Blue emitter with high efficiency based on imidazo[1,2-f] phenanthridine iridium complexes

• US 8,815,415 B2
• Filed: 12/07/2009
• Issued: 08/26/2014
• Est. Priority Date: 12/12/2008
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Tsai, Jui-Yi, Yeager, Walter, Brooks, Jason, Beers, Scott, Kottas, Gregory S., Barron, Edward, Kwong, Raymond
• Primary Examiner(s): YAMNITZKY, MARIE ROSE
• Application Number:
  US12/632,251
• Publication Number:
  US 20100148663A1
• Time in Patent Office: 1,723 Days
• Field of Search: 548/108
• 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 2211/1044 containing two nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/1048 with oxygen
• CPC Class Codes: C09K 2211/1051 with sulfur
• CPC Class Codes: C09K 2211/185 of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
• CPC Class Codes: H05B 33/14 characterised by the chemical or physical composition or the arrangement of the electroluminescent material , or by the simultaneous addition of the electroluminescent material in or onto the light source
• 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
• CPC Class Codes: H10K 85/6572 comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
• CPC Class Codes: H10K 85/6576 comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene

Abstract

Imidazo[1,2-f]phenanthridine compounds are provided. The compounds have a twisted aryl moiety further substituted by alkyl having four or more atoms. The compounds may be used in organic light emitting devices, particularly as emissive dopants, providing devices with improved efficiency, stability, and manufacturing. In particular, the compounds provided herein may be used in blue devices having high efficiency.

Claims

1. A compound having the formula:

2. The compound of claim 1, wherein the alkyl having four or more atoms is a bicyclic alkyl.

3. The compound of claim 1, wherein the alkyl having four or more atoms is a multicyclic alkyl.

4. The compound of claim 1, wherein the alkyl having four or more atoms contains only carbon and hydrogen atoms.

5. The compound of claim 1, wherein at least one of R₁ and R₂ is a substituted heterocyclic alkyl that contains at least one of an oxygen atom, a nitrogen atom, or a sulfur atom, and wherein the at least one of an oxygen atom, a nitrogen atom, or a sulfur atom may be an attachment point.

6. The compound of claim 1, wherein R₁ and R₂ are the same.

7. The compound of claim 1, wherein R₁ and R₂ are different.

8. The compound of claim 1, wherein one of R₁ and R₂ is an aryl.

9. The compound of claim 1, wherein compound has the formula:

10. A compound selected from the group consisting of:

11. A compound including a ligand having the formula:

12. A first device comprising an organic light emitting device, comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, the organic layer comprising a compound having the formula;

13. The first device of claim 12, wherein the first device is a consumer product.

15. The first device of claim 12, wherein the organic layer is an emissive layer and the compound having the formula

16. The first device of claim 15, wherein the emissive layer comprises a host having the formula:

14. A first device comprising an organic light emitting device, comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, the organic layer comprising a compound selected from the group consisting of;