Patents by Inventor Robert David Allen
Robert David Allen 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: 7358029Abstract: A photoresist composition including a polymer, a photoacid 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: GrantFiled: September 29, 2005Date of Patent: April 15, 2008Assignee: International Business Machines CorporationInventors: Robert David Allen, Phillip Joe Brock, Richard Anthony DiPietro, Ratnam Sooriyakumaran, Hoa D. Truong
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Publication number: 20070275324Abstract: The present invention relates to a radiation sensitive photoresist composition. The composition comprises a polymer comprising at least two monomers. The first monomer has an acid cleavable tertiary ester group. The second monomer is an acidic monomer. The acid cleavable ester group of the polymer has a surprisingly low activation energy which results in improved resist images in lithographic processes.Type: ApplicationFiled: May 26, 2006Publication date: November 29, 2007Inventors: Robert David Allen, Richard Anthony DiPietro, Ratnam Sooriyakumaran, Hoa D. Truong
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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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Patent number: 7288362Abstract: A topcoat material for applying on top of a photoresist material is disclosed. The topcoat material comprises at least one solvent and a polymer which has a dissolution rate of at least 3000 ?/second in aqueous alkaline developer. The polymer contains a hexafluoroalcohol monomer unit comprising one of the following two structures: wherein n is an integer. The topcoat material may be used in lithography processes, wherein the topcoat material is applied on a photoresist layer. The topcoat material is preferably insoluble in water, and is therefore particularly useful in immersion lithography techniques using water as the imaging medium.Type: GrantFiled: February 23, 2005Date of Patent: October 30, 2007Assignee: International Business Machines CorporationInventors: Robert David Allen, Phillip Joe Brock, Dario Gil, William Dinan Hinsberg, Carl Eric Larson, Linda Karin Sundberg, Gregory Michael Wallraff
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Publication number: 20070238317Abstract: A method of forming low dielectric contrast structures by imprinting a silsesquioxane based polymerizable composition. The imprinting composition including: one or more polyhedral silsesquioxane oligomers each having one or more polymerizable groups, wherein each of the one or more polymerizable group is bound to a different silicon atom of the one or more polyhedral silsesquioxane oligomers; and one or more polymerizable diluents, the diluents constituting at least 50% by weight of the composition.Type: ApplicationFiled: April 5, 2006Publication date: October 11, 2007Applicant: International Business Machines CorporationInventors: Robert David Allen, Richard Anthony DiPietro, Geraud Jean-Michel Dubois, Mark Whitney Hart, Robert Dennis Miller, Ratnam Sooriyakumaran
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Patent number: 7261992Abstract: Fluorocarbinol- and/or fluoroacid-functionalized silsesquioxane polymers and copolymers are provided. The polymers are substantially transparent to ultraviolet radiation (UV), i.e., radiation of a wavelength less than 365 nm and are also substantially transparent to deep ultraviolet radiation (DUV), i.e., radiation of a wavelength less than 250 nm, including 157 nm, 193 nm and 248 nm radiation, and are thus useful in single and bilayer, positive and negative, lithographic photoresist compositions, providing improved sensitivity and resolution. A process 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: February 19, 2002Date of Patent: August 28, 2007Assignee: International Business Machines CorporationInventors: Ratnam Sooriyakumaran, Robert David Allen, Debra Fenzel-Alexander
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Patent number: 7193023Abstract: Polymers containing an acetal or ketal linkage and their use in lithographic photoresist compositions, particularly in chemical amplification photoresists, are provided. The polymer is prepared from at least one first olefinic monomer containing an acetal or ketal linkage, the acid-catalyzed cleavage of which renders the polymer soluble in aqueous base; and at least one second olefinic monomer selected from (i) an olefinic monomer containing a pendant fluorinated hydroxyalkyl group RH, (ii) an olefinic monomer containing a pendant fluorinated alkylsulfonamide group RS, and (iii) combinations thereof. The acetal or ketal linkage may be contained within an acid-cleavable substituent RCL in the first olefinic monomer. A method for using the photoresist compositions containing these polymers in preparing a patterned substrate is also provided in which the polymer is rendered soluble in aqueous base at a temperature of less than about 100° C.Type: GrantFiled: December 4, 2003Date of Patent: March 20, 2007Assignee: International Business Machines CorporationInventors: Robert David Allen, Gregory Breyta, Phillip Joe Brock, Richard Anthony DiPietro, Ratnam Sooriyakumaran, Hoa D. Truong, Gregory Michael Wallraff
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Patent number: 7141692Abstract: A nonpolymeric silsesquioxane is provided wherein at least one silicon atom of the silsesquioxane is directly or indirectly bound to an acid-cleavable substituent RCL. The silsesquioxane has a glass transition temperature Tg of greater than 50° C., and the RCL substituent can be cleaved from the silsesquioxane at a temperature below Tg, generally at least 5° C. below Tg. The remainder of the silicon atoms within the silsesquioxane structure may be bound to additional acid-cleavable groups, acid-inert polar groups RP, and/or acid-inert nonpolar groups RNP. The nonpolymeric silsesquioxane can be a polyhedral silsesquioxane optionally having one to three open vertices, such that the polyhedron appears to be a “partial cage” structure, or a macromer of two to four such polyhedral silsesquioxanes. Photoresist compositions containing the novel nonpolymeric silsesquioxanes are also provided, as is a method for using the compositions in preparing a patterned substrate.Type: GrantFiled: November 24, 2003Date of Patent: November 28, 2006Assignee: International Business Machines CorporationInventors: Robert David Allen, Wu-Song Huang, Mahmoud Khojasteh, Qinghuang Lin, Dirk Pfeiffer, Ratnam Sooriyakumaran, Hoa D. Truong
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Patent number: 7135595Abstract: A photoresist composition is provided that includes a polymer having at least one acrylate or methacrylate monomer having a formula where R1 represents hydrogen (H), a linear or branched alkyl group of 1 to 20 carbons, or a semi- or perfluorinated linear or branched alkyl group of 1 to 20 carbons; and where R2 represents an unsubstituted aliphatic group or a substituted aliphatic group having zero or one trifluoromethyl (CF3) group attached to each carbon of the substituted aliphatic group, or a substituted or unsubstituted aromatic group; and where R3 represents hydrogen (H), methyl (CH3), trifluoromethyl (CF3), difluoromethyl (CHF2), fluoromethyl (CH2F), or a semi- or perfluorinated aliphatic chain; and where R4 represents trifluoromethyl (CF3), difluoromethyl (CHF2), fluoromethyl (CH2F), or a semi- or perfluorinated substituted or unsubstituted aliphatic group. A method of patterning a substrate using the photoresist composition is also provided herein.Type: GrantFiled: January 12, 2006Date of Patent: November 14, 2006Assignee: International Business Machines CorporationInventors: Robert David Allen, Gregory Breyta, Phillip Brock, Richard A. DiPietro, Debra Fenzel-Alexander, Carl Larson, David R. Medeiros, Dirk Pfeiffer, Ratnam Sooriyakumaran, Hoa D. Truong, Gregory M. Wallraff
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Patent number: 7014980Abstract: A photoresist composition is provided that includes a polymer having at least one acrylate or methacrylate monomer having a formula where R1 represents hydrogen (H), a linear or branched alkyl group of 1 to 20 carbons, or a semi- or perfluorinated linear or branched alkyl group of 1 to 20 carbons; and where R2 represents an unsubstituted aliphatic group or a substituted aliphatic group having zero or one trifluoromethyl (CF3) group attached to each carbon of the substituted aliphatic group, or a substituted or unsubstituted aromatic group; and where R3 represents hydrogen (H), methyl (CH3), trifluoromethyl (CF3), difluoromethyl(CHF2), fluoromethyl (CH2F), or a semi- or perfluorinated aliphatic chain; and where R4 represents trifluoromethyl (CF3), difluoromethyl (CHF2), fluoromethyl (CH2F), or a semi- or perfluorinated substituted or unsubstituted aliphatic group. A method of patterning a substrate using the photoresist composition is also provided herein.Type: GrantFiled: August 12, 2004Date of Patent: March 21, 2006Assignee: International Business Machines CorporationInventors: Robert David Allen, Gregory Breyta, Phillip Brock, Richard A. DiPietro, Debra Fenzel-Alexander, Carl Larson, David R. Medeiros, Dirk Pfeiffer, Ratnam Sooriyakumaran, Hoa D. Truong, Gregory M. Wallraff
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Patent number: 6806026Abstract: A photoresist composition is provided that includes a polymer having at least one acrylate or methacrylate monomer having a formula: where R1 represents hydrogen (H), a linear or branched alkyl group of 1 to 20 carbons, or a semi- or perfluorinated linear or branched alkyl group of 1 to 20 carbons; and where R2 represents an unsubstituted aliphatic group or a substituted aliphatic group having zero or one trifluoromethyl (CF3) group attached to each carbon of the substituted aliphatic group, or a substituted or unsubstituted aromatic group; and where R3 represents hydrogen (H), methyl (CH3), trifluoromethyl (CF3), difluoromethyl (CHF2), fluoromethyl (CH2F), or a semi- or perfluorinated aliphatic chain; and where R4 represents trifluoromethyl (CF3), difluoromethyl (CHF2), fluoromethyl (CH2F), or a semi- or perfluorinated substituted or unsubstituted aliphatic group. A method of patterning a substrate using the photoresist composition is also provided herein.Type: GrantFiled: May 31, 2002Date of Patent: October 19, 2004Assignee: International Business Machines CorporationInventors: Robert David Allen, Gregory Breyta, Phillip Brock, Richard A. DiPietro, Debra Fenzel-Alexander, Carl Larson, David R. Medeiros, Dirk Pfeiffer, Ratnam Sooriyakumaran, Hoa D. Truong, Gregory M. Wallraff
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Patent number: 6794459Abstract: The present invention relates to cyclic polymers and their use in photolithographic applications. The cyclic polymers contain a pendant acid labile functional group and a functional group containing a protected hydroxyl moiety. The polymers are post modified by deprotecting the pendant hydroxyl moiety and reacting the deprotected hydroxyl containing moiety with a coreactant. The post-functionalized polymers find application in chemically amplified photoresist compositions.Type: GrantFiled: August 21, 2002Date of Patent: September 21, 2004Assignees: Sumitomo Bakelite Co., Ltd., International Business Machines Corp.Inventors: Saikumar Jayaraman, George Martin Benedikt, Larry Funderburk Rhodes, Richard Vicari, Robert David Allen, Richard Anthony DiPietro, Ratnam Sooriyakumaran, Thomas Wallow
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Patent number: 6723486Abstract: The present invention relates to a radiation sensitive photoresist composition comprising a photoacid initiator and a polycyclic polymer comprising repeating units that contain pendant acid labile groups. Upon exposure to an imaging radiation source the photoacid initiator generates an acid which cleaves the pendant acid labile groups effecting a polarity change in the polymer. The polymer is rendered soluble in an aqueous base in the areas exposed to the imaging source.Type: GrantFiled: May 8, 2001Date of Patent: April 20, 2004Assignees: Sumitomo Bakelite Co., Ltd., International Business Machines Corp.Inventors: Brian L. Goodall, Saikumar Jayaraman, Robert A. Shick, Larry F. Rhodes, Robert David Allen, Richard Anthony DiPietro, Thomas Wallow
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Publication number: 20030224283Abstract: A photoresist composition is provided that includes a polymer having at least one acrylate or methacrylate monomer having a formula 1Type: ApplicationFiled: May 31, 2002Publication date: December 4, 2003Applicant: International Business Machines CorporationInventors: Robert David Allen, Gregory Breyta, Phillip Brock, Richard A. DiPietro, Debra Fenzel-Alexander, Carl Larson, David R. Medeiros, Dirk Pfeiffer, Ratnam Sooriyakumaran, Hoa D. Truong, Gregory M. Wallraff
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Patent number: 6610456Abstract: Copolymers prepared by radical polymerization of a fluorine-containing aromatic monomer and an acrylate-based comonomer that may or 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, i.e., radiation of a wavelength less than 250 nm, including 157 nm and 248 nm 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: February 26, 2001Date of Patent: August 26, 2003Assignee: International Business Machines CorporationInventors: Robert David Allen, Phillip Joe Brock, Hiroshi Ito, Gregory Michael Wallraff
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Patent number: 6525153Abstract: Polymers comprising polycyclic repeating units containing pendant anhydride moieties are disclosed. The polymer can be polymerized from polycycloolefins containing pendant anhydride moieties in the presence of a nickel containing single component catalyst. In optional embodiments the polycycloolefin monomer containing the pendant anhydride functionality can be copolymerized with other polycycloolefin monomers that contain pendant functional groups to yield random copolymer products.Type: GrantFiled: March 9, 2000Date of Patent: February 25, 2003Assignees: Sumitomo Bakelite Co., Ltd., International Business Machines Corp.Inventors: Saikumar Jayaraman, Brian L. Goodall, Richard Vicari, John-Henry Lipian, Robert David Allen, Juliann Opitz, Thomas I. Wallow
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Publication number: 20030018153Abstract: The present invention relates to cyclic polymers and their use in photolithographic applications. The cyclic polymers contain a pendant acid labile functional group and a functional group containing a protected hydroxyl moiety.Type: ApplicationFiled: August 21, 2002Publication date: January 23, 2003Applicant: The B.F.Goodrich CompanyInventors: Saikumar Jayaraman, George Martin Benedikt, Larry Funderburk Rhodes, Richard Vicari, Robert David Allen, Richard Anthony DiPetro, Ratnam Sooriyakumaran, Thomas Wallow
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Publication number: 20020164538Abstract: Copolymers prepared by radical polymerization of a fluorine-containing aromatic monomer and an acrylate-based comonomer that may or 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, i.e., radiation of a wavelength less than 250 nm, including 157 nm and 248 nm 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: February 26, 2001Publication date: November 7, 2002Applicant: International Business Machines CorporationInventors: Robert David Allen, Phillip Joe Brock, Hiroshi Ito, Gregory Michael Wallraff
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Patent number: 6451499Abstract: Polycyclic polymers containing pendant aromatic moieties are disclosed. The polymers exhibit light transparency properties to deep UV wave lengths making them useful for high resolution photolithographic applications. These polymers are particularly useful in chemically amplified positive and negative tone resists.Type: GrantFiled: June 27, 2000Date of Patent: September 17, 2002Assignees: The B.F. Goodrich Company, International Business Machines Corp.Inventors: Saikumar Jayaraman, Brian Leslie Goodall, Larry Funderburk Rhodes, Robert Adam Shick, Richard Vicari, Robert David Allen, Juliann Opitz, Ratnam Sooriyakumaran, Thomas Wallow
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Patent number: RE38282Abstract: The invention relates to a process for forming bilayer resist images with a chemically-amplified, radiation-sensitive bilayer resist. The bilayer resist is disposed on a substrate and comprises (i) a top imaging layer comprising a radiation-sensitive acid generator and a vinyl polymer having an acid-cleavable silylethoxy group and (ii) an organic underlayer. The bilayer resist is used in the manufacture of integrated circuits.Type: GrantFiled: June 28, 2001Date of Patent: October 21, 2003Assignee: International Business Machines CorporationInventors: Robert David Allen, Donald Clifford Hofer, Ratnam Sooriyakumaran, Gregory Michael Wallraff