ORGANIC ELECTROLUMINESCENT MATERIALS AND DEVICES

• US 20180134954A1
• Filed: 01/10/2018
• Published: 05/17/2018
• 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., OATE, Enrique, Esteruelas, Miguel A., BOUDREAULT, Pierre-Luc T., BAJO, Sonia, OLIVN, Montserrat
• Granted Patent: US 10,457,864 B2
• Time in Patent Office: Days
• 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

1-26. -26. (canceled)

27. 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, ligand L_A is

28. The method of claim 27, wherein rings A, B, C, and D each a ring independently selected from the group consisting of benzene, pyridine, imidazole, and pyrazole.

29. The method of claim 27, wherein M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu;

or M is Ir or Pt.

30. The method of claim 27, wherein L_C is

31. The method of claim 27, wherein L_C is

32. The method of claim 27, wherein L_C is

33. The method of claim 27, wherein X is chlorine.

34. The method of claim 33, wherein the precursor metal complex is

35. The method of claim 34, wherein the metal complex having the formula M(L_A)(L_B)(L_C) is selected from the group consisting of:

36. The method of claim 30, wherein the first reagent is a diketone compound having the formula

37. The method of claim 36, wherein R^X, R^Y, and R^Z are independently selected from the group consisting of hydrogen and alkyl.

38. The method of claim 36, wherein the precursor metal complex is

39. The method of claim 31, wherein the first reagent comprises

40. The method of claim 39, wherein the precursor metal complex is

41. The method of claim 32, comprising:

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

42. The method of claim 41, wherein the ancillary ligand is H₂O.

43. The method of claim 41, wherein M″

is boron.

44. The method of claim 41, wherein the precursor metal complex is

45. The method of claim 44, wherein the diketone compound is potassium acetylacetonate, the second reagent is HBF₄, and the compound comprising the formula M″

L_C″

is