Metal-assisted delayed fluorescent emitters containing tridentate ligands

• US 9,818,959 B2
• Filed: 07/27/2015
• Issued: 11/14/2017
• Est. Priority Date: 07/29/2014
• Status: Active Grant

• Current Assignee: Arizona Board of Regents (University of Arizona)
• Original Assignee: Arizona Board of Regents (University of Arizona)
• Inventors: Li, Jian, Li, Guijie
• Primary Examiner(s): Aulakh, Charanjit
• Application Number:
  US14/809,981
• Publication Number:
  US 20160043331A1
• Time in Patent Office: 841 Days
• Field of Search: 546 2, 313504
• CPC Class Codes: C07F 1/12 Gold compounds
• CPC Class Codes: C07F 15/0033 Iridium compounds
• CPC Class Codes: C07F 15/006 Palladium compounds
• CPC Class Codes: C07F 15/0073 Rhodium compounds
• CPC Class Codes: C07F 15/0086 Platinum compounds
• CPC Class Codes: C07F 9/65683 the ring phosphorus atom being part of a phosphine
• CPC Class Codes: C07F 9/65685 the ring phosphorus atom being part of a phosphine oxide or thioxide
• 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 2211/1014 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 2211/1048 with oxygen
• CPC Class Codes: C09K 2211/1059 containing three nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/1088 containing oxygen as the only heteroatom
• CPC Class Codes: C09K 2211/1092 containing sulfur as the only heteroatom
• CPC Class Codes: C09K 2211/1096 containing other heteroatoms
• 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 85/346 : comprising platinum

Abstract

Tridentate platinum, palladium, and gold complexes of Formulas A-I and A-II and tridentate iridium and rhodium compounds of Formulas B-I, B-II, and B-III suitable for delayed fluorescent and phosphorescent or phosphorescent emitters in display and lighting applications.

Claims

1. A compound represented by Formula A-1:

2. The compound of claim 1, wherein M-R^L4 is one of:

3. The compound of claim 1, wherein the five-membered heterocyclyl

4. The compound of claim 1, wherein:

5. The compound of claim 1, wherein each of LP¹, LP² and LP³, if present, independently represents one of the following structures:

aromatic hydrocarbons selected from the group consisting of;

6. The compound of claim 1, wherein each LP¹, LP² and LP³, if present, is independently bonded indirectly to L¹, L², or L³, respectively, through a linking atom or linking group selected from the group consisting of:

7. The compound of claim 1, wherein M is Pt.

8. The compound of claim 1, wherein L¹ is a five-membered heterocyclyl, five-membered heteroaryl, five-membered carbene, or five-membered N-heterocyclic carbene.

9. The compound of claim 1, wherein L¹ is a five-membered heterocyclyl or five-membered heteroaryl.

10. The compound of claim 1, wherein L¹ is pyrazolyl or imidazolyl.

11. The compound of claim 1, wherein LP¹ is present, and LP² and LP³ are absent.

12. The compound of claim 1, wherein LP¹ is present and is an aromatic hydrocarbon, an aromatic hydrocarbon derivative, a polyphenyl hydrocarbon, a hydrocarbon with condensed aromatic nuclei, naphthalene, anthracene, phenanthrene, chrysene, pyrene, triphenylene, perylene, acenaphthene, tetracene, pentacene, tetraphene, coronene, fluorene, biphenyl, p-terphenyl, o-diphenylbenzene, m-diphenylbenzene, p-quaterphenyl, benzo[a]tetracene, benzo[k]tetraphene, indeno[1,2,3-cd]fluoranthene, or tetrabenzo[de,hi,op,st]pentacene.

13. The compound of claim 1, wherein LP¹ is present and is an aromatic hydrocarbon.

14. The compound of claim 5, wherein LP¹ is present and is

15. The compound of claim 1, wherein V¹ is independently N or C.

16. The compound of claim 1, wherein each of Y¹, Y², Y³, and Y⁴ is independently C or N.

17. The compound of claim 1, wherein the compound is selected from:

18. The compound of claim 1, wherein the compound is a delayed fluorescent and phosphorescent emitter, a phosphorescent emitter, or a delayed fluorescent emitter.

19. A device comprising the compound of claim 1, wherein the device is an organic light emitting diode or a full color display.

20. The compound of claim 1, wherein the compound is selected from: