Organic light-emitting device

Patent metadata

Field	Value
Publication number	US-12490646-B2
Application number	US-202217677381-A
Country	US
Kind code	B2
Filing date	Feb 22, 2022
Priority date	Sep 17, 2021
Publication date	Dec 2, 2025
Grant date	Dec 2, 2025

Abstract

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:

M 1 (L 1 )(L 2 )  Formula 1

wherein, in Formula 1, M 1 is Au, Ag, or Cu, L 1 is a ligand represented by Formula 2-1 or Formula 2-2, and L 2 is a ligand represented by one of Formulae 3-1, 3-2, or 3-3:

wherein A 21 , A 31 , A 32 , X 31 , R 21 to R 24 , R 31 to R 35 , b23, and b33 are as defined herein, and * indicates a binding site to M 1 in Formula 1.

First claim

What is claimed is:

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:
M 1 (L 1 )(L 2 )  Formula 1

wherein, in Formula 1, M 1 is Au, Ag, or Cu, L 1 is a ligand represented by Formula 2-1 or Formula 2-2, and L 2 is a ligand represented by Formula 3-3:

wherein, in Formulae 2-1, 2-2, and 3-3,
A 21 , A 31 , and A 32 are each independently a monocyclic or polycyclic C 5 -C 30 carbocyclic group or a monocyclic or polycyclic C 1 -C 30 heterocyclic group,
X 31 is a single bond, O, S, N(R 36 ), C(R 36 )═C(R 37 ), [C(R 36 )(R 37 )] n31 , or [Si(R 36 )(R 37 )] n31 , wherein n31 is 1 or 2,
R 21 and R 22 are each independently a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 7 -C 60 alkyl aryl group, a substituted or unsubstituted C 7 -C 60 aryl alkyl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted C 2 -C 60 alkyl heteroaryl group, a substituted or unsubstituted C 2 -C 60 heteroaryl alkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,
R 33 and R 34 are each independently a substituted or unsubstituted C 1 -C 60 alkyl group,
R 36 and R 37 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF 5 , 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 C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 1 -C 60 alkylthio group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 7 -C 60 alkyl aryl group, a substituted or unsubstituted C 7 -C 60 aryl alkyl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted C 2 -C 60 alkyl heteroaryl group, a substituted or unsubstituted C 2 -C 60 heteroaryl alkyl group, a substituted or unsubstituted C 1 -C 60 heteroaryloxy group, a substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 1 )(Q 2 )(Q 3 ), —Ge(Q 1 )(Q 2 )(Q 3 ), —C(Q 1 )(Q 2 )(Q 3 ), —B(Q 1 )(Q 2 ), —N(Q 1 )(Q 2 ), —P(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O)(Q 1 ), —S(═O) 2 (Q 1 ), —P(═O)(Q 1 )(Q 2 ), or —P(═S)(Q 1 )(Q 2 ), and R 36 and R 37 are optionally linked to each other to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 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 Q 1 to Q 3 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF 5 , 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 C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 1 -C 66 alkylthio group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 7 -C 60 alkyl aryl group, a C 7 -C 60 aryl alkyl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a C 2 -C 60 alkyl heteroaryl group, a C 2 -C 60 heteroaryl alkyl group, a C 1 -C 60 heteroaryloxy group, a C 1 -C 60 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 C 1 -C 20 alkyl group, and a C 6 -C 30 aryl group, a C 6 -C 60 aryl group, or a combination thereof, and
* indicates a binding site to M 1 in Formula 1.

2 . The organic light-emitting device of claim 1 , wherein A 21 , A 31 , and A 32 are each independently a phenyl group, a naphthalene group, a phenanthrene group, a furan group, a thiophene group, a pyrrole group, a cyclopentene group, a silole group, a germole group, a benzofuran group, a benzothiophene group, an indole group, an indene group, a benzosilole group, a benzogermole group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a pyridine group, a pyrimidine group, a pyridazine group, or a pyrazine group.

3 . The organic light-emitting device of claim 1 , wherein
A 21 is a phenyl group, a naphthalene group, a pyridine group, a pyrimidine group, a pyridazine group, or a pyrazine group, and A 31 and A 32 are each independently a phenyl group, a naphthalene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a pyridine group, a pyrimidine group, a pyridazine group, or a pyrazine group.

4 . The organic light-emitting device of claim 1 , wherein
L 1 is a ligand represented by Formula 2-11 or Formula 2-12, and L 2 is a ligand represented by one of Formulae 3-13 to 3-17:

wherein, in Formulae 2-11, 2-12, and 3-13 to 3-17,
X 31 , R 23 , R 24 , R 34 , and R 35 are as defined in claim 1 , and
R 21a to R 21e , R 22a to R 22e , and R 23a to R 23d are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF 5 , —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a sulfonic acid group or a salt thereof, a C 1 -C 20 alkyl group, a deuterated C 2 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a C 1 -C 20 alkylthio group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a (C 1 -C 20 alkyl)cyclopentyl group, a (C 1 -C 20 alkyl)cyclohexyl group, a (C 1 -C 20 alkyl)cycloheptyl group, a (C 1 -C 20 alkyl)cyclooctyl group, a (C 1 -C 20

Assignees

• Samsung Electronics Co Ltd
• Ewha University—Industry Collaboration Found

Inventors

• Jung Yongsik
• You Youngmin
• Heo Seunga
• Kim Joonghyuk
• Choi Hyeonho
• Kim Inkoo
• Bae Hyejin

Classifications

• C09K2211/188

  of other metals not provided for in one of the previous groups · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C07F1/00

  Compounds containing elements of Groups 1 or 11 of the Periodic Table · CPC title

• H10K50/121

  for assisting energy transfer, e.g. sensitization · CPC title