US 12,240,863 B2
Organometallic compound, organic light-emitting device including the same, and electronic apparatus including the organic light-emitting device
Ohyun Kwon, Seoul (KR); Aram Jeon, Seoul (KR); Sangho Park, Anyang-si (KR); Virendra Kumar Rai, Hwaseong-si (KR); Myungsun Sim, Suwon-si (KR); Sukekazu Aratani, Hwaseong-si (KR); Kum Hee Lee, Suwon-si (KR); Banglin Lee, Suwon-si (KR); Sunghun Lee, Hwaseong-si (KR); Byoungki Choi, Hwaseong-si (KR); and Yasushi Koishikawa, 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, 2020, as Appl. No. 17/036,694.
Claims priority of application No. 10-2020-0015840 (KR), filed on Feb. 10, 2020.
Prior Publication US 2021/0253618 A1, Aug. 19, 2021
Int. Cl. C07F 15/00 (2006.01); C09K 11/06 (2006.01); H10K 50/11 (2023.01); H10K 50/12 (2023.01); H10K 50/14 (2023.01); H10K 50/15 (2023.01); H10K 50/16 (2023.01); H10K 85/30 (2023.01); H10K 85/40 (2023.01); H10K 30/30 (2023.01); H10K 50/17 (2023.01)
CPC C07F 15/0033 (2013.01) [H10K 85/342 (2023.02); H10K 30/353 (2023.02); H10K 50/15 (2023.02); H10K 50/16 (2023.02); H10K 50/171 (2023.02)] 14 Claims
 
1. An organometallic compound represented by Formula 1:
M(L1)n1(L2)n2  Formula 1
wherein, in Formula 1,
M is Ir,
L1 is a ligand represented by Formulae 2-1, 2-2, or 2-3,
n1 is 1, 2, or 3, wherein, when n1 is 2 or greater, two or more ligands L1 are identical to or different from each other,
L2 is a ligand represented by Formula 3D,
n2 is 0, 1, or 2, wherein, when n2 is 2, two or more ligands L2 are identical to or different from each other, and
a sum of n1 and n2 is 3,

OG Complex Work Unit Chemistry
wherein, in Formulae 2-1 to 2-3,
X11 is N, or C(R11),
X12 is N, or C(R12),
X13 is N, or C(R13),
X14 is N, or C(R14),
X1 is O, S, or C(R31)(R32),
X2 is O, S, or C(R33)(R34),
Y1 is N, Y2 is C,
ring CY1 is a phenyl group, a pyridine group, or a pyrimidine group,
ring CY2 is a phenyl group, a naphthalene group, a fluorene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, or a dibenzosilole group,
with the proviso that when L1 is the ligand represented by Formula 2-3, then X12 is C(R12), and R12 is —Si(Q3)(Q4)(Q5) or —Ge(Q3)(Q4)(Q5),
R1, R2, R11, R13, and R14 are each independently hydrogen, deuterium, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, or a substituted or unsubstituted C6-C60 aryl group,
R12, and R31 to R34 are each independently hydrogen, deuterium, —F, —C1, —Br, —I, —SF5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group 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 C7-C60 alkylaryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C7-C60 arylalkyl group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted C1-C60 heteroaryloxy group, a substituted or unsubstituted C1-C60 heteroarylthio group, a substituted or unsubstituted C2-C60 heteroarylalkyl group, a substituted or unsubstituted C2-C60 alkylheteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q1)(Q2), —Si(Q3)(Q4)(Q5), —Ge(Q3)(Q4)(Q5), —B(Q6)(Q7), —P(═O)(Q8)(Q9), or —P(Q8)(Q9), wherein R31 and R33 are not hydrogen,
a1 is an integer of 0 to 4, wherein, when a1 is 2 or greater, two or more groups R1 are identical to or different from each other,
a2 is an integer of 0 to 8, wherein, when a2 is 2 or greater, two or more groups R2 are identical to or different from each other,
provided that the organometallic compound does not comprise a compound wherein n2 in Formula 1 is 0, X1 is C(R31)(R32), and X2 is C(R33)(R34),
two or more of a plurality of groups R1 are optionally linked together to form 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,
two or more of a plurality of groups R2 are optionally linked together to form 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,
R10a is the same as described in connection with R2,
* and *′ in each indicate a binding site to M in Formula 1,

OG Complex Work Unit Chemistry
wherein, in Formula 3D,
T21 is a single bond,
Y11 is N,
Y12 is C,
ring CY11 is a pyridine group or a pyrimidine group,
ring CY12 is a benzene group, a naphthalene group, a fluorene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, or a dibenzosilole group,
d1 to d2 are each independently an integer from 0 to 10,
Z1 and Z2 are the same as described in connection with R2,
* and *′ in Formula 3D each indicate a binding site to Min Formula 1,
substituents of the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, the substituted C1-C60 alkoxy group, the substituted C3-C10 cycloalkyl group, the substituted C1-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C1-C10 heterocycloalkenyl group, the substituted C6-C60 aryl group, the substituted C7-C60 alkylaryl group, the substituted C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C7-C60 arylalkyl group, the substituted C1-C60 heteroaryl group, the substituted C1-C60 heteroaryloxy group, the substituted C1-C60 heteroarylthio group, the substituted C2-C60 heteroarylalkyl group, the substituted C2-C60 alkylheteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group are each independently:
deuterium, —F, —C1, —Br, —I, -CD3, -CD2H, -CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, an unsubstituted C1-C60 alkyl group, an unsubstituted C2-C60 alkenyl group, an unsubstituted C2-C60 alkynyl group, or an unsubstituted C1-C60 alkoxy group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group, each substituted with at least one of deuterium, —F, —C1, —Br, —I, -CD3, -CD2H, -CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C7-C60 alkylaryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a C2-C60 heteroarylalkyl group, a C2-C60 alkylheteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q11)(Q12), —Si(Q13)(Q14)(Q15), —Ge(Q13)(Q14)(Q15), —B(Q16)(Q17), —P(═O)(Q18)(Q19), or —P(Q18)(Q19);
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with at least one of deuterium, —F, —C1, —Br, —I, -CD3, -CD2H, -CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C7-C60 alkylaryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a C2-C60 heteroarylalkyl group, a C2-C60 alkylheteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q21)(Q22), —Si(Q23)(Q24)(Q25), —Ge(Q23)(Q24)(Q25), —B(Q26)(Q27), —P(═O)(Q28)(Q29), or —P(Q28)(Q29);
—N(Q31)(Q32), —Si(Q33)(Q34)(Q35), —Ge(Q33)(Q34)(Q35), —B(Q36)(Q37), —P(═O)(Q38)(Q39), or —P(Q38)(Q39); or
a combination thereof, and
Q1 to Q9, Q11 to Q19, Q21 to Q29, and Q31 to Q39 are each independently hydrogen;
deuterium; —F; —C1; —Br; —I; a hydroxyl group; a cyano group; a nitro group; an amidino group; a hydrazine group; a hydrazone group; a carboxylic acid group or a salt thereof; a sulfonic acid group or a salt thereof; a phosphoric acid group or a salt thereof; a C1-C60 alkyl group which is unsubstituted or substituted with at least one of deuterium, a C1-C60 alkyl group, or a C6-C60 aryl group; a C2-C60 alkenyl group; a C2-C60 alkynyl group; a C1-C60 alkoxy group; a C3-C10 cycloalkyl group; a C1-C10 heterocycloalkyl group; a C3-C10 cycloalkenyl group; a C1-C10 heterocycloalkenyl group; a C6-C60 aryl group which is unsubstituted or substituted with at least one of deuterium, a C1-C60 alkyl group, or a C6-C60 aryl group; a C6-C60 aryloxy group; a C6-C60 arylthio group; a C7-C60 arylalkyl group; a C1-C60 heteroaryl group; a C1-C60 heteroaryloxy group; a C1-C60 heteroarylthio group; a C2-C60 heteroarylalkyl group; a C2-C60 alkylheteroaryl group; a monovalent non-aromatic condensed polycyclic group; or a monovalent non-aromatic condensed heteropolycyclic group.