Radiation-sensitive Composition Patents (Class 430/170)
  • Patent number: 5726295
    Abstract: A new class of 3,4-dihydrocoumarin derivatives which are useful as photoactive compounds in a wide variety of applications including photoresists and other opto-electronic applications are disclosed and claimed. Preferred embodiments include ether, ester, carbonate, and sulfonate derivatives of 5-hydroxy, 6-hydroxy, and 7-hydroxy-3-diazo-4-oxo-3,4-dihydrocoumarins. These compounds exhibit very high photosensitivity in the deep ultraviolet (DUV) region (ca. 250 nm), and therefore, are useful as photoactive compounds in DUV photoresist formulations.
    Type: Grant
    Filed: March 7, 1997
    Date of Patent: March 10, 1998
    Assignee: Hoechst Celanese Corp.
    Inventors: Mohammad Aslam, Michael T. Sheehan, Debasish Kuila
  • Patent number: 5705317
    Abstract: A radiation-sensitive mixture which contains (a) a compound of the formula (I) ##STR1## where R.sup.1 is an optionally substituted alkyl radical, R.sup.2 is a hydrogen atom or an optionally substituted alkyl radical containing 1 to 4 carbon atoms, R.sup.3 is an n-valent, optionally polymeric aliphatic or aromatic radical and n is a number from 1 to 100; and b) a compound which forms a strong acid on exposure to actinic radiation.
    Type: Grant
    Filed: December 5, 1995
    Date of Patent: January 6, 1998
    Assignee: AGFA-Gevaert AG
    Inventors: Mathias Eichhorn, Gerhard Buhr
  • Patent number: 5695910
    Abstract: A resist composition for deep ultraviolet light comprising (a) one of the following resin components (i)-(iii): (i) a resin which becomes alkali-soluble by eliminating protective groups by the action of an acid, (ii) a combination of an alkali-soluble resin and a dissolution-inhibiting compound, and (iii) a combination of an alkali-soluble resin and a crosslinkable compound, (b) an acid generater, (c) a special anthracene derivative, and (d) a solvent, is suitable for forming a pattern using deep ultraviolet light, KrF excimer laser light, etc., on a highly reflective substrate having level differences due to absorption of undesirable reflected deep ultraviolet light.
    Type: Grant
    Filed: August 26, 1996
    Date of Patent: December 9, 1997
    Assignees: Wako Pure Chemical Industries, Ltd., Matsushita Electrical Industrial Co., Ltd.
    Inventors: Fumiyoshi Urano, Takanori Yasuda, Akiko Katsuyama, Kazuhiro Yamashita
  • Patent number: 5693451
    Abstract: The present invention relates to a single or multi-layer recording material for recording images or data, which material has at least one layer sensitive to light or to heat of a plastic containing a pyrrole compound or a pyrrole oligomer.
    Type: Grant
    Filed: September 23, 1994
    Date of Patent: December 2, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Alexa Sommer, Udo Herrmann, Robert Bloodworth, Gunther Penners, Klaus Sommer
  • Patent number: 5691100
    Abstract: A material for the formation of a pattern is provided which has a wide exposure latitude and is less liable to cause a dimensional change of a pattern with a change in exposure. The material comprises (A) a compound having a capability of producing an acid upon irradiation with an active beam, (B) a compound capable of producing a base or increasing its basicity, (C) a compound having at least one bond clearable with an acid and/or (D) a compound insoluble in water but soluble in an aqueous alkaline solution.
    Type: Grant
    Filed: March 29, 1996
    Date of Patent: November 25, 1997
    Assignee: Hoechst Japan Limited
    Inventors: Takanori Kudo, Seiya Masuda, Yoshiaki Kinoshita, Klaus Przybilla, Natsumi Endo, Natsumi Suehiro, Hiroshi Okazaki
  • Patent number: 5688628
    Abstract: A resist composition comprising in admixture (A) a compound which forms an acid upon exposure to active rays, (B) a polymer which has at least one structural unit with a group unstable to an acid and cleaves at this group in the presence of the acid derived from the compound (A) to turn alkali-soluble, and (C) a phenolic compound, and a process for forming a resist pattern using this resist composition are provided.
    Type: Grant
    Filed: November 10, 1994
    Date of Patent: November 18, 1997
    Assignee: Nippon Zeon Co., Ltd.
    Inventors: Masayuki Oie, Nobunori Abe, Hideyuki Tanaka, Akira Oikawa, Shuichi Miyata
  • Patent number: 5670299
    Abstract: A resist composition comprising (a) a polymer having at least repeating units of the formulae: ##STR1## (b) a photoacid generator and (c) a solvent, has high sensitivity to light, excellent heat resistance, adhesiveness to a substrate and suitable for pattern formation with high resolution.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: September 23, 1997
    Assignee: Wako Pure Chemical Industries, Ltd.
    Inventors: Fumiyoshi Urano, Hirotoshi Fujie, Keiji Oono, Takaaki Negishi
  • Patent number: 5663035
    Abstract: A radiation-sensitive mixture for use in the production of semiconductor elements, which has high sensitivity and high resolution, which can be developed by an aqueous alkaline solution, and which is based on a novel concept in that a stable acid latent image is controlled by using a radiation-decomposable base.The mixture is characterized by comprising as essential components a) a binder which is insoluble in water but soluble in an aqueous alkaline solution; b.sup.1) a compound having at least one bond which can be cleaved by an acid, or b.sup.2) a compound having at least one bond which is crosslinked with the compound a) by an acid; c) a compound which generates an acid when irradiated; and d) a basic iodonium compound.
    Type: Grant
    Filed: April 12, 1995
    Date of Patent: September 2, 1997
    Assignee: Hoechst Japan Limited
    Inventors: Seiya Masuda, Munirathna Padmanaban, Takanori Kudo, Yoshiaki Kinoshita, Natsumi Suehiro, Yuko Nozaki, Hiroshi Okazaki, Klaus Jurgen Przybilla
  • Patent number: 5654121
    Abstract: The invention relates to a positive-working radiation-sensitive mixture containing a) a polymeric binder having acid-labile groups and b) a compound which forms a strong acid on irradiation, in which the binder simultaneously contains units of the formulae I, II and IIIR.sup.1 --OH (I) ,R.sup.1 --O--CO.sub.2 R.sup.2 (II)R.sup.1 --O--CH.sub.2 --CHR.sup.3 --OH (III).The mixture is used to coat radiation-sensitive recording material which can be used to produce printing plates and photoresists.
    Type: Grant
    Filed: April 27, 1995
    Date of Patent: August 5, 1997
    Assignee: Agfa-Gevaert AG
    Inventors: Mathias Eichhorn, Gerhard Buhr
  • Patent number: 5648195
    Abstract: A radiation-sensitive resist composition for manufacturing highly resolved relief structures is characterized by the following components:a film-forming base polymer;a radiation-active component that releases an acid when irradiated;a radiation-sensitive ester-former; anda solvent.
    Type: Grant
    Filed: January 5, 1995
    Date of Patent: July 15, 1997
    Assignee: Siemens Aktiengesellschaft
    Inventors: Michael Sebald, Siegfried Birkle, Karin Preissner, Hans-Jurgen Bestmann
  • Patent number: 5627006
    Abstract: A photoresist composition comprising (a) a difficultly alkali-soluble special resin, (b) a photo-sensitive compound capable of generating a carboxylic acid, and (c) a solvent, is effective for pattern formation using deep ultraviolet light, KrF excimer laser beams, etc.
    Type: Grant
    Filed: April 18, 1995
    Date of Patent: May 6, 1997
    Assignees: Wako Pure Chemical Industries, Ltd., Matsushita Electric Industrial Co., Ltd.
    Inventors: Fumiyoshi Urano, Keiji Oono, Hirotoshi Fujie
  • Patent number: 5624788
    Abstract: Disclosed are an organic silicon compound having a repeating unit represented by general formula (I) shown below, a resist, a thermal polymerization composition and a photopolymerization composition containing the organic silicon compound, ##STR1## wherein R.sup.1 is a t-butyl group or a tetrahydropyranyl group, R.sup.2 is an hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, a substituted or unsubstituted aryl group having 1 to 24 carbon atoms, or a substituted or unsubstituted aralkyl having 7 to 24 carbon atoms, R.sup.3 is a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 24 carbon atoms or an alkoxyl group, and k represents an integer from 0 to 4.
    Type: Grant
    Filed: June 15, 1995
    Date of Patent: April 29, 1997
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Shinji Murai, Yoshihiko Nakano, Ken Uchida, Shuji Hayase
  • Patent number: 5585217
    Abstract: Disclosed herein is a polyamic acid composition which comprises an aromatic carboxylic acid compound having phenolic hydroxyl groups, polyamic acid, and a photosensitizer made of a diazide compound, and which can form a polyimide film pattern having a high resolution and capable of firmly adhering to a substrate.
    Type: Grant
    Filed: May 30, 1995
    Date of Patent: December 17, 1996
    Assignee: Kabushiki Kaisha Toshiba
    Inventor: Masayuki Oba
  • Patent number: 5582952
    Abstract: A photosensitive lithographic printing plate which provides a wide range of proper conditions for development, high impression capacity, a flexible film sufficient in adhesion to a support and excellent processing suitability with a weakly alkaline developer (pH 12.5 or less) is disclosed. The photosensitive lithographic printing plate comprises a support and a photosensitive layer provided thereon, wherein the photosensitive layer is formed from a photosensitive composition containing at least a two-equivalent coupler residue-containing compound and a photosensitive compound or a photosensitive mixture acting as a positive type.
    Type: Grant
    Filed: March 7, 1995
    Date of Patent: December 10, 1996
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Koichi Kawamura, Keiji Akiyama, Toshifumi Inno, Katsuji Kitatani
  • Patent number: 5558976
    Abstract: A resist material comprising (a) a terpolymer, (b) a photoacid generator, and (c) a solvent has high light sensitivity, heat resistance, adhesiveness, resolution, etc., and is suitable for forming a pattern of rectangular shape.
    Type: Grant
    Filed: November 29, 1995
    Date of Patent: September 24, 1996
    Assignees: Wako Pure Chemical Industries, LTD., Matsushita Electric Industrial Co., LTD.
    Inventors: Fumiyoshi Urano, Takaaki Negishi, Akiko Katsuyama, Masayuki Endo
  • Patent number: 5558971
    Abstract: A resist material comprising (a) a terpolymer, (b) a photoacid generator, and (c) a solvent has high light sensitivity, heat resistance, adhesiveness, resolution, etc., and is suitable for forming a pattern of rectangular shape.
    Type: Grant
    Filed: March 21, 1995
    Date of Patent: September 24, 1996
    Assignees: Wako Pure Chemical Industries, Ltd., Matsushita Electric Industrial Co., Ltd.
    Inventors: Fumiyoshi Urano, Takaai Negishi, Akiko Katsuyama, Masayuki Endo
  • Patent number: 5543265
    Abstract: Changing (varying, irregular) resist thickness on semiconductor wafers having irregular top surface topography or having different island sizes, affects the percent reflectance (and absorption efficiency) of incident photolithographic light, and consequently the critical dimensions of underlying features being formed (e.g., polysilicon gates). A low solvent content resist solution that can be applied as an aerosol provides a more uniform thickness resist film, eliminating or diminishing photoresist thickness variations. A top antireflective coating (TAR) also aids in uniformizing reflectance, despite resist thickness variations. The two techniques can be used alone, or together. Hence, better control over underlying gate size can be effected, without differential biasing.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: August 6, 1996
    Assignee: LSI Logic Corporation
    Inventor: Mario Garza
  • Patent number: 5525453
    Abstract: A novel positive-working radiation-sensitive mixture having a high sensitivity to radiation in a short-wavelength UV region is provided which can be developed in an aqueous alkaline solution, has a stable acid latent image and is used for the production of a semiconductor. The mixture comprises, as indispensable components, a) a binder insoluble in water but soluble in an aqueous alkaline solution, b) a compound having at least one bond cleavable with an acid, c) a compound capable of producing an acid upon radiation, and d.sub.1) a basic ammonium compound or d.sub.2) a basic sulfonium compound.
    Type: Grant
    Filed: February 15, 1994
    Date of Patent: June 11, 1996
    Assignee: Hoechst Japan Limited
    Inventors: Klaus J. Przybilla, Takanori Kudo, Seiya Masuda, Yoshiaki Kinoshita, Natumi Suehiro, Munirathna Padmanaban, Hiroshi Okazaki, Hajime Endo, Ralph Dammel, Georg Pawlowski
  • Patent number: 5476751
    Abstract: The invention relates to compounds of formula I ##STR1## wherein A is a radical of formula ##STR2## R.sub.1 and R.sub.2 are each independently of the other hydrogen, C.sub.1 --C.sub.4 alkyl, C.sub.1 C.sub.4 alkoxy, halogen or a radical of formula ##STR3## wherein X is --O--, --CH.sub.2 --, --C(CH.sub.3).sub.2 -- or --SO.sub.2 --, and R.sub.3 and R.sub.4 are each independently of the other hydrogen, C.sub.1 --C.sub.4 alkyl or phenyl, as well as compositions comprising these compounds.The compositions are particularly suitable for making integrated circuits.
    Type: Grant
    Filed: October 14, 1994
    Date of Patent: December 19, 1995
    Assignee: Ciba-Geigy Corporation
    Inventor: Alfred Steinmann
  • Patent number: 5468589
    Abstract: A resist composition comprising (a) a polymer having at least repeating units of the formulae: ##STR1## (b) a photoacid generator and (c) a solvent, has high sensitivity to light, excellent heat resistance, adhesiveness to a substrate and suitable for pattern formation with high resolution.
    Type: Grant
    Filed: June 15, 1992
    Date of Patent: November 21, 1995
    Assignees: Wako Pure Chemical Industries, Ltd., Matsushita Electric Industrial Co., Ltd.
    Inventors: Fumiyoshi Urano, Hirotoshi Fujie, Keiji Oono, Takaaki Negishi
  • Patent number: 5424166
    Abstract: A negative-working radiation-sensitive mixture which comprisesa) a compound, which forms a strong acid on irradiation, of the general formula ##STR1## in which R.sup.1 is a radical R.sup.2 --SO.sub.2 -- or R.sup.3 --C(O)-- andR.sup.2 and R.sup.3 independently of one another are an optionally substituted alkyl, cycloalkyl, aryl or heteroaryl radical,b) a compound containing at least two reactive groups which can be crosslinked by an acid andc) a water-insoluble binder which is soluble or at least swellable in aqueous-alkaline solutions, is described.The radiation-sensitive mixture according to the invention is distinguished by a high sensitivity over a wide spectral range. It likewise exhibits a high heat stability and forms no corrosive photolysis products on exposure to light.
    Type: Grant
    Filed: February 4, 1994
    Date of Patent: June 13, 1995
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Georg Pawlowski, Ralph Dammel, Horst Roeschert, Walter Spiess, Winfried Meier
  • Patent number: 5389491
    Abstract: A negative working resist composition comprising (a) an alkali-soluble resin, (b) an aromatic compound having at least two groups of the formula: --OCH.sub.2 OR.sup.1 wherein R.sup.1 is alkyl or aralkyl, (c) a photoacid generator, and (d) a solvent, can form fine patterns with high resolution when exposed to deep UV, KrF excimer laser light, etc. due to high light transmittance and high sensitivity.
    Type: Grant
    Filed: June 28, 1993
    Date of Patent: February 14, 1995
    Assignees: Matsushita Electric Industrial Co., Ltd., Wako Pure Chemical Industries, Ltd.
    Inventors: Yoshiyuki Tani, Masayuki Endo, Fumiyoshi Urano, Takanori Yasuda
  • Patent number: 5350660
    Abstract: A resist material comprising (a) a polymer having a monomer unit having a special functional group, a monomer unit having a phenolic hydroxyl group, and if necessary a third monomer unit, (b) a photoacid generator, and (c) a solvent can provide a resist film excellent in heat resistance and adhesiveness to a substrate when exposed to light with 300 nm or less such as deep UV light, KrF excimer laser light, etc., and is suitable for forming ultrafine patterns.
    Type: Grant
    Filed: January 28, 1991
    Date of Patent: September 27, 1994
    Assignee: Wako Pure Chemical Industries, Ltd.
    Inventors: Fumiyoshi Urano, Masaaki Nakahata, Hirotoshi Fujie, Keiji Oono
  • Patent number: 5340678
    Abstract: A dry toner for developing an electrostatic latent image comprising toner particles and fine particles of a lubricant coated with an inorganic compound fine powder and an image formation method using the same. The toner is excellent in fluidity, cleaning properties, stability with environmental changes, and durability.
    Type: Grant
    Filed: June 30, 1993
    Date of Patent: August 23, 1994
    Assignee: Fuji Xerox Co., Ltd.
    Inventors: Chiaki Suzuki, Atuhiko Eguchi, Yuka Ishihara, Takayoshi Aoki, Seiichi Takagi, Toshiyuki Yano, Masao Mochizuki
  • Patent number: 5326826
    Abstract: Radiation-sensitive polymers, a mixture containing these radiation-sensitive polymers as binder, and a process for the preparation of the radiation-sensitive polymer binders are disclosed. A positive radiation-sensitive recording material containing the radiation-sensitive polymer is also disclosed.
    Type: Grant
    Filed: February 26, 1992
    Date of Patent: July 5, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Horst Roeschert, Hans-Joachim Merrem, Georg Pawlowski, Juergen Fuchs, Ralph Dammel
  • Patent number: 5227495
    Abstract: A cyanine compound of the following formula: ##STR1## wherein T.sup.1 and T.sup.2 each independently represents an atomic group which is necessary for forming a condensed benzene ring; L.sup.3 represents a methine group or a trivalent connecting group formed by conjugated double bonding of 3, 5 or 7 methine groups; R.sup.21, R.sup.22, R.sup.23 and R.sup.24 each independently represents an alkyl group having 1 to 12 carbon atoms or a phenyl group both of which may or may not be substituted; Y is an anion and q is a number which is necessary for neutralizing a positive charge; provided that at least one of R.sup.21, R.sup.22, R.sup.23 and R.sup.24 is an alkyl group having 3 or more carbon atoms and which may or may not be substituted when L.sup.3 consists of 1, 3 or 5 methine groups.The cyanine compound can be used as a coloring material, a sensitizing dye for photographic use, a recording dye for use in optical information recording media, a staining agent, a pharmaceutical agent, and the like.
    Type: Grant
    Filed: January 10, 1991
    Date of Patent: July 13, 1993
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Yoshio Inagaki, Masao Yabe
  • Patent number: 5204225
    Abstract: Selected photosensitive compounds activated by deep ultraviolet radiation or x-rays and capable of being employed at very low concentrations in photosensitive compositions are provided for producing thermally stable and aqueously developable, negative images on surfaces. The selected photosensitive compounds are halogenated organic compounds, including 1,1-bis[p-chlorophenyl]-2,2,2-trichloroethane, which generate an inorganic halogen acid upon exposure to deep UV or other short wavelength radiations. They may be used at concentrations of less than 5 weight percent of the total solids content of the photosensitive composition to produce aqueously developable negative images using deep UV exposure.
    Type: Grant
    Filed: April 23, 1991
    Date of Patent: April 20, 1993
    Assignee: Rohm and Haas Company
    Inventor: Wayne E. Feely
  • Patent number: 5171656
    Abstract: Photosensitive compositions comprising a polymer and a photoactive constituent, which are able to be developed with aqueous, alkaline agents exhibit good bleaching properties in the DUV range, whereby the photoactive constituent has good solubility-inhibiting properties and does not evaporate during the drying process, when the photoactive constituent comprises diazo tetronic acid or a diazo tetronic acid derivative of the following structure: ##STR1## where the residues R are the same or different and signify H, alkyl, cycloalkyl, aryl or a silicon-containing residue.
    Type: Grant
    Filed: July 20, 1990
    Date of Patent: December 15, 1992
    Assignee: Siemens Aktiengesellschaft
    Inventors: Michael Sebald, Juergen Beck, Rainer Leuschner, Recai Sezi, Hans J. Bestmann
  • Patent number: 5130392
    Abstract: Radiation-sensitive polymers suitable for use in positive- and negative-working recording elements contain not only acid-labile groups but also onium salt groups having nonnucleophilic counterions in one and the same molecule.
    Type: Grant
    Filed: January 9, 1990
    Date of Patent: July 14, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Reinhold Schwalm, Andreas Boettcher
  • Patent number: 5084372
    Abstract: A light-sensitive composition for the preparation of printing plates is described, which contains a water-insoluble binder which is soluble in aqueous-alkaline solutions; a light-sensitive component which is an o- or p-quinone diazide, a diazonium salt polycondensation product or a mixture ofa) a compound which eliminates an acid on exposure to light andb) a compound having at least one C--O--C group which can be split by acid; and a thermo-crosslinking compound which is a cyclical acid amide of the general formula: ##STR1## wherein R denotes a hydrogen atom or an alkyl group. The printing plates can be baked at lower temperatures than plates without a crosslinking agent, but nevertheless have a long shelf life.
    Type: Grant
    Filed: January 23, 1991
    Date of Patent: January 28, 1992
    Assignee: Hoechst Celanese Corporation
    Inventors: Shane Hsieh, Paul Stahlhofen
  • Patent number: 5049477
    Abstract: A radiation responsive composition containing a compound represented by the following formula (I) and a photoreducing agent capable of forming a redox couple together with said compound for many uses, e.g., image formation, etching, plating, etc.: ##STR1## wherein N represents a nitrogen atom; X represents an oxygen atom (--O--), a sulfur atom (--S--), or a nitrogen-containing group of formula, ##STR2## R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each represents a mere bond, a substituted or unsubstituted alkyl, aryl, heterocyclic, acyl, aralkyl, alkenyl, alkynyl or carbamoyl group, or a sulfonyl group into which a substituted or unsubstituted alkyl or aryl group has been introduced, provided that at least one of the substituents R.sup.1 to R.sup.3 be a substituted or unsubstituted aryl or heterocyclic group and that two or more of R.sup.1, R.sup.2 and R.sup.3, or of R.sup.1, R.sup.2, R.sup.3 and R.sup.
    Type: Grant
    Filed: April 14, 1989
    Date of Patent: September 17, 1991
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Koki Nakamura, Masayoshi Tsuboi, Keizo Koya
  • Patent number: 5028109
    Abstract: A method of fabricating a periodic nonlinear optic radiation modulation zone within a polymeric waveguide structure. The method includes the steps of (a) providing a layer of a polymeric material having an optically active material that is orientable by an electrical field; (b) applying an electrical field to the layer for orienting at least a portion of the optically active material; and (c) photopolymerizing at least a portion of the polymeric layer for fixing the oriented optically active material into the oriented position. In accordance with one embodiment the step of photopolymerizing includes the steps of (d) generating a diffraction pattern within the polymeric layer, the diffraction pattern being characterized by bright and dark fringes; and (e) photoplymerizing a volume of the polymeric layer within substantially only portions thereof that correspond to the bright fringes.
    Type: Grant
    Filed: January 26, 1990
    Date of Patent: July 2, 1991
    Inventor: Nabil M. Lawandy
  • Patent number: 5008175
    Abstract: A light-sensitive composition for the preparation of printing plates is described, which contains a water-insoluble binder which is soluble in aqueous-alkaline solutions; a light-sensitive component which is an o- or p- quinone diazide, a diazonium salt polycondensation product or a mixture of(a) a compound which eliminates an acid on exposure to light and(b) a compound having at least one C--O--C group which can be split by acid; and a thermo-crosslinking compound which is a cyclical acid amide of the general formula: ##STR1## wherein R denotes a hydrogen atom or an alkyl group. The printing plates can be baked at lower temperatures than plates without a crosslinking agent, but nevertheless have a long shelf life.
    Type: Grant
    Filed: February 16, 1990
    Date of Patent: April 16, 1991
    Assignee: Hoechst Celanese Corporation
    Inventors: Shane Hsieh, Paul Stahlhofen
  • Patent number: 4996301
    Abstract: Polyfunctional .alpha.-diazo-.beta.-keto esters of the general formula I are described ##STR1## in which R.sup.1 denotes an aliphatic, cycloaliphatic or araliphatic or aromatic radical having 4 to 20 carbon atoms, in which individual CH.sub.2 groups can be replaced by oxygen or sulfur atoms or by N-- or NH groups and/or contain keto groups,X denotes an aliphatic, cycloaliphatic, carbocyclic, heterocyclic or araliphatic radical having 2 to 22 carbon atoms, in which individual CH.sub.2 groups can be replaced by oxygen or sulfur atoms or by the groups ##STR2## in which R.sup.2 and R.sup.3 independently of one another represent hydrogen or an aliphatic, carbocyclic or araliphatic radical,m denotes an integer from 2 to 10 andn denotes an integer from 0 to 2,whereinm-n is .gtoreq.2.The compounds mentioned are used as photoactive components in radiation-sensitive mixtures.
    Type: Grant
    Filed: January 12, 1990
    Date of Patent: February 26, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Peter Wilharm, Hans-Joachim Merrem, Georg Pawlowski
  • Patent number: 4994530
    Abstract: Polymeric compounds comprise groups of the formula ##STR1## attached to carbon atoms of a polymer containing hydroxyl and optionally epoxide groups wherein X is ##STR2## The compounds are produced by reacting a starting polymer, which contains hydroxy groups and optionally epoxide groups with a reagent containing a cyclic anhydride group and a further functional group capable of reacting with the hydroxyl (and/or epoxide) groups preferentially to the anhydride group. The compounds are useful as bakeable support resins for radiation sensitive compounds in the production of printing plates.
    Type: Grant
    Filed: November 22, 1989
    Date of Patent: February 19, 1991
    Assignee: E. I. Du Pont de Nemours and Company (Inc.)
    Inventors: Terence Etherington, Victor Kolodziejczyk
  • Patent number: 4986921
    Abstract: This invention relates to a photosensitizer which is bound to a cellulose acetate polymer, a method of preparing the bound photosensitizer and a process for using the bound photosensitizer. The photosensitizers which may be used in the invention include rose bengal, rhodamine B, acridine orange, methylene blue and zinc phthalocyanine. The photosensitizer is attached to the cellulose acetate by reacting an acid group on the photosensitizer with a hydroxyl group. Finally, the bound photosensitizer may be used to oxidize undesirable oxidizable compounds present in a hydrocarbon or aqueous fraction. One specific example is the sweetening of kerosene which involves oxidizing the mercaptans contained in the kerosene.
    Type: Grant
    Filed: August 29, 1990
    Date of Patent: January 22, 1991
    Assignee: Allied-Signal Inc.
    Inventors: Stephen F. Yates, Mary L. Good, Inara M. Brubaker
  • Patent number: 4977511
    Abstract: A process for making three dimensional models is disclosed which is characterized in that a photohardenable composition is used which comprises a free radical addition polymerizable or crosslinkable compound and an ionic dye-counter ion compound, said compound being capable of absorbing actinic radiation and producing free radicals which initiate free radical polymerization or crosslinking of said compound.
    Type: Grant
    Filed: April 13, 1988
    Date of Patent: December 11, 1990
    Assignee: The Mead Corporation
    Inventors: Peter Gottschalk, Douglas C. Neckers, Gary B. Schuster, Paul C. Adair, S. Peter Pappas
  • Patent number: 4968586
    Abstract: A negative-working imaging composition suitable for use as a dry film resist, comprises, in admixture, (a) a polymeric binder, (b) a Co (III) compound capable of partial reduction to Co (II) upon exposure to activating radiation, and (c) a redox transfer ligand capable of reacting with Co (II) to form a Co (II) chelate which reduces adjacent remaining Co (III) compound and forms a Co (III) chelate effective to provide imagewise differential solubility to the composition. The composition can be imagewise exposed to activating radiation, such as a laser, heated, and developed with a developer to form a resist image in the exposed areas. An element comprising a support and a layer of the above-described composition is particularly useful in the manufacture of printed circuit boards by laser direct imaging.
    Type: Grant
    Filed: December 14, 1989
    Date of Patent: November 6, 1990
    Assignee: Eastman Kodak Company
    Inventor: Thap DoMinh
  • Patent number: 4957847
    Abstract: A heat-sensitive recording material comprising a base and, on top of the said base, a heat-sensitive layer containing a cyclic diazo component and a coupling component, the cyclic diazo component being a benzotriazine compound of the formula ##STR1## wherein Q is --CH.sub.2 --, --CO-- or --SO.sub.2 --, R is hydrogen, hydroxyl, or aryl or alkenyl, each unsubstituted or substituted by halogen, hydroxyl, cyano, lower alkoxy, lower alkylthio, acyloxy, lower alkoxycarbonyl or lower alkylsulfonyl, or is acyl, acyloxy or acylamino, cycloalkyl, or is aryl or aralkyl such as phenyl, phenylalkyl or naphthyl each unsubstituted or substituted on the ring by cyano, halogen, nitro, trifluoromethyl, lower alkyl, lower alkylthio, lower alkoxy, lower alkylcarbonyl or lower alkoxycarbonyl, or is a heterocyclic radical, and the benzene ring A is unsubstituted or substituted by halogen, cyano, nitro, lower alkyl, lower alkoxy, lower alkylthio, lower alkylcarbonyl or lower alkoxycarbonyl.
    Type: Grant
    Filed: December 2, 1988
    Date of Patent: September 18, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Jean-Marie Adam, Hans Baumann
  • Patent number: 4937176
    Abstract: A method of manufacturing a semiconductor device, in which a layer of photolacquer (5) containing as a photoactive component a diazo oxide is provided on a semiconductor substrate. Of this layer, parts (9) are irradiated by a first patterned irradiation (7) and these parts are then rendered poorly developable by an intermediate treatment. Subsequently, the lacquer layer (5) is subjected to a second non-patterned irradiation (11) and is then developed. According to the invention, in the parts (9) irradiated by the first irradiation a pigment is formed, which absorbs radiation having a wavelength at which diazo oxide is photosensitive. The second irradiation is carried out with radiation of that wavelength. Thus, lacquer tracks having a rectangular profile can be obtained in a simple manner.
    Type: Grant
    Filed: September 27, 1988
    Date of Patent: June 26, 1990
    Assignee: U.S. Philips Corporation
    Inventors: Franciscus A. Vollenbroek, Wilhelmus P. M. Nijssen, Marcellinus J. H. J. Geomini
  • Patent number: 4877716
    Abstract: An improved developer for PMMA electron resist comprising an effective amount of MEK in combination with MIBK or CS alone or a mixture thereof.
    Type: Grant
    Filed: February 24, 1988
    Date of Patent: October 31, 1989
    Assignee: Arizona Board of Regents
    Inventors: Gary Bernstein, David K. Ferry, Wenping Liu
  • Patent number: 4865942
    Abstract: A photohardenable composition comprising a free radical addition polymerizable or crosslinkable compound and a cationic dye-borate anion complex, said complex being capable of absorbing actinic radiation and producing free radicals which initiate free radical polymerization or crosslinking of said compound; and photosensitive materials employing the composition where in one embodiment the composition is microencapsulated.
    Type: Grant
    Filed: July 20, 1988
    Date of Patent: September 12, 1989
    Assignee: The Mead Corporation
    Inventors: Peter Gottschalk, Gary B. Schuster
  • Patent number: 4840866
    Abstract: A photographic material exhibiting improved photographic characteristics comprising a photographic material comprising a support having a layer of microcapsules thereon, and an image-forming agent being associated with said microcapsules, said microcapsules including a mixture of a first subset of microcapsules and a second subset of microcapsules, said first and second subsets of microcapsules being associated with an image-forming agent for the same color, and said first subset of microcapsules providing a higher film speed than said second subset of microcapsules when said first and second subsets of microcapsules are exposed to a broad band white light source and developed under identical conditions.
    Type: Grant
    Filed: March 24, 1988
    Date of Patent: June 20, 1989
    Assignee: The Mead Corporation
    Inventors: Kerry Kovacs, William Simpson, Amy L. Burkholder, Russell K. Messer, Teresa M. Thomas
  • Patent number: 4800149
    Abstract: A photohardenable composition comprising a free radical addition polyermizable or crosslinkable compound and a cationic dye-borate anion complex, said complex being capable of absorbing actinic radiation and producing free radicals which initiate free radical polymerization of crosslinking of said compound; and photosensitive materials employing the composition where in one embodiment the composition is microencapsulated.
    Type: Grant
    Filed: February 16, 1988
    Date of Patent: January 24, 1989
    Assignee: The Mead Corporation
    Inventors: Peter Gottschalk, Gary B. Schuster
  • Patent number: 4772541
    Abstract: A photohardenable composition comprising a free radical addition polymerizable or crosslinkable compound and a cationic dye-borate anion complex, said complex being capable of absorbing actinic radiation and producing free radicals which initiate free radical polymerization or crosslinking of said compound; and photosensitive materials employing the composition where in one embodiment the composition is microencapsulated.
    Type: Grant
    Filed: October 10, 1986
    Date of Patent: September 20, 1988
    Assignee: The Mead Corporation
    Inventors: Peter Gottschalk, Gary B. Schuster
  • Patent number: 4752551
    Abstract: Photosensitive solubilization inhibitor compounds of the formula ##STR1## wherein: x is an integer equal to the valence or functionality of the radical R, andR is a radical selected from the group consisting of the residue of a mono-, di-, tri- or polyfunctional alkanol or silicon-containing alkanol and is attached to the oxy atom of the carboxyl group through a carbon atom.Positive deep ultra-violet photoresists which are base developable comprise base soluble polymers and the photosensitive solubilization inhibition agents. Lithographic resist images are formed with the deep ultra-violet photoresists upon exposure to deep ultra-violet light.
    Type: Grant
    Filed: October 2, 1986
    Date of Patent: June 21, 1988
    Assignee: J. T. Baker Inc.
    Inventor: George Schwartzkopf
  • Patent number: 4735885
    Abstract: Disclosed are substituted derivatives of 5-diazobarbituric acid selected from those having the formulas: ##STR1## wherein R.sub.1 and R.sub.2 are substituents selected from the group consisting of C.sub.3 to C.sub.12 alkyl, cyclohexyl, benzyl and C.sub.2 to C.sub.6 aralkyl groups, wherein R.sub.3 and R.sub.4 are substituents selected from the group consisting of C.sub.1 to C.sub.12 alkyl, cyclohexyl, benzyl or other C.sub.2 to C.sub.6 aralkyl groups and R.sub.5 is selected from the group consisting of .alpha.,.omega.-disubstituted C.sub.2 to C.sub.12 alkyl, methylene dicyclohexyl, or C.sub.1 to C.sub.6 dialkylphenylene.These compounds provide DUV response with an absorption maximum near 260 nm. The substituents are chosen to be nonabsorbing alkyl groups that allow efficient photobleaching of the sensitizer during exposure.The sensitizers of the present invention are designed to function in the DUV region and are useful in the manufacture of semi-conductor devices.
    Type: Grant
    Filed: December 6, 1985
    Date of Patent: April 5, 1988
    Assignee: Allied Corporation
    Inventors: Frederick R. Hopf, Michael J. McFarland
  • Patent number: 4656115
    Abstract: An improved vesicular matrix prepared by the emulsion polymerization of methacrylonitrile, either alone or with a small amount of comonomer, in the presence of a cationic emulsifier. The resulting polymer or copolymer can be used alone, or the polymer or copolymer may be blended with a small amount of a highly incompatible polymer or copolymer, to provide an improved vesicular matrix.
    Type: Grant
    Filed: November 22, 1985
    Date of Patent: April 7, 1987
    Assignee: James River Graphics, Inc.
    Inventors: Ahmad Arfaei, Everett W. Bennett
  • Patent number: 4654291
    Abstract: An improved vesicular matrix prepared by employing regulated inner incompatibility to produce enhanced nucleation. The inner incompatibility is produced by copolymerizing a first monomer with a small amount of a second monomer wherein a homopolymer of the second monomer would be incompatible with a polymer of the first monomer, or by blending a first polymer or copolymer with a small amount of a highly incompatible second polymer or copolymer.
    Type: Grant
    Filed: November 22, 1985
    Date of Patent: March 31, 1987
    Assignee: James River Graphics
    Inventor: Jan B. Suchy
  • Patent number: 4645730
    Abstract: The lithographic printing plate of the invention comprises a substrate having a hydrophilic surface, a coating on said surface of a light sensitive material (e.g., a water soluble diazo) and a top coating of discrete, oleophilic resin particles (e.g., an emulsion polymer), the resin particle coating being:(a) transparent to actinic light;(b) sufficiently permeable to allow a developer for the light sensitive material to penetrate through to the underlying light sensitive coating;(c) insoluble in said developer;(d) capable of being coalesced in situ after the plate is imaged and developed.
    Type: Grant
    Filed: September 17, 1984
    Date of Patent: February 24, 1987
    Assignee: Howard A. Fromson
    Inventors: Howard A. Fromson, Robert F. Cracia