Organic light-emitting device, apparatus including the same, and organometallic compound

Patent metadata

Field	Value
Publication number	US-12289985-B2
Application number	US-201916446130-A
Country	US
Kind code	B2
Filing date	Jun 19, 2019
Priority date	Sep 21, 2018
Publication date	Apr 29, 2025
Grant date	Apr 29, 2025

Abstract

Provided are an organic light-emitting device, an apparatus including the organic light-emitting device, and an organometallic compound represented by Formula 1. The organic light-emitting device includes: a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode and including an emission layer, wherein: the organic layer includes the organometallic compound represented by 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 between the first electrode and the second electrode and comprising an emission layer, wherein:
the organic layer comprises an organometallic compound represented by Formula 1:

wherein, in Formulae 1, 1-1, 2-1, 2-26, 3-1, and 3-2,
M 1 is selected from a Period 1 transition metal, a Period 2 transition metal, and a Period 3 transition metal;
*1 to *4 each indicate a binding site to M 1 ;
L 1 is a ligand represented by Formula 1-1;
L 2 is selected from a monodentate ligand and a bidentate ligand;
n1 is 1,
n2 is selected from 0, 1, and 2;
A 11 to A 14 are each independently selected from a group represented by Formula 2-1, a group represented by Formula 2-26, a group represented by Formula 3-1, a group represented by Formula 3-2, a C 5 -C 60 carbocyclic group, and a C 1 -C 60 heterocyclic group;
at least one selected from A 11 to A 14 is selected from a group represented by Formula 2-1 and a group represented by Formula 2-26; and
at least one selected from A 11 to A 14 is selected from a group represented by Formula 3-1 and a group represented by Formula 3-2;
Y 11 to Y 14 are each independently selected from N and C;
T 11 to T 14 are each independently selected from a single bond, *—O—* ‘, and *—S—*’;
L 11 to L 14 are each independently selected from a single bond, *—O—*′, *—S—*′, *—C(R 17 )(R 18 )—*′, *—C(R 17 )═*′, *═C(R 17 )—*′, *—C(R 17 )═C(R 18 )—*′, *—C(═O)—*′, *—C(═S)—*′, *—C═C—*′, *—B(R 17 )—*′, *—N(R 17 )—*′, *—P(R 17 )—*′, *—Si(R 17 )(R 18 )—*′, *—P(R 17 )(R 18 )—*′, and *—Ge(R 17 )(R 18 )—**;
a11 to a14 are each independently selected from 0, 1, 2, and 3, and at least three selected from a11 to a14 are selected from 1, 2, and 3;
when a11 is 0, A 11 and A 12 are not linked to each other, when a12 is 0, A 12 and A 13 are not linked to each other, when a13 is 0, A 13 and A 14 are not linked to each other, and when a14 is 0, A 14 and A 11 are not linked to each other,
R 11 to R 14 , R 17 , and R 18 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 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 ), —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 ), and —P(═S)(Q 1 )(Q 2 );
R 17 and R 11 , R 17 and R 12 , R 17 and R 13 , and/or R 17 and R 14 are optionally linked to each other to form a substituted or unsubstituted C 5 -C 60 carbocyclic group or a substituted or unsubstituted C 1 -C 60 heterocyclic group,
R 17 and R 18 are optionally linked to each other to form a substituted or unsubstituted C 5 -C 60 carbocyclic group or a substituted or unsubstituted C 1 -C 60 heterocyclic group,
b11 to b14 are each independently selected from 1, 2, 3, 4, 5, 6, 7, and 8;
X 21 is selected from O, S, N(R 24 ), and C(R 24 )(R 25 );
X 22 to X 25 are each independently selected from N and C,
X 26a is N, N—*, or C(R 26a ), X 26b is N, N—*, or C(R 26b ), X 26c is N, N—*, or C(R 26c ), X 26d is N, N—*, or C(R 26d ), X 26e is N, N—*, or C(R 26e ), X 26f is N, N—*, or C(R 26f ), X 26g is N, N—*, or C(R 26g ), X 26h is N, N—*, or C(R 26h ),
A 21 and A 22 are each independently selected from a C 5 -C 60 carbocyclic group and a C 1 -C 60 heterocyclic group;
X 31 is N, N—*, or C(R 31 ), X 32 is N, N—*, or C(R 32 ), X 33 is N, N—*, or C(R 33 ), X 34 is N, N—*, or C(R 34 ), X 35 is N, N—*, or C(R 35 ), X 36 is N, N—*, or C(R 36 ), X 37 is N, N—*, or C(R 37 ), and X 38 is N, N—*, or C(R 38 ),
two or more selected from X 31 to X 34 are each independently N or N—*,
one or more selected from X 35 to X 38 each independently N or N—*,
A 31 is selected from a C 5 -C 60 carbocyclic group and a C 1 -C 60 heterocyclic group;
A 32 is a C 1 -C 60 heterocyclic group containing at least one N,
R 21 to R 25 , R 26a to R 26h , and R 31 to R 39 are each independently selected from a binding site, 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 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 ), —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 ), and —P(═S)(Q 1 )(Q 2 );
one, two, or three selected from R 21 to R 25 are binding sites,
one, two, or three selected from R 24 , R 25 and R 26a to R 26h in Formula 2-26 are binding sites,
one, two, or three selected from R 31 to R 34 and R 39 are binding sites,
one, two, or three selected from R 35 to R 39 are binding sites,
Q 1 to Q 3 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 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a C 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group;
provided that none of A 11 to

Assignees

• Samsung Display Co Ltd

Inventors

• Kim Myeongsuk
• Ye Jimyoung
• Yoo Byeongwook
• Cho Illhun
• Kang Sunwoo
• Kim Sunjae
• Jeong Jaeho

Classifications

• H10K59/90

  Assemblies of multiple devices comprising at least one organic light-emitting element · CPC title

• H10K50/82

  Cathodes · CPC title

• H10K50/81

  Anodes · CPC title

• C07F15/0086 Primary

  Platinum compounds · CPC title

• H10K85/346 Primary

  comprising platinum · CPC title