Halogen Attached Indirectly To The Sulfonate Group By Acyclic Nonionic Bonding Patents (Class 562/113)
-
Patent number: 8283104Abstract: 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: GrantFiled: February 16, 2010Date of Patent: October 9, 2012Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Masaki Ohashi, Takeshi Kinsho, Youichi Ohsawa
-
Patent number: 8283492Abstract: 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: GrantFiled: January 20, 2011Date of Patent: October 9, 2012Assignee: E I du Pont de Nemours and CompanyInventors: Mark Andrew Harmer, Christopher P. Junk, Zoe Schnepp
-
Patent number: 8278023Abstract: 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: GrantFiled: May 25, 2010Date of Patent: October 2, 2012Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Ichikawa, Masako Sugihara, Tatsuro Masuyama
-
Publication number: 20120244690Abstract: 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: ApplicationFiled: March 23, 2011Publication date: September 27, 2012Applicant: TOSHIBA AMERICA ELECTRONIC COMPONENTS, INC.Inventor: Yoshihiro Uozumi
-
Publication number: 20120245658Abstract: 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: ApplicationFiled: November 11, 2010Publication date: September 27, 2012Applicant: Merck Patent GmbHInventors: Junyou Pan, Herwig Buchholz, Ewald Aydt
-
Publication number: 20120237874Abstract: 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: ApplicationFiled: May 31, 2012Publication date: September 20, 2012Applicant: FUJIFILM CORPORATIONInventors: Shuhei Yamaguchi, Akinori Shibuya
-
Patent number: 8252505Abstract: 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: GrantFiled: February 16, 2009Date of Patent: August 28, 2012Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Akiya Kawaue, Keita Ishiduka, Kensuke Matsuzawa, Yoshiyuki Utsumi, Hiroaki Shimizu
-
Patent number: 8247160Abstract: 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: GrantFiled: July 13, 2009Date of Patent: August 21, 2012Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Yoshiyuki Utsumi, Keita Ishiduka, Kensuke Matsuzawa, Akiya Kawaue, Hiroaki Shimizu, Tsuyoshi Nakamura
-
Patent number: 8241831Abstract: 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: GrantFiled: September 5, 2008Date of Patent: August 14, 2012Assignee: Korea Kumho Petrochemical Co., Ltd.Inventors: Sung-Do Jung, Jin-Ho Kim, Jung-Hoon Oh, Hyun-Soon Lim
-
Patent number: 8227169Abstract: 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: GrantFiled: April 4, 2008Date of Patent: July 24, 2012Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Akiya Kawaue, Yoshiyuki Utsumi, Takehito Seo, Hideo Hada, Kotaro Endo, Daisuke Kawana, Yasuhiro Yoshii, Tsuyoshi Kurosawa
-
Publication number: 20120172606Abstract: 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: ApplicationFiled: December 30, 2011Publication date: July 5, 2012Applicant: Korea Kumho Petrochemical Co., Ltd.Inventors: Hyun Sang JOO, Dong Chul Seo, Dae Kyung Yoon, Dae Hyeon Shin
-
Publication number: 20120164582Abstract: 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: ApplicationFiled: March 8, 2012Publication date: June 28, 2012Applicant: JSR CorporationInventor: Ken MARUYAMA
-
Publication number: 20120141939Abstract: 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: ApplicationFiled: November 30, 2011Publication date: June 7, 2012Inventors: James W. Thackeray, Suzanne M. Coley, James F. Cameron, Paul J. LaBeaume, Ahmad E. Madkour, Owendi Ongayi, Vipul Jain
-
Publication number: 20120107210Abstract: 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: ApplicationFiled: November 28, 2011Publication date: May 3, 2012Applicant: Simbol Mining Corp.Inventors: Stephen Harrison, Robert Blanchet
-
Publication number: 20120100056Abstract: 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: ApplicationFiled: November 28, 2011Publication date: April 26, 2012Applicant: Simbol Mining Corp.Inventors: Stephen Harrison, Robert Blanchet
-
Patent number: 8163461Abstract: 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: GrantFiled: April 9, 2009Date of Patent: April 24, 2012Assignee: Cornell Research Foundation, Inc.Inventors: Christopher K. Ober, Yi Yi
-
Patent number: 8148044Abstract: 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: GrantFiled: October 29, 2009Date of Patent: April 3, 2012Assignee: Fujifilm CorporationInventors: Shuhei Yamaguchi, Tomotaka Tsuchimura, Yuko Tada
-
Publication number: 20120065425Abstract: 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: ApplicationFiled: September 10, 2010Publication date: March 15, 2012Applicant: E. I. DU PONT DE NEMOURS AND COMPANYInventors: ALLEN CAPRON SIEVERT, LEE GRANT SPRAGUE, JAMES A. SCHULTZ, KATELYN RAE WALCK
-
Patent number: 8114570Abstract: 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: GrantFiled: March 24, 2009Date of Patent: February 14, 2012Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Youichi Ohsawa, Takeshi Kinsho, Takeru Watanabe, Koji Hasegawa, Masaki Ohashi
-
Patent number: 8105748Abstract: 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: GrantFiled: October 16, 2009Date of Patent: January 31, 2012Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Masaki Ohashi, Youichi Ohsawa, Takeshi Kinsho, Jun Hatakeyama, Seiichiro Tachibana
-
Patent number: 8057985Abstract: 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: GrantFiled: August 27, 2009Date of Patent: November 15, 2011Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Masaki Ohashi, Takeshi Kinsho, Youichi Ohsawa, Jun Hatakeyama, Seiichiro Tachibana
-
Publication number: 20110269989Abstract: 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: ApplicationFiled: March 2, 2011Publication date: November 3, 2011Applicant: H R D CorporationInventors: Abbas HASSAN, Krishnan Viswanathan, Rayford G. Anthony, Gregory Borsinger, Aziz Hassan
-
Publication number: 20110269990Abstract: 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: ApplicationFiled: January 5, 2010Publication date: November 3, 2011Applicants: Mitsubishi Materials Electronic Chemicals Co., Ltd, MITSUBISHI MATERIALS CORPORATIONInventors: Tsunetoshi Honda, Hiroyuki Yatsuyanagi
-
Patent number: 8026391Abstract: 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: GrantFiled: September 29, 2006Date of Patent: September 27, 2011Assignees: Mitsubishi Materials Corporation, Mitsubishi Materials Electronic Chemicals Co., Ltd.Inventors: Masakazu Uotani, Hiroyuki Yatsuyanagi, Tsunetoshi Honda
-
Publication number: 20110215274Abstract: 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: ApplicationFiled: January 14, 2011Publication date: September 8, 2011Inventors: Cory Pecinovsky, William Thurmes, Brion C. Koprowski
-
Publication number: 20110200508Abstract: 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: ApplicationFiled: February 17, 2011Publication date: August 18, 2011Applicant: Simbol Mining Corp.Inventors: Stephen Harrison, Robert Blanchet
-
Publication number: 20110152540Abstract: 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: ApplicationFiled: August 4, 2008Publication date: June 23, 2011Inventors: Tesuyuki Nakayashiki, Kentaro Kimura
-
Publication number: 20110152537Abstract: 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: ApplicationFiled: May 12, 2009Publication date: June 23, 2011Applicant: MERCK PATENT GESELLSCHAFT MIT BESCHRANKTER HAFTUNGInventors: Peter Wasserscheid, Natalia Paape, Andreas Boesmann, Peter Schulz
-
Patent number: 7919226Abstract: 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: GrantFiled: August 13, 2008Date of Patent: April 5, 2011Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Youichi Ohsawa, Takeru Watanabe, Takeshi Kinsho, Katsuhiro Kobayashi
-
Patent number: 7901867Abstract: 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 acType: GrantFiled: June 21, 2006Date of Patent: March 8, 2011Assignee: BASF SEInventors: Jean-Pierre Wolf, Attila Latika, Jean-Luc Birbaum, Stephan Ilg, Pascal Hayoz
-
Patent number: 7901871Abstract: 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: GrantFiled: January 9, 2008Date of Patent: March 8, 2011Assignee: Samsung Electronics Co., Ltd.Inventors: Sung-ouk Jung, Seung-ju Seo, Jae-chan Park
-
Patent number: 7897807Abstract: 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: GrantFiled: February 22, 2010Date of Patent: March 1, 2011Assignee: E. I. du Pont de Nemours and CompanyInventors: Mark Andrew Harmer, Christopher P. Junk, Zoe Schnepp
-
Publication number: 20110034724Abstract: 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: ApplicationFiled: November 25, 2008Publication date: February 10, 2011Applicant: Rhodia OperationsInventors: Vincent Schanen, Olivier Buisine, François Metz, Bernard Besson
-
Patent number: 7862980Abstract: 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: GrantFiled: July 30, 2007Date of Patent: January 4, 2011Assignee: Sumitomo Chemical Company, LimitedInventors: Yukako Harada, Isao Yoshida, Yoshiyuki Takata
-
Publication number: 20100324330Abstract: 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: ApplicationFiled: August 10, 2010Publication date: December 23, 2010Inventors: Yasushi Akiyama, Yusuke Takano, Kiyohisa Takahashi, Sung-Eun Hong, Tetsuo Okayasu
-
Patent number: 7745097Abstract: 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: GrantFiled: July 16, 2008Date of Patent: June 29, 2010Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Hideo Hada, Takeshi Iwai, Takehiro Seshimo, Akiya Kawaue, Keita Ishiduka
-
Publication number: 20100145093Abstract: 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: ApplicationFiled: February 22, 2010Publication date: June 10, 2010Applicant: E. I. DU PONT DE NEMOURS AND COMPANYInventors: Mark Andrew Harmer, Christopher P. Junk, Zoe Schnepp
-
Patent number: 7728166Abstract: 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: GrantFiled: November 18, 2004Date of Patent: June 1, 2010Assignee: Sasol Solvents Germany GmbHInventors: Peter Finmans, Detlef Hoell, Hans-Jurgen Vossler, Martina Rozek, Michael James Green, Rafael Roggenbuck
-
Patent number: 7683209Abstract: 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: GrantFiled: June 6, 2006Date of Patent: March 23, 2010Assignee: E.I. du Pont de Nemours and CompanyInventors: Mark Andrew Harmer, Christopher P. Junk, Zoe Schnepp
-
Patent number: 7611822Abstract: 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: GrantFiled: July 22, 2008Date of Patent: November 3, 2009Assignee: Sumitomo Chemical Company, LimitedInventor: Ichiki Takemoto
-
Publication number: 20090269673Abstract: 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: ApplicationFiled: July 8, 2009Publication date: October 29, 2009Inventors: Nikolai Ignatyev, Michael Schmidt, Udo Heider, Peter Sartori, Andry Kucheryna
-
Patent number: 7601480Abstract: 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: GrantFiled: December 20, 2006Date of Patent: October 13, 2009Assignee: AZ Electronic Materials USA Corp.Inventors: M. Dalil Rahman, Takanori Kudo
-
Patent number: 7579132Abstract: 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: GrantFiled: June 4, 2007Date of Patent: August 25, 2009Assignee: Sumitomo Chemical Company, LimitedInventors: Yukako Harada, Isao Yoshida, Satoshi Yamaguchi
-
Patent number: 7579499Abstract: 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: GrantFiled: March 22, 2007Date of Patent: August 25, 2009Assignee: E. I. du Pont de Nemours and CompanyInventors: Victor Filippovich Cherstkov, Nina Ivanova Delyagina, Viacheslav A. Petrov, Paul R. Resnick
-
Patent number: 7569326Abstract: 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: GrantFiled: October 25, 2007Date of Patent: August 4, 2009Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Youichi Ohsawa, Masaki Ohashi, Seiichiro Tachibana, Jun Hatakeyama, Takeru Watanabe
-
Publication number: 20090143613Abstract: 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: ApplicationFiled: September 29, 2006Publication date: June 4, 2009Applicant: Mitsubishi Materials CorporationInventors: Masakazu Uotani, Hiroyuki Yatsuyanagi, Tsunetoshi Honda
-
Publication number: 20090137840Abstract: 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: ApplicationFiled: November 20, 2008Publication date: May 28, 2009Applicant: E. I. Du Pont de Nemours and CompanyInventors: Christopher P. Junk, Vsevolod Rostovtsev, Allen Capron Sievert, Lee G. Sprague
-
Publication number: 20090131684Abstract: 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: ApplicationFiled: September 29, 2008Publication date: May 21, 2009Inventors: Yool Kang, Hak-won Kim, Weoun-ju Kim, Seong-woon Choi, Hyun-woo Kim, Hai-sub Na, Kyoung-taek Kim
-
Patent number: 7531689Abstract: 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: GrantFiled: March 22, 2007Date of Patent: May 12, 2009Assignee: E.I. du Pont de Nemours and CompanyInventors: Victor Filippovich Cherstkov, Nina Ivanova Delyagina, Richard E. Fernandez, Viacheslav A. Petrov, Weiming Qiu, Paul R. Resnick
-
Patent number: 7524609Abstract: 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: GrantFiled: March 9, 2007Date of Patent: April 28, 2009Assignee: FUJIFILM CorporationInventor: Kenji Wada