Organometallic compound and organic light-emitting device including the same

Patent metadata

Field	Value
Publication number	US-10290818-B2
Application number	US-201615064112-A
Country	US
Kind code	B2
Filing date	Mar 8, 2016
Priority date	Oct 14, 2015
Publication date	May 14, 2019
Grant date	May 14, 2019

Abstract

An organometallic compound represented by Formula 1:

wherein, in Formula 1, L 11 , M, R 11 to R 17 , m, 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 Formula 1,
M is selected from a Period 4 transition metal, a Period 5 transition metal, and a Period 6 transition metal, EU, Tb, and Tm;
R 11 to R 17 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 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, and —Si(Q 1 )(Q 2 )(Q 3 ); two adjacent groups selected from R 11 to R 16 are optionally linked to each other to form a saturated or unsaturated ring;
R 17 is selected from 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;
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 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 6 -C 60 aryl group, and a substituted or unsubstituted C 1 -C 60 heteroaryl group;
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, Os, Ru, Rh, Pd, Cu, Ag, Au, Ti, Zr, Hf, Eu, Tb, and Tm.

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

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

5. The organometallic compound of claim 1 , wherein
R 11 to R 17 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, 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 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, and —Si(Q 1 )(Q 2 )(Q 3 );
two adjacent groups selected from of R 11 to R 16 are optionally linked to each other to form a saturated or unsaturated ring;
R 17 is selected from 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; and
Q 1 to Q 3 are each independently selected from a substituted or unsubstituted C 1 -C 60 alkyl group and a substituted or unsubstituted C 6 -C 60 aryl group.

6. The organometallic compound of claim 1 , wherein
R 11 to R 17 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy 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 1 -C 20 alkoxy 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, an isoquinolinyl group, a dibenzofuranyl group, and a dibenzothiophenyl 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, an isoquinolinyl group, a dibenzofuranyl group, and a dibenzothiophenyl 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 ); and
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, an isoquinolinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one selected from 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;
two adjacent groups selected from R 11 to R 16 are optionally linked to each other to form a saturated or unsaturated ring;
R 17 is selected from 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, an isoquinolinyl group, a dibenzofuranyl group, and a dibenzothiophenyl 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, an isoquinolinyl group, a dibenzofuranyl group, and a dibenzothiophenyl 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, and a naphthyl group; and
a phenyl group, a naphthyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrdinyl group, a pyrazinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one selected from 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; and
Q 11 to Q 13 are each independently selected from a methyl group, an ethyl group, and a phenyl group.

7. The organometallic compound of claim 1 , wherein
R 11 to R 17 are each independently selected from hydrogen, deuterium, —F, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, an n-pentyl group, a methoxy group, an ethoxy group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group;
a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, an n-pentyl group, a m

Assignees

• Samsung Electronics Co Ltd
• Samsung Sdi Co Ltd

Inventors

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

Classifications

• H01L51/0085 Primary

  Electricity · mapped topic

• H01L51/5016

  Electricity · mapped topic

• C09K2211/185

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

• C09K11/06

  containing organic luminescent materials · CPC title

• C07F15/0033 Primary

  Iridium compounds · CPC title