JP2020083760A - 新規塩化合物、化学増幅レジスト組成物、及びパターン形成方法 - Google Patents
新規塩化合物、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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- JP2020083760A JP2020083760A JP2018214718A JP2018214718A JP2020083760A JP 2020083760 A JP2020083760 A JP 2020083760A JP 2018214718 A JP2018214718 A JP 2018214718A JP 2018214718 A JP2018214718 A JP 2018214718A JP 2020083760 A JP2020083760 A JP 2020083760A
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- -1 salt compound Chemical class 0.000 title claims abstract description 231
- 239000000203 mixture Substances 0.000 title claims abstract description 76
- 238000000034 method Methods 0.000 title claims abstract description 59
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- 238000000059 patterning Methods 0.000 title abstract description 7
- 238000010894 electron beam technology Methods 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 114
- 239000002253 acid Substances 0.000 claims description 101
- 125000005842 heteroatom Chemical group 0.000 claims description 76
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 67
- 125000001153 fluoro group Chemical group F* 0.000 claims description 42
- 229910052731 fluorine Inorganic materials 0.000 claims description 40
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 33
- 229920000642 polymer Polymers 0.000 claims description 32
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 31
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- 229910052717 sulfur Inorganic materials 0.000 claims description 27
- 125000004434 sulfur atom Chemical group 0.000 claims description 27
- 150000001450 anions Chemical class 0.000 claims description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
- 239000000243 solution Substances 0.000 claims description 25
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 229920005989 resin Polymers 0.000 claims description 18
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- 150000001875 compounds Chemical class 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 239000007788 liquid Substances 0.000 claims description 14
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- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 claims description 10
- 125000004957 naphthylene group Chemical group 0.000 claims description 10
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- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 9
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 claims description 8
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical group CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 claims description 8
- IKDIJXDZEYHZSD-UHFFFAOYSA-N 2-phenylethyl formate Chemical compound O=COCCC1=CC=CC=C1 IKDIJXDZEYHZSD-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
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 8
- UYWQUFXKFGHYNT-UHFFFAOYSA-N Benzylformate Chemical compound O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 8
- CRZQGDNQQAALAY-UHFFFAOYSA-N Methyl benzeneacetate Chemical compound COC(=O)CC1=CC=CC=C1 CRZQGDNQQAALAY-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
- 125000003178 carboxy group Chemical group [H]OC(*)=O 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
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-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
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-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
- RPUSRLKKXPQSGP-UHFFFAOYSA-N methyl 3-phenylpropanoate Chemical compound COC(=O)CCC1=CC=CC=C1 RPUSRLKKXPQSGP-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
- VKCYHJWLYTUGCC-UHFFFAOYSA-N nonan-2-one Chemical compound CCCCCCCC(C)=O VKCYHJWLYTUGCC-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
- MDHYEMXUFSJLGV-UHFFFAOYSA-N phenethyl acetate Chemical compound CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 claims description 8
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 8
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 7
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 7
- 150000002892 organic cations Chemical class 0.000 claims description 7
- 230000007261 regionalization Effects 0.000 claims description 7
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 6
- 229940116333 ethyl lactate Drugs 0.000 claims description 5
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 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
- 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
- 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
- VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-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
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims description 4
- ZFDIRQKJPRINOQ-HWKANZROSA-N Ethyl crotonate Chemical compound CCOC(=O)\C=C\C ZFDIRQKJPRINOQ-HWKANZROSA-N 0.000 claims description 4
- XYVQFUJDGOBPQI-UHFFFAOYSA-N Methyl-2-hydoxyisobutyric acid Chemical compound COC(=O)C(C)(C)O XYVQFUJDGOBPQI-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
- 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
- GFUIDHWFLMPAGY-UHFFFAOYSA-N ethyl 2-hydroxy-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)O GFUIDHWFLMPAGY-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
- 125000003709 fluoroalkyl group Chemical group 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
- 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
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- 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-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims description 4
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- ZFDIRQKJPRINOQ-UHFFFAOYSA-N transbutenic acid ethyl ester Natural products CCOC(=O)C=CC ZFDIRQKJPRINOQ-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
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- 125000001183 hydrocarbyl group Chemical group 0.000 claims 13
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- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 8
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- 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 7
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- 238000002329 infrared spectrum Methods 0.000 description 4
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
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- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- DOMTZTVJNZKUNX-UHFFFAOYSA-N tert-butyl 3-aminopropanoate;hydrochloride Chemical compound Cl.CC(C)(C)OC(=O)CCN DOMTZTVJNZKUNX-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
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- C07C309/01—Sulfonic acids
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- C07C309/12—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton containing esterified hydroxy groups bound to the carbon skeleton
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- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
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- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
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- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/08—Hydrogen atoms or radicals containing only hydrogen and carbon atoms
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- C07D—HETEROCYCLIC COMPOUNDS
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- C07D333/76—Dibenzothiophenes
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- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
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Abstract
Description
1.下記式(A)で表される塩化合物。
2.m及びnが1であり、Rf1及びRf2がフッ素原子であり、Rf3及びRf4が水素原子である1の塩化合物。
3.m及びnが1であり、Rf1及びRf2がフッ素原子であり、Rf3がトリフルオロメチル基であり、Rf4が水素原子である1の塩化合物。
4.R1が、ラクトン構造を含む基である1〜3のいずれかの塩化合物。
5.M+が、下記式(A1)で表されるスルホニウム塩、下記式(A2)で表されるヨードニウム塩又は下記式(A3)で表されるアンモニウム塩である1〜4のいずれかの塩化合物。
6.1〜5のいずれかの塩化合物からなる光酸発生剤。
7.6の光酸発生剤を含む化学増幅レジスト組成物。
8.更に、下記式(a)で表される繰り返し単位及び下記式(b)で表される繰り返し単位を有するポリマーを含むベース樹脂を含む7の化学増幅レジスト組成物。
9.更に、有機溶剤を含む7又は8の化学増幅レジスト組成物。
10.更に、クエンチャーを含む7〜9のいずれかの化学増幅レジスト組成物。
11.前記クエンチャーが、下記式(1a)又は(1b)で表される化合物を含む10の化学増幅レジスト組成物。
12.前記クエンチャーが、アミン化合物を含む10の化学増幅レジスト組成物。
13.更に、6の光酸発生剤以外の、その他の光酸発生剤を含む7〜12のいずれかの化学増幅レジスト組成物。
14.前記その他の光酸発生剤が、下記式(3)又は(4)で表されるものである13の化学増幅レジスト組成物。
15.更に、水に不溶又は難溶でアルカリ現像液に可溶な界面活性剤、及び/又は水及びアルカリ現像液に不溶又は難溶な界面活性剤を含む7〜14のいずれかの化学増幅レジスト組成物。
16.7〜15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。
17.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16のパターン形成方法。
18.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16のパターン形成方法。
19.前記有機溶剤が、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18のパターン形成方法。
20.前記露光が、屈折率1.0以上の液体をレジスト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16〜19のいずれかのパターン形成方法。
21.前記レジスト膜の上に更に保護膜を形成し、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20のパターン形成方法。
本発明の塩化合物は、下記式(A)で表されるものである。
本発明の化学増幅レジスト組成物は、(A)式(A)で表される塩化合物からなる光酸発生剤を必須成分とし、その他の材料として
(B)ベース樹脂、及び
(C)有機溶剤
を含み、更に必要に応じて
(D)クエンチャー、及び
(E)式(A)で表される塩化合物以外の光酸発生剤、
(F)水に不溶又は難溶でアルカリ現像液に可溶な界面活性剤、及び/又は水及びアルカリ現像液に不溶又は難溶な界面活性剤
を含むことができる。
(B)成分のベース樹脂は、下記式(a)で表される繰り返し単位及び下記式(b)で表される繰り返し単位を含むポリマーを含むものである。
(I)式(a)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1〜60モル%、より好ましくは5〜50モル%、更に好ましくは10〜50モル%、
(II)式(b)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%、更に好ましくは50〜90モル%、
(III)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%。
本発明で使用される(C)成分の有機溶剤としては、前述した各成分及び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(PGMEA)、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(GBL)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。
本発明の化学増幅レジスト組成物は、必要に応じて、更に、クエンチャーを含んでもよい。なお、本発明においてクエンチャーとは、光酸発生剤から発生した酸をトラップする化合物を意味する。これによって、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。
本発明の化学増幅レジスト組成物は、更に、式(A)で表される塩化合物以外のその他の光酸発生剤を含んでいてもよい。前記その他の光酸発生剤としては、紫外線、遠紫外線、EB、EUV、X線、エキシマレーザー、γ線、シンクロトロン放射線等の高エネルギー線照射により酸を発生する化合物であれば、特に限定されない。好適な光酸発生剤としては、スルホニウム塩、ヨードニウム塩、スルホニルジアゾメタン、N−スルホニルオキシジカルボキシイミド、O−アリールスルホニルオキシム、O−アルキルスルホニルオキシム等の光酸発生剤等が挙げられる。これらは、1種単独で又は2種以上を混合して用いることができる。これらの光酸発生剤としては、例えば、特開2007−145797号公報の段落[0102]〜[0113]に記載のものが挙げられる。なお、ヨードニウム塩のカチオンとしてはジフェニルヨードニウム及びジ−tert−ブチルフェニルヨードニウムが好ましい。
本発明の化学増幅レジスト組成物は、(F)水に不溶又は難溶でアルカリ現像液に可溶な界面活性剤、及び/又は水及びアルカリ現像液に不溶又は難溶な界面活性剤を含んでもよい。このような界面活性剤としては、特開2010−215608号公報や特開2011−16746号公報に記載のものを参照することができる。
−C(=O)−O−Rs7
(式中、Rs7は、炭素数1〜20のフッ素化炭化水素基である。)
で表される基である。Rs6は、炭素数1〜15の1価炭化水素基又はフッ素化1価炭化水素基であり、炭素−炭素結合間に、エーテル結合(−O−)又はカルボニル基(−C(=O)−)が介在していてもよい。
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、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、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。
・IR:サーモフィッシャーサイエンティフィック社製、NICOLET 6700
・1H-NMR:日本電子(株)製ECA-500
・19F-NMR:日本電子(株)製ECA-500
・MALDI TOF-MS:日本電子(株)製S3000
[実施例1−1]PAG−1の合成
[実施例1−1−1]中間体Aの合成
IR (D-ATR): ν=3502, 3321, 3066, 2971, 1767, 1666, 1542, 1477, 1448, 1370, 1319, 1266, 1243, 1173, 1088, 1073, 1033, 990, 930, 910, 842, 750, 684, 642, 596, 553 cm-1.
MALDI TOF-MS: POSITIVE M+263(C18H15S+相当)
NEGATIVE M-464(C15H15F5NO8S-相当)
IR (D-ATR): ν= 3314, 3064, 2965, 2873, 1770, 1705, 1669, 1589, 1544, 1491, 1478, 1447, 1402, 1367, 1318, 1298, 1267, 1243, 1218, 1181, 1140, 1114, 1088, 1073, 1033, 990, 928, 909, 891, 874, 840, 751, 684, 642, 592, 554, 524 cm-1.
MALDI TOF-MS: POSITIVE M+319(C22H23S+相当)
NEGATIVE M-464(C15H15F5NO8S-相当)
[実施例1−3−1]中間体Cの合成
IR (D-ATR): ν= 3363, 3063, 2905, 2851, 2658, 1770, 1645, 1581, 1525, 1477, 1448, 1370, 1330, 1265, 1247, 1183, 1171, 1118, 1091, 1074, 1023, 996, 910, 841, 750, 684, 642, 592, 553 cm-1.
MALDI TOF-MS: POSITIVE M+263(C18H15S+相当)
NEGATIVE M-462(C17H21F5NO6S-相当)
IR (D-ATR): ν= 3310, 3066, 2972, 2908, 2853, 1778, 1727, 1672, 1545, 1477, 1448, 1369, 1326, 1270, 1240, 1172, 1104, 1077, 1038, 1010, 997, 937, 909, 842, 750, 684, 642, 592, 553cm-1.
MALDI TOF-MS: POSITIVE M+263(C18H15S+相当)
NEGATIVE M-642(C26H29F5NO10S-相当)
更に、対応する原料及び公知の有機合成方法を用い、以下に示すPAG−5〜PAG−14を合成した。
本発明の化学増幅レジスト組成物に用いるポリマーを以下に示す方法で合成した。なお、得られたポリマーの重量平均分子量(Mw)は、溶剤としてTHFを用いたゲルパーミエーションクロマトグラフィー(GPC)によりポリスチレン換算値として測定した。
各単量体の種類、配合比を変えた以外は、合成例1と同様の方法で、ポリマーP−2を合成した。ポリマーP−2のMwは8,500、Mw/Mnは1.58であった。
[実施例2−1〜2−28、比較例1−1〜1−12]
本発明の塩化合物(PAG−1〜PAG−14)、比較用光酸発生剤(PAG−A〜PAG−F)、ポリマー(P−1、P−2)、クエンチャー(Q−1〜Q−4)、及びアルカリ可溶型界面活性剤SF−1を、下記表1及び2に示す組成で、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溶液を調製し、該溶液を0.2μmのテフロン(登録商標)製フィルターでろ過することにより、化学増幅レジスト組成物を調製した。
Mw=7,700、Mw/Mn=1.82
Mw=1,500
[実施例3−1〜3−14、比較例2−1〜2−6]
シリコン基板上に反射防止膜溶液(日産化学工業(株)製ARC29A)を塗布し、200℃で60秒間ベークして反射防止膜(100nm膜厚)を形成した。前記反射防止膜上に、各レジスト組成物(R−1〜R−14、R−29〜R−34)を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のレジスト膜を作製した。これをArFエキシマレーザースキャナー((株)ニコン製、NSR-S610C、NA=1.30、二重極、Crマスク)を用いて、ウエハー上寸法がライン幅40nm、ピッチ80nmのラインアンドスペースパターン(LSパターン)を露光量とフォーカスを変化させながら(露光量ピッチ:1mJ/cm2、フォーカスピッチ:0.025μm)液浸露光を行い、露光後、表3に示す温度で60秒間ベーク(PEB)した。なお、液浸液としては水を用いた。その後、2.38質量%のTMAH水溶液で30秒間パドル現像を行い、純水でリンス、スピンドライを行い、ポジ型パターンを得た。現像後のLSパターンを、(株)日立ハイテクノロジーズ製測長SEM(CG5000)で観察し、感度、EL、MEF、LWR及び形状を、下記方法に従い評価した。結果を表3に示す。
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、これを感度とした。この値が小さいほど感度が高い。結果を表3に示す。
EL評価として、前記LSパターンにおける40nmのスペース幅の±10%(36〜44nm)の範囲内で形成される露光量から、次式によりEL(単位:%)を求めた。結果を表3に示す。
EL(%)=(|E1−E2|/Eop)×100
E1:ライン幅36nm、ピッチ80nmのLSパターンを与える最適な露光量
E2:ライン幅44nm、ピッチ80nmのLSパターンを与える最適な露光量
Eop:ライン幅40nm、ピッチ80nmのLSパターンを与える最適な露光量
ピッチは固定したまま、マスクのライン幅を変えて、Eopで照射されたそれぞれのパターンのライン幅を観察した。マスクのライン幅とパターンのライン幅の変化から、次式によりMEFの値を求めた。この値が1に近いほど性能が良好である。結果を表3に示す。
MEF=(パターンのライン幅/マスクのライン幅)−b
b:定数
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。結果を表3に示す。
Eopで照射して得たLSパターンの断面を、(株)日立ハイテクノロジーズ製SEM(S-4800)で観察し、ラインパターンの形状が矩形に近いものを良好であると評価し、一方、形状が丸くなったり、あるいはパターントップが張り出す形状(T−トップ形状)は不良であると評価した。結果を表3に示す。
[実施例4−1〜4−14、比較例3−1〜3−6]
各レジスト組成物(R−15〜R−28、R−35〜R−40)を、信越化学工業(株)製スピンオンカーボン膜ODL-180(カーボンの含有量が80質量%)を180nm、その上にケイ素含有スピンオンハードマスクSHB-A941(ケイ素の含有量が43質量%)を35nm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、ホットプレートを用いて100℃で60秒間ベークし、膜厚100nmのレジスト膜を形成した。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-S610C、NA=1.30、σ0.90/0.72、クロスポール開口35度、Azimuthally偏光照明、6%ハーフトーン位相シフトマスク、クロスポール照明)で、ウエハー上寸法が45nm、ピッチ110nmのコンタクトホールパターン(CHパターン)の露光を、露光量とフォーカスを変化(露光量ピッチ:1mJ/cm2、フォーカスピッチ:0.025μm)させながら行い、露光後、表4に示す温度で60秒間PEBした。なお、液浸液としては水を用いた。その後、酢酸n−ブチルで30秒間パドル現像を行い、4−メチル−2−ペンタノールでリンスし、スピンドライを行い、ネガ型パターンを得た。現像後のCHパターンを(株)日立ハイテクノロジーズ製測長SEM(CG4000)で観察し、感度、MEF、CDU及び焦点深度(DOF)を、下記方法に従い評価した。結果を表4に示す。
感度として、ホール寸法45nm、ピッチ110nmのCH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。結果を表4に示す。
ピッチは固定したまま、マスクの寸法を変えて、Eopで照射されたそれぞれのCHパターンを観察した。マスクの寸法とCHパターンの寸法の変化から、次式によりMEFの値を求めた。この値が1に近いほど性能が良好である。結果を表4に示す。
MEF=(パターンの寸法/マスクの寸法)−b
b:定数
Eopで照射して得たCHパターンを、同一露光量ショット内10箇所(1箇所につき9個のCHパターン)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、CHパターンの寸法均一性が優れる。結果を表4に示す。
Eopで照射して得たCHパターンにおける45nmの寸法の±10%(41〜49nm)の範囲で形成されるフォーカス範囲を求めた。この値が大きいほど、焦点深度が広い。結果を表4に示す。
1.下記式(A)で表される塩化合物。
2.m及びnが1であり、Rf1及びRf2がフッ素原子であり、Rf3及びRf4が水素原子である1の塩化合物。
3.m及びnが1であり、Rf1及びRf2がフッ素原子であり、Rf3がトリフルオロメチル基であり、Rf4が水素原子である1の塩化合物。
4.R1が、ラクトン構造を含む基である1〜3のいずれかの塩化合物。
5.M+が、下記式(A1)で表されるスルホニウムカチオン、下記式(A2)で表されるヨードニウムカチオン又は下記式(A3)で表されるアンモニウムカチオンである1〜4のいずれかの塩化合物。
6.1〜5のいずれかの塩化合物からなる光酸発生剤。
7.6の光酸発生剤を含む化学増幅レジスト組成物。
8.更に、下記式(a)で表される繰り返し単位及び下記式(b)で表される繰り返し単位を有するポリマーを含むベース樹脂を含む7の化学増幅レジスト組成物。
9.更に、有機溶剤を含む7又は8の化学増幅レジスト組成物。
10.更に、クエンチャーを含む7〜9のいずれかの化学増幅レジスト組成物。
11.前記クエンチャーが、下記式(1a)又は(1b)で表される化合物を含む10の化学増幅レジスト組成物。
12.前記クエンチャーが、アミン化合物を含む10の化学増幅レジスト組成物。
13.更に、6の光酸発生剤以外の、その他の光酸発生剤を含む7〜12のいずれかの化学増幅レジスト組成物。
14.前記その他の光酸発生剤が、下記式(3)又は(4)で表されるものである13の化学増幅レジスト組成物。
15.更に、水に不溶又は難溶でアルカリ現像液に可溶な界面活性剤、及び/又は水及びアルカリ現像液に不溶又は難溶な界面活性剤を含む7〜14のいずれかの化学増幅レジスト組成物。
16.7〜15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。
17.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16のパターン形成方法。
18.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16のパターン形成方法。
19.前記有機溶剤が、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18のパターン形成方法。
20.前記露光が、屈折率1.0以上の液体をレジスト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16〜19のいずれかのパターン形成方法。
21.前記レジスト膜の上に更に保護膜を形成し、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20のパターン形成方法。
Claims (21)
- 下記式(A)で表される塩化合物。
- m及びnが1であり、Rf1及びRf2がフッ素原子であり、Rf3及びRf4が水素原子である請求項1記載の塩化合物。
- m及びnが1であり、Rf1及びRf2がフッ素原子であり、Rf3がトリフルオロメチル基であり、Rf4が水素原子である請求項1記載の塩化合物。
- R1が、ラクトン構造を含む基である請求項1〜3のいずれか1項記載の塩化合物。
- M+が、下記式(A1)で表されるスルホニウム塩、下記式(A2)で表されるヨードニウム塩又は下記式(A3)で表されるアンモニウム塩である請求項1〜4のいずれか1項記載の塩化合物。
- 請求項1〜5のいずれか1項記載の塩化合物からなる光酸発生剤。
- 請求項6記載の光酸発生剤を含む化学増幅レジスト組成物。
- 更に、下記式(a)で表される繰り返し単位及び下記式(b)で表される繰り返し単位を有するポリマーを含むベース樹脂を含む請求項7記載の化学増幅レジスト組成物。
- 更に、有機溶剤を含む請求項7又は8記載の化学増幅レジスト組成物。
- 更に、クエンチャーを含む請求項7〜9のいずれか1項記載の化学増幅レジスト組成物。
- 前記クエンチャーが、下記式(1a)又は(1b)で表される化合物を含む請求項10記載の化学増幅レジスト組成物。
- 前記クエンチャーが、アミン化合物を含む請求項10記載の化学増幅レジスト組成物。
- 更に、請求項6記載の光酸発生剤以外の、その他の光酸発生剤を含む請求項7〜12のいずれか1項記載の化学増幅レジスト組成物。
- 前記その他の光酸発生剤が、下記式(3)又は(4)で表されるものである請求項13記載の化学増幅レジスト組成物。
- 更に、水に不溶又は難溶でアルカリ現像液に可溶な界面活性剤、及び/又は水及びアルカリ現像液に不溶又は難溶な界面活性剤を含む請求項7〜14のいずれか1項記載の化学増幅レジスト組成物。
- 請求項7〜15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16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16記載のパターン形成方法。
- 前記有機溶剤が、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18記載のパターン形成方法。
- 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16〜19のいずれか1項記載のパターン形成方法。
- 前記レジスト膜の上に更に保護膜を形成し、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20記載のパターン形成方法。
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KR102315790B1 (ko) | 2021-10-20 |
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