Azide Containing Patents (Class 430/194)
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Patent number: 9988539Abstract: An active-energy-ray-curable composition including active-energy-ray-polymerizable compounds, wherein the active-energy-ray-polymerizable compounds include a monofunctional monomer, a bifunctional monomer, and a trifunctional monomer, and wherein the monofunctional monomer, the bifunctional monomer, and the trifunctional monomer satisfy conditions (1) and (2) below: (1) [number of functional groups derived from the monofunctional monomer]>[number of functional groups derived from the bifunctional monomer]>[number of functional groups derived from the trifunctional monomer]; and (2) a standard deviation of functional group ratios is from 0.003 through 0.030, the functional group ratios being expressed by [number of functional groups derived from N-functional monomer]/([number of functional groups derived from the monofunctional monomer]+[number of functional groups derived from the bifunctional monomer]+[number of functional groups derived from the trifunctional monomer]), the N being mono, bi, or tri.Type: GrantFiled: October 31, 2016Date of Patent: June 5, 2018Assignee: Ricoh Company, Ltd.Inventors: Shun Saito, Mihoko Matsumoto, Masayuki Koyano, Azumi Miyaake, Yuuki Mizutani, Mio Kumai
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Patent number: 9938241Abstract: A series of diazirine compounds of formula (I) having utility as photocrosslinkers are disclosed. Where, A, L, z, Arx and Ry are as defined herein. Also disclosed are the photodefinable compositions containing these compounds.Type: GrantFiled: September 23, 2015Date of Patent: April 10, 2018Assignee: PROMERUS, LLCInventors: Hugh Burgoon, Crystal D. Cyrus, Larry F. Rhodes
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Patent number: 7285363Abstract: A method for crosslinking one or more molecules comprises crosslinking the one or more molecules with a photactivatable crosslinker by one-photon or multi-photon excitation, wherein the crosslinker comprises at least two photoactive groups linked by a bridging moiety, and further wherein the point volume of the activation has at least one dimension of less than about 1 micron. The method is of particular utility for water-soluble molecules, particularly biologically active water-soluble molecules.Type: GrantFiled: November 10, 2003Date of Patent: October 23, 2007Assignee: The University of ConnecticutInventors: Paul J. Campagnola, Amy R. Howell, Jun Wang, Steven L. Goodman
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Patent number: 7198876Abstract: A method for preparation of a lithographic printing plate, which comprises the steps of: imagewise recording on a lithographic printing plate precursor comprising a support having a hydrophilic surface and a thermosensitive layer, the thermosensitive layer comprising at least one of polymer particles and a microcapsule encapsulating an oleophilic compound therein; and rubbing the printing plate precursor by a rubbing member in the presence of a processing liquid to remove the thermosensitive layer of non-image portions.Type: GrantFiled: April 23, 2003Date of Patent: April 3, 2007Assignee: Fuji Photo Film Co., Ltd.Inventor: Toshifumi Inno
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Patent number: 7015256Abstract: A photosensitive composition for forming a dielectric of the present invention comprising inorganic particles, an alkali developable resin and additives, wherein the additives comprise a compound having a quinonediazido group (C1), a compound containing at least two alkyletherified amino groups in the molecule (C2) and a thermal acid generator (C3), or wherein the inorganic particles comprise inorganic superfine particles (A-I) having a mean particle diameter of less than 0.05 ?m and inorganic fine particles (A-II) having a mean particle diameter of not less than 0.05 ?m. The composition can be calcined at low temperatures to form a dielectric layer with high dimensional precision, said layer having a high dielectric constant and a low dielectric loss. Also provided are a dielectric and an electronic part prepared from the composition.Type: GrantFiled: December 26, 2002Date of Patent: March 21, 2006Assignee: JSR CorporationInventors: Nobuyuki Ito, Hideaki Masuko, Satomi Hasegawa, Atsushi Ito, Katsumi Inomata
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Photofinishing processing system and a processing solution supply cartride for the processing system
Publication number: 20020181960Abstract: A cartridge that supplies fresh photographic processing solution or chemistry to a photoprocessing machine and recovers silver from spent processing solution. The cartridge is designed to integrate a solution supply system and a silver recovery system to facilitate the collection of silver from spent processing solution, form a less-regulated spent solution and reduce chemical exposures to operators of photoprocessing systems.Type: ApplicationFiled: June 13, 2002Publication date: December 5, 2002Inventors: Robert B. Call, Jay E. Mathewson, Donna M. Timmons, Richard R. Horn -
Patent number: 6083661Abstract: Photodefineable cyclobutarene compositions are disclosed. These polymer compositions are useful in composites, laminates, membranes, films, adhesives, coatings, and electronic applications such as multichip modules and printed circuit boards. An example of such photodefineable cyclobutarene compositions is a mixture of a photosensitive agent such as 2,6-bis(4-azidobenzylidene)-4-methylcyclohexanone and a cyclobutarene such as oligomeric divinyltetramethyldisiloxane bisbenzocyclobutane.Type: GrantFiled: August 15, 1994Date of Patent: July 4, 2000Assignee: The Dow Chemical CompanyInventors: Frank L. Oaks, Eric S. Moyer, Edward W. Rutter, Jr., Robert F. Harris
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Patent number: 6004705Abstract: A ceramics green sheet which is suitably used for producing sintered ceramics substrates and the like is disclosed. The ceramics green sheet according to the present invention includes a ceramics powder, a photoinitiator, a UV absorber such as photoinitiation inhibitor organic dyes and inorganic powders, and a photosensitive resin composition. The ceramics green sheet according to the present invention has an advantage that via holes and through holes may be very easily formed with high precision, and fine holes may be formed reliably and inexpensively.Type: GrantFiled: July 22, 1996Date of Patent: December 21, 1999Assignee: Toray Industries, Inc.Inventors: Takaki Masaki, Takao Kitagawa, Akiko Yoshimura, Keiji Iwanaga
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Patent number: 5882836Abstract: A photocurable formulation containing a partially polymerized DVS resin formed by heating DVS monomer (1,3-bis(2-bicyclo?4.2.0!octa-1,3,5-trien-3-ylethenyl)-1,1,3,3-tetramethyl disiloxane) in a solvent at an initial concentration of DVS monomer in the solvent of from about 12 to about 32 weight percent. This photocurable formulation may be used as an interlayer dielectric to fabricate thin film multichip modules.Type: GrantFiled: June 5, 1995Date of Patent: March 16, 1999Assignee: The Dow Chemical CompanyInventors: Pamela S. Foster, Ernest L. Ecker, Edward W. Rutter, Jr., Eric S. Moyer
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Patent number: 5866627Abstract: New photosensitive polyamic acid precursors are disclosed which have the formula: ##STR1## where Z is a tetravalent organic radical which contains at least one aromatic ring, Z' is a divalent organic radical which contains at least one aromatic ring, and R* is a photo polymerizable group. Particularly preferred compounds include BPDA-PDA and BPDA-ODA polyamic acid precursors. The precursor compositions within the practice of this invention are i-line, g-line, and i-/g-line active and show good photoresolution. The films formed exhibit excellent self-adhesion and adhesion to glass ceramic and silicon wafer substrates have low internal stress, a very low degree of solvent swelling, high thermal stability, and excellent mechanical properties such as high modulus/tensile strength and high elongation at break.Type: GrantFiled: June 30, 1997Date of Patent: February 2, 1999Assignee: International Business Machines CorporationInventors: George Czornyj, Moonhor Ree, Willi Volksen, Dominic Changwon Yang
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Patent number: 5650261Abstract: A positive-acting photoresist composition which produces crosslinked images and processes for using the photoresist composition are disclosed. The photoresist composition is prepared from a mixture containing a film forming, polymer-containing, acid hardening resin system, an acid or acid generating material (preferably in the form of a thermal acid generator) for crosslinking the acid hardening resin system, and a photobase generating compound. The photoresist composition is applied as a film onto a substrate surface and selectively imagewise exposed through a photomask to actinic radiation. The actinic radiation causes the photobase generator to produce a base in the imagewise exposed portions of the photoresist film. The photochemically generated base neutralizes the acid in the imagewise exposed areas of the photoresist film.Type: GrantFiled: October 27, 1989Date of Patent: July 22, 1997Assignee: Rohm and Haas CompanyInventor: Mark Robert Winkle
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Patent number: 5486447Abstract: Cost-effective, negative resists having high thermal stability based on oligomeric and/or polymeric polybenzoxazole precursors are disclosed. Also disclosed are resist solutions having a high level of storage stability when they contain a photoactive component in the form of a bisazide and when the polybenzoxazole precursors are hydroxypolyamides having the following structure: ##STR1## where R, R*, R.sub.1, R.sub.1 * and R.sub.2 are aromatic groups, R.sub.3 is an aromatic group or a norbornene residue, and wherein n.sub.1, n.sub.2 and n.sub.3, are defined as follows:n.sub.1 =1 to 100, n.sub.2 and n.sub.3 =0 orn.sub.1 and n.sub.2 =1 to 100, n.sub.3 =0 orn.sub.2 =1 to 100, n.sub.1 and n.sub.3 =0 orn.sub.1, n.sub.2 and n.sub.3 =1 to 100 (with R.noteq.R* or R.sub.1 .noteq.R.sub.1 * or both) orn.sub.1 and n.sub.3 =1 to 100, n.sub.2 =0 (with R.noteq.R* or R.sub.1 .noteq.R.sub.1 * or both),on the condition that: n.sub.1 +n.sub.2 +n.sub.3 .gtoreq.3.Type: GrantFiled: October 27, 1994Date of Patent: January 23, 1996Assignee: Siemens AktiengesellschaftInventors: Albert Hammerschmidt, Eberhard Kuhn, Erwin Schmidt
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Patent number: 5446074Abstract: New photosensitive polyamic acid precursors are disclosed which have the formula: ##STR1## where Z is a tetravalent organic radical which contains at least one aromatic ring, Z' is a divalent organic radical which contains at least one aromatic ring, and R* is a photosensitive group. Particularly preferred compounds include BPDA-PDA and BPDA-ODA polyamic acid precursors. The precursor compositions within the practice of this invention are i-line, g-line, and i-/g-line active and show good photoresolution. The films formed exhibit excellent self-adhesion and adhesion to glass ceramic and silicon wafer substrates have low internal stress, a very low degree of solvent swelling, high thermal stability, and excellent mechanical properties such as high modulus/tensile strength and high elongation at break.Type: GrantFiled: December 17, 1993Date of Patent: August 29, 1995Assignee: International Business Machines CorporationInventors: George Czornyj, Moonhor Ree, Willi Volksen, Dominic C. Yang
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Patent number: 5219700Abstract: A photosensitive composition comprising (a) a 1,2-naphthoquinone-2-diazido-4-sulfonic acid ester compound, (b) alkali-soluble resin, (c) a halomethyloxadiazole compound which releases halogen free radicals by irradiation with actinic rays and (a) a dye which interacts withthe decomposition product of said halomethyloxydiazole compound and discolors or develops color. The composition exhibits excellent development latitude, light safety, visible-on-exposure characteristic and printing resistance.Type: GrantFiled: March 24, 1992Date of Patent: June 15, 1993Assignees: Mitsubishi Kasei Corporation, Konica CorporationInventors: Hideyuki Nakai, Kiyoshi Goto, Hiroshi Tomiyasu, Yoshiko Fujita
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Patent number: 5215867Abstract: A resist is formed by sorption of an inorganic-containing gas into an organic material. The development of the resist occurs by exposure to a plasma (e.g., oxygen reactive ion etching) that forms a protective compound (e.g., a metal oxide) selectively in the resist. The selected regions can be defined by patterning radiation of various types, including visible, ultraviolet, electron beam, and ion beam. In an alternate embodiment, the selected regions are defined by an overlying resist, with the gas sorption protecting the underlying layer in a bilevel resist. The protective compound can protect the organic resist layer during etching of an underlying inorganic layer, such as metal, silicide, oxide, nitride, etc.Type: GrantFiled: May 15, 1987Date of Patent: June 1, 1993Assignee: AT&T Bell LaboratoriesInventors: Larry E. Stillwagon, Gary N. Taylor, Thirumalai N. C. Venkatesan, Thomas M. Wolf
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Patent number: 5089372Abstract: A transfer recording medium is disclosed, comprising a light transmitting support having provided thereon a heat transfer solid ink layer via an interlayer having a photolyzable compound. The recording medium provides a clear and high-quality color image on an image-receiving sheet at high speed and low cost irrespective of surface smoothness of the image-receiving sheet.Type: GrantFiled: November 20, 1989Date of Patent: February 18, 1992Assignees: Tomoegawa Paper Co., Ltd., Matsushita Electric Industrial Co., Ltd.Inventors: Yoshihiro Kirihata, Chikara Murata, Masahide Tsukamoto, Yutaka Nishimura
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Patent number: 5049477Abstract: 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: GrantFiled: April 14, 1989Date of Patent: September 17, 1991Assignee: Fuji Photo Film Co., Ltd.Inventors: Koki Nakamura, Masayoshi Tsuboi, Keizo Koya
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Patent number: 5041570Abstract: A photosensitive agent comprising an aromatic diazide compound represented by Formula (I) ##STR1## wherein X denotes ##STR2## Y denotes --CH.dbd.CH--, ##STR3## R.sub.1 is --CH.sub.2 CH.sub.2 --, R.sub.2 --CH.sub.2 CH.sub.3, R.sub.3 is hydrogen, m is 1, and n is 1,R.sub.6, R.sub.7, R.sub.8, R.sub.9, and R.sub.10 are individually hydrogen, alkyl, substituted alkyl, aryl, or two of R.sub.6 to R.sub.9 form alkylene groups, provided that R.sub.6 to R.sub.9 are not all hydrogen simultaneouslyand use of the photosensitive agent in a photosensitive composition and in a method forming forming an image.Type: GrantFiled: July 31, 1989Date of Patent: August 20, 1991Assignee: Toyo Gosei Kogyo Co., Ltd.Inventors: Noriaki Tochizawa, Hideo Kikuchi
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Patent number: 4963470Abstract: Titanocenes with silylated .pi.-cyclopentadienyl ligands in which one or two carbo- or heterocyclic aromatic rings are bonded to the titanium, the aromatic rings being substituted by fluorine, --CF.sub.3, --C.sub.2 F.sub.5, --CF.sub.2 CL or --CF.sub.2 CH.sub.3 in at least one of the two ortho-positions relative to the metal-carbon bonds, are suitable as photoinitiators for the photopolymerization of ethylenically unsaturated substrates. They are distinguished by a high sensitivity, stability to air and the action of heat, and a high activity in the region of UV light to visible light. They are furthermore readily soluble in the photopolymerizable compositions.Type: GrantFiled: January 19, 1990Date of Patent: October 16, 1990Assignee: Ciba-Geigy CorporationInventors: Bernd Klingert, Franciszek Sitek, Manfred Rembold
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Patent number: 4857428Abstract: A photoresist film containing a phosphate of a formalin condensate of diazodiphenylamine, 2.5-bis (4'-azide-2'- sulphobenzilidene) cyclopentanone Na, polyvinylalcohol, and polyvinylpyrrolidone is formed on the inner surface of a faceplate. The photoresist film is hardened by light exposure using a point or linear light source, which is essentially a circular light source, via a shadow mask having a large number of apertures. A light absorbing film is formed on this photoresist film. Then the hardened photoresist film and the light absorbing film on top of it are removed using a peeling agent.Type: GrantFiled: January 14, 1988Date of Patent: August 15, 1989Assignee: Kabushiki Kaisha ToshibaInventor: Norio Koike
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Patent number: 4849320Abstract: The invention provides a process for the production of an image which comprises(i) applying to a substrate a layer of a liquid composition comprising(A) a cationically polymerizable residue(B) a radiation-activated polymerization initator for (A)(C) a radiation-curable residue that is different from (A) and optionally(D) a radiation activated initiator for the cure of (C),(ii) subjecting the composition to actinic radiation having a wavelength at which initiator (B) is activated but at which the residue (C) and/or initiator (D) is not substantially activated, followed by heating, if necessary, so that (A) is polymerized and the layer of liquid composition is solidified, but remains curable,(iii) subjecting the solidified layer in a predetermined pattern to actinic radiation having a wavelength that is different from that of the radiation used in stage (ii) and at which the radiation-curable residue (C) and/or the initiator (D) is activated, such that in the exposed areas (C) is substantially cured, and(iv) reType: GrantFiled: April 30, 1987Date of Patent: July 18, 1989Assignee: Ciba-Geigy CorporationInventors: Edward Irving, Christopher P. Banks
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Patent number: 4842984Abstract: A novel photosensitive resin composition, which has fairly high sensitivity to light and developable with water comprising of essential components a resin represented by the general formula (I), ##STR1## wherein X, which may be present or absent, represents acetic acid when present, Y stands for a group containing carbon-carbon double bond(s) represented by the formula (II), ##STR2## n is an integer of 10 or greater, more than 0 and less than 1, and t is 0 or 1, and a sodium or potassium salt of 4,4'-diazidostilbene-2,2'-disulfonic acid represented by the general formula (IV), ##STR3## wherein z stands for sodium atom or potassium atom; or the resin represented by the general formula (I), the sodium or potassium salt of 4,4'-diazidostilbene-2,2'-disulfonic acid represented by the general formula (IV), and an aromatic ketone represented by the general formula (V), ##STR4## wherein G stands for hydrogen atom or an amino group or dialkylamino group represented by the general formula (VI), ##STR5## where u is 0,Type: GrantFiled: June 29, 1987Date of Patent: June 27, 1989Assignee: Nitto Boseki Co., Ltd.Inventors: Hajime Serizawa, Koichi Ojima, Kiyoshi Shimizu
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Patent number: 4840869Abstract: Light sensitive compositions are disclosed which comprise 2-halomethyl-1,3,4,-oxadiazole compounds having a heterocyclic radical in the fifth position containing at least one element selected from the group consisting of oxygen, nitrogen, sulphur, and selenium directly or through a vinyl radical.Type: GrantFiled: August 10, 1987Date of Patent: June 20, 1989Assignee: Konishiroku Photo Industry Co., Ltd.Inventors: Noriyasu Kita, Kiyoshi Goto
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Patent number: 4835089Abstract: A thick polymer film containing an aromatic bisazide and/or an aromatic sulfonyl azide compound is formed on a substrate having topography level on its surface to flatten said surface and then heated or the whole surface thereof is exposed to a light. A mask pattern having a dry etching resistance higher than that of the polymer is formed on the polymer film, exposed parts of the polymer film are removed by the dry etching and the exposed parts of the film to be processed are removed to form a pattern.Type: GrantFiled: June 10, 1987Date of Patent: May 30, 1989Assignee: Hitachi, Ltd.Inventors: Takao Iwayanagi, Norio Hasegawa, Toshihiko Tanaka, Hiroshi Shiraishi, Takumi Ueno, Michiaki Hashimoto, Seiichiro Shirai, Kazuya Kadota
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Patent number: 4830953Abstract: Polyimides which contain aliphatic groups can be radiation-crosslinked with chromophoric aromatic polyazides. Solutions in organic solvents can be used as radiation-sensitive coating agents for preparing insulating or protective coatings and as photoresists having high thermal, mechanical and chemical stability.Type: GrantFiled: May 11, 1987Date of Patent: May 16, 1989Assignee: Ciba-Geigy CorporationInventor: John H. Bateman
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Patent number: 4816377Abstract: A high-resolution photosensitive composition which can be plasma-developed, including an acrylic a polymer and a photosensitive compound, of the aromatic azide group, in which the polymer contains, in a side chain, at least one aromatic nucleus where at least one chlorine atom (Cl) has replaced at least one hydrogen atom (H), for example ##STR1##Type: GrantFiled: January 7, 1988Date of Patent: March 28, 1989Assignee: U.S. Philips CorporationInventors: Andre Collet, Serge Gourrier, Olivier Maurin
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Patent number: 4797348Abstract: A dually photosensitive composition useful as a photoresist in the manufacture of ICs and the like electronic devices, which is positively photosensitive by exposure to ultraviolet in a relatively small dose but negatively photosensitive by exposure to ultraviolet in a substantially larger dose than above or by exposure to far ultraviolet light, is obtained by admixing a positive-type photoresist material comprising a novolac resin and an o-naphthoquinone diazide compound with a bisazide compound such as 4,4'-diazidodiphenyl sulfide. The inventive photosensitive composition provides a possibility of developing an ingenious technique for patterning of a photoresist layer on the substrate such as a checkboard-like patterned layer by use of a photomask of a line-and-space pattern.Type: GrantFiled: February 17, 1988Date of Patent: January 10, 1989Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Yoichi Nakamura, Shirushi Yamamoto, Takashi Komine, Akira Yokota, Hisashi Nakane
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Patent number: 4783391Abstract: A radiation-sensitive composition is described, which is comprised of (1) a polymer containing repeating units of the formula: ##STR1## wherein R.sup.1 is a trivalent or tetravalent aromatic or heteroaromatic residue having 6 to 30 carbon atoms, R.sup.2 is a divalent aromatic or heteroaromatic residue having 6 to 30 carbon atoms, R.sup.3 is hydrogen or an ammonium ion, n is 1 or 2, and COOR.sup.3 is located in an ortho or peri position with respect to the amide linkage, (2) an organic compound having a radiation-dimerizable or radiation-polymerizable olefinic double bond and an amino radical or a quaternary ammonium salt, and (3) an aromatic monoazide compound [III] having no substituent or having a neutral or acidic substituent. This composition has a highly improved radiation sensitivity and the sensitive wavelength region of this composition is very broad. This composition can give a highly heat-resistant relief pattern with a good edge sharpness.Type: GrantFiled: November 25, 1986Date of Patent: November 8, 1988Assignee: Toray Industries, Inc.Inventors: Gentaro Ohbayashi, Susumu Umemoto, Hiroo Hiramoto
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Patent number: 4740451Abstract: The invention provides a novel and improved photosensitive or photocurable composition useful as a photoresist material in the manufacturing process of semiconductor devices such as LSIs by the lithographic process involving etching, in particular, with low temperature plasma in a dry process. The photoresist layer formed of the inventive composition is highly resistant against damages even by direct contacting with a photomask used in the pattern-wise exposure of the photoresist to light owing to the improved pliability thereof and good adhesion to the substrate surface in addition to the stability against the attack by the plasma. The composition comprises (a) a phenolic polymer, e.g. a novolac resin or a polymer of a hydroxystyrene, (b) an aromatic azide compound and (c) a polymer of a vinyl alkyl ether, the amounts of the compounds (b) and (c) being limited relative to the amount of the component (a).Type: GrantFiled: May 26, 1987Date of Patent: April 26, 1988Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventor: Hidekatsu Kohara
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Patent number: 4737438Abstract: The negative-working photosensitive composition of the invention, which is suitable as a photoresist material in the photolithographic processing of semiconductor devices, comprises (a) a condensation product of a hydroxy-substituted diphenylamine compound such as 4-hydroxy diphenylamine and a methylol melamine or alkoxylated methylol melamine by the reaction in a medium of phosphoric or sulfuric acid and (b) an azide compound capable of strongly absorbing UV or far UV light. The composition gives a photoresist layer having high resistance against heat in the post-baking and the attack of gas plasma encountered in the dry etching for semiconductor processing.Type: GrantFiled: October 21, 1986Date of Patent: April 12, 1988Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Naoki Ito, Koichiro Hashimoto, Wataru Ishii, Hisashi Nakane
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Patent number: 4728594Abstract: 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: GrantFiled: January 14, 1986Date of Patent: March 1, 1988Assignee: Hitachi Chemical Co., Ltd.Inventors: Saburo Nonogaki, Ryotaro Irie, Michiaki Hashimoto, Takao Iwayanagi
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Patent number: 4640885Abstract: 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: GrantFiled: June 28, 1985Date of Patent: February 3, 1987Assignee: Armstrong World Industries, Inc.Inventors: Ronald S. Lenox, Anne L. Schwartz, Charles E. Hoyle
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Patent number: 4614706Abstract: A film of a photoresist having phenolic hydroxyl groups is irradiated with far-ultraviolet radiation, and is thereafter developed with an alkaline aqueous solution. Using as a mask a resist pattern thus obtained, dry etching is carried out to form a microscopic pattern. Since the photoresist is highly immune against the dry etching, the microscopic pattern can be formed at a high precision. By adding an azide of a specified structure, the photoresist has its sensitivity to the far-ultraviolet radiation enhanced more.Type: GrantFiled: May 2, 1984Date of Patent: September 30, 1986Assignee: Hitachi, Ltd.Inventors: Toshiharu Matsuzawa, Takao Iwayanagi, Kikuo Douta, Hiroshi Yanazawa, Takahiro Kohashi, Saburo Nonogaki
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Patent number: 4588669Abstract: A photosensitive lithographic plate comprising a hydrophilic substrate, a photosensitive diazo resin layer superposed on the substrate, and a layer of a photosensitive polyvinyl acetal resin containing an aromatic azide group in a side chain thereof and having an acid number of 10 to 100 and superposed on the diazo resin layer, and a method for the manufacture of this photosensitive lithographic plate.Type: GrantFiled: May 9, 1984Date of Patent: May 13, 1986Assignee: Fuji Chemicals Industrial Co., Ltd.Inventor: Takateru Asano
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Patent number: 4587197Abstract: 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: GrantFiled: February 8, 1984Date of Patent: May 6, 1986Assignees: Hitachi, Ltd., Hitachi Chemical Co., Ltd.Inventors: Mithumasa Kojima, Fumio Kataoka, Fusaji Shoji, Hitoshi Yokono
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Patent number: 4571375Abstract: 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: GrantFiled: May 24, 1984Date of Patent: February 18, 1986Inventor: George M. Benedikt
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Patent number: 4569897Abstract: 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: GrantFiled: January 16, 1984Date of Patent: February 11, 1986Assignee: Rohm and Haas CompanyInventor: Palaiyur S. Kalyanaraman
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Patent number: 4565768Abstract: 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: GrantFiled: May 31, 1984Date of Patent: January 21, 1986Assignee: Hitachi Chemical Company, Ltd.Inventors: Saburo Nonogaki, Michiaki Hashimoto
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Patent number: 4556625Abstract: 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: GrantFiled: November 25, 1983Date of Patent: December 3, 1985Assignee: Armstrong World Industries, Inc.Inventors: Ronald S. Lenox, Anne L. Schwartz, Charles E. Hoyle
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Patent number: 4554237Abstract: 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: GrantFiled: December 22, 1982Date of Patent: November 19, 1985Assignees: Hitach, Ltd., Hitachi Chemical Company, Ltd.Inventors: Fumio Kataoka, Fusaji Shoji, Hitoshi Yokono, Daisuke Makino, Shigeru Koibuchi, Asao Isobe
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Patent number: 4536421Abstract: A negative photoresist having benzene rings is irradiated with short-wavelength ultraviolet radiation, and is developed to form a photoresist pattern whose sectional shape is an inverted trapezoid. Using the photoresist pattern, the lift-off process having heretofore required troublesome steps can be performed very easily.Type: GrantFiled: July 30, 1981Date of Patent: August 20, 1985Assignee: Hitachi, Ltd.Inventors: Toshiharu Matsuzawa, Kikuo Douta, Takao Iwayanagi, Hiroshi Yanazawa
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Patent number: 4526854Abstract: A method for forming a pattern of a non-light-emitting black material on the inner surface of a faceplate of a color cathode ray tube is provided, which comprises the steps of forming a photoresist layer of a photoresist containing a water-soluble bisazidocompound, a water-soluble diazocompound, and a water-soluble polymeric material, on an inner surface of a faceplate of a color cathode ray tube, selectively exposing parts of the photoresist layer using a shadow mask so as to photocure the exposed parts, developing the photoresist layer to remove unexposed parts of the photoresist layer, thereby forming dots of the photoresist, forming a film of a non-light-emitting black material on the inner surface of the faceplate including the dots, and removing the dots and the non-light-emitting black material on the dots so as to form holes in the film of the non-light-emitting black material.Type: GrantFiled: February 18, 1983Date of Patent: July 2, 1985Assignee: Tokyo Shibaura Denki Kabushiki KaishaInventors: Shingo Watanabe, Takeo Itou
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Patent number: 4469778Abstract: 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: GrantFiled: April 14, 1983Date of Patent: September 4, 1984Assignee: Hitachi, Ltd.Inventors: Takao Iwayanagi, Takahiro Kohashi, Saburo Nonogaki, Yoshio Hatano
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Patent number: 4391894Abstract: A method for preparing a substantially uniformily dyed photosensitive composition useful in the reprographic arts, and compositions useful therefor. A water soluble basic dye is reacted with an organic acid, or an ammonium or alkali metal salt thereof which is preferably monofunctional and the reaction product is substantially uniformly dissolved in a photosensitive diazo composition to impart the desired dye color thereto. The resultant dye colored photosensitive composition may then be coated upon a suitable support, for example, a film or metal sheet, to provide a photosensitized product useful in the reprographic arts, which possesses substantially uniform color characteristics and extended shelf life.Type: GrantFiled: August 28, 1981Date of Patent: July 5, 1983Assignee: Polychrome CorporationInventors: Ken-ichi Shimazu, Albert Deutsch
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Patent number: 4388397Abstract: A novel photosensitive composition for dry development in the ultra-fine pattern formation of the semiconductor industry, which is composed of at least one of acrylic and vinyl ketone polymers and a specified subliming hisazide compound as a photocuring agent, is disclosed.The use of the photosensitive composition provides a very effective ultra-fine pattern formation process in the semiconductor industry with such advantages that unexposed areas are selectively removable by treating with a plasma, and consequently plasma development becomes available so that high resolution may easily be obtained. Automating and dry processing of all the stages ranging from development processing to stripping processing become available when using the photosensitive composition of this invention. No expensive treating reagents are needed and environmental pollution is eliminated.Type: GrantFiled: March 27, 1981Date of Patent: June 14, 1983Assignee: Tokyo Ohka Kogyo Kabushiki KaishaInventor: Wataru Kanai
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Patent number: 4347300Abstract: This invention relates to novel photosensitized sheet constructions which, upon exposure to an energy source through a screened image, can accurately and simultaneously reproduce said image in both its negative and positive forms.Type: GrantFiled: May 11, 1978Date of Patent: August 31, 1982Assignee: Polychrome CorporationInventors: Ken-Ichi Shimazu, Takao Nakayama
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Patent number: 4324852Abstract: A radiation-sensitive element is disclosed including a radiation-sensitive layer comprised of a cobalt(III)complex and a photoreductant. A process is disclosed in which the photoreductant is converted to a reducing agent by exposure to electromagnetic radiation longer than 300 nanometers. The reducing agent is then reacted with a cobalt(III)complex. Images can be recorded directly within the radiation-sensitive layer or in a separate image-recording element or layer by use of the residual cobalt(III)complex not exposed or one or more of the reaction products produced by exposure. By using the ammonia liberated from ammine ligand containing cobalt(III)complexes on exposure in combination with imagewise and uniform exposures, positive or negative images can be formed in diazo image-recording layers or elements associated with the radiation-sensitive layer.Type: GrantFiled: June 7, 1979Date of Patent: April 13, 1982Assignee: Eastman Kodak CompanyInventors: Anthony Adin, James C. Fleming
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Patent number: 4271251Abstract: A stabilized photosensitive composition comprising a leuco dye, a photooxidizing agent, and further a 2,4-dihydroxybenzaldoxime which is suitable for use in lithography, photoresists, etc., for obtaining visible contrast between the exposed and unexposed areas.Type: GrantFiled: October 19, 1979Date of Patent: June 2, 1981Assignee: Fuji Photo Film Co., Ltd.Inventors: Yoshimasa Aotani, Hiroshi Misu, Akira Nagashima
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Patent number: 4232106Abstract: Photosensitive compositions containing 2-halomethyl-5-vinyl-1,3,4-oxadiazole compounds represented by the following general formula (I): ##STR1## wherein W represents a substituted or unsubstituted aryl group, X represents a hydrogen atom, an alkyl group or an aryl group, Y represents a fluorine atom, a chlorine atom or a bromine atom, and n represents an integer of 1 to 3.Type: GrantFiled: November 16, 1978Date of Patent: November 4, 1980Assignee: Fuji Photo Film Co., Ltd.Inventors: Masayuki Iwasaki, Shigeru Sato, Yasuo Inoue, Akira Nagashima
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Patent number: 4215041Abstract: Substituted amino-benzene diazonium compounds particularly useful for the preparation of lithographic printing plates, a process for the preparation of this compound and printing plate, and for the use of the plate; and a lithographic plate presensitized with this compound, are described.Type: GrantFiled: July 12, 1978Date of Patent: July 29, 1980Assignee: Eastman Kodak CompanyInventors: Georges A. Phlipot, Jacques R. G. Haeck, Simone J. Kempen