Nitrogen Compound Containing Patents (Class 430/919)

Cross-Reference Art Collections

Nitrogen in heterocyclic ring (Class 430/920)
  • Patent number: 8198011
    Abstract: A method of making imaged elements such as lithographic printing plates is achieved by imagewise exposing a positive-working imageable element using energy of less than 300 mJ/cm2 to provide exposed and non-exposed regions. The imaged element is developed using an alkaline, silicate-free solution containing a carbonate to remove predominantly only the exposed regions to provide an image. The imageable element comprises a substrate and a radiation absorbing compound, and has an imageable layer on the substrate that comprises a developability-enhancing compound and a poly(vinyl acetal) in which at least 25 mol % of its recurring units comprise pendant nitro-substituted phenolic groups.
    Type: Grant
    Filed: February 4, 2008
    Date of Patent: June 12, 2012
    Assignee: Eastman Kodak Company
    Inventors: Moshe Levanon, Moshe Nakash, Tanya Kurtser
  • Patent number: 8182979
    Abstract: A photopolymerization initiator is provided. The photopolymerization initiator contains at least one unsaturated double bond and at least one oxime ester group in the molecule. The photopolymerization initiator comprises a compound represented by Formula 1 or 2: wherein R1 and R2 are each independently —CH3, —C2H5, —C3H7 or —C6H5; wherein R3, R4 and R5 are each independently —CH3, —C2H5, —C3H7 or —C6H5. Further provided is a photosensitive resin composition comprising the photopolymerization initiator. The use of the photosensitive resin composition in photolithography reduces the formation of volatile residue during post-development baking.
    Type: Grant
    Filed: October 30, 2009
    Date of Patent: May 22, 2012
    Assignee: LG Chem, Ltd.
    Inventors: Keon Woo Lee, Raisa Kharbash, Chang Ho Cho, Sung Hyun Kim, Sang Kyu Kwak, Dong Kung Oh, Chang Soon Lee
  • Patent number: 8173350
    Abstract: An oxime compound represented by the formula (I): wherein Y represents an unsubstituted or substituted n-valent C6-C14 aromatic hydrocarbon group, n represents an integer of 1 to 6, R1 represents a C1-C30 aliphatic hydrocarbon group etc., R2 represents a linear or branched chain C1-C20 aliphatic hydrocarbon group etc., W represents —CO—O— etc., Q1 and Q2 each independently represent a fluorine atom etc., Z represents a C1-C20 halogenated aliphatic hydrocarbon group etc, and the resist composition containing the same.
    Type: Grant
    Filed: July 21, 2009
    Date of Patent: May 8, 2012
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tatsuro Masuyama, Kazuhiko Hashimoto, Takashi Hiraoka, Ichiki Takemoto
  • Patent number: 8173351
    Abstract: A compound shown by the following formula (1) can be used as a material for a radiation-sensitive composition capable of forming a resist film which effectively responds to electron beams or the like, exhibits low roughness, and can form a high precision minute pattern in a stable manner.
    Type: Grant
    Filed: January 8, 2008
    Date of Patent: May 8, 2012
    Assignee: JSR Corporation
    Inventors: Daisuke Shimizu, Ken Maruyama, Toshiyuki Kai, Tsutomu Shimokawa
  • Patent number: 8148044
    Abstract: A positive photosensitive composition includes at least one compound that when exposed to actinic rays or radiation, generates any of the sulfonic acids of general formula (I) and a resin whose solubility in an alkali developer is increased by the action of an acid, wherein each of X1 and X2 independently represents a fluorine atom or a fluoroalkyl group, R1 represents a group with a polycyclic structure, provided that the polycyclic structure may have a substituent, and R2 represents a hydrogen atom, a chain alkyl group, a monocyclic alkyl group, a group with a polycyclic structure or a monocyclic aryl group, provided that each of the chain alkyl group, monocyclic alkyl group, polycyclic structure and monocyclic aryl group may have a substituent, and provided that R1 and R2 may be bonded to each other to thereby form a polycyclic structure.
    Type: Grant
    Filed: October 29, 2009
    Date of Patent: April 3, 2012
    Assignee: Fujifilm Corporation
    Inventors: Shuhei Yamaguchi, Tomotaka Tsuchimura, Yuko Tada
  • Patent number: 8137892
    Abstract: Disclosed is a photobase generator comprising a compound having a nitrogen atom and a conjugated multiple bond.
    Type: Grant
    Filed: December 12, 2007
    Date of Patent: March 20, 2012
    Assignee: Asahi Kasei Chemicals Corporation
    Inventors: Katsuya Shimizu, Fumio Matsushita
  • Patent number: 8133656
    Abstract: An oxime ester compound represented by general formula (I): wherein R1 and R2 each independently represent R11, OR11, COR11, SR11, CONR12R13, or CN; R11, R12, and R13 each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms, R3 and R4 each independently represent R11, OR11, SR11, COR11, CONR12R13, NR12COR11, OCOR11, COOR11, SCOR11, OCSR11, COSR11, CSOR11, CN, a halogen atom, or a hydroxyl group; a and b each independently represent 0 to 4; X represents an oxygen atom, a sulfur atom, a selenium atom, CR31R32, CO, NR33, or PR34; R31, R32, R33, and R34 each independently represent R11, OR11, COR11, SR11, CONR12R13, or CN.
    Type: Grant
    Filed: December 21, 2007
    Date of Patent: March 13, 2012
    Assignee: Adeka Corporation
    Inventors: Daisuke Sawamoto, Koichi Kimijima
  • Patent number: 8124310
    Abstract: A positive resist composition includes: (A) a resin containing a repeating unit represented by formula (I) or (I?) as defined in the specification, of which solubility in an alkali developer increases under an action of an acid; and (B) a compound capable of generating an acid upon irradiation with actinic rays or radiation: and a pattern forming method uses the positive resist composition.
    Type: Grant
    Filed: September 26, 2008
    Date of Patent: February 28, 2012
    Assignee: Fujifilm Corporation
    Inventors: Shuji Hirano, Shinichi Sugiyama
  • Patent number: 8092976
    Abstract: A resist composition containing: a polymer having a group capable of decomposing under an action of an acid and having a weight average molecular weight of from 1,000 to 5,000, of which solubility in an alkali developer increases under an action of an acid; and a compound capable of generating a compound having a structure represented by the following formula (A-I) upon irradiation with actinic rays or radiation: Q1-X1—NH—X2-Q2??(A-I) wherein Q1 and Q2 each independently represents a monovalent organic group, provided that either one of Q1 and Q2 has a proton acceptor functional group, Q1 and Q2 may be combined with each other to form a ring and the ring formed may have a proton acceptor functional group; and X1 and X2 each independently represents —CO— or —SO2—.
    Type: Grant
    Filed: September 28, 2007
    Date of Patent: January 10, 2012
    Assignee: FUJIFILM Corporation
    Inventors: Sou Kamimura, Kenji Wada
  • Patent number: 8088549
    Abstract: Positive-working imageable elements can be imaged and developed to prepare imaged elements such as lithographic printing plates. The imageable elements including an imageable layer that has one or more alkaline soluble polymeric binders and a developability-enhancing compound that is represented by Structure (DEC) or (DEC1) described herein that are organic compounds having at least one amino group and at least one carboxylic acid group in each molecule.
    Type: Grant
    Filed: December 19, 2007
    Date of Patent: January 3, 2012
    Assignee: Eastman Kodak Company
    Inventors: Moshe Levanon, Moshe Nakash
  • Patent number: 8048613
    Abstract: An alkali development-type solder resist includes (A) a carboxyl group-containing photosensitive resin obtained by reacting (a) a compound having two or more cyclic ether or thioether groups in the molecule with (b) an unsaturated monocarboxylic acid, reacting the product with (c) a polybasic acid anhydride, reacting the resulting resin with (d) a compound having a cyclic ether group and an ethylenic unsaturated group in the molecule, and reacting the product additionally with (c) a polybasic acid anhydride, (B) an oxime ester-based photopolymerization initiator containing a specific oxime ester group, (C) a compound having two or more ethylenic unsaturated groups in the molecule, and (D) a thermosetting component, wherein the dry film obtained by applying the composition has an absorbance of 0.3 to 1.2 per 25 ?m of the film thickness at a wavelength of 350 to 375 nm.
    Type: Grant
    Filed: October 13, 2008
    Date of Patent: November 1, 2011
    Assignee: Taiyo Ink Mfg. Co., Ltd.
    Inventors: Nobuhito Itoh, Yoko Shibasaki, Kenji Kato, Masao Arima
  • Patent number: 8029971
    Abstract: Compositions, a method, and a photopatternable blend. The compositions include a blend of a first and a second polymer. The first polymer is a substituted silsesquioxane copolymer. The second polymer is a substituted silsesquioxane polymer. The second polymer is configured to undergo chemical crosslinking with the first polymer, the second polymer, or a combination thereof, upon exposure to light, thermal energy, or a combination thereof. The compositions include a photosensitive acid generator. The method includes forming a film. The film is patternwise imaged, and at least one region is exposed to radiation. After the imaging, the film is baked, wherein at least one exposed region is rendered substantially soluble. After the baking, the film is developed, wherein a relief pattern remains. The relief pattern is exposed to radiation. The relief pattern is baked. The relief pattern is cured. A chemically amplified positive-tone photopatternable blend is also described.
    Type: Grant
    Filed: March 13, 2008
    Date of Patent: October 4, 2011
    Assignee: International Business Machines Corporation
    Inventors: Robert D. Allen, Phillip Joe Brock, Blake W. Davis, Qinghuang Lin, Robert D. Miller, Alshakim Nelson, Ratnam Sooriyakumaran
  • Patent number: 8029972
    Abstract: A resist composition including a base component (A) which exhibits changed solubility in an alkali developing solution under action of acid, an acid-generator component (B) which generates acid upon exposure, and a nitrogen-containing organic compound (D1) having a molecular weight of 200 or more, which is represented by general formula (d1) shown below (wherein each of R1 to R3 independently represents a hydrocarbon group which may have a substituent, with the proviso that at least one of R1 to R3 is a polar group-containing hydrocarbon group, at least one of R1 to R3 is a hydrophobic group, and two of R1 to R3 may be bonded to each other to form a ring with the nitrogen atom).
    Type: Grant
    Filed: October 8, 2008
    Date of Patent: October 4, 2011
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Tsuyoshi Nakamura, Hiroaki Shimizu
  • Patent number: 8029975
    Abstract: A resist composition and a method for forming a patterned feature on a substrate. The composition comprises a molecular glass having at least one fused polycyclic moiety and at least one base soluble functional group protected with an acid labile protecting group, and a photosensitive acid generator. The method includes providing a composition including a photosensitive acid generator and a molecular glass having at least one fused polycyclic moiety and at least one base soluble functional group protected with an acid labile protecting group, forming a film of the composition on the substrate, patternwise imaging the film, wherein at least one region of the film is exposed to radiation or a beam of particles, resulting in production of an acid catalyst in the exposed region, baking the film, developing the film, resulting in removal of base-soluble exposed regions, wherein a patterned feature from the film remains following the removal.
    Type: Grant
    Filed: July 24, 2009
    Date of Patent: October 4, 2011
    Assignee: International Business Machines Corporation
    Inventors: James J. Bucchignano, Wu-Song Huang, Pushkara R. Varanasi, Roy R. Yu
  • Patent number: 8026036
    Abstract: The present invention relates to a photosensitive resin composition excellent in pliability, ultraviolet sensitivity for development, developability with an aqueous alkali solution, and storage stability at room temperature and a circuit substrate employing the same. The photosensitive resin composition includes a siloxane-containing polyamic acid resin having structural units respectively represented by the following formulae (1), (2), and (3) and a photopolymerization initiator incorporated therein. The circuit substrate is coated with the photosensitive resin composition.
    Type: Grant
    Filed: March 24, 2006
    Date of Patent: September 27, 2011
    Assignee: Nippon Steel Chemical Co., Ltd.
    Inventors: Kiwamu Tokuhisa, Kentaro Hayashi, Hironobu Kawasato
  • Patent number: 8012671
    Abstract: A curable composition in which polymerization inhibition due to oxygen is suppressed and which may be cured with high sensitivity by exposure to laser light or the like is provided. The curable composition includes: a polymerizable compound having an ethylenically unsaturated bond; a binder; a radical polymerization initiator; and at least one specific amine compound. Also provided is an image forming material and a negative-working planographic printing plate precursor including the curable composition.
    Type: Grant
    Filed: September 24, 2008
    Date of Patent: September 6, 2011
    Assignee: FUJIFILM Corporation
    Inventor: Shigefumi Kanchiku
  • Patent number: 8003294
    Abstract: A photosensitive composition comprises: (A) a compound capable of generating an acid represented by formula (I) upon irradiation with actinic ray or radiation; and (B) a resin that decomposes by the action of an acid to its increase solubility in an alkali developer wherein Ra represents an alkyl group substituted with a fluorine atom, or an aryl group substituted with a fluorine atom or a group having a fluorine atom; Rb represents an alkyl group not substituted with a fluorine atom on ?-position of the alkyl group, or an aryl group not substituted with a fluorine atom or a group having a fluorine atom.
    Type: Grant
    Filed: March 10, 2008
    Date of Patent: August 23, 2011
    Assignee: FUJIFILM Corporation
    Inventor: Kunihiko Kodama
  • Patent number: 7964654
    Abstract: Compounds represented by the following structural formulas can be used as photoacid generators: Such compounds are useful, for example, in fabricating arrays of polymers.
    Type: Grant
    Filed: September 14, 2010
    Date of Patent: June 21, 2011
    Assignee: Affymetrix, Inc.
    Inventors: Glenn H. McGall, Andrea Cuppoletti
  • Patent number: 7960087
    Abstract: A positive photosensitive composition comprising: (A) a resin having at least one repeating unit having a specific lactone structure at a side chain and being capable of decomposing by the action of an acid to increase the solubility in an alkali developer; and (B) a compound capable of generating a specific acid upon irradiation with an actinic ray or a radiation, and a pattern-forming method using the positive photosensitive composition, are provided.
    Type: Grant
    Filed: March 9, 2006
    Date of Patent: June 14, 2011
    Assignee: Fujifilm Corporation
    Inventor: Kunihiko Kodama
  • Patent number: 7955779
    Abstract: A radiation-sensitive composition can be used to prepare positive-working imageable elements having improved solvent resistance and is useful for making lithographic printing plates. The composition includes an alkaline soluble polymeric binder that is a specific poly(vinyl acetal) that exhibits improved resistance to press chemicals, and a radiation absorbing compound.
    Type: Grant
    Filed: August 21, 2009
    Date of Patent: June 7, 2011
    Assignee: Eastman Kodak Company
    Inventors: Moshe Levanon, Emmanuel Lurie, Vladimir Kampel
  • Patent number: 7919225
    Abstract: A method and a composition. The composition includes at least one carbosilane-substituted silsesquioxane polymer which crosslinks in the presence of an acid. The at least one carbosilane-substituted silsesquioxane polymer is soluble in aqueous base. The method includes forming a coating on a substrate. The coating includes one or more carbosilane-substituted silsesquioxane polymers. The carbosilane-substituted silsesquioxane polymer is soluble in aqueous base. The coating is exposed to radiation, resulting in generating a latent pattern in the coating. The exposed coating is baked at a first temperature less than about 150° C. The baked coating is developed, resulting in forming a latent image from the latent pattern in the baked coating. The latent image is cured at a second temperature less than about 500° C.
    Type: Grant
    Filed: May 23, 2008
    Date of Patent: April 5, 2011
    Assignee: International Business Machines Corporation
    Inventors: Robert D. Allen, Phillip Joe Brock, Blake W. Davis, Geraud Jean-Michel Dubois, Qinghuang Lin, Robert D. Miller, Alshakim Nelson, Sampath Purushothaman, Ratnam Sooriyakumaran
  • Patent number: 7883828
    Abstract: Linear or branched functionalized polycarbosilanes having an absorbance less than 3.0 ?m?1 at 193 nm and a relatively high refractive index are provided. The functionalized polycarbosilanes contain at least one pendant group that is acid labile or aqueous base soluble. Also disclosed are photoresists formulations containing the functionalized polycarbosilanes that are suitable for use in lithography, e.g., immersion lithography.
    Type: Grant
    Filed: March 28, 2008
    Date of Patent: February 8, 2011
    Assignee: International Business Machines Corporation
    Inventors: Robert D. Allen, Matthew E. Colburn, Daniel P. Sanders, Ratnam Sooriyakumaran, Hoa D. Truong
  • Patent number: 7871761
    Abstract: Provided is a method for forming a resist lower layer material for use in a multilayer resist process, especially two-layer resist process or three-layer resist process, having a function of neutralizing an amine contaminant from a substrate, thereby reducing a harmful effect such as trailing skirts of a resist pattern of an upper layer resist. Specifically, there is provided a material for forming a lower layer of a chemically amplified photoresist layer comprising a crosslinkable polymer and a thermal acid generator that can generate an acid by heating at 100° C. or greater and is represented by the general formula (1a): R1CF2SO3?(R2)4N+??(1a), as well as a resist lower layer substrate comprising a resist lower layer formed using said material.
    Type: Grant
    Filed: July 27, 2007
    Date of Patent: January 18, 2011
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Toshihiko Fujii, Youichi Ohsawa
  • Patent number: 7867689
    Abstract: A method. The method includes dip coating a film of a composition on a silicon wafer substrate. The composition includes a polymer blend of a first polymer and a second polymer. The first polymer is a substituted silsesquioxane copolymer. The second polymer is a polysilsesquioxane having silanol end groups. The composition includes a photosensitive acid generator, an organic base, and an organic crosslinking agent. The film is patternwise imaged and at least one region is exposed to radiation having a wavelength of about 248 nanometers. The film is baked, resulting in inducing crosslinking in the film. The film is developed resulting in removal of base-soluble unexposed regions of the film, wherein a relief pattern from the film remains. The relief pattern is cured at a temperature between about 300° C. and about 450° C., and the curing utilizes a combination of thermal treatment with UV radiation.
    Type: Grant
    Filed: May 18, 2007
    Date of Patent: January 11, 2011
    Assignee: International Business Machines Corporation
    Inventors: Robert D. Allen, Phillip Brock, Blake W. Davis, Qinghuang Lin, Robert D. Miller, Alshakim Nelson, Ratnam Sooriyakumaran
  • Patent number: 7863344
    Abstract: Compounds represented by the following structural formulas can be used as photoacid generators: Such compounds are useful, for example, in fabricating arrays of polymers.
    Type: Grant
    Filed: November 3, 2008
    Date of Patent: January 4, 2011
    Assignee: Affymetrix, Inc.
    Inventors: Glenn H. McGall, Andrea Cuppoletti
  • Patent number: 7858286
    Abstract: A positive resist composition and method for forming a resist pattern are provided which enable a resist pattern with excellent shape to be obtained.
    Type: Grant
    Filed: April 7, 2006
    Date of Patent: December 28, 2010
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Yohei Kinoshita, Makiko Irie, Waki Ohkubo, Yusuke Nakagawa, Shinichi Hidesaka
  • Patent number: 7858287
    Abstract: A photosensitive resin realizes formation of a pattern having a good shape, without introducing poor compatibility between an acid generator and a photoresist primary-component polymer having an acid-dissociable group, and a photosensitive composition containing the photosensitive resin. The photosensitive resin includes a repeating unit represented by formula (1): (wherein R1 represents a C2-C9 linear or branched divalent hydrocarbon group; each of R2 to R5 represents a hydrogen atom or a C1-C3 linear or branched hydrocarbon group; each of R6 and R7 represents an organic group, wherein R6 and R7 may together form a divalent organic group; and X?represents an anion); at least one of a repeating unit represented by formula (2): (wherein R8 represents a C2-C9 linear or branched hydrocarbon group) and a repeating unit represented by formula (3): a repeating unit represented by formula (4): optionally, a repeating unit represented by formula (5).
    Type: Grant
    Filed: November 30, 2007
    Date of Patent: December 28, 2010
    Assignees: Hyogo Prefecture, Toyo Gosei Co., Ltd
    Inventors: Takeo Watanabe, Hiroo Kinoshita, Shinichi Yusa, Tomotaka Yamanaka, Masamichi Hayakawa, Yosuke Osawa, Satoshi Ogi, Yoshitaka Komuro
  • Patent number: 7833690
    Abstract: The present invention relates to photoacid generating compounds, lithographic resists comprising photoacid generating compounds, and to various lithographic processes techniques, and applications.
    Type: Grant
    Filed: October 6, 2006
    Date of Patent: November 16, 2010
    Assignee: The University of North Carolina at Charlotte
    Inventors: Kenneth E. Gonsalves, Mingxing Wang
  • Patent number: 7781144
    Abstract: The present invention is a positive resist composition and a resist pattern forming method including a resin component (A) which has a polymer compound (A1) having a structural units (a1) including an acetal type acid dissociable, dissolution inhibiting group, a structural unit (a2) derived from an acrylate ester having a lactone-containing polycyclic group, and a structural unit (a3) derived from an acrylate ester having a polar group-containing aliphatic hydrocarbon group, and an acid generator component (B) having an onium salt-based acid generator (B1) having a cation portion represented by a general formula (b-1) shown below [wherein, R11 represents an alkyl group, an alkoxy group, a halogen atom or a hydroxyl group; R12 to R13 each represents, independently, an aryl group or the alkyl group that may have substituent group; n? represents either 0 or an integer from 1 to 3].
    Type: Grant
    Filed: April 18, 2006
    Date of Patent: August 24, 2010
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Yohei Kinoshita, Waki Ohkubo, Yusuke Nakagawa, Shinichi Hidesaka, Makiko Irie
  • Patent number: 7749677
    Abstract: The negative resist composition of the present invention comprises a silsesguioxane resin (A) comprising a constituent unit (a1) represented by the following general formula (I) and a constituent unit (a2) represented by the following general formula (II), an acid generator component (B) which generates an acid upon exposure, and a crosslinking agent component (C): wherein R1 represents a linear or branched alkylene group having 1 to 5 carbon atoms, and
    Type: Grant
    Filed: March 11, 2005
    Date of Patent: July 6, 2010
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventor: Tomoyuki Ando
  • 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: 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: 7718344
    Abstract: A resist composition, includes: (B) a polymer having a group capable of decomposing under an action of an acid and having a weight average molecular weight of 1,000 to 5,000, of which solubility in an alkali developer increases under an action of an acid; and (Z) a compound containing a sulfonium cation having a structure represented by formula (Z-1): wherein Y1 to Y13 each independently represents a hydrogen atom or a substituent, and adjacent members of Y1 to Y13 may combine with each other to form a ring; and Z represents a single bond or a divalent linking group.
    Type: Grant
    Filed: September 28, 2007
    Date of Patent: May 18, 2010
    Assignee: FUJIFILM Corporation
    Inventors: Sou Kamimura, Kenji Wada, Yasutomo Kawanishi
  • Patent number: 7713679
    Abstract: There is provided a compound represented by a general formula (B1-1) shown below, an acid generator composed of the above compound, a resist composition containing an acid generator composed of the above compound, and a method of forming a resist pattern: (wherein RX represents a hydrocarbon group which may contain a substituent group; Q1 represents an alkylene group of 1 to 12 carbon atoms which may contain a substituent group, or a single bond; n represents an integer of 0 or 1; Y1 represents an alkylene group of 1 to 4 carbon atoms, or a fluorinated alkylene group of 1 to 4 carbon atoms; and A+ represents an organic cation which contains a nitrogen atom).
    Type: Grant
    Filed: October 14, 2008
    Date of Patent: May 11, 2010
    Inventors: Keita Ishiduka, Yoshiyuki Utsumi, Akiya Kawaue, Takehiro Seshimo, Hideo Hada
  • Patent number: 7687220
    Abstract: The invention pertain to novel photoacid generator compounds of the formula I, II or III wherein R1 is for example C1-C18alkylsulfonyl or phenylsulfonyl, phenyl-C1-C3alkylsulfonyl, , naphthylsulfonyl, anthracylsulfonyl or phenanthrylsulfonyl, all optionally substituted, or R1 is a group X1, X2 and X3 independently of each other are O or S; R?1, is e.g. phenylenedisulfonyl, naphthylenedisulfonyl, diphenylenedisulfonyl, or oxydiphenylenedisulfonyl, all optionally substituted; R2 is halogen or C1-C10haloalkyl; X is halogen; Ar1 is for example biphenylyl or fluorenyl, or is substituted naphthyl; Ar?1 is heteroarylene, optionally substituted; R8, R9, R10 and R11 for example are C1-C6alkyl which is unsubstituted or substituted by halogen; or R8, R9 and R10 are phenyl which is unsubstituted or substituted by C1-C4alkyl or halogen; or R10 and R11 together are 1,2-phenylene or C2-C6alkylene which is unsubstituted or substituted by C1-C4alkyl or halogen.
    Type: Grant
    Filed: July 11, 2005
    Date of Patent: March 30, 2010
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Hitoshi Yamato, Toshikage Asakura, Tobias Hintermann
  • 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: 7625687
    Abstract: This invention pertains to a silsesquioxane resin with improved lithographic properties (such as etch-resistance, transparency, resolution, sensitivity, focus latitude, line edge roughness, and adhesion) suitable as a photoresist; a method for in-corporating the fluorinated or non-fluorinated functional groups onto silsesquioxane backbone. The silsesquioxane resins of this invention has the general structure (HSiO3/2)a(RSiO3/2)b wherein; R is an acid dissociable group, a has a value of 0.2 to 0.9 and b has a value of 0.1 to 0.8 and 0.9?a+b?1.0.
    Type: Grant
    Filed: June 30, 2004
    Date of Patent: December 1, 2009
    Assignee: Dow Corning Corporation
    Inventors: Sanlin Hu, Eric Scott Moyer, Sheng Wang, David Lee Wyman
  • Patent number: 7601480
    Abstract: The present application relates to a compound of formula where X is selected from the group CF3SO3, C4F9SO3, N(SO2C2F5)2, N(SO2CF3SO2C4F9), N(SO2C3F7)2, N(SO2C4F9)2, CF3CHFO(CF2)2SO3, and CH3CH2CH2O(CF2)4SO3. A photoresist composition comprising a polymer containing an acid labile group, the above compounds, and one or more additional photoacid generators is also provided for.
    Type: Grant
    Filed: December 20, 2006
    Date of Patent: October 13, 2009
    Assignee: AZ Electronic Materials USA Corp.
    Inventors: M. Dalil Rahman, Takanori Kudo
  • 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: 7544462
    Abstract: Radiation-sensitive compositions can be used to prepare positive-working imageable elements useful for example to make lithographic printing plates. The compositions include an aqueous alkaline solvent soluble polymeric binder that includes a phenolic resin (such as a novolak) or a poly(vinyl acetal). The compositions also include a developability-enhancing composition comprising one or more basic nitrogen-containing organic compounds. The radiation-sensitive composition can be coated as an imageable layer that further includes a radiation absorbing compound that is, for example, sensitive to infrared radiation.
    Type: Grant
    Filed: February 22, 2007
    Date of Patent: June 9, 2009
    Assignee: Eastman Kodak Company
    Inventors: Moshe Levanon, Larisa Postel, Marina Rubin, Tanya Kurtser
  • 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: 7521168
    Abstract: A resist composition for an electron beam, EUV or X-ray comprising (A1) a compound that has a reduction potential higher than that of diphenyl iodonium salt and generates an acid upon irradiation of an actinic ray or radiation.
    Type: Grant
    Filed: February 11, 2003
    Date of Patent: April 21, 2009
    Assignee: Fujifilm Corporation
    Inventors: Kazuyoshi Mizutani, Hyou Takahashi
  • Patent number: 7510816
    Abstract: A resist composition is provided comprising a polysiloxane, a specific acid generator, a nitrogen-containing organic compound, and a solvent. The resist composition exerts high-resolution performance without the problem of a T-top profile and is suited for the bilayer resist process using ArF exposure.
    Type: Grant
    Filed: October 4, 2005
    Date of Patent: March 31, 2009
    Assignee: Shin-Estu Chemical Co., Ltd.
    Inventors: Katsuya Takemura, Kazumi Noda, Youichi Ohsawa
  • Patent number: 7498126
    Abstract: A photoacid generator has formula (1). A chemically amplified resist composition comprising the photoacid generator has advantages including a high resolution, focus latitude, long-term PED dimensional stability, and a satisfactory pattern profile shape. When the photoacid generator is combined with a resin having acid labile groups other than those of the acetal type, resolution and top loss are improved. The composition is suited for deep UV lithography.
    Type: Grant
    Filed: June 5, 2007
    Date of Patent: March 3, 2009
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Youichi Ohsawa, Kazunori Maeda, Satoshi Watanabe
  • 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: 7465527
    Abstract: The resist material contains a photo-acid generator having an absorption peak to exposure light having a wavelength of less than 300 nm, and a second photo-acid generator having an absorption peak to exposure light having a wavelength of 300 nm or more. The method for forming a resist pattern comprises a step for selectively exposing which exposes a coating film of the resist material to an exposure light having a wavelength of less than 300 nm, and a step for selectively exposing by using an exposure light having a wavelength of 300 nm or more. The semiconductor device comprises a pattern formed by the resist pattern. The method for forming a semiconductor device comprises a step for forming a resist pattern on an underlying layer by the aforementioned manufacturing method, and a step for patterning the underlying layer by etching using the resist pattern as a mask.
    Type: Grant
    Filed: March 28, 2002
    Date of Patent: December 16, 2008
    Assignee: Fujitsu Limited
    Inventors: Junichi Kon, Ei Yano
  • Patent number: 7462438
    Abstract: A resist film made of a resist material including 4-pentanelactam, that is, hetero cyclic ketone, is formed on a substrate, and subsequently, pattern exposure is performed by irradiating the resist film with exposing light through a mask. Then, the resist film having been subjected to the pattern exposure is developed, thereby forming a resist pattern.
    Type: Grant
    Filed: May 2, 2006
    Date of Patent: December 9, 2008
    Assignee: Panasonic Corporation
    Inventors: Masayuki Endo, Masaru Sasago
  • Patent number: 7449573
    Abstract: A compound which generates a sulfonic acid having one or more —SO3H groups and one or more —SO2— bonds upon irradiation with an actinic ray or a radiation; a photosensitive composition containing the compound; and a method of pattern formation with the photosensitive composition.
    Type: Grant
    Filed: February 14, 2005
    Date of Patent: November 11, 2008
    Assignee: FUJIFILM Corporation
    Inventors: Kunihiko Kodama, Kenji Wada, Kaoru Iwato
  • Patent number: 7422839
    Abstract: The use of a positive resist composition that includes a resin with a specific structure improves the resolution and yields a resist pattern with a favorable shape. In addition, when a resist layer is formed on either a magnetic film or a metallic oxidation prevention film formed on the magnetic film, the layer is less prone to tailing and undercutting phenomena.
    Type: Grant
    Filed: July 5, 2004
    Date of Patent: September 9, 2008
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventor: Hiroshi Shimbori