WO2015146524A1 - パターン形成方法 - Google Patents
パターン形成方法 Download PDFInfo
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- WO2015146524A1 WO2015146524A1 PCT/JP2015/056437 JP2015056437W WO2015146524A1 WO 2015146524 A1 WO2015146524 A1 WO 2015146524A1 JP 2015056437 W JP2015056437 W JP 2015056437W WO 2015146524 A1 WO2015146524 A1 WO 2015146524A1
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- Prior art keywords
- silicon
- containing film
- group
- film
- pattern
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 55
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 108
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 107
- 239000010703 silicon Substances 0.000 claims abstract description 107
- 239000000203 mixture Substances 0.000 claims abstract description 47
- 239000000758 substrate Substances 0.000 claims abstract description 40
- 239000007864 aqueous solution Substances 0.000 claims abstract description 29
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 29
- 239000007788 liquid Substances 0.000 claims abstract description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- 150000002222 fluorine compounds Chemical class 0.000 claims abstract description 9
- 125000005843 halogen group Chemical group 0.000 claims abstract description 8
- 239000002253 acid Substances 0.000 claims abstract description 7
- 125000000962 organic group Chemical group 0.000 claims abstract description 5
- 239000007859 condensation product Substances 0.000 claims abstract description 3
- 150000003377 silicon compounds Chemical class 0.000 claims abstract description 3
- -1 silane compound Chemical class 0.000 claims description 50
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 38
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- 229910001868 water Inorganic materials 0.000 claims description 26
- 229910021529 ammonia Inorganic materials 0.000 claims description 17
- 238000005530 etching Methods 0.000 claims description 15
- 229910000077 silane Inorganic materials 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 239000003960 organic solvent Substances 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 238000002156 mixing Methods 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 125000004018 acid anhydride group Chemical group 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 239000012528 membrane Substances 0.000 claims description 6
- 230000007261 regionalization Effects 0.000 claims description 5
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 3
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 claims 1
- 239000000243 solution Substances 0.000 description 37
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 24
- 239000002904 solvent Substances 0.000 description 24
- 238000003786 synthesis reaction Methods 0.000 description 23
- 229920001296 polysiloxane Polymers 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000007787 solid Substances 0.000 description 13
- 239000011347 resin Substances 0.000 description 12
- 229920005989 resin Polymers 0.000 description 12
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000007654 immersion Methods 0.000 description 9
- 239000011248 coating agent Substances 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 235000006408 oxalic acid Nutrition 0.000 description 8
- 230000002378 acidificating effect Effects 0.000 description 7
- 238000004132 cross linking Methods 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 150000004756 silanes Chemical class 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 238000001312 dry etching Methods 0.000 description 6
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 6
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 6
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000004210 ether based solvent Substances 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 5
- 239000011259 mixed solution Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 4
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 230000003301 hydrolyzing effect Effects 0.000 description 3
- 239000005453 ketone based solvent Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 229910017464 nitrogen compound Inorganic materials 0.000 description 3
- 150000002830 nitrogen compounds Chemical group 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- APFRUMUZEFOCFO-UHFFFAOYSA-N 1-methoxybutan-1-ol Chemical compound CCCC(O)OC APFRUMUZEFOCFO-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
- MKZHZHRXBKRYRP-UHFFFAOYSA-N 3-propyl-3-triethoxysilyloxolane-2,5-dione Chemical compound CCO[Si](OCC)(OCC)C1(CCC)CC(=O)OC1=O MKZHZHRXBKRYRP-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-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
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 235000002597 Solanum melongena Nutrition 0.000 description 2
- 244000061458 Solanum melongena Species 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 238000005229 chemical vapour deposition Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 239000003759 ester based solvent Substances 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010304 firing Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 2
- 229920005591 polysilicon Polymers 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- XGQJGMGAMHFMAO-UHFFFAOYSA-N 1,3,4,6-tetrakis(methoxymethyl)-3a,6a-dihydroimidazo[4,5-d]imidazole-2,5-dione Chemical compound COCN1C(=O)N(COC)C2C1N(COC)C(=O)N2COC XGQJGMGAMHFMAO-UHFFFAOYSA-N 0.000 description 1
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- WCIWKVYUSWPZEF-UHFFFAOYSA-N 1-[dimethoxy(phenyl)silyl]oxy-n,n-dimethylmethanamine Chemical compound CN(C)CO[Si](OC)(OC)C1=CC=CC=C1 WCIWKVYUSWPZEF-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- UJEGHEMJVNQWOJ-UHFFFAOYSA-N 1-heptoxyheptane Chemical compound CCCCCCCOCCCCCCC UJEGHEMJVNQWOJ-UHFFFAOYSA-N 0.000 description 1
- BPIUIOXAFBGMNB-UHFFFAOYSA-N 1-hexoxyhexane Chemical compound CCCCCCOCCCCCC BPIUIOXAFBGMNB-UHFFFAOYSA-N 0.000 description 1
- AOPDRZXCEAKHHW-UHFFFAOYSA-N 1-pentoxypentane Chemical compound CCCCCOCCCCC AOPDRZXCEAKHHW-UHFFFAOYSA-N 0.000 description 1
- MHHJQVRGRPHIMR-UHFFFAOYSA-N 1-phenylprop-2-en-1-ol Chemical compound C=CC(O)C1=CC=CC=C1 MHHJQVRGRPHIMR-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 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
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 1
- KXYAVSFOJVUIHT-UHFFFAOYSA-N 2-vinylnaphthalene Chemical compound C1=CC=CC2=CC(C=C)=CC=C21 KXYAVSFOJVUIHT-UHFFFAOYSA-N 0.000 description 1
- PKNKULBDCRZSBT-UHFFFAOYSA-N 3,4,5-trimethylnonan-2-one Chemical compound CCCCC(C)C(C)C(C)C(C)=O PKNKULBDCRZSBT-UHFFFAOYSA-N 0.000 description 1
- GXDMUOPCQNLBCZ-UHFFFAOYSA-N 3-(3-triethoxysilylpropyl)oxolane-2,5-dione Chemical compound CCO[Si](OCC)(OCC)CCCC1CC(=O)OC1=O GXDMUOPCQNLBCZ-UHFFFAOYSA-N 0.000 description 1
- IWTYTFSSTWXZFU-UHFFFAOYSA-N 3-chloroprop-1-enylbenzene Chemical compound ClCC=CC1=CC=CC=C1 IWTYTFSSTWXZFU-UHFFFAOYSA-N 0.000 description 1
- AMZXVEFLFBLDEM-UHFFFAOYSA-N 3-ethyl-3-trimethoxysilyloxolane-2,5-dione Chemical compound CO[Si](OC)(OC)C1(C(=O)OC(C1)=O)CC AMZXVEFLFBLDEM-UHFFFAOYSA-N 0.000 description 1
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-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
- CNODSORTHKVDEM-UHFFFAOYSA-N 4-trimethoxysilylaniline Chemical compound CO[Si](OC)(OC)C1=CC=C(N)C=C1 CNODSORTHKVDEM-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- FMWWGEBUTXJDFV-UHFFFAOYSA-N CN(C)CO[Si](OC)(OC)CC1=CC=CC=C1 Chemical compound CN(C)CO[Si](OC)(OC)CC1=CC=CC=C1 FMWWGEBUTXJDFV-UHFFFAOYSA-N 0.000 description 1
- JQDDASRILBRILN-UHFFFAOYSA-N COC(OC)[SiH2]CC[Si](C)(C)C Chemical compound COC(OC)[SiH2]CC[Si](C)(C)C JQDDASRILBRILN-UHFFFAOYSA-N 0.000 description 1
- DPZRFKBLQTZZFD-UHFFFAOYSA-N COC(OC)[SiH2]C[SiH2]C(OC)OC.C(C)OC(OCC)[SiH2]C[Si](OCC)(OCC)OCC Chemical compound COC(OC)[SiH2]C[SiH2]C(OC)OC.C(C)OC(OCC)[SiH2]C[Si](OCC)(OCC)OCC DPZRFKBLQTZZFD-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- AQZGPSLYZOOYQP-UHFFFAOYSA-N Diisoamyl ether Chemical compound CC(C)CCOCCC(C)C AQZGPSLYZOOYQP-UHFFFAOYSA-N 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
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- YIRZROVNUPFFNZ-UHFFFAOYSA-N trimethoxy-(4-trimethoxysilylphenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=C([Si](OC)(OC)OC)C=C1 YIRZROVNUPFFNZ-UHFFFAOYSA-N 0.000 description 1
- VIPCDVWYAADTGR-UHFFFAOYSA-N trimethyl(methylsilyl)silane Chemical compound C[SiH2][Si](C)(C)C VIPCDVWYAADTGR-UHFFFAOYSA-N 0.000 description 1
- MUCRQDBOUNQJFE-UHFFFAOYSA-N triphenoxy(triphenoxysilyl)silane Chemical compound C=1C=CC=CC=1O[Si]([Si](OC=1C=CC=CC=1)(OC=1C=CC=CC=1)OC=1C=CC=CC=1)(OC=1C=CC=CC=1)OC1=CC=CC=C1 MUCRQDBOUNQJFE-UHFFFAOYSA-N 0.000 description 1
- OLTVTFUBQOLTND-UHFFFAOYSA-N tris(2-methoxyethoxy)-methylsilane Chemical compound COCCO[Si](C)(OCCOC)OCCOC OLTVTFUBQOLTND-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000008096 xylene Substances 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
- G03F7/075—Silicon-containing compounds
- G03F7/0752—Silicon-containing compounds in non photosensitive layers or as additives, e.g. for dry lithography
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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
- G03F1/00—Originals for photomechanical production of textured or patterned surfaces, e.g., masks, photo-masks, reticles; Mask blanks or pellicles therefor; Containers specially adapted therefor; Preparation thereof
- G03F1/68—Preparation processes not covered by groups G03F1/20 - G03F1/50
- G03F1/80—Etching
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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
- G03F7/0002—Lithographic processes using patterning methods other than those involving the exposure to radiation, e.g. by stamping
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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
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/031—Organic compounds not covered by group G03F7/029
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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
- G03F7/094—Multilayer resist systems, e.g. planarising 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
- G03F7/16—Coating processes; Apparatus therefor
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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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/40—Treatment after imagewise removal, e.g. baking
- G03F7/405—Treatment with inorganic or organometallic reagents after imagewise removal
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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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/42—Stripping or agents therefor
- G03F7/422—Stripping or agents therefor using liquids only
- G03F7/425—Stripping or agents therefor using liquids only containing mineral alkaline compounds; containing organic basic compounds, e.g. quaternary ammonium compounds; containing heterocyclic basic compounds containing nitrogen
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
- H01L21/0271—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers
- H01L21/0273—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers characterised by the treatment of photoresist layers
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
- H01L21/033—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising inorganic layers
- H01L21/0332—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising inorganic layers characterised by their composition, e.g. multilayer masks, materials
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
- H01L21/31—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to form insulating layers thereon, e.g. for masking or by using photolithographic techniques; After treatment of these layers; Selection of materials for these layers
- H01L21/3105—After-treatment
- H01L21/311—Etching the insulating layers by chemical or physical means
- H01L21/31105—Etching inorganic layers
- H01L21/31111—Etching inorganic layers by chemical means
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
- H01L21/31—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to form insulating layers thereon, e.g. for masking or by using photolithographic techniques; After treatment of these layers; Selection of materials for these layers
- H01L21/3105—After-treatment
- H01L21/311—Etching the insulating layers by chemical or physical means
- H01L21/31144—Etching the insulating layers by chemical or physical means using masks
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02109—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates
- H01L21/02112—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer
- H01L21/02123—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer the material containing silicon
- H01L21/02126—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer the material containing silicon the material containing Si, O, and at least one of H, N, C, F, or other non-metal elements, e.g. SiOC, SiOC:H or SiONC
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02225—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer
- H01L21/0226—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process
- H01L21/02282—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process liquid deposition, e.g. spin-coating, sol-gel techniques, spray coating
Definitions
- the present invention relates to a pattern forming method.
- pattern miniaturization using a multilayer resist process is progressing in order to obtain a higher degree of integration.
- an inorganic film such as a silicon-containing film is first formed on a substrate, and then a resist film having an etching selectivity different from that of the inorganic film is formed on the inorganic film using a resist composition or the like.
- the mask pattern is transferred by exposure and developed with a developer to obtain a resist pattern.
- the resist pattern is transferred to the inorganic film by dry etching, and the pattern of the inorganic film is finally transferred to the substrate to obtain a substrate on which a desired pattern is formed.
- rework may be performed when a defect occurs when the silicon-containing film or the resist film is patterned.
- the inorganic film is a silicon-containing film
- it is treated with an alkaline stripping solution after the step of treating with an acidic stripping solution containing sulfate ions and / or fluorine ions.
- Wet stripping method see JP 2010-139964 A
- wet stripping composition containing a fluoride source and an ammonium salt see JP 2010-515107 A
- wet using high-concentration hydrogen fluoride water Peeling, dry peeling see JP 2010-85912 A
- the conventional dry stripping method, the acidic stripping solution, and the wet stripping method using a solution containing fluorine ions have a disadvantage that the substrate is seriously damaged.
- the silicon-containing film after dry etching or its residue tends to have low wet peelability, and this improvement is also demanded.
- JP 2010-139964 A Special table 2010-515107 gazette JP 2010-85912 A
- the present invention has been made based on the circumstances as described above, and its purpose is to use a silicon-containing film without using an acidic stripping solution or a fluorine compound that is highly damaging to a substrate, and before and after etching. It is to provide a pattern forming method that can be removed.
- the invention made in order to solve the above problems is a process of forming a resist underlayer film on one side of a substrate (hereinafter also referred to as “resist underlayer film forming process”), opposite to the substrate in the resist underlayer film.
- a step of forming a silicon-containing film on the surface side of the substrate hereinafter also referred to as “silicon-containing film forming step” and a step of removing the silicon-containing film with a basic aqueous solution (hereinafter also referred to as “silicon-containing film removal step”). ).
- the pattern forming method of the present invention it is possible to remove the silicon-containing film without using an acidic stripping solution or a fluorine compound, which causes great damage to the substrate, and before and after etching. Thereby, the silicon-containing film can be formed again and reprocessed. Therefore, the pattern forming method can be applied to the manufacture of semiconductor devices that are expected to be further miniaturized in the future.
- the pattern forming method of the present invention includes a resist underlayer film forming step, a silicon-containing film forming step, and a silicon-containing film removing step.
- the pattern forming method usually includes a step of forming a resist pattern on the surface of the silicon-containing film opposite to the substrate after the silicon-containing film forming step and before the silicon-containing film removing step (hereinafter referred to as “resist”). And a step of etching the silicon-containing film using the resist pattern as a mask (hereinafter also referred to as an “etching step”).
- etching step a step of treating the silicon-containing film with a treatment liquid containing an acid or a fluorine compound after the silicon-containing film forming step and before the silicon-containing film removing step.
- the silicon-containing film can be removed without using an acidic stripping solution or a fluorine compound that causes great damage to the substrate, and before and after etching. Accordingly, the silicon-containing film can be formed again and reprocessed.
- each step will be described.
- a resist underlayer film is formed on one surface side of the substrate.
- the substrate include insulating films such as silicon oxide, silicon nitride, silicon oxynitride, and polysiloxane, and commercially available products such as “Black Diamond” from AMAT, “Silk” from Dow Chemical, and “LKD5109” from JSR.
- An interlayer insulating film such as a wafer coated with a low dielectric insulating film such as Polysilicon, a so-called metal gate film in which a metal component is injected into polysilicon, and the like are also included.
- a patterned substrate such as a wiring groove (trench) or a plug groove (via) may be used.
- the resist underlayer film examples include an organic film formed using a resist underlayer film composition, a carbon film formed by a conventionally known CVD (Chemical Vapor Deposition) method, and the like.
- the resist underlayer film forming composition conventionally known compositions can be used, and examples thereof include NFC HM8005 manufactured by JSR.
- a coating film of the resist underlayer film forming composition is formed by coating on the substrate, and the coating film is cured by heat treatment, or irradiation with ultraviolet light and heat treatment. Can be formed.
- Examples of the method for applying the resist underlayer film forming composition include spin coating, roll coating, and dipping.
- heating temperature 150 degreeC is preferable and 180 degreeC is more preferable.
- an upper limit of heating time 500 degreeC is preferable and 350 degreeC is more preferable.
- 30 seconds are preferred and 45 seconds are more preferred.
- the upper limit of the heating time is preferably 1,200 seconds, and more preferably 600 seconds.
- the lower limit of the average thickness of the resist underlayer film is preferably 50 nm.
- the upper limit of the average thickness is preferably 500 nm.
- another lower layer film different from the resist lower layer film may be formed on the substrate surface or the resist lower layer film.
- the other lower layer film is a film provided with an antireflection function, coating film flatness, high etching resistance against a fluorine-based gas such as CF 4, and the like.
- a commercially available product such as NFC HM8005 manufactured by JSR Corporation can be used.
- a silicon-containing film is formed on the surface of the resist underlayer film opposite to the substrate.
- the silicon-containing film is formed, for example, by applying a silicon-containing film forming composition or the like on the surface of the resist underlayer film opposite to the substrate.
- the silicon-containing film forming composition will be described later. Examples of the method for applying the silicon-containing film forming composition include spin coating, cast coating, roll coating, and the like.
- 10 nm is preferable and 20 nm is more preferable.
- the upper limit of the average thickness is preferably 1,000 nm, more preferably 500 nm, and even more preferably 300 nm.
- the silicon-containing film-forming composition contains [A] polysiloxane and [B] an organic solvent. Moreover, the said silicon-containing film formation composition may contain other arbitrary components, such as a crosslinking accelerator, as a suitable component, unless the effect of this invention is impaired. Hereinafter, each component will be described.
- polysiloxane ⁇ [A] polysiloxane>
- the structure of polysiloxane is not particularly limited, but a hydrolysis condensate of a compound containing a silane compound represented by the following formula (2) (hereinafter also referred to as “silane compound (a)”) Is preferred.
- silane compound (a) a hydrolysis condensate of a compound containing a silane compound represented by the following formula (2)
- R 1 represents a hydrogen atom, a fluorine atom, an alkyl group having 1 to 5 carbon atoms, a cyano group, a cyanoalkyl group, an alkylcarbonyloxy group, an acid anhydride group, an alkenyl group, an aryl group, or an aralkyl. It is a group. This alkyl group may be substituted with a fluorine atom, and the aryl group and the aralkyl group may be substituted.
- X is a halogen atom or —OR 2 .
- R 2 is a monovalent organic group.
- a is an integer of 0 to 3.
- Examples of the alkyl group having 1 to 5 carbon atoms represented by R 1 include linear alkyl groups such as a methyl group, an ethyl group, an n-propyl group, an n-butyl group, and an n-pentyl group; Examples thereof include branched alkyl groups such as isopropyl group, isobutyl group, sec-butyl group, t-butyl group and isoamyl group.
- Examples of the alkyl group having 1 to 5 carbon atoms substituted with a fluorine atom represented by R 1 include, for example, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a fluoroethyl group, a difluoroethyl group, and a trifluoroethyl group.
- Examples of the cyanoalkyl group represented by R 1 include a cyanoethyl group and a cyanopropyl group.
- Examples of the alkylcarbonyloxy group represented by R 1 include a methylcarbonyloxy group, an ethylcarbonyloxy group, a propylcarbonyloxy group, and a butylcarbonyloxy group.
- Examples of the alkenyl group represented by R 1 include a group represented by the following formula (i-1).
- CH 2 CH- (CH 2 ) n- * (i-1)
- n is an integer of 0-4. * Indicates a bond.
- N is preferably 0 or 1, more preferably 0 (vinyl group).
- Examples of the aryl group represented by R 1 include a phenyl group, a naphthyl group, a methylphenyl group, and an ethylphenyl group.
- Examples of the aralkyl group represented by R 1 include a benzyl group, a phenylethyl group, a phenylpropyl group, and a naphthylmethyl group.
- Examples of the substituent that the aryl group and aralkyl group may have include, for example, a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, a hydroxyl group, a carboxyl group, a cyano group, a nitro group, an alkoxy group, and an aryl group.
- a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom
- a hydroxyl group such as a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom
- a hydroxyl group such as a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom
- a hydroxyl group such as a fluorine atom, a chlorine atom, a bromine
- Examples of the halogen atom represented by X include a fluorine atom and a chlorine atom.
- Examples of the monovalent organic group represented by R 2 in —OR 2 include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, and a t-butyl group. Examples thereof include alkyl groups having 1 to 4 carbon atoms such as groups.
- the integer a is preferably an integer from 0 to 2.
- silane compound (a) examples include trifunctional silane compounds such as aromatic ring-containing trialkoxysilane, alkyltrialkoxysilane, alkyltriaryloxysilane, alkenyltrialkoxysilane, alkyltrihalogenosilane, and acid anhydride group-containing trialkoxysilane. And tetrafunctional silane compounds such as tetraalkoxysilane, tetraaryloxysilane, and tetrahalogenosilane.
- trifunctional silane compounds such as aromatic ring-containing trialkoxysilane, alkyltrialkoxysilane, alkyltriaryloxysilane, alkenyltrialkoxysilane, alkyltrihalogenosilane, and acid anhydride group-containing trialkoxysilane.
- tetrafunctional silane compounds such as tetraalkoxysilane, tetraaryloxysilane, and tetrahalogen
- aromatic ring-containing trialkoxysilane examples include, for example, phenyltrimethoxysilane, benzyltrimethoxysilane, phenethyltrimethoxysilane, methylphenyltrimethoxysilane, ethylphenyltrimethoxysilane, methoxyphenyltrimethoxysilane, and phenoxyphenyltriphenyl.
- alkyltrialkoxysilane examples include methyltrimethoxysilane, methyltriethoxysilane, methyltris (dimethylsiloxy) silane, methyltris (methoxyethoxy) silane, ethyltrimethoxysilane, and ethyltriethoxysilane.
- alkenyltrialkoxysilane examples include vinyltrimethoxysilane, vinyltriethoxysilane, allyltrimethoxysilane, and allyltriethoxysilane.
- acid anhydride group-containing trialkoxysilane examples include (trimethoxysilyl) ethyl succinic anhydride, (triethoxysilyl) propyl succinic anhydride, and the like.
- trifunctional silane compounds include methyltriacetoxysilane, methyltrichlorosilane, ethyltriacetoxysilane, ethyltrichlorosilane, methyltriphenoxysilane, ethyltriphenoxysilane, vinyltriphenoxysilane, allyltriphenoxysilane. Etc.
- tetrafunctional silane compound examples include tetramethoxysilane, tetraethoxysilane, tetra-n-propoxysilane, tetra-iso-propoxysilane, tetra-n-butoxysilane, tetra-sec-butoxysilane, tetra-tert- Tetraalkoxysilanes such as butoxysilane; Examples include tetraphenoxysilane and tetrachlorosilane.
- a silane compound having an aromatic ring or a silane compound having an acid anhydride group is preferable, and phenyltrialkoxysilane and (triethoxysilyl) propyl succinic anhydride are more preferable. preferable.
- silane compound for obtaining polysiloxane examples include hexamethoxydisilane, hexaethoxydisilane, hexaphenoxydisilane, 1,1,1,2,2-pentamethoxy- 2-methyldisilane, 1,1,1,2,2-pentaphenoxy-2-phenyldisilane, 1,1,2,2-tetramethoxy-1,2-dimethyldisilane, 1,1,2,2-tetra Ethoxy-1,2-dimethyldisilane, 1,1,2,2-tetraphenoxy-1,2-dimethyldisilane, 1,1,2-trimethoxy-1,2,2-trimethyldisilane, 1,1,2- Triethoxy-1,2,2-trimethyldisilane, 1,1,2-triphenoxy-1,2,2-trimethyldisilane, 1,2-dimethoxy-1,1,2, - tetramethyl disilane, 1,2-diethoxy-1,1,2,2-tetramethyl disilane
- the polysiloxane may be contained in the silicon-containing film forming composition only in one kind, or in two or more kinds.
- the lower limit of the weight average molecular weight (Mw) in terms of polystyrene by gel permeation chromatography (GPC) of polysiloxane is preferably 1,000, more preferably 1,200, and even more preferably 1,500.
- the upper limit of Mw is preferably 20,000, more preferably 15,000, and still more preferably 7,000.
- Mw in this specification is a value measured by gel permeation chromatography using monodisperse polystyrene as a standard substance. Specific measurement conditions will be described later.
- a known hydrolytic condensation method can be used as a method for hydrolyzing and condensing the silane compound (a) and other silane compounds used as necessary.
- the lower limit of the content of polysiloxane is preferably 70% by mass, more preferably 80% by mass, and still more preferably 90% by mass with respect to the total solid content of the silicon-containing film-forming composition.
- the silicon-containing film-forming composition contains [B] an organic solvent.
- the organic solvent is not particularly limited as long as it can dissolve or disperse [A] polysiloxane and an optional component described later.
- organic solvent examples include alcohol solvents, ketone solvents, amide solvents, ether solvents, ester solvents, hydrocarbon solvents, and mixed solvents thereof. These solvents can be used alone or in combination of two or more.
- the alcohol solvent examples include aliphatic monoalcohol solvents having 1 to 18 carbon atoms such as 4-methyl-2-pentanol and n-hexanol; An alicyclic monoalcohol solvent having 3 to 18 carbon atoms such as cyclohexanol; A polyhydric alcohol solvent having 2 to 18 carbon atoms such as 1,2-propylene glycol; Examples thereof include polyhydric alcohol partial ether solvents having 3 to 19 carbon atoms such as propylene glycol monomethyl ether.
- ether solvent examples include dialkyl ether solvents such as diethyl ether, dipropyl ether, dibutyl ether, dipentyl ether, diisoamyl ether, dihexyl ether, and diheptyl ether; Cyclic ether solvents such as tetrahydrofuran and tetrahydropyran; And aromatic ring-containing ether solvents such as diphenyl ether and anisole.
- dialkyl ether solvents such as diethyl ether, dipropyl ether, dibutyl ether, dipentyl ether, diisoamyl ether, dihexyl ether, and diheptyl ether
- Cyclic ether solvents such as tetrahydrofuran and tetrahydropyran
- aromatic ring-containing ether solvents such as diphenyl ether and anisole.
- ketone solvent examples include acetone, methyl ethyl ketone, methyl-n-propyl ketone, methyl-n-butyl ketone, diethyl ketone, methyl-iso-butyl ketone, 2-heptanone, ethyl-n-butyl ketone, and methyl-n-hexyl ketone.
- Chain ketone solvents such as di-iso-butyl ketone and trimethylnonanone: Cyclic ketone solvents such as cyclopentanone, cyclohexanone, cycloheptanone, cyclooctanone and methylcyclohexanone: Examples include 2,4-pentanedione, acetonylacetone, acetophenone, and the like.
- amide solvent examples include cyclic amide solvents such as N, N′-dimethylimidazolidinone and N-methylpyrrolidone; Examples thereof include chain amide solvents such as N-methylformamide, N, N-dimethylformamide, N, N-diethylformamide, acetamide, N-methylacetamide, N, N-dimethylacetamide, and N-methylpropionamide.
- cyclic amide solvents such as N, N′-dimethylimidazolidinone and N-methylpyrrolidone
- chain amide solvents such as N-methylformamide, N, N-dimethylformamide, N, N-diethylformamide, acetamide, N-methylacetamide, N, N-dimethylacetamide, and N-methylpropionamide.
- ester solvent examples include monocarboxylic acid ester solvents such as butyl acetate, ethyl lactate, and butoxymethyl acetate; Polyhydric alcohol carboxylate solvents such as propylene glycol acetate; Polyhydric alcohol partial ether carboxylate solvents such as propylene glycol monomethyl ether acetate; Polycarboxylic acid diester solvents such as diethyl oxalate; Examples thereof include carbonate solvents such as dimethyl carbonate, diethyl carbonate, ethylene carbonate, and propylene carbonate.
- monocarboxylic acid ester solvents such as butyl acetate, ethyl lactate, and butoxymethyl acetate
- Polyhydric alcohol carboxylate solvents such as propylene glycol acetate
- Polyhydric alcohol partial ether carboxylate solvents such as propylene glycol monomethyl ether acetate
- Polycarboxylic acid diester solvents such as diethyl oxalate
- Examples thereof
- hydrocarbon solvent examples include aliphatic hydrocarbon solvents having 5 to 12 carbon atoms such as n-pentane and n-hexane; Examples thereof include aromatic hydrocarbon solvents having 6 to 16 carbon atoms such as toluene and xylene.
- propylene glycol monomethyl ether propylene glycol monoethyl ether, or propylene glycol monomethyl ether acetate is preferred.
- the crosslinking accelerator is a compound that can promote a crosslinking reaction between or within the molecular chains of [A] polysiloxane when a silicon-containing film is formed from the silicon-containing film-forming composition.
- the crosslinking accelerator is not particularly limited as long as it has the above properties, and conventionally known crosslinking accelerators can be used, and examples thereof include acids, bases, metal complexes, metal salt compounds, onium salt compounds and the like.
- a crosslinking accelerator may be used individually by 1 type, and 2 or more types may be mixed and used for it.
- the silicon-containing film-forming composition further contains an acid generator, base generator, surfactant, ⁇ -diketone, colloidal silica, colloidal alumina, organic polymer, and the like as optional components. May be.
- the silicon-containing film-forming composition can be obtained, for example, by mixing [A] polysiloxane, [B] an organic solvent and optional components as necessary, and dissolving or dispersing in [B] the organic solvent.
- [A] polysiloxane [B] an organic solvent and optional components as necessary, and dissolving or dispersing in [B] the organic solvent.
- the upper limit of the solid content concentration of the silicon-containing film-forming composition is preferably 20% by mass, more preferably 15% by mass, and even more preferably 10% by mass.
- the lower limit of the contact angle of the silicon-containing film with respect to pure water is preferably 40 °, particularly preferably 45 °.
- the upper limit of the contact angle is preferably 80 °, and particularly preferably 75 °. In the present specification, unless otherwise specified, the contact angle indicates a measured value at 25 ° C.
- the silicon-containing film is preferably formed from a hydrolysis-condensation product of a composition containing 60 mol% or more of the compound represented by the following formula (1) in all silicon compounds.
- X is a halogen atom or —OR 2 .
- R 2 is a monovalent organic group.
- the silicon-containing film is preferably formed from a hydrolysis condensate of a compound containing 60 mol% or more of a tetrafunctional silane monomer.
- the tetrafunctional silane monomer means one having four hydrolyzable groups on a silicon atom. Examples of the hydrolyzable group include an alkoxy group, an aryloxy group, and a halogeno group.
- the trifunctional silane monomer is equivalent to the bifunctional silane monomer.
- the solvent in the coating film may be volatilized by pre-baking (PB) as necessary.
- PB temperature is appropriately selected depending on the composition of the composition, but the lower limit is preferably 50 ° C.
- the upper limit of the PB temperature is preferably 450 ° C.
- the lower limit of the PB time is preferably 5 seconds.
- the upper limit of the PB time is preferably 600 seconds.
- the silicon-containing film is removed with a basic aqueous solution.
- the silicon-containing film removal step is preferably performed at less than 100 ° C.
- the removal of the silicon-containing film in this step can be performed, for example, by immersing the substrate on which the silicon-containing film is formed in a heated basic aqueous solution.
- As a minimum of the temperature of basic aqueous solution 30 ° C is preferred, 40 ° C is more preferred, and 50 ° C is still more preferred.
- 100 degreeC is preferable, 95 degreeC is more preferable, and 90 degreeC is further more preferable.
- As a minimum of immersion time 1 second is preferred and 10 seconds is more preferred.
- As an upper limit of immersion time 1 hour is preferable and 30 minutes is more preferable. Then, pure water rinse etc. are performed and the basic aqueous solution used is removed.
- the basic aqueous solution examples include an aqueous solution containing at least one nitrogen compound selected from the group consisting of ammonia, organic amines, and tetraalkylammonium. Specifically, ammonia, methylamine, dimethylamine, Examples thereof include aqueous solutions of nitrogen compounds such as trimethylamine, ethylamine, diethylamine, triethylamine, tetramethylammonium hydroxide, and tetraethylammonium hydroxide.
- the basic aqueous solution preferably contains neither hydrogen fluoride nor a salt thereof, nor a fluorine compound salt.
- the lower limit of the water content in the basic aqueous solution is preferably 40% by mass, more preferably 60% by mass, and still more preferably 80% by mass.
- the lower limit of the concentration of these basic aqueous solutions is preferably 0.1% by mass, more preferably 0.5% by mass.
- concentration 40 mass% is preferable and 30 mass% is more preferable.
- the basic aqueous solution is preferably further containing hydrogen peroxide, since the removability of the silicon-containing film is further improved.
- a content rate of hydrogen peroxide 1/500 is preferable as a lower limit of a mass ratio of hydrogen peroxide to a nitrogen compound in a basic aqueous solution.
- the upper limit of the mass ratio is preferably 500.
- the basic aqueous solution is preferably a liquid obtained by mixing ammonia, hydrogen peroxide and water.
- This liquid may be any liquid that can be obtained by mixing ammonia, hydrogen peroxide, and water, and includes liquids in which ammonia and / or hydrogen peroxide is not detected due to a reaction between ammonia and hydrogen peroxide.
- ammonia and hydrogen peroxide or a reaction product of ammonia and hydrogen peroxide and a liquid containing water are preferable, and specific examples thereof include: A liquid containing ammonia, hydrogen peroxide and water; A reaction product of ammonia and hydrogen peroxide, a liquid containing ammonia and water; A reaction product of ammonia and hydrogen peroxide, a liquid containing hydrogen peroxide and water; Examples include a reaction product of ammonia and hydrogen peroxide and a liquid containing water.
- a liquid obtained by mixing ammonia, hydrogen peroxide and water a liquid containing ammonia, hydrogen peroxide and water is preferable.
- the resist film that has not been properly patterned can be removed together with the silicon-containing film by removing the silicon-containing film. Reworking such as forming a resist film again is possible. Moreover, this process can also be performed after forming a pattern in a silicon-containing film
- a resist pattern is formed on the silicon-containing film formed in [Silicon-containing film forming step].
- the resist pattern can be formed by a conventionally known method such as a method using a resist composition or a method using a nanoimprint lithography method.
- the silicon-containing film is etched using the resist pattern as a mask to form a pattern in the silicon-containing film.
- the resist film and the silicon-containing film that have not been properly patterned can be peeled off by the above-described silicon-containing film removing step. And can be patterned.
- the resist underlayer film may be further etched to form a pattern in the resist underlayer film. Thereafter, since the silicon-containing film is removed in the above-described silicon-containing film removal step, a substrate having a patterned resist underlayer film can be obtained, and a pattern can be formed on the substrate using this.
- This step may include a step of further etching the substrate.
- dry etching can be performed using a known dry etching apparatus.
- the source gas during dry etching depends on the elemental composition of the object to be etched, but includes oxygen atoms such as O 2 , CO, and CO 2 , inert gases such as He, N 2 , and Ar, Cl 2 , chlorine gas such as BCl 3 , fluorine gas such as CHF 3 and CF 4 , gas of H 2 and NH 3 , etc. can be used. In addition, these gases can also be mixed and used.
- Weight average molecular weight (Mw) The weight average molecular weight (Mw) was measured by a gel permeation chromatograph using monodisperse polystyrene as a standard. As GPC columns, Tosoh's “G2000HXL”: 2 and “G3000HXL: 1” were used, a differential refractometer was used as a detector, and tetrahydrofuran was used as an eluent. The flow rate was 1.0 mL / min, and the column temperature was 40 ° C.
- the mixture was washed with a methanol / water mixed solution (300 g each) and dried under reduced pressure at 60 ° C. overnight to obtain 45.6 g of a brown solid having a hydroxyl group as a terminal group. It was confirmed by 1 H-NMR that the target precursor Y was obtained.
- the oxalic acid aqueous solution was dripped slowly, and it was made to react at 60 degreeC for 4 hours.
- the flask containing the reaction solution was allowed to cool and then replaced with propylene glycol monomethyl ether acetate, set in an evaporator, and methanol was removed to obtain 473 g of a resin solution.
- the solid content in this resin solution be polysiloxane (A-3).
- the content ratio of the solid content in the obtained resin solution was 7.5% by mass as a result of measurement by a firing method. Further, Mw of polysiloxane (A-3) was 2,000.
- the oxalic acid aqueous solution was dripped slowly, and it was made to react at 60 degreeC for 4 hours.
- the flask containing the reaction solution was allowed to cool and then replaced with propylene glycol monomethyl ether acetate, set in an evaporator, and methanol was removed to obtain 262 g of a resin solution.
- the solid content in this resin solution be polysiloxane (A-4).
- the content ratio of the solid content in the obtained resin solution was 7.5% by mass as a result of measurement by a firing method.
- Mw of polysiloxane (A-4) was 1,800.
- B-1 Propylene glycol monomethyl ether acetate
- B-2 Propylene glycol monoethyl ether
- B-3 Butanediol monomethyl ether
- D-1 Bis (4-t-butylphenyl) iodonium nonafluoro n-butanesulfonate (compound represented by the following formula (D-1))
- E-1 1,3,4,6-tetrakis (methoxymethyl) glycoluril (compound represented by the following formula (E-1))
- TMAH developer resistance Each of the obtained substrates was immersed in a 2.38% by mass TMAH developer (room temperature) for 60 seconds. The average thickness of the film before and after immersion was measured using a spectroscopic ellipsometer (“UV1280E” manufactured by KLA-TENCOR), and the film thickness change rate was calculated from the measured value. The film thickness change rate was obtained from the above formula (a). The solvent resistance was evaluated as “A” (good) when the film thickness change rate was less than 1%, and “B” (bad) when the film thickness change rate was 1% or more.
- a basic aqueous solution containing a TMAH developer and an aqueous ammonia solution as a component without using an acidic stripping solution or a fluorine compound that causes great damage to the substrate.
- the silicon-containing film can be removed.
- the pattern forming method of the present invention it is possible to remove the silicon-containing film without using an acidic stripping solution or a fluorine compound, which causes great damage to the substrate, and before and after etching. Thereby, the silicon-containing film can be formed again and reprocessed. Therefore, the pattern forming method can be applied to the manufacture of semiconductor devices that are expected to be further miniaturized in the future.
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Abstract
Description
本発明のパターン形成方法は、レジスト下層膜形成工程、ケイ素含有膜形成工程、及びケイ素含有膜除去工程を有する。当該パターン形成方法は、通常、上記ケイ素含有膜形成工程後かつ上記ケイ素含有膜除去工程前に、上記ケイ素含有膜における上記基板とは反対の面側にレジストパターンを形成する工程(以下、「レジストパターン形成工程」ともいう)、及び上記レジストパターンをマスクとして上記ケイ素含有膜をエッチングする工程(以下、「エッチング工程」ともいう)をさらに有する。但し、上記ケイ素含有膜形成工程の後かつ上記ケイ素含有膜除去工程前に、上記ケイ素含有膜を酸又はフッ素化合物を含有する処理液により処理する工程を有しない。
本工程では、基板の一方の面側にレジスト下層膜を形成する。上記基板としては、例えば酸化シリコン、窒化シリコン、酸窒化シリコン、ポリシロキサン等の絶縁膜、並びに市販品であるAMAT社の「ブラックダイヤモンド」、ダウケミカル社の「シルク」、JSR社の「LKD5109」等の低誘電体絶縁膜で被覆したウェハ等の層間絶縁膜が挙げられる。ポリシリコンや、ポリシリコン中へ金属成分を注入したいわゆるメタルゲート膜等も含まれる。また、この基板としては、配線溝(トレンチ)、プラグ溝(ビア)等のパターン化された基板を用いてもよい。
本工程では、上記レジスト下層膜における上記基板とは反対の面側にケイ素含有膜を形成する。ケイ素含有膜は、例えばケイ素含有膜形成組成物等を上記レジスト下層膜における上記基板とは反対の面側に塗布することにより形成される。ケイ素含有膜形成組成物については後述する。ケイ素含有膜形成組成物の塗布方法としては、例えば回転塗布、流延塗布、ロール塗布等が挙げられる。なお、形成されるケイ素含有膜の平均厚みの下限としては、10nmが好ましく、20nmがより好ましい。上記平均厚みの上限としては、1,000nmが好ましく、500nmがより好ましく、300nmがさらに好ましい。
ケイ素含有膜形成組成物は、[A]ポリシロキサン及び[B]有機溶媒を含有する。また、上記ケイ素含有膜形成組成物は、本発明の効果を損なわない限り、好適成分として、架橋促進剤等のその他の任意成分を含有してもよい。以下、各成分について説明する。
[A]ポリシロキサンとしては、構造が特に限定されるものではないが、下記式(2)で表されるシラン化合物(以下「シラン化合物(a)」ともいう)を含む化合物の加水分解縮合物が好ましい。このような[A]ポリシロキサンを用いることにより、形成されるレジストパターンのパターン倒れ耐性を向上させることができると共に、得られるケイ素含有膜を後述するケイ素含有膜除去工程において、より効果的に除去することができる。
イソプロピル基、イソブチル基、sec-ブチル基、t-ブチル基、イソアミル基等の分岐鎖状のアルキル基等が挙げられる。
CH2=CH-(CH2)n-* (i-1)
上記式(i-1)中、nは、0~4の整数である。*は、結合手を示す。
上記nとしては、好ましくは0又は1であり、更に好ましくは0(ビニル基)である。
テトラフェノキシシラン、テトラクロロシラン等が挙げられる。
ビス(トリメトキシシリル)メタン、ビス(トリエトキシシリル)メタン、1-(ジメトキシメチルシリル)-1-(トリメトキシシリル)メタン、1-(ジエトキシメチルシリル)-1-(トリエトキシシリル)メタン、ビス(ジメトキシメチルシリル)メタン、ビス(ジエトキシメチルシリル)メタン、ビス(ジメチルメトキシシリル)メタン、ビス(ジメチルエトキシシリル)メタン、1-(ジメトキシメチルシリル)-2-(トリメチルシリル)エタン、1-(ジエトキシメチルシリル)-2-(トリメチルシリル)エタン等のビスシリル基含有シラン類;
1,2-ビス(トリメトキシシリル)ベンゼン、1,2-ビス(トリエトキシシリル)ベンゼン、1,4-ビス(トリメトキシシリル)ベンゼン、1,4-ビス(トリエトキシシリル)ベンゼン等のジシラン類;
ポリジメトキシメチルカルボシラン、ポリジエトキシメチルカルボシラン等のポリカルボシラン等が挙げられる。これらのシラン化合物は、1種単独で用いてもよいし、2種以上を組み合わせて用いてもよい。
上記ケイ素含有膜形成組成物は、[B]有機溶媒を含有する。[B]有機溶媒としては、[A]ポリシロキサン及び後述する任意成分を溶解又は分散できるものであれば特に限定されない。
4-メチル-2-ペンタノール、n-ヘキサノール等の炭素数1~18の脂肪族モノアルコール系溶媒;
シクロヘキサノール等の炭素数3~18の脂環式モノアルコール系溶媒;
1,2-プロピレングリコール等の炭素数2~18の多価アルコール系溶媒;
プロピレングリコールモノメチルエーテル等の炭素数3~19の多価アルコール部分エーテル系溶媒等が挙げられる。
ジエチルエーテル、ジプロピルエーテル、ジブチルエーテル、ジペンチルエーテル、ジイソアミルエーテル、ジヘキシルエーテル、ジヘプチルエーテル等のジアルキルエーテル系溶媒;
テトラヒドロフラン、テトラヒドロピラン等の環状エーテル系溶媒;
ジフェニルエーテル、アニソール等の芳香環含有エーテル系溶媒等が挙げられる。
アセトン、メチルエチルケトン、メチル-n-プロピルケトン、メチル-n-ブチルケトン、ジエチルケトン、メチル-iso-ブチルケトン、2-ヘプタノン、エチル-n-ブチルケトン、メチル-n-ヘキシルケトン、ジ-iso-ブチルケトン、トリメチルノナノン等の鎖状ケトン系溶媒:
シクロペンタノン、シクロヘキサノン、シクロヘプタノン、シクロオクタノン、メチルシクロヘキサノン等の環状ケトン系溶媒:
2,4-ペンタンジオン、アセトニルアセトン、アセトフェノン等が挙げられる。
N,N’-ジメチルイミダゾリジノン、N-メチルピロリドン等の環状アミド系溶媒;
N-メチルホルムアミド、N,N-ジメチルホルムアミド、N,N-ジエチルホルムアミド、アセトアミド、N-メチルアセトアミド、N,N-ジメチルアセトアミド、N-メチルプロピオンアミド等の鎖状アミド系溶媒等が挙げられる。
酢酸ブチル、乳酸エチル、酢酸ブトキシメチル等のモノカルボン酸エステル系溶媒;
プロピレングリコールアセテート等の多価アルコールカルボキシレート系溶媒;
プロピレングリコールモノメチルエーテルアセテート等の多価アルコール部分エーテルカルボキシレート系溶媒;
シュウ酸ジエチル等の多価カルボン酸ジエステル系溶媒;
ジメチルカーボネート、ジエチルカーボネート、エチレンカーボネート、プロピレンカーボネート等のカーボネート系溶媒などが挙げられる。
n-ペンタン、n-ヘキサン等の炭素数5~12の脂肪族炭化水素系溶媒;
トルエン、キシレン等の炭素数6~16の芳香族炭化水素系溶媒等が挙げられる。
(架橋促進剤)
架橋促進剤は、上記ケイ素含有膜形成組成物からケイ素含有膜を形成する際等に、[A]ポリシロキサンの分子鎖間又は分子鎖内における架橋反応を促進することができる化合物である。架橋促進剤としては、上記性質を有する限り、特に限定されず、従来公知のものを使用することができるが、例えば酸、塩基、金属錯体、金属塩化合物、オニウム塩化合物等が挙げられる。架橋促進剤は、1種単独で用いてもよく、2種以上を混合して用いてもよい。
上記ケイ素含有膜形成組成物は、例えば[A]ポリシロキサン、[B]有機溶媒及び必要に応じて任意成分を混合し、[B]有機溶媒に溶解又は分散して得られる。上記ケイ素含有膜形成組成物の固形分濃度の下限としては、0.5質量%が好ましく、1質量%がより好ましい。上記ケイ素含有膜形成組成物の固形分濃度の上限としては、20質量%が好ましく、15質量%がより好ましく、10質量%がさらに好ましい。
本工程では、塩基性水溶液により上記ケイ素含有膜を除去する。上記ケイ素含有膜除去工程は100℃未満で行われることが好ましい。本工程のケイ素含有膜の除去は、例えば加温した塩基性水溶液にケイ素含有膜が形成された基板を浸漬させて処理することにより行うことができる。塩基性水溶液の温度の下限としては、30℃が好ましく、40℃がより好ましく、50℃がさらに好ましい。上記温度の上限としては、100℃が好ましく、95℃がより好ましく、90℃がさらに好ましい。浸漬時間の下限としては、1秒が好ましく、10秒がより好ましい。浸漬時間の上限としては、1時間が好ましく、30分がより好ましい。その後、純水リンス等を行い、使用した塩基性水溶液を除去する。
アンモニア、過酸化水素及び水を含む液;
アンモニアと過酸化水素との反応生成物、アンモニア及び水を含む液;
アンモニアと過酸化水素との反応生成物、過酸化水素及び水を含む液;
アンモニアと過酸化水素との反応生成物及び水を含む液等が挙げられる。これらの中でも、アンモニア、過酸化水素及び水の混合により得られる液としては、アンモニア、過酸化水素及び水を含む液が好ましい。
本工程では、[ケイ素含有膜形成工程]で形成したケイ素含有膜上にレジストパターンを形成する。本工程において、レジストパターンを形成する方法としては、例えばレジスト組成物を用いる方法、ナノインプリントリソグラフィー法を用いる方法等の従来公知の方法で形成することができる。
本工程では、上記レジストパターンをマスクとして上記ケイ素含有膜をエッチングして、シリコン含有膜にパターンを形成する。当該パターン形成方法によれば、エッチング後であっても、適正にパターニングされなかったレジスト膜及びケイ素含有膜を、上述のケイ素含有膜除去工程によって剥離できるため、ケイ素含有膜とレジスト膜とを再度形成してパターン形成することができる。
[A]化合物の構造は、MALDI-TOF-MS(島津製作所社の「SHIMAZU/KRATOSマトリックス支援レーザーイオン化飛行時間型質量分析装置 KOMPACT MALDI IV tDE」)により分子量を、FT-IR(日本分光社の「420型」)により赤外線吸収スペクトル(IR)を、核磁気共鳴装置(日本電子社の「JNM-ECA-500型」)(測定溶媒:DMSO-d6)により1H-NMRスペクトルをそれぞれ測定することにより確認した。
重量平均分子量(Mw)は、単分散ポリスチレンを標準とするゲルパーミエーションクロマトグラフにより測定した。GPCカラムとして東ソー社の「G2000HXL」:2本及び「G3000HXL:1本」を、検出器として示差屈折計を、溶離液としてテトラヒドロフランを用いた。流量1.0mL/分、カラム温度は40℃とした。
[合成例1]((A-1)の合成)
1,000mLの三口ナス型フラスコに、ブチルアクリレート13.28gとメチルイソブチルケトン(MIBK)75gとを加えた。別途滴下槽を設け、そこに2-ビニルナフタレン54.22g、ビニルベンジルアルコール32.50g、及びラジカル重合開始剤(和光純薬工業社の「V-601」)11.91gをMIBK75gに溶解させた。釜温度80℃にて3時間かけて滴下し、その後3時間熟成後、フラスコ釜を溶液温度が室温になるまで冷却した。その後、溶液を5倍質量のヘプタンに滴下し濾過後白色の粉体である化合物(A-1)50.5gを得た。
1,000mLの三口ナス型フラスコに、レゾルシノール35g、アセトアルデヒド39g及びエタノール450gを仕込み、窒素雰囲気下、室温にて溶解させた。得られた溶液に、溶液温度40℃にて、濃塩酸95.6gを1時間かけて滴下し、溶液温度を80℃にして11時間熟成させた。熟成後、フラスコ釜を溶液温度が室温になるまで冷却した。その後、析出してきた赤茶色の固形物を、ろ過にてエタノール溶液を除去することにより回収した。メタノール/水混合溶液(各300g)を用いて掛け流し洗浄を行い、60℃で一晩減圧乾燥し、末端基がヒドロキシ基である茶色の固形物45.6gを得た。1H-NMRにて目的の前駆体Yが得られていることを確認した。
10質量%シュウ酸23.87gと水14.34gを混合し、シュウ酸水溶液を調製した。その後、テトラエトキシシラン55.24g、フェニルトリメトキシシラン7.01g、3-(トリエトキシシリル)プロピルサクシニックアンハイドライド16.14g及びメタノール33.39gを入れたフラスコに、冷却管と、上記調製したシュウ酸水溶液を入れた滴下ロートをセットした。次いで、オイルバスにて60℃に加熱した後、シュウ酸水溶液をゆっくり滴下し、60℃で4時間反応させた。反応終了後、反応溶液の入ったフラスコを放冷してからプロピレングリコールモノメチルエーテルアセテートで置換し、エバポレーターにセットし、メタノールを除去して樹脂溶液473gを得た。この樹脂溶液中における固形分をポリシロキサン(A-3)とする。得られた樹脂溶液中の固形分の含有割合は、焼成法により測定した結果、7.5質量%であった。また、ポリシロキサン(A-3)のMwは2,000であった。
10質量%シュウ酸31.10gと水9.35gを混合し、シュウ酸水溶液を調製した。その後、テトラエトキシシラン64.07g、メチルトリメトキシシラン12.89g、フェニルトリメトキシシラン14.07g及びメタノール68.53gを入れたフラスコに、冷却管と、上記調製したシュウ酸水溶液を入れた滴下ロートをセットした。次いで、オイルバスにて60℃に加熱した後、シュウ酸水溶液をゆっくり滴下し、60℃で4時間反応させた。反応終了後、反応溶液の入ったフラスコを放冷してからプロピレングリコールモノメチルエーテルアセテートで置換し、エバポレーターにセットし、メタノールを除去して樹脂溶液262gを得た。この樹脂溶液中における固形分をポリシロキサン(A-4)とする。得られた樹脂溶液中の固形分の含有割合は、焼成法により測定した結果、7.5質量%であった。また、ポリシロキサン(A-4)のMwは1,800であった。
メタノール200g、イオン交換水200g、及び35質量%塩酸1gを1,000mLガラスフラスコに仕込み、テトラエトキシシラン50g、メチルトリメトキシシラン100g及びフェニルトリメトキシシラン10gの混合物を室温で加えた。そのまま、8時間室温で加水分解縮合させた後、プロピレングリコールモノエチルエーテル300mLを加え、減圧で濃縮して樹脂溶液300g(ポリマー濃度21質量%)を得た。この樹脂溶液中における固形分をポリシロキサン(A-5)とする。また、ポリシロキサン(A-5)のMwは2,000であった。
メタノール200g、イオン交換水200g、及び35質量%塩酸1gを1,000mLガラスフラスコに仕込み、メチルトリメトキシシラン100g及びフェニルトリメトキシシラン20gの混合物を室温で加えた。そのまま8時間室温で加水分解縮合させた後、プロピレングリコールモノエチルエーテル300mLを加え、減圧で濃縮して樹脂溶液300g(ポリマー濃度19質量%)を得た。この樹脂溶液中における固形分をポリシロキサン(A-6)とする。また、ポリシロキサン(A-6)のMwは3,000であった。
イオン交換水260g、65質量%硝酸5g、テトラメトキシシラン70g、メチルトリメトキシシラン70g、及びフェニルトリメトキシシラン10gの混合物を室温で加えた。そのまま、8時間室温で加水分解縮合させた後、ブタンジオールモノメチルエーテル300mLを加え、減圧で濃縮して樹脂溶液300g(ポリマー濃度20質量%)を得た。この樹脂溶液中における固形分をポリシロキサン(A-7)とする。また、ポリシロキサン(A-7)のMwは2,500であった。
レジスト下層膜形成用組成物又はケイ素含有膜形成用組成物の調製に用いた各成分について以下に示す。
B-1:プロピレングリコールモノメチルエーテルアセテート
B-2:プロピレングリコールモノエチルエーテル
B-3:ブタンジオールモノメチルエーテル
D-1:ビス(4-t-ブチルフェニル)ヨードニウムノナフルオロn-ブタンスルホネート(下記式(D-1)で表される化合物)
E-1:1,3,4,6-テトラキス(メトキシメチル)グリコールウリル(下記式(E-1)で表される化合物)
合成例1で得られた(A-1)5質量部をプロピレングリコールモノメチルエーテルアセテート(有機溶媒(B-1))95質量部に溶解させて混合溶液を得た。その後、この混合溶液を孔径0.1μmのメンブランフィルターでろ過してレジスト下層膜形成用組成物(U-1)を調製した。
下記表1に記載の種類及び含有量の成分を用いた以外は、合成例8と同様にしてレジスト下層膜形成用組成物(U-2)を調製した。なお、表1中の「-」は、該当する成分を用いなかったことを示す。
合成例3で得られた(A-3)2質量部をプロピレングリコールモノエチルエーテル(有機溶媒(B-2))98質量部に溶解させて混合溶液を得た。その後、この混合溶液を孔径0.1μmのメンブランフィルターでろ過してケイ素含有膜形成用組成物(U-3)を調製した。
下記表1に記載の種類及び含有量の成分を用いた以外は、合成例10と同様にしてケイ素含有膜形成用組成物(U-4)~(U-7)を調製した。なお、表1中の「-」は、該当する成分を用いなかったことを示す。
[実施例1~4及び比較例1~3]
上記調製した各レジスト下層膜形成用組成物及び各ケイ素含有膜形成用組成物を、シリコンウェハー(基板)上に、スピンコート法により塗布した。その後、大気雰囲気下にて、表2に記載のベーク条件にて各々「レジスト下層膜及びケイ素含有膜付き基板」をそれぞれ得た。
上記得られた各基板を用い、下記項目について、下記方法で評価を行った。評価結果を表3に示す。
上記得られた各基板のケイ素含有膜の純水に対する接触角を、25℃にて測定した。
上記得られた各基板を、シクロヘキサノン(室温)に10秒間浸漬した。浸漬前後の膜の平均厚みを分光エリプソメーター(KLA-TENCOR社の「UV1280E」)を用いて測定し、測定値から膜厚変化率を算出した。膜厚変化率は、下記式(a)より求めた。
膜厚変化率(%)=100×(浸漬後の膜の平均厚みと浸漬前の膜の平均厚みとの差の絶対値)/(浸漬前の膜の平均厚み) (a)
溶媒耐性は、膜厚変化率が1%未満の場合は「A」(良好)と、1%以上の場合は「B」(不良)と評価した。
上記得られた各基板を、2.38質量%TMAH現像液(室温)に60秒間浸漬した。浸漬前後の膜の平均厚みを分光エリプソメーター(KLA-TENCOR社の「UV1280E」)を用いて測定し、測定値から膜厚変化率を算出した。膜厚変化率は上記式(a)より求めた。溶媒耐性は、膜厚変化率が1%未満の場合は「A」(良好)と、1%以上の場合は「B」(不良)と評価した。
上記得られた各基板を、80℃に加温した2.38質量%TMAH現像液に5分間浸漬した。浸漬前後の基板を断面SEMにて観察し、下層のみ残存している場合は「A」(良好)と、ケイ素含有膜が残存している場合は「B」(不良)と評価した。
上記得られた各基板を、65℃に加温したアルカリ性剥離液A(25質量%アンモニア水溶液/30質量%過酸化水素水溶液/水=1/1/5(体積比)混合水溶液)に5分間浸漬した。浸漬前後の基板を断面SEMにて観察し、下層のみ残存している場合は「A」(良好)と、ケイ素含有膜が残存している場合は「B」(不良)と評価した。
Claims (9)
- 基板の一方の面側にレジスト下層膜を形成する工程、
上記レジスト下層膜における上記基板とは反対の面側にケイ素含有膜を形成する工程、及び
塩基性水溶液により上記ケイ素含有膜を除去する工程
を有し、
上記ケイ素含有膜形成工程の後かつ上記ケイ素含有膜除去工程前に、上記ケイ素含有膜を酸又はフッ素化合物を含有する処理液により処理する工程を有しないパターン形成方法。 - 上記塩基性水溶液が、テトラアルキルアンモニウムヒドロキシド及び水を含む液、又はアンモニア、過酸化水素及び水の混合により得られる液である請求項1に記載のパターン形成方法。
- 上記塩基性水溶液がフッ化水素及びその塩並びにフッ素化合物の塩をいずれも含まない請求項1に記載のパターン形成方法。
- 上記ケイ素含有膜除去工程が100℃未満で行われる請求項1に記載のパターン形成方法。
- 上記ケイ素含有膜形成工程後かつ上記ケイ素含有膜除去工程前に、
上記ケイ素含有膜における上記基板とは反対の面側にレジストパターンを形成する工程、及び
上記レジストパターンをマスクとして上記ケイ素含有膜をエッチングする工程
をさらに有する請求項1に記載のパターン形成方法。 - 上記ケイ素含有膜が、
下記式(2)で表される化合物を含むシラン化合物の加水分解縮合物、及び
有機溶媒
を含有する組成物により形成される請求項1に記載のパターン形成方法。
- 上記シラン化合物が芳香環を有する請求項7に記載のパターン形成方法。
- 上記シラン化合物が酸無水物基を有する請求項7に記載のパターン形成方法。
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JP2017092433A (ja) * | 2015-11-06 | 2017-05-25 | Jsr株式会社 | ケイ素含有膜除去方法 |
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US11667620B2 (en) | 2017-09-07 | 2023-06-06 | Jsr Corporation | Composition, film, film-forming method and patterned substrate-producing method |
JP2020100818A (ja) * | 2018-12-20 | 2020-07-02 | キヤノン株式会社 | 液体接着組成物、多層構造体及び該構造体の作製方法 |
Also Published As
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KR20160135216A (ko) | 2016-11-25 |
US20170003592A1 (en) | 2017-01-05 |
KR102388290B1 (ko) | 2022-04-20 |
US10234762B2 (en) | 2019-03-19 |
JPWO2015146524A1 (ja) | 2017-04-13 |
JP6477687B2 (ja) | 2019-03-06 |
TW201610590A (zh) | 2016-03-16 |
TWI654489B (zh) | 2019-03-21 |
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