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(12) Patent Application Publication (10) Pub. No.: US 2004/0122248A1 Shenai-Khatkhate Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2004/0122248A1 Shenai-Khatkhate Et Al US 2004.0122248A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2004/0122248A1 Shenai-Khatkhate et al. (43) Pub. Date: Jun. 24, 2004 (54) PREPARATION OF ORGANOMETAL Related U.S. Application Data COMPOUNDS (60) Provisional application No. 60/419,622, filed on Oct. (75) Inventors: Deodatta Vinayak Shenai-Khatkhate, 18, 2002. Provisional application No. 60/422,043, Danvers, MA (US); Ronald L. Dicarlo filed on Oct. 29, 2002. JR., Newfields, NH (US); Michael L. Timmons, Durham, NC (US) Publication Classification Correspondence Address: (51) Int. Cl. ................................................... C07F 5/02 EDWARDS & ANGELL, LLP (52) U.S. Cl. .................................................................. 556/7 P.O. Box 91.69 (57) ABSTRACT Boston, MA 02209 (US) A method of preparing organometal compounds that does (73) Assignee: Shipley Company, L.L.C., Marlbor not use oxygenated Solvents is provided. The compounds ough, MA (US) produced by Such method are particularly useful as precur Sor compounds for metalorganic chemical vapor deposition (21) Appl. No.: 10/675,394 processes used in the manufacture of electronic devices. Methods of depositing metal films using Such organometal (22) Filed: Sep. 30, 2003 compounds are also provided. US 2004/O122248 A1 Jun. 24, 2004 PREPARATION OF ORGANOMETAL gallium compound. Certain procedures have been developed COMPOUNDS in an effort to remove Such Zinc impurities, Such as by contacting the trialkyl gallium compound with a metallic BACKGROUND OF THE INVENTION gallium-containing melt. Such contact may be achieved by refluxing the trialkyl gallium in the presence of the melt. 0001. The present invention relates generally to the field This purification procedure adds greatly to the manufactur of organometallic compounds. In particular, this invention ing costs of the trialkyl gallium compounds, Such as reduced relates to the preparation of alkyl metal compounds which output and increased waste handling costs, and does not are Suitable for use as precursors for chemical vapor depo guarantee complete removal of the impurities. Sition. 0006 For certain applications, such small amount of 0002 Metal layers may be deposited on Surfaces, such as aluminum present in a trialkyl gallium compound is not non-conductive Surfaces, by a variety of means Such as problematic. However, where ultrapure gallium-containing chemical vapor deposition (“CVD”), physical vapor depo layers are required, e.g. in blue LEDs, aluminum contami sition (“PVD”), and other epitaxial techniques such as liquid nation can be a problem. For example, when Such trialkyl phase epitaxy (“LPE'), molecular beam epitaxy ("MBE”), gallium compounds are used to deposit a gallium nitride and chemical beam epitaxy (“CBE). Chemical vapor depo layer, the Small amount of aluminum present will precipitate Sition processes, Such as metalorganic chemical vapor depo onto the growing film in the form of aluminum nitride. sition (“MOCVD), deposit a metal layer by decomposing Conventionally, trialkyl gallium compounds produced by a organometallic precursor compounds at elevated tempera transalkylation reaction with a trialkyl aluminum compound tures, i.e. above room temperature, either at atmospheric are Subjected to numerous purification Steps, Such as mul preSSure or at reduced pressures. In conventional CVD tiple distillations, in order to attempt to remove as much of processes, Suitable precursor compounds must have a Suf the aluminum impurity as possible. Such numerous purifi ficient vapor pressure to allow them to be transported to the cation Steps greatly increase the manufacturing cost and do deposition chamber. Both Solid and liquid precursor com not completely remove the aluminum impurity. Also, the pounds are known. trialkyl aluminum Starting materials are pyrophoric which 0003) A wide variety of metals may be deposited using makes handling them difficult and also increases the manu such CVD or MOCVD processes. See, for example, String facturing costs. Such trialkyl aluminum Starting materials fellow, Organometallic Vapor Phase Epitaxy. Theory and also typically contain Silicon impurities which are difficult to Practice, Academic Press, 2" Edition, 1999, for an over remove and causes problems in compound semiconductor View of Such processes. For example, gallium is used in a applications. variety of metal films produced by epitaxial growth, par ticularly in the manufacture of electronic devices Such as 0007 Hupe et al., Mechanism of the Stereoselective Alkyl integrated circuits and light emitting diodes (“LEDs). Group Exchange between Alkylboranes and Alkylzinc Com Exemplary gallium containing metal films include gallium pounds, Organometallics, vol. 21pp. 2203-2207 (2002), arsenide (“GaAs), indium-gallium-arsenide (“InCaAs), disclose the theoretical reaction of certain trialkylboranes aluminum-gallium-arsenide ("AlGaAs), indium-gallium with certain alkyl metal compounds, Such as diisopropylz aluminum-phosphide ("InGaAlP), indium-gallium-arsenic inc. Reactions of trialkylboranes with metal compounds phosphide ("InGaASP”), and indium-gallium-arsenide/gal other than alkyl metal compounds are not disclosed. lium-arsenide/aluminum-gallium-arsenide (“InGaAS/GaAS/ 0008. There is a need for a alkyl metal compounds, that AlGaAs”). Gallium arsenide phosphide (“GaAsP”) is are leSS costly to manufacture and can be prepared without suitable for visible LEDs and fiber optic emitters/detectors. the use of highly pyrophoric Starting materials. There is an additional need for trialkyl gallium and trialkyl indium 0004 For semiconductor and electronic device applica compounds having reduced or eliminated aluminum, Zinc tions, these organometallic precursor compounds must be and Silicon impurities. highly pure and be substantially free of detectable levels of both metallic impurities, Such as Silicon and Zinc, as well as SUMMARY OF THE INVENTION oxygenated impurities. Oxygenated impurities are typically 0009. It has been found that certain organometal com present from the Solvents used to prepare Such organome pounds, Such as trialkyl gallium, can be prepared in high tallic compounds, and are also present from other adventi yield and in high purity Starting from triorgano boron tious Sources of moisture or oxygen. compounds. Such reactions are performed in ether-free 0005 Trialkyl gallium compounds are typically used as Solvents. The organometal compounds produced by this precursor compounds for the deposition of gallium. Such method are extremely pure and Substantially free of oxy trialkyl gallium compounds are conventionally prepared by genated impurities. a transalkylation method Such as by reacting a gallium 0010. The present invention provides a method of pre trihalide with a trialkyl aluminum. The trialkyl gallium paring organometal compounds including the Step of react compounds generally contain Small amounts of impurities ing a triorgano boron compound with a metal halide com Such as aluminum, Zinc and Silicon, which are difficult to pound, wherein the metal halide compound includes a metal remove despite extensive purification procedures. Zinc is a Selected from gallium, indium, aluminum, cadmium and p-type impurity and even a few parts per million may be Zinc. Also contemplated by the present invention is an detrimental in certain Semiconductor applications. Dialky organometal compound free of oxygenated impurities, 1zinc compounds, which are often present in trialkyl gallium wherein the organometal compound includes a metal compounds, can be very difficult to remove using conven Selected from gallium, indium, aluminum, cadmium and tional methods, Such as distillation, due to the close proX Zinc. Preferred metal halide compounds are the metal diha imity of their boiling points to the corresponding trialkyl lides and trihalides. US 2004/O122248 A1 Jun. 24, 2004 0.011) Also provided by the present invention is a method lide compounds, triaryl aluminum compounds, dialkyl Zinc of depositing a metal layer including the steps of: a) con compounds, alkyl Zinc halide compounds, dialkyl cadmium veying an organometal compound in the gaseous phase to a compounds, alkyl cadmium halide compounds and the like. deposition chamber containing the Substrate; b) decompos Preferably, Such reaction is performed in an organic Solvent ing the organometal compound in the deposition chamber; free from oxygen Substitution. Such organometal com and c) depositing a metal layer on the Substrate; wherein the pounds are Substantially free of oxygenated impurities and organometal compound is free of oxygenated impurities, preferably free of such impurities. By “substantially free of and wherein the metal is Selected from gallium, indium, oxygenated impurities” it is meant that the organic Solvent aluminum, cadmium and zinc. contains S50 ppm of oxygenated impurities. 0012. The present invention further provides a method for manufacturing an electronic device including the Step of 0017 Suitable metal halide compounds are any that can depositing a metal layer on an electronic device Substrate be reacted with the triorgano boron compounds according to comprising the Steps of: a) conveying an organometal com the present invention and include, without limitation, gal pound in the gaseous phase to a deposition chamber con lium halide compounds, indium halide compounds, cad taining the Substrate; b) decomposing the organometal com mium halide compounds, and Zinc halide compounds. AS pound in the deposition chamber; and c) depositing a metal used herein,
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