Polymer Of Unsaturated Acid Or Ester Patents (Class 430/910)
  • Patent number: 8440384
    Abstract: A compound has a partial structure shown by a following formula (1), wherein R1 represents a hydrogen atom or a substituted or unsubstituted hydrocarbon group having 1 to 8 carbon atoms, R2 represents a substituted or unsubstituted hydrocarbon group having 1 to 8 carbon atoms, Rf represents a fluorine atom or a perfluoroalkyl group having 1 to 4 carbon atoms, L represents an integer from 0 to 4, n represents an integer from 0 to 10, and m represents an integer from 1 to 4.
    Type: Grant
    Filed: April 14, 2010
    Date of Patent: May 14, 2013
    Assignee: JSR Corporation
    Inventors: Takuma Ebata, Tomoki Nagai
  • Patent number: 8435717
    Abstract: A sulfonic acid onium salt represented by the following formula (1) can be used as a superior radiosensitive acid generator for resist compositions. It is possible to form a good pattern by using a resist composition containing this sulfonic acid onium salt. In formula (1), R1 represents a monovalent organic group, and Q+ represents a sulfonium cation or iodonium cation.
    Type: Grant
    Filed: February 14, 2008
    Date of Patent: May 7, 2013
    Assignee: Central Glass Company, Limited
    Inventors: Yuji Hagiwara, Jonathan Joachim Jodry, Satoru Narizuka, Kazuhiko Maeda
  • Patent number: 8431326
    Abstract: The present invention provides a salt represented by the formula (I): wherein Q1 and Q2 independently each represent a fluorine atom or a C1-C6 perfluoroalkyl group, L1 represents a C1-C17 divalent saturated hydrocarbon group in which one or more —CH2— can be replaced by —O— or —CO—, ring W represents a C3-C36 aliphatic ring in which one or more —CH2— can be replaced by —O—, —S—, —CO— or —SO2— and in which one or more hydrogen atoms can be replaced by a hydroxyl group, a C1-C12 alkyl group, a C1-C12 alkoxy group, a C3-C12 alicyclic hydrocarbon group or a C6-C10 aromatic hydrocarbon group, Rf is independently in each occurrence a fluorine atom or a C1-C6 fluorinated alkyl group, n represents an integer of 1 to 10, and Z+ represents an organic counter ion.
    Type: Grant
    Filed: October 3, 2011
    Date of Patent: April 30, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Mitsuyoshi Ochiai, Takashi Hiraoka
  • Patent number: 8426110
    Abstract: A chemically amplified positive resist composition comprises an acid-decomposable keto ester compound of steroid skeleton which is insoluble in alkaline developer, but turns soluble in alkaline developer under the action of acid. The composition is exposed to EB, deep-UV or EUV and developed to form a pattern with a high resolution and improved LER.
    Type: Grant
    Filed: January 31, 2012
    Date of Patent: April 23, 2013
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takeru Watanabe, Tomohiro Kobayashi, Katsuya Takemura, Jun Hatakeyama
  • Patent number: 8426106
    Abstract: A Photoresist composition comprising a polymer comprising a structural unit derived from a compound represented by the formula (I): wherein R1 represents a hydrogen atom or a methyl group, R2 represents a C6-C12 aromatic hydrocarbon group which can have one or more substituents, R3 represents a cyano group or a C1-C12 hydrocarbon group which can have one or more substituents and which can contain one or more heteroatoms, A1 represents a single bond, —(CH2)g—CO—O—* or —(CH2)h—O—CO—(CH2)i—CO—O—* wherein g, h and i each independently represent an integer of ?1 to 6 and * represents a binding position to the nitrogen atom, a resin 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, and an acid generator.
    Type: Grant
    Filed: October 12, 2010
    Date of Patent: April 23, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tatsuro Masuyama, Kazuhiko Hashimoto, Junji Shigematsu
  • Patent number: 8420290
    Abstract: An acetal compound of formula (1) is provided wherein R1 is H, methyl or trifluoromethyl, R2 is a monovalent C1-C10 hydrocarbon group, R3 and R4 are H or a monovalent C1-C10 hydrocarbon group, R2 and R3 may together form an aliphatic hydrocarbon ring, and X1 is a single bond or a divalent C1-C4 hydrocarbon group. A polymer comprising recurring units derived from the acetal compound is used as a base resin to formulate a resist composition which exhibits a high resolution when processed by micropatterning technology, especially ArF lithography.
    Type: Grant
    Filed: November 25, 2009
    Date of Patent: April 16, 2013
    Assignee: Shin-Etsu Chemical Co., Ltd
    Inventors: Koji Hasegawa, Masaki Ohashi, Takeshi Kinsho, Tsunehiro Nishi, Masayoshi Sagehashi
  • Patent number: 8420292
    Abstract: A polymer comprising recurring units of formula (1) and having a solubility in alkaline developer which increases under the action of an alkaline developer is provided. The polymer has transparency to radiation of up to 200 nm and improved water repellency, water slip, acid lability and hydrolysis and is useful as an additive polymer to formulate a resist composition. R1 is H, F, methyl, or trifluoromethyl, R2 is a monovalent fluorinated hydrocarbon group, An is a (n+1)-valent hydrocarbon or fluorinated hydrocarbon group, and n is 1, 2 or 3.
    Type: Grant
    Filed: January 14, 2011
    Date of Patent: April 16, 2013
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Yuji Harada, Takeru Watanabe, Takeshi Sasami, Yuuki Suka, Koji Hasegawa
  • Patent number: 8420294
    Abstract: The present invention provides a salt represented by the formula (I): wherein R1 and R2 independently each represent a C1-C6 alkyl group or R1 and R2 are bonded each other to form a C5-C20 aliphatic ring together with the carbon atom to which they are bonded, R3 and R4 independently each represent a fluorine atom or a C1-C6 perfluoroalkyl group, X1 represents a C1-C17 divalent saturated hydrocarbon group in which one or more —CH2— can be replaced by —O— or —CO— and which may be substituted with one or more fluorine atoms, and Z1+ represents an organic counter ion.
    Type: Grant
    Filed: November 25, 2011
    Date of Patent: April 16, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Yukako Anryu, Shingo Fujita
  • Patent number: 8415085
    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: May 23, 2012
    Date of Patent: April 9, 2013
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hideo Hada, Yoshiyuki Utsumi, Takehiro Seshimo, Akiya Kawaue
  • Patent number: 8415083
    Abstract: This invention provides methods of creating via or trench structures on a developer-soluble hardmask layer using a multiple exposure-development process. The hardmask layer is patterned while the imaging layer is developed. After the imaging layer is stripped using organic solvents, the same hardmask can be further patterned using subsequent exposure-development processes. Eventually, the pattern can be transferred to the substrate using an etching process.
    Type: Grant
    Filed: May 24, 2011
    Date of Patent: April 9, 2013
    Assignee: Brewer Science Inc.
    Inventors: Sam X. Sun, Hao Xu, Tony D. Flaim
  • Patent number: 8404428
    Abstract: A fluorine-containing polymeric compound which contains a structural unit (f1) that is decomposable in an alkali developing solution as a block copolymer portion, a base component (A) that exhibits increased solubility in an alkali developing solution under the action of acid, and an acid generator component (B) that generates acid upon exposure.
    Type: Grant
    Filed: June 25, 2010
    Date of Patent: March 26, 2013
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Tasuku Matsumiya, Daiju Shiono, Tomoyuki Hirano, Takahiro Dazai
  • Patent number: 8404426
    Abstract: A negative resist composition including an alkali-soluble resin component (A), an acid generator component (B) that generates acid upon exposure, and a cross-linking component (C), the alkali-soluble resin component (A) including a polymeric compound (F) having a structural unit (f1) containing a base dissociable group and a structural unit (f2) containing a cross-linking group-containing group.
    Type: Grant
    Filed: July 6, 2009
    Date of Patent: March 26, 2013
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Sho Abe, Daiju Shiono, Tomoyuki Hirano, Takahiro Dazai
  • Patent number: 8399176
    Abstract: Disclosed is a photosensitive resin composition suitable for use in a transflective liquid crystal display (LCD). The photosensitive resin composition uses, as an alkali-soluble binder resin, a blend of two kinds of binder resins. The first binder resin has a weight average molecular weight greater than or equal to 1,000 but lower than 20,000 and contains no reactive group. The second binder resin has a weight average molecular weight greater than or equal to 20,000 but lower than 80,000 and contains reactive groups. The photosensitive resin composition has good adhesion to an underlying substrate while forming a high resolution fine pattern.
    Type: Grant
    Filed: February 26, 2010
    Date of Patent: March 19, 2013
    Assignee: LG Chem, Ltd.
    Inventors: Han Kook Kim, Sung Hyun Kim, Jae Joon Kim, Bog Ki Hong, Mi Ae Kim, Seung Jin Yang, Sang Moon Yoo, Sun Hwa Kim, Won Jin Chung
  • Patent number: 8394569
    Abstract: A resist composition for immersion lithography of the present invention includes a resin component (A) which exhibits changed alkali solubility under the action of acid; and an acid generator component (B) which generates acid on exposure, wherein the resin component (A) includes a resin (A1) containing a fluorine atom and no acid-dissociable group, and a resin (A2) containing a structural unit (a?) derived from an acrylic acid and no fluorine atom.
    Type: Grant
    Filed: February 5, 2007
    Date of Patent: March 12, 2013
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Makiko Irie, Takeshi Iwai
  • Patent number: 8372577
    Abstract: It is disclosed a photosensitive resin composition comprising (a) a binder polymer based on a copolymer containing benzyl (meth)acrylate as a building block, (b) a photopolymerizable compound having at least one polymerizable ethylenically unsaturated group in the molecule and (c) a photopolymerization initiator based on a hexarylbisimidazole compound, with a light-initiated color former being optionally contained as component (d). The composition has long-term keeping quality, exhibits particularly high resistance to plating and dry etching, as well as assuring improvement in resolution and adhesion; the composition may be used to form a photosensitive dry film.
    Type: Grant
    Filed: June 9, 2010
    Date of Patent: February 12, 2013
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Yukihiko Tanaka, Shinkichi Asahi, Naoya Katsumata
  • Patent number: 8367297
    Abstract: A resist composition including a base component (A) which exhibits changed solubility in an alkali developing solution under action of acid and an acid-generator component (B) which generates acid upon exposure, the acid-generator component (B) including an acid generator (B1) containing a compound having a cation moiety represented by general formula (I) (in the formula, R5 represents a hydrogen atom or an organic group of 1 to 30 carbon atoms which may have a substituent; and Q5 represents a single bond or a divalent linking group).
    Type: Grant
    Filed: December 9, 2009
    Date of Patent: February 5, 2013
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Akiya Kawaue, Yoshiyuki Utsumi, Shinichi Hidesaka, Natsuko Maruyama
  • Patent number: 8367296
    Abstract: A positive resist composition including a base component (A) which exhibits increased solubility in an alkali developing solution under action of acid and an acid-generator component (B) which generates acid upon exposure, the base component (A) including a polymeric compound (A1?) containing an acid dissociable, dissolution inhibiting group within the structure thereof and including a structural unit (a0) represented by general formula (a0-1) (R2 represents a divalent linking group, and A? represents an oxygen atom, a sulfur atom, or an alkylene group of 1 to 5 carbon atoms which may contain an oxygen atom or a sulfur atom) and a structural unit (a2) derived from an acrylate ester containing a lactone-containing cyclic group; or a polymeric compound (A1) including the structural unit (a0) and a structural unit (a1) derived from an acrylate ester containing an acid dissociable, dissolution inhibiting group.
    Type: Grant
    Filed: September 28, 2009
    Date of Patent: February 5, 2013
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Tomoyuki Hirano, Takahiro Dazai, Daiju Shiono, Tasuku Matsumiya
  • Patent number: 8367295
    Abstract: Provided are a preparation method of a resist composition which enables stabilization of a dissolution performance of a resist film obtained from the resist composition thus prepared; and a resist composition obtained by the preparation process and showing small lot-to-lot variations in degradation over time. The process of the present invention is for preparing a chemically amplified resist composition containing a binder, an acid generator, a nitrogenous basic substance and a solvent and it has steps of selecting, as the solvent, a solvent having a peroxide content not greater than an acceptable level, and mixing constituent materials of the resist composition in the selected solvent.
    Type: Grant
    Filed: April 28, 2008
    Date of Patent: February 5, 2013
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Keiichi Masunaga, Takanobu Takeda, Tamotsu Watanabe, Satoshi Watanabe, Ryuji Koitabashi, Osamu Watanabe
  • Patent number: 8361697
    Abstract: [Purpose] To provide a photosensitive resin composition having satisfactory compatibility during dry film formation, exhibiting similar sensitivity for exposure with both i-line radiation and h-line radiation type exposure devices, having excellent resolution and adhesiveness, allowing development with aqueous alkali solutions, and preferably, having no generation of aggregates during development. [Solution Means] A photosensitive resin composition comprising (a) 20-90 wt % of a thermoplastic copolymer having a specific copolymerizing component copolymerized, and having a carboxyl group content of 100-600 acid equivalents and a weight-average molecular weight of 5,000-500,000, (b) 5-75 wt % of an addition polymerizable monomer having at least one terminal ethylenic unsaturated group, (c) 0.01-30 wt % of a photopolymerization initiator containing a triarylimidazolyl dimer, and (d) 0.001-10 wt % of a pyrazoline compound.
    Type: Grant
    Filed: March 19, 2009
    Date of Patent: January 29, 2013
    Assignee: Asahi Kasei E-Materials Corporation
    Inventor: Yosuke Hata
  • Patent number: 8361703
    Abstract: A protective coating composition comprising a polymer of acyl-protected hexafluoroalcohol structure as a base polymer, optionally in admixture with a second polymer containing sulfonic acid amine salt in recurring units is applied onto a resist film. The protective coating is transparent to radiation of wavelength up to 200 nm.
    Type: Grant
    Filed: December 1, 2009
    Date of Patent: January 29, 2013
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Yuji Harada, Jun Hatakeyama, Koji Hasegawa
  • Patent number: 8357483
    Abstract: The present invention relates to a photosensitive resin composition that includes a polymer prepared by using a macromonomer as an alkali soluble resin. The photosensitive resin composition is used for various types of purposes such as a photoresist for preparing a color filter, an overcoat photoresist, a column spacer, and an insulating material having a light blocking property, and improves physical properties such as residue or not, chemical resistance, and heat resistance of the photoresist.
    Type: Grant
    Filed: April 11, 2008
    Date of Patent: January 22, 2013
    Assignee: LG Chem, Ltd.
    Inventors: Han-Soo Kim, Min-Young Lim, Yoon-Hee Heo, Ji-Heum Yoo, Sung-Hyun Kim, Kwang-Han Park
  • Patent number: 8349535
    Abstract: According to one embodiment, an actinic ray-sensitive or radiation-sensitive resin composition includes (A) a resin containing the repeating units of formulae (I), (II) and (III) that when acted on by an acid, becomes soluble in an alkali developer, and (B) a compound that when irradiated with actinic rays or radiation, generates a fluorine-containing acid, wherein each of R1 independently represents a hydrogen atom or an optionally substituted methyl group, R2 represents a halogen atom, an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted aryl group or an optionally substituted aralkyl group, and n is an integer of 0 to 5, provided that when n is 2 or greater, multiple R2s may be identical to or different from each other.
    Type: Grant
    Filed: September 30, 2010
    Date of Patent: January 8, 2013
    Assignee: FUJIFILM Corporation
    Inventors: Kana Fujii, Takamitsu Tomiga, Toru Tsuchihashi, Kazuyoshi Mizutani, Jiro Yokoyama, Shinichi Sugiyama, Shuji Hirano, Toru Fujimori
  • 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: 8343708
    Abstract: A positive photosensitive composition includes: (A) a resin that has an acid decomposable repeating unit of formula (I) and increases its solubility in an alkali developer by action of an acid; (B) a compound that generates an acid upon irradiation; (C) a resin that has: a fluorine atom and/or a silicon atom; and a group selected from groups (x) to (z); and (D) a solvent: (x) an alkali soluble group, (y) a group which decomposes by action of an alkali developer and increases a solubility of the resin (C) in an alkali developer, and (z) a group which decomposes by action of an acid, wherein, Xa1 represents hydrogen, alkyl, cyano or halogen, Ry1 to Ry3 each independently represents alkyl or cycloalkyl, and at least two of Ry1 to Ry3 may be coupled to form a ring, and Z represents a divalent linking group.
    Type: Grant
    Filed: September 9, 2011
    Date of Patent: January 1, 2013
    Assignee: FUJIFILM Corporation
    Inventors: Toshiaki Fukuhara, Hiromi Kanda, Shinichi Kanna
  • Patent number: 8338075
    Abstract: A positive resist composition including: a base 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), the organic solvent (S) including an alcohol-based organic solvent having a boiling point of at least 150° C.; and a method of forming a resist pattern including: applying the positive resist composition on a substrate on which a first resist pattern is formed to form a second resist film; and subjecting the second resist film to selective exposure and alkali developing to form a resist pattern.
    Type: Grant
    Filed: August 3, 2009
    Date of Patent: December 25, 2012
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Masaru Takeshita, Shinji Kumada, Yasuhiro Yoshii, Takeshi Iwai, Tsuyoshi Nakamura
  • Patent number: 8329377
    Abstract: An imide compound represented by the formula (I): wherein R1 represents a C1-C20 aliphatic hydrocarbon group etc., W1 represents —CO—O— etc., Q1 and Q2 each independently represent a fluorine atom etc., and A represents a group represented by the formula (I-1): wherein A1 represents —CH2—CH2— etc., and a chemically amplified resist composition containing the same.
    Type: Grant
    Filed: July 21, 2009
    Date of Patent: December 11, 2012
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Ichiki Takemoto, Tatsuro Masuyama, Takashi Hiraoka
  • Patent number: 8329378
    Abstract: A positive resist composition including a base 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, the base component (A) including a polymeric compound (A1) containing a structural unit (a0) having an aromatic group, a structural unit (a5) represented by general formula (a5-1) shown below, and a structural unit (a1) containing an acid-dissociable, dissolution-inhibiting group. In the formula (a5-1), R1 represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms, R2 represents a divalent linking group, and R3 represents a cyclic group containing —SO2— within the ring skeleton thereof.
    Type: Grant
    Filed: March 10, 2010
    Date of Patent: December 11, 2012
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Tomoyuki Hirano, Tasuku Matsumiya, Daiju Shiono, Takahiro Dazai
  • Patent number: 8318404
    Abstract: A salt represented by the formula (a1): wherein Q1 and Q2 each independently represent a fluorine atom or a C1-C4 perfluoroalkyl group, X1 represents —CO—O—Xa1— or —CH2—O—Xa2— wherein Xa1 and Xa2 independently each represent a C1-C15 alkylene group and one or more —CH2— in the alkylene group can be replaced by —O— or —CO—, Y1 represents a C3-C36 alicyclic hydrocarbon group or a C6-C24 aromatic hydrocarbon group, and the alicyclic hydrocarbon group and the aromatic hydrocarbon group can have one or more substituents, and one or more —CH2— in the alicyclic hydrocarbon group can be replaced by —O— or —CO—, and Z+ represents an organic cation.
    Type: Grant
    Filed: June 9, 2010
    Date of Patent: November 27, 2012
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Masako Sugihara, Hiromu Sakamoto
  • Patent number: 8304164
    Abstract: The present invention provides a photoresist composition comprising: at least one selected from the group consisting of a monomer represented by the formula (I): wherein R1 represents a hydrogen atom or a methyl group, W1 represents a C3-C20 divalent saturated cyclic hydrocarbon group, A1 represents a single bond or *-O—CO—W1— wherein * represents a binding position to W1?N— and W1 represents a C1-C10 divalent saturated hydrocarbon group, a polymer consisting of a structural unit derived from the monomer represented by the formula (I) and a polymer consisting of a structural unit derived from the monomer represented by the formula (I) and a structural unit derived from a monomer represented by the formula (II): wherein R3 represents a hydrogen atom or a methyl group, A2 represents a single bond or *-O—CO—(CH2)n— wherein * represents a binding position to R4—, n represents an integer of 1 to 7 and R4 represents a C3-C20 saturated cyclic hydrocarbon group, a resin having an acid-labile group
    Type: Grant
    Filed: January 3, 2011
    Date of Patent: November 6, 2012
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tatsuro Masuyama, Yuichi Mukai, Masahiko Shimada
  • Patent number: 8304169
    Abstract: The present invention relates to a novel alkali-developable resin, a method of producing the alkali-developable resin, a photosensitive resin composition including the alkali-developable resin, and a device that is manufactured by using the photosensitive composition. In the case of when the alkali-developable resin is used as a component of the photosensitive composition, the photosensitivity, the developability and the film remaining rate of the pattern are improved.
    Type: Grant
    Filed: February 11, 2008
    Date of Patent: November 6, 2012
    Assignee: LG Chem, Ltd.
    Inventors: Min-Young Lim, Han-Soo Kim, Yoon-Hee Heo, Ji-Heum Yoo, Sung-Hyun Kim
  • Patent number: 8298745
    Abstract: A polymeric compound including a structural unit (a0) represented by the structural unit (a0-1) shown below: (in the formula (a0-1), R1 represents a hydrogen atom, a lower alkyl group, or a halogenated lower alkyl group; R5 represents an alkyl group; R6 represents a substituent selected from the group consisting of an alkyl group, an alkoxy group, a halogen atom and a halogenated alkyl group; and e represents an integer of 0 to 5).
    Type: Grant
    Filed: June 11, 2008
    Date of Patent: October 30, 2012
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Sanae Furuya, Takahiro Dazai, Shinichi Kohno
  • Patent number: 8298746
    Abstract: The present invention provides a chemically amplified resist composition comprising: a resin (A) which itself is insoluble or poorly soluble in an aqueous alkali solution but becomes soluble in an aqueous alkali solution by the action of an acid and which comprises a structural unit having an acid-labile group in a side chain and a structural unit represented by the formula (I): wherein R1 represents a hydrogen atom or a methyl group, ring X1 represents an unsubstituted or substituted C3-C30 cyclic hydrocarbon group having —COO— and k represents an integer of 1 to 4, a resin (B) which comprises a structural unit represented by the formula (II): wherein R2 represents a hydrogen atom, a methyl group or a trifluoromethyl group, and an acid generator.
    Type: Grant
    Filed: June 24, 2009
    Date of Patent: October 30, 2012
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Junji Shigematsu, Kunishige Edamatsu, Takayuki Miyagawa, Akira Kamabuchi
  • Patent number: 8298748
    Abstract: A positive resist composition including a base component (A?) which exhibits increased solubility in an alkali developing solution under action of acid and generates acid upon exposure, the base component (A?) including a polymeric compound (A1?) having a structural unit (a5-1) represented by general formula (a5-1), a structural unit (a0-1) represented by general formula (a0-1) and a structural unit (a0-2) that generates acid upon exposure, the structural unit (a0-2) containing a group represented by general formula (a0-2?) (wherein X? represents an anion moiety represented by one of general formulas (1) to (5)).
    Type: Grant
    Filed: May 17, 2010
    Date of Patent: October 30, 2012
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Takehiro Seshimo, Yoshiyuki Utsumi, Yoshitaka Komuro, Takeyoshi Mimura, Daichi Takaki
  • Patent number: 8288077
    Abstract: The object of the present invention is to provide a chemically amplified resist composition excellent in a resolution and a mask error enhancement factor. By employing the salt represented by the formulae (A1) as an acid generator of a resist composition, the above mentioned object is achieved. wherein Z+ represents an organic cation, Q1 and Q2 each independently represent a fluorine atom or a perfluoroalkyl group, Ra2 represents a divalent alicyclic hydrocarbon group pr the like, Ra2 represents an elimination group represented by the formulae (II-1) or (II-2). In the formulae (II-1) or (II-2), Ra3 and Ra4 each independently represent a hydrogen atom or an aliphatic hydrocarbon group, Ra5 represents an aliphatic hydrocarbon group, Ra6 represents a divalent aliphatic hydrocarbon group, and Ra7 represents an aliphatic hydrocarbon group.
    Type: Grant
    Filed: July 27, 2010
    Date of Patent: October 16, 2012
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Isao Yoshida, Satoshi Yamaguchi
  • Patent number: 8288076
    Abstract: A chemically amplified resist composition comprises a polymer comprising units having polarity to impart adhesion and acid labile units adapted to turn alkali soluble under the action of acid. The polymer comprises recurring units having formula (1) wherein R1 is H, F, CH3 or CF3, Rf is H, F, CF3 or CF2CF3, A is a divalent hydrocarbon group, R2, R3 and R4 are alkyl, alkenyl, oxoalkyl, aryl, aralkyl or aryloxoalkyl. Recurring units containing an aromatic ring structure are present in an amount ?60 mol % and the recurring units having formula (1) are present in an amount <5 mol %.
    Type: Grant
    Filed: May 28, 2010
    Date of Patent: October 16, 2012
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Keiichi Masunaga, Satoshi Watanabe, Akinobu Tanaka, Daisuke Domon
  • Patent number: 8283106
    Abstract: Disclosed is a fluorinated sulfonic acid salt or fluorinated sulfonic acid group-containing compound having a structure represented by the following general formula (A). In the formula, n indicates an integer of 1 to 10; R indicates a substituted or unsubstituted C1-C20 linear, branched or cyclic alkyl group, a substituted or unsubstituted C1-C20 linear, branched or cyclic alkenyl group, a substituted or unsubstituted C6-C15 aryl group, or a C4-C15 heteroaryl group; and a indicates 1 or 0. A photoacid generator containing the above fluorinated sulfonic acid salt or fluorinated sulfonic acid group-containing compound shows high sensitivity to an ArF excimer laser or the like, presents no concerns about human body accumulation, can generate an acid (photoacid) of sufficiently high acidity, and exhibits high solubility in a resist solvent and good compatibility with a resist resin.
    Type: Grant
    Filed: October 31, 2008
    Date of Patent: October 9, 2012
    Assignee: Central Glass Company, Limited
    Inventors: Kazuhiko Maeda, Yoshimi Isono, Satoru Narizuka
  • Patent number: 8283104
    Abstract: There is disclosed a sulfonate shown by the following general formula (2). R1—COOC(CF3)2—CH2SO3?M+??(2) (In the formula, R1 represents a linear, a branched, or a cyclic monovalent hydrocarbon group having 1 to 50 carbon atoms optionally containing a hetero atom. M+ represents a cation.) There can be provided: a novel sulfonate which is effective for a chemically amplified resist composition having a sufficiently high solubility (compatibility) in a resist solvent and a resin, a good storage stability, a PED stability, a further wider depth of focus, a good sensitivity, in particular a high resolution and a good pattern profile form; a photosensitive acid generator; a resist composition using this; a photomask blank, and a patterning process.
    Type: Grant
    Filed: February 16, 2010
    Date of Patent: October 9, 2012
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Masaki Ohashi, Takeshi Kinsho, Youichi Ohsawa
  • Patent number: 8283105
    Abstract: A positive resist composition including a base component (A) which exhibits increased solubility in an alkali developing solution under action of acid and an acid-generator component (B) which generates acid upon exposure, the component (A) including a polymeric compound (A1) having an acid dissociable, dissolution inhibiting group in the structure thereof and including a structural unit (a0) having an —SO2— containing cyclic group on the terminal of the side chain, and the component (B) including an acid generator (B1) containing a compound represented by general formula (b1-1) (R0 represents a hydrocarbon group of 1 to 12 carbon atoms which may have a substituent, provided that the carbon atom adjacent to the sulfur atom within the —SO3? group has no fluorine atom bonded thereto, and Z+ represents an organic cation).
    Type: Grant
    Filed: March 4, 2010
    Date of Patent: October 9, 2012
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Yasuhiko Kakinoya, Naoto Motoike
  • Patent number: 8283102
    Abstract: Disclosed are a photoacid generator, a copolymer, a chemically amplified resist composition, and a method of forming a pattern using the chemically amplified resist composition. The photoacid is connected with a main chain of the copolymer, whereby the photoacid is equally dispersed within a resist layer, and characteristics of line edge roughness of a resist pattern is improved.
    Type: Grant
    Filed: April 2, 2009
    Date of Patent: October 9, 2012
    Assignee: Korea Kumho Petrochemical Co., Ltd.
    Inventors: Jung Hoon Oh, Sang Jin Kim, Jin Ho Kim, Dae Hyeon Shin
  • Patent number: 8278023
    Abstract: A salt represented by the formula (I-BB): 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 C4-C36 alicyclic hydrocarbon group which has one or more —OXa groups and which is not capable of being eliminated by the action of an acid etc., and Xa represents a hydrogen atom or 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.
    Type: Grant
    Filed: May 25, 2010
    Date of Patent: October 2, 2012
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Masako Sugihara, Tatsuro Masuyama
  • Patent number: 8257904
    Abstract: A resist composition including: a base component (A) which exhibits changed solubility in an alkali developing solution under action of an acid; an acid generator component (B) which generates an acid upon exposure; and an organic solvent (S), wherein the base component (A) includes a polymeric compound (A1) which contains a structural unit (a0) represented by the general formula (a0-1) shown below: [Chemical Formula 1] (in the formula, R1 represents a hydrogen atom, a lower alkyl group, or a halogenated lower alkyl group; R2 represents a bivalent linking group; and R3 represents a cyclic group which has —SO2— within the ring skeleton), and the organic solvent (S) includes a cyclic ketone having a 5 to 7-membered ring or an ether represented by the general formula (S-1) shown below: [Chemical Formula 2] (in the formula, R4 represents an alkyl group of 1 to 5 carbon atoms; R5 represents an alkyl group of 1 to 3 carbon atoms; and n represents an integer of 0 to 2).
    Type: Grant
    Filed: November 10, 2009
    Date of Patent: September 4, 2012
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Naoto Motoike, Yasuhiko Kakinoya
  • Patent number: 8252504
    Abstract: A polymer obtained through copolymerization of a monomer having a hexafluoroalcohol pendant whose hydroxyl moiety has been protected and a monomer having an acid labile group is useful as an additive to a photoresist composition for immersion lithography. When processed by immersion lithography, the resist composition exhibits good water repellency and water slip and produces few development defects.
    Type: Grant
    Filed: February 13, 2009
    Date of Patent: August 28, 2012
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Yuji Harada, Jun Hatakeyama, Kazunori Maeda, Tomohiro Kobayashi
  • Patent number: 8252508
    Abstract: A positive photosensitive composition comprises: (A) 5 to 20 parts by weight of the total amount of at least one compound that generates an acid upon irradiation with an actinic ray; and (B) 100 parts by weight of the total amount of at least one fluorine atom-containing resin having a group that increases a solubility of the resin in an alkaline developer by the action of an acid.
    Type: Grant
    Filed: June 21, 2010
    Date of Patent: August 28, 2012
    Assignee: FUJIFILM Corporation
    Inventor: Kunihiko Kodama
  • Patent number: 8252505
    Abstract: A resist composition including a base component (A) that exhibits changed solubility in an alkali developing solution under the action of acid, and an acid generator component (B) that generates acid upon exposure, wherein the acid generator component (B) includes an acid generator (B1) consisting of a compound represented by general formula (b1-2) shown below: [Chemical Formula 1] A+Z???(b1-2) wherein A+ represents an organic cation; and Z? represents an anionic cyclic group, wherein the cyclic group includes an ester linkage within the ring structure, two mutually different groups are bonded to the ring structure, one of these groups includes an ester linkage in which a carbon atom that constitutes part of the ester linkage is bonded directly to the ring structure, and the other group includes an anion moiety.
    Type: Grant
    Filed: February 16, 2009
    Date of Patent: August 28, 2012
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Akiya Kawaue, Keita Ishiduka, Kensuke Matsuzawa, Yoshiyuki Utsumi, Hiroaki Shimizu
  • Patent number: 8252503
    Abstract: Photoresist compositions are disclosed.
    Type: Grant
    Filed: August 24, 2007
    Date of Patent: August 28, 2012
    Assignee: AZ Electronic Materials USA Corp.
    Inventors: Srinivasan Chakrapani, Munirathna Padmanaban, Muthiah Thiyagarajan, Takanori Kudo, David L. Rentkiewicz
  • Patent number: 8247160
    Abstract: A resist composition including a base component that exhibits changed solubility in an alkali developing solution under the action of acid, and an acid generator consisting of a compound represented by general formula (b1). In formula (b1), Y1 represents a fluorinated alkylene group of 1 to 4 carbon atoms, X represents an aliphatic cyclic group of 3 to 30 carbon atoms, R11? to R13? each represents an aryl group or alkyl group, provided that at least one of R11? to R13? is an aryl group having a substituent represented by general formula (b1-0), and two alkyl groups among R11? to R13? may be bonded to each other to form a ring with the sulfur atom in the formula. In formula (b1-0), R52 represents a chain-like or cyclic hydrocarbon group, and f and g each represents 0 or 1.
    Type: Grant
    Filed: July 13, 2009
    Date of Patent: August 21, 2012
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Yoshiyuki Utsumi, Keita Ishiduka, Kensuke Matsuzawa, Akiya Kawaue, Hiroaki Shimizu, Tsuyoshi Nakamura
  • Patent number: 8247161
    Abstract: A resist composition for immersion exposure including: a base component (A) which exhibits changed solubility in an alkali developing solution under the action of acid; an acid-generator component (B) which generates acid upon exposure; and a fluorine-containing resin component (F); dissolved in an organic solvent (S), the fluorine-containing resin component (F) including a structural unit (f1) containing a fluorine atom, a structural unit (f2) containing a hydrophilic group-containing aliphatic hydrocarbon group, and a structural unit (f3) derived from an acrylate ester containing a tertiary alkyl group-containing group or an alkoxyalkyl group.
    Type: Grant
    Filed: October 5, 2009
    Date of Patent: August 21, 2012
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Masaru Takeshita, Yasuhiro Yoshii
  • Patent number: 8247159
    Abstract: A positive resist composition including a resin component (A) which exhibits increased alkali solubility under action of acid and an acid-generator component (B) which generates acid upon exposure, the resin component (A) including a structural unit (a0) represented by general formula (a0) shown below and a structural unit (a1) derived from an acrylate ester having a polycyclic group-containing, acid dissociable, dissolution inhibiting group of a tertiary alkyl ester-type: wherein: R represents a hydrogen atom, a halogen atom, a lower alkyl group or a halogenated lower alkyl group; Y1 represents an aliphatic cyclic group; Z represents a tertiary alkyl group-containing group; a represents an integer of 1 to 3, and b represents an integer of 0 to 2, such that a+b=1 to 3; and each of c, d and e independently represents an integer of 0 to 3.
    Type: Grant
    Filed: April 18, 2007
    Date of Patent: August 21, 2012
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Masaru Takeshita, Ryoji Watanabe
  • Patent number: 8247162
    Abstract: A method of forming a pattern and a photoresist composition, the method including forming a photoresist film on a substrate by coating a photoresist composition thereon, the photoresist composition including a polymerized photoresist additive, a polymer including an acid-labile protective group at a side chain, a photoacid generator, and a solvent; exposing the photoresist film; and forming a photoresist pattern by developing the photoresist film using an aqueous alkali developer, wherein the polymerized photoresist additive includes a hydrophilic repeating unit having an aliphatic hydrocarbon backbone and a side chain containing an oxygen heteroatom in a heterocyclic ring substituted with at least three hydroxyl groups, and a hydrophobic repeating unit having an aliphatic hydrocarbon backbone and a side chain containing a fluorinated aliphatic hydrocarbon group.
    Type: Grant
    Filed: April 19, 2010
    Date of Patent: August 21, 2012
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Ji-Man Park, Young-Ho Kim, Hyo-Jin Yun, Sun-Yul Ahn, Song-Se Yi, Kyung-Woo Park
  • Patent number: 8241831
    Abstract: An acid generating agent represented by the following formula (1) or (2) is provided, which is included in chemically amplified resist compositions: wherein in the formula (1) and (2), X represents an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms and selected from alkyl, haloalkyl and alkylsulfonyl, which may have at least one hydrogen atom substituted by an ether group, an ester group, a carbonyl group, an acetal group, a nitrile group, a cyano group, a hydroxyl group, a carboxyl group or an aldehyde group, or represents a perfluoroalkyl group having 1 to 4 carbon atoms; R6 represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or a heteroatom selected from nitrogen, sulfur, fluorine and oxygen; m is an integer from 0 to 2; and A+ is an organic counterion.
    Type: Grant
    Filed: September 5, 2008
    Date of Patent: August 14, 2012
    Assignee: Korea Kumho Petrochemical Co., Ltd.
    Inventors: Sung-Do Jung, Jin-Ho Kim, Jung-Hoon Oh, Hyun-Soon Lim