Polymer Of Unsaturated Acid Or Ester Patents (Class 430/910)
  • Patent number: 7745098
    Abstract: A polymer compound having a structural unit (a0) represented by a general formula (a0-1) shown below, and a structural unit (a1) that is derived from an acrylate ester containing an acid dissociable, dissolution inhibiting group but is not classified as said structural unit (a0).
    Type: Grant
    Filed: August 26, 2008
    Date of Patent: June 29, 2010
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Takahiro Dazai, Takayoshi Mori, Hiroaki Shimizu, Kyoko Ohshita, Komei Hirahara
  • Patent number: 7741009
    Abstract: A positive resist composition including a resin component (A) which exhibits increased solubility in an alkali developing solution under action of acid and has a structural unit (a1) represented by general formula (a1-0-2) shown below, and an acid-generator component (B) which generates acid upon exposure and includes an acid generator (B1) consisting of a compound represented by general formula (b1-12) shown below: wherein R represents a hydrogen atom, a lower alkyl group or a halogenated lower alkyl group; X2 represents an acid dissociable, dissolution inhibiting group; and Y2 represents an alkylene group or a divalent aliphatic cyclic group; and R2—O—Y1—SO3?A+??(b1-12) wherein R2 represents a monovalent aromatic organic group; Y1 represents an alkylene group of 1 to 4 carbon atoms which may be substituted with a fluorine atom; and A+ represents a cation.
    Type: Grant
    Filed: July 17, 2008
    Date of Patent: June 22, 2010
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Takahiro Dazai, Hiroaki Shimizu, Kyoko Ohshita, Komei Hirahara
  • Patent number: 7741015
    Abstract: A pattern is formed by applying a positive resist composition comprising a polymer comprising 7-oxanorbornane ring-bearing recurring units and acid labile group-bearing recurring units and an acid generator onto a substrate to form a resist film, heat treating and exposing the resist film to radiation, heat treating and developing the resist film with a developer, and causing the resist film to crosslink and cure with the aid of acid and/or heat. A second resist pattern is then formed in the space area of the first resist pattern. The double patterning process reduces the pitch between patterns to one half.
    Type: Grant
    Filed: February 12, 2008
    Date of Patent: June 22, 2010
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Takao Yoshihara, Takeshi Kinsho, Koji Hasegawa, Yoshio Kawai, Katsuya Takemura
  • Patent number: 7741008
    Abstract: Disclosed is a positive resist composition comprising a resin component (A) and an acid generator component (B), wherein the component (A) contains a polymer compound (A1) containing a structural unit (a0) represented by formula (a0) shown below and a structural unit (a2) derived from an acrylate ester containing a lactone-containing cyclic group: (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 an acid dissociable, dissolution inhibiting group containing a tertiary alkyl group; a represents an integer from 1 to 3, b represents an integer from 0 to 2, and a+b=1 to 3; and c, d and e each represents, independently, an integer from 0 to 3).
    Type: Grant
    Filed: October 17, 2006
    Date of Patent: June 22, 2010
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Sanae Furuya, Hideo Hada, Yusuke Nakagawa, Akiyoshi Yamazaki
  • Patent number: 7741007
    Abstract: The present invention provides a chemically amplified resist composition comprising: (A) a salt represented by the formula (1) wherein R21, Q1, Q2, and A+ defined in the specification; (B) a salt represented by the formula (II): wherein R22, Q3, Q4, and A?+ are defined in the specification; and (C) a resin which contains a structural unit having a structural unit having an acid-labile group and 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.
    Type: Grant
    Filed: December 3, 2007
    Date of Patent: June 22, 2010
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Satoshi Yamaguchi, Satoshi Yamamoto, Nobuo Ando
  • Patent number: 7741380
    Abstract: The invention provides (1) an ink composition including a polymerization initiator and at least one compound selected from the group consisting of (meth)acrylic acid and monofunctional (meth)acrylic acid esters and amides each having a carboxy group in the molecule, (2) an ink composition including a polymerization initiator, at least one compound selected from the group consisting of (meth)acrylic acid and monofunctional (meth)acrylic acid esters and amides each having a carboxy group in the molecule, and a monofunctional (meth)acrylic acid ester or amide having an alkylene oxide repeating unit in the molecule, and (3) an ink composition including a polymerization initiator and a monofunctional (meth)acrylic acid ester or amide having a basic group in the molecule; and an ink jet recording method, a method for producing a planographic printing plate and a planographic printing plate produced by the method for producing a planographic printing plate using the above-mentioned ink compositions.
    Type: Grant
    Filed: September 27, 2006
    Date of Patent: June 22, 2010
    Assignee: FUJIFILM Corporation
    Inventor: Ippei Nakamura
  • Patent number: 7736842
    Abstract: A resist composition for electron beam or extreme ultraviolet (EUV), comprising a resin component (A) which exhibits changed alkali solubility under action of acid, and a photoacid generator component (B) that generates acid on exposure, wherein the component (B) comprises at least one onium salt selected from the group consisting of onium salts having an anion represented by formula (b-0-1) or (b-0-2) shown below: wherein X represents an alkylene group having 2 to 6 carbon atoms, in which at least one hydrogen atom is substituted with a fluorine atom; and each of Y and Z independently represents an alkyl group having 1 to 10 atoms, in which at least one hydrogen atom is substituted with a fluorine atom.
    Type: Grant
    Filed: September 1, 2005
    Date of Patent: June 15, 2010
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hideo Hada, Daiju Shiono, Hiroo Kinoshita, Takeo Watanabe
  • Patent number: 7727704
    Abstract: In a positive resist composition comprising (A) a resin component which becomes soluble in an alkaline developer under the action of an acid and (B) a photoacid generator, component (A) is a polymer of formula (1) wherein R1 is H, methyl or trifluoromethyl, R2 and R3 are alkyl, R4 is a monovalent hydrocarbon group, X1 is O, S or CH2CH2, X2 is O, S, CH2 or CH2CH2, n is 1 or 2, a1, a2, c, d1 and d2 each are from 0 to less than 1, b is from 0.01 to less than 1, and a1+a2+b+c+d1+d2=1. The resist composition forms a pattern with high rectangularity at an enhanced resolution when processed by ArF lithography.
    Type: Grant
    Filed: July 5, 2007
    Date of Patent: June 1, 2010
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Ryosuke Taniguchi, Tsunehiro Nishi, Tomohiro Kobayashi
  • Patent number: 7723007
    Abstract: The present invention provides a polymer compound which can constitute a photoresist composition which is capable of having an excellent resolution, forming a fine pattern with a good rectangularity, obtaining favorable resist characteristics even when acid strength of a acid generated from an acid generator is weak, and having favorable sensitivity; a photoresist composition including the polymer compound; and a resist pattern formation method using the photoresist composition.
    Type: Grant
    Filed: January 28, 2005
    Date of Patent: May 25, 2010
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Toshiyuki Ogata, Syogo Matsumaru, Yohei Kinoshita, Hideo Hada, Daiju Shiono, Hiroaki Shimizu, Naotaka Kubota
  • Patent number: 7718342
    Abstract: A polymer is provided comprising recurring units having formulas (1), (2), (3), (4), (5), and (6) in amounts of 1-60 mol % (1), 1-60 mol % (2), 1-50 mol % (3), 0-60 mol % (4), 0-30 mol % (5), and 0-30 mol % (6), and having a Mw of 3,000-30,000 and a Mw/Mn of 1.5-2.5. R1, R3, R4, R7, R9, and R11 are H or CH3, Y is methylene or O, R2 is CO2R10 when Y is methylene and R2 is H or CO2R10 when Y is O, R10 is C1-C15 alkyl which may be separated by O, R5 and R6 are H or OH, R8 is a tertiary ester type acid-labile protective group, and R12 is OH-containing fluoroalkyl. A resist composition comprising the polymer has a high resolution and is improved in line edge roughness and I/G bias.
    Type: Grant
    Filed: December 27, 2006
    Date of Patent: May 18, 2010
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Kenji Funatsu, Tomohiro Kobayashi, Koji Hasegawa, Tsunehiro Nishi
  • Patent number: 7704669
    Abstract: To provide a resist which is excellent in the solubility in a resist solvent and little dependent on baking temperature and can form developed patterns reduced in line edge roughness. An acrylic polymer characterized by comprising units of the general formula (1), units of general formula (2), and units of general formula (3) and/or units of general formula (4), wherein R, R?, R? and R?? are each hydrogen, methyl, or trifluoromethyl; R1 is hydrogen, C1-4 linear or branched alkyl, alkoxy, or C1-4 linear or branched fluoroalkyl; X is a C7-20 polycyclic aliphatic hydrocarbon group consisting of carbon atoms and hydrogen atoms; R2 and R3 are each independently C1-4 linear or branched alkyl; R4 is a C4-20 alicyclic hydrocarbon group; R5 is C1-4 linear or branched alkyl; and R6 and R7 are each hydrogen or C1-4 linear or branched alkyl.
    Type: Grant
    Filed: August 4, 2004
    Date of Patent: April 27, 2010
    Assignee: JSR Corporation
    Inventors: Kouichi Fujiwara, Hiroshi Yamaguchi, Atsushi Nakamura
  • Patent number: 7700256
    Abstract: The present invention relates to new polymers that contain repeat units of phenol and photoacid-labile esters that contain an alicyclic group, preferably a bulky group that suitably may contain 7 to about 20 carbons, such as an alkyladamantyl, ethylfencyl, tricyclo decanyl, or pinanyl group. Polymers of the invention are useful as a component of chemically-amplified positive-acting resists.
    Type: Grant
    Filed: December 6, 2002
    Date of Patent: April 20, 2010
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: George G. Barclay, Ashish Pandya, Wang Yueh, Anthony Zampini, Gary Ganghui Teng, Zhibiao Mao
  • Patent number: 7700261
    Abstract: A positive photosensitive composition comprises: (A) a compound that generates an acid upon irradiation with actinic ray or radiation; and (B) a resin that increases its solubility in an alkali developer by action of an acid, wherein the resin (B) has a repeating unit that has an acid-decomposable group and is represented by formula (I): wherein Xa1 represents a hydrogen atom, an alkyl group, a cyano group, or a halogen atom; Ry1 and Ry2 each independently represents an alkyl group or a cycloalkyl group; Rx represents an alkyl group having 2 or more carbon atoms, or a cycloalkyl group; and Z represents an alkylene group.
    Type: Grant
    Filed: March 26, 2008
    Date of Patent: April 20, 2010
    Assignee: FUJIFILM Corporation
    Inventors: Kunihiko Kodama, Kaoru Iwato, Hideaki Tsubaki, Norihiko Taguchi
  • Patent number: 7695892
    Abstract: A resist composition comprises (A) at least two kinds of resins each of which decomposes by the action of an acid to undergo an increase in its solubility for an alkali developer, wherein at least one kind of the resins (A) is a resin synthesized by living radical polymerization using a chain transfer agent represented by formula (I): wherein: A represents an organic group not containing hetero atoms; and Y represents an organic group capable of releasing a radical.
    Type: Grant
    Filed: March 24, 2008
    Date of Patent: April 13, 2010
    Assignee: FUJIFILM Corporation
    Inventors: Sou Kamimura, Yushi Kaneko
  • Patent number: 7691561
    Abstract: In a positive resist composition comprising (A) a resin component which becomes soluble in an alkaline developer under the action of an acid and (B) a photoacid generator, component (A) is a polymer of formula (1) wherein R1 is H, methyl or trifluoromethyl, R2 and R3 are alkyl, R4 is a monovalent hydrocarbon group, X1 is O, S or CH2CH2, X2 is O, S, CH2 or CH2CH2, n is 1 or 2, a and b each are from 0.01 to less than 1, c, d1 and d2 each are from 0 to less than 1, and a+b+c+d1+d2=1. The resist composition forms a pattern with high rectangularity at an enhanced resolution when processed by ArF lithography.
    Type: Grant
    Filed: July 5, 2007
    Date of Patent: April 6, 2010
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Ryosuke Taniguchi, Tsunehiro Nishi, Tomohiro Kobayashi
  • Patent number: 7687219
    Abstract: A positive resist composition comprises: (A) a resin that contains a repeating unit (A1) having a lactone structure and a cyano group, and increases its solubility to an alkali developer by action of an acid; (B) a compound that generates an acid by irradiation with actinic ray or radiation; and (C) a solvent.
    Type: Grant
    Filed: November 8, 2006
    Date of Patent: March 30, 2010
    Assignee: FUJIFILM Corporation
    Inventors: Kaoru Iwato, Kunihiko Kodama
  • Patent number: 7687221
    Abstract: Disclosed is a positive resist composition which can provide a positive resist composition and a resist pattern forming method, capable of forming a high resolution pattern with reduce LER, the positive resist composition comprising a resin component (A) which has acid dissociable, dissolution inhibiting groups and exhibits increased alkali solubility under the action of an acid, and an acid generator component (B) which generates an acid under exposure, wherein the resin component (A) contains a polymer compound (A1) having a structural unit (a1) derived from hydroxystyrene and a structural unit (a2) derived from an acrylate ester having acid dissociable, dissolution inhibiting groups, a fluorine atom or a fluorinated lower alkyl group being bonded at the ?-position.
    Type: Grant
    Filed: December 14, 2005
    Date of Patent: March 30, 2010
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Taako Hirosaki, Tomoyuki Ando, Takuma Hojo
  • Patent number: 7687223
    Abstract: There is provided an underlayer coating forming composition for lithography for forming an underlayer coating having a high dry etching rate compared with photoresist, causing no intermixing with the photoresist, and excellent in property of filling hole on the semiconductor substrate, which is used in lithography process of manufacture of semiconductor device. The composition comprises a cyclodextrin compound that 10% to 90% of total number of hydroxy groups in cyclodextrin is converted into an ether or ester group, a crosslinking compound, a crosslinking catalyst and a solvent.
    Type: Grant
    Filed: October 25, 2005
    Date of Patent: March 30, 2010
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Satoshi Takei, Tetsuya Shinjo, Keisuke Hashimoto
  • Patent number: 7682772
    Abstract: A compound represented by general formula (I); and a compound represented by general formula (b1-1). [Chemical Formula 1] X-Q1-Y1—SO3?M+??(I) X-Q1-Y1—SO3?A+??(b1-1) wherein Q1 represents a divalent linkage 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; X represents a cyclic group of 3 to 30 carbon atoms which may have a substituent, and has an —SO2— bond in the structure thereof; M+ represents an alkali metal ion; and A+ represents an organic cation.
    Type: Grant
    Filed: November 5, 2008
    Date of Patent: March 23, 2010
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Takehiro Seshimo, Yoshiyuki Utsumi, Akiya Kawaue, Hideo Hada, Hiroaki Shimizu, Tsuyoshi Nakamura
  • Patent number: 7678530
    Abstract: Lactone-containing compounds having formula (1) are novel wherein A1 is a polymerizable functional group having a double bond, R1 is a monovalent C1-C10 hydrocarbon group in which some or all hydrogen atoms are substituted by fluorine atoms, and W is CH2, O or S. They are useful as monomers to produce polymers for the formulation of radiation-sensitive resist compositions which have high transparency to radiation of up to 500 nm and exhibit good development properties. Radiation-sensitive resist compositions comprising the polymers as base resin exhibit high resolution and prevent dissolution in water and penetration of water when processed by immersion lithography.
    Type: Grant
    Filed: January 4, 2007
    Date of Patent: March 16, 2010
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Koji Hasegawa, Satoshi Watanabe, Jun Hatakeyama, Takeshi Kinsho, Seiichiro Tachibana
  • Patent number: 7670752
    Abstract: A photosensitive resin composition which is excellent in storage stability required for one-part type compositions and in processability required for dry-film formation and gives a cured product suitable for FPC substrates or suspension substrates for hard-disc which each retains essential properties required for solder resists, such as heat resistance, water resistance, and electrical-insulation reliability, and has flexibility and low polluting property. The composition comprises: a compound which has a carbon-carbon double bond and carboxy group and is obtained by allowing a bisphenol type epoxy compound and an unsaturated monocarboxylic acid to react and then allowing a polybasic acid anhydride to undergo addition reaction with part or all of the secondary hydroxy groups of the reaction product; a urethane (meth)acrylate compound having a structure derived from a polycarbonate polyol structure; another polymerizable compound having a carbon-carbon double bond; and a photopolymerization initiator.
    Type: Grant
    Filed: July 27, 2006
    Date of Patent: March 2, 2010
    Assignee: Toagosei Co., Ltd.
    Inventors: Makoto Hirakawa, Masao Takei, Hiroshi Niizuma
  • Patent number: 7670746
    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: July 22, 2004
    Date of Patent: March 2, 2010
    Assignee: FUJIFILM Corporation
    Inventor: Kunihiko Kodama
  • Patent number: 7666569
    Abstract: A positive resist composition including a resin component (A) containing an acid dissociable dissolution inhibiting group whose alkali solubility increases under action of acid and an acid generator component (B) that generates acid on exposure, wherein the resin component (A) is a copolymer comprising a first structural unit (a1) derived from a hydroxystyrene and a second structural unit (a2) derived from a (meth)acrylate ester containing an alcoholic hydroxyl group, in which 10 mol % or more and 25 mol % or less of a combined total of hydroxyl groups within the structural units (a1) and alcoholic hydroxyl groups within the structural units (a2) are protected with the acid dissociable dissolution inhibiting groups, and a weight average molecular weight of the copolymer prior to protection with the acid dissociable dissolution inhibiting groups is 2,000 or more and 8,500 or less.
    Type: Grant
    Filed: December 18, 2003
    Date of Patent: February 23, 2010
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Kazufumi Sato, Mitsuo Hagihara, Daisuke Kawana
  • Patent number: 7666574
    Abstract: A positive photosensitive composition comprises (A) a resin that has an acid decomposable repeating unit represented by formula (I) and increases its solubility in an alkali developer by action of an acid; (B) a compound generating an acid in irradiation with actinic light or radiation; (C) a resin that contains neither fluorine nor silicon and has a repeating unit having the predetermined structure; and (D) a solvent, wherein each symbol represents a predetermined group.
    Type: Grant
    Filed: March 28, 2008
    Date of Patent: February 23, 2010
    Assignee: FUJIFILM Corporation
    Inventors: Toshiaki Fukuhara, Shinichi Kanna, Hiromi Kanda
  • Patent number: 7662541
    Abstract: A photosensitive resin composition and a photosensitive dry film which are excellent in both sensitivity and stability and are well-balanced in tent strength, resolution and plating non-staining are provided. The photosensitive resin composition comprises an alkali-soluble resin (A), a photopolymerizable compound (B) and a photopolymerization initiator (C), and the polymerization initiator (C) comprises a hexaarylbisimidazole based compound (C1) and a multifunctional thiol compound (C2) as essential components. The photosensitive dry film has at least a photosensitive resin layer formed from the photosensitive resin composition on a support film.
    Type: Grant
    Filed: November 22, 2005
    Date of Patent: February 16, 2010
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Teruhiro Uematsu, Naoya Katsumata
  • Patent number: 7651830
    Abstract: Provided is an article that comprises a substrate comprising an acid-etchable layer, a water-soluble polymer matrix, and a photoacid generator. Also provided is a method for patterning that can provide patterned layers that can be used to form electroactive devices.
    Type: Grant
    Filed: June 1, 2007
    Date of Patent: January 26, 2010
    Assignee: 3M Innovative Properties Company
    Inventors: Wayne S Mahoney, Steven D. Theiss
  • Patent number: 7651831
    Abstract: A positive photoresist composition comprises a radiation sensitive acid generator, and a polymer that includes a first repeating unit derived from a sulfonamide monomer including a fluorosulfonamide functionality, a second repeating unit having a pendant acid-labile moiety, and a third repeating unit having a lactone functionality. The positive photoresist composition may be used to form patterned features on a substrate, such as those used in the manufacture of a semiconductor device.
    Type: Grant
    Filed: June 10, 2008
    Date of Patent: January 26, 2010
    Assignee: International Business Machines Corporation
    Inventors: Wenjie Li, Pushkara Rao Varanasi
  • Patent number: 7645563
    Abstract: The present invention is to obtain without any trouble a photosensitive resin composition, a photosensitive layer and a photosensitive resin printing original plate, which are developable with an aqueous developer, resistant to an aqueous ink and a cosolvent ink, and assured of good image reproducibility. The present invention relates to a photosensitive resin composition comprising (A) hydrophobic polymers obtained from at least two or more water dispersion latexes, (B) a photopolymerizable compound and (C) a photopolymerization initiator, wherein the two or more hydrophobic polymers each is present in a fine particle state.
    Type: Grant
    Filed: April 7, 2004
    Date of Patent: January 12, 2010
    Assignee: Toyo Boseki Kabushiki Kaisha
    Inventors: Toru Wada, Tomonori Hiramatsu, Akira Tomita
  • Patent number: 7645559
    Abstract: A positive resist composition and method of forming a resist pattern are provided which enable formation of a resist pattern having excellent shape with reduced LWR. The positive resist composition includes a resin component (A) which exhibits increased alkali solubility under action of acid and an acid-generator component (B) which generates acid upon irradiation, the resin component (A) having a structural unit (a1) which has an acetal-type protection group, and the acid-generator component (B) including an acid generator (B1) having a cation moiety represented by general formula (b-5) shown below: wherein Ra and Rb each independently represents an alkyl group, an alkoxy group, a halogen atom or a hydroxyl group; Rc represents an aryl group or alkyl group which may or may not have a substituent; and n? and n? each independently represents an integer of 0 to 3.
    Type: Grant
    Filed: August 16, 2006
    Date of Patent: January 12, 2010
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Ryoji Watanabe, Masaru Takeshita
  • Patent number: 7638257
    Abstract: A positive resist composition that includes a resin component (A) and an acid generator component (B), wherein the component (A) includes a polymer compound (A1) having a structural unit (a0) represented by a general formula (a0) shown below, and a structural unit (a1), which is derived from an (?-lower alkyl) acrylate ester containing an acid-dissociable, dissolution-inhibiting group and is not classified as the structural unit (a0): (wherein, R represents a hydrogen atom or a lower alkyl group; Y1 represents an aliphatic cyclic group; Z represents an alkoxyalkyl group; a represents an integer from 1 to 3, and b represents either 0 or an integer from 1 to 2, provided that a+b=1 to 3).
    Type: Grant
    Filed: October 4, 2005
    Date of Patent: December 29, 2009
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventor: Ryotaro Hayashi
  • Patent number: 7638264
    Abstract: A positive photoresist composition comprises a radiation sensitive acid generator, and a polymer that includes a first repeating unit derived from a sulfonamide monomer including a fluorosulfonamide functionality, a second repeating unit having a pendant acid-labile moiety, and a third repeating unit having a lactone functionality. The positive photoresist composition may be used to form patterned features on a substrate, such as those used in the manufacture of a semiconductor device.
    Type: Grant
    Filed: May 23, 2006
    Date of Patent: December 29, 2009
    Assignee: International Business Machines Corporation
    Inventors: Wenjie Li, Pushkara Rao Varanasi
  • Patent number: 7638260
    Abstract: A positive resist composition comprises (A) a resin component which becomes soluble in an alkaline developer under the action of an acid and (B) an acid generator. The resin (A) is a polymer comprising specific recurring units. When processed by ArF lithography, the composition is improved in resolution and forms a pattern with a minimal line edge roughness.
    Type: Grant
    Filed: November 29, 2007
    Date of Patent: December 29, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Akihiro Seki, Shigeo Tanaka, Katsuya Takemura, Tsunehiro Nishi
  • Patent number: 7638258
    Abstract: A positive resist composition includes a resin component (A) that exhibits increased alkali solubility under the action of acid, and an acid generator component (B) that generates acid upon exposure, wherein the resin component (A) is a mixture of a copolymer (A1) that includes a structural unit (a1) derived from an acrylate ester that contains an acid-dissociable, dissolution-inhibiting group, a structural unit (a2) derived from a methacrylate ester that contains a lactone-containing monocyclic group, and a structural unit (a3) derived from an acrylate ester that contains a polar group-containing polycyclic group, and a copolymer (A2) that has a different structure from the copolymer (A1) and has a lower hydrophilicity than the copolymer (A1).
    Type: Grant
    Filed: January 25, 2006
    Date of Patent: December 29, 2009
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventor: Masaru Takeshita
  • Patent number: 7635554
    Abstract: A positive photosensitive composition comprises: (A) a resin that has an acid decomposable repeating unit represented by formula (I) and increases its solubility in an alkali developer by action of an acid: (B) a compound generating an acid upon irradiation with actinic light or radiation; (C) a hydrophobic resin insoluble in an alkali developer and having at least either one of a fluorine atom and a silicon atom; and (D) a solvent, wherein in the formula (I), Xa1 represents a hydrogen atom, an alkyl group, a cyano group or a halogen atom, Ry1 to Ry3 each independently represents an alkyl group or a cycloalkyl group, and at least two of Ry1 to Ry3 may be coupled to form a ring structure, and Z represents a divalent linking group.
    Type: Grant
    Filed: March 28, 2008
    Date of Patent: December 22, 2009
    Assignee: FUJIFILM Corporation
    Inventors: Toshiaki Fukuhara, Shinichi Kanna, Hiromi Kanda
  • Patent number: 7632623
    Abstract: A positive resist composition comprising: a resin which increases solubility in an alkali developing solution by an action of an acid and comprises a repeating unit containing a lactone structure and a cyano group, a repeating unit containing a first group selected from groups represented by the formulae (pI) to (pV) as defined herein and a repeating unit containing a second group selected from groups represented by the formulae (pI) to (pV) as defined herein which is different from the first group; a compound which generates an acid upon irradiation of an actinic ray or a radiation; and a solvent.
    Type: Grant
    Filed: March 13, 2007
    Date of Patent: December 15, 2009
    Assignee: FUJIFILM Corporation
    Inventors: Kaoru Iwato, Kunihiko Kodama, Yuko Yoshida, Kei Yamamoto
  • Patent number: 7629106
    Abstract: There is disclosed a resist composition which shows high sensitivity and high resolution on exposure to high energy beam, provides reduced Line Edge Roughness because swelling at the time of development is reduced, provides minor amounts of residue after development, has excellent dry etching resistance, and can also be used suitably for the liquid immersion lithography; and a patterning process using the resist composition. There can be provided a resist composition which comprises, at least, a polymer including repeating units represented by the following general formulae (a) and (b).
    Type: Grant
    Filed: October 16, 2006
    Date of Patent: December 8, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Koji Hasegawa, Youichi Ohsawa, Seiichiro Tachibana
  • Patent number: 7629107
    Abstract: A positive photosensitive composition comprises: a polymer compound having an acid-decomposable structure on a terminal of the polymer compound; and a compound capable of generating an acid upon irradiation with actinic ray or radiation.
    Type: Grant
    Filed: September 18, 2007
    Date of Patent: December 8, 2009
    Assignee: FUJIFILM Corporation
    Inventors: Akinori Shibuya, Takayuki Kato
  • Patent number: 7629105
    Abstract: A positive resist composition that includes a resin component (A), which contains acid dissociable, dissolution inhibiting groups and exhibits increased alkali solubility under the action of acid, and an acid generator component (B) that generates acid on exposure, wherein the resin component (A) is a copolymer (A1) containing a first structural unit (a1) derived from hydroxystyrene and a second structural unit (a2) derived from a (meth)acrylate ester having an alcoholic hydroxyl group, in which a portion of the hydroxyl groups of the structural units (a1) and the alcoholic hydroxyl groups of the structural units (a2) have been protected with the acid dissociable, dissolution inhibiting groups; and either the acid generator component (B) includes a diazomethane-based acid generator and an onium salt-based acid generator; or the composition further contains a compound, which contains at least one acid dissociable, dissolution inhibiting group, and generates an organic carboxylic acid under the action of acid g
    Type: Grant
    Filed: September 17, 2004
    Date of Patent: December 8, 2009
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Akiyoshi Yamazaki, Kazuo Tani, Naoto Motoike, Satoshi Maemori, Sachiko Yoshizawa
  • Patent number: 7625690
    Abstract: A resist composition, which comprises: (A) a resin containing a repeating unit represented by formula (I); and (B) a compound capable of generating an acid upon irradiation with actinic rays or radiation: wherein AR represents an aryl group; Rn represents an alkyl group, a cycloalkyl group or an aryl group; and A represents an atom or group selected from the group consisting of a hydrogen atom, an alkyl group, a halogen atom, a cyano group and an alkyloxycarbonyl group, and a pattern forming method using the resist composition.
    Type: Grant
    Filed: March 14, 2007
    Date of Patent: December 1, 2009
    Assignee: FUJIFILM Corporation
    Inventors: Kazuyoshi Mizutani, Kaoru Iwato, Kunihiko Kodama, Masaomi Makino, Toru Tsuchihashi
  • Patent number: 7622242
    Abstract: A resist composition comprises a base polymer which changes its alkali solubility under the action of an acid, and an additive copolymer comprising recurring units (a) and (b). R1 is F or CF3, R2 and R3 are H or alkyl or form a ring, R4 is H or an acid labile group, R5 to R6 are H, F, or alkyl, or two of R5 to R8 may together form a ring, m=0 or 1, 0.2?a?0.8, and 0.1?b?0.6. A resist film of the composition has good barrier property against water so that leaching of the resist film with water is controlled, minimizing a change of pattern profile due to leach-out.
    Type: Grant
    Filed: September 23, 2008
    Date of Patent: November 24, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Koji Hasegawa, Takeru Watanabe, Yuji Harada
  • Patent number: 7618765
    Abstract: A positive resist composition comprises (A) a resin component which becomes soluble in an alkaline developer under the action of an acid, and (B) an acid generator which is a specific sulfonium salt compound. The resin (A) is a polymer comprising tertiary alkyl protective group units having a hydrophobic tetracyclo[4.4.0.12,5.17,10]dodecane structure, di- or trihydroxyadamantyl units, and monocyclic lactone units.
    Type: Grant
    Filed: January 2, 2008
    Date of Patent: November 17, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Tsunehiro Nishi, Seiichiro Tachibana, Katsuhiro Kobayashi
  • Patent number: 7618764
    Abstract: A positive resist composition comprises (A) a resin component which becomes soluble in an alkaline developer under the action of an acid and (B) an acid generator. The resin (A) is a polymer comprising specific recurring units. The acid generator (B) is a specific sulfonium salt compound. When processed by lithography, the composition is improved in resolution, and forms a pattern with a minimal line edge roughness.
    Type: Grant
    Filed: November 20, 2007
    Date of Patent: November 17, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Shigeo Tanaka, Akihiro Seki, Katsuya Takemura, Tsunehiro Nishi
  • Patent number: 7611822
    Abstract: The present invention provides a salt represented by the formula (I): wherein Q1 and Q2 each independently represent a fluorine atom or a C1-C6 perfluoroalkyl group, T represents a methylene group or a carbonyl group, R represents an adamantyl group substituted with at least one selected from the group consisting of a C1-C4 alkyl group, a C1-C4 alkoxy group, a hydroxyl group, a hydroxymethyl group, a cyano group and an oxo group, and A+ represents an organic counter ion. The present invention further provides a chemically amplified resist composition comprising the salt represented by the above-mentioned formula (I).
    Type: Grant
    Filed: July 22, 2008
    Date of Patent: November 3, 2009
    Assignee: Sumitomo Chemical Company, Limited
    Inventor: Ichiki Takemoto
  • Patent number: 7608389
    Abstract: Novel photoresist materials, which can be photolithographically processed in biocompatible conditions are presented in this invention. Suitable lithographic scheme for the use of these and analogous resists for biomolecule layer patterning on solid substrates are also described. The processes described enable micropatterning of more than two different proteins on solid substrates without denaturation of the proteins. The preferred resist materials are based on (meth)acrylate copolymers that contain at least one acid cleavable ester group and at least one hydrophilic group such as an alcoholic or a carboxylic group.
    Type: Grant
    Filed: May 30, 2002
    Date of Patent: October 27, 2009
    Assignees: National Centre for Scientific Research Demokritos
    Inventors: Panagiotis Argitis, Konstantinos Misiakos, Sotirios E. Kakabakos, Constantinos D. Diakoumakos
  • Patent number: 7608381
    Abstract: The positive resist composition of the present invention is a polymer compound comprising at least one constituent unit (a1) selected from the group consisting of constituent units represented by the following general formulas (1) and (1)?, a constituent unit (a2) derived from an (?-lower alkyl)acrylate ester having a lactone-containing monocycle or a polycyclic group, and a constituent unit (a3) which is a constituent unit other than the constituent unit (a1) and the constituent unit (a2) and is derived from an (?-lower alkyl)acrylate ester which has an aliphatic cyclic group-containing non-acid dissociable dissolution inhibiting group and does not have a polar group: wherein R represents a hydrogen atom, a fluorine atom, a lower alkyl group having 20 or less carbon atoms, or a fluorinated lower alkyl group having 20 or less carbon atoms, R1 represents at most 20-membered cyclic group which may have a substituent, n represents 0 or an integer of 1 to 5, and m represents 0 or 1.
    Type: Grant
    Filed: June 10, 2005
    Date of Patent: October 27, 2009
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Yohei Kinoshita, Takeshi Iwai
  • Patent number: 7604919
    Abstract: The photoresist monomer including an oxime group, a polymer thereof and a photoresist composition containing the same are disclosed. The photoresist monomer is represented by following Formula. In Formula, R* is independently a hydrogen or a methyl group, and R is a substituted or unsubstituted C1˜C25 alkyl group with or without an ether group, or a substituted or unsubstituted C4˜C25 hydrocarbon group including an aryl group, a heteroaryl group, a cycloalkyl group or a multicycloalkyl group with or without an ether group, a ketone group or a sulfur.
    Type: Grant
    Filed: September 10, 2007
    Date of Patent: October 20, 2009
    Assignee: Dongjin Semichem Co., Ltd.
    Inventors: Deog-Bae Kim, Jung-Youl Lee, Geun-Jong Yu, Sang-Jung Kim, Jae-Woo Lee, Jae-Hyun Kim
  • Patent number: 7604920
    Abstract: A compound represented by general formula (I) shown below; and a polymeric compound having a structural unit (a0) represented by general formula (a0-1) shown below: wherein R1 represents a hydrogen atom, a lower alkyl group or a halogenated lower alkyl group; A represents a divalent hydrocarbon group of 2 or more carbon atoms which may have a substituent; B represents a divalent hydrocarbon group of 1 or more carbon atoms which may have a substituent; and R2 represents an acid dissociable, dissolution inhibiting group.
    Type: Grant
    Filed: August 5, 2008
    Date of Patent: October 20, 2009
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Daiju Shiono, Takahiro Dazai, Hiroaki Shimizu
  • Patent number: 7601479
    Abstract: A polymer comprising recurring units of formulae (1) to (4) wherein R1, R3, R4 and R7 are hydrogen or methyl, R2 is an acid labile group, R5 and R6 are hydrogen or hydroxyl, and R8 is a lactone structure group and having a Mw of 1,000-50,000 is provided. A resist composition comprising the inventive polymer has a sensitivity to high-energy radiation, improved resolution and etching resistance and lends itself to lithographic micropatterning with electron beams or deep UV.
    Type: Grant
    Filed: September 9, 2004
    Date of Patent: October 13, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Seiichiro Tachibana, Tsunehiro Nishi, Tomohiro Kobayashi
  • Patent number: 7601482
    Abstract: The present invention relates to a negative photoresist composition comprising, a) at least one alkali-soluble polymer, where the polymer comprises at least one unit of structure 1, where, R? is selected independently from hydrogen, (C1-C4)alkyl, chlorine, bromine and m is an integer from 1 to 4; b) at least one monomer of structure 1, where, W is a multivalent linking group, R1 to R6 are independently selected from hydrogen, hydroxyl, (C1-C20) alkyl and chlorine, X1 and X2 are independently oxygen or N—R7, where R7 is hydrogen or (C1-C20) alkyl, and n is and integer equal to or greater than 1, and c) at least one photoinitiator. The invention also relates to a process for imaging the negative photoresist composition.
    Type: Grant
    Filed: March 28, 2006
    Date of Patent: October 13, 2009
    Assignee: AZ Electronic Materials USA Corp.
    Inventors: Georg Pawlowski, Chunwei Chen, Joseph Oberlander, Robert Plass
  • Patent number: RE41128
    Abstract: New polymers and new anti-reflective compositions containing such polymers are provided. The compositions comprise a polymer (e.g., epoxy cresol novolac resins) bonded with a chromophore (4-hydroxybenzoic acid, trimellitic anhydride). The inventive compositions can be applied to substrates (e.g., silicon wafers) to form anti-reflective coating layers having high etch rates which minimize or prevent reflection during subsequent photoresist exposure and developing.
    Type: Grant
    Filed: January 25, 2007
    Date of Patent: February 16, 2010
    Assignee: Brewer Science Inc.
    Inventor: Shreeram V. Deshpande