And Monomeric Processing Ingredient Patents (Class 430/191)
  • Patent number: 5340686
    Abstract: A positive-type photoresist composition is described as including:(1) an alkali-soluble phenol novolak having a degree of dispersion of from 1.5 to 4.0;(2) a 1,2-quinone diazide compound; and(3) from 2 to 30% by weight, based on the above-mentioned novolak, of a low molecular weight compound having a total of from 12 to 50 carbon atoms per molecule and 2 to 8 phenolic hydroxyl groups per molecule. The degree of dispersion is determined from a weight-average molecular weight of the novolak and a number-average molecular weight of the novolak, both the weight-average and number-average molecular weights being obtained by gel penetration chromatography (GPC) defined by using standard polystyrene as a reference, such that the degree of dispersion is a ratio of the weight-average molecular weight to the number average molecular weight.The positive-type photoresist composition of the present invention is excellent in development latitude and has a high sensitivity and a high resolving power.
    Type: Grant
    Filed: December 28, 1993
    Date of Patent: August 23, 1994
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Shinji Sakaguchi, Shiro Tan, Tadayoshi Kokubo
  • Patent number: 5340687
    Abstract: An alkali-soluble binder resin made by a condensation reaction of hydroxy styrene moiety having formulae (I) or (II): ##STR1## wherein x is an integer from 2 to 300; with a monomethylolated phenolic compound having a formula (III): ##STR2## wherein R.sub.1 and R.sub.2 are individually selected from the group consisting of lower alkyl group having 1-4 carbon atoms, lower alkoxy group having 1-4 carbon atoms, amino group, and carboxylic acid group; wherein R.sub.3 and R.sub.4 are individually selected from the group consisting of hydrogen, lower alkyl group having 1-4 carbon atoms, lower alkoxy groups having 1-4 carbon atoms, an amino group, and a carboxylic group; and wherein the mole ratio of the hydroxy styrene moiety to the monomethylolated phenolic compound is from about 1:10 to about 10:1.
    Type: Grant
    Filed: May 6, 1992
    Date of Patent: August 23, 1994
    Assignee: OCG Microelectronic Materials, Inc.
    Inventor: Kenji Honda
  • Patent number: 5340688
    Abstract: Disclosed is a novel positive type photoresist composition comprising a 1,2-naphthoquinonediazido-5-(and/or -4-)sulfonic ester of a member selected from the group consisting of the polyhydroxy compounds represented by the following formula (I), (II) or (III) and an alkali-soluble resin: ##STR1## wherein the variables of Formula I are defined in the specification; ##STR2## wherein the variables of Formula II are defined in the specification; ##STR3## wherein the variables of Formula III are defined in the specification.
    Type: Grant
    Filed: February 10, 1993
    Date of Patent: August 23, 1994
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Yasumasa Kawabe, Toshiaki Aoai, Tadayoshi Kokubo
  • Patent number: 5340683
    Abstract: A PS plate comprises a surface-grained and anodized aluminum plate provided thereon with a light-sensitive layer of a composition comprising a light-sensitive substance and an alkali-soluble resin wherein the light-sensitive substance is a 1,2-naphthoquinonediazide-5- (or -4-) sulfonic acid ester of a polyhydroxy compound of formula (I): ##STR1## wherein substituents R.sub.1 to R.sub.4 may be same or different and each represents a hydrogen atom, a hydroxyl group, a halogen atom, an alkyl group, an alkoxy group or an alkenyl group; R.sub.5 and R.sub.6 each represents a hydrogen atom, an alkyl group or a group: ##STR2## a and c each represents 0-1 and b represents 0-4. The PS plate permits the complete removal of any pasting mark and has a high development latitude.
    Type: Grant
    Filed: July 7, 1993
    Date of Patent: August 23, 1994
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Syunichi Kondo, Akira Nagashima, Yasumasa Kawabe
  • Patent number: 5340682
    Abstract: A positive-working radiation-sensitive mixture is disclosed which contains as essential constituents:a) an .alpha.-carbonyl-.alpha.-sulfonyl-diazomethane, which forms a strong acid on irradiation, of the general formula I ##STR1## in which R.sup.1 and R.sup.2, independently of one another, denote an alkyl-, cycloalkyl-, aryl- or heteroaryl radicalb) a compound having at least one C--O--C or C--O--Si bond which can be cleaved by acid, andc) a water-insoluble binder which is soluble or at least swellable in aqueous-alkaline solutions.The radiation-sensitive mixture according to the invention is notable for a high sensitivity over a wide spectral range. It also exhibits a high thermal stability and does not form any corrosive photoylsis products on exposure to light.
    Type: Grant
    Filed: April 9, 1993
    Date of Patent: August 23, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Georg Pawlowski, Hans-Joachim Merrem, Juergen Lingnau, Ralph Dammel, Horst Roeschert
  • Patent number: 5338652
    Abstract: A novolak resin composition comprising at least one unit of the reaction product of a para-, para-bonded bisphenol having formula (A): ##STR1## wherein R.sub.1 =hydrogen, lower alkyl group having 1-4 carbon atoms, halogen, or lower alkoxy group having 1-4 carbon atoms; whereinR.sub.2 =hydrogen or lower alkyl group having 1-4 carbon atoms; and whereinX is selected from the group consisting of: CH.sub.2, CH(CH.sub.3), C(CH.sub.3).sub.2, O, and S;with a bismethylol monomer selected from a difunctional ortho-, ortho-phenolic bismethylol of Formula (B), a difunctional ortho-, para-phenolic bismethylol of Formula (C): ##STR2## wherein R.sub.3 is selected from CH.sub.3, CH.sub.2 CH.sub.3, Cl, and Br; and whereinR.sub.4 is selected from H and CH.sub.3.
    Type: Grant
    Filed: February 9, 1994
    Date of Patent: August 16, 1994
    Assignee: OCG Microelectronic Marterials, Inc.
    Inventors: Thomas R. Sarubbi, Joseph J. Sizensky
  • Patent number: 5338641
    Abstract: A positive-working radiation-sensitive mixture is disclosed which contains as essential constituents:a) an .alpha.,.alpha.-bis(sulfonyl)diazomethane, which forms a strong acid on irradiation, of the general formula ##STR1## in which R is an optionally substituted alkyl, cycloalkyl, aryl or heteroaryl radical,b) a compound having at least one C--O--C or C--O--Si--bond which can be cleaved by acid, andc) a water-insoluble binder which is soluble or at least swellable in aqueous alkaline solutions.The radiation-sensitive mixture according to the invention is notable for a high sensitivity over a wide spectral range. It also exhibits a high thermal stability and does not form any corrosive photolysis products on exposure to light.
    Type: Grant
    Filed: March 4, 1993
    Date of Patent: August 16, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Georg Pawlowski, Hans-Joachim Merrem, Juergen Lingnau, Ralph Dammel, Horst Roeschert
  • Patent number: 5338643
    Abstract: Disclosed herein is a photosensitive composition comprising:(A) 5 to 60 wt % of an o-quinonediazide compound;(B) 0.05 to 10 wt % of an s-triazine compound(C) 0.01 to 10 wt % of a dye for changing the color tone by the interaction with the photodecomposition product of the said s-triazine compound;(D) 30 to 90 wt % of a novolak resin containing less than 5 wt % of phenols; and(E) 1 to 60 wt % of a vinyl-based polymer having at least a phenolic hydroxyl group.
    Type: Grant
    Filed: December 23, 1992
    Date of Patent: August 16, 1994
    Assignees: Mitsubishi Kasei Corporation, Konica Corporation
    Inventors: Daisuke Kanazawa, Mitsuru Sasaki, Toshiyuki Urano, Youko Yamashita, Shinichi Matsubara
  • Patent number: 5338653
    Abstract: A phenolic novolak resin composition comprising a condensation product of at least one aldehyde source with a phenolic source comprising 5-indanol. Said phenolic novolak resins are used in radiation-sensitive compositions, especially those useful as positive-working photoresists.
    Type: Grant
    Filed: February 9, 1994
    Date of Patent: August 16, 1994
    Assignee: OCG Microelectronic Materials, Inc.
    Inventor: Medhat A. Toukhy
  • Patent number: 5336583
    Abstract: A positive resist composition containing, in admixture, an alkali-soluble resin, a quinone diazide compound and a mixed solvent of ethyl lactate and at least one solvent selected from the group consisting of (a) n-amyl acetate and (b) 2-heptanone in a weight ratio of 5:95 to 80:20, which composition has a good coating properties and provides an improved profile and a large depth of focus.
    Type: Grant
    Filed: December 6, 1993
    Date of Patent: August 9, 1994
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yasunori Uetani, Yasunori Doi, Kazuhiko Hashimoto, Haruyoshi Osaki, Ryotaro Hanawa
  • Patent number: 5334481
    Abstract: Addition of compounds of formula I ##STR1## in which R.sup.1 to R.sup.4 are each hydroxyl or C.sub.1-6 -alkoxy and R.sup.5 to R.sup.10 are each hydrogen or C.sub.1-6 -alkyl,to positive photoresist compositions based on a diazoquinone/novolak resin effectively suppresses stray radiation and halation effects in corresponding photoresist coatings, in particular if these coatings have been applied to highly reflective substrates.
    Type: Grant
    Filed: April 25, 1991
    Date of Patent: August 2, 1994
    Assignee: Ciba-Geigy Corporation
    Inventor: Hans J. Merrem
  • Patent number: 5332650
    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: September 4, 1992
    Date of Patent: July 26, 1994
    Assignee: Japan Synthetic Rubber Co., Ltd.
    Inventors: Makoto Murata, Mikio Yamachika, Yoshiji Yumoto, Takao Miura
  • Patent number: 5332647
    Abstract: A positive-working photosensitive resin composition useful as a photoresist material in the fine patterning work for the manufacture of semiconductor devices is proposed. The composition is excellent in the storage stability and capable of giving a patterned resist layer having good film thickness retention, cross sectional profile of line patterns, resolution and heat resistance. The composition comprises, in addition to a conventional alkali-soluble novolac resin as a film-forming agent and a quinone diazide group containing compound as a photosensitizing agent, a specific isocyanurate compound substituted at each nitrogen atom with a hydroxy- and ter-butyl-substituted benzyl group.
    Type: Grant
    Filed: August 24, 1993
    Date of Patent: July 26, 1994
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hayato Ohno, Nobuo Tokutake, Satoshi Niikura, Hidekatsu Kohara, Toshimasa Nakayama
  • Patent number: 5328806
    Abstract: A radiation-sensitive composition comprising an admixture in a solvent of: at least one alkali-soluble binder resin, at least one photoactive compound and an effective sensitivity enhancing amount of at least one dimeric or trimeric unit formed by the condensation reaction of an aldehyde with sesamol; the amount of said binder resin being about 60 to 95% by weight, the amount 40% of said photoactive component being about 5% to about by weight, based on the total solids content of said radiation-sensitive composition.
    Type: Grant
    Filed: October 12, 1993
    Date of Patent: July 12, 1994
    Assignee: OCG Microelectronic Materials, Inc.
    Inventor: Medhat A. Toukhy
  • Patent number: 5326665
    Abstract: A positive type resist composition comprising an alkali-soluble resin and a quinonediazide compound, wherein the alkali-soluble resin containing resin (A) is obtainable through a condensation reaction with at least one phenol compound represented by the following general formula (I): ##STR1## wherein R.sub.1 to 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 compound represented by the following general formula (II): ##STR2## wherein R.sub.4 represents a hydrogen atom, an alkyl group having 1-4 carbon atoms or a phenyl group, R.sub.5 to R.sub.7 independently of one another each represent a hydrogen atom or an alkyl or alkoxy group having 1-4 carbon atoms and n represents 1 or 2, and an aldehyde compound. This composition is excellent in the balance between performances such as sensitivity, heat resistance and profile, and is free from scum.
    Type: Grant
    Filed: March 1, 1993
    Date of Patent: July 5, 1994
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Haruyoshi Osaki, Hiroshi Moriuma, Yasunori Uetani
  • Patent number: 5324619
    Abstract: A composition, useful for its excellent resolution, sensitivity, development properties, and heat resistance, having an alkali soluble resin and a quinonediazide compound as essential ingredients, and further containing at least one polyhydroxy compound represented by the following formula (I) or (II): ##STR1## wherein R's, which may be the same or different, each represents a hydrogen atom, a halogen atom, a hydroxyl group, an alkyl group, an alkoxy group or --CH.sub.2 N--(--CH.sub.2 COOH).sub.2 ; X represents a --C(.dbd.O)-- group or an --SO.sub.2 -- group; m is an integer of 1 to 3; and n is an integer of 1 to 4.
    Type: Grant
    Filed: March 25, 1992
    Date of Patent: June 28, 1994
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Yasumasa Kawabe, Kazuya Uenishi, Tadayoshi Kokubo
  • Patent number: 5324618
    Abstract: Disclosed is a positive type photoresist composition comprising an alkali-soluble resin, a quinone diazide compound and a compound represented by the following general formula (I): ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 which may be the same or different and in which four groups for each group may be different from each other at the same time, each represents a hydrogen atom, a hydroxyl group, a halogen atom, an alkyl group, an alkoxy group, a nitro group, an alkenyl group, an aryl group, an aralkyl group, an alkoxycarbonyl group, an arylcarbonyl group, an acyloxy group, an acyl group, an aryloxy group or an aralkoxy group; a, b, d and e each represents 0 or an integer 1 to 3; and c represents 0 or 1, with the proviso that a, b, c, d and e satisfy the relationship (a+b+c+d+e.gtoreq.2), at least one of a and d is 1 or more and at least one of b and e is 1 or more.
    Type: Grant
    Filed: December 3, 1992
    Date of Patent: June 28, 1994
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Yasumasa Kawabe, Shiro Tan, Tadayoshi Kokubo
  • Patent number: 5324620
    Abstract: A radiation-sensitive composition dissolved in a solvent comprising:(A) a photoactive compound;(B) an alkali-soluble novolak binder resin made by the condensation reaction of a mixture of phenolic monomers and phenolic dimers with an aldehyde source, said mixture of phenolic monomers and phenolic dimers comprising:(1) 2-25% by weight of said mixture being at least one monofunctinal phenolic monomer;(2) about 98-75% by weight of said mixture comprising a mixture of difunctional phenolic monomers or dimers comprising:(a) about 0.
    Type: Grant
    Filed: July 26, 1993
    Date of Patent: June 28, 1994
    Assignee: OCG Microeletronic Materials, Inc.
    Inventor: Charles E. Ebersole
  • Patent number: 5322757
    Abstract: Improved photoresist compositions having high resolution and high thermal resistance, produced from certain novolak polymers and diazoquinone photosensitizers. The useful novolak polymers are formed from phenolic mixtures including 2,3,5-trimethyl phenol and/or 2,3-dimethyl phenol, and optional amounts of 2,6-dimethyl phenol, o-cresol and p-cresol.
    Type: Grant
    Filed: March 24, 1993
    Date of Patent: June 21, 1994
    Assignee: OCG Microelectronic Materials, Inc.
    Inventor: Charles E. Ebersole
  • Patent number: 5318874
    Abstract: A composition for forming a photosensitive coating is disclosed which includes:(a) a photosensitive agent which is an o-naphthoquinone diazide compound,(b) a polyvinylpyrrolidone compound, and(c) a stannic halide, wherein the o-naphthoquinone diazide compound is present in an amount of 5-50 parts by weight per 100 parts by weight of the polyvinylpyrrolidone compound and the stannic halide is present in an amount of 4-40% based on the weight of the o-naphthoquinone diazide compound.
    Type: Grant
    Filed: March 25, 1992
    Date of Patent: June 7, 1994
    Assignee: Somar Corporation
    Inventors: Shinichi Yamamoto, Masatoshi Tomiki, Naohiko Kiryu, Akiko Yamazaki
  • Patent number: 5318875
    Abstract: A positive photoresist composition includes an alkali-soluble resin, a quinonediazide compound and a compound selected from the group consisting of compounds represented by formulae (I), (II) and (III): ##STR1## wherein R.sub.1 to R.sub.27, which may be the same or different, each represents a hydrogen atom, hydroxyl group, halogen atom, alkyl group, alkoxy group, nitro group, alkenyl group, aryl group, aralkyl group, alkoxycarbonyl group, arylcarbonyl group, acyloxy group, acyl group, aryloxy group or aralkoxy group; ##STR2## wherein R.sub.31 represents an organic group, single bond, ##STR3## R.sub.32 represents a hydrogen atom, monovalent organic group or ##STR4## R.sub.33 to R.sub.37, which may be the same or different, and in which not all four groups for each of R.sub.33 to R.sub.37 may be the same at the same time, each represents a hydrogen atom, hydroxyl group, halogen atom, alkyl group, alkoxy group or alkenyl group, with the proviso that at least one of R.sub.33 to R.sub.
    Type: Grant
    Filed: February 10, 1993
    Date of Patent: June 7, 1994
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Yasumasa Kawabe, Toshiaki Aoai, Tadayoshi Kokubo, Shiro Tan
  • Patent number: 5316884
    Abstract: A phenolic novolak resin composition comprising a condensation product of at least one aldehyde source with a phenolic source comprising 5-indanol. Said phenolic novolak resins are used in radiation-sensitive compositions, especially those useful as positive-working photoresists.
    Type: Grant
    Filed: September 20, 1993
    Date of Patent: May 31, 1994
    Assignee: OCG Microelectronic Materials, Inc.
    Inventor: Medhat A. Toukhy
  • Patent number: 5314783
    Abstract: A photosensitive resin composition comprising (A) an alkaline aqueous solution-soluble novolak resin, (B) a photosensitizer obtained by reacting a polyhydroxy compound with 1,2-naphthoquinone-(2)-diazido-5(or 4)-sulfonyl chloride, and (C) an ultraviolet absorber such as 2-(2'-hydroxy-5'-methylphenyl)-benzotriazole, has a strong absorption against a light of a wavelength of 365 nm and is suitable for producing semiconductor elements, etc.
    Type: Grant
    Filed: November 2, 1992
    Date of Patent: May 24, 1994
    Assignees: Hitachi Chemical Co., Ltd., Hitachi, Ltd.
    Inventors: Shigeru Koibuchi, Asao Isobe, Michiaki Hashimoto
  • Patent number: 5314782
    Abstract: A positive working deep UV sensitive photoresist which provides improved critical dimension stability during prolonged periods of post exposure delay before baking comprises an acid stable polymer which is insoluble in water but normally soluble in an aqueous alkaline medium, a photo acid generator exemplified by the tri-(2,1,4-diazonaphthoquinonesulfonate) ester of 3,5-dinitro-2,6-dimethylol para cresol, and a mixed carbonate ester of tertiary butyl alcohol and a polyhydric phenol which is an acid labile compound which inhibits the dissolution of the normally soluble polymer in said alkaline medium.
    Type: Grant
    Filed: March 5, 1993
    Date of Patent: May 24, 1994
    Assignee: Morton International, Inc.
    Inventors: Richard M. Lazarus, Thomas A. Koes
  • Patent number: 5308743
    Abstract: A positive-type photoresist composition is disclosed, which comprises:(A) an o-quinonediazide compound;(B) an alkali-soluble phenol resin; and(C) at least one compound selected from a group consisting of urea compounds, thiourea compounds and arylamine compounds; A positive-type photoresist composition which comprises:(A) an o-quinonediazide compound;(B) an alkali-soluble phenol resin; and(C) at least one compound selected from a group consisting of urea compounds, thiourea compounds, and arylamine compounds represented by general formulae (I), (II) and (III), respectively, ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, and R.sub.4 each represents a hydrogen atom, an alkyl group, an aryl group, or any two of R.sub.1, R.sub.2, R.sub.3, and R.sub.4 form at least one ring together, ##STR2## wherein R.sub.5, R.sub.6, and R.sub.
    Type: Grant
    Filed: March 6, 1992
    Date of Patent: May 3, 1994
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kesanao Kobayashi, Nobuaki Matsuda
  • Patent number: 5306594
    Abstract: A novolak resin composition comprising at least one unit of the reaction product of a para-, para-bonded bisphenol having formula (A): ##STR1## wherein R.sub.1 =hydrogen, lower alkyl group having 1-4 carbon atoms, halogen, or lower alkoxy group having 1-4 carbon atoms;wherein R.sub.2 =hydrogen or lower alkyl group having 1-4 carbon atoms; andwherein X is selected from the group consisting of: CH.sub.2, CH(CH.sub.3), C(CH.sub.3).sub.2, O, and S;with a bismethylol monomer selected from a difunctional ortho-, ortho-phenolic bismethylol of Formula (B), a difunctional ortho-, para-phenolic bismethylol of Formula (C): ##STR2## wherein R.sub.3 is selected from CH.sub.3, CH.sub.2 CH.sub.3, Cl, and Br; andwherein R.sub.4 is selected from H and CH.sub.3.
    Type: Grant
    Filed: November 4, 1991
    Date of Patent: April 26, 1994
    Assignee: OCG Microelectronic Materials, Inc.
    Inventors: Thomas R. Sarubbi, Joseph J. Sizensky
  • Patent number: 5306595
    Abstract: The present invention relates to a radiation-sensitive composition containing a resinous binder which is insoluble in water, but soluble or at least swellable in aqueous alkaline solutions, at least one radiation-sensitive compound and optionally a crosslinking agent. The radiation-sensitive compound is an ester composed of a) a compound containing 2 to 6 aromatic hydroxyl groups, b) a ring-substituted (o-naphthoquinone 2-diazide)-4-sulfonic acid (diazo compound D.sub.1) and c) an (o-naphthoquinone 2-diazide)-4- or -5-sulfonic acid which is not further substituted (diazo compound D.sub.2) and/or a non-radiation-sensitive organic acid (compound D.sub.0) , where the D.sub.1 :(D.sub.2 and/or D.sub.0) molar ratio is between about 0.1:1 and 30:1.
    Type: Grant
    Filed: April 1, 1992
    Date of Patent: April 26, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Siegfried Scheler, Wolfgang Zahn, Axel Schmitt, Gerhard Buhr
  • Patent number: 5306596
    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 hyaroxyl 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: October 26, 1990
    Date of Patent: April 26, 1994
    Assignee: Nippon Zeon Co., Ltd.
    Inventors: Masayuki Oie, Shoji Kawata, Takamasa Yamada, Shinya Ikeda
  • Patent number: 5302489
    Abstract: A positive working photoresist composition based on a polyimide or polyimide precursor, a photoactivatable acid generator, and an additive compound, preferably an aromatic silanol, capable of promoting dissolution of the photoactivated portion of the resist, while it has no effect on the rest portion of the resist. Also, a method of patterning the photoresist composition.
    Type: Grant
    Filed: October 29, 1991
    Date of Patent: April 12, 1994
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Suisheng J. Shu
  • Patent number: 5302490
    Abstract: The invention relates to radiation sensitive compositions having high uniformity when deposited as thick films. The compositions of the invention comprise a radiation sensitive component and a resin binder blend. The resin binder blend is a mixture of an aliphatic novolak resin component and an aromatic novolak resin component.
    Type: Grant
    Filed: April 1, 1993
    Date of Patent: April 12, 1994
    Assignee: Shipley Company Inc.
    Inventors: Theodore H. Fedynyshyn, Marc Connelly
  • Patent number: 5296330
    Abstract: Positive photoresist compositions comprising, in an organic solvent, at leasta) one alkali-soluble resin,b) one photosensitive quinone diazide,c) one aromatic hydroxy compound of formula I ##STR1## wherein each R is --H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, --OCH.sub.2 C.sub.6 H.sub.5, --OC.sub.6 H.sub.5 or --COOC.sub.1 -C.sub.4 alkyl, and R.sub.1 and R.sub.2 are each independently of the other H, C.sub.1 -C.sub.4 alkyl, --C.sub.6 H.sub.5 or a cycloaliphatic 5- or 6-membered ring, a is an integer from 0 to 4, and m and n are each independently of the other 0, 1 or 2, which compound enhances the photosensitivity and/or the rate of development, and optionallyd) additional customary modifiers,are eminently suitable for making relief structures.
    Type: Grant
    Filed: August 15, 1992
    Date of Patent: March 22, 1994
    Assignees: Ciba-Geigy Corp., OCG Microelectronics Inc.
    Inventors: Reinhard Schulz, Norbert Munzel, Martin Roth, Wilhelm Knobloch
  • Patent number: 5294521
    Abstract: Positive photoresists formulations for producing positive photoresist images having improved thermal stability yet which allow a wide variation in resin to photoactive sensitizer compound without significant changes in photospeed, thermal behavior, contrast or resolution and with virtually no less in unexposed areas of the photoresist and without significant outgassing or popping are provided by employing novel 1,2-diazonaphthoquinone-4- or -5- sulfonate esters of 2,3,4,3',4',5'-hexahydroxybenzophenone with a novel isomeric distribution of esters. The novel isomeric distribution of 1,2-diazonaphthoquinone-4- or -5- sulfonate esters of 2,3,4,3',4',5'-hexahydroxybenzophenone is characterized by two major isomers, together comprising at least about 70% by weight of the photoactive compound, and wherein the least polar isomer comprises only about 40%.
    Type: Grant
    Filed: January 12, 1993
    Date of Patent: March 15, 1994
    Assignee: Hoechst Celanese Corporation
    Inventors: Elaine C. Jacovich, Wells C. Cunningham
  • Patent number: 5290657
    Abstract: A positive resist composition comprising an alkali-soluble resin, a quinone diazide compound and a specific hydroxyl group-containing compound can improve sensitivity without deterioration of heat resistance and film thickness retention.
    Type: Grant
    Filed: August 15, 1991
    Date of Patent: March 1, 1994
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yasunori Uetani, Hirotoshi Nakanishi
  • Patent number: 5290658
    Abstract: A positive photoresist composition is provided, which comprises an alkali-soluble novolak resin and at least one light-sensitive material represented by formula (III), ##STR1## wherein R.sub.27 and R.sub.28 may be the same or different and which represents --OH, ##STR2## R.sub.29 and R.sub.33 may be the same or different and each represents --H, --OH, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aralkyloxy group, a substituted or unsubstituted acyl group, a substituted or unsubstituted acyloxy group, a halogen, a nitro group, a cyano group, ##STR3## R.sub.34 to R.sub.
    Type: Grant
    Filed: April 24, 1992
    Date of Patent: March 1, 1994
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kazuya Uenishi, Yasumasa Kawabe, Tadayoshi Kokubo
  • Patent number: 5288587
    Abstract: A positive resist composition which comprises a 1,2-quinone diazide compound and an alkali-soluble resin containing a polyphenol compound (I) of the general formula: ##STR1## wherein R is a C.sub.1 -C.sub.5 alkyl group or a C.sub.1 -C.sub.5 alkoxy group, and n is a number of 0 to 3, which has good sensitivity, improved resolution and heat resistance.
    Type: Grant
    Filed: March 31, 1993
    Date of Patent: February 22, 1994
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Haruyoshi Osaki, Yasunori Uetani
  • Patent number: 5288588
    Abstract: A positive photosensitive polyimide resin composition which comprises 100 parts by weight of an organic solvent-soluble polyimide resin and 1-100 parts by weight of an .omicron.-quinonediazide compound, said polyimide resin being composed of the repeating units represented by formulas [I] and [II] below ##STR1## (where R.sub.1 is a divalent organic group to constitute a diamine which has one or more groups of at least one kind selected from the group consisting of phenolic hydroxyl group, carboxyl group, thiophenol group, and sulfonic group; R.sub.3 is a divalent organic group having no phenolic hydroxyl group, carboxyl group, thiophenol group, and sulfonic group; and R.sub.2 and R.sub.4 each are a tetravalent organic group constituting a-tetracarboxylic acid and a derivative thereof when R.sub.1 has one or more groups of at least one kind selected from the group consisting of carboxyl group and sulfonic group and has no phenolic hydroxyl group and thiophenol group, or R.sub.2 and R.sub.
    Type: Grant
    Filed: November 30, 1992
    Date of Patent: February 22, 1994
    Assignee: Nissan Chemical Industries Ltd.
    Inventors: Masahiko Yukawa, Toyohiko Abe, Noriaki Kohtoh
  • Patent number: 5286609
    Abstract: A negative resist pattern is formed using a resist containing a diazoquinone sensitizer. An imagewise exposed area of a layer of the resist is subjected to heat treatment with a water-containing heating medium in the presence of a carboxyl-inactivating agent. The entire surface of the layer is exposed to radiation. The thus-exposed surface is then treated with an alkaline developer solution. An apparatus suitable for use in the practice of the above process is also disclosed.
    Type: Grant
    Filed: January 14, 1992
    Date of Patent: February 15, 1994
    Assignee: Yamatoya & Co., Ltd.
    Inventor: Iwao Numakura
  • Patent number: 5283324
    Abstract: A radiation sensitive compound prepared by reacting a phenol compound with a quinone diazide sulfonyl halide in a mixture of a solvent having a relative dielectric constant of not larger than 10 and a solvent having a relative dielectric constant of at least 15, which compound is less colored and gives a positive resist composition having a good resolution.
    Type: Grant
    Filed: April 17, 1992
    Date of Patent: February 1, 1994
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Jun Tomioka, Koji Kuwana, Hirotoshi Nakanishi, Hiroshi Takagaki, Yasunori Doi, Yasunori Uetani, Ryotaro Hanawa
  • Patent number: 5283155
    Abstract: A positive resist composition which comprises an alkali-soluble resin and, as a sensitizer, a quinone diazide sulfonic acid ester of a phenol compound of the formula: ##STR1## wherein Y.sub.1, Y.sub.2, Z.sub.1, Z.sub.2, Z.sub.3, Z.sub.4, Z.sub.5, Z.sub.6 and Z.sub.7 are independently a hydrogen atom, a hydroxyl group, a C.sub.1 -C.sub.4 alkyl group which may be substituted with a halogen atom, provided that at least one of Y.sub.1 and Y.sub.2 is a hydroxyl group, and at least two of Z.sub.1 to Z.sub.7 are hydroxyl groups, and R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are independently a hydrogen atom, a C.sub.1 -C.sub.10 alkyl group, a C.sub.1 -C.sub.4 alkenyl group, a cycloalkyl group or an aryl group, which composition has a high .gamma.-value.
    Type: Grant
    Filed: June 11, 1991
    Date of Patent: February 1, 1994
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yasunori Uetani, Hirotoshi Nakanishi, Yasunori Doi
  • Patent number: 5279918
    Abstract: A photoresist composition useful for the preparation of semiconductors and to be irradiated by light with a wavelength of from 330 to 450 nm, which comprises (1) an alkali-soluble resin, (2) a quinone-diazide type photosensitive compound and (3) a solvent, wherein(a) said quinone-diazide type photosensitive compound is composed mainly of a quinone-diazide sulfonate of a novolac resin produced by polycondensation of at least one phenolic compound of the following formula (A1) or (A2) and at least one ketone or aldehyde derivative of the following formula (B),(b) the weight-average molecular weight (the analytical value calculated as polystyrene by gel permeation chromatography) of said novolac resin is from 400 to 2,000 in the case of the novolac resin derived from the phenolic compound of the formula (A1) and from 600 to 2,200 in the case of the novolac resin derived from the phenolic compound of the formula (A2), and(c) the esterification ratio of said quinone-diazide sulfonate (the number of quinone-diazide
    Type: Grant
    Filed: April 30, 1991
    Date of Patent: January 18, 1994
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Mineo Nishi, Koji Nakano, Tadashi Kusumoto, Keisuke Nakano, Yoshihiro Takada
  • Patent number: 5279917
    Abstract: A light-sensitive composition comprises a light-sensitive compound, an alkali soluble resin and a fluorine-containing surfactant. The surfactant is a copolymer of a (poyoxyalkylene)acrylate or (polyoxyalkylene)methacrylate with an acrylate or methacrylate having a fluorine-containing aliphatic group. The copolymer has a weight average molecular weight of 1000 to 6000 and contains the acrylate or methacrylate in an amount of 10 to 25% by weight. The fluorine-containing aliphatic group has 6 to 20 carbon atoms and 30% or more by weight of fluorine atoms.
    Type: Grant
    Filed: May 4, 1992
    Date of Patent: January 18, 1994
    Assignee: Konica Corporation
    Inventors: Yutaka Adachi, Hideyuki Nakai, Takeshi Tanaka
  • Patent number: 5279922
    Abstract: A light-sensitive coating liquid, comprising, as an organic solvent, at least one substance represented by the formulae (I) to (III) shown below: ##STR1## wherein R.sub.1 represents an alkyl group having 1 to 4 carbon atoms, R.sub.2 to R.sub.7 each represent hydrogen atom or an alkyl group having 1 to 3 carbon atoms, with the proviso that at least one of R.sub.2 to R.sub.7 is an alkyl group. The light-sensitive coating liquid of this invention is improved in odor, low in toxicity and yet excellent in storability, and is also suitable for preparation of a light-sensitive lithographic printing plate improved in press life and dye remaining.
    Type: Grant
    Filed: March 4, 1992
    Date of Patent: January 18, 1994
    Assignees: Konica Corporation, Mitsubishi Kasei Corporation
    Inventors: Yutaka Adachi, Kiyoshi Goto, Koji Fukazawa, Kunitaka Naito, Masaaki Tsuchiyama
  • Patent number: 5278021
    Abstract: A radiation sensitive mixture comprising an alkali-soluble binder resin and at least one photoactive compound comprising a compound of formula (I): ##STR1## wherein each R is individually selected from hydrogen and a lower alkyl group having 1 to 4 carbon atoms; n is either 0, 1, or 2; and D is selected from the group consisting of hydrogen or o-naphthoquinone diazide sulfonyl group; with the proviso that at least two D's are o-naphthoquinone diazide sulfonyl groups, and wherein the amount of said binder resin is about 70 to 95% by weight and the amount of photoactive compound being from about 5 to about 30% be weight, based on the total solids content of said content of said raditional-sensitive mixture.
    Type: Grant
    Filed: April 5, 1993
    Date of Patent: January 11, 1994
    Assignee: OCG Microelectronic Materials, Inc.
    Inventors: Alfred T. Jeffries, III, Medhat A. Toukhy
  • Patent number: 5278022
    Abstract: A polymeric compound is derived from a polyhydric material and has pendant sulphonate groups of the general formula ##STR1## where X is an aliphatic, aromatic, carbocylic or heterocyclic group; Y is hydrogen, halogen or an alkyl, aryl, alkoxy, aryloxy or aralkyl group, CO.sub. --Z.sup.+, CO.sub.2 R or SO.sub.3 -Z.sup.+ ; Z.sup.+ is a cationic counter ion and R is hydrogen, alkyl, alkylene, aryl or aralkyl group.
    Type: Grant
    Filed: March 18, 1992
    Date of Patent: January 11, 1994
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: John R. Wade, Robert A. W. Johnstone
  • Patent number: 5275909
    Abstract: A radiation-sensitive composition comprising an admixture in a solvent of: at least one alkali-soluble binder resin, at least one photoactive compound and an effective absorbance increasing amount of BLANKOPHOR FBW actinic dye; the amount of said binder resin being about 60 to 95% by weight, the amount of said photoactive component being about 5% to about 40% by weight, based on the total solids content of said radiation-sensitive composition.
    Type: Grant
    Filed: June 1, 1992
    Date of Patent: January 4, 1994
    Assignee: OCG Microelectronic Materials, Inc.
    Inventors: Tripunithura V. Jayaraman, David J. Brzozowy
  • Patent number: 5275908
    Abstract: A positive-working radiation-sensitive mixture and recording material are disclosed. The mixture contains, as essential constituents, a 1,2-quinone diazide and/or a combination of a compound which forms strong acid on exposure to actinic radiation and a compound containing at least one cleavable C--O--C bond and a polymeric binder containing repeating units of formula I ##STR1## in which R.sub.1 is a hydrogen or halogen atom, or a cyanide or an alkyl group, R.sub.2, R.sub.3 are identical or different and are hydrogen, or alkyl or aryl groups, R.sub.4, R.sub.5 are identical or different and are and R.sub.6 hydrogen or halogen atoms, or alkyl, alkoxy or aryl groups, X represents the atoms necessary to complete a monocyclic or polycyclic carbocyclic aromatic ring system, and is 1, 2 or 3. The mixture yields lithographic plates having high print runs which can be thermally post-cured and which have good resistance to chemicals. The mixture also produces photoresists having good heat resistance.
    Type: Grant
    Filed: January 28, 1991
    Date of Patent: January 4, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Andreas Elsaesser, Dieter Mohr
  • Patent number: 5275911
    Abstract: A radiation-sensitive composition comprising an admixture in a solvent of: at least one alkali-soluble binder resin, at least one photoactive compound and an effective sensitivity enhancing amount of at least one dimeric or trimeric unit formed by the condensation reaction of an aldehyde with sesamol; the amount of said binder resin being about 60 to 95% by weight, the amount of said photoactive component being about 5% to about 40% by weight, based on the total solids content of said radiation-sensitive composition.
    Type: Grant
    Filed: February 1, 1993
    Date of Patent: January 4, 1994
    Assignee: OCG Microelectronic Materials, Inc.
    Inventor: Medhat A. Toukhy
  • Patent number: 5275910
    Abstract: A positive radiation-sensitive resist composition comprising an alkali-soluble resin, a radiation-sensitive ingredient and a phenol 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, an alkyl group or an alkoxy group and n represents 1, 2 or 3.
    Type: Grant
    Filed: October 14, 1992
    Date of Patent: January 4, 1994
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Hiroshi Moriuma, Hirotoshi Nakanishi, Yasunori Uetani
  • Patent number: 5273856
    Abstract: Positive photoresist compositions which comprise an alkali soluble resin material, a diazoquinone dissolution inhibitor which decompose on exposure to mid and near UV radiation, and a sulfonic acid ester of an imide or oxime which does not absorb such mid or near UV radiation. Resist images of high contrast are formed.
    Type: Grant
    Filed: October 31, 1990
    Date of Patent: December 28, 1993
    Assignee: International Business Machines Corporation
    Inventors: Christopher F. Lyons, Stanley E. Perreault, Gary T. Spinillo, Robert L. Wood
  • Patent number: 5272036
    Abstract: Disclosed is a pattern forming contrast enhanced material comprising (a) a water soluble photosensitive compound selected from the group consisting of a water soluble aliphatic photosensitive compound (excluding ring compounds) having one or more of the group expressed by the formula (I), an aliphatic photosensitive quaternary ammonium salt having one or more of the group expressed by the formula (I), an aromatic photosensitive quaternary ammonium salt having one or more of the group expressed by the formula (I), and a photosensitive pyridinium salt having one or more of the group expressed by the formula (I), (b) a water soluble resin and (c) water and a pattern forming method using the same. ##STR1## According to the present invention, this material is used as a contrast enhanced layer in the exposure effected by deep ultraviolet ray such as an excimer laser beam to form a good fine pattern of a submicron order.
    Type: Grant
    Filed: March 27, 1992
    Date of Patent: December 21, 1993
    Assignees: Matsushita Electronic Industrial Co., Ltd., Wako Pure Chemical Industries, Ltd.
    Inventors: Yoshiyuki Tani, Masayuki Endo, Kazufumi Ogawa, Fumiyoshi Urano, Masaaki Nakahata