Sulfur In Heterocyclic Ring Patents (Class 430/922)
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Patent number: 8283106Abstract: Disclosed is a fluorinated sulfonic acid salt or fluorinated sulfonic acid group-containing compound having a structure represented by the following general formula (A). In the formula, n indicates an integer of 1 to 10; R indicates a substituted or unsubstituted C1-C20 linear, branched or cyclic alkyl group, a substituted or unsubstituted C1-C20 linear, branched or cyclic alkenyl group, a substituted or unsubstituted C6-C15 aryl group, or a C4-C15 heteroaryl group; and a indicates 1 or 0. A photoacid generator containing the above fluorinated sulfonic acid salt or fluorinated sulfonic acid group-containing compound shows high sensitivity to an ArF excimer laser or the like, presents no concerns about human body accumulation, can generate an acid (photoacid) of sufficiently high acidity, and exhibits high solubility in a resist solvent and good compatibility with a resist resin.Type: GrantFiled: October 31, 2008Date of Patent: October 9, 2012Assignee: Central Glass Company, LimitedInventors: Kazuhiko Maeda, Yoshimi Isono, Satoru Narizuka
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Patent number: 8278030Abstract: An object of the present invention is to provide a sulfonium salt that has sufficient photosensitivity by active energy rays, such as visible light, ultraviolet rays, electron beams, and X-rays. The present invention is a sulfonium salt represented by formula (1). It is noted that R1 is a group represented by formula (2); R2 and R3 each represent an aryl group having 6 to 30 carbon atoms, a heterocyclic hydrocarbon group having 4 to 30 carbon atoms, an alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, or an alkynyl group having 2 to 30 carbon atoms; X? represents a monovalent polyatomic anion; R4 to R6 each represent an alkyl group, or the like; k represents an integer of 0 to 4; m represents an integer of 0 to 3; n represents an integer of 0 to 4; and A represents a group represented by —S—, —O—, —SO—, —SO2—, or —CO—.Type: GrantFiled: April 27, 2009Date of Patent: October 2, 2012Assignee: San-Apro LimitedInventors: Issei Suzuki, Hideki Kimura
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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
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Patent number: 8257905Abstract: A method of fabricating a thin film transistor substrate and a negative photoresist composition used therein are provided, which can reduce pattern inferiority. The method of fabricating a thin film transistor substrate includes forming a conductive film composed of a conductive material on a substrate, forming an etch pattern composed of a negative photoresist composition on the conductive film, and forming a conductive pattern by etching the conductive film using the etch pattern as an etching mask, wherein the negative photoresist composition includes 10-50 parts by weight of novolak resin including a hydroxyl group that is soluble in an alkali developing solution, 0.5-10 parts by weight of a first photo acid generator represented by the following formula (1), 0.Type: GrantFiled: January 11, 2010Date of Patent: September 4, 2012Assignee: Samsung Electronics Co., Ltd.Inventors: Yeong-Beom Lee, Hi-Kuk Lee, Byung-Uk Kim, Hyoc-Min Youn, Ki-Hyuk Koo
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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
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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
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Patent number: 8206888Abstract: It is intended to provide a radiation-sensitive resin composition, which comprises a radiation-sensitive acid generator excellent in resolution performance, heat stability, and storage stability, suppresses fluctuations in line width and deterioration in pattern profile attributed to standing waves, and produces a resist pattern improved in nano edge roughness and LEF. The radiation-sensitive resin composition is characterized by (A) a radiation-sensitive acid generator comprising: a sulfonium salt compound typified by 2,4,6-trimethylphenyldiphenylsulfonium 2,4-difluorobenzenesulfonate, 2,4,6-trimethylphenyldiphenylsulfonium 4-trifluoromethylbenzenesulfonate, or the like; and a sulfonimide compound. It is preferred that the composition should further comprise (B) a resin typified by a 4-hydroxystyrene/4-t-butoxystyrene copolymer, a 4-hydroxystyrene/t-butyl (meth)acrylate, or the like.Type: GrantFiled: November 21, 2006Date of Patent: June 26, 2012Assignee: JSR CorporationInventors: Yuuji Yada, Tomoki Nagai
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Patent number: 8206891Abstract: A positive resist composition including: a base component (A) which includes a polymeric compound (A1) containing a structural unit (a0) represented by the general formula (a0-1) and a structural unit (a1) derived from an acrylate ester having an acid dissociable, dissolution inhibiting group; and an acid generator component (B) which includes an acid generator (B1) containing an anion moiety represented by the general formula (I): (in the formula (a0-1), R1 represents a hydrogen atom, a lower alkyl group of 1 to 5 carbon atoms or a halogenated lower alkyl group of 1 to 5 carbon atoms; R2 represents a bivalent linking group; and R3 represents a cyclic group containing —SO2— within the ring skeleton. In the formula (I), X represents a cyclic group of 3 to 30 carbon atoms, Q1 represents a bivalent linking group containing an oxygen atom; Y1 represents an alkylene group of 1 to 4 carbon atoms or a fluorinated alkylene group of 1 to 4 carbon atoms).Type: GrantFiled: October 5, 2009Date of Patent: June 26, 2012Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Takehiro Seshimo, Yoshiyuki Utsumi, Akiya Kawaue, Takahiro Dazai, Tomoyuki Hirano, Fumitake Kaneko, Kotaro Endo
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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: 8173353Abstract: The present invention provides a sulfonium compound represented by the formula (I): wherein Q1 and Q2 each independently represent a fluorine atom or a C1-C6 perfluoroalkyl group, R1 represents a C5-C42 organic group having a ?-ketoester structure and A+ represents an organic counter ion, and a chemically amplified photoresist composition comprising the above-mentioned sulfonium compound and a resin comprising a structural unit having an acid-labile group and being insoluble or poorly soluble in an aqueous alkali solution but becoming soluble in an aqueous alkali solution by the action of an acid.Type: GrantFiled: March 23, 2010Date of Patent: May 8, 2012Assignee: Sumitomo Chemical Company, LimitedInventors: Tatsuro Masuyama, Junji Shigematsu, Hanwoo Park
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Patent number: 8158326Abstract: A compound which generates a sulfonic acid having one or more —SO3H groups and one or more —SO2— bonds upon irradiation with an actinic ray or a radiation; a photosensitive composition containing the compound; and a method of pattern formation with the photosensitive composition.Type: GrantFiled: August 13, 2008Date of Patent: April 17, 2012Assignee: Fujifilm CorporationInventors: Kunihiko Kodama, Kenji Wada, Kaoru Iwato
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Patent number: 8124313Abstract: A compound represented by general formula (I); and a compound represented by general formula (b1-1). wherein Q1 represents a divalent linkage group or a single bond; Y1 represents an alkylene group which may have a substituent or a fluorinated alkylene group which may have a substituent; X represents a cyclic group of 3 to 30 carbon atoms which may have a substituent, and has an —SO2— bond in the structure thereof; M+ represents an alkali metal ion; and A+ represents an organic cation.Type: GrantFiled: January 22, 2010Date of Patent: February 28, 2012Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Takehiro Seshimo, Yoshiyuki Utsumi, Akiya Kawaue, Hideo Hada, Hiroaki Shimizu, Tsuyoshi Nakamura
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Patent number: 8084183Abstract: A positive resist composition for electron beam, X-ray or EUV includes (A) a compound represented by the following formula (I), and (B) a resin capable of decomposing by the action of an acid to increase solubility in an alkali developing solution, which includes a repeating unit represented by the following formula (II) and a repeating unit represented by the following formula (III):Type: GrantFiled: August 1, 2008Date of Patent: December 27, 2011Assignee: Fujifilm CorporationInventors: Katsuhiro Yamashita, Yasutomo Kawanishi
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Patent number: 8048613Abstract: An alkali development-type solder resist includes (A) a carboxyl group-containing photosensitive resin obtained by reacting (a) a compound having two or more cyclic ether or thioether groups in the molecule with (b) an unsaturated monocarboxylic acid, reacting the product with (c) a polybasic acid anhydride, reacting the resulting resin with (d) a compound having a cyclic ether group and an ethylenic unsaturated group in the molecule, and reacting the product additionally with (c) a polybasic acid anhydride, (B) an oxime ester-based photopolymerization initiator containing a specific oxime ester group, (C) a compound having two or more ethylenic unsaturated groups in the molecule, and (D) a thermosetting component, wherein the dry film obtained by applying the composition has an absorbance of 0.3 to 1.2 per 25 ?m of the film thickness at a wavelength of 350 to 375 nm.Type: GrantFiled: October 13, 2008Date of Patent: November 1, 2011Assignee: Taiyo Ink Mfg. Co., Ltd.Inventors: Nobuhito Itoh, Yoko Shibasaki, Kenji Kato, Masao Arima
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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: 8034533Abstract: Fluorine-free photoacid generators and photoresist compositions containing fluorine-free photoacid generators are enabled as alternatives to PFOS/PFAS photoacid generator-containing photoresists. The photoacid generators are characterized by the presence of a fluorine-free heteroaromatic sulfonate anionic component. The photoacid generators preferably contain an onium cationic component, more preferably a sulfonium cationic component. The photoresist compositions preferably contain an acid sensitive imaging polymer. The compositions are especially useful for forming material patterns using 193 nm (ArF) imaging radiation.Type: GrantFiled: January 16, 2008Date of Patent: October 11, 2011Assignee: International Business Machines CorporationInventors: Sen Liu, Pushkara R. Varanasi
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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: 8021819Abstract: A photosensitive composition, which comprises a compound represented by formula (I): wherein R1 to R13 each independently represents a hydrogen atom or a substituent, and at least one of R1 to R13 is a substituent containing an alcoholic hydroxyl group; Z represents a single bond or a divalent linking group; and X? represents a counter anion; and a pattern-forming method using the photosensitive composition.Type: GrantFiled: February 7, 2007Date of Patent: September 20, 2011Assignee: FUJIFILM CorporationInventor: Yasutomo Kawanishi
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Patent number: 7989136Abstract: A photoresist composition comprises about 0.5 to about 20 parts by weight of a photo-acid generator, about 10 to about 70 parts by weight of a novolac resin containing a hydroxyl group, about 1 to about 40 parts by weight of a cross-linker that comprises an alkoxymethylmelamine compound, and about 10 to about 150 parts by weight of a solvent.Type: GrantFiled: March 31, 2008Date of Patent: August 2, 2011Assignees: Samsung Electronics Co., Ltd., Dongjin Semichem Co., Ltd.Inventors: Jeong-Min Park, Doo-Hee Jung, Hi-Kuk Lee, Hyoc-Min Yoon, Ki-Hyuk Koo
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Patent number: 7935474Abstract: An acid-amplifier having an acetal group and a photoresist composition including the same, are disclosed. The acid-amplifier produces an acid (second acid) during a post-exposure-bake (PEB), which is induced by an acid (first acid) generated from a photo-acid generator (PAG) at the exposure process so that a line edge roughness (LER) of the photoresist pattern and photoresist energy sensitivity are improved. The acid-amplifier has a structure of following Formula 1. in Formula 1, R is C4˜C20 mono-cyclic or multi-cyclic saturated hydrocarbon, R1 is C1˜C10 linear hydrocarbon, C1˜C10 perfluoro compound or C5˜C20 aromatic compound, Ra and Rb are independently hydrogen atom or C1˜C4 saturated hydrocarbon and A is independently oxygen atom (O) or sulfur atom (S).Type: GrantFiled: July 17, 2008Date of Patent: May 3, 2011Assignee: Dongjin Semichem Co., Ltd.Inventors: Jung-Youl Lee, Min-Ja Yoo, Jeong-Sik Kim, Young-Bae Lim, Jae-Woo Lee, Jae-Hyun Kim
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Patent number: 7927780Abstract: A compound represented by formula (I); and a compound represented by formula (b1-1): wherein X represents —O—, —S—, —O—R3— or —S—R4—, wherein each of R3 and R4 independently represents an alkylene group of 1 to 5 carbon atoms; R2 represents an alkyl group of 1 to 6 carbon atoms, an alkoxy group of 1 to 6 carbon atoms, a halogenated alkyl group of 1 to 6 carbon atoms, a halogen atom, a hydroxyalkyl group of 1 to 6 carbon atoms, a hydroxyl group or a cyano group; a represents an integer of 0 to 2; Q1 represents an alkylene group of 1 to 12 carbon atoms or a single bond; Y1 represents an alkylene group of 1 to 4 carbon atoms or a fluorinated alkylene group; M+ represents an alkali metal ion; and A+ represents an organic cation.Type: GrantFiled: September 10, 2008Date of Patent: April 19, 2011Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Akiya Kawaue, Takeshi Iwai, Hideo Hada, Shinichi Hidesaka, Tsuyoshi Kurosawa, Natsuko Maruyama, Kensuke Matsuzawa, Takehiro Seshimo, Hiroaki Shimizu, Tsuyoshi Nakamura
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Patent number: 7867697Abstract: A positive photosensitive composition comprises: (A) 5 to 20 parts by weight of the total amount of at least one compound that generates an acid upon irradiation with an actinic ray; and (B) 100 parts by weight of the total amount of at least one fluorine atom-containing resin having a group that increases a solubility of the resin in an alkaline developer by the action of an acid.Type: GrantFiled: July 22, 2004Date of Patent: January 11, 2011Assignee: FUJIFILM CorporationInventor: Kunihiko Kodama
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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
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Patent number: 7858287Abstract: A photosensitive resin realizes formation of a pattern having a good shape, without introducing poor compatibility between an acid generator and a photoresist primary-component polymer having an acid-dissociable group, and a photosensitive composition containing the photosensitive resin. The photosensitive resin includes a repeating unit represented by formula (1): (wherein R1 represents a C2-C9 linear or branched divalent hydrocarbon group; each of R2 to R5 represents a hydrogen atom or a C1-C3 linear or branched hydrocarbon group; each of R6 and R7 represents an organic group, wherein R6 and R7 may together form a divalent organic group; and X?represents an anion); at least one of a repeating unit represented by formula (2): (wherein R8 represents a C2-C9 linear or branched hydrocarbon group) and a repeating unit represented by formula (3): a repeating unit represented by formula (4): optionally, a repeating unit represented by formula (5).Type: GrantFiled: November 30, 2007Date of Patent: December 28, 2010Assignees: Hyogo Prefecture, Toyo Gosei Co., LtdInventors: Takeo Watanabe, Hiroo Kinoshita, Shinichi Yusa, Tomotaka Yamanaka, Masamichi Hayakawa, Yosuke Osawa, Satoshi Ogi, Yoshitaka Komuro
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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: 7851130Abstract: A photosensitive composition includes (A) a compound represented by the following formula (I): wherein R1 to R13 each independently represents a hydrogen atom or a substituent, Z represents a single bond or a divalent linking group, and X? represents an anion containing a proton acceptor functional group.Type: GrantFiled: September 19, 2007Date of Patent: December 14, 2010Assignee: FUJIFILM CorporationInventors: Yasutomo Kawanishi, Kenji Wada
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Patent number: 7816066Abstract: A positive resist composition includes a resin component (A), and an acid generator component (B) which generates an acid upon exposure and includes an acid generator (B1) represented by general formula (B1): (wherein R51 represents a straight chain, branched chain, or cyclic alkyl group, or a straight chain, branched chain, or cyclic fluorinated alkyl group; R52 represents a hydrogen atom, a hydroxyl group, a halogen atom, a straight chain, branched chain, or cyclic alkyl group, a straight chain or branched chain halogenated alkyl group, or a straight chain or branched chain alkoxy group; R53 represents an aryl group which may include a substituent; and n represents an integer from 1 to 3).Type: GrantFiled: April 7, 2006Date of Patent: October 19, 2010Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventor: Yohei Kinoshita
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Patent number: 7807329Abstract: A photosensitive composition comprises (A) a specific compound, which is excellent in sensitivity, resolution, and defocus latitude (DOF), and a pattern-forming method using the photosensitive composition is provided.Type: GrantFiled: March 13, 2006Date of Patent: October 5, 2010Assignee: FUJIFILM CorporationInventors: Kazuyoshi Mizutani, Yasutomo Kawanishi
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Patent number: 7803512Abstract: A positive resist composition that includes a resin component (A) that exhibits increased alkali solubility under the action of acid, and an acid generator component (B) that generates acid on exposure to radiation, wherein the component (A) includes a structural unit (a1) represented by a general formula (a1-2) or (a1-4), a structural unit (a2) derived from an acrylate ester that contains a lactone-containing monocyclic or polycyclic group, and a structural unit (a3), which is different from the structural unit (a1) and the structural unit (a2), and is derived from an acrylate ester that contains an aliphatic cyclic group-containing non-acid-dissociable, dissolution-inhibiting group and contains no polar groups, and the component (B) includes an onium salt (B1) having an anion portion represented by a formula: R41—SO3?.Type: GrantFiled: December 13, 2005Date of Patent: September 28, 2010Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Yohei Kinoshita, Isao Hirano
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Patent number: 7799505Abstract: The invention is related to an arylsulfonium salt compound having a polycyclic hydrocarbon structure in a cation moiety.Type: GrantFiled: October 23, 2007Date of Patent: September 21, 2010Assignee: FUJIFILM CorporationInventors: Kunihiko Kodama, Tomotaka Tsuchimura, Hiroshi Saegusa, Hideaki Tsubaki
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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: 7776510Abstract: A compound represented by general formula (b-14); and acid generator consisting of the compound; and a resist composition including a base component (A) which exhibits changed solubility in an alkali developing solution under action of acid and an acid-generator component (B) which generates acid upon exposure, the acid-generator component (B) including an acid generator (B1) consisting of a compound represented by general formula (b1-14): wherein R7? to R9? each independently represents an aryl group or an alkyl group, wherein two of R7? to R9? may be bonded to each other to form a ring with the sulfur atom, and at least one of R7? to R9? represents a substituted aryl group in which a portion or all of the hydrogen atoms are substituted with an alkoxyalkyloxy group or an alkoxycarbonylalkyloxy group; and X? represents an anion.Type: GrantFiled: June 9, 2008Date of Patent: August 17, 2010Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Takeshi Iwai, Hideo Hada, Keita Ishiduka, Akiya Kawaue, Hiroaki Shimizu, Kyoko Ohshita, Tsuyoshi Nakamura, Komei Hirahara, Yuichi Suzuki, Takehiro Seshimo
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Patent number: 7759045Abstract: A chemically amplified positive resist composition comprising (A) a salt represented by the formula (I): A+?O3S—R??(I) wherein R represents a 9,10-anthraquinonyl group which may be substituted with at least one group selected from the group consisting of a C1-C4 alkyl group, a C1-C4 alkoxy group and a hydroxyl group, and the C1-C4 alkyl group and the C1-C4 alkoxy group may be substituted, and A+ represents an organic counter cation, and (B) a resin which contains a structural unit which has an acid-labile group and which itself is insoluble or poorly soluble in an aqueous alkali solution but becomes soluble in an aqueous alkali solution by the action of an acid.Type: GrantFiled: June 24, 2008Date of Patent: July 20, 2010Assignee: Sumitomo Chemical Company, LimitedInventors: Makoto Akita, Isao Yoshida, Yukako Harada
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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
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Patent number: 7741015Abstract: A pattern is formed by applying a positive resist composition comprising a polymer comprising 7-oxanorbornane ring-bearing recurring units and acid labile group-bearing recurring units and an acid generator onto a substrate to form a resist film, heat treating and exposing the resist film to radiation, heat treating and developing the resist film with a developer, and causing the resist film to crosslink and cure with the aid of acid and/or heat. A second resist pattern is then formed in the space area of the first resist pattern. The double patterning process reduces the pitch between patterns to one half.Type: GrantFiled: February 12, 2008Date of Patent: June 22, 2010Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Jun Hatakeyama, Takao Yoshihara, Takeshi Kinsho, Koji Hasegawa, Yoshio Kawai, Katsuya Takemura
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Patent number: 7741007Abstract: The present invention provides a chemically amplified resist composition comprising: (A) a salt represented by the formula (1) wherein R21, Q1, Q2, and A+ defined in the specification; (B) a salt represented by the formula (II): wherein R22, Q3, Q4, and A?+ are defined in the specification; and (C) a resin which contains a structural unit having a structural unit having an acid-labile group and which itself is insoluble or poorly soluble in an aqueous alkali solution but becomes soluble in an aqueous alkali solution by the action of an acid.Type: GrantFiled: December 3, 2007Date of Patent: June 22, 2010Assignee: Sumitomo Chemical Company, LimitedInventors: Satoshi Yamaguchi, Satoshi Yamamoto, Nobuo 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: 7713679Abstract: There is provided a compound represented by a general formula (B1-1) shown below, an acid generator composed of the above compound, a resist composition containing an acid generator composed of the above compound, and a method of forming a resist pattern: (wherein RX represents a hydrocarbon group which may contain a substituent group; Q1 represents an alkylene group of 1 to 12 carbon atoms which may contain a substituent group, or a single bond; n represents an integer of 0 or 1; Y1 represents an alkylene group of 1 to 4 carbon atoms, or a fluorinated alkylene group of 1 to 4 carbon atoms; and A+ represents an organic cation which contains a nitrogen atom).Type: GrantFiled: October 14, 2008Date of Patent: May 11, 2010Inventors: Keita Ishiduka, Yoshiyuki Utsumi, Akiya Kawaue, Takehiro Seshimo, Hideo Hada
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Patent number: 7709179Abstract: A chemically amplified negative resist composition is provided in addition to a method of forming a resist pattern from which a desirable pattern shape can be obtained.Type: GrantFiled: April 7, 2006Date of Patent: May 4, 2010Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventor: Jun Iwashita
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Patent number: 7682772Abstract: A compound represented by general formula (I); and a compound represented by general formula (b1-1). [Chemical Formula 1] X-Q1-Y1—SO3?M+??(I) X-Q1-Y1—SO3?A+??(b1-1) wherein Q1 represents a divalent linkage group or a single bond; Y1 represents an alkylene group which may have a substituent or a fluorinated alkylene group which may have a substituent; X represents a cyclic group of 3 to 30 carbon atoms which may have a substituent, and has an —SO2— bond in the structure thereof; M+ represents an alkali metal ion; and A+ represents an organic cation.Type: GrantFiled: November 5, 2008Date of Patent: March 23, 2010Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Takehiro Seshimo, Yoshiyuki Utsumi, Akiya Kawaue, Hideo Hada, Hiroaki Shimizu, Tsuyoshi Nakamura
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Patent number: 7674567Abstract: A positive resist composition comprising: at least one compound selected from a compound capable of generating an acid represented by the formula (I) as defined herein upon irradiation with actinic rays or radiation and a compound capable of generating an acid represented by the following formula (II) upon irradiation with actinic rays or radiation; and a compound capable of generating an acid represented by the formula (III) as defined herein upon irradiation with actinic rays or radiation.Type: GrantFiled: September 20, 2006Date of Patent: March 9, 2010Assignee: FUJIFILM CorporationInventors: Kei Yamamoto, Shinichi Kanna
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Patent number: 7670746Abstract: A positive photosensitive composition comprises: (A) 5 to 20 parts by weight of the total amount of at least one compound that generates an acid upon irradiation with an actinic ray; and (B) 100 parts by weight of the total amount of at least one fluorine atom-containing resin having a group that increases a solubility of the resin in an alkaline developer by the action of an acid.Type: GrantFiled: July 22, 2004Date of Patent: March 2, 2010Assignee: FUJIFILM CorporationInventor: Kunihiko Kodama
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Patent number: 7618765Abstract: 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 which is a specific sulfonium salt compound. The resin (A) is a polymer comprising tertiary alkyl protective group units having a hydrophobic tetracyclo[4.4.0.12,5.17,10]dodecane structure, di- or trihydroxyadamantyl units, and monocyclic lactone units.Type: GrantFiled: January 2, 2008Date of Patent: November 17, 2009Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Tsunehiro Nishi, Seiichiro Tachibana, Katsuhiro Kobayashi
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Patent number: 7615323Abstract: Lithographic printing plate precursor comprising (a) a lithographic substrate with a hydrophilic surface and (b) a radiation-sensitive coating on the hydrophilic surface comprising (i) one or more types of monomers and/or oligomers and/or polymers, each comprising at least one ethylenically unsaturated group accessible to a free radical polymerization, (ii) at least one sensitizer, and at least one coinitiator capable of forming free radicals together with the sensitizer (ii); characterized in that the at least one sensitizer is an oligomeric or polymeric compound comprising the following structural unit (Formula (I)), wherein ?1 is an aromatic or heteroaromatic unit or a combination of the two so that a conjugated n-system is present between the two groups Z in structure (I), each Z independently represents a heteroatom, each R1 and R2 is independently selected from a halogen atom, an alkyl, aryl, alkylaryl or aralkyl group, a group —NR3R4 and a group —OR5, each R3, R4 and R5 is independently selected from aType: GrantFiled: November 11, 2005Date of Patent: November 10, 2009Assignee: Kodak Graphic Communications, GmbHInventors: Bernd Strehmel, Harald Baumann, Udo Dwars, Detlef Pietsch, Axel Draber, Michael Mursal
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Patent number: 7615330Abstract: A positive resist composition containing a compound including a sulfonium cation having a structure represented by the formula (Z-I) as defined herein, a low molecular weight compound which increases solubility in an alkali developing solution by an action of an acid, and a compound which generates a compound having a structure represented by the formula (A-I) as defined herein upon irradiation of an actinic ray or a radiation.Type: GrantFiled: March 26, 2007Date of Patent: November 10, 2009Assignee: FUJIFILM CorporationInventors: Sou Kamimura, Tomoya Sasaki, Yasutomo Kawanishi, Kenji Wada
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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
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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
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Patent number: 7575850Abstract: The present invention provides a chemically amplified resist composition comprising: a resin which comprises a structural unit having an acid-labile group and a structural unit represented by the formula (I): wherein R1 represents a hydrogen atom or a methyl group, ring X represents a C3-C30 cyclic hydrocarbon group in which one —CH2— is substituted with —COO—, and at least one hydrogen atom in the C3-C30 cyclic hydrocarbon group may be substituted, and p represents an integer of 1 to 4, and which itself is insoluble or poorly soluble in an alkali aqueous solution but becomes soluble in an alkali aqueous solution by the action of an acid, and at least two salts selected from a salt represented by the formula (II): wherein Y1 and Y2 each independently represent a fluorine atom or a C1-C6 perfluoroalkyl group, A+ represents an organic counter ion and R21 represents a C1-C30 hydrocarbon group which may be substituted and at least one —CH2— in the C1-C30 hydrocarbon group may be substituted with —COType: GrantFiled: January 28, 2008Date of Patent: August 18, 2009Assignee: Sumitomo Chemical Company, LimitedInventors: Yoshiyuki Takata, Satoshi Yamamoto, Satoshi Yamaguchi
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Patent number: 7572570Abstract: The present invention provides a chemically amplified resist composition comprising: (A) a resin which comprises (a) a structural unit having an acid-labile group, (b) a structural unit having at least one hydroxyl group, (c) a structural unit having at least one lactone structure, and (d) a structural unit represented by the formula (Ia) or (Ib): wherein R1 represents a hydrogen atom or a methyl group, R3 represents a methyl group, n represents an integer of 0 to 14, and Z represents a single bond or —[CH2]k—COO—, and (B) at least one acid generator.Type: GrantFiled: March 20, 2008Date of Patent: August 11, 2009Assignee: Sumitomo Chemical Company, LimitedInventors: Yusuke Fuji, Yoshiyuki Takata
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Patent number: 7566522Abstract: The present invention provides a chemically amplified resist composition comprising a resin which comprises a structural unit having an acid-labile group and a structural unit represented by the formula (I): wherein R1 represents a hydrogen atom or a methyl group, ring X represents a C3-C30 cyclic hydrocarbon group in which one —CH2— is substituted with —COO—, and at least one hydrogen atom in the C3-C30 cyclic hydrocarbon group may be substituted, and p represents an integer of 1 to 4, and which itself is insoluble or poorly soluble in an alkali aqueous solution but becomes soluble in an alkali aqueous solution by the action of an acid, and a salt represented by the formula (II): wherein Y1 and Y2 each independently represent a fluorine atom or a C1-C6 perfluoroalkyl group, A+ represents an organic counter ion, and R21 represents a C1-C30 hydrocarbon group which may be substituted and at least one —CH2— in the C1-C30 hydrocarbon group may be substituted with —CO— or —O—.Type: GrantFiled: December 11, 2007Date of Patent: July 28, 2009Assignee: Sumitomo Chemical Company, LimitedInventors: Yoshiyuki Takata, Takayuki Miyagawa, Kunishige Edamatsu