JP7517106B2 - オニウム塩化合物、化学増幅レジスト組成物及びパターン形成方法 - Google Patents
オニウム塩化合物、化学増幅レジスト組成物及びパターン形成方法 Download PDFInfo
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- JP7517106B2 JP7517106B2 JP2020194996A JP2020194996A JP7517106B2 JP 7517106 B2 JP7517106 B2 JP 7517106B2 JP 2020194996 A JP2020194996 A JP 2020194996A JP 2020194996 A JP2020194996 A JP 2020194996A JP 7517106 B2 JP7517106 B2 JP 7517106B2
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- -1 salt compound Chemical class 0.000 title claims description 262
- 239000000203 mixture Substances 0.000 title claims description 60
- 238000000034 method Methods 0.000 title claims description 37
- 239000002253 acid Substances 0.000 claims description 173
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 148
- 238000009792 diffusion process Methods 0.000 claims description 93
- 125000004432 carbon atom Chemical group C* 0.000 claims description 92
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 84
- 239000003112 inhibitor Substances 0.000 claims description 81
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 45
- 125000000743 hydrocarbylene group Chemical group 0.000 claims description 44
- 229920005601 base polymer Polymers 0.000 claims description 35
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
- 229910052731 fluorine Inorganic materials 0.000 claims description 30
- 125000001153 fluoro group Chemical group F* 0.000 claims description 29
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 27
- 125000005843 halogen group Chemical group 0.000 claims description 27
- 229910052799 carbon Inorganic materials 0.000 claims description 23
- 150000001721 carbon Chemical group 0.000 claims description 22
- 150000001768 cations Chemical class 0.000 claims description 22
- 239000003960 organic solvent Substances 0.000 claims description 22
- 229920000642 polymer Polymers 0.000 claims description 22
- 239000007864 aqueous solution Substances 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 19
- 229910052740 iodine Inorganic materials 0.000 claims description 18
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 13
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 13
- 150000001244 carboxylic acid anhydrides Chemical group 0.000 claims description 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
- 239000000758 substrate Substances 0.000 claims description 12
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 11
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 10
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 claims description 10
- 230000009471 action Effects 0.000 claims description 9
- 150000008053 sultones Chemical group 0.000 claims description 9
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 claims description 6
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical group CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 claims description 6
- IKDIJXDZEYHZSD-UHFFFAOYSA-N 2-phenylethyl formate Chemical compound O=COCCC1=CC=CC=C1 IKDIJXDZEYHZSD-UHFFFAOYSA-N 0.000 claims description 6
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 claims description 6
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-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
- CRZQGDNQQAALAY-UHFFFAOYSA-N Methyl benzeneacetate Chemical compound COC(=O)CC1=CC=CC=C1 CRZQGDNQQAALAY-UHFFFAOYSA-N 0.000 claims description 6
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 claims description 6
- NMJJFJNHVMGPGM-UHFFFAOYSA-N butyl formate Chemical compound CCCCOC=O NMJJFJNHVMGPGM-UHFFFAOYSA-N 0.000 claims description 6
- 238000010894 electron beam technology Methods 0.000 claims description 6
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 claims description 6
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 6
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 claims description 6
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 claims description 6
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 claims description 6
- RPUSRLKKXPQSGP-UHFFFAOYSA-N methyl 3-phenylpropanoate Chemical compound COC(=O)CCC1=CC=CC=C1 RPUSRLKKXPQSGP-UHFFFAOYSA-N 0.000 claims description 6
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 6
- HNBDRPTVWVGKBR-UHFFFAOYSA-N n-pentanoic acid methyl ester Natural products CCCCC(=O)OC HNBDRPTVWVGKBR-UHFFFAOYSA-N 0.000 claims description 6
- VKCYHJWLYTUGCC-UHFFFAOYSA-N nonan-2-one Chemical compound CCCCCCCC(C)=O VKCYHJWLYTUGCC-UHFFFAOYSA-N 0.000 claims description 6
- PGMYKACGEOXYJE-UHFFFAOYSA-N pentyl acetate Chemical compound CCCCCOC(C)=O PGMYKACGEOXYJE-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
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 claims description 6
- 229940116333 ethyl lactate Drugs 0.000 claims description 5
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-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
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-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
- ULPMRIXXHGUZFA-UHFFFAOYSA-N (R)-4-Methyl-3-hexanone Natural products CCC(C)C(=O)CC ULPMRIXXHGUZFA-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- 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 3
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 claims description 3
- AVMSWPWPYJVYKY-UHFFFAOYSA-N 2-Methylpropyl formate Chemical compound CC(C)COC=O AVMSWPWPYJVYKY-UHFFFAOYSA-N 0.000 claims description 3
- QGLVWTFUWVTDEQ-UHFFFAOYSA-N 2-chloro-3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1Cl QGLVWTFUWVTDEQ-UHFFFAOYSA-N 0.000 claims description 3
- WBPAQKQBUKYCJS-UHFFFAOYSA-N 2-methylpropyl 2-hydroxypropanoate Chemical compound CC(C)COC(=O)C(C)O WBPAQKQBUKYCJS-UHFFFAOYSA-N 0.000 claims description 3
- PFCHFHIRKBAQGU-UHFFFAOYSA-N 3-hexanone Chemical compound CCCC(=O)CC PFCHFHIRKBAQGU-UHFFFAOYSA-N 0.000 claims description 3
- CRORGGSWAKIXSA-UHFFFAOYSA-N 3-methylbutyl 2-hydroxypropanoate Chemical compound CC(C)CCOC(=O)C(C)O CRORGGSWAKIXSA-UHFFFAOYSA-N 0.000 claims description 3
- VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- MRABAEUHTLLEML-UHFFFAOYSA-N Butyl lactate Chemical compound CCCCOC(=O)C(C)O MRABAEUHTLLEML-UHFFFAOYSA-N 0.000 claims description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 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
- 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
- NLAMRLZPVVKXTK-SNAWJCMRSA-N [(e)-but-1-enyl] acetate Chemical compound CC\C=C\OC(C)=O NLAMRLZPVVKXTK-SNAWJCMRSA-N 0.000 claims description 3
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 claims description 3
- DULCUDSUACXJJC-UHFFFAOYSA-N benzeneacetic acid ethyl ester Natural products CCOC(=O)CC1=CC=CC=C1 DULCUDSUACXJJC-UHFFFAOYSA-N 0.000 claims description 3
- 229940007550 benzyl acetate Drugs 0.000 claims description 3
- 239000001191 butyl (2R)-2-hydroxypropanoate Substances 0.000 claims description 3
- 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 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
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 claims description 3
- XKYICAQFSCFURC-UHFFFAOYSA-N isoamyl formate Chemical compound CC(C)CCOC=O XKYICAQFSCFURC-UHFFFAOYSA-N 0.000 claims description 3
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 claims description 3
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 claims description 3
- 229940095102 methyl benzoate Drugs 0.000 claims description 3
- 229940057867 methyl lactate Drugs 0.000 claims description 3
- MBAHGFJTIVZLFB-UHFFFAOYSA-N methyl pent-2-enoate Chemical compound CCC=CC(=O)OC MBAHGFJTIVZLFB-UHFFFAOYSA-N 0.000 claims description 3
- 229940017219 methyl propionate Drugs 0.000 claims description 3
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 3
- GXOHBWLPQHTYPF-UHFFFAOYSA-N pentyl 2-hydroxypropanoate Chemical compound CCCCCOC(=O)C(C)O GXOHBWLPQHTYPF-UHFFFAOYSA-N 0.000 claims description 3
- 229940049953 phenylacetate Drugs 0.000 claims description 3
- ILVGAIQLOCKNQA-UHFFFAOYSA-N propyl 2-hydroxypropanoate Chemical compound CCCOC(=O)C(C)O ILVGAIQLOCKNQA-UHFFFAOYSA-N 0.000 claims description 3
- 229940090181 propyl acetate Drugs 0.000 claims description 3
- 125000005650 substituted phenylene group Chemical group 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
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 3
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000000686 lactone group Chemical group 0.000 claims 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 81
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 69
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
- 239000012044 organic layer Substances 0.000 description 55
- 125000005842 heteroatom Chemical group 0.000 description 48
- 230000002829 reductive effect Effects 0.000 description 48
- 150000001450 anions Chemical class 0.000 description 43
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 41
- 239000007787 solid Substances 0.000 description 40
- 230000035945 sensitivity Effects 0.000 description 34
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
- 230000015572 biosynthetic process Effects 0.000 description 32
- 150000003839 salts Chemical class 0.000 description 31
- 238000003786 synthesis reaction Methods 0.000 description 31
- 239000000243 solution Substances 0.000 description 30
- 238000001269 time-of-flight mass spectrometry Methods 0.000 description 28
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 27
- 229910052717 sulfur Inorganic materials 0.000 description 25
- 125000004434 sulfur atom Chemical group 0.000 description 25
- 125000004122 cyclic group Chemical group 0.000 description 24
- 239000004094 surface-active agent Substances 0.000 description 24
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 20
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 18
- 125000004433 nitrogen atom Chemical group N* 0.000 description 18
- 125000004430 oxygen atom Chemical group O* 0.000 description 18
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 18
- 239000007788 liquid Substances 0.000 description 17
- 238000001459 lithography Methods 0.000 description 17
- 229920006395 saturated elastomer Polymers 0.000 description 16
- 150000002596 lactones Chemical group 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 238000005160 1H NMR spectroscopy Methods 0.000 description 14
- 238000005481 NMR spectroscopy Methods 0.000 description 14
- 238000000816 matrix-assisted laser desorption--ionisation Methods 0.000 description 14
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 13
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 13
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000006228 supernatant Substances 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 10
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 150000007942 carboxylates Chemical group 0.000 description 9
- 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 9
- 238000011161 development Methods 0.000 description 9
- 230000018109 developmental process Effects 0.000 description 9
- 230000006870 function Effects 0.000 description 9
- 125000001188 haloalkyl group Chemical group 0.000 description 9
- 238000010791 quenching Methods 0.000 description 9
- 230000007261 regionalization Effects 0.000 description 9
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 8
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 8
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 8
- 235000011114 ammonium hydroxide Nutrition 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
- 150000002148 esters Chemical class 0.000 description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- 238000001228 spectrum Methods 0.000 description 8
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- 238000011156 evaluation Methods 0.000 description 7
- 239000011259 mixed solution Substances 0.000 description 7
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 7
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 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
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 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
- 235000006408 oxalic acid Nutrition 0.000 description 6
- 230000003595 spectral effect Effects 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
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- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
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- 238000001308 synthesis method Methods 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
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- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- VMJFYMAHEGJHFH-UHFFFAOYSA-M triphenylsulfanium;bromide Chemical compound [Br-].C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 VMJFYMAHEGJHFH-UHFFFAOYSA-M 0.000 description 1
- ZFEAYIKULRXTAR-UHFFFAOYSA-M triphenylsulfanium;chloride Chemical compound [Cl-].C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 ZFEAYIKULRXTAR-UHFFFAOYSA-M 0.000 description 1
- NBNZEBUNZGWIRJ-UHFFFAOYSA-N triphenylsulfanium;nitrate Chemical compound [O-][N+]([O-])=O.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 NBNZEBUNZGWIRJ-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
- C07C381/12—Sulfonium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/88—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with esterified carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/58—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/53—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
- C07C233/54—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of a saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/18—Polycyclic aromatic halogenated hydrocarbons
-
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Description
1.下記式(1)で表されるオニウム塩化合物。
Rf1及びRf2は、それぞれ独立に、水素原子、フッ素原子又はトリフルオロメチル基であるが、少なくとも一方は、フッ素原子又はトリフルオロメチル基である。
L1は、単結合又は炭素数1~15のヒドロカルビレン基であり、該ヒドロカルビレン基中の水素原子が、ヘテロ原子を含む基で置換されていてもよく、該ヒドロカルビレン基中の-CH2-が、-O-又は-C(=O)-で置換されていてもよい。
L2は、単結合、エーテル結合又はエステル結合である。
Arは、炭素数3~15の(n+1)価の芳香族基であり、該芳香族基の水素原子の一部又は全部が置換基で置換されていてもよい。
nは、1≦n≦5を満たす整数である。
M+は、スルホニウムカチオン又はヨードニウムカチオンである。)
2.下記式(2)で表される1のオニウム塩化合物。
n及びmは、1≦n≦5、0≦m≦4及び1≦n+m≦5を満たす整数である。
R3は、水素原子又はヘテロ原子を含んでいてもよい炭素数1~10のヒドロカルビル基である。
R4は、フッ素原子、ヒドロキシ基又は炭素数1~15のヒドロカルビル基であり、該ヒドロカルビル基中の水素原子が、ヘテロ原子を含む基で置換されていてもよく、該ヒドロカルビル基中の-CH2-が、-O-、-C(=O)-又は-N(RN)-で置換されていてもよい。RNは、水素原子又は炭素数1~10のヒドロカルビル基であり、該ヒドロカルビル基RN中の水素原子が、ヘテロ原子を含む基で置換されていてもよく、該ヒドロカルビル基RN中の-CH2-が、-O-、-C(=O)-又は-S(=O)2-で置換されていてもよい。mが2以上のとき、各R4は、互いに同一であっても異なっていてもよく、2つのR4が互いに結合してこれらが結合するベンゼン環上の炭素原子と共に環を形成してもよい。
L3は、単結合、エーテル結合又はエステル結合である。
L4は、単結合、又はヘテロ原子を含んでいてもよい炭素数1~10のヒドロカルビレン基である。)
3.R3が、水素原子、イソプロピル基、アダマンチル基又は置換されていてもよいフェニル基である2のオニウム塩化合物。
4.L3及びL4が、単結合である2又は3のオニウム塩化合物。
5.M+が、下記式(M-1)~(M-4)のいずれかで表されるカチオンである1~4のいずれかのオニウム塩化合物。
L5及びL6は、それぞれ独立に、単結合、-CH2-、-O-、-C(=O)-、-S-、-S(=O)-、-S(=O)2-又は-N(RN)-である。
RNは、水素原子又は炭素数1~10のヒドロカルビル基であり、該ヒドロカルビル基中の水素原子が、ヘテロ原子を含む基で置換されていてもよく、該ヒドロカルビル基中の-CH2-が、-O-、-C(=O)-又は-S(=O)2-で置換されていてもよい。
p、q、r、s及びtは、それぞれ独立に、0~5の整数である。pが2以上のとき、各RM1は、互いに同一でも異なっていてもよく、2つのRM1が互いに結合してこれらが結合するベンゼン環上の炭素原子と共に環を形成してもよい。qが2以上のとき、各RM2は、互いに同一でも異なっていてもよく、2つのRM2が互いに結合してこれらが結合するベンゼン環上の炭素原子と共に環を形成してもよい。rが2以上のとき、各RM3は、互いに同一でも異なっていてもよく、2つのRM3が互いに結合してこれらが結合するベンゼン環上の炭素原子と共に環を形成してもよい。sが2以上のとき、各RM4は、互いに同一でも異なっていてもよく、2つのRM4が互いに結合してこれらが結合するベンゼン環上の炭素原子と共に環を形成してもよい。tが2以上のとき、各RM5は、互いに同一でも異なっていてもよく、2つのRM5が互いに結合してこれらが結合するベンゼン環上の炭素原子と共に環を形成してもよい。)
6.下記式(3)又は(4)で表される5のオニウム塩化合物。
R5は、フッ素原子、ヒドロキシ基又は炭素数1~10のヒドロカルビル基であり、該ヒドロカルビル基中の水素原子が、ヘテロ原子を含む基で置換されていてもよく、該ヒドロカルビル基中の-CH2-が、-O-又は-C(=O)-で置換されていてもよい。mが2以上のとき、各R5は、互いに同一であっても異なっていてもよく、2つのR5が互いに結合してこれらが結合する炭素原子と共に環を形成してもよい。)
7.nが、2又は3である6のオニウム塩化合物。
8.1~7のいずれかのオニウム塩化合物からなる酸拡散抑制剤。
9.(A)酸の作用により現像液に対する溶解性が変化するベースポリマー、(B)光酸発生剤、(C)1~7のいずれかのオニウム塩化合物を含む酸拡散抑制剤、及び(D)有機溶剤を含む化学増幅レジスト組成物。
10.(A')酸の作用により現像液に対する溶解性が変化し、露光により酸を発生する機能を有する繰り返し単位を含むベースポリマー、(C)1~7のいずれかのオニウム塩化合物を含む酸拡散抑制剤、及び(D)有機溶剤を含む化学増幅レジスト組成物。
11.前記ベースポリマーが、下記式(a)で表される繰り返し単位又は下記式(b)で表される繰り返し単位を含むポリマーである9又は10の化学増幅レジスト組成物。
XAは、単結合、フェニレン基、ナフチレン基又は(主鎖)-C(=O)-O-XA1-である。XA1は、ヒドロキシ基、エーテル結合、エステル結合又はラクトン環を含んでいてもよい炭素数1~15のヒドロカルビレン基である。
XBは、単結合又はエステル結合である。
AL1及びAL2は、それぞれ独立に、酸不安定基である。)
12.前記酸不安定基が、下記式(L1)で表される基である11の化学増幅レジスト組成物。
13.前記ベースポリマーが、下記式(c)で表される繰り返し単位を含むポリマーである9~12のいずれかの化学増幅レジスト組成物。
YAは、単結合又はエステル結合である。
R21は、フッ素原子、ヨウ素原子又は炭素数1~10のヒドロカルビル基であり、該ヒドロカルビル基中の-CH2-が、-O-又は-C(=O)-で置換されていてもよい。
b及びcは、1≦b≦5、0≦c≦4及び1≦b+c≦5を満たす整数である。)
14.露光により酸を発生する機能を有する繰り返し単位が、下記式(d1)~(d4)で表されるものから選ばれる少なくとも1種である10の化学増幅レジスト組成物。
ZAは、単結合、フェニレン基、-O-ZA1-、-C(=O)-O-ZA1-又は-C(=O)-NH-ZA1-である。ZA1は、ヘテロ原子を含んでいてもよい炭素数1~20のヒドロカルビレン基である。
ZB及びZCは、それぞれ独立に、単結合、又はヘテロ原子を含んでいてもよい炭素数1~20のヒドロカルビレン基である。
ZDは、単結合、メチレン基、エチレン基、フェニレン基、フッ素化されたフェニレン基、-O-ZD1-、-C(=O)-O-ZD1又は-C(=O)-NH-ZD1-である。ZD1は、置換されていてもよいフェニレン基である。
R31~R41は、それぞれ独立に、ヘテロ原子を含んでいてもよい炭素数1~20のヒドロカルビル基である。また、ZA、R31及びR32のうちのいずれか2つが、互いに結合してこれらが結合する硫黄原子と共に環を形成してもよく、R33、R34及びR35のうちのいずれか2つ、R36、R37及びR38のうちのいずれか2つ又はR39、R40及びR41のうちのいずれか2つが、互いに結合してこれらが結合する硫黄原子と共に環を形成してもよい。
RHFは、水素原子又はトリフルオロメチル基である。
n1は、0又は1であるが、ZBが単結合のときは0である。n2は、0又は1であるが、ZCが単結合のときは0である。
Xa-は、非求核性対向イオンである。)
15.9~14のいずれかの化学増幅レジスト組成物を用いて、基板上にレジスト膜を形成する工程と、前記レジスト膜をKrFエキシマレーザー光、ArFエキシマレーザー光、EB又はEUVで露光する工程と、前記露光したレジスト膜を、現像液を用いて現像する工程とを含むパターン形成方法。
16.現像液としてアルカリ水溶液を用いて、露光部を溶解させ、未露光部が溶解しないポジ型パターンを得る15のパターン形成方法。
17.現像液として有機溶剤を用いて、未露光部を溶解させ、露光部が溶解しないネガ型パターンを得る15のパターン形成方法。
18.前記現像液が、2-オクタノン、2-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、メチルシクロヘキサノン、アセトフェノン、メチルアセトフェノン、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、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、酢酸フェニル、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及び酢酸2-フェニルエチルから選ばれる少なくとも1種である17のパターン形成方法。
本発明の化学増幅レジスト組成物は、
(A)酸の作用により現像液に対する溶解性が変化するベースポリマー、
(B)光酸発生剤、
(C-1)本発明のオニウム塩化合物からなる酸拡散抑制剤、及び
(D)有機溶剤
を必須成分として含み、必要に応じて、
(C-2)本発明のオニウム塩化合物以外の酸拡散抑制剤、
(E)界面活性剤、及び
(F)その他の成分
を含んでもよい。
(C-1)本発明のオニウム塩化合物からなる酸拡散抑制剤、及び
(D)有機溶剤
を必須成分として含み、必要に応じて、
(B)光酸発生剤、
(C-2)本発明のオニウム塩化合物以外の酸拡散抑制剤、
(E)界面活性剤、及び
(F)その他の成分
を含んでもよい。
(A)成分のベースポリマーとしては、下記式(a)で表される繰り返し単位(以下、繰り返し単位aともいう。)又は下記式(b)で表される繰り返し単位(以下、繰り返し単位bともいう。)を含むポリマーが好ましい。
(I)繰り返し単位a及びbから選ばれる1種又は2種以上を好ましくは10~70モル%、より好ましくは20~65モル%、更に好ましくは30~60モル%含み、必要に応じ、
(II)繰り返し単位cの1種又は2種以上を好ましくは0~90モル%、より好ましくは15~80モル%、更に好ましくは30~60モル%含み、必要に応じ、
(III)繰り返し単位d1~d4から選ばれる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0~15モル%含み、必要に応じ、
(IV)繰り返し単位e及び他の繰り返し単位から選ばれる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%含むことができる。
本発明のレジスト組成物は、前記ベースポリマーが繰り返し単位d1~d4から選ばれる少なくとも1つを含まない場合、必須成分として(B)光酸発生剤(以下、添加型光酸発生剤ともいう。)を含む。なお、前記ベースポリマーが繰り返し単位d1~d4から選ばれる少なくとも1つを含む場合であっても、添加型光酸発生剤は含まれていてもよい。
本発明のレジスト組成物は、(C)成分として酸拡散抑制剤を含む。(C)成分は、式(1)で表されるオニウム塩化合物を必須成分(C-1)として含むが、式(1)で表されるオニウム塩化合物以外の酸拡散抑制剤(C-2)を含んでもよい。なお、本発明において酸拡散抑制剤とは、光酸発生剤より発生する酸がレジスト膜中に拡散する際の拡散速度を抑制することができる化合物を意味する。
本発明の化学増幅レジスト組成物は、(D)成分として有機溶剤を含んでもよい。前記有機溶剤としては、前述した各成分や後述する各成分が溶解可能な有機溶剤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、ジアセトンアルコ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tert-ブチル、プロピオン酸tert-ブチル、プロピレングリコールモノtert-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、前記成分以外に、(E)成分として、塗布性を向上させるために慣用されている界面活性剤を含んでもよい。
-C(=O)-O-Rs5A
(式中、Rs5Aは、炭素数1~20のフッ素化ヒドロカルビル基である。)
で表される基である。Rs6は、炭素数1~15のヒドロカルビル基又は炭素数1~15のフッ素化ヒドロカルビル基であり、炭素-炭素結合間に、-O-又は-C(=O)-が介在していてもよい。
本発明の化学増幅レジスト組成物は、(F)その他成分として、酸により分解して酸を発生する化合物(酸増殖化合物)、有機酸誘導体、フッ素置換アルコール、架橋剤、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)、アセチレンアルコール類等を含んでいてもよい。具体的には、前記酸増殖化合物に関しては、特開2009-269953号公報、特開2010-215608号公報に詳しく、その含有量は、(A)ベースポリマー100質量部に対し、0~5質量部が好ましく、0~3質量部がより好ましい。含有量が多すぎると、酸拡散制御が難しく、解像性の劣化やパターン形状の劣化を招く可能性がある。その他の添加剤に関しては、特開2008-122932号公報の段落[0155]~[0182]、特開2009-269953号公報、特開2010-215608号公報に詳しい。
本発明のパターン形成方法は、前述したレジスト組成物を用いて、基板上にレジスト膜を形成する工程、前記レジスト膜を、高エネルギー線で露光する工程、及び前記露光したレジスト膜を、現像液を用いて現像する工程を含む。
得られた2,3,5-トリヨード安息香酸クロリド343g、化合物SM-1 100g及び塩化メチレン1,500gを混合した後、氷冷下、トリエチルアミン77g、N,N-ジメチルアミノピリジン9.3g及び塩化メチレン100gの混合溶液を滴下した。室温で終夜攪拌した後、トリエチルアミン10gを加え、更に2,3,5-トリヨード安息香酸クロリド43g及び塩化メチレン250gの混合溶液を滴下し、室温で終夜攪拌した。2.5質量%塩酸1,500gを加えて30分間攪拌し、反応をクエンチした。析出した固体を濾別し、有機層を回収した。得られた有機層を純水1,200gで3回洗浄した後、活性炭17gを加えて1時間攪拌した。活性炭を濾別した後、飽和炭酸水素ナトリウム水溶液1,200gで1回、及び純水1,200gで3回洗浄した。その後、有機層を減圧濃縮することで、目的の化合物SM-2を赤色の油状物として得た(収量360g)。
19F-NMR (500MHz, DMSO-d6): δ= -113.1 (1F, dd), -109.9 (1F, dd) ppm
IR (D-ATR): ν= 3059, 2968, 1737, 1652, 1520, 1476, 1447, 1381, 1269, 1232, 1184, 1102, 1034, 997, 939, 821, 796, 749, 700, 684, 502 cm-1
飛行時間型質量分析(TOFMS; MALDI)
POSITIVE M+263.1 (C18H15S+相当)
NEGATIVE M-648.8 (C13H10F2I3O4 -相当)
19F-NMR (500MHz, DMSO-d6): δ= -113.1 (1F, dd), -109.9 (1F, dd), -104.6 (1F, m) ppm
IR (D-ATR): ν= 3058, 2969, 1737, 1652, 1587, 1521, 1492, 1476, 1446, 1392, 1269, 1235, 1184, 1102, 1034, 997, 939, 843, 821, 796, 748, 696, 683, 525, 504 cm-1
飛行時間型質量分析(TOFMS; MALDI)
POSITIVE M+281.1 (C18H14FS+相当)
NEGATIVE M-648.8 (C13H10F2I3O4 -相当)
19F-NMR (500MHz, DMSO-d6): δ= -113.1 (1F, dd), -109.9 (1F, dd) ppm
IR (D-ATR): ν= 3061, 2966, 1736, 1647, 1520, 1475, 1448, 1429, 1383, 1268, 1233, 1184, 1102, 1034, 997, 940, 895, 872, 821, 796, 758, 706, 680, 526, 489 cm-1
飛行時間型質量分析(TOFMS; MALDI)
POSITIVE M+261.1 (C18H13S+相当)
NEGATIVE M-648.8 (C13H10F2I3O4 -相当)
19F-NMR (500MHz, DMSO-d6): δ= -115.7 (1F, dd), -110.7 (1F, dd) -104.6 (1F, m) ppm
IR (D-ATR): ν= 3271, 3054, 1641, 1589, 1493, 1477, 1447, 1392, 1321, 1268, 1246, 1178, 1161, 1112, 1094, 1063, 1000, 847, 818, 779, 741, 701, 681, 630, 526, 504, 493, 459 cm-1
飛行時間型質量分析(TOFMS; MALDI)
POSITIVE M+281.1 (C18H14FS+相当)
NEGATIVE M-468.8 (C9H5F2I2O4 -相当)
19F-NMR (500MHz, DMSO-d6): δ= -122.1 (1F, m), -115.7 (1F, dd), -110.7 (1F, dd) ppm
飛行時間型質量分析(TOFMS; MALDI)
POSITIVE M+379.2 (C24H24FOS+相当)
NEGATIVE M-468.8 (C9H5F2I2O4 -相当)
19F-NMR (500MHz, DMSO-d6): δ= -127.7 (1F, m), -113.2 (1F, dd), -110.3 (1F, dd) ppm
IR (D-ATR): ν= 3062, 2969, 1734, 1644, 1603, 1576, 1519, 1475, 1446, 1393, 1367, 1268, 1233, 1210, 1183, 1120, 1103, 1042, 998, 940, 897, 871, 821, 796, 747, 698, 683, 600, 508, 495 cm-1
飛行時間型質量分析(TOFMS; MALDI)
POSITIVE M+297.1 (C18H14FOS+相当)
NEGATIVE M-648.8 (C13H10F2I3O4 -相当)
19F-NMR (500MHz, DMSO-d6): δ= -113.1 (1F, dd), -109.9 (1F, dd), -57.9 (3F, s) ppm
飛行時間型質量分析(TOFMS; MALDI)
POSITIVE M+347.1 (C19H14F3OS+相当)
NEGATIVE M-648.8 (C13H10F2I3O4 -相当)
得られた4-ヨード安息香酸クロリド118.0g、化合物SM-1 78.5g及び塩化メチレン520gを混合した後、氷冷下、トリエチルアミン56.7g、N,N-ジメチルアミノピリジン4.9g及び塩化メチレン80gの混合溶液を滴下した。室温で終夜攪拌した後、氷冷下、飽和炭酸水素ナトリウム水溶液100mL及び純水100mLを加えて反応をクエンチした。有機層を分取し、4質量%塩酸200gで1回、純水200gで1回、飽和炭酸水素ナトリウム水溶液200mLで1回、及び純水200gで2回洗浄した。得られた有機層に活性炭素12.2gを加えて終夜攪拌した後、活性炭を濾別し、濾液を減圧濃縮することで、目的の化合物SM-10を油状物として得た(収量151.4g、収率84.6%)。
19F-NMR (500MHz, DMSO-d6): δ= -115.2 (1F, dd), -107.7 (1F, dd) ppm
飛行時間型質量分析(TOFMS; MALDI)
POSITIVE M+263.1 (C18H15S+相当)
NEGATIVE M-397.0 (C13H12F2IO4 -相当)
19F-NMR (500MHz, DMSO-d6): δ= -113.1 (1F, dd), -109.9 (1F, dd), -104.7 (3F, m) ppm
IR (D-ATR): ν= 3399, 3098, 3053, 2969, 2880, 1737, 1709, 1652, 1586, 1521, 1491, 1394, 1364, 1268, 1240, 1185, 1161, 1102, 1035, 1006, 939, 839, 797, 747, 701, 519 cm-1
飛行時間型質量分析(TOFMS; MALDI)
POSITIVE M+317.1 (C18H12F3S+相当)
NEGATIVE M-648.8 (C13H10F2I3O4 -相当)
19F-NMR (500MHz, DMSO-d6): δ= -113.1 (1F, dd), -109.9 (1F, dd) ppm
飛行時間型質量分析(TOFMS; MALDI)
POSITIVE M+319.2 (C22H23S+相当)
NEGATIVE M-648.8 (C13H10F2I3O4 -相当)
19F-NMR (500MHz, DMSO-d6): δ= -115.2 (1F, dd), -107.8 (1F, d), -104.6 (1F, m) ppm
飛行時間型質量分析(TOFMS; MALDI)
POSITIVE M+281.1 (C18H14FS+相当)
NEGATIVE M-397.0 (C13H12F2IO4 -相当)
19F-NMR (500MHz, DMSO-d6): δ= -115.2 (1F, dd), -107.6 (1F, dd), -57.9 (3F, s) ppm
IR (D-ATR): ν= 3402, 3061, 2969, 1724, 1652, 1587, 1479, 1447, 1393, 1263, 1213, 1178, 1113, 1102, 1038, 1009, 926, 882, 846, 795, 753, 683, 529, 502 cm-1
飛行時間型質量分析(TOFMS; MALDI)
POSITIVE M+347.1 (C19H14F3S+相当)
NEGATIVE M-397.0 (C13H12F2IO4 -相当)
19F-NMR (500MHz, DMSO-d6): δ= -115.1 (1F, dd), -108.2 (1F, d), -105.5 (1F, m) ppm
IR (D-ATR): ν= 3413, 3100, 3061, 2971, 2880, 2797, 2681, 2595, 1723, 1645, 1587, 1492, 1393, 1301, 1266, 1241, 1177, 1162, 1102, 1073, 1042, 1009, 943, 882, 838, 794, 753, 682, 658, 626, 519, 433 cm-1
飛行時間型質量分析(TOFMS; MALDI)
POSITIVE M+315.1 (C18H13F2OS+相当)
NEGATIVE M-397.0 (C13H12F2IO4 -相当)
19F-NMR (500MHz, DMSO-d6): δ= -113.1 (1F, dd), -110.3 (1F, dd), -105.4 (1F, m) ppm
IR (D-ATR): ν= 3398, 3099, 3062, 2970, 2880, 2798, 2681, 2597, 1738, 1645, 1587, 1574, 1522, 1491, 1396, 1300, 1267, 1238, 1183, 1161, 1102, 1072, 1042, 1005, 941, 896, 872, 835, 797, 771, 745, 701, 519, 433 cm-1
飛行時間型質量分析(TOFMS; MALDI)
POSITIVE M+315.1 (C18H13F2OS+相当)
NEGATIVE M-648.8 (C13H10F2I3O4 -相当)
窒素雰囲気下、メタクリル酸1-tert-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。得られた重合液を激しく攪拌したメタノール640g中に滴下し、析出した固体を濾別した。前記固体をメタノール240gで2回洗浄した後、50℃で20時間真空乾燥することで、白色粉末状のポリマーP-1を得た(収量36g、収率90%)。GPCにて分析したところ、ポリマーP-1のMwは8,500、Mw/Mnは1.63であった。
下記表1~4に示す各成分を、界面活性剤Polyfox636(オムノバ社製)0.01質量%を含む溶剤中に溶解させ、得られた溶液を0.2μmのテフロン(登録商標)製フィルターで濾過することで、化学増幅レジスト組成物を調製した。
GBL(γ-ブチロラクトン)
CyHO(シクロヘキサノン)
DAA(ジアセトンアルコール)
Mw=7,700
Mw/Mn=1.82
シリコン基板上に反射防止膜溶液(日産化学(株)製ARC-29A)を塗布し、180℃で60秒間ベークして反射防止膜(膜厚100nm)を形成した。各レジスト組成物(R-1~R-7、R-66~R-68、CR-1~CR-8)を前記反射防止膜上にスピンコーティングし、ホットプレートを用いて100℃で60秒間ベークし、膜厚90nmのレジスト膜を形成した。ArFエキシマレーザースキャナー((株)ニコン製NSR-S610C、NA=1.30、σ0.94/0.74、Dipole-35deg照明、6%ハーフトーン位相シフトマスク)を用いて液浸露光を行った。なお、液浸液としては水を用いた。その後、85℃で60秒間ベーク(PEB)を施し、2.38質量%TMAH水溶液で60秒間現像を行い、ラインアンドスペース(LS)パターンを形成した。
感度として、ライン幅40nm、ピッチ80nmのLSパターンが得られる最適露光量Eop(mJ/cm2)を求めた。この値が小さいほど感度が高い。
Eopで照射して得たLSパターンを、ラインの長手方向に10箇所の寸法を測定し、その結果から標準偏差(σ)の3倍値(3σ)をLWRとして求めた。この値が小さいほど、ラフネスが小さく均一なライン幅のパターンが得られる。
本評価においては、良(〇):2.5nm以下、不良(×):2.5nmより大きい、とした。
各レジスト組成物(R-8~R-65、CR-9~CR-26)を、信越化学工業(株)製ケイ素含有スピンオンハードマスクSHB-A940(ケイ素の含有量が43質量%)を膜厚20nmで形成したシリコン基板上にスピンコートし、ホットプレートを用いて105℃で60秒間プリベークして膜厚50nmのレジスト膜を作製した。これを、ASML社製EUVスキャナーNXE3300(NA0.33、σ0.9/0.6、クアドルポール照明、ウエハー上寸法がピッチ46nm、+20%バイアスのホールパターンのマスク)を用いて露光し、ホットプレート上で90℃で60秒間PEBを行い、2.38質量%TMAH水溶液で30秒間現像を行い、寸法23nmのホールパターンを形成した。
感度として、ホール寸法が23nmで形成されるときの最適露光量Eop(mJ/cm2)を求めた。この値が小さいほど感度が高い。
Eopで照射して得たホールパターンを、同一露光量ショット内50箇所の寸法を測定し、その結果から標準偏差(σ)の3倍値(3σ)をCDUとして求めた。この値が小さいほど、ホールパターンの寸法均一性が優れる。
本評価においては、良(〇):3.0nm以下、不良(×):3.0nmより大きい、とした。
Claims (16)
- 下記式(1)で表されるオニウム塩化合物。
Rf1及びRf2は、それぞれ独立に、水素原子、フッ素原子又はトリフルオロメチル基であるが、少なくとも一方は、フッ素原子又はトリフルオロメチル基である。
L1は、単結合又は炭素数1~15のヒドロカルビレン基であり、該ヒドロカルビレン基中の水素原子が、ハロゲン原子、ヒドロキシ基又はシアノ基で置換されていてもよく、該ヒドロカルビレン基中の-CH2-が、-O-又は-C(=O)-で置換されていてもよい。
L2は、単結合、エーテル結合又はエステル結合である。
Arは、炭素数3~15の(n+1)価の芳香族基であり、該芳香族基の水素原子の一部又は全部が置換基(ただし、下記式(R-1)、(R-2)、(R-3)、(R-4)又及び(R-5)で表される基を除く。)で置換されていてもよい。
nは、1≦n≦5を満たす整数である。
M+は、スルホニウムカチオン又はヨードニウムカチオンである。)
Rr5及びRr6は、それぞれ独立に、水素原子又は炭素数1~5のヒドロカルビル基である。また、Rr4、Rr5及びRr6のいずれか2つが、互いに結合してこれらが結合する原子と共に環を形成してもよい。
破線は、式(1)中のArとの結合手である。) - 下記式(2)で表される請求項1記載のオニウム塩化合物。
n及びmは、1≦n≦5、0≦m≦4及び1≦n+m≦5を満たす整数である。
R3は、水素原子又は炭素数1~10のヒドロカルビル基であり、該ヒドロカルビル基中の水素原子の一部又は全部が、ハロゲン原子、ヒドロキシ基又はシアノ基で置換されていてもよく、該ヒドロカルビル基中の炭素-炭素結合間に、カルボニル基、エーテル結合、エステル結合、スルホン酸エステル結合、カーボネート結合、ラクトン環、スルトン環又はカルボン酸無水物基が介在していてもよい。
R4は、フッ素原子、ヒドロキシ基又は炭素数1~15のヒドロカルビル基であり、該ヒドロカルビル基中の水素原子が、ハロゲン原子、ヒドロキシ基又はシアノ基で置換されていてもよく、該ヒドロカルビル基中の-CH2-が、-O-、-C(=O)-又は-N(RN)-で置換されていてもよい。RNは、水素原子又は炭素数1~10のヒドロカルビル基である。mが2以上のとき、各R4は、互いに同一であっても異なっていてもよい。
L3は、単結合、エーテル結合又はエステル結合である。
L4は、単結合、又は炭素数1~10のヒドロカルビレン基であり、該ヒドロカルビレン基中の水素原子の一部又は全部が、ハロゲン原子、ヒドロキシ基又はシアノ基で置換されていてもよく、該ヒドロカルビレン基中の炭素-炭素結合間に、カルボニル基、エーテル結合、エステル結合、スルホン酸エステル結合、カーボネート結合、ラクトン環、スルトン環又はカルボン酸無水物基が介在していてもよい。) - R3が、水素原子、イソプロピル基、アダマンチル基又は置換されていてもよいフェニル基である請求項2記載のオニウム塩化合物。
- L3及びL4が、単結合である請求項2又は3記載のオニウム塩化合物。
- M+が、下記式(M-1)~(M-4)のいずれかで表されるカチオンである請求項1~4のいずれか1項記載のオニウム塩化合物。
L5及びL6は、それぞれ独立に、単結合、-CH2-、-O-、-C(=O)-、-S-、-S(=O)-、-S(=O)2-又は-N(RN)-である。
RNは、水素原子又は炭素数1~10のヒドロカルビル基である。
p、q、r、s及びtは、それぞれ独立に、0~5の整数である。pが2以上のとき、各RM1は、互いに同一でも異なっていてもよい。qが2以上のとき、各RM2は、互いに同一でも異なっていてもよい。rが2以上のとき、各RM3は、互いに同一でも異なっていてもよい。sが2以上のとき、各RM4は、互いに同一でも異なっていてもよい。tが2以上のとき、各RM5は、互いに同一でも異なっていてもよい。) - 下記式(3)又は(4)で表される請求項5記載のオニウム塩化合物。
L5は、それぞれ独立に、単結合、-CH2-、-O-、-C(=O)-、-S-、-S(=O)-、-S(=O)2-又は-N(RN)-である。
RNは、水素原子又は炭素数1~10のヒドロカルビル基である。
m及びnは、1≦n≦5、0≦m≦4及び1≦n+m≦5を満たす整数である。
p、q及びrは、それぞれ独立に、0~5の整数である。pが2以上のとき、各RM1は、互いに同一でも異なっていてもよい。qが2以上のとき、各RM2は、互いに同一でも異なっていてもよい。rが2以上のとき、各RM3は、互いに同一でも異なっていてもよい。
R5は、フッ素原子、ヒドロキシ基又は炭素数1~10のヒドロカルビル基であり、該ヒドロカルビル基中の水素原子が、ハロゲン原子、ヒドロキシ基又はシアノ基で置換されていてもよく、該ヒドロカルビル基中の-CH2-が、-O-又は-C(=O)-で置換されていてもよい。mが2以上のとき、各R5は、互いに同一であっても異なっていてもよい。) - nが、2又は3である請求項6記載のオニウム塩化合物。
- 請求項1~7のいずれか1項記載のオニウム塩化合物からなる酸拡散抑制剤。
- (A)酸の作用により現像液に対する溶解性が変化するベースポリマー、(B)光酸発生剤、(C)請求項1~7のいずれか1項記載のオニウム塩化合物を含む酸拡散抑制剤、及び(D)有機溶剤を含む化学増幅レジスト組成物であって、
前記ベースポリマーが、下記式(a)で表される繰り返し単位又は下記式(b)で表される繰り返し単位を含むポリマーである化学増幅レジスト組成物。
式(a)で表される繰り返し単位は、下記式のいずれかで表されるものである。
AL1及びAL2は、それぞれ独立に、下記式(L1)で表される基である酸不安定基である。
- (A')酸の作用により現像液に対する溶解性が変化し、露光により酸を発生する機能を有する繰り返し単位を含むベースポリマー、(C)請求項1~7のいずれか1項記載のオニウム塩化合物を含む酸拡散抑制剤、及び(D)有機溶剤を含む化学増幅レジスト組成物であって、
前記露光により酸を発生する機能を有する繰り返し単位が、下記式(d2)~(d4)で表されるものから選ばれる少なくとも1種である化学増幅レジスト組成物。
ZB及びZCは、それぞれ独立に、単結合、又は炭素数1~20のヒドロカルビレン基であり、該ヒドロカルビレン基中の水素原子の一部又は全部が、ハロゲン原子、ヒドロキシ基又はシアノ基で置換されていてもよく、該ヒドロカルビレン基中の炭素-炭素結合間に、カルボニル基、エーテル結合、エステル結合、スルホン酸エステル結合、カーボネート結合、ラクトン環、スルトン環又はカルボン酸無水物基が介在していてもよい。
ZDは、単結合、メチレン基、エチレン基、フェニレン基、フッ素化されたフェニレン基、-O-ZD1-、-C(=O)-O-ZD1又は-C(=O)-NH-ZD1-である。ZD1は、置換されていてもよいフェニレン基である。
RHFは、水素原子又はトリフルオロメチル基である。
n1は、0又は1であるが、ZBが単結合のときは0である。n2は、0又は1であるが、ZCが単結合のときは0である。
式(d2)~(d4)で表される繰り返し単位中のスルホニウムカチオンは、下記式のいずれかで表されるものである。
- 請求項9~12のいずれか1項記載の化学増幅レジスト組成物を用いて、基板上にレジスト膜を形成する工程と、前記レジスト膜をKrFエキシマレーザー光、ArFエキシマレーザー光、電子線又は極端紫外線で露光する工程と、前記露光したレジスト膜を、現像液を用いて現像する工程とを含むパターン形成方法。
- 現像液としてアルカリ水溶液を用いて、露光部を溶解させ、未露光部が溶解しないポジ型パターンを得る請求項13記載のパターン形成方法。
- 現像液として有機溶剤を用いて、未露光部を溶解させ、露光部が溶解しないネガ型パターンを得る請求項13記載のパターン形成方法。
- 前記現像液が、2-オクタノン、2-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、メチルシクロヘキサノン、アセトフェノン、メチルアセトフェノン、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、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、酢酸フェニル、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及び酢酸2-フェニルエチルから選ばれる少なくとも1種である請求項15記載のパターン形成方法。
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