Triphenylene hosts in phosphorescent light emitting diodes

• US 20060280965A1
• Filed: 05/31/2006
• Published: 12/14/2006
• Est. Priority Date: 05/31/2005
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Kwong, Raymond, Alleyne, Bert
• Granted Patent: US 8,092,924 B2
• Time in Patent Office: Days
• US Class Current: 428/690
• CPC Class Codes: C07C 13/62 with more than three condensed rings
• CPC Class Codes: C07C 15/38 containing four rings
• CPC Class Codes: C07C 2603/42 containing only six-membered rings
• CPC Class Codes: C07C 2603/54 containing more than five condensed rings
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 19/32 containing condensed ring systems, i.e. fused, bridged or spiro ring systems
• CPC Class Codes: C09K 2019/328 containing a triphenylene ring system
• CPC Class Codes: C09K 2211/1007 Non-condensed systems
• CPC Class Codes: C09K 2211/1011 Condensed systems
• CPC Class Codes: C09K 2211/1416 Condensed systems
• 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 71/16 using physical vapour deposition [PVD], e.g. vacuum deposition or sputtering
• CPC Class Codes: H10K 85/622 containing four rings, e.g. pyrene
• CPC Class Codes: H10K 85/624 containing six or more rings
• CPC Class Codes: H10K 85/625 containing at least one aromatic ring having 7 or more carbon atoms, e.g. azulene
• CPC Class Codes: H10K 85/626 containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
• CPC Class Codes: Y10S 428/917 Electroluminescent

Abstract

An organic emissive layer is provided. Also provided is a device in which the organic emissive layer is disposed between an anode and a cathode. The organic emissive layer includes a phosphorescent material and triphenylene compound or a compound having a repeat unit having a triphenylene moiety. The triphenylene is optionally substituted. The substituents may be the same or different and each is selected from the group consisting of alkyl, aryl, fused aryl, substituted aryl, alkenyl, alkynyl, and heteroalkyl. Triphenylene compounds are also provided.

Claims

1. An emissive layer comprising a phosphorescent material and a triphenylene compound having the formula

2. The emissive layer of claim 1 wherein at least one of R₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈, R₉, R₁₀, R₁₁, and R₁₂ is selected from aryl and substituted aryl.

3. The emissive layer of claim 1 wherein R₁, R₄, R₅, R₈, R₉, and R₁₂ are all H, and each of R₂, R₃, R₆, R₇, R₁₀, and R₁₁ is independently selected from aryl and substituted aryl.

4. The emissive layer of claim 3 wherein R₂, R₃, R₆, R₇, R₁₀, and R₁₁ are all the same.

5. The emissive layer of claim 3 wherein of R₂, R₃, R₆, R₇, R₁₀, and R₁₁ are selected from phenyl, naphthyl and biphenyl.

6. The emissive layer of claim 4 wherein R₂, R₃, R₆, R₇, R₁₀, and R₁₁ are selected from phenyl, naphthyl and biphenyl.

7. The emissive layer of claim 1 wherein the triphenylene compound is selected from the group consisting of

8. The emissive layer of claim 1 wherein the triphenylene compound has an energy gap between its HOMO and the LUMO energy levels that is larger than the energy gap between the HOMO and the LUMO energy levels of the phosphorescent material.

9. The emissive layer of claim 1 wherein the triphenylene compound has an energy gap between its HOMO energy level and its LUMO energy level of at least about 1.8 eV.

10. The emissive layer of claim 1 wherein the triphenylene compound has a highest occupied molecular orbital that is lower than the highest occupied molecular orbital of the phosphorescent material.

11. The emissive layer of claim 1 wherein the triphenylene compound has a lowest unoccupied molecular orbital that is higher than the lowest unoccupied molecular orbital of the phosphorescent material.

12. An emissive layer comprising a phosphorescent material and a compound having a repeat unit, the repeat unit containing a triphenylene moiety, the triphenylene moiety having the formula

13. The emissive layer of claim 12 wherein the triphenylene moiety is unsubstituted.

14. The emissive layer of claim 12 wherein the compound has the formula

15. The emissive layer of claim 14 wherein the compound has the formula

16. The emissive layer of claim 12 wherein the triphenylene moiety has the structure

17. The emissive layer of claim 16 wherein the triphenylene moiety is unsubstituted.

18. The emissive layer of claim 12 wherein the compound has the structure:

19. The emissive layer of claim 18 wherein Ar is phenyl or biphenyl.

20. The emissive layer of claim 18 wherein the compound has the structure

25. The emissive layer of claim 12 wherein the triphenylene moiety has an energy gap between its HOMO and the LUMO energy levels that is larger than the energy gap between the HOMO and the LUMO energy levels of the phosphorescent material.

26. The emissive layer of claim 12 wherein the triphenylene moiety has an energy gap between its HOMO energy level and its LUMO energy level of at least about 1.8 eV.

27. The emissive layer of claim 12 wherein the triphenylene moiety has a highest occupied molecular orbital that is lower than the highest occupied molecular orbital of the phosphorescent material.

28. The emissive layer of claim 12 wherein the triphenylene moiety has a lowest unoccupied molecular orbital that is higher than the lowest unoccupied molecular orbital of the phosphorescent material.

21. An emissive layer comprising a phosphorescent material and a triphenylene compound having a benzotriphenylenylene structure.

22. The emissive layer of claim 21 wherein the aromatic triphenylene compound has the structure

29. The emissive layer of claim 21 wherein the triphenylene moiety has an energy gap between its HOMO and the LUMO energy levels that is larger than the energy gap between the HOMO and the LUMO energy levels of the phosphorescent material.

30. The emissive layer of claim 21 wherein the triphenylene compound has an energy gap between its HOMO energy level and its LUMO energy level of at least about 1.8 eV.

31. The emissive layer of claim 21 wherein the triphenylene compound has a highest occupied molecular orbital that is lower than the highest occupied molecular orbital of the phosphorescent material.

32. The emissive layer of claim 21 wherein the triphenylene compound has a lowest unoccupied molecular orbital that is higher than the lowest unoccupied molecular orbital of the phosphorescent material.

23. An emissive layer comprising a phosphorescent material and a triphenylene compound having a fused-triphenylenylene structure.

24. The emissive layer of claim 23 wherein the triphenylene compound has the structure

33. The emissive layer of claim 23 wherein the triphenylene compound has an energy gap between its HOMO and the LUMO energy levels that is larger than the energy gap between the HOMO and the LUMO energy levels of the phosphorescent material.

34. The emissive layer of claim 23 wherein the triphenylene compound has an energy gap between its HOMO energy level and its LUMO energy level of at least about 1.8 eV.

35. The emissive layer of claim 23 wherein the triphenylene compound has a highest occupied molecular orbital that is lower than the highest occupied molecular orbital of the phosphorescent material.

36. The emissive layer of claim 23 wherein the triphenylene compound has a lowest unoccupied molecular orbital that is higher than the lowest unoccupied molecular orbital of the phosphorescent material.

37. An organic electroluminescent device comprising:

an anode

a cathode

an emissive layer between the anode and the cathode, the emissive layer comprising a triphenylene compound and a phosphorescent material, the triphenylene compound having the formula

where R₁-R₃ are each independently H or a substituent selected from the group consisting of, aryl, substituted aryl, heteroaryl, substituted heteroaryl, alkyl, arylkyl, heteroalkyl, alkenyl, and alkynyl.

38. An organic electroluminescent device comprising:

an anode

a cathode

an emissive layer between the anode and the cathode, emissive layer comprising a phosphorescent material and a compound having a repeat unit, the repeat unit containing a triphenylene moiety having the formula

wherein

R₁, R₂, and R₃ is each independently selected from the group consisting H, aryl, substituted aryl, heteroaryl, substituted heteroaryl, alkyl, arylkyl, heteroalkyl, alkenyl, and alkynyl.

39. A compound having the structure