Sulfur In Heterocyclic Ring Patents (Class 430/922)
  • Patent number: 8283106
    Abstract: Disclosed is a fluorinated sulfonic acid salt or fluorinated sulfonic acid group-containing compound having a structure represented by the following general formula (A). In the formula, n indicates an integer of 1 to 10; R indicates a substituted or unsubstituted C1-C20 linear, branched or cyclic alkyl group, a substituted or unsubstituted C1-C20 linear, branched or cyclic alkenyl group, a substituted or unsubstituted C6-C15 aryl group, or a C4-C15 heteroaryl group; and a indicates 1 or 0. A photoacid generator containing the above fluorinated sulfonic acid salt or fluorinated sulfonic acid group-containing compound shows high sensitivity to an ArF excimer laser or the like, presents no concerns about human body accumulation, can generate an acid (photoacid) of sufficiently high acidity, and exhibits high solubility in a resist solvent and good compatibility with a resist resin.
    Type: Grant
    Filed: October 31, 2008
    Date of Patent: October 9, 2012
    Assignee: Central Glass Company, Limited
    Inventors: Kazuhiko Maeda, Yoshimi Isono, Satoru Narizuka
  • Patent number: 8278030
    Abstract: An object of the present invention is to provide a sulfonium salt that has sufficient photosensitivity by active energy rays, such as visible light, ultraviolet rays, electron beams, and X-rays. The present invention is a sulfonium salt represented by formula (1). It is noted that R1 is a group represented by formula (2); R2 and R3 each represent an aryl group having 6 to 30 carbon atoms, a heterocyclic hydrocarbon group having 4 to 30 carbon atoms, an alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, or an alkynyl group having 2 to 30 carbon atoms; X? represents a monovalent polyatomic anion; R4 to R6 each represent an alkyl group, or the like; k represents an integer of 0 to 4; m represents an integer of 0 to 3; n represents an integer of 0 to 4; and A represents a group represented by —S—, —O—, —SO—, —SO2—, or —CO—.
    Type: Grant
    Filed: April 27, 2009
    Date of Patent: October 2, 2012
    Assignee: San-Apro Limited
    Inventors: Issei Suzuki, Hideki Kimura
  • Patent number: 8278023
    Abstract: A salt represented by the formula (I-BB): wherein Q1 and Q2 each independently represent a fluorine atom etc., X1 represents a single bond etc., Y1 represents a C1-C36 aliphatic hydrocarbon group etc., A1 and A2 independently each represents a C1-C20 aliphatic hydrocarbon group etc., Ar1 represents a (m4+1)-valent C6-C20 aromatic hydrocarbon group which can have one or more substituents, B1 represents a single bond etc., B2 represents a C4-C36 alicyclic hydrocarbon group which has one or more —OXa groups and which is not capable of being eliminated by the action of an acid etc., and Xa represents a hydrogen atom or a group capable of being eliminated by the action of an acid, m1 and m2 independently each represents an integer of 0 to 2, m3 represents an integer of 1 to 3, with the proviso that m1 plus m2 plus m3 equals 3, and m4 represents an integer of 1 to 3.
    Type: Grant
    Filed: May 25, 2010
    Date of Patent: October 2, 2012
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Masako Sugihara, Tatsuro Masuyama
  • Patent number: 8257905
    Abstract: A method of fabricating a thin film transistor substrate and a negative photoresist composition used therein are provided, which can reduce pattern inferiority. The method of fabricating a thin film transistor substrate includes forming a conductive film composed of a conductive material on a substrate, forming an etch pattern composed of a negative photoresist composition on the conductive film, and forming a conductive pattern by etching the conductive film using the etch pattern as an etching mask, wherein the negative photoresist composition includes 10-50 parts by weight of novolak resin including a hydroxyl group that is soluble in an alkali developing solution, 0.5-10 parts by weight of a first photo acid generator represented by the following formula (1), 0.
    Type: Grant
    Filed: January 11, 2010
    Date of Patent: September 4, 2012
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Yeong-Beom Lee, Hi-Kuk Lee, Byung-Uk Kim, Hyoc-Min Youn, Ki-Hyuk Koo
  • Patent number: 8252505
    Abstract: A resist composition including a base component (A) that exhibits changed solubility in an alkali developing solution under the action of acid, and an acid generator component (B) that generates acid upon exposure, wherein the acid generator component (B) includes an acid generator (B1) consisting of a compound represented by general formula (b1-2) shown below: [Chemical Formula 1] A+Z???(b1-2) wherein A+ represents an organic cation; and Z? represents an anionic cyclic group, wherein the cyclic group includes an ester linkage within the ring structure, two mutually different groups are bonded to the ring structure, one of these groups includes an ester linkage in which a carbon atom that constitutes part of the ester linkage is bonded directly to the ring structure, and the other group includes an anion moiety.
    Type: Grant
    Filed: February 16, 2009
    Date of Patent: August 28, 2012
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Akiya Kawaue, Keita Ishiduka, Kensuke Matsuzawa, Yoshiyuki Utsumi, Hiroaki Shimizu
  • 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
  • Patent number: 8206888
    Abstract: It is intended to provide a radiation-sensitive resin composition, which comprises a radiation-sensitive acid generator excellent in resolution performance, heat stability, and storage stability, suppresses fluctuations in line width and deterioration in pattern profile attributed to standing waves, and produces a resist pattern improved in nano edge roughness and LEF. The radiation-sensitive resin composition is characterized by (A) a radiation-sensitive acid generator comprising: a sulfonium salt compound typified by 2,4,6-trimethylphenyldiphenylsulfonium 2,4-difluorobenzenesulfonate, 2,4,6-trimethylphenyldiphenylsulfonium 4-trifluoromethylbenzenesulfonate, or the like; and a sulfonimide compound. It is preferred that the composition should further comprise (B) a resin typified by a 4-hydroxystyrene/4-t-butoxystyrene copolymer, a 4-hydroxystyrene/t-butyl (meth)acrylate, or the like.
    Type: Grant
    Filed: November 21, 2006
    Date of Patent: June 26, 2012
    Assignee: JSR Corporation
    Inventors: Yuuji Yada, Tomoki Nagai
  • Patent number: 8206891
    Abstract: A positive resist composition including: a base component (A) which includes a polymeric compound (A1) containing a structural unit (a0) represented by the general formula (a0-1) and a structural unit (a1) derived from an acrylate ester having an acid dissociable, dissolution inhibiting group; and an acid generator component (B) which includes an acid generator (B1) containing an anion moiety represented by the general formula (I): (in the formula (a0-1), R1 represents a hydrogen atom, a lower alkyl group of 1 to 5 carbon atoms or a halogenated lower alkyl group of 1 to 5 carbon atoms; R2 represents a bivalent linking group; and R3 represents a cyclic group containing —SO2— within the ring skeleton. In the formula (I), X represents a cyclic group of 3 to 30 carbon atoms, Q1 represents a bivalent linking group containing an oxygen atom; Y1 represents an alkylene group of 1 to 4 carbon atoms or a fluorinated alkylene group of 1 to 4 carbon atoms).
    Type: Grant
    Filed: October 5, 2009
    Date of Patent: June 26, 2012
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Takehiro Seshimo, Yoshiyuki Utsumi, Akiya Kawaue, Takahiro Dazai, Tomoyuki Hirano, Fumitake Kaneko, Kotaro Endo
  • Patent number: 8206886
    Abstract: A photosensitive composition comprises (A) a sulfonium or iodonium salt having an anion represented by one of formulae (I) and (II): wherein Y represents an alkylene group substituted with at least one fluorine atom, and R represents an alkyl group or a cycloalkyl group.
    Type: Grant
    Filed: January 25, 2005
    Date of Patent: June 26, 2012
    Assignee: FUJIFILM Corporation
    Inventor: Kunihiko Kodama
  • Patent number: 8173353
    Abstract: The present invention provides a sulfonium compound represented by the formula (I): wherein Q1 and Q2 each independently represent a fluorine atom or a C1-C6 perfluoroalkyl group, R1 represents a C5-C42 organic group having a ?-ketoester structure and A+ represents an organic counter ion, and a chemically amplified photoresist composition comprising the above-mentioned sulfonium compound 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: March 23, 2010
    Date of Patent: May 8, 2012
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tatsuro Masuyama, Junji Shigematsu, Hanwoo Park
  • Patent number: 8158326
    Abstract: A compound which generates a sulfonic acid having one or more —SO3H groups and one or more —SO2— bonds upon irradiation with an actinic ray or a radiation; a photosensitive composition containing the compound; and a method of pattern formation with the photosensitive composition.
    Type: Grant
    Filed: August 13, 2008
    Date of Patent: April 17, 2012
    Assignee: Fujifilm Corporation
    Inventors: Kunihiko Kodama, Kenji Wada, Kaoru Iwato
  • Patent number: 8124313
    Abstract: A compound represented by general formula (I); and a compound represented by general formula (b1-1). wherein Q1 represents a divalent linkage group or a single bond; Y1 represents an alkylene group which may have a substituent or a fluorinated alkylene group which may have a substituent; X represents a cyclic group of 3 to 30 carbon atoms which may have a substituent, and has an —SO2— bond in the structure thereof; M+ represents an alkali metal ion; and A+ represents an organic cation.
    Type: Grant
    Filed: January 22, 2010
    Date of Patent: February 28, 2012
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Takehiro Seshimo, Yoshiyuki Utsumi, Akiya Kawaue, Hideo Hada, Hiroaki Shimizu, Tsuyoshi Nakamura
  • Patent number: 8084183
    Abstract: A positive resist composition for electron beam, X-ray or EUV includes (A) a compound represented by the following formula (I), and (B) a resin capable of decomposing by the action of an acid to increase solubility in an alkali developing solution, which includes a repeating unit represented by the following formula (II) and a repeating unit represented by the following formula (III):
    Type: Grant
    Filed: August 1, 2008
    Date of Patent: December 27, 2011
    Assignee: Fujifilm Corporation
    Inventors: Katsuhiro Yamashita, Yasutomo Kawanishi
  • Patent number: 8048613
    Abstract: An alkali development-type solder resist includes (A) a carboxyl group-containing photosensitive resin obtained by reacting (a) a compound having two or more cyclic ether or thioether groups in the molecule with (b) an unsaturated monocarboxylic acid, reacting the product with (c) a polybasic acid anhydride, reacting the resulting resin with (d) a compound having a cyclic ether group and an ethylenic unsaturated group in the molecule, and reacting the product additionally with (c) a polybasic acid anhydride, (B) an oxime ester-based photopolymerization initiator containing a specific oxime ester group, (C) a compound having two or more ethylenic unsaturated groups in the molecule, and (D) a thermosetting component, wherein the dry film obtained by applying the composition has an absorbance of 0.3 to 1.2 per 25 ?m of the film thickness at a wavelength of 350 to 375 nm.
    Type: Grant
    Filed: October 13, 2008
    Date of Patent: November 1, 2011
    Assignee: Taiyo Ink Mfg. Co., Ltd.
    Inventors: Nobuhito Itoh, Yoko Shibasaki, Kenji Kato, Masao Arima
  • Patent number: 8039200
    Abstract: A photosensitive composition comprises (A) a sulfonium or iodonium salt having an anion represented by one of formulae (I) and (II): wherein Y represents an alkylene group substituted with at least one fluorine atom, and R represents an alkyl group or a cycloalkyl group.
    Type: Grant
    Filed: August 10, 2010
    Date of Patent: October 18, 2011
    Assignee: FUJIFILM Corporation
    Inventor: Kunihiko Kodama
  • Patent number: 8034533
    Abstract: Fluorine-free photoacid generators and photoresist compositions containing fluorine-free photoacid generators are enabled as alternatives to PFOS/PFAS photoacid generator-containing photoresists. The photoacid generators are characterized by the presence of a fluorine-free heteroaromatic sulfonate anionic component. The photoacid generators preferably contain an onium cationic component, more preferably a sulfonium cationic component. The photoresist compositions preferably contain an acid sensitive imaging polymer. The compositions are especially useful for forming material patterns using 193 nm (ArF) imaging radiation.
    Type: Grant
    Filed: January 16, 2008
    Date of Patent: October 11, 2011
    Assignee: International Business Machines Corporation
    Inventors: Sen Liu, Pushkara R. Varanasi
  • Patent number: 8021823
    Abstract: There is provided a positive resist composition, including a base component (A) which exhibits increased solubility in an alkali developing solution under action of an acid, and an acid generator component (B) which generates an acid upon exposure, wherein the base component (A) includes a polymeric compound (A1) containing a structural unit (a0) represented by the general formula (a0-1) shown below: (wherein, R1 represents a hydrogen atom, a lower alkyl group or a halogenated lower alkyl group; A represents a bivalent linking group; B represents a bivalent linking group; and R2 represents an acid dissociable, dissolution inhibiting group).
    Type: Grant
    Filed: February 18, 2009
    Date of Patent: September 20, 2011
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hiroaki Shimizu, Tsuyoshi Nakamura, Takahiro Dazai, Daiju Shiono, Tomoyuki Hirano
  • Patent number: 8021819
    Abstract: A photosensitive composition, which comprises a compound represented by formula (I): wherein R1 to R13 each independently represents a hydrogen atom or a substituent, and at least one of R1 to R13 is a substituent containing an alcoholic hydroxyl group; Z represents a single bond or a divalent linking group; and X? represents a counter anion; and a pattern-forming method using the photosensitive composition.
    Type: Grant
    Filed: February 7, 2007
    Date of Patent: September 20, 2011
    Assignee: FUJIFILM Corporation
    Inventor: Yasutomo Kawanishi
  • Patent number: 7989136
    Abstract: A photoresist composition comprises about 0.5 to about 20 parts by weight of a photo-acid generator, about 10 to about 70 parts by weight of a novolac resin containing a hydroxyl group, about 1 to about 40 parts by weight of a cross-linker that comprises an alkoxymethylmelamine compound, and about 10 to about 150 parts by weight of a solvent.
    Type: Grant
    Filed: March 31, 2008
    Date of Patent: August 2, 2011
    Assignees: Samsung Electronics Co., Ltd., Dongjin Semichem Co., Ltd.
    Inventors: Jeong-Min Park, Doo-Hee Jung, Hi-Kuk Lee, Hyoc-Min Yoon, Ki-Hyuk Koo
  • Patent number: 7935474
    Abstract: An acid-amplifier having an acetal group and a photoresist composition including the same, are disclosed. The acid-amplifier produces an acid (second acid) during a post-exposure-bake (PEB), which is induced by an acid (first acid) generated from a photo-acid generator (PAG) at the exposure process so that a line edge roughness (LER) of the photoresist pattern and photoresist energy sensitivity are improved. The acid-amplifier has a structure of following Formula 1. in Formula 1, R is C4˜C20 mono-cyclic or multi-cyclic saturated hydrocarbon, R1 is C1˜C10 linear hydrocarbon, C1˜C10 perfluoro compound or C5˜C20 aromatic compound, Ra and Rb are independently hydrogen atom or C1˜C4 saturated hydrocarbon and A is independently oxygen atom (O) or sulfur atom (S).
    Type: Grant
    Filed: July 17, 2008
    Date of Patent: May 3, 2011
    Assignee: Dongjin Semichem Co., Ltd.
    Inventors: Jung-Youl Lee, Min-Ja Yoo, Jeong-Sik Kim, Young-Bae Lim, Jae-Woo Lee, Jae-Hyun Kim
  • 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: 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: 7862980
    Abstract: The present invention provides a salt represented by the formula (I): wherein P1, P2, P3, Q1, Q2 and R are defined in the specification and the present invention further provides a chemically amplified resist composition comprising the salt represented by the above-mentioned formula (I).
    Type: Grant
    Filed: July 30, 2007
    Date of Patent: January 4, 2011
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yukako Harada, Isao Yoshida, Yoshiyuki Takata
  • Patent number: 7858287
    Abstract: A photosensitive resin realizes formation of a pattern having a good shape, without introducing poor compatibility between an acid generator and a photoresist primary-component polymer having an acid-dissociable group, and a photosensitive composition containing the photosensitive resin. The photosensitive resin includes a repeating unit represented by formula (1): (wherein R1 represents a C2-C9 linear or branched divalent hydrocarbon group; each of R2 to R5 represents a hydrogen atom or a C1-C3 linear or branched hydrocarbon group; each of R6 and R7 represents an organic group, wherein R6 and R7 may together form a divalent organic group; and X?represents an anion); at least one of a repeating unit represented by formula (2): (wherein R8 represents a C2-C9 linear or branched hydrocarbon group) and a repeating unit represented by formula (3): a repeating unit represented by formula (4): optionally, a repeating unit represented by formula (5).
    Type: Grant
    Filed: November 30, 2007
    Date of Patent: December 28, 2010
    Assignees: Hyogo Prefecture, Toyo Gosei Co., Ltd
    Inventors: Takeo Watanabe, Hiroo Kinoshita, Shinichi Yusa, Tomotaka Yamanaka, Masamichi Hayakawa, Yosuke Osawa, Satoshi Ogi, Yoshitaka Komuro
  • 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: 7851130
    Abstract: A photosensitive composition includes (A) a compound represented by the following formula (I): wherein R1 to R13 each independently represents a hydrogen atom or a substituent, Z represents a single bond or a divalent linking group, and X? represents an anion containing a proton acceptor functional group.
    Type: Grant
    Filed: September 19, 2007
    Date of Patent: December 14, 2010
    Assignee: FUJIFILM Corporation
    Inventors: Yasutomo Kawanishi, Kenji Wada
  • 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: 7807329
    Abstract: A photosensitive composition comprises (A) a specific compound, which is excellent in sensitivity, resolution, and defocus latitude (DOF), and a pattern-forming method using the photosensitive composition is provided.
    Type: Grant
    Filed: March 13, 2006
    Date of Patent: October 5, 2010
    Assignee: FUJIFILM Corporation
    Inventors: Kazuyoshi Mizutani, Yasutomo Kawanishi
  • 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: 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: 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: 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: 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: 7741015
    Abstract: A pattern is formed by applying a positive resist composition comprising a polymer comprising 7-oxanorbornane ring-bearing recurring units and acid labile group-bearing recurring units and an acid generator onto a substrate to form a resist film, heat treating and exposing the resist film to radiation, heat treating and developing the resist film with a developer, and causing the resist film to crosslink and cure with the aid of acid and/or heat. A second resist pattern is then formed in the space area of the first resist pattern. The double patterning process reduces the pitch between patterns to one half.
    Type: Grant
    Filed: February 12, 2008
    Date of Patent: June 22, 2010
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Takao Yoshihara, Takeshi Kinsho, Koji Hasegawa, Yoshio Kawai, Katsuya Takemura
  • Patent number: 7741007
    Abstract: The present invention provides a chemically amplified resist composition comprising: (A) a salt represented by the formula (1) wherein R21, Q1, Q2, and A+ defined in the specification; (B) a salt represented by the formula (II): wherein R22, Q3, Q4, and A?+ are defined in the specification; and (C) a resin which contains a structural unit having a structural unit having 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: December 3, 2007
    Date of Patent: June 22, 2010
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Satoshi Yamaguchi, Satoshi Yamamoto, Nobuo Ando
  • Patent number: 7718344
    Abstract: A resist composition, includes: (B) a polymer having a group capable of decomposing under an action of an acid and having a weight average molecular weight of 1,000 to 5,000, of which solubility in an alkali developer increases under an action of an acid; and (Z) a compound containing a sulfonium cation having a structure represented by formula (Z-1): wherein Y1 to Y13 each independently represents a hydrogen atom or a substituent, and adjacent members of Y1 to Y13 may combine with each other to form a ring; and Z represents a single bond or a divalent linking group.
    Type: Grant
    Filed: September 28, 2007
    Date of Patent: May 18, 2010
    Assignee: FUJIFILM Corporation
    Inventors: Sou Kamimura, Kenji Wada, Yasutomo Kawanishi
  • Patent number: 7713679
    Abstract: There is provided a compound represented by a general formula (B1-1) shown below, an acid generator composed of the above compound, a resist composition containing an acid generator composed of the above compound, and a method of forming a resist pattern: (wherein RX represents a hydrocarbon group which may contain a substituent group; Q1 represents an alkylene group of 1 to 12 carbon atoms which may contain a substituent group, or a single bond; n represents an integer of 0 or 1; Y1 represents an alkylene group of 1 to 4 carbon atoms, or a fluorinated alkylene group of 1 to 4 carbon atoms; and A+ represents an organic cation which contains a nitrogen atom).
    Type: Grant
    Filed: October 14, 2008
    Date of Patent: May 11, 2010
    Inventors: Keita Ishiduka, Yoshiyuki Utsumi, Akiya Kawaue, Takehiro Seshimo, Hideo Hada
  • Patent number: 7709179
    Abstract: A chemically amplified negative resist composition is provided in addition to a method of forming a resist pattern from which a desirable pattern shape can be obtained.
    Type: Grant
    Filed: April 7, 2006
    Date of Patent: May 4, 2010
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventor: Jun Iwashita
  • Patent number: 7682772
    Abstract: A compound represented by general formula (I); and a compound represented by general formula (b1-1). [Chemical Formula 1] X-Q1-Y1—SO3?M+??(I) X-Q1-Y1—SO3?A+??(b1-1) wherein Q1 represents a divalent linkage group or a single bond; Y1 represents an alkylene group which may have a substituent or a fluorinated alkylene group which may have a substituent; X represents a cyclic group of 3 to 30 carbon atoms which may have a substituent, and has an —SO2— bond in the structure thereof; M+ represents an alkali metal ion; and A+ represents an organic cation.
    Type: Grant
    Filed: November 5, 2008
    Date of Patent: March 23, 2010
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Takehiro Seshimo, Yoshiyuki Utsumi, Akiya Kawaue, Hideo Hada, Hiroaki Shimizu, Tsuyoshi Nakamura
  • Patent number: 7674567
    Abstract: A positive resist composition comprising: at least one compound selected from a compound capable of generating an acid represented by the formula (I) as defined herein upon irradiation with actinic rays or radiation and a compound capable of generating an acid represented by the following formula (II) upon irradiation with actinic rays or radiation; and a compound capable of generating an acid represented by the formula (III) as defined herein upon irradiation with actinic rays or radiation.
    Type: Grant
    Filed: September 20, 2006
    Date of Patent: March 9, 2010
    Assignee: FUJIFILM Corporation
    Inventors: Kei Yamamoto, Shinichi Kanna
  • Patent number: 7670746
    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: March 2, 2010
    Assignee: FUJIFILM Corporation
    Inventor: Kunihiko Kodama
  • Patent number: 7618765
    Abstract: A positive resist composition comprises (A) a resin component which becomes soluble in an alkaline developer under the action of an acid, and (B) an acid generator which is a specific sulfonium salt compound. The resin (A) is a polymer comprising tertiary alkyl protective group units having a hydrophobic tetracyclo[4.4.0.12,5.17,10]dodecane structure, di- or trihydroxyadamantyl units, and monocyclic lactone units.
    Type: Grant
    Filed: January 2, 2008
    Date of Patent: November 17, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Tsunehiro Nishi, Seiichiro Tachibana, Katsuhiro Kobayashi
  • Patent number: 7615323
    Abstract: Lithographic printing plate precursor comprising (a) a lithographic substrate with a hydrophilic surface and (b) a radiation-sensitive coating on the hydrophilic surface comprising (i) one or more types of monomers and/or oligomers and/or polymers, each comprising at least one ethylenically unsaturated group accessible to a free radical polymerization, (ii) at least one sensitizer, and at least one coinitiator capable of forming free radicals together with the sensitizer (ii); characterized in that the at least one sensitizer is an oligomeric or polymeric compound comprising the following structural unit (Formula (I)), wherein ?1 is an aromatic or heteroaromatic unit or a combination of the two so that a conjugated n-system is present between the two groups Z in structure (I), each Z independently represents a heteroatom, each R1 and R2 is independently selected from a halogen atom, an alkyl, aryl, alkylaryl or aralkyl group, a group —NR3R4 and a group —OR5, each R3, R4 and R5 is independently selected from a
    Type: Grant
    Filed: November 11, 2005
    Date of Patent: November 10, 2009
    Assignee: Kodak Graphic Communications, GmbH
    Inventors: Bernd Strehmel, Harald Baumann, Udo Dwars, Detlef Pietsch, Axel Draber, Michael Mursal
  • Patent number: 7615330
    Abstract: A positive resist composition containing a compound including a sulfonium cation having a structure represented by the formula (Z-I) as defined herein, a low molecular weight compound which increases solubility in an alkali developing solution by an action of an acid, and a compound which generates a compound having a structure represented by the formula (A-I) as defined herein upon irradiation of an actinic ray or a radiation.
    Type: Grant
    Filed: March 26, 2007
    Date of Patent: November 10, 2009
    Assignee: FUJIFILM Corporation
    Inventors: Sou Kamimura, Tomoya Sasaki, Yasutomo Kawanishi, Kenji Wada
  • Patent number: 7611822
    Abstract: The present invention provides a salt represented by the formula (I): wherein Q1 and Q2 each independently represent a fluorine atom or a C1-C6 perfluoroalkyl group, T represents a methylene group or a carbonyl group, R represents an adamantyl group substituted with at least one selected from the group consisting of a C1-C4 alkyl group, a C1-C4 alkoxy group, a hydroxyl group, a hydroxymethyl group, a cyano group and an oxo group, and A+ represents an organic counter ion. The present invention further provides a chemically amplified resist composition comprising the salt represented by the above-mentioned formula (I).
    Type: Grant
    Filed: July 22, 2008
    Date of Patent: November 3, 2009
    Assignee: Sumitomo Chemical Company, Limited
    Inventor: Ichiki Takemoto
  • Patent number: 7579132
    Abstract: The present invention provides a salt represented by the formula (I): wherein X represents an n-valent connecting group, Y1 and Y2 each independently represent a fluorine atom or a C1-C6 perfluoroalkyl group, n represents 2 or 3, and A+ represents an organic counter ion. The present invention further provides a chemically amplified resist composition comprising the salt represented by the above-mentioned formula (I).
    Type: Grant
    Filed: June 4, 2007
    Date of Patent: August 25, 2009
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yukako Harada, Isao Yoshida, Satoshi Yamaguchi
  • Patent number: 7575850
    Abstract: The present invention provides a chemically amplified resist composition comprising: a resin which comprises a structural unit having an acid-labile group and a structural unit represented by the formula (I): wherein R1 represents a hydrogen atom or a methyl group, ring X represents a C3-C30 cyclic hydrocarbon group in which one —CH2— is substituted with —COO—, and at least one hydrogen atom in the C3-C30 cyclic hydrocarbon group may be substituted, and p represents an integer of 1 to 4, and which itself is insoluble or poorly soluble in an alkali aqueous solution but becomes soluble in an alkali aqueous solution by the action of an acid, and at least two salts selected from a salt represented by the formula (II): wherein Y1 and Y2 each independently represent a fluorine atom or a C1-C6 perfluoroalkyl group, A+ represents an organic counter ion and R21 represents a C1-C30 hydrocarbon group which may be substituted and at least one —CH2— in the C1-C30 hydrocarbon group may be substituted with —CO
    Type: Grant
    Filed: January 28, 2008
    Date of Patent: August 18, 2009
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yoshiyuki Takata, Satoshi Yamamoto, Satoshi Yamaguchi
  • Patent number: 7572570
    Abstract: The present invention provides a chemically amplified resist composition comprising: (A) a resin which comprises (a) a structural unit having an acid-labile group, (b) a structural unit having at least one hydroxyl group, (c) a structural unit having at least one lactone structure, and (d) a structural unit represented by the formula (Ia) or (Ib): wherein R1 represents a hydrogen atom or a methyl group, R3 represents a methyl group, n represents an integer of 0 to 14, and Z represents a single bond or —[CH2]k—COO—, and (B) at least one acid generator.
    Type: Grant
    Filed: March 20, 2008
    Date of Patent: August 11, 2009
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yusuke Fuji, Yoshiyuki Takata
  • Patent number: 7566522
    Abstract: The present invention provides a chemically amplified resist composition comprising a resin which comprises a structural unit having an acid-labile group and a structural unit represented by the formula (I): wherein R1 represents a hydrogen atom or a methyl group, ring X represents a C3-C30 cyclic hydrocarbon group in which one —CH2— is substituted with —COO—, and at least one hydrogen atom in the C3-C30 cyclic hydrocarbon group may be substituted, and p represents an integer of 1 to 4, and which itself is insoluble or poorly soluble in an alkali aqueous solution but becomes soluble in an alkali aqueous solution by the action of an acid, and a salt represented by the formula (II): wherein Y1 and Y2 each independently represent a fluorine atom or a C1-C6 perfluoroalkyl group, A+ represents an organic counter ion, and R21 represents a C1-C30 hydrocarbon group which may be substituted and at least one —CH2— in the C1-C30 hydrocarbon group may be substituted with —CO— or —O—.
    Type: Grant
    Filed: December 11, 2007
    Date of Patent: July 28, 2009
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yoshiyuki Takata, Takayuki Miyagawa, Kunishige Edamatsu