WO1991019028A1 - Elementorganische verbindungen zur verwendung im elektronischen bereich - Google Patents
Elementorganische verbindungen zur verwendung im elektronischen bereich Download PDFInfo
- Publication number
- WO1991019028A1 WO1991019028A1 PCT/DE1991/000471 DE9100471W WO9119028A1 WO 1991019028 A1 WO1991019028 A1 WO 1991019028A1 DE 9100471 W DE9100471 W DE 9100471W WO 9119028 A1 WO9119028 A1 WO 9119028A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- compounds
- formula
- deposition
- organic
- preparation
- 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.)
- Ceased
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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/90—Antimony compounds
- C07F9/902—Compounds without antimony-carbon linkages
-
- C—CHEMISTRY; METALLURGY
- C30—CRYSTAL GROWTH
- C30B—SINGLE-CRYSTAL GROWTH; UNIDIRECTIONAL SOLIDIFICATION OF EUTECTIC MATERIAL OR UNIDIRECTIONAL DEMIXING OF EUTECTOID MATERIAL; REFINING BY ZONE-MELTING OF MATERIAL; PRODUCTION OF A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; SINGLE CRYSTALS OR HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; AFTER-TREATMENT OF SINGLE CRYSTALS OR A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; APPARATUS THEREFOR
- C30B25/00—Single-crystal growth by chemical reaction of reactive gases, e.g. chemical vapour-deposition growth
- C30B25/02—Epitaxial-layer growth
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/224—Phosphorus triamides
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/66—Arsenic compounds
- C07F9/68—Arsenic compounds without As—C bonds
-
- C—CHEMISTRY; METALLURGY
- C30—CRYSTAL GROWTH
- C30B—SINGLE-CRYSTAL GROWTH; UNIDIRECTIONAL SOLIDIFICATION OF EUTECTIC MATERIAL OR UNIDIRECTIONAL DEMIXING OF EUTECTOID MATERIAL; REFINING BY ZONE-MELTING OF MATERIAL; PRODUCTION OF A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; SINGLE CRYSTALS OR HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; AFTER-TREATMENT OF SINGLE CRYSTALS OR A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; APPARATUS THEREFOR
- C30B29/00—Single crystals or homogeneous polycrystalline material with defined structure characterised by the material or by their shape
- C30B29/10—Inorganic compounds or compositions
- C30B29/40—AIIIBV compounds wherein A is B, Al, Ga, In or Tl and B is N, P, As, Sb or Bi
- C30B29/42—Gallium arsenide
Definitions
- the invention relates to the use of organophosphorus, arsenic and antimony compounds which
- gallium arsenide, indium phosphide or gallium phosphide can be used for the production of electrical, electronic, optical and optoelectronic switching elements, lasers and compound semiconductors, the deposition of these layers taking place from the gas phase.
- MOVCD metal organic chemical vapor deposition
- MOMBE metal organic molecular beam epitaxy method
- Photo-MOVP decomposition of the substances by UV radiation
- laser CVD laser chemical vapor deposition method
- MOMS metal organic magneton sputtering method
- arsine (AsH 3 ) and phosphine (PH 3 ) have mainly been used as V-er components for the vapor deposition. Both are gases; Arsin is extremely dangerous due to its very low MAK value and its stability against oxygen and water.
- the object of the present invention was to develop organic compounds of phosphorus, arsenic and antimony, both with regard to their Manufacturing as well as their use are more advantageous.
- organometallic compounds of III Main group of PSE, preferably trimethyl gallium and indium, to deposit films with very good surfaces (comparable to those with arsine). It is noteworthy here that adduct formation (R 3 III ⁇ - IVR 3 ) does not occur in the gas phase, as can be observed when using RVH 2 .
- the invention thus relates to the organophosphorus, arsenic and antimony compounds of the formula
- M phosphorus, arsenic or antimony
- R H, CH 3 , C 2 H 3 , C 2 H 5 , C 3 H 5 , C 3 H 7 , iC 3 H 7 ,
- R ' NH 2 , N (CH 3 ) 2 , N (C 2 H 5 ) 2 , N (C 3 H 7 ) 2 ,
- M preferably denotes phosphorus or arsenic m preferably denotes 2 or 3
- R ' is preferably NH 2 , N (CH 3 ) 2 or N (CF 3 ) 2
- the presence of one or more nitrogen M (P, As, Sb) bond (s) is essential for the use of the compounds of the formula I according to the invention. Due to their high reactivity, it is ensured that they can easily be split off thermally. Furthermore, the amino functions shield the central atom M sterically to such an extent that no III-sources of the formula R 3 III form adducts in the gas phase and thus, foreseeable events in the epitaxial process can be expected or observed.
- the compounds of the formula I are outstandingly suitable for MOCVD epitaxy (or MOVPE method), since they decompose at higher temperatures with the release of the central atom. They are also for the other methods of vapor deposition, such as. B. Photo MOVP, laser CVD, MOMS or MOMBE suitable.
- Acrylic and aryl groups are introduced using alkali metal organyls or Grignard compounds.
- the amino groups are introduced with secondary amine with elimination of hydrogen chloride or with alkali metal amides with elimination of sodium chloride at the central atom.
- the amino compounds of the formula I are used as starting compounds in the gas-phase deposition processes of element-organic compounds which are known per se.
- the reaction conditions can be analogous to those known from the literature and the
- Another variant of the method according to the invention consists in that, in addition to those according to the invention, during the deposition process elemental compounds of formula I adds dopants. These are primarily volatile organometallic compounds of iron, magnesium, zinc and chromium.
- the layers produced by the method according to the invention can be used for the production of electrical, optical, electronic and optoelectronic switching elements, compound semiconductors or lasers.
- Dimethylamine is introduced into 90 g (0.5 mol) of high-purity arsenic trichloride (7N) in 1 liter of pentane with vigorous stirring at - 15 ° C. After saturating the solution with dimethylamine (recognizable by the settling of the precipitate), the reaction mixture is brought to 35 ° C. By reintroducing dimethylamine one checks for completeness of the reaction. The solution is filtered through a special filter (pore size 1). The pentane is distilled off at normal pressure, and the product is then fractionated. Colorless tris (dimethylamino) arsine is obtained as a colorless liquid speed with kp 57 ° C / 13 Torr.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Crystallography & Structural Chemistry (AREA)
- Materials Engineering (AREA)
- Metallurgy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Inorganic Chemistry (AREA)
- Chemical Vapour Deposition (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Crystals, And After-Treatments Of Crystals (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019920700154A KR920702442A (ko) | 1990-06-05 | 1991-06-05 | 전자분야에 사용하기 위한 유기원소화합물 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4017966.4 | 1990-06-05 | ||
| DE4017966A DE4017966C2 (de) | 1990-06-05 | 1990-06-05 | Verwendung elementorganischer Verbindungen zur Abscheidung aus der Gasphase |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1991019028A1 true WO1991019028A1 (de) | 1991-12-12 |
Family
ID=6407803
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/DE1991/000471 Ceased WO1991019028A1 (de) | 1990-06-05 | 1991-06-05 | Elementorganische verbindungen zur verwendung im elektronischen bereich |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP0460598B1 (https=) |
| JP (1) | JPH05500372A (https=) |
| KR (1) | KR920702442A (https=) |
| DE (1) | DE4017966C2 (https=) |
| ES (1) | ES2068429T3 (https=) |
| GR (1) | GR3015256T3 (https=) |
| TW (1) | TW260804B (https=) |
| WO (1) | WO1991019028A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10699899B2 (en) | 2011-10-12 | 2020-06-30 | Asm International N.V. | Atomic layer deposition of antimony oxide films |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4214224A1 (de) * | 1992-04-30 | 1993-11-04 | Merck Patent Gmbh | Verwendung von elementorganischen verbindungen zur abscheidung des elementes auf substraten |
| MY112590A (en) * | 1994-09-02 | 2001-07-31 | Sec Dep For Defence Acting Through His Defence Evaluation And Research Agency United Kingdom | Semi-conductor devices and their production |
| JP6210828B2 (ja) * | 2013-10-04 | 2017-10-11 | 株式会社Adeka | 薄膜形成用原料、薄膜の製造方法 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1438745A (fr) * | 1964-07-10 | 1966-05-13 | Rohm & Haas | Procédé de fabrication de dimères et trimères d'acrylates |
| DE1287571B (de) * | 1966-02-21 | 1969-01-23 | Frhr Von Hirsch Hubert | Verfahren zur Herstellung von Enaminen |
| EP0296257A1 (en) * | 1987-06-22 | 1988-12-28 | American Cyanamid Company | Branched monoalkyl group V A compounds as MOCVD element sources |
| EP0337304A1 (de) * | 1988-04-13 | 1989-10-18 | Preussag Pure Metals GmbH | Verwendung von Mono oder Diphenylarsinen zur Herstellung von Schicten nach dem Gasphasenepitaxieverfahren |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0052979B1 (en) * | 1980-11-18 | 1985-09-18 | BRITISH TELECOMMUNICATIONS public limited company | Improvements in the manufacture of group iiib-vb compounds |
| GB2162862B (en) * | 1984-07-26 | 1988-10-19 | Japan Res Dev Corp | A method of growing a thin film single crystalline semiconductor |
| EP0204724B1 (en) * | 1984-11-20 | 1990-01-24 | Hughes Aircraft Company | Method for deposition of gallium arsenide from vapor phase gallium-arsenic complexes |
| EP0319121B1 (en) * | 1987-11-30 | 1992-03-04 | Daidousanso Co., Ltd. | Apparatus for producing semiconductors |
| DE3841643C2 (de) * | 1988-12-10 | 1999-07-01 | Merck Patent Gmbh | Metallorganische Verbindungen und deren Verwendung |
| DE3842161A1 (de) * | 1988-12-15 | 1990-06-28 | Preussag Pure Metals Gmbh | Hochreine alkyl- und arylphosphine fuer gasphasenepitaxie-prozesse |
-
1990
- 1990-06-05 DE DE4017966A patent/DE4017966C2/de not_active Expired - Fee Related
-
1991
- 1991-06-04 EP EP91109099A patent/EP0460598B1/de not_active Expired - Lifetime
- 1991-06-04 ES ES91109099T patent/ES2068429T3/es not_active Expired - Lifetime
- 1991-06-05 JP JP3509506A patent/JPH05500372A/ja active Pending
- 1991-06-05 KR KR1019920700154A patent/KR920702442A/ko not_active Withdrawn
- 1991-06-05 WO PCT/DE1991/000471 patent/WO1991019028A1/de not_active Ceased
- 1991-06-25 TW TW080104400A patent/TW260804B/zh active
-
1995
- 1995-03-02 GR GR950400294T patent/GR3015256T3/el unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1438745A (fr) * | 1964-07-10 | 1966-05-13 | Rohm & Haas | Procédé de fabrication de dimères et trimères d'acrylates |
| DE1287571B (de) * | 1966-02-21 | 1969-01-23 | Frhr Von Hirsch Hubert | Verfahren zur Herstellung von Enaminen |
| EP0296257A1 (en) * | 1987-06-22 | 1988-12-28 | American Cyanamid Company | Branched monoalkyl group V A compounds as MOCVD element sources |
| EP0337304A1 (de) * | 1988-04-13 | 1989-10-18 | Preussag Pure Metals GmbH | Verwendung von Mono oder Diphenylarsinen zur Herstellung von Schicten nach dem Gasphasenepitaxieverfahren |
Non-Patent Citations (6)
| Title |
|---|
| BULL. CHEM. SOC. JPN, Band 60, Nr. 4, 1987, The Chemical Society of Japan, (JP), F. ANDO et al.: "Insertion of ketene and diphenylketene to the pnictogen-heteroatom bonds", Seiten 1564-1566, siehe Seite 1564 * |
| CHEMICAL ABSTRACTS, Band 114, Nr. 16, 22. April 1991, Seite 714, Zusammenfassung Nr. 154141f, (Columbus, Ohio, US), M.H. ZIMMER et al.: "Trisdimethylaminoarsine as arsenic source for the LP-MOVPE of gallium arsenide", & J. CRYST. GROWTH 1991, 107(1-4), 348-9, siehe die ganze Zusammenfassung * |
| CHEMTRONICS, Band 4, Nr. 1, M{rz 1989, Butterworth & Co. (Publishers) Ltd, (Guildford, Surrey, GB), G.T. MUHR et al.: "Recent advances in the development of arsine substitutes for use in metal organic vapour phase epitaxy of GaAs", Seiten 26-30 * |
| INORGANICA CHIMICA ACTA, Band 115, Nr. 2, 15. Mai 1986, Elsevier Sequoia, (CH), J.G. STEVENS et al.: "Synthesis and 121Sb Mössbauer study of a number of organoantimony(III) compounds containing antimony-main group V element bonds", Seiten 197-201, siehe die Zusammenfassung; Seite 199 * |
| JOURNAL OF CRYSTAL GROWTH, Band 96, Nr. 4, August 1989, Elsevier Science Publishers B.V. (North-Holland Physics Publishing Division), (Amsterdam, NL), A.C. JONES et al.: "Growth of AlxGa1-xAs by MOVPE using a new alkylaluminium precursor", Seiten 769-773 * |
| JOURNAL OF ORGANOMETALLIC CHEMISTRY, Band 299, 1986, Elsevier Sequoia S.A., (Amsterdam, NL), H. SCHUMANN: "Synthese und spektroskopische Charakterisierung von Cyclopentadienyleisen-Komplexen met P-N-Liganden des Typs (C6H5)3-nP(NR2)n (n=0-3; R=CH3, C2H5)", Seiten 169-178, siehe Seite 170 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10699899B2 (en) | 2011-10-12 | 2020-06-30 | Asm International N.V. | Atomic layer deposition of antimony oxide films |
Also Published As
| Publication number | Publication date |
|---|---|
| DE4017966A1 (de) | 1991-12-12 |
| GR3015256T3 (en) | 1995-06-30 |
| EP0460598B1 (de) | 1995-03-01 |
| JPH05500372A (ja) | 1993-01-28 |
| KR920702442A (ko) | 1992-09-04 |
| ES2068429T3 (es) | 1995-04-16 |
| TW260804B (https=) | 1995-10-21 |
| DE4017966C2 (de) | 1996-05-30 |
| EP0460598A1 (de) | 1991-12-11 |
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