Patents by Inventor Yuji Harada

Yuji Harada 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: 8431323
    Abstract: A fluorinated monomer of cyclic acetal structure has formula (1) wherein R is a C1-C20 alkyl group which may be substituted with halogen or separated by oxygen or carbonyl, and Z is a divalent organic group which forms a ring with alkylenoxy and contains a polymerizable unsaturated group. A polymer derived from the fluorinated monomer may be endowed with appropriate water repellency, water sliding property, lipophilicity, acid lability and hydrolyzability and is useful in formulating a protective coating composition and a resist composition.
    Type: Grant
    Filed: October 29, 2009
    Date of Patent: April 30, 2013
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takeru Watanabe, Satoshi Shinachi, Takeshi Kinsho, Koji Hasegawa, Yuji Harada, Jun Hatakeyama, Kazunori Maeda, Tomohiro Kobayashi
  • Patent number: 8420292
    Abstract: A polymer comprising recurring units of formula (1) and having a solubility in alkaline developer which increases under the action of an alkaline developer is provided. The polymer has transparency to radiation of up to 200 nm and improved water repellency, water slip, acid lability and hydrolysis and is useful as an additive polymer to formulate a resist composition. R1 is H, F, methyl, or trifluoromethyl, R2 is a monovalent fluorinated hydrocarbon group, An is a (n+1)-valent hydrocarbon or fluorinated hydrocarbon group, and n is 1, 2 or 3.
    Type: Grant
    Filed: January 14, 2011
    Date of Patent: April 16, 2013
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Yuji Harada, Takeru Watanabe, Takeshi Sasami, Yuuki Suka, Koji Hasegawa
  • Publication number: 20130084517
    Abstract: A protective film-forming composition comprising a polymer comprising fluorinated alcohol units of the structure: —C(CF3)2OR1 wherein R1 is H or a monovalent hydrocarbon group and having a Mw of 1,000-500,000 is applied onto a resist film to form a protective film thereon. The protective film-forming composition has high water repellent and water slip performance. The protective film exhibits barrier properties to water and prevents any resist components from being leached out in water.
    Type: Application
    Filed: August 30, 2012
    Publication date: April 4, 2013
    Applicant: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Yuuki Suka, Koji Hasegawa, Yuji Harada
  • Publication number: 20130065183
    Abstract: A resist composition is provided comprising a polymer comprising recurring units having a protected hydroxyl group, a photoacid generator, an organic solvent, and a hydroxyl-free polymeric additive comprising fluorinated recurring units. A negative pattern is formed by coating the resist composition, prebaking to form a resist film, exposing, baking, and developing the exposed film in an organic solvent-based developer to selectively dissolve the unexposed region of resist film.
    Type: Application
    Filed: September 7, 2012
    Publication date: March 14, 2013
    Applicant: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Tomohiro Kobayashi, Jun Hatakeyama, Masashi Iio, Yuuki Suka, Koji Hasegawa, Yuji Harada
  • Patent number: 8361703
    Abstract: A protective coating composition comprising a polymer of acyl-protected hexafluoroalcohol structure as a base polymer, optionally in admixture with a second polymer containing sulfonic acid amine salt in recurring units is applied onto a resist film. The protective coating is transparent to radiation of wavelength up to 200 nm.
    Type: Grant
    Filed: December 1, 2009
    Date of Patent: January 29, 2013
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Yuji Harada, Jun Hatakeyama, Koji Hasegawa
  • Patent number: 8323872
    Abstract: A resist protective coating material is provided comprising a polymer having a partial structure of formula (1) wherein R0 is H, F, alkyl or alkylene, and R1 is fluorinated alkyl or alkylene. In a pattern-forming process, the material forms on a resist film a protective coating which is water-insoluble, dissolvable in alkaline developer and immiscible with the resist film, allowing for effective implementation of immersion lithography. During alkali development, development of the resist film and removal of the protective coating can be simultaneously achieved.
    Type: Grant
    Filed: June 13, 2006
    Date of Patent: December 4, 2012
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Takeru Watanabe, Yuji Harada
  • Patent number: 8313886
    Abstract: An additive polymer comprising recurring units of formula (1) is added to a resist composition comprising a base resin, a photoacid generator, and an organic solvent. R1 is hydrogen or methyl, R2 is alkylene or fluoroalkylene, and R3 is fluoroalkyl. The additive polymer is highly transparent to radiation with wavelength of up to 200 nm. Water repellency, water slip, acid lability, hydrolysis and other properties of the polymer may be adjusted by a choice of polymer structure.
    Type: Grant
    Filed: April 15, 2010
    Date of Patent: November 20, 2012
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Yuji Harada, Jun Hatakeyama, Koji Hasegawa, Tomohiro Kobatashi
  • Publication number: 20120249995
    Abstract: The invention is a protective film material for immersion lithography that enables desirable immersion lithography, can be removed simultaneously with development of a photoresist layer, and has excellent process adaptability. The invention also includes a method for forming a pattern using the material. More specifically, the invention is a protective film material comprising (i) a blend of a polymer comprising a repeating unit having a fluorine-containing alkyl or alkylene group which contains at least one fluorine atom and an optional alkali soluble repeating unit and a polymer comprising a repeating unit having a fluorine-free alkyl group and an optional alkali soluble repeating unit, or (ii) a polymer comprising a repeating unit having a fluorine-containing alkyl or alkylene group which contains at least one fluorine atom and a repeating unit having a fluorine-free alkyl group and an optional alkali-soluble repeating unit.
    Type: Application
    Filed: June 12, 2012
    Publication date: October 4, 2012
    Applicant: SHIN-ETSU CHEMICAL CO. LTD.
    Inventors: Jun Hatakeyama, Yuji Harada, Takeru Watanabe
  • Patent number: 8268528
    Abstract: A resist composition is provided comprising (A) an additive polymer of acyl-protected hexafluoroalcohol structure, (B) a base polymer having a structure derived from lactone ring, hydroxyl group and/or maleic anhydride, the base polymer becoming soluble in alkaline developer under the action of acid, (C) a photoacid generator, and (D) an organic solvent. The additive polymer is transparent to radiation of wavelength up to 200 nm, and its properties can be tailored by a choice of the polymer structure.
    Type: Grant
    Filed: December 1, 2009
    Date of Patent: September 18, 2012
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Yuji Harada, Jun Hatakeyama, Koji Hasegawa, Kazunori Maeda, Tomohiro Kobayashi
  • Patent number: 8252504
    Abstract: A polymer obtained through copolymerization of a monomer having a hexafluoroalcohol pendant whose hydroxyl moiety has been protected and a monomer having an acid labile group is useful as an additive to a photoresist composition for immersion lithography. When processed by immersion lithography, the resist composition exhibits good water repellency and water slip and produces few development defects.
    Type: Grant
    Filed: February 13, 2009
    Date of Patent: August 28, 2012
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Yuji Harada, Jun Hatakeyama, Kazunori Maeda, Tomohiro Kobayashi
  • Publication number: 20120214100
    Abstract: There is disclosed a resist composition, wherein the composition is used in a lithography and comprises at least: a polymer (A) that becomes a base resin whose alkaline-solubility changes by an acid, a photo acid generator (B) generating a sulfonic acid represented by the following general formula (1) by responding to a high energy beam, and a polymer additive (C) represented by the following general formula (2). There can be provided a resist composition showing not only excellent lithography properties but also a high receding contact angle, and in addition, being capable of suppressing a blob defect in both the immersion exposures using and not using a top coat; and a patterning process using the same.
    Type: Application
    Filed: February 14, 2012
    Publication date: August 23, 2012
    Applicant: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Tomohiro Kobayashi, Youichi Ohsawa, Yuji Harada, Yuki Suka
  • Publication number: 20120148945
    Abstract: A polymer having a partial structure —C(CF3)2OH in recurring units is used as an additive to formulate a resist composition. A photoresist film formed from the resist composition has sufficient barrier performance against water to prevent any resist components from being leached in water and thus minimize any change of pattern profile.
    Type: Application
    Filed: December 13, 2011
    Publication date: June 14, 2012
    Applicant: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Koji Hasegawa, Takeshi Sasami, Yuji Harada, Taku Morisawa
  • Patent number: 8158330
    Abstract: A protective coating composition comprising a copolymer of an alkali-soluble (?-trifluoromethyl) acrylate and a norbornene derivative as a base polymer, optionally in admixture with a second polymer containing sulfonic acid and/or sulfonic acid amine salt in repeat units is applied onto a resist film. The protective coating is effective in minimizing development defects and forming a resist pattern of improved profile.
    Type: Grant
    Filed: May 11, 2009
    Date of Patent: April 17, 2012
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Yuji Harada, Jun Hatakeyama, Koji Hasegawa, Satoshi Shinachi
  • Publication number: 20120083580
    Abstract: A fluorinated ester monomer is provided having formula (1) wherein R1 is H, CH3 or CF3, R2 and R3 are H or a monovalent hydrocarbon group, or R2 and R3 forms a hydrocarbon ring, R4 is a monovalent hydrocarbon group, and k is 0 or 1. A polymer obtained from the monomer has transparency to radiation with a wavelength of up to 200 nm and appropriate alkaline hydrolysis, is constructed such that any of water repellency, water slip and surface segregation may be adjusted by a choice of its structure, and is useful in forming ArF immersion lithography materials.
    Type: Application
    Filed: September 22, 2011
    Publication date: April 5, 2012
    Inventors: Takeshi KINSHO, Yuuki Suka, Yuji Harada, Koji Hasegawa, Takeshi Sasami
  • Patent number: 8101335
    Abstract: A copolymer of an alkali-soluble (?-trifluoromethyl)-acrylate and a norbornene derivative is useful as an additive to a resist composition. When processed by immersion lithography, the resist composition exhibits excellent water repellency and water slip and forms a pattern with few development defects.
    Type: Grant
    Filed: May 11, 2009
    Date of Patent: January 24, 2012
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Yuji Harada, Jun Hatakeyama, Kazunori Maeda, Koji Hasegawa, Satoshi Shinachi
  • Patent number: 8088537
    Abstract: The present invention relates to a resist top coat composition and a patterning process adopting such a material, which resist top coat composition is provided for forming a top coat on a photoresist film so as to protect the photoresist film, in liguid immersion photolithography.
    Type: Grant
    Filed: January 21, 2009
    Date of Patent: January 3, 2012
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Yuji Harada
  • Publication number: 20110305979
    Abstract: The invention provides a resist top coat composition wherein the composition contains polymer (P1-1) with a weight-average molecular weight of 1,000 to 500,000, having at least repeating units represented by the following general formulae (1a), (1b-1), and (1c). There can be a resist top coat composition having excellent water repellent and water sliding properties with fewer development defects and with a good resist pattern profile after development, and a patterning process using this composition.
    Type: Application
    Filed: May 26, 2011
    Publication date: December 15, 2011
    Applicant: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Yuji HARADA, Taku MORISAWA, Takeru WATANABE, Yuki SUKA
  • Patent number: 8057981
    Abstract: A polymer obtained through copolymerization of a monomer having a hexafluoroalcohol pendant and a monomer having a hexafluoroalcohol pendant whose hydroxyl moiety has been protected is useful as an additive to a photoresist composition and as a protective coating material for immersion lithography. When processed by immersion lithography, the resist composition and protective coating composition exhibit good water repellency and water slip and produce few development defects.
    Type: Grant
    Filed: February 13, 2009
    Date of Patent: November 15, 2011
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Yuji Harada, Jun Hatakeyama, Kazunori Maeda, Tomohiro Kobayashi
  • Patent number: 8043788
    Abstract: To a resist composition comprising a polymer which changes its alkali solubility under the action of an acid as a base resin, is added a copolymer comprising recurring units containing amino and recurring units containing ?-trifluoromethylhydroxy as an additive. The composition is suited for immersion lithography.
    Type: Grant
    Filed: July 2, 2008
    Date of Patent: October 25, 2011
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Tomohiro Kobayashi, Jun Hatakeyama, Yuji Harada
  • Publication number: 20110177455
    Abstract: A polymer comprising recurring units of formula (1) and having a solubility in alkaline developer which increases under the action of an alkaline developer is provided. The polymer has transparency to radiation of up to 200 nm and improved water repellency, water slip, acid lability and hydrolysis and is useful as an additive polymer to formulate a resist composition. R1 is H, F, methyl, or trifluoromethyl, R2 is a monovalent fluorinated hydrocarbon group, An is a (n+1)-valent hydrocarbon or fluorinated hydrocarbon group, and n is 1, 2 or 3.
    Type: Application
    Filed: January 14, 2011
    Publication date: July 21, 2011
    Inventors: Yuji HARADA, Takeru Watanabe, Takeshi Sasami, Yuuki Suka, Koji Hasegawa