US 12,247,039 B2
Organometallic compound, organic light-emitting device including organometallic compound and electronic apparatus including the organic light-emitting device
Minsik Min, Suwon-si (KR); Hyejin Bae, Suwon-si (KR); Soonok Jeon, Suwon-si (KR); Inkoo Kim, Suwon-si (KR); Jong Soo Kim, Hanam-si (KR); Sungho Nam, Daegu (KR); and Hyeonho Choi, Seoul (KR)
Assigned to SAMSUNG ELECTRONICS CO., LTD., Gyeonggi-Do (KR)
Filed by Samsung Electronics Co., Ltd., Suwon-si (KR)
Filed on Nov. 25, 2020, as Appl. No. 17/104,051.
Claims priority of application No. 10-2019-0154355 (KR), filed on Nov. 27, 2019; and application No. 10-2020-0159546 (KR), filed on Nov. 25, 2020.
Prior Publication US 2021/0171548 A1, Jun. 10, 2021
Int. Cl. H01L 51/00 (2006.01); C07F 1/10 (2006.01); C07F 15/00 (2006.01); H10K 85/30 (2023.01); H10K 85/60 (2023.01); H10K 50/15 (2023.01); H10K 50/16 (2023.01)
CPC C07F 1/10 (2013.01) [C07F 15/0066 (2013.01); H10K 85/346 (2023.02); H10K 85/371 (2023.02); H10K 85/631 (2023.02); H10K 50/15 (2023.02); H10K 50/16 (2023.02)] 12 Claims
OG exemplary drawing
 
1. An organometallic compound represented by Formula 1:

OG Complex Work Unit Chemistry
wherein,
M in Formula 1 is Pt,
a bond between X1 and M and a bond between X4 and M in Formula 1 are each a coordinate bond and a bond between X2 and M and a bond between X3 and M in Formula 1 are each a covalent bond,
the group represented by

OG Complex Work Unit Chemistry
in Formula 1 is represented by one of Formulae CY1-26 to CY1-41 or one of Formulae CY1-Z46 to CY1-Z61,

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry
wherein, in Formulae CY1-26 to CY1-1-41 and Formulae CY1-Z46 to CY1-Z61,
X1 is C,
* indicates a binding site to M in Formula 1, and
*′ indicates a binding site to T3 in Formula 1,
ring CY2 is a benzene group represented by Formula CY2(1),

OG Complex Work Unit Chemistry
wherein, in Formula CY2(1),
X2 is C,
*′ indicates a binding site to T3 in Formula 1,
* indicates a binding site to M in Formula 1, and
* ″ indicates a binding site to T1 in Formula 1,
ring CY3 is a carbazole group represented by Formula CY3(1),

OG Complex Work Unit Chemistry
wherein, in Formula CY3(1),
X3 is C,
X31 is a single bond,
*″ indicates a binding site to T1 in Formula 1,
* indicates a binding site to M in Formula 1, and
*′ indicates a binding site to T2 in Formula 1,
ring CY4 is a pyridine group represented by Formula CY4(1),

OG Complex Work Unit Chemistry
wherein, in Formula CY4(1),
X4 is N,
* indicates a binding site to M in Formula 1, and
*′ indicates a binding site to T2 in Formula 1,
n1 to n3 in Formula 1 are each 1,
T1 in Formula 1 is *—S—*′ or *—O—*′,
T2 in Formula 1 is a single bond,
T3 in Formula 1 is a single bond,
n4 in Formula 1 is 0 and T4 is not present,
R11 in Formulae CY1-26 to CY1-41 is a phenyl group substituted with a C1-C60 alkyl group, a deuterated C1-C60 alkyl group, or any combination thereof,
R12 to R15 in Formulae CY1-26 to CY1-41 and CY1-Z46 to CY1-Z61, R2 in Formula 1 and R4 in Formula 1 are each independently hydrogen, deuterium, a C1-C60 alkyl group, or a deuterated C1-C60 alkyl group,
R3 in Formula 1 is:
hydrogen, deuterium, a C1-C60 alkyl group, or a deuterated C1-C60 alkyl group, or
a phenyl group unsubstituted or substituted with deuterium, a C1-C60 alkyl group, a deuterated C1-C60 alkyl group, or any combination thereof,
a2 to a4 in Formula 1 are each independently an integer from 0 to 3,
Z11 in Formulae CY1-Z46 to CY1-Z61 and Z2 to Z4 in Formula 1 are each independently a group represented by Formula 2:

OG Complex Work Unit Chemistry
one of Q51 to Q53 in Formula 2 is a benzene group unsubstituted or substituted with deuterium, a C1-C60 alkyl group, a deuterated C1-C60 alkyl group, or any combination thereof,
two of Q51 to Q53 in Formula 2 are each independently —CH3, —CD3, —CD2H, or —CDH2,
L1 in Formula 2 is a single bond or a benzene group,
c1 in Formula 2 is 1,
c2 in Formula 2 is 1 or 2,
* in Formula 2 indicates a binding site to an adjacent atom,
b2 to b4 in Formula 1 are each 0 or 1,
(a) or (b) is true:
(a) when the group represented by

OG Complex Work Unit Chemistry
in Formula 1 is represented by one of Formulae CY1-26 to CY1-41, then the sum of b2 to b4 in Formula 1 is 1, L1 in Formula 2 is a single bond, and c2 in Formula 2 is 1,
(b) when the group represented by

OG Complex Work Unit Chemistry
in Formula 1 is represented by one of Formulae CY1-Z46 to CY1-Z61, then b2 to b4 in Formula 1 are each 0, L1 in Formula 2 is a benzene group, and c2 in Formula 2 is 1 or 2.