Patents Assigned to Olin Microelectronic Chemicals, Inc.
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Patent number: 6042989Abstract: A radiation sensitive composition comprising (a) a terpolymer containing 20 to 70 mole percent of an acid-labile repeating unit, 3 to 40 mole percent of an acrylic or acrylonitrile based repeating unit and a repeating unit containing silicon side-chains and (b) a photo-acid generator. The silicon content of terpolymer is 7 to 20 weight percent. The composition is used primarily in the formulation of multilayer positive operating photoresists.Type: GrantFiled: October 26, 1998Date of Patent: March 28, 2000Assignee: Olin Microelectronic Chemicals, Inc.Inventors: Ulrich Schaedeli, Eric Tinguely, Manfred Hofmann, Pasquale Alfred Falcigno, Carl-Lorenz Mertesdorf
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Patent number: 6040107Abstract: A photosensitive compound comprising at least one o-quinonediazide sulfonic acid ester of a phenolic compound, said esters selected from the group consisting of formula (II): ##STR1## wherein the photosensitive compound is used in a radiation sensitive composition and a process for forming a positive patterned image.Type: GrantFiled: February 6, 1998Date of Patent: March 21, 2000Assignee: Olin Microelectronic Chemicals, Inc.Inventors: Andrew J. Blakeney, Arturo N. Medina, Medhat A. Toukhy, Lawrence Ferreira, Alfred T. Jeffries, III, Ahmad A. Naiini
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Patent number: 6033993Abstract: A process of treating a substrate having photoresist applied thereto, comprising the steps of:(a) removing said photoresist from said substrate by a method selected from the group consisting of photoresist stripping, plasma etch residue cleaning, or a combination thereof; and(b) rinsing said substrate with a non-corrosive rinsing composition comprising(1) water; and(2) one or more water-soluble corrosion inhibitors selected from the group consisting essentially of hydroxylamine, at least one hydroxylammonium salt, at least one water-soluble organic acid, at least one amino acid, and combinations thereof.Type: GrantFiled: September 23, 1997Date of Patent: March 7, 2000Assignee: Olin Microelectronic Chemicals, Inc.Inventors: M. Lee Love, Jr., Kenji Honda
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Patent number: 6028154Abstract: A terpolymer containing 20 to 70 mole percent of an acid labile repeating unit, 3 to 40 mole percent of an acrylonitrile based repeating unit and a repeating unit containing silicon side chains. The silicon side chain repeating unit is provided in sufficient amounts so that the terpolymer silicon content is 7 to 20 weight percent. The terpolymer is used primarily in the formulation of multilayer positive operating photoresists.Type: GrantFiled: October 26, 1998Date of Patent: February 22, 2000Assignee: Olin Microelectronic Chemicals, Inc.Inventors: Ulrich Schaedeli, Eric Tinguely, Manfred Hofmann, Pasquale Alfred Falcigno, Carl-Lorenz Mertesdorf
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Patent number: 6027853Abstract: The present invention relates to a process for preparing a radiation-sensitive composition, comprising the steps of (1) passing a solution of a crude polymer comprising a mixture of polymer chains having different molecular weights through a porous polymeric media having a predetermined molecular weight cut-off (MWCO) value, thereby separating the crude polymeric mixture into a first fraction comprising polymer chains having molecular weights above the MWCO value and a second fraction comprising polymer chains having molecular weights below the MWCO value; and (2) adding at least one fraction produced in the first step to at least one radiation-sensitive compound and at least one solvent to produce a radiation-sensitive composition.Type: GrantFiled: January 16, 1998Date of Patent: February 22, 2000Assignee: Olin Microelectronic Chemicals, Inc.Inventors: Sanjay Malik, Andrew J. Blakeney, Joseph J. Sizensky
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Patent number: 6020292Abstract: A non-corrosive cleaning composition for removing plasma etching residues comprising water, at least one quaternary ammonium hydroxide, and at least one corrosion inhibitor selected from (i) quaternary ammonium silicates and (ii) catechol nucleus-containing oligomers having a molecular weight in the range of about 220 to about 5,000.Type: GrantFiled: May 21, 1998Date of Patent: February 1, 2000Assignee: Olin Microelectronic Chemicals, Inc.Inventors: Kenji Honda, Taishih Maw
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Patent number: 6010825Abstract: A negatively operating photoresist composition comprising: (a) a polyimide precursor containing repeating structural units of formula (1) ##STR1## the composition comprises in all as many structural units of formula (I), which have residues R.sub.2, that the composition can be developed by means of aqueous-alkaline developers for photoresists, which are free of organic solvents.Type: GrantFiled: September 10, 1998Date of Patent: January 4, 2000Assignee: Olin Microelectronics Chemicals, Inc.Inventors: Sigurd Hagen, Nadia Reichlin
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Patent number: 5985507Abstract: A high thermal alkali-soluble novolak binder resin, comprising the addition-condensation reaction product of a phenolic mixture with at least one aldehyde source, the feedstock of the phenolic mixture for the reaction comprising:(1) about 25 to about 40 weight percent of the phenolic mixture being a monomer selected from meta-cresol 2,5-xylenol or the combination thereof;(2) about 50 to about 70 weight percent of the phenolic mixture being para-cresol; and(3) about 3 to about 20 weight percent of the phenolic mixture being acetamidophenol; all percentages based on the weight of total phenol monomer feedstock.The invention is also directed to a positive working photoresist made from the composition.Type: GrantFiled: February 18, 1998Date of Patent: November 16, 1999Assignee: Olin Microelectronic Chemicals, Inc.Inventors: Andrew J. Blakeney, Sanjay Malik, Medhat A. Toukhy, Joseph Sizensky
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Patent number: 5928818Abstract: Polymers having an average molecular weight M.sub.w (weight average) of 5,000 to 1,000,000 (measured by gel permeation chromatography), comprising structural repeating units of the formulae I-IV: ##STR1## in which R.sub.1, R.sub.2, R.sub.3 and R.sub.4 independently of one another are hydrogen, methyl or halogen, R.sub.5 and R.sub.6 independently of one another are C.sub.1 -C.sub.6 alkyl, R.sub.7, R.sub.8, R.sub.9 and R.sub.10 independently of one another are hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen, and w, x, y and z are numbers equal to or greater than 1, with the provision that the quotient ##EQU1## which is obtainable from the sum of the structural units having protecting groups divided by the sum of all of the structural units present, obeys the condition 0.10.ltoreq.Q.ltoreq.0.50, are suitable as binders for DUV photoresists of high processing stability and flow resistance.Type: GrantFiled: February 26, 1997Date of Patent: July 27, 1999Assignee: Olin Microelectronic Chemicals, Inc.Inventors: Carl-Lorenz Mertesdorf, Hans-Thomas Schacht, Norbert Muenzel, Pasquale Alfred Falcigno
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Patent number: 5886119Abstract: A terpolymer containing 20 to 70 mole percent of an acid labile repeating unit, 3 to 40 mole percent of an acrylic acid or acrylonitrile based repeating unit and a repeating unit containing silicon side chains. The silicon side chain repeating unit is provided in sufficient amounts so that the terpolymer silicon content is 7 to 20 weight percent. The terpolymer is used primarily in the formulation of multilayer positive operating photoresists.Type: GrantFiled: July 16, 1996Date of Patent: March 23, 1999Assignee: Olin Microelectronic Chemicals, Inc.Inventors: Ulrich Schaedeli, Eric Tinguely, Manfred Hofmann, Pasquale Alfred Falcigno, Carl-Lorenz Mertesdorf
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Patent number: 5863701Abstract: Novel polymers may be used in resist formulations for the fabrication of printing plates and circuit boards and, in particular, for the fabrication of integrated circuits. No autocatalytic decomposition of the compounds occurs and the resist film obtained therewith has good adhesive properties.Type: GrantFiled: May 5, 1998Date of Patent: January 26, 1999Assignee: Olin Microelectronic Chemicals, Inc.Inventor: Carl-Lorenz Mertesdorf
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Patent number: 5856065Abstract: Negative working photoresist compositions containing:a) a polyimide primer containing recurring structural units of formula (I) in the specification as well asb) a photoinitiator for polymerizing olefin double bonds, which are characterized by in that they containat least one other component c), which is selected from the group consisting ofc1) organosilicon compounds with one or more hydroxyl groups,c2) compounds of formula (IIa) in the specification,c3) compounds of formula (IIb) as in the specification,c4) mixtures comprised of two or more components selected from components of c1), c2) and c3),have the advantage that they can be developed with a developer, which comprises up to 50 to 100 wt. % of an aqueous-alkaline medium, whereby the balance to 100 wt. % is formed by one or more organic solvents.Type: GrantFiled: February 14, 1997Date of Patent: January 5, 1999Assignee: Olin Microelectronic Chemicals, Inc.Inventor: Sigurd Guenter Hagen
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Patent number: 5849808Abstract: A polymer which is insoluble in aqueous-alkaline developer solutions, and comprises structural units of the formula (I): ##STR1## in which R.sub.2 is hydrogen, C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.10 cycloalkyl, C.sub.5 -C.sub.14 aryl, C.sub.6 -C.sub.30 aralkyl, R.sub.3 is C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.10 cycloalkyl, C.sub.5 -C.sub.14 aryl, or C.sub.6 -C.sub.30 aralkyl, it being possible for the alkyl, cycloalkyl, aryl, or aralkyl groups to be substituted if desired by one or more hydroxyl groups or nitro groups or by one or more halogen atoms, and X is a k+1 valent organic radical, k being a number from 1 to 5, and 1 is a number from 0 to 4, in a quantity such that the cleavage products obtained by reaction with an acid are soluble in aqueous-alkaline developer solutions, is suitable as a binder for DUV photoresists of high processing stability, high contrast, and good resolution.Type: GrantFiled: April 19, 1996Date of Patent: December 15, 1998Assignee: Olin Microelectronic Chemicals, Inc.Inventors: Hans-Thomas Schacht, Norbert Muenzel
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Patent number: 5834581Abstract: A process for making polyimide-polyamic ester copolymer composition comprisingreacting at least one diamine, a pyromellitic diacid diester compound; at least one other tetracarboxylic diacid diester compound and a selected phosphoramide in the presence of a base catalyst to form a polyimide-polyamic acid ester copolymer.Type: GrantFiled: April 15, 1997Date of Patent: November 10, 1998Assignee: Olin Microelectronic Chemicals, Inc.Inventors: Ahmad Naiini, Steve L. C. Hsu, William D. Weber, Andrew J. Blakeney
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Patent number: 5834531Abstract: Radiation-sensitive compositions comprising a substance which forms acid under the action of actinic radiation and polymers based on combination of different repeating units derived from hydroxy styrene and hydroxy-vinylcyclohexane derivatives wherein a portion of the hydroxyl groups are replaced with either acid-labile acetal or ketal protecting groups and where a portion of the repeating groups comprise two crosslinked species connected via the protecting groups.Type: GrantFiled: October 29, 1997Date of Patent: November 10, 1998Assignee: Olin Microelectronic Chemicals, Inc.Inventors: Hans-Thomas Schacht, Norbert Muenzel, Carl-Lorenz Mertesdorf, Pasquale Alfred Falcigno, Heinz Holzwarth, Ottmar Rohde, deceased, Hans-Jorg Kirner
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Patent number: 5817610Abstract: A non-corrosive cleaning composition for removing plasma etching residues comprising water, at least one quaternary ammonium hydroxide, and at least one corrosion inhibitor selected from (i) quaternary ammonium silicates and (ii) catechol nucleus-containing oligomers having a molecular weight in the range of about 220 to about 5,000.Type: GrantFiled: September 6, 1996Date of Patent: October 6, 1998Assignee: Olin Microelectronic Chemicals, Inc.Inventors: Kenji Honda, Taishih Maw
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Patent number: 5798323Abstract: The present invention is directed to a non-corrosive photoresist stripping and cleaning composition, comprising:(a) about 5% to about 50% solvent selected from the group consisting of N-methyl-2-pyrrolidinone, N-hydroxyethyl-2-pyrrolidinone, 1,3-dimethyl-2-imidazolidinone, dimethylsulfoxide, N,N-dimethylacetamide, diacetone alcohol, ethylene glycol, propylene glycol and admixtures thereof;(b) about 10% to about 90% of an alkanolamine selected from the group consisting of diethyleneglycolamine, monoethanolamine, diethanolamine, triethanolamine, 2-(2-aminoethylamino)ethanol, and admixtures thereof;(c) about 0.1% to about 4% of Formula I: ##STR1## where R.sub.1 -R.sub.4 are individually selected from the group consisting of hydrogen, alkyl groups having 1-4 carbon atoms, alkoxy groups having 1-4 carbon atoms, halogen groups, amino groups, hydroxyl groups, carboxyl groups or combinations thereof; and(d) about 0.1% to about 40% of water, all percentages by weight of the total stripping and cleaning composition.Type: GrantFiled: May 5, 1997Date of Patent: August 25, 1998Assignee: Olin Microelectronic Chemicals, Inc.Inventors: Kenji Honda, Richard M. Molin, Gale L. Hansen
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Patent number: 5789525Abstract: A process for making polyimide composition comprising reacting at least one diamine, at least one tetracarboxylic diacid diester, selected phosphoramide and at least one base catalyst to form at least one polyimide compound, said reaction carried out at a temperature from about 20.degree. C. to about 60.degree. C. and wherein the molar ratio of diamine:tetracarboxylic diacid diester:phosphoramide:base catalyst is in the range of 0.8-1.2:1:2.5-4.0:2.5-4.0.Type: GrantFiled: April 15, 1997Date of Patent: August 4, 1998Assignee: Olin Microelectronic Chemicals, Inc.Inventors: Ahmad Naiini, Steve L. C. Hsu, William D. Weber, Andrew J. Blakeney
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Patent number: 5789524Abstract: A process for producing a polyimide composition by reacting at least one polyamic acid or at least one polyamic ester or a mixture of at least one polyamic acid and at least one polyamic ester with a selected phosphoramide in the presence of at least one base catalyst to from a polyimide composition.Type: GrantFiled: April 15, 1997Date of Patent: August 4, 1998Assignee: Olin Microelectronic Chemicals, Inc.Inventors: Steve L. C. Hsu, Ahmad Naiini, William D. Weber, Andrew J. Blakeney
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Patent number: 5780566Abstract: Novel polymers may be used in resist formulations for the fabrication of printing plates and circuit boards and, in particular, for the fabrication of integrated circuits. No autocatalytic decomposition of the compounds occurs and the resist film obtained therewith has good adhesive properties.Type: GrantFiled: October 26, 1995Date of Patent: July 14, 1998Assignee: Olin Microelectronic Chemicals, Inc.Inventor: Carl-Lorenz Mertesdorf