Metal complexes with boron-nitrogen heterocycle containing ligands

• US 8,586,203 B2
• Filed: 05/17/2010
• Issued: 11/19/2013
• Est. Priority Date: 05/20/2009
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Kwong, Raymond, Ma, Bin, Beers, Scott, Barron, Ed, Kottas, Gregg, Dyatkin, Alexey Borisovich, Tsai, Jui-Yi
• Primary Examiner(s): YAMNITZKY, MARIE ROSE
• Application Number:
  US12/781,493
• Publication Number:
  US 20100295032A1
• Time in Patent Office: 1,282 Days
• Field of Search: None
• US Class Current: 428/690
• CPC Class Codes: C07F 15/0033 Iridium compounds
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1007 Non-condensed systems
• CPC Class Codes: C09K 2211/1011 Condensed systems
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• CPC Class Codes: C09K 2211/104 with other heteroatoms
• CPC Class Codes: C09K 2211/1044 containing two nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/185 of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
• CPC Class Codes: H05B 33/10 Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/342 comprising iridium

Abstract

Novel organic compounds comprising ligands containing a boron-nitrogen heterocycle are provided. In particular, the compound is a metal complex comprising a ligand containing an azaborine. The compounds may be used in organic light emitting devices to provide devices having improved photophysical and electronic properties.

Claims

1. A compound comprising a monoanionic bidentate ligand L having the structure:

2. The compound of claim 1, wherein the ligand L is selected from the group consisting of:

3. The compound of claim 1, wherein the compound has the formula Mⁿ(L)_a(L′

)_b(L″

)_c;

wherein n is the oxidation state of the metal M;

wherein a is 1, 2, or 3;

wherein b is 0, 1, or 2;

wherein c is 0, 1, or 2;

wherein a+b+c is n; and

wherein L′ and

L″

are independently selected from the group consisting of;

4. The compound of claim 1, wherein the compound has the formula Mⁿ(L)_a(L′

)_b(L″

)_c;

wherein n is the oxidation state of the metal M;

wherein a is 1, 2, or 3;

wherein b is 0, 1, or 2;

wherein c is 0, 1, or 2;

wherein a+b+c is n; and

wherein L′ and

L″

are independently selected from the group consisting of;

5. The compound of claim 1, wherein the compound is selected from the group consisting of:

6. The compound of claim 5, wherein the compound is selected from the group consisting of:

7. An organic light emitting device comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, wherein the organic layer comprises a compound comprising a monoanionic bidentate ligand L having the structure;

8. The device of claim 7, wherein the ligand L is selected from the group consisting of:

9. The device of claim 7, wherein the compound has the formula Mⁿ(L)_a(L′

)_b(L″

)_c;

wherein n is the oxidation state of the metal M;

wherein a is 1, 2, or 3;

wherein b is 0, 1, or 2;

wherein c is 0, 1, or 2;

wherein a+b+c is n; and

wherein L′ and

L″

are independently selected from the group consisting of;

10. The device of claim 7,

wherein the compound is selected from the group consisting of:

11. The device of claim 7, wherein the organic layer is an emissive layer and the compound comprising the ligand L having FORMULA II is an emitting dopant;

and the organic layer further comprises a host containing a benzene, carbazole, dibenzofuran, dibenzothiophene, dibenzoselenophene, naphthalene, triphenylene, or biphenyl moiety.

12. A consumer product comprising a device, the device comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, wherein the organic layer comprises a compound comprising a monoanionic bidentate ligand L having the formula;