Patents Examined by John Chu
  • Patent number: 9261782
    Abstract: Various cycloolefinic/maleic anhydride polymers containing maleimide pendant groups and compositions thereof useful for forming self-imageable films encompassing such copolymers are disclosed. Such polymers encompass norbornene-type repeating units containing maleimide groups and maleic anhydride-type repeating units where at least some of such maleic anhydride-type repeating units have been ring-opened. The films formed from such copolymer compositions provide self imageable, low-k, thermally stable layers for use in microelectronic and optoelectronic devices.
    Type: Grant
    Filed: September 24, 2013
    Date of Patent: February 16, 2016
    Assignee: PROMERUS, LLC
    Inventors: Pramod Kandanarachchi, Larry F. Rhodes
  • Patent number: 9255079
    Abstract: New methods are provided for synthesis of photoacid generator compounds (“PAGs”), new photoacid generator compounds and photoresist compositions that comprise such PAG compounds. In a particular aspect, sulfonium-containing (S+) photoacid generators and methods of synthesis of sulfonium photoacid generators are provided.
    Type: Grant
    Filed: December 10, 2010
    Date of Patent: February 9, 2016
    Assignee: Rohm and Haas Electronic Materials, LLC
    Inventors: Mingqi Li, Emad Aqad, Cong Liu, Joseph Mattia, Cheng-Bai Xu, George G. Barclay
  • Patent number: 9244355
    Abstract: New photoresist compositions are provided that are useful for immersion lithography. Preferred photoresist compositions of the invention comprise one or more materials having a water contact angle that can be changed by treatment with base and/or one or more materials that comprise fluorinated photoacid-labile groups and/or one or more materials that comprise acidic groups spaced from a polymer backbone. Particularly preferred photoresists of the invention can exhibit reduced leaching of resist materials into an immersion fluid contacting the resist layer during immersion lithography processing.
    Type: Grant
    Filed: October 30, 2007
    Date of Patent: January 26, 2016
    Assignee: Rohm and Haas Electronic Materials, LLC
    Inventors: Stefan J. Caporale, George G. Barclay, Deyan Wang, Li Jia
  • Patent number: 9200098
    Abstract: A radiation-sensitive composition includes a photoacid generator shown by a general formula (0-1a). Each of R0 individually represents a substituted or unsubstituted organic group which includes a carbon atom, a hydrogen atom, and an oxygen atom, and which includes at least one ester bond, and M+ represents a monovalent onium cation. A compound is shown by a general formula (0). R represents a substituted or unsubstituted organic group which includes a carbon atom, a hydrogen atom, and an oxygen atom, and which includes at least one ester bond, and M+ represents a monovalent onium cation.
    Type: Grant
    Filed: March 8, 2012
    Date of Patent: December 1, 2015
    Assignee: JSR CORPORATION
    Inventor: Ken Maruyama
  • Patent number: 9164381
    Abstract: A resist composition including a base component (A) which exhibits changed solubility in a developing solution under action of acid and an acid generator component (B) which generates acid upon exposure, the acid generator component (B) including a sulfonium compound (B1) having a sulfonio group and an anion group represented by general formula (b1-r-1) shown below in one molecule thereof (wherein Y1 represents a divalent linking group or a single bond; L1 represents an ester bond or a single bond; V1 represents a divalent hydrocarbon group having a fluorine atom; and n represents 0 or 1, provided that, when L1 represents a single bond, n=1).
    Type: Grant
    Filed: May 29, 2013
    Date of Patent: October 20, 2015
    Assignee: TOKYO OHKA KOGYO CO., LTD.
    Inventors: Yoshitaka Komuro, Shinji Kumada
  • Patent number: 9158191
    Abstract: A chemically amplified negative resist composition is provided comprising (A) a resin having a crosslinking group, (B) a crosslinker, (C) a photoacid generator capable of generating an acid upon exposure to light of wavelength 190-500 nm, (D) a solvent, and (E) a fluoroalkyl-containing amine compound. The resist composition can form a fine pattern, specifically a fine hole or space pattern which has a positive taper (or forward taper) profile in which the size of top is greater than the size of bottom or improves the overhang profile with extremely projected top.
    Type: Grant
    Filed: December 5, 2012
    Date of Patent: October 13, 2015
    Assignee: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Katsuya Takemura, Takeru Watanabe, Takashi Miyazaki
  • Patent number: 9140981
    Abstract: Provided are an actinic-ray-sensitive or a radiation-sensitive resin composition with greater residual film ratio and capable of suppressing pattern collapse and an occurrence of bridge defects after development, and a resist film, a pattern forming method, an electronic device manufacturing method, and an electronic device, each using the same. An actinic-ray-sensitive or radiation-sensitive resin composition includes a resin (P) having a repeating unit (a) represented by following General Formula (I), a compound (B) represented by any of following General Formulae (B-1) to (B-3), and a solvent, in General Formula (I), R0 represents a hydrogen atom or a methyl group, and R1, R2 and R3 each independently represent a straight chain or branched alkyl group.
    Type: Grant
    Filed: September 13, 2012
    Date of Patent: September 22, 2015
    Assignee: FUJIFILM Corporation
    Inventors: Kaoru Iwato, Hidenori Takahashi, Michihiro Shirakawa
  • Patent number: 9134607
    Abstract: A photoresist composition comprising a resin which comprises a structural unit represented by formula (I); wherein R1 represents a hydrogen atom or a methyl group, and R2 represents C1-C10 hydrocarbon group; and a resin which comprises a structural unit having an acid-labile group and no structural unit represented by formula (I); and an acid generator represented by formula (II): wherein X2 represents a C1-C6 alkanediyl group where a hydrogen atom can be replaced by a hydroxyl group or a group —O—R5 and where a methylene group can be replaced by an oxygen atom or a carbonyl group, R4 and R5 each independently represent a C1-C24 hydrocarbon group where a hydrogen atom can be replaced by a fluorine atom or a hydroxyl group and where a methylene group can be replaced by an oxygen atom or a carbonyl group, and Z+ represents an organic cation.
    Type: Grant
    Filed: July 15, 2013
    Date of Patent: September 15, 2015
    Assignee: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Tatsuro Masuyama, Satoshi Yamaguchi
  • Patent number: 9134608
    Abstract: A positive photosensitive resin composition including: (a) a resin capable of being dissolved in an aqueous alkaline solution; (b) a compound having two or more oxetanyl groups; (c) a diazonaphthoquinone compound; and (d) a solvent.
    Type: Grant
    Filed: January 18, 2011
    Date of Patent: September 15, 2015
    Assignee: HITACHI CHEMICAL DUPONT MICROSYSTEMS, LTD.
    Inventors: Masashi Kotani, Masayuki Ooe, Taku Konno, Tomonori Minegishi, Keishi Ono
  • Patent number: 9115074
    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: December 27, 2013
    Date of Patent: August 25, 2015
    Assignee: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Masayoshi Sagehashi, Koji Hasegawa, Takeshi Sasami
  • Patent number: 9104101
    Abstract: A resist composition including a resin component which generates acid upon exposure and exhibits changed solubility in a developing solution under the action of acid, the resin component including a resin component having a structural unit represented by a general formula (a0-0-1) shown below in which R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms, R0-1 represents a single bond or a divalent linking group, each of R2, R3 and R4 independently represents a linear, branched or cyclic alkyl group which may have a non-aromatic substituent, or R3 and R4 may be bonded to each other to form a ring together with the sulfur atom, and X represents a non-aromatic divalent linking group or a single bond.
    Type: Grant
    Filed: February 22, 2012
    Date of Patent: August 11, 2015
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Kensuke Matsuzawa, Jun Iwashita, Yoshitaka Komuro, Masatoshi Arai
  • Patent number: 9097969
    Abstract: A compound represented by general formula (b1) shown below (in the formula, Y1 represents a divalent linking group; W represents S, Se or I; R1 represents a hydrocarbon group; represents an alkyl group of 1 to 5 carbon atoms or an alkoxy group of 1 to 5 carbon atoms; when W represents I, m+n=2, and when W represents S or Se, m+n=3, provided that m?1 and n?0; p represents an integer of 0 to 5; and X? represents a counteranion.
    Type: Grant
    Filed: June 11, 2013
    Date of Patent: August 4, 2015
    Assignee: TOKYO OHKA KOGYO CO., LTD.
    Inventors: Yoshiyuki Utsumi, Hideto Nito
  • Patent number: 9091917
    Abstract: Provided is a photoresist composition containing a polymer that contains, as a constituent unit, a specific methacrylic acid ester derivative. The photoresist composition can form a photoresist pattern with improved LWR and high resolution. More specifically, provided is an acrylic acid ester derivative represented by the following general formula (1): wherein R1 is a hydrogen atom or a methyl group; and A represents the following general formula (A-1) or (A-2): wherein R2 and R3 are each independently an alkyl group having 1 to 6 carbon atoms or a cyclic hydrocarbon group having 3 to 6 carbon atoms; Z is CH2 or —O—; and n is 0 or 1; with the proviso that in (A-1) there is no case where R2 is a methyl group and Z is CH2 and n is 1.
    Type: Grant
    Filed: January 18, 2012
    Date of Patent: July 28, 2015
    Assignee: KURARAY CO., LTD.
    Inventor: Osamu Nakayama
  • Patent number: 9091927
    Abstract: A positive resist composition contains: (A) a polymer compound having a structure where a hydrogen atom of a phenolic hydroxyl group is replaced by an acid labile group represented by the following formula (I): wherein R represents a monovalent organic group; A represents a group having a polycyclic hydrocarbon ring structure or a group having a polycyclic heterocyclic structure; and * represents a bonding position to an oxygen atom of the phenolic hydroxyl group.
    Type: Grant
    Filed: November 6, 2013
    Date of Patent: July 28, 2015
    Assignee: FUJIFILM Corporation
    Inventors: Tomotaka Tsuchimura, Takeshi Inasaki
  • Patent number: 9091933
    Abstract: A negative pattern is formed by applying a resist composition comprising (A) a polymer comprising recurring units (a1) having a carboxyl group protected with an acid labile group and recurring units (a2) having an amino group, amide bond, carbamate bond or nitrogen-containing heterocycle, (B) a photoacid generator, and (C) an organic solvent onto a substrate, prebaking, exposing, baking, and selectively dissolving an unexposed region of the resist film in an organic solvent-based developer.
    Type: Grant
    Filed: November 16, 2012
    Date of Patent: July 28, 2015
    Assignee: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Tomohiro Kobayashi, Kazuhiro Katayama, Jun Hatakeyama, Kenji Funatsu, Seiichiro Tachibana
  • Patent number: 9086624
    Abstract: A polymer comprising recurring units derived from a (meth)acrylate monomer of tertiary ester type having branched alkyl on alicycle is used to form a resist composition. When subjected to exposure, PEB and organic solvent development, the resist composition is improved in dissolution contrast.
    Type: Grant
    Filed: August 1, 2013
    Date of Patent: July 21, 2015
    Assignee: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Masayoshi Sagehashi, Jun Hatakeyama, Koji Hasegawa
  • Patent number: 9081290
    Abstract: A negative pattern is formed by coating a resist composition comprising a polymer comprising recurring units having a carboxyl group substituted with an acid labile group of tertiary ester and an optional acid generator onto a substrate, prebaking, exposing to high-energy radiation, baking, and developing in an organic solvent developer so that the unexposed region of resist film is dissolved away and the exposed region of resist film is not dissolved. The resist composition exhibits a high dissolution contrast during organic solvent development and forms a fine hole or trench pattern at a high sensitivity and dimensional control.
    Type: Grant
    Filed: June 17, 2013
    Date of Patent: July 14, 2015
    Assignee: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Jun Hatakeyama, Koji Hasegawa, Masayoshi Sagehashi, Kazuhiro Katayama, Kentaro Kumaki, Tomohiro Kobayashi
  • Patent number: 9051247
    Abstract: A salt represented by formula (I): wherein Q1 and Q2 independently each represent a fluorine atom or a C1-C6 perfluoroalkyl group, n represents 0 or 1, Ll represents a single bond or a C1-C10 alkanediyl group in which a methylene group may be replaced by an oxygen atom or carbonyl group, provided that Ll is not a single bond when n is 0, ring W represents a C3-C36 aliphatic ring in which a methylene group may be replaced by an oxygen atom, a sulfur atom, a carbonyl group or a sulfonyl group and in which a hydrogen atom may be replaced by a hydroxyl group, a C1-C12 alkyl group or a C1-C12 alkoxy group, Rl represents a hydroxyl group or a hydroxyl group protected by a protecting group, and Z+ represents an organic cation.
    Type: Grant
    Filed: April 10, 2012
    Date of Patent: June 9, 2015
    Assignee: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Yukako Anryu, Koji Ichikawa
  • Patent number: 9052594
    Abstract: A positive photosensitive composition includes: a resin (A) whose dissolution rate in an alkaline developing solution increases by the action of an acid, the resin (A) containing an acid decomposable repeating unit represented by a general formula (I) and an acid nondecomposable repeating unit represented by a general formula (II); and a compound (B) capable of generating an acid upon irradiation with one of active rays and radiations: wherein Xa1 represents one of a hydrogen atom, an alkyl group, a cyano group, and a halogen atom, A1 represents one of a single bond and a divalent connecting group, ALG represents an acid leaving hydrocarbon group, Xa2 represents one of a hydrogen atom, an alkyl group, a cyano group, and a halogen atom, A2 represents one of a single bond and a divalent connecting group, and ACG represents an acid nonleaving hydrocarbon group.
    Type: Grant
    Filed: November 10, 2011
    Date of Patent: June 9, 2015
    Assignee: FUJIFILM Corporation
    Inventors: Hyou Takahashi, Naoya Sugimoto, Kunihiko Kodama, Kei Yamamoto
  • Patent number: 9046766
    Abstract: An actinic ray-sensitive or radiation-sensitive resin composition comprises (A) a resin that exhibits an increased solubility in an alkali developer when acted on by an acid, and (B) at least two types of sulfonic acid generators that generate a sulfonic acid when exposed to actinic rays or radiation, wherein the two types of sulfonic acid generators (B) consist of sulfonic acid generators (B1) and (B2) satisfying the following requirements, namely the sulfonic acid generator (B1) generates a sulfonic acid composed of 9 to 20 elements with an acid strength (pKa) satisfying the relationship pKa<?3.50, and the sulfonic acid generator (B2) generates an acid composed of 17 or more elements with an acid strength (pKa) satisfying the relationship ?2.00>pKa??3.50, provided that no hydrogen atom is included in the number of elements of the generated acids.
    Type: Grant
    Filed: July 8, 2009
    Date of Patent: June 2, 2015
    Assignee: FUJIFILM Corporation
    Inventors: Takayuki Kato, Michihiro Shirakawa, Hyou Takahashi