Radiation-activated Cross-linking Agent Containing Patents (Class 430/927)
  • Patent number: 5554465
    Abstract: The present invention provides a composition having sensitivity to light or radiation. The composition comprises a polymer having a siloxane-bond structure which undergoes polymerization reaction when irridiated with light or radiation, and a sensitizing agent. The present invention also provides a process for forming a pattern, preparing a photomask and a semiconductor device by using the composition of the present invention.
    Type: Grant
    Filed: May 23, 1995
    Date of Patent: September 10, 1996
    Assignee: Matsushita Electronics Corporation
    Inventor: Hisashi Watanabe
  • Patent number: 5529885
    Abstract: Disclosed are a negative photosensitive composition comprising an alkali-soluble resin, a photo acid generating system, and a crosslinking agent for the alkali-soluble resin which acts on the resin under acidic conditions, in which the crosslinking agent is a highly-alkylated alkoxymethylmelamine resin having a monomer content of from 5 to 40% by weight, and a method for forming a negative photo-resist pattern using the composition. The resist composition is stable during storage and gives good pattern profiles having high aspect ratios even though the resist film is made thick.
    Type: Grant
    Filed: June 3, 1994
    Date of Patent: June 25, 1996
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Tameichi Ochiai, Ryuichiro Takasaki, Yasuhiro Kameyama, Shichiro Takahashi
  • Patent number: 5451495
    Abstract: A recording element having at least one layer comprising a crosslinked polymer having polymeric backbone moieties and crosslinking moieties, the polymeric backbone moieties containing tertiary nitrogen atoms, the crosslinking moieties connecting polymeric backbone moieties at the teritary nitrogen atoms by conversion of the tertiary nitrogen atoms to quaternary amine, the crosslinking moiety having the structure ##STR1## where R' is independently alkyl or aryl and m is an integer of from 1 to 10.
    Type: Grant
    Filed: August 15, 1994
    Date of Patent: September 19, 1995
    Assignee: Eastman Kodak Company
    Inventors: Catherine A. Falkner, John J. Fitzgerald, Dennis J. Savage, Paul D. Yacobucci
  • Patent number: 5391463
    Abstract: Irradiating, with ultraviolet light, surfaces which contain thiol groups, epoxy groups, or vicinal diol groups, results in surfaces which exhibit a reduced adsorption of biomolecules. In the case of surfaces having thiol groups such irradiation also results in a reduced capacity for the bonding of heterobifunctional crosslinking reagents. Such irradiation may be carried out in a patternwise fashion to obtain patterned surfaces.
    Type: Grant
    Filed: April 25, 1991
    Date of Patent: February 21, 1995
    Assignees: The United States of America as represented by the Secretary of the Navy, Geo-Centers, Inc.
    Inventors: Frances S. Ligler, Suresh Bhatia, Lisa C. Shriver-Lake, Jacque Georger, Jeff Calvert, Charles Dulcey
  • Patent number: 5334457
    Abstract: There are disclosed a plastic resin film which comprises a polyester resin composition comprising at least two components of (A) a polyester copolymer and (B) a polymer having conductivity, preferably having a number average molecular weight of 500 to 5000, being laminated on at least one surface of a plastic film support; a light-sensitive photographic material which comprises at least one silver halide emulsion layer being laminated on said film laminate or plastic film; and a method for preparing a plastic film which comprises coating an aqueous solution of the polyester resin composition on at least one surface of a non-oriented plastic film support or uniaxially oriented plastic film support, stretching the coated support to at least monoaxial direction and then completing orientation crystallization.
    Type: Grant
    Filed: September 10, 1991
    Date of Patent: August 2, 1994
    Assignee: Konica Corporation
    Inventors: Yoshihiro Wada, Tohru Kobayashi, Noriki Tachibana
  • Patent number: 5290663
    Abstract: A photopolymer useful in preparing water-developable, solid printing plates is prepared by (A) preparing a urethane prepolymer by reacting a polyoxyalkylene diol (optionally carboxylic acid grafted) with an excess of diisocyanate, followed by chain extending the resulting prepolymer mixture with a dialkylolpropionic acid and preferably with additional diols(s) such as alkane diol(s) and (meth)acrylate-containing diol(s). Use of a new (meth)acrylate-containing diol in such chain extension completes the formation of photopolymer. However, in a third operation (B) hydroxyalkylmethacrylate may be reacted with the result of (A) whether or not (meth)acrylate-containing diol is used in (A). The carboxylic acid groups of the photopolymer may also be partially neutralized with a base. The photopolymer is suitably formulated with additional photoactive (meth)acrylate monomers or oligomers and photoinitiator for casting on a substrate or extruding to form a flexographic printing plate.
    Type: Grant
    Filed: March 1, 1991
    Date of Patent: March 1, 1994
    Assignee: W. R. Grace & Co.-Conn.
    Inventor: Truc-Chi T. Huynh-Tran
  • Patent number: 5286600
    Abstract: A negative photosensitive composition comprising (a-1) a compound having at least two organic groups of the following formula (I):--OCH.sub.2 OR.sup.1 (I)wherein R.sup.1 is an alkyl group, in its molecule and an alkali-soluble resin, or (a-2) an alkali-soluble resin having at least two organic groups of the above formula (I) in its molecule, and (b) a photo-acid-generating material.
    Type: Grant
    Filed: August 10, 1992
    Date of Patent: February 15, 1994
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Tameichi Ochiai, Noriaki Takahashi, Yasuhiro Kameyama
  • Patent number: 5250409
    Abstract: A silver halide photographic material which comprises a support having thereon one or more constituent layers including at least one silver halide emulsion layer, wherein at least one of said constituent layers is a layer formed by (a) coating a composition which contains a high molecular weight compound having at least one repeating unit represented by the following formula (I), and then (b) making the composition undergo a crosslinking reaction: ##STR1## wherein R.sub.1 represents a hydrogen atom, an alkyl group, a chlorine atom, or a cyano group; R.sub.2 and R.sub.3, which may be the same or different, each represents an alkyl group; L.sub.1 and L.sub.2 each represents a divalent linking group; Y represents --O--, or ##STR2## wherein R.sub.4 represents a hydrogen atom, or an alkyl group; X represents a crosslinking group containing an activated vinyl component; and Z represents a counter ion for balancing the electric charge.
    Type: Grant
    Filed: August 27, 1992
    Date of Patent: October 5, 1993
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Shoichiro Yasunami, Yasuo Mukunoki
  • Patent number: 5240808
    Abstract: A light-sensitive composition which comprises at least one polymeric compound having both photocross-linkable groups and functional groups carrying P--OH bonds. The light-sensitive composition can effectively be employed for making lithographic printing plates, IC circuits and photomasks. The light-sensitive composition shows excellent practically acceptable developability with either of an aqueous alkali developer and an aqueous alkaline solution containing or free of organic substances such as organic solvents and/or surfacants. Moreover, when it is used to form PS plates, the resulting lithographic printing plates never cause background contamination and can provide a large number of good printed matters. The composition makes it possible to develop negative working PS plates with developers for positive working PS plates. Therefore, when both positive and negative working PS plates are processed, the use of the composition can save various troubles.
    Type: Grant
    Filed: January 8, 1992
    Date of Patent: August 31, 1993
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Keitaro Aoshima, Masanori Imai
  • Patent number: 5238781
    Abstract: Photosensitive compositions comprisinga) at least one solid film-forming polyphenol,b) at least one compound of formula I ##STR1## wherein n is 2, 3 or 4, Ar is an n-valent benzene or naphthalene radical or a divalent radical of formula II ##STR2## Q is a direct bond, --O--, --SO--, --SO.sub.2 --, --CH.sub.2 --, --C(CH.sub.3)(phenyl)- or --C(CH.sub.3).sub.2 --, each of R.sub.1 and R.sub.2, independently of the other, is C.sub.1 -C.sub.8 alkyl, or phenyl or naphthyl each of which is unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl, or R.sub.1 and R.sub.2 together are 1,2-phenylene or --[C(R')(R")].sub.m --, each of R' and R", independently of the other, is hydrogen, C.sub.1 -C.sub.4 alkyl or phenyl and m is 2, 3 or 4, andc) at least one compound that forms an acid under actinic radiation are described.Those compositions are used as negative resists, especially for producing printing plates, printed circuits and integrated circuits.
    Type: Grant
    Filed: February 27, 1992
    Date of Patent: August 24, 1993
    Assignee: Ciba-Geigy Corporation
    Inventor: Ulrich Schadeli
  • Patent number: 5229252
    Abstract: A photoimageable composition for forming a solder mask has a photopolymerizable acrylate chemical system which renders exposed portions insolvable to alkaline aqueous developers and an epoxy chemical system which hardens the composition after exposure and development. The acrylate chemical system comprises acrylate monomers, epoxy-acrylate oligomers and a photoinitiator. The epoxy chemical system comprises an epoxy resin and a curative therefore. The composition further comprises a cross-linking agent which is reactive with hydroxyl groups of the acrylate and epoxy chemical systems.
    Type: Grant
    Filed: October 21, 1991
    Date of Patent: July 20, 1993
    Assignee: Morton International, Inc.
    Inventors: Kathy M. Flynn, Vinai M. Tara, Kathleen L. Nelson
  • Patent number: 5057397
    Abstract: An electron beam-curable resist composition suitable for fine patterning works in the manufacturing process of semiconductor devices is proposed which is outstandingly stable in storage and capable of being developed using an aqueous alkaline developer solution without scums and giving a patterned resist layer with high contrast and orthogonal cross sectional profile of a line pattern. The composition comprises (A) a triazine compound, such as 2-(4-methoxyphenyl)-4,6-bis(trichloromethyl)-1,3,5-triazine, (B) a cresol novolac resin, of which at least 30% by weight of the phenolic moiety is derived from m-cresol, and (C) an alkoxymethylated melamine resin in specified proportions of (B):(C) and (A):[(B)+(C)]. The sensitivity of the resist composition is greatly enhanced by a heat treatment of the resist layer at 90.degree.-140.degree. C. after patternwise irradiation with electron beams.
    Type: Grant
    Filed: November 16, 1989
    Date of Patent: October 15, 1991
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Masanori Miyabe, Hidekatsu Kohara, Toshimasa Nakayama
  • Patent number: 4980268
    Abstract: The invention relates to negative photoresists of the polyimide type essentially containing, in an organic solvent, in each case at least(a) one polyamide-acid or polyamide-acid derivative prepolymer which can be converted into a highly heat-resistant polyimide polymer,(b) a photoinitiator, and, if appropriate, further customary additives which contain, as the photoinitiator, a compound of the formula IR.sup.1 --SO.sub.2 --SO.sub.2 --R.sup.2 Iin which R.sup.1 and R.sup.2 are as defined.
    Type: Grant
    Filed: March 9, 1989
    Date of Patent: December 25, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Ekkehard Bartmann, Rudolf Klug, Reinhard Schulz, Hartmut Hartner
  • 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: 4902604
    Abstract: Photopolymerizable initiator compositions having high photosensitivity to light sources giving visible rays and the other rays in the longer wavelengths. The compositions containing polymerizable compounds having ethylenic unsaturated bonds and salts formed by an organic boron compound anion and an organic cationic azulene dye compound comprising an azulene ring having a nitrogen atom or a chalcogen atom in the 2- or 4- position can be used for making lithographic printing plates, resinous relief printing plates, and resists or photomasks for printed circuit substrates.The polymerizable compounds having ethylenic unsaturated bonds can be encapsulated to obtain microcapsules to be used for the formation of black-and-white or color images.
    Type: Grant
    Filed: September 30, 1988
    Date of Patent: February 20, 1990
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Jun Yamaguchi, Masaki Okazaki, Takanori Hioki
  • Patent number: 4895880
    Abstract: A process for coating a substrate with an essentially colorless radiation curable composition which comprises coating said substrate with a visible light sensitive composition comprising a free radical addition polymerizable or crosslinkable material and a photobleachable ionic dye-counter ion compound capable of absorbing visible light and generating free radicals; exposing said composition to light to harden said composition; and bleaching said composition to an essentially colorless state, and photohardenable compositions containing photobleachable ionic dye-counter ion compounds as photoinitiators useful in the aforesaid process.
    Type: Grant
    Filed: September 18, 1987
    Date of Patent: January 23, 1990
    Assignee: The Mead Corporation
    Inventors: Peter Gottschalk, Douglas C. Neckers, Gary B. Schuster
  • 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: 4842980
    Abstract: A photohardenable composition comprising 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; and photosensitive materials incorporating the same.
    Type: Grant
    Filed: July 20, 1988
    Date of Patent: June 27, 1989
    Assignee: The Mead Corporation
    Inventors: Peter Gottschalk, Douglas C. Neckers, 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: 4800152
    Abstract: Heat stable, negative resist compositions are provided for use, particularly in deep ultraviolet light X-ray and electron beams. The composition comprises an acid generating onium salt photoinitiator, a source of polyfunctional activated aromatic rings and a source of polyfunctional carbonium ions, with at least one of said sources being a polymer.
    Type: Grant
    Filed: March 16, 1987
    Date of Patent: January 24, 1989
    Assignee: International Business Machines Corporation
    Inventors: Robert D. Allen, Jean M. J. Frechet, Robert J. Twieg, Carlton G. Willson
  • 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: 4772530
    Abstract: A photohardenable composition comprising 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; and photosensitive materials incorporating the same.
    Type: Grant
    Filed: December 18, 1986
    Date of Patent: September 20, 1988
    Assignee: The Mead Corporation
    Inventors: Peter Gottschalk, Douglas C. Neckers, Gary B. Schuster
  • Patent number: 4728594
    Abstract: A photosensitive composition comprising an azide compound represented by the formula: ##STR1## wherein each of X and Y is an aromatic substituent group, at least one of X and Y being an aromatic substituent group having an azide group, and n and m are zeros or integers of 1, and a polymeric compound. Since this composition has high resolution and is photosensitive to light having a wavelength of 436 nm, it permits employment of a reduction projection printer and is suitable for fabrication of semiconductor devices.
    Type: Grant
    Filed: January 14, 1986
    Date of Patent: March 1, 1988
    Assignee: Hitachi Chemical Co., Ltd.
    Inventors: Saburo Nonogaki, Ryotaro Irie, Michiaki Hashimoto, Takao Iwayanagi
  • Patent number: 4701300
    Abstract: Photoresist formulations for forming relief structures from highly heat-resistant polyimide polymers, containing in an organic solvent in essence at least(a) one polyamide ester prepolymer carrying photopolymerizable radicals(b) a radiation-reactive copolymerizable unsaturated compound(c) a photosensitizer(d) a photoinitiator(e) a leuco dye, exhibit enhanced photosensitivity if they contain as the photoinitiator a compound of the type of the N-azidosulphonylarylmaleimides and as leuco dye a compound of the type of the triarylmethanes.
    Type: Grant
    Filed: January 15, 1986
    Date of Patent: October 20, 1987
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Hans J. Merrem, Rudolf Klug, Thomas Herold
  • Patent number: 4677047
    Abstract: Novel compositions of matter which crosslink under the action of light and which contain(A) an aliphatically unsaturated polymerization product which is free of aromatic groups and which can contain structural elements of the formula I ##STR1## (B) a bisimide of the formula II ##STR2## and a sensitizer and, if desired, a further crosslinking agent, where R and R' are alkyl or together are tetramethylene, R.sub.1 is hydrogen, chlorine or methyl, Y and Y' are each --OH or together are --O-- and R.sub.4 is alkylene, arylene or bis-arylene, are suitable, inter alia, for preparing printing plates or as photoresist materials.
    Type: Grant
    Filed: September 23, 1985
    Date of Patent: June 30, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: Joseph Berger, Friedrich Lohse
  • Patent number: 4668608
    Abstract: There are disclosed negative-working resist compositions featuring a binder and a radiation-sensitive compound that loses HX upon exposure, to become less soluble in an aqueous base. X is selected from the group consisting of --CN, halide, and --SO.sub.2 R.sup.1 and R.sup.1 is alkyl of 1-5 carbon atoms or aryl of from 6 to 10 carbon ring atoms.
    Type: Grant
    Filed: September 2, 1986
    Date of Patent: May 26, 1987
    Assignee: Eastman Kodak Company
    Inventor: Michael J. Lindstrom
  • Patent number: 4657842
    Abstract: Photosensitive compositions of matter which are capable of undergoing condensation or addition reactions and may or may not be crosslinkable, and which contain an anthraquinone of the formula I ##STR1## in which X, X', R' and R" are as defined in patent claim 1 and X or X' is, for example, --OH or --NH.sub.2, at least one monomeric, oligomeric or polymeric compound which can be reacted with this anthraquinone, for example, if X is --OH, a polymer with terminal glycidyl groups, and, where relevant, a crosslinking agent and/or a salt of a metal of group Ib or VIII of the periodic table, are suitable for image formation by means of electroless metal deposition.
    Type: Grant
    Filed: November 4, 1985
    Date of Patent: April 14, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: Jurgen Finter, Walter Fischer, Friedrich Lohse
  • Patent number: 4656116
    Abstract: Polyimides of aromatic tetracarboxylic acid derivatives and aromatic diamines where both ortho-positions relative to a phenylene radical bonded to an imide group of the polymer are substituted by alkyl groups can be radiation-crosslinked with organic chromophoric polyazides. Solutions of said polyimides and polyazides in organic solvents can be used as radiation-sensitive coating compositions for, for example, preparing insulating and protective films and in particular for producing printed circuits and integrated circuits.
    Type: Grant
    Filed: October 4, 1984
    Date of Patent: April 7, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: Ottmar Rohde, Josef Pfeifer
  • Patent number: 4615968
    Abstract: Novel compositions of matter which crosslink under the action of light and which contain(A) an aliphatically unsaturated polycondensation product which can contain structural elements of the formula I ##STR1## (B) a bisimide of the formula II ##STR2## and a sensitizer and can, if desired, also contain a further crosslinking agent, where R, R', R.sub.1, Y, Y' and R.sub.4 are as defined in claim 1, are suitable, inter alia, for preparing printing plates or for use as photoresist materials.
    Type: Grant
    Filed: October 26, 1983
    Date of Patent: October 7, 1986
    Assignee: Ciba-Geigy Corporation
    Inventors: Joseph Berger, Friedrich Lohse
  • Patent number: 4614704
    Abstract: A method and composition for increasing the cure depth of a solder mask coating at a low UV energy level. The stable composition, which includes a UV curable compound and a photoinitiator, is characterized by the presence of triphenylphosphite in the composition.
    Type: Grant
    Filed: June 21, 1985
    Date of Patent: September 30, 1986
    Assignee: M&T Chemicals Inc.
    Inventors: Paul L. K. Hung, Mark L. Lavach
  • Patent number: 4601973
    Abstract: A photopolymerizable coating agent made of (a) a low molecular weight epoxy-containing epoxy resin, (b) a high-molecular weight epoxy resin based on aromatic polyols and epichlorohydrin, (c) a light-sensitive ethylenically unsaturated monomer having terminal ethylene groups and (d) a photoinitiator and/or sensitizer, and, if desired, hardeners for epoxy resins. It is used for preparing temporary or permanent protective coatings and photographic relief images.
    Type: Grant
    Filed: January 14, 1985
    Date of Patent: July 22, 1986
    Assignee: Ciba-Geigy Corporation
    Inventor: Sigrid Bauer
  • Patent number: 4587197
    Abstract: A photosensitive polymer composition comprising (A) a poly(amic acid), (B) a compound or a mixture of compounds which can form a compound having two or more amino groups in the molecule, and (C) at least one compound having a boiling point of 150.degree. C. or higher at atmospheric pressure and selected from the group consisting of ##STR1## wherein R.sup.a, R.sup.b, R.sup.c, m and n are as defined in the specification, has good properties and does not produce cracks on a pattern at the time of development obtained from said composition.
    Type: Grant
    Filed: February 8, 1984
    Date of Patent: May 6, 1986
    Assignees: Hitachi, Ltd., Hitachi Chemical Co., Ltd.
    Inventors: Mithumasa Kojima, Fumio Kataoka, Fusaji Shoji, Hitoshi Yokono
  • Patent number: 4578328
    Abstract: There is provided an article of manufacture prepared by(A) applying a coating of a solution containing a polymer having at least one pendant aromatic group and a bis-maleimide to a substrate;(B) allowing the coated substrate to dry;(C) exposing the coated substrate to a source of light for a time sufficient to effect crosslinking of said polymer having at least one pendant organic group and said bis-maleimide; and(D) developing the exposed substrate.
    Type: Grant
    Filed: July 9, 1984
    Date of Patent: March 25, 1986
    Assignee: General Electric Company
    Inventor: William D. Kray
  • Patent number: 4571375
    Abstract: A negative photoresist is formed from a photosensitized ("PS") composition having as an essential component, a homopolymer or copolymer having a major molar amount of a ring-opened unsubstituted tetracyclic norbornene ("NB"), and/or a substituted tetracyclic NB having non-polar substituents, and a minor amount, if any, of another NB, optionally also similarly substituted with non-polar substitutents. The negative photoresist formed by exposure of a film about 1 micron thick of the PS composition to ultraviolet light in the range from about 220-450 nanometers forms, in the contact mode, a pattern of lines and spaces which are developed in a substantially aliphatic hydrocarbon solvent so as to provide a high resolution in the range from about 1 micron to about 2 microns in the pattern. Lines in the pattern have essentially vertical walls and substantially unswollen contours.
    Type: Grant
    Filed: May 24, 1984
    Date of Patent: February 18, 1986
    Inventor: George M. Benedikt
  • Patent number: 4569897
    Abstract: This invention relates to negative photoresist compositions containing thermally stable polyglutarimide polymers dissolved in suitable solvents. The negative resists are useful for producing high resolution images on surfaces by exposing the resist to a wide range of exposing radiation wavelengths and by subsequently developing the unexposed resist with an organic solvent or an aqueous base developer. The polyglutarimide polymers can be formulated so that they are partially soluble in an aqueous base, compatible with aqueous base soluble photosensitizers, and developable in aqueous base solutions, thereby eliminating the need for the use of any organic solvent.
    Type: Grant
    Filed: January 16, 1984
    Date of Patent: February 11, 1986
    Assignee: Rohm and Haas Company
    Inventor: Palaiyur S. Kalyanaraman
  • Patent number: 4565768
    Abstract: A photosensitive composition comprising an equimolar condensation product of an aromatic azide compound having an aldehyde group and isophorone, and an alkali-soluble polymeric compound is a negative-type photoresist with a high resolution suitable for the fabrication of semiconductor devices.
    Type: Grant
    Filed: May 31, 1984
    Date of Patent: January 21, 1986
    Assignee: Hitachi Chemical Company, Ltd.
    Inventors: Saburo Nonogaki, Michiaki Hashimoto
  • Patent number: 4565767
    Abstract: A light-sensitive polymer composition comprising a poly(amic acid), a special bisazide compound and an amine compound can give a film which has high sensitivity and in which portions exposed to light are not easily released by a developing solution at the time of development.
    Type: Grant
    Filed: April 24, 1984
    Date of Patent: January 21, 1986
    Assignees: Hitachi, Ltd, Hitachi Chemical Company, Ltd.
    Inventors: Fumio Kataoka, Fusaji Shoji, Isao Obara, Issei Takemoto, Hitoshi Yokono, Tokio Isogai, Mitsumasa Kojima
  • Patent number: 4565771
    Abstract: Gravure printing plates comprising a plastic printing layer applied on a printing plate base are produced by a method wherein a solid photosensitive layer (L) firmly bonded on the printing plate base is exposed imagewise to actinic light, and the exposed layer is washed out with a developer and then subjected to thermal hardening to form the plastic printing layer. In this process, the photosensitive layer (L) employed contains, as the photosensitive component, a compound possessing two or more aromatic and/or heteroaromatic o-nitrocarbinol ester groups, and a compound which effects crosslinking and possesses two or more reactive groups which are capable of reacting with --COOH groups under the action of heat to form a covalent chemical bond.
    Type: Grant
    Filed: August 22, 1983
    Date of Patent: January 21, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: John Lynch, Reinhold J. Leyrer, Dietrich Saenger
  • Patent number: 4556625
    Abstract: The present invention discloses a method of photolytically developing a colored image on a cellulosic material. In this method, the material is contacted with a nitrogen containing polymer in solution and a mono-sulfonyl azide compound in solution. The sample is thereafter exposed to a UV-containing light source for an amount of time sufficient to develop a color thereon.
    Type: Grant
    Filed: November 25, 1983
    Date of Patent: December 3, 1985
    Assignee: Armstrong World Industries, Inc.
    Inventors: Ronald S. Lenox, Anne L. Schwartz, Charles E. Hoyle
  • Patent number: 4554237
    Abstract: Disclosed are photosensitive resin composition useful for formation of fine patterns on semiconductor devices, magnetic bubble devices, etc. which is highly sensitive and is excellent in developability and which has no problem such as precipitation of azide compounds and remaining azide particles after development and a method for forming fine patterns with said composition.Said photosensitive resin composition comprises (a) at least one polymer compound selected from the group consisting of a novolak resin and a polyhydroxystyrene resin and (b) an azide compound represented by the general formula (1): ##STR1## [wherein X is --N.sub.3 or --SO.sub.2 N.sub.3, Y is ##STR2## R.sup.1 is a lower alkylene such as --CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 --, or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 CH.sub.2 --, a hydroxyalkylene or an aminoalkylene such as ##STR3## (wherein R.sup.4 and R.sup.5 are lower alkyl or hydrogen, R.sup.6 -R.sup.8 are lower alkyl groups, R.sup.
    Type: Grant
    Filed: December 22, 1982
    Date of Patent: November 19, 1985
    Assignees: Hitach, Ltd., Hitachi Chemical Company, Ltd.
    Inventors: Fumio Kataoka, Fusaji Shoji, Hitoshi Yokono, Daisuke Makino, Shigeru Koibuchi, Asao Isobe
  • Patent number: 4511645
    Abstract: A presensitized printing plate which has a photopolymerizing composition layer provided on at least one side of a support, with the photopolymerizing composition being constituted with (A) a polymer containing in its side chains groups represented by the following general formula (I) and carboxylic groups: ##STR1## (wherein R.sub.1 to R.sub.5 each represents a hydrogen atom, a halogeno group, a carboxyl group, a sulfo group, a nitro group, a cyano group, and amido group, an amino group, or an unsubstituted or a substituted alkyl, aryl, alkoxy, aryloxy, alkylamino, arylamino, alkylsulfonyl or arylsulfonyl group; and Z represents an oxygen atom, a sulfur atom, --NH-- or --NR-- (R=alkyl)), (B) a monomer or an olygomer having at least two polymerizable ethylenically unsaturated double bonds, and (C) a photopolymerization initiator.
    Type: Grant
    Filed: September 9, 1983
    Date of Patent: April 16, 1985
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Mitsuru Koike, Kesanao Kobayashi, Tadao Toyama, Hiroshi Misu, Koji Tamoto, Masayuki Iwasaki
  • Patent number: 4503140
    Abstract: Radiation-sensitive polymeric compositions containing metal-carbonyl complexes and the cured insoluble crosslinked resin produced therefrom are disclosed. When coated as a layer on a substrate, the composition is useful as an element in the graphic arts.
    Type: Grant
    Filed: May 18, 1982
    Date of Patent: March 5, 1985
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Robin E. Wright
  • Patent number: 4481281
    Abstract: A polymer composition comprising a urethane having terminal unsaturation and a terminal carboxyl group and which is capable of further free radical polymerization has been synthesized. This polymer can be a liquid or a solid depending on the molecular weight and backbone of the polymer. This polymer as a liquid has been found to be very useful in producing printed circuit boards by photo resist processes.
    Type: Grant
    Filed: September 29, 1982
    Date of Patent: November 6, 1984
    Assignee: W. R. Grace & Co.
    Inventors: Jung-Hsien Tsao, Paul R. Hein
  • Patent number: 4469778
    Abstract: Disclosed is a pattern formation method comprising exposing a photosensitive composition comprising a bisazide compound represented by the following general formula: ##STR1## wherein A stands for an atom or atomic group selected from O, S, CH.sub.2, CH.sub.2 CH.sub.2, SO.sub.2 and S.sub.2, X stands for an atom or atomic group selected from H and N.sub.3, and when X is H, Z is a group of N.sub.3 and when X is N.sub.3, Z is an atom of H or Cl, and a polymeric compound to deep UV rays, to form fine patterns.
    Type: Grant
    Filed: April 14, 1983
    Date of Patent: September 4, 1984
    Assignee: Hitachi, Ltd.
    Inventors: Takao Iwayanagi, Takahiro Kohashi, Saburo Nonogaki, Yoshio Hatano
  • Patent number: 4465768
    Abstract: A radiation-sensitive composition comprising an iodine-containing azide compound at least a part of which can be fixed substantially in a polymer by exposure to a radiation and a polymer, or a radiation-sensitive composition comprising an azide compound, an iodine compound at least a part of which can be fixed substantially in a polymer by exposure to a radiation and a polymer. This composition can be subjected to the dry development with oxygen plasma after the exposure followed by heating.
    Type: Grant
    Filed: July 13, 1982
    Date of Patent: August 14, 1984
    Assignee: Hitachi, Ltd.
    Inventors: Takumi Ueno, Hiroshi Shiraishi, Takao Iwayanagi, Takahiro Kohashi, Saburo Nonogaki
  • Patent number: 4459414
    Abstract: Novel tetrasubstituted phthalic acid derivatives of the formula ##STR1## are described, in which Y.sub.1 and Y.sub.2 are oxygen and Y is ##STR2## or --O--, or one of Y.sub.1 and Y.sub.2 is oxygen and the other is .dbd.N--R" and Y is --O--, and m, n, X, R, R' and R" are as defined in claim 1. The compounds (I) are suitable as sensitizers for photocrosslinkable polymers or as initiators for the photopolymerization of ethylenically unsaturated compounds or for the photochemical crosslinking of polyolefins.
    Type: Grant
    Filed: March 29, 1982
    Date of Patent: July 10, 1984
    Assignee: Ciba-Geigy Corporation
    Inventors: Walter Fischer, Hans Zweifel
  • Patent number: 4427760
    Abstract: A photohardenable material is disclosed. The material is comprised of a copolymer (I') having ethylenically unsaturated bonds and having an acid value of about 5 to 180 and a molecular weight of about 1,500 to 100,000. The copolymer (I') is obtained by reacting carboxyl groups with a copolymer represented by the structural formula (I), as defined within the application. The material is further comprised of a copolymer (II) having a molecular weight of about 50,000 to 500,000. The copolymer (II) is comprised of three monomers whose structural formula is also defined within the application. The material is further comprised of a cross-linking agent having two or more ethylenically unsaturated bonds and a photoactivator. The copolymers (I') and (II) are present in a ratio of about 0.5 to 20.
    Type: Grant
    Filed: June 10, 1982
    Date of Patent: January 24, 1984
    Assignee: Somar Manufacturing Co. Ltd.
    Inventors: Kohtaro Nagazawa, Tsutomu Satoh, Kunio Morikubo, Fujio Tanaka, Masaki Okuyama
  • Patent number: 4407927
    Abstract: By adding a compound represented by the following general formulas: ##STR1## to a conventional photoresist composition comprising a cyclized product of conjugated diene homopolymer or copolymer and a photo-crosslinking agent soluble in an organic solvent, an image having a high degree of resolution can be obtained even when a base board having a surface of a high reflectance is used, with a high reproducibility and without being affected by prebaking conditions.
    Type: Grant
    Filed: June 3, 1982
    Date of Patent: October 4, 1983
    Assignee: Japan Synthetic Rubber Co., Ltd.
    Inventors: Yoichi Kamoshida, Toshiaki Yoshihara, Yoshiyuki Harita, Kunihiro Harada
  • Patent number: 4401745
    Abstract: A composition for ultra-fine pattern formation comprising at least one of acrylic and/or vinyl ketone polymers as the major component and an effective amount of an aromatic azide compound and, in another embodiment, further comprising an effective amount of an organic compound having a vinyl group, and a process for ultra-fine pattern formation therewith. In the process, a required area of a film formed from the composition is irradiated with a corpuscular beam or with electromagnetic wave radiation. The aromatic azide compound or a mixture thereof with the aromatic compound having a vinyl group only in the unexposed areas is subjected to a deactivation treatment within the film, and the unexposed areas of the film are removed with a gas plasma to form an ultra-fine pattern. The composition is suitable for use in the ultra-fine pattern formation of a resist for transistors, integrated circuits (IC), large scale integrated circuits (LSI) or the like in the semiconductor industry.
    Type: Grant
    Filed: August 26, 1981
    Date of Patent: August 30, 1983
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hisashi Nakane, Wataru Kanai, Minoru Tsuda