JP6403192B2 - 高純度水素化シラン化合物の製造方法 - Google Patents
高純度水素化シラン化合物の製造方法 Download PDFInfo
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- JP6403192B2 JP6403192B2 JP2014181852A JP2014181852A JP6403192B2 JP 6403192 B2 JP6403192 B2 JP 6403192B2 JP 2014181852 A JP2014181852 A JP 2014181852A JP 2014181852 A JP2014181852 A JP 2014181852A JP 6403192 B2 JP6403192 B2 JP 6403192B2
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- Prior art keywords
- distillation
- silane compound
- distillation step
- hydrogenated silane
- formula
- Prior art date
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- -1 hydrogenated silane compound Chemical class 0.000 title claims description 91
- 238000004519 manufacturing process Methods 0.000 title claims description 24
- 238000004821 distillation Methods 0.000 claims description 161
- 229910052751 metal Inorganic materials 0.000 claims description 38
- 239000002184 metal Substances 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 27
- 239000010409 thin film Substances 0.000 claims description 20
- 239000012535 impurity Substances 0.000 claims description 15
- 238000009833 condensation Methods 0.000 claims description 12
- 230000005494 condensation Effects 0.000 claims description 12
- 238000000199 molecular distillation Methods 0.000 claims description 12
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 10
- 229910052708 sodium Inorganic materials 0.000 claims description 10
- 239000011734 sodium Substances 0.000 claims description 10
- 238000005292 vacuum distillation Methods 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052804 chromium Inorganic materials 0.000 claims description 5
- 239000011651 chromium Substances 0.000 claims description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 239000011591 potassium Substances 0.000 claims description 4
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 2
- GCOJIFYUTTYXOF-UHFFFAOYSA-N hexasilinane Chemical compound [SiH2]1[SiH2][SiH2][SiH2][SiH2][SiH2]1 GCOJIFYUTTYXOF-UHFFFAOYSA-N 0.000 description 56
- 229920000642 polymer Polymers 0.000 description 44
- 238000001704 evaporation Methods 0.000 description 26
- 230000008020 evaporation Effects 0.000 description 22
- 238000000746 purification Methods 0.000 description 17
- 239000002994 raw material Substances 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- 238000000526 short-path distillation Methods 0.000 description 6
- 150000004756 silanes Chemical class 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 239000004065 semiconductor Substances 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229910001873 dinitrogen Inorganic materials 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- 229910052719 titanium Inorganic materials 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 3
- 239000005052 trichlorosilane Substances 0.000 description 3
- YPCPIZLINSUBKP-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6-dodecachlorohexasilinane Chemical compound Cl[Si]1(Cl)[Si](Cl)(Cl)[Si](Cl)(Cl)[Si](Cl)(Cl)[Si](Cl)(Cl)[Si]1(Cl)Cl YPCPIZLINSUBKP-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical group [Ar] XKRFYHLGVUSROY-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
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000004759 cyclic silanes Chemical class 0.000 description 2
- OSXYHAQZDCICNX-UHFFFAOYSA-N dichloro(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](Cl)(Cl)C1=CC=CC=C1 OSXYHAQZDCICNX-UHFFFAOYSA-N 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 238000001095 inductively coupled plasma mass spectrometry Methods 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 235000002597 Solanum melongena Nutrition 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- LUXIMSHPDKSEDK-UHFFFAOYSA-N bis(disilanyl)silane Chemical compound [SiH3][SiH2][SiH2][SiH2][SiH3] LUXIMSHPDKSEDK-UHFFFAOYSA-N 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- LICVGLCXGGVLPA-UHFFFAOYSA-N disilanyl(disilanylsilyl)silane Chemical compound [SiH3][SiH2][SiH2][SiH2][SiH2][SiH3] LICVGLCXGGVLPA-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- SKTCDJAMAYNROS-UHFFFAOYSA-N methoxycyclopentane Chemical compound COC1CCCC1 SKTCDJAMAYNROS-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- CVLHDNLPWKYNNR-UHFFFAOYSA-N pentasilolane Chemical compound [SiH2]1[SiH2][SiH2][SiH2][SiH2]1 CVLHDNLPWKYNNR-UHFFFAOYSA-N 0.000 description 1
- DOBUHXUCKMAKSP-UHFFFAOYSA-N pentasilolanylsilane Chemical compound [SiH3][SiH]1[SiH2][SiH2][SiH2][SiH2]1 DOBUHXUCKMAKSP-UHFFFAOYSA-N 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- PLUQSKKKNPNZCQ-UHFFFAOYSA-N tetrasiletane Chemical compound [SiH2]1[SiH2][SiH2][SiH2]1 PLUQSKKKNPNZCQ-UHFFFAOYSA-N 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- VEDJZFSRVVQBIL-UHFFFAOYSA-N trisilane Chemical compound [SiH3][SiH2][SiH3] VEDJZFSRVVQBIL-UHFFFAOYSA-N 0.000 description 1
- SZMYSIGYADXAEQ-UHFFFAOYSA-N trisilirane Chemical compound [SiH2]1[SiH2][SiH2]1 SZMYSIGYADXAEQ-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2014181852A JP6403192B2 (ja) | 2013-09-06 | 2014-09-08 | 高純度水素化シラン化合物の製造方法 |
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| JP2013185100 | 2013-09-06 | ||
| JP2013185100 | 2013-09-06 | ||
| JP2014181852A JP6403192B2 (ja) | 2013-09-06 | 2014-09-08 | 高純度水素化シラン化合物の製造方法 |
Related Child Applications (1)
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| JP2018166232A Division JP6630415B2 (ja) | 2013-09-06 | 2018-09-05 | 高純度シクロヘキサシラン |
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| JP2015071530A JP2015071530A (ja) | 2015-04-16 |
| JP2015071530A5 JP2015071530A5 (enExample) | 2015-05-28 |
| JP6403192B2 true JP6403192B2 (ja) | 2018-10-10 |
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| JP2014181852A Active JP6403192B2 (ja) | 2013-09-06 | 2014-09-08 | 高純度水素化シラン化合物の製造方法 |
| JP2018166232A Active JP6630415B2 (ja) | 2013-09-06 | 2018-09-05 | 高純度シクロヘキサシラン |
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Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP7022512B2 (ja) * | 2017-03-09 | 2022-02-18 | 株式会社日本触媒 | ハロゲン元素含有量の少ないシクロヘキサシラン |
| TWI783027B (zh) * | 2017-08-28 | 2022-11-11 | 日商日本觸媒股份有限公司 | 氫化矽烷組合物 |
| JP7055674B2 (ja) * | 2018-03-15 | 2022-04-18 | 株式会社日本触媒 | ポリシラン組成物、及びヘテロ元素導入ポリシラン組成物の製造方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005120029A (ja) * | 2003-10-17 | 2005-05-12 | Jsr Corp | シラン化合物の精製方法 |
| KR101467412B1 (ko) * | 2006-10-06 | 2014-12-01 | 코비오 인코포레이티드 | 실리콘 폴리머, 실리콘 화합물 중합법 및 실리콘 폴리머 박막 형성법 |
| DE102010063823A1 (de) * | 2010-12-22 | 2012-06-28 | Evonik Degussa Gmbh | Verfahren zur Herstellung von Hydridosilanen |
| JP5808646B2 (ja) * | 2011-10-31 | 2015-11-10 | 株式会社日本触媒 | 環状シラン中間体の製造方法および環状水素化シランもしくは環状有機シランの製造方法 |
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- 2014-09-08 JP JP2014181852A patent/JP6403192B2/ja active Active
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Also Published As
| Publication number | Publication date |
|---|---|
| JP2015071530A (ja) | 2015-04-16 |
| JP2019001714A (ja) | 2019-01-10 |
| JP6630415B2 (ja) | 2020-01-15 |
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