125000001153 fluoro group Chemical group F* 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 150000001450 anions Chemical class 0.000 claims description 16
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 claims description 15
- 150000002596 lactones Chemical group 0.000 claims description 15
- 125000002947 alkylene group Chemical group 0.000 claims description 14
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 claims description 14
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 claims description 13
- 230000001681 protective effect Effects 0.000 claims description 13
- FRDAATYAJDYRNW-UHFFFAOYSA-N 3-methyl-3-pentanol Chemical compound CCC(C)(O)CC FRDAATYAJDYRNW-UHFFFAOYSA-N 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 239000011737 fluorine Substances 0.000 claims description 12
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims description 12
- 239000000758 substrate Substances 0.000 claims description 12
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 11
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims description 10
- PFNHSEQQEPMLNI-UHFFFAOYSA-N 2-methyl-1-pentanol Chemical compound CCCC(C)CO PFNHSEQQEPMLNI-UHFFFAOYSA-N 0.000 claims description 10
- WFRBDWRZVBPBDO-UHFFFAOYSA-N 2-methyl-2-pentanol Chemical compound CCCC(C)(C)O WFRBDWRZVBPBDO-UHFFFAOYSA-N 0.000 claims description 10
- ISTJMQSHILQAEC-UHFFFAOYSA-N 2-methyl-3-pentanol Chemical compound CCC(O)C(C)C ISTJMQSHILQAEC-UHFFFAOYSA-N 0.000 claims description 10
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 10
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
- QNVRIHYSUZMSGM-UHFFFAOYSA-N hexan-2-ol Chemical compound CCCCC(C)O QNVRIHYSUZMSGM-UHFFFAOYSA-N 0.000 claims description 10
- ZOCHHNOQQHDWHG-UHFFFAOYSA-N hexan-3-ol Chemical compound CCCC(O)CC ZOCHHNOQQHDWHG-UHFFFAOYSA-N 0.000 claims description 10
- 230000002209 hydrophobic effect Effects 0.000 claims description 10
- 238000007654 immersion Methods 0.000 claims description 10
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 claims description 10
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 10
- KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 claims description 10
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 claims description 10
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 9
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 claims description 9
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 claims description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 9
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 9
- 150000008053 sultones Chemical class 0.000 claims description 9
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical group CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 claims description 8
- UJBOOUHRTQVGRU-UHFFFAOYSA-N 3-methylcyclohexan-1-one Chemical compound CC1CCCC(=O)C1 UJBOOUHRTQVGRU-UHFFFAOYSA-N 0.000 claims description 8
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 claims description 8
- VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 claims description 8
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 8
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 claims description 8
- NMJJFJNHVMGPGM-UHFFFAOYSA-N butyl formate Chemical compound CCCCOC=O NMJJFJNHVMGPGM-UHFFFAOYSA-N 0.000 claims description 8
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 claims description 8
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 claims description 8
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 claims description 8
- 125000005647 linker group Chemical group 0.000 claims description 8
- RPUSRLKKXPQSGP-UHFFFAOYSA-N methyl 3-phenylpropanoate Chemical compound COC(=O)CCC1=CC=CC=C1 RPUSRLKKXPQSGP-UHFFFAOYSA-N 0.000 claims description 8
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 8
- HNBDRPTVWVGKBR-UHFFFAOYSA-N n-pentanoic acid methyl ester Natural products CCCCC(=O)OC HNBDRPTVWVGKBR-UHFFFAOYSA-N 0.000 claims description 8
- 125000004957 naphthylene group Chemical group 0.000 claims description 8
- VKCYHJWLYTUGCC-UHFFFAOYSA-N nonan-2-one Chemical compound CCCCCCCC(C)=O VKCYHJWLYTUGCC-UHFFFAOYSA-N 0.000 claims description 8
- AQIXEPGDORPWBJ-UHFFFAOYSA-N pentan-3-ol Chemical compound CCC(O)CC AQIXEPGDORPWBJ-UHFFFAOYSA-N 0.000 claims description 8
- PGMYKACGEOXYJE-UHFFFAOYSA-N pentyl acetate Chemical compound CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 claims description 8
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 7
- KEBDNKNVCHQIJU-UHFFFAOYSA-N 2-Methylpropyl 3-methylbutanoate Chemical compound CC(C)COC(=O)CC(C)C KEBDNKNVCHQIJU-UHFFFAOYSA-N 0.000 claims description 6
- UBLAMKHIFZBBSS-UHFFFAOYSA-N 3-Methylbutyl pentanoate Chemical compound CCCCC(=O)OCCC(C)C UBLAMKHIFZBBSS-UHFFFAOYSA-N 0.000 claims description 6
- RHLVCLIPMVJYKS-UHFFFAOYSA-N 3-octanone Chemical compound CCCCCC(=O)CC RHLVCLIPMVJYKS-UHFFFAOYSA-N 0.000 claims description 6
- GNKZMNRKLCTJAY-UHFFFAOYSA-N 4'-Methylacetophenone Chemical compound CC(=O)C1=CC=C(C)C=C1 GNKZMNRKLCTJAY-UHFFFAOYSA-N 0.000 claims description 6
- IYTXKIXETAELAV-UHFFFAOYSA-N Aethyl-n-hexyl-keton Natural products CCCCCCC(=O)CC IYTXKIXETAELAV-UHFFFAOYSA-N 0.000 claims description 6
- UYWQUFXKFGHYNT-UHFFFAOYSA-N Benzylformate Chemical compound O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 6
- XINCECQTMHSORG-UHFFFAOYSA-N Isoamyl isovalerate Chemical compound CC(C)CCOC(=O)CC(C)C XINCECQTMHSORG-UHFFFAOYSA-N 0.000 claims description 6
- CRZQGDNQQAALAY-UHFFFAOYSA-N Methyl benzeneacetate Chemical compound COC(=O)CC1=CC=CC=C1 CRZQGDNQQAALAY-UHFFFAOYSA-N 0.000 claims description 6
- TYBCSQFBSWACAA-UHFFFAOYSA-N Nonan-4-one Chemical compound CCCCCC(=O)CCC TYBCSQFBSWACAA-UHFFFAOYSA-N 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 claims description 6
- XUPYJHCZDLZNFP-UHFFFAOYSA-N butyl butanoate Chemical compound CCCCOC(=O)CCC XUPYJHCZDLZNFP-UHFFFAOYSA-N 0.000 claims description 6
- HCRBXQFHJMCTLF-ZCFIWIBFSA-N ethyl (2r)-2-methylbutanoate Chemical compound CCOC(=O)[C@H](C)CC HCRBXQFHJMCTLF-ZCFIWIBFSA-N 0.000 claims description 6
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 claims description 6
- PPXUHEORWJQRHJ-UHFFFAOYSA-N ethyl isovalerate Chemical compound CCOC(=O)CC(C)C PPXUHEORWJQRHJ-UHFFFAOYSA-N 0.000 claims description 6
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- AOGQPLXWSUTHQB-UHFFFAOYSA-N hexyl acetate Chemical compound CCCCCCOC(C)=O AOGQPLXWSUTHQB-UHFFFAOYSA-N 0.000 claims description 6
- RGFNRWTWDWVHDD-UHFFFAOYSA-N isobutyl butyrate Chemical compound CCCC(=O)OCC(C)C RGFNRWTWDWVHDD-UHFFFAOYSA-N 0.000 claims description 6
- WSGCRAOTEDLMFQ-UHFFFAOYSA-N nonan-5-one Chemical compound CCCCC(=O)CCCC WSGCRAOTEDLMFQ-UHFFFAOYSA-N 0.000 claims description 6
- MDHYEMXUFSJLGV-UHFFFAOYSA-N phenethyl acetate Chemical compound CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 claims description 6
- OCAIYHCKLADPEG-UHFFFAOYSA-N propan-2-yl pentanoate Chemical compound CCCCC(=O)OC(C)C OCAIYHCKLADPEG-UHFFFAOYSA-N 0.000 claims description 6
- QNVRIHYSUZMSGM-LURJTMIESA-N 2-Hexanol Natural products CCCC[C@H](C)O QNVRIHYSUZMSGM-LURJTMIESA-N 0.000 claims description 5
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 claims description 5
- ZXNBBWHRUSXUFZ-UHFFFAOYSA-N 3-methyl-2-pentanol Chemical compound CCC(C)C(C)O ZXNBBWHRUSXUFZ-UHFFFAOYSA-N 0.000 claims description 5
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 claims description 5
- PCWGTDULNUVNBN-UHFFFAOYSA-N 4-methylpentan-1-ol Chemical compound CC(C)CCCO PCWGTDULNUVNBN-UHFFFAOYSA-N 0.000 claims description 5
- DIRDKDDFAMNBNY-UHFFFAOYSA-N Isopropyl 2-methylbutanoate Chemical compound CCC(C)C(=O)OC(C)C DIRDKDDFAMNBNY-UHFFFAOYSA-N 0.000 claims description 5
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000011248 coating agent Substances 0.000 claims description 5
- 238000000576 coating method Methods 0.000 claims description 5
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 claims description 5
- 229940035429 isobutyl alcohol Drugs 0.000 claims description 5
- DFOXKPDFWGNLJU-UHFFFAOYSA-N pinacolyl alcohol Chemical compound CC(O)C(C)(C)C DFOXKPDFWGNLJU-UHFFFAOYSA-N 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- ULPMRIXXHGUZFA-UHFFFAOYSA-N (R)-4-Methyl-3-hexanone Natural products CCC(C)C(=O)CC ULPMRIXXHGUZFA-UHFFFAOYSA-N 0.000 claims description 4
- JLIDRDJNLAWIKT-UHFFFAOYSA-N 1,2-dimethyl-3h-benzo[e]indole Chemical compound C1=CC=CC2=C(C(=C(C)N3)C)C3=CC=C21 JLIDRDJNLAWIKT-UHFFFAOYSA-N 0.000 claims description 4
- YXWWHNCQZBVZPV-UHFFFAOYSA-N 2'-methylacetophenone Chemical compound CC(=O)C1=CC=CC=C1C YXWWHNCQZBVZPV-UHFFFAOYSA-N 0.000 claims description 4
- ZSDQQJHSRVEGTJ-UHFFFAOYSA-N 2-(6-amino-1h-indol-3-yl)acetonitrile Chemical compound NC1=CC=C2C(CC#N)=CNC2=C1 ZSDQQJHSRVEGTJ-UHFFFAOYSA-N 0.000 claims description 4
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 claims description 4
- AVMSWPWPYJVYKY-UHFFFAOYSA-N 2-Methylpropyl formate Chemical compound CC(C)COC=O AVMSWPWPYJVYKY-UHFFFAOYSA-N 0.000 claims description 4
- QGLVWTFUWVTDEQ-UHFFFAOYSA-N 2-chloro-3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1Cl QGLVWTFUWVTDEQ-UHFFFAOYSA-N 0.000 claims description 4
- LFSAPCRASZRSKS-UHFFFAOYSA-N 2-methylcyclohexan-1-one Chemical compound CC1CCCCC1=O LFSAPCRASZRSKS-UHFFFAOYSA-N 0.000 claims description 4
- WBPAQKQBUKYCJS-UHFFFAOYSA-N 2-methylpropyl 2-hydroxypropanoate Chemical compound CC(C)COC(=O)C(C)O WBPAQKQBUKYCJS-UHFFFAOYSA-N 0.000 claims description 4
- PFCHFHIRKBAQGU-UHFFFAOYSA-N 3-hexanone Chemical compound CCCC(=O)CC PFCHFHIRKBAQGU-UHFFFAOYSA-N 0.000 claims description 4
- CRORGGSWAKIXSA-UHFFFAOYSA-N 3-methylbutyl 2-hydroxypropanoate Chemical compound CC(C)CCOC(=O)C(C)O CRORGGSWAKIXSA-UHFFFAOYSA-N 0.000 claims description 4
- LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 claims description 4
- MRABAEUHTLLEML-UHFFFAOYSA-N Butyl lactate Chemical compound CCCCOC(=O)C(C)O MRABAEUHTLLEML-UHFFFAOYSA-N 0.000 claims description 4
- NLAMRLZPVVKXTK-SNAWJCMRSA-N [(e)-but-1-enyl] acetate Chemical compound CC\C=C\OC(C)=O NLAMRLZPVVKXTK-SNAWJCMRSA-N 0.000 claims description 4
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 claims description 4
- DULCUDSUACXJJC-UHFFFAOYSA-N benzeneacetic acid ethyl ester Natural products CCOC(=O)CC1=CC=CC=C1 DULCUDSUACXJJC-UHFFFAOYSA-N 0.000 claims description 4
- 229940007550 benzyl acetate Drugs 0.000 claims description 4
- 239000001191 butyl (2R)-2-hydroxypropanoate Substances 0.000 claims description 4
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 4
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 claims description 4
- BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 claims description 4
- 229940116333 ethyl lactate Drugs 0.000 claims description 4
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 claims description 4
- XKYICAQFSCFURC-UHFFFAOYSA-N isoamyl formate Chemical compound CC(C)CCOC=O XKYICAQFSCFURC-UHFFFAOYSA-N 0.000 claims description 4
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 claims description 4
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 claims description 4
- MCVVUJPXSBQTRZ-ONEGZZNKSA-N methyl (e)-but-2-enoate Chemical compound COC(=O)\C=C\C MCVVUJPXSBQTRZ-ONEGZZNKSA-N 0.000 claims description 4
- 229940095102 methyl benzoate Drugs 0.000 claims description 4
- MQWCXKGKQLNYQG-UHFFFAOYSA-N methyl cyclohexan-4-ol Natural products CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 claims description 4
- 229940057867 methyl lactate Drugs 0.000 claims description 4
- MBAHGFJTIVZLFB-UHFFFAOYSA-N methyl pent-2-enoate Chemical compound CCC=CC(=O)OC MBAHGFJTIVZLFB-UHFFFAOYSA-N 0.000 claims description 4
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 4
- GXOHBWLPQHTYPF-UHFFFAOYSA-N pentyl 2-hydroxypropanoate Chemical compound CCCCCOC(=O)C(C)O GXOHBWLPQHTYPF-UHFFFAOYSA-N 0.000 claims description 4
- 229940049953 phenylacetate Drugs 0.000 claims description 4
- WLJVXDMOQOGPHL-UHFFFAOYSA-M phenylacetate Chemical compound [O-]C(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-M 0.000 claims description 4
- ILVGAIQLOCKNQA-UHFFFAOYSA-N propyl 2-hydroxypropanoate Chemical compound CCCOC(=O)C(C)O ILVGAIQLOCKNQA-UHFFFAOYSA-N 0.000 claims description 4
- 229940090181 propyl acetate Drugs 0.000 claims description 4
- JAELLLITIZHOGQ-UHFFFAOYSA-N tert-butyl propanoate Chemical compound CCC(=O)OC(C)(C)C JAELLLITIZHOGQ-UHFFFAOYSA-N 0.000 claims description 4
- HTSABYAWKQAHBT-UHFFFAOYSA-N trans 3-methylcyclohexanol Natural products CC1CCCC(O)C1 HTSABYAWKQAHBT-UHFFFAOYSA-N 0.000 claims description 4
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 4
- VLILFBZIVHDKIJ-UHFFFAOYSA-N 1-(2-ethylphenyl)ethanone Chemical compound CCC1=CC=CC=C1C(C)=O VLILFBZIVHDKIJ-UHFFFAOYSA-N 0.000 claims description 3
- CBHXDVOSUKFRBE-UHFFFAOYSA-N 2,2-diethylbutan-1-ol Chemical compound CCC(CC)(CC)CO CBHXDVOSUKFRBE-UHFFFAOYSA-N 0.000 claims description 3
- RCSBILYQLVXLJG-UHFFFAOYSA-N 2-Propenyl hexanoate Chemical compound CCCCCC(=O)OCC=C RCSBILYQLVXLJG-UHFFFAOYSA-N 0.000 claims description 3
- ZKZHWAJZNZJAKV-UHFFFAOYSA-N 2-bromo-3-methylquinoline Chemical compound C1=CC=C2N=C(Br)C(C)=CC2=C1 ZKZHWAJZNZJAKV-UHFFFAOYSA-N 0.000 claims description 3
- WKYYYUWKFPFVEY-UHFFFAOYSA-N 2-ethylcyclohexan-1-one Chemical compound CCC1CCCCC1=O WKYYYUWKFPFVEY-UHFFFAOYSA-N 0.000 claims description 3
- WOYWLLHHWAMFCB-UHFFFAOYSA-N 2-ethylhexyl acetate Chemical compound CCCCC(CC)COC(C)=O WOYWLLHHWAMFCB-UHFFFAOYSA-N 0.000 claims description 3
- XHIUFYZDQBSEMF-UHFFFAOYSA-N 2-methylbutyl acetate Chemical compound CCC(C)COC(C)=O XHIUFYZDQBSEMF-UHFFFAOYSA-N 0.000 claims description 3
- IEVRHAUJJJBXFH-UHFFFAOYSA-N 3-ethylcyclohexan-1-one Chemical compound CCC1CCCC(=O)C1 IEVRHAUJJJBXFH-UHFFFAOYSA-N 0.000 claims description 3
- OKSDJGWHKXFVME-UHFFFAOYSA-N 4-ethylcyclohexan-1-one Chemical compound CCC1CCC(=O)CC1 OKSDJGWHKXFVME-UHFFFAOYSA-N 0.000 claims description 3
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 claims description 3
- YNMZZHPSYMOGCI-UHFFFAOYSA-N Aethyl-octyl-keton Natural products CCCCCCCCC(=O)CC YNMZZHPSYMOGCI-UHFFFAOYSA-N 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- AYWJSCLAAPJZEF-UHFFFAOYSA-N Butyl 3-methylbutanoate Chemical compound CCCCOC(=O)CC(C)C AYWJSCLAAPJZEF-UHFFFAOYSA-N 0.000 claims description 3
- OKJADYKTJJGKDX-UHFFFAOYSA-N Butyl pentanoate Chemical compound CCCCOC(=O)CCCC OKJADYKTJJGKDX-UHFFFAOYSA-N 0.000 claims description 3
- YYLLIJHXUHJATK-UHFFFAOYSA-N Cyclohexyl acetate Chemical compound CC(=O)OC1CCCCC1 YYLLIJHXUHJATK-UHFFFAOYSA-N 0.000 claims description 3
- HZPKNSYIDSNZKW-UHFFFAOYSA-N Ethyl 2-methylpentanoate Chemical compound CCCC(C)C(=O)OCC HZPKNSYIDSNZKW-UHFFFAOYSA-N 0.000 claims description 3
- ZFDIRQKJPRINOQ-HWKANZROSA-N Ethyl crotonate Chemical compound CCOC(=O)\C=C\C ZFDIRQKJPRINOQ-HWKANZROSA-N 0.000 claims description 3
- ICMAFTSLXCXHRK-UHFFFAOYSA-N Ethyl pentanoate Chemical compound CCCCC(=O)OCC ICMAFTSLXCXHRK-UHFFFAOYSA-N 0.000 claims description 3
- LSJMDWFAADPNAX-UHFFFAOYSA-N Isovaleriansaeure-propylester Natural products CCCOC(=O)CC(C)C LSJMDWFAADPNAX-UHFFFAOYSA-N 0.000 claims description 3
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 claims description 3
- XYVQFUJDGOBPQI-UHFFFAOYSA-N Methyl-2-hydoxyisobutyric acid Chemical compound COC(=O)C(C)(C)O XYVQFUJDGOBPQI-UHFFFAOYSA-N 0.000 claims description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 3
- ROJKPKOYARNFNB-UHFFFAOYSA-N Propyl pentanoate Chemical compound CCCCC(=O)OCCC ROJKPKOYARNFNB-UHFFFAOYSA-N 0.000 claims description 3
- 230000001476 alcoholic effect Effects 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 150000004982 aromatic amines Chemical class 0.000 claims description 3
- UDEWPOVQBGFNGE-UHFFFAOYSA-N benzoic acid n-propyl ester Natural products CCCOC(=O)C1=CC=CC=C1 UDEWPOVQBGFNGE-UHFFFAOYSA-N 0.000 claims description 3
- FCDMDSDHBVPGGE-UHFFFAOYSA-N butyl 2,2-dimethylpropanoate Chemical compound CCCCOC(=O)C(C)(C)C FCDMDSDHBVPGGE-UHFFFAOYSA-N 0.000 claims description 3
- FMVUGLMJUHFPSJ-UHFFFAOYSA-N butyl 2-methylpentanoate Chemical compound CCCCOC(=O)C(C)CCC FMVUGLMJUHFPSJ-UHFFFAOYSA-N 0.000 claims description 3
- URYUTJWQTWWCCN-UHFFFAOYSA-N butyl pent-2-enoate Chemical compound CCCCOC(=O)C=CCC URYUTJWQTWWCCN-UHFFFAOYSA-N 0.000 claims description 3
- 239000001813 ethyl (2R)-2-methylbutanoate Substances 0.000 claims description 3
- HHEIMYAXCOIQCJ-UHFFFAOYSA-N ethyl 2,2-dimethylpropanoate Chemical compound CCOC(=O)C(C)(C)C HHEIMYAXCOIQCJ-UHFFFAOYSA-N 0.000 claims description 3
- GFUIDHWFLMPAGY-UHFFFAOYSA-N ethyl 2-hydroxy-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)O GFUIDHWFLMPAGY-UHFFFAOYSA-N 0.000 claims description 3
- 229940090910 ethyl 2-methylbutyrate Drugs 0.000 claims description 3
- AGMKVZDPATUSMS-UHFFFAOYSA-N ethyl pent-2-enoate Chemical compound CCOC(=O)C=CCC AGMKVZDPATUSMS-UHFFFAOYSA-N 0.000 claims description 3
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 3
- 150000003949 imides Chemical class 0.000 claims description 3
- PQLMXFQTAMDXIZ-UHFFFAOYSA-N isoamyl butyrate Chemical compound CCCC(=O)OCCC(C)C PQLMXFQTAMDXIZ-UHFFFAOYSA-N 0.000 claims description 3
- JSLCOZYBKYHZNL-UHFFFAOYSA-N isobutyric acid butyl ester Natural products CCCCOC(=O)C(C)C JSLCOZYBKYHZNL-UHFFFAOYSA-N 0.000 claims description 3
- 229940017219 methyl propionate Drugs 0.000 claims description 3
- OLXYLDUSSBULGU-UHFFFAOYSA-N methyl pyridine-4-carboxylate Chemical compound COC(=O)C1=CC=NC=C1 OLXYLDUSSBULGU-UHFFFAOYSA-N 0.000 claims description 3
- YWXLSHOWXZUMSR-UHFFFAOYSA-N octan-4-one Chemical compound CCCCC(=O)CCC YWXLSHOWXZUMSR-UHFFFAOYSA-N 0.000 claims description 3
- FKCRAVPPBFWEJD-XVFCMESISA-N orotidine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=C1C(O)=O FKCRAVPPBFWEJD-XVFCMESISA-N 0.000 claims description 3
- NODGRWCMFMEGJH-UHFFFAOYSA-N p-ethylacetophenone Chemical compound CCC1=CC=C(C(C)=O)C=C1 NODGRWCMFMEGJH-UHFFFAOYSA-N 0.000 claims description 3
- FGPPDYNPZTUNIU-UHFFFAOYSA-N pentyl pentanoate Chemical compound CCCCCOC(=O)CCCC FGPPDYNPZTUNIU-UHFFFAOYSA-N 0.000 claims description 3
- 150000003139 primary aliphatic amines Chemical class 0.000 claims description 3
- PMFKTHJAJBPRNM-UHFFFAOYSA-N propan-2-yl 2,2-dimethylpropanoate Chemical compound CC(C)OC(=O)C(C)(C)C PMFKTHJAJBPRNM-UHFFFAOYSA-N 0.000 claims description 3
- OKSNIKMUZNYBPP-UHFFFAOYSA-N propan-2-yl pent-2-enoate Chemical compound CCC=CC(=O)OC(C)C OKSNIKMUZNYBPP-UHFFFAOYSA-N 0.000 claims description 3
- QMKUYPGVVVLYSR-UHFFFAOYSA-N propyl 2,2-dimethylpropanoate Chemical compound CCCOC(=O)C(C)(C)C QMKUYPGVVVLYSR-UHFFFAOYSA-N 0.000 claims description 3
- HUAZGNHGCJGYNP-UHFFFAOYSA-N propyl butyrate Chemical compound CCCOC(=O)CCC HUAZGNHGCJGYNP-UHFFFAOYSA-N 0.000 claims description 3
- KGUBSOCXRUPVMO-UHFFFAOYSA-N propyl pent-2-enoate Chemical compound CCCOC(=O)C=CCC KGUBSOCXRUPVMO-UHFFFAOYSA-N 0.000 claims description 3
- 150000005619 secondary aliphatic amines Chemical class 0.000 claims description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
- VXHFNALHLRWIIU-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)OC(=O)C(C)(C)C VXHFNALHLRWIIU-UHFFFAOYSA-N 0.000 claims description 3
- ZKAODOPIAGAVNQ-UHFFFAOYSA-N tert-butyl 3-methylbutanoate Chemical compound CC(C)CC(=O)OC(C)(C)C ZKAODOPIAGAVNQ-UHFFFAOYSA-N 0.000 claims description 3
- TWBUVVYSQBFVGZ-UHFFFAOYSA-N tert-butyl butanoate Chemical compound CCCC(=O)OC(C)(C)C TWBUVVYSQBFVGZ-UHFFFAOYSA-N 0.000 claims description 3
- RMMULFUBQFKFRL-UHFFFAOYSA-N tert-butyl pent-2-enoate Chemical compound CCC=CC(=O)OC(C)(C)C RMMULFUBQFKFRL-UHFFFAOYSA-N 0.000 claims description 3
- SCSLUABEVMLYEA-UHFFFAOYSA-N tert-butyl pentanoate Chemical compound CCCCC(=O)OC(C)(C)C SCSLUABEVMLYEA-UHFFFAOYSA-N 0.000 claims description 3
- 150000003510 tertiary aliphatic amines Chemical class 0.000 claims description 3
- ZFDIRQKJPRINOQ-UHFFFAOYSA-N transbutenic acid ethyl ester Natural products CCOC(=O)C=CC ZFDIRQKJPRINOQ-UHFFFAOYSA-N 0.000 claims description 3
- HFZLSTDPRQSZCQ-UHFFFAOYSA-N 1-pyrrolidin-3-ylpyrrolidine Chemical compound C1CCCN1C1CNCC1 HFZLSTDPRQSZCQ-UHFFFAOYSA-N 0.000 claims description 2
- SMIKUJGCXFBSEI-UHFFFAOYSA-N CC(CCO)(C)C.CC(C)(C(C)C)O Chemical compound CC(CCO)(C)C.CC(C)(C(C)C)O SMIKUJGCXFBSEI-UHFFFAOYSA-N 0.000 claims description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 2
- 150000007514 bases Chemical class 0.000 claims description 2
- XSBSXJAYEPDGSF-UHFFFAOYSA-N diethyl 3,5-dimethyl-1h-pyrrole-2,4-dicarboxylate Chemical compound CCOC(=O)C=1NC(C)=C(C(=O)OCC)C=1C XSBSXJAYEPDGSF-UHFFFAOYSA-N 0.000 claims description 2
- 238000010894 electron beam technology Methods 0.000 claims description 2
- 229940044170 formate Drugs 0.000 claims description 2
- ZHDCHCTZRODSEN-HWKANZROSA-N propyl (e)-but-2-enoate Chemical compound CCCOC(=O)\C=C\C ZHDCHCTZRODSEN-HWKANZROSA-N 0.000 claims description 2
- QHSPZGZEUDEIQM-AATRIKPKSA-N tert-butyl (e)-but-2-enoate Chemical compound C\C=C\C(=O)OC(C)(C)C QHSPZGZEUDEIQM-AATRIKPKSA-N 0.000 claims description 2
- AABBHSMFGKYLKE-SNAWJCMRSA-N propan-2-yl (e)-but-2-enoate Chemical compound C\C=C\C(=O)OC(C)C AABBHSMFGKYLKE-SNAWJCMRSA-N 0.000 claims 1
- 230000007261 regionalization Effects 0.000 abstract description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 0 C*C(C(*)=N)=CI Chemical compound C*C(C(*)=N)=CI 0.000 description 71
- 230000018109 developmental process Effects 0.000 description 30
- 239000002585 base Substances 0.000 description 27
- 125000000217 alkyl group Chemical group 0.000 description 25
- 102100028626 4-hydroxyphenylpyruvate dioxygenase Human genes 0.000 description 23
- 229920002469 poly(p-dioxane) polymer Polymers 0.000 description 23
- 150000001721 carbon Chemical group 0.000 description 19
- 125000004430 oxygen atom Chemical group O* 0.000 description 19
- 239000002904 solvent Substances 0.000 description 18
- 239000004094 surface-active agent Substances 0.000 description 18
- 229920000642 polymer Polymers 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 description 13
- 150000003839 salts Chemical class 0.000 description 13
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 238000009792 diffusion process Methods 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 10
- 230000008859 change Effects 0.000 description 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 125000006165 cyclic alkyl group Chemical group 0.000 description 8
- 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 8
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 8
- 239000000178 monomer Substances 0.000 description 8
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 7
- 125000005843 halogen group Chemical group 0.000 description 7
- 238000001459 lithography Methods 0.000 description 7
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- IWTBVKIGCDZRPL-UHFFFAOYSA-N 3-methylpentanol Chemical compound CCC(C)CCO IWTBVKIGCDZRPL-UHFFFAOYSA-N 0.000 description 6
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 238000013329 compounding Methods 0.000 description 6
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 6
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 125000001624 naphthyl group Chemical group 0.000 description 6
- 125000005188 oxoalkyl group Chemical group 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 125000003282 alkyl amino group Chemical group 0.000 description 5
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 5
- 125000001188 haloalkyl group Chemical group 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 5
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 5
- 125000004043 oxo group Chemical group O=* 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 description 4
- IKDIJXDZEYHZSD-UHFFFAOYSA-N 2-phenylethyl formate Chemical compound O=COCCC1=CC=CC=C1 IKDIJXDZEYHZSD-UHFFFAOYSA-N 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 238000000671 immersion lithography Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000012046 mixed solvent Substances 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- 125000004665 trialkylsilyl group Chemical group 0.000 description 4
- 235000012431 wafers Nutrition 0.000 description 4
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical group FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 3
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 3
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 3
- IKECULIHBUCAKR-UHFFFAOYSA-N 2,3-dimethylbutan-2-ol Chemical compound CC(C)C(C)(C)O IKECULIHBUCAKR-UHFFFAOYSA-N 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 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 102000046669 Surf-1 Human genes 0.000 description 3
- 108060007963 Surf-1 Proteins 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- 125000006574 non-aromatic ring group Chemical group 0.000 description 3
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 3
- 239000003505 polymerization initiator Substances 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 125000003107 substituted aryl group Chemical group 0.000 description 3
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 description 3
- 239000001618 (3R)-3-methylpentan-1-ol Substances 0.000 description 2
- QEGNUYASOUJEHD-UHFFFAOYSA-N 1,1-dimethylcyclohexane Chemical compound CC1(C)CCCCC1 QEGNUYASOUJEHD-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- POEDHWVTLBLWDA-UHFFFAOYSA-N 1-butylindole-2,3-dione Chemical compound C1=CC=C2N(CCCC)C(=O)C(=O)C2=C1 POEDHWVTLBLWDA-UHFFFAOYSA-N 0.000 description 2
- BPIUIOXAFBGMNB-UHFFFAOYSA-N 1-hexoxyhexane Chemical compound CCCCCCOCCCCCC BPIUIOXAFBGMNB-UHFFFAOYSA-N 0.000 description 2
- CTMHWPIWNRWQEG-UHFFFAOYSA-N 1-methylcyclohexene Chemical compound CC1=CCCCC1 CTMHWPIWNRWQEG-UHFFFAOYSA-N 0.000 description 2
- AOPDRZXCEAKHHW-UHFFFAOYSA-N 1-pentoxypentane Chemical compound CCCCCOCCCCC AOPDRZXCEAKHHW-UHFFFAOYSA-N 0.000 description 2
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 2
- FZXRXKLUIMKDEL-UHFFFAOYSA-N 2-Methylpropyl propanoate Chemical compound CCC(=O)OCC(C)C FZXRXKLUIMKDEL-UHFFFAOYSA-N 0.000 description 2
- HHBZZTKMMLDNDN-UHFFFAOYSA-N 2-butan-2-yloxybutane Chemical compound CCC(C)OC(C)CC HHBZZTKMMLDNDN-UHFFFAOYSA-N 0.000 description 2
- TZYRSLHNPKPEFV-UHFFFAOYSA-N 2-ethyl-1-butanol Chemical compound CCC(CC)CO TZYRSLHNPKPEFV-UHFFFAOYSA-N 0.000 description 2
- UVEFRWMGQRNNDB-UHFFFAOYSA-N 2-pentan-2-yloxypentane Chemical compound CCCC(C)OC(C)CCC UVEFRWMGQRNNDB-UHFFFAOYSA-N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- DUXCSEISVMREAX-UHFFFAOYSA-N 3,3-dimethylbutan-1-ol Chemical compound CC(C)(C)CCO DUXCSEISVMREAX-UHFFFAOYSA-N 0.000 description 2
- ZCFOBLITZWHNNC-UHFFFAOYSA-N 3-Octen-2-one Natural products CCCCC=CC(C)=O ZCFOBLITZWHNNC-UHFFFAOYSA-N 0.000 description 2
- SHOJXDKTYKFBRD-UHFFFAOYSA-N 4-Methyl-3-penten-2-one, 9CI Chemical compound CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 2
- AQZGPSLYZOOYQP-UHFFFAOYSA-N Diisoamyl ether Chemical compound CC(C)CCOCCC(C)C AQZGPSLYZOOYQP-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- ZOIRKXLFEHOVER-UHFFFAOYSA-N Isopropyl 3-methylbutanoate Chemical compound CC(C)CC(=O)OC(C)C ZOIRKXLFEHOVER-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 229910004541 SiN Inorganic materials 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 150000001345 alkine derivatives Chemical class 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N alpha-methacrylic acid Natural products CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000003849 aromatic solvent Substances 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000005355 arylox oalkyl group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- FUWUEFKEXZQKKA-UHFFFAOYSA-N beta-thujaplicin Chemical compound CC(C)C=1C=CC=C(O)C(=O)C=1 FUWUEFKEXZQKKA-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 2
- 125000002704 decyl group Chemical group [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])* 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- QWHNJUXXYKPLQM-UHFFFAOYSA-N dimethyl cyclopentane Natural products CC1(C)CCCC1 QWHNJUXXYKPLQM-UHFFFAOYSA-N 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 238000005530 etching Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 125000006038 hexenyl group Chemical group 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- ZQMHJBXHRFJKOT-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N=NC(C)(C)C(=O)OC ZQMHJBXHRFJKOT-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 238000000059 patterning Methods 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 2
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 229910052814 silicon oxide Inorganic materials 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- MDYOLVRUBBJPFM-UHFFFAOYSA-N tropolone Chemical compound OC1=CC=CC=CC1=O MDYOLVRUBBJPFM-UHFFFAOYSA-N 0.000 description 2
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
- IEYLGELMIWOKIN-UHFFFAOYSA-N (1-tert-butylcyclopentyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1(C(C)(C)C)CCCC1 IEYLGELMIWOKIN-UHFFFAOYSA-N 0.000 description 1
- QSUJHKWXLIQKEY-UHFFFAOYSA-N (2-oxooxolan-3-yl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCOC1=O QSUJHKWXLIQKEY-UHFFFAOYSA-N 0.000 description 1
- KBSFOAUXMZPTDU-ACCUITESSA-N (2e)-2-(2-ethylhexylidene)cyclohexan-1-one Chemical compound CCCCC(CC)\C=C1/CCCCC1=O KBSFOAUXMZPTDU-ACCUITESSA-N 0.000 description 1
- BSUKKOMNQGNSGP-QPJJXVBHSA-N (2e)-2-ethylidenehexanoic acid Chemical compound CCCC\C(=C/C)C(O)=O BSUKKOMNQGNSGP-QPJJXVBHSA-N 0.000 description 1
- XHZSXTQKJBTXME-GQCTYLIASA-N (2e)-2-ethylidenepentanoic acid Chemical compound CCC\C(=C/C)C(O)=O XHZSXTQKJBTXME-GQCTYLIASA-N 0.000 description 1
- HDKLIZDXVUCLHQ-BQYQJAHWSA-N (3E)-3-nonen-2-one Chemical compound CCCCC\C=C\C(C)=O HDKLIZDXVUCLHQ-BQYQJAHWSA-N 0.000 description 1
- LABTWGUMFABVFG-ONEGZZNKSA-N (3E)-pent-3-en-2-one Chemical compound C\C=C\C(C)=O LABTWGUMFABVFG-ONEGZZNKSA-N 0.000 description 1
- HDKLIZDXVUCLHQ-UHFFFAOYSA-N (E)-3-Nonen-2-one Natural products CCCCCC=CC(C)=O HDKLIZDXVUCLHQ-UHFFFAOYSA-N 0.000 description 1
- 239000001178 (E)-dec-3-en-2-one Substances 0.000 description 1
- 239000001764 (E)-oct-3-en-2-one Substances 0.000 description 1
- KFSQJVOLYQRELE-HWKANZROSA-N (e)-2-ethylbut-2-enoic acid Chemical compound CC\C(=C/C)C(O)=O KFSQJVOLYQRELE-HWKANZROSA-N 0.000 description 1
- ZAMCMCQRTZKGDX-SNAWJCMRSA-N (e)-3-methylpent-3-en-2-one Chemical compound C\C=C(/C)C(C)=O ZAMCMCQRTZKGDX-SNAWJCMRSA-N 0.000 description 1
- JRPDANVNRUIUAB-CMDGGOBGSA-N (e)-dec-3-en-2-one Chemical compound CCCCCC\C=C\C(C)=O JRPDANVNRUIUAB-CMDGGOBGSA-N 0.000 description 1
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1 -dodecene Natural products CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
- LEEANUDEDHYDTG-UHFFFAOYSA-N 1,2-dimethoxypropane Chemical compound COCC(C)OC LEEANUDEDHYDTG-UHFFFAOYSA-N 0.000 description 1
- TXNWMICHNKMOBR-UHFFFAOYSA-N 1,2-dimethylcyclohexene Chemical compound CC1=C(C)CCCC1 TXNWMICHNKMOBR-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 229940005561 1,4-benzoquinone Drugs 0.000 description 1
- SLNPSLWTEUJUGY-UHFFFAOYSA-N 1-(cyclopenten-1-yl)ethanone Chemical compound CC(=O)C1=CCCC1 SLNPSLWTEUJUGY-UHFFFAOYSA-N 0.000 description 1
- LIPRQQHINVWJCH-UHFFFAOYSA-N 1-ethoxypropan-2-yl acetate Chemical compound CCOCC(C)OC(C)=O LIPRQQHINVWJCH-UHFFFAOYSA-N 0.000 description 1
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- CGHIBGNXEGJPQZ-UHFFFAOYSA-N 1-hexyne Chemical compound CCCCC#C CGHIBGNXEGJPQZ-UHFFFAOYSA-N 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- LABTWGUMFABVFG-UHFFFAOYSA-N 1-propenyl methyl ketone Natural products CC=CC(C)=O LABTWGUMFABVFG-UHFFFAOYSA-N 0.000 description 1
- GQCZPFJGIXHZMB-UHFFFAOYSA-N 1-tert-Butoxy-2-propanol Chemical compound CC(O)COC(C)(C)C GQCZPFJGIXHZMB-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- TXVAOITYBBWKMG-HWKANZROSA-N 2-hepten-4-one Chemical compound CCCC(=O)\C=C\C TXVAOITYBBWKMG-HWKANZROSA-N 0.000 description 1
- KPEWEFZCRAOPHV-GQCTYLIASA-N 2-isopropyl trans-crotonic acid Chemical compound C\C=C(/C(C)C)C(O)=O KPEWEFZCRAOPHV-GQCTYLIASA-N 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- YBDQLHBVNXARAU-UHFFFAOYSA-N 2-methyloxane Chemical compound CC1CCCCO1 YBDQLHBVNXARAU-UHFFFAOYSA-N 0.000 description 1
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical compound O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 description 1
- NECRQCBKTGZNMH-UHFFFAOYSA-N 3,5-dimethylhex-1-yn-3-ol Chemical compound CC(C)CC(C)(O)C#C NECRQCBKTGZNMH-UHFFFAOYSA-N 0.000 description 1
- JHHZQADGLDKIPM-AATRIKPKSA-N 3-Hepten-2-one Chemical compound CCC\C=C\C(C)=O JHHZQADGLDKIPM-AATRIKPKSA-N 0.000 description 1
- ZGHFDIIVVIFNPS-UHFFFAOYSA-N 3-Methyl-3-buten-2-one Chemical compound CC(=C)C(C)=O ZGHFDIIVVIFNPS-UHFFFAOYSA-N 0.000 description 1
- ZCFOBLITZWHNNC-VOTSOKGWSA-N 3-Octen-2-one Chemical compound CCCC\C=C\C(C)=O ZCFOBLITZWHNNC-VOTSOKGWSA-N 0.000 description 1
- JSGVZVOGOQILFM-UHFFFAOYSA-N 3-methoxy-1-butanol Chemical compound COC(C)CCO JSGVZVOGOQILFM-UHFFFAOYSA-N 0.000 description 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- KNLXBOKBOCQJTG-UHFFFAOYSA-N 3-methyl-3-(2,2,2-trifluoroethoxymethyl)oxetane Chemical compound FC(F)(F)COCC1(C)COC1 KNLXBOKBOCQJTG-UHFFFAOYSA-N 0.000 description 1
- YYPNJNDODFVZLE-UHFFFAOYSA-N 3-methylbut-2-enoic acid Chemical compound CC(C)=CC(O)=O YYPNJNDODFVZLE-UHFFFAOYSA-N 0.000 description 1
- GYWYASONLSQZBB-UHFFFAOYSA-N 3-methylhexan-2-one Chemical compound CCCC(C)C(C)=O GYWYASONLSQZBB-UHFFFAOYSA-N 0.000 description 1
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 1
- ZAMCMCQRTZKGDX-UHFFFAOYSA-N 3-methylpent-3-en-2-one Natural products CC=C(C)C(C)=O ZAMCMCQRTZKGDX-UHFFFAOYSA-N 0.000 description 1
- FRMKAKWKXLDSSR-FNORWQNLSA-N 3-nonen-5-one Chemical compound CCCCC(=O)\C=C\CC FRMKAKWKXLDSSR-FNORWQNLSA-N 0.000 description 1
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- GXVDVJQTXFTVMP-UHFFFAOYSA-N 4-methoxypentan-2-ol Chemical compound COC(C)CC(C)O GXVDVJQTXFTVMP-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- LLBDJQVIOHGYKX-UHFFFAOYSA-N 5-ethyl-6-methylhept-2-en-4-one Chemical compound CCC(C(C)C)C(=O)C=CC LLBDJQVIOHGYKX-UHFFFAOYSA-N 0.000 description 1
- IYMKNYVCXUEFJE-UHFFFAOYSA-N 5-methylhex-3-en-2-one Chemical compound CC(C)C=CC(C)=O IYMKNYVCXUEFJE-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- PQMMXQYOPUIEJR-UHFFFAOYSA-N C(=O)OCC1=CC=CC=C1.C1(=CC=CC=C1)CC(=O)OC Chemical compound C(=O)OCC1=CC=CC=C1.C1(=CC=CC=C1)CC(=O)OC PQMMXQYOPUIEJR-UHFFFAOYSA-N 0.000 description 1
- MTVGYXAZHAXPSA-UHFFFAOYSA-N CCC(C(F)(F)F)(C(F)(F)F)[U]C(C(CC1C2)C2C2C1C1C=CC2C1)=[U] Chemical compound CCC(C(F)(F)F)(C(F)(F)F)[U]C(C(CC1C2)C2C2C1C1C=CC2C1)=[U] MTVGYXAZHAXPSA-UHFFFAOYSA-N 0.000 description 1
- CZPUVAIKILOSNG-UHFFFAOYSA-N CCC(C1[IH]N1)(C([U]c(c1ccccc1cc1)c1O)=O)[Rh] Chemical compound CCC(C1[IH]N1)(C([U]c(c1ccccc1cc1)c1O)=O)[Rh] CZPUVAIKILOSNG-UHFFFAOYSA-N 0.000 description 1
- ZLNHBTQQJNXGKT-UHFFFAOYSA-N CCC(C1[IH]N1)(C([U]c1cc(O)cc2ccccc12)=O)[Rh] Chemical compound CCC(C1[IH]N1)(C([U]c1cc(O)cc2ccccc12)=O)[Rh] ZLNHBTQQJNXGKT-UHFFFAOYSA-N 0.000 description 1
- FMRIFQHOASMCGA-UHFFFAOYSA-N CCC(CC)(C([U]CC[U]c1c(cccc2O)c2ccc1)=O)[Rh] Chemical compound CCC(CC)(C([U]CC[U]c1c(cccc2O)c2ccc1)=O)[Rh] FMRIFQHOASMCGA-UHFFFAOYSA-N 0.000 description 1
- NYTUIRRXHQHICW-UHFFFAOYSA-N CCC(CC)(C([U]c(c1c2)cccc1ccc2O)=O)[Rh] Chemical compound CCC(CC)(C([U]c(c1c2)cccc1ccc2O)=O)[Rh] NYTUIRRXHQHICW-UHFFFAOYSA-N 0.000 description 1
- XHUUNDVMGNAIGV-UHFFFAOYSA-N CCOC(C(C)(C)CC1)C11CCCCC1 Chemical compound CCOC(C(C)(C)CC1)C11CCCCC1 XHUUNDVMGNAIGV-UHFFFAOYSA-N 0.000 description 1
- BWICMYQEOXPUIV-UHFFFAOYSA-N CCOC1C(C)(C)C2CCC1CC2 Chemical compound CCOC1C(C)(C)C2CCC1CC2 BWICMYQEOXPUIV-UHFFFAOYSA-N 0.000 description 1
- RNRWRHJSZBYQBV-UHFFFAOYSA-N CCOC1C(C)(C)CCC11CC1 Chemical compound CCOC1C(C)(C)CCC11CC1 RNRWRHJSZBYQBV-UHFFFAOYSA-N 0.000 description 1
- DQUZUPFDDIEHPS-UHFFFAOYSA-N CCOC1C2(CCCC2)CCC1(C)C Chemical compound CCOC1C2(CCCC2)CCC1(C)C DQUZUPFDDIEHPS-UHFFFAOYSA-N 0.000 description 1
- GRTDLQBCFBELKE-UHFFFAOYSA-N CCOCC1(C)C(CCC2)C2CC1 Chemical compound CCOCC1(C)C(CCC2)C2CC1 GRTDLQBCFBELKE-UHFFFAOYSA-N 0.000 description 1
- VOQVDNANTIYNMF-UHFFFAOYSA-N CCOCC1(C)C(CCCC2)C2CCC1 Chemical compound CCOCC1(C)C(CCCC2)C2CCC1 VOQVDNANTIYNMF-UHFFFAOYSA-N 0.000 description 1
- RJEWCEPOARLNNQ-UHFFFAOYSA-N CCOCC1(C)CC(CCC2)C2C1 Chemical compound CCOCC1(C)CC(CCC2)C2C1 RJEWCEPOARLNNQ-UHFFFAOYSA-N 0.000 description 1
- VQJBKUHAVVXRFQ-UHFFFAOYSA-N CCOCC1(C)CC(CCCC2)C2CC1 Chemical compound CCOCC1(C)CC(CCCC2)C2CC1 VQJBKUHAVVXRFQ-UHFFFAOYSA-N 0.000 description 1
- WWOBEQRQQQOMEM-UHFFFAOYSA-N CC[U]C1C2(C)CC(C)(C)C1CC2 Chemical compound CC[U]C1C2(C)CC(C)(C)C1CC2 WWOBEQRQQQOMEM-UHFFFAOYSA-N 0.000 description 1
- BLFWFUOPZDUPNA-UHFFFAOYSA-N CC[U]C1C2CCC1CC2 Chemical compound CC[U]C1C2CCC1CC2 BLFWFUOPZDUPNA-UHFFFAOYSA-N 0.000 description 1
- BZPLHQSBKAPRAL-UHFFFAOYSA-N COCC[U]c(cc1)c(cccc2)c2c1[S+]1CCCC1 Chemical compound COCC[U]c(cc1)c(cccc2)c2c1[S+]1CCCC1 BZPLHQSBKAPRAL-UHFFFAOYSA-N 0.000 description 1
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- XXRCUYVCPSWGCC-UHFFFAOYSA-N Ethyl pyruvate Chemical compound CCOC(=O)C(C)=O XXRCUYVCPSWGCC-UHFFFAOYSA-N 0.000 description 1
- OUGPMNMLWKSBRI-UHFFFAOYSA-N Hexyl formate Chemical compound CCCCCCOC=O OUGPMNMLWKSBRI-UHFFFAOYSA-N 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 229910016006 MoSi Inorganic materials 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- DNWPWJYXPGOCCN-UHFFFAOYSA-N OC(C(=O)OCC)(C)C.OC(C(=O)OC)(C)C Chemical compound OC(C(=O)OCC)(C)C.OC(C(=O)OC)(C)C DNWPWJYXPGOCCN-UHFFFAOYSA-N 0.000 description 1
- VRVHHLYUCAIGJG-UHFFFAOYSA-N OS(CC(C(F)(F)F)(C(F)(F)F)[U]C(C1CCCCC1)=[U])(=O)=O Chemical compound OS(CC(C(F)(F)F)(C(F)(F)F)[U]C(C1CCCCC1)=[U])(=O)=O VRVHHLYUCAIGJG-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 239000007877 V-601 Substances 0.000 description 1
- VJMAITQRABEEKP-UHFFFAOYSA-N [6-(phenylmethoxymethyl)-1,4-dioxan-2-yl]methyl acetate Chemical class O1C(COC(=O)C)COCC1COCC1=CC=CC=C1 VJMAITQRABEEKP-UHFFFAOYSA-N 0.000 description 1
- 229940022663 acetate Drugs 0.000 description 1
- 125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- HVBNWICGKWTLIY-UHFFFAOYSA-N adamantan-1-ol;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.C1C(C2)CC3CC2CC1(O)C3 HVBNWICGKWTLIY-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000004849 alkoxymethyl group Chemical group 0.000 description 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- TUFYVOCKVJOUIR-UHFFFAOYSA-N alpha-Thujaplicin Natural products CC(C)C=1C=CC=CC(=O)C=1O TUFYVOCKVJOUIR-UHFFFAOYSA-N 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000005380 borophosphosilicate glass Substances 0.000 description 1
- NYWSOZIZKAROHJ-UHFFFAOYSA-N c(cc1)ccc1[S+]1c2ccccc2Sc2c1cccc2 Chemical compound c(cc1)ccc1[S+]1c2ccccc2Sc2c1cccc2 NYWSOZIZKAROHJ-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 235000005513 chalcones Nutrition 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- WZCRDVTWUYLPTR-UHFFFAOYSA-N cyclohept-2-en-1-one Chemical compound O=C1CCCCC=C1 WZCRDVTWUYLPTR-UHFFFAOYSA-N 0.000 description 1
- ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 description 1
- GPTJTTCOVDDHER-UHFFFAOYSA-N cyclononane Chemical compound C1CCCCCCCC1 GPTJTTCOVDDHER-UHFFFAOYSA-N 0.000 description 1
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 1
- 239000004914 cyclooctane Substances 0.000 description 1
- URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 description 1
- 239000004913 cyclooctene Substances 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- DIOQZVSQGTUSAI-NJFSPNSNSA-N decane Chemical compound CCCCCCCCC[14CH3] DIOQZVSQGTUSAI-NJFSPNSNSA-N 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- CSYSRRCOBYEGPI-UHFFFAOYSA-N diazo(sulfonyl)methane Chemical compound [N-]=[N+]=C=S(=O)=O CSYSRRCOBYEGPI-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- ZWWQRMFIZFPUAA-UHFFFAOYSA-N dimethyl 2-methylidenebutanedioate Chemical compound COC(=O)CC(=C)C(=O)OC ZWWQRMFIZFPUAA-UHFFFAOYSA-N 0.000 description 1
- LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical compound COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 229940069096 dodecene Drugs 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229940117360 ethyl pyruvate Drugs 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000001530 fumaric acid Substances 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
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 229930002839 ionone Natural products 0.000 description 1
- 150000002499 ionone derivatives Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- IMXBRVLCKXGWSS-UHFFFAOYSA-N methyl 2-cyclohexylacetate Chemical compound COC(=O)CC1CCCCC1 IMXBRVLCKXGWSS-UHFFFAOYSA-N 0.000 description 1
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- 150000002848 norbornenes Chemical class 0.000 description 1
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical group C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 150000002921 oxetanes Chemical group 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 230000010363 phase shift Effects 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007152 ring opening metathesis polymerisation reaction Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
- YBDQLHBVNXARAU-ZCFIWIBFSA-N tetrahydro-2-methyl-2H-pyran Natural products C[C@@H]1CCCCO1 YBDQLHBVNXARAU-ZCFIWIBFSA-N 0.000 description 1
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- BWHOZHOGCMHOBV-BQYQJAHWSA-N trans-benzylideneacetone Chemical compound CC(=O)\C=C\C1=CC=CC=C1 BWHOZHOGCMHOBV-BQYQJAHWSA-N 0.000 description 1
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- JHHZQADGLDKIPM-UHFFFAOYSA-N trans-hept-3-en-2-one Natural products CCCC=CC(C)=O JHHZQADGLDKIPM-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- VSRBKQFNFZQRBM-UHFFFAOYSA-N tuaminoheptane Chemical compound CCCCCC(C)N VSRBKQFNFZQRBM-UHFFFAOYSA-N 0.000 description 1
- 229960003986 tuaminoheptane Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229930007845 β-thujaplicin Natural products 0.000 description 1
Images
Classifications
-
- 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
-
- 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
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
- G03F7/0397—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition the macromolecular compound having an alicyclic moiety in a side chain
-
- 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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/30—Imagewise removal using liquid means
- G03F7/32—Liquid compositions therefor, e.g. developers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
- C08L33/08—Homopolymers or copolymers of acrylic acid esters
-
- 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
- G03F7/0046—Photosensitive materials with perfluoro compounds, e.g. for dry lithography
-
- 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
- G03F7/0048—Photosensitive materials characterised by the solvents or agents facilitating spreading, e.g. tensio-active agents
-
- 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
- G03F7/0382—Macromolecular compounds which are rendered insoluble or differentially wettable the macromolecular compound being present in a chemically amplified negative photoresist composition
-
- 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
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
-
- 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
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers
-
- 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
- G03F7/16—Coating processes; Apparatus therefor
- G03F7/168—Finishing the coated layer, e.g. drying, baking, soaking
-
- 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
- G03F7/20—Exposure; Apparatus therefor
- G03F7/2041—Exposure; Apparatus therefor in the presence of a fluid, e.g. immersion; using fluid cooling means
-
- 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
- G03F7/20—Exposure; Apparatus therefor
- G03F7/2051—Exposure without an original mask, e.g. using a programmed deflection of a point source, by scanning, by drawing with a light beam, using an addressed light or corpuscular source
- G03F7/2059—Exposure without an original mask, e.g. using a programmed deflection of a point source, by scanning, by drawing with a light beam, using an addressed light or corpuscular source using a scanning corpuscular radiation beam, e.g. an electron beam
-
- 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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/30—Imagewise removal using liquid means
- G03F7/32—Liquid compositions therefor, e.g. developers
- G03F7/325—Non-aqueous compositions
-
- 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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/38—Treatment before imagewise removal, e.g. prebaking
-
- 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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/40—Treatment after imagewise removal, e.g. baking
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Structural Engineering (AREA)
- Toxicology (AREA)
- Architecture (AREA)
- Engineering & Computer Science (AREA)
- Materials For Photolithography (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Optics & Photonics (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
Abstract
【解決手段】(A)下記式(1)で表される化合物、(B)所定の繰り返し単位を含み、酸の作用により有機溶剤含有現像液に対する溶解度が変化する樹脂、及び(C)光酸発生剤を含むレジスト組成物。
(式中、R1〜R4は、それぞれ独立に、水素原子、ヒドロキシ基、又はヘテロ原子を含んでいてもよい炭素数1〜20の直鎖状、分岐状若しくは環状の1価炭化水素基を表す。R1〜R4は、互いに結合してこれらが結合する炭素原子とそれらの間の炭素原子と共に環を形成してもよい。)
【選択図】なし
Description
1.(A)下記式(1)で表される化合物、
(B)下記式(2)で表される繰り返し単位及び下記式(3)で表される繰り返し単位を含み、酸の作用により有機溶剤含有現像液に対する溶解度が変化する樹脂、及び
(C)光酸発生剤
を含むことを特徴とするレジスト組成物。
2.(C)光酸発生剤が、下記式(4)又は(5)で表されるものである1のレジスト組成物。
M+ X- (4)
(式中、M+は、下記式(4a)で表されるスルホニウムカチオン又は下記式(4b)で表されるヨードニウムカチオンを表す。X-は、下記式(4c)〜(4f)から選ばれるアニオンを表す。)
3.更に、(D)有機溶剤を含む1又は2のレジスト組成物。
4.更に、(E)含フッ素疎水性樹脂を含む1〜3のいずれかのレジスト組成物。
5.更に、(F)下記式(6a)、(6b)及び(6c)から選ばれる化合物を少なくとも1種以上含む1〜4のいずれかのレジスト組成物。
6.更に、第1級、第2級及び第3級の脂肪族アミン類、混成アミン類、芳香族アミン類、複素環アミン類、カルボキシル基を有する含窒素化合物、スルホニル基を有する含窒素化合物、ヒドロキシ基を有する含窒素化合物、ヒドロキシフェニル基を有する含窒素化合物、アルコール性含窒素化合物、アミド誘導体、並びにイミド誘導体から選ばれる1種以上の塩基性化合物を含む1〜5のいずれかのレジスト組成物。
7.1〜6のいずれかの化学増幅型レジスト組成物を基板上に塗布する工程、
加熱処理後ArFエキシマレーザー、電子線又は極端紫外線で露光する工程、及び
加熱処理した後、現像液を用いて現像する工程
を含むことを特徴とするパターン形成方法。
8.前記露光が、屈折率1.0以上の液体をレジスト塗布膜と投影レンズとの間に介在させて行う液浸露光である7のパターン形成方法。
9.前記レジスト塗布膜の上に更に保護膜を塗布し、該保護膜と投影レンズとの間に前記液体を介在させて液浸露光を行う8のパターン形成方法。
10.前記現像液が有機溶剤を含むものであり、現像によってネガティブパターンを形成する7〜9のいずれかのパターン形成方法。
11.前記有機溶剤が、2−オクタノン、3−オクタノン、4−オクタノン、2−ノナノン、3−ノナノン、4−ノナノン、5−ノナノン、2−ヘプタノン、3−ヘプタノン、4−ヘプタノン、2−ヘキサノン、3−ヘキサノン、ジイソブチルケトン、2−メチルシクロヘキサノン、3−メチルシクロヘキサノン、4−メチルシクロヘキサノン、2−エチルシクロヘキサノン、3−エチルシクロヘキサノン、4−エチルシクロヘキサノン、アセトフェノン、2'−メチルアセトフェノン、4'−メチルアセトフェノン、2'−エチルアセトフェノン、4'−エチルアセトフェノン、エチル−n−ブチルケトン、ジ−n−ブチルケトン、酢酸プロピル、酢酸ブチル、酢酸イソブチル、酢酸ペンチル、酢酸ブテニル、酢酸イソペンチル、酢酸フェニル、ギ酸プロピル、ギ酸ブチル、ギ酸イソブチル、ギ酸ペンチル、ギ酸イソペンチル、吉草酸メチル、ペンテン酸メチル、クロトン酸メチル、クロトン酸エチル、プロピオン酸メチル、プロピオン酸エチル、3−エトキシプロピオン酸エチル、乳酸メチル、乳酸エチル、乳酸プロピル、乳酸ブチル、乳酸イソブチル、乳酸ペンチル、乳酸イソペンチル、2−ヒドロキシイソ酪酸メチル、2−ヒドロキシイソ酪酸エチル、安息香酸メチル、安息香酸エチル、酢酸ベンジル、フェニル酢酸メチル、ギ酸ベンジル、ギ酸フェニルエチル、3−フェニルプロピオン酸メチル、プロピオン酸ベンジル、フェニル酢酸エチル、酢酸2−フェニルエチル、酢酸2−メチルブチル、酢酸ヘキシル、酢酸2−エチルヘキシル、酢酸シクロヘキシル、酢酸メチルシクロヘキシル、ギ酸ヘキシル、吉草酸エチル、吉草酸プロピル、吉草酸イソプロピル、吉草酸ブチル、吉草酸イソブチル、吉草酸t−ブチル、吉草酸ペンチル、吉草酸イソペンチル、イソ吉草酸エチル、イソ吉草酸プロピル、イソ吉草酸イソプロピル、イソ吉草酸ブチル、イソ吉草酸イソブチル、イソ吉草酸t−ブチル、イソ吉草酸イソペンチル、2−メチル吉草酸エチル、2−メチル吉草酸ブチル、ピバル酸エチル、ピバル酸プロピル、ピバル酸イソプロピル、ピバル酸ブチル、ピバル酸t−ブチル、ペンテン酸エチル、ペンテン酸プロピル、ペンテン酸イソプロピル、ペンテン酸ブチル、ペンテン酸t−ブチル、クロトン酸プロピル、クロトン酸イソプロピル、クロトン酸ブチル、クロトン酸t−ブチル、プロピオン酸ブチル、プロピオン酸イソブチル、プロピオン酸t−ブチル、ヘキサン酸エチル、ヘキサン酸アリル、ヘキサンアリル、酪酸プロピル、酪酸ブチル、酪酸イソブチル、酪酸3−メチルブチル、酪酸t−ブチル、2−メチル酪酸エチル、2−メチル酪酸イソプロピル、安息香酸プロピル、安息香酸ブチル、1−ブチルアルコール、2−ブチルアルコール、イソブチルアルコール、t−ブチルアルコール、1−ペンタノール、2−ペンタノール、3−ペンタノール、t−ペンチルアルコール、ネオペンチルアルコール、2−メチル−1−ブタノール、3−メチル−1−ブタノール、3−メチル−3−ペンタノール、シクロペンタノール、1−ヘキサノール、2−ヘキサノール、3−ヘキサノール、2,3−ジメチル−2−ブタノール、3,3−ジメチル−1−ブタノール、3,3−ジメチル−2−ブタノール、2,2−ジエチル−1−ブタノール、2−メチル−1−ペンタノール、2−メチル−2−ペンタノール、2−メチル−3−ペンタノール、3−メチル−1−ペンタノール、3−メチル−2−ペンタノール、4−メチル−1−ペンタノール、4−メチル−2−ペンタノール、4−メチル−3−ペンタノール、シクロヘキサノール及び1−オクタノールから選ばれる1種以上である10のパターン形成方法。
本発明のレジスト組成物は、(B)下記式(2)で表される繰り返し単位及び下記式(3)で表される繰り返し単位を含み、酸の作用により有機溶剤含有現像液に対する溶解度が変化する樹脂(ベース樹脂)を含む。
(I)式(2)で表される繰り返し単位の1種又は2種以上を、好ましくは1モル%以上60モル%以下、より好ましくは5〜50モル%、更に好ましくは10〜50モル%、
(II)式(3)で表される繰り返し単位の1種又は2種以上を、好ましくは40〜99モル%、より好ましくは50〜95モル%、更により好ましくは50〜90モル%、
(III)式(d1)又は(d2)で表される繰り返し単位の1種又は2種以上を、好ましくは0〜30モル%、より好ましくは0〜20モル%、更に好ましくは0〜10モル%、及び
(IV)その他の単量体に由来する繰り返し単位の1種又は2種以上を、好ましくは0〜80モル%、より好ましくは0〜70モル%、更に好ましくは0〜50モル%。
本発明のレジスト組成物は、(D)有機溶剤を含んでもよい。前記有機溶剤としては、ベース樹脂、光酸発生剤、酸拡散制御剤(クエンチャー)、その他の添加剤等が溶解可能なものであれば特に限定されない。このような有機溶剤としては、例えば、特開2008−111103号公報の段落[0144]〜[0145]に記載のシクロヘキサノン、メチル−2−n−ペンチルケトン等のケトン類;3−メトキシブタノール、3−メチル−3−メトキシブタノール、1−メトキシ−2−プロパノール、1−エトキシ−2−プロパノール等のアルコール類;プロピレングリコールモノメチルエーテル、エチレングリコールモノメチルエーテル、プロピレングリコールモノエチルエーテル、エチレングリコールモノエチルエーテル、プロピレングリコールジメチルエーテル、ジエチレングリコールジメチルエーテル等のエーテル類;プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールモノエチルエーテルアセテート、乳酸エチル、ピルビン酸エチル、酢酸ブチル、3−メトキシプロピオン酸メチル、3−エトキシプロピオン酸エチル、酢酸t−ブチル、プロピオン酸t−ブチル、プロピレングリコールモノt−ブチルエーテルアセテート等のエステル類;γ−ブチロラクトン等のラクトン類、及びこれらの混合溶剤が挙げられる。アセタール系の酸不安定基を用いる場合は、アセタールの脱保護反応を加速させるために高沸点のアルコール系溶剤、具体的にはジエチレングリコール、プロピレングリコール、グリセリン、1,4−ブタンジオール、1,3−ブタンジオール等を加えることもできる。
本発明のレジスト組成物は、(E)含フッ素疎水性樹脂を含んでもよい。前記含フッ素疎水性樹脂は、水に不溶又は難溶で現像液に可溶な界面活性剤であり、ArF液浸露光においてレジスト保護膜を用いない場合、スピンコート後のレジスト表面に配向することによって水のしみ込みやリーチングを低減させる機能を有する。そのため、レジスト膜からの水溶性成分の溶出を抑えて露光装置へのダメージを下げるために有用であり、また、露光後、ポストベーク後の現像で溶解し、欠陥の原因となる異物にもなり難いため有用である。前記含フッ素疎水性樹脂としては、特に撥水性が高く滑水性を向上させるものが好ましい。
本発明のレジスト組成物は、(G)含窒素非イオン性化合物を含んでもよい。前記含窒素非イオン性化合物としては、第1級、第2級又は第3級脂肪族アミン類、混成アミン類、芳香族アミン類、複素環アミン類、カルボキシル基を有する含窒素化合物、スルホニル基を有する含窒素化合物、ヒドロキシ基を有する含窒素化合物、ヒドロキシフェニル基を有する含窒素化合物、アルコール性含窒素化合物、アミド誘導体、イミド誘導体等が挙げられる。前記含窒素非イオン性化合物としては、特開2008−111103号公報の段落[0146]〜[0164]に記載のものを使用することができる。
本発明のレジスト組成物は、(H)界面活性剤を含んでもよい。前記界面活性剤としては、特開2011−16746号公報に記載のものを参照することができる。これらのうち。水及びアルカリ現像液に不溶又は難溶な界面活性剤が好ましい。
本発明のレジスト組成物は、その他の成分として、酸増殖化合物、有機酸誘導体、フッ素置換アルコール、酸の作用により現像液への溶解性が変化する重量平均分子量3,000以下の化合物(溶解阻止剤)等を含んでもよい。前記酸増殖化合物としては、特開2009−269953号公報又は特開2010−215608号公報に記載の化合物を参照できる。前記酸増殖化合物の配合量は、(B)ベース樹脂100質量部に対して0〜2質量部が好ましく、0〜1質量部がより好ましい。添加量が多すぎると拡散の制御が難しく、解像性の劣化、パターン形状の劣化が起こることがある。前記有機酸誘導体、フッ素置換アルコール及び溶解阻止剤としては、特開2009−269953号公報又は特開2010−215608号公報に記載の化合物を参照できる。
本発明は、更に、前述したレジスト組成物を用いたパターン形成方法を提供する。本発明のレジスト組成物を使用してパターンを形成するには、公知のリソグラフィー技術を採用して行うことができる。例えば、本発明のレジスト組成物を基板上に塗布してレジスト膜を形成し、加熱処理後に高エネルギー線をこのレジスト膜の所定の部分に照射、露光し、加熱処理後に有機溶剤含有現像液を用いて前記レジスト膜の未露光部分を溶解し、露光部分が膜として残り、ホールやトレンチパターン等のネガティブトーンのレジストパターンを形成することができる。
[合成例1]ポリマーP−1の合成
窒素雰囲気下、フラスコに、メタクリル酸1−t−ブチルシクロペンチル22g、メタクリル酸2−オキソテトラヒドロフラン−3−イル17g、V−601(和光純薬工業(株)製)0.48g、2−メルカプトエタノール0.41g及びメチルエチルケトン50gをとり、単量体−重合開始剤溶液を調製した。窒素雰囲気とした別のフラスコにメチルエチルケトン23gをとり、攪拌しながら80℃まで加熱した後、前記単量体−重合開始剤溶液を4時間かけて滴下した。滴下終了後、重合溶液の温度を80℃に保ったまま2時間攪拌を続け、次いで室温まで冷却した。得られた重合溶液を、激しく攪拌したメタノール640g中に滴下し、析出した共重合体を濾別した。共重合体をメタノール240gで2回洗浄した後、50℃で20時間真空乾燥して36gの白色粉末状の共重合体を得た(収率90%)。GPCにて分析したところ、Mwは8,755、分散度は1.94であった。
各単量体の種類、配合比を変えた以外は、合成例1と同様の手順により、ポリマーP−2〜P−24を合成した。
[実施例1−1〜1−36、比較例1−1〜1−24]
PPD抑制剤(AA−1〜AA−3)、酸拡散制御剤(Q−1)、ベース樹脂(P−1〜P−24)、光酸発生剤(PAG−X〜PAG−Z)及びアルカリ可溶型界面活性剤(SF−1)を、下記表4〜6に示す組成にて、界面活性剤A(オムノバ社製)0.01質量%を含む溶剤中に溶解してレジスト組成物を調合し、更にレジスト組成物を0.2μmのテフロン(登録商標)製フィルターで濾過することにより、レジスト組成物(R−1〜R−56)を調製した。
GBL:γ−ブチロラクトン
Mw=7,700
分散度=1.82
Mw=1,500
[実施例2−1〜2−36、比較例2−1〜2−24]
レジスト組成物R−1〜R−56を、それぞれ、シリコンウエハーにスピンオンカーボン膜ODL-101(信越化学工業(株)製)を180nm、その上にケイ素含有スピンオンハードマスクSHB-A940(信越化学工業(株)製)を40nmの膜厚で成膜したトライレイヤープロセス用の基板上にスピンコーティングした。次いで、ホットプレートを用いて100℃で60秒間ベークし、レジスト膜の厚みを90nmにした。これをArFエキシマレーザー液浸スキャナー((株)ニコン製、NSR-610C、NA1.30、σ0.90/0.70、アニュラー照明、6%ハーフトーン位相シフトマスク)を用いて、ピッチが150nmで50nmのホールパターンを形成できる露光量で露光し、露光後100℃で60秒間PEBをした。PEB終了後、引き置きせずに(PPD 0 h)、酢酸n−ブチルで30秒間パドル現像してピッチが150nmで50nmのホールパターンを形成したウエハー、及び同条件でPEB終了後、6時間引き置いた(PPD 6 h)後に酢酸n−ブチルで現像したウエハーを作製した。PPD 0hと、PPD 6hのウエハーは、測長SEM((株)日立製作所製CG-4000)で、PPDによるCDシュリンク量とCDバラつきを求めた。結果を表7及び8に示す。
20 被加工層
30 中間介在層
40 レジスト膜
50 露光
Claims (11)
- (A)下記式(1)で表される化合物、
(B)下記式(2)で表される繰り返し単位及び下記式(3)で表される繰り返し単位を含み、酸の作用により有機溶剤含有現像液に対する溶解度が変化する樹脂、及び
(C)光酸発生剤
を含むことを特徴とするレジスト組成物。
- (C)光酸発生剤が、下記式(4)又は(5)で表されるものである請求項1記載のレジスト組成物。
M+ X- (4)
(式中、M+は、下記式(4a)で表されるスルホニウムカチオン又は下記式(4b)で表されるヨードニウムカチオンを表す。X-は、下記式(4c)〜(4f)から選ばれるアニオンを表す。)
- 更に、(D)有機溶剤を含む請求項1又は2記載のレジスト組成物。
- 更に、(E)含フッ素疎水性樹脂を含む請求項1〜3のいずれか1項記載のレジスト組成物。
- 更に、(F)下記式(6a)、(6b)及び(6c)から選ばれる化合物を少なくとも1種以上含む請求項1〜4のいずれか1項記載のレジスト組成物。
- 更に、第1級、第2級及び第3級の脂肪族アミン類、混成アミン類、芳香族アミン類、複素環アミン類、カルボキシル基を有する含窒素化合物、スルホニル基を有する含窒素化合物、ヒドロキシ基を有する含窒素化合物、ヒドロキシフェニル基を有する含窒素化合物、アルコール性含窒素化合物、アミド誘導体、並びにイミド誘導体から選ばれる1種以上の塩基性化合物を含む請求項1〜5のいずれか1項記載のレジスト組成物。
- 請求項1〜6のいずれか1項記載の化学増幅型レジスト組成物を基板上に塗布する工程、
加熱処理後ArFエキシマレーザー、電子線又は極端紫外線で露光する工程、及び
加熱処理した後、現像液を用いて現像する工程
を含むことを特徴とするパターン形成方法。 - 前記露光が、屈折率1.0以上の液体をレジスト塗布膜と投影レンズとの間に介在させて行う液浸露光である請求項7記載のパターン形成方法。
- 前記レジスト塗布膜の上に更に保護膜を塗布し、該保護膜と投影レンズとの間に前記液体を介在させて液浸露光を行う請求項8記載のパターン形成方法。
- 前記現像液が有機溶剤を含むものであり、現像によってネガティブパターンを形成する請求項7〜9のいずれか1項記載のパターン形成方法。
- 前記有機溶剤が、2−オクタノン、3−オクタノン、4−オクタノン、2−ノナノン、3−ノナノン、4−ノナノン、5−ノナノン、2−ヘプタノン、3−ヘプタノン、4−ヘプタノン、2−ヘキサノン、3−ヘキサノン、ジイソブチルケトン、2−メチルシクロヘキサノン、3−メチルシクロヘキサノン、4−メチルシクロヘキサノン、2−エチルシクロヘキサノン、3−エチルシクロヘキサノン、4−エチルシクロヘキサノン、アセトフェノン、2'−メチルアセトフェノン、4'−メチルアセトフェノン、2'−エチルアセトフェノン、4'−エチルアセトフェノン、エチル−n−ブチルケトン、ジ−n−ブチルケトン、酢酸プロピル、酢酸ブチル、酢酸イソブチル、酢酸ペンチル、酢酸ブテニル、酢酸イソペンチル、酢酸フェニル、ギ酸プロピル、ギ酸ブチル、ギ酸イソブチル、ギ酸ペンチル、ギ酸イソペンチル、吉草酸メチル、ペンテン酸メチル、クロトン酸メチル、クロトン酸エチル、プロピオン酸メチル、プロピオン酸エチル、3−エトキシプロピオン酸エチル、乳酸メチル、乳酸エチル、乳酸プロピル、乳酸ブチル、乳酸イソブチル、乳酸ペンチル、乳酸イソペンチル、2−ヒドロキシイソ酪酸メチル、2−ヒドロキシイソ酪酸エチル、安息香酸メチル、安息香酸エチル、酢酸ベンジル、フェニル酢酸メチル、ギ酸ベンジル、ギ酸フェニルエチル、3−フェニルプロピオン酸メチル、プロピオン酸ベンジル、フェニル酢酸エチル、酢酸2−フェニルエチル、酢酸2−メチルブチル、酢酸ヘキシル、酢酸2−エチルヘキシル、酢酸シクロヘキシル、酢酸メチルシクロヘキシル、ギ酸ヘキシル、吉草酸エチル、吉草酸プロピル、吉草酸イソプロピル、吉草酸ブチル、吉草酸イソブチル、吉草酸t−ブチル、吉草酸ペンチル、吉草酸イソペンチル、イソ吉草酸エチル、イソ吉草酸プロピル、イソ吉草酸イソプロピル、イソ吉草酸ブチル、イソ吉草酸イソブチル、イソ吉草酸t−ブチル、イソ吉草酸イソペンチル、2−メチル吉草酸エチル、2−メチル吉草酸ブチル、ピバル酸エチル、ピバル酸プロピル、ピバル酸イソプロピル、ピバル酸ブチル、ピバル酸t−ブチル、ペンテン酸エチル、ペンテン酸プロピル、ペンテン酸イソプロピル、ペンテン酸ブチル、ペンテン酸t−ブチル、クロトン酸プロピル、クロトン酸イソプロピル、クロトン酸ブチル、クロトン酸t−ブチル、プロピオン酸ブチル、プロピオン酸イソブチル、プロピオン酸t−ブチル、ヘキサン酸エチル、ヘキサン酸アリル、ヘキサンアリル、酪酸プロピル、酪酸ブチル、酪酸イソブチル、酪酸3−メチルブチル、酪酸t−ブチル、2−メチル酪酸エチル、2−メチル酪酸イソプロピル、安息香酸プロピル、安息香酸ブチル、1−ブチルアルコール、2−ブチルアルコール、イソブチルアルコール、t−ブチルアルコール、1−ペンタノール、2−ペンタノール、3−ペンタノール、t−ペンチルアルコール、ネオペンチルアルコール、2−メチル−1−ブタノール、3−メチル−1−ブタノール、3−メチル−3−ペンタノール、シクロペンタノール、1−ヘキサノール、2−ヘキサノール、3−ヘキサノール、2,3−ジメチル−2−ブタノール、3,3−ジメチル−1−ブタノール、3,3−ジメチル−2−ブタノール、2,2−ジエチル−1−ブタノール、2−メチル−1−ペンタノール、2−メチル−2−ペンタノール、2−メチル−3−ペンタノール、3−メチル−1−ペンタノール、3−メチル−2−ペンタノール、4−メチル−1−ペンタノール、4−メチル−2−ペンタノール、4−メチル−3−ペンタノール、シクロヘキサノール及び1−オクタノールから選ばれる1種以上である請求項10記載のパターン形成方法。
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2015091338A JP6394481B2 (ja) | 2015-04-28 | 2015-04-28 | レジスト組成物及びパターン形成方法 |
EP16164164.2A EP3088955B1 (en) | 2015-04-28 | 2016-04-07 | Resist composition and patterning process |
TW105112880A TWI614580B (zh) | 2015-04-28 | 2016-04-26 | 光阻組成物及圖案形成方法 |
KR1020160051603A KR102071757B1 (ko) | 2015-04-28 | 2016-04-27 | 레지스트 조성물 및 패턴 형성 방법 |
US15/139,831 US9921479B2 (en) | 2015-04-28 | 2016-04-27 | Resist composition and patterning process |
CN201610272230.2A CN106094450B (zh) | 2015-04-28 | 2016-04-28 | 抗蚀剂组合物和图案化方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2015091338A JP6394481B2 (ja) | 2015-04-28 | 2015-04-28 | レジスト組成物及びパターン形成方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2016206586A true JP2016206586A (ja) | 2016-12-08 |
JP6394481B2 JP6394481B2 (ja) | 2018-09-26 |
Family
ID=55745580
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2015091338A Active JP6394481B2 (ja) | 2015-04-28 | 2015-04-28 | レジスト組成物及びパターン形成方法 |
Country Status (6)
Country | Link |
---|---|
US (1) | US9921479B2 (ja) |
EP (1) | EP3088955B1 (ja) |
JP (1) | JP6394481B2 (ja) |
KR (1) | KR102071757B1 (ja) |
CN (1) | CN106094450B (ja) |
TW (1) | TWI614580B (ja) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110192152A (zh) * | 2017-01-13 | 2019-08-30 | 日产化学株式会社 | 包含酰胺溶剂的抗蚀剂下层膜形成用组合物 |
JPWO2018116915A1 (ja) * | 2016-12-22 | 2019-11-21 | 富士フイルム株式会社 | 感活性光線性又は感放射線性樹脂組成物、感活性光線性又は感放射線性膜、パターン形成方法、及び、電子デバイスの製造方法 |
WO2020044771A1 (ja) * | 2018-08-29 | 2020-03-05 | 富士フイルム株式会社 | 感活性光線性又は感放射線性樹脂組成物、レジスト膜、パターン形成方法、電子デバイスの製造方法 |
WO2020209527A1 (ko) * | 2019-04-09 | 2020-10-15 | 영창케미칼 주식회사 | 고두께 스핀 온 카본 하드마스크 조성물 및 이를 이용한 패턴화 방법 |
JP2021021773A (ja) * | 2019-07-25 | 2021-02-18 | 東京応化工業株式会社 | レジスト組成物及びレジストパターン形成方法 |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10042251B2 (en) * | 2016-09-30 | 2018-08-07 | Rohm And Haas Electronic Materials Llc | Zwitterionic photo-destroyable quenchers |
KR102177417B1 (ko) * | 2017-12-31 | 2020-11-11 | 롬 앤드 하스 일렉트로닉 머트어리얼즈 엘엘씨 | 포토레지스트 조성물 및 방법 |
JP6875325B2 (ja) * | 2018-05-21 | 2021-05-19 | 信越化学工業株式会社 | パターン形成方法 |
JP6933605B2 (ja) * | 2018-05-21 | 2021-09-08 | 信越化学工業株式会社 | パターン形成方法 |
JP6950662B2 (ja) * | 2018-10-30 | 2021-10-13 | 信越化学工業株式会社 | 基板保護膜形成用材料及びパターン形成方法 |
US20210198468A1 (en) * | 2019-12-31 | 2021-07-01 | Taiwan Semiconductor Manufacturing Co., Ltd. | Photoresist composition and method of manufacturing a semiconductor device |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2000250204A (ja) * | 1999-03-04 | 2000-09-14 | Shin Etsu Chem Co Ltd | フォトレジスト材料およびパターン形成方法 |
JP2009515944A (ja) * | 2005-11-16 | 2009-04-16 | エイゼット・エレクトロニック・マテリアルズ・ユーエスエイ・コーポレイション | 光活性化合物 |
JP2010152068A (ja) * | 2008-12-25 | 2010-07-08 | Tokyo Ohka Kogyo Co Ltd | レジスト組成物、およびレジストパターン形成方法 |
WO2012053396A1 (ja) * | 2010-10-19 | 2012-04-26 | Jsr株式会社 | レジストパターン形成方法及び感放射線性樹脂組成物 |
JP2014199389A (ja) * | 2012-07-24 | 2014-10-23 | 富士フイルム株式会社 | 感活性光線性又は感放射線性樹脂組成物、該組成物を用いた感活性光線性又は感放射線性膜及びパターン形成方法、並びに電子デバイスの製造方法及び電子デバイス |
Family Cites Families (53)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5807977A (en) | 1992-07-10 | 1998-09-15 | Aerojet General Corporation | Polymers and prepolymers from mono-substituted fluorinated oxetane monomers |
JP3713808B2 (ja) * | 1996-05-09 | 2005-11-09 | 住友化学株式会社 | フォトレジスト組成物 |
JP2000336121A (ja) | 1998-11-02 | 2000-12-05 | Shin Etsu Chem Co Ltd | 新規なエステル化合物、高分子化合物、レジスト材料、及びパターン形成方法 |
JP4226803B2 (ja) | 2000-08-08 | 2009-02-18 | 富士フイルム株式会社 | ポジ型感光性組成物 |
JP4013044B2 (ja) | 2001-06-15 | 2007-11-28 | 信越化学工業株式会社 | レジスト材料、及びパターン形成方法 |
JP3912767B2 (ja) | 2001-06-21 | 2007-05-09 | 富士フイルム株式会社 | ポジ型感光性組成物 |
JP4162527B2 (ja) | 2003-03-31 | 2008-10-08 | 富士フイルム株式会社 | ポジ型レジスト組成物 |
JP4308051B2 (ja) * | 2004-03-22 | 2009-08-05 | 富士フイルム株式会社 | 感光性組成物及びそれを用いたパターン形成方法 |
JP4816921B2 (ja) | 2005-04-06 | 2011-11-16 | 信越化学工業株式会社 | 新規スルホン酸塩及びその誘導体、光酸発生剤並びにこれを用いたレジスト材料及びパターン形成方法 |
JP4662062B2 (ja) | 2005-06-15 | 2011-03-30 | 信越化学工業株式会社 | レジスト保護膜材料及びパターン形成方法 |
JP4566861B2 (ja) | 2005-08-23 | 2010-10-20 | 富士通株式会社 | レジスト組成物、レジストパターンの形成方法、半導体装置及びその製造方法 |
JP4763511B2 (ja) | 2006-05-26 | 2011-08-31 | 信越化学工業株式会社 | レジスト保護膜材料及びパターン形成方法 |
JP4861237B2 (ja) | 2006-05-26 | 2012-01-25 | 信越化学工業株式会社 | レジスト保護膜材料及びパターン形成方法 |
US7851130B2 (en) * | 2006-09-19 | 2010-12-14 | Fujifilm Corporation | Photosensitive composition, compound for use in the photosensitive composition, and pattern-forming method using the photosensitive composition |
JP5083528B2 (ja) | 2006-09-28 | 2012-11-28 | 信越化学工業株式会社 | 新規光酸発生剤並びにこれを用いたレジスト材料及びパターン形成方法 |
KR101116963B1 (ko) | 2006-10-04 | 2012-03-14 | 신에쓰 가가꾸 고교 가부시끼가이샤 | 고분자 화합물, 레지스트 재료, 및 패턴 형성 방법 |
JP4858714B2 (ja) | 2006-10-04 | 2012-01-18 | 信越化学工業株式会社 | 高分子化合物、レジスト材料、及びパターン形成方法 |
JP4849267B2 (ja) | 2006-10-17 | 2012-01-11 | 信越化学工業株式会社 | レジスト材料及びこれを用いたパターン形成方法 |
JP4554665B2 (ja) | 2006-12-25 | 2010-09-29 | 富士フイルム株式会社 | パターン形成方法、該パターン形成方法に用いられる多重現像用ポジ型レジスト組成物、該パターン形成方法に用いられるネガ現像用現像液及び該パターン形成方法に用いられるネガ現像用リンス液 |
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 |
JP4982288B2 (ja) | 2007-04-13 | 2012-07-25 | 富士フイルム株式会社 | パターン形成方法 |
JP5011018B2 (ja) | 2007-04-13 | 2012-08-29 | 富士フイルム株式会社 | パターン形成方法 |
US8034547B2 (en) | 2007-04-13 | 2011-10-11 | Fujifilm Corporation | Pattern forming method, resist composition to be used in the pattern forming method, negative developing solution to be used in the pattern forming method and rinsing solution for negative development to be used in the pattern forming method |
JP4617337B2 (ja) | 2007-06-12 | 2011-01-26 | 富士フイルム株式会社 | パターン形成方法 |
JP4590431B2 (ja) | 2007-06-12 | 2010-12-01 | 富士フイルム株式会社 | パターン形成方法 |
JP4993138B2 (ja) | 2007-09-26 | 2012-08-08 | 信越化学工業株式会社 | レジスト材料及びこれを用いたパターン形成方法 |
KR101330944B1 (ko) * | 2007-10-15 | 2013-11-18 | 제이에스알 가부시끼가이샤 | 술폰 화합물, 술폰산염 및 감방사선성 수지 조성물 |
JP4961324B2 (ja) | 2007-10-26 | 2012-06-27 | 富士フイルム株式会社 | 電子線、x線又はeuv用ポジ型レジスト組成物及びそれを用いたパターン形成方法 |
JP5131461B2 (ja) | 2008-02-14 | 2013-01-30 | 信越化学工業株式会社 | 高分子化合物、レジスト材料、及びパターン形成方法 |
JP5071658B2 (ja) | 2008-02-14 | 2012-11-14 | 信越化学工業株式会社 | レジスト材料、レジスト保護膜材料、及びパターン形成方法 |
JP5245956B2 (ja) | 2008-03-25 | 2013-07-24 | 信越化学工業株式会社 | 新規光酸発生剤並びにこれを用いたレジスト材料及びパターン形成方法 |
JP4569786B2 (ja) | 2008-05-01 | 2010-10-27 | 信越化学工業株式会社 | 新規光酸発生剤並びにこれを用いたレジスト材料及びパターン形成方法 |
JP4650644B2 (ja) | 2008-05-12 | 2011-03-16 | 信越化学工業株式会社 | レジスト材料及びパターン形成方法 |
JP5201363B2 (ja) | 2008-08-28 | 2013-06-05 | 信越化学工業株式会社 | 重合性アニオンを有するスルホニウム塩及び高分子化合物、レジスト材料及びパターン形成方法 |
TWI400226B (zh) | 2008-10-17 | 2013-07-01 | Shinetsu Chemical Co | 具有聚合性陰離子之鹽及高分子化合物、光阻劑材料及圖案形成方法 |
JP4666190B2 (ja) | 2008-10-30 | 2011-04-06 | 信越化学工業株式会社 | レジスト材料及びパターン形成方法 |
JP4813537B2 (ja) | 2008-11-07 | 2011-11-09 | 信越化学工業株式会社 | 熱酸発生剤を含有するレジスト下層材料、レジスト下層膜形成基板及びパターン形成方法 |
JP4748331B2 (ja) | 2008-12-02 | 2011-08-17 | 信越化学工業株式会社 | レジスト材料及びパターン形成方法 |
JP5368270B2 (ja) | 2009-02-19 | 2013-12-18 | 信越化学工業株式会社 | 新規スルホン酸塩及びその誘導体、光酸発生剤並びにこれを用いたレジスト材料及びパターン形成方法 |
JP5170456B2 (ja) | 2009-04-16 | 2013-03-27 | 信越化学工業株式会社 | レジスト材料及びパターン形成方法 |
US8017198B2 (en) | 2009-04-24 | 2011-09-13 | Ovshinsky Innovation Llc | Thin film deposition via charged particle-depleted plasma achieved by magnetic confinement |
US8791288B2 (en) * | 2009-05-26 | 2014-07-29 | Shin-Etsu Chemical Co., Ltd. | Acid-labile ester monomer having spirocyclic structure, polymer, resist composition, and patterning process |
JP5387181B2 (ja) | 2009-07-08 | 2014-01-15 | 信越化学工業株式会社 | スルホニウム塩、レジスト材料及びパターン形成方法 |
KR101871500B1 (ko) | 2010-07-29 | 2018-06-26 | 스미또모 가가꾸 가부시끼가이샤 | 염 및 포토레지스트 조성물 |
JP5510176B2 (ja) | 2010-08-17 | 2014-06-04 | 信越化学工業株式会社 | レジスト材料及びパターン形成方法 |
JP5246220B2 (ja) | 2010-08-23 | 2013-07-24 | 信越化学工業株式会社 | スルホニウム塩、レジスト材料及びパターン形成方法 |
JP5848869B2 (ja) * | 2010-08-25 | 2016-01-27 | 富士フイルム株式会社 | パターン形成方法 |
JP5767919B2 (ja) * | 2010-09-17 | 2015-08-26 | 富士フイルム株式会社 | パターン形成方法 |
US8597869B2 (en) | 2010-10-25 | 2013-12-03 | Shin-Etsu Chemical Co., Ltd. | Sulfonium salt, resist composition, and patterning process |
JP5561184B2 (ja) | 2011-01-26 | 2014-07-30 | 信越化学工業株式会社 | スルホニウム塩 |
JP5556765B2 (ja) | 2011-08-05 | 2014-07-23 | 信越化学工業株式会社 | ArF液浸露光用化学増幅ポジ型レジスト材料及びパターン形成方法 |
JP5737242B2 (ja) * | 2012-08-10 | 2015-06-17 | 信越化学工業株式会社 | 単量体、高分子化合物、レジスト組成物及びパターン形成方法 |
JP5815575B2 (ja) | 2013-01-11 | 2015-11-17 | 信越化学工業株式会社 | パターン形成方法 |
-
2015
- 2015-04-28 JP JP2015091338A patent/JP6394481B2/ja active Active
-
2016
- 2016-04-07 EP EP16164164.2A patent/EP3088955B1/en active Active
- 2016-04-26 TW TW105112880A patent/TWI614580B/zh active
- 2016-04-27 KR KR1020160051603A patent/KR102071757B1/ko active IP Right Grant
- 2016-04-27 US US15/139,831 patent/US9921479B2/en active Active
- 2016-04-28 CN CN201610272230.2A patent/CN106094450B/zh active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2000250204A (ja) * | 1999-03-04 | 2000-09-14 | Shin Etsu Chem Co Ltd | フォトレジスト材料およびパターン形成方法 |
JP2009515944A (ja) * | 2005-11-16 | 2009-04-16 | エイゼット・エレクトロニック・マテリアルズ・ユーエスエイ・コーポレイション | 光活性化合物 |
JP2010152068A (ja) * | 2008-12-25 | 2010-07-08 | Tokyo Ohka Kogyo Co Ltd | レジスト組成物、およびレジストパターン形成方法 |
WO2012053396A1 (ja) * | 2010-10-19 | 2012-04-26 | Jsr株式会社 | レジストパターン形成方法及び感放射線性樹脂組成物 |
JP2014199389A (ja) * | 2012-07-24 | 2014-10-23 | 富士フイルム株式会社 | 感活性光線性又は感放射線性樹脂組成物、該組成物を用いた感活性光線性又は感放射線性膜及びパターン形成方法、並びに電子デバイスの製造方法及び電子デバイス |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPWO2018116915A1 (ja) * | 2016-12-22 | 2019-11-21 | 富士フイルム株式会社 | 感活性光線性又は感放射線性樹脂組成物、感活性光線性又は感放射線性膜、パターン形成方法、及び、電子デバイスの製造方法 |
CN110192152A (zh) * | 2017-01-13 | 2019-08-30 | 日产化学株式会社 | 包含酰胺溶剂的抗蚀剂下层膜形成用组合物 |
CN110192152B (zh) * | 2017-01-13 | 2023-11-03 | 日产化学株式会社 | 包含酰胺溶剂的抗蚀剂下层膜形成用组合物 |
WO2020044771A1 (ja) * | 2018-08-29 | 2020-03-05 | 富士フイルム株式会社 | 感活性光線性又は感放射線性樹脂組成物、レジスト膜、パターン形成方法、電子デバイスの製造方法 |
JPWO2020044771A1 (ja) * | 2018-08-29 | 2021-09-24 | 富士フイルム株式会社 | 感活性光線性又は感放射線性樹脂組成物、レジスト膜、パターン形成方法、電子デバイスの製造方法 |
JP7333325B2 (ja) | 2018-08-29 | 2023-08-24 | 富士フイルム株式会社 | 感活性光線性又は感放射線性樹脂組成物、レジスト膜、パターン形成方法、電子デバイスの製造方法 |
WO2020209527A1 (ko) * | 2019-04-09 | 2020-10-15 | 영창케미칼 주식회사 | 고두께 스핀 온 카본 하드마스크 조성물 및 이를 이용한 패턴화 방법 |
KR20200119053A (ko) * | 2019-04-09 | 2020-10-19 | 영창케미칼 주식회사 | 고두께 스핀 온 카본 하드마스크 조성물 및 이를 이용한 패턴화 방법 |
KR102240213B1 (ko) | 2019-04-09 | 2021-04-14 | 영창케미칼 주식회사 | 고두께 스핀 온 카본 하드마스크 조성물 및 이를 이용한 패턴화 방법 |
JP2021021773A (ja) * | 2019-07-25 | 2021-02-18 | 東京応化工業株式会社 | レジスト組成物及びレジストパターン形成方法 |
JP7376269B2 (ja) | 2019-07-25 | 2023-11-08 | 東京応化工業株式会社 | レジスト組成物及びレジストパターン形成方法 |
Also Published As
Publication number | Publication date |
---|---|
JP6394481B2 (ja) | 2018-09-26 |
EP3088955B1 (en) | 2020-06-03 |
KR102071757B1 (ko) | 2020-01-30 |
CN106094450A (zh) | 2016-11-09 |
EP3088955A2 (en) | 2016-11-02 |
KR20160128244A (ko) | 2016-11-07 |
US9921479B2 (en) | 2018-03-20 |
US20160320699A1 (en) | 2016-11-03 |
TW201701073A (zh) | 2017-01-01 |
EP3088955A3 (en) | 2017-06-14 |
CN106094450B (zh) | 2020-05-05 |
TWI614580B (zh) | 2018-02-11 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6394481B2 (ja) | レジスト組成物及びパターン形成方法 | |
JP6651965B2 (ja) | 単量体、高分子化合物、レジスト組成物及びパターン形成方法 | |
JP6237428B2 (ja) | パターン形成方法 | |
JP6319188B2 (ja) | スルホニウム塩、化学増幅レジスト組成物、及びパターン形成方法 | |
JP5812030B2 (ja) | スルホニウム塩及び高分子化合物、レジスト材料及びパターン形成方法 | |
JP5783137B2 (ja) | スルホニウム塩、高分子化合物、レジスト材料及びパターン形成方法 | |
JP6520524B2 (ja) | レジスト材料及びパターン形成方法 | |
JP6673105B2 (ja) | スルホニウム化合物、レジスト組成物及びパターン形成方法 | |
JP5815575B2 (ja) | パターン形成方法 | |
JP6658204B2 (ja) | 光酸発生剤、レジスト組成物及びパターン形成方法 | |
KR102117759B1 (ko) | 레지스트 조성물 및 패턴 형성 방법 | |
JP2018062503A (ja) | スルホニウム化合物、レジスト組成物、及びパターン形成方法 | |
JP5815576B2 (ja) | パターン形成方法 | |
JP6332113B2 (ja) | シュリンク材料及びパターン形成方法 | |
JP6398848B2 (ja) | シュリンク材料及びパターン形成方法 | |
JP2021110922A (ja) | ポジ型レジスト材料及びパターン形成方法 | |
KR20190121709A (ko) | 광산 발생제, 화학 증폭 레지스트 재료 및 패턴 형성 방법 | |
TWI836526B (zh) | 正型阻劑材料及圖案形成方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20170425 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20171226 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20171220 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20180214 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20180731 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20180813 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6394481 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |