And Monomeric Processing Ingredient Patents (Class 430/191)
  • Patent number: 6406827
    Abstract: A positive photoresist composition includes (A) an alkali-soluble resin, (B) a quinonediazide ester of, e.g., bis[2,5-dimethyl-3-(2-hydroxy-5-methylbenzyl)-4-hydroxyphenyl]methane and/or 2,4-bis[4-hydroxy-3-(4-hydroxybenzyl)-5-methylbenzyl]-6-cyclohexylphenol, and (C) 4,4′-bis(diethylamino)benzophenone. The composition exhibits high sensitivity and definition and improved focal depth range properties and underexposure margin.
    Type: Grant
    Filed: May 28, 1999
    Date of Patent: June 18, 2002
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Takako Suzuki, Kousuke Doi, Hidekatsu Kohara, Toshimasa Nakayama
  • Publication number: 20020068235
    Abstract: The present invention relates to a photosensitive compound comprising a vinyl polymer compound which is insoluble in water and soluble in an aqueous alkaline solution and o-naphthoquinonediazide compound, wherein said vinyl polymer compound is a copolymer comprising at least one monomer unit derived from monomer compound (A): a compound having an alkaline-soluble group represented by general formula (I), (II) or (III) as defined in the specification, and at least one monomer unit derived from monomer compound (B): (meth)acrylate having poly(oxyalkylene) chain. A lithographic printing plate prepared from a presensitized plate having a photosensitive layer of said photosensitive compound of the present invention shows improvement of abrasion resistance, printing durability, chemical resistance, development latitude, and contamination property.
    Type: Application
    Filed: October 5, 2001
    Publication date: June 6, 2002
    Inventors: Kazuo Fujita, Shiro Tan
  • Patent number: 6399267
    Abstract: A radiation sensitive resin composition which can be processed and molded at low temperatures and has resolution, solvent resistance, adhesion to a substrate and storage stability required as an interlaminar insulating film. This radiation sensitive resin composition comprises: (A) a copolymer obtained by copolymerizing (a1) an unsaturated carboxylic acid and/or an unsaturated carboxylic anhydride, (a2) an epoxy compound such as &bgr;-methylglycidyl acrylate and/or an epoxy compound such as a monomer represented by the following formula (3):  and (a3) an olefinic unsaturated compound other than the above (a1) and (a2); and (B) a 1,2-quinonediazide compound.
    Type: Grant
    Filed: June 1, 2000
    Date of Patent: June 4, 2002
    Assignee: JSR Corporation
    Inventors: Isao Nishimura, Masayoshi Suzuki, Fumiko Yonezawa, Masayuki Endo
  • Patent number: 6395447
    Abstract: A resist material having a resist and particles mixed into the resist, a major component of the particles being a cluster of carbon atoms, is provided. A method for fabricating a resist material is also provided, the method repeatedly performing: a first step of coating a substrate with a resist film; and a second step of depositing particles whose major component is a cluster of carbon atoms on the resist film. Accordingly, a resist film with high etching resistance can be obtained, and it is possible to realize a reduction in the thickness of the resist film, improvements of contrast of resist patterns; resist sensitivity; heat resistance of resist films; mechanical strength of resist patterns; and further, stabilization of resist sensitivity. Therefore, highly precise fine pattern fabrication can be realized.
    Type: Grant
    Filed: July 27, 2000
    Date of Patent: May 28, 2002
    Assignee: Nippon Telegraph and Telephone Corporation
    Inventors: Tetsuyoshi Ishii, Toshiaki Tamamura, Hiroshi Nozawa, Kenji Kurihara
  • Publication number: 20020061458
    Abstract: A positive photoresist composition includes (A) an alkali-soluble resin and (B) a photosensitive ingredient, in which the photosensitive ingredient (B) includes an ester of a compound represented by following Formula (I) with a 1,2-naphthoquinonediazidosulfonyl compound: 1
    Type: Application
    Filed: September 12, 2001
    Publication date: May 23, 2002
    Applicant: TOKYO OHKA KOGYO CO., LTD.
    Inventors: Shinichi Hidesaka, Atsushi Sawano
  • Patent number: 6391514
    Abstract: A photosensitive positive working composition suitable for use as a photoresist, which comprises an admixture of at least one film forming resin; at least one photosensitizer; and a photoresist solvent mixture containing more than 50 weight percent of an alkylene glycol alkyl ether and less than 50 weight percent of either an alkyl alkoxy propionate or an alkyl amyl ketone, and a process for producing such a photoresist composition.
    Type: Grant
    Filed: August 18, 2000
    Date of Patent: May 21, 2002
    Assignee: Clariant Finance (BVI) Limited
    Inventors: J. Neville Eilbeck, Alberto D. Dioses
  • Patent number: 6383708
    Abstract: A positive resist composition comprising, in admixture, an alkali-soluble resin, a quinone diazide compound and a mixed solvent of (B) at least one organic solvent selected from the group consisting of &ggr;-butyrolactone, 3-methoxybutanol and cyclohexanone and (A) an organic solvent other than the solvents (B) which does not have simultaneously an alkylcarbonyl group and an alkoxy group in a molecule and has a boiling point of from 140 to 180° C. under atmospheric pressure (B), which composition has a large &ggr;-value and provides an improved profile and a large depth of focus.
    Type: Grant
    Filed: December 2, 1993
    Date of Patent: May 7, 2002
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yasunori Uetani, Yasunori Doi, Kazuhiko Hashimoto, Haruyoshi Osaki, Ryotaro Hanawa
  • Patent number: 6384103
    Abstract: Radiation-sensitive resin composition having excellent and well-balanced various properties required for photoresist, such as sensitivity, pattern profile and heat resistance. The radiation-sensitive resin composition comprises an alkali-soluble resin and a photosensitizer having a quinonediazide group. The alkali-soluble resin is a phenol novolak resin which is treated by a thin film distillation method to selectively remove monomer and dimer. The novolak resin treated by thin film distillation method preferably shows the following ratio in area in its profile in gel permeation chromatography with a detector at 280 nm: B2/B1≧0.95; C2/(A2+B2+C2)≦0.060 wherein A1 is a high-molecular region, B1 is a middle-molecular region, and C1 is a monomer/dimer region before the treatment of the starting novolak resin, and A2, B2 and C2 are the corresponding counterparts after the treatment of the novolak resin.
    Type: Grant
    Filed: December 1, 2000
    Date of Patent: May 7, 2002
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Akio Arano, Kenji Yamamoto
  • Patent number: 6383709
    Abstract: A positive resist composition which gives improved profile without lowering other properties such as sensitivity and resolution, and comprises an alkali-soluble novolak resin, a quinone diazide type radiation-sensitive agent and N-(n-octylsulfonyloxy)succinimide
    Type: Grant
    Filed: March 21, 2001
    Date of Patent: May 7, 2002
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yasunori Uetani, Jun Tomioka, Sang-Ho Lee
  • Patent number: 6379859
    Abstract: Disclosed are a positive photoresist composition including (A) an alkali-soluble resin, (B) a photosensitizer containing a quinonediazide ester of, e.g., bis[2,5-dimethyl-3-(2-hydroxy-5-methylbenzyl)-4-hydroxyphenyl]methane and (C) e.g., 2,6-bis(2,5-dimethyl-4-hydroxybenzyl)-4-methylphenol; and a process including the steps of coating the composition onto a 8 to 12-inch substrate, drying, exposing and developing the same. The composition which can form a pattern having a good shape whose dimensional changes are minimized in a wide range over surface of the substrate, particularly in processes using a large-diameter substrate, and the process for forming a resist pattern using the composition are provided.
    Type: Grant
    Filed: June 1, 1999
    Date of Patent: April 30, 2002
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Takako Suzuki, Sachiko Tamura, Kousuke Doi, Hidekatsu Kohara, Toshimasa Nakayama
  • Patent number: 6376150
    Abstract: An IR- and UV-radiation-sensitive composition comprising a diazo resin, a diazo ester, at least one novolac resin and an IR-ray absorber. A lithographic plate comprising a support coated with the said photosensitive composition.
    Type: Grant
    Filed: May 11, 1999
    Date of Patent: April 23, 2002
    Assignee: Lastra S.p.A.
    Inventors: Angelo Bolli, Paolo Peveri, Andrea Tettamanti
  • Patent number: 6372403
    Abstract: A photosensitive resin composition comprising (a) a photosensitizer having in its structure 1,2-diazidonaphthoquinone structure, and a methylene-bridged structure composed of two or more methyl-substituted phenol derivatives, (b) a polymer having both hydroxyl group and carboxyl group, or a combination of a polymer having hydroxyl group and one having carboxyl group, (c) a crosslinking agent capable of crosslinking hydroxyl group and carboxyl group, and (d) a solvent. This composition can form highly transparent films, and, in addition, patterns having high contrast can be obtained when this composition is used as a photoresist.
    Type: Grant
    Filed: November 15, 2000
    Date of Patent: April 16, 2002
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Minoru Kurisaki, Takamasa Harada, Takanori Kudo, Takashi Takeda, Junichi Fukuzawa
  • Patent number: 6365306
    Abstract: Disclosed are a photosensitive polymer composition comprising (a) a polymer soluble in an aqueous alkaline solution, (b) an o-quinonediazide compound, and (c) a dissolution inhibitor for the component (a) in an aqueous alkaline solution; a method of using the composition for forming relief patterns; and electronic parts having, as a passivating film or an interlayer insulating film, the relief pattern as formed in the method. The composition has high sensitivity, and give fine relief patterns having a good profile.
    Type: Grant
    Filed: February 6, 2001
    Date of Patent: April 2, 2002
    Assignees: Hitachi Chemical DuPont Microsystems L.L.C., Hitachi Chemical Dupont Microsystems Ltd.
    Inventors: Masataka Nunomura, Noriyuki Yamazaki
  • Publication number: 20020012865
    Abstract: Disclosed are a positive photoresist composition including (A) an alkali-soluble resin, (B) a photosensitizer containing a quinonediazide ester of, e.g., bis[2,5-dimethyl-3-(2-hydroxy-5-methylbenzyl)-4-hydroxyphenyl]methane and (C) e.g., 2,6-bis(2,5-dimethyl-4-hydroxybenzyl)-4-methylphenol; and a process including the steps of coating the composition onto a 8 to 12-inch substrate, drying, exposing and developing the same. The composition which can form a pattern having a good shape whose dimensional changes are minimized in a wide range over surface of the substrate, particularly in processes using a large-diameter substrate, and the process for forming a resist pattern using the composition are provided.
    Type: Application
    Filed: June 1, 1999
    Publication date: January 31, 2002
    Inventors: TAKAKO SUZUKI, SACHIKO TAMURA, KOUSUKE DOI, HIDEKATSU KOHARA, TOSHIMASA NAKAYAMA
  • Publication number: 20020012867
    Abstract: A photosensitive resin composition comprises a base resin (e.g., novolak resins, polyvinylphenol-series polymers), a first photoactive ingredient (e.g., diazobenzoquinone derivatives, diazonaphthoquinone derivatives) and a second photoactive ingredient (e.g., mixtures with azide compounds) each having an absorption range at wavelength &lgr;1 or &lgr;2, the wavelengths thereof being different from each other. Between the first and second photoactive ingredients, at least one photoactive ingredient is substantially inert at the absorption wavelength of the other. After exposing the photosensitive resin composition to a light to form a pattern, the whole surface of the photosensitive layer is exposed to a light of the other wavelength to make the surface hardly soluble (in the case a positive pattern is formed) or readily soluble (in the case a negative pattern is formed) in a developer, and developed, thereby forming a pattern of high resolution.
    Type: Application
    Filed: August 18, 1999
    Publication date: January 31, 2002
    Inventor: TOKUGEN YASUDA
  • Publication number: 20020006574
    Abstract: A positive resist composition, having a superior resolution as well as good resist performances such as sensitivity, depth of focus and profile, which comprises a novolac resin, a radiation-sensitive quinonediazide compound and a thioxanthone compound represented by the following formula (I): 1
    Type: Application
    Filed: June 1, 1999
    Publication date: January 17, 2002
    Inventors: YASUNORI UETANI, HIROSHI MORIUMA, YOSHIYUKI TAKATA
  • Patent number: 6338930
    Abstract: A method for preparing a positive photoresist layer is provided. In this method, a photoresist composition is drop-wise applied on an insulator layer or a conductive metal layer formed on a substrate. The photoresist composition includes a polymer resin, a sensitizer for changing solubility of the photoresist layer when exposed and a solvent. The coated substrate is rotated at the speed of 1,250 to 1,350 rpm for 4.2 to 4.8 seconds. The coated substrate is then dried and the dried substrate is exposed to some form of radiation. Next, the exposed portion is removed by using an alkaline developing solution. The solvent preferably includes 3-methoxybutyl acetate and 4-butyrolactone, or includes 3-methoxybutyl acetate, 2-heptanone, and 4-butyrolactone.
    Type: Grant
    Filed: September 5, 2000
    Date of Patent: January 15, 2002
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Jin-Ho Ju, Yu-Kyung Lee, Hong-Sik Park, Yun-Jung Nah, Ki-Soo Kim, Sung-Chul Kang
  • Publication number: 20020001769
    Abstract: A positive photoresist composition includes (A) an alkali-soluble resin, in which part of phenolic hydroxyl groups is protected by an acid-decomposable group; (B) a quinonediazide ester; and (C) a compound which generates an acid upon irradiation of light with a wavelength of 365 nm. This positive photoresist composition can form a fine pattern of about 0.35 &mgr;m in the photolithographic process using i-ray (365 nm), is excellent in focal depth range properties in such an ultrafine region, and has a high sensitivity.
    Type: Application
    Filed: May 24, 2001
    Publication date: January 3, 2002
    Applicant: TOKYO OHKA KOGYO CO., LTD.
    Inventors: Kousuke Doi, Ken Miyagi, Atsuko Hirata, Hidekatsu Kohara, Toshimasa Nakayama
  • Publication number: 20010053493
    Abstract: A positive photoresist composition includes (A) an alkali-soluble resin, (B) a quinonediazide ester of, e.g., bis[2,5-dimethyl-3-(2-hydroxy-5-methylbenzyl)-4-hydroxyphenyl]methane and/or 2,4-bis[4-hydroxy-3-(4-hydroxybenzyl)-5-methylbenzyl]-6-cyclohexylphenol, and (C) 4,4′-bis(diethylamino)benzophenone. The composition exhibits high sensitivity and definition and improved focal depth range properties and underexposure margin.
    Type: Application
    Filed: May 28, 1999
    Publication date: December 20, 2001
    Inventors: TAKAKO SUZUKI, KOUSUKE DOI, HIDEKATSU KOHARA, TOSHIMASA NAKAYAMA
  • Patent number: 6331383
    Abstract: A photosensitive composition comprising a photoacid generator for forming an acid by exposing to far ultraviolet light, a pH indicator coloring so as to exhibit an absorption band at the i-line wavelength region in the presence of the acid, and an i-line photosensitizer chemically changing by exposing to the i-line; and methods for patterning and for manufacturing a semiconductor device using such a photosensitive composition. The photosensitive composition enables etching, fine pattern formation and semiconductor device manufacturing to simplify.
    Type: Grant
    Filed: September 19, 1996
    Date of Patent: December 18, 2001
    Assignee: Canon Kabushiki Kaisha
    Inventor: Keita Sakai
  • Publication number: 20010051313
    Abstract: A positive resist composition which gives improved profile without lowering other properties such as sensitivity and resolution, and comprises an alkali-soluble novolak resin, a quinone diazide type radiation-sensitive agent and N-(n-octylsulfonyloxy) succinimide
    Type: Application
    Filed: March 21, 2001
    Publication date: December 13, 2001
    Inventors: Yasunori Uetani, Jun Tomioka, Sang-Ho Lee
  • Patent number: 6329110
    Abstract: A positive-type, heat-resistant photosensitive polymer composition comprising (a) a polyimide precursor or a polyimide which is soluble in an aqueous alkaline solution, (b) a compound capable of generating an acid when exposed to light, and (c) a compound having a phenolic hydroxyl group; a method of forming a relief pattern comprising a step of applying the composition onto a substrate and drying it thereon, a step of exposing it, a step of developing it, and a step of heating it; and an electronic part having as a surface-protecting film or an interlayer insulating film.
    Type: Grant
    Filed: November 1, 1999
    Date of Patent: December 11, 2001
    Assignees: Hitachi Chemical DuPont Microsystems LTD, Hitachi Chemical DuPont Microsystems LLC
    Inventors: Masataka Nunomura, Masayuki Ohe
  • Patent number: 6326122
    Abstract: A positive photosensitive composition showing a difference in solubility in an alkali developer as between an exposed portion and a non-exposed portion, which comprises, as components inducing the difference in solubility, (a) a photo-thermal conversion material, and (b) a high molecular compound, of which the solubility in an alkali developer is changeable mainly by a change other than a chemical change.
    Type: Grant
    Filed: August 5, 1997
    Date of Patent: December 4, 2001
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Hideki Nagasaka, Akihisa Murata
  • Publication number: 20010044065
    Abstract: Multilayer photoimageable elements, useful for forming lithographic printing members, are disclosed. The elements comprise a support, a top layer, and a chemical resistant underlayer. The underlayer is resistant to aggressive washes, such as a UV wash. In one embodiment, the underlayer comprises a copolymer of N-substituted maleimide, methacrylamide, and methacrylic acid. A process for preparing a lithographic printing member is also disclosed.
    Type: Application
    Filed: December 5, 2000
    Publication date: November 22, 2001
    Inventors: Celin-Savariar Hauck, Gerhard Hauck
  • Publication number: 20010044066
    Abstract: A resist composition comprising (A) an alkali-insoluble or substantially insoluble polymer having acidic functional groups protected with acid labile groups, which polymer becomes alkali-soluble upon elimination of the acid labile groups, (B) a photoacid generator, and (C) a 1,2-naphthoquinonediazidosulfonyl group-bearing compound has a high resolution and sensitivity, and provides resist patterns of excellent plating resistance when used in UV lithography at an exposure light wavelength of at least 300 nm.
    Type: Application
    Filed: April 17, 2001
    Publication date: November 22, 2001
    Applicant: Shin-Etsu Chemical Co., Ltd.
    Inventors: Hideto Kato, Kazuhiro Nishikawa, Yoshinori Hirano, Katsuya Takemura
  • Publication number: 20010041299
    Abstract: The present invention relates to a positiive-working presensitized plate useful for preparing a lithographic printing plate comprising a positive-working photosensitive composition comprising at least one ester of 1,2-naphthoquinone-2-diazide-5-sulfonic acid, at least one ester of 1,2-naphthoquinone-2-diazide-4-sulfonic acid, and at least one polymer which is insoluble in water and soluble in an aqueous alkaline solution and which comprises at least one group or bond selected from sulfonamide group, urea bond or urethane bond. A lithographic printing plate prepared from the presensitized plate of the present invention shows improvement of chemical-resistance and printing durability, and good sensitivity, coupling property, adaptability to ball-point pen, shelf stability, and stability of sensitivity with time after exposure.
    Type: Application
    Filed: March 20, 2001
    Publication date: November 15, 2001
    Inventors: Kazuo Fujita, Shiro Tan, Akira Nagashima
  • Publication number: 20010038965
    Abstract: From a heat-curable photosensitive composition comprising a cresol and/or xylenol novolac resin which has been partially 1,2-naphthoquinonediazido-4- or 5-sulfonate esterified and having a weight average molecular weight of 1,000-10,000, an epoxy compound, and a solvent therefor, a pattern featuring improved solvent resistance and heat resistance can be formed at a high sensitivity and resolution by a simple process. The pattern is suitable as an interlayer insulating film for use in thin-film magnetic heads.
    Type: Application
    Filed: February 15, 2001
    Publication date: November 8, 2001
    Inventors: Takafumi Ueda, Kenji Araki, Hideto Kato
  • Patent number: 6312863
    Abstract: A positive photoresist composition includes (A) an alkali-soluble resin, and (B) a photosensitizer including an ester of a 1,2-naphthoquinonediazidesulfonyl compound with a compound of the following formula (I). This positive photoresist composition has satisfactory sensitivity, definition, and depth of focus properties, can form both dense patterns and isolation patterns with good shapes in the formation of mixed resist patterns, and can minimize inverted taper shape formation of isolation resist patterns induced by shifts of focal depth to the minus side.
    Type: Grant
    Filed: July 18, 2000
    Date of Patent: November 6, 2001
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Shinichi Hidesaka, Atsushi Sawano, Kousuke Doi, Hidekatsu Kohara, Toshimasa Nakayama
  • Publication number: 20010031419
    Abstract: A positive-type, heat-resistant photosensitive polymer composition comprising (a) a polyimide precursor or a polyimide which is soluble in an aqueous alkaline solution, (b) a compound capable of generating an acid when exposed to light, and (c) a compound having a phenolic hydroxyl group; a method of forming a relief pattern comprising a step of applying the composition onto a substrate and drying it thereon, a step of exposing it, a step of developing it, and a step of heating it; and an electronic part having as a surface-protecting film or an interlayer insulating film.
    Type: Application
    Filed: March 30, 2001
    Publication date: October 18, 2001
    Inventors: Masataka Nunomura, Masayuki Ohe
  • Patent number: 6300033
    Abstract: In a positive photoresist composition including (A) an alkali-soluble resin and (B) a photosensitizer, Ingredient (B) contains (B-1) a quinonediazide ester of, e.g., bis[2,5-dimethyl-3-(2-hydroxy-5-methylbenzyl)-4-hydroxyphenyl]methane or 2,4-bis[4-hydroxy-3-(4-hydroxybenzyl)-5-methylbenzyl]-6-cyclohexylphenol, and (B-2) a quinonediazide ester of, e.g., methyl gallate or 2,2-bis(2,3,4-trihydroxyphenyl)propane. The composition exhibits high sensitivity and definition, and improved focal depth range properties and underexposure margin.
    Type: Grant
    Filed: May 26, 1999
    Date of Patent: October 9, 2001
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Takako Suzuki, Kousuke Doi, Hidekatsu Kohara, Toshimasa Nakayama
  • Publication number: 20010026905
    Abstract: A positive resist composition, having a superior resolution as well as good resist performances such as sensitivity, depth of focus and profile, is described and includes a novolac resin, a radiation-sensitive quinonediazide compound and a thioxanthone compound represented by the following formula (I): 1
    Type: Application
    Filed: February 23, 2001
    Publication date: October 4, 2001
    Applicant: Sumitomo Chemical Company, Limited
    Inventors: Yasunori Uetani, Hiroshi Moriuma, Yoshiyuki Takata
  • Patent number: 6296982
    Abstract: An imagable composition, for example a coating on a lithographic printing plate, comprises a carboxylic acid derivative of a cellulosic polymer and a diazide moiety, and may be imaged in various ways, including by ultra-violet radiation, by infra-red radiation and by heat. The presence of the cellulosic polymer can act to enhance resistance to certain organic liquids and/or to increase operating speed.
    Type: Grant
    Filed: November 19, 1999
    Date of Patent: October 2, 2001
    Assignee: Kodak Polychrome Graphics LLC
    Inventors: Michael Yates, Carolyn O'Sullivan, Gerhard Hauck
  • Patent number: 6296992
    Abstract: A positive photoresist composition for forming a contact hole which comprises (A) an alkali-soluble resin; (B) a naphthoquinonediazide group-containing compound; and (C) a solvent, wherein the ingredient (B) comprises: at least one naphthoquinonediazidesulfonic ester of a polyphenol compound, where said polyphenol compound is composed of from 4 to 6 benzene rings each bonding via a methylene chain, each of the methylene chains is in a meta position to other methylene chains, and each of the benzene rings has a hydroxyl group is provided. According to tie present invention, a positive photoresist composition and a process for forming a contact hole can be provided each of which gives a contact hole pattern image in exact accordance with a mask pattern without dimple formation, in the contact hole forming technologies using the phaseshift method.
    Type: Grant
    Filed: March 31, 2000
    Date of Patent: October 2, 2001
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Masaki Kurihara, Satoshi Niikura, Miki Kobayashi, Kousuke Doi, Hidekatsu Kohara, Toshimasa Nakayama
  • Publication number: 20010024762
    Abstract: A phenol novolak resin has a peak intensity ratio of ortho-ortho bond (o-o)/ortho-para bond (o-p)/para-para bond (p-p) in a resin structure not substantially varying in each molecular weight fraction and has a weight average molecular weight (Mw) of 3000 to 20000 in terms of polystyrene, which peak intensity ratio is detected by 13C-NMR analysis. The phenol novolak resin can form both dense pattern and isolation pattern with good shapes in the formation of a fine resist pattern of not more than 0.35 &mgr;m and has satisfactory sensitivity, definition, and focal depth range properties, and has a resin composition being uniform in each molecular weight fraction. A process for producing the phenol novolak resin, and a positive photoresist composition using the resin are also provided.
    Type: Application
    Filed: February 28, 2001
    Publication date: September 27, 2001
    Inventors: Ken Miyagi, Yasuhide Ohuchi, Atsuko Hirata, Kousuke Doi, Hidekatsu Kohara, Toshimasa Nakayama
  • Publication number: 20010019808
    Abstract: A single layer lift-off resist composition comprising a novolac resin, a quinonediazidosulfonate photosensitive agent, and an aromatic hydroxy compound having at least one phenolic hydroxyl group in which the phenolic hydroxyl group is partially acylated is improved in adhesion to a substrate.
    Type: Application
    Filed: February 22, 2001
    Publication date: September 6, 2001
    Inventors: Kazumi Noda, Tomoyoshi Furihata, Hideto Kato
  • Patent number: 6284439
    Abstract: A photoresist having both positive and negative tone components resulting in a lower “k” factor than the single tone photoresist is disclosed. The hybrid resist may either have the negative tone resist or the positive tone resist as the major portion, while the other tone is a relatively minor portion. For examples, a positive tone resist may include a minor portion of a negative tone cross-linker or a negative tone resist may include positively acting functional groups. The hybrid resist of the present invention allows for wider exposure dosage windows, therefore increasing the yield or performance and line is density.
    Type: Grant
    Filed: June 30, 1998
    Date of Patent: September 4, 2001
    Assignee: International Business Machines Corporation
    Inventors: Steven J. Holmes, Ahmad D. Katnani, Niranjan M. Patel, Paul A. Rabidoux
  • Publication number: 20010018160
    Abstract: A positive resist composition contains (A) a novolak resin having a weight average molecular weight calculated as polystyrene of 2,000-20,000 wherein 2.5-27 mol % of the hydrogen atom of a hydroxyl group is replaced by a 1,2-naphthoquinonediazidosulfonyl group and (B) a low molecular aromatic compound having phenolic hydroxyl groups and 2-20 benzene rings wherein the ratio of the number of phenolic hydroxyl groups to the number of benzene rings is between 0.5 and 2.5. By forming a resist layer on a substrate from the positive resist composition and baking the resist layer at 90-130° C., followed by exposure and development, there is formed a resist pattern having an undercut of desired configuration. Owing to high resolution and improved dimensional control, heat resistance and film retention, the resist pattern lends itself to a lift-off technique.
    Type: Application
    Filed: February 14, 2001
    Publication date: August 30, 2001
    Applicant: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takafumi Ueda, Hideto Kato, Toshihiko Fujii, Miki Kobayashi
  • Patent number: 6274287
    Abstract: A positive resist composition excellent in resolution, having a good balance with other performances required to resists and comprising an alkali-soluble resin, a radiation-sensitive ingredient and a hydroxyphenyl ketone compound represented by the following formula (I): wherein R1, R2, R3, R4 and R5 independently represent hydrogen, alkyl or alkoxy and n represents an integer of 1 to 3 is provided.
    Type: Grant
    Filed: June 22, 2000
    Date of Patent: August 14, 2001
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Hiroshi Moriuma, Yoshiyuki Takata
  • Patent number: 6270939
    Abstract: A radiation-sensitive resin composition comprising a solution of an alkali-soluble resin and a radiation-sensitive compound in a solvent comprising a monooxymonocarboxylic acid ester. This composition has a high storage stability (i.e., a very small amount of fine particles are formed during storage) and is suited for use as a resist for making integrated circuits.
    Type: Grant
    Filed: August 16, 2000
    Date of Patent: August 7, 2001
    Assignee: JSR Corporation
    Inventors: Yoshihiro Hosaka, Ikuo Nozue, Masashige Takatori, Yoshiyuki Harita
  • Publication number: 20010009746
    Abstract: Disclosed are a photosensitive polymer composition comprising (a) a polymer soluble in an aqueous alkaline solution, (b) an o-quinonediazide compound, and (c) a dissolution inhibitor for the component (a) in an aqueous alkaline solution; a method of using the composition for forming relief patterns; and electronic parts having, as a passivating film or an interlayer insulating film, the relief pattern as formed in the method. The composition has high sensitivity, and give fine relief patterns having a good profile.
    Type: Application
    Filed: February 6, 2001
    Publication date: July 26, 2001
    Inventors: Masataka Nunomura, Noriyuki Yamazaki
  • Patent number: 6265129
    Abstract: Improved positive photosensitive composition for application of the lift-off technique comprises (A) an alkali-soluble resin and (B) a mixture of two photosensitive agents in admixture with the alkali-soluble resin, one being (i) a photosensitive agent which shows the tendency to form a resist pattern of a feature profile having a micro-groove upon exposure and the other being (ii) a photosensitive agent which does not show the stated tendency but shows the tendency to form a resist pattern having a rectangular or tapered cross-sectional feature profile upon exposure and using the composition, one can form half-a-micron meter and even finer conducting patterns, electrodes or insulation patterns in a highly reproducible manner.
    Type: Grant
    Filed: November 7, 1997
    Date of Patent: July 24, 2001
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Koichi Takahashi, Tetsuya Kato, Tomosaburo Aoki
  • Publication number: 20010006752
    Abstract: A resist composition comprising, in a resist, an additive which has a melting point of 160° C. or above, contains no aromatic ring, has a molecular size of no greater than 50 Å and is soluble in the developing solution for the resist, at 1-50 parts by weight with respect to 100 parts by solid weight of the resist, as well as a pattern forming process employing it. It thereby becomes possible to obtain high-resolution resist patterns.
    Type: Application
    Filed: April 9, 1999
    Publication date: July 5, 2001
    Applicant: FUJITSU LIMITED
    Inventors: KEIJI WATANABE, MIWA KOZAWA, EI YANO, TAKAHISA NAMIKI, KOJI NOZAKI, JUNICHI KON, EIICHI HOSHINO, MASAHIRO URAGUCHI, TOSHIKATSU MINAGAWA, YUICHI YAMAMOTO
  • Patent number: 6245478
    Abstract: A resist composition exhibiting an improved profile performance without impairing the resolution, the sensitivity, etc. which comprises a binder component; a radiation-sensitive component; and a succinimide compound represented by the following formula (I): wherein Q1 represents an alkyl group which may be optionally substituted with alkoxy, halogen or nitro, an alicyclic hydrocarbon residue, an aryl group, or an aralkyl group; and Q2, which may be the same as or different from Q1, represents hydrogen, an alkyl group which may be optionally substituted with alkoxy, halogen or nitro, an alicyclic hydrocarbon residue, an aryl group, or an aralkyl group.
    Type: Grant
    Filed: September 17, 1999
    Date of Patent: June 12, 2001
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yasunori Uetani, Ichiki Takemoto
  • Patent number: 6232032
    Abstract: Disclosed are a photosensitive polymer composition comprising (a) a polymer soluble in an aqueous alkaline solution, (b) an o-quinonediazide compound, and (c) a dissolution inhibitor for the component (a) in an aqueous alkaline solution; a method of using the composition for forming relief patterns; and electronic parts having, as a passivating film or an interlayer insulating film, the relief pattern as formed in the method. The composition has high sensitivity, and give fine relief patterns having a good profile.
    Type: Grant
    Filed: May 27, 1999
    Date of Patent: May 15, 2001
    Assignees: Hitachi Chemical DuPont Microsystems L.L.C., Hitachi Chemical DuPont Microsystems Ltd.
    Inventors: Masataka Nunomura, Noriyuki Yamazaki
  • Patent number: 6232031
    Abstract: A positive-working, infrared imageable coating and a lithographic printing plate or other element with the coating are described. The coating is a phenolic resin containing an o-diazonaphthoquinone derivative which couples or reacts with the resin to partially insolubilize the coating and an infrared absorbing dye or pigment which further insolubilizes the coating and which renders the coating imageable by infrared radiation. The coating contains only that quantity of infrared radiation absorber necessary to be imageable and only that small quantity of o-diazonaphthoquinone derivative necessary to supplement the insolubilizing function of the absorber. Specifically, the absorber is from 1 to 10 weight percent of the total dry weight of the coating and the dry weight ratio of the absorber to the diazonaphthoquinone moiety is greater than 1:5 and preferably 1:2 or greater.
    Type: Grant
    Filed: March 30, 2000
    Date of Patent: May 15, 2001
    Assignee: Ano-Coil Corporation
    Inventors: Robert F. Gracia, Yijin Ren, William J. Rozell, Howard A. Fromson
  • Patent number: 6228554
    Abstract: A radiation-sensitive resin composition comprising a solution of an alkali-soluble resin and a radiation-sensitive compound in a solvent comprising a monooxymono-carboxylic acid ester. This composition has a high storage stability (i.e., a very small amount of fine particles are formed during storage) and is suited for use as a resist for making integrated circuits.
    Type: Grant
    Filed: October 8, 1999
    Date of Patent: May 8, 2001
    Assignee: JSR Corporation
    Inventors: Yoshihiro Hosaka, Ikuo Nozue, Masashige Takatori, Yoshiyuki Harita
  • Patent number: 6228552
    Abstract: A photosensitive material, which comprises, an alkali-soluble resin moiety having an alicyclic skeleton, a polycyclic condensation skeleton, or both alicyclic and polycyclic condensation skeletons, and a diazo compound moiety. The diazo compound moiety may be contained in a side chain of the alkali-soluble resin moiety or included in the photosensitive material in separate from the alkali-soluble resin moiety.
    Type: Grant
    Filed: September 10, 1997
    Date of Patent: May 8, 2001
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Takeshi Okino, Koji Asakawa, Naomi Shida, Toru Ushirogouchi, Makoto Nakase
  • Patent number: 6218069
    Abstract: A photosensitive resin composition contains a photosensitive resin comprising recurring units of formula (1) and having a Mw of 1,300-11,000 and 20-5,000 ppm of a tertiary amine compound of formula (2). R is hydrogen or a 1,2-naphthoquinonediazido-5-sulfonic acid residue, the content of 1,2-naphthoquinonediazido-5-sulfonic acid residue in R is 3-27 mol %, and m is a number from 0 to 3, X is a C6-20 alkyl, aryl or aralkyl group, Y and Z each are a C1-20 alkyl group. The composition is improved in sensitivity stability and adhesion to substrates and eliminates the risk of causing corrosion of metal substrates.
    Type: Grant
    Filed: January 10, 2000
    Date of Patent: April 17, 2001
    Assignee: Shin-Etsu Chemical Co. Ltd.
    Inventors: Hideto Kato, Tomoyoshi Furihata, Satoshi Okazaki
  • Patent number: 6218083
    Abstract: A method for producing a predetermined resist pattern on e.g. a lithographic printing plate, circuit board or mask comprises the imagewise exposure of a radiation sensitive diazide-containing coating (conventionally considered as a UV sensitive material), to non-UV radiation, such as direct heat radiation or infra-red radiation. A positive of the exposed image is revealed on development. Additionally, it has been found that a flood exposure to UV radiation after the imagewise exposure to the non-UV radiation means that a negative of the exposed image is revealed, on development.
    Type: Grant
    Filed: March 5, 1999
    Date of Patent: April 17, 2001
    Assignee: Kodak Plychrome Graphics, LLC
    Inventors: Christopher D. McCullough, Kevin B. Ray, Alan S. Monk, Stuart Bayes, Anthony P. Kitson
  • Patent number: RE37179
    Abstract: A radiation sensitive resin composition which comprises (A) a polymer which becomes alkali-soluble in the presence of an acid and (B) a radiation sensitive acid generator which generates an acid upon irradiation with a radiation, said polymer (A) comprising two recurring units represented by the general formulas (1) and (2) and a recurring unit which acts to reduce the solubility of the polymer is an alkali developer after the irradiation: wherein R1 represents a hydrogen atom or a methyl group and R2 represents a hydrogen atom or a methyl group. Said composition provides a chemically amplified positive resist which can give a fine pattern with a good pattern shape, and said resist is freed from volume shrinkage, peeling failure and adhesive failure, is excellent in dry etching resistance and effectively reacts with various radiations to give a good pattern shape which is excellent in photolithographic process stability, said pattern shape having no thinned portion at the upper part.
    Type: Grant
    Filed: October 21, 1999
    Date of Patent: May 15, 2001
    Assignee: JSR Corporation
    Inventors: Mikio Yamachika, Eiichi Kobayashi, Akira Tsuji, Toshiyuki Ota