Halogen Compound Containing Patents (Class 430/925)
  • Patent number: 8691490
    Abstract: There is disclosed a sulfonium salt represented by the following general formula (1). In the formula, X and Y each represents a group having a polymerizable functional group; Z represents a divalent hydrocarbon group having 1 to 33 carbon atoms optionally containing a hetero atom; R1 represents a divalent hydrocarbon group having 1 to 36 carbon atoms optionally containing a hetero atom; and R2 and R3 each represents a monovalent hydrocarbon group having 1 to 30 carbon atoms optionally containing a hetero atom or R2 and R3 may be bonded with each other to form a ring together with a sulfur atom in the formula. There can be provided a sulfonium salt usable as a resist composition providing high resolution and excellent in LER in photolithography using a high energy beam such as an ArF excimer laser, an EUV light and an electron beam as a light source, a polymer obtained from the sulfonium salt, a resist composition containing the polymer and a patterning process using the resist composition.
    Type: Grant
    Filed: January 25, 2011
    Date of Patent: April 8, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Masaki Ohashi, Satoshi Watanabe, Youichi Ohsawa, Keiichi Masunaga, Takeshi Kinsho
  • 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: 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: 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: 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: 8628908
    Abstract: A chemically amplified resist composition is provided comprising (A) a specific tertiary amine compound, (B) a specific acid generator, (C) a base resin having an acidic functional group protected with an acid labile group, which is substantially insoluble in alkaline developer and turns soluble in alkaline developer upon deprotection of the acid labile group, and (D) an organic solvent. The resist composition has a high resolution, improved defect control in the immersion lithography, and good shelf stability.
    Type: Grant
    Filed: February 28, 2012
    Date of Patent: January 14, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takeru Watanabe, Tomohiro Kobayashi, Masayoshi Sagehashi, Takeshi Nagata, Youichi Ohsawa, Ryosuke Taniguchi
  • Patent number: 8628909
    Abstract: The present invention relates to a fluorine-free photoacid generator (PAG) and a photoresist composition containing the same. The PAG is characterized by the presence of an onium cationic component and a fluorine-free fused ring heteroaromatic sulfonate anionic component containing one or more electron withdrawing substituents. The onium cationic component of the PAG is preferably a sulfonium or an iodonium cation. The photoresist composition further contains an acid sensitive imaging polymer. The photoresist composition is especially useful for forming material patterns on a semiconductor substrate using 193 nm (ArF) lithography.
    Type: Grant
    Filed: September 14, 2012
    Date of Patent: January 14, 2014
    Assignee: International Business Machines Corporation
    Inventors: Sen Liu, Pushkara R. Varanasi
  • Patent number: 8628910
    Abstract: The present invention relates to a fluorine-free photoacid generator (PAG) and a photoresist composition containing the same. The PAG is characterized by the presence of an onium cationic component and a fluorine-free fused ring heteroaromatic sulfonate anionic component containing one or more electron withdrawing substituents. The onium cationic component of the PAG is preferably a sulfonium or an iodonium cation. The photoresist composition further contains an acid sensitive imaging polymer. The photoresist composition is especially useful for forming material patterns on a semiconductor substrate using 193 nm (ArF) lithography.
    Type: Grant
    Filed: September 14, 2012
    Date of Patent: January 14, 2014
    Assignee: International Business Machines Corporation
    Inventors: Sen Liu, Pushkara R. Varanasi
  • Patent number: 8623584
    Abstract: The present invention relates to a fluorine-free photoacid generator (PAG) and a photoresist composition containing the same. The PAG is characterized by the presence of an onium cationic component and a fluorine-free fused ring heteroaromatic sulfonate anionic component containing one or more electron withdrawing substituents. The onium cationic component of the PAG is preferably a sulfonium or an iodonium cation. The photoresist composition further contains an acid sensitive imaging polymer. The photoresist composition is especially useful for forming material patterns on a semiconductor substrate using 193 nm (ArF) lithography.
    Type: Grant
    Filed: September 14, 2012
    Date of Patent: January 7, 2014
    Assignee: International Business Machines Corporation
    Inventors: Sen Liu, Pushkara R. Varanasi
  • Patent number: 8617790
    Abstract: A photoresist composition comprising (A) a resin which has an acid-labile group-containing structural unit and a lactone ring-containing structural unit, and (B) a salt represented by formula (I): wherein Q1 and Q2 each independently represent a fluorine atom or a C1-C6 perfluoroalkyl group, n represents 0 or 1, L1 represents a single bond or a C1-C10 alkanediyl group in which a methylene group may be replaced by an oxygen atom or a carbonyl group, provided that L1 is not a single bond when n is 0, R1 represents a hydroxy group or a hydroxy group protected by a protecting group, and Z+ represents an organic cation.
    Type: Grant
    Filed: April 17, 2012
    Date of Patent: December 31, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Yukako Anryu, Shingo Fujita
  • Patent number: 8617786
    Abstract: The present invention relates to compositions comprising poly-oxycarbosilane and methods for using the compositions in step and flash imprint lithography. The imprinting compositions comprise a poly-oxycarbosilane polymer, a silanol, a reaction initiator and optionally a pore generator.
    Type: Grant
    Filed: February 11, 2011
    Date of Patent: December 31, 2013
    Assignee: International Business Machines Corporation
    Inventors: Richard Anthony Dipietro, Geraud Jean-Michel Dubois, Robert Dennis Miller, Ratnam Sooriyakumaran
  • Patent number: 8614047
    Abstract: Provided are novel symmetrical and asymmetrical bifunctional photodecomposable bases (PDBs) with dicarboxylate anion groups that show increased imaging performance. Also provided are photoresist compositions prepared with the bifunctional dicarboxylated PDBs and lithography methods that use the photoresist compositions of the present invention.
    Type: Grant
    Filed: August 26, 2011
    Date of Patent: December 24, 2013
    Assignees: International Business Machines Corporation, JSR Corporation
    Inventors: Ramakrishnan Ayothi, William D. Hinsberg, Sally A. Swanson, Gregory M. Wallraff
  • Patent number: 8609891
    Abstract: New photoacid generator compounds are provided that comprise a nitrogen-base functional component of the structure —C(?O)N<. Photoresist compositions also are provided that comprise one or more PAGs of the invention.
    Type: Grant
    Filed: April 27, 2011
    Date of Patent: December 17, 2013
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: Young Cheol Bae, Thomas Cardolaccia, Yi Liu
  • Patent number: 8609889
    Abstract: The photoacid generator produces a sulfonic acid which has a bulky cyclic structure in the sulfonate moiety and a straight-chain hydrocarbon group and thus shows a controlled acid diffusion behavior and an adequate mobility. The PAG is fully compatible with a resin to form a resist composition which performs well during the device fabrication process and solves the problems of resolution, LWR, and exposure latitude.
    Type: Grant
    Filed: July 1, 2010
    Date of Patent: December 17, 2013
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Masaki Ohashi, Youichi Ohsawa, Takeshi Kinsho, Takeru Watanabe
  • Patent number: 8597869
    Abstract: A sulfonium salt of a naphthyltetrahydrothiophenium cation having a fluoroalkoxy chain with a specific anion is provided. The sulfonium salt is used as a photoacid generator to form a resist composition which when processed by immersion lithography, offers advantages of restrained dissolution in the immersion water and less pattern dependence or dark/bright bias.
    Type: Grant
    Filed: September 23, 2011
    Date of Patent: December 3, 2013
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Masayoshi Sagehashi, Youichi Ohsawa, Koji Hasegawa, Takeshi Kinsho, Tomohiro Kobayashi
  • Patent number: 8586281
    Abstract: A positive resist composition including: a base component; and a sensitizer which a polymeric compound having a core portion that includes a hydrocarbon group or a heterocycle of two or more valences and at least one arm portion bonded to the core portion and represented by formula (1), and a polymeric compound having a core portion including a polymer having a molecular weight of 500 to 20,000 and at least one arm portion bonded to the core portion and represented by formula (1); and either the base component includes a resin component that generates acid upon exposure and exhibits increased solubility in an alkali developing solution under action of acid, or the positive resist composition further contains an acid generator component including a compound that generates acid upon exposure: —(X)—Y??(1) in which X represents a divalent linking group having an acid dissociable group; and Y represents a polymer chain.
    Type: Grant
    Filed: June 8, 2011
    Date of Patent: November 19, 2013
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Jun Iwashita, Masahito Yahagi, Kenri Konno, Isamu Takagi
  • Patent number: 8580486
    Abstract: There is provided an acid having a fluorine-containing carbanion structure or a salt having a fluorine-containing carbanion structure, which is represented by the following general formula (1). By using a photoacid generator for chemically amplified resist materials that generates this acid, it is possible to provide a photoacid generator which has a high sensitivity to the ArF excimer laser light or the like, of which acid (photo generated acid) to be generated has a sufficiently high acidity, and which has a high dissolution in resist solvent and a superior compatibility with resin, and a resist material containing such a photoacid generator.
    Type: Grant
    Filed: March 10, 2009
    Date of Patent: November 12, 2013
    Assignee: Central Glass Company, Limited
    Inventors: Masashi Nagamori, Satoru Narizuka, Susumu Inoue, Takashi Kume
  • Patent number: 8574811
    Abstract: A resist composition contains; a resin having a structural unit derived from a compound represented by the formula (a); and an acid generator. wherein R1 represents a hydrogen atom or a methyl group; R2 represents an optionally substituted C1 to C18 aliphatic hydrocarbon group; A1 represents an optionally substituted C1 to C6 alkanediyl group or a group represented by the formula (a-g1); wherein s represents 0 or 1; A10 and A12 independently represent an optionally substituted C1 to C5 aliphatic hydrocarbon group; A11 represents a single bond or an optionally substituted C1 to C5 aliphatic hydrocarbon group; X10 and X11 independently represents an oxygen atom, a carbonyl group, a carbonyloxy group or an oxycarbonyl group; provided that a total number of the carbon atom of A10, A11, A12, X10 and X11 is 6 or less.
    Type: Grant
    Filed: August 30, 2011
    Date of Patent: November 5, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tatsuro Masuyama, Satoshi Yamamoto, Koji Ichikawa
  • Patent number: 8574817
    Abstract: A positive resist composition comprising a polymer having carboxyl groups substituted with an acid labile group having formula (1), (2) or (3) exhibits a high contrast of alkaline dissolution rate before and after exposure, a high resolution, a reduced acid diffusion rate, and forms a pattern with good profile, minimal edge roughness, and etch resistance. In formula (1), R1, R2, R5, R6, R8, and R9 are alkyl, aryl, or alkenyl, R3, R4, R7, R10, and R11 are hydrogen, alkyl, alkoxy, acyloxy, halogen, cyano, nitro, hydroxyl or trifluoromethyl, M is methylene or ethylene, R is a single bond or linking group.
    Type: Grant
    Filed: September 13, 2012
    Date of Patent: November 5, 2013
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Koji Hasegawa
  • Patent number: 8557500
    Abstract: The present invention provides a salt represented by the formula (I): wherein Q1 and Q2 independently each represent a fluorine atom or a C1-C6 perfluoroalkyl group, L1 represents a C1-C17 divalent saturated hydrocarbon group in which one or more —CH2— can be replaced by —O— or —CO—, L2 represents a single bond or a C1-C6 alkanediyl group in which one or more —CH2— can be replaced by —O— or —CO—, Y represents a C3-C18 alicyclic hydrocarbon group which can have one or more substituents, and one or more —CH2— in the alicyclic hydrocarbon group can be replaced by —O—, —CO— or —SO2—, and Z+ represents an organic counter ion.
    Type: Grant
    Filed: February 28, 2012
    Date of Patent: October 15, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Hiromu Sakamoto, Takahiro Yasue
  • Patent number: 8557498
    Abstract: A photosensitive resin composition is used that comprises a photosensitive silicone having a styryl group as a photosensitive group, and a photopolymerization initiator having a specific structure. As a result, a photosensitive resin composition capable of being cured in air by photopolymerization that is preferable for use as a buffer coat material or rewiring layer of an LSI chip, a method for forming a cured relief pattern using this photosensitive resin composition, and a semiconductor device comprising the cured relief pattern are provided.
    Type: Grant
    Filed: March 25, 2008
    Date of Patent: October 15, 2013
    Assignee: Asahi Kasei E-Materials Corporation
    Inventor: Tomohiro Yorisue
  • Patent number: 8546059
    Abstract: The present invention provides a photoresist composition comprising a resin, an acid generator and a compound represented by the formula (C1): wherein Rc1 represents an aromatic group which can have one or more substituents, Rc2 and Rc3 independently each represent a hydrogen atom, an aliphatic hydrocarbon group which can have one or more substituents or an aromatic group which can have one or more substituents, Rc4 and Rc6 independently each represent a hydrogen atom or an aliphatic hydrocarbon group which can have one or more substituents, or Rc4 and Rc6 are bonded each other to form an alkanediyl group, Rc5 represents an aliphatic hydrocarbon group which can have one or more substituents or an amino group which can have one or two substituents, Rc7 represents a hydrogen atom or an aliphatic hydrocarbon group which can have one or more substituents, or Rc5 and Rc7 are bonded each other to form an alkanediyl group.
    Type: Grant
    Filed: November 24, 2010
    Date of Patent: October 1, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Takayuki Miyagawa, Mitsuhiro Hata
  • Patent number: 8541157
    Abstract: A resist composition including a base component (A) which exhibits changed solubility in an alkali developing solution under the action of acid and an acid-generator component (B) which generates acid upon exposure, wherein the acid-generator component (B) includes an acid generator (B1) composed of a compound having a base dissociable group within a cation moiety.
    Type: Grant
    Filed: September 25, 2009
    Date of Patent: September 24, 2013
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Akiya Kawaue, Yoshiyuki Utsumi, Sho Abe
  • Patent number: 8541161
    Abstract: Provided are an actinic ray-sensitive or radiation-sensitive resin composition; a resist film using the composition; and a pattern forming method. The actinic ray-sensitive or radiation-sensitive resin composition includes (A) a resin capable of increasing the solubility in an alkali developer by the action of an acid, the resin containing a repeating unit represented by formula (I), a repeating unit represented by formula (II) and a repeating unit represented by formula (III), and (B) a compound capable of generating a fluorine atom-containing acid upon irradiation with an actinic ray or radiation: wherein each of R1 and R11 independently represents a hydrogen atom or an alkyl group which may have a substituent, and R12 represents a phenyl group which may have a substituent.
    Type: Grant
    Filed: March 23, 2010
    Date of Patent: September 24, 2013
    Assignee: FUJIFILM Corporation
    Inventors: Kana Fujii, Shuji Hirano, Shinki Yamada, Toru Fujimori
  • Patent number: 8535869
    Abstract: A sulfonium salt of a naphthylsulfonium cation having a hydrophilic phenolic hydroxyl group or ethylene glycol chain with a specific anion is provided. The sulfonium salt is used as a photoacid generator to form a resist composition which when processed by immersion lithography, offers advantages of restrained dissolution in the immersion water and less pattern dependence or dark-bright difference.
    Type: Grant
    Filed: August 22, 2011
    Date of Patent: September 17, 2013
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Masayoshi Sagehashi, Tomohiro Kobayashi
  • Patent number: 8530135
    Abstract: The present invention provides a photoresist composition comprising a resin 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, an acid generator and a compound represented by the formula (I): wherein Z1 represents a C7-C20 alkylene group, a C3-C20 divalent saturated cyclic group or a divalent group formed by combining at least one C1-C6 alkylene group with at least one C3-C20 divalent saturated cyclic group.
    Type: Grant
    Filed: September 22, 2010
    Date of Patent: September 10, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Satoshi Yamaguchi, Soon Shin Kim, Isao Yoshida, Koji Ichikawa
  • Patent number: 8524440
    Abstract: The present invention provides a photoresist composition comprising a resin which comprises a structural unit represented by the formula (I): wherein Q1 and Q2 independently represent a fluorine atom etc., U represents a C1-C20 divalent hydrocarbon group etc., X1 represents —O—CO— etc., and A+ represents an organic counter ion, and a compound represented by the formula (D?): wherein R51, R52, R53 and R54 independently represent a C1-C20 alkyl group etc., and A11 represents a C1-C36 saturated cyclic hydrocarbon group which may have one or more substituents and which may contain one or more heteroatoms.
    Type: Grant
    Filed: January 3, 2011
    Date of Patent: September 3, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yuko Yamashita, Nobuo Ando
  • Patent number: 8507180
    Abstract: Disclosed are a chemically amplified positive-type photoresist composition for a thick film, a chemically amplified dry film for a thick film, and a method for producing a thick film resist pattern, all of which are capable of obtaining a satisfactory resist pattern with high sensitivity even on a substrate having a portion formed of copper on an upper surface thereof. The chemically amplified positive-type photoresist composition for a thick film comprises component (A) which includes at least one compound capable of producing an acid upon irradiation with an actinic ray or radiation, and component (B) which includes at least one resin whose alkali solubility increases by the action of an acid, in which the component (A) includes an onium fluorinated alkyl fluorophosphate having a specific structure.
    Type: Grant
    Filed: October 18, 2007
    Date of Patent: August 13, 2013
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Yasushi Washio, Kazuhide Uno, Koichi Misumi, Takahiro Senzaki, Koji Saito, Nobuko Ohgake
  • Patent number: 8501384
    Abstract: A positive resist composition comprising a polymer having a tetrahydrobenzocycloheptane-substituted secondary or tertiary carboxyl group ester as an acid labile group exhibits a high contrast of alkaline dissolution rate before and after exposure, a high resolution, a good pattern profile and minimal edge roughness after exposure, a significant effect of suppressing acid diffusion rate, and improved etching resistance.
    Type: Grant
    Filed: January 7, 2011
    Date of Patent: August 6, 2013
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Takeru Watanabe, Seiichiro Tachibana
  • Patent number: 8501382
    Abstract: There are disclosed sulfonic acid precursor compositions, as are methods of using these compositions in, for example, photolithography. Other embodiments are also disclosed.
    Type: Grant
    Filed: February 19, 2010
    Date of Patent: August 6, 2013
    Assignee: The Research Foundation of State Univ. of New York
    Inventor: Robert L. Brainard
  • Patent number: 8470513
    Abstract: A radiation-sensitive resin composition includes a polymer that includes at least one repeating unit (i) selected from a repeating unit shown by a formula (1), (2), and (3); and a repeating unit (ii) shown by a formula (4). R1 represents a hydrogen atom or a methyl group. Each R2 independently represents one of a linear or branched alkyl group having 1 to 12 carbon atoms, a linear or branched alkoxy group having 1 to 12 carbon atoms, and an alicyclic hydrocarbon group having 3 to 25 carbon atoms. p is an integer from 0 to 3, and q is an integer from 1 to 3, and p+q?5. A chemically-amplified positive-tone resist film that is sensitive to extreme ultraviolet rays (EUV) can be formed using the radiation-sensitive resin composition.
    Type: Grant
    Filed: September 23, 2011
    Date of Patent: June 25, 2013
    Assignee: JSR Corporation
    Inventors: Kota Nishino, Ken Maruyama, Daisuke Shimizu, Toshiyuki Kai
  • Patent number: 8460851
    Abstract: A salt represented by the formula (I): wherein Q1 and Q2 each independently represent a fluorine atom or a C1-C6 perfluoroalkyl group, L1 represents *—CO—O-La- or *—CH2—O-Lb-, * represents a binding position to —C(Q1)(Q2)-, La and Lb independently represent a C1-C15 divalent saturated hydrocarbon group in which one or more —CH2— can be replaced by —O— or —CO—, ring W1 represents a C2-C36 nitrogen-containing heterocyclic group in which one or more —CH2— can be replaced by —O—, and Z1? represents an organic counter ion.
    Type: Grant
    Filed: January 6, 2011
    Date of Patent: June 11, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Satoshi Yamaguchi, Koji Ichikawa
  • Patent number: 8450041
    Abstract: An actinic ray-sensitive or radiation-sensitive resin composition includes (A) a compound capable of generating a specific acid having a norbornyl structure upon irradiation with an actinic ray or radiation, and (B) a resin capable of increasing the dissolution rate of the resin (B) in an alkali developer by an action of an acid, the resin (B) containing a specific repeating unit having a lactone structure on the resin side chain through a linking group, and a pattern forming method uses the composition.
    Type: Grant
    Filed: January 15, 2010
    Date of Patent: May 28, 2013
    Assignee: FUJIFILM Corporation
    Inventor: Shuhei Yamaguchi
  • Patent number: 8440384
    Abstract: A compound has a partial structure shown by a following formula (1), wherein R1 represents a hydrogen atom or a substituted or unsubstituted hydrocarbon group having 1 to 8 carbon atoms, R2 represents a substituted or unsubstituted hydrocarbon group having 1 to 8 carbon atoms, Rf represents a fluorine atom or a perfluoroalkyl group having 1 to 4 carbon atoms, L represents an integer from 0 to 4, n represents an integer from 0 to 10, and m represents an integer from 1 to 4.
    Type: Grant
    Filed: April 14, 2010
    Date of Patent: May 14, 2013
    Assignee: JSR Corporation
    Inventors: Takuma Ebata, Tomoki Nagai
  • Patent number: 8435717
    Abstract: A sulfonic acid onium salt represented by the following formula (1) can be used as a superior radiosensitive acid generator for resist compositions. It is possible to form a good pattern by using a resist composition containing this sulfonic acid onium salt. In formula (1), R1 represents a monovalent organic group, and Q+ represents a sulfonium cation or iodonium cation.
    Type: Grant
    Filed: February 14, 2008
    Date of Patent: May 7, 2013
    Assignee: Central Glass Company, Limited
    Inventors: Yuji Hagiwara, Jonathan Joachim Jodry, Satoru Narizuka, Kazuhiko Maeda
  • Patent number: 8431324
    Abstract: A radiation-sensitive resin composition includes a resin, a radiation-sensitive acid generator, an acid diffusion controller, and a mixed solvent. The radiation-sensitive acid generator includes a compound (I) shown by a following general formula (I). The mixed solvent includes about 50 mass % to about 90 mass % of propylene glycol monomethyl ether acetate, wherein M+ represents a sulfonium cation or an iodonium cation, R represents a hydrogen atom or a hydrocarbon group having 1 to 8 carbon atoms, Rf represents a fluorine atom or a perfluoroalkyl group having 1 to 4 carbon atoms, n represents an integer from 1 to 10, and m represents an integer from 1 to 4.
    Type: Grant
    Filed: May 7, 2010
    Date of Patent: April 30, 2013
    Assignee: JSR Corporation
    Inventors: Tsutomu Shimokawa, Takuma Ebata
  • Patent number: 8426113
    Abstract: The present invention provides chemically amplified silsesquioxane polymers for preparing masks using e-beam lithography. The silsesquioxane polymers have reactive sidechains that in the presence of an acid undergo acid catalyzed rearrangement to generate reactive functionalities that crosslink to form Si—O—Si bonds. The reactive side-chains comprise ?- and ?-substituted alkyl groups bound to the silicon of the silsesquioxane polymer. The substituent of the ?- and ?-substituted alkyl group is an electron withdrawing group. Resists generated with the chemically amplified silsesquioxane polymers of the present invention and imaged with e-beams have resolution of ?60 nm line/space.
    Type: Grant
    Filed: August 13, 2010
    Date of Patent: April 23, 2013
    Assignee: International Business Machines Corporation
    Inventors: Luisa Dominica Bozano, Blake W. Davis, Alshakim Nelson, Jitendra Singh Rathore, Linda Karin Sundberg
  • Patent number: 8426106
    Abstract: A Photoresist composition comprising a polymer comprising a structural unit derived from a compound represented by the formula (I): wherein R1 represents a hydrogen atom or a methyl group, R2 represents a C6-C12 aromatic hydrocarbon group which can have one or more substituents, R3 represents a cyano group or a C1-C12 hydrocarbon group which can have one or more substituents and which can contain one or more heteroatoms, A1 represents a single bond, —(CH2)g—CO—O—* or —(CH2)h—O—CO—(CH2)i—CO—O—* wherein g, h and i each independently represent an integer of ?1 to 6 and * represents a binding position to the nitrogen atom, a resin 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, and an acid generator.
    Type: Grant
    Filed: October 12, 2010
    Date of Patent: April 23, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tatsuro Masuyama, Kazuhiko Hashimoto, Junji Shigematsu
  • Patent number: 8420299
    Abstract: It is therefore an object of the present invention to provide a forming method for a resist pattern to reduce a resist residue in forming the resist pattern on a step whose gradient angle is equal to 90 degrees or more. A forming method for a resist pattern to reduce a resist residue on a step is provided, the method comprising: forming resist film with coating resist containing photo-acid-generator on a step formed on a substrate, where gradient angle of the step is equal to 90 degrees or more, exposing said resist film and generating acid from said photo-acid-generator.
    Type: Grant
    Filed: August 6, 2008
    Date of Patent: April 16, 2013
    Assignee: TDK Corporation
    Inventors: Hisayoshi Watanabe, Susumu Aoki
  • Patent number: 8415085
    Abstract: 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) including a compound represented by (b1-1), a compound represented by (b1-1?) and/or a compound represented by (b1-1?) (R1?-R3? represents an aryl group or an alkyl group, provided that at least one of R1?-R3? represents a substituted aryl group being substituted with a group represented by (b1-1-0), and two of R1?-R3? may be mutually bonded to form a ring with the sulfur atom; X represents a C3-C30 hydrocarbon group; Q1 represents a carbonyl group-containing divalent linking group; X10 represents a C1-C30 hydrocarbon group; Q3 represents a single bond or a divalent linking group; Y10 represents —C(?O)— or —SO2—; Y11 represents a C1-C10 alkyl group or a fluorinated alkyl group: Q2 represents a single bond or an alkylene group; and W represents a C2-C10 alkylene group).
    Type: Grant
    Filed: May 23, 2012
    Date of Patent: April 9, 2013
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hideo Hada, Yoshiyuki Utsumi, Takehiro Seshimo, Akiya Kawaue
  • Patent number: 8415081
    Abstract: The present invention discloses a photosensitive resin composition which comprises (A) a compound having a molecule with at least one thiirane ring and a total number of a thiirane ring and/or an epoxy ring of at least 2 in the molecule, and (B) a photo acid generator, said composition having a refractive index of at least 1.6, and a method of obtaining a high refractive index periodical structure which comprises subjecting the photosensitive resin composition to photolithography.
    Type: Grant
    Filed: June 17, 2004
    Date of Patent: April 9, 2013
    Assignees: Cornell Research Foundation, Inc., Hitachi Chemical Co., Ltd.
    Inventors: Christopher K. Ober, Yasuharu Murakami
  • Patent number: 8367299
    Abstract: 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, wherein said acid-generator component (B) comprises an acid generator (B1) including a compound represented by general formula (b1-11) shown below: wherein R7? to R9? each independently represent 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 having a group represented by general formula (I) shown below as a substituent; X? represents an anion; and Rf represents a fluorinated alkyl group.
    Type: Grant
    Filed: September 15, 2011
    Date of Patent: February 5, 2013
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Akiya Kawaue, Yoshiyuki Utsumi, Takehiro Seshimo, Tsuyoshi Nakamura, Naoto Motoike, Hiroaki Shimizu, Kensuke Matsuzawa, Hideo Hada
  • Patent number: 8349533
    Abstract: A resist lower-layer composition configured to be used by a multi-layer resist method used in lithography to form a layer lower than a photoresist layer acting as a resist upper layer film. The resist lower-layer composition is insoluble or poorly-soluble in an alkaline developer after formation of the lower layer, and the resist lower-layer composition comprises, at least, a thermal acid generator for generating an acid by heating at a temperature of 100° C. or higher.
    Type: Grant
    Filed: October 20, 2009
    Date of Patent: January 8, 2013
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Jun Hatakeyama, Takeru Watanabe, Takeshi Kinsho
  • Patent number: 8349535
    Abstract: According to one embodiment, an actinic ray-sensitive or radiation-sensitive resin composition includes (A) a resin containing the repeating units of formulae (I), (II) and (III) that when acted on by an acid, becomes soluble in an alkali developer, and (B) a compound that when irradiated with actinic rays or radiation, generates a fluorine-containing acid, wherein each of R1 independently represents a hydrogen atom or an optionally substituted methyl group, R2 represents a halogen atom, an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted aryl group or an optionally substituted aralkyl group, and n is an integer of 0 to 5, provided that when n is 2 or greater, multiple R2s may be identical to or different from each other.
    Type: Grant
    Filed: September 30, 2010
    Date of Patent: January 8, 2013
    Assignee: FUJIFILM Corporation
    Inventors: Kana Fujii, Takamitsu Tomiga, Toru Tsuchihashi, Kazuyoshi Mizutani, Jiro Yokoyama, Shinichi Sugiyama, Shuji Hirano, Toru Fujimori
  • Patent number: 8338074
    Abstract: It is intended to provide the following resin composition for stereolithography which is superior in storage stability and aging stability during operation, shows no increase in viscosity upon prolonged storage, has a high light-curing sensitivity and, therefore, makes it possible to produce, upon photo irradiation, an object by stereolithography, which is superior in dimensional accuracy, fabricating accuracy, water resistance, moisture resistance and mechanical properties at a high fabricating speed and a high productivity.
    Type: Grant
    Filed: June 24, 2004
    Date of Patent: December 25, 2012
    Assignees: CMET Inc., San-Apro Ltd.
    Inventors: Takashi Ito, Tsuneo Hagiwara, Hideki Kimura, Masashi Date, Jiro Yamamoto
  • Patent number: 8338077
    Abstract: This invention relates to new photoacid generator compounds and photoresist compositions that comprise such compounds. In particular, the invention relates to photoacid generator compounds that comprise a multi cyclic lactone moiety.
    Type: Grant
    Filed: June 22, 2010
    Date of Patent: December 25, 2012
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: Mingqi Li, Cheng-Bai Xu, Emad Aqad, Cong Liu
  • Patent number: 8334088
    Abstract: Linear or branched functionalized polycarbosilanes having an absorbance less than 3.0 ?m?1 at 193 nm and a relatively high refractive index are provided. The functionalized polycarbosilanes contain at least one pendant group that is acid labile or aqueous base soluble. Also disclosed are photoresists formulations containing the functionalized polycarbosilanes that are suitable for use in lithography, e.g., immersion lithography.
    Type: Grant
    Filed: November 3, 2010
    Date of Patent: December 18, 2012
    Assignee: International Business Machines Corporation
    Inventors: Robert D. Allen, Matthew E. Colburn, Daniel P. Sanders, Ratnam Sooriyakumaran, Hoa D. Truong
  • Patent number: 8298746
    Abstract: The present invention provides a chemically amplified resist composition comprising: a resin (A) 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 and which comprises a structural unit having an acid-labile group in a side chain and a structural unit represented by the formula (I): wherein R1 represents a hydrogen atom or a methyl group, ring X1 represents an unsubstituted or substituted C3-C30 cyclic hydrocarbon group having —COO— and k represents an integer of 1 to 4, a resin (B) which comprises a structural unit represented by the formula (II): wherein R2 represents a hydrogen atom, a methyl group or a trifluoromethyl group, and an acid generator.
    Type: Grant
    Filed: June 24, 2009
    Date of Patent: October 30, 2012
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Junji Shigematsu, Kunishige Edamatsu, Takayuki Miyagawa, Akira Kamabuchi
  • Patent number: 8288078
    Abstract: A photosensitive resin composition is provided that is highly safe, provides a coating film having superior uniformity, can improve the curing density of the cured resin pattern, and is capable of forming a micro resist pattern having a large film thickness and a high aspect ratio with high sensitivity and high resolving ability. According to a photosensitive resin composition including, in addition to an onium fluorinated alkyl fluorophosphate based cation polymerization initiator having a specific structure, a specified solvent or a specified sensitizing agent as essential components, a coating film having superior uniformity, can improve the curing density of the cured resin pattern, and also is capable of forming a micro resist pattern having a large film thickness and a high aspect ratio with high sensitivity and high resolving ability.
    Type: Grant
    Filed: January 11, 2008
    Date of Patent: October 16, 2012
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Takahiro Senzaki, Koichi Misumi, Atsushi Yamanouchi, Koji Saito
  • Patent number: 8247160
    Abstract: A resist composition including a base component that exhibits changed solubility in an alkali developing solution under the action of acid, and an acid generator consisting of a compound represented by general formula (b1). In formula (b1), Y1 represents a fluorinated alkylene group of 1 to 4 carbon atoms, X represents an aliphatic cyclic group of 3 to 30 carbon atoms, R11? to R13? each represents an aryl group or alkyl group, provided that at least one of R11? to R13? is an aryl group having a substituent represented by general formula (b1-0), and two alkyl groups among R11? to R13? may be bonded to each other to form a ring with the sulfur atom in the formula. In formula (b1-0), R52 represents a chain-like or cyclic hydrocarbon group, and f and g each represents 0 or 1.
    Type: Grant
    Filed: July 13, 2009
    Date of Patent: August 21, 2012
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Yoshiyuki Utsumi, Keita Ishiduka, Kensuke Matsuzawa, Akiya Kawaue, Hiroaki Shimizu, Tsuyoshi Nakamura