Polymer Of Unsaturated Acid Or Ester Patents (Class 430/910)
  • Patent number: 7939241
    Abstract: The present invention relates to a novel (meth)acrylamide compound represented by the general formula (1), a (co)polymer of the (meth)acrylamide compound, and a chemically amplified photosensitive resin composition composed of the polymer and a photoacid generator. In the formula, R1 represents a hydrogen atom or a methyl group; R2 represents an acid-decomposable group; and R3 to R6 independently represent a hydrogen atom, a halogen atom or an alkyl group having 1 to 4 carbon atoms.
    Type: Grant
    Filed: May 12, 2006
    Date of Patent: May 10, 2011
    Assignee: NEC Corporation
    Inventors: Katsumi Maeda, Kaichirou Nakano
  • Patent number: 7927780
    Abstract: A compound represented by formula (I); and a compound represented by formula (b1-1): wherein X represents —O—, —S—, —O—R3— or —S—R4—, wherein each of R3 and R4 independently represents an alkylene group of 1 to 5 carbon atoms; R2 represents an alkyl group of 1 to 6 carbon atoms, an alkoxy group of 1 to 6 carbon atoms, a halogenated alkyl group of 1 to 6 carbon atoms, a halogen atom, a hydroxyalkyl group of 1 to 6 carbon atoms, a hydroxyl group or a cyano group; a represents an integer of 0 to 2; Q1 represents an alkylene group of 1 to 12 carbon atoms or a single bond; Y1 represents an alkylene group of 1 to 4 carbon atoms or a fluorinated alkylene group; M+ represents an alkali metal ion; and A+ represents an organic cation.
    Type: Grant
    Filed: September 10, 2008
    Date of Patent: April 19, 2011
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Akiya Kawaue, Takeshi Iwai, Hideo Hada, Shinichi Hidesaka, Tsuyoshi Kurosawa, Natsuko Maruyama, Kensuke Matsuzawa, Takehiro Seshimo, Hiroaki Shimizu, Tsuyoshi Nakamura
  • Patent number: 7919227
    Abstract: A positive resist composition including a resin component (A) which exhibits increased alkali solubility under action of acid and an acid-generator component (B) which generates acid upon exposure, the resin component (A) including a structural unit (a1) represented by general formula (I) shown below: wherein R represents a hydrogen atom, a halogen atom, a lower alkyl group or a halogenated lower alkyl group; R1? represents a hydrogen atom or a lower alkyl group; n represents an integer of 0 to 3; R1 represents a lower alkyl group, a fluorine atom, or a fluorinated lower alkyl group; and p represents an integer of 0 to 2.
    Type: Grant
    Filed: August 7, 2007
    Date of Patent: April 5, 2011
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Yohei Kinoshita, Takeshi Iwai, Toshiyuki Ogata
  • Patent number: 7919226
    Abstract: Sulfonate salts have the formula: CF3—CH(OCOR)—CF2SO3?M+ wherein R is C1-C20 alkyl or C6-C14 aryl, and M+ is a lithium, sodium, potassium, ammonium or tetramethylammonium ion. Onium salts, oximesulfonates and sulfonyloxyimides and other compounds derived from these sulfonate salts are effective photoacid generators in chemically amplified resist compositions.
    Type: Grant
    Filed: August 13, 2008
    Date of Patent: April 5, 2011
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Takeru Watanabe, Takeshi Kinsho, Katsuhiro Kobayashi
  • Patent number: 7914968
    Abstract: A positive resist composition including a resin component (A) and an acid-generator component (B), the resin component (A) including a structural unit (a1) derived from hydroxystyrene, and a structural unit (a2) having an acetal-type acid dissociable dissolution inhibiting group, and the acid-generator component (B) including an acid generator (B1-i) having at least one anion moiety selected from the group consisting of anion moieties represented by general formula (b-3), (b-4), and (b-5), an acid generator (B1-ii) having an anion moiety represented by general formula (b-6) shown below, or an acid generator (B1-iii) having a cation moiety represented by general formula (b?-3) shown below: wherein X? represents an alkylene group of 2 to 6 carbon atoms in which at least one hydrogen atom has been substituted with a fluorine atom; Y? and Z?, U?, V?, and W? each independently represents an alkyl group of 1 to 10 carbon atoms in which at least one hydrogen atom has been substituted with a fluorine atom, [Chem
    Type: Grant
    Filed: June 8, 2007
    Date of Patent: March 29, 2011
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Takeyoshi Mimura, Akiya Kawaue, Ryoichi Takasu
  • Patent number: 7910282
    Abstract: In order to improve a resist pattern shape in a semiconductor lithography process, which is a factor largely affecting on a processing precision, an integration degree and yield, a copolymer for semiconductor lithography where a composition of a hydroxyl group-containing repeating unit in a low molecular weight region is controlled, and a method of producing the same are provided. According to the invention, in a copolymer for semiconductor lithography, which is obtained by copolymerizing a monomer having a hydroxyl group and a monomer having no hydroxyl group, when a copolymer of which composition of a hydroxyl group-containing repeating unit is controlled is used, the object can be achieved.
    Type: Grant
    Filed: April 28, 2005
    Date of Patent: March 22, 2011
    Assignee: Maruzen Petrochemical Co., Ltd.
    Inventors: Takanori Yamagishi, Takayoshi Okada, Satoshi Yamaguchi, Kiyomi Miki
  • Patent number: 7910285
    Abstract: A positive resist composition for immersion exposure including a resin component (A) which has an acid dissociable dissolution inhibiting group and exhibits increased alkali solubility under action of acid and an acid-generator component (B) which generates acid upon exposure, the resin component (A) including a structural unit (a1) derived from an acrylate ester having an acid dissociable, dissolution inhibiting group and a structural unit (a3) derived from an acrylate ester having a polar group-containing aliphatic hydrocarbon group, the amount of the structural unit (a3) based on the combined total of all structural units constituting the resin component (A) being 3 to 12 mol %.
    Type: Grant
    Filed: November 16, 2006
    Date of Patent: March 22, 2011
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventor: Hiroaki Shimizu
  • Patent number: 7902385
    Abstract: Novel ester compounds having formulae (1) to (4) wherein A1 is a polymerizable functional group having a carbon-carbon double bond, A2 is oxygen, methylene or ethylene, R1 is a monovalent hydrocarbon group, R2 is H or a monovalent hydrocarbon group, any pair of R1 and/or R2 may form an aliphatic hydrocarbon ring, R3 is a monovalent hydrocarbon group, and n is 0 to 6 are polymerizable into polymers. Resist compositions comprising the polymers as a base resin are thermally stable and sensitive to high-energy radiation, have excellent sensitivity and resolution, and lend themselves to micropatterning with electron beam or deep-UV.
    Type: Grant
    Filed: July 5, 2007
    Date of Patent: March 8, 2011
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Masaki Ohashi, Takeshi Kinsho, Takeru Watanabe
  • Patent number: 7897321
    Abstract: A monomer, which is represented by General Formula I: wherein, each of R1 and R3 is either —H group or —CH3 group, and R1 and R3 are identical or different to each other; R2 is either a phenyl group or an adamanthyl group; and Q1 is a C1-4 perfluoroalkyl group.
    Type: Grant
    Filed: January 27, 2009
    Date of Patent: March 1, 2011
    Assignee: Fujitsu Limited
    Inventor: Koji Nozaki
  • Patent number: 7887988
    Abstract: A resist composition, which comprises: (A) a resin containing a repeating unit represented by formula (I); and (B) a compound capable of generating an acid upon irradiation with actinic rays or radiation: wherein AR represents a benzene ring or a naphthalene ring; R represents a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group; Z represents a linking group for forming a ring together with AR; and A represents an atom or group selected from the group consisting of a hydrogen atom, an alkyl group, a halogen atom, a cyano group and an alkyloxycarbonyl group, and a pattern forming method using the resist composition.
    Type: Grant
    Filed: March 14, 2007
    Date of Patent: February 15, 2011
    Assignee: FUJIFILM Corporation
    Inventors: Kazuyoshi Mizutani, Kaoru Iwato, Kunihiko Kodama, Masaomi Makino
  • Patent number: 7887990
    Abstract: Disclosed is a fluorine-containing compound represented by formula (1), wherein R1 represents a polymerizable double-bond containing group, R2 represents an acid-labile protecting group, R3 represents a fluorine atom or fluorine-containing alkyl group, and W represents a bivalent linking group. This compound can provide a fluorine-containing polymer compound that has a weight-average molecular weight of 1,000-1,000,000 and contains a repeating unit represented by formula (2), wherein R2, R3 and W are defined as above, each of R4, R5 and R6 independently represents a hydrogen atom, fluorine atom or monovalent organic group, at least two of R4, R5 and R6 may be combined to form a ring. This polymer compound can provide a resist composition capable of forming a pattern that is transparent to exposure light and superior in rectangularity.
    Type: Grant
    Filed: June 11, 2008
    Date of Patent: February 15, 2011
    Assignee: Central Glass Company, Limited
    Inventors: Yoshimi Isono, Jonathan Joachim Jodry, Satoru Narizuka
  • Patent number: 7883827
    Abstract: The present invention provides a planographic printing plate precursor including on a support a photosensitive layer that contains a polymerizable composition containing a specific binder polymer having a repeating unit of formula (I), an infrared absorbent, a polymerization initiator and a polymerizable compound, wherein R1 represents a hydrogen atom or a methyl group; R2 represents a linking group which includes two or more atoms selected from a carbon atom, a hydrogen atom, an oxygen atom, a nitrogen atom and a sulfur atom and has a number of atoms of 2 to 82; A represents an oxygen atom or —NR3— in which R3 represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms; and n represents an integer of 1 to 5. The invention also provides a planographic printing plate precursor provided with a specific photosensitive layer with respect to an alkaline developer.
    Type: Grant
    Filed: April 13, 2007
    Date of Patent: February 8, 2011
    Assignee: FUJIFILM Corporation
    Inventors: Atsushi Sugasaki, Kazuto Kunita, Kazuhiro Fujimaki
  • Patent number: 7879527
    Abstract: A method of forming a positive resist composition of the present invention includes a step (I) of passing a positive resist composition, which is obtained by dissolving a resin component (A) that displays increased alkali solubility under the action of acid and an acid generator component (B) that generates acid upon exposure in an organic solvent (S), through a filter (f1) equipped with a nylon membrane, wherein the resin component (A) is a copolymer containing at least two structural units obtained by polymerizing at least one monomer in the presence of acid. According to the present invention, it is possible to provide a method of producing a positive resist composition, a positive resist composition, and a method of forming a resist pattern that are capable of forming a resist pattern with reduced levels of both bridge-type defects and reprecipitation-type defects.
    Type: Grant
    Filed: May 18, 2006
    Date of Patent: February 1, 2011
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Masaaki Muroi, Kota Atsuchi, Takahiro Nakamura, Masakazu Yamada, Kensuke Saisyo
  • Patent number: 7871752
    Abstract: Lactone-containing compounds having formula (1) are novel wherein R1 is H, F, methyl or trifluoromethyl, R2 and R3 are monovalent hydrocarbon groups, or R2 and R3 may together form an aliphatic hydrocarbon ring, R4 is H or CO2R5, R5 is a monovalent hydrocarbon group, W is CH2, O or S, 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 properties including resolution, pattern edge roughness, pattern density dependency and exposure margin.
    Type: Grant
    Filed: July 26, 2007
    Date of Patent: January 18, 2011
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Koji Hasegawa, Tsunehiro Nishi, Takeshi Kinsho, Seiichiro Tachibana
  • Patent number: 7871753
    Abstract: A positive resist composition of the present invention includes a resin component (A) which displays increased alkali solubility under the action of an acid, and an acid generator component (B) which generates an acid upon exposure, wherein the resin component (A) includes a structural unit (a0) containing a carboxyl group, and at least one structural unit (a1) selected from the group consisting of a structural unit represented by a general formula (a1-2) and a structural unit represented by a general formula (a1-4) shown below: (in the formula, Y represents an aliphatic cyclic group or a lower alkyl group; n represents an integer from 0 to 3; m represents 0 or 1; R represents a hydrogen atom, a halogen atom, a lower alkyl group, or a halogenated lower alkyl group; and R1? and R2? each independently represents a hydrogen atom or a lower alkyl group of 1 to 5 carbon atoms.).
    Type: Grant
    Filed: November 9, 2006
    Date of Patent: January 18, 2011
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Tasuku Matsumiya, Takako Hirosaki
  • Patent number: 7867697
    Abstract: A positive photosensitive composition comprises: (A) 5 to 20 parts by weight of the total amount of at least one compound that generates an acid upon irradiation with an actinic ray; and (B) 100 parts by weight of the total amount of at least one fluorine atom-containing resin having a group that increases a solubility of the resin in an alkaline developer by the action of an acid.
    Type: Grant
    Filed: July 22, 2004
    Date of Patent: January 11, 2011
    Assignee: FUJIFILM Corporation
    Inventor: Kunihiko Kodama
  • Patent number: 7867690
    Abstract: (1) A polymer compound for photoresist compositions which is high in storage stability and small swelling at the development and (2) a compound which is a raw material for such a polymer compound are provided; and (3) a photoresist composition with improved LWR containing the subject polymer compound are further provided. In detail, [1] a tertiary alcohol derivative represented by the following general formula (1) is provided. (In the formula, wherein R1 represents a linear alkyl group having from 1 to 6 carbon atoms, a branched alkyl group having from 3 to 6 carbon atoms or a cyclic alkyl group having from 3 to 6 carbon atoms; R2 represents a hydrogen atom or a methyl group; W represents a linear alkylene group having from 1 to 10 carbon atoms, a branched alkylene group having from 3 to 10 carbon atoms or a cyclic alkylene group having from 3 to 10 carbon atoms; n represents 0 or 1; and p represents 1 or 2.
    Type: Grant
    Filed: February 16, 2007
    Date of Patent: January 11, 2011
    Assignee: Kuraray Co., Ltd.
    Inventors: Osamu Nakayama, Ichihiro Aratani
  • Patent number: 7858286
    Abstract: A positive resist composition and method for forming a resist pattern are provided which enable a resist pattern with excellent shape to be obtained.
    Type: Grant
    Filed: April 7, 2006
    Date of Patent: December 28, 2010
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Yohei Kinoshita, Makiko Irie, Waki Ohkubo, Yusuke Nakagawa, Shinichi Hidesaka
  • Patent number: 7855044
    Abstract: A positive resist composition including a resin component (A) and an acid generator component (B), the resin component (A) including a copolymer (A1) having a structural unit (a1) derived from an acrylate ester having a monocyclic or polycyclic group-containing acid dissociable, dissolution inhibiting group, a structural unit (a2) derived from an acrylate ester having a lactone-containing cyclic group, a structural unit (a3) derived from an acrylate ester having a hydroxyl group and/or cyano group-containing polycyclic group, and a structural unit (a4) represented by general formula (a4-1) shown below: wherein R represents a hydrogen atom, a halogen atom, a lower alkyl group or a halogenated lower alkyl group; R? represents a hydrogen atom, a lower alkyl group or an alkoxy group of 1 to 5 carbon atoms; and f represents 0 or 1.
    Type: Grant
    Filed: June 16, 2006
    Date of Patent: December 21, 2010
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Masaru Takeshita, Hideo Hada, Takeshi Iwai
  • Patent number: 7851140
    Abstract: To provide a resist composition for negative tone development, which can form a pattern having a good profile improved in the pattern undercut and moreover, can reduce the line edge roughness and enhance the in-plane uniformity of the pattern dimension, and a pattern forming method using the same. A resist composition for negative tone development, comprising (A) a resin capable of increasing the polarity by the action of an acid to increase the solubility in a positive tone developer and decrease the solubility in a negative tone developer, (B) a compound capable of generating an acid having an acid dissociation index pKa of ?4.0 or less upon irradiation with an actinic ray or radiation, and (C) a solvent; and a pattern forming method using the same.
    Type: Grant
    Filed: June 12, 2008
    Date of Patent: December 14, 2010
    Assignee: FUJIFILM Corporation
    Inventor: Hideaki Tsubaki
  • Patent number: 7842452
    Abstract: A pattern forming method which uses a positive resist composition comprises: (A) a silicon-free resin capable of increasing its solubility in an alkaline developer under action of an acid; (B) a compound capable of generating an acid upon irradiation with an actinic ray or radiation; (C) a silicon-containing resin having at least one group selected from the group of consisting (X) an alkali-soluble group, (XI) a group capable of decomposing under action of an alkaline developer and increasing solubility of the resin (C) in an alkaline developer, and (XII) a group capable of decomposing under action of an acid and increasing solubility of the resin (C) in an alkaline developer, and (D) a solvent, the method comprising: (i) a step of applying the positive resist composition to a substrate to form a resist coating, (ii) a step of exposing the resist coating to light via an immersion liquid, (iii) a step of removing the immersion liquid remaining on the resist coating, (iv) a step of heating the resist coating, a
    Type: Grant
    Filed: December 9, 2008
    Date of Patent: November 30, 2010
    Assignee: Fujifilm Corporation
    Inventors: Shinichi Kanna, Haruki Inabe, Hiromi Kanda
  • Patent number: 7838199
    Abstract: The invention relates to new polymers that comprise units that contain one or more photoacid generator groups and photoresists that contain the polymers. Preferred polymers of the invention are suitable for use in photoresists imaged at short wavelengths such as sub-250 nm or sub-200 nm, particularly 248 nm and 193 nm.
    Type: Grant
    Filed: February 28, 2008
    Date of Patent: November 23, 2010
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: James W. Thackeray, Roger A. Nassar
  • Patent number: 7838201
    Abstract: A polymer for immersion lithography comprising a repeating unit represented by Formula 1 and a photoresist composition containing the same. A photoresist film formed by the photoresist composition of the invention is highly resistant to dissolution, a photoacid generator in an aqueous solution for immersion lithography, thereby preventing contamination of an exposure lens and deformation of the photoresist pattern by exposure.
    Type: Grant
    Filed: April 8, 2009
    Date of Patent: November 23, 2010
    Assignee: Hynix Semiconductor Inc.
    Inventors: Jae Chang Jung, Cheol Kyu Bok, Chang Moon Lim, Seung Chan Moon
  • Patent number: 7833694
    Abstract: Lactone-containing compounds having formula (1) are novel wherein R1 is H, F, methyl or trifluoromethyl, R2 and R3 are H or monovalent hydrocarbon groups, or R2 and R3 may together form an aliphatic hydrocarbon ring, R4 is H or CO2R5, R5 is a monovalent hydrocarbon group, W is CH2, O or S, and k1 is 3, 4 or 5. 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 properties including resolution, LER, pattern density dependency and exposure margin.
    Type: Grant
    Filed: March 12, 2009
    Date of Patent: November 16, 2010
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Koji Hasegawa, Satoshi Shinachi, Katsuhiro Kobayashi, Tsunehiro Nishi, Takeshi Kinsho
  • Patent number: 7820361
    Abstract: A lithographic printing plate precursor includes: a support; and a photosensitive layer containing (A) an initiator compound, (B) a polymerizable compound and (C) a binder, wherein the photosensitive layer or other layer in contact with the support contains as (D) a component different from the component (C), a copolymer containing (a1) a repeating unit having at least one ethylenically unsaturated bond introduced through an ion pair and (a2) a repeating unit having at least one functional group capable of interacting with a surface of the support.
    Type: Grant
    Filed: August 27, 2007
    Date of Patent: October 26, 2010
    Assignee: FUJIFILM Corporation
    Inventors: Tomoya Sasaki, Hidekazu Oohashi
  • Patent number: 7820369
    Abstract: Polymers containing an acetal or ketal linkage and their use in lithographic photoresist compositions, particularly in chemical amplification photoresists, are provided. The polymer is prepared from at least one first olefinic monomer containing an acetal or ketal linkage, the acid-catalyzed cleavage of which renders the polymer soluble in aqueous base; and at least one second olefinic monomer selected from (i) an olefinic monomer containing a pendant fluorinated hydroxyalkyl group RH, (ii) an olefinic monomer containing a pendant fluorinated alkylsulfonamide group RS, and (iii) combinations thereof. The acetal or ketal linkage may be contained within an acid-cleavable substituent RCL in the first olefinic monomer. A method for using the photoresist compositions containing these polymers in preparing a patterned substrate is also provided in which the polymer is rendered soluble in aqueous base at a temperature of less than about 100° C.
    Type: Grant
    Filed: December 4, 2003
    Date of Patent: October 26, 2010
    Assignee: International Business Machines Corporation
    Inventors: Robert David Allen, Gregory Breyta, Phillip Joe Brock, Richard Anthony DiPietro, Ratnam Sooriyakumaran, Hoa D. Truong, Gregory Michael Wallraff
  • Patent number: 7816066
    Abstract: A positive resist composition includes a resin component (A), and an acid generator component (B) which generates an acid upon exposure and includes an acid generator (B1) represented by general formula (B1): (wherein R51 represents a straight chain, branched chain, or cyclic alkyl group, or a straight chain, branched chain, or cyclic fluorinated alkyl group; R52 represents a hydrogen atom, a hydroxyl group, a halogen atom, a straight chain, branched chain, or cyclic alkyl group, a straight chain or branched chain halogenated alkyl group, or a straight chain or branched chain alkoxy group; R53 represents an aryl group which may include a substituent; and n represents an integer from 1 to 3).
    Type: Grant
    Filed: April 7, 2006
    Date of Patent: October 19, 2010
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventor: Yohei Kinoshita
  • Patent number: 7811742
    Abstract: A lithographic printing plate precursor includes: a support; and a photosensitive layer containing a binder polymer containing a positively charged nitrogen atom in at least one of a main chain and a side chain of the binder polymer, a compound containing an ethylenically unsubstituted bond; and a radical polymerization initiator.
    Type: Grant
    Filed: February 22, 2008
    Date of Patent: October 12, 2010
    Assignee: FUJIFILM Corporation
    Inventors: Yoshinori Taguchi, Keiichi Adachi, Shigekatsu Fujii
  • Patent number: 7803513
    Abstract: A chemically amplified resist composition comprising: (A) a salt represented by the formula (I): wherein R21 represents a C1-C30 hydrocarbon group etc., Q1 and Q2 each independently represent a fluorine atom etc., and A+ represents at least one organic cation selected from a cation represented by the formula (Ia): wherein P1, P2 and P3 each independently represent a C1-C30 alkyl group etc., a cation represented by the formula (Ib): wherein P4 and P5 each independently represent a hydrogen atom etc., and a cation represented by the formula (Ic): wherein P10, P11, P12, P13, P14, P15, P16, P17, P18, P19, P20 and P21 each independently represent a hydrogen atom etc.
    Type: Grant
    Filed: March 19, 2008
    Date of Patent: September 28, 2010
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Satoshi Yamaguchi, Yoshiyuki Takata, Kaoru Araki
  • Patent number: 7803512
    Abstract: A positive resist composition that includes a resin component (A) that exhibits increased alkali solubility under the action of acid, and an acid generator component (B) that generates acid on exposure to radiation, wherein the component (A) includes a structural unit (a1) represented by a general formula (a1-2) or (a1-4), a structural unit (a2) derived from an acrylate ester that contains a lactone-containing monocyclic or polycyclic group, and a structural unit (a3), which is different from the structural unit (a1) and the structural unit (a2), and is derived from an acrylate ester that contains an aliphatic cyclic group-containing non-acid-dissociable, dissolution-inhibiting group and contains no polar groups, and the component (B) includes an onium salt (B1) having an anion portion represented by a formula: R41—SO3?.
    Type: Grant
    Filed: December 13, 2005
    Date of Patent: September 28, 2010
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Yohei Kinoshita, Isao Hirano
  • Patent number: 7803519
    Abstract: A method for manufacturing a semiconductor device using a photoresist polymer comprising a fluorine component, a photoresist composition containing the photoresist polymer and an organic solvent to reduce surface tension, by forming a photoresist film uniformly on the whole surface of an underlying layer pattern to allow a subsequent ion-implanting process to be stably performed.
    Type: Grant
    Filed: April 8, 2009
    Date of Patent: September 28, 2010
    Assignee: Hynix Semiconductor Inc.
    Inventor: Jae Chang Jung
  • Patent number: 7799507
    Abstract: A positive resist composition for immersion lithography of the present invention includes a resin component (A) which exhibits increased alkali solubility under the action of acid; and an acid generator component (B) which generates acid on exposure, wherein the resin component (A) includes a cyclic main chain resin (A1) containing a fluorine atom and no acid-dissociable group, and a resin (A2) containing a structural unit (a) derived from an acrylic acid and no fluorine atom.
    Type: Grant
    Filed: April 23, 2007
    Date of Patent: September 21, 2010
    Assignee: Tokyo Ohka Co., Ltd.
    Inventors: Kotaro Endo, Makiko Irie, Takeshi Iwai, Yoshiyuki Utsumi, Yasuhiro Yoshii, Tsuyoshi Nakamura
  • Patent number: 7799505
    Abstract: The invention is related to an arylsulfonium salt compound having a polycyclic hydrocarbon structure in a cation moiety.
    Type: Grant
    Filed: October 23, 2007
    Date of Patent: September 21, 2010
    Assignee: FUJIFILM Corporation
    Inventors: Kunihiko Kodama, Tomotaka Tsuchimura, Hiroshi Saegusa, Hideaki Tsubaki
  • Patent number: 7794914
    Abstract: The present invention provides a chemically amplified resist composition comprising: a resin (A) which contains no fluorine atom and a structural unit (a1) having an acid-labile group, a resin (B) which contains a structural unit (b2) having a fluorine-containing group and at least one structural unit selected from a structural unit (b1) having an acid-labile group, a structural unit (b3) having a hydroxyl group and a structural unit (b4) having a lactone structure, and an acid generator.
    Type: Grant
    Filed: February 12, 2007
    Date of Patent: September 14, 2010
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Nobuo Ando, Yusuke Fuji, Ichiki Takemoto
  • Patent number: 7794913
    Abstract: A chemically amplified positive resist composition comprising (A) a resin which comprises (i) a polymerization unit represented by the formula (I): (ii) a polymerization unit represented by the formula (II): and (iii) at least one polymerization unit selected from the group consisting of a polymerization unit represented by the formula (III): and a polymerization unit represented by the formula (IV): and (B) at least one acid generator.
    Type: Grant
    Filed: May 15, 2008
    Date of Patent: September 14, 2010
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Makoto Akita, Masumi Suetsugu, Kazuhiko Hashimoto
  • Patent number: 7794916
    Abstract: A polymer compound having a structure represented by the formula (1) as defined herein at a main chain terminal, and a positive photosensitive composition containing a polymer compound having a structure represented by the following formula (1) as defined herein at a main chain terminal and a photoacid generator capable of generating an acid upon irradiation with actinic rays or radiation.
    Type: Grant
    Filed: November 21, 2007
    Date of Patent: September 14, 2010
    Assignee: FUJIFILM Corporation
    Inventor: Akinori Shibuya
  • Patent number: 7781144
    Abstract: The present invention is a positive resist composition and a resist pattern forming method including a resin component (A) which has a polymer compound (A1) having a structural units (a1) including an acetal type acid dissociable, dissolution inhibiting group, a structural unit (a2) derived from an acrylate ester having a lactone-containing polycyclic group, and a structural unit (a3) derived from an acrylate ester having a polar group-containing aliphatic hydrocarbon group, and an acid generator component (B) having an onium salt-based acid generator (B1) having a cation portion represented by a general formula (b-1) shown below [wherein, R11 represents an alkyl group, an alkoxy group, a halogen atom or a hydroxyl group; R12 to R13 each represents, independently, an aryl group or the alkyl group that may have substituent group; n? represents either 0 or an integer from 1 to 3].
    Type: Grant
    Filed: April 18, 2006
    Date of Patent: August 24, 2010
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Yohei Kinoshita, Waki Ohkubo, Yusuke Nakagawa, Shinichi Hidesaka, Makiko Irie
  • Patent number: 7776510
    Abstract: A compound represented by general formula (b-14); and acid generator consisting of the compound; and a resist composition including a base component (A) which exhibits changed solubility in an alkali developing solution under action of acid and an acid-generator component (B) which generates acid upon exposure, the acid-generator component (B) including an acid generator (B1) consisting of a compound represented by general formula (b1-14): wherein R7? to R9? each independently represents an aryl group or an alkyl group, wherein two of R7? to R9? may be bonded to each other to form a ring with the sulfur atom, and at least one of R7? to R9? represents a substituted aryl group in which a portion or all of the hydrogen atoms are substituted with an alkoxyalkyloxy group or an alkoxycarbonylalkyloxy group; and X? represents an anion.
    Type: Grant
    Filed: June 9, 2008
    Date of Patent: August 17, 2010
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Takeshi Iwai, Hideo Hada, Keita Ishiduka, Akiya Kawaue, Hiroaki Shimizu, Kyoko Ohshita, Tsuyoshi Nakamura, Komei Hirahara, Yuichi Suzuki, Takehiro Seshimo
  • Patent number: 7776511
    Abstract: A positive resist composition including a resin component (A) which exhibits increased alkali solubility under action of acid and an acid-generator component (B) which generates acid upon exposure, the resin component (A) including a structural unit (a0-1) represented by general formula (a0-1) shown below and a structural unit (a0-2) represented by general formula (a0-2) shown below: wherein: R represents a hydrogen atom, a halogen atom, a lower alkyl group or a halogenated lower alkyl group; each of Y1 and Y3 independently represents an aliphatic cyclic group; Z represents a tertiary alkyl group-containing group or an alkoxyalkyl group; a represents an integer of 1 to 3, and b represents an integer of 0 to 2, such that a+b=1 to 3; each of c, d and e independently represents an integer of 0 to 3; each of g and h independently represents an integer of 0 to 3; and i represents an integer of 1 to 3.
    Type: Grant
    Filed: May 18, 2007
    Date of Patent: August 17, 2010
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Masaru Takeshita, Ryoji Watanabe
  • Patent number: 7771912
    Abstract: A positive resist composition comprises: (A) a resin of which solubility in an alkali developer increases under the action of an acid, (B) a compound capable of generating an acid upon irradiation with actinic rays or radiation, (C) a resin having at least one repeating unit selected from fluorine atom-containing repeating units represented by the following formulae (1-1), (1-2) and (1-3), the resin being stable to an acid and insoluble in an alkali developer, and (D) a solvent: wherein R1 represents a hydrogen atom or an alkyl group; R2 represents a fluoroalkyl group; R3 represents a hydrogen atom or a monovalent organic group; R4 to R7 each independently represents a hydrogen atom, a fluorine atom, an alkyl group, a fluoroalkyl group, an alkoxy group or a fluoroalkoxy group, provided that at least one of R4 to R7 represents a fluorine atom, and R4 and R5, or R6 and R7 may combine to form a ring; R8 represents a hydrogen atom, a fluorine atom or a monovalent organic group; Rf represents a fluorine atom
    Type: Grant
    Filed: December 11, 2006
    Date of Patent: August 10, 2010
    Assignee: FUJIFILM Corporation
    Inventors: Kei Yamamoto, Shinichi Kanna, Hiromi Kanda
  • Patent number: 7771913
    Abstract: There is disclosed a resist composition comprising, at least, a polymer including repeating units represented by the following general formula (1). There can be provided a resist composition that has a good barrier property against water, prevents resist components from leaching to water, has high receding contact angle against water, does not require a protective film, has an excellent process applicability, suitable for the liquid immersion lithography and makes it possible to form micropatterns with high precision.
    Type: Grant
    Filed: March 30, 2007
    Date of Patent: August 10, 2010
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Tatsushi Kaneko, Jun Hatakeyama, Yuji Harada
  • Patent number: 7771914
    Abstract: A resist composition comprises a polymer comprising recurring units having formula (1) wherein R1, R4, R7, and R14 are H or methyl, R2, R3, R15, and R16 are H, alkyl or fluoroalkyl, R is F or H, R5 is alkylene, R6 is fluorinated alkyl, R8 is a single bond or alkylene, R10 and R11 are H, F, methyl or trifluoromethyl, R12 and R13 are a single bond, —O— or —CR18R19—, R9, R18, and R19 are H, F, methyl or trifluoromethyl, R17 is alkylene, X1, X2 and X3 are —C(?O)—O—, —O—, or —C(?O)—R20—C(?O)—O— wherein R20 is alkylene, 0?(a-1)<1, 0?(a-2)<1, 0?(a-3)<1, 0<(a-1)+(a-2)+(a-3)<1, 0<b<1, and 0<(a-1)+(a-2)+(a-3)+b?1.
    Type: Grant
    Filed: October 16, 2007
    Date of Patent: August 10, 2010
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Takao Yoshihara, Yuji Harada, Wataru Kusaki
  • Patent number: 7767378
    Abstract: A method for producing a resist composition including a resin component (A) that exhibits changed alkali solubility under the action of acid and an acid generator component (B) that generates acid upon exposure, the method including the steps of: obtaining the component (A) by mixing a plurality of copolymers, which are composed of the same structural units but have mutually different measured values for the contact angle.
    Type: Grant
    Filed: November 4, 2005
    Date of Patent: August 3, 2010
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hiroaki Shimizu, Masaru Takeshita
  • Patent number: 7767379
    Abstract: There is provided a positive resist composition including a resin component (A) which displays increased solubility in an alkali developing solution under action of acid, and an acid generator component (B) which generates an acid upon exposure, wherein the resin component (A) includes a polymer compound (A1) containing a structural unit (a0) represented by a general formula (a0-1) shown below, and a structural unit (a1) derived from an acrylate ester which has an acid dissociable, dissolution inhibiting group: (in the formula (a0-1), R represents a hydrogen atom, a lower alkyl group, or a halogenated lower alkyl group; two of R? each independently represents a hydrogen atom, a lower alkyl group, or an alkoxy group of 1 to 5 carbon atoms; X represents an alkylene group of 1 to 5 carbon atoms, an oxygen atom, or a sulfur atom.).
    Type: Grant
    Filed: September 4, 2008
    Date of Patent: August 3, 2010
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Takahiro Dazai, Takayoshi Mori, Hiroaki Shimizu, Kyoko Oshita
  • Patent number: 7767377
    Abstract: The present invention is a positive type resist composition comprising a resin component (A) for use in a resist, having alkali solubility which increases under the action of an acid, an acid generator component (B) which generates an acid upon being exposed, and an organic solvent which dissolves the resin component (A) and the acid generator component (B), wherein the resin component (A) contains the resin component (A1) for use in a resist having alkali solubility which increases under the action of an acid having the following structural units (a1), (a2) and (a3): structural unit (a1): a structural unit derived from an (?-lower alkyl) acrylic ester which contains acid-dissociable, dissolution-inhibiting groups expressed by the following general formula (1): [chemical formula 1] (in formula (1), R represents a hydrogen atom or a lower alkyl group, R11represents acid-dissociable, dissolution-inhibiting groups consisting of chain tertiary alkyl groups), structural unit (a2): a structural unit deriv
    Type: Grant
    Filed: April 19, 2005
    Date of Patent: August 3, 2010
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Shinichi Kohno, Takeshi Iwai, Ryotaro Hayashi
  • Patent number: 7763412
    Abstract: A polymer, a positive resist composition, and a method for forming a resist pattern that are able to form a resist pattern with a high level of resolution and excellent etching resistance. The present invention uses a polymer that contains a structural unit (a1) represented by a general formula (a-1) shown below and a structural unit (a2) represented by a general formula (a-2) shown below, another polymer that contains the structural unit (a1) and a structural unit (a3) represented by a general formula (a-3) shown below, and another polymer that contains the structural unit (a1), the structural unit (a2), and the structural unit (a3).
    Type: Grant
    Filed: June 2, 2005
    Date of Patent: July 27, 2010
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Masaru Takeshita, Hideo Hada, Ryotaro Hayashi, Takeshi Iwai, Syogo Matsumaru, Satoshi Fujimura
  • Patent number: 7759045
    Abstract: A chemically amplified positive resist composition comprising (A) a salt represented by the formula (I): A+?O3S—R??(I) wherein R represents a 9,10-anthraquinonyl group which may be substituted with at least one group selected from the group consisting of a C1-C4 alkyl group, a C1-C4 alkoxy group and a hydroxyl group, and the C1-C4 alkyl group and the C1-C4 alkoxy group may be substituted, and A+ represents an organic counter cation, and (B) a resin which contains a structural unit which has an acid-labile group and which itself is insoluble or poorly soluble in an aqueous alkali solution but becomes soluble in an aqueous alkali solution by the action of an acid.
    Type: Grant
    Filed: June 24, 2008
    Date of Patent: July 20, 2010
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Makoto Akita, Isao Yoshida, Yukako Harada
  • Patent number: 7749680
    Abstract: A photoresist composition includes a base resin, a copolymer of acrylic acid or methacrylic acid and 3,3-dimethoxypropene, a photoacid generator, an organic base, and an organic solvent, and is used for forming a fine (micro) pattern in a semiconductor device by double patterning. The invention method can markedly reduce the number of steps in etching and hard mask deposition processes, so that work hours and manufacturing costs may be reduced, contributing to an increase in yield of semiconductor devices.
    Type: Grant
    Filed: June 26, 2007
    Date of Patent: July 6, 2010
    Assignee: Hynix Semiconductor Inc.
    Inventors: Jae Chang Jung, Sung Koo Lee
  • Patent number: 7745097
    Abstract: There are provided a novel compound represented by a general formula (b1-1) shown below, which is useful as an acid generator for a resist composition and a manufacturing method thereof, a compound useful as a precursor of the novel compound and a manufacturing method thereof, an acid generator, a resist composition and a method of forming a resist pattern.
    Type: Grant
    Filed: July 16, 2008
    Date of Patent: June 29, 2010
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hideo Hada, Takeshi Iwai, Takehiro Seshimo, Akiya Kawaue, Keita Ishiduka
  • Patent number: RE41580
    Abstract: A novel lactone-containing compound is provided as well as a polymer comprising units of the compound. The polymer is used as a base resin to formulate a resist composition having a high sensitivity, resolution and etching resistance.
    Type: Grant
    Filed: September 23, 2005
    Date of Patent: August 24, 2010
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Koji Hasegawa, Tsunehiro Nishi, Takeshi Kinsho, Jun Hatakeyama, Osamu Watanabe