Sulfur In Heterocyclic Ring Patents (Class 430/922)
  • Publication number: 20030194634
    Abstract: A novel anthracene derivative useful as an additive to a radiation-sensitive resin composition is disclosed.
    Type: Application
    Filed: March 6, 2003
    Publication date: October 16, 2003
    Inventors: Tomoki Nagai, Tsutomu Shimokawa
  • Publication number: 20030190554
    Abstract: A plate-making method of a printing plate comprising exposing a printing plate precursor having a photosensitive layer comprising a photopolymerizable composition containing (i) a crosslinking agent having two ethylenic polymerizable groups and (ii) a crosslinking agent having three or more ethylenic polymerizable groups, and development processing the exposed printing plate precursor with an alkali developer having a pH of not more than 12.5.
    Type: Application
    Filed: August 29, 2002
    Publication date: October 9, 2003
    Inventor: Kazuto Kunita
  • Publication number: 20030180635
    Abstract: A visible radiation sensitive composition is disclosed. The composition comprises at least one ethylenically unsaturated monomer capable of free radical initiated addition polymerization; optionally, at least one binder; and a photoinitiator system comprising a coinitiator and a cyanopyridone sensitizer. The coinitiator preferably comprises a metallocene and an onium compound.
    Type: Application
    Filed: February 12, 2002
    Publication date: September 25, 2003
    Inventors: Harald Baumann, Michael Flugel
  • Publication number: 20030165776
    Abstract: A negative resist composition comprising (A) an alkali-soluble polymer, (B) a cross-linking agent forming cross-links between molecules of the alkali-soluble polymer (A) under the action of an acid and (C) a specified acid generator, which can satisfy all of performance requirements concerning sensitivity, resolution, pattern profile and line-edge roughness in the pattern formation by irradiation with electron beams or X-rays.
    Type: Application
    Filed: December 30, 2002
    Publication date: September 4, 2003
    Applicant: FUJI PHOTO FILM CO., LTD.
    Inventors: Shoichiro Yasunami, Kunihiko Kodama
  • Patent number: 6605409
    Abstract: A positive resist composition comprising (A) a compound generating a specific sulfonimide compound by irradiation with an actinic ray or a radiation and (B) a resin having a group, which is decomposed by the action of an acid to increase the solubility of the composition in an alkali developer. The resist composition has an improved resolving power and an improved process allowance such as exposure margin and the depth of focus in a lithographic technique using a light source of short wavelengths capable of super fine working and a positive chemically amplified resist.
    Type: Grant
    Filed: May 21, 2001
    Date of Patent: August 12, 2003
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kunihiko Kodama, Shinichi Kanna
  • Patent number: 6602647
    Abstract: The present invention relates to a photo acid generator which has high transparency to exposure light and also has excellent heat stability in a photoresist composition for lithography using far ultraviolet light, especially light of ArF excimer laser. The photo acid generator contains a sulfonium salt compound represented by the following general formula (1): wherein R1 represents an alkylene group, or an alkylene group having an oxo group, R2 represents a straight-chain, branched-chain, monocyclic, polycyclic or bridged cyclic alkyl group having an oxo group, or a straight-chain, branched-chain, monocyclic, polycyclic or bridged cyclic alkyl group, provided that either of R1 and R2 has an oxo group, and Y− represents a counter ion.
    Type: Grant
    Filed: December 13, 2000
    Date of Patent: August 5, 2003
    Assignee: NEC Corporation
    Inventors: Shigeyuki Iwasa, Katsumi Maeda, Kaichiro Nakano, Etsuo Hasegawa
  • Publication number: 20030134227
    Abstract: New photoacid generator compounds (“PAGs”) are provided and photoresist compositions that comprise such compounds. In particular, cyclic sulfonium and sulfoxonium PAGs are provided. PAGs of the invention are particularly useful as photoactive components of photoresists imaged at short wavelengths such as 248 nm, 193 nm and 157 nm.
    Type: Application
    Filed: October 7, 2002
    Publication date: July 17, 2003
    Inventors: James F. Cameron, Gerhard Pohlers, Yasuhiro Suzuki
  • Publication number: 20030118939
    Abstract: The present invention provides an IR-sensitive composition, which includes: a polymeric binder; and a free radical polymerizable system consisting of: at least one component selected from unsaturated free radical polymerizable monomers, oligomers which are free radical polymerizable and polymers containing C═C bonds in the backbone and/or in the side chain groups; and an initiator system, which includes: (a) at least one compound capable of absorbing IR radiation; (b) at least one compound capable of producing radicals; and (c) at least one carboxylic co-initiator, provided that the total acid number of the polymeric binder is 70 mg KOH/g or less. The present invention further provides a printing plate precursor, a process for preparing the printing plate and a method of producing an image.
    Type: Application
    Filed: November 9, 2001
    Publication date: June 26, 2003
    Applicant: KODAK POLYCHROME GRAPHICS, L.L.C.
    Inventors: Heidi Munnelly, Paul West
  • Publication number: 20030077540
    Abstract: A positive photosensitive composition comprising (A) a specific acid generator that generates an acid upon irradiation of an actinic ray or radiation, and (B) a resin that has a monocyclic or polycyclic alicyclic hydrocarbon structure and is decomposed by the action of an acid to increase solubility in an alkali developing solution.
    Type: Application
    Filed: May 21, 2002
    Publication date: April 24, 2003
    Applicant: FUJI PHOTO FILM CO., LTD.
    Inventors: Kunihiko Kodama, Kenichiro Sato, Toru Fujimori
  • Publication number: 20020164541
    Abstract: Photoresist polymers, and photoresist compositions using the polymer are disclosed. More specifically, photoresist polymers containing maleimide represented by Formula 1. Photoresist compositions including the photoresist polymers have excellent etching resistance, heat resistance and adhesiveness, and development ability in aqueous tetramethylammonium hydroxide (TMAH) solution. As the compositions have low light absorbance at 193 nm and 157 nm wavelength, they are suitable for a process using ultraviolet light source such as VUV (157 nm).
    Type: Application
    Filed: March 27, 2002
    Publication date: November 7, 2002
    Inventors: Geun Su Lee, Jae Chang Jung, Ki Soo Shin
  • Publication number: 20020146641
    Abstract: A chemically amplifying type positive resist composition suitable for use in the lithography utilizing an ArF or KrF excimer laser and excellent in the shape of profile is provided, which comprises a resin which has an alkali-soluble group protected by 2-alkyl-2-adamantyl group or 1-adamantyl-1-alkylalkyl group, and which, per se, is insoluble or slightly soluble in alkali but becomes soluble in alkali by the action of an acid; and a sulfonium salt acid generating agent represented by the following formula (I): 1
    Type: Application
    Filed: November 16, 2001
    Publication date: October 10, 2002
    Inventors: Yasunori Uetani, Kenji Ohashi, Hiroshi Moriuma
  • Publication number: 20020132181
    Abstract: A radiation-sensitive resin composition comprising: (A) an acid-dissociable group-containing resin, insoluble or scarcely soluble in alkali but becoming soluble in alkali when the acid-dissociable group dissociates, and containing recurring units with specific structures and (B) a photoacid generator of the formula (3), 1
    Type: Application
    Filed: January 16, 2002
    Publication date: September 19, 2002
    Inventors: Yukio Nishimura, Masafumi Yamamoto, Atsuko Kataoka, Toru Kajita
  • Publication number: 20020076651
    Abstract: A composition useful for a thick-film negative resist comprising a mixture of at least one epoxidized polyfunctional bisphenol A formaldehyde novolak resin and at least one photoacid generator in a coating solvent, a majority amount of said coating solvent being cyclopentanone.
    Type: Application
    Filed: December 26, 2000
    Publication date: June 20, 2002
    Applicant: MicroChem Corp., a Corporation of the State of Massachussets
    Inventors: Rodney J. Hurditch, Daniel J. Nawrocki, Donald W. Johnson
  • Patent number: 6406830
    Abstract: A chemical amplifying type positive resist composition having high transmittance, superior in sensitivity and resolution in a lithography utilizing a light having a wavelength of 220 nm or lower and confering a good profile is provided, Which comprises an aliphatic sulfonium salt represented by the following formula (I): wherein either Q1, Q2, Q3 and Q4 represent an alkyl group or a cycloalkyl group, or Q1 and Q2 and/or Q3 and Q4 form, together with the adjacent sulfur atom, a heterocyclic group, and m represents an integer of 1 to 8; at least one onium salt selected from the group consisting of a triphenylsulfonium salt and a diphenyliodonium salt; and a resin which contains a polymerization unit having a group unstable to an acid, and which is insoluble in alkali by itself but becomes soluble in alkali by the action of an acid.
    Type: Grant
    Filed: May 7, 2001
    Date of Patent: June 18, 2002
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Hiroki Inoue, Yasunori Uetani
  • Publication number: 20020045121
    Abstract: A self-contained photosensitive material comprising: a support; an imaging layer on the support, the imaging layer comprising a developer material and a plurality of photosensitive microcapsules encapsulating a photosensitive composition and a color precursor; and a protective coating on the imaging layer, the protective coating comprising a cured film of a water-soluble or water-dispersible resin, wherein upon image-wise exposing the imaging layer to actinic radiation and rupturing the microcapsules, the color precursor is released from the microcapsules and reacts with the developer material to form a color image is disclosed.
    Type: Application
    Filed: January 16, 2001
    Publication date: April 18, 2002
    Inventors: Tetsuya Higuchi, Takahiro Uchibori
  • Publication number: 20020015913
    Abstract: A chemical amplifying type positive resist composition which provides a resist pattern having an exceedingly improved line edge roughness, and is excellent in various resist performances such as dry etching resistance, sensitivity and resolution; and comprises:
    Type: Application
    Filed: June 22, 2001
    Publication date: February 7, 2002
    Inventors: Yasunori Uetani, Kenji Oohashi, Akira Kamabuchi
  • Patent number: 6280905
    Abstract: A photosensitive resin composition which comprises (1) a particulate copolymer comprising 10-99.8% by mole of the unit of (i) an aliphatic conjugated diene monomer, 0.1-30% by mole of the unit of (ii) a monomer having one polymerizable unsaturated group and an amino group, 0.1-20% by mole of the unit of (iii) a monomer having at least two polymerizable unsaturated groups and 0-40% by mole of the unit of (iv) a copolymerizable other monomer having one polymerizable unsaturated group, (2) a photopolymerizable unsaturated monomer and (3) a photopolymerization initiator typically represented by 9-fluorenone or 2-i-propylthioxanthone. A photosensitive resin composition is provided which can be developed by using water, has a low hardness and high resilience, and is excellent in balance of properties.
    Type: Grant
    Filed: April 21, 2000
    Date of Patent: August 28, 2001
    Assignee: JSR Corporation
    Inventors: Katsuo Koshimura, Tsukasa Toyoshima, Takashi Nishioka, Tadaaki Tanaka
  • Patent number: 6242158
    Abstract: To provide a photosensitive resin composition and a photosensitive element using the resin composition with excellent sensitivity and adhesion as well as high resolution and plating resistance. A photosensitive resin composition, comprises (A) a polymer carrying carboxyl groups, (B) a compound carrying at least one ethylene-based unsaturated group in the molecule, and (C) a photopolymerization initiator, characterized by the fact that component (B) contains at least 60 weight % of methacrylate (B1) carrying at least one ethylene-based unsaturated group with respect to the total amount of component (B), that the amount of component (C) is in the range of 0.01-20 weight units with respect to 100 weight units of component (A) and component (B), and that component (C) contains 2-5 weight units of lophine dimer (C1) and 0.1-2.0 weight units of triphenylphosphine (C2) with respect to 100 weight units of component (A) and component (B), as well as a photosensitive element using the resin composition.
    Type: Grant
    Filed: August 28, 1998
    Date of Patent: June 5, 2001
    Assignee: Nichigo-Morton Co., Ltd.
    Inventors: Eiji Kosaka, Shigeru Murakami
  • Patent number: 6187511
    Abstract: There is described a method of preparing a positive working water-less lithographic plate which comprises a support having an oleophilic surface, there being coated on the support a mixture which comprises as one component an ink-repellant and water-repellant polymer or a mixture of such polymers or polymer precursors, and as the other essential component of the mixture an infra-red or heat sensitive composition selected from (a) an organic solvent soluble diazo compound and an infra-red absorbing compound, (b) a photopolymer and an infra-red absorbing dye, or (c) a mixture of a free-radically polymerisable ethylenically unsaturated compound or compounds together with either a photoinitiator which is infra-red sensitive or an initiator which is heat sensitive together with an infra-red absorbing compound, the ratio of ink-repellant polymer to infra-red or heat sensitive composition (a), (b) or (c) in the mixture being from 20-80 ink repellant polymer to 80-20 infra-red or heat sensitive composition by weight,
    Type: Grant
    Filed: February 11, 1998
    Date of Patent: February 13, 2001
    Assignee: Kodak Polychrome Graphics LLC
    Inventors: Peter Andrew Reath Bennett, Carole-Anne Smith
  • Patent number: 6136498
    Abstract: A photoresist composition for use in lithographic processes in the fabrication of semiconductor devices such as integrated circuit structures is disclosed. The photoresist composition includes a monomeric sensitizer bounding to a base-soluble long chain polymer.
    Type: Grant
    Filed: June 28, 1996
    Date of Patent: October 24, 2000
    Assignee: International Business Machines Corporation
    Inventors: Premlatha Jagannathan, Leo L. Linehan, Wayne M. Moreau, Randolph J. Smith
  • Patent number: 6127091
    Abstract: A photopolymerizable composition, which contains a polymeric binder, a compound which can be polymerized by free radicals and has at least one terminal ethylenic double bond and a photoinitiator combination comprising an N-heterocyclic compound, a thioxanthone derivative and a dialkylamino compound, is highly photosensitive and produces photoresist stencils with vertical side walls.
    Type: Grant
    Filed: November 3, 1997
    Date of Patent: October 3, 2000
    Assignee: Morton International, Inc.
    Inventors: Ulrich Geissler, Hans-Dieter Frommeld, Hans Ruckert
  • Patent number: 6120973
    Abstract: A radiation sensitive composition comprising (A) a colorant such as carbon black and an organic pigment, (B) an alkali-soluble resin comprising a copolymer of an N-substituted maleimide monomer and other copolymerizable monomer,(C) a polyfunctional monomer, and (D) a photopolymerization initiator.
    Type: Grant
    Filed: April 22, 1998
    Date of Patent: September 19, 2000
    Assignee: JSR Corporation
    Inventors: Kouji Itano, Shigeru Abe, Yasumi Itano
  • Patent number: 6114091
    Abstract: A photopolymerizable composition, which contains a polymeric binder, a compound which can be polymerized by free radicals and has at least one terminal ethylenic double bond and a photoinitiator combination comprising an N-heterocyclic compound, a thioxanthone derivative and a dialkylamino compound, is highly photosensitive and produces photoresist stencils with vertical side walls.
    Type: Grant
    Filed: November 3, 1997
    Date of Patent: September 5, 2000
    Assignee: Morton International, Inc.
    Inventors: Ulrich Geissler, Hans-Dieter Frommeld, Hans Ruckert
  • Patent number: 6114092
    Abstract: A photosensitive resin composition for photoresist which is highly sensitive and can directly form an image using a laser is disclosed. Said composition comprises (A) an unsaturated resin having carboxyl group(s) which is obtained by firstly reacting 0.8 to 1.3 moles of an ethylenic unsaturated monocarboxylic acid with 1 mole of an epoxy group of a homopolymer or copolymer of ethylenic unsaturated monomer having an epoxy group to obtain an unsaturated resin which is then reacted with a dibasic acid anhydride, (B) ethylenic unsaturated compound without epoxy group, and (C) photopolymerization initiator.
    Type: Grant
    Filed: September 29, 1998
    Date of Patent: September 5, 2000
    Assignee: Kansai Paint Co., Ltd.
    Inventors: Kenji Miyagawa, Kenji Seko
  • Patent number: 6110646
    Abstract: A positive photosensitive composition comprising an alkali-soluble organic high molecular substance having phenolic hydroxyl groups and an acid color forming dye.
    Type: Grant
    Filed: August 13, 1998
    Date of Patent: August 29, 2000
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Toshiyuki Urano, Etsuko Hino
  • Patent number: 6037098
    Abstract: Provided is a positive photosensitive composition which has high photosensitivity, is capable of giving an excellent resist pattern, and changes little with time after exposure. The positive photosensitive composition comprises a resin having group(s) capable of decomposing by the action of an acid to enhance solubility of the resin in an alkaline developing solution and a compound represented by formula (Ia) or (Ib) which is capable of generating a sulfonic acid upon irradiation with actinic rays or a radiation: ##STR1## wherein R.sub.1 to R.sub.3 each represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a hydroxy group, a halogen atom, or a group represented by --S--R.sub.4, where R.sub.4 represents an alkyl group or an aryl group; X.sup.- represents the specific anion of a benzenesulfonic, naphthalenesulfonic, or anthracenesulfonic acid; and l, m, and n represents an integer of 1 to 3.
    Type: Grant
    Filed: March 30, 1998
    Date of Patent: March 14, 2000
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Toshiaki Aoai, Satoshi Takita
  • Patent number: 5965324
    Abstract: A light sensitive composition and a manufacturing method of a planographic printing plate employing the same are disclosed, the composition comprising a radical generating agent and a dye represented by the following formula (1), (2) or (3): ##STR1##
    Type: Grant
    Filed: July 18, 1997
    Date of Patent: October 12, 1999
    Assignee: Konica Corporation
    Inventors: Kimihiko Okubo, Noritaka Nakayama
  • Patent number: 5962189
    Abstract: A photosensitive composition can be used to prepare negative-working photosensitive elements such as lithographic printing plates. The composition includes a first photocrosslinkable aromatic resin having photocrosslinkable groups and a number average molecular weight of at least about 1500. Also included is a polymerizable monomer, a photocrosslinkable polyester, a photoinitiator, and an aromatic thiazoline photosensitizer. The photosensitive resins are present at a total weight ratio to the monomer of at least 1.5:1.
    Type: Grant
    Filed: December 19, 1996
    Date of Patent: October 5, 1999
    Assignee: Kodak Polychrome Graphics LLC
    Inventor: Thap DoMinh
  • Patent number: 5932393
    Abstract: The invention relates to photopolymerizable compositions comprising as photoinitiator a borate of the formula I or I' ##STR1## in which R.sub.1, R.sub.2 and R.sub.3 are, for example and independently of one another, phenyl or another aromatic hydrocarbon, with or without any heteroatoms, which radicals are unsubstituted or are substituted, or the radicals R.sub.1 and R.sub.2 form bridges to produce structures of the formulae II, IIa or IIb ##STR2## with the provisos that not more than two of the radicals R.sub.1, R.sub.2 and R.sub.3 are identical and either at least two of the radicals R.sub.1, R.sub.2 and R.sub.3 are aromatic hydrocarbon radicals or phenyl radicals which are substituted in both ortho-positions or at least one radical R.sub.1, R.sub.2 or R.sub.3 is a sterically bulky aryl radical and the remaining radicals of R.sub.1, R.sub.2 and R.sub.3 are aromatic hydrocarbon radicals or are phenyl radicals which are substituted in at least one ortho-position; R.sub.4 is, for example, phenyl or C.sub.1 -C.
    Type: Grant
    Filed: November 21, 1996
    Date of Patent: August 3, 1999
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Allan Francis Cunningham, Martin Kunz, Hisatoshi Kura
  • Patent number: 5863699
    Abstract: A photosensitive composition for forming a pattern through a light-exposure with either one of ArF excimer laser and F.sub.2 excimer laser, which comprises a compound having either an acid-decomposable or acid-crosslinkable group, and a compound represented by the following general formula (1): ##STR1## wherein Ar.sup.1 and Ar.sup.2 are individually an aromatic ring or condensed aromatic ring, R.sup.1 and R.sup.2 are individually halogen atoms or monovalent organic group, X is a group selected from the group consisting of CF.sub.3 SO.sub.3, CH.sub.3 SO.sub.3, CF.sub.3 COOH, ClO.sub.4, SbF.sub.6 and AsF.sub.6, Z is a group selected from the group consisting of Cl, Br, I, S--R and Se--R (R is an alkyl group having 1 to 10 carbon atoms or perfluoroalkyl group having 1 to 10 carbon atoms), and m and n are 0 or a positive integer.
    Type: Grant
    Filed: October 9, 1996
    Date of Patent: January 26, 1999
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Koji Asakawa, Toru Ushirogochi, Naomi Shida, Makoto Nakase
  • Patent number: 5783353
    Abstract: A sealed self-contained photohardenable imaging assembly comprising:a first transparent polymeric film support;a second polymeric film support which may be opaque or transparent;an imaging layer disposed between said first transparent support and said second support;a subbing layer disposed between said first transparent support and said imaging layer, said subbing including a polymer having chemical moieties which bond to said microcapsules; and an adhesive material disposed between said imaging layer and said second support;said imaging layer comprising a developer material and a plurality of microcapsules, said microcapsules encapsulating a photohardenable composition containing a color precursor, a polyethylenically unsaturated compound, a cyanine dye/borate photoinitiator and a disulfide having the formula: ##STR1## where X is selected from the group consisting of S and O except X is N when the disulfide includes one or more tetrazolyl groups; n represents 0 or 1; A represents the residue of the ring con
    Type: Grant
    Filed: December 11, 1995
    Date of Patent: July 21, 1998
    Assignee: Cycolor, Inc.
    Inventors: Joseph C. Camillus, Mark A. Johnson, John M. Taylor, Darrell A. Terry, William Lippke, S. Thomas Brammer
  • Patent number: 5770345
    Abstract: The sensitivity of a photoresist to actinic light is improved by the addition of certain dyes. The photoresist includes a polymer matrix, a photosensitive acid generator and at least one compound selected from the group consisting of dyes containing at least one heterosulphur atom such as 2,2.sup.1,5.sup.1,2"-terthiophene and its derivatives; thianthrene and its derivatives, and 4,6-diphenylthieno(3,4-d)-1,3-dioxol-2-one-5,5-dioxide; phenylsulfone and its derivatives; and 4,5-diphenyl-1,3-dioxol-2-one; 3,4-bis(acetoxymethyl)furan; chelidonic acid and its derivatives; and 5,7,12,14-pentacenetetrone. Resist images on a substrate are formed from the compositions.
    Type: Grant
    Filed: July 16, 1996
    Date of Patent: June 23, 1998
    Assignee: International Business Machines Corporation
    Inventors: Edward Darko Babich, Karen Elizabeth Petrillo, John Patrick Simons, David Earle Seeger
  • Patent number: 5753412
    Abstract: The sensitivity of a photoresist to actinic light is improved by the addition of certain dyes. The photoresist includes a polymer matrix, a photosensitive acid generator and at least one compound selected from the group consisting of dyes containing at least one heterosulphur atom such as 2,2.sup.1,5.sup.1,2"-terthiophene and its derivatives; thianthrene and its derivatives, and 4,6-diphenylthieno(3,4-d)-1,3-dioxol-2-one-5,5-dioxide; phenylsulfone and its derivatives; and 4,5-diphenyl-l,3-dioxol-2-one; 3,4-bis(acetoxymethyl)furan; chelidonic acid and its derivatives; and 5,7,12,14-pentacenetetrone. Resist images on a substrate are formed from the compositions.
    Type: Grant
    Filed: June 5, 1996
    Date of Patent: May 19, 1998
    Assignee: International Business Machines Corporation
    Inventors: Edward Darko Babich, Karen Elizabeth Petrillo, John Patrick Simons, David Earle Seeger
  • Patent number: 5627011
    Abstract: The invention relates to the use of oxime sulfonates of formula 1 ##STR1## wherein R is naphthyl, ##STR2## Ar is an unsubstituted aryl group or an aryl group which carries one or more than one substituent selected from the group consisting of nitro, chloro, bromo, hydroxyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 perfluoroalkyl, C.sub.1 -C.sub.4 alkoxy and acid degradable substituents;R.sub.0 is either a R.sub.1 --X group or R.sub.2 ;X is an oxygen or a sulfur atom;R.sub.1 is hydrogen, C.sub.1 -C.sub.4 alkyl or unsubstituted phenyl or phenyl which is substituted by a member selected from the group consisting of chloro, bromo, C.sub.1 -C.sub.4 alkyl and C.sub.1 -C.sub.4 alkoxy, andR.sub.2 is hydrogen, C.sub.1 -C.sub.
    Type: Grant
    Filed: May 12, 1995
    Date of Patent: May 6, 1997
    Assignee: Ciba-Geigy Corporation
    Inventors: Norbert Munzel, Reinhard Schulz, Heinz Holzwarth, Stephan Ilg
  • Patent number: 5593812
    Abstract: The sensitivity of a photoresist to actinic light is improved by the addition of certain dyes. The photoresist includes a polymer matrix, a photosensitive acid generator and at least one compound selected from the group consisting of dyes containing at least one heterosulphur atom such as 2,2.sup.1,5.sup.1,2"-terthiophene and its derivatives; thianthrene and its derivatives, and 4,6-diphenylthieno(3,4-d)-1,3-dioxol-2-one-5,5-dioxide; phenylsulfone and its derivatives; and 4,5-diphenyl-1,3-dioxol-2-one; 3,4-bis(acetoxymethyl)furan; chelidonic acid and its derivatives; and 5,7,12,14-pentacenetetrone. Resist images on a substrate are formed from the compositions.
    Type: Grant
    Filed: February 17, 1995
    Date of Patent: January 14, 1997
    Assignee: International Business Machines Corporation
    Inventors: Edward D. Babich, Karen E. Petrillo, John P. Simons, David E. Seeger
  • Patent number: 5576146
    Abstract: A photosensitive polymer-containing system containing: (a) an energy sensitive polymer having a linear hydrocarbyl backbone and pendant peptide groups with free-radically polymerizable functionality attached thereto; (b) a vinyl-halomethyl-s-triazine capable of free-radical generation upon excitation with electromagnetic radiation having a wavelength of from about 330 to 500 nm; (c) an organic acid having a pKa of from about 1.8 to 5.5; (d) a leuco dye; and (e) a binder. A colorant may optionally be added. The photosensitive systems exhibit an increased shelf-life and excellent photosensitivity.
    Type: Grant
    Filed: January 17, 1995
    Date of Patent: November 19, 1996
    Assignee: Imation Corp.
    Inventor: M. Zaki Ali
  • Patent number: 5543262
    Abstract: A light sensitive composition which is capable of photopolymerization which includes a photopolymerizable compound a free radical generating component and a benzanthrone or substituted benzanthrone which substantially prevents photopolymerization when the light sensitive composition is exposed to actinic radiation below a threshold amount but permits photopolymerization when the light sensitive composition is exposed to actinic radiation above a threshold amount. This achieves a gate effect which eliminates or decreases unwanted partial exposure in the nonimage areas and hence improves reproduction quality.
    Type: Grant
    Filed: February 24, 1995
    Date of Patent: August 6, 1996
    Assignee: International Paper Company
    Inventors: Maria T. Sypek, John R. Delude, Paul A. Perron
  • Patent number: 5474876
    Abstract: A radiation-crosslinkable mixture which contains a carboxyl-containing precursor of a heterocyclic polymer, a copolymerizable ethylenically unsaturated ternary sulfonium salt, a photoinitiator and a polar aprotic organic solvent.
    Type: Grant
    Filed: October 5, 1994
    Date of Patent: December 12, 1995
    Assignee: BASF Lacke + Farben AG
    Inventors: Hans-Joachim Haehnle, Manfred Schwarz, Rainer Blum
  • Patent number: 5457003
    Abstract: A resist material comprises a polysiloxane obtained by hydrolysis and condensation with dehydration of one or more alkoxysilanes having an oxirane ring, or of a mixture of the alkoxysilane(s) having an oxirane ring and one or more alkoxysilanes having no oxirane ring, and an acid generator. The resist material may contain one or more of a spectral sensitizer, an organic polymer having a hydroxyl group or an epoxy compound. Resist patterns are formed by coating an organic polymer on a substrate and then the resist material on the film of the organic polymer to form a two layer resist having a bottom layer of the organic polymer and top layer of the resist material, prebaking, imagewise exposing high radiation, postbaking, and developing the resist with alkaline solutions to remove an unexposed portion of the top layer, and dry etching the bottom layer using the relic of the resist material as a mask. the temperature of the post baking is preferably lower than that of the prebaking.
    Type: Grant
    Filed: July 30, 1993
    Date of Patent: October 10, 1995
    Assignee: Nippon Telegraph and Telephone Corporation
    Inventors: Akinobu Tanaka, Hiroshi Ban, Jiro Nakamura, Takao Kimura, Yoshio Kawai
  • Patent number: 5447797
    Abstract: A reaction resin mixture, which is able to be hardened thermally and by means of UV radiation, contains the following constituents:a cationically polymerizable epoxide resin;a latent hardening initiator in the form of an aralkyl-thiolanium salt; anda sensitizer of the structure ##STR1## A being --CO--, --NR-- and --CO--CO--, and D being --O--, --S--, --CO-- and --CH.sub.2).sub.x (where x= 1 or 2) or rather a single bond or two hydrogen atoms.
    Type: Grant
    Filed: August 9, 1993
    Date of Patent: September 5, 1995
    Assignee: Siemens Aktiengesellschaft
    Inventors: Bernhard Stapp, Lothar Schoen, Volker Muhrer
  • Patent number: 5391465
    Abstract: A method is provided for using selected photoactive compounds in acid hardening photoresists to produce thermally stable, high resolution images with near ultraviolet exposing radiation. These photoactive compounds can be used as photosensitizers for halogen-containing photoacid generators which by themselves do not otherwise generate sufficient acid upon exposure to near ultraviolet radiation to catalyze the crosslinking of acid hardening resins. The photoactive compounds are selected from the group consisting of phenothiazine, derivatives of phenothiazine, and phenoxazine.
    Type: Grant
    Filed: April 19, 1990
    Date of Patent: February 21, 1995
    Assignee: Rohm and Haas Company
    Inventor: Wayne E. Feely
  • Patent number: 5346801
    Abstract: An image forming process of an image forming material comprising a support and provided thereon, a photosensitive layer and a covering layer in that order comprises imagewise exposing the material by laser beam scanning, and peeling the covering film from the exposed material to form an image on the support or on the covering film, wherein said photosensitive layer contains a colorant, an addition-polymerizable or cross-linkable compound and a salt of a cationic dye with a borate anion represented by the following Formula (1):Formula (1) ##STR1##
    Type: Grant
    Filed: March 18, 1993
    Date of Patent: September 13, 1994
    Assignee: Konica Corporation
    Inventors: Hiroshi Watanabe, Tatsuichi Maehashi, Koichi Nakatani, Katsunori Kato, Tawara Komamura
  • Patent number: 5298364
    Abstract: Sulfonic acid esters of 2,4-bistrichloromethyl-6-(mono- or dihydroxyphenyl)-1,3,5-triazine are disclosed. Also disclosed is a negative-working radiation-sensitive mixture containing such a compound in combination with a compound containing at least two acid-crosslinkable groups, and a water-insoluble polymeric binder which is soluble or at least swellable in aqueous alkaline solutions. The esters are esters of a sulfonic acid or sulfonic acids of the formula R--SO.sub.3 H or R'(--SO.sub.3 H).sub.2 with 2,4-bistrichloromethyl-6-(mono- or dihydroxyphenyl)-1,3,5-triazine of the formulae I and/or II ##STR1## where R is an optionally further substituted (C.sub.1 -C.sub.10)-alkyl, (C.sub.5 -C.sub.10)cycloalkyl, (C.sub.6 -C.sub.10)aryl, (C.sub.6 -C.sub.10)aryl-(C.sub.1 -C.sub.10)alkyl or (C.sub.3 -C.sub.9)heteroaryl radical, R' is an optionally substituted (C.sub.1 -C.sub.10)alkylene, (C.sub.6 -C.sub.10)arylene or (C.sub.3 -C.sub.9)heteroarylene radical, and n may be 1 or 2.
    Type: Grant
    Filed: June 9, 1992
    Date of Patent: March 29, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Georg Pawlowski, Horst Roeschert, Walter Spiess, Klaus-Juergen Przybilla
  • Patent number: 5286603
    Abstract: A radiation sensitive plate comprises a substrate coated with a photopolymerisable composition. The composition comprises a polymerisable compound containing ethylenic unsaturation, a perester photoinitiator and optionally an optical sensitiser. The substrate may be a sheet of grained and anodised aluminum and the plate is useful in the production of lithographic printing plates.
    Type: Grant
    Filed: June 3, 1992
    Date of Patent: February 15, 1994
    Assignee: Vickers PLC
    Inventors: John R. Wade, Rodney M. Potts, Michael J. Pratt
  • Patent number: 5256520
    Abstract: Photopolymerizable compositions containing photoinitiator systems that absorb in the visible are disclosed. The photopolymerizable compositions contain at least one ethylenically unsaturated monomer capable of free radical initiated addition polymerization and a photoinitiator system capable of being activated by actinic radiation. The photoinitiator system comprises a hexaarylbisimidazole, a chain transfer agent, and a sensitizer given by the formulae A or B wherein X and R.sub.1 -R.sub.13 are as defined herein.
    Type: Grant
    Filed: November 10, 1992
    Date of Patent: October 26, 1993
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: William K. Smothers
  • Patent number: 5238782
    Abstract: A photopolymerizable composition comprises at least one addition polymerizable compound having at least one ethylenically unsaturated bond and at least one photopolymerization initiator represented by the following general formula (I): ##STR1## wherein R.sub.1 to R.sub.4 independently represent hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, hydroxyl group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted amino group with the proviso that R.sub.1 to R.sub.4 may form a non-metallic ring together with the carbon atoms bonded thereto; R.sub.5 and R.sub.6 each represents hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a heteroaromatic group, an acyl group, cyano group, an alkoxycarbonyl group, carboxyl group or a substituted alkenyl group with the proviso that R.sub.5 and R.sub.
    Type: Grant
    Filed: February 26, 1990
    Date of Patent: August 24, 1993
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Koichi Kawamura, Mitsuru Koike
  • Patent number: 5212046
    Abstract: A photoacid-generating photoresist composition sensitized with an aromatic, multi-ring, heterocylcic nitrogen containing sensitizer, preferably a ring extended phenothiazine derivative. The use of the sensitizer permits exposure of photoresists to near UV irradiation where such photoresists have heretofore been exposed to deep UV irradiation. The invention is especially useful for acid hardening photoresist systems.
    Type: Grant
    Filed: June 28, 1991
    Date of Patent: May 18, 1993
    Assignee: Shipley Company Inc.
    Inventors: Angelo A. Lamola, Gary Calabrese, Roger Sinta
  • Patent number: 5198323
    Abstract: A resist composition comprising an alkali-soluble resin, a 1,2-quinone diazide compound and a compound of the general formula (I): ##STR1## wherein Z is an oxygen or sulfur atom or a group of the formula: >N--R.sub.4 in which R.sub.4 is a hydrogen atom or an alkyl group; R.sub.1, R.sub.2 and R.sub.3 are the same or different and independently a hydrogen atom, a substituted or unsubstituted alkyl group, a halogen atom, a hydroxyl group, a cyano group or a group of the formula: --OCOR" in which R" is a substituted or unsubstituted alkyl group; and X and Y are independently a cyano group or a group of the formula: ##STR2## --COOR or --CONHR' in R is an alkyl group and R' is a hydrogen atom or an aryl group, which is suitable for the formation of very fine patterns on a substrate having a high reflectance.
    Type: Grant
    Filed: April 30, 1991
    Date of Patent: March 30, 1993
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Teijiro Kitao, Masaru Matsuoka, Ryotaro Hanawa, Yasunori Uetani, Naoki Takeyama, Takeshi Hioki, Hiroshi Takagaki
  • Patent number: 5141840
    Abstract: A light-sensitive composition comprising:(a) a polysiloxane compound having at least 1 mol % of a structural unit derived from a product of a thermal cycloaddition reaction between a compound of formula (I), (II), (III) or (IV) and a compound of formula (V), (VI), (VII) or (VIII), and(b) an onium salt compound.
    Type: Grant
    Filed: January 29, 1991
    Date of Patent: August 25, 1992
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kazuyoshi Mizutani, Toshiaki Aoai
  • Patent number: 5130227
    Abstract: A radiation sensitive plate comprises a substrate coated with a photopolymerizable composition. The composition comprises a polymerizable compound containing ethylenic unsaturation, a perester photoinitiator and optionally an optical sensitiser. The substrate may be a sheet of grained and anodized aluminum and the plate is useful in the production of lithographic printing plates.
    Type: Grant
    Filed: October 5, 1989
    Date of Patent: July 14, 1992
    Assignee: Vickers Plc
    Inventors: John R. Wade, Rodney M. Potts, Michael J. Pratt