Organic electroluminescent materials and devices

• US 9,537,106 B2
• Filed: 05/09/2013
• Issued: 01/03/2017
• Est. Priority Date: 05/09/2013
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Kwong, Raymond, Lam, Sui Tung, Lee, Chi Hang
• Primary Examiner(s): CLARK, GREGORY D
• Application Number:
  US13/890,437
• Publication Number:
  US 20140332758A1
• Time in Patent Office: 1,335 Days
• Field of Search: None
• US Class Current: 1/1
• CPC Class Codes: C07D 471/14 Ortho-condensed systems
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/636 comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: H10K 85/6572 comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole

Abstract

Donor-acceptor compounds with nitrogen containing polyaromatics as the acceptor with emission originated from the charge transfer (CT) state is disclosed. The donor-acceptor compound is provided that has the structure of Formula 1 shown below:

wherein X₁ to X₁₂ is independently selected from the group consisting of C—R and N, wherein at least one of X₁ to X₁₂ is N, wherein each R is independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and at least one of the R comprises a donor group with at least two electron-donating nitrogens.

Claims

1. A compound having the formula:

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

3. The compound of claim 2, wherein Donor is selected from the group consisting of:

4. The compound of claim 2, wherein L is one of

5. The compound of claim 4, wherein the compound is one of

6. The compound of claim 5, wherein S₁ to S₆ and A₁-A₂ are H.

25. A formulation comprising a compound according to claim 1.

7. A first device comprising a first organic light emitting device,

further comprising:

an anode;

a cathode; and

an organic emissive layer, disposed between the anode and the cathode;

wherein the organic emissive layer comprises a first emitting compound having a structure according to Formula 1

8. The first device of claim 7, wherein the first emitting compound is selected from the group consisting of

9. The first device of claim 8, wherein Donor is selected from the group consisting of:

10. The first device of claim 9, wherein L is one of

11. The first device of claim 10, wherein the first emitting compound is one of

13. The first device of claim 7, wherein the first device emits a luminescent radiation at room temperature when a voltage is applied across the organic light emitting device;

wherein the luminescent radiation comprises a delayed fluorescence process.

14. The first device of claim 7, wherein the emissive layer further comprises a first phosphorescent emitting material.

15. The first device of claim 14, wherein the emissive layer further comprises a second phosphorescent emitting material.

16. The first device of claim 7, wherein the emissive layer further comprises a host material.

17. The first device of claim 14, wherein the first device emits a white light at room temperature when a voltage is applied across the organic light emitting device.

18. The first device of claim 17, wherein the first emitting compound emits a blue light with a peak wavelength of about 400 nm to about 500 nm.

19. The first device of claim 17, wherein the first emitting compound emits a yellow light with a peak wavelength of about 530 nm to about 580 nm.

20. The first device of claim 7, wherein the first device comprises a second organic light emitting device;

wherein the second organic light emitting device is stacked on the first organic light emitting device.

21. The first device of claim 7, wherein the first device is a consumer product.

22. The first device of claim 7, wherein the first device is an organic light-emitting device.

23. The first device of claim 7, wherein the first device is a lighting panel.

24. The first device of claim 7, wherein at least one of the R comprises a donor group with at least two electron-donating nitrogens.

12. The first device of 11, wherein S₁ to S₆ and A₁-A₂ are H.