EP0348476A1 - Procede de fabrication de composes d'alkyles metalliques - Google Patents

Procede de fabrication de composes d'alkyles metalliques

Info

Publication number
EP0348476A1
EP0348476A1 EP89900811A EP89900811A EP0348476A1 EP 0348476 A1 EP0348476 A1 EP 0348476A1 EP 89900811 A EP89900811 A EP 89900811A EP 89900811 A EP89900811 A EP 89900811A EP 0348476 A1 EP0348476 A1 EP 0348476A1
Authority
EP
European Patent Office
Prior art keywords
formula
compounds
compound
iii
ether
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.)
Withdrawn
Application number
EP89900811A
Other languages
German (de)
English (en)
Inventor
Friedrich-Wilhelm Reier
Herbert Schumann
Peter Wolfram
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck Patent GmbH
Original Assignee
Merck Patent GmbH
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Merck Patent GmbH filed Critical Merck Patent GmbH
Publication of EP0348476A1 publication Critical patent/EP0348476A1/fr
Withdrawn legal-status Critical Current

Links

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
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • 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
    • C07F5/062—Al linked exclusively to C

Definitions

  • the invention relates to a process for the preparation of metal alkyl compounds of the formula I.
  • M In, Ga or Al and R c ⁇ _ ⁇ 0 alkyl, which can also be branched, cyclic or unsaturated, and C fi _-. «-Aryl mean.
  • the metal alkyl compounds of the formula I can be prepared in particularly high purity and with very good yields.
  • the organometallic gas phase epitaxy is an increasingly important method with the potential for a broader industrial application.
  • the required components must be provided in the form of high-purity metal alkyl compounds.
  • Triethyl compounds of indium, gallium and aluminum were and are mainly used in this technology; more recently, the corresponding trimethyl compounds have been used increasingly.
  • metal alkyl compounds available on the market fluctuate relatively strongly in their quality. This is especially true for indium sources.
  • the known processes for the production of such metal alkyl compounds are in principle all based on the reaction of corresponding metal halides with organometallic alkylating agents. This prior art can be seen, for example, from:
  • electrochemical display processes can also be considered.
  • the metal alkyl compounds to be prepared are process-related in the form of solvent adducts, especially of ether adducts.
  • Such adducts are practically unsuitable for use in epitaxial processes; they have to be freed of the chemically bound solvent beforehand.
  • the conversion into ether-free metal alkyl compounds is usually carried out thermally, for example by vigorous heating with the aid of a vacuum if necessary. Because of the easy decomposability of the products, these treatments have a considerable potential for danger.
  • the object of the invention was therefore to find a method by which the trialkyl compounds of the
  • Metals indium, gallium and aluminum can be produced in high purity, which is suitable for epi-tax purposes. Above all, such a process should also be easy to handle and without safety problems and should provide good to very good product yields.
  • the invention also provides a process for the preparation of metal alkyl compounds of the formula I
  • M is In, Ga or Al, and R C, - ,,, - alkyl which may be branched, cyclic or ungesrelitig, and C 6 _ 10 aryl,
  • metal alkyl compounds of the formula I can be obtained in a particularly simple manner with a process of this type in a particularly high purity which is excellently suitable for epitaxy purposes and with a high yield.
  • the invention furthermore relates to the use of metal alkyl compounds produced by this process as source materials for the production of semiconductor layers, in particular by means of gas phase epitaxy.
  • R can be the same or different and for any alkyl radicals with 1-10 C atoms, which can also be branched, cyclic or unsaturated, or for aromatic radicals
  • 6-10 carbon atoms These can in particular be methyl, ethyl, n- or i-propyl, n-, sec-, i- or t-butyl as well as the isomeric forms of pentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclopropenyl, cyclobutenyl, cyclopentadienyl, cyclooctatetraenyl, l- Decen-3-ynyl, phenyl, tolyl, xylyl, or trimethylphenyl.
  • Particularly preferred compounds of the formula I are those in which R is methyl or ethyl.
  • the process according to the invention is based on the complex alkali metal or magnesium tetraalkyl metal compounds of the formulas II and III. These compounds have, as has been found, a particular advantage over the metal alkyl compounds of the formula I prepared in a conventional manner in that coordinatively bound solvents, such as ethers or ether-like solvents, contained in them due to the production process can very easily be removed virtually completely. This removal of bound ether or ether-like solvents is possible even at room temperature under vacuum. Gently heating up to about 100 ° C promotes removal. The ether can also be removed effectively by simply washing these compounds with inert organic solvents, if appropriate also in combination with vacuum drying.
  • coordinatively bound solvents such as ethers or ether-like solvents
  • Inert organic solvents are understood to mean those substances which do not contain any coordinating groups. These are primarily aliphatic solvents such as in particular pentane and hexane and aromatic solvents such as benzene, toluene, xylene or mesitylene.
  • the preferred procedure for the preparation of ether-free starting compounds of the formulas II and III is gentle heating in vacuo, washing with pentane or benzene and subsequent vacuum drying.
  • the starting compounds of the formulas II and III can be used for the process according to the invention by reacting corresponding metal trihalides or corresponding metal haloalkyl compounds with stoichiometric appropriate amounts of alkali metal compounds or dialkylmagnesium are produced.
  • Stoichiometrically corresponding means that the alkylating agents, based on the halogen content of the metal halo or metal haloalkyl compounds, are used in an excess of a stoichiometric equivalent, so that the alkali metal or magnesium tetraalkyl metal compounds of the formulas II and III form.
  • Preferred starting substances for this reaction are the trihalides of indium, gallium and aluminum, in particular their trichlorides, but also their alkyl dihalogen compounds or their dialkyl monohalogen compounds can be used advantageously.
  • Lithium alkyl compounds, in particular methyl lithium, are preferably used as the alkylating agent.
  • the reaction is normally carried out in an ether-like solvent, with normal atmospheric pressure and temperatures between room temperature and the boiling point of the solvent used being able to prevail.
  • Customary dialkyl ethers such as, in particular, diethyl ether, polyethers such as ethylene glycol dimethyl or diethyl ether or corresponding homologs and also cyclic ethers such as tetrahydrofuran or dioxane are used as solvents.
  • the ether-free alkali metal or magnesium tetraalkyl metal compounds of the formulas II or III are reacted with the stoichiometrically corresponding amount of a compound of the formula IV to give the desired product I.
  • the compounds of formula IV used are preferably the starting substances used in the preparation of the compounds of formulas II and III.
  • the trihalides, in particular the trichlorides of indium, gallium or aluminum, are again preferably used.
  • the stoichiometric amount of compound of the formula IV depends on its halogen content and on whether it is reacted with an alkali metal or magnesium tetraalkyl metal compound.
  • the resulting metal alkyl compounds of the formula I can be removed from the reaction mixture by distillation without problems.
  • the solvent is preferably first removed in vacuo and the end product is then distilled off from the remaining alkali metal or magnesium halide at atmospheric pressure. Fractional distillation enables the metal alkyl compounds of the formula I to be obtained in the highest purity which corresponds to today's requirements for epitaxy purposes.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Vapour Deposition (AREA)

Abstract

Un procédé permet d'obtenir de manière simple de très grandes quantités de composés d'alkyles métalliques ayant la formule (I): MR3, dans laquelle M représente In, Ga ou Ga Al et R représente C1-10-alkyle, qui peut être à chaîne ramifiée, cyclique ou insaturé, et C6-10-aryle, ces composés ayant un degré de pureté très élevé qui les rend propres à être utilisés en épitaxie.
EP89900811A 1987-12-11 1988-12-09 Procede de fabrication de composes d'alkyles metalliques Withdrawn EP0348476A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3742525 1987-12-11
DE3742525A DE3742525C2 (de) 1987-12-11 1987-12-11 Verfahren zur Herstellung von Metallalkylverbindungen und deren Verwendung

Publications (1)

Publication Number Publication Date
EP0348476A1 true EP0348476A1 (fr) 1990-01-03

Family

ID=6342671

Family Applications (1)

Application Number Title Priority Date Filing Date
EP89900811A Withdrawn EP0348476A1 (fr) 1987-12-11 1988-12-09 Procede de fabrication de composes d'alkyles metalliques

Country Status (4)

Country Link
EP (1) EP0348476A1 (fr)
JP (1) JP2887145B2 (fr)
DE (1) DE3742525C2 (fr)
WO (1) WO1989005303A1 (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK2198858T3 (da) 1998-03-26 2011-10-03 Astellas Pharma Inc Præparat med opretholdt frigivelse af en makrolidforbindelse såsom tacrolimus
US7063857B1 (en) 1999-04-30 2006-06-20 Sucampo Ag Use of macrolide compounds for the treatment of dry eye
JP6541657B2 (ja) * 2013-08-22 2019-07-10 ユミコア・アクチエンゲゼルシャフト・ウント・コムパニー・コマンディットゲゼルシャフトＵｍｉｃｏｒｅ ＡＧ ＆ Ｃｏ．ＫＧ アルキルインジウム化合物の製造方法及びその使用
DE102014109228A1 (de) 2014-07-01 2016-01-07 Umicore Ag & Co. Kg Verfahren zur Herstellung von Alkylindium-Verbindungen und deren Verwendung
EP3036243B1 (fr) * 2013-08-22 2019-10-09 Umicore AG & Co. KG Procédé de production de composés alkylindium et utilisation desdits composés
CN107106588B (zh) 2014-10-28 2020-08-11 山口晃史 用于改善妊娠状态的药剂及其使用
EP3056499B1 (fr) 2015-02-13 2018-04-18 Umicore AG & Co. KG Procédé de fabrication de composés alkylindium et leur utilisation
JP7465806B2 (ja) 2018-08-10 2024-04-11 晃史 山口 母体と胎児との関係における液性免疫関連疾患の治療薬
CN113226331A (zh) 2018-12-18 2021-08-06 山口晃史 用于改善不孕不育症或妊娠状态的药物

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1235106B (de) * 1960-02-29 1967-02-23 Union Carbide Corp Verfahren zur Gasplattierung von Aluminium auf erhitzte Gegenstaende
US4720560A (en) * 1984-10-25 1988-01-19 Morton Thiokol, Inc. Hybrid organometallic compounds, particularly for metal organic chemical vapor deposition

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO8905303A1 *

Also Published As

Publication number Publication date
WO1989005303A1 (fr) 1989-06-15
JP2887145B2 (ja) 1999-04-26
DE3742525C2 (de) 1998-02-19
JPH02502464A (ja) 1990-08-09
DE3742525A1 (de) 1989-06-22

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