OLEDs utilizing multidentate ligand systems

• US 7,332,232 B2
• Filed: 06/03/2004
• Issued: 02/19/2008
• Est. Priority Date: 02/03/2004
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Ma, Bin, Kwong, Raymond, Walters, Robert, Brooks, Jason
• Primary Examiner(s): YAMNITZKY, MARIE ROSE
• Application Number:
  US10/859,796
• Publication Number:
  US 20050170207A1
• Time in Patent Office: 1,356 Days
• Field of Search: None
• US Class Current: 428/690
• CPC Class Codes: C07F 15/0033 Iridium compounds
• CPC Class Codes: C07F 15/0073 Rhodium compounds
• CPC Class Codes: C07F 5/069 without C-aluminium linkages
• 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 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 85/324 comprising aluminium, e.g. Alq3
• 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 85/649 Aromatic compounds comprising a hetero atom
• CPC Class Codes: Y10S 428/917 Electroluminescent

Abstract

An organic light emitting device is provided. The device has an anode, a cathode, and an organic layer disposed between the anode and the cathode. The organic layer comprises an emissive material having a transition metal and two or three bidentate ligands, which may be photoactive ligands. The bidentate photoactive ligands may be bound to the transition metal through a carbon-metal bond and a nitrogen-metal bond to form a cyclometallated ring. The organic layer may have the formula LX_a-(L)_bM, wherein X is a linking group that links two or more ligand L and M is a metal.

Claims

1. An organic light emitting device comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a phosphorescent organometallic emissive material comprising

a transition metal, Tl, Pb, Bi, In, Sn, Sb or Te, and

two or three bidentate ligands, wherein two or more of the bidentate ligands are covalently linked by a linking group,

wherein, the bidentate ligands are selected from bidentate photoactive ligands, wherein each bidentate photoactive ligand is bound to the transition metal, Tl, Pb, Bi, In, Sn, Sb or Te through a carbon-metal bond and a nitrogen-metal bond to form a cyclometallated ring, and bidentate ancillary ligands,

wherein at least one of the bidentate ligands is a bidentate photoactive ligand.

2. The organic light emitting device of claim 1, wherein the linking group provides no π

-conjugation between the linked bidentate ligands.

3. The organic light emitting device of claim 1 wherein the transition metal is selected from the group consisting of Ir, Pt, Pd, Rh, Re, Os, Au, and Ag.

4. The organic light emitting device of claim 1 wherein the transition metal is Ir.

5. An organic light emitting device comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises an emissive material of the formula I

[X_a—

(L)_b]M 

 

(I)

wherein

M is a transition metal having a molecular weight greater than 40, Tl, Pb, Bi, In, Sn, Sb or Te;

X is a linking group that links two or more L, and is selected from the group consisting of —

(CR₂)_d—

, —

[O(CR₂)_e]O—

, or a group having the formula

6. The organic light emitting device of claim 5, wherein the photoactive ligands are selected from compounds of the formula IV

7. The organic light emitting device of claim 5, wherein [X_a—

(L)_b] has the formula;

8. The organic light emitting device of claim 5, wherein the emissive material is a compound having the formula

9. The organic light emitting device of claim 5, wherein the emissive material is a compound having the formula

10. The organic light emitting device of claim 5, wherein the emissive material is a compound having the formula

11. The organic light emitting device of claim 5, wherein [X_a—

(L)_b] has the formula;

12. The organic light emitting device of claim 5, wherein [X_a—

(L)_b] has the formula;

13. The organic light emitting device of claim 5, wherein [X_a—

(L)_b] has the formula;

14. The organic light emitting device of claim 5, wherein the emissive material is a compound having the formula

15. The organic light emitting device of claim 5, wherein the emissive material is a compound having the formula:

16. The organic light emitting device of claim 5, wherein two or more L comprise a phenyl moiety and X is a linking group that links the two or more L via a covalent bond to the phenyl moiety in each of the two or more L.

17. The organic light emitting device of claim 5, wherein [X_a—

(L)_b] has the formula

18. The organic light emitting device of claim 17, wherein [X_a—

(L)_b] has the formula;

19. The organic light emitting device of claim 17, wherein [X_a—

(L)_b] has the formula;

20. The organic light emitting device of claim 5 wherein the transition metal is selected from the group consisting of Ir, Pt, Pd, Rh, Re, Os, Au, and Ag.

21. The organic light emitting device of claim 5 wherein the transition metal is Ir.

22. A compound of the formula I

[X_a—

(L)_b]M 

 

(I)

wherein,

M is a transition metal having a molecular weight greater than 40, Tl, Pb, Bi, In, Sn, Sb or Te;

X is a linking group that links two or more L, and is selected from the group consisting of —

(CR₂)_d—

, —

[O(CR₂)_e]O—

, or a group having the formula

23. The compound of claim 22, wherein the photoactive ligands are selected from compounds of the formula IV

24. The compound of claim 22, wherein [X_a—

(L)_b] has the formula;

25. The compound of claim 22, having the formula

26. The compound of claim 22, having the formula

27. The compound of claim 22, having the formula

28. The compound of claim 22, wherein [X_a—

(L)_b] has the formula;

29. The compound of claim 22, wherein [X_a—

(L)_b] has the formula;

30. The compound claim 22, wherein [X_a—

(L)_b] has the formula;

31. The compound of claim 22, having the formula:

32. The compound of claim 22 having the formula:

33. The compound of claim 22, wherein X is linked to each L via a covalent bond to a pyridyl moiety in each L.

34. The compound of claim 22, wherein [X_a—

(L)_b] has the formula;

35. The compound of claim 34, wherein [X_a—

(L)_b] has the formula;

36. The compound of claim 34, wherein [X_a—

(L)_b] has the formula;

37. The compound of claim 22 wherein the transition metal is selected from the group consisting of Ir, Pt, Pd, Rh, Re, Os, Au, and Ag.

38. The compound of claim 22 wherein the transition metal is Ir.

39. An organic light emitting device comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a metal complex comprising:

a metal;

a first ligand bound to the metal, wherein the first ligand is a bidentate ligand;

a second ligand bound to the metal; and

a linking group that covalently links the first ligand and the second ligand,

wherein the linking group provides no iL-conjugation between the first ligand and the second ligand;

and wherein the metal complex is a phosphorescent organometallic emissive material.

40. The organic light emitting device of claim 39, wherein the second ligand is a monodentate ligand.

41. An organic light emitting device comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a phosphorescent organometallic emissive material comprising a metal bound to two or three bidentate ligands, wherein two or more of the bidentate ligands are covalently linked by one or more linking groups.

42. The organic light emitting device of claim 41 wherein the organometallic emissive material comprises a compound represented by the formula

[X_a—

(L)_bM

wherein M is a transition metal, Tl, Pb, Bi, In, Sn, Sb, or Te;

L is a bidentate ligand;

X is a linking group that links two or more L;

a is 1 to 4;

b is 2 or 3;

wherein the bidentate ligands are selected from bidentate photoactive ligands, and bidentate ancillary ligands wherein at least one of the bidentate ligands is a bidentate photoactive ligand.

43. The organic light emitting device of claim 42 wherein the transition metal is selected from the group consisting of Ir, Pt, Pd, Rh, Re, Os, Au, and Ag.

44. The organic light emitting device of claim 42 wherein the transition metal is Ir.

45. A compound of the formula

[X_a—

(L)_b]M

wherein M is a transition metal, Tl, Pb, Bi, In, Sn, Sb or Te;

L is a bidentate ligand;

X is a linking group that links two or more L;

a is 1 to 4,

b is 2 or 3

wherein the bidentate ligands are selected from bidentate photoactive ligands, and bidentate ancillary ligands wherein at least one of the bidentate ligands is a bidentate photoactive ligand bound to the transition metal, Tl, Pb, Bi, In, Sn. Sb or Te through a carbon-metal bond; and

wherein the compound is a phosphorescent emissive material.

46. The compound of claim 45 wherein the transition metal is selected from the group consisting of Ir, Pt, Pd, Rh, Re, Os, Au, and Ag.

47. The compound of claim 45 wherein the transition metal is Ir.