Pattern Elevated In Radiation Unexposed Areas Patents (Class 430/326)
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Patent number: 11067890Abstract: An actinic ray-sensitive or radiation-sensitive resin composition contains a compound represented by General Formula (1). In General Formula (1), X represents a sulfur atom or an iodine atom. m represents 1 or 2, in a case where X is a sulfur atom, m is 2, and in a case where X is an iodine atom, m is 1. R1's each independently represent an alkyl group or alkenyl group which may include a heteroatom, an aromatic heterocyclic group, or an aromatic hydrocarbon ring group. Further, in a case where m is 2, two R1's may be bonded to each other to form a ring. R2 represents a divalent linking group. R3 represents a divalent linking group having no aromatic group. Y? represents an anionic moiety. The pKa of the compound represented by General Formula (1) as Y? is protonated is ?2.0 to 1.5.Type: GrantFiled: July 10, 2019Date of Patent: July 20, 2021Assignee: FUJIFILM CorporationInventors: Akiyoshi Goto, Masafumi Kojima, Akira Takada, Keita Kato, Kyohei Sakita
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Patent number: 10264785Abstract: New stabilizers for solutions of choline hydroxide and related quaternary trialkylalkanolamines are disclosed. The stabilizers are alkyl hydroxylamines, hydrazines, hydrazides, or derivates thereof, including compounds containing more than one such functionality. The new stabilizers are effective at concentrations less than about 1000 ppm, and choline hydroxide solutions stabilized with the compounds described herein typically have Gardner Color change less than about 2.0 after six months at reasonable temperatures.Type: GrantFiled: May 1, 2017Date of Patent: April 23, 2019Assignee: HUNTSMAN PETROCHEMICAL LLCInventor: Dave C Ferguson
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Patent number: 10083832Abstract: Under layer composition and methods of manufacturing semiconductor devices are disclosed. The method of manufacturing semiconductor device includes the following steps. A layer of an under layer composition is formed, wherein the under layer composition includes a polymeric material and a cross-linker, and the cross-linker includes at least one decomposable functional group. A curing process is performed on the layer of the under layer composition to form an under layer, wherein the cross-linker is crosslinked with the polymeric material to form a crosslinked polymeric material having the at least one decomposable functional group. A patterned photoresist layer is formed over the under layer. An etching process is performed to transfer a pattern of the patterned photoresist layer to the under layer. The under layer is removed by decomposing the decomposable functional group.Type: GrantFiled: March 24, 2017Date of Patent: September 25, 2018Assignee: Taiwan Semiconductor Manufacturing Co., Ltd.Inventors: Chen-Yu Liu, Chin-Hsiang Lin, Ching-Yu Chang, Ming-Hui Weng
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Patent number: 10007179Abstract: Provided are ionic thermal acid generators comprising an anion of an aromatic sulfonic acid comprising one or more fluorinated alcohol group and a cation. Also provided are photoresist pattern trimming compositions that include an ionic thermal acid generator, a matrix polymer and a solvent, and methods of trimming a photoresist pattern using the trimming compositions. The thermal acid generators, compositions and methods find particular applicability in the manufacture of semiconductor devices.Type: GrantFiled: October 19, 2016Date of Patent: June 26, 2018Assignee: Rohm and Haas Electronic Materials LLCInventors: Irvinder Kaur, Cong Liu, Kevin Rowell, Gerhard Pohlers, Mingqi Li
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Patent number: 9926462Abstract: An immersion upper layer film-forming composition includes [A] a polymer component that includes a polymer (A1), and [B] a solvent, the polymer (A1) including a structural unit (I) that includes a group represented by the following formula (i). The structural unit (I) is preferably a structural unit (I-1) represented by the following formula (1). The polymer component [A] preferably further includes a structural unit (II-1) represented by the following formula (2), the structural unit (II-1) being included in the polymer (A1) or a polymer other than the polymer (A1). The polymer component [A] preferably further includes a structural unit (III) that includes a carboxyl group, the structural unit (III) being included in the polymer (A1) or a polymer other than the polymer (A1).Type: GrantFiled: November 22, 2016Date of Patent: March 27, 2018Assignee: JSR CORPORATIONInventors: Kiyoshi Tanaka, Kazunori Kusabiraki, Takahiro Hayama, Motoyuki Shima
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Patent number: 9696629Abstract: Photoresist pattern trimming compositions are provided. The compositions comprise: a matrix polymer, an aromatic sulfonic acid and a solvent, wherein the aromatic sulfonic acid comprises one or more fluorinated alcohol group. Also provided are methods of trimming a photoresist pattern using the trimming compositions. The compositions and methods find particular applicability in the manufacture of semiconductor devices.Type: GrantFiled: December 16, 2015Date of Patent: July 4, 2017Assignee: Rohm and Haas Electronic Materials LLCInventors: Irvinder Kaur, Cong Liu, Kevin Rowell
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Patent number: 9653293Abstract: A manufacturing a semiconductor device of the present disclosure includes coating a photosensitive material on a workpiece; exposing the photosensitive material using a first exposure mask; performing a positive-tone development on the photosensitive material using a first developer after the first exposing; exposing the photosensitive material using a second exposure mask after the first developing; and performing a negative-tone development on the photosensitive material using a second developer after the second exposing.Type: GrantFiled: February 11, 2015Date of Patent: May 16, 2017Assignee: TOKYO ELECTRON LIMITEDInventor: Hidetami Yaegashi
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Patent number: 9645494Abstract: There is provided a resist underlayer film forming composition that is used in a lithography process for the production of semiconductor devices and that can be developed with an alkaline developer for photoresists, and a method of forming a photoresist pattern by using the resist underlayer film forming composition. The resist underlayer film forming composition used in a lithography process for a production of a semiconductor device comprising: an alkali-soluble resin (a); a polynuclear phenol (b); a compound (c) having at least two vinylether groups; and a photoacid generator (d). The alkali-soluble resin (a) may be a polymer containing a unit structure having a carboxyl group, and the polynuclear phenol (b) may be a compound having 2 to 30 phenolic hydroxyl groups in the molecule.Type: GrantFiled: December 11, 2007Date of Patent: May 9, 2017Assignee: NISSAN CHEMICAL INDUSTRIES, LTD.Inventors: Masakazu Kato, Takahiro Hamada, Tomoyuki Enomoto
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Patent number: 9540535Abstract: An immersion upper layer film-forming composition includes [A] a polymer component that includes a polymer (A1), and [B] a solvent, the polymer (A1) including a structural unit (I) that includes a group represented by the following formula (i). The structural unit (I) is preferably a structural unit (I-1) represented by the following formula (1). The polymer component [A] preferably further includes a structural unit (II-1) represented by the following formula (2), the structural unit (II-1) being included in the polymer (A1) or a polymer other than the polymer (A1). The polymer component [A] preferably further includes a structural unit (III) that includes a carboxyl group, the structural unit (III) being included in the polymer (A1) or a polymer other than the polymer (A1).Type: GrantFiled: March 28, 2013Date of Patent: January 10, 2017Assignee: JSR CORPORATIONInventors: Kiyoshi Tanaka, Kazunori Kusabiraki, Takahiro Hayama, Motoyuki Shima
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Patent number: 9529266Abstract: Using a resist composition which exhibits decreased solubility in an organic solvent upon exposure, patterning is conducted by a negative-tone development using a developing solution containing an organic solvent to form a first resist pattern on the substrate, wherein the first resist pattern is composed of a plurality of exposed portions. Then, a pattern reversing composition containing an organic solvent which does not dissolve the first resist pattern is applied to the substrate on which the first resist pattern has been formed, to form a pattern reversing film. Next, the first resist pattern is removed and patterning of the pattern reversing film is conducted by an alkali developing to form a reversed pattern in which the image of the first resist pattern is reversed.Type: GrantFiled: December 22, 2014Date of Patent: December 27, 2016Assignee: TOKYO OHKA KOGYO CO., LTD.Inventors: Tomohiro Oikawa, Kazuishi Tanno
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Patent number: 9519217Abstract: A chemically amplified positive resist composition is provided comprising a substantially alkali-insoluble polymer having an acid labile group-protected acidic functional group, a poly(meth)acrylate polymer having Mw of 1,000-500,000, and an acid generator in a solvent. The composition forms on a substrate a resist film of 5-100 ?m thick which can be briefly developed to form a pattern at a high sensitivity and a high degree of removal or dissolution to bottom.Type: GrantFiled: June 5, 2015Date of Patent: December 13, 2016Assignee: SHIN-ETSU CHEMICAL CO., LTD.Inventors: Katsuya Takemura, Yoshinori Hirano
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Patent number: 9448482Abstract: There is provided a pattern forming method including (1) forming a film by an actinic ray-sensitive or radiation-sensitive resin composition containing a resin (A) capable of increasing the polarity by the action of an acid so that a solubility thereof in a developer containing an organic solvent is decreased, (2) exposing the film, (3) developing the film by a developer including an organic solvent to form a negative pattern having a space part obtained by removing a part of the film and a residual film part which is not removed by the developing, (4) forming a resist film for reversing a pattern, on the negative pattern, so as to be embedded in the space part in the negative pattern, and (5) reversing the negative pattern into a positive pattern by removing the residual film part in the negative pattern by using an alkaline wet etching liquid.Type: GrantFiled: May 22, 2015Date of Patent: September 20, 2016Assignee: FUJIFILM CorporationInventors: Kaoru Iwato, Takanobu Takeda, Hiroo Takizawa
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Patent number: 9399076Abstract: A sensor for the in vivo detection of glucose comprises: components of an assay for glucose, a readout of which is a detectable optical signal which can be interrogated transcutaneously by external optical means when the sensor is implanted in vivo; and a shell of biodegradable material encapsulating the assay components while allowing analyte to contact the assay components, wherein the biodegradable material comprises a co-polymer having hydrophobic and hydrophilic units. A method of preparing such a sensor preferably comprises coacervation, solvent evaporation and/or extraction, spray drying, spray coating, spray chilling, rotary disk atomisation, fluid bed coating, coextrusion and/or pan coating. A method of detecting glucose using such a sensor suitably comprises implantation of the sensor into the skin of a mammal, transdermal detection or measurement of glucose using external optical means and degradation of the biodegradable material.Type: GrantFiled: May 17, 2005Date of Patent: July 26, 2016Assignee: MEDTRONIC MINIMED, INC.Inventors: Yihua Yu, Jesper S. Kristensen
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Patent number: 9401450Abstract: Methods of fabricating solar cell emitter regions using ion implantation, and resulting solar cells, are described. In an example, a method of fabricating alternating N-type and P-type emitter regions of a solar cell involves forming a silicon layer above a substrate. Dopant impurity atoms of a first conductivity type are implanted, through a first shadow mask, in the silicon layer to form first implanted regions and resulting in non-implanted regions of the silicon layer. Dopant impurity atoms of a second, opposite, conductivity type are implanted, through a second shadow mask, in portions of the non-implanted regions of the silicon layer to form second implanted regions and resulting in remaining non-implanted regions of the silicon layer. The remaining non-implanted regions of the silicon layer are removed with a selective etch process, while the first and second implanted regions of the silicon layer are annealed to form doped polycrystalline silicon emitter regions.Type: GrantFiled: December 5, 2014Date of Patent: July 26, 2016Assignee: SunPower CorporationInventors: Timothy Weidman, David D. Smith
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Patent number: 9316908Abstract: Provided is an actinic-ray- or radiation-sensitive resin composition including (A) a resin that when acted on by an acid, is decomposed to thereby increase its alkali solubility, which resin comprises at least either any of repeating units (I) of general formula (I) below or any of repeating units (II) of general formula (II) below, (B) an onium salt acid generator that when exposed to actinic rays or radiation, generates a sulfonic acid whose volume ranges from 250 ?3 to less than 350 ?3, and (C) an onium salt acid generator that when exposed to actinic rays or radiation, generates a sulfonic acid whose volume is 400 ?3 or greater.Type: GrantFiled: August 29, 2014Date of Patent: April 19, 2016Assignee: FUJIFILM CorporationInventor: Koutarou Takahashi
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Patent number: 9280052Abstract: The present invention includes: a resist film forming step of forming a resist film over a substrate; an exposure step of exposing the resist film into a predetermined pattern; a metal treatment step of causing a treatment agent to enter an exposed portion exposed in the exposure step of the resist film and causing metal to infiltrate the exposed portion via the treatment agent; and a resist film removing step of removing an unexposed portion not exposed in the exposure step of the resist film to form a resist pattern over the substrate.Type: GrantFiled: February 11, 2014Date of Patent: March 8, 2016Assignee: Tokyo Electron LimitedInventors: Fumiko Iwao, Satoru Shimura
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Patent number: 9184057Abstract: A method for manufacturing integrated circuit devices, optical devices, micromachines and mechanical precision devices, the said method comprising the steps of (1) providing a substrate having patterned material layers having line-space dimensions of 50 nm and less and aspect ratios of >2; (2) providing the surface of the patterned material layers with a positive or a negative electrical charge by contacting the substrate at least once with an aqueous, fluorine-free solution S containing at least one fluorine-free cationic surfactant A having at least one cationic or potentially cationic group, at least one fluorine-free anionic surfactant A having at least one anionic or potentially anionic group, or at least one fluorine-free amphoteric surfactant A; and (3) removing the aqueous, fluorine-free solution S from the contact with the substrate.Type: GrantFiled: February 29, 2012Date of Patent: November 10, 2015Assignee: BASF SEInventors: Andreas Klipp, Guenter Oetter, Sabrina Montero Pancera, Andrei Honciuc, Christian Bittner
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Patent number: 9170488Abstract: A resist pattern-forming method includes coating a radiation-sensitive resin composition on a substrate to provide a resist film. The resist film is exposed. The exposed resist film is developed using a developer solution including no less than 80% by mass of an organic solvent. The radiation-sensitive resin composition includes a polymer, a radiation-sensitive acid generator, and an acid diffusion controller which includes a compound having an amide group. The polymer has a weight average molecular weight in terms of the polystyrene equivalent of greater than 6,000 and includes a first structural unit that includes an acid-labile group. The polymer includes less than 5 mol % or 0 mol % of a second structural unit that includes a hydroxyl group.Type: GrantFiled: June 17, 2014Date of Patent: October 27, 2015Assignee: JSR CORPORATIONInventors: Hirokazu Sakakibara, Taiichi Furukawa, Reiko Kimura, Masafumi Hori
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Patent number: 9164384Abstract: A negative pattern is formed by coating a resist composition comprising a polymer comprising recurring units of formulae (1) and (2) and a photoacid generator of formula (3) onto a substrate, baking, exposure, PEB and developing in an organic solvent. In formulae (1) and (2), R1 is H, F, CH3 or CF3, Z is a single bond, phenylene, naphthylene, or (backbone)-C(?O)—O—Z?—, Z? is alkylene, phenylene or naphthylene, XA is an acid labile group, YL is H or a polar group. In formula (3), R2 and R3 are a monovalent hydrocarbon group, R4 is a divalent hydrocarbon group, or R2 and R3, or R2 and R4 may form a ring with the sulfur, L is a single bond or a divalent hydrocarbon group, Xa and Xb are H, F or CF3, and k is an integer of 1 to 4.Type: GrantFiled: April 10, 2014Date of Patent: October 20, 2015Assignee: SHIN-ETSU CHEMICAL CO., LTD.Inventors: Masaki Ohashi, Masahiro Fukushima, Tomohiro Kobayashi, Kazuhiro Katayama, Chuanwen Lin
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Patent number: 9122147Abstract: A pattern is formed by coating a resist composition comprising a resin comprising recurring units having an acid labile group, a photoacid generator, and a first organic solvent onto a processable substrate, prebaking, exposing, PEB, and developing in an organic solvent developer to form a negative pattern; heating the negative pattern to render it resistant to a second organic solvent; coating a solution of a resin having a carbon content of at least 75 wt % in the second organic solvent thereon, prebaking, and dry etching to effect image reversal for converting the negative pattern into a positive pattern.Type: GrantFiled: January 16, 2014Date of Patent: September 1, 2015Assignee: SHIN-ESTU CHEMICAL CO., LTD.Inventors: Jun Hatakeyama, Tsutomu Ogihara
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Patent number: 9116437Abstract: A pattern forming method, including: (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 a developer containing an organic solvent, wherein the chemical amplification resist composition contains: (A) a resin capable of decreasing a solubility of the resin (A) in the developer containing an organic solvent by an action of an acid; (B) a compound capable of generating an acid upon irradiation with an actinic ray or radiation; and (C) a basic, compound or ammonium salt compound whose basicity decreases upon irradiation with an actinic ray or radiation, and a resist composition used for the pattern forming method and a resist film formed from the resist composition are provided.Type: GrantFiled: June 14, 2010Date of Patent: August 25, 2015Assignee: FUJIFILM CorporationInventors: Yuichiro Enomoto, Sou Kamimura, Shinji Tarutani
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Patent number: 9104107Abstract: DUV lithography process that eliminates post exposure baking of a photoresist. Thick photoresist may be processed to obtain enhanced sidewall profiles for microelectronic devices.Type: GrantFiled: May 29, 2013Date of Patent: August 11, 2015Assignee: Western Digital (Fremont), LLCInventors: Xianzhong Zeng, Hai Sun
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Patent number: 9080018Abstract: The present invention provides a polydialkylsilane, and a method for producing a polydialkylsilane, including a step of adding a compound represented by formula (I) (in formula (I), R1 and R2 independently represent an alkyl group, and X1 and X2 independently represent a halogen atom) to an organic solvent containing an alkali metal, in which 0.010 [hr?1]?the average addition rate of compound (I) [moles·hr?1]/the amount of the alkali metal [moles]?0.055 [hr?1].Type: GrantFiled: February 27, 2013Date of Patent: July 14, 2015Assignee: NIPPON SODA CO., LTD.Inventors: Kenichi Hayashi, Masamichi Yasuhara, Makoto Toyooka, Hideki Maekawa
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Patent number: 9052603Abstract: A pattern is formed by coating a chemically amplified resist composition comprising a resin having a dissolution rate in an organic solvent developer that lowers under the action of acid onto a processable substrate, prebaking, exposing the resist film, PEB, developing in an organic solvent developer to form a negative pattern, coating a solution comprising Si, Ti, Zr, Hf or Al, prebaking, and dry etching to effect image reversal for converting the negative pattern into a positive pattern.Type: GrantFiled: January 31, 2014Date of Patent: June 9, 2015Assignee: SHIN-ETSU CHEMICAL CO., LTD.Inventors: Jun Hatakeyama, Tsutomu Ogihara, Yusuke Biyajima
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Publication number: 20150147697Abstract: A resist composition comprising a polymer comprising recurring units (a) of formula (1) and having a Mw of 1,000-500,000 as base resin is provided. R1 is H or methyl, X is a single bond or —C(?O)—O—R5—, R2 is a single bond or C1-C4 alkylene, R3 is C2-C8 alkylene, R4 is an acid labile group, R5 is a single bond or C1-C4 alkylene, and 0<a?1.0. The composition is of dual-tone type in that an intermediate dose region of resist film is dissolved in a developer, but unexposed and over-exposed regions of resist film are insoluble.Type: ApplicationFiled: November 25, 2014Publication date: May 28, 2015Applicant: SHIN-ETSU CHEMICAL CO., LTD.Inventors: Jun Hatakeyama, Masayoshi Sagehashi
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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: 9034557Abstract: A photoresist composition. The composition has the following: (a) one or more resin binders that include one or more acid sensitive groups and that are substantially free of phenolic groups protected by acetal or ketal groups; (b) one or more photo acid generators, that, upon exposure to a source of high energy, decompose and generate a photoacid strong enough to remove the one or more acid sensitive groups; (c) one or more ionic non-photosensitive additives including an iminium salt; and (d) one or more solvents. There is also a process for patterning relief structures on a substrate employing the photoresist composition.Type: GrantFiled: June 1, 2010Date of Patent: May 19, 2015Assignee: FUJIFILM ELECTRONIC MATERIALS U.S.A., INC.Inventors: Ognian N. Dimov, Binod B. De
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Patent number: 9034558Abstract: Provided is an actinic-ray- or radiation-sensitive resin composition including (A) a compound that when exposed to actinic rays or radiation, generates an acid, (B) a resin that when acted on by an acid, increases its rate of dissolution in an alkali developer, and (C) a hydrophobic resin, wherein the hydrophobic resin (C) contains a repeating unit derived from any of monomers of general formula (1) below.Type: GrantFiled: September 28, 2011Date of Patent: May 19, 2015Assignee: FUJIFILM CorporationInventors: Shuhei Yamaguchi, Akinori Shibuya, Yusuke Iizuka
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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: 9029075Abstract: A pattern is printed by forming a photoresist layer on a wafer, forming a protective film thereon, exposure, and development. The protective film is formed from a composition comprising a copolymer of hydroxystyrene with acenaphthylene and/or vinylnaphthalene and a mixture of an alcohol solvent and an ether or aromatic solvent.Type: GrantFiled: December 6, 2012Date of Patent: May 12, 2015Assignee: Shin-Etsu Chemical Co., Ltd.Inventor: Jun Hatakeyama
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Patent number: 9029062Abstract: A method and photoresist material for the patterning of integrated circuit (IC) components using ultra violet (UV) and extreme ultraviolet lithography (EUV) that includes providing a substrate, forming a first material layer over the substrate, forming a second material layer over the first material layer, the second material layer having a luminescent agent, and exposing one or more portions of the second material layer.Type: GrantFiled: June 30, 2010Date of Patent: May 12, 2015Assignee: Taiwan Semiconductor Manufacturing Company, Ltd.Inventors: Chien-Wei Wang, Chun-Ching Huang
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Patent number: 9023585Abstract: A resist composition which generates a base upon exposure and exhibits increased solubility in an alkali developing solution under the action of acid, and the resist composition including: a base component (A) that exhibits increased solubility in an alkali developing solution under the action of acid; an acidic compound component (G1) including a nitrogen-containing cation having a pKa value of 7 or less and a counteranion; and a buffer component (K) including a nitrogen-containing cation and a counteranion being a conjugate base for the acid having a pKa value of 0 to 5.Type: GrantFiled: June 20, 2013Date of Patent: May 5, 2015Assignee: Tokyo Ohka Kogyo Co., LtdInventors: Tsuyoshi Nakamura, Jiro Yokoya, Hideto Nito, Hiroaki Shimizu
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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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Publication number: 20150118621Abstract: Provided is a method of forming a pattern, including (a) forming a film comprising an actinic-ray- or radiation-sensitive resin composition comprising a resin (P) containing a repeating unit (P1) with a cyclic carbonic acid ester structure and any of repeating units (P2) of general formula (P2-1) below, and a compound (B) that when exposed to actinic rays or radiation, generates an acid, (b) exposing the film to actinic rays or radiation, and (c) developing the exposed film with a developer comprising an organic solvent to thereby obtain a negative pattern.Type: ApplicationFiled: January 2, 2015Publication date: April 30, 2015Applicant: FUJIFILM CorporationInventors: Toshiaki FUKUHARA, Kaoru IWATO
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Patent number: 9017905Abstract: In a chemically amplified positive resist composition comprising (A) a base resin, (B) a photoacid generator, (C) a thermal crosslinker, and (D) an organic solvent, the base resin is a specific polymer and the crosslinker is a siloxane compound. A coating of the composition is readily developable in aqueous alkaline solution. On heat treatment, it forms a cured resist pattern film of satisfactory profile.Type: GrantFiled: September 23, 2013Date of Patent: April 28, 2015Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Masashi Iio, Katsuya Takemura, Takashi Miyazaki, Hideyoshi Yanagisawa
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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: 9012126Abstract: The invention relates to a novel positive working photosensitive composition having: at least one photoacid generator; at least one novolak polymer; at least one polymer, having a polymer backbone, said polymer comprising a structure of the following formula: wherein R1-R5 are, independently, —H or —CH3, A is a linear or branched C1-C10 alkylene group, B is a C1-C12 alkyl or alicyclic group, D is a linking group that may be a chemical bond, a carboxylate group, wherein the carbonyl carbon is bonded to the polymer backbone, or a —COOCH2— group, wherein the carbonyl carbon is bonded to the polymer backbone, Ar is a substituted or unsubstituted aromatic group or heteroaromatic group, E is a linear or branched C2-C10 alkylene group, G is an acid cleavable group. The invention further relates to a process for using the novel composition for forming an image.Type: GrantFiled: June 15, 2012Date of Patent: April 21, 2015Assignee: AZ Electronic Materials (Luxembourg) S.A.R.L.Inventors: Weihong Liu, PingHung Lu, Chunwei Chen, Stephen Meyer, Medhat Toukhy, SookMee Lai
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Patent number: 9005872Abstract: A resist composition including a base component (A) which exhibits changed solubility in a developing solution under action of acid, a basic-compound component (C) and an acid-generator component (B) which generates acid upon exposure, the component (B) including a compound represented by formula (b1), and the component (C) including at least one compound represented by formulas (c1) to (c3) (wherein Z1 represents a ring skeleton-containing hydrocarbon group, Q1 represents a divalent linking group containing oxygen, Y1 represents a fluorinated alkylene group, M+ represents an organic cation, R1 represents a fluorinated alkyl group or a hydrocarbon group, L1+ and L2+ represents a sulfonium or an iodonium, Z2 represents a hydrogen atom or a hydrocarbon group, Y2 represents a single bond or a divalent linking group containing no fluorine, R2 represents an organic group, Y3 represents an alkylene group or an arylene group; and Rf represents a fluorine-containing hydrocarbon group).Type: GrantFiled: February 16, 2012Date of Patent: April 14, 2015Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Hiroaki Shimizu, Sho Abe, Hideto Nito
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Patent number: 9005871Abstract: Compounds of the formula (I), wherein Ar1 is for example phenylene or biphenylene both unsubstituted or substituted; Ar2 and Ar3 are for example independently of each other phenyl, naphthyl, biphenylylyl or heteroaryl, all optionally substituted; or Ar1 and Ar2 for example together with a direct bond, O, S or (CO), form a fused ring system; R is for example hydrogen, C3-C30cycloalkyl or C1-C18alkyl; and R1, R2 and R3 independently of each other are for example C1-C10haloalkyl; are effective photoacid generators (PAG).Type: GrantFiled: October 8, 2009Date of Patent: April 14, 2015Assignee: BASF SEInventors: Hitoshi Yamato, Toshikage Asakura, Yuichi Nishimae
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Patent number: 9005880Abstract: New photoresist compositions are provided that are useful for immersion lithography. Preferred photoresist compositions of the invention comprise one or more materials that have sulfonamide substitution. Particularly preferred photoresists of the invention can exhibit reduced leaching of resist materials into an immersion fluid contacting the resist layer during immersion lithography processing.Type: GrantFiled: November 19, 2009Date of Patent: April 14, 2015Assignee: Rohm and Haas Electronic Materials, LLCInventors: Deyan Wang, Chunyi Wu, George G. Barclay, Cheng-Bai Xu
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Patent number: 9005874Abstract: There are provided a novel compound, a polymeric compound, a resist composition, an acid generator and a method of forming a resist pattern the compound represented by general formula (1-1): wherein each of R1 and R3 independently represents a single bond or a divalent linking group; A represents a divalent linking group; each of R2 and R4 independently represents a hydroxyl group, a hydrocarbon group which may have a substituent, or a group represented by general formula (1-an1), (1-an2) or (1-an3), provided that at least one of R2 and R4 represents a group represented by general formula (1-an1), (1-an2) or (1-an3); and n0 is preferably 0 or 1, and wherein Y1 represents a single bond or —SO2—; R5 represents a linear or branched monovalent hydrocarbon group of 1 to 10 carbon atoms, cyclic monovalent hydrocarbon group of 3 to 20 carbon atoms or monovalent hydrocarbon group of 3 to 20 carbon atoms having a cyclic partial structure which may be substituted with a fluorine atom; and M+ represents an organic caType: GrantFiled: April 18, 2012Date of Patent: April 14, 2015Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Yoshitaka Komuro, Yoshiyuki Utsumi, Akiya Kawaue, Masatoshi Arai
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Patent number: 9005870Abstract: According to one embodiment, an actinic-ray- or radiation-sensitive resin composition includes a resin (P) containing a repeating unit (A) that when exposed to actinic rays or radiation, is decomposed to thereby generate an acid and at least two types of repeating units B1), (B2) that when acted on by an acid, are decomposed to thereby generate an alkali-soluble group, wherein the alkali-soluble group generated by the repeating unit (B1) is different from the alkali-soluble group generated by the repeating unit (B2).Type: GrantFiled: January 27, 2011Date of Patent: April 14, 2015Assignee: FUJIFILM CorporationInventors: Hidenori Takahashi, Shuji Hirano, Hideaki Tsubaki
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Publication number: 20150099228Abstract: A resist composition comprises a metal compound obtained from reaction of a starting metal compound having formula (A-1) or a (partial) hydrolyzate or condensate or (partial) hydrolytic condensate thereof, with a di- or trihydric alcohol having formula (A-2). M(OR1A)4??(A-1) R2A(OH)m??(A-2) In formula (A-1), M is Ti, Zr or Hf, and R1A is alkyl. In formula (A-2), m is 2 or 3, R2A is a divalent group when m=2 or a trivalent group when m=3. The resist composition exhibits improved resolution and edge roughness when processed by the EB or EUV lithography.Type: ApplicationFiled: September 23, 2014Publication date: April 9, 2015Applicant: Shin-Etsu Chemical Co., Ltd.Inventors: Jun Hatakeyama, Kazuhiro Katayama, Seiichiro Tachibana
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Patent number: 8999631Abstract: An undercoat agent usable in phase separation of a layer formed on a substrate, the layer containing a block copolymer having a plurality of polymers bonded, the undercoat agent including a resin component, and 20 mol % to 80 mol % of all the structural units of the resin component being a structural unit derived from an aromatic ring-containing monomer; and a method of forming a pattern of a layer containing a block copolymer, the method including: step (1) coating the undercoat agent on a substrate (1), thereby forming a layer (2) composed of the undercoat agent, step (2) forming a layer (3) containing a block copolymer having a plurality of polymers bonded on the surface of the layer (2) composed of the undercoat agent, and subjecting the layer (3) containing the block copolymer to phase separation, and step (3) selectively removing a phase (3a) of at least one polymer of the plurality of copolymers constituting the block copolymer from the layer (3) containing the block copolymer.Type: GrantFiled: September 12, 2011Date of Patent: April 7, 2015Assignees: Tokyo Ohka Kogyo Co., Ltd., RikenInventors: Takahiro Senzaki, Takahiro Dazai, Ken Miyagi, Shigenori Fujikawa, Harumi Hayakawa, Mari Koizumi
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Patent number: 8999622Abstract: A pattern forming method, includes: (i) forming a film from a chemical amplification resist composition that contains (A) a resin capable of increasing a polarity of the resin (A) to decrease a solubility of the resin (A) for a developer containing an organic solvent by an action of an acid, (B) a compound capable of generating an acid upon irradiation with an actinic ray or radiation, and (C) a solvent; (ii) exposing the film; and (iii) performing development by using a developer containing an organic solvent, wherein the resin (A) has a structure in which a polar group is protected with a leaving group capable of decomposing and leaving by an action of an acid, and the leaving group contains a fluorine atom.Type: GrantFiled: December 28, 2012Date of Patent: April 7, 2015Assignee: FUJIFILM CorporationInventors: Kaoru Iwato, Shohei Kataoka
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Patent number: 8999625Abstract: Embodiments include a silicon-containing antireflective material including a silicon-containing base polymer, a non-polymeric silsesquioxane material, and a photoacid generator. The silicon-containing base polymer may contain chromophore moieties, transparent moieties, and reactive sites on an SiOx background, where x ranges from approximately 1 to approximately 2. Exemplary non-polymeric silsesquioxane materials include polyhedral oligomeric silsesquioxanes having acid labile side groups linked to hydrophilic groups Exemplary acid labile side groups may include tertiary alkyl carbonates, tertiary alkyl esters, tertiary alkyl ethers, acetals and ketals, Exemplary hydrophilic groups may include phenols, alcohols, carboxylic acids, amides, and sulfonamides.Type: GrantFiled: February 14, 2013Date of Patent: April 7, 2015Assignee: International Business Machines CorporationInventors: Martin Glodde, Wu-Song Huang, Javier Perez, Ratnam Sooriyakumaran, Takeshi Kinsho, Tsutomu Ogihara, Seiichiro Tachibana, Takafumi Ueda
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Patent number: 8993209Abstract: The present invention relates to a positive type photosensitive resin composition and an organic light emitting device black bank comprising the same, and more particularly, an organic light emitting device black bank comprising the photosensitive resin composition according to the exemplary embodiment of the present invention may further have a function of a black matrix without an additional process, such that it is possible to simplify a manufacturing process of the organic light emitting device and largely improve visibility.Type: GrantFiled: July 12, 2011Date of Patent: March 31, 2015Assignee: LG Chem, Ltd.Inventors: Sang-Woo Kim, Se-Jin Shin, Kyung-Jun Kim
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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