And Monomeric Processing Ingredient Patents (Class 430/191)
  • Patent number: 4948697
    Abstract: The invention provides a positive working photosensitive element with improved odor and increased photospeed which comprises coating a formulation containing at least one novolak or polyvinyl phenol resin, at least one o-quinone diazide and a solvent mixture comprising propylene glycol alkyl ether and propylene glycol alkyl ether acetate, onto a substrate, drying, exposing to imaging energy and developing.
    Type: Grant
    Filed: July 5, 1989
    Date of Patent: August 14, 1990
    Assignee: Hoechst Celanese Corporation
    Inventor: Dana Durham
  • Patent number: 4943511
    Abstract: Positive photoresist compositions are provided which contain (a) a mixture of mono-, di-, and triesters of 2,3,4-trihydroxybenzophenone and 1,2-naphthoquinone-2-diazo-4-sulfonic acid and (b) a novolak resin selected from resins prepared from a phenolic component having a high p-cresol content or from a mixture of formaldehyde and an aromatic aldehyde.
    Type: Grant
    Filed: July 6, 1989
    Date of Patent: July 24, 1990
    Assignee: Morton Thiokol, Inc.
    Inventors: Richard M. Lazarus, Edward J. Reardon, Sunit S. Dixit
  • 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: 4933257
    Abstract: Disclosed herein is an antistatic photo-resist containing an antistatic agent. Since antistatic photo-resist according to the present invention is hardly charged, it can be suitably used as a mask in implanting ions into semiconductor substrate.
    Type: Grant
    Filed: September 18, 1989
    Date of Patent: June 12, 1990
    Assignees: Mitsubishi Denki Kabushiki Kaisha, Mitsubishi Chemical Industries Limited
    Inventors: Konoe Miura, Tameichi Ochiai, Yasuhiro Kameyama, Tooru Koyama, Takashi Okabe, Tomoharu Mametani
  • Patent number: 4931381
    Abstract: A process for converting a normally positive working photosensitive composition to a negative working composition. One forms a composition containing an alkali soluble resin, a 1,2 quinone diazide-4-sulfonyl compound and an acid catalyzed crosslinker in a solvent mixture. After drying and imagewise exposing, the composition is baked and developed to produce a negative image.
    Type: Grant
    Filed: November 8, 1988
    Date of Patent: June 5, 1990
    Assignee: Hoechst Celanese Corporation
    Inventors: Mark A. Spak, Donald Mammato, Dana Durham, Sangya Jain
  • Patent number: 4929536
    Abstract: A process for converting a normally positive working photosensitive composition to a negative working composition is disclosed. One forms a composition containing an alkali soluble resin, a 1,2 quinone diazide-4-sulfonyl compound and an acid catalyzed crosslinker in a solvent mixture. After drying and imagewise exposing, the composition is baked and developed to produce a negative image. The image-reversal negative-working photoresists of this invention have superior storage stability and shelf life.
    Type: Grant
    Filed: November 8, 1988
    Date of Patent: May 29, 1990
    Assignee: Hoechst Celanese Corporation
    Inventors: Mark A. Spak, Donald Mammato, Dana Durham, Sangya Jain
  • Patent number: 4929534
    Abstract: A positive-working photosensitive mixture containing an o-quinone diazide and a binder is disclosed wherein the mixture contains a compound which is able to form an azo coupling with the o-quinone diazide. A copying material produced with the photosensitive mixture has a high photosensitivity and an exceptional developer resistance. The photosensitive mixture is used in reproduction technique, and also in the field of resists.
    Type: Grant
    Filed: August 26, 1988
    Date of Patent: May 29, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Trutz-Ulrich Stephani, Dieter Mohr, Britta Maisel, Werner Frass
  • Patent number: 4927732
    Abstract: A positive-working photosensitive composition is disclosed that comprises a photosensitive compound which is either of the o-quinone diazide type or comprises a photolytic acid donor in combination with a compound containing a C--O--C group, a binder which is soluble or swellable in an aqueous-alkaline solution and a dye of the general formula I ##STR1## The photosensitive composition of the present invention has a higher photosensitivity than comparable compositions containing other dyes.
    Type: Grant
    Filed: October 20, 1988
    Date of Patent: May 22, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hans-Joachim Merrem, Gerhard Buhr, Ruediger Lenz
  • Patent number: 4904564
    Abstract: An image is provided by depositing a first layer of a photoresist containing a phenolic-formaldehyde novolak type polymer and an imidazole, benzimidazole, triazole, or indazoles to increase the solubility of the layer in aqueous alkaline developer after exposure to imaging radiation; depositing on the first layer a second layer of a photoresist containing a phenolic-formaldehyde novolak type polymer; the second layer having a lower degree of solubility in aqueous alkaline developer after exposure to imaging radiation; exposing the layers to imaging radiation; and developing the layers.
    Type: Grant
    Filed: June 16, 1988
    Date of Patent: February 27, 1990
    Assignee: International Business Machines Corporation
    Inventor: Kaolin N. Chiong
  • Patent number: 4898803
    Abstract: A light-sensitive composition comprises at least one polyuretane resin having repeating unit represented by formula (I) and/or repeating unit represented by formula (II) and which is insoluble in water and soluble in aqueous alkaline solution; and at least one positive-working light-sensitive compound: ##STR1## wherein R.sub.1 represents a bivalent aliphatic or aromatic hydrocarbon which may have a substituent; R.sub.2 represents hydrogen atom or an alkyl, an aralkyl, an aryl, an alkoxy or an aryloxy group which may be substituted with a substituent; R.sub.3, R.sub.4 and R.sub.5 may be the same or different and independently represent a single bond or a bivalent aliphatic or aromatic hydrocarbon group which may have a substituent and Ar represents a trivalent aromatic hydrocarbon group which may have a substituent.
    Type: Grant
    Filed: November 12, 1987
    Date of Patent: February 6, 1990
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Toshiaki Aoai, Keitaro Aoshima, Akira Nagashima
  • Patent number: 4894311
    Abstract: A positive-working photoresist composition containing an alkali-soluble novolak resin and a photosensitive compound represented by the formula ##STR1## wherein D.sub.1 and D.sub.2, which may be the same or different, each represents a 1,2-naphthoquinonediazido-5-sulfonyl group or a 1,2-naphthoquinonediazido-4-sulfonyl group; R.sub.1 and R.sub.2, which may be the same or different, each represents an alkoxy group, or an alkyl ester group; and a, b, c, and d each is 0 or an integer from 1 to 5, provided that (a+b).gtoreq.1 and (c+d).gtoreq.1.The photoresist composition is excellent in sensitivity and resolving power and forms a resist pattern having good sectional shape and high heat resistance on, for example, a semiconductor. The photoresist composition is also applicable for forming a resist pattern having a line width of less than 1 .mu.m.
    Type: Grant
    Filed: October 29, 1987
    Date of Patent: January 16, 1990
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kazuya Uenishi, Yasumasa Kawabe, Tadayoshi Kokubo
  • Patent number: 4889788
    Abstract: The invention describes a photosensitive composition, a copying material prepared from this composition, and a process for the production of negative relief copies, in which a photosensitive composition or a photosensitive material, respectively, is used, that comprises a support and a photosensitive composition coated onto the suppoort and comprising a photosensitive 1,2-quinonediazide or a photosensitive mixture, a binder that is soluble in aqueous-alkaline solutions and an s-triazine of the general formula I ##STR1## wherein R denotes akyl, allyl, alkoxy, alkoxycarbonyl, alkoxycarbonylakkenyl, each having from 1 to 4 carbon atoms in the alkyl or alkenyl group, aryloxy, halogen or a nitro group andn stands for 1 to 3. The material is exposed imagewise under a negative original, thereafter heated and, after cooling, exposed without an original or optionally under a positive original, then developed by means of an aqueous-alkaline developer and optionally baked.
    Type: Grant
    Filed: July 27, 1988
    Date of Patent: December 26, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Paul Stahlhofen, Hans W. Frass
  • Patent number: 4889789
    Abstract: A photosensitive composition which substantially comprises a binder which is insoluble in water and soluble in aqueous-alkaline solutions, a photosensitive 1,2-naphthoquinone-diazide or a photosensitive mixture comprised of a compound which splits off acid upon exposure to light and a compound containing at least one acid-cleavable C-O-C group, and a thermally crosslinking compound comprising a urea or urethane-formaldehyde condensation product is disclosed. Also disclosed is a copying material prepared from this composition. The material has a good shelf life and can be processed as a positive or negative-working material, and also according to the photocomposing method. For development customary developer solutions are used.
    Type: Grant
    Filed: April 4, 1988
    Date of Patent: December 26, 1989
    Assignee: Hoechst Aktiengsellschaft
    Inventor: Paul Stahlhofen
  • Patent number: 4889787
    Abstract: A positive-acting photosensitive proofing element is constructed with a thermal adhesive layer having a Tg between 45.degree. C. and 60.degree. C., said adhesive comprising a polymer or copolymer derived from an ethylenically unsaturated monomer and 0.5 to 40% by weight of a polyvinyl ether polymer as a flexibilizer.
    Type: Grant
    Filed: April 25, 1988
    Date of Patent: December 26, 1989
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Arlene K. Musser
  • Patent number: 4883739
    Abstract: A light-sensitive resin composition comprising a light-sensitive substance represented by the formula (A) shown below and an alkali-soluble resin: ##STR1## wherein R.sub.1 to R.sub.8 are independently hydrogen, a hydroxyl group, a halogen atom, an alkyl group, an alkoxy group, an aralkyl group, an aryl group, an amino group, a monoalkylamino group, a dialkylamino group, an acylamino group, an alkylcarbamoyl group, an arylcarbamoyl group, an alkylsulfamoyl group, an arylsulfamoyl group, a carboxyl group, a cyano group, a nitro group, an acyl group, an alkyloxycarbonyl group, an aryloxycarbonyl group, an acyloxy group, -OD, or ##STR2## (wherein R is hydrogen, or an alkyl group, and D is a 1,2-naphthoquinonediazido-5-sulfonyl group or a 1,2-naphthoquinonediazido-4-sulfonyl group);R.sub.9 to R.sub.12 are independently hydrogen or a lower alkyl group; andZ is oxygen or a single bond; provided that at least one of R.sub.1 to R.sub.
    Type: Grant
    Filed: September 16, 1988
    Date of Patent: November 28, 1989
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Shinji Sakaguchi, Shiro Tan
  • Patent number: 4882260
    Abstract: The photosensitive composition, which is suitable as a photoresist material in fine patterning works for the manufacture of semiconductor devices, contains, as a photoextinctive agent, a combination of an alkali-insoluble dye and an alkali-soluble dye each having absorptivity of light in the wavelength region from 230 to 500 nm in a specified amount and in a specified ratio between them. By virtue of the formulation of combined dyes, the undesirable phenomenon of halation by the underlying aluminum coating layer on the substrate surface is greatly decreased so that patterned resist layer obtained with the composition is a high-fidelity reproduction of the original pattern even in a submicron range of fineness with good rectangularity of the cross sectional form of the patterned lines.
    Type: Grant
    Filed: June 5, 1987
    Date of Patent: November 21, 1989
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hidekatsu Kohara, Nobuo Tokutake, Masanori Miyabe, Toshimasa Nakayama, Shingo Asaumi, Hatsuyuki Tanaka, Yoshiaki Arai
  • Patent number: 4880722
    Abstract: The dissolution rate in alkaline developer solutions of image-wise exposed photoresist systems based on diazoquinone sensitized polyamic acid is reduced to prepare relief images of fine line resolution by reducing the acidity of the polyamic acid prior to exposure.
    Type: Grant
    Filed: October 8, 1987
    Date of Patent: November 14, 1989
    Assignee: International Business Machines Corporation
    Inventors: Wayne M. Moreau, Kaolin N. Chiong
  • Patent number: 4873176
    Abstract: The invention provides a method for forming a photoresist mask on a substrate resistant to reticulation during plasma etching. The method comprises the steps of forming an imaged and developed photoresist coating over an integrated circuit substrate where the photoresist contains an essentially unreacted acid activated cross linking agent, and subjecting said substrate to an etching plasma in a gaseous stream that contains a Lewis acid. Contact of the surface of the photoresist film with the Lewis acid causes cross linking of the surface of the photoresist film during plasma etching with the formation of a reticulation resistant surface layer.
    Type: Grant
    Filed: August 28, 1987
    Date of Patent: October 10, 1989
    Assignee: Shipley Company Inc.
    Inventor: Thomas A. Fisher
  • Patent number: 4871644
    Abstract: Photoresist compositions which operate positively and contain at least one ocmpound of the formula I ##STR1## in which X is --C.sub.n H.sub.2n --, --O--, --S-- or --C(O)--, n being a number from 1 to 6. These compositions are particularly suitable for use as positively-operating copying lacquers.
    Type: Grant
    Filed: September 22, 1987
    Date of Patent: October 3, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Sigrid Bauer
  • Patent number: 4863827
    Abstract: A process for forming a multi-level positive working photosensitive element. One forms a composition containing an alkali soluble resin, an o-quinonediazide compound and an in-situ generated acid catalyzed crosslinker in a solvent mixture. After coating on a substrate, drying and partially cross-linking the first layer, a second positive working light sensitive layer is applied. Each light sensitive layer is activated by u.v. radiation in different parts of the spectrum. The top layer is imagewise exposed and developed to form a mask. The second layer is flood exposed through this mask and developed. Each development is conducted with an aqueous alkaline solution.
    Type: Grant
    Filed: October 20, 1986
    Date of Patent: September 5, 1989
    Assignee: American Hoechst Corporation
    Inventors: Sangya Jain, Yuh-Loo Chang
  • Patent number: 4863829
    Abstract: A positive type photoresist composition comprising a novolak resin and O-quinone diazide compound, the novolak resin being one which is obtained by the addition condensation reaction of a phenol and formaldehyde which is performed in one stage by using as a catalyst an organic acid salt of a divalent metal which is more electropositive than hydrogen, or in two stages by using an acid catalyst in the subsequent stage, the phenol being at least one compound represented by the formula ##STR1## wherein R is hydrogen or an alkyl group of carbon number 1 to 4, the compound being such that the average carbon number in the substituent per one phenol nucelus is 0.5 to 1.5 and the ones with the substituent at the ortho- or para-position with respect to the hydroxyl group account for less than 50 mol %, is disclosed. The positive type photoresist composition of the invention has an improved resolving power, i.e., .gamma.-value.
    Type: Grant
    Filed: March 29, 1988
    Date of Patent: September 5, 1989
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Akihiro Furuta, Makoto Hanabata, Seimei Yasui, Osamu Hiroaki, Naoyoshi Jinno
  • Patent number: 4863828
    Abstract: A positive-working photoresist composition is disclosed, which comprises a light-sensitive substance of 1,2-naphthoquinonediazide-4- and/or -5-sulfonate of 2,3,4,3',4',5'-hexahydroxybenzophenone and an alkali-soluble novolak resin dissolved in ethyl lactate or methyl lactate.
    Type: Grant
    Filed: January 20, 1988
    Date of Patent: September 5, 1989
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Yasumasa Kawabe, Kazuya Uenishi, Tadayoshi Kokubo
  • Patent number: 4853314
    Abstract: A positive-working radiation-sensitive coating solution is disclosed which contains a radiation-sensitive compound, e.g., a 1,2-naphthoquinone diazide, or a radiation-sensitive combination of compounds, e.g., a compound with at least one C-O-C bond which can be split by acid and a compound which upon radiation forms a strong acid, and at least one organic solvent which comprises a mono-C.sub.1 to C.sub.4 -alkyl ether of 1,2-propanediol. The coating solution is less toxic and results in a better layer leveling than known positive-working photoresist solutions.
    Type: Grant
    Filed: June 10, 1988
    Date of Patent: August 1, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hans Ruckert, Ralf Ohlenmacher
  • Patent number: 4847178
    Abstract: A positive type photosensitive composition capable of improving the drawback in the conventional positive type photosensitive resin composition, improving adhesion between the positive type photoresist and the substrate and improving developability is provided by incorporating benzotriazole carboxylic acids in the positive type photoresist.
    Type: Grant
    Filed: April 30, 1987
    Date of Patent: July 11, 1989
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventor: Hiroshi Komano
  • Patent number: 4845008
    Abstract: A positive-working light-sensitive composition is herein disclosed, which comprises a mixed organic solvent consisting of (i) at least one organic solvent having a boiling point of at least 40.degree. C. and less than 100.degree. C., (ii) at least one organic solvent having a boiling point of at least 100.degree. C. and less than 140.degree. C., and (iii) at least one organic solvent having a boiling point of at least 140.degree. C. and less than 210.degree. C.; or (a) at least one organic solvent as defined in the above item (i), (b) at least one organic solvent as defined in the item (ii), (c) at least one organic solvent having a boiling point of at least 210.degree. C.
    Type: Grant
    Filed: February 11, 1987
    Date of Patent: July 4, 1989
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Akira Nishioka, Toshimi Hirano, Keiji Akiyama
  • Patent number: 4842986
    Abstract: A positively working resist material is disclosed, comprising a compound having at least one silyl ether group and capable of directly dissociating an Si-O-C bond upon irradiation with far ultraviolet rays, X-rays, an electron beam, or an ion beam. The resist material has high sensitivity to high energy radiation, excellent resistance to dry etching, and can be developed with an alkaline aqueous solution.
    Type: Grant
    Filed: July 28, 1986
    Date of Patent: June 27, 1989
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Nobuaki Matsuda, Tadayoshi Kokubo, Toshiaki Aoai, Akira Umehara, Yoshimasa Aotani
  • Patent number: 4840869
    Abstract: 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: Grant
    Filed: August 10, 1987
    Date of Patent: June 20, 1989
    Assignee: Konishiroku Photo Industry Co., Ltd.
    Inventors: Noriyasu Kita, Kiyoshi Goto
  • Patent number: 4837121
    Abstract: A phenolic resin composition comprising units of formula (I): ##STR1## wherein R.sub.1 is a halogen and R.sub.2 is a lower alkyl group having 1 to 4 carbon atoms and said units of formula (I) are made by condensing the corresponding halogen-substituted resorcinol of formula (A): ##STR2## wherein R.sub.1 is defined above, with the corresponding para-lower alkyl-substituted 2,6-bis(hydroxymethyl)-phenol of formula (B): ##STR3## wherein R.sub.2 is defined above, and wherein the mole ratio of A:B is from about 0.5:1 to 1.7:1. This phenolic resin may be mixed with photoactive compounds (e.g. 1,2-naphthoquinone diazide sensitizers ) to prepare a light-sensitive composition useful as a positive-working photoresist.
    Type: Grant
    Filed: November 23, 1987
    Date of Patent: June 6, 1989
    Assignee: Olin Hunt Specialty Products Inc.
    Inventors: Andrew J. Blakeney, Alfred T. Jeffries, III, Thomas R. Sarubbi
  • Patent number: 4828960
    Abstract: A reflection limiting photoresist is disclosed.
    Type: Grant
    Filed: November 13, 1986
    Date of Patent: May 9, 1989
    Assignee: Honeywell Inc.
    Inventor: Craig Hertog
  • Patent number: 4822713
    Abstract: A light-sensitive composition for use in making a light-sensitive layer of, for instance, a presensitized plate from which a lithographic printing plate is to be prepared, which comprises a fluorine-containing surfactant and is characterized in that the fluorine-containing surfactant is a copolymer of (i) an acrylate or methacrylate having a fluoroaliphatic group, Rf, which has 3 to 20 carbon atoms and at least 40% by weight of fluorine atoms and at least three terminal carbon atoms of which are fully fluorinated; and (ii) a poly(oxyalkylene) (meth)acrylate and that Rf group-containing (meth)acrylate monomer unit is present in the copolymer in an amount of from 25 to 70% by weight based on the total weight of the copolymer. The composition provides a light-sensitive layer of a uniform thickness and it provides a lithographic printing plate having acceptable and excellent properties.
    Type: Grant
    Filed: January 21, 1987
    Date of Patent: April 18, 1989
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Akira Nishioka, Masayuki Kamei, Toshihiko Umaba
  • Patent number: 4818658
    Abstract: The subject invention involves reduction of light reflection into a photoresist coating over a reflective substrate by the use of a photoactive compound in a photoresist formulation that is the reaction product of a diazooxide and curcumin.
    Type: Grant
    Filed: April 17, 1987
    Date of Patent: April 4, 1989
    Assignee: Shipley Company Inc.
    Inventors: Robert L. Martin, M. Martha Rajaratnam, Pamela Turci
  • Patent number: 4816375
    Abstract: A photosolubilizable composition contains both a compound capable of producing an acid by irradiation with actinic rays and a compound which has at least one silyl ether or silyl ester group capable of being decomposed by an acid; optionally, a compound having at least one silyl ether group has at least one hydrophilic group, providing for increased solubility in a developing solution under the action of an acid, thus enhancing the photosensitivity and the development latitude of the composition.
    Type: Grant
    Filed: April 30, 1987
    Date of Patent: March 28, 1989
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Toshiaki Aoai
  • Patent number: 4808501
    Abstract: A color filter is formed on a support, such as a charge coupled device, by (a) forming a layer on a support with a composition comprising a positive photoresist and a dye; said dye being soluble in the solvent of said photoresist; (b) exposing predetermined portions of said layer to radiation adapted to increase the solubility of said coating in the exposed areas; (c) developing said exposed areas to form a pattern of filter elements; and (d) repeating said steps with a different color dye in said composition; wherein said dye constitutes in excess of 10% by weight, dry basis of said composition, is substantially non-absorptive in the exposure wavelength of said composition, and provides predetermined absorptive characteristics for the specified filter element and said dye possessing substantially the same polarity as said composition.
    Type: Grant
    Filed: May 15, 1987
    Date of Patent: February 28, 1989
    Assignee: Polaroid Corporation, Patent Dept.
    Inventor: Carl A. Chiulli
  • Patent number: 4801527
    Abstract: A presensitized plate for use in making a planographic printing plate is described, comprising an aluminum plate having an anodized film layer, a hydrophilic layer provided on said anodized film layer and a lithographically suitable light-sensitive layer on said hydrophilic layer, said hydrophilic layer comprising a hydrophilic compound having at least one amino group and at least one group selected from the class consisting of a carboxyl group in the free acid form or salt form, a sulfo group in the free acid form or salt form, and a hydroxyl group has prolonged life on the printing press and at the same time is resistant to scumming on non-image areas.
    Type: Grant
    Filed: April 21, 1987
    Date of Patent: January 31, 1989
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Shuiti Takamiya, Hirokazu Sakaki
  • Patent number: 4801518
    Abstract: A method of forming a photoresist pattern wherein a photoresist coating film of naphthoquinone diazide sulfonate of novolak is formed on a substrate layer, the photoresist coating film is exposed by selectively irradiating with near ultraviolet radiation of 350 to 450 nm through a photomask, and the exposed photoresist coating film is developed with an either a negative type or positive type developing solution. The resultant photoresist pattern is usable for manufacturing a highly integrated circuit such as LSI which requires fine processing techniques.
    Type: Grant
    Filed: December 3, 1987
    Date of Patent: January 31, 1989
    Assignee: Oki Electric Industry, Co., Ltd.
    Inventors: Yoshio Yamashita, Ryuji Kawazu, Toshio Itoh, Takateru Asano, Kenji Kobayashi
  • Patent number: 4797346
    Abstract: A light-sensitive composition for use in the preparation of positive-type light-sensitive lithographic printing plate which comprises an o-naphthoquinone diazide compound and novolak resin in which the novolak resin comprises two different novolak resins each being prepared by the polycondensation or co-polycondensation of an aldehyde with at least one compound selected from the group consisting of phenol, m-cresol, o-cresol and p-cresol.
    Type: Grant
    Filed: May 13, 1987
    Date of Patent: January 10, 1989
    Assignee: Konishiroku Photo Industry Co., Ltd.
    Inventors: Takeshi Yamamoto, Nobumasa Sasa, Miegi Nakano
  • Patent number: 4797348
    Abstract: 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: Grant
    Filed: February 17, 1988
    Date of Patent: January 10, 1989
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Yoichi Nakamura, Shirushi Yamamoto, Takashi Komine, Akira Yokota, Hisashi Nakane
  • Patent number: 4797345
    Abstract: Light-sensitive 1,2-naphthoquinone-2-diazide-4-sulfonic acid monoester of a cycloalkyl-substituted phenol corresponding to the formula: ##STR1## wherein n is from about 2 to about 10 and their use in light-sensitive mixtures (e.g. positive-working photoresist compositions) also containing alkali-soluble resins such as phenol-formaldehyde novolaks and cresol-formaldehyde novolaks as well as substrates coated therewith.
    Type: Grant
    Filed: July 1, 1987
    Date of Patent: January 10, 1989
    Assignee: Olin Hunt Specialty Products, Inc.
    Inventor: Alfred T. Jeffries, III
  • Patent number: 4792516
    Abstract: A photosensitive composition comprising (a) a photosensitive component such as an aromatic diazo compound or an aromatic azide, (b) a polymer and (c) a quaternary alkylammonium salt wherein each straight- or branched-chain alkyl group has 1 to 7 carbon atoms is suitable for producing a positive type or negative type photresist excellent in contrast and sensitivity in the microlithography of semiconductor elements.
    Type: Grant
    Filed: January 5, 1987
    Date of Patent: December 20, 1988
    Assignee: Hitachi Chemical Company
    Inventors: Minoru Toriumi, Hiroshi Shiraishi, Ryotaro Irie, Shigeru Koibuchi
  • Patent number: 4777111
    Abstract: This invention relates to a composition and method for enhancing the contrast of images of an underlying photolithographic layer. A photographic element, including a photoresist layer, is applied to a substrate. The photoresist layer contains a contrast-enhancing layer including at least one light-sensitive compound capable of producing acidic photoproducts upon exposure to actinic radiation, at least one indicator dye that changes color on exposure to acidic conditions and at least one polymeric binder soluble in water or weakly alkaline aqueous solutions. The photographic element is exposed to active radiation sufficient to cause photobleaching of the contrast enhancement layer and exposure of the photoresist layer. The photographic element is exposed to actinic radiation sufficient to cause photobleaching of the contrast enhancement layer and exposure of the photoresist layer.
    Type: Grant
    Filed: March 23, 1987
    Date of Patent: October 11, 1988
    Assignee: Fairmount Chemical Company, Inc.
    Inventors: David B. Blumel, Albert S. Deutsch
  • Patent number: 4772533
    Abstract: This invention relates to positive working photosensitized sheet constructions which, upon exposure to an actinic radiation source through a screened image, can accurately reproduce said image. The construction is useful as a color proofing film which can be employed to predict the image quality from a lithographic printing process.
    Type: Grant
    Filed: November 5, 1986
    Date of Patent: September 20, 1988
    Assignee: American Hoechst Corporation
    Inventors: Stephan J. W. Platzer, Gabor I. Koletar, Richard L. Shadrach
  • Patent number: 4772534
    Abstract: A light-sensitive composition containing a novel light-sensitive s-triazine compound represented by the formula (I) as a free radical-generating agent is disclosed. The s-triazine compound responds radiation in the range of the near ultraviolet to visible light, shows high sensitivity for photolysis and, therefore, the compositon has high light-sensitivity.
    Type: Grant
    Filed: September 5, 1986
    Date of Patent: September 20, 1988
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kouichi Kawamura, Hirokazu Kondo, Yoshimasa Aotani
  • Patent number: 4764450
    Abstract: A positive-working radiation-sensitive coating solution is disclosed which contains a radiation-sensitive compound, e.g., a 1,2-naphthoquinone diazide, or a radiation-sensitive combination of compounds, e.g., a compound with at least one C--O--C bond which can be split by acid and a compound which upon radiation forms a strong acid, and at least one organic solvent which comprises a mono-C.sub.1 to C.sub.4 -alkyl ether of 1,2-propanediol. The coating solution is less toxic and results in a better layer leveling than known positive-working photoresist solutions.
    Type: Grant
    Filed: December 29, 1986
    Date of Patent: August 16, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hans Ruckert, Ralf Ohlenmacher
  • Patent number: 4762766
    Abstract: A dry transfer film and a method for preparing transfer characters therefrom in which the transfer film includes a carrier layer, a photosensitized color carrying layer disposed adjacent to the carrier layer and a photosensitized adhesive layer disposed adjacent to the color carrying layer. Both the color carrying and adhesive layers are photosensitive to certain respective wavelengths of the electromagnetic spectrum so that when exposed to such wavelengths, they become soluble in a respective solvent or solvents. The unexposed portions of these layers remain insoluble in such solvents.
    Type: Grant
    Filed: January 14, 1986
    Date of Patent: August 9, 1988
    Assignee: Kroy Inc.
    Inventor: Kenneth M. Melbye
  • Patent number: 4758497
    Abstract: The invention features a new series of triazine compounds which are characterized by their ability to generate free radicals upon irradiation in a desired optical region, such that they are useful in the fabrication of lithographic plates having improved exposure speed, development, print-out, and contrast characteristics.
    Type: Grant
    Filed: April 17, 1987
    Date of Patent: July 19, 1988
    Assignee: Polychrome Corporation
    Inventors: Ajay Shah, William Rowe
  • Patent number: 4752552
    Abstract: A photosolubilizable composition contains both a compound capable of producing an acid by irradiation with actinic rays and a compound which has at least one silyl ether or silyl ester group capable of being decomposed by an acid; optionally, a compound having at least one silyl ether group has at least one hydrophilic group, providing for increased solubility in a developing solution under the action of an acid, thus enhancing the photosensitivity and the development latitude of the composition.
    Type: Grant
    Filed: August 12, 1987
    Date of Patent: June 21, 1988
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Toshiaki Aoai
  • 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: 4745045
    Abstract: A method which provides for a permanent planarization layer on a multilayer integrated circuit. The planarization layer resides above other circuit layers which reflect incident light. A layer of photoresist is formed over the planarization layers and imaged through a mask with circuit defining structure. During exposure of the photoresist, incident light passes through the planarization layer. Scattering from the boundary of the planarization layer and photoresist is minimized because the index of refraction of the planarization layer is substantially equal to the index of refraction of the photoresist. Light reflected from the underlaying layers is substantially absorbed by the planarization layer. Reduction of the reflected and scattered light results in improved resolution of developed images in photoresist.
    Type: Grant
    Filed: November 10, 1986
    Date of Patent: May 17, 1988
    Assignee: International Business Machines Corporation
    Inventors: Edward C. Fredericks, Giorgio G. Via
  • Patent number: 4738915
    Abstract: The invention provides an improvement over the conventional positive-working photoresist compositions comprising a novolac resin and an ester compound between 2,3,4-trihydroxybenzophenone and naphthoquinone-1,2-diazido-5-sulfonic acid in respect of scum formation in development and resistance of the patterned photoresist layer against heat and dry etching. The inventive composition comprises, in addition to the novolac resin and the ester compounds, 2,3,4-trihydroxybenzophenone in a specified amount relative to the ester compounds as a part of the photosensitive component which may be a reaction product obtained by the esterification reaction for the synthesis of the ester compounds containing unesterified 2,3,4-trihydroxybenzophenone.
    Type: Grant
    Filed: March 31, 1987
    Date of Patent: April 19, 1988
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Takashi Komine, Shingo Asaumi, Akira Yokota, Hisashi Nakane
  • Patent number: 4725526
    Abstract: In a process for reducing halations during the imagewise irradiation of a reproduction layer exposed through a planar image original, at least one lubricant either is contained in the layer or is interposed between the layer and the image original. Suitable lubricants include organic polysiloxanes, hydrocarbon polymers, polyaryl esters, and alkanoic acids or alkenoic acids having at least 9 carbon atoms. Excluded are lubricants comprising copolymers of dimethyl dichlorosilane, ethylene oxide and propylene oxide, provided they are located in the reproduction layer.
    Type: Grant
    Filed: August 19, 1985
    Date of Patent: February 16, 1988
    Assignee: Hoeschst Aktiengesellschaft
    Inventors: Werner Frass, Engelbert Pliefke