Polyolefin Or Halogen Containing Patents (Class 430/907)
  • Patent number: 7794914
    Abstract: The present invention provides a chemically amplified resist composition comprising: a resin (A) which contains no fluorine atom and a structural unit (a1) having an acid-labile group, a resin (B) which contains a structural unit (b2) having a fluorine-containing group and at least one structural unit selected from a structural unit (b1) having an acid-labile group, a structural unit (b3) having a hydroxyl group and a structural unit (b4) having a lactone structure, and an acid generator.
    Type: Grant
    Filed: February 12, 2007
    Date of Patent: September 14, 2010
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Nobuo Ando, Yusuke Fuji, Ichiki Takemoto
  • Patent number: 7771912
    Abstract: A positive resist composition comprises: (A) a resin of which solubility in an alkali developer increases under the action of an acid, (B) a compound capable of generating an acid upon irradiation with actinic rays or radiation, (C) a resin having at least one repeating unit selected from fluorine atom-containing repeating units represented by the following formulae (1-1), (1-2) and (1-3), the resin being stable to an acid and insoluble in an alkali developer, and (D) a solvent: wherein R1 represents a hydrogen atom or an alkyl group; R2 represents a fluoroalkyl group; R3 represents a hydrogen atom or a monovalent organic group; R4 to R7 each independently represents a hydrogen atom, a fluorine atom, an alkyl group, a fluoroalkyl group, an alkoxy group or a fluoroalkoxy group, provided that at least one of R4 to R7 represents a fluorine atom, and R4 and R5, or R6 and R7 may combine to form a ring; R8 represents a hydrogen atom, a fluorine atom or a monovalent organic group; Rf represents a fluorine atom
    Type: Grant
    Filed: December 11, 2006
    Date of Patent: August 10, 2010
    Assignee: FUJIFILM Corporation
    Inventors: Kei Yamamoto, Shinichi Kanna, Hiromi Kanda
  • Patent number: 7771913
    Abstract: There is disclosed a resist composition comprising, at least, a polymer including repeating units represented by the following general formula (1). There can be provided a resist composition that has a good barrier property against water, prevents resist components from leaching to water, has high receding contact angle against water, does not require a protective film, has an excellent process applicability, suitable for the liquid immersion lithography and makes it possible to form micropatterns with high precision.
    Type: Grant
    Filed: March 30, 2007
    Date of Patent: August 10, 2010
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Tatsushi Kaneko, Jun Hatakeyama, Yuji Harada
  • Patent number: 7771914
    Abstract: A resist composition comprises a polymer comprising recurring units having formula (1) wherein R1, R4, R7, and R14 are H or methyl, R2, R3, R15, and R16 are H, alkyl or fluoroalkyl, R is F or H, R5 is alkylene, R6 is fluorinated alkyl, R8 is a single bond or alkylene, R10 and R11 are H, F, methyl or trifluoromethyl, R12 and R13 are a single bond, —O— or —CR18R19—, R9, R18, and R19 are H, F, methyl or trifluoromethyl, R17 is alkylene, X1, X2 and X3 are —C(?O)—O—, —O—, or —C(?O)—R20—C(?O)—O— wherein R20 is alkylene, 0?(a-1)<1, 0?(a-2)<1, 0?(a-3)<1, 0<(a-1)+(a-2)+(a-3)<1, 0<b<1, and 0<(a-1)+(a-2)+(a-3)+b?1.
    Type: Grant
    Filed: October 16, 2007
    Date of Patent: August 10, 2010
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Takao Yoshihara, Yuji Harada, Wataru Kusaki
  • Patent number: 7763412
    Abstract: A polymer, a positive resist composition, and a method for forming a resist pattern that are able to form a resist pattern with a high level of resolution and excellent etching resistance. The present invention uses a polymer that contains a structural unit (a1) represented by a general formula (a-1) shown below and a structural unit (a2) represented by a general formula (a-2) shown below, another polymer that contains the structural unit (a1) and a structural unit (a3) represented by a general formula (a-3) shown below, and another polymer that contains the structural unit (a1), the structural unit (a2), and the structural unit (a3).
    Type: Grant
    Filed: June 2, 2005
    Date of Patent: July 27, 2010
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Masaru Takeshita, Hideo Hada, Ryotaro Hayashi, Takeshi Iwai, Syogo Matsumaru, Satoshi Fujimura
  • 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: 7709178
    Abstract: New photoresists for use during the production of semiconductor and MEMS devices are provided. The primer layer preferably comprises a silane dissolved or dispersed in a solvent system. The photoresist layer includes a first polymer prepared from a styrene and an acrylonitrile, and a second polymer comprising epoxy-containing monomers (and preferably phenolic-containing monomers). The photoresist layer comprises a photoacid generator, and is preferably negative-acting.
    Type: Grant
    Filed: April 17, 2007
    Date of Patent: May 4, 2010
    Assignee: Brewer Science Inc.
    Inventors: Xing-Fu Zhong, Tony D. Flaim, Jyoti Malhotra
  • 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: 7700257
    Abstract: A photoresist composition containing a polymer (A) containing an alkali-soluble constituent unit (a1) containing an alicyclic group having both a fluorine atom or a fluorinated alkyl group (i) and an alcoholic hydroxyl group (ii), whose alkali-solubility is changeable by an action of an acid; an acid generator (B) which generates an acid by light irradiation; and a dissolution inhibitor (C) having a fluorine atom(s) and/or a nitrogen-containing compound (D) selected from a tertiary amine (d1) having a polar group, a tertiary alkylamine (d2) having 7 or more and 15 or less of carbon atoms or an ammonium salt (d3). The composition has a resist property capable of accomplishing line and space (1:1) of 90 nm or less in good shape as a pattern processing accuracy of a semiconductor integrated circuit by lithography.
    Type: Grant
    Filed: March 24, 2004
    Date of Patent: April 20, 2010
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Toshiyuki Ogata, Kotaro Endo, Hiromitsu Tsuji, Masaaki Yoshida
  • Patent number: 7695895
    Abstract: An alkali-developable photosensitive color composition containing a binder resin, a fluorine-containing copolymer, a photopolymerization initiator, a colorant, and a solvent. A photopolymerizable unsaturated compound is used as the binder resin. The photopolymerizable unsaturated compound is obtained by adding (B) an unsaturated monobasic acid to (A) a polyfunctional epoxy resin to form (C) an epoxy adduct and allowing the epoxy adduct (C) and (D) a polybasic acid anhydride to react with each other.
    Type: Grant
    Filed: July 19, 2006
    Date of Patent: April 13, 2010
    Assignees: Toppan Printing Co., Ltd., Adeka Corporation
    Inventors: Hiroyuki Miura, Kazushige Kitazawa, Hideyuki Yamada, Masahide Tsuzuki, Ryota Chiba
  • Patent number: 7695890
    Abstract: New photoresists for use during the production of semiconductor and MEMS devices are provided. The primer layer preferably comprises a silane dissolved or dispersed in a solvent system. The photoresist layer includes copolymers prepared from styrene, acrylonitrile, and epoxy-containing monomers. The photoresist layer comprises a photoacid generator, and is preferably negative-acting.
    Type: Grant
    Filed: September 6, 2006
    Date of Patent: April 13, 2010
    Assignee: Brewer Science Inc.
    Inventors: Xing-Fu Zhong, Jyoti K. Malhotra, Chenghong Li
  • Patent number: 7696292
    Abstract: The invention pertains to low polydispersity acrylic polymers useful for photoimaging and photoresist compositions, and to the photoimaging processes which use these compositions. The low polydispersity polymers of this invention are prepared using controlled radical polymerization (CRP) techniques, such as RAFT (reversible addition fragmentation chain transfer) polymerization.
    Type: Grant
    Filed: September 16, 2004
    Date of Patent: April 13, 2010
    Assignee: Commonwealth Scientific and Industrial Research Organisation
    Inventors: William Brown Farnham, Michael Fryd, Frank Leonard Schadt, III
  • 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: 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: 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: 7678529
    Abstract: A multilayer resist process comprises forming in sequence an undercoat film, an intermediate film, and a photoresist film on a patternable substrate, and effecting etching in multiple stages. A silicon-containing film forming composition is useful in forming the intermediate film serving as an etching mask, comprising a silicon-containing polymer obtained through hydrolytic condensation of at least one Si—Si bond-containing silane compound having formula: R(6-m)Si2Xm wherein R is a monovalent hydrocarbon group, X is alkoxy, alkanoyloxy or halogen, and m is 3 to 6. The composition allows the overlying photoresist film to be patterned to a satisfactory profile and has a high etching selectivity relative to organic materials.
    Type: Grant
    Filed: November 8, 2006
    Date of Patent: March 16, 2010
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Tsutomu Ogihara, Takeshi Asano, Motoaki Iwabuchi, Takafumi Ueda
  • 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: 7666572
    Abstract: There is disclosed a resist top coat composition, comprising at least a polymer that has an amino group or a sulfonamide group at a polymer end and that is represented by the following general formula (1); and a patterning process comprising: at least, a step of forming a photoresist film on a substrate; a step of forming a resist top coat on the photoresist film by using the resist top coat composition; a step of exposing the substrate; and a step of developing the substrate with a developer. There can be provided a resist top coat composition that makes it possible to provide more certainly rectangular and excellent resist patterns when a top coat is formed on a photoresist film; and a patterning process using such a composition.
    Type: Grant
    Filed: June 11, 2007
    Date of Patent: February 23, 2010
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Yuji Harada, Jun Hatakeyama
  • Patent number: 7655378
    Abstract: There is disclosed a negative resist composition comprising, at least, a polymer comprising a repeating unit of hydroxy vinylnaphthalene represented by the following general formula (1). There can be provided a negative resist composition, in particular, a chemically amplified negative resist composition that can exhibit higher resolution than conventional hydroxy styrene or novolac negative resist compositions, that provides excellent pattern profiles after being exposed and that exhibits excellent etching resistance; and a patterning process that uses the resist composition.
    Type: Grant
    Filed: June 12, 2007
    Date of Patent: February 2, 2010
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Takanobu Takeda
  • 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: 7638256
    Abstract: Silicon compounds having fluorinated hemiacetal structure are provided. Silicone resins having the same structure have an appropriate acidity to enable formation of a finer pattern by minimizing the pattern collapse by swelling, exhibit improved resistance to the etching used in the pattern transfer to an organic film, and are thus suited for use in resist compositions for the bilayer process.
    Type: Grant
    Filed: July 6, 2006
    Date of Patent: December 29, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takeshi Kinsho, Takeru Watanabe, Mutsuo Nakashima, Yoshitaka Hamada
  • 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: 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: 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: 7618763
    Abstract: A hydroxystyrene/indene/alkoxyisobutoxystyrene copolymer having Mw of 1,000-500,000 is formulated as a base resin to give a resist composition, typically chemically amplified positive resist composition. The composition exhibits a high resolution, a satisfactory resist pattern profile after development, and improved etch resistance and is thus suitable as a micropatterning material for the fabrication of VLSI.
    Type: Grant
    Filed: November 6, 2006
    Date of Patent: November 17, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takanobu Takeda, Osamu Watanabe, Daisuke Manba, Tsugio Kaneda
  • 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: 7615332
    Abstract: A photosensitive compound has two or more structural units, in a molecule, represented by the following general formula (1): wherein R1 to R5 are selected from the group consisting of hydrogen atom, halogen atom, alkyl group, alkoxy group, acetoxy group, phenyl group, naphthyl group, and alkyl group in which a part or all of hydrogen atoms are substituted with fluorine atom; and X is a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthylene group.
    Type: Grant
    Filed: January 28, 2008
    Date of Patent: November 10, 2009
    Assignee: Canon Kabushiki Kaisha
    Inventors: Toshiki Ito, Takako Yamaguchi
  • 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: 7608382
    Abstract: A photoresist composition encompassing a polymer having at least one polycyclic olefin repeat unit having a desired exo mole percent is provided, where the repeat unit is derived from a polycyclic olefin monomer having the desired exo mole percent. Such polymers having such repeat units having a desired exo mole percent offer control of differential dissolution rate and hence provide enhanced imaging properties. Exemplary monomers having a desired exo mole percent are also provided.
    Type: Grant
    Filed: October 31, 2007
    Date of Patent: October 27, 2009
    Assignees: Promerus LLC, International Business Machines Corporation
    Inventors: Larry F. Rhodes, Chun Chang, Leah J. Langsdorf, Howard A. Sidaway, Hiroshi Ito
  • Patent number: 7598017
    Abstract: A negative resist composition including: a fluorine-containing resin component (F) containing a structural unit (f1) represented by a general formula (f1-0) shown below, and a structural unit (f2) having an alkali-soluble group, an alkali-soluble resin component (A) excluding the fluorine-containing resin component (F), an acid generator component (B) that generates acid upon exposure, and a cross-linking component (C). [wherein, R7 represents a fluorinated alkyl group, and a represents either 0 or 1.
    Type: Grant
    Filed: October 24, 2008
    Date of Patent: October 6, 2009
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Jun Iwashita, Kazuhito Sasaki, Sho Abe
  • Patent number: 7598016
    Abstract: To a resist composition comprising a polymer which changes its alkali solubility under the action of an acid as a base resin, is added a copolymer comprising recurring units containing a carboxylic acid ammonium salt and recurring units containing at least one fluorine atom as an additive. The composition is suited for immersion lithography.
    Type: Grant
    Filed: March 21, 2008
    Date of Patent: October 6, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Tomohiro Kobayashi, Jun Hatakeyama, Yuji Harada
  • Patent number: 7592122
    Abstract: A high-molecular compound and a low-molecular compound or both having an alkali-soluble site (i) wherein at least a part of the alkali-soluble site (i) is protected with (ii) a halogen atom-containing acetal type acid-dissociative, dissolution inhibiting group, as well as a photoresist composition comprising the same. The photoresist composition is highly stable during storage and can give a resist pattern excellent in sectional rectangular shape and having high transparency to an exposure light, particularly a light having a wavelength of 300 nm or less.
    Type: Grant
    Filed: April 15, 2004
    Date of Patent: September 22, 2009
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Toshiyuki Ogata, Kotaro Endo, Hiromitsu Tsuji, Masaaki Yoshida, Mitsuru Sato, Syogo Matsumaru, Hideo Hada
  • Patent number: 7592126
    Abstract: A positive resist composition comprising: (A) a resin insoluble or sparingly soluble in an alkali but capable of decomposing under an action of an acid to increase a solubility in an alkali developer, the resin having a ?-(meth)acroyloxy-?-butyrolactone repeating unit represented by the following formula (1) containing a lactone ring which may have a substituent; and (B) a compound capable of generating an organic acid represented by the formula (2), (3), (3?), (4) or (5) as defined herein upon irradiation of actinic rays or radiation.
    Type: Grant
    Filed: March 17, 2006
    Date of Patent: September 22, 2009
    Assignee: FUJIFILM Corporation
    Inventor: Fumiyuki Nishiyama
  • Patent number: 7588876
    Abstract: A resist material includes a base polymer containing a compound having a unit represented by a general formula of the following Chemical Formula 1: wherein R1, R2 and R3 are the same or different and are a hydrogen atom, a fluorine atom, a straight-chain alkyl group, a branched or cyclic alkyl group or a fluoridated alkyl group with a carbon number not less than 1 and not more than 20; R4 is a straight-chain alkylene group or a branched or cyclic alkylene group with a carbon number not less than 0 and not more than 20; R5 is a hydrogen atom, a straight-chain alkyl group, a branched or cyclic alkyl group or a fluoridated alkyl group with a carbon number not less than 1 and not more than 20, or a protecting group released by an acid; and R6 is a group having a cyclic ester compound, a group having an alicyclic compound including a hydroxyl group or a group having a compound including hexafluoroisopropyl alcohol.
    Type: Grant
    Filed: May 13, 2005
    Date of Patent: September 15, 2009
    Assignee: Panasonic Corporation
    Inventors: Shinji Kishimura, Masayuki Endo, Masaru Sasago, Mitsuru Ueda, Hirokazu Imori, Toshiaki Fukuhara
  • Patent number: 7582409
    Abstract: A negative resist composition that includes an alkali-soluble resin component, an acid generator component that generates acid upon exposure, and a cross-linker component, wherein the alkali-soluble resin component is a copolymer that includes a structural unit containing an aliphatic cyclic group having a fluorinated hydroxyalkyl group, and a structural unit derived from an acrylate ester that contains a hydroxyl group-containing aliphatic cyclic group, and the cross-linker component includes an alkylene urea-based cross-linker.
    Type: Grant
    Filed: June 16, 2006
    Date of Patent: September 1, 2009
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Jun Iwashita, Ayako Kusaka
  • Patent number: 7579131
    Abstract: A positive resist composition comprising: (A) a fluorine atom-containing resin; (B) a compound generating an acid upon irradiation with an actinic ray; and (C) a non-polymer dissolution inhibitor having a specific structure.
    Type: Grant
    Filed: July 23, 2004
    Date of Patent: August 25, 2009
    Assignee: FUJIFILM Corporation
    Inventor: Tomoya Sasaki
  • Patent number: 7579132
    Abstract: The present invention provides a salt represented by the formula (I): wherein X represents an n-valent connecting group, Y1 and Y2 each independently represent a fluorine atom or a C1-C6 perfluoroalkyl group, n represents 2 or 3, 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: June 4, 2007
    Date of Patent: August 25, 2009
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yukako Harada, Isao Yoshida, Satoshi Yamaguchi
  • Patent number: 7569323
    Abstract: A resist protective coating material is provided comprising an ?-trifluoromethylacrylic acid/norbornene copolymer having cyclic perfluoroalkyl groups as pendant. In a pattern-forming process, the material forms on a resist film a protective coating which is water-insoluble, dissolvable in alkaline developer and immiscible with the resist film, allowing for effective implementation of immersion lithography.
    Type: Grant
    Filed: July 26, 2006
    Date of Patent: August 4, 2009
    Assignees: Shin-Etsu Chemical Co., Ltd., Panasonic Corporation, Central Glass Co., Ltd.
    Inventors: Jun Hatakeyama, Yuji Harada, Yoshio Kawai, Masayuki Endo, Masaru Sasago, Haruhiko Komoriya, Michitaka Ootani, Satoru Miyazawa, Kazuhiko Maeda
  • Patent number: 7569326
    Abstract: A sulfonium salt having a polymerizable anion generates a strong sulfonic acid upon exposure to high-energy radiation so that it facilitates effective scission of acid labile groups in chemically amplified resist compositions. It is useful as a monomer from which a base resin for use in radiation-sensitive resist compositions is derived.
    Type: Grant
    Filed: October 25, 2007
    Date of Patent: August 4, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Masaki Ohashi, Seiichiro Tachibana, Jun Hatakeyama, Takeru Watanabe
  • Patent number: 7550247
    Abstract: A resist composition is provided comprising a silicone resin, a photoacid generator, a nitrogen-containing organic compound, and a solvent. The silicone resin is obtained through cohydrolytic condensation of a mixture of three silane monomers containing an organic group having a hydroxyl group and having at least 3 fluorine atoms, in total, on a proximate carbon atom, an organic group having a carboxyl group protected with an acid labile group, and a lactone ring-bearing organic group, respectively. The resist composition has satisfactory resolution and overcomes the problem of a low selective etching ratio between resist film and organic film during oxygen reactive etching.
    Type: Grant
    Filed: August 18, 2005
    Date of Patent: June 23, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Mutsuo Nakashima, Yoshitaka Hamada, Katsuya Takemura, Kazumi Noda, Toshihiko Fujii
  • Patent number: 7537880
    Abstract: To a resist composition, an alkali-soluble polymer having fluorinated ester-containing lactone units incorporated therein is included as an additive. The resist composition forms a resist film having a reduced contact angle after development. The resist film prevents water penetration during immersion lithography.
    Type: Grant
    Filed: October 3, 2007
    Date of Patent: May 26, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Yuji Harada, Jun Hatakeyama, Takao Yoshihara, Wataru Kusaki, Tomohiro Kobayashi, Koji Hasegawa
  • Patent number: 7534548
    Abstract: A polymer for immersion lithography comprising a repeating unit represented by Formula 1 and a photoresist composition containing the same. A photoresist film formed by the photoresist composition of the invention is highly resistant to dissolution, a photoacid generator in an aqueous solution for immersion lithography, thereby preventing contamination of an exposure lens and deformation of the photoresist pattern by exposure.
    Type: Grant
    Filed: December 15, 2005
    Date of Patent: May 19, 2009
    Assignee: Hynix Semiconductor Inc.
    Inventors: Jae Chang Jung, Cheol Kyu Bok, Chang Moon Lim, Seung Chan Moon
  • Patent number: 7534549
    Abstract: A photoresist polymer comprising a fluorine component, a photoresist composition containing the photoresist polymer and an organic solvent to reduce surface tension, and a method for manufacturing a semiconductor device using the same by forming a photoresist film uniformly on the whole surface of an underlying layer pattern to allow a subsequent ion-implanting process to be performed stably.
    Type: Grant
    Filed: December 20, 2005
    Date of Patent: May 19, 2009
    Assignee: Hynix Semiconductor Inc.
    Inventor: Jae Chang Jung
  • Patent number: 7531286
    Abstract: 1. A radiation-sensitive resin composition comprising: (A) a resin insoluble or scarcely soluble in alkali, but becomes alkali soluble by the action of an acid and (B) a photoacid generator. The resin comprises (a) at least one recurring unit of the following formula (1-1) or (1-2), and (b) at least one recurring unit for the following formula (2-1), (2-2), or (2-3).
    Type: Grant
    Filed: March 13, 2003
    Date of Patent: May 12, 2009
    Assignee: JSR Corporation
    Inventors: Yukio Nishimura, Hiroyuki Ishii, Masafumi Yamamoto, Isao Nishimura
  • Patent number: 7531290
    Abstract: Sulfonate salts have the formula: R1SO3—CH(Rf)—CF2SO3?M+ wherein R1 is alkyl or aryl, Rf is H or trifluoromethyl, and M+ is a Li, Na, K, ammonium or tetramethylammonium ion. Onium salts, oximesulfonates and sulfonyloxyimides and other compounds derived from these sulfonate salts are effective photoacid generators in chemically amplified resist compositions.
    Type: Grant
    Filed: October 27, 2006
    Date of Patent: May 12, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Katsuhiro Kobayashi, Youichi Ohsawa, Takeshi Kinsho, Takeru Watanabe
  • Patent number: 7514204
    Abstract: A resist composition comprises a polymer which increases its alkali solubility under the action of an acid as a base resin, and a copolymer comprising recurring units containing a sulfonic acid amine salt and recurring units containing at least one fluorine atom as an additive. The composition is suited for immersion lithography.
    Type: Grant
    Filed: October 23, 2007
    Date of Patent: April 7, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Wataru Kusaki, Yuji Harada, Takao Yoshihara
  • Patent number: 7514197
    Abstract: The resist according to the present invention includes any one of tetrachloromethyl tetramethoxycalix [4] arene and trichloromethyl tetramethoxycalix [4] arene. The resist including such kind of components is soluble in the solvent having less effect to worsen a working environment, namely, ethyl lactate (EL), propylene glycol monomethyl ether (PGME), propylene glycol monomethyl ether acetate (PGMEA), ethyl propionate, n-butyl acetate and 2-heptanone. It can be developed by tetra-methyl ammonium hydroxide in addition to the above mentioned solvent. By exposing this resist by electronic ray, high resolution of 8 nm is attained, and by using this resist as a mask, various materials can be formed into a hyperfine shape. According to such kind of resist, a photosensitive resist material which has high resolution and solvable to solvents having less effect to worsen the working environment and can be developed by the solvents, a exposure method using it, and a hyperfine processing method using it are provided.
    Type: Grant
    Filed: September 4, 2003
    Date of Patent: April 7, 2009
    Assignees: NEC Corporation, Tokuyama Corporation
    Inventors: Yukinori Ochiai, Masahiko Ishida, Junichi Fujita, Takashi Ogura, Junji Momoda, Eiji Oshima