Host compounds for red phosphorescent OLEDs

• US 9,118,017 B2
• Filed: 12/18/2012
• Issued: 08/25/2015
• Est. Priority Date: 02/27/2012
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Xia, Chuanjun, Cheon, Kwang-Ohk
• Primary Examiner(s): CLARK, GREGORY D
• Application Number:
  US13/718,248
• Publication Number:
  US 20130221332A1
• Time in Patent Office: 980 Days
• Field of Search: None
• US Class Current: 1/1
• CPC Class Codes: H10K 2101/10 Triplet emission
• 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 85/111 comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
• CPC Class Codes: H10K 85/324 comprising aluminium, e.g. Alq3
• CPC Class Codes: H10K 85/342 comprising iridium
• CPC Class Codes: H10K 85/622 containing four rings, e.g. pyrene
• CPC Class Codes: H10K 85/626 containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene

Abstract

Novel compounds containing a triphenylene moiety linked to an αβ connected binaphthyl ring system are provided. These compounds have surprisingly good solubility in organic solvents and are useful as host compounds in red phosphorescent OLEDs.

Claims

1. A compound having the formula:

2. The compound of claim 1, wherein L is aryl.

3. The compound of claim 2, wherein L is unsubstituted aryl.

4. The compound of claim 3, wherein L is phenyl.

5. The compound of claim 1, wherein L is a single bond.

6. The compound of claim 1, wherein L is a nitrogen-, an oxygen-, a selenium-, or a sulfur-containing heteroaryl group.

7. The compound of claim 6, wherein L contains a group having the formula:

8. The compound of claim 6, wherein L contains one or more groups selected from the group consisting of:

9. The compound of claim 1, wherein R₁, R₂, and R₃ are selected from the group consisting of hydrogen, deuterium, aryl, heteroaryl, and combinations thereof.

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

26. The compound of claim 1, wherein:

(i) R₁ is independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

(ii) R₃ is independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

or

(iii) each R₁ and R₃ is independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

10. A compound having the formula:

12. A first device comprising an organic light emitting device, further comprising:

an anode;

a cathode; and

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

13. The first device of claim 12, wherein the organic layer is an emissive layer and the compound of Formula I is a host.

14. The first device of claim 13, further comprising a first dopant material that is an emissive dopant comprising a transition metal complex having at least one ligand or part of the ligand if the ligand is more than bidentate selected from the group consisting of:

15. The first device of claim 14, wherein the transition metal complex having at least one ligand or part of the ligand if the ligand is more than bidentate selected from the group consisting of:

16. The first device of claim 14, further comprising a second dopant material.

17. The first device of claim 16, wherein the second dopant material comprises a metal complex.

18. The first device of claim 12, wherein the emissive dopant is a phosphorescent emitter having a peak wavelength of between about 580 nanometers to about 700 nanometers.

19. The first device of claim 12, wherein the organic layer is deposited using a solution process.

20. The first device of claim 12, wherein the organic layer is a non-emissive layer.

21. The first device of claim 12, wherein the organic layer is a first organic layer, and the device further comprises a second organic layer that is a non-emissive layer and the compound having Formula I is a material in the second organic layer.

22. The first device of claim 12, wherein the second organic layer is a blocking layer comprising the compound having the Formula I.

23. The first device of claim 12, wherein the first device is a consumer product.

24. The first device of claim 12, wherein the first device is an organic light-emitting device.

25. The first device of claim 12, wherein the first device comprises a lighting panel.