Polymer Of Unsaturated Acid Or Ester Patents (Class 430/910)
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Patent number: 8241831Abstract: An acid generating agent represented by the following formula (1) or (2) is provided, which is included in chemically amplified resist compositions: wherein in the formula (1) and (2), X represents an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms and selected from alkyl, haloalkyl and alkylsulfonyl, which may have at least one hydrogen atom substituted by an ether group, an ester group, a carbonyl group, an acetal group, a nitrile group, a cyano group, a hydroxyl group, a carboxyl group or an aldehyde group, or represents a perfluoroalkyl group having 1 to 4 carbon atoms; R6 represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or a heteroatom selected from nitrogen, sulfur, fluorine and oxygen; m is an integer from 0 to 2; and A+ is an organic counterion.Type: GrantFiled: September 5, 2008Date of Patent: August 14, 2012Assignee: Korea Kumho Petrochemical Co., Ltd.Inventors: Sung-Do Jung, Jin-Ho Kim, Jung-Hoon Oh, Hyun-Soon Lim
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Patent number: 8236477Abstract: A positive resist composition including a base component (A) which exhibits increased solubility in an alkali developing solution under action of acid and an acid-generator component (B) which generates acid upon exposure, the base component (A) including a polymeric compound (A1) containing a structural unit (a0) represented by general formula (a0-1), a structural unit (a1) derived from an acrylate ester containing an acid dissociable, dissolution inhibiting group, and a structural unit (a3) derived from an acrylate ester containing a hydroxy group-containing aliphatic hydrocarbon group represented by general formula (a3-1), and the amount of the structural unit (a3) based on the combined total of all structural units constituting the polymeric compound (A1) being in the range of 1 to 30 mol %.Type: GrantFiled: December 2, 2009Date of Patent: August 7, 2012Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Tasuku Matsumiya, Daiju Shiono, Tomoyuki Hirano, Takahiro Dazai, Kotaro Endo
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Patent number: 8232039Abstract: A polymer comprising a structural unit represented by the formula (I): wherein R1 represents a hydrogen atom or a methyl group, X represents a linear or branched chain C1-C6 alkylene group, Z represents a group represented by the formula (Ia): wherein R2 is independently in each occurrence a linear or branched chain C1-C6 alkyl group and m represents an integer of 0 to 15, and a structural unit represented by the formula (II): wherein R3 represents a hydrogen atom or a methyl group, R4 is independently in each occurrence a linear or branched chain C1-C6 alkyl group and n represents an integer of 0 to 4.Type: GrantFiled: November 4, 2009Date of Patent: July 31, 2012Assignee: Sumitomo Chemical Company, LimitedInventors: Nobuo Ando, Kazuhiko Hashimoto
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Patent number: 8232040Abstract: A positive resist composition including a base material component (A) that exhibits increased solubility in an alkali developing solution under action of an acid; and an acid generator component (B) that generates an acid upon exposure, wherein the base material component (A) includes a polymeric compound (A1) having a structural unit (a10) derived from hydroxystyrene and a structural unit (a11) represented by general formula (a11-1) shown below: wherein R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms, or a halogenated alkyl group of 1 to 5 carbon atoms; R21 represents an alkyl group; and R22 represents a group that forms an aliphatic monocyclic group of 7 to 10-membered ring together with the carbon atom to which this R22 group is bonded.Type: GrantFiled: November 17, 2009Date of Patent: July 31, 2012Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Jun Iwashita, Takeyoshi Mimura
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Patent number: 8232041Abstract: A polymeric compound (A1) includes a structural unit (a0-1) represented by general formula (a0-1), a structural unit (a0-2) represented by general formula (a0-2), and a structural unit (a1-0-1) represented by general formula (a1-0-1), wherein relative to the combined total of all the structural units, the proportion of the structural unit (a0-1) is from 10 to 40 mol %, the proportion of the structural unit (a0-2) is from 5 to 20 mol %, and the proportion of the structural unit (a1-0-1) is from 10 to 55 mol %. [In the formulas, each of R1 and R independently represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms, or a halogenated alkyl group of 1 to 5 carbon atoms, R2, A and B each represents a divalent linking group, R3 represents a cyclic group containing —SO2— within the ring skeleton thereof, and R4 and X1 each represents an acid-dissociable, dissolution-inhibiting group.Type: GrantFiled: January 26, 2010Date of Patent: July 31, 2012Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Takahiro Dazai, Tomoyuki Hirano, Tasuku Matsumiya, Daiju Shiono
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Patent number: 8227170Abstract: A resist composition including a base component (A) which exhibits changed solubility in an alkali developing solution under action of an acid, and an acid generator component (B), wherein the base component (A) includes a polymeric compound (A0) containing a structural unit (a0) represented by the general formula (a0-1) shown below: (wherein, R1 represents a hydrogen atom, an alkyl group or a halogenated alkyl group; R2 represents a bivalent linking group containing at least one kind of polar groups selected from the group consisting of —O—, —C(?O)—, —C(?O)—O—, a carbonate linkage (—O—C(?O)—O—), —S—, —S(?O)2—, —S(?O)2—O—, —NH—, —NR04— (wherein, R04 represents an alkyl group or an acyl group), and —NH—C(?O)—; and R3 represents a cyclic group containing a sulfonyl group within the ring skeleton).Type: GrantFiled: January 11, 2010Date of Patent: July 24, 2012Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Takahiro Dazai, Daiju Shiono, Tomoyuki Hirano, Tasuku Matsumiya, Daichi Takaki, Takayoshi Mori, Junichi Tsuchiya
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Patent number: 8227169Abstract: There are provided a compound preferable as an acid generator for a resist composition, an acid generator including the compound, a resist composition containing the acid generator, and a method of forming a resist pattern using the resist composition, and the compound is represented by general formula (b1-12) shown below: R2—CH2—O—Y1—SO3?A+??(b1-12) wherein R2 represents a monovalent aromatic organic group; Y1 represents an alkylene group of 1 to 4 carbon atoms which may be fluorinated; and A+ represents a cation.Type: GrantFiled: April 4, 2008Date of Patent: July 24, 2012Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Akiya Kawaue, Yoshiyuki Utsumi, Takehito Seo, Hideo Hada, Kotaro Endo, Daisuke Kawana, Yasuhiro Yoshii, Tsuyoshi Kurosawa
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Patent number: 8221956Abstract: A resist composition for immersion exposure including: a fluorine-containing polymeric compound (F) containing a structural unit (f1) having a base dissociable group and a structural unit (f2) represented by general formula (f2-1) (wherein R represents a hydrogen atom, a lower alkyl group or a halogenated lower alkyl group; and W is a group represented by any one of general formulas (w-1) to (w-4)); 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.Type: GrantFiled: June 18, 2009Date of Patent: July 17, 2012Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Daiju Shiono, Tomoyuki Hirano, Sanae Furuya, Takahiro Dazai, Hiroaki Shimizu, Tsuyoshi Kurosawa, Hideto Nito, Tsuyoshi Nakamura
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Patent number: 8216764Abstract: A positive resist composition including a resin component (A) which exhibits increased alkali solubility under action of acid and an acid-generator component (B) which generates acid upon exposure, the resin component (A) including a structural unit (a1) derived from an acrylate ester having a tertiary alkyl ester-type acid dissociable, dissolution inhibiting group containing an aliphatic monocyclic group and/or an aliphatic branched, tertiary alkyl ester-type acid dissociable, dissolution inhibiting group, and the acid-generator component (B) including an acid generator (B1) having a cation moiety represented by general formula (b?-1) shown below: wherein each of R1 and R2 independently represents a naphthyl group which may have a substituent; and R3 represents an alkyl group or an aryl group exclusive of a naphthyl group.Type: GrantFiled: May 18, 2007Date of Patent: July 10, 2012Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventor: Masaru Takeshita
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Patent number: 8211615Abstract: The present invention provides a copolymer which can prevent problems associated with immersion lithography (including occurrence of a pattern defect such as water mark, and variation in sensitivity or abnormal patterning due to elution of an additive such as a radiation-sensitive acid-generator) and which provides surface characteristics suitable for immersion lithography, and a composition containing the copolymer.Type: GrantFiled: October 30, 2007Date of Patent: July 3, 2012Assignee: Maruzen Petrochemical Co., Ltd.Inventors: Takanori Yamagishi, Tomo Oikawa, Takayoshi Okada
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Patent number: 8211618Abstract: A positive resist composition comprising as a base resin a polymer having carboxyl groups whose hydrogen is substituted by an acid labile group of acenaphthene structure exhibits a high contrast of alkaline dissolution rate before and after exposure, a high resolution, a good pattern profile and minimal LER after exposure, a significant effect of suppressing acid diffusion rate, and improved etching resistance.Type: GrantFiled: March 8, 2010Date of Patent: July 3, 2012Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Jun Hatakeyama, Koji Hasegawa, Seiichiro Tachibana
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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: 8202680Abstract: Various lithography methods are disclosed herein. In an example, a method includes forming a resist layer over a substrate; forming a coating material layer that includes one of an acid and a chelate compound over the resist layer; and exposing the resist layer and the coating material layer to radiation, wherein during the exposing, the one of the acid and the chelate compound in the coating material layer substantially neutralizes any quencher that diffuses into the coating material layer from the resist layer.Type: GrantFiled: July 7, 2011Date of Patent: June 19, 2012Assignee: Taiwan Semiconductor Manufacturing Company, Ltd.Inventor: Ching-Yu Chang
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Patent number: 8192914Abstract: A resist composition for immersion exposure and a method of forming a resist pattern are provided which can satisfy both of excellent resistance to an immersion medium and lithography properties. The resist composition for immersion exposure includes a resin component (A) which exhibits changed alkali solubility under action of acid and an acid-generator component (B) which generates acid upon irradiation, the resin component (A) including a resin (A1) which contains a fluorine atom and a resin (A2) which has a structural unit (a?) derived from acrylic acid and contains no fluorine atom, and the amount of the resin (A1) contained in the resin component (A) being within the range from 0.1 to 50% by weight.Type: GrantFiled: December 8, 2006Date of Patent: June 5, 2012Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventor: Makiko Irie
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Patent number: 8182977Abstract: A polymer includes a repeating unit (a-1) shown by a following formula (a-1), a repeating unit (a-2) shown by a following formula (a-2), and a GPC weight average molecular weight of about 1000 to about 100,000, wherein R0 represents an alkyl group having 1 to 5 carbon atoms in which at least one hydrogen atom is substituted by a hydroxyl group, and R1 represents a hydrogen atom, a methyl group, or a trifluoromethyl group, wherein R1 represents a hydrogen atom, a methyl group, or a trifluoromethyl group, R2 represents an alkyl group having 1 to 4 carbon atoms, and R3 represents an alkyl group having 1 to 4 carbon atoms, a substituted or unsubstituted monovalent cyclic hydrocarbon group having 4 to 20 carbon atoms, or a divalent cyclic hydrocarbon group having 4 to 20 carbon atoms formed by R3 and R3 bonding to each other together with a carbon atom.Type: GrantFiled: March 23, 2010Date of Patent: May 22, 2012Assignee: JSR CorporationInventors: Norihiko Ikeda, Hiromitsu Nakashima, Saki Harada
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Patent number: 8173352Abstract: A resist composition comprising: (A) a resin comprising a structural unit having an acid-labile group in its side chain and a structural unit represented by the formula (I): wherein R1 represents a hydrogen atom or a methyl group, Z1 represents a single bond or —(CH2)k—CO—O—, k represents an integer of 1 to 4, and ring X represents an unsubstituted or substituted C3-C30 cyclic hydrocarbon group having —COO—, (B) a resin comprising a structural unit having an acid-labile group in its side chain and a structural unit represented by the formula (III): wherein R6 represents a hydrogen atom or a methyl group, R7 is independently in each occurrence a linear or branched chain C1-C6 alkyl group and n represents an integer of 0 to 4, and (C) an acid generator.Type: GrantFiled: November 30, 2009Date of Patent: May 8, 2012Assignee: Sumitomo Chemical Company, LimitedInventor: Nobuo Ando
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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: 8173354Abstract: A sulfonium salt having a triphenylsulfonium cation and a sulfite anion within the molecule is best suited as a photoacid generator in chemically amplified resist compositions. Upon exposure to high-energy radiation, the sulfonium salt generates a sulfonic acid, which facilitates efficient scission of acid labile groups in chemically amplified positive resist compositions. Because of substantial non-volatility under high vacuum conditions in the EB or EUV lithography, the risk of the exposure tool being contaminated is minimized.Type: GrantFiled: July 7, 2010Date of Patent: May 8, 2012Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Youichi Ohsawa, Masaki Ohashi
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Patent number: 8168366Abstract: The present invention relates to a radiation sensitive photoresist composition. The composition comprises a polymer comprising at least two monomers. The first monomer has an acid cleavable tertiary ester group. The second monomer is an acidic monomer. The acid cleavable ester group of the polymer has a surprisingly low activation energy which results in improved resist images in lithographic processes.Type: GrantFiled: October 16, 2008Date of Patent: May 1, 2012Assignee: International Business Machines CorporationInventors: Robert David Allen, Richard Anthony DiPietro, Ratnam Sooriyakumaran, Hoa D Truong
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Patent number: 8158327Abstract: A compound represented by the following formula (1) is provided: wherein R1 represents a hydrogen atom, a trifluoromethyl group, an alkyl group, or an alkoxy group; and A represents a group represented by the following formula (2) or formula (3): wherein R2, R3, R4, R5 and R6 each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted allyl group, a substituted or unsubstituted perfluoroalkyl group, a substituted or unsubstituted benzyl group, or a substituted or unsubstituted aryl group; and two or more of R2, R3 and R4 may be linked to each other to form a saturated or unsaturated carbon ring or a saturated or unsaturated heterocyclic ring. The chemically amplified resist composition comprising a polymer compound which is produced from the compound of formula 1 according to the present invention provides a chemically amplified resist sensitive to far-ultraviolet radiation, which is represented by KrF excimer laser or ArF excimer laser.Type: GrantFiled: January 15, 2009Date of Patent: April 17, 2012Assignee: Korea Kumho Petrochemical Co., Ltd.Inventors: Hyun-Sang Joo, Joo-Hyeon Park, Jung-Hoon Oh, Dae-Hyeon Shin
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Patent number: 8158330Abstract: A protective coating composition comprising a copolymer of an alkali-soluble (?-trifluoromethyl) acrylate and a norbornene derivative as a base polymer, optionally in admixture with a second polymer containing sulfonic acid and/or sulfonic acid amine salt in repeat units is applied onto a resist film. The protective coating is effective in minimizing development defects and forming a resist pattern of improved profile.Type: GrantFiled: May 11, 2009Date of Patent: April 17, 2012Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Yuji Harada, Jun Hatakeyama, Koji Hasegawa, Satoshi Shinachi
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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: 8142979Abstract: A resist composition for immersion exposure, including a base component (A) that exhibits changed solubility in an alkali developing solution under action of acid, an acid generator component (B) that generates acid upon exposure, and a fluorine-containing compound (C) represented by general formula (c-1) (in formula (c-1), R1 represents an organic group which may contain a polymerizable group; X represents a divalent organic group having an acid dissociable portion; and R2 represents an organic group having a fluorine atom).Type: GrantFiled: June 10, 2009Date of Patent: March 27, 2012Assignee: Tokyo Ohka Tokyo Co., Ltd.Inventors: Tsuyoshi Kurosawa, Hiroaki Shimizu
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Patent number: 8137892Abstract: Disclosed is a photobase generator comprising a compound having a nitrogen atom and a conjugated multiple bond.Type: GrantFiled: December 12, 2007Date of Patent: March 20, 2012Assignee: Asahi Kasei Chemicals CorporationInventors: Katsuya Shimizu, Fumio Matsushita
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Patent number: 8137889Abstract: Disclosed is a solvent for printing which comprises a first solvent selected from the group consisting of acetone, methyl ethyl ketone, methyl acetate, ethyl acetate, methanol and mixtures thereof, and a second solvent selected from the group consisting of propylene glycol monomethyl ether acetate (PGMEA), propylene glycol monomethyl ether (PGME), isopropanol, butyl acetate, ethyl-3-ethoxypropionate and mixtures thereof. Further disclosed are a pattern composition for printing comprising the solvent for printing, and a patterning method using the composition. The use of the solvent for printing enables formation of an accurate pattern.Type: GrantFiled: December 27, 2005Date of Patent: March 20, 2012Assignee: LG Display Co., Ltd.Inventors: Hong Suk Yoo, Chul Ho Kim, Jung Jae Lee, Tae Young Oh
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Patent number: 8137891Abstract: A singe- or multilayer lithographic printing plate precursor comprises on a substrate a radiation-sensitive coating that comprises a copolymer soluble or dispersible in aqueous alkaline solution and comprising (meth)acryl recurring units, imide recurring units, and amide recurring units derived from corresponding ethylenically unsaturated polymerizable monomers; the copolymer provides increased chemical resistance for the lithographic printing plate precursors which can be negatively or positively working.Type: GrantFiled: April 12, 2007Date of Patent: March 20, 2012Assignee: Eastman Kodak CompanyInventors: Mathias Jarek, Monika Brummer
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Patent number: 8124314Abstract: A radiation-sensitive composition includes (A) a first polymer which becomes alkali-soluble by the action of an acid and does not contain a fluorine atom, (B) a second polymer having a repeating unit (b1) shown by the following formula (1) and a fluorine-containing repeating unit (b2), and (C) a radiation-sensitive acid generator, the content of the second polymer (B) in the composition being 0.1 to 20 parts by mass relative to 100 parts by mass of the first polymer (A). wherein R1 represents a monovalent organic group, and R8 represents a linear or branched alkyl group having 1 to 12 carbon atoms. The composition can form a resist film capable of suppressing defects inherent to liquid immersion lithography such as watermark defects and bubble defects.Type: GrantFiled: April 1, 2010Date of Patent: February 28, 2012Assignee: JSR CorporationInventors: Yukio Nishimura, Hiromu Miyata
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Patent number: 8114570Abstract: Photoacid generators generate sulfonic acids of formula (1a) upon exposure to high-energy radiation. ROC(?O)R1—COOCH2CF2SO3?H+??(1a) RO is OH or C1-C20 organoxy, R1 is a divalent C1-C20 aliphatic group or forms a cyclic structure with RO. The photoacid generators are compatible with resins and can control acid diffusion and are thus suited for use in chemically amplified resist compositions.Type: GrantFiled: March 24, 2009Date of Patent: February 14, 2012Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Youichi Ohsawa, Takeshi Kinsho, Takeru Watanabe, Koji Hasegawa, Masaki Ohashi
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Patent number: 8110339Abstract: Multi-tone resists can enhance the resolution limit of a lithographic process by advantageously using the changeable solubility of a resist composition as a function of lithographic radiation dosage. By imaging a multi-tone resist with different doses of lithographic radiation in a selected pattern, the pattern can be imparted to the resist upon subsequent development of the resist. In some aspects, a resist composition is utilized having an aliphatic polymer (e.g., a copolymer with fluoropolymer units and/or methacrylate units) with acid labile groups and a plurality of crosslinkable groups that can be crosslinked to other portions of the aliphatic polymer. Other components such as base generators and/or crosslinking agents can also be included. Such compositions can be useful in extending the resolution of UV lithographic radiation processes (e.g., wavelengths less than 200 nm). Other aspects of such compositions and methods are also discussed.Type: GrantFiled: April 17, 2008Date of Patent: February 7, 2012Assignee: Massachusetts Institute of TechnologyInventor: Theodore H. Fedynyshyn
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Patent number: 8105748Abstract: A polymerizable anion-containing sulfonium salt having formula (1) is provided wherein R1 is H, F, methyl or trifluoromethyl, R2, R3 and R4 are C1-C10 alkyl, alkenyl or oxoalkyl or C6-C18 aryl, aralkyl or aryloxoalkyl, or two of R2, R3 and R4 may bond together to form a ring with S, A is a C2-C20 hydrocarbon group having cyclic structure, and n is 0 or 1. The sulfonium salt generates a very strong sulfonic acid upon exposure to high-energy radiation. A resist composition comprising a polymer derived from the sulfonium salt is also provided.Type: GrantFiled: October 16, 2009Date of Patent: January 31, 2012Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Masaki Ohashi, Youichi Ohsawa, Takeshi Kinsho, Jun Hatakeyama, Seiichiro Tachibana
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Patent number: 8105747Abstract: A positive resist composition including a resin component (A) which exhibits changed alkali solubility under action of acid and an acid-generator component (B) which generates acid upon exposure, the resin component (A) including a copolymer (A1) containing a structural unit (a1) represented by general formula (II) or a polymer (A2) consisting of a structural unit (a1) represented by general formula (II) (wherein R represents a hydrogen atom, a halogen atom, a lower alkyl group or a halogenated lower alkyl group; each of R1 to R3 independently represents an alkyl group or a fluorinated alkyl group, with the provision that no fluorine atom is bonded to a carbon atom adjacent to the tertiary carbon atom to which R1 to R3 are bonded, and at least one of R1 to R3 represents a fluorinated alkyl group; and R2 and R3 may form a ring structure).Type: GrantFiled: October 15, 2007Date of Patent: January 31, 2012Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Yoshiyuki Utsumi, Hiroaki Shimizu, Kyoko Ohshita, Yasuhiro Yoshii
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Patent number: 8105749Abstract: There is provided a positive resist composition including a resin component (A) which displays increased solubility in an alkali developing solution under action of acid, and an acid generator component (B) which generates an acid upon exposure, wherein the resin component (A) includes a polymer compound (A1) containing a structural unit (a0) represented by a general formula (a0-1) shown below, and a structural unit (a1) derived from an acrylate ester which has an acid dissociable, dissolution inhibiting group: (in the formula (a0-1), R represents a hydrogen atom, a lower alkyl group, or a halogenated lower alkyl group; two of R? each independently represents a hydrogen atom, a lower alkyl group, or an alkoxy group of 1 to 5 carbon atoms; X represents an alkylene group of 1 to 5 carbon atoms, an oxygen atom, or a sulfur atom.).Type: GrantFiled: June 11, 2010Date of Patent: January 31, 2012Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Takahiro Dazai, Takayoshi Mori, Hiroaki Shimizu, Kyoko Ohshita
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Patent number: 8101335Abstract: A copolymer of an alkali-soluble (?-trifluoromethyl)-acrylate and a norbornene derivative is useful as an additive to a resist composition. When processed by immersion lithography, the resist composition exhibits excellent water repellency and water slip and forms a pattern with few development defects.Type: GrantFiled: May 11, 2009Date of Patent: January 24, 2012Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Yuji Harada, Jun Hatakeyama, Kazunori Maeda, Koji Hasegawa, Satoshi Shinachi
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Patent number: 8101332Abstract: A negative-working lithographic printing plate precursor is disclosed that can be developed on the press without going through a development processing step, and a method of lithographic printing is also disclosed that uses this negative-working lithographic printing plate precursor. A negative-working lithographic printing plate precursor is provided that exhibits excellent on-press developability, nonimage area fine line reproducibility and printing durability and that resists the production of scum during on-press development.Type: GrantFiled: March 27, 2009Date of Patent: January 24, 2012Assignee: Fujifilm CorporationInventors: Norio Aoshima, Yu Iwai
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Patent number: 8097396Abstract: A positive resist composition that includes a resin component (A) that exhibits increased alkali solubility under action of acid, and an acid generator component (B) that generates acid on exposure, wherein the component (A) is a copolymer (A1) that includes a structural unit (a1) derived from an acrylate that contains an acid dissociable, dissolution inhibiting group, a structural unit (a2) derived from an ?-lower alkyl acrylate that contains a lactone ring, and a structural unit (a3) derived from an (?-lower alkyl)acrylate that contains a polar group-containing polycyclic group.Type: GrantFiled: May 25, 2005Date of Patent: January 17, 2012Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Hiroaki Shimizu, Masaru Takeshita
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Patent number: 8092979Abstract: The resist polymer of the present invention comprises a specific constitutional unit having a cyano group, a constitutional unit having an acid-dissociable group, and a specific constitutional unit having a lactone skeleton. When the above polymer is used as a resist resin in DUV excimer laser lithography or electron beam lithography, it exhibits high sensitivity and high resolution, and provides a good resist pattern shape, having a small degree of occurrence of line edge roughness or generation of microgels.Type: GrantFiled: July 1, 2009Date of Patent: January 10, 2012Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Hikaru Momose, Atsushi Ootake, Akifumi Ueda, Tadayuki Fujiwara, Masaru Takeshita, Ryotaro Hayashi, Takeshi Iwai
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Patent number: 8092981Abstract: A negative photoresist composition and a method of manufacturing an array substrate. The negative photoresist composition includes a photocurable composition including an ethylene unsaturated compound containing an ethylene unsaturated bond and a photopolymerization initiator, a thermosetting composition including an alkali-soluble resin crosslinked by heat and an organic solvent. The negative photoresist composition improves stability, photosensitivity, detachability after performing a developing operation and reduces residue to improve the reliability of an organic insulation layer. Furthermore, the negative photoresist composition improves the transmittance of an organic insulation layer and reduces the variation of color coordinates to improve the display quality of a display apparatus.Type: GrantFiled: December 29, 2008Date of Patent: January 10, 2012Assignees: Samsung Electronics Co., Ltd., Techno Semichem Co., Ltd.Inventors: Hoon Kang, Jae-Sung Kim, Yang-Ho Jung, Hi-Kuk Lee, Yasuhiro Kameyama, Yuuji Mizuho, Jong-Cheol Kim, Se-Jin Choi
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Patent number: 8088561Abstract: A method of making a lithographic printing plate includes the steps of: a) providing a lithographic printing plate precursor including (i) a support having a hydrophilic surface or which is provided with a hydrophilic layer, (ii) a coating on the support including an imaging layer, and, optionally, an intermediate layer between the imaging layer and the support, wherein the imaging layer includes a switchable polymer, b) image-wise exposing the coating, whereby the polymer undergoes a chemical reaction induced by the exposing step thereby creating a lithographic image consisting of printing areas and non-printing areas wherein the non-printing areas are removable from the support by a gum solution, and c) developing the precursor by treating the coating of the precursor with the gum solution thereby removing the non-printing areas.Type: GrantFiled: November 23, 2006Date of Patent: January 3, 2012Assignee: Agfa Graphics NVInventors: Hieronymus Andriessen, Hubertus Van Aert, Alexander Williamson, Marc Van Damme
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Patent number: 8088556Abstract: To provide a thiopyran derivative, having a structure expressed by the following general formula 1: where X is O or S; R1 is —H, —CH3, C2-4 alkyl group, thioether group, or ketone group; R2 is —H, —CH3, or trifluoromethyl group; and R1 and R2 may be identical to or different from each other.Type: GrantFiled: May 19, 2010Date of Patent: January 3, 2012Assignee: Fujitsu LimitedInventor: Koji Nozaki
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Patent number: 8088553Abstract: A positive resist composition including a base component (A) which exhibits increased solubility in an alkali developing solution under action of acid and an acid-generator component (B) which generates acid upon exposure, the base component (A) including a polymeric compound (A1) having a structural unit (a0-1) represented by general formula (a0-1) (wherein R1 represents a hydrogen atom, a lower alkyl group or a halogenated lower alkyl group; R8 represents a divalent linking group; and R7 represents an acid dissociable, dissolution inhibiting group) and a structural unit (a0-2) represented by general formula (a0-2) (wherein R3 represents a hydrogen atom, a lower alkyl group or a halogenated lower alkyl group; R4 represents a branched alkyl group of 3 or more carbon atoms; and each of R5 and R6 independently represents an alkyl group, wherein R5 and R6 are mutually bonded to form a ring).Type: GrantFiled: April 17, 2009Date of Patent: January 3, 2012Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Hiroaki Shimizu, Tsuyoshi Nakamura, Takayoshi Mori, Sanae Furuya, Daiju Shiono, Tomoyuki Hirano, Takahiro Dazai
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Patent number: 8088550Abstract: A positive resist composition, includes: (A) a compound capable of generating an acid upon irradiation with actinic rays or radiation; (B) a resin of which solubility in an alkali developer increases under an action of an acid; (C) a compound capable of decomposing under an action of an acid to generate an acid; and (D) a compound which itself acts as a base for the acids generated from the component (A) and the component (C) but decomposes upon irradiation with actinic rays or radiation to lose a basicity for the acids generated from the component (A) and the component (C).Type: GrantFiled: July 29, 2008Date of Patent: January 3, 2012Assignee: Fujifilm CorporationInventors: Shinji Tarutani, Hideaki Tsubaki, Kenji Wada
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Patent number: 8084188Abstract: A radiation-sensitive resin composition includes an acid-dissociable group-containing resin, a radiation-sensitive acid generator, and a solvent. The acid-dissociable group-containing resin includes a copolymer containing a repeating unit. The reparing unit includes an acid-dissociable group-containing repeating unit in an amount of more than about 55 mol % of a total amount of the repeating units in the copolymer. A content of the copolymer in the acid-dissociable group-containing resin is about 90 mass % or more of a total amount of the acid-dissociable group-containing resin.Type: GrantFiled: September 11, 2009Date of Patent: December 27, 2011Assignee: JSR CorporationInventors: Noboru Otsuka, Takanori Kawakami
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Patent number: 8080361Abstract: A positive photosensitive composition includes: a resin (A) whose dissolution rate in an alkaline developing solution increases by the action of an acid, the resin (A) containing an acid decomposable repeating unit represented by a general formula (I) and an acid nondecomposable repeating unit represented by a general formula (II); and a compound (B) capable of generating an acid upon irradiation with one of active rays and radiations: wherein Xa1 represents one of a hydrogen atom, an alkyl group, a cyano group, and a halogen atom, A1 represents one of a single bond and a divalent connecting group, ALG represents an acid leaving hydrocarbon group, Xa2 represents one of a hydrogen atom, an alkyl group, a cyano group, and a halogen atom, A2 represents one of a single bond and a divalent connecting group, and ACG represents an acid nonleaving hydrocarbon group.Type: GrantFiled: January 24, 2007Date of Patent: December 20, 2011Assignee: FUJIFILM CorporationInventors: Hyou Takahashi, Naoya Sugimoto, Kunihiko Kodama, Kei Yamamoto
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Patent number: 8080365Abstract: To provide a thiopyran derivative, having a structure expressed by the following general formula 1: where X is O or S; R1 is —H, —CH3, C2-4 alkyl group, thioether group, or ketone group; R2 is —H, —CH3, or trifluoromethyl group; and R1 and R2 may be identical to or different from each other.Type: GrantFiled: June 15, 2010Date of Patent: December 20, 2011Assignee: Fujitsu LimitedInventor: Koji Nozaki
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Patent number: 8071270Abstract: The present invention provides a polyhydric compound represented by the formula (I): wherein R51 to R67 each independently represent a hydrogen atom etc., at least one selected from the group consisting of R1 to R5 is a group represented by the formula (II): wherein Q1 and Q2 each independently represent a fluorine atom etc., U represents a C1-C20 divalent hydrocarbon group etc., and A+ represents an organic counter ion, and the others are hydrogen atoms or groups represented by the formula (III): wherein X1 to X4 each independently represent a hydrogen atom etc., n represents an integer of 0 to 3, W represents any one of the following groups: Z1 represents a C1-C6 alkyl group etc., and ring Y represents a C3-C20 alicyclic hydrocarbon group, and a chemically amplified resist composition containing the same.Type: GrantFiled: February 23, 2009Date of Patent: December 6, 2011Assignee: Sumitomo Chemical Company, LimitedInventors: Ichiki Takemoto, Nobuo Ando
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Patent number: 8062825Abstract: A positive resist composition having excellent size controllability, and a resist pattern forming method are provided. This positive resist composition contains a resin component (A) comprising an alkali soluble constituent unit (a1) which comprises a constituent unit (a11) derived from (?-methyl)hydroxystyrene, and a constituent unit (a2) which has an acid dissociable dissolution inhibiting group including an acid dissociable dissolution inhibiting group (II) represented by the following general formula (II) and/or a specific chain acid dissociable dissolution inhibiting group (III); an acid generator component (B) which generates an acid upon exposure; and preferably contains an aromatic amine (C).Type: GrantFiled: November 28, 2005Date of Patent: November 22, 2011Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Tomoyuki Ando, Takako Hirosaki
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Patent number: 8062831Abstract: Carboxyl-containing lactone compounds having formula (1) are novel wherein R1 is H, F, methyl or trifluoromethyl, R2 and R3 are H or monovalent hydrocarbon groups, or R2 and R3 may together form an aliphatic ring, W is CH2, O or S, k1 is an integer of 0 to 4, and k2 is 0 or 1. They are useful as monomers to produce polymers which are transparent to radiation?500 nm. Radiation-sensitive resist compositions comprising the polymers as base resin exhibit excellent properties including resolution, LER, pattern density dependency and exposure margin.Type: GrantFiled: May 1, 2009Date of Patent: November 22, 2011Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Satoshi Shinachi, Tsunehiro Nishi, Koji Hasegawa, Takeshi Kinsho, Seiichiro Tachibana, Takeru Watanabe
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Patent number: 8062828Abstract: A positive resist composition comprises a polymer comprising recurring units having a sulfonium salt incorporated therein as a base resin which becomes soluble in alkaline developer under the action of acid. The polymer generates a strong sulfonic acid upon exposure to high-energy radiation so as to facilitate effective scission of acid labile groups in the resist composition.Type: GrantFiled: February 13, 2009Date of Patent: November 22, 2011Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Youichi Ohsawa, Takeshi Kinsho, Masaki Ohashi, Seiichiro Tachibana, Takeru Watanabe, Jun Hatakeyama
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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