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

Patent metadata

Field	Value
Publication number	US-11716897-B2
Application number	US-201816051231-A
Country	US
Kind code	B2
Filing date	Jul 31, 2018
Priority date	Jan 17, 2018
Publication date	Aug 1, 2023
Grant date	Aug 1, 2023

Abstract

Provided are an organometallic compound represented by Formula 1, an organic light-emitting device including the organometallic compound, and an organic light-emitting apparatus including the organic light-emitting device. The organic light-emitting device includes: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode, the organic layer including an emission layer and at least one of the organometallic compound represented by Formula 1.

First claim

What is claimed is:

1. An organometallic compound represented by Formula 1:

wherein M in Formula 1 is a transition metal,
in Formula 1, Li is a ligand represented by Formula 2a, and n1 is 1 or 2, wherein, when n1 is two or more, two or more Li(s) are identical to or different from each other,
in Formula 1, L 2 is a ligand represented by Formula 5-1 or 5-2, wherein, in Formulae 5-1 and 5-2, Y 51 is O, Y 52 is O, and T 51 is *—C(R 51a )═C(R 51b )—C(R 51c )═*′, and n2 is 1 or 2, wherein, when n2 is two or more, two or more L 2 (s) are identical to or different from each other,
the sum of n1 and n2 in Formula 1 is 2 or 3,
wherein, in Formula 2a,
A 11 and A 12 form a condensed ring sharing two carbon atoms,
A 11 is selected from a pyrrole group, a benzimidazole group, an indole group, an isoindole group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a pyridine group, a pyrazine group, a pyrimidine group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, and a triazine group,
A 12 is selected from a benzene group, a naphthalene group, an indene group, an azulene group, a pyrrole group, an imidazole group, a benzimidazole group, an indole group, an isoindole group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, and a triazine group,
A 2 in Formula 2a is a condensed ring in which at least two groups selected from a 5-membered carbocyclic group, a 5-membered heterocyclic group, a 7-membered carbocyclic group, and a 7-membered heterocyclic group are condensed to each other,
R 2 , R 11 and R 12 in Formula 2a are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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 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 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 monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —P(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), and —P(═O)(Q 1 )(Q 2 ),
R 51a to R 53c in Formulae 5-1 and 5-2 are defined the same as R 2 in Formula 2a,
a2, all and 12 in Formula 2a are each independently an integer from 1 to 6, wherein, when all is two or more, two or more R 11 (s) are identical to or different from each other, when a2 is two or more, two or more R 12 (5) are identical to or different from each other, and when a2 is two or more, two or more R 2 (s) are identical to or different from each other,
* and *′ in Formula 2a each indicate a binding site to M in Formula 1, and *″ in Formulae 2-1 and 2-2 indicates a binding site to A 1 ,
at least one substituent of the substituted C 1 -C 60 alkyl group, the substituted C 2 -C 60 alkenyl group, the substituted C 2 -C 60 alkynyl group, the substituted C 1 -C 60 alkoxy group, the substituted C 3 -C 10 cycloalkyl group, the substituted C 1 -C 10 heterocycloalkyl group, the substituted C 3 -C 10 cycloalkenyl group, the substituted C 1 -C 10 heterocycloalkenyl group, the substituted C 6 -C 60 aryl group, the substituted C 6 -C 60 aryloxy group, the substituted C 6 -C 60 arylthio group, the substituted C 1 -C 60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is selected from:
deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group;
a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a C 1 -C 60 alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono 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 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 11 )(Q 12 )(Q 13 ), —N(Q 11 )(Q 12 ), —B(Q 11 )(Q 12 ), —P(Q 11 )(Q 12 ), —C(═O)(Q 11 ), —S(═O) 2 (Q 11 ), and —P(═O)(Q 11 )(Q 12 );
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 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic 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 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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 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 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q 21 )(Q 22 )(Q 23 ), —N(Q 21 )(Q 22 ), —B(Q 21 )(Q 22 ), —P(Q 21 )(Q 22 ), —C(═O)(Q 21 ), —S(═O) 2 (Q 21 ), and —P(═O)(Q 21 )(Q 22 ); and
—Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 31 )(Q 32 ), —B(Q 31 )(Q 32 ), —P(Q 31 )(Q 32 ), —C(═O)(Q 31 ), —S(═O) 2 (Q 31 ), and —P(═O)(Q 31 )(Q 32 ), and
Q 1 to Q 3 , Q 11 to Q 13 , Q 21 to Q 23 , Q 31 to Q 33 , and Q 41 to Q 42 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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 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 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalen

Assignees

• Samsung Display Co Ltd

Inventors

• Yoo Byeongwook
• Kang Sunwoo
• Kim Myeongsuk
• Kim Hyoyeon
• Ye Jimyoung
• Yoon Jihwan

Classifications

• C07F15/0033 Primary

  Iridium compounds · CPC title

• H10K85/342 Primary

  comprising iridium · CPC title

• H10K50/12

  comprising dopants · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• H10K50/15

  Hole transporting layers · CPC title