US 11,987,561 B2
Resist underlayer composition, and method of forming patterns using the composition
Yoojeong Choi, Suwon-si (KR); Soonhyung Kwon, Suwon-si (KR); Hyeon Park, Suwon-si (KR); Jaeyeol Baek, Suwon-si (KR); Minsoo Kim, Suwon-si (KR); Shinhyo Bae, Suwon-si (KR); Daeseok Song, Suwon-si (KR); and Dowon Ahn, Suwon-si (KR)
Assigned to Samsung SDI Co., Ltd., Yongin-si (KR)
Filed by Samsung SDI Co., Ltd., Yongin-si (KR)
Filed on Jan. 12, 2021, as Appl. No. 17/147,308.
Claims priority of application No. 10-2020-0006770 (KR), filed on Jan. 17, 2020.
Prior Publication US 2021/0230127 A1, Jul. 29, 2021
Int. Cl. C07D 251/34 (2006.01); G03F 7/004 (2006.01); G03F 7/11 (2006.01); G03F 7/16 (2006.01); G03F 7/26 (2006.01)
CPC C07D 251/34 (2013.01) [G03F 7/0045 (2013.01); G03F 7/11 (2013.01); G03F 7/168 (2013.01); G03F 7/26 (2013.01)] 17 Claims
OG exemplary drawing
 
1. A resist underlayer composition, comprising:
(A) a polymer comprising a structural unit represented by Chemical Formula 1, a compound represented by Chemical Formula 2, or a combination thereof;
(B) a polymer comprising a structure in which at least one moiety represented by Chemical Formula 3 or Chemical Formula 4, and a moiety represented by Chemical Formula 7 are bound to each other; and
(C) a solvent:

OG Complex Work Unit Chemistry
wherein, in Chemical Formula 1,
R1 and R2 are each independently a hydroxy group, a substituted or unsubstituted C1 to C20 alkoxy group, a halogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C6 to C30 heteroaryl group, a substituted or unsubstituted vinyl group, or a combination thereof,
L1 and L2 are each independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C1 to C20 heteroalkylene group, a substituted or unsubstituted C2 to C20 heterocycloalkylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof, and
* is a linking point;

OG Complex Work Unit Chemistry
wherein, in Chemical Formula 2,
R3 to R6 are each independently a hydroxy group, a thiol group, a cyano group, a substituted or unsubstituted amino group, a halogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof, and
L3 is a single bond, a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C6 to C30 arylene group, or a combination thereof;

OG Complex Work Unit Chemistry
wherein, in Chemical Formulae 3 and 4,
Ra and Rb are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C2 to C20 vinyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C1 to C10 heteroalkyl group, a substituted or unsubstituted C2 to C20 heteroalkenyl group, a substituted or unsubstituted C3 to C20 heterocycloalkyl group, or a substituted or unsubstituted C6 to C20 heteroaryl group, or a combination thereof,
Rc is a terminal group that is a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C2 to C20 alkynyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C10 heteroalkyl group, a substituted or unsubstituted C2 to C20 heteroalkenyl group, a substituted or unsubstituted C3 to C20 heterocycloalkyl group, a structural unit represented by Chemical Formula 5 or Chemical Formula 6, or a combination thereof, and
the at least one moiety represented by Chemical Formula 3 or 4 is linked to * in Chemical Formula 7 at each * position;

OG Complex Work Unit Chemistry
wherein, in Chemical Formulae 5 and 6,
L3 and L4 are each independently a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C1 to C20 heteroalkylene group, or a combination thereof,
Ra and Rb are each independently the same as defined in Chemical Formula 3 and Chemical Formula 4, and
* is a linking point; and

OG Complex Work Unit Chemistry
wherein, in Chemical Formula 7,
A is a single bond, a substituted or unsubstituted C1 to C10 alkylene group, —C(═O)—, —(CO)O—, —O(CO)O—, or a combination thereof,
X is a single bond, —O—, —S—, —S(═O)—, —S(═O)2—, —C(═O)—, —(CO)O—, —O(CO)O—, —NR— (wherein R is hydrogen, deuterium, or a C1 to C10 alkyl group), or a combination thereof,
Rd is hydrogen, deuterium, a halogen, a hydroxy group, a cyano group, a nitro group, an amino group, an epoxy group, a vinyl group, a (meth)acrylate group, an oxetane group, a thiol group, a carboxyl group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C1 to C10 alkoxy group, a substituted or unsubstituted C3 to C10 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C6 to C30 aryloxy group, or a combination thereof,
Re is one of hydrogen, deuterium, or a C1 to C10 alkyl group,
n1 is 2 to 10,000, and
* is linked to Chemical Formula 3 or Chemical Formula 4, or linked to hydrogen, deuterium, a halogen, a hydroxy group, a cyano group, a nitro group, an amino group, an epoxy group, a vinyl group, a (meth)acrylate group, an oxetane group, a thiol group, a carboxyl group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, a substituted or unsubstituted C1 to C10 alkoxy group, a substituted or unsubstituted C3 to C10 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C6 to C30 aryloxy group, or a combination thereof,
provided that at least one of Chemical Formula 3 or Chemical Formula 4 is linked to * of Chemical Formula 7.