Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-9312505-B2
Application number	US-201313787169-A
Country	US
Kind code	B2
Filing date	Mar 6, 2013
Priority date	Sep 25, 2012
Publication date	Apr 12, 2016
Grant date	Apr 12, 2016

Abstract

In certain embodiments, the invention provides metal complexes having Formula (I):

wherein each L x is independently a monodentate ligand, and any two adjacent L x may optionally combine to form a bidentate ligand; wherein M 1 is cobalt(I), rhodium(I), iridium(I), nickel(II), platinum(II), palladium(II), silver(III), gold(III), or copper(III); wherein m is a value from 1 to the maximum number of ligands that may be attached to M 1 ; wherein m+n is the maximum number of ligands that may be attached to M 1 ; wherein G 1 is O or CR 4 R 5 ; and R 1 to R 5 are various substituents, which can optionally combine with each other, among themselves, or with any L x . In certain embodiments, the invention provides devices, such as organic light emitting devices, that comprise such metal complexes.

First claim

We claim:

1. A compound having Formula (II):

wherein rings A 1 , A 2 , and A 3 are independently five- or six-membered carbocyclic or heterocyclic aromatic rings having 0-3 nitrogen atoms and 0-1 additional heteroatoms selected from the group consisting of oxygen, sulfur, and selenium;
Z 1 and Z 2 are independently carbon or nitrogen;
wherein R 2 represents mono- or di-substitution, wherein each R 2 is selected independently from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and wherein any two adjacent R 2 may optionally combine to form a ring, which can be further substituted;
wherein R 3 represents mono-, di-, tri-, or tetra-substitution, wherein each R 3 is selected independently from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and wherein any two adjacent R 3 may optionally combine to form a ring, which can be further substituted;
wherein G 1 is O or CR 4 R 5 ;
wherein R 4 and R 5 are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and wherein R 4 and R 5 may optionally combine to form a ring, which can be further substituted;
wherein any of R 4 or R 5 may optionally combine with any R 2 or R 3 to form a ring system, which can be further substituted;
wherein R 6 represents mono-, di-, or tri-substitution, wherein each R 6 is selected independently from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and wherein any two adjacent R 6 may optionally combine to form a ring, which can be further substituted;
wherein R 7 and R 8 represent mono-, di-, tri-, or tetra-substitution, wherein each R 7 or R 8 is selected independently from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and wherein any two adjacent R 7 or any two adjacent R 8 may optionally combine to form a ring, which can be further substituted;
wherein any R 3 may optionally combine with any R 6 to form a ring system, which can be further substituted;
wherein any R 2 may optionally combine with any R 8 to form a ring system, which can be further substituted; and
wherein any R 6 may optionally combine with any R 7 to form a ring system, which can be further substituted;
wherein any R 7 may optionally combine with any R 8 to form a ring system, which can be further substituted.

2. The compound of claim 1 , wherein G 1 is O , C(CH 3 ) 2 , or C(C 6 H 5 ) 2 .

3. The compound of claim 1 , which is a compound having Formula (IIa):

4. The compound of claim 1 , which is selected from the group consisting of:

5. A first device comprising a first organic light emitting device which comprises:
an anode;
a cathode; and
an organic layer disposed between the anode and the cathode,
the organic layer comprising a compound having Formula (II):

wherein rings A 1 , A 2 , and A 3 are independently five- or six-membered carbocyclic or heterocyclic aromatic rings having 0-3 nitrogen atoms and 0-1 additional heteroatoms selected from the group consisting of oxygen, sulfur, and selenium;
Z 1 and Z 2 are independently carbon or nitrogen;
wherein R 2 represents mono- or di-substitution, wherein each R 2 is selected independently from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and wherein any two adjacent R 2 may optionally combine to form a ring, which can be further substituted;
wherein R 3 represents mono-, di-, tri-, or tetra-substitution, wherein each R 3 is selected independently from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and wherein any two adjacent R 3 may optionally combine to form a ring, which can be further substituted;
wherein G 1 is O or CR 4 R 5 ;
wherein R 4 and R 5 are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and wherein R 4 and R 5 may optionally combine to form a ring, which can be further substituted;
wherein any of R 4 or R 5 may optionally combine with any R 2 or R 3 to form a ring system, which can be further substituted;
wherein R 6 represents mono-, di-, or tri-substitution, wherein each R 6 is selected independently from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and wherein any two adjacent R 6 may optionally combine to form a ring, which can be further substituted;
wherein R 7 and R 8 represent mono-, di-, tri-, or tetra-substitution, wherein each R 7 or R 8 is selected independently from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfi

Assignees

• Universal Display Corp

Inventors

• Brooks Jason
• Morello Glenn
• Xia Chuanjun
• Deng Jun

Classifications

• C09K11/025

  non-luminescent particle coatings or suspension media · CPC title

• 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

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title