US 12,379,660 B2
Adhesion promoting photoresist underlayer composition
Joshua Kaitz, Watertown, MA (US); Ke Yang, Westborough, MA (US); Keren Zhang, Kirkland, WA (US); Li Cui, Westborough, MA (US); James F. Cameron, Brookline, MA (US); Dan B. Millward, Ukiah, CA (US); and Shintaro Yamada, Shrewsbury, MA (US)
Assigned to DUPONT ELECTRONIC MATERIALS INTERNATIONAL, LLC, Marlborough, MA (US)
Filed by ROHM AND HAAS ELECTRONIC MATERIALS LLC, Marlborough, MA (US)
Filed on Dec. 18, 2020, as Appl. No. 17/127,434.
Prior Publication US 2022/0197143 A1, Jun. 23, 2022
Int. Cl. G03F 7/11 (2006.01); C08G 65/40 (2006.01); C08K 5/053 (2006.01); C08K 5/06 (2006.01); C08K 5/09 (2006.01); C08K 5/105 (2006.01); C08K 5/19 (2006.01); C09D 171/00 (2006.01)
CPC G03F 7/11 (2013.01) [C08G 65/4012 (2013.01); C09D 171/00 (2013.01); C08K 5/053 (2013.01); C08K 5/06 (2013.01); C08K 5/09 (2013.01); C08K 5/105 (2013.01); C08K 5/19 (2013.01)] 18 Claims
 
1. A photoresist underlayer composition, comprising:
a poly (arylene ether) derived from a compound containing two or more cyclopentadienone moieties, wherein the compound is free of a solubility enhancing polar moiety;
an additive of formula (14):
D-(L1-Ar—[X]n)m  (14); and
a solvent,
wherein, in formula (14),
D is a substituted or unsubstituted C1-60 organic group, optionally wherein D is an organic acid salt of the substituted or unsubstituted C1-60 organic group;
each L1 is independently a single bond or a divalent linking group,
when L1 is a single bond, D may be a substituted or unsubstituted C3-30 cycloalkyl or substituted or unsubstituted C1-20 heterocycloalkyl that is optionally fused with Ar,
each Ar is independently a monocyclic or polycyclic C5-60 aromatic group,
each X is independently −OR30, −SR31, or −NR32R33,
m is an integer of 1 to 6,
each n is independently an integer of 0 to 5, provided that a sum of all n is 2 or greater,
R30 to R33 are each independently hydrogen, substituted or unsubstituted C1-30 alkyl, substituted or unsubstituted C1-30 heteroalkyl, substituted or unsubstituted C3-30 cycloalkyl, substituted or unsubstituted C2-30 heterocycloalkyl, substituted or unsubstituted C2-30 alkenyl, substituted or unsubstituted C2-30 alkynyl, substituted or unsubstituted C6-30 aryl, substituted or unsubstituted C7-30 arylalkyl, substituted or unsubstituted C7-30 alkylaryl, substituted or unsubstituted C3-30 heteroaryl, or substituted or unsubstituted C4-30 heteroarylalkyl, each of which except hydrogen optionally further comprises as part of its structure one or more of substituted or unsubstituted C1-30 alkylene, substituted or unsubstituted C3-30 cycloalkylene, substituted or unsubstituted C2-30 alkenylene, substituted or unsubstituted C4-30 cycloalkenylene, substituted or unsubstituted C2-30 alkynylene, substituted or unsubstituted C1-30 heterocycloalkylene, substituted or unsubstituted C6-30 arylene, substituted or unsubstituted C4-30 heteroarylene, —O—, —C(O)—, —C(O)O—, —S—, —S(O)—, —S(O)2—, or −NR34— wherein R34 is substituted or unsubstituted C1-30 alkyl, substituted or unsubstituted C3-30 cycloalkyl, substituted or unsubstituted C1-20 heterocycloalkyl, substituted or unsubstituted C6-30 aryl, substituted or unsubstituted C7-30 arylalkyl, substituted or unsubstituted C7-30 alkylaryl, substituted or unsubstituted C4-30 heteroaryl, substituted or unsubstituted C5-30 heteroarylalkyl, or substituted or unsubstituted C5-30 alkylheteroaryl, and
when n is 2, optionally any one of R30 to R33 of a first group X is a divalent group, any one of R30 to R33 of a second group X is a divalent group, and the divalent group of the first group X forms a ring together with the divalent group of the second group X, wherein the ring optionally further comprises a linking group comprising one or more of substituted or unsubstituted C1-30 alkylene, substituted or unsubstituted C3-30 cycloalkylene, substituted or unsubstituted C2-30 alkenylene, substituted or unsubstituted C4-30 cycloalkenylene, substituted or unsubstituted C2-30 alkynylene, substituted or unsubstituted C6-30 arylene, —O—, —C(O)—, —C(O)O—, —NR35—, —S—, —S(O)—, or —S(O)2—, wherein R35 is substituted or unsubstituted C1-30 alkyl, substituted or unsubstituted C3-30 cycloalkyl, substituted or unsubstituted C1-20 heterocycloalkyl, substituted or unsubstituted C6-30 aryl, substituted or unsubstituted C7-30 arylalkyl, substituted or unsubstituted C7-30 alkylaryl, substituted or unsubstituted C4-30 heteroaryl, substituted or unsubstituted C5-30 heteroarylalkyl, or substituted or unsubstituted C5-30 alkylheteroaryl.