US 12,490,646 B2
Organic light-emitting device
Yongsik Jung, Seoul (KR); Youngmin You, Seoul (KR); Seunga Heo, Seoul (KR); Joonghyuk Kim, Seoul (KR); Hyeonho Choi, Seoul (KR); Inkoo Kim, Suwon-si (KR); and Hyejin Bae, Suwon-si (KR)
Assigned to SAMSUNG ELECTRONICS CO., LTD., Gyeonggi-Do (KR); and EWHA UNIVERSITY—INDUSTRY COLLABORATION FOUNDATION, Seoul (KR)
Filed by Samsung Electronics Co., Ltd., Suwon-si (KR); and Ewha University—Industry Collaboration Foundation, Seoul (KR)
Filed on Feb. 22, 2022, as Appl. No. 17/677,381.
Claims priority of application No. 10-2021-0125203 (KR), filed on Sep. 17, 2021.
Prior Publication US 2023/0137127 A1, May 4, 2023
Int. Cl. H01L 51/54 (2006.01); C07F 1/00 (2006.01); C09K 11/06 (2006.01); H10K 85/30 (2023.01); H10K 50/12 (2023.01); H10K 101/00 (2023.01)
CPC H10K 85/371 (2023.02) [C07F 1/00 (2013.01); C09K 11/06 (2013.01); C09K 2211/1044 (2013.01); C09K 2211/188 (2013.01); H10K 50/121 (2023.02); H10K 2101/90 (2023.02)] 20 Claims
 
1. An organic light-emitting device, comprising:
a first electrode;
a second electrode; and
an organic layer located between the first electrode and the second electrode, wherein the organic layer comprises an emission layer,
wherein the emission layer comprises a host, a sensitizer, and an emitter,
wherein the host, the sensitizer, and the emitter are different from each other, and
wherein the sensitizer is represented by Formula 1:
M1(L1)(L2)  Formula 1
wherein, in Formula 1,
M1 is Au, Ag, or Cu,
L1 is a ligand represented by Formula 2-1 or Formula 2-2, and
L2 is a ligand represented by Formula 3-3:

OG Complex Work Unit Chemistry
wherein, in Formulae 2-1, 2-2, and 3-3,
A21, A31, and A32 are each independently a monocyclic or polycyclic C5-C30 carbocyclic group or a monocyclic or polycyclic C1-C30 heterocyclic group,
X31 is a single bond, O, S, N(R36), C(R36)═C(R37), [C(R36)(R37)]n31, or [Si(R36)(R37)]n31, wherein n31 is 1 or 2,
R21 and R22 are each independently a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C7-C60 alkyl aryl group, a substituted or unsubstituted C7-C60 aryl alkyl group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted C2-C60 alkyl heteroaryl group, a substituted or unsubstituted C2-C60 heteroaryl alkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,
R33 and R34 are each independently a substituted or unsubstituted C1-C60 alkyl group,
R36 and R37 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, 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 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 C1-C60 alkylthio 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 alkyl aryl group, a substituted or unsubstituted C7-C60 aryl alkyl 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 C2-C60 alkyl heteroaryl group, a substituted or unsubstituted C2-C60 heteroaryl alkyl group, a substituted or unsubstituted C1-C60 heteroaryloxy group, a substituted or unsubstituted C1-C60 heteroarylthio 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), —Ge(Q1)(Q2)(Q3), —C(Q1)(Q2)(Q3), —B(Q1)(Q2), —N(Q1)(Q2), —P(Q1)(Q2), —C(═O)(Q1), —S(═O)(Q1), —S(═O)2(Q1), —P(═O)(Q1)(Q2), or —P(═S)(Q1)(Q2), and R36 and R37 are optionally linked to each other to form a substituted or unsubstituted C5-C30 carbocyclic group or a substituted or unsubstituted C1-C30 heterocyclic group, and
b23, b33, and b34 are each independently 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10,
a sum of b33 and b34 is 3 or greater,
wherein Q1 to Q3 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, 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 C1-C66 alkylthio 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 alkyl aryl group, a C7-C60 aryl alkyl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, a C2-C60 alkyl heteroaryl group, a C2-C60 heteroaryl alkyl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio 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, a cyano group, a C1-C20 alkyl group, and a C6-C30 aryl group, a C6-C60 aryl group, or a combination thereof, and
* indicates a binding site to M1 in Formula 1.