US 12,459,961 B2
Heterocyclic compound, a light-emitting device including the same, and an electronic apparatus including the light-emitting device
Hyojeong Kim, Yongin-si (KR); and Jungsub Lee, Yongin-si (KR)
Assigned to Samsung Display Co., Ltd., Yongin-si (KR)
Filed by Samsung Display Co., Ltd., Yongin-si (KR)
Filed on Aug. 26, 2021, as Appl. No. 17/458,219.
Claims priority of application No. 10-2020-0177437 (KR), filed on Dec. 17, 2020.
Prior Publication US 2022/0209143 A1, Jun. 30, 2022
Int. Cl. C07F 7/08 (2006.01); C07F 5/02 (2006.01); H10K 50/11 (2023.01); H10K 85/40 (2023.01); H10K 85/60 (2023.01)
CPC C07F 7/0805 (2013.01) [C07F 5/027 (2013.01); C07F 7/0812 (2013.01); H10K 85/40 (2023.02); H10K 85/658 (2023.02); H10K 50/11 (2023.02)] 16 Claims
OG exemplary drawing
 
1. A heterocyclic compound of Formula 1-1:

OG Complex Work Unit Chemistry
wherein, in Formula 1-1,
X1 is B,
EW1 is a triazine group unsubstituted or substituted with at least one R10a,
a1 is an integer from 1 to 5,
L1 is a single bond; or a C3-C60 carbocyclic group or a C1-C60 heterocyclic group each, independently from one another, unsubstituted or substituted with at least one R10a, and R1a and R2a are not linked to each other to form a ring,
R1 and R2 are optionally linked to each other via T2 to form a C8-C60 polycyclic group unsubstituted or substituted with at least one R10a,
R3 and R4 are optionally linked to each other via T3 to form a C8-C60 polycyclic group unsubstituted or substituted with least one R10a,
R1 and R3 are not linked to each other to form a ring,
R1 and R4 are not linked to each other to form a ring,
R2 and R3 are not linked to each other to form a ring,
R2 and R4 are not linked to each other to form a ring,
R1 to R4, Z1, and Z2 are each, independently from one another, hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkenyl group unsubstituted or substituted with at least one R10a, a C2-C60 alkynyl group unsubstituted or substituted with at least one R10a, a C1-C60 alkoxy group unsubstituted or substituted with at least one R10a, a C3-C60 carbocyclic group unsubstituted or substituted with at least one R10a, a C1-C60 heterocyclic group unsubstituted or substituted with at least one R10a, a C6-C60 aryloxy group unsubstituted or substituted with at least one R10a, a C6-C60 arylthio group unsubstituted or substituted with at least one R10a, —Si(Q1)(Q2)(Q3), —B(Q1)(Q2), —P(Q1)(Q2), or —C(═O)(Q1),
* and *′ each indicate a binding site to a neighboring atom, and
R10a is:
deuterium, —F, —CI, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group each, independently from one another, unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, —Si(Q11)(Q12)(Q13), —N(Q11)(Q12), —B(Q11)(Q12), —C(═O)(Q11), —S(═O)2(Q11), —P(═O)(Q11)(Q12), or any combination thereof;
a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, or a C6-C60 arylthio group each, independently from one another, unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C60 carbocyclic group, a C1-C60 heterocyclic group, a C6-C60 aryloxy group, a C6-C60 arylthio group, —Si(Q21)(Q22)(Q23), —N(Q21)(Q22), —B(Q21)(Q22), —C(═O)(Q21), —S(═O)2(Q21), —P(═O)(Q21)(Q22), or any combination thereof; or
—Si(Q31)(Q32)(Q33), —N(Q31)(Q32), —B(Q31)(Q32), —C(═O)(Q31), —S(═O)2(Q31), or —P(═O)(Q31)(Q32),
wherein Q1 to Q3, Q11 to Q13, Q21 to Q23, and Q31 to Q33 are each, independently from one another: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C1-C60 alkyl group; a C2-C60 alkenyl group; a C2-C60 alkynyl group; a C1-C60 alkoxy group; a C3-C60 carbocyclic group or a C1-C60 heterocyclic group each, independently from one another, unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof,
b11 is an integer from 0 to 4,
R1a and R2a are each, independently from one another: hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C1-C20 alkyl group, a C1-C20 alkoxy group, or a phenyl group; or
a C1-C20 alkyl group, a C1-C20 alkoxy group, or a phenyl group each, independently from one another, unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, a C1-C10 alkyl group, a C1-C20 alkoxy group, a phenyl group, or any combination thereof,
R1 and a phenylene group between Si and X1 are optionally linked to each other via T1 to form a C8-C60 polycyclic group unsubstituted or substituted with at least one R10a,
T1 to T3 are each, independently from one another, a single bond, *—O—*′, *—S—*′, *—C(═O)—*′, *—N(Z1)—*′, *—C(Z1)(Z2)—*′, *—C(Z1)═C(Z2)—*′, *—C(Z1)═*′, or *═C(Z1)═*′,
c14 and c24 are each, independently from one another, an integer from 0 to 4.