Polymeric Quinone Diazide Patents (Class 430/190)
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Patent number: 5368977Abstract: A positive type photosensitive resin composition contains (a) a quinone diazido phenolic resin represented by the formula: ##STR1## wherein R.sup.1 is an alkyl group having 1 to 4 carbon atoms, R.sup.2 is a bivalent hydrocarbon residue having 5 to 16 carbon atoms provided that groups bound to R.sup.2 do not bind with the same carbon atom of R.sup.2, D.sup.1, D.sup.2 and D.sup.3 and are the same or different groups and each represent a hydrogen atom or a quinone diazido unit represented by ##STR2## provided that a molar ratio of the hydrogen atom to the quinone diazido unit is 0 to 10, m is a number of 0 to 10, n is a number of 1 or 2, and l.sub.1, l.sub.2 and l.sub.3 are the same or different numbers and each represent a number of 1 to 3; and (b) an alkali-soluble resin.Type: GrantFiled: March 19, 1993Date of Patent: November 29, 1994Assignee: Nippon Oil Co. Ltd.Inventors: Eiji Yoda, Hitoshi Yuasa, Yutaka Otsuki
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Patent number: 5344740Abstract: A positive-type photosensitive electrodeposition coating composition comprising(A) a resin component containing in a molecule at least one unit selected from the group consisting of an ortho-benzoquinonediazidesulfone unit represented by the general formula ##STR1## an ortho-naphthoquinonediazidesulfone unit represented by the general formula ##STR2## as a photosensitive group, and an anion-forming group; and (B) at least one of the specified particular nitrogen-containing compounds. The composition is useful for the production of a circuit plate.Type: GrantFiled: May 4, 1992Date of Patent: September 6, 1994Assignee: Kansai Paint Co., Ltd.Inventors: Naozumi Iwasawa, Junichi Higashi, Shinsuke Onishi
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Patent number: 5338643Abstract: 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: GrantFiled: December 23, 1992Date of Patent: August 16, 1994Assignees: Mitsubishi Kasei Corporation, Konica CorporationInventors: Daisuke Kanazawa, Mitsuru Sasaki, Toshiyuki Urano, Youko Yamashita, Shinichi Matsubara
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Patent number: 5326826Abstract: Radiation-sensitive polymers, a mixture containing these radiation-sensitive polymers as binder, and a process for the preparation of the radiation-sensitive polymer binders are disclosed. A positive radiation-sensitive recording material containing the radiation-sensitive polymer is also disclosed.Type: GrantFiled: February 26, 1992Date of Patent: July 5, 1994Assignee: Hoechst AktiengesellschaftInventors: Horst Roeschert, Hans-Joachim Merrem, Georg Pawlowski, Juergen Fuchs, Ralph Dammel
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Patent number: 5314782Abstract: 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: GrantFiled: March 5, 1993Date of Patent: May 24, 1994Assignee: Morton International, Inc.Inventors: Richard M. Lazarus, Thomas A. Koes
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Patent number: 5306596Abstract: 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: GrantFiled: October 26, 1990Date of Patent: April 26, 1994Assignee: Nippon Zeon Co., Ltd.Inventors: Masayuki Oie, Shoji Kawata, Takamasa Yamada, Shinya Ikeda
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Patent number: 5306595Abstract: 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: GrantFiled: April 1, 1992Date of Patent: April 26, 1994Assignee: Hoechst AktiengesellschaftInventors: Siegfried Scheler, Wolfgang Zahn, Axel Schmitt, Gerhard Buhr
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Patent number: 5302489Abstract: 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: GrantFiled: October 29, 1991Date of Patent: April 12, 1994Assignee: E. I. Du Pont de Nemours and CompanyInventor: Suisheng J. Shu
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Patent number: 5302488Abstract: A radiation-sensitive polymer and a mixture containing this radiation-sensitive polymer as a binder are disclosed. A process for the preparation of the radiation-sensitive polymer binder and a positive-working radiation-sensitive recording material which is prepared using the radiation-sensitive mixture are also disclosed.Type: GrantFiled: February 26, 1992Date of Patent: April 12, 1994Assignee: Hoechst AktiengesellschaftInventors: Horst Roeschert, Hans-Joachim Merrem, Georg Pawlowski, Juergen Fuchs, Ralph Dammel
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Patent number: 5281508Abstract: A positive-working photoresist composition suitable for fine patterning in the manufacture of semiconductor devices, e.g., VLSIs, with high fidelity is proposed. The composition comprises 100 parts by weight of a cresol novolac resin and 25-60 parts by weight of a naphthoquinone diazide sulfonic acid ester as the photosensitive component while the cresol novolac resin component is prepared from a mixture of cresol isomers composed of 35-43% of m-cresol and 65-57% of p-cresol with substantial absence of o-cresol or composed of 35-43% of m-cresol, 65-57% of p-cresol and 1% or less of o-cresol.Type: GrantFiled: August 21, 1992Date of Patent: January 25, 1994Assignee: Tokyo Ohka Kogyo Co., Ltd.Inventors: Hidekatsu Kohara, Hatsuyuki Tanaka, Masanori Miyabe, Yoshiaki Arai, Shingo Asaumi, Toshimasa Nakayama, Akira Yokota, Hisashi Nakane
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Patent number: 5279918Abstract: 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-diazideType: GrantFiled: April 30, 1991Date of Patent: January 18, 1994Assignee: Mitsubishi Kasei CorporationInventors: Mineo Nishi, Koji Nakano, Tadashi Kusumoto, Keisuke Nakano, Yoshihiro Takada
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Patent number: 5278022Abstract: 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: GrantFiled: March 18, 1992Date of Patent: January 11, 1994Assignee: E. I. Du Pont de Nemours and CompanyInventors: John R. Wade, Robert A. W. Johnstone
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Patent number: 5275921Abstract: In a pattern forming process using a chemical amplification type resist, a good pattern with high contrast between exposed portions and non-exposed portions due to photobleach of a dye and a large process latitude can be obtained by adding a dye such as Sudan Orange, or a dye having a reducing absorption by exposure to light such as naphthoquinonediazide sulfonic acid ester to a chemical amplification type resist for ultraviolet rays, particularly i-line of 365 nm or ultraviolet rays of 365 nm or less.Type: GrantFiled: March 21, 1991Date of Patent: January 4, 1994Assignee: Matsushita Electric Industrial Co., Ltd.Inventors: Taichi Koizumi, Yoshiyuki Tani, Masaru Sasago
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Patent number: 5268252Abstract: The invention relates to a radiation-sensitive ester which is the condensation product of (a) a compound containing 2 to 6 aromatic hydroxyl groups, (b) a ring-substituted (o-naphthoquinone 2-diazide)-4-sulfonic acid (compound D.sub.1 and (c) an (o-naphthoquinone 2-diazide)-4- or -5-sulfonic acid which is not further substituted (compound D.sub.2) and/or a non-radiation-sensitive organic acid (compound D.sub.0), where the (b):(c) molar ratio is between 0.1:1 and 39:1.Type: GrantFiled: April 1, 1992Date of Patent: December 7, 1993Assignee: Hoechst AktiengesellschaftInventors: Siegfried Scheler, Wolfgang Zahn, Axel Schmitt, Gerhard Buhr
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Patent number: 5260162Abstract: A photosensitizer composition comprising a diazo fluorinated ester containing the hexafluoroisopropylidene group, said photosensitizer selected from hexafluoro-bis-phenols having the following formula: ##STR1## where R is selected from hydrogen, methyl, ethyl and phenyl; and bis-hexafluoroethers having the following formula: ##STR2## wherein R' is selected from hydrogen, methyl, ethyl and phenyl.Type: GrantFiled: December 17, 1990Date of Patent: November 9, 1993Inventors: Dinesh N. Khanna, Robert E. Potvin
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Patent number: 5254432Abstract: The present invention relates to a photosensitive composition comprising an o-quinonediazide compound and a polyurethane resin having a phosphonic acid group, a phosphoric acid group or its ester group. The photosensitive composition of the present invention provides an excellent adhesion to the support, an excellent developability with an aqueous alkali developer, and a high printing durability.Type: GrantFiled: April 26, 1990Date of Patent: October 19, 1993Assignee: Fuji Photo Film Co., Ltd.Inventor: Toshiaki Aoai
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Patent number: 5248582Abstract: A positive type photoresist composition which comprises an alkali soluble novolak resin and at least one light-sensitive material represented by the following general formulae (I) to (IV) to provide a resist pattern with high resolution, high reproduction fidelity, desirable sectional shape, wide latitude of development, high heat resistance and high storage stability: ##STR1## (wherein X represents --CO--, or --SO.sub.2 --; p represents an integer from 2 to 4; R's may be the same or different, each being --H, --OH, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted acyl group, a substituted or unsubstituted acyloxy group, ##STR2## provided that R always contains at least one of ##STR3## ; R.sub.Type: GrantFiled: December 8, 1992Date of Patent: September 28, 1993Assignee: Fuji Photo Film Co., Ltd.Inventors: Kazuya Uenishi, Shinji Sakaguchi, Tadayoshi Kokubo
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Patent number: 5242780Abstract: An electrophoretic positive working photosensitive composition for producing a photoresist pattern on metal base plate comprises a photosensitive compound, in which a photosensitive quinone diazide group is grafted on a polyester, and an acrylic copolymer containing carboxyl group, the composition forms a smooth photoresist film on the plate and has a good adhesion to the surface that no pinehole is found.Type: GrantFiled: October 18, 1991Date of Patent: September 7, 1993Assignee: Industrial Technology Research InstituteInventors: Hsien-Kuang Lin, Jim-Chyuan Shieh, Dhei-Jhai Lin
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Patent number: 5238775Abstract: A radiation-sensitive resin composition containing an alkali-soluble resin, comprising a polyhydroxy compound having the following formula: ##STR1## or a quinonediazidesulfonate of the polyhydroxy compound. The radiation-sensitive resin composition is suitable for use as a positive type photoresist which has such excellent developability as to inhibit effectively the generation of scum in the formation of a photoresist pattern, has high sensitivity and is excellent in heat resistance and remained thickness ratio upon development.Type: GrantFiled: February 19, 1991Date of Patent: August 24, 1993Assignee: Japan Synthetic Rubber Co., Ltd.Inventors: Toru Kajita, Takao Miura, Yoshiji Yumoto, Chozo Okuda
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Patent number: 5238771Abstract: There are disclosed a photosensitive composition which comprises:(1) an o-naphtoquinonediazide compound;(2) an alkali soluble resin; and(3) any one selected from the groups consisting of:(a) an ester compound of a polyoxyalkylene sorbitol fatty acid and/or an ether compound of the fatty acid,(b) an alkylene oxide adduct of castor oil, hardened castor oil, lanolin alcohol, beeswax, phytosterol or phytostanol, and(c) at least one activator selected from the group consisting of polyoxypropylene alkyl ethers, polyoxypropylene alkylphenyl ethers and polyoxypropylene alkyl esters;.and a photosensitive lithographic printing plate which comprises a support; and a photosensitive layer formed by applying the above photosensitive composition.Type: GrantFiled: October 19, 1992Date of Patent: August 24, 1993Assignees: Konica Corporation, Mitsubishi Kasei CorporationInventors: Kiyoshi Goto, Hideyuki Nakai, Hiroshi Tomiyasu, Yoshiko Kobayashi
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Patent number: 5238773Abstract: A composition containing an organosilicon material having terminal quinone groups, and a phenolic-novolak polymer, and use thereof in photolithography.Type: GrantFiled: June 8, 1992Date of Patent: August 24, 1993Assignee: International Business Machines CorporationInventors: Edward D. Babich, Donis G. Flagello, Michael Hatzakis, Jurij R. Paraszczak, Jane M. Shaw, David F. Witman
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Patent number: 5229245Abstract: A positively working photosensitive composition is disclosed useful for making positively working lithographic printing plates of exceptional wear, printing and solvent-resistant characteristics. The positively working photosensitive composition essentially contains a .beta.-dicarbonyl group and a quinone diazide group.Type: GrantFiled: July 26, 1991Date of Patent: July 20, 1993Assignee: Industrial Technology Research InstituteInventors: Dhei-Jhai Lin, Hsien-Kuang Lin, Jim-Chyuan Shieh
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Patent number: 5227473Abstract: A quinone diazide of formula (I) or formula (II):(S)l--(L.sup.1)m=-(Q).sub.n (I)--(L.sup.2 (-S))o-(L.sup.3 (--Q))p- (II)wherein S is a light absorbing portion having an absorption coefficient of greater than 1000 in wavelengths longer than 360 nm; Q is a quinone diazide residue; L.sup.1, L.sup.2 and L.sup.3 are connecting groups connecting S and Q, provided, however, that L.sup.1, L.sup.2 and L.sup.3 do not conjugate S and Q; l, m, n, o and p are integers; andwherein the emission intensity of the compound of formulas (I) and (II) is smaller than the emission intensity of the chromophoric group alone. Also disclosed is a light sensitive composition comprising an alkali soluble resin and the above quinone diazide compound. The quinone diazide compound of the present invention have spectral sensitization with respect to visible light and are useful in visible light projection plates and as visible laser sensing materials.Type: GrantFiled: May 10, 1991Date of Patent: July 13, 1993Assignee: Fuji Photo Film Co., Ltd.Inventors: Kouichi Kawamura, Satoshi Takita
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Patent number: 5225311Abstract: A positive photoresist composition is disclosed, comprising (a) from 50 to 99 parts by weight of a polyhydric phenol compound which is a condensation product between a mixed phenol comprising o-cresol and at least one of 2,5-dimethylphenol and 3,5-dimethylphenol at a molar ratio of from 95/5 to 5/95 and an aldehyde and (b) from 1 to 50 parts by weight of a quinone diazide compound. The composition is excellent in sensitivity, resolving power, heat resistance, and resistance to dry etching.Type: GrantFiled: April 5, 1991Date of Patent: July 6, 1993Assignee: Mitsubishi Petrochemical Co., Ltd.Inventors: Toshitomo Nakano, Masumi Kada
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Patent number: 5223373Abstract: Disclosed is a photosensitive quinone diazide compound for the preparation of a two component positive working photosensitive electrodeposition composition. As the photosensitive group is grafted on a polyurethane, the photosensitive compound thus synthesized has good flexibility and good compatability with acrylic resin. The electrodeposition composition also has good adhesion to the metal base plate when it is coated thereon by electrodeposition means.Type: GrantFiled: April 29, 1991Date of Patent: June 29, 1993Assignee: Industrial Technology Research InstituteInventors: Hsien-Kuang Lin, Jim-Chyuan Shieh
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Patent number: 5178986Abstract: A radiation sensitive oligomeric compound is described as the photoactive component with a base soluble phenolic matrix resin to provide improved photo-resist composition having high light-sensitivity, high resolution, excellent developer resistance and excellent resistance to thermal flow.Type: GrantFiled: June 19, 1992Date of Patent: January 12, 1993Assignee: Shipley Company Inc.Inventors: Anthony Zampini, David C. Madoux, Peter Trefonas, III, Charles R. Szmanda
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Patent number: 5173389Abstract: A positive-working photoresist composition is disclosed, which comprises (1) a light-sensitive material obtained by reacting a polyhydroxy compound containing at least one group represented by the following general formula (I) per molecule with at least one of 1,2-naphthoquinonediazido-5-sulfonyl chloride and 1,2-naphthoquinonediazido-4-sulfonyl chloride, and (2) an alkali-soluble novolak resin: ##STR1## wherein R.sub.1 and R.sub.2 each represents a hydrogen atom or a C.sub.1 -C.sub.4 straight or branched alkyl or alkoxy group, provided that R.sub.1 and R.sub.2 do not represent hydrogen atoms at the same time; and X represents a divalent organic group.Type: GrantFiled: April 26, 1990Date of Patent: December 22, 1992Assignee: Fuji Photo Film Co., Ltd.Inventors: Kazuya Uenishi, Shinji Sakaguchi, Tadayoshi Kokubo
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Patent number: 5166036Abstract: The invention provides an aqueous electrodeposition coating composition for a positive working resist and an image-forming method using the same. The coating composition is very stable under storage conditions and is capable of resulting in a positive working resist which is specifically useful in the preparation of a printed circuit board with mini-via-holes.Type: GrantFiled: July 9, 1991Date of Patent: November 24, 1992Assignee: Nippon Paint Co., Ltd.Inventors: Mamoru Seio, Takeshi Ikeda, Kanji Nishijima, Katsukiyo Ishikawa
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Patent number: 5166033Abstract: Disclosed herein is a positive resist composition comprising an alkali-soluble phenolic resin and the quinonediazide sulfonate of at least one phenolic compound selected from vinylphenol compounds and isopropenylphenol compounds as a photosensitive agent. It is suitable for use in minute processing.Type: GrantFiled: September 25, 1990Date of Patent: November 24, 1992Assignee: Nippon Zeon Co., Ltd.Inventors: Masayuki Oie, Shoji Kawata, Takamasa Yamada
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Patent number: 5162190Abstract: A compound of the general formula I ##STR1## in which D denotes a 1,2-naphthoquinone-2-diazide-4-sulfonyl or - 5-sulfonyl radical,R.sup.1 denotes an alkylene group andR.sup.2 denotes a hydrogen atom, an alkyl group or a group R.sup.1 --OH,or of the general formula II ##STR2## in which X denotes an alkylene group, an arylene group or a group of the formulaNH--Y--NH,wherein Y is an alkylene group or an arylene group,R.sup.3 denotes an alkylene group, which may be interrupted by ether oxygen atoms,n is a number from 1 to 40 andm is a number from 0 to 50,the ratio m:(m+n) being from 0:100 to 95:100 and R.sup.1 and D having the above-indicated meaning, are disclosed. The compounds may be used in positive-working photosenitive materials for the production of printing plates and photoresists. Compounds according to formula II do not require an addition of polymeric binders.Type: GrantFiled: June 29, 1989Date of Patent: November 10, 1992Assignee: Hoechst AktiengesellschaftInventors: Wolfgang Zahn, Gerhard Buhr, Hartmut Steppan
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Patent number: 5145763Abstract: A positive photoresist composition containing (i) a quinone diazide polymer formed by reacting a cresol-formaldehyde novolac resin and an o-quinonediazide compound, and (ii) a sulfonamide development enhancement agent.Type: GrantFiled: June 29, 1990Date of Patent: September 8, 1992Assignee: OCG Microelectronic Materials, Inc.Inventors: David R. Bassett, Gary A. Amstutz
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Patent number: 5132376Abstract: Process for producing dimer-free phenolic polymers, particularly novolak polymers produced from cresol mixtures, and photoresist compositions containing such dimer-free novolak polymers. The process comprises reacting phenolic polymers containing phenolic dimers with a capping agent, such as a silylating agent, to cap all of the phenolic hydroxy groups. This reduces the distillation temperature of the capped dimers and renders the capped polymer stable at such distillation temperature. The capped dimers are distilled off, and finally the phenolic polymer is uncapped. Dimer-free novolaks produce scum-free developed photoresist images.Type: GrantFiled: December 20, 1990Date of Patent: July 21, 1992Assignee: OCG Microelectronic Materials, Inc.Inventor: Thomas R. Sarubbi
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Patent number: 5128230Abstract: This invention is directed to novel photoresist processes and compositions having high resolution novalac resins, high resolution photoactive components with several diazoquinone groups per molecule, and solvents having a high solvency power, better safety, improved photospeed, higher contrast and equivalent cast film thickness from lower percent solids formulations.Type: GrantFiled: January 23, 1991Date of Patent: July 7, 1992Assignee: Shipley Company Inc.Inventors: Michael K. Templeton, Anthony Zampini, Peter Trefonas, III, James C. Woodbrey, David C. Madoux, Brian K. Daniels
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Patent number: 5116715Abstract: A photosensitive composition having increased contrast and selectivity, useful in forming high resolution patterns. The composition comprises a phenolic resin, a diazoquinone compound and an aromatic fused polycyclic sulfonic or carboxylic acid, in the form of the free acid and/or an ammonium salt and/or an acid halide, the cation component of the ammonium salt having the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4, each represent hydrogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -hydroxyalkyl.In forming a negative pattern, the composition is coated on a substrate and exposed imagewise to ultraviolet radiation, thereafter treated with a silicon compound, whereby the silicon compound is selectively absorbed into the irradiated portions and the nonirradiated portions are then removed by dry etching.Type: GrantFiled: March 8, 1991Date of Patent: May 26, 1992Assignee: U C B S.A.Inventors: Bruno Roland, Jan Vandendriessche, Catherine Jakus
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Patent number: 5112719Abstract: Disclosed herein is a positive resist composition comprising an alkali-soluble phenolic resin, a photosensitive agent formed of a quinonediazide sulfonic acid ester and at least one compound represented by the following general formula (I): ##STR1## wherein R.sup.1 through R.sup.6 mean individually a hydrogen or halogen atom, a hydroxyl group or an alkyl or alkenyl group having 1-4 carbon atoms and may be equal to or different from one another,R.sup.7 and R.sup.8 denote individually a hydrogen or halogen atom, or an alkyl group having 1-4 carbon atoms and may be equal to or different from each other, andR.sup.9 through R.sup.11 stand individually for a hydrogen atom or an alkyl group having 1-4 carbon atoms and may be equal to or different from one another. It is suitable for use in minute processing.Type: GrantFiled: October 26, 1990Date of Patent: May 12, 1992Assignee: Nippon Zeon Co., Ltd.Inventors: Takamasa Yamada, Shoji Kawata, Masayuki Oie
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Patent number: 5110706Abstract: A radiation-sensitive resin composition comprises (a) an alkali-soluble resin, (b) a 1,2-quinone diazide compound, and (c) an aromatic compound having a specified molecular structure, as essential constituents. The composition is extremely useful for forming a positive type photoresist on a substrate having a high reflectance.Type: GrantFiled: November 13, 1990Date of Patent: May 5, 1992Assignee: Japan Synthetic Rubber Co., Ltd.Inventors: Yoshiji Yumoto, Tsutomu Shimokawa, Takao Miura
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Patent number: 5106718Abstract: The invention relates to positive photoresists based on alkali-soluble phenolic resin and photosensitive quinonediazide compounds which, by means of particular additives, give relief structures produced therewith an increased stability towards changes due to thermal effects.Type: GrantFiled: February 1, 1991Date of Patent: April 21, 1992Assignee: Ciba-Geigy CorporationInventors: Ekkehard Bartmann, Reinhard Schulz, Horst Munzel
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Patent number: 5094936Abstract: A process for silylation of positive or negative photosensitive resist layer on a semiconductor wafer after the resist layer has been exposed to radiant energy through a mask which includes introducing a silylating agent to the wafer at high pressure over 760 torr and, usually, at temperatures less than 180.degree. C. Increased pressure increases the rate of silylation, allows practical use of lower process temperatures, and, therefore, allows better process control. Also an apparatus is disclosed for applying the high pressure silylation process to a wafer.Type: GrantFiled: June 26, 1990Date of Patent: March 10, 1992Assignee: Texas Instruments IncorporatedInventors: George R. Misium, Cesar M. Garza, Cecil J. Davis
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Patent number: 5087547Abstract: The resolution and stability of liquid, dual-tone photoresist formulations containing novolac resins and photoactive compounds are enhanced by the incorporation therein of certain carbodiimide resolution enhancers.Type: GrantFiled: March 2, 1990Date of Patent: February 11, 1992Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: James W. Taylor, David R. Bassett
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Patent number: 5080998Abstract: A process for the formation of an image comprises(i) electrodepositing on a conductive surface a photosensitive film from an aqueous composition which is a solution or dispersion comprising a mixture of (A) a photosensitive o-quinone diazide such as an o-naphthoquinone diazide sulfonyl ester of a phenol, and (B) an electrodepositable film-forming resin such as a reaction product of a novolak resin, formaldehyde and diethanolamine in (C) an aqueous medium, the composition being substantially free from a resin having both a quinone diazide residue and a carboxyl, phosphonic or sulfonic acid group or amino group in the same molecule,(ii) subjecting the electrodeposited film to radiation in a predetermined pattern, such that exposed areas of the film become more soluble in aqueous base than unexposed areas, and(iii) removing the exposed areas by treatment with an aqueous base.The process is useful in the production of printing plates and printed circuits.Type: GrantFiled: December 17, 1990Date of Patent: January 14, 1992Assignee: Ciba-Geigy CorporationInventors: Edward Irving, Christopher G. Demmer, Jane Wilkerson
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Patent number: 5063134Abstract: A photosensitive composition contains a polymer having a unit represented by formula I, and a photosensitive agent: ##STR1## wherein each of R.sub.1 to R.sub.4 represents a hydrogen atom, an alkyl group, an alkoxyl group, or a substituted or non-substituted allyl group, at least one of R.sub.1 to R.sub.4 being an alkyl groups having 1 to 10 carbon atoms and containing silicon, l represents a positive integer, and each of a and b represents an integer from 1 to 3, and c represents an integer from 0 to 2, a+b+c not exceeding 4.Type: GrantFiled: January 2, 1990Date of Patent: November 5, 1991Assignee: Kabushiki Kaisha ToshibaInventors: Rumiko Horiguchi, Shuzi Hayase, Yasunobu Onishi
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Patent number: 5055374Abstract: The invention provides an aqueous electrodeposition coating composition for a positive working resist and an image-forming method using the same. The coating composition is very stable under storage conditions and is capable of resulting in a positive working resist which is specifically useful in the preparation of a printed circuit board with mini-via-holes.Type: GrantFiled: August 2, 1989Date of Patent: October 8, 1991Assignee: Nippon Paint Co., Ltd.Inventors: Mamoru Seio, Takeshi Ikeda, Kanji Nishijima, Katsukiyo Ishikawa
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Patent number: 5037720Abstract: A photosensitive alkali-soluble, thermally-stable fluorinated hydroxy-resinous polyamide or polyimide composition comprising a resin-bound diazo sensitizer incorporated by the reaction of an o-quinone diazide sulfonyl chloride sensitizer compound with a predetermined percentage of the hydroxy groups of the hydroxy-resin binder material. The present compositions are self-sensitized, have adjustable alkali-solubility and provide high speed photoresist compositions for producing relief patterns having good edge definition and high thermal stability.Type: GrantFiled: June 8, 1989Date of Patent: August 6, 1991Assignee: Hoechst Celanese CorporationInventor: Dinesh N. Khanna
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Patent number: 5011753Abstract: Heat resistant, shapable, hydroxy and/or alkoxy-substituted polyamides derived from at least one diamine selected from unsubstituted and substituted 4,4'-bis[2-(4-amino-3-hydroxyphenyl)hexafluoroisopropyl)]diphenyl ether 4,4'-bis-[2-(3-amino-4-hydroxyphenyl)hexafluoroisopropyl]diphenyl ether and a dicarboxylic acid or a derivative thereof e.g. its acid halo or ester. The polyamides of the invention may be thermally cured to form polybenzoxazoles of higher heat resistance which are stable to hydrolytic, chemical and radiation attack.The polyamides of the invention may be formed into shaped articles by molding, extrusion and solvent casting processes preferably in the presence of a solvent or diluent and then optionally converted into heat resistant, insoluble polybenzoxazoles. These shaped articles are useful in aircraft, electronic and other commercial applications where heat, chemical and radiation resistance are desired in conjunction with good mechanical and electrical properties.Type: GrantFiled: February 7, 1990Date of Patent: April 30, 1991Assignee: Hoechst Celanese CorporationInventors: Werner H. Mueller, Dinesh N. Khanna
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Patent number: 5002858Abstract: A process for the formation of an image comprises(i) electrodepositing on a conductive surface a layer of a quinone diazide positive photoresist,(ii) subjecting the layer to radiation in a predetermined pattern,(iii) heating the layer such that areas thereof exposed in stage (ii) are rendered insoluble in an aqueous base developer,(iv) subjecting the layer to radiation such that the areas not exposed in stage (ii) are rendered more soluble in an aqueous base developer than the areas rendered insoluble in stage (iii) and(v) removing the areas not exposed in stage (ii) by treatment with an aqueous base developer.The process is useful in the production of printing plates and printed circuits.Type: GrantFiled: November 7, 1989Date of Patent: March 26, 1991Assignee: Ciba-Geigy CorporationInventors: Christopher G. Demmer, Edward Irving
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Patent number: 4999274Abstract: The invention provides a positive type photosensitive resinous composition comprising a resin obtained by the reaction of a polyepoxide compound, an aromatic or heterocyclic carboxylic acid bearing a phenolic hydroxyl group(s) and 1,2-quinondiazido sulfonic acid halide with the use of those three components in a defined proportion, which is useful for microfabrication photo-resist and photosensitive materials for use in lithographic plates because of excellent flexibility and adhesion to supporting substrates, when developed, non-exposed area are extremely resistive toward swelling.Type: GrantFiled: October 27, 1988Date of Patent: March 12, 1991Assignee: Nippon Paint Co., Ltd.Inventors: Mamoru Seio, Kanji Nishijima, Katsukiyo Ishikawa
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Patent number: 4992596Abstract: A trinuclear novolak oligomer of the formula (I): ##STR1## wherein each X is selected from the group consisting of hydroxyl group and halide group and Y is selected from the group consisting of a lower alkyl group having 1-4 carbon atoms and halogen atom.Type: GrantFiled: June 8, 1990Date of Patent: February 12, 1991Assignee: Olin Hunt Specialty Products Inc.Inventors: Alfred T. Jeffries, III, Andrew J. Blakeney, Medhat A. Toukhy
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Patent number: 4975351Abstract: A positive-type photosensitive electrodeposition coating composition comprising as a main component a water-soluble or water-dispersible resin containing modified quinonediazidesulfone units represented by the following formula (I) ##STR1## wherein R.sub.1 represents ##STR2## or ##STR3## 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 or an alkylene ether group, in the molecule.Type: GrantFiled: November 7, 1988Date of Patent: December 4, 1990Assignee: Kansai Paint Co., Ltd.Inventors: Yuu Akaki, Kenji Seko, Toshio Kondo, Naozumi Iwasawa
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Patent number: 4963463Abstract: A radiation-sensitive resin composition comprising a quinonediazide-type radiation-sensitive resin and a compound generating an acid upon irradiation. Said radiation-sensitive resin composition can be used as a resist suitable for dry development by plasma etching and enables one to obtain an etching image having high precision with high reproducibility at a high degree of resolution and selectivity.Type: GrantFiled: February 15, 1989Date of Patent: October 16, 1990Assignees: Japan Synthetic Rubber Co., Ltd., UCB Societe AnonymeInventors: Mitsunobu Koshiba, Keiichi Yamada, Yoshiyuki Harita, Bruno Roland, Jan Vandendriesshe
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Patent number: 4959292Abstract: A phenolic novolak resin comprising the product of a condensation reaction of an aldehyde comprising a haloacetaldehyde source or a mixture of a haloacetaldehyde source and a formaldehyde source with a phenolic monomer comprising at least one compound of the formula: ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are individually selected from hydrogen or a one to four carbon alkyl group and wherein the ratio of total carbon atoms in the sum of R.sub.1, R.sub.2 and R.sub.3 to the total number of phenolic nuclei in said resin is from about 0.5:1 to about 1.5:1 in the presence of a solvent; said resin made by employing a molar ratio of total aldehyde to total phenolic monomers from about 0.33:1 to about 0.70:1. These phenolic resins are suitable for use in light-sensitive compositions (e.g. positive-working photoresists).Type: GrantFiled: July 11, 1988Date of Patent: September 25, 1990Assignee: Olin Hunt Specialty Products Inc.Inventors: Andrew J. Blakeney, Thomas Sarubbi, Joseph J. Sizensky