Patents by Inventor Takehisa Ishimaru
Takehisa Ishimaru 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: 9983475Abstract: Non-ionic photo-acid generating (PAG) compounds were prepared that contain an aryl ketone group having a perfluorinated substituent alpha to the ketone carbonyl. The non-polymeric PAGs release a sulfonic acid when exposed to high energy radiation such as deep UV or extreme UV light. The photo-generated sulfonic acid has a low diffusion rate in an exposed resist layer subjected to a post-exposure bake (PEB) at 100° C. to 150° C., resulting in formation of good line patterns after development. At higher temperatures, the PAGs can also undergo a thermal reaction to form a sulfonic acid. The perfluorinated substituent provides improved thermal stability and hydrolytic/nucleophilic stability.Type: GrantFiled: August 12, 2016Date of Patent: May 29, 2018Assignees: International Business Machines Corporation, Central Glass Co., Ltd.Inventors: Takehisa Ishimaru, Satoru Narizuka, Daniel P. Sanders, Ratnam Sooriyakumaran, Hoa D. Truong, Rudy J. Wojtecki
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Patent number: 9950999Abstract: Non-ionic photo-acid generating (PAG) compounds were prepared that contain an aryl ketone group. The disclosed non-polymeric PAGs release a strong sulfonic acid when exposed to high energy radiation such as deep UV or extreme UV light. The photo-generated sulfonic acid has a low diffusion rate in an exposed resist layer subjected to a post-exposure bake (PEB) at 100° C. to 150° C., resulting in formation of good line patterns after development. At higher temperatures, the PAGs undergo a thermal reaction to form a sulfonic acid.Type: GrantFiled: August 12, 2016Date of Patent: April 24, 2018Assignees: International Business Machines Corporation, Central Glass Co., Ltd.Inventors: Takehisa Ishimaru, Satoru Narizuka, Daniel P. Sanders, Ratnam Sooriyakumaran, Hoa D. Truong, Rudy J. Wojtecki
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Patent number: 9951164Abstract: Non-ionic photo-acid generating (PAG) polymerizable monomers were prepared that contain a side chain sulfonate ester of an alpha-hydroxy aryl ketone. The aryl ketone group has a perfluorinated substituent alpha to the ketone carbonyl. The sulfur of the sulfonate ester is also directly linked to a fluorinated group. PAG polymers prepared from the PAG monomers release a strong sulfonic acid when exposed to high energy radiation such as deep UV or extreme UV light. The photo-generated sulfonic acid has a low diffusion rate in an exposed resist layer subjected to a post-exposure bake (PEB) at 100° C. to 150° C., resulting in formation of good line patterns after development.Type: GrantFiled: August 12, 2016Date of Patent: April 24, 2018Assignees: International Business Machines Corporation, Central Glass Co., Ltd.Inventors: Takehisa Ishimaru, Satoru Narizuka, Daniel P. Sanders, Ratnam Sooriyakumaran, Hoa D. Truong, Rudy J. Wojtecki
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Publication number: 20180044459Abstract: Non-ionic photo-acid generating (PAG) polymerizable monomers were prepared that contain a side chain sulfonate ester of an alpha-hydroxy aryl ketone. The aryl ketone group has a perfluorinated substituent alpha to the ketone carbonyl. The sulfur of the sulfonate ester is also directly linked to a fluorinated group. PAG polymers prepared from the PAG monomers release a strong sulfonic acid when exposed to high energy radiation such as deep UV or extreme UV light. The photo-generated sulfonic acid has a low diffusion rate in an exposed resist layer subjected to a post-exposure bake (PEB) at 100° C. to 150° C., resulting in formation of good line patterns after development.Type: ApplicationFiled: August 12, 2016Publication date: February 15, 2018Inventors: Takehisa Ishimaru, Satoru Narizuka, Daniel P. Sanders, Ratnam Sooriyakumaran, Hoa D. Truong, Rudy J. Wojtecki
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Publication number: 20180044284Abstract: Non-ionic photo-acid generating (PAG) compounds were prepared that contain an aryl ketone group. The disclosed non-polymeric PAGs release a strong sulfonic acid when exposed to high energy radiation such as deep UV or extreme UV light. The photo-generated sulfonic acid has a low diffusion rate in an exposed resist layer subjected to a post-exposure bake (PEB) at 100° C. to 150° C., resulting in formation of good line patterns after development. At higher temperatures, the PAGs undergo a thermal reaction to form a sulfonic acid.Type: ApplicationFiled: August 12, 2016Publication date: February 15, 2018Inventors: Takehisa Ishimaru, Satoru Narizuka, Daniel P. Sanders, Ratnam Sooriyakumaran, Hoa D. Truong, Rudy J. Wojtecki
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Publication number: 20180046077Abstract: Non-ionic photo-acid generating (PAG) compounds were prepared that contain an aryl ketone group having a perfluorinated substituent alpha to the ketone carbonyl. The non-polymeric PAGs release a sulfonic acid when exposed to high energy radiation such as deep UV or extreme UV light. The photo-generated sulfonic acid has a low diffusion rate in an exposed resist layer subjected to a post-exposure bake (PEB) at 100° C. to 150° C., resulting in formation of good line patterns after development. At higher temperatures, the PAGs can also undergo a thermal reaction to form a sulfonic acid. The perfluorinated substituent provides improved thermal stability and hydrolytic/nucleophilic stability.Type: ApplicationFiled: August 12, 2016Publication date: February 15, 2018Inventors: Takehisa Ishimaru, Satoru Narizuka, Daniel P. Sanders, Ratnam Sooriyakumaran, Hoa D. Truong, Rudy J. Wojtecki
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Patent number: 9244345Abstract: Photo-acid generating vinyl polymerizable monomers (PAG monomers) were prepared comprising sulfonate ester groups of N-hydroxide imides. The photo-acid generating portion of the PAG monomer is linked to a polymerizable portion of the monomer by an amide linking group. Photo-acid generating polymers (PAG polymers) of the PAG monomers show high sensitivity to extreme ultraviolet radiation (13.5 nm) and much less sensitivity to far ultraviolet wavelengths (193 nm, 248 nm). The PAG polymers also exhibit thermal and chemical amplification properties useful for forming high resolution positive tone or negative tone lithographic resist patterns.Type: GrantFiled: November 6, 2014Date of Patent: January 26, 2016Assignees: International Business Machines Corporation, Central Glass Co., LTD.Inventors: Takehisa Ishimaru, Satoru Narizuka, Daniel P. Sanders, Ratnam Sooriyakumaran, Hoa D. Truong, Rudy J. Wojtecki, Manabu Yasumoto
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Patent number: 9040745Abstract: A production process of a fluorosulfuric acid aromatic-ring ester according to the present invention includes reaction of an aromatic-ring hydroxyl compound with sulfuryl fluoride (SO2F2) in the presence of a tertiary amine except pyridine and methylpyridine. The sulfuryl fluoride, used as the reactant in the production process according to the present invention, is widely adapted as a fumigant and is easily available on a large scale. Further, the target compound can be obtained rapidly with a high yield under moderate reaction conditions in the production process according to the present invention. In this way, all of the prior art problems can be solved in the production process according to the present invention. The production process according to the present invention is thus particularly useful for industrial production of the fluorosulfuric acid aromatic-ring ester.Type: GrantFiled: June 15, 2012Date of Patent: May 26, 2015Assignee: Central Glass Company, LimitedInventors: Akihiro Ishii, Takehisa Ishimaru, Takako Yamazaki, Manabu Yasumoto
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Publication number: 20140114088Abstract: A production process of a fluorosulfuric acid aromatic-ring ester according to the present invention includes reaction of an aromatic-ring hydroxyl compound with sulfuryl fluoride (SO2F2) in the presence of a tertiary amine except pyridine and methylpyridine. The sulfuryl fluoride, used as the reactant in the production process according to the present invention, is widely adapted as a fumigant and is easily available on a large scale. Further, the target compound can be obtained rapidly with a high yield under moderate reaction conditions in the production process according to the present invention. In this way, all of the prior art problems can be solved in the production process according to the present invention. The production process according to the present invention is thus particularly useful for industrial production of the fluorosulfuric acid aromatic-ring ester.Type: ApplicationFiled: June 15, 2012Publication date: April 24, 2014Applicant: Central Glass Company, LimitedInventors: Akihiro Ishii, Takehisa Ishimaru, Takako Yamazaki, Manabu Yasumoto
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Patent number: 8658840Abstract: A production method of a ?-fluoroalcohol includes performing a reaction of an ?-fluoroester with hydrogen gas (H2) in the presence of a specific ruthenium complex (i.e. a ruthenium complex of the general formula [2], preferably a ruthenium complex of the general formula [4]). This production method can employ a suitable hydrogen pressure of 1 MPa or less by the use of such a specific ruthenium complex and does not require a high-pressure gas production facility when put in industrial practice. In addition, this production method can remarkably reduce the amount of catalyst used therein (to e.g. a substrate/catalyst ratio of 20,000) in comparison to the substrate/catalyst ratio conventional reduction of ?-fluoroalcohol. It is possible by these reduction in hydrogen pressure and catalyst amount to largely reduce the production cost of the ?-fluoroalcohol.Type: GrantFiled: January 27, 2012Date of Patent: February 25, 2014Assignee: Central Glass Company, LimitedInventors: Akihiro Ishii, Takashi Ootsuka, Takehisa Ishimaru, Mari Imamura
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Publication number: 20130303774Abstract: A production method of a ?-fluoroalcohol includes performing a reaction of an ?-fluoroester with hydrogen gas (H2) in the presence of a specific ruthenium complex (i.e. a ruthenium complex of the general formula [2], preferably a ruthenium complex of the general formula [4]). This production method can employ a suitable hydrogen pressure of 1 MPa or less by the use of such a specific ruthenium complex and does not require a high-pressure gas production facility when put in industrial practice. In addition, this production method can remarkably reduce the amount of catalyst used therein (to e.g. a substrate/catalyst ratio of 20,000) in comparison to the substrate/catalyst ratio conventional reduction of ?-fluoroalcohol. It is possible by these reduction in hydrogen pressure and catalyst amount to largely reduce the production cost of the ?-fluoroalcohol.Type: ApplicationFiled: January 27, 2012Publication date: November 14, 2013Applicant: Central Glass Company, LimitedInventors: Akihiro Ishii, Takashi Ootsuka, Takehisa Ishimaru, Mari Imamura
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Publication number: 20110237824Abstract: Aminoethanol is reacted with a fluoroalkylsulfonic anhydride to obtain a fluoroalkylsulfonylaminoethanol (first step: sulfonylamidation step). The fluoroalkylsulfonylaminoethanol is esterified with an ?-substituted acrylate derivative to obtain a desired fluoroalkylsulfonylaminoethyl ?-substituted-acrylate (second step: esterification step). Thus, the desired fluoroalkylsulfonylaminoethyl ?-substituted-acrylate having a higher purity can be produced in higher yield with higher operating efficiency than in conventional techniques.Type: ApplicationFiled: December 22, 2009Publication date: September 29, 2011Applicant: Central Glass Company, LimitedInventors: Takehisa Ishimaru, Ryo Nadano, Makoto Matsuura