Organic light emitting materials with anionic ligand

• US 20040102632A1
• Filed: 08/18/2003
• Published: 05/27/2004
• Est. Priority Date: 08/16/2002
• Status: Active Grant

• Current Assignee: University of Southern California
• Original Assignee: University of Southern California
• Inventors: Thompson, Mark E., Li, Jian, Djurovich, Peter
• Granted Patent: US 7,482,451 B2
• Time in Patent Office: Days
• US Class Current: 546/2
• CPC Class Codes: C07F 15/0033 Iridium compounds
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1022 bridged by heteroatoms, e.g. N, P, Si or B
• 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 85/311 Phthalocyanine
• CPC Class Codes: H10K 85/321 Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
• CPC Class Codes: H10K 85/322 comprising boron
• CPC Class Codes: H10K 85/324 comprising aluminium, e.g. Alq3
• CPC Class Codes: H10K 85/341 Transition metal complexes, e.g. Ru(II)polypyridine complexes H10K85/331 takes precedence
• CPC Class Codes: H10K 85/342 comprising iridium
• CPC Class Codes: H10K 85/633 comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom

Abstract

Emissive phosphorescent organometallic compounds that produce electroluminescence and organic light emitting devices employing such emissive phosphorescent organometallic compounds are provided. More specifically the present invention is directed to novel primarily non-emitting ligands which produce a blue shift in emitted light when associated with a cyclometallated ligand.

Claims

1. A compound represented by the Formula (I)

2. The compound of claim 1, wherein J is boron.

3. The compound of claim 1 wherein the heteroatom-containing group is selected from OR, SR, NR₂ and PR₂, wherein R is alkyl, aryl, or heteroaryl.

4. The compound of claim 3, wherein R is a C₁-C₆ alkyl, aryl, or heteroaryl.

5. The compound of claim 1, wherein R′

and R″

are heteroaryl.

6. The compound of claim 5 wherein R′

and R″

are selected from the group consisting of alkyls, aryls, and pyrazoles and p and q are each 1.

7. The compound of claim 4 wherein R′

is pyrazole, R″

is a pyrazole and p and q are each 1.

8. The compound of claim 5 wherein X and Y are pyrazoles.

9. The compound of claim 5, wherein Z is hydrogen.

10. The compound of claim 1, wherein the heavy metal is selected from the group consisting of Ir, Pt, Pd, Rh, Re, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Ag, and Au.

11. The compound of claim 9 wherein the heavy metal is Ir.

12. The compound of claim 9 wherein the heavy metal is Pt.

13. The compound of claim 1, having the Formula III:

14. The compound of claim 5, having the formula IV:

15. The compound of claim 1, having the Formula V:

16. A compound represented by the formula (I)

17. The compound of claim 16, wherein X and Y are heterocycles.

18. The compound of claim 17 wherein X and Y are pyrazoles.

19. The compound of claim 18 wherein R′

is pyrazole, R″

is a pyrazole and p and q are each 1.

20. The compound of claim 16 wherein R′

is selected from the group consisting of bidentate alkyl, aryl and carboxyl ligands and chelating coordination ligands, p is equal to 1 and q is equal to 0.

21. The compound of claim 16 wherein R′

and R″

are selected from the group consisting of alkyls, aryls, and pyrazoles and p and q are each 1.

22. The compound of claim 16, wherein Z is hydrogen.

23. The compound of claim 16, wherein the heavy metal is selected from the group consisting of Ir, Pt, Pd, Rh, Re, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Ag, and Au.

24. The compound of claim 23 wherein the heavy metal is Ir.

25. The compound of claim 23 wherein the heavy metal is Pt.

26. The compound of claim 16 having the formula (II).

27. A light emitting device comprising an organic layer, the organic layer comprising a composition represented by the structure:

28. The light emitting device of claim 27, wherein Z is represented by the general structure JR′

_pR″

_q wherein J is hydrogen, a metal or a non-metal, R′ and

R″

are independently H, alkyl, alkenyl, aryl, heteroaryl, halogen, hydroxy, alkoxy, aryloxy, amino, alkylamino, arylamino, sulfido, alkylsulfido, arylsulfido, phophino, alkylphosphino or arylphosphino and p and q are integers between 0 and 2.

29. The light emitting device of claim 28 wherein J is selected from the group consisting of H, Ag, Zn, Al, B, Ga, In, Cd, Hg, Cu, Au.

30. The light emitting device of claim 27, wherein X and Y are heterocycles.

31. The light emitting device of claim 30 wherein X and Y are pyrazoles.

32. The light emitting device of claim 28, wherein J is boron.

33. The light emitting device of claim 32, wherein X and Y are both pyrazoles.

34. The light emitting device of claim 33 wherein R′

is pyrazole, b is equal to 0 and a is equal to 2.

35. The light emitting device of claim 28 wherein R′

is selected from the group consisting of bidentate alkyl, aryl and carboxyl ligands and chelating coordination ligands, b is equal to 0 and a is equal to 1.

36. The light emitting device of claim 27 wherein R′

and R″

are selected from the group consisting of alkyls, aryls, and pyrazoles and p and q are each equal to 1.

37. The light emitting device of claim 27, wherein Z is hydrogen.

38. The light emitting device of claim 37, wherein X and Y are pyrazoles.

39. The light emitting device of claim 27, wherein the heavy metal is selected from the group consisting of Ir, Pt, Pd, Rh, Re, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Ag, Au.

40. The light emitting device of claim 39 wherein the heavy metal is Ir.

41. The light emitting device of claim 39 wherein the heavy metal is Pt.

42. The light emitting device of claim 27 wherein at least one of X and Y is selected from the group consisting of OR, SR, NR₂, PR₂.

43. The light emitting device of claim 49, wherein R is selected from the group consisting of H, alkyl, aryl, heteroaryl, halogen, alkoxy, amino, alkylamino, arylamino, sulfido, alkylsulfido, arylsulfido, phophino, alkylphosphino or arylphosphino.