Sulfur Attached Directly To A Ring By Nonionic Bonding Patents (Class 534/557)
  • Patent number: 9923158
    Abstract: Disclosed are polymer-based dielectric compositions (e.g., formulations) and materials (e.g. films) and associated devices. The polymers generally include photocrosslinkable pendant groups; for example, the polymers can include one or more coumarin-containing pendant groups.
    Type: Grant
    Filed: August 25, 2014
    Date of Patent: March 20, 2018
    Assignees: BASF SE, FLEXTERRA, INC.
    Inventors: Jordan Quinn, He Yan, Yan Zheng, Christopher Newman, Silke Annika Koehler, Antonio Facchetti, Thomas Breiner
  • Patent number: 9188859
    Abstract: The present invention relates to a positive photosensitive resin composition and a method for forming patterns by using the same. The positive photosensitive resin composition includes a novolac resin (A), an ortho-naphthoquinone diazide sulfonic acid ester (B), a dye (C) and a solvent (D). The novolac resin (A) further includes hydroxy-type novolac resin (A-1), which is synthesized by condensing hydroxylbenzaldehyde compound with aromatic hydroxyl compound. The dye (C) includes at least one (C-1) selected from the group consisting of diazo dye, anthraquinone dye and chromium (III, Cr3+) azo dye, as well as triarylmethane dye (C-2). Since the positive photosensitive resin composition can form colorfully fine patterns on metal circuits, and such patterns are not decolored after being etched, thereby beneficially blocking the reflected light of the metal circuits.
    Type: Grant
    Filed: August 20, 2013
    Date of Patent: November 17, 2015
    Assignee: CHI MEI CORPORATION
    Inventors: Kai-Min Chen, Chun-An Shih
  • Patent number: 8530133
    Abstract: Embodiments in accordance with the present invention provide for norbornane-type ballast materials, norbornane-type photoactive compounds derived from such ballast materials and alkali-soluble positive-tone polymer compositions that encompass such norbornane-type photoactive compounds and one of a PBO or PNB resin.
    Type: Grant
    Filed: September 28, 2011
    Date of Patent: September 10, 2013
    Assignee: Promerus, LLC
    Inventors: Andrew Bell, Keitaro Seto, Hiroaki Makabe, Edmund Elce
  • Patent number: 8318402
    Abstract: Disclosed are a photosensitive compound and a method of manufacturing the same. The photosensitive is composed of a naphthoquinonediazide sulfonic ester compound having at least one naphthoquinonediazide sulfoxy group, and having either at least one carboxy group with 1 to 8 carbon atoms or at least one alkoxy group with 1 to 8 carbon atoms, in one molecule.
    Type: Grant
    Filed: December 30, 2009
    Date of Patent: November 27, 2012
    Assignee: Korea Kumho Petrochemical Co., Ltd.
    Inventors: Joo Hyeon Park, Seok Chan Kang, Jung Hwan Cho, Kyung Chul Son
  • Patent number: 8012664
    Abstract: A compound of the formula (I) where the symbols and indices are each defined as follows: A is A?, R or O—R; where R is a straight-chain, branched or cyclic, saturated or unsaturated aliphatic radical having 1-8 carbon atoms; A? is the same or different and is B is a bond, —O—C(O)—, —C(O)—O—, —O—C(O)—, —C(O)—NH—, —NH—C(O)—, —C(O)—O—CH2—CH(OH)—CH2—O, —O—CH2—CH(OH)—CH2—O—(O)C—, —O—C(O)—O—, —O—C(O)—NH— or —NH—C(O)—O—; R1 is H or OH; m is 1, 2, 3, 4 or 5; Y is n is a positive rational number ?3; E is the same or different and is —CH—CHR2—, —CHR2—CH2—, —CH2—CHR2—O—, —O—CHR2—CH2—, —(CH2)r—O— or —O—(CH2)—; R2 is H or CH3 and r is 1 or 4, is suitable as a light-sensitive component for photoresists.
    Type: Grant
    Filed: November 6, 2006
    Date of Patent: September 6, 2011
    Assignee: AZ Electronic Materials USA Corp.
    Inventors: Wolfgang Zahn, Ralf Grottenmüller, Dieter Wagner
  • Patent number: 7540883
    Abstract: The present invention discloses a reactive yellow dye composition comprising component (A) and component (B). The component (A) is a reactive azo dye represented by the following formula (I) or formula (II), The component (B) is a reactive azo dye represented by the following formula (III), wherein the substituents of the formulas (I), (II) and (III) are defined the same as in the specification. Moreover, the reactive yellow dye composition of the present invention has excellent build-up, wash-off and light fastness and can be applied with dyestuffs in other colors.
    Type: Grant
    Filed: August 2, 2007
    Date of Patent: June 2, 2009
    Assignee: Everlight USA, Inc.
    Inventors: Bao-Kun Lai, Cheng-Hsiang Hsu, Ya-Chi Tseng, Huei-Chin Huang
  • Patent number: 7524941
    Abstract: The present invention relates to methods for the preparation of chemically aminoacylated tRNAs for the purpose of introduction of markers into nascent proteins. The present invention also relates to methods for the non-radioactive labeling, detection, quantitation and isolation of nascent proteins translated in a cellular or cell-free translation system utilizing chemically aminoacylated tRNAs. tRNA molecules are misaminoacylated with non-radioactive markers which may be non-native amino acids, amino acid analogs or derivatives. Markers may comprise cleavable moieties, detectable labels, reporter properties wherein markers incorporated into protein can be distinguished from unincorporated markers, or coupling agents which facilitate the detection and isolation of nascent protein from other components of the translation system.
    Type: Grant
    Filed: September 11, 2007
    Date of Patent: April 28, 2009
    Assignee: Ambergen, Inc.
    Inventors: Jerzy Olejnik, Edyta Krzymanska-Olejnik, Sergey Mamaev, Kenneth J. Rothschild
  • Publication number: 20080288176
    Abstract: The present invention provides a method of using a physiologically-based pharmacokinetic model to select a prodrug molecule (NO—X) comprising a therapeutic agent X (e.g. nonsteroidal anti-inflammatory drug, (NSAID)) and an appropriate nitric oxide donor NO. The NSAID can be a non-selective or selective cyclooxygenase inhibitor or other biocompatible compound comprising a carboxyl group. The pharmacokinetic model uses in vitro and/or in silico data to estimate an optimal set of parameters that can predict whether a particular NO—X candidate is capable of producing desirable therapeutic effects, e.g. enhanced anti-inflammatory activity, reduced intestinal, cardiac and renal toxicity. Accordingly, the present invention can greatly enhance proper selection of an appropriate candidate for drug development, thereby minimizing development time and conserving costs.
    Type: Application
    Filed: October 13, 2006
    Publication date: November 20, 2008
    Inventors: Yun Kau Tam, Christopher Mark Diaper, Hugh A. Semple, Douglas Thacher Ridgway, Yi-Chan James Lin, Brian Duff Sloley
  • Patent number: 7355021
    Abstract: The present invention provides a single pot process for the preparation of diazonaphthoquinonesulfonyl ester, a useful organic material for micro electronic and dye industry. This study pertains to the one pot preparation of diazonaphthoquinonesulfonyl esters using the corresponding diazonaphthoquinine sulfonic acid or its sodium salt, diphosgene or triphosgene, variety of hydroxy compounds and tertiary organic base in an organic solvent medium.
    Type: Grant
    Filed: March 20, 2006
    Date of Patent: April 8, 2008
    Assignee: Council of Scientific & Industrial Research
    Inventors: Vummadi Venkat Reddy, Boddu Ananda Rao, Maruthi Janaki Ram Reddy, Chiguru Srinivas, Chilukuri Ramesh, Vaidya Jayathirtha Rao
  • Patent number: 6713225
    Abstract: The invention provides a 1,2-naphthoquinone-2-diazidesulfonate ester photosensitive agent which is useful as a photosensitive agent employed in a photoresist for producing semiconductor integrated circuits, liquid crystal displays, EL displays, etc., a method for producing the photosensitive agent, and a photoresist composition containing the photosensitive agent.
    Type: Grant
    Filed: March 11, 2003
    Date of Patent: March 30, 2004
    Assignee: Toyo Gosei Kogyo Co., Ltd.
    Inventors: Hirotada Iida, Miharu Suwa, Yuichi Hagiwara, Katsumi Tada, Suehiro Katori, Tsuneaki Miyazaki
  • Publication number: 20030175613
    Abstract: The invention provides a 1,2-naphthoquinone-2-diazidesulfonate ester photosensitive agent which is useful as a photosensitive agent employed in a photoresist for producing semiconductor integrated circuits, liquid crystal displays, EL displays, etc., a method for producing the photosensitive agent, and a photoresist composition containing the photosensitive agent.
    Type: Application
    Filed: March 11, 2003
    Publication date: September 18, 2003
    Inventors: Hirotada Iida, Miharu Suwa, Yuichi Hagiwara, Katsumi Tada, Suehiro Katori, Tsuneaki Miyazaki
  • Patent number: 6559291
    Abstract: The invention relates to a process for the preparation of diazonaphthoquinonesulfonylchlorides of the formula 1, 2 and 3 using diphosgene or triphosgene.
    Type: Grant
    Filed: March 25, 2002
    Date of Patent: May 6, 2003
    Assignee: Council of Scientific and Industrial Research
    Inventors: Vummadi Venkat Reddy, Maruthi Janaki Ram Reddy, Vaidya Jayathirtha Rao
  • Patent number: 6503682
    Abstract: A positive photoresist composition having improved sensitivity and resolution, a method of making the composition, and a method for forming a pattern during semiconductor processing using the composition are disclosed. The photoresist composition includes: (i) a photosensitive material obtained by mixing a first photosensitive compound represented by formula (1) and a second photosensitive compound represented by formulae (2a) or (2b); (ii) a resin; and (iii) a solvent. The invention enables the formation of patterns with an exceptional profile due to a high degree of sensitivity and resolution of the photoresist composition.
    Type: Grant
    Filed: March 30, 2000
    Date of Patent: January 7, 2003
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Young Ho Kim, Hoe Sik Chung, Sang Mun Chon, Boo Sup Lee
  • Patent number: 6448383
    Abstract: A method for producing a high-purity 1,2-naphthoquinonediazide photosensitive agent containing a low level of impurities, by condensing, in an organic solvent other than amide, polyhydric phenolic compound and 1,2-naphthoquinonediazide-sulfonic acid halide in the presence of organic amine; subsequently adding amide solvent to the resultant reaction mixture; and separating the resulting organic amine acid salt through filtration.
    Type: Grant
    Filed: May 8, 2001
    Date of Patent: September 10, 2002
    Assignee: Toyo Gosei Kogyo Co., Ltd.
    Inventors: Tomotaka Yamanaka, Masamichi Hayakawa
  • Patent number: 6420464
    Abstract: Resin compositions having a low viscosity, a low hygroscopicity, high adhesive properties and a high heat resistance as well as being light in weight and excellent in mechanical properties are provided. The resin compositions include polyhydric phenol compounds represented by the formula (1) and epoxy resins represented by the formula (3).
    Type: Grant
    Filed: April 24, 2000
    Date of Patent: July 16, 2002
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Kenichi Kuboki, Yoshitaka Kajiwara, Eiko Watanabe, Yoshio Shimamura, Katsuhiko Oshimi
  • Patent number: 6417178
    Abstract: Amyloid binding compounds which are derivatives of Chrysamine G, pharmaceutical compositions containing, and methods using such compounds to identify Alzheimer's brain in vivo and to diagnose other pathological conditions characterized by amyloidosis, such as Down's Syndrome are described. Pharmaceutical compositions containing Chrysamine G and derivatives thereof and methods using such compositions to prevent cell degeneration and amyloid-induced toxicity in amyloidosis associated conditions are also described. Methods using Chrysamine G derivatives to stain or detect amyloid deposits in biopsy or post-mortem tissue are also described. Methods using Chrysamine G derivatives to quantify amyloid deposits in homogenates of biopsy and post-mortem tissue are also described.
    Type: Grant
    Filed: November 6, 1997
    Date of Patent: July 9, 2002
    Assignee: University of Pittsburgh
    Inventors: William E. Klunk, Jay W. Pettegrew, Chester A. Mathis, Jr.
  • Publication number: 20010049433
    Abstract: A method for producing a high-purity 1,2-naphthoquinonediazide photosensitive agent containing a low level of impurities, by condensing, in an organic solvent other than amide, polyhydric phenolic compound and 1,2-naphthoquinonediazide-sulfonic acid halide in the presence of organic amine; subsequently adding amide solvent to the resultant reaction mixture; and separating the resulting organic amine acid salt through filtration.
    Type: Application
    Filed: May 8, 2001
    Publication date: December 6, 2001
    Inventors: Tomotaka Yamanaka, Masamichi Hayakawa
  • Patent number: 6274714
    Abstract: An effective method for producing 1,2-naphthoquinone-2-diazide-4-sulfonyl chloride at high yield, wherein formation of impurities is prevented. The method includes the following steps: 1,2-naphthoquinone-2-diazide is reacted with chlorosulfuric acid, to thereby produce a mixture of a sulfonated compound and a chlorosulfonated compound of the diazide; and to the mixture, at least one substance selected from among thionyl chloride and phosphorus pentachloride is added for further reaction, to thereby obtain 1,2-naphthoquinone-2-diazide-4-sulfonyl chloride.
    Type: Grant
    Filed: April 11, 2000
    Date of Patent: August 14, 2001
    Assignee: Toyo Gosei Kogyo Co., Ltd.
    Inventors: Hirotada Iida, Seiju Tobishima, Naoki Sato, Nobuhiro Yoneyama, Yuki Hotta, Toshio Itahana, Yuichi Hagiwara
  • Patent number: 6120969
    Abstract: Disclosed is, for example, bis(2,5-dimethyl-3-(2-hydroxy-5-ethylbenzyl)-4-hydroxyphenyl)methane and quinonediazide ester thereof. These are used for positive photoresist compositions. According to the invention, positive photoresist compositions having a high definition, a high sensitivity and a large exposure margin can be provided.
    Type: Grant
    Filed: April 2, 1999
    Date of Patent: September 19, 2000
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Mitsuo Hagihara, Kousuke Doi, Hidekatsu Kohara, Toshimasa Nakayama, Tetsuya Nakajima
  • Patent number: 6077941
    Abstract: An effective method for producing a 1,2-naphthoquinone-2-diazide or a sulfo-substituted compound thereof from a 2-diazo-1-naphthalenesulfonic acid or a sulfo-substituted compound thereof. A 1,2-naphthoquinone-2-diazide derivative or a sulfo-substituted compound thereof is derived from a 2-diazo-1-naphthalenesulfonic acid or a sulfo-substituted compound thereof by use of an aqueous alkaline solution containing iodine; an aqueous alkaline solution containing iodine which is dissolved in an organic solvent; or an aqueous alkaline solution containing an oxidizing agent and iodine or an iodine compound.
    Type: Grant
    Filed: June 15, 1999
    Date of Patent: June 20, 2000
    Assignee: Toyo Gosei Kogyo Co., Ltd.
    Inventors: Hirotada Iida, Nobuhiro Yoneyama, Seiju Tobishima, Toshio Itahana, Kunihiko Kojima
  • Patent number: 6051358
    Abstract: An unsymetrical photoactive compound having the formula ##STR1## where Z is hydrogen, a hydrocarbon having from 1 to 8 carbon atoms, or halogen; D is hydrogen or diazo-oxo-naphthalene-sulfonyl; n is equal to 1 to 4; R.sub.1, R.sub.5 and R.sub.6 are independently a hydrocarbon or halogen; R.sub.2 is the same as R.sub.1 or hydrogen; each R.sub.3 is the same as R.sub.2, hydroxyl or --OD; and each R.sub.4 is the same as R.sub.2 or another substituent provided that at least one R.sub.2, or one or both R.sub.4 is other than hydrogen, at least 2 Ds are diazo-oxo-sulfonyl group and at least 50 mole percent of the mixture conforms to the formula where n equals 1. The compounds of the invention are suitable for formation of storage stable photoresist compositions.
    Type: Grant
    Filed: November 4, 1997
    Date of Patent: April 18, 2000
    Assignee: Shipley Company, L.L.C.
    Inventors: Anthony Zampini, Harold F. Sandford
  • Patent number: 6040107
    Abstract: A photosensitive compound comprising at least one o-quinonediazide sulfonic acid ester of a phenolic compound, said esters selected from the group consisting of formula (II): ##STR1## wherein the photosensitive compound is used in a radiation sensitive composition and a process for forming a positive patterned image.
    Type: Grant
    Filed: February 6, 1998
    Date of Patent: March 21, 2000
    Assignee: Olin Microelectronic Chemicals, Inc.
    Inventors: Andrew J. Blakeney, Arturo N. Medina, Medhat A. Toukhy, Lawrence Ferreira, Alfred T. Jeffries, III, Ahmad A. Naiini
  • Patent number: 5945516
    Abstract: A method for converting a kinetically stable multiester of a naphthoquinone and an o-quinone diazide sulfonyl halide to a thermodynamically stable compound. The method comprises the steps of dissolving a phenol having at least two free phenolic hydroxyl groups and an o-naphthoquinone diazide sulfonyl halide in an aprotic solvent in the presence of a strong base, there being at least one mole of said naphthoquinone diazide sulfonyl halide per mole of phenol, reacting said phenol with said o-napthoquinone diazide sulfonyl halide until essentially of said o-naphthoquinone diazide sulfonyl halide is reacted with said polyhydroxy phenol, and following completion of said reaction, permitting the reaction product to remain in said solvent for a period of time of at least 15 minutes before recovering said photoactive compound The photoactive compound formed by the process is suitable for the formation of photoresists and is less apt to precipitate from solution during storage.
    Type: Grant
    Filed: May 20, 1998
    Date of Patent: August 31, 1999
    Assignee: Shipley Company, L.L.C.
    Inventors: Harold F. Sandford, Anthony Zampini
  • Patent number: 5936071
    Abstract: The present invention provides for process of preparing a photoactive ester compound of high purity using a solid base catalyst, preferably an anionic exchange resin. The invention further provides for preparing and imaging a photosensitive composition comprising such a photoactive compound, a film-forming resin and a solvent composition.
    Type: Grant
    Filed: February 2, 1998
    Date of Patent: August 10, 1999
    Assignee: Clariant Finance (BVI) Limited
    Inventor: Joseph E. Oberlander
  • Patent number: 5866724
    Abstract: A positive photoresist compositions comprising, as a photosensitizer, a quinonediazide sulfonic acid ester of a phenol compound represented by the following formula (I): ##STR1## wherein Q.sup.1, Q.sup.2, Q.sup.3, Q.sup.4, Q.sup.5, Q.sup.6, Q.sup.7, Q.sup.8, Q.sup.9 and Q.sup.10 independently represent hydrogen, alkyl having 1-6 carbon atoms or phenyl, or Q.sup.1 and Q.sup.2, Q.sup.3 and Q.sup.4, Q.sup.5 and Q.sup.6, Q.sup.7 and Q.sup.8, or Q.sup.9 and Q.sup.10 may form a cycloalkane ring having 6 or less carbon atoms together with a carbon atoms to which they are connected, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11, R.sup.12, R.sup.13, R.sup.14, R.sup.15 and R.sup.16 independently represent hydrogen, hydroxyl, alkyl having 1-6 carbon atoms or phenyl; andm and n independently represent a number of 0 or 1;and an alkali soluble resin;and a quinonediazide sulfonic acid ester of a phenol compound of formula (I).
    Type: Grant
    Filed: October 17, 1996
    Date of Patent: February 2, 1999
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Haruyoshi Osaki, Hiroki Inoue
  • Patent number: 5821345
    Abstract: A method for converting a kinetically stable multiester of a naphthoquinone and an o-quinone diazide sulfonyl halide to a thermodynamically stable compound. The method comprises the steps of dissolving a phenol having at least two free phenolic hydroxyl groups and an o-naphthoquinone diazide sulfonyl halide in an aprotic solvent in the presence of a strong base, there being at least one mole of said naphthoquinone diazide sulfonyl halide per mole of phenol, reacting said phenol with said o-napthoquinone diazide sulfonyl halide until essentially of said o-naphthoquinone diazide sulfonyl halide is reacted with said polyhydroxy phenol, and following completion of said reaction, permitting the reaction product to remain in said solvent for a period of time of at least 15 minutes before recovering said photoactive compound. The photoactive compound formed by the process is suitable for the formation of photoresists and is less apt to precipitate from solution during storage.
    Type: Grant
    Filed: March 12, 1996
    Date of Patent: October 13, 1998
    Assignee: Shipley Company, L.L.C.
    Inventors: Harold F. Sandford, Anthony Zampini
  • Patent number: 5795878
    Abstract: A phenylazoxycyanide compound of formula I ##STR1## is useful as an antimicrobial and fungicidal composition. A method for using the antimicrobial and fungicidal compositions, and for manufacturing the compound is also disclosed.
    Type: Grant
    Filed: June 6, 1997
    Date of Patent: August 18, 1998
    Assignee: American Cyanamid Company
    Inventor: Werner Simon
  • Patent number: 5773591
    Abstract: A novel process for preparing sulfonic acid esters and amides of benzo-heterocyclic diazo diketo compounds, such as substituted diazo-4-oxo-3,4-dihydrocoumarins, which are useful synthetic intermediates in a wide variety of applications including photoresists, opto-electronics, agricultural, and pharmaceutical applications is disclosed and claimed. The process comprises the steps of (a) subjecting a substituted benzo-heterocyclic .beta.-keto-enol compound to suitable diazo transfer conditions in the presence of a diazo transfer agent; (b) subjecting the so formed diazo diketo compound to suitable halosulfonation conditions in the presence of a halosulfonation agent; and (c) subjecting the so formed halosulfonyl aromatic compound to suitable substitution reaction in the presence of an alcohol or an amine to form the corresponding sulfonic acid ester or amide of benzo-heterocyclic diazo diketo compound.
    Type: Grant
    Filed: March 7, 1997
    Date of Patent: June 30, 1998
    Assignee: Hoechst Celanese Corp.
    Inventors: Mohammad Aslam, Michael T. Sheehan, George Kvakovszky
  • Patent number: 5739295
    Abstract: A new class of 3-diazo-3,4-dihydrocoumarin compounds which are useful as photoactive compounds in a wide variety of applications including photoresists and other opto-electronic applications are disclosed and claimed. Preferred embodiments include 6-sulfonyl-3-diazo-4-oxo-3,4-dihydrocoumarin esters. These compounds exhibit very high photosensitivity in the deep ultraviolet (DUV) region (ca. 250 nm), and therefore, are useful as photoactive compounds in DUV photoresist formulations.
    Type: Grant
    Filed: March 7, 1997
    Date of Patent: April 14, 1998
    Assignee: Hoechst Celanese Corporation
    Inventors: Mohammad Aslam, Michael T. Sheehan, George Kvakovszky, Kenneth G. Davenport, Douglas J. Gordon
  • Patent number: 5726217
    Abstract: A tetraphenol compound represented by the formula (I): ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 represent hydrogen 1,2-naphthoquinonediazide-4-sulfonyl or 1,2-naphthoquinonediazide-5-sulfonyl and a method for producing the compound are provided, and the compound can be used as a photosensitizer for a positive resist which exhibits superior properties.
    Type: Grant
    Filed: March 8, 1996
    Date of Patent: March 10, 1998
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Ichikawa, Haruyoshi Osaki, Jun Tomioka
  • Patent number: 5726295
    Abstract: A new class of 3,4-dihydrocoumarin derivatives which are useful as photoactive compounds in a wide variety of applications including photoresists and other opto-electronic applications are disclosed and claimed. Preferred embodiments include ether, ester, carbonate, and sulfonate derivatives of 5-hydroxy, 6-hydroxy, and 7-hydroxy-3-diazo-4-oxo-3,4-dihydrocoumarins. These compounds exhibit very high photosensitivity in the deep ultraviolet (DUV) region (ca. 250 nm), and therefore, are useful as photoactive compounds in DUV photoresist formulations.
    Type: Grant
    Filed: March 7, 1997
    Date of Patent: March 10, 1998
    Assignee: Hoechst Celanese Corp.
    Inventors: Mohammad Aslam, Michael T. Sheehan, Debasish Kuila
  • Patent number: 5726296
    Abstract: Novel processes for the preparation of a new class of coumarin derivatives, which are useful as photoactive compounds in a wide variety of applications including photoresists and other opto-electronic applications, are disclosed and claimed. The process involves a multi-step synthetic method for the preparation of ether, ester, carbonate, or sulfonate derivative of 5-hydroxy, 6-hydroxy, or 7-hydroxy-3-diazo-4-oxo-3,4-dihydrocoumarin starting from the corresponding dihydroxyacetophenone. The compounds formed from the process of the present invention exhibit very high photosensitivity in the deep ultraviolet (DUV) region (ca. 250 nm), and therefore, are useful as photoactive compounds in DUV photoresist formulations.
    Type: Grant
    Filed: March 7, 1997
    Date of Patent: March 10, 1998
    Assignee: Hoechst Celanese Corp.
    Inventors: Mohammad Aslam, Michael T. Sheehan, Debasish Kuila
  • Patent number: 5677103
    Abstract: A positive photoresist composition which is of high resolution, high sensitivity and wide focusing range and suitable for high integration of semiconductor devices and shows superior resist pattern profile, comprising quinonediazide sulfonic acid ester as a photoresist, an alkali soluble resin, a solvent, and additives, said quinonediazide sulfonic acid ester being prepared through the esterification of 1,2-naphthoquinonediazidesulfonyl halide or 1,2-benzoquinonediazidesulfonyl halide with an aromatic hydroxy compound represented by the following structural formula I: ##STR1## wherein R.sub.1 and R.sub.2 are independently hydrogen, halogen, an alkyl group or an alkoxy group; a is an integer of 1 to 3; b is an integer of 1 to 8; c is an integer of 1 to 12; and R.sub.3 is an alkyl group containing ether, mercapthane, sulfoxide, sulfone, aryl group or hydroxy group.
    Type: Grant
    Filed: September 30, 1996
    Date of Patent: October 14, 1997
    Assignee: Korea Kumho Petrochemical Co., Ltd.
    Inventors: Seong-Ju Kim, Joo-Hyeon Park, Ji-Hong Kim, Sun-Yi Park
  • Patent number: 5644038
    Abstract: Quinone diazo compounds having bonded to the diazo ring or directly bonded to a ring of the compound, certain non-metallic atoms that improve the photosensitivity thereof are provided. These quinone diazo compounds are useful as photoactive compounds in photoresist compositions, and particularly positive photoresist composition employed in x-ray or electron beam radiation. Also provided is a method for preparing compounds of the present invention.
    Type: Grant
    Filed: March 15, 1996
    Date of Patent: July 1, 1997
    Assignee: International Business Machines Corporation
    Inventors: Ari Aviram, William Ross Brunsvold, Daniel Bucca, Willard Earl Conley, Jr., David Earle Seeger
  • Patent number: 5629128
    Abstract: A positive photoresist composition is described, which comprises an alkali-soluble resin and 1,2-naphthoquinone-diazido-5-(and/or -4-)sulfonate of a polyhydroxy compound represented by the following formula (I): ##STR1## wherein R.sub.1 to R.sub.11 are the same or different and each represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an alkoxyl group, an acyl group or a cycloalkyl group, provided that at least one of R.sub.1 to R.sub.11 is a cycloalkyl group; A represents -CH(R.sub.12)-, in which R.sub.12 represents a hydrogen atom or an alkyl group; and m represents 2 or 3.
    Type: Grant
    Filed: September 20, 1995
    Date of Patent: May 13, 1997
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Koji Shirakawa, Kenichiro Sato, Kunihiko Kodama, Yasumasa Kawabe, Shinji Sakaguchi
  • Patent number: 5618932
    Abstract: A new photoactive compound for use in the formulation of a photoresist comprises a bisphenol compound having an alkyl linkage substituted with a heterocyclic group. The new photoactive compound may be admixed with an alkali soluble resin to formulate a photoresist composition. The new photoactive compounds exhibit enhanced long term solubility in conventional photoresist solvents.
    Type: Grant
    Filed: May 24, 1995
    Date of Patent: April 8, 1997
    Assignee: Shipley Company, L.L.C.
    Inventors: Anthony Zampini, Ashish Pandya
  • Patent number: 5612164
    Abstract: A photosensitizer comprising a trishydroxyphenylethane 80/20 to 50/50 2,1,5-/2,1,4-diazonaphthoquinone sulfonate, and a trishydroxybenzophenone 0/100 to 20/80 2,1,5-/2,1,4-diazonaphthoquinone sulfate, and a photoresist composition containing such photosensitizer, the photosensitizer being present in the photoresist composition in an amount sufficient to uniformly photosensitize the photoresist composition; and a water insoluble, aqueous alkali soluble novolak resin, the novolak resin being present in the photoresist composition in an amount sufficient to form a substantially uniform photoresist composition.
    Type: Grant
    Filed: February 9, 1995
    Date of Patent: March 18, 1997
    Assignee: Hoechst Celanese Corporation
    Inventors: Anthony Canize, Stanley A. Ficner, Ping-Hung Lu, Walter Spiess
  • Patent number: 5609982
    Abstract: The present invention provides a positive-working photoresist composition comprising an alkali-soluble resin and a 1,2-naphthoquinonediazide-5-(and/or -4-)sulfonic ester of a specific water-insoluble alkali-soluble low molecular compound, wherein the high-performance liquid chromatography of the ester with an ultraviolet ray at 254 nm shows that the patterns corresponding to the diester components and complete ester component of the ester each fall within the specific range and a positive-working photoresist composition comprising a water-insoluble alkali-soluble resin, a water-insoluble alkali-soluble low molecular compound, and an ionization-sensitive radioactive compound which comprises a mixture of a naphthoquinone-diazidesulfonic diester of a water-insoluble alkali-soluble low molecular compound having three phenolic hydroxyl groups as an ionization-sensitive radioactive compound (A) and a naphthoquinonediazidesulfonic diester of a water-insoluble alkali-soluble low molecular compound having four phenoli
    Type: Grant
    Filed: December 16, 1994
    Date of Patent: March 11, 1997
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kenichiro Sato, Yasumasa Kawabe, Toshiaki Aoai, Shinji Sakaguchi
  • Patent number: 5609983
    Abstract: There is provided a positive working photosensitive composition suitable for photosensitive lithographic printing plate or photoresist for fine processing, which comprises a quinonediazide ester compound having the structure characterized by containing in the same molecule both quinonediazide structure and N-sulfonylamide [--C(.dbd.O)--NHSO.sub.2 --] or sulfonamide [--NHSO.sub.2 --] structure which are positioned independently of each other.
    Type: Grant
    Filed: May 24, 1995
    Date of Patent: March 11, 1997
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Koichi Kawamura, Kenichiro Sato, Shinji Sakaguchi
  • Patent number: 5563018
    Abstract: The invention relates to 2,3,4-trihydroxy-3'-methyl-, -ethyl-, -propyl- or -isopropylbenzophenone which is completely esterified with (1,2-naphthoquinone 2-diazide)-4-sulfonic acid and/or (7-methoxy-1,2-naphthoquinone 2-diazide)-4-sulfonic acid, a radiation-sensitive mixture prepared therewith, and a radiation-sensitive recording material comprising a substrate and a radiation-sensitive layer which is composed of the mixture according to the invention.
    Type: Grant
    Filed: March 17, 1993
    Date of Patent: October 8, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gerhard Buhr, Wolfgang Zahn, Fritz Erdmann, Siegfried Scheler
  • Patent number: 5554481
    Abstract: A positive working photoresist composition sensitive to radiation, having high resolving power, high sensitivity, and excellent storage stability, and further forming a pattern capable of accurately reproducing a mask size in a wide range of photomask line width. The present invention has been obtained by a composition containing at least one of a 1,2-napthoquinonediazido-5-sulfonic acid ester of a polyhydroxy compound and a 1,2-napthoquinonediazido-4-sulfonic acid ester of a polyhydroxy compound in combination with at least one alkali-soluble resin.
    Type: Grant
    Filed: December 22, 1994
    Date of Patent: September 10, 1996
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Yasumasa Kawabe, Kenichiro Satoh, Toshiaki Aoai
  • Patent number: 5552256
    Abstract: Quinone diazo compounds having bonded to the diazo ring or directly bonded to a ring of the compound, certain non-metallic atoms that improve the photosensitivity thereof are provided. These quinone diazo compounds are useful as photoactive compounds in photoresist compositions, and particularly positive photoresist composition employed in x-ray or electron beam radiation. Also provided is a method for preparing compounds of the present invention.
    Type: Grant
    Filed: September 29, 1994
    Date of Patent: September 3, 1996
    Assignee: International Business Machines Corporation
    Inventors: Ari Aviram, William R. Brunsvold, Daniel Bucca, Willard E. Conley, Jr., David E. Seeger
  • Patent number: 5541033
    Abstract: A photosensitive compound comprising at least one o-quinonediazide sulfonic acid ester of a phenolic compound, said esters selected from the group consisting of formulae (IB) and (IIB): ##STR1## wherein the photosensitive compound is used in a positive photoresist composition and process for forming patterned image. Further the invention is drawn to a positive photoresist composition comprising an alkali-soluble resin and quinone diazide sulfonic acid triesters and diesters characterized by their HPLC peak areas.
    Type: Grant
    Filed: February 1, 1995
    Date of Patent: July 30, 1996
    Assignee: OCG Microelectronic Materials, Inc.
    Inventors: Andrew J. Blakeney, Arturo N. Medina, Medhat A. Toukhy, Lawrence Ferreira, Sobhy Tadros
  • Patent number: 5534382
    Abstract: Disclosed is a positive photoresist composition comprising an alkali-soluble resin and the 1,2-naphthoquinonediazido-5-(and/or -4-)sulfonate acid ester of a polyhydroxy compound represented by formula (I): ##STR1## wherein R.sub.1 to R.sub.3 may be the same or different and each represents a hydrogen atom, a halogen atom, a hydroxyl group, an alkyl group, or an alkoxy group; and m, n and o each represent an integer of from 1 to 3. The photoresist composition has a high resolving power and a less layer thickness reliance of the resolving power, and a wide development latitude, is reluctant to form a development residue, and further has a very excellent storage stability, and does not deposit the photosensitive material and does not form microgels, i.e., shows no increase in the particles, with the passage of time.
    Type: Grant
    Filed: March 27, 1995
    Date of Patent: July 9, 1996
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Yasumasa Kawabe, Kenichiro Sato
  • Patent number: 5532107
    Abstract: Disclosed herein is a positive resist composition comprising an alkali-soluble phenolic resin and a photosensitive agent, characterized in that the positive resist composition contains, as the photosensitive agent, the quinonediazide sulfonate of at least one of phenolic compounds represented by the following general formulae (I) and (II): ##STR1## wherein R.sub.1 through R.sub.4 mean individually a hydrogen or halogen atom, a hydroxyl group, an alkyl or alkenyl group having 1-3 carbon atoms, or a hydroxyalkyl group having 1-3 carbon atoms and may be equal to or different from one another, and R.sub.5 denotes a hydrogen atom, an alkyl or alkenyl group having 1-3 carbon atoms, or an aryl group with the proviso that the number of hydroxyl groups is 3 or 4; and ##STR2## wherein R.sub.6 through R.sub.9 mean individually a hydrogen or halogen atom, an alkyl or alkenyl group having 1-3 carbon atoms, or a hydroxyalkyl group having 1-3 carbon atoms and may be equal to or different from one another, and R.sub.
    Type: Grant
    Filed: April 13, 1994
    Date of Patent: July 2, 1996
    Assignee: Nippon Zeon Co., Ltd.
    Inventors: Masayuki Oie, Shoji Kawata, Takamasa Yamada, Shinya Ikeda
  • Patent number: 5523396
    Abstract: A process for synthesizing a quinonediazide ester is disclosed in which the esterification reaction of a polyhydroxy compound with 1,2-naphthoquinonediazide-5-(and/or -4-)sulfonyl chloride is carried out in the presence of a base catalyst comprising a basic compound represented by formula (I) or (II): ##STR1## wherein R.sub.1 to R.sub.15 are defined in the disclosure. A positive working photoresist containing the ester is also disclosed. The process is capable of highly selectively yielding the desired photosensitive material containing specific unreacted hydroxyl group(s). The photoresist has high resolving power with reduced film thickness dependence of the resolving power, is less apt to leave a development residue, and has excellent storage stability for prolonged period of time.
    Type: Grant
    Filed: September 21, 1995
    Date of Patent: June 4, 1996
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kenichiro Sato, Yasumasa Kawabe, Toshiaki Aoai
  • Patent number: 5518859
    Abstract: A positive-type photosensitive electrodeposition coating composition comprising a water-soluble or water-dispersible resin having an ionic group and containing at least one modified quinonediazidesulfone unit represented by the following formula (I) or (II) ##STR1## wherein R.sub.1 represents ##STR2## R.sub.2 represents a hydrogen atom, an alkyl group, a cycloalkyl group or an alkyl ether group, andR.sub.3 represents an alkylene group, a cycloalkylene group, an alkylene ether group, a phenylene group which may optionally be substituted with an alkyl group having 1 to 20 carbon atoms, or an alkylene, cycloalkylene or alkylene ether group containing in its chain a phenylene group which may optionally be substituted with an alkyl group having 1 to 20 carbon atoms, in the molecule.
    Type: Grant
    Filed: March 16, 1995
    Date of Patent: May 21, 1996
    Assignee: Kansai Paint Co., Ltd.
    Inventors: Naozumi Iwasawa, Junichi Higashi
  • Patent number: 5514515
    Abstract: A new photoactive compound for use in the formulation of a photoresist comprises a bisphenol compound having an alkyl linkage substituted with a heterocyclic group. The new photoactive compound may be admixed with an alkali soluble resin to formulate a photoresist composition. The new photoactive compounds exhibit enhanced long term solubility in conventional photoresist solvents.
    Type: Grant
    Filed: May 24, 1995
    Date of Patent: May 7, 1996
    Assignee: Shipley Company, L.L.C.
    Inventors: Anthony Zampini, Ashish Pandya
  • Patent number: 5439774
    Abstract: A positive-type photosensitive electrodeposition coating composition comprising a water-soluble or water-dispersible resin having an ionic group and containing at least one modified quinonediazidesulfone unit represented by the following formula (I) or (II) ##STR1## wherein R.sub.1 represents ##STR2## R.sub.2 represents a hydrogen atom, an alkyl group, a cycloalkyl group or an alkyl ether group, andR.sub.3 represents an alkylene group, a cycloalkylene group, an alkylene ether group,a phenylene group which may optionally be substituted with an alkyl group having 1 to 20 carbon atoms, or an alkylene, cycloalkylene or alkylene ether group containing in its chain a phenylene group which may optionally be substituted with an alkyl group having 1 to 20 carbon atoms, in the molecule.
    Type: Grant
    Filed: September 28, 1994
    Date of Patent: August 8, 1995
    Assignee: Kansai Paint Co., Ltd.
    Inventors: Naozumi Iwasawa, Junichi Higashi
  • Patent number: 5436107
    Abstract: A positive resist composition which comprises, in admixture, an alkali-soluble resin; at least one quinone diazide sulfonate of a polyhydric phenol compound of the formula: ##STR1## wherein R.sub.1 to R.sub.5 are independently a hydrogen atom, an alkyl group, an alkenyl group, a cycloalkyl group or an aryl group, provided that at least one of R.sub.1 and R.sub.2 is an alkyl group, an alkenyl group, a cycloalkyl group or an aryl group; anda quinone diazide sulfonate of a phenol compound of the formula ##STR2## wherein R.sub.6 to R.sub.10 are independently a hydrogen atom, an alkyl group, an alkenyl group, a cycloalkyl group or an aryl group, provided that at least one of R.sub.6 and R.sub.7 is an alkyl group, an alkenyl group, a cycloalkyl group or an aryl group.
    Type: Grant
    Filed: March 18, 1992
    Date of Patent: July 25, 1995
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Jun Tomioka, Yasunori Uetani, Hirotoshi Nakanishi, Ryotaro Hanawa, Ayako Ida