Polymer Of Unsaturated Acid Or Ester Patents (Class 430/910)
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Patent number: 11940730Abstract: Disclosed herein is a pattern formation method, comprising (a) applying a layer of a photoresist composition over a semiconductor substrate, (b) pattern-wise exposing the photoresist composition layer to i-line radiation; and (c) developing the exposed photoresist composition layer to provide a resist relief image; wherein the photoresist composition comprises a non-ionic photoacid generator; a solvent; a first polymer and a second polymer; and wherein the first polymer comprises a polymeric dye.Type: GrantFiled: December 29, 2021Date of Patent: March 26, 2024Assignee: ROHM AND HAAS ELECTRONIC MATERIALS LLCInventors: Mitsuru Haga, Mingqi Li
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Patent number: 11673984Abstract: Provided is a binder composition for a non-aqueous secondary battery electrode that can form a slurry composition for a non-aqueous secondary battery electrode having excellent viscosity stability and a non-aqueous secondary battery having excellent cycle characteristics. The binder composition for a non-aqueous secondary battery electrode contains: a polymer that includes a monomer unit including a functional group that is bondable with a cationic group and a (meth)acrylic acid ester monomer unit; and an organic compound that includes at least two cationic groups. The binder composition for a non-aqueous secondary battery electrode has a viscosity change rate of 400% or less when left at rest at a temperature of 60° C. for 30 days.Type: GrantFiled: March 14, 2019Date of Patent: June 13, 2023Assignee: ZEON CORPORATIONInventors: Tomoya Murase, Taku Matsumura
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Patent number: 9040220Abstract: A resist composition including a base component which exhibits changed solubility in an alkali developing solution under action of acid and an acid-generator component which generates acid upon exposure, the acid-generator including an acid generator consisting of a compound represented by general formula (b1-1) shown below: In which RX represents a hydrocarbon group which may have a substituent exclusive of a nitrogen atom; each of Q2 and Q3 independently represents a single bond or a divalent linkage group; Y1 represents an alkylene group or fluorinated alkyl group of 1 to 4 carbon atoms; and Z+ represents an organic cation exclusive of an ion represented by general formula (w-1).Type: GrantFiled: March 2, 2012Date of Patent: May 26, 2015Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Hideo Hada, Yoshiyuki Utsumi, Keita Ishiduka, Kensuke Matsuzawa, Fumitake Kaneko, Kyoko Ohshita, Hiroaki Shimizu, Yasuhiro Yoshii
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Patent number: 9034556Abstract: 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 (b1-1) shown below: wherein RX represents a hydrocarbon group which may have a substituent exclusive of a nitrogen atom; each of Q2 and Q3 independently represents a single bond or a divalent linkage group; Y1 represents an alkylene group or fluorinated alkyl group of 1 to 4 carbon atoms; and Z+ represents an organic cation exclusive of an ion represented by general formula (w-1).Type: GrantFiled: December 18, 2008Date of Patent: May 19, 2015Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Hideo Hada, Yoshiyuki Utsumi, Keita Ishiduka, Kensuke Matsuzawa, Fumitake Kaneko, Kyoko Ohshita, Hiroaki Shimizu, Yasuhiro Yoshii
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Patent number: 9023581Abstract: A resist composition which can form a very fine resist pattern with excellent lithography properties, a new polymeric compound useful for the resist composition, and a compound useful as a monomer for the polymeric compound. The resist composition contains a polymeric compound containing a structural unit (a0) represented by general formula (a0) shown below. In the formula (a0), A is an anion represented by the general formula (1) or (2).Type: GrantFiled: June 14, 2011Date of Patent: May 5, 2015Assignee: Tokyo Ohka Kogyo Co., LtdInventors: Akiya Kawaue, Kazushige Dohtani, Yoshiyuki Utsumi, Jun Iwashita, Kenri Konno, Daiju Shiono, Daichi Takaki
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Patent number: 9017931Abstract: A negative pattern is formed by coating a resist composition comprising a polymer comprising recurring units having a tertiary ester type acid labile group having a plurality of methyl or ethyl groups on alicycle and an acid generator onto a substrate, prebaking, exposing to high-energy radiation, baking, and developing in an organic solvent developer so that the unexposed region of resist film is dissolved away and the exposed region of resist film is not dissolved. The resist composition exhibits a high dissolution contrast during organic solvent development and forms a fine hole or trench pattern of dimensional uniformity.Type: GrantFiled: August 16, 2013Date of Patent: April 28, 2015Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Koji Hasegawa, Jun Hatakeyama, Masayoshi Sagehashi, Teppei Adachi
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Patent number: 9017918Abstract: A polymer is obtained from a hydroxyphenyl methacrylate monomer having an acid labile group substituted thereon. A positive resist composition comprising the polymer as a base resin has a very high contrast of alkaline dissolution rate before and after exposure, a high resolution, a good profile and minimal line edge roughness of a pattern after exposure, a retarded acid diffusion rate, and good etching resistance.Type: GrantFiled: June 1, 2011Date of Patent: April 28, 2015Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Jun Hatakeyama, Seiichiro Tachibana, Koji Hasegawa
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Patent number: 9012129Abstract: 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) including a compound represented by (b1-1), a compound represented by (b1-1?) and/or a compound represented by (b1-1?) (R1?-R3? represents an aryl group or an alkyl group, provided that at least one of R1?-R3? represents a substituted aryl group being substituted with a group represented by (b1-1-0), and two of R1?-R3? may be mutually bonded to form a ring with the sulfur atom; X represents a C3-C30 hydrocarbon group; Q1 represents a carbonyl group-containing divalent linking group; X10 represents a C1-C30 hydrocarbon group; Q3 represents a single bond or a divalent linking group; Y10 represents —C(?O)— or —SO2—; Y11 represents a C1-C10 alkyl group or a fluorinated alkyl group: Q2 represents a single bond or an alkylene group; and W represents a C2-C10 alkylene group).Type: GrantFiled: January 6, 2014Date of Patent: April 21, 2015Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Hideo Hada, Yoshiyuki Utsumi, Takehiro Seshimo, Akiya Kawaue
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Patent number: 9012123Abstract: A positive resist composition and a pattern forming method using the resist composition are provided, the resist composition including: (A) a resin containing a repeating structural unit represented by formula (I) as defined in the specification and being capable of decomposing by an action of an acid to increase the solubility in an alkali developer; (B) an acid generator; and (C) a mixed solvent containing at least one solvent selected from the group consisting of the following Group (a) and at least one solvent selected from the group consisting of the following Groups (b) to (d): Group (a): an alkylene glycol monoalkyl ether, Group (b): an alkylene glycol monoalkyl ether carboxylate, Group (c): a linear ketone, a branched chain ketone, a cyclic ketone, a lactone and an alkylene carbonate, and Group (d): a lactic acid ester, an acetic acid ester and an alkoxypropionic acid ester.Type: GrantFiled: March 26, 2009Date of Patent: April 21, 2015Assignee: FUJIFILM CorporationInventors: Kei Yamamoto, Akinori Shibuya
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Patent number: 8999621Abstract: A pattern forming method includes: (i) forming a film from a chemical amplification resist composition; (ii) exposing the film, so as to form an exposed film; and (iii) developing the exposed film by using an organic solvent-containing developer, wherein the chemical amplification resist composition contains: (A) a resin substantially insoluble in alkali; (B) a compound capable of generating an acid upon irradiation with an actinic ray or radiation; (C) a crosslinking agent; and (D) a solvent, a negative chemical amplification resist composition used in the method, and a resist film formed from the negative chemical amplification resist composition.Type: GrantFiled: October 5, 2010Date of Patent: April 7, 2015Assignee: FUJIFILM CorporationInventors: Yuichiro Enomoto, Sou Kamimura, Shinji Tarutani, Keita Kato, Kaoru Iwato
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Patent number: 8993212Abstract: A resist composition according to the present invention includes at least a base resin, a photoacid generator and a solvent, wherein the photoacid generator comprises a fluorine-containing sulfonic acid salt of the following general formula (4). In the formula, X independently represents a hydrogen atom or a fluorine atom; n represents an integer of 1 to 6; R1 represents a hydrogen atom, or an alkyl, alkenyl, oxoalkyl, aryl or aralkyl group; any of hydrogen atoms on carbons in R1 may be substituted with a substituent; R2 represents RAO or RBRCN; and A represents a divalent group. This fluorine-containing sulfonic acid salt can serve as a photoacid generator having high solubility in a resist solvent and thus can suitably be used for a resist composition such that the resist composition shows high resolution, wide DOF, small LER and high sensitivity to form a good pattern shape in lithographic processes.Type: GrantFiled: October 14, 2011Date of Patent: March 31, 2015Assignee: Central Glass Company, LimitedInventors: Ryozo Takihana, Satoru Narizuka
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Patent number: 8980524Abstract: A positive resist composition including a base component (A) which exhibits increased solubility in an alkali developing solution under action of acid, an acid-generator component (B) which generates acid upon exposure and a fluorine-containing polymeric compound (C?) which generates acid upon exposure, the base component (A) having a structural unit (a0-1) represented by general formula (a0-1) and a structural unit (a1) derived from an acrylate ester containing an acid dissociable, dissolution inhibiting group, and the fluorine-containing polymeric compound (C?) having a structural unit (c0) which generates acid upon exposure and a structural unit (c1) represented by formula (c1) (wherein R2 represents a divalent linking group, R3 represents a cyclic group containing —SO2— within the ring skeleton, Q0 represents a single bond or a divalent linking group, and R0 represents an organic group which may have a fluorine atom).Type: GrantFiled: December 27, 2010Date of Patent: March 17, 2015Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Tomoyuki Hirano, Daiju Shiono, Masatoshi Arai
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Patent number: 8968979Abstract: A positive resist composition comprises a polymer comprising repeat units having formula (1) or (2). Herein denotes an aromatic hydrocarbon group, R1 is H, methyl or trifluoromethyl, R2 is H, C1-C12 alkyl or aromatic hydrocarbon group, R3 is C1-C12 alkyl, or R2 and R3 may bond together to form a ring, and a is 1 or 2. When used in the ArF lithography, the resist composition exhibits high resolution. When used in the EB image writing for mask processing, the resist composition exhibits high resolution and sensitivity sufficient to comply with high-accelerating-voltage EB irradiation, and high etch resistance.Type: GrantFiled: November 20, 2009Date of Patent: March 3, 2015Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Katsuya Takemura, Keiichi Masunaga, Daisuke Domon, Masayoshi Sagehashi
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Patent number: 8969483Abstract: A photoresist material comprising a polymer with at least two acrylate derivatives incorporated therein, and a photo-acid generator for generating an acid by exposure, wherein at least one of the two acrylate derivatives incorporated therein comprises a norbornyl moiety having a lactone structure, and at least one of the two acrylate derivatives comprises an ester-substituted tetracyclododecyl moiety.Type: GrantFiled: November 28, 2012Date of Patent: March 3, 2015Assignee: NEC CorporationInventors: Katsumi Maeda, Shigeyuki Iwasa, Kaichiro Nakano, Etsuo Hasegawa
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Patent number: 8962233Abstract: According to one embodiment, an actinic-ray- or radiation-sensitive resin composition includes an arylsulfonium salt that when exposed to actinic rays or radiation, generates an acid, the arylsulfonium salt containing at least one aryl ring on which there are a total of one or more electron donating groups, the acid generated upon exposure to actinic rays or radiation having a volume of 240 ?3 or greater.Type: GrantFiled: January 28, 2011Date of Patent: February 24, 2015Assignee: FUJIFILM CorporationInventors: Takeshi Kawabata, Tomotaka Tsuchimura, Takayuki Ito
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Patent number: 8956803Abstract: The present invention provides a sulfonium salt used in a resist composition that can give a pattern having a high resolution, especially an excellent rectangularity of a pattern form and a small roughness, while not readily generating a defect, in the photolithography using a high energy beam as a light source; a resist composition that contains the sulfonium salt; and a patterning process using this resist composition, wherein the sulfonium salt is shown by the following general formula (1a), wherein each of R and R0 independently represents a hydrogen atom, or a linear, branched, or cyclic monovalent hydrocarbon group having 1 to 30 carbon atoms which may be optionally substituted by a heteroatom or interposed by a heteroatom.Type: GrantFiled: December 6, 2013Date of Patent: February 17, 2015Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Masaki Ohashi, Tomohiro Kobayashi, Akihiro Seki, Masayoshi Sagehashi, Masahiro Fukushima
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Patent number: 8945808Abstract: Resist compositions that can be used in immersion lithography without the use of an additional topcoat are disclosed. The resist compositions comprise a photoresist polymer, at least one photoacid generator, a solvent; and a self-topcoating resist additive. A method of forming a patterned material layer on a substrate using the resist composition is also disclosed.Type: GrantFiled: April 28, 2006Date of Patent: February 3, 2015Assignee: International Business Machines CorporationInventors: Robert Allen David, Phillip Joe Brock, Carl E Larson, Daniel Paul Sanders, Ratnam Sooriyakumaran, Linda Karin Sundberg, Hoa D Truong, Gregory Michael Wallraff
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Patent number: 8945810Abstract: A positive resist composition comprises: (A) a resin that has a repeating unit represented by general formula (a1) and increases its solubility in an alkali developer by action of an acid; (B) a compound which generates an acid upon irradiation with an actinic ray or a radiation; and (C) a resin that has at least one of a fluorine atom and a silicon atom and has a group selected from the group consisting of (x), (y) and (z); and (D) a solvent: (x) an alkali-soluble group; (y) a group capable that decomposes by action of an alkali developer to undergo an increase in a solubility of the resin (C) in an alkali developer; and (z) a group that decomposes by action of an acid, wherein R represents a hydrogen atom or a methyl group, Rxa represents an alkyl group or a cycloalkyl group, and n represents an integer of 1 to 8.Type: GrantFiled: June 30, 2011Date of Patent: February 3, 2015Assignee: FUJIFILM CorporationInventors: Fumiyuki Nishiyama, Hiromi Kanda
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Patent number: 8932797Abstract: A photoacid generator compound has formula (I): G+Z???(I) wherein G has formula (II): In formula (II), X is S or I, each R0 is commonly attached to X and is independently C1-30 alkyl; polycyclic or monocyclic C3-30 cycloalkyl; polycyclic or monocyclic C6-30 aryl; or a combination comprising at least one of the foregoing groups. G has a molecular weight greater than 263.4 g/mol, or less than 263.4 g/mol. One or more R0 groups are further attached to an adjacent R0 group, a is 2 or 3, wherein when X is I, a is 2, or when X is S, a is 2 or 3. Z in formula (I) comprises the anion of a sulfonic acid, a sulfonimide, or a sulfonamide. A photoresist and coated film also includes the photoacid generator, and a method of forming an electronic device uses the photoresist.Type: GrantFiled: November 30, 2011Date of Patent: January 13, 2015Assignees: Dow Global Technologies LLC, Rohm and Haas Electronic Materials LLCInventors: James W. Thackeray, Suzanne M. Coley, James F. Cameron, Paul J. LaBeaume, Ahmad E. Madkour, Owendi Ongayi, Vipul Jain
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Patent number: 8932794Abstract: A positive photosensitive composition, includes: (A) a resin having a repeating unit represented by formula (1) as defined in the specification and a repeating unit represented by formula (2) as defined in the specification and being capable of increasing a solubility of the resin (A) in an alkali developer by an action of an acid; (B) a compound capable of generating an acid upon irradiation with actinic rays or radiation; and a solvent, and a pattern forming method uses the positive photosensitive composition.Type: GrantFiled: September 29, 2009Date of Patent: January 13, 2015Assignee: FUJIFILM CorporationInventors: Toshiaki Fukuhara, Akinori Shibuya, Takayuki Kato
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Patent number: 8921027Abstract: A radiation-sensitive resin composition includes an acid-labile group-containing resin, and a compound shown by the following general formula (i). R1 represents a hydrogen atom or the like, R2 represents a single bond or the like, R3 represents a linear or branched unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms or the like, and X+ represents an onium cation.Type: GrantFiled: December 15, 2011Date of Patent: December 30, 2014Assignee: JSR CorporationInventors: Ryuichi Serizawa, Nobuji Matsumura, Hirokazu Sakakibara
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Patent number: 8921029Abstract: A resist composition having a resin having a structural unit represented by the formula (I), a resin being insoluble or poorly soluble in alkali aqueous solution, but becoming soluble in an alkali aqueous solution by the action of an acid and not including the structural unit represented by the formula (I), and an acid generator represented by the formula (II), wherein R1, A1, R2, RII1, RII2, LII1, YII1, RII3, RII4, RII5, RII6, RII7, n, s and RII8 are defined in the specification.Type: GrantFiled: July 18, 2012Date of Patent: December 30, 2014Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Ichikawa, Yukako Anryu, Shingo Fujita
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Patent number: 8916333Abstract: A radiation-sensitive resin composition includes a polymer and a photoacid generator. The polymer includes a first structural unit shown by a formula (a1), a second structural unit shown by a formula (a2), and a third structural unit having a lactone structure. A content of the first structural unit in the polymer being 50 mol % or more based on total structural units included in the polymer. The first structural unit is preferably a structural unit shown by a formula (a1-1).Type: GrantFiled: September 28, 2012Date of Patent: December 23, 2014Assignee: JSR CorporationInventors: Hiroshi Tomioka, Noboru Otsuka, Akimasa Soyano
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Patent number: 8911928Abstract: A resist composition including a base component (A) that exhibits changed solubility in a developing solution under action of acid and an acid generator component (B) that generates acid upon exposure, wherein the base component (A) contains a resin component (A1) including a structural unit (a0) represented by general formula (a0-1) shown below and a structural unit (a1)) containing an acid decomposable group that exhibits increased polarity under action of acid, and the amount of the structural unit (a0) is less than 50 mol %, 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; R1 represents a divalent linking group; R2 represents a —SO2— containing cyclic group; and v represents 0 or 1.Type: GrantFiled: May 22, 2012Date of Patent: December 16, 2014Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Tomoyuki Hirano, Daiju Shiono, Daichi Takaki, Junichi Tsuchiya
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Patent number: 8900793Abstract: There is disclosed a polymer having a repeating unit shown by the following general formula (1). There can be, in a photolithography using a high energy beam such as an ArF excimer laser beam and an EUV as a light source, (1) a polymer that gives a resist composition having an appropriate adhesion with a substrate and being capable of forming a pattern having excellent resolution, especially an excellent rectangular pattern profile, (2) a chemically amplified resist composition containing the said polymer, and (3) a patterning process using the said chemically amplified resist composition.Type: GrantFiled: May 21, 2012Date of Patent: December 2, 2014Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Masayoshi Sagehashi, Youichi Ohsawa, Koji Hasegawa, Tomohiro Kobayashi
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Patent number: 8900796Abstract: The present invention provides an acid generator generates a sulfonic acid represented by the following general formula (1) in response to high-energy beam or heat: To provide a novel acid generator which is suitably used as an acid generator for a resist composition, which solves the problems of LER and a depth of focus and can be effectively and widely used particularly without degradation of a resolution, a chemically amplified resist composition using the same, and a patterning process.Type: GrantFiled: February 15, 2013Date of Patent: December 2, 2014Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Masaki Ohashi, Tomohiro Kobayashi, Masayoshi Sagehashi
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Patent number: 8900788Abstract: A resist composition for immersion exposure, including: a base component (A) which exhibits changed solubility in an alkali developing solution under action of an acid, and contains no structural unit (c1) represented by the general formula (c1-1) shown below; an acid generator component (B) which generates an acid upon exposure; and a fluorine-containing resin component (C) which contains the structural unit (c1) (in the formula (c1-1), R represents a hydrogen atom, a lower alkyl group, a halogen atom, or a halogenated lower alkyl group; Rf represents a fluorinated alkyl group; and Y0 represents an alkylene group).Type: GrantFiled: October 12, 2007Date of Patent: December 2, 2014Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Yoshiyuki Utsumi, Yasuhiro Yoshii
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Patent number: 8900789Abstract: An actinic-ray- or radiation-sensitive resin composition comprises (A) a resin that when acted on by an acid, exhibits an increased solubility in an alkali developer, (B) a compound that when exposed to actinic rays or radiation, generates an acid, (C) a resin containing two or more resins (c) each having at least either a fluorine atom or a silicon atom, and (D) a solvent.Type: GrantFiled: July 13, 2009Date of Patent: December 2, 2014Assignee: FUJIFILM CorporationInventors: Hiroshi Saegusa, Shinichi Kanna
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Patent number: 8889333Abstract: A salt represented by formula (I): wherein Q1 and Q2 independently each represent a fluorine atom or a C1-C6 perfluoroalkyl group, L1 represents a C1-C17 divalent saturated hydrocarbon group in which a methylene group may be replaced by an oxygen atom or a carbonyl group, L2 and L3 respectively represent a single bond or a C1-C6 divalent saturated alkyl group in which a methylene group may be replaced by an oxygen atom or a carbonyl group, ring W1 and ring W2 respectively represent a C3-C36 hydrocarbon ring, R1 and R2 respectively represent a hydrogen atom or C1-C6 alkyl group, R3 represents C1-C6 alkyl group, t represents an integer of 0 to 2 and Z+ represents an organic counter ion.Type: GrantFiled: April 10, 2012Date of Patent: November 18, 2014Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Ichikawa, Isao Yoshida, Yuko Yamashita
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Patent number: 8877421Abstract: A positive resist composition includes: (A) a resin capable of increasing the solubility in an alkali developing solution by the action of an acid, including: (a1) a repeating unit selected from repeating units represented by following formulae (a1-1) to (a1-3); (a2) a repeating unit represented by a following formula (a2); and (a3) a repeating unit selected from repeating units represented by following formulae (a3-1) to (a3-4); (B) a compound capable of generating an acid upon irradiation with actinic ray or radiation; (C) a resin having at least one of a fluorine atom and a silicon atom, and being insoluble in an alkali developing solution; and (D) a solvent, wherein the formulae above are defined in the specification.Type: GrantFiled: March 28, 2008Date of Patent: November 4, 2014Assignee: FUJIFILM CorporationInventor: Shinichi Kanna
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Patent number: 8877424Abstract: A polymer is prepared from an adamantane methacrylate monomer whose alcoholic hydroxyl group is protected with an alicyclic-containing tertiary alkyl group. A photoresist composition comprising the polymer displays a high sensitivity and a high dissolution contrast during both alkaline development and organic solvent development.Type: GrantFiled: February 8, 2013Date of Patent: November 4, 2014Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Masayoshi Sagehashi, Jun Hatakeyama, Koji Hasegawa, Kazuhiro Katayama
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Patent number: 8859181Abstract: A chemically amplified negative resist composition is provided comprising (A) an alkali-soluble base polymer, (B) an acid generator, and (C) a nitrogen-containing compound, the base polymer (A) turning alkali insoluble under the catalysis of acid. A polymer having a fluorinated carboxylic acid onium salt on a side chain is included as the base polymer. Processing the negative resist composition by a lithography process may form a resist pattern with advantages including uniform low diffusion of acid, improved LER, and reduced substrate poisoning.Type: GrantFiled: February 24, 2011Date of Patent: October 14, 2014Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Keiichi Masunaga, Satoshi Watanabe, Jun Hatakeyama, Youichi Ohsawa, Daisuke Domon
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Patent number: 8859180Abstract: [Task to Be Achieved] To provide a chemically amplified type positive copolymer for semiconductor lithography, which has eliminated the problems of prior art, has a high development contrast, and has excellent resolution in fine-pattern formation; a composition for semiconductor lithography which contains the copolymer; and a process for producing the copolymer. [Means for Achievement] The copolymer for semiconductor lithography according to the present invention is a copolymer which has at least (A) a repeating unit having a structure which has an alkali-soluble group protected by an acid-labile, dissolution-suppressing group, (B) a repeating group having a lactone structure and (C) a repeating group having an alcoholic hydroxyl group and which is characterized by having an acid value of 0.01 mmol/g or less as determined by dissolving the copolymer in a solvent and subjecting the solution to neutralization titration with a solution of an alkali metal hydroxide using Bromothymol Blue as an indicator.Type: GrantFiled: October 19, 2007Date of Patent: October 14, 2014Assignee: Maruzen Petrochemical Co., Ltd.Inventors: Tomo Oikawa, Takayoshi Okada, Masaaki Kudo, Takanori Yamagishi
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Patent number: 8859187Abstract: A novel method of forming a resist pattern in which thickness loss from the resist pattern is reduced, and a negative resist composition that can be used in this method of forming a resist pattern. The method of forming a resist pattern includes: forming a first resist film by applying a first resist composition to a support, forming a first resist pattern by selectively exposing the first resist film through a first mask pattern and then developing the first resist film, forming a second resist film by applying a negative resist composition containing an ether-based organic solvent (S?) having no hydroxyl groups onto the support having the first resist pattern formed thereon, and forming a resist pattern by selectively exposing the second resist film through a second mask pattern and then developing the second resist film.Type: GrantFiled: October 19, 2007Date of Patent: October 14, 2014Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Ken Tanaka, Sho Abe, Shigeru Yokoi
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Patent number: 8846295Abstract: The present invention relates to a photoresist composition capable of negative development and a pattern forming method using the photoresist composition. The photoresist composition includes an imaging polymer, a crosslinking agent and a radiation sensitive acid generator. The imaging polymer includes a monomeric unit having an acid-labile moiety-substituted hydroxyl group. The patterning forming method utilizes an organic solvent developer to selectively remove an unexposed region of a photoresist layer of the photoresist composition to form a patterned structure in the photoresist layer. The photoresist composition and the pattern forming method are especially useful for forming material patterns on a semiconductor substrate using 193 nm (ArF) lithography.Type: GrantFiled: April 27, 2012Date of Patent: September 30, 2014Assignee: International Business Machines CorporationInventors: Kuang-Jung Chen, Wu-Song Huang, Wai-Kin Li
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Patent number: 8846301Abstract: An orthogonal process for photolithographic patterning organic structures is disclosed. The disclosed process utilizes fluorinated solvents or supercritical CO2 as the solvent so that the performance of the organic conductors and semiconductors would not be adversely affected by other aggressive solvent. One disclosed method may also utilize a fluorinated photoresist together with the HFE solvent, but other fluorinated solvents can be used. In one embodiment, the fluorinated photoresist is a resorcinarene, but various fluorinated polymer photoresists and fluorinated molecular glass photoresists can be used as well. For example, a copolymer perfluorodecyl methacrylate (FDMA) and 2-nitrobenzyl methacrylate (NBMA) is a suitable orthogonal fluorinated photoresist for use with fluorinated solvents and supercritical carbon dioxide in a photolithography process.Type: GrantFiled: May 21, 2009Date of Patent: September 30, 2014Assignee: Cornell UniversityInventors: Christopher K. Ober, George Malliaras, Jin-Kyun Lee, Alexander Zakhidov, Margarita Chatzichristidi, Priscilla Taylor
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Patent number: 8846293Abstract: The actinic ray-sensitive or radiation-sensitive resin composition of the present invention contains (A) a resin capable of increasing the solubility in an alkaline developer by the action of an acid, and (C) at least one selected from the group of compounds represented by the following formula (ZI-3), (ZI-4) or (ZI-5) and capable of generating an acid upon irradiation of actinic rays or radiation, wherein the resin (A) contains at least one repeating unit having a group capable of decomposing by the action of an acid to leave a leaving group having a ring structure, and the leaving group having a ring structure has at least one of a polar group as a substituent and a polar atom as a part of the ring structure, and a compound derived from the leaving group having a ring structure has a logP value of not less than 0 and less than 2.8.Type: GrantFiled: March 27, 2012Date of Patent: September 30, 2014Assignee: FUJIFILM CorporationInventors: Yusuke Iizuka, Akinori Shibuya, Naohiro Tango, Shohei Kataoka
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Patent number: 8846294Abstract: The present invention provides a photoresist composition comprising the following components (A), (B) and (X): (A) a resin being insoluble or poorly soluble in an aqueous alkali solution but becoming soluble in an aqueous alkali solution by the action of an acid, (B) an acid generator, (X) at least one compound selected from the group consisting of a compound represented by the formula (I-a): wherein Z1 represent a C1-C20 divalent saturated aliphatic hydrocarbon group in which one or more —CH2— may be replaced by —O— or —CO—, and a compound represented by the formula (I-b): wherein R1 represents a C1-C20 monovalent saturated aliphatic hydrocarbon group in which one or more hydrogen atoms may be substituted with a hydroxyl group and one or more —CH2— may be replaced by —O— or —CO—, and n represents 0 or 1.Type: GrantFiled: March 29, 2012Date of Patent: September 30, 2014Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Ichikawa, Yukako Anryu, Satoshi Yamaguchi
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Patent number: 8846303Abstract: There is disclosed a resist top coat composition, used in a patterning process onto a photoresist film, wherein a resist top coat is formed by using the resist top coat composition onto a photoresist film formed on a wafer, and then, after exposure, removal of the resist top coat and development of the photoresist film are performed to effect the patterning on the photoresist film, wherein the resist top coat composition contains a truxene compound having phenol groups shown by the following general formula (1). As a result, there is provided a resist top coat composition not only having an effect from an environment to a resist film reduced and effectively shielding an OOB light, but also reducing film loss of a resist pattern and bridging between patterns and having an effect to enhance sensitivity of the resist; and a patterning process using this.Type: GrantFiled: September 25, 2012Date of Patent: September 30, 2014Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Jun Hatakeyama, Daisuke Kori
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Patent number: 8841061Abstract: A positive resist composition comprising a polymer having carboxyl groups substituted with an acid labile group having formula (1) exhibits a high contrast of alkaline dissolution rate before and after exposure, a high resolution, a reduced acid diffusion rate, and forms a pattern with good profile, minimal edge roughness, and etch resistance. In formula (1), R1 is methylene or ethylene, R2 is alkyl, aryl, or alkenyl, which may contain oxygen or sulfur, R3 is fluorine or trifluoromethyl, and m is an integer of 1 to 4.Type: GrantFiled: August 30, 2012Date of Patent: September 23, 2014Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Jun Hatakeyama, Koji Hasegawa
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Patent number: 8835097Abstract: There is disclosed a sulfonium salt shown by the following general formula (1). There can be a sulfonium salt capable of introducing an acid-generating unit generating an acid having an appropriate acid strength and not impairing adhesion with a substrate into a base polymer; a polymer using the said sulfonium salt; a chemically amplified resist composition using the said polymer as a base polymer; and a patterning process using the said chemically amplified resist composition.Type: GrantFiled: May 21, 2012Date of Patent: September 16, 2014Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Daisuke Domon, Keiichi Masunaga, Satoshi Watanabe
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Patent number: 8828645Abstract: There is disclosed a negative resist composition comprising at least: (A) a base polymer that is alkaline-soluble and is made alkaline-insoluble by action of an acid; (B) an acid generator; and (C) a basic component, wherein the base polymer at least contains a polymer including repeating units represented by the following general formula (1) and general formula (2) and having a weight average molecular weight of 1,000 to 10,000. There can be a negative resist composition hardly causing a bridge in forming a pattern and providing a high resolution and a patterning process using the same.Type: GrantFiled: October 25, 2013Date of Patent: September 9, 2014Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Akinobu Tanaka, Keiichi Masunaga, Daisuke Domon, Satoshi Watanabe
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Patent number: 8822136Abstract: A negative pattern is formed by coating a resist composition onto a substrate, the resist composition comprising a polymer comprising recurring units having an acid labile group-substituted hydroxyl group, an acid generator, an onium salt of perfluoroalkyl ether carboxylic acid, and an organic solvent, prebaking, exposing, baking, and developing in an organic solvent such that the unexposed region of film is dissolved away and the exposed region of film is not dissolved. In image formation via positive/negative reversal by organic solvent development, the resist film is characterized by a high dissolution contrast between the unexposed and exposed regions.Type: GrantFiled: October 26, 2012Date of Patent: September 2, 2014Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Jun Hatakeyama, Kazuhiro Katayama, Youichi Ohsawa
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Patent number: 8808959Abstract: 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) including a compound represented by (b1-1), a compound represented by (b1-1?) and/or a compound represented by (b1-1?) (R1?-R3? represents an aryl group or an alkyl group, provided that at least one of R1?-R3? represents a substituted aryl group being substituted with a group represented by (b1-1-0), and two of R1?-R3? may be mutually bonded to form a ring with the sulfur atom; X represents a C3-C30 hydrocarbon group; Q1 represents a carbonyl group-containing divalent linking group; X10 represents a C1-C30 hydrocarbon group; Q3 represents a single bond or a divalent linking group; Y10 represents —C(?O)— or —SO2—; Y11 represents a C1-C10 alkyl group or a fluorinated alkyl group: Q2 represents a single bond or an alkylene group; and W represents a C2-C10 alkylene group).Type: GrantFiled: November 10, 2009Date of Patent: August 19, 2014Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Hideo Hada, Yoshiyuki Utsumi, Takehiro Seshimo, Akiya Kawaue
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Patent number: 8808960Abstract: A compound represented by the formula (I): wherein R1 represents a hydrogen atom etc., R2 and R3 each independently represent a hydrogen atom etc., R4 represents a C1-C8 divalent hydrocarbon group, R5 represents a single bond etc., and R6 represents an unsubstituted or substituted C6-C20 aromatic hydrocarbon group, a polymer comprising a structural unit derived from the compound represented by the formula (I) and a chemically amplified positive resist composition comprising the polymer, at least one acid generator and at least one solvent.Type: GrantFiled: March 8, 2010Date of Patent: August 19, 2014Assignee: Sumitomo Chemical Company, LimitedInventors: Makoto Akita, Isao Yoshida, Kazuhiko Hashimoto
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Patent number: 8808966Abstract: A positive resist composition comprising a polymer having carboxyl groups substituted with an acid labile group having formula (1) exhibits a high contrast of alkaline dissolution rate before and after exposure, a high resolution, a good pattern profile and minimal edge roughness. In formula (1), A is —(CR22)m—, B is —(CR52)n—, R2 and R5 are hydrogen or alkyl, m and n are 1 or 2, R3 is alkyl, alkenyl, alkynyl or aryl, R6 is alkyl, alkoxy, alkanoyl, alkoxycarbonyl, hydroxyl, nitro, aryl, halogen, or cyano, and p is 0 to 4.Type: GrantFiled: July 25, 2012Date of Patent: August 19, 2014Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Jun Hatakeyama, Koji Hasegawa
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Patent number: 8802783Abstract: A photoresist material comprising a polymer with at least two acrylate derivatives incorporated therein, and a photo-acid generator for generating an acid by exposure, wherein at least one of the two acrylate derivatives incorporated therein comprises a norbornyl moiety having a lactone structure, and at least one of the two acrylate derivatives comprises an ester-substituted tetracyclododecyl moiety.Type: GrantFiled: November 28, 2012Date of Patent: August 12, 2014Assignee: NEC CorporationInventors: Katsumi Maeda, Shigeyuki Iwasa, Kaichiro Nakano, Etsuo Hasegawa
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Patent number: 8802349Abstract: Provided is an actinic ray-sensitive or radiation-sensitive resin composition including: (A) a resin capable of increasing the solubility in an alkali developer by the action of an acid, the resin containing (a) a repeating unit represented by the following formula (AN-01), (B) a compound capable of generating an acid upon irradiation with an actinic ray or radiation, and (C) a resin that contains at least either a fluorine atom or a silicon atom and contains a repeating unit having a group capable of decomposing by the action of an alkali developer to increase the solubility in an alkali developer: wherein the variables in formula (AN-01) are defined in the description.Type: GrantFiled: March 31, 2010Date of Patent: August 12, 2014Assignee: FUJIFILM CorporationInventors: Masahiro Yoshidome, Shuji Hirano, Hiroshi Saegusa, Kaoru Iwato, Yusuke Iizuka
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Patent number: 8802348Abstract: A radiation-sensitive resin composition includes (A) an acid labile group-containing resin which becomes alkali-soluble by an action of an acid, (B) a radiation-sensitive acid generator, and (C) a solvent. The resin (A) includes repeating units shown by formulas (1) and (2), wherein R1 and R2 represent a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, R3 represents a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, X represents a hydrogen atom, a hydroxyl group, or an acyl group, m represents an integer from 1 to 18, and n represents an integer from 4 to 8.Type: GrantFiled: February 7, 2010Date of Patent: August 12, 2014Assignee: JSR CorporationInventors: Noboru Otsuka, Takanori Kawakami, Yukio Nishimura, Makoto Sugiura
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Patent number: 8802347Abstract: Coating compositions include a polymer including: wherein R1 is a silicon containing moiety, R2 is an acid stable lactone functionality, and R3 is an acid labile lactone functionality; X1, X2, X3 are independently H or CH3; and m and o are non-zero positive integers and n is zero or a positive integer representing the number of repeat units; a photoacid generator; and a solvent. Also disclosed are methods for forming a pattern in the coating composition containing the same.Type: GrantFiled: November 6, 2009Date of Patent: August 12, 2014Assignee: International Business Machines CorporationInventors: Robert D. Allen, Phillip J. Brock, Kuang-Jung Chen, Alexander Friz, Wu-Song Huang, Ratnam Sooriyakumaran, Sally A. Swanson, Hoa D. Truong