Organometallic compound and organic light-emitting diode comprising the same

Patent metadata

Field	Value
Publication number	US-9799839-B2
Application number	US-201314080471-A
Country	US
Kind code	B2
Filing date	Nov 14, 2013
Priority date	Dec 27, 2012
Publication date	Oct 24, 2017
Grant date	Oct 24, 2017

Abstract

An organometallic compound and an organic light-emitting diode (OLED) including the organometallic compound are provided. In exemplary embodiments, the organometallic compound is a platinum complex comprising one or two heterocyclic ligands, the heterocyclic ligands being the same or different if they are two in number, each heterocyclic ligand comprising two nitrogen heterocyclic rings connected by a single bond, one of the rings being six membered and comprising at least one nitrogen and the other ring being a 1,2-diazole or a 1,2,4-triazole ring. One or two other organic ligands may be attached to the central platinum atom in the complex. OLEDs including one of the subject platinum compounds in a light emission layer exhibit lower driving voltages, higher luminances, higher efficiencies and longer lifetimes than do comparative OLEDs built with established dopants incorporated into the light emitting layers.

First claim

What is claimed is:

1. An organometallic compound represented by Formula 1(1) below:

wherein, an Ax ring and an Ay ring in Formula 1(1) each being independently one of a 6-membered ring including at least one N, a 6-membered ring condensed with at least one 5-membered ring and including at least one N, and a 6-membered ring condensed with at least one 6-membered ring and including at least one N;
R 1x and R 1y in Formula 1(1) each being independently a substituted or unsubstituted linear or branched C 2 -C 60 alkyl group;
X 1x in Formula 1(1) being one of N and C(R 3x ), and X 1y in Formula 1(1) being one of N and C(R 3y );
R 2x to R 4x and R 2y to R 4y in Formula 1(1) each being independently selected from among a hydrogen atom, a deuterium atom, a halogen atom, a hydroxy group, a cyano group, a nitro group, an amidino group, a hydrazine, a hydrazone, a carboxyl 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 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 3 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -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 2 -C 60 heteroaryl group, —N(Q 1 )(Q 2 ), —Si(Q 3 )(Q 4 )(Q 5 ), and —C(═O)(Q 6 ) (where Q 1 to Q 6 are each independently one of a hydrogen atom, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 6 -C 60 aryl group, or a substituted or unsubstituted C 2 -C 60 heteroaryl group), R 3x and R 4x being optionally linked to each other to form one of a substituted or unsubstituted C 4 -C 20 alicyclic group, a substituted or unsubstituted C 2 -C 20 heteroalicyclic group, a substituted or unsubstituted C 6 -C 20 aromatic group and a substituted or unsubstituted C 2 -C 20 heteroaromatic group and R 3y and R 4y being optionally linked to each other to form one of a substituted or unsubstituted C 4 -C 20 alicyclic group, a substituted or unsubstituted C 2 -C 20 heteroalicyclic group, a substituted or unsubstituted C 6 -C 20 aromatic group and a substituted or unsubstituted C 2 -C 20 heteroaromatic group; and
a x and a y in Formula 1(1) each being independently an integer from 1 to 10.

2. The organometallic compound of claim 1 , the Ax ring and the Ay ring being each independently selected from among pyridine, pyrazine, pyrimidine, pyridazine, purine, isoquinoline, quinoline, phthalazine, 1,8-naphthyridine, quinoxaline, quinazoline, cinnoline, phenanthridine, 1,7-phenanthroline and pyrrolopyrimidine.

3. The organometallic compound of claim 1 , the Ax ring and the Ay ring being each independently selected from pyridine, pyrimidine, isoquinoline and quinazoline.

4. The organometallic compound of claim 1 , R 1x and R 1y being each independently selected from among:
an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, an i-butyl group, a t-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, and a decyl group; and
an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, an i-butyl group, a t-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, and a decyl group, each substituted with at least one of a deuterium atom, —F, a hydroxy group, a cyano group, a nitro group and an amino group.

5. The organometallic compound of claim 1 ,
X 1x being C(R 3x ), and X 1y being C(R 3y ); and
R 2x to R 4x and R 2y to R 4y being each independently one selected from among:
a hydrogen atom, a deuterium atom, a halogen atom, a hydroxy group, a cyano group, a nitro group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof;
a methyl group, an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, an i-butyl group, a t-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, and a pentoxy group; and
a methyl group, an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, an i-butyl group, a t-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, and a pentoxy group, each substituted with at least one of a deuterium atom, —F, a hydroxy group, a cyano group, a nitro group, and an amino group, R 3x and R 4x optionally linked to each other to form one of a substituted or unsubstituted C 4 -C 20 alicyclic group, a substituted or unsubstituted C 2 -C 20 heteroalicyclic group, a substituted or unsubstituted C 6 -C 20 aromatic group and a substituted or unsubstituted C 2 -C 20 heteroaromatic group, and R 3y and R 4y being optionally linked to each other to form one of a substituted or unsubstituted C 4 -C 20 alicyclic group, a substituted or unsubstituted C 2 -C 20 heteroalicyclic group, a substituted or unsubstituted C 6 -C 20 aromatic group and a substituted or unsubstituted C 2 -C 20 heteroaromatic group.

6. The organometallic compound of claim 1 , the organometallic compound being a compound represented by one of Formulae 1A to 1R below:

X 1x in Formulae 1A, 1B, 1G, 1H, 1M, and 1P being one of N and C(R 3x ), and X 1y in Formulae 1A, 1B, 1G, 1H, 1M, and 1P being one of N and C(R 3y );
R 1x and R 1y in Formulae 1A to 1R each being independently one selected from among:
an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, an i-butyl group, a t-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, and a decyl group; and
an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, an i-butyl group, a t-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, and a decyl group, each substituted with at least one of a deuterium atom, —F, a hydroxy group, a cyano group, a nitro group, and an amino group;
R 2x to R 4x , R 21x to R 28x , R 2y to R 4y , and R 21y to R 28y in Formulae 1A to 1R each being independently one selected from among:
a hydrogen atom, a deuterium atom, a halogen atom, a hydroxy group, a cyano group, a nitro group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof;
a methyl group, an ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, t-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, a methoxy group, an

Assignees

• Samsung Display Co Ltd
• Samsung Diplay Co Ltd

Inventors

• Choi Jong-Won
• Kwak Yoon-Hyun
• Park Bum-Woo
• Lee Sun-Young
• Choi Wha-Il
• Kim So-Yeon
• Lee Ji-Youn

Classifications

• C07F15/0093

  without a metal-carbon linkage · 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

• C09K2211/1059

  containing three nitrogen atoms as heteroatoms · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title