US 12,421,449 B2
Compound and organic light emitting device comprising same
Seonwoo Kim, Daejeon (KR); Wanpyo Hong, Daejeon (KR); Sujeong Geum, Daejeon (KR); Moung Gon Kim, Daejeon (KR); and Kyunghee Kim, Daejeon (KR)
Assigned to LG CHEM, LTD., Seoul (KR)
Appl. No. 17/609,472
Filed by LG CHEM, LTD., Seoul (KR)
PCT Filed Sep. 18, 2020, PCT No. PCT/KR2020/012610
§ 371(c)(1), (2) Date Nov. 8, 2021,
PCT Pub. No. WO2021/107359, PCT Pub. Date Jun. 3, 2021.
Claims priority of application No. 10-2019-0156843 (KR), filed on Nov. 29, 2019.
Prior Publication US 2022/0263027 A1, Aug. 18, 2022
Int. Cl. C07F 5/02 (2006.01); C09K 11/06 (2006.01); H10K 85/30 (2023.01); H10K 85/60 (2023.01); H10K 50/11 (2023.01); H10K 101/10 (2023.01); H10K 101/30 (2023.01)
CPC C09K 11/06 (2013.01) [C07F 5/027 (2013.01); H10K 85/322 (2023.02); H10K 85/658 (2023.02); C07B 2200/05 (2013.01); C09K 2211/1018 (2013.01); H10K 50/11 (2023.02); H10K 2101/10 (2023.02); H10K 2101/30 (2023.02)] 17 Claims
 
1. A compound of any one of the following Chemical Formulae 1-3 to 1-26:

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry
wherein in Chemical Formulae 1-3 to 1-26:
X1 is O;
A1 is an aromatic hydrocarbon ring or a hetero ring;
at least one of A2 and A3 is a hetero ring comprising S or O, and the other is an aromatic hydrocarbon ring;
when each of A2 and A3 is a hetero ring comprising S or O, A2 and A3 are the same as or different from each other;
A4 is an alkyl group, a cycloalkyl group, an aryl group, or a heterocyclic group;
adjacent two or more of A1 to A4 are optionally bonded to each other to form a substituted or unsubstituted ring;
R1 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted heterocyclic group, or a group of the following Chemical Formula 2, or is bonded to an adjacent group to form a substituted or unsubstituted ring;
R2 to R4 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a cyano group; a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkylthioxy group, a substituted or unsubstituted arylthioxy group, a substituted or unsubstituted haloalkoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, or a group of the following Chemical Formula 2, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring;
r1 to r4 are each an integer from 1 to 15;
when r1 to r4 are each 2 to 15, two or more substituents in the parentheses are the same as or different from each other;
R12, R13, R22, R23, R32, R33, R42, and R43 are the same as each other, and are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted haloalkoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or the group of Chemical Formula 2, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring;
r12 and r13 are each 1 or 2;
r22, r23, r32, and r33 are each an integer from 1 to 4;
r42 and r43 are each an integer from 1 to 6;
when r12 and r13 are each 2, two structures in the parentheses are the same as or different from each other;
when r22, r23, r32, r33, r42, and r43 are each 2 or higher, two or more structures in the parentheses are the same as or different from each other;
X and X′ are the same as or different from each other, and are each independently O or S;
A′2 and A′3 are the same as or different from each other, and are each independently an aromatic hydrocarbon ring;

OG Complex Work Unit Chemistry
wherein in Chemical Formula 2:
B1 and B2 are the same as or different from each other, and are each independently an alkyl group, a cycloalkyl group, an aryl group, or a heterocyclic group;
R6 and R7 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted haloalkoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring;
r6 and r7 are each an integer from 1 to 10;
when r6 and r7 are each 2 to 10, two or more substituents in the parentheses are the same as or different from each other; and
at least one hydrogen at a substitutable position of any one of the Chemical Formulae 1-3 to 1-26 is substituted with deuterium.