Cationic Or Anionic Patents (Class 430/914)
  • Patent number: 9040224
    Abstract: A resist composition which generates acid upon exposure and exhibits changed solubility in a developing solution under action of acid, including a base component (A) which exhibits changed solubility in a developing solution under action of acid, and a photo-decomposable quencher (D0) containing a compound represented by general formula (d0) shown below. In the formula, R1 represents a hydrocarbon group of 4 to 20 carbon atoms which may have a substituent; Y1 represents a single bond or a divalent linking group; R2 and R3 each independently represents a substituent of 0 to 20 carbon atoms other than a fluorine atom; one of R2 and R3 may form a ring with Y1; Mm+ represents an organic cation having a valency of m; and m represents an integer of 1 or more.
    Type: Grant
    Filed: December 18, 2013
    Date of Patent: May 26, 2015
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Akiya Kawaue, Takaaki Kaiho, Tsuyoshi Nakamura
  • Patent number: 9034559
    Abstract: A pattern-forming method includes providing a resist film on a substrate using a radiation-sensitive composition. The resist film is exposed. The exposed resist film is developed using a developer solution. The developer solution includes no less than 80% by mass of an organic solvent. The radiation-sensitive composition includes at least two components including a first polymer and a radiation-sensitive acid generator. The first polymer includes a structural unit having an acid-labile group. One or more components of the radiation-sensitive composition have a group represented by a formula (1). A? represents —N?—SO2—RD, —COO?, —O? or —SO3?. —SO3? does not directly bond to a carbon atom having a fluorine atom. RD represents a linear or branched monovalent hydrocarbon group, or the like. X+ represents an onium cation.
    Type: Grant
    Filed: April 19, 2013
    Date of Patent: May 19, 2015
    Assignee: JSR CORPORATION
    Inventors: Hirokazu Sakakibara, Masafumi Hori, Taiichi Furukawa, Koji Ito
  • Patent number: 9017924
    Abstract: A resist composition which generates acid upon exposure and exhibits changed solubility in a developing solution under action of acid, including a base component (A) which exhibits changed solubility in a developing solution under action of acid, the base component (A) including a polymeric compound (A1) containing a structural unit (a0) represented by general formula (a0-1) shown below. In the formula, W1 represents a group which is formed by polymerization reaction of a group containing a polymerizable group; Y1 and Y2 each independently represents a divalent linking group; Y3 represents a carbonyl group or an alkylene group; R2 and R3 each independently represents a fluorine atom or a fluorinated alkyl group; Mm+ represents an organic cation having a valency of m; and m represents an integer of 1 or more.
    Type: Grant
    Filed: March 4, 2014
    Date of Patent: April 28, 2015
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Daichi Takaki, Yoshiyuki Utsumi
  • Patent number: 9017919
    Abstract: A resist composition containing a base component (A) which exhibits changed solubility in a 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) having a group represented by general formula (b1-1) shown below in the cation moiety.
    Type: Grant
    Filed: October 27, 2011
    Date of Patent: April 28, 2015
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Yoshiyuki Utsumi, Akiya Kawaue, Yoshitaka Komuro, Kenichiro Miyashita
  • Patent number: 9005874
    Abstract: There are provided a novel compound, a polymeric compound, a resist composition, an acid generator and a method of forming a resist pattern the compound represented by general formula (1-1): wherein each of R1 and R3 independently represents a single bond or a divalent linking group; A represents a divalent linking group; each of R2 and R4 independently represents a hydroxyl group, a hydrocarbon group which may have a substituent, or a group represented by general formula (1-an1), (1-an2) or (1-an3), provided that at least one of R2 and R4 represents a group represented by general formula (1-an1), (1-an2) or (1-an3); and n0 is preferably 0 or 1, and wherein Y1 represents a single bond or —SO2—; R5 represents a linear or branched monovalent hydrocarbon group of 1 to 10 carbon atoms, cyclic monovalent hydrocarbon group of 3 to 20 carbon atoms or monovalent hydrocarbon group of 3 to 20 carbon atoms having a cyclic partial structure which may be substituted with a fluorine atom; and M+ represents an organic ca
    Type: Grant
    Filed: April 18, 2012
    Date of Patent: April 14, 2015
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Yoshitaka Komuro, Yoshiyuki Utsumi, Akiya Kawaue, Masatoshi Arai
  • Patent number: 8980526
    Abstract: Disclosed are a hydrophilic photoacid generator prepared by copolymerization of a first (meth)acrylic acid ester having a structure represented by the following Formula 1 or 2, with a polymerizable monomer selected from the group consisting of a second (meth)acrylic acid ester, an olefin-based compound and a mixture thereof, each of which contains a functional group selected from the group consisting of a hydroxyl group, a carboxyl group, a lactone group, a nitrile group and a halogen group: wherein respective substituents are defined in the specification, and a resist composition comprising the same. The hydrophilic photoacid generator is uniformly dispersed in a resist film, thus improving a line edge roughness of resist patterns.
    Type: Grant
    Filed: December 13, 2012
    Date of Patent: March 17, 2015
    Assignee: Korea Kumho Petrochemical Co., Ltd.
    Inventors: Dae Kyung Yoon, Kyoung Jin Ryu, Sung Jae Lee, Hyun Sang Joo
  • Patent number: 8968458
    Abstract: A composition for a resist underlayer film is provided. The composition has excellent storage stability and can form a resist underlayer film which has excellent adhesion to a resist film, can improve reproducibility of a resist pattern and is resistant to an alkaline liquid used in development and to oxygen asking during the removal of a resist. The composition comprises a hydrolyzate and/or a condensate of a silane compound of the following formula (A), R1bR2cSi(OR3)4-a??(A) wherein R1 is a monovalent organic group having at least one unsaturated bond, R2 individually represents a hydrogen atom, a halogen atom or a monovalent organic group, R3 individually represents a monovalent organic group, R1 is a group other than OR3, a is an integer of 1 to 3, b is an integer of 1 to 3, and c is an integer of 0 to 2, provided that a=b+c.
    Type: Grant
    Filed: March 2, 2010
    Date of Patent: March 3, 2015
    Assignee: JSR Corporation
    Inventors: Keiji Konno, Masato Tanaka, Momoko Ishii, Junichi Takahashi, Tomoki Nagai
  • Patent number: 8956802
    Abstract: Provided is a negative type pattern forming method that satisfies high sensitivity, high resolution, good roughness and good dry etching resistance at the same time, and further, has a good development time dependency, the method including (i) forming a film by a chemical amplification resist composition containing (A) a fullerene derivative having an acid-decomposable group, (B) a compound generating an acid upon irradiation with an actinic ray or radiation, and (C) a solvent, (ii) exposing the film, and (iii) developing the exposed film by using an organic solvent-containing developer.
    Type: Grant
    Filed: March 15, 2013
    Date of Patent: February 17, 2015
    Assignee: FUJIFILM Corporation
    Inventor: Kaoru Iwato
  • Patent number: 8945814
    Abstract: Acid generator compounds are provided that are particularly useful as photoresist composition components. Preferred acid generators include cyclic sulfonium compounds that comprise a covalently linked acid-labile group.
    Type: Grant
    Filed: September 16, 2013
    Date of Patent: February 3, 2015
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: James F. Cameron, Vipul Jain, Paul J. LaBeaume, Jin Wuk Sung, James W. Thackeray
  • Patent number: 8940473
    Abstract: A resist composition contains (A1) a resin having a structural unit represented by the formula (I), (A2) 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 (B) an acid generator represented by the formula (II). wherein R1 represents a hydrogen atom or a methyl group; A1 represents a C1 to C6 alkanediyl group; R2 represents a C1 to C10 hydrocarbon group having a fluorine atom; R3 and R4 independently represent a fluorine atom or a C1 to C6 perfluoroalkyl group; X1 represents an C1 to C17 divalent saturated hydrocarbon group; R5 represents a group having cyclic ether structure; and Z1+ represents an organic cation.
    Type: Grant
    Filed: February 24, 2012
    Date of Patent: January 27, 2015
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Yuichi Mukai, Satoshi Yamamoto
  • Patent number: 8883396
    Abstract: A resist composition containing a base component (A) which generates an acid upon exposure and exhibits changed solubility in a developing solution by the action of acid, wherein the base component (A) contains a copolymer (A1) having a structural unit (a0) containing a group represented by the following general formula (a0-1) or (a0-2), a structural unit (a11) containing an acid-decomposable group which exhibits increased polarity by the action of acid and contains a polycyclic group, and a structural unit (a12) containing an acid-decomposable group which exhibits increased polarity by the action of acid and contains a monocyclic group. Each of the groups —R3—S+(R4)(R5) and Mm+ in the formula has only one aromatic ring as a whole or has no aromatic ring.
    Type: Grant
    Filed: October 31, 2012
    Date of Patent: November 11, 2014
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Masahito Yahagi, Jun Iwashita
  • Patent number: 8871427
    Abstract: There is disclosed a positive resist composition comprising (A) a resin having repeating units shown by the following general formulae (1) and (2) as repeating units that contain acid labile groups and being capable of increasing its alkaline solubility by an acid, (B) a photoacid generator, (C) a compound shown by the following general formula (3), and (D) a solvent. There can be a positive resist composition having high resolution, and at the same time giving an excellent pattern profile; and a patterning process in which an immersion lithography is carried out using a formed top coat.
    Type: Grant
    Filed: June 18, 2012
    Date of Patent: October 28, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Ryosuke Taniguchi, Akihiro Seki, Kenji Funatsu, Katsuhiro Kobayashi
  • Patent number: 8865392
    Abstract: Disclosed is a photosensitive resin composition containing a cationic photopolymerization initiator (A) and an epoxy resin (B) having two or more epoxy groups in each molecule, which is characterized in that the cationic photopolymerization initiator (A) is a cationic photopolymerization initiator (A-1) that is represented by formula (1).
    Type: Grant
    Filed: July 13, 2011
    Date of Patent: October 21, 2014
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Misato Oonishi, Naoko Imaizumi, Ryo Sakai, Nao Honda, Tadayuki Kiyoyanagi
  • Patent number: 8846290
    Abstract: An actinic ray-sensitive or radiation-sensitive resin composition includes: (A) a resin capable of increasing a solubility of the resin (A) in an alkali developer by an action of an acid; and (B) a compound capable of generating an acid upon irradiation with an actinic ray or radiation, wherein (B) the compound capable of generating an acid upon irradiation with an actinic ray or radiation is contained in an amount of 10 to 30 mass % based on the entire solid content of the actinic ray-sensitive or radiation-sensitive resin composition, and a pattern forming method uses the composition.
    Type: Grant
    Filed: March 26, 2010
    Date of Patent: September 30, 2014
    Assignee: FUJIFILM Corporation
    Inventors: Naohiro Tango, Michihiro Shirakawa, Mitsuhiro Fujita, Shuhei Yamaguchi, Akinori Shibuya, Shohei Kataoka
  • Patent number: 8841059
    Abstract: A negative resist composition, which shows excellent sensitivity and resolution in pattern formation by exposure to electron beams or EUV, a novel crosslinking agent suitable for the resist composition, and a pattern forming method using the resist composition are presented. The negative resist composition comprises: (A) a polyphenol compound comprising two or more phenolic hydroxyl groups in a molecule thereof and having a molecular weight of 300 to 3,000, (B) an acid generator which directly or indirectly produces acid by exposure to active energy rays having a wavelength of 248 nm or less, and (C) a crosslinking agent represented by the chemical formula (1).
    Type: Grant
    Filed: September 29, 2009
    Date of Patent: September 23, 2014
    Assignee: Dai Nippon Printing Co., Ltd.
    Inventors: Kenichi Okuyama, Yasunori Nagatsuka
  • Patent number: 8808446
    Abstract: A composition for a resist underlayer film is provided. The composition has excellent storage stability and can form a resist underlayer film which has excellent adhesion to a resist film, can improve reproducibility of a resist pattern and is resistant to an alkaline liquid used in development and to oxygen ashing during the removal of a resist. The composition comprises a hydrolyzate and/or a condensate of a silane compound of the following formula (A), R1bR2cSi(OR3)4-a??(A) wherein R1 is a monovalent organic group having at least one unsaturated bond, R2 individually represents a hydrogen atom, a halogen atom or a monovalent organic group, R3 individually represents a monovalent organic group, R1 is a group other than OR3, a is an integer of 1 to 3, b is an integer of 1 to 3, and c is an integer of 0 to 2, provided that a=b+c.
    Type: Grant
    Filed: February 24, 2006
    Date of Patent: August 19, 2014
    Assignee: JSR Corporation
    Inventors: Keiji Konno, Masato Tanaka, Momoko Ishii, Junichi Takahashi, Tomoki Nagai
  • Patent number: 8748074
    Abstract: Polymers and compositions for forming self-imageable films encompassing such polymers that encompass norbornene-type repeating unit having at least one phenolic functionality and maleic anhydride-type repeating unit, which can be formulated to be either positive tone imaging or negative tone imaging. The films formed thereby are useful as self-imageable layers in the manufacture of microelectronic, such as semiconductor, and optoelectronic devices.
    Type: Grant
    Filed: November 23, 2011
    Date of Patent: June 10, 2014
    Assignees: Promerus, LLC, Sumitomo Bakelite Co., Ltd.
    Inventors: Osamu Onishi, Haruo Ikeda, Larry F. Rhodes, Pramod Kandanarachchi
  • Patent number: 8703387
    Abstract: A resist composition comprising a base component (A) which exhibits changed solubility in a developing solution under action of acid and an acid-generator component (B) which generates acid upon exposure, the acid-generator component (B) comprising an acid generator (B1) composed of a compound represented by general formula (b1-1) shown below [wherein, X represents a cyclic group of 3 to 30 carbon atoms which may have a substituent, provided that a ring skelton of the cyclic group contains an —SO2— bond or an —O—SO2— bond, and at least one carbon atom which is not adjacent to the —SO2— bond or the —O—SO2— bond has an oxygen atom as a substituent; Q1 represents a divalent linking group or a single bond; Y1 represents an alkylene group which may have a substituent or a fluorinated alkylene group which may have a substituent; and A+ represents an organic cation].
    Type: Grant
    Filed: May 23, 2012
    Date of Patent: April 22, 2014
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Akiya Kawaue, Yoshiyuki Utsumi
  • Patent number: 8617786
    Abstract: The present invention relates to compositions comprising poly-oxycarbosilane and methods for using the compositions in step and flash imprint lithography. The imprinting compositions comprise a poly-oxycarbosilane polymer, a silanol, a reaction initiator and optionally a pore generator.
    Type: Grant
    Filed: February 11, 2011
    Date of Patent: December 31, 2013
    Assignee: International Business Machines Corporation
    Inventors: Richard Anthony Dipietro, Geraud Jean-Michel Dubois, Robert Dennis Miller, Ratnam Sooriyakumaran
  • Patent number: 8609321
    Abstract: A radiation-sensitive resin composition includes a polymer having a structural unit represented by a formula (I). In the formula (I), R1 represents a hydrogen atom or a methyl group. X represents a bivalent alicyclic hydrocarbon group not having or having a substituent. Y represents a bivalent hydrocarbon group having 1 to 20 carbon atoms. R2 represents a methyl group or a trifluoromethyl group.
    Type: Grant
    Filed: March 8, 2013
    Date of Patent: December 17, 2013
    Assignee: JSP Corporation
    Inventors: Hiromitsu Nakashima, Reiko Kimura, Kazuo Nakahara, Mitsuo Sato
  • Patent number: 8507172
    Abstract: A positive resist composition comprises: (A) a compound capable of generating an acid upon irradiation with actinic rays or radiation; (B) a resin of which solubility in an alkali developer increases under action of an acid; and (C) a compound capable of decomposing under action of an acid to generate an acid.
    Type: Grant
    Filed: January 28, 2008
    Date of Patent: August 13, 2013
    Assignee: FUJIFILM Corporation
    Inventor: Kenji Wada
  • Patent number: 8507180
    Abstract: Disclosed are a chemically amplified positive-type photoresist composition for a thick film, a chemically amplified dry film for a thick film, and a method for producing a thick film resist pattern, all of which are capable of obtaining a satisfactory resist pattern with high sensitivity even on a substrate having a portion formed of copper on an upper surface thereof. The chemically amplified positive-type photoresist composition for a thick film comprises component (A) which includes at least one compound capable of producing an acid upon irradiation with an actinic ray or radiation, and component (B) which includes at least one resin whose alkali solubility increases by the action of an acid, in which the component (A) includes an onium fluorinated alkyl fluorophosphate having a specific structure.
    Type: Grant
    Filed: October 18, 2007
    Date of Patent: August 13, 2013
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Yasushi Washio, Kazuhide Uno, Koichi Misumi, Takahiro Senzaki, Koji Saito, Nobuko Ohgake
  • Patent number: 8486605
    Abstract: A positive resist composition including: a base material component (A) which exhibits increased solubility in an alkali developing solution under the action of acid; and an acid generator component (B) which generates acid upon exposure; dissolved in an organic solvent (S), wherein the base material component (A) includes a resin component (A1) having 4 types of specific structural units, and the organic solvent (S) includes from 60 to 99% by weight of an alcohol-based organic solvent (S1) and from 1 to 40% by weight of at least one organic solvent (S2) selected from the group consisting of propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether and cyclohexanone.
    Type: Grant
    Filed: January 21, 2010
    Date of Patent: July 16, 2013
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Masaru Takeshita, Yasuhiro Yoshii, Jiro Yokoya, Hirokuni Saito, Tsuyoshi Nakamura
  • Patent number: 8445178
    Abstract: A composition for radical polymerization includes a photosensitive material, a photoinitiator, a solvent, and a material for adjusting a size of a pattern. A method of forming a pattern using the composition is also disclosed.
    Type: Grant
    Filed: June 5, 2009
    Date of Patent: May 21, 2013
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Jong-jin Park, Kwang-hee Lee, Xavier Bulliard, Yun-hyuk Choi, Kwang-sup Lee
  • Patent number: 8415081
    Abstract: The present invention discloses a photosensitive resin composition which comprises (A) a compound having a molecule with at least one thiirane ring and a total number of a thiirane ring and/or an epoxy ring of at least 2 in the molecule, and (B) a photo acid generator, said composition having a refractive index of at least 1.6, and a method of obtaining a high refractive index periodical structure which comprises subjecting the photosensitive resin composition to photolithography.
    Type: Grant
    Filed: June 17, 2004
    Date of Patent: April 9, 2013
    Assignees: Cornell Research Foundation, Inc., Hitachi Chemical Co., Ltd.
    Inventors: Christopher K. Ober, Yasuharu Murakami
  • Patent number: 8394570
    Abstract: A sulfonium salt has formula (1) wherein R1 is a monovalent hydrocarbon group except vinyl and isopropenyl, R2, R3, and R4 are alkyl, alkenyl, oxoalkyl, aryl, aralkyl or aryloxoalkyl or may bond together to form a ring with the sulfur atom, and n is 1 to 3. A chemically amplified resist composition comprising the sulfonium salt is capable of forming a fine feature pattern of good profile after development due to high resolution, improved focal latitude, and minimized line width variation and profile degradation upon prolonged PED.
    Type: Grant
    Filed: December 3, 2009
    Date of Patent: March 12, 2013
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Masaki Ohashi, Takeshi Kinsho, Satoshi Watanabe, Youichi Ohsawa
  • Patent number: 8389197
    Abstract: The present invention provides a positive resist composition and a resist pattern forming method that are capable of forming a resist pattern with a reduced level of roughness. The positive resist composition includes the compound represented by the general formula (I) below. The present invention also provides the resist pattern forming method using the positive resist composition above. [wherein, in formula (I), R11 and R12 each represents, independently, an alkyl group of 1 to 10 carbon atoms or an aromatic hydrocarbon group, and may include a hetero atom in the structure thereof; R21 to R24 each represents, independently, a hydrogen atom or an acid dissociable, dissolution inhibiting group, and two of the R21 to R24 represents a hydrogen atom and the others represents an acid dissociable, dissolution inhibiting group; X is a group represented by general formulas (Ia) or (Ib) below].
    Type: Grant
    Filed: June 30, 2006
    Date of Patent: March 5, 2013
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Takako Hirosaki, Daiju Shiono, Taku Hirayama, Hideo Hada
  • Patent number: 8383316
    Abstract: New routes involving multi-step reversible photo-chemical reactions using two-step techniques to provide non-linear resist for lithography are described in this disclosure. They may provide exposure quadratically dependant on the intensity of the light. Several specific examples, including but not limited to using nanocrystals, are also described. Combined with double patterning, these approaches may create sub-diffraction limit feature density.
    Type: Grant
    Filed: July 6, 2007
    Date of Patent: February 26, 2013
    Assignee: Pixelligent Technologies, LLC
    Inventors: Gregory D. Cooper, Zhiyun Chen, Z Serpil Gonen Williams, Larry F. Thompson
  • Patent number: 8377627
    Abstract: A compound shown by the following formula (1).
    Type: Grant
    Filed: July 30, 2008
    Date of Patent: February 19, 2013
    Assignee: JSR Corporation
    Inventors: Daisuke Shimizu, Ken Maruyama, Toshiyuki Kai, Tsutomu Shimokawa
  • Patent number: 8354217
    Abstract: A salt represented by the formula (I-AA): wherein Q1 and Q2 each independently represent a fluorine atom or a C1-C4 perfluoroalkyl group, X1 represents a single bond etc., Y1 represents a C1-C36 aliphatic hydrocarbon group etc., A1 and A2 independently each represents a C1-C20 aliphatic hydrocarbon group etc., Ar1 represents a (m4+1)-valent C6-C20 aromatic hydrocarbon group which can have one or more substituents, B1 represents a single bond etc., m1 and m2 independently each represents an integer of 0 to 2, m3 represents an integer of 1 to 3, with the proviso that m1 plus m2 plus m3 equals 3, and m4 represents an integer of 1 to 3, and a photoresist composition comprising the salt represented by the formula (I-AA) and a resin comprising a structural unit having an acid-labile group and 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: May 25, 2010
    Date of Patent: January 15, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Masako Sugihara, Tatsuro Masuyama
  • Patent number: 8349534
    Abstract: A positive resist composition including: a polymeric compound (A1) having a structural unit (a0) that contains a “cyclic group containing —SO2—” on the side chain terminal, and a structural unit (a1) derived from an acrylate ester containing an acid dissociable, dissolution inhibiting group; an acid generator component (B); and a fluorine-containing resin component having a structural unit (f1) represented by general formula (f1-0): wherein 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; Q0 represents a single bond or a divalent linking group having a fluorine atom; and RX0 represents an acid dissociable, dissolution inhibiting group-containing group which may contain a fluorine atom, with the provision that at least one fluorine atom is contained in formula (f1-0).
    Type: Grant
    Filed: March 4, 2010
    Date of Patent: January 8, 2013
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Tsuyoshi Kurosawa, Hiroaki Shimizu
  • Patent number: 8338074
    Abstract: It is intended to provide the following resin composition for stereolithography which is superior in storage stability and aging stability during operation, shows no increase in viscosity upon prolonged storage, has a high light-curing sensitivity and, therefore, makes it possible to produce, upon photo irradiation, an object by stereolithography, which is superior in dimensional accuracy, fabricating accuracy, water resistance, moisture resistance and mechanical properties at a high fabricating speed and a high productivity.
    Type: Grant
    Filed: June 24, 2004
    Date of Patent: December 25, 2012
    Assignees: CMET Inc., San-Apro Ltd.
    Inventors: Takashi Ito, Tsuneo Hagiwara, Hideki Kimura, Masashi Date, Jiro Yamamoto
  • Patent number: 8318403
    Abstract: A salt represented by the formula (I-CC): wherein Q1 and Q2 each independently represent a fluorine atom etc., X1 represents a single bond etc., Y1 represents a C1-C36 aliphatic hydrocarbon group etc., A1 and A2 independently each represents a C1-C20 aliphatic hydrocarbon group etc., Ar1 represents a (m4+1)-valent C6-C20 aromatic hydrocarbon group which can have one or more substituents, B1 represents a single bond etc., B2 represents a group capable of being eliminated by the action of an acid, m1 and m2 independently each represents an integer of 0 to 2, m3 represents an integer of 1 to 3, with the proviso that m1 plus m2 plus m3 equals 3, and m4 represents an integer of 1 to 3, and a photoresist composition comprising the salt represented by the formula (I-CC) and a resin comprising a structural unit having an acid-labile group and 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: May 25, 2010
    Date of Patent: November 27, 2012
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Masako Sugihara, Tatsuro Masuyama
  • Patent number: 8288078
    Abstract: A photosensitive resin composition is provided that is highly safe, provides a coating film having superior uniformity, can improve the curing density of the cured resin pattern, and is capable of forming a micro resist pattern having a large film thickness and a high aspect ratio with high sensitivity and high resolving ability. According to a photosensitive resin composition including, in addition to an onium fluorinated alkyl fluorophosphate based cation polymerization initiator having a specific structure, a specified solvent or a specified sensitizing agent as essential components, a coating film having superior uniformity, can improve the curing density of the cured resin pattern, and also is capable of forming a micro resist pattern having a large film thickness and a high aspect ratio with high sensitivity and high resolving ability.
    Type: Grant
    Filed: January 11, 2008
    Date of Patent: October 16, 2012
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Takahiro Senzaki, Koichi Misumi, Atsushi Yamanouchi, Koji Saito
  • Patent number: 8278030
    Abstract: An object of the present invention is to provide a sulfonium salt that has sufficient photosensitivity by active energy rays, such as visible light, ultraviolet rays, electron beams, and X-rays. The present invention is a sulfonium salt represented by formula (1). It is noted that R1 is a group represented by formula (2); R2 and R3 each represent an aryl group having 6 to 30 carbon atoms, a heterocyclic hydrocarbon group having 4 to 30 carbon atoms, an alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, or an alkynyl group having 2 to 30 carbon atoms; X? represents a monovalent polyatomic anion; R4 to R6 each represent an alkyl group, or the like; k represents an integer of 0 to 4; m represents an integer of 0 to 3; n represents an integer of 0 to 4; and A represents a group represented by —S—, —O—, —SO—, —SO2—, or —CO—.
    Type: Grant
    Filed: April 27, 2009
    Date of Patent: October 2, 2012
    Assignee: San-Apro Limited
    Inventors: Issei Suzuki, Hideki Kimura
  • Patent number: 8216766
    Abstract: A polymer having a rate of dissolution in an alkaline developer that increases under the action of acid is provided. The polymer is prepared by reacting a hydrogenated ROMP polymer with an O-alkylating agent in the presence of a base.
    Type: Grant
    Filed: March 25, 2009
    Date of Patent: July 10, 2012
    Assignees: Shin-Etsu Chemical Co., Ltd., Mitsui Chemicals, Inc.
    Inventors: Takeru Watanabe, Takeshi Kinsho, Tomohiro Kobayashi, Tadahiro Sunaga, Yuichi Okawa, Hirofumi Io
  • Patent number: 8216768
    Abstract: A photoacid generator, which shows very high sensitivity in the near ultraviolet range of about 300 to 400 nm, and also can remarkably increase a reaction rate of a photoreactive composition using the same, and a photoreactive composition which can initiate the reaction even by irradiation with near ultraviolet light within a short time and also can obtain a desired reaction product.
    Type: Grant
    Filed: October 30, 2008
    Date of Patent: July 10, 2012
    Assignee: Sumitomo Seika Chemicals Co., Ltd.
    Inventors: Katsumasa Yamamoto, Hirofumi Yamaguchi, Michio Suzuki
  • Patent number: 8211619
    Abstract: The present invention provides: a positive photosensitive composition that yields an insulation layer superior not only in high transparency, but also in heat resistance enduring a temperature during the production of a substrate, solvent resistance, and anti-aging property as a permanent resist; a positive permanent resist utilizing the positive photosensitive composition; and a method for producing the positive permanent resist. The present invention provides: a positive photosensitive composition containing (A) a curable silicone resin having a silanol group, which resin has a structure obtained by a reaction between one or more cyclic siloxane compounds represented by the following general formula (1): and one or more arylalkoxysilane compounds represented by the following general formula (2): (B) diazonaphthoquinones, and (C) a solvent; a positive permanent resist using the positive photosensitive composition; and a method for producing the positive permanent resist.
    Type: Grant
    Filed: November 12, 2008
    Date of Patent: July 3, 2012
    Assignee: Adeka Corporation
    Inventors: Hiroshi Morita, Hiromi Sato, Atsushi Kobayashi, Jinichi Omi, Seiichi Saito
  • Patent number: 8211615
    Abstract: The present invention provides a copolymer which can prevent problems associated with immersion lithography (including occurrence of a pattern defect such as water mark, and variation in sensitivity or abnormal patterning due to elution of an additive such as a radiation-sensitive acid-generator) and which provides surface characteristics suitable for immersion lithography, and a composition containing the copolymer.
    Type: Grant
    Filed: October 30, 2007
    Date of Patent: July 3, 2012
    Assignee: Maruzen Petrochemical Co., Ltd.
    Inventors: Takanori Yamagishi, Tomo Oikawa, Takayoshi Okada
  • Patent number: 8198016
    Abstract: The present invention provides a patterning process, in which a resistance with regard to an organic solvent used for a composition for formation of a reverse film is rendered to a positive pattern to the degree of necessity and yet solubility into an alkaline etching liquid is secured, thereby enabling to finally obtain a negative image by a positive-negative reversal by performing a wet etching using an alkaline etching liquid. A resist patterning process of the present invention using a positive-negative reversal comprises at least a step of forming a resist film by applying a positive resist composition; a step of obtaining a positive pattern by exposing and developing the resist film; a step of crosslinking the positive resist pattern thus obtained; a step of forming a reverse film; and a step of reversing the positive pattern to a negative pattern by dissolving into an alkaline wet-etching liquid for removal.
    Type: Grant
    Filed: May 4, 2009
    Date of Patent: June 12, 2012
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Tsutomu Ogihara, Mutsuo Nakashima, Kazuhiro Katayama
  • Patent number: 8192914
    Abstract: A resist composition for immersion exposure and a method of forming a resist pattern are provided which can satisfy both of excellent resistance to an immersion medium and lithography properties. The resist composition for immersion exposure includes a resin component (A) which exhibits changed alkali solubility under action of acid and an acid-generator component (B) which generates acid upon irradiation, the resin component (A) including a resin (A1) which contains a fluorine atom and a resin (A2) which has a structural unit (a?) derived from acrylic acid and contains no fluorine atom, and the amount of the resin (A1) contained in the resin component (A) being within the range from 0.1 to 50% by weight.
    Type: Grant
    Filed: December 8, 2006
    Date of Patent: June 5, 2012
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventor: Makiko Irie
  • Patent number: 8187790
    Abstract: Disclosed are a polymer for a chemically amplified resist represented as and a resist composition using the same. In the above Chemical formula 1, X represents vinyl ether derivatives or olefin derivatives, at least one of R1, R2, R3, and R4 is an alkyl group with 1 to 30 carbon atoms containing at least one functional group of a hydrogen atom, an ether group, an ester group, a carbonyl group, an acetal group, an epoxy group, a nitryl group (—CN), and an aldehyde group, l, m, n, o and p respectively represent repeating units, l represents a real number of 0.05 to 0.5, m and n respectively represent real numbers of 0.1 to 0.7, o and p respectively represent real numbers of 0 to 0.7, and a sum of l, m, n, o and p is 1.
    Type: Grant
    Filed: April 2, 2009
    Date of Patent: May 29, 2012
    Assignee: Korea Kumho Petrochemical Co., Ltd.
    Inventors: Hyunsang Joo, Jinho Kim, Yonghwa Hong, Changsoo Lee
  • Patent number: 8187787
    Abstract: Disclosed is a fluorine-containing unsaturated carboxylic acid represented by formula (1), wherein R1 represents a polymerizable double-bond containing group, R3 represents a fluorine atom or fluorine-containing alkyl group, and W represents a bivalent linking group. This compound can provide a fluorine-containing polymer compound that has a weight-average molecular weight of 1,000-1,000,000 and contains a repeating unit represented by formula (2), wherein R3 and W are defined as above, each of R4, R5 and R6 independently represents a hydrogen atom, fluorine atom or monovalent organic group, at least two of R4, R5 and R6 may be combined to form a ring. This polymer compound can provide a chemically amplified resist composition that is transparent to KrF or ArF excimer laser light and has a high resolution and is capable of forming a pattern having a rectangular section with no swelling.
    Type: Grant
    Filed: June 26, 2008
    Date of Patent: May 29, 2012
    Assignee: Central Glass Company, Limited
    Inventors: Yoshimi Isono, Jonathan Joachim Jodry, Satoru Narizuka, Kazuhiro Yamanaka
  • Patent number: 8173349
    Abstract: A polymer compound is provided which is excellent in heat resistance and insulating property, and a photosensitive resin composition is provided which includes the polymer compound, and may form a cured pattern or a cured film excellent in pattern forming property, resolution, heat resistance and insulating property. Also, a method for forming a cured pattern excellent in pattern forming property, resolution, heat resistance and insulating property using the photosensitive resin composition, and an electronic device having high reliance for a semiconductor device or for a display device are provided. The photosensitive resin composition includes a polymer compound obtained by reacting a monomer represented by Formula (1) and a monomer represented by Formula (2), and a photosensitizing agent.
    Type: Grant
    Filed: March 25, 2009
    Date of Patent: May 8, 2012
    Assignee: FUJIFILM Corporation
    Inventors: Masanori Hikita, Yasufumi Ooishi, Kenichiro Sato
  • Patent number: 8173351
    Abstract: A compound shown by the following formula (1) can be used as a material for a radiation-sensitive composition capable of forming a resist film which effectively responds to electron beams or the like, exhibits low roughness, and can form a high precision minute pattern in a stable manner.
    Type: Grant
    Filed: January 8, 2008
    Date of Patent: May 8, 2012
    Assignee: JSR Corporation
    Inventors: Daisuke Shimizu, Ken Maruyama, Toshiyuki Kai, Tsutomu Shimokawa
  • Patent number: 8163463
    Abstract: A photoresist composition including an oxetane-containing compound represented by Formula 1 or 2, an oxirane-containing compound represented by Formula 3 or 4, a photoinitiator, and a solvent, a method of forming a pattern using the photoresist composition, and an inkjet print head including a polymerization product of the photoresist composition. The photoresist composition provides a polymerization product which resists formation of cracks due to an inner stress, and has excellent heat tolerance, excellent chemical resistance, excellent adhesiveness, and excellent durability.
    Type: Grant
    Filed: February 29, 2008
    Date of Patent: April 24, 2012
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Jin-baek Kim, Byung-ha Park, Kyu-sik Kim, Young-ung Ha, Su-min Kim
  • Patent number: 8158338
    Abstract: Methods and compositions for enhancing the sensitivity of a resist composition are disclosed. In one aspect, compositions for use with a matrix material (e.g., a lithographically sensitive polymeric material) can be formulated with an acid generator and a sensitizer, where the sensitizer can be present in a relatively small amount. The sensitizer can include a compound with one or more silicon-silicon bonds, and can act to enhance the efficiency of acid generation when the resist is impinged by a selected lithographic radiation. The methods of the present invention can be especially useful in performing short wavelength (e.g., less than 200 nm) lithography, or for processes such as e-beam lithography, which traditionally suffer from low throughput.
    Type: Grant
    Filed: July 8, 2008
    Date of Patent: April 17, 2012
    Assignee: Massachusetts Institute of Technology
    Inventor: Theodore H. Fedynyshyn
  • Patent number: 8148043
    Abstract: Silsesquioxane-based compositions that contain (a) silsesquioxane resins that contain HSiO3/2 units and RSiO3/2 units wherein; R is an acid dissociable group, and (b) least one organic base additive selected from bulky tertiary amines, imides, amides and the polymeric amines wherein the organic base additive contains an electron-attracting group with the provision that the organic base additive is not 7-diethylamino-4-methylcoumarin. The silsesquioxane-based compositions are useful as positive resist compositions in forming patterned features on substrate, particularly useful for multi-layer layer (i.e. bilayer) 193 nm & 157 nm photolithographic applications.
    Type: Grant
    Filed: June 27, 2007
    Date of Patent: April 3, 2012
    Assignee: Dow Corning Corporation
    Inventors: Sanlin Hu, Eric Scott Moyer
  • Patent number: 8124310
    Abstract: A positive resist composition includes: (A) a resin containing a repeating unit represented by formula (I) or (I?) as defined in the specification, of which solubility in an alkali developer increases under an action of an acid; and (B) a compound capable of generating an acid upon irradiation with actinic rays or radiation: and a pattern forming method uses the positive resist composition.
    Type: Grant
    Filed: September 26, 2008
    Date of Patent: February 28, 2012
    Assignee: Fujifilm Corporation
    Inventors: Shuji Hirano, Shinichi Sugiyama
  • Patent number: 8114571
    Abstract: Photoacid generators generate sulfonic acids of formula (1a) or (1b) upon exposure to high-energy radiation. R1—COOCH2CF2SO3?H+??(1a) R1—O—COOCH2CF2SO3?H+??(1b) R1 is a monovalent C20-C50 hydrocarbon group of steroid structure which may contain a heteroatom. The bulky steroid structure ensures adequate control of acid diffusion. The photoacid generators are compatible with resins and suited for use in chemically amplified resist compositions.
    Type: Grant
    Filed: April 30, 2009
    Date of Patent: February 14, 2012
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Masaki Ohashi, Youichi Ohsawa, Takeshi Kinsho, Takeru Watanabe