US 12,391,715 B2
Organometallic compound, light-emitting device including the same, and electronic apparatus including the light-emitting device
Eunsoo Ahn, Yongin-si (KR); Soobyung Ko, Yongin-si (KR); Sungbum Kim, Yongin-si (KR); Eunyoung Lee, Yongin-si (KR); and Jaesung Lee, Yongin-si (KR)
Assigned to Samsung Display Co., Ltd., Yongin-si (KR)
Filed by Samsung Display Co., Ltd., Yongin-si (KR)
Filed on Sep. 2, 2021, as Appl. No. 17/446,819.
Claims priority of application No. 10-2020-0167831 (KR), filed on Dec. 3, 2020.
Prior Publication US 2022/0177503 A1, Jun. 9, 2022
Int. Cl. B82Y 20/00 (2011.01); B82Y 30/00 (2011.01); C07F 5/02 (2006.01); C07F 7/08 (2006.01); C07F 15/00 (2006.01); C09K 11/06 (2006.01); H10K 50/11 (2023.01); H10K 50/115 (2023.01); H10K 50/12 (2023.01); H10K 50/15 (2023.01); H10K 85/10 (2023.01); H10K 85/30 (2023.01); H10K 85/40 (2023.01); H10K 85/60 (2023.01); H10K 101/00 (2023.01); H10K 101/10 (2023.01); H10K 101/40 (2023.01)
CPC C07F 15/0086 (2013.01) [H10K 85/1135 (2023.02); H10K 85/324 (2023.02); H10K 85/342 (2023.02); H10K 85/346 (2023.02); H10K 85/40 (2023.02); H10K 85/622 (2023.02); H10K 85/624 (2023.02); H10K 85/626 (2023.02); H10K 85/633 (2023.02); H10K 85/636 (2023.02); H10K 85/654 (2023.02); H10K 85/6572 (2023.02); H10K 85/6574 (2023.02); H10K 85/6576 (2023.02); H10K 85/658 (2023.02); B82Y 20/00 (2013.01); H10K 50/11 (2023.02); H10K 50/115 (2023.02); H10K 50/12 (2023.02); H10K 50/15 (2023.02); H10K 2101/10 (2023.02); H10K 2101/40 (2023.02)] 19 Claims
OG exemplary drawing
 
1. An organometallic compound represented by Formula 1:

OG Complex Work Unit Chemistry
wherein, in Formula 1,
M is platinum (Pt), palladium (Pd), gold (Au), nickel (Ni), silver (Ag), or copper (Cu),
X1 to X4 are each independently C or N,
A1 to A4 are each independently a C3-C60 carbocyclic group or a C1-C60 heterocyclic group,
CY1 is a triazine group,
T1 and T2 are each independently a single bond, a double bond, *—N[(L1)c1-(Z11)]—*′, *—B(Z11)—*′, *—P(Z11)—*′, *—C(Z11)(Z12)—*′, *—Si(Z11)(Z12)—*′, *—Ge(Z11)(Z12)—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O)2—*′, *—C(Z11)═*, *═C(Z11)—*′, *—C(Z11)═C(Z12)—*′, *—C(═S)—*′, or *—C≡C—*′, where * and *′ each indicate a binding site to a neighboring atom,
L1 is a single bond, a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a, or a C1-C30 heterocyclic group unsubstituted or substituted with at least one R10a,
c1 is an integer from 0 to 5,
a1 and a2 are each independently an integer from 0 to 3,
R1 to R4, Z11, and Z12 are each independently 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), —N(Q1)(Q2), —B(Q1)(Q2), —C(═O)(Q1), —S(═O)2(Q1), or —P(═O)(Q1)(Q2),
R5 is a substituted or unsubstituted phenyl group,
b1 to b4 are each independently an integer from 0 to 10,
b5 is 1,
two or more of R1 to R4, Z11 and Z12 are optionally linked to form a C5-C30 carbocyclic group unsubstituted or substituted with at least one R10a or a C2-C30 heterocyclic group unsubstituted or substituted with at least one R10a,
R10a is:
deuterium (-D), —F, —Cl, —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 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 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-Coo 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: 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; or a C3-C60 carbocyclic group or a C1-C60 heterocyclic group, each 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.