5-membered Heterocyclic Ring Compound Contains At Least One Oxygen Atom Patents (Class 526/270)
  • Patent number: 9505778
    Abstract: Disclosed herein are monomers formed by reacting a sugar derived compound(s) comprising a lactone and two hydroxyls with a compound(s) comprising an isocyanate and an acrylate or methacrylate. Polymers formed from such monomers, and articles formed from the polymers are also disclosed.
    Type: Grant
    Filed: November 26, 2014
    Date of Patent: November 29, 2016
    Assignee: REGENTS OF THE UNIVERSITY OF MINNESOTA
    Inventors: James Gallagher, Theresa Reineke, Marc A. Hillmyer
  • Patent number: 9493685
    Abstract: Pre-treatment composition and printing method for printing durable images using such pre-treatment composition are disclosed. A disclosed example of the pre-treatment composition includes a liquid vehicle, a polyvalent metal salt, a latex resin and thickener. Moreover, a printing method is also disclosed with an ink composition comprising of an aqueous liquid vehicle and a colorant after pre-treatment with said pre-treatment composition.
    Type: Grant
    Filed: February 23, 2011
    Date of Patent: November 15, 2016
    Assignee: Hewlett-Packard Development Company, L.P.
    Inventors: George Sarkisian, Ali Emamjomeh, Elizabeth Ann Visnyak
  • Patent number: 9309332
    Abstract: The invention provides novel polymer compositions and methods for preparing such compositions. The invention also provides methods for polymerizing various unsaturated monomers, including naturally occurring or plant biomass-derived renewable acrylic monomers. The monomers can be rapidly polymerized using various organic catalysts or organometallic catalysts, as described herein. In one embodiment, nearly perfectly isotactic polymers (mmmm>99%) can be prepared using a C2-symmetric zirconocenium catalyst.
    Type: Grant
    Filed: August 26, 2013
    Date of Patent: April 12, 2016
    Assignee: Colorado State University Research Foundation
    Inventors: Eugene Y. Chen, Yangjian Hu, Yuetao Zhang
  • Publication number: 20150147696
    Abstract: Provided is a method for producing a polymer compound that has very low contents of impurities such as metal components and exhibits excellent storage stability. The production method gives such a polymer compound. The polymer compound is incorporated into a photoresist resin composition. The method for producing a polymer compound includes the step of filtering a resin solution containing a polymer compound through a filter. The filter is approximately devoid of strongly acidic cation-exchange groups and develops a positive zeta potential. The polymer compound includes a monomer unit (a) and a monomer unit (b). The monomer unit (a) includes at least one monomer units represented by Formulae (a1) to (a3). The monomer unit (b) contains a group capable of releasing a moiety thereof by the action of an acid to develop solubility in an alkali.
    Type: Application
    Filed: July 26, 2013
    Publication date: May 28, 2015
    Applicant: DAICEL CORPORATION
    Inventors: Akira Eguchi, Masamichi Nishimura
  • Publication number: 20150147697
    Abstract: A resist composition comprising a polymer comprising recurring units (a) of formula (1) and having a Mw of 1,000-500,000 as base resin is provided. R1 is H or methyl, X is a single bond or —C(?O)—O—R5—, R2 is a single bond or C1-C4 alkylene, R3 is C2-C8 alkylene, R4 is an acid labile group, R5 is a single bond or C1-C4 alkylene, and 0<a?1.0. The composition is of dual-tone type in that an intermediate dose region of resist film is dissolved in a developer, but unexposed and over-exposed regions of resist film are insoluble.
    Type: Application
    Filed: November 25, 2014
    Publication date: May 28, 2015
    Applicant: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Jun Hatakeyama, Masayoshi Sagehashi
  • Publication number: 20150148507
    Abstract: Disclosed herein are monomers formed by reacting a sugar derived compound(s) comprising a lactone and two hydroxyls with a compound(s) comprising an isocyanate and an acrylate or methacrylate. Polymers formed from such monomers, and articles formed from the polymers are also disclosed.
    Type: Application
    Filed: November 26, 2014
    Publication date: May 28, 2015
    Inventors: James Gallagher, Theresa Reineke, Marc A. Hillmyer
  • Publication number: 20150140484
    Abstract: There is provided an actinic ray-sensitive or radiation-sensitive resin composition comprising: (A) a resin containing a repeating unit represented by the first specific formula and a repeating unit represented by the second specific formula, wherein the content of the repeating unit represented by the first specific formula is 35 mol % or more based on all repeating units in the resin (A), a resist film formed using the actinic ray-sensitive or radiation-sensitive resin composition.
    Type: Application
    Filed: January 26, 2015
    Publication date: May 21, 2015
    Applicant: FUJIFILM CORPORATION
    Inventors: Hiroo TAKIZAWA, Shuji HIRANO, Natsumi YOKOKAWA, Wataru NIHASHI
  • Publication number: 20150140497
    Abstract: A resist composition which generates acid upon exposure and exhibits changed solubility in a developing solution under action of acid, and which includes a base component (A) which exhibits changed solubility in a developing solution under action of acid, the base component (A) including a polymeric compound (A1) having a structural unit (a0) represented by general formula (a0-0) shown below (wherein V11 represents an aliphatic cyclic group with or without a substituent; R1 represents a lactam-containing cyclic group or a sultam-containing cyclic group; Y1 represents an oxygen atom (—O—), an ester bond (—C(?O)—O—) or a single bond; and W2 represents a group formed by a polymerization reaction of a polymerizable group-containing group).
    Type: Application
    Filed: November 13, 2014
    Publication date: May 21, 2015
    Inventors: Masatoshi Arai, Yoshiyuki Utsumi
  • Publication number: 20150132687
    Abstract: There is provided an actinic ray-sensitive or radiation-sensitive resin composition comprising (P) a resin containing a repeating unit represented by the specific formula (1) and a repeating unit represented by the specific formula (A); a resist film formed using the actinic ray-sensitive or radiation-sensitive resin composition; a pattern forming method comprising (i) a step of forming a film from the actinic ray-sensitive or radiation-sensitive resin composition, (ii) a step of exposing the film, and (iii) a step of developing the exposed film by using a developer to form a pattern; a method for manufacturing an electronic device, comprising the pattern forming method, and an electronic device manufactured by the manufacturing method of an electronic device.
    Type: Application
    Filed: January 26, 2015
    Publication date: May 14, 2015
    Applicant: FUJIFILM CORPORATION
    Inventors: Shuji HIRANO, Natsumi YOKOKAWA, Hiroo TAKIZAWA, Wataru NIHASHI
  • Publication number: 20150132688
    Abstract: There is provided an actinic ray-sensitive or radiation-sensitive resin composition comprising (P) a resin having (a) a repeating unit represented by the specific formula; a resist film formed using the actinic ray-sensitive or radiation-sensitive resin composition; a pattern forming method comprising (i) a step of forming a film by using the actinic ray-sensitive or radiation-sensitive resin composition, (ii) a step of exposing the film, and (iii) a step of developing the exposed film by using a developer to form a pattern; a method for manufacturing an electronic device, comprising the pattern forming method; and an electronic device manufactured by the manufacturing method of an electronic device.
    Type: Application
    Filed: January 26, 2015
    Publication date: May 14, 2015
    Applicant: FUJIFILM Corporation
    Inventors: Natsumi YOKOKAWA, Shuji HIRANO, Hiroo TAKIZAWA, Wataru NIHASHI
  • Publication number: 20150132698
    Abstract: A resin containing a structural unit derived from a compound represented by the formula (aa) wherein T, R1 and Z1 are defined in the specification.
    Type: Application
    Filed: January 23, 2015
    Publication date: May 14, 2015
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Koji ICHIKAWA, Yusuke FUJI, Satoshi YAMAGUCHI
  • Publication number: 20150119524
    Abstract: Provided is an antifoaming agent for a coating agent, which suppresses foaming of a coating agent by being blended into a nonaqueous agent in a small amount, thereby improving pinhole preventing performance, and which may form a thermo-setting coating film or a thermo-drying coating film having an excellent aesthetic appearance by suppressing the generation of pinholes without deteriorating smoothing performance of the coating film even under conditions where pinholes are easily generated.
    Type: Application
    Filed: April 25, 2013
    Publication date: April 30, 2015
    Applicant: KYOEISHA CHEMICAL CO., LTD.
    Inventors: Daisuke Mitomi, Yuusuke Sainouchi, Yousuke Kataoka
  • Publication number: 20150084031
    Abstract: A polymerizable monomer represented by the following formula (1) wherein at least one of Ar1 to Ar3 is substituted by a group represented by the following formula (2) and which is substituted by one or more groups comprising a polymerizable functional group. Ar1 to Ar3 are a substituted or unsubstituted aryl group having 6 to 40 ring carbon atoms, Ar6 is a substituted or unsubstituted aryl group having 6 to 40 ring carbon atoms and Ar4 and Ar5 are a substituted or unsubstituted arylene group having 6 to 40 ring carbon atoms.
    Type: Application
    Filed: December 2, 2014
    Publication date: March 26, 2015
    Inventors: Mitsuru EIDA, Nobohiro YABUNOUCHI, Yumiko MIZUKI, Masami WATANABE, Akinori YOMOGITA
  • Publication number: 20150086912
    Abstract: There is provided an actinic ray-sensitive or radiation-sensitive resin composition comprising (P) a resin having a repeating unit (A) represented by the specific formula (I) capable of generating an acid on the side chain of the resin upon irradiation with an actinic ray or radiation, and a resist film formed with the actinic ray-sensitive or radiation-sensitive resin composition, and a pattern forming method comprising: exposing the resist film, and developing the exposed resist film, and a method for manufacturing a semiconductor device, containing the pattern forming method, and a semiconductor device manufactured by the manufacturing method of the semiconductor device.
    Type: Application
    Filed: November 26, 2014
    Publication date: March 26, 2015
    Applicant: FUJIFILM CORPORATION
    Inventors: Takeshi KAWABATA, Hideaki TSUBAKI, Hiroo TAKIZAWA, Natsumi YOKOKAWA
  • Publication number: 20150064622
    Abstract: A compound represented by formula (I): wherein R1 represents a hydrogen atom, a halogen atom, or a C1-C6 alkyl group which may have a halogen atom; R2 and R3 each independently represent a hydrogen atom or a C1-C6 monovalent saturated hydrocarbon group, and R4 represents a C1-C6 monovalent saturated linear hydrocarbon group, a C3-C6 monovalent saturated branched hydrocarbon group, a C5-C12 monovalent alicyclic hydrocarbon group or a C5-C12 monovalent alicyclic hydrocarbon-containing group, or R3 and R4 represent a C2-C6 heterocyclic ring together with an oxygen atom and a carbon atom; A1 represents a single bond, or *-A2-X1-(A3-X2)a— where A2 and A3 each independently represent a C1-C6 alkanediyl group, X1 and X2 each independently represent an oxygen atom, a carbonyloxy group or an oxycarbonyl group, and “a” represents 0 or 1; A4 represents a C1-C6 alkanediyl group; Ad represents a divalent adamantanediyl group.
    Type: Application
    Filed: September 2, 2014
    Publication date: March 5, 2015
    Inventors: Isao YOSHIDA, Koji ICHIKAWA
  • Publication number: 20150064626
    Abstract: A positive resist composition is provided comprising a polymer comprising recurring units having a carboxyl and/or phenolic hydroxyl group substituted with an acid labile group and recurring units of tert-butyl or tert-amyl-substituted hydroxyphenyl methacrylate and having a weight average molecular weight of 1,000-500,000. The resist composition has a satisfactory effect of suppressing acid diffusion and a high resolution, and forms a pattern of good profile and minimal edge roughness after exposure.
    Type: Application
    Filed: July 14, 2014
    Publication date: March 5, 2015
    Applicant: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Jun Hatakeyama, Koji Hasegawa
  • Publication number: 20150056555
    Abstract: A system and method for depositing a photoresist and utilizing the photoresist are provided. In an embodiment a deposition chamber is utilized along with a first precursor material comprising carbon-carbon double bonds and a second precursor material comprising repeating units to deposit the photoresist onto a substrate. The first precursor material is turned into a plasma in a remote plasma chamber prior to being introduced into the deposition chamber. The resulting photoresist comprises a carbon backbone with carbon-carbon double bonds.
    Type: Application
    Filed: August 22, 2013
    Publication date: February 26, 2015
    Applicant: Taiwan Semiconductor Manufacturing Company, Ltd.
    Inventors: Keng-Chu Lin, Joung-Wei Liou, Cheng-Han Wu, Ya Hui Chang
  • Publication number: 20150044608
    Abstract: [Object] Provided is a method of manufacturing a polymer for lithography having reduced residual amounts of un-reacted monomers and a poor solvent used for a purification process. [Solving Means] The method of manufacturing a polymer for lithography includes a polymerization process of obtaining a polymerization reaction solution including a polymer by polymerizing monomers in the presence of a polymerization solvent, and a purification process of obtaining a wet powder of a purified polymer by purifying the polymer in the polymerization reaction solution using a re-precipitation method, in which the purification process includes a process of filtering at a filtration differential pressure of 50 kPa or more, and the solid content of the wet powder of the purified polymer exceeds 40% by mass and is less than 65% by mass.
    Type: Application
    Filed: August 6, 2014
    Publication date: February 12, 2015
    Applicant: Mitsubishi Rayon Co., Ltd.
    Inventors: Atsushi YASUDA, Kazuaki MUKAI
  • Publication number: 20150037734
    Abstract: A resist composition containing a compound represented by general formula (m0), wherein R1 and R2 each independently represents an aryl group which may have a substituent, an alkyl group which may have a substituent, or an alkenyl group which may have a substituent, provided that R1 and R2 may be mutually bonded to form a ring with the sulfur atom; R3 represents an aromatic hydrocarbon group which may have a substituent, an alkenyl group which may have a substituent, or an alkynyl group which may have a substituent; V1 represents a single bond or an alkylene group, provided that, when R3 is an aromatic hydrocarbon group which may have a substituent, V1 is an alkylene group; and X0? represents a monovalent organic anion.
    Type: Application
    Filed: July 23, 2014
    Publication date: February 5, 2015
    Inventors: Takashi Nagamine, Yoshitaka Komuro, Masatoshi Arai, Yoshiyuki Utsumi
  • Publication number: 20150034871
    Abstract: An object is to provide a polymerizable compound having high polymerization reactivity, a high conversion ratio and high solubility in a liquid crystal composition, a polymerizable composition containing the compound, a liquid crystal composite prepared from the composition, and a liquid crystal display device having the composite. A solution is a polymerizable compound represented by formula (1). In the formula, for example, P1 and P2 are —OCO—(CH3)C?CH2; S1 and S2 are a single bond; ring A1, ring A2 and ring A3 are 1,4-phenylene; Z1, Z2 and Z3 are a single bond; two of G is —CH? or —N?; and a is 0 or 1.
    Type: Application
    Filed: July 31, 2014
    Publication date: February 5, 2015
    Applicants: JNC PETROCHEMICAL CORPORATION, JNC CORPORATION
    Inventors: Yasuyuki GOTOH, Teizi SATOU
  • Publication number: 20150017586
    Abstract: A positive resist composition is provided comprising a polymer comprising recurring units having a carboxyl or phenolic hydroxyl group substituted with an acid labile group and recurring units of hydroxyanthraquinone or hydroxy-2,3-dihydro-1,4-anthracenedione methacrylate, and having a Mw of 1,000-500,000. The resist composition has a satisfactory effect of suppressing acid diffusion and a high resolution, and forms a pattern of good profile and minimal edge roughness after exposure.
    Type: Application
    Filed: July 3, 2014
    Publication date: January 15, 2015
    Applicant: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Jun Hatakeyama, Masayoshi Sagehashi
  • Publication number: 20140371413
    Abstract: The present invention provides a chemical sealing film which has high chemical resistance and high breaking strength and which does not contain chlorine. The present invention relates to a chemical sealing film containing an organic compound represented by general formula (1) shown in Claim 1. In general formula (1), R is a linear alkylene group having carbon atoms of 5 or more and 10 or less and n is an integer of 10 or more and 480 or less.
    Type: Application
    Filed: December 26, 2012
    Publication date: December 18, 2014
    Applicant: CANON KABUSHIKI KAISHA
    Inventors: Toshinari Miura, Katsuhiro Matsuda, Takeshi Komuro, Kie Yutaka
  • Publication number: 20140371412
    Abstract: Provided is a resist copolymer which has favorable sensitivity, enables a resist pattern to be formed to have a favorable shape, has favorable dry etching resistance when a dry etching is carried out using the resist pattern as a mask, and suppresses the surface roughness of a pattern formed by carrying out a dry etching process to a substrate. A resist copolymer including a constituent unit (1) based on a (meth)acrylic acid ester derivative having a cyclic hydrocarbon group such as an adamantane ring and two or more cyano groups bonded to the cyclic hydrocarbon group, a constituent unit (2) having a lactone backbone and a cross-linking cyclic structure, and a constituent unit (3) having an acid leaving group.
    Type: Application
    Filed: June 10, 2014
    Publication date: December 18, 2014
    Applicant: Mitsubishi Rayon Co., Ltd.
    Inventors: Keisuke KATO, Atsushi YASUDA, Ryuichi ANSAI, Shinichi MAEDA
  • Publication number: 20140363772
    Abstract: A resist composition including a high-molecular weight compound having a constituent unit represented by general formula (a0-1), a constituent unit (a1) containing a group containing a monocyclic group or a chain group among acid decomposable groups whose polarity increases by action of acid, a constituent unit (a1?) containing a group containing a polycyclic group among acid decomposable groups whose polarity increases by the action of an acid, and a constituent unit (a2) containing a lactone-containing monocyclic group, with a proportion of the constituent unit (a1) being equal to a proportion of the constituent unit (a1?) or more; and a method for forming a resist pattern using the resist composition.
    Type: Application
    Filed: May 29, 2014
    Publication date: December 11, 2014
    Applicant: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Junichi Tsuchiya, Yuta Iwasawa
  • Publication number: 20140308614
    Abstract: A negative pattern is formed by applying a resist composition onto a substrate, prebaking, exposing to high-energy radiation, PEB, and developing the exposed resist film in an organic solvent developer to dissolve the unexposed region of resist film. The resist composition is based on a polymer comprising recurring units (a1) of formula (1) wherein R1 is H or CH3, R2 and R3 are H, F or a monovalent hydrocarbon group, R4 is H or a monovalent hydrocarbon group, R5 and R6 are a monovalent hydrocarbon group, X1 is a divalent hydrocarbon group, and k1=0 or 1. A fine hole or trench pattern can be formed therefrom.
    Type: Application
    Filed: March 14, 2014
    Publication date: October 16, 2014
    Applicant: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Koji Hasegawa, Masayoshi Sagehashi, Tomohiro Kobayashi, Kazuhiro Katayama
  • Patent number: 8859180
    Abstract: [Task to Be Achieved] To provide a chemically amplified type positive copolymer for semiconductor lithography, which has eliminated the problems of prior art, has a high development contrast, and has excellent resolution in fine-pattern formation; a composition for semiconductor lithography which contains the copolymer; and a process for producing the copolymer. [Means for Achievement] The copolymer for semiconductor lithography according to the present invention is a copolymer which has at least (A) a repeating unit having a structure which has an alkali-soluble group protected by an acid-labile, dissolution-suppressing group, (B) a repeating group having a lactone structure and (C) a repeating group having an alcoholic hydroxyl group and which is characterized by having an acid value of 0.01 mmol/g or less as determined by dissolving the copolymer in a solvent and subjecting the solution to neutralization titration with a solution of an alkali metal hydroxide using Bromothymol Blue as an indicator.
    Type: Grant
    Filed: October 19, 2007
    Date of Patent: October 14, 2014
    Assignee: Maruzen Petrochemical Co., Ltd.
    Inventors: Tomo Oikawa, Takayoshi Okada, Masaaki Kudo, Takanori Yamagishi
  • Patent number: 8846817
    Abstract: An ionic polymer of formula VI wherein each b=0 or 1; X is hydrogen, 1/z of a metal ion of charge z, a protonated nitrogen base, or a tetrasubstituted organic ammonium compound; the molar ratio of q:r:s:t=(100-0.1):(0-99.9):(0-50):(0-30); R1, R2 and R3 are hydrogen or C1-4 alkyl; R4, R5, R6 and R7 are hydrogen, C1-4 alkyl or F, wherein F is a functional group that imparts a property to polymer VI, at least one and no more than two of R4, R5, R6 and R7 are F and F is the same or different; G is a single bond or a C1-30 hydrocarbyl group; and for each instance of t when t is not zero, c=0-5 and d=0-5, provided that c+d=1-5, and wherein q, r and s as present in c are independent of any other value of q, r and s.
    Type: Grant
    Filed: November 11, 2011
    Date of Patent: September 30, 2014
    Assignee: Segetis, Inc.
    Inventors: Dorie J. Yontz, Brian D. Mullen, Cora M. Leibig, Marc D. Rodwogin, Vivek Badarinarayana, Feng Jing, Friederike T. Stollmaier
  • Publication number: 20140287362
    Abstract: A resist composition which generates an acid upon exposure and exhibits changed solubility in a developing solution by the action of the acid contains a high-molecular weight compound (A1) having a constituent unit (a0) represented by a general formula (a0-1) and a constituent unit (a1-1) including a monocyclic group-containing acid decomposable group whose polarity increases by the action of an acid. In the formula (a0-1), R represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a halogenated alkyl group having 1 to 5 carbon atoms; Ya01 represents a single bond or a divalent linking group; X01 represents a sulfur atom or an oxygen atom; and Ra01 represents an optionally substituted cyclic group, chain alkyl group, or chain alkenyl group.
    Type: Application
    Filed: March 19, 2014
    Publication date: September 25, 2014
    Applicant: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Tsuyoshi Nakamura, Kazuishi Tanno, Naoto Motoike, Junichi Tsuchiya, Yoichi Hori
  • Publication number: 20140288230
    Abstract: The present invention provides methylene beta-ketoester monomers, methods for producing the same, and compositions and products formed therefrom. In the method for producing the methylene beta-ketoesters of the invention, a beta-ketoester is reacted with a source of formaldehyde in a modified Knoevenagel reaction optionally in the presence of an acidic or basic catalyst, and optionally in the presence of an acidic or non-acidic solvent, to form reaction complex. The reaction complex may be an oligomeric complex. The reaction complex is subjected to further processing, which may be vaporization by contact with an energy transfer means in order to isolate the beta-ketoester monomer. The present invention further compositions and products formed from methylene beta-ketoester monomers of the invention, including monomer-based products (e.g., inks, adhesives, coatings, sealants or reactive molding) and polymer-based products (e.g., fibers, films, sheets, medical polymers, composite polymers and surfactants).
    Type: Application
    Filed: October 18, 2012
    Publication date: September 25, 2014
    Inventors: Bernard M. Malofsky, Adam G. Malofsky, Tanmoy Dey
  • Publication number: 20140242519
    Abstract: A polymer for resist use is obtainable from a monomer having formula (1) wherein R1 is H, CH3 or CF3, R2 and R3 are a monovalent hydrocarbon group, R4 to R9 are hydrogen or a monovalent hydrocarbon group, R10 is a monovalent hydrocarbon group or fluorinated hydrocarbon group, A1 is a divalent hydrocarbon group, k1 is 0 or 1, and n1A is 0, 1 or 2. A resist composition comprising the polymer displays a high dissolution contrast during organic solvent development.
    Type: Application
    Filed: February 3, 2014
    Publication date: August 28, 2014
    Applicant: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Masayoshi Sagehashi, Koji Hasegawa, Kazuhiro Katayama
  • Patent number: 8808966
    Abstract: A positive resist composition comprising a polymer having carboxyl groups substituted with an acid labile group having formula (1) exhibits a high contrast of alkaline dissolution rate before and after exposure, a high resolution, a good pattern profile and minimal edge roughness. In formula (1), A is —(CR22)m—, B is —(CR52)n—, R2 and R5 are hydrogen or alkyl, m and n are 1 or 2, R3 is alkyl, alkenyl, alkynyl or aryl, R6 is alkyl, alkoxy, alkanoyl, alkoxycarbonyl, hydroxyl, nitro, aryl, halogen, or cyano, and p is 0 to 4.
    Type: Grant
    Filed: July 25, 2012
    Date of Patent: August 19, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Koji Hasegawa
  • Patent number: 8802798
    Abstract: A photoresist material for lithography using a light of 220 nm or less which comprises at least a polymer represented by the following formula (2) and a photo-acid generator for generating an acid by exposure: wherein R1, R2, R3 and R5 are each a hydrogen atom or a methyl group; R4 is an acid-labile group or one of a specified subset of alicyclic hydrocarbon groups, alicyclic hydrocarbon groups, or hydrocarbon groups; R6 is a hydrogen atom or one of a specified subset of hydrocarbon groups or alicyclic hydrocarbon groups; x, y and z are optional values which meet x+y+z=1, 0<x?1, 0?y<1 and 0?z<1. Also disclosed is a resin having a (meth)acrylate unit of an alicyclic lactone structure represented by the formula (3): wherein R8 is a hydrogen atom or a methyl group, and R9 is one of a specified subset of hydrocarbon groups.
    Type: Grant
    Filed: August 29, 2008
    Date of Patent: August 12, 2014
    Assignee: NEC Corporation
    Inventors: Katsumi Maeda, Shigeyuki Iwasa, Kaichiro Nakano, Etsuo Hasegawa
  • Patent number: 8795946
    Abstract: Polymerizable ester compounds having formula (1) are novel wherein R1 is H, F, methyl or trifluoromethyl, R2 is an acid labile group, Aa is a divalent hydrocarbon group which may be separated by —O— or —C(?O)—, and k1 is 0 or 1. They are useful as monomers to produce polymers which are transparent to radiation ?500 nm. Radiation-sensitive resist compositions comprising the polymers as base resin exhibit excellent developed properties.
    Type: Grant
    Filed: July 13, 2012
    Date of Patent: August 5, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Koji Hasegawa, Masayoshi Sagehashi, Yuuki Suka, Masashi Ilo
  • Publication number: 20140212813
    Abstract: A radiation-sensitive resin composition includes a first polymer including an acid-labile group, an acid generator to generate an acid upon exposure to radiation, and a second polymer including a fluorine atom and a functional group shown by a general formula (x). The second polymer has a fluorine atom content higher than a fluorine atom content of the first polymer. R1 represents an alkali-labile group. A represents an oxygen atom, —NR?—, —CO—O—# or —SO2—O—##, wherein the oxygen atom represented by A is not an oxygen atom bonded directly to an aromatic ring, a carbonyl group, or a sulfoxyl group, R? represents a hydrogen atom or an alkali-labile group, and “#” and “##” each indicate a bonding hand bonded to R1.
    Type: Application
    Filed: April 2, 2014
    Publication date: July 31, 2014
    Applicant: JSR CORPORATION
    Inventors: Yuusuke ASANO, Mitsuo SATOU, Hiromitsu NAKASHIMA, Kazuki KASAHARA, Yoshifumi OIZUMI, Masafumi HORI, Takanori KAWAKAMI, Yasuhiko MATSUDA, Kazuo NAKAHARA
  • Publication number: 20140206829
    Abstract: The present invention provides novel bimetallic complexes and methods of using the same in the isoselective polymerization of epoxides. The invention also provides methods of kinetic resolution of epoxides. The invention further provides polyethers with high enantiomeric excess that are useful in applications ranging from consumer goods to materials.
    Type: Application
    Filed: March 21, 2014
    Publication date: July 24, 2014
    Applicant: Cornell University
    Inventors: Geoffrey W. Coates, Wataru Hirahata
  • Publication number: 20140199631
    Abstract: A polymer for resist use is obtainable from a monomer having formula (1) wherein R1 is H, CH3 or CF3 and R2 is H or an acid labile group. A resist composition comprising the polymer displays a high sensitivity and a high dissolution contrast during both alkaline development and organic solvent development.
    Type: Application
    Filed: December 17, 2013
    Publication date: July 17, 2014
    Applicant: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Masayoshi Sagehashi, Koji Hasegawa, Kazuhiro Katayama
  • Patent number: 8771917
    Abstract: Provided are (meth)acrylate monomers containing acetal moieties, polymers containing a unit formed from such a monomer and photoresist compositions containing such a polymer. The monomers, polymers and photoresist compositions are useful in forming photolithographic patterns. Also provided are substrates coated with the photoresist compositions, methods of forming photolithographic patterns and electronic devices. The compositions, methods and coated substrates find particular applicability in the manufacture of semiconductor devices.
    Type: Grant
    Filed: December 31, 2011
    Date of Patent: July 8, 2014
    Assignees: Rohm and Haas Electronics Materials LLC, Dow Global Technologies LLC
    Inventors: Matthias S. Ober, Young Cheol Bae, Yi Liu, Seung-Hyun Lee, Jong Keun Park
  • Publication number: 20140178820
    Abstract: An additive polymer comprising recurring styrene units having an ester group bonded to a CF3—C(OR2)—R3 group (wherein R2 is H, acyl or acid labile group, R3 is H, CH3 or CF3) such as 1,1,1,3,3,3-hexafluoro-2-propanol is added to a polymer capable of increasing alkali solubility under the action of acid to formulate a resist composition. The resist composition can minimize outgassing from a resist film during the EUV lithography and form a resist film having a hydrophilic surface sufficient to prevent formation of blob defects on the film after development.
    Type: Application
    Filed: December 9, 2013
    Publication date: June 26, 2014
    Applicant: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Jun Hatakeyama, Koji Hasegawa, Kenji Funatsu
  • Patent number: 8754172
    Abstract: An adhesive composition includes an acrylic copolymer having at least one alkyl group, at least one hydroxyl group, and at least one furyl based group; and a curing agent.
    Type: Grant
    Filed: February 15, 2011
    Date of Patent: June 17, 2014
    Assignee: Cheil Industries, Inc.
    Inventors: Kyoung Jin Ha, Irina Nam, Lee Jun Kim, Kil Sung Lee, Eun Hwan Jeong, Woo Jin Jeong
  • Publication number: 20140163127
    Abstract: The present disclosure relates to the preparation of acrylate, alkacrylate, allyl, and polycarbonate derivatives of hydroxy ketal esters, and uses thereof.
    Type: Application
    Filed: November 1, 2013
    Publication date: June 12, 2014
    Applicant: SEGETIS, INC.
    Inventors: Sergey SELIFONOV, Brian Daniel MULLEN, Douglas Alan WICKS, Vivek BADARINARAYANA
  • Publication number: 20140142267
    Abstract: A toner for electrostatic image development having sufficient low-temperature fixing properties, and excellent heat resistant storage stability and crush resistance is provided. In toner particles containing at least a binder resin, the binder resin contains a polymer having a structural unit represented by a general formula (1), wherein R1, R2, and R3 each independently represent a hydrogen atom, a hydroxyl group, or an alkoxy group, or two adjacent groups of R1, R2, and R3 combine to form —O(CH2)iO—, where i represents an integer of 1 or 2, provided that at least one of R1, R2, and R3 is an alkoxy group, or two adjacent groups combine to form —O(CH2)iO—; and R4 represents a hydrogen atom, a halogen atom, an alkyl group, a hydroxyl group, or an alkoxy group.
    Type: Application
    Filed: October 25, 2013
    Publication date: May 22, 2014
    Applicant: Konica Minolta, Inc.
    Inventors: Kazuyoshi GOAN, Mikio KOUYAMA, Hajime TADOKORO
  • Publication number: 20140141373
    Abstract: A compound represented by formula (I). In the formula, R1 represents a hydrocarbon group of 1 to 10 carbon atoms; Z represents a hydrocarbon group of 1 to 10 carbon atoms or a cyano group; provided that R1 and Z may be mutually bonded to form a ring; X represents a divalent linking group having any one selected from —O—C(?O)—, —NH—C(?O)— and —NH—C(?NH)— on a terminal that comes into contact with Q; p represents an integer of 1 to 3; Q represents a hydrocarbon group having a valency of (p+1), provided that, when p is 1, Q may be a single bond; R2 represents a single bond, an alkylene group which may have a substituent or an arylene group which may have a substituent; q represents 0 or 1; r represents an integer of 0 to 8; and A+ represents a metal cation or an organic cation.
    Type: Application
    Filed: June 15, 2012
    Publication date: May 22, 2014
    Applicant: TOKYO OHKA KOGYO CO., LTD.
    Inventors: Yoshiyuki Utsumi, Takahiro Dazai, Jun Iwashita, Kenri Konno
  • Publication number: 20140128536
    Abstract: The present invention relates to an innovative (meth)acrylic reactive resin which cures with low odour or odourlessly. The present invention relates more particularly to reactive resins comprising high-boiling, reactive (meth)acrylic monomers from the group of the polar, cyclically substituted esters of (meth)acrylic acid, more particularly glycerol acetal, ketal or carbonate methacrylates. These new components are used as substitutes for MMA, which represents the major part of the odour nuisance in the existing, prior-art reactive resin systems. Using these new components it is possible to obtain resin formulations which have glass transition temperatures similar to, and properties comparable with, MMA-based resins. The innovative reactive resins are able in addition to exhibit more rapid curing than prior-art MMA-based systems. Reactive resins for the purposes of the invention are reactive monomer mixtures or mixtures of monomers and polymers that when used as a 2-component system can be readily cured.
    Type: Application
    Filed: July 2, 2012
    Publication date: May 8, 2014
    Applicant: Evonik Roehm GmbH
    Inventors: Stefan Hilf, Alexander Klein, Heike Heeb, Ingrid Kizewski, Sebastian Grimm, Michael Flittner
  • Publication number: 20140121326
    Abstract: A method for forming a conjugated heteroaromatic polymer is described, wherein at least one compound of formula (1) is polymerized using an acid as a catalyst, wherein X is selected from S, O, Se, Te, PR2 and NR2, Y is hydrogen (H) or a precursor of a good leaving group Y? whose conjugate acid (HY) has a pKa of less than 30, Z is hydrogen (H), silyl, or a good leaving group whose conjugate acid (HY) has a pKa of less than 30, b is 0, 1 or 2, each R1 is a substituent, and the at least one compound of formula (1) being polymerized includes at least one compound of formula (1) with Z?H and Y?H.
    Type: Application
    Filed: October 28, 2012
    Publication date: May 1, 2014
    Inventors: Chien-Chung Han, Balasubramanian Arumugam
  • Patent number: 8703890
    Abstract: This invention provides a polyfunctional polymer having high stereoregularity, in particular, isotacticity, and provides a production process thereof. The present invention relates to a polymer having, in a molecule, a repeating unit represented by General Formula (2): wherein R1 and R2 are different, and each represents a hydrogen atom, an alkyl group and an aryl group; * represents an asymmetrical carbon, the polymer containing meso diad (m) and racemo diad (r) at a proportion of 60:40 to 100:0 (m:r). The invention also relates to chemical modifications and a production process of the polymer.
    Type: Grant
    Filed: January 25, 2010
    Date of Patent: April 22, 2014
    Assignee: The University of Tokushima
    Inventor: Hitoshi Tanaka
  • Publication number: 20140093827
    Abstract: A resist pattern formation method including formation of a resist film, exposure, development, and subsequent rinsing using a resist composition containing a high-molecular compound having a constituent unit represented by the formula (a0-1), a constituent unit containing an acid decomposable group whose polarity increases by the action of an acid, and a constituent unit containing a group represented by the formula (a2-r-1). R represents a hydrogen atom, an alkyl group, or a halogenated alkyl group; Ra01 represents a lactone-containing polycyclic group, an —SO2-containing polycyclic group, or a cyano group-containing polycyclic group; Ra?21 represents a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, a halogenated alkyl group, a hydroxyl group, —COOR?, —OC(?O)R?, a hydroxyalkyl group, or a cyano group; R? represents a hydrogen atom or an alkyl group; and n? represents an integer of from 0 to 2.
    Type: Application
    Filed: September 20, 2013
    Publication date: April 3, 2014
    Applicant: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Yoichi Hori, Shinichi Hidesaka, Takeaki Shiroki
  • Publication number: 20140066581
    Abstract: The present invention relates to a process for radically curing a composition comprising a methacrylate containing compound (a1) and a monomer copolymerizable with said methacrylate containing compound in the presence of a 5 transition metal compound (c) and a peroxide, wherein the composition comprises a compound (b) according to formula (1) as monomer copolymerizable with said methacrylate containing compound whereby n=0-3; R1 and R2 each individually represent H, C1-C20 alkyl, C3-C20 cycloalkyl, C6-C20 aryl, C7-C20 alkylaryl or C7-C20 arylalkyl; X=O, S or NR3 whereby R3=H, C1C20 alkyl, C3-C20 cycloalkyl, C6-C20 aryl, C7-C20 alkylaryl, C7-C20 arylalkyl, part of a polymer chain or attached to a polymer chain, and the composition comprises at least one transition metal compound (c) selected from the group consisting of Co, Cu, Mn and Fe compounds, and the curing is effected in the presence of a peroxide selected from the group consisting of hydroperoxides, perketals, peresters, percarbonates and mixtures ther
    Type: Application
    Filed: March 29, 2012
    Publication date: March 6, 2014
    Applicant: DSM IP ASSETS B.V.
    Inventors: Iris Hilker, Johan Franz Gradus Antonius Jansen, Nanning Joerg Arfsten
  • Patent number: 8653190
    Abstract: Disclosed is a curable silicone composition for preparing release layers and pressure sensitive adhesives, and to substrates bearing a layer of the cured composition. More specifically, this invention relates to a silicone composition, curable in the absence of both catalysts and actinic radiation comprising a cyclic anhydride copolymer and an amine-terminated polysiloxane.
    Type: Grant
    Filed: August 8, 2011
    Date of Patent: February 18, 2014
    Assignee: 3M Innovative Properties Company
    Inventors: Joon Chatterjee, Timothy D. Filiatrault, Hae-Seung Lee, David S. Hays, Naimul Karim, Babu N. Gaddam
  • Publication number: 20140045122
    Abstract: A positive resist composition comprises a polymer having a carboxyl group substituted with an acid labile group having formula (1) wherein R1 and R2 are alkyl or alkenyl, R3 and R4 are a single bond, methylene, ethylene or propylene, R5 and R6 are hydrogen or alkyl. The composition has a high dissolution contrast, high resolution, and suppressed acid diffusion rate, and forms a pattern of good profile and minimal edge roughness.
    Type: Application
    Filed: August 1, 2013
    Publication date: February 13, 2014
    Applicant: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Jun Hatakeyama, Koji Hasegawa
  • Patent number: 8647808
    Abstract: A fluorinated monomer has formula (1) wherein R1 is H, F, methyl or trifluoromethyl, R2 and R3 are H or a monovalent hydrocarbon group, R4 to R6 each are a monovalent fluorinated hydrocarbon group, A is a divalent hydrocarbon group, and k1 is 0, 1 or 2. A polymer derived from the fluorinated monomer may be endowed with appropriate water repellency, water slip, acid lability and hydrolysis and is useful as an additive polymer in formulating a resist composition.
    Type: Grant
    Filed: April 6, 2011
    Date of Patent: February 11, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Masayoshi Sagehashi, Koji Hasegawa, Takeshi Sasami