Organometallic compound and organic light-emitting device including the same

Patent metadata

Field	Value
Publication number	US-11075345-B2
Application number	US-201715421715-A
Country	US
Kind code	B2
Filing date	Feb 1, 2017
Priority date	Apr 8, 2016
Publication date	Jul 27, 2021
Grant date	Jul 27, 2021

Abstract

An organometallic compound represented by one of Formulae 1A and 1B:

wherein, in Formulae 1A and 1B, A 11 , b20, L 11 , M, m, n, and R 15 to R 20 are the same as described in the specification.

First claim

What is claimed is:

1. An organometallic compound represented by one of Formulae 1A and 1B:

wherein, in Formulae 1A and 1B,
M is selected from M is selected from iridium (Ir), platinum (Pt), osmium (Os), ruthenium (Ru), rhodium (Rh), palladium (Pd), copper (Cu), silver (Ag), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), and thulium (Tm),
A 11 is selected from a C 5 -C 20 carbocyclic group,
R 15 and R 18 to R 20 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano 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 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 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, —O(Q 1 ), —S(Q 1 ), and —Si(Q 1 )(Q 2 )(Q 3 ),
wherein Q 1 to Q 3 are each independently selected from a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,
R 16 and R 17 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano 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 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 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, —O(Q 1 ), —S(Q 1 ), and —Si(Q 1 )(Q 2 )(Q 3 ),
wherein Q 1 to Q 3 are each independently selected from a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, R 16 and R 17 are optionally bound via Y 11 to form a ring,
Y 11 is a substituted or unsubstituted C 1 -C 5 alkylene group,
b20 is selected from 1, 2, 3, 4, 5, and 6,
n is selected from 1, 2, and 3,
L 11 is selected from a monodentate ligand and a bidentate ligand, and
m is selected from 0, 1, 2, 3, and 4.

2. The organometallic compound of claim 1 , wherein M is selected from Ir, Pt, and Os.

3. The organometallic compound of claim 1 , wherein M is Ir.

4. The organometallic compound of claim 1 , wherein A 11 is selected from a benzene group, a naphthalene group, a phenanthrene group, an anthracene group, a triphenylene group, a pyrene group, and a chrysene group.

5. The organometallic compound of claim 1 , wherein A 11 is selected from a benzene group and a naphthalene group.

6. The organometallic compound of claim 1 , wherein A 11 is a benzene group.

7. The organometallic compound of claim 1 , wherein
R 15 and R 18 to R 20 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a substituted or unsubstituted C 1 -C 60 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 6 -C 60 aryl 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, —O(Q 1 ), —S(Q 1 ), and —Si(Q 1 )(Q 2 )(Q 3 ),
wherein Q 1 to Q 3 are each independently selected from a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 6 -C 60 aryl group, and a substituted or unsubstituted C 1 -C 60 heteroaryl group,
R 16 and R 17 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 6 -C 60 aryl 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, —O(Q 1 ), —S(Q 1 ), and —Si(Q 1 )(Q 2 )(Q 3 ),
wherein Q 1 to Q 3 are each independently selected from a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 6 -C 60 aryl group, and a substituted or unsubstituted C 1 -C 60 heteroaryl group, and
R 16 and R 17 are optionally bound via Y 11 to form a ring.

8. The organometallic compound of claim 1 , wherein
R 15 and R 18 to R 20 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a C 1 -C 20 alkyl group, a C 3 -C 10 cycloalkyl group, and a C 1 -C 10 heterocycloalkyl group;
a C 1 -C 20 alkyl group, a C 3 -C 10 cycloalkyl group, and a C 1 -C 10 heterocycloalkyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, and —I;
a phenyl group, a naphthyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group;
a phenyl group, a naphthyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, and —Si(Q 11 )(Q 12 )(Q 13 );
a phenyl group, a naphthyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group, each substituted with at least one selected from a C 1 -C 20 alkyl group, a phenyl group, and a naphthyl group that are each substituted with at least one selected from deuterium, —F, —Cl, —Br, and —I; and
—O(Q 1 ), —S(Q 1 ) and —Si(Q 1 )(Q 2 )(Q 3 ),
wherein Q 1 to Q 3 and Q 11 to Q 13 are each independently selected from a C 1 -C 20 alkyl group, a phenyl group, and a naphthyl group; and
a C 1 -C 20 alkyl group, a phenyl group, and a naphthyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, and —I,
R 16 and R 17 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, and a C 1 -C 10 heterocycloalkyl group;
a C 1 -

Assignees

• Samsung Electronics Co Ltd
• Samsung Sdi Co Ltd

Inventors

• Ishibe Satoko
• Bae Hyejin
• Kim Wook
• Noh Changho
• Park Sangho
• Rai Virendra Kumar
• Chae Miyoung
• Kravchuk Dmitry

Classifications

• C07F15/00 Primary

  Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table · CPC title

• C09K2211/185

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

• C07F15/0033 Primary

  Iridium compounds · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title