US 12,085,854 B2
Photoresist compositions and pattern formation methods
Cong Liu, Shrewsbury, MA (US); Jong Keun Park, Shrewsbury, MA (US); James F. Cameron, Brookline, MA (US); Sheng Liu, Bow, NH (US); Tsutomu Asazuma, Agano (JP); and Mingqi Li, Shrewsbury, MA (US)
Assigned to ROHM AND HAAS ELECTRONIC MATERIALS LLC, Marlborough, MA (US)
Filed by ROHM AND HAAS ELECTRONIC MATERIALS LLC, Marlborough, MA (US)
Filed on Sep. 30, 2021, as Appl. No. 17/490,738.
Prior Publication US 2023/0104130 A1, Apr. 6, 2023
Int. Cl. G03F 7/038 (2006.01); G03F 7/004 (2006.01); G03F 7/039 (2006.01)
CPC G03F 7/0045 (2013.01) [G03F 7/038 (2013.01); G03F 7/039 (2013.01)] 18 Claims
 
1. A photoresist composition, comprising:
a polymer;
a photoacid generator;
an additive of Formula (1a); and
a solvent:

OG Complex Work Unit Chemistry
wherein, in Formula (1a),
R1 and R2 are each independently substituted or unsubstituted C1-4 alkyl, substituted or unsubstituted C1-20 heteroalkyl, substituted or unsubstituted C3-20 cycloalkyl, substituted or unsubstituted C3-20 heterocycloalkyl, substituted or unsubstituted C6-20 aryl, or substituted or unsubstituted C3-20 heteroaryl;
each of R1 and R2 optionally further comprises as part of their structure one or more groups selected from —O—, —C(O)—, —S—, —S(O)2—, and —N(R1a)—, wherein R1a is hydrogen, substituted or unsubstituted C1-20 alkyl, substituted or unsubstituted C3-20 cycloalkyl, or substituted or unsubstituted C3-20 heterocycloalkyl;
R3a and R3b are each independently hydrogen, substituted or unsubstituted C1-20 alkyl, substituted or unsubstituted C3-20 cycloalkyl, substituted or unsubstituted C1-20 heteroalkyl, substituted or unsubstituted C3-20 heterocycloalkyl, substituted or unsubstituted C6-20 aryl, or substituted or unsubstituted C3-20 heteroaryl; wherein the substituted C1-20 alkyl is substituted with nitro, cyano, hydroxyl, carboxylic acid or an alkali metal or ammonium salt thereof, halogen, thiol, C1-6 alkylthio, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 haloalkyl, C1-9 alkoxy, C1-6 haloalkoxy, C3-12 cycloalkyl, C5-18 cycloalkenyl, C2-18 heterocycloalkenyl, C6-12 aryl, C7-19 arylalkyl, C7-12 alkylaryl, C3-12 heterocycloalkyl, C3-12 heteroaryl, or a combination thereof; and wherein the C1-20 heteroalkyl and the C3-12 heterocycloalkyl each independently has a heteroatom selected from O, S, Si, P, or a combination thereof;
each R4 is independently substituted or unsubstituted C1-20 alkyl, substituted or unsubstituted C1-20 heteroalkyl, substituted or unsubstituted C3-20 cycloalkyl, substituted or unsubstituted C3-20 heterocycloalkyl, substituted or unsubstituted C6-20 aryl, or substituted or unsubstituted C3-20 heteroaryl;
each R4 optionally further comprises as part of their structure one or more groups selected from —O—, —C(O)—, —S—, —S(O)2—, and —N(R2a)—, wherein R2a is hydrogen, substituted or unsubstituted C1-20 alkyl, substituted or unsubstituted C3-20 cycloalkyl, or substituted or unsubstituted C3-20 heterocycloalkyl;
R1 and R2 together optionally form a ring via a single bond or a divalent linking group;
any two of R3a, R3b, or R4 together optionally form a ring via a single bond or a divalent linking group;
when n is 2 or greater, any two R4 groups together optionally form a ring via a single bond or a divalent linking group;
m is an integer from 1 to 5; and
n is an integer from 0 to 2m.