US 12,287,576 B2
Underlayer compositions and patterning methods
Joshua Kaitz, Watertown, MA (US); Sheng Liu, Bow, NH (US); Li Cui, Westborough, MA (US); Shintaro Yamada, Shrewsbury, MA (US); James F. Cameron, Brookline, MA (US); Emad Aqad, Northborough, MA (US); Iou-Sheng Ke, Andover, MA (US); and Suzanne M. Coley, Mansfield, MA (US)
Assigned to DUPONT ELECTRONIC MATERIALS INTERNATIONAL, LLC, Marlborough, MA (US)
Filed by DuPont Electronic Materials International, LLC, Marlborough, MA (US)
Filed on Jun. 20, 2024, as Appl. No. 18/748,270.
Application 18/748,270 is a continuation of application No. 17/007,903, filed on Aug. 31, 2020, abandoned.
Prior Publication US 2024/0337946 A1, Oct. 10, 2024
Int. Cl. G03F 7/11 (2006.01); C08G 8/04 (2006.01); C09D 161/06 (2006.01)
CPC G03F 7/11 (2013.01) [C08G 8/04 (2013.01); C09D 161/06 (2013.01)] 20 Claims
 
1. An underlayer composition, comprising a polymer comprising a repeating unit of formula (1):

OG Complex Work Unit Chemistry
wherein, Ar is a monocyclic or polycyclic C5-60 aromatic group, wherein the aromatic group comprises one or more aromatic ring heteroatoms, a substituent group comprising a heteroatom, or a combination thereof;
X is C or O;
R1 is 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;
R2 is substituted or unsubstituted C4-30 alkyl, 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, substituted or unsubstituted C4-30 heteroarylalkyl, or —NR11R12, wherein R11 to R12 are each independently hydrogen, substituted or unsubstituted C1-30 alkyl, substituted or unsubstituted C3-30 cycloalkyl, substituted or unsubstituted C2-30 heterocycloalkyl, substituted or unsubstituted C6-30 aryl, substituted or unsubstituted C7-30 arylalkyl, substituted or unsubstituted C3-30 heteroaryl, or substituted or unsubstituted C4-30 heteroarylalkyl;
optionally, R1 and R2 can be taken together form a 5- to 7-membered carbocyclic ring;
optionally, one of R11 to R12 can be taken together with R1 to form a 5- to 7-membered ring;
when X is C, Ra and Rb 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;
wherein Ra and Rb optionally may be taken together to form a 5- to 7-membered ring;
wherein one of Ra or Rb optionally may be taken together with R2 to form a 5- to 7-membered ring which is not an aromatic ring; and
when X is O, Ra and Rb are absent,
provided that Ar comprises a group of formula (2), formula (3a), formula (3b), or formula (3c) when the repeating unit of formula (1) is represented by formulae (11) or (12),

OG Complex Work Unit Chemistry
wherein, in formula (2),
A1, A2, and A3 are each present or absent, and each independently represents 1 to 3 fused aromatic rings;
R3 and R4 are each independently 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, halogen, —OR31, —SR32, or —NR33R34;
provided that at least one of R3 or R4 is —OR31, —SR32, or —NR33R34;
R31 to R34 are each independently hydrogen, substituted or unsubstituted C1-30 alkyl, substituted or unsubstituted C3-30 cycloalkyl, substituted or unsubstituted C2-30 heterocycloalkyl, substituted or unsubstituted C6-30 aryl, substituted or unsubstituted C7-30 arylalkyl, substituted or unsubstituted C3-30 heteroaryl, or substituted or unsubstituted C4-30 heteroarylalkyl;
m is an integer 0 to 4;
n is an integer 0 to 4; and
provided that the sum of m and n is an integer greater than 0, and wherein, in formulae (3a), (3b), and (3c),
A4 may be present or absent, and represents 1 to 3 fused aromatic rings;
Z1 and Z2 are each independently C or N;
each R5 is independently 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; and
p is an integer of 0 to 4,
wherein A4 comprises at least one heteroaryl ring, at least one of Z1 and Z2 is N, or a combination thereof.