Organic electroluminescent materials and devices

• US 9,647,218 B2
• Filed: 08/20/2014
• Issued: 05/09/2017
• Est. Priority Date: 11/14/2013
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Kwong, Raymond, Lam, Siu Tung, Lee, Chi Hang
• Primary Examiner(s): CLARK, GREGORY D
• Application Number:
  US14/464,430
• Publication Number:
  US 20150129849A1
• Time in Patent Office: 993 Days
• Field of Search: None
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/631 Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
• CPC Class Codes: H10K 85/6572 comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
• CPC Class Codes: H10K 85/6576 comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene

Abstract

A compound having the structure of Formula 1,

as well as, a first device and a formulation including the same are disclosed. In the structure of Formula 1:

• • R⁵ is

and

• • (a) at least one of R¹-R⁴ is

or (b) R¹ is

In addition, R¹, R², R³, R⁴, A¹, A², A³, A⁴, A⁵, A⁶, A⁷, A⁸, A⁹, A¹⁰, B¹, B², B³, B⁴, B⁵, B⁶, B⁷, B⁸, B⁹, B¹⁰, Y¹, Y², Y³, Y⁴, Y⁵, Y⁶, Y⁷, Y⁸, Z¹, Z², Z³, Z⁴, Z⁵, Z⁶, Z⁷, and Z⁸, are each independently selected from a variety of substituents, where adjacent A, B, Y, and Z groups are, optionally, joined to form a fused ring structure. Finally, X includes an acceptor group selected from —C_mF_2m+1, —Si_mF_2m+1, —NCO, —NCS, —OCN, —SCN, —OC_mF_2m+1, and —SC_mF_2m+1.

Claims

1. A compound comprising a structure according to Formula 1:

2. The compound of claim 1, wherein R⁵ is

3. The compound according to claim 2, wherein at least two of R¹-R⁴ are

4. The compound of claim 2, wherein at least one of R¹-R⁴ comprises an acceptor group selected from the group consisting of —

C_mF_2m+1, —

Si_mF_2m+1, —

NCO, —

NCS, —

OCN, —

SCN, —

OC_mF_2m+1, and —

SC_mF_2m+1.

5. The compound of claim 2, wherein at least one of R¹-R⁴ is an electron withdrawing group with a Hammett value (σ

_para) of at least 0.05.

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

7. The compound of claim 1, wherein R⁵ is

8. The compound of claim 7, wherein A⁵ and A⁶ are joined by a single bond.

9. The compound of claim 7, wherein A⁵ and A⁶ are joined by a single bond;

and wherein B⁵ and B⁶ are joined by a single bond.

10. The compound of claim 7, wherein at least one of R²-R⁴ is

11. The compound of claim 7, wherein at least one of R²-R⁴ comprises an acceptor group selected from the group consisting of —

C_mF_2m+1, —

Si_mF_2m+1, —

NCO, —

NCS, —

OCN, —

SCN, —

OC_mF_2m+1, and —

SC_mF_2m+1.

12. The compound of claim 7 wherein at least one R¹-R⁴ is an electron withdrawing group with a Hammett value (σ

_para) of at least 0.05.

13. The compound of claim 7, wherein the compound is selected from the group consisting of:

14. A first device comprising a first organic light emitting device, the first organic light emitting device comprising:

an anode;

a cathode; and

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

wherein the emissive layer comprises a host material doped with a first emitting compound comprising a structure according to Formula 2;

15. The first device of claim 14, wherein at least two R groups comprise a donor group with at least one electron-donating nitrogen.

16. The first device of claim 14, wherein at least two R groups comprise an acceptor group selected from the group consisting of —

F, —

C_mF_2m+1, —

Si_mF_2m+1, —

NCO, —

NCS, —

OCN, —

SCN, —

OC_mF_2m+1, and —

SC_mF_2m+1.

17. The first device of claim 14, wherein n=1,

wherein at least two of X¹ to X⁶ are CR, and

wherein at least two R groups are independently selected from the group consisting of F, C_mF_2m+1, Si_mF_2m+1, NCO, NCS, OCN, SCN, OC_mF_2m+1 and SC_mF_2m+1.

18. The first device of claim 14, wherein n=1,

wherein at least two of X¹ to X⁶ are CR,

wherein at least one R group is selected from the group consisting of —

F, —

C_mF_2m+1, —

Si_mF_2m+1, —

NCO, —

NCS, —

OCN, —

SCN, —

OC_mF_2m+1, and —

SC_mF_2m+1, and

wherein at least one R is an electron withdrawing group with a Hammett value (σ

_para) of at least 0.05.

19. The first device of claim 14, wherein the compound comprises a structure according to Formula 1:

20. The first device of claim 14, wherein the compound comprises a structure according to Formula 1:

21. The first device of claim 14, wherein the compound is selected from the group consisting of:

22. The first device of claim 14, wherein the compound comprises two structures according to Formula 2 bonded together.

23. A first device of claim 14, wherein at least one R group comprises the structure of Formula 3:

24. The first device of claim 14, wherein the first device emits a luminescent radiation at room temperature when a voltage is applied across the organic light emitting device, and wherein the luminescent radiation comprises a delayed fluorescence process.

25. A formulation comprising a compound comprising a structure according to Formula 1: