Sulfur Compound Containing Patents (Class 430/921)
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Patent number: 8017302Abstract: 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 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: September 13, 2011Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Youichi Ohsawa, Takeshi Kinsho, Takeru Watanabe
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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: 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: 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: 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
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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: 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: 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: 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: 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: 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: 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: 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: 7803513Abstract: A chemically amplified resist composition comprising: (A) a salt represented by the formula (I): wherein R21 represents a C1-C30 hydrocarbon group etc., Q1 and Q2 each independently represent a fluorine atom etc., and A+ represents at least one organic cation selected from a cation represented by the formula (Ia): wherein P1, P2 and P3 each independently represent a C1-C30 alkyl group etc., a cation represented by the formula (Ib): wherein P4 and P5 each independently represent a hydrogen atom etc., and a cation represented by the formula (Ic): wherein P10, P11, P12, P13, P14, P15, P16, P17, P18, P19, P20 and P21 each independently represent a hydrogen atom etc.Type: GrantFiled: March 19, 2008Date of Patent: September 28, 2010Assignee: Sumitomo Chemical Company, LimitedInventors: Satoshi Yamaguchi, Yoshiyuki Takata, Kaoru Araki
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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: 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: 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: 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: 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: 7771912Abstract: A positive resist composition comprises: (A) a resin of which solubility in an alkali developer increases under the action of an acid, (B) a compound capable of generating an acid upon irradiation with actinic rays or radiation, (C) a resin having at least one repeating unit selected from fluorine atom-containing repeating units represented by the following formulae (1-1), (1-2) and (1-3), the resin being stable to an acid and insoluble in an alkali developer, and (D) a solvent: wherein R1 represents a hydrogen atom or an alkyl group; R2 represents a fluoroalkyl group; R3 represents a hydrogen atom or a monovalent organic group; R4 to R7 each independently represents a hydrogen atom, a fluorine atom, an alkyl group, a fluoroalkyl group, an alkoxy group or a fluoroalkoxy group, provided that at least one of R4 to R7 represents a fluorine atom, and R4 and R5, or R6 and R7 may combine to form a ring; R8 represents a hydrogen atom, a fluorine atom or a monovalent organic group; Rf represents a fluorine atomType: GrantFiled: December 11, 2006Date of Patent: August 10, 2010Assignee: FUJIFILM CorporationInventors: Kei Yamamoto, Shinichi Kanna, Hiromi Kanda
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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: 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: 7749679Abstract: A photosensitive composition containing a compound having a specific structure, a pattern-forming method using the photosensitive composition, and a compound having a specific structure used in the photosensitive composition.Type: GrantFiled: December 21, 2006Date of Patent: July 6, 2010Assignee: FUJIFILM CorporationInventors: Kenji Wada, Kunihiko Kodama
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Patent number: 7749677Abstract: The negative resist composition of the present invention comprises a silsesguioxane resin (A) comprising a constituent unit (a1) represented by the following general formula (I) and a constituent unit (a2) represented by the following general formula (II), an acid generator component (B) which generates an acid upon exposure, and a crosslinking agent component (C): wherein R1 represents a linear or branched alkylene group having 1 to 5 carbon atoms, andType: GrantFiled: March 11, 2005Date of Patent: July 6, 2010Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventor: Tomoyuki Ando
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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: 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: 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: 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: 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: 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: 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: 7682770Abstract: A resist composition is provided that yields fine resolution, and improved levels of line edge roughness and depth of focus. This composition includes a resin component (A) that undergoes a change in alkali solubility under the action of acid, and an acid generator component (B) that generates acid on exposure, wherein the component (A) is a resin with a weight average molecular weight of no more than 8,000 containing structural units (a) derived from a (meth)acrylate ester, and the component (B) includes at least one sulfonium compound represented by a general formula (b-1) or a general formula (b-2) shown below.Type: GrantFiled: October 20, 2004Date of Patent: March 23, 2010Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Hideo Hada, Masaru Takeshita, Ryotaro Hayashi, Syogo Matsumaru, Taku Hirayama, Hiroaki Shimizu
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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: 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: 7678529Abstract: A multilayer resist process comprises forming in sequence an undercoat film, an intermediate film, and a photoresist film on a patternable substrate, and effecting etching in multiple stages. A silicon-containing film forming composition is useful in forming the intermediate film serving as an etching mask, comprising a silicon-containing polymer obtained through hydrolytic condensation of at least one Si—Si bond-containing silane compound having formula: R(6-m)Si2Xm wherein R is a monovalent hydrocarbon group, X is alkoxy, alkanoyloxy or halogen, and m is 3 to 6. The composition allows the overlying photoresist film to be patterned to a satisfactory profile and has a high etching selectivity relative to organic materials.Type: GrantFiled: November 8, 2006Date of Patent: March 16, 2010Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Tsutomu Ogihara, Takeshi Asano, Motoaki Iwabuchi, Takafumi Ueda
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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: 7670749Abstract: A method for the formation of a patterned resist layer on a substrate surface by patternwise irradiation with actinic radiation. The first step of the method is formation of a coating layer comprising a substituted triphenylene compound having a diameter of between 1 and 3 nm, a sensitizer which increases the sensitivity of the exposed layer to the actinic radiation used in a subsequent irradiation step and a cross-linker on the substrate surface. Subsequently the coating layer is irradiated patternwise, and unirradiated areas of the coating layer are removed. A resist material comprising a solution of: (i) as the principal resist material a triphenylene derivative having a diameter of from 1 to 3 rim, (ii) a sensitizer which increases the sensitivity of the resist material to actinic radiation, and (iii) a cross-linker capable of cross-linking molecules of the triphenyl derivative, the cross-linker optionally being constituted by a moiety attached to the triphenylene derivative.Type: GrantFiled: September 19, 2005Date of Patent: March 2, 2010Assignee: The University of BirminghamInventors: Richard Edward Palmer, Alex Robinson, Jon Andrew Preece