US 12,082,492 B2
Organometallic compound and organic light-emitting device including the same
Kum Hee Lee, Suwon-si (KR); Ohyun Kwon, Yongin-si (KR); Kyuyoung Hwang, Anyang-si (KR); Yoonhyun Kwak, Seoul (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 Jun. 24, 2021, as Appl. No. 17/356,785.
Application 17/356,785 is a continuation of application No. 14/953,091, filed on Nov. 27, 2015, abandoned.
Claims priority of application No. 10-2014-0169185 (KR), filed on Nov. 28, 2014; and application No. 10-2015-0103013 (KR), filed on Jul. 21, 2015.
Prior Publication US 2022/0123236 A1, Apr. 21, 2022
Int. Cl. H10K 85/40 (2023.01); C07F 15/00 (2006.01); C09K 11/02 (2006.01); C09K 11/06 (2006.01); H10K 50/11 (2023.01); H10K 85/60 (2023.01); H10K 101/40 (2023.01)
CPC H10K 85/40 (2023.02) [C07F 15/0033 (2013.01); C09K 11/025 (2013.01); C09K 11/06 (2013.01); H10K 85/6572 (2023.02); C09K 2211/1007 (2013.01); C09K 2211/1011 (2013.01); C09K 2211/1029 (2013.01); C09K 2211/185 (2013.01); H10K 50/11 (2023.02); H10K 2101/40 (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 Ir,
L1 in Formula 1 is selected from ligands represented by Formula 2(1),
n1 is 1, 2, or 3, provided that when n1 is 2 or greater, two or more groups L1 are identical to or different from each other,
L2 in Formula 1 is selected from ligands represented by Formula 3A,
n2 is 0, 1, or 2, provided that when n2 is 2 or greater, two or more groups L2 are identical to or different from each other,
L1 and L2 in Formula 1 are different from each other,
the sum of n1 and n2 is 3,
CY1 in Formula 2(1) is a triphenylene,
Y11 in Formula 3A is N,
Y12 to Y14 in Formula 3A is C,
CY3 in Formula 3A is selected from a pyridine, a 5,6,7,8-tetrahydroquinoline, a 5,6,7,8-tetrahydroisoquinoline, a quinoline, and an isoquinoline,
CY4 in Formula 3A is selected from a benzene, 1,2,3,4-tetrahydronaphthalene, a naphthalene, a carbazole, an azacarbazole, a fluorene, a dibenzofuran, a dibenzothiophene, a benzofuropyridine, and a benzothienopyridine,
a1 and a2 in Formula 3A are each independently an integer selected from 1 to 5,
R1 to R6 in Formula 2(1) are each independently selected from:
a hydrogen, deuterium, —F, C1-C20 alkyl group, and a C1-C20 alkoxy group; and
a C1-C20 alkyl group and a C1-C20 alkoxy group, each substituted with at least one selected from deuterium, —F, —CD3, —CD2H, —CDH2, —CF3, —CF2H, and —CFH2;
Z1 and Z2 in Formula 3A are each independently selected from:
hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, a hydroxyl group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, and a phosphoric acid or a salt thereof;
a C1-C20 alkyl group and a C1-C20 alkoxy group, each substituted with at least one selected from deuterium, —F, —CD3, —CD2H, —CDH2, —CF3, —CF2H, and —CFH2; and
a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q1)(Q2)(Q3), —N(Q4)(Q5), —B(Q6)(Q7), and —P(═O)(Q8)(Q9),
R11 and R12 in Formula 2 are each independently selected from:
deuterium, —F, —Cl, —Br, —I, —SF5, a hydroxyl group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, and a phosphoric acid or a salt thereof;
a C1-C20 alkyl group and a C1-C20 alkoxy group, each substituted with at least one selected from deuterium, —F, —CD3, —CD2H, —CDH2, —CF3, —CF2H, and —CFH2; and
a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q4)(Q5), —B(Q6)(Q7), and —P(═O)(Q8)(Q9),
b1 in Formula 2(1) is selected from 0 to 3,
b2 in Formula 2(1) is selected from 0 to 4,
each of * and *′ in Formulae 2(1) and 3A indicates a binding site to M in Formula 1, and
at least one of substituents of the substituted C3-C10 cycloalkyl group, substituted C1-C10 heterocycloalkyl group, substituted C3-C10 cycloalkenyl group, substituted C1-C10 heterocycloalkenyl group, substituted C6-C60 aryl group, substituted C6-C60 aryloxy group, substituted C6-C60 arylthio group, substituted C1-C60 heteroaryl group, substituted monovalent non-aromatic condensed polycyclic group, and substituted monovalent non-aromatic condensed heteropolycyclic group is selected from deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group and a phenyl group,
wherein Q1 to Q9 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.