Organometallic compound and organic light-emitting device including the same

Patent metadata

Field	Value
Publication number	US-10672995-B2
Application number	US-201514801080-A
Country	US
Kind code	B2
Filing date	Jul 16, 2015
Priority date	Jul 24, 2014
Publication date	Jun 2, 2020
Grant date	Jun 2, 2020

Abstract

An organometallic compound represented by Formula 1:

Ir(L 1 ) n (L 2 ) (3-n)   Formula 1
wherein in Formula 1, L 1 , L 2 , and n are the same as described in the specification.

First claim

What is claimed is:

1. An organometallic compound represented by Formula 1:

wherein in Formulae 1 to 3,
L 1 is a first ligand represented by Formula 2;
L 2 is a second ligand represented by Formula 3, wherein L 2 includes at least one cyano group as a substituent;
n is selected from 2 and 3;
A 11 is selected from a C 6 -C 60 cyclic group and a C 1 -C 60 heterocyclic group selected from an imidazole, a pyrazole, an isothiazole, an isoxazole, a pyrazine, a pyridazine, a quinoline, an isoquinoline, a benzoquinoline, a quinoxaline, a quinazoline, a benzoimidazole, a benzoxazole, an isobenzoxazole, a triazole, a tetrazole, an oxadiazole, a triazine, a pyridoindole, a pyridofuran, and a pyridothiophene, each comprising Y 11 as a cyclic ring member;
A 21 , and A 22 are each independently selected from a naphthalene, an anthracene, a phenanthrene, a pyrrole, an imidazole, a pyrazole, a thiazole, an isothiazole, an oxazole, an isoxazole, a pyridine, a pyrazine, a pyrimidine, a pyridazine, a quinoline, an isoquinoline, a benzoquinoline, a quinoxaline, a quinazoline, a benzoimidazole, a benzoxazole, an isobenzoxazole, a triazole, a tetrazole, an oxadiazole, a triazine, a pyridoindole, a pyridofuran, and a pyridothiophene;
Y 11 , Y 12 , Y 21 , and Y 22 are each independently selected from C and N;
X 13 is N or CR 13 ;
X 14 is N or CR 14 ;
X 15 is N or CR 15 ;
X 16 is N or CR 16 ;
X 17 is N or CR 17 ;
X 18 is N or CR 18 ;
X 19 is N or CR 19 ;
X 23 is N or CR 23 ; and
X 24 is N or CR 24 ;
provided that when A 11 is an imidazole, X 13 is CR 13 , X 14 is CR 14 , X 15 is CR 15 , X 16 is CR 16 , X 17 is CR 17 , X 18 is CR 18 , and X 19 is CR 19 , then n in Formula 1 is 2, and the second ligand is represented by Formula 3A:

wherein in Formula 3A,
Y 21 and Y 22 are each independently selected from C and N;
X 21 is N or CR 21 , X 23 is N or CR 23 , and X 25 is N or CR 25 ;
provided that when Y 22 is C, then X 25 is N;
provided that when X 25 is C, then Y 22 is N;
R 21 to R 27 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a cyano group, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 6 -C 60 aryl group, and a substituted or unsubstituted C 1 -C 60 heteroaryl group, wherein at least one of R 21 to R 27 is a cyano group;
* and *′ are each independently a binding site to a neighboring atom;
at least one substituent of the substituted C 1 -C 60 alkyl group, substituted C 1 -C 60 alkoxy group, substituted C 6 -C 60 aryl group, and substituted C 1 -C 60 heteroaryl group is selected from
a deuterium, —F, —Cl, —Br, —I, a C 1 -C 60 alkyl group, and a C 1 -C 60 alkoxy group;
a C 1 -C 60 alkyl group and a C 1 -C 60 alkoxy group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, and —Si(Q 11 )(Q 12 )(Q 13 );
a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, and a C 1 -C 60 heteroaryl group;
a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, and a C 1 -C 60 heteroaryl group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy 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, and —Si(Q 21 )(Q 22 )(Q 23 ); and
—Si(Q 31 )(Q 32 )(Q 33 ),
wherein Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 are each independently selected from a C 1 -C 60 alkyl group and a C 6 -C 60 aryl group;
wherein in Formula 2 and 3,
R 11 to R 19 , R 23 , R 24 , R 28 , and R 29 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a cyano group, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 6 -C 60 aryl group, and a substituted or unsubstituted C 1 -C 60 heteroaryl group;
a11, a28, and a29 are each independently selected from 1, 2, 3, 4, 5, and 6;
R 12 and R 13 are optionally linked to each other via a divalent linking group selected from a single bond, *—O—*′, *—S—*′, *—N(Z 11 )—*′, and *—[C(Z 11 )(Z 12 )] b11 —*′; wherein
Z 11 and Z 12 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a substituted or unsubstituted C 1 -C 60 alkyl group, and a substituted or unsubstituted C 6 -C 60 aryl group;
b11 is selected from 1, 2, 3, and 4;
* and *′ are each independently a binding site to a neighboring atom;
a11 is selected from 1, 2, and 3;
* and *′ indicates a binding site to a neighboring atom;
at least one substituent of the substituted C 1 -C 60 alkyl group, substituted C 1 -C 60 alkoxy group, substituted C 6 -C 60 aryl group, and substituted C 1 -C 60 heteroaryl group is selected from
a deuterium, —F, —Cl, —Br, —I, a C 1 -C 60 alkyl group, and a C 1 -C 60 alkoxy group;
a C 1 -C 60 alkyl group and a C 1 -C 60 alkoxy group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, and —Si(Q 11 )(Q 12 )(Q 13 );
a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, and a C 1 -C 60 heteroaryl group;
a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, and a C 1 -C 60 heteroaryl group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy 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, and —Si(Q 21 )(Q 22 )(Q 23 ); and
—Si(Q 31 )(Q 32 )(Q 33 ),
wherein Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 are each independently selected from a C 1 -C 60 alkyl group and C 6 -C 60 aryl group.

2. The organometallic compound of claim 1 , wherein
L 1 comprises at least one cyano group as a substituent.

3. The organometallic compound of claim 1 , wherein
A 11 is selected from a benzene, a naphthalene, an anthracene, and a phenanthrene.

4. The organometallic compound of claim 1 , wherein A 11 is each independently selected from a benzene and a naphthalene.

5. The organometallic compound of claim 1 , wherein A 21 and A 22 are each independently selected from a naphthalene, a pyrrole, an imidazole, a pyrazole, a pyridine, a pyrazine, a pyrimidine, a pyridazine, a quinoline, an isoquinoline, a quinoxaline, a quinazoline, a triazole, and a tetrazole.

6. The organometallic compound of claim 1 , wherein
Y 11 and Y 12 are different from each other, and Y 21 and Y 22 are different from each other.

7. The organometallic compound of claim 1 , wherein
R 11 to R 19 , R 23 , R 24 , R 28 , and R 29 are each independently a hydrogen, a deuterium, —F, —Cl, —Br, —I, a cyano group, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a C 6 -C 60 aryl group, and a C 1 -C 60 heteroaryl group;
a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a C 6 -C 60 aryl group, and a C 1 -C 60 heteroaryl group, each subst

Assignees

• Samsung Electronics Co Ltd
• Samsung Sdi Co Ltd

Inventors

• Das Rupasree Ragini
• Lee Kangmun
• Noh Changho
• Bae Hyejin
• Rai Virendra Kumar
• Kravchuk Dmitry

Classifications

• C09K11/06

  containing organic luminescent materials · CPC title

• H01L51/0059

  Electricity · mapped topic

• C09K2211/1074

  containing more than three nitrogen atoms as heteroatoms · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• C09K2211/1059

  containing three nitrogen atoms as heteroatoms · CPC title