Binder Containing Patents (Class 430/905)
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Patent number: 12178124Abstract: The invention relates to compounds that can be used in an organic electronic device as an active compound, in particular for use in electronic devices. The invention further relates to a method for producing the compounds according to the invention, and to electronic devices comprising same.Type: GrantFiled: September 24, 2019Date of Patent: December 24, 2024Assignee: Merck KGAAInventor: Philipp Stoessel
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Patent number: 12032290Abstract: According to the present invention, an actinic ray-sensitive or radiation-sensitive resin composition including a resin P having a repeating unit represented by General Formula (P1) and a compound that generates an acid having a pKa of ?1.40 or more upon irradiation with actinic rays or radiation; and a resist film, a pattern forming method, and a method for manufacturing an electronic device, each using the composition, are provided. Mp represents a single bond or a divalent linking group. Lp represents a divalent linking group. Xp represents O, S, or NRN1. RN1 represents a hydrogen atom or a monovalent organic group. Rp represents a monovalent organic group.Type: GrantFiled: June 11, 2021Date of Patent: July 9, 2024Assignee: FUJIFILM CorporationInventors: Daisuke Asakawa, Takashi Kawashima, Akiyoshi Goto, Michihiro Shirakawa, Kei Yamamoto
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Patent number: 12002674Abstract: Methods for making molecular sieves are provided. The molecular sieves are comprised of thin semiconductors films in which a plurality of apertures is defined. The apertures are non-circular, nanoscale openings with tapered sidewalls that selectively pass certain molecules, while discriminating against the passage of other molecules.Type: GrantFiled: April 11, 2019Date of Patent: June 4, 2024Assignee: WiSys Technology Foundation, Inc.Inventors: Gokul Gopalakrishnan, Mark Elliot Levenstein
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Patent number: 11976207Abstract: Water-based compositions containing a low VOC coalescent, a latex or water-dispersible polymer, and a water-insoluble UV-VIS (preferably, ultraviolet) absorber.Type: GrantFiled: March 28, 2022Date of Patent: May 7, 2024Assignee: SWIMC LLCInventors: Mary Jane Hibben, Mike Wildman, T. Howard Killilea, Iain Harvey
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Patent number: 11971660Abstract: A cross-linked polymer including a structure wherein at least a portion of phenolic hydroxyl groups in the polymer is protected by a group represented by the following formula (1): wherein R1 represents an alkyl group having 1 to 5 carbons and n represents an integer from 1 to 5; and * represents a bond part of the phenolic hydroxyl group to a residue other than a hydrogen atom, and a structure wherein at least a portion of phenolic hydroxyl groups in the polymer is protected by a group represented by the following formula (2): wherein R2 represents a divalent saturated hydrocarbon group having 2 to 17 carbons, containing an aromatic ring; and * represents a bond part of the phenolic hydroxyl group to a residue other than a hydrogen atom, and the polymers are cross-linked to each other.Type: GrantFiled: September 30, 2020Date of Patent: April 30, 2024Assignee: Maruzen Petrochemical Co., Ltd.Inventors: Tomohiro Masukawa, Masataka Nojima
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Patent number: 11966160Abstract: A radiation-sensitive resin composition includes: an onium salt compound represented by formula (1?); a resin including a structural unit having an acid-dissociable group; and a solvent. EA is a substituted or unsubstituted (?+?)-valent organic group having 1 to 40 carbon atoms; Z+ is a monovalent radiation-sensitive onium cation; and ? and ? are each independently 1 or 2.Type: GrantFiled: June 23, 2022Date of Patent: April 23, 2024Assignee: JSR CORPORATIONInventor: Ryuichi Nemoto
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Patent number: 11822240Abstract: A resist composition that generates an acid upon exposure and whose solubility in a developing solution is changed by action of an acid, the resist composition containing a base material component whose solubility in a developing solution is changed by action of an acid, and a compound represented by General Formula (e1) in which Rd01 represents a monovalent organic group and Rd02 represents a single bond or a divalent linking groupType: GrantFiled: December 14, 2020Date of Patent: November 21, 2023Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Yasuhiro Yoshii, Yosuke Suzuki, Yoichi Hori, Takahiro Kojima, Mari Murata
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Patent number: 11809082Abstract: A pattern forming method includes forming a resist film having a first region, a second region, and a third region, on a substrate, irradiating the first region with light or an energy ray in a first irradiation amount, and irradiating the second region with light or an energy ray in a second irradiation amount, the second irradiation amount being smaller than the first irradiation amount. The pattern forming method also includes dissolving the resist film of the first region by using first liquid, forming a coating film on a side surface of the resist film after the resist film of the first region is dissolved, and dissolving the third region by using second liquid that is different from the first liquid.Type: GrantFiled: March 2, 2021Date of Patent: November 7, 2023Assignee: KIOXIA CORPORATIONInventor: Mitsuru Kondo
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Patent number: 11768435Abstract: Materials and methods to immobilize photoacid generators on semiconducting substrates are provided. PAG-containing monomers are copolymerized with monomers to allow the polymer to bind to a surface, and optionally copolymerized with monomers to enhance solubility to generate PAG-containing polymers. The PAG-containing monomers can be coated onto a surface, where the immobilized PAGs can then be used to pattern materials coated on top of the immobilized PAGs, allowing direct patterning without the use of a photoresist, thereby reducing process steps and cost. The disclosed materials and processes can be used to produce conformal coatings of controlled thicknesses.Type: GrantFiled: November 1, 2019Date of Patent: September 26, 2023Assignee: Brewer Science, Inc.Inventors: Jinhua Dai, Joyce A. Lowes, Carissa Jones
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Patent number: 11762294Abstract: A photoresist underlayer composition, comprising a polymer comprising a repeating unit of formula (1): wherein Ar is a monocyclic or polycyclic C5-60 aromatic group, wherein the aromatic group comprises one or more aromatic ring heteroatoms, a substituent group comprising a heteroatom, or a combination thereof; R1 is hydrogen, substituted or unsubstituted C1-30 alkyl, substituted or unsubstituted C1-30 heteroalkyl, substituted or unsubstituted C3-30 cycloalkyl, substituted or unsubstituted C2-30 heterocycloalkyl, substituted or unsubstituted C2-30 alkenyl, substituted or unsubstituted C2-30 alkynyl, substituted or unsubstituted C6-30 aryl, substituted or unsubstituted C7-30 arylalkyl, substituted or unsubstituted C7-30 alkylaryl, substituted or unsubstituted C3-30 heteroaryl, or substituted or unsubstituted C4-30 heteroarylalkyl; and R2 is substituted or unsubstituted C1-30 alkyl, substituted or unsubstituted C1-30 heteroalkyl, substituted or unsubstituted C3-30 cycloalkyl, substituted or unsubstituted C2Type: GrantFiled: August 31, 2020Date of Patent: September 19, 2023Assignee: ROHM AND HAAS ELECTRONIC MATERIALS LLCInventors: Joshua Kaitz, Sheng Liu, Li Cui, Shintaro Yamada, Suzanne M. Coley, Iou-Sheng Ke
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Patent number: 11725078Abstract: [Problem to be Solved] To Provide a method for producing an acid-decomposable polymer having a reduced metal ion content, which suppresses decomposition and deprotection of the acid-decomposable polymer. [Means to Solve the Problem] The method for producing an acid-decomposable polymer according to the present invention comprises the steps of: preparing a polymer solution comprising an acid-decomposable polymer; washing an acidic cation exchanger with an organic solvent until the water content in the organic solvent discharged from the acidic cation exchanger falls to 400 ppm or less; and passing the polymer solution through the washed acidic cation exchanger to reduce the metal ion content of the polymer.Type: GrantFiled: June 5, 2020Date of Patent: August 15, 2023Assignee: Maruzen Petrochemical Co., Ltd.Inventors: Tomohiro Masukawa, Ryo Fujisawa
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Patent number: 11655329Abstract: Provided herein is a dual cure resin useful for the production of an object by additive manufacturing, comprising or consisting essentially of: (a) a photoinitiator; (b) not more than 5, 10 or 20 ppm of a polyurethane catalyst (e.g., tin, tertiary amine, bismuth, zinc, zirconium, or nickel catalysts); (c) a polyol; (d) free (i.e., unblocked) polyisocyanate; and (e) blocked polyisocyanate, the isocyanate groups of which are blocked by reaction with an amine (meth)acrylate blocking agent. Methods of making an object with the resin are also provided.Type: GrantFiled: April 19, 2021Date of Patent: May 23, 2023Assignee: Carbon, Inc.Inventor: Andrew Gordon Wright
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Patent number: 11500289Abstract: A positive resist composition comprising a base polymer comprising recurring units having a nitrogen-containing tertiary ester structure exhibits a high sensitivity, high resolution, low edge roughness (LER, LWR) and small size variation, and forms a pattern of good profile after exposure and development.Type: GrantFiled: December 10, 2019Date of Patent: November 15, 2022Assignee: SHIN-ETSU CHEMICAL CO., LTD.Inventor: Jun Hatakeyama
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Patent number: 10606212Abstract: The invention relates to a method for selecting compounds which can be used as additives in photopolymer formulations for producing light holographic media, and to photopolymer formulations which contain at least one softener which are selected according to the claimed method. The invention also relates to the use of photopolymer formulations for producing holographic media.Type: GrantFiled: March 29, 2017Date of Patent: March 31, 2020Assignee: Covestro Deutschland AGInventors: Thomas Roelle, Friedrich-Karl Bruder, Thomas Fäcke, Marc-Stephan Weiser, Dennis Hönel, Christian Diedrich
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Patent number: 9029070Abstract: There are provided a method of forming a resist pattern includes: a step (1) in which a resist composition containing a base component (A) that generates base upon exposure and exhibits increased solubility in an alkali developing solution by the action of acid is applied to a substrate to form a resist film; a step (2) in which the resist film 2 is subjected to exposure; a step (3) in which baking is conducted after the step (2); and a step (4) in which the resist film 2 is subjected to an alkali development, thereby forming a negative-tone resist pattern in which the unexposed portion 2b of the resist film 2 has been dissolved and removed, and the resist composition used in the step (1).Type: GrantFiled: November 2, 2012Date of Patent: May 12, 2015Assignee: Tokyo Ohka Kogyo Co., LtdInventors: Hiroaki Shimizu, Tsuyoshi Nakamura, Jiro Yokoya, Hideto Nito
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Patent number: 9017920Abstract: A film includes base and a photosensitive layer formed on the base. The photosensitive layer substantially includes a first photosensitive agent, a second photosensitive agent, and a thermosol. The first photosensitive agent is water-soluble. The second photosensitive agent is an aromatic ketone compound or a benzoin ether compound. The method for manufacturing the film and the masking method using the film is also provided.Type: GrantFiled: July 2, 2012Date of Patent: April 28, 2015Assignees: Shenzhen Futaihong Precision Industry Co., Ltd., FIH (Hong Kong) LimitedInventors: Quan Zhou, Chao-Sheng Huang, Xin-Wu Guan
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Patent number: 9005873Abstract: A method for producing a semiconductor device includes the steps of: applying a composition for forming a resist underlayer film for EUV lithography including a novolac resin containing a halogen atom onto a substrate having a film to be fabricated for forming a transferring pattern and baking the composition so as to form a resist underlayer film for EUV lithography; and applying a resist for EUV lithography onto the resist underlayer film for EUV lithography, irradiating, with EUV through a mask, the resist underlayer film for EUV lithography and a film of the resist for EUV lithography on the resist underlayer film, developing the film of the resist for EUV lithography, and transferring an image formed in the mask onto the substrate by dry etching so as to form an integrated circuit device.Type: GrantFiled: December 6, 2013Date of Patent: April 14, 2015Assignee: Nissan Chemical Industries, Ltd.Inventors: Rikimaru Sakamoto, Takafumi Endo, Bangching Ho
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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: 8993214Abstract: A positive photosensitive siloxane composition comprising at least three types of following polysiloxanes (A), (B) and (C) obtained by hydrolyzing and condensing a silane compound represented by general formula (1) R1nSi (OR2)4-n, a diazonaphthoquinone derivative, and a solvent: a polysiloxane (A) such that if pre-baked the film thereof will be soluble in a 5 weight % TMAH aqueous solution and the solution rate of said film will be 1,000 ?/sec or less; a polysiloxane (B) such that if pre-baked the solution rate of the film thereof will be 4,000 ?/sec or more relative to a 2.38 weight % TMAH aqueous solution; and a polysiloxane (C) such that if pre-baked the solution rate of the film thereof will be between 200 and 3,000 ?/sec relative to a 2.38 weight % TMAH aqueous solution.Type: GrantFiled: May 15, 2012Date of Patent: March 31, 2015Assignee: AZ Electronic Materials USA Corp.Inventors: Daishi Yokoyama, Takashi Fuke, Yuji Tashiro, Takashi Sekito, Toshiaki Nonaka
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Patent number: 8986923Abstract: Embodiments in accordance with the present invention encompass negative-tone, aqueous base developable, self-imagable polymer compositions useful for forming films that can be patterned to create structures for microelectronic devices, microelectronic packaging, microelectromechanical systems, optoelectronic devices and displays.Type: GrantFiled: October 10, 2013Date of Patent: March 24, 2015Assignee: Promerus, LLCInventors: Brian Knapp, Edmund Elce, Hendra Ng, Andrew Bell, Cheryl Burns, Sridevi Kaiti, Brian Kocher, Yogesh Patel, Masanobu Sakamoto, Xiaoming Wu, Wei Zhang
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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: 8968458Abstract: A composition for a resist underlayer film is provided. The composition has excellent storage stability and can form a resist underlayer film which has excellent adhesion to a resist film, can improve reproducibility of a resist pattern and is resistant to an alkaline liquid used in development and to oxygen asking during the removal of a resist. The composition comprises a hydrolyzate and/or a condensate of a silane compound of the following formula (A), R1bR2cSi(OR3)4-a??(A) wherein R1 is a monovalent organic group having at least one unsaturated bond, R2 individually represents a hydrogen atom, a halogen atom or a monovalent organic group, R3 individually represents a monovalent organic group, R1 is a group other than OR3, a is an integer of 1 to 3, b is an integer of 1 to 3, and c is an integer of 0 to 2, provided that a=b+c.Type: GrantFiled: March 2, 2010Date of Patent: March 3, 2015Assignee: JSR CorporationInventors: Keiji Konno, Masato Tanaka, Momoko Ishii, Junichi Takahashi, Tomoki Nagai
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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: 8916334Abstract: The present disclosure provides a micro-composite material used in the fabrication of three-dimensional objects, and associated methods and systems. In one example, a micro-composite material used in the fabrication of a three-dimensional object can comprise micronized polymeric particles; a photocurable curing agent; and a dye present in the micro-composite material in an amount at from 0.0001 wt % to 0.1 wt %, the dye having a ?max between 350 nm and 800 nm.Type: GrantFiled: January 28, 2013Date of Patent: December 23, 2014Assignee: Hewlett-Packard Development Company, L.P.Inventors: Sivapackia Ganapathiappan, Krzysztof Nauka, Hou T. Ng
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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: 8883398Abstract: The present application relates to a photoactive compound including an oxime ester group and a phosphonate group together, and a photosensitive resin composition comprising the same, the compound of the present application having excellent storage stability and high-temperature process characteristics.Type: GrantFiled: May 22, 2013Date of Patent: November 11, 2014Assignee: LG Chem, Ltd.Inventors: Changho Cho, Sunghyun Kim, Han Soo Kim, Sunhwa Kim, Raisa Kharbash, Jongho Park
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Patent number: 8883397Abstract: A positive photosensitive siloxane composition containing: a polysiloxane (Ia), which is obtained by hydrolyzing and condensing the silane compound represented by RSi(OR1)3 in general formula (1) and the silane compound represented by Si(OR1)4 in general formula (2) in the presence of a basic catalyst, and a pre-baked film of which has a dissolution rate of 1,000 ?/second or less in a 5 wt % TMAH aqueous solution; a polysiloxane (Ib), which is obtained by hydrolyzing and condensing at least the silane compound represented by general formula (1) in the presence of an acid or basic catalyst, and a pre-baked film of which has a dissolution rate of 100 ?/second or more in a 2.38 wt % TMAH aqueous solution; and a diazonaphthoquinone derivative and solvent.Type: GrantFiled: August 19, 2011Date of Patent: November 11, 2014Assignee: AZ Electronic Materials USA Corp.Inventors: Daishi Yokoyama, Takashi Fuke, Yuji Tashiro, Takashi Sekito, Toshiaki Nonaka
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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: 8871430Abstract: The present invention relates to a photoactive compound having a novel structure and a photosensitive resin composition including the same, and the photoactive compound according to the present invention has excellent sensitivity due to efficient absorption to a UV light source by including a nitro group and a phosphonate structure, and has excellent retention rate, mechanical strength, heat resistance, chemical resistance and developing resistance by improving solubility of the photosensitive resin composition by excellent compatibility of the phosphonate structure and a binder resin. Therefore, the photosensitive resin composition according to the present invention is useful to cure a column spacer, an overcoat, a passivation material and the like of a liquid crystal display device, and is useful in view of a high temperature process property.Type: GrantFiled: May 14, 2012Date of Patent: October 28, 2014Assignee: LG Chem, Ltd.Inventors: Changho Cho, Won Jin Chung, Raisa Kharbash, Sunghyun Kim, Dongchang Choi, Sang Chul Lee, Han Soo Kim, Yoon Hee Heo, Sunhwa Kim
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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: 8841060Abstract: An actinic-ray-sensitive or radiation-sensitive resin composition which is capable of improving line edge roughness (LER) and inhibiting pattern collapse, a resist film and a pattern forming method each using the same, a method for preparing an electronic device, and an electronic device are provided. The actinic-ray-sensitive or radiation-sensitive resin composition contains: (A) a resin having repeating units having a structure represented by any one of the following general formulae (I-1) to (I-3), and repeating units containing at least one selected from the group consisting of a lactone structure, a sultone structure, and a cyano group; and (B) a compound that generates an acid by irradiation with actinic rays or radiations.Type: GrantFiled: June 29, 2012Date of Patent: September 23, 2014Assignee: FUJIFILM CorporationInventors: Shohei Kataoka, Yusuke Iizuka, Akinori Shibuya, Tomoki Matsuda, Naohiro Tango
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Patent number: 8835098Abstract: Provided is a pattern forming method making it possible to obtain a pattern with less scums and watermark defects. The pattern forming method includes the steps of forming a film from an actinic-ray- or radiation-sensitive resin composition includes a resin (A) that exhibits an increased solubility in an alkali developer when acted on by an acid, a compound (B) that generates an acid when exposed to actinic rays or radiation, and a resin (C) containing at least one of a fluorine atom and a silicon atom, exposing the film to light, and developing the exposed film using a tetramethylammonium hydroxide solution whose concentration is less than 2.38 mass %.Type: GrantFiled: September 4, 2012Date of Patent: September 16, 2014Assignee: FUJIFILM CorporationInventor: Toshiaki Fukuhara
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Patent number: 8828643Abstract: A positive type resist composition for use in liquid immersion exposure comprises: (A) a resin having a monocyclic or polycyclic cycloaliphatic hydrocarbon structure, the resin increasing its solubility in an alkali developer by an action of acid; (B) a compound generating acid upon irradiation with one of an actinic ray and a radiation; (C) an alkali soluble compound having an alkyl group of 5 or more carbon atoms; and (D) a solvent.Type: GrantFiled: March 1, 2013Date of Patent: September 9, 2014Assignee: FUJIFILM CorporationInventors: Hiromi Kobayashi, Haruki Inabe
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Patent number: 8828282Abstract: Disclosed are a photosensitive resin composition for a color filter including (A) a colorant including a dye represented by the following Chemical Formula 1 and/or a dye represented by the following Chemical Formula 2, wherein in the following Chemical Formulae 1 and 2, each substituent is the same as described in the detailed description; (B) an acrylic-based binder resin; (C) a photopolymerizable monomer; (D) a photopolymerization initiator; and (E) a solvent, and a color filter using the same.Type: GrantFiled: September 30, 2013Date of Patent: September 9, 2014Assignee: Cheil Industries Inc.Inventors: Kyung-Hee Hyung, Nam-Gwang Kim, Se-Young Choi, Yu-Jin Lee, Gyu-Seok Han
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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: 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: 8808446Abstract: A composition for a resist underlayer film is provided. The composition has excellent storage stability and can form a resist underlayer film which has excellent adhesion to a resist film, can improve reproducibility of a resist pattern and is resistant to an alkaline liquid used in development and to oxygen ashing during the removal of a resist. The composition comprises a hydrolyzate and/or a condensate of a silane compound of the following formula (A), R1bR2cSi(OR3)4-a??(A) wherein R1 is a monovalent organic group having at least one unsaturated bond, R2 individually represents a hydrogen atom, a halogen atom or a monovalent organic group, R3 individually represents a monovalent organic group, R1 is a group other than OR3, a is an integer of 1 to 3, b is an integer of 1 to 3, and c is an integer of 0 to 2, provided that a=b+c.Type: GrantFiled: February 24, 2006Date of Patent: August 19, 2014Assignee: JSR CorporationInventors: Keiji Konno, Masato Tanaka, Momoko Ishii, Junichi Takahashi, Tomoki Nagai
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Patent number: 8802353Abstract: A radiation-sensitive composition containing 1 to 80% by weight of a solid component and 20 to 99% by weight of a solvent. The solid component contains a compound B which has (a) a structure derived from a polyphenol compound A by introducing an acid-dissociating group to at least one phenolic hydroxyl group of the polyphenol compound A which is synthesized by a condensation between a di- to tetrafunctional aromatic ketone or aromatic aldehyde each having 5 to 36 carbon atoms with a compound having 1 to 3 phenolic hydroxyl groups and 6 to 15 carbon atoms, and (b) a molecular weight of 400 to 2000. The composition containing the compound B is useful as an acid-amplified, non-polymeric resist material, because it is highly sensitive to radiation such as KrF excimer lasers, extreme ultraviolet rays, electron beams, and X-rays, and provides resist patterns with a high resolution, high heat resistance, and high etching resistance.Type: GrantFiled: September 13, 2012Date of Patent: August 12, 2014Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Masatoshi Echigo, Dai Oguro
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Patent number: 8795943Abstract: The present invention relates to a negative photoresist composition and a patterning method for device in which a photoresist pattern having a high sensitivity with a good reverse taper profile can be formed not only to realize an effective patterning of various thin films but also to facilitate removal of the photoresist pattern after the patterning. The photoresist composition comprises an alkali-soluble binder resin; a halogen-containing first photo-acid generator; a triazine-based second photo-acid generator; a cross-linking agent having an alkoxy structure; and a solvent.Type: GrantFiled: May 4, 2011Date of Patent: August 5, 2014Assignee: LG Chem, Ltd.Inventors: Chan-Hyo Park, Kyung-Jun Kim, Yu-Na Kim
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Patent number: 8795945Abstract: An actinic ray-sensitive or radiation-sensitive resin composition, and a resist film and a pattern forming method using the composition are provided, the composition including (A) a compound capable of decomposing by the action of an acid to increase the solubility of the resin (A) in an alkali developer; (B) a compound capable of generating an acid upon irradiation with an actinic ray or radiation; (C) a basic compound; and (D) a specific compound containing at least two specific alicyclic hydrocarbon groups each substituted with a hydroxyl group.Type: GrantFiled: March 4, 2011Date of Patent: August 5, 2014Assignee: FUJIFILM CorporationInventors: Kana Fujii, Takamitsu Tomiga, Toru Fujimori
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Patent number: 8790861Abstract: A monomer has the Formula I: wherein R1, R2, and R3 are each independently a C1-30 monovalent organic group, and R1, R2, and R3 are each independently unsubstituted or include a halogen, nitrile, ether, ester, ketone, alcohol, or a combination comprising at least one of the foregoing functional groups; R4 includes H, F, C1-4 alkyl, or C1-4 fluoroalkyl; A is a single bond or a divalent linker group, wherein A is unsubstituted or substituted to include a halogen, nitrile, ether, ester, ketone, alcohol, or a combination comprising at least one of the foregoing functional groups; m and n are each independently an integer of 1 to 8; and x is 0 to 2n+2, and y is 0 to 2m+2.Type: GrantFiled: December 21, 2012Date of Patent: July 29, 2014Assignee: Rohm and Haas Electronic Materials LLCInventors: Cong Liu, Mingqi Li, Cheng-Bai Xu
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Patent number: 8785105Abstract: A sulfonium salt having a 4-fluorophenyl group is introduced as recurring units into a polymer comprising hydroxyphenyl (meth)acrylate units and acid labile group-containing (meth)acrylate units to form a polymer which is useful as a base resin in a resist composition. The resist composition has a high sensitivity, high resolution and minimized LER.Type: GrantFiled: November 9, 2011Date of Patent: July 22, 2014Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Youichi Ohsawa, Masaki Ohashi, Seiichiro Tachibana, Jun Hatakeyama
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Patent number: 8778593Abstract: A chemical amplification resist composition contains: (A) a polymer compound having a phenolic hydroxyl group and a group formed by substituting a substituent for a hydrogen atom of a hydroxyl group in a phenolic hydroxyl group and satisfying the following (a) to (c) at the same time: (a) the polydispersity is 1.2 or less, (b) the weight average molecular weight is from 2,000 to 6,500, and (c) the glass transition temperature (Tg) is 140° C. or more.Type: GrantFiled: June 29, 2012Date of Patent: July 15, 2014Assignee: FUJIFILM CorporationInventors: Tomotaka Tsuchimura, Tadateru Yatsuo
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Patent number: 8778595Abstract: A resist composition containing a base component (A) which generates acid upon exposure, and exhibits changed solubility in a developing solution under the action of acid, wherein the base component (A) contains a polymeric compound (A1) having a structural unit (a5) represented by general formula (a5-0) shown below and a structural unit (a6) that generates acid upon exposure. In the formula, 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 sulfur atom or an oxygen atom, R2 represents a single bond or a divalent linking group, and Y represents a hydrocarbon group in which a carbon atom or a hydrogen atom may be substituted with a substituent.Type: GrantFiled: November 16, 2012Date of Patent: July 15, 2014Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Daichi Takaki, Daiju Shiono, Yoshiyuki Utsumi, Jun Iwashita
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Patent number: 8765358Abstract: A water-soluble resin composition for forming fine patterns comprising water-soluble polymer represented by Chemical Formula 1 as below and the first water-soluble solvent, is coated and heated on a photoresist layer having at least one contact hole to reduce a size of the at least one contact hole. (In Chemical Formula 1, each of R1, R2, R3 and R5 independently represents an alkyl group of C1-30 or an cyclo alkyl group of C3-30 which respectively have one selected from the group consisting of hydrogen, an ether group, an ester group, a carbonyl group, an acetal, an epoxy group, a nitril group, an amine group, and an aldehyde group; each of R4, R6, R7 and R8 independently represents hydrogen or a methyl group; n represents an integer of 0 to 5; a represents a real number of 0.05 to 0.5; each of b, c and d respectively represents a real number of 0 to 0.7; and a+b+c+d=1).Type: GrantFiled: June 29, 2011Date of Patent: July 1, 2014Assignee: Korea Kumho Petrochemical Co., Ltd.Inventors: Sang Wook Park, So Jung Park, Dong-Chul Seo
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Patent number: 8765353Abstract: A resist composition includes: a crosslinking material that is crosslinked in the presence of an acid; an acid amplifier; and a solvent.Type: GrantFiled: September 21, 2011Date of Patent: July 1, 2014Assignee: Sony CorporationInventors: Koji Arimitsu, Nobuyuki Matsuzawa, Isao Mita
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Patent number: 8758974Abstract: A method is described for the direct photochemical modification and micro-patterning of polymer surfaces, without the need to use a photoresist. For example, micropatterns of various functional chemical groups, biomolecules, and metal films have been deposited on poly(carbonate) and poly(methyl methacrylate) surfaces. These patterns may be used, for example, in integrated electronics, capture elements, or sensing elements in micro-fluidic channels.Type: GrantFiled: December 12, 2003Date of Patent: June 24, 2014Assignee: Board of Supervisors of Louisiana State University And Agricultural and Mechanical CollegeInventors: Steven A. Soper, Robin L. McCarley, Bikas Vaidya
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Patent number: 8748078Abstract: A cyclic compound represented by formula (1): wherein L, R1, R?, and m are as defined in the specification. The cyclic compound of formula (1) is highly soluble to a safety solvent, highly sensitive, and capable of forming resist patterns with good profile. Therefore, the cyclic compound is useful as a component of a radiation-sensitive composition.Type: GrantFiled: August 30, 2010Date of Patent: June 10, 2014Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Hiromi Hayashi, Masatoshi Echigo, Dai Oguro
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Patent number: 8735048Abstract: An actinic ray-sensitive or radiation-sensitive resin composition comprising (P) a resin having a repeating unit represented by the following formula (1), a resist film using the composition, and a pattern forming method.Type: GrantFiled: January 27, 2011Date of Patent: May 27, 2014Assignee: FUJIFILM CorporationInventors: Takeshi Inasaki, Takayuki Ito, Tomotaka Tsuchimura, Tadateru Yatsuo, Koutarou Takahashi
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Patent number: 8735044Abstract: A salt represented by the formula (a): wherein Q1 and Q2 each independently represent a fluorine atom etc., X1 represents a single bond etc., X2 represents a single bond etc., Y1 represents a C3-C6 alicyclic hydrocarbon group etc., with the proviso that —X2—Y1 group has one or more fluorine atoms, and Z+ represents an organic counter cation, and a photoresist composition comprising the salt represented by the formula (a) and a resin comprising a structural unit having an acid-labile group and being insoluble or poorly soluble in an aqueous alkali solution but becoming soluble in an aqueous alkali solution by the action of an acid.Type: GrantFiled: May 25, 2010Date of Patent: May 27, 2014Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Ichikawa, Isao Yoshida