Radiation Sensitive Composition Or Product Or Process Of Making Patents (Class 430/270.1)
  • Patent number: 9563125
    Abstract: A non-ionic compound includes a group represented by formula (Ia): wherein R2 represents a group having a C5 to C18 alicyclic hydrocarbon group where a methylene group may be replaced by an oxygen atom or a carbonyl group, Rf1 and Rf2 each independently represent a C1 to C4 perfluoroalkyl group, and * represents a binding site.
    Type: Grant
    Filed: November 24, 2015
    Date of Patent: February 7, 2017
    Assignee: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Tatsuro Masuyama, Yuichi Mukai, Koji Ichikawa
  • Patent number: 9563123
    Abstract: A photoresist composition comprising: a resin having an acid-labile group, an acid generator, and a compound represented by formula (I): wherein R1, R2 and R3 each independently represents a C1-C24 hydrocarbon group in which a hydrogen atom can be replaced by a substituent and in which a methylene group can be replaced by an oxygen atom, a sulfur atom or a carbonyl group.
    Type: Grant
    Filed: March 2, 2015
    Date of Patent: February 7, 2017
    Assignee: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Tatsuro Masuyama, Shingo Fujita, Koji Ichikawa
  • Patent number: 9563128
    Abstract: New photoresist compositions are provided that are useful for immersion lithography. Preferred photoresist compositions of the invention comprise one or more materials that can be substantially non-mixable with a resin component of the resist. Further preferred photoresist compositions of the invention comprise 1) Si substitution, 2) fluorine substitution; 3) hyperbranched polymers; and/or 4) polymeric particles. 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: May 5, 2014
    Date of Patent: February 7, 2017
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventor: Deyan Wang
  • Patent number: 9563124
    Abstract: A photoresist composition comprising a resin which has no acid-labile group and which comprises a structural unit represented by formula (I); and a structural unit represented by formula (a4); a resin which has an acid-labile group; and an acid generator.
    Type: Grant
    Filed: July 24, 2013
    Date of Patent: February 7, 2017
    Assignee: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Tatsuro Masuyama, Satoshi Yamaguchi, Koji Ichikawa
  • Patent number: 9564339
    Abstract: Method of forming a protective hard mask layer on a substrate in a semiconductor etch process, comprising the step of applying by solution deposition on the substrate a solution or colloidal dispersion of an alumina polymer, said solution or dispersion being obtained by hydrolysis and condensation of monomers of at least one aluminum oxide precursor in a solvent or a solvent mixture in the presence of water and a catalyst. The invention can be used for making a hard mask in a TSV process to form a high aspect ratio via a structure on a semiconductor substrate.
    Type: Grant
    Filed: March 29, 2010
    Date of Patent: February 7, 2017
    Assignee: Pibond Oy
    Inventors: Juha T. Rantala, Thomas Gädda, Wei-Min Li, David A. Thomas, William McLaughlin
  • Patent number: 9557651
    Abstract: A chemically amplified positive-type photosensitive resin composition capable of suppressing the phenomenon of footing in which the width of the bottom (the side proximal to the surface of a support) becomes narrower than that of the top (the side proximal to the surface of a resist layer) when a resist pattern serving as a template for a plated article is formed on a metal surface of a substrate using the composition. A mercapto compound is contained in the composition which includes an acid generator capable of producing an acid when irradiated with an active ray or radiation and a resin whose solubility in alkali increases under the action of acid.
    Type: Grant
    Filed: March 19, 2015
    Date of Patent: January 31, 2017
    Assignee: TOKYO OHKA KOGYO CO., LTD.
    Inventors: Shota Katayama, Yasushi Washio, Takahiro Shimizu
  • Patent number: 9557645
    Abstract: A positive photosensitive resin composition containing a polymer compound obtained in the presence of an acid catalyst by condensation of at least a siloxane compound shown by formula (1), a phenol compounds shown by formula (2) and/or formula (3), and aldehydes and ketones shown by formula (4), a photosensitive material capable of generating an acid by light and increasing a dissolution rate in an aqueous alkaline solution, a crosslinker, and a solvent. There can be provided a positive photosensitive resin composition that can remedy the problem of delamination generated on metal wiring, electrode, and substrate such as Cu and Al, especially on substrate SiN, and can form fine pattern having forward tapered shape without generating scum and footing profile in the pattern bottom and on the substrate when the widely used 2.38% TMAH aqueous solution is used as a developer.
    Type: Grant
    Filed: June 1, 2015
    Date of Patent: January 31, 2017
    Assignee: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Katsuya Takemura, Masashi Iio, Hiroyuki Urano, Takashi Miyazaki
  • Patent number: 9557642
    Abstract: A photoresist composition includes a first polymer in which at least half of the repeat units are photoacid-generating repeat units, and a second polymer that exhibits a change in solubility in an alkali developer under the action of acid. In the first polymer, each of the photoacid-generating repeat units comprises photoacid-generating functionality and base-solubility-enhancing functionality.
    Type: Grant
    Filed: August 24, 2015
    Date of Patent: January 31, 2017
    Assignee: ROHM AND HAAS ELECTRONIC MATERIALS LLC
    Inventors: Paul J. LaBeaume, Vipul Jain, Suzanne M. Coley, James W. Thackeray, James F. Cameron, Amy M. Kwok, David A. Valeri
  • Patent number: 9557641
    Abstract: A photoresist composition containing: a polymer including an acid-labile group; a radiation-sensitive acid generator; and an acid diffusion control agent that contains a compound represented by a formula (1). In the formula (1), R1, R2 and R3 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms. A represents a group having a valency of n that is obtained by combining: a hydrogen atom, a linear hydrocarbon group having 1 to 30 carbon atoms, an alicyclic hydrocarbon group having 3 to 30 carbon atoms or a combination thereof; —O—, —CO—, —COO—, —SO2O—, —NRSO2—, —NRSO2O—, —NRCO— or a combination thereof; and n nitrogen atoms as a binding site to the carbonyl group in the formula (1), in which a sum of atomic masses of the atoms constituting A is no less than 120. n is an integer of 1 to 4.
    Type: Grant
    Filed: September 15, 2014
    Date of Patent: January 31, 2017
    Assignee: JSR CORPORATION
    Inventor: Hayato Namai
  • Patent number: 9551929
    Abstract: An androstane or estrane-substituted cholane as base resin is combined with an acid generator to formulate a positive resist composition, especially chemically amplified positive resist composition.
    Type: Grant
    Filed: October 30, 2015
    Date of Patent: January 24, 2017
    Assignee: SHIN-ETSU CHEMICAL CO., LTD.
    Inventor: Jun Hatakeyama
  • Patent number: 9551936
    Abstract: A method of modifying a surface of a photoresist material including exposing the photoresist material to an aqueous ionic surfactant solution and varying the pH of the aqueous ionic surfactant solution until a fluorochemical layer is formed in or on the photoresist material. The aqueous ionic surfactant solution includes a perfluoroalkyl sulfonamide the formula: RfS02NH—R? where Rf=CnF2n+1— and n=1 to 6, R?=—H, —CH3, and —CH2CH2OH. The aqueous ionic surfactant solution has a pH of within about 3 pH units of a pKa of the perfluoroalkyl sulfonamide.
    Type: Grant
    Filed: August 1, 2012
    Date of Patent: January 24, 2017
    Assignee: 3M INNOVATIVE PROPERTIES COMPANY
    Inventors: Jason M. Kehren, Patricia M. Savu, Matthew J. Pinnow
  • Patent number: 9547240
    Abstract: A resin comprising: a structural unit which has, at a side chain, a carbonyl group and a thiolactone ring-containing amino group where the thiolactone ring may have a substituent, and a structural unit having an acid-labile group.
    Type: Grant
    Filed: November 21, 2014
    Date of Patent: January 17, 2017
    Assignee: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Mitsuyoshi Ochiai, Koji Ichikawa, Masahiko Shimada
  • Patent number: 9547239
    Abstract: A positive photosensitive resin composition containing a polyimide resin that allows patterns to be satisfactorily formed by photolithography, and provides patterns with excellent heat resistance, and a method for forming polyimide resin patterns using the positive photosensitive resin composition. A patterned polyimide resin film formed by the method for forming polyimide resin patterns. To the photosensitive resin composition are added a polyimide resin, and a compound in which an imidazole compound having a specific structure is generated by the action of light.
    Type: Grant
    Filed: October 25, 2013
    Date of Patent: January 17, 2017
    Assignee: TOKYO OHKA KOGYO CO., LTD.
    Inventors: Kunihiro Noda, Hiroki Chisaka, Dai Shiota
  • Patent number: 9540550
    Abstract: The present invention provides a thermally conductive adhesive composition, based on the total weight of the composition, comprising: (a) 5-70% by weight of an epoxy component; (b) 5-60% by weight of thermally conductive material; (c) 0.001-10% by weight of a photoinitiator; (d) 0-40% by weight of a thermoplastic polymer; (e) 0-50% by weight of a hydroxyl-functional component; and (f) 0-50% by weight of a halogen-free flame retardant. The present invention further provides a thermally conductive adhesive tape comprising the adhesive composition.
    Type: Grant
    Filed: September 29, 2012
    Date of Patent: January 10, 2017
    Assignee: 3M INNOVATIVE PROPERTIES COMPANY
    Inventors: Qing Wu, Zhou Li, Liang Qin, Fanwang Kong, Hongmei Wan
  • Patent number: 9541831
    Abstract: A positive resist composition comprising: (A) a resin which comes to have an enhanced solubility in an alkaline developing solution by an action of an acid; (B) a compound which generates an acid upon irradiation with actinic rays or a radiation; (C) a fluorine-containing compound containing at least one group selected from the groups (x) to (z); and (F) a solvent, and a method of pattern formation with the composition: (x) an alkali-soluble group; (y) a group which decomposes by an action of an alkaline developing solution to enhance a solubility in an alkaline developing solution; and (z) a group which decomposes by an action of an acid.
    Type: Grant
    Filed: March 4, 2015
    Date of Patent: January 10, 2017
    Assignee: FUJIFILM Corporation
    Inventors: Hiromi Kanda, Shinichi Kanna, Haruki Inabe
  • Patent number: 9540476
    Abstract: Polymeric reaction products of certain aromatic alcohols with certain aromatic aldehydes are useful as underlayers in semiconductor manufacturing processes.
    Type: Grant
    Filed: December 12, 2014
    Date of Patent: January 10, 2017
    Assignees: Rohm and Haas Electronic Materials LLC, Rohm and Haas Electronic Materials Korea Ltd.
    Inventors: Li Cui, Sung Wook Cho, Mingqi Li, Shintaro Yamada, Peter Trefonas, III, Robert L. Auger
  • Patent number: 9541829
    Abstract: A photosensitive composition comprises a fluorinated solvent, a photo-acid generator and a copolymer. The copolymer comprises at least three distinct repeating units, including a first repeating unit having a fluorine-containing group, a second repeating unit having an acid-catalyzed cross-linkable group, and a third repeating unit having a sensitizing dye. The composition is useful in the fabrication of electronic devices, especially organic electronic and bioelectronic devices.
    Type: Grant
    Filed: July 18, 2014
    Date of Patent: January 10, 2017
    Assignee: Orthogonal, Inc.
    Inventors: Douglas Robert Robello, Charles Warren Wright
  • Patent number: 9540468
    Abstract: Provided is a resist copolymer which has favorable sensitivity, enables a resist pattern to be formed to have a favorable shape, has favorable dry etching resistance when a dry etching is carried out using the resist pattern as a mask, and suppresses the surface roughness of a pattern formed by carrying out a dry etching process to a substrate. A resist copolymer including a constituent unit (1) based on a (meth)acrylic acid ester derivative having a cyclic hydrocarbon group such as an adamantane ring and two or more cyano groups bonded to the cyclic hydrocarbon group, a constituent unit (2) having a lactone backbone and a cross-linking cyclic structure, and a constituent unit (3) having an acid leaving group.
    Type: Grant
    Filed: June 10, 2014
    Date of Patent: January 10, 2017
    Assignee: Mitsubishi Rayon Co., Ltd.
    Inventors: Keisuke Kato, Atsushi Yasuda, Ryuichi Ansai, Shinichi Maeda
  • Patent number: 9535325
    Abstract: The present invention provides the onium salt comprises the material represented by the following general formula (0-1), wherein Rf represents a fluorine atom or a trifluoromethyl group; Y represents a cyclic hydrocarbon group having 3 to 30 carbon atoms, the hydrogen atom in the cyclic hydrocarbon group may be substituted by a hetero atom itself or a monovalent hydrocarbon group which may be substituted by a hetero atom(s), and the hetero atom(s) may be interposed into the cyclic structure of the cyclic hydrocarbon group and the monovalent hydrocarbon group; and M+ represents a monovalent cation. There can be provided an onium salt which can improve resolution at the time of forming a pattern and give a pattern with less line edge roughness (LER) when it is used in a chemically amplified positive resist composition.
    Type: Grant
    Filed: December 17, 2014
    Date of Patent: January 3, 2017
    Assignee: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Daisuke Domon, Keiichi Masunaga, Satoshi Watanabe, Masahiro Fukushima, Koji Hasegawa
  • Patent number: 9535323
    Abstract: By a lithographic printing plate precursor including a support having provided thereon an image-recording layer capable of forming an image by supplying at least any of printing ink and dampening water on a printing machine after image exposure to remove an unexposed area thereof, wherein the image-recording layer contains an infrared absorbing agent, a polymerization initiator, a polymerizable compound and a polysaccharide having a sulfonic acid group or a group made by a salt thereof and a plate making method of a lithographic printing plate using the same, a lithographic printing plate precursor which exhibits good development property while maintaining printing durability of a lithographic printing plate after development and a plate making method of a lithographic printing plate using the same can be provided.
    Type: Grant
    Filed: March 25, 2015
    Date of Patent: January 3, 2017
    Assignee: FUJIFILM Corporation
    Inventor: Genki Takanashi
  • Patent number: 9527937
    Abstract: The present invention provides a polymer compound for a conductive polymer, containing one or more repeating units (a) represented by the following general formula (1), the polymer compound for a conductive polymer being synthesized by ion-exchange of a lithium salt, a sodium salt, a potassium salt, or a nitrogen compound salt of a sulfonic acid residue, and having a weight average molecular weight in the range of 1,000 to 500,000. There can be provided a polymer compound for a conductive polymer having a specific superacidic sulfo group which is soluble in an organic solvent, and suitably used for a fuel cell or a dopant for a conductive material.
    Type: Grant
    Filed: June 4, 2015
    Date of Patent: December 27, 2016
    Assignee: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Jun Hatakeyama, Koji Hasegawa, Takayuki Nagasawa, Masayoshi Sagehashi, Masaki Ohashi
  • Patent number: 9529259
    Abstract: A radiation-sensitive resin composition includes a polymer including a structural unit that includes an acid-labile group; and a compound represented by formula (1). R1 represents a monovalent organic group having 1 to 30 carbon atoms. L represents a single bond, an oxygen atom or a sulfur atom. M+ represents a monovalent radioactive ray-labile onium cation. The monovalent organic group represented by R1 is preferably a monovalent hydrocarbon group or a monovalent fluorinated hydrocarbon group, and L preferably represents a single bond. The monovalent organic group represented by R1 is preferably a monovalent hydrocarbon group, a monovalent fluorinated hydrocarbon group, a monovalent aliphatic heterocyclic group or a monovalent fluorinated aliphatic heterocyclic group, and L preferably represents an oxygen atom or a sulfur atom. The monovalent radioactive ray-labile onium cation represented by M+ is preferably represented by the formula (X).
    Type: Grant
    Filed: August 17, 2015
    Date of Patent: December 27, 2016
    Assignee: JSR CORPORATION
    Inventor: Hayato Namai
  • Patent number: 9527809
    Abstract: There is provided an actinic ray-sensitive or radiation-sensitive resin composition containing a compound represented by the following formula (1) or (2), and the formula (1) and (2) are defined as herein, and a resist film comprising the actinic ray-sensitive or radiation-sensitive resin composition, and a pattern forming method comprising a step of exposing the resist film, and a step of developing the exposed film, and a method for manufacturing an electronic device, comprising the pattern forming method, and an electronic device manufactured by the manufacturing method of an electronic device.
    Type: Grant
    Filed: September 29, 2015
    Date of Patent: December 27, 2016
    Assignee: FUJIFILM Corporation
    Inventors: Natsumi Yokokawa, Hiroo Takizawa, Shuji Hirano, Wataru Nihashi, Hideaki Tsubaki
  • Patent number: 9529265
    Abstract: Provided in one embodiment is a method that includes selecting a photoresist that is one of a positive-tone photoresist and a negative-tone photoresist. A first additive or a second additive is selected based on the photoresist. The first additive has a fluorine component and a base component attached to a polymer and is selected if the a positive-tone resist is provided. The second additive has the fluorine component and an acid component attached to the polymer and is selected with a negative-tone resist is provided. The selected photoresist and the selected additive material are applied to a target substrate.
    Type: Grant
    Filed: June 20, 2014
    Date of Patent: December 27, 2016
    Assignee: Taiwan Semiconductor Manufacturing Company, Ltd.
    Inventors: An-Ren Zi, Chen-Hau Wu, Ching-Yu Chang
  • Patent number: 9523917
    Abstract: Methods of forming patterns includes guide patterns on a neutral layer. A self-assembling block copolymer (BCP) layer on the guide patterns and the neutral layer. By annealing the self-assembling BCP layer, first polymer block domains and second polymer block domains are formed The guide patterns are formed of a developable antireflective material. The neutral layer is formed of a cross-linked polymeric material.
    Type: Grant
    Filed: April 25, 2016
    Date of Patent: December 20, 2016
    Assignee: SK Hynix Inc.
    Inventors: Keun Do Ban, Cheol Kyu Bok, Jung Gun Heo, Hong Ik Kim
  • Patent number: 9522998
    Abstract: Provided are: a resin mold material and a resin replica mold material composition for imprinting having a superior mold releasability; a resin mold and a resin replica mold resulting from containing the material composition; and a method for producing them. The resin mold material or resin replica mold material composition for imprinting contains 100 parts by weight of a mold resin or replica mold resin for imprinting and 0.1 to 10 parts by weight of a curable fluoropolymer (A). Preferably, the fluoropolymer (A) has a weight-average molecular weight of 3,000 to 20,000 and results from including as repeating units (a1) an ?-position substituted acrylate having a fluoroalkyl group having 4 to 6 carbon atoms and (a2) and 5 to 120 parts by weight of a high-softening-point monomer exhibiting a glass transition point or softening point of at least 50° C. in the homopolymer state.
    Type: Grant
    Filed: April 9, 2013
    Date of Patent: December 20, 2016
    Assignee: DAIKIN INDUSTRIES, LTD.
    Inventors: Tsuneo Yamashita, Masamichi Morita, Yoshiko Kuwajima
  • Patent number: 9522868
    Abstract: A tetrakis(ether-substituted formylphenyl) expressed by General Formula (1): wherein R1 represents an alkyl group with 1 to 8 carbon atoms or alkoxyl group with 1 to 8 carbon atoms, or aromatic hydrocarbon group or saturated hydrocarbon group with 1 to 8 carbon atoms having an aromatic hydrocarbon group, n represents 0 or an integer of 1 to 3, R2 represents a divalent monocyclic or fused-ring aromatic hydrocarbon group with 6 to 15 carbon atoms or divalent aliphatic hydrocarbon group with 1 to 8 carbon atoms that may have a monocyclic or fused-ring aromatic hydrocarbon group with 6 to 15 carbon atoms, R3 represents a hydrogen atom or alkyl group with 1 to 6 carbon atoms, A represents a tetravalent carbon atom group or tetravalent saturated hydrocarbon group with 2 or more carbon atoms, where, if A is a tetravalent saturated hydrocarbon group with 2 or more carbon atoms, the two carbon atoms in the A group are bonded with two phenyl groups, respectively.
    Type: Grant
    Filed: September 28, 2015
    Date of Patent: December 20, 2016
    Assignee: HONSHU CHEMICAL INDUSTRY CO., LTD.
    Inventors: Akira Yoshitomo, Tatsuya Iwai
  • Patent number: 9523914
    Abstract: A chemically amplified resist composition comprising a base polymer, an acid generator, and a basic compound which is a cholanoate having an acid labile group-protected amino group has a high contrast of alkaline dissolution rate before and after exposure and high resolution and forms a pattern of satisfactory profile with minimal roughness.
    Type: Grant
    Filed: November 17, 2015
    Date of Patent: December 20, 2016
    Assignee: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Jun Hatakeyama, Masaki Ohashi
  • Patent number: 9519216
    Abstract: The present disclosure relates to compositions that include at least one polybenzoxazole precursor polymer, at least one photoacid generator, and at least one basic compound. Articles, films, and methods related to these compositions are also disclosed.
    Type: Grant
    Filed: January 30, 2009
    Date of Patent: December 13, 2016
    Assignee: Fujifilm Electronic Materials U.S.A., Inc.
    Inventors: Ahmad A. Naiini, Il'ya Rushkin, William D. Weber, Donald W. Racicot
  • Patent number: 9519214
    Abstract: An actinic-ray- or radiation-sensitive resin composition includes a compound (A) that is configured to produce an acid when exposed to actinic rays or radiation, and a resin (B). The compound (A) is expressed by general formula (1) or (2) below. The resin (B) contains a repeating unit (b) containing a group that is configured to decompose when acted on by an acid to thereby produce an alcoholic hydroxyl group.
    Type: Grant
    Filed: August 5, 2015
    Date of Patent: December 13, 2016
    Assignee: FUJIFILM Corporation
    Inventor: Fumihiro Yoshino
  • Patent number: 9513547
    Abstract: The pattern forming method of the present invention includes (i) forming a film using an actinic ray-sensitive or radiation-sensitive resin composition which contains a resin (A) which has a repeating unit including a group capable of generating a polar group by being decomposed due to an action of an acid and a repeating unit including a carboxyl group, a compound (B) which generates an acid according to irradiation with actinic rays or radiation, and a solvent (C); (ii) exposing the film using a KrF excimer laser, extreme ultraviolet rays, or an electron beam; and (iii) forming a negative tone pattern by developing the exposed film using a developer which includes an organic solvent.
    Type: Grant
    Filed: January 28, 2015
    Date of Patent: December 6, 2016
    Assignee: FUJIFILM Corporation
    Inventors: Sou Kamimura, Hidenori Takahashi, Keita Kato
  • Patent number: 9514949
    Abstract: Whereas, conventionally, ashing had been used at the time of removal, the present invention provides a material for forming an organic hard mask that can be removed by an alkaline aqueous solution, and thus can be expected to reduce damage to the substrate at the time of the removal. A composition for forming an organic hard mask layer comprising: a polymer (A) including a structural unit of Formula (1) and a structural unit of Formula (2); a crosslinkable compound (B) including at least two of blocked isocyanate groups, methylol groups, or C1-5 alkoxymethyl groups; and a solvent (C), wherein an organic hard mask layer obtained from the composition for forming an organic hard mask layer is used at the lowest layer in a lithography process using a multi-layer film, wherein R1 to R4 have the same definition as ones in the specification.
    Type: Grant
    Filed: May 18, 2012
    Date of Patent: December 6, 2016
    Assignee: NISSAN CHEMICAL INDUSTRIES, LTD.
    Inventors: Yasunobu Someya, Yuki Usui, Masakazu Kato, Tetsuya Shinjo, Keisuke Hashimoto, Ryo Karasawa
  • Patent number: 9513548
    Abstract: A radiation-sensitive resin composition includes a first polymer including an acid-labile group, an acid generator to generate an acid upon exposure to radiation, and a second polymer including a fluorine atom and a functional group shown by a general formula (x). The second polymer has a fluorine atom content higher than a fluorine atom content of the first polymer. R1 represents an alkali-labile group. A represents an oxygen atom, —NR?—, —CO—O—# or —SO2—O—##, wherein the oxygen atom represented by A is not an oxygen atom bonded directly to an aromatic ring, a carbonyl group, or a sulfoxyl group, R? represents a hydrogen atom or an alkali-labile group, and “#” and “##” each indicate a bonding hand bonded to R1.
    Type: Grant
    Filed: April 2, 2014
    Date of Patent: December 6, 2016
    Assignee: JSR CORPORATION
    Inventors: Yuusuke Asano, Mitsuo Satou, Hiromitsu Nakashima, Kazuki Kasahara, Yoshifumi Oizumi, Masafumi Hori, Takanori Kawakami, Yasuhiko Matsuda, Kazuo Nakahara
  • Patent number: 9514950
    Abstract: Methods of increasing etch selectivity in imprint lithography are described which employ material deposition techniques that impart a unique morphology to the multi-layer material stacks, thereby enhancing etch process window and improving etch selectivity. For example, etch selectivity of 50:1 or more between patterned resist layer and deposited metals, metalloids, or non-organic oxides can be achieved, which greatly preserves the pattern feature height prior to the etch process that transfers the pattern into the substrate, allowing for sub-20 nm pattern transfer at high fidelity.
    Type: Grant
    Filed: December 30, 2014
    Date of Patent: December 6, 2016
    Assignees: Canon Nanotechnologies, Inc., Molecular Imprints, Inc.
    Inventors: Zhengmao Ye, Dwayne L. LaBrake
  • Patent number: 9507261
    Abstract: A photosensitive composition, a protective film, and an element having the protective film are provided. The photosensitive composition includes a polysiloxane (A), an o-naphthoquinonediazidesulfonate (B), and a solvent (C). The polysiloxane (A) is obtained by polycondensing a mixture, wherein the mixture includes a silane monomer (a-1) represented by formula (1), a silane monomer (a-2) represented by formula (2), and a silicon-containing compound (a-3). The silicon-containing compound (a-3) is selected from the group consisting of a silane monomer represented by formula (3), a siloxane prepolymer, and a silica particle. The photosensitive composition can be made into a protective film with excellent chemical resistance.
    Type: Grant
    Filed: April 30, 2015
    Date of Patent: November 29, 2016
    Assignee: Chi Mei Corporation
    Inventors: Wei-Jie Huang, Chun-An Shih
  • Patent number: 9507259
    Abstract: A photoresist composition comprises an acid-sensitive polymer, and a cyclic sulfonium compound having the formula: (Ra)1—(Ar)—S+(—CH2—)m·?O3S—(CRb2)n-(L)p-X wherein each Ra is independently a substituted or unsubstituted C1-30 alkyl group, C6-30 aryl group, C7-30 aralkyl group, or combination comprising at least one of the foregoing, Ar is a monocyclic, polycyclic, or fused polycyclic C6-30 aryl group, each Rb is independently H, F, a linear or branched C1-10 fluoroalkyl or a linear or branched heteroatom-containing C1-10 fluoroalkyl, L is a C1-30 linking group optionally comprising a heteroatom comprising O, S, N, F, or a combination comprising at least one of the foregoing heteroatoms, X is a substituted or unsubstituted, C5 or greater monocyclic, polycyclic or fused polycyclic cycloaliphatic group, optionally comprising a heteroatom comprising O, S, N, F, or a combination comprising at least one of the foregoing, and 1 is an integer of 0 to 4, m is an integer of 3 to 20, n is an integer of 0 to 4, and p
    Type: Grant
    Filed: May 29, 2012
    Date of Patent: November 29, 2016
    Assignee: ROHM AND HAAS ELECTRONIC MATERIALS LLC
    Inventors: Mingqi Li, Emad Aqad, Cong Liu, Ching-Lung Chen, Shintaro Yamada, Cheng-bai Xu, Joseph Mattia
  • Patent number: 9505948
    Abstract: A thermally decomposable polymer composition comprising a polyester containing repeating units of an ester of diglycolic acid and difunctional tertiary alcohol are disclosed, which are useful in the forming of microelectronic assemblies. A representative example of a composition comprises a thermally decomposable polymer of the formula: wherein n is at least about 20, which provides both tackiness and solder fluxing, among other benefits.
    Type: Grant
    Filed: December 12, 2013
    Date of Patent: November 29, 2016
    Assignee: PROMERUS, LLC
    Inventors: W. C. Peter Tsang, Andrew Bell, Hongshi Zhen, Keitaro Seto
  • Patent number: 9508553
    Abstract: New photoresists are provided that comprise a multi-keto component and that are particularly useful for ion implant lithography applications. Preferred photoresists of the invention can exhibit good adhesion to underlying inorganic surfaces such as SiON, silicon oxide, silicon nitride, hafnium silicate, zirconium silicate and other inorganic surfaces.
    Type: Grant
    Filed: December 30, 2011
    Date of Patent: November 29, 2016
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: Gerd Pohlers, Stefan J. Caporale
  • Patent number: 9507260
    Abstract: New photoresist compositions are provided that are useful for immersion lithography. In one preferred aspect, photoresist composition are provided that comprise: (i) one or more resins that comprise photoacid-labile groups, (ii) a photoactive component, and (iii) one or more materials that comprise photoacid labile groups and that are distinct from the one or more resins; wherein the deprotection activation energy of photoacid-labile groups of the one or more materials is about the same as or lower than the deprotection activation energy of photoacid-labile groups of the one or more resins. In another preferred aspect, photoresist compositions are provided that comprise (i) one or more resins, (ii) a photoactive component, and (iii) one or more materials that comprise a sufficient amount of acidic groups to provide a dark field dissolution rate of at least one angstrom per second.
    Type: Grant
    Filed: November 19, 2009
    Date of Patent: November 29, 2016
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: Deyan Wang, Chunyi Wu, Cheng-Bai Xu, George G. Barclay
  • Patent number: 9499646
    Abstract: A negative resist composition including a complex represented by the general formula (1); and a polymerization initiator, in which M represents hafnium (Hf) or zirconium (Zr), X represents a ligand comprising a conjugate base of an acid which has an acid dissociation constant (pKa) of 3.8 or less and has a polymerizable group, Y represents a ligand having no polymerizable group, and n represents an integer of 1 to 4.
    Type: Grant
    Filed: May 12, 2016
    Date of Patent: November 22, 2016
    Assignee: TOKYO OHKA KOGYO CO., LTD.
    Inventors: Naoki Yamashita, Yoshitaka Komuro, Yoshiyuki Utsumi, Daiju Shiono
  • Patent number: 9500947
    Abstract: Acid generator compounds are provided that are particularly useful as a photoresist composition component. Acid generator compounds of the invention comprise 1) a cyclic sulfonium salt and 2) a covalently linked photoacid-labile group. In one aspect, thioxanthone acid generator compounds are particularly preferred, including acid generator compounds that comprise (i) a thioxanthone moiety; and (ii) one or more covalently linked acid labile-groups.
    Type: Grant
    Filed: September 16, 2013
    Date of Patent: November 22, 2016
    Assignees: Rohm and Haas Electronic Materials LLC, Dow Global Technologies LLC
    Inventors: Paul J. LaBeaume, Aaron A. Rachford, Vipul Jain
  • Patent number: 9500950
    Abstract: An object of the present invention is to provide a novel fluorine-containing polymer, a radiation-sensitive resin composition for liquid immersion lithography which contains the fluorine-containing polymer, which leads to a pattern having an excellent shape and excellent depth of focus, wherein the amount of an eluted component in a liquid for liquid immersion lithography such as water that comes in contact with the resist during exposure in liquid immersion lithography is little, and which provides a larger receding contact angle between the resist film and the liquid for liquid immersion lithography such as water, and a method for purifying the fluorine-containing polymer. The present resin composition comprises a novel fluorine-containing polymer (A) containing repeating units represented by the general formulae (1) and (2) and having Mw of 1,000-50,000, a resin (B) having an acid-unstable group, a radiation-sensitive acid generator (C), a nitrogen-containing compound (D) and a solvent (E).
    Type: Grant
    Filed: November 5, 2015
    Date of Patent: November 22, 2016
    Assignee: JSR CORPORATION
    Inventors: Hiroki Nakagawa, Hiromitsu Nakashima, Gouji Wakamatsu, Kentarou Gotou, Yukio Nishimura, Takeo Shioya
  • Patent number: 9500948
    Abstract: A method of patterning a device comprises providing on a device substrate a layer of a fluorinated photopolymer comprising at least three distinct repeating units including a first repeating unit having a fluorine-containing group, a second repeating unit having an acid- or alcohol-forming precursor group, and a third repeating unit having a sensitizing dye. The photopolymer has a total fluorine content in a range of 15 to 60% by weight. The photopolymer layer is exposed to patterned light and contacted with a developing agent to remove a portion of exposed photopolymer layer in accordance with the patterned light, thereby forming a developed structure having a first pattern of photopolymer covering the substrate and a complementary second pattern of uncovered substrate corresponding to the removed portion of photopolymer. The developing agent comprises at least 50% by volume of a fluorinated solvent.
    Type: Grant
    Filed: May 30, 2014
    Date of Patent: November 22, 2016
    Assignee: Orthogonal, Inc.
    Inventors: Charles Warren Wright, Douglas Robert Robello
  • Patent number: 9488910
    Abstract: New bis(sulfonyl)imide and tri(sulfonyl)methide photoacid generator compounds (“PAGs”) are provided as well as photoresist compositions that comprise such PAG compounds.
    Type: Grant
    Filed: December 14, 2010
    Date of Patent: November 8, 2016
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: Cong Liu, Cheng-Bai Xu
  • Patent number: 9487665
    Abstract: An object of the present invention is to provide: a pigment dispersion liquid for inkjet ink, which is stable for a long period of storage and which increases repellency to ink ejection surface. Disclosed is a pigment dispersion liquid for inkjet ink, comprising: a pigment; a pigment dispersing agent; and a compound having an ethylenically unsaturated double bond, wherein the pigment dispersing agent has an amine value of 20 mgKOH/g or less and an acid value of 10 mgKOH/g or less, contains one or more components selected from the group consisting of: a copolymer having a styrene-derived repeating unit, a repeating unit derived from an unsaturated fatty acid having 12 or more carbon atoms, and a repeating unit derived from a polyalkylene oxide having an ethylenically unsaturated double bond; a specific salt of the copolymer and an amine derivative of the copolymer.
    Type: Grant
    Filed: February 5, 2013
    Date of Patent: November 8, 2016
    Assignee: DNP FINE CHEMICALS CO., LTD.
    Inventors: Yukiko Ishima, Keishiro Yoshimori, Yukio Sugita
  • Patent number: 9482949
    Abstract: A positive resist composition is provided comprising a polymer comprising recurring units having a carboxyl or phenolic hydroxyl group substituted with an acid labile group and recurring units of isosorbide nitrate ester, and having a Mw of 1,000-500,000. The resist composition has a satisfactory effect of suppressing acid diffusion and a high resolution, and forms a pattern of good profile and minimal edge roughness after exposure.
    Type: Grant
    Filed: January 14, 2015
    Date of Patent: November 1, 2016
    Assignee: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Jun Hatakeyama, Koji Hasegawa
  • Patent number: 9482953
    Abstract: A lithography apparatus and a method of using the same, the apparatus including a stage for accommodating a substrate that has a photoresist film thereon; a main unit on the stage, the main unit being configured to irradiate a projection beam to the photoresist film; and an electric field unit adjacent to the stage, the electric field unit being configured to apply an electric field to the photoresist film, wherein the electric field unit is configured to be turned on at a same time as or before irradiation of the projection beam, and is configured to be turned off at a same time as or after termination of the projection beam.
    Type: Grant
    Filed: February 11, 2014
    Date of Patent: November 1, 2016
    Assignee: SAMSUNG ELECTRONICS CO., LTD.
    Inventors: Cha-Won Koh, Jeon-Il Lee, Su-Min Kim, Hyun-Woo Kim, Jin Park
  • Patent number: 9482948
    Abstract: Provided are photoresist compositions useful in forming photolithographic patterns by a negative tone development process. Also provided are methods of forming photolithographic patterns by a negative tone development process and substrates coated with the photoresist compositions. The compositions, methods and coated substrates find particular applicability in the manufacture of semiconductor devices.
    Type: Grant
    Filed: October 22, 2015
    Date of Patent: November 1, 2016
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: Young Cheol Bae, Deyan Wang, Thomas Cardolaccia, Seokho Kang, Rosemary Bell
  • Patent number: 9477150
    Abstract: Novel photoacid generator compounds are provided. Photoresist compositions that include the novel photoacid generator compounds are also provided. The invention further provides methods of making and using the photoacid generator compounds and photoresist compositions disclosed herein. The compounds and compositions are useful as photoactive components in chemically amplified resist compositions for various microfabrication applications.
    Type: Grant
    Filed: March 13, 2015
    Date of Patent: October 25, 2016
    Assignee: HERAEUS PRECIOUS METALS NORTH AMERICA DAYCHEM LLC
    Inventors: Yongqiang Zhang, Daniel Greene, Ram B. Sharma
  • Patent number: 9475763
    Abstract: New nitrogen-containing compounds are provided that comprise multiple hydroxyl moieties and photoresist compositions that comprise such nitrogen-containing compounds. Preferred nitrogen-containing compounds comprise 1) multiple hydroxyl substituents (i.e. 2 or more) and 2) one or more photoacid-labile groups.
    Type: Grant
    Filed: January 5, 2015
    Date of Patent: October 25, 2016
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: Cong Liu, Chunyi Wu, Gerhard Pohlers, Gregory P. Prokopowicz, Cheng-Bai Xu