Organic electroluminescent material and devices

• US 9,630,983 B2
• Filed: 07/06/2015
• Issued: 04/25/2017
• Est. Priority Date: 09/03/2008
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Xia, Chuanjun, Alleyne, Bert, Kwong, Raymond C., Fiordeliso, James, Weaver, Michael S., Ansari, Nasrin, Deangelis, Alan, Rayabarapu, Dinesh, Adamovich, Vadim
• Primary Examiner(s): Aulakh, Charanjit
• Application Number:
  US14/791,741
• Publication Number:
  US 20150307535A1
• Time in Patent Office: 659 Days
• Field of Search: 546 2, 546 13, 544225
• 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 2211/1059 containing three nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/1066 with sulfur
• CPC Class Codes: C09K 2211/1074 containing more than three nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/1092 containing sulfur 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: 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 85/324 comprising aluminium, e.g. Alq3
• CPC Class Codes: H10K 85/342 comprising iridium
• CPC Class Codes: H10K 85/622 containing four rings, e.g. pyrene
• CPC Class Codes: H10K 85/633 comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: H10K 85/6576 comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
• CPC Class Codes: Y02E 10/549 Organic PV cells

Abstract

Novel organic compounds containing a twisted aryl group are provided. In particular, the compounds provided contain a 2-phenylpyridine ligand having a twisted aryl group on the pyridine portion of the ligand. The compounds may be used in organic light emitting devices, particularly as emitting dopants. Devices comprising the compounds containing twisted aryl may demonstrate improved color, efficiency, stability and manufacturing. Additionally, methods are provided for making homoleptic Ir (III) compounds which may contain a twisted aryl.

Claims

1. A method, comprising:

reacting

2. The method of claim 1, wherein X is selected from the group consisting of triflate, tosylate, trifluoroacetate, tetrafluoroborate, and hexafluorophosphate.

3. The method of claim 1, wherein R_A, R_B, R_C, and R_D are selected from the group consisting of benzene, pyrimidine, pyridine, thiophene, thianaphthene, fluorine, carbazole, and dibenzothiophene.

4. The method of claim 1, further comprising reacting

5. The method of claim 1, further comprising

reacting

6. The method of claim 1, further comprising

reacting

7. The method of claim 1, further comprising

reacting

8. The method of claim 1, further comprising

reacting

9. The method of claim 1, further comprising

reacting

10. The method of claim 1, further comprising:

reacting