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-2016233441-A1
Application number	US-201615013404-A
Country	US
Kind code	A1
Filing date	Feb 2, 2016
Priority date	Feb 6, 2015
Publication date	Aug 11, 2016
Grant date	—

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 selected from a first-row transition metal, a second-row transition metal, and a third-row transition metal;
R 11 to R 18 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —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, and 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 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 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 selected from a hydrogen, a deuterium, C 1 -C 30 alkyl group, and 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 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 M 11 is selected from Ir and Pt.

3 . The organometallic compound of claim 1 , wherein R 11 to R 18 are each independently selected from 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 C 6 -C 30 aryl group, and a substituted or unsubstituted C 1 -C 30 alkylsilyl group, wherein optionally, adjacent two of R 11 to R 15 are linked to form a substructure represented by Formula 10:

wherein, in Formula 10,
X 11 is selected from O, S, and N(R 105 );
R 101 to R 105 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a cyano group, 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 C 6 -C 30 aryl group, and a substituted or unsubstituted C 1 -C 30 alkylsilyl group; and
* and *′ are each independently a carbon atom to which adjacent two of R 11 to R 15 are bound.

4 . The organometallic compound of claim 1 , wherein R 11 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, a tert-pentyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, and —Si(Q 1 )(Q 2 )(Q 3 ), 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 at least one of a deuterium, —F, —Cl, —Br, —I, and a cyano group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, and a chrysenyl group, each substituted with at least one of 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 —Si(Q 4 )(Q 5 )(Q 6 ), wherein Q 1 to Q 3 are each independently 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; and Q 4 to Q 6 are each independently 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, 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 at least one of a deuterium, —F, —Cl, —Br, —I, and a cyano group, wherein at least one of Q 4 to Q 6 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

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

• C09K2211/185

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

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title

• B32B2457/206

  Organic displays, e.g. OLED · CPC title

• C09K11/025

  non-luminescent particle coatings or suspension media · CPC title