Electron transporting compounds

• US 8,415,031 B2
• Filed: 01/24/2011
• Issued: 04/09/2013
• Est. Priority Date: 01/24/2011
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Xia, Chuanjun, Mohan, Siddharth Harikrishna, Adamovich, Vadim
• Primary Examiner(s): Chriss, Jennifer A
• Assistant Examiner(s): CLARK, GREGORY D
• Application Number:
  US13/012,425
• Publication Number:
  US 20120187381A1
• Time in Patent Office: 806 Days
• Field of Search: 428/690, 428/917, 313/504, 313/505, 313/506, 548/440, 546/79, 546/81
• US Class Current: 428/690
• CPC Class Codes: C07D 491/04 Ortho-condensed systems
• CPC Class Codes: C07D 495/04 Ortho-condensed systems
• CPC Class Codes: C07D 517/04 Ortho-condensed systems
• CPC Class Codes: H10K 50/16 Electron transporting layers
• CPC Class Codes: H10K 85/626 containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene

Abstract

Compounds comprising an aza-dibenzo moiety and a condensed aromatic moiety having at least three benzene rings are provided. In particular, the compounds may comprise an azadibenzofuran, azadibenzothiophene, or azadibenzoselenophene joined directly or indirectly to an anthracene. The compounds may be used in the electron transport layer of organic light emitting devices to provide devices with improved properties.

Claims

1. A compound having the formula Ar(LiDi)n, wherein Ar contains a condensed aromatic ring system having at least three benzene rings and the condensed aromatic ring has a triplet energy lower than 440 nm;

wherein Ar is unsubstituted or substituted with one or more groups selected from the group consisting of hydrogen, deuterium, alkyl, alkoxy, amino, silyl, cyano, halogen, and aryl;

wherein L is a single bond or a bivalent linking group;

wherein n is at least 1;

wherein i is an indexing variable that identifies n structures for L_i and D_i that may be the same or different for different values of i;

wherein each L_i is independently a single bond or a bivalent linking group;

wherein each D_i independently has the structure;

2. The compound of claim 1, wherein the compound has the formula:

3. The compound of claim 1, wherein the compound has a formula selected from the group consisting of:

4. The compound of claim 1, wherein each D_i is independently selected from the group consisting of:

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

6. The compound of claim 1, wherein each L_i is independently selected from the group consisting of:

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

8. The compound of claim 1, wherein n is 1.

9. The compound of claim 1, wherein n is greater than 1 and each D_i has the same structure.

10. The compound of claim 1, wherein n is greater than 1 and at least two D_i have different structures.

11. The compound of claim 1, wherein n is 2.

12. The compound of claim 1, wherein the compound has the formula:

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

14. A first device comprising an organic light emitting device, comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, further comprising a compound having the formula Ar(LiDi)n,

wherein Ar contains a condensed aromatic ring system having at least three benzene rings and the condensed aromatic ring has a triplet energy lower than 440 nm;

wherein Ar is unsubstituted or substituted with one or more groups selected from the group consisting of hydrogen, deuterium, alkyl, alkoxy, amino, silyl, cyano, halogen, and aryl;

wherein L is a single bond or a divalent linking group;

wherein n is a least 1;

wherein i is an indexing variable that identifies n structures for L_i and D_i that may be the same or different for different values of i;

wherein each L_i is independently a single bond or a bivalent linking group;

wherein each D_i independently has the structure;

15. The first device of claim 14, wherein the compound has the formula:

16. The first device of claim 14, wherein the compound has a formula selected from the group consisting of:

17. The first device of claim 14, wherein each D_i is independently selected from the group consisting of:

18. The first device of claim 14, wherein each L_i is selected from the group consisting of:

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

20. The device of claim 14, wherein the compound has the formula:

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 organic layer is a non-emissive layer and the compound is a non-emissive compound.

23. The first device of claim 22, wherein the organic layer is an electron transport layer and the compound is an electron transport material.

24. The first device of claim 23, wherein the electron transport layer is doped with an n-type conductivity dopant.

25. The first device of claim 24, wherein the n-type conductivity dopant is a compound containing Li, Na, K, Rb, or Cs.

26. The first device of claim 25, wherein the n-type conductivity dopant is selected from the group consisting of LiF, CsF, NaCl, KBr, and LiQ.

27. The first device of claim 14, wherein the organic layer further comprises an emissive compound that is a transition metal complex having at least one ligand selected from the group consisting of:

28. The first device of claim 14, wherein the first device is a consumer product.

29. The first device of claim 14, wherein the first device is an organic light emitting device.