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

Patent metadata

Field	Value
Publication number	US-10164198-B2
Application number	US-201514810863-A
Country	US
Kind code	B2
Filing date	Jul 28, 2015
Priority date	Feb 5, 2015
Publication date	Dec 25, 2018
Grant date	Dec 25, 2018

Abstract

An organometallic compound represented by Formula 1:

wherein in Formula 1, R 11 to R 20 , L 11 , m 11 , and n 11 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,
R 11 , R 12 , and R 14 to R 18 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxy 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 10 alkyl group, a substituted or unsubstituted C 2 -C 10 alkenyl group, a substituted or unsubstituted C 2 -C 10 alkynyl group, and a substituted or unsubstituted C 1 -C 10 alkoxy group;
R 13 is selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxy 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 10 linear alkyl group, a substituted or unsubstituted C 2 -C 10 alkenyl group, a substituted or unsubstituted C 2 -C 10 alkynyl group, and a substituted or unsubstituted C 1 -C 10 alkoxy group;
R 19 and R 20 are each independently selected from a hydrogen, a deuterium, a C 1 -C 10 alkyl group, and a C 1 -C 10 alkyl group substituted with a deuterium;
R 11 and R 12 , R 12 and R 13 , R 13 and R 14 , or R 14 and R 15 are optionally linked to each other to form a condensed ring;
at least one selected from R 11 to R 20 is a C 1 -C 10 alkyl group substituted with a deuterium, provided that when R 13 is selected, R 13 is a C 1 -C 10 linear alkyl group substituted with a deuterium;
n11 is selected from 1, 2, and 3;
L 11 is selected from a monodentate ligand and a bidentate ligand; and
m11 is selected from 0, 1, 2, 3, and 4.

2. The organometallic compound of claim 1 , wherein
R 11 , R 12 , and R 14 to R 18 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxy 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, and a substituted or unsubstituted C 1 -C 10 alkyl group.

3. The organometallic compound of claim 1 , wherein
R 11 , R 12 , and R 14 to R 18 are each independently selected from
a hydrogen, a deuterium, —F, —Cl, —Br, —I, a cyano 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, an iso-pentyl group, a 1-methylbutyl group, a 2-methylbutyl group, a neo-pentyl group, a 1,2-dimethylpropyl group, and a tert-pentyl group; and
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, an iso-pentyl group, a 1-methylbutyl group, a 2-methylbutyl group, a neo-pentyl group, a 1,2-dimethylpropyl group, and a tert-pentyl group, each substituted with a deuterium.

4. The organometallic compound of claim 1 , wherein
at least one of R 11 is R 15 are independently selected from
a hydrogen, a deuterium, —F, —Cl, —Br, —I, a cyano 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, and a tert-butyl group; and
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, and a tert-butyl group, each substituted with a deuterium.

5. The organometallic compound of claim 1 , wherein
R 13 is selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxy 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, and a substituted or unsubstituted C 1 -C 10 linear alkyl group.

6. The organometallic compound of claim 1 , wherein
R 13 is selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a cyano group, a methyl group, an ethyl group, an n-propyl group, an n-butyl group, and an n-pentyl group; and
a methyl group, an ethyl group, an n-propyl group, an n-butyl group, and an n-pentyl group, each substituted with a deuterium.

7. The organometallic compound of claim 1 , wherein
R 19 is a deuterium, and R 20 is a hydrogen;
R 19 is a hydrogen, and R 20 is a deuterium; or
R 19 and R 20 are both a deuterium.

8. The organometallic compound of claim 1 , wherein at least one of R 11 and R 15 is a C 1 -C 10 alkyl group substituted with a deuterium.

9. The organometallic compound of claim 1 , wherein
the at least one selected from R 11 to R 20 is selected from 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, an iso-pentyl group, a 1-methylbutyl group, a 2-methylbutyl group, a neo-pentyl group, a 1,2-dimethylpropyl group, and a tert-pentyl group, each substituted with a deuterium,
wherein selection of R 13 is subject to limitations of claim 1 .

10. The organometallic compound of claim 1 , wherein L 11 is a bidentate ligand.

11. The organometallic compound of claim 1 , wherein L 11 is represented by one of Formulae 4-1 to 4-4:

wherein in Formulae 4-1 to 4-4,
X 41 is selected from CR 41 and N;
X 42 is selected from CR 42 and N;
Y 41 and Y 42 are each independently selected from C and N;
A 41 to A 43 are each independently selected from 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, and a non-aromatic condensed heteropolycycle;
R 41 to R 44 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxy 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 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 41 )(Q 42 )(Q 43 );
b43 and b44 are each independently an integer selected from 1 to 5;

Assignees

• Samsung Electronics Co Ltd
• Samsung Sdi Co Ltd

Inventors

• Bae Hyejin
• Kim Wook
• Noh Changho
• Das Rupasree Ragini
• Rai Virendra Kumar
• Chae Miyoung
• Kravchuk Dmitry

Classifications

• C09K2211/1011

  Condensed systems · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• C09K2211/185

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

• H01L51/5016

  Electricity · mapped topic

• H01L51/0085 Primary

  Electricity · mapped topic