JP7143763B2 - シリコン含有パターン反転用被覆剤 - Google Patents
シリコン含有パターン反転用被覆剤 Download PDFInfo
- Publication number
- JP7143763B2 JP7143763B2 JP2018501579A JP2018501579A JP7143763B2 JP 7143763 B2 JP7143763 B2 JP 7143763B2 JP 2018501579 A JP2018501579 A JP 2018501579A JP 2018501579 A JP2018501579 A JP 2018501579A JP 7143763 B2 JP7143763 B2 JP 7143763B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- hydrolyzable silane
- polysiloxane
- acid
- pattern
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 229920001296 polysiloxane Polymers 0.000 title claims description 101
- 238000000576 coating method Methods 0.000 title claims description 64
- 239000011248 coating agent Substances 0.000 title claims description 62
- -1 polysiloxane Polymers 0.000 claims description 398
- 239000000203 mixture Substances 0.000 claims description 90
- 229910000077 silane Inorganic materials 0.000 claims description 81
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 80
- 239000000758 substrate Substances 0.000 claims description 79
- 239000002253 acid Substances 0.000 claims description 63
- 125000000217 alkyl group Chemical group 0.000 claims description 45
- 125000003118 aryl group Chemical group 0.000 claims description 41
- 239000002994 raw material Substances 0.000 claims description 33
- 238000004519 manufacturing process Methods 0.000 claims description 32
- 230000003301 hydrolyzing effect Effects 0.000 claims description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 28
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 28
- 229910052710 silicon Inorganic materials 0.000 claims description 26
- 238000005530 etching Methods 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 24
- 239000004065 semiconductor Substances 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 22
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 229910018540 Si C Chemical group 0.000 claims description 14
- 125000005372 silanol group Chemical group 0.000 claims description 14
- 229910010271 silicon carbide Chemical group 0.000 claims description 14
- 239000007787 solid Substances 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 11
- 125000004423 acyloxy group Chemical group 0.000 claims description 11
- 125000004171 alkoxy aryl group Chemical group 0.000 claims description 11
- 125000003700 epoxy group Chemical group 0.000 claims description 11
- 125000000962 organic group Chemical group 0.000 claims description 11
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 11
- 238000011161 development Methods 0.000 claims description 9
- 238000010494 dissociation reaction Methods 0.000 claims description 8
- 230000005593 dissociations Effects 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 description 32
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 25
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 25
- 239000003054 catalyst Substances 0.000 description 25
- 229910052719 titanium Inorganic materials 0.000 description 25
- 239000010936 titanium Substances 0.000 description 25
- 229910052726 zirconium Inorganic materials 0.000 description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 238000006460 hydrolysis reaction Methods 0.000 description 23
- 230000007062 hydrolysis Effects 0.000 description 22
- 239000007983 Tris buffer Substances 0.000 description 21
- 125000004432 carbon atom Chemical group C* 0.000 description 21
- 150000001450 anions Chemical class 0.000 description 19
- 229920002120 photoresistant polymer Polymers 0.000 description 19
- 229920000642 polymer Polymers 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 14
- 229940093858 ethyl acetoacetate Drugs 0.000 description 14
- 239000010703 silicon Substances 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 150000004820 halides Chemical class 0.000 description 13
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 12
- 125000005595 acetylacetonate group Chemical group 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000007789 gas Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 10
- 150000007942 carboxylates Chemical class 0.000 description 10
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 10
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 9
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000003513 alkali Substances 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 9
- 238000004090 dissolution Methods 0.000 description 9
- 229910052736 halogen Inorganic materials 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 9
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
- 239000004094 surface-active agent Substances 0.000 description 8
- IUVCFHHAEHNCFT-INIZCTEOSA-N 2-[(1s)-1-[4-amino-3-(3-fluoro-4-propan-2-yloxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-6-fluoro-3-(3-fluorophenyl)chromen-4-one Chemical compound C1=C(F)C(OC(C)C)=CC=C1C(C1=C(N)N=CN=C11)=NN1[C@@H](C)C1=C(C=2C=C(F)C=CC=2)C(=O)C2=CC(F)=CC=C2O1 IUVCFHHAEHNCFT-INIZCTEOSA-N 0.000 description 7
- 239000011230 binding agent Substances 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000010894 electron beam technology Methods 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- 150000007524 organic acids Chemical class 0.000 description 7
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 7
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 6
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 6
- 239000013522 chelant Substances 0.000 description 6
- 239000008199 coating composition Substances 0.000 description 6
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 6
- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 description 6
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 6
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 6
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 6
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 6
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 5
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 5
- 239000004793 Polystyrene Substances 0.000 description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 239000013065 commercial product Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000001312 dry etching Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 5
- 239000011976 maleic acid Substances 0.000 description 5
- 239000011259 mixed solution Substances 0.000 description 5
- 229920003986 novolac Polymers 0.000 description 5
- 229920002223 polystyrene Polymers 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 5
- 229910021642 ultra pure water Inorganic materials 0.000 description 5
- 239000012498 ultrapure water Substances 0.000 description 5
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 4
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 description 4
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- 239000005711 Benzoic acid Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000004380 ashing Methods 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 235000010233 benzoic acid Nutrition 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 229940006460 bromide ion Drugs 0.000 description 4
- NMJJFJNHVMGPGM-UHFFFAOYSA-N butyl formate Chemical compound CCCCOC=O NMJJFJNHVMGPGM-UHFFFAOYSA-N 0.000 description 4
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 4
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 4
- PGMYKACGEOXYJE-UHFFFAOYSA-N pentyl acetate Chemical compound CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 4
- 150000003003 phosphines Chemical class 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- 239000012953 triphenylsulfonium Substances 0.000 description 4
- 235000012431 wafers Nutrition 0.000 description 4
- DMFAHCVITRDZQB-UHFFFAOYSA-N 1-propoxypropan-2-yl acetate Chemical compound CCCOCC(C)OC(C)=O DMFAHCVITRDZQB-UHFFFAOYSA-N 0.000 description 3
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- MRABAEUHTLLEML-UHFFFAOYSA-N Butyl lactate Chemical compound CCCCOC(=O)C(C)O MRABAEUHTLLEML-UHFFFAOYSA-N 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229940022663 acetate Drugs 0.000 description 3
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 150000001502 aryl halides Chemical class 0.000 description 3
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
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- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229940100515 sorbitan Drugs 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 235000011071 sorbitan monopalmitate Nutrition 0.000 description 1
- 239000001570 sorbitan monopalmitate Substances 0.000 description 1
- 229940031953 sorbitan monopalmitate Drugs 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 239000001589 sorbitan tristearate Substances 0.000 description 1
- 235000011078 sorbitan tristearate Nutrition 0.000 description 1
- 229960004129 sorbitan tristearate Drugs 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- SFZCNBIFKDRMGX-UHFFFAOYSA-N sulfur hexafluoride Chemical compound FS(F)(F)(F)(F)F SFZCNBIFKDRMGX-UHFFFAOYSA-N 0.000 description 1
- 229960000909 sulfur hexafluoride Drugs 0.000 description 1
- LTWFAYWMPMMDGT-UHFFFAOYSA-N tert-butyl 3-oxohexaneperoxoate;titanium Chemical compound [Ti].CCCC(=O)CC(=O)OOC(C)(C)C.CCCC(=O)CC(=O)OOC(C)(C)C LTWFAYWMPMMDGT-UHFFFAOYSA-N 0.000 description 1
- NVQCTSGVFRPZCZ-UHFFFAOYSA-N tert-butyl 3-oxohexaneperoxoate;zirconium Chemical compound [Zr].CCCC(=O)CC(=O)OOC(C)(C)C.CCCC(=O)CC(=O)OOC(C)(C)C NVQCTSGVFRPZCZ-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003866 tertiary ammonium salts Chemical class 0.000 description 1
- MCZDHTKJGDCTAE-UHFFFAOYSA-M tetrabutylazanium;acetate Chemical compound CC([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC MCZDHTKJGDCTAE-UHFFFAOYSA-M 0.000 description 1
- BRGJIIMZXMWMCC-UHFFFAOYSA-N tetradecan-2-ol Chemical compound CCCCCCCCCCCCC(C)O BRGJIIMZXMWMCC-UHFFFAOYSA-N 0.000 description 1
- TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical compound FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- MRYQZMHVZZSQRT-UHFFFAOYSA-M tetramethylazanium;acetate Chemical compound CC([O-])=O.C[N+](C)(C)C MRYQZMHVZZSQRT-UHFFFAOYSA-M 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- JOHWNGGYGAVMGU-UHFFFAOYSA-N trifluorochlorine Chemical compound FCl(F)F JOHWNGGYGAVMGU-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- XMUJIPOFTAHSOK-UHFFFAOYSA-N undecan-2-ol Chemical compound CCCCCCCCCC(C)O XMUJIPOFTAHSOK-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
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- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
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- C09D183/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
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Description
[1] 加水分解性シラン原料の加水分解縮合物を含むポリシロキサンと溶媒とを含む、有機パターン上に塗布される有機パターン平坦化用組成物であって、
上記ポリシロキサンが、Si原子に対し、シラノール基を20モル%以下の割合で含むものであり、
上記ポリシロキサンの重量平均分子量が1,000~50,000である、該組成物。
[2] 上記ポリシロキサンが、式(1):
(式(1)中、R1はアルキル基、アリール基、ハロゲン化アルキル基、ハロゲン化アリール基、アルコキシアリール基、アルケニル基、又はエポキシ基、アクリロイル基、メタクリロイル基、メルカプト基、もしくはシアノ基を有する有機基で且つSi-C結合によりケイ素原子と結合しているものであり、R2はアルコキシ基、アシルオキシ基、又はハロゲン基を示し、aは1を示す。)で示される加水分解性シランを含む加水分解性シラン原料の加水分解縮合物を含む、[1]に記載の組成物。
[3] 上記ポリシロキサンが、上記式(1)で示され、aが1である加水分解性シランを100~50モル%、好ましくは95~50モル%、及び上記式(1)で示され、aが2である加水分解性シランを0~50モル%、好ましくは5~50モル%となる割合で含む加水分解性シラン原料の加水分解縮合物を含む、[2]に記載の組成物。
[4] 上記ポリシロキサンが、上記式(1)のaが0の加水分解性シランを0~100モル%、好ましくは1~100モル%、及びaが1である加水分解性シランを0~100モル%、好ましくは0~99モル%となる割合で含む加水分解性シラン原料の加水分解縮合物のアルコール及び酸による脱水処理生成物である、[2]又は[3]に記載の組成物。
[5] 上記ポリシロキサンが、上記式(1)のaが1又は2の加水分解性シラン原料の加水分解縮合物の非アルコールと弱酸又は塩基とによる処理生成物である、[2]又は[3]にいずれか1項に記載の組成物。
[6] 弱酸が4~5の酸解離定数を有する酸である、[5]に記載の組成物。
[7] 上記有機パターンがレジストパターン、ナノインプリントパターン及び有機下層膜パターンの中から選ばれる、[1]~[6]のいずれか1項に記載の組成物。
[8] 基板上に有機パターンを形成する工程(1)、有機パターンに[1]~[7]のいずれか1項に記載の組成物を塗布する工程(3)、有機パターンをエッチング除去してパターンを反転させる工程(4)、を含む半導体装置の製造方法。
[9] 基板上にレジストを形成する工程(1a)、レジストを露光と現像する工程(2)、現像中又は現像後のレジストパターンに[1]~[7]のいずれか1項に記載の組成物を塗布する工程(3a)、レジストパターンをエッチング除去してパターンを反転させる工程(4a)、を含む半導体装置の製造方法。
[10] 工程(1a)の前に、基板上にレジスト下層膜を形成する工程(1a-1)を含む、[9]に記載の製造方法。
[11] 工程(3)の後に、塗膜表面をエッチバックして有機パターン表面を露出する工程(3-1)を含む、[8]に記載の製造方法。
[12] 有機パターンに塗布される段差基板平坦化用組成物に含まれるポリシロキサンの製造方法であって、
式(1):
(式(1)中、R1はアルキル基、アリール基、ハロゲン化アルキル基、ハロゲン化アリール基、アルコキシアリール基、アルケニル基、又はエポキシ基、アクリロイル基、メタクリロイル基、メルカプト基、もしくはシアノ基を有する有機基で且つSi-C結合によりケイ素原子と結合しているものであり、R2はアルコキシ基、アシルオキシ基、又はハロゲン基を示し、aは0を示す。)で示され、aが0の加水分解性シランを0~100モル%、好ましくは1~100モル%、及び式(1)で示され、aが1である加水分解性シランを0~100モル%、好ましくは0~99モル%となる割合で含む加水分解性シラン原料の加水分解縮合物を、アルコールと酸で脱水処理する工程を含む、製造方法。
[13] 有機パターンに塗布される段差基板平坦化用組成物に含まれるポリシロキサンの製造方法であって、
式(1):
(式(1)中、R1はアルキル基、アリール基、ハロゲン化アルキル基、ハロゲン化アリール基、アルコキシアリール基、アルケニル基、又はエポキシ基、アクリロイル基、メタクリロイル基、メルカプト基、もしくはシアノ基を有する有機基で且つSi-C結合によりケイ素原子と結合しているものであり、R2はアルコキシ基、アシルオキシ基、又はハロゲン基を示し、aは1又は2を示す。)で示され、aが1又は2の加水分解性シラン原料の加水分解縮合物を、非アルコールと弱酸又は塩基とで処理する工程を含む、製造方法。
本発明に係る段差基板平坦化用組成物について以下に説明する。
上記ポリシロキサン中のシラノール基比率は1H NMRにて算出できる。
(式(1)中、R1はアルキル基、アリール基、ハロゲン化アルキル基、ハロゲン化アリール基、アルコキシアリール基、アルケニル基、又はエポキシ基、アクリロイル基、メタクリロイル基、メルカプト基、もしくはシアノ基を有する有機基で且つSi-C結合によりケイ素原子と結合しているものであり、R2はアルコキシ基、アシルオキシ基、又はハロゲン基を示し、aは1を示す。)で示される加水分解性シランを含む加水分解性シラン原料の加水分解縮合物を含む。
さらに好ましくは、式(1)中aが1である加水分解性シランを95~70モル%及び、式(1)中aが2である加水分解性シランを5~30モル%となる割合で含む。
また、酸は、70~160℃の沸点を有する酸が好ましい。例えば、トリフルオロ酢酸、イソ酪酸、酢酸等が挙げられる。
上記の酸は、酸解離定数(pka)が4~5であるか、又は沸点が70~160℃であるか、いずれかの物性を有するものが好ましい。即ち、酸性度が弱いものか、又は酸性度は強くても沸点が低いものを用いることができる。
そして、酸としては酸解離定数、沸点の性質からいずれの性質を利用することも可能であるが、両方の性質を持つ酢酸は好ましく用いることができる。
本発明ではレジストの露光後に用いられる塗布用組成物であるため、マスクを通じてレジストの露光し現像中又は現像後に上記組成物で充填される。
これにより後のドライエッチング工程で、ガス種の選定により、レジストを選択的にドライエッチング除去して充填した加水分解縮合物(ポリシロキサン)による新たなパターンが形成される。
段差基板平坦化用組成物に含まれていても良いその他の成分について以下に説明する。
(但し、mは2~11、nは2~3の整数を、R21はアルキル基又はアリール基を、Y-は陰イオンを示す。)で示される構造を有する第4級アンモニウム塩、
式(D-2):
(但し、R22、R23、R24及びR25はアルキル基又はアリール基を、Nは窒素原子を、Y-は陰イオンを示し、且つR22、R23、R24、及びR25はそれぞれC-N結合により窒素原子と結合されているものである)で示される構造を有する第4級アンモニウム塩、
式(D-3):
(但し、R26及びR27はアルキル基又はアリール基を、Y-は陰イオンを示す)の構造を有する第4級アンモニウム塩、
式(D-4):
(但し、R28はアルキル基又はアリール基を、Y-は陰イオンを示す)の構造を有する第4級アンモニウム塩、
式(D-5):
(但し、R29及びR30はアルキル基又はアリール基を、Y-は陰イオンを示す)の構造を有する第4級アンモニウム塩、
式(D-6):
(但し、mは2~11、nは2~3の整数を、Hは水素原子を、Y-は陰イオンを示す)の構造を有する第3級アンモニウム塩が上げられる。
(但し、R31、R32、R33、及びR34はアルキル基又はアリール基を、Pはリン原子を、Y-は陰イオンを示し、且つR31、R32、R33、及びR34はそれぞれC-P結合によりリン原子と結合されているものである)で示される第4級ホスホニウム塩が上げられる。
(但し、R35、R36、及びR37はアルキル基又はアリール基を、Sは硫黄原子を、Y-は陰イオンを示し、且つR35、R36、及びR37はそれぞれC-S結合により硫黄原子と結合されているものである)で示される第3級スルホニウム塩が上げられる。
以下本発明の半導体基板の平坦化方法を含む半導体装置の製造方法の一例を以下に説明する。また、概要を図5に示す。
なお、本発明にいう段差基板としては、MEMSデバイス向けのウエハが挙げられる。例えば、(1b)ボッシュ法もしくはアルカリ水により段差が形成されたシリコンウエハで、片面にこの段差を有するもの、(2b)同様にシリコンウエハとシリコンウエハの間にシリコン酸化膜が存在しるSOI(Silicon on Insulator)ウエハで、片面段差を有するもの、(3b)ガリウムヒ素基板で、片面に段差形状を有するもの、(4b)シリコンウエハ上に金属・絶縁膜が形成されていて、片面に段差形状を有するものなどが例示される。
上記有機パターンは、フォトレジストパターン、下層半導体基板のエッチングマスクとして機能するレジスト下層膜(塗布型又は蒸着型)パターン、ナノインプリントにて形成されたパターンである。
工程(1a)に用いられるフォトレジストとしては露光に使用される光に感光するものであれば特に限定はない。ネガ型フォトレジスト及びポジ型フォトレジストのいずれも使用できる。ノボラック樹脂と1,2-ナフトキノンジアジドスルホン酸エステルとからなるポジ型フォトレジスト、酸により分解してアルカリ溶解速度を上昇させる基を有するバインダーと光酸発生剤からなる化学増幅型フォトレジスト、酸により分解してフォトレジストのアルカリ溶解速度を上昇させる低分子化合物とアルカリ可溶性バインダーと光酸発生剤とからなる化学増幅型フォトレジスト、及び酸により分解してアルカリ溶解速度を上昇させる基を有するバインダーと酸により分解してフォトレジストのアルカリ溶解速度を上昇させる低分子化合物と光酸発生剤からなる化学増幅型フォトレジストなどがある。例えば、シプレー社製商品名APEX-E、住友化学工業(株)製商品名PAR710、及び信越化学工業(株)製商品名SEPR430等が挙げられる。また、例えば、Proc.SPIE,Vol.3999,330-334(2000)、Proc.SPIE,Vol.3999,357-364(2000)、やProc.SPIE,Vol.3999,365-374(2000)に記載されているような、含フッ素原子ポリマー系フォトレジストを挙げることができる。
工程(2)において、所定のマスクを通して露光が行なわれる。露光には、KrFエキシマレーザー(波長248nm)、ArFエキシマレーザー(波長193nm)及びEUV(波長13.5nm)等を使用することができる。露光後、必要に応じて露光後加熱(post exposure bake)を行なうこともできる。露光後加熱は、加熱温度70℃~150℃、加熱時間0.3~10分間から適宜、選択された条件で行われる。次いで、現像液によって現像が行なわれる。これにより、例えばポジ型フォトレジストが使用された場合は、露光された部分のフォトレジストが除去され、フォトレジストのパターンが形成される。
工程(3)として、現像中又は現像後のレジストに、本発明に係る段差基板平坦化用組成物を塗布・焼成してポリシロキサン被覆膜を作製することにより、該レジストのパターン間を該組成物で埋め込んだポリシロキサン組成物膜を形成する。塗布された段差基板平坦化用組成物の焼成は加熱温度50~180℃で0.5~5分間行われる。ポリシロキサン被覆膜のIso-denseバイアスは50nm以下とする。なお、ポリシロキサン被覆膜のIso-denseバイアスとは、上記段差基板の膜と接する側の界面からポリシロキサン被覆膜の大気と接する側の界面までの長さの最も小さい箇所と最も大きい箇所との膜厚差をいう。具体的には、以下で表されるbの長さがIso-denseバイアスである。図中、aは密のスペース部の中心でのポリシロキサン被覆膜の凹み深さであり、bはオープンスペース部の中心でのポリシロキサン被覆膜の凹み深さであり、cは使用した段差基板における当初のスペースの深さであり、 dはポリシロキサン被覆膜であり、eは段差基板である。段差基板は有機パターン(フォトレジストパターン、下層半導体基板のエッチングマスクとして機能するレジスト下層膜(塗布型又は蒸着型)パターン、ナノインプリントにて形成されたパターン等)基板とすることができる。
また、本工程において、第一被覆用ポリシロキサンを含む第一被覆用ポリシロキサン組成物を塗布・焼成して第一ポリシロキサン被覆膜を作製し、第一ポリシロキサン被覆膜の上に、第一被覆用ポリシロキサンとは異なる第二被覆用ポリシロキサンを含む第二被覆用ポリシロキサン組成物を塗布・焼成して第二ポリシロキサン被覆膜を作製することにより、該レジストのパターン間を該組成物で埋め込んだポリシロキサン組成物膜を形成することもできる。図5(3)、(4)にはこの態様を示した。この場合、少なくとも第二被覆用ポリシロキサン組成物は本発明に係る段差基板平坦化用組成物とすべきであるが、第一被覆用ポリシロキサン組成物は公知の任意のポリシロキサン組成物を適宜選択して使用することができる。塗布された被覆用ポリシロキサン組成物の焼成はそれぞれ、加熱温度50~180℃で0.5~5分間行われる。第二ポリシロキサン被覆膜のIso-denseバイアスは50nm以下とする。
工程(4)ではレジストパターンをエッチング除去してパターンを反転させる。工程(4)において、ドライエッチングはテトラフルオロメタン、パーフルオロシクロブタン(C4F8)、パーフルオロプロパン(C3F8)、トリフルオロメタン、一酸化炭素、アルゴン、酸素、窒素、六フッ化硫黄、ジフルオロメタン、三フッ化窒素及び三フッ化塩素等のガスを用いて行われる。特に酸素系のガスによりドライエッチングが行われることが好ましい。
ビニルトリメトキシシラン30.0g(80mol%)、ジメチルジエトキシシラン7.5g(20mol%)およびプロピレングリコールモノメチルエーテルアセテート56gを300mlのフラスコに入れ、そのフラスコ内の混合溶液をマグネチックスターラーにて撹拌しながら、0.01mol/Lの酢酸16.4gをその混合溶液に滴下した。滴下後、95℃に調整されたオイルバスにフラスコを移し、24時間反応させた。その後、反応溶液を室温まで冷却し、その反応溶液にプロピレングリコールモノメチルエーテルアセテートを19g加え、アセトン、水及び酢酸、並びに反応副生物であるエタノールを反応溶液から減圧留去し濃縮して、共加水分解縮合物(ポリマー)のプロピレングリコールモノメチルエーテルアセテート溶液を得た。固形分濃度は140℃における固形残物換算で30質量%となるように調整した。
作成したポリマー溶液15gを100mlフラスコに移し、100℃に調整されたオイルバス中で12時間反応させた。GPCによる重量平均分子量Mwはポリスチレン換算で10,000であった。
35質量%のテトラエチルアンモニウムヒドロキシド水溶液17.0g、2-プロパノール27.4g、テトラヒドロフラン54.8gを200mlナスフラスコに入れ、そのフラスコ内の混合溶液をマグネチックスターラーにて撹拌しながら、ビニルトリメトキシシラン9.0g(30mol%)、メチルトリエトキシシラン25.3g(70mol%)を滴下した。滴下後、85℃に調整されたオイルバスにフラスコを移し、加温還流下で4時間反応させた。その後、反応溶液を室温まで冷却して500mlの分液ロートに移した。分液ロートに酢酸エチル100g、6規定塩酸34g、超純水68gを加え、分液操作を行い、酢酸エチル層を得た。得られた酢酸エチル層に68gの超純水を加え、洗浄を行った。洗浄操作をさらに1度繰り返し、得られた酢酸エチル層をエバポレーターにより減圧濃縮した。得られた加水分解縮合物(ポリマー)の酢酸エチル溶液の固形分濃度は140℃における固形残物換算で20質量%となるように調整した。GPCによる重量平均分子量Mwはポリスチレン換算で4,000であった。
テトラエトキシシラン53.9g(50mol%)、メチルトリエトキシシラン46.1g(50mol%)およびアセトン100gを500mlのフラスコに入れ、そのフラスコ内の混合溶液をマグネチックスターラーにて撹拌しながら、0.01mol/Lの塩酸32.6gをその混合溶液に滴下した。滴下後、85℃に調整されたオイルバスにフラスコを移し、加温還流下で4時間反応させた。その後、反応溶液を室温まで冷却し、その反応溶液に4-メチル-2-ペンタノールを100g加え、アセトン、水及び塩酸、並びに反応副生物であるエタノールを反応溶液から減圧留去し濃縮して、共加水分解縮合物(ポリマー)の4-メチル-2-ペンタノール溶液を得た。固形分濃度は140℃における固形残物換算で13質量%となるように調整した。GPCによる重量平均分子量Mwはポリスチレン換算で1,400であった。
ポリマー中のシラノール基比率は1H NMRにて算出した。測定はJNM-ECA500(JEOL製)を用いて行った。まずトリエトキシメチルシランまたはジメチルジエトキシシランのメチルプロトンの化学シフト値(0.0-0.6ppm)の積分比を取り基準とした場合、シラノール基は5-7ppmでブロードなピークとして検出される。この5-7ppmの積分比を比較することで、ポリマー中のSi原子1個に対するシラノール基の比率(モル%)を算出した。
また一部ポリマーによっては5-7ppmにシラノール基以外のシランモノマー構造に由来する化学シフトが検出されてしまうことがあるため、見かけ上、シラノール基が多く検出されてしまうことがある。トリエトキシメチルシランまたはジメチルジエトキシシランとその他の構成シランモノマーの配合比率が既存であるため、トリエトキシメチルシランまたはジメチルジエトキシシランメチルプロトンの積分比から、構成シランモノマーの5-7ppmで検出されるモノマー由来ピークの積分比を見積もることができる。シラノール基と同一の化学シフトの範囲に化学シフトを持つシランモノマーを加える場合は、上記のようにして構成シランモノマーの積分比分を差し引くことで正味のシラノール量を算出した。
上記方法で算出された各合成例ポリマーおよび市販のポリシルセスキオキサン樹脂(製品名:SR―13H(小西化学製, 実施例A3))のシラノール量は下記のようになった。
〔塗布液の調製〕
上記合成例A1、A2及び比較合成例A1で得られたポリマー並びに上記SR―13Hの各々と、酸、硬化触媒、溶媒、超純水とを表1に示す割合で混合し、塗布膜形成組成物をそれぞれ調製した。表1中のポリマーの添加割合はポリマー溶液の添加量ではなく、ポリマー自体の添加量を示した。表1中でマレイン酸はMA、N-(3-トリエトキシシリプロピル)-4,5-ジヒドロイミダゾールはIMIDTEOS、4-メチル-2-ペンタノールはMIBC、プロピレングリコールモノメチルエーテルアセテートはPGMEA、プロピレングリコールモノエチルエーテルはPGEE、プロピレングリコールモノメチルエーテルはPGME、超純水はDIWと略した。各添加量は質量部で示した。
〔塗布液の平坦化性(Si基板上での平坦化性評価)〕
実施例A1、A2、A3および比較例A1における各被覆用ポリシロキサン組成物について、下記のように平坦化性評価を行った。その評価結果を表2に示す。
溝の深さ220nm、幅800nmの段差基板上に、スピンコーターを用いて、回転数1500rpm、60秒間の条件にて、実施例A1、A2、A3、比較例A1の各被覆用ポリシロキサン組成物を塗布し、その後110℃のホットプレート上で1分間乾燥することにより、ポリシロキサン被覆膜を形成した。ポリシロキサン被覆膜の膜厚は90nmとした。次いで、得られたポリシロキサン被覆膜について、断面SEMにより断面の形状を観察し平坦化性を評価した。深さ220nm、幅800nmの溝パターンを観察し、溝底部を基準として膜厚(すなわち、シリコン基板の膜と接する側の界面からポリシロキサン被覆膜の大気と接する側の界面までの長さ)の最も小さい箇所と最も大きい箇所の膜厚を測定し、膜厚差を算出し、膜厚差が少ないものほど平坦化性が良好と評価した。また評価に使用したSEM写真を図1~4に記載する。
2:有機下層膜
3:レジスト組成物
4:第一ポリシロキサン被覆膜
5:第二ポリシロキサン被覆膜
a:密のスペース部の中心でのポリシロキサン被覆膜の凹み深さ
b:オープンスペース部の中心でのポリシロキサン被覆膜の凹み深さ
c:使用した段差基板における当初のスペースの深さ
d:ポリシロキサン被覆膜
e:段差基板
Claims (23)
- 加水分解性シラン原料の加水分解縮合物を含むポリシロキサンと溶媒とを含む、有機パターン上に塗布される有機パターン平坦化用組成物であって、
上記組成物の全成分から溶媒を除いた固形分が、0.1質量%以上、10.0質量%未満であり、
上記ポリシロキサンが、Si原子に対し、シラノール基を20モル%以下の割合で含むものであり、
上記ポリシロキサンの重量平均分子量が1,000~50,000である、該組成物。 - レジストパターンを反転させる工程に用いるための、請求項1に記載の組成物。
- 上記ポリシロキサンが、上記式(1)で示され、aが1である加水分解性シランを100~50モル%、及び上記式(1)で示され、aが2である加水分解性シランを0~50モル%となる割合で含む加水分解性シラン原料の加水分解縮合物を含む、請求項3に記載の組成物。
- 上記ポリシロキサンが、上記式(1)で示され、aが1である加水分解性シランを100~50モル%、及び上記式(1)で示され、aが2である加水分解性シランを0~50モル%となる割合で含む加水分解性シラン原料の加水分解縮合物の非アルコールと弱酸又は塩基とによる処理生成物である、請求項4に記載の組成物。
- 弱酸が4~5の酸解離定数を有する酸である、請求項6に記載の組成物。
- 上記有機パターンがレジストパターン、ナノインプリントパターン及び有機下層膜パターンの中から選ばれる、請求項1~7のいずれか1項に記載の組成物。
- 基板上に有機パターンを形成する工程(1)、有機パターンに有機パターン平坦化用組成物を塗布する工程(3)、有機パターンをエッチング除去してパターンを反転させる工程(4)、を含む半導体装置の製造方法であって、
前記有機パターン平坦化用組成物が加水分解性シラン原料の加水分解縮合物を含むポリシロキサンと溶媒とを含み、上記ポリシロキサンが、Si原子に対し、シラノール基を20モル%以下の割合で含むものであり、上記ポリシロキサンの重量平均分子量が1,000~50,000である、半導体装置の製造方法。 - 上記ポリシロキサンが、上記式(1)で示され、aが1である加水分解性シランを100~50モル%、及び上記式(1)で示され、aが2である加水分解性シランを0~50モル%となる割合で含む加水分解性シラン原料の加水分解縮合物を含む、請求項10に記載の製造方法。
- 上記ポリシロキサンが、上記式(1)で示され、aが1である加水分解性シランを100~50モル%、及び上記式(1)で示され、aが2である加水分解性シランを0~50モル%となる割合で含む加水分解性シラン原料の加水分解縮合物の非アルコールと弱酸又は塩基とによる処理生成物である、請求項11に記載の製造方法。
- 弱酸が4~5の酸解離定数を有する酸である、請求項13に記載の製造方法。
- 上記有機パターンがレジストパターン、ナノインプリントパターン及び有機下層膜パターンの中から選ばれる、請求項9~14のいずれか1項に記載の製造方法。
- 基板上にレジストを形成する工程(1a)、レジストを露光と現像する工程(2)、現像中又は現像後のレジストパターンに有機パターン平坦化用組成物を塗布する工程(3a)、レジストパターンをエッチング除去してパターンを反転させる工程(4a)、を含む半導体装置の製造方法であって、
前記有機パターン平坦化用組成物が加水分解性シラン原料の加水分解縮合物を含むポリシロキサンと溶媒とを含み、上記ポリシロキサンが、Si原子に対し、シラノール基を20モル%以下の割合で含むものであり、上記ポリシロキサンの重量平均分子量が1,000~50,000である、半導体装置の製造方法。 - 上記ポリシロキサンが、上記式(1)で示され、aが1である加水分解性シランを100~50モル%、及び上記式(1)で示され、aが2である加水分解性シランを0~50モル%となる割合で含む加水分解性シラン原料の加水分解縮合物を含む、請求項17に記載の製造方法。
- 上記ポリシロキサンが、上記式(1)で示され、aが1である加水分解性シランを100~50モル%、及び上記式(1)で示され、aが2である加水分解性シランを0~50モル%となる割合で含む加水分解性シラン原料の加水分解縮合物の非アルコールと弱酸又は塩基とによる処理生成物である、請求項18に記載の製造方法。
- 弱酸が4~5の酸解離定数を有する酸である、請求項20に記載の製造方法。
- 上記有機パターンがレジストパターン、ナノインプリントパターン及び有機下層膜パターンの中から選ばれる、請求項16~21のいずれか1項に記載の製造方法。
- 工程(3)の後に、塗膜表面をエッチバックして有機パターン表面を露出する工程(3-1)を含む、請求項16~22のいずれか1項に記載の製造方法。
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