WO2009119583A1 - 化学気相成長法用材料ならびにケイ素含有絶縁膜およびその製造方法 - Google Patents
化学気相成長法用材料ならびにケイ素含有絶縁膜およびその製造方法 Download PDFInfo
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- WO2009119583A1 WO2009119583A1 PCT/JP2009/055825 JP2009055825W WO2009119583A1 WO 2009119583 A1 WO2009119583 A1 WO 2009119583A1 JP 2009055825 W JP2009055825 W JP 2009055825W WO 2009119583 A1 WO2009119583 A1 WO 2009119583A1
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- WO
- WIPO (PCT)
- Prior art keywords
- silicon
- insulating film
- vapor deposition
- chemical vapor
- added
- Prior art date
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- 239000000463 material Substances 0.000 title claims abstract description 71
- 238000005229 chemical vapour deposition Methods 0.000 title claims abstract description 63
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 title claims description 142
- 229910052710 silicon Inorganic materials 0.000 title claims description 134
- 239000010703 silicon Substances 0.000 title claims description 126
- 238000000034 method Methods 0.000 title claims description 33
- 238000004519 manufacturing process Methods 0.000 title claims description 22
- 230000008569 process Effects 0.000 title description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 27
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 26
- 239000001257 hydrogen Substances 0.000 claims abstract description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 18
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 12
- -1 organosilane compound Chemical class 0.000 claims description 93
- 239000000758 substrate Substances 0.000 claims description 38
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 31
- 239000001301 oxygen Substances 0.000 claims description 31
- 229910052760 oxygen Inorganic materials 0.000 claims description 31
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 27
- 239000003795 chemical substances by application Substances 0.000 claims description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- 229910052799 carbon Inorganic materials 0.000 claims description 23
- 238000010438 heat treatment Methods 0.000 claims description 16
- 239000011148 porous material Substances 0.000 claims description 15
- 238000011282 treatment Methods 0.000 claims description 6
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 238000010894 electron beam technology Methods 0.000 claims description 4
- 238000000151 deposition Methods 0.000 claims description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract 1
- 150000001282 organosilanes Chemical class 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 0.000 abstract 1
- 239000010408 film Substances 0.000 description 194
- 230000015572 biosynthetic process Effects 0.000 description 63
- 238000003786 synthesis reaction Methods 0.000 description 56
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 55
- 239000007789 gas Substances 0.000 description 45
- 238000006243 chemical reaction Methods 0.000 description 42
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 38
- 239000000243 solution Substances 0.000 description 38
- 238000003756 stirring Methods 0.000 description 38
- 150000001875 compounds Chemical class 0.000 description 36
- 238000001816 cooling Methods 0.000 description 29
- 239000000203 mixture Substances 0.000 description 28
- 239000011777 magnesium Substances 0.000 description 27
- 229910052749 magnesium Inorganic materials 0.000 description 27
- 239000000377 silicon dioxide Substances 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- 238000012545 processing Methods 0.000 description 22
- 229910052751 metal Inorganic materials 0.000 description 20
- 239000002184 metal Substances 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 20
- 239000012535 impurity Substances 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 229910052782 aluminium Inorganic materials 0.000 description 18
- 229910052802 copper Inorganic materials 0.000 description 17
- 239000010949 copper Substances 0.000 description 17
- 239000000126 substance Substances 0.000 description 17
- 238000004380 ashing Methods 0.000 description 16
- 229910052804 chromium Inorganic materials 0.000 description 16
- 230000000052 comparative effect Effects 0.000 description 16
- 238000001514 detection method Methods 0.000 description 16
- 238000004817 gas chromatography Methods 0.000 description 16
- 229910052745 lead Inorganic materials 0.000 description 16
- 229910052744 lithium Inorganic materials 0.000 description 16
- 229910052748 manganese Inorganic materials 0.000 description 16
- 229910052759 nickel Inorganic materials 0.000 description 16
- 229910052709 silver Inorganic materials 0.000 description 16
- 239000011734 sodium Substances 0.000 description 16
- 229910052718 tin Inorganic materials 0.000 description 16
- 229910052719 titanium Inorganic materials 0.000 description 16
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 16
- 229910052721 tungsten Inorganic materials 0.000 description 16
- 229910052725 zinc Inorganic materials 0.000 description 16
- 229910052726 zirconium Inorganic materials 0.000 description 16
- 238000004821 distillation Methods 0.000 description 15
- 239000012074 organic phase Substances 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 14
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- 239000012043 crude product Substances 0.000 description 14
- 239000011229 interlayer Substances 0.000 description 14
- 150000003839 salts Chemical class 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 11
- 239000004065 semiconductor Substances 0.000 description 11
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 10
- 125000003545 alkoxy group Chemical group 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- ZPILIIPBPKDNTR-UHFFFAOYSA-N dimethoxymethyl(dimethoxymethylsilylmethyl)silane Chemical compound COC(OC)[SiH2]C[SiH2]C(OC)OC ZPILIIPBPKDNTR-UHFFFAOYSA-N 0.000 description 9
- 125000005843 halogen group Chemical group 0.000 description 9
- 230000020169 heat generation Effects 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 238000011156 evaluation Methods 0.000 description 8
- 125000000962 organic group Chemical group 0.000 description 8
- 229910052697 platinum Inorganic materials 0.000 description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 235000019270 ammonium chloride Nutrition 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 229930195733 hydrocarbon Natural products 0.000 description 7
- 229960002050 hydrofluoric acid Drugs 0.000 description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- 238000010898 silica gel chromatography Methods 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- GJEZBVHHZQAEDB-UHFFFAOYSA-N 6-oxabicyclo[3.1.0]hexane Chemical compound C1CCC2OC21 GJEZBVHHZQAEDB-UHFFFAOYSA-N 0.000 description 6
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000012298 atmosphere Substances 0.000 description 6
- SSQOSTRUDOUBJZ-UHFFFAOYSA-N chloromethyl-methyl-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](CCl)(C)C1=CC=CC=C1 SSQOSTRUDOUBJZ-UHFFFAOYSA-N 0.000 description 6
- NBBQQQJUOYRZCA-UHFFFAOYSA-N diethoxymethylsilane Chemical compound CCOC([SiH3])OCC NBBQQQJUOYRZCA-UHFFFAOYSA-N 0.000 description 6
- 238000001020 plasma etching Methods 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 125000001153 fluoro group Chemical group F* 0.000 description 5
- 238000004508 fractional distillation Methods 0.000 description 5
- 238000000623 plasma-assisted chemical vapour deposition Methods 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 4
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 4
- 125000004430 oxygen atom Chemical group O* 0.000 description 4
- 238000005268 plasma chemical vapour deposition Methods 0.000 description 4
- 229910000077 silane Inorganic materials 0.000 description 4
- 150000004756 silanes Chemical class 0.000 description 4
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 4
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 3
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- 238000009835 boiling Methods 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- MNKYQPOFRKPUAE-UHFFFAOYSA-N chloro(triphenyl)silane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 MNKYQPOFRKPUAE-UHFFFAOYSA-N 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 229940126214 compound 3 Drugs 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- PFMKUUJQLUQKHT-UHFFFAOYSA-N dichloro(ethyl)silicon Chemical compound CC[Si](Cl)Cl PFMKUUJQLUQKHT-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 238000007654 immersion Methods 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- KAJRUHJCBCZULP-UHFFFAOYSA-N 1-cyclohepta-1,3-dien-1-ylcyclohepta-1,3-diene Chemical compound C1CCC=CC=C1C1=CC=CCCC1 KAJRUHJCBCZULP-UHFFFAOYSA-N 0.000 description 2
- GRYZOUWILMZVFC-UHFFFAOYSA-N 2,2-dichloroethenyl(2,2-dichloroethenylsilylmethyl)silane Chemical compound ClC(Cl)=C[SiH2]C[SiH2]C=C(Cl)Cl GRYZOUWILMZVFC-UHFFFAOYSA-N 0.000 description 2
- AYSVQOBDSOZXHW-UHFFFAOYSA-N 2,2-diethoxyethyl-[2-(2,2-diethoxyethylsilyl)ethynyl]silane Chemical group C(C)OC(C[SiH2]C#C[SiH2]CC(OCC)OCC)OCC AYSVQOBDSOZXHW-UHFFFAOYSA-N 0.000 description 2
- VEKVBCMENLOUJU-UHFFFAOYSA-N 2,2-dimethoxyethenyl(2,2-dimethoxyethenylsilylmethyl)silane Chemical compound COC(=C[SiH2]C[SiH2]C=C(OC)OC)OC VEKVBCMENLOUJU-UHFFFAOYSA-N 0.000 description 2
- RBCWMGQUZQBQII-UHFFFAOYSA-N 2,2-diphenylethenyl(2,2-diphenylethenylsilylmethyl)silane Chemical compound C1(=CC=CC=C1)C(=C[SiH2]C[SiH2]C=C(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1 RBCWMGQUZQBQII-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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- NWALBCJWTONTBG-UHFFFAOYSA-N C=1C=CC=CC=1C(C=1C=CC=CC=1)[SiH2]C[SiH2]C(C=1C=CC=CC=1)C1=CC=CC=C1 Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)[SiH2]C[SiH2]C(C=1C=CC=CC=1)C1=CC=CC=C1 NWALBCJWTONTBG-UHFFFAOYSA-N 0.000 description 2
- KLKMUGZQOUDWLX-UHFFFAOYSA-N CCOC(OCC)C[SiH2]CC[SiH2]CC(OCC)OCC Chemical compound CCOC(OCC)C[SiH2]CC[SiH2]CC(OCC)OCC KLKMUGZQOUDWLX-UHFFFAOYSA-N 0.000 description 2
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
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- 125000003118 aryl group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- OHZLMJKQTSHYJH-UHFFFAOYSA-N bis(ethenyl)-methoxy-(trimethoxysilylmethyl)silane Chemical compound CO[Si](OC)(OC)C[Si](OC)(C=C)C=C OHZLMJKQTSHYJH-UHFFFAOYSA-N 0.000 description 2
- GIMNVVYNZAESTJ-UHFFFAOYSA-N bis(ethenyl)-methyl-(trimethoxysilylmethyl)silane Chemical compound CO[Si](OC)(OC)C[Si](C)(C=C)C=C GIMNVVYNZAESTJ-UHFFFAOYSA-N 0.000 description 2
- QJANOUWJPHKGQA-UHFFFAOYSA-N bis(ethenyl)-phenyl-(triphenylsilylmethyl)silane Chemical compound C=1C=CC=CC=1[Si](C=C)(C=C)C[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 QJANOUWJPHKGQA-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- OJZNZOXALZKPEA-UHFFFAOYSA-N chloro-methyl-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](Cl)(C)C1=CC=CC=C1 OJZNZOXALZKPEA-UHFFFAOYSA-N 0.000 description 2
- GLBJEGJIZHKUOI-UHFFFAOYSA-N chloromethyl(2,2-diphenylethenyl)silane Chemical compound ClC[SiH2]C=C(C1=CC=CC=C1)C1=CC=CC=C1 GLBJEGJIZHKUOI-UHFFFAOYSA-N 0.000 description 2
- OOCUOKHIVGWCTJ-UHFFFAOYSA-N chloromethyl(trimethyl)silane Chemical compound C[Si](C)(C)CCl OOCUOKHIVGWCTJ-UHFFFAOYSA-N 0.000 description 2
- JOEJYLLWXYGKID-UHFFFAOYSA-N chloromethyl-bis(ethenyl)-methylsilane Chemical compound ClC[Si](C)(C=C)C=C JOEJYLLWXYGKID-UHFFFAOYSA-N 0.000 description 2
- AGSAAEUUKGRHHV-UHFFFAOYSA-N chloromethyl-ethenyl-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](C=C)(CCl)C1=CC=CC=C1 AGSAAEUUKGRHHV-UHFFFAOYSA-N 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 2
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- AGHOFQMBOFGNOZ-UHFFFAOYSA-N dichloromethyl(dichloromethylsilylmethyl)silane Chemical compound ClC(Cl)[SiH2]C[SiH2]C(Cl)Cl AGHOFQMBOFGNOZ-UHFFFAOYSA-N 0.000 description 2
- JNRPFXHBIIJBLN-UHFFFAOYSA-N diethoxy-[2-[ethoxy(diethyl)silyl]ethyl]-ethylsilane Chemical compound CCO[Si](CC)(CC)CC[Si](CC)(OCC)OCC JNRPFXHBIIJBLN-UHFFFAOYSA-N 0.000 description 2
- RSKSVHNEOWXAMY-UHFFFAOYSA-N dimethoxy-[[methoxy(dimethyl)silyl]methyl]-methylsilane Chemical compound CO[Si](C)(C)C[Si](C)(OC)OC RSKSVHNEOWXAMY-UHFFFAOYSA-N 0.000 description 2
- CUQYKZJZQKOBRN-UHFFFAOYSA-N dimethoxy-methyl-(trimethoxysilylmethyl)silane Chemical compound CO[Si](C)(OC)C[Si](OC)(OC)OC CUQYKZJZQKOBRN-UHFFFAOYSA-N 0.000 description 2
- KFFCPURJWSJKMB-UHFFFAOYSA-N dimethoxy-methyl-(trimethylsilylmethyl)silane Chemical compound CO[Si](C)(OC)C[Si](C)(C)C KFFCPURJWSJKMB-UHFFFAOYSA-N 0.000 description 2
- LIJGEAYWEYERTL-UHFFFAOYSA-N dimethoxysilylmethyl(dimethoxy)silane Chemical compound CO[SiH](OC)C[SiH](OC)OC LIJGEAYWEYERTL-UHFFFAOYSA-N 0.000 description 2
- KWDFAYVNQUZZCG-UHFFFAOYSA-N dimethoxysilylmethyl-dimethoxy-methylsilane Chemical compound CO[SiH](OC)C[Si](C)(OC)OC KWDFAYVNQUZZCG-UHFFFAOYSA-N 0.000 description 2
- MPTMUDKLAKGNMJ-UHFFFAOYSA-N dimethyl-[[methyl(diphenyl)silyl]methyl]-phenylsilane Chemical compound C=1C=CC=CC=1[Si](C)(C)C[Si](C)(C=1C=CC=CC=1)C1=CC=CC=C1 MPTMUDKLAKGNMJ-UHFFFAOYSA-N 0.000 description 2
- UIPCTBJSETXEKY-UHFFFAOYSA-N diphenylsilylmethyl-methyl-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(C)C[SiH](C=1C=CC=CC=1)C1=CC=CC=C1 UIPCTBJSETXEKY-UHFFFAOYSA-N 0.000 description 2
- MAEGCNQCZAFBGZ-UHFFFAOYSA-N ethenyl-dimethoxy-(trimethoxysilylmethyl)silane Chemical compound CO[Si](OC)(OC)C[Si](OC)(OC)C=C MAEGCNQCZAFBGZ-UHFFFAOYSA-N 0.000 description 2
- ZVJARKGKPSGYBK-UHFFFAOYSA-N ethenyl-diphenyl-(triphenylsilylmethyl)silane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(C=C)C[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 ZVJARKGKPSGYBK-UHFFFAOYSA-N 0.000 description 2
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- XKINWJBZPLWKCW-UHFFFAOYSA-N methoxy-[methoxy(dimethyl)silyl]oxy-dimethylsilane Chemical compound CO[Si](C)(C)O[Si](C)(C)OC XKINWJBZPLWKCW-UHFFFAOYSA-N 0.000 description 2
- ANXQIGQINRJEEI-UHFFFAOYSA-N methyl-diphenyl-(triphenylsilylmethyl)silane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(C)C[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 ANXQIGQINRJEEI-UHFFFAOYSA-N 0.000 description 2
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- GGDJDBDYFMWWFL-UHFFFAOYSA-N trichloro-[[dichloro(ethenyl)silyl]methyl]silane Chemical compound Cl[Si](Cl)(Cl)C[Si](Cl)(Cl)C=C GGDJDBDYFMWWFL-UHFFFAOYSA-N 0.000 description 2
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 2
- 239000005052 trichlorosilane Substances 0.000 description 2
- KASQZVXNRJUHJI-UHFFFAOYSA-N triethoxy-[2-[ethoxy(ethyl)silyl]ethyl]silane Chemical compound CCO[SiH](CC)CC[Si](OCC)(OCC)OCC KASQZVXNRJUHJI-UHFFFAOYSA-N 0.000 description 2
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- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- LMQGXNPPTQOGDG-UHFFFAOYSA-N trimethoxy(trimethoxysilyl)silane Chemical compound CO[Si](OC)(OC)[Si](OC)(OC)OC LMQGXNPPTQOGDG-UHFFFAOYSA-N 0.000 description 1
- DJYGUVIGOGFJOF-UHFFFAOYSA-N trimethoxy(trimethoxysilylmethyl)silane Chemical compound CO[Si](OC)(OC)C[Si](OC)(OC)OC DJYGUVIGOGFJOF-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- XOAJIYVOSJHEQB-UHFFFAOYSA-N trimethyl trimethoxysilyl silicate Chemical compound CO[Si](OC)(OC)O[Si](OC)(OC)OC XOAJIYVOSJHEQB-UHFFFAOYSA-N 0.000 description 1
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
- PTUUTGJMRQWABQ-UHFFFAOYSA-N triphenyl(phenylsilyloxy)silane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)O[SiH2]C1=CC=CC=C1 PTUUTGJMRQWABQ-UHFFFAOYSA-N 0.000 description 1
- YMCDISDNGWJEGJ-UHFFFAOYSA-N triphenyl(propoxy)silane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(OCCC)C1=CC=CC=C1 YMCDISDNGWJEGJ-UHFFFAOYSA-N 0.000 description 1
- AKQNYQDSIDKVJZ-UHFFFAOYSA-N triphenylsilane Chemical compound C1=CC=CC=C1[SiH](C=1C=CC=CC=1)C1=CC=CC=C1 AKQNYQDSIDKVJZ-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 239000006200 vaporizer Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
- C23C16/00—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes
- C23C16/22—Chemical coating by decomposition of gaseous compounds, without leaving reaction products of surface material in the coating, i.e. chemical vapour deposition [CVD] processes characterised by the deposition of inorganic material, other than metallic material
- C23C16/30—Deposition of compounds, mixtures or solid solutions, e.g. borides, carbides, nitrides
- C23C16/40—Oxides
- C23C16/401—Oxides containing silicon
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02109—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates
- H01L21/02112—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer
- H01L21/02123—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer the material containing silicon
- H01L21/02126—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer the material containing silicon the material containing Si, O, and at least one of H, N, C, F, or other non-metal elements, e.g. SiOC, SiOC:H or SiONC
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- 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
- H01L21/02203—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 porous
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02109—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates
- H01L21/02205—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
- H01L21/02211—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 being a silane, e.g. disilane, methylsilane or chlorosilane
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- 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
- H01L21/02263—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process deposition from the gas or vapour phase
- H01L21/02271—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process deposition from the gas or vapour phase deposition by decomposition or reaction of gaseous or vapour phase compounds, i.e. chemical vapour deposition
- H01L21/02274—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process deposition from the gas or vapour phase deposition by decomposition or reaction of gaseous or vapour phase compounds, i.e. chemical vapour deposition in the presence of a plasma [PECVD]
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- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
- H01L21/31—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to form insulating layers thereon, e.g. for masking or by using photolithographic techniques; After treatment of these layers; Selection of materials for these layers
- H01L21/314—Inorganic layers
- H01L21/316—Inorganic layers composed of oxides or glassy oxides or oxide based glass
- H01L21/31604—Deposition from a gas or vapour
- H01L21/31633—Deposition of carbon doped silicon oxide, e.g. SiOC
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- H—ELECTRICITY
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- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
- H01L21/31—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to form insulating layers thereon, e.g. for masking or by using photolithographic techniques; After treatment of these layers; Selection of materials for these layers
- H01L21/314—Inorganic layers
- H01L21/316—Inorganic layers composed of oxides or glassy oxides or oxide based glass
- H01L21/31695—Deposition of porous oxides or porous glassy oxides or oxide based porous glass
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02109—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates
- H01L21/02205—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
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/52—Arrangements for conducting electric current within the device in operation from one component to another, i.e. interconnections, e.g. wires, lead frames
- H01L23/522—Arrangements for conducting electric current within the device in operation from one component to another, i.e. interconnections, e.g. wires, lead frames including external interconnections consisting of a multilayer structure of conductive and insulating layers inseparably formed on the semiconductor body
- H01L23/532—Arrangements for conducting electric current within the device in operation from one component to another, i.e. interconnections, e.g. wires, lead frames including external interconnections consisting of a multilayer structure of conductive and insulating layers inseparably formed on the semiconductor body characterised by the materials
- H01L23/5329—Insulating materials
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/0001—Technical content checked by a classifier
- H01L2924/0002—Not covered by any one of groups H01L24/00, H01L24/00 and H01L2224/00
Definitions
- the present invention relates to a material for chemical vapor deposition, a silicon-containing insulating film, and a method for manufacturing the same.
- ULSI large-scale semiconductor integrated circuits
- the speeding up of ULSI has been realized by miniaturization and high integration of elements in a chip and multilayering of films.
- wiring resistance and inter-wiring parasitic capacitance increase, and wiring delay is becoming a dominant factor in signal delay of the entire device.
- introduction of a low resistivity wiring material or a low dielectric constant (Low-k) interlayer insulating film material is an essential technique.
- Examples of the low dielectric constant interlayer insulating film include inorganic interlayer insulating films such as a porous silica film having a reduced silica (SiO 2 ) film density, FSG which is a silica film doped with F, and a SiOC film doped with C.
- examples thereof include an organic interlayer insulating film such as a film, polyimide, polyarylene, and polyarylene ether. Since many of the widely used interlayer insulating films are formed by chemical vapor deposition (CVD), many proposals have been made by chemical vapor deposition. In particular, many silane compounds used for the reaction have been proposed. For example, those using dialkoxysilane (Japanese Patent Laid-Open Nos. 11-288931 and 2002-329718) have been proposed. By using such a material, a film having a low dielectric constant and sufficient adhesion with a barrier metal or the like is obtained.
- CVD chemical vapor deposition
- silane compounds are chemically stable, they require extreme conditions during film formation by chemical vapor deposition, and on the contrary, they are chemically unstable and are supplied into the chamber. There are those that cause a reaction in the piping and those that have poor storage stability of the silane compound itself.
- the insulating film after film formation has a high hygroscopic property, which causes a problem of increasing the leakage current.
- RIE Reactive Ion Etching
- JP-A-2007-318067 discloses that a compound in which two silicon atoms are bonded via a carbon chain and both silicon atoms are substituted with an alkoxy group is used for the above purpose. Yes.
- JP-A-2007-318067 discloses only an example in which two silicon atoms are bonded via a vinylene group, and such a compound has the aforementioned processing resistance. There is a concern that it is not necessarily excellent.
- the present applicant is a compound in which two silicon atoms are bonded via a carbon chain, and only one monovalent hydrocarbon group is bonded to one silicon atom, and the other silicon atom is bonded to the other silicon atom.
- a film having excellent processing resistance can be obtained when an atom is bonded to one or two alkoxy groups (International Publication WO2008 / 020593).
- the mechanical strength of the obtained film is insufficient, and development of an interlayer insulating film having further improved strength and processing resistance is demanded.
- the present invention provides a silicon-containing insulating film having a low relative dielectric constant, high work resistance, and excellent mechanical strength, a method for producing the same, and a material for chemical vapor deposition that can form the insulating film. .
- the inventors of the present invention have a silicon-carbon-silicon skeleton, and an organic silane compound having a specific structure in which oxygen is bonded to any one of the silicons is suitable for chemical vapor deposition while being chemically stable. Furthermore, it has been found that by using this organosilane compound, an interlayer insulating film material having a low relative dielectric constant, low hygroscopicity, and high processing resistance can be formed.
- the chemical vapor deposition material according to one embodiment of the present invention includes an organosilane compound represented by the following general formula (1).
- R 1 and R 2 are the same or different and each represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a vinyl group or a phenyl group, and R 3 and R 4 are the same or different and have 1 to 4 carbon atoms
- n 1.
- the above chemical vapor deposition material can be used to form an insulating film containing silicon, carbon, oxygen, and hydrogen.
- the content of elements other than silicon, carbon, oxygen, and hydrogen can be less than 10 ppb, and the moisture content can be less than 0.1%.
- a silicon-containing insulating film according to another embodiment of the present invention is formed by a chemical vapor deposition method using the above-mentioned chemical vapor deposition method material.
- the method for producing a silicon-containing insulating film according to another aspect of the present invention includes: Depositing the chemical vapor deposition material on a substrate by chemical vapor deposition to form a deposited film; A step of performing at least one curing treatment selected from heating, electron beam irradiation, ultraviolet irradiation, and oxygen plasma on the deposited film; including.
- the method for producing a silicon-containing insulating film includes a step of forming the deposited film by supplying the chemical vapor deposition method material and the pore forming agent to the substrate by the chemical vapor deposition method.
- a silicon-containing insulating film according to another embodiment of the present invention is obtained by the above-described method for producing a silicon-containing insulating film.
- the silicon-containing insulating film can include a —Si— (CH 2 ) n —Si—O— moiety (where n represents an integer of 1 to 3).
- the silicon-containing insulating film may have a relative dielectric constant of 3.0 or less.
- the chemical vapor deposition material can be suitably used in a semiconductor element or the like for which high integration and multilayering are desired, It is most suitable for chemical vapor deposition and can be used to form an insulating film having excellent mechanical strength, low relative dielectric constant, low hygroscopicity, and high processing resistance.
- the R 1 m —Si— (CH 2 ) n —Si—R 2 m ′ portion of the organosilane compound represented by the general formula (1) is less damaged by RIE.
- it functions as a function to increase resistance to a fluoric acid-based chemical
- the —Si— (OR 3 ) 3-m portion and the —Si— (OR 4 ) 3-m ′ portion are —Si—O—Si— It is presumed that an insulating film having excellent mechanical strength, a low relative dielectric constant and high processing resistance can be obtained because a bond is formed and a skeleton having a high degree of cross-linking is formed.
- the silicon-containing insulating film is excellent in mechanical strength, has a low relative dielectric constant and high processing resistance.
- an insulating film having excellent mechanical strength, a low relative dielectric constant, and high processing resistance can be obtained.
- the chemical vapor deposition material according to an embodiment of the present invention includes an organosilane compound (hereinafter also referred to as “compound 1”) represented by the following general formula (1).
- R 1 and R 2 are the same or different and each represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a vinyl group or a phenyl group, and R 3 and R 4 are the same or different and have 1 to 4 carbon atoms
- R 1 and R 2 are the same or different and each represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a vinyl group, or a phenyl group.
- examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, and a tert-butyl group.
- R 1 and R 2 are particularly preferably a methyl group, a vinyl group, or a hydrogen atom.
- R 3 and R 4 are the same or different and each represents an alkyl group having 1 to 4 carbon atoms, an acetyl group, or a phenyl group.
- examples of the alkyl group having 1 to 4 carbon atoms include the same alkyl groups as those exemplified as R 1 and R 2 above.
- R 3 and R 4 are particularly preferably a methyl group or an ethyl group.
- R 3 and R 4 are preferably the same.
- the total number of hydrogen atoms in R 1 and R 2 is 0 to 2 from the viewpoint of ease of synthesis and purification and ease of handling. Preferably, it is 0 to 1. From the viewpoint of lowering the boiling point of the organosilane compound and improving the mechanical strength of the formed silicon-containing film, the total number of hydrogen atoms in R 1 and R 2 is preferably 1 or 2.
- Case (ii) The insulating film obtained using the organosilane compound of case (ii) has very good mechanical strength, and has a low dielectric constant and high processing resistance.
- the organosilane compound represented by the general formula (1) the —Si— (OR 3 ) 3 moiety and the —Si— (OR 4 ) 2 moiety are —Si—.
- O—Si— bond is formed to form a three-dimensional skeleton having a high degree of cross-linking, and this skeleton contributes to the mechanical strength, and the —Si— (CH 2 ) n —Si—R 2 moiety Is expected to weaken the damage received from RIE and increase the resistance to fluoric acid chemicals.
- R 1 is a hydrogen atom.
- R 1 is more preferably a group other than a hydrogen atom from the viewpoint of ease of synthesis and purification and ease of handling.
- the organosilane compound represented by the general formula (1) includes only two substituents of one silicon atom or two substituents of one silicon atom and the other.
- One substituent of a silicon atom is substituted with any one of a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a vinyl group, and a phenyl group, and an oxygen atom is one substituent of one silicon atom and the other silicon It is bonded to two or three substituents of the atom.
- the organosilane compound of case (iii) the detailed mechanism is not clear, but the R 1 2 —Si— (CH 2 ) n —Si moiety of the organosilane compound represented by the general formula (1) is It acts as a function to reduce the damage received from RIE and increase the resistance to fluoric acid chemicals, and the —Si—OR 2 moiety and —Si— (OR 4 ) m moiety have —Si—O—Si— bonds.
- an insulating film having excellent mechanical strength, low dielectric constant and high processing resistance can be obtained by using the organosilane compound of case (iii) It is estimated that
- m is preferably 3 in that a film with better mechanical strength can be obtained.
- the total number of hydrogen atoms in R 1 and R 3 is 0 to 0 in terms of ease of synthesis and purification, and ease of handling. 2 is preferable, and 0 to 1 is more preferable. In view of lowering the boiling point of the organosilane compound and improving the mechanical strength of the formed film, the total number of hydrogen atoms in R 1 and R 3 is preferably 1 or 2.
- the chemical vapor deposition material according to the present embodiment is preferably mainly composed of the organosilane compound represented by the general formula (1), but may contain other components.
- the chemical vapor deposition material according to this embodiment preferably contains 30 to 100% of the organosilane compound represented by the general formula (1).
- the chemical vapor deposition material according to the present embodiment can be used to form an insulating film containing silicon, carbon, oxygen, and hydrogen.
- Such an insulating film is characterized by high resistance to processing because it has high resistance to a hydrofluoric acid chemical solution widely used in a cleaning process during a semiconductor manufacturing process.
- the chemical vapor deposition material according to the present embodiment contains the organosilane compound represented by the general formula (1), but when used as an insulating film forming material, silicon, carbon It is preferable that the content of elements other than oxygen, oxygen, and hydrogen (hereinafter also referred to as “impurities”) is less than 10 ppb and the moisture content is less than 0.1%.
- impurities elements other than oxygen, oxygen, and hydrogen
- a material for chemical vapor deposition according to an embodiment of the present invention includes a silane compound represented by the following general formula (2) (hereinafter also referred to as “compound 2”), and the following general formula (3). ) Represented by the following formula (4) and at least one selected from a silane compound represented by the following general formula (4) (hereinafter also referred to as “compound 4”). Silane compounds (hereinafter also referred to as “component (II)”). As for compounds 2 to 4, one or two or more may be used simultaneously.
- the chemical vapor deposition material according to one embodiment of the present invention can further include a pore forming agent described later together with the component (II).
- R 13 and R 14 are the same or different and each represents a hydrogen atom, a fluorine atom, or a monovalent organic group, and R 15 represents an oxygen atom, a phenylene group or — (CH 2 ) n —.
- the chemical vapor deposition material according to this embodiment includes the component (II), the molar ratio of the compound 1 (hereinafter also referred to as “component (I)”) and the component (II) is the component (I).
- component (I) the molar ratio of the compound 1 (hereinafter also referred to as “component (I)”) and the component (II) is the component (I).
- the component (I) is 10 mol% to 90 mol%, more preferably 15 mol% to 85 mol%.
- the chemical vapor deposition material according to this embodiment includes a pore forming agent, from the viewpoint of reducing the relative dielectric constant and obtaining a uniform film, 0.05 to about 100 parts by weight of component (I) It preferably contains 10,000 parts by weight of a pore-forming agent, more preferably 0.1 to 5000 parts by weight of a pore-forming agent.
- the molar ratio of the component (I) to the component (II) is (I) when the sum of the components (I) and (II) is 100 mol%. )
- Component is 10 mol% to 90 mol%, more preferably 15 mol% to 85 mol%.
- composition material for chemical vapor deposition
- the composition contains compound 1, it can be used to form an insulating film containing silicon, carbon, oxygen, and hydrogen.
- Such an insulating film is characterized by high resistance to processing because it has high resistance to a hydrofluoric acid chemical solution widely used in a cleaning process during a semiconductor manufacturing process.
- composition (chemical vapor deposition material) according to the second embodiment further contains at least one selected from compounds 2 to 4 having more crosslinkable substituents than compound 1. Therefore, by using such a composition, it is possible to form an insulating film having excellent mechanical strength and a low relative dielectric constant.
- examples of the monovalent organic group represented by R 6 and R 7 include an alkyl group, an alkenyl group, an aryl group, an allyl group, and a glycidyl group. Especially, it is preferable that the monovalent organic group represented by R 6 and R 7 is an alkyl group or a phenyl group.
- examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, and the like, preferably having 1 to 5 carbon atoms. These alkyl groups may be linear or branched, Further, a hydrogen atom may be substituted with a fluorine atom or the like.
- examples of the aryl group include a phenyl group, a naphthyl group, a methylphenyl group, an ethylphenyl group, a chlorophenyl group, a bromophenyl group, and a fluorophenyl group.
- examples of the alkenyl group include a vinyl group, a propenyl group, a 3-butenyl group, a 3-pentenyl group, and a 3-hexenyl group.
- compound 2 examples include tetramethoxysilane, tetraethoxysilane, trimethoxysilane, triethoxysilane, methyltrimethoxysilane, methyltriethoxysilane, methyltri-n-propoxysilane, methyltri-iso-propoxysilane, ethyltri Methoxysilane, ethyltriethoxysilane, phenyltrimethoxysilane, phenyltriethoxysilane, methyldimethoxysilane, methyldiethoxysilane, dimethyldimethoxysilane, dimethyldiethoxysilane, diethyldimethoxysilane, diethyldiethoxysilane, diphenyldimethoxysilane, diphenyl Diethoxysilane, dimethylmethoxysilane, dimethylethoxysilane, trimethylmethoxysilane, trimethylethoxys
- examples of the monovalent organic group represented by R 8 to R 11 include the same groups as those exemplified as R 6 and R 7 in the general formula (2).
- the compound 3 include, for example, hexamethoxydisilane, hexaethoxydisilane, 1,1,2,2-tetramethoxy-1,2-dimethyldisilane, 1,1,2,2-tetraethoxy-1,2- Dimethyldisilane, 1,1,2,2-tetramethoxy-1,2-diphenyldisilane, 1,2-dimethoxy-1,1,2,2-tetramethyldisilane, 1,2-diethoxy-1,1,2 , 2-tetramethyldisilane, 1,2-dimethoxy-1,1,2,2-tetraphenyldisilane, 1,1,3,3-tetramethyl-1,3-dimethoxydisiloxane, 1,1,3,3- Tetramethoxy-1,3-dimethyldisiloxane, hexamethyldisiloxane, hexamethoxydisiloxane, hexaethoxydisiloxane, 1,1,3,3-tty
- the compound 3 described above may be used alone or in combination of two or more.
- the compound 4 according to the present embodiment is an oligomer having a repeating structure represented by the general formula (4) and may have a cyclic structure.
- examples of the monovalent organic group represented by R 13 and R 14 include the same groups as those exemplified as R 6 and R 7 in the general formula (2).
- the compound 4 includes octamethyltrisilane, octaethyltrisilane, 1,2,3-trimethoxy-1,1,2,3,3-pentamethyltrisilane, 1,2, 3-trimethoxy-1,1,2,3,3-pentaethyltrisilane, octamethoxytrisilane, octaethoxytrisilane, 1,3,5,7-tetramethylcyclotetrasiloxane, 1,1,3,3 5,5,7,7-octamethylcyclotetrasiloxane can be mentioned as a preferred example.
- the compound 4 described above may be used alone or in combination of two or more.
- the method for producing the organosilane compound represented by the general formula (1) is not particularly limited, and examples thereof include the following first and second methods.
- the first method is a method in which an organosilane compound represented by the following general formula (5) and an organosilane compound represented by the following general formula (6) are subjected to a coupling reaction in the presence of a metal, and then halogenated. It is a method in which a hydrogen group is reacted to substitute a phenyl group with a halogen atom, and then the halogen atom is substituted with an alkoxy group using trialkyl orthoformate, or a method in which an alcohol directly acts in the presence of an organic amine.
- R 1 is the same or different and represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a vinyl group
- X represents a halogen atom
- m represents an integer of 0 to 2
- n represents 0 to Indicates an integer of 2.
- R 2 is the same or different and represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a vinyl group
- Y represents a halogen atom, a hydrogen atom, or an alkoxy group
- m ′ represents 0 to 2 Indicates an integer.
- the alkyl group having 1 to 4 carbon atoms represented by R 1 and R 2 may be an alkyl group represented by R 1 and R 2 in the general formula (5).
- the halogen atom represented by X and Y include, for example, a bromine atom and a chlorine atom, and the alkoxy group represented by Y is represented by the above general formula (5). Examples thereof include those exemplified as the alkoxy group represented by —OR 4 .
- alkyl group possessed by the trialkyl orthoformate examples include those exemplified as the alkyl group having 1 to 4 carbon atoms represented by R 2 or R 4 in the general formula (5).
- trimeryl orthoformate triethyl orthoformate Etc.
- a compound having two or more alkoxy groups such as acetone dimethyl acetal may be used.
- the second method is a method in which an organosilane compound represented by the following general formula (7) and an organosilane compound represented by the following general formula (8) are subjected to a coupling reaction in the presence of a metal, and then alcohol. Is a method in which a halogen atom is converted to an alkoxy group by directly acting.
- R 1 is the same or different and represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a phenyl group, X represents a halogen atom, m represents an integer of 0 to 2, and n represents 1 to Indicates an integer of 2.
- R 2 is the same or different and represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a phenyl group
- Y represents a halogen atom, a hydrogen atom, or an alkoxy group
- m ′ represents 0 to 2 Represents an integer (provided that at least one of Y and R 2 is a hydrogen atom))
- the alkyl group having 1 to 4 carbon atoms represented by R 1 and R 2 may be an alkyl group represented by R 1 and R 2 in the general formula (1).
- Examples of the alkyl group 4 include those exemplified as X and Y.
- Examples of the halogen atom represented by X and Y include a bromine atom and a chlorine atom.
- Examples of metals that can be used in the second method include platinum compounds such as hexachloroplatinic acid and rhodium compounds.
- Examples of the alcohol that can be used in the second method include those having an alkyl group having 1 to 4 carbon atoms.
- the method for producing a silicon-containing insulating film according to an embodiment of the present invention is not limited, but is preferably performed by chemical vapor deposition (CVD), particularly plasma excitation It is preferable to carry out by the CVD method (PECVD method).
- CVD chemical vapor deposition
- PECVD method the CVD method
- compound 1 at least one compound selected from compounds 2 to 4 and, if necessary, a pore-forming agent are vaporized by a vaporizer, introduced into a film forming chamber, and fed by a high frequency power source.
- a plasma CVD film can be formed on a substrate in the film formation chamber by applying plasma to the electrode in the film formation chamber to generate plasma.
- Examples of the substrate on which the silicon-containing insulating film according to the present embodiment is formed include Si-containing layers such as Si, SiO 2 , SiN, SiC, and SiCN. At this time, a gas such as argon or helium, or an oxidant such as oxygen or nitrous oxide can be introduced into the film formation chamber for the purpose of generating plasma.
- a thin film (deposited film) suitable as a low dielectric constant material for a semiconductor device can be formed by forming a film using the chemical vapor deposition material according to the present embodiment with a PECVD apparatus.
- the plasma generation method of the PECVD apparatus is not particularly limited, and for example, inductively coupled plasma, capacitively coupled plasma, ECR plasma, or the like can be used.
- the film thickness of the silicon-containing deposited film thus obtained is preferably 0.05 to 5.0 ⁇ m. Thereafter, the silicon-containing insulating film can be formed by subjecting the obtained deposited film to a curing treatment.
- the curing treatment may be at least one selected from heating, electron beam irradiation, ultraviolet irradiation, and oxygen plasma, and a plurality of treatments may be selected from these and performed simultaneously.
- a deposited film formed by chemical vapor deposition is heated to 80 ° C. to 450 ° C. under an inert atmosphere or under reduced pressure.
- a heating method at this time a hot plate, an oven, a furnace, or the like can be used, and a heating atmosphere can be performed under an inert atmosphere or under reduced pressure.
- At least one treatment selected from electron beam irradiation, ultraviolet irradiation, and oxygen plasma can be performed to improve the mechanical strength of the formed silicon-containing insulating film.
- a silicon-containing insulating film can be formed.
- the hole forming agent used in the method for producing a silicon-containing insulating film will be described.
- the pore-forming agent include a compound having a ring structure, preferably a compound having two or more rings in the molecule (polycyclic compound), more preferably a compound having a condensed ring.
- a polycyclic hydrocarbon or a monocyclic hydrocarbon and a compound containing a hetero atom (an oxygen atom, a nitrogen atom, or a fluorine atom, preferably an oxygen atom).
- the size and number of porous holes present in the insulating film are important, and factors determining the size of the porous holes One is the type of pore-forming agent used.
- the pore-forming agent is preferably a polycyclic compound, and the polycyclic compound is, for example, a 3-membered ring compound or a 4-membered ring A compound and / or a compound having a 7-membered ring structure or more, for example, an oxabicyclo compound such as cyclopentene oxide or bicycloheptadiene (BCHD).
- the polycyclic compound is, for example, a 3-membered ring compound or a 4-membered ring A compound and / or a compound having a 7-membered ring structure or more, for example, an oxabicyclo compound such as cyclopentene oxide or bicycloheptadiene (BCHD).
- the chemical vapor deposition material (composition) according to the present embodiment contains a pore forming agent, it contains 0.05 to 10,000 parts by weight of the pore forming agent with respect to 100 parts by weight of the total organosilane compound. It is more preferable that it contains 0.1 to 5000 parts by weight of a pore forming agent.
- the content of the pore forming agent is less than 0.05 with respect to 100 parts by weight of the total organosilane compound, the relative dielectric constant is reduced. On the other hand, if it exceeds 10,000 parts by weight, a uniform film may not be obtained.
- Oxabicyclo Compound examples include 6-oxabicyclo [3.1.0] hexane (cyclopentene oxide), 7-oxabicyclo [4.1.0] heptane (cyclohexene oxide), 9-oxabicyclo [ 6.1.0] nonane (cyclooctene oxide), 7-oxabicyclo [2.2.1] heptane (1,4-epoxycyclohexane).
- examples of the oxabicyclo compound include 9-oxabicyclo [6.1.0] non-4-ene compound.
- the oxabicyclo compound is not limited, for example, 7-oxabicyclo [4.1.0] heptan-2-one, 3-oxabicyclo [3.1.0] hexane-2,4-dione, and the like. May be a compound having an additional functional group such as ketone, aldehyde, amine, amide, imide, ether, ester, anhydride, carbonate, thiol, or thioether.
- polycyclic hydrocarbon preferably has 6 to 12 carbon atoms.
- 2,5-norbomadiene bicyclo [2.2.1] hepta-2,5-diene
- norbomylene 2,5-norbornadiene bicyclo [2.2.1] hepta-2,5-diene
- norbornane bicyclo [2.2.1] heptane
- tricyclo [3.2.1.0] octane tricyclo Examples include [3.2.2.0] nonane, spiro [3.4] octane, spiro [4.5] nonane, and spiro [5.6] decane.
- Monocyclic hydrocarbons examples include alicyclic hydrocarbons having 5 to 12 carbon atoms such as cyclopentane and cyclohexane, benzene, toluene, xylene (o-xylene, m-xylene, n An aromatic hydrocarbon having 6 to 12 carbon atoms, such as -xylene).
- Silicon-containing insulating film A silicon-containing insulating film according to an embodiment of the present invention can be obtained by the above-described manufacturing method.
- the silicon-containing insulating film according to this embodiment has a low dielectric constant and excellent surface flatness, it is particularly excellent as an interlayer insulating film for semiconductor elements such as LSI, system LSI, DRAM, SDRAM, RDRAM, and D-RDRAM.
- protective films such as etching stopper films, surface coating films of semiconductor elements, intermediate layers of semiconductor manufacturing processes using multilayer resists, interlayer insulating films of multilayer wiring boards, protective films and insulating films for liquid crystal display elements, etc. It can be used suitably.
- the silicon-containing insulating film according to the present embodiment is suitable for a semiconductor device formed by, for example, a copper damascene process.
- the silicon-containing insulating film according to the present embodiment is formed using the above-described chemical vapor deposition material, a —Si— (CH 2 ) n —Si—O— moiety (where n is an integer of 1 to 3) Can be included). Since the silicon-containing insulating film according to the present embodiment has the above-described site, it has excellent drug resistance and can suppress an increase in relative dielectric constant during processing, so that it has a low relative dielectric constant and excellent processing resistance. Yes.
- the relative dielectric constant of the silicon-containing insulating film according to this embodiment is preferably 3.0 or less, more preferably 1.8 to 3.0, and still more preferably 2.2 to 3.0.
- the elastic modulus of the silicon-containing insulating film according to this embodiment is preferably 4.0 to 18.0 GPa, more preferably 4.0 to 15.0 GPa, and further preferably 10.0 to 12.0 GPa.
- the hardness is preferably 0.1 GPa or more, and more preferably 1.0 GPa or more. From these, it can be said that the silicon-containing insulating film according to this embodiment is extremely excellent in insulating film characteristics such as mechanical strength and relative dielectric constant.
- a silicon-containing insulating film was formed on an 8-inch silicon wafer by PECVD under the conditions described later.
- An aluminum electrode pattern was formed on the obtained film by a vapor deposition method, and a sample for measuring relative permittivity was prepared.
- the relative dielectric constant of the insulating film was measured at a frequency of 100 kHz by the CV method using an HP16451B electrode and an HP4284A precision LCR meter manufactured by Yokogawa Hewlett-Packard Co., Ltd.
- ⁇ k is the difference between the relative dielectric constant (k @ RT) measured in an atmosphere of 24 ° C.
- Remaining film ratio (%) (film thickness after immersion) / (film thickness before immersion) ⁇ 100 A: The remaining film rate is 99% or more.
- the remaining film rate is 90% or more and less than 99%.
- the remaining film rate is 70% or more and less than 90%.
- Remaining film rate is less than 70%.
- Plasma Ashing Resistance Evaluation An 8-inch wafer on which a silicon-containing insulating film is formed is exposed to organic photoresist ashing conditions using nitrogen and hydrogen using a plasma ashing apparatus manufactured by Tokyo Electron, and the dielectric constant before and after the exposure of the insulating film. Plasma ashing resistance was evaluated from the change. The following evaluation was made according to the change in the dielectric constant before and after the exposure.
- the residual water content is 117 ppm
- K 1.2 ppb
- Fe 1.3 ppb
- Each element of Li, Mg, Cr, Ag, Cu, Zn, Mn, Co, Ni, Ti, Zr, Al, Pb, Sn, and W was below the detection limit value (0.2 ppb). From the above results, it was confirmed that the organosilane compound obtained in this synthesis example had sufficient purity as an insulating film forming material.
- the residual water content is 131 ppm
- K 1.1 ppb
- Fe 1.5 ppb
- Each element of Li, Mg, Cr, Ag, Cu, Zn, Mn, Co, Ni, Ti, Zr, Al, Pb, Sn, and W was below the detection limit value (0.2 ppb). From the above results, it was confirmed that the organosilane compound obtained in this synthesis example had sufficient purity as an insulating film forming material.
- the residual water content is 176 ppm
- K 1.6 ppb
- Fe 1.9 ppb
- Each element of Li, Mg, Cr, Ag, Cu, Zn, Mn, Co, Ni, Ti, Zr, Al, Pb, Sn, and W was below the detection limit value (0.2 ppb). From the above results, it was confirmed that the organosilane compound obtained in this synthesis example had sufficient purity as an insulating film forming material.
- the residual moisture content is 129 ppm
- K 1.3 ppb
- Fe 1.1 ppb
- Each element of Li, Mg, Cr, Ag, Cu, Zn, Mn, Co, Ni, Ti, Zr, Al, Pb, Sn, and W was below the detection limit value (0.2 ppb). From the above results, it was confirmed that the organosilane compound obtained in this synthesis example had sufficient purity as an insulating film forming material.
- the residual moisture content is 127 ppm
- K 1.0 ppb
- Fe 1.3 ppb
- Each element of Li, Mg, Cr, Ag, Cu, Zn, Mn, Co, Ni, Ti, Zr, Al, Pb, Sn, and W was below the detection limit value (0.2 ppb). From the above results, it was confirmed that the organosilane compound obtained in this synthesis example had sufficient purity as an insulating film forming material.
- the residual water content is 107 ppm
- K 1.1 ppb
- Fe 1.7 ppb
- Each element of Li, Mg, Cr, Ag, Cu, Zn, Mn, Co, Ni, Ti, Zr, Al, Pb, Sn, and W was below the detection limit value (0.2 ppb). From the above results, it was confirmed that the organosilane compound obtained in this synthesis example had sufficient purity as an insulating film forming material.
- the residual water content is 162 ppm
- K 1.1 ppb
- Fe 1.0 ppb
- Each element of Li, Mg, Cr, Ag, Cu, Zn, Mn, Co, Ni, Ti, Zr, Al, Pb, Sn, and W was below the detection limit value (0.2 ppb). From the above results, it was confirmed that the organosilane compound obtained in this synthesis example had sufficient purity as an insulating film forming material.
- the residual moisture content is 112 ppm
- K 1.9 ppb
- Fe 2.0 ppb
- Each element of Li, Mg, Cr, Ag, Cu, Zn, Mn, Co, Ni, Ti, Zr, Al, Pb, Sn, and W was below the detection limit value (0.2 ppb). From the above results, it was confirmed that the organosilane compound obtained in this synthesis example had sufficient purity as an insulating film forming material.
- the residual moisture content is 41 ppm
- K 1.5 ppb
- Fe 1.8 ppb
- Each element of Li, Mg, Cr, Ag, Cu, Zn, Mn, Co, Ni, Ti, Zr, Al, Pb, Sn, W, and Pt was below the detection limit value (0.2 ppb). From the above results, it was confirmed that the organosilane compound obtained in this synthesis example had sufficient purity as an insulating film forming material.
- the purity obtained by the GC method was 99.0%.
- the residual moisture content is 185 ppm
- K 1.1 ppb
- Fe 1.7 ppb
- Each element of Li, Mg, Cr, Ag, Cu, Zn, Mn, Co, Ni, Ti, Zr, Al, Pb, Sn, W, and Pt was below the detection limit value (0.2 ppb). From the above results, it was confirmed that the organosilane compound obtained in this synthesis example had sufficient purity as an insulating film forming material.
- the residual moisture content is 45 ppm
- K 1.1 ppb
- Fe 1.3 ppb
- Each element of Li, Mg, Cr, Ag, Cu, Zn, Mn, Co, Ni, Ti, Zr, Al, Pb, Sn, W, and Pt was below the detection limit value (0.2 ppb). From the above results, it was confirmed that the organosilane compound obtained in this synthesis example had sufficient purity as an insulating film forming material.
- the residual moisture content is 185 ppm
- K 1.1 ppb
- Fe 1.7 ppb
- Each element of Li, Mg, Cr, Ag, Cu, Zn, Mn, Co, Ni, Ti, Zr, Al, Pb, Sn, W, and Pt was below the detection limit value (0.2 ppb). From the above results, it was confirmed that the organosilane compound obtained in this synthesis example had sufficient purity as an insulating film forming material.
- Reference synthesis example 1 A three-necked flask equipped with a cooling condenser and a dropping funnel was dried at 50 ° C. under reduced pressure, and then charged with nitrogen. Next, 20 g of magnesium and 500 ml of THF were added to the flask, and 25 g of (chloromethyl) trimethylsilane was added with stirring at room temperature. After stirring for a while and confirming heat generation, 55 g of (chloromethyl) trimethylsilane was added from a dropping funnel over 30 minutes.
- the residual moisture content is 120 ppm
- K 1.5 ppb
- Fe 1.1 ppb
- Each element of Li, Mg, Cr, Ag, Cu, Zn, Mn, Co, Ni, Ti, Zr, Al, Pb, Sn, W, and Pt was below the detection limit value (0.2 ppb). From the above results, it was confirmed that the organosilane compound obtained in this synthesis example had sufficient purity as an insulating film forming material.
- Reference synthesis example 2 A three-necked flask equipped with a cooling condenser and a dropping funnel was dried at 50 ° C. under reduced pressure, and then charged with nitrogen. Next, 20 g of magnesium and 500 ml of THF were added to the flask, and 25 g of (chloromethyl) methyldivinylsilane was added with stirring at room temperature. After stirring for a while and confirming heat generation, 48 g of (chloromethyl) methyldivinylsilane was added from a dropping funnel over 30 minutes.
- the residual moisture content is 116 ppm
- K 2.1 ppb
- Fe 2.0 ppb
- Each element of Li, Mg, Cr, Ag, Cu, Zn, Mn, Co, Ni, Ti, Zr, Al, Pb, Sn, W, and Pt was below the detection limit value (0.2 ppb). From the above results, it was confirmed that the organosilane compound obtained in this synthesis example had sufficient purity as an insulating film forming material.
- Reference synthesis example 3 A three-necked flask equipped with a cooling condenser and a dropping funnel was dried at 50 ° C. under reduced pressure, and then charged with nitrogen. Next, 500 ml of THF and 353 g of 1,2-bis (triethoxysilyl) vinylene were added to the flask, and 2 L of a 1 mol / L THF solution of ethylmagnesium bromide was added with stirring at room temperature. After reacting at 60 ° C.
- Reference synthesis example 4 A three-necked flask equipped with a cooling condenser and a dropping funnel was dried at 50 ° C. under reduced pressure, and then charged with nitrogen. Next, 500 ml of toluene was added to the flask, and 129 g of ethyldichlorosilane and 142 g of vinyltriethylsilane were added while stirring at room temperature. The mixture was stirred for a while, and 100 mg of chloroplatinic acid was added thereto and reacted at 100 degrees for 5 hours. After cooling this to room temperature, 160 g of pyridine was added dropwise while adding 160 g of pyridine and stirring.
- the residual moisture content is 95 ppm
- K 1.1 ppb
- Fe 1.8 ppb
- Each element of Li, Mg, Cr, Ag, Cu, Zn, Mn, Co, Ni, Ti, Zr, Al, Pb, Sn, W, and Pt was below the detection limit value (0.2 ppb). From the above results, it was confirmed that the organosilane compound obtained in this synthesis example had sufficient purity as an insulating film forming material.
- Example 2 A silicon-containing film 0.5 ⁇ m was formed on a silicon substrate under the same conditions as in Example 1 except that the same apparatus as in Example 1 was used and that the bis (dimethoxymethylsilyl) methane synthesized in Synthesis Example 1 was used as the silica source. A film was formed.
- Example 3 Using the same apparatus as in Example 1, the 1,1,3,3-tetramethoxy-1,3-disilabutane synthesized in Synthesis Example 2 was used as a silica source, and O 2 gas was supplied at a gas flow rate of 1.0 sccm. A silicon-containing film having a thickness of 0.5 ⁇ m was formed on a silicon substrate under the same conditions as in Example 1 except that the silicon-containing film was supplied.
- Example 4 The same apparatus as in Example 1 was used, except that bis (dimethoxysilyl) methane synthesized in Synthesis Example 3 was used as a silica source, and that O 2 gas was supplied at a gas flow rate of 1.0 sccm. Under the same conditions, a silicon-containing film of 0.5 ⁇ m was formed on the silicon substrate.
- Table 1 shows the evaluation results of the silicon-containing films obtained in Examples 1 to 6 and Comparative Examples 1 to 3, respectively.
- Example 5 Using a two-frequency plasma CVD apparatus manufactured by Utec, using 1,1,1,3,3-pentamethoxy-1,3-disilabutane (gas flow rate: 0.3 sccm) synthesized in Synthesis Example 4 as a silica source, Bicyclo- [2.2.1] -hepta-2,5-diene (gas flow rate: 0.6 sccm) was used as the pore forming agent, Ar gas flow rate was 100 sccm, and RF upper shower head power was 300 W (27.12 MHz). ), A lower substrate power of 150 W (380 kHz), a substrate temperature of 300 ° C., and a reaction pressure of 10 Torr, a silicon-containing insulating film of 0.5 ⁇ m was formed on the silicon substrate.
- Bicyclo- [2.2.1] -hepta-2,5-diene gas flow rate: 0.6 sccm
- Ar gas flow rate was 100 sccm
- RF upper shower head power was
- Example 6 Using a 2-frequency plasma CVD apparatus manufactured by U-Tech, using 2,2,4-trimethoxy-4-methyl-2,4-disilapentane obtained in Synthesis Example 5 as a silica source, the gas flow rate was 0.3 sccm, and Bicyclo- [2.2.1] -hepta-2,5-diene was used as the pore forming agent, and the gas flow rate was 0.6 sccm, Ar gas flow rate 100 sccm, RF upper shower head power 300 W (27.12 MHz), lower part A silicon-containing insulating film of 0.5 ⁇ m was formed on a silicon substrate at a substrate power of 150 W (380 kHz), a substrate temperature of 300 ° C., and a reaction pressure of 10 Torr.
- a 2-frequency plasma CVD apparatus manufactured by U-Tech, using 2,2,4-trimethoxy-4-methyl-2,4-disilapentane obtained in Synthesis Example 5 as a silica source, the gas flow rate was
- Comparative Example 1 A silicon-containing insulating film of 0.5 ⁇ m was formed on a silicon substrate under the same conditions as in Example 6 except that methyltrimethoxysilane was used as the silica source using the same apparatus as in Example 6.
- Example 7 Using the same apparatus as in Example 1, bis (dimethoxyvinylsilyl) methane (gas flow rate: 0.3 sccm) synthesized in Synthesis Example 6 was used as the silica source, and cyclopentene oxide (gas flow rate: 0. A silicon-containing film of 0.5 ⁇ m was formed on the silicon substrate under the same conditions as in Example 1 except that 6 sccm) was used.
- Example 8 Using the same apparatus as in Example 5, 1,1,1,3,3-pentamethoxy-3-vinyl-1,3-disilapropane synthesized in Synthesis Example 7 as a silica source and cyclopentene oxide as a pore forming agent were used. A silicon-containing film of 0.5 ⁇ m was formed on the silicon substrate under the same conditions as in Example 5 except that these gas flow rates were set to 0.6 sccm.
- Example 9 Using the same apparatus as in Example 6, 1,1,1,3-tetramethoxy-3,3-divinyl-1,3-disilapropane obtained in Synthesis Example 8 as a silica source, and cyclopentene as a pore-forming agent A silicon-containing insulating film of 0.5 ⁇ m was formed on the silicon substrate under the same conditions as in Example 6 except that the gas flow rate was changed to 0.6 sccm using oxide.
- Comparative Example 3 A silicon-containing insulating film of 0.5 ⁇ m was formed on a silicon substrate under the same conditions as in Example 11 except that vinyltrimethoxysilane was used as a silica source using the same apparatus as in Example 9.
- Example 10 Using the same apparatus as in Example 1, 1,2-bis (diethoxyethylsilyl) ethane (gas flow rate: 0.3 sccm) synthesized in Synthesis Example 9 was used as the silica source, and p-xylene was used as the pore forming agent. A silicon-containing film of 0.5 ⁇ m was formed on the silicon substrate under the same conditions as in Example 1 except that (gas flow rate: 0.6 sccm) was used.
- Example 11 Using the same apparatus as in Example 5, 1,1,1,4,4-pentaethoxy-1,4-disilahexane synthesized in Synthesis Example 10 as a silica source, and cyclopentene oxide as a pore-forming agent, these A silicon-containing film of 0.5 ⁇ m was formed on the silicon substrate under the same conditions as in Example 5 except that the gas flow rate was 0.6 sccm.
- Example 12 Using the same apparatus as in Example 6, 3,3,6-triethoxy-6-ethyl-3,6-disilaoctane obtained in Synthesis Example 11 was used as the silica source, and p-xylene was used as the pore forming agent. A silicon-containing insulating film of 0.5 ⁇ m was formed on the silicon substrate under the same conditions as in Example 6 except that the gas flow rate was 0.6 sccm.
- Example 13 Using the same apparatus as in Example 6, 1,1,1,4-tetraethoxy-1,4-disilahexane synthesized in Synthesis Example 12 was used as the silica source, and p-xylene was used as the pore forming agent. A silicon-containing film 0.5 ⁇ m was formed on the silicon substrate under the same conditions as in Example 6 except that the gas flow rate was 0.6 sccm and that O 2 gas was supplied at a gas flow rate of 1.0 sccm. .
- Comparative Example 5 On the silicon substrate under the same conditions as in Example 10 except that 1,2-bis (diethoxyethylsilyl) vinylene synthesized in Reference Synthesis Example 3 was used as a silica source using the same apparatus as in Example 10. A silicon-containing film of 0.5 ⁇ m was formed.
- Example 14 The same apparatus as in Example 1 was used, except that bis (dimethoxymethylsilyl) methane (gas flow rate: 0.06 sccm) and diethoxymethylsilane (gas flow rate: 0.24 sccm) synthesized in Synthesis Example 1 were used as silica sources. In the same conditions as in Example 1, a 0.5 ⁇ m silicon-containing film was formed on a silicon substrate.
- Example 15 The same apparatus as in Example 1 was used, except that bis (dimethoxymethylsilyl) methane (gas flow rate: 0.24 sccm) and diethoxymethylsilane (gas flow rate: 0.06 sccm) synthesized in Synthesis Example 1 were used as silica sources. In the same conditions as in Example 1, a 0.5 ⁇ m silicon-containing film was formed on a silicon substrate.
- Example 16 Bis (dimethoxymethylsilyl) methane and diethoxymethylsilane synthesized in Synthesis Example 1 are mixed at a molar ratio of 20:80, and bis (dimethoxymethylsilyl) methane and diethoxymethylsilane and a pore-forming agent are mixed together.
- the materials for chemical vapor deposition were prepared by mixing at a weight ratio of 1: 1.
- a silicon-containing film of 0.5 ⁇ m is formed on a silicon substrate under the same conditions as in Example 1, except that the same apparatus as in Example 1 is used and the prepared chemical vapor deposition material is used as the silica source. did.
- Example 17 Bis (dimethoxymethylsilyl) methane synthesized in Synthesis Example 1 and diethoxymethylsilane are mixed at a molar ratio of 80:20, and bis (dimethoxymethylsilyl) methane, diethoxymethylsilane and a pore-forming agent are mixed together.
- the materials for chemical vapor deposition were prepared by mixing at a weight ratio of 1: 1.
- a silicon-containing film of 0.5 ⁇ m is formed on a silicon substrate under the same conditions as in Example 1, except that the same apparatus as in Example 1 is used and the prepared chemical vapor deposition material is used as the silica source. did.
- Example 18 A material for chemical vapor deposition by mixing bis (dimethoxymethylsilyl) methane synthesized in Synthesis Example 1 and bicyclo- (2.2.1) -hepta-2,5-diene at a weight ratio of 1: 1. Was prepared.
- Example 2 Using the same apparatus as in Example 1, using a material for chemical vapor deposition (gas flow rate: 0.3 sccm) prepared as a silica source, Ar gas flow rate 100 sccm, RF upper shower head power 300 W (27.12 MHz) A silicon-containing insulating film of 0.5 ⁇ m was formed on the silicon substrate at a lower substrate power of 150 W (380 kHz), a substrate temperature of 300 ° C., and a reaction pressure of 10 Torr.
- gas flow rate gas flow rate: 0.3 sccm
- Ar gas flow rate 100 sccm Ar gas flow rate 100 sccm
- RF upper shower head power 300 W 27.12 MHz
- a silicon-containing insulating film of 0.5 ⁇ m was formed on the silicon substrate at a lower substrate power of 150 W (380 kHz), a substrate temperature of 300 ° C., and a reaction pressure of 10 Torr.
- Evaluation Results Table 1 shows the evaluation results of the silicon-containing insulating films obtained in Examples 1 to 18 and Comparative Examples 1 to 6.
- the silicon-containing films obtained in Examples 1 to 18 were very excellent in mechanical strength, had low ⁇ k, which is an index indicating the relative dielectric constant and hygroscopicity, and were also excellent in chemical resistance and ashing resistance. .
- the ashing resistance of the silicon-containing films of Examples 1 to 9 was further superior to the ashing resistance of the silicon-containing films of Examples 10 to 13. This is because ashing resistance in the formed film is higher when the skeleton structure of the raw silicon compound used for film formation is Si—CH 2 —Si than when Si—CH 2 —CH 2 —Si is used. Means excellent.
- the carbon chain connecting two silicon atoms is a methylene chain
- each silicon atom is a monovalent hydrocarbon group (for example, an alkyl group having 1 to 4 carbon atoms, a vinyl group, or a phenyl group).
- the films of Examples 2, 3 and 7 formed using the substituted organosilicon compound were extremely excellent in chemical resistance and ashing resistance.
- the film obtained in Comparative Example 1 has substantially the same relative dielectric constant and ⁇ k as the films obtained in Examples 1 to 6, but the mechanical strength, chemical resistance, and ashing are similar. Resistance was inferior.
- the film obtained in Comparative Example 2 was slightly lower in mechanical strength than the films obtained in Examples 1 to 6, although the relative dielectric constant, ⁇ k, and chemical resistance and ashing resistance were almost the same. It was.
- the film obtained in Comparative Example 3 was inferior in mechanical strength, chemical resistance and ashing resistance to the film obtained in Example 7, although the relative dielectric constant and ⁇ k were almost the same.
- the film obtained in Comparative Example 4 was slightly lower in mechanical strength than the films obtained in Examples 7 to 9, although the relative dielectric constant, ⁇ k, and chemical solution resistance and ashing resistance were almost equivalent. .
- Comparative Example 5 a film was formed using an organosilane compound in which the ethylene chain in the organosilane compound used in Example 10 was replaced with a vinylene chain.
- the film of Comparative Example 5 has a relative permittivity, ⁇ k, and mechanical strength almost the same as those of Examples 10-13, but has lower chemical resistance and ashing resistance than the films of Examples 10-13. I understood.
- the film obtained in Comparative Example 6 was slightly lower in mechanical strength than the films obtained in Examples 10 to 13, although the relative dielectric constant, ⁇ k, and chemical resistance and ashing resistance were almost equivalent. .
- the silicon-containing film according to the present invention has excellent mechanical strength, low dielectric constant, and further excellent processing resistance such as moisture absorption resistance, chemical resistance and ashing resistance, and storage stability. It can be suitably used as an interlayer insulating film for semiconductor elements and the like.
- the present invention includes configurations that are substantially the same as the configurations described in the embodiments (for example, configurations that have the same functions, methods, and results, or configurations that have the same purposes and results).
- the invention includes a configuration in which a non-essential part of the configuration described in the embodiment is replaced.
- the present invention includes a configuration that achieves the same effect as the configuration described in the embodiment or a configuration that can achieve the same object.
- the invention includes a configuration in which a known technique is added to the configuration described in the embodiment.
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Abstract
Description
(式中、R1およびR2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、またはフェニル基を示し、R3およびR4は同一または異なり、炭素数1~4のアルキル基、アセチル基、またはフェニル基を示し、mおよびm’は同一または異なり、nは1~3の整数を示す。)
上記化学気相成長法用材料を化学気相成長法により基板に堆積させて堆積膜を形成する工程と、
前記堆積膜について、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種の硬化処理を行う工程と、
を含む。
1.1.化学気相成長法用材料(第1実施形態)
本発明の一実施形態に係る化学気相成長法用材料は、下記一般式(1)で示される有機シラン化合物(以下、「化合物1」ともいう。)を含む。
ケース(i)の有機シラン化合物の場合、上記一般式(1)で表される有機シラン化合物は、双方のケイ素原子の置換度が対称である。すなわち、上記一般式(1)で表される有機シラン化合物は、双方のケイ素原子が同じ数のOR基(ここで、Rは水素原子、炭素数1~4のアルキル基、ビニル基、またはフェニル基を示す。)によって置換されている。これにより、ケース(i)の有機シラン化合物を用いることにより、加工耐性と機械的強度とのバランスが膜全体で均一である膜を得ることができる。
ケース(ii)の有機シラン化合物を用いて得られた絶縁膜は、機械的強度が非常に優れており、かつ、低誘電率で加工耐性が高い。この場合、詳細な機構は明らかではないが、上記一般式(1)で表される有機シラン化合物のうち-Si-(OR3)3部分および-Si-(OR4)2部分が-Si-O-Si-結合を形成し、3次元の架橋度の高い骨格を形成し、この骨格が機械的強度の大きさに寄与し、かつ、-Si-(CH2)n-Si-R2部分がRIEから受けるダメージを弱め、またフッ素酸系の薬液に対する耐性を高めると推測される。
ケース(iii)の有機シラン化合物の場合、上記一般式(1)で表される有機シラン化合物は、一方のケイ素原子の2つの置換基のみ、あるいは一方のケイ素原子の2つの置換基と他方のケイ素原子の1つの置換基が水素原子、炭素数1~4のアルキル基、ビニル基、フェニル基のいずれかで置換されており、酸素原子は一方のケイ素原子の一つの置換基と他方のケイ素原子の2つまたは3つの置換基と結合している。
、ケイ素、炭素、酸素、および水素以外の元素(以下、「不純物」ともいう。)の含有量が10ppb未満であり、かつ含水分量が0.1%未満であることが好ましい。このような絶縁膜形成用材料を用いて絶縁膜を形成することにより、低比誘電率でかつ加工耐性に優れた絶縁膜を収率良く得ることができる。
本発明の一実施形態に係る化学気相成長法用材料は、下記一般式(2)で表されるシラン化合物(以下、「化合物2」ともいう。)、下記一般式(3)で表されるシラン化合物(以下、「化合物3」ともいう。)、および下記一般式(4)で表されるシラン化合物(以下、「化合物4」ともいう。)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。)を含むことができる。化合物2~4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。また、本発明の一実施形態に係る化学気相成長法用材料は、(II)成分とともに、後述する空孔形成剤をさらに含むことができる。
(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0~4の整数を示す。)
R8 b(R9O)3-bSi-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、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の整数を示し、gは0または1を示し、hは2~30の数を示す。)
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。
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。
本実施の形態に係る化合物4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。
上記一般式(1)で表される有機シラン化合物の製造方法としては、特に限定されるものではないが、例えば、下記の第1および第2の方法が挙げられる。
第1の方法は、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た後、ハロゲン化水素を反応させてフェニル基をハロゲン原子に置換し、その後、オルトギ酸トリアルキルを用いて当該ハロゲン原子をアルコキシ基に置換する方法または有機アミン存在下アルコールを直接作用させる方法である。
(式中、R1は同一または異なり、水素原子、炭素数1~4のアルキル基、またはビニル基を示し、Xはハロゲン原子を示し、mは0~2の整数を示し、nは0~2の整数を示す。)
(式中、R2は同一または異なり、水素原子、炭素数1~4のアルキル基、またはビニル基を示し、Yはハロゲン原子、水素原子、またはアルコキシ基を示し、m’は0~2の整数を示す。)
第2の方法は、下記一般式(7)で表される有機シラン化合物と下記一般式(8)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た後、アルコールを直接作用させてハロゲン原子をアルコキシ基に変換する方法である。
(式中、R1は同一または異なり、水素原子、炭素数1~4のアルキル基、またはフェニル基を示し、Xはハロゲン原子を示し、mは0~2の整数を示し、nは1~2の整数を示す。)
(式中、R2は同一または異なり、水素原子、炭素数1~4のアルキル基、またはフェニル基を示し、Yはハロゲン原子、水素原子、またはアルコキシ基を示し、m’は0~2の整数を示す(ただし、YおよびR2のうち少なくとも1つは水素原子である。))
本発明の一実施形態に係るケイ素含有絶縁膜の製造方法は、限定されるものではないが、化学気相成長法(CVD法)による行うことが好ましく、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、化合物1と、必要に応じて化合物2~4から選ばれる少なくとも1種の化合物と空孔形成剤と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。
次に、ケイ素含有絶縁膜の製造方法において用いられる空孔形成剤について説明する。空孔形成剤としては、例えば、環構造を有する化合物が挙げられ、好ましくは、分子中に2以上の環を有する化合物(多環性化合物)であり、より好ましくは縮合環を有する化合物であり、例えば、多環性炭化水素または単環性炭化水素や、ヘテロ原子(酸素原子、窒素原子、またはフッ素原子、好ましくは酸素原子)を含む化合物が挙げられる。
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は上記製造方法により得ることができる。
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。
精製した有機シラン化合物中の水分量および不純物含有量は、カールフィッシャー水分計(平沼産業社製、微量水分測定装置AQ-7)および原子吸光分光光度計(日立ハイテク社製、偏光ゼーマン原子吸光分光光度計Z-5700)を用いて測定した。
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、吸水性の高い有機シリカ膜であるといえる。
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、0.2%の希フッ酸水溶液中に室温で3分間浸漬し、浸漬前後のケイ素含有絶縁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。
ケイ素含有絶縁膜が形成された8インチウエハを、東京エレクトロン社製プラズマアッシング装置を用いて、窒素および水素を用いる有機フォトレジストアッシング条件に暴露し、絶縁膜の暴露前後の誘電率変化よりプラズマアッシング耐性を評価した。暴露前後の誘電率変化に応じて次のように評価した。
A 比誘電率の上昇値が0.1以上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
5.2.1.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30gおよびTHF500mlを加え、室温で撹拌しながら(クロロメチル)メチルジフェニルシラン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)メチルジフェニルシラン222gを1時間かけて加えた。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およびメチルジフェニルクロロシラン233g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、3%塩化アンモニウム水溶液を加え反応を失活させ、ジエチルエーテル500mlを添加した後、有機相を3%塩化ナトリウム水溶液1Lで2回洗浄した。この有機相を硫酸マグネシウムを用いて乾燥させた後減圧濃縮して得られた粗生成物をシリカゲルクロマトグラフィーで分離することにより、ビス(ジフェニルメチルシリル)メタン334g(収率82%)を得た。
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30gおよびTHF500mlを加え、室温で撹拌しながら(クロロメチル)メチルジフェニルシラン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)メチルジフェニルシラン222gを1時間かけて加えた。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およびジフェニルクロロシラン219g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、3%塩化アンモニウム水溶液を加え反応を失活させ、ジエチルエーテル500mlを添加した後、有機相を3%塩化ナトリウム水溶液1Lで2回洗浄した。この有機相を硫酸マグネシウムを用いて乾燥させた後減圧濃縮して得られた粗生成物をシリカゲルクロマトグラフィーで分離することにより、1,1,3,3-テトラフェニル-1,3-ジシラブタン324g(収率82%)を得た。
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、フラスコ内にビス(ジクロロシリル)メタン214gおよびTHF500mlを加え、室温で撹拌しながら、次いで滴下ロートからオルトギ酸トリメチル424gを2時間かけて室温で滴下した。滴下後、室温で2日撹拌し、反応液を蒸留で分離することで、ビス(ジメトキシシリル)メタンを169g(収率85%)得た。この化合物のGC法で得られた純度は99.1%であった。また、残存水分量は176ppm、ケイ素、炭素、酸素、および水素以外の元素の含有量(金属不純物含有量)は、Na=1.2ppb、K=1.6ppb、Fe=1.9ppbであり、Li、Mg、Cr、Ag、Cu、Zn、Mn、Co、Ni、Ti、Zr、Al、Pb、Sn、Wの各元素は検出限界値(0.2ppb)以下であった。以上の結果より、本合成例で得られた有機シラン化合物は、絶縁膜形成材料としての十分な純度を備えていることが確認された。
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30gおよびTHF500mlを加え、室温で撹拌しながら(クロロメチル)メチルジフェニルシラン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)メチルジフェニルシラン222gを1時間かけて加えた。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およびトリフェニルクロロシラン320g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、3%塩化アンモニウム水溶液を加え反応を失活させ、ジエチルエーテル500mlを添加後、有機相を3%塩化ナトリウム水溶液1Lで2回洗浄した。この有機相を硫酸マグネシウムで乾燥後減圧濃縮し、この粗生成物をシリカゲルクロマトグラフィーで分離することにより、1,1,1,3,3-ペンタフェニル-1,3-ジシラブタンを410g(収率87%)得た。
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30gおよびTHF500mlを加え、室温で撹拌しながら(クロロメチル)ジメチルフェニルシラン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)ジメチルフェニルメチルシラン160gを1時間かけて加えた。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およびメチルジフェニルクロロシラン233g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、3%塩化アンモニウム水溶液を加え反応を失活させ、ジエチルエーテル500mlを添加後、有機相を3%塩化ナトリウム水溶液1Lで2回洗浄した。この有機相を硫酸マグネシウムで乾燥後減圧濃縮し、この粗生成物をシリカゲルクロマトグラフィーで分離することにより、2-メチル-2,4,4-トリフェニル-2,4-ジシラペンタンを304g(収率88%)で得た。
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30gおよびTHF500mlを加え、室温で撹拌しながら(クロロメチル)ジフェニルビニルシラン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)ジフェニルビニルシラン234gを1時間かけて加えた。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およびジフェニルビニルクロロシラン250g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、3%塩化アンモニウム水溶液を加え反応を失活させ、ジエチルエーテル500mlを添加した後、有機相を3%塩化ナトリウム水溶液1Lで2回洗浄した。この有機相を硫酸マグネシウムを用いて乾燥させた後、該有機相を減圧濃縮して得られた粗生成物をシリカゲルクロマトグラフィーで分離することにより、ビス(ジフェニルビニルシリル)メタン281g(収率65%)を得た。
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30gおよびTHF500mlを加え、室温で撹拌しながら(クロロメチル)ビニルジフェニルシラン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)ビニルジフェニルシラン234gを1時間かけて加えた。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およびトリフェニルクロロシラン320g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、3%塩化アンモニウム水溶液を加え反応を失活させ、ジエチルエーテル500mlを添加した後、有機相を3%塩化ナトリウム水溶液1Lで2回洗浄した。この有機相を硫酸マグネシウムで乾燥後、減圧濃縮し、この粗生成物をシリカゲルクロマトグラフィーで分離することにより、1,1,1,3,3-ペンタフェニル-3-ビニル-1,3-ジシラプロパンを367g(収率76%)得た。
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30gおよびTHF500mlを加え、室温で撹拌しながら(クロロメチル)ジビニルフェニルシラン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)ジビニルフェニルメチルシラン184gを1時間かけて加えた。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およびトリフェニルクロロシラン320g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、3%塩化アンモニウム水溶液を加え反応を失活させ、ジエチルエーテル500mlを添加後、有機相を3%塩化ナトリウム水溶液1Lで2回洗浄した。この有機相を硫酸マグネシウムで乾燥後減圧濃縮し、この粗生成物をシリカゲルクロマトグラフィーで分離することにより、1,1,1,3-テトラフェニル-3,3-ジビニル-1,3-ジシラプロパンを260g(収率60%)で得た。
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、フラスコ内にトルエン500mlを加え、室温で撹拌しながらエチルジクロロシラン129gおよびビニルエチルジクロロシラン155gを加えた。しばらく撹拌し、ここにクロロ白金酸100mgを加え、100℃で5時間反応させた。これを室温まで冷却させたのち、ピリジン238gを加え撹拌しながら、エタノール140gを滴下して加えた。滴下後室温で3時間反応させた後、生成した塩を濾別し、濾液を分留することで、1,2-ビス(ジエトキシエチルシリル)エタン232g(収率72%)を得た。GC法で得られた純度は99.4%であった。また、残存水分量は41ppm、ケイ素、炭素、酸素、および水素以外の元素の含有量(金属不純物含有量)は、Na=1.1ppb、K=1.5ppb、Fe=1.8ppbであり、Li、Mg、Cr、Ag、Cu、Zn、Mn、Co、Ni、Ti、Zr、Al、Pb、Sn、W、Ptの各元素は検出限界値(0.2ppb)以下であった。以上の結果より、本合成例で得られた有機シラン化合物は、絶縁膜形成用材料としての十分な純度を備えていることが確認された。
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、フラスコ内にトルエン500mlを加え、室温で撹拌しながらトリクロロシラン135gおよびエチルビニルジエトキシシラン174gを加えた。しばらく撹拌した後、さらにクロロ白金酸100mgを加えて、100℃で5時間反応させた。これを室温まで冷却させた後、ピリジン158gを加え撹拌しながら、エタノール138gを滴下して加えた。滴下後、室温で3時間反応させた後、生成した塩を濾別し、濾液を分留することで、1,1,1,4,4-ペンタエトキシ-1,4-ジシラヘキサンを220g(収率65%)得た。GC法で得られた純度は99.0%であった。また、残存水分量は185ppm、ケイ素、炭素、酸素、および水素以外の元素の含有量(金属不純物含有量)は、Na=1.2ppb、K=1.1ppb、Fe=1.7ppbであり、Li、Mg、Cr、Ag、Cu、Zn、Mn、Co、Ni、Ti、Zr、Al、Pb、Sn、W、Ptの各元素は検出限界値(0.2ppb)以下であった。以上の結果より、本合成例で得られた有機シラン化合物は、絶縁膜形成材料としての十分な純度を備えていることが確認された。
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、フラスコ内にトルエン500mlを加え、室温で撹拌しながらエチルジクロロシラン129gおよびビニルジエチルクロロシラン149gを加えた。しばらく撹拌し、ここにクロロ白金酸100mgを加え、100℃で5時間反応させた。これを室温まで冷却させたのち、ピリジン238gを加え撹拌しながら、エタノール140gを滴下して加えた。滴下後室温で3時間反応後、生成した塩を濾別し、濾液を分留することで、3,3,6-トリエトキシ-6-エチル-3,6-ジシラオクタン215g(収率70%)を得た。GC法で得られた純度は99.4%であった。また、残存水分量は45ppm、ケイ素、炭素、酸素、および水素以外の元素の含有量(金属不純物含有量)は、Na=1.8ppb、K=1.1ppb、Fe=1.3ppbであり、Li、Mg、Cr、Ag、Cu、Zn、Mn、Co、Ni、Ti、Zr、Al、Pb、Sn、W、Ptの各元素は検出限界値(0.2ppb)以下であった。以上の結果より、本合成例で得られた有機シラン化合物は、絶縁膜形成材料としての十分な純度を備えていることが確認された。
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、フラスコ内にトルエン500mlを加え、室温で撹拌しながらトリクロロシラン135gおよびエチルビニルエトキシシラン130gを加えた。しばらく撹拌し、ここにクロロ白金酸100mgを加え、100℃で5時間反応させた。これを室温まで冷却させたのち、ピリジン158gを加え撹拌しながら、エタノール138gを滴下して加えた。滴下後室温で3時間反応後、生成した塩を濾別し、濾液を分留することで、1、1,1,4-テトラエトキシ-1,4-ジシラヘキサン190g(収率65%)を得た。GC法で得られた純度は99.0%であった。また、残存水分量は185ppm、ケイ素、炭素、酸素、および水素以外の元素の含有量(金属不純物含有量)は、Na=1.2ppb、K=1.1ppb、Fe=1.7ppbであり、Li、Mg、Cr、Ag、Cu、Zn、Mn、Co、Ni、Ti、Zr、Al、Pb、Sn、W、Ptの各元素は検出限界値(0.2ppb)以下であった。以上の結果より、本合成例で得られた有機シラン化合物は、絶縁膜形成材料としての十分な純度を備えていることが確認された。
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60%)で得た。GC法で得られた純度は99.4%であった。また、残存水分量は120ppm、ケイ素、炭素、酸素、および水素以外の元素の含有量(金属不純物含有量)は、Na=1.2ppb、K=1.5ppb、Fe=1.1ppbであり、Li、Mg、Cr、Ag、Cu、Zn、Mn、Co、Ni、Ti、Zr、Al、Pb、Sn、W、Ptの各元素は検出限界値(0.2ppb)以下であった。以上の結果より、本合成例で得られた有機シラン化合物は、絶縁膜形成材料としての十分な純度を備えていることが確認された。
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)メチルジビニルシラン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)メチルジビニルシラン48g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およびテトラメトキシシラン115g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、[(メチルジビニルシリル)メチル]トリメトキシシラン76g(収率65%)で得た。GC法で得られた純度は99.3%であった。また、残存水分量は116ppm、ケイ素、炭素、酸素、および水素以外の元素の含有量(金属不純物含有量)は、Na=1.9ppb、K=2.1ppb、Fe=2.0ppbであり、Li、Mg、Cr、Ag、Cu、Zn、Mn、Co、Ni、Ti、Zr、Al、Pb、Sn、W、Ptの各元素は検出限界値(0.2ppb)以下であった。以上の結果より、本合成例で得られた有機シラン化合物は、絶縁膜形成材料としての十分な純度を備えていることが確認された。
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THF500mlおよび1,2-ビス(トリエトキシシリル)ビニレン353gを加え、室温で撹拌しながらエチルマグネシウムブロミドの1mol/LのTHF溶液を2L加えた。60℃で5時間反応させた後、これを室温まで冷却してから生成した塩を濾別し、濾液を分留することで、1,2-ビス(ジエトキシエチルシリル)ビニレン161g(収率50%)を得た。GC法で得られた純度は98.2%であった。また、残存水分量は88ppm、ケイ素、炭素、酸素、および水素以外の元素の含有量(金属不純物含有量)は、Na=1.2ppb、K=1.7ppb、Fe=1.0ppbであり、Li、Mg、Cr、Ag、Cu、Zn、Mn、Co、Ni、Ti、Zr、Al、Pb、Sn、W、Ptの各元素は検出限界値(0.2ppb)以下であった。以上の結果より、本合成例で得られた有機シラン化合物は、絶縁膜形成用材料としての十分な純度を備えていることが確認された。
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、フラスコ内にトルエン500mlを加え、室温で撹拌しながらエチルジクロロシラン129gおよびビニルトリエチルシラン142gを加えた。しばらく撹拌し、ここにクロロ白金酸100mgを加え、100度で5時間反応させた。これを室温まで冷却させたのち、ピリジン160gを加え撹拌しながら、エタノール100gを滴下して加えた。滴下後室温で3時間反応後、生成した塩を濾別し、濾液を分留することで、[(トリエチルシリル)エチル]エチルジエトキシシラン180g(化合物Cと標記、収率62%)を得た。GC法で得られた純度は99.2%であった。また、残存水分量は95ppm、ケイ素、炭素、酸素、および水素以外の元素の含有量(金属不純物含有量)は、Na=1.6ppb、K=1.1ppb、Fe=1.8ppbであり、Li、Mg、Cr、Ag、Cu、Zn、Mn、Co、Ni、Ti、Zr、Al、Pb、Sn、W、Ptの各元素は検出限界値(0.2ppb)以下であった。以上の結果より、本合成例で得られた有機シラン化合物は、絶縁膜形成材料としての十分な純度を備えていることが確認された。
5.3.1.実施例1
ユーテック社製2周波プラズマCVD装置を用い、シリカ源としてビス(トリメトキシシリル)メタン(ガス流量:0.3sccm)を用い、空孔形成剤としてビシクロ-(2.2.1)-ヘプタ-2,5-ジエン(ガス流量:0.6sccm)を用い、Arのガス流量100sccm、RF上部シャワーヘッド電力300W(27.12MHz)、下部基板電力150W(380kHz)、基板温度300℃、反応圧力10Torrとして、シリコン基板上にケイ素含有絶縁膜0.5μmを成膜した。
実施例1と同一の装置を用い、シリカ源として合成例1で合成したビス(ジメトキシメチルシリル)メタンとした以外は実施例1と同一条件にて、シリコン基板上にケイ素含有膜0.5μmを成膜した。
実施例1と同一の装置を用い、シリカ源として合成例2で合成した1,1,3,3-テトラメトキシ-1,3-ジシラブタンを用いたこと、及びO2ガスをガス流量1.0sccmで供給したこと以外は実施例1と同一条件にて、シリコン基板上にケイ素含有膜0.5μmを成膜した。
実施例1と同一の装置を用い、シリカ源として合成例3で合成したビス(ジメトキシシリル)メタンを用いたこと、及びO2ガスをガス流量1.0sccmで供給したこと以外は実施例1と同一条件にて、シリコン基板上にケイ素含有膜0.5μmを成膜した。
ユーテック社製2周波プラズマCVD装置を用い、シリカ源として合成例4で合成した1,1,1,3,3-ペンタメトキシ-1,3-ジシラブタン(ガス流量:0.3sccm)を用い、また、空孔形成剤としてビシクロ-[2.2.1]-ヘプタ-2,5-ジエン(ガス流量:0.6sccm)を用い、Arのガス流量100sccm、RF上部シャワーヘッド電力300W(27.12MHz)、下部基板電力150W(380kHz)、基板温度300℃、および反応圧力10Torrとして、シリコン基板上にケイ素含有絶縁膜0.5μmを成膜した。
ユーテック社製2周波プラズマCVD装置を用い、シリカ源として合成例5で得られた2,2,4-トリメトキシ-4-メチル-2,4-ジシラペンタンを用いこのガス流量を0.3sccm、また空孔形成剤としてビシクロ-[2.2.1]-ヘプタ-2,5-ジエンを用いこのガス流量を0.6sccm、Arのガス流量100sccm、RF上部シャワーヘッド電力300W(27.12MHz)、下部基板電力150W(380kHz)、基板温度300℃、反応圧力10Torrとして、シリコン基板上にケイ素含有絶縁膜0.5μmを成膜した。
実施例6と同一の装置を用い、シリカ源としてメチルトリメトキシシランを用いた以外は実施例6と同一条件にて、シリコン基板上にケイ素含有絶縁膜0.5μmを成膜した。
実施例6と同一の装置を用い、シリカ源として、参考合成例1で得られた[(トリメチルシリル)メチル]メチルジメトキシシランを用いた以外は実施例6と同一条件にて、シリコン基板上にケイ素含有絶縁膜0.5μmを成膜した。
実施例1と同一の装置を用い、シリカ源として合成例6で合成したビス(ジメトキシビニルシリル)メタン(ガス流量:0.3sccm)を用い、空孔形成剤としてシクロペンテンオキシド(ガス流量:0.6sccm)を用いた以外は実施例1と同一条件にて、シリコン基板上にケイ素含有膜0.5μmを成膜した。
実施例5と同一の装置を用い、シリカ源として合成例7で合成した1,1,1,3,3-ペンタメトキシ-3-ビニル-1,3-ジシラプロパン、空孔形成剤としてシクロペンテンオキシドを用い、これらのガス流量を0.6sccmとした以外は実施例5と同一条件にて、シリコン基板上にケイ素含有膜0.5μmを成膜した。
実施例6と同一の装置を用い、シリカ源として合成例8で得られた1,1,1,3-テトラメトキシ-3,3-ジビニル-1,3-ジシラプロパン、また空孔形成剤としてシクロペンテンオキシドを用いこのガス流量を0.6sccmとした以外は実施例6と同一条件にて、シリコン基板上にケイ素含有絶縁膜0.5μmを成膜した。
実施例9と同一の装置を用い、シリカ源としてビニルトリメトキシシランを用いた以外は実施例11と同一条件にて、シリコン基板上にケイ素含有絶縁膜0.5μmを成膜した。
実施例9と同一の装置を用い、シリカ源として参考合成例2で得られた[(メチルジビニルシリル)メチル]トリメトキシシランを用いた以外は実施例11と同一条件にて、シリコン基板上にケイ素含有絶縁膜0.5μmを成膜した。
実施例1と同一の装置を用い、シリカ源として合成例9で合成した1,2-ビス(ジエトキシエチルシリル)エタン(ガス流量:0.3sccm)を用い、空孔形成剤としp-キシレン(ガス流量:0.6sccm)を用いた以外は実施例1と同一条件にて、シリコン基板上にケイ素含有膜0.5μmを成膜した。
実施例5と同一の装置を用い、シリカ源として合成例10で合成した1,1,1,4,4-ペンタエトキシ-1,4-ジシラヘキサン、空孔形成剤としてシクロペンテンオキシドを用い、これらのガス流量を0.6sccmとした以外は実施例5と同一条件にて、シリコン基板上にケイ素含有膜0.5μmを成膜した。
実施例6と同一の装置を用い、シリカ源として合成例11で得られた3,3,6-トリエトキシ-6-エチル-3,6-ジシラオクタン、また空孔形成剤としてp-キシレンを用いこのガス流量を0.6sccmとした以外は実施例6と同一条件にて、シリコン基板上にケイ素含有絶縁膜0.5μmを成膜した。
実施例6と同一の装置を用い、シリカ源として合成例12で合成した1,1,1,4-テトラエトキシ-1,4-ジシラヘキサンを用いたこと、空孔形成剤としてp-キシレンを用いこのガス流量を0.6sccmとしたこと、及びO2ガスをガス流量1.0sccmで供給したこと以外は実施例6と同一条件にて、シリコン基板上にケイ素含有膜0.5μmを成膜した。
実施例10と同一の装置を用い、シリカ源として参考合成例3で合成した1,2-ビス(ジエトキシエチルシリル)ビニレンを用いた以外は実施例10と同一条件にて、シリコン基板上にケイ素含有膜0.5μmを成膜した。
実施例12と同一の装置を用い、シリカ源として参考合成例4で得られた[(トリエチルシリル)エチル]エチルジエトキシシランを用いた以外は実施例3と同一条件にて、シリコン基板上にケイ素含有絶縁膜0.5μmを成膜した。
実施例1と同一の装置を用い、シリカ源として合成例1で合成したビス(ジメトキシメチルシリル)メタン(ガス流量;0.06sccm)及びジエトキシメチルシラン(ガス流量:0.24sccm)とした以外は実施例1と同一条件にて、シリコン基板上にケイ素含有膜0.5μmを成膜した。
実施例1と同一の装置を用い、シリカ源として合成例1で合成したビス(ジメトキシメチルシリル)メタン(ガス流量;0.24sccm)及びジエトキシメチルシラン(ガス流量:0.06sccm)とした以外は実施例1と同一条件にて、シリコン基板上にケイ素含有膜0.5μmを成膜した。
合成例1で合成したビス(ジメトキシメチルシリル)メタンとジエトキシメチルシランとを20:80のモル比で混合し、ビス(ジメトキシメチルシリル)メタン及びジエトキシメチルシランと空孔形成剤とを1:1の重量比で混合し、化学気相成長法用材料を調製した。実施例1と同一の装置を用い、シリカ源として、調製した化学気相成長法用材料を用いた以外は実施例1と同一条件にて、シリコン基板上にケイ素含有膜0.5μmを成膜した。
合成例1で合成したビス(ジメトキシメチルシリル)メタンとジエトキシメチルシランとを80:20のモル比で混合し、ビス(ジメトキシメチルシリル)メタン及びジエトキシメチルシランと空孔形成剤とを1:1の重量比で混合し、化学気相成長法用材料を調製した。実施例1と同一の装置を用い、シリカ源として、調製した化学気相成長法用材料を用いた以外は実施例1と同一条件にて、シリコン基板上にケイ素含有膜0.5μmを成膜した。
合成例1で合成したビス(ジメトキシメチルシリル)メタンとビシクロ-(2.2.1)-ヘプタ-2,5-ジエンとを1:1の重量比で混合し、化学気相成長法用材料を調製した。実施例1と同一の装置を用い、シリカ源として調製した化学気相成長法用材料(ガス流量:0.3sccm)を用い、Arのガス流量100sccm、RF上部シャワーヘッド電力300W(27.12MHz)、下部基板電力150W(380kHz)、基板温度300℃、反応圧力10Torrとして、シリコン基板上にケイ素含有絶縁膜0.5μmを成膜した。
実施例1~18および比較例1~6で得られたケイ素含有絶縁膜の評価結果を表1に示す。
Claims (14)
- m=m’である、請求項1記載の化学気相成長法用材料。
- m=m’=1または2である、請求項2に記載の化学気相成長法用材料。
- m=0でかつm’=1である、請求項1記載の化学気相成長法用材料。
- m=2でかつm’=0~1である、請求項1記載の化学気相成長法用材料。
- n=1である、請求項1ないし5のいずれかに記載の化学気相成長法用材料。
- ケイ素、炭素、酸素、および水素を含む絶縁膜を形成するために用いられる、請求項1ないし6のいずれかに記載の化学気相成長法用材料。
- ケイ素、炭素、酸素、および水素以外の元素の含有量が10ppb未満であり、かつ、含水分量が0.1%未満である、請求項1ないし7のいずれかに記載の化学気相成長法用材料。
- 請求項1ないし8のいずれかに記載の化学気相成長法用材料を用いて化学気相成長法により形成された、ケイ素含有絶縁膜。
- 請求項1ないし9のいずれかに記載の化学気相成長法用材料を化学気相成長法により基板に堆積させて堆積膜を形成する工程と、
前記堆積膜について、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種の硬化処理を行う工程と、
を含む、ケイ素含有絶縁膜の製造方法。 - 請求項1ないし9のいずれかに記載の化学気相成長法用材料と、空孔形成剤とを化学気相成長法により基板に供給して堆積膜を形成する工程を含む、ケイ素含有絶縁膜の製造方法。
- 請求項10または11に記載のケイ素含有絶縁膜の製造方法により得られる、ケイ素含有絶縁膜。
- -Si-(CH2)n-Si-O-部位(ここでnは1~3の整数を示す。)を含む、請求項9または12に記載のケイ素含有絶縁膜。
- 比誘電率が3.0以下である、請求項9、12および13のいずれかに記載のケイ素含有絶縁膜。
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WO2011103282A3 (en) * | 2010-02-17 | 2012-02-02 | L'air Liquide, Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude | VAPOR DEPOSITION METHODS OF SiCOH LOW-K FILMS |
CN102762763A (zh) * | 2010-02-17 | 2012-10-31 | 乔治洛德方法研究和开发液化空气有限公司 | SiCOH低K膜的气相沉积法 |
EP2536867A2 (en) * | 2010-02-17 | 2012-12-26 | L'Air Liquide Société Anonyme pour l'Etude et l'Exploitation des Procédés Georges Claude | VAPOR DEPOSITION METHODS OF SiCOH LOW-K FILMS |
EP2536867A4 (en) * | 2010-02-17 | 2013-07-10 | Air Liquide | METHODS FOR VACUUM EVAPORATION OF LOW-POTASSIUM SICOH FILMS |
CN102762763B (zh) * | 2010-02-17 | 2014-12-31 | 乔治洛德方法研究和开发液化空气有限公司 | SiCOH低K膜的气相沉积法 |
US8932674B2 (en) | 2010-02-17 | 2015-01-13 | American Air Liquide, Inc. | Vapor deposition methods of SiCOH low-k films |
JP2013539225A (ja) * | 2010-09-22 | 2013-10-17 | ダウ コーニング コーポレーション | 電子物品及びその形成方法 |
JP2020513680A (ja) * | 2016-11-02 | 2020-05-14 | バーサム マテリアルズ ユーエス,リミティド ライアビリティ カンパニー | 高密度osg膜用シリル架橋アルキル化合物の使用 |
JP7465256B2 (ja) | 2018-08-29 | 2024-04-10 | アプライド マテリアルズ インコーポレイテッド | 非uv高硬度低kの膜堆積 |
Also Published As
Publication number | Publication date |
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EP2264219A4 (en) | 2012-09-05 |
JPWO2009119583A1 (ja) | 2011-07-28 |
CN101939465A (zh) | 2011-01-05 |
TW200948821A (en) | 2009-12-01 |
EP2264219A1 (en) | 2010-12-22 |
KR20100126327A (ko) | 2010-12-01 |
US20110042789A1 (en) | 2011-02-24 |
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