CN115960296A - Resin and application of ArF immersed photoresist containing resin - Google Patents
Resin and application of ArF immersed photoresist containing resin Download PDFInfo
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- CN115960296A CN115960296A CN202111172205.4A CN202111172205A CN115960296A CN 115960296 A CN115960296 A CN 115960296A CN 202111172205 A CN202111172205 A CN 202111172205A CN 115960296 A CN115960296 A CN 115960296A
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- 229920002120 photoresistant polymer Polymers 0.000 title claims abstract description 137
- 239000011347 resin Substances 0.000 title claims abstract description 131
- 229920005989 resin Polymers 0.000 title claims abstract description 131
- 239000000203 mixture Substances 0.000 claims abstract description 86
- 238000000034 method Methods 0.000 claims abstract description 40
- 238000007654 immersion Methods 0.000 claims abstract description 12
- 239000011248 coating agent Substances 0.000 claims abstract description 6
- 238000000576 coating method Methods 0.000 claims abstract description 6
- 239000000178 monomer Substances 0.000 claims description 172
- 150000001875 compounds Chemical class 0.000 claims description 101
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 88
- 239000002904 solvent Substances 0.000 claims description 30
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 21
- 238000006116 polymerization reaction Methods 0.000 claims description 21
- 238000009826 distribution Methods 0.000 claims description 19
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 239000004094 surface-active agent Substances 0.000 claims description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 15
- 239000003960 organic solvent Substances 0.000 claims description 12
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 9
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 230000000379 polymerizing effect Effects 0.000 claims description 8
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 238000000671 immersion lithography Methods 0.000 claims description 6
- 239000002994 raw material Substances 0.000 claims description 6
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 238000011161 development Methods 0.000 claims description 4
- 238000010894 electron beam technology Methods 0.000 claims description 4
- -1 i-propylPropyl Chemical group 0.000 claims description 4
- 239000003999 initiator Substances 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 230000005855 radiation Effects 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 150000007942 carboxylates Chemical class 0.000 claims description 2
- 239000004210 ether based solvent Substances 0.000 claims description 2
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims description 2
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 238000010791 quenching Methods 0.000 claims description 2
- 230000000171 quenching effect Effects 0.000 claims description 2
- 238000004528 spin coating Methods 0.000 claims description 2
- 238000005507 spraying Methods 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 2
- 238000007598 dipping method Methods 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- 239000000758 substrate Substances 0.000 abstract description 6
- 230000035945 sensitivity Effects 0.000 abstract description 5
- 238000001259 photo etching Methods 0.000 abstract description 3
- 230000000052 comparative effect Effects 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 7
- 230000001681 protective effect Effects 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 238000000206 photolithography Methods 0.000 description 6
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 5
- 239000011148 porous material Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 4
- 206010034972 Photosensitivity reaction Diseases 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
- 230000036211 photosensitivity Effects 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-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
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000012986 chain transfer agent Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 3
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 2
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 2
- LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- UYWQUFXKFGHYNT-UHFFFAOYSA-N Benzylformate Chemical compound O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- CRZQGDNQQAALAY-UHFFFAOYSA-N Methyl benzeneacetate Chemical compound COC(=O)CC1=CC=CC=C1 CRZQGDNQQAALAY-UHFFFAOYSA-N 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- NMJJFJNHVMGPGM-UHFFFAOYSA-N butyl formate Chemical compound CCCCOC=O NMJJFJNHVMGPGM-UHFFFAOYSA-N 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 2
- RPUSRLKKXPQSGP-UHFFFAOYSA-N methyl 3-phenylpropanoate Chemical compound COC(=O)CCC1=CC=CC=C1 RPUSRLKKXPQSGP-UHFFFAOYSA-N 0.000 description 2
- 229940095102 methyl benzoate Drugs 0.000 description 2
- BHIWKHZACMWKOJ-UHFFFAOYSA-N methyl isobutyrate Chemical compound COC(=O)C(C)C BHIWKHZACMWKOJ-UHFFFAOYSA-N 0.000 description 2
- 229940057867 methyl lactate Drugs 0.000 description 2
- HNBDRPTVWVGKBR-UHFFFAOYSA-N n-pentanoic acid methyl ester Natural products CCCCC(=O)OC HNBDRPTVWVGKBR-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- VKCYHJWLYTUGCC-UHFFFAOYSA-N nonan-2-one Chemical compound CCCCCCCC(C)=O VKCYHJWLYTUGCC-UHFFFAOYSA-N 0.000 description 2
- PGMYKACGEOXYJE-UHFFFAOYSA-N pentyl acetate Chemical compound CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 2
- MDHYEMXUFSJLGV-UHFFFAOYSA-N phenethyl acetate Chemical compound CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 2
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 2
- 238000002791 soaking Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
- ULPMRIXXHGUZFA-UHFFFAOYSA-N (R)-4-Methyl-3-hexanone Natural products CCC(C)C(=O)CC ULPMRIXXHGUZFA-UHFFFAOYSA-N 0.000 description 1
- LEEANUDEDHYDTG-UHFFFAOYSA-N 1,2-dimethoxypropane Chemical compound COCC(C)OC LEEANUDEDHYDTG-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- JEIHSRORUWXJGF-UHFFFAOYSA-N 1-[(2-methylpropan-2-yl)oxy]propan-2-yl acetate Chemical compound CC(=O)OC(C)COC(C)(C)C JEIHSRORUWXJGF-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
- 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 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- AVMSWPWPYJVYKY-UHFFFAOYSA-N 2-Methylpropyl formate Chemical compound CC(C)COC=O AVMSWPWPYJVYKY-UHFFFAOYSA-N 0.000 description 1
- QGLVWTFUWVTDEQ-UHFFFAOYSA-N 2-chloro-3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1Cl QGLVWTFUWVTDEQ-UHFFFAOYSA-N 0.000 description 1
- WBPAQKQBUKYCJS-UHFFFAOYSA-N 2-methylpropyl 2-hydroxypropanoate Chemical compound CC(C)COC(=O)C(C)O WBPAQKQBUKYCJS-UHFFFAOYSA-N 0.000 description 1
- PFCHFHIRKBAQGU-UHFFFAOYSA-N 3-hexanone Chemical compound CCCC(=O)CC PFCHFHIRKBAQGU-UHFFFAOYSA-N 0.000 description 1
- JSGVZVOGOQILFM-UHFFFAOYSA-N 3-methoxy-1-butanol Chemical compound COC(C)CCO JSGVZVOGOQILFM-UHFFFAOYSA-N 0.000 description 1
- MFKRHJVUCZRDTF-UHFFFAOYSA-N 3-methoxy-3-methylbutan-1-ol Chemical compound COC(C)(C)CCO MFKRHJVUCZRDTF-UHFFFAOYSA-N 0.000 description 1
- CRORGGSWAKIXSA-UHFFFAOYSA-N 3-methylbutyl 2-hydroxypropanoate Chemical compound CC(C)CCOC(=O)C(C)O CRORGGSWAKIXSA-UHFFFAOYSA-N 0.000 description 1
- VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-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
- MRABAEUHTLLEML-UHFFFAOYSA-N Butyl lactate Chemical compound CCCCOC(=O)C(C)O MRABAEUHTLLEML-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- ZFDIRQKJPRINOQ-HWKANZROSA-N Ethyl crotonate Chemical compound CCOC(=O)\C=C\C ZFDIRQKJPRINOQ-HWKANZROSA-N 0.000 description 1
- XXRCUYVCPSWGCC-UHFFFAOYSA-N Ethyl pyruvate Chemical compound CCOC(=O)C(C)=O XXRCUYVCPSWGCC-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
- XYVQFUJDGOBPQI-UHFFFAOYSA-N Methyl-2-hydoxyisobutyric acid Chemical compound COC(=O)C(C)(C)O XYVQFUJDGOBPQI-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- NLAMRLZPVVKXTK-SNAWJCMRSA-N [(e)-but-1-enyl] acetate Chemical compound CC\C=C\OC(C)=O NLAMRLZPVVKXTK-SNAWJCMRSA-N 0.000 description 1
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- DULCUDSUACXJJC-UHFFFAOYSA-N benzeneacetic acid ethyl ester Natural products CCOC(=O)CC1=CC=CC=C1 DULCUDSUACXJJC-UHFFFAOYSA-N 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 229940007550 benzyl acetate Drugs 0.000 description 1
- 239000005380 borophosphosilicate glass Substances 0.000 description 1
- 239000001191 butyl (2R)-2-hydroxypropanoate Substances 0.000 description 1
- 229940043232 butyl acetate Drugs 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- GFUIDHWFLMPAGY-UHFFFAOYSA-N ethyl 2-hydroxy-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)O GFUIDHWFLMPAGY-UHFFFAOYSA-N 0.000 description 1
- BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 229940117360 ethyl pyruvate Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- XKYICAQFSCFURC-UHFFFAOYSA-N isoamyl formate Chemical compound CC(C)CCOC=O XKYICAQFSCFURC-UHFFFAOYSA-N 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- MCVVUJPXSBQTRZ-ONEGZZNKSA-N methyl (e)-but-2-enoate Chemical compound COC(=O)\C=C\C MCVVUJPXSBQTRZ-ONEGZZNKSA-N 0.000 description 1
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
- MBAHGFJTIVZLFB-UHFFFAOYSA-N methyl pent-2-enoate Chemical compound CCC=CC(=O)OC MBAHGFJTIVZLFB-UHFFFAOYSA-N 0.000 description 1
- 238000005459 micromachining Methods 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- GXOHBWLPQHTYPF-UHFFFAOYSA-N pentyl 2-hydroxypropanoate Chemical compound CCCCCOC(=O)C(C)O GXOHBWLPQHTYPF-UHFFFAOYSA-N 0.000 description 1
- 230000010363 phase shift Effects 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-M phenylacetate Chemical compound [O-]C(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-M 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- ILVGAIQLOCKNQA-UHFFFAOYSA-N propyl 2-hydroxypropanoate Chemical compound CCCOC(=O)C(C)O ILVGAIQLOCKNQA-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 230000007261 regionalization Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000000725 suspension Substances 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
- JAELLLITIZHOGQ-UHFFFAOYSA-N tert-butyl propanoate Chemical compound CCC(=O)OC(C)(C)C JAELLLITIZHOGQ-UHFFFAOYSA-N 0.000 description 1
- ZFDIRQKJPRINOQ-UHFFFAOYSA-N transbutenic acid ethyl ester Natural products CCOC(=O)C=CC ZFDIRQKJPRINOQ-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Materials For Photolithography (AREA)
Abstract
The invention discloses a resin and application of an ArF immersion photoresist containing the resin. The method for forming the photoetching pattern comprises the following steps: s1: coating the photoresist composition on the surface of a substrate, and baking to form a photoresist layer; s2: exposing the photoresist layer formed in the step S1; s3: baking the photoresist layer exposed in the step S2; s4: and developing the photoresist layer baked in the step S3. The photoresist containing the resin has the advantages of high resolution, high sensitivity and low line width roughness.
Description
Technical Field
The invention relates to a resin and application of an ArF immersion photoresist containing the resin.
Background
The photolithography technique is a fine processing technique for transferring a pattern designed on a mask plate to a pattern on a substrate by using the chemical sensitivity of a photolithography material (particularly a photoresist) under the action of visible light, ultraviolet rays, electron beams and the like through the processes of exposure, development, etching and the like. The photoresist material (specifically referred to as photoresist), also called photoresist, is the most critical functional chemical material involved in the photolithography technology, and its main components are resin, photo Acid Generator (PAG), and corresponding additives and solvents. The photo-acid generator is a light-sensitive compound, which is decomposed under illumination to generate acid, and the generated acid can make acid-sensitive resin generate decomposition or cross-linking reaction, so that the dissolution contrast of the illuminated part and the non-illuminated part in a developing solution is increased, and the photo-acid generator can be used in the technical field of pattern micro-machining.
Three important parameters of the photoresist include resolution, sensitivity, line width roughness, which determine the process window of the photoresist during chip fabrication. With the increasing performance of semiconductor chips, the integration level of integrated circuits is increased exponentially, and the patterns in the integrated circuits are continuously reduced. In order to make patterns with smaller dimensions, the performance indexes of the three photoresists must be improved. The use of a short wavelength light source in a photolithography process can improve the resolution of the photoresist according to the rayleigh equation. The light source wavelength of the photolithography process is developed from 365nm (I-line) to 248nm (KrF), 193nm (ArF), and 13nm (EUV). In order to improve the sensitivity of the photoresist, the current KrF, arF and EUV photoresists are mainly made of chemically amplified photosensitive resin. Thus, photosensitizers (photoacid generators) compatible with chemically amplified photosensitive resins are widely used in high-end photoresists.
As the photolithography process is gradually developed, the process complexity is increased to 193nm immersion process, and higher requirements are put on the resist (i.e. photoresist). Developing a photoresist capable of improving resolution, sensitivity and line width roughness becomes a problem to be solved urgently in the industry.
Disclosure of Invention
The invention aims to overcome the defect that the number of methods for forming photoetching patterns is small in the prior art, and provides a resin and application of an ArF immersion photoresist containing the resin. The photolithographic pattern formed by the method for forming the photolithographic pattern of the invention has at least the following advantages: excellent photosensitivity, good depth of focus and good line width uniformity.
The invention provides a method for forming a photoetching pattern, which comprises the following steps:
s1: coating the photoresist composition on the surface of a substrate, and baking to form a photoresist layer;
s2: exposing the photoresist layer formed in the step S1;
s3: baking the photoresist layer exposed in the step S2;
s4: developing the photoresist layer baked in the step S3;
the photoresist composition is prepared from the following raw materials in parts by weight: 75-95 parts of resin, 1.0-10 parts of photoacid generator, 1000-2000 parts of solvent, 0.5-3.0 parts of quencher and surfactant;
the resin is obtained by polymerizing the following monomers in parts by weight: 40-50 parts of monomer A, 1-7.5 parts of monomer B, 0.25-2.5 parts of monomer C and 0.25-2.5 parts of monomer D;
wherein R is 1 Is C 1-10 Alkyl groups of (a);
R 2 is H or C 1-10 Alkyl groups of (a);
R 3 is C 1-10 Alkyl groups of (a);
R 4 is C 2-4 Alkenyl of (a);
R 5 and R 6 Independently is H or C 1-5 Alkyl group of (1).
In some embodiments, R 1 In (b), the C 1-10 Alkyl of (A) is C 1-5 The alkyl group of (b) is preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group or a tert-butyl group.
In some embodiments, R 2 In (b), the C 1-10 Alkyl of (A) is C 1-5 The alkyl group of (a) is,preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl.
In some embodiments, R 3 In (b), the C 1-10 Alkyl of (A) is C 1-5 The alkyl group of (b) is preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group or a tert-butyl group.
In some embodiments, R 4 In (b), the C 2-4 Alkenyl of (A) is C 2-3 The alkenyl group of (1) is preferably an ethenyl group or an isopropenyl group.
In some embodiments, R 5 In (b), the C 1-5 The alkyl group of (b) is preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group or a tert-butyl group.
In some embodiments, R 2 Is C 1-10 Alkyl group of (1).
In some embodiments, R 5 And R 6 Is C 1-10 The alkyl group of (1).
In some embodiments, the resin has a weight average molecular weight (Mw) of 5000 to 10000, e.g., 5600 to 9800.
In one embodiment of the invention, the resin has a molecular weight distribution coefficient (Mw/Mn) of from 1.0 to 2.0, for example from 1.2 to 2.0.
The molecular weight distribution coefficient refers to a ratio of the weight average molecular weight to the number average molecular weight of the resin.
In some embodiments, the portion of monomer A is from 40 to 47.5 (e.g., 41.5, 45, or 46), such as from 41.5 to 45.
In some embodiments, the portion of monomer B is from 2.5 to 4 parts.
In some embodiments, the portion of monomer C is from 0.25 to 1.75 parts (e.g., 0.5, 0.75, 1.25, 1.5, or 1.75), such as from 0.5 to 1.25 parts.
In some embodiments, the portion of monomer D is from 0.5 to 1.75 parts (e.g., 0.75 or 1.25), such as from 0.5 to 1.25 parts.
In some embodiments, the portion of monomer a is from 40 to 47.5 parts;
the part of the monomer C is 0.25-1.75;
the part of the monomer D is 0.5-1.75;
R 2 is C 1-10 Alkyl groups of (a);
R 5 and R 6 Independently is C 1-5 The alkyl group of (1).
the part of the monomer B is 2.5-4 parts;
In some embodiments, the resin is any one of resins 1 to 8 obtained by polymerizing the following monomers in parts by weight:
resin 1:41.5 parts of monomer A, 5 parts of monomer B, 1.25 parts of monomer C and 1.25 parts of monomer D; the weight average molecular weight is 7100, and the molecular weight distribution coefficient is 1.2;
resin 2:45 parts of monomer A, 4 parts of monomer B, 0.5 part of monomer C and 0.5 part of monomer D; the weight average molecular weight is 9800, and the molecular weight distribution coefficient is 1.3;
resin 3:45 parts of monomer A, 4 parts of monomer B, 0.25 part of monomer C and 0.75 part of monomer D; the weight average molecular weight is 8500, and the molecular weight distribution coefficient is 1.2;
resin 4:45 parts of monomer A, 2.5 parts of monomer B, 1.25 parts of monomer C and 1.25 parts of monomer D; the weight average molecular weight is 6400, the molecular weight distribution coefficient is 2;
resin 5:41.5 parts of monomer A, 4 parts of monomer B, 1.75 parts of monomer C and 1.75 parts of monomer D; the weight average molecular weight is 5600, and the molecular weight distribution coefficient is 1.9;
resin 6:47.5 parts of monomer A, 1 part of monomer B, 0.75 part of monomer C and 0.75 part of monomer D; the weight average molecular weight is 8700, and the molecular weight distribution coefficient is 2;
resin 7:40 parts of monomer A, 7.5 parts of monomer B, 1.5 parts of monomer C and 1 part of monomer D; the weight average molecular weight is 9300, the molecular weight distribution coefficient is 1.6;
resin 8:46 parts of monomer A, 2.5 parts of monomer B, 0.75 part of monomer C and 0.75 part of monomer D; the weight average molecular weight is 8100, and the molecular weight distribution coefficient is 1.7;
In some embodiments, the resin is prepared by: polymerizing 40-50 parts by weight of monomer A, 1-7.5 parts by weight of monomer B, 0.25-2.5 parts by weight of monomer C and 0.25-2.5 parts by weight of monomer D in an organic solvent to obtain the resin;
the parts and kinds of the monomers A, the parts and kinds of the monomers B, the parts and kinds of the monomers C and the parts and kinds of the monomers D are the same as those described above.
The conditions and operations of the polymerization reaction may be those conventional in the art for such reactions, with the following conditions and operations being particularly preferred in the present invention:
in the polymerization reaction, the weight ratio of the total weight of the monomer a, the monomer B, the monomer C, and the monomer D to the organic solvent is preferably 0.7 to 1.2, for example, 1.
In the polymerization reaction, the organic solvent is preferably one or more of an aromatic hydrocarbon solvent (e.g., toluene or benzene), an ether solvent (e.g., tetrahydrofuran (THF), diethyl ether or dioxane), methyl Ethyl Ketone (MEK), propylene Glycol Monomethyl Ether Acetate (PGMEA) and γ -butyrolactone, e.g., propylene glycol monomethyl ether acetate.
The polymerization is preferably initiated in the presence of a free-radical initiator or by means of heat, for example by means of heat.
When the polymerization is initiated in the presence of a radical initiator, the radical initiator is preferably one or more of 2,2 '-Azobisisobutyronitrile (AIBN), 2' -azobis (2, 4-dimethylvaleronitrile), 2-azobis (methyl 2-methylpropionate), benzoyl peroxide and lauroyl peroxide.
When the polymerization is initiated by heating, the polymerization temperature is preferably 50 to 150 deg.C, more preferably 60 to 100 deg.C, for example 70 deg.C.
In the polymerization, the time of the polymerization is preferably 2 to 6 hours, for example, 3 hours.
Preferably, the polymerization reaction comprises the following steps:
step 1: mixing the monomer A, the monomer B, the monomer C, the monomer D and propylene glycol monomethyl ether acetate to obtain a mixture;
the weight ratio of the total weight of monomer a, monomer B, monomer C, and monomer D to the propylene glycol monomethyl ether acetate is from 5 to 3 (e.g., 10;
step 2: carrying out polymerization reaction on the mixture obtained in the step 1 in propylene glycol monomethyl ether acetate to obtain the resin;
the ratio of the total weight of the monomer A, the monomer B, the monomer C and the monomer D to the total weight of the propylene glycol monomethyl ether acetate (i.e., the sum of the weight of the propylene glycol monomethyl ether acetate in step 1 and the weight of the propylene glycol monomethyl ether acetate in step 2) is from 0.7 to 1.2;
the polymerization temperature is 60-100 ℃.
In the polymerization reaction, any known chain transfer agent (e.g., dodecanethiol or 2-mercaptoethanol) may be added for the purpose of controlling the molecular weight. The amount of the chain transfer agent added is preferably 0.01 to 10mol% (the amount of the chain transfer agent may be based on the total moles of the monomers to be polymerized).
After the polymerization reaction is finished, the post-treatment of the polymerization reaction is preferably as follows: cooling, precipitation of solid (e.g. addition of methanol to precipitate solid), filtration and drying (e.g. vacuum drying at 40 ℃ for 24 hours).
In the photoresist composition, the resin is preferably 85-95 parts, for example 90 parts.
In the photoresist composition, the portion of the photoacid generator is preferably 3 to 10 portions, for example, 5 portions or 7 portions.
In the photoresist composition, the photoacid generator may be a photoacid generator conventional in the art, and preferably has a structure represented by formula (I):
X + Y -
(I),
In the photoresist composition, the solvent is preferably used in an amount of 1200 to 1600 parts, for example 1500 parts or 1600 parts.
In the photoresist composition, the solvent may be any known solvent conventionally used in photoresists, especially chemically amplified photoresist compositions. The solvent is preferably one or more of a ketone solvent (e.g., cyclohexanone and/or methyl-2-n-amyl ketone), a monohydric alcohol solvent (e.g., one or more of 3-methoxybutanol, 3-methyl-3-methoxybutanol, 1-methoxy-2-propanol, and 1-ethoxy-2-propanol), a glycol solvent (e.g., diacetone alcohol), an ether solvent (e.g., one or more of propylene glycol monomethyl ether, ethylene glycol monomethyl ether, propylene glycol monoethyl ether, ethylene glycol monoethyl ether, propylene glycol dimethyl ether, and diethylene glycol dimethyl ether), and an ester solvent (e.g., one or more of Propylene Glycol Monomethyl Ether Acetate (PGMEA), propylene glycol monoethyl ether acetate, methyl lactate, ethyl pyruvate, butyl acetate, methyl 3-methoxypropionate, ethyl 3-ethoxypropionate, t-butyl acetate, t-butyl propionate, propylene glycol mono-t-butyl ether acetate, γ -butyrolactone);
more preferably one or more of ketone solvents, ether solvents and ester solvents, for example one or more of cyclohexanone, ethylene glycol monoethyl ether and gamma-butyrolactone.
In the photoresist composition, the quencher is preferably used in an amount of 0.8 to 2 parts, for example 1.5 parts.
In the photoresist composition, the quencher may be a quencher conventional in the art, preferably one or more of amine-containing compounds (e.g., primary, secondary and tertiary amine compounds, specifically amine compounds having hydroxyl, ether, ester, lactone, cyano or sulfonate groups), sulfonates and carboxylates, more preferably sulfonates, and further preferably compounds of formula Q1 and/or compounds of formula Q2 as follows;
protection with amine-containing compounds is effective, particularly when the photoresist composition also includes a base labile component.
The amount of the surfactant in the photoresist composition may be that which is conventional in the art for such photoresists, and is preferably 0.1 to 0.2 parts, for example 0.15 parts, in parts by weight.
In the photoresist composition, the surfactant may be a surfactant conventional in the art (a surfactant insoluble or substantially insoluble in water and soluble in an alkaline developer, and/or a surfactant insoluble or substantially insoluble in water and an alkaline developer), preferably one or more of FC-4430 (from 3M), S-381 (from AGC Seimi chemical), E1004 (from Air Products), KH-20 and KH-30 (from Asahi Glass), more preferably KH-20 and/or KH-30.
the solvent is one or more of cyclohexanone (S1), ethylene glycol monoethyl ether (S2) and gamma-butyrolactone (S3);
The surfactant is KH-20 and/or KH-30.
In some embodiments, the photoresist is prepared from the following raw materials in parts by weight: the resin as described above (including the kind and part of the resin), the photoacid generator as described above (including the kind and part of the photoacid generator), the solvent as described above (including the kind and part of the solvent), the quencher as described above (including the kind and part of the quencher), and the surfactant as described above (including the kind and part of the surfactant).
In some embodiments, the photoresist composition is any one of the following photoresist compositions prepared from the following raw materials in parts by weight:
photoresist composition 1:85 parts of resin 1, 7 parts of compound shown as formula X1Y1, 1500 parts of cyclohexanone (S1), 2 parts of compound shown as formula Q1 and 0.15 part of KH-30;
photoresist composition 2:75 parts of the resin 1,1 part of the compound shown in the formula X1Y1, 1000 parts of cyclohexanone (S1), 0.5 part of the compound shown in the formula Q1 and 0.1 part of KH-30;
photoresist composition 3:80 parts of resin 1,3 parts of compound shown as a formula X1Y1, 1200 parts of cyclohexanone (S1), 0.8 part of compound shown as a formula Q1 and 0.12 part of KH-30;
photoresist composition 4:90 parts of resin 1, 5 parts of compound shown as a formula X1Y1, 1600 parts of cyclohexanone (S1), 1.5 parts of compound shown as a formula Q1 and 0.16 part of KH-30;
photoresist composition 5:95 parts of resin 1, 10 parts of compound shown as a formula X1Y1, 2000 parts of cyclohexanone, 3 parts of compound shown as a formula Q1 and 0.2 part of KH-30;
photoresist composition 6:85 parts of resin 1, 7 parts of compound shown as formula X1Y3, 1500 parts of cyclohexanone (S1), 2 parts of compound shown as formula Q1 and 0.15 part of KH-30;
photoresist composition 7:85 parts of resin 1, 7 parts of compound shown as a formula X2Y5, 1500 parts of cyclohexanone (S1), 2 parts of compound shown as a formula Q1 and 0.15 part of KH-30;
photoresist composition 8:85 parts of resin 1, 7 parts of compound shown as formula X3Y6, 1500 parts of cyclohexanone (S1), 2 parts of compound shown as formula Q1 and 0.15 part of KH-30;
photoresist composition 9:85 parts of resin 1, 7 parts of compound shown as a formula X4Y4, 1500 parts of cyclohexanone (S1), 2 parts of compound shown as a formula Q1 and 0.15 part of KH-30;
photoresist composition 10:85 parts of resin 1, 7 parts of compound shown as a formula X5Y8, 1500 parts of cyclohexanone (S1), 2 parts of compound shown as a formula Q1 and 0.15 part of KH-30;
photoresist composition 11:85 parts of resin 1, 7 parts of compound shown as formula X1Y8, 1500 parts of cyclohexanone (S1), 2 parts of compound shown as formula Q1 and 0.15 part of KH-30;
photoresist composition 12:85 parts of resin 1, 7 parts of compound shown as a formula X2Y7, 1500 parts of cyclohexanone (S1), 2 parts of compound shown as a formula Q1 and 0.15 part of KH-30;
photoresist composition 13:85 parts of resin 1, 7 parts of compound shown as a formula X1Y1, 1500 parts of ethylene glycol monoethyl ether (S2), 2 parts of compound shown as a formula Q1 and 0.15 part of KH-30;
photoresist composition 14:85 parts of resin 1, 7 parts of compound shown as a formula X1Y1, 1500 parts of gamma-butyrolactone (S3), 2 parts of compound shown as a formula Q1 and 0.15 part of KH-30;
photoresist composition 15:85 parts of resin 1, 7 parts of compound shown as formula X1Y1, 1500 parts of cyclohexanone (S1), 2 parts of compound shown as formula Q2 and 0.15 part of KH-30;
photoresist composition 16:85 parts of the resin 1, 7 parts of the compound shown in the formula X1Y1, 1500 parts of gamma-butyrolactone (S3), 2 parts of the compound shown in the formula Q1 and 0.15 part of KH-20;
photoresist composition 17:85 parts of resin 2, 7 parts of compound shown as formula X1Y1, 1500 parts of cyclohexanone (S1), 2 parts of compound shown as formula Q1 and 0.15 part of KH-30;
photoresist composition 18:85 parts of resin 3, 7 parts of compound shown as formula X1Y1, 1500 parts of cyclohexanone (S1), 2 parts of compound shown as formula Q1 and 0.15 part of KH-30;
photoresist composition 19:85 parts of the resin 4, 7 parts of the compound shown in the formula X1Y1, 1500 parts of cyclohexanone (S1), 2 parts of the compound shown in the formula Q1 and 0.15 part of KH-30;
photoresist composition 20:85 parts of resin 5, 7 parts of compound shown as formula X1Y1, 1500 parts of cyclohexanone (S1), 2 parts of compound shown as formula Q1 and 0.15 part of KH-30;
photoresist composition 21:85 parts of resin 6, 7 parts of compound shown as formula X1Y1, 1500 parts of cyclohexanone (S1), 2 parts of compound shown as formula Q1 and 0.15 part of KH-30;
photoresist composition 22:85 parts of the resin 7, 7 parts of the compound shown in the formula X1Y1, 1500 parts of cyclohexanone (S1), 2 parts of the compound shown in the formula Q1 and 0.15 part of KH-30;
photoresist composition 23:85 parts of resin 8, 7 parts of compound shown as formula X1Y1, 1500 parts of cyclohexanone (S1), 2 parts of compound shown as formula Q1 and 0.15 part of KH-30.
In the method for forming a lithographic pattern, in S1, the substrate may be a substrate for integrated circuit fabrication (e.g., si, siO) 2 One or more of SiN, siON, tiN, WSi, BPSG, SOG, and organic antireflection film) or a base material for mask circuit fabrication (e.g., cr, crO, crON, moSi) 2 And SiO 2 One or more of).
In the method for forming a lithographic pattern, in S1, the coating manner may be a conventional coating manner used in the art for forming a lithographic pattern, such as spin coating.
In the method for forming a photolithographic pattern, in S1, the baking temperature may be a conventional baking temperature used in the art for forming a photolithographic pattern, for example, 60 to 200 ℃.
In the method for forming a lithographic pattern, in S1, the baking time may be a conventional baking time used in the art for forming a lithographic pattern, such as 1-10 minutes, and further such as 1 minute.
In the method of forming a photoresist pattern, in S1, the photoresist layer may have a thickness of 0.05 to 2 μm, for example, 100nm.
In the method for forming a photolithographic pattern, the exposure is performed under a conventional operation in the art for forming a photolithographic pattern, such as high-energy radiation (e.g., krF excimer laser, arF excimer laser, or EUV), wherein the exposure dose may be 1-200mJ/cm 2 (e.g., 10-100mJ/cm 2 ) (ii) a Further, for example, electron beam exposure is employed, wherein the exposure dose may be in the range of 0.1 to 100. Mu.C/cm 2 (e.g., 0.5-50. Mu.C/cm) 2 ) (ii) a Exposure is also accomplished, for example, by immersion lithography in which a liquid having a refractive index of at least 1.0 (e.g., water) is provided between the projection lens and the photoresist layer. In the case of immersion lithography, a protective film insoluble in water may be formed on the photoresist layer.
Among them, when a water-insoluble protective film used for immersion lithography is used to prevent any component from leaching out of a photoresist layer and improve water slipperiness (water slide) at the surface of the photoresist layer, the protective film is generally classified into two types. The first type is an organic solvent strippable protective film, which must be stripped with an organic solvent that does not dissolve the photoresist layer prior to alkaline development. The second type is an alkali-soluble protective film that is soluble in an alkali developer so that it can be removed simultaneously with the removal of the dissolved regions of the photoresist layer. The second type of protective film preferably contains a material having, as a base, a resin having a residue of 1,1,1,3, 3-hexafluoro-2-propanol, which is insoluble in water and soluble in an alkaline developer, in an alcohol solvent of at least 4 carbon atoms, an ether solvent of 8 to 12 carbon atoms, or a mixture thereof. Alternatively, the aforementioned surfactant that is insoluble in water and soluble in an alkaline developer may be soluble in an alcohol solvent of at least 4 carbon atoms, an ether solvent of 8 to 12 carbon atoms, or a mixture thereof, to form a material from which the second type of protective film is formed.
In the method for forming a photolithographic pattern, in S3, the baking temperature may be a conventional baking temperature used in the art for forming a photolithographic pattern, such as 60-150 ℃, such as 80-140 ℃, and further such as 95 ℃.
In the method for forming a photolithographic pattern, in S3, the baking time may be a conventional baking time used in the art for forming a photolithographic pattern, such as 1-5 minutes, and further such as 1 minute.
In the method for forming a lithographic pattern, in S4, the developing manner may be a conventional developing manner used in the art for forming a lithographic pattern, and is preferably one or more of immersion, spin immersion and spraying, for example, spin immersion.
In the method for forming a photolithographic pattern, in S4, the developing developer may be a conventional developer used in the art for forming a photolithographic pattern, such as an aqueous alkaline solution and/or an organic solvent.
The concentration of the alkaline aqueous solution may be 0.1 to 5wt%, preferably 2 to 3wt% of tetramethylammonium hydroxide (TMAH) aqueous solution.
The organic solvent is preferably one or more of 2-octanone, 2-nonanone, 2-heptanone, 3-heptanone, 4-heptanone, 2-hexanone, 3-hexanone, diisobutyl ketone, methylcyclohexanone, acetophenone, methylacetophenone, propyl acetate, butyl acetate, isobutyl acetate, pentyl acetate, isopentyl acetate, butenyl acetate, phenyl acetate, propyl formate, butyl formate, isobutyl formate, pentyl formate, isopentyl formate, methyl valerate, methyl pentenoate, methyl crotonate, ethyl crotonate, methyl lactate, ethyl lactate, propyl lactate, butyl lactate, isobutyl lactate, pentyl lactate, isoamyl lactate, methyl 2-hydroxyisobutyrate, ethyl 2-hydroxyisobutyrate, methyl benzoate, ethyl benzoate, benzyl acetate, methyl phenylacetate, benzyl formate, ethyl formate, methyl 3-phenylpropionate, benzyl propionate, ethyl phenylacetate, and 2-phenylethyl acetate.
In the method for forming a photolithographic pattern, in S4, the developing temperature may be a conventional developing temperature used in the art for forming a photolithographic pattern, preferably 10 to 30 ℃, for example, room temperature.
In the method of forming a photolithographic pattern, in S4, the developing time may be a developing time conventionally used in the art for forming a photolithographic pattern, for example, 0.1 to 3 minutes, for example, 0.5 to 2 minutes.
Any desired steps may be added to the pattern forming method. For example, after the photoresist layer is formed, a step of rinsing with pure water (post-soaking) may be introduced to extract an acid generator or the like from the film surface or wash off particles. After exposure, a rinse (after soaking) step may be introduced to remove any water remaining on the film after exposure.
The invention also provides a resin which is obtained by polymerizing the following monomers in parts by weight: 40-50 parts of monomer A, 1-7.5 parts of monomer B, 0.25-2.5 parts of monomer C and 0.25-2.5 parts of monomer D;
wherein R is 1 、R 2 、R 3 、R 4 、R 5 And R 6 The definitions of (A) and (B) are the same as those described above;
the parts and kinds of the monomer A, the parts and kinds of the monomer B, the parts and kinds of the monomer C and the parts and kinds of the monomer D are the same as those described above.
The invention also provides a preparation method of the resin, which comprises the following steps: polymerizing 40-50 parts by weight of monomer A, 1-7.5 parts by weight of monomer B, 0.25-2.5 parts by weight of monomer C and 0.25-2.5 parts by weight of monomer D in an organic solvent to obtain the resin;
R 1 、R 2 、R 3 、R 4 、R 5 and R 6 The definitions of (A) and (B) are the same as those described above;
the parts and kinds of the monomers A, the parts and kinds of the monomers B, the parts and kinds of the monomers C and the parts and kinds of the monomers D are the same as above.
The invention also provides a photoresist composition, which is prepared from the following raw materials in parts by weight: 75-95 parts of resin, 1.0-10 parts of photoacid generator, 1000-2000 parts of solvent, 0.5-3.0 parts of quencher and surfactant;
the types and parts of the resin, the parts and kinds of the photoacid generator, the parts and kinds of the solvent, the parts and kinds of the quencher and the parts and kinds of the surfactant are the same as those described above.
The invention provides a preparation method of the photoresist composition, which comprises the following steps: and (3) uniformly mixing all the components in the photoresist composition.
In the method for preparing the photoresist composition, after the mixing, a filtering step can be further included. The filtration may be performed in a manner conventional in the art, and preferably filtration using a filter is used. The filter membrane pore size of the filter is preferably 0.2 μm.
The above preferred conditions can be arbitrarily combined to obtain preferred embodiments of the present invention without departing from the common general knowledge in the art.
The reagents and starting materials used in the present invention are commercially available.
The positive progress effects of the invention are as follows: the photolithographic pattern formed by the method for forming the photolithographic pattern of the invention has at least the following advantages: excellent photosensitivity, good depth of focus (DOF) and good line width uniformity (CDU).
Detailed Description
The invention is further illustrated by the following examples, which are not intended to limit the scope of the invention. The experimental methods without specifying specific conditions in the following examples were selected according to the conventional methods and conditions, or according to the commercial instructions.
In the following examples, the operation temperature is not specifically limited, and all of the operations are carried out at room temperature. The room temperature means 10-30 ℃.
Examples 1-8 and comparative examples 1-8 resins 1-8 and comparative resins 1-8 preparation
A solution was prepared by dissolving the following monomer A, monomer B, monomer C, monomer D in the following weight parts (g) of Table 1 in 70g of Propylene Glycol Monomethyl Ether Acetate (PGMEA) under a nitrogen atmosphere. The solution was added dropwise to 30g of Propylene Glycol Monomethyl Ether Acetate (PGMEA) over 5 hours under a nitrogen atmosphere while stirring at 70 ℃. After completion of the dropwise addition, stirring was continued at 70 ℃ for 3 hours. The reaction solution was cooled to room temperature and added dropwise to 1000g of methanol. The solid thus precipitated was collected by filtration and dried under vacuum at 40 ℃ for 24 hours to obtain resins 1 to 8 and comparative resins 1 to 8 as powder solids.
TABLE 1
Numbering | Monomer A | Monomer B | Monomer C | Monomer D | Mw | Mw/Mn |
Resin 1 | 41.5 | 5 | 1.25 | 1.25 | 7100 | 1.2 |
Resin 2 | 45 | 4 | 0.5 | 0.5 | 9800 | 1.3 |
Resin 3 | 45 | 4 | 0.25 | 0.75 | 8500 | 1.2 |
Resin 4 | 45 | 2.5 | 1.25 | 1.25 | 6400 | 2 |
Resin 5 | 41.5 | 4 | 1.75 | 1.75 | 5600 | 1.9 |
Resin 6 | 47.5 | 1 | 0.75 | 0.75 | 8700 | 2 |
Resin 7 | 40 | 7.5 | 1.5 | 1 | 9300 | 1.6 |
Resin 8 | 46 | 2.5 | 0.75 | 0.75 | 8100 | 1.7 |
Comparative resin 1 | 45 | 4 | 1 | 0 | 7000 | 1.1 |
Comparative resin 2 | 47.5 | 2 | 0 | 0.5 | 9900 | 1.6 |
Comparative resin 3 | 47.5 | 0 | 1.25 | 1.25 | 8700 | 1.1 |
Comparative resin 4 | 39 | 7.5 | 2 | 1.5 | 8300 | 1.5 |
Comparative resin 5 | 39 | 7.5 | 2.5 | 1 | 6200 | 1.6 |
Comparative resin 6 | 50 | 0 | 0 | 0 | 8100 | 1.9 |
Comparative resin 7 | 49.25 | 0.25 | 0.25 | 0.25 | 8300 | 1.6 |
Comparative resin 8 | 45 | 0.5 | 2 | 2.5 | 8700 | 1.3 |
Preparation of photoresists 1-23 of examples 9-32 and comparative photoresists 1-23
The materials for photoresists 1-23 of the invention and comparative photoresists are listed in table 2.
According to the formulation shown in Table 3, solid components were added to the liquid components and stirred uniformly, and the photoresists of examples 1 to 23 and comparative examples 1 to 23 were prepared in the form of solutions by filtering through a filter having a pore size of 0.2. Mu.m.
TABLE 2
TABLE 3
Application and Effect examples ArF immersion lithography patterning test (hole Pattern test)
1. Hole pattern formation:
on a substrate (silicon wafer), a spin-on carbon film ODL-70 (carbon content: 65wt%, shin-Etsu Chemical co., ltd.) was deposited to a thickness of 200nm and a spin-on hard mask SHB-a940 (silicon content: 43 wt%; shin-Etsu Chemical co., ltd.)) containing silicon was deposited thereon to a thickness of 35 nm. Then, thereon, a photoresist composition was spin-coated, and then baked on a hot plate at 200 ℃ for 60 seconds to form a photoresist layer 100nm thick.
The resist film was exposed to varying doses through a 6% halftone phase shift mask using immersion lithography using an ArF excimer laser immersion scanner NSR-S610C (Nikon corp., NA1.30, σ 0.9/0.72, 35 ° crossed polar aperture, azimuthally polarized illumination). The photoresist layer was baked (PEB) at a temperature of 95 ℃ for 60 seconds. After PEB, the developer in table 4 was injected from the developing nozzle while the wafer was spun at 30rpm for 3 seconds, which was followed by static immersion development for 27 seconds. A hole pattern having a pitch of 100nm was formed.
2. Evaluation of photosensitivity:
the hole pattern formed above was observed under TD-SEM (CG-4000, high-Technologies Corp.). The optimum dose (Eop) is an exposure dose (mJ/cm 2) providing a hole diameter of 50nm at a pitch of 100nm, and is used as an index of photosensitivity.
3. Evaluation depth of focus (DOF) margin:
the pore size at the optimal dose was measured under TD-SEM (CG-4000) from which the DOF margin providing a size of 50nm + -5 nm was determined. Larger values indicate smaller changes in pattern size as the DOF changes and thus better DOF margins.
4. Evaluation of CDU:
the hole pattern formed above was observed under TD-SEM (CG-4000) and the diameter of 125 holes was measured. From which a triple value (3 σ) of the standard deviation (σ) was calculated and recorded as CDU. A smaller value of 3 σ indicates a smaller deviation of the pores.
5. Evaluation of PPD:
immediately after PEB (no retardation, PPD =0 h), the wafer was immersion in suspension in developer for 30 seconds to form a hole pattern having a diameter of 50nm and a pitch of 100nm. In another run, the wafer was held for 6 hours after PEB (PPD =6 h) and then developed similarly to form a pattern.
The hole patterns at PPD =0h and 6h were observed under TD-SEM (CG-4000) and the diameter of 125 holes was measured. The average thereof was taken as the pore size (CD), and the CDU was calculated by the same method as above. The difference between CD at PPD 0h and CD at PPD6h was taken as the CD shrinkage due to PPD (. DELTA.PPD CD).
The effects of photoresists P1-P23 prepared from examples 9-32 and photoresists CP1-CP23 prepared from comparative photoresists 9-23 are shown in Table 4.
The developers used in Table 4 were n-butyl acetate (D1), 2-heptanone (D2) and methyl benzoate (D3).
TABLE 4
As can be seen from the above table, the photoresist composition within the scope of the present invention shows improved DOF and CDU and reduced CD shrinkage (less CD change) due to PPD, as compared to the photoresist composition of the comparative example.
Claims (10)
1. A method of forming a lithographic pattern, comprising the steps of:
s1: coating the photoresist composition on the surface of a base material, and baking to form a photoresist layer;
s2: exposing the photoresist layer formed in the step S1;
s3: baking the photoresist layer exposed in the step S2;
s4: developing the photoresist layer baked in the step S3;
the photoresist composition is prepared from the following raw materials in parts by weight: 75-95 parts of resin, 1.0-10 parts of photoacid generator, 1000-2000 parts of solvent, 0.5-3.0 parts of quencher and surfactant;
the resin is obtained by polymerizing the following monomers in parts by weight: 40-50 parts of monomer A, 1-7.5 parts of monomer B, 0.25-2.5 parts of monomer C and 0.25-2.5 parts of monomer D;
wherein R is 1 Is C 1-10 Alkyl groups of (a);
R 2 is H or C 1-10 Alkyl groups of (a);
R 3 is C 1-10 Alkyl groups of (a);
R 4 is C 2-4 Alkenyl of (a);
R 5 and R 6 Independently is H or C 1-5 The alkyl group of (1).
2. The method of forming a lithographic pattern according to claim 1, wherein said resin satisfies one or more of the following conditions:
(1)R 1 in (b), the C 1-10 Alkyl of (A) is C 1-5 Preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl;
(2)R 2 in (b), the C 1-10 Alkyl of (A) is C 1-5 Preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl;
(3)R 3 in (b), the C 1-10 Alkyl of (A) is C 1-5 Alkyl of (3) is preferably methyl, ethyl, n-propyl, i-propylPropyl, n-butyl, sec-butyl, isobutyl, or tert-butyl;
(4)R 4 in (b), the C 2-4 Alkenyl of (A) is C 2-3 Alkenyl of (a), preferably vinyl or isopropenyl;
(5)R 5 in (b), the C 1-5 The alkyl group of (b) is preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group or a tert-butyl group.
3. The resin of claim 1, wherein the resin satisfies one or more of the following conditions:
(4) The part of the monomer A is 40 to 47.5 parts, such as 41.5 to 45 parts;
(5) The part of the monomer B is 2.5-4 parts;
(6) The portion of the monomer C is 0.25 to 1.75, such as 0.5 to 1.25;
(7) The part of the monomer D is 0.5 to 1.75 parts, for example, 0.5 to 1.25 parts;
(8) The weight average molecular weight of the resin is 5000-10000, such as 5600-9800;
(9) The resin has a molecular weight distribution coefficient of 1.0 to 2.0, for example 1.2 to 2.0.
5. The method of forming a lithographic pattern according to claim 1, wherein said resin is any one of resins 1 to 8 obtained by polymerizing the following monomers in parts by weight:
resin 1:41.5 parts of monomer A, 5 parts of monomer B, 1.25 parts of monomer C and 1.25 parts of monomer D; the weight average molecular weight is 7100, and the molecular weight distribution coefficient is 1.2;
resin 2:45 parts of monomer A, 4 parts of monomer B, 0.5 part of monomer C and 0.5 part of monomer D; the weight average molecular weight is 9800, and the molecular weight distribution coefficient is 1.3;
resin 3:45 parts of monomer A, 4 parts of monomer B, 0.25 part of monomer C and 0.75 part of monomer D; the weight average molecular weight is 8500, and the molecular weight distribution coefficient is 1.2;
resin 4:45 parts of monomer A, 2.5 parts of monomer B, 1.25 parts of monomer C and 1.25 parts of monomer D; the weight average molecular weight is 6400, and the molecular weight distribution coefficient is 2;
resin 5:41.5 parts of monomer A, 4 parts of monomer B, 1.75 parts of monomer C and 1.75 parts of monomer D; the weight average molecular weight is 5600, the molecular weight distribution coefficient is 1.9;
resin 6:47.5 parts of monomer A, 1 part of monomer B, 0.75 part of monomer C and 0.75 part of monomer D; the weight average molecular weight is 8700, and the molecular weight distribution coefficient is 2;
resin 7:40 parts of monomer A, 7.5 parts of monomer B, 1.5 parts of monomer C and 1 part of monomer D; the weight average molecular weight is 9300, the molecular weight distribution coefficient is 1.6;
resin 8:46 parts of monomer A, 2.5 parts of monomer B, 0.75 part of monomer C and 0.75 part of monomer D; the weight average molecular weight is 8100, and the molecular weight distribution coefficient is 1.7;
6. The method of forming a lithographic pattern according to claim 1, wherein said resin is prepared by: polymerizing 40-50 parts by weight of monomer A, 1-7.5 parts by weight of monomer B, 0.25-2.5 parts by weight of monomer C and 0.25-2.5 parts by weight of monomer D in an organic solvent to obtain the resin;
R 1 、R 2 、R 3 、R 4 、R 5 and R 6 Are as defined in any one of claims 1 to 5;
the part and kind of the monomer A, the part and kind of the monomer B, the part and kind of the monomer C and the part and kind of the monomer D are as defined in any one of claims 1 to 5.
7. The method of forming a lithographic pattern according to claim 6, wherein said resin satisfies one or more of the following conditions:
(1) In the polymerization reaction, the weight ratio of the total weight of the monomer a, the monomer B, the monomer C and the monomer D to the organic solvent is 0.7 to 1.2, for example 1
(2) In the polymerization reaction, the organic solvent is one or more of aromatic hydrocarbon solvents, ether solvents, methyl ethyl ketone, propylene glycol monomethyl ether acetate and gamma-butyrolactone, such as propylene glycol monomethyl ether acetate;
(3) The polymerization reaction is initiated in the presence of a free radical initiator or by means of heating; when the polymerization is initiated by heating, the polymerization temperature is preferably 50 to 150 ℃, more preferably 60 to 100 ℃, for example 70 ℃ in the polymerization.
8. The method of forming a lithographic pattern according to claim 1, wherein said photoresist composition satisfies one or more of the following conditions:
(1) In the photoresist composition, the resin is 85-95 parts, such as 90 parts;
(2) In the photoresist composition, the parts of the photoacid generator are 3-10 parts, such as 5 parts or 7 parts;
(3) In the photoresist composition, the photoacid generator is a compound having a structure represented by formula (I):
X+ Y-
(I),
(4) In the photoresist composition, the solvent is 1200-1600 parts, such as 1500 parts or 1600 parts;
(5) In the photoresist composition, the solvent is one or more of a ketone solvent, a monohydric alcohol solvent, a dihydric alcohol solvent, an ether solvent and an ester solvent, and is further preferably one or more of cyclohexanone, ethylene glycol monoethyl ether and gamma-butyrolactone;
(6) In the photoresist composition, the part of the quenching agent is 0.8-2 parts, such as 1.5 parts;
(7) In the photoresist composition, the quencher is one or more of an amine-containing compound, sulfonate and carboxylate, preferably sulfonate, and further preferably a compound of formula Q1 and/or a compound of formula Q2;
(8) In the photoresist composition, the surfactant is 0.1-0.2 part, such as 0.15 part by weight;
(9) The surfactant is one or more of FC-4430, S-381, E1004, KH-20 and KH-30, and more preferably KH-20 and/or KH-30.
9. The method of forming a lithographic pattern according to any of claims 1-8, wherein said photoresist is made from a material consisting of: said resin, said photoacid generator, said solvent, said quencher, and said surfactant;
preferably, the photoresist composition is any one prepared from the following components in parts by weight:
photoresist composition 1:85 parts of resin 1, 7 parts of a compound shown as a formula X1Y1, 1500 parts of cyclohexanone, 2 parts of a compound shown as a formula Q1 and 0.15 part of KH-30;
photoresist composition 2:75 parts of the resin 1,1 part of the compound shown in the formula X1Y1, 1000 parts of cyclohexanone, 0.5 part of the compound shown in the formula Q1 and 0.1 part of KH-30;
photoresist composition 3:80 parts of resin 1,3 parts of compound shown as a formula X1Y1, 1200 parts of cyclohexanone, 0.8 part of compound shown as a formula Q1 and 0.12 part of KH-30;
photoresist composition 4:90 parts of resin 1, 5 parts of compound shown as a formula X1Y1, 1600 parts of cyclohexanone, 1.5 parts of compound shown as a formula Q1 and 0.16 part of KH-30;
photoresist composition 5:95 parts of the resin 1, 10 parts of the compound shown in the formula X1Y1, 2000 parts of cyclohexanone, 3 parts of the compound shown in the formula Q1 and 0.2 part of KH-30;
photoresist composition 6:85 parts of resin 1, 7 parts of a compound shown as a formula X1Y3, 1500 parts of cyclohexanone, 2 parts of a compound shown as a formula Q1 and 0.15 part of KH-30;
photoresist composition 7:85 parts of resin 1, 7 parts of a compound shown as a formula X2Y5, 1500 parts of cyclohexanone, 2 parts of a compound shown as a formula Q1 and 0.15 part of KH-30;
photoresist composition 8:85 parts of resin 1, 7 parts of a compound shown as a formula X3Y6, 1500 parts of cyclohexanone, 2 parts of a compound shown as a formula Q1 and 0.15 part of KH-30;
photoresist composition 9:85 parts of resin 1, 7 parts of a compound shown as a formula X4Y4, 1500 parts of cyclohexanone, 2 parts of a compound shown as a formula Q1 and 0.15 part of KH-30;
photoresist composition 10:85 parts of resin 1, 7 parts of compound shown as a formula X5Y8, 1500 parts of cyclohexanone, 2 parts of compound shown as a formula Q1 and 0.15 part of KH-30;
photoresist composition 11:85 parts of resin 1, 7 parts of compound shown as a formula X1Y8, 1500 parts of cyclohexanone, 2 parts of compound shown as a formula Q1 and 0.15 part of KH-30;
photoresist composition 12:85 parts of resin 1, 7 parts of a compound shown as a formula X2Y7, 1500 parts of cyclohexanone, 2 parts of a compound shown as a formula Q1 and 0.15 part of KH-30;
photoresist composition 13:85 parts of the resin 1, 7 parts of the compound shown in the formula X1Y1, 1500 parts of ethylene glycol monoethyl ether, 2 parts of the compound shown in the formula Q1 and 0.15 part of KH-30;
photoresist composition 14:85 parts of resin 1, 7 parts of compound shown as a formula X1Y1, 1500 parts of gamma-butyrolactone, 2 parts of compound shown as a formula Q1 and 0.15 part of KH-30;
photoresist composition 15:85 parts of resin 1, 7 parts of compound shown as a formula X1Y1, 1500 parts of cyclohexanone, 2 parts of compound shown as a formula Q2 and 0.15 part of KH-30;
photoresist composition 16:85 parts of resin 1, 7 parts of compound shown as a formula X1Y1, 1500 parts of gamma-butyrolactone, 2 parts of compound shown as a formula Q1 and 0.15 part of KH-20;
photoresist composition 17:85 parts of resin 2, 7 parts of compound shown as formula X1Y1, 1500 parts of cyclohexanone, 2 parts of compound shown as formula Q1 and 0.15 part of KH-30;
photoresist composition 18:85 parts of resin 3, 7 parts of compound shown as formula X1Y1, 1500 parts of cyclohexanone, 2 parts of compound shown as formula Q1 and 0.15 part of KH-30;
photoresist composition 19:85 parts of resin 4, 7 parts of compound shown as formula X1Y1, 1500 parts of cyclohexanone, 2 parts of compound shown as formula Q1 and 0.15 part of KH-30;
photoresist composition 20:85 parts of resin 5, 7 parts of a compound shown as a formula X1Y1, 1500 parts of cyclohexanone, 2 parts of a compound shown as a formula Q1 and 0.15 part of KH-30;
photoresist composition 21:85 parts of resin 6, 7 parts of compound shown as a formula X1Y1, 1500 parts of cyclohexanone, 2 parts of compound shown as a formula Q1 and 0.15 part of KH-30;
photoresist composition 22:85 parts of the resin 7, 7 parts of the compound shown in the formula X1Y1, 1500 parts of cyclohexanone, 2 parts of the compound shown in the formula Q1 and 0.15 part of KH-30;
photoresist composition 23:85 parts of resin 8, 7 parts of compound shown as a formula X1Y1, 1500 parts of cyclohexanone, 2 parts of compound shown as a formula Q1 and 0.15 part of KH-30.
10. The method of forming a lithographic pattern according to claim 1, wherein said method of forming a lithographic pattern satisfies one or more of the following conditions:
(1) In S1, the coating mode is spin coating;
(2) In S1, the baking temperature is 60-200 ℃;
(3) In S1, the baking time is 1-10 minutes, such as 1 minute;
(4) In S1, the thickness of the photoresist layer is 0.05-2 μm, such as 100nm;
(5) S2, the exposure mode is high-energy radiation, electron beam exposure or immersion lithography method for providing liquid with at least 1.0 of refractive index between the projection lens and the photoresist layer to complete exposure; when the exposure mode is high-energy radiation, the exposure dose is 1-200mJ/cm 2 (ii) a For example 10-100mJ/cm 2 (ii) a When the exposure mode is electron beam exposure, the exposure dose is 0.1-100 mu C/cm 2 E.g. 0.5-50. Mu.C/cm 2 ;
(6) In S3, the baking temperature is 60-150 ℃, such as 80-140 ℃, and 95 ℃ for example;
(7) In S3, the baking time is 1-5 minutes, for example, 1 minute;
(8) In S4, the developing mode is one or more of dipping, spin immersion and spraying, for example, spin immersion;
(8) In S4, the developing agent is alkaline aqueous solution and/or organic solvent; the concentration of the alkaline aqueous solution can be 0.1-5wt%, preferably 2-3wt% of tetramethylammonium hydroxide aqueous solution;
(9) In S4, the developing temperature is 10-30 ℃, such as room temperature;
(10) In S4, the development time is 0.1 to 3 minutes, for example, 0.5 to 2 minutes.
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JPH1135522A (en) * | 1997-05-23 | 1999-02-09 | Daicel Chem Ind Ltd | Polymerizable adamantane derivative and its production |
US20050074690A1 (en) * | 2003-10-01 | 2005-04-07 | Shenggao Liu | Photoresist compositions comprising diamondoid derivatives |
US20200218154A1 (en) * | 2019-01-08 | 2020-07-09 | Shin-Etsu Chemical Co., Ltd. | Resist composition and patterning process |
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2021
- 2021-10-08 CN CN202111172205.4A patent/CN115960296A/en active Pending
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JPH1135522A (en) * | 1997-05-23 | 1999-02-09 | Daicel Chem Ind Ltd | Polymerizable adamantane derivative and its production |
US20050074690A1 (en) * | 2003-10-01 | 2005-04-07 | Shenggao Liu | Photoresist compositions comprising diamondoid derivatives |
US20200218154A1 (en) * | 2019-01-08 | 2020-07-09 | Shin-Etsu Chemical Co., Ltd. | Resist composition and patterning process |
Non-Patent Citations (1)
Title |
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