Polyolefin Or Halogen Containing Patents (Class 430/907)
  • Patent number: 8592622
    Abstract: A polymerizable fluorine-containing compound represented by formula (1), wherein R1 represents a polymerizable double-bond containing group, R2 represents an acid-labile protecting 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 R2, 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 resist composition capable of forming a pattern that is transparent to exposure light and superior in rectangularity.
    Type: Grant
    Filed: January 4, 2011
    Date of Patent: November 26, 2013
    Assignee: Central Glass Company, Limited
    Inventors: Yoshimi Isono, Jonathan Joachim Jodry, Satoru Narizuka
  • Patent number: 8580486
    Abstract: There is provided an acid having a fluorine-containing carbanion structure or a salt having a fluorine-containing carbanion structure, which is represented by the following general formula (1). By using a photoacid generator for chemically amplified resist materials that generates this acid, it is possible to provide a photoacid generator which has a high sensitivity to the ArF excimer laser light or the like, of which acid (photo generated acid) to be generated has a sufficiently high acidity, and which has a high dissolution in resist solvent and a superior compatibility with resin, and a resist material containing such a photoacid generator.
    Type: Grant
    Filed: March 10, 2009
    Date of Patent: November 12, 2013
    Assignee: Central Glass Company, Limited
    Inventors: Masashi Nagamori, Satoru Narizuka, Susumu Inoue, Takashi Kume
  • Patent number: 8574812
    Abstract: A resist composition of the invention includes: (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, A1, R2, Q1, Q2, L1, ring W1, and Z+ are defined in the specification.
    Type: Grant
    Filed: February 24, 2012
    Date of Patent: November 5, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Satoshi Yamaguchi
  • Patent number: 8574817
    Abstract: A positive resist composition comprising a polymer having carboxyl groups substituted with an acid labile group having formula (1), (2) or (3) exhibits a high contrast of alkaline dissolution rate before and after exposure, a high resolution, a reduced acid diffusion rate, and forms a pattern with good profile, minimal edge roughness, and etch resistance. In formula (1), R1, R2, R5, R6, R8, and R9 are alkyl, aryl, or alkenyl, R3, R4, R7, R10, and R11 are hydrogen, alkyl, alkoxy, acyloxy, halogen, cyano, nitro, hydroxyl or trifluoromethyl, M is methylene or ethylene, R is a single bond or linking group.
    Type: Grant
    Filed: September 13, 2012
    Date of Patent: November 5, 2013
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Koji Hasegawa
  • Patent number: 8574813
    Abstract: A resist composition for immersion exposure and a method of forming a resist pattern 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: May 10, 2012
    Date of Patent: November 5, 2013
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventor: Makiko Irie
  • Patent number: 8563219
    Abstract: A resist composition containing; (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, (B) an acid generator, and (D) a salt having an anion represented by the formula (IA), wherein R1, A1, R2, R1A and R2A are defined in the specification.
    Type: Grant
    Filed: February 24, 2012
    Date of Patent: October 22, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Tatsuro Masuyama, Satoshi Yamaguchi
  • Patent number: 8563218
    Abstract: A resist composition of the present invention has (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, (B) an acid generator and (D) a compound 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 in each occurrence independently represent a C1 to C12 hydrocarbon group, a C1 to C6 alkoxyl group, a C2 to C7 acyl group, a C2 to C7 acyloxy group, a C2 to C7 alkoxycarbonyl group, a nitro group or a halogen atom; m? and n? independently represent an integer of 0 to 4.
    Type: Grant
    Filed: February 24, 2012
    Date of Patent: October 22, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Takahiro Yasue
  • Patent number: 8563217
    Abstract: A resist composition having; (A1) a resin having a structural unit represented by the formula (I), (A2) a resin having a structural unit represented by the formula (II) and 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, wherein R1, A1, R2, R3, and ring X1 are defined in the specification.
    Type: Grant
    Filed: February 24, 2012
    Date of Patent: October 22, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Akira Kamabuchi
  • Patent number: 8551684
    Abstract: A polymer for forming a resist protection film which is used in a liquid immersion lithography process to protect a photoresist layer, a composition for forming a resist protection film, and a method of forming a pattern of a semiconductor device using the composition are disclosed. The polymer for forming a resist protection film includes a repeating unit represented by Formula 1 below. In Formula 1, R1 is a hydrogen atom (H), a fluorine atom (F), a methyl group (—CH3), a C1-C20 fluoroalkyl group, or a C1-C5 hydroxyalkyl group, R2 is a C1-C10 linear or branched alkylene group or alkylidene group, or a C5-C10 cycloalkylene group or cycloalkylidene group, X is wherein n is an integer of 0 to 5 and * denotes the remaining moiety of Formula 1 after excluding X, and m, the stoichiometric coefficient of X, is 1 or 2.
    Type: Grant
    Filed: June 30, 2011
    Date of Patent: October 8, 2013
    Assignee: Dongjin Semichem Co., Ltd.
    Inventors: Jong Kyoung Park, Man Ho Han, Hyun Jin Kim, Deog Bae Kim
  • Patent number: 8535871
    Abstract: A radiation-sensitive resin composition includes a first polymer that includes a repeating unit having an acid-labile group and becomes alkali-soluble upon dissociation of the acid-labile group, and a radiation-sensitive acid-generating agent. The acid-labile group has a structure shown by a general formula (1). R1 represents a methyl group or the like, R2 represents a hydrocarbon group that forms a cyclic structure, R3 represents a fluorine atom or the like, R4 represents a carbon atom, and n1 is an integer from 1 to 7.
    Type: Grant
    Filed: December 14, 2011
    Date of Patent: September 17, 2013
    Assignee: JSR Corporation
    Inventors: Yuusuke Asano, Takanori Kawakami
  • Patent number: 8530136
    Abstract: Phenolic molecular glasses such as calixarenes include at least one fluoroalcohol containing unit. The fluoroalcohol containing molecular glasses can be used in photoresist compositions. Also disclosed are processes for generating a resist image on a substrate using the photoresist composition.
    Type: Grant
    Filed: December 17, 2010
    Date of Patent: September 10, 2013
    Assignee: International Business Machines Corporation
    Inventors: Luisa D. Bozano, Gregory Breyta, Ekmini A. DeSilva, William D. Hinsberg, Ratnam Sooriyakumaran, Linda K. Sundberg
  • Patent number: 8524440
    Abstract: The present invention provides a photoresist composition comprising a resin which comprises a structural unit represented by the formula (I): wherein Q1 and Q2 independently represent a fluorine atom etc., U represents a C1-C20 divalent hydrocarbon group etc., X1 represents —O—CO— etc., and A+ represents an organic counter ion, and a compound represented by the formula (D?): wherein R51, R52, R53 and R54 independently represent a C1-C20 alkyl group etc., and A11 represents a C1-C36 saturated cyclic hydrocarbon group which may have one or more substituents and which may contain one or more heteroatoms.
    Type: Grant
    Filed: January 3, 2011
    Date of Patent: September 3, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yuko Yamashita, Nobuo Ando
  • Patent number: 8518628
    Abstract: A material is provided for use in an immersion lithographic process of a semiconductor substrate. The material includes a photo-sensitive polymer configured to turn soluble to a base solution in response to reaction with an acid and at least one of either a base soluble polymer or an acid labile polymer. The base soluble polymer is configured to turn soluble to water in response to reaction with a developer solution. The acid labile polymer is configured to turn soluble to water after releasing a leaving group in reaction to the acid.
    Type: Grant
    Filed: September 22, 2006
    Date of Patent: August 27, 2013
    Assignee: Taiwan Semiconductor Manufacturing Company, Ltd.
    Inventors: Ching-Yu Chang, Chih-Cheng Chiu
  • Patent number: 8518629
    Abstract: A resist composition for immersion exposure, including a base component (A) that exhibits changed solubility in an alkali developing solution under action of acid, an acid generator component (B) that generates acid upon exposure, and a fluorine-containing compound (C) represented by general formula (c-1) (in formula (c-1), R1 represents an organic group which may contain a polymerizable group; X represents a divalent organic group having an acid dissociable portion; and R2 represents an organic group having a fluorine atom).
    Type: Grant
    Filed: August 26, 2011
    Date of Patent: August 27, 2013
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Tsuyoshi Kurosawa, Hiroaki Shimizu
  • Patent number: 8507176
    Abstract: Provided are radiation-sensitive polymers and compositions which may be used in photolithographic processes. The polymers and compositions provide enhanced sensitivity to activating radiation.
    Type: Grant
    Filed: December 30, 2010
    Date of Patent: August 13, 2013
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: James W. Thackeray, Emad Aqad
  • Patent number: 8486606
    Abstract: An acrylate derivative represented by the following general formula (1): (in the formula, R1 represents a hydrogen atom, a methyl group or a trifluoromethyl group; each of R2, R3, R5, R7, R8, R9 and R10 independently represents a hydrogen atom, an alkyl group, a cycloalkyl group or an alkoxy group; each of R4 and R6 independently represents a hydrogen atom, an alkyl group, a cycloalkyl group or an alkoxy group, or R4 and R6 are bonded to each other to represent an alkylene group, —O— or —S—; n represents 0, 1 or 2; and W represents an alkylene group or a cycloalkylene group); an intermediate thereof; a method for producing the same; a polymer compound which is obtainable from polymerization of a raw material containing the foregoing acrylate derivative and which is excellent in solubility in an organic solvent used for the preparation of a photoresist composition; and a photoresist composition containing the polymer compound, an organic solvent and a photo acid generator and having excellent adhesion to s
    Type: Grant
    Filed: June 30, 2009
    Date of Patent: July 16, 2013
    Assignee: Kuraray Co., Ltd.
    Inventors: Junko Sato, Osamu Nakayama, Takashi Fukumoto
  • Patent number: 8475997
    Abstract: A resist composition for immersion exposure including: a fluorine-containing polymeric compound (F) containing a structural unit (f1) having a base dissociable group and a structural unit (f2) represented by general formula (f2-1) (wherein R represents a hydrogen atom, a lower alkyl group or a halogenated lower alkyl group; and W is a group represented by any one of general formulas (w-1) to (w-4)); 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.
    Type: Grant
    Filed: December 23, 2011
    Date of Patent: July 2, 2013
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Daiju Shiono, Tomoyuki Hirano, Sanae Furuya, Takahiro Dazai, Hiroaki Shimizu, Tsuyoshi Kurosawa, Hideto Nito, Tsuyoshi Nakamura
  • Patent number: 8470513
    Abstract: A radiation-sensitive resin composition includes a polymer that includes at least one repeating unit (i) selected from a repeating unit shown by a formula (1), (2), and (3); and a repeating unit (ii) shown by a formula (4). R1 represents a hydrogen atom or a methyl group. Each R2 independently represents one of a linear or branched alkyl group having 1 to 12 carbon atoms, a linear or branched alkoxy group having 1 to 12 carbon atoms, and an alicyclic hydrocarbon group having 3 to 25 carbon atoms. p is an integer from 0 to 3, and q is an integer from 1 to 3, and p+q?5. A chemically-amplified positive-tone resist film that is sensitive to extreme ultraviolet rays (EUV) can be formed using the radiation-sensitive resin composition.
    Type: Grant
    Filed: September 23, 2011
    Date of Patent: June 25, 2013
    Assignee: JSR Corporation
    Inventors: Kota Nishino, Ken Maruyama, Daisuke Shimizu, Toshiyuki Kai
  • Patent number: 8460856
    Abstract: A photosensitive material for use in semiconductor manufacture comprises a copolymer that includes a plurality of photoresist chains and a plurality of hydrophobic chains, each hydrophobic chain attached to the end of one of the photoresist chains. The copolymer in response to externally applied energy will self-assemble to a photoresist layer and a hydrophobic layer.
    Type: Grant
    Filed: September 21, 2011
    Date of Patent: June 11, 2013
    Assignee: Taiwan Semiconductor Manufacturing Company, Ltd.
    Inventors: Hsiao-Wei Yeh, Jen-Chieh Shih, Jian-Hong Chen
  • Patent number: 8450041
    Abstract: An actinic ray-sensitive or radiation-sensitive resin composition includes (A) a compound capable of generating a specific acid having a norbornyl structure upon irradiation with an actinic ray or radiation, and (B) a resin capable of increasing the dissolution rate of the resin (B) in an alkali developer by an action of an acid, the resin (B) containing a specific repeating unit having a lactone structure on the resin side chain through a linking group, and a pattern forming method uses the composition.
    Type: Grant
    Filed: January 15, 2010
    Date of Patent: May 28, 2013
    Assignee: FUJIFILM Corporation
    Inventor: Shuhei Yamaguchi
  • Patent number: 8450044
    Abstract: A positive resist composition including a resin component (A) which exhibits increased solubility in an alkali developing solution under the action of acid and an acid-generator component (B), the resin component (A) including a polymeric compound (A1) having a structural unit (a1) containing an acid dissociable, dissolution inhibiting group, a structural unit (a5) containing a base dissociable group an a structural unit (a6) represented by general formula (a6-1) (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; each of R2 and R3 independently represents a hydrogen atom or an alkyl group that may contain an oxygen atom at an arbitrary position, or R2 and R3 are bonded together to form an alkylene group; and W represents a cyclic alkylene group that may include an oxygen atom at an arbitrary position).
    Type: Grant
    Filed: November 12, 2010
    Date of Patent: May 28, 2013
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Tomoyuki Hirano, Daiju Shiono, Daichi Takaki
  • 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: 8431323
    Abstract: A fluorinated monomer of cyclic acetal structure has formula (1) wherein R is a C1-C20 alkyl group which may be substituted with halogen or separated by oxygen or carbonyl, and Z is a divalent organic group which forms a ring with alkylenoxy and contains a polymerizable unsaturated group. A polymer derived from the fluorinated monomer may be endowed with appropriate water repellency, water sliding property, lipophilicity, acid lability and hydrolyzability and is useful in formulating a protective coating composition and a resist composition.
    Type: Grant
    Filed: October 29, 2009
    Date of Patent: April 30, 2013
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takeru Watanabe, Satoshi Shinachi, Takeshi Kinsho, Koji Hasegawa, Yuji Harada, Jun Hatakeyama, Kazunori Maeda, Tomohiro Kobayashi
  • Patent number: 8426103
    Abstract: A positive resist composition for use with electron beam, X-ray or EUV and a pattern forming method using the positive resist composition are provided, the positive resist composition including: (A) a resin capable of decomposing under an action of an acid to increase a dissolution rate in an aqueous alkali solution; (B) a compound capable of generating an acid upon irradiation with actinic rays or radiation; (C) a basic compound; and (D) an organic solvent, wherein the entire solid content concentration in the resist composition is from 1.0 to 4.5 mass % and a ratio of (B) the compound capable of generating an acid upon irradiation with actinic rays or radiation is from 10 to 50 mass % based on the entire solid content.
    Type: Grant
    Filed: February 12, 2009
    Date of Patent: April 23, 2013
    Assignee: FUJIFILM Corporation
    Inventor: Katsuhiro Yamashita
  • 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: 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: 8389201
    Abstract: The present invention relates to a positive resist composition and to a pattern forming process using the same. The present invention provides: a positive resist composition having an enhanced etching resistance and an excellent resolution and being capable of providing an excellent pattern profile even at a substrate-side boundary face of resist, in photolithography for fine processing, and particularly in lithography adopting, as an exposure source, KrF laser, extreme ultraviolet rays, electron beam, X-rays, or the like; and a pattern forming process utilizing the positive resist composition.
    Type: Grant
    Filed: May 24, 2010
    Date of Patent: March 5, 2013
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Akinobu Tanaka, Keiichi Masunaga, Daisuke Domon, Satoshi Watanabe
  • 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: 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: 8343694
    Abstract: A photomask blank has a resist film comprising (A) a base resin, (B) an acid generator, and (C) a basic compound. The resist film further comprises (D) a polymer comprising recurring units having a side chain having a fluorinated hydrocarbon group which contains a carbon atom to which a hydroxyl group is bonded and vicinal carbon atoms bonded thereto, the vicinal carbon atoms having in total at least two fluorine atoms bonded thereto. Addition of polymer (D) ensures uniform development throughout the resist film, enabling to form a resist pattern having high CD uniformity.
    Type: Grant
    Filed: August 11, 2011
    Date of Patent: January 1, 2013
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Ryuji Koitabashi, Satoshi Watanabe, Takanobu Takeda, Keiichi Masunaga, Tamotsu Watanabe
  • Patent number: 8334088
    Abstract: Linear or branched functionalized polycarbosilanes having an absorbance less than 3.0 ?m?1 at 193 nm and a relatively high refractive index are provided. The functionalized polycarbosilanes contain at least one pendant group that is acid labile or aqueous base soluble. Also disclosed are photoresists formulations containing the functionalized polycarbosilanes that are suitable for use in lithography, e.g., immersion lithography.
    Type: Grant
    Filed: November 3, 2010
    Date of Patent: December 18, 2012
    Assignee: International Business Machines Corporation
    Inventors: Robert D. Allen, Matthew E. Colburn, Daniel P. Sanders, Ratnam Sooriyakumaran, Hoa D. Truong
  • 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: 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: 8288072
    Abstract: A resist lower layer film composition, wherein an etching speed is fast, thus an etching time period can be shortened to minimize a film thickness loss of a resist pattern and a deformation of the pattern during etching, therefore, a pattern can be transferred with high accuracy and an excellent pattern can be formed on a substrate is provided. The resist lower layer film composition comprising at least a polymer having a repeating unit represented by the following general formula (1).
    Type: Grant
    Filed: February 26, 2008
    Date of Patent: October 16, 2012
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Kazumi Noda, Seiichiro Tachibana, Takeshi Kinsho, Tsutomu Ogihara
  • 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: 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: 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: 8221956
    Abstract: A resist composition for immersion exposure including: a fluorine-containing polymeric compound (F) containing a structural unit (f1) having a base dissociable group and a structural unit (f2) represented by general formula (f2-1) (wherein R represents a hydrogen atom, a lower alkyl group or a halogenated lower alkyl group; and W is a group represented by any one of general formulas (w-1) to (w-4)); 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.
    Type: Grant
    Filed: June 18, 2009
    Date of Patent: July 17, 2012
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Daiju Shiono, Tomoyuki Hirano, Sanae Furuya, Takahiro Dazai, Hiroaki Shimizu, Tsuyoshi Kurosawa, Hideto Nito, Tsuyoshi Nakamura
  • 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: 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: 8173354
    Abstract: A sulfonium salt having a triphenylsulfonium cation and a sulfite anion within the molecule is best suited as a photoacid generator in chemically amplified resist compositions. Upon exposure to high-energy radiation, the sulfonium salt generates a sulfonic acid, which facilitates efficient scission of acid labile groups in chemically amplified positive resist compositions. Because of substantial non-volatility under high vacuum conditions in the EB or EUV lithography, the risk of the exposure tool being contaminated is minimized.
    Type: Grant
    Filed: July 7, 2010
    Date of Patent: May 8, 2012
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Masaki Ohashi
  • Patent number: 8168366
    Abstract: The present invention relates to a radiation sensitive photoresist composition. The composition comprises a polymer comprising at least two monomers. The first monomer has an acid cleavable tertiary ester group. The second monomer is an acidic monomer. The acid cleavable ester group of the polymer has a surprisingly low activation energy which results in improved resist images in lithographic processes.
    Type: Grant
    Filed: October 16, 2008
    Date of Patent: May 1, 2012
    Assignee: International Business Machines Corporation
    Inventors: Robert David Allen, Richard Anthony DiPietro, Ratnam Sooriyakumaran, Hoa D Truong
  • Patent number: 8163461
    Abstract: The invention provides various photoacid generator compounds and ionic components thereof. Photoresist compositions that include the ions and non-ionic photoacid generator compounds are also provided. The invention further provides methods of making and using the photoacid generator compounds and photoresist compositions disclosed herein. The compounds and compositions are useful as photoactive components in chemically amplified resist compositions for use in, for example, various microfabrication applications.
    Type: Grant
    Filed: April 9, 2009
    Date of Patent: April 24, 2012
    Assignee: Cornell Research Foundation, Inc.
    Inventors: Christopher K. Ober, Yi Yi
  • Patent number: 8158330
    Abstract: A protective coating composition comprising a copolymer of an alkali-soluble (?-trifluoromethyl) acrylate and a norbornene derivative as a base polymer, optionally in admixture with a second polymer containing sulfonic acid and/or sulfonic acid amine salt in repeat units is applied onto a resist film. The protective coating is effective in minimizing development defects and forming a resist pattern of improved profile.
    Type: Grant
    Filed: May 11, 2009
    Date of Patent: April 17, 2012
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Yuji Harada, Jun Hatakeyama, Koji Hasegawa, Satoshi Shinachi
  • Patent number: 8158325
    Abstract: Overcoating layer compositions that are applied above a photoresist composition including for immersion lithography processing as well as non-immersion imaging.
    Type: Grant
    Filed: October 3, 2006
    Date of Patent: April 17, 2012
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: Deyan Wang, Cheng-Bai Xu