Polymer Of Unsaturated Acid Or Ester Patents (Class 430/910)
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Patent number: 7202009Abstract: This invention relates to resins and photoresist compositions that comprise such resins. Preferred polymers of the invention comprise adjacent saturated carbon atoms, either integral or pendant to the polymer backbone, that have a substantially gauche conformation. Polymers of the invention are particularly useful as a resin binder component of chemically-amplified positive-acting resists that can be effectively imaged at short wavelengths such as sub-200 nm and preferably about 157 nm. In such short-wavelength imaging applications, polymers of the invention that have a population of dihedral angles of adjacent saturated carbon atoms that are enriched in substantially gauche conformations can provide reduced undesired absorbance of the high energy exposure radiation.Type: GrantFiled: September 8, 2001Date of Patent: April 10, 2007Assignee: Shipley Company, L.L.C.Inventors: Peter Trefonas, III, Gary N. Taylor, Charles R. Szmanda
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Patent number: 7202010Abstract: A chemical amplification type positive resist composition, which can reduce cost steeply without significantly decreasing basic abilities, is provided, and the chemical amplification type positive resist composition includes (A) a resin having a polymerization unit derived from p-hydroxystyrene and a polymerization unit of the formula (1) or formula (2) which is insoluble or poorly soluble itself in an alkali aqueous solution but becomes soluble in an alkali aqueous solution by the action of an acid, (B) a resin obtained by protecting a portion of the hydroxyl groups in poly(p-hydroxystyrene) with a protective group not dissociating by the action of an acid or a resin obtained by substituting a portion of the hydroxyl groups in poly(p-hydroxystyrene) with hydrogen, and (C) an acid generating agent.Type: GrantFiled: September 26, 2002Date of Patent: April 10, 2007Assignee: Sumitomo Chemical Company LimitedInventors: Airi Yamada, Masumi Suetsugu, Yasunori Uetani
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Patent number: 7198884Abstract: The invention relates to a process for preparing a dry film resist by forming a photocurable resin composition onto a support film with a thickness of 1 to 50 ?m and optionally laminate a protective film onto the photocurable composition layer to obtain a dry film resist; whereby the photocurable resin is formed from a homogeneous mixture comprising (a) from 20–90 wt % of an alkaline soluble binder oligomer or polymer; (b) from 5 to 60 wt % of one or more photopolymerizable monomers which are compatible with the oligomers and polymers of component (a); (c) from 0.01 to 20% by weight of one or more photoinitiators; (d) from 0 to 20% by weight of additives and/or assistants; and (e) from 0.Type: GrantFiled: July 1, 2003Date of Patent: April 3, 2007Assignee: Ciba Specialty Chemicals Corp.Inventors: Hidetaka Oka, Masaki Ohwa, James Philip Taylor
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Patent number: 7192688Abstract: A composition comprising a polymer according to Structure 1 wherein R is H, Me, Et or C6H5; R? is H or Me; R? is H or Me; n=1 to 100; and Z=1 to 3, is disclosed. The composition can be cured and used in a wide range of articles such as a photopolymer printing plate, sealant, caulk, encapsulent, road marking paint, photoresist, binder, impact modifier, polymer modifier, oxygen or water vapor barrier coating, conformal coating, solder mask, pigment dispersion, stereolithograph, laminating resin, grafted co-polymer, composite, optical fiber coating, paper coating, metal coating, glass coating, plastic coating, wood coating, waterproofing material, electrical insulating material, automotive belt or hose, tire, engine mount, gasket, golf ball core, and rubber roll.Type: GrantFiled: September 10, 2004Date of Patent: March 20, 2007Assignee: Sartomer Technology, Inc.Inventors: Jeffrey A. Klang, Yuhong He, Gary W. Ceska, James P. Horgan
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Patent number: 7192684Abstract: Polymerizable silicon-containing compounds of formula (1) wherein R1 is hydrogen, halogen or monovalent organic group are polymerized into polymers.Type: GrantFiled: September 29, 2003Date of Patent: March 20, 2007Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Takeshi Kinsho, Takeru Watanabe, Koji Hasegawa
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Patent number: 7192682Abstract: There is provided a chemically-amplified resist composition having high transparency to light having a wavelength of 220 nanometers or smaller, excellent resistance to etching, and excellent adhesion to a substrate. The chemically-amplified resist composition is prepared through the use of at least one of a repeated structural unit having a bridged alicyclic ?-lactone structure defined in the general formula (III), a repeated structural unit having a bridged alicyclic ?-lactone structure defined in the general formula (IV), and a repeated structural unit having a bridged alicyclic ?-lactone structure defined in the general formula (V).Type: GrantFiled: June 27, 2003Date of Patent: March 20, 2007Assignee: NEC CorporationInventors: Katsumi Maeda, Kaichiro Nakano
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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: 7189491Abstract: The present invention relates to a novel photoresist composition sensitive to radiation in the deep ultraviolet and a process for imaging the composition. The photoresist composition comprises a) a novel polymer that is insoluble in an aqueous alkaline solution and comprises at least one acid labile group, and b) a compound capable of producing an acid upon irradiation. The novel polymer of the present invention comprises at least one unit with a bisester group, (—C(O)OWC(O)O—), attached on one side to a polymer backbone unit (A) comprising an aliphatic group, and attached on the other side to an adamantyl group. The invention also relates to the novel polymer and a novel monomer for obtaining the novel polymer.Type: GrantFiled: December 11, 2003Date of Patent: March 13, 2007Assignee: AZ Electronic Materials USA Corp.Inventor: M. Dalil Rahman
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Patent number: 7189493Abstract: There is disclosed a polymer which at least has the repeating unit represented by the following general formula (1a), and the repeating unit represented by the following general formula (1b) and/or the repeating unit represented by the following general formula (1c), and a positive resist composition comprising the polymer as a base resin.Type: GrantFiled: September 21, 2004Date of Patent: March 13, 2007Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Jun Hatakeyama, Yuji Harada, Yoshio Kawai
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Patent number: 7189492Abstract: A photosensitive composition containing a compound capable of generating a specific acid having the plural number of sulfonic groups by irradiation with an actinic ray or a radiation and a pattern forming method using the same.Type: GrantFiled: September 10, 2004Date of Patent: March 13, 2007Assignee: Fuji Photo Film Co., Ltd.Inventors: Kunihiko Kodama, Kenji Wada, Kenichiro Satoh
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Patent number: 7186495Abstract: There are here disclosed a photoresist material for lithography using a light of 220 nm or less which comprises at least a polymer represented by the following formula (2) and a photo-acid generator for generating an acid by exposure: wherein R1, R2, R3 and R5 are each a hydrogen atom or a methyl group; R4 is an acid-labile group, an alicyclic hydrocarbon group having 7 to 13 carbon atoms, which has an acid labile group, an alicyclic hydrocarbon group having 7 to 13 carbon atoms, which has a carboxyl group, or a hydrocarbon group having 3 to 13 carbon atoms, which has an epoxy group; R6 is a hydrogen atom, a hydrocarbon group having 1 to 12 carbon atoms, or an alicyclic hydrocarbon group having 7 to 13 carbon atoms, which has a carboxyl group; x, y and z are optional values which meet x+y+z=1, 0<x?1, 0?y<1 and 0?z<1; and a weight-average molecular weight of the polymer is in the range of 2000 to 200000, and a resin having a (meth)acrylate unit of an alicyclic lactone structure represented by theType: GrantFiled: December 29, 2000Date of Patent: March 6, 2007Assignee: NEC CorporationInventors: Katsumi Maeda, Shigeyuki Iwasa, Kaichiro Nakano, Etsuo Hasegawa
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Patent number: 7179580Abstract: A copolymer expressed by the following structural formula was obtained by loading adamantyl methacrylate monomer and t-butyl acrylate monomer by 1:1, then conducting polymerization, adding AIBN as a polymerization initiator, and then conducting precipitation purification with methanol. Then to the copolymer, triphenylsulfonium hexafluoroantimonate was added to prepare a cyclohexanone solution. This solution was applied to a wafer, and exposed to a KrF excimer stepper and developed. The threshold energy Eth was 50 mJ/cm2. A 0.45 ?m-wide L & S was formed at 130 mJ/cm2. The radiation sensitive material has good transparency and etching resistance, high sensitivity, and little peeling.Type: GrantFiled: April 28, 2004Date of Patent: February 20, 2007Assignee: Fujitsu LimitedInventors: Satoshi Takechi, Makoto Takahashi, Yuko Kaimoto
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Patent number: 7179578Abstract: To provide a positive resist composition having high sensitivity, small defocus latitude depended on line pitch and less surface roughening at the etching, which can be suitably used for micro-photofabrication using far ultraviolet ray, particularly, ArF excimer laser ray. A positive resist composition comprising (A) a resin containing specific two kinds of repeating units, which has an aliphatic cyclic hydrocarbon group on the side chain and increases the dissolution rate in an alkali developer under the action of an acid, and (B) a specific compound capable of generating an acid upon irradiation with actinic rays or radiation, or a positive resist composition comprising (A) two kinds of resins as the resin having an aliphatic cyclic hydrocarbon group on the side chain and capable of increasing the dissolution rate in an alkali developer under the action of an acid, and (B) a compound capable of generating an acid upon irradiation with actinic rays or radiation.Type: GrantFiled: April 4, 2002Date of Patent: February 20, 2007Assignee: Fuji Photo Film Co., Ltd.Inventors: Kenichiro Sato, Kazuya Uenishi
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Patent number: 7179581Abstract: Resist compositions comprising nitrogen heterocyclic compounds having a pyrrole or nitrogen-bearing 5-membered ring structure and a polar functional group have an excellent resolution and an excellent focus margin and are useful in microfabrication using electron beams or deep-UV light.Type: GrantFiled: May 20, 2004Date of Patent: February 20, 2007Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Takeru Watanabe, Jun Hatakeyama
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Patent number: 7175963Abstract: A resin which comprises (1) at least one structural unit selected from the group consisting of a structural unit derived from 3-hydroxy-1-adamantyl (meth)acrylate, a structural unit derived from 3,5-dihydroxy-1-adamantyl (meth)acrylate, a structural unit derived from (meth)acryloyloxy-?-butyrolactone having a lactone ring optionally substituted by alkyl, a structural unit of the formula (Ia) and a structural unit of the formula and (2) a structural unit of the formula (II) and which itself is insoluble or poorly soluble in an alkali aqueous solution but becomes soluble in an alkali aqueous solution by the action of an acid; and also provides a chemical amplification type positive resist composition comprising a resin defined above and an acid generator.Type: GrantFiled: September 30, 2004Date of Patent: February 13, 2007Assignee: Sumitomo Chemical Company, LimitedInventors: Yusuke Fuji, Yoshiyuki Takata, Isao Yoshida
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Patent number: 7175949Abstract: A negative-working radiation-sensitive composition includes a polymeric binder comprising a polymer backbone and having attached thereto a carbazole derivative represented by the following Structure (I): wherein Y is a direct bond or a linking group, and R1 to R8 are independently hydrogen, or an alkyl, alkenyl, aryl, halo, cyano, alkoxy, acyl, acyloxy, or carboxylate groups, or any adjacent R1 through R8 groups can together form a carbocyclic or heterocyclic group or a fused aromatic ring. The composition can be sensitive to radiation having a maximum wavelength of from about 150 to about 1500 nm, and can be used to prepare negative-working imageable elements that be imaged and developed as lithographic printing plates.Type: GrantFiled: February 17, 2006Date of Patent: February 13, 2007Assignee: Eastman Kodak CompanyInventors: Ting Tao, Paul R. West, Scott A. Beckley, Nicki R. Miller
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Patent number: 7175967Abstract: Positive-working imageable elements are prepared by providing a first layer and second layers onto a substrate. Both layers include the same or different radiation absorbing compounds dispersed within different polymeric binders. After both layers are dried, they are heat treated at from about 40 to about 90° C. for at least 4 hours under conditions that inhibit the removal of moisture from the dried first and second layers. This method of preparation provides elements with improved imaging speed and good shelf life.Type: GrantFiled: March 2, 2006Date of Patent: February 13, 2007Assignee: Eastman Kodak CompanyInventors: James L. Mulligan, Eric Clark, Kevin B. Ray
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Patent number: 7172850Abstract: The present invention provides an imageable element including a lithographic substrate and an imageable layer disposed on the substrate. The imageable layer includes a radically polymerizable component, an initiator system capable of generating radicals sufficient to initiate a polymerization reaction upon exposure to imaging radiation, and a polymeric binder having a hydrophobic backbone and including both constitutional units having a pendant cyano group attached directly to the hydrophobic backbone, and constitutional units having a pendant group including a hydrophilic poly(alkylene oxide) segment. The invention also provides a method for preparing a suitable polymeric binder. The method comprises contacting a combination of co-monomers in a solvent mixture consisting essentially of a (C1–C6) alkanol and water.Type: GrantFiled: July 15, 2004Date of Patent: February 6, 2007Assignee: Eastman Kodak CompanyInventors: Heidi M. Munnelly, Kevin B. Ray, Ting Tao, Shashikant Saraiya, Kouji Hayashi, Jianbing Huang
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Patent number: 7169545Abstract: A resist exposure system and a method of forming a pattern on a resist are provided and include an exposure source, a photoresist composition, and a mask positioned therebetween. The resist composition comprises a first photoresist X and a second photoresist Y. The first photoresist X absorbs at a higher wavelength than the second photoresist Y. The second photoresist Y has a lower glass transitional temperature than the first photoresist X.Type: GrantFiled: August 19, 2004Date of Patent: January 30, 2007Assignee: Micron Technology, Inc.Inventor: Yoshiki Hishiro
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Patent number: 7169518Abstract: A positive-working imageable element comprises inner and outer layers and an infrared radiation absorbing compound such as an IR absorbing dye. The inner layer includes a first polymeric material. The ink receptive outer layer includes a second polymeric binder comprising pendant carboxy groups that provides improved chemical resistance to the imageable element and reduced residue from development.Type: GrantFiled: April 17, 2006Date of Patent: January 30, 2007Assignee: Eastman Kodak CompanyInventors: Celin Savariar-Hauck, Harald Baumann, Anthony P. Kitson
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Patent number: 7166413Abstract: By using a branched long chained chain scission polymer as a photoresist for EUV and 157 nanometer applications, a relatively higher molecular weight polymer with good mechanical properties may be achieved. In addition, by using chain scission technology, line edge roughness and resolution may be improved at the same time.Type: GrantFiled: October 12, 2004Date of Patent: January 23, 2007Assignee: Intel CorporationInventors: Heidi B. Cao, Robert P. Meagley
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Patent number: 7163770Abstract: A positive-working imageable element comprises inner and outer layers and a radiation absorbing compound such as an IR absorbing dye. The inner layer includes a first polymeric material. The ink receptive outer layer includes a second polymeric binder comprising a polymer backbone and an —X—C(?T)—NR—S(?O)2— moiety that is attached to the polymer backbone, wherein —X— is an oxy or —NR?— group, T is O or S, R and R? are independently hydrogen, halo, or an alkyl group having 1 to 6 carbon atoms. After thermal imaging, the element can be developed using an alkaline developer. Use of the particular second polymeric binder reduces sludging in the developer. Its dissolution rate in the developer is slow enough to resist developer attack in the non-imaged areas of the outer layer but rapid enough for the second polymeric binder to be quickly loosened from imaged areas and kept suspended or dissolved for a considerable time.Type: GrantFiled: January 23, 2006Date of Patent: January 16, 2007Assignee: Eastman Kodak CompanyInventors: Shashikant Saraiya, Anthony P. Kitson, Frederic E. Mikell, Larisa Novoselova
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Patent number: 7163781Abstract: According to the present invention, a resist resin having in its structure a specific bridged-bond-containing aliphatic ring, and a resist composition comprising the same are provided. By using this resist composition, a resist pattern excellent in both transparency against short-wavelength light and dry-etching resistance can be formed by alkali development with high resolution.Type: GrantFiled: September 10, 2004Date of Patent: January 16, 2007Assignee: Kabushiki Kaisha ToshibaInventors: Takeshi Okino, Koji Asakawa, Naomi Shida, Toru Ushirogouchi, Satoshi Saito
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Patent number: 7160666Abstract: A photosensitive resin composition of the present invention comprises (A) a resin having a repeating unit represented by formula (IA) and a repeating unit containing an acid decomposable group and copolymerizable with formula (IA), which is decomposed under the action of an acid to increase the solubility in an alkali developer, (B1) a compound capable of generating an aliphatic or aromatic sulfonic acid substituted by at least one fluorine atom upon irradiation with actinic rays or radiation, (B2) a compound capable of generating an aliphatic or aromatic sulfonic acid containing no fluorine atom, or an aliphatic or aromatic carboxylic acid upon irradiation with actinic rays or radiation, and (C) a solvent.Type: GrantFiled: March 5, 2003Date of Patent: January 9, 2007Assignee: Fuji Photo Film Co., Ltd.Inventors: Kazuyoshi Mizutani, Shinichi Kanna
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Patent number: 7160653Abstract: A positive-working imageable element comprises inner and outer layers and a radiation absorbing compound such as an IR absorbing dye. The inner layer includes a polymeric material that is removable using an alkaline developer. An ink receptive outer layer is not removable using an alkaline developer before its exposure to imaging radiation. The outer layer includes a polymer binder having pendant epoxy groups that are substantially unreacted during exposure.Type: GrantFiled: October 25, 2005Date of Patent: January 9, 2007Assignee: Eastman Kodak CompanyInventors: Jianbing Huang, Shashikant Saraiya, Kevin B. Ray, Anthony P. Kitson, Eugene L. Sheriff, Andrew Krebs
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Patent number: 7157208Abstract: A positive resist composition satisfying all of high sensitivity, high resolution, good pattern profile, good line edge roughness and good in-vacuum PED characteristics, is provided, the positive resist composition comprising: (A) a resin containing a repeating unit having a specific styrene skeleton, which is insoluble or hardly soluble in an alkali developer and becomes soluble in an alkali developer under the action of an acid; (B) a compound capable of generating an acid upon irradiation with actinic rays or radiation; and (C) an organic basic compound, and a pattern formation method using the positive resist composition.Type: GrantFiled: February 18, 2005Date of Patent: January 2, 2007Assignee: Fuji Photo Film Co., Ltd.Inventors: Tomoya Sasaki, Kazuyoshi Mizutani
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Patent number: 7157206Abstract: A positive resist composition comprising (A) a resin containing at least one group that is decomposed by the action of an acid to generate an alkali-soluble group and (B) at least two compounds selected from (B1) a compound that generates an aliphatic or aromatic sulfonic acid substituted with at least one fluorine atom, (B2) a compound that generates an aliphatic or aromatic sulfonic acid that does not contain a fluorine atom, (B3) a compound that generates an aliphatic or aromatic carboxylic acid substituted with at least one fluorine atom and (B4) a compound that generates an aliphatic or aromatic carboxylic acid that does not contain a fluorine atom, as (B) a compound that generates an acid upon irradiation of an actinic ray or radiation, wherein the group that is decomposed by the action of an acid contained in the resin (A) includes a group represented by formula (Y) defined in the specification.Type: GrantFiled: July 23, 2004Date of Patent: January 2, 2007Assignee: Fuji Photo Film Co., Ltd.Inventors: Haruki Inabe, Tomoya Sasaki
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Patent number: 7157207Abstract: Provided is a polymer useful as a base resin of a resist material featuring a high resolution, patterns with less sidewall roughness, practically acceptable etching resistance, and a substantial margin allowed for heat treatment temperature after exposure. The polymer has a weight-average molecular weight of from 1,000 to 50,000 and comprises at least one repeating unit of formula (1) below, at least one repeating unit of formula (2) below and at least one repeating unit of formula (3) below. A resist material comprising the polymer is also provided.Type: GrantFiled: September 1, 2004Date of Patent: January 2, 2007Assignee: Shin-etsu Chemical Co., Ltd.Inventors: Kenji Funatsu, Tsunehiro Nishi, Shigehiro Nagura
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Patent number: 7153632Abstract: A radiation-sensitive composition includes a radically polymerizable component that comprises carboxy groups, an initiator composition to generate radicals, and a polymeric binder comprising poly(alkylene oxide) segments and optionally pendant cyano groups. This composition can be used to prepare imageable elements such as negative-working, on-press developable printing plate precursors.Type: GrantFiled: August 3, 2005Date of Patent: December 26, 2006Assignee: Eastman Kodak CompanyInventors: Shashikant Saraiya, Heidi M. Munnelly, Frederic E. Mikell, Kevin D. Wieland
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Patent number: 7147985Abstract: A compound including a polymeric chain, an acid labile group attached to the polymeric chain, and at least one hydrophilic group attached to the acid labile group is disclosed. Compositions including the compound, and methods of using the compositions are also disclosed.Type: GrantFiled: March 31, 2004Date of Patent: December 12, 2006Assignee: Intel CorporationInventors: Wang Yueh, Ernisse S. Putna
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Patent number: 7147983Abstract: The present invention provides new photoresist compositions that comprise a resin binder, a photoactive component, particularly an acid generator, and a dye material that contains one or more chromophores that can reduce undesired reflections of exposure radiation. Preferred dye compounds are polymeric materials that include one or more chromophores such as anthracene and other polycyclic moieties that effectively absorb deep UV exposure radiation.Type: GrantFiled: October 7, 1996Date of Patent: December 12, 2006Assignee: Shipley Company, L.L.C.Inventors: James Michael Mori, James W. Thackeray, Roger F. Sinta, Rosemary Bell, Robin L. Miller-Fahey, Timothy G. Adams, Thomas M. Zydowsky, Edward K. Pavelchek, Manuel doCanto
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Patent number: 7147984Abstract: Disclosed is a positive-working chemical-amplification photoresist composition used in the patterning works in the manufacture of semiconductor devices, with which quite satisfactory patterning of a photoresist layer can be accomplished even on a substrate surface provided with an undercoating film of silicon nitride, phosphosilicate glass, borosilicate glass and the like in contrast to the prior art using a conventional photoresist composition with which satisfactory patterning can hardly be accomplished on such an undercoating film. The photoresist composition comprises, besides a film-forming resin capable of being imparted with increased solubility in an alkaline solution by interacting with an acid and a radiation-sensitive acid-generating compound, a phosphorus-containing oxo acid such as phosphoric acid and phosphonic acid or an ester thereof.Type: GrantFiled: March 29, 2004Date of Patent: December 12, 2006Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Hiroto Yukawa, Katsumi Oomori, Ryusuke Uchida, Yukihiro Sawayanagi
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Patent number: 7144678Abstract: A lithographic printing plate precursor comprises: a support; and an image-forming layer including a fluoroaliphatic group-containing copolymer, wherein the fluoroaliphatic group-containing copolymer contains a repeating unit corresponding to monomer (i) below and a repeating unit corresponding to monomer (ii) below: (i) a specified fluoroaliphatic group-containing monomer, and (ii) at least one of a poly(oxyalkylene) acrylate and a poly(oxyalkylene) methacrylate.Type: GrantFiled: April 1, 2002Date of Patent: December 5, 2006Assignee: Fuji Photo Film Co., Ltd.Inventors: Shiro Tan, Kazuo Fujita, Akira Nishioka
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Patent number: 7141352Abstract: Resist compositions comprising basic compounds having a benzimidazole skeleton and a polar functional group have an excellent resolution and an excellent focus margin and are useful in microfabrication using electron beams or deep-UV light.Type: GrantFiled: May 20, 2004Date of Patent: November 28, 2006Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Takeru Watanabe, Takeshi Kinsho, Koji Hasegawa
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Patent number: 7138217Abstract: A positive resist composition comprises: (A) a resin capable of decomposing by the action of an acid to increase the solubility in an alkali developer; and (B) a compound capable of generating an acid upon irradiation with one of an actinic ray and a radiation, wherein the resin (A) contains a specified repeating unit.Type: GrantFiled: March 19, 2002Date of Patent: November 21, 2006Assignee: Fuji Photo Film Co., Ltd.Inventors: Toshiaki Aoai, Kazuyoshi Mizutani, Shinichi Kanna
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Patent number: 7135268Abstract: The present invention provides a sulfonate of the formula (I?): wherein Q1, Q2, Q3, Q4 and Q5 each independently represent hydrogen, alkyl having 1 to 16 carbon atoms, alkoxy having 1 to 16 carbon atoms, or electron attractive group, with the proviso that at least one of Q1, Q2, Q3, Q4 and Q5 represents alkyl having 3 to 16 carbon atoms or alkoxy having 3 to 16 carbon atoms, and at least one of Q1, Q2, Q3, Q4 and Q5 is electron attractive group; and A?+ represents a counter ion of the formula (IIa), (IIb), (IIc) or (IId) which are identified in the specification.Type: GrantFiled: May 19, 2003Date of Patent: November 14, 2006Assignee: Sumitomo Chemical Company, LimitedInventors: Akira Kamabuchi, Yasunori Uetani, Hiroshi Moriuma
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Patent number: 7135267Abstract: The invention is directed to a photo-imageable composition precursor, the precursor composition comprising: (I) finely divided particles of inorganic material comprising: Functional phase particles selected from electrically conductive, resistive, and dielectric particles; inorganic binder having a glass transition temperature in the range of from 325 to 600° C.Type: GrantFiled: August 6, 2004Date of Patent: November 14, 2006Assignee: E. I. du Pont de Nemours and CompanyInventors: Haixin Yang, Mark Robert McKeever
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Patent number: 7135271Abstract: The positive type photosensitive composition of the present invention comprises a polymer compound (A) having, in a side chain thereof, a polymerizable group or a cross-linkable group, and an infrared absorbent (B). Preferably, the polymerizable group or cross-linkable group is incorporated into molecules of the polymer compound (A) through a structural unit having this group in a side chain thereof. Specifically, the structural unit is preferably a structural unit having any one of structures represented by the following general formulae (1) to (4): wherein A, B, X each independently represents a single bond, an oxygen atom, a sulfur atom or the like; L and M each independently represent a bivalent organic group; R1 to R12 represents a hydrogen atom or a monovalent organic group; R13 to R24 each independently represents a monovalent organic group; and Y represents an oxygen atom, a sulfur atom, or a phenylene group which may have a substituent.Type: GrantFiled: August 30, 2004Date of Patent: November 14, 2006Assignee: Fuji Photo Film Co., Ltd.Inventors: Ikuo Kawauchi, Ippei Nakamura
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Patent number: 7135270Abstract: A polymer comprising recurring units of formulae (1), (2), (3) and (4) increases a dissolution rate in an alkali developer under the action of an acid. R1, R2, R3 and R6 are H or CH3, R4 and R5 are H or OH, X is a tertiary exo-alkyl group having a bicyclo[2.2.1]heptane framework, represented by any of formulae (X-1) to (X-4): wherein R7 is C1–C10 alkyl, and Y is a tertiary alkyl group having an adamantane structure. A resist composition comprising the inventive polymer has a sensitivity to high-energy radiation, improved resolution and minimized proximity bias and lends itself to micropatterning with electron beams or deep UV for VLSI fabrication.Type: GrantFiled: August 5, 2004Date of Patent: November 14, 2006Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Takeru Watanabe, Tsunehiro Nishi, Junji Tsuchiya, Kenji Funatsu, Koji Hasegawa
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Patent number: 7132215Abstract: Novel ester compounds having formula (1) wherein A1 is a polymerizable functional group having a double bond, A2 is furandiyl, tetrahydrofurandiyl or oxanorbornanediyl, R1 and R2 each are a monovalent hydrocarbon group, or R1 and R2 may bond together to form an aliphatic hydrocarbon ring with the carbon atom, and R3 is hydrogen or a monovalent hydrocarbon group which may contain a hetero atom are polymerizable into polymers. Resist compositions comprising the polymers are sensitive to high-energy radiation, have an improved sensitivity, resolution, and etching resistance, and lend themselves to micropatterning with electron beams or deep-UV rays.Type: GrantFiled: September 29, 2003Date of Patent: November 7, 2006Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Koji Hasegawa, Takeshi Kinsho, Takeru Watanabe
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Patent number: 7132218Abstract: The present invention provide a chemically amplified positive resist composition comprising a resin which contains a structural unit having an acid labile group and which itself is insoluble or poorly soluble in an alkali aqueous solution and becomes soluble in an alkali aqueous solution by the action of an acid; an acid generator; and a compound of the formula (C-1) wherein R1 and R2 each independently represents a hydrogen or an alkyl having 1 to 4 carbon atoms, R3, R4 and R5 each independently represents a hydrogen or a hydroxyl.Type: GrantFiled: March 18, 2005Date of Patent: November 7, 2006Assignee: Sumitomo Chemical Company, LimitedInventors: Kouji Toishi, Yoshiyuki Takata, Satoshi Yamaguchi
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Patent number: 7129015Abstract: A polymer used for a negative type resist composition having a first repeating unit of a Si-containing monomer unit, a second repeating unit having a hydroxy group or an epoxy ring and copolymerized with the first repeating unit is provided. The first repeating unit is represented by the following formula: wherein R1 is a hydrogen atom or a methyl group, X is a C1–C4 alkyl or alkoxy group, and n is an integer from 2 to 4. Also, there is provided a negative type resist composition including the polymer which is an alkali soluble base polymer, a photoacid generator and a crosslinking agent cross linkable in the presence of an acid.Type: GrantFiled: November 6, 2003Date of Patent: October 31, 2006Assignee: Samsung Electronics Co., Ltd.Inventor: Sang-jun Choi
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Patent number: 7129022Abstract: This invention relates to a photo-polymerization type photosensitive electrode paste composition for a plasma display panel that is capable of preventing a bubble from occurring on an electrode surface during an electrode paste printing process and a damage of an electrode pattern caused by adhesive strength reduction, and a method of fabricating the electrode using the same. A photo-polymerization type photo-sensitive electrode paste composition for a PDP according to the present invention includes a binder polymer for increasing viscosity; at least one of a multi-functional monomer and a multi-functional oligomer that are combined in the shape of chain in reaction to a radical; metal powder; a frit glass for gluing the metal powder; and a photo-initiator and solvent for generating the radical in reaction to a light.Type: GrantFiled: November 27, 2002Date of Patent: October 31, 2006Assignee: LG Electronics Inc.Inventors: Sang Tae Kim, Seung Tae Park, Lee Soon Park, Jong Woo Park
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Patent number: 7129018Abstract: A negative photoresist composition is used for the formation of thick films and includes (A) a novolak resin, (B) a plasticizer, (C) a crosslinking agent and (D) an acid generator. The composition is applied onto a substrate and thereby yields a photoresist film 5 to 100 ?m thick. Likewise, the composition is applied onto a substrate of an electronic part, is patterned, is plated and thereby yields a bump.Type: GrantFiled: October 26, 2005Date of Patent: October 31, 2006Assignee: Toyko Ohka Kogyo Co., Ltd.Inventors: Koji Saito, Kouichi Misumi, Toshiki Okui, Hiroshi Komano
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Patent number: 7125643Abstract: A polymer comprising recurring units of formula (1) and recurring units of formulae (2a) to (2d) wherein R1 is F or fluoroalkyl, R2 is a single bond or an alkylene or fluoroalkylene, R3 and R4 are H, F, alkyl or fluoroalkyl, at least one of R3 and R4 contains F, R5 is H or an acid labile group, R6 is an acid labile group, adhesive group, alkyl or fluoroalkyl, and “a” is 1 or 2 is used as a base resin to formulate a resist composition which has advantages including high transparency to radiation having a wavelength of up to 200 nm, substrate adhesion, developer affinity and dry etching resistance.Type: GrantFiled: October 21, 2004Date of Patent: October 24, 2006Assignees: Shin-Etsu Chemical Co., Ltd., Matsushita Electric Industrial Co., Ltd., Central Glass Co., Ltd.Inventors: Yuji Harada, Jun Hatakeyama, Yoshio Kawai, Masaru Sasago, Masayuki Endo, Shinji Kishimura, Kazuhiko Maeda, Haruhiko Komoriya, Kazuhiro Yamanaka
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Patent number: 7125640Abstract: A photoresist contains a polymer that has no silicon-containing groups. Consequently, no expulsion of silicon-containing compounds in gaseous form occurs on exposure to short-wave radiation. The polymer is obtained by terpolymerization of a first comonomer having a group cleavable under acid catalysis, a second comonomer having an anchor group, and a monounsaturated hydrocarbon, in which individual carbon atoms of the carbon skeleton may also be replaced by oxygen, as a third comonomer. The polymer has a low glass transition temperature, and the photoresist therefore has a good layer quality on film formation and good structurability.Type: GrantFiled: January 31, 2003Date of Patent: October 24, 2006Assignee: Infineon Technologies AGInventors: Jörg Rottstegge, Michael Sebald
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Patent number: 7125642Abstract: A sulfonate compound having formula (1) is novel wherein R1 to R3 are H, F or C1-20 alkyl or fluoroalkyl, at least one of R1 to R3 contains F.Type: GrantFiled: February 9, 2004Date of Patent: October 24, 2006Assignees: Shin-Etsu Chemical Co., Ltd., Matsushita Electric Industrial Co., Ltd., Central Glass Co., Ltd.Inventors: Yuji Harada, Jun Hatakeyama, Yoshio Kawai, Masaru Sasago, Masayuki Endo, Shinji Kishimura, Kazuhiko Maeda, Haruhiko Komoriya, Satoru Miyazawa
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Patent number: 7125943Abstract: A fluorine-containing compound represented by the formula 1, where R1 is a methyl group or trifluoromethyl group, each of R2 and R3 is independently a hydrogen atom or a group containing (a) a hydrocarbon group having a straight-chain, branched or ring form and having a carbon atom number of 1–25 or (b) an aromatic hydrocarbon group, each of the hydrogen group and the aromatic hydrocarbon group independently optionally containing at least one of a fluorine atom, an oxygen atom and a carbonyl bond, l is an integer of from 0 to 2, each of m and n is independently an integer of 1–5 to satisfy an expression of m+n?6, and when at least one of R1, R2 and R3 is present in a plural number, the at least one of R1, R2 and R3 may be identical with or different from each other.Type: GrantFiled: August 6, 2003Date of Patent: October 24, 2006Assignee: Central Glass Company, LimitedInventors: Shinichi Sumida, Haruhiko Komoriya, Kazuhiko Maeda
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Patent number: 7122292Abstract: The present invention relates to novel first to fourth lactone compounds. The first lactone compound is represented by the formula (1), in the formula, X represents CH2, CH2CH2, O, S or NR1, and R1 represents hydrogen atom, a straight-chain, branched or cyclic alkyl group of a carbon number of 1–10. Hydrogen(s) of the alkyl group may partially or entirely be replaced with fluorine atom(s). Furthermore, a part of the alkyl group may contain an atomic group containing oxygen atom, sulfur atom, nitrogen atom, carbon-carbon double bond, carbonyl group, hydroxy group or carboxyl group.Type: GrantFiled: December 30, 2004Date of Patent: October 17, 2006Assignee: Central Glass Company, LimitedInventors: Shinichi Sumida, Haruhiko Komoriya, Katsutoshi Suzuki, Kazuhiko Maeda
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Patent number: 7122293Abstract: A polymer, which contains a structural unit having a carboxyl group represented by the following formula (1) at a side chain of the structural unit, wherein no deposition is formed, when the polymer is dissolved in an alkali aqueous solution having a pH of 10 or more and kept at 25° C. for 60 days: wherein R1 represents a hydrogen atom or a methyl group; R2 represents an (n+1)-valent organic linking group containing an ester group represented by —O(C?O)—; A represents an oxygen atom or NR3—; R3 represents a hydrogen atom, or an monovalent hydrocarbon group having from 1 to 10 carbon atoms; and n indicates an integer of from 1 to 5.Type: GrantFiled: July 28, 2004Date of Patent: October 17, 2006Assignee: Fuji Photo Film Co., Ltd.Inventors: Atsushi Sugasaki, Kazuto Kunita