JP4877486B2 - 絶縁膜形成用組成物およびその製造方法、ならびにシリカ系絶縁膜およびその形成方法 - Google Patents
絶縁膜形成用組成物およびその製造方法、ならびにシリカ系絶縁膜およびその形成方法 Download PDFInfo
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- JP4877486B2 JP4877486B2 JP2006151339A JP2006151339A JP4877486B2 JP 4877486 B2 JP4877486 B2 JP 4877486B2 JP 2006151339 A JP2006151339 A JP 2006151339A JP 2006151339 A JP2006151339 A JP 2006151339A JP 4877486 B2 JP4877486 B2 JP 4877486B2
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- IVRXTRZVBJSOLZ-UHFFFAOYSA-N tri(butan-2-yloxy)-[2-tri(butan-2-yloxy)silylphenyl]silane Chemical compound CCC(C)O[Si](OC(C)CC)(OC(C)CC)C1=CC=CC=C1[Si](OC(C)CC)(OC(C)CC)OC(C)CC IVRXTRZVBJSOLZ-UHFFFAOYSA-N 0.000 description 1
- 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
- FURAZISLABARIL-UHFFFAOYSA-N tri(butan-2-yloxy)-[di(butan-2-yloxy)methylsilylmethyl]silane Chemical compound CCC(C)OC(OC(C)CC)[SiH2]C[Si](OC(C)CC)(OC(C)CC)OC(C)CC FURAZISLABARIL-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
- MHQDJCZAQGWXBC-UHFFFAOYSA-N tri(butan-2-yloxy)-ethenylsilane Chemical compound CCC(C)O[Si](OC(C)CC)(OC(C)CC)C=C MHQDJCZAQGWXBC-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
- QSQGFMKPTBYFTM-UHFFFAOYSA-N tri(butan-2-yloxy)-propan-2-ylsilane Chemical compound CCC(C)O[Si](OC(C)CC)(OC(C)CC)C(C)C QSQGFMKPTBYFTM-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
- NJLVRMVLOPLQPN-UHFFFAOYSA-N tri(propan-2-yloxy)-[2-tri(propan-2-yloxy)silylethyl]silane Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)CC[Si](OC(C)C)(OC(C)C)OC(C)C NJLVRMVLOPLQPN-UHFFFAOYSA-N 0.000 description 1
- JOACWTBFBZONEE-UHFFFAOYSA-N tri(propan-2-yloxy)-[3-tri(propan-2-yloxy)silylphenyl]silane Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)C1=CC=CC([Si](OC(C)C)(OC(C)C)OC(C)C)=C1 JOACWTBFBZONEE-UHFFFAOYSA-N 0.000 description 1
- YKPHUUXOOBMNKG-UHFFFAOYSA-N tri(propan-2-yloxy)-[4-tri(propan-2-yloxy)silylphenyl]silane Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)C1=CC=C([Si](OC(C)C)(OC(C)C)OC(C)C)C=C1 YKPHUUXOOBMNKG-UHFFFAOYSA-N 0.000 description 1
- LXVXAFIGRZCOFI-UHFFFAOYSA-N tri(propan-2-yloxy)-[tri(propan-2-yloxy)silylmethyl]silane Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)C[Si](OC(C)C)(OC(C)C)OC(C)C LXVXAFIGRZCOFI-UHFFFAOYSA-N 0.000 description 1
- DWZGQVYXDVZBBB-UHFFFAOYSA-N tributoxy(2-tributoxysilylethyl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)CC[Si](OCCCC)(OCCCC)OCCCC DWZGQVYXDVZBBB-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
- SGCFZHOZKKQIBU-UHFFFAOYSA-N tributoxy(ethenyl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)C=C SGCFZHOZKKQIBU-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
- LEZQEMOONYYJBM-UHFFFAOYSA-N tributoxy(propan-2-yl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)C(C)C LEZQEMOONYYJBM-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
- DHAWHVVWUNNONG-UHFFFAOYSA-M tributyl(methyl)azanium;bromide Chemical compound [Br-].CCCC[N+](C)(CCCC)CCCC DHAWHVVWUNNONG-UHFFFAOYSA-M 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-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
- BJDLPDPRMYAOCM-UHFFFAOYSA-N triethoxy(propan-2-yl)silane Chemical compound CCO[Si](OCC)(OCC)C(C)C BJDLPDPRMYAOCM-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
- LGROXJWYRXANBB-UHFFFAOYSA-N trimethoxy(propan-2-yl)silane Chemical compound CO[Si](OC)(OC)C(C)C LGROXJWYRXANBB-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
- FZGRTEYZSVFFSE-UHFFFAOYSA-L trimethyl(octadecyl)azanium dibromide Chemical compound [Br-].C(CCCCCCCCCCCCCCCCC)[N+](C)(C)C.[Br-].C(CCCCCCCCCCCCCCCCC)[N+](C)(C)C FZGRTEYZSVFFSE-UHFFFAOYSA-L 0.000 description 1
- FLXZVVQJJIGXRS-UHFFFAOYSA-M trimethyl(octadecyl)azanium;hydroxide Chemical compound [OH-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C FLXZVVQJJIGXRS-UHFFFAOYSA-M 0.000 description 1
- 238000006227 trimethylsilylation reaction Methods 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
- FNNJGIKXHZZGCV-UHFFFAOYSA-N triphenoxy(propan-2-yl)silane Chemical compound C=1C=CC=CC=1O[Si](OC=1C=CC=CC=1)(C(C)C)OC1=CC=CC=C1 FNNJGIKXHZZGCV-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
- BZIXIRYKSIMLOB-UHFFFAOYSA-N tripropoxy(tripropoxysilylmethyl)silane Chemical compound CCCO[Si](OCCC)(OCCC)C[Si](OCCC)(OCCC)OCCC BZIXIRYKSIMLOB-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
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- GBGOZMPAPWGNGR-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]-[2-[tris[(2-methylpropan-2-yl)oxy]silyl]ethyl]silane Chemical compound CC(C)(C)O[Si](OC(C)(C)C)(OC(C)(C)C)CC[Si](OC(C)(C)C)(OC(C)(C)C)OC(C)(C)C GBGOZMPAPWGNGR-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
- 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
- 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
- H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
- H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
- H01B3/46—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes silicones
-
- 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
- C08G77/48—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 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
- C08G77/50—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 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms by carbon linkages
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- 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
- C09D183/14—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 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02109—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates
- H01L21/02112—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer
- H01L21/02123—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer the material containing silicon
- H01L21/02126—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer the material containing silicon the material containing Si, O, and at least one of H, N, C, F, or other non-metal elements, e.g. SiOC, SiOC:H or SiONC
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02109—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates
- H01L21/02205—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates the layer being characterised by the precursor material for deposition
- H01L21/02208—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates the layer being characterised by the precursor material for deposition the precursor containing a compound comprising Si
- H01L21/02214—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates the layer being characterised by the precursor material for deposition the precursor containing a compound comprising Si the compound comprising silicon and oxygen
- H01L21/02216—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates the layer being characterised by the precursor material for deposition the precursor containing a compound comprising Si the compound comprising silicon and oxygen the compound being a molecule comprising at least one silicon-oxygen bond and the compound having hydrogen or an organic group attached to the silicon or oxygen, e.g. a siloxane
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02225—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer
- H01L21/0226—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process
- H01L21/02282—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process liquid deposition, e.g. spin-coating, sol-gel techniques, spray coating
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Formation Of Insulating Films (AREA)
- Silicon Polymers (AREA)
- Organic Insulating Materials (AREA)
- Paints Or Removers (AREA)
Description
(A)成分;下記一般式(1)で表される化合物および下記一般式(2)で表される化合物の群から選ばれた少なくとも1種のシラン化合物と、(B)成分;下記一般式(3)で表される構造を有するカルボシランとを加水分解縮合して得られた加水分解縮合物と、
有機溶媒と、
を含む。
R1 aSi(OR2)4−a ・・・・・(1)
(式中、R1は1価の有機基を示し、R2は1価の有機基を示し、aは1〜2の整数を示す。)
R3 b(R4O)3−bSi−(R7)d−Si(OR5)3−cR6 c ・・・(2)
(式中、R3〜R6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の数を示し、R7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は0または1を示す。)
(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、アリール基、アリル基、およびグリシジ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、アリール基、アリル基、およびグリシジ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、アリール基、アリル基、およびグリシジ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、置換または非置換のメチレン基、アルキレン基、アルケニレン基、アルキニレン基、アリーレン基を示し、e,f,gは、それぞれ0〜10,000の数を示し、10<e+f+g<10,000の条件を満たす。)
(X1X2X3X4N)hY ・・・・・(4)
(式中、X1,X2,X3,X4は同一または異なり、それぞれ水素原子、炭素数1〜20のアルキル基、ヒドロキシアルキル基、アリール基、およびアリールアルキル基からなる群より選ばれる基を示し、Yはハロゲン原子または1〜4価のアニオン性基を示し、hは1〜4の整数を示す。)
(A)成分;下記一般式(1)で表される化合物および下記一般式(2)で表される化合物の群から選ばれた少なくとも1種のシラン化合物と、(B)成分;下記一般式(3)で表される構造を有するカルボシランとを加水分解縮合する工程を含む。
R1 aSi(OR2)4−a ・・・・・(1)
(式中、R1は1価の有機基を示し、R2は1価の有機基を示し、aは1〜2の整数を示す。)
R3 b(R4O)3−bSi−(R7)d−Si(OR5)3−cR6 c ・・・(2)
(式中、R3〜R6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の数を示し、R7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は0または1を示す。)
(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、アリール基、アリル基、およびグリシジ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、アリール基、アリル基、およびグリシジ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、アリール基、アリル基、およびグリシジ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、置換または非置換のメチレン基、アルキレン基、アルケニレン基、アルキニレン基、アリーレン基を示し、e,f,gは、それぞれ0〜10,000の数を示し、10<e+f+g<10,000の条件を満たす。)
前記塗膜について、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種の硬化処理を行なう工程と、を含む。
本発明の一実施形態に係る膜形成用組成物(絶縁膜形成用組成物)は、(A)成分;下記一般式(1)で表される化合物および下記一般式(2)で表される化合物の群から選ばれた少なくとも1種のシラン化合物を、(B)成分;下記一般式(3)で表される構造を有するカルボシランの存在下で加水分解し、縮合した加水分解縮合物(以下、「特定加水分解縮合物」という)と、有機溶媒とを含む。すなわち、本発明の一実施形態に係る絶縁膜形成用組成物の製造方法は、(A)成分と、(B)成分とを加水分解縮合する工程を含む。以下、各成分について説明する。
(A)成分は、下記一般式(1)で表される化合物(以下、「化合物1」という)、下記一般式(2)で表される化合物(以下、「化合物2」という)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。(A)成分は、1つのケイ素原子が4つの酸素原子で置換された部位が存在しない。
R1 aSi(OR2)4−a ・・・・・(1)
(式中、R1は1価の有機基を示し、R2は1価の有機基を示し、aは1〜2の整数を示す。)
R3 b(R4O)3−bSi−(R7)d−Si(OR5)3−cR6 c ・・・(2)
(式中、R3〜R6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の数を示し、R7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は0または1を示す。)
前記一般式(1)において、R1,R2で表される1価の有機基としては、アルキル基、アルケニル基、アリール基などを挙げることができる。ここで、アルキル基としては、メチル基、エチル基、プロピル基、ブチル基などが挙げられ、好ましくは炭素数1〜5であり、これらのアルキル基は鎖状でも、分岐していてもよい。前記一般式(1)において、アルケニル基としては、ビニル基、アリル基などが挙げられる。また、前記一般式(1)において、アリール基としては、フェニル基、ナフチル基、メチルフェニル基、エチルフェニル基、クロロフェニル基、ブロモフェニル基、フルオロフェニル基などを挙げることができる。
一般式(2)において、R3〜R6の1価の有機基としては、前記一般式(1)においてR1,R2として例示した1価の有機基と同様の基を挙げることができる。
次に(B)成分について説明する。(B)成分は、下記一般式(3)で表される構造を有するポリカルボシラン(以下、「化合物3」という)である。(B)成分は、前記(A)成分と縮合して、Si−O−Si結合を形成することができる。
(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、アリール基、アリル基、およびグリシジ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、アリール基、アリル基、およびグリシジ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、アリール基、アリル基、およびグリシジ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、置換または非置換のメチレン基、アルキレン基、アルケニレン基、アルキニレン基、アリーレン基を示し、e,f,gは、それぞれ0〜10,000の数を示し、10<e+f+g<10,000の条件を満たす。)
ここで、前記加水分解縮合は、塩基性触媒、酸性触媒、または金属キレート触媒などの(C)触媒の存在下で行なわれることが好ましい。
前記膜形成用組成物に含まれる加水分解縮合物を製造する際、(C)触媒として塩基性触媒を使用することにより、得られる加水分解縮合物の分子構造に存在する分子鎖の分岐度を高くすることができ、かつ、その分子量をより大きくすることができる。これにより、上述した構造を有する加水分解縮合物を得ることができる。
(X1X2X3X4N)hY・・・・・(4)
(C)触媒として使用可能な酸性触媒としては、例えば、塩酸、硝酸、硫酸、フッ酸、リン酸、ホウ酸などの無機酸;
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。これらの酸性触媒は、1種あるいは2種以上を同時に使用してもよい。
(C)触媒として使用可能な金属キレート触媒としては、例えば、トリエトキシ・モノ(アセチルアセトナート)チタン、トリ−n−プロポキシ・モノ(アセチルアセトナート)チタン、トリ−i−プロポキシ・モノ(アセチルアセトナート)チタン、トリ−n−ブトキシ・モノ(アセチルアセトナート)チタン、トリ−sec−ブトキシ・モノ(アセチルアセトナート)チタン、トリ−t−ブトキシ・モノ(アセチルアセトナート)チタン、ジエトキシ・ビス(アセチルアセトナート)チタン、ジ−n−プロポキシ・ビス(アセチルアセトナート)チタン、ジ−i−プロポキシ・ビス(アセチルアセトナート)チタン、ジ−n−ブトキシ・ビス(アセチルアセトナート)チタン、ジ−sec−ブトキシ・ビス(アセチルアセトナート)チタン、ジ−t−ブトキシ・ビス(アセチルアセトナート)チタン、モノエトキシ・トリス(アセチルアセトナート)チタン、モノ−n−プロポキシ・トリス(アセチルアセトナート)チタン、モノ−i−プロポキシ・トリス(アセチルアセトナート)チタン、モノ−n−ブトキシ・トリス(アセチルアセトナート)チタン、モノ−sec−ブトキシ・トリス(アセチルアセトナート)チタン、モノ−t−ブトキシ・トリス(アセチルアセトナート)チタン、テトラキス(アセチルアセトナート)チタン、トリエトキシ・モノ(エチルアセトアセテート)チタン、トリ−n−プロポキシ・モノ(エチルアセトアセテート)チタン、トリ−i−プロポキシ・モノ(エチルアセトアセテート)チタン、トリ−n−ブトキシ・モノ(エチルアセトアセテート)チタン、トリ−sec−ブトキシ・モノ(エチルアセトアセテート)チタン、トリ−t−ブトキシ・モノ(エチルアセトアセテート)チタン、ジエトキシ・ビス(エチルアセトアセテート)チタン、ジ−n−プロポキシ・ビス(エチルアセトアセテート)チタン、ジ−i−プロポキシ・ビス(エチルアセトアセテート)チタン、ジ−n−ブトキシ・ビス(エチルアセトアセテート)チタン、ジ−sec−ブトキシ・ビス(エチルアセトアセテート)チタン、ジ−t−ブトキシ・ビス(エチルアセトアセテート)チタン、モノエトキシ・トリス(エチルアセトアセテート)チタン、モノ−n−プロポキシ・トリス(エチルアセトアセテート)チタン、モノ−i−プロポキシ・トリス(エチルアセトアセテート)チタン、モノ−n−ブトキシ・トリス(エチルアセトアセテート)チタン、モノ−sec−ブトキシ・トリス(エチルアセトアセテート)チタン、モノ−t−ブトキシ・トリス(エチルアセトアセテート)チタン、テトラキス(エチルアセトアセテート)チタン、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)チタン、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)チタン、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)チタンなどのチタンキレート化合物;
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良い。
上述したように、特定加水分解縮合物は、上記(A)成分と上記(B)成分とを加水分解縮合することにより得られる。
上記絶縁膜形成用組成物に含まれる有機溶媒としては、アルコール系溶媒、ケトン系溶媒、アミド系溶媒、エーテル系溶媒、エステル系溶媒、脂肪族炭化水素系溶媒、芳香族系溶媒および含ハロゲン溶媒の群から選ばれた少なくとも1種が挙げられる。
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。
前記絶縁膜形成用組成物には、さらに有機ポリマーや界面活性剤などの成分を添加してもよい。また、これらの添加物は、(A)成分および(B)成分を混合する前の各成分が溶解もしくは分散された溶剤中に添加されていてもよい。
有機ポリマーとしては、例えば、糖鎖構造を有する重合体、ビニルアミド系重合体、(メタ)アクリル系重合体、芳香族ビニル化合物系重合体、デンドリマー、ポリイミド,ポリアミック酸、ポリアリーレン、ポリアミド、ポリキノキサリン、ポリオキサジアゾール、フッ素系重合体、ポリアルキレンオキサイド構造を有する重合体などを挙げることができる。
−(X′)l−(Y′)m−
−(X′)l−(Y′)m−(X′)n−
(式中、X′は−CH2CH2O−で表される基を、Y′は−CH2CH(CH3)O−で表される基を示し、lは1〜90、mは10〜99、nは0〜90の数を示す。)
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、好ましくはフッ素系界面活性剤、シリコーン系界面活性剤を挙げることができる。
本発明の一実施形態に係る膜(絶縁膜)の形成方法は、膜形成用組成物を基材に塗布し、塗膜を形成する工程と、前記塗膜について、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種の硬化処理を行なう工程と、を含む。
本発明の一実施形態に係るシリカ系膜は、低誘電率であり、かつ表面平坦性に優れるため、LSI、システムLSI、DRAM、SDRAM、RDRAM、D−RDRAMなどの半導体素子用層間絶縁膜として特に優れており、かつ、エッチングストッパー膜、半導体素子の表面コート膜などの保護膜、多層レジストを用いた半導体作製工程の中間層、多層配線基板の層間絶縁膜、液晶表示素子用の保護膜や絶縁膜などに好適に用いることができる。本発明の一実施形態に係るシリカ系膜の比誘電率は通常3.5以下であり、1.8〜3.0であるのが好ましい。
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。
各種膜の評価は、次のようにして行った。
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法により当該膜の比誘電率を測定した。
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。
40℃で30日保存した膜形成用組成物を、スピンコート法を用いて基材に塗布し、ホットプレート上にて90℃で3分間、次いで窒素雰囲気下200℃で3分間基板を乾燥し、さらに50mTorrの減圧下にて420℃の縦型ファーネスで1時間焼成した。このようにして得られた塗膜の膜厚を、光学式膜厚計(Rudolph Technologies社製、Spectra Laser200)を用いて塗膜面内で50点測定した。得られた膜の膜厚を測定し、下式により求めた膜厚増加率により、保存安定性を評価した。
膜厚増加率(%)=((保存後の膜厚)−(保存前の膜厚))÷(保存前の膜厚)×100
A:膜厚増加率が4%以下である。
B:膜厚増加率が4%を超える。
シリカ系膜が形成された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、浸漬前後のシリカ系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。
残膜率(%)=(浸漬後の膜の膜厚)÷(浸漬前の膜の膜厚)×100
A:残膜率が99%以上である。
B:残膜率が99%未満である。
絶縁膜の断面を、集束イオンビーム法で観察用に加工し、TEMを用いて18000倍にて外観を調べた。判断結果を以下のようにして示す。
A:断面の形状観察では、均一な塗膜が得られている。
B:塗膜に海島状のドメイン相分離が確認される。
膜形成用組成物の29Si NMRスペクトル(100MHz)は、BRUKER AVANCE 500型を用いて測定された。
4.2.1.実施例1
コンデンサーを備えた石英製フラスコ中に、40%メチルアミン水溶液2.32g、超純水159.96g、およびエタノール464.97gを秤取り、60℃で攪拌した。次いで、メチルトリメトキシシラン56.83g、および下記一般式(5)で表される構造を有するポリカルボシラン(Mw=1,300)15.93gを加えた後、60℃で6時間攪拌し、ポリスチレン換算重量平均分子量39,000の加水分解縮合物を含む反応液を得た。反応液を室温に冷却後、プロピレングリコールモノプロピルエーテル613.24gおよび20%酢酸水溶液20.65gを加えた。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1を得た。この膜形成用組成物の29Si NMRスペクトル(100MHz)のスペクトルデータ(希釈溶媒:なし)は以下のとおりである。なお、本実施例および後述する実施例2〜4においては、29Si NMR測定において、50〜−80ppmに存在するピークの積分値の総和を1としたとき、−90〜−120ppmに存在するピークの積分値の総和が0.01未満であった。
-75 〜 -45 ppm (Broad), -30 〜 -10 ppm (Broad), 0 〜 20 ppm (Broad),
コンデンサーを備えた石英製フラスコ中に、20%水酸化テトラプロピルアンモニウム水溶液38.21g、超純水59.7g、およびイソプロパノール542.54gを秤取り、60℃で攪拌した。次いで、メチルトリメトキシシラン49.72g、および下記一般式(6)で表される構造を有する市販のポリカルボシラン(「NIPUSI Type-L」、日本カーボン株式会社から入手可能のポリジメチルシランのカルボシラン化ポリマー)(Mw=910)9.80gを加えた後、60℃で4時間攪拌し、ポリスチレン換算重量平均分子量48,000の加水分解縮合物を含む反応液を得た。反応液を室温に冷却後、プロピレングリコールモノプロピルエーテル552.03gおよび20%酢酸水溶液25.95gを加えた。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2を得た。この膜形成用組成物の29Si NMRスペクトル(100MHz)のスペクトルデータ(希釈溶媒:なし)は以下のとおりである。
-75 〜 -45 ppm (Broad), -40 〜 -30ppm(broad),-20 〜10ppm(broad),10〜30ppm(broad)
コンデンサーを備えた石英製フラスコ中に、25%水酸化テトラメチルアンモニウム水溶液4.92g、超純水93.5g、およびエタノール568.51gを秤取り、60℃で攪拌した。次いで、ジメチルジメトキシシラン8.21g、メチルトリメトキシシラン21.59g、および下記一般式(7)で表される構造を有するポリカルボシラン(Mw=1,050)3.14gを連続的に1時間かけて加えた後、さらに60℃で2時間攪拌し、ポリスチレン換算重量平均分子量34,000の加水分解縮合物を含む反応液を得た。反応液を室温に冷却後、プロピレングリコールモノプロピルエーテル658.76gおよび20%酢酸水溶液9.31gを加えた。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3を得た。この膜形成用組成物の29Si NMRスペクトル(100MHz)のスペクトルデータ(希釈溶媒:なし)は以下のとおりである。
-75 〜 -45 ppm (Broad), -30 〜 -10 ppm (Broad), 0 〜 20 ppm (Broad),
コンデンサーを備えた石英製フラスコ中に、10%シュウ酸水溶液13.44g、超純水41.72g、およびプロピレングリコールモノプロピルエーテル571.53gを秤取り、次いで、メチルトリメトキシシラン56.83g、および実施例1で用いたポリカルボシラン(Mw=1,300)15.93gを加えた後、60℃で2時間攪拌し、ポリスチレン換算重量平均分子量3,500の加水分解縮合物を含む反応液を得た。反応液を室温に冷却後、プロピレングリコールモノプロピルエーテル700.31gを加えた。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4を得た。この膜形成用組成物の29Si NMRスペクトル(100MHz)のスペクトルデータ(希釈溶媒:なし)は以下のとおりである。
-70 〜 -60 ppm (Broad), -60 〜 -50 ppm (Broad), -50 〜 -40 ppm (Broad), -30 〜 -10 ppm (Broad), 5 〜 10 ppm (Broad),
コンデンサーを備えた石英製フラスコ中に、40%メチルアミン水溶液2.58g、超純水178.16g、およびエタノール435.34gを秤取り、60℃で攪拌した。次いで、メチルトリメトキシシラン41.07g、テトラエトキシシラン26.92g、および下記一般式(8)で表される構造を有するポリカルボシラン(Mw=1,300)15.93gを加えた後、60℃で6時間攪拌し、ポリスチレン換算重量平均分子量45,000の加水分解縮合物を含む反応液を得た。反応液を室温に冷却後、プロピレングリコールモノプロピルエーテル613.50gおよび20%酢酸水溶液22.96gを加えた。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5を得た。この膜形成用組成物の29Si NMRスペクトル(100MHz)のスペクトルデータ(希釈溶媒:なし)は以下のとおりである。なお、本比較例および後述する比較例2〜4においては、29Si NMR測定において、50〜−80ppmに存在するピークの積分値の総和を1としたとき、−90〜−120ppmに存在するピークの積分値の総和が0.01より大きかった。
-115 〜 -90 ppm (Broad), -75 〜 -45 ppm (Broad), -30 〜 -10 ppm (Broad), 0 〜 20 ppm (Broad),
コンデンサーを備えた石英製フラスコ中に、20%水酸化テトラプロピルアンモニウム水溶液45.93g、超純水71.8g、およびイソプロパノール495.31gを秤取り、60℃で攪拌した。次いで、メチルトリメトキシシラン26.24g、テトラプロポキシシラン50.93g、および下記一般式(9)で表される構造を有する市販のポリカルボシラン(「NIPUSI Type-L」、日本カーボン株式会社から入手可能であるポリジメチルシランのカルボシラン化ポリマー)(Mw=910)9.80gを加えた後、60℃で4時間攪拌し、ポリスチレン換算重量平均分子量55,000の加水分解縮合物を含む反応液を得た。反応液を室温に冷却後、プロピレングリコールモノプロピルエーテル551.86gおよび20%酢酸水溶液31.20gを加えた。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6を得た。この膜形成用組成物の29Si NMRスペクトル(100MHz)のスペクトルデータ(希釈溶媒:なし)は以下のとおりである。
-115 〜 -90 ppm(Broad), -75 〜 -45 ppm (Broad), -40 〜 -30ppm(broad),-20 〜10ppm(br oad),10〜30ppm(broad)
コンデンサーを備えた石英製フラスコ中に、25%水酸化テトラメチルアンモニウム水溶液5.80g、超純水110.30g、およびエタノール548.08gを秤取り、60℃で攪拌した。次いで、ジメチルジメトキシシラン5.70g、メチルトリメトキシシラン16.15g、テトラメトキシシラン10.83g、および下記一般式(10)で表される構造を有するポリカルボシラン(Mw=1,050)3.14gを連続的に1時間かけて加えた後、さらに60℃で2時間攪拌し、ポリスチレン換算重量平均分子量40,000の加水分解縮合物を含む反応液を得た。反応液を室温に冷却後、プロピレングリコールモノプロピルエーテル658.38gおよび20%酢酸水溶液10.98gを加えた。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7を得た。この膜形成用組成物の29Si NMRスペクトル(100MHz)のスペクトルデータ(希釈溶媒:なし)は以下のとおりである。
-115 〜 -90 ppm (Broad), -75 〜 -45 ppm (Broad), -30 〜 -10 ppm (Broad), 0 〜 20 ppm (Broad),
コンデンサーを備えた石英製フラスコ中に、10%シュウ酸水溶液14.97g、超純水46.44g、およびプロピレングリコールモノプロピルエーテル554.25gを秤取り、次いでメチルトリメトキシシラン41.07g、テトラエトキシシラン26.92g、および実施例1で用いたものと同じポリカルボシラン(Mw=1,300)15.93gを加えた後、60℃で2時間攪拌し、ポリスチレン換算重量平均分子量3,700の加水分解縮合物を含む反応液を得た。反応液を室温に冷却後、プロピレングリコールモノプロピルエーテル700.16gを加えた。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8を得た。この膜形成用組成物の29Si NMRスペクトル(100MHz)のスペクトルデータ(希釈溶媒:なし)は以下のとおりである。
-110 〜 -95 ppm (Broad), -95 〜 -90 ppm (Broad), -90 〜 -80 ppm (Broad), -70 〜 -60 ppm (Broad), -60 〜 -50 ppm (Broad), -50 〜 -40 ppm (Broad), -30 〜 -10 ppm (Broad), 5 〜 10 ppm (Broad),
実施例1〜4および比較例1〜4で得られた膜形成用組成物1〜8を用いて、比誘電率、弾性率、硬度、薬液耐性、保存安定性および断面観察結果について評価を行った。なおその際に適用した硬化処理方法は表中に示したとおりである。評価結果を表1に示す。
Claims (13)
- (A)成分;下記一般式(1)で表される化合物および下記一般式(2)で表される化合物の群から選ばれた少なくとも1種のシラン化合物と、(B)成分;下記一般式(3)で表される構造を有するカルボシランと、を加水分解縮合して得られた加水分解縮合物と、
有機溶媒と、
を含む、絶縁膜形成用組成物。
R1 aSi(OR2)4−a ・・・・・(1)
(式中、R1はアルキル基、アルケニル基又はアリール基を示し、R2はアルキル基、アルケニル基又はアリール基を示し、aは1〜2の整数を示す。)
R3 b(R4O)3−bSi−(R7)d−Si(OR5)3−cR6 c ・・・(2)
(式中、R3〜R6は同一または異なり、それぞれアルキル基、アルケニル基又はアリール基を示し、bおよびcは同一または異なり、0〜2の数を示し、R7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は0または1を示す。)
(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、アリール基、アリル基、およびグリシジ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、アリール基、アリル基、およびグリシジ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、アリール基、アリル基、およびグリシジ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、置換または非置換のメチレン基、アルキレン基、アルケニレン基、アルキニレン基、アリーレン基を示し、e,f,gは、それぞれ0〜10,000の数を示し、10<e+f+g<10,000の条件を満たす。) - 請求項1において、
前記(A)成分は、前記一般式(1)で表される化合物からなる、絶縁膜形成用組成物。 - 請求項2において、
前記一般式(1)で表される化合物を少なくとも1種含み、
前記一般式(1)で表される化合物のうち、前記一般式(1)においてaが1である化合物の割合が50質量%以上である、絶縁膜形成用組成物。 - 請求項1ないし請求項3のいずれか一項において、
前記(A)成分を(A)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、前記(B)成分が1〜1000重量部である、絶縁膜形成用組成物。 - 請求項1ないし請求項4のいずれか一項において、
前記(B)成分のポリスチレン換算重量平均分子量が500〜10,000である、絶
縁膜形成用組成物。 - 請求項1ないし請求項5のいずれか一項において、
前記加水分解縮合は、塩基性触媒、酸性触媒、または金属キレート触媒の存在下で行なわれる、絶縁膜形成用組成物。 - 請求項6において、
前記加水分解縮合は、塩基性触媒の存在下で行なわれる、絶縁膜形成用組成物。 - 請求項7において、
前記塩基性触媒は、下記一般式(4)で表される含窒素化合物である、絶縁膜形成用組成物。
(X1X2X3X4N)hY ・・・・・(4)
(式中、X1,X2,X3,X4は同一または異なり、それぞれ水素原子、炭素数1〜20のアルキル基、ヒドロキシアルキル基、アリール基、およびアリールアルキル基からなる群より選ばれる基を示し、Yはハロゲン原子または1〜4価のアニオン性基を示し、hは1〜4の整数を示す。) - 請求項1ないし請求項8のいずれか一項において、
1つのケイ素原子が4つの酸素原子で置換された部位が存在しない、絶縁膜形成用組成物。 - (A)成分;下記一般式(1)で表される化合物および下記一般式(2)で表される化合物の群から選ばれた少なくとも1種のシラン化合物と、(B)成分;下記一般式(3)で表される構造を有するカルボシランと、を加水分解縮合する工程を含む、絶縁膜形成用組成物の製造方法。
R1 aSi(OR2)4−a ・・・・・(1)
(式中、R1はアルキル基、アルケニル基又はアリール基を示し、R2はアルキル基、アルケニル基又はアリール基を示し、aは1〜2の整数を示す。)
R3 b(R4O)3−bSi−(R7)d−Si(OR5)3−cR6 c ・・・(2)
(式中、R3〜R6は同一または異なり、それぞれアルキル基、アルケニル基又はアリール基を示し、bおよびcは同一または異なり、0〜2の数を示し、R7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は0または1を示す。)
(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、アリール基、アリル基、およびグリシジ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、アリール基、アリル基、およびグリシジ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、アリール基、アリル基、およびグリシジ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、置換または非置換のメチレン基、アルキレン基、アルケニレン基、アルキニレン基、アリーレン基を示し、e,f,gは、それぞれ0〜10,000の数を示し、10<e+f+g<10,000の条件を満たす。) - 請求項10に記載の製造方法によって得られる加水分解縮合ポリマー。
- 請求項1ないし請求項9のいずれか一項に記載の絶縁膜形成用組成物を基板に塗布し、塗膜を形成する工程と、
前記塗膜について、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種の硬化処理を行なう工程と、を含む、シリカ系絶縁膜の形成方法。 - 請求項12に記載のシリカ系絶縁膜の形成方法により得られる、シリカ系絶縁膜。
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