Quinone Diazide Containing Layer Patents (Class 430/165)
  • 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: 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
  • 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: 20010028990
    Abstract: A lithographic printing plate having an average curvature in a rolling direction of 1.5×10−3 mm−1 or less, a curvature distribution in a crosswise direction of 1.5×10−3 mm−1 or less, and a curvature in a direction perpendicular to said rolling direction of 1.0×10−3 mm−1 or less and a method for producing the printing plate are disclosed. A method for producing a support for a lithographic printing plate is also disclosed, which comprises roughening a surface of an aluminum web having a center line average surface roughness of 0.15 to 0.35 &mgr;m and a maximum surface roughness of 1 to 3.5 &mgr;m by at least one of mechanical surface roughening, chemical etching and electrochemical surface roughening, and then applying anodization thereto.
    Type: Application
    Filed: March 23, 2001
    Publication date: October 11, 2001
    Inventors: Akio Uesugi, Masahiro Endo
  • 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
  • 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
  • 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
  • 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: 6232037
    Abstract: A lithographic printing plate having an average curvature in a rolling direction of 1.5×10−3 mm−1 or less, a curvature distribution in a crosswise direction of 1.5×10−3 mm−1 or less, and a curvature in a direction perpendicular to said rolling direction of 1.0×10−3 mm−1 or less and a method for producing the printing plate are disclosed. A method for producing a support for a lithographic printing plate is also disclosed, which comprises roughening a surface of an aluminum web having a center line average surface roughness of 0.15 to 0.35 &mgr;m and a maximum surface roughness of 1 to 3.5 &mgr;m by at least one of mechanical surface roughening, chemical etching and electrochemical surface roughening, and then applying anodization thereto.
    Type: Grant
    Filed: October 10, 1997
    Date of Patent: May 15, 2001
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Akio Uesugi, Masahiro Endo, Hirokazu Sakaki
  • 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: 6207340
    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 the 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: March 27, 2001
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Masaki Kurihara, Satoshi Niikura, Miki Kobayashi, Kousuke Doi, Hidekatsu Kohara, Toshimasa Nakayama
  • Patent number: 6197473
    Abstract: The objectives of the present invention are to provide a photosensitive composition having high solubility to organic solvents as well as to alkaline developers or water-base developers of pH 11 or less, and to provide a pattern forming process for obtaining a high-resolution resist pattern. These objectives are achieved by means of a photosensitive composition comprising a compound which is glassy at room temperature and has a cyclic structure with three or more aromatic rings containing an acid-decomposable substituent, and a pattern forming process wherein a photosensitive material using said photosensitive composition is exposed to a light pattern and developed with an aqueous solution of an alkali or with a water-base developer of pH 11 or less.
    Type: Grant
    Filed: September 17, 1998
    Date of Patent: March 6, 2001
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Naoko Kihara, Satoshi Saito, Toru Ushirogouchi
  • Patent number: 6190825
    Abstract: The invention relates to polymers containing N-substituted maleimide units, to a positive- or negative-working radiation-sensitive mixture comprising a) a polymeric binder which is insoluble in water, but soluble in aqueous-alkaline solutions, and b) at least one radiation-sensitive compound, where the binder comprises a polymer containing N-substituted maleimide units of the formula (I) The invention furthermore relates to a recording material having a support and a radiation-sensitive layer, where the layer includes the mixture. The recording material is particularly suitable for the production of chemical-resistant relief recordings. The planographic printing plates produced from the recording material allow long print runs and are resistant to processing chemicals.
    Type: Grant
    Filed: January 29, 1999
    Date of Patent: February 20, 2001
    Assignee: Agfa-Gevaert N.V.
    Inventors: Steffen Denzinger, Andreas Elsaesser
  • Patent number: 6177226
    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 the 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: April 29, 1998
    Date of Patent: January 23, 2001
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Masaki Kurihara, Satoshi Niikura, Miki Kobayashi, Kousuke Doi, Hidekatsu Kohara, Toshimasa Nakayama
  • Patent number: 6171750
    Abstract: A radiation-sensitive resin composition including (A) an alkali-soluble novolak resin obtained by condensing a particular combination of a first phenol having formula: wherein R1 and R2 are the same or different and each represent an alkyl group, a cycloalkyl group, an alkoxyl group or an aryl group; and a second phenol selected from the group consisting of phenol, o-cresol, m-cresol, p-cresol, 2,3-dimethylphenol, 2,5-dimethylphenol, 2,6-dimethylphenol, 3,4-dimethylphenol, 3,5-dimethylphenol, 2,3,5-trimethylphenol, 3,4,5-trimethylphenol, resorcinol, 2-methylresorcinol, 4-ethylresorcinol, hydroquinone, methylhydroquinone, catechol, 4-methyl-catechol, pyrogallol, phloroglucinol, thymol and isothymol with an aldehyde in the presence of an acidic catalyst; and (B) a quinonediazidosulfonic acid ester compound. This composition exhibits good resolution, developability, heat resistance, pattern shape, exposure margin and focal latitude in a well balanced state.
    Type: Grant
    Filed: June 10, 1998
    Date of Patent: January 9, 2001
    Assignee: JSR Corporation
    Inventors: Katsumi Inomata, Katsuji Douki, Tooru Mizumachi, Shin-ichiro Iwanaga
  • Patent number: 6156474
    Abstract: To provide a positive type photoresist composition which is capable of forming a resist pattern having an excellent adhesion to a substrate, a positive type photoresist composition comprising a polymer containing a specified amount of a polypropylene oxide group and a polyethylene oxide group is provided.
    Type: Grant
    Filed: December 2, 1998
    Date of Patent: December 5, 2000
    Assignee: Shipley Company, L.L.C.
    Inventors: Sigeki Nakano, Akira Awaji, Teruaki Ogawa, Kenta Takahashi
  • Patent number: 6140026
    Abstract: A photosensitive compound comprising at least one o-quinonediazide sulfonic acid ester of a phenolic compound, said esters selected from the group consisting of formula (II): ##STR1## wherein the photosensitive compound is used in a radiation sensitive composition and a process for forming a positive patterned image.
    Type: Grant
    Filed: December 8, 1999
    Date of Patent: October 31, 2000
    Assignee: Arch Specialty Chemicals, Inc.
    Inventors: Andrew J. Blakeney, Arturo N. Medina, Medhat A. Toukhy, Lawrence Ferreira, Alfred T. Jeffries, III, Ahmad A. Naiini
  • Patent number: 6127087
    Abstract: A positive photoresist composition comprises (A) an alkali-soluble resin, and (B) at least one quinonediazide group-containing compound in which part or all of the hydroxyl groups of a compound represented by the following formula (I) are esterified with a quinonediazidesulfonic acid: ##STR1## wherein each of R.sup.1 and R.sup.2 is an alkyl group having 1 to 5 carbon atoms, and "a" is 0 or 1. The present invention provides a positive photoresist composition which can form a resist pattern having high film residual rate, improved development contrast between exposed portions and unexposed portions, and satisfactory definition, exposure margin, focal depth range properties and sectional shape.
    Type: Grant
    Filed: June 17, 1998
    Date of Patent: October 3, 2000
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Miki Kobayashi, Kousuke Doi, Sachiko Tamura, Hidekatsu Kohara, Toshimasa Nakayama
  • Patent number: 6117610
    Abstract: An infrared imaging composition contains two essential components, a non-basic infrared radiation absorbing material (such as carbon black), and a phenolic resin that is either mixed or reacted with an o-diazonaphthoquinone derivative. These compositions are useful in positive-working or negative-working imaging elements such as lithographic printing plates that can be adapted to direct-to-plate imaging procedures.
    Type: Grant
    Filed: August 8, 1997
    Date of Patent: September 12, 2000
    Assignee: Kodak Polychrome Graphics LLC
    Inventors: Eugene L. Sheriff, Paul R. West, Jeffery A. Gurney, Thap DoMinh
  • Patent number: 6083657
    Abstract: Phenolic compound (a) is polycondensed with mixed aldehyde (b) consisting essentially of 5-30 mol % of unsaturated aliphatic aldehyde (b-1) and 70-95 mol % of saturated aliphatic aldehyde (b-2) to give alkali-soluble novolak resin (A) as the product of polycondensation reaction. The alkali-soluble novolak resin (A) is used with quinonediazido group containing compound (B) to produce a positive photoresist composition. According to the present invention, there are specifically provided a positive photoresist composition that has high feature integrity in spite of high sensitivity and which yet provides a great depth of focus, a process for producing such positive photoresist composition, as well as an alkali-soluble novolak resin that can advantageously be used in such composition, and a method of forming patterns with high reproducibility using such positive photoresist composition.
    Type: Grant
    Filed: January 15, 1999
    Date of Patent: July 4, 2000
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Shinichi Kono, Yasuo Masuda, Atsushi Sawano, Hayato Ohno, Hidekatsu Kohara, Toshimasa Nakayama
  • Patent number: 6080522
    Abstract: A radiation sensitive resist composition with high sensitivity, capable of forming a highly heat-resistant resist pattern. The radiation-sensitive resist composition contains, together with a resist material, a polymer which is obtained by reacting (a) a xylylene compound, (b) salicylic acid and (c) 9,9'-bis(hydroxyphenyl)fluorene derivatives or diol compounds of 3,3,3',3'-tetramethyl-2,3,2',3'-tetrahydro-(1,1')-spirobiindene, and which has a weight average molecular weight of 1,000 to 5,000 and Tg of 100 to 150.degree. C. Examples of (c) include 9,9'-bis(4-hydroxyphenyl)fluorene and 3,3,3',3'-tetramethyl-2,3,2',3'-tetrahydro-(1,1')-spirobiindene-6,6'-diol. As the resist material, any of positive- and negative-working resists may be used, with that comprising an alkali-soluble resin and a quinonediazide photo-sensitizer being preferably used.
    Type: Grant
    Filed: February 26, 1999
    Date of Patent: June 27, 2000
    Assignee: Clariant Internaitonal, Ltd.
    Inventors: Hiromi Ito, Hatsuyuki Tanaka
  • Patent number: 6071666
    Abstract: A positive type photosensitive resin composition which comprises (A) 100 parts by weight of a polyamide represented by the general formula (1): ##STR1## wherein X represents a tetravalent aromatic group; Y represents a divalent aromatic group; Z represents a group represented by the formula: ##STR2## in which R.sub.1 and R.sub.2 represent organic groups and R.sub.3 and R.sub.4 represent monovalent organic groups; a and b represent molar fractions; a+b=100 mole %; a=60.0-100.0 mole %; b=0-40.0 mole %; and n represents an integer of 2 to 500, (B) 1 to 100 parts by weight of a photosensitive diazoquinone compound and (C) 1 to 50 parts by weight of a phenol compound represented by a specific structural formula and/or (D) 0.1 to 20 parts by weight of an organosilicon compound represented by a specific structural formula; and a semiconductor device in which a pattern of a polybenzoxazole resin obtained by using the above photosensitive resin composition is formed in a thickness of 0.1 to 20 .mu.
    Type: Grant
    Filed: May 12, 1997
    Date of Patent: June 6, 2000
    Assignee: Sumitomo Bakelite Company, Ltd.
    Inventors: Takashi Hirano, Toshio Banba, Hiroaki Makabe, Naoshige Takeda, Toshiro Takeda
  • Patent number: 6068962
    Abstract: A non-chemically enhanced type positive resist composition includes an alkali-soluble novolak resin, a quinonediazide type sensitizer and at least one of the following compounds (a) and (b):(a) an acid-generator which is decomposed by the action of an alkali developer and generates an acid, and(b) compounds represented by the following formula (IV) or (V): ##STR1## wherein each of R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7 and R.sup.8 independently represents hydrogen, halogen, hydroxy, alkyl, alkoxy, aryl or nitro, each of R.sup.9 and R.sup.10 independently represents hydrogen, halogen, alkyl, aryl, nitro, a group of --(CH.sub.2).sub.n --OR.sup.11 or a group of --(CH.sub.2).sub.n --COOR.sup.12 in which R.sup.11 represents hydrogen, alkyl, aryl or alkanoyl and R.sup.12 represents hydrogen, alkyl or aryl, and n is a number from 0 to 3 and R.sup.13 represents hydrogen, halogen, alkyl, alkoxy or aryl.
    Type: Grant
    Filed: September 19, 1997
    Date of Patent: May 30, 2000
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yasunori Uetani, Hiroshi Moriuma, Jun Tomioka
  • Patent number: 6066438
    Abstract: A method for fixing, on a substrate, functional material such as proteins, enzymes, polysaccharides, nucleic acids, microorganisms, viruses and cultured cells, includes the steps of (i) forming on the substrate a photosensitive layer containing DNQ, novolak, and optionally imidazole; (ii) applying onto the substrate functional material containing at least one amino group; (iii) before or after step (ii), irradiating in a pattern the photosensitive layer with light of appropriate wavelength(s) to convert DNQ to a ketene compound; and (iv) reacting the amino group with the ketene compound to fix via amido bonding the functional material to the substrate via the photosensitive layer along the pattern.
    Type: Grant
    Filed: March 10, 1997
    Date of Patent: May 23, 2000
    Assignee: Director General of Industrial Science & Technology
    Inventors: Dan V. Nicolau, Takahisa Taguchi, Susumu Yoshikawa
  • Patent number: 6060217
    Abstract: A method for directly imaging a lithographic printing surface using infrared radiation without the requirement of pre- or post-UV-light exposure, or heat treatment employs a printing plate which contains a support with a hydrophilic surface overcoated with an imaging layer. The imaging layer contains at least one polymer having bonded pendent groups which are hydroxy, carboxylic acid, tert-butyl-oxycarbonyl, sulfonamide, amide, nitrile, urea, or combinations thereof; as well as an infrared absorbing compound. The imaging layer may contain a second polymer which has bonded pendent groups which are 1,2-napthoquinone diazide, hydroxy, carboxylic acid, sulfonamide, hydroxymethyl amide, alkoxymethyl amide, nitrile, maleimide, urea, or combinations thereof. The imaging layer may also contain a visible absorption dye, a solubility inhibiting agent, or both.
    Type: Grant
    Filed: September 2, 1997
    Date of Patent: May 9, 2000
    Assignee: Kodak Polychrome Graphics LLC
    Inventors: My T. Nguyen, Nishith Merchant, Ken-Ichi Shimazu, S. Peter Pappas, Robert Hallman, Jerome Philip Kesselman, Celin Savariar-Hauck, Gerhard Hauck, Hans-Joachim Timpe, Omkar J. Natu, Ajay Shah
  • Patent number: 6048659
    Abstract: A radiation-sensitive resin composition including (1) an alkali-soluble resin, (2) a quinonediazide compound and (3) a mixed solvent including a monoketone having 7 to 14 carbon atoms and an alkoxypropionic acid alkyl ester is provided. The composition can be coated in a uniform thickness in a small coating weight. The composition has a high sensitivity and a high resolution, and also enables formation of resist patterns having a superior pattern shape with less pattern defects. Thus, it is suitable as a positive resist.
    Type: Grant
    Filed: October 2, 1998
    Date of Patent: April 11, 2000
    Assignee: JSR Corporation
    Inventors: Masaaki Inoue, Katsumi Inomata, Hiromichi Hara, Yoshiji Yumoto
  • Patent number: 6048665
    Abstract: The present invention provides for process of preparing a photoactive ester compound of high purity using a solid base catalyst, preferably an anionic exchange resin. The invention further provides for preparing and imaging a photosensitive composition comprising such a photoactive compound, a film-forming resin and a solvent composition.
    Type: Grant
    Filed: May 27, 1999
    Date of Patent: April 11, 2000
    Assignee: Clariant Finance (BVI) Limited
    Inventor: Joseph E. Oberlander
  • Patent number: 6045963
    Abstract: A negative waterless plate contains a sheet substrate; a radiation sensitive imaging layer composed of a diazido naphthaquinone ester or amide compound, such as diazido naphthaquinone sulfonate of a phenolic resin, and a polyurethane prepared by reacting a di-isocyanate and a diol; and a silicone layer. The planographic printing plate is imagewise exposed to actinic radiation through a negative original to form exposed areas of the imaged layer which are soluble or dispersible in a developer liquid. After imaging exposure, the developer liquid is applied which penetrates the silicone layer and dissolves the areas exposed to the radiation. The coating areas not exposed by the radiation remain intact. During this development procedure, areas of the silicone layer overlying the exposed areas are removed along with the underlying soluble areas to produce an imaged planographic printing plate having uncovered ink receptive areas and complimentary ink repellent areas of the silicone layer.
    Type: Grant
    Filed: March 17, 1998
    Date of Patent: April 4, 2000
    Assignee: Kodak Polychrome Graphics LLC
    Inventors: Jianbing Huang, Richard Goodman, Thi Do
  • Patent number: 6040107
    Abstract: A photosensitive compound comprising at least one o-quinonediazide sulfonic acid ester of a phenolic compound, said esters selected from the group consisting of formula (II): ##STR1## wherein the photosensitive compound is used in a radiation sensitive composition and a process for forming a positive patterned image.
    Type: Grant
    Filed: February 6, 1998
    Date of Patent: March 21, 2000
    Assignee: Olin Microelectronic Chemicals, Inc.
    Inventors: Andrew J. Blakeney, Arturo N. Medina, Medhat A. Toukhy, Lawrence Ferreira, Alfred T. Jeffries, III, Ahmad A. Naiini
  • Patent number: 6013407
    Abstract: A positive resist composition is excellent in sensitivity, film loss after development, resolution, thermal-flow resistance, storage stability, exposure margin and focus margin and comprises in combination (A) an alkali-soluble phenol resin, (B) a quinonediazide sulfonate type photosensitive agent and (C) a phenolic compound, wherein the phenolic compound (C) is at least one phenolic compound selected from the group consisting of phenolic compounds (CX) having a structural unit represented by the following formula (I) and phenolic compounds (CD) having a structural unit represented by the following formula (II): ##STR1## wherein R.sup.1 to R.sup.3 are, independently of one another, a hydrogen atom, a hydroxyl group, a halogen atom, an alkyl group which may be substituted, a cycloalkyl group which may be substituted, an alkenyl group which may be substituted, an alkoxy group which may be substituted, or an aryl group which may be substituted, R.sup.4 to R.sup.
    Type: Grant
    Filed: July 8, 1997
    Date of Patent: January 11, 2000
    Assignee: Nippon Zeon Co., Ltd.
    Inventors: Shoji Kawata, Hiroshi Hayashi, Hirokazu Higashi, Takeyoshi Kato, Masahiro Nakamura
  • Patent number: 6010816
    Abstract: Disclosed is an aluminum alloy support for a planographic printing plate, wherein the sodium content of the support is 0.005 to 0.040 weight %.
    Type: Grant
    Filed: December 30, 1997
    Date of Patent: January 4, 2000
    Assignee: Konica Corporation
    Inventors: Kazuyuki Nishio, Takahiro Mori
  • Patent number: 6007961
    Abstract: A radiation-sensitive resin composition including an alkali soluble resin and a quinonediazide compound is provided. The quinonediazide compound has the formula (1), for example: ##STR1## wherein, R.sup.1 to R.sup.6 are an alkyl, cycloalkyl or aryl group; a and b are an integer of 1 to 3; D.sup.1 and D.sup.2 are independently a hydrogen atom or a 1,2-quinonediazidosulfonyl group, provided that at least one of D.sup.1 is a 1,2-quinonediazidosulfonyl group; A is a bonding such as single bond; and x and y are an integer of 0 to 2. The composition is suitable as a positive resist, which effectively restrains the occurrence of scum, and excellent in developability, pattern shape, sensitivity, resolution and focus latitude.
    Type: Grant
    Filed: December 10, 1997
    Date of Patent: December 28, 1999
    Assignee: JSR Corporation
    Inventors: Katsumi Inomata, Masahiro Akiyama, Shin-ichiro Iwanaga, Akira Tsuji
  • Patent number: 6001517
    Abstract: A positive photosensitive polymer composition, which comprises a thermosetting polymer precursor which can be cured through cyclodehydration upon heating, and a photosensitive cure accelerator which can be inactivated of its cure accelerating property by irradiation of light.
    Type: Grant
    Filed: October 29, 1997
    Date of Patent: December 14, 1999
    Assignee: Kabushiki Kaisha Toshiba
    Inventor: Yoshiaki Kawamonzen
  • Patent number: 5998084
    Abstract: A positive-working, radiation-sensitive recording material capable of being used for the production of planographic printing plates, comprising: an aluminum support and a radiation-sensitive layer coated thereon, whereinthe aluminum support has been grained in nitric acid, then cleaned in sulfuric acid, anodized in sulfuric acid, and subsequently hydrophilized with a compound comprising at least one unit with a phosphonic acid or phosphonate group; andthe radiation-sensitive layer comprisesa) a radiation-sensitive 1,2-naphthoquinone-2-diazide-4- or -5-sulfonic acid ester of a polycondensate having phenolic hydroxy groups, said polycondensate being obtained by reacting a phenolic compound with an aldehyde or ketone,b) a novolak or a polycondensation product obtained by reacting a polyphenol with an aldehyde or ketone, as an alkali-soluble resin,c) a vinyl-type polymer comprising at least one unit having a lateral hydroxyphenyl group,d) a clathrate-forming compound,e) a low-molecular weight compound which compr
    Type: Grant
    Filed: November 15, 1996
    Date of Patent: December 7, 1999
    Assignee: Agfa-Gevaert N.V.
    Inventors: Andreas Elsaesser, Raimund Haas, Guenter Hultzsch, Peter Lehmann, Rudolf Neubauer, Rudolf Zertani
  • Patent number: 5994031
    Abstract: Disclosed is a method of processing an exposed presensitized planographic printing plate employing an automatic processor, the method comprising the steps of developing the exposed presensitized planographic printing plate with a developer; and washing the developed printing plate with a washing water, wherein the ratio W/D of the washing time W to the cross-over time D taken from completion of the developing step to the beginning of the washing step is 3 or more.
    Type: Grant
    Filed: September 4, 1997
    Date of Patent: November 30, 1999
    Assignee: Konica Corporation
    Inventors: Yoko Hirai, Yasuhisa Sugi
  • Patent number: 5981135
    Abstract: A positive acting photoresist composition (e.g., a monolayer dry film) which is strippable in aqueous alkaline solution comprises a photo acid generator and a UV-transparent resin binder system which allows efficient photo bleaching of the photoactive component. An acid functional cellulosic resin may be the only binder resin, an acidic acrylate resin being optional. The dry coating is flexible and may be used as an etch and plating resist.
    Type: Grant
    Filed: August 13, 1997
    Date of Patent: November 9, 1999
    Assignee: Morton International, Inc.
    Inventors: Thomas A. Koes, Grieg B. Beltramo
  • Patent number: 5958645
    Abstract: A radiation-sensitive resin composition comprising:(i) an alkali-soluble resin;(ii) a phenol compound represented by the following formula (1): ##STR1## wherein R.sub.1 to R.sub.4 each represent halogen, alkyl, alkoxyl, aryl, nitro, cyano, hydroxyalkyl, hydroxyalkoxyl or hydroxyl; a, b, c and d each represent an integer of 0 to 4 and satisfying 0.ltoreq.a+b.ltoreq.4 and 0.ltoreq.c+d.ltoreq.4, provided that when a+b is 1 and c+d is 1 at least one of R.sub.1 (or R.sub.2) and R.sub.3 (or R.sub.4) is alkyl, hydroxyalkyl or hydroxyalkoxyl; R.sub.5 to R.sub.10 each represent hydrogen, alkyl or aryl; and X.sub.1 and X.sub.2 each represent oxygen or sulfur atom; and(iii) a 1,2-quinonediazide compound. This composition has good resolution, sensitivity and developability, as well as has as a positive resist good focal latitude and heat resistance. The patterns formed have good shapes, and the composition may cause no fine particles during storage.
    Type: Grant
    Filed: August 27, 1997
    Date of Patent: September 28, 1999
    Assignee: Japan Synthetic Rubber Co., Ltd.
    Inventors: Kouichi Hirose, Masahiro Akiyama, Katsumi Inomata, Yoshiji Yumoto
  • Patent number: 5948587
    Abstract: Provided is a positive working photoresist composition comprising (A) an alkali-soluble novolak resin obtained by condensation reaction of a mixture of phenols, which are constituted of specified proportions of m-cresol and two kinds of specific phenols, with an aldehyde and having a Mw/Mn ratio of from 1.5 to 4.0 (wherein Mw stands for a weight-average molecular weight, and Mn stands for a number-average molecular weight); (B) a 1,2-naphthoquinonediazide-5-(and/or -4-)sulfonic acid ester as a photosensitive material; and (C) a low molecular weight compound having from 12 to 50 carbon atoms per molecule and from 2 to 8 phenolic hydroxy groups per molecule.
    Type: Grant
    Filed: September 19, 1996
    Date of Patent: September 7, 1999
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Yasumasa Kawabe, Shiro Tan
  • Patent number: 5942369
    Abstract: A positive photoresist composition including (A) 100 parts by weight of an alkali-soluble novolak resin, and based thereon; (B) 5 to 50 parts by weight of an alkali-soluble acrylic resin containing, as s, 10 to 80% by weight of a unit of a radical-polymerizable compound having an alcoholic hydroxyl group and 3 to 50% by weight of at least one of a unit of a radical-polymerizable compound having a carboxyl group and a unit of a radical-polymerizable compound having a phenolic hydroxyl group; (C) 5 to 100 parts by weight of a quinonediazide group-containing compound; and (D) a solvent, is provided. This composition has a good adhesion to substrates at the time of development and a good plating solution resistance and moreover can be well wetted with plating solutions, can be well developed with alkali developing solutions and can be well stripped from substrates at the resist unexposed areas, and is suited for the formation of thick films suitable as bump forming materials.
    Type: Grant
    Filed: January 27, 1998
    Date of Patent: August 24, 1999
    Assignee: JSR Corporation
    Inventors: Toshiyuki Ota, Kimiyasu Sano, Masaru Ohta, Hozumi Sato
  • Patent number: 5912102
    Abstract: A positive resist composition comprising an alkali-soluble phenolic resin, a photosensitive agent composed of a quinonediazide sulfonate of a specific polyhydroxy compound, and an aromatic compound having at least one phenolic hydroxyl group.
    Type: Grant
    Filed: June 26, 1997
    Date of Patent: June 15, 1999
    Assignee: Nippon Zeon Co., Ltd.
    Inventors: Shoji Kawata, Motofumi Kashiwagi, Teturyo Kusunoki, Masahiro Nakamura
  • Patent number: 5876895
    Abstract: A photosenstive resin composition for color filter having excellent resolution, heat resistance and transparency, etc., characterized in that it contains a novolak resin having the recurring units such as those represented by the general formula (I): ##STR1## ?wherein R.sub.1 to R.sub.5 represent hydrogen, alkyl, etc., and R.sub.6 and R.sub.7 represent hydrogen, alkyl, etc., provided that ##STR2## is coordinated at the o- or p-position in relation to the --OH group! and having a molecular weight of about 1,000-50,000, a solvent and a dye or pigment.
    Type: Grant
    Filed: May 24, 1996
    Date of Patent: March 2, 1999
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yoshiki Hishiro, Naoki Takeyama, Shigeki Yamamoto
  • Patent number: 5861229
    Abstract: A positive resist composition which comprises a 1,2-quinone diazide compound and an alkali-soluble resin containing a polyphenol compound (I) of the general formula:X--.alpha.--H (I)wherein x is a group of the formula: ##STR1## and .alpha. is a divalent group which comprises a repeating unit of the formula: ##STR2## in which n is a number of not less than 1; a, b, c, d, e and f are the same or different and a number of 0-3, provided that d+f is not less than 1; R.sub.1, R.sub.2 and R.sub.3 are the same or different and a C.sub.1 -C.sub.18 alkyl group, a C.sub.1 -C.sub.18 alkoxy group, a carboxyl group or a halogen atom; R.sub.4 is a hydrogen atom, a C.sub.1 -C.sub.18 alkyl group or an aryl group, which resist composition is sensitive to radiation and has good balance of sensitivity, resolving power and heat resistance.
    Type: Grant
    Filed: September 22, 1992
    Date of Patent: January 19, 1999
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Haruyoshi Osaki, Fumio Oi, Yasunori Uetani, Makoto Hanabata, Takeshi Hioki
  • Patent number: 5858605
    Abstract: A photoresist composition comprising an alkali soluble resin and the reaction product of an ortho-naphthoquinone diazide sulfonic acid ester and a vinyl ether. In use, the photoresist is characterized by having at least a portion of the hydroxyl groups on the alkali soluble resin reacted with the photoactive compound and then deblocked by acid generation.
    Type: Grant
    Filed: March 8, 1997
    Date of Patent: January 12, 1999
    Assignee: Shipley Company, L.L.C.
    Inventors: Roger F. Sinta, Daniel Y. Pai
  • 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