JP6937799B2 - ジアミノシラン化合物 - Google Patents
ジアミノシラン化合物 Download PDFInfo
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- JP6937799B2 JP6937799B2 JP2019126265A JP2019126265A JP6937799B2 JP 6937799 B2 JP6937799 B2 JP 6937799B2 JP 2019126265 A JP2019126265 A JP 2019126265A JP 2019126265 A JP2019126265 A JP 2019126265A JP 6937799 B2 JP6937799 B2 JP 6937799B2
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- -1 Diaminosilane compound Chemical class 0.000 title claims description 55
- 150000001875 compounds Chemical class 0.000 claims description 503
- 125000000217 alkyl group Chemical group 0.000 claims description 83
- 238000000034 method Methods 0.000 claims description 83
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 72
- 238000004519 manufacturing process Methods 0.000 claims description 50
- 239000011541 reaction mixture Substances 0.000 claims description 47
- 238000006243 chemical reaction Methods 0.000 claims description 35
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- 230000015572 biosynthetic process Effects 0.000 claims description 22
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 19
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 19
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 18
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 18
- 239000003054 catalyst Substances 0.000 claims description 13
- 238000003786 synthesis reaction Methods 0.000 claims description 12
- QDIFJLCNTFASPB-UHFFFAOYSA-N N-[[di(propan-2-yl)amino]-trisilylsilylsilyl]-N-propan-2-ylpropan-2-amine Chemical compound C(C)(C)N([SiH]([Si]([SiH3])([SiH3])[SiH3])N(C(C)C)C(C)C)C(C)C QDIFJLCNTFASPB-UHFFFAOYSA-N 0.000 claims description 5
- UREWCYFTAAFREV-UHFFFAOYSA-N N-[[di(propan-2-yl)amino]silyl-disilylsilyl]silyl-N-propan-2-ylpropan-2-amine Chemical compound C(C)(C)N([SiH2][Si]([SiH2]N(C(C)C)C(C)C)([SiH3])[SiH3])C(C)C UREWCYFTAAFREV-UHFFFAOYSA-N 0.000 claims description 5
- 230000008859 change Effects 0.000 claims description 4
- GYUXJBMTWCQENS-UHFFFAOYSA-N N-[[di(propan-2-yl)amino]-[disilyl(trisilylsilylsilyl)silyl]silyl]-N-propan-2-ylpropan-2-amine Chemical compound C(C)(C)N([SiH]([Si]([SiH2][Si]([SiH3])([SiH3])[SiH3])([SiH3])[SiH3])N(C(C)C)C(C)C)C(C)C GYUXJBMTWCQENS-UHFFFAOYSA-N 0.000 claims 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 168
- 229910052710 silicon Inorganic materials 0.000 description 143
- 239000000203 mixture Substances 0.000 description 115
- 239000010703 silicon Substances 0.000 description 103
- 125000003342 alkenyl group Chemical group 0.000 description 82
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 79
- 125000000304 alkynyl group Chemical group 0.000 description 74
- 239000000463 material Substances 0.000 description 61
- 239000002243 precursor Substances 0.000 description 61
- 125000002947 alkylene group Chemical group 0.000 description 55
- 229910052799 carbon Inorganic materials 0.000 description 39
- 238000004817 gas chromatography Methods 0.000 description 39
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 36
- 239000010409 thin film Substances 0.000 description 35
- RCHDLLHCJVFUEJ-UHFFFAOYSA-N N-[di(propan-2-yl)amino]silylsilylsilyl-N-propan-2-ylpropan-2-amine Chemical compound C(C)(C)N([SiH2][SiH2][SiH2]N(C(C)C)C(C)C)C(C)C RCHDLLHCJVFUEJ-UHFFFAOYSA-N 0.000 description 32
- 239000000460 chlorine Substances 0.000 description 30
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 30
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 26
- 229910052581 Si3N4 Inorganic materials 0.000 description 25
- 230000009467 reduction Effects 0.000 description 25
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 25
- 238000004518 low pressure chemical vapour deposition Methods 0.000 description 24
- 229910052757 nitrogen Inorganic materials 0.000 description 23
- 229910052801 chlorine Inorganic materials 0.000 description 22
- 229910052760 oxygen Inorganic materials 0.000 description 22
- 239000007789 gas Substances 0.000 description 21
- 229910052794 bromium Inorganic materials 0.000 description 20
- 239000006227 byproduct Substances 0.000 description 20
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 238000000151 deposition Methods 0.000 description 17
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 16
- 125000005843 halogen group Chemical group 0.000 description 16
- 239000001301 oxygen Substances 0.000 description 16
- 238000009835 boiling Methods 0.000 description 15
- 229910052740 iodine Inorganic materials 0.000 description 15
- 239000007788 liquid Substances 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 229910010082 LiAlH Inorganic materials 0.000 description 14
- 229910052814 silicon oxide Inorganic materials 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 13
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 13
- 229910052744 lithium Inorganic materials 0.000 description 13
- 238000000926 separation method Methods 0.000 description 13
- 229910052708 sodium Inorganic materials 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
- 238000006467 substitution reaction Methods 0.000 description 13
- 239000000758 substrate Substances 0.000 description 13
- 239000013626 chemical specie Substances 0.000 description 12
- 238000005229 chemical vapour deposition Methods 0.000 description 12
- 230000008021 deposition Effects 0.000 description 12
- 229910052739 hydrogen Inorganic materials 0.000 description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 12
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 12
- 229910000077 silane Inorganic materials 0.000 description 12
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 12
- 229910010271 silicon carbide Inorganic materials 0.000 description 12
- 238000007740 vapor deposition Methods 0.000 description 12
- 229910014299 N-Si Inorganic materials 0.000 description 11
- 230000008901 benefit Effects 0.000 description 11
- 239000012159 carrier gas Substances 0.000 description 11
- 229930195733 hydrocarbon Natural products 0.000 description 11
- 150000002430 hydrocarbons Chemical class 0.000 description 11
- 229910052700 potassium Inorganic materials 0.000 description 11
- 239000000376 reactant Substances 0.000 description 11
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 11
- 235000012431 wafers Nutrition 0.000 description 11
- 239000004215 Carbon black (E152) Substances 0.000 description 10
- 239000002210 silicon-based material Substances 0.000 description 10
- 239000002002 slurry Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 229910052782 aluminium Inorganic materials 0.000 description 9
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 9
- JJWOAHBIAVECNC-UHFFFAOYSA-N N-[[di(propan-2-yl)amino]-disilylsilyl]-N-propan-2-ylpropan-2-amine Chemical compound C(C)(C)N([Si]([SiH3])([SiH3])N(C(C)C)C(C)C)C(C)C JJWOAHBIAVECNC-UHFFFAOYSA-N 0.000 description 8
- 125000004429 atom Chemical group 0.000 description 8
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 150000005215 alkyl ethers Chemical class 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 238000000231 atomic layer deposition Methods 0.000 description 7
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 238000000623 plasma-assisted chemical vapour deposition Methods 0.000 description 7
- 150000004756 silanes Chemical class 0.000 description 7
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000012298 atmosphere Substances 0.000 description 6
- 239000002131 composite material Substances 0.000 description 6
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 6
- 229910052734 helium Inorganic materials 0.000 description 6
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000004065 semiconductor Substances 0.000 description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 5
- AZSNLCLFMMBPNG-UHFFFAOYSA-N N-[[di(propan-2-yl)amino]-(disilanyl)silyl]-N-propan-2-ylpropan-2-amine Chemical compound C(C)(C)N([SiH]([SiH2][SiH3])N(C(C)C)C(C)C)C(C)C AZSNLCLFMMBPNG-UHFFFAOYSA-N 0.000 description 5
- FXFWGDPDBSBPDV-UHFFFAOYSA-N N-[[di(propan-2-yl)amino]-(disilanyl)silyl]silyl-N-propan-2-ylpropan-2-amine Chemical compound C(C)(C)N([SiH2][SiH]([SiH2][SiH3])N(C(C)C)C(C)C)C(C)C FXFWGDPDBSBPDV-UHFFFAOYSA-N 0.000 description 5
- NIXWLJFSGWCMDP-UHFFFAOYSA-N N-[[di(propan-2-yl)amino]-silylsilyl]silyl-N-propan-2-ylpropan-2-amine Chemical compound C(C)(C)N([SiH2][SiH]([SiH3])N(C(C)C)C(C)C)C(C)C NIXWLJFSGWCMDP-UHFFFAOYSA-N 0.000 description 5
- LTGGLUXAIWFYQB-UHFFFAOYSA-N N-[[di(propan-2-yl)amino]-silylsilyl]silylsilyl-N-propan-2-ylpropan-2-amine Chemical compound C(C)(C)N([SiH2][SiH2][SiH]([SiH3])N(C(C)C)C(C)C)C(C)C LTGGLUXAIWFYQB-UHFFFAOYSA-N 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 229910052791 calcium Inorganic materials 0.000 description 5
- 239000011575 calcium Substances 0.000 description 5
- 239000008139 complexing agent Substances 0.000 description 5
- FIRQYUPQXNPTKO-UHFFFAOYSA-N ctk0i2755 Chemical class N[SiH2]N FIRQYUPQXNPTKO-UHFFFAOYSA-N 0.000 description 5
- PZPGRFITIJYNEJ-UHFFFAOYSA-N disilane Chemical compound [SiH3][SiH3] PZPGRFITIJYNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 229910052733 gallium Inorganic materials 0.000 description 5
- 229910052732 germanium Inorganic materials 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 239000001307 helium Substances 0.000 description 5
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052749 magnesium Inorganic materials 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 230000009257 reactivity Effects 0.000 description 5
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 5
- 229910052712 strontium Inorganic materials 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- LQIIEHBULBHJKX-UHFFFAOYSA-N 2-methylpropylalumane Chemical compound CC(C)C[AlH2] LQIIEHBULBHJKX-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- HRHFGXVQDFYEQT-UHFFFAOYSA-N C(C)(C)N([Si]([Si]([Si](N(C(C)C)C(C)C)(Cl)Cl)(Cl)Cl)(Cl)Cl)C(C)C Chemical compound C(C)(C)N([Si]([Si]([Si](N(C(C)C)C(C)C)(Cl)Cl)(Cl)Cl)(Cl)Cl)C(C)C HRHFGXVQDFYEQT-UHFFFAOYSA-N 0.000 description 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- AZDYPHQJYOZRMP-UHFFFAOYSA-N N-[di(propan-2-yl)amino]silylsilylsilylsilyl-N-propan-2-ylpropan-2-amine Chemical compound C(C)(C)N([SiH2][SiH2][SiH2][SiH2]N(C(C)C)C(C)C)C(C)C AZDYPHQJYOZRMP-UHFFFAOYSA-N 0.000 description 4
- GKRJAVMMCMOODQ-UHFFFAOYSA-N N-[di(propan-2-yl)amino]silylsilylsilylsilylsilyl-N-propan-2-ylpropan-2-amine Chemical compound C(C)(C)N([SiH2][SiH2][SiH2][SiH2][SiH2]N(C(C)C)C(C)C)C(C)C GKRJAVMMCMOODQ-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 description 4
- 229910052790 beryllium Inorganic materials 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical group OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 229910052793 cadmium Inorganic materials 0.000 description 4
- 229910052792 caesium Inorganic materials 0.000 description 4
- 229910052805 deuterium Inorganic materials 0.000 description 4
- MGDOJPNDRJNJBK-UHFFFAOYSA-N ethylaluminum Chemical compound [Al].C[CH2] MGDOJPNDRJNJBK-UHFFFAOYSA-N 0.000 description 4
- 150000004678 hydrides Chemical class 0.000 description 4
- 229910052738 indium Inorganic materials 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 229910052745 lead Inorganic materials 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- NRQNMMBQPIGPTB-UHFFFAOYSA-N methylaluminum Chemical compound [CH3].[Al] NRQNMMBQPIGPTB-UHFFFAOYSA-N 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 229910052701 rubidium Inorganic materials 0.000 description 4
- 229910052711 selenium Inorganic materials 0.000 description 4
- 238000002791 soaking Methods 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- 229910052714 tellurium Inorganic materials 0.000 description 4
- 229910052716 thallium Inorganic materials 0.000 description 4
- 229910052718 tin Inorganic materials 0.000 description 4
- VEDJZFSRVVQBIL-UHFFFAOYSA-N trisilane Chemical compound [SiH3][SiH2][SiH3] VEDJZFSRVVQBIL-UHFFFAOYSA-N 0.000 description 4
- 238000005292 vacuum distillation Methods 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- GNZBDLMUHMACNZ-UHFFFAOYSA-N N-(disilanyl)-N-propan-2-ylpropan-2-amine Chemical compound CC(C)N([SiH2][SiH3])C(C)C GNZBDLMUHMACNZ-UHFFFAOYSA-N 0.000 description 3
- QLBOOLDBZRQKTJ-UHFFFAOYSA-N N-(disilanylsilyl)-N-propan-2-ylpropan-2-amine Chemical compound CC(C)N([SiH2][SiH2][SiH3])C(C)C QLBOOLDBZRQKTJ-UHFFFAOYSA-N 0.000 description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 125000006193 alkinyl group Chemical group 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 229910052785 arsenic Inorganic materials 0.000 description 3
- LUXIMSHPDKSEDK-UHFFFAOYSA-N bis(disilanyl)silane Chemical compound [SiH3][SiH2][SiH2][SiH2][SiH3] LUXIMSHPDKSEDK-UHFFFAOYSA-N 0.000 description 3
- 229910052797 bismuth Inorganic materials 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000001975 deuterium Chemical group 0.000 description 3
- 229940043279 diisopropylamine Drugs 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 3
- 238000000427 thin-film deposition Methods 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- CLFRRBZBSCVBEA-UHFFFAOYSA-N C(C)(C)N([Si]([Si](Br)(Br)Br)([Si](Br)(Br)Br)N(C(C)C)C(C)C)C(C)C Chemical compound C(C)(C)N([Si]([Si](Br)(Br)Br)([Si](Br)(Br)Br)N(C(C)C)C(C)C)C(C)C CLFRRBZBSCVBEA-UHFFFAOYSA-N 0.000 description 2
- NSBRKWJYMBHYLV-UHFFFAOYSA-N C(C)(C)N([Si]([Si]([Si](Br)(Br)Br)(Br)Br)(N(C(C)C)C(C)C)Br)C(C)C Chemical compound C(C)(C)N([Si]([Si]([Si](Br)(Br)Br)(Br)Br)(N(C(C)C)C(C)C)Br)C(C)C NSBRKWJYMBHYLV-UHFFFAOYSA-N 0.000 description 2
- LRDGFKFGLFNXES-UHFFFAOYSA-N C(C)(C)N([Si]([Si]([Si](Br)(Br)Br)(N(C(C)C)C(C)C)Br)(Br)Br)C(C)C Chemical compound C(C)(C)N([Si]([Si]([Si](Br)(Br)Br)(N(C(C)C)C(C)C)Br)(Br)Br)C(C)C LRDGFKFGLFNXES-UHFFFAOYSA-N 0.000 description 2
- FNSVNDHCHMONNC-UHFFFAOYSA-N C(C)(C)N([Si]([Si]([Si](Cl)(Cl)Cl)(Cl)Cl)(N(C(C)C)C(C)C)Cl)C(C)C Chemical compound C(C)(C)N([Si]([Si]([Si](Cl)(Cl)Cl)(Cl)Cl)(N(C(C)C)C(C)C)Cl)C(C)C FNSVNDHCHMONNC-UHFFFAOYSA-N 0.000 description 2
- HEOOMEISOBVQOO-UHFFFAOYSA-N C(C)(C)N([Si]([Si]([Si](Cl)(Cl)Cl)(N(C(C)C)C(C)C)Cl)(Cl)Cl)C(C)C Chemical compound C(C)(C)N([Si]([Si]([Si](Cl)(Cl)Cl)(N(C(C)C)C(C)C)Cl)(Cl)Cl)C(C)C HEOOMEISOBVQOO-UHFFFAOYSA-N 0.000 description 2
- LYBPGKSVUAOSQZ-UHFFFAOYSA-N C(C)(C)N([Si]([Si]([Si](N(C(C)C)C(C)C)(Br)Br)(Br)Br)(Br)Br)C(C)C Chemical compound C(C)(C)N([Si]([Si]([Si](N(C(C)C)C(C)C)(Br)Br)(Br)Br)(Br)Br)C(C)C LYBPGKSVUAOSQZ-UHFFFAOYSA-N 0.000 description 2
- ZJCVMXSFPQETNX-UHFFFAOYSA-N C(C)(C)N([Si]([Si]([Si]([Si](Br)(Br)Br)(Br)Br)(N(C(C)C)C(C)C)Br)(Br)Br)C(C)C Chemical compound C(C)(C)N([Si]([Si]([Si]([Si](Br)(Br)Br)(Br)Br)(N(C(C)C)C(C)C)Br)(Br)Br)C(C)C ZJCVMXSFPQETNX-UHFFFAOYSA-N 0.000 description 2
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- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 150000004681 metal hydrides Chemical class 0.000 description 1
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- ACXIAEKDVUJRSK-UHFFFAOYSA-N methyl(silyloxy)silane Chemical compound C[SiH2]O[SiH3] ACXIAEKDVUJRSK-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- TWVSWDVJBJKDAA-UHFFFAOYSA-N n-[bis(dimethylamino)silyl]-n-methylmethanamine Chemical class CN(C)[SiH](N(C)C)N(C)C TWVSWDVJBJKDAA-UHFFFAOYSA-N 0.000 description 1
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- 238000001289 rapid thermal chemical vapour deposition Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
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- 239000005368 silicate glass Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- KPDAXQGRAPSFRK-UHFFFAOYSA-N trichloro(trichlorosilylsilyl)silane Chemical compound Cl[Si](Cl)(Cl)[SiH2][Si](Cl)(Cl)Cl KPDAXQGRAPSFRK-UHFFFAOYSA-N 0.000 description 1
- KPXBRKFCHBUVLL-UHFFFAOYSA-N trisilyl(trisilylsilylsilyl)silane Chemical compound [SiH3][Si]([SiH3])([SiH3])[SiH2][Si]([SiH3])([SiH3])[SiH3] KPXBRKFCHBUVLL-UHFFFAOYSA-N 0.000 description 1
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Classifications
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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
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
-
- 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
- C07F7/12—Organo silicon halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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Description
(R1R2N)SinH2n(NR3R4)(I)
[式中、下付き文字nは、3〜9の整数であり、R1は、メチル、プロピル、ブチル、ペンチル、ヘキシル、(C3〜C6)シクロアルキル、(C2〜C6)アルケニル、(C2〜C6)アルキニル、若しくはフェニルであり、R2、R3、及びR4は、それぞれ独立に、(C1〜C6)アルキル、(C3〜C6)シクロアルキル、(C2〜C6)アルケニル、(C2〜C6)アルキニル、若しくはフェニルであるか;又は、R1は、Hであり、R2、R3、及びR4は、それぞれ独立に、(C1〜C6)アルキル、(C3〜C6)シクロアルキル、(C2〜C6)アルケニル、(C2〜C6)アルキニル、若しくはフェニルであるか;又は、R1及びR3は、Hであり、R2及びR4は、それぞれ独立に、(C1〜C6)アルキル、(C3〜C6)シクロアルキル、(C2〜C6)アルケニル、(C2〜C6)アルキニル、若しくはフェニルであるか;又は、R1及びR2は、共に結合して−R1a−R2a−となり、−R1a−R2a−は、(C2〜C5)アルキレンであり、R3及びR4は、それぞれ独立に、(C1〜C6)アルキル、(C3〜C6)シクロアルキル、(C2〜C6)アルケニル、(C2〜C6)アルキニル、若しくはフェニルであるか;又は、R1及びR2は、共に結合して−R1a−R2a−となり、−R1a−R2a−は、(C2〜C5)アルキレンであり、R3及びR4は、共に結合して−R3a−R4a−となり、−R3a−R4a−は、(C2〜C5)アルキレンであるか;又は、R1及びR3は、共に結合して−R1a−R3a−となり、−R1a−R3a−は、(C2〜C5)アルキレンであり、R2及びR4は、それぞれ独立に、(C1〜C6)アルキル、(C3〜C6)シクロアルキル、(C2〜C6)アルケニル、(C2〜C6)アルキニル、若しくはフェニルであり;R1R2N−基及び−NR3R4基は、式(I)の化合物において同一のケイ素原子に、若しくは異なるケイ素原子に結合している]
(R1R2N)SinX2n(NR3R4)(c1)
[式中、Xは、それぞれ独立に、Cl、Br、及びIから選択されるハロゲン原子であり、n、R2、R3、及びR4は、上記で定義したとおりである]を、水素化アルミニウムと接触させて式(I)の化合物及び少なくとも1種の反応副生成物の混合物を与えること、を含む、製造方法。
(R1R2N)SinH2n+1(d1)、
を式(d2)の化合物、
(HNR3R4)(d2)
[式中、n、R1、R2、R3、及びR4は、上記で定義したとおりである]と、典型元素触媒存在下で接触させて式(I)の化合物の反応混合物を与えること、を含む、製造方法。
(R1R2N)SinH2n(NR3R4)(I)
[式中、下付き文字nは、3〜9の整数であり、R1は、メチル、プロピル、ブチル、ペンチル、ヘキシル、(C3〜C6)シクロアルキル、(C2〜C6)アルケニル、(C2〜C6)アルキニル、若しくはフェニルであり、R2、R3、及びR4は、それぞれ独立に、(C1〜C6)アルキル、(C3〜C6)シクロアルキル、(C2〜C6)アルケニル、(C2〜C6)アルキニル、若しくはフェニルであるか;又は、R1は、Hであり、R2、R3、及びR4は、それぞれ独立に、(C1〜C6)アルキル、(C3〜C6)シクロアルキル、(C2〜C6)アルケニル、(C2〜C6)アルキニル、若しくはフェニルであるか;又は、R1及びR3は、Hであり、R2及びR4は、それぞれ独立に、(C1〜C6)アルキル、(C3〜C6)シクロアルキル、(C2〜C6)アルケニル、(C2〜C6)アルキニル、若しくはフェニルであるか;又は、R1及びR2は、共に結合して−R1a−R2a−となり、−R1a−R2a−は、(C2〜C5)アルキレンであり、R3及びR4は、それぞれ独立に、(C1〜C6)アルキル、(C3〜C6)シクロアルキル、(C2〜C6)アルケニル、(C2〜C6)アルキニル、若しくはフェニルであるか;又は、R1及びR2は、共に結合して−R1a−R2a−となり、−R1a−R2a−は、(C2〜C5)アルキレンであり、R3及びR4は、共に結合して−R3a−R4a−となり、−R3a−R4a−は、(C2〜C5)アルキレンであるか;又は、R1及びR3は、共に結合して−R1a−R3a−となり、−R1a−R3a−は、(C2〜C5)アルキレンであり、R2及びR4は、それぞれ独立に、(C1〜C6)アルキル、(C3〜C6)シクロアルキル、(C2〜C6)アルケニル、(C2〜C6)アルキニル、若しくはフェニルであり;R1R2N−基及び−NR3R4基は、式(I)の化合物において同一のケイ素原子に、若しくは異なるケイ素原子に結合している]
式(c1)の化合物、
(R1R2N)SinX2n(NR3R4)(c1)
[式中、Xは、それぞれ独立に、Cl、Br、及びIから選択されるハロゲン原子であり、n、R1、R2、R3、及びR4は、式(I)の上記態様のいずれか1つで定義したとおりである]を、水素化アルミニウムと接触させて式(I)の化合物と少なくとも1種の反応副生成物の混合物を与えること、を含む、製造方法である。この接触工程は、本明細書において便宜的に、還元接触工程と呼ばれる場合がある。
(R1R2N)SinH2n(NR3R4)(I)
[式中、下付き文字nは、3〜9であり、R1は、メチル、プロピル、ブチル、ペンチル、ヘキシル、(C3〜C6)シクロアルキル、(C2〜C6)アルケニル、(C2〜C6)アルキニル、若しくはフェニルであり、R2、R3、及びR4は、それぞれ独立に、(C1〜C6)アルキル、(C3〜C6)シクロアルキル、(C2〜C6)アルケニル、(C2〜C6)アルキニル、若しくはフェニルであるか、又は、R1は、Hであり、R2、R3、及びR4は、それぞれ独立に、(C1〜C6)アルキル、(C3〜C6)シクロアルキル、(C2〜C6)アルケニル、(C2〜C6)アルキニル、若しくはフェニルであるか、又は、R1及びR3は、Hであり、R2及びR4は、それぞれ独立に、(C1〜C6)アルキル、(C3〜C6)シクロアルキル、(C2〜C6)アルケニル、(C2〜C6)アルキニル、若しくはフェニルであるか、又は、R1及びR2は、共に結合して−R1a−R2a−となり、−R1a−R2a−は、(C2〜C5)アルキレンであり、R3及びR4は、それぞれ独立に、(C1〜C6)アルキル、(C3〜C6)シクロアルキル、(C2〜C6)アルケニル、(C2〜C6)アルキニル、若しくはフェニルであるか、又は、R1及びR2は、共に結合して−R1a−R2a−となり、−R1a−R2a−は、(C2〜C5)アルキレンであり、R3及びR4は、共に結合して−R3a−R4a−となり、−R3a−R4a−は、(C2〜C5)アルキレンであるか、又は、R1及びR3は、共に結合して−R1a−R3a−となり、−R1a−R3a−は、(C2〜C5)アルキレンであり、R2及びR4は、それぞれ独立に、(C1〜C6)アルキル、(C3〜C6)シクロアルキル、(C2〜C6)アルケニル、(C2〜C6)アルキニル、若しくはフェニルであり、R1R2N−基及び−NR3R4基は、式(I)の化合物において同一のケイ素原子に、又は異なるケイ素原子に結合している]、の製造方法であって、この方法は、式(d1)の化合物、(R1R2N)SinH2n+1(d1)、を式(d2)の化合物、(NR3R4)(d2)[式中、n、R1、R2、R3、及びR4は、上記で定義したとおりである]と、触媒存在下で接触させて反応混合物を与えることと[この触媒は、Li、Na、K、Rb、Cs、Be、Mg、Ca、Sr、Ba、B、Al、Ga、In、Tl、C、Si、Ge、Sn、Pb、N、P、As、Bb、Bi、O、S、Se、Te、F、Cl、Br、I、Zn、Cd、又はHgのうちの少なくとも1種の典型元素を含有する]、反応混合物を約0℃〜約250℃の温度に保つことと、反応を進行させて上記の式(I)の化合物を形成することと、反応混合物から式(I)の化合物の式(I)の化合物を分離することと、を含み、反応混合物の温度は、合成中に変化してもよく、反応混合物の温度が約0℃未満に低下しないように、かつ約250℃を超えないように保たれる、製造方法。
式(d1)の化合物、
(R1R2N)SinH2n+1(d1)、
を式(d2)の化合物、
(HNR3R4)(d2)[式中、n、R1、R2、R3、及びR4は、上記で定義したとおりである]と、触媒存在下で接触させて反応混合物を与えることと[この触媒は、Li、Na、K、Rb、Cs、Be、Mg、Ca、Sr、Ba、B、Al、Ga、In、Tl、C、Si、Ge、Sn、Pb、N、P、As、Bb、Bi、O、S、Se、Te、F、Cl、Br、I、Zn、Cd、又はHgのうちの少なくとも1種の典型元素を含有する]、
反応混合物を約0℃〜約250℃の温度に保つことと、
反応を進行させて上記の式(I)の化合物を形成することと、
反応混合物から式(I)の化合物の式(I)の化合物を分離することと、を含み、
反応混合物の温度は、合成中に変化してもよく、反応混合物の温度が約0℃未満に低下しないように、かつ約250℃を超えないように保たれる、製造方法である。
Claims (2)
- 式(I)の化合物
(R1R2N)SinH2n(NR3R4)(I)
[式中、下付き文字nは、5又は9であり、R1は、メチル、プロピル、ブチル、ペンチル、ヘキシル若しくは(C3〜C6)シクロアルキルであり、R2、R3、及びR4は、それぞれ独立に、(C1〜C6)アルキル若しくは(C3〜C6)シクロアルキルである]
の製造方法であって、前記方法は、
式SinH2n+2の化合物[式中、下付き文字nは、5又は9である]を式(d2)の化合物、(HNR3R4)(d2)[式中、R3及びR4は、上記で定義したとおりである]と、触媒存在下で接触させて反応混合物を与えることと[前記触媒は、B(C 6 F 5 ) 3 を含む]、
前記反応混合物を0℃〜250℃の温度に保つことと、
反応を進行させて上記の前記式(I)の化合物を形成することと、前記反応混合物から前記式(I)の化合物を分離することと、を含み、
前記反応混合物の温度は、合成中に変化してもよく、前記反応混合物の温度が0℃未満 に低下しないように、かつ250℃を超えないように保たれる、方法。 - 式(I)の化合物が、1,3−ビス(ジイソプロピルアミノ)−2,2−ジシリルトリシラン、1,1−ビス(ジイソプロピルアミノ)−2,2−ジシリルトリシラン、1,5−ビス(ジイソプロピルアミノ)−2,2,4,4−テトラシリルペンタシラン又は1,1−ビス(ジイソプロピルアミノ)−2,2,4,4−テトラシリルペンタシランから選択される、請求項1に記載の方法。
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