Organometallic compound, composition containing the organometallic compound, and organic light-emitting device including the organometallic compound or composition

Patent metadata

Field	Value
Publication number	US-10326086-B2
Application number	US-201615013404-A
Country	US
Kind code	B2
Filing date	Feb 2, 2016
Priority date	Feb 6, 2015
Publication date	Jun 18, 2019
Grant date	Jun 18, 2019

Abstract

An organometallic compound represented by Formula 1:

wherein, in Formula 1, groups an variables are the same as described in the specification.

First claim

What is claimed is:

1. An organometallic compound represented by Formula 1:

wherein, in Formula 1,
M 11 is a first-row transition metal, a second-row transition metal, or a third-row transition metal;
R 11 to R 18 are each independently a hydrogen, a deuterium, —F, —CI, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a carbonyl 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 30 alkyl group, a substituted or unsubstituted C 3 -C 30 branched alkyl group, a substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 2 -C 30 alkynyl group, a substituted or unsubstituted C 1 -C 30 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 30 aryl group, a substituted or unsubstituted C 6 -C 30 aryloxy group, a substituted or unsubstituted C 6 -C 30 arylthio group, a substituted or unsubstituted C 7 -C 30 arylalkyl group, a substituted or unsubstituted C 1 -C 30 heteroaryl group, a substituted or unsubstituted C 2 -C 30 heteroaryloxy group, a substituted or unsubstituted C 2 -C 30 heteroarylthio group, a substituted or unsubstituted C 3 -C 30 heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, or a substituted or unsubstituted C 1 -C 30 alkylsilyl group;
optionally, adjacent two of R 11 to R 15 are linked to form a substituted or unsubstituted saturated ring, or a substituted or unsubstituted unsaturated ring;
at least one of R 11 to R 15 is selected from the group consisting of a substituted or unsubstituted C 3 -C 30 branched alkyl 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 30 aryl group, a substituted or unsubstituted C 6 -C 30 aryloxy group, a substituted or unsubstituted C 6 -C 30 arylthio group, a substituted or unsubstituted C 7 -C 30 arylalkyl group, a substituted or unsubstituted C 1 -C 30 heteroaryl group, a substituted or unsubstituted C 2 -C 30 heteroaryloxy group, a substituted or unsubstituted C 2 -C 30 heteroarylthio group, a substituted or unsubstituted C 3 -C 30 heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and a substituted or unsubstituted C 1 -C 30 alkylsilyl group;
R 19 and R 20 are each independently a hydrogen, a deuterium, a C 1 -C 30 alkyl group, or a deuterium-substituted C 1 -C 30 alkyl group;
at least one of R 11 to R 20 is a deuterium-containing substituent;
n11 is 1, 2, or 3;
L 11 is a monodentate ligand or a bidentate ligand selected from the group consisting of an oxalate, an acetylacetonate, a picolinic acid, a 1,2-bis(diphenylphosphino)ethane, a 1,1-bis(diphenylphosphino)methane, a glycinate, an ethylenediamine, and ligands represented by Formulae 4-1 to 4-4:

wherein, in Formulae 4-1 to 4-4,
X 41 iS CR 41 or a nitrogen atom (N);
X 42 is CR 42 or N;
X 45 iS O, S, or N(R 45 );
Y 41 and Y 42 are each independently C or N;
Z 21 and Z 22 are each independently N, O, N(R 48 ), P(R 48 )(R 49 ), or As(R 48 )(R 49 );
Z 23 is CO or CH 2 ;
A 41 to A 43 are each independently a C 3 -C 10 cycloalkane, a C 1 -C 10 heterocycloalkane, a C 3 -C 10 cycloalkene, a C 1 -C 10 heterocycloalkene, a C 6 -C 10 arene, a C 1 -C 10 heteroarene, a non-aromatic condensed polycycle, or a non-aromatic condensed heteropolycycle, wherein a bond between A 41 and A 42 in Formula 4-1 is a carbon-carbon bond;
R 41 to R 49 are each independently a hydrogen, a deuterium, —F, —CI, —Br, —I, 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 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 7 -C 30 arylalkyl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted C 2 -C 30 heteroaryloxy group, a substituted or unsubstituted C 2 -C 30 heteroarylthio group, a substituted or unsubstituted C 3 -C 30 heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, or —Si(Q 41 )(Q 42 )(Q 43 );
optionally, adjacent two of R 41 to R 44 are linked to form a substituted or unsubstituted saturated ring, or a substituted or unsubstituted unsaturated ring;
optionally, R 46 and R 47 are linked to form a substituted or unsubstituted saturated ring or a substituted or unsubstituted unsaturated ring;
b43 and b44 are each independently an integer of 1 to 5;
Q 41 to Q 43 are each independently a hydrogen, a deuterium, —F, —CI, —Br, —I, 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, 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 7 -C 60 arylalkyl group, a C 1 -C 60 heteroaryl group, a C 2 -C 60 heteroaryloxy group, a C 2 -C 60 heteroarylthio group, a C 3 -C 60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group; and
* and *′ are each independently a binding site to M 11 in Formula 1; and
m11 is 0, 1, 2, 3, or 4.

2. The organometallic compound of claim 1 , wherein M 11 is Ir or Pt.

3. The organometallic compound of claim 1 , wherein R 11 to R 18 are each independently a hydrogen, a deuterium, —F, —Cl, —Br, —I, a substituted or unsubstituted C 1 -C 10 alkyl group, a substituted or unsubstituted C 3 -C 30 branched alkyl group, a substituted or unsubstituted

Assignees

• Samsung Electronics Co Ltd
• Samsung Sdi Co Ltd

Inventors

• Kim Wook
• Noh Changho
• Das Rupasree Ragini
• Park Youngseok
• Bae Hyejin
• Chae Miyoung
• Kravchuk Dmitry

Classifications

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• H01L51/0067

  Electricity · mapped topic

• H01L51/006

  Electricity · mapped topic

• H01L51/5016

  Electricity · mapped topic

• C09K2211/1088

  containing oxygen as the only heteroatom · CPC title