Polymer Of Unsaturated Acid Or Ester Patents (Class 430/910)
  • 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
  • Patent number: 8795942
    Abstract: There is disclosed a resist composition that remarkably improves the resolution of photolithography using a high energy beam such as ArF excimer laser light as a light source, and exhibits excellent resistance to surface roughness and side lobe under use of a halftone phase shift mask; and a patterning process using the resist composition. The positive resist composition at least comprises (A) a resin component comprising a repeating unit represented by the following general formula (1); (B) a photoacid generator generating sulfonic acid represented by the following general formula (2) upon exposure to a high energy beam; and (C) an onium salt where a cation is sulfonium represented by the following general formula (3), or ammonium represented by the following general formula (4); and an anion is represented by any one of the following general formulae (5) to (7).
    Type: Grant
    Filed: December 11, 2007
    Date of Patent: August 5, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Tomohiro Kobayashi, Youichi Ohsawa, Ryosuke Taniguchi
  • Patent number: 8795944
    Abstract: Provided is an actinic ray-sensitive or radiation-sensitive resin composition including: (A) a resin capable of increasing the solubility in an alkali developer by the action of an acid, (B) a compound capable of generating an acid upon irradiation with an actinic ray or radiation, and (C) a resin which contains (c) a repeating unit having at least one polarity conversion group and has at least either a fluorine atom or a silicon atom.
    Type: Grant
    Filed: December 11, 2009
    Date of Patent: August 5, 2014
    Assignee: FUJIFILM Corporation
    Inventors: Hiroshi Saegusa, Kaoru Iwato, Shuji Hirano, Yusuke Iizuka
  • Patent number: 8790868
    Abstract: A method of forming a resist pattern, the method including: forming a resist film on a substrate using a resist composition containing a base component (A) that exhibits reduced solubility in an organic solvent under the action of acid, an acid generator component (B) that generates acid upon exposure and a fluorine-containing polymeric compound (F), exposing the resist film, and patterning the resist film by negative tone development using a developing solution containing the organic solvent, thereby forming a resist pattern, wherein the base component (A) contains a resin component (A1) containing a structural unit (a1) derived from an acrylate ester, the dissolution rates of (A1) and (F) in the developing solution are each at least 10 nm/s, and the absolute value of the difference in the dissolution rates of (A1) and (F) in the developing solution is not more than 80 nm/s.
    Type: Grant
    Filed: April 26, 2012
    Date of Patent: July 29, 2014
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hiroaki Shimizu, Hideto Nito
  • Patent number: 8790860
    Abstract: An actinic ray-sensitive or radiation-sensitive resin composition capable of forming a hole pattern which has an ultrafine pore diameter (for example, 60 nm or less) and has an excellent cross-sectional shape with excellent local pattern dimensional uniformity; and a resist film, a pattern forming method, a method for preparing an electronic device, and an electronic device, each using the same, are provided.
    Type: Grant
    Filed: September 11, 2012
    Date of Patent: July 29, 2014
    Assignee: FUJIFILM Corporation
    Inventors: Kosuke Koshijima, Hidenori Takahashi, Shuhei Yamaguchi, Kei Yamamoto
  • Patent number: 8791288
    Abstract: An acid-labile ester monomer of spirocyclic structure has formula (1) wherein Z is a monovalent group having a polymerizable double bond, X is a divalent group which forms a cyclopentane, cyclohexane or norbornane ring, R2 is H or monovalent hydrocarbon, R3 and R4 are H or monovalent hydrocarbon, or R3 and R4, taken together, stand for a divalent group which forms a cyclopentane or cyclohexane ring, and n is 1 or 2. A polymer obtained from the acid-labile ester monomer has so high reactivity in acid-catalyzed elimination reaction that the polymer may be used to formulate a resist composition having high resolution.
    Type: Grant
    Filed: May 25, 2010
    Date of Patent: July 29, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takeshi Kinsho, Tomohiro Kobayashi, Masayoshi Sagehashi, Takeru Watanabe, Koji Hasegawa, Seiichiro Tachibana
  • Patent number: 8790861
    Abstract: A monomer has the Formula I: wherein R1, R2, and R3 are each independently a C1-30 monovalent organic group, and R1, R2, and R3 are each independently unsubstituted or include a halogen, nitrile, ether, ester, ketone, alcohol, or a combination comprising at least one of the foregoing functional groups; R4 includes H, F, C1-4 alkyl, or C1-4 fluoroalkyl; A is a single bond or a divalent linker group, wherein A is unsubstituted or substituted to include a halogen, nitrile, ether, ester, ketone, alcohol, or a combination comprising at least one of the foregoing functional groups; m and n are each independently an integer of 1 to 8; and x is 0 to 2n+2, and y is 0 to 2m+2.
    Type: Grant
    Filed: December 21, 2012
    Date of Patent: July 29, 2014
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: Cong Liu, Mingqi Li, Cheng-Bai Xu
  • 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
  • Patent number: 8778595
    Abstract: A resist composition containing a base component (A) which generates acid upon exposure, and exhibits changed solubility in a developing solution under the action of acid, wherein the base component (A) contains a polymeric compound (A1) having a structural unit (a5) represented by general formula (a5-0) shown below and a structural unit (a6) that generates acid upon exposure. In the formula, 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, R1 represents a sulfur atom or an oxygen atom, R2 represents a single bond or a divalent linking group, and Y represents a hydrocarbon group in which a carbon atom or a hydrogen atom may be substituted with a substituent.
    Type: Grant
    Filed: November 16, 2012
    Date of Patent: July 15, 2014
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Daichi Takaki, Daiju Shiono, Yoshiyuki Utsumi, Jun Iwashita
  • Patent number: 8778594
    Abstract: A resist composition having a resin having a structural unit represented by the formula (I), a resin being insoluble or poorly soluble in alkali aqueous solution, but becoming soluble in an alkali aqueous solution by the action of an acid and not including the structural unit represented by the formula (I), an acid generator, and a compound represented by the formula (II), wherein R1, A1, A13, A14, X12, R23, R24, R25, R26, X21 and X22 are defined in the specification.
    Type: Grant
    Filed: July 18, 2012
    Date of Patent: July 15, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Hiromu Sakamoto, Yuichi Mukai
  • Patent number: 8771921
    Abstract: A negative resist composition including an alkali-soluble resin component (A), an acid generator component (B) that generates acid upon exposure, and a cross-linking component (C), the alkali-soluble resin component (A) including a polymeric compound (F) having a structural unit (f1) containing a base dissociable group and a structural unit (f2) containing a cross-linking group-containing group.
    Type: Grant
    Filed: March 2, 2012
    Date of Patent: July 8, 2014
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Abe Sho, Shiono Daiju, Hirano Tomoyuki, Dazai Takahiro
  • 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
  • Patent number: 8771916
    Abstract: An actinic ray-sensitive or radiation-sensitive resin composition, includes: (A) a resin capable of increasing the solubility of the resin (A) in an alkali developer by the action of an acid; and (C) a resin having at least either a fluorine atom or a silicon atom and containing (c) a repeating unit having at least two or more polarity conversion groups.
    Type: Grant
    Filed: December 11, 2009
    Date of Patent: July 8, 2014
    Assignee: FUJIFILM Corporation
    Inventors: Shuji Hirano, Kaoru Iwato, Hiroshi Saegusa, Yusuke Iizuka
  • Patent number: 8765358
    Abstract: A water-soluble resin composition for forming fine patterns comprising water-soluble polymer represented by Chemical Formula 1 as below and the first water-soluble solvent, is coated and heated on a photoresist layer having at least one contact hole to reduce a size of the at least one contact hole. (In Chemical Formula 1, each of R1, R2, R3 and R5 independently represents an alkyl group of C1-30 or an cyclo alkyl group of C3-30 which respectively have one selected from the group consisting of hydrogen, an ether group, an ester group, a carbonyl group, an acetal, an epoxy group, a nitril group, an amine group, and an aldehyde group; each of R4, R6, R7 and R8 independently represents hydrogen or a methyl group; n represents an integer of 0 to 5; a represents a real number of 0.05 to 0.5; each of b, c and d respectively represents a real number of 0 to 0.7; and a+b+c+d=1).
    Type: Grant
    Filed: June 29, 2011
    Date of Patent: July 1, 2014
    Assignee: Korea Kumho Petrochemical Co., Ltd.
    Inventors: Sang Wook Park, So Jung Park, Dong-Chul Seo
  • Patent number: 8765353
    Abstract: A resist composition includes: a crosslinking material that is crosslinked in the presence of an acid; an acid amplifier; and a solvent.
    Type: Grant
    Filed: September 21, 2011
    Date of Patent: July 1, 2014
    Assignee: Sony Corporation
    Inventors: Koji Arimitsu, Nobuyuki Matsuzawa, Isao Mita
  • Patent number: 8758974
    Abstract: A method is described for the direct photochemical modification and micro-patterning of polymer surfaces, without the need to use a photoresist. For example, micropatterns of various functional chemical groups, biomolecules, and metal films have been deposited on poly(carbonate) and poly(methyl methacrylate) surfaces. These patterns may be used, for example, in integrated electronics, capture elements, or sensing elements in micro-fluidic channels.
    Type: Grant
    Filed: December 12, 2003
    Date of Patent: June 24, 2014
    Assignee: Board of Supervisors of Louisiana State University And Agricultural and Mechanical College
    Inventors: Steven A. Soper, Robin L. McCarley, Bikas Vaidya
  • 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: 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: 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: 8741543
    Abstract: A resist composition having a resin having a structural unit represented by the formula (I), a resin being insoluble or poorly soluble in alkali aqueous solution, but becoming soluble in an alkali aqueous solution by the action of an acid and not including the structural unit represented by the formula (I), and an acid generator having an acid labile group, wherein R1, A1, A13, A14, X12 are defined in the specification.
    Type: Grant
    Filed: July 18, 2012
    Date of Patent: June 3, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Satoshi Yamaguchi, Yuki Suzuki
  • Patent number: 8735046
    Abstract: A polymer obtained from copolymerization of a recurring unit having a carboxyl group and/or phenolic hydroxyl group substituted with an acid labile group with a methacrylate having a phenolic hydroxyl-bearing pyridine is useful as a base resin in a positive resist composition. The resist composition comprising the polymer is improved in contrast of alkali dissolution rate before and after exposure, acid diffusion control, resolution, and profile and edge roughness of a pattern after exposure.
    Type: Grant
    Filed: November 21, 2011
    Date of Patent: May 27, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Koji Hasegawa
  • Patent number: 8735044
    Abstract: A salt represented by the formula (a): wherein Q1 and Q2 each independently represent a fluorine atom etc., X1 represents a single bond etc., X2 represents a single bond etc., Y1 represents a C3-C6 alicyclic hydrocarbon group etc., with the proviso that —X2—Y1 group has one or more fluorine atoms, and Z+ represents an organic counter cation, and a photoresist composition comprising the salt represented by the formula (a) and a resin comprising a structural unit having an acid-labile group and being insoluble or poorly soluble in an aqueous alkali solution but becoming soluble in an aqueous alkali solution by the action of an acid.
    Type: Grant
    Filed: May 25, 2010
    Date of Patent: May 27, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Isao Yoshida
  • Patent number: 8735047
    Abstract: A resist composition having a resin having a structural unit represented by the formula (I), a resin being insoluble or poorly soluble in alkali aqueous solution, but becoming soluble in an alkali aqueous solution by the action of an acid and not including the structural unit represented by the formula (I), and an acid generator represented by the formula (II), wherein R1, A1, A13, A14, X12, Q1, Q2, L1, ring W1 and Z+ are defined in the specification.
    Type: Grant
    Filed: July 18, 2012
    Date of Patent: May 27, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Satoshi Yamaguchi
  • Patent number: 8728707
    Abstract: A resist composition having a resin having a structural unit represented by the formula (I), a resin being insoluble or poorly soluble in alkali aqueous solution, but becoming soluble in an alkali aqueous solution by the action of an acid and not including the structural unit represented by the formula (I), an acid generator, and a compound represented by the formula (II), wherein R1, A1, A13, A14, X12, R23 and ring W21 are defined in the specification.
    Type: Grant
    Filed: July 18, 2012
    Date of Patent: May 20, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Satoshi Yamaguchi
  • Patent number: 8722825
    Abstract: A polymer comprises the polymerized product of monomers comprising a nitrogen-containing monomer comprising formula (Ia), formula (Ib), or a combination of formulas (Ia) and (Ib), and an acid-deprotectable monomer having the formula (II): wherein a is 0 or 1, each Ra is independently H, F, C1-10 alkyl, or C1-10 fluoroalkyl, L1 is a straight chain or branched C1-20 alkylene group, or a monocyclic, polycyclic, or fused polycyclic C3-20 cycloalkylene group, each Rb is independently H, C1-10 alkyl, C3-20 cycloalkyl, C3-20 heterocycloalkyl, an aliphatic C5-20 oxycarbonyl, or a C1-30 acyl group optionally including a heteroatom substituent group, where each Rb is separate or at least one Rb is attached to an adjacent Rb; LN is a nitrogen-containing monocyclic, polycyclic, or fused polycyclic C3-20 heterocycloalkylene group, and X is H, C1-10 alkyl, aliphatic C5-20 oxycarbonyl, or a C1-30 acyl group optionally including a heteroatom substituent group; and each Rc is independently C1-10 alkyl, C3-20 cycloalkyl, o
    Type: Grant
    Filed: May 29, 2012
    Date of Patent: May 13, 2014
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: Deyan Wang, Chunyi Wu, Cong Liu, Gerhard Pohlers, Cheng-bai Xu, George G. Barclay
  • Patent number: 8722306
    Abstract: A radiation-sensitive resin composition includes a resin (A1) that includes a repeating unit shown by the following formula (1-1) and a repeating unit shown by the following formula (1-2), and a radiation-sensitive acid generator (B). The radiation-sensitive resin composition exhibits excellent sensitivity, and can reduce a mask error factor (MEEF). wherein R1, R2, and R3 individually represent a linear or branched alkyl group having 1 to 4 carbon atoms, R4 represents a hydrogen atom, a linear or branched alkyl group having 2 to 4 carbon atoms, a linear or branched fluoroalkyl group having 1 to 4 carbon atoms, or a linear or branched alkoxy group having 1 to 4 carbon atoms, and q represents an integer from 0 to 3.
    Type: Grant
    Filed: May 26, 2008
    Date of Patent: May 13, 2014
    Assignee: JSR Corporation
    Inventors: Hirokazu Sakakibara, Makoto Shimizu, Takehiko Naruoka, Tomoki Nagai, Yoshifumi Oizumi
  • Patent number: 8715919
    Abstract: Lithography methods on a semiconductor substrate are described. The methods include coating a resist layer on the substrate, wherein the resist layer comprises a resist polymer configured to turn soluble to a base solution in response to reaction with an acid, and a switchable polymer that includes a base soluble polymer having a carboxylic acid, hydroxyl, lactone, or anhydride functional group, performing a pre-exposure bake on the resist layer, exposing the resist-coated substrate, and developing the exposed substrate with a developing solution.
    Type: Grant
    Filed: August 20, 2013
    Date of Patent: May 6, 2014
    Assignee: Taiwan Semiconductor Manufacturing Company, Ltd.
    Inventors: Ching-Yu Chang, Chih-Cheng Chiu
  • Patent number: 8715918
    Abstract: Thick film photoresist compositions are disclosed.
    Type: Grant
    Filed: September 25, 2007
    Date of Patent: May 6, 2014
    Assignee: AZ Electronic Materials USA Corp.
    Inventors: Medhat A. Toukhy, Margareta Paunescu
  • Patent number: 8709699
    Abstract: A resist composition having a resin having a structural unit represented by the formula (I), a resin being insoluble or poorly soluble in alkali aqueous solution, but becoming soluble in an alkali aqueous solution by the action of an acid and not including the structural unit represented by the formula (I), and an acid generator represented by the formula (II), wherein R1, A1, A13, A14, X12, Q1, Q2, L1, ring W, Rf1 and Rf2, n and Z+ are defined in the specification.
    Type: Grant
    Filed: July 18, 2012
    Date of Patent: April 29, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Takashi Hiraoka, Mitsuyoshi Ochiai
  • Patent number: 8703383
    Abstract: A copolymer has formula: wherein R1-R5 are independently H, C1-6 alkyl, or C4-6 aryl, R6 is a fluorinated or non-fluorinated C5-30 acid decomposable group; each Ar is a monocyclic, polycyclic, or fused polycyclic C6-20 aryl group; each R7 and R8 is —OR11 or —C(CF3)2OR11 where each R11 is H, a fluorinated or non-fluorinated C5-30 acid decomposable group, or a combination; each R9 is independently F, a C1-10 alkyl, C1-10 fluoroalkyl, C1-10 alkoxy, or a C1-10 fluoroalkoxy group; R10 is a cation-bound C10-40 photoacid generator-containing group, mole fractions a, b, and d are 0 to 0.80, c is 0.01 to 0.80, e is 0 to 0.50 provided where a, b, and d are 0, e is greater than 0, the sum a+b+c+d+e is 1, l and m are integers of 1 to 4, and n is an integer of 0 to 5. A photoresist and coated substrate, each include the copolymer.
    Type: Grant
    Filed: November 17, 2011
    Date of Patent: April 22, 2014
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: James W. Thackeray, Emad Aqad, Su Jin Kang, Owendi Ongayi
  • Patent number: 8697331
    Abstract: A compound is shown by a following formula (1), wherein R1 represents a hydrogen atom, a methyl group, or a trifluoromethyl group, R2 represents a methylene group, an ethylene group, a 1-methylethylene group, a 2-methylethylene group, a divalent alicyclic hydrocarbon group having 4 to 20 carbon atoms, or a derivative thereof, each of R3 represents at least one of a monovalent alicyclic hydrocarbon group having 4 to 20 carbon atoms, a derivative thereof, and a linear or branched alkyl group having 1 to 4 carbon atoms, provided that two of R3 may bond to form a divalent alicyclic hydrocarbon group having 4 to 20 carbon atoms or a derivative thereof together with the carbon atom that is bonded thereto, and X represents a linear or branched fluoroalkylene group having 1 to 20 carbon atoms.
    Type: Grant
    Filed: November 19, 2010
    Date of Patent: April 15, 2014
    Assignee: JSR Corporation
    Inventors: Hirokazu Sakakibara, Takehiko Naruoka, Makoto Shimizu, Yukio Nishimura, Nobuji Matsumura, Yuusuke Asano
  • Patent number: 8697335
    Abstract: A radiation-sensitive resin composition includes a compound, a resin and a radiation-sensitive acid generator. The compound has a structure in which a group represented by a following formula (1) is bound to a nitrogen atom. The resin has an acid-dissociative dissolution-controlling group and has a property such that alkali solubility of the resin increases by an action of an acid. In the formula (1), Y is a monovalent group having 5 to 20 carbon atoms, and “*” represents a bonding hand with the nitrogen atom. In the formula (i), R1, R2 and R3 each independently represent a linear or branched alkyl group having 1 to 4 carbon atoms or a monovalent alicyclic hydrocarbon group having 4 to 12 carbon atoms, or R1 and R2 are linked with each other to form a bivalent alicyclic hydrocarbon group, and “*” represents a bonding hand with the oxygen atom.
    Type: Grant
    Filed: January 17, 2012
    Date of Patent: April 15, 2014
    Assignee: JSR Corporation
    Inventors: Kazuo Nakahara, Mitsuo Sato
  • Patent number: 8697343
    Abstract: An object of the present invention is to provide a novel fluorine-containing polymer, a radiation-sensitive resin composition for liquid immersion lithography which contains the fluorine-containing polymer, which leads to a pattern having an excellent shape and excellent depth of focus, wherein the amount of an eluted component in a liquid for liquid immersion lithography such as water that comes in contact with the resist during exposure in liquid immersion lithography is little, and which provides a larger receding contact angle between the resist film and the liquid for liquid immersion lithography such as water, and a method for purifying the fluorine-containing polymer. The present resin composition comprises a novel fluorine-containing polymer (A) containing repeating units represented by the general formulae (1) and (2) and having Mw of 1,000-50,000, a resin (B) having an acid-unstable group, a radiation-sensitive acid generator (C), a nitrogen-containing compound (D) and a solvent (E).
    Type: Grant
    Filed: March 23, 2007
    Date of Patent: April 15, 2014
    Assignee: JSR Corporation
    Inventors: Hiroki Nakagawa, Hiromitsu Nakashima, Gouji Wakamatsu, Kentarou Harada, Yukio Nishimura, Takeo Shioya
  • Patent number: 8697329
    Abstract: A positive resist composition, which comprises: (A) a resin of which solubility in an alkali developer increases under an 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 of a fluorine atom and a silicon atom; and (D) a solvent, wherein the resin (C) contains at least one of: (C1) a resin having at least one of a fluorine atom and a silicon atom and having an alicyclic structure; and (C2) a resin containing a repeating unit having at least one of a fluorine atom and a silicon atom in a side chain and a repeating unit having an unsubstituted alkyl group in a side chain; and a pattern forming method.
    Type: Grant
    Filed: March 11, 2008
    Date of Patent: April 15, 2014
    Assignee: FUJIFILM Corporation
    Inventors: Hiromi Kanda, Shinichi Kanna
  • Patent number: 8685619
    Abstract: A resist composition having a resin having a structural unit represented by the formula (I), a resin being insoluble or poorly soluble in alkali aqueous solution, but becoming soluble in an alkali aqueous solution by the action of an acid and not including the structural unit represented by the formula (I), and an acid generator represented by the formula (II), wherein R1, A1, A13, A14, X12, R23, R24, R25, X21 and Z1+ are defined in the specification.
    Type: Grant
    Filed: July 18, 2012
    Date of Patent: April 1, 2014
    Assignee: Sumitomo Chemcial Company, Limited
    Inventors: Koji Ichikawa, Yuichi Mukai, Satoshi Yamamoto
  • Patent number: 8685620
    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 base component (A) containing a polymeric compound (A1) having a structural unit (a5) represented by general formula (a5-0) shown below (R1 represents a sulfur atom or an oxygen atom; R2 represents a single bond or a divalent linking group; and Y represents an aromatic hydrocarbon group or an aliphatic hydrocarbon group having a polycyclic group, provided that the aromatic hydrocarbon group or the aliphatic hydrocarbon may have a carbon atom or a hydrogen atom thereof substituted with a substituent.
    Type: Grant
    Filed: November 6, 2012
    Date of Patent: April 1, 2014
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Daichi Takaki, Daiju Shiono, Yoshiyuki Utsumi, Takaaki Kaiho
  • Patent number: 8685618
    Abstract: A resist composition having; (A1) a resin having a structural unit represented by the formula (I), (A2) a resin having a structural unit represented by the formula (II) and being insoluble or poorly soluble in alkali aqueous solution, but becoming soluble in an alkali aqueous solution by the action of an acid and not including the structural unit represented by the formula (I) and (B) an acid generator. wherein R1, A1, A13, X12, A14, R3 and ring X1 are defined in the specification.
    Type: Grant
    Filed: July 18, 2012
    Date of Patent: April 1, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Akira Kamabuchi
  • Patent number: 8679724
    Abstract: A positive resist composition comprises: (A) a resin of which solubility in an alkali developer increases under an 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 of a fluorine atom and a silicon atom; and (D) a solvent; and a pattern forming method using the positive resist composition.
    Type: Grant
    Filed: December 11, 2006
    Date of Patent: March 25, 2014
    Assignee: FUJIFILM Corporation
    Inventors: Hiromi Kanda, Shinichi Kanna
  • Patent number: 8663900
    Abstract: A resist composition having a resin having a structural unit represented by the formula (I), a resin being insoluble or poorly soluble in alkali aqueous solution, but becoming soluble in an alkali aqueous solution by the action of an acid and not including the structural unit represented by the formula (I), and an acid generator represented by the formula (II), wherein R1, A1, A13, A14, X12, RII1, RII2, LII1, YII1, RII3, RII4, RII5, RII6, RII7, n, s and RII8 are defined in the specification.
    Type: Grant
    Filed: July 18, 2012
    Date of Patent: March 4, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Yukako Anryu, Shingo Fujita
  • Patent number: 8663897
    Abstract: According to the present invention, there is provided a polymerizable fluorine-containing sulfonic acid onium salt of the following general formula (2) and a resin obtained by polymerization thereof. It is possible by the use of this sulfonate resin of the present invention to provide a resist composition with high resolution, board depth of focus tolerance (DOF), small line edge roughness (LER) and high sensitivity. In the formula, Z represents a substituted or unsubstituted C1-C6 straight or branched alkylene group, or a divalent moiety in which substituted or unsubstituted C1-C6 straight or branched alkylene groups are bonded in series to a divalent group obtained by elimination of two hydrogen atoms from an alicyclic or aromatic hydrocarbon; R represents a hydrogen atom, a halogen atom, or a C1-C3 alkyl or fluorine-containing alkyl group; and Q+ represents a sulfonium cation or an iodonium cation.
    Type: Grant
    Filed: October 8, 2009
    Date of Patent: March 4, 2014
    Assignee: Central Glass Company, Limited
    Inventors: Takashi Masubuchi, Kazunori Mori, Yuji Hagiwara, Satoru Narizuka, Kazuhiko Maeda
  • Patent number: 8663899
    Abstract: A resist composition having a resin having a structural unit represented by the formula (I), a resin being insoluble or poorly soluble in alkali aqueous solution, but becoming soluble in an alkali aqueous solution by the action of an acid and not including the structural unit represented by the formula (I), and an acid generator, wherein R1, A1, R2, Rb1, Rb2, Lb1, ring Wb1, Rb3, Rb4, and Z1+ are defined in the specification.
    Type: Grant
    Filed: July 18, 2012
    Date of Patent: March 4, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Takashi Hiraoka, Hiromu Sakamoto
  • Patent number: 8658343
    Abstract: A resist composition including a base component (A) which exhibits changed solubility in a developing solution under the action of acid, and an acid generator component (B) which generates acid upon exposure, wherein the base component (A) contains a polymeric compound (A1) having a structural unit (a5) represented by general formula (a5-1). In formula (a5-1), R represents a hydrogen atom, an alkyl group or a halogenated alkyl group, X represents single bond or divalent linking group, W represents a cyclic alkylene group which may include an oxygen atom at arbitrary position, each of Ra and Rb independently represents a hydrogen atom or an alkyl group which may include an oxygen atom at arbitrary position, or alternatively, Ra and Rb may be bonded to each other to form a ring together with the nitrogen atom in the formula, and p represents integer of 1 to 3.
    Type: Grant
    Filed: December 5, 2011
    Date of Patent: February 25, 2014
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Masatoshi Arai, Junichi Tsuchiya, Daiju Shiono, Tomoyuki Hirano, Daichi Takaki
  • Patent number: 8652753
    Abstract: A resist composition having; a resin having a structural unit represented by the formula (I), a resin being insoluble or poorly soluble in alkali aqueous solution, but becoming soluble in an alkali aqueous solution by the action of an acid and not including the structural unit represented by the formula (I), an acid generator, and a salt having an anion represented by the formula (IA). wherein R1, A1, A13, X12, A14, R1A and R2A are defined in the specification.
    Type: Grant
    Filed: July 18, 2012
    Date of Patent: February 18, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Tatsuro Masuyama, Satoshi Yamaguchi
  • Patent number: 8652754
    Abstract: A resist composition having a resin having a structural unit represented by the formula (I), a resin being insoluble or poorly soluble in alkali aqueous solution, but becoming soluble in an alkali aqueous solution by the action of an acid and not including the structural unit represented by the formula (I), and an acid generator represented by the formula (II), wherein R1, A1, R2, Q1 and Q2, L1, ring W, Rf1 and Rf2, n and Z+are defined in the specification.
    Type: Grant
    Filed: July 18, 2012
    Date of Patent: February 18, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Takashi Hiraoka, Mitsuyoshi Ochiai
  • 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
  • Patent number: 8642253
    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: November 8, 2010
    Date of Patent: February 4, 2014
    Assignee: FUJIFILM Incorporated
    Inventor: Hideaki Tsubaki
  • Patent number: 8642245
    Abstract: According to one embodiment, an actinic-ray- or radiation-sensitive resin composition includes a resin that is decomposed when acted on by an acid to thereby increase its solubility in an alkali developer, a compound that generates an acid when exposed to actinic rays or radiation, and any of basic compounds of general formula (1) below.
    Type: Grant
    Filed: March 15, 2012
    Date of Patent: February 4, 2014
    Assignee: FUJIFILM Corporation
    Inventors: Kana Fujii, Tomotaka Tsuchimura, Toru Fujimori, Hidenori Takahashi, Takayuki Ito
  • Patent number: 8637220
    Abstract: An actinic ray-sensitive or radiation-sensitive resin composition comprising (A) a guanidine compound having a logP value of 1.2 or more, and (B) a compound capable of generating an acid upon irradiation with an actinic ray or radiation.
    Type: Grant
    Filed: June 29, 2011
    Date of Patent: January 28, 2014
    Assignee: FUJIFILM Corporation
    Inventors: Tomotaka Tsuchimura, Hideaki Tsubaki, Toshiya Takahashi
  • Patent number: 8632939
    Abstract: A polymer comprising recurring units having a fluorinated carboxylic acid onium salt structure on a side chain is used to formulate a chemically amplified positive resist composition. When the composition is processed by lithography to form a positive pattern, the diffusion of acid in the resist film is uniform and slow, and the pattern is improved in LER.
    Type: Grant
    Filed: February 25, 2011
    Date of Patent: January 21, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Keiichi Masunaga, Satoshi Watanabe, Jun Hatakeyama, Youichi Ohsawa, Daisuke Domon
  • Patent number: 8632960
    Abstract: A method of forming a resist pattern, including: forming a resist film on a substrate using a resist composition containing a base component (A) which exhibits decreased solubility in an organic solvent under action of an acid and an acid-generator component (B) which generates an acid upon exposure, conducting exposure of the resist film, and patterning the resist film by a negative tone development using a developing solution containing an organic solvent, wherein the base component (A) includes a resin component (A1) containing a structural unit (a0) derived from an acrylate ester containing an acid decomposable group which generates an alcoholic hydroxy group by the action of acid to thereby exhibit increased hydrophilicity.
    Type: Grant
    Filed: February 16, 2011
    Date of Patent: January 21, 2014
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Tomoyuki Hirano, Takahiro Dazai, Daiju Shiono, Sho Abe