US 11,968,884 B2
Organometallic compound, organic light-emitting device including the same, and diagnostic composition including the organometallic compound
Jungin Lee, Hwaseong-si (KR); Kyuyoung Hwang, Anyang-si (KR); Soyeon Kim, Seoul (KR); Aram Jeon, Suwon-si (KR); Hyeonho Choi, Seoul (KR); Hyun Koo, Seoul (KR); Sangdong Kim, Seoul (KR); Yoonhyun Kwak, Seoul (KR); Ohyun Kwon, Seoul (KR); and Byoungki Choi, Hwaseong-si (KR)
Assigned to SAMSUNG ELECTRONICS CO., LTD., Gyeonggi-Do (KR)
Filed by SAMSUNG ELECTRONICS CO., LTD., Suwon-si (KR)
Filed on Sep. 29, 2022, as Appl. No. 17/936,602.
Application 17/936,602 is a continuation of application No. 17/166,385, filed on Feb. 3, 2021, granted, now 11,539,007.
Application 17/166,385 is a continuation of application No. 17/128,400, filed on Dec. 21, 2020, granted, now 11,641,773.
Application 17/128,400 is a continuation of application No. 15/641,299, filed on Jul. 4, 2017, granted, now 10,937,973, issued on Mar. 2, 2021.
Claims priority of application No. 10-2016-0085069 (KR), filed on Jul. 5, 2016.
Prior Publication US 2023/0128713 A1, Apr. 27, 2023
This patent is subject to a terminal disclaimer.
Int. Cl. H10K 85/30 (2023.01); C07F 15/00 (2006.01); C09K 11/06 (2006.01); H10K 50/11 (2023.01); H10K 85/40 (2023.01); H10K 101/10 (2023.01)
CPC H10K 85/346 (2023.02) [C07F 15/0086 (2013.01); C09K 11/06 (2013.01); H10K 85/40 (2023.02); C09K 2211/1044 (2013.01); C09K 2211/185 (2013.01); H10K 50/11 (2023.02); H10K 2101/10 (2023.02)] 20 Claims
 
1. An organometallic compound represented by Formula 1-1:

OG Complex Work Unit Chemistry
wherein, in Formula 1-1,
the moiety represented by

OG Complex Work Unit Chemistry
 is represented by Formula CY2-1:

OG Complex Work Unit Chemistry
*′ indicates a binding site to M of Formula 1-1,
* indicates a binding site to a neighboring atom of Formula 1-1, and
*″ indicates a binding site to a neighboring atom of Formula 1-1
M is platinum (Pt),
X1 is O,
X2 is N,
X3 is C,
X51 is N-[(L7)b7-(R7)],
X11 is C—(R11), X12 is C—(R12), X13 is C—(R13), X14 is C—(R14),
X21 is C—(R21), X22 is C—(R22), X23 is C—(R23),
X31 is C—(R31), X32 is C—(R32), X33 is C—(R33),
X41 iS C—(R41), X42 iS C-[(L42)b42-(R42)c42], X43 iS C—(R43), X44 is C—(R44),
L42 and L7 are each independently a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group,
b42 is an integer from 0 to 5,
b7 is an integer from 1 to 5,
c42 is an integer from 1 to 5,
R7, R11 to R14, R21 to R23, R31 to R33 and R41 to R44 are each independently selected from hydrogen, deuterium, —F, a cyano group, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C1-C60 heteroaryl group, —N(Q1)(Q2), and —Si(Q3)(Q4)(Q5),
the substituent of the substituted C5-C30 carbocyclic group, the substituted C1-C30 heterocyclic group, the substituted C1-C60 alkyl group, the substituted C6-C60 aryl group and the substituted C1-C60 heteroaryl group is selected from:
deuterium, —F, a cyano group, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2;
a C1-C60 alkyl group, a C1-C60 alkyl group substituted with at least one selected from deuterium, —F, a cyano group, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a C6-C60 aryl group, and a C1-C60 heteroaryl group;
a C6-C60 aryl group, a C6-C60 aryl group substituted with at least one selected from deuterium, —F, a cyano group, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, C1-C60 alkyl group, a C6-C60 aryl group, and a C1-C60 heteroaryl group;
a C1-C60 heteroaryl group, a C1-C60 heteroaryl group substituted with at least one selected from deuterium, —F, a cyano group, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, C1-C60 alkyl group, a C6-C60 aryl group, and a C1-C60 heteroaryl group; and
—N(Q31)(Q32), and —Si(Q33)(Q34)(Q35); and
Q1 to Q5 and Q31 to Q35 are each independently selected from hydrogen, deuterium, —F; a C1-C60 alkyl group, a C1-C60 alkyl group substituted with at least one selected from deuterium, —F, and a C6-C60 aryl group; a C6-C60 aryl group and a C6-C60 aryl group substituted with at least one selected from deuterium, —F, and a C1-C60 alkyl group.