Organic electroluminescent materials and devices

• US 9,634,265 B2
• Filed: 08/06/2013
• Issued: 04/25/2017
• Est. Priority Date: 04/28/2009
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Xia, Chuanjun, Fiordeliso, James, Kwong, Raymond
• Primary Examiner(s): Yamnitzky, Marie R.
• Application Number:
  US13/960,264
• Publication Number:
  US 20130320318A1
• Time in Patent Office: 1,358 Days
• Field of Search: None
• CPC Class Codes: C07F 15/0033 Iridium compounds
• CPC Class Codes: C07F 15/0086 Platinum compounds
• CPC Class Codes: C09K 11/025 non-luminescent particle coatings or suspension media
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1007 Non-condensed systems
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• 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
• CPC Class Codes: H10K 85/346 comprising platinum
• CPC Class Codes: H10K 85/622 containing four rings, e.g. pyrene
• CPC Class Codes: H10K 85/6576 comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
• CPC Class Codes: Y02E 10/549 Organic PV cells

Abstract

Novel organic compounds comprising ligands with deuterium substitution are provided. In particular, the compound is an iridium complex comprising methyl-d₃ substituted ligands. The compounds may be used in organic light emitting devices to provide devices having improved color, efficiency and lifetime.

Claims

1. A compound comprising a ligand having the structure:

2. The compound of claim 1, wherein at least one of the substituents of R_A and R_B is CD₃ attached directly to ring A, ring B, or a ring that is conjugated or fused to ring A or ring B.

3. The compound of claim 1, wherein X_A and X_B are independently C or N and when X_A is N, R₁ is aryl.

4. The compound of claim 1, wherein X_A and X_B are independently C or N and when X_A is N, R₁ is phenyl further substituted with a group consisting of alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, aryl, and heteroaryl and wherein the group includes at least one of CD, CD₂ or CD₃.

5. The compound of claim 1, wherein the ligand is selected from the group consisting of:

6. The compound of claim 5, wherein the ligand has the formula:

7. The compound of claim 5, wherein the ligand has the formula:

8. The compound of claim 5, wherein the ligand has the formula:

9. The compound of claim 1, wherein A is selected from the group consisting of pyridine, pyridazine, pyrimidine, pyrazine, and triazine.

10. The compound of claim 1, wherein B is selected from the group consisting of benzene, pyridine.

11. The compound of claim 1, wherein the ligand having FORMULA I is a ligand in a homoleptic compound.

12. The compound of claim 1, wherein the ligand having FORMULA I is a ligand in a heteroleptic compound.

13. 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 compound further comprising a ligand having the structure;

14. The device of claim 13, wherein the ligand has the structure:

15. The device of claim 14, wherein at least one of R_A, R_B, R₁ and R₂ is CD₃.

16. The device of claim 13, wherein at least one of the substituents of R_A and R_B is CD₃ attached directly to ring A, ring B, or a ring that is conjugated or fused to ring A or ring B.

17. The device of claim 13, wherein X_A and X_B are independently C or N and when X_A is N, R₁ is aryl.

18. The device of claim 13, wherein X_A and X_B are independently C or N and when X_A is N, R₁ is phenyl further substituted with a group consisting of alkyl, alkoxy, amino, alkenyl, alkynyl, arylalkyl, aryl, and heteroaryl and wherein the group includes at least one of CD, CD₂ or CD₃.

19. The device of claim 13, wherein the ligand is selected from the group consisting of:

20. The device of claim 13, wherein A is selected from the group consisting of imidazole, pyridine, pyridazine, pyrimidine, pyrazine, and triazine.

21. The device of claim 13, wherein B is selected from the group consisting of benzene, pyridine.

22. The device of claim 13, wherein the organic layer is an emissive layer and the compound is an emitting dopant.

23. The device of claim 22, wherein the organic layer further comprises a host.

24. The device of claim 23, wherein the host has the formula:

25. The device of claim 23, wherein the host is

26. A consumer product comprising a device, the device comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, wherein the organic layer comprises a compound comprising a ligand having the structure;