Polymeric Quinone Diazide Patents (Class 430/190)
  • Patent number: 6790581
    Abstract: A phenolic resin/silicone resin hybrid compound is obtained by effecting hydrolytic condensation of an organooxysilane in the co-presence of a phenolic resin. The hybrid compound is used as the base polymer in a resist for endowing a resist film with excellent adhesion to a metal substrate.
    Type: Grant
    Filed: October 11, 2002
    Date of Patent: September 14, 2004
    Assignee: Shin-Etsu Chemical Company, Limited
    Inventors: Hideto Kato, Tomoyoshi Furihata
  • Patent number: 6790582
    Abstract: The present invention relates to a composition and a process for preparing a composition that comprises: a) a novolak resin partially esterified with from about 3 to about 7 weight percent of a naphthoquinonediazidosulfonyl group; b) one or more dilution resins; and c) at least one solvent.
    Type: Grant
    Filed: April 1, 2003
    Date of Patent: September 14, 2004
    Assignee: Clariant Finance BVI Limited
    Inventor: J. Neville Eilbeck
  • Patent number: 6783914
    Abstract: The present invention describes encapsulated inorganic resists which are compatible with conventional resist processing such as spin casting from organic solvents and development with aqueous 2.38% TMAH developers. The resist includes encapsulated inorganic materials as resist components, a fact that significantly increases the plasma etch selectivity of the resists compared to conventional polymeric resists. In effect, these resist systems act as a photoimagable single layer hard mask, although use as the top layer in a bilayer resist scheme is contemplated.
    Type: Grant
    Filed: February 25, 2000
    Date of Patent: August 31, 2004
    Assignee: Massachusetts Institute of Technology
    Inventor: Theodore H. Fedynyshyn
  • Patent number: 6773858
    Abstract: A photoresist composition comprising a novolac resin in which 3-27 mol % of the hydroxyl group hydrogens are substituted with 1,2-naphthoquinonediazidosulfonyl groups and an alkali-soluble cellulose whose glucose ring substituent groups are substituted with organic groups at a specific rate is used in microprocessing as a positive photoresist and offers many advantages including uniformity, high sensitivity, high resolution, good pattern shape, heat resistance, film retention, substrate adhesion, shelf stability, and high throughput.
    Type: Grant
    Filed: August 6, 2003
    Date of Patent: August 10, 2004
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Hideto Kato, Kyoko Soga, Tomoyoshi Furihata
  • Publication number: 20040131964
    Abstract: A positive resist composition contains a novolak resin in which 3-27 mol % of the hydroxyl group hydrogens are substituted with 1,2-naphthoquinonediazidosulfonyl ester groups, a methyl vinyl ether-monoalkyl maleate copolymer and optionally, an alkali-soluble cellulose whose glucose ring substituent groups are substituted with organic groups at a specific rate. The composition is useful as a thick film photoresist which is subject to a plating step and offers many advantages including high sensitivity, perpendicular geometry, high resolution, and crack resistance during and after the plating step.
    Type: Application
    Filed: December 18, 2003
    Publication date: July 8, 2004
    Inventors: Tomoyoshi Furihata, Hideto Kato
  • Publication number: 20040110090
    Abstract: Processes for imaging and developing imageable elements useful as lithographic printing plate precursors either thermally or with ultraviolet radiation that use the same developer are disclosed. The imageable elements comprise a top layer and an underlayer. The top layer contains a phenolic polymer and a material that has either the o-benzoquinonediazide functionality or the o-diazonaphthoquinone functionality. The developer is a 20:80 to 80:20 mixture of (1) an aqueous alkaline developer that has a pH greater than 11 and contains about 2 wt % to about 8 wt % of an alkali metal silicate, and (2) a solvent based developer that contains about 0.5 wt % to about 15 wt % of an organic solvent or mixture of organic solvents.
    Type: Application
    Filed: December 4, 2002
    Publication date: June 10, 2004
    Inventors: Jayanti Patel, Kevin B. Ray, Jianbing Huang
  • Patent number: 6746812
    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: May 23, 2001
    Date of Patent: June 8, 2004
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Noriaki Watanabe, Koichi Kawamura, Kazuo Fujita, Takeshi Serikawa, Akira Nagashima
  • Patent number: 6730769
    Abstract: (i) As a primary reaction, m-cresol is allowed to react with propionaldehyde in the presence of an acid catalyst and thereby yields a polymer having a weight average molecular weight Mw of 200 to 500 and a molecular weight distribution Mw/Mn of 1.7 or less, and (ii) as a secondary reaction, the polymer is allowed to react with 3,4-xylenol and formaldehyde and thereby yields a novolak resin having an Mw of 1000 to 20000. By adding a specific photosensitizer, the novolak resin yields a positive photoresist composition.
    Type: Grant
    Filed: May 1, 2002
    Date of Patent: May 4, 2004
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Akira Katano, Mitsuo Hagihara, Ken Miyagi, Toshiaki Tachi
  • Publication number: 20040076911
    Abstract: The invention is a photoswitchable benzocyclobutene-based polymer that while remaining aqueous developable, avoids the problem of significant moisture uptake. The oligomer or polymer comprises a polymeric backbone, benzocyclobutene reactive groups, and photoswitchable pendant groups. The pendant groups are bonded to the polymeric backbone and are characterized by the presence of a moiety that converts to carboxylic acid upon exposure to activating wavelengths of radiation a carboxylic acid. When the oligomer or polymer is subsequently heated to cause cure of the oligomer or polymer, carbon dioxide is emitted and the group forms a substantially non-polar moiety. The invention is also a method of making such a polymer and a method of forming a patterned film using such a polymer.
    Type: Application
    Filed: October 18, 2002
    Publication date: April 22, 2004
    Inventors: Ying Hung So, Keith J. Watson, Scott J. Bis
  • Patent number: 6706454
    Abstract: A coating solution useful in the preparation of printing plate precursors comprises: a) a radiation sensitive composition C comprising a phenolic resin; b) at least one thermoplastic polymer P which has a solubility in aqueous alkaline media ranging from sparingly soluble to insoluble; c) a first solvent component A which is capable of solubilizing both composition C and thermoplastic polymer P; d) a second solvent component B having a volatility less than component A, wherein component B is capable of volatilizing composition C but not thermoplastic polymer P, and composition C and thermoplastic P are homogeneously dissolved in a mixture of components A and B; and e) at least one further polymer AP having a higher molecular weight than the phenolic resin of composition C, wherein polymer AB is miscible with the phenolic resin and immiscible with thermoplastic polymer P.
    Type: Grant
    Filed: July 5, 2001
    Date of Patent: March 16, 2004
    Assignee: Kodak Polychrome Graphics LLC
    Inventor: Mathias Jarek
  • Publication number: 20040029032
    Abstract: A photoresist composition comprising a novolac resin in which 3-27 mol % of the hydroxyl group hydrogens are substituted with 1,2-naphthoquinonediazidosulfonyl groups and an alkali-soluble cellulose whose glucose ring substituent groups are substituted with organic groups at a specific rate is used in microprocessing as a positive photoresist and offers many advantages including uniformity, high sensitivity, high resolution, good pattern shape, heat resistance, film retention, substrate adhesion, shelf stability, and high throughput.
    Type: Application
    Filed: August 6, 2003
    Publication date: February 12, 2004
    Inventors: Hideto Kato, Kyoko Soga, Tomoyoshi Furihata
  • Publication number: 20040023166
    Abstract: The present invention provides methods of forming and using thermally imageable composite elements which may be developed into lithographic printing plates. More specifically, the present invention provides a method of forming thermally imageable composite elements which provide substantial developer resistance in desired regions, while maintaining white light desensitivity and durability.
    Type: Application
    Filed: July 30, 2002
    Publication date: February 5, 2004
    Inventors: Kevin Ray, Anthony Paul Kitson, Jian Bing Huang
  • Publication number: 20040005506
    Abstract: A radiation sensitive dielectric constant changing composition comprising (A) a decomposable compound, (B) a nondecomposable compound, (C) a radiation sensitive decomposer and (D) a stabilizer.
    Type: Application
    Filed: April 1, 2003
    Publication date: January 8, 2004
    Inventors: Isao Nishimura, Nobuo Bessho, Atsushi Kumano, Kenji Yamada
  • Patent number: 6673706
    Abstract: A photoresist pattern is formed, without being exposed, by using photoresist having a residual layer proportion characteristic by which the photoresist dissolves at a suitable rate in a developing solution. First, a target layer to be patterned and a photoresist layer are sequentially formed on a substrate having a pattern that defines a step on the substrate. Some of the photoresist layer is treated with the developing solution, to thereby form a photoresist pattern whose upper surface is situated beneath the step and hence, exposes part of the target layer. Next, the exposed part of the target layer, and the photoresist pattern are removed. A silicidation process may be carried out thereafter on the area(s) from which the target layer has been removed. The method is relatively simple because it does not involve an exposure process. Furthermore, the method can be used to manufacture devices having very fine linewidths, i.e.
    Type: Grant
    Filed: December 21, 2001
    Date of Patent: January 6, 2004
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Ji-yong Yoo, Dae-youp Lee, Jeung-woo Lee, Suk-joo Lee, Jae-han Lee
  • Patent number: 6670090
    Abstract: The present invention relates to a positive-working photosensitive composition comprising a partially diazonaphthoquinone (DNQ) capped polyamic ester with a capping level of about 5-80 molar %; a photosensitive agent and a solvent. The composition shows a high photosensitivity and leaves a relief pattern with high resolution and low dark film loss.
    Type: Grant
    Filed: September 3, 2002
    Date of Patent: December 30, 2003
    Assignee: Industrial Technology Research Institute
    Inventors: Steve Lien-Chung Hsu, Jinn-Shing King, Po-I Lee, Jhy-Long Jeng
  • Patent number: 6667137
    Abstract: Infra-red absorbing polymers useful in imageable products and the lithographic printing field comprise infra-red absorbing groups carried as pendent groups on a polymer backbone. Certain infra-red absorbing groups may also act to insolublize the polymer in a developer, until it is imagewise exposed to infra-red radiation. The resulting heat renders the polymer soluble in the developer. Imageable products employing the infra-red absorbing polymers may include positive working lithographic printing plates.
    Type: Grant
    Filed: December 30, 2002
    Date of Patent: December 23, 2003
    Assignee: Kodak Polychrome Graphics LLC
    Inventors: Eduard Kottmair, Hans-Horst Glatt, Stefan Hilgart, Paul West
  • Patent number: 6645689
    Abstract: A radiation-sensitive composition for use in printing plates is described. The composition comprises: (a) at least one novolak; (b) at least one naphthoquinone diazide derivative; and (c) a copolymer comprising units A, B, and a unit C comprising a cyclic terminal urea group, wherein unit A is present in an amount of about 5 to about 50 mol % and has the formula wherein R1 is selected such that the homopolymer of A is alkali-soluble, unit B is present in an amount of about 20 to about 70 mol % and has the following formula wherein R2 is selected such that the homopolymer of B has a glass transition temperature greater than 100° C., preferably a glass transition temperature in the range from about 100 to about 380° C.
    Type: Grant
    Filed: March 13, 2002
    Date of Patent: November 11, 2003
    Assignee: Kodak Polychrome Graphics LLC
    Inventor: Mathias Jarek
  • Patent number: 6635400
    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: Grant
    Filed: April 17, 2001
    Date of Patent: October 21, 2003
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Hideto Kato, Kazuhiro Nishikawa, Yoshinori Hirano, Katsuya Takemura
  • Publication number: 20030194635
    Abstract: The present invention provides a positive working imageable composition, which includes a hydroxyfunctional resin comprising a covalently bound radiation sensitive group capable of increasing the solubility of the imageable composition in an alkaline developer upon exposure to radiation; and an isocyanate crosslinking agent. The present invention further provides an imageable element, which includes a substrate and an imageable composition according to the present invention coated on a surface of the substrate and a method of producing an imaged element according to the present invention. Also provided is a radiation sensitive hydroxyfunctional resin including a covalently bound radiation sensitive group capable of increasing solubility in an alkaline developer of an imageable composition derived therefrom upon exposure of the imageable composition to radiation.
    Type: Application
    Filed: January 24, 2002
    Publication date: October 16, 2003
    Applicant: KODAK POLYCHROME GRAPHICS, L.L.C.
    Inventor: James Mulligan
  • Publication number: 20030194633
    Abstract: A radiation-sensitive composition for use in printing plates is described.
    Type: Application
    Filed: March 13, 2002
    Publication date: October 16, 2003
    Inventor: Mathias Jarek
  • Publication number: 20030165779
    Abstract: Infra-red absorbing polymers useful in imageable products and the lithographic printing field comprise infra-red absorbing groups carried as pendent groups on a polymer backbone. Certain infra-red absorbing groups may also act to insolublize the polymer in a developer, until it is imagewise exposed to infra-red radiation. The resulting heat renders the polymer soluble in the developer. Imageable products employing the infra-red absorbing polymers may include positive working lithographic printing plates.
    Type: Application
    Filed: December 30, 2002
    Publication date: September 4, 2003
    Applicant: KODAK POLYCHROME GRAPHICS, LLC
    Inventors: Eduard Kottmair, Hans-Horst Glatt, Stefan Hilgart, Paul West
  • Publication number: 20030099888
    Abstract: A coating solution useful in the preparation of printing plate precursors comprises:
    Type: Application
    Filed: July 5, 2001
    Publication date: May 29, 2003
    Applicant: Kodak Polychrome Graphics L.L.C.
    Inventor: Mathias Jarek
  • 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
  • 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
  • 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: 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: 6506533
    Abstract: Infra-red absorbing polymers useful in imageable products and the lithographic printing field comprise infra-red absorbing groups carried as pendent groups on a polymer backbone. Certain infra-red absorbing groups may also act to insolublize the polymer in a developer, until it is imagewise exposed to infra-red radiation. The resulting heat renders the polymer soluble in the developer. Imagable products employing the infra-red absorbing polymers may include positive working lithographic printing plates.
    Type: Grant
    Filed: June 7, 2000
    Date of Patent: January 14, 2003
    Assignee: Kodak Polychrome Graphics LLC
    Inventors: Eduard Kottmair, Hans-Horst Glatt, Stefan Hilgart, Paul West
  • 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: 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: 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: 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: 6437058
    Abstract: A polymer in the form of a novolac resin is provided wherein the novolac resin has a weight average molecular weight of 1,000-30,000, some of the hydrogen atoms of hydroxyl groups are replaced by 1,2-naphthoquinonediazidosulfonyl ester groups, and some of the hydrogen atoms of the remaining hydroxyl groups are replaced by substituted acetal groups and/or crosslinked within a molecule or between molecules with crosslinking groups having C—O—C linkages. The polymer is formulated into a positive resist composition having improved uniformity, sensitivity, resolution and pattern profile as well as improved heat resistance, film retention, substrate adhesion and storage stability.
    Type: Grant
    Filed: February 7, 2001
    Date of Patent: August 20, 2002
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Tomoyoshi Furihata, Hideto Kato, Yoshinori Hirano
  • 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
  • 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: 6391513
    Abstract: The positive-working radiation sensitive resin composition which has high sensitivity, high resolution and no residues in development and ability to form a pattern having a good profile. The positive-working radiation sensitive resin composition contains a mixed radiation sensitive novolak resin comprising the mixture of 1,2-naphthoquinonediazide-4-sulfonic acid ester of an alkali soluble novolak resin and 1,2-naphthoquinonediazide-5-sulfonic acid ester of an alkali soluble novolak resin, wherein the ratio by weight of the 1,2-naphthoquinonediazide-4-sulfonyl group and 1,2-naphthoquinonediazide-5-sulfonyl group ranges from 5:95 to 20:80.
    Type: Grant
    Filed: March 16, 2001
    Date of Patent: May 21, 2002
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Kenji Susukida, Masato Nishikawa, Akio Arano
  • Publication number: 20020048714
    Abstract: A support for a lithographic printing plate with no damage in appearance such as unevenness in the form of streaks and with excellent pit homogeneity. A support for a lithographic printing plate obtained by subjecting a surface of an aluminum alloy plate to a surface treatment including alkali etching and an electrochemical graining treatment, wherein the aluminum alloy plate shows dispersion of 50% or lower for each element, the dispersion being defined by an specific equation with regard to contents of Fe, Si, Mn, Mg and Sn in a surface layer portion thereof which is from the surface to a depth of 1 &mgr;m.
    Type: Application
    Filed: September 6, 2001
    Publication date: April 25, 2002
    Inventors: Hirokazu Sawada, Atsuo Nishino, Akio Uesugi
  • 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: 6368774
    Abstract: A radiation sensitive composition comprising (A), a mixture of an isoindolinone pigment and a yellow organic pigment, (B) an alkali-soluble resin, (C) a polyfunctional monomer and (D) a photopolymerization initiator. The composition is useful for production of an additive or subtractive color filter which is used in a reflection-type color liquid crystal display device.
    Type: Grant
    Filed: June 2, 2000
    Date of Patent: April 9, 2002
    Assignee: JSR Corporation
    Inventors: Kouichi Sakurai, Hiroaki Nemoto, Atsushi Kumano
  • 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
  • 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: 6242151
    Abstract: The invention provides a novel polymer in the form of a novolac resin in which some of the hydrogen atoms of the hydroxyl groups are replaced by 1,2-naphthoquinonediazidosulfonyl ester groups and some of the hydrogen atoms of the remaining hydroxyl groups are replaced by substituted carbonyl or sulfonyl groups. The polymer has a weight average molecular weight calculated as polystyrene of 1,000-30,000. The polymer is formulated into a resist composition having improved uniformity, sensitivity, resolution and pattern geometry in microfabrication.
    Type: Grant
    Filed: August 11, 1999
    Date of Patent: June 5, 2001
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Tomoyoshi Furihata, Hideto Kato, Satoshi Okazaki
  • 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: 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: 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: 6210855
    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: December 14, 1999
    Date of Patent: April 3, 2001
    Assignee: Shin Etsu Chemical Co., Ltd.
    Inventors: Takafumi Ueda, Hideto Kato, Toshihiko Fujii, Miki Kobayashi
  • Patent number: 6200727
    Abstract: A positive photosensitive composition comprising an alkali-soluble resin having phenolic hydroxyl groups (a) and a photo-thermal conversion material (b), and not containing a quinonediazide compound, which contains an alkali-soluble resin having phenolic hydroxyl groups, of which at least some are esterified (a-1).
    Type: Grant
    Filed: February 4, 1999
    Date of Patent: March 13, 2001
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Toshiyuki Urano, Akihisa Murata, Etsuko Hino
  • Patent number: 6177225
    Abstract: A positive photosensitive resin composition. The composition comprising: (a) a capped polybenzoxazole precursor polymer having the structure; wherein Ar1 is a tetravalent aromatic group, aliphatic group, heterocylic group, or mixtures thereof; Ar2 is a divalent aromatic, heterocyclic, alicyclic, or aliphatic group that optionally may contain silicon; Ar3 is divalent aromatic group, aliphatic group, heterocyclic group, or mixtures thereof; Z is one of the following groups: x is 10 to 1000; y is 0 to 900; and b is 0.10 to 350; (b) a photosensitive agent; and (c) a solvent.
    Type: Grant
    Filed: September 24, 1999
    Date of Patent: January 23, 2001
    Assignee: Arch Specialty Chemicals, Inc.
    Inventors: William D. Weber, Pamela J. Waterson, Steve Lien-Chung Hsu, Ahmad Naiini