JP2005350653A - 有機シリカ系膜の形成方法、有機シリカ系膜、配線構造体、半導体装置、および膜形成用組成物 - Google Patents
有機シリカ系膜の形成方法、有機シリカ系膜、配線構造体、半導体装置、および膜形成用組成物 Download PDFInfo
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- JP2005350653A JP2005350653A JP2005050590A JP2005050590A JP2005350653A JP 2005350653 A JP2005350653 A JP 2005350653A JP 2005050590 A JP2005050590 A JP 2005050590A JP 2005050590 A JP2005050590 A JP 2005050590A JP 2005350653 A JP2005350653 A JP 2005350653A
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- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 5
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- 125000005372 silanol group Chemical group 0.000 description 5
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 4
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- 229940022663 acetate Drugs 0.000 description 4
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- SGZJOYFOVHWDFY-UHFFFAOYSA-N tri(butan-2-yloxy)-[3-tri(butan-2-yloxy)silylphenyl]silane Chemical compound CCC(C)O[Si](OC(C)CC)(OC(C)CC)C1=CC=CC([Si](OC(C)CC)(OC(C)CC)OC(C)CC)=C1 SGZJOYFOVHWDFY-UHFFFAOYSA-N 0.000 description 1
- OHGMZEITXQWDLR-UHFFFAOYSA-N tri(butan-2-yloxy)-[4-tri(butan-2-yloxy)silylphenyl]silane Chemical compound CCC(C)O[Si](OC(C)CC)(OC(C)CC)C1=CC=C([Si](OC(C)CC)(OC(C)CC)OC(C)CC)C=C1 OHGMZEITXQWDLR-UHFFFAOYSA-N 0.000 description 1
- IKCSBNRFPJTRMT-UHFFFAOYSA-N tri(butan-2-yloxy)-[tri(butan-2-yloxy)silylmethyl]silane Chemical compound CCC(C)O[Si](OC(C)CC)(OC(C)CC)C[Si](OC(C)CC)(OC(C)CC)OC(C)CC IKCSBNRFPJTRMT-UHFFFAOYSA-N 0.000 description 1
- HKALKJRBIYJXJT-UHFFFAOYSA-N tri(butan-2-yloxy)-butylsilane Chemical compound CCCC[Si](OC(C)CC)(OC(C)CC)OC(C)CC HKALKJRBIYJXJT-UHFFFAOYSA-N 0.000 description 1
- SGHZCASSRKVVCL-UHFFFAOYSA-N tri(butan-2-yloxy)-ethylsilane Chemical compound CCC(C)O[Si](CC)(OC(C)CC)OC(C)CC SGHZCASSRKVVCL-UHFFFAOYSA-N 0.000 description 1
- RJNDDRZGJNVASH-UHFFFAOYSA-N tri(butan-2-yloxy)-methylsilane Chemical compound CCC(C)O[Si](C)(OC(C)CC)OC(C)CC RJNDDRZGJNVASH-UHFFFAOYSA-N 0.000 description 1
- PCDRXIBYKFIRQR-UHFFFAOYSA-N tri(butan-2-yloxy)-phenylsilane Chemical compound CCC(C)O[Si](OC(C)CC)(OC(C)CC)C1=CC=CC=C1 PCDRXIBYKFIRQR-UHFFFAOYSA-N 0.000 description 1
- ZARIZDBUWOPYMT-UHFFFAOYSA-N tri(butan-2-yloxy)-propylsilane Chemical compound CCC(C)O[Si](CCC)(OC(C)CC)OC(C)CC ZARIZDBUWOPYMT-UHFFFAOYSA-N 0.000 description 1
- JKJUOACCVYNCDI-UHFFFAOYSA-N tri(butan-2-yloxy)-tert-butylsilane Chemical compound CCC(C)O[Si](OC(C)CC)(OC(C)CC)C(C)(C)C JKJUOACCVYNCDI-UHFFFAOYSA-N 0.000 description 1
- COKLPZSYWJNYBJ-UHFFFAOYSA-N tri(butan-2-yloxy)silane Chemical compound CCC(C)O[SiH](OC(C)CC)OC(C)CC COKLPZSYWJNYBJ-UHFFFAOYSA-N 0.000 description 1
- MQVCTPXBBSKLFS-UHFFFAOYSA-N tri(propan-2-yloxy)-propylsilane Chemical compound CCC[Si](OC(C)C)(OC(C)C)OC(C)C MQVCTPXBBSKLFS-UHFFFAOYSA-N 0.000 description 1
- JGABXROLARSPEN-UHFFFAOYSA-N tri(propan-2-yloxy)silane Chemical compound CC(C)O[SiH](OC(C)C)OC(C)C JGABXROLARSPEN-UHFFFAOYSA-N 0.000 description 1
- DGTSXRWJKSHSCG-UHFFFAOYSA-N tribromo(1-tribromosilylethyl)silane Chemical compound Br[Si](Br)(Br)C(C)[Si](Br)(Br)Br DGTSXRWJKSHSCG-UHFFFAOYSA-N 0.000 description 1
- PFWMXXGPKFIEAA-UHFFFAOYSA-N tribromo(2-phenylethyl)silane Chemical compound Br[Si](Br)(Br)CCC1=CC=CC=C1 PFWMXXGPKFIEAA-UHFFFAOYSA-N 0.000 description 1
- HCSBZSDRJAJWHR-UHFFFAOYSA-N tribromo(butyl)silane Chemical compound CCCC[Si](Br)(Br)Br HCSBZSDRJAJWHR-UHFFFAOYSA-N 0.000 description 1
- OABHNYSMYGIZRF-UHFFFAOYSA-N tribromo(cyclohexyl)silane Chemical compound Br[Si](Br)(Br)C1CCCCC1 OABHNYSMYGIZRF-UHFFFAOYSA-N 0.000 description 1
- BZAROSBWJASVBU-UHFFFAOYSA-N tribromo(ethenyl)silane Chemical compound Br[Si](Br)(Br)C=C BZAROSBWJASVBU-UHFFFAOYSA-N 0.000 description 1
- KVENDAGPVNAYLY-UHFFFAOYSA-N tribromo(ethyl)silane Chemical compound CC[Si](Br)(Br)Br KVENDAGPVNAYLY-UHFFFAOYSA-N 0.000 description 1
- KBSUPJLTDMARAI-UHFFFAOYSA-N tribromo(methyl)silane Chemical compound C[Si](Br)(Br)Br KBSUPJLTDMARAI-UHFFFAOYSA-N 0.000 description 1
- HPTIEXHGTPSFDC-UHFFFAOYSA-N tribromo(phenyl)silane Chemical compound Br[Si](Br)(Br)C1=CC=CC=C1 HPTIEXHGTPSFDC-UHFFFAOYSA-N 0.000 description 1
- MHOVTIVXUNGWHW-UHFFFAOYSA-N tribromo(propan-2-yl)silane Chemical compound CC(C)[Si](Br)(Br)Br MHOVTIVXUNGWHW-UHFFFAOYSA-N 0.000 description 1
- RWRKNKVDHIEKHS-UHFFFAOYSA-N tribromo(propyl)silane Chemical compound CCC[Si](Br)(Br)Br RWRKNKVDHIEKHS-UHFFFAOYSA-N 0.000 description 1
- QWBBTCQPNIEDSP-UHFFFAOYSA-N tribromo(tert-butyl)silane Chemical compound CC(C)(C)[Si](Br)(Br)Br QWBBTCQPNIEDSP-UHFFFAOYSA-N 0.000 description 1
- ASWZNPOTXAXUPB-UHFFFAOYSA-N tribromo(tribromosilyl)silane Chemical compound Br[Si](Br)(Br)[Si](Br)(Br)Br ASWZNPOTXAXUPB-UHFFFAOYSA-N 0.000 description 1
- NMWWUBJEHVDRJB-UHFFFAOYSA-N tribromo(tribromosilylmethyl)silane Chemical compound Br[Si](Br)(Br)C[Si](Br)(Br)Br NMWWUBJEHVDRJB-UHFFFAOYSA-N 0.000 description 1
- PWVUSFVRYWVBDM-UHFFFAOYSA-N tribromo(tribromosilyloxy)silane Chemical compound Br[Si](Br)(Br)O[Si](Br)(Br)Br PWVUSFVRYWVBDM-UHFFFAOYSA-N 0.000 description 1
- IBOKZQNMFSHYNQ-UHFFFAOYSA-N tribromosilane Chemical compound Br[SiH](Br)Br IBOKZQNMFSHYNQ-UHFFFAOYSA-N 0.000 description 1
- DEKZKCDJQLBBRA-UHFFFAOYSA-N tributoxy(butyl)silane Chemical compound CCCCO[Si](CCCC)(OCCCC)OCCCC DEKZKCDJQLBBRA-UHFFFAOYSA-N 0.000 description 1
- CQLAZINSWMHWAQ-UHFFFAOYSA-N tributoxy(dibutoxymethylsilylmethyl)silane Chemical compound CCCCOC(OCCCC)[SiH2]C[Si](OCCCC)(OCCCC)OCCCC CQLAZINSWMHWAQ-UHFFFAOYSA-N 0.000 description 1
- GIHPVQDFBJMUAO-UHFFFAOYSA-N tributoxy(ethyl)silane Chemical compound CCCCO[Si](CC)(OCCCC)OCCCC GIHPVQDFBJMUAO-UHFFFAOYSA-N 0.000 description 1
- GYZQBXUDWTVJDF-UHFFFAOYSA-N tributoxy(methyl)silane Chemical compound CCCCO[Si](C)(OCCCC)OCCCC GYZQBXUDWTVJDF-UHFFFAOYSA-N 0.000 description 1
- INUOIYMEJLOQFN-UHFFFAOYSA-N tributoxy(phenyl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)C1=CC=CC=C1 INUOIYMEJLOQFN-UHFFFAOYSA-N 0.000 description 1
- WAAWAIHPWOJHJJ-UHFFFAOYSA-N tributoxy(propyl)silane Chemical compound CCCCO[Si](CCC)(OCCCC)OCCCC WAAWAIHPWOJHJJ-UHFFFAOYSA-N 0.000 description 1
- MVXBTESZGSNIIB-UHFFFAOYSA-N tributoxy(tert-butyl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)C(C)(C)C MVXBTESZGSNIIB-UHFFFAOYSA-N 0.000 description 1
- JXXQPVMVSMWLGZ-UHFFFAOYSA-N tributoxy(tributoxysilylmethyl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)C[Si](OCCCC)(OCCCC)OCCCC JXXQPVMVSMWLGZ-UHFFFAOYSA-N 0.000 description 1
- ZYXLOEAJFSQDQG-UHFFFAOYSA-N tributoxy-(2-tributoxysilylphenyl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)C1=CC=CC=C1[Si](OCCCC)(OCCCC)OCCCC ZYXLOEAJFSQDQG-UHFFFAOYSA-N 0.000 description 1
- UYZUVKDKSJFNIN-UHFFFAOYSA-N tributoxy-(3-tributoxysilylphenyl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)C1=CC=CC([Si](OCCCC)(OCCCC)OCCCC)=C1 UYZUVKDKSJFNIN-UHFFFAOYSA-N 0.000 description 1
- YBNXDKRALACDIA-UHFFFAOYSA-N tributoxy-(4-tributoxysilylphenyl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)C1=CC=C([Si](OCCCC)(OCCCC)OCCCC)C=C1 YBNXDKRALACDIA-UHFFFAOYSA-N 0.000 description 1
- UCSBCWBHZLSFGC-UHFFFAOYSA-N tributoxysilane Chemical compound CCCCO[SiH](OCCCC)OCCCC UCSBCWBHZLSFGC-UHFFFAOYSA-N 0.000 description 1
- JSQJUDVTRRCSRU-UHFFFAOYSA-N tributyl(chloro)silane Chemical compound CCCC[Si](Cl)(CCCC)CCCC JSQJUDVTRRCSRU-UHFFFAOYSA-N 0.000 description 1
- RYHGFALZTBTGDK-UHFFFAOYSA-N tributyl(iodo)silane Chemical compound CCCC[Si](I)(CCCC)CCCC RYHGFALZTBTGDK-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- CAPIMQICDAJXSB-UHFFFAOYSA-N trichloro(1-chloroethyl)silane Chemical compound CC(Cl)[Si](Cl)(Cl)Cl CAPIMQICDAJXSB-UHFFFAOYSA-N 0.000 description 1
- SNYHRPNTNQYJMD-UHFFFAOYSA-N trichloro(1-chloropropyl)silane Chemical compound CCC(Cl)[Si](Cl)(Cl)Cl SNYHRPNTNQYJMD-UHFFFAOYSA-N 0.000 description 1
- FMYXZXAKZWIOHO-UHFFFAOYSA-N trichloro(2-phenylethyl)silane Chemical compound Cl[Si](Cl)(Cl)CCC1=CC=CC=C1 FMYXZXAKZWIOHO-UHFFFAOYSA-N 0.000 description 1
- WDVUXWDZTPZIIE-UHFFFAOYSA-N trichloro(2-trichlorosilylethyl)silane Chemical compound Cl[Si](Cl)(Cl)CC[Si](Cl)(Cl)Cl WDVUXWDZTPZIIE-UHFFFAOYSA-N 0.000 description 1
- SIPHWXREAZVVNS-UHFFFAOYSA-N trichloro(cyclohexyl)silane Chemical compound Cl[Si](Cl)(Cl)C1CCCCC1 SIPHWXREAZVVNS-UHFFFAOYSA-N 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- ZOYFEXPFPVDYIS-UHFFFAOYSA-N trichloro(ethyl)silane Chemical compound CC[Si](Cl)(Cl)Cl ZOYFEXPFPVDYIS-UHFFFAOYSA-N 0.000 description 1
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 description 1
- GPWLZOISJZHVHX-UHFFFAOYSA-N trichloro(propan-2-yl)silane Chemical compound CC(C)[Si](Cl)(Cl)Cl GPWLZOISJZHVHX-UHFFFAOYSA-N 0.000 description 1
- DOEHJNBEOVLHGL-UHFFFAOYSA-N trichloro(propyl)silane Chemical compound CCC[Si](Cl)(Cl)Cl DOEHJNBEOVLHGL-UHFFFAOYSA-N 0.000 description 1
- LXEXBJXDGVGRAR-UHFFFAOYSA-N trichloro(trichlorosilyl)silane Chemical compound Cl[Si](Cl)(Cl)[Si](Cl)(Cl)Cl LXEXBJXDGVGRAR-UHFFFAOYSA-N 0.000 description 1
- ABDDAHLAEXNYRC-UHFFFAOYSA-N trichloro(trichlorosilylmethyl)silane Chemical compound Cl[Si](Cl)(Cl)C[Si](Cl)(Cl)Cl ABDDAHLAEXNYRC-UHFFFAOYSA-N 0.000 description 1
- QHAHOIWVGZZELU-UHFFFAOYSA-N trichloro(trichlorosilyloxy)silane Chemical compound Cl[Si](Cl)(Cl)O[Si](Cl)(Cl)Cl QHAHOIWVGZZELU-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 1
- 239000005052 trichlorosilane Substances 0.000 description 1
- WXZOJKGGVNTBBY-UHFFFAOYSA-N tricyclohexyl(iodo)silane Chemical compound C1CCCCC1[Si](C1CCCCC1)(I)C1CCCCC1 WXZOJKGGVNTBBY-UHFFFAOYSA-N 0.000 description 1
- XVYIJOWQJOQFBG-UHFFFAOYSA-N triethoxy(fluoro)silane Chemical compound CCO[Si](F)(OCC)OCC XVYIJOWQJOQFBG-UHFFFAOYSA-N 0.000 description 1
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 1
- JIOGKDWMNMIDEY-UHFFFAOYSA-N triethoxy-(2-triethoxysilylphenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1[Si](OCC)(OCC)OCC JIOGKDWMNMIDEY-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- PPLMQFARLJLZAO-UHFFFAOYSA-N triethyl(iodo)silane Chemical compound CC[Si](I)(CC)CC PPLMQFARLJLZAO-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- GBUPQQVBBMOHMJ-UHFFFAOYSA-N triiodo(1-triiodosilylethyl)silane Chemical compound I[Si](I)(I)C(C)[Si](I)(I)I GBUPQQVBBMOHMJ-UHFFFAOYSA-N 0.000 description 1
- OWPIUELMEJJOEM-UHFFFAOYSA-N triiodo(2-phenylethyl)silane Chemical compound I[Si](I)(I)CCC1=CC=CC=C1 OWPIUELMEJJOEM-UHFFFAOYSA-N 0.000 description 1
- ARIHFGQDMNMGQJ-UHFFFAOYSA-N triiodo(methyl)silane Chemical compound C[Si](I)(I)I ARIHFGQDMNMGQJ-UHFFFAOYSA-N 0.000 description 1
- HBVCQKOZPHBDAR-UHFFFAOYSA-N triiodo(phenyl)silane Chemical compound I[Si](I)(I)C1=CC=CC=C1 HBVCQKOZPHBDAR-UHFFFAOYSA-N 0.000 description 1
- GVSZXOJERRZCHO-UHFFFAOYSA-N triiodo(propan-2-yl)silane Chemical compound CC(C)[Si](I)(I)I GVSZXOJERRZCHO-UHFFFAOYSA-N 0.000 description 1
- GTLPSNWPFBXKQA-UHFFFAOYSA-N triiodo(propyl)silane Chemical compound CCC[Si](I)(I)I GTLPSNWPFBXKQA-UHFFFAOYSA-N 0.000 description 1
- DNAPJAGHXMPFLD-UHFFFAOYSA-N triiodosilane Chemical compound I[SiH](I)I DNAPJAGHXMPFLD-UHFFFAOYSA-N 0.000 description 1
- BWOVOXIQSOKSAH-UHFFFAOYSA-N triiodosilicon Chemical group I[Si](I)I BWOVOXIQSOKSAH-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- 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 1
- KBFAHPBJNNSTGX-UHFFFAOYSA-N trimethoxy-(3-trimethoxysilylphenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC([Si](OC)(OC)OC)=C1 KBFAHPBJNNSTGX-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical group CO[Si](OC)OC PZJJKWKADRNWSW-UHFFFAOYSA-N 0.000 description 1
- CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 1
- IXJNGXCZSCHDFE-UHFFFAOYSA-N triphenoxy(phenyl)silane Chemical compound C=1C=CC=CC=1O[Si](C=1C=CC=CC=1)(OC=1C=CC=CC=1)OC1=CC=CC=C1 IXJNGXCZSCHDFE-UHFFFAOYSA-N 0.000 description 1
- AMUIJRKZTXWCEA-UHFFFAOYSA-N triphenoxy(propyl)silane Chemical compound C=1C=CC=CC=1O[Si](OC=1C=CC=CC=1)(CCC)OC1=CC=CC=C1 AMUIJRKZTXWCEA-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
- QDOHRQCMIFOPEY-UHFFFAOYSA-N tripropoxy(2-tripropoxysilylethyl)silane Chemical compound CCCO[Si](OCCC)(OCCC)CC[Si](OCCC)(OCCC)OCCC QDOHRQCMIFOPEY-UHFFFAOYSA-N 0.000 description 1
- VUWVDNLZJXLQPT-UHFFFAOYSA-N tripropoxy(propyl)silane Chemical compound CCCO[Si](CCC)(OCCC)OCCC VUWVDNLZJXLQPT-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
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- ORBIWUVSNQKBNY-UHFFFAOYSA-N tris(3-bicyclo[2.2.1]heptanyl)-bromosilane Chemical compound C1C(C2)CCC2C1[Si](Br)(C1C2CCC(C2)C1)C1C(C2)CCC2C1 ORBIWUVSNQKBNY-UHFFFAOYSA-N 0.000 description 1
- DMFPULBEKRWMBR-UHFFFAOYSA-N tris(3-bicyclo[2.2.1]heptanyl)-chlorosilane Chemical compound C1C(C2)CCC2C1[Si](Cl)(C1C2CCC(C2)C1)C1C(C2)CCC2C1 DMFPULBEKRWMBR-UHFFFAOYSA-N 0.000 description 1
- YHRZMJOTERBNEE-UHFFFAOYSA-N tris(3-bicyclo[2.2.1]heptanyl)-iodosilane Chemical compound C1C(C2)CCC2C1[Si](I)(C1C2CCC(C2)C1)C1C(C2)CCC2C1 YHRZMJOTERBNEE-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
- 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
- QCKKBOHAYRLMQP-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]silane Chemical compound CC(C)(C)O[SiH](OC(C)(C)C)OC(C)(C)C QCKKBOHAYRLMQP-UHFFFAOYSA-N 0.000 description 1
- DJECDCLXTNZYDL-UHFFFAOYSA-N tritert-butyl(chloro)silane Chemical compound CC(C)(C)[Si](Cl)(C(C)(C)C)C(C)(C)C DJECDCLXTNZYDL-UHFFFAOYSA-N 0.000 description 1
- FUGWOYOEVNYBJX-UHFFFAOYSA-N tritert-butyl(iodo)silane Chemical compound CC(C)(C)[Si](I)(C(C)(C)C)C(C)(C)C FUGWOYOEVNYBJX-UHFFFAOYSA-N 0.000 description 1
- XMUJIPOFTAHSOK-UHFFFAOYSA-N undecan-2-ol Chemical compound CCCCCCCCCC(C)O XMUJIPOFTAHSOK-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
-
- 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
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Abstract
【解決手段】
本発明の有機シリカ系膜の形成方法は、−Si−O−Si−構造および−Si−CH2−Si−構造を有するケイ素化合物からなる塗膜を基材上に形成する工程と、前記塗膜を加熱する工程と、前記塗膜に紫外線を照射して硬化処理を行なう工程と、を含む。
【選択図】 なし
Description
(a)光酸発生剤、光塩基発生剤、増感剤などのイオン性物質、電荷キャリアもしくは腐食性化合物の発生源を含まず、短時間で硬化可能な有機シリカゾル組成物、
(b)トランジスタ構造へのダメージが無く、枚葉プロセスで処理可能な有機シリカ系膜の硬化方法、
(c)吸湿性がなく疎水性に富んだ有機シリカ系膜、および
(d)銅ダマシン構造の形成に耐えうる機械的強度を有する有機シリカ系膜、
がLSI用半導体装置の低誘電率層間絶縁膜およびその形成方法として望まれている。
−Si−O−Si−構造および−Si−CH2−Si−構造を有するケイ素化合物からなる塗膜を基材上に形成する工程と、
前記塗膜を加熱する工程と、
前記塗膜に紫外線を照射して硬化処理を行なう工程と、
を含む。
本発明の有機シリカ系膜は、上記本発明の有機シリカ系膜の形成方法により得られ、比誘電率が1.5〜3.5でありかつ膜密度が0.7〜1.3g/cm3であることができる。
(A)ポリカルボシランの存在下、(B)加水分解性基含有シランモノマーを加水分解縮合して得られる加水分解縮合物と、
有機溶媒と、
を含み、
上記本発明の有機シリカ系膜の形成方法において前記塗膜を形成するために使用される。
本発明の有機シリカ系膜の形成方法は、−Si−O−Si−構造および−Si−CH2−Si−構造を有するケイ素化合物(以下、単に「ケイ素化合物」ともいう)からなる塗膜を基材上に形成する工程と、前記塗膜を加熱する工程と、前記塗膜に紫外線を照射して硬化処理を行なう工程と、を含む。
本発明において、まず、−Si−O−Si−構造および−Si−CH2−Si−構造を有するケイ素化合物からなる塗膜を基材上に形成する。
本発明において、ケイ素化合物からなる塗膜を形成するための好ましい膜形成用組成物は、ポリマー成分として、ポリカルボシランおよびポリシロキサンを含むものが好ましい。本発明の膜形成用組成物は、ポリカルボシランおよびポリシロキサンを有機溶剤に溶解して製造することもできるが、特に、(A)ポリカルボシラン(以下、「(A)成分」ともいう)の存在下、(B)加水分解性基含有シランモノマー(以下、「(B)成分」ともいう)を加水分解縮合して得られた加水分解縮合物(以下、単に「加水分解縮合物」ともいう)を有機溶媒に溶解することにより得られるものであることが好ましい。
加水分解縮合物のポリスチレン換算重量平均分子量(Mw)は、1,500〜500,000であるのが好ましく、2,000〜200,000であるのがより好ましく、2,000〜100,000であるのがさらに好ましい。加水分解縮合物のポリスチレン換算重量平均分子量が1,500未満であると、目的とする比誘電率が得られない場合があり、一方、500,000を超えると、塗膜の面内均一性が劣る場合がある。
本発明において、(A)成分である(A)ポリカルボシランは、例えば、下記一般式(1)で表されるポリカルボシラン化合物(以下、「化合物1」ともいう)であることができる。
(式中、R8は、水素原子、ハロゲン原子、ヒドロキシ基、アルコキシ基、アシロキシ基、スルホン基、メタンスルホン基、トリフルオロメタンスルホン基、アルキル基、アルケニル基、およびアリール基からなる群より選ばれる基を示し、R9はハロゲン原子、ヒドロキシ基、アルコキシ基、アシロキシ基、スルホン基、メタンスルホン基、トリフルオロメタンスルホン基、アルキル基、アルケニル基、およびアリール基からなる群より選ばれる基を示し、R10,R11は同一または異なり、ハロゲン原子、ヒドロキシ基、アルコキシ基、アシロキシ基、スルホン基、メタンスルホン基、トリフルオロメタンスルホン基、炭素数2〜6のアルキル基、アルケニル基、およびアリール基からなる群より選ばれる基を示し、R12〜R14は同一または異なり、メチレン基、アルキレン基、アルケニレン基、およびアリーレン基からなる群より選ばれる基を示し、R12〜R14の少なくとも一つはメチレン基であり、x,y,zは、それぞれ0〜10,000の数を示し、5<x+y+z<10,000の条件を満たす。ただし、x=0の場合には、R9、R10、R11のいずれかひとつは、ハロゲン原子、ヒドロキシ基、アルコキシ基、アシロキシ基、スルホン基、メタンスルホン基、またはトリフルオロメタンスルホン基である。)
本発明において、(B)加水分解性基含有シランモノマーは、加水分解性基を有するシランモノマーであれば特に限定されないが、例えば、下記一般式(2)で表される化合物(以下、「化合物2」ともいう)および下記一般式(3)で表される化合物(以下、「化合物3」ともいう)の群から選ばれた少なくとも1種のシラン化合物であることができる。
(式中、R1は水素原子,フッ素原子または1価の有機基を示し、Xはハロゲン原子、ヒドロキシ基、アルコキシ基、およびアシロキシ基から選ばれる基を示し、aは0〜3の整数を示す。)
R2 bY3−bSi−(R4)d−SiZ3−cR3 c ・・・・・(3)
(式中、R2,R3は同一または異なり、それぞれ1価の有機基を示し、bおよびcは同一または異なり、0〜2の整数を示し、R4は酸素原子,フェニレン基または−(CH2)e−で表される基(ここで、eは1〜6の整数である)を示し、YおよびZは同一または異なり、ハロゲン原子、ヒドロキシ基、アルコキシ基、およびアシロキシ基から選ばれる基を示し、dは0または1を示す。)
前記一般式(2)において、R1は水素原子,フッ素原子または1価の有機基である。1価の有機基としては、アルキル基、アルケニル基、アリール基などを挙げることができる。また、一般式(2)において、R2は1価の有機基、特にアルキル基、アルケニル基、またはフェニル基であることが好ましい。
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、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−iso−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、ビニルトリメトキシシラン、ビニルトリエトキシシラン、ビニルトリ−n−プロポキシシラン、ビニルトリ−iso−プロポキシシラン、ビニルトリ−n−ブトキシシラン、ビニルトリ−sec−ブトキシシラン、ビニルトリ−tert−ブトキシシラン、ビニ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−iso−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、i−プロピルトリメトキシシラン、i−プロピルトリエトキシシラン、i−プロピルトリ−n−プロポキシシラン、i−プロピルトリ−iso−プロポキシシラン、i−プロピルトリ−n−ブトキシシラン、i−プロピルトリ−sec−ブトキシシラン、i−プロピルトリ−tert−ブトキシシラン、i−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−iso−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−iso−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、t−ブチルトリメトキシシラン、t−ブチルトリエトキシシラン、t−ブチルトリ−n−プロポキシシラン、t−ブチルトリ−iso−プロポキシシラン、t−ブチルトリ−n−ブトキシシラン、t−ブチルトリ−sec−ブトキシシラン、t−ブチルトリ−tert−ブトキシシラン、t−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−iso−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;
ジメチルジメトキシシラン、ジメチルジエトキシシラン、ジメチル−ジ−n−プロポキシシラン、ジメチル−ジ−iso−プロポキシシラン、ジメチル−ジ−n−ブトキシシラン、ジメチル−ジ−sec−ブトキシシラン、ジメチル−ジ−tert−ブトキシシラン、ジメチルジフェノキシシラン、ジエチルジメトキシシラン、ジエチルジエトキシシラン、ジエチル−ジ−n−プロポキシシラン、ジエチル−ジ−iso−プロポキシシラン、ジエチル−ジ−n−ブトキシシラン、ジエチル−ジ−sec−ブトキシシラン、ジエチル−ジ−tert−ブトキシシラン、ジエチルジフェノキシシラン、ジ−n−プロピルジメトキシシラン、ジ−n−プロピルジエトキシシラン、ジ−n−プロピル−ジ−n−プロポキシシラン、ジ−n−プロピル−ジ−iso−プロポキシシラン、ジ−n−プロピル−ジ−n−ブトキシシラン、ジ−n−プロピル−ジ−sec−ブトキシシラン、ジ−n−プロピル−ジ−tert−ブトキシシラン、ジ−n−プロピル−ジ−フェノキシシラン、ジ−iso−プロピルジメトキシシラン、ジ−iso−プロピルジエトキシシラン、ジ−iso−プロピル−ジ−n−プロポキシシラン、ジ−iso−プロピル−ジ−iso−プロポキシシラン、ジ−iso−プロピル−ジ−n−ブトキシシラン、ジ−iso−プロピル−ジ−sec−ブトキシシラン、ジ−iso−プロピル−ジ−tert−ブトキシシラン、ジ−iso−プロピル−ジ−フェノキシシラン、ジ−n−ブチルジメトキシシラン、ジ−n−ブチルジエトキシシラン、ジ−n−ブチル−ジ−n−プロポキシシラン、ジ−n−ブチル−ジ−iso−プロポキシシラン、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−iso−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−iso−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−iso−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、ジビニルトリメトキシシランなど;
テトラクロロシラン、テトラブロモシラン、テトラヨードシラン、トリクロロシラン、トリブロモシラン、トリヨードシラン、メチルトリクロロシラン、エチルトリクロロシラン、n−プロピルトリクロロシラン、イソプロピルトリクロロシラン、n−ブチルトリクロロシラン、t−ブチルトリクロロシラン、シクロヘキシルトリクロロシラン、フェネチルトリクロロシラン、2−ノルボルニルトリクロロシラン、ビニルトリクロロシラン、フェニルトリクロロシラン、メチルトリブロモシラン、エチルトリブロモシラン、n−プロピルトリブロモシラン、イソプロピルトリブロモシラン、n−ブチルトリブロモシラン、t−ブチルトリブロモシラン、シクロヘキシルトリブロモシラン、フェネチルトリブロモシラン、2−ノルボルニルトリブロモシラン、ビニルトリブロモシラン、フェニルトリブロモシラン、メチルトリヨードシラン、エチルトリヨードシラン、n−プロピルトリヨードシラン、イソプロピルトリヨードシラン、n−ブチルトリヨードシラン、t−ブチルトリヨードシラン、シクロヘキシルトリヨードシラン、フェネチルトリヨードシラン、2−ノルボルニルトリヨードシラン、ビニルトリヨードシラン、フェニルトリヨードシラン、ジメチルジクロロシラン、ジエチルジクロロシラン、ジ−n−プロピルジクロロシラン、ジイソプロピルジクロロシラン、ジ−n−ブチルジクロロシラン、ジ−t−ブチルジクロロシラン、ジシクロヘキシルジクロロシラン、ジフェネチルジクロロシラン、ジ−2−ノルボルニルジクロロシラン、ジビニルジクロロシラン、ジフェニルジクロロシラン、ジメチルジブロモシラン、ジエチルジブロモシラン、ジ−n−プロピルジブロモシラン、ジイソプロピルジブロモシラン、ジ−n−ブチルジブロモシラン、ジ−t−ブチルジブロモシラン、ジシクロヘキシルジブロモシラン、ジフェネチルジブロモシラン、ジ−2−ノルボルニルジブロモシラン、ジビニルジブロモシラン、ジフェニルジブロモシラン、ジメチルジヨードシラン、ジエチルジヨードシラン、ジ−n−プロピルジヨードシラン、ジイソプロピルジヨードシラン、ジ−n−ブチルジヨードシラン、ジ−t−ブチルジヨードシラン、ジシクロヘキシルジヨードシラン、ジフェネチルジヨードシラン、ジ−2−ノルボルニルジヨードシラン、ジビニルジヨードシラン、ジフェニルジヨードシラン、トリメチルクロロシラン、トリエチルクロロシラン、トリ−n−プロピルクロロシラン、トリイソプロピルクロロシラン、トリ−n−ブチルクロロシラン、トリ−t−ブチルクロロシラン、トリシクロヘキシルクロロシラン、トリフェネチルクロロシラン、トリ−2−ノルボルニルクロロシラン、トリビニルクロロシラン、トリフェニルクロロシラン、トリメチルブロモシラン、トリエチルブロモシラン、トリ−n−プロピルブロモシラン、トリイソプロピルブロモシラン、トリ−n−ブチルブロモシラン、トリ−t−ブチルブロモシラン、トリシクロヘキシルブロモシラン、トリフェネチルブロモシラン、トリ−2−ノルボルニルブロモシラン、トリビニルブロモシラン、トリフェニルブロモシラン、トリメチルヨードシラン、トリエチルヨードシラン、トリ−n−プロピルヨードシラン、トリイソプロピルヨードシラン、トリ−n−ブチルヨードシラン、トリ−t−ブチルヨードシラン、トリシクロヘキシルヨードシラン、トリフェネチルヨードシラン、トリ−2−ノルボルニルヨードシラン、トリビニルヨードシラン、トリフェニルヨードシランなどのケイ素化合物を挙げることができる。これらの化合物は1種単独でも使用できるし、2種以上を混合して使用することもできる。
化合物3のうち、前記一般式(3)において、R2,R3で表される1価の有機基としては、先の一般式(2)と同様の有機基を挙げることができる。
本発明の加水分解縮合物は、(A)成分の存在下に、(B)成分を加水分解縮合することにより得られる。
トリエトキシ・モノ(アセチルアセトナート)ジルコニウム、トリ−n−プロポキシ・モノ(アセチルアセトナート)ジルコニウム、トリ−i−プロポキシ・モノ(アセチルアセトナート)ジルコニウム、トリ−n−ブトキシ・モノ(アセチルアセトナート)ジルコニウム、トリ−sec−ブトキシ・モノ(アセチルアセトナート)ジルコニウム、トリ−t−ブトキシ・モノ(アセチルアセトナート)ジルコニウム、ジエトキシ・ビス(アセチルアセトナート)ジルコニウム、ジ−n−プロポキシ・ビス(アセチルアセトナート)ジルコニウム、ジ−i−プロポキシ・ビス(アセチルアセトナート)ジルコニウム、ジ−n−ブトキシ・ビス(アセチルアセトナート)ジルコニウム、ジ−sec−ブトキシ・ビス(アセチルアセトナート)ジルコニウム、ジ−t−ブトキシ・ビス(アセチルアセトナート)ジルコニウム、モノエトキシ・トリス(アセチルアセトナート)ジルコニウム、モノ−n−プロポキシ・トリス(アセチルアセトナート)ジルコニウム、モノ−i−プロポキシ・トリス(アセチルアセトナート)ジルコニウム、モノ−n−ブトキシ・トリス(アセチルアセトナート)ジルコニウム、モノ−sec−ブトキシ・トリス(アセチルアセトナート)ジルコニウム、モノ−t−ブトキシ・トリス(アセチルアセトナート)ジルコニウム、テトラキス(アセチルアセトナート)ジルコニウム、トリエトキシ・モノ(エチルアセトアセテート)ジルコニウム、トリ−n−プロポキシ・モノ(エチルアセトアセテート)ジルコニウム、トリ−i−プロポキシ・モノ(エチルアセトアセテート)ジルコニウム、トリ−n−ブトキシ・モノ(エチルアセトアセテート)ジルコニウム、トリ−sec−ブトキシ・モノ(エチルアセトアセテート)ジルコニウム、トリ−t−ブトキシ・モノ(エチルアセトアセテート)ジルコニウム、ジエトキシ・ビス(エチルアセトアセテート)ジルコニウム、ジ−n−プロポキシ・ビス(エチルアセトアセテート)ジルコニウム、ジ−i−プロポキシ・ビス(エチルアセトアセテート)ジルコニウム、ジ−n−ブトキシ・ビス(エチルアセトアセテート)ジルコニウム、ジ−sec−ブトキシ・ビス(エチルアセトアセテート)ジルコニウム、ジ−t−ブトキシ・ビス(エチルアセトアセテート)ジルコニウム、モノエトキシ・トリス(エチルアセトアセテート)ジルコニウム、モノ−n−プロポキシ・トリス(エチルアセトアセテート)ジルコニウム、モノ−i−プロポキシ・トリス(エチルアセトアセテート)ジルコニウム、モノ−n−ブトキシ・トリス(エチルアセトアセテート)ジルコニウム、モノ−sec−ブトキシ・トリス(エチルアセトアセテート)ジルコニウム、モノ−t−ブトキシ・トリス(エチルアセトアセテート)ジルコニウム、テトラキス(エチルアセトアセテート)ジルコニウム、モノ(アセチルアセトナート)トリス(エチルアセトアセテート)ジルコニウム、ビス(アセチルアセトナート)ビス(エチルアセトアセテート)ジルコニウム、トリス(アセチルアセトナート)モノ(エチルアセトアセテート)ジルコニウムなどのジルコニウムキレート化合物;
トリス(アセチルアセトナート)アルミニウム、トリス(エチルアセトアセテート)アルミニウムなどのアルミニウムキレート化合物;
などを挙げることができ、好ましくはチタンまたはアルミニウムのキレート化合物、特に好ましくはチタンのキレート化合物を挙げることができる。これらの金属キレート触媒は、1種あるいは2種以上を同時に使用してもよい。
酢酸、プロピオン酸、ブタン酸、ペンタン酸、ヘキサン酸、ヘプタン酸、オクタン酸、ノナン酸、デカン酸、シュウ酸、マレイン酸、メチルマロン酸、アジピン酸、セバシン酸、没食子酸、酪酸、メリット酸、アラキドン酸、シキミ酸、2−エチルヘキサン酸、オレイン酸、ステアリン酸、リノール酸、リノレイン酸、サリチル酸、安息香酸、p−アミノ安息香酸、p−トルエンスルホン酸、ベンゼンスルホン酸、モノクロロ酢酸、ジクロロ酢酸、トリクロロ酢酸、トリフルオロ酢酸、ギ酸、マロン酸、スルホン酸、フタル酸、フマル酸、クエン酸、酒石酸、コハク酸、フマル酸、イタコン酸、メサコン酸、シトラコン酸、リンゴ酸、グルタル酸の加水分解物、無水マレイン酸の加水分解物、無水フタル酸の加水分解物などの有機酸を挙げることができ、有機カルボン酸をより好ましい例として挙げることができる。これらの酸触媒は、1種あるいは2種以上を同時に使用してもよい。
本発明の膜形成用組成物においては、加水分解縮合物、ならびに必要に応じてさらに後述するその他の成分を有機溶媒に溶解あるいは分散させることができる。
エチレングリコール、1,2−プロピレングリコール、1,3−ブチレングリコール、2,4−ペンタンジオール、2−メチル−2,4−ペンタンジオール、2,5−ヘキサンジオール、2,4−ヘプタンジオール、2−エチル−1,3−ヘキサンジオール、ジエチレングリコール、ジプロピレングリコール、トリエチレングリコール、トリプロピレングリコールなどの多価アルコール系溶媒;
エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、エチレングリコールモノプロピルエーテル、エチレングリコールモノブチルエーテル、エチレングリコールモノヘキシルエーテル、エチレングリコールモノフェニルエーテル、エチレングリコールモノ−2−エチルブチルエーテル、ジエチレングリコールモノメチルエーテル、ジエチレングリコールモノエチルエーテル、ジエチレングリコールモノプロピルエーテル、ジエチレングリコールモノブチルエーテル、ジエチレングリコールモノヘキシルエーテル、プロピレングリコールモノメチルエーテル、プロピレングリコールモノエチルエーテル、プロピレングリコールモノプロピルエーテル、プロピレングリコールモノブチルエーテル、ジプロピレングリコールモノメチルエーテル、ジプロピレングリコールモノエチルエーテル、ジプロピレングリコールモノプロピルエーテルなどの多価アルコール部分エーテル系溶媒;
などを挙げることができる。これらのアルコール系溶媒は、1種あるいは2種以上を同時に使用してもよい。
本発明の膜形成用組成物においては、(A)成分および/または(B)成分の加水分解反応および/または縮合反応を促進するための反応促進剤を含まないことができる。ここで、「反応促進剤」とは、反応開始剤、触媒(酸発生剤、塩基発生剤)および紫外線吸収機能を有する増感剤のいずれか、またはこれらのうち2種以上の組合せを意味する。
界面活性剤としては、たとえば、ノニオン系界面活性剤、アニオン系界面活性剤、カチオン系界面活性剤、両性界面活性剤などが挙げられ、さらには、フッ素系界面活性剤、シリコーン系界面活性剤、ポリアルキレンオキシド系界面活性剤、ポリ(メタ)アクリレート系界面活性剤などを挙げることができる。
シランカップリング剤としては、例えば、3−グリシジロキシプロピルトリメトキシシラン、3−アミノグリシジロキシプロピルトリエトキシシラン、3−メタクリロキシプロピルトリメトキシシラン、3−グリシジロキシプロピルメチルジメトキシシラン、1−メタクリロキシプロピルメチルジメトキシシラン、3−アミノプロピルトリメトキシシラン、3−アミノプロピルトリエトキシシラン、2−アミノプロピルトリメトキシシラン、2−アミノプロピルトリエトキシシラン、N−(2−アミノエチル)−3−アミノプロピルトリメトキシシラン、N−(2−アミノエチル)−3−アミノプロピルメチルジメトキシシラン、3−ウレイドプロピルトリメトキシシラン、3−ウレイドプロピルトリエトキシシラン、N−エトキシカルボニル−3−アミノプロピルトリメトキシシラン、N−エトキシカルボニル−3−アミノプロピルトリエトキシシラン、N−トリエトキシシリルプロピルトリエチレントリアミン、N−トリエトキシシリルプロピルトリエチレントリアミン、10−トリメトキシシリル−1,4,7−トリアザデカン、10−トリエトキシシリル−1,4,7−トリアザデカン、9−トリメトキシシリル−3,6−ジアザノニルアセテート、9−トリエトキシシリル−3,6−ジアザノニルアセテート、N−ベンジル−3−アミノプロピルトリメトキシシラン、N−ベンジル−3−アミノプロピルトリエトキシシラン、N−フェニル−3−アミノプロピルトリメトキシシラン、N−フェニル−3−アミノプロピルトリエトキシシラン、N−ビス(オキシエチレン)−3−アミノプロピルトリメトキシシラン、N−ビス(オキシエチレン)−3−アミノプロピルトリエトキシシランなどが挙げられる。これらは、1種あるいは2種以上を同時に使用してもよい。
本発明の有機シリカ系膜の形成方法は、前述したように、ケイ素化合物からなる塗膜を基材上に形成する工程と、前記塗膜を加熱する工程と、前記塗膜に紫外線を照射して硬化処理を行なう工程と、を含む。
本発明の有機シリカ系膜の形成方法において、ケイ素化合物からなる塗膜を形成する際には、例えば、スピンコート、浸漬法、ロールコート法、スプレー法などの塗装手段が用いられる。塗布の対象となる基材としては、特に限定されないが、例えば、Si、SiO2、SiN、SiC、SiCN、SiON等のSi含有層が挙げられる。基材としては具体的には、上記材料からなる半導体基板が挙げられる。
形成された塗膜は、その後、常温で乾燥するか、あるいは80〜600℃程度の温度で、通常、5〜240分間程度加熱して乾燥することにより、ガラス質または巨大高分子の塗膜を形成することができる。
紫外線の照射においては、好ましくは250nm以下、より好ましくは150〜250mの波長を含む紫外線により行なうことができる。この範囲の波長の紫外線を用いることにより、紫外線に活性な反応促進剤を用いることなく、有機シリカゾル中の分子の縮合反応を低温かつ短時間で行なうことができる。紫外線の波長が250nmより長いと、有機シリカゾルにおいて充分な縮合反応の促進効果が認められない。また、紫外線の波長が150nmより短いと、有機シリカゾルにおいて、有機基の分解やケイ素原子に結合している有機基の脱離が生じやすくなる。
本発明の有機シリカ系膜は、上記本発明の有機シリカ系膜の形成方法によって得られる。本発明の有機シリカ系膜において、炭素含量(原子数)は、11〜26モル%であり、好ましくは12〜20モル%の範囲である。炭素含量が上記の範囲にあると、紫外線照射によってより短時間で塗膜を硬化させることができ、かつ、得られる有機シリカ系膜の低比誘電率を維持しながら機械的強度を向上させることができる。炭素含量が11モル%より少ないと、固相反応での拡散障壁が高く、紫外線を照射しても反応が促進されにくく、プラズマ耐性の劣る膜となり、一方、炭素含量が26モル%より多いと、分子の運動性が高まりすぎて、弾性率が低く、場合によってはガラス転移点を示すような膜となり好ましくない。
(a)ケイ素化合物が特定の組成と炭素含量を有するため、比誘電率、弾性率、プラズマ耐性、および薬液耐性などの絶縁膜特性に優れ、かつ、低温かつ短時間で形成できること、
(b)塗膜の形成に使用される本発明の膜形成用組成物が、紫外線活性な酸発生剤、塩基発生剤、増感剤などのイオン性物質、電荷キャリアもしくは腐食性化合物の発生源を含まなくてもよいため、半導体装置への汚染物質を含まないこと、
(c)RIEなどの半導体プロセスによるトランジスタ構造へのダメージが極めて少なく、かつ枚葉プロセスで処理可能な硬化方法を採用できること、
(d)疎水性が高く、吸湿性が低いため、低い比誘電率を維持できること、および
(e)弾性率などの機械的強度が優れており、例えば銅ダマシン構造の形成に耐えうること、
などの特徴を有する。この特徴により、絶縁性、塗布膜の均一性、誘電率特性、塗膜の弾性率、塗膜の密着性、プラズマ耐性、および薬液耐性に優れる。
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、次のようにして行なった。
下記条件によるゲルパーミエーションクロマトグラフィー(GPC)法により測定した。
試料:テトラヒドロフランを溶媒として使用し、ポリマー1gを100ccのテトラヒドロフランに溶解して調製した。
標準ポリスチレン:米国プレッシャーケミカル社製の標準ポリスチレンを使用した。
装置:米国ウオーターズ社製の高温高速ゲル浸透クロマトグラム(モデル150−C ALC/GPC)
カラム:昭和電工(株)製のSHODEX A−80M(長さ50cm)
測定温度:40℃
流速:1cc/分
得られたポリマー膜に対して蒸着法によりアルミニウム電極パターンを形成させ、比誘電率測定用サンプルを作成した。該サンプルを周波数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法により室温における当該塗膜の比誘電率を測定した。
2.1.2と同様にして200℃における比誘電率の測定を行ない、2.1.2における比誘電率との差を示した。
得られたポリマー膜について、SAW(Surface Acoustic Wave)法により測定した。
硬化させた有機シリカ系膜にアンモニアプラズマを30秒間照射した後に膜の比誘電率を測定し、プラズマ照射前後で上昇した比誘電率の値によって格付けした。
A:比誘電率の上昇値が0.2未満
B:比誘電率の上昇値が0.2以上0.5未満
C:比誘電率の上昇値が0.5以上
硬化させた有機シリカ膜を、pH12のトリエタノールアミン水溶液に室温で10分間浸漬した後水洗し、表面の水滴を窒素ブローで乾燥させた後に比誘電率を測定し、試験前後で上昇した比誘電率の値によって格付けした。
A:比誘電率の上昇値が0.1未満
B:比誘電率の上昇値が0.1以上0.3未満
C:比誘電率の上昇値が0.3以上
各合成例において、ケイ素化合物(加水分解縮合物)の合成時に使用したシランモノマーが100%加水分解縮合したときに得られる加水分解縮合物中の炭素含量を計算によって算出した。
2.2.1.合成例1
石英製セパラブルフラスコ中で、下記式(4)で表される構造単位を有するポリカルボシランA1(重量平均分子量800)3.14g、メチルトリメトキシシラン23.10g、テトラエトキシシラン15.14gおよび40%メチルアミン水溶液2.00gをエタノール327.72gに溶解させたのち、スリーワンモーターで攪拌させ、溶液温度を55℃に安定させた。次に、イオン交換水60.76gおよびエタノール268.13gの混合溶液を1時間かけて溶液に添加した。
石英製セパラブルフラスコ中で、合成例1で使用したポリカルボシランA112.55g、メチルトリメトキシシラン17.41g、テトラプロポキシシラン8.45g、および20%水酸化テトラプロピルアンモニウム15.30gをエタノール259.74gに溶解させたのち、スリーワンモーターで攪拌させ、溶液温度を55℃に安定させた。次に、イオン交換水50.2gおよびエタノール317.46gの混合溶液を1時間かけて溶液に添加した。
石英製セパラブルフラスコ中で、下記式(5)で表される構造単位(m、nの存在比 m:n=2:3)を有するポリカルボシランA2(重量平均分子量750)31.72g、メチルトリメトキシシラン11.61g、およびテトラメトキシシラン3.24gを、プロピレングリコールモノエチルエーテル溶液639.78gに溶解させたのち、スリーワンモーターで攪拌させ、溶液温度を55℃に安定させた。次に、シュウ酸0.076gを溶解させたイオン交換水13.58gを1時間かけて溶液に添加した。その後、50℃で3時間反応させたのち、反応液を室温まで冷却した。続いて、反応液にプロピレングリコールモノエチルエーテル653.06gを加えた後、この反応液を固形分濃度が10%となるまで減圧下で濃縮し、膜形成用組成物Cを得た。この組成物は、炭素含量23.17モル%、重量平均分子量3,200、Si−CH2−Si/Si−O−Si(モル比)1.607であった。
石英製セパラブルフラスコ中で、下記式(6)で表される構造単位を有するポリカルボシランA3(重量平均分子量860)47.37gをプロピレングリコールモノエチルエーテル溶液638.02gに溶解させたのち、スリーワンモーターで攪拌させ、溶液温度を55℃に安定させた。次に、シュウ酸0.08gを溶解させたイオン交換水14.52gを1時間かけて溶液に添加した。その後、50℃で3時間反応させたのち、反応液を室温まで冷却した。続いて、反応液にプロピレングリコールモノエチルエーテル652.22gを加えた後、この反応液を固形分濃度が10%となるまで減圧下で濃縮し、膜形成用組成物Dを得た。この組成物は、炭素含量23.53モル%、重量平均分子量2,700、Si−CH2−Si/Si−O−Si(モル比)2.00であった。
石英製セパラブルフラスコ中で、メチルトリメトキシシラン25.07g、テトラエトキシシラン16.82g、および40%メチルアミン水溶液2.07gを、エタノール266.69gに溶解させたのち、スリーワンモーターで攪拌させ、溶液温度を55℃に安定させた。次に、イオン交換水62.79gおよびエタノール388.75gの混合溶液を1時間かけて溶液に添加した。
石英製セパラブルフラスコ中で、合成例3で使用したポリカルボシランA235.68g、メチルトリメトキシシラン5.80g、テトラメトキシシラン1.62gを、プロピレングリコールモノエチルエーテル溶液647.32gに溶解させたのち、スリーワンモーターで攪拌させ、溶液温度を55℃に安定させた。次に、シュウ酸0.052gを溶解させたイオン交換水9.51gを1時間かけて溶液に添加した。その後、60℃で12時間反応させたのち、反応液を室温まで冷却した。続いて、反応液にプロピレングリコールモノエチルエーテル653.06gを加えた後、この反応液を固形分濃度が10%となるまで減圧下で濃縮し、膜形成用組成物Fを得た。この組成物は、炭素含量23.88モル%、重量平均分子量4,400、Si−CH2−Si/Si−O−Si(モル比)2.580であった。
石英製セパラブルフラスコ中で、合成例4で使用したポリカルボシランA34.74g、メチルトリメトキシシラン20.70g、テトラメトキシシラン53.97gを、プロピレングリコールモノエチルエーテル溶液568.21gに溶解させたのち、スリーワンモーターで攪拌させ、溶液温度を55℃に安定させた。次に、シュウ酸0.090gを溶解させたイオン交換水52.10gを1時間かけて溶液に添加した。その後、60℃で12時間反応させたのち、反応液を室温まで冷却した。続いて、反応液にプロピレングリコールモノエチルエーテル619.15gを加えた後、この反応液を固形分濃度が10%となるまで減圧下で濃縮し、膜形成用組成物Gを得た。この組成物は、炭素含量10.34モル%、重量平均分子量4,400、Si−CH2−Si/Si−O−Si(モル比)0.056であった。
合成例1−7で得られた組成物をそれぞれ、スピンコート法でシリコンウエハ上に塗布したのち、ホットプレート上にて90℃で1分間、次いで窒素雰囲気下にて200℃で1分間基板を乾燥し、さらに表1に示す硬化条件で基板を焼成した。焼成後に得られたポリマー膜(以下、「シリカ系膜」という)を前記評価方法のとおり評価した。評価結果を表1に示す。
Claims (14)
- −Si−O−Si−構造および−Si−CH2−Si−構造を有するケイ素化合物からなる塗膜を基材上に形成する工程と、
前記塗膜を加熱する工程と、
前記塗膜に紫外線を照射して硬化処理を行なう工程と、
を含む、有機シリカ系膜の形成方法。 - 請求項1において、
前記ケイ素化合物中に、−Si−O−Si−構造および−Si−CH2−Si−構造が−Si−CH2−Si−/−Si−O−Si−(モル比)で0.025〜2.00の割合で存在する、有機シリカ系膜の形成方法。 - 請求項1または2において、
前記ケイ素化合物中の炭素含量が11〜26モル%である、有機シリカ系膜の形成方法。 - 請求項1ないし3のいずれかにおいて、
前記紫外線は、波長が250nm以下である、有機シリカ系膜の形成方法。 - 請求項1ないし4のいずれかにおいて、
加熱および紫外線の照射を同時に行なう、有機シリカ系膜の形成方法。 - 請求項1ないし5のいずれかにおいて、
前記加熱は300〜450℃で行われる、有機シリカ系膜の形成方法。 - 請求項1ないし6のいずれかにおいて、
前記紫外線の照射が酸素の非存在下で行われる、有機シリカ系膜の形成方法。 - 請求項1ないし7のいずれかにおいて、
前記ケイ素化合物が、(A)ポリカルボシランの存在下、(B)加水分解性基含有シランモノマーを加水分解縮合して得られた加水分解縮合物である、有機シリカ系膜の形成方法。 - 請求項1ないし8のいずれかに記載された有機シリカ系膜の形成方法により得られ、比誘電率が1.5〜3.5でありかつ膜密度が0.7〜1.3g/cm3である有機シリカ系膜。
- 請求項9に記載の有機シリカ系膜を層間絶縁膜として用いた、配線構造体。
- 請求項10に記載の配線構造体を含む、半導体装置。
- (A)ポリカルボシランの存在下、(B)加水分解性基含有シランモノマーを加水分解縮合して得られる加水分解縮合物と、
有機溶媒と、
を含み、請求項1ないし8のいずれかに記載の有機シリカ系膜の形成方法において前記塗膜を形成するために使用される膜形成用組成物。 - 請求項12において、
前記加水分解縮合物は、炭素原子を11〜26モル%含有する、膜形成用組成物。 - 請求項12または13において、
前記(A)成分の使用量が前記(B)成分の完全加水分解縮合物に換算した100重量部に対して、1〜1000重量部である、膜形成用組成物。
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JP (1) | JP5110239B2 (ja) |
KR (1) | KR101163251B1 (ja) |
TW (1) | TW200613375A (ja) |
WO (1) | WO2005108468A1 (ja) |
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EP1746122A1 (en) | 2007-01-24 |
TW200613375A (en) | 2006-05-01 |
TWI356830B (ja) | 2012-01-21 |
KR101163251B1 (ko) | 2012-07-05 |
KR20070010081A (ko) | 2007-01-19 |
US20080268264A1 (en) | 2008-10-30 |
WO2005108468A1 (ja) | 2005-11-17 |
JP5110239B2 (ja) | 2012-12-26 |
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US8268403B2 (en) | 2012-09-18 |
EP1746122B1 (en) | 2013-06-12 |
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