Patents Examined by Rosemary Ashton
  • Patent number: 6699641
    Abstract: Various circuit structures incorporating masks and anti-reflective coatings and methods of fabricating the same are provided. In one aspect, a circuit structure is provided that includes a substrate and a first photosensitive film on the substrate. The first photosensitive film is photosensitive to a first electromagnetic spectrum and anti-reflective of a second electromagnetic spectrum that differs from the first electromagnetic spectrum. A second photosensitive film is on the first photosensitive film. The second photosensitive film is photosensitive to the second electromagnetic spectrum whereby exposure by the second electromagnetic spectrum will activate the second photosensitive film but not the first photosensitive film and exposure by the first electromagnetic spectrum will activate unmasked portions of the first photosensitive film. The first photosensitive film doubles as an anti-reflective coating that may be patterned anisotropically using lithographic techniques.
    Type: Grant
    Filed: December 12, 2001
    Date of Patent: March 2, 2004
    Assignee: Advanced Micro Devices, Inc.
    Inventors: Kay Hellig, Massud Aminpur
  • Patent number: 6696216
    Abstract: Thiophene-containing photo acid generators having either of the following general formulas: wherein at least one of R1, R2 or R3 is thiophene or thiophene that is substituted with alkyl, alkoxy or cycloalkyl, and the remaining R1, R2 or R3, not containing a thiophene moiety, are independently selected from the group consisting of alkyl, cycloalkyl and aryl, or at least one of R1, R2 or R3 are joined together to form a cyclic moiety having from about 4 to about 8 ring carbon atoms; and Y is a counter ion, are disclosed as well as the use thereof as a component of a chemically amplified resist composition. In addition to the thiophene-containing photo acid generator, the inventive composition includes a chemically amplified base polymer, a solvent, an optional photosensitizer, an optional base, an optional dissolution modifying agent and an optional surfactant.
    Type: Grant
    Filed: June 29, 2001
    Date of Patent: February 24, 2004
    Assignee: International Business Machines Corporation
    Inventors: Wenjie Li, Pushkara Rao Varanasi, Kuang-Jung Chen
  • Patent number: 6692889
    Abstract: A polymeric compound of the invention includes at least one monomer unit selected from the following formulae (I), (II), (III) and (IV): (wherein R1 is a hydrogen atom or a methyl group, R2 and R3 are each a hydrogen atom, a hydroxyl group or a —COOR4 group, where R4 is, e.g.
    Type: Grant
    Filed: April 5, 2001
    Date of Patent: February 17, 2004
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Yoshinori Funaki, Kiyoharu Tsutsumi, Akira Takaragi, Keizo Inoue
  • Patent number: 6689536
    Abstract: A resist film is formed by applying, on a substrate, a pattern formation material containing a polymer including a first unit represented by Chemical Formula 1 and a second unit represented by Chemical Formula 2, and an acid generator: wherein R1 and R3 are the same or different and selected from the group consisting of an alkyl group, a chlorine atom and an alkyl group including a fluorine atom; R2 is a protecting group released by an acid; and m is an integer of 0 through 5. Subsequently, the resist film is irradiated with exposing light of a wavelength shorter than a 180 nm band for pattern exposure, and a resist pattern is formed by developing the resist film after the pattern exposure.
    Type: Grant
    Filed: January 3, 2002
    Date of Patent: February 10, 2004
    Assignee: Matsushita Electric Industrial Co., Ltd.
    Inventors: Shinji Kishimura, Masayuki Endo, Masaru Sasago, Masamitsu Shirai, Masahiro Tsunooka
  • Patent number: 6689535
    Abstract: Disclosed is an anti-reflective coating composition for forming an anti-reflective coating as an undercoating layer is provided, comprising a crosslinking agent, which is at least one compound selected from nitrogen-containing compounds having an amino group(s) and/or an imino group(s) at least two hydrogen atoms of which are substituted by a hydroxyalkyl group(s) and/or an alkoxyalkyl group(s), and an acidic compound, wherein the crosslinking agent is such that the proportion of its low-molecular-weight component not larger than a trimer is adjusted to be 15 wt % or less; a multilayer photoresist material using the composition; and a method for forming a pattern. According to the present invention, even in the formation of a hyperfine pattern, it is possible to provide a photoresist pattern having a rectangular cross-sectional profile in relation to the substrate without causing any undesirable phenomena, such as footing, undercutting, etc. at is bottom.
    Type: Grant
    Filed: November 9, 2001
    Date of Patent: February 10, 2004
    Assignee: Tokyo Ohka Kogyo Co., LTD
    Inventors: Etsuko Iguchi, Takeshi Tanaka, Kazumasa Wakiya
  • Patent number: 6689553
    Abstract: A silver halide photographic emulsion that comprises silver halide grains. The emulsion was prepared in the presence of at least one halogen oxoacid salt represented by formula (I) below: M(XOn)m  (I) wherein M represents an alkali metal ion or alkaline-earth metal ion, X represents a halogen atom, n represents 2 or 3, and m represents 1 or 2. A silver halide photographic light-sensitive material that has at least one silver halide emulsion layer on a support. The material contains the above silver halide photographic emulsion.
    Type: Grant
    Filed: March 1, 2001
    Date of Patent: February 10, 2004
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Mamoru Sakurazawa, Takeshi Funakubo, Hirotomo Sasaki, Kiyoshi Morimoto
  • Patent number: 6686125
    Abstract: A lithographic printing plate precursor which comprises a support having provided thereon a layer containing a light-to-heat converting agent as a lower layer and a hydrophilic photosensitive layer containing light-to-heat convertible metallic fine particles which change to hydrophobic with the conversion of light to heat as an upper layer.
    Type: Grant
    Filed: January 10, 2001
    Date of Patent: February 3, 2004
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Satoshi Hoshi, Shingo Ishimaru, Keizo Ogawa, Kouichi Waki, Kiyotaka Fukino
  • Patent number: 6686124
    Abstract: A multifunctional polymer comprising a polymeric chain having chromophore groups and cross-linking sites is suitable as a resist material and especially as the underlayer for bilayer and top surface imaging strategies. The multifunctional polymer can function as an antireflective coating, planarizing layer or etch resistant hard mask.
    Type: Grant
    Filed: March 14, 2000
    Date of Patent: February 3, 2004
    Assignee: International Business Machines Corporation
    Inventors: Marie Angelopoulos, Katherina E. Babich, David R. Medeiros, Wayne M. Moreau
  • Patent number: 6686121
    Abstract: A resist composition is prepared by reacting an alkali-soluble polymer having a phenolic hydroxyl or carboxyl groups with a vinyl ether compound in an aprotic solvent, such as propylene glycol monomethyl ether acetate, in the presence of an acid catalyst, suspending the reaction by the addition of a base, and directly adding a photoacid generator to the reaction solution. When a dialkyl dicarbonate is used in stead of the vinyl ether compound, a resist composition is prepared by carrying out the reaction in the presence of a basic catalyst and adding a photoacid generator directly to the reaction. Thus resist compositions can be prepared without isolating or purifying an alkali-soluble polymer which has been substituted by a catalytic reaction.
    Type: Grant
    Filed: April 2, 2001
    Date of Patent: February 3, 2004
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Hiroshi Okazaki, Georg Pawlowski, Satoru Funato, Yoshiaki Kinoshita, Yuko Yamaguchi
  • Patent number: 6686123
    Abstract: Photoresist monomers of following Formulas 1 and 2, photoresist polymers thereof, and photoresist compositions containing the same. The photoresist composition has excellent adhesiveness to a wafer, and is developable in aqueous tetramethylammonium hydroxide (TMAH) solution. In addition, the photoresist composition has low absorbance of light having the wavelength of 157 nm, and thus is suitable for a photolithography process using ultraviolet light sources such as VUV (157 nm) and EUV (13 nm) in fabricating a minute circuit for a high integration semiconductor device. wherein, R1, R2 and R3 are as defined in the specification of the invention.
    Type: Grant
    Filed: November 9, 2001
    Date of Patent: February 3, 2004
    Assignee: Hynix Semiconductor Inc
    Inventors: Geun Su Lee, Jae Chang Jung, Min Ho Jung
  • Patent number: 6683202
    Abstract: The invention discloses a novel ester compound of an unsaturated carboxylic acid represented by the general formula in which R1 is preferably a hydrogen atom or methyl group, R2 is preferably a trifluoromethyl group, R3 is a non-aromatic polycyclic hydrocarbon group or, preferably, an adamantyl group and R4 is preferably a hydrogen atom or methyl group. This unsaturated ester compound is polymerizable to give a (co)polymeric resin which can be used as a base resinous ingredient in a photoresist composition for light exposure with ultraviolet light of a very short wavelength by virtue of the high transparency to the short-wavelength light. A synthetic method for the preparation of the novel ester compound is disclosed.
    Type: Grant
    Filed: February 22, 2002
    Date of Patent: January 27, 2004
    Assignee: Tokyo Ohka, Kogyo Co., Ltd.
    Inventors: Toshiyuki Ogata, Kotaro Endo, Hiroshi Komano
  • Patent number: 6680160
    Abstract: Anti-reflective coatings formed from new polymers and having high etch rates are provided. Broadly, the coatings are formed from a polymer binder and a light attenuating compound. The polymer binder has halogen atoms bonded thereto, preferably to functional groups on the polymer binder rather than to the polymer backbone. Preferred polymer binders comprise acrylic polymers while it is preferred that the halogenated functional groups of the polymer binders be dihalogenated, and more preferably trihalogenated, with chlorine, fluorine, or bromine atoms.
    Type: Grant
    Filed: June 28, 2002
    Date of Patent: January 20, 2004
    Assignee: Brewer Science, Inc.
    Inventors: Tomoyuki Enomoto, Ken-Ichi Mizusawa, Shin-Ya Arase, Rama Puligadda
  • Patent number: 6680157
    Abstract: The present invention pertains to polymeric compositions useful for the suppression or elimination of outgassing of volatile components generated from photoresist polymers during lithographic construction. In resists of the invention, an aromatic compound is mixed with a photoresist composition, such that the aromatic compound suppresses or eliminates outgassing of volatile components upon exposure of the resist to radiation. The aromatic additive is preferably an aromatic polymer and in at least some instances can be substituted with at least one electron-donating group or electron-withdrawing group to enhance its stabilizing effects. In one embodiment, the aromatic compound can be an additive to a resist composition. In another embodiment, the aromatic compound can be incorporated into the polymeric backbone of the resist composition.
    Type: Grant
    Filed: October 12, 2000
    Date of Patent: January 20, 2004
    Assignee: Massachusetts Institute of Technology
    Inventor: Theodore H. Fedynyshyn
  • Patent number: 6677106
    Abstract: A method for imaging patterning compositions comprising the steps of: (1) providing at least one patterning composition layer on a substrate; said patterning composition comprising: (a) at least one acid generator; (b) at least one cross linking resin or compound; (c) at least one binder resin comprising a polymer containing reactive pendant group selected from group consisting of hydroxyl, carboxylic acid, sulfonamide, active imide, alkoxymethylamides and mixtures thereof; and (d) at least one infrared absorber; (2) imagewise exposing the patterning composition layer to actinic radiation; (3) treating the imaged patterning composition layer with heat energy to treat the imaged portions of the composition layer; (4) flood exposing the heat-treated, imaged patterning composition layer with UV light for a predetermined time, said time being sufficient to promote the effective clear-out of non-imaged portions during the developing step without causing substantial deterioration of the imaged portions; and
    Type: Grant
    Filed: January 3, 2002
    Date of Patent: January 13, 2004
    Assignee: Kodak Polychrome Graphics LLC
    Inventors: Oliver Richard Blum, William Paul Heideman, Dean Ginther, Jeffrey James Collins
  • Patent number: 6677103
    Abstract: Disclosed is a novel chemical-amplification positive-working photoresist composition capable of giving a patterned resist layer with excellent properties such as photosensitivity, pattern resolution, heat resistance and cross sectional profile of the patterned resist layer. The composition is characterized by the use of, as the film-forming resinous component, a hydroxyl-containing resinous ingredient which is a combination of a first resin of which from 30 to 60% of the hydroxyl groups are substituted by acid-dissociable solubility-reducing groups and a second resin of which from 5 to 20% of the hydroxyl groups are substituted by acid-dissociable groups of the same kind as in the first resin in a weight proportion of 1.9 to 9:1.
    Type: Grant
    Filed: April 3, 2002
    Date of Patent: January 13, 2004
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Kazufumi Sato, Satoshi Maemori, Taku Nakao, Kazuyuki Nitta
  • Patent number: 6673512
    Abstract: A chemical amplification system negative-working resist composition for an electron beam and/or an X-ray, which is excellent in sensitivity and resolution and has a rectangular profile, comprising an alkali-soluble resin having structural units represented by the following general formula (a), a compound generating an acid by irradiation of the electron beam or the X-ray, and a crosslinking agent which initiates crosslinking by the acid:
    Type: Grant
    Filed: January 17, 2001
    Date of Patent: January 6, 2004
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kazuya Uenishi, Yutaka Adegawa, Koji Shirakawa
  • Patent number: 6673518
    Abstract: A polymer comprising recurring units of formula (1) wherein R1 is H or methyl, R2 is H or C1-8 alkyl, R3 is hydrogen or CO2R4, and R4 is C1-15 alkyl and recurring units having a carboxylic acid protected with an acid-decomposable protecting group containing an adamantane or tetracyclo-[4.4.0.12,5.17,10]dodecane structure and having a Mw of 1,000-500,000 is novel. A resist composition comprising the polymer as a base resin is sensitive to high-energy radiation, has excellent sensitivity, resolution and etching resistance and lends itself to micropatterning with electron beams or deep-UV.
    Type: Grant
    Filed: June 14, 2002
    Date of Patent: January 6, 2004
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Tsunehiro Nishi, Koji Hasegawa, Takeshi Kinsho
  • Patent number: 6673513
    Abstract: There are provided a photosensitive polymer having a copolymer of alkyl vinyl ether and a resist composition containing the same. The photosensitive polymer includes a copolymer of alkyl vinyl ether and maleic anhydride, represented by the following structure: wherein X is one of a linear alkyl vinyl ether and a cyclic alkyl vinyl ether, which are respectively represented by the structures wherein y is one of the integer values 1 through 4, R1 is one of a hydrogen atom and a methyl group, R2 is a C1 to C20 hydrocarbon, and R3 is one of a hydrogen atom, a C1 to C3 alkyl group and an alkoxy group.
    Type: Grant
    Filed: January 19, 2001
    Date of Patent: January 6, 2004
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Sang-jun Choi, Hyun-woo Kim
  • Patent number: 6673511
    Abstract: Although use of a nitrogen-containing compound as a basic compound component of a resist composition makes it possible to ease the T-top problem at an acid dissociation constant pKa falling within a range of 2 to 6, it is accompanied with the problem that the reaction, that is, acid diffusion upon use of a highly-reactive acid-labile group cannot be controlled. In order to overcome this problem, one or more basic compounds selected from those represented by the following formulas (I) to (III) and (1) to (4) are employed.
    Type: Grant
    Filed: October 27, 2000
    Date of Patent: January 6, 2004
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Jun Hatakeyama, Youichi Ohsawa, Takeru Watanabe
  • Patent number: 6670101
    Abstract: The invention is a process for building-up printed wiring boards using metal foil coated with toughened benzocyclobutene-based dielectric polymers. The invention is also a toughened dielectric polymer comprising benzocyclobutene-based monomers or oligomers, ethylenically unsaturated polymer additive, and, optionally, a photoactive compound.
    Type: Grant
    Filed: January 10, 2002
    Date of Patent: December 30, 2003
    Assignee: Dow Global Technologies Inc.
    Inventors: Kaoru Ohba, Hideki Akimoto, Philip E. Garrou, Ying-Hung So, Britton Lee Kaliszewski