Radiation Sensitive Composition Or Product Or Process Of Making Patents (Class 430/270.1)
  • Patent number: 10031419
    Abstract: There is provided a pattern forming method comprising (i) forming a film on a substrate using an actinic ray-sensitive or radiation-sensitive resin composition which contains (A) a resin which decomposes due to an action of an acid to change its solubility with respect to a developer and (C) a specific resin, (ii) forming a top coat layer using a top coat composition which contains a resin (T) on the film, (iii) exposing the film which has the top coat layer to actinic rays or radiation, and (iv) forming a pattern by developing the film which has the top coat layer after the exposing.
    Type: Grant
    Filed: October 23, 2015
    Date of Patent: July 24, 2018
    Assignee: FUJIFILM Corporation
    Inventors: Hiroo Takizawa, Shuji Hirano
  • Patent number: 10032633
    Abstract: An EUV lithographic structure includes an EUV photosensitive resist layer disposed on a hardmask layer, wherein the EUV lithographic structure is free of an antireflective coating. An organic adhesion layer can be provided between the hardmask layer and the EUV photosensitive resist layer. The hardmask layer can include an uppermost oxide hardmask layer, an intermediate hardmask layer, and a lowermost oxide hardmask layer, wherein the EUV photosensitive resist layer is disposed on the uppermost oxide hardmask layer. Also described are methods for patterning the EUV lithographic structures.
    Type: Grant
    Filed: January 17, 2017
    Date of Patent: July 24, 2018
    Assignee: INTERNATIONAL BUSINESS MACHINES CORPORATION
    Inventors: Hsueh-Chung Chen, Yann A. M. Mignot, Yongan Xu
  • Patent number: 10025180
    Abstract: A sulfonium salt containing an acid-eliminatable substituent group which is effective for improving contrast is highly soluble and uniformly dispersible. A resist composition comprising the sulfonium salt as photoacid generator forms a pattern with a high resolution, rectangularity, and reduced LWR.
    Type: Grant
    Filed: August 30, 2017
    Date of Patent: July 17, 2018
    Assignee: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Ryo Mitsui, Takayuki Fujiwara, Ryosuke Taniguchi, Koji Hasegawa, Masaki Ohashi
  • Patent number: 10023674
    Abstract: A monomer having a substituent group capable of polarity switch under the action of acid is provided. A useful polymer is obtained by polymerizing the monomer. A resist composition comprising the polymer has improved development properties and is processed to form a negative pattern having high resolution and etch resistance which is insoluble in alkaline developer.
    Type: Grant
    Filed: February 7, 2017
    Date of Patent: July 17, 2018
    Assignee: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Masayoshi Sagehashi, Masahiro Fukushima, Koji Hasegawa, Teppei Adachi, Kazuhiro Katayama, Jun Hatakeyama
  • Patent number: 10025186
    Abstract: The present invention has an object to provide an active-light-sensitive or radiation-sensitive resin composition having high DOF and low LWR; a pattern forming method using the composition; and a method for manufacturing an electronic device. The active-light-sensitive or radiation-sensitive resin composition of the present invention includes a resin P and a compound that generates an acid upon irradiation with active light or radiation, in which the resin P has a repeating unit p1 and a repeating unit p2 represented by specific formulae, and the repeating unit p2 does not have a group in which a hydroxy group of a hydroxyadamantyl group is protected with a group that decomposes by the action of an acid to leave.
    Type: Grant
    Filed: February 28, 2017
    Date of Patent: July 17, 2018
    Assignee: FUJIFILM Corporation
    Inventors: Akiyoshi Goto, Masafumi Kojima, Keita Kato, Keiyu Ou, Michihiro Shirakawa
  • Patent number: 10018911
    Abstract: A chemically amplified resist material comprises a polymer component that is capable of being made soluble or insoluble in a developer solution by an action of an acid, and a generative component that is capable of generating a radiation-sensitive sensitizer and an acid upon an exposure. The radiation-sensitive acid-and-sensitizer generating agent or the radiation-sensitive acid generating agent included in the generative component comprises the first compound that is radiation-sensitive and second compound that is radiation-sensitive. The first compound includes a first onium cation and a first anion, and the second compound includes a second onium cation and a second anion that is different from the first anion. Each of an energy released upon reduction of the first onium cation to a radical and an energy released upon reduction of the second onium cation to a radical is less than 5.0 eV.
    Type: Grant
    Filed: November 9, 2016
    Date of Patent: July 10, 2018
    Assignee: JSR CORPORATION
    Inventors: Hisashi Nakagawa, Takehiko Naruoka, Tomoki Nagai
  • Patent number: 10012902
    Abstract: A non-chemically-amplified positive resist composition comprising a polymer comprising both recurring units derived from a sulfonium salt capable of generating a fluorinated acid and recurring units containing an amino group as a base resin exhibits a high resolution and a low edge roughness and forms a pattern of good profile after exposure and organic solvent development.
    Type: Grant
    Filed: February 16, 2017
    Date of Patent: July 3, 2018
    Assignee: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Jun Hatakeyama, Teppei Adachi, Masaki Ohashi
  • Patent number: 10011682
    Abstract: Methods for preparing water soluble, non-peptidic polymers carrying carboxyl functional groups, particularly carboxylic acid functionalized poly(ethylene glycol) (PEG) polymers are disclosed, as are the products of these methods. In general, an ester reagent R(C?O)OR?, wherein R? is a tertiary group and R comprises a functional group X, is reacted with a water soluble, non-peptidic polymer POLY-Y, where Y is a functional group which reacts with X to form a covalent bond, to form a tertiary ester of the polymer, which is then treated with a strong base in aqueous solution, to form a carboxylate salt of the polymer. Typically, this carboxylate salt is then treated with an inorganic acid in aqueous solution, to convert the carboxylate salt to a carboxylic acid, thereby forming a carboxylic acid functionalized polymer.
    Type: Grant
    Filed: June 19, 2013
    Date of Patent: July 3, 2018
    Assignee: NEKTAR THERAPEUTICS
    Inventors: J. Milton Harris, Antoni Kozlowski, Lihong Guo
  • Patent number: 10007182
    Abstract: Provided are a photoresist composition and a method of manufacturing a semiconductor device using the same. The method of manufacturing a semiconductor device comprises forming a mask layer and a photoresist layer on a substrate, forming a photoresist pattern by patterning the photoresist layer, forming a mask pattern by patterning the mask layer through the photoresist pattern and forming a pattern by etching the substrate using the mask pattern, wherein the formation of the photoresist layer comprises forming the photoresist layer, using a photoresist composition comprising a polymer which includes a protecting group that causes decarboxylation by radical.
    Type: Grant
    Filed: October 14, 2016
    Date of Patent: June 26, 2018
    Assignee: SAMSUNG ELECTRONICS CO., LTD.
    Inventors: Jin Park, Hyun Woo Kim, Jin Kyu Han
  • Patent number: 10007178
    Abstract: A positive resist composition is provided comprising a polymer having an acid labile group and an acid generator bound to its backbone, in admixture with an onium salt having a specific cation structure capable of generating sulfonic acid having a molecular weight of at least 540. The composition is effective for suppressing acid diffusion, has high resolution, and forms a pattern of satisfactory profile and minimal edge roughness after exposure and development.
    Type: Grant
    Filed: July 20, 2015
    Date of Patent: June 26, 2018
    Assignee: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Jun Hatakeyama, Masaki Ohashi, Masahiro Fukushima
  • Patent number: 10005922
    Abstract: An active ray-curable composition characterized by containing a photobase generator, a double bond-containing compound, and a ?-dicarbonyl compound.
    Type: Grant
    Filed: July 31, 2013
    Date of Patent: June 26, 2018
    Assignees: RICOH COMPANY, LTD., Tokyo University of Science Foundation
    Inventors: Soh Noguchi, Okitoshi Kimura, Koji Arimitsu
  • Patent number: 10005714
    Abstract: Provided are a novel alicyclic ester compound and a method for producing a compound of general formula (1) at a high yield from a compound of general formula (2) and a compound of general formula (3). An adamantane compound expressed by general formula (2) and a hydroxyalkyl (meth)acrylate ester compound expressed by general formula (3) are reacted with each other by use of a dehydration condensation agent as a catalyst to obtain an alicyclic ester compound expressed by general formula (1).
    Type: Grant
    Filed: February 12, 2015
    Date of Patent: June 26, 2018
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Hiroyuki Tanagi, Hiroshi Horikoshi, Kikuo Furukawa, Shoichi Hayakawa, Hiroyasu Tanaka
  • Patent number: 10007181
    Abstract: A chemically amplified positive resist dry film to be formed on a support film contains 5-40 wt % of a component having a boiling point of 55-250° C. under atmospheric pressure. The resist dry film having flexibility and dimensional stability can be prepared through simple steps. The resist dry film can be efficiently and briefly laid on an article and processed to form a pattern.
    Type: Grant
    Filed: September 1, 2015
    Date of Patent: June 26, 2018
    Assignee: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Yoshinori Hirano, Satoshi Asai, Hideyoshi Yanagisawa
  • Patent number: 9996003
    Abstract: Provided are an active-light-sensitive or radiation-sensitive resin composition having high depth of focus and excellent resolving power; a pattern forming method using the composition; and a method for manufacturing an electronic device.
    Type: Grant
    Filed: January 6, 2017
    Date of Patent: June 12, 2018
    Assignee: FUJIFILM Corporation
    Inventors: Akiyoshi Goto, Masafumi Kojima, Michihiro Shirakawa, Keita Kato
  • Patent number: 9994513
    Abstract: Provided are a resist and a compound for the resist improving the sensitivity, the resolution and the line edge roughness (LER) in a good balance without spoiling basic properties of a chemical amplification resist such as pattern shape, dry etching resistance, heat resistance and the like. Provided are a method for producing an alicyclic ester compound expressed by general formula (1), an alicyclic ester compound expressed by general formula (1), a (meth)acrylic copolymer obtained by polymerization of the alicyclic ester compound, and a photosensitive resin composition containing the (meth)acrylic copolymer. A method for producing an alicyclic ester compound expressed by general formula (1) includes reacting an adamantane compound expressed by general formula (2) with hydroxyalkylamine expressed by general formula (3) to produce an adamantaneamide compound expressed by general formula (4), and then reacting the adamantaneamide compound expressed by general formula (4) with (meth)acrylic acid.
    Type: Grant
    Filed: February 12, 2015
    Date of Patent: June 12, 2018
    Assignee: Mitsubishi Gas Chemical, Inc.
    Inventors: Shoichi Hayakawa, Hiroshi Horikoshi, Kikuo Furukawa, Hiroyasu Tanaka, Hiroyuki Tanagi
  • Patent number: 9989854
    Abstract: An object of the present invention is to provide a photosensitive resin composition for projection exposure capable of forming a resist pattern that is excellent in adhesion, resolution, and inhibitory properties against the occurrence of resist footing, and the present invention provides a photosensitive resin composition for projection exposure comprising (A) a binder polymer; (B) a photopolymerizable compound having an ethylenically unsaturated bond; (C) a photopolymerization initiator; and (D) a sensitizing dye, wherein the (B) photopolymerizable compound having an ethylenically unsaturated bond comprises a (meth)acrylate compound having a skeleton derived from dipentaerythritol and a compound represented by the following formula (III): wherein R8, R9, R10, and R11 each independently represent a hydrogen atom or a methyl group, X and Y each independently represent an ethylene group or a propylene group, p1, p2, q1, and q2 each independently represent a numerical value of 0 to 9, both p1+q1 and p2+q2
    Type: Grant
    Filed: July 22, 2014
    Date of Patent: June 5, 2018
    Assignee: HITACHI CHEMICAL COMPANY, LTD.
    Inventors: Masakazu Kume, Momoko Munakata
  • Patent number: 9983475
    Abstract: Non-ionic photo-acid generating (PAG) compounds were prepared that contain an aryl ketone group having a perfluorinated substituent alpha to the ketone carbonyl. The non-polymeric PAGs release a sulfonic acid when exposed to high energy radiation such as deep UV or extreme UV light. The photo-generated sulfonic acid has a low diffusion rate in an exposed resist layer subjected to a post-exposure bake (PEB) at 100° C. to 150° C., resulting in formation of good line patterns after development. At higher temperatures, the PAGs can also undergo a thermal reaction to form a sulfonic acid. The perfluorinated substituent provides improved thermal stability and hydrolytic/nucleophilic stability.
    Type: Grant
    Filed: August 12, 2016
    Date of Patent: May 29, 2018
    Assignees: International Business Machines Corporation, Central Glass Co., Ltd.
    Inventors: Takehisa Ishimaru, Satoru Narizuka, Daniel P. Sanders, Ratnam Sooriyakumaran, Hoa D. Truong, Rudy J. Wojtecki
  • Patent number: 9983474
    Abstract: The present disclosure is directed to a photoresist and a method of performing a lithography process using the photoresist. The photoresist contains a polymer and a photo-acid generator. The photo-acid generator contains a sensitizer component, an acid generator component, and a bonding component that bonds the sensitizer component to the acid generator component. The bonding component may be either a single bond or a conjugated bond. The lithography process may be an EUV lithography process or an e-beam lithography process.
    Type: Grant
    Filed: September 11, 2015
    Date of Patent: May 29, 2018
    Assignee: TAIWAN SEMICONDUCTOR MANUFACTURING COMPANY, LTD.
    Inventors: Yen-Hao Chen, Chien-Wei Wang
  • Patent number: 9975830
    Abstract: The present invention provides a compound containing a modified phenolic hydroxy group, which has a molecular structure represented by General Formula (1) except for a molecular structure represented by the following General Formula (2). In the formulas, R1 represents a tertiary alkyl group, an alkoxyalkyl group, an aryloxyalkyl group, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a cyclic aliphatic hydrocarbon group containing a hetero atom, or a trialkylsilyl group; R2 represents a hydrogen atom, an alkyl group, an alkoxy group, an aryl group which may have a substituent, an aralkyl group which may have a substituent, or a halogen atom; and R3 represents an alkyl group which may have a substituent or an aryl group which may have a substituent.
    Type: Grant
    Filed: April 16, 2015
    Date of Patent: May 22, 2018
    Assignee: DIC Corporation
    Inventor: Tomoyuki Imada
  • Patent number: 9977331
    Abstract: A resist overlayer film forming composition for use in a lithography process in semiconductor device production does not intermix with a resist, blocks undesirable exposure light particularly in EUV exposure, for example, UV and DUV and selectively transmits EUV alone, and can be developed with a developer after exposure.
    Type: Grant
    Filed: February 13, 2015
    Date of Patent: May 22, 2018
    Assignee: NISSAN CHEMICAL INDUSTRIES, LTD.
    Inventors: Noriaki Fujitani, Rikimaru Sakamoto
  • Patent number: 9975996
    Abstract: A method for manufacturing a polyhydroxyamide resin (A) containing no chloride includes reacting a coumarin dimer component of Formula (19), where R56, R57, R58, R59, R60 and R61 independently represent an alkyl group having 1 to 10 carbon atom(s), a halogen atom, a nitro group, an amino group, a cyano group, a carboxy group, an alkoxycarbonyl group having 1 to 10 carbon atom(s), a halogenated alkyl group having 1 to 10 carbon atom(s) or a hydroxy group, and a dimamine in a polar solvent.
    Type: Grant
    Filed: March 8, 2016
    Date of Patent: May 22, 2018
    Assignee: NISSAN CHEMICAL INDUSTRIES, LTD.
    Inventors: Kazuya Ebara, Hideo Suzuki, Takayuki Tamura
  • Patent number: 9969829
    Abstract: The present invention provides a polymer compound containing a repeating unit shown by the following general formula (1). There can be provided a polymer compound usable in a negative resist composition that can achieve high resolution of 50 nm or less and small LER and cause very few defects, a negative resist composition using the polymer compound, and a patterning process using the negative resist composition.
    Type: Grant
    Filed: January 5, 2017
    Date of Patent: May 15, 2018
    Assignee: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Daisuke Domon, Koji Hasegawa, Keiichi Masunaga, Masaaki Kotake
  • Patent number: 9963578
    Abstract: Black polyimides polymer and a method of synthesizing the same have been developed. The black polyimide polymer includes at least one acid monomer, at least one diamino monomer and a solvent-soluble black dye. The acid and diamino monomers having been reacting in a solvent under suitable conditions to form a polyimide precursor polymer.
    Type: Grant
    Filed: July 17, 2013
    Date of Patent: May 8, 2018
    Assignee: NeXolve Corporation
    Inventors: Brandon S. Farmer, Garrett D. Poe, David L. Rodman, Lonnie F. Bradburn, Jr.
  • Patent number: 9964849
    Abstract: The method for forming a resin cured film pattern according to the invention comprises a first step in which there is formed on a base material a photosensitive layer composed of a photosensitive resin composition comprising a binder polymer with a carboxyl group having an acid value of 75 mgKOH/g or greater, a photopolymerizable compound and a photopolymerization initiator, and having a thickness of 10 ?m or smaller, a second step in which prescribed sections of the photosensitive layer are cured by irradiation with active light rays, and a third step in which the sections of the photosensitive layer other than the prescribed sections are removed to form a cured film pattern of the prescribed sections of the photosensitive layer, wherein the photosensitive resin composition comprises an oxime ester compound and/or a phosphine oxide compound as the photopolymerization initiator.
    Type: Grant
    Filed: March 15, 2017
    Date of Patent: May 8, 2018
    Assignee: HITACHI CHEMICAL COMPANY, LTD.
    Inventors: Yasuharu Murakami, Hiroshi Yamazaki, Yoshimi Igarashi, Naoki Sasahara, Ikuo Mukai
  • Patent number: 9963573
    Abstract: This invention relates to a polymeric pipe, and more particularly a polymeric pipe where the pipe comprises a crosslinked polyolefin formed from extruded polyolefin comprising a photoinitiator and a reactive extrusion species. More particularly, this invention relates to the manufacturing of plastic pipes and tubing by utilizing co-rotating twin screw extrusion combined with photo-induced crosslinking, of thermoplastic polymers such as polyethylene, to produce PEX pipes and tubing.
    Type: Grant
    Filed: April 23, 2014
    Date of Patent: May 8, 2018
    Assignee: Uponor Innovation AB
    Inventors: Jan Ericsson, Andrew Ortquist, Todd Menssen, Jacob John, Josh Meeker
  • Patent number: 9965124
    Abstract: A method for patterning a light transmitting electrically conductive member uses a light transmitting laminate material in which an electrically conductive layer including an overcoat layer and silver nanowires embedded therein is formed on a surface of a light transmitting base film and includes a step of treating a surface of the electrically conductive layer which is not covered with a resist layer using an iodine solution to at least partially iodize the silver nanowires and a step of applying a thiosulfate solution to the surface of the electrically conductive layer which is not covered with the resist layer to remove a silver iodide exposed to a surface of the overcoat layer. Since a white cloudy or a whitened silver iodide is removed, the optical transmission characteristics of the non-electrically conductive region can be improved.
    Type: Grant
    Filed: January 25, 2016
    Date of Patent: May 8, 2018
    Assignee: ALPS ELECTRIC CO., LTD.
    Inventors: Tomoyuki Yamai, Mitsuo Bito, Yasuyuki Kitamura
  • Patent number: 9958777
    Abstract: A resist composition comprising a base polymer and a sulfonium salt capable of generating fluorinated aminobenzoic acid offers a satisfactory dissolution contrast and minimal LWR independent of whether it is of positive or negative tone.
    Type: Grant
    Filed: January 18, 2017
    Date of Patent: May 1, 2018
    Assignee: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Jun Hatakeyama, Masaki Ohashi
  • Patent number: 9958781
    Abstract: A method comprises applying a composition on a substrate to form a coating film on the substrate. The coating film is heated in an atmosphere in which an oxygen concentration is less than 1% by volume and a temperature is higher than 450° C. and 800° C. or lower, to form a film on the substrate. The composition comprises a compound comprising an aromatic ring. The oxygen concentration in the atmosphere during the heating of the coating film is preferably no greater than 0.1% by volume. The temperature in the atmosphere during the heating of the coating film is preferably 500° C. or higher and 600° C. or lower.
    Type: Grant
    Filed: April 21, 2016
    Date of Patent: May 1, 2018
    Assignee: JSR CORPORATION
    Inventors: Yuushi Matsumura, Goji Wakamatsu, Naoya Nosaka, Tsubasa Abe, Yoshio Takimoto
  • Patent number: 9958780
    Abstract: In one aspect, the present invention relates to coating compositions that comprise a resin component, wherein the predominant portion of the resin component comprising one or more resins that are at least substantially free of fluorine. Coating compositions of the invention are useful as photoresist overcoat layers, including in immersion lithography processing.
    Type: Grant
    Filed: August 17, 2010
    Date of Patent: May 1, 2018
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: Deyan Wang, Peter Trefonas, III, Michael K. Gallagher
  • Patent number: 9958778
    Abstract: A photosensitive composition is disclosed including a fluorinated photo cross-linkable polymer provided in a fluorinated solvent such as a hydrofluoroether. The photo cross-linkable polymer includes a first repeating unit having a fluorine-containing group but not a cinnamate group, and a second repeating unit having a fluorine-containing cinnamate group. The polymer has a total fluorine content in a range of 30 to 60% by weight. The composition can be used to form patterned barrier or dielectric structures over substrates and devices such as organic electronic devices.
    Type: Grant
    Filed: February 4, 2015
    Date of Patent: May 1, 2018
    Assignee: ORTHOGONAL, INC.
    Inventors: Charles Warren Wright, Douglas Robert Robello, John Andrew DeFranco, Diane Carol Freeman, Frank Xavier Byrne
  • Patent number: 9958779
    Abstract: A patternable layer is formed over a substrate. A photo-sensitive layer is formed over the patternable layer. The photo-sensitive layer contains an additive. The additive contains at least a floating control chemical and a volume control chemical. A spin drying or a baking process is performed to the photo-sensitive layer. The floating control chemical causes the additive to rise upward during the spin drying or baking process. Thereafter, as a part of an extreme ultraviolet (EUV) lithography process, the photo-sensitive layer is exposed. One or more outgassing chemicals are generated inside the photo-sensitive layer during the exposing. The volume control chemical is sufficiently voluminous and dense to trap the outgassing chemicals inside the photo-sensitive layer.
    Type: Grant
    Filed: October 7, 2015
    Date of Patent: May 1, 2018
    Assignee: TAIWAN SEMICONDUCTOR MANUFACTURING COMPANY, LTD.
    Inventors: Wei-Han Lai, Ching-Yu Chang, Chien-Wei Wang
  • Patent number: 9958576
    Abstract: Provided are a near infrared ray absorbent composition which can form a cured film having excellent heat resistance while maintaining high near infrared ray shielding properties, and a near infrared ray cut filter, a manufacturing method of a near infrared ray cut filter, a solid image pickup element, and a camera module using the near infrared ray absorbent composition. The near infrared ray absorbent composition contains a compound having a partial structure represented by M-X, and a near infrared ray absorbent compound, and a content of the compound having a partial structure represented by M-X is greater than or equal to 15 mass % with respect to a total solid content of the near infrared ray absorbent composition.
    Type: Grant
    Filed: December 23, 2016
    Date of Patent: May 1, 2018
    Assignee: FUJIFILM Corporation
    Inventors: Takashi Kawashima, Keisuke Arimura
  • Patent number: 9952509
    Abstract: The present invention relates to a pattern forming method including: forming a film using an actinic ray-sensitive or radiation-sensitive resin composition that includes a (A) resin which has an increase in the polarity by the action of an acid, and thus, has a decrease in the solubility in a developer containing an organic solvent, a (B) compound capable of generating an acid upon irradiation with specific actinic ray or radiation, and a (C) solvent, exposing the film, and developing the exposed film using a developer including an organic solvent, in which the resin (A) has a structure in which a polar group is protected with a leaving group which decomposes to leave by the action of an acid, and the leaving group is a group represented by the following General Formula (I).
    Type: Grant
    Filed: July 1, 2016
    Date of Patent: April 24, 2018
    Assignee: FUJIFILM Corporation
    Inventors: Keita Kato, Keiyu Ou, Michihiro Shirakawa, Akiyoshi Goto, Masafumi Kojima
  • Patent number: 9951198
    Abstract: Matrix-filled liquid radiation curable resin compositions for additive fabrication are described and claimed. Such resins include a cationically polymerizable component that is an aliphatic epoxide, a multifunctional (meth)acrylate component, a cationic photoinitiator, a free-radical photo initiator, and a matrix of inorganic fillers, wherein the matrix further constitutes prescribed ratios of at least one microparticle constituent and at least one nanoparticle constituent. Also described and claimed is a process for using the matrix-filled liquid radiation curable resins for additive fabrication to create three dimensional parts, and the three-dimensional parts made from the liquid radiation curable resins for additive fabrication.
    Type: Grant
    Filed: November 25, 2015
    Date of Patent: April 24, 2018
    Assignee: DSM IP ASSETS, B.V.
    Inventors: Mingbo He, Beth Rundlett, Kangtai Ren, Caroline Liu, Tai Yeon Lee, Brad Seurer, Robin Papachristopoulos
  • Patent number: 9951182
    Abstract: Provided are [1] a xylylenediamine composition containing xylylenediamine and a 5-membered or 6-membered heterocyclic compound (A) having at least one nitrogen-containing substituent and having two nitrogen atoms as atoms constituting a ring, wherein the content of the heterocyclic compound (A) is 0.001 to 0.02 parts by mass based on 100 parts by mass of the xylylenediamine; and [2] a method for producing a polyamide resin including the steps of introducing a 5-membered or 6-membered heterocyclic compound (A) having at least one nitrogen-containing substituent and having two nitrogen atoms as atoms constituting a ring, a diamine including xylylenediamine (but excluding a diamine corresponding to the above-mentioned heterocyclic compound (A)), and a dicarboxylic acid into a reaction system and performing a polycondensation reaction, wherein the amount of the heterocyclic compound (A) to be introduced is 0.001 to 0.02 parts by mass based on 100 parts by mass of xylylenediamine.
    Type: Grant
    Filed: October 29, 2014
    Date of Patent: April 24, 2018
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Takashi Nakamura, Hajime Yamada, Tatsuya Tochihara, Katsumi Shinohara, Jun Mitadera, Takashi Yamamoto
  • Patent number: 9951159
    Abstract: A compound represented by formula (I), a resin including a structural unit derived from the compound and a resist composition including the resin: wherein R1 represents a hydrogen atom, a halogen atom or a C1 to C6 alkyl group in which a hydrogen atom may be replaced by a halogen atom, R2 represents a C1 to C6 perfluoroalkyl group or *—CHRf1Rf2, * represents a binding site to a carbonyl group, Rf1 and Rf2 each independently represent a C1 to C4 perfluoroalkyl group or Rf1 and Rf2 may be bonded together with a carbon atom bonded thereto to form a ring, A1 represents a single bond, a C1 to C6 alkanediyl group or **-A3-X1-(A4-X2)a-(A5)b-, ** represents a binding site to an oxygen atom, A2, A3, A4 and A5 each independently represent a C1 to C6 alkanediyl group, X1 and X2 each independently represent —O—, —CO—O— or —O—CO—, a and b each represent 0 or 1, and W1 represents a C5 to C18 divalent alicyclic hydrocarbon group.
    Type: Grant
    Filed: November 10, 2015
    Date of Patent: April 24, 2018
    Assignee: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Yukako Anryu, Singo Fujita, Koji Ichikawa
  • Patent number: 9951164
    Abstract: Non-ionic photo-acid generating (PAG) polymerizable monomers were prepared that contain a side chain sulfonate ester of an alpha-hydroxy aryl ketone. The aryl ketone group has a perfluorinated substituent alpha to the ketone carbonyl. The sulfur of the sulfonate ester is also directly linked to a fluorinated group. PAG polymers prepared from the PAG monomers release a strong sulfonic acid when exposed to high energy radiation such as deep UV or extreme UV light. The photo-generated sulfonic acid has a low diffusion rate in an exposed resist layer subjected to a post-exposure bake (PEB) at 100° C. to 150° C., resulting in formation of good line patterns after development.
    Type: Grant
    Filed: August 12, 2016
    Date of Patent: April 24, 2018
    Assignees: International Business Machines Corporation, Central Glass Co., Ltd.
    Inventors: Takehisa Ishimaru, Satoru Narizuka, Daniel P. Sanders, Ratnam Sooriyakumaran, Hoa D. Truong, Rudy J. Wojtecki
  • Patent number: 9950999
    Abstract: Non-ionic photo-acid generating (PAG) compounds were prepared that contain an aryl ketone group. The disclosed non-polymeric PAGs release a strong sulfonic acid when exposed to high energy radiation such as deep UV or extreme UV light. The photo-generated sulfonic acid has a low diffusion rate in an exposed resist layer subjected to a post-exposure bake (PEB) at 100° C. to 150° C., resulting in formation of good line patterns after development. At higher temperatures, the PAGs undergo a thermal reaction to form a sulfonic acid.
    Type: Grant
    Filed: August 12, 2016
    Date of Patent: April 24, 2018
    Assignees: International Business Machines Corporation, Central Glass Co., Ltd.
    Inventors: Takehisa Ishimaru, Satoru Narizuka, Daniel P. Sanders, Ratnam Sooriyakumaran, Hoa D. Truong, Rudy J. Wojtecki
  • Patent number: 9944730
    Abstract: Embodiments encompassing a series of compositions containing polymers of norbornadiene and maleic anhydride monomers which are useful in forming a variety of photopatternable structures are disclosed and claimed. The compositions are useful as permanent dielectric materials. More specifically, embodiments encompassing compositions containing a series of ter- and tetrapolymers of a variety of norbornadiene, maleic anhydride, maleimide and norbornene-type cycloolefinic monomers in which maleic anhydride is fully or partially hydrolyzed (i.e., ring opened and fully or partially esterified), and a photoactive compound are disclosed, which are useful in forming permanent dielectric materials having utility in a variety of electronic material applications, among various other uses.
    Type: Grant
    Filed: October 12, 2017
    Date of Patent: April 17, 2018
    Assignee: PROMERUS, LLC
    Inventors: Larry F Rhodes, Pramod Kandanarachchi
  • Patent number: 9946157
    Abstract: A resist composition contains: a novolak resin (A1) having a protective group capable of being cleaved by action of an acid, an acid generator (B), an anticorrosive agent (G), and a solvent (D) as well as a method for producing a resist pattern includes steps (1) to (4); (1) applying the resist composition according to the above onto a substrate; (2) drying the applied composition to form a composition layer; (3) exposing the composition layer; and (4) developing the exposed composition layer.
    Type: Grant
    Filed: March 30, 2016
    Date of Patent: April 17, 2018
    Assignee: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Maki Kawamura, Makoto Akita
  • Patent number: 9932472
    Abstract: Disclosed is a method of preparing a rubber-reinforced thermoplastic resin. According to the present invention, a graft copolymer comprising a large-particle-size rubber polymer obtained by welding polymerization-heat-control-type small particles and a reactive emulsifier or a mixed emulsifier comprising a reactive emulsifier and a non-reactive emulsifier is prepared, and a rubber-reinforced thermoplastic resin comprising the same may have enhanced mechanical properties, thermal stability, surface visibility and gloss.
    Type: Grant
    Filed: July 22, 2014
    Date of Patent: April 3, 2018
    Assignee: LG CHEM, LTD.
    Inventors: Bong Keun Ahn, Keun Hoon Yoo, Dae Young Kim
  • Patent number: 9927707
    Abstract: A method for lithography patterning includes forming a material layer over a substrate; exposing a portion of the material layer to a radiation; and removing the exposed portion of the material layer in a developer, resulting in a patterned material layer. The developer comprises water, an organic solvent, and a basic solute. In an embodiment, the basic solute is less than 30% of the developer by weight.
    Type: Grant
    Filed: March 27, 2017
    Date of Patent: March 27, 2018
    Assignee: TAIWAN SEMICONDUCTOR MANUFACTURING CO., LTD.
    Inventors: Chen-Yu Liu, Ching-Yu Chang, Chin-Hsiang Lin
  • Patent number: 9921475
    Abstract: A photoacid-generating compound has the structure where R1, R2, R3, R4, Q, and X are defined herein. The photoacid-generating compound can be used as a component of a photoresist composition, or as a monomer incorporated into a polymer useful in a photoresist composition. The photoacid-generating compound provides a desired balance of solubility and line width roughness.
    Type: Grant
    Filed: August 31, 2016
    Date of Patent: March 20, 2018
    Assignee: ROHM AND HAAS ELECTRONIC MATERIALS LLC
    Inventors: Emad Aqad, William Williams, III, Cong Liu
  • Patent number: 9915870
    Abstract: There is provided a pattern forming method comprising (a) a step of forming a film on a substrate using an electron beam-sensitive or extreme ultraviolet radiation-sensitive resin composition, (b) a step of forming a top coat layer on the film using a top coat composition containing a resin (T) containing at least any one of repeating units represented by formulae (I-1) to (I-5) shown below, (c) a step of exposing the film having the top coat layer using an electron beam or an extreme ultraviolet radiation, and (d) a step of developing the film having the top coat layer after the exposure to form a pattern.
    Type: Grant
    Filed: September 14, 2015
    Date of Patent: March 13, 2018
    Assignee: FUJIFILM Corporation
    Inventors: Hiroo Takizawa, Kaoru Iwato
  • Patent number: 9910354
    Abstract: A composition for forming a resist underlayer film which make possible to form a desired high-adhesion resist pattern. A resist underlayer film-forming composition for lithography containing a polymer having the following structure Formula (1) or (2) at a terminal of a polymer chain, crosslinker, compound promoting crosslinking reaction, and organic solvent. (wherein R1 is a C1-6 alkyl group optionally having a substituent, phenyl group, pyridyl group, halogeno group, or hydroxy group, R2 is a hydrogen atom, a C1-6 alkyl group, hydroxy group, halogeno group, or ester group of —C(?O)O—X wherein X is a C1-6 alkyl group optionally having a substituent, R3 is a hydrogen atom, a C1-6 alkyl group, hydroxy group, or halogeno group, R4 is a direct bond or divalent C1-8 organic group, R5 is a divalent C1-8 organic group, A is an aromatic ring or heteroaromatic ring, t is 0 or 1, and u is 1 or 2.
    Type: Grant
    Filed: April 14, 2015
    Date of Patent: March 6, 2018
    Assignee: NISSAN CHEMICAL INDUSTRIES, LTD.
    Inventors: Yasushi Sakaida, Tokio Nishita, Noriaki Fujitani, Rikimaru Sakamoto
  • Patent number: 9904097
    Abstract: The present invention provides a method for manufacturing a quantum dot color filter substrate, in which a black photoresist layer and a transparent photoresist layer are first coated and formed on a backing plate in sequence and then, first, second, and third patterns of a photo mask having different grey levels are used to pattern the black photoresist layer and the transparent photoresist layer to obtain a plurality of transparent barrier walls corresponding to the first pattern, sub spacers corresponding to the second pattern and located on the transparent barrier walls, and main spacers corresponding to the third pattern and located on the transparent barrier walls and also to obtain a plurality of black barrier walls covered by the plurality of transparent barrier walls, the plurality of black barrier walls and the plurality of transparent barrier walls located thereon collectively defining a plurality of pixel barrier walls; and then, patterned quantum dot layers are formed in sub-pixel zones that are
    Type: Grant
    Filed: December 23, 2015
    Date of Patent: February 27, 2018
    Assignee: SHENZHEN CHINA STAR OPTOELECTRONICS TECHNOLOGY CO., LTD.
    Inventors: Lanyan Li, Yuheng Liang
  • Patent number: 9904168
    Abstract: An actinic ray-sensitive or radiation-sensitive resin composition includes a resin (A) containing a repeating unit represented by General Formula (4) and a crosslinking agent (C) containing a polar group, in which the crosslinking agent (C) is a compound represented by General Formula (1) or a compound in which two to five structures represented by General Formula (1) are connected via a linking group or a single bond represented by L1 in General Formula (3).
    Type: Grant
    Filed: July 8, 2016
    Date of Patent: February 27, 2018
    Assignee: FUJIFILM Corporation
    Inventors: Natsumi Yokokawa, Shuhei Yamaguchi, Koutarou Takahashi
  • Patent number: 9904172
    Abstract: A shrink material is provided comprising a specific polymer and a solvent containing an anti-vanishing solvent. A pattern is formed by applying a resist composition comprising a base resin and an acid generator onto a substrate to form a resist film, exposing, developing in an organic solvent developer to form a negative resist pattern, applying the shrink material onto the pattern, and removing the excessive shrink material with an organic solvent for thereby shrinking the size of holes and/or slits in the pattern.
    Type: Grant
    Filed: December 7, 2015
    Date of Patent: February 27, 2018
    Assignee: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Kentaro Kumaki, Satoshi Watanabe, Koji Hasegawa, Daisuke Domon, Kenji Yamada
  • Patent number: 9904169
    Abstract: A photomask blank has a chemically amplified negative resist film comprising (A) a polymer comprising recurring units of specific structure and recurring units having fluorine, (B) a base resin adapted to reduce its solubility in alkaline developer under the action of acid, (C) an acid generator, and (D) a basic compound. The resist film is improved in receptivity to antistatic film.
    Type: Grant
    Filed: April 4, 2016
    Date of Patent: February 27, 2018
    Assignee: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Teppei Adachi, Satoshi Watanabe, Daisuke Domon, Keiichi Masunaga
  • Patent number: 9897917
    Abstract: The present invention provides a conductive polymer composition including: (A) a ?-conjugated conductive polymer having at least one repeating unit shown by the following general formulae (1-1), (1-2), and (1-3); and (B) a dopant polymer which contains a repeating unit “a” shown by the following general formula (2) and has a weight-average molecular weight in a range of 1,000 to 500,000. The inventive conductive polymer composition has excellent antistatic performance in electron beam-resist drawing as well as good applicability onto a resist and peelability with H2O and an alkaline solution, thereby being suitably used for electron beam lithography.
    Type: Grant
    Filed: June 14, 2016
    Date of Patent: February 20, 2018
    Assignee: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Takayuki Nagasawa, Jun Hatakeyama