The Chalcogen, X, Is In A -c(=x)- Group Patents (Class 562/109)
  • Patent number: 10954473
    Abstract: Aqueous surfactant compositions comprising one or more alpha-sulfo fatty acid disalt (A) of general formula (I) R1CH(SO3M1)COOM2??(I), in which the radical R1 is a linear or branched alkyl or alkenyl radical having 6 to 18 carbon atoms and the radicals M1 and M2, independently of each other, are selected from H, Li, Na, K, Ca/2, Mg/2, ammonium, and alkanolamine, one or more sulfoketone (B) selected from compounds (F) and compounds (G) wherein the compounds (F) have general formula (VI) R6CH2—CO—CHR7(SO3M8)??(VI), in which the radicals R6 and R7, independently of each other, are a linear or branched alkyl radical having 6 to 18 carbon atoms and the radical M8 is selected from H, Li, Na, K, Ca/2, Mg/2, ammonium, and alkanolamine, and the compounds (G) have general formula (VII) (SO3M9)R8CH—CO—CHR9(SO3M10)??(VII), in which the radicals R8 and R9, independently of each other, are a linear or branched alkyl radical having 6 to 18 carbon atoms and the radicals M9 and M10, independently of each other, are s
    Type: Grant
    Filed: May 11, 2017
    Date of Patent: March 23, 2021
    Assignee: BASF SE
    Inventors: Claudia Brunn, Ansgar Behler, Hans-Christian Raths, Detlev Stanislowski, Gerhard Hermanns
  • Patent number: 10945936
    Abstract: Aqueous surfactant compositions containing one or more alpha-sulfo fatty acid disalt (A) of general formula (I), R1CH(SO3M1)COOM2??(I), in which the radical R1 is a linear or branched alkyl or alkenyl radical having 6 to 18 carbon atoms and the radicals M1 and M2, independently of one another, are selected from the group consisting of H, Li, Na, K, Ca/2, Mg/2, ammonium, and alkanolamine, one or more alkanolamide (B) selected from the group of compounds of general formula (IIa), (IIb) and (IIc), R13—CO—NR14R15??(IIa) R13—CO—NR14R16??(IIb) R13—CO—NR14R17??(IIc) wherein the radical R13 in compounds (IIa) is a linear or branched alkyl radical having 6 to 18 carbon atoms and the radicals R14 and R15, independently of each other, are a linear or branched hydroxyalkyl group having 1 to 4 carbon atoms; wherein the radical R13 in compounds (IIb) is a linear or branched alkyl radical having 6 to 18 carbon atoms, the radical R14 is a linear or branched hydroxyalkyl group having 1 to 4 carbon atoms and the radic
    Type: Grant
    Filed: May 11, 2017
    Date of Patent: March 16, 2021
    Assignee: BASF SE
    Inventors: Claudia Brunn, Ansgar Behler
  • Patent number: 10933006
    Abstract: Aqueous surfactant compositions comprising one or more alpha-sulfo fatty acid disalt (A) of general formula (I) R1CH(SO3M1)COOM2??(I), in which the radical R1 is a linear or branched alkyl or alkenyl radical having 6 to 18 carbon atoms and the radicals M1 and M2, independently of each other, are selected from H, Li, Na, K, Ca/2, Mg/2, ammonium, and alkanolamine, one or more sulfosuccinate (B) of general formula (II) R31—O—CO—CH(SO3M16)—CH2—COOM17??(II) wherein the radical R31 is a linear or branched alkyl or alkenyl radical having 6 to 22 carbon atoms or an alkoxylated linear or branched alkyl or alkenyl radical having 6 to 22 carbon atoms and the radicals M16 and M17, independently of each other, are selected from the group comprising H, Li, Na, K, Ca/2, Mg/2, ammonium and alkanolamines, and water. The compositions have good foaming ability, good skin compatibility, and a pleasant sensory feel to the foam, and are suitable for cosmetic products detergents, and cleaners.
    Type: Grant
    Filed: May 11, 2017
    Date of Patent: March 2, 2021
    Assignee: BASF SE
    Inventors: Claudia Brunn, Ansgar Behler
  • Patent number: 9040220
    Abstract: A resist composition including a base component which exhibits changed solubility in an alkali developing solution under action of acid and an acid-generator component which generates acid upon exposure, the acid-generator including an acid generator consisting of a compound represented by general formula (b1-1) shown below: In which RX represents a hydrocarbon group which may have a substituent exclusive of a nitrogen atom; each of Q2 and Q3 independently represents a single bond or a divalent linkage group; Y1 represents an alkylene group or fluorinated alkyl group of 1 to 4 carbon atoms; and Z+ represents an organic cation exclusive of an ion represented by general formula (w-1).
    Type: Grant
    Filed: March 2, 2012
    Date of Patent: May 26, 2015
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hideo Hada, Yoshiyuki Utsumi, Keita Ishiduka, Kensuke Matsuzawa, Fumitake Kaneko, Kyoko Ohshita, Hiroaki Shimizu, Yasuhiro Yoshii
  • Patent number: 9034556
    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, the acid-generator component (B) including an acid generator (B1) consisting of a compound represented by general formula (b1-1) shown below: wherein RX represents a hydrocarbon group which may have a substituent exclusive of a nitrogen atom; each of Q2 and Q3 independently represents a single bond or a divalent linkage group; Y1 represents an alkylene group or fluorinated alkyl group of 1 to 4 carbon atoms; and Z+ represents an organic cation exclusive of an ion represented by general formula (w-1).
    Type: Grant
    Filed: December 18, 2008
    Date of Patent: May 19, 2015
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hideo Hada, Yoshiyuki Utsumi, Keita Ishiduka, Kensuke Matsuzawa, Fumitake Kaneko, Kyoko Ohshita, Hiroaki Shimizu, Yasuhiro Yoshii
  • Patent number: 9023584
    Abstract: A radiation-sensitive composition includes a compound represented by a formula (1), and a polymer having a structural unit that includes an acid-labile group. In the formula (1), R1 represents a group having a polar group; n is an integer of 1 to 4, wherein, in a case where R1 is present in a plurality of number, the plurality of R1s are identical or different, and optionally at least two R1s taken together represent a cyclic structure; A represents an alicyclic hydrocarbon group having a valency of (n+1); and M+ represents a monovalent onium cation.
    Type: Grant
    Filed: May 24, 2013
    Date of Patent: May 5, 2015
    Assignee: JSR Corporation
    Inventor: Ken Maruyama
  • Patent number: 9017924
    Abstract: A resist composition which generates acid upon exposure and exhibits changed solubility in a developing solution under action of acid, including a base component (A) which exhibits changed solubility in a developing solution under action of acid, the base component (A) including a polymeric compound (A1) containing a structural unit (a0) represented by general formula (a0-1) shown below. In the formula, W1 represents a group which is formed by polymerization reaction of a group containing a polymerizable group; Y1 and Y2 each independently represents a divalent linking group; Y3 represents a carbonyl group or an alkylene group; R2 and R3 each independently represents a fluorine atom or a fluorinated alkyl group; Mm+ represents an organic cation having a valency of m; and m represents an integer of 1 or more.
    Type: Grant
    Filed: March 4, 2014
    Date of Patent: April 28, 2015
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Daichi Takaki, Yoshiyuki Utsumi
  • Patent number: 9017931
    Abstract: A negative pattern is formed by coating a resist composition comprising a polymer comprising recurring units having a tertiary ester type acid labile group having a plurality of methyl or ethyl groups on alicycle and an acid generator onto a substrate, prebaking, exposing to high-energy radiation, baking, and developing in an organic solvent developer so that the unexposed region of resist film is dissolved away and the exposed region of resist film is not dissolved. The resist composition exhibits a high dissolution contrast during organic solvent development and forms a fine hole or trench pattern of dimensional uniformity.
    Type: Grant
    Filed: August 16, 2013
    Date of Patent: April 28, 2015
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Koji Hasegawa, Jun Hatakeyama, Masayoshi Sagehashi, Teppei Adachi
  • Patent number: 9005872
    Abstract: A resist composition including a base component (A) which exhibits changed solubility in a developing solution under action of acid, a basic-compound component (C) and an acid-generator component (B) which generates acid upon exposure, the component (B) including a compound represented by formula (b1), and the component (C) including at least one compound represented by formulas (c1) to (c3) (wherein Z1 represents a ring skeleton-containing hydrocarbon group, Q1 represents a divalent linking group containing oxygen, Y1 represents a fluorinated alkylene group, M+ represents an organic cation, R1 represents a fluorinated alkyl group or a hydrocarbon group, L1+ and L2+ represents a sulfonium or an iodonium, Z2 represents a hydrogen atom or a hydrocarbon group, Y2 represents a single bond or a divalent linking group containing no fluorine, R2 represents an organic group, Y3 represents an alkylene group or an arylene group; and Rf represents a fluorine-containing hydrocarbon group).
    Type: Grant
    Filed: February 16, 2012
    Date of Patent: April 14, 2015
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hiroaki Shimizu, Sho Abe, Hideto Nito
  • Patent number: 8993212
    Abstract: A resist composition according to the present invention includes at least a base resin, a photoacid generator and a solvent, wherein the photoacid generator comprises a fluorine-containing sulfonic acid salt of the following general formula (4). In the formula, X independently represents a hydrogen atom or a fluorine atom; n represents an integer of 1 to 6; R1 represents a hydrogen atom, or an alkyl, alkenyl, oxoalkyl, aryl or aralkyl group; any of hydrogen atoms on carbons in R1 may be substituted with a substituent; R2 represents RAO or RBRCN; and A represents a divalent group. This fluorine-containing sulfonic acid salt can serve as a photoacid generator having high solubility in a resist solvent and thus can suitably be used for a resist composition such that the resist composition shows high resolution, wide DOF, small LER and high sensitivity to form a good pattern shape in lithographic processes.
    Type: Grant
    Filed: October 14, 2011
    Date of Patent: March 31, 2015
    Assignee: Central Glass Company, Limited
    Inventors: Ryozo Takihana, Satoru Narizuka
  • Patent number: 8993210
    Abstract: A salt represented by the formula (I): wherein R1 and R2 each independently represent a fluorine atom or a C1-C6 perfluoroalkyl group, X1 represents a C1-C17 divalent saturated hydrocarbon group which can have one or more fluorine atoms and in which one or more —CH2— can be replaced by —O— or —CO—, R3 represents a group having a cyclic ether structure, and Z1+ represents an organic cation.
    Type: Grant
    Filed: February 15, 2011
    Date of Patent: March 31, 2015
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Hiromu Sakamoto
  • Patent number: 8956799
    Abstract: A photoacid generator includes those of formula (I): wherein each Ra in formula 1 is independently H, F, a C1-10 nonfluorinated organic group, C1-10 fluorinated organic group, or a combination comprising at least one of the foregoing, provided at least one Ra is F or a C1-10 fluorinated organic group, the C1-10 fluorinated and nonfluorinated organic groups each optionally comprising O, S, N, or a combination comprising at least one of the foregoing heteroatoms; L1 is a linking group comprising a heteroatom comprising O, S, N, F, or a combination comprising at least one of the foregoing; G+ is an onium salt of the formula (II): wherein in formula (II), X is S or I, each R0 is independently C1-30 alkyl group; a polycyclic or monocyclic C3-30 cycloalkyl group; a polycyclic or monocyclic C4-30 aryl group; or a combination comprising at least one of the foregoing, provided at least one R0 is substituted where each R0 is a C6 monocyclic aryl group, and wherein when X is I, a is 2, and where X is S, a is 3,
    Type: Grant
    Filed: December 12, 2012
    Date of Patent: February 17, 2015
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: Emad Aqad, Cheng-Bai Xu, Mingqi Li, William Williams, III
  • Patent number: 8932797
    Abstract: A photoacid generator compound has formula (I): G+Z???(I) wherein G has formula (II): In formula (II), X is S or I, each R0 is commonly attached to X and is independently C1-30 alkyl; polycyclic or monocyclic C3-30 cycloalkyl; polycyclic or monocyclic C6-30 aryl; or a combination comprising at least one of the foregoing groups. G has a molecular weight greater than 263.4 g/mol, or less than 263.4 g/mol. One or more R0 groups are further attached to an adjacent R0 group, a is 2 or 3, wherein when X is I, a is 2, or when X is S, a is 2 or 3. Z in formula (I) comprises the anion of a sulfonic acid, a sulfonimide, or a sulfonamide. A photoresist and coated film also includes the photoacid generator, and a method of forming an electronic device uses the photoresist.
    Type: Grant
    Filed: November 30, 2011
    Date of Patent: January 13, 2015
    Assignees: Dow Global Technologies LLC, Rohm and Haas Electronic Materials LLC
    Inventors: James W. Thackeray, Suzanne M. Coley, James F. Cameron, Paul J. LaBeaume, Ahmad E. Madkour, Owendi Ongayi, Vipul Jain
  • Patent number: 8921029
    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, 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: December 30, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Yukako Anryu, Shingo Fujita
  • Patent number: 8889333
    Abstract: A salt represented by 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 a methylene group may be replaced by an oxygen atom or a carbonyl group, L2 and L3 respectively represent a single bond or a C1-C6 divalent saturated alkyl group in which a methylene group may be replaced by an oxygen atom or a carbonyl group, ring W1 and ring W2 respectively represent a C3-C36 hydrocarbon ring, R1 and R2 respectively represent a hydrogen atom or C1-C6 alkyl group, R3 represents C1-C6 alkyl group, t represents an integer of 0 to 2 and Z+ represents an organic counter ion.
    Type: Grant
    Filed: April 10, 2012
    Date of Patent: November 18, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Isao Yoshida, Yuko Yamashita
  • Patent number: 8871423
    Abstract: A photoresist composition for fabricating a probe array is provided. The photoresist composition includes a photoacid generator having an onium salt and an i-line reactive sensitizer.
    Type: Grant
    Filed: January 28, 2011
    Date of Patent: October 28, 2014
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Hyo-Jin Yun, Jae-Ho Kim, Young-Ho Kim, Boo-Deuk Kim, Jin-A Ryu, Myung-Sun Kim, Se-Kyung Baek, Soo-Kyung Kim, Ji-Yun Ham
  • Patent number: 8853441
    Abstract: A sulfonium compound represented by the following formula (1), a photoacid generator containing the sulfonium compound, and a resist composition containing the photoacid generator are provided: wherein X represents an electron donor group; R1 and R2 each independently represent an alkyl group or the like; R4 to R6 each independently represent an alkyl group, or the like; R3 represents a cyclic alkenediyl group or the like; and ?A represents an anion. The sulfonium compound has a photon yield that is controllable by introducing different absorbers to the cation region in one molecule, can address the inconvenience of using a mixture of different photoacid generators when the sulfonium compound is applied as a photoacid generator, has excellent miscibility in a resist, and has enhanced resolution and line edge roughness.
    Type: Grant
    Filed: July 25, 2012
    Date of Patent: October 7, 2014
    Assignee: Korea Kumho Petrochemical Co., Ltd.
    Inventors: Jung Hoon Oh, Dae Kyung Yoon, Seung Duk Cho, So Jeong Park
  • Patent number: 8852846
    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-C20 divalent saturated hydrocarbon group in which one or more —CH2— can be replaced by —O— or —CO—, W represents a group represented by the formula (W1), (W2), (W3), (W4) or (W5): and Z+ represents an organic counter ion.
    Type: Grant
    Filed: April 4, 2012
    Date of Patent: October 7, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yukako Anryu, Koji Ichikawa
  • Patent number: 8846291
    Abstract: A resist composition including: a base component (A) which exhibits changed solubility in a developing solution under action of acid; a nitrogen-containing organic compound component (C) containing a compound (C1) represented by general formula (c1) shown below; and an acid generator component (B) which generates acid upon exposure, provided that the compound (C1) is excluded from the acid generator component (B): wherein RN represents a nitrogen-containing heterocyclic group which may have a substituent; X0 represents a linear or branched divalent aliphatic hydrocarbon group of 1 to 10 carbon atoms, a cyclic divalent aliphatic hydrocarbon group of 3 to 20 carbon atoms or a divalent aliphatic hydrocarbon group of 3 to 20 carbon having a cyclic partial structure, or any one of these groups in which some or all of the hydrogen atoms thereof have been substituted with fluorine atoms; and M+ represents an organic cation.
    Type: Grant
    Filed: December 6, 2011
    Date of Patent: September 30, 2014
    Assignee: Tokyo Ohka Kogyo Co. Ltd.
    Inventors: Yoshiyuki Utsumi, Kenichiro Miyashita, Akiya Kawaue
  • Patent number: 8835097
    Abstract: There is disclosed a sulfonium salt shown by the following general formula (1). There can be a sulfonium salt capable of introducing an acid-generating unit generating an acid having an appropriate acid strength and not impairing adhesion with a substrate into a base polymer; a polymer using the said sulfonium salt; a chemically amplified resist composition using the said polymer as a base polymer; and a patterning process using the said chemically amplified resist composition.
    Type: Grant
    Filed: May 21, 2012
    Date of Patent: September 16, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Daisuke Domon, Keiichi Masunaga, Satoshi Watanabe
  • Publication number: 20140255853
    Abstract: A resist composition which generates acid upon exposure and exhibits changed solubility in a developing solution under action of acid, including a base component (A) which exhibits changed solubility in a developing solution under action of acid, the base component (A) including a polymeric compound (A1) containing a structural unit (a0) represented by general formula (a0-1) shown below. In the formula, W1 represents a group which is formed by polymerization reaction of a group containing a polymerizable group; Y1 and Y2 each independently represents a divalent linking group; Y3 represents a carbonyl group or an alkylene group; R2 and R3 each independently represents a fluorine atom or a fluorinated alkyl group; Mm+ represents an organic cation having a valency of m; and m represents an integer of 1 or more.
    Type: Application
    Filed: March 4, 2014
    Publication date: September 11, 2014
    Applicant: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Daichi Takaki, Yoshiyuki Utsumi
  • Patent number: 8791293
    Abstract: According to the present invention, there is provided a fluorine-containing sulfonate resin having a repeating unit of the following general formula (3). In order to prevent deficiency such as roughness after pattern formation or failure in pattern formation, the fluorine-containing sulfonate resin incorporates therein a photoacid generating function and serves as a resist resin in which “a moiety capable of changing its developer solubility by the action of an acid” and “a moiety having a photoacid generating function” are arranged with regularity.
    Type: Grant
    Filed: August 2, 2012
    Date of Patent: July 29, 2014
    Assignee: Central Glass Company, Limited
    Inventors: Kazunori Mori, Satoru Narizuka, Fumihiro Amemiya, Masaki Fujiwara
  • Patent number: 8779183
    Abstract: An acid generating agent used for chemically amplified resist compositions is provided, which agent is represented by the following formula (1): wherein X represents a monocyclic or polycyclic hydrocarbon group having 3 to 30 carbon atoms, and having at least one hydrogen atom on the ring substituted by an alkyl or alkoxy group which may be unsubstituted or substituted with a group selected from an ether group, an ester group, a carbonyl group, an acetal group, an epoxy group, a nitrile group and an aldehyde group, or by a perfluoroalkyl group, a hydroxyalkyl group, or a cyano group; R6 is an alkyl group, an alkoxy group, or a heteroatom selected from the group consisting of N, S and F; m is an integer from 0 to 2; and A+ is an organic counterion.
    Type: Grant
    Filed: June 19, 2008
    Date of Patent: July 15, 2014
    Assignee: Korea Kumho Petrochemical Co., Ltd.
    Inventors: Jung-Hoon Oh, Dong-Cheol Seo, Hyun-Sang Joo, Chang-Soo Lee
  • Patent number: 8716519
    Abstract: The invention relates to novel cross-linkable monomers that may be polymerized with ethylenically unsaturated comonomers to form cross-linkable copolymers. Said copolymers may particularly be used in the form of aqueous dispersions as formaldehyde-free adhesives or as coatings with good water resistance.
    Type: Grant
    Filed: July 11, 2008
    Date of Patent: May 6, 2014
    Assignee: Celanese Emulsions GmbH
    Inventors: Martin Jakob, Stefan Nogai
  • 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: 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: 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: 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
  • Publication number: 20130209938
    Abstract: A resist composition according to the present invention includes at least a base resin, a photoacid generator and a solvent, wherein the photoacid generator comprises a fluorine-containing sulfonic acid salt of the following general formula (4). In the formula, X independently represents a hydrogen atom or a fluorine atom; n represents an integer of 1 to 6; R1 represents a hydrogen atom, or an alkyl, alkenyl, oxoalkyl, aryl or aralkyl group; any of hydrogen atoms on carbons in R1 may be substituted with a substituent; R2 represents RAO or RBRCN; and A represents a divalent group. This fluorine-containing sulfonic acid salt can serve as a photoacid generator having high solubility in a resist solvent and thus can suitably be used for a resist composition such that the resist composition shows high resolution, wide DOF, small LER and high sensitivity to form a good pattern shape in lithographic processes.
    Type: Application
    Filed: October 14, 2011
    Publication date: August 15, 2013
    Applicant: Central Glass Company, Ltd.
    Inventors: Ryozo Takihana, Satoru Narizuka
  • Patent number: 8465668
    Abstract: Surfactants with polyether sulfonate structure, which have a propanonylsulfonic acid group as a head group, a process for preparing such surfactants and their use for tertiary mineral oil extraction.
    Type: Grant
    Filed: October 15, 2008
    Date of Patent: June 18, 2013
    Assignee: BASF SE
    Inventors: Christian Bittner, Oetter Günter, Ulrich Steinbrenner, Jürgen Huff, Marcus Guzmann
  • Patent number: 8431326
    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—, ring W represents a C3-C36 aliphatic ring in which one or more —CH2— can be replaced by —O—, —S—, —CO— or —SO2— and in which one or more hydrogen atoms can be replaced by a hydroxyl group, a C1-C12 alkyl group, a C1-C12 alkoxy group, a C3-C12 alicyclic hydrocarbon group or a C6-C10 aromatic hydrocarbon group, Rf is independently in each occurrence a fluorine atom or a C1-C6 fluorinated alkyl group, n represents an integer of 1 to 10, and Z+ represents an organic counter ion.
    Type: Grant
    Filed: October 3, 2011
    Date of Patent: April 30, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Mitsuyoshi Ochiai, Takashi Hiraoka
  • Patent number: 8420294
    Abstract: The present invention provides a salt represented by the formula (I): wherein R1 and R2 independently each represent a C1-C6 alkyl group or R1 and R2 are bonded each other to form a C5-C20 aliphatic ring together with the carbon atom to which they are bonded, R3 and R4 independently each represent a fluorine atom or a C1-C6 perfluoroalkyl group, X1 represents a C1-C17 divalent saturated hydrocarbon group in which one or more —CH2— can be replaced by —O— or —CO— and which may be substituted with one or more fluorine atoms, and Z1+ represents an organic counter ion.
    Type: Grant
    Filed: November 25, 2011
    Date of Patent: April 16, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Yukako Anryu, Shingo Fujita
  • Patent number: 8318404
    Abstract: A salt represented by the formula (a1): wherein Q1 and Q2 each independently represent a fluorine atom or a C1-C4 perfluoroalkyl group, X1 represents —CO—O—Xa1— or —CH2—O—Xa2— wherein Xa1 and Xa2 independently each represent a C1-C15 alkylene group and one or more —CH2— in the alkylene group can be replaced by —O— or —CO—, Y1 represents a C3-C36 alicyclic hydrocarbon group or a C6-C24 aromatic hydrocarbon group, and the alicyclic hydrocarbon group and the aromatic hydrocarbon group can have one or more substituents, and one or more —CH2— in the alicyclic hydrocarbon group can be replaced by —O— or —CO—, and Z+ represents an organic cation.
    Type: Grant
    Filed: June 9, 2010
    Date of Patent: November 27, 2012
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Masako Sugihara, Hiromu Sakamoto
  • Publication number: 20120289738
    Abstract: A sulfonic acid derivative represented by the following general formula (1): [Chemical formula 1] RCOOCH2CH2CFHCF2SO3?M+??(1) where R represents a substituted or unsubstituted C1-30 linear, branched, or cyclic hydrocarbon group, or a substituted or unsubstituted C6-30 aryl group, and M+ represents a counter cation.
    Type: Application
    Filed: January 13, 2011
    Publication date: November 15, 2012
    Applicant: TOYO GOSEI CO., LTD.
    Inventors: Yasuhiro Hosoi, Yuzuru Kaneko
  • Patent number: 8283104
    Abstract: There is disclosed a sulfonate shown by the following general formula (2). R1—COOC(CF3)2—CH2SO3?M+??(2) (In the formula, R1 represents a linear, a branched, or a cyclic monovalent hydrocarbon group having 1 to 50 carbon atoms optionally containing a hetero atom. M+ represents a cation.) There can be provided: a novel sulfonate which is effective for a chemically amplified resist composition having a sufficiently high solubility (compatibility) in a resist solvent and a resin, a good storage stability, a PED stability, a further wider depth of focus, a good sensitivity, in particular a high resolution and a good pattern profile form; a photosensitive acid generator; a resist composition using this; a photomask blank, and a patterning process.
    Type: Grant
    Filed: February 16, 2010
    Date of Patent: October 9, 2012
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Masaki Ohashi, Takeshi Kinsho, Youichi Ohsawa
  • 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: 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
  • Publication number: 20120164580
    Abstract: A resist composition including a base component which exhibits changed solubility in an alkali developing solution under action of acid and an acid-generator component which generates acid upon exposure, the acid-generator including an acid generator consisting of a compound represented by general formula (b1-1) shown below: In which RX represents a hydrocarbon group which may have a substituent exclusive of a nitrogen atom; each of Q2 and Q3 independently represents a single bond or a divalent linkage group; Y1 represents an alkylene group or fluorinated alkyl group of 1 to 4 carbon atoms; and Z+ represents an organic cation exclusive of an ion represented by general formula (w-1).
    Type: Application
    Filed: March 2, 2012
    Publication date: June 28, 2012
    Applicant: TOKYO OHKA KOGYO CO., LTD.
    Inventors: Hideo Hada, Yoshiyuki Utsumi, Keita Ishiduka, Kensuke Matsuzawa, Fumitake Kaneko, Kyoko Ohshita, Hiroaki Shimizu, Yasuhiro Yoshii
  • 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: 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
  • Publication number: 20120009521
    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: Application
    Filed: September 15, 2011
    Publication date: January 12, 2012
    Applicant: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Akiya Kawaue, Yoshiyuki Utsumi, Takehiro Seshimo, Tsuyoshi Nakamura, Naoto Motoike, Hiroaki Shimizu, Kensuke Matsuzawa, Hideo Hada
  • Patent number: 8057985
    Abstract: A polymerizable anion-containing sulfonium salt having formula (1) is provided wherein R1 is H, F, methyl or trifluoromethyl, R2, R3 and R4 are C1-C10 alkyl, alkenyl or oxoalkyl or C6-C18 aryl, aralkyl or aryloxoalkyl, or two of R2, R3 and R4 may bond together to form a ring with S, A is a C1-C20 organic group, and n is 0 or 1. The sulfonium salt generates a very strong sulfonic acid upon exposure to high-energy radiation. A resist composition comprising a polymer derived from the sulfonium salt is also provided.
    Type: Grant
    Filed: August 27, 2009
    Date of Patent: November 15, 2011
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Masaki Ohashi, Takeshi Kinsho, Youichi Ohsawa, Jun Hatakeyama, Seiichiro Tachibana
  • Patent number: 8048604
    Abstract: Hydrofluoroalkanesulfonates of the general formula R—O—CXH—CX2—SO3M, where R is selected from the group consisting of alkyl groups, functionalized alkyl groups, and alkenyl groups; X is selected from the group consisting of hydrogen and fluorine with the proviso that at least one X is fluorine; and M is a cation, are made by reacting fluorovinyl ether with aqueous sulfite solution. Organic onium hydrofluoroalkanesulfonates are useful as ionic liquids and photoacid generators.
    Type: Grant
    Filed: October 21, 2010
    Date of Patent: November 1, 2011
    Assignee: E.I.du Pont de Nemours and Company
    Inventors: Christopher P. Junk, Mark Andrew Harmer, Andrew Edward Feiring, Frank Leonard Schadt, III, Zoe Schnepp
  • Publication number: 20110152537
    Abstract: The present invention relates to chemical compounds comprising a [Y(CHRa)n—CH(Ra)SO3]? anion, their preparation and application. The chemical compounds are preferably ionic liquids.
    Type: Application
    Filed: May 12, 2009
    Publication date: June 23, 2011
    Applicant: MERCK PATENT GESELLSCHAFT MIT BESCHRANKTER HAFTUNG
    Inventors: Peter Wasserscheid, Natalia Paape, Andreas Boesmann, Peter Schulz
  • Patent number: 7943370
    Abstract: A target substance detection element that can effectively prevent the nonspecific adsorption of a target substance or impurities and detects the target substance with high sensitivity, a target substance detection kit, and a structure constituting the target substance detection element. The structure has a substrate, polymers present on the substrate surface, and first target substance capturing molecules bonded to the polymers. The polymer is composed of a polymer of a carboxybetaine monomer represented by General Formula (1) below. The first target substance capturing molecules are bonded to some of the carboxyl groups of the polymers. A compound represented by General Formula (2) is bonded to at least some of the carboxyl groups, from among the carboxyl groups of the polymers, that are not bonded to the first target substance capturing molecules.
    Type: Grant
    Filed: August 7, 2008
    Date of Patent: May 17, 2011
    Assignee: Canon Kabushiki Kaisha
    Inventors: Masato Minami, Kazuhiro Ban
  • Publication number: 20110112306
    Abstract: A fluorine-containing sulfonic acid salt or a compound having a fluorine-containing sulfonic acid group, either of which having a structure represented by the following general formula (1), is provided. Such a salt or compound can act as a suitable photo-acid generator, and can form a resist pattern having excellent sensitivity, resolution and mask-dependence. [In general formula (1), R represents a substituted or unsubstituted linear or branched monovalent hydrocarbon group having 1 to 30 carbon atoms, a substituted or unsubstituted monovalent hydrocarbon group having 3 to 30 carbon atoms and a cyclic or a partially cyclic structure, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted monovalent heterocyclic organic group having 4 to 30 carbon atoms.
    Type: Application
    Filed: July 6, 2009
    Publication date: May 12, 2011
    Applicant: CENTRAL GLASS COMPANY, LIMITED
    Inventors: Masashi Nagamori, Masaki Fujiwara, Kazunori Mori, Satoru Narizuka
  • Publication number: 20110076312
    Abstract: An antimicrobial composition for coating a medical device. The antimicrobial composition includes a polymeric film forming material and an antimicrobial agent comprising a material selected from the group of extract of Houttuynia cordata, sodium houttuyfonate, sodium new houttuyfonate and mixtures thereof. A medical device having an antimicrobial composition that includes a material selected from the group of extract of Houttuynia cordata, sodium houttuyfonate, sodium new houttuyfonate and mixtures thereof and a method for making same are also provided.
    Type: Application
    Filed: September 29, 2009
    Publication date: March 31, 2011
    Applicant: ETHICON, INC.
    Inventors: Henry Pokropinski, JR., Jerome A. Fischer, Jerry Jonn, Huimin Wang, Stephen Rothenburger, Xintian Ming
  • Publication number: 20110021402
    Abstract: A solid detergent composition having the salt of an anionic surfactant and of a monopropanolamine counterion.
    Type: Application
    Filed: October 1, 2010
    Publication date: January 27, 2011
    Applicant: The Procter & Gamble Company
    Inventors: Ming Tang, Hiroshi Oh, Sen Liu, Victor Manuel Arredondo
  • 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