Patents by Inventor Richard A. DiPietro
Richard A. DiPietro has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 8633296Abstract: A composite hydrogel comprises an amphiphilic triblock copolymer (ABA) and a loaded micelle bound by noncovalent interactions. The loaded micelle comprises a biologically active substance and an amphiphilic diblock copolymer (CD). The A blocks comprise a steroidal repeat unit (repeat unit 1) having both a backbone carbonate and a side chain bearing a steroid functional group. Each of the A blocks has a degree of polymerization of about 0.5 to about 4.0. The B block comprises a first poly(alkylene oxide) backbone. The C block comprises a second poly(alkylene oxide) backbone. The D block comprises a steroidal repeat unit (repeat unit 2) having both a backbone carbonate group and a side chain comprising a steroid functional group. The composite hydrogel is capable of controlled release of the biologically active substance.Type: GrantFiled: September 12, 2012Date of Patent: January 21, 2014Assignees: International Business Machines Corporation, Agency for Science, Technology and ResearchInventors: Daniel J. Coady, Richard A. DiPietro, Amanda C. Engler, James L. Hedrick, Ashlynn L. Lee, Shrinivas Venkataraman, Yi Yan Yang
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Patent number: 7951525Abstract: Polymers for use in photoresist compositions include a repeat unit having a formula of: wherein Z represents a repeat unit of a polymer backbone; X is a linking group selected from the group consisting of alkylene, arylene, araalkylene, carbonyl, carboxyl, carboxyalkylene, oxy, oxyalkylene, and combinations thereof, and R is selected from the group consisting of hydrogen, alkyl, aryl, and cycloalkyl groups with the proviso that X and R are not part of the same ring system. Also disclosed are processes for patterning a relief image of the photoresist composition, wherein the photoresist composition has an outgassing rate of less than 6.5E+14 molecules/cm2/s.Type: GrantFiled: September 8, 2008Date of Patent: May 31, 2011Assignee: International Business Machines CorporationInventors: Richard A. DiPietro, Ratnam Sooriyakumaran, Sally A. Swanson, Hoa D. Truong
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Patent number: 7947425Abstract: Copolymers prepared by copolymerization of at least one fluorinated vinyl ether are provided. In one embodiment, the at least one fluorinated vinyl ether comprises ethylene directly substituted at an olefinic carbon atom with a moiety —OR* and optionally substituted with one, two, or three additional nonhydrogen substituents, wherein R* comprises a fluorinated alkyl moiety substituted with a protected or unprotected hydroxyl group, and further wherein an atom within R* may be (i) taken together with one of the additional nonhydrogen substituents, if present, or (ii) directly bound to an olefinic carbon atom, to form a ring. The polymers are useful, for example, in lithographic photoresist compositions, particularly chemical amplification resists. In a preferred embodiment, the polymers are substantially transparent to deep ultraviolet (DUV) radiation, and are thus useful in DUV lithographic photoresist compositions.Type: GrantFiled: August 7, 2006Date of Patent: May 24, 2011Assignee: International Business Machines CorporationInventors: Richard A. DiPietro, Hiroshi Ito
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Publication number: 20110053083Abstract: Photoresist compositions include a blend of a phenolic polymer with a (meth)acrylate-based copolymer free of ether-containing and/or carboxylic acid-containing moieties. The (meth)acrylate copolymer includes a first monomer selected from the group consisting of an alkyl acrylate, a substituted alkyl acrylate, an alkyl (meth)acrylate, a substituted alkyl methacrylate and mixtures thereof, and a second monomer selected from the group consisting of an acrylate, a (meth)acrylate or a mixture thereof having an acid cleavable ester substituent; and a photoacid generator. Also disclosed are processes for generating a photoresist image on a substrate with the photoresist composition.Type: ApplicationFiled: August 26, 2009Publication date: March 3, 2011Applicant: International Business Machines CorporationInventors: Robert D. Allen, Phillip J. Brock, Richard A. DiPietro, Hoa D. Truong
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Publication number: 20100062368Abstract: Polymers for use in photoresist compositions include a repeat unit having a formula of: wherein Z represents a repeat unit of a polymer backbone; X is a linking group selected from the group consisting of alkylene, arylene, araalkylene, carbonyl, carboxyl, carboxyalkylene, oxy, oxyalkylene, and combinations thereof, and R is selected from the group consisting of hydrogen, alkyl, aryl, and cycloalkyl groups with the proviso that X and R are not part of the same ring system. Also disclosed are processes for patterning a relief image of the photoresist composition, wherein the photoresist composition has an outgassing rate of less than 6.5E+14 molecules/cm2/s.Type: ApplicationFiled: September 8, 2008Publication date: March 11, 2010Applicant: INTERNATIONAL BUSINESS MACHINES CORPORATIONInventors: Richard A. DiPietro, Ratnam Sooriyakumaran, Sally A. Swanson, Hoa D. Truong
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Patent number: 7563558Abstract: The present invention provides polymers that are useful in negative resist compositions. Polymers of the present invention comprise (1) a first monomer having a polar functional group; (2) a second monomer; and optionally, (3) a third monomer that imparts at least one characteristic selected from crosslinkable functionality, etch resistance, and solubility modulation. The first monomer provides an acid catalyzed polarity switch upon elimination of the polar functional group, whereas, the second monomer provides aqueous dissolution. The polymers of the present invention may be incorporated into negative resist compositions, which may also include photoacid generators, crosslinking agents, basic compounds, solvents, dissolution accelerators, photobase generators, latent basic compounds, surfactants, adhesion promoters, and anti-foaming agents.Type: GrantFiled: October 25, 2007Date of Patent: July 21, 2009Assignee: International Business Machines CorporationInventors: Robert David Allen, Gregory Breyta, Phillip Joe Brock, Richard A. DiPietro, David R. Medeiros, Ratnam Sooriyakumaran
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Patent number: 7465837Abstract: Fluorinated vinyl ethers are provided having the structure of formula (I) the structure of formula (I) wherein at least one of X and Y is a fluorine atom, and L, R1, R2, R3, R4 are as defined herein. Also provided are copolymers prepared by radical polymerization of (I) and a second monomer that may not be fluorinated. The polymers are useful in lithographic photoresist compositions, particularly chemical amplification resists. In a preferred embodiment, the polymers are substantially transparent to deep ultraviolet (DUV) radiation, and are thus useful in DUV lithographic photoresist compositions. A method for using the composition to generate resist images on a substrate is also provided, i.e., in the manufacture of integrated circuits or the like.Type: GrantFiled: August 10, 2006Date of Patent: December 16, 2008Assignee: International Business Machines CorporationInventors: Richard A. DiPietro, Hiroshi Ito
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Publication number: 20080233517Abstract: The present invention provides polymers that are useful in negative resist compositions. Polymers of the present invention comprise (1) a first monomer having a polar functional group; (2) a second monomer; and optionally, (3) a third monomer that imparts at least one characteristic selected from crosslinkable functionality, etch resistance, and solubility modulation. The first monomer provides an acid catalyzed polarity switch upon elimination of the polar functional group, whereas, the second monomer provides aqueous dissolution. The polymers of the present invention may be incorporated into negative resist compositions, which may also include photoacid generators, crosslinking agents, basic compounds, solvents, dissolution accelerators, photobase generators, latent basic compounds, surfactants, adhesion promoters, and anti-foaming agents.Type: ApplicationFiled: October 25, 2007Publication date: September 25, 2008Applicant: International Business Machines CorporationInventors: Robert David Allen, Gregory Breyta, Phillip Joe Brock, Richard A. DiPietro, David R. Medeiros, Ratnam Sooriyakumaran
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Patent number: 7393624Abstract: The present invention provides polymers that are useful in negative resist compositions. Polymers of the present invention comprise (1) a first monomer having a polar functional group; (2) a second monomer; and optionally, (3) a third monomer that imparts at least one characteristic selected from crosslinkable functionality, etch resistance, and solubility modulation. The first monomer provides an acid catalyzed polarity switch upon elimination of the polar functional group, whereas, the second monomer provides aqueous dissolution. The polymers of the present invention may be incorporated into negative resist compositions, which may also include photoacid generators, crosslinking agents, basic compounds, solvents, dissolution accelerators, photobase generators, latent basic compounds, surfactants, adhesion promoters, and anti-foaming agents.Type: GrantFiled: June 20, 2007Date of Patent: July 1, 2008Assignee: International Business Machines CorporationInventors: Robert David Allen, Gregory Breyta, Phillip Joe Brock, Richard A. DiPietro, David R. Medeiros, Ratnam Sooriyakumaran
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Publication number: 20080033202Abstract: The invention provides alkene fluoroalkanol and fluorinated polyol precursors to fluoroalkanol-substituted ?,?-unsaturated esters. The fluoroalkanol-substituted ?,?-unsaturated esters are olefins that can be readily polymerized to provide fluoroalkanol-substituted polymers useful in lithographic photoresist compositions. Also provided are methods for synthesizing the alkene fluoroalkanol and fluorinated polyol precursors.Type: ApplicationFiled: August 24, 2007Publication date: February 7, 2008Applicant: International Business Machines CorporationInventors: Gregory BREYTA, Richard DIPIETRO, Daniel DAWSON
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Publication number: 20080033200Abstract: The invention provides alkene fluoroalkanol and fluorinated polyol precursors to fluoroalkanol-substituted ?,?-unsaturated esters. The fluoroalkanol-substituted ?,?-unsaturated esters are olefins that can be readily polymerized to provide fluoroalkanol-substituted polymers useful in lithographic photoresist compositions. Also provided are methods for synthesizing the alkene fluoroalkanol and fluorinated polyol precursors.Type: ApplicationFiled: August 24, 2007Publication date: February 7, 2008Applicant: International Business Machines CorporationInventors: Gregory Breyta, Richard DiPietro, Daniel Dawson
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Publication number: 20080033198Abstract: The invention provides alkene fluoroalkanol and fluorinated polyol precursors to fluoroalkanol-substituted ?,?-unsaturated esters. The fluoroalkanol-substituted ?,?-unsaturated esters are olefins that can be readily polymerized to provide fluoroalkanol-substituted polymers useful in lithographic photoresist compositions. Also provided are methods for synthesizing the alkene fluoroalkanol and fluorinated polyol precursors.Type: ApplicationFiled: August 24, 2007Publication date: February 7, 2008Applicant: International Business Machines CorporationInventors: Gregory Breyta, Richard Dipietro, Daniel Dawson
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Patent number: 7300739Abstract: The present invention provides polymers that are useful in negative resist compositions. Polymers of the present invention comprise (1) a first monomer having a polar functional group; (2) a second monomer; and optionally, (3) a third monomer that imparts at least one characteristic selected from crosslinkable functionality, etch resistance, and solubility modulation. The first monomer provides an acid catalyzed polarity switch upon elimination of the polar functional group, whereas, the second monomer provides aqueous dissolution. The polymers of the present invention may be incorporated into negative resist compositions, which may also include photoacid generators, crosslinking agents, basic compounds, solvents, dissolution accelerators, photobase generators, latent basic compounds, surfactants, adhesion promoters, and anti-foaming agents.Type: GrantFiled: May 29, 2003Date of Patent: November 27, 2007Assignee: International Business Machines CorporationInventors: Robert David Allen, Gregory Breyta, Phillip Joe Brock, Richard A. DiPietro, David R. Medeiros, Ratnam Sooriyakumaran
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Publication number: 20070259274Abstract: The present invention provides polymers that are useful in negative resist compositions. Polymers of the present invention comprise (1) a first monomer having a polar functional group; (2) a second monomer; and optionally, (3) a third monomer that imparts at least one characteristic selected from crosslinkable functionality, etch resistance, and solubility modulation. The first monomer provides an acid catalyzed polarity switch upon elimination of the polar functional group, whereas, the second monomer provides aqueous dissolution. The polymers of the present invention may be incorporated into negative resist compositions, which may also include photoacid generators, crosslinking agents, basic compounds, solvents, dissolution accelerators, photobase generators, latent basic compounds, surfactants, adhesion promoters, and anti-foaming agents.Type: ApplicationFiled: June 20, 2007Publication date: November 8, 2007Applicant: International Business Machines CorporationInventors: Robert Allen, Gregory Breyta, Phillip Brock, Richard DiPietro, David Medeiros, Ratnam Sooriyakumaran
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Publication number: 20070231734Abstract: A photoresist composition including a polymer, a photo acid generator and a dissolution modification agent, a method of forming an image using the photoresist composition and the dissolution modification agent composition. The dissolution modification agent is insoluble in aqueous alkaline developer and inhibits dissolution of the polymer in the developer until acid is generated by the photoacid generator being exposed to actinic radiation, whereupon the dissolution modifying agent, at a suitable temperature, becomes soluble in the developer and allows the polymer to dissolve in the developer. The DMAs are glucosides, cholates, citrates and adamantanedicarboxylates protected with acid-labile ethoxyethyl, tetrahydrofuranyl, and angelicalactonyl groups.Type: ApplicationFiled: September 29, 2005Publication date: October 4, 2007Inventors: Robert Allen, Phillip Brock, Richard DiPietro, Ratnam Sooriyakumaran, Hoa Truong
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Publication number: 20070051697Abstract: A method of forming an image. The method includes: a transfer layer on a substrate; forming on the transfer layer, an etch barrier layer; pressing a template having a relief pattern into the etch barrier layer; exposing the etch barrier layer to actinic radiation forming a cured etch barrier layer having thick and thin regions corresponding to the relief pattern; removing the template; removing the thin regions of the cured etch barrier layer; removing regions of the transfer layer not protected by the etch barrier layer; removing regions of the substrate not protected by the transfer layer and any remaining etch barrier layer; and removing remaining transfer layer. The transfer layer may be removed using a solvent, the etch barrier layer may include a release agent and an adhesion layer may be formed between the transfer layer and the etch barrier layer. A reverse tone process is also described.Type: ApplicationFiled: September 2, 2005Publication date: March 8, 2007Inventors: Richard DiPietro, Mark Hart, Frances Houle, Hiroshi Ito
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Publication number: 20070026339Abstract: The present invention provides polymers that are useful in negative resist compositions. Polymers of the present invention comprise (1) a first monomer having a polar functional group; (2) a second monomer; and optionally, (3) a third monomer that imparts at least one characteristic selected from crosslinkable functionality, etch resistance, and solubility modulation. The first monomer provides an acid catalyzed polarity switch upon elimination of the polar functional group, whereas, the second monomer provides aqueous dissolution. The polymers of the present invention may be incorporated into negative resist compositions, which may also include photoacid generators, crosslinking agents, basic compounds, solvents, dissolution accelerators, photobase generators, latent basic compounds, surfactants, adhesion promoters, and anti-foaming agents.Type: ApplicationFiled: May 29, 2003Publication date: February 1, 2007Inventors: Robert Allen, Gregory Breyta, Phillip Brock, Richard DiPietro, David Medeiros, Ratnam Sooriyakumaran
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Publication number: 20060287558Abstract: Fluorinated vinyl ethers are provided having the structure of formula (I) the structure of formula (I) wherein at least one of X and Y is a fluorine atom, and L, R1, R2, R3, R4 are as defined herein. Also provided are copolymers prepared by radical polymerization of (I) and a second monomer that may not be fluorinated. The polymers are useful in lithographic photoresist compositions, particularly chemical amplification resists. In a preferred embodiment, the polymers are substantially transparent to deep ultraviolet (DUV) radiation, and are thus useful in DUV lithographic photoresist compositions. A method for using the composition to generate resist images on a substrate is also provided, i.e., in the manufacture of integrated circuits or the like.Type: ApplicationFiled: August 10, 2006Publication date: December 21, 2006Applicant: International Business MachinesInventors: Richard DiPietro, Hiroshi Ito
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Patent number: 7150957Abstract: Fluorinated vinyl ethers are provided having the structure of formula (I) the structure of formula (I) wherein at least one of X and Y is a fluorine atom, and L, R1, R2, R3, R4 are as defined herein. Also provided are copolymers prepared by radical polymerization of (I) and a second monomer that may not be fluorinated. The polymers are useful in lithographic photoresist compositions, particularly chemical amplification resists. In a preferred embodiment, the polymers are substantially transparent to deep ultraviolet (DUV) radiation, and are thus useful in DUV lithographic photoresist compositions. A method for using the composition to generate resist images on a substrate is also provided, i.e., in the manufacture of integrated circuits or the like.Type: GrantFiled: April 25, 2003Date of Patent: December 19, 2006Assignee: International Business Machines CorporationInventors: Richard A. DiPietro, Hiroshi Ito
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Publication number: 20060275701Abstract: Copolymers prepared by copolymerization of at least one fluorinated vinyl ether are provided. In one embodiment, the at least one fluorinated vinyl ether comprises ethylene directly substituted at an olefinic carbon atom with a moiety —OR* and optionally substituted with one, two, or three additional nonhydrogen substituents, wherein R* comprises a fluorinated alkyl moiety substituted with a protected or unprotected hydroxyl group, and further wherein an atom within R* may be (i) taken together with one of the additional nonhydrogen substituents, if present, or (ii) directly bound to an olefinic carbon atom, to form a ring. The polymers are useful, for example, in lithographic photoresist compositions, particularly chemical amplification resists. In a preferred embodiment, the polymers are substantially transparent to deep ultraviolet (DUV) radiation, and are thus useful in DUV lithographic photoresist compositions.Type: ApplicationFiled: August 7, 2006Publication date: December 7, 2006Applicant: International Business MachinesInventors: Richard DiPietro, Hiroshi Ito