KR100186947B1 - Process for the preparation of dimethylaluminium isopropoxide - Google Patents
Process for the preparation of dimethylaluminium isopropoxide Download PDFInfo
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- KR100186947B1 KR100186947B1 KR1019960028139A KR19960028139A KR100186947B1 KR 100186947 B1 KR100186947 B1 KR 100186947B1 KR 1019960028139 A KR1019960028139 A KR 1019960028139A KR 19960028139 A KR19960028139 A KR 19960028139A KR 100186947 B1 KR100186947 B1 KR 100186947B1
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- aluminum
- isopropyl acid
- room temperature
- vapor deposition
- dimethyl aluminum
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- 238000000034 method Methods 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title description 2
- HJYACKPVJCHPFH-UHFFFAOYSA-N dimethyl(propan-2-yloxy)alumane Chemical compound C[Al+]C.CC(C)[O-] HJYACKPVJCHPFH-UHFFFAOYSA-N 0.000 title 1
- 239000002253 acid Substances 0.000 claims abstract description 23
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 12
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 7
- 239000006227 byproduct Substances 0.000 abstract description 5
- 235000010210 aluminium Nutrition 0.000 description 10
- 238000005229 chemical vapour deposition Methods 0.000 description 10
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 125000005234 alkyl aluminium group Chemical group 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 238000000151 deposition Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- ORVACBDINATSAR-UHFFFAOYSA-N dimethylaluminum Chemical compound C[Al]C ORVACBDINATSAR-UHFFFAOYSA-N 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 230000008021 deposition Effects 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 238000000026 X-ray photoelectron spectrum Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000001182 laser chemical vapour deposition Methods 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 238000000623 plasma-assisted chemical vapour deposition Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/06—Aluminium compounds
- C07F5/061—Aluminium compounds with C-aluminium linkage
- C07F5/066—Aluminium compounds with C-aluminium linkage compounds with Al linked to an element other than Al, C, H or halogen (this includes Al-cyanide 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/06—Aluminium compounds
- C07F5/061—Aluminium compounds with C-aluminium linkage
- C07F5/066—Aluminium compounds with C-aluminium linkage compounds with Al linked to an element other than Al, C, H or halogen (this includes Al-cyanide linkage)
- C07F5/068—Aluminium compounds with C-aluminium linkage compounds with Al linked to an element other than Al, C, H or halogen (this includes Al-cyanide linkage) preparation of alum(in)oxanes
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Chemical Vapour Deposition (AREA)
Abstract
본 발명은 트리메틸알루미늄과 이소프로필산알루미늄을 반응시켜 상온에서 부산물의 생성 없이 이소프로필산디메틸알루미늄을 제조하는 방법에 관한 것이다.The present invention relates to a method for producing dimethyl aluminum isopropyl acid without the production of by-products at room temperature by reacting trimethylaluminum and aluminum isopropyl acid.
Description
본 발명은 이소프로필산디메틸알루미늄의 제조 방법에 관한 것이다.The present invention relates to a method for producing dimethyl aluminum isopropyl acid.
이소프로필산디메틸알루미늄은 지난 30년 동안 이 화합물을 언급한 문헌이 수 편에 불과할 정도로 주목을 받지 못한 화합물이다. 그러나 최근에 이 화합물이 화학 증착에 의해 산화 알루미늄 막을 형성하기 위한 원료로 사용하기에 적합하다는 것이 알려졌다[김윤수·고원용·구수진, 대한민국 특허 출원 제 95-46455 호].Dimethyl aluminum isopropylate has not received much attention in the last 30 years, with only a few references to the compound. Recently, however, it has been known that this compound is suitable for use as a raw material for forming an aluminum oxide film by chemical vapor deposition (Kim Yoon-soo, Ko Won-yong, Su-jin Koo, Korean Patent Application No. 95-46455).
염화알루미늄 또는 알킬산 알루미늄을 사용하여 산화알루미늄 막을 화학 증착하는 방법은 잘 알려져 있다[CVD 핸드북, pp. 665-689, 일본 화학공학회 편집, 이시우 ·이전 공역, 반도출판사(1993)]. 염화알루미늄의 증기압 100℃에서 1Torr이고, 알킬산 알루미늄 중에서 증기압이 가장 높은 이소프로필산알루미늄은 증기압이 100℃에서 1.1Torr로서, 이들은 상온보다 높은 온도로 가열하여야만 기체 상태로 운반되어 화학 증착할 수 있다는 단점이 있다.Methods of chemical vapor deposition of aluminum oxide films using aluminum chloride or aluminum alkylates are well known [CVD handbook, pp. 665-689, Edited by the Japan Chemical Engineering Association, Lee Si-woo and Former Airspace, Semi-published Press (1993). Aluminum isopropyl acid with 1Torr vapor pressure of aluminum chloride at 100 ° C and the highest vapor pressure among aluminum alkylates has 1.1Torr of vapor pressure at 100 ° C, which can be transported in gaseous state to be chemically deposited only when heated to a temperature higher than room temperature. There are disadvantages.
또한 상온에서 액체이고 증기압이 높은 알킬알루미늄을 알루미늄의 원료로 사용하여 산화알루미늄 막을 화학 증착하는 방법들도 알려져 있는데, 여기에서는 별도의 산소 공급 물질을 필요로 한다. 예를 들면 산소의 원료로 CO2를사용하는 플라즈마 도움 화학 증착법[Earl R. Lory and Leonard J. Olmer, Low Temerature Deposition Method for High Quality Aluminum Oxide Films, U.S.P. 4,675,089]과 N2O를 사용하는 레이저 화학 증착법[Makoto Minakata and Yoshitaka Furukawa, ArF Excimer Laser Induced CVD of Aluminum Oxide Films, Journal of Electronic Materials, 15, 159(1986)]이 있다. 그러나 레이저 화상 증착법과 플라즈마 도움 화학 증착법에 사용되는 장치는 열화학 증착 장치보다 복잡할 뿐 아니라, 한 면 위에 놓인 기질 표면에서만 화학 증착이 일어나기 때문에 증착 장치 내부의 모든 공간에 놓인 기질 표면에서 화학 증착이 일어나는 열화학 증착법보다 대량 생산 면에서 불리하다. 또한 알킬알루미늄은 공기에 노출되면 발화하므로 안정성이 떨어진다는 문제도 있다.Also known are methods of chemical vapor deposition of aluminum oxide films using liquid aluminum and high vapor pressure alkyl aluminum at room temperature as a source of aluminum, which requires a separate oxygen supply material. For example, plasma chemistry using CO 2 as a source of oxygen (Earl R. Lory and Leonard J. Olmer, Low Temerature Deposition Method for High Quality Aluminum Oxide Films, USP 4,675,089) and N 2 O Deposition methods (Makoto Minakata and Yoshitaka Furukawa, ArF Excimer Laser Induced CVD of Aluminum Oxide Films, Journal of Electronic Materials, 15, 159 (1986)). However, the devices used for laser image deposition and plasma assisted chemical vapor deposition are not only more complex than thermochemical deposition, but because chemical vapor deposition occurs only on the substrate surface on one side, chemical vapor deposition occurs on the substrate surface in all spaces inside the deposition apparatus. It is disadvantageous in mass production than thermochemical vapor deposition. In addition, alkyl aluminum ignites when exposed to air, so there is also a problem that the stability is poor.
이에 반하여 하기 화학식 1의 알킬산디알킬알루미늄을 원료로 사용하면 별도의 산소 공급 물질을 사용하지 않고서 고온으로 가열할 필요 없이 상온에서도 용이하게 화학 증착에 의해 산화알루미늄 막을 형성할 수 있다 :On the contrary, by using dialkylaluminum alkylate of Formula 1 as a raw material, it is possible to easily form an aluminum oxide film by chemical vapor deposition at room temperature without the need for heating to a high temperature without using a separate oxygen supply material:
(화학식 1)(Formula 1)
R1 2AlOR2 R 1 2 AlOR 2
상기식에서 R1과 R2는 같거나 서로 다르며, 각각 C1-C10알킬이다. R in the above formulaOneAnd R2Are the same or different and each is COne-C10Alkyl.
또한, 알킬산디알킬알루미늄은 휘발성이 커서 알킬알루미늄처럼 상온에서 쉽게 기체 상태로 운반될수 있으며, 공기에 노출되어도 알킬알루미늄과는 달리 발화하지 않기 때문에 휘발성 액체인 알킬알루미늄보다 훨씬 더 안전하다는 장점이 있다. 알킬산디알킬알루미늄중에서 특히 이소프로필산디메틸알루미늄이 산화알루미늄 막을 화학 증착하기 위한 원료로서 바람직하다.In addition, dialkylaluminum alkylate has a high volatility and can be easily transported in a gaseous state at room temperature like alkylaluminum, and it is much safer than volatile liquid alkylaluminum because it does not ignite unlike alkylaluminum when exposed to air. Among the alkyl dialkyl aluminums, dimethyl aluminum isopropyl acid is particularly preferred as a raw material for chemical vapor deposition of aluminum oxide films.
이소프로필산디메틸알루미늄을 합성하는 기존의 방법으로는 트리메틸알루미늄과 이소프로판올을 반응시키는 방법이 알려져 있으며[Paul S. Coan, Kirsten Folting, John C. Huffman, and Kenneth G. Caulton, Organometallics, 8, 2724(1989)], 하기 화학식 2와 같다 :Conventional methods for synthesizing dimethyl aluminum isopropyl acid are known to react trimethylaluminum with isopropanol [Paul S. Coan, Kirsten Folting, John C. Huffman, and Kenneth G. Caulton, Organometallics, 8, 2724 ( 1989), as shown in Formula 2 below:
(화학식 2)(Formula 2)
(CH3)3Al ＋iPrOH → (CH3)2AlOiPr ＋ CH4 (CH 3 ) 3 Al + i PrOH → (CH 3 ) 2 AlO i Pr + CH 4
-78℃-78 ℃
상기 반응에서는 열이 많이 발생하기 때문에 반드시 0℃보다 훨씬 낮은 온도에서 트리메틸알루미늄과 이소프로판올을 혼합하여야 한다. 따라서 이소프로필산디메틸알루미늄을 대량으로 합성하려면 온도를 충분히 낮출 수 있는 특별한 냉각 장치가 필요하며, 부산물인 가연성의 메탄 기체를 방출하는 장치도 또한 필요하다.Since much heat is generated in the reaction, trimethylaluminum and isopropanol must be mixed at a temperature much lower than 0 ° C. Therefore, the synthesis of dimethyl aluminum isopropylate in large quantities requires a special cooling device capable of sufficiently lowering the temperature, and also a device for releasing combustible methane gas as a byproduct.
따라서 본 발명의 목적은 이소프로필산디메틸알루미늄을 가연성의 부산물을 생성하지 않고 상온에서도 용이하게 합성할 수 있는 방법을 제공하는 것이다.Accordingly, an object of the present invention is to provide a method for easily synthesizing dimethyl aluminum isopropyl acid even at room temperature without generating flammable by-products.
상기 목적을 달성하기 위하여 본 발명에서는 트리메틸알루미늄과 이소프로필산알루미늄을 반응시켜 이소프로필산디메틸알루미늄을 제조하는 방법을 제공한다.In order to achieve the above object, the present invention provides a method for preparing dimethyl aluminum isopropyl acid by reacting trimethylaluminum and aluminum isopropyl acid.
이하 본 발명에 대하여 보다 상세히 설명한다.Hereinafter, the present invention will be described in more detail.
본 발명의 이소프로필산알루미늄 제조 방법은 하기 화학식 3으로 나타낼 수 있다 :The method for producing aluminum isopropyl acid of the present invention may be represented by the following Chemical Formula 3:
[화학식 3][Formula 3]
2(CH3)3Al ＋ Al(OiPr)3→ 3(CH3)2AlOiPr2 (CH 3 ) 3 Al + Al (O i Pr) 3 → 3 (CH 3 ) 2 AlO i Pr
상 온Room temperature
본 발명의 방법에서 반응 물질로 사용되는 이소프로필산디메틸알루미늄은 시판되는 것을 사용할 수 있으며 공지의 방법으로 제조하여 사용할 수도 있다. 반응에 사용할 때는 감압 증류하여 정제한 후 사용하는 것이 바람직하다.Dimethyl aluminum isopropyl acid, which is used as a reactant in the method of the present invention, may be commercially available and may be prepared and used by a known method. When using for reaction, it is preferable to use, after distilling under reduced pressure and refine | purifying.
상기 화학식 1에서 볼수 있는 바와 같이 본 발명의 제조 방법으로는 이소프로판올 보다 100 배 이상, 그리고 이소프로필산알루미늄보다 10 배 이상 비싼 트리메틸알루미늄 1 당량으로부터 이소프로필산디메틸알루미늄 1.5당량을 얻을 수 있으므로, 공지되어 있는 방법보다 50% 더 경제적으로 이소프로필산디메틸알루미늄을 합성할 수 있다. 또한 이 반응은 부산물이 없고 공지된 반응에 비해 열이 훨씬 적게 발생하므로 이소프로필산디메틸알루미늄을 대량으로 생산할 경우에도 별도의 냉각 장치가 필요하지 않으며, 필요한 경우라도 물을 사용하여 충분한 효과를 얻을 수 있으므로 반응기의 설계가 훨씬 더 간단해진다.As can be seen in the formula 1, 1.5 equivalents of dimethyl aluminum isopropyl acid can be obtained from 1 equivalent of trimethylaluminum which is 100 times or more expensive than isopropanol and 10 times or more expensive than aluminum isopropyl acid. Dimethyl aluminum isopropylate can be synthesized 50% more economically than the conventional method. In addition, since this reaction is free of by-products and generates much less heat than known reactions, a large amount of dimethyl aluminum isopropylate is not required for the production of a large amount of cooling equipment. This makes the design of the reactor much simpler.
본 발명의 방법으로 제조한 이소프로필산디메틸알루미늄을 사용하여 산화알루미늄막을 형성하는 방법은 별도의 운반 기체를 사용하지 않고서 이소프로필산디메틸알루미늄을 상온에서 기화시켜 300-600 ℃ 로 가열한 기질, 예를 들면 Si(000) 기질 위에 화학 증착을 실시하는 것이다. 이소프로필산디메틸알루미늄의 기화는 내부 압력이 수 mbar 정도인 반응기 내에서 행할 수 있다.The method for forming an aluminum oxide film using dimethyl aluminum isopropyl acid prepared by the method of the present invention is a substrate heated to 300-600 ℃ by evaporating dimethyl aluminum isopropyl acid at room temperature without using a separate carrier gas, for example For example, chemical vapor deposition is performed on a Si (000) substrate. Vaporization of dimethyl aluminum isopropyl acid can be carried out in a reactor having an internal pressure of several mbar.
이하 실시예를 통하여 본 발명을 더욱 상세히 설명할 것이다.The present invention will be described in more detail with reference to the following examples.
단, 본 발명의 범위가 하기 실시예만으로 한정되는 것은 아니다.However, the scope of the present invention is not limited only to the following Examples.
(실시예) : 이소프로필산디메틸알루미늄의 제조Example: Preparation of Dimethyl Aluminum Isopropyl Acid
트리메틸알루미늄 5.99g(83.1mmol)에 감압 증류하여 정제한 이소프로필산알루미늄 8.49g(41.5mmol)을 넣고 8 시간 동안 교반하였다. 얻은 액체를 10Torr에서 감압 증류하여 68-72℃에서 끊는 투명한 액체 12.52g(108 mmol, 87%수율)를 얻었다. 이 액체의 벤젠-d6용액의1H NMR 스펙트럼에서는 δ -0.47[s, Al(CH3)2, 6H]과 0.99[d, OCH(CH3)2, 6H]와 3.84[heptet, OCH(CH3)2, 1H] 위치에 봉우리가 관찰되었다.8.49 g (41.5 mmol) of purified aluminum aluminum isopropyl acid was added to 5.99 g (83.1 mmol) of trimethylaluminum, followed by stirring for 8 hours. The resulting liquid was distilled under reduced pressure at 10 Torr to give 12.52 g (108 mmol, 87% yield) of a clear liquid which was broken at 68-72 ° C. The 1 H NMR spectrum of this liquid benzene-d 6 solution showed δ -0.47 [s, Al (CH 3 ) 2 , 6H] and 0.99 [d, OCH (CH 3 ) 2 , 6H] and 3.84 [heptet, OCH ( CH 3 ) 2 , 1H] peaks were observed.
(응용예) 이소프로필산디메틸알루미늄을 원료로 한 산화알루미늄 막의 화학 증착 상기 실시예에서 제조한 이소프로필산디메틸알루미늄 0.1g을 상온에서 기화시켜 350℃로 가열한 Si(100) 기질 위에 5시간 동안 화학 증착을 실시하였다. 증착된 막의 X선 광전자 스펙트럼에는 모든 시료의 표면에서 나타나는 소량의 탄소 외에 산소와 알루미늄에 의한 봉우리만이 관찰되었다.(Application Example) Chemical Vapor Deposition of Aluminum Oxide Film Made from Dimethyl Aluminum Isopropyl Acid For 5 hours on Si (100) substrate, 0.1 g of dimethyl aluminum isopropyl acid prepared in the above Example was evaporated at room temperature and heated to 350 ° C. Chemical vapor deposition was carried out. In the X-ray photoelectron spectrum of the deposited film, only peaks due to oxygen and aluminum were observed in addition to the small amount of carbon appearing on the surfaces of all samples.
본 발명의 제조 방법에 따르면 이소프로필산디메틸알루미늄을 상온에서 가연성의 부산물을 생성하지 않고 합성할 수 있다.According to the production method of the present invention, dimethyl aluminum isopropyl acid can be synthesized at room temperature without generating flammable by-products.
Claims (2)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019960028139A KR100186947B1 (en) | 1996-07-12 | 1996-07-12 | Process for the preparation of dimethylaluminium isopropoxide |
| PCT/KR1997/000102 WO1998002444A1 (en) | 1996-07-12 | 1997-06-04 | Process for the preparation of dialkylaluminum alkoxide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019960028139A KR100186947B1 (en) | 1996-07-12 | 1996-07-12 | Process for the preparation of dimethylaluminium isopropoxide |
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| Publication Number | Publication Date |
|---|---|
| KR980009269A KR980009269A (en) | 1998-04-30 |
| KR100186947B1 true KR100186947B1 (en) | 1999-05-15 |
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| KR1019960028139A KR100186947B1 (en) | 1996-07-12 | 1996-07-12 | Process for the preparation of dimethylaluminium isopropoxide |
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| WO (1) | WO1998002444A1 (en) |
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| WO1998016667A1 (en) * | 1996-10-16 | 1998-04-23 | The President And Fellows Of Harvard College | Chemical vapor deposition of aluminum oxide |
| KR102123996B1 (en) * | 2013-02-25 | 2020-06-17 | 삼성전자주식회사 | Aluminum precursor, method of forming a thin layer and method of forming a capacitor using the same |
| WO2023177696A1 (en) * | 2022-03-16 | 2023-09-21 | Entegris, Inc. | Process for preparing dialkyl aluminum alkoxides |
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| US4732993A (en) * | 1986-11-21 | 1988-03-22 | Stauffer Chemical Company | Fluoroalkoxyaluminum compounds and their use in polymerization processes |
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| WO1998002444A1 (en) | 1998-01-22 |
| KR980009269A (en) | 1998-04-30 |
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