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Method of Applying Single-Source Molecular Organic Chemical Vapor Deposition Agents John G Iowa State University Patents Iowa State University Research Foundation, Inc. 11-7-1995 Method of applying single-source molecular organic chemical vapor deposition agents John G. Verkade Iowa State University, [email protected] Follow this and additional works at: http://lib.dr.iastate.edu/patents Part of the Chemistry Commons Recommended Citation Verkade, John G., "Method of applying single-source molecular organic chemical vapor deposition agents" (1995). Iowa State University Patents. 227. http://lib.dr.iastate.edu/patents/227 This Patent is brought to you for free and open access by the Iowa State University Research Foundation, Inc. at Iowa State University Digital Repository. It has been accepted for inclusion in Iowa State University Patents by an authorized administrator of Iowa State University Digital Repository. For more information, please contact [email protected]. Method of applying single-source molecular organic chemical vapor deposition agents Abstract Neutral single-source molecular organic precursors containing tetradentate tripodal chelating ligands are provided that are useful for the preparation of films chemical vapor deposition. These complexes can be generally represented by the formula ##STR1## wherein "M" is selected from the group consisting of a lanthanide, an actinide, a Group IIIA metal, a Group IIIA metalloid, a Group IVA metal, a Group IVA metalloid, a Group VA metal, a Group VA metalloid, a Group IIIB metal, a Group IVB metal, a Group VB metal, a Group VIB metal, a Group VIIB metal, and a Group VIIIB metal. The ligand "Z", when present (k=1), is selected from the group consisting of hydrogen, halide, and a group bonded to "M" through N, O, P, S, As, Si, or C. "E.sub.c " is N, P, or As, and m=0-1. When "E.sub.t " is N, P, or As, m=1. When "E.sub.t " is O, S, or Se, m=0. Each "R.sup.1 " is selected from the group consisting of hydrogen, (C.sub.1 -C.sub.20)alkyl, (C.sub.2 -C.sub.20)alkenyl, (C.sub.2 -C.sub.20)alkynyl, (C.sub.6 -C.sub.18)aryl, (C.sub.7 -C.sub.20)aralkyl, a (C.sub.5 .C.sub.18)heterocycle, and triorganosilyl. In --[C(R.sup. 2).sub.2 ].sub.n --, n=1-4, and each "R.sup.2 " is selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, aryl, aralkyl, and a heterocycle. Keywords Chemistry Disciplines Chemistry This patent is available at Iowa State University Digital Repository: http://lib.dr.iastate.edu/patents/227 lllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllllll US005464656A United States Patent [19] [11] Patent Number: 5,464,656 Verkade [45] Date of Patent: Nov. 7, 1995 [54] METHOD OF APPLYING SINGLE-SOURCE A. H. Cowley et al., “Organometallic Chemical Vapor MOLECULAR ORGANIC CHEMICAL Deposition of HI/V Compound Semiconductors with Novel VAPOR DEPOSITION AGENTS Organometallic Precursors”, J. Am. Chem. Soc, 110, 6248-6249 (1988). [75] Inventor: John G. Verkade, Ames, Iowa A. H. Cowley et al., “An Aluminaphosphacubane, a New Aluminum Phosphide Precursor”, Angew. Chem. Int. Ed. [73] Assignee: Iowa State University Research EngL, 29, 1409-1410 (1990). Foundation, Inc., Ames, Iowa A. H. Cowley et al., “Preparation of Indium Antimonide Using a Single-Source Precursor”, Chem. Mater, 2, [21] Appl. No.: 253,106 221-222 (1990). [22] Filed: Jun. 2, 1994 A. H. Cowley et al., “III/V Precursors with P-H or As-H Bonds. A Low-Temperature Route to Gallium Arsenide and Related US. Application Data Gallium Phosphide”, Organometallics, 10, 652-656 (1991). A. H. Cowley et al., “Isopropylphosphido and Arsenido [60] Division of Ser. No. 911,923, Jul. 10, 1992, Pat. No. Derivatives of Gallium and Indium. Isolation of 5,344,948, which is a continuation-in-part of Ser. No. 841, Gallium-Phosphorous and Indium-Phosphorous Dimers 589, Feb. 25, 1992, abandoned. and Trimers”, Organometallics, 10, 1635-1637 (1991). [51] Int. GL6 ................................................... .. C23C 16/18 C. C. Cummins et al., “Trigonal-Monopyramidal MIII Com [52] US. Cl. .................. .. 427/248.1; 427/250; 427/255.6 plexes of the Type [M(N3N)] (M=Ti, V, Cr, Mn, Fe; [58] Field of Search ............................ .. 427/2481, 255.6, N3N=[(tBuMe2Si) NCH2CH2]3N)”, Angew. Chem. Int. Ed. 427/250 EngL, 31, 1501-1503 (Dec. 1992). [56] References Cited (List continued on next page.) U.S. PATENT DOCUMENTS Primary Examiner-Shrive Beck Assistant Examiner—Bret Chen 3,994,740 11/1976 Morton .................................... .. 106/65 Attorney, Agent, or Firm—Schwegman, Lundberg & Woess 4,885,376 12/1989 Verkade . ner 5,051,533 9/1991 Verkade .................................. .. 564/13 OTHER PUBLICATIONS [57] ABSTRACT C. C. Amato et al., “Gas Phase Decomposition of an Neutral single-source molecular organic precursors contain Organometallic Chemical Vapor Deposition Precursor to ing tetradentate tripodal chelating ligands are provided that AlN: [Al(CH)3)2NH2]3”, Mat. Res. Soc. Symp. Proc., are useful for the preparation of ?lms chemical vapor 119-124 (1990). deposition. These complexes can be generally represented D. A. Atwood et al., “X-ray crystal structure of the dimeth~ by the formula ylgallium azide polymer and its use as a gallium nitride precursor”, J. Organomet. Chem., 394, C6-C8 (1990). D. C. Bradley, “Metallo-organic Compounds containing Metal-Nitrogen bonds. Part I. Some Dialkylamino-derivatives of Titanium and Zirconium”, J. Chem. Soc., 3857-3861 (1960). D. C. Bradley et al., “Novel Precursors for the Growth of III-V Semiconductors by MOVPE”, J. Cryst. Growth, 75, 101-106 (1986). T. A. Brooks et al., “Plasma-Enhanced Chemical Vapor Deposition of Silicon Nitride from l,l,3,3,5, wherein “M” is selected from the group consisting of a S-Hexamethylcyclotrisilazane and Ammonia”, Thin Solid lanthanide, an actinide, a Group IIIA metal, a Group IIIA Films, 153, 521-529 (1987). metalloid, a Group IVA metal, a Group IVA metalloid, a D. M.-T. Chan et al., “Trialkoxyniu‘idomolydbenum Com Group VA metal, a Group VA metalloid, a Group IIIB metal, pounds: (RO)3MoEN. Preparation, Structures (R=t—Bu a Group IVB metal, a Group VB metal, a Group VIB metal, and i-Pr), and Comparisons with a Tungsten Analogue a Group VIIB metal, and a Group VIIIB metal. The ligand (R=t—Bu)”, Inorg. Chem, 25, 4170-4174 (1986). “Z”, when present (k=1), is selected from the group con H. L. M. Chang eta1., “Preparation, Structure and Properties sisting of hydrogen, halide, and a group bonded to “M” of V0,, and TiO2 Thin Films by MOCVD”, Mat. Res. Soc. through N, O, P, S, As, Si, or C. “E” is N, P, or As, and Symp. Proc., 168, 343-348 (1990). m=0-1. When “E,” is N, P, or As, m=l. When “E,” is O, S, H. Cohen, “Mono-and trititanates of cyclic nitrilotriethylene or Se, rn=0. Each “R1” is selected from the group consisting triorganotin titanate (IV)”, J. Organometal. Chem, 9, of hydrogen, (C1—C2O)alkyl, (C2-C2O)alkenyl, 177-179 (1967). (C2—C2O)alkynyl, (C6—C18)aryl, (C7-C2O)aralkyl, a H. J. Cohen, “Cyclic Nitrilotriethylene Triorganosilyl Titan (C5 . C18)heterocycle, and triorganosilyl. In —[C(R2)2]n—, n:1-4, and each “R2” is selected from the group consisting ate (IV): ‘Mono-’, ‘Di-’ and ‘Trititanates”’, J. Organomet. of hydrogen, alkyl, alkenyl, alkynyl, aryl, aralkyl, and a Chem, 5, 413-419 (1966). heterocycle. F. A. Cotton et al., Advanced Inorganic Chemistry, 4th Ed.; Wiley-Interscience, New York; pp. 737, 751, 767, 986, 1010, and 1011 (1980). 18 Claims, No Drawings 5,464,656 Page 2 OTHER PUBLICATIONS J. 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EtOSi(Ph2PNCH2CH2)2(HNCH2CH2)N", Organometallics, S. B. Desu et al., “Structure, Composition, and Properties of 9, 1464-1470 (1990). MOCVD ZrO2 Thin Films”, Mat. Res. Soc. Symp. Proc., D. Gudat et al., “Azasilatrane Methanolysis Pathways: Ste ' 168, 349-356 (1990). D. D. Devore et al., “Complexes of (Arylimido)vanadi reoelectronic In?uences”, Organometallics, 9, 2172-2175 um(V). Synthetic, Structural, Spectroscopic, and Theoretical (1990). R. L. Harlow, “Dimer of (2, 2', Studies of V(Ntol)Cl3 and Derivatives”, J. Am. Chem. Soc, 2"-Nitrilotriethanolato)(2-propanolato)titanium(IV), 109, 7408-7416 (1987). [Ti2(C6H12NO3)2(C3H7O)2]”, Acta Cryst., C39, 1344-1346 S. Dou et al., “Crystal structure of 2,8,9-trioxa-5-aza-l (1983). bora=tricyclo[3.3.3.01'5] undecane-3-one”, Jiegou Hua D. E. Heaton et al., “Potential Sources of the Electronics xue, 2, 273-276 (1983); Chem. Abstn, 106, Abstract No. Materials GaP and AlAs. Synthesis and X-Ray Structures of 1297092, p. 671 (1987) (Abstract Only). 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