Compounds for triplet-triplet annihilation upconversion

• US 9,196,860 B2
• Filed: 12/04/2012
• Issued: 11/24/2015
• Est. Priority Date: 12/04/2012
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Xia, Chuanjun
• Primary Examiner(s): Ho, Anthony
• Application Number:
  US13/693,122
• Publication Number:
  US 20140151646A1
• Time in Patent Office: 1,085 Days
• Field of Search: 257/40, 257/E51.001
• US Class Current: 1/1
• CPC Class Codes: C07F 15/0033 Iridium compounds
• CPC Class Codes: C07F 15/0066 without a metal-carbon linkage
• CPC Class Codes: C07F 15/0093 without a metal-carbon linkage
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/185 of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
• CPC Class Codes: H10K 50/125 specially adapted for multicolour light emission, e.g. for emitting white light
• CPC Class Codes: H10K 50/80 Constructional details
• CPC Class Codes: H10K 59/38 comprising colour filters or colour changing media [CCM]
• 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 85/346 comprising platinum
• CPC Class Codes: H10K 85/791 Starburst compounds
• CPC Class Codes: Y02E 10/549 Organic PV cells

Abstract

Novel compounds, and in particular, a dendritic system for improved triple-triplet annihilation upconversion (TTA-UC) are provided. The core of the dendrimer compound includes a metal complex, and on the peripheral, multiple acceptor moieties are covalently linked to the core through a spacer. Consequently, a high efficiency TTA-UC system in both solution and solid state is provided, with particularly high efficiency in the solid state. Additionally, organic light emitting devices (OLEDs) comprising a layer including these novel compounds are provided.

Claims

1. A compound for triplet-triplet annihilation upconversion comprising:

a metal complex sensitizer core;

a first acceptor group; and

a first spacer group between the metal complex core and the first acceptor group, wherein the first acceptor group has a first triplet energy lower than a first triplet energy of the metal complex sensitizer core;

wherein the metal complex sensitizer core and the first acceptor group are jointly capable of performing triplet-triplet annihilation upconversion of light incident on the compound.

2. The compound of claim 1, wherein the first spacer group substantially surrounds the metal complex sensitizer core.

3. The compound of claim 1, further comprising a second spacer group, wherein the second spacer group substantially surrounds the first acceptor group.

4. The compound of claim 3, further comprising a second acceptor group.

5. The compound of claim 4, wherein the second acceptor group substantially surrounds the second spacer group.

6. The compound of claim 1, further comprising a second acceptor group.

7. The compound of claim 1, further comprising a second spacer group.

8. A device comprising a layer, the layer comprising a compound of claim 1.

9. The device of claim 8, wherein the device comprises an OLED.

10. The device of claim 9, further comprising a thin film encapsulation layer disposed over or under the OLED.

11. A consumer product comprising the compound of claim 1.

12. The compound of claim 1, wherein the first acceptor group is not bonded directly to the metal complex sensitizer core.

13. The compound of claim 12, wherein the first acceptor group is covalently linked to the metal complex sensitizer core through the first spacer group.

14. A compound for triplet-triplet annihilation upconversion, wherein the compound has the following general structure:

15. The compound of claim 14, wherein ml is in the range of 1 to 20.

16. The compound of claim 14, wherein mx is in the range of 0 to 20.

17. The compound of claim 14, wherein n is in the range of 1 to 20.

18. The compound of claim 14, wherein the metal complex is selected from the group consisting of:

an iridium complex, an osmium complex, a platinum complex, a palladium complex, a rhenium complex, a ruthenium complex, and a gold complex.

19. The compound of claim 14, wherein the acceptor group B is a fused aromatic group.

20. The compound of claim 14, wherein the acceptor group B is selected from the group consisting of:

naphthalene, anthracene, tetracene, pyrene, chrysene, and perylene.

21. The compound of claim 14, wherein the ratio of the acceptor group B to the metal complex A is at least 4.

22. The compound of claim 14, wherein the spacer group Lis selected from the group consisting of:

alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, ester, and combinations thereof.

23. A device comprising a layer, the layer comprising a compound of claim 14.

24. The device of claim 23, wherein the device comprises a light emitting diode.

25. The device of claim 23, wherein the device comprises an OLED.

26. The device of claim 25, further comprising a thin film encapsulation layer disposed over or under the OLED.

27. A consumer product comprising the compound of claim 14.

28. A photovoltaic device comprising the compound of claim 14.

29. A device, comprising:

an organic light emitting device comprising an emissive material having an emissive spectrum; and

an up-conversion layer disposed adjacent to the organic light emitting device such that light emitted by the organic light emitting device is incident on the up-conversion layer, the up conversion layer comprising the compound of claim 14.

30. A compound selected from the group consisting of: