Polymeric Mixture Patents (Class 430/192)
  • 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: 5508141
    Abstract: A coating of resin and photoactive functionality is autodeposited from an emulsion onto a metallic substrate in order to selectively protect the substrate from corrosive environments such as etchant processes. An acid and oxidizing agent are included in the emulsion so that when the substrate is immersed in the emulsion the resin and photoactive functionality autodeposits. The resulting coating can be exposed to actinic radiation in an image-wise fashion and developed in an alkaline solution to develop the image created. In instances where the emulsion and process are used to make circuit boards, the metallic surface uncovered during developing is then etched away, leaving only the coated sections of the surface. The resulting coated surfaces will be the circuit traces of the circuit board.
    Type: Grant
    Filed: December 2, 1994
    Date of Patent: April 16, 1996
    Assignee: W. R. Grace & Co.-Conn.
    Inventors: Daniel J. Hart, Alan F. Becknell, Betsy Elzufon, John S. Hallock, Alan R. Browne
  • Patent number: 5501936
    Abstract: An improved positive-working photoresist composition useful in the fine patterning work of a resist layer is proposed which is capable of giving a patterned resist layer having excellent resolution, heat resistance and orthogonality of the cross sectional profile of a line pattern with a high sensitivity to actinic rays and a wide range of the focusing depth. The photoresist composition comprises, as a uniform mixture in the form of a solution, (a) an alkali-soluble novolac resin, (b) a naphthoquinone-1,2-diazido group-containing compound as a photosensitizing ingredient and (c) a specific phenolic triphenyl methane compound substituted by cyclohexyl groups on two of the phenyl groups, such as bis(3-cyclohexyl-4-hydroxy-6-methylphenyl)-3,4-dihydroxyphenyl methane or bis(3-cyclohexyl-6-hydroxy-4-methylphenyl)-3,4-dihydroxyphenyl methane, in a specified amount.
    Type: Grant
    Filed: December 23, 1994
    Date of Patent: March 26, 1996
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hiroshi Hosoda, Remi Numata, Kousuke Doi, Nobuo Tokutake, Hidekatsu Kohara, Toshimasa Nakayama
  • Patent number: 5498498
    Abstract: Disclosed is a photosensitive resin composition for use in a light-shielding film, comprising a photosensitive resin and a light-shielding coloring material, wherein light transmission properties after formation of the light-shielding film are controlled by the light-shielding coloring material so that (i) the light transmission through the light-shielding film is 1% or more in at least one wavelength of a light wavelength region of from 330 nm to less than 425 nm, and (ii) the light transmission through the light-shielding film is 2% or less in a light wavelength region of from 425 to 650 nm.
    Type: Grant
    Filed: August 1, 1994
    Date of Patent: March 12, 1996
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Kiyoshi Uchikawa, Hiroshi Komano, Toshimi Aoyama, Katsuyuki Ohta
  • Patent number: 5494773
    Abstract: A positive photoresist composition comprising an alkali-soluble novolak resin and a 1,2-quinonediazide compound is described, wherein the alkali-soluble novolak resin contains a novolak resin to be obtained by condensing a mixture of (a) at least one phenol represented by the following formula (1) and at least one compound represented by the following formula (2) and (b) at least one aldehyde: ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are the same or different and each represents a hydrogen atom, a hydroxyl group, a halogen atom, an alkyl group, an alkoxy group, an alkenyl group, an aryl group, an aralkyl group, an alkoxycarbonyl group or an arylcarbonyl group; R.sub.4, R.sub.5, R.sub.6 and R.sub.7 are the same or different and each represents a hydrogen atom, a hydroxyl group, a halogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, an alkenyl group, an aryl group or an aralkyl group; and n represents an integer of from 4 to 7.
    Type: Grant
    Filed: March 6, 1995
    Date of Patent: February 27, 1996
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Shiro Tan, Yasumasa Kawabe, Tadayoshi Kokubo
  • Patent number: 5494785
    Abstract: A phenolic novolak composition prepared by a process comprising the steps of:(1) reacting a first phenolic monomer comprising a major portion of at least one trifunctional phenolic monomer with a first aldehyde source in the absence of a catalyst at a reaction temperature from about 100.degree. C. to about 200.degree. C. and at a reaction pressure of about 2 to about 15 atmospheres to form a phenolic oligomer having a weight average molecular weight from about 500 to about 2,000, having ortho-ortho bonding of about 55% to about 75% of the methylene bonds between the phenolic moieties; and having a time to clear of less than 125 seconds per micron; wherein the mole ratio of said first aldehyde source to said first phenolic monomer is from about 0.3:1.0 to about 0.55:1.0; and(2) then reacting said oligomer with an optional second phenolic source and a second aldehyde source at a temperature from about 80.degree. C. to about 150.degree. C.
    Type: Grant
    Filed: January 17, 1995
    Date of Patent: February 27, 1996
    Assignee: OCG Microelectronic Materials, Inc.
    Inventors: Joseph J. Sizensky, Thomas R. Sarubbi, Medhat A. Toukhy
  • Patent number: 5492790
    Abstract: A positive photoresist composition applicable for printing and making gas sensors, color filters and the like, without difficulties in process-control for making them, without any deteriorations in the good properties that photoresists originally have, which comprises a compound having at least one group selected from a sulfonamide, carboxylic acid amide and ureido which are substituted at one position, a dissolution inhibitor and an organic solvent and with which a thin color filter having various excellent properties such as color darkness and color reproductivity can be obtained.
    Type: Grant
    Filed: June 13, 1994
    Date of Patent: February 20, 1996
    Assignee: Sumitomo Chemical Company, Limited
    Inventor: Yoshiki Hishiro
  • Patent number: 5482816
    Abstract: A radiation-sensitive composition comprising (A) a polymer having a recurring unit represented by formula (1): ##STR1## wherein R.sup.1 represents a substituted methyl group, a substituted ethyl group, a silyl group, a germyl group or an alkoxycarbonyl group, and R.sup.2 represents --OR.sup.3 or --NR.sup.4 R.sup.5 in which R.sup.3 is a hydrogen atom, a straight-chain alkyl group, a cyclic alkyl group, an aryl group, an aralkyl group, a substituted methyl group, a substituted ethyl group, a silyl group, a germyl group or an alkoxycarbonyl group, and R.sup.4 and R.sup.5, which may be the same or different, are hydrogen atoms, straight-chain alkyl groups, cyclic alkyl groups, aralkyl groups or aryl groups, and (B) a radiation-sensitive acid forming agent.
    Type: Grant
    Filed: June 21, 1994
    Date of Patent: January 9, 1996
    Assignee: Japan Synthetic Rubber Co., Ltd.
    Inventors: Makoto Murata, Mikio Yamachika, Yoshiji Yumoto, Takao Miura
  • Patent number: 5478691
    Abstract: A radiation-sensitive resin composition comprising an alkali-soluble novolak resin and a 1,2-quinonediazide compound, wherein the alakli-soluble novolak resin comprises a mixture of:95-50 parts by weight of Resin A having a standard polystyrene-reduced weight-average molecular weight of 2,000-20,000 [Resin A is at least one resin selected from the group consisting of a resin obtained by polycondensation of m-cresol and at least one phenol represented by the structural formula (I) or (I'): ##STR1## wherein m is 2 or 3, with at least one aldehyde and a resin obtained by polycondensation of m-cresol, p-cresol and at least one phenol repreented by the above structural formula (I) or (I') with at least one aldehyde] and5-50 parts by weight of Resin B having a standard polystyrene-reduced weight-average molecular weight of 200-2,000 [Resin B is a resin obtained by polycondensation of at least one phenol represented by the structural formula (II): ##STR2## wherein n is 0, 1, 2 or 3, with at least one aldehyde].
    Type: Grant
    Filed: June 13, 1994
    Date of Patent: December 26, 1995
    Assignee: Japan Synthetic Rubber Co., Ltd.
    Inventors: Satoshi Miyashita, Akihiro Yamanouchi, Ikuo Nozue, Takao Miura
  • Patent number: 5478690
    Abstract: Disclosed is an alkali developable photosensitive resin composition useful for an offset printing plate, which has excellent developability and provides long life of a developer. The photosensitive resin composition comprising:(a) an alkali-soluble type binder resin,(b) a photosensitive substance, and(c) a dye;said binder resin (a) having an ampho-ionic group represented by the formula: ##STR1## [wherein R.sup.1 is H or a C.sub.1-10 alkyl group which optionally has a substituent or a functional group in a chain, R is a substituted or non-substituted C.sub.1-20 alkylene or phenylene group, and A is --COO or --SO.sub.3 ]and/or an ampho-ionic group represented by the formula: ##STR2## [wherein each R.sup.2 is the same or different and respectively indicates a C.sub.1-10 alkyl group which optionally has a substituent or a functional group in a chain, and R and A are as defined above] in a molecule and containing a resin having total acid value of 5 to 150.
    Type: Grant
    Filed: December 30, 1994
    Date of Patent: December 26, 1995
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Kazunori Kanda, Yoshifumi Ichinose, Seiji Arimatsu
  • Patent number: 5478692
    Abstract: Proposed is a novel positive-working photoresist composition suitable for use in the fine patterning works in the manufacture of electronic devices and capable of exhibiting excellent performance with high resolution, high sensitivity, wide range of focusing depth, large exposure dose latitude and other characteristics. The photoresist composition is formulated, in addition to the basic ingredients of an alkali-soluble novolac resin as a film-forming agent and photosensitive ingredient such as an ester of naphthoquinone-1,2-diazide sulfonic acid and a polyhydroxy compound, with a limited amount of 4,4'-bis(dialkylamino) benzophenone, e.g., 4,4'-bis(diethylamino) benzophenone, preferably, in combination with a polyhydroxy compound such as 4,6-bis[1-methyl-1-(4-hydroxyphenyl)ethyl]-1,3-dihydroxy phenol.
    Type: Grant
    Filed: November 29, 1994
    Date of Patent: December 26, 1995
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Kousuke Doi, Taku Nakao, Remi Numata, Nobuo Tokutake, Hidekatsu Kohara, Toshimasa Nakayama
  • Patent number: 5476750
    Abstract: The present invention provides methods for producing water insoluble, aqueous alkali soluble novolak resins having a very low level of metal ions and a substantially consistent molecular weight. A method is also provided for producing photoresist composition from such novolak resins and for producing semiconductor devices using such photoresist compositions.
    Type: Grant
    Filed: December 29, 1992
    Date of Patent: December 19, 1995
    Assignee: Hoechst Celanese Corporation
    Inventors: M. Dalil Rahman, Ping-Hung Lu, Daniel P. Aubin, Ralph R. Dammel, Dana L. Durham
  • Patent number: 5468590
    Abstract: A positive resist composition containing a quinone diazide compound and an alkali-soluble resin which contains a resin (A) obtained by a condensation reaction of an aldehyde compound, at least one phenol compound of the formula: ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are independently a hydrogen atom, or a C.sub.1 -C.sub.4 alkyl or alkoxy group, and j is 1 or 2, and at least one compound of the formula: ##STR2## wherein R'.sub.1, R'.sub.2, R'.sub.3, R'.sub.4, R'.sub.5 and R'.sub.6 are independently a hydrogen atom, or a C.sub.1 -C.sub.4 alkyl or alkoxy group, R'.sub.7 is a hydrogen, a C.sub.1 -C.sub.4 alkyl group or an aryl group, and k, m and n are independently 0, 1 or 2 provided that a sum of k, m and n is larger than 2, which composition is excellent in balance among various properties such as a profile, a sensitivity, heat resistance and a depth of focus.
    Type: Grant
    Filed: November 29, 1994
    Date of Patent: November 21, 1995
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kazuhiko Hashimoto, Haruyoshi Osaki, Chinehito Ebina, Kyoko Nagase, Hiroshi Moriuma, Yasunori Uetani
  • Patent number: 5462840
    Abstract: A compound, method of manufacture and method for use of an alternating copolymer having the structure ##STR1## wherein X is independently H, C.sub.1 to C.sub.10 alkyl or alkoxy, primary or secondary amino or halogen, and R is aliphatic, cycloaliphatic, or aliphatic heterocyclic, and wherein the molecular weight ranges from about 1,000 to 50,000.
    Type: Grant
    Filed: March 19, 1991
    Date of Patent: October 31, 1995
    Assignee: Hoechst Celanese Corporation
    Inventor: Richard Vicari
  • Patent number: 5460917
    Abstract: A positive working photosensitive lithographic printing plate comprising a support having thereon a photosensitive layer comprising a positive photosensitive composition, wherein the positive photosensitive composition comprises a mixture of (a) a phenol derivative, (b) a water-soluble and aqueous alkali-soluble resin, and (c) o-quinonediazide or a mixture of a compound capable of forming an acid on exposure and a compound having at least one C--O--C group which is decomposable with an acid, and wherein the phenol derivative is a mixture of a compound represented by the following formula (I) and a compound represented by the following formula (II): ##STR1## wherein X.sup.1, X.sup.2, X.sup.3, X.sup.4, X.sup.5 and X.sup.6 are the same or different and each represents --CH.sub.2 OH or a hydrogen atom, provided that at least three of them are each --CH.sub.2 OH; ##STR2## wherein Y.sup.1, Y.sup.2, Y.sup.3, Y.sup.4, Y.sup.5 and Y.sup.6 are the same or different and each represents --CH.sub.2 OCH.sub.3, --CH.sub.
    Type: Grant
    Filed: August 26, 1994
    Date of Patent: October 24, 1995
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Fumikazu Kobayashi, Kazuyoshi Mizutani, Akira Nagashima
  • Patent number: 5456995
    Abstract: A positive resist composition which comprises, in admixture, a photosensitive 1,2-quinone diazide compound, an alkali-soluble resin to bind ingredients and polyphenol compound to control a dissolution rate in a developer represented by the formula: ##STR1## wherein R is C.sub.1-18 or hydrogen, the composition is sensitive to radiation and has good balance of sensitivity, resolving power and heat resistance.
    Type: Grant
    Filed: April 7, 1994
    Date of Patent: October 10, 1995
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Haruyoshi Ozaki, Fumio Oi, Yasunori Uetani, Makoto Hanabata, Takeshi Hioki
  • Patent number: 5456996
    Abstract: A positive resist composition which comprises, in admixture, a photosensitive 1,2-quinone diazide compound, an alkali-soluble resin to bind ingredients and polyphenol compound to control a dissolution rate in a developer having a molecular weight of not more than 550 and represented by the general formula: ##STR1## wherein a, b, c, d, e, and f are the same or different and a number of 0-3, provided that d+f is not less than 1, and provided that if b, d and f are 1, then at least one of a, c, and e is not 0; R.sub.1, R.sub.2 and R.sub.3 are the same or different and a C.sub.1 -C.sub.18 alkyl group, a C.sub.1 -C.sub.18 alkoxy group, a carboxyl group or a halogen atom; R.sub.4 is a hydrogen atom, a C.sub.1 -C.sub.
    Type: Grant
    Filed: April 7, 1994
    Date of Patent: October 10, 1995
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Haruyoshi Ozaki, Fumio Oi, Yasunori Uetani, Makoto Hanabata, Takeshi Hioki
  • Patent number: 5451484
    Abstract: A positive resist composition comprising a quinonediazide compound and an alkali-soluble resin containing resin (A) obtainable through a condensation reaction of at least one compound represented by the general formula (I): ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 independently of one another each represent a hydrogen atom or an alkyl or alkoxy group having 1-4 carbon atoms and k represents 1 or 2, at least one polyphenol compound represented by the general formula (II): ##STR2## wherein R.sub.4 ' to R.sub.6 ' each represent a hydrogen atom or an alkyl or alkoxy group and n represents 1 or 2, with an aldehyde compound. This positive resist composition is excellent in properties such as profile, resolution, heat resistance, etc.
    Type: Grant
    Filed: May 27, 1993
    Date of Patent: September 19, 1995
    Assignee: Sumitomo Chemical Company, Ltd.
    Inventors: Kyoko Nagase, Haruyoshi Osaki, Hiroshi Moriuma
  • Patent number: 5449584
    Abstract: The present invention provides a positive photo-sensitive resin composition comprising a polybenzoxazole precursor as a base resin, an organic solvent-soluble polymer or its precursor (e.g., a polyamic acid) as a component for imparting improved adhesion, flexibility or heat resistance, and a diazoquinone compound and/or a dihydropyridine compound as a photosensitive agent. This photo-sensitive resin composition can form a pattern of high resolution and further has excellent adhesion and mechanical properties. The present invention further provides three novel diazoquinone compounds as a photo-sensitive agent, which compounds give high resolution, high contrast and thick-film formability when compounded in a positive photo-sensitive resin composition. The present invention furthermore provides a new type positive photo-sensitive resin composition obtained by reacting a polybenzoxazole precursor with a diazoquinone compound as a photo-sensitive agent.
    Type: Grant
    Filed: March 18, 1994
    Date of Patent: September 12, 1995
    Assignee: Sumitomo Bakelite Company, Ltd.
    Inventors: Toshio Banba, Etsu Takeuchi, Toshiro Takeda, Naoshige Takeda, Akira Tokoh
  • Patent number: 5447825
    Abstract: A photosensitive resin composition comprising an alkali-soluble resin, a quinonediazide-type photosensitive compound and a solvent, as the main components, wherein the alkali-soluble resin is a polycondensation product of 1 at least one phenolic compound of the following formula (A) and 2 (a) formaldehyde and (b) at least one ketone or aldehyde of the following formula (B), and the mixing ratio of the formaldehyde (a) to the ketone or aldehyde (b) is within a range of from 1/99 to 99/1 in terms of the molar ratio of (a)/(b): ##STR1## wherein R.sup.1 is a group of the formula R.sup.2,OR.sup.3,COOR.sup.4 or CH.sub.2 COOR.sup.5,wherein R.sup.2 is a C.sub.1-4 alkyl group, each of R.sup.3,R.sup.4 and R.sup.5 which are independent of one another, is a hydrogen atom or a C.sub.1-4 alkyl group, n is an integer of from 0 to 3, provided that when n is 2 or 3, a plurality of R.sup.1 may be the same or different, and each of R.sup.6 and R.sup.7 which are independent of each other, is a hydrogen atom, a C.sub.
    Type: Grant
    Filed: August 31, 1994
    Date of Patent: September 5, 1995
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Mineo Nishi, Koji Nakano, Yoshihiro Takada
  • Patent number: 5446126
    Abstract: A method of removing metal impurities from a resist component, comprising the steps of:(a) dissolving said resist component in a solvent;(b) washing a cation exchange resin with a solution of a quaternary ammonium compound;(c) contacting the prewashed cation exchange resin with the solution of resist component to remove metal impurities from said solution of resist component; and(d) separating said cation exchange resin bearing said metal impurities from said resist component solution.
    Type: Grant
    Filed: September 3, 1991
    Date of Patent: August 29, 1995
    Assignee: OCG Microelectronic Materials, Inc.
    Inventor: Kenji Honda
  • Patent number: 5446125
    Abstract: A method of removing metal impurities from a resist component, comprising the steps of:(a) dissolving said resist component in a solvent;(b) contacting said resist component solution with a cation exchange resin and a chelate resin for a sufficient amount of time to absorb at least a portion of said metal impurities onto said cation exchange and chelate resins; and(c) separating said cation exchange and chelate resins bearing said metal impurities from said resist component solution.
    Type: Grant
    Filed: September 3, 1991
    Date of Patent: August 29, 1995
    Assignee: OCG Microelectronic Materials, Inc.
    Inventors: Kenji Honda, Edward A. Fitzgerald, Lawrence Ferreira
  • Patent number: 5441845
    Abstract: A photosensitive resin composition which is adapted for protecting articles and particularly, electronic parts, therewith comprises a polyimide precursor of the following general formula ##STR1## wherein each X individually represents a tetravalent organic group, each Y individually represents a divalent organic group, R.sup.1, R.sup.2 and R.sup.3 may be the same or different and represent a hydrogen atom or a monovalent organic group having form 1 to 10 carbon atoms, and p, q and m are, respectively, an integer of 1 or over, and a photosensitive diazoquinone compound.
    Type: Grant
    Filed: February 16, 1994
    Date of Patent: August 15, 1995
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Hiroshige Okinoshima, Hideto Kato
  • 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: 5437952
    Abstract: A photosensitive lithographic printing plate comprises a conductive support and provided thereon, a photoconductive layer of a composition comprising a photoconductor and an esterified compound of o-naphtho-quinonediazide sulfonic acid with a phenol resin, the phenol resin being a polycondensation compound of a monovalent phenol with an aldehyde or a ketone, and the content of the o-naphthoquinonediazide sulfonic acid residue being 0.4.times.10.sup.-3 to 3.0.times.10.sup.-3 mole per gram of the photoconductive layer.
    Type: Grant
    Filed: February 26, 1993
    Date of Patent: August 1, 1995
    Assignee: Konica Corporation
    Inventors: Katsura Hirai, Yasuo Kojima, Kiyoshi Goto
  • 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
  • Patent number: 5434031
    Abstract: Disclosed is a positive-working photoresist composition suitable for use in the photolithographic fine patterning work in the manufacture of electronic devices such as VLSIs. The composition comprises, in addition to an alkali-soluble novolac resin as a film-forming ingredient and an esterification product of naphthoquinone-1,2-diazide sulfonic acid as a photosensitive ingredient, a unique additive compound which is an alkyl or aralkyl ester of 2-hydroxy benzoic acid, such as benzyl salicylate, or a phenol compound substituted at least one alkyl group such as 2-tert-butyl-4-methyl phenol. By virtue of the addition of this unique additive, the inventive photoresist composition exhibits an excellent performance of suppressing the standing wave effect in addition to the excellent photosensitivity, resolving power and depth of focusing in the patterning exposure to light as well as good heat resistance of the patterned resist layer.
    Type: Grant
    Filed: November 17, 1993
    Date of Patent: July 18, 1995
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Taku Nakao, Remi Numata, Kousuke Doi, Nobuo Tokutake, Hidekatsu Kohara, Toshimasa Nakayama
  • Patent number: 5432039
    Abstract: A radiation sensitive resin composition for microlens comprising (a) an alkali-soluble resin, (b) a 1,2-quinonediazide compound, (c) a compound having at least 2 epoxy groups in the molecule, (d) a melamine and (e) a trihalomethyltriazine or an onium salt, which composition exhibits high sensitivity, high resolution and high yield of residual film thickness in the formation of a lens pattern and is small in dependency on heating conditions in the preparation of a microlens.
    Type: Grant
    Filed: October 22, 1993
    Date of Patent: July 11, 1995
    Assignee: Japan Synthetic Rubber Co., Ltd.
    Inventors: Tsutomu Shimokawa, Atsufumi Shimada, Masayuki Endo, Nobuo Bessho
  • Patent number: 5429904
    Abstract: A positive resist composition comprising a quinonediazide compound and an alkali-soluble resin containing resin (A) obtainable through a condensation reaction of at least one compound represented by the general formula (I): ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 independently of one another each represent a hydrogen atom or an alkyl or alkoxy group having 1-4 carbon atoms and k represents 1 or 2, at least one polyphenol compound represented by the general formula ( II ): ##STR2## wherein R.sub.4 ' to R.sub.6 ' each represent a hydrogen atom or an alkyl or alkoxy group and n represents 1 or 2, with an aldehyde compound. This positive resist composition is excellent in properties such as profile, resolution, heat resistance, etc.
    Type: Grant
    Filed: May 27, 1993
    Date of Patent: July 4, 1995
    Assignee: Sumitomo Chemical Company, Ltd.
    Inventors: Kyoko Nagase, Haruyoshi Osaki, Kazuhiko Hashimoto, Hiroshi Moriuma
  • Patent number: 5429905
    Abstract: The present invention relates to a positive-working photoresist composition comprising at least one of the 1,2-naphthoquinonediazido-5- sulfonic acid ester of a polyhydroxy compound represented by formula (1) and the 1,2-naphthoquinonediazido-4-sulfonic acid ester of a polyhydroxy compound represented by formula (1): ##STR1## wherein R represents a hydrogen atom, a hydroxy group, a halogen atom, a nitro group, an alkyl group having from 1 to 6 carbon atoms, an aryl group, or an alkenyl group; and R.sub.1 to R.sub.15, which may be the same or different, each represents a hydrogen atom, a hydroxy group, a halogen atom, an alkyl group having from 1 to 6 carbon atoms, an alkoxy group, or a substituted or unsubstituted cycloalkyl group, with the proviso that at least one of R.sub.1 to R.sub.15 is a substituted or unsubstituted cycloalkyl group.
    Type: Grant
    Filed: April 13, 1994
    Date of Patent: July 4, 1995
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Shiro Tan, Yasumasa Kawabe, Tadayoshi Kokubo
  • Patent number: 5427862
    Abstract: An optical glass fiber coated with a protective layer of photocurable polyimide coating which can be prepared from the polymeric condensation product of 6FDA, DMDE, and a photosensitizing moiety. More particularly, the present invention relates to a photocurable polyimide coated glass fiber useful for optic applications.
    Type: Grant
    Filed: September 30, 1991
    Date of Patent: June 27, 1995
    Assignee: Amoco Corporation
    Inventors: David D. Ngo, Paul J. Cahill, John J. Greczek
  • Patent number: 5427888
    Abstract: A positive photosensitive resin composition contains 50 to 95 parts by weight of a resin (a) composed of a high molecular compound (A) having a molecular weight of 300 to 30,000 and an iodine value of 50 to 500 and containing carbon-carbon double bonds and a group represented by the formula (I) ##STR1## wherein R.sub.1 denotes a hydrogen atom, a halogen atom or an alkyl group having 1 to 3 carbon atoms and X denotes a hydrogen atom or a bond, on the proviso that if X denotes the bond, a carbon atom linked to R.sub.1 and a carbon atom linked to a hydrogen atom together form a portion of a main chain of the high molecular compound (A), and a group represented by the formula (II) ##STR2## wherein R.sub.1 and X denote the same as above, and R.sub.2 denotes an alkyl, cycloalkyl or aryl group, and 5 to 50 parts by weight of a compound (b) containing quinone diazide groups.
    Type: Grant
    Filed: August 3, 1993
    Date of Patent: June 27, 1995
    Assignee: Nippon Oil Co., Ltd.
    Inventors: Eiji Yoda, Hitoshi Yuasa, Yutaka Otsuki
  • Patent number: 5426017
    Abstract: Ternary mixtures of C.sub.4 to C.sub.8 alkyl acetate, C.sub.4 to C.sub.8 alkyl alcohol, and water, formulated to have a flash point of above 100.degree. F., are disclosed, particularly for use in edge residue removal processes in the fabrication of integrated circuits and like products.
    Type: Grant
    Filed: March 10, 1993
    Date of Patent: June 20, 1995
    Assignee: Hoechst Celanese Corporation
    Inventor: Donald W. Johnson
  • Patent number: 5424167
    Abstract: A positive type resist composition comprising an alkali-soluble novolac resin, a quinonediazide compound and a compound represented by general formula (I): ##STR1## wherein Y.sub.1 to Y.sub.10 each represent a hydrogen atom, a hydroxyl group or an alkyl group, provided that at least one of Y.sub.1 to Y.sub.10 is a hydroxyl group, and X represents one of the groups represented by the following formulas: ##STR2## wherein R.sub.1 to R.sub.3 independently of one another each represent a hydrogen atom or an alkyl group, provided that, as measured by GPC, the pattern area of the component having a molecular weight, converted to polystyrene, 1,000 or below in the alkali-soluble novolac resin is 25% or less based on the total pattern area of the novolac resin from which the pattern area of the unreacted phenol compound is excepted. This positive type resist composition is excellent in the balance between performances such as sensitivity, resolution, heat resistance and adhesive property.
    Type: Grant
    Filed: February 25, 1993
    Date of Patent: June 13, 1995
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Yasunori Uetani, Hiroshi Moriuma
  • Patent number: 5422221
    Abstract: In a resist composition, a novolak resin including at least one recurring unit of the formula (1): ##STR1## wherein n is an integer of 1 to 4 and m is an integer of 0 to 3, having a weight average molecular weight of 1,000 to 10,000 calculated as polystyrene, and having the hydrogen atom of a hydroxyl group therein replaced by a 1,2-naphthoquinonediazidosulfonyl group in a proportion of 0.03 to 0.27 mol per hydrogen atom serves as an alkali-soluble resin and a photosensitive agent. The composition is uniform in that the photosensitive agent is uniformly incorporated in the novolak resin, and thus forms a uniform resist film. It is a useful positive resist having improved sensitivity, resolution, heat resistance, and film retentivity.
    Type: Grant
    Filed: February 16, 1994
    Date of Patent: June 6, 1995
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Satoshi Okazaki, Mitsuo Umemura, Hiroshi Kanbara, Jun Hatakeyama, Tetsuya Inukai, Kazuhiro Nishikawa
  • Patent number: 5422223
    Abstract: Photosensitive silicon-containing resist compositions comprising hydroxyphenylsilsesquioxanes and siloxanes partially estersified with diazonaphthoquinone sulfonyloxy groups for imageable O.sub.2 RIE barrier films. Methods for forming image patterns on substrates using these photosensitive silicon-containing resist compositions are also provided.
    Type: Grant
    Filed: July 13, 1994
    Date of Patent: June 6, 1995
    Assignee: International Business Machines Corporation
    Inventors: Krishna G. Sachdev, Harbans S. Sachdev, Joel R. Whitaker
  • Patent number: 5422222
    Abstract: A positive-type photosensitive electrodeposition coating composition comprising (A) a photosensitive compound having a molecular weight of not more than 6,000 and containing at least one modified quinonediazidesulfone units represented by the following formula (I) ##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,R.sub.3 represents an alkylene group, a cycloalkylene group or an alkylene ether group, andA represents a carboxylic acid ester linkage, in a molecule and; or a photosensitive compound obtained by reacting a polyfunctional amino compound with o-benzoquinonediazidesulfonic acid chloride or o-naphthoquinonediazidesulfonic acid chloride, and (B) a water-soluble or water-dispersible resin having a salt-forming group.
    Type: Grant
    Filed: May 26, 1994
    Date of Patent: June 6, 1995
    Assignee: Kansai Paint Co., Ltd.
    Inventors: Yuw Akaki, Junichi Higashi, Naozumi Iwasawa
  • Patent number: 5419995
    Abstract: A photoresist comprising a light sensitive component and an alternating copolymer resin formed by condensing a preformed bishydroxymethylated compound and a reactive phenol, in the absence of an aldehyde. Additional useful resins may be formed by further reacting the alternating copolymer with a second reactive phenol in the presence of an aldehyde to form substantially block copolymers. The use of these resins in photoresist formulations leads to improved thermal properties, etch resistance and photospeed.
    Type: Grant
    Filed: May 13, 1993
    Date of Patent: May 30, 1995
    Assignee: Shipley Company Inc.
    Inventor: Anthony Zampini
  • Patent number: 5413896
    Abstract: An i-ray sensitive positive resist composition: which (A) comprises an alkali-soluble novolak resin obtained by subjecting (a) a phenolic mixture of B to 95 mol % of 2,3-xylenol with 95 to 5 mol % of a phenol selected from mono-, di- and tri-methyl phenols other than 2,3-xylenol or (b) a phenolic mixture of 5 to 50 mol % of 8,4-xylenol with 95 to 50 mol % of a phenol selected from mono-, di- and tri-methyl phenols other than 3,4-xylenol to polycondensation together with an aldehyde, and a 1,2-quinonediazide compound, and (B) which has sensitivity to i-ray. There is also provided a method of forming a pattern, which comprises: (1) applying the i-ray sensitive positive resist composition to a wafer to form a photosensitive layer, (2) irradiating the photosensitive layer with i-ray through a predetermined pattern, and (3) developing the pattern with a developer.
    Type: Grant
    Filed: January 17, 1992
    Date of Patent: May 9, 1995
    Assignee: Japan Synthetic Rubber Co., Ltd.
    Inventors: Toru Kajita, Toshiyuki Ota, Yoshiji Yumoto, Takao Miura
  • Patent number: 5413894
    Abstract: A phenolic novolak composition prepared by a process comprising the steps of:(1) reacting a first phenolic monomer comprising a major portion of at least one trifunctional phenolic monomer with a first aldehyde source in the absence of a catalyst at a reaction temperature from about 100.degree. C. to about 200.degree. C. and at a reaction pressure of about 2 to about 15 atmospheres to form a phenolic oligomer having a weight average molecular weight from about 500 to about 2,000, having ortho-ortho bonding of about 55% to about 75% of the methylene bonds between the phenolic moieties; and having a time to clear of less than 125 seconds per micron; wherein the mole ratio of said first aldehyde source to said first phenolic monomer is from about 0.3:1.0 to about 0.55:1.0; and(2) then reacting said oligomer with an optional second phenolic source and a second aldehyde source at a temperature from about 80.degree. C. to about 150.degree. C.
    Type: Grant
    Filed: May 7, 1993
    Date of Patent: May 9, 1995
    Assignee: OCG Microelectronic Materials, Inc.
    Inventors: Joseph J. Sizensky, Thomas R. Sarubbi, Medhat A. Toukhy
  • Patent number: 5413899
    Abstract: A light-sensitive mixture which contains a resinous binder which is insoluble in water but soluble or at least swellable in aqueous-alkaline solutions, and an o-naphthoquinonediazide-sulfonic acid ester, the o-naphthoquinonediazide-sulfonic acid ester being of the formula I ##STR1## in which R is hydrogen or an alkyl or aryl radical andR.sub.1 is hydrogen or a 1,2-naphthoquinone-2-diazide-4-sulfonyl, 1,2-naphthoquinone-2-diazide-5-sulfonyl or 7-methoxy-1,2-naphthoquinone-2-diazide-4-sulfonyl radical,and the number of the identical or different naphthoquinonediazide-sulfonyl radicals, defined as R.sub.1, in the molecule being 1 to 5; is useful in the preparation of light-sensitive resist materials. The resist material produced using the light-sensitive mixture has a high light sensitivity and very good developer resistance to alkaline developers and can be developed without any problems with aqueous, weakly alkaline solutions.
    Type: Grant
    Filed: June 6, 1994
    Date of Patent: May 9, 1995
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Siegfried Scheler, Andreas Elsaesser, Gerhard Buhr, Klaus Bergmann, Wolfgang Zahn
  • Patent number: 5413895
    Abstract: A positive resist composition comprising an alkali-soluble resin containing a novolak resin which is obtained by a condensation reaction of a phenol compound and a carbonyl compound and has an area in a GPC pattern of a range in that a molecular weight as converted to polystyrene is not larger than 900 not exceeding 20% of a whole pattern area excluding the unreacted phenol compound, a quinonediazide compound and a polyphenol compound of the formula: ##STR1## in which R.sub.1 and R.sub.2 are independently a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group or a group: --OCOR.sub.3 in which R.sub.3 is an alkyl group or a phenyl group, x and y are independently an integer of 1 to 3, and m is an integer of 0 to 4, wherein a weight ratio of said polyphenol compound (I) to said alkali-soluble resin is from 3:10 to 5:10, which is excellent in heat resistance, sensitivity, resolution and a depth of focus and leaves no scum after development.
    Type: Grant
    Filed: August 18, 1992
    Date of Patent: May 9, 1995
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Jun Tomioka, Koji Kuwana, Hirotoshi Nakanishi, Yasunori Uetani, Ayako Ida
  • Patent number: 5411836
    Abstract: A positive type photoresist composition contains (a) 100 parts by weight of a resin which is a polymer compound (A) including carbon-carbon double bonds and having a molecular weight of 300 to 30,000 and an iodine value of to 500. To at least a part of the double bonds of the polymer compound (A), a group represented by the formula (I) is introduced ##STR1## wherein R.sup.1 denotes a hydrogen atom, a halogen atom or an alkyl group having 1 to 3 carbon atoms and R.sup.2 denotes an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group or an aryl group, The composition further contains (b) 25 to 100 parts by weight of a compound containing a quinone diazide unit.
    Type: Grant
    Filed: August 8, 1991
    Date of Patent: May 2, 1995
    Assignee: Nippon Oil Co., Ltd.
    Inventors: Eiji Yoda, Haruyoshi Sato, Yukio Yamasita, Hitoshi Yuasa, Yutaka Otsuki
  • Patent number: 5407779
    Abstract: A positive resist composition comprising an alkali-soluble resin and a light-sensitive quinonediazide material containing a quinonediazidesulfonic acid ester of at least one phenol compound represented by the following general formulas: ##STR1## wherein R.sub.1 represents hydrogen, halogen, or the like; R.sub.3 represents alkyl or phenyl; x represents 1-3; Q.sub.1 to Q.sub.12 represent hydrogen, alkyl or phenyl; and Z.sub.1 to Z.sub.5 represent the groups of the following formulas: ##STR2## wherein R.sub.2 is hydrogen, halogen or the like; R.sub.3 is as defined above; y is 1-3; and p is 0 or 1. This positive resist composition is excellent in the balance between properties such as resolution, profile, depth of focus, etc.
    Type: Grant
    Filed: June 4, 1993
    Date of Patent: April 18, 1995
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yasunori Uetani, Jun Tomioka, Hirotoshi Nakanishi
  • Patent number: 5407780
    Abstract: A positive resist composition containing a 1,2-quinone diazide compound and an alkali-soluble resin which constitutes a resin (I) obtainable through a condensation reaction of a phenol mixture containing m-cresol and 2-tert.-butyl-5-methylphenol with an aldehyde., which has well balanced sensitivity, resolution and heat resistance properties.
    Type: Grant
    Filed: May 11, 1994
    Date of Patent: April 18, 1995
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Takeshi Hioki, Seiko Kurio, Yasunori Uetani, Yasunori Doi, Hiroshi Moriuma
  • Patent number: 5407778
    Abstract: A positive resist composition comprising an alkali-soluble resin and a light-sensitive quinonediazide material containing a quinonediazidesulfonic acid diester of at least one member selected from the phenol compounds represented by the following general formulas: ##STR1## wherein R.sub.1 and R.sub.2 each represent hydrogen, halogen, --OCOR.sub.3, alkyl or alkoxy in which R.sub.3 represents alkyl or phenyl, x and y each represent 1, 2 or 3, and R, R.sub.o, R' and R.sub.o ' each represent hydrogen atom, alkyl or phenyl group; wherein the content of said diester is 50% or greater based on the total light-sensitive quinonediazide material. This composition is excellent in the balance between properties such as resolution, profile and depth of focus.
    Type: Grant
    Filed: May 13, 1993
    Date of Patent: April 18, 1995
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yasunori Uetani, Jun Tomioka, Hirotoshi Nakanishi
  • Patent number: 5405720
    Abstract: A radiation-sensitive resin composition comprising a solution of an alkali-soluble resin and a radiation-sensitive compound in a solvent comprising a monooxymonocarboxylic acid ester. This composition has a high storage stability (i.e., a very small amount of fine particles are formed during storage) and is suited for use as a resist for making integrated circuits.
    Type: Grant
    Filed: February 15, 1994
    Date of Patent: April 11, 1995
    Assignee: Japan Synthetic Rubber Co., Ltd.
    Inventors: Yoshihiro Hosaka, Ikuo Nozue, Masashige Takatori, Yoshiyuki Harita
  • Patent number: 5403695
    Abstract: Disclosed herein is a resist for forming patterns, which is greatly sensitive to ultraviolet rays an ionizing radiation, and which can therefore form a high-resolution resist pattern if exposed to ultra violet rays or an unionizing radiation. Hence, the resist is useful in a method of manufacturing semicon ductor devices having high integration densities. The resist comprises tert-butoxycarbonyl methoxypolyhydroxy styrene and an o-quinonediazide compound.
    Type: Grant
    Filed: April 30, 1992
    Date of Patent: April 4, 1995
    Assignee: Kabushiki Kaisha Toshiba
    Inventors: Rumiko Hayase, Yasunobu Onishi, Hirokazu Niki, Naohiko Oyasato, Yoshihito Kobayashi, Shuzi Hayase
  • Patent number: 5403696
    Abstract: A positive resist composition comprising a 1,2-quinone diazide compound and an alkali-soluble resin which comprises a resin (I) obtainable through a condensation reaction of an aldehyde with a phenol mixture containing m-cresol and at least one selected from the group consisting of 2-tert.-butyl-4-methylphenol and 2-tert.-butyl-6-methylphenol, which has well balanced properties.
    Type: Grant
    Filed: April 19, 1993
    Date of Patent: April 4, 1995
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Takeshi Hioki, Seiko Kurio, Yasunori Uetani, Yasunori Doi
  • Patent number: RE35217
    Abstract: An aqueous developer solution contains, as a water-soluble basic compound, a compound of the general formula (I) ##STR1## where R.sup.1 to R.sup.5 are identical or different and are each H, OH, hydroxyalkyl, alkoxy or alkyl.It is suitable for developing positive-working photoresists.
    Type: Grant
    Filed: May 9, 1994
    Date of Patent: April 23, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Reinhold Schwalm, Horst Binder