Halogen Attached Indirectly To The Sulfonate Group By Acyclic Nonionic Bonding Patents (Class 562/113)
  • 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: 8283492
    Abstract: A process for manufacture of hydrofluoroalkanesulfonic acid with at least one hydrogen bonded to the carbon atom adjacent to the carbon atom bonded to the sulfonic acid group comprising: contacting a fluoroolefin with sulfite in an aqueous solution adjusted to about pH 4 to pH 12; removing water from the solution to form a solid; directly treating the solid with oleum; and distilling the hydrofluoroalkanesulfonic acid therefrom. Also a process for manufacture of potassium hydrofluoroalkanesulfonate in high purity is described.
    Type: Grant
    Filed: January 20, 2011
    Date of Patent: October 9, 2012
    Assignee: E I du Pont de Nemours and Company
    Inventors: Mark Andrew Harmer, Christopher P. Junk, Zoe Schnepp
  • 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
  • Publication number: 20120244690
    Abstract: According to certain embodiments, a resist is placed over the surface of a semiconductor structure, wherein the resist covers a portion of the semiconductor structure. Dopants are implanted into the semiconductor structure using an ion implantation beam in regions of the semiconductor structure not covered by the resist. Due to exposure to the ion implantation beam, at least a portion of the resist is converted by exposure to the ion beam to contain an inorganic carbonized material. The semiconductor structure with resist is contacted with a superacid composition containing a superacid species to remove the resist containing inorganic carbonized materials from the semiconductor structure.
    Type: Application
    Filed: March 23, 2011
    Publication date: September 27, 2012
    Applicant: TOSHIBA AMERICA ELECTRONIC COMPONENTS, INC.
    Inventor: Yoshihiro Uozumi
  • Publication number: 20120245658
    Abstract: The present invention relates inter alia to compositions comprising ionic species and electroluminescent compounds, formulations and devices comprising them, and their use for the treatment and/or prophylaxis of therapeutic diseases and/or cosmetic conditions.
    Type: Application
    Filed: November 11, 2010
    Publication date: September 27, 2012
    Applicant: Merck Patent GmbH
    Inventors: Junyou Pan, Herwig Buchholz, Ewald Aydt
  • Publication number: 20120237874
    Abstract: According to one embodiment, an actinic-ray- or radiation-sensitive resin composition includes any of the compounds (A) of general formula (I) below that when exposed to actinic rays or radiation, generates an acid and a resin (B) whose rate of dissolution into an alkali developer is increased by the action of an acid. (The characters used in general formula (I) have the meanings mentioned in the description.
    Type: Application
    Filed: May 31, 2012
    Publication date: September 20, 2012
    Applicant: FUJIFILM CORPORATION
    Inventors: Shuhei Yamaguchi, Akinori Shibuya
  • 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: 8241831
    Abstract: An acid generating agent represented by the following formula (1) or (2) is provided, which is included in chemically amplified resist compositions: wherein in the formula (1) and (2), X represents an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms and selected from alkyl, haloalkyl and alkylsulfonyl, which may have at least one hydrogen atom substituted by an ether group, an ester group, a carbonyl group, an acetal group, a nitrile group, a cyano group, a hydroxyl group, a carboxyl group or an aldehyde group, or represents a perfluoroalkyl group having 1 to 4 carbon atoms; R6 represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or a heteroatom selected from nitrogen, sulfur, fluorine and oxygen; m is an integer from 0 to 2; and A+ is an organic counterion.
    Type: Grant
    Filed: September 5, 2008
    Date of Patent: August 14, 2012
    Assignee: Korea Kumho Petrochemical Co., Ltd.
    Inventors: Sung-Do Jung, Jin-Ho Kim, Jung-Hoon Oh, Hyun-Soon Lim
  • Patent number: 8227169
    Abstract: There are provided a compound preferable as an acid generator for a resist composition, an acid generator including the compound, a resist composition containing the acid generator, and a method of forming a resist pattern using the resist composition, and the compound is represented by general formula (b1-12) shown below: R2—CH2—O—Y1—SO3?A+??(b1-12) wherein R2 represents a monovalent aromatic organic group; Y1 represents an alkylene group of 1 to 4 carbon atoms which may be fluorinated; and A+ represents a cation.
    Type: Grant
    Filed: April 4, 2008
    Date of Patent: July 24, 2012
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Akiya Kawaue, Yoshiyuki Utsumi, Takehito Seo, Hideo Hada, Kotaro Endo, Daisuke Kawana, Yasuhiro Yoshii, Tsuyoshi Kurosawa
  • 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
  • Publication number: 20120141939
    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: Application
    Filed: November 30, 2011
    Publication date: June 7, 2012
    Inventors: James W. Thackeray, Suzanne M. Coley, James F. Cameron, Paul J. LaBeaume, Ahmad E. Madkour, Owendi Ongayi, Vipul Jain
  • Publication number: 20120107210
    Abstract: The invention generally relates to methods of selectively removing lithium from various liquids, methods of producing high purity lithium carbonate, methods of producing high purity lithium hydroxide, and methods of regenerating resin.
    Type: Application
    Filed: November 28, 2011
    Publication date: May 3, 2012
    Applicant: Simbol Mining Corp.
    Inventors: Stephen Harrison, Robert Blanchet
  • Publication number: 20120100056
    Abstract: The invention generally relates to methods of selectively removing lithium from various liquids, methods of producing high purity lithium carbonate, methods of producing high purity lithium hydroxide, and methods of regenerating resin.
    Type: Application
    Filed: November 28, 2011
    Publication date: April 26, 2012
    Applicant: Simbol Mining Corp.
    Inventors: Stephen Harrison, Robert Blanchet
  • Patent number: 8163461
    Abstract: The invention provides various photoacid generator compounds and ionic components thereof. Photoresist compositions that include the ions and non-ionic photoacid generator compounds are also provided. The invention further provides methods of making and using the photoacid generator compounds and photoresist compositions disclosed herein. The compounds and compositions are useful as photoactive components in chemically amplified resist compositions for use in, for example, various microfabrication applications.
    Type: Grant
    Filed: April 9, 2009
    Date of Patent: April 24, 2012
    Assignee: Cornell Research Foundation, Inc.
    Inventors: Christopher K. Ober, Yi Yi
  • Patent number: 8148044
    Abstract: A positive photosensitive composition includes at least one compound that when exposed to actinic rays or radiation, generates any of the sulfonic acids of general formula (I) and a resin whose solubility in an alkali developer is increased by the action of an acid, wherein each of X1 and X2 independently represents a fluorine atom or a fluoroalkyl group, R1 represents a group with a polycyclic structure, provided that the polycyclic structure may have a substituent, and R2 represents a hydrogen atom, a chain alkyl group, a monocyclic alkyl group, a group with a polycyclic structure or a monocyclic aryl group, provided that each of the chain alkyl group, monocyclic alkyl group, polycyclic structure and monocyclic aryl group may have a substituent, and provided that R1 and R2 may be bonded to each other to thereby form a polycyclic structure.
    Type: Grant
    Filed: October 29, 2009
    Date of Patent: April 3, 2012
    Assignee: Fujifilm Corporation
    Inventors: Shuhei Yamaguchi, Tomotaka Tsuchimura, Yuko Tada
  • Publication number: 20120065425
    Abstract: A process for the purification of fluoroalkanesulfonate salt comprising (a) contacting a mixture of said salt and an inorganic salt contaminant with a solvent to selectively dissolve said fluoroalkanesulfonate salt in solution, and (b) isolating the solution, to yield a fluoroalkanesulfonate salt containing less than 500 micrograms of inorganic salt contaminant per gram of fluoroalkanesulfonate salt, or containing less than a maximum of 0.3% by weight of individual solvent.
    Type: Application
    Filed: September 10, 2010
    Publication date: March 15, 2012
    Applicant: E. I. DU PONT DE NEMOURS AND COMPANY
    Inventors: ALLEN CAPRON SIEVERT, LEE GRANT SPRAGUE, JAMES A. SCHULTZ, KATELYN RAE WALCK
  • Patent number: 8114570
    Abstract: Photoacid generators generate sulfonic acids of formula (1a) upon exposure to high-energy radiation. ROC(?O)R1—COOCH2CF2SO3?H+??(1a) RO is OH or C1-C20 organoxy, R1 is a divalent C1-C20 aliphatic group or forms a cyclic structure with RO. The photoacid generators are compatible with resins and can control acid diffusion and are thus suited for use in chemically amplified resist compositions.
    Type: Grant
    Filed: March 24, 2009
    Date of Patent: February 14, 2012
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Takeshi Kinsho, Takeru Watanabe, Koji Hasegawa, Masaki Ohashi
  • Patent number: 8105748
    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 C2-C20 hydrocarbon group having cyclic structure, 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: October 16, 2009
    Date of Patent: January 31, 2012
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Masaki Ohashi, Youichi Ohsawa, Takeshi Kinsho, Jun Hatakeyama, Seiichiro Tachibana
  • 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
  • Publication number: 20110269989
    Abstract: A method for halogenating, sulfonating, or sulfo-halogenating a feed comprising paraffin, by subjecting a mixture comprising the feed and a reagent selected from the group consisting of sulfonating agents, halogenating agents, and combinations thereof to a shear rate of at least 20,000 s?1 to produce a high-shear treated product; cooling the high shear-treated product by heat exchange with a heat transfer medium, to produce a cooled product; and separating the high shear-treated product into an offgas and a liquid product comprising at least one selected from the group consisting of sulfonated paraffins, halogenated paraffins, and sulfo-halogenated paraffins. A high shear system for the production of halogenated, sulfonated, or sulfo-halogenated paraffin is also provided.
    Type: Application
    Filed: March 2, 2011
    Publication date: November 3, 2011
    Applicant: H R D Corporation
    Inventors: Abbas HASSAN, Krishnan Viswanathan, Rayford G. Anthony, Gregory Borsinger, Aziz Hassan
  • Publication number: 20110269990
    Abstract: In this method for producing a perfluoroalkylsulfonic acid salt, there is provided a method for producing a perfluoroalkylsulfonic acid salt with a low fluorine content, which is a simple method to achieve a high yield, wherein a solution is formed by adding, to at least one compound selected from perfluoroalkylsulfonic acid salts represented by a general formula RfSO3.M (wherein Rf represents a perfluoroalkyl group of 1 to 4 carbon atoms, and M represents Li, Na or K), an organic solvent which is capable of dissolving the compound, and an adsorbent having a capacity to adsorb fluorine ions is added to the solution.
    Type: Application
    Filed: January 5, 2010
    Publication date: November 3, 2011
    Applicants: Mitsubishi Materials Electronic Chemicals Co., Ltd, MITSUBISHI MATERIALS CORPORATION
    Inventors: Tsunetoshi Honda, Hiroyuki Yatsuyanagi
  • Patent number: 8026391
    Abstract: This method for producing a potassium perfluoroalkanesulfonate includes an electrochemical fluorination step in which an alkanesulfonyl halide compound is subjected to electrochemical fluorination in anhydrous hydrogen fluoride, thereby to generate a production gas containing perfluoroalkanesulfonyl fluoride as the main component. In addition, for example, the methods may include a gas absorption step in which the production gas is reacted with an aqueous solution of potassium hydroxide, thereby to generate a gas absorbed solution containing potassium perfluoroalkanesulfonate, a purification step in which impurities such as potassium fluoride, potassium hydroxide, and potassium sulfate, are removed, and a concentration and collection step in which the aqueous solution from which the impurities are removed is concentrated and dried.
    Type: Grant
    Filed: September 29, 2006
    Date of Patent: September 27, 2011
    Assignees: Mitsubishi Materials Corporation, Mitsubishi Materials Electronic Chemicals Co., Ltd.
    Inventors: Masakazu Uotani, Hiroyuki Yatsuyanagi, Tsunetoshi Honda
  • Publication number: 20110215274
    Abstract: Ferroelectric liquid crystal compositions including organic ion pair compounds wherein image sticking is reduced or eliminated. Use of the ferroelectric liquid crystal compositions in a ferroelectric liquid crystal display device allows for rapid image refresh rates without required a DC-balancing algorithm. The organic ion pair compounds provide electrical resistivity values for the compositions that result in reduced image sticking when the compositions are used in FLC display devices.
    Type: Application
    Filed: January 14, 2011
    Publication date: September 8, 2011
    Inventors: Cory Pecinovsky, William Thurmes, Brion C. Koprowski
  • Publication number: 20110200508
    Abstract: The invention generally relates to methods of selectively removing lithium from various liquids, methods of producing high purity lithium carbonate, methods of producing high purity lithium hydroxide, and methods of regenerating resin.
    Type: Application
    Filed: February 17, 2011
    Publication date: August 18, 2011
    Applicant: Simbol Mining Corp.
    Inventors: Stephen Harrison, Robert Blanchet
  • Publication number: 20110152540
    Abstract: A photoacid generator which can generate an acid efficiently when energy was absorbed, is excellent in the developing property and can form fine patterns, and a cationic polymerization initiator excellent in curability are provided; and a resist composition and a cationically polymerizable composition using them are provided. An aromatic sulfonium salt compound represented by the General Formula (I) below: (wherein each of E1 to E4 independently represents a substituent represented by the General Formula (II) below or the General Formula (III) below). Preferably, in the General Formula (I), r and s are 0; m and n are 0; or n and r are 0, and more preferably, one of m and s in the General Formula (I) is 1.
    Type: Application
    Filed: August 4, 2008
    Publication date: June 23, 2011
    Inventors: Tesuyuki Nakayashiki, Kentaro Kimura
  • 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: 7919226
    Abstract: Sulfonate salts have the formula: CF3—CH(OCOR)—CF2SO3?M+ wherein R is C1-C20 alkyl or C6-C14 aryl, and M+ is a lithium, sodium, potassium, ammonium or tetramethylammonium ion. Onium salts, oximesulfonates and sulfonyloxyimides and other compounds derived from these sulfonate salts are effective photoacid generators in chemically amplified resist compositions.
    Type: Grant
    Filed: August 13, 2008
    Date of Patent: April 5, 2011
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Takeru Watanabe, Takeshi Kinsho, Katsuhiro Kobayashi
  • Patent number: 7901867
    Abstract: Compounds of the formula (I), (II), (III), (IV) and wherein, R is hydrogen, C1-C20alkyl; C2-C20alkyl interrupted by one or more O; is -L-X—R2 or -L-R2; R1 has for example one of the meanings as given for R; R2 is a monovalent sensitizer or photoinitiator moiety; Ar1 and Ar2 for example independently of one another are phenyl substituted by C1-C20alkyl, halogen or OR3; or are unsubstituted naphthyl, anthryl, phenanthryl or biphenylyl; or are naphthyl, anthryl, phenanthryl or biphenylyl substituted by C1-C20alkyl, OH or OR3; or are —Ar4-A-Ar3; Ar3 is unsubstituted phenyl naphthyl, anthryl, phenanthryl or biphenylyl; or is phenyl, naphthyl, anthryl, phenanthryl or biphenylyl substituted by C1-C20alkyl, OR3 or benzoyl; Ar4 is phenylene, naphthylene, anthrylene or phenanthrylene; A is a direct bond, S, O or C1-C20alkylene; X is CO, C(O)O, OC(O), O, S or NR3; L is C1-C20alkylene or C2-C20alkylene interrupted by one or more O; R3 is C1-C20alkyl or C1-C20hydroxyalkyl; and Y is an anion, are suitable as photolatent ac
    Type: Grant
    Filed: June 21, 2006
    Date of Patent: March 8, 2011
    Assignee: BASF SE
    Inventors: Jean-Pierre Wolf, Attila Latika, Jean-Luc Birbaum, Stephan Ilg, Pascal Hayoz
  • Patent number: 7901871
    Abstract: A composition containing a photoacid generator monomer and surfactant, and a method for synthesizing a compound on a substrate using the composition are provided. The method includes bonding a layer of first molecules having an acid labile protecting group to a solid substrate; coating a layer of the photoacid generator monomer composition according to the present invention on the layer of first molecules; exposing the composition layer to light and then heat-treating to remove the acid labile protecting group from the first molecules corresponding to the exposed portion; washing and removing the composition layer from the exposed and unexposed portions; and bonding second molecules to the exposed first molecules.
    Type: Grant
    Filed: January 9, 2008
    Date of Patent: March 8, 2011
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Sung-ouk Jung, Seung-ju Seo, Jae-chan Park
  • Patent number: 7897807
    Abstract: A process for manufacture of hydrofluoroalkanesulfonic acid with at least one hydrogen bonded to the carbon atom adjacent to the carbon atom bonded to the sulfonic acid group comprising: contacting a fluoroolefin with sulfite in an aqueous solution adjusted to about pH 4 to pH 12; removing water from the solution to form a solid; directly treating the solid with oleum; and distilling the hydrofluoroalkanesulfonic acid therefrom. Also a process for manufacture of potassium hydrofluoroalkanesulfonate in high purity is described.
    Type: Grant
    Filed: February 22, 2010
    Date of Patent: March 1, 2011
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Mark Andrew Harmer, Christopher P. Junk, Zoe Schnepp
  • Publication number: 20110034724
    Abstract: The present invention relates to a method for preparing a salt of trifluoromethanesulphinic acid termed “triflinic acid”. More specifically, the invention relates to a method for preparing a highly pure triflinic acid salt.
    Type: Application
    Filed: November 25, 2008
    Publication date: February 10, 2011
    Applicant: Rhodia Operations
    Inventors: Vincent Schanen, Olivier Buisine, François Metz, Bernard Besson
  • 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
  • Publication number: 20100324330
    Abstract: The composition for preventing development-defects containing (1) an ammonium salt, a tetraalkylammonium salt or a C1 to C4 alkanolamine salt of C4 to C15 perfluoroalkylcarboxylic acid, C4 to C10 perfluoroalkylsulfonic acid and perfluoroadipic acid, or (2) a fluorinated alkyl quaternary ammonium salt of inorganic acid, wherein said surfactant is formed at the equivalent ratio of acid to base of 1:1-1:3 is applied on a chemically amplified photoresist coating on a substrate having a diameter of 8 inches or more. The chemically amplified photoresist coating is baked before and/or after applying the composition for preventing development-defects described above. Then, the baked coating with the development-defect preventing composition coating is exposed to light, post-exposure-baked, and developed.
    Type: Application
    Filed: August 10, 2010
    Publication date: December 23, 2010
    Inventors: Yasushi Akiyama, Yusuke Takano, Kiyohisa Takahashi, Sung-Eun Hong, Tetsuo Okayasu
  • 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
  • Publication number: 20100145093
    Abstract: A process for manufacture of hydrofluoroalkanesulfonic acid with at least one hydrogen bonded to the carbon atom adjacent to the carbon atom bonded to the sulfonic acid group comprising: contacting a fluoroolefin with sulfite in an aqueous solution adjusted to about pH 4 to pH 12; removing water from the solution to form a solid; directly treating the solid with oleum; and distilling the hydrofluoroalkanesulfonic acid therefrom. Also a process for manufacture of potassium hydrofluoroalkanesulfonate in high purity is described.
    Type: Application
    Filed: February 22, 2010
    Publication date: June 10, 2010
    Applicant: E. I. DU PONT DE NEMOURS AND COMPANY
    Inventors: Mark Andrew Harmer, Christopher P. Junk, Zoe Schnepp
  • Patent number: 7728166
    Abstract: The subject matter of the invention is a process for the production of metal salts of trifluoromethane sulphonic acid by reacting trifluoromethane sulphonic acid with a metal alcoholate and the use thereof as esterification catalyst and/or transesterification catalyst for the production of hydroxycarboxylic acid esters.
    Type: Grant
    Filed: November 18, 2004
    Date of Patent: June 1, 2010
    Assignee: Sasol Solvents Germany GmbH
    Inventors: Peter Finmans, Detlef Hoell, Hans-Jurgen Vossler, Martina Rozek, Michael James Green, Rafael Roggenbuck
  • Patent number: 7683209
    Abstract: A process for manufacture of hydrofluoroalkanesulfonic acid with at least one hydrogen bonded to the carbon atom adjacent to the carbon atom bonded to the sulfonic acid group comprising: contacting a fluoroolefin with sulfite in an aqueous solution adjusted to about pH 4 to pH 12; removing water from the solution to form a solid; directly treating the solid with oleum; and distilling the hydrofluoroalkanesulfonic acid therefrom. Also a process for manufacture of potassium hydrofluoroalkanesulfonate in high purity is described.
    Type: Grant
    Filed: June 6, 2006
    Date of Patent: March 23, 2010
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Mark Andrew Harmer, Christopher P. Junk, Zoe Schnepp
  • 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
  • Publication number: 20090269673
    Abstract: The invention relates to a method for producing perfluoroalkanesulfonic acid esters and for further transforming the same into the salts thereof. The invention also relates to the use of the produced compounds in electrolytes, batteries, capacitors, supercapacitors, and galvanic cells.
    Type: Application
    Filed: July 8, 2009
    Publication date: October 29, 2009
    Inventors: Nikolai Ignatyev, Michael Schmidt, Udo Heider, Peter Sartori, Andry Kucheryna
  • Patent number: 7601480
    Abstract: The present application relates to a compound of formula where X is selected from the group CF3SO3, C4F9SO3, N(SO2C2F5)2, N(SO2CF3SO2C4F9), N(SO2C3F7)2, N(SO2C4F9)2, CF3CHFO(CF2)2SO3, and CH3CH2CH2O(CF2)4SO3. A photoresist composition comprising a polymer containing an acid labile group, the above compounds, and one or more additional photoacid generators is also provided for.
    Type: Grant
    Filed: December 20, 2006
    Date of Patent: October 13, 2009
    Assignee: AZ Electronic Materials USA Corp.
    Inventors: M. Dalil Rahman, Takanori Kudo
  • 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: 7579499
    Abstract: Hexafluoroisobutylene and its higher homologs are easily reacted with SO3 to give fluorosulfates of the formula CH2?C(R)CF2OSO2F, wherein R is a linear branched or cyclic fluoroalkyl group comprised of 1 to 10 carbon atoms and may contain ether oxygen. These compounds react under mild conditions with many nucleophiles to give CH2?C(R)CF2X, where X is derived from the nucleophile. This reaction provides a route to many substituted hexafluoroisobutylenes, which copolymerize easily with other fluoro- and hydrocarbon monomers such as vinylidene fluoride and ethylene.
    Type: Grant
    Filed: March 22, 2007
    Date of Patent: August 25, 2009
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Victor Filippovich Cherstkov, Nina Ivanova Delyagina, Viacheslav A. Petrov, Paul R. Resnick
  • Patent number: 7569326
    Abstract: A sulfonium salt having a polymerizable anion generates a strong sulfonic acid upon exposure to high-energy radiation so that it facilitates effective scission of acid labile groups in chemically amplified resist compositions. It is useful as a monomer from which a base resin for use in radiation-sensitive resist compositions is derived.
    Type: Grant
    Filed: October 25, 2007
    Date of Patent: August 4, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Masaki Ohashi, Seiichiro Tachibana, Jun Hatakeyama, Takeru Watanabe
  • Publication number: 20090143613
    Abstract: This method for producing a potassium perfluoroalkanesulfonate includes an electrochemical fluorination step in which an alkanesulfonyl halide compound is subjected to electrochemical fluorination in anhydrous hydrogen fluoride, thereby to generate a production gas containing perfluoroalkanesulfonyl fluoride as the main component. In addition, for example, the methods may include a gas absorption step in which the production gas is reacted with an aqueous solution of potassium hydroxide, thereby to generate a gas absorbed solution containing potassium perfluoroalkanesulfonate, a purification step in which impurities such as potassium fluoride, potassium hydroxide, and potassium sulfate, are removed, and a concentration and collection step in which the aqueous solution from which the impurities are removed is concentrated and dried.
    Type: Application
    Filed: September 29, 2006
    Publication date: June 4, 2009
    Applicant: Mitsubishi Materials Corporation
    Inventors: Masakazu Uotani, Hiroyuki Yatsuyanagi, Tsunetoshi Honda
  • Publication number: 20090137840
    Abstract: The invention provides a process for the preparation of fluorinated alkanesulfonic acid anhydrides by contacting alkanesulfonic acids with phosphorus pentoxide, the phosphorus pentoxide being provided as a dispersion in an inert oil. The invention also provides novel fluorinated alkanesulfonic acid anhydrides including 2-hydrotetrafluoroethanesulfonic acid anhydride.
    Type: Application
    Filed: November 20, 2008
    Publication date: May 28, 2009
    Applicant: E. I. Du Pont de Nemours and Company
    Inventors: Christopher P. Junk, Vsevolod Rostovtsev, Allen Capron Sievert, Lee G. Sprague
  • Publication number: 20090131684
    Abstract: A photoacid generator represented by Formula 1 or Formula 2: wherein R1, R2, and R3 are each independently a C1-C10 alkyl group, X is a C3-C20 alicyclic hydrocarbon group forming a ring with S+, and at least one CH2 group in the alicyclic hydrocarbon group may be replaced with at least one selected from the group consisting of S, O, NH, a carbonyl group, and R5—S+A?, where R5 is a C1-C10 alkyl group, and A? is a counter-ion.
    Type: Application
    Filed: September 29, 2008
    Publication date: May 21, 2009
    Inventors: Yool Kang, Hak-won Kim, Weoun-ju Kim, Seong-woon Choi, Hyun-woo Kim, Hai-sub Na, Kyoung-taek Kim
  • Patent number: 7531689
    Abstract: Hexafluoroisobutylene and its higher homologs are easily reacted with SO3 to give fluorosulfates of the formula CH2?C(R)CF2OSO2F, wherein R is a linear branched or cyclic fluoroalkyl group comprised of 1 to 10 carbon atoms and may contain ether oxygen. These compounds react under mild conditions with many nucleophiles to give CH2?C(R)CF2X, where X is derived from the nucleophile. This reaction provides a route to many substituted hexafluoroisobutylenes, which copolymerize easily with other fluoro- and hydrocarbon monomers such as vinylidene fluoride and ethylene.
    Type: Grant
    Filed: March 22, 2007
    Date of Patent: May 12, 2009
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Victor Filippovich Cherstkov, Nina Ivanova Delyagina, Richard E. Fernandez, Viacheslav A. Petrov, Weiming Qiu, Paul R. Resnick
  • Patent number: 7524609
    Abstract: A photosensitive composition, which comprises (A) a compound capable of generating an organic acid represented by formula (I) upon irradiation with actinic ray or radiation: Z—A—X—B—R—(Y)n??(I) wherein Z represents an organic acid group; A represents a divalent linking group; X represents a divalent linking group having a hetero atom; B represents an oxygen atom or —N(Rx)—; Rx represents a hydrogen atom or a monovalent organic group; R represents a monovalent organic group substituted with Y, and when B represents —N(Rx)—, R and Rx may be bonded to each other to form a cyclic structure; Y represents —COOH or —CHO, and when a plurality of Y's are present, the plurality of Y's may be the same or different; and n represents an integer of from 1 to 3.
    Type: Grant
    Filed: March 9, 2007
    Date of Patent: April 28, 2009
    Assignee: FUJIFILM Corporation
    Inventor: Kenji Wada