Patents by Inventor Masaki Ohashi

Masaki Ohashi has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).

  • Patent number: 8957160
    Abstract: A sulfonic acid anion-containing polymer having a triarylsulfonium cation is prepared by (1) preparing a sulfonic acid anion-containing polymer having an ammonium or metal cation not bound thereto, (2) purifying the polymer by water washing or crystallization, and (3) then reacting the polymer with a triarylsulfonium salt. A resist composition comprising the inventive polymer is effective for controlling acid diffusion since the sulfonium salt is bound to the polymer backbone.
    Type: Grant
    Filed: February 15, 2013
    Date of Patent: February 17, 2015
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Masaki Ohashi, Tomohiro Kobayashi, Masayoshi Sagehashi
  • Patent number: 8956803
    Abstract: The present invention provides a sulfonium salt used in a resist composition that can give a pattern having a high resolution, especially an excellent rectangularity of a pattern form and a small roughness, while not readily generating a defect, in the photolithography using a high energy beam as a light source; a resist composition that contains the sulfonium salt; and a patterning process using this resist composition, wherein the sulfonium salt is shown by the following general formula (1a), wherein each of R and R0 independently represents a hydrogen atom, or a linear, branched, or cyclic monovalent hydrocarbon group having 1 to 30 carbon atoms which may be optionally substituted by a heteroatom or interposed by a heteroatom.
    Type: Grant
    Filed: December 6, 2013
    Date of Patent: February 17, 2015
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Masaki Ohashi, Tomohiro Kobayashi, Akihiro Seki, Masayoshi Sagehashi, Masahiro Fukushima
  • Publication number: 20140377706
    Abstract: An aqueous solution containing 0.1-20 wt % of a substituted choline or thiocholine hydroxide is a useful developer for photosensitive resist materials. A resist pattern is formed by applying a chemically amplified positive resist composition onto a substrate to form a resist film, exposing the resist film to high-energy radiation, and developing the exposed resist film in an ammonium hydroxide-containing aqueous solution.
    Type: Application
    Filed: May 27, 2014
    Publication date: December 25, 2014
    Applicant: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Jun Hatakeyama, Masaki Ohashi
  • Publication number: 20140370441
    Abstract: An aqueous solution containing 0.1-20 wt % of a cyclic ammonium hydroxide is a useful developer for photosensitive resist materials. A resist pattern is formed by applying a chemically amplified positive resist composition onto a substrate to form a resist film, exposing the resist film to high-energy radiation, and developing the exposed resist film in a cyclic ammonium hydroxide-containing aqueous solution.
    Type: Application
    Filed: May 27, 2014
    Publication date: December 18, 2014
    Applicant: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Jun Hatakeyama, Masaki Ohashi
  • Patent number: 8900796
    Abstract: The present invention provides an acid generator generates a sulfonic acid represented by the following general formula (1) in response to high-energy beam or heat: To provide a novel acid generator which is suitably used as an acid generator for a resist composition, which solves the problems of LER and a depth of focus and can be effectively and widely used particularly without degradation of a resolution, a chemically amplified resist composition using the same, and a patterning process.
    Type: Grant
    Filed: February 15, 2013
    Date of Patent: December 2, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Masaki Ohashi, Tomohiro Kobayashi, Masayoshi Sagehashi
  • Publication number: 20140322650
    Abstract: A negative pattern is formed by coating a resist composition comprising a polymer comprising recurring units of formulae (1) and (2) and a photoacid generator of formula (3) onto a substrate, baking, exposure, PEB and developing in an organic solvent. In formulae (1) and (2), R1 is H, F, CH3 or CF3, Z is a single bond, phenylene, naphthylene, or (backbone)-C(?O)—O—Z?—, Z? is alkylene, phenylene or naphthylene, XA is an acid labile group, YL is H or a polar group. In formula (3), R2 and R3 are a monovalent hydrocarbon group, R4 is a divalent hydrocarbon group, or R2 and R3, or R2 and R4 may form a ring with the sulfur, L is a single bond or a divalent hydrocarbon group, Xa and Xb are H, F or CF3, and k is an integer of 1 to 4.
    Type: Application
    Filed: April 10, 2014
    Publication date: October 30, 2014
    Applicant: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Masaki Ohashi, Masahiro Fukushima, Tomohiro Kobayashi, Kazuhiro Katayama, Chuanwen Lin
  • Publication number: 20140296561
    Abstract: A sulfonium salt having a 4-fluorophenyl group is introduced as recurring units into a polymer comprising hydroxyphenyl(meth)acrylate units and acid labile group-containing (meth)acrylate units to form a polymer which is useful as a base resin in a resist composition. The resist composition has a high sensitivity, high resolution and minimized LER.
    Type: Application
    Filed: June 17, 2014
    Publication date: October 2, 2014
    Inventors: Youichi OHSAWA, Masaki OHASHI, Seiichiro TACHIBANA, Jun HATAKEYAMA
  • Patent number: 8841482
    Abstract: A rare earth metal extractant containing, as the extractant component, dialkyldiglycol amide acid which is excellent in breaking down light rare earth elements is reacted in diglycolic acid (X mol) and an esterification agent (Y mol) at a reaction temperature of 70° C. or more and for a reaction time of one hour or more such that the mol ratio of Y/X is 2.5 or more, and is subjected to vacuum concentration. Subsequently, a reaction intermediate product is obtained by removing unreacted products and reaction residue, and an aprotic polar solvent is added as the reaction solvent. Then, the reaction intermediate product is reacted with dialkyl amine (Z mol) such that the mol ratio of Z/X is 0.9 or more and the aprotic polar solvent is removed. As a consequence, a rare earth metal extractant is efficiently synthesized at a low cost and at a high yield without having to use expensive diglycolic acid anhydride and harmful dichloromethane.
    Type: Grant
    Filed: July 1, 2011
    Date of Patent: September 23, 2014
    Assignees: Shin-Etsu Chemical Co., Ltd., Japan Atomic Energy Agency
    Inventors: Kazuaki Sakaki, Hiroto Sugahara, Tetsuya Kume, Masaki Ohashi, Hirochika Naganawa, Kojiro Shimojo
  • Publication number: 20140272707
    Abstract: A sulfonium salt having formula (1a) is provided wherein R1 is H, F, CH3 or CF3, R1a to R1m are each independently H or a monovalent hydrocarbon group, L is a single bond or divalent hydrocarbon group, X is a divalent alkylene group optionally substituted with fluorine, and n is 0 or 1. The sulfonium salt having a polymerizable anion provides for efficient scission of acid labile groups in a chemically amplified resist composition, and it is a very useful monomer from which a base resin for resist use is prepared.
    Type: Application
    Filed: February 4, 2014
    Publication date: September 18, 2014
    Applicant: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Masahiro Fukushima, Jun Hatakeyama, Masaki Ohashi, Teppei Adachi
  • Publication number: 20140255843
    Abstract: A negative pattern is formed by coating a resist composition comprising (A) a polymer having an acid labile group, adapted to change its polarity under the action of acid, (B) a photoacid generator, and (C) an organic solvent onto a substrate, baking, exposing the resist film to high-energy radiation, PEB, and developing in an organic solvent-based developer to selectively dissolve the unexposed region of resist film. The photoacid generator has the formula: R1—COOC(CF3)2—CH2SO3?R2R3R4S+ wherein R1 is a monovalent hydrocarbon group, R2, R3 and R4 are an alkyl, alkenyl, oxoalkyl, aryl, aralkyl or aryloxoalkyl group, or may bond together to form a ring with the sulfur atom.
    Type: Application
    Filed: February 18, 2014
    Publication date: September 11, 2014
    Applicant: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Tomohiro Kobayashi, Kazuhiro Katayama, Kentaro Kumaki, Chuanwen Lin, Masaki Ohashi, Masahiro Fukushima
  • Patent number: 8815492
    Abstract: A chemically amplified positive resist composition comprising (A) a triarylsulfonium salt of 2,3,3,3-tetrafluoro-2-(1,1,2,2,3,3,3-heptafluoropropoxy)propionic acid, (B) an acid generator, (C) a base resin, and (D) an organic solvent is suited for ArF immersion lithography. The sulfonium salt is highly hydrophobic and little leached out in immersion water. By virtue of controlled acid diffusion, a pattern profile with high resolution can be constructed.
    Type: Grant
    Filed: September 14, 2012
    Date of Patent: August 26, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Masaki Ohashi, Takeshi Sasami, Jun Hatakeyama
  • Patent number: 8785105
    Abstract: A sulfonium salt having a 4-fluorophenyl group is introduced as recurring units into a polymer comprising hydroxyphenyl (meth)acrylate units and acid labile group-containing (meth)acrylate units to form a polymer which is useful as a base resin in a resist composition. The resist composition has a high sensitivity, high resolution and minimized LER.
    Type: Grant
    Filed: November 9, 2011
    Date of Patent: July 22, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Masaki Ohashi, Seiichiro Tachibana, Jun Hatakeyama
  • Publication number: 20140199630
    Abstract: A sulfonium salt used in a resist composition which gives a pattern having a high resolution, and small roughness in the photolithography using a high energy beam as a light source, and further difficultly eluted in water in the immersion lithography, and a resist composition containing the sulfonium salt, and a patterning process using the resist composition, wherein the sulfonium salt is represented by the following general formula (1a), wherein R represents a linear, branched, or cyclic monovalent hydrocarbon group having 1 to 30 carbon atoms at least one or more of the hydrogen atoms of which are substituted by a fluorine atom, R0 represents a hydrogen atom, or a linear, branched, or cyclic monovalent hydrocarbon group having 1 to 30 carbon atoms which may be substituted by a halogen atom, or interposed by a heteroatom.
    Type: Application
    Filed: December 11, 2013
    Publication date: July 17, 2014
    Applicant: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Masaki OHASHI, Tomohiro KOBAYASHI, Akihiro SEKI, Masayoshi SAGEHASHI, Masahiro FUKUSHIMA
  • Publication number: 20140199629
    Abstract: The present invention provides a sulfonium salt used in a resist composition that can give a pattern having a high resolution, especially an excellent rectangularity of a pattern form and a small roughness, while not readily generating a defect, in the photolithography using a high energy beam as a light source; a resist composition that contains the sulfonium salt; and a patterning process using this resist composition, wherein the sulfonium salt is shown by the following general formula (1a), wherein each of R and R0 independently represents a hydrogen atom, or a linear, branched, or cyclic monovalent hydrocarbon group having 1 to 30 carbon atoms which may be optionally substituted by a heteroatom or interposed by a heteroatom.
    Type: Application
    Filed: December 6, 2013
    Publication date: July 17, 2014
    Applicant: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Masaki OHASHI, Tomohiro KOBAYASHI, Akihiro SEKI, Masayoshi SAGEHASHI, Masahiro FUKUSHIMA
  • Publication number: 20140162188
    Abstract: A positive resist composition is provided comprising a polymer comprising recurring styrene units having an ester group bonded to a CF3—C(OH)—R3 group (R3?H, CH3, or CF3) such as 1,1,1,3,3,3-hexafluoro-2-propanol 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: November 15, 2013
    Publication date: June 12, 2014
    Applicant: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Jun Hatakeyama, Koji Hasegawa, Masaki Ohashi
  • Publication number: 20140162189
    Abstract: A sulfonium salt having formula (1a) is provided wherein R1 is H, F, CH3 or CF3, R1a to R1m are each independently H or a monovalent hydrocarbon group, L is a single bond or divalent hydrocarbon group, X is a divalent alkylene group optionally substituted with fluorine, and n is 0 or 1. The sulfonium salt having a polymerizable anion provides for efficient scission of acid labile groups in a chemically amplified resist composition, and it is a very useful monomer from which a base resin for resist use is prepared.
    Type: Application
    Filed: December 6, 2013
    Publication date: June 12, 2014
    Applicant: Shin-Etsu Chemical Co., Ltd.
    Inventors: Masaki Ohashi, Jun Hatakeyama, Teppei Adachi, Masahiro Fukushima
  • Patent number: 8748076
    Abstract: There is disclosed a resist composition comprising at least: (A) a polymer containing one or more repeating units having a structure shown by the following general formula (1) and/or (2), an alkaline-solubility of the polymer being increased by an acid, (B) a photo acid generator generating, with responding to a high energy beam, a sulfonic acid shown by the following general formula (3), and (C) an onium sulfonate shown by the following general formula (4). There can be a resist composition showing not only excellent LWR and pattern profile but also extremely good performance in pattern-fall resistance, and to provide a patterning process using the same.
    Type: Grant
    Filed: January 6, 2012
    Date of Patent: June 10, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takayuki Nagasawa, Tomohiro Kobayashi, Ryosuke Taniguchi, Masaki Ohashi
  • Patent number: 8741554
    Abstract: A pattern is formed by coating a first positive resist composition comprising a base resin, a photoacid generator, and a base generator onto a substrate to form a first resist film, patternwise exposure, PEB, and development to form a first resist pattern, heating the first resist pattern for causing the base generator to generate a base for inactivating the pattern to acid, coating a second positive resist composition comprising a C3-C8 alcohol and an optional C6-C12 ether onto the first resist pattern-bearing substrate to form a second resist film, patternwise exposure, PEB, and development to form a second resist pattern.
    Type: Grant
    Filed: May 26, 2010
    Date of Patent: June 3, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Kazuhiro Katayama, Youichi Ohsawa, Masaki Ohashi
  • Patent number: 8741546
    Abstract: A pattern is formed by coating a first positive resist composition comprising a copolymer comprising lactone-containing recurring units, acid labile group-containing recurring units and carbamate-containing recurring units, and a photoacid generator onto a substrate to form a first resist film, patternwise exposure, PEB, and development to form a first resist pattern, heating the first resist pattern for inactivation to acid, coating a second positive resist composition comprising a C3-C8 alcohol and an optional C6-C12 ether onto the first resist pattern-bearing substrate to form a second resist film, patternwise exposure, PEB, and development to form a second resist pattern.
    Type: Grant
    Filed: March 15, 2013
    Date of Patent: June 3, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Kazuhiro Katayama, Youichi Ohsawa, Masaki Ohashi
  • Patent number: 8722307
    Abstract: A composition comprising a polymer comprising repeat units selected from formulae (1) to (4), an aromatic ring-containing polymer, a near-infrared absorbing dye, and a solvent is used to form a near-infrared absorptive film. R1, R7, R9, and R14 are H, methyl, fluorine or trifluoromethyl, R2 to R6 are H, F, trifluoromethyl, —C(CF3)2OR16, alkyl or alkoxy, at least one of R2 to R6 being F or a fluorinated group, R16, R8 and R13 are H or a monovalent organic group, L1 is a single bond or —C(?O)O—, m is 0 or 1, L2 is a di- or trivalent hydrocarbon group, n is 1 or 2, R10 to R12 are H, hydroxyl, halogen or a monovalent organic group, and R15 is a fluorinated C2-C15 hydrocarbon group.
    Type: Grant
    Filed: May 27, 2011
    Date of Patent: May 13, 2014
    Assignees: International Business Machines Corporation, Shin-Etsu Chemical Co., Ltd.
    Inventors: Seiichiro Tachibana, Kazumi Noda, Masaki Ohashi, Takeshi Kinsho, Wu-Song Huang, Dario L. Goldfarb, Wai-Kin Li, Martin Glodde