Bridged Monomer Patents (Class 526/281)
  • Patent number: 7015293
    Abstract: A cyclic olefin addition copolymer obtained by copolymerizing a cyclic olefin compound having a side chain substituent group with a ring structure, such as endo-tricyclo[4.3.0.12,5]deca-3,7-diene or endo-tricyclo[4.3.0.12,5]deca-3-ene, with another cyclic olefin compound such as bicyclo[2.2.1]hept-2-ene, and further with a cyclic olefin compound having a hydrolysable silyl group as needed, or hydrogenating after copolymerization; a composition for crosslinking in which a specific crosslinking agent is incorporated; a crosslinked product obtained by crosslinking the composition; an optical material containing the copolymer, the composition or the crosslinked product; and a method for producing the copolymer in which addition polymerization is conducted using a specific nickel catalyst.
    Type: Grant
    Filed: May 14, 2003
    Date of Patent: March 21, 2006
    Assignee: JSR Corporation
    Inventors: Noboru Oshima, Tatsuya Sakai, Kenzo Ohkita, Takashi Tsubouchi
  • Patent number: 7015291
    Abstract: Process for producing photoresist polymeric compound having repeated units corresponding to at least one monomer selected from monomer (a) having lactone skeleton, monomer (b) having group which becomes soluble in alkali by elimination with acid, and monomer (c) having alicyclic skeleton having hydroxyl group. Process includes (A) polymerizing mixture of monomers containing at least one monomer selected from the above monomers (a), (b), and (c), and (B) extracting polymer formed in the polymerization by using organic solvent and water to partition the formed polymer into organic solvent layer and metal component impurity into aqueous layer, or passing polymer solution, which contains polymer having repeated units corresponding to at least one of the above monomers (a), (b), and (c) and metal content of which is 1000 ppb by weight or less relative to the polymer through filter comprising porous polyolefin membrane having cation-exchange group.
    Type: Grant
    Filed: March 14, 2003
    Date of Patent: March 21, 2006
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Hitoshi Watanabe, Hidetaka Hayamizu, Masaaki Kishimura
  • Patent number: 7001707
    Abstract: A resist composition comprising a blend of a cyclic polymer having alcoholic groups as soluble groups and a polymer having carboxyl or hexafluoroalcohol groups whose hydrogen atoms are replaced by acid labile groups as a base resin forms a resist film which is improved in transparency, alkali dissolution contrast and plasma etching resistance.
    Type: Grant
    Filed: August 25, 2004
    Date of Patent: February 21, 2006
    Assignees: Shin-Etsu Chemical Co., Ltd., Matsushita Electric Industrial Co., Ltd., Central Glass Co., Ltd.
    Inventors: Jun Hatakeyama, Yuji Harada, Yoshio Kawai, Masaru Sasago, Masayuki Endo, Shinji Kishimura, Kazuhiko Maeda, Haruhiko Komoriya, Kazuhiro Yamanaka
  • Patent number: 6998450
    Abstract: The present invention provides a method for preparing homo- and co-polymers by polymerizing cyclic olefin compounds using addition polymerization. The method can produce a cyclic olefin polymer having a high molecular weight with a high yield in the presence of, as an addition polymerization catalyst, a complex prepared by mixing a nickel salt compound and an organoaluminoxane compound with at least one fluorine-containing aromatic hydrocarbon compound represented by the following formula 1 or 2 as a catalyst activator: C6RmH6-mFormula 1 where R is CF3; and m is from 1 to 3, or C6FnH6-nFormula 2 where n is from 1 to 6.
    Type: Grant
    Filed: January 11, 2005
    Date of Patent: February 14, 2006
    Assignee: Korea Kumho Petrochemical Co., Ltd.
    Inventors: Young Chan Jang, Hyun Kyung Sung
  • Patent number: 6995226
    Abstract: A ring-opened metathesis copolymer and its hydrogenated product having a desired monomer unit ratio and a high molecular weight and having hydroxyl groups or hydroxycarbonyl groups can be obtained by conducting a ring-opening metathesis copolymerization of a norbornene-type monomer having hydroxyl groups or hydroxycarbonyl groups with an unsubstituted norbornene-type monomer having at least three rings in the presence of a catalyst predominantly comprised of an organic ruthenium compound having coordinated therewith a neutral electron-donating ligand, and, if desired, hydrogenating the resulting copolymer. The thus-obtained ring-opened metathesis copolymer and its hydrogenation product are characterized by having a low water absorption, good adhesion to metal and other materials, good compatibility with a curing agent and other compounds, and high heat resistance, and exhibiting reduced signal retardation and signal noise.
    Type: Grant
    Filed: June 5, 2002
    Date of Patent: February 7, 2006
    Assignee: Zeon Corporation
    Inventors: Kazunori Taguchi, Yasuo Tsunogae, Hitomi Takeuchi, Yasuhiro Wakisaka, Kei Sakamoto
  • Patent number: 6992154
    Abstract: The present invention provides a cyclic olefin addition copolymer which has a reactive silyl group having a specific structure, excels in optical transparency, heat resistance, and adhesion, and is capable of producing a crosslinked product having improved dimensional stability, solvent resistance, and chemical resistance. The present invention also provides a process for producing the cyclic olefin addition copolymer, a crosslinking composition, a crosslinked product and a process for producing the same, and an optically transparent material (transparent resin film) comprising the cyclic olefin addition copolymer. The optically transparent material excels in optical transparency and heat resistance, exhibits improved dimensional stability, adhesion, solvent resistance, and chemical resistance, and is capable of improving fragility and preventing occurrence of cracks in the film.
    Type: Grant
    Filed: October 21, 2004
    Date of Patent: January 31, 2006
    Assignee: JSR Corporation
    Inventors: Noboru Oshima, Yooichiroh Maruyama, Michitaka Kaizu, Katsutoshi Sawada, Toshihiro Hayashi, Kenzo Ohkita
  • Patent number: 6987156
    Abstract: A film and method for fastening cargo during transportation wherein the film has a percentage strain change 100 hours after applying a load of 3.5 MPa at a temperature of 23° C. of not more than 2.0%, and a percentage strain change 100 hours after applying a load of 0.5 MPa at a temperature of 55° C. of not more than 2.5%. Moreover, it is preferable for the elastic modulus at a temperature of 23° C. to be not more than 60 MPa, and the elastic modulus at a temperature of 55° C. to be not more than 20 MPa. Such a film can be formed from substantially random interpolymer(s) each comprising 1 to 99 mol % of polymer units derived from an aromatic vinyl or vinylidene monomer and/or a hindered aliphatic or cycloaliphatic vinyl or vinylidene monomer, and 1 to 99 mol % of polymer units derived from at least one ?-olefin having 2 to 20 carbon atoms.
    Type: Grant
    Filed: June 24, 2003
    Date of Patent: January 17, 2006
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Masashi Arimoto, Tomohiko Kimura, Saburou Takeyama
  • Patent number: 6982302
    Abstract: An automotive molding, which is excellent in scratching resistance, has high gloss, and is excellent in weathering resistance. The automotive molding of the invention has a part composed of an elastomer material containing an olefinic random copolymer obtained by copolymerizing ethylene, an ?-olefin having 3 to 10 carbon atoms and an unsaturated monomer having a functional group, and optionally a non-conjugated diene, and a metal ion for crosslinking the olefinic random copolymer.
    Type: Grant
    Filed: December 24, 2003
    Date of Patent: January 3, 2006
    Assignee: JSR Corporation
    Inventors: Kentarou Kanae, Toshiyuki Hayakawa, Minoru Tanaka, Akihiko Morikawa
  • Patent number: 6977284
    Abstract: It is an object of the present invention to provide a polymerizable composition and a cured resin composition, linear expansion coefficients of which are significantly improved without impairment of the excellent properties such as heat resistance, mechanical strength and the like of norbornene-based resins. The present invention is a polymerizable composition, which comprises a polymerizable substance containing a norbornene-based monomer or oligomer as a main component, a metathesis polymerization catalyst and silica powder, the weight content of the silica powder being larger than the weight content of the polymerizable substance.
    Type: Grant
    Filed: February 17, 2003
    Date of Patent: December 20, 2005
    Assignee: Sekisui Chemical Co., Ltd.
    Inventors: Takeharu Morita, Nobuhiro Goto, Hiroshi Yoshitani, Hiroshi Hiraike
  • Patent number: 6974657
    Abstract: A fluorine-containing polymer prepared from at least a spacer group selected from the group consisting of ethylene, alpha-olefins, 1,1?-disubstituted olefins, vinyl alcohols, vinyl ethers, and 1,3-dienes; and a norbornyl radical containing a functional group containing the structure: —C(Rf)(Rf?)Orb wherein Rf and Rf? are the same or different fluoroalkyl groups of from 1 to about 10 carbon atoms or taken together are (CF2)n wherein n is an integer ranging from 2 to about 10 and Rb is a hydrogen atom or an acid- or base-labile protecting group; r is an integer ranging from 0-4. The fluorine-containing polymer has an absorption coefficient of less than 4.0 mm?1 at a wavelength of 157 nm. These polymers are useful in photoresist compositions for microlithography. They exhibit high transparency at this short wavelength and also possess other key properties, including good plasma etch resistance and adhesive properties.
    Type: Grant
    Filed: October 16, 2001
    Date of Patent: December 13, 2005
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Larry L. Berger, Michael Karl Crawford, Jerald Feldman, Lynda Kaye Johnson, Frank Leonard Schadt, III, Fredrick Claus Zumsteg, Jr.
  • Patent number: 6969751
    Abstract: The present invention relates to a method for preparing homo- and co-polymers having high molecular weights in high yields by polymerizing cyclic olefin compounds using a complex prepared by mixing a nickel salt compound, an organoaluminoxane compound, and at least one fluorine-containing compound.
    Type: Grant
    Filed: November 24, 2004
    Date of Patent: November 29, 2005
    Assignee: Korea Kumho Petrochemical Co., Ltd.
    Inventors: Young Chan Jang, Hyun Kyung Sung, Eun Joo Park
  • Patent number: 6956090
    Abstract: A method of obtaining homopolymers and/or copolymers in aqueous solution by the use of phosphorous acid and/or its salts or sodium hypophosphite and by neutralization during the polymerisation of the ethylenically unsaturated monomers by the continuous addition, first of all, of bases such as sodium hydroxide, potassium hydroxide or lithium hydroxide and then bases of alkaline earths such as calcium hydroxide, magnesium hydroxide, calcium oxide or magnesium oxide. The polymers obtained by the said method and uses thereof.
    Type: Grant
    Filed: September 13, 2000
    Date of Patent: October 18, 2005
    Assignee: Coatex S.A.
    Inventors: Jean-Marc Suau, Christian Jacquemet, Jean-Bernard Egraz, Jacques Mongoin
  • Patent number: 6946235
    Abstract: 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: Grant
    Filed: August 8, 2003
    Date of Patent: September 20, 2005
    Assignees: 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
  • Patent number: 6946233
    Abstract: Provided are a resist material having markedly high resolution and etching resistance of a practically usable level, and being useful for fine microfabrication; a patterning method using the resist material; and a polymer useful as a base resin for the resist material. More specifically, provided are a polymer having a weight-average molecular weight of 1,000 to 500,000, which comprises one or more repeating units selected from the group consisting of repeating units represented by formulae (1) to (3) below; and one or more repeating units of the formula (4) below; and a resist material containing the polymer.
    Type: Grant
    Filed: July 22, 2002
    Date of Patent: September 20, 2005
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Tsunehiro Nishi, Takeshi Kinsho
  • Patent number: 6946523
    Abstract: In accordance with the present invention, there are provided novel heterobifunctional monomers and users for the same. Invention compounds have many of the properties required by the microelectronics industry, such as, for example, hydrophobicity, high Tg values, low dielectric constant, ionic purity, low coefficient of thermal expansion (CTE), and the like. These properties result in a thermoset that is particularly well suited to high performance applications where typical operating temperatures are often significantly higher than those at which prior art materials were suitable. Invention compounds are particularly ideal for use in the manufacture of electronic components, such as, for example, printed circuit boards, and the like.
    Type: Grant
    Filed: July 1, 2003
    Date of Patent: September 20, 2005
    Assignee: Henkel Corporation
    Inventors: Stephen M. Dershem, Kevin J. Forrestal, Puwei Liu
  • Patent number: 6939662
    Abstract: A positive-working resist composition comprising: (A1) a resin containing a repeating unit represented by the specific formula, which increases the solubility in an alkali developing solution by the action of an acid, and (B) a compound capable of generating an acid upon irradiation with one of actinic rays and radiation.
    Type: Grant
    Filed: May 30, 2003
    Date of Patent: September 6, 2005
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kazuyoshi Mizutani, Shinichi Kanna, Tomoya Sasaki
  • Patent number: 6936672
    Abstract: A catalyst system and a process for the bulk addition polymerization or of polycyclic olefins, such as norbornene, methylnorbornene, ethylnorbornene, butylnorbornene or hexylnorbornene, 1,2,3,4,4a,5,8,8a-octahydro-1,4:5,8-dimethanonapthalene, 5,5?-(1,2-ethanediyl)bisbicyclo[2.2.1]hept-2-ene, and 1,4,4a,4b,5,8,8a,8b-octahydro-1,4:5,8-dimethanobiphenylene are disclosed. The catalyst includes an organonickel or organopalladium transition metal procatalyst and an activator compound. Polymerization can be carried out in a reaction injection molding process to yield thermoplastic and thermoset molded polymeric articles possessing high glass transition temperatures.
    Type: Grant
    Filed: August 2, 2001
    Date of Patent: August 30, 2005
    Assignee: Sumitomo Bakelite Co., Ltd.
    Inventors: Andrew Bell, Larry F. Rhodes, Brian L. Goodall, John C. Fondran, Lester H. Mclntosh, III, Dennis A. Barnes
  • Patent number: 6936402
    Abstract: Disclosed herein is a novel norbornene, acrylate or methacrylate monomer as a photoresist monomer containing an oxepan-2-one group. Further disclosed are photoresist compositions comprising a polymer prepared from the monomer, methods for preparing the photoresist compositions, and methods for forming photoresist patterns using the photoresist compositions.
    Type: Grant
    Filed: February 24, 2004
    Date of Patent: August 30, 2005
    Assignee: Korea Advanced Institute Science & Technology
    Inventors: Jin-Baek Kim, Tae-Hwan Oh, Jae-Hak Choi, Jae-Jun Lee
  • Patent number: 6936350
    Abstract: The present application relates to a white, biaxially oriented, flame-retardant, UV-resistant polyester film with at least one base layer which comprises, based on the weight of the base layer, from 2 to 60% by weight of a cycloolefin copolymer (COC), where the glass transition temperature of the COC is within the range from 70 to 270° C. The film also comprises from 0.01 to 5.0% by weight of a UV stabilizer as light stabilizer and also comprises from 0.5 to 30% by weight of flame retardant, based in each case on the weight of the layer comprising the UV stabilizer and/or comprising the flame retardant. The film of the invention is suitable for packing foods or other consumable items which are sensitive to light and/or to air, or for use in industry, e.g. in the production of hot-stamping foils or as a label film, or for image-recording papers, printed sheets or magnetic recording cards.
    Type: Grant
    Filed: February 12, 2001
    Date of Patent: August 30, 2005
    Assignee: Mitsubishi Polyester Film GmbH
    Inventors: Ursula Murschall, Herbert Peiffer, Gottfried Hilkert, Hans Mahl
  • Patent number: 6933096
    Abstract: A photosensitive polymer including fluorine, a resist composition containing the same and a patterning method for IC fabrication using the resist composition are provided. The photosensitive polymer having at least one selected from the group consisting of fluorine-substituted or unsubstituted alkyl ester, tetrahydropyranyl ester, tetrahydrofuranyl ester, nitrile, amide, carbonyl and hexafluoro alkyl having a hydrophilic group, and a trifluorovinyl derivative monomer as a repeating unit and having a weight average molecular weight of about 3,000 to about 100,000. The photosensitive polymer exhibits high transmittance for a light source of F2 (157 nm), high dry etching resistance, and has characteristics suitable to realize an unitrafine pattern size.
    Type: Grant
    Filed: November 21, 2003
    Date of Patent: August 23, 2005
    Assignee: Samsung Electronics, Co., Ltd.
    Inventors: Kwang-Sub Yoon, Ki-Yong Song
  • Patent number: 6930157
    Abstract: A catalyst composition for preparing olefin polymers. The catalyst composition includes a metallocene compound and an activating cocatalyst. In the metallocene compound, two cyclopentadienyl groups are bridged by X (carbon, silicon, germanium or tin) in a ring structure. The bite angle ? formed by the two cyclopentadienyl rings and X is equal to or greater than 100 degrees. The obtained olefin polymer has high cycloolefin conversion and a high glass transition temperature. In addition, the catalyst composition can still maintain relatively high activity at high temperature reaction conditions.
    Type: Grant
    Filed: June 12, 2003
    Date of Patent: August 16, 2005
    Assignee: Industrial Technology Research Institute
    Inventors: Jing-Cherng Tsai, Ming-Yuan Wu, Tung-Ying Hsieh, Yuh-Yuan Wei, Chao-Ying Yu
  • Patent number: 6924078
    Abstract: Photoresist monomers, polymers thereof, photoresist compositions containing the same for preventing acid generated in the exposed area during the course of a photolithography process from being diffused to the unexposed area. The line edge roughness and slope pattern are improved when an ultrafine photoresist pattern is formed using photoresist copolymer having a multi-oxygen-containing compound as a repeating unit such as an ethyleneoxy moiety represented by Formula 1 with at least one polymerizable carbon-carbon double bond. In addition, the shape of pattern is improved by eliminating top loss and the adhesion of pattern to the substrate is improved. wherein n is an integer ranging from 1 to 5.
    Type: Grant
    Filed: August 22, 2002
    Date of Patent: August 2, 2005
    Assignees: Hynix Semiconductor Inc., Dongjin Semichem Co., Ltd.
    Inventors: Geun Su Lee, Jae Chang Jung, Ki Soo Shin, Se Jin Choi, Deog Bae Kim, Jae Hyun Kim
  • Patent number: 6924339
    Abstract: Thermally cured undercoat for use in lithography of a thermally cured composition comprising a hydroxyl-containing polymer, an amino cross-linking agent and a thermal acid generator, wherein the hydroxyl containing polymer is a polymer comprising units m, n and o of the following formula: wherein R1 is H or methyl; R2 is a substituted or unsubstituted C6-C14 aryl acrylate or C6-C14 aryl methacrylate group wherein the substituted groups may be phenyl, C1-4 alkyl or C1-4 alkoxy; R3 is a hydroxyl functionalized C1-C8 alkyl acrylate, methacrylate or C6-C14 aryl group, R4 is a C1-C10 linear or branched alkylene; p is an integer of from 1 to 5 with the proviso that there are no more than thirty carbon atoms in the [—R4O—]p; R5 is a C1-C10 linear, branched or cyclic alkyl, substituted or unsubstituted C6-C14 aryl, or substituted or unsubstituted C7-C15 alicyclic hydrocarbon; and m is about 40 to 70, n is about 15 to 35 and o is about 15 to 25.
    Type: Grant
    Filed: May 14, 2003
    Date of Patent: August 2, 2005
    Assignee: Arch Specialty Chemicals, Inc.
    Inventors: Binod B. De, Sanjay Malik, Gregory Spaziano, John Joseph Biafore, Patrick Foster, Sidney George Slater, Thomas Steinhausler, Andrew J. Blakeney
  • Patent number: 6921622
    Abstract: Photoresist monomers of following Formula 1, photoresist polymers thereof, and photoresist compositions containing the same. The photoresist polymer includes a repeating unit comprising the photoresist monomer of Formula 1 as a comonomer and the photoresist composition containing the same have excellent etching resistance, heat resistance and adhesiveness to a wafer, and is developable in aqueous tetramethylammonium hydroxide (TMAH) solution.
    Type: Grant
    Filed: January 22, 2002
    Date of Patent: July 26, 2005
    Assignee: Hynix Semiconductor Inc.
    Inventors: Geun Su Lee, Jae Chang Jung, Ki Soo Shin
  • Patent number: 6916592
    Abstract: A resist composition comprising a base polymer having a fluorinated sulfonate or fluorinated sulfone introduced therein is sensitive to high-energy radiation, has excellent transparency, contrast and adherence, and is suited for lithographic microprocessing.
    Type: Grant
    Filed: March 25, 2003
    Date of Patent: July 12, 2005
    Assignees: 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
  • Patent number: 6914109
    Abstract: The invention relates to a process for the preparation of 15-pentadecanolide by hydrogenating 15-pentadecenolide and to its use.
    Type: Grant
    Filed: March 18, 2002
    Date of Patent: July 5, 2005
    Assignee: Symrise GmbH & Co. KG
    Inventors: Walter Kuhn, Oskar Koch, Hans-Ulrich Funk, Gerhard Senft
  • Patent number: 6914112
    Abstract: An ethylene-based copolymer is useful as a modifier for resins, e.g., polypropylene, and can be used in an ethylene/?-olefin copolymer composition containing the same ethylene-based copolymer. The inventive copolymer is characterize by: (a-1) having temperature (Tm) at the maximum peak in the endothermic curve, measured by a differential scanning calorimeter (DSC), of 40 to 90° C., (a-2) containing the component soluble in decane at normal temperature at 1 to 70% b weight, and (a-3) containing the component soluble in decane at normal temperature which comprises (i) a recurring unit derived from ethylene and (ii) a recurring unit derived from an ?-olefin of 4 or more carbon atoms, and in which a content of (i) the recurring unit derived from ethylene is 50 to 75% by mole.
    Type: Grant
    Filed: May 15, 2001
    Date of Patent: July 5, 2005
    Assignee: Mitsui Chemical, Inc.
    Inventors: Ryoji Mori, Kouichi Kizu, Keiji Okada, Kazuyuki Takimoto
  • Patent number: 6911507
    Abstract: A cyclic olefin having a specific polar group is polymerized by addition polymerization in a hydrocarbon solvent, using a polymerization catalyst component containing (i) a specific transition metal compound, (ii) a Lewis acid compound and (iii) an alkyl aluminoxane, or the cyclic olefin is polymerized by addition polymerization in the hydrocarbon solvent, using the polymerization catalyst component, by further adding at least one aromatic vinyl compound and at least one cyclic nonconjugated polyene compound, or either one of them as a molecular weight modifier, thereby obtaining a cyclic olefinic addition polymer.
    Type: Grant
    Filed: January 23, 2001
    Date of Patent: June 28, 2005
    Assignee: JSR Corporation
    Inventors: Kenzo Ohkita, Noboru Oshima, Takashi Imamura, Takashi Tsubouchi
  • Patent number: 6908724
    Abstract: There is provided a novel fluorine-containing polymer having an acid-reactive group which has a high transparency against energy rays (radioactive rays) in a vacuum ultraviolet region (157 nm), and further there are provided a material for fluorine-containing base polymer prepared from the polymer and suitable for a photoresist and a chemically amplifying type resist composition obtained therefrom. The polymer has a number average molecular weight of from 1,000 to 1,000,000 and represented by the formula: —(M1)—(M2)—(A)—, wherein M1 is a structural unit having an acid-labile or acid-degradable functional group, M2 is a structural unit of fluorine-containing acryl ester, A is a structural unit derived from other copolymerizable monomer, the percent by mole ratio M1/M2 is 1 to 99/99 to 1 and the polymer comprises from 1 to 99% by mole of the structural unit M1, from 1 to 99% by mole of the structural unit M2 and from 0 to 98% by mole of the structural unit A1.
    Type: Grant
    Filed: October 3, 2002
    Date of Patent: June 21, 2005
    Assignee: Daikin Industries, Ltd.
    Inventors: Takayuki Araki, Meiten Koh, Yoshito Tanaka, Takuji Ishikawa, Hirokazu Aoyama, Tetsuo Shimizu
  • Patent number: 6908970
    Abstract: A process for producing a hydrogenated product of a polymer prepared through ring-opening polymerization which comprises a polymerization step of polymerizing a cyclic olefin through ring-opening polymerization in the presence of a polymerization catalyst comprising an organoruthenium compound or an organoosmium compound to prepare a polymer, and a hydrogenation step of adding a hydrogenation catalyst and hydrogen into a polymerization system resulting from the polymerization step to hydrogenate the carbon-carbon double bonds of the polymer prepared through the ring-opening polymerization. When the organoruthenium compound- or organoosmium compound-containing catalyst further comprises a carbene compound, the catalyst exhibits a higher activity for the ring-opening polymerization.
    Type: Grant
    Filed: October 7, 2002
    Date of Patent: June 21, 2005
    Assignee: Zeon Corporation
    Inventors: Yasuo Tsunogae, Masato Sakamoto, Masaharu Tokoro, Kazunori Taguchi
  • Patent number: 6903171
    Abstract: Methods for the addition polymerization of cycloolefins using a cationic Group 10 metal complex and a weakly coordinating anion of the formula: [(R?)zM(L?)x(L?)y]b[WCA]d wherein [(R?)zM(L?)x(L?)y] is a cation complex where M represents a Group 10 transition metal; R? represents an anionic hydrocarbyl containing ligand; L? represents a Group 15 neutral electron donor ligand; L? represents a labile neutral electron donor ligand; x is 1 or 2; and y is 0, 1, 2, or 3; and z is 0 or 1, wherein the sum of x, y, and z is 4; and [WCA] represents a weakly coordinating counteranion complex; and b and d are numbers representing the number of times the cation complex and weakly coordinating counteranion complex are taken to balance the electronic charge on the overall catalyst complex.
    Type: Grant
    Filed: October 15, 2002
    Date of Patent: June 7, 2005
    Assignee: Promerus, LLC
    Inventors: Larry Funderburk Rhodes, Andrew Bell, Ramakrishna Ravikiran, John C. Fondran, Saikumar Jayaraman, Brian Leslie Goodall, Richard A. Mimna, John-Henry Lipian
  • Patent number: 6884564
    Abstract: Fluorinated polymers, photoresists and associated processes for microlithography are described. These polymers and photoresists are comprised of esters derived from fluoroalcohol functional groups that simultaneously impart high ultraviolet (UV) transparency and developability in basic media to these materials. The materials of this invention have high UV transparency, particularly at short wavelengths, e.g., 157 nm, which makes them highly useful for lithography at these short wavelengths.
    Type: Grant
    Filed: October 25, 2002
    Date of Patent: April 26, 2005
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Andrew E. Feiring, Jerald Feldman, Frank L. Schadt, III, Gary Newton Taylor
  • Patent number: 6878501
    Abstract: Polymers comprising recurring units of cycloolefin having fluorinated alkyl introduced therein are novel and have transparency and alkali solubility. Using the polymers, resist compositions featuring low absorption of F2 excimer laser light are obtained.
    Type: Grant
    Filed: April 26, 2001
    Date of Patent: April 12, 2005
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Jun Watanabe, Yuji Harada
  • Patent number: 6875555
    Abstract: There is disclosed a composition comprising a mixture of endo- and exo-2-(bicyclo[2.2.1]hept-5-en-2-yl)-2,2-fluoroalkyl-ethan-2-ol which is rich in the exo isomer, preferably the endo/exo concentration ratio is no greater than 5/95. The composition is useful for forming a repeat unit of a polymer which polymer may further comprise additional repeat units derived-from tert-butyl acrylate, hydroxyadamantyl acrylate, protected or unprotected fluorinated-olefins, 2-methyl-2-adamantyl acrylate, 2-propenoic acid, 2-hydroxy-1,1,2-trimethylpropyl ester. Polymers of this invention are useful as the binder component of a photoresist composition for microlithography.
    Type: Grant
    Filed: September 16, 2003
    Date of Patent: April 5, 2005
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Andrew Edward Feiring, Viacheslav Alexandrovich Petrov, Frank Leonard Schadt, III
  • Patent number: 6872792
    Abstract: An adhesive or coating composition prepared by mixing together at least one metathesizable highly-reactive cycloolefin (e.g., a norbornadiene) and a metathesis catalyst. The use of highly-reactive cycloolefins can provide exceptional adherence to a low-surface-tension substrate. Another embodiment is a two-part adhesive or coating system wherein the first part includes at least one first metathesizable material, and the second part includes at least one liquid metathesis oligomer or polymer and a metathesis catalyst.
    Type: Grant
    Filed: June 25, 2001
    Date of Patent: March 29, 2005
    Assignee: Lord Corporation
    Inventors: Jonathan L. Kendall, Kenneth C. Caster
  • Patent number: 6872514
    Abstract: A resist composition comprising a base polymer having a fluorinated sulfonate or fluorinated sulfone introduced therein is sensitive to high-energy radiation below 300 nm, has excellent transparency, contrast and adherence, and is suited for lithographic microprocessing.
    Type: Grant
    Filed: March 25, 2003
    Date of Patent: March 29, 2005
    Assignees: 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
  • Patent number: 6866984
    Abstract: A photoresist copolymer is prepared from one or more carboxy-substituted bicycloalkene monomers, and this copolymer is used to prepare a photoresist for submicrolithography processes employing deep ultraviolet (ArF) as a light source. In addition to having high etch resistance and thermal resistance, the photoresist has good adhesiveness to the substrate and can be developed in a TMAH solution.
    Type: Grant
    Filed: December 18, 2003
    Date of Patent: March 15, 2005
    Assignee: Hyundai Electronics Industries Co., Ltd.
    Inventors: Jae Chang Jung, Cheol Kyu Bok, Ki Ho Baik
  • Patent number: 6858371
    Abstract: Photoresist monomers, photoresist polymers prepared thereof, and photoresist compositions using the polymer are disclosed. More specifically, photoresist polymers comprising maleimide monomer represented by Formula 1, and a composition comprising the polymer thereof are disclosed. The photoresist composition has excellent etching resistance, heat resistance and adhesiveness, and can be developed in an aqueous tetramethylammonium hydroxide (TMAH) solution. As the composition has low light absorbance at 193 nm and 157 nm wavelength, and it is suitable for a process using ultraviolet light source such as VUV (157 nm) wherein, X1, X2, R1, R2 and R3 are defined in the specification.
    Type: Grant
    Filed: February 21, 2002
    Date of Patent: February 22, 2005
    Assignee: Hynix Semiconductor Inc.
    Inventors: Geun Su Lee, Jae Chang Jung, Min Ho Jung, Cha Won Koh, Ki Soo Shin
  • Patent number: 6849378
    Abstract: A resist composition includes a photoacid generator (PAG) and a photosensitive polymer. The photosensitive polymer includes a comonomer having an acid-labile substituent group or a polar functional group, and a copolymer of alkyl vinyl ether and maleic anhydride. The copolymer is represented by the following structure: where k is an integer of 3 to 8, and where X is tertiary cyclic alcohol having 7 to 20 carbon atoms.
    Type: Grant
    Filed: April 17, 2002
    Date of Patent: February 1, 2005
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Sangjun Choi, Hyunwo Kim, Joontae Moon, Sanggyun Woo
  • Patent number: 6846890
    Abstract: A novel norbornene derivative represented by a general formula (1m) shown below is provided. By conducting a ring opening polymerization of this norbornene derivative, or by performing a subsequent hydrogenation following the ring opening polymerization, a ring opening polymer or a hydrogenated product thereof with an excellent low birefringence can be obtained. [wherein, at least one of R1 to R4 is a group selected from the group consisting of groups represented by a general formula (1-1) shown below and groups represented by a general formula (1-2) shown below] [wherein, at least one of RA, RB and Z is a group represented by the formula —C(O)O—].
    Type: Grant
    Filed: October 8, 2002
    Date of Patent: January 25, 2005
    Assignee: JSR Corporation
    Inventors: Nobuyuki Miyaki, Yoshikazu Miyamoto, Seiji Fukuhara, Toshihiro Ootsuki
  • Patent number: 6844134
    Abstract: A photosensitive polymer comprises a fluorinated ethylene glycol group and a chemically amplified resist composition including the photosensitive polymer. The photosensitive polymer has a weight average molecular weight of about 3,000-50,000 having a repeating unit as follows: wherein R1 is a hydrogen atom or methyl group, and R2 is a fluorinated ethylene glycol group having 3 to 10 carbon atoms.
    Type: Grant
    Filed: November 5, 2002
    Date of Patent: January 18, 2005
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Sang-Jun Choi, Joo-Tae Moon, Sang-Gyun Woo, Kwang-Sub Yoon, Ki-Yong Song
  • Patent number: 6844403
    Abstract: The present invention provides a cyclic olefin addition copolymer which has a reactive silyl group having a specific structure, excels in optical transparency, heat resistance, and adhesion, and is capable of producing a crosslinked product having improved dimensional stability, solvent resistance, and chemical resistance. The present invention also provides a process for producing the cyclic olefin addition copolymer, a crosslinking composition, a crosslinked product and a process for producing the same, and an optically transparent material (transparent resin film) comprising the cyclic olefin addition copolymer. The optically transparent material excels in optical transparency and heat resistance, exhibits improved dimensional stability, adhesion, solvent resistance, and chemical resistance, and is capable of improving fragility and preventing occurrence of cracks in the film.
    Type: Grant
    Filed: September 12, 2002
    Date of Patent: January 18, 2005
    Assignee: JSR Corporation
    Inventors: Noboru Oshima, Yooichiroh Maruyama, Michitaka Kaizu, Katsutoshi Sawada, Toshihiro Hayashi, Kenzo Ohkita
  • Patent number: 6838489
    Abstract: The invention provides a method for converting a less active or slower to initiate system to a higher activity system so that at the end of a polymerization the most active species is present in the system. The invention generally relates to a process for converting a less active or slower to initiate catalyst system to a higher activity catalyst system wherein the process comprises contacting a protected N-heterocyclic carbene with a metathesis catalyst and an olefin in the presence of energy. One of the benefits of the invention is that the amount of catalyst required is less than or lowered in the presence of the protected N-heterocyclic carbene as compared to the amount of catalyst required in the absence of the protected N-heterocyclic carbene. The protected N-heterocyclic carbene can be unsaturated or saturated. In addition, the invention describes novel ruthenium initiators and methods of making the same.
    Type: Grant
    Filed: March 25, 2002
    Date of Patent: January 4, 2005
    Assignees: Cymetech, LLC, California Institute of Technology
    Inventors: Andrew Bell, Robert H. Grubbs, John P Morgan, Jason L. Moore
  • Patent number: 6835529
    Abstract: A polymer having a repeating unit comprising a copolymer of butadiene sulfone and maleic anhydride, and a chemically amplified resist composition comprising the polymer. The resist composition includes a photosensitive polymer having a first repeating unit comprising a copolymer of butadiene sulfone and maleic anhydride, the first repeating unit represented by a formula: and a second repeating unit copolymerized with the first repeating unit.
    Type: Grant
    Filed: March 11, 2003
    Date of Patent: December 28, 2004
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Sang-jun Choi, Woo-sung Han, Sang-gyun Woo
  • Patent number: 6835525
    Abstract: A novel polymer is obtained by copolymerizing a (meth)acrylic acid derivative with a vinyl ether compound, an allyl ether compound and an oxygen-containing alicyclic olefin compound. A resist composition comprising the polymer as a base resin is sensitive to high-energy radiation, has excellent sensitivity, resolution, etching resistance, and minimized swell and lends itself to micropatterning with electron beams or deep-UV.
    Type: Grant
    Filed: February 13, 2002
    Date of Patent: December 28, 2004
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Tsunehiro Nishi, Mutsuo Nakashima, Seiichiro Tachibana, Kenji Funatsu
  • Patent number: 6824955
    Abstract: A resist composition comprising a copolymer of an acrylic ester monomer containing fluorine at &agr;-position with a norbornene derivative containing oxygen or sulfur within the norbornene ring as a base resin is sensitive to high-nergy radiation below 200 nm, has excellent sensitivity, transparency and dry etching resistance, and is suited for lithographic microprocessing.
    Type: Grant
    Filed: December 26, 2002
    Date of Patent: November 30, 2004
    Assignees: 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
  • Patent number: 6825307
    Abstract: Methods for the addition polymerization of cycloolefins using a cationic Group 10 metal complex and a weakly coordinating anion of the formula: [(R′)zM(L′)x(L″)y]b[WCA]d wherein [(R′)zM(L′)x(L″)y] is a cation complex where M represents a Group 10 transition metal; R′ represents an anionic hydrocarbyl containing ligand; L′ represents a Group 15 neutral electron donor ligand; L″ represents a labile neutral electron donor ligand; x is 1 or 2; and y is 0, 1, 2, or 3; and z is 0 or 1, wherein the sum of x, y, and z is 4; and [WCA] represents a weakly coordinating counteranion complex; and b and d are numbers representing the number of times the cation complex and weakly coordinating counteranion complex are taken to balance the electronic charge on the overall catalyst complex.
    Type: Grant
    Filed: July 16, 2002
    Date of Patent: November 30, 2004
    Assignee: Promerus, LLC
    Inventor: Brian L. Goodall
  • Patent number: 6818285
    Abstract: A crosslinked polyarylene material with a reduced coefficient of thermal expansion at high temperatures compared with conventional crosslinked polyarylene materials is provided. In addition, an integrated circuit article containing a crosslinked polyarylene polymer with reduced coefficient of thermal expansion at high temperatures is provided.
    Type: Grant
    Filed: December 31, 2002
    Date of Patent: November 16, 2004
    Assignee: International Business Machines Corporation
    Inventors: Jeffrey C. Hedrick, Muthumanickam Sankarapandian, Christy S. Tyberg, James P. Godschalx, Qingshan J. Niu, Harry C. Silvis
  • Patent number: 6818376
    Abstract: The present invention provides a cross-linker monomer of formula 1, a photoresist polymer derived from a monomer comprising the same, and a photoresist composition comprising the photoresist polymer. The cross-linking unit of the photoresist polymer can be hydrolyzed (or degraded or broken) by an acid generated from a photoacid generator on the exposed region. It is believed that this acid degradation of the cross-linking unit increases the contrast ratio between the exposed region and the unexposed region. The photoresist composition of the present invention has improved pattern profile, enhanced adhesiveness, excellent resolution, sensitivity, durability and reproducibility. where A, B, R1, R2, R3, R4, R5, R6 and k are as defined herein.
    Type: Grant
    Filed: April 9, 2002
    Date of Patent: November 16, 2004
    Assignee: Hynix Semiconductor Inc.
    Inventors: Geun Su Lee, Jae Chang Jung, Ki Ho Baik
  • Patent number: RE38676
    Abstract: The present invention generally relates to the use of certain ruthenium and osmium complexes that are substantially inactive at a first temperature (preferably about room temperature) but becomes progressively more active at a higher second temperature. This difference in reactivities allows the reaction mixture to be formed and manipulated at the first temperature until polymerization is desired. When appropriate, the reaction mixture is heated to a suitable temperature (preferably greater than 50° C.) to activate the catalyst and to initiate polymerization. Because both the initiation and the rate of polymerization may be controlled with temperature, the inventive methods are especially suitable for ring opening metathesis polymerization (“ROMP”) reactions and for molding polymer articles that require extended pot-lives.
    Type: Grant
    Filed: August 21, 2002
    Date of Patent: December 21, 2004
    Assignee: California Institute of Technology
    Inventors: Robert H. Grubbs, Thomas E. Wilhelm