Sulfur In Heterocyclic Ring Patents (Class 430/922)
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Publication number: 20030194634Abstract: A novel anthracene derivative useful as an additive to a radiation-sensitive resin composition is disclosed.Type: ApplicationFiled: March 6, 2003Publication date: October 16, 2003Inventors: Tomoki Nagai, Tsutomu Shimokawa
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Publication number: 20030190554Abstract: 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: ApplicationFiled: August 29, 2002Publication date: October 9, 2003Inventor: Kazuto Kunita
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Publication number: 20030180635Abstract: 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: ApplicationFiled: February 12, 2002Publication date: September 25, 2003Inventors: Harald Baumann, Michael Flugel
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Publication number: 20030165776Abstract: 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: ApplicationFiled: December 30, 2002Publication date: September 4, 2003Applicant: FUJI PHOTO FILM CO., LTD.Inventors: Shoichiro Yasunami, Kunihiko Kodama
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Patent number: 6605409Abstract: 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: GrantFiled: May 21, 2001Date of Patent: August 12, 2003Assignee: Fuji Photo Film Co., Ltd.Inventors: Kunihiko Kodama, Shinichi Kanna
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Patent number: 6602647Abstract: 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: GrantFiled: December 13, 2000Date of Patent: August 5, 2003Assignee: NEC CorporationInventors: Shigeyuki Iwasa, Katsumi Maeda, Kaichiro Nakano, Etsuo Hasegawa
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Publication number: 20030134227Abstract: 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: ApplicationFiled: October 7, 2002Publication date: July 17, 2003Inventors: James F. Cameron, Gerhard Pohlers, Yasuhiro Suzuki
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Publication number: 20030118939Abstract: 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: ApplicationFiled: November 9, 2001Publication date: June 26, 2003Applicant: KODAK POLYCHROME GRAPHICS, L.L.C.Inventors: Heidi Munnelly, Paul West
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Publication number: 20030077540Abstract: 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: ApplicationFiled: May 21, 2002Publication date: April 24, 2003Applicant: FUJI PHOTO FILM CO., LTD.Inventors: Kunihiko Kodama, Kenichiro Sato, Toru Fujimori
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Publication number: 20020164541Abstract: 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: ApplicationFiled: March 27, 2002Publication date: November 7, 2002Inventors: Geun Su Lee, Jae Chang Jung, Ki Soo Shin
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Publication number: 20020146641Abstract: 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): 1Type: ApplicationFiled: November 16, 2001Publication date: October 10, 2002Inventors: Yasunori Uetani, Kenji Ohashi, Hiroshi Moriuma
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Publication number: 20020132181Abstract: 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), 1Type: ApplicationFiled: January 16, 2002Publication date: September 19, 2002Inventors: Yukio Nishimura, Masafumi Yamamoto, Atsuko Kataoka, Toru Kajita
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Publication number: 20020076651Abstract: 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: ApplicationFiled: December 26, 2000Publication date: June 20, 2002Applicant: MicroChem Corp., a Corporation of the State of MassachussetsInventors: Rodney J. Hurditch, Daniel J. Nawrocki, Donald W. Johnson
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Patent number: 6406830Abstract: 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: GrantFiled: May 7, 2001Date of Patent: June 18, 2002Assignee: Sumitomo Chemical Company, LimitedInventors: Hiroki Inoue, Yasunori Uetani
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Publication number: 20020045121Abstract: 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: ApplicationFiled: January 16, 2001Publication date: April 18, 2002Inventors: Tetsuya Higuchi, Takahiro Uchibori
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Publication number: 20020015913Abstract: 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: ApplicationFiled: June 22, 2001Publication date: February 7, 2002Inventors: Yasunori Uetani, Kenji Oohashi, Akira Kamabuchi
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Patent number: 6280905Abstract: 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: GrantFiled: April 21, 2000Date of Patent: August 28, 2001Assignee: JSR CorporationInventors: Katsuo Koshimura, Tsukasa Toyoshima, Takashi Nishioka, Tadaaki Tanaka
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Patent number: 6242158Abstract: 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: GrantFiled: August 28, 1998Date of Patent: June 5, 2001Assignee: Nichigo-Morton Co., Ltd.Inventors: Eiji Kosaka, Shigeru Murakami
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Patent number: 6187511Abstract: 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: GrantFiled: February 11, 1998Date of Patent: February 13, 2001Assignee: Kodak Polychrome Graphics LLCInventors: Peter Andrew Reath Bennett, Carole-Anne Smith
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Patent number: 6136498Abstract: 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: GrantFiled: June 28, 1996Date of Patent: October 24, 2000Assignee: International Business Machines CorporationInventors: Premlatha Jagannathan, Leo L. Linehan, Wayne M. Moreau, Randolph J. Smith
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Patent number: 6127091Abstract: 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: GrantFiled: November 3, 1997Date of Patent: October 3, 2000Assignee: Morton International, Inc.Inventors: Ulrich Geissler, Hans-Dieter Frommeld, Hans Ruckert
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Patent number: 6120973Abstract: 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: GrantFiled: April 22, 1998Date of Patent: September 19, 2000Assignee: JSR CorporationInventors: Kouji Itano, Shigeru Abe, Yasumi Itano
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Patent number: 6114091Abstract: 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: GrantFiled: November 3, 1997Date of Patent: September 5, 2000Assignee: Morton International, Inc.Inventors: Ulrich Geissler, Hans-Dieter Frommeld, Hans Ruckert
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Patent number: 6114092Abstract: 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: GrantFiled: September 29, 1998Date of Patent: September 5, 2000Assignee: Kansai Paint Co., Ltd.Inventors: Kenji Miyagawa, Kenji Seko
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Patent number: 6110646Abstract: A positive photosensitive composition comprising an alkali-soluble organic high molecular substance having phenolic hydroxyl groups and an acid color forming dye.Type: GrantFiled: August 13, 1998Date of Patent: August 29, 2000Assignee: Mitsubishi Chemical CorporationInventors: Toshiyuki Urano, Etsuko Hino
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Patent number: 6037098Abstract: 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: GrantFiled: March 30, 1998Date of Patent: March 14, 2000Assignee: Fuji Photo Film Co., Ltd.Inventors: Toshiaki Aoai, Satoshi Takita
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Patent number: 5965324Abstract: 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: GrantFiled: July 18, 1997Date of Patent: October 12, 1999Assignee: Konica CorporationInventors: Kimihiko Okubo, Noritaka Nakayama
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Patent number: 5962189Abstract: 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: GrantFiled: December 19, 1996Date of Patent: October 5, 1999Assignee: Kodak Polychrome Graphics LLCInventor: Thap DoMinh
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Patent number: 5932393Abstract: 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: GrantFiled: November 21, 1996Date of Patent: August 3, 1999Assignee: Ciba Specialty Chemicals CorporationInventors: Allan Francis Cunningham, Martin Kunz, Hisatoshi Kura
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Patent number: 5863699Abstract: 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: GrantFiled: October 9, 1996Date of Patent: January 26, 1999Assignee: Kabushiki Kaisha ToshibaInventors: Koji Asakawa, Toru Ushirogochi, Naomi Shida, Makoto Nakase
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Patent number: 5783353Abstract: 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 conType: GrantFiled: December 11, 1995Date of Patent: July 21, 1998Assignee: Cycolor, Inc.Inventors: Joseph C. Camillus, Mark A. Johnson, John M. Taylor, Darrell A. Terry, William Lippke, S. Thomas Brammer
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Patent number: 5770345Abstract: 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: GrantFiled: July 16, 1996Date of Patent: June 23, 1998Assignee: International Business Machines CorporationInventors: Edward Darko Babich, Karen Elizabeth Petrillo, John Patrick Simons, David Earle Seeger
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Patent number: 5753412Abstract: 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: GrantFiled: June 5, 1996Date of Patent: May 19, 1998Assignee: International Business Machines CorporationInventors: Edward Darko Babich, Karen Elizabeth Petrillo, John Patrick Simons, David Earle Seeger
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Patent number: 5627011Abstract: 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: GrantFiled: May 12, 1995Date of Patent: May 6, 1997Assignee: Ciba-Geigy CorporationInventors: Norbert Munzel, Reinhard Schulz, Heinz Holzwarth, Stephan Ilg
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Patent number: 5593812Abstract: 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: GrantFiled: February 17, 1995Date of Patent: January 14, 1997Assignee: International Business Machines CorporationInventors: Edward D. Babich, Karen E. Petrillo, John P. Simons, David E. Seeger
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Patent number: 5576146Abstract: 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: GrantFiled: January 17, 1995Date of Patent: November 19, 1996Assignee: Imation Corp.Inventor: M. Zaki Ali
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Patent number: 5543262Abstract: 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: GrantFiled: February 24, 1995Date of Patent: August 6, 1996Assignee: International Paper CompanyInventors: Maria T. Sypek, John R. Delude, Paul A. Perron
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Patent number: 5474876Abstract: 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: GrantFiled: October 5, 1994Date of Patent: December 12, 1995Assignee: BASF Lacke + Farben AGInventors: Hans-Joachim Haehnle, Manfred Schwarz, Rainer Blum
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Patent number: 5457003Abstract: 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: GrantFiled: July 30, 1993Date of Patent: October 10, 1995Assignee: Nippon Telegraph and Telephone CorporationInventors: Akinobu Tanaka, Hiroshi Ban, Jiro Nakamura, Takao Kimura, Yoshio Kawai
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Patent number: 5447797Abstract: 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: GrantFiled: August 9, 1993Date of Patent: September 5, 1995Assignee: Siemens AktiengesellschaftInventors: Bernhard Stapp, Lothar Schoen, Volker Muhrer
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Patent number: 5391465Abstract: 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: GrantFiled: April 19, 1990Date of Patent: February 21, 1995Assignee: Rohm and Haas CompanyInventor: Wayne E. Feely
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Patent number: 5346801Abstract: 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: GrantFiled: March 18, 1993Date of Patent: September 13, 1994Assignee: Konica CorporationInventors: Hiroshi Watanabe, Tatsuichi Maehashi, Koichi Nakatani, Katsunori Kato, Tawara Komamura
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Patent number: 5298364Abstract: 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: GrantFiled: June 9, 1992Date of Patent: March 29, 1994Assignee: Hoechst AktiengesellschaftInventors: Georg Pawlowski, Horst Roeschert, Walter Spiess, Klaus-Juergen Przybilla
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Patent number: 5286603Abstract: 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: GrantFiled: June 3, 1992Date of Patent: February 15, 1994Assignee: Vickers PLCInventors: John R. Wade, Rodney M. Potts, Michael J. Pratt
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Patent number: 5256520Abstract: 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: GrantFiled: November 10, 1992Date of Patent: October 26, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventor: William K. Smothers
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Patent number: 5238782Abstract: 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: GrantFiled: February 26, 1990Date of Patent: August 24, 1993Assignee: Fuji Photo Film Co., Ltd.Inventors: Koichi Kawamura, Mitsuru Koike
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Patent number: 5212046Abstract: 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: GrantFiled: June 28, 1991Date of Patent: May 18, 1993Assignee: Shipley Company Inc.Inventors: Angelo A. Lamola, Gary Calabrese, Roger Sinta
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Patent number: 5198323Abstract: 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: GrantFiled: April 30, 1991Date of Patent: March 30, 1993Assignee: Sumitomo Chemical Co., Ltd.Inventors: Teijiro Kitao, Masaru Matsuoka, Ryotaro Hanawa, Yasunori Uetani, Naoki Takeyama, Takeshi Hioki, Hiroshi Takagaki
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Patent number: 5141840Abstract: 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: GrantFiled: January 29, 1991Date of Patent: August 25, 1992Assignee: Fuji Photo Film Co., Ltd.Inventors: Kazuyoshi Mizutani, Toshiaki Aoai
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Patent number: 5130227Abstract: 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: GrantFiled: October 5, 1989Date of Patent: July 14, 1992Assignee: Vickers PlcInventors: John R. Wade, Rodney M. Potts, Michael J. Pratt