Containing -c(=x)-, Wherein X Is Chalcogen Patents (Class 556/117)
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Patent number: 10896820Abstract: A method for depositing a ruthenium-containing film on a substrate by a cyclical deposition process is disclosed. The method may include: contacting the substrate with a first vapor phase reactant comprising a metalorganic precursor, the metalorganic precursor comprising a metal selected from the group consisting of a cobalt, nickel, tungsten, molybdenum, manganese, iron, and combinations thereof. The method may also include; contacting the substrate with a second vapor phase reactant comprising ruthenium tetroxide (RuO4); wherein the ruthenium-containing film comprises a ruthenium-metal alloy. Semiconductor device structures including ruthenium-metal alloys deposited by the methods of the disclosure are also disclosed.Type: GrantFiled: February 14, 2018Date of Patent: January 19, 2021Assignee: ASM IP Holding B.V.Inventor: Suvi Haukka
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Patent number: 8962876Abstract: A precursor for the deposition of a thin film by atomic layer deposition is provided. The compound has the formula MxLy where M is a metal and L is an amidrazone-derived ligand or an amidate-derived ligand. A process of forming a thin film using the precursors is also provided.Type: GrantFiled: May 17, 2010Date of Patent: February 24, 2015Assignee: Wayne State UniversityInventors: Charles H. Winter, Thomas Joseph Knisley, Panditha Koralalage Don Mahesh Chinthaka Karunarathne
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Publication number: 20140352855Abstract: The reaction product of a nitro aromatic and a metal hydroxyl nitrate is presented. Gas generating compositions containing the reaction product are also presented. Gas generators and vehicle occupant protection systems containing the reaction product are also presented.Type: ApplicationFiled: June 3, 2014Publication date: December 4, 2014Applicant: TK Holdings Inc.Inventors: Sudhakar R Ganta, Scott M. Rambow, Deborah L. Hordos
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Publication number: 20140303109Abstract: Water-soluble fluorinated analogs of natural curcumin, and particularly difluoro Knoevenagel condensates and Schiff bases, along with their corresponding copper (H) complexes have improved bioavailablity over curcumin. The fluorine-substituted analogs of curcumin are useful as chemopreventive and/or therapeutic agents against cancers and/or against the development of drug-resistant cancer. A preferred compound is (IE,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene{4(3,4 difluorobenzaldehyde)}-3,5-dione.Type: ApplicationFiled: March 25, 2011Publication date: October 9, 2014Inventors: Fazlul H. Sarkar, Subhash Padhye
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Patent number: 8729285Abstract: A copper complex compound represented by Formula (1) is disclosed. in the formula, groups represented by R is a substituent, n is an integer of from 1 to 5 and the total carbon number contained in (R)n is 14 or more. A toner for electrophotography containing the compound is also disclosed.Type: GrantFiled: March 3, 2011Date of Patent: May 20, 2014Assignee: Konica Minolta Business Technologies, Inc.Inventors: Koji Daifuku, Ryohei Iwamoto, Keiko Ishidai, Kimihiko Ookubo, Kaori Ono, Issei Nakahara
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Patent number: 8692010Abstract: Disclosed are synthesis methods to produce copper bis-ketoiminate and copper bis-ketiminate compounds.Type: GrantFiled: July 13, 2012Date of Patent: April 8, 2014Assignee: American Air Liquide, Inc.Inventors: Andrey V. Korolev, Venkateswara R. Pallem
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Publication number: 20140087409Abstract: Provided are near-infrared silver sulfide quantum dots, a preparation method thereof and a biological application thereof. The silver sulfide quantum dots have hydrophilic groups derived from a mercapto-containing hydrophilic reagent attached on the surface thereof, and the hydrophilic reagent is any one of mercaptoacetic acid, mercaptopropionic acid, cysteine, cysteamine, thioctic acid and ammonium mercaptoacetate or any combination thereof. The silver sulfide quantum dots have high fluorescence yield, good fluorescence stability, good biocompatibility and uniform sizes. The preparation method has moderate reaction conditions, simple operation, short production cycle, good reproducibility and is easy to control. The silver sulfide quantum dots can be used in the application of cellular imaging and biological tissue imaging.Type: ApplicationFiled: February 10, 2012Publication date: March 27, 2014Applicant: Suzhou Institute of Nano-Bionics, Shinese Academy of SciencesInventors: Qiangbin Wang, Yejun Zhang
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Publication number: 20130253213Abstract: Provided is a method for producing cyanoacetic acid in a hydrolysis reaction of a predetermined cyanoacetate in the presence of an acid catalyst. Further, are provided methods for producing a cyanoacetic acid derivative and a metal containing compound by using the produced cyanoacetic acid as a staring material. Herein, the method for producing cyanoacetic acid enables the content of a malonic acid byproduct generated in the hydrolysis reaction to be greatly lowered, allowing the produced cyanoacetic acid to be used as a starting material without any purification treatments. Those advantageous effects result in the great improvement in the purity and yields of the cyanoacetic acid derivative and the metal containing compound produced by said cyanoacetic acid. Accordingly, the above mentioned methods make it possible to produce cyanoacetic acid, the cyanoacetic acid derivative and the metal containing compound, as excellent in the productivity and economical efficiency.Type: ApplicationFiled: March 15, 2013Publication date: September 26, 2013Applicant: Konica Minolta Business Technologies, Inc.Inventors: Dai IKEMIZU, Ryohei IWAMOTO, Keiko ISHIDAI, Kimihiko OOKUBO
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Patent number: 8530559Abstract: Provided is a composite including copper nanoparticles or copper(I) oxide nanoparticles and a thioether-containing organic compound represented by X(OCH2CHR1)nOCH2CH(OH)CH2SZ [X represents an alkyl group; R1 represents a hydrogen atom or a methyl group; n represents an integer of 2 to 100; R1 is independent between repeating units and may be the same or different; and Z represents an alkyl group, an allyl group, an aryl group, an arylalkyl group, —R2—OH, —R2—NHR3, or —R2—(COR4)m (where R2 represents a saturated hydrocarbon group; R3 represents a hydrogen atom, an acyl group, an alkoxycarbonyl group, or a benzyloxycarbonyl group; R4 represents a hydroxy group, an alkyl group, or an alkoxy group; and m represents 1 to 3)].Type: GrantFiled: February 28, 2011Date of Patent: September 10, 2013Assignee: DIC CorporationInventors: Yoshiyuki Sano, Ren-Hua Jin, Kaori Kawamura, Masafumi Uota
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Patent number: 8475685Abstract: A particle includes: a metal; and a compound containing a hydrogen-bonding forming group, an absorption group different from the hydrogen-bonding forming group, and an aromatic ring, M representing the metal, A representing the absorption group, B representing the hydrogen-bonding forming group, a representing an integer of 0 or greater, b representing an integer of 0 or greater, c representing an integer of 1 or greater, R1 representing an aromatic ring (a planar ring up to a pi-electron number of 24) and a derivative of the aromatic ring, R2 through R5 representing a hydrogen atom, saturated hydrocarbon, unsaturated hydrocarbon, an ether bond, an ester bond, a cyano group, or derivatives of the substances and bonds, and the compound having a structure expressed by the following chemical formula.Type: GrantFiled: March 12, 2010Date of Patent: July 2, 2013Assignees: Kabushiki Kaisha Toshiba, Institute of National Colleges of Technology, JapanInventors: Ko Yamada, Kenji Todori, Shigeru Machida
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Publication number: 20130095320Abstract: Provided is a composite including copper nanoparticles or copper(I) oxide nanoparticles and a thioether-containing organic compound represented by X(OCH2CHR1)nOCH2CH(OH)CH2SZ [X represents an alkyl group; R1 represents a hydrogen atom or a methyl group; n represents an integer of 2 to 100; R1 is independent between repeating units and may be the same or different; and Z represents an alkyl group, an allyl group, an aryl group, an arylalkyl group, —R2—OH, —R2—NHR3, or —R2—(COR4)m (where R2 represents a saturated hydrocarbon group; R3 represents a hydrogen atom, an acyl group, an alkoxycarbonyl group, or a benzyloxycarbonyl group; R4 represents a hydroxy group, an alkyl group, or an alkoxy group; and m represents 1 to 3)].Type: ApplicationFiled: February 28, 2011Publication date: April 18, 2013Applicant: DIC CORPORATIONInventors: Yoshiyuki Sano, Ren-Hua Jin, Kaori Kawamura, Masafumi Uota
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Publication number: 20120302815Abstract: A composition used to develop a reagent for investigating Ubl-modifications in cellular functions and in the treatment of cancer is provided. The composition comprises gold nanoparticle (AuNP)-ligand conjugates that include at least two components: gold nanoparticles (AuNPs) and modified ubiquitin- or ubiquitin-like interacting motif (UIM or ULIM) mimetics. In one embodiment, the modified ULM mimetic is a modified SUMO interaction motif (SIM) mimetic. According to the embodiments described herein, the compound inhibits ubiquitin- or ubiquitin-like protein (Ubl)-mediated protein-protein interactions and sensitizes cells to ionizing radiation. The modified UIM and ULIM mimetics may be conjugated to the AuNP such that each AuNP is conjugated to a plurality of modified UIM or ULIM mimetics. The modified ULIM mimetics may be conjugated to the AuNP via a thiol group.Type: ApplicationFiled: February 21, 2012Publication date: November 29, 2012Inventors: Yuan Chen, David Horne, Yi-Jia Li, Yuelong Ma, Angela L. Perkins-Harki, Yang Su
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Publication number: 20120058270Abstract: A precursor for the deposition of a thin film by atomic layer deposition is provided. The compound has the formula MxLy where M is a metal and L is an amidrazone-derived ligand or an amidate-derived ligand. A process of forming a thin film using the precursors is also provided.Type: ApplicationFiled: May 17, 2010Publication date: March 8, 2012Applicant: WAYNE STATE UNIVERSITYInventors: Charles H. Winter, Thomas Joseph Knisley, Panditha Koralalage Don Mahesh Chinthaka Karunarathne
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Publication number: 20110235151Abstract: An electrochromic material including a metal-organic framework including a metal, and an organic compound including a functional group, wherein the organic compound forms a coordination complex with the metal.Type: ApplicationFiled: July 21, 2010Publication date: September 29, 2011Applicant: SAMSUNG ELECTRONICS CO., LTD.Inventors: Chang-Ho NOH, Seog-Jin JEON, Seung-Uk SON
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Publication number: 20110180968Abstract: A method for making a carbon nanotube metal composite includes the following steps. A number of carbon nanotubes is dispersed in a solvent to obtain a suspension. Metal powder is added into the suspension, and then the suspension agitated. The suspension containing the metal powder is allowed to stand for a while. The solvent is reduced to obtain a mixture of the number of carbon nanotubes and the metal powder.Type: ApplicationFiled: October 15, 2010Publication date: July 28, 2011Applicants: TSINGHUA UNIVERSITY, HON HAI PRECISION INDUSTRY CO., LTD.Inventors: CHUN-HUA HU, CHANG-HONG LIU, SHOU-SHAN FAN
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Publication number: 20110151117Abstract: There is provided organic metal complexes for forming a metal thin layer, ink including the same, and a method for forming a metal thin layer using the same: wherein the organic metal complexes for forming a metal thin layer include Ag, and a ligand represented by the specific general formula; the organic metal complexes have an excellent stability and solubility toward a solvent; and the ink for forming a metal thin layer comprising the organic metal complexes is easy to form a metal thin layer of, and could be applied on the substrate consisting of material having low thermal stability because the ink can be decomposed at a low temperature.Type: ApplicationFiled: July 14, 2010Publication date: June 23, 2011Applicant: SAMSUNG ELECTRO-MECHANICS CO., LTD.Inventors: Young Kwan Seo, Dong Hoon Kim, Kwi Jong Lee
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Publication number: 20100239219Abstract: A particle includes: a metal; and a compound containing a hydrogen-bonding forming group, an absorption group different from the hydrogen-bonding forming group, and an aromatic ring, M representing the metal, A representing the absorption group, B representing the hydrogen-bonding forming group, a representing an integer of 0 or greater, b representing an integer of 0 or greater, c representing an integer of 1 or greater, R1 representing an aromatic ring (a planar ring up to a pi-electron number of 24) and a derivative of the aromatic ring, R2 through R5 representing a hydrogen atom, saturated hydrocarbon, unsaturated hydrocarbon, an ether bond, an ester bond, a cyano group, or derivatives of the substances and bonds, and the compound having a structure expressed by the following chemical formula.Type: ApplicationFiled: March 12, 2010Publication date: September 23, 2010Applicants: KABUSHIKI KAISHA TOSHIBA, INSTITUTE OF NATIONAL COLLEGES OF TECHNOLOGYInventors: Ko Yamada, Kenji Todori, Shigeru Machida
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Patent number: 7141688Abstract: The present invention is directed to novel fluorinated dye stabilizers having both high quenching efficiency and solubility in halogenated solvents. These dye stabilizers have shown a significantly effect on improving the dye fastness in hostile photooxidation conditions.Type: GrantFiled: October 14, 2003Date of Patent: November 28, 2006Assignee: SiPix Imaging, Inc.Inventors: Kai-Chia Feng, Ying-Syi Li, Jin Yang, HongMei Zang, Haiyan Gu, Sundaravel P. Ananthavel, Rong-Chang Liang
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Patent number: 7008748Abstract: Thermally developable materials such as thermographic and photothermographic materials include a co-precipitate comprising first and second organic silver salts, the first organic silver salt comprising a silver salt of a nitrogen-containing heterocyclic compound containing an imino group, and the second organic silver salt comprising a silver salt of a mercaptotriazole. The first organic silver salt can be used in the imaging process as a source of reducible silver ions, and the second organic silver salt can be a source of a toning agent. The co-precipitate can be prepared using double-jet precipitation techniques to provide an aqueous dispersion that can be used in imaging formulations.Type: GrantFiled: September 7, 2004Date of Patent: March 7, 2006Assignee: Eastman Kodak CompanyInventors: Dirk J. Hasberg, Doreen C. Lynch, Kui Chen-Ho, Chaofeng Zou
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Patent number: 6992200Abstract: Copper-containing thin films can be industrially advantageously formed by chemical vapor deposition using as the copper source a divalent copper complex bearing ?-diketonato ligands having silyl ether linkage. A representative example of the divalent copper complex is represented by the formula (I): wherein Z is hydrogen or alkyl; X is a group represented by the formula (I—I), in which Ra is alkylene, and each of Rb, Rc and Rd is alkyl; and Y is an alkyl group or a group represented by the formula (I—I), in which Ra is alkylene, and each of Rb, Rc and Rd is alkyl.Type: GrantFiled: January 31, 2003Date of Patent: January 31, 2006Assignee: UBE Industries, Ltd.Inventors: Takumi Kadota, Chihiro Hasegawa, Kouhei Watanuki
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Patent number: 6919467Abstract: The present invention provides a catalyst precursor and catalyst system comprising the precursor, an embodiment of the precursor is selected from the following structures: wherein T is a bridging group; M is selected from Groups 3 to 7 atoms, and the Lanthanide series of atoms the Periodic Table of the Elements; Z is a coordination ligand; each L is a monovalent, bivalent, or trivalent anionic ligand; X and Y are each independently selected from nitrogen, oxygen, sulfur, and phosphorus; R is a non-bulky substituent that has relatively low steric hindrance with respect to X; and R? is a bulky substituent that is sterically hindering with respect to Y.Type: GrantFiled: December 18, 2001Date of Patent: July 19, 2005Assignee: Univation Technologies, LLCInventor: Rex Eugene Murray
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Patent number: 6764537Abstract: A method for chemical vapor deposition of copper metal thin film on a substrate includes heating a substrate onto which the copper metal thin film is to be deposited in a chemical vapor deposition chamber; vaporizing a precursor containing the copper metal, wherein the precursor is a compound of (&agr;-methylstyrene)Cu(I)(hfac), where hfac is hexafluoroacetylacetonate, and (hfac)Cu(I)L, where L is an alkene; introducing the vaporized precursor into the chemical vapor deposition chamber adjacent the heated substrate; and condensing the vaporized precursor onto the substrate thereby depositing copper metal onto the substrate. A copper metal precursor for use in the chemical vapor deposition of a copper metal thin film is a compound of (&agr;-methylstyrene)Cu(I)(hfac), where hfac is hexafluoroacetylacetonate, and (hfac)Cu(I)L, where L is an alkene taken from the group of alkenes consisting of 1-pentene, 1-hexene and trimethylvinylsilane.Type: GrantFiled: June 2, 2003Date of Patent: July 20, 2004Assignee: Sharp Laboratories of America, Inc.Inventors: Wei-Wei Zhuang, Lawrence J. Charneski, David R. Evans, Sheng Teng Hsu
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Publication number: 20040077714Abstract: Neutral alpha amino diacid complexes of trace minerals and their use for animal nutrition.Type: ApplicationFiled: October 16, 2002Publication date: April 22, 2004Applicant: Zinpro CorporationInventors: Mahmoud M. Abdel-Monem, Michael D. Anderson
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Patent number: 6710197Abstract: A compound capable of efficiently cutting off light in the near infrared region, copper (meth)acryloyloxyethyl phosphate coordination complex, is synthesized including reacting (meth)acryloyloxyethyl phosphate and copper acetate monohydrate in water.Type: GrantFiled: November 12, 2002Date of Patent: March 23, 2004Assignee: Chung-Shan Institute of Science and TechnologyInventors: Shean-Jeng Jong, Chong Ma
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Patent number: 6703498Abstract: Water-soluble metal ion affinity compounds and methods for using the same are provided. The subject compounds include an aspartate based metal chelating ligand bonded to a water-soluble polymeric substrate, where the ligand is complexed with a metal ion. In certain embodiments, the subject compounds further include a member of a signal producing system, e.g., a directly or an indirectly detectable label moiety. Also provided are water-insoluble supports having the subject compounds present on, e.g., immobilized on, at least one surface thereof. The subject compounds find use in a variety of different applications, including analyte detection and analyte purification applications.Type: GrantFiled: June 20, 2002Date of Patent: March 9, 2004Assignee: Clontech Laboratories, Inc.Inventor: Grigoriy S. Tchaga
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Publication number: 20040044073Abstract: A composition and process is disclosed for treating an acne infection with a composition of electrolytically generated silver citrate. The composition of electrolytically generated silver citrate may be applied topically to the acne infection in an aqueous solution or may be incorporated within a cosmetic product., The acne composition may be combined with a composition component such as a cosmetic, a lotion, an emulsion, a gel or a soap.Type: ApplicationFiled: August 31, 2002Publication date: March 4, 2004Applicant: Innovative Medical ServicesInventor: Andrew B. Arata
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Chemical vapor deposition systems including metal complexes with chelating O- and/or N-donor ligands
Patent number: 6682602Abstract: A method of forming a film on a substrate using one or more complexes containing one or more chelating O- and/or N-donor ligands. The complexes and methods are particularly suitable for the preparation of semiconductor structures using chemical vapor deposition techniques and systems.Type: GrantFiled: August 19, 2002Date of Patent: January 27, 2004Assignee: Micron Technology, Inc.Inventor: Brian A. Vaartstra -
Patent number: 6642401Abstract: A &bgr;-diketonatocopper(I) complex which contains as a ligand (L) an allene compound and is represented by formula (2) wherein, R6 and R7 may be the same or different and each represents linear or branched C1-4 alkyl, C1-4 alkoxy, or linear or branched C1-4 fluoroalkyl, R8 represents hydrogen or fluorine, and L represents the allene compound, and a process for producing the same. The complex is useful in forming a thin copper film by metal-organic vapor deposition (hereinafter abbreviated as MOCVD) method.Type: GrantFiled: August 8, 2002Date of Patent: November 4, 2003Assignee: Nissan Chemical Industries, Ltd.Inventors: Hisayuki Watanabe, Hideki Musashi, Yasuo Kawamura
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Patent number: 6613924Abstract: Organosilver complexes with &bgr;-diketonates and neutral coordinating ligands are useful as silver precursors in chemical vapor deposition processes. The &bgr;-diketonates include 1,1,1,5,5,5-hexafluoro-2,4-pentanedionate (hfac), acetylacetonate (acac), 2,2,6,6-tetramethyl-3,5-heptanedionate (tmhd), 1,1,1-trifluoro-2,4-pentanedionate, (tfac), 2,2,7-trimethyl-3,5-octanedionate (tmod), 1,1,1-trifluoro-5,5-dimethyl-2,4-pentanedionate (tfh) 1,1,1,2,2,3,3,7,7,8,8,9,9,9-tetradecafluoro-4,6-nonanedionate (tdf). Neutral coordinating ligands include triphenylphosphine, tributylphosphine, pyridine, tetramethylethanediamine (TMEDA) and tetramethylpropanediamine (TMPDA).Type: GrantFiled: November 23, 1999Date of Patent: September 2, 2003Assignee: Research Foundation of State of New YorkInventors: John T. Welch, Silvana C. Ngo, Kulbinder K. Banger
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Patent number: 6534666Abstract: This invention relates to an improvement in a purification process for producing those liquid copper based complexes of &bgr;-diketones and, particularly the monovalent copper complexes of &bgr;-diketones, which are suited for application by chemical vapor deposition in the electronics industry. In the basic process for preparing a copper based complex, a reactive copper compound is reacted with a fluorinated &bgr;-diketonate and an organo source such as an olefinic source or one having acetylenic unsaturation. Purification is effected by contacting reaction product with a double deionized deoxygenated water source and preferably an acid/water source. An aqueous layer and an organic layer are formed with the aqueous layer containing byproducts and the organic phase containing product.Type: GrantFiled: December 27, 2001Date of Patent: March 18, 2003Assignee: Air Products and Chemicals, Inc.Inventors: Robert Sam Zorich, James Richard Thurmond, David Allen Roberts
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Publication number: 20020143202Abstract: A method for chemical vapor deposition of copper metal thin film on a substrate includes heating a substrate onto which the copper metal thin film is to be deposited in a chemical vapor deposition chamber; vaporizing a precursor containing the copper metal, wherein the precursor is a compound of (&agr;-methylstyrene)Cu(I)(hfac), where hfac is hexafluoroacetylacetonate, and (hfac)Cu(I)L, where L is an alkene; introducing the vaporized precursor into the chemical vapor deposition chamber adjacent the heated substrate; and condensing the vaporized precursor onto the substrate thereby depositing copper metal onto the substrate. A copper metal precursor for use in the chemical vapor deposition of a copper metal thin film is a compound of (&agr;-methylstyrene)Cu(I)(hfac), where hfac is hexafluoroacetylacetonate, and (hfac)Cu(I)L, where L is an alkene taken from the group of alkenes consisting of 1-pentene, 1-hexene and trimethylvinylsilane.Type: ApplicationFiled: March 27, 2001Publication date: October 3, 2002Inventors: Wei-Wei Zhuang, Lawrence J. Charneski, David R. Evans, Sheng Teng Hsu
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Patent number: 6455717Abstract: A method of forming a film on a substrate using one or more complexes containing one or more chelating O- and/or N-donor ligands. The complexes and methods are particularly suitable for the preparation of semiconductor structures using chemical vapor deposition techniques and systems.Type: GrantFiled: August 28, 2000Date of Patent: September 24, 2002Assignee: Micron Technology, Inc.Inventor: Brian A. Vaartstra
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Patent number: 6429325Abstract: A material for chemical vapor deposition comprising a &bgr;-diketonatocopper (II) complex which is liquid at room temperature.Type: GrantFiled: December 6, 2000Date of Patent: August 6, 2002Assignee: Asahi Denka Kogyo Kabushiki KaishaInventors: Kazuhisa Onozawa, Toshiya Shingen
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Patent number: 6365746Abstract: This invention relates to an organomercapto Au(I) complex having the formula [(M—SOL)n—A—S—Au—S—A—(SOL—M)n]M wherein M is a cationic counterion; SOL is a solubilizing group: A is a substituted or unsubstituted divalent organic linking group; and n is 1 to 4 and wherein the compound is symmetrical. It further relates to a method of manufacturing an organomercapto Au(I) complex comprising reacting an Au (I) complex with an organomercapto ligand and isolating the resulting organomercapto Au(I) complex from the reaction mixture.Type: GrantFiled: December 27, 1999Date of Patent: April 2, 2002Assignee: Eastman Kodak CompanyInventors: Roger Lok, Weimar W. White, Brian P. Cleary
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Publication number: 20020010363Abstract: A method for the reduction in iodine content in a mixture, particularly in a mixture of carboxylic acids and/or carboxylic anhydrides with alkyl iodides and/or hydriodic acid, comprises contacting the organic medium in the vapor phase at elevated temperature with a metal salt dispersed on activated charcoal. The metal salt may be a carboxylate salt, a carbonate, an oxide, a hydroxide and any other salt, which may react with the organic medium to give a metal carboxylate salt. The metal may be a main group element, a lanthanide, an actinide, zinc and copper. This process converts alkyl iodide compounds converted to their corresponding carboxylate esters, while the iodine is bound in the purification mass as inorganic iodide.Type: ApplicationFiled: December 21, 2000Publication date: January 24, 2002Inventor: Niels C. Schiodt
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Patent number: 6281377Abstract: A method of forming a volatile copper precursor for chemical vapor deposition of copper metal thin film includes formation of a volatile liquid having a chemical formula of (n-R-m-cyclohexene)Cu(I)(hfac) or (n-R-m-cyclopentene)Cu(I)(hfac), where n,m=1-6, and where R is a alkyl, such as methyl and ethyl.Type: GrantFiled: February 11, 2000Date of Patent: August 28, 2001Assignee: Sharp Laboratories of America, Inc.Inventors: Wei-Wei Zhuang, Tue Nguyen, Lawrence J. Charneski, David R. Evans, Sheng Teng Hsu
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Patent number: 6102993Abstract: Copper precursor formulations, including a copper precursor with at least one of (a) water, (b) a water precursor and (c) a non-ligand organic hydrate, are useful in CVD processes, e.g., in liquid delivery chemical vapor deposition, for forming a copper-containing material on a substrate. The disclosed copper precursor formulations are particularly useful in the formation of copper layers in semiconductor integrated circuits, e.g., for metallization of interconnections in such semiconductor device structures.Type: GrantFiled: August 3, 1999Date of Patent: August 15, 2000Assignee: Advanced Technology Materials, Inc.Inventors: Gautam Bhandari, Thomas H. Baum, Chongying Xu
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Patent number: 6096913Abstract: In a process for the synthesis of a first metal-ligand complex, M.sup.+n (L.sup.-).sub.n, where n.gtoreq.1, from a metal compound precursor and a ligand precursor, where the metal of the metal compound precursor may during the synthesis change to a valence in excess of n; the improvement, to suppress formation of a second metal-ligand complex of the metal with a valence in excess of n, of adding the elemental form of the metal to the synthesis of the first metal-ligand complex.Type: GrantFiled: June 10, 1999Date of Patent: August 1, 2000Assignee: Air Products and Chemicals, Inc.Inventors: John Anthony Thomas Norman, Yoshihide Senzaki, David Allen Roberts
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Patent number: 6090963Abstract: A metal(hfac), alkene ligand precursor has been provided. The alkene ligand includes double bonded carbon atoms, with first and second bonds to the first carbon atom, and third and fourth bonds to the second carbon atom. The first, second, third, and fourth bonds are selected from a the group consisting of H, C.sub.1 to C.sub.8 alkyl, C.sub.1 to C.sub.8 haloalkyl, and C.sub.1 to C.sub.8 alkoxyl. As a general class, these precursors are capable of high metal deposition rates and high volatility, despite being stable in the liquid phase at low temperatures. Copper deposited with this precursor has low resistivity and high adhesive characteristics. A synthesis method has been provided which produces a high yield of the above-described alkene ligand class of metal precursors.Type: GrantFiled: March 30, 1999Date of Patent: July 18, 2000Assignee: Sharp Laboratories of America, Inc.Inventors: Wei-Wei Zhuang, Tue Nguyen, Robert Barrowcliff, David Russell Evans, Sheng Teng Hsu
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Patent number: 6090964Abstract: A liquid organocuprous compound of formula (I) of the present invention can be conveniently used in a low-temperature CVD process for the production of a contaminant-free copper film having good step-coverage and hole-filling properties: ##STR1## wherein: R.sup.1 represents a C.sub.3-8 cycloalkyl group, andR.sup.2 and R.sup.3 are each independently a perfluorinated C.sub.1-4 alkyl group.Type: GrantFiled: January 19, 1999Date of Patent: July 18, 2000Assignee: Postech FoundationInventors: Shi-Woo Rhee, Doo-Hwan Cho, Jai-Wook Park, Sang-Woo Kang
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Patent number: 6046364Abstract: A process for recovering a 1,1,1,5,5,5-hexafluoro-2,4-pentanedione ligand from a metal-ligand complex byproduct such as Cu.sup.+2 (1,1,1,5,5,5-hexafluoro-2,4-pentanedionate.sup.-1).sub.2, comprising: providing a copper-ligand complex byproduct of Cu.sup.+2 (1,1,1,5,5,5-hexafluoro-2,4-pentanedionate.sup.-1).sub.2 in a process stream; cooling and condensing the copper-ligand complex byproduct of Cu.sup.+2 (1,1,1,5,5,5-hexafluoro-2,4-pentanedionate.sup.-1).sub.2 to separate it from the process stream; contacting the copper-ligand complex byproduct of Cu.sup.+2 (1,1,1,5,5,5-hexafluoro-2,4-pentanedionate.sup.-1).sub.2 with a protonation agent, such as: sulfuric acid, hydrochloric acid, hydroiodic acid, hydrobromic acid, trifluoroacetic acid, trifluoromethanesulfonic acid, acid ion exchange resin, hydrogen sulfide, water vapor and mixtures thereof; and recovering 1,1,1,5,5,5-hexafluoro-2,4-pentanedione.Type: GrantFiled: December 7, 1998Date of Patent: April 4, 2000Assignee: Air Products and Chemicals, Inc.Inventors: John Anthony Thomas Norman, John Cameron Gordon, Yoshihide Senzaki
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Patent number: 6015918Abstract: A Cu(hfac) allyl-derived ligand precursor has been provided. The ligand includes group consisting of alkyl, phenyl, trialkylsilane, trialkoxylsilane, halodialkylsilane, dihaloalkylsilane, trihalosilane, triphenylsilane, alkoxyl, halogen, chloroformate, cynanide, cycloalkyl, cycloalkylamine, alkyl ether, isocyanate, and pentafluorobenzene. Examples of the allyl-derived ligand precursors have proved to be stable at room temperatures, and sufficiently volatile at higher temperatures. Copper deposited with this precursor has low resistivity and high adhesive characteristics. A synthesis method has been provided which produces a high yield of the above-described precursors, including a Cu(hfac)(allyltrimethylsilane) precursor.Type: GrantFiled: March 30, 1999Date of Patent: January 18, 2000Assignee: Sharp Laboratories of America, Inc.Inventors: Wei-Wei Zhuang, Tue Nguyen, Greg Michael Stecker, David Russell Evans, Sheng Teng Hsu
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Patent number: 5994571Abstract: A Cu(hfac) precursor with a substituted ethylene ligand has been provided. The substituted ethylene ligand includes bonds to molecules selected from the group consisting of C.sub.1 to C.sub.8 alkyl, C.sub.1 to C.sub.8 haloalkyl, H, and C.sub.1 to C.sub.8 alkoxyl. One variation, the 2-methyl-1-butene ligand precursor has proved to be stable at room temperature, and extremely volatile at higher temperatures. Copper deposited with this precursor has low resistivity and high adhesive characteristics. Because of the volatility, the deposition rate of copper deposited with this precursor is very high. A synthesis method has been provided which produces a high yield of the above-described precursor.Type: GrantFiled: December 18, 1998Date of Patent: November 30, 1999Assignee: Sharp Laboratories of America, Inc.Inventors: Wei-Wei Zhuang, Tue Nguyen, Lawrence J. Charneski, David Russell Evans, Sheng Teng Hsu
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Patent number: 5914097Abstract: The present invention relates to the preparation of amino-acyl-type and catecholamine-type compounds having multiple carboxylic acid functional groups. Paramagnetic metal (II) or (III) ion chelate complexes are formed using these compounds for use as intravenous contrast agents to produce enhanced contrast magnetic resonance images of the heart, liver, biliary tree or upper small intestine. The mono- and di-amino acids, their esters and amides, and catecholamine-like derivatives, of EDTA, DTPA, and the like are prepared. The paramagnetic metal (II) or (III) ion complexes are formed and produce T1-related contrast effects in MR images. The compounds and complexes also appear to have low toxicities and to be relatively rapidly and completely cleared from the tissue of a living mammal, e.g. a human being.Type: GrantFiled: June 6, 1995Date of Patent: June 22, 1999Assignee: Regents of the University of CaliforniaInventor: David L. White
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Patent number: 5880149Abstract: The invention relates to metal complexes used to bind proteins and enzymes.Type: GrantFiled: September 27, 1996Date of Patent: March 9, 1999Assignee: California Institute of TechnologyInventors: Mark W. Grinstaff, Harry B. Gray, Thomas J. Meade
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Patent number: 5859214Abstract: Compounds of general formula I ##STR1## wherein Z.sup.1, Z.sup.2, X, R.sup.2 and R.sup.3 are as herein defined, are valuable pharmaceutical agents. In particular, the compounds are useful as contrast agents in NMR diagnosis.Type: GrantFiled: April 15, 1994Date of Patent: January 12, 1999Assignee: Schering AktiengesellshaftInventors: Heinz Gries, Erich Klieger, Bernd Raduchel, Heribert Schmitt-Willich, Hanns-Joachim Weinmann, Hubert Vogler, Gabriele Schuhmann-Giampieri, Jurgen Conrad
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Patent number: 5854363Abstract: An (omega-alkenyl) (cyclopentacarbyl) metallocene compound is provided. Polymerization processes therewith are also provided.Type: GrantFiled: November 24, 1997Date of Patent: December 29, 1998Assignee: Phillips Petroleum CompanyInventors: Michael Jung, Helmut G. Alt, M. Bruce Welch
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Patent number: 5792793Abstract: The present invention relates to a complex formed by the coordination between a thiol group-containing compound and a silver ion; an antibacterial, antifungal, and antiviral agent containing the same as the active agent; and an antibacterial, antifungal, and antiviral composition containing the above agent and a vehicle or a carrier.The agent has a wide antibacterial and antifungal spectrum and an antiviral activity, is well compatible with various vehicles and carriers, sustains its activity for long, and has reduced peroral toxicity, skin irritation and mucosa irritation.Type: GrantFiled: May 6, 1996Date of Patent: August 11, 1998Assignees: Meiji Milk Products Co., Ltd., Toyo Ink Mfg. Co., Ltd.Inventors: Munehiro Oda, Hiroyuki Itoh, Tetsushi Sudo, Sadatoshi Sakuma, Kenji Nomiya, Yasunori Suzuki, Yukiyoshi Jonoshita, Akira Kikuchi, Yoshiko Takabatake
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Patent number: 5767301Abstract: A method is provided for applying chemical vapor deposition (CVD) copper (Cu) to integrated circuit substrates using a Cu(hfac)(ligand) precursor with a silylolefin ligand including combinations of C1-C8 alkyl groups with at least one C2-C8 alkyloxy group. The alkyloxy groups include, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, and aryloxy, while the alkyl groups include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, and aryl. The oxygen atoms of the alkyloxy groups, and the long carbon chains of both the alkyl and alkyloxy groups, increase the stability of the precursor by contributing electrons to the Cu(hfac) complex. The improved bond helps insure that the ligand separates from the (hfac)Cu complex at consistent temperatures when Cu is to be deposited. Combinations of alkyloxy and alkyl groups allow the molecular weight of the precursor to be manipulated so that the volatility of the precursor is adjustable for specific process scenarios.Type: GrantFiled: January 21, 1997Date of Patent: June 16, 1998Assignees: Sharp Microelectronics Technology, Inc., Sharp Kabushiki KaishaInventors: Yoshihide Senzaki, Masato Kobayashi, Lawrence J. Charneski, Tue Nguyen
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Patent number: 5688981Abstract: Silver chelating agent and surfactant that exhibits photosensitivity and antimicrobial activity. The silver can be chelated with ethylenediaminetriacetic acid (ED3A) or salts thereof, or preferably with N-acyl ED3A or salts thereof. Antimicrobial activity is exhibited even at very low silver levels.Type: GrantFiled: November 21, 1996Date of Patent: November 18, 1997Assignee: Hampshire Chemical Corp.Inventor: Arthur M. Nonomura