JP2009276363A - レジスト材料及びパターン形成方法 - Google Patents
レジスト材料及びパターン形成方法 Download PDFInfo
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- JP2009276363A JP2009276363A JP2008124476A JP2008124476A JP2009276363A JP 2009276363 A JP2009276363 A JP 2009276363A JP 2008124476 A JP2008124476 A JP 2008124476A JP 2008124476 A JP2008124476 A JP 2008124476A JP 2009276363 A JP2009276363 A JP 2009276363A
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- hydrogen atom
- sulfonate
- carbon atoms
- acid
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- 239000000463 material Substances 0.000 title claims abstract description 94
- 238000000034 method Methods 0.000 title claims abstract description 41
- 150000001875 compounds Chemical class 0.000 claims abstract description 108
- 229920000642 polymer Polymers 0.000 claims abstract description 97
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 91
- 125000004432 carbon atom Chemical group C* 0.000 claims description 124
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 83
- 239000002253 acid Substances 0.000 claims description 64
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 59
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 47
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
- 230000001681 protective effect Effects 0.000 claims description 31
- 229910052799 carbon Inorganic materials 0.000 claims description 26
- 229920002120 photoresistant polymer Polymers 0.000 claims description 24
- 239000000758 substrate Substances 0.000 claims description 19
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 19
- 239000003513 alkali Substances 0.000 claims description 17
- 239000003960 organic solvent Substances 0.000 claims description 17
- 150000001721 carbon Chemical group 0.000 claims description 16
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 13
- 238000004090 dissolution Methods 0.000 claims description 11
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
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- 238000010894 electron beam technology Methods 0.000 claims description 6
- 125000000686 lactone group Chemical group 0.000 claims description 5
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- 0 CCC(C(*1)C1C1C2)C2CC1(*)C(OC(CC1(*)OC*1)C1CCCC1)=O Chemical compound CCC(C(*1)C1C1C2)C2CC1(*)C(OC(CC1(*)OC*1)C1CCCC1)=O 0.000 description 21
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- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 18
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 13
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- 125000004430 oxygen atom Chemical group O* 0.000 description 12
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- 238000000671 immersion lithography Methods 0.000 description 11
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- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 10
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 10
- 125000000524 functional group Chemical group 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
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- 230000000052 comparative effect Effects 0.000 description 9
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- 150000003949 imides Chemical class 0.000 description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 8
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
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- 125000004093 cyano group Chemical group *C#N 0.000 description 8
- 125000004185 ester group Chemical group 0.000 description 8
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 8
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
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- 238000003756 stirring Methods 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 8
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 8
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 7
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 150000002596 lactones Chemical group 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- NCJZVRPXSSYDBG-UHFFFAOYSA-N 2,2,2-trifluoro-1-(4-methoxyphenyl)ethanone Chemical compound COC1=CC=C(C(=O)C(F)(F)F)C=C1 NCJZVRPXSSYDBG-UHFFFAOYSA-N 0.000 description 6
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000001459 lithography Methods 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 description 6
- 125000003518 norbornenyl group Chemical class C12(C=CC(CC1)C2)* 0.000 description 6
- 125000005188 oxoalkyl group Chemical group 0.000 description 6
- YFSUTJLHUFNCNZ-UHFFFAOYSA-N perfluorooctane-1-sulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YFSUTJLHUFNCNZ-UHFFFAOYSA-N 0.000 description 6
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- 125000004665 trialkylsilyl group Chemical group 0.000 description 6
- GKNWQHIXXANPTN-UHFFFAOYSA-M 1,1,2,2,2-pentafluoroethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)(F)F GKNWQHIXXANPTN-UHFFFAOYSA-M 0.000 description 5
- JGTNAGYHADQMCM-UHFFFAOYSA-M 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JGTNAGYHADQMCM-UHFFFAOYSA-M 0.000 description 5
- GGNTZQPZZSOHAN-UHFFFAOYSA-N 1,1,3,3,3-pentafluoro-2-(4-methylphenyl)sulfonyloxypropane-1-sulfonic acid Chemical compound CC1=CC=C(S(=O)(=O)OC(C(F)(F)F)C(F)(F)S(O)(=O)=O)C=C1 GGNTZQPZZSOHAN-UHFFFAOYSA-N 0.000 description 5
- RSERVFRSDPESLG-UHFFFAOYSA-N 1,1,3,3,3-pentafluoro-2-(naphthalene-2-carbonyloxy)propane-1-sulfonic acid Chemical compound C1=CC=CC2=CC(C(=O)OC(C(F)(F)S(=O)(=O)O)C(F)(F)F)=CC=C21 RSERVFRSDPESLG-UHFFFAOYSA-N 0.000 description 5
- ZSXYJNYYDJTZPB-UHFFFAOYSA-N 1-(1,1-difluoro-2h-naphthalen-2-yl)ethanesulfonic acid Chemical compound C1=CC=C2C(F)(F)C(C(C)S(O)(=O)=O)C=CC2=C1 ZSXYJNYYDJTZPB-UHFFFAOYSA-N 0.000 description 5
- KYXIHKXHBSORRJ-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)-2,2,2-trifluoroethanone Chemical compound CC1=CC=C(C(=O)C(F)(F)F)C(C)=C1 KYXIHKXHBSORRJ-UHFFFAOYSA-N 0.000 description 5
- VINRTVDNUHIWCB-UHFFFAOYSA-N 2,2,2-trifluoro-1-(2,4,6-trimethylphenyl)ethanone Chemical compound CC1=CC(C)=C(C(=O)C(F)(F)F)C(C)=C1 VINRTVDNUHIWCB-UHFFFAOYSA-N 0.000 description 5
- DYILUJUELMWXAL-UHFFFAOYSA-N 2,2,2-trifluoro-1-(4-methylphenyl)ethanone Chemical compound CC1=CC=C(C(=O)C(F)(F)F)C=C1 DYILUJUELMWXAL-UHFFFAOYSA-N 0.000 description 5
- XGMDYIYCKWMWLY-UHFFFAOYSA-N 2,2,2-trifluoroethanesulfonic acid Chemical compound OS(=O)(=O)CC(F)(F)F XGMDYIYCKWMWLY-UHFFFAOYSA-N 0.000 description 5
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- JHQDBQYFKARISA-UHFFFAOYSA-N 2,2,2-trifluoro-1-(2-methylphenyl)ethanone Chemical compound CC1=CC=CC=C1C(=O)C(F)(F)F JHQDBQYFKARISA-UHFFFAOYSA-N 0.000 description 3
- YHGKEORTCHVBQH-UHFFFAOYSA-M 2,4,6-tri(propan-2-yl)benzenesulfonate Chemical compound CC(C)C1=CC(C(C)C)=C(S([O-])(=O)=O)C(C(C)C)=C1 YHGKEORTCHVBQH-UHFFFAOYSA-M 0.000 description 3
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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- WYPIYJCVKPAZOQ-UHFFFAOYSA-N methyl 3-[bis(2-acetyloxyethyl)amino]propanoate Chemical compound COC(=O)CCN(CCOC(C)=O)CCOC(C)=O WYPIYJCVKPAZOQ-UHFFFAOYSA-N 0.000 description 1
- PDLCQBOPNILNFH-UHFFFAOYSA-N methyl 3-[bis(2-hydroxyethyl)amino]propanoate Chemical compound COC(=O)CCN(CCO)CCO PDLCQBOPNILNFH-UHFFFAOYSA-N 0.000 description 1
- BHTBQFHOJIBPKY-UHFFFAOYSA-N methyl 3-[bis(2-methoxyethyl)amino]propanoate Chemical compound COCCN(CCOC)CCC(=O)OC BHTBQFHOJIBPKY-UHFFFAOYSA-N 0.000 description 1
- YDNHCHDMPIHHGH-UHFFFAOYSA-N methyl 3-[bis(3-methoxy-3-oxopropyl)amino]propanoate Chemical compound COC(=O)CCN(CCC(=O)OC)CCC(=O)OC YDNHCHDMPIHHGH-UHFFFAOYSA-N 0.000 description 1
- BKQUFNJLMGRJHL-UHFFFAOYSA-N methyl 3-[cyanomethyl(2-hydroxyethyl)amino]propanoate Chemical compound COC(=O)CCN(CCO)CC#N BKQUFNJLMGRJHL-UHFFFAOYSA-N 0.000 description 1
- ZCOLLGOATUZZNL-UHFFFAOYSA-N methyl 3-[cyanomethyl(2-methoxyethyl)amino]propanoate Chemical compound COCCN(CC#N)CCC(=O)OC ZCOLLGOATUZZNL-UHFFFAOYSA-N 0.000 description 1
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
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- JHYKOXJKJHTKTE-UHFFFAOYSA-N methyl 3-pyrrolidin-1-ylpropanoate Chemical compound COC(=O)CCN1CCCC1 JHYKOXJKJHTKTE-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
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- BNUHBJSGYGOLSN-UHFFFAOYSA-N n'-[2-[2-[2-(dimethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound CN(C)CCNCCNCCNCCN BNUHBJSGYGOLSN-UHFFFAOYSA-N 0.000 description 1
- VGIVLIHKENZQHQ-UHFFFAOYSA-N n,n,n',n'-tetramethylmethanediamine Chemical compound CN(C)CN(C)C VGIVLIHKENZQHQ-UHFFFAOYSA-N 0.000 description 1
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- ZQJAONQEOXOVNR-UHFFFAOYSA-N n,n-di(nonyl)nonan-1-amine Chemical compound CCCCCCCCCN(CCCCCCCCC)CCCCCCCCC ZQJAONQEOXOVNR-UHFFFAOYSA-N 0.000 description 1
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- CLZGJKHEVKJLLS-UHFFFAOYSA-N n,n-diheptylheptan-1-amine Chemical compound CCCCCCCN(CCCCCCC)CCCCCCC CLZGJKHEVKJLLS-UHFFFAOYSA-N 0.000 description 1
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- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 1
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- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
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- VRAWXSCCKYEDOG-UHFFFAOYSA-N tribenzylsulfanium Chemical compound C=1C=CC=CC=1C[S+](CC=1C=CC=CC=1)CC1=CC=CC=C1 VRAWXSCCKYEDOG-UHFFFAOYSA-N 0.000 description 1
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- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- USMVHTQGEMDHKL-UHFFFAOYSA-M triphenylsulfanium;2,4,6-tri(propan-2-yl)benzenesulfonate Chemical compound CC(C)C1=CC(C(C)C)=C(S([O-])(=O)=O)C(C(C)C)=C1.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 USMVHTQGEMDHKL-UHFFFAOYSA-M 0.000 description 1
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- QKFJVDSYTSWPII-UHFFFAOYSA-N tris(4-methylphenyl)sulfanium Chemical compound C1=CC(C)=CC=C1[S+](C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 QKFJVDSYTSWPII-UHFFFAOYSA-N 0.000 description 1
- DMJFWVWYOPMJIK-UHFFFAOYSA-N tris[3,4-bis[(2-methylpropan-2-yl)oxy]phenyl]sulfanium Chemical compound C1=C(OC(C)(C)C)C(OC(C)(C)C)=CC=C1[S+](C=1C=C(OC(C)(C)C)C(OC(C)(C)C)=CC=1)C1=CC=C(OC(C)(C)C)C(OC(C)(C)C)=C1 DMJFWVWYOPMJIK-UHFFFAOYSA-N 0.000 description 1
- HENPLGIMUIZOJQ-UHFFFAOYSA-N tris[3-[(2-methylpropan-2-yl)oxy]phenyl]sulfanium Chemical compound CC(C)(C)OC1=CC=CC([S+](C=2C=C(OC(C)(C)C)C=CC=2)C=2C=C(OC(C)(C)C)C=CC=2)=C1 HENPLGIMUIZOJQ-UHFFFAOYSA-N 0.000 description 1
- PNXQORBBJALXKA-UHFFFAOYSA-N tris[4-[(2-methylpropan-2-yl)oxy]phenyl]sulfanium Chemical compound C1=CC(OC(C)(C)C)=CC=C1[S+](C=1C=CC(OC(C)(C)C)=CC=1)C1=CC=C(OC(C)(C)C)C=C1 PNXQORBBJALXKA-UHFFFAOYSA-N 0.000 description 1
- JXPBRQHHMIKAPW-UHFFFAOYSA-N tris[4-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethoxy]phenyl]sulfanium Chemical compound C1=CC(OCC(=O)OC(C)(C)C)=CC=C1[S+](C=1C=CC(OCC(=O)OC(C)(C)C)=CC=1)C1=CC=C(OCC(=O)OC(C)(C)C)C=C1 JXPBRQHHMIKAPW-UHFFFAOYSA-N 0.000 description 1
Classifications
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0046—Photosensitive materials with perfluoro compounds, e.g. for dry lithography
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
- G03F7/0395—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition the macromolecular compound having a backbone with alicyclic moieties
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
- G03F7/0397—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition the macromolecular compound having an alicyclic moiety in a side chain
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/20—Exposure; Apparatus therefor
- G03F7/2041—Exposure; Apparatus therefor in the presence of a fluid, e.g. immersion; using fluid cooling means
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/106—Binder containing
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
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- Y10S430/106—Binder containing
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Abstract
Description
請求項1:
(A)下記一般式(1a)及び(2a)で表される繰り返し単位を必須単位として構成される高分子化合物(P1)、(B)ラクトン環と水酸基のいずれか一方又は双方を有する骨格及び/又は無水マレイン酸由来の骨格を有し、酸の作用によりアルカリ現像液に可溶となる高分子化合物、(C)高エネルギー線の露光により酸を発生する化合物、(D)有機溶剤を含有することを特徴とするレジスト材料。
請求項2:
(A)下記一般式(1a)、(1b)及び(2a)で表される繰り返し単位を必須単位として構成される高分子化合物(P1’)、(B)ラクトン環と水酸基のいずれか一方又は双方を有する骨格及び/又は無水マレイン酸由来の骨格を有し、酸の作用によりアルカリ現像液に可溶となる高分子化合物、(C)高エネルギー線の露光により酸を発生する化合物、(D)有機溶剤を含有することを特徴とするレジスト材料。
請求項3:
(A)下記一般式(1a)、(1b)、(2a)及び(2b)で表される繰り返し単位を必須単位として構成される高分子化合物(P1’’)、(B)ラクトン環と水酸基のいずれか一方又は双方を有する骨格及び/又は無水マレイン酸由来の骨格を有し、酸の作用によりアルカリ現像液に可溶となる高分子化合物、(C)高エネルギー線の露光により酸を発生する化合物、(D)有機溶剤を含有することを特徴とするレジスト材料。
請求項4:
(A)下記一般式(1a)及び(2a’)で表される繰り返し単位を必須単位として構成される高分子化合物(P1−H)の式(1a)の水酸基及び式(2a’)の水酸基のうち、水酸基の一部又は全部を保護基で保護した高分子化合物(P2)、(B)ラクトン環と水酸基のいずれか一方又は双方を有する骨格及び/又は無水マレイン酸由来の骨格を有し、酸の作用によりアルカリ現像液に可溶となる高分子化合物、(C)高エネルギー線の露光により酸を発生する化合物、(D)有機溶剤を含有することを特徴とするレジスト材料。
請求項5:
更に、(E)塩基性化合物を含有することを特徴とする請求項1乃至4のいずれか1項に記載のレジスト材料。
請求項6:
更に、(F)溶解阻止剤を含有することを特徴とする請求項1乃至5のいずれか1項に記載のレジスト材料。
請求項7:
(1)請求項1乃至6のいずれか1項に記載のレジスト材料を基板上に塗布する工程と、(2)加熱処理後、フォトマスクを介して高エネルギー線で露光する工程と、(3)現像液を用いて現像する工程とを含むことを特徴とするパターン形成方法。
請求項8:
(1)請求項1乃至6のいずれか1項に記載のレジスト材料を基板上に塗布する工程と、(2)加熱処理後、投影レンズとウエハーの間に液体を挿入させ、フォトマスクを介して高エネルギー線で露光する工程と、(3)現像液を用いて現像する工程とを含むことを特徴とするパターン形成方法。
請求項9:
(1)請求項1乃至6のいずれか1項に記載のレジスト材料を基板上に塗布する工程と、(2)フォトレジスト膜の上に保護膜層を形成する工程と、(3)加熱処理後、投影レンズとウエハーの間に液体を挿入させ、フォトマスクを介して高エネルギー線で露光する工程と、(4)現像液を用いて現像する工程とを含むことを特徴とするパターン形成方法。
請求項10:
前記露光工程において、投影レンズと基板の間に挿入する液体が水であることを特徴とする請求項8又は9に記載のパターン形成方法。
請求項11:
露光光源として波長180〜250nmの範囲の高エネルギー線を用いることを特徴とする請求項7乃至10に記載のパターン形成方法。
請求項12:
(1)請求項1乃至6のいずれか1項に記載のレジスト材料をマスクブランクス上に塗布する工程と、(2)加熱処理後、真空中電子ビームで露光する工程と、(3)現像液を用いて現像する工程とを含むことを特徴とするパターン形成方法。
また、式(L1)において、RL01、RL02は水素原子又は炭素数1〜18、好ましくは1〜10の直鎖状、分岐状又は環状のアルキル基を示し、具体的にはメチル基、エチル基、プロピル基、イソプロピル基、n−ブチル基、sec−ブチル基、tert−ブチル基、シクロペンチル基、シクロヘキシル基、2−エチルヘキシル基、n−オクチル基、アダマンチル基等が例示できる。RL03は炭素数1〜18、好ましくは炭素数1〜10の酸素原子等のヘテロ原子を有してもよい一価の炭化水素基を示し、直鎖状、分岐状又は環状のアルキル基、これらの水素原子の一部が水酸基、アルコキシ基、オキソ基、アミノ基、アルキルアミノ基等に置換されたものを挙げることができ、具体的には、直鎖状、分岐状又は環状のアルキル基としては上記RL01、RL02と同様のものが例示でき、置換アルキル基としては下記の基等が例示できる。
上記一般式(1a)の単位に対応するモノマーの総モル数をU1、
上記一般式(1b)の単位に対応するモノマーの総モル数をU2、
上記一般式(2a)の単位に対応するモノマーの総モル数をU3、
上記一般式(2b)の単位に対応するモノマーの総モル数をU4、
U1+U2+U3+U4=UA
とした場合、
0<U1/UA<1、より好ましくは0.2≦U1/UA≦0.7、更に好ましくは0.3≦U1/UA≦0.7、
0≦U2/UA<1、より好ましくは0.1≦U2/UA≦0.7、更に好ましくは0.1≦U2/UA≦0.5、
0≦U3/UA<1、より好ましくは0.1≦U3/UA≦0.6、更に好ましくは0.1≦U3/UA≦0.5、
0≦U4/UA<1、より好ましくは0≦U4/UA≦0.7、更に好ましくは0.1≦U4/UA≦0.5
である。
また、レジスト材料の疎水性添加物としての性能向上のため、上記一般式(7a)〜(7e)、(8a)〜(8e)、(9a)〜(9c)、(10a)〜(10c)で表される繰り返し単位を樹脂中に組み込む場合、それらの単位に対応するモノマーの総モル数をU5とし、
U1+U2+U3+U4+U5=UA’とすると、
0<UA/UA’≦1、より好ましくは0.6≦UA/UA’≦1、更に好ましくは0.8≦UA/UA’≦1
である。
イミド類としては、フタルイミド、サクシンイミド、マレイミド等が例示される。
カーバメート類としては、N−t−ブトキシカルボニル−N,N−ジシクロヘキシルアミン、N−t−ブトキシカルボニルベンズイミダゾール、オキサゾリジノン等が例示される。
N(X)n(Y)3-n (B)−1
下記一般式(A1)〜(A10)で示される化合物のうち、フェノール性水酸基の水素原子の一部又は全部を−R401−COOH(R401は炭素数1〜10の直鎖状又は分岐状のアルキレン基)により置換してなり、かつ分子中のフェノール性水酸基(C)と≡C−COOHで示される基(D)とのモル比率がC/(C+D)=0.1〜1.0である化合物。
[II群]
下記一般式(A11)〜(A15)で示される化合物。
窒素雰囲気下のフラスコに45.94gのMonomer1、19.30gのMonomer2、35.55gのMonomer6、42.9gのγ−ブチロラクトンを投入して、溶液温度を20〜25℃とした。撹拌しながら60℃まで加熱して4.51gの2,2’−アゾビス(イソ酪酸)ジメチルを投入し、重合液の温度を60℃に保ったまま24時間撹拌を続け、熟成終了後に室温まで冷却した。得られた重合液にジイソプロピルエーテル300gと超純水300gを投入し、15分撹拌した。水層を廃棄後、有機層を水300gで3回洗浄した。有機層を濃縮後、1,500gのヘキサン中に滴下し、析出した共重合体を分離後、600gのヘキサンで2回洗浄し、白色固体を分離した。白色固体を50℃で24時間真空乾燥させることにより目的の高分子化合物(Polymer1)53.6gを得た。樹脂の組成を1H−NMRで分析した結果、共重合体中のMonomer1、Monomer2、Monomer6の組成比は53/29/18モル%であった。また、得られた共重合体のGPC測定を行った結果、重量平均分子量(Mw)はポリスチレン換算で7,100、分散度(Mw/Mn)は1.4であった。
Polymer1の合成と同様の処方を用いて表1に示すPolymer2〜6の合成を行い、GPC測定を行った。結果は表1に示す通りであった。
窒素雰囲気下のフラスコに73.28gのMonomer1、30.42gのMonomer6、42.9gのγ−ブチロラクトンを投入して、溶液温度を20〜25℃とした。撹拌しながら60℃まで加熱して3.47gの2,2’−アゾビス(イソ酪酸)ジメチルを投入し、重合液の温度を60℃に保ったまま24時間撹拌を続け、熟成終了後に室温まで冷却した。得られた重合液にジイソプロピルエーテル300gと超純水300gを投入し、15分撹拌した。水層を廃棄後、有機層を水300gで3回洗浄した。有機層を濃縮後、1,500gのヘキサン中に滴下し、析出した共重合体を分離後、600gのヘキサンで2回洗浄し、白色固体を分離した。白色固体を50℃で24時間真空乾燥させることにより目的の高分子化合物(Polymer7’)50.6gを得た。樹脂の組成を1H−NMRで分析した結果、共重合体中のMonomer1とMonomer6の組成比は72/28モル%であった。また、得られた共重合体のGPC測定を行った結果、重量平均分子量(Mw)はポリスチレン換算で9,000、分散度(Mw/Mn)は1.4であった。
次に、窒素雰囲気下で得られたPolymer7’のうち50gをテトラヒドロフラン200gに溶解し、氷浴下でトリエチルアミン4.6g、1−クロロ−1−メトキシ−2−メチル−プロパン4.6gを添加し、室温で10時間撹拌を続けた。フラスコ内にジイソプロピルエーテル100gと水150gを添加して撹拌後、水層を分離し、有機層を濃縮した。濃縮液を750gのヘキサン中に滴下し、析出した共重合体を分離後、300gのヘキサンで2回洗浄し、白色固体を分離した。白色固体を50℃で24時間真空乾燥させることにより目的の高分子化合物(Polymer7)44.1gを得た。水酸基の保護化率を1H−NMRで分析した結果、水酸基全体の28%が1−メトキシ−2−メチル−プロピル基で置換されていることがわかった。また、得られた共重合体のGPC測定を行った結果、重量平均分子量(Mw)はポリスチレン換算で9,200、分散度(Mw/Mn)は1.4であった。
窒素雰囲気下のフラスコに100.0gのMonomer9、3.91gの2,2’−アゾビス(イソ酪酸)ジメチル、100.0gのイソプロピルアルコールを投入して単量体溶液を調製し、溶液温度を20〜25℃とした。窒素雰囲気下の別のフラスコに50.0gのイソプロピルアルコールを投入し、撹拌しながら80℃まで加熱した後、上記単量体溶液を4時間かけて滴下した。滴下終了後、重合液の温度を80℃に保ったまま3時間撹拌を続け、熟成終了後に室温まで冷却した。得られた重合液を2,000gの水中に滴下し、析出した共重合体を濾別した。得られた共重合体を600gのヘキサン/イソプロピルエーテル(9/1)混合溶液で4回洗浄し、白色固体を分離した。白色固体を50℃で20時間真空乾燥させることにより目的の高分子化合物(比較Polymer1)92.8gを得た。得られた共重合体のGPC測定を行った結果、重量平均分子量(Mw)はポリスチレン換算で7,800、分散度(Mw/Mn)は1.6であった。
比較ポリマー合成例1と同様の処方で、Monomer10のホモポリマーを合成した(比較Polymer2)。ポリマーのGPC測定を行った結果、重量平均分子量(Mw)はポリスチレン換算で7,900、分散度(Mw/Mn)は1.6であった。
下記Resist Polymerを5g、上記Polymer1〜7、比較Polymer1及び2を0.5g、PAG1を0.25g、Quencher1を0.05g用い、これらを75gのプロピレングリコールモノエチルエーテルアセテート(PGMEA)に溶解させ、0.2μmサイズのポリプロピレンフィルターで濾過し、レジスト溶液を作製した。また、比較例として、上記Polymer1〜7、比較Polymer1及び2を添加しないレジスト溶液も調製した。
表2において転落角が低いほどレジスト上の水は流動し易く、後退接触角が高いほど高速のスキャン露光でも液滴が残りにくい。本発明の高分子化合物を配合したレジスト溶液から形成されたフォトレジスト膜は、配合しないフォトレジスト膜と比較して後退接触角を飛躍的に向上させることができ、かつ転落角は悪化させないことが確認できた。
表2から明らかなように、本発明による高分子化合物を配合したレジスト溶液から形成されたフォトレジスト膜では、フォトレジスト膜から水への光酸発生剤成分の溶出を抑制する効果が認められた。
表2の結果から、露光後に純水リンスを行った場合、本発明の高分子化合物を配合しないレジスト溶液ではパターン形状がT−トップ形状になった。これに対し、本発明の高分子化合物を配合したレジスト溶液を使った場合は矩形形状になることがわかった。
Claims (12)
- (A)下記一般式(1a)及び(2a)で表される繰り返し単位を必須単位として構成される高分子化合物(P1)、(B)ラクトン環と水酸基のいずれか一方又は双方を有する骨格及び/又は無水マレイン酸由来の骨格を有し、酸の作用によりアルカリ現像液に可溶となる高分子化合物、(C)高エネルギー線の露光により酸を発生する化合物、(D)有機溶剤を含有することを特徴とするレジスト材料。
- (A)下記一般式(1a)、(1b)及び(2a)で表される繰り返し単位を必須単位として構成される高分子化合物(P1’)、(B)ラクトン環と水酸基のいずれか一方又は双方を有する骨格及び/又は無水マレイン酸由来の骨格を有し、酸の作用によりアルカリ現像液に可溶となる高分子化合物、(C)高エネルギー線の露光により酸を発生する化合物、(D)有機溶剤を含有することを特徴とするレジスト材料。
- (A)下記一般式(1a)、(1b)、(2a)及び(2b)で表される繰り返し単位を必須単位として構成される高分子化合物(P1’’)、(B)ラクトン環と水酸基のいずれか一方又は双方を有する骨格及び/又は無水マレイン酸由来の骨格を有し、酸の作用によりアルカリ現像液に可溶となる高分子化合物、(C)高エネルギー線の露光により酸を発生する化合物、(D)有機溶剤を含有することを特徴とするレジスト材料。
- (A)下記一般式(1a)及び(2a’)で表される繰り返し単位を必須単位として構成される高分子化合物(P1−H)の式(1a)の水酸基及び式(2a’)の水酸基のうち、水酸基の一部又は全部を保護基で保護した高分子化合物(P2)、(B)ラクトン環と水酸基のいずれか一方又は双方を有する骨格及び/又は無水マレイン酸由来の骨格を有し、酸の作用によりアルカリ現像液に可溶となる高分子化合物、(C)高エネルギー線の露光により酸を発生する化合物、(D)有機溶剤を含有することを特徴とするレジスト材料。
- 更に、(E)塩基性化合物を含有することを特徴とする請求項1乃至4のいずれか1項に記載のレジスト材料。
- 更に、(F)溶解阻止剤を含有することを特徴とする請求項1乃至5のいずれか1項に記載のレジスト材料。
- (1)請求項1乃至6のいずれか1項に記載のレジスト材料を基板上に塗布する工程と、(2)加熱処理後、フォトマスクを介して高エネルギー線で露光する工程と、(3)現像液を用いて現像する工程とを含むことを特徴とするパターン形成方法。
- (1)請求項1乃至6のいずれか1項に記載のレジスト材料を基板上に塗布する工程と、(2)加熱処理後、投影レンズとウエハーの間に液体を挿入させ、フォトマスクを介して高エネルギー線で露光する工程と、(3)現像液を用いて現像する工程とを含むことを特徴とするパターン形成方法。
- (1)請求項1乃至6のいずれか1項に記載のレジスト材料を基板上に塗布する工程と、(2)フォトレジスト膜の上に保護膜層を形成する工程と、(3)加熱処理後、投影レンズとウエハーの間に液体を挿入させ、フォトマスクを介して高エネルギー線で露光する工程と、(4)現像液を用いて現像する工程とを含むことを特徴とするパターン形成方法。
- 前記露光工程において、投影レンズと基板の間に挿入する液体が水であることを特徴とする請求項8又は9に記載のパターン形成方法。
- 露光光源として波長180〜250nmの範囲の高エネルギー線を用いることを特徴とする請求項7乃至10に記載のパターン形成方法。
- (1)請求項1乃至6のいずれか1項に記載のレジスト材料をマスクブランクス上に塗布する工程と、(2)加熱処理後、真空中電子ビームで露光する工程と、(3)現像液を用いて現像する工程とを含むことを特徴とするパターン形成方法。
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KR101329938B1 (ko) | 2013-11-14 |
US8101335B2 (en) | 2012-01-24 |
US20090280434A1 (en) | 2009-11-12 |
TW201009494A (en) | 2010-03-01 |
TWI417654B (zh) | 2013-12-01 |
KR20090117995A (ko) | 2009-11-17 |
JP4650644B2 (ja) | 2011-03-16 |
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