US 12,250,879 B2
Heterocyclic compound and organic light emitting device comprising the same
Su Jin Han, Daejeon (KR); Dong Hoon Lee, Daejeon (KR); Boon Jae Jang, Daejeon (KR); Wanpyo Hong, Daejeon (KR); Min Woo Jung, Daejeon (KR); Jungha Lee, Daejeon (KR); Seulchan Park, Daejeon (KR); and Sunghyun Hwang, Daejeon (KR)
Assigned to LG CHEM, LTD., Seoul (KR)
Appl. No. 17/274,878
Filed by LG CHEM, LTD., Seoul (KR)
PCT Filed Sep. 20, 2019, PCT No. PCT/KR2019/012236
§ 371(c)(1), (2) Date Mar. 10, 2021,
PCT Pub. No. WO2020/060286, PCT Pub. Date Mar. 26, 2020.
Claims priority of application No. 10-2018-0114411 (KR), filed on Sep. 21, 2018; and application No. 10-2019-0115650 (KR), filed on Sep. 19, 2019.
Prior Publication US 2022/0059773 A1, Feb. 24, 2022
Int. Cl. C07D 405/14 (2006.01); C07D 409/14 (2006.01); C07D 487/04 (2006.01); C07D 491/048 (2006.01); C07D 495/04 (2006.01); H10K 85/60 (2023.01); H10K 50/11 (2023.01); H10K 50/15 (2023.01); H10K 50/16 (2023.01); H10K 50/17 (2023.01)
CPC H10K 85/654 (2023.02) [C07D 405/14 (2013.01); C07D 409/14 (2013.01); C07D 487/04 (2013.01); C07D 491/048 (2013.01); C07D 495/04 (2013.01); H10K 85/6572 (2023.02); H10K 85/6574 (2023.02); H10K 85/6576 (2023.02); H10K 50/11 (2023.02); H10K 50/15 (2023.02); H10K 50/16 (2023.02); H10K 50/17 (2023.02); H10K 50/171 (2023.02)] 8 Claims
 
1. A compound of Chemical Formula 1:
Chemical Formula 1

OG Complex Work Unit Chemistry
wherein, in Chemical Formula 1:
X is O or S;
Y1, Y2 and Y3 are each independently CH or N, provided that at least one of Y1, Y2 and Y3 is N;
L1 and L2 are each independently a direct bond, a substituted or unsubstituted C6-60 arylene, or a substituted or unsubstituted C5-60 heteroarylene containing at least one heteroatom selected from the group consisting of N, O and S;
Ar1 is a substituted or unsubstituted C6-60 aryl;
Ar2 and Ar3 are each independently any one selected from the group consisting of the following:

OG Complex Work Unit Chemistry
wherein in the above formulas:
a′ is an integer from 0 to 4;
b′ is an integer from 0 to 5;
c′ is an integer from 0 to 7;
d′ is an integer from 0 to 8;
e′ is an integer from 0 to 9; and
f is an integer from 0 to 11,
provided that when Ar1 is any one selected from the group consisting of the following:

OG Complex Work Unit Chemistry
wherein in the above formulas:
a is an integer from 0 to 4;
b is an integer from 0 to 5;
c is an integer from 0 to 7;
d is an integer from 0 to 9; and
e is an integer from 0 to 11,
and Ar2 and Ar3 are each independently any one selected from the group consisting of the following:

OG Complex Work Unit Chemistry
wherein in the above formulas:
a′ is an integer from 0 to 4;
b′ is an integer from 0 to 5;
c′ is an integer from 0 to 7;
d′ is an integer from 0 to 8;
e′ is an integer from 0 to 9; and
f′ is an integer from 0 to 11,
any one of Ar1, Ar2 and Ar3 is substituted with 4 or more deuteriums;
each R1 is independently hydrogen, deuterium, halogen, or a substituted or unsubstituted C1-60 alkyl;
each R2 is independently hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted C1-60 alkyl, a substituted or unsubstituted C1-60 alkoxy, a substituted or unsubstituted C3-60 cycloalkyl, a substituted or unsubstituted C1-60 haloalkyl, a substituted or unsubstituted C1-60 haloalkoxy, a substituted or unsubstituted C6-60 arylamine, a substituted or unsubstituted C1-60 alkylamine, a substituted or unsubstituted C1-60 trifluoroalkyl, a substituted or unsubstituted C1-60 trifluoroalkoxy, a substituted or unsubstituted C6-60 aryl, or a substituted or unsubstituted C5-60 heteroaryl containing at least one of N, O and S, or R2 can bond with carbon atoms of the carbazole to form a condensed ring;
m is an integer from 0 to 3;
n is an integer from 0 to 6; and
l is 1 or 2.