Ion-Pairing Soft Salts Based On Organometallic Complexes And Their Applications In Organic Light Emitting Diodes

• US 20110101856A1
• Filed: 11/01/2010
• Published: 05/05/2011
• Est. Priority Date: 11/02/2009
• Status: Active Grant

• Current Assignee: University of Southern California
• Original Assignee: University of Southern California
• Inventors: Chen, Hsiao-Fan, Wu, Chao, Thompson, Mark E.
• Granted Patent: US 8,545,996 B2
• Time in Patent Office: Days
• US Class Current: 313/504
• 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 2211/185 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 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/1135 Polyethylene dioxythiophene [PEDOT]; Derivatives thereof
• CPC Class Codes: H10K 85/322 comprising boron
• CPC Class Codes: H10K 85/342 comprising iridium
• 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 85/633 comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom

Abstract

Organometallic soft salt compounds are provided. In particular, the compounds comprise mononuclear Ir-based soft salts. The compounds may be used in organic light emitting diodes (OLED) and light emitting cells (LEC).

Claims

1. A compound comprising the formula:

2. The compound of claim 1, wherein M_i and M_j are Ir.

3. The compound of claim 1, wherein M_i and M_j are Ir(III).

4. The compound of claim 1, wherein the compound has the formula:

5. The compound of claim 1, wherein the organometallic cation has the formula:

6. The compound of claim 5, wherein

7. The compound of claim 5, wherein each

8. The compound of claim 1, wherein each of L_i and L_j are independently selected from the group consisting of:

9. The compound of claim 8, wherein each of L_i and L_j are independently selected from the group consisting of:

10. The compound of claim 1, wherein all of the organometallic cations are the same and all of the organometallic anions are the same.

11. The compound of claim 1, wherein the organometallic anion is selected from the group consisting of:

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

13. An organic light emitting device comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, further comprising a compound comprising the formula;

14. The device of claim 13, wherein M_i and M_j are Ir.

15. The device of claim 13, wherein M_i and M_j are Ir(III).

16. The device of claim 13, wherein the compound has the formula:

17. The device of claim 13, wherein the organometallic cation has the formula:

18. The device of claim 17, wherein

19. The device of claim 17, wherein each

20. The compound of claim 13, wherein each of L_i and L_j are independently selected from the group consisting of:

21. The compound of claim 20, wherein each of L_i and L_j are independently selected from the group consisting of:

22. The device of claim 13, wherein all of the organometallic cations are the same and all of the organometallic anions are the same.

23. The device of claim 13, wherein the organometallic anion is selected from the group consisting of:

24. The device of claim 13, wherein the compound is selected from the group consisting of:

25. The device of claim 13, wherein the organic layer is deposited using vapor disposition.

26. The device of claim 13, wherein one of the organometallic anion and the organometallic cation has both a lower oxidation potential and a less negative reduction potential than the other.

27. The device of claim 13, wherein PVK is mixed with dichlorobenzene and deposited prior to depositing the organic layer.

28. The device of claim 27, wherein a film comprising BCP is deposited over the organic layer.

29. A method, comprising:

obtaining an organometallic complex comprising the formula;

30. The method of claim 29, wherein the organometallic cation and the organometallic anion are obtained by:

reacting

31. A method, comprising:

reducing an organometallic cation having the formula;

C_i^ai+ to be neutral,

oxidizing an organometallic anion having the formula;

C_j^bj−

to be neutral, and

reacting the two neutral species to form an organometallic complex comprising the formula;

32. The method of claim 31, wherein the neutral metallated complexes are thermally vacuum deposited in combination onto a substrate wherein the reaction is completed to obtain the organometallic complex.

33. The method of claim 31, further comprising:

providing a first electrode;

depositing the organometallic cation and the organometallic anion over the first electrode; and

depositing a second electrode.

34. The method of claim 33, wherein the first electrode is an anode and the second electrode is a cathode.