Organic compounds -- part of the class 532-570 series – Organic compounds – Rare earth containing
Reexamination Certificate
2005-06-28
2008-10-21
Gonzalez, P. Nazario (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Rare earth containing
C556S032000, C556S034000, C556S035000, C427S252000
Reexamination Certificate
active
07439338
ABSTRACT:
The present invention provides metal-containing compounds that include at least one β-diketiminate ligand, and methods of making and using the same. In certain embodiments, the metal-containing compounds include at least one β-diketiminate ligand with at least one fluorine-containing organic group as a substituent. In other certain embodiments, the metal-containing compounds include at least one β-diketiminate ligand with at least one aliphatic group as a substituent selected to have greater degrees of freedom than the corresponding substituent in the β-diketiminate ligands of certain metal-containing compounds known in the art. The compounds can be used to deposit metal-containing layers using vapor deposition methods. Vapor deposition systems including the compounds are also provided. Sources for β-diketiminate ligands are also provided.
REFERENCES:
patent: 5256244 (1993-10-01), Ackerman
patent: 5972430 (1999-10-01), DiMeo, Jr. et al.
patent: 6225237 (2001-05-01), Vaartstra
patent: 6455717 (2002-09-01), Vaartstra
patent: 6682602 (2004-01-01), Vaartstra
patent: 6828256 (2004-12-01), Vaartstra
patent: 6939578 (2005-09-01), Bradley et al.
patent: 7020981 (2006-04-01), Shero et al.
patent: 2002/0187578 (2002-12-01), Hong
patent: 2003/0113480 (2003-06-01), Kil et al.
patent: 2004/0247905 (2004-12-01), Bradley et al.
patent: 2005/0003075 (2005-01-01), Bradley et al.
patent: 2005/0107283 (2005-05-01), Bradley et al.
patent: 2005/0158479 (2005-07-01), Bradley et al.
patent: 2005/0227007 (2005-10-01), Bradley et al.
patent: 2006/0292841 (2006-12-01), Quick
patent: 2006/0292873 (2006-12-01), Millward et al.
patent: 2007/0234962 (2007-10-01), Suzuki et al.
patent: 42 02 889 A 1 (1993-08-01), None
patent: 42 02 899 (1993-08-01), None
patent: WO 03/095701 (2003-11-01), None
patent: WO 2007/002672 (2007-01-01), None
patent: WO 2007/002673 (2007-01-01), None
patent: WO 2007/002674 (2007-01-01), None
Hitchcock et al., Chemical Communications, Issue No. 10, pp. 1142-1143 (2003).
Barluenga et al., “Reaction of Fischer alkynylcarbene complexes with 1 -azadiene derivatives: unexpected formation of 3, 4-dihydropyridines,”New Journal of Chemistry, 2001; 25:8-10 (3 pgs). First published as an Advanced Article on the web Nov. 15, 2000.
Gusev et al., “Reaction of Methyldiacetylene with Primary Amines,”Bulletin of the Academy of Sciences of the USSR, Division Chemical Sciences(English Translation), 1974; 23:194-195 (2 pgs).
Knorr et al., “Configurational stability and reduced1H-NMR shifts of (pseudo)tetrahedral nickel(II) bis-chelates of 1,3-diimines [1],”English language translation (19 pgs) ofChem. Ber., 1981; 114:2104-2115 in German (12 pgs).
Park et al., “Routes toN, N'—Unsymmetrically Substituted 1, 3-Diketimines,”Journal of Organic Chemistry, 2005; 70:2075-2081 (7 pgs). Published on Web Feb. 9, 2005.
Rische et al., “New Tungsten(VI) Guanidinato Complexes: Synthesis, Characterization, and Application in Metal-Organic Chemical Vapor Deposition of Tungsten Nitride Thin Films,”Chem. Mater., 2006; 18:6075-6082 (8 pgs). Published on the web Nov. 15, 2006.
Schroth et al., “Nucleophilic addition of amines to diacetylene and 1 amniobut-1-en-3-ine,” English language translation (4 pgs) ofZ. Chem., 1969; 9(3):110-111 (2 pgs).
U.S. Appl. No. 11/168,160, filed Jun. 28, 2005, Quick, Timothy.
U.S. Appl. No. 11/169,082, filed Jun. 28, 2005, Millward et al.
Bourget-Merle et al., “The Chemistry of β-Diketiminatometal Complexes,”Chem. Rev., 2002;102:3031-3065. Published on Web Aug. 24, 2002.
Chisholm et al., “Lactide polymerization by well-defined calcium coordination complexes: comparisons with related magnesium and zinc chemistry,”Chem Commun.(Camb.), Jan. 7, 2003; 1:48-49. First published as an Advance Article on the Web Dec. 5, 2002.
Clegg et al., “Alkaline Earth Diazapentadienyl Compounds: Structure of [Ba2{(C6H11)NC(Me)CHC(Me)-N(C6H11)}3{(SiMe3)2N}],”Angew. Chem. Int. Ed, 1998;37(6):796-797.
Cui et al., “Synthesis and Structure of a Monomeric Aluminum(I) Compound [{HC(CMeNAr)2}Al] (Ar=2,6iPr2C6H3): A Stable Aluminum Analogue of a Carbene,”Agnew Chem. Int. Ed., 2000;39(23): 4274-4276.
Eisenstein et al., “Mono-, Di-, and Trianionic β-Diketiminato Ligands: A Computational Study and the Synthesis and Structure of [(YbL)3(THF)], L=[{N(SiMe3)C(Ph)}2CH],”J Am Chem Soc., 2003;125:10790-10791. Publised on Web Aug. 15, 2003.
El-Kaderi et al., “Sandwich Complexes of the Heavier Alkaline Earth Metals Containing η5-β-Diketiminato Ligand Sets,”Organometallics, 2004;23: 4995-5002. Published on Web Sep. 14, 2004.
Franceschini et al., “Volatile β-Ketoiminato- and β-Diketiminato-Based Zirconium Complexes as Potential MOCVD Precursors,”Inorganic Chemistry, 2003;42(22): 7273-7282. Published on Web Oct. 2, 2003.
Harder, Sjoerd, “Homoleptic β-Diketiminato Complexes of the Alkaline-Earth Metals: Trends in the Series Mg, Ca, Sr, and Ba,”Organometallics, 2002;21:3782-3787. Published on Web Aug. 9, 2002.
Harder, Sjoerd, “Intramolecular C-H Activation in Alkaline-Earth Metal Complexes,”Angew Chem Int Ed, 2003;42:3430-3434.
Hardman et al., “Synthesis and characterization of the monomer Ga{(NDippCMe)2CH} (Dipp=C6H3Pri2-2,6): a low valent gallium(I) carbene analogue,”Chem. Comm., 2000:1991-1992. First published as an Advance Article on the Web Sep. 27, 2000.
Hawley G.G., “The Condensed Chemcial Dictionary,”10th Edition, 1981, Van Norstrand Reinhold Co., New York, 225-26.
Hill and Hitchcock, “Bis(Phosphinimino)methyl derivatives of Ca, Sr and Ba: facile access to heavier alkaline earth organometallic chemistry,”Chem Commun. (Camb.), 2003;14:1758-1759. First published as an Advance Article on the Web Jun. 18, 2003.
Hitchcock et al., “New reactions of β-diketiminatolanthanoid complexes: sterically induced self-deprotonation of β-diketiminato ligands,”Chem Commun., 2005:951-953. First Published as an Advance Article on the Web Jan. 6, 2005.
Holland et al., “Electronically Unsaturated Three-Coordinate Chloride and Methyl Complexes of Iron, Cobalt, and Nickel,”J Am. Chem. Soc., 2002;124:14416-14424. Published on the Web Nov. 8, 2002.
Li et al., “Synthesis and Characterization of Copper(I) Amidinates as Precursors for Atomic Layer Deposition (ALD) of Copper Metal,”Inorganic Chemistry, 2005;44: 1728-1735. Published on the Web Feb. 3, 2005.
Piers and Emslie, “Non-cyclopentadienyl ancillaries in organogroup 3 metal chemistry: a fine balance in ligand design,”Coordination Chemistry Reviews, 2002;233-234:131-155.
Shimokawa and Itoh, “The First β-Diketiminate-Ag(I) Complexes. Macrocyclic Dinulcear and Tetranuclear Ag(I)-Complexes and Linear Coordination Polymer Ag(I)-Complex,”Inorganic Chemistry, 2005;44: 3010-3012. Published on the Web Apr. 5, 2005.
Vehkamäki et al., “Growth of SrTiO3and BaTiO3Thin Films by Atomic Layer Deposition,”Electrochemical and Solid-State Letters, 1999;2(10): 504-506. Available electronically Aug. 5, 1999.
El-Kaderi et al., “Synthesis, Structure, and Ligand Redistribution Equilibria of Mixed Ligand Complexes of the Heavier Group 2 Elements Containing Pyrazolato and β-Diketiminato Ligands,”Eur. J. Inorg. Chem., 2005:2081-2088. (published online Jun. 1, 2005.
Ashton et al., “A Regioselective route to 3-Alkyl-l-aryl-lH-pyrazole-5-carboxylates: synthetic studies and structural assignments,”Journal of Heterocyclic Chemistry, Mar. 1993;30(2):307-311.
Coe et al., “Reactions of tetrafluoroethene oligomers. Part 9. Some reactions of perfluoro-(l-ethyl-l-methylpropyl)(s-butyl)ethanolide (an α-Lactone),”Journal of the Chemical Society, Perkin Transactions I, 1989;6:1097-1104.
El-Kaderi et al., “Complexes of the heavier alkaline earth metals con
Millward Dan
Quick Timothy A.
Gonzalez P. Nazario
Micro)n Technology, Inc.
Mueting Raasch & Gebhardt, P.A.
LandOfFree
Beta-diketiminate ligand sources and metal-containing... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Beta-diketiminate ligand sources and metal-containing..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Beta-diketiminate ligand sources and metal-containing... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-4019134