Pattern Elevated In Radiation Unexposed Areas Patents (Class 430/326)
  • Patent number: 10264785
    Abstract: 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: Grant
    Filed: May 1, 2017
    Date of Patent: April 23, 2019
    Assignee: HUNTSMAN PETROCHEMICAL LLC
    Inventor: Dave C Ferguson
  • Patent number: 10083832
    Abstract: 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: Grant
    Filed: March 24, 2017
    Date of Patent: September 25, 2018
    Assignee: Taiwan Semiconductor Manufacturing Co., Ltd.
    Inventors: Chen-Yu Liu, Chin-Hsiang Lin, Ching-Yu Chang, Ming-Hui Weng
  • Patent number: 10007179
    Abstract: 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: Grant
    Filed: October 19, 2016
    Date of Patent: June 26, 2018
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: Irvinder Kaur, Cong Liu, Kevin Rowell, Gerhard Pohlers, Mingqi Li
  • Patent number: 9926462
    Abstract: 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: Grant
    Filed: November 22, 2016
    Date of Patent: March 27, 2018
    Assignee: JSR CORPORATION
    Inventors: Kiyoshi Tanaka, Kazunori Kusabiraki, Takahiro Hayama, Motoyuki Shima
  • Patent number: 9696629
    Abstract: 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: Grant
    Filed: December 16, 2015
    Date of Patent: July 4, 2017
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: Irvinder Kaur, Cong Liu, Kevin Rowell
  • Patent number: 9653293
    Abstract: 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: Grant
    Filed: February 11, 2015
    Date of Patent: May 16, 2017
    Assignee: TOKYO ELECTRON LIMITED
    Inventor: Hidetami Yaegashi
  • Patent number: 9645494
    Abstract: 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: Grant
    Filed: December 11, 2007
    Date of Patent: May 9, 2017
    Assignee: NISSAN CHEMICAL INDUSTRIES, LTD.
    Inventors: Masakazu Kato, Takahiro Hamada, Tomoyuki Enomoto
  • Patent number: 9540535
    Abstract: 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: Grant
    Filed: March 28, 2013
    Date of Patent: January 10, 2017
    Assignee: JSR CORPORATION
    Inventors: Kiyoshi Tanaka, Kazunori Kusabiraki, Takahiro Hayama, Motoyuki Shima
  • Patent number: 9529266
    Abstract: 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: Grant
    Filed: December 22, 2014
    Date of Patent: December 27, 2016
    Assignee: TOKYO OHKA KOGYO CO., LTD.
    Inventors: Tomohiro Oikawa, Kazuishi Tanno
  • Patent number: 9519217
    Abstract: 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: Grant
    Filed: June 5, 2015
    Date of Patent: December 13, 2016
    Assignee: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Katsuya Takemura, Yoshinori Hirano
  • Patent number: 9448482
    Abstract: 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: Grant
    Filed: May 22, 2015
    Date of Patent: September 20, 2016
    Assignee: FUJIFILM Corporation
    Inventors: Kaoru Iwato, Takanobu Takeda, Hiroo Takizawa
  • Patent number: 9401450
    Abstract: 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: Grant
    Filed: December 5, 2014
    Date of Patent: July 26, 2016
    Assignee: SunPower Corporation
    Inventors: Timothy Weidman, David D. Smith
  • Patent number: 9399076
    Abstract: 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: Grant
    Filed: May 17, 2005
    Date of Patent: July 26, 2016
    Assignee: MEDTRONIC MINIMED, INC.
    Inventors: Yihua Yu, Jesper S. Kristensen
  • Patent number: 9316908
    Abstract: 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: Grant
    Filed: August 29, 2014
    Date of Patent: April 19, 2016
    Assignee: FUJIFILM Corporation
    Inventor: Koutarou Takahashi
  • Patent number: 9280052
    Abstract: 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: Grant
    Filed: February 11, 2014
    Date of Patent: March 8, 2016
    Assignee: Tokyo Electron Limited
    Inventors: Fumiko Iwao, Satoru Shimura
  • Patent number: 9184057
    Abstract: 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: Grant
    Filed: February 29, 2012
    Date of Patent: November 10, 2015
    Assignee: BASF SE
    Inventors: Andreas Klipp, Guenter Oetter, Sabrina Montero Pancera, Andrei Honciuc, Christian Bittner
  • Patent number: 9170488
    Abstract: 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: Grant
    Filed: June 17, 2014
    Date of Patent: October 27, 2015
    Assignee: JSR CORPORATION
    Inventors: Hirokazu Sakakibara, Taiichi Furukawa, Reiko Kimura, Masafumi Hori
  • Patent number: 9164384
    Abstract: 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: Grant
    Filed: April 10, 2014
    Date of Patent: October 20, 2015
    Assignee: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Masaki Ohashi, Masahiro Fukushima, Tomohiro Kobayashi, Kazuhiro Katayama, Chuanwen Lin
  • Patent number: 9122147
    Abstract: 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: Grant
    Filed: January 16, 2014
    Date of Patent: September 1, 2015
    Assignee: SHIN-ESTU CHEMICAL CO., LTD.
    Inventors: Jun Hatakeyama, Tsutomu Ogihara
  • Patent number: 9116437
    Abstract: 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: Grant
    Filed: June 14, 2010
    Date of Patent: August 25, 2015
    Assignee: FUJIFILM Corporation
    Inventors: Yuichiro Enomoto, Sou Kamimura, Shinji Tarutani
  • Patent number: 9104107
    Abstract: 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: Grant
    Filed: May 29, 2013
    Date of Patent: August 11, 2015
    Assignee: Western Digital (Fremont), LLC
    Inventors: Xianzhong Zeng, Hai Sun
  • Patent number: 9080018
    Abstract: 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: Grant
    Filed: February 27, 2013
    Date of Patent: July 14, 2015
    Assignee: NIPPON SODA CO., LTD.
    Inventors: Kenichi Hayashi, Masamichi Yasuhara, Makoto Toyooka, Hideki Maekawa
  • Patent number: 9052603
    Abstract: 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: Grant
    Filed: January 31, 2014
    Date of Patent: June 9, 2015
    Assignee: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Jun Hatakeyama, Tsutomu Ogihara, Yusuke Biyajima
  • Publication number: 20150147697
    Abstract: 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: Application
    Filed: November 25, 2014
    Publication date: May 28, 2015
    Applicant: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Jun Hatakeyama, Masayoshi Sagehashi
  • Patent number: 9040220
    Abstract: 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: Grant
    Filed: March 2, 2012
    Date of Patent: May 26, 2015
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hideo Hada, Yoshiyuki Utsumi, Keita Ishiduka, Kensuke Matsuzawa, Fumitake Kaneko, Kyoko Ohshita, Hiroaki Shimizu, Yasuhiro Yoshii
  • Patent number: 9034556
    Abstract: 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: Grant
    Filed: December 18, 2008
    Date of Patent: May 19, 2015
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hideo Hada, Yoshiyuki Utsumi, Keita Ishiduka, Kensuke Matsuzawa, Fumitake Kaneko, Kyoko Ohshita, Hiroaki Shimizu, Yasuhiro Yoshii
  • Patent number: 9034558
    Abstract: 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: Grant
    Filed: September 28, 2011
    Date of Patent: May 19, 2015
    Assignee: FUJIFILM Corporation
    Inventors: Shuhei Yamaguchi, Akinori Shibuya, Yusuke Iizuka
  • Patent number: 9034557
    Abstract: 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: Grant
    Filed: June 1, 2010
    Date of Patent: May 19, 2015
    Assignee: FUJIFILM ELECTRONIC MATERIALS U.S.A., INC.
    Inventors: Ognian N. Dimov, Binod B. De
  • Patent number: 9029075
    Abstract: 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: Grant
    Filed: December 6, 2012
    Date of Patent: May 12, 2015
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventor: Jun Hatakeyama
  • Patent number: 9029062
    Abstract: 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: Grant
    Filed: June 30, 2010
    Date of Patent: May 12, 2015
    Assignee: Taiwan Semiconductor Manufacturing Company, Ltd.
    Inventors: Chien-Wei Wang, Chun-Ching Huang
  • Patent number: 9023581
    Abstract: 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: Grant
    Filed: June 14, 2011
    Date of Patent: May 5, 2015
    Assignee: Tokyo Ohka Kogyo Co., Ltd
    Inventors: Akiya Kawaue, Kazushige Dohtani, Yoshiyuki Utsumi, Jun Iwashita, Kenri Konno, Daiju Shiono, Daichi Takaki
  • Patent number: 9023585
    Abstract: 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: Grant
    Filed: June 20, 2013
    Date of Patent: May 5, 2015
    Assignee: Tokyo Ohka Kogyo Co., Ltd
    Inventors: Tsuyoshi Nakamura, Jiro Yokoya, Hideto Nito, Hiroaki Shimizu
  • Publication number: 20150118621
    Abstract: 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: Application
    Filed: January 2, 2015
    Publication date: April 30, 2015
    Applicant: FUJIFILM Corporation
    Inventors: Toshiaki FUKUHARA, Kaoru IWATO
  • Patent number: 9017918
    Abstract: 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: Grant
    Filed: June 1, 2011
    Date of Patent: April 28, 2015
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Seiichiro Tachibana, Koji Hasegawa
  • Patent number: 9017905
    Abstract: 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: Grant
    Filed: September 23, 2013
    Date of Patent: April 28, 2015
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Masashi Iio, Katsuya Takemura, Takashi Miyazaki, Hideyoshi Yanagisawa
  • Patent number: 9012129
    Abstract: 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: Grant
    Filed: January 6, 2014
    Date of Patent: April 21, 2015
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hideo Hada, Yoshiyuki Utsumi, Takehiro Seshimo, Akiya Kawaue
  • Patent number: 9012123
    Abstract: 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: Grant
    Filed: March 26, 2009
    Date of Patent: April 21, 2015
    Assignee: FUJIFILM Corporation
    Inventors: Kei Yamamoto, Akinori Shibuya
  • Patent number: 9012126
    Abstract: 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: Grant
    Filed: June 15, 2012
    Date of Patent: April 21, 2015
    Assignee: AZ Electronic Materials (Luxembourg) S.A.R.L.
    Inventors: Weihong Liu, PingHung Lu, Chunwei Chen, Stephen Meyer, Medhat Toukhy, SookMee Lai
  • Patent number: 9005872
    Abstract: 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: Grant
    Filed: February 16, 2012
    Date of Patent: April 14, 2015
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hiroaki Shimizu, Sho Abe, Hideto Nito
  • Patent number: 9005871
    Abstract: 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: Grant
    Filed: October 8, 2009
    Date of Patent: April 14, 2015
    Assignee: BASF SE
    Inventors: Hitoshi Yamato, Toshikage Asakura, Yuichi Nishimae
  • Patent number: 9005874
    Abstract: 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 ca
    Type: Grant
    Filed: April 18, 2012
    Date of Patent: April 14, 2015
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Yoshitaka Komuro, Yoshiyuki Utsumi, Akiya Kawaue, Masatoshi Arai
  • Patent number: 9005880
    Abstract: 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: Grant
    Filed: November 19, 2009
    Date of Patent: April 14, 2015
    Assignee: Rohm and Haas Electronic Materials, LLC
    Inventors: Deyan Wang, Chunyi Wu, George G. Barclay, Cheng-Bai Xu
  • Patent number: 9005870
    Abstract: 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: Grant
    Filed: January 27, 2011
    Date of Patent: April 14, 2015
    Assignee: FUJIFILM Corporation
    Inventors: Hidenori Takahashi, Shuji Hirano, Hideaki Tsubaki
  • Publication number: 20150099228
    Abstract: 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: Application
    Filed: September 23, 2014
    Publication date: April 9, 2015
    Applicant: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Kazuhiro Katayama, Seiichiro Tachibana
  • Patent number: 8999622
    Abstract: 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: Grant
    Filed: December 28, 2012
    Date of Patent: April 7, 2015
    Assignee: FUJIFILM Corporation
    Inventors: Kaoru Iwato, Shohei Kataoka
  • Patent number: 8999625
    Abstract: 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: Grant
    Filed: February 14, 2013
    Date of Patent: April 7, 2015
    Assignee: International Business Machines Corporation
    Inventors: Martin Glodde, Wu-Song Huang, Javier Perez, Ratnam Sooriyakumaran, Takeshi Kinsho, Tsutomu Ogihara, Seiichiro Tachibana, Takafumi Ueda
  • Patent number: 8999631
    Abstract: 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: Grant
    Filed: September 12, 2011
    Date of Patent: April 7, 2015
    Assignees: Tokyo Ohka Kogyo Co., Ltd., Riken
    Inventors: Takahiro Senzaki, Takahiro Dazai, Ken Miyagi, Shigenori Fujikawa, Harumi Hayakawa, Mari Koizumi
  • Patent number: 8993214
    Abstract: 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: Grant
    Filed: May 15, 2012
    Date of Patent: March 31, 2015
    Assignee: AZ Electronic Materials USA Corp.
    Inventors: Daishi Yokoyama, Takashi Fuke, Yuji Tashiro, Takashi Sekito, Toshiaki Nonaka
  • Patent number: 8993210
    Abstract: A salt represented by the formula (I): wherein R1 and R2 each independently represent a fluorine atom or a C1-C6 perfluoroalkyl group, X1 represents a C1-C17 divalent saturated hydrocarbon group which can have one or more fluorine atoms and in which one or more —CH2— can be replaced by —O— or —CO—, R3 represents a group having a cyclic ether structure, and Z1+ represents an organic cation.
    Type: Grant
    Filed: February 15, 2011
    Date of Patent: March 31, 2015
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Hiromu Sakamoto
  • Patent number: 8993212
    Abstract: 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: Grant
    Filed: October 14, 2011
    Date of Patent: March 31, 2015
    Assignee: Central Glass Company, Limited
    Inventors: Ryozo Takihana, Satoru Narizuka