Organic light emitting materials and devices

• US 6,687,266 B1
• Filed: 11/08/2002
• Issued: 02/03/2004
• Est. Priority Date: 11/08/2002
• Status: Expired due to Term

• Current Assignee: Universal Display Corporation, University of Southern California
• Original Assignee: Universal Display Corporation, University of Southern California
• Inventors: Knowles, David B., Ma, Bin, Thompson, Mark E., Brown, Cory S., Murphy, Drew
• Primary Examiner(s): Scott, Jr., Leon
• Application Number:
  US10/291,338
• Time in Patent Office: 452 Days
• Field of Search: 372/7, 372/39, 428/690, 428/432, 257/141, 438/144, 438/745, 427/66, 427/64, 430/200, 313/504, 313/506
• US Class Current: 372/7
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• 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: 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 85/342 comprising iridium

Abstract

An organic light emitting device is provided. The device includes an anode, a cathode, and an emissive layer disposed between the anode and the cathode. The emissive layer includes material having the structure:

M is a metal having an atomic weight greater than 40, m is at least 1, n is at least zero, R″ is H or any substituent, X is an ancillary ligand, and A is selected from the group consisting of aryl and heteroaryl rings, and B is an aryl ring. A material including the photoactive ligand of the above material is also provided.

Claims

1. An organic light emitting device, comprising:

(a) an anode;

(b) a cathode; and

(c) an emissive layer disposed between the anode and the cathode, the emissive layer including a material having a ligand having the structure;

wherein the ligand is attached to a metal having an atomic weight greater than 40, and A is selected from the group consisting of aryl and heteroaryl rings, and B is an aryl ring, and R″

is selected from the group consisting of hydrogen and any substituent.

2. The device of claim 1, wherein the emissive layer includes a material having the structure:

wherein M is a metal having an atomic weight greater than 40, in is at least 1, n is at least zero, R″

is hydrogen or any substituent, X is an ancillary ligand, and A is selected from the group consisting of aryl and heteroaryl rings, and B is an aryl ring.

3. The device of claim 2, wherein at least one of A and B includes a substituent.

4. The device of claim 2, wherein M is selected from the group consisting of Ir, Pt, Pd, Rh, Re, Ru, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au, and Ag.

5. The device of claim 4, wherein m is 2, and wherein n is 1.

6. The device of claim 2, wherein M is Ir.

7. The device of claim 2, wherein M is Pt.

8. The device of claim 2, wherein n is zero.

9. The device of claim 2, wherein the emissive material is incorporated into a polymer.

10. The device of claim 2, wherein the emissive material is incorporated into a dendrimer.

11. The device of claim 2, wherein the emissive layer further comprises a host material.

12. The device of claim 11, wherein the emissive material is a dopant in the host material.

13. The device of claim 2, wherein the emissive material consists essentially of a neat film of the emissive material.

14. The device of claim 2, wherein the emissive layer includes a material having the structure:

wherein;

Y is C; and

R2, R3, R4, R5, R′

2, R′

3, R′

4, and R′

5 are each independently selected from the group consisting of hydrogen and any substituent.

15. The device of claim 14, wherein R2, R3, R4, R5, R′

2, R′

3, R′

4 and R′

5 are each a hydrogen atom, R″

is —

CH₃, and X is acac.

16. The device of claim 14, wherein at least one of the groups R2, R3, R4, R5, R′

2, R′

3, R′

4 and R′

5 is linked to another of the groups R2, R3, R4, R5, R′

2, R′

3, R′

4 and R′

5 to form a ring.

17. The device of claim 2, wherein:

the emissive layer includes a material having the structure;

18. The device of claim 2, wherein the device has a luminous efficiency of at least 22.5 cd/A, at a luminance of 500 cd/m².

19. An emissive material having a ligand having the structure:

wherein the ligand is attached to a metal having an atomic weight greater than 40, and A is selected from the group consisting of aryl and heteroaryl rings, and B is an aryl ring, and R″

is selected from the group consisting of hydrogen and any substituent.

20. The emissive material of claim 19, wherein the material has the structure:

wherein M is a metal having an atomic weight greater than 40, m is at least 1, n is at least zero, R″

is hydrogen or any substituent, X is an ancillary ligand, and A is selected from the group consisting of aryl and heteroaryl rings, and B is an aryl ring.

21. The emissive material of claim 20, wherein at least one of A and B includes a substituent.

22. The emissive material of claim 20, wherein M is selected from the group consisting of Ir, Pt, Pd, Rh, Re, Ru, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au, and Ag.

23. The emissive material of claim 22, wherein m is 2, and wherein n is 1.

24. The emissive material of claim 20, wherein M is Ir.

25. The emissive material of claim 20, wherein M is Pt.

26. The emissive material of claim 20, wherein n is zero.

27. The emissive material of claim 20, wherein the emissive material is incorporated into a polymer.

28. The emissive material of claim 20, wherein the emissive material is incorporated into a dendrimer.

29. The emissive material of claim 20, wherein the emissive layer further comprises a host material.

30. The emissive material of claim 29, wherein the emissive material is a dopant in the host material.

31. The emissive material of claim 20, wherein the emissive material consists essentially of a neat film of the emissive material.

32. The emissive material of claim 20, wherein the emissive layer includes a material having the structure:

wherein;

M is Ir;

Y is C; and

R2, R3, R4, R5, R′

2, R′

3, R′

4, and R′

5 are each independently selected from the group consisting of hydrogen and any substituent.

33. The emissive material of claim 32, wherein R2, R3, R4, R5, R′

2, R′

3, R′

4 and R′

5 are each a hydrogen atom, R″

is —

CH₃, and X is acac.

34. The emissive material of claim 32, wherein at least one of the groups R2, R3, R4, R5, R′

2, R′

3, R′

4 and R′

5 is linked to another of the groups R2, R3, R4, R5, R′

2, R′

3, R′

4 and R′

5 to form a ring.

35. The emissive material of claim 20, wherein the emissive material has the structure: