Abstract: A copolymer include repeat units derived from an acid-labile monomer, an aliphatic lactone-containing monomer, a C1-12 alkyl(meth)acrylate in which the C1-12 alkyl group includes a specific base-soluble group, a photoacid-generating monomer that includes an aliphatic anion, and a neutral aromatic monomer having the formula wherein R1, R2, R3, X, m, and Ar are defined herein. The copolymer is used as a component of a photoresist composition. A coated substrate including a layer of the photoresist composition, and a method of forming an electronic device using the coated substrate are described.
Type:
Grant
Filed:
October 30, 2014
Date of Patent:
January 5, 2016
Assignee:
ROHM AND HAAS ELECTRONIC MATERIALS LLC
Inventors:
Vipul Jain, Owendi Ongayi, James W. Thackeray, James F. Cameron
Abstract: Disclosed herein is a composition comprising a graft block copolymer comprising a copolymer comprising a backbone polymer; and a first graft polymer that comprises a surface energy reducing moiety; the first graft polymer being grafted onto the backbone polymer; where the surface energy reducing moiety comprises a fluorine atom, a silicon atom, or a combination of a fluorine atom and a silicon atom; a photoacid generator; and a crosslinking agent.
Type:
Grant
Filed:
November 19, 2012
Date of Patent:
December 29, 2015
Assignees:
THE TEXAS A&M UNIVERSITY SYSTEM, ROHM AND HAAS ELECTRONIC MATERIALS LLC
Inventors:
Sangho Cho, Guorong Sun, Karen L. Wooley, James W. Thackeray, Peter Trefonas, III
Abstract: Provided are photoresist overcoat compositions, substrates coated with the overcoat compositions and methods of forming electronic devices by a negative tone development process. The compositions, coated substrates and methods find particular applicability in the manufacture of semiconductor devices.
Type:
Grant
Filed:
December 3, 2014
Date of Patent:
December 15, 2015
Assignee:
Rohm and Haas Electronic Materials LLC
Inventors:
Young Cheol Bae, Rosemary Bell, Jong Keun Park, Seung-Hyun Lee
Abstract: Provided are methods of trimming photoresist patterns. The methods involve coating a photoresist trimming composition over a photoresist pattern, wherein the trimming composition includes a matrix polymer, a thermal acid generator and a solvent, the trimming composition being free of cross-linking agents. The coated semiconductor substrate is heated to generate an acid in the trimming composition from the thermal acid generator, thereby causing a change in polarity of the matrix polymer in a surface region of the photoresist pattern. The photoresist pattern is contacted with a developing solution to remove the surface region of the photoresist pattern. The methods find particular applicability in the formation of very fine lithographic features in the manufacture of semiconductor devices.
Abstract: Provided are gap-fill methods. The methods comprise: (a) providing a semiconductor substrate having a relief image on a surface of the substrate, the relief image comprising a plurality of gaps to be filled; (b) applying a gap-fill composition over the relief image, wherein the gap-fill composition comprises a self-crosslinkable polymer and a solvent, wherein the self-crosslinkable polymer comprises a first unit comprising a polymerized backbone and a crosslinkable group pendant to the backbone; and (c) heating the gap-fill composition at a temperature to cause the polymer to self-crosslink. The methods find particular applicability in the manufacture of semiconductor devices for the filling of high aspect ratio gaps.
Type:
Grant
Filed:
November 14, 2014
Date of Patent:
December 8, 2015
Assignees:
Rohm and Haas Electronic Materials LLC, Dow Global Technologies LLC
Inventors:
Jong Keun Park, Cheng-Bai Xu, Phillip D. Hustad, Mingqi Li
Abstract: A copolymer includes the polymerized product of a comonomer and a monomer having the formula (I): wherein c is 0, 1, 2, 3, 4, or 5; Ra is H, F, —CN, C1-10 alkyl, or C1-10 fluoroalkyl; Rx and Ry are each independently an unsubstituted or substituted C1-10 linear or branched alkyl group, an unsubstituted or substituted C3-10 cycloalkyl group, an unsubstituted or substituted C3-10 alkenylalkyl group, or an unsubstituted or substituted C3-10 alkynylalkyl group; wherein Rx and Ry together optionally form a ring; and Rz is a C6-20 aryl group substituted with an acetal-containing group or a ketal-containing group, or a C3-C20 heteroaryl group substituted with an acetal-containing group or a ketal-containing group, wherein the C6-20 aryl group or the C3-C20 heteroaryl group can, optionally, be further substituted. Also described are a photoresist including the copolymer, a coated substrate having a layer of the photoresist, and a method of forming an electronic device utilizing the photoresist.
Type:
Grant
Filed:
February 21, 2014
Date of Patent:
December 8, 2015
Assignee:
ROHM AND HAAS ELECTRONIC MATERIALS LLC
Inventors:
Owendi Ongayi, James W. Thackeray, James F. Cameron
Abstract: Provided are photoresist compositions useful in forming photolithographic patterns by a negative tone development process. Also provided are methods of forming photolithographic patterns by a negative tone development process and substrates coated with the photoresist compositions. The compositions, methods and coated substrates find particular applicability in the manufacture of semiconductor devices.
Type:
Grant
Filed:
May 31, 2011
Date of Patent:
November 17, 2015
Assignee:
Rohm and Haas Electronic Materials LLC
Inventors:
Young Cheol Bae, Deyan Wang, Thomas Cardolaccia, Seokho Kang, Rosemary Bell
Abstract: A copolymer includes repeat units derived from a lactone-substituted monomer, a base-soluble monomer having a pKa less than or equal to 12, a photoacid-generating monomer, and an acid-labile monomer having the formula wherein R1, R2, R3, and Ar are defined herein. The copolymer can be used as a component of a photoresist composition, and the photoresist composition can be coated on a substrate having one or more layers to be patterned, or used in a method of forming an electronic device.
Type:
Grant
Filed:
October 30, 2014
Date of Patent:
November 10, 2015
Assignee:
ROHM AND HAAS ELECTRONIC MATERIALS LLC
Inventors:
Owendi Ongayi, Vipul Jain, James F. Cameron, James W. Thackeray, Suzanne Coley
Abstract: A copolymer comprising the polymerized product of an electron-sensitizing acid deprotectable monomer, such as the monomer having the formula (XX), and a comonomer: wherein Ra is H, F, —CN, C1-10 alkyl, or C1-10 fluoroalkyl; Rx and Ry are each independently a substituted or unsubstituted C1-10 alkyl group or C3-10 cycloalkyl group; Rz is a substituted or unsubstituted C6-20 aromatic-containing group or C6-20 cycloaliphatic-containing group; wherein Rx and Ry together optionally form a ring; and wherein at least one of Rx, Ry and Rz is halogenated. A photoresist and coated substrate comprising the copolymer, and a method of making an electronic device using the photoresist, are also disclosed.
Abstract: Methods of treating the surface of a metal-containing hardmask used in the manufacture of semiconductors by contacting the hardmask surface with a composition capable of adjusting the water contact angle so as to substantially match that of subsequently applied organic coatings are provided.
Type:
Grant
Filed:
January 19, 2013
Date of Patent:
October 27, 2015
Assignee:
Rohm and Haas Electronic Materials LLC
Inventors:
Deyan Wang, Peter Trefonas, III, Jieqian Zhang, Peng-Wei Chuang
Abstract: Provided are photoresist compositions useful in forming photolithographic patterns by a negative tone development process. Also provided are methods of forming photolithographic patterns by a negative tone development process and substrates coated with the photoresist compositions. The photoresist compositions include one or more polymer additive that contains a basic moiety and which is substantially non-miscible with a resin component of the resist. The compositions, methods and coated substrates find particular applicability in the manufacture of semiconductor devices.
Type:
Grant
Filed:
July 31, 2013
Date of Patent:
October 13, 2015
Assignee:
Rohm and Haas Electronic Materials LLC
Inventors:
Jong Keun Park, Christopher Nam Lee, Cecily Andes, Deyan Wang
Abstract: This invention relates to new photoacid generator compounds and photoresist compositions that comprise such compounds. In particular, the invention relates to photoacid generator compounds that comprise base-cleavable groups.
Abstract: Compositions useful for improving the adhesion of coating compositions, such as dielectric film-forming compositions, include a hydrolyzed amino-alkoxysilane having a protected amino moiety. These compositions are useful in methods of improving the adhesion of coating compositions to a substrate, such as an electronic device substrate.
Type:
Grant
Filed:
March 2, 2015
Date of Patent:
October 6, 2015
Assignee:
Rohm and Haas Electronic Materials LLC
Inventors:
Michael K. Gallagher, Joseph F. Lachowski, Gregory P. Prokopowicz, Zidong Wang
Abstract: Compositions useful for improving the adhesion of coating compositions, such as dielectric film-forming compositions, include a hydrolyzed amino-alkoxysilane having a protected amino moiety. These compositions are useful in methods of improving the adhesion of coating compositions to a substrate, such as an electronic device substrate.
Type:
Application
Filed:
March 27, 2014
Publication date:
October 1, 2015
Applicant:
Rohm and Haas Electronic Materials LLC
Inventors:
Michael K. GALLAGHER, Joseph F. LACHOWSKI, Gregory P. PROKOPOWICZ, Zidong WANG
Abstract: A process for manufacturing silver nanowires is provided, comprising: providing a silver ink core component containing ?60 wt % silver nanoparticles dispersed in a silver carrier; providing a shell component containing a film forming polymer dispersed in a shell carrier; providing a substrate; coelectrospinning the silver ink core component and the shell component depositing on the substrate a core shell fiber having a core and a shell surrounding the core, wherein the silver nanoparticles are in the core; and, treating the silver nanoparticles to form a population of silver nanowires, wherein the population of silver nanowires exhibit an average length, L, of ?60 ?m.
Type:
Grant
Filed:
July 22, 2013
Date of Patent:
September 29, 2015
Assignee:
Rohm and Haas Electronic Materials LLC
Inventors:
Jerome Claracq, Garo Khanarian, Lujia Bu, Jaebum Joo, Peter Trefonas
Abstract: A photoacid generator compound has the formula (I): [A-(CHR1)p]k-(L)-(CH2)m—(C(R2)2)nSO3?Z+??(I) wherein A is a substituted or unsubstituted, monocyclic, polycyclic, or fused polycyclic C5 or greater cycloaliphatic group optionally comprising O, S, N, F, or a combination comprising at least one of the foregoing, R1 is H, a single bond, or a substituted or unsubstituted C1-30 alkyl group, wherein when R1 is a single bond, R1 is covalently bonded to a carbon atom of A, each R2 is independently H, F, or C1-4 fluoroalkyl, wherein at least one R2 is not hydrogen, L is a linking group comprising a sulfonate group, a sulfonamide group, or a C1-30 sulfonate or sulfonamide-containing group, Z is an organic or inorganic cation, p is an integer of 0 to 10, k is 1 or 2, m is an integer of 0 or greater, and n is an integer of 1 or greater.
Type:
Grant
Filed:
November 4, 2014
Date of Patent:
September 29, 2015
Assignee:
ROHM AND HAAS ELECTRONIC MATERIALS LLC
Inventors:
Emad Aqad, Cheng-Bai Xu, Mingqi Li, Shintaro Yamada, William Williams, III
Abstract: Compositions suitable for forming oxymetal hardmask layers are provided. Methods of forming oxymetal hardmask layers using such compositions are also provided, where the surface of the oxymetal hardmask layer formed has a water contact angle substantially matched to that of subsequently applied organic coatings.
Type:
Grant
Filed:
January 19, 2013
Date of Patent:
September 15, 2015
Assignee:
Rohm and Haas Electronic Materials LLC
Inventors:
Deyan Wang, Peter Trefonas, III, Shintaro Yamada, Kathleen M. O'Connell
Abstract: Compositions useful for improving the adhesion of coating compositions, such as dielectric film-forming compositions, include a hydrolyzed amino-alkoxysilane having a protected amino moiety. These compositions are useful in methods of improving the adhesion of coating compositions to a substrate, such as an electronic device substrate.
Type:
Grant
Filed:
March 27, 2014
Date of Patent:
September 15, 2015
Assignee:
Rohm and Haas Electronic Materials LLC
Inventors:
Michael K. Gallagher, Joseph F. Lachowski, Gregory P. Prokopowicz, Zidong Wang
Abstract: Disclosed herein is a block copolymer comprising a first block derived from a vinyl aromatic monomer; and a second block derived from an acrylate monomer; where a chi parameter that measures interactions between the first block and the second block is greater than or equal to about 0.05, when measured at 240° C. Disclosed herein too is a method comprising polymerizing a vinyl aromatic monomer to form a first block; and polymerizing a second block onto the first block to form a block copolymer; where the second block is derived by polymerizing an acrylate monomer; and where the block copolymer has a chi parameter of greater than or equal to about 0.05, when measured at 240° C.; where the chi parameter is a measure of interactions between the first block and the second block.
Type:
Grant
Filed:
May 16, 2012
Date of Patent:
September 8, 2015
Assignees:
ROHM AND HAAS ELECTRONIC MATERIALS LLC, DOW GLOBAL TECHNOLOGIES LLC, UNIVERSITY OF MINNESOTA
Inventors:
Phillip Dene Hustad, Peter Trefonas, III, Frank Steven Bates, Marc Andrew Hillmyer, Justin Glenn Kennemur