With Inhibitor Or Stabilizer Patents (Class 430/917)
Cross-Reference Art Collections
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Patent number: 8883023Abstract: A method for forming a pattern includes providing a composition to form a resist underlayer film on a surface of a substrate to be processed. The composition contains a calixarene based compound having a group represented by a following formula (i) bound to at least a part of an aromatic ring or at least a part of a heteroaromatic ring of the calixarene based compound. The resist underlayer film on the surface of the substrate is treated with heat or an acid. A resist pattern is formed on a surface of the resist underlayer film. The resist underlayer film and the substrate are etched using the resist pattern as a mask to form the pattern on the substrate. The dry-etched resist underlayer film is removed from the substrate with a basic solution.Type: GrantFiled: September 28, 2012Date of Patent: November 11, 2014Assignee: JSR CorporationInventors: Goji Wakamatsu, Hayato Namai, Syun Aoki
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Patent number: 8580479Abstract: Technologies are generally described for a photoresist and methods and systems effective to form a pattern in a photoresist on a substrate. In some examples, the photoresist includes a resin, a photoinitiator and a photoinhibitor. The photoinitiator may be effective to generate a first reactant upon the absorption of at least one photon of a particular wavelength of light. The first reactant may be effective to render the resin soluble or insoluble in a photoresist developer. The photoinhibitor may be effective to generate a second reactant upon the absorption of at least one photon of the particular wavelength of light. The second reactant may be effective to inhibit the first reactant.Type: GrantFiled: November 3, 2010Date of Patent: November 12, 2013Assignee: Empire Technology Development, LLCInventor: Seth Miller
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Patent number: 8288073Abstract: This invention provides a method for resist under layer film formation, which can form a resist under layer film which can function as an anti-reflection film, is excellent in pattern transfer properties and etching resistance, and does not cause bending of a pattern even in the transfer of a fined pattern, and a composition for the resist under layer film for use in the method, and a method for pattern formation. The method for resist under layer film formation comprises the steps of coating a composition for resist under layer film formation (for example, a composition comprising a compound having a phenolic hydroxyl group, a solvent, and an accelerator) onto a substrate to be processed, and treating the formed coating film under an oxidizing atmosphere having an oxygen concentration of not less than 1% by volume and a temperature of 300° C. or higher to form a resist under layer film.Type: GrantFiled: September 18, 2007Date of Patent: October 16, 2012Assignee: JSR CorporationInventors: Yousuke Konno, Nakaatsu Yoshimura, Fumihiro Toyokawa, Hikaru Sugita
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Patent number: 7713677Abstract: A photoresist composition capable of forming a high resolution pattern without an additional heating process includes an alkali-soluble phenol polymer in an amount of 10 to 70 parts by weight, including at least one unit of Formula 1, a photo-acid generator in an amount of 0.5 to 10 parts by weight, a dissolution inhibitor in an amount of 5 to 50 parts by weight, including at least one unit of Formula 2, and a solvent in an amount of 10 to 90 parts by weight, wherein the amounts of the foregoing components is based on a total of 100 parts by weight of alkali-soluble phenol polymer, photo-acid generator, dissolution inhibitor, and solvent, and wherein Formulas 1 and 2 have the structures: wherein R is a methyl group, wherein R1, R2 and R3 are the same or different and are hydrogen or t-butyl vinyl ether protective groups.Type: GrantFiled: November 22, 2006Date of Patent: May 11, 2010Assignee: Samsung Electronics Co., Ltd.Inventors: Hi Kuk Lee, Byung Uk Kim, Hyoc Min Youn, Joo Pyo Yun, Woo Seok Jeon
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Patent number: 7531288Abstract: A photosensitive lithographic printing plate comprising: a hydrophilic support; and a photosensitive layer containing a polymerization initiator, a chain transfer agent, a compound having an ethylenically unsaturated double bond and a polymer binder having a crosslinkable group in a side chain, wherein the chain transfer agent is a thiol compound represented by the following formula (I): in which R represents an alkyl group which may have a substituent or an aryl group which may have a substituent; and A represents an atomic group necessary for forming a 5-membered or 6-membered hetero ring containing a carbon atom together with the N?C—N linkage, and A may have a substituent.Type: GrantFiled: September 26, 2005Date of Patent: May 12, 2009Assignee: FUJIFILM CorporationInventors: Keisuke Arimura, Takahiro Goto
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Patent number: 7524606Abstract: The present invention relates to a photoresist composition suitable for image-wise exposure and development as a positive photoresist comprising a positive photoresist composition and an inorganic particle material having an average particle size equal or greater than 10 nanometers, wherein the thickness of the photoresist coating film is greater than 5 microns. The positive photoresist composition can be selected from (1) a composition comprising (i) a film-forming resin having acid labile groups, and (ii) a photoacid generator, or (2) a composition comprising (i) a film-forming novolak resin, and (ii) a photoactive compound, or (3) a composition comprising (i) a film-forming resin, (ii) a photoacid generator, and (iii) a dissolution inhibitor.Type: GrantFiled: April 11, 2005Date of Patent: April 28, 2009Assignee: AZ Electronic Materials USA Corp.Inventors: Chunwei Chen, Ping-Hung Lu, Hong Zhuang, Mark Neisser
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Patent number: 7442489Abstract: In a photoresist composition for a semiconductor manufacturing process and a method of forming a photoresist pattern using the photoresist composition, the photoresist composition includes an organic dispersing agent for dispersing acid (H+). The photoresist film may have enough spaces among photosensitive polymers so that acid may be dispersed sufficiently in an exposure process. Thus, a photoresist pattern may be easily formed in a defocus region. Defects in a semiconductor device may be reduced and a productivity of the semiconductor manufacturing process may be enhanced.Type: GrantFiled: January 17, 2006Date of Patent: October 28, 2008Assignee: Samsung Electronics Co., Ltd.Inventors: Boo-Deuk Kim, Jin-A Ryu, Jae-Ho Kim, Young-Ho Kim, Kyoung-Mi Kim
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Patent number: 7407734Abstract: A resist composition and a method of forming a resist pattern that enable contamination within the exposure apparatus to be prevented in lithography processes using an electron beam or EUV (extreme ultraviolet light). In this method, an organic solvent containing, as the principal component, one or more compounds selected from a group consisting of propylene glycol monomethyl ether (PGME), methyl amyl ketone (MAK), butyl acetate (BuOAc), and 3-methyl methoxy propionate (MMP) is used as the resist solvent.Type: GrantFiled: October 20, 2004Date of Patent: August 5, 2008Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Takeo Watanabe, Hideo Hada, Hiroo Kinoshita
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Patent number: 7285372Abstract: Radiation-sensitive element comprising (a) a substrate with at least one hydrophilic surface and (b) a radiation-sensitive coating on at least one hydrophilic surface of the substrate, wherein the coating comprises: (i) at least one free-radical polymerizable monomer and/or oligomer and/or polymer with at least one ethylenically unsaturated group each, (ii) at least one absorber selected from photoinitiators and sensitizers, which is capable of absorbing radiation of a wavelength in the range of 250 to 1,200 nm and (iii) at least one stabilizer comprising in its molecule at least one group capable of inhibiting free-radical polymerization, and at least one other group capable of sorption at the hydrophilic surface of the substrate.Type: GrantFiled: November 28, 2003Date of Patent: October 23, 2007Assignee: Kodak Graphic Communications GmbHInventors: Harald Baumann, Michael Flugel, Udo Dwars, Eduard Kottmair
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Patent number: 7232646Abstract: The invention relates to a biocompatible, low-viscous, radiation curable formulation, particularly for use in stereolithography, for use in medical technology, in particular, for producing earpieces, containing: a) 55-95% by weight of a monomeric or oligomeric dimethacrylate based on bisphenol A or bisphenol F; b) 0-20% by weight of a urethane methacrylate having a functionality of n<4 and a viscosity<15 Pa s; c) 2-15% by weight of a monomeric aliphatic or cycloaliphatic dimethacrylate having a viscosity<5 Pa s; d) 0-15% by weight of a monofunctional methacrylate having a viscosity<3 Pa s; e) 0.5-6% by weight of a photoinitiator or a combination of a number of photoinitiators whose absorption is located within the wavelength range of the laser beam used; f) 0.Type: GrantFiled: June 17, 2004Date of Patent: June 19, 2007Assignee: Dreve-Otoplastik GmbHInventors: Martin Klare, Reiner Altmann, Michael Kutschinski, Georgia Meissner, Thomas Veit
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Patent number: 7192681Abstract: A positive photosensitive composition comprising (A) an acid generator that generates an acid upon irradiation of an actinic ray or radiation, (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, and (C) a specific basic compound.Type: GrantFiled: July 3, 2002Date of Patent: March 20, 2007Assignee: Fuji Photo Film Co., Ltd.Inventor: Toru Fujimori
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Patent number: 7060414Abstract: A radiation-sensitive resin composition comprising (A) a photoacid generator such as 2,4,6-trimethylphenyldiphenylsulfonium 2,4-difluorobenzenesulfonate or 2,4,6-trimethylphenyldiphenylsulfonium 4-trifluoromethylbenzenesulfonate and (B) a resin having an acetal structure typified by a poly(p-hydroxystyrene) resin in which a part of hydrogen atoms of phenolic hydroxyl groups have been replaced by 1-ethoxyethyl groups, 1-ethoxyethyl groups and t-butoxycarbonyl groups, or 1-ethoxyethyl groups and t-butyl groups. The resin composition is sensitive to deep ultraviolet rays and charged particles such as electron beams, exhibits excellent resolution performance and pattern shape-forming capability, and suppresses a nano-edge roughness phenomenon to a minimal extent.Type: GrantFiled: March 16, 2005Date of Patent: June 13, 2006Assignee: JSR CorporationInventors: Aki Suzuki, Makoto Murata, Hiromichi Hara, Eiichi Kobayashi
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Patent number: 6977131Abstract: A radiation-sensitive patterning composition comprising: (1) at least one acid generating compound selected from the group of compounds of formulae (I) or (II): wherein R1, R2, R3, R4, R5, and R6, are individually selected from the group consisting of a hydrogen atom, nitro group, hydroxyl group, a carbonyl group, a halogen atom, a cyano group and an unsubstituted or substituted alkyl group, an unsubstituted or substituted cycloalkyl group; an unsubstituted or substituted alkoxy group, or an unsubstituted or substituted aryl group; wherein X+ represents an onium ion selected from the group consisting of diazonium, iodonium, sulfonium, phosphonium, bromonium, chloronium, oxysulfoxonium, oxysulfonium, sulfoxonium, selenium, tellurium and arsenium; and wherein n is an integer from 4 to 100; (2) at least one cross-linking agent cross-linkable by an acid; (3) at least one polymer compound capable of reacting with the cross-linking agent; and (4) at least one infrared absorbing compound.Type: GrantFiled: May 30, 2002Date of Patent: December 20, 2005Assignee: Kodak Polychrome Graphics LLCInventor: Ting Tao
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Patent number: 6929896Abstract: A chemically amplified photoresist composition comprising, (a) a compound which cures upon the action of an acid or a compound whose solubility is increased upon the action of an acid; and (b) as photosensitive acid donor, at least one compound of the formula Ia, Ib, Ic, IIb or IIc wherein R1 is for example C1-C5alkyl, C3-C30cycloalkyl, C1-C5haloalkyl, C2-C12alkenyl, C4-C8cycloalkenyl, C6-C12bicycloalkenyl, phenyl, naphthyl, anthracyl, phenanthryl, or is a heteroaryl radical; all of which are unsubstituted or substituted; optionally some of the substituents form 5- or 6-membered rings with further substituents on the phenyl, naphthyl, anthracyl, phenanthryl, or heteroaryl ring or with one of the carbon atoms of the phenyl, naphtyl, anthracyl, phenanthryl, or heteroaryl ring; R?1 is for example C1-C12alkylene, C3-C30cycloalkylene, phenylene, naphtylene, diphenylene, or oxydiphenylene, wherein these radicals are unsubstituted or substituted; A and B for example are a direct bond; Ar1 and Ar2 independently of eaType: GrantFiled: November 26, 2001Date of Patent: August 16, 2005Assignee: Ciba Specialty Chemicals CorporationInventors: Hitoshi Yamato, Toshikag Asakura, Akira Matsumoto, Masaki Ohwa
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Patent number: 6919159Abstract: The present invention provides a photopolymerizable composition, which is highly sensitive to visible light rays to IR rays and has an excellent raw storage property, and a recording material capable of carrying out highly sensitive image recording and having an excellent raw storage property and humidity dependency. Namely, the invention provides a photopolymerizable composition containing at least a polymerizable compound having an ethylenic unsaturated bond, a photoradical generating agent, and a thiol compound represented by the following general formula (I) and a recording material using the photopolymerizable composition: [R represents an alkyl or an aryl, either of which may have substituents; A represents an atom group forming a 5-member or 6-member heteroring having an N?C—N portion and carbon atoms and A may further have a substituent group.].Type: GrantFiled: October 7, 2002Date of Patent: July 19, 2005Assignee: Fuji Photo Film Co., Ltd.Inventors: Hirotaka Matsumoto, Shintaro Washizu, Kazunori Nigorikawa
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Patent number: 6899989Abstract: A radiation-sensitive resin composition comprising (A) a photoacid generator such as 2,4,6-trimethylphenyldiphenylsulfonium 2,4-difluorobenzenesulfonate or 2,4,6-trimethylphenyldiphenylsulfonium 4-trifluoromethylbenzenesulfonate and (B) a resin having an acetal structure typified by a poly(p-hydroxystyrene) resin in which a part of hydrogen atoms of phenolic hydroxyl groups have been replaced by 1-ethoxyethyl groups, 1-ethoxyethyl groups and t-butoxycarbonyl groups, or 1-ethoxyethyl groups and t-butyl groups. The resin composition is sensitive to deep ultraviolet rays and charged particles such as electron beams, exhibits excellent resolution performance and pattern shape-forming capability, and suppresses a nano-edge roughness phenomenon to a minimal extent.Type: GrantFiled: November 16, 2001Date of Patent: May 31, 2005Assignee: JSR CorporationInventors: Aki Suzuki, Makoto Murata, Hiromichi Hara, Eiichi Kobayashi
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Patent number: 6869748Abstract: Resist compositions comprising as the base resin a polymer using an alkoxyalkyl (meth)acrylate as a reactive group which is decomposable under the action of an acid to increase solubility in alkali have advantages including a practical level of shelf stability, a significantly enhanced contrast of alkali dissolution rate before and after exposure, a high sensitivity, and a high resolution over a wide baking temperature range. The compositions are best suited as a chemically amplified positive resist material for micropatterning in the manufacture of VLSI.Type: GrantFiled: July 3, 2003Date of Patent: March 22, 2005Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Takanobu Takeda, Osamu Watanabe
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Patent number: 6864040Abstract: The present invention relates to IR-sensitive compositions containing an initator system comprising: (a) at least one compound capable of absorbing IR radiation selected from triarylamine dyes, thiazolium dyes, indolium dyes, oxazolium dyes, cyanine dyes, polyaniline dyes, polypyrrole dyes, polythiophene dyes and phthalocyanine pigments (b) at least one compound capable of producing radicals selected from polyhaloalkyl-substituted compounds (c) at least one polycarboxylic acid represented by the following formula I wherein Y is selected from the group consisting of O, S and NR7, each of R4, R5 and R6 is independently selected from the group consisting of hydrogen, C1-C4 alkyl, aryl which is optionally substituted, —COOH and NR8CH2COOH, R7 is selected from the group consisting of hydrogen, C1-C6 alkyl, —CH2CH2OH, and C1-C5 alkyl substituted with -COOH, R8 is selected from the group consisting of —CH2COOH, —CH2OH and —(CH2)2N(CH2COOH)2 and r is 0, 1, 2 or 3 with the proviso that at least one of R4, R5, RType: GrantFiled: April 11, 2001Date of Patent: March 8, 2005Assignee: Kodak Polychrome Graphics LLCInventors: Ursula Müller, Tobias Wittig, Hans-Joachim Timpe
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Patent number: 6815143Abstract: Provided are a PED-stabilizer-containing resist material having high sensitivity and high resolution, and sufficient PED stability; and a pattern forming method using the resist material. More specifically, the resist material contains at least one compound selected from thiol derivatives, disulfide derivatives and thiolsulfonate derivatives. This resist material may further contain a dissolution inhibitor and/or surfactant. The pattern forming method comprises steps of applying the resist material to a substrate; after a heat treatment, exposing the substrate to a high energy beam or electron beam through a photomask; and after an optional heat treatment, developing the resist material with a developer.Type: GrantFiled: January 18, 2002Date of Patent: November 9, 2004Assignee: Shin-Etsu Chemical Co., Ltd.Inventor: Satoshi Watanabe
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Publication number: 20040067431Abstract: A photoreactive composition comprises (a) at least one reactive species that is capable of undergoing an acid- or radical-initiated chemical reaction; and (b) a photoinitiator system comprising photochemically-effective amounts of (1) at least one type of semiconductor nanoparticle quantum dot that has at least one electronic excited state that is accessible by absorption of two or more photons, and (2) a composition, different from said reactive species, that is capable of interacting with the excited state of the semiconductor nanoparticle quantum dot to form at least one reaction-initiating species.Type: ApplicationFiled: October 2, 2002Publication date: April 8, 2004Applicant: 3M Innovative Properties CompanyInventors: David S. Arney, Catherine A. Leatherdale, Manoj Nirmal
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Publication number: 20040058279Abstract: This invention provides a pattern formation material for electron beam lithography, which contains an alkali-soluble resin, a photoacid generator, and dissolution inhibiting groups, and also provides a pattern formation method and exposure mask fabrication method using the material. As the dissolution inhibiting groups, this invention uses a first dissolution inhibiting group which increases the sensitivity of the pattern formation material when the material is left to stand in a vacuum after an electron beam irradiation, and a second dissolution inhibiting group which decreases the sensitivity under the same condition. In this invention, the ratio of the first dissolution inhibiting group to the second dissolution inhibiting group is so adjusted that the size of an alkali-soluble portion, which is made soluble in an alkali solution by an electron beam irradiation, is substantially held constant independently of the standing time in a vacuum.Type: ApplicationFiled: September 22, 2003Publication date: March 25, 2004Applicant: Kabushiki Kaisha ToshibaInventors: Masamitsu Itoh, Takehiro Kondoh
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Publication number: 20040053158Abstract: A chemically amplified photoresist composition comprising, (a) a compound which cures upon the action of an acid or a compound whose solubility is increased upon the action of an acid; and (b) as photosensitive acid donor, at least one compound of the formula Ia, Ib, Ic, IIb or IIc wherein R1 is for example C1-Calkyl, C3-C30cycloalkyl, C1-C5haloalkyl, C2-C12alkenyl, C4-C8cycloalkenyl, C6-C12bicycloalkenyl, phenyl, naphthyl, anthracyl, phenanthryl, or is a heteroaryl radical; all of which are unsubstituted or substituted; optionally some of the substituents form 5- or 6-membered rings with further substituents on the phenyl, naphthyl, anthracyl, phenanthryl, or heteroaryl ring or with one of the carbon atoms of the phenyl, naphtyl, anthracyl, phenanthryl, or heteroaryl ring; R′1 is for example C1-C12alkylene, C3-C30cycloalkylene, phenylene, naphtylene, diphenylene, or oxydiphenylene, wherein these radicals are unsubstituted or substituted; A and B for example are a direct bond; Ar1 and Ar2 independentlyType: ApplicationFiled: May 21, 2003Publication date: March 18, 2004Inventors: Hitoshi Yamato, Toshikage Asakura, Akira Matsumoto, Masaki Ohwa
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Publication number: 20040023153Abstract: Resist compositions comprising as the base resin a polymer using an alkoxyalkyl (meth)acrylate as a reactive group which is decomposable under the action of an acid to increase solubility in alkali have advantages including a practical level of shelf stability, a significantly enhanced contrast of alkali dissolution rate before and after exposure, a high sensitivity, and a high resolution over a wide baking temperature range. The compositions are best suited as a chemically amplified positive resist material for micropatterning in the manufacture of VLSI.Type: ApplicationFiled: July 3, 2003Publication date: February 5, 2004Inventors: Takanobu Takeda, Osamu Watanabe
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Publication number: 20040013977Abstract: A liquid radiation-curable composition that comprisesType: ApplicationFiled: January 7, 2003Publication date: January 22, 2004Applicant: 3D Systems, Inc.Inventor: Bettina Steinmann
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Publication number: 20030129523Abstract: The present invention provides a photopolymerizable composition, which is highly sensitive to visible light rays to IR rays and has an excellent raw storage property, and a recording material capable of carrying out highly sensitive image recording and having an excellent raw storage property and humidity dependency.Type: ApplicationFiled: October 7, 2002Publication date: July 10, 2003Inventors: Hirotaka Matsumoto, Shintaro Washizu, Kazunori Nigorikawa
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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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Patent number: 6562543Abstract: A stabilizer for thermally stabilizing an organic borate salt represented by formula (1) is disclosed, comprising a compound having one or two nitrogen-containing 5- or 6-membered heterocyclic ring having a double bond within the ring, a compound having a primary, secondary or tertiary amino group, or a compound having a thiol group. Also disclosed are a photosensitive composition comprising the stabilizer, an organic borate salt and if desired, a sensitizing dye or further a bisimidazole compound; a polymerizable composition comprising the photosensitive composition having added thereto at least one monomer having one or more ethylenically unsaturated bond and if desired, a high molecular polymer or further a pigment; and a colored pattern formed by using the polymerizable composition.Type: GrantFiled: January 22, 2001Date of Patent: May 13, 2003Assignee: Showa Denko K.K.Inventors: Tomonari Ogata, Tsuyoshi Katoh, Tomoe Uematsu, Norihide Arai, Tomoki Okano
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Publication number: 20010046643Abstract: A stabilizer for thermally stabilizing an organic borate salt represented by formula (1) is disclosed, comprising a compound having one or two nitrogen-containing 5- or 6-membered heterocyclic ring having a double bond within the ring, a compound having a primary, secondary or tertiary amino group, or a compound having a thiol group. Also disclosed are a photosensitive composition comprising the stabilizer, an organic borate salt and if desired, a sensitizing dye or further a bisimidazole compound; a polymerizable composition comprising the photosensitive composition having added thereto at least one monomer having one or more ethylenically unsaturated bond and if desired, a high molecular polymer or further a pigment; and a colored pattern formed by using the polymerizable composition.Type: ApplicationFiled: January 22, 2001Publication date: November 29, 2001Inventors: Tomonari Ogata, Tsuyoshi Katoh, Tomoe Uematsu, Norihide Arai, Tomoki Okano
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Patent number: 6306553Abstract: A photosensitive composition comprising: an acid-decomposable compound having at least one substituent which is decomposed by an acid, forming a product which reacts with alkali solution and forms —COO− or —SO3−; and a compound which generates an acid when exposed to a chemical radiation. If necessary, the composition further comprises an alkali-soluble polymer. The acid-decomposable compound is one which is represented by the following formula (1), and the alkali-soluble polymer has a softening point of 150° C. or more and an average molecular weight of 3000 to 8000. When used as photoresist, the composition can form a fine resist pattern.Type: GrantFiled: June 7, 1995Date of Patent: October 23, 2001Assignee: Kabushiki Kaisha ToshibaInventors: Naoko Kihara, Fumihiko Yuasa, Tohru Ushirogouchi, Tsukasa Tada, Osamu Sasaki, Takuya Naito, Satoshi Saito
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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: 6238842Abstract: An object of the present invention is to provide a positive photosensitive composition suitable for use with an exposure light having a wavelength of 250 nm or shorter, especially 220 nm or shorter.Type: GrantFiled: March 11, 1999Date of Patent: May 29, 2001Assignee: Fuji Photo Film Co., Ltd.Inventors: Kenichiro Sato, Toshiaki Aoai
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Patent number: 6162579Abstract: The invention provides improved high contrast, photopolymerizable compositions suitable for producing high contrast waveguides. The high contrast, photopolymerizable compositions of this invention include a nitrone compound component. The photosensitive composition is an admixture of a free radical polymerizable acrylate or methacrylate component having at least two ethylenically unsaturated groups, a photoinitiator, and a nitrone compound.Type: GrantFiled: April 19, 1996Date of Patent: December 19, 2000Assignee: Corning IncorporatedInventors: Kelly M. T. Stengel, Lawrence W. Shacklette, Louay Eldada, James T. Yardley, Chengzeng Xu, Scott M. Zimmerman, Keith A. Horn
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Patent number: 6103450Abstract: A photosensitive polymer, a dissolution inhibitor, and a chemically amplified photoresist composition containing the photosensitive polymer and the dissolution inhibitor are provided. The photosensitive polymer is a copolymer polymerized with 5-norbornene-2-methanol derivative monomer having a C.sub.1 to C.sub.20 aliphatic hydrocarbon as a side chain, and a maleic anhydride monomer. The dissolution inhibitor is a tricyclodecane derivative or a sarsasapogenin derivative, each having an acid-labile group as a functional group. The chemically amplified photoresist composition containing the photosensitive polymer and/or dissolution inhibitor has a strong resistance to etching and excellent adherence to underlying layer.Type: GrantFiled: March 26, 1999Date of Patent: August 15, 2000Assignee: Samsung Electronics Co., Ltd.Inventor: Sang-jun Choi
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Patent number: 6030746Abstract: Di- or triphenyl monoterpene hydrocarbon derivatives of formula (1) are novel. ##STR1## X is a di- or trivalent monoterpene hydrocarbon group, R.sup.1 to R.sup.3 are hydrogen or an alkyl, alkoxy, alkoxyalkyl, alkenyl or aryl group, R.sup.4 is hydrogen or an acid labile group, at least one R.sup.4 being an acid labile group, letter n is an integer of 1-5, j, k and m are integers of 0-4, n+j+k+m=5, and p is 2 or 3. When used as a dissolution rate regulator, the compound of formula (1) exerts remarkably enhanced dissolution inhibitory effect and minimized light absorption in the deep-UV region. A chemically amplified positive resist composition having the compound of formula (1) blended therein is highly sensitive to actinic radiation such as deep-UV radiation, electron beam and X-ray, especially KrF excimer laser light, and has improved sensitivity, resolution and plasma etching resistance.Type: GrantFiled: April 1, 1997Date of Patent: February 29, 2000Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Takeshi Nagata, Satoshi Watanabe, Tsunehiro Nishi, Jun Hatakeyama, Shigehiro Nagura, Toshinobu Ishihara
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Patent number: 5945250Abstract: A photosensitive composition containing a sulfonium or iodonium salt resin having a specific repeating structural units has good solubility in solvents and high photosensitivity, are capable of giving an excellent resist pattern, and change little with time after exposure.Type: GrantFiled: June 4, 1997Date of Patent: August 31, 1999Assignee: Fuji Photo Film Co., Ltd.Inventors: Toshiaki Aoai, Kenichiro Sato, Kunihiko Kodama
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Patent number: 5939238Abstract: The invention provides a negative-acting photoimageable composition comprising A) between about 30 and about 80 wt % based on total weight of A) plus B) of a binder polymer having acid functionality sufficient to render said photoimageable composition developable in alkaline aqueous solution, B) between about 20 and about 70 wt % based on total weight of A) plus B) of an addition-polymerizeable, non-gaseous .alpha.,.beta.-ethylenically unsaturated compound(s) capable of forming a high polymer by free-radical initiated chain-propagating addition polymerization, at least about 50 mole percent of the .alpha.,.beta.-ethylenically unsaturated moieties of B) being methacrylic moieties, and C) between about 0.1 and about 20 wt % based on total weight of A) plus B) of a photoinitiator chemical system, the photoinitiator chemical system comprising between about 0.005 and about 3 wt % relative to total weight of A) plus B) of triphenyphosphine and between about 0.Type: GrantFiled: June 2, 1998Date of Patent: August 17, 1999Assignee: Morton International, Inc.Inventors: Robert Barr, Daniel E. Lundy, Eiji Kosaka, Shigeru Murakami
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Patent number: 5912106Abstract: The instant invention pertains to a method of improving the quality and resolution of photoimages by incorporating into the photocurable resin composition to be used a selected amount of a polymerization inhibitor so that photopolymerization of the photocurable resin is inhibited in those areas not directly impinged by light.Type: GrantFiled: March 12, 1997Date of Patent: June 15, 1999Assignee: Ciba Specialty Chemicals CorporationInventors: Chia-Hu Chang, Andrew Mar, Thai Hong Nguyen, Harry Joseph Evers, Hugh Stephen Laver
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Patent number: 5773194Abstract: A light sensitive composition comprising (a) a vinyl type polymer having a unit represented by the following Formula (1) and a carboxyl group, (b) a monomer, oligomer or polymer containing at least one polymerizable double bond in its molecule, (c) a photopolymerization initiator and (d) a polymerization inhibitor capable of trapping a radical, ##STR1##Type: GrantFiled: August 29, 1996Date of Patent: June 30, 1998Assignee: Konica CorporationInventors: Ryoji Hattori, Tatsuichi Maehashi, Takaaki Kuroki, Sota Kawakami
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Patent number: 5698373Abstract: The present invention relates to a photosensitive relief or intaglio printing plate comprising a base and a photocurable photosensitive layer formed on the base, the photocurable photosensitive layer containing a dye precursor which forms a dye upon irradiation of actinic light. A relief (convex) pattern or a concave pattern can be recognized by coloring, thereby facilitating the printing plate inspecting work. The developing solution used is not colored or contaminated.Type: GrantFiled: August 2, 1994Date of Patent: December 16, 1997Assignee: Toray Industries, IncorporatedInventors: Junichi Fujikawa, Takao Kinashi, Shigetora Kashio, Yasuko Yokoyama
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Patent number: 5681634Abstract: The disk-shaped optical information medium of this invention includes: a first substrate having a center hole; a second substrate having a center hole; and a radiation curable resin interposed between the first and second substrates for bonding together the first and second substrates, wherein the optical information medium further includes a stopper for preventing the radiation curable resin from protruding into the center holes of the substrates, and a space between the first and second substrates of at least a half of a clamp region for clamping the optical information medium is filled with the resin.Type: GrantFiled: February 9, 1996Date of Patent: October 28, 1997Assignee: Matsushita Electric Industrial Co., Ltd.Inventors: Hisaki Miyamoto, Michiyoshi Nagashima, Kiyoshi Inoue, Sakae Noda
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Patent number: 5580695Abstract: A chemically amplified resist comprising an alkali-soluble resin or a resin having at least one acid-dissociable group which is alkali-insoluble or -sprairingly soluble but becomes alkali-soluble upon dissociation of said acid dissociable group due to an acid; a radiation-sensitive, acid-generating agent; and an optional component in which resist, the radiation-sensitive, acid-generating agent generates an acid upon irradiation with a radiation in the irradiated portion and the solubility of the resin component and optional component in a developing solution is varied in the irradiated portion by a chemical reaction caused by the catalytic action of the acid, whereby a pattern is formed, characterized in that a compound having a nitrogen-containing basic group is contained in the resist.Type: GrantFiled: November 10, 1994Date of Patent: December 3, 1996Assignee: Japan Synthetic Rubber Co., Ltd.Inventors: Makoto Murata, Takao Miura, Yoshiji Yumoto, Toshiyuki Ota, Eiichi Kobayashi
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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: 5512417Abstract: A positive resist composition comprising a poly(p-hydroxystyrene) as matrix resin which is synthesized by an anionic polymerization method and has a weight average molecular weight of from 8,000 to 20,000, bis(p-t-butoxycarbonylmethyl)thymolphthalein as dissolution inhibitor, bis(p-t-butylphenyl)iodonium triflate as acid generator; a compound which contains one amino group and one carboxyl group to function as acid deactivator and propylene glycol monomethyl ether acetate as organic solvent.Type: GrantFiled: February 14, 1995Date of Patent: April 30, 1996Assignees: Shin-Etsu Chemical Co., Ltd., Nippon Telegraph and Telephone Corp.Inventors: Hiroshi Ban, Akinobu Tanaka, Fujio Yagihasi, Jun Watanabe, Minoru Takamizawa
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Patent number: 5403698Abstract: A negative type photosensitive electrodepositing resin composition comprising (a) a polymer obtained by neutralizing a copolymer of acrylic or methacrylic acid and having an acid number of 20 to 300 with a basic organic compound, (b) a non-water-soluble monomer having two or more photopolymerizable unsaturated bonds in the molecule, (c) a non-water-soluble photoinitiator, and (d) a benzotriazole derivative having one or more carboxyl groups, is effective for giving electrodeposited films with a low voltage or low electric current in a short time, and usable for forming resist patterns with high degree of resolution.Type: GrantFiled: October 11, 1991Date of Patent: April 4, 1995Assignees: Hitachi Chemical Company, Ltd., Dai Nippon Toryo Co., Ltd.Inventors: Sigeo Tachiki, Masahiko Hiro, Toshihiko Akahori, Takuro Kato, Hajime Kakumaru, Yoshitaka Minami, Yuhji Yamazaki, Toshiya Takahashi, Toshihiko Shiotani, Yoshihisa Nagashima
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Patent number: 5346805Abstract: A photopolymerizable composition comprises a polymerizable compound having at least one ethylenically unsaturated double bond and a photopolymerization initiator, wherein the photopolymerization initiator comprises an onium compound and an acridine derivative represented by the following general formula (I): ##STR1## wherein R.sup.1 represents an unsubstituted or substituted phenyl, alkyl or alkoxy group. The composition has high sensitivity to actinic rays over a wide range of wavelength extending from ultraviolet to visible region and thus can be used for preparing a lithographic printing plate, a resin-letterpress plate, a resist or photomask for making a printed board, a monochromatic and colored sheet for transfer or color-development and a color-developing sheet.Type: GrantFiled: September 17, 1993Date of Patent: September 13, 1994Assignee: Fuji Photo Film Co., Ltd.Inventors: Syunichi Kondo, Akira Umehara
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Patent number: 5332648Abstract: A photosensitive composition comprising: an acid-decomposable compound having at least one substituent which is decomposed by an acid, forming a product which reacts with alkali solution and forms --COO.sup.- or --SO.sub.3.sup.- ; and a compound which generates an acid when exposed to a chemical radiation. If necessary, the composition further comprises an alkali-soluble polymer. The acid-decomposable compound is one which is represented by the following formula (1), and the alkali-soluble polymer has a softening point of 150.degree. C. or more and an average molecular weight of 3000 to 8000. When used as photoresist, the composition can form a fine resist pattern. ##STR1## where R.sub.1 and R.sub.2 are either the same or different, each of which represents at least one selected from the group consisting of hydrogen, halogen atom, cyano group, nitro group, silyl group, and monovalent organic group; X represents >C.dbd.O or --SO.sub.2 --; Y represents a divalent organic group; R.sub.1 and R.sub.Type: GrantFiled: December 27, 1991Date of Patent: July 26, 1994Assignee: Kabushiki Kaisha ToshibaInventors: Naoko Kihara, Fumihiko Yuasa, Tohru Ushirogouchi, Tsukasa Tada, Osamu Sasaki, Takuya Naito, Satoshi Saito
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Method and composition for obtaining image reversal in epoxy formulations based upon photoinhibition
Patent number: 5266444Abstract: A method and composition are shown for producing a positive-acting photoimagible epoxy resin. In addition to the epoxy resin, the compositions include a dual component cross-linking system which combines a basic curing agent with an onium or arylonium salt. The onium or arylonium salt produces a protic acid upon exposure to irradiation causing a reaction with the basic curing agent which renders the agent ineffective as an epoxy curing agent during subsequent heating. During a subsequent bake operation, only the unexposed regions of the epoxy will cross-link. As a result, the exposed areas wash away, leaving only the cured reverse image.Type: GrantFiled: September 10, 1992Date of Patent: November 30, 1993Assignee: International Business Machines CorporationInventors: Burton J. Carpenter, Jr., Joseph LaTorre, Michael G. McMaster, Logan L. Simpson -
Patent number: 5254437Abstract: Disclosed is a photosensitive resin plate which effectively prevents dot gain by covering the photosensitive resin layer with a specific matte layer. The photosensitive resin plate comprises a substrate, a photosensitive resin layer formed on the substrate and a resin matte layer formed on the photosensitive resin layer, wherein the resin matte layer contains a polymerization inhibiting material.Type: GrantFiled: February 8, 1993Date of Patent: October 19, 1993Assignee: Nippon Paint Co., Ltd.Inventors: Koichi Ueda, Katsuji Konishi, Kazunori Kanda
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Patent number: 5230981Abstract: An image recording process is disclosed. The process comprises the steps of: imagewise exposing silver halide to light to form a latent image of the silver halide; developing the formed latent image of the silver halide with a reducing agent; and conducting substantially uniform light exposure in the presence of a photopolymerization initiator and an ethylenically unsaturated polymerizable compound to form a polymer image. According to the present invention, the reducing agent forms an oxidation product having a function as a polymerization inhibitor after the development. Thus a polymer image is formed within the area where the oxidation product of the reducing agent has not been formed. The reducing agent has the following formula [I]: ##STR1## in which R.sup.1 is an alkyl group, an aryl group or a heterocyclic group; R.sup.2 is an organic group which is attached to the benzene ring by a hetero-atom having a lone pair of electrons; R.sup.Type: GrantFiled: February 21, 1990Date of Patent: July 27, 1993Assignee: Fuji Photo Film Co., Ltd.Inventors: Naoki Saito, Makoto Yamada
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Patent number: 5221595Abstract: A photopolymerizable mixture is disclosed that contains a polymer binder, a polymerizable compound having at least one terminal ethylene double bond and a boiling point above 100.degree. C. at normal pressure, a hexaarylbisimidazole and a 1,3-diarylpyrazoline or a 1-aryl-3-aralkenyl-pyrazoline. The mixture is suitable for the preparation of printing plates and photoresists and is distinguished by high photosensitivity and low sensitivity towards acid solutions.Type: GrantFiled: March 27, 1991Date of Patent: June 22, 1993Assignee: Hoechst AktiengesellschaftInventors: Juergen Lingnau, Hans-Dieter Frommeld