Polymer Of Unsaturated Acid Or Ester Patents (Class 430/910)
  • Patent number: 7485413
    Abstract: The photosensitive composition of the invention contains a polymer material having a group having a structure represented by following general formula (2), and a photo acid generator generating acid with an ultraviolet ray or an ionizing radiation wherein m represents an integer of 0 or more.
    Type: Grant
    Filed: May 22, 2007
    Date of Patent: February 3, 2009
    Assignee: Kabushiki Kaisha Toshiba
    Inventor: Satoshi Saito
  • Patent number: 7482111
    Abstract: It is an object of the present invention to provide a process capable of precisely producing a plated shaped article of a large thickness such as a bump or a wiring, a negative radiation-sensitive resin composition which is preferably used for the process and has excellent sensitivity and resolution, and a transfer film using the composition. The above object is achieved by a negative radiation-sensitive resin composition comprising (A) a polymer containing structural units represented by the following formula (1) and/or the following formula (2), (B) a compound having at least one ethylenically unsaturated double bond and (C) a radiation-sensitive radical polymerization initiator, and by forming a negative radiation-sensitive resin film using the composition.
    Type: Grant
    Filed: March 24, 2005
    Date of Patent: January 27, 2009
    Assignee: JSR Corporation
    Inventors: Kouji Nishikawa, Tooru Kimura, Shin-ichiro Iwanaga
  • Patent number: 7476492
    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: May 26, 2006
    Date of Patent: January 13, 2009
    Assignee: International Business Machines Corporation
    Inventors: Robert David Allen, Richard Anthony DiPietro, Ratnam Sooriyakumaran, Hoa D. Truong
  • Patent number: 7476488
    Abstract: The photosensitive composition of the invention contains a polymer material having a group having a structure represented by following general formula (2), and a photo acid generator generating acid with an ultraviolet ray or an ionizing radiation wherein m represents an integer of 0 or more.
    Type: Grant
    Filed: May 24, 2007
    Date of Patent: January 13, 2009
    Assignee: Kabushiki Kaisha Toshiba
    Inventor: Satoshi Saito
  • Patent number: 7459261
    Abstract: There is disclosed a resist composition which comprises, at least, a polymer in which a sulfonium salt having a polymerizable unsaturated bond, a (meth)acrylate having a lactone or a hydroxyl group as an adhesion group, and a (meth)acrylate having an ester substituted with an acid labile group are copolymerized. There can be provided a resist composition with high resolution which has high sensitivity and high resolution to high energy beam, especially to ArF excimer laser, F2 excimer laser, EUV, X-ray, EB, etc., has reduced line edge roughness, and comprises a polymeric acid generator which has insolubility in water, and sufficient thermal stability and preservation stability.
    Type: Grant
    Filed: December 19, 2005
    Date of Patent: December 2, 2008
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Youichi Ohsawa, Seiichiro Tachibana
  • Patent number: 7452638
    Abstract: A radiating-sensitive composition and negative-working imageable element includes a free radically polymerizable component, an initiator composition capable of generating radicals sufficient to initiate polymerization of the free radically polymerizable component upon exposure to imaging radiation, a radiation absorbing compound, and particles of a poly(urethane-acrylic) hybrid that are distributed throughout the composition forming an imageable layer in the element. Imaging can be accomplished at a wide range of wavelengths from about 150 to about 1500 nm, and development can be accomplished using an organic solvent-based developer, warm water, plate cleaner, or on-press using a combination of a lithographic printing ink and a fountain solution.
    Type: Grant
    Filed: September 18, 2006
    Date of Patent: November 18, 2008
    Assignee: Eastman Kodak Company
    Inventors: Jianfei Yu, Kevin B. Ray, Shashikant Saraiya, Thomas R. Jordan, Paul R. West
  • Patent number: 7449276
    Abstract: The invention provides a positive photoresist composition which exhibits a high level of etching resistance and attains high resolution, and enables the formation of a fine pattern using an electron beam exposure step, as well as a method for forming a resist pattern that uses the positive photoresist composition. This positive photoresist composition for use with EB contains a resin component (A) that exhibits increased alkali solubility under the action of acid, an acid generator component (B) that generates acid on exposure, and an organic solvent (C), wherein the component (A) comprises a copolymer 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, and a portion of the hydroxyl groups of the structural units (a1) and the alcoholic hydroxyl groups of the structural units (a2) are protected with acid dissociable, dissolution inhibiting groups.
    Type: Grant
    Filed: April 22, 2004
    Date of Patent: November 11, 2008
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Takuma Hojo, Kiyoshi Ishikawa, Tsuyoshi Nakamura, Tasuku Matsumiya
  • Patent number: 7442490
    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 and a repeating unit containing a first acid-decomposable group; 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 and a repeating unit containing a second acid-decomposable group which is different from the first acid-decomposable group; a compound which generates an acid upon irradiation of an actinic ray or a radiation; and a solvent.
    Type: Grant
    Filed: March 16, 2007
    Date of Patent: October 28, 2008
    Assignee: FUJIFILM Corporation
    Inventors: Kaoru Iwato, Kunihiko Kodama
  • Patent number: 7435530
    Abstract: A positive type resin composition comprising (A) a resin component comprising within the principal chain a structural unit derived from a (meth)acrylate ester and incorporating an acid dissociable, dissolution inhibiting group containing a polycyclic group on an ester side chain section, for which the solubility in alkali increases under the action of acid, (B) an acid generator component which generates acid on exposure, and (C) an organic solvent, wherein the component (A) comprises both a structural unit derived from a methacrylate ester and a structural unit derived from an acrylate ester. According to such a resist composition, a resist pattern can be formed which displays little surface roughness and line edge roughness on etching, and also offers excellent resolution and a wide depth of focus range.
    Type: Grant
    Filed: January 9, 2007
    Date of Patent: October 14, 2008
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Takeshi Iwai, Naotaka Kubota, Satoshi Fujimura, Miwa Miyairi, Hideo Hada
  • Patent number: 7432034
    Abstract: A negative resist composition of the present invention comprises: (A) an alkali-soluble resin; (B-1) a cross-linking agent capable of cross-linking with the alkali-soluble resin (A) by the action of an acid, in which the cross-linking agent is a phenol compound containing: in the molecule one or more benzene rings; and at least two cross-linking groups bonded to any of the benzene rings, the cross-linking group being a group selected from the group consisting of a hydroxymethyl group, an alkoxymethyl group and an acyloxymethyl group; (B-2) a cross-linking agent capable of cross-linking with the alkali-soluble resin (A) by the action of an acid, in which the cross-linking agent contains at least two specific groups; and (C) a compound capable of generating an acid upon irradiation with an actinic ray or radiation.
    Type: Grant
    Filed: August 18, 2003
    Date of Patent: October 7, 2008
    Assignee: FUJIFILM Corporation
    Inventors: Shoichiro Yasunami, Koji Shirakawa
  • Patent number: 7419769
    Abstract: A negative photoresist composition is used for the formation of thick films and includes (A) a novolak resin, (B) a plasticizer, (C) a crosslinking agent and (D) an acid generator. The composition is applied onto a substrate and thereby yields a photoresist film 5 to 100 ?m thick. Likewise, the composition is applied onto a substrate of an electronic part, is patterned, is plated and thereby yields a bump.
    Type: Grant
    Filed: October 26, 2005
    Date of Patent: September 2, 2008
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Koji Saito, Kouichi Misumi, Toshiki Okui, Hiroshi Komano
  • Patent number: 7419761
    Abstract: A photoresist polymer having a spiro cyclic ketal group, and a photoresist composition including the same is disclosed. The photoresist polymer and the photoresist composition can improve the resolution and the process margin due to its low activation energy of the deprotection reaction of the spiro cyclic ketal group, and can produce fine photoresist patterns due to its low PEB (Post Exposure Baking) temperature sensitivity.
    Type: Grant
    Filed: September 15, 2005
    Date of Patent: September 2, 2008
    Assignee: Dongjin Semichem Co., Ltd.
    Inventors: Jae-Woo Lee, Jung-Youl Lee, Deog-Bae Kim, Jae-Hyun Kim, Eun-Kyung Son
  • Patent number: 7419760
    Abstract: Disclosed herein is a top anti-reflective coating composition comprising a bissulfone compound, as a photoacid generator, represented by Formula 1 below: wherein R1 and R2 are independently, a straight, branched or cyclic alkyl, aryl, alkenyl, oxoalkyl or oxoaryl group of 1 to 20 carbon atoms; or a halogen-substituted straight, branched or cyclic alkyl, aryl, alkenyl, oxoalkyl or oxoaryl group of 1 to 20 carbon atoms. Since the top anti-reflective coating composition dissolves a portion of a photoacid generator present at the top of an underlying photosensitizer, particularly, upon formation of a top anti-reflective coating, it can prevent the top from being formed into a thick section. Therefore, the use of the anti-reflective coating composition enables the formation of a vertical pattern of a semiconductor device.
    Type: Grant
    Filed: June 22, 2005
    Date of Patent: September 2, 2008
    Assignee: Hynix Semiconductor Inc.
    Inventors: Jae Chang Jung, Cheol Kyu Bok, Sam Young Kim, Chang Moon Lim, Seung Chan Moon
  • Patent number: 7416821
    Abstract: Thermally curable undercoat composition comprising for producing a bilayer relief image comprising: a) a polymer of Structure I comprising repeating units of Structure II, III, and IV b) a phenolic crosslinker; c) a thermal acid generator (TAG); and d) a solvent.
    Type: Grant
    Filed: March 9, 2005
    Date of Patent: August 26, 2008
    Assignee: Fujifilm Electronic Materials, U.S.A., Inc.
    Inventors: Binod B De, Sanjay Malik, J. Thomas Kocab, Thomas Sarubbi
  • Patent number: 7413843
    Abstract: A base polymer of a resist material includes a unit represented by a general formula of the following Chemical Formula 3: 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; and R5 and R6 are the same or different and are a hydrogen atom, a straight-chain alkyl group, a branched or cyclic alkyl group, 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.
    Type: Grant
    Filed: December 20, 2006
    Date of Patent: August 19, 2008
    Assignee: Matsushita Electric Industrial Co., Ltd.
    Inventors: Shinji Kishimura, Masayuki Endo, Masaru Sasago, Mitsuru Ueda, Hirokazu Imori, Toshiaki Fukuhara
  • Patent number: 7407733
    Abstract: A polymeric compound of the invention includes at least one monomer unit represented by the following formula (I); wherein Ra is a hydrogen atom, a halogen atom, an alkyl group of 1 to 6 carbon atoms or an haloalkyl group of 1 to 6 carbon atoms; each of R1 and R2 is identical to or different from a hydrogen atom or a hydrocarbon group, provided that at least one of R1 and R2 is a hydrocarbon group; R1 and R2 may be bonded together to form a ring with an adjacent carbon atom; and each of R3, R4, R5, R6, R7, R8 and R9 is identical to or different from a hydrogen atom or a hydrocarbon group. This polymeric compound has not only high substrate adhesion and high etching resistance but also high solubility for a resist solvent.
    Type: Grant
    Filed: May 25, 2005
    Date of Patent: August 5, 2008
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Hiroshi Koyama, Takeshi Asada
  • Patent number: 7405028
    Abstract: A bottom antireflective coating for photolithography at 157 nm or less, where the bottom antireflective coating includes a crosslinkable polymer which contains cinnamic acid derivatives.
    Type: Grant
    Filed: January 28, 2005
    Date of Patent: July 29, 2008
    Assignee: Infineon Technologies, AG
    Inventor: Christoph Hohle
  • Patent number: 7402379
    Abstract: A resist exposure system and a method of forming a pattern on a resist are provided and include an exposure source, a photoresist composition, and a mask positioned therebetween. The resist composition comprises a first photoresist X and a second photoresist Y. The first photoresist X absorbs at a higher wavelength than the second photoresist Y. The second photoresist Y has a lower glass transitional temperature than the first photoresist X.
    Type: Grant
    Filed: February 23, 2006
    Date of Patent: July 22, 2008
    Assignee: Micron Technology, Inc.
    Inventor: Yoshiki Hishiro
  • Patent number: 7402372
    Abstract: A positive resist composition includes a resin (A) that increases alkali solubility due to action of an acid, wherein the resin comprises a copolymer containing a first structural unit (a1) derived from hydroxystyrene, and a second structural unit (a2) derived from a (meth)acrylate with an alcoholic hydroxyl group, and a weight average molecular weight of the copolymer is within a range from 2000 to 8500, and 10 mol % to 25 mol % of a combined total of hydroxyl groups within the structural units (a1) and alcoholic hydroxyl groups within the structural units (a2) are protected with acid dissociable, dissolution inhibiting groups, an acid generator (B) that generates an acid on exposure to light, and polypropylene glycol (C).
    Type: Grant
    Filed: June 10, 2004
    Date of Patent: July 22, 2008
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Mitsuo Hagihara, Taku Nakao, Kazuyuki Nitta
  • Patent number: 7390612
    Abstract: There is provided a positive type resin composition comprising (A) a resin component comprising within the principal chain a structural unit derived from a (meth)acrylate ester and incorporating an acid dissociable, dissolution inhibiting group containing a polycyclic group on an ester side chain section, for which the solubility in alkali increases under the action of acid, (B) an acid generator component which generates acid on exposure, and (C) an organic solvent, wherein the component (A) comprises both a structural unit derived from a methacrylate ester and a structural unit derived from an acrylate ester. According to such a resist composition, a resist pattern can be formed which displays little surface roughness and line edge roughness on etching, and also offers excellent resolution and a wide depth of focus range.
    Type: Grant
    Filed: February 2, 2006
    Date of Patent: June 24, 2008
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Takeshi Iwai, Naotaka Kubota, Satoshi Fujimura, Miwa Miyairi, Hideo Hada
  • Patent number: 7378218
    Abstract: A fluorinated polymer comprising recurring units of formulae (1a) to (1d) and having a Mw of 1,000-500,000 is provided. R1 is an acid labile group, R2 is a single bond or methylene, a1, a2, a3, and a4 are numbers from more than 0 to less than 1, and 0<a1+a2+a3+a4?1, b is 1 or 2, and c is 0 or 1.
    Type: Grant
    Filed: February 2, 2006
    Date of Patent: May 27, 2008
    Assignees: Shin-Etsu Chemical Co., Ltd., Matsushita Electric Industrial Co., Ltd., Central Glass Co., Ltd.
    Inventors: Yuji Harada, Jun Hatakeyama, Yoshio Kawai, Masaru Sasago, Masayuki Endo, Kazuhiko Maeda, Haruhiko Komoriya, Michitaka Ootani
  • Patent number: 7374860
    Abstract: The invention provides a positive resist composition for the pattern formation by the use of actinic rays or radiation, ensuring that the sensitivity, resolution and pattern profile are good, the line edge roughness is small and the surface roughness is satisfied, and a pattern forming method using the composition, wherein the positive resist composition is a positive resist composition comprising (A) a compound capable of generating an acid upon irradiation with actinic rays or radiation, and (B) a resin of which solubility in an alkali developer increases under the action of an acid, the resin comprising a specific repeating unit; and a pattern forming method using the composition.
    Type: Grant
    Filed: March 20, 2006
    Date of Patent: May 20, 2008
    Assignee: Fuji Film Corporation
    Inventors: Shuji Hirano, Kazuyoshi Mizutani
  • Patent number: 7371503
    Abstract: A sulfonium salt compound excelling in transparency to deep ultraviolet rays at a wavelength of 220 nm or less, exhibiting well-balanced excellent performance such as sensitivity, resolution, pattern form, LER, and storage stability when used as a photoacid generator, a photoacid generator comprising the sulfonium salt compound, and a positive-tone radiation-sensitive resin composition containing the photoacid generator. The sulfonium salt compound is shown by the following formula (I), wherein R1 represents a halogen atom, an alkyl group, a monovalent alicyclic hydrocarbon group, an alkoxyl group, or —OR3 group, wherein R3 is a monovalent alicyclic hydrocarbon group, R2 represents a (substituted)-alkyl group or two or more R2 groups form a cyclic structure, p is 0-7, q is 0-6, n is 0-3, and X? indicates a sulfonic acid anion. The positive-tone radiation-sensitive resin composition comprises (A) a photoacid generator of the sulfonium-salt compound and (B) an acid-dissociable group-containing resin.
    Type: Grant
    Filed: January 9, 2004
    Date of Patent: May 13, 2008
    Assignee: JSR Corporation
    Inventors: Takashi Miyamatsu, Hirokazu Niwata, Satoshi Ebata, Yong Wang
  • Patent number: 7371505
    Abstract: A positive working photosensitive composition which is useful in the manufacturing step of a semiconductor such as IC, the manufacture of a circuit board such as liquid crystals and thermal heads, and other fabrication steps and has an excellent resolution and line edge roughness, and a method for forming a pattern using the same, are provided, which are a photosensitive composition containing (A) a resin having a repeating unit having a specific group, whose solubility in an alkaline developer increases by the action of an acid, and a method for forming a pattern using the same.
    Type: Grant
    Filed: June 28, 2005
    Date of Patent: May 13, 2008
    Assignee: FUJIFILM Corporation
    Inventor: Kunihiko Kodama
  • Patent number: 7368218
    Abstract: A polymer which is obtained from a combination of (meth)acrylate having a bridged ring lactone group and (meth)acrylate having an acid leaving group with a hexafluoroalcohol group is used as a base resin to formulate a positive resist composition which when exposed to high-energy radiation and developed, exhibits a high sensitivity, a high resolution, and a minimal line edge roughness due to controlled swell during development. The composition also has excellent dry etching resistance.
    Type: Grant
    Filed: April 8, 2005
    Date of Patent: May 6, 2008
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Tatsushi Kaneko
  • Patent number: 7365115
    Abstract: An anti-reflective coating film is formed by applying on a chemically amplified photoresist film an anti-reflective coating composition comprising an alkali-soluble fluorine-containing polymer, an acid, an amine and a solvent capable of dissolving these components and having a pH of 7 or less. The formed anti-reflective coating film can serve to prevent multiple reflections within the photoresist film, increase the amount of reduction in thickness of the photoresist film upon development with a developer after exposure, and form a pattern having a rectangular cross-sectional pattern and not having T-top or round top.
    Type: Grant
    Filed: June 26, 2003
    Date of Patent: April 29, 2008
    Assignee: AZ Electronic Materials USA Corp.
    Inventors: Yasushi Akiyama, Yusuke Takano
  • Patent number: 7364831
    Abstract: A positive resist composition includes a resin component (A) whose alkaline solubility changes by an action of an acid, an acid generator component (B), and polypropylene glycol, wherein the component (A) includes a resin component (A1) including a constitutional unit (a1) represented by general formula (I), a constitutional unit (a2) represented by general formula (II), and a constitutional unit (a3) having an acid dissociable dissolution inhibiting group, wherein R represents a hydrogen atom or a methyl group, and m represents an integer of 1 to 3, wherein R represents a hydrogen atom or a methyl group, and R1 represents alkyl group having a carbon number of 1 to 5, and l represents an integer of 0 to 3.
    Type: Grant
    Filed: May 6, 2005
    Date of Patent: April 29, 2008
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Kouji Yonemura, Taku Nakao
  • Patent number: 7364833
    Abstract: The invention relates to a photoresist composition for an organic layer for a liquid crystal display, which may be used for a large-scale substrate, a spin-less coating method using the composition, a method for fabricating an organic layer pattern, and a liquid crystal display having the organic layer pattern. In particular, the liquid crystal display photoresist composition comprises an organic polymer resin having an average molecular weight in the range of about 2,000 to about 20,000, a mixed solvent of ethylene diglycol methylethyl ether (EDM) and a solvent having a vapor pressure lower than the EDM, and a photosensitizer.
    Type: Grant
    Filed: May 24, 2005
    Date of Patent: April 29, 2008
    Assignee: Samsung Electronics Co., Ltd
    Inventors: Yeong-beom Lee, Seon-su Sin
  • Patent number: 7358033
    Abstract: A dye-containing curable composition including a binder and a dye that is soluble in an organic solvent, in which the binder contains a structural unit represented by the following general formula (I) and has a glass transition temperature in a range of 0 to 250° C.
    Type: Grant
    Filed: June 6, 2003
    Date of Patent: April 15, 2008
    Assignee: FUJIFILM Corporation
    Inventor: Katsumi Araki
  • Patent number: 7358029
    Abstract: A photoresist composition including a polymer, a photoacid generator and a dissolution modification agent, a method of forming an image using the photoresist composition and the dissolution modification agent composition. The dissolution modification agent is insoluble in aqueous alkaline developer and inhibits dissolution of the polymer in the developer until acid is generated by the photoacid generator being exposed to actinic radiation, whereupon the dissolution modifying agent, at a suitable temperature, becomes soluble in the developer and allows the polymer to dissolve in the developer. The DMAs are glucosides, cholates, citrates and adamantanedicarboxylates protected with acid-labile ethoxyethyl, tetrahydrofuranyl, and angelicalactonyl groups.
    Type: Grant
    Filed: September 29, 2005
    Date of Patent: April 15, 2008
    Assignee: International Business Machines Corporation
    Inventors: Robert David Allen, Phillip Joe Brock, Richard Anthony DiPietro, Ratnam Sooriyakumaran, Hoa D. Truong
  • Patent number: 7351515
    Abstract: A positive resist composition includes: (A) a resin capable of increasing a solubility thereof in an alkali developer by an action of an acid; (B) a compound capable of generating a sulfonic acid represented by the following formula (I) upon irradiation with one of an actinic ray and a radiation; and (C1) at least one of an amine compound having at least an aliphatic hydroxyl group in a molecule and an amine compound having at least an ether bond in a molecule: A1A2-SO3H)n ??(I) wherein A1 represents an n-valent linking group, A2 represents a single bond or a divalent aliphatic group, and A2's each may be the same or different, provided that at least one group represented by A1 or A2 contains a fluorine atom, and n represents an integer of from 2 to 4.
    Type: Grant
    Filed: September 16, 2004
    Date of Patent: April 1, 2008
    Assignee: FUJIFILM Corporation
    Inventors: Shoichiro Yasunami, Kenji Wada, Kunihiko Kodama, Kenichiro Sato
  • Patent number: 7344820
    Abstract: The present invention relates to a chemically amplified polymer having a pendent group with dicyclohexyl bonded thereto, a process for the preparation thereof, and a resist composition comprising it, and more particularly, to a novel (meth)acrylic or norbornene carboxylate compound with dicyclohexyl bonded thereto, a process for the preparation thereof, a chemically amplified polymer synthesized therewith, and a positive photoresist composition for ArF comprising said polymer, with high resolution and excellent etching resistance.
    Type: Grant
    Filed: November 19, 2002
    Date of Patent: March 18, 2008
    Assignee: DongJin Semichem Co., Ltd.
    Inventors: Eun-Kyung Son, Jae-Hyun Kang, Deog-Bae Kim, Jae-Hyun Kim
  • Patent number: 7341818
    Abstract: The disclosed invention relates to novel norborne-type monomers containing pendent lactone or sultone groups. The invention also relates to norborne-type polymers and copolymers containing pendent lactone or sultone groups. These polymers and copolymers are useful in making photoimagable materials. The photoimagable materials are particularly suitable for use in photoresist compositions useful in 193 and 157 nm photolithography.
    Type: Grant
    Filed: January 10, 2005
    Date of Patent: March 11, 2008
    Assignee: Promerus LLC
    Inventors: Xiaoming Wu, Larry F. Rhodes, Lawrence Seger
  • Patent number: 7341817
    Abstract: A photosensitive composition comprising a compound capable of generating a specific sulfonic acid upon irradiation with actinic rays or a radiation; a compound capable of generating a specific sulfonic acid upon irradiation with an actinic ray or a radiation; and a pattern forming method using a photosensitive composition comprising a compound capable of generating a specific sulfonic acid upon irradiation with an actinic ray or a radiation.
    Type: Grant
    Filed: November 22, 2004
    Date of Patent: March 11, 2008
    Assignee: FUJIFILM Corporation
    Inventors: Kenji Wada, Kunihiko Kodama
  • Patent number: 7338748
    Abstract: The present invention provides a planographic printing plate precursor including on a support a photosensitive layer that contains a polymerizable composition containing a specific binder polymer having a repeating unit of formula (I), an infrared absorbent, a polymerization initiator and a polymerizable compound, wherein R1 represents a hydrogen atom or a methyl group; R2 represents a linking group which includes two or more atoms selected from a carbon atom, a hydrogen atom, an oxygen atom, a nitrogen atom and a sulfur atom and has a number of atoms of 2 to 82; A represents an oxygen atom or —NR3— in which R3 represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms; and n represents an integer of 1 to 5. The invention also provides a planographic printing plate precursor provided with a specific photosensitive layer with respect to an alkaline developer.
    Type: Grant
    Filed: September 30, 2003
    Date of Patent: March 4, 2008
    Assignee: FUJIFILM Corporation
    Inventors: Atsushi Sugasaki, Kazuto Kunita, Kazuhiro Fujimaki
  • Patent number: 7338745
    Abstract: Positive-working imageable elements comprise a radiation absorbing compound and inner and outer layers on a substrate having a hydrophilic surface. The inner layer comprises a polymeric material that is removable using an alkaline developer and comprises a backbone and attached groups represented by the following Structure Q: wherein L1, L2, and L3 independently represent linking groups, T1, T2, and T3 independently represent terminal groups, and a, b, and c are independently 0 or 1. The imageable elements have improved resistance to development and printing chemicals and solvents.
    Type: Grant
    Filed: January 23, 2006
    Date of Patent: March 4, 2008
    Assignee: Eastman Kodak Company
    Inventors: Kevin B. Ray, Ting Tao, Scott A. Beckley
  • Patent number: 7338755
    Abstract: The photosensitive composition of the invention contains a polymer material having a group having a structure represented by following general formula (2), and a photo acid generator generating acid with an ultraviolet ray or an ionizing radiation wherein m represents an integer of 0 or more.
    Type: Grant
    Filed: May 22, 2007
    Date of Patent: March 4, 2008
    Assignee: Kabushiki Kaisha Toshiba
    Inventor: Satoshi Saito
  • Patent number: 7335457
    Abstract: A positive-tone radiation-sensitive resin composition containing an anthracene-based carboxylic acid component with low sublimation properties and excellent compatibility with other components is provided. The composition exhibits optimum controllability of radiation transmittance as a chemically amplified positive-tone resist effectively responding to active radiation, particularly to deep ultraviolet rays, effectively controlling line width variation in resist patterns due to fluctuation in the resist film thickness on a highly refractive substrate, and exhibiting excellent focal depth allowance. The composition comprises (A) an anthracene derivative of the following formula (1), (B) a photoacid generator comprising a sulfonimide compound, and, (C) a resin containing an acid-dissociable group, wherein R1 is a hydrogen atom or a monovalent organic group, R2 is a monovalent organic group, e is an integer of 0-3, and f is an integer of 0-8.
    Type: Grant
    Filed: September 27, 2005
    Date of Patent: February 26, 2008
    Assignee: JSR Corporation
    Inventors: Daisuke Shimizu, Tomoki Nagai, Yuuji Yada, Kentarou Gotou
  • Patent number: 7335458
    Abstract: A chemically amplified positive resist composition is provided comprising (A) a resin containing acid labile groups other than acetal type which changes its solubility in an alkaline developer as a result of the acid labile groups being eliminated under the action of acid and (B) specific sulfonium salts as a photoacid generator. The composition is improved in resolution and focus latitude, minimized in line width variation and profile degradation even on prolonged PED, improved in pattern profile after development, minimized in pattern feature size variation within the wafer plane by uneven development and thus best suited in the deep-UV lithography.
    Type: Grant
    Filed: February 15, 2006
    Date of Patent: February 26, 2008
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Kazunori Maeda, Satoshi Watanabe
  • Patent number: 7332253
    Abstract: A radiation-sensitive composition and negative-working imageable element includes a polymeric binder comprising pendant allyl ester groups to provide solvent resistance, excellent digital speed (sensitivity) and can be imaged and developed without a preheat step to provide lithographic printing plates. The polymeric binder can be prepared with a precursor polymer having pendant carboxy groups that are converted to allyl ester groups using an allyl-containing halide in the presence of a base in order to avoid gelation.
    Type: Grant
    Filed: July 27, 2006
    Date of Patent: February 19, 2008
    Assignee: Eastman Kodak Company
    Inventors: Ting Tao, Scott A. Beckley
  • Patent number: 7332258
    Abstract: A positive resist composition comprising (A) a resin that contains a repeating unit represented by formula (1) defined in the specification and a repeating unit represented by formula (2) defined in the specification, and is insoluble or slightly soluble in an alkali developer and becomes soluble in an alkali developer by an action of an acid, and (B) a compound generating a sulfonic acid compound represented by formula (3) defined in the specification upon irradiation of actinic ray or radiation.
    Type: Grant
    Filed: September 16, 2004
    Date of Patent: February 19, 2008
    Assignee: FUJIFILM Corporation
    Inventors: Shoichiro Yasunami, Koji Shirakawa
  • Patent number: 7326510
    Abstract: Mixed carbocycle derivatives containing at least two carbocycles per molecule from the group of anthracenes, adamantanes and steroids with functionalized carbon chains are synthesized and used as modifiers of resist properties and especially etch resistance enhancement and absorption characteristics. These derivatives are characterized by formulas I-V, where A and R may be an anthryl- and/or an adamantyl- and/or a steroid moiety. Methods for the preparation of the above compounds are disclosed.
    Type: Grant
    Filed: October 31, 2002
    Date of Patent: February 5, 2008
    Inventors: Evangelos Gogolides, Panagiotis Argitis, Elias Andrea Couladouros, Veroniki Petrou Vidali, Maria Vasilopoulou, George Cordoyiannis
  • Patent number: 7326515
    Abstract: There is provided a positive type resin composition comprising (A) a resin component comprising within the principal chain a structural unit derived from a (meth)acrylate ester and incorporating an acid dissociable, dissolution inhibiting group containing a polycyclic group on an ester side chain section, for which the solubility in alkali increases under the action of acid, (B) an acid generator component which generates acid on exposure, and (C) an organic solvent, wherein the component (A) comprises both a structural unit derived from a methacrylate ester and a structural unit derived from an acrylate ester. According to such a resist composition, a resist pattern can be formed which displays little surface roughness and line edge roughness on etching, and also offers excellent resolution and a wide depth of focus range.
    Type: Grant
    Filed: December 7, 2004
    Date of Patent: February 5, 2008
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Takeshi Iwai, Naotaka Kubota, Satoshi Fujimura, Miwa Miyairi, Hideo Hada
  • Patent number: 7326518
    Abstract: Chemically-amplified positive photoresist compositions are provided that contain a resin that comprises acetal and alicyclic groups. Photoresists of the invention can exhibit notably enhanced lithographic properties. Preferred photoresists of the invention comprise one or more photoacid generator compounds and one or more phenolic resins comprise one or more photoacid-labile acetal groups and one or more alicyclic groups such as adamantyl.
    Type: Grant
    Filed: November 23, 2005
    Date of Patent: February 5, 2008
    Assignee: Rohm and Haas Electronic Materials LLC
    Inventors: James F. Cameron, Dong Woo Lee, Peter Trefonas, III, Gary J. Swanson, Jin Wuk Sung
  • Patent number: 7323289
    Abstract: Novel anti-reflective coatings comprising small molecules (e.g., less than about 5,000 g/mole) in lieu of high molecular weight polymers and methods of using those coatings are provided. In one embodiment, aromatic carboxylic acids are used as the chromophores, and the resulting compounds are blended with a crosslinking agent and an acid. Anti-reflective coating films prepared according to the invention exhibit improved properties compared to high molecular weight polymeric anti-reflective coating films. The small molecule anti-reflective coatings have high etch rates and good via fill properties. Photolithographic processes carried out with the inventive material result in freestanding, 110-nm profiles.
    Type: Grant
    Filed: October 6, 2003
    Date of Patent: January 29, 2008
    Assignee: Brewer Science Inc.
    Inventors: Charles J. Neef, Mandar Bhave, Michelle Fowler, Michelle Windsor
  • Patent number: 7323286
    Abstract: A photosensitive composition, comprises (A) a sulfonium salt represented by formula (I); wherein Y1, Y2 and Y3 each independently represents a nitrogen-containing heteroaryl group, an alkyl group, a cycloalkyl group, an aryl group or an alkenyl group, at least one of Y1, Y2 and Y3 represents a nitrogen-containing heteroaryl group, and at least two of Y1, Y2 and Y3 may combine with each other to form a ring; Xn? represents an n-valent non-nucleophilic anion; and n represents an integer of 1 to 3.
    Type: Grant
    Filed: April 19, 2005
    Date of Patent: January 29, 2008
    Assignee: FUJIFILM Corporation
    Inventor: Kunihiko Kodama
  • Patent number: 7323287
    Abstract: There is provided a positive type resin composition comprising (A) a resin component comprising within the principal chain a structural unit derived from a (meth)acrylate ester and incorporating an acid dissociable, dissolution inhibiting group containing a polycyclic group on an ester side chain section, for which the solubility in alkali increases under the action of acid, (B) an acid generator component which generates acid on exposure, and (C) an organic solvent, wherein the component (A) comprises both a structural unit derived from a methacrylate ester and a structural unit derived from an acrylate ester. According to such a resist composition, a resist pattern can be formed which displays little surface roughness and line edge roughness on etching, and also offers excellent resolution and a wide depth of focus range.
    Type: Grant
    Filed: February 2, 2006
    Date of Patent: January 29, 2008
    Assignee: Tokyo Ohka Kogyo Co., Ltd
    Inventors: Takeshi Iwai, Naotaka Kubota, Satoshi Fujimura, Miwa Miyairi, Hideo Hada
  • Patent number: 7323232
    Abstract: To provide a resin composition for spacer useful for the formation of a pixel-patterned spacer on a substrate in a liquid crystal display device, a spacer using the composition, and a liquid crystal display device that can display high-quality images, a resin composition for spacer contains at least one resin selected from (1) an allyl-containing resin, (2) an allyl-and-hydroxyl-containing resin, and (3) a resin mixture of an allyl-containing resin and a hydroxyl-containing resin.
    Type: Grant
    Filed: October 30, 2003
    Date of Patent: January 29, 2008
    Assignee: FUJIFILM Corporation
    Inventors: Akihiko Takeda, Yoshio Sakakibara
  • Patent number: 7316889
    Abstract: There is provided a positive type resin composition comprising (A) a resin component comprising within the principal chain a structural unit derived from a (meth)acrylate ester and incorporating an acid dissociable, dissolution inhibiting group containing a polycyclic group on an ester side chain section, for which the solubility in alkali increases under the action of acid, (B) an acid generator component which generates acid on exposure, and (C) an organic solvent, wherein the component (A) comprises both a structural unit derived from a methacrylate ester and a structural unit derived from an acrylate ester. According to such a resist composition, a resist pattern can be formed which displays little surface roughness and line edge roughness on etching, and also offers excellent resolution and a wide depth of focus range.
    Type: Grant
    Filed: February 2, 2006
    Date of Patent: January 8, 2008
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Takeshi Iwai, Naotaka Kubota, Satoshi Fujimura, Miwa Miyairi, Hideo Hada
  • Patent number: 7316888
    Abstract: There is provided a positive type resin composition comprising (A) a resin component comprising within the principal chain a structural unit derived from a (meth)acrylate ester and incorporating an acid dissociable, dissolution inhibiting group containing a polycyclic group on an ester side chain section, for which the solubility in alkali increases under the action of acid, (B) an acid generator component which generates acid on exposure, and (C) an organic solvent, wherein the component (A) comprises both a structural unit derived from a methacrylate ester and a structural unit derived from an acrylate ester. According to such a resist composition, a resist pattern can be formed which displays little surface roughness and line edge roughness on etching, and also offers excellent resolution and a wide depth of focus range.
    Type: Grant
    Filed: February 2, 2006
    Date of Patent: January 8, 2008
    Assignee: Tokyo Ohka Kogyo Co., Ltd
    Inventors: Takeshi Iwai, Naotaka Kubota, Satoshi Fujimura, Miwa Miyairi, Hideo Hada