Patents Assigned to OCG Microelectronic Materials, Inc.
-
Patent number: 5776657Abstract: Photoresist compositions are described, which are sufficiently transparent in the solvent-free state for radiation of a wavelength of approximately 193 nm, and which contain nonaromatic chemical groups, which can be converted into groups with aromatic structural elements (latent aromatic groups) under process conditions, for which an image structure comprised of the resist material is not disrupted. A preferred component with latent aromatic groups is bicyclo?3.2.2!nona-6,8-dien-3-one Resist coatings, which are produced with these compositions, show a stability in plasma etching, which is comparable with the stability of conventional resists based on phenolic resins.Type: GrantFiled: March 14, 1996Date of Patent: July 7, 1998Assignee: OCG Microelectronic Materials, Inc.Inventors: Ulrich Schaedeli, Manfred Hofmann, Norbert Muenzel, Arnold Grubenmann
-
Patent number: 5663038Abstract: A process for the preparation of phenolic resins having acid-labile acetal or ketal protecting groups by reacting a phenolic resin with an enol ether in the presence of an acidic catalyst and subsequently treating the reaction mixture with a basic anion exchanger gives heat-resistant polymers which, in combination with acid photogenerators, produce radiation-sensitive compositions of high processing stability with a greatly improved shelf life.Type: GrantFiled: December 14, 1995Date of Patent: September 2, 1997Assignee: OCG Microelectronic Materials, Inc.Inventors: Carl-Lorenz Mertesdorf, Bertold Nathal, Hans-Jorg Kirner
-
Patent number: 5648324Abstract: A photoresist stripping composition containing:(a) 20-70% by weight of an organic polar solvent having a dipole moment of more than 3.5;(b) 70-20% by weight of alkanolamine compounds; and(c) 0.1-10% by weight of 2,2'[[methyl-1H-benzothiazol-1-yl)methyl]imino]bis-ethanol.Type: GrantFiled: January 23, 1996Date of Patent: July 15, 1997Assignee: OCG Microelectronic Materials, Inc.Inventors: Kenji Honda, Donald F. Perry, Taishih Maw
-
Patent number: 5602260Abstract: A photosensitive compound comprising at least one o-quinonediazide sulfonic acid ester of a phenolic compound, said esters selected from the group consisting of formulae (IB) and (IIB): ##STR1## wherein the variables are as defined in the description.Type: GrantFiled: May 26, 1995Date of Patent: February 11, 1997Assignee: OCG Microelectronic Materials, Inc.Inventors: Andrew J. Blakeney, Arturo N. Medina, Medhat A. Toukhy, Lawrence Ferreira, Sobhy Tadros
-
Patent number: 5597678Abstract: A non-corrosive positive photoresist stripper composition comprising:(a) a solvent selected from N-methyl-2-pyrrolidone, N-hydroxyethyl-2-pyrrolidone, 1,3-dimethyl-2-imidazolidinone dimethylsulfoxide, and admixtures thereof;(b) a corrosion inhibitor selected form tricine, bicine, (2-benzothiozolythio)succinic acid, and admixtures thereof;(c) optionally, an alkanolamine selected from diethyleneglycolamine, monoethanolamine, diethanolamine, triethanolamine, and admixtures thereof;(d) optionally, water; and(e) optionally, a water-soluble surface active compound.Type: GrantFiled: July 7, 1995Date of Patent: January 28, 1997Assignee: OCG Microelectronic Materials, Inc.Inventors: Kenji Honda, Donald F. Perry, Taishih Maw
-
Patent number: 5565304Abstract: A chemically amplified-type radiation-sensitive composition comprising:(a) an alkali-soluble binder resin made by a condensation reaction of:(i) hydroxystyrene moiety having formula [1] or [2]: ##STR1## wherein x is an integer from 2 to 300; with (ii) a monomethylolated phenolic compound having a formula [8]: ##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.Type: GrantFiled: June 5, 1995Date of Patent: October 15, 1996Assignee: OCG Microelectronic Materials, Inc.Inventor: Kenji Honda
-
Patent number: 5561105Abstract: A non-corrosive photoresist composition containing:(a) 20-70% by weight of an organic polar solvent having a dipole moment of more than 3.5;(b) 70-20% by weight of selected amine compounds;(c) an effective amount of a chelating reagent comprising a mono- or poly-valent acid type of ligand covalently attached to a polymeric or oligomeric backbone; and(d) optionally 0-10% by weight of selected amino acid having a hydroxyl group.Type: GrantFiled: May 8, 1995Date of Patent: October 1, 1996Assignee: OCG Microelectronic Materials, Inc.Inventor: Kenji Honda
-
Patent number: 5558978Abstract: The invention relates to novel maleimide copolymers which, in addition to structural units derived from certain maleimide derivatives defined more precisely in the present patent application, comprises recurring structural units selected from the structural units of the formulae (Ia) and (Ib) ##STR1## where A is a direct single bond or a divalent group of the formula --O--;R.sub.0 and R.sub.1, independently of one another, are each a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group or an aryl group having 6 to 14 ring carbon atoms;R.sub.2 is a radical of the formula ##STR2## in which R is a tert-alkyl radical having 4 to 19 carbon atoms,[T] is a C.sub.1 -C.sub.6 alkylene group or an arylene group having 6 to 14 ring carbon atoms, and p is the number 2, 3 or 4; orA together with R.sub.2 is a group of the formula ##STR3## and where, furthermore, R.sub.3 and R.sub.4, independently of one another, are each a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.6 alkyl group or a C.sub.1 -C.sub.Type: GrantFiled: December 16, 1994Date of Patent: September 24, 1996Assignee: OCG Microelectronic Materials, Inc.Inventors: Ulrich Sch adeli, Norbert M unzel, Christoph De Leo, Heinz Holzwarth, Eric Tinguely
-
Patent number: 5554797Abstract: 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: GrantFiled: March 7, 1995Date of Patent: September 10, 1996Assignee: OCG Microelectronic Materials, Inc.Inventors: Reinhard Schulz, Norbert M unzel, Martin Roth, Wilhelm Knobloch
-
Patent number: 5550004Abstract: A chemically amplified-type radiation-sensitive composition comprising:(a) an alkali-soluble binder resin made by a condensation reaction of:(i) hydroxystyrene moiety having formula [1] or [2]: ##STR1## wherein x is an integer from 2 to 300; with (ii) a monomethylolated phenolic compound having a formula [8]: ##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.Type: GrantFiled: August 19, 1994Date of Patent: August 27, 1996Assignee: OCG Microelectronic Materials, Inc.Inventor: Kenji Honda
-
O-quinonediazide sulfonic acid esters of phenolic compounds and their use in forming positive images
Patent number: 5547814Abstract: A photosensitive compound comprising at least one o-quinonediazide sulfonic acid ester of a phenolic compound, said esters selected from the group consisting of formulae (IB) and (IIB): ##STR1## wherein the photosensitive compound is used in a radiation sensitive composition and a process for forming a positive patterned image.Type: GrantFiled: May 26, 1995Date of Patent: August 20, 1996Assignee: OCG Microelectronic Materials, Inc.Inventors: Andrew J. Blakeney, Arturo N. Medina, Medhat A. Toukhy, Lawrence Ferreira, Sobhy Tadros -
Patent number: 5545353Abstract: A non-corrosive photoresist composition containing:(a) 20-70% by weight of an organic polar solvent having a dipole moment of more than 3.5;(b) 70-20% by weight of selected amine compounds;(c) 0.1-10% by weight of (2-benzothiozolylthio)succinic acid.Type: GrantFiled: May 8, 1995Date of Patent: August 13, 1996Assignee: OCG Microelectronic Materials, Inc.Inventors: Kenji Honda, Taishih Maw
-
Patent number: 5541033Abstract: A photosensitive compound comprising at least one o-quinonediazide sulfonic acid ester of a phenolic compound, said esters selected from the group consisting of formulae (IB) and (IIB): ##STR1## wherein the photosensitive compound is used in a positive photoresist composition and process for forming patterned image. Further the invention is drawn to a positive photoresist composition comprising an alkali-soluble resin and quinone diazide sulfonic acid triesters and diesters characterized by their HPLC peak areas.Type: GrantFiled: February 1, 1995Date of Patent: July 30, 1996Assignee: OCG Microelectronic Materials, Inc.Inventors: Andrew J. Blakeney, Arturo N. Medina, Medhat A. Toukhy, Lawrence Ferreira, Sobhy Tadros
-
Patent number: 5507978Abstract: A noncorrosive photoresist composition containing:(a) 20-70% by weight of an organic polar solvent having a dipole moment of more than 3.5;(b) 70-20% by weight of selected amine compounds;(c) about 0.01% to about 1% by weight of novolak resin having a weight-average molecular weight (M.sub.w) from about 200 to about 5,000;(d) optionally 0-10% by weight of selected amino acid having a hydroxyl group; and(e) optionally 0-10% by weight of water.Type: GrantFiled: May 8, 1995Date of Patent: April 16, 1996Assignee: OCG Microelectronic Materials, Inc.Inventor: Kenji Honda
-
Patent number: 5494785Abstract: A phenolic novolak composition prepared by a process comprising the steps of:(1) reacting a first phenolic monomer comprising a major portion of at least one trifunctional phenolic monomer with a first aldehyde source in the absence of a catalyst at a reaction temperature from about 100.degree. C. to about 200.degree. C. and at a reaction pressure of about 2 to about 15 atmospheres to form a phenolic oligomer having a weight average molecular weight from about 500 to about 2,000, having ortho-ortho bonding of about 55% to about 75% of the methylene bonds between the phenolic moieties; and having a time to clear of less than 125 seconds per micron; wherein the mole ratio of said first aldehyde source to said first phenolic monomer is from about 0.3:1.0 to about 0.55:1.0; and(2) then reacting said oligomer with an optional second phenolic source and a second aldehyde source at a temperature from about 80.degree. C. to about 150.degree. C.Type: GrantFiled: January 17, 1995Date of Patent: February 27, 1996Assignee: OCG Microelectronic Materials, Inc.Inventors: Joseph J. Sizensky, Thomas R. Sarubbi, Medhat A. Toukhy
-
Patent number: 5473045Abstract: A phenolic novolak composition prepared by a process comprising the steps of:(1) reacting a first phenolic monomer comprising a major portion of at least one trifunctional phenolic monomer with a first aldehyde source in the absence of a catalyst at a reaction temperature from about 100.degree. C. to about 200.degree. C. and at a reaction pressure of about 2 to about 15 atmospheres to form a phenolic oligomer having a weight average molecular weight from about 500 to about 2,000, having ortho--ortho bonding of about 55% to about 75% of the methylene bonds between the phenolic moieties; and having a time to clear of less than 125 seconds per micron; wherein the mole ratio of said first aldehyde source to said first phenolic monomer is from about 0.3:1.0 to about 0.55:1.0; and(2) then reacting said oligomer with an optional second phenolic source and a second aldehyde source at a temperature from about 80.degree. C. to about 150.degree. C.Type: GrantFiled: January 17, 1995Date of Patent: December 5, 1995Assignee: OCG Microelectronic Materials, Inc.Inventors: Joseph J. Sizensky, Thomas R. Sarubbi, Medhat A. Toukhy
-
Patent number: 5472830Abstract: A non-corrosive photoresist stripping composition containing:(a) 85-10% by weight of an organic polar solvent having a dipole moment of more than 3.5;(b) 10-40% by weight of selected amine compounds;(c) 5-30% by weight of selected amino acid having a hydroxyl group; and, optionally,(d) 0-20% by weight water.Type: GrantFiled: April 18, 1994Date of Patent: December 5, 1995Assignee: OCG Microelectronic Materials, Inc.Inventor: Kenji Honda
-
Patent number: 5462207Abstract: A reusable, high purity liquid chemical dispensing assembly is provided for use in a production line that processes chemically treated articles such as semiconductors. This dispensing assembly contains a high purity liquid chemical, such as photoresist, which it dispenses into a production line application station. The dispensing assembly can be disconnected from the production line when it is essentially emptied of the liquid chemical, and can be then rinsed and purged of chemical residue, and refilled with fresh chemical. The rinsing, purging, and refilling operations are performed in an environmentally safe manner. By providing a reusable dispensing assembly the problem of disposing of chemically polluted containers is eliminated.Type: GrantFiled: October 19, 1994Date of Patent: October 31, 1995Assignee: OCG Microelectronic Materials, Inc.Inventor: Ivan S. Daraktchiev
-
Patent number: 5446125Abstract: A method of removing metal impurities from a resist component, comprising the steps of:(a) dissolving said resist component in a solvent;(b) contacting said resist component solution with a cation exchange resin and a chelate resin for a sufficient amount of time to absorb at least a portion of said metal impurities onto said cation exchange and chelate resins; and(c) separating said cation exchange and chelate resins bearing said metal impurities from said resist component solution.Type: GrantFiled: September 3, 1991Date of Patent: August 29, 1995Assignee: OCG Microelectronic Materials, Inc.Inventors: Kenji Honda, Edward A. Fitzgerald, Lawrence Ferreira
-
Patent number: 5446126Abstract: A method of removing metal impurities from a resist component, comprising the steps of:(a) dissolving said resist component in a solvent;(b) washing a cation exchange resin with a solution of a quaternary ammonium compound;(c) contacting the prewashed cation exchange resin with the solution of resist component to remove metal impurities from said solution of resist component; and(d) separating said cation exchange resin bearing said metal impurities from said resist component solution.Type: GrantFiled: September 3, 1991Date of Patent: August 29, 1995Assignee: OCG Microelectronic Materials, Inc.Inventor: Kenji Honda