Patents by Inventor Toshinobu Ishihara
Toshinobu Ishihara has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 5814694Abstract: A water-soluble coating composition for forming a layer to be placed on the upper surface of a resist is provided without use of Freons. The material includes an aqueous solution containing a) at least one water-soluble polymer selected from the group consisting of poly(N-vinylpyrrolidone) homopolymers and water-soluble copolymers of N-vinylpyrrolidone and other vinyl monomers, b) at least one fluorine-containing organic acid, and c) at least one amino acid derivative. The film formed through use of the material of the invention serves as both an anti-reflective film and a protective film. The material of the present invention provides a number of advantages in the formation of resist patterns, including excellent film-forming properties, excellent dimensional accuracy and aligning accuracy, simple and easy handling, high productivity, and good reproducibility.Type: GrantFiled: April 3, 1997Date of Patent: September 29, 1998Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Satoshi Watanabe, Shigehiro Nagura, Toshinobu Ishihara
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Patent number: 5795700Abstract: A resist pattern is formed on a substrate by forming a water-soluble resist film on the substrate, forming a contrast enhancing film on the resist film from a contrast enhancing composition comprising a specific arylnitrone compound of formula (1), pre-baking the resist film before or after formation of the contrast enhancing film, exposing the resist film to light through the contrast enhancing film, baking the films after exposure, removing the contrast enhancing film after the baking step, and developing the resist film. The process forms a resist pattern having a fully rectangular profile and an improved focus margin. The conventional apparatus can be utilized without substantial modification, achieving a cost reduction. ##STR1## wherein R.sup.1, R.sup.2, and R.sup.3 are independently an alkyl radical, an aryl radical or a hydrogen atom,R.sup.4 to R.sup.8 are independently an alkyl radical, a hydrogen atom or a carboxyl radical, at least one of R.sup.4 to R.sup.Type: GrantFiled: February 21, 1996Date of Patent: August 18, 1998Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Jun Hatakeyama, Mitsuo Umemura, Toshinobu Ishihara, Satoshi Watanabe
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Patent number: 5783717Abstract: A method for purifying an organometal compound by removing oxygen atom-containing compounds included in the organometal compound as impurities is herein disclosed. The method comprises the steps of mixing an organometal compound represented by the following formula: ##STR1## with a crude product including an oxygen atom-containing compound represented by the following formula: R.sub.3-n M.sup.1 (OR).sub.n or R.sub.2-m M.sup.2 (OR).sub.m and an alkylaluminum chloride represented by the formula: X.sub.6-q Al.sub.2 R and then distilling the resulting mixture. In the foregoing formulas, R's may be the same or different and each represents an alkyl group having 1 to 3 carbon atoms; M.sup.1 represents a trivalent metal element; M.sup.2 represents a divalent metal element; n is an integer of 1, 2 or 3; m is an integer of 1 or 2; q is an integer ranging from 1 to 5; and X represents a chlorine atom.Type: GrantFiled: August 21, 1995Date of Patent: July 21, 1998Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Hiromi Ohsaki, Toshinobu Ishihara, Kazuyuki Asakura, Isao Kaneko, Kouhei Satou
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Patent number: 5772925Abstract: An anti-reflective coating composition comprising a polyimide dissolved in an organic solvent is used to form an anti-reflective coating beneath a chemical amplification type resist layer. The composition allows a fine resist pattern to be formed with high accuracy in a convenient, efficient, reproducible manner.Type: GrantFiled: July 10, 1997Date of Patent: June 30, 1998Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Satoshi Watanabe, Toshinobu Ishihara, Ichiro Kaneko, Katsuyuki Oikawa, Yoshihumi Takeda
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Patent number: 5773200Abstract: A positive resist composition contains (1) a novolak resin having a weight average molecular weight calculated as polystyrene of 2,000-10,000 as an alkali-soluble resin, (2) a low nucleus compound having a phenolic hydroxyl group and 2-5 benzene rings as a dissolution promoter, and (3) a compound having a 1,2-naphthoquinonediazidosulfonyl group in a molecule and a degree of esterification of at least 65% as a photosensitive agent. By forming a resist layer on a substrate from the positive resist composition, and baking the resist layer at 100.degree.-130.degree. C. before exposure or before development, followed by exposure and development, there is formed a resist pattern having a micro-groove of desired configuration. This resist pattern lends itself to a lift-off technique.Type: GrantFiled: December 15, 1995Date of Patent: June 30, 1998Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Satoshi Okazaki, Kazuhiro Nishikawa, Masaru Kobayashi, Miki Kobayashi, Mitsuo Umemura, Toshinobu Ishihara
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Patent number: 5759739Abstract: A resist composition comprising an alkali-soluble resin, typically a partially t-butoxycarbonylated polyhydroxystyrene, a p-butoxystyrene/t-butylacrylate copolymer or p-butoxystyrene/maleic anhydride copolymer as a dissolution inhibitor, and a iodonium or sulfonium salt as a photoacid generator is effective for forming a resist film which can be precisely and finely patterned using high energy radiation such as a KrF excimer laser.Type: GrantFiled: April 22, 1996Date of Patent: June 2, 1998Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Katsuya Takemura, Toshinobu Ishihara, Kazumasa Maruyama, Yoshihumi Takeda, Minoru Shigemitsu, Ken'ichi Itoh
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Patent number: 5750309Abstract: In a chemical amplification positive resist composition comprising an organic solvent, a resin and a photoacid generator, at least two polymers having different molecular weights selected from polyhydroxystyrenes having some hydroxyl groups protected with acid labile groups are used. Among the polymers, a high molecular weight polymer has a molecular weight dispersity (Mw1/Mn1) of up to 1.5, and a low molecular weight polymer has a dispersity (Mw2/Mn2) of up to 5.0. The weight average molecular weight ratio Mw1/Mw2 is between 1.5/1 and 10.0/1. The resist composition is highly sensitive to actinic radiation, has improved sensitivity and resolution, and is suitable for use in a fine patterning technique and commercially acceptable.Type: GrantFiled: July 19, 1996Date of Patent: May 12, 1998Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Jun Hatakeyama, Shigehiro Nagura, Kiyoshi Motomi, Takeshi Nagata, Toshinobu Ishihara
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Patent number: 5731126Abstract: A chemically amplified positive resist composition comprising a specific polysiloxane having a terminal silanol group protected with a trimethylsilyl group, a photoacid generator and optionally a dissolution inhibitor is provided.Type: GrantFiled: April 3, 1996Date of Patent: March 24, 1998Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Katsuya Takemura, Junji Tsuchiya, Toshinobu Ishihara
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Patent number: 5728508Abstract: A method of forming a resist pattern comprising forming a photoresist layer on a substrate, forming a transparent anti-reflective film on said photoresist layer by applying an anti-reflective material onto said photoresist layer, said anti-reflective material comprising a fluorinated resin which is soluble in an organic hydrocarbon solvent, exposing a light to said resist layer through said transparent anti-reflective film, removing said anti-reflective film using an organic hydrocarbon solvent, and developing said photoresist layer.Type: GrantFiled: July 1, 1996Date of Patent: March 17, 1998Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Katsuya Takemura, Toshinobu Ishihara, Satoshi Watanabe, Kazumasa Maruyama, Hirofumi Kishita, Kouichi Yamaguchi
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Patent number: 5705702Abstract: By reacting an aryl Grignard reagent of the following general formula (1) with thionyl chloride and then reacting the reaction product with a triorganosilyl sulfonate or triorganohalide of the general formula (2): (R.sup.6).sub.3 SiY wherein R.sup.6, which may be the same or different, is a monovalent hydrocarbon group and Y is a substituted or unsubstituted alkylsulfonate or arylsulfonate or halogen atom, there is prepared a triarylsulfonium salt of the following general formula (3). ##STR1## In the formulae, each of R.sup.1 to R.sup.5, which may be the same or different, is a hydrogen atom or a monovalent organic group, especially alkyl, aryl, alkoxy, aryloxy, dialkylamino, dialkylaminoalkyl, alkylthio or arylthio group and X is a bromine or chlorine atom.Type: GrantFiled: September 12, 1996Date of Patent: January 6, 1998Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Yoichi Osawa, Satoshi Watanabe, Junji Shimada, Toshinobu Ishihara
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Patent number: 5691396Abstract: The invention provides a novel polysiloxane compound, typically polyhydroxybenzylsilsesquioxane, having some hydroxyl groups replaced by acetal groups and optionally acid labile groups. The polysiloxane compound is useful as an alkali soluble polymer for positive resist material.Type: GrantFiled: September 24, 1996Date of Patent: November 25, 1997Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Katsuya Takemura, Junji Tsuchiya, Osamu Watanabe, Toshinobu Ishihara
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Patent number: 5691112Abstract: Trifluoromethanesulfonic and p-toluenesulfonic acid bis- or tris(p-tert-butoxyphenyl)sulfonium salts are novel. They are prepared from bis(p-tert-butoxyphenyl)sulfoxide which is also novel. A chemically amplified positive resist composition which contains the sulfonium salt as a photo-acid generator is highly sensitive to deep-UV rays, electron beams and X-rays, can be developed with alkaline aqueous solution to form a pattern, and is thus suitable for use in a fine patterning technique.Type: GrantFiled: December 10, 1996Date of Patent: November 25, 1997Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Satoshi Watanabe, Youichi Ohsawa, Toshinobu Ishihara, Kazumasa Maruyama, Yoshihumi Takeda, Junji Shimada, Fujio Yagihashi, Katsuya Takemura
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Patent number: 5633409Abstract: Trifluoromethanesulfonic and p-toluenesulfonic acid bis- or tris(p-tert-butoxyphenyl)sulfonium salts are novel. They are prepared from bis(p-tert-butoxyphenyl)sulfoxide which is also novel. A chemically amplified positive resist composition which contains the sulfonium salt as a photo-acid generator is highly sensitive to deep-UV rays, electron beams and X-rays, can be developed with alkaline aqueous solution to form a pattern, and is thus suitable for use in a fine patterning technique.Type: GrantFiled: January 27, 1995Date of Patent: May 27, 1997Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Satoshi Watanabe, Youichi Ohsawa, Toshinobu Ishihara, Kazumasa Maruyama, Yoshihumi Takeda, Junji Shimada, Fujio Yagihashi, Katsuya Takemura
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Patent number: 5629134Abstract: In a chemically amplified positive resist composition comprising an organic solvent, an alkali soluble resin, an acid generator, and an optional dissolution inhibitor, a salt of a pyridine which may have an alkyl, alkoxy, amino or dialkylamino group with an alkylsulfonic acid, arylsulfonic acid or halogen atom is blended. Because of high sensitivity to deep UV and resolution and elimination of the PED problem causing T-top pattern configuration and the skirting phenomenon, the resist composition is improved in dimensional precision and lends itself to fine patterning.Type: GrantFiled: October 6, 1995Date of Patent: May 13, 1997Assignees: Shin-Etsu Chemical Co., Ltd., Nippon Telegraph and Telephone Corp.Inventors: Katsuyuki Oikawa, Toshinobu Ishihara, Fujio Yagihashi, Akinobu Tanaka, Yoshio Kawai, Jiro Nakamura
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Patent number: 5624787Abstract: A chemically amplified, positive resist composition contains a trifluoromethanesulfonic or p-toluenesulfonic acid bis- or tris(p-tert-butoxyphenyl)sulfonium salt and a nitrogenous compound. The composition is highly sensitive to high energy radiation, especially KrF excimer laser and has high sensitivity, resolution and plasma etching resistance while the resulting resist pattern is heat resistant.Type: GrantFiled: June 6, 1995Date of Patent: April 29, 1997Assignees: Shin-Etsu Chemical Co., Ltd., Nippon Telegraph and Telephone Corp.Inventors: Satoshi Watanabe, Katsuyuki Oikawa, Toshinobu Ishihara, Akinobu Tanaka, Tadahito Matsuda, Yoshio Kawai
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Patent number: 5612170Abstract: A positive resist composition based on a silicone polymer contains a photo acid generator which will decompose to generate an acid upon exposure to radiation. The silicone polymer includes hydroxybenzyl units wherein some OH groups are replaced by t-butoxycarbonyl, t-butoxycarbonylmethyl, trimethylsilyl or tetrahydropyranyl groups. In a first form, the photo acid generator is a specific onium salt having at least one phenyl group with a t-alkoxy, t-butoxycarbonyloxy or t-butoxycarbonylmethoxy substituent. In a second form, the composition further contains a nitrogenous compound. In a third form, the composition further contains a dissolution inhibitor in the form of a specific silicone compound. The composition is sensitive to high energy radiation and has high sensitivity and resolution.Type: GrantFiled: December 8, 1995Date of Patent: March 18, 1997Assignees: Shin-Etsu Chemical Co., Ltd., Nippon Telegraph and Telephone CompanyInventors: Katsuya Takemura, Junji Tsuchiya, Toshinobu Ishihara, Akinobu Tanaka, Yoshio Kawai, Jiro Nakamura
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Patent number: 5580936Abstract: A partially tert-butoxylated poly(p-hydroxystyrene) is prepared by subjecting poly(p-tert-butoxystyrene) to reaction of eliminating some of the tert-butoxy groups in an organic solvent at a temperature of 30.degree.-100.degree. C. in the presence of an acid catalyst at a molar ratio of acid catalyst/t-BuO group of from 0.050 to 2.0. During the elimination reaction, a change of solubility of the resulting partially tert-butoxylated poly(p-hydroxystyrene) is determined to calculate a degree of elimination of tert-butoxy groups. The reaction is terminated when a desired degree of elimination is reached. Through a simple process, partially tert-butoxylated poly(p-hydroxystyrene) having a well controlled t-BuO content is produced in high yields.Type: GrantFiled: September 29, 1995Date of Patent: December 3, 1996Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Junji Tsuchiya, Katsuya Takemura, Osamu Watanabe, Yoshihumi Takeda, Toshinobu Ishihara
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Patent number: 5569784Abstract: A novel sulfonium salt having at least one substituted aromatic group having acid labile groups and at least one nitrogenous aromatic group is provided. A chemically amplified, positive resist composition comprising the sulfonium salt as well as an alkali soluble resin and a dissolution inhibitor in an organic solvent has solved the PED problem.Type: GrantFiled: January 27, 1995Date of Patent: October 29, 1996Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Satoshi Watanabe, Junji Shimada, Youichi Ohsawa, Katsuya Takemura, Toshinobu Ishihara, Kazumasa Maruyama
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Patent number: 5529888Abstract: A water-soluble composition comprising a water-soluble N-vinylpyrrolidone copolymer and a fluorinated organic acid in a weight ratio of from 20:80 to 70:30 is useful in forming a water-soluble overlying film on a chemically amplified resist layer. The overlying film functions as both an anti-reflective film and a protective film during resist pattern formation by photolithography.Type: GrantFiled: September 20, 1995Date of Patent: June 25, 1996Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Satoshi Watanabe, Toshinobu Ishihara, Yoshihumi Takeda, Katsuyuki Oikawa
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Patent number: 5461166Abstract: Disclosed are a conductive thienyl derivative monomolecular film covalently bonded to a substrate surface and method of manufacturing the same, and a silicon compound comprising 3-thienyl groups (thiophene derivative) used for forming the conductive monomolecular film and a method of manufacturing the same. A monomolecular ultrathin film comprising 3-thienyl groups and silicon groups is formed in the invention. The silicon compound used for forming the film is provided by reacting .omega.-(3-thienyl)-1-alkene compound to a monosilane derivative compound, in which three out of four hydrogen atoms of monosilane are replaced with halogen or alkoxy groups, in the presence of a transition metal catalyst. A substrate is dipped and held in a nonaqueous solution of the above-noted compound, thus chemically bonding the monomolecular film to the substrate surface. Furthermore, a thienyl derivative ultrathin film is formed by the electrolytic or catalytic polymerization of the monomolecular film.Type: GrantFiled: February 3, 1995Date of Patent: October 24, 1995Assignee: Matsushita Electric Industrial Co., Ltd.Inventors: Norihisa Mino, Kazufumi Ogawa, Toshinobu Ishihara, Mikio Endo, Tohru Kubota, Kazuyuki Asakura