CN102372735A - 1,3,5-三乙基-2,4,6-三氢-2,4,6-三乙基氨基-1,3,5-三氮杂-2,4,6-三硅代环己烷的制备方法 - Google Patents
1,3,5-三乙基-2,4,6-三氢-2,4,6-三乙基氨基-1,3,5-三氮杂-2,4,6-三硅代环己烷的制备方法 Download PDFInfo
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- CN102372735A CN102372735A CN2011102199548A CN201110219954A CN102372735A CN 102372735 A CN102372735 A CN 102372735A CN 2011102199548 A CN2011102199548 A CN 2011102199548A CN 201110219954 A CN201110219954 A CN 201110219954A CN 102372735 A CN102372735 A CN 102372735A
- Authority
- CN
- China
- Prior art keywords
- triethyl
- triaza
- solvent
- preparation
- trihydrido
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- SXOJCTZZWWFDLZ-UHFFFAOYSA-N 2-N,4-N,6-N,1,3,5-hexaethyl-1,3,5,2,4,6-triazatrisilinane-2,4,6-triamine Chemical compound CCN[SiH]1N(CC)[SiH](NCC)N(CC)[SiH](NCC)N1CC SXOJCTZZWWFDLZ-UHFFFAOYSA-N 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 title description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000002904 solvent Substances 0.000 claims abstract description 10
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000005052 trichlorosilane Substances 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims description 9
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- 239000010703 silicon Substances 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 238000005229 chemical vapour deposition Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- 241001269238 Data Species 0.000 description 1
- PXBCPOWAVFMNQD-UHFFFAOYSA-N N-silylethanamine Chemical compound CCN[SiH3] PXBCPOWAVFMNQD-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000006353 environmental stress Effects 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- -1 octane-iso Chemical compound 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical group [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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 System
- C07F7/02—Silicon compounds
- C07F7/21—Cyclic compounds having at least one ring containing silicon, but no carbon in the ring
-
- 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 System
- C07F7/02—Silicon compounds
- C07F7/025—Silicon compounds without C-silicon linkages
-
- 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 System
- 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
Abstract
本发明涉及一种制备1，3，5-三乙基-2，4，6-三氢-2，4，6-三乙基氨基-1，3，5-三氮杂-2，4，6-三硅代环己烷的方法，其中三氯硅烷与乙胺在溶剂中反应。
Description
技术领域
本发明涉及一种制备1，3，5-三乙基-2，4，6-三氢-2，4，6-三乙基氨基-1，3，5-三氮杂-2，4，6-三硅代环己烷的方法。
背景技术
在半导体的制造中，由于现有的生产SiO、SiN、SiON和SiOC层的方法，人们在寻找反应性化合物，其或者能在CVD(化学气相沉积)法中被直接沉积，或者用在ALD(原子层沉积)法中，并且在随后的反应步骤中反应。
适用于这个目的的一类分子是氨基硅烷或者硅氮烷。除了单体化合物外，还研究了低聚硅烷。
1，3，5-三乙基-2，4，6-三氢-2，4，6-三乙基氨基-1，3，5-三氮杂-2，4，6-三硅代环己烷(下面简称为三硅氮烷)早在1962年就被Sergeeva等人提及(ZH.Obschei Khimii 1962，32，1987 ff)，并描述了它的一些性质，但是没有描述它的合成。
发明内容
本发明提供一种制备1，3，5-三乙基-2，4，6-三氢-2，4，6-三乙基氨基-1，3，5-三氮杂-2，4，6-三硅代环己烷的方法，其中三氯硅烷与乙胺在溶剂中反应。
具体实施方式
现在已经发现三氯硅烷与乙胺在溶剂中反应最初仅生成很少的预期的三(乙基氨基)硅烷((EtNH)3SiH)，而是优先形成三硅氮烷。
所述溶剂优选是优选C4-C15，更优选C5-C10，尤其优选C6-C8的脂肪烃，优选戊烷、己烷、庚烷、辛烷、异辛烷、壬烷、癸烷，特别优选异己烷。
根据本发明的方法优选在20℃以下的温度，优选在5℃以下的温度，更优选在-10℃以下至-50℃的温度下，和900-1100hPa的压力下进行。
优选将乙胺加入到反应器的气体空间中，并且优选计量加入使得反应器的内部温度不超过-10℃。
基于1摩尔的三氯硅烷，使用6-10mol的乙胺，更优选6.2-7mol的乙胺，和200-1500g的溶剂，更优选800-1000g的溶剂。
在反应结束时，优选将获得的悬浮液过滤并优选用溶剂洗涤，并且优选对所得溶液蒸馏，蒸馏条件是温度优选在320℃以下，更优选为100-150℃，以及压力优选为从900-1100hPa的标准压力至减压，更优选1mbar以下。
在本发明中，所有提到的份数和百分比，除非另有说明，都是基于重量。除非另有说明，操作压力为环境压力，即约900-1100hPa，以及除非另有说明，温度为室温，即约20℃或者在没有额外的加热或冷却的情况下在室温下混合反应物得到的温度。所有粘度数据均是基于25℃的温度。
实施例
在装有搅拌器、夹套盘管冷凝器、温度传感器和滴加管路的夹套容器中首先加入1410g异己烷。向其中加入244g三氯硅烷。随后，将溶液冷却到-40℃并向反应器的气体空间中加入550g乙胺。选择计量添加使得反应器的内部温度不超过-10℃。形成白色悬浮液，其逐渐升温至20℃。然后，将悬浮液过滤，对固体进一步用异己烷洗涤并将获得的溶液蒸馏。在约130℃和0.1mbar的压力下，得到包含纯度大于98％的三硅氮烷的馏分(通过气相色谱确定)。
Claims (3)
1.一种制备1，3，5-三乙基-2，4，6-三氢-2，4，6-三乙基氨基-1，3，5-三氮杂-2，4，6-三硅代环己烷的方法，其包括三氯硅烷与乙胺在溶剂中反应。
2.权利要求1的方法，其中所述溶剂为C5-C10脂肪烃。
3.权利要求1或2的方法，其中首先加入溶剂并加入三氯硅烷，然后将溶液冷却到-10℃至-50℃，并将乙胺加入到反应器的气体空间中，选择计量加入使得反应器的内部温度不超过-10℃。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102010030895.1 | 2010-07-02 | ||
| DE102010030895A DE102010030895A1 (de) | 2010-07-02 | 2010-07-02 | Herstellung von 1,3,5-Triethyl-2,4,6-Trihydrido-2,4,6-Triethylamino-1,3,5-Triaza-2,4,6-Trisila-Cyclohexan |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102372735A true CN102372735A (zh) | 2012-03-14 |
| CN102372735B CN102372735B (zh) | 2014-09-24 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201110219954.8A Active CN102372735B (zh) | 2010-07-02 | 2011-07-01 | 1,3,5-三乙基-2,4,6-三氢-2,4,6-三乙基氨基-1,3,5-三氮杂-2,4,6-三硅代环己烷的制备方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8686173B2 (zh) |
| EP (1) | EP2402352B1 (zh) |
| JP (1) | JP2012012396A (zh) |
| KR (1) | KR101299034B1 (zh) |
| CN (1) | CN102372735B (zh) |
| DE (1) | DE102010030895A1 (zh) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8994276B2 (en) * | 2006-03-28 | 2015-03-31 | Wireless Environment, Llc | Grid shifting system for a lighting circuit |
| US10030037B2 (en) | 2014-05-30 | 2018-07-24 | Dow Silicones Corporation | Diaminosilane compounds |
| US10030038B2 (en) | 2014-05-30 | 2018-07-24 | Dow Silicones Corporation | Monoaminosilane compounds |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4594330A (en) * | 1984-03-22 | 1986-06-10 | Mitsubishi Gas Chemical Company, Inc. | Fine amorphous powder and process for preparing fine powdery mixture of silicon nitride and silicon carbide |
| CN1780889A (zh) * | 2003-03-07 | 2006-05-31 | 亨凯尔公司 | 可固化涂料组合物 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3187030A (en) | 1960-12-01 | 1965-06-01 | Dow Corning | Polymerization of silazanes by selected catalysts |
| DE2218960A1 (de) | 1972-04-19 | 1973-11-08 | Bayer Ag | Formkoerper aus mogenen mischungen von siliciumcarbid und siliciumnitrid und verfahren zu ihrer erstellung |
| US4788309A (en) * | 1985-04-26 | 1988-11-29 | Sri International | Method of forming compounds having Si-N groups and resulting products |
| JPS60258190A (ja) * | 1984-06-06 | 1985-12-20 | Mitsubishi Gas Chem Co Inc | 新規なシクロトリシラザン |
-
2010
- 2010-07-02 DE DE102010030895A patent/DE102010030895A1/de not_active Withdrawn
-
2011
- 2011-06-30 KR KR1020110064371A patent/KR101299034B1/ko active IP Right Grant
- 2011-07-01 JP JP2011147365A patent/JP2012012396A/ja active Pending
- 2011-07-01 US US13/175,337 patent/US8686173B2/en active Active
- 2011-07-01 CN CN201110219954.8A patent/CN102372735B/zh active Active
- 2011-07-01 EP EP11172355A patent/EP2402352B1/de active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4594330A (en) * | 1984-03-22 | 1986-06-10 | Mitsubishi Gas Chemical Company, Inc. | Fine amorphous powder and process for preparing fine powdery mixture of silicon nitride and silicon carbide |
| CN1780889A (zh) * | 2003-03-07 | 2006-05-31 | 亨凯尔公司 | 可固化涂料组合物 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE102010030895A1 (de) | 2012-01-05 |
| CN102372735B (zh) | 2014-09-24 |
| EP2402352A1 (de) | 2012-01-04 |
| US20120004435A1 (en) | 2012-01-05 |
| JP2012012396A (ja) | 2012-01-19 |
| KR101299034B1 (ko) | 2013-08-27 |
| KR20120003383A (ko) | 2012-01-10 |
| EP2402352B1 (de) | 2013-03-27 |
| US8686173B2 (en) | 2014-04-01 |
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