PHOSPHORESCENT MATERIALS

• US 20100090591A1
• Filed: 09/15/2009
• Published: 04/15/2010
• Est. Priority Date: 09/16/2008
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: YEAGER, Walter, ALLEYNE, Bert, KWONG, Raymond, XIA, Chuanjun
• Granted Patent: US 9,034,483 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: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 2102/00 Constructional details relating to the organic devices covered by this subclass
• CPC Class Codes: H10K 2102/103 comprising indium oxides, e.g. ITO
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/15 Hole transporting layers
• CPC Class Codes: H10K 50/16 Electron transporting layers
• CPC Class Codes: H10K 50/17 Carrier injection layers
• CPC Class Codes: H10K 50/81 Anodes
• CPC Class Codes: H10K 50/82 Cathodes
• CPC Class Codes: H10K 85/342 comprising iridium

Abstract

Phosphorescent materials and devices having high efficiency and stability, narrow spectrum, and improved processibility.

Claims

1. A compound having the formula:

wherein M is a metal of atomic weight higher than 40;

wherein A and B are each independently a 5 or 6-membered aromatic or heteroaromatic ring, and A-B represents a bonded pair of aromatic or heteroaromatic rings coordinated to the metal via a nitrogen atom on ring A and an sp² hybridized carbon atom on ring B;

wherein R_a, R_b, R_x, R_y, R_z are each independently selected from the group consisting of no substitution, alkyl, heteroalkyl, aryl, or heteroaryl groups;

wherein each of R_a and R_b represent one or more substituents and can join to form fused rings;

wherein at least one of R_x and R_y contains a branched alkyl moiety with branching at a position further than the α

position to the carbonyl group;

wherein m is the oxidation state of the metal; and

wherein n is an integer less than m and at least 1.

2. The compound of claim 1, wherein the compound is:

3. The compound of claim 1, wherein A-B is selected from the group consisting of:

wherein X is N—

R, O or S; and

wherein R is selected from the group consisting of hydrogen, alkyl, heteroalkyl, aryl, and heteroaryl groups.

4. The compound of claim 3, wherein the compound is:

5. The compound of claim 4, wherein R_x and R_y are an isobutyl group.

6. The compound of claim 5, wherein R_z is hydrogen.

7. The compound of claim 6, wherein the compound is selected from the group consisting of:

8. The compound of claim 5, wherein R_z is methyl.

9. The compound of claim 8, wherein the compound is:

10. A compound selected from the group consisting of:

11. The compound of claim 10, wherein the compound is selected from the group consisting of:

12. The compound of claim 10, wherein the compound is selected from the group consisting of:

13. The compound of claim 10, wherein the compound is selected from the group consisting of:

14. An organic, light emitting device comprising:

an anode;

a cathode; and

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

wherein M is a metal of atomic weight higher than 40;

wherein A and B are each independently a 5 or 6-membered aromatic or heteroaromatic ring, and A-B represents a bonded pair of aromatic or heteroaromatic rings coordinated to the metal via a nitrogen atom on ring A and an sp² hybridized carbon atom on ring B;

wherein R_a, R_b, R_x, R_y, R_z are each independently selected from the group consisting of no substitution, alkyl, heteroalkyl, aryl, or heteroaryl groups;

wherein each of R_a and R_b represent one or more substituents;

wherein at least one of R_x and R_y contains a branched alkyl moiety with branching at a position further than the α

position to the carbonyl group;

wherein m is the oxidation state of the metal; and

wherein n is an integer less than m and at least 1.

15. The device of claim 14, wherein the compound is:

16. The device of claim 15, wherein A-B is selected from the group consisting of:

wherein X is N—

R, O or S; and

wherein R is selected from the group consisting of no substitution, alkyl, heteroalkyl, aryl, and heteroaryl groups.

17. The device of claim 16, wherein the compound is:

18. The device of claim 17, wherein R_x and R_y are an isobutyl group.

19. The device of claim 18, wherein R_z is hydrogen.

20. The device of claim 19, wherein the compound is selected from the group consisting of:

21. The device of claim 18, wherein R_z is methyl.

22. The device of claim 21, wherein the compound is:

23. The device of claim 14, wherein the organic layer is an emissive layer comprising the compound and a host.

24. The device of claim 23, wherein the compound is the emissive material.

25. The device of claim 23, wherein the host is a metal coordination complex.

26. The device of claim 25, wherein the host is BAlq.

27. The device of claim 23, wherein the compound is the emissive material and the host is a metal coordination complex.

28. The device of claim 27, wherein the host is BAlq.

29. An organic light emitting device comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, the organic layer further comprising a compound selected from the group consisting of;

30. The device of claim 29, wherein the compound is selected from the group consisting of:

31. The device of claim 29, wherein the compound is selected from the group consisting of:

32. The device of claim 29, wherein the compound is selected from the group consisting of:

33. The device of claim 29, wherein the organic layer is an emissive layer comprising the compound and a host.

34. The device of claim 33, wherein the compound is the emissive material.

35. The device of claim 33, wherein the host is a metal coordination complex.

36. The device of claim 35, wherein the host is BAlq.

37. The device of claim 33, wherein the compounds is the emissive material and the host is a metal coordination complex.

38. The device of claim 37, wherein the host is BAlq.

39. A consumer product comprising a device, the device further comprising:

an anode;

a cathode; and

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

wherein M is a metal of atomic weight higher than 40;

wherein A and B are each independently a 5 or 6-membered aromatic or heteroaromatic ring, and A-B represents a bonded pair of aromatic or heteroaromatic rings coordinated to the metal via a nitrogen atom on ring A and an sp² hybridized carbon atom on ring B;

wherein R_a, R_b, R_x, R_y, R_z are each independently selected from the group consisting of no substitution, alkyl, heteroalkyl, aryl, or heteroaryl groups;

wherein each of R_a and R_b represent one or more substituents;

wherein at least one of R_x and R_y contains a branched alkyl moiety with branching at a position further than the α

position to the carbonyl group;

wherein m is the oxidation state of the metal; and

wherein n is at least 1.

40. A consumer product comprising a device, the device further comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, the organic layer further comprising a compound selected from the group consisting of;

41. A method comprising

42. The method of claim 41, further comprising

reacting

with a metal M and one or more ligands to form a compound having the formula:

wherein M is a metal of atomic weight higher than 40;

wherein A and B are each independently a 5 or 6-membered aromatic or heteroaromatic ring, and A-B represents a bonded pair of aromatic or heteroaromatic rings coordinated to the metal via a nitrogen atom on ring A and an sp² hybridized carbon atom on ring B;

wherein R_A and R_B each represent no substitution or one or more substituents;

wherein each substituent of R_A and R_B is independently selected from the group consisting of alkyl, heteroalkyl, aryl, or heteroaryl groups;

wherein m is the oxidation state of the metal; and

wherein n is an integer less than m and at least 1.

43. The compound of claim 41, wherein R_z is a methyl group;

and

wherein

44. An organometallic compound containing a structure selected from the group consisting of:

wherein M is a metal with an atomic weight greater than 40.

45. The compound of claim 44, wherein M is Ir.

46. The compound of claim 45, wherein the compound is a phosphorescent material.