WO2008051328A1 - Composition comprising neopentasilane and method of preparing same - Google Patents
Composition comprising neopentasilane and method of preparing same Download PDFInfo
- Publication number
- WO2008051328A1 WO2008051328A1 PCT/US2007/019165 US2007019165W WO2008051328A1 WO 2008051328 A1 WO2008051328 A1 WO 2008051328A1 US 2007019165 W US2007019165 W US 2007019165W WO 2008051328 A1 WO2008051328 A1 WO 2008051328A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- neopentasilane
- silane
- composition
- tetrakis
- trihalosilyl
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 71
- 238000000034 method Methods 0.000 title claims abstract description 44
- 229910000077 silane Inorganic materials 0.000 claims abstract description 38
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims abstract description 34
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 claims abstract description 23
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 31
- 239000012970 tertiary amine catalyst Substances 0.000 claims description 18
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 14
- 239000010703 silicon Substances 0.000 claims description 13
- 229910052710 silicon Inorganic materials 0.000 claims description 13
- 229930195733 hydrocarbon Natural products 0.000 claims description 12
- 150000002430 hydrocarbons Chemical class 0.000 claims description 12
- 150000004756 silanes Chemical class 0.000 claims description 12
- LXEXBJXDGVGRAR-UHFFFAOYSA-N trichloro(trichlorosilyl)silane Chemical group Cl[Si](Cl)(Cl)[Si](Cl)(Cl)Cl LXEXBJXDGVGRAR-UHFFFAOYSA-N 0.000 claims description 6
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical group C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 239000003960 organic solvent Substances 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 11
- 238000004821 distillation Methods 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- HTCXJJZPNJOAGE-UHFFFAOYSA-N tetrakis(trichlorosilyl)silane Chemical compound Cl[Si](Cl)(Cl)[Si]([Si](Cl)(Cl)Cl)([Si](Cl)(Cl)Cl)[Si](Cl)(Cl)Cl HTCXJJZPNJOAGE-UHFFFAOYSA-N 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- -1 neopentasilane Chemical class 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- ASWZNPOTXAXUPB-UHFFFAOYSA-N tribromo(tribromosilyl)silane Chemical compound Br[Si](Br)(Br)[Si](Br)(Br)Br ASWZNPOTXAXUPB-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 229910003828 SiH3 Inorganic materials 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000010954 commercial manufacturing process Methods 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- OLRJXMHANKMLTD-UHFFFAOYSA-N silyl Chemical compound [SiH3] OLRJXMHANKMLTD-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 206010010144 Completed suicide Diseases 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- 229910003946 H3Si Inorganic materials 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- 229910052581 Si3N4 Inorganic materials 0.000 description 2
- 125000002015 acyclic group Chemical group 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 238000005229 chemical vapour deposition Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 230000002939 deleterious effect Effects 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 2
- 229910010271 silicon carbide Inorganic materials 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- QVCUKHQDEZNNOC-UHFFFAOYSA-N 1,2-diazabicyclo[2.2.2]octane Chemical compound C1CC2CCN1NC2 QVCUKHQDEZNNOC-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 238000005133 29Si NMR spectroscopy Methods 0.000 description 1
- 239000005046 Chlorosilane Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 1
- GSCCALZHGUWNJW-UHFFFAOYSA-N N-Cyclohexyl-N-methylcyclohexanamine Chemical compound C1CCCCC1N(C)C1CCCCC1 GSCCALZHGUWNJW-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- JIMODRYHNQDMSX-UHFFFAOYSA-N [GeH2].[Si] Chemical class [GeH2].[Si] JIMODRYHNQDMSX-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical class Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- DIOQZVSQGTUSAI-NJFSPNSNSA-N decane Chemical compound CCCCCCCCC[14CH3] DIOQZVSQGTUSAI-NJFSPNSNSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- QUZPNFFHZPRKJD-UHFFFAOYSA-N germane Chemical compound [GeH4] QUZPNFFHZPRKJD-UHFFFAOYSA-N 0.000 description 1
- 229910052986 germanium hydride Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 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
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- SRLHDBRENZFCIN-UHFFFAOYSA-N n,n-di(butan-2-yl)butan-2-amine Chemical compound CCC(C)N(C(C)CC)C(C)CC SRLHDBRENZFCIN-UHFFFAOYSA-N 0.000 description 1
- FRQONEWDWWHIPM-UHFFFAOYSA-N n,n-dicyclohexylcyclohexanamine Chemical compound C1CCCCC1N(C1CCCCC1)C1CCCCC1 FRQONEWDWWHIPM-UHFFFAOYSA-N 0.000 description 1
- NILJCGYQNXKIRL-UHFFFAOYSA-N n,n-dicyclopentylcyclopentanamine Chemical compound C1CCCC1N(C1CCCC1)C1CCCC1 NILJCGYQNXKIRL-UHFFFAOYSA-N 0.000 description 1
- QJEWDNDJRVJYBY-UHFFFAOYSA-N n,n-dicyclopropylcyclopropanamine Chemical compound C1CC1N(C1CC1)C1CC1 QJEWDNDJRVJYBY-UHFFFAOYSA-N 0.000 description 1
- PPMQPFXXZSFIKT-UHFFFAOYSA-N n,n-diethylcyclobutanamine Chemical compound CCN(CC)C1CCC1 PPMQPFXXZSFIKT-UHFFFAOYSA-N 0.000 description 1
- CIXSDMKDSYXUMJ-UHFFFAOYSA-N n,n-diethylcyclohexanamine Chemical compound CCN(CC)C1CCCCC1 CIXSDMKDSYXUMJ-UHFFFAOYSA-N 0.000 description 1
- ZURPXDWBEOCXSO-UHFFFAOYSA-N n,n-diethylcyclopentanamine Chemical compound CCN(CC)C1CCCC1 ZURPXDWBEOCXSO-UHFFFAOYSA-N 0.000 description 1
- NOCWSQZNTAOPPV-UHFFFAOYSA-N n,n-diethylcyclopropanamine Chemical compound CCN(CC)C1CC1 NOCWSQZNTAOPPV-UHFFFAOYSA-N 0.000 description 1
- DIAIBWNEUYXDNL-UHFFFAOYSA-N n,n-dihexylhexan-1-amine Chemical compound CCCCCCN(CCCCCC)CCCCCC DIAIBWNEUYXDNL-UHFFFAOYSA-N 0.000 description 1
- QDZNNDAHQZPZRK-UHFFFAOYSA-N n,n-dimethylcyclobutanamine Chemical compound CN(C)C1CCC1 QDZNNDAHQZPZRK-UHFFFAOYSA-N 0.000 description 1
- ZEFLPHRHPMEVPM-UHFFFAOYSA-N n,n-dimethylcyclopentanamine Chemical compound CN(C)C1CCCC1 ZEFLPHRHPMEVPM-UHFFFAOYSA-N 0.000 description 1
- DYVUNUQDYHPXSU-UHFFFAOYSA-N n,n-dimethylcyclopropanamine Chemical compound CN(C)C1CC1 DYVUNUQDYHPXSU-UHFFFAOYSA-N 0.000 description 1
- YWWNNLPSZSEZNZ-UHFFFAOYSA-N n,n-dimethyldecan-1-amine Chemical compound CCCCCCCCCCN(C)C YWWNNLPSZSEZNZ-UHFFFAOYSA-N 0.000 description 1
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 1
- LSICDRUYCNGRIF-UHFFFAOYSA-N n,n-dimethylheptan-1-amine Chemical compound CCCCCCCN(C)C LSICDRUYCNGRIF-UHFFFAOYSA-N 0.000 description 1
- QMHNQZGXPNCMCO-UHFFFAOYSA-N n,n-dimethylhexan-1-amine Chemical compound CCCCCCN(C)C QMHNQZGXPNCMCO-UHFFFAOYSA-N 0.000 description 1
- AMAADDMFZSZCNT-UHFFFAOYSA-N n,n-dimethylnonan-1-amine Chemical compound CCCCCCCCCN(C)C AMAADDMFZSZCNT-UHFFFAOYSA-N 0.000 description 1
- UQKAOOAFEFCDGT-UHFFFAOYSA-N n,n-dimethyloctan-1-amine Chemical compound CCCCCCCCN(C)C UQKAOOAFEFCDGT-UHFFFAOYSA-N 0.000 description 1
- OOHAUGDGCWURIT-UHFFFAOYSA-N n,n-dipentylpentan-1-amine Chemical compound CCCCCN(CCCCC)CCCCC OOHAUGDGCWURIT-UHFFFAOYSA-N 0.000 description 1
- CYQYCASVINMDFD-UHFFFAOYSA-N n,n-ditert-butyl-2-methylpropan-2-amine Chemical compound CC(C)(C)N(C(C)(C)C)C(C)(C)C CYQYCASVINMDFD-UHFFFAOYSA-N 0.000 description 1
- CTSROGJAZGEKAW-UHFFFAOYSA-N n-butan-2-yl-n-ethylbutan-2-amine Chemical compound CCC(C)N(CC)C(C)CC CTSROGJAZGEKAW-UHFFFAOYSA-N 0.000 description 1
- ZBGZVIGUXBTBGM-UHFFFAOYSA-N n-butan-2-yl-n-methylbutan-2-amine Chemical compound CCC(C)N(C)C(C)CC ZBGZVIGUXBTBGM-UHFFFAOYSA-N 0.000 description 1
- BBDGYADAMYMJNO-UHFFFAOYSA-N n-butyl-n-ethylbutan-1-amine Chemical compound CCCCN(CC)CCCC BBDGYADAMYMJNO-UHFFFAOYSA-N 0.000 description 1
- MTHFROHDIWGWFD-UHFFFAOYSA-N n-butyl-n-methylbutan-1-amine Chemical compound CCCCN(C)CCCC MTHFROHDIWGWFD-UHFFFAOYSA-N 0.000 description 1
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
- GJBZNKTZGJBGEB-UHFFFAOYSA-N n-cyclobutyl-n-ethylcyclobutanamine Chemical compound C1CCC1N(CC)C1CCC1 GJBZNKTZGJBGEB-UHFFFAOYSA-N 0.000 description 1
- IPPIEZBHYQSRIN-UHFFFAOYSA-N n-cyclobutyl-n-methylcyclobutanamine Chemical compound C1CCC1N(C)C1CCC1 IPPIEZBHYQSRIN-UHFFFAOYSA-N 0.000 description 1
- XRKQMIFKHDXFNQ-UHFFFAOYSA-N n-cyclohexyl-n-ethylcyclohexanamine Chemical compound C1CCCCC1N(CC)C1CCCCC1 XRKQMIFKHDXFNQ-UHFFFAOYSA-N 0.000 description 1
- CRYMTEHEKQNKEB-UHFFFAOYSA-N n-cyclopentyl-n-ethylcyclopentanamine Chemical compound C1CCCC1N(CC)C1CCCC1 CRYMTEHEKQNKEB-UHFFFAOYSA-N 0.000 description 1
- JNMBQGIZTCTCRT-UHFFFAOYSA-N n-cyclopentyl-n-methylcyclopentanamine Chemical compound C1CCCC1N(C)C1CCCC1 JNMBQGIZTCTCRT-UHFFFAOYSA-N 0.000 description 1
- TUIARJOYTDIVEH-UHFFFAOYSA-N n-cyclopropyl-n-ethylcyclopropanamine Chemical compound C1CC1N(CC)C1CC1 TUIARJOYTDIVEH-UHFFFAOYSA-N 0.000 description 1
- TXNBSTNWVSFRLH-UHFFFAOYSA-N n-cyclopropyl-n-methylcyclopropanamine Chemical compound C1CC1N(C)C1CC1 TXNBSTNWVSFRLH-UHFFFAOYSA-N 0.000 description 1
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 description 1
- XWCCTMBMQUCLSI-UHFFFAOYSA-N n-ethyl-n-propylpropan-1-amine Chemical compound CCCN(CC)CCC XWCCTMBMQUCLSI-UHFFFAOYSA-N 0.000 description 1
- POMGZMHIXYRARC-UHFFFAOYSA-N n-hexyl-n-methylhexan-1-amine Chemical compound CCCCCCN(C)CCCCCC POMGZMHIXYRARC-UHFFFAOYSA-N 0.000 description 1
- JJRDPNRWFSHHKJ-UHFFFAOYSA-N n-methyl-n-pentylpentan-1-amine Chemical compound CCCCCN(C)CCCCC JJRDPNRWFSHHKJ-UHFFFAOYSA-N 0.000 description 1
- ISRXMEYARGEVIU-UHFFFAOYSA-N n-methyl-n-propan-2-ylpropan-2-amine Chemical compound CC(C)N(C)C(C)C ISRXMEYARGEVIU-UHFFFAOYSA-N 0.000 description 1
- UVBMZKBIZUWTLV-UHFFFAOYSA-N n-methyl-n-propylpropan-1-amine Chemical compound CCCN(C)CCC UVBMZKBIZUWTLV-UHFFFAOYSA-N 0.000 description 1
- RBKXAWGOLUBYSU-UHFFFAOYSA-N n-tert-butyl-n,2-dimethylpropan-2-amine Chemical compound CC(C)(C)N(C)C(C)(C)C RBKXAWGOLUBYSU-UHFFFAOYSA-N 0.000 description 1
- OLDWDCDQSRUGAY-UHFFFAOYSA-N n-tert-butyl-n-ethyl-2-methylpropan-2-amine Chemical compound CCN(C(C)(C)C)C(C)(C)C OLDWDCDQSRUGAY-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000526 short-path distillation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 1
- 239000005052 trichlorosilane Substances 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B33/00—Silicon; Compounds thereof
- C01B33/04—Hydrides of silicon
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
- C08K5/5419—Silicon-containing compounds containing oxygen containing at least one Si—O bond containing at least one Si—C bond
Definitions
- the present invention relates to a composition comprising neopentasilane and more particularly to a composition comprising at least 93% (w/w) of neopentasilane.
- the present invention also relates to a method of preparing a composition comprising neopentasilane, the method comprising treating a tetrakis(trihalosilyl)silane with diisobutylaluminum hydride.
- Neopentasilane and methods of preparing the compound are known in the art.
- Feher et al. Inorg. Nucl. Chem. Lett. 1974, 10(7), 577-579) report the preparation of mixture of silanes, including neopentasilane, by acid decomposition of magnesium suicide and separation by distillation and gas chromatography.
- Andrews et al. J. Chem. Soc. A: Inorganic, Physical, Theoretical 1966, (1), 46-48) report the preparation of high molecular weight silicon-germanium hydrides using a silent electric discharge of 40 kV for 5-10 h in a conventional ozonizer tube maintained at -20 0 C.
- the present invention is directed to a composition
- a composition comprising: ⁇ at least 93% (w/w) of neopentasilane; not greater than 5% (w/w) of other silanes; and not greater than 2% (w/w) of hydrocarbons.
- the present invention is also directed to a method of preparing a composition comprising neopentasilane, the method comprising:
- the composition of the present invention contains neopentasilane in a state of high purity.
- the composition typically contains at least 93% (w/w) neopentasilane, not greater than 5% (w/w) of other silanes, and not greater than 2% (w/w) of hydrocarbons, based on the total weight of the composition.
- the method of the present invention produces neopentasilane having high purity in high yield.
- the neopentasilane can be readily and efficiently removed from the reaction mixture by distillation. This separation minimizes the occurrence of unwanted side reactions that diminish purity and yield.
- the neopentasilane is free of solvent, which can be deleterious in certain applications, especially in the electronics field.
- the method can be carried out economically with a stoichiometric amount or only slight excess of diisobutylaluminum hydride. Still further, the method can be scaled to a commercial manufacturing process.
- the neopentasilane of the present invention can be used as a precursor for the formation of silicon-containing films, such as silica, silicon carbide, and silicon nitride, by chemical or physical vapor deposition.
- a composition according to the present invention comprises: at least 93% (w/w) of neopentasilane; not greater than 5% (w/w) of other silanes; and not greater than 2% (w/w) of hydrocarbons.
- the composition comprises at least 93% (w/w), alternatively at least 95% (w/w), alternatively at least 98% (w/w), of neopentasilane, based on the total weight of the composition.
- the composition typically comprises 93 to 100% (w/w), alternatively from 95 to 99% (w/w), alternatively from 97 to 99% (w/w), alternatively from 99 to 99.9% (w/w), of neopentasilane.
- the composition comprises not greater than 5% (w/w), alternatively not greater than 3% (w/w), alternatively not greater than 1% (w/w), of at least one other silane, based on the total weight of the composition.
- other silanes include, but are not limited to, silanes having the following formulae: Si3Hg, Si4Hio > Si ⁇ Hi ⁇ Si7Hi6, iso-BuSiH3, H2(CH3)SiSi(SiH3)3, and H2(iso-Bu)SiSi(SiH3)3, where iso- Bu is isobutyl.
- the composition also comprises not greater than 2% (w/w), alternatively not greater than 1% (w/w), of at least one hydrocarbon, based on the total weight of the composition.
- hydrocarbons include, but are not limited to, aliphatic hydrocarbons such as isobutane, pentane, and hexanes; and aromatic hydrocarbons such as toluene.
- the weight percent of neopentasilane, other silane(s), and hydrocarbon(s) in the composition can be determined from the proton nuclear magnetic resonance ( ⁇ H NMR) spectrum of the composition as described below in the Examples section.
- a method of preparing a composition comprising neopentasilane comprises:
- step (iv) of the present method a hexahalodisilane having the formula X3SiSiX3, wherein X is -Cl or —Br, is treated with a tertiary amine catalyst to produce a first mixture comprising a tetrakis(trihalosilyl)silane and a silicon tetrahalide.
- the hexahalodisilane can be a single hexahalodisilane or a mixture comprising two or more different hexahalodisilanes.
- the hexahalodisilane can be hexachlorodisilane, hexabromodisilane, or a mixture of hexachlorodisilane and hexabromodisilane.
- Methods of preparing hexahalodisilanes are known in the art.
- hexachlorodisilane can be prepared by reacting silicon metal with hydrogen chloride and removing the product having a boiling point of 144-146 0 C.
- hexabromodisilane can be prepared by treating calcium suicide with oxygen and bromine gases and subsequently distilling the reaction products at 130-140 0 C under a pressure of 20 kPa to 27 kPa.
- hexabromodisilane can be prepared by reacting calcium silic ⁇ de with bromine, as exemplified by Walter C. Schumb (Inorg. Synth. II, 1946, 98-102).
- the tertiary amine catalyst can be a monoamine, diamine, triamine, or polyamine.
- the tertiary amine catalyst can have an acyclic, cyclic, or acyclic/cyclic structure.
- tertiary amine catalysts include, but are not limited to, monoamines, such as trimethylamine, triethylamine, tri-n-propylamine, triisopropylamine, tri-n-butylamine, tri-sec- butylamine, tri-tert-butylamine, tri-n-pentylamine, tri-n-hexylamine, N-methyldiethylamine.
- monoamines such as trimethylamine, triethylamine, tri-n-propylamine, triisopropylamine, tri-n-butylamine, tri-sec- butylamine, tri-tert-butylamine, tri-n-pentylamine, tri-n-hexylamine, N-methyldiethylamine.
- N-methyldi-n-propylamine N-methyldiisopropylamine, N-methyldi-n-butylamine, N- methyldi-sec-butylamine, N-methyldi-tert-butylamine, N-methyldi-n-pentylamine, N- methyldi-n-hexylamine, N,N-dimethylethylamine, N,N-di-n-propylethylamine, N,N- diisopropylethylamine, N,N-di-n-butylethylamine, N,N-di-sec-butylethylamine, N,N-di-tert- butylethylamine, N,N-dimethylhexylamine, N,N-dimethylheptylamine, N,N- dimethyloctylamine, N,N-dimethylnonylamine, N,N-dimethyldecyl
- the tertiary amine catalyst can be a single tertiary amine or a mixture comprising two or more different tertiary amines
- the hexahalodisilane can be treated with the tertiary amine catalyst in any Standard reactor suitable for contacting chlorosilanes with a tertiary amine.
- Suitable reactors include glass and Teflon-lined glass reactors.
- the reactor is equipped with a means of agitation, such as stirring.
- the reaction is carried out in an inert atmosphere, such as nitrogen or argon, in the absence of moisture.
- the hexahalodisilane and the tertiary amine catalyst can be combined in any order. Typically the tertiary amine catalyst is added to the hexahalodisilane with vigorous agitation. However, reverse addition, i.e. addition of the tetrakis(trihalosilyl)silane to the tertiary amine catalyst is also possible [0025]
- the rate of addition of the tertiary amine catalyst to the hexahalodisilane (or vice- versa) is typically such that the temperature of the reaction mixture remains below the decomposition temperature of the tetrakis(trihalosilyl)silane.
- the hexahalodisilane is typically treated with the tertiary amine catalyst at a temperature of -10 to 300 0 C, alternatively from 0 to 100 0 C, alternatively form 0 to 60 0 C, alternatively from 20 to 60 0 C.
- the temperature is above 300 0 C, the tetrakis- (trihalosilyl)silane is subject to decomposition.
- the reaction time depends on several factors, including the structures of the hexahalodisilane and the tertiary amine catalyst, and the temperature.
- the reaction time is typically from 1 to 24 h, alternatively from 1 to 12 h., alternatively from. 1 to 6 h, at a temperature of from 20 to 60 0 C.
- the optimum reaction time can be determined by routine experimentation using the methods set forth in the Examples section below.
- the concentration of the tertiary amine catalyst in the first reaction mixture is typically from 0.001 to 10% (w/w), alternatively from 0.01 to 1% (w/w), alternatively from 0.01 to 0.1% (w/w), based on the weight of the hexahalodisilane.
- Step (i) of the present method can be carried out either in the presence or absence of an organic solvent.
- the organic solvent can be any aprotic or dipolar aprotic organic solvent that does not react with the hexahalodisilane, the tertiary amine catalyst, or the tetrakis(trihalosilyl)silane product under the conditions of the present method.
- organic solvents include, but are not limited to, saturated aliphatic hydrocarbons such as n-pentane, hexane, n-heptane, isooctane and dodecane; cycloaliphatic hydrocarbons such as cyclopentane and cyclohexane; aromatic hydrocarbons such as benzene, toluene, xylene and mesitylene; ketones such as methyl isobutyl ketone (MIBK); halogenated alkanes such as trichloroethane; and halogenated aromatic hydrocarbons such as bromobenzene and chlorobenzene.
- the organic solvent can be a single organic solvent or a mixture comprising two or more different organic solvents, each as described and exemplified above.
- the concentration of the organic solvent is typically from 1 to 99% (w/w), alternatively from 10 to 99% (w/w), alternatively from 50 to 99% (w/w), alternatively from 50 to 75% (w/w), based on the total weight of the first reaction mixture.
- step (ii) of the present method the tetrakis(trihalosilyl)silane and the silicon tetrahalide are separated. The separation can be carried out by applying a vacuum to the mixture to remove the silicon tetrahalide and any organic solvent.
- the separation can be carried out by applying a vacuum of 1.3 Pa to the mixture at a temperature of 60 °C for 7 h and collecting the silicon tetrahalide and any solvent in a cold trap.
- the separated tetrakis(trihalosilyl)silane is treated with diisobutylaluminum hydride to produce a second mixture comprising neopentasilane.
- the diisobutylaluminum hydride is commercially available in liquid form neat or as a solution in various organic solvents. However, some solvents may distill with the neopentasilane in step (iv) of the method and contaminate the product. Such contamination can cause problems in certain applications, particularly in the electronics field, that require high purity.
- the tetrakis(trihalosilyl)silane can be treated with the diisobutylaluminum hydride in any standard reactor suitable for contacting a halosilane with a metal hydride reducing agent.
- Suitable reactors include glass and Teflon-lined glass reactors.
- the reactor is equipped with a means of agitation, such as stirring.
- the reaction is typically carried out in an inert atmosphere. This can be accomplished by purging the reactor with a dry inert gas, such as nitrogen or argon, prior to introduction of the reactants and maintaining a blanket of the gas in the reactor.
- the tetrakis(trihalosilyl)silane and the diisobutylaluminum hydride can be combined in any order.
- the diisobutylaluminum hydride is added to the solid tetrakis(trihalosilyl)silane.
- reverse addition i.e. addition of the tetrakis(trihalosilyl)silane to the diisobutylaluminum hydride is also possible.
- the tetrakis(trihalosilyl)silane is typically added to the diisobutylaluminum hydride as a solution in an organic solvent.
- the rate of addition of the diisobutylaluminum hydride to the tetrakis(trihalosilyl)silane (or vice- versa) is typically such that the temperature of the reaction mixture remains below the decomposition temperature of the tetrakis(trihalosilyl)silane.
- the tetrakis(trihalosilyl)silane is typically treated with the diisobutylaluminum hydride at a temperature of from -10 to 300 0 C, alternatively from 0 to 100 0 C, alternatively form 0 to 60 0 C, alternatively from 20 to 60 0 C.
- the reaction time depends on several factors, including the structures of the tetrakis(trihalosilyl)silane and the temperature.
- the reaction is typically carried out for an amount of time sufficient to complete reduction of the tetrakis(trihalosilyl)silane to the neopentasilane.
- the term "to complete reduction” means the silicon-bonded halogen atoms originally present in the tetraki(trihalolsilyl)silane are replaced with hydrogen atoms.
- the reaction time is typically from 0.1 to 4 h, alternatively from 0.5 to 2 h, alternatively 1 to 2 h, at a temperature of from 20 to 60 0 C.
- the mole ratio of the diisobutylaluminum hydride to the tetrakis(trihalosilyl)silane is typically from 12 to 16, alternatively from 12 to 14, alternatively from 13 to 14. When the mole ratio is less than 12, the mixture will contain unreacted tetrakis(trihalosilyl)silane in addition to neopentasilane. When the mole ratio is greater than 16, the cost of the process is increased unnecessarily.
- Step (iii) of the present method can be carried out either in the presence or absence of an organic solvent.
- the organic solvent can be any aprotic or dipolar aprotic organic solvent that does not react with the tetrakis(trihalosilyl)silane. the diisobutylaluminum hydride, or the neopentasilane product under the conditions of the present method. Examples of suitable solvents are as described and exemplified above for step (i) of the present method.
- the second mixture is distilled to remove the neopentasilane.
- the second reaction mixture can be distilled at atmospheric or subatmospheric pressure.
- the second reaction mixture is typically distilled under reduced pressure at a temperature not greater than 100 0 C.
- the term "reduced pressure,” means a pressure less than atmospheric pressure sufficient to volatilize the neopentasilane and remove it from the reaction mixture.
- the particular pressure depends on the distillation temperature.
- the pressure can be from 13.3 mPa to 20 kPa at a temperature of from 0 to 100 0 C, alternatively from 133 mPa to 6.7 kPa at a temperature of from 5 to 80 0 C, alternatively from 1.33 to 133 Pa at a temperature of from 20 to 60 0 C.
- the pressure required for volatilization of neopentasilane decreases.
- Steps (iii) and (iv) of the present method can be carried out in sequential order or simultaneously.
- the tetrakis(trihalosilyl)silane can be treated with the diisobutylaluminum hydride followed by distillation of the reaction mixture to remove the neopentasilane.
- the tetrakis(trihalosilyi)silane can be treated with the diisobutylaluminum hydride with concomitant distillation of the reaction mixture to remove the neopentasilane as it is formed, thus minimizing the occurrence of unwanted side reactions that can diminish purity and yield.
- the neopentasilane obtained by the method of the present invention can be further purified by at least one more distillation.
- the neopentasilane is typically distilled at a temperature of less than 100° C under reduced pressure.
- the composition of the present invention contains neopentasilane in a state of high purity.
- the composition typically contains at least 93% (w/w) neopentasilane, not greater than 5% (w/w) of other silanes, and not greater than 2% (w/w) of hydrocarbons, based on the total weight of the composition.
- the method of the present invention produces neopentasilane having high purity in high yield.
- the neopentasilane can be readily and efficiently removed from the reaction mixture by distillation. This separation minimizes the occurrence of unwanted side reactions that diminish purity and yield. Also, the neopentasilane is free of solvent, which can be deleterious in certain applications, especially in the electronics field. Further, the method can be carried out economically with a stoichiometric amount or only slight excess of diisobutylaluminum hydride. Still further, the method can be scaled to a commercial manufacturing process. [0048]
- the neopentasilane of the present invention can be used as a precursor for the formation of silicon-containing films, such as silica, silicon carbide, and silicon nitride, by chemical or physical vapor deposition.
- Example 1 A solution of 0.23 g of l,4-diazabicyclo[2.2.2]octane in 2.5 mL of diethyl ether was added under dry nitrogen to 230 grams (0.86 mol) of hexachlorodisilane in a 250-mL two- neck round bottom flask, with stirring. The mixture was allowed to stand undisturbed overnight, during which time a precipitate formed. The mixture was heated at 60 0 C under a pressure of 1.3 Pa for 7 hours to give 118 g of tetrakis(trichlorosilyl)silane as a white powder.
- the condensate contained 0.81 g (54% w/w) of neopentasilane, 0.61 g (41% w/w) of diisopropylbenzene, and 0.07 g (5% w/w) of other silanes, as determined GC-MS and *H NMR.
- neopentasilane was placed in a 500-mL jacketed flask equipped with a thermocouple, magnetic stir bar, and 5 -stage Oldershaw distillation column, under dry nitrogen.
- the neopentasilane was distilled by heating the flask at 67° C under vacuum (-6.6 kPa). After 15 g of distillate was collected, the receiver was changed and continued distillation produced 158 g of high purity (97.1%) neopentasilane.
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Abstract
Description
Claims
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US12/440,299 US8147789B2 (en) | 2006-10-24 | 2007-08-29 | Composition comprising neopentasilane and method of preparing same |
KR1020097008553A KR101506136B1 (en) | 2006-10-24 | 2007-08-29 | Composition comprising neopentasilane and method of preparing same |
CN200780039179XA CN101528813B (en) | 2006-10-24 | 2007-08-29 | Composition comprising neopentasilane and method of preparing same |
EP07811642.3A EP2076558B8 (en) | 2006-10-24 | 2007-08-29 | Composition comprising neopentasilane and method of preparing same |
JP2009534570A JP5103480B2 (en) | 2006-10-24 | 2007-08-29 | Composition containing neopentasilane and method for producing the same |
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Publication number | Priority date | Publication date | Assignee | Title |
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WO2010043551A1 (en) * | 2008-10-17 | 2010-04-22 | Wacker Chemie Ag | Method for producing neopentasilanes |
WO2010149547A1 (en) * | 2009-06-25 | 2010-12-29 | Wacker Chemie Ag | Method for producing dodeca halogen neopentasilanes |
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US9040009B2 (en) | 2009-12-04 | 2015-05-26 | Spawnt Private S.à.r.1. | Kinetically stable chlorinated polysilanes and production thereof |
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US9617391B2 (en) | 2008-05-27 | 2017-04-11 | Nagarjuna Fertilizers And Chemicals Limited | Halogenated polysilane and thermal process for producing the same |
EP3041850B1 (en) | 2013-09-05 | 2017-11-15 | Dow Corning Corporation | 2,2,4,4- tetrasilylpentasilane and its compositions, methods and uses |
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US11117807B2 (en) * | 2017-06-23 | 2021-09-14 | Jiangsu Nata Opto-Electronic Materials Co. Ltd. | Method of making aluminum-free neopentasilane |
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Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004036631A2 (en) * | 2002-10-18 | 2004-04-29 | Applied Materials, Inc. | Silicon-containing layer deposition with silicon compounds |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0760792B2 (en) | 1984-05-16 | 1995-06-28 | キヤノン株式会社 | Method of forming deposited film |
JPS6191010A (en) | 1984-10-09 | 1986-05-09 | Canon Inc | Method of forming piles film |
JP3517934B2 (en) * | 1994-03-24 | 2004-04-12 | 昭和電工株式会社 | Method of forming silicon film |
EP0902030B1 (en) * | 1997-08-27 | 2002-10-02 | Dow Corning Corporation | Compounds containing tetradecachlorocyclohexasilane dianion |
JPH11260729A (en) * | 1998-01-08 | 1999-09-24 | Showa Denko Kk | Production of higher order silane |
JP4465961B2 (en) * | 2000-08-02 | 2010-05-26 | 三菱マテリアル株式会社 | Method for producing disilicon hexachloride |
WO2002080244A2 (en) | 2001-02-12 | 2002-10-10 | Asm America, Inc. | Improved process for deposition of semiconductor films |
CN100471991C (en) * | 2002-10-18 | 2009-03-25 | 应用材料有限公司 | Silicon-containing layer deposition with silicon compounds |
US20040152287A1 (en) * | 2003-01-31 | 2004-08-05 | Sherrill Adrian B. | Deposition of a silicon film |
-
2007
- 2007-08-29 KR KR1020097008553A patent/KR101506136B1/en active IP Right Grant
- 2007-08-29 JP JP2009534570A patent/JP5103480B2/en active Active
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Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004036631A2 (en) * | 2002-10-18 | 2004-04-29 | Applied Materials, Inc. | Silicon-containing layer deposition with silicon compounds |
Non-Patent Citations (2)
Title |
---|
J.C. STURM ET AL: "Chemical Vapor Deposition Epitaxy of Silicon-Carbon Alloys at High Rates and Low Temperatures using Neopentasilane", Princeton Institute of Science and Technology of Materials (PRISM) and Department of Electrical Engineering , Princeton University Princeton, NJ and Applied Materials, Santa Clara ,CA ., XP002464465, Retrieved from the Internet <URL:http://www.princeton.edu/~sturmlab/pdfs/publications/CP.249.pdf> [retrieved on 20080114] * |
K H CHUNG, J C STURM, E SANCHEZ ,K K SINGH AND S KUPPUARO: "The high growth rate of epitaxial silicon-carbon alloys by using chemical vapour deposition and neopentasilane", SEMICOND.SCI .TECHNOL. (2007), vol. 22, 7 December 2006 (2006-12-07), Princeton Institute of Science and Technology of Materials (PRISM) and Department of Electrical Engineering, Princeton University , Princeton NJ, Applied Materials Santa Clara, CA, pages 158 - 160, XP002464466 * |
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EP2076558B1 (en) | 2018-04-18 |
CN101528813A (en) | 2009-09-09 |
KR101506136B1 (en) | 2015-03-26 |
CN101528813B (en) | 2011-10-26 |
TWI412530B (en) | 2013-10-21 |
JP5103480B2 (en) | 2012-12-19 |
JP2010507559A (en) | 2010-03-11 |
KR20090079908A (en) | 2009-07-22 |
US8147789B2 (en) | 2012-04-03 |
EP2076558A1 (en) | 2009-07-08 |
TW200821322A (en) | 2008-05-16 |
EP2076558B8 (en) | 2018-08-01 |
US20100176338A1 (en) | 2010-07-15 |
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