O-quinone Diazide Patents (Class 430/193)
  • Publication number: 20030134223
    Abstract: A composition includes (A) a novolak resin containing at least 20% by mole of a m-cresol repeating unit and having a 1-ethoxyethyl group substituting for part of hydrogen atoms of phenolic hydroxyl groups, (B) a quinonediazide ester of, for example, the following formula, and (C) 1,1-bis(4-hydroxyphenyl)cyclohexane.
    Type: Application
    Filed: November 15, 2002
    Publication date: July 17, 2003
    Applicant: TOKYO OHKA KOGYO CO., LTD.
    Inventors: Akira Katano, Yusuke Nakagawa, Shinichi Kono, Kousuke Doi
  • Patent number: 6593043
    Abstract: A composition of a positive photosensitive resin precursor includes (a) a polyamic acid ester and/or a polyamic acid each having at least one selected from a carboxyl group, a phenolic hydroxyl group, a sulfonic acid group and a thiol group at the end of a principal chain of the polymer, (b) a compound having a phenolic hydroxyl group, and (c) a quinonediazide sulfnate. The composition can be subjected to dissolution in an alkaline developer.
    Type: Grant
    Filed: November 1, 2001
    Date of Patent: July 15, 2003
    Assignee: Toray Industries, Inc.
    Inventors: Mitsuhito Suwa, Kazuto Miyoshi, Masao Tomikawa
  • Publication number: 20030108822
    Abstract: A method of forming a minute resist pattern wherein a positive-working photoresist composition containing 3 to 15 parts by weight of a quinone diazide group-containing photosensitizer relative to 100 parts by weight of alkali-soluble novolak resin is developed by an aqueous organic or inorganic alkali solution having a lower alkali concentration than that of the conventional one as the developer. The preferable example of the organic alkali materials in the developer is quaternary ammonium hydroxide, and the preferable example of the inorganic alkali materials in the developer is alkali metal hydroxide. The concentrations of the quaternary ammonium hydroxide and the alkali metal hydroxide in the developing solution are 2.2% by weight or less and 0.4% by weight or less respectively. Using such developing solution, high sensitivity, a high film retention rate, high resolution, low process dependency of dimension accuracy, and a formation of excellent pattern profile can be achieved.
    Type: Application
    Filed: December 18, 2002
    Publication date: June 12, 2003
    Applicant: Clariant Finance (BVI) Limited
    Inventors: Akihiko Igawa, Jun Ikemoto
  • Patent number: 6576381
    Abstract: The present invention alleviates the operational problems in production of flip chips and provides a semiconductor device superior in various reliabilities. The preset invention lies in an encapsulated semiconductor device comprising: (a) a polybenzoxazole resin film for chip protection, obtained by coating, on a circuit-formed chip, a positive photosensitive resin composition comprising 100 parts by weight of a polyamide and 1 to 100 parts by weight of a photosensitive diazoquinone compound, and subjecting the coated composition to patterning and curing, and (b) a bump electrode.
    Type: Grant
    Filed: August 10, 2001
    Date of Patent: June 10, 2003
    Assignee: Sumitomo Bakelite Co., Ltd.
    Inventors: Takashi Hirano, Kagehisa Yamamoto, Toshio Banba, Hiroaki Makabe
  • Patent number: 6566031
    Abstract: A positive photoresist composition includes (A) an alkali-soluble resin, (B) a photosensitizer including, for example, a quinonediazide ester of bis[2,5-dimethyl-3-(2-hydroxy-5-methylbenzyl)-4-hydroxyphenyl]methane, and (C) a compound having a gram absorption coefficient of 5 to 60 with respect to light with a wavelength of 365 nm.
    Type: Grant
    Filed: September 26, 2000
    Date of Patent: May 20, 2003
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Takako Suzuki, Kousuke Doi, Hidekatsu Kohara, Toshimasa Nakayama
  • Patent number: 6558867
    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: Grant
    Filed: February 22, 2001
    Date of Patent: May 6, 2003
    Assignee: Shin Etsu Chemical Co., Ltd.
    Inventors: Kazumi Noda, Tomoyoshi Furihata, Hideto Kato
  • Patent number: 6558872
    Abstract: Imagable precursors for masks and for electronic parts comprise a polymeric layer applied to a substrate. The layer comprises at least one polymer having infra-red absorbing groups carried as pendent groups on the polymer backbone. Certain infra-red absorbing groups may also act to insolubilize the polymer in a developer, until it is imagewise exposed to infra-red radiation. Imagewise application of heat, resulting from imagewise exposure of the precursor to infra-red radiation, renders the polymer layer more soluble in the developer than prior to exposure to the infra-red radiation.
    Type: Grant
    Filed: September 9, 2000
    Date of Patent: May 6, 2003
    Assignee: Kodak Polychrome Graphics LLC
    Inventors: Kevin Barry Ray, Anthony Paul Kitson, Eduard Kottmair, Hans-Horst Glatt, Stefan Hilgart
  • Patent number: 6551755
    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: This positive photoresist composition can form a resist pattern mixture including both a dense pattern and an isolation pattern with good shapes and can especially minimize the formation of a back taper shape of an isolation pattern induced by shift of the focus to the minus side.
    Type: Grant
    Filed: September 12, 2001
    Date of Patent: April 22, 2003
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Shinichi Hidesaka, Atsushi Sawano
  • Publication number: 20030059706
    Abstract: A positive photoresist composition includes an alkali-soluble novolak resin(A), an alkali-soluble acrylic resin (B) and a quinonediazido-group-containing compound (C) and is used for the formation of a thick film 5 to 100 &mgr;m thick. The ingredient (B) includes 30% to 90% by weight of a unit (b1) derived from a polymerizable compound having an ether bond and 2% to 50% by weight of a unit (b2) derived from a polymerizable compound having a carboxyl group. The composition is applied on a substrate and thereby yields a photoresist film. Likewise, the composition is applied onto a substrate on an electronic part, is patterned, is plated and thereby yields bumps.
    Type: Application
    Filed: March 5, 2002
    Publication date: March 27, 2003
    Applicant: TOKYO OHKA KOGYO CO., LTD.
    Inventors: Kouichi Misumi, Koji Saito, Toshiki Okui, Hiroshi Komano
  • Patent number: 6537719
    Abstract: A radiation sensitive resin composition which contains a specific amount of a fluorescent material and has high sensitivity, high resolution, excellent highly normalized film remaining characteristics, and capability to form a good pattern. In the case that the radiation sensitive resin composition comprises at least both a resin and a photosensitive material, such as an alkali-soluble novolak resin and a quinonediazide compound, the fluorescent material is used in an amount of 0.0001 to 1.0 parts by weight relative to 100 parts by weight of the photosensitive material. In the case that the radiation sensitive resin composition comprises at least both a resin and a photoacid generator, such as a positive-working or negative-working chemically amplified resist, the fluorescent material is used in an amount of 1.0 to 30.0 parts by weight relative to 100 parts by weight of the photoacid generator.
    Type: Grant
    Filed: October 13, 2000
    Date of Patent: March 25, 2003
    Assignee: Clariant Finance (BVI) Limited
    Inventor: Shuichi Takahashi
  • Publication number: 20030054283
    Abstract: The present invention provides a positive photoresist composition including (A) an alkali-soluble resin and (B) a photosensitizer, and the ingredient (B) is a quinonediazide ester of, for example, 2,6-bis[4-hydroxy-3-(2-hydroxy-3,5-dimethylbenzyl)-2,5-dimethylbenzyl]-4-methylphenol, where the average degree of esterification of 20% to 80%.
    Type: Application
    Filed: July 31, 2002
    Publication date: March 20, 2003
    Applicant: TOKYO OHKA KOGYO CO., LTD.
    Inventors: Satoshi Shimatani, Ken Miyagi, Satoshi Niikura, Hidekatsu Kohara, Toshimasa Nakayama
  • Publication number: 20030054282
    Abstract: A negative-working lithographic printing plate has a coating which is imaged by heating an area of the coating with an infrared laser and actinically reacting the coating in the heated area with ultraviolet or visible radiation. The coating contains an infrared absorber but the coating is not imageable by infrared radiation or by the heat generated. The imaging time is reduced since the actinic reaction rate is increased at the elevated temperature.
    Type: Application
    Filed: September 16, 2002
    Publication date: March 20, 2003
    Inventors: Howard A. Fromson, William J. Rozell
  • Patent number: 6534235
    Abstract: photosensitive resin composition of the present invention is prepared by adding inorganic particles having a functional group and a mean particle size smaller than the wavelength of light for exposure (e.g., about 1 to 100 nm) to a photosensitive resin. The inorganic particles can be of colloidal silica having a functional group. The photosensitive resin composition may be of positive or negative type, and developable with water or an alkali. The amount of the inorganic particles to be used is, relative to 100 parts by weight of the photosensitive resin, about 10 to 500 parts by weight on a solid matter basis. The use of such photosensitive resin composition makes it possible to largely improve oxygen plasma resistance, heat resistance, dry etching resistance, sensitivity, and resolution utilizing a conventional resist or lithography technique.
    Type: Grant
    Filed: October 31, 2000
    Date of Patent: March 18, 2003
    Assignee: Kansai Research Institute, Inc.
    Inventors: Makoto Hanabata, Tokugen Yasuda
  • Patent number: 6525152
    Abstract: Copolymers useful in radiation-sensitive layers of printing plates have the units A, B and C wherein unit A is present in an amount of 5 to a maximum of 50 mol % and R1 and R4 are selected such that the homopolymer of A is alkali-soluble, B is present in an amount of 20-70 mol % and R2, R6 and R7 are selected such that the homopolymer of B has a high glass transition temperature, and C is present in an amount of 10-50 mol % and R3 and R5 are selected such that the homopolymer of C is water-soluble and that unit A is different from unit C.
    Type: Grant
    Filed: August 2, 2000
    Date of Patent: February 25, 2003
    Assignee: Kodak Polychrome Graphics LLC
    Inventor: Mathias Jarek
  • Patent number: 6524764
    Abstract: The present invention relates to a positive type photosensitive resin precursor composition which is characterized in that it contains polymer having, as its chief component, structural units represented by the following general formula (1) and, furthermore, in that it satisfies the following conditions (a) and/or (b). The invention provides an alkali-developable photosensitive composition. (a) There is included an ester of a naphthoquinone diazide sulphonic acid and a phenol compound of dipole moment 0.1 to 1.
    Type: Grant
    Filed: January 29, 2001
    Date of Patent: February 25, 2003
    Assignee: Toray Industries, Inc.
    Inventors: Masao Tomikawa, Mitsuhito Suwa, Yoji Fujita
  • Patent number: 6517988
    Abstract: A radiation-sensitive composition, positive-working coating compositions useful for the preparation of lithographic printing plates and lithographic printing plate precursors comprising the composition are disclosed. The composition comprises at least one quinonediazide compound and at least one carboxylic copolymer. The compositions produce lithographic printing plates that show high print run stability.
    Type: Grant
    Filed: July 12, 2001
    Date of Patent: February 11, 2003
    Assignee: Kodak Polychrome Graphics LLC
    Inventors: Gerhard Hauck, Mathias Jarek
  • Patent number: 6517987
    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: Grant
    Filed: March 20, 2001
    Date of Patent: February 11, 2003
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kazuo Fujita, Shiro Tan, Akira Nagashima
  • Patent number: 6514656
    Abstract: The present invention relates to a positive type image forming material comprising A: an alkali-aqueous-solution-soluble polymer compound having a phenolic hydroxyl group, B: a light and heat decomposing compound which suppresses alkali-aqueous-solution-solubility of said alkali-aqueous-solution-soluble polymer compound (A) having a phenolic hydroxyl group and is decomposed by light or heat to lose its alkali-aqueous-solution-solubility-suppressing effect on said compound (A), and C: a cross-linkable compound which increases said solubility-suppressing effect of said compound (B) when used together with said component (B) in a composition containing the alkali-aqueous-solution-soluble polymer compound (A) having a phenolic hydroxyl group, and which has in its molecule two or more cross-linkable groups which are cross-linked with the alkali-aqueous-solution-soluble polymer compound (A) with heating.
    Type: Grant
    Filed: November 27, 1998
    Date of Patent: February 4, 2003
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Ippei Nakamura, Kazuto Kunita
  • Patent number: 6514676
    Abstract: A method of forming a minute resist pattern wherein a positive-working photoresist composition containing 3 to 15 parts by weight of a quinone diazide group-containing photosensitizer relative to 100 parts by weight of alkali-soluble novolak resin is developed by an aqueous organic or inorganic alkali solution having a lower alkali concentration than that of the conventional one as the developer. The preferable example of the organic alkali materials in the developer is quaternary ammonium hydroxide, and the preferable example of the inorganic alkali materials in the developer is alkali metal hydroxide. The concentrations of the quaternary ammonium hydroxide and the alkali metal hydroxide in the developing solution are 2.2% by weight or less and 0.4% by weight or less respectively. Using such developing solution, high sensitivity, a high film retention rate, high resolution, low process dependency of dimension accuracy, and a formation of excellent pattern profile can be achieved.
    Type: Grant
    Filed: August 1, 2000
    Date of Patent: February 4, 2003
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Akihiko Igawa, Jun Ikemoto
  • Patent number: 6514658
    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: March 30, 2001
    Date of Patent: February 4, 2003
    Assignees: Hitachi Chemical DuPont MicroSystems, Ltd., Hitachi Chemical DuPont MicroSystems, L.L.C.
    Inventors: Masataka Nunomura, Masayuki Ohe
  • Patent number: 6512087
    Abstract: Disclosed is a method for producing low molecular weight oligomers of a film forming resin, which involves: a) providing a solution of the film forming resin in a first solvent system comprising a photoresist solvent, and optionally a water-soluble organic solvent; b) providing a second solvent system comprising at least one substantially pure C5-C8 alkane and/or at least one aromatic compound having at least one hydrocarbyl substituent and/or water/C1-C4 alcohol mixture; and performing steps c)-e) in the following order: c) mixing the solutions from a) and second solvent system from b) in a static mixer for a time period sufficient for efficient mixing; d) feeding the mixture from c) and second solvent system from b) through two separate inlet ports into a liquid/liquid centrifuge, one of the inlet ports feeding the mixture from c), the second inlet port feeding the second solvent system from b) into said liquid/liquid centrifuge at a feed ratio of the mixture from c) to the second solvent system from b) of
    Type: Grant
    Filed: October 27, 2000
    Date of Patent: January 28, 2003
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Stanley F. Wanat, M. Dalil Rahman, Zhong Xiang
  • Patent number: 6503682
    Abstract: A positive photoresist composition having improved sensitivity and resolution, a method of making the composition, and a method for forming a pattern during semiconductor processing using the composition are disclosed. The photoresist composition includes: (i) a photosensitive material obtained by mixing a first photosensitive compound represented by formula (1) and a second photosensitive compound represented by formulae (2a) or (2b); (ii) a resin; and (iii) a solvent. The invention enables the formation of patterns with an exceptional profile due to a high degree of sensitivity and resolution of the photoresist composition.
    Type: Grant
    Filed: March 30, 2000
    Date of Patent: January 7, 2003
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Young Ho Kim, Hoe Sik Chung, Sang Mun Chon, Boo Sup Lee
  • Publication number: 20030003388
    Abstract: A radiation sensitive resin composition containing an alkali soluble resin and a quinonediazide group-containing photosensitizer, in which the photosensitizer comprises a mixture of two or more esters between tetrahydroxybenzophenone and 1,2-naphthoquinonediazidesulfonic acid having different esterification rates. As the photosensitizer, a mixture of photosensitizer A comprising an esterification product from tetrahydroxybenzophenone and 1,2-naphthoquinonediazide-5-sulfonic acid having an average esterification rate of X% (50≦X≦100) and photosensitizer B comprising an esterification product from tetrahydroxybenzophenone and 1,2-naphthoquinonediazide-5-sulfonic acid having an average esterification rate of Y% (25≦Y≦ (X−10)), with the mixing ratio A:B being 10-90:90-10, is preferred.
    Type: Application
    Filed: June 25, 2002
    Publication date: January 2, 2003
    Inventors: Shuichi Takahashi, Jun Ikemoto, Hidekazu Shioda, Shunji Kawato
  • Patent number: 6492085
    Abstract: The present invention provides a positive photoresist composition including (A) an alkali-soluble resin and (B) a photosensitizer, and the ingredient (B) is a quinonediazide ester of, for example, 2,6-bis[4-hydroxy-3-(2-hydroxy-3,5-dimethylbenzyl)-2,5-dimethylbenzyl]-4-methylphenol, where the average degree of esterification of 20% to 80%.
    Type: Grant
    Filed: August 10, 2000
    Date of Patent: December 10, 2002
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Satoshi Shimatani, Ken Miyagi, Satoshi Niikura, Hidekatsu Kohara, Toshimasa Nakayama
  • Publication number: 20020182531
    Abstract: A positive photoresist composition includes (A) an alkali-soluble novolak resin containing 1,2-naphthoquinonediazidosulfonyl groups substituting for part of hydrogen atoms of phenolic hydroxyl groups, (B) an ester of, for example, a compound represented by the following formula with a naphthoquinonediazidosulfonyl compound, and (C) a sensitizer: 1
    Type: Application
    Filed: April 1, 2002
    Publication date: December 5, 2002
    Applicant: TOKYO OHKA KOGYO CO., LTD.
    Inventors: Jyunichi Mizuta, Kouji Yonemura, Akira Katano, Satoshi Niikura, Kousuke Doi
  • Patent number: 6475694
    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: Grant
    Filed: May 24, 2001
    Date of Patent: November 5, 2002
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Kousuke Doi, Ken Miyagi, Atsuko Hirata, Hidekatsu Kohara, Toshimasa Nakayama
  • Patent number: 6475693
    Abstract: A positive-working radiation-sensitive resin composition showing a good throughput upon production of semiconductors or the like and less process dependence of dimensional accuracy as well as having high sensitivity and high resolution, and being able to form a pattern with good shape and a high aspect ratio.
    Type: Grant
    Filed: August 10, 2000
    Date of Patent: November 5, 2002
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Kenji Susukida, Akio Arano, Masato Nishikawa
  • Publication number: 20020146635
    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,
    Type: Application
    Filed: August 23, 2001
    Publication date: October 10, 2002
    Applicant: Mitsubishi Chemical Corporation
    Inventors: Hideki Nagasaka, Akihisa Murata
  • Patent number: 6461785
    Abstract: A photoresist composition is provided. The photoresist composition includes a polymer resin for forming a photoresist layer, a photosensitive chemical for changing solubility of the photoresist layer when exposed to some form of radiation, and 3-methoxybutyl acetate, 2-heptanone, and 4-butyrolactone as a solvent. The composition has a good photosensitivity and remainder ratio, and no unpleasant odor.
    Type: Grant
    Filed: August 30, 2000
    Date of Patent: October 8, 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: 20020132178
    Abstract: A composition includes (A) an alkali-soluble resin, (B) a quinonediazide ester of a compound represented by the following formula: 1
    Type: Application
    Filed: January 4, 2002
    Publication date: September 19, 2002
    Applicant: TOKYO OHKA KOGYO CO., LTD.
    Inventors: Masaki Kurihara, Takako Suzuki, Kenji Maruyama, Satoshi Niikura, Kousuke Doi
  • Patent number: 6451497
    Abstract: The present invention relates to a positive photosensitive composition, and in particular to a material for plate printing for heat mode printing. The positive photosensitive composition of the present invention comprises at least a diazo compound represented by the following General Formula 1, and a water-insoluble but alkaline water-soluble polymer: (where Z represents an organic group in which the pKa of dissociating H in Ph—NH—Z is 14 or less; and Q1 and Q2 represent organic groups, where Q1 and Q2 may be bonded to form an aliphatic ring or aromatic ring).
    Type: Grant
    Filed: May 16, 2000
    Date of Patent: September 17, 2002
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Kazuto Kunita
  • Patent number: 6451496
    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: Grant
    Filed: February 15, 2001
    Date of Patent: September 17, 2002
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takafumi Ueda, Kenji Araki, Hideto Kato
  • Patent number: 6447975
    Abstract: A photoresist composition including a polymer resin for forming a photoresist layer, a photosensitive chemical that changes the solubility of the photoresist layer when exposed to some form of radiation and 3-methoxybutyl acetate and 4-butyrolactone as a solvent, is provided. The composition has a good photosensitivity and remainder ratio and no unpleasant odor.
    Type: Grant
    Filed: August 30, 2000
    Date of Patent: September 10, 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: 20020119389
    Abstract: The present invention provides a positive photosensitive resin composition which can form a pattern of high resolution and high residual film ratio and has high sensitivity.
    Type: Application
    Filed: January 31, 2002
    Publication date: August 29, 2002
    Inventors: Hiroaki Makabe, Toshio Banba, Takashi Hirano
  • Publication number: 20020119390
    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: February 28, 2002
    Publication date: August 29, 2002
    Applicant: TOKYO OHKA KOGYO CO., LTD.
    Inventors: Takako Suzuki, Sachiko Tamura, Kousuke Doi, Hidekatsu Kohara, Toshimasa Nakayama
  • Patent number: 6440646
    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: Grant
    Filed: February 14, 2001
    Date of Patent: August 27, 2002
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takafumi Ueda, Hideto Kato, Toshihiko Fujii, Miki Kobayashi
  • Patent number: 6440632
    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: Grant
    Filed: August 18, 1999
    Date of Patent: August 27, 2002
    Assignee: Kansai Research Institute
    Inventor: Tokugen Yasuda
  • Patent number: 6436601
    Abstract: An infrared imaging composition comprises a mixture of at least two novolak resins esterified with from about 0.1 to 50 mole % of a 2-diazo-1-naphthol-4 or 5-sulfonic acid or derivative thereof, wherein the degree of esterification of one novolak differs from the degree of esterification of the other by at least about 3 mole %, further mixed with an infrared radiation absorbing compound. When applied to a proper support and processed, the composition is useful as an offset lithographics printing plate, color proofing film or image resist.
    Type: Grant
    Filed: June 25, 2001
    Date of Patent: August 20, 2002
    Assignee: Citiplate, Inc.
    Inventors: Prakash Seth, Charles S. Cusumano
  • Patent number: 6423467
    Abstract: A photosensitive resin composition containing a high molecular compound having at least a) a fluoro aliphatic group, and b) a group represented by formula —L—P (wherein L represents a divalent organic group connected to the skeleton of the high molecular compound, and P represents an aromatic group having a carboxyl group at the ortho-position).
    Type: Grant
    Filed: April 6, 1999
    Date of Patent: July 23, 2002
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Ikuo Kawauchi, Keiji Akiyama, Noriaki Watanabe, Koichi Kawamura
  • Patent number: 6423463
    Abstract: A positive-tone photosensitive resin composition for forming a thick film which is suitably used for photofabrication such as manufacture of circuit boards, a photosensitive resin film, and a method of forming a bump using the same. The photosensitive resin composition comprising (A) a novolac resin with a weight average molecular weight of 2,000-30,000, (B) a polyvinyl lower alkyl ether, (C) a polyphenol derivative compound with a molecular weight of 200-1,000, and (D) a compound containing a naphthoquinonediazido group.
    Type: Grant
    Filed: February 29, 2000
    Date of Patent: July 23, 2002
    Assignee: JSR Corporation
    Inventors: Masaru Oota, Isamu Mochizuki, Kouichi Hirose, Yasuaki Yokoyama, Hozumi Sato
  • Patent number: 6420464
    Abstract: Resin compositions having a low viscosity, a low hygroscopicity, high adhesive properties and a high heat resistance as well as being light in weight and excellent in mechanical properties are provided. The resin compositions include polyhydric phenol compounds represented by the formula (1) and epoxy resins represented by the formula (3).
    Type: Grant
    Filed: April 24, 2000
    Date of Patent: July 16, 2002
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Kenichi Kuboki, Yoshitaka Kajiwara, Eiko Watanabe, Yoshio Shimamura, Katsuhiko Oshimi
  • Publication number: 20020090564
    Abstract: A composition of a positive photosensitive resin precursor includes (a) a polyamic acid ester and/or a polyamic acid each having at least one selected from a carboxyl group, a phenolic hydroxyl group, a sulfonic acid group and a thiol group at the end of a principal chain of the polymer, (b) a compound having a phenolic hydroxyl group, and (c) a quinonediazide sulfnate. The composition can be subjected to dissolution in an alkaline developer.
    Type: Application
    Filed: November 1, 2001
    Publication date: July 11, 2002
    Inventors: Mitsuhito Suwa, Kazuto Miyoshi, Masao Tomikawa
  • Patent number: 6417317
    Abstract: A novolak resin precursor is composed of bonded phenolic moieties, one of the hydrogen atoms in the o- or p-positions relative to the hydroxy group of each phenolic moiety is substituted with an alkyl or alkenyl group having 1 to 3 carbon atoms, and the other two hydrogen atoms are bonded through methylene bonds. The content of ortho-ortho bonding is 30 to 70% relative to the number of total methylene bonds and the weight average molecular weight of the precursor is 300 to 10,000. A novolak resin is obtained from this precursor, and a positive photoresist composition comprises this novolak resin. The invention provides a positive photoresist composition that comprises less binuclear compounds, suppresses scum formation, is excellent in terms of definition and coating performance and provides a resist pattern having satisfactory heat resistance.
    Type: Grant
    Filed: December 13, 1999
    Date of Patent: July 9, 2002
    Assignee: Togyo Ohka Kogyo Co., Ltd.
    Inventors: Ken Miyagi, Kousuke Doi, Ryuusaku Takahashi, Hidekatsu Kohara, Toshimasa Nakayama
  • Publication number: 20020081517
    Abstract: A lithographic printing plate has a coating which is imaged by heating an area of the coating with an infrared laser and actinically reacting the coating in the heated area with ultraviolet or visible radiation. The coating can be either positive working or negative working and the coating contains an infrared absorber. The imaging time is reduced since the actinic reaction rate is increased at the elevated temperature.
    Type: Application
    Filed: December 22, 2000
    Publication date: June 27, 2002
    Applicant: Howard A. Fromson
    Inventors: Howard A. Fromson, William J. Rozell
  • Patent number: 6410207
    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: January 10, 2000
    Date of Patent: June 25, 2002
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Hideki Nagasaka, Akihisa Murata
  • 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