Halogen Compound Containing Patents (Class 430/925)
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Patent number: 8206886Abstract: A photosensitive composition comprises (A) a sulfonium or iodonium salt having an anion represented by one of formulae (I) and (II): wherein Y represents an alkylene group substituted with at least one fluorine atom, and R represents an alkyl group or a cycloalkyl group.Type: GrantFiled: January 25, 2005Date of Patent: June 26, 2012Assignee: FUJIFILM CorporationInventor: Kunihiko Kodama
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Patent number: 8173350Abstract: An oxime compound represented by the formula (I): wherein Y represents an unsubstituted or substituted n-valent C6-C14 aromatic hydrocarbon group, n represents an integer of 1 to 6, R1 represents a C1-C30 aliphatic hydrocarbon group etc., R2 represents a linear or branched chain C1-C20 aliphatic hydrocarbon group etc., W represents —CO—O— etc., Q1 and Q2 each independently represent a fluorine atom etc., Z represents a C1-C20 halogenated aliphatic hydrocarbon group etc, and the resist composition containing the same.Type: GrantFiled: July 21, 2009Date of Patent: May 8, 2012Assignee: Sumitomo Chemical Company, LimitedInventors: Tatsuro Masuyama, Kazuhiko Hashimoto, Takashi Hiraoka, Ichiki Takemoto
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Patent number: 8163463Abstract: A photoresist composition including an oxetane-containing compound represented by Formula 1 or 2, an oxirane-containing compound represented by Formula 3 or 4, a photoinitiator, and a solvent, a method of forming a pattern using the photoresist composition, and an inkjet print head including a polymerization product of the photoresist composition. The photoresist composition provides a polymerization product which resists formation of cracks due to an inner stress, and has excellent heat tolerance, excellent chemical resistance, excellent adhesiveness, and excellent durability.Type: GrantFiled: February 29, 2008Date of Patent: April 24, 2012Assignee: Samsung Electronics Co., Ltd.Inventors: Jin-baek Kim, Byung-ha Park, Kyu-sik Kim, Young-ung Ha, Su-min Kim
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Patent number: 8158329Abstract: The present invention provides a compound represented by the formula (I): wherein P1, P2, P3, P4 and P5 each independently represents a hydrogen atom etc., and at least one selected from the group consisting of R1, R2, R3, R4, R5, R6, R7, R8 and R9 is the group represented by the formula (II): wherein X1 and X2 each independently represent a hydrogen atom etc., n represents an integer of 1 to 4, Z1 represents a C1-C6 alkyl group etc., and ring Y represents an alicyclic hydrocarbon group, and the others each independently represent a hydrogen atom, a C1-C6 alkyl group or a hydroxyl group, and a chemically amplified resist composition containing the same.Type: GrantFiled: December 4, 2009Date of Patent: April 17, 2012Assignee: Sumitomo Chemical Company, LimitedInventors: Ichiki Takemoto, Nobuo Ando
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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
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Patent number: 8133653Abstract: A positive resist composition for forming a thick-film resist having a film thickness of 1 to 15 ?m, the composition comprising: a resin component (A) that includes a polymer compound (A1), which has a weight average molecular weight of 20,000 to 50,000, and includes a structural unit (a1) derived from a hydroxystyrene and a structural unit (a2) derived from an acrylate ester containing an acid dissociable, dissolution inhibiting group, an acid generator component (B) that generates acid upon exposure and includes an onium salt-based acid generator having an anion moiety represented by general formula (I): R4?SO3? (wherein, R4? represents a linear or branched alkyl group or fluoroalkyl group of 4 carbon atoms), and a nitrogen-containing organic compound (D) that includes a tertiary aliphatic amine.Type: GrantFiled: January 31, 2007Date of Patent: March 13, 2012Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Hiroshi Shimbori, Masahiro Masujima, Toshihiro Yamaguchi, Sachiko Yoshizawa
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Patent number: 8110337Abstract: A polymerizable composition containing: (A) a binder polymer; (B) a compound having a polymerizable unsaturated group; and (C) a compound which has a triarylsulfonium salt structure and in which a sum of Hammett's a constants of all substituents bonded to the aryl skeleton is larger than 0.46.Type: GrantFiled: December 18, 2003Date of Patent: February 7, 2012Assignee: Fujifilm CorporationInventor: Kazuto Shimada
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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
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Patent number: 8043786Abstract: The invention provides novel acid generators which are unproblematic in combustibility and accumulation inside the human body and can generate acids having high acidities and high boiling points and exhibiting properly short diffusion lengths in resist coating films and which permit the formation of resist patterns excellent smoothness with little dependence on the denseness of a mask pattern; sulfonic acids generated from the acid generators; sulfonyl halides useful as raw material in the synthesis of the acid generators; and radiation-sensitive resin compositions containing the acid generators. The acid generators have structures represented by the general formula (I), wherein R1 is a monovalent substituent such as alkoxycarbonyl, alkylsulfonyl, or alkoxysulfonyl; R2 to R4 are each hydrogen or alkyl; k is an integer of 0 or above; and n is an integer of 0 to 5.Type: GrantFiled: February 20, 2004Date of Patent: October 25, 2011Assignee: JSR CorporationInventors: Satoshi Ebata, Yong Wang, Isao Nishimura
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Patent number: 8039200Abstract: A photosensitive composition comprises (A) a sulfonium or iodonium salt having an anion represented by one of formulae (I) and (II): wherein Y represents an alkylene group substituted with at least one fluorine atom, and R represents an alkyl group or a cycloalkyl group.Type: GrantFiled: August 10, 2010Date of Patent: October 18, 2011Assignee: FUJIFILM CorporationInventor: Kunihiko Kodama
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Patent number: 8034546Abstract: The use as a resist material of a methanofullerene derivative having a plurality of open-ended addends, and to a method for forming a patterned resist layer on a substrate using the methanofullerene derivatives. The methanofullerene derivatives can be represented by the formal C2x(CR1R2)m where x is at least 10, m is at least 2, each addend represented by CR1R2 is the same or different, and wherein each R1 and R2 is each a monovalent organic group, or a divalent organic group which forms a ring structure by being joined to the fullerene shell, or where both R1 and R2 of an addend are divalent groups, they may be mutually joined to form a ring structure, save that at least two of R1 or two of R2 are monovalent, or a mixture of such derivatives. The use of any methanofullerene derivative which has been chemically amplified for formation of a patterned resist layer.Type: GrantFiled: September 19, 2005Date of Patent: October 11, 2011Assignee: The University of BirminghamInventors: Alex Robinson, Jon Andrew Preece, Richard Edward Palmer
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Patent number: 8029971Abstract: Compositions, a method, and a photopatternable blend. The compositions include a blend of a first and a second polymer. The first polymer is a substituted silsesquioxane copolymer. The second polymer is a substituted silsesquioxane polymer. The second polymer is configured to undergo chemical crosslinking with the first polymer, the second polymer, or a combination thereof, upon exposure to light, thermal energy, or a combination thereof. The compositions include a photosensitive acid generator. The method includes forming a film. The film is patternwise imaged, and at least one region is exposed to radiation. After the imaging, the film is baked, wherein at least one exposed region is rendered substantially soluble. After the baking, the film is developed, wherein a relief pattern remains. The relief pattern is exposed to radiation. The relief pattern is baked. The relief pattern is cured. A chemically amplified positive-tone photopatternable blend is also described.Type: GrantFiled: March 13, 2008Date of Patent: October 4, 2011Assignee: International Business Machines CorporationInventors: Robert D. Allen, Phillip Joe Brock, Blake W. Davis, Qinghuang Lin, Robert D. Miller, Alshakim Nelson, Ratnam Sooriyakumaran
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Patent number: 8029975Abstract: A resist composition and a method for forming a patterned feature on a substrate. The composition comprises a molecular glass having at least one fused polycyclic moiety and at least one base soluble functional group protected with an acid labile protecting group, and a photosensitive acid generator. The method includes providing a composition including a photosensitive acid generator and a molecular glass having at least one fused polycyclic moiety and at least one base soluble functional group protected with an acid labile protecting group, forming a film of the composition on the substrate, patternwise imaging the film, wherein at least one region of the film is exposed to radiation or a beam of particles, resulting in production of an acid catalyst in the exposed region, baking the film, developing the film, resulting in removal of base-soluble exposed regions, wherein a patterned feature from the film remains following the removal.Type: GrantFiled: July 24, 2009Date of Patent: October 4, 2011Assignee: International Business Machines CorporationInventors: James J. Bucchignano, Wu-Song Huang, Pushkara R. Varanasi, Roy R. Yu
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Patent number: 8021823Abstract: There is provided a positive resist composition, including a base component (A) which exhibits increased solubility in an alkali developing solution under action of an acid, and an acid generator component (B) which generates an acid upon exposure, wherein the base component (A) includes a polymeric compound (A1) containing a structural unit (a0) represented by the general formula (a0-1) shown below: (wherein, R1 represents a hydrogen atom, a lower alkyl group or a halogenated lower alkyl group; A represents a bivalent linking group; B represents a bivalent linking group; and R2 represents an acid dissociable, dissolution inhibiting group).Type: GrantFiled: February 18, 2009Date of Patent: September 20, 2011Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Hiroaki Shimizu, Tsuyoshi Nakamura, Takahiro Dazai, Daiju Shiono, Tomoyuki Hirano
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Patent number: 8003294Abstract: A photosensitive composition comprises: (A) a compound capable of generating an acid represented by formula (I) upon irradiation with actinic ray or radiation; and (B) a resin that decomposes by the action of an acid to its increase solubility in an alkali developer wherein Ra represents an alkyl group substituted with a fluorine atom, or an aryl group substituted with a fluorine atom or a group having a fluorine atom; Rb represents an alkyl group not substituted with a fluorine atom on ?-position of the alkyl group, or an aryl group not substituted with a fluorine atom or a group having a fluorine atom.Type: GrantFiled: March 10, 2008Date of Patent: August 23, 2011Assignee: FUJIFILM CorporationInventor: Kunihiko Kodama
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Patent number: 7993811Abstract: A positive resist composition comprises (A) a resin component which becomes soluble in an alkaline developer under the action of an acid and (B) an acid generator. The resin (A) is a polymer comprising specific recurring units, represented by formula (1). The acid generator (B) is a specific sulfonium salt compound. When processed by lithography, the composition is improved in resolution and forms a pattern with a satisfactory mask fidelity and a minimal LER. Herein R1 is H or methyl, R2 is an acid labile group, R3 is CO2R4 when X is CH2, R3 is H or CO2R4 when X is O, R4 is a monovalent C1-C20 hydrocarbon group, and m is 1 or 2.Type: GrantFiled: January 16, 2009Date of Patent: August 9, 2011Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Youichi Ohsawa, Takeshi Kinsho, Takeru Watanabe
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Patent number: 7977030Abstract: A photosensitive resin composition, a photosensitive resin laminate, and a method for forming a pattern capable of realizing high hardness while using an epoxy group-containing acrylic resin are provided. In a photosensitive resin composition including (A) an epoxy group-containing acrylic resin, (B) a photopolymerization initiator, and (C) a sensitizer, an onium salt having a specific structure is used as the component (B), and at least one kind selected from 1,5-dihydroxynaphthalene, 2,3-dihydroxynaphthalene, and 2,6-dihydroxynaphthalene is used as the component (C).Type: GrantFiled: June 10, 2008Date of Patent: July 12, 2011Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Takahiro Senzaki, Koichi Misumi, Koji Saito
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Patent number: 7919225Abstract: A method and a composition. The composition includes at least one carbosilane-substituted silsesquioxane polymer which crosslinks in the presence of an acid. The at least one carbosilane-substituted silsesquioxane polymer is soluble in aqueous base. The method includes forming a coating on a substrate. The coating includes one or more carbosilane-substituted silsesquioxane polymers. The carbosilane-substituted silsesquioxane polymer is soluble in aqueous base. The coating is exposed to radiation, resulting in generating a latent pattern in the coating. The exposed coating is baked at a first temperature less than about 150° C. The baked coating is developed, resulting in forming a latent image from the latent pattern in the baked coating. The latent image is cured at a second temperature less than about 500° C.Type: GrantFiled: May 23, 2008Date of Patent: April 5, 2011Assignee: International Business Machines CorporationInventors: Robert D. Allen, Phillip Joe Brock, Blake W. Davis, Geraud Jean-Michel Dubois, Qinghuang Lin, Robert D. Miller, Alshakim Nelson, Sampath Purushothaman, Ratnam Sooriyakumaran
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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
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Patent number: 7892719Abstract: Embodiments of the present invention provide EUV (extreme ultraviolet) photoresists comprising photonic crystals, as well as other components. Photonic crystals in general provide the ability not only to block light transmission, but also to create resonant pockets in which light can propagate. The photonic crystals are based on bio-related polymers that are capable of self-assembly into crystalline form.Type: GrantFiled: November 3, 2006Date of Patent: February 22, 2011Assignee: Intel CorporationInventor: Eric C. Hannah
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Patent number: 7883828Abstract: Linear or branched functionalized polycarbosilanes having an absorbance less than 3.0 ?m?1 at 193 nm and a relatively high refractive index are provided. The functionalized polycarbosilanes contain at least one pendant group that is acid labile or aqueous base soluble. Also disclosed are photoresists formulations containing the functionalized polycarbosilanes that are suitable for use in lithography, e.g., immersion lithography.Type: GrantFiled: March 28, 2008Date of Patent: February 8, 2011Assignee: International Business Machines CorporationInventors: Robert D. Allen, Matthew E. Colburn, Daniel P. Sanders, Ratnam Sooriyakumaran, Hoa D. Truong
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Patent number: 7871761Abstract: Provided is a method for forming a resist lower layer material for use in a multilayer resist process, especially two-layer resist process or three-layer resist process, having a function of neutralizing an amine contaminant from a substrate, thereby reducing a harmful effect such as trailing skirts of a resist pattern of an upper layer resist. Specifically, there is provided a material for forming a lower layer of a chemically amplified photoresist layer comprising a crosslinkable polymer and a thermal acid generator that can generate an acid by heating at 100° C. or greater and is represented by the general formula (1a): R1CF2SO3?(R2)4N+??(1a), as well as a resist lower layer substrate comprising a resist lower layer formed using said material.Type: GrantFiled: July 27, 2007Date of Patent: January 18, 2011Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Jun Hatakeyama, Toshihiko Fujii, Youichi Ohsawa
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Patent number: 7867689Abstract: A method. The method includes dip coating a film of a composition on a silicon wafer substrate. The composition includes a polymer blend of a first polymer and a second polymer. The first polymer is a substituted silsesquioxane copolymer. The second polymer is a polysilsesquioxane having silanol end groups. The composition includes a photosensitive acid generator, an organic base, and an organic crosslinking agent. The film is patternwise imaged and at least one region is exposed to radiation having a wavelength of about 248 nanometers. The film is baked, resulting in inducing crosslinking in the film. The film is developed resulting in removal of base-soluble unexposed regions of the film, wherein a relief pattern from the film remains. The relief pattern is cured at a temperature between about 300° C. and about 450° C., and the curing utilizes a combination of thermal treatment with UV radiation.Type: GrantFiled: May 18, 2007Date of Patent: January 11, 2011Assignee: International Business Machines CorporationInventors: Robert D. Allen, Phillip Brock, Blake W. Davis, Qinghuang Lin, Robert D. Miller, Alshakim Nelson, Ratnam Sooriyakumaran
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Patent number: 7858286Abstract: A positive resist composition and method for forming a resist pattern are provided which enable a resist pattern with excellent shape to be obtained.Type: GrantFiled: April 7, 2006Date of Patent: December 28, 2010Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Yohei Kinoshita, Makiko Irie, Waki Ohkubo, Yusuke Nakagawa, Shinichi Hidesaka
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Patent number: 7833690Abstract: The present invention relates to photoacid generating compounds, lithographic resists comprising photoacid generating compounds, and to various lithographic processes techniques, and applications.Type: GrantFiled: October 6, 2006Date of Patent: November 16, 2010Assignee: The University of North Carolina at CharlotteInventors: Kenneth E. Gonsalves, Mingxing Wang
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Patent number: 7812194Abstract: A positive photosensitive composition comprises a compound capable of generating a specified sulfonic acid upon irradiation with one of an actinic ray and radiation and (B) a resin capable of decomposing under the action of an acid to increase the solubility in an alkali developer.Type: GrantFiled: August 30, 2006Date of Patent: October 12, 2010Assignee: FUJIFILM CorporationInventors: Kunihiko Kodama, Toshiaki Aoai
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Patent number: 7803511Abstract: A positive resist composition for immersion exposure comprises: (A) a resin capable of increasing its solubility in an alkali developer by an action of an acid, and (B) a compound capable of generating an acid upon irradiation with actinic ray or radiation, wherein the acid satisfies conditions of V?230 and V/S?0.93 taking van der Waals volume of the acid as V (?3), and van der Waals surface area of the acid as S (?2).Type: GrantFiled: August 15, 2006Date of Patent: September 28, 2010Assignee: FUJIFILM CorporationInventors: Haruki Inabe, Hiromi Kanda, Kunihiko Kodama
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Patent number: 7794914Abstract: The present invention provides a chemically amplified resist composition comprising: a resin (A) which contains no fluorine atom and a structural unit (a1) having an acid-labile group, a resin (B) which contains a structural unit (b2) having a fluorine-containing group and at least one structural unit selected from a structural unit (b1) having an acid-labile group, a structural unit (b3) having a hydroxyl group and a structural unit (b4) having a lactone structure, and an acid generator.Type: GrantFiled: February 12, 2007Date of Patent: September 14, 2010Assignee: Sumitomo Chemical Company, LimitedInventors: Nobuo Ando, Yusuke Fuji, Ichiki Takemoto
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Patent number: 7781144Abstract: The present invention is a positive resist composition and a resist pattern forming method including a resin component (A) which has a polymer compound (A1) having a structural units (a1) including an acetal type acid dissociable, dissolution inhibiting group, a structural unit (a2) derived from an acrylate ester having a lactone-containing polycyclic group, and a structural unit (a3) derived from an acrylate ester having a polar group-containing aliphatic hydrocarbon group, and an acid generator component (B) having an onium salt-based acid generator (B1) having a cation portion represented by a general formula (b-1) shown below [wherein, R11 represents an alkyl group, an alkoxy group, a halogen atom or a hydroxyl group; R12 to R13 each represents, independently, an aryl group or the alkyl group that may have substituent group; n? represents either 0 or an integer from 1 to 3].Type: GrantFiled: April 18, 2006Date of Patent: August 24, 2010Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Yohei Kinoshita, Waki Ohkubo, Yusuke Nakagawa, Shinichi Hidesaka, Makiko Irie
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Patent number: 7776512Abstract: A positive photosensitive composition comprises a compound capable of generating a specified sulfonic acid upon irradiation with one of an actinic ray and radiation and (B) a resin capable of decomposing under the action of an acid to increase the solubility in an alkali developer.Type: GrantFiled: January 29, 2009Date of Patent: August 17, 2010Assignee: FUJIFILM CorporationInventors: Kunihiko Kodama, Toshiaki Aoai
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Patent number: 7776505Abstract: The present invention addresses many of the current limitations in sub-100 nm lithographic techniques by providing novel resists that achieve high sensitivity, high contrast, high resolution, and high dry-etch resistance for pattern transfer to a substrate. In one embodiment, the present invention provides a polymeric resist comprising an adamantyl component and a photoacid generating component.Type: GrantFiled: September 14, 2005Date of Patent: August 17, 2010Assignee: The University of North Carolina at CharlotteInventor: Kenneth E. Gonsalves
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Patent number: 7763412Abstract: A polymer, a positive resist composition, and a method for forming a resist pattern that are able to form a resist pattern with a high level of resolution and excellent etching resistance. The present invention uses a polymer that contains a structural unit (a1) represented by a general formula (a-1) shown below and a structural unit (a2) represented by a general formula (a-2) shown below, another polymer that contains the structural unit (a1) and a structural unit (a3) represented by a general formula (a-3) shown below, and another polymer that contains the structural unit (a1), the structural unit (a2), and the structural unit (a3).Type: GrantFiled: June 2, 2005Date of Patent: July 27, 2010Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Masaru Takeshita, Hideo Hada, Ryotaro Hayashi, Takeshi Iwai, Syogo Matsumaru, Satoshi Fujimura
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Patent number: 7749680Abstract: A photoresist composition includes a base resin, a copolymer of acrylic acid or methacrylic acid and 3,3-dimethoxypropene, a photoacid generator, an organic base, and an organic solvent, and is used for forming a fine (micro) pattern in a semiconductor device by double patterning. The invention method can markedly reduce the number of steps in etching and hard mask deposition processes, so that work hours and manufacturing costs may be reduced, contributing to an increase in yield of semiconductor devices.Type: GrantFiled: June 26, 2007Date of Patent: July 6, 2010Assignee: Hynix Semiconductor Inc.Inventors: Jae Chang Jung, Sung Koo Lee
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Patent number: 7745098Abstract: A polymer compound having a structural unit (a0) represented by a general formula (a0-1) shown below, and a structural unit (a1) that is derived from an acrylate ester containing an acid dissociable, dissolution inhibiting group but is not classified as said structural unit (a0).Type: GrantFiled: August 26, 2008Date of Patent: June 29, 2010Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Takahiro Dazai, Takayoshi Mori, Hiroaki Shimizu, Kyoko Ohshita, Komei Hirahara
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Patent number: 7741009Abstract: A positive resist composition including a resin component (A) which exhibits increased solubility in an alkali developing solution under action of acid and has a structural unit (a1) represented by general formula (a1-0-2) shown below, and an acid-generator component (B) which generates acid upon exposure and includes an acid generator (B1) consisting of a compound represented by general formula (b1-12) shown below: wherein R represents a hydrogen atom, a lower alkyl group or a halogenated lower alkyl group; X2 represents an acid dissociable, dissolution inhibiting group; and Y2 represents an alkylene group or a divalent aliphatic cyclic group; and R2—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 substituted with a fluorine atom; and A+ represents a cation.Type: GrantFiled: July 17, 2008Date of Patent: June 22, 2010Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Takahiro Dazai, Hiroaki Shimizu, Kyoko Ohshita, Komei Hirahara
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Patent number: 7736842Abstract: A resist composition for electron beam or extreme ultraviolet (EUV), comprising a resin component (A) which exhibits changed alkali solubility under action of acid, and a photoacid generator component (B) that generates acid on exposure, wherein the component (B) comprises at least one onium salt selected from the group consisting of onium salts having an anion represented by formula (b-0-1) or (b-0-2) shown below: wherein X represents an alkylene group having 2 to 6 carbon atoms, in which at least one hydrogen atom is substituted with a fluorine atom; and each of Y and Z independently represents an alkyl group having 1 to 10 atoms, in which at least one hydrogen atom is substituted with a fluorine atom.Type: GrantFiled: September 1, 2005Date of Patent: June 15, 2010Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Hideo Hada, Daiju Shiono, Hiroo Kinoshita, Takeo Watanabe
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Patent number: 7727704Abstract: In a positive resist composition comprising (A) a resin component which becomes soluble in an alkaline developer under the action of an acid and (B) a photoacid generator, component (A) is a polymer of formula (1) wherein R1 is H, methyl or trifluoromethyl, R2 and R3 are alkyl, R4 is a monovalent hydrocarbon group, X1 is O, S or CH2CH2, X2 is O, S, CH2 or CH2CH2, n is 1 or 2, a1, a2, c, d1 and d2 each are from 0 to less than 1, b is from 0.01 to less than 1, and a1+a2+b+c+d1+d2=1. The resist composition forms a pattern with high rectangularity at an enhanced resolution when processed by ArF lithography.Type: GrantFiled: July 5, 2007Date of Patent: June 1, 2010Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Ryosuke Taniguchi, Tsunehiro Nishi, Tomohiro Kobayashi
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Patent number: 7727701Abstract: A positive resist composition that exhibits a large exposure margin, and excellent levels of resolution and dry etching resistance, as well as a method of forming a resist pattern that uses the positive resist composition.Type: GrantFiled: January 14, 2005Date of Patent: June 1, 2010Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Takuma Hojo, Kiyoshi Ishikawa, Tomoyuki Ando
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Patent number: 7718344Abstract: A resist composition, includes: (B) a polymer having a group capable of decomposing under an action of an acid and having a weight average molecular weight of 1,000 to 5,000, of which solubility in an alkali developer increases under an action of an acid; and (Z) a compound containing a sulfonium cation having a structure represented by formula (Z-1): wherein Y1 to Y13 each independently represents a hydrogen atom or a substituent, and adjacent members of Y1 to Y13 may combine with each other to form a ring; and Z represents a single bond or a divalent linking group.Type: GrantFiled: September 28, 2007Date of Patent: May 18, 2010Assignee: FUJIFILM CorporationInventors: Sou Kamimura, Kenji Wada, Yasutomo Kawanishi
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Patent number: 7700264Abstract: A photosensitive resin composition containing an alkali soluble resin, an ethylenically unsaturated compound, a near infrared absorbing dye, a compound containing a halomethyl group and a compound containing an organoboron anion, wherein the alkali soluble resin is an acryl resin having one or more pendant groups in which both terminals of a diol compound have been blocked with isophorone diisocyanates and then (meth)acryloyl has been added. Also provided is an image forming material having a substrate, and a photosensitive layer formed by the photosensitive resin composition on the substrate, as well as an image forming method.Type: GrantFiled: October 31, 2006Date of Patent: April 20, 2010Assignee: Nippon Paint Co., Ltd.Inventor: Hirotoshi Umemoto
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Patent number: 7695891Abstract: A photosensitive composition comprising a compound capable of generating a compound having a specific structure upon irradiation with actinic rays or radiation; a pattern forming method using the photosensitive composition; a compound having a specific structure; and a compound capable of generating a compound having a specific structure upon irradiation with actinic rays or radiation.Type: GrantFiled: June 21, 2006Date of Patent: April 13, 2010Assignee: FUJIFILM CorporationInventor: Kenji Wada
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Patent number: 7678528Abstract: The present invention relates to novel photoacid generators.Type: GrantFiled: February 16, 2006Date of Patent: March 16, 2010Assignee: AZ Electronic Materials USA Corp.Inventors: M. Dalil Rahman, Munirathna Padmanaban
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Patent number: 7651830Abstract: Provided is an article that comprises a substrate comprising an acid-etchable layer, a water-soluble polymer matrix, and a photoacid generator. Also provided is a method for patterning that can provide patterned layers that can be used to form electroactive devices.Type: GrantFiled: June 1, 2007Date of Patent: January 26, 2010Assignee: 3M Innovative Properties CompanyInventors: Wayne S Mahoney, Steven D. Theiss
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Patent number: 7635554Abstract: A positive photosensitive composition comprises: (A) a resin that has an acid decomposable repeating unit represented by formula (I) and increases its solubility in an alkali developer by action of an acid: (B) a compound generating an acid upon irradiation with actinic light or radiation; (C) a hydrophobic resin insoluble in an alkali developer and having at least either one of a fluorine atom and a silicon atom; and (D) a solvent, wherein in the formula (I), Xa1 represents a hydrogen atom, an alkyl group, a cyano group or a halogen atom, Ry1 to Ry3 each independently represents an alkyl group or a cycloalkyl group, and at least two of Ry1 to Ry3 may be coupled to form a ring structure, and Z represents a divalent linking group.Type: GrantFiled: March 28, 2008Date of Patent: December 22, 2009Assignee: FUJIFILM CorporationInventors: Toshiaki Fukuhara, Shinichi Kanna, Hiromi Kanda
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Patent number: 7629106Abstract: There is disclosed a resist composition which shows high sensitivity and high resolution on exposure to high energy beam, provides reduced Line Edge Roughness because swelling at the time of development is reduced, provides minor amounts of residue after development, has excellent dry etching resistance, and can also be used suitably for the liquid immersion lithography; and a patterning process using the resist composition. There can be provided a resist composition which comprises, at least, a polymer including repeating units represented by the following general formulae (a) and (b).Type: GrantFiled: October 16, 2006Date of Patent: December 8, 2009Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Jun Hatakeyama, Koji Hasegawa, Youichi Ohsawa, Seiichiro Tachibana
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Patent number: 7625687Abstract: This invention pertains to a silsesquioxane resin with improved lithographic properties (such as etch-resistance, transparency, resolution, sensitivity, focus latitude, line edge roughness, and adhesion) suitable as a photoresist; a method for in-corporating the fluorinated or non-fluorinated functional groups onto silsesquioxane backbone. The silsesquioxane resins of this invention has the general structure (HSiO3/2)a(RSiO3/2)b wherein; R is an acid dissociable group, a has a value of 0.2 to 0.9 and b has a value of 0.1 to 0.8 and 0.9?a+b?1.0.Type: GrantFiled: June 30, 2004Date of Patent: December 1, 2009Assignee: Dow Corning CorporationInventors: Sanlin Hu, Eric Scott Moyer, Sheng Wang, David Lee Wyman
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Patent number: 7592128Abstract: The present invention relates to negative-working imageable elements that can be used for the manufacture of printing plates. These imageable elements can be developed on on-press by the action of a lithographic printing ink used in combination with either water or a fountain solution. The imageable elements comprise an imageable layer that is not removable in water or fountain solution alone. The imageable layer includes a free radically polymerizable compound, a free radical initiator composition, an infrared radiation absorbing compound, and a polymeric binder comprising poly(alkylene oxide) pendant groups, and preferably additionally pendant cyano groups.Type: GrantFiled: August 7, 2006Date of Patent: September 22, 2009Assignee: Eastman Kodak CompanyInventors: Jianbing Huang, Kevin B. Ray, Scott A. Beckley
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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
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Patent number: 7560219Abstract: Sulfonium salt photoinitiator compositions, precursors useful in the preparation of such photoinitiators and the use of these photoinitiators in, e.g., UV curable adhesives, UV curable sealants, UV curable coating compositions, such as printing inks and varnishes, and UV curable encapsulants.Type: GrantFiled: April 26, 2007Date of Patent: July 14, 2009Assignee: Henkel AG & Co. KGaAInventors: Yuxia Liu, Donald E. Herr
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Patent number: RE43560Abstract: A positive photosensitive composition comprising (A) a compound capable of generating a fluorine-substituted alkanesulfonic acid having 2 to 4 carbon atoms by irradiation of actinic rays or radiation, (B) a resin having a monocyclic or polycyclic alicyclic hydrocarbon structure and being decomposed by the action of an acid to increase solubility in an alkali developer, (C) a basic compound, and (D) a fluorine and/or silicon surfactant.Type: GrantFiled: December 30, 2009Date of Patent: July 31, 2012Assignee: FUJIFILM CorporationInventors: Kunihiko Kodama, Toshiaki Aoai