US 11,947,258 B2
Photoacid-generating monomer, polymer derived therefrom, photoresist composition including the polymer, and method of forming a photoresist relief image using the photoresist composition
Emad Aqad, Northborough, MA (US); James W. Thackeray, Braintree, MA (US); and James F. Cameron, Brookline, MA (US)
Assigned to ROHM AND HASS ELECTRONIC MATERIALS LLC, Marlborough, MA (US)
Filed by ROHM AND HAAS ELECTRONIC MATERIALS LLC, Marlborough, MA (US)
Filed on Feb. 24, 2023, as Appl. No. 18/174,316.
Application 18/174,316 is a division of application No. 15/131,135, filed on Apr. 18, 2016, granted, now 11,613,519.
Application 15/131,135 is a continuation in part of application No. 15/055,911, filed on Feb. 29, 2016, abandoned.
Prior Publication US 2023/0212112 A1, Jul. 6, 2023
Int. Cl. G03F 7/004 (2006.01); C07C 303/32 (2006.01); C07C 309/06 (2006.01); C07C 309/07 (2006.01); C07C 309/12 (2006.01); C07C 309/17 (2006.01); C07C 309/20 (2006.01); C07C 309/23 (2006.01); C07C 309/42 (2006.01); C08F 222/18 (2006.01); C08F 222/24 (2006.01); C08F 224/00 (2006.01); C08F 228/02 (2006.01); G03F 7/039 (2006.01); G03F 7/30 (2006.01)
CPC G03F 7/0045 (2013.01) [C07C 303/32 (2013.01); C07C 309/06 (2013.01); C07C 309/07 (2013.01); C07C 309/12 (2013.01); C07C 309/17 (2013.01); C07C 309/20 (2013.01); C07C 309/23 (2013.01); C07C 309/42 (2013.01); C08F 224/00 (2013.01); G03F 7/0397 (2013.01)] 20 Claims
 
1. A polymer comprising repeat units derived from a monomer having a structure

OG Complex Work Unit Chemistry
wherein,
R is an organic group consisting of (A) a polymerizable carbon-carbon double bond or carbon-carbon triple bond group selected from the group consisting of C2-12 alkenyl, C2-12 alkynyl, acryloyl, 2-(C1-12-alkyl)acryloyl, 2-(C1-12-fluoroalkyl)acryloyl, 2-cyanoacryloyl, and 2-fluoroacryloyl, and (B) one or more divalent groups selected from a straight chain or branched non-fluorinated C1-20 alkylene group, a monocyclic or polycyclic non-fluorinated C3-20 cycloalkylene group, a monocyclic or polycyclic C3-20 heterocycloalkylene group, a monocyclic or polycyclic C6-20 arylene group, a monocyclic or polycyclic C1-20 heteroarylene group, and a combination thereof;
wherein the C1-20 alkylene group, C3-20 cycloalkylene group, the monocyclic or polycyclic C3-20 heterocycloalkylene group, the monocyclic or polycyclic C6-20 arylene group, and the monocyclic or polycyclic C1-20 heteroarylene group are optionally substituted with at least one monovalent substituent selected from chlorine, bromine, iodine, hydroxyl, amino, thiol, carboxyl, carboxylate, amide, nitrile, nitro, C1-18 alkyl, C1-18 alkoxyl, C6-18 aryl, C6-18 aryloxyl, C7-18 alkylaryl, or C7-18 alkylaryloxyl;
X and Y are independently at each occurrence hydrogen or a non-fluorinated non-hydrogen substituent;
EWG1 and EWG2 are independently at each occurrence an electron-withdrawing group;
p is 1, 2, 3, or 4;
n is 2, 3, or 4; and
M+ is an organic cation.
 
9. A photoresist composition, comprising the polymer of claim 1.