Organic electroluminescent materials and devices

• US 10,457,864 B2
• Filed: 01/10/2018
• Issued: 10/29/2019
• Est. Priority Date: 02/09/2016
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Tsai, Jui-Yi, Xia, Chuanjun, Lin, Chun, Palacios, Adrian U., Onate, Enrique, Esteruelas, Miguel A., Boudreault, Pierre-Luc T., Bajo, Sonia, Olivan, Montserrat
• Primary Examiner(s): Vajda, Kristin A
• Application Number:
  US15/866,561
• Publication Number:
  US 20180134954A1
• Time in Patent Office: 657 Days
• Field of Search: 548103
• CPC Class Codes: C07F 15/0033 Iridium compounds
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• 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: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/12 comprising dopants
• CPC Class Codes: H10K 85/342 comprising iridium
• CPC Class Codes: H10K 85/626 containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
• CPC Class Codes: H10K 85/631 Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
• CPC Class Codes: H10K 85/654 comprising only nitrogen as heteroatom H10K85/652 takes precedence
• CPC Class Codes: H10K 85/657 Polycyclic condensed heteroaromatic hydrocarbons
• CPC Class Codes: H10K 85/6572 comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole

Abstract

Novel Iridium complexes having three different bidentate ligands useful for phosphorescent emitters in OLEDs are disclosed. At least one of the three different bidentate ligands is a carbene ligand.

Claims

1. A method of preparing a metal complex having the formula M(L_A)(L_B)(L_C), comprising:

providing a precursor metal complex having the formula (L_A)(L_B)M-(X)₂-M(L_A)(L_B),

wherein M is a metal selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu, ligand L_A is

2. The method of claim 1, wherein rings A, B, C, and D each a ring independently selected from the group consisting of benzene, pyridine, imidazole, and pyrazole.

3. The method of claim 1, wherein M is selected from the group consisting of Ir and Pt.

4. The method of claim 1, wherein L_C is

5. The method of claim 1, wherein L_C is

6. The method of claim 1, wherein L_C is

7. The method of claim 1, wherein X is chlorine.

8. The method of claim 7, wherein the precursor metal complex is

9. The method of claim 8, wherein the metal complex having the formula M(L_A)(L_B)(L_C) is selected from the group consisting of:

10. The method of claim 4, wherein the first reagent is a diketone compound having the formula

11. The method of claim 10, wherein R^X, R^Y, and R^Z are independently selected from the group consisting of hydrogen and alkyl.

12. The method of claim 10, wherein the precursor metal complex is

13. The method of claim 5, wherein the first reagent comprises

14. The method of claim 13, wherein the precursor metal complex is

15. The method of claim 6, comprising:

reacting the precursor metal complex with a diketone compound having the formula

16. The method of claim 15, wherein the ancillary ligand is H₂O.

17. The method of claim 15, wherein M″

is boron.

18. The method of claim 15, wherein the precursor metal complex is

19. The method of claim 18, wherein the diketone compound is potassium acetylacetonate, the second reagent is HBF₄, and the compound comprising the formula M″

L_C″

is