Pattern Elevated In Radiation Unexposed Areas Patents (Class 430/326)
  • Patent number: 8808959
    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: November 10, 2009
    Date of Patent: August 19, 2014
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hideo Hada, Yoshiyuki Utsumi, Takehiro Seshimo, Akiya Kawaue
  • Patent number: 8802347
    Abstract: Coating compositions include a polymer including: wherein R1 is a silicon containing moiety, R2 is an acid stable lactone functionality, and R3 is an acid labile lactone functionality; X1, X2, X3 are independently H or CH3; and m and o are non-zero positive integers and n is zero or a positive integer representing the number of repeat units; a photoacid generator; and a solvent. Also disclosed are methods for forming a pattern in the coating composition containing the same.
    Type: Grant
    Filed: November 6, 2009
    Date of Patent: August 12, 2014
    Assignee: International Business Machines Corporation
    Inventors: Robert D. Allen, Phillip J. Brock, Kuang-Jung Chen, Alexander Friz, Wu-Song Huang, Ratnam Sooriyakumaran, Sally A. Swanson, Hoa D. Truong
  • Patent number: 8802354
    Abstract: A photoresist material having a polymer that turns soluble to a base solution in response to reaction with acid. The material includes a photo-acid generator (PAG) that decomposes to form acid in response to radiation energy and a quencher capable of neutralizing acid and having a reduced mobility. The photoresist material can thereby prevent water mark defects from immersion lithography.
    Type: Grant
    Filed: April 5, 2013
    Date of Patent: August 12, 2014
    Assignee: Taiwan Semiconductor Manufacturing Company, Ltd.
    Inventor: Ching-Yu Chang
  • Patent number: 8802353
    Abstract: A radiation-sensitive composition containing 1 to 80% by weight of a solid component and 20 to 99% by weight of a solvent. The solid component contains a compound B which has (a) a structure derived from a polyphenol compound A by introducing an acid-dissociating group to at least one phenolic hydroxyl group of the polyphenol compound A which is synthesized by a condensation between a di- to tetrafunctional aromatic ketone or aromatic aldehyde each having 5 to 36 carbon atoms with a compound having 1 to 3 phenolic hydroxyl groups and 6 to 15 carbon atoms, and (b) a molecular weight of 400 to 2000. The composition containing the compound B is useful as an acid-amplified, non-polymeric resist material, because it is highly sensitive to radiation such as KrF excimer lasers, extreme ultraviolet rays, electron beams, and X-rays, and provides resist patterns with a high resolution, high heat resistance, and high etching resistance.
    Type: Grant
    Filed: September 13, 2012
    Date of Patent: August 12, 2014
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Masatoshi Echigo, Dai Oguro
  • Patent number: 8802348
    Abstract: A radiation-sensitive resin composition includes (A) an acid labile group-containing resin which becomes alkali-soluble by an action of an acid, (B) a radiation-sensitive acid generator, and (C) a solvent. The resin (A) includes repeating units shown by formulas (1) and (2), wherein R1 and R2 represent a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, R3 represents a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, X represents a hydrogen atom, a hydroxyl group, or an acyl group, m represents an integer from 1 to 18, and n represents an integer from 4 to 8.
    Type: Grant
    Filed: February 7, 2010
    Date of Patent: August 12, 2014
    Assignee: JSR Corporation
    Inventors: Noboru Otsuka, Takanori Kawakami, Yukio Nishimura, Makoto Sugiura
  • Patent number: 8802349
    Abstract: Provided is an actinic ray-sensitive or radiation-sensitive resin composition including: (A) a resin capable of increasing the solubility in an alkali developer by the action of an acid, the resin containing (a) a repeating unit represented by the following formula (AN-01), (B) a compound capable of generating an acid upon irradiation with an actinic ray or radiation, and (C) a resin that contains at least either a fluorine atom or a silicon atom and contains a repeating unit having a group capable of decomposing by the action of an alkali developer to increase the solubility in an alkali developer: wherein the variables in formula (AN-01) are defined in the description.
    Type: Grant
    Filed: March 31, 2010
    Date of Patent: August 12, 2014
    Assignee: FUJIFILM Corporation
    Inventors: Masahiro Yoshidome, Shuji Hirano, Hiroshi Saegusa, Kaoru Iwato, Yusuke Iizuka
  • Patent number: 8802351
    Abstract: A water dispersible composition comprises a polyaniline copolymer having a weight average molecular weight of at least 30,000 and a polymeric acid comprising sulfonic acid groups. The polyaniline copolymer comprises i) about 10 mol % to about 15 mol % of a fluorine-containing first aniline repeat unit based on total moles of repeat units in the polyaniline copolymer, and ii) a second aniline repeat unit comprising no fluorine. The sulfonic acid groups of the polymeric acid are present in a molar amount greater than or equal to total moles of repeat units of the polyaniline copolymer. The composition has a conductivity of at least 0.0001 S/cm.
    Type: Grant
    Filed: July 31, 2012
    Date of Patent: August 12, 2014
    Assignees: International Business Machines Corporation, Shin-Etsu Chemical Co. Ltd.
    Inventors: Luisa Dominica Bozano, Takayuki Nagasawa, Mark Hull Sherwood, Ratnam Sooriyakumaran, Linda Karin Sundberg, Satoshi Watanabe
  • Patent number: 8802352
    Abstract: A salt represented by formula (I): wherein Q1, Q2, L1, W, and Z+are defined in the specification.
    Type: Grant
    Filed: August 6, 2012
    Date of Patent: August 12, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Yuichi Mukai, Isao Yoshida
  • Patent number: 8795946
    Abstract: Polymerizable ester compounds having formula (1) are novel wherein R1 is H, F, methyl or trifluoromethyl, R2 is an acid labile group, Aa is a divalent hydrocarbon group which may be separated by —O— or —C(?O)—, and k1 is 0 or 1. They are useful as monomers to produce polymers which are transparent to radiation ?500 nm. Radiation-sensitive resist compositions comprising the polymers as base resin exhibit excellent developed properties.
    Type: Grant
    Filed: July 13, 2012
    Date of Patent: August 5, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Koji Hasegawa, Masayoshi Sagehashi, Yuuki Suka, Masashi Ilo
  • Patent number: 8795945
    Abstract: An actinic ray-sensitive or radiation-sensitive resin composition, and a resist film and a pattern forming method using the composition are provided, the composition including (A) a compound capable of decomposing by the action of an acid to increase the solubility of the resin (A) in an alkali developer; (B) a compound capable of generating an acid upon irradiation with an actinic ray or radiation; (C) a basic compound; and (D) a specific compound containing at least two specific alicyclic hydrocarbon groups each substituted with a hydroxyl group.
    Type: Grant
    Filed: March 4, 2011
    Date of Patent: August 5, 2014
    Assignee: FUJIFILM Corporation
    Inventors: Kana Fujii, Takamitsu Tomiga, Toru Fujimori
  • Patent number: 8795944
    Abstract: Provided is an actinic ray-sensitive or radiation-sensitive resin composition including: (A) a resin capable of increasing the solubility in an alkali developer by the action of an acid, (B) a compound capable of generating an acid upon irradiation with an actinic ray or radiation, and (C) a resin which contains (c) a repeating unit having at least one polarity conversion group and has at least either a fluorine atom or a silicon atom.
    Type: Grant
    Filed: December 11, 2009
    Date of Patent: August 5, 2014
    Assignee: FUJIFILM Corporation
    Inventors: Hiroshi Saegusa, Kaoru Iwato, Shuji Hirano, Yusuke Iizuka
  • Patent number: 8795942
    Abstract: There is disclosed a resist composition that remarkably improves the resolution of photolithography using a high energy beam such as ArF excimer laser light as a light source, and exhibits excellent resistance to surface roughness and side lobe under use of a halftone phase shift mask; and a patterning process using the resist composition. The positive resist composition at least comprises (A) a resin component comprising a repeating unit represented by the following general formula (1); (B) a photoacid generator generating sulfonic acid represented by the following general formula (2) upon exposure to a high energy beam; and (C) an onium salt where a cation is sulfonium represented by the following general formula (3), or ammonium represented by the following general formula (4); and an anion is represented by any one of the following general formulae (5) to (7).
    Type: Grant
    Filed: December 11, 2007
    Date of Patent: August 5, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Tomohiro Kobayashi, Youichi Ohsawa, Ryosuke Taniguchi
  • Patent number: 8790868
    Abstract: A method of forming a resist pattern, the method including: forming a resist film on a substrate using a resist composition containing a base component (A) that exhibits reduced solubility in an organic solvent under the action of acid, an acid generator component (B) that generates acid upon exposure and a fluorine-containing polymeric compound (F), exposing the resist film, and patterning the resist film by negative tone development using a developing solution containing the organic solvent, thereby forming a resist pattern, wherein the base component (A) contains a resin component (A1) containing a structural unit (a1) derived from an acrylate ester, the dissolution rates of (A1) and (F) in the developing solution are each at least 10 nm/s, and the absolute value of the difference in the dissolution rates of (A1) and (F) in the developing solution is not more than 80 nm/s.
    Type: Grant
    Filed: April 26, 2012
    Date of Patent: July 29, 2014
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hiroaki Shimizu, Hideto Nito
  • Patent number: 8790861
    Abstract: A monomer has the Formula I: wherein R1, R2, and R3 are each independently a C1-30 monovalent organic group, and R1, R2, and R3 are each independently unsubstituted or include a halogen, nitrile, ether, ester, ketone, alcohol, or a combination comprising at least one of the foregoing functional groups; R4 includes H, F, C1-4 alkyl, or C1-4 fluoroalkyl; A is a single bond or a divalent linker group, wherein A is unsubstituted or substituted to include a halogen, nitrile, ether, ester, ketone, alcohol, or a combination comprising at least one of the foregoing functional groups; m and n are each independently an integer of 1 to 8; and x is 0 to 2n+2, and y is 0 to 2m+2.
    Type: Grant
    Filed: December 21, 2012
    Date of Patent: July 29, 2014
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: Cong Liu, Mingqi Li, Cheng-Bai Xu
  • Patent number: 8791288
    Abstract: An acid-labile ester monomer of spirocyclic structure has formula (1) wherein Z is a monovalent group having a polymerizable double bond, X is a divalent group which forms a cyclopentane, cyclohexane or norbornane ring, R2 is H or monovalent hydrocarbon, R3 and R4 are H or monovalent hydrocarbon, or R3 and R4, taken together, stand for a divalent group which forms a cyclopentane or cyclohexane ring, and n is 1 or 2. A polymer obtained from the acid-labile ester monomer has so high reactivity in acid-catalyzed elimination reaction that the polymer may be used to formulate a resist composition having high resolution.
    Type: Grant
    Filed: May 25, 2010
    Date of Patent: July 29, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takeshi Kinsho, Tomohiro Kobayashi, Masayoshi Sagehashi, Takeru Watanabe, Koji Hasegawa, Seiichiro Tachibana
  • Patent number: 8785105
    Abstract: A sulfonium salt having a 4-fluorophenyl group is introduced as recurring units into a polymer comprising hydroxyphenyl (meth)acrylate units and acid labile group-containing (meth)acrylate units to form a polymer which is useful as a base resin in a resist composition. The resist composition has a high sensitivity, high resolution and minimized LER.
    Type: Grant
    Filed: November 9, 2011
    Date of Patent: July 22, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Masaki Ohashi, Seiichiro Tachibana, Jun Hatakeyama
  • Patent number: 8785104
    Abstract: A resist composition and a pattern forming method using the composition are provided, the resist composition including: (A) a resin that decomposes by an action of an acid to increase a solubility of the resin (A) in an alkali developer; (B) a compound capable of generating an acid upon irradiation with actinic rays or radiation; (C) a compound represented by formula (C1); and (D) a solvent: wherein n represents an integer of 1 to 6; w represents an integer of 1 to 6; p represents an integer of 1 to 6; m represents an integer of 1 to 6; Ra, Rb, Rc and Rd each independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or an aralkyl group, provided that Ra and Rb may combine together to form a ring, and Rc and Rd may combine together to form a ring.
    Type: Grant
    Filed: March 13, 2009
    Date of Patent: July 22, 2014
    Assignee: FUJIFILM Corporation
    Inventors: Kazuyoshi Mizutani, Jiro Yokoyama, Shinichi Sugiyama
  • Patent number: 8785106
    Abstract: A resist composition including: a base component (A) that exhibits changed solubility in a developing solution by the action of acid; a photoreactive quencher (C); and an acid generator component (B) that generates acid upon exposure, wherein the photoreactive quencher (C) contains a compound (C) represented by general formula (c1) shown below. In the formula, X represents a cyclic group of 3 to 30 carbon atoms which may have a substituent; R1 represents a divalent linking group; R2 represents an arylene group which may have a substituent, and each of R3 and R4 independently represents an aryl group which may have a substituent; R3 and R4 may be mutually bonded with the sulfur atom to form a ring; R5 represents a hydroxy group, a halogen atom, an alkyl group of 1 to 5 carbon atoms, an alkoxy group or a fluorinated alkyl group; p represents an integer of 0 to 2; and q represents an integer of 0 to 3.
    Type: Grant
    Filed: February 21, 2013
    Date of Patent: July 22, 2014
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Yoshitaka Komuro, Toshiaki Hato
  • Publication number: 20140199637
    Abstract: A pattern is formed by coating a first chemically amplified positive resist composition comprising a resin comprising recurring units having an acid labile group so that it may turn soluble in alkaline developer upon elimination of the acid labile group, a photoacid generator, and a first organic solvent, onto a processable substrate, prebaking, exposing, PEB, and developing in an alkaline developer to form a positive pattern; heating the positive pattern to render it resistant to a second organic solvent used in a second resist composition; coating the second resist composition, prebaking, exposing, PEB, and developing in a third organic solvent to form a negative pattern. The positive pattern and the negative pattern are simultaneously formed.
    Type: Application
    Filed: December 13, 2013
    Publication date: July 17, 2014
    Applicant: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Jun Hatakeyama, Kazuhiro Katayama
  • Patent number: 8778594
    Abstract: A resist composition having a resin having a structural unit represented by the formula (I), a resin being insoluble or poorly soluble in alkali aqueous solution, but becoming soluble in an alkali aqueous solution by the action of an acid and not including the structural unit represented by the formula (I), an acid generator, and a compound represented by the formula (II), wherein R1, A1, A13, A14, X12, R23, R24, R25, R26, X21 and X22 are defined in the specification.
    Type: Grant
    Filed: July 18, 2012
    Date of Patent: July 15, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Hiromu Sakamoto, Yuichi Mukai
  • Patent number: 8778592
    Abstract: A positive resist composition based on a polymer comprising recurring units of (meth)acrylate having a cyclic acid labile group and a dihydroxynaphthalene novolak resin, and containing a photoacid generator is improved in resolution, step coverage and adhesion on a highly reflective stepped substrate, has high resolution, and forms a pattern of good profile and minimal edge roughness through exposure and development.
    Type: Grant
    Filed: February 24, 2012
    Date of Patent: July 15, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Takeshi Nagata, Taku Morisawa
  • Patent number: 8778595
    Abstract: A resist composition containing a base component (A) which generates acid upon exposure, and exhibits changed solubility in a developing solution under the action of acid, wherein the base component (A) contains a polymeric compound (A1) having a structural unit (a5) represented by general formula (a5-0) shown below and a structural unit (a6) that generates acid upon exposure. In the formula, R represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms, R1 represents a sulfur atom or an oxygen atom, R2 represents a single bond or a divalent linking group, and Y represents a hydrocarbon group in which a carbon atom or a hydrogen atom may be substituted with a substituent.
    Type: Grant
    Filed: November 16, 2012
    Date of Patent: July 15, 2014
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Daichi Takaki, Daiju Shiono, Yoshiyuki Utsumi, Jun Iwashita
  • Publication number: 20140193749
    Abstract: A pattern-forming method includes in this order: step (1) of forming a film with an electron beam-sensitive or extreme ultraviolet radiation-sensitive resin composition that contains (A) a resin having an acid-decomposable repeating unit and capable of decreasing a solubility of the resin (A) in a developer containing an organic solvent by an action of an acid, (B) a compound capable of generating an acid upon irradiation with an electron beam or extreme ultraviolet radiation and (C) a solvent; step (2) of exposing the film with an electron beam or extreme ultraviolet radiation; and step (4) of forming a negative pattern by development of the film with a developer containing an organic solvent after the exposing of the film, wherein a content of the compound (B) is 21% by mass to 70% by mass on the basis of all solids content of the composition.
    Type: Application
    Filed: March 13, 2014
    Publication date: July 10, 2014
    Applicant: FUJIFILM CORPORATION
    Inventors: Hiroo TAKIZAWA, Hideaki TSUBAKI, Shuji HIRANO
  • Patent number: 8771916
    Abstract: An actinic ray-sensitive or radiation-sensitive resin composition, includes: (A) a resin capable of increasing the solubility of the resin (A) in an alkali developer by the action of an acid; and (C) a resin having at least either a fluorine atom or a silicon atom and containing (c) a repeating unit having at least two or more polarity conversion groups.
    Type: Grant
    Filed: December 11, 2009
    Date of Patent: July 8, 2014
    Assignee: FUJIFILM Corporation
    Inventors: Shuji Hirano, Kaoru Iwato, Hiroshi Saegusa, Yusuke Iizuka
  • Patent number: 8771907
    Abstract: According to one embodiment, a positive photosensitive resin composition includes a resin containing a specified acrylic acid besed-structural unit which generates a carboxyl group when its dissociative group is dissociated, which resin is insoluble in alkali or sparingly soluble in alkali but when its acid-dissociative group is dissociated, becomes soluble in alkali, a resin containing a structural unit derived from a radical-polymerizable monomer containing an epoxy group, a compound containing two or more epoxy groups in its molecule, provided that the resin containing the structural unit derived from a radical-polymerizable monomer containing an epoxy group is not included in this compound, and a compound that when exposed to actinic rays of 300 nm or longer wavelength, generates an acid.
    Type: Grant
    Filed: September 27, 2010
    Date of Patent: July 8, 2014
    Assignee: FUJIFILM Corporation
    Inventor: Satoshi Takita
  • Patent number: 8771917
    Abstract: Provided are (meth)acrylate monomers containing acetal moieties, polymers containing a unit formed from such a monomer and photoresist compositions containing such a polymer. The monomers, polymers and photoresist compositions are useful in forming photolithographic patterns. Also provided are substrates coated with the photoresist compositions, methods of forming photolithographic patterns and electronic devices. The compositions, methods and coated substrates find particular applicability in the manufacture of semiconductor devices.
    Type: Grant
    Filed: December 31, 2011
    Date of Patent: July 8, 2014
    Assignees: Rohm and Haas Electronics Materials LLC, Dow Global Technologies LLC
    Inventors: Matthias S. Ober, Young Cheol Bae, Yi Liu, Seung-Hyun Lee, Jong Keun Park
  • Patent number: 8765358
    Abstract: A water-soluble resin composition for forming fine patterns comprising water-soluble polymer represented by Chemical Formula 1 as below and the first water-soluble solvent, is coated and heated on a photoresist layer having at least one contact hole to reduce a size of the at least one contact hole. (In Chemical Formula 1, each of R1, R2, R3 and R5 independently represents an alkyl group of C1-30 or an cyclo alkyl group of C3-30 which respectively have one selected from the group consisting of hydrogen, an ether group, an ester group, a carbonyl group, an acetal, an epoxy group, a nitril group, an amine group, and an aldehyde group; each of R4, R6, R7 and R8 independently represents hydrogen or a methyl group; n represents an integer of 0 to 5; a represents a real number of 0.05 to 0.5; each of b, c and d respectively represents a real number of 0 to 0.7; and a+b+c+d=1).
    Type: Grant
    Filed: June 29, 2011
    Date of Patent: July 1, 2014
    Assignee: Korea Kumho Petrochemical Co., Ltd.
    Inventors: Sang Wook Park, So Jung Park, Dong-Chul Seo
  • Patent number: 8765357
    Abstract: The present invention provides a resin comprising a structural unit derived from a compound represented by the formula (I): wherein R1 represents a hydrogen atom or a methyl group, A2 represents a divalent fluorine-containing C1-C12 hydrocarbon group, and A1 represents a group represented by the formula (a-g1): A10-X10sA11-??(a-g1) wherein A10 is independently in each occurrence a C1-C5 aliphatic hydrocarbon group, A11 represents a C1-C5 aliphatic hydrocarbon group, X10 is independently in each occurrence —O—, —CO—, —CO—O— or —O—CO—, and s represents an integer of 0 to 2, and a photoresist composition comprising the resin and an acid generator.
    Type: Grant
    Filed: April 16, 2012
    Date of Patent: July 1, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tatsuro Masuyama, Koji Ichikawa
  • Patent number: 8765356
    Abstract: A molecular glass compound includes (A) a tetrameric reaction product of a specific aromatic compound having at least one hydroxy group, and a specific polycyclic or fused polycyclic aromatic aldehyde; and (B) an acid-removable protecting group as an adduct with the hydroxy group of the aromatic compound and/or a hydroxy group of the polycyclic or fused polycyclic aromatic aldehyde. A photoresist composition including the molecular glass compound, and a coated substrate including a layer of the photoresist composition are also disclosed.
    Type: Grant
    Filed: September 21, 2012
    Date of Patent: July 1, 2014
    Assignees: Dow Global Technologies LLC, Rohm and Haas Electronics Materials LLC
    Inventors: D. Patrick Green, Vipul Jain, Brad C. Bailey
  • Patent number: 8765355
    Abstract: A radiation sensitive resin composition includes a first polymer having a group represented by a following formula (1), and a radiation sensitive acid generator. n is an integer of 2 to 4. X represents a single bond or a bivalent organic group. A represents a (n+1) valent linking group. Each Q independently represents a group that includes an alkali-dissociable group.
    Type: Grant
    Filed: April 27, 2012
    Date of Patent: July 1, 2014
    Assignee: JSR Corporation
    Inventors: Takakazu Kimoto, Mitsuo Sato, Yusuke Asano, Tomohiro Kakizawa
  • Patent number: 8765352
    Abstract: A positive resist composition including a base component (A) which exhibits changed solubility in an alkali developing solution under the action of acid and an acid-generator component (B) which generates acid upon exposure, wherein the acid-generator component (B) includes an acid generator (B1) containing a compound represented by general formula (b1-1) shown below (wherein Z+ represents an organic cation).
    Type: Grant
    Filed: September 1, 2011
    Date of Patent: July 1, 2014
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Yoshiyuki Utsumi, Takehiro Seshimo
  • Patent number: 8758978
    Abstract: A radiation-sensitive resin composition includes a first polymer, a second polymer and a radiation-sensitive acid generator. The first polymer includes a repeating unit (I) shown by the following general formula (1), a fluorine atom in a molecule of the first polymer. The second a polymer includes an acid-labile group, and is insoluble or scarcely soluble in an alkali. R1 represents a hydrogen atom or the like, each of X1 and R2 represents a single bond or the like, R3 represents a hydrogen atom or the like, and R4 represents an acid-labile group.
    Type: Grant
    Filed: March 12, 2012
    Date of Patent: June 24, 2014
    Assignee: JSR Corporation
    Inventors: Mitsuo Satou, Tomohiro Kakizawa
  • Publication number: 20140170563
    Abstract: The invention provides a positive resist composition, wherein a polymer compound having the weight-average molecular weight in the range of 1,000 to 500,000 and comprising a repeating unit having a hydrogen atom in a carboxyl group and/or in a phenolic hydroxy group therein been substituted by an acid-labile group and a repeating unit “a” having a cyclopentadienyl complex shown by the following general formula (1) is used as a base resin therein. There can be a positive resist composition having not only small edge roughness (LER and LWR) while having a higher resolution than conventional positive resist compositions, but also a good pattern form after exposure and an extremely high etching resistance, especially a positive resist composition using a polymer compound suitable as a base resin for a chemically amplifying resist composition; and a patterning process.
    Type: Application
    Filed: November 20, 2013
    Publication date: June 19, 2014
    Applicant: SHIN-ETSU CHEMICAL CO., LTD.
    Inventor: Jun HATAKEYAMA
  • Patent number: 8753790
    Abstract: Embodiments in accordance with the present invention encompass self-imageable film forming compositions that comprise norbornene-type polymers and that can be formulated to be either positive tone imaging or negative tone. The films formed thereby are useful in the forming of microelectronic and optoelectronics devices.
    Type: Grant
    Filed: June 30, 2010
    Date of Patent: June 17, 2014
    Assignee: Promerus, LLC
    Inventors: Osamu Onishi, Haruo Ikeda, Larry Rhodes, Paul Evans, Edmund Elce, Andrew Bell, Chad Brick, Hendra Ng, Pramod Kandanarachchi
  • Patent number: 8753795
    Abstract: The present invention provides a photoresist composition containing: a resin which contains a structural unit derived from a compound having an acid-labile group and which is insoluble or poorly soluble in an alkali aqueous solution but becomes soluble in an alkali aqueous solution by the action of an acid; an acid generator and a compound represented by the formula (I): wherein R1, X1, R2, u1, s1, t1 are each defined in the specification, with the proviso that sum of s1 and t1 is 1 or 2.
    Type: Grant
    Filed: March 23, 2012
    Date of Patent: June 17, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Hiromu Sakamoto, Yuichi Mukai
  • Patent number: 8753796
    Abstract: The present invention provides a photoresist composition comprising a salt represented by the formula (I): wherein R1 and R2 independently each represent a fluorine atom or a C1-C6 perfluoroalkyl group, X1 represents a C1-C17 divalent saturated hydrocarbon group, etc., s1 represents 1 or 2, and t1 represents 0 or 1, with proviso that sum of s1 and t1 is 1 or 2, R3 represents a C1-C12 saturated hydrocarbon group, etc., u1 represents an integer of 0 to 8, and (Z1)+ represents an organic cation, a salt represented by the formula (II-0): wherein R4 represents a C1-C24 hydrocarbon group etc., X2 represents a C1-C6 alkanediyl group etc., and (Z2)+ represents an organic cation, and a resin being insoluble or poorly soluble in an aqueous alkali solution but becoming soluble in an aqueous alkali solution by the action of an acid.
    Type: Grant
    Filed: April 10, 2012
    Date of Patent: June 17, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Hiromu Sakamoto, Yuichi Mukai
  • Patent number: 8753792
    Abstract: A positive photosensitive composition comprising: (A) a compound capable of generating an acid upon irradiation with actinic rays or radiation; (B1) a resin of which solubility in an alkali developer increases under an action of an acid; and (B2) a resin that has at least one group selected from (a) an alkali-soluble group and (b) a group capable of decomposing under an action of an alkali to produce an alkali-soluble group, and the resin (B2) does not have a group capable of decomposing under an action of an acid; and a pattern forming method using the same.
    Type: Grant
    Filed: October 29, 2010
    Date of Patent: June 17, 2014
    Assignee: FUJIFILM Corporation
    Inventors: Kunihiko Kodama, Fumiyuki Nishiyama
  • Publication number: 20140162178
    Abstract: There is provided a photosensitive composition for forming a black matrix including pigment of 5˜20 wt %; binder resin of 1˜25 wt %; photo-polymerizable monomer of 1˜25 wt %; photopolymerization initiator of 1˜25 wt %; solvent of 65˜85 wt %; and photo base generator of 1˜10 wt %, based on 100 parts by weight of the photosensitive composition.
    Type: Application
    Filed: December 4, 2013
    Publication date: June 12, 2014
    Applicant: LG DISPLAY CO., LTD.
    Inventor: Youn-Sung NA
  • Publication number: 20140162188
    Abstract: A positive resist composition is provided comprising a polymer comprising recurring styrene units having an ester group bonded to a CF3—C(OH)—R3 group (R3?H, CH3, or CF3) such as 1,1,1,3,3,3-hexafluoro-2-propanol 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: Application
    Filed: November 15, 2013
    Publication date: June 12, 2014
    Applicant: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Jun Hatakeyama, Koji Hasegawa, Masaki Ohashi
  • Patent number: 8748076
    Abstract: There is disclosed a resist composition comprising at least: (A) a polymer containing one or more repeating units having a structure shown by the following general formula (1) and/or (2), an alkaline-solubility of the polymer being increased by an acid, (B) a photo acid generator generating, with responding to a high energy beam, a sulfonic acid shown by the following general formula (3), and (C) an onium sulfonate shown by the following general formula (4). There can be a resist composition showing not only excellent LWR and pattern profile but also extremely good performance in pattern-fall resistance, and to provide a patterning process using the same.
    Type: Grant
    Filed: January 6, 2012
    Date of Patent: June 10, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takayuki Nagasawa, Tomohiro Kobayashi, Ryosuke Taniguchi, Masaki Ohashi
  • Publication number: 20140154624
    Abstract: Disclosed herein is a photosensitive composition comprising a heterocyclic thiol compound or tautomeric form thereof and its method of use on a substrate, which may include a chalcophile substrate.
    Type: Application
    Filed: December 4, 2012
    Publication date: June 5, 2014
    Applicant: AZ ELECTRONIC MATERIALS (LUXEMBOURG) S.A.R.L.
    Inventors: Weihong LIU, Ping-Hung LU, Medhat TOUKHY, SookMee LAI, Yoshiharu SAKURAI, Aritaka HISHIDA
  • Patent number: 8741541
    Abstract: A compound represented by formula (I): wherein T1 represents a single bond or a C6-C14 aromatic hydrocarbon group, L1 represents a C1-C17 divalent saturated hydrocarbon group in which a methylene group may be replaced by an oxygen atom or a carbonyl group, L2 and L3 each independently represent a single bond or a C1-C6 divalent saturated hydrocarbon group in which a methylene group may be replaced by an oxygen atom or a carbonyl group, ring W1 and ring W2 each independently represent a C3-C36 hydrocarbon ring, R1 and R2 each independently represent a hydrogen atom, a hydroxyl group, or C1-C6 alkyl group, R3 and R4 each independently represent a hydroxyl group, or C1-C6 alkyl group, R5 represents a hydroxyl group or a methyl group, m represents 0 or 1, and t and u each independently represent an integer of 0 to 2.
    Type: Grant
    Filed: May 18, 2012
    Date of Patent: June 3, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Isao Yoshida
  • Patent number: 8741542
    Abstract: Provided is an actinic ray-sensitive or radiation-sensitive resin composition comprising (A) a specific compound represented by a general formula, (B) a resin which is alkali-insoluble or sparingly alkali-soluble and becomes easily alkali-soluble in the presence of an acid, and (C) a compound capable of generating an acid upon irradiation with an actinic ray or radiation; a film formed using the composition; and a pattern forming method using the same.
    Type: Grant
    Filed: November 30, 2010
    Date of Patent: June 3, 2014
    Assignee: FUJIFILM Corporation
    Inventors: Tomotaka Tsuchimura, Takayuki Ito, Toru Fujimori, Kana Fujii
  • Patent number: 8741554
    Abstract: A pattern is formed by coating a first positive resist composition comprising a base resin, a photoacid generator, and a base generator onto a substrate to form a first resist film, patternwise exposure, PEB, and development to form a first resist pattern, heating the first resist pattern for causing the base generator to generate a base for inactivating the pattern to acid, coating a second positive resist composition comprising a C3-C8 alcohol and an optional C6-C12 ether onto the first resist pattern-bearing substrate to form a second resist film, patternwise exposure, PEB, and development to form a second resist pattern.
    Type: Grant
    Filed: May 26, 2010
    Date of Patent: June 3, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Kazuhiro Katayama, Youichi Ohsawa, Masaki Ohashi
  • Patent number: 8741543
    Abstract: A resist composition having a resin having a structural unit represented by the formula (I), a resin being insoluble or poorly soluble in alkali aqueous solution, but becoming soluble in an alkali aqueous solution by the action of an acid and not including the structural unit represented by the formula (I), and an acid generator having an acid labile group, wherein R1, A1, A13, A14, X12 are defined in the specification.
    Type: Grant
    Filed: July 18, 2012
    Date of Patent: June 3, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Satoshi Yamaguchi, Yuki Suzuki
  • Patent number: 8741548
    Abstract: A pattern is formed by applying a first positive resist composition onto a substrate, heat treatment, exposure, heat treatment and development to form a first resist pattern; causing the first resist pattern to crosslink and cure by irradiation of high-energy radiation of up to 180 nm wavelength or EB; further applying a second positive resist composition onto the substrate, heat treatment, exposure, heat treatment and development to form a second resist pattern. The double patterning process reduces the pitch between patterns to one half.
    Type: Grant
    Filed: August 19, 2008
    Date of Patent: June 3, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Takao Yoshihara, Katsuya Takemura, Yoshio Kawai
  • Patent number: 8735046
    Abstract: A polymer obtained from copolymerization of a recurring unit having a carboxyl group and/or phenolic hydroxyl group substituted with an acid labile group with a methacrylate having a phenolic hydroxyl-bearing pyridine is useful as a base resin in a positive resist composition. The resist composition comprising the polymer is improved in contrast of alkali dissolution rate before and after exposure, acid diffusion control, resolution, and profile and edge roughness of a pattern after exposure.
    Type: Grant
    Filed: November 21, 2011
    Date of Patent: May 27, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Koji Hasegawa
  • Patent number: 8735052
    Abstract: A surface modifying material for forming a surface modifying layer provided between a substrate and a resist film, the surface modifying material including an epoxy resin having a weight average molecular weight of 1,000 to 50,000; a method of forming a resist pattern, including: forming a surface modifying layer on a substrate using the surface modifying material, forming a resist film on the substrate, on which the surface modified layer has been formed, using a resist composition, conducting exposure of the resist film, and alkali developing the resist film to form a resist pattern; and a method of forming a pattern, including: etching the substrate, on which a resist pattern has been formed by the method of forming a resist pattern.
    Type: Grant
    Filed: March 14, 2011
    Date of Patent: May 27, 2014
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Isao Hirano, Junichi Tsuchiya
  • Patent number: 8735049
    Abstract: A method of making a relief printing element in a liquid photopolymer platemaking process is described. The method comprises the steps of: (a) selectively exposing the liquid photopolymer to actinic radiation through a negative to crosslink and cure portions of the liquid photopolymer; and (b) reclaiming uncured portions of the liquid photopolymer to be reused in the platemaking process. The step of reclaiming uncured portions of the liquid photopolymer comprises (i) heating the printing element to decrease the viscosity of the uncured liquid photopolymer; and (ii) removing uncured liquid photopolymer from the surface of the relief image printing element so that recovery of uncured liquid photopolymer from the surface of the relief image printing element is enhanced.
    Type: Grant
    Filed: May 22, 2012
    Date of Patent: May 27, 2014
    Inventor: Ryan W. Vest
  • Patent number: 8735048
    Abstract: An actinic ray-sensitive or radiation-sensitive resin composition comprising (P) a resin having a repeating unit represented by the following formula (1), a resist film using the composition, and a pattern forming method.
    Type: Grant
    Filed: January 27, 2011
    Date of Patent: May 27, 2014
    Assignee: FUJIFILM Corporation
    Inventors: Takeshi Inasaki, Takayuki Ito, Tomotaka Tsuchimura, Tadateru Yatsuo, Koutarou Takahashi