Organometallic compound, organic light-emitting device including the same, and electronic apparatus including the organic light-emitting device

Patent metadata

Field	Value
Publication number	US-12588404-B2
Application number	US-202217841088-A
Country	US
Kind code	B2
Filing date	Jun 15, 2022
Priority date	Jul 22, 2021
Publication date	Mar 24, 2026
Grant date	Mar 24, 2026

Abstract

An organometallic compound, represented by Formula 1: M1(Ln1)n1(Ln2)n2  Formula 1 wherein, in Formula 1, M1 is a transition metal, Ln1 is a ligand represented by Formula 1A, Ln2 is a ligand represented by Formula 1B, n1 is 1 or 2, and n2 is 1 or 2: wherein the substituents of Formulae 1A and 1B are as provided herein in the detailed description.

First claim

What is claimed is:

1 . An organometallic compound, represented by Formula 1:
M 1 (Ln 1 ) n1 (Ln 2 ) n2   Formula 1
wherein, in Formula 1,
M 1 is a transition metal,
Ln 1 is a ligand represented by Formula 1A,
Ln 2 is a ligand represented by Formula 1B,
n1 is 1 or 2,
n2 is 1 or 2,

wherein, in Formulae 1A, 1B, 3B, and 40,
CY 1 and CY 2 are each a C 5 -C 30 carbocyclic group or a C 1 -C 30 heterocyclic group,
CY 3 is represented by Formula 3B,
CY 4 is a group represented by Formula 40,
X 1 is C or N, and X 2 is C or N,
X 3 is N, and X 4 is C or N,
Y 1 is —O—, —S—, —Se—, —C(R 3 )(R 4 )—, —N(R 3 )—, or —B(R 3 )—,
Y 41 and Y 42 are each independently a single bond, —O—, —S—, —Se—, —C(R 5 )(R 6 )—, —N(R 5 )—, or —B(R 5 )—,
Y 41 and Y 42 are not both a single bond at the same time,
X 31 is C(R 31 ) or N, X 32 is C(R 32 ) or N, X 33 is C(R 33 ) or N, X 34 is C(R 34 ) or N, and X 35 is C(R 35 )R 36 ) or N(R 35 ),
R 10 and R 20 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF 5 , 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 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 2 -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, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,
R 1 to R 6 , R 30 , R 31 to R 36 , and R 40 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF 5 , 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 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 2 -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 ), —N(Q 4 )(Q 5 ), —B(Q 6 )(Q 7 ), —P(Q 8 )(Q 9 ), or —P(═O)(Q 8 )(Q 9 ),
when Y 1 is —O—, then at least one R 30 is a group represented by Formulae 10-13 to 10-47, 10-49 to 10-154, 10-204, or 10-205:

two or more of a plurality of R 10 (s) are optionally linked together to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group,
two or more of a plurality of R 20 (s) are optionally linked together to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group,
two or more of a plurality of R 30 (s) are optionally linked together to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group,
two or more of a plurality of R 40 (s) are optionally linked together to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group,
neighboring two or more of R 1 to R 6 , R 10 , R 20 , R 30 , and R 40 are optionally linked together to form a substituted or unsubstituted C 5 -C 30 carbocyclic group or a substituted or unsubstituted C 1 -C 30 heterocyclic group,
b10, b20, and b40 are each independently 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10,
in Formulae 1A, and 1B, * and *′ each indicate a binding site to M 1 ,
in Formula 3B, * indicates a binding site to M 1 and,

Assignees

• Samsung Electronics Co Ltd
• Samsung Display Co Ltd

Inventors

• Kwon Ohyun
• Rai Virendra Kumar
• Park Bumwoo
• Kim Sangdong
• Kim Hyungjun
• Choi Byoungki

Classifications

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title

• C09K2211/1048

  with oxygen · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C07F15/0033 Primary

  Iridium compounds · CPC title