Organic electroluminescent materials and devices

• US 9,450,195 B2
• Filed: 12/17/2014
• Issued: 09/20/2016
• Est. Priority Date: 12/17/2014
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Tsai, Jui-Yi, Xia, Chuanjun
• Primary Examiner(s): Aulakh, Charanjit
• Application Number:
  US14/573,722
• Publication Number:
  US 20160181529A1
• Time in Patent Office: 643 Days
• Field of Search: 546/2, 313/504
• US Class Current: 1/1
• CPC Class Codes: C07F 15/0033 Iridium compounds
• CPC Class Codes: C07F 15/0086 Platinum compounds
• CPC Class Codes: C07F 17/02 of metals of Groups 8, 9 or 10 of the Periodic Table
• CPC Class Codes: C07F 19/00 Metal compounds according to more than one of main groups C07F1/00 - C07F17/00
• CPC Class Codes: C09K 11/025 non-luminescent particle coatings or suspension media
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1007 Non-condensed systems
• CPC Class Codes: C09K 2211/1022 bridged by heteroatoms, e.g. N, P, Si or B
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• CPC Class Codes: C09K 2211/1033 with oxygen
• CPC Class Codes: C09K 2211/1044 containing two nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/1088 containing oxygen as the only heteroatom
• CPC Class Codes: C09K 2211/185 of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 2101/30 Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values
• CPC Class Codes: H10K 2101/40 Interrelation of parameters between multiple constituent active layers or sublayers, e.g. HOMO values in adjacent layers
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/342 comprising iridium
• CPC Class Codes: H10K 85/344 comprising ruthenium
• CPC Class Codes: H10K 85/346 comprising platinum
• CPC Class Codes: H10K 85/348 : comprising osmium
• CPC Class Codes: H10K 85/361 : Polynuclear complexes, i.e. complexes comprising two or more metal centers
• CPC Class Codes: H10K 85/40 : Organosilicon compounds, e.g. TIPS pentacene
• CPC Class Codes: H10K 85/622 : containing four rings, e.g. pyrene
• CPC Class Codes: H10K 85/626 : containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
• CPC Class Codes: H10K 85/654 : comprising only nitrogen as heteroatom H10K85/652 takes precedence
• 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

Phosphorescent metal complexes comprising a pendant redox-active metallocene are disclosed. These complexes are useful as emitters for phosphorescent OLEDs.

Claims

1. A compound comprising a first ligand L¹ having the Formula:

2. The compound of claim 1, wherein at least one of R^A and R^B has a structure according to the following formula:

3. The compound of claim 1, wherein the ligand L¹ is

4. The compound of claim 1, wherein the compound is homoleptic.

5. The compound of claim 1, wherein the compound is heteroleptic.

6. The compound of claim 1, wherein the compound is neutral.

7. The compound of claim 1, wherein the ligand L¹ is selected from the group consisting of:

8. The compound of claim 1, wherein the compound has the formula of M(L¹)_x(L²)_y(L³)_z;

wherein L² is a second ligand, and L³ is a third ligand, and L² and L³ can be the same or different;

wherein x is 1, 2, or 3;

wherein y is 0, 1, or 2;

wherein z is 0, 1, or 2;

wherein x+y+z is the oxidation state of the metal M;

wherein the second ligand L² and the third ligand L³ are independently selected from the group consisting of;

9. The compound of claim 8, wherein the compound has the formula of Ir(L¹)(L²)₂.

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

16. A formulation comprising the compound of claim 1.

11. A device comprising one or more organic light emitting devices, at least one of the one or more organic light emitting devices comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, the organic layer comprising a compound comprising a first ligand L¹ of Formula I;

12. The device of claim 11, wherein the device is selected from the group consisting of a consumer product, an electronic component module, an organic light-emitting device, and a lighting panel.

13. The device of claim 11, wherein the organic layer is an emissive layer and the compound is an emissive dopant or a non-emissive dopant.

14. The device of claim 11, wherein the organic layer further comprises a host comprising at least one chemical group selected from the group consisting of carbazole, triphenylene, aza-triphenylene, dibenzothiphene, dibenzofuran, dibenzoselenophene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

15. The device of claim 11, wherein the organic layer further comprises a host selected from the group consisting of: