Polycyclo Alicyclic Ring System Attached Directly Or Indirectly To The Sulfonate Group By Nonionic Bonding Patents (Class 562/100)
  • Patent number: 10407386
    Abstract: This invention relates to a method of preparing D-arginine, and more particularly to a method of preparing D-arginine by optically resolving DL-arginine using D-3-bromocamphor-8-sulfonic acid or a salt thereof as an optical resolving agent.
    Type: Grant
    Filed: September 6, 2016
    Date of Patent: September 10, 2019
    Assignee: AMINOLOGICS CO., LTD.
    Inventors: Il-Suk Byun, Jung-Ho Lee, Hye-Lim Ga, Won-Sup Kim
  • Patent number: 10207986
    Abstract: Disclosed is a method of preparing D-arginine, wherein D-arginine is obtained by the optical resolution of DL-arginine using D-3-bromocamphor-10-sulfonic acid as an optical resolving agent.
    Type: Grant
    Filed: August 5, 2015
    Date of Patent: February 19, 2019
    Assignee: Aminiologics Co., Ltd.
    Inventors: Il-Suk Byun, Won-Sup Kim, Hye-Lim Ga, Jung-Ho Lee
  • Patent number: 9477149
    Abstract: A photoresist composition containing (A) a polymer having a structural unit (I) that includes an acid-labile group, and (I) a compound represented by the following formula (1). In the following formula (1), R1, R2, R3 and R represent a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms. X represents a single bond, an oxygen atom or —NRa—. Ra represents a hydrogen atom, a hydroxy group or a monovalent organic group having 1 to 20 carbon atoms, and optionally taken together represents a ring structure by binding with R each other. A? represents —SO3? or —CO2?. M+ represents a monovalent onium cation.
    Type: Grant
    Filed: September 19, 2014
    Date of Patent: October 25, 2016
    Assignee: JSR CORPORATION
    Inventors: Hayato Namai, Norihiko Ikeda, Takanori Kawakami
  • Patent number: 9314027
    Abstract: Functionalized fullerenes are used in a method of combating fungal growth on surfaces and treating fungal diseases of patients. Surfaces that can be treated by the materials comprising an effective amount of functionalized fullerenes include those of fruits, vegetables, harvested grains, plants, or plant seeds. The method of combating fungal growth on a surface can be augmented but is not dependent on irradiation of the surface by light. Functional fullerenes are employed in various dosage forms such as topical, ingestible or administration.
    Type: Grant
    Filed: April 1, 2010
    Date of Patent: April 19, 2016
    Assignee: UNIVERSITY OF FLORIDA RESEARCH FOUNDATION, INC.
    Inventors: Vijay Krishna, Brij M. Moudgil, Benjamin L. Koopman
  • Patent number: 9200098
    Abstract: A radiation-sensitive composition includes a photoacid generator shown by a general formula (0-1a). Each of R0 individually represents a substituted or unsubstituted organic group which includes a carbon atom, a hydrogen atom, and an oxygen atom, and which includes at least one ester bond, and M+ represents a monovalent onium cation. A compound is shown by a general formula (0). R represents a substituted or unsubstituted organic group which includes a carbon atom, a hydrogen atom, and an oxygen atom, and which includes at least one ester bond, and M+ represents a monovalent onium cation.
    Type: Grant
    Filed: March 8, 2012
    Date of Patent: December 1, 2015
    Assignee: JSR CORPORATION
    Inventor: Ken Maruyama
  • Patent number: 9085463
    Abstract: Provided herein are water-soluble, functionalized fullerenes, and processes for producing water-soluble, functionalized fullerenes. The process includes sulfonating a fullerene in an acidic solution comprising sulfuric acid to produce a sulfonated fullerene, isolating the sulfonated fullerene from the acidic solution without neutralizing the acidic solution, reacting the sulfonated fullerene with hydrogen peroxide to form a reaction product, and isolating a polyhydroxylated fullerene from the reaction product produced from reacting the sulfonated fullerene with the hydrogen peroxide. The process of producing water-soluble fullerenes further includes functionalizing a polyhydroxylated fullerene with one or more pendant functional groups by reacting the polyhydroxylated fullerene with one or more functional group precursors.
    Type: Grant
    Filed: January 17, 2012
    Date of Patent: July 21, 2015
    Assignee: Marelle, LLC
    Inventors: Mark Farrell, Michelle Guaragno
  • 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: 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: 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: 8962233
    Abstract: According to one embodiment, an actinic-ray- or radiation-sensitive resin composition includes an arylsulfonium salt that when exposed to actinic rays or radiation, generates an acid, the arylsulfonium salt containing at least one aryl ring on which there are a total of one or more electron donating groups, the acid generated upon exposure to actinic rays or radiation having a volume of 240 ?3 or greater.
    Type: Grant
    Filed: January 28, 2011
    Date of Patent: February 24, 2015
    Assignee: FUJIFILM Corporation
    Inventors: Takeshi Kawabata, Tomotaka Tsuchimura, Takayuki Ito
  • 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
  • Publication number: 20150037734
    Abstract: A resist composition containing a compound represented by general formula (m0), wherein R1 and R2 each independently represents an aryl group which may have a substituent, an alkyl group which may have a substituent, or an alkenyl group which may have a substituent, provided that R1 and R2 may be mutually bonded to form a ring with the sulfur atom; R3 represents an aromatic hydrocarbon group which may have a substituent, an alkenyl group which may have a substituent, or an alkynyl group which may have a substituent; V1 represents a single bond or an alkylene group, provided that, when R3 is an aromatic hydrocarbon group which may have a substituent, V1 is an alkylene group; and X0? represents a monovalent organic anion.
    Type: Application
    Filed: July 23, 2014
    Publication date: February 5, 2015
    Inventors: Takashi Nagamine, Yoshitaka Komuro, Masatoshi Arai, Yoshiyuki Utsumi
  • 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
  • Publication number: 20140356787
    Abstract: A resist composition comprising a compound (m0) (wherein Rb1 represents an electron withdrawing group; Rb2 and Rb3 each independently represents an aryl group, an alkyl group or an alkenyl group, provided that Rb2 and Rb3 may be mutually bonded to form a ring with the sulfur atom; and X0? represents a monovalent counteranion).
    Type: Application
    Filed: May 30, 2014
    Publication date: December 4, 2014
    Applicant: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Yoshitaka Komuro, Takaaki Kaiho, Toshiaki Hato, Akiya Kawaue, Junichi Tsuchiya, Yoshiyuki Utsumi
  • Patent number: 8900794
    Abstract: A photoacid generator compound has the formula (I): [A-(CHR1)p]k-(L)-(CH2)m—(C(R2)2)n—SO3?Z+??(I) wherein A is a substituted or unsubstituted, monocyclic, polycyclic, or fused polycyclic C5 or greater cycloaliphatic group optionally comprising O, S, N, F, or a combination comprising at least one of the foregoing, R1 is H, a single bond, or a substituted or unsubstituted C1-30 alkyl group, wherein when R1 is a single bond, R1 is covalently bonded to a carbon atom of A, each R2 is independently H, F, or C1-4 fluoroalkyl, wherein at least one R2 is not hydrogen, L is a linking group comprising a sulfonate group, a sulfonamide group, or a C1-30 sulfonate or sulfonamide-containing group, Z is an organic or inorganic cation, p is an integer of 0 to 10,k is 1 or 2, m is an integer of 0 or greater, and n is an integer of 1 or greater.
    Type: Grant
    Filed: September 28, 2012
    Date of Patent: December 2, 2014
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: Emad Aqad, Cheng-Bai Xu, Mingqi Li, Shintaro Yamada, William Williams, III
  • 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: 8889901
    Abstract: A photoacid generator represented by the following formula (1), a method for producing the photoacid generator, and a resist composition containing the photoacid generator are provided. wherein in the formula (1), Y, X, R1, R2, n1, n2 and A+ have the same meanings as defined in the detailed description of the invention. The photoacid generator can maintain an appropriate contact angle at the time of ArF liquid immersion lithography, can reduce defects occurring during liquid immersion lithography, and has excellent solubility in resist solvents and excellent compatibility with resins. Furthermore, the photoacid generator can be produced by an efficient and simple method using an epoxy compound that is industrially easily available.
    Type: Grant
    Filed: February 7, 2012
    Date of Patent: November 18, 2014
    Assignee: Korea Kumho Petrochemical Co., Ltd.
    Inventors: Jung Hoon Oh, Dae Kyung Yoon, Yong Hwa Hong, Seung Duk Cho
  • Publication number: 20140329746
    Abstract: Methods, compounds, pharmaceutical compositions and kits are described for treating or preventing amyloid-related disease.
    Type: Application
    Filed: July 16, 2014
    Publication date: November 6, 2014
    Inventors: Xianqi Kong, Xinfu Wu, Abderrahim Bouzide, Isabelle Valade, David Migneault, Francine Gervais, Daniel Delorme, Benoit Bachand, Mohamed Atfani, Sophie Levesque, Bita Samim
  • 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: 8703387
    Abstract: A resist composition comprising a base component (A) which exhibits changed solubility in a developing solution under action of acid and an acid-generator component (B) which generates acid upon exposure, the acid-generator component (B) comprising an acid generator (B1) composed of a compound represented by general formula (b1-1) shown below [wherein, X represents a cyclic group of 3 to 30 carbon atoms which may have a substituent, provided that a ring skelton of the cyclic group contains an —SO2— bond or an —O—SO2— bond, and at least one carbon atom which is not adjacent to the —SO2— bond or the —O—SO2— bond has an oxygen atom as a substituent; Q1 represents a divalent linking 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; and A+ represents an organic cation].
    Type: Grant
    Filed: May 23, 2012
    Date of Patent: April 22, 2014
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Akiya Kawaue, Yoshiyuki Utsumi
  • Publication number: 20140107027
    Abstract: Methods, compounds, pharmaceutical compositions and kits are described for treating or preventing amyloid-related disease.
    Type: Application
    Filed: December 18, 2013
    Publication date: April 17, 2014
    Applicant: BHI LIMITED PARTNERSHIP
    Inventors: Xianqi Kong, David Migneault, Isabelle Valade, Xinfu Wu, Francine Gervais
  • 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: 20130244185
    Abstract: A radiation-sensitive resin composition includes an acid generating agent to generate an organic acid by irradiation with a radioactive ray. The organic acid has a cyclic hydrocarbon group and an organic group including a bond that is cleavable by an acid or a base to produce a polar group. The organic acid is preferably represented by a following formula (I). Z represents an organic acid group. R1 represents an alkanediyl group, wherein a part or all of hydrogen atoms of the alkanediyl group represented by R1 are optionally substituted by a fluorine atom. X represents a single bond, O, OCO, COO, CO, SO3 or SO2. R2 represents a cyclic hydrocarbon group. R3 represents a monovalent organic group having a functional group represented by a following formula (x). n is an integer of 1 to 3.
    Type: Application
    Filed: September 14, 2012
    Publication date: September 19, 2013
    Applicant: JSR Corporation
    Inventors: Yasuhiko MATSUDA, Takanori Kawakami
  • 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: 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
  • Publication number: 20130090314
    Abstract: Provided herein are novel solid state forms of tapentadol salts, process for their preparation, pharmaceutical compositions, and method of treating thereof. The tapentadol salts include an L-(?)-camphorsulfonate salt, a dibenzoyl-(L)-tartrate salt, a dibenzoyl-(D)-tartrate salt, a malate salt, a maleate salt, or a salicylate salt.
    Type: Application
    Filed: September 11, 2012
    Publication date: April 11, 2013
    Applicant: ACTAVIS GROUP PTC EHF
    Inventors: Mayur Devjibhai Khunt, Sandipan Prabhurao Bondge, Nitin Sharadchandra Pradhan, Depashri Vikas Ahirao
  • 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
  • Publication number: 20130084525
    Abstract: A photoacid generator compound has the formula (I): [A-(CHR1)p]k-(L)-(CH2)m—(C(R2)2)n—SO3?Z+??(I) wherein A is a substituted or unsubstituted, monocyclic, polycyclic, or fused polycyclic C5 or greater cycloaliphatic group optionally comprising O, S, N, F, or a combination comprising at least one of the foregoing, R1 is H, a single bond, or a substituted or unsubstituted C1-30 alkyl group, wherein when R1 is a single bond, R1 is covalently bonded to a carbon atom of A, each R2 is independently H, F, or C1-4 fluoroalkyl, wherein at least one R2 is not hydrogen, L is a linking group comprising a sulfonate group, a sulfonamide group, or a C1-30 sulfonate or sulfonamide-containing group, Z is an organic or inorganic cation, p is an integer of 0 to 10, k is 1 or 2, m is an integer of 0 or greater, and n is an integer of 1 or greater.
    Type: Application
    Filed: September 28, 2012
    Publication date: April 4, 2013
    Applicant: ROHM AND HAAS ELECTRONIC MATERIALS LLC
    Inventor: Rohm and Haas Electronic Materials LLC
  • Publication number: 20130078579
    Abstract: A radiation-sensitive resin composition includes an acid generating agent to generate a compound represented by a following formula (1) by irradiation with a radioactive ray. In the formula (1), R1 represents a monovalent organic group having 1 to 20 carbon atoms. R2 represents a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms. The compound represented by the formula (1) is preferably a compound represented by a following formula (1-1). In the formula (1-1), R2 is as defined in the above formula (1). X represents an electron attractive group. R3 represents a monovalent organic group having 1 to 20 carbon atoms.
    Type: Application
    Filed: September 26, 2012
    Publication date: March 28, 2013
    Applicant: JSR CORPORATION
    Inventor: JSR CORPORATION
  • Publication number: 20130065186
    Abstract: A radiation-sensitive resin composition includes an acid generating agent to generate an organic acid by irradiation with a radioactive ray. The organic acid has a cyclic hydrocarbon group and an organic group including a bond that is cleavable by an acid or a base to produce a polar group. The organic acid is preferably represented by a following formula (I). Z represents an organic acid group. R2 represents an alkanediyl group, wherein a part or all of hydrogen atoms of the alkanediyl group represented by R1 are optionally substituted by a fluorine atom. X represents a single bond, O, OCO, COO, CO, SO3 or SO2. R2 represents a cyclic hydrocarbon group. R3 represents a monovalent organic group having a functional group represented by a following formula (x). n is an integer of 1 to 3.
    Type: Application
    Filed: September 14, 2012
    Publication date: March 14, 2013
    Applicant: JSR Corporation
    Inventors: Yasuhiko MATSUDA, Takanori Kawakami
  • Patent number: 8367297
    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) containing a compound having a cation moiety represented by general formula (I) (in the formula, R5 represents a hydrogen atom or an organic group of 1 to 30 carbon atoms which may have a substituent; and Q5 represents a single bond or a divalent linking group).
    Type: Grant
    Filed: December 9, 2009
    Date of Patent: February 5, 2013
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Akiya Kawaue, Yoshiyuki Utsumi, Shinichi Hidesaka, Natsuko Maruyama
  • 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
  • Patent number: 8288077
    Abstract: The object of the present invention is to provide a chemically amplified resist composition excellent in a resolution and a mask error enhancement factor. By employing the salt represented by the formulae (A1) as an acid generator of a resist composition, the above mentioned object is achieved. wherein Z+ represents an organic cation, Q1 and Q2 each independently represent a fluorine atom or a perfluoroalkyl group, Ra2 represents a divalent alicyclic hydrocarbon group pr the like, Ra2 represents an elimination group represented by the formulae (II-1) or (II-2). In the formulae (II-1) or (II-2), Ra3 and Ra4 each independently represent a hydrogen atom or an aliphatic hydrocarbon group, Ra5 represents an aliphatic hydrocarbon group, Ra6 represents a divalent aliphatic hydrocarbon group, and Ra7 represents an aliphatic hydrocarbon group.
    Type: Grant
    Filed: July 27, 2010
    Date of Patent: October 16, 2012
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Isao Yoshida, Satoshi Yamaguchi
  • 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: 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: 20120203030
    Abstract: A photoacid generator represented by the following formula (1), a method for producing the photoacid generator, and a resist composition containing the photoacid generator are provided. wherein in the formula (1), Y, X, R1, R2, n1, n2 and A+ have the same meanings as defined in the detailed description of the invention. The photoacid generator can maintain an appropriate contact angle at the time of ArF liquid immersion lithography, can reduce defects occurring during liquid immersion lithography, and has excellent solubility in resist solvents and excellent compatibility with resins. Furthermore, the photoacid generator can be produced by an efficient and simple method using an epoxy compound that is industrially easily available.
    Type: Application
    Filed: February 7, 2012
    Publication date: August 9, 2012
    Applicant: Korea Kumho Petrochemical Co., Ltd.
    Inventors: Jung Hoon OH, Dae Kyung Yoon, Yong Hwa Hong, Seung Duk Cho
  • Publication number: 20120172606
    Abstract: A sulfonium compound represented by formula (1), a photo-acid generator, and a method for producing a sulfonium compound are provided: wherein X represents an electron-donating group; R1 and R2 each represent an alkyl group, a cycloalkyl group, or the like; R3 and R4 each represent an arylene group or a heteroarylene group; R5 and R6 each represent an alkyl group, a cycloalkyl group, or the like; and A? and B? are anions that are different from each other. The sulfonium compound, when used as a photo-acid generator, can produce a uniform and excellent resist pattern.
    Type: Application
    Filed: December 30, 2011
    Publication date: July 5, 2012
    Applicant: Korea Kumho Petrochemical Co., Ltd.
    Inventors: Hyun Sang JOO, Dong Chul Seo, Dae Kyung Yoon, Dae Hyeon Shin
  • Publication number: 20120164582
    Abstract: A radiation-sensitive composition includes a photoacid generator shown by a general formula (0-1a). Each of R0 individually represents a substituted or unsubstituted organic group which includes a carbon atom, a hydrogen atom, and an oxygen atom, and which includes at least one ester bond, and M+ represents a monovalent onium cation. A compound is shown by a general formula (0). R represents a substituted or unsubstituted organic group which includes a carbon atom, a hydrogen atom, and an oxygen atom, and which includes at least one ester bond, and M+ represents a monovalent onium cation.
    Type: Application
    Filed: March 8, 2012
    Publication date: June 28, 2012
    Applicant: JSR Corporation
    Inventor: Ken MARUYAMA
  • Patent number: 8202731
    Abstract: Novel fluorescent dyes are disclosed for use in analyte detection. In particular, mono- and bis-substituted HPTS dyes and methods of making them are provided.
    Type: Grant
    Filed: June 3, 2010
    Date of Patent: June 19, 2012
    Assignee: Glumetrics, Inc.
    Inventor: Jeff T. Suri
  • Patent number: 8173354
    Abstract: A sulfonium salt having a triphenylsulfonium cation and a sulfite anion within the molecule is best suited as a photoacid generator in chemically amplified resist compositions. Upon exposure to high-energy radiation, the sulfonium salt generates a sulfonic acid, which facilitates efficient scission of acid labile groups in chemically amplified positive resist compositions. Because of substantial non-volatility under high vacuum conditions in the EB or EUV lithography, the risk of the exposure tool being contaminated is minimized.
    Type: Grant
    Filed: July 7, 2010
    Date of Patent: May 8, 2012
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Masaki Ohashi