Aromatic Patents (Class 526/251)
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Patent number: 9413012Abstract: A binder for a rechargeable lithium battery includes a copolymer having a weight average molecular weight of about 10,000 to about 500,000 and including a repeating unit represented by Chemical Formula X and a repeating unit represented by Chemical Formula Y-1: The binder may be used in preparing an electrode for a rechargeable lithium battery and a rechargeable lithium battery including the electrode exhibits improved stability, rate capability, and cycle-life.Type: GrantFiled: January 10, 2014Date of Patent: August 9, 2016Assignee: Aekyung Chemical Co., Ltd.Inventors: Byung-Joo Chung, Eon-Mi Lee, Nam-Seon Kim, Yang-Soo Kim, Kwang-Sik Choi
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Patent number: 8871882Abstract: A method for the preparation of a fluoropolymer by means of emulsion polymerization of a reaction mixture in an aqueous medium is disclosed wherein the reaction mixture includes a fluoromonomer having the structure of wherein R1, R2, and R3 are each independently hydrogen atoms, alkyl groups, substituted alkyl groups, or halogens, wherein at least one of R1, R2, and R3 is a fluorine atom, and wherein R is each independently a substituent on the styrenic ring, n is an integer from 0 to 5 representing the number of the substituents on the styrenic ring; b) an emulsion stabilizer combination comprising: i) an anionic surfactant; and, ii) a cationic surfactant or a non-ionic surfactant; and, c) a free-radical initiator.Type: GrantFiled: February 14, 2012Date of Patent: October 28, 2014Assignee: Akron Polymer Systems, Inc.Inventors: Xiaoliang Zheng, Dong Zhang, Jiaokai Jing, Ted Calvin Germroth, Frank W. Harris, Thauming Kuo, Bin Wang, Douglas Stephens McWilliams
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Patent number: 8703383Abstract: A copolymer has formula: wherein R1-R5 are independently H, C1-6 alkyl, or C4-6 aryl, R6 is a fluorinated or non-fluorinated C5-30 acid decomposable group; each Ar is a monocyclic, polycyclic, or fused polycyclic C6-20 aryl group; each R7 and R8 is —OR11 or —C(CF3)2OR11 where each R11 is H, a fluorinated or non-fluorinated C5-30 acid decomposable group, or a combination; each R9 is independently F, a C1-10 alkyl, C1-10 fluoroalkyl, C1-10 alkoxy, or a C1-10 fluoroalkoxy group; R10 is a cation-bound C10-40 photoacid generator-containing group, mole fractions a, b, and d are 0 to 0.80, c is 0.01 to 0.80, e is 0 to 0.50 provided where a, b, and d are 0, e is greater than 0, the sum a+b+c+d+e is 1, l and m are integers of 1 to 4, and n is an integer of 0 to 5. A photoresist and coated substrate, each include the copolymer.Type: GrantFiled: November 17, 2011Date of Patent: April 22, 2014Assignee: Rohm and Haas Electronic Materials LLCInventors: James W. Thackeray, Emad Aqad, Su Jin Kang, Owendi Ongayi
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Publication number: 20140106979Abstract: Polymers having orthogonal reactive groups and solid supports comprising polymers immobilized thereto are provided. The polymers find utility in any number of applications including immobilizing analyte molecules to solid supports for high throughput assays.Type: ApplicationFiled: October 11, 2013Publication date: April 17, 2014Applicant: NVS Technologies, Inc.Inventors: Aldrich N. K. Lau, Robert G. Eason
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Patent number: 8470513Abstract: A radiation-sensitive resin composition includes a polymer that includes at least one repeating unit (i) selected from a repeating unit shown by a formula (1), (2), and (3); and a repeating unit (ii) shown by a formula (4). R1 represents a hydrogen atom or a methyl group. Each R2 independently represents one of a linear or branched alkyl group having 1 to 12 carbon atoms, a linear or branched alkoxy group having 1 to 12 carbon atoms, and an alicyclic hydrocarbon group having 3 to 25 carbon atoms. p is an integer from 0 to 3, and q is an integer from 1 to 3, and p+q?5. A chemically-amplified positive-tone resist film that is sensitive to extreme ultraviolet rays (EUV) can be formed using the radiation-sensitive resin composition.Type: GrantFiled: September 23, 2011Date of Patent: June 25, 2013Assignee: JSR CorporationInventors: Kota Nishino, Ken Maruyama, Daisuke Shimizu, Toshiyuki Kai
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Patent number: 8338555Abstract: Photopolymers are provided with composites and electronic devices including such photopolymers. Specifically, organic thin film transistors comprising a semiconductor layer, a polymeric layer in contact with the semiconductor layer, a gate electrode, a source electrode and a drain electrode are disclosed, wherein the semiconductor layer comprises an organic semiconductor compound, and the polymeric layer comprises a photocrosslinked product of a photopolymer.Type: GrantFiled: July 14, 2011Date of Patent: December 25, 2012Assignee: Polyera CorporationInventors: He Yan, Antonio Facchetti, Tobin J. Marks
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Patent number: 8333360Abstract: Disclosed herein are polymeric molds that can be used to make molded articles. The polymeric molds are made from cyclic olefin polymers that may be formed by ring opening metathesis polymerization (ROMP) of a polycyclic monomer having two or more reactive double bonds and a cyclic monomer comprising one reactive double bond. Fluorinated monomers may be used. The polymeric molds may be structured molds in that they have at least one microstructured feature having a dimension of less than about 2 mm, or less than about 500 um. The polymeric molds may also have a plurality of such microstructured features. Also disclosed herein are methods of making the polymeric molds, methods of making molded articles therefrom, and the molded articles.Type: GrantFiled: April 28, 2009Date of Patent: December 18, 2012Assignee: 3M Innovative Properties CompanyInventors: Joseph D. Rule, Kevin M. Lewandowski
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OPTICAL AND THERMAL ENERGY CROSS-LINKABLE INSULATING LAYER MATERIAL FOR ORGANIC THIN FILM TRANSISTOR
Publication number: 20120292626Abstract: The problem of the present invention is to provide an organic thin film transistor insulating layer material capable of producing an organic thin film transistor having a small absolute value of threshold voltage and small hysteresis. The means for solving the problem is an organic thin film transistor insulating layer material comprising a macromolecular compound (A) containing repeating units having a fluorine atom-containing group, repeating units having a photodimerizable group and repeating units having a first functional group that generates a second functional group which reacts with active hydrogen by the action of electromagnetic waves or heat, and an active hydrogen compound (B).Type: ApplicationFiled: November 10, 2010Publication date: November 22, 2012Applicant: SUMITOMO CHEMICAL COMPANY, LIMITEDInventor: Isao Yahagi -
Publication number: 20120235148Abstract: A problem of the present invention is to provide an organic thin film transistor insulating layer material which is capable of forming a cross-linked structure without conducting a treatment at higher temperature, and which enables an organic thin film transistor to have a small absolute value of threshold voltage (Vth) when it is used for the formation of a gate insulating layer. The means for solving the problem is an organic thin film transistor insulating layer material including a macromolecular compound that has a repeating unit having a group containing a fluorine atom and a repeating unit having a photodimerization-reactive group.Type: ApplicationFiled: September 15, 2010Publication date: September 20, 2012Applicant: SUMITOMO CHEMICAL COMPANY, LIMITEDInventor: Isao Yahagi
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Publication number: 20120177578Abstract: The present invention generally relates to compositions, methods, and systems comprising polymers that are fluorous-soluble and/or organize at interfaces between a fluorous phase and a non-fluorous phase. In some embodiments, emulsions or films are provided comprising a polymer. The polymers, emulsions, and films can be used in many applications, including for determining, treating, and/or imaging a condition and/or disease in a subject. The polymer may also be incorporated into various optoelectronic device such as photovoltaic cells, organic light-emitting diodes, organic field effect transistors, or the like. In some embodiments, the polymers comprise pi-conjugated backbones, and in some cases, are highly emissive.Type: ApplicationFiled: August 19, 2011Publication date: July 12, 2012Applicant: Massachusetts Institute of TechnologyInventors: Timothy M. Swager, Jeewoo Lim, Yohei Takeda
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Patent number: 8198386Abstract: A fluorine-containing elastomer composition assuring a low compression set and comprising a perfluoroelastomer (A) comprising (a) 18 to 33% by mole of a perfluoro(alkyl vinyl ether) unit, (b) 0.3 to 0.6% by mole of a monomer unit having at least one selected from the group consisting of a nitrile group, a carboxyl group and an alkoxycarbonyl group and (c) a tetrafluoroethylene unit.Type: GrantFiled: April 9, 2008Date of Patent: June 12, 2012Assignee: Daikin Industries, Ltd.Inventors: Tatsuya Morikawa, Hirokazu Komori, Meiten Koh
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Patent number: 8193276Abstract: A fluorocopolymer capable of exhibiting excellent water and oil resistance even with its perfluoroalkyl group being a short chain, and a water and oil proofing composition containing it, are provided. A water and oil proofing composition containing a fluorocopolymer (A) comprising from 40 to 98 mass % of polymerized units (a?) having a C1-6 perfluoroalkyl group, from 1 to 50 mass % of polymerized units (b?) having an alkylene oxide and from 1 to 10 mass % of polymerized units (c?) based on a monomer represented by CH2?C(COOH)-Q-COOH (wherein Q is a C1-4 alkylene group, etc.).Type: GrantFiled: January 28, 2010Date of Patent: June 5, 2012Assignee: Asahi Glass Company, LimitedInventors: Shuichiro Sugimoto, Takao Hirono, Eiji Morimoto
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Publication number: 20120056249Abstract: Embodiments in accordance with the present invention provide for the use of polycycloolefins in electronic devices and more specifically to the use of such polycycloolefins as interlayers applied to fluoropolymer layers used in the fabrication of electronic devices, the electronic devices that encompass such polycycloolefin interlayers and processes for preparing such polycycloolefin interlayers and electronic devices.Type: ApplicationFiled: September 1, 2011Publication date: March 8, 2012Applicants: Promerus LLC, Merck Patent GmbHInventors: David Christoph Mueller, Pawel Miskiewicz, Toby Cull, Piotr Wierzchowiec, Andrew Bell, Edmund Elce, Larry F. Rhodes, Kazuyoshi Fujita, Hendra Ng, Pramod Kandanarachchi, Steven Smith
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Patent number: 7981989Abstract: Photopolymer-based dielectric materials are provided with methods for preparing the same. Composites and electronic devices including such dielectric materials also are provided.Type: GrantFiled: November 28, 2007Date of Patent: July 19, 2011Assignee: Polyera CorporationInventors: He Yan, Antonio Facchetti, Tobin J. Marks
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Patent number: 7947791Abstract: The present invention provides a fluorinated polymer excellent in the crosslinking reactivity, crosslinked rubber physical properties and chemical resistance, and its crosslinked rubber. A fluorinated polymer comprising repeating units (a) based on at least one monomer selected from the group consisting of ethylenic unsaturated compounds each having a hydroxyphenyl group, repeating units (b) based on at least one fluoromonomer selected from the group consisting of tetrafluoroethylene, hexafluoropropylene, vinylidene fluoride, 3,3,3-trifluoropropene, 1,3,3,3-tetrafluoropropene, 1,1,2-trifluoroethylene, vinyl fluoride, 1,2-difluoroethylene and CF2?CF—O—Rf (wherein Rf is a C1-8 saturated perfluoroalkyl group or a perfluoro(alkoxyalkyl) group) and, if necessary, repeating units (c) based on at least one hydrocarbon monomer selected from the group consisting of ethylene, propylene and CH2?CH—O—R1.Type: GrantFiled: March 19, 2009Date of Patent: May 24, 2011Assignee: Asahi Glass Company, LimitedInventors: Jumpei Nomura, Toshikazu Yoneda, Mitsuru Seki, Hiroki Kamiya, Hiroshi Funaki, Takehiro Kose
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Publication number: 20110095165Abstract: Disclosed herein are polymeric molds that can be used to make molded articles. The polymeric molds are made from cyclic olefin polymers that may be formed by ring opening metathesis polymerization (ROMP) of a polycyclic monomer having two or more reactive double bonds and a cyclic monomer comprising one reactive double bond. Fluorinated monomers may be used. The polymeric molds may be structured molds in that they have at least one microstructured feature having a dimension of less than about 2 mm, or less than about 500 um. The polymeric molds may also have a plurality of such microstructured features. Also disclosed herein are methods of making the polymeric molds, methods of making molded articles therefrom, and the molded articles.Type: ApplicationFiled: April 28, 2009Publication date: April 28, 2011Inventors: Joseph D. Rule, Kevin M. Lewandowski
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Patent number: 7875208Abstract: Disclosed herein is a conductive copolymer. The conductive copolymer can prevent water-absorbance, lower the concentration of polyacid contained in a molecule and exhibit superior film characteristics and excellent storage stability via a reduction in aggregation between molecules, as well as impart improved efficiency and lifetime to optoelectronic devices. The conductive copolymer includes a conductive polymer doped with a polyacid copolymer represented by Formula 1 below: Further disclosed are a conductive copolymer composition, a conductive copolymer composition film and an organic optoelectronic device, each including the conductive copolymer.Type: GrantFiled: November 8, 2007Date of Patent: January 25, 2011Assignee: Cheil Industries Inc.Inventors: Dal Ho Huh, Jeong Woo Lee, Mi Young Chae, Tae Woo Lee
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Publication number: 20100237294Abstract: A conductive polymer compound includes: a conductive polymer; a first repeating unit represented by the following Chemical Formula 1; a second repeating unit represented by the following Chemical Formula 2; and a third repeating unit represented by the following Chemical Formula 3 and/or Chemical Formula 4,Type: ApplicationFiled: June 1, 2010Publication date: September 23, 2010Inventors: Jeong-Woo Lee, Dal-Ho Huh, Mi-Young Chae, Tae-Woo Lee, Eui-Su Kang
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Publication number: 20100021960Abstract: Compositions, methods and related apparatus, as can be used for selective pathogen detection and identification.Type: ApplicationFiled: November 17, 2008Publication date: January 28, 2010Inventors: Vincent Rotello, Uwe Bunz, Ronnie Phillips, Oscar Miranda, Chang-Cheng You
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Publication number: 20100016531Abstract: Methods of making fluoropolymers from at least one fluoromonomerin either (1) a heterogeneous medium comprising a carbon dioxide and an aqueous phase with or without hydrocarbon surfactants or dispersants or stabilizer, or (2) a homogenous medium containing carbon dioxide with one or more organic solvents, are described.Type: ApplicationFiled: August 8, 2007Publication date: January 21, 2010Inventors: Libin Du, Joseph M. DeSimone
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Patent number: 7582704Abstract: Biomedical devices formed from a polymerization product of a monomeric mixture comprising one or more monomers comprising at least two trifluorovinyl groups are provided. Also provided are biomedical devices formed from a network of a polymer comprising one or more perfluorocyclobutane rings in the polymer backbone wherein the network is formed by crosslinks in the polymer.Type: GrantFiled: July 1, 2005Date of Patent: September 1, 2009Assignee: Bausch & Lomb IncorporatedInventors: Derek Schorzman, Joseph C. Salamone
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Publication number: 20090186998Abstract: Fluorinated paracyclophane compounds represented by the formula: where least one of R1 and R2 comprises a fluorinated moiety is disclosed. These compounds can be utilized as precursor dimer compounds to produce polymeric coatings comprising copolymers of trifluorinated paraxylylene, including flexible fluorinated paraxylylene coatings.Type: ApplicationFiled: December 9, 2008Publication date: July 23, 2009Applicant: SPECIALTY COATING SYSTEMS, INC.Inventors: Phillip Hanefeld, Sven Horst, Markus Meise, Michael Bognitzki, Andreas Greiner, Rakesh Kumar
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Patent number: 7563558Abstract: The present invention provides polymers that are useful in negative resist compositions. Polymers of the present invention comprise (1) a first monomer having a polar functional group; (2) a second monomer; and optionally, (3) a third monomer that imparts at least one characteristic selected from crosslinkable functionality, etch resistance, and solubility modulation. The first monomer provides an acid catalyzed polarity switch upon elimination of the polar functional group, whereas, the second monomer provides aqueous dissolution. The polymers of the present invention may be incorporated into negative resist compositions, which may also include photoacid generators, crosslinking agents, basic compounds, solvents, dissolution accelerators, photobase generators, latent basic compounds, surfactants, adhesion promoters, and anti-foaming agents.Type: GrantFiled: October 25, 2007Date of Patent: July 21, 2009Assignee: International Business Machines CorporationInventors: Robert David Allen, Gregory Breyta, Phillip Joe Brock, Richard A. DiPietro, David R. Medeiros, Ratnam Sooriyakumaran
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Patent number: 7534836Abstract: Biomedical devices are provided herein which are formed from a polymerization product of a monomeric mixture comprising one or more monomers comprising one or more trifluorovinyl groups, e.g., a perfluorocyclobutane containing polymer.Type: GrantFiled: July 1, 2005Date of Patent: May 19, 2009Assignee: Bausch & Lomb IncorporatedInventors: Derek Schorzman, Joseph C. Salamone
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Patent number: 7439302Abstract: A new underlayer composition that exhibits high etch resistance and improved optical properties is disclosed. The underlayer composition comprises a vinyl or acrylate polymer, such as a methacrylate polymer, the polymer comprising at least one substituted or unsubstituted naphthalene or naphthol moiety, including mixtures thereof. Examples of the polymer of this invention include: where each R1 is independently selected from an organic moiety or a halogen; each A is independently a single bond or an organic moiety; R2 is hydrogen or a methyl group; and each X, Y and Z is an integer of 0 to 7, and Y+Z is 7 or less. The organic moiety mentioned above may be a substituted or unsubstituted hydrocarbon selected from the group consisting of a linear or branched alkyl, halogenated linear or branched alkyl, aryl, halogenated aryl, cyclic alkyl, and halogenated cyclic alkyl, and any combination thereof.Type: GrantFiled: August 2, 2005Date of Patent: October 21, 2008Assignee: International Business Machines CorporationInventors: Wu-Song Huang, Sean D. Burns, Mahmoud Khojasteh
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Patent number: 7393624Abstract: The present invention provides polymers that are useful in negative resist compositions. Polymers of the present invention comprise (1) a first monomer having a polar functional group; (2) a second monomer; and optionally, (3) a third monomer that imparts at least one characteristic selected from crosslinkable functionality, etch resistance, and solubility modulation. The first monomer provides an acid catalyzed polarity switch upon elimination of the polar functional group, whereas, the second monomer provides aqueous dissolution. The polymers of the present invention may be incorporated into negative resist compositions, which may also include photoacid generators, crosslinking agents, basic compounds, solvents, dissolution accelerators, photobase generators, latent basic compounds, surfactants, adhesion promoters, and anti-foaming agents.Type: GrantFiled: June 20, 2007Date of Patent: July 1, 2008Assignee: International Business Machines CorporationInventors: Robert David Allen, Gregory Breyta, Phillip Joe Brock, Richard A. DiPietro, David R. Medeiros, Ratnam Sooriyakumaran
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Patent number: 7300739Abstract: The present invention provides polymers that are useful in negative resist compositions. Polymers of the present invention comprise (1) a first monomer having a polar functional group; (2) a second monomer; and optionally, (3) a third monomer that imparts at least one characteristic selected from crosslinkable functionality, etch resistance, and solubility modulation. The first monomer provides an acid catalyzed polarity switch upon elimination of the polar functional group, whereas, the second monomer provides aqueous dissolution. The polymers of the present invention may be incorporated into negative resist compositions, which may also include photoacid generators, crosslinking agents, basic compounds, solvents, dissolution accelerators, photobase generators, latent basic compounds, surfactants, adhesion promoters, and anti-foaming agents.Type: GrantFiled: May 29, 2003Date of Patent: November 27, 2007Assignee: International Business Machines CorporationInventors: Robert David Allen, Gregory Breyta, Phillip Joe Brock, Richard A. DiPietro, David R. Medeiros, Ratnam Sooriyakumaran
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Patent number: 7285612Abstract: A trifluorostyrene and substituted vinyl compound based partially fluorinated copolymer, an ionic conductive polymer membrane including the same, and a fuel cell adopting the ionic conductive polymer membrane, wherein the partially fluorinated copolymer has formula (1): where each of R1, R2 and R3 is F, H or CH3; X is a hydroxy group or a trifluoromethyl group; m is an integer greater than zero; n is an integer greater than zero; and p, q and r are zero or integers greater than zero.Type: GrantFiled: December 22, 2005Date of Patent: October 23, 2007Assignee: Samsung SDI Co., Ltd.Inventor: Hae-kyoung Kim
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Patent number: 7271228Abstract: Ionic perfluorovinyl compounds and their uses as components of ionic conductors of the polymer type, of selective membranes or of catalysts. The compounds comprise at least one perfluorovinyl group and at least one group chosen from —O or one of the groups C?N, —C(C?N)2, —NSO2R or —C[SO2R]2 or a pentacyclic group comprising at least one N, C—C?N, CR, CCOR or CSO2R group. The compounds and/or their polymers are of use in the preparation of ionically conducting materials, electrolytes and selective membranes.Type: GrantFiled: January 12, 2005Date of Patent: September 18, 2007Assignees: ACEP Inc., Centre National de la Recherche Scientifique, Universite de MontrealInventors: Michel Armand, Christophe Michot
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Patent number: 7169869Abstract: A resist composition comprising a polymer containing vinyl sulfonate units having fluorinated hydrophilic groups as a base resin has excellent transparency, substrate adhesion and developer penetrability as well as plasma etching resistance, and is suited for lithographic microprocessing.Type: GrantFiled: July 13, 2005Date of Patent: January 30, 2007Assignees: Shin-Etsu Chemical Co., Ltd., Matsushita Electric Industrial Co., Ltd., Central Glass Co., Ltd.Inventors: Yuji Harada, Jun Hatakeyama, Yoshio Kawai, Masaru Sasago, Masayuki Endo, Shinji Kishimura, Kazuhiko Maeda, Michitaka Ootani, Haruhiko Komoriya
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Patent number: 7144965Abstract: The invention is directed to polymerizable vinyl compounds having halogenated aromatic groups and to a method of synthesizing such compounds. In particular, the invention is directed to polymerizable aromatic vinyl compounds wherein, except for the vinylic hydrogen atoms, aromatic C—H bonds are replaced by C—X bonds, where X is a halogen or other selected substituent having a de minimus number, if any, of C—H bonds; for example, without limitation, highly fluorinated fluoroalkanes. In addition, the compounds of the invention have a de minimus number, if any, of N—H and O—H bonds.Type: GrantFiled: December 20, 2004Date of Patent: December 5, 2006Assignee: Corning, IncorporatedInventors: Olivier Arnoud, Marc Moroni, Stephane Roux
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Patent number: 7094469Abstract: A porous or non-porous polymeric substrate having its surface modified with an immobilized fluorocarbon such as perfluorocarbon, polymeric composition is provided. The immobilized fluorocarbon is formed from a monomer having formula: [T—SO2Y—SO2T?]?M+ in which —T and T? are identical or different and comprise an organic radical bearing at least one active polymerization function such as an unsaturation or a ring that can be opened; —M+ comprises an inorganic cation.Type: GrantFiled: August 28, 2001Date of Patent: August 22, 2006Assignee: Mykrolis CorporationInventor: Wilson Moya
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Patent number: 7037950Abstract: A trifluorostyrene and substituted vinyl compound based partially fluorinated copolymer, an ionic conductive polymer membrane including the same, and a fuel cell adopting the ionic conductive polymer membrane, wherein the partially fluorinated copolymer has formula (1): where each of R1, R2 and R3 is F, H or CH3; X is a hydroxy group or a trifluoromethyl group; m is an integer greater than zero; n is an integer greater than zero; and p, q and r are zero or integers greater than zero.Type: GrantFiled: May 3, 2004Date of Patent: May 2, 2006Assignee: Samsung SDI Co., Ltd.Inventor: Hae-kyoung Kim
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Patent number: 7009016Abstract: New precursors and processes are disclosed for making fluorinated, low dielectric constant ? thin films that have higher dimensional stability and are more rigid than fluorinated poly (para-xylylenes). The fluorinated, low dielectric constant thin films can be prepared from reactions of an ethylenic-containing precursor with benzocyclobutane-, biphenyl- and/or dieneone-containing precursors. The fluorinated, low dielectric constant thin films are useful for fabrications of future <0.13 ?m integrated circuits (ICs). Using fluorinated, low-dielectric constant thin films prepared according to this invention, the integrity of the dielectric, copper (Cu) and barrier metals, such as Ta, can be kept intact; therefore improving the reliability of the IC.Type: GrantFiled: April 5, 2004Date of Patent: March 7, 2006Assignee: Dielectric Systems, Inc.Inventor: Chung J. Lee
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Patent number: 6946235Abstract: A resist composition comprising a polymer containing vinyl sulfonate units having fluorinated hydrophilic groups as a base resin has excellent transparency, substrate adhesion and developer penetrability as well as plasma etching resistance, and is suited for lithographic microprocessing.Type: GrantFiled: August 8, 2003Date of Patent: September 20, 2005Assignees: Shin-Etsu Chemical Co., Ltd., Matsushita Electric Industrial Co., Ltd., Central Glass Co., Ltd.Inventors: Yuji Harada, Jun Hatakeyama, Yoshio Kawai, Masaru Sasago, Masayuki Endo, Shinji Kishimura, Kazuhiko Maeda, Michitaka Ootani, Haruhiko Komoriya
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Patent number: 6891071Abstract: The invention is directed to polymerizable vinyl compounds having halogenated aromatic groups and to a method of synthesizing such compounds. In particular, the invention is directed to polymerizable aromatic vinyl compounds wherein, except for the vinylic hydrogen atoms, aromatic C—H bonds are replaced by C—X bonds, where X is a halogen or other selected substituent having a de minimus number, if any, of C—H bonds; for example, without limitation, highly fluorinated fluoroalkanes. In addition, the compounds of the invention have a de minimus number, if any, of N—H and O—H bonds.Type: GrantFiled: September 22, 2003Date of Patent: May 10, 2005Assignee: Corning IncorporatedInventors: Olivier Arnoud, Marc Moroni, Stephane Roux
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Patent number: 6878641Abstract: Precursor compositions for the CVD formation of low k dielectric films on a substrate, e.g., as an interlayer dielectric for fabrication of microelectronic device structures. The precursor composition includes a gaseous mixture of (i) at least one aromatic compound, (ii) an inert carrier medium and (iii) optionally at least one unsaturated constituent that is ethylenically and/or acetylenically unsaturated The unsaturated constituent can include either (a) a compound containing ethylenic unsaturation and/or acetylenic unsaturation, or (b) an ethylenically unsaturated and/or acetylenically unsaturated moiety of the aromatic compound (i) of the precursor composition. The low k dielectric film material may be usefully employed in integrated circuitry utilizing copper metallization, to achieve low RC time constants and superior microelectronic device performance.Type: GrantFiled: October 1, 2002Date of Patent: April 12, 2005Assignee: Advanced Technology Materials, Inc.Inventor: Neil H. Hendricks
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Patent number: 6858691Abstract: Ionic perfluorovinyl compounds and their uses as components of ionic conductors of the polymer type, of selective membranes or of catalysts. The compounds comprise at least one perfluorovinyl group and at least one group chosen from —O or one of the groups C?N, —C(C?N)2, —NSO2R or —C[SO2R]2 or a pentacyclic group comprising at least one N, C—C?N, CR, CCOR or CSO2R group. The compounds and/or their polymers are of use in the preparation of ionically conducting materials, electrolytes and selective membranes.Type: GrantFiled: July 1, 2003Date of Patent: February 22, 2005Assignees: Acep Inc., Centre National de la Recherche Scientifique, Universite de MontrealInventors: Michel Armand, Christophe Michot
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Patent number: 6818381Abstract: Compositions suitable for forming planarizing underlayers for multilayer lithographic processes are characterized by the presence of (A) a polymer containing: (i) cyclic ether moieties, (ii) saturated polycyclic moieties, and (iii) aromatic moieties for compositions not requiring a separate crosslinker, or (B) a polymer containing: (i) saturated polycyclic moieties, and (ii) aromatic moieties for compositions requiring a separate crosslinker. The compositions provide outstanding optical, mechanical and etch selectivity properties. The compositions are especially useful in lithographic processes using radiation less than 200 nm in wavelength to configure underlying material layers.Type: GrantFiled: December 21, 2001Date of Patent: November 16, 2004Assignee: International Business Machines CorporationInventors: Mahmoud M. Khojasteh, Timothy M. Hughes, Ranee W. Kwong, Pushkara Rao Varanasi, William R. Brunsvold, Margaret C. Lawson, Robert D. Allen, David R. Medeiros, Ratnam Sooriyakumaran, Phillip Brock
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Patent number: 6797343Abstract: New precursors and processes are disclosed for making fluorinated, low dielectric constant ∈ thin films that have higher dimensional stability and are more rigid than fluorinated poly (para-xylylenes). The fluorinated, low dielectric constant thin films can be prepared from reactions of an ethylenic-containing precursor with benzocyclobutane-, biphenyl- and/or dieneone-containing precursors. The fluorinated, low dielectric constant thin films are useful for fabrications of future <0.13 &mgr;m integrated circuits (ICs). Using fluorinated, low-dielectric constant thin films prepared according to this invention, the integrity of the dielectric, copper (Cu) and barrier metals, such as Ta, can be kept intact; therefore improving the reliability of the IC.Type: GrantFiled: December 20, 2001Date of Patent: September 28, 2004Assignee: Dielectric Systems, Inc.Inventor: Chung J. Lee
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Patent number: 6774150Abstract: A trifluorostyrene and substituted vinyl compound based partially fluorinated copolymer, an ionic conductive polymer membrane including the same, and a fuel cell adopting the ionic conductive polymer membrane, wherein the partially fluorinated copolymer has formula (1): where each of R1, R2 and R3 is F, H or CH3; X is a hydroxy group or a trifluoromethyl group; m is an integer greater than zero; n is an integer greater than zero; and p, q and r are zero or integers greater than zero.Type: GrantFiled: July 2, 2001Date of Patent: August 10, 2004Assignee: Samsung Electronics Co., Ltd.Inventor: Hae-Kyoung Kim
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Patent number: 6765027Abstract: Ion-exchange materials comprising a polymeric backbone and a plurality of pendent styrenic or fluoridated styrenic macromonomers covalently bonded thereto, wherein the plurality of pendent styrenic or fluorinated styrenic macromonomers comprise a uniform number of styrenic or fluoridated styrenic monomer repeat units, and wherein predominantly all of the styrenic or fluoridated styrenic monomer repeat units have at least one charged group. Processes for making such material, as well as products related thereto, are also disclosed. In a representative embodiment, the ion-exchange material is utilized as a proton-exchange membrane (PEM) for use in a PEM fuel cell.Type: GrantFiled: May 13, 2002Date of Patent: July 20, 2004Assignee: Ballard Power Systems Inc.Inventors: Steven Holdcroft, Jianfu Ding, Carmen Chuy, Charles Stone, Anne E Morrison
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Patent number: 6660820Abstract: A new class of fluorinated arylacetylene compounds useful as monomers in the formation of polymers having low dielectric constant. These polymers, which are the reaction products of one of the fluorinated arylacetylene compounds, a diphenyl oxide biscyclopentadienone and, optionally, 1,3,5-tris(phenylacetylene)benzene, are useful in insulating microelectric device.Type: GrantFiled: July 24, 2002Date of Patent: December 9, 2003Assignee: International Business Machines CorporationInventors: Arthur Martin, Wei-Tsu Tseng
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Patent number: 6653515Abstract: &agr;,&bgr;,&bgr;-Trifluorostyrene and derivatives thereof synthesized in two steps from 1,1,1,2-tetrafluoroethylene. In the first step, 1,1,1,2-tetrafluoroethylene is reacted with a base, a metal salt such as zinc chloride and an optionally amine to form a trifluorovinyl metal complex. In the second step, the trifluorostyrene or derivative is obtained by reacting the trifluorovinyl metal complex with an aryl transfer agent such as, for example, an aryl triflate or an aryl halide, in the presence of a metal catalyst and optionally a coordinating ligand. Both steps may be carried out in one reactor.Type: GrantFiled: December 14, 2001Date of Patent: November 25, 2003Assignee: Ballard Power Systems Inc.Inventors: Charles Stone, Timothy J. Peckham, Donald J. Burton, Anilkumar Raghavanpillai
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Patent number: 6653047Abstract: Photoresist monomers, photoresist polymers prepared therefrom, and photoresist compositions using the polymers are disclosed. More specifically, photoresist polymers comprising a photoresist monomer containing fluorine-substituted benzylcarboxylate represented by Formula 1, and a composition comprising the polymer are disclosed. The photoresist composition has excellent etching resistance, heat resistance and adhesiveness, and can be developed in aqueous tetramethylammonium hydroxide (TMAH) solution. And, the present photoresist composition is suitable to form a fine pattern using deep ultraviolet light source such as VUV (157 nm), since the composition has low light absorbance at 193 nm and 157 nm wavelength. wherein, X1, X2, R1, l and m are defined in the specification.Type: GrantFiled: March 27, 2002Date of Patent: November 25, 2003Assignee: Hynix Semiconductor IncInventors: Geun Su Lee, Jae Chang Jung, Ki Soo Shin
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Synthesis of alpha, beta, beta-trifluorostyrene via in-situ formation of trifluorovinyl metal halide
Publication number: 20030144439Abstract: &agr;,&bgr;,&bgr;-Trifluorostyrene and derivatives thereof synthesized in two steps from 1,1,1,2-tetrafluoroethylene. In the first step, 1,1,1,2-tetrafluoroethylene is reacted with a base, a metal salt such as zinc chloride and an optionally amine to form a trifluorovinyl metal complex. In the second step, the trifluorostyrene or derivative is obtained by reacting the trifluorovinyl metal complex with an aryl transfer agent such as, for example, an aryl triflate or an aryl halide, in the presence of a metal catalyst and optionally a coordinating ligand. Both steps may be carried out in one reactor.Type: ApplicationFiled: December 14, 2001Publication date: July 31, 2003Applicant: Ballard Power Systems Inc.Inventors: Charles Stone, Timothy J. Peckham, Donald J. Burton, Anilkumar Raghavanpillai -
Publication number: 20030023014Abstract: Fluoropolymers consisting of alternating perfluorocyclobutane and aryl ether linkages possess suitable properties for optical waveguides and other devices using refractive properties of the polymers. Perfluorocyclobutane (PFCB) polymers having aryl groups alternating on an ether chain have shown useful physical properties for optical waveguide applications. Processes for micromolding such polymeric films by replicating a pattern or image directly from a silicon master, rather than from a polydimethyl siloxane (PDMS) mold, are disclosed.Type: ApplicationFiled: August 7, 2002Publication date: January 30, 2003Inventors: Dennis W. Smith, Hiren V. Shah, John Ballato, Stephen Foulger
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Patent number: 6461790Abstract: Polymers comprising fluorinated vinyl phenol units and having acid labile groups partially introduced are novel. Using such polymers, resist compositions featuring transparency to excimer laser and alkali solubility are obtained.Type: GrantFiled: September 8, 2000Date of Patent: October 8, 2002Assignees: Shin-Etsu Chemical Co., Ltd., Mastsuchita Electric Industrial Co., Ltd.Inventors: Jun Hatakeyama, Jun Watanabe, Yuji Harada, Mutsuo Nakashima, Masaru Sasago, Shinji Kishimura
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Publication number: 20020137806Abstract: Graft polymeric membranes and methods for making graft polymeric membranes have one or more trifluorovinyl aromatic monomers that are radiation graft polymerized to a polymeric base film. The membranes comprise a polymeric base film to which has been graft polymerized substituted &agr;,&agr;,&bgr;-trifluorostyrene and/or &agr;,&agr;,&bgr;-trifluorovinylnaphthylene monomers, which are activated towards graft polymerization. As ion-exchange membranes, the membranes are suitable for use in electrode apparatus, including membrane electrode assemblies in, for example, fuel cells. The membranes can also be crosslinked.Type: ApplicationFiled: August 21, 2001Publication date: September 26, 2002Inventors: Charles Stone, Alfred E. Steck, Biswajit Choudhury
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Publication number: 20020120083Abstract: New precursors and processes to generate fluorinated poly(para-xylylenes) (“PPX”) and their chemically modified films suitable for fabrications of integrated circuits (“ICs”) of <0.15 &mgr;m are disclosed. The films so prepared have low dielectric constants (“∈”) and are able to keep the integrity of the dielectric, Cu, and the barrier metal, such as Ta. Hence, the reliability of ICs can be assured.Type: ApplicationFiled: February 26, 2001Publication date: August 29, 2002Inventor: Chung J. Lee