JP5316743B2 - ケイ素含有膜形成用組成物およびケイ素含有絶縁膜の形成方法 - Google Patents
ケイ素含有膜形成用組成物およびケイ素含有絶縁膜の形成方法 Download PDFInfo
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- JP5316743B2 JP5316743B2 JP2008031897A JP2008031897A JP5316743B2 JP 5316743 B2 JP5316743 B2 JP 5316743B2 JP 2008031897 A JP2008031897 A JP 2008031897A JP 2008031897 A JP2008031897 A JP 2008031897A JP 5316743 B2 JP5316743 B2 JP 5316743B2
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- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 title claims abstract description 68
- 229910052710 silicon Inorganic materials 0.000 title claims abstract description 68
- 239000010703 silicon Substances 0.000 title claims abstract description 68
- 239000000203 mixture Substances 0.000 title claims abstract description 37
- 238000000034 method Methods 0.000 title claims abstract description 31
- -1 silane compound Chemical class 0.000 claims abstract description 61
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 20
- 238000005229 chemical vapour deposition Methods 0.000 claims abstract description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 15
- 229910000077 silane Inorganic materials 0.000 claims abstract description 13
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 9
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims abstract description 6
- 125000000962 organic group Chemical group 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 125000001153 fluoro group Chemical group F* 0.000 claims description 11
- 238000010438 heat treatment Methods 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 239000000758 substrate Substances 0.000 claims description 7
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 238000010894 electron beam technology Methods 0.000 claims description 3
- 238000000151 deposition Methods 0.000 claims description 2
- 239000010408 film Substances 0.000 description 119
- 150000001875 compounds Chemical class 0.000 description 22
- 230000015572 biosynthetic process Effects 0.000 description 12
- 239000011229 interlayer Substances 0.000 description 11
- 239000004065 semiconductor Substances 0.000 description 11
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- 239000000126 substance Substances 0.000 description 10
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- 230000000052 comparative effect Effects 0.000 description 8
- 229930195733 hydrocarbon Natural products 0.000 description 8
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- 238000006243 chemical reaction Methods 0.000 description 7
- 238000011156 evaluation Methods 0.000 description 7
- 239000004215 Carbon black (E152) Substances 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 6
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- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
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- 229910052749 magnesium Inorganic materials 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000000623 plasma-assisted chemical vapour deposition Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- OOCUOKHIVGWCTJ-UHFFFAOYSA-N chloromethyl(trimethyl)silane Chemical compound C[Si](C)(C)CCl OOCUOKHIVGWCTJ-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
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- GJEZBVHHZQAEDB-UHFFFAOYSA-N 6-oxabicyclo[3.1.0]hexane Chemical compound C1CCC2OC21 GJEZBVHHZQAEDB-UHFFFAOYSA-N 0.000 description 3
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- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
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- 229960002050 hydrofluoric acid Drugs 0.000 description 3
- 238000007654 immersion Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 3
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 3
- 238000001020 plasma etching Methods 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- 150000004756 silanes Chemical class 0.000 description 3
- YIWGJFPJRAEKMK-UHFFFAOYSA-N 1-(2H-benzotriazol-5-yl)-3-methyl-8-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carbonyl]-1,3,8-triazaspiro[4.5]decane-2,4-dione Chemical compound CN1C(=O)N(c2ccc3n[nH]nc3c2)C2(CCN(CC2)C(=O)c2cnc(NCc3cccc(OC(F)(F)F)c3)nc2)C1=O YIWGJFPJRAEKMK-UHFFFAOYSA-N 0.000 description 2
- WZJUBBHODHNQPW-UHFFFAOYSA-N 2,4,6,8-tetramethyl-1,3,5,7,2$l^{3},4$l^{3},6$l^{3},8$l^{3}-tetraoxatetrasilocane Chemical compound C[Si]1O[Si](C)O[Si](C)O[Si](C)O1 WZJUBBHODHNQPW-UHFFFAOYSA-N 0.000 description 2
- MELPJGOMEMRMPL-UHFFFAOYSA-N 9-oxabicyclo[6.1.0]nonane Chemical compound C1CCCCCC2OC21 MELPJGOMEMRMPL-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CFCDXQFWUHLEBQ-UHFFFAOYSA-N C(C)O[Si](CCO[Si](OC)(OC)OC)(OCC)OCC Chemical compound C(C)O[Si](CCO[Si](OC)(OC)OC)(OCC)OCC CFCDXQFWUHLEBQ-UHFFFAOYSA-N 0.000 description 2
- ATYUKIGQFAGPOB-UHFFFAOYSA-N CCOC(OCC)[SiH2]C[Si](OCC)(OCC)OCC Chemical compound CCOC(OCC)[SiH2]C[Si](OCC)(OCC)OCC ATYUKIGQFAGPOB-UHFFFAOYSA-N 0.000 description 2
- IPTCUHRODGBRMY-UHFFFAOYSA-N CO[Si](CCO[Si](OC)(OC)OC)(OC)OC Chemical compound CO[Si](CCO[Si](OC)(OC)OC)(OC)OC IPTCUHRODGBRMY-UHFFFAOYSA-N 0.000 description 2
- DISYUDZUSOXLEZ-UHFFFAOYSA-N CO[Si](CO[Si](OC)(OC)OC)(OC)OC Chemical compound CO[Si](CO[Si](OC)(OC)OC)(OC)OC DISYUDZUSOXLEZ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 2
- VPLIEAVLKBXZCM-UHFFFAOYSA-N [diethoxy(methyl)silyl]-diethoxy-methylsilane Chemical compound CCO[Si](C)(OCC)[Si](C)(OCC)OCC VPLIEAVLKBXZCM-UHFFFAOYSA-N 0.000 description 2
- JWVHPGDCFVOYMQ-UHFFFAOYSA-N [dimethoxy(methyl)silyl]oxy-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)O[Si](C)(OC)OC JWVHPGDCFVOYMQ-UHFFFAOYSA-N 0.000 description 2
- KCCVBXQGWAXUSD-UHFFFAOYSA-N [dimethoxy(phenyl)silyl]oxy-dimethoxy-phenylsilane Chemical compound C=1C=CC=CC=1[Si](OC)(OC)O[Si](OC)(OC)C1=CC=CC=C1 KCCVBXQGWAXUSD-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 2
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- GAURFLBIDLSLQU-UHFFFAOYSA-N diethoxy(methyl)silicon Chemical compound CCO[Si](C)OCC GAURFLBIDLSLQU-UHFFFAOYSA-N 0.000 description 2
- NYROPPYCYUGLLK-UHFFFAOYSA-N diethoxymethyl(diethoxymethylsilylmethyl)silane Chemical compound CCOC(OCC)[SiH2]C[SiH2]C(OCC)OCC NYROPPYCYUGLLK-UHFFFAOYSA-N 0.000 description 2
- VSYLGGHSEIWGJV-UHFFFAOYSA-N diethyl(dimethoxy)silane Chemical compound CC[Si](CC)(OC)OC VSYLGGHSEIWGJV-UHFFFAOYSA-N 0.000 description 2
- JKCULUIKKVYAPV-UHFFFAOYSA-N diethyl-bis(triethylsilyl)silane Chemical compound CC[Si](CC)(CC)[Si](CC)(CC)[Si](CC)(CC)CC JKCULUIKKVYAPV-UHFFFAOYSA-N 0.000 description 2
- JJQZDUKDJDQPMQ-UHFFFAOYSA-N dimethoxy(dimethyl)silane Chemical compound CO[Si](C)(C)OC JJQZDUKDJDQPMQ-UHFFFAOYSA-N 0.000 description 2
- AHUXYBVKTIBBJW-UHFFFAOYSA-N dimethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OC)(OC)C1=CC=CC=C1 AHUXYBVKTIBBJW-UHFFFAOYSA-N 0.000 description 2
- PKTOVQRKCNPVKY-UHFFFAOYSA-N dimethoxy(methyl)silicon Chemical compound CO[Si](C)OC PKTOVQRKCNPVKY-UHFFFAOYSA-N 0.000 description 2
- WWPKQZIHGGRBLB-UHFFFAOYSA-N dimethoxy-bis(trimethoxysilyl)silane Chemical compound CO[Si](OC)(OC)[Si](OC)(OC)[Si](OC)(OC)OC WWPKQZIHGGRBLB-UHFFFAOYSA-N 0.000 description 2
- ZPILIIPBPKDNTR-UHFFFAOYSA-N dimethoxymethyl(dimethoxymethylsilylmethyl)silane Chemical compound COC(OC)[SiH2]C[SiH2]C(OC)OC ZPILIIPBPKDNTR-UHFFFAOYSA-N 0.000 description 2
- AKPOQTZQHIWYJM-UHFFFAOYSA-N dimethoxymethylsilylmethyl(trimethoxy)silane Chemical compound COC(OC)[SiH2]C[Si](OC)(OC)OC AKPOQTZQHIWYJM-UHFFFAOYSA-N 0.000 description 2
- DDIMPUQNMJIVKL-UHFFFAOYSA-N dimethyl-bis(trimethylsilyl)silane Chemical compound C[Si](C)(C)[Si](C)(C)[Si](C)(C)C DDIMPUQNMJIVKL-UHFFFAOYSA-N 0.000 description 2
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- GPCIFOPQYZCLTR-UHFFFAOYSA-N ethoxy-[ethoxy(diphenyl)silyl]-diphenylsilane Chemical compound C=1C=CC=CC=1[Si]([Si](OCC)(C=1C=CC=CC=1)C=1C=CC=CC=1)(OCC)C1=CC=CC=C1 GPCIFOPQYZCLTR-UHFFFAOYSA-N 0.000 description 2
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- 159000000003 magnesium salts Chemical class 0.000 description 2
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- CEXMDIMEZILRLH-UHFFFAOYSA-N methoxy-[methoxy(diphenyl)silyl]-diphenylsilane Chemical compound C=1C=CC=CC=1[Si]([Si](OC)(C=1C=CC=CC=1)C=1C=CC=CC=1)(OC)C1=CC=CC=C1 CEXMDIMEZILRLH-UHFFFAOYSA-N 0.000 description 2
- CDHRQJOOOVAAFQ-UHFFFAOYSA-N methoxy-[methoxy(diphenyl)silyl]oxy-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(OC)O[Si](OC)(C=1C=CC=CC=1)C1=CC=CC=C1 CDHRQJOOOVAAFQ-UHFFFAOYSA-N 0.000 description 2
- ITQHQEHPMRUBPF-UHFFFAOYSA-N methoxy-bis[methoxy(dimethyl)silyl]-methylsilane Chemical compound CO[Si](C)(C)[Si](C)(OC)[Si](C)(C)OC ITQHQEHPMRUBPF-UHFFFAOYSA-N 0.000 description 2
- HLXDKGBELJJMHR-UHFFFAOYSA-N methyl-tri(propan-2-yloxy)silane Chemical compound CC(C)O[Si](C)(OC(C)C)OC(C)C HLXDKGBELJJMHR-UHFFFAOYSA-N 0.000 description 2
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- 125000001424 substituent group Chemical group 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
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 2
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- YYJNCOSWWOMZHX-UHFFFAOYSA-N triethoxy-(4-triethoxysilylphenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=C([Si](OCC)(OCC)OCC)C=C1 YYJNCOSWWOMZHX-UHFFFAOYSA-N 0.000 description 2
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- LMQGXNPPTQOGDG-UHFFFAOYSA-N trimethoxy(trimethoxysilyl)silane Chemical compound CO[Si](OC)(OC)[Si](OC)(OC)OC LMQGXNPPTQOGDG-UHFFFAOYSA-N 0.000 description 2
- DJYGUVIGOGFJOF-UHFFFAOYSA-N trimethoxy(trimethoxysilylmethyl)silane Chemical compound CO[Si](OC)(OC)C[Si](OC)(OC)OC DJYGUVIGOGFJOF-UHFFFAOYSA-N 0.000 description 2
- KNYWDHFOQZZIDQ-UHFFFAOYSA-N trimethoxy-(2-trimethoxysilylphenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1[Si](OC)(OC)OC KNYWDHFOQZZIDQ-UHFFFAOYSA-N 0.000 description 2
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- NBAPKCYEEBMZDW-UHFFFAOYSA-N tripropoxy-(2-tripropoxysilylphenyl)silane Chemical compound CCCO[Si](OCCC)(OCCC)C1=CC=CC=C1[Si](OCCC)(OCCC)OCCC NBAPKCYEEBMZDW-UHFFFAOYSA-N 0.000 description 1
- YMAKWPVRMIUZBP-UHFFFAOYSA-N tripropoxy-(3-tripropoxysilylphenyl)silane Chemical compound CCCO[Si](OCCC)(OCCC)C1=CC=CC([Si](OCCC)(OCCC)OCCC)=C1 YMAKWPVRMIUZBP-UHFFFAOYSA-N 0.000 description 1
- FOUOZDXPXSKVEL-UHFFFAOYSA-N tripropoxy-(4-tripropoxysilylphenyl)silane Chemical compound CCCO[Si](OCCC)(OCCC)C1=CC=C([Si](OCCC)(OCCC)OCCC)C=C1 FOUOZDXPXSKVEL-UHFFFAOYSA-N 0.000 description 1
- OZWKZRFXJPGDFM-UHFFFAOYSA-N tripropoxysilane Chemical compound CCCO[SiH](OCCC)OCCC OZWKZRFXJPGDFM-UHFFFAOYSA-N 0.000 description 1
- ZZEMYLNHCSTIPH-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]-[2-[tris[(2-methylpropan-2-yl)oxy]silyl]phenyl]silane Chemical compound CC(C)(C)O[Si](OC(C)(C)C)(OC(C)(C)C)C1=CC=CC=C1[Si](OC(C)(C)C)(OC(C)(C)C)OC(C)(C)C ZZEMYLNHCSTIPH-UHFFFAOYSA-N 0.000 description 1
- NNKMRNUOGTXRCM-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]-[3-[tris[(2-methylpropan-2-yl)oxy]silyl]phenyl]silane Chemical compound CC(C)(C)O[Si](OC(C)(C)C)(OC(C)(C)C)C1=CC=CC([Si](OC(C)(C)C)(OC(C)(C)C)OC(C)(C)C)=C1 NNKMRNUOGTXRCM-UHFFFAOYSA-N 0.000 description 1
- PITXUFPLSLHXRV-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]-[4-[tris[(2-methylpropan-2-yl)oxy]silyl]phenyl]silane Chemical compound CC(C)(C)O[Si](OC(C)(C)C)(OC(C)(C)C)C1=CC=C([Si](OC(C)(C)C)(OC(C)(C)C)OC(C)(C)C)C=C1 PITXUFPLSLHXRV-UHFFFAOYSA-N 0.000 description 1
- QJJZQRNPNLTSNS-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]-[tris[(2-methylpropan-2-yl)oxy]silylmethyl]silane Chemical compound CC(C)(C)O[Si](OC(C)(C)C)(OC(C)(C)C)C[Si](OC(C)(C)C)(OC(C)(C)C)OC(C)(C)C QJJZQRNPNLTSNS-UHFFFAOYSA-N 0.000 description 1
- KGOOITCIBGXHJO-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]-phenylsilane Chemical compound CC(C)(C)O[Si](OC(C)(C)C)(OC(C)(C)C)C1=CC=CC=C1 KGOOITCIBGXHJO-UHFFFAOYSA-N 0.000 description 1
- MJIHPVLPZKWFBL-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]-propan-2-ylsilane Chemical compound CC(C)(C)O[Si](C(C)C)(OC(C)(C)C)OC(C)(C)C MJIHPVLPZKWFBL-UHFFFAOYSA-N 0.000 description 1
- DIZPPYBTFPZSGK-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]-propylsilane Chemical compound CCC[Si](OC(C)(C)C)(OC(C)(C)C)OC(C)(C)C DIZPPYBTFPZSGK-UHFFFAOYSA-N 0.000 description 1
- QYEFZDZJOXNQNW-UHFFFAOYSA-N tritert-butyl(ethoxy)silane Chemical compound CCO[Si](C(C)(C)C)(C(C)(C)C)C(C)(C)C QYEFZDZJOXNQNW-UHFFFAOYSA-N 0.000 description 1
- IEVQSSVQJPNPJB-UHFFFAOYSA-N tritert-butyl(methoxy)silane Chemical compound CO[Si](C(C)(C)C)(C(C)(C)C)C(C)(C)C IEVQSSVQJPNPJB-UHFFFAOYSA-N 0.000 description 1
- RBTCNDHCLUCWFZ-UHFFFAOYSA-N tritert-butyl(phenoxy)silane Chemical compound CC(C)(C)[Si](C(C)(C)C)(C(C)(C)C)OC1=CC=CC=C1 RBTCNDHCLUCWFZ-UHFFFAOYSA-N 0.000 description 1
- QKNKVHOKXSOSDR-UHFFFAOYSA-N tritert-butyl(propan-2-yloxy)silane Chemical compound CC(C)O[Si](C(C)(C)C)(C(C)(C)C)C(C)(C)C QKNKVHOKXSOSDR-UHFFFAOYSA-N 0.000 description 1
- BCURBAMVEGJCFL-UHFFFAOYSA-N tritert-butyl(propoxy)silane Chemical compound CCCO[Si](C(C)(C)C)(C(C)(C)C)C(C)(C)C BCURBAMVEGJCFL-UHFFFAOYSA-N 0.000 description 1
- KWMXETUDGREVLD-UHFFFAOYSA-N tritert-butyl-[(2-methylpropan-2-yl)oxy]silane Chemical compound CC(C)(C)O[Si](C(C)(C)C)(C(C)(C)C)C(C)(C)C KWMXETUDGREVLD-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 239000006200 vaporizer Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
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- Compositions Of Macromolecular Compounds (AREA)
- Silicon Polymers (AREA)
- Formation Of Insulating Films (AREA)
Description
下記一般式(1)で表されるシラン化合物と、
下記一般式(2)ないし(4)のうちから選ばれた少なくとも1種のシラン化合物と、を含む。
(式中、R1〜R4は、同一または異なり、水素原子、炭素数1〜4のアルキル基、ビニル基、フェニル基を示し、R5は炭素数1〜4のアルキル基、アセチル基、フェニル基を示し、nは1〜3の整数を示し、mは1〜2の整数を示す。)
R6 aSi(OR7)4−a ・・・・・(2)
(式中、R6は同一または異なり水素原子、フッ素原子または1価の有機基を示し、R7は同一または異なり、1価の有機基を示し、aは0〜3の整数を示す。)
R8 b(R9O)3−bSi−(R12)d−Oe−Si(OR10)3−cR11 c
・・・(3)
(式中、R8〜R11は同一または異なり、それぞれ水素原子、フッ素原子、1価の有機基を示し、bおよびcは同一または異なり、それぞれ0〜3の数を示し、R12はフェニレン基または−(CH2)m−で表される基(ここで、mは1〜6の整数である)を示し、dならびにeは0または1を示す。)
(式中、R13およびR14は同一または異なり、水素原子、フッ素原子、または1価の有機基より選ばれる基を示し、R15は酸素原子、フェニレン基または−(CH2)n−で表される基(ここで、nは1〜6の整数である)を示し、fは0〜2の整数を,gは0または1を、hは2〜30の数を示す。)
上記ケイ素含有膜形成用組成物は、空孔形成剤として有機分子をさらに含むことができる。
上記ケイ素含有膜形成用組成物を化学気相成長法により基板に堆積させる工程を含む。
加熱、電子線照射、紫外線照射、および酸素プラズマから選ばれる少なくとも1種によって、前記堆積膜の硬化処理を行う工程、をさらに含む。
上記一般式(2)ないし(4)のうちから選ばれた少なくとも1種のシラン化合物とを含
むことにより、高集積化および多層化が望まれている半導体素子などにおいて好適に用いることができ、化学的に安定でありながら化学的気相成長法に最適であり、機械的強度に優れ、低比誘電率でかつ吸湿性が低く、加工耐性が高い絶縁膜を形成するために用いることができる。
本発明の一実施形態に係るケイ素含有膜形成用組成物は、下記一般式(1)で表される有機シラン化合物(以下、「(I)成分」ともいう。)と、下記一般式(2)ないし(4)のうちから選ばれた少なくとも1種のシラン化合物(以下、「(II)成分」ともいう。
)と、を含む。また、ケイ素含有膜形成用組成物は、空孔形成剤としての有機分子(以下、「(III)成分」ともいう。)をさらに含んでもよい。
(式中、R1〜R4は、同一または異なり、水素原子、炭素数1〜4のアルキル基、ビニル基、フェニル基を示し、R5は炭素数1〜4のアルキル基、アセチル基、フェニル基を示し、nは1〜3の整数を示し、mは1〜2の整数を示す。)
R6 aSi(OR7)4−a ・・・・・(2)
(式中、R6は同一または異なり水素原子、フッ素原子または1価の有機基を示し、R7は同一または異なり、1価の有機基を示し、aは0〜3の整数を示す。)
R8 b(R9O)3−bSi−(R12)d−Oe−Si(OR10)3−cR11 c
・・・(3)
(式中、R8〜R11は同一または異なり、それぞれ水素原子、フッ素原子、1価の有機基を示し、bおよびcは同一または異なり、それぞれ0〜3の数を示し、R12はフェニレン基または−(CH2)m−で表される基(ここで、mは1〜6の整数である)を示し、dならびにeは0または1を示す。)
(式中、R13およびR14は同一または異なり、水素原子、フッ素原子、または1価の有機基より選ばれる基を示し、R15は酸素原子、フェニレン基または−(CH2)n−で表される基(ここで、nは1〜6の整数である)を示し、fは0〜2の整数を,gは0または1を、hは2〜30の数を示す。)
本実施の形態に係るケイ素含有膜形成用組成物において、(I)成分と(II)成分のモル比は、(I)成分および(II)成分の合計を100モル%としたとき、(I)成分が10モル%〜90モル%であり、15モル%〜85モル%であることがより好ましい。
1.1.1.(I)成分の構造
本実施の形態に係る(I)成分としての有機シラン化合物は、上記一般式(1)で示される。
上記一般式(1)で表される有機シラン化合物の製造方法は、特に限定されるものではないが、例えば、下記一般式(5)で表される有機シラン化合物と下記一般式(6)で示される有機シラン化合物とを金属存在下でカップリング反応させる方法を挙げることができる。金属としては、通常マグネシウムが用いられる。
(式中、R4は、同一または異なり、水素原子、炭素数1〜4のアルキル基、ビニル基、フェニル基を示し、R5は炭素数1〜4のアルキル基、アセチル基、フェニル基を示し、Yはハロゲン原子、水素原子、アルコキシ基を示し、mは1〜2の整数を示す。)
上記一般式(5)および(6)において、R1〜R5で示される炭素数1〜4のアルキル基としては、上記一般式(1)においてR1〜R5で示される炭素数1〜4のアルキル基として例示したものが挙げられ、X,Yで示されるハロゲン原子としては、例えば、臭素原子、塩素原子が挙げられ、Yで示されるアルコキシ基としては、上記一般式(1)において−OR5で示されるアルコキシ基として例示されるものが挙げられる。
本実施の形態に係る(II)成分としてのシラン化合物は、上記一般式(2)で示される化合物1、上記一般式(3)で示される化合物2、および上記一般式(4)で示される化合物3のうちから選ばれた少なくとも1種である。化合物1〜3については、1種または2種以上を同時に使用してもよい。
上記一般式(2)において、R6,R7で示される1価の有機基としては、アルキル基、アルケニル基、アリール基、アリル基、グリシジル基等を挙げることができる。なかでも、R6,R7で表される1価の有機基は、アルキル基またはフェニル基であることが好ましい。
トリフェノキシシラン、メチルトリメトキシシラン、メチルトリエトキシシラン、メチルトリ−n−プロポキシシラン、メチルトリイソプロポキシシラン、メチルトリ−n−ブトキシシラン、メチルトリ−sec−ブトキシシラン、メチルトリ−tert−ブトキシシ
ラン、メチルトリフェノキシシラン、エチルトリメトキシシラン、エチルトリエトキシシラン、エチルトリ−n−プロポキシシラン、エチルトリイソプロポキシシラン、エチルトリ−n−ブトキシシラン、エチルトリ−sec−ブトキシシラン、エチルトリ−tert−ブトキシシラン、エチルトリフェノキシシラン、n−プロピルトリメトキシシラン、n−プロピルトリエトキシシラン、n−プロピルトリ−n−プロポキシシラン、n−プロピルトリイソプロポキシシラン、n−プロピルトリ−n−ブトキシシラン、n−プロピルトリ−sec−ブトキシシラン、n−プロピルトリ−tert−ブトキシシラン、n−プロピルトリフェノキシシラン、イソプロピルトリメトキシシラン、イソプロピルトリエトキシシラン、イソプロピルトリ−n−プロポキシシラン、イソプロピルトリイソプロポキシシラン、イソプロピルトリ−n−ブトキシシラン、イソプロピルトリ−sec−ブトキシシラン、イソプロピルトリ−tert−ブトキシシラン、イソプロピルトリフェノキシシラン、n−ブチルトリメトキシシラン、n−ブチルトリエトキシシラン、n−ブチルトリ−n−プロポキシシラン、n−ブチルトリイソプロポキシシラン、n−ブチルトリ−n−ブトキシシラン、n−ブチルトリ−sec−ブトキシシラン、n−ブチルトリ−tert−ブトキシシラン、n−ブチルトリフェノキシシラン、sec−ブチルトリメトキシシラン、sec−ブチルイソトリエトキシシラン、sec−ブチルトリ−n−プロポキシシラン、sec−ブチルトリイソプロポキシシラン、sec−ブチルトリ−n−ブトキシシラン、sec−ブチルトリ−sec−ブトキシシラン、sec−ブチルトリ−tert−ブトキシシラン、sec−ブチルトリフェノキシシラン、tert−ブチルトリメトキシシラン、tert−ブチルトリエトキシシラン、tert−ブチルト−n−プロポキシシラン、tert−ブチルトリイソプロポキシシラン、tert−ブチルトリ−n−ブトキシシラン、tert−ブチルトリ−sec−ブトキシシラン、tert−ブチルトリ−tert−ブトキシシラン、tert−ブチルトリフェノキシシラン、フェニルトリメトキシシラン、フェニルトリエトキシシラン、フェニルトリ−n−プロポキシシラン、フェニルトリイソプロポキシシラン、フェニルトリ−n−ブトキシシラン、フェニルトリ−sec−ブトキシシラン、フェニルトリ−tert−ブトキシシラン、フェニルトリフェノキシシランなどを挙げることができ、特に好ましい化合物としては、トリメトキシシラン、トリエトキシシラン、メチルトリメトキシシラン、メチルトリエトキシシラン、メチルトリ−n−プロポキシシラン、メチルトリ−iso−プロポキシシラン、エチルトリメトキシシラン、エチルトリエトキシシラン、フェニルトリメトキシシラン、フェニルトリエトキシシランが挙げられる。
ジ−n−ブチルジ−n−ブトキシシラン、ジ−n−ブチルジ−sec−ブトキシシラン、ジ−n−ブチルジ−tert−ブトキシシラン、ジ−n−ブチルジ−フェノキシシラン、ジ−sec−ブチルジメトキシシラン、ジ−sec−ブチルジエトキシシラン、ジ−sec−ブチルジ−n−プロポキシシラン、ジ−sec−ブチルジイソプロポキシシラン、ジ−sec−ブチルジ−n−ブトキシシラン、ジ−sec−ブチルジ−sec−ブトキシシラン、ジ−sec−ブチルジ−tert−ブトキシシラン、ジ−sec−ブチルジ−フェノキシシラン、ジ−tert−ブチルジメトキシシラン、ジ−tert−ブチルジエトキシシラン、ジ−tert−ブチルジ−n−プロポキシシラン、ジ−tert−ブチルジイソプロポキシシラン、ジ−tert−ブチルジ−n−ブトキシシラン、ジ−tert−ブチルジ−sec−ブトキシシラン、ジ−tert−ブチルジ−tert−ブトキシシラン、ジ−tert−ブチルジ−フェノキシシラン、ジフェニルジメトキシシラン、ジフェニルジエトキシシラン、ジフェニルジ−n−プロポキシシラン、ジフェニルジイソプロポキシシラン、ジフェニルジ−n−ブトキシシラン、ジフェニルジ−sec−ブトキシシラン、ジフェニルジ−tert−ブトキシシラン、ジフェニルジフェノキシシラン挙げることができ、特に好ましい化合物としては、メチルジメトキシシラン、メチルジエトキシシラン、ジメチルジメトキシシラン、ジメチルジエトキシシラン、ジエチルジメトキシシラン、ジエチルジエトキシシラン、ジフェニルジメトキシシラン、ジフェニルジエトキシシラン等が挙げられる。
フェニル−iso−プロポキシシラン、トリフェニル−n−ブトキシシラン、トリフェニル−sec−ブトキシシラン、トリフェニル−tert−ブトキシシラン、トリフェニルフェノキシシランなどが挙げることができ、特に好ましい化合物としてはジメチルメトキシシラン、ジメチルエトキシシラン、トリメチルメトキシシラン、トリメチルエトキシシラン、トリメチル-n-プロポキシシラン、トリエチルメトキシシラン、トリエチルエトキ
シシラン、トリエチル−n−プロポキシシラン、トリフェニルメトキシシラン、トリフェニル−エトキシシラン、トリフェニル−n−プロポキシシラン等が挙げられる。
上記一般式(3)において、R8〜R11で示される1価の有機基としては、上記一般式(2)のR6,R7として例示したものと同様の基を挙げることができる。
ェニルジシラン等を好ましい例として挙げることができる。
エタン、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、1−(ジメトキシメチルシリル)−2−(トリメトキシシリル)エタン、1−(ジエトキシメチルシリル)−2−(トリエトキシシリル)エタン、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、1,2−ビス(ジメトキシメチルシリル)エタン、1,2−ビス(ジエトキシメチルシリル)エタン、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、1,3−ビス(トリメトキシシリル)ベンゼン、1,3−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)ベンゼン等を好ましい例として挙げることができる。
キシ)エタン、1−(トリエトキシシリル)−1−(トリメトキシシロキシ)メタン、1−(トリエトキシシリル)−2−(トリメトキシシロキシ)エタンを好ましい例としてあげることができる。
本実施の形態に係る化合物3は、上記一般式(4)で示される繰り返し構造を有するオリゴマーであり、環状構造を有していてもよい。
上記ケイ素含有膜形成用組成物は、空孔形成剤として有機分子をさらに含むことができる。
オキサビシクロ化合物としては、例えば、6−オキサビシクロ[3.1.0]ヘキサン(シクロペンテンオキサイド)、7−オキサビシクロ[4.1.0]ヘプタン(シクロヘキセンオキサイド)、9−オキサビシクロ[6.1.0]ノナン(シクロオクテンオキサイド)、7−オキサビシクロ[2.2.1]ヘプタン(1,4−エポキシシクロヘキサン)が挙げられる。
多環性炭化水素は、炭素数が6〜12であることが好ましく、例えば、2,5−ノルボマジエン(ビシクロ[2.2.1]ヘプタ−2,5−ジエン)、ノルボミレン 2,5−ノルボルナジエン(ビシクロ[2.2.1]ヘプタ−2,5−ジエン)、ノルボルナン(ビシクロ[2.2.1]ヘプタン)、トリシクロ[3.2.1.0]オクタン、トリシクロ[3.2.2.0]ノナン、スピロ[3.4]オクタン、スピロ[4.5]ノナン、スピロ[5.6]デカンなどの結合環炭化水素が挙げられる。
単環性炭化水素としては、例えば、シクロペンタン、シクロヘキサンなどの炭素数が5〜12の脂環式炭化水素や、ベンゼン、トルエン、キシレン(o−キシレン、m−キシレン、n−キシレン)などの炭素数が6〜12の芳香族炭化水素が挙げられる。
本発明の一実施形態に係るケイ素含有絶縁膜の形成方法は、化学気相成長法(CVD法
)によって行う。特にプラズマ励起CVD法(PECVD法)により行うことが好ましい。PECVD法装置において、上記一般式(1)で表される有機シラン化合物、上記一般式(2)ないし(4)のうちから選ばれた少なくとも1種のシラン化合物と、必要に応じて空孔形成剤を含む、ケイ素含有膜形成用組成物を気化器により気化させて、成膜チャンバー内に導入し、高周波電源により成膜チャンバー内の電極に印加し、プラズマを発生させることにより、成膜チャンバー内の基材にプラズマCVD膜を形成することができる。
本発明の一実施形態に係るケイ素含有絶縁膜は上記形成方法により得ることができる。
適に用いることができる。
以下、本発明を、実施例を挙げてさらに具体的に説明する。本発明は以下の実施例に限定されるものではない。なお、実施例および比較例中の「部」および「%」は、特記しない限り、それぞれ重量部および重量%であることを示している。
各種の評価は、次のようにして行った。
8インチシリコンウエハ上に、PECVD法により後述する条件によりケイ素含有絶縁膜を形成した。得られた膜に、蒸着法によりアルミニウム電極パターンを形成し、比誘電率測定用サンプルを作成した。該サンプルについて、周波数100kHzの周波数で、横河・ヒューレットパッカード(株)製、HP16451B電極およびHP4284AプレシジョンLCRメータを用いてCV法により当該絶縁膜の比誘電率を測定した。Δkは、24℃、40%RHの雰囲気で測定した比誘電率(k@RT)と、200℃、乾燥窒素雰囲気下で測定した比誘電率(k@200℃)との差(Δk=k@RT−k@200℃)である。かかるΔkにより、主に、膜の吸湿による比誘電率の上昇分を評価することができる。通常、Δkが0.15以上であると、吸水性の高いケイ素含有絶縁膜であるといえる。
MTS社製超微少硬度計(Nanoindentator XP)にバーコビッチ型圧子
を取り付け、得られた絶縁膜のユニバーサル硬度を求めた。また、弾性率は連続剛性測定法により測定した。
ケイ素含有絶縁膜が形成された8インチウエハを、室温で0.2%の希フッ酸水溶液中に3分間浸漬し、浸漬前後のケイ素含有膜の膜厚変化を観察した。下記に定義する残膜率が99%以上であれば、薬液耐性が良好であると判断する。
A:残膜率が99%以上である。
4.2.1.(I)成分の合成例1
冷却コンデンサーおよび滴下ロートを備えた3つ口フラスコを50℃で減圧乾燥した後、窒素充填した。次いで、フラスコ内にマグネシウム20gおよびTHF500mlを加え、室温で撹拌しながら(クロロメチル)トリメチルシラン25gを加えた。しばらく撹拌し、発熱を確認した後、滴下ロートから(クロロメチル)トリメチルシラン55gを30分かけて加えた。滴下終了後、液温が室温に戻ったのを確認した後、フラスコにTHF250mlおよびメチルトリメトキシシラン237gの混合液を加え、続いて、70℃で6時間加熱還流することにより、反応を完結させた。反応液を室温まで冷却した後、生成したマグネシウム塩および未反応のマグネシウムを濾別し、濾液を分留することで、[(トリメチルシリル)メチル]メチルジメトキシシラン75g(収率70%)を得た(GC法で確認)。得られた(I)成分を化合物Aとする。
冷却コンデンサーおよび滴下ロートを備えた3つ口フラスコを50℃で減圧乾燥した後、窒素充填した。次いで、フラスコ内にマグネシウム20gおよびTHF500mlを加え、室温で撹拌しながら(クロロメチル)トリメチルシラン25gを加えた。しばらく撹拌し、発熱を確認した後、滴下ロートから(クロロメチル)トリメチルシラン55gを30分かけて加えた。滴下終了後、液温が室温に戻ったのを確認した後、フラスコにTHF250mlおよびビニルトリメトキシシラン258gの混合液を加え、続いて、70℃で6時間加熱還流することにより、反応を完結させた。反応液を室温まで冷却した後、生成したマグネシウム塩および未反応のマグネシウムを濾別し、濾液を分留することで、[(トリメチルシリル)メチル]ビニルジメトキシシラン80g(収率65%)を得た(GC法で確認)。得られた(I)成分を化合物Bとする。
合成例1,2で得られた化合物AまたはBと、表1に示す(II)成分とを、表1に示すモル比で混合してケイ素含有膜形成用組成物を調製した。また実施例10および11では、(I)成分および(II)成分に加えて、(III)成分を混合してケイ素含有膜形成用組
成物を調製した。(I)成分および(II)成分の総重量を100としたときの(III)成
分の重量を表1に示す。
実施例1〜11および比較例1〜3で製造したケイ素含有膜形成用組成物の各々を用いて、ケイ素含有絶縁膜を形成した。具体的には、サムコ社製プラズマCVD装置PD−220Nを用い、ケイ素含有膜形成用組成物のガス流量25sccm、Arのガス流量3sccm、RF電力250W、基板温度380℃、反応圧力10Torrの条件でプラズマCVD法により、シリコン基板上にケイ素含有絶縁膜0.5μmを成膜した。
それぞれの絶縁膜について、「4.1.評価方法」に記載の評価を行った。評価結果を表2に示す。
(III)成分を加えない絶縁膜に比べて、比誘電率および吸湿性を示す指標であるΔkが
低く、薬液耐性においても優れていた。
実施例1−4ならびに比較例1については、4.3で示すプラズマCVD成膜後、酸素分圧0.01kPaのチャンバー内にて、ホットプレート上で塗膜を400℃で加熱しながら、紫外線を照射した。紫外線源は、波長250nm以下の波長を含む白色紫外線を用いた。なお、この紫外線は白色紫外光のため、有効な方法で照度の測定は行なえなかった。
Claims (4)
- 下記一般式(1)で表されるシラン化合物と、
下記一般式(2)ないし(4)のうちから選ばれた少なくとも1種のシラン化合物と、を含む、化学気相成長法に用いられるケイ素含有膜形成用組成物。
(式中、R1〜R4は、同一または異なり、水素原子、炭素数1〜4のアルキル基、ビニル基、フェニル基を示し、R5は炭素数1〜4のアルキル基、アセチル基、フェニル基を示し、nは1〜3の整数を示し、mは1〜2の整数を示す。)
R6 aSi(OR7)4−a ・・・・・(2)
(式中、R6は同一または異なり水素原子、フッ素原子または1価の有機基を示し、R7は同一または異なり、1価の有機基を示し、aは0〜3の整数を示す。)
R8 b(R9O)3−bSi−(R12)d−Oe−Si(OR10)3−cR11 c
・・・(3)
(式中、R8〜R11は同一または異なり、それぞれ水素原子、フッ素原子、1価の有機基を示し、bおよびcは同一または異なり、それぞれ0〜3の数を示し、R12はフェニレン基または−(CH2)m−で表される基(ここで、mは1〜6の整数である)を示し、dならびにeは0または1を示す。)
(式中、R13およびR14は同一または異なり、水素原子、フッ素原子、または1価の有機基より選ばれる基を示し、R15は酸素原子、フェニレン基または−(CH2)n−で表される基(ここで、nは1〜6の整数である)を示し、fは0〜2の整数を,gは0または1を、hは2〜30の数を示す。) - 空孔形成剤として有機分子をさらに含む、請求項1に記載の化学気相成長法に用いられるケイ素含有膜形成用組成物。
- 請求項1または2に記載のケイ素含有膜形成用組成物を化学気相成長法により基板に堆積させる工程を含む、ケイ素含有絶縁膜の形成方法。
- 加熱、電子線照射、紫外線照射、および酸素プラズマから選ばれる少なくとも1種によって、前記基板に堆積させた堆積膜の硬化処理を行う工程、をさらに含む、請求項3に記載のケイ素含有絶縁膜の形成方法。
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