Organic electroluminescent materials and devices

• US 9,318,710 B2
• Filed: 03/07/2013
• Issued: 04/19/2016
• Est. Priority Date: 07/30/2012
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Kwong, Raymond
• Primary Examiner(s): Zucker, Paul A
• Assistant Examiner(s): LUDERER, MARK R
• Application Number:
  US13/788,741
• Publication Number:
  US 20140027734A1
• Time in Patent Office: 1,139 Days
• Field of Search: 564/11, 257/40, 546/13, 548/110, 549/4
• US Class Current: 1/1
• CPC Class Codes: C07F 5/02 Boron compounds
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/15 Hole transporting layers
• CPC Class Codes: H10K 50/16 Electron transporting layers
• CPC Class Codes: H10K 50/17 Carrier injection layers
• CPC Class Codes: H10K 50/171 Electron injection layers
• CPC Class Codes: H10K 50/18 Carrier blocking layers
• CPC Class Codes: H10K 85/322 comprising boron
• CPC Class Codes: H10K 85/615 Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
• CPC Class Codes: H10K 85/626 containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
• CPC Class Codes: H10K 85/657 Polycyclic condensed heteroaromatic hydrocarbons

Abstract

Boron-nitrogen polyaromatic compounds having a fused aromatic ring system are provided, where the compounds include a [1,2]azaborino[1,2-a][1,2]azaborine

which is optionally fused to one or more aromatic rings or fused aromatic rings; wherein the fused aromatic ring system is substituted by one or more substituents, R, that are not fused to the aromatic ring system, selected from 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 wherein any two adjacent substituents, R, are optionally joined to form one or more non-aromatic rings. Devices, such as organic light emitting devices (OLEDs) that comprise light emitting materials are also provided.

Claims

1. A compound comprising:

a fused aromatic ring system comprising a [1,2]azaborino[1,2-a][1,2]azaborine

2. The compound of claim 1, wherein said fused aromatic ring system is selected from the group consisting of:

3. The compound of claim 1, wherein R is selected from the group consisting of alkyl, cycloalkyl, amino, silyl, aryl, heteroaryl, and combinations thereof.

4. The compound of claim 1, wherein the compound is a compound of Formula (II), Formula (III), or Formula (IV):

5. The compound of claim 4, wherein each one of R₁ to R₂₂ that is not joined to an adjacent R to form a fused ring is independently selected from the group consisting of hydrogen, aryl, heteroaryl, and NR_aR_b;

and wherein R_a and R_b are aryl or heteroaryl, which can be further substituted.

6. The compound of claim 4, wherein the compound is a compound of Formula (II) and at least one of R₅, R₈, R₁₃, or R₁₆ is not hydrogen or deuterium.

7. The compound of claim 4, wherein the compound is a compound of Formula (III) or Formula (IV), and at least one of R₈, R₁₁, R₁₉, or R₂₂ is not hydrogen or deuterium.

8. The compound of claim 4, wherein the compound is a compound of Formula (II) and at least one of R₅, R₈, R₁₃, or R₁₆ is aryl, heteroaryl or NR_aR_b;

and wherein R_a and R_b are aryl or heteroaryl, which can be further substituted.

9. The compound of claim 4, wherein the compound is a compound of Formula (III) or Formula (IV) and at least one of R₈, R₁₁, R₁₉, or R₂₂ is aryl, heteroaryl or NR_aR_b;

and wherein R_a and R_b are aryl or heteroaryl, which can be further substituted.

10. The compound of claim 4, wherein the compound is a compound of Formula (II) and at least one of R₁, R₄, R₉, or R₁₂ is not hydrogen or deuterium.

11. The compound of claim 4, wherein the compound is a compound of Formula (III) or Formula (IV), and at least one of R₁, R₄, R₇, R₁₂, R₁₅ or R₁₈ is not hydrogen or deuterium.

12. The compound of claim 4, wherein the compound is a compound of Formula (II) and at least one of R₁, R₄, R₉ or R₁₂ is aryl, heteroaryl or NR_aR_b;

and wherein R_a and R_b are aryl or heteroaryl, which can be further substituted.

13. The compound of claim 4, wherein the compound is a compound of Formula (III) or Formula (IV), and at least one of R₁, R₄, R₇, R₁₂, R₁₅ or R₁₈ is aryl, heteroaryl or NR_aR_b;

and wherein R_a and R_b are aryl or heteroaryl.

14. The compound of claim 8, wherein R₅ and R₁₃ are phenyl or NR_aR_b.

15. The compound of claim 14, wherein R₅ and R₁₃ are NR_aR_b, and R_a and R_b are phenyl.

16. The compound of claim 9, wherein R₈ and R₁₉ are phenyl or NR_aR_b.

17. The compound of claim 16, wherein R₅ and R₁₃ are NR_aR_b, and R_a and R_b are phenyl.

18. The compound of claim 12, wherein R₁ and R₉ are phenyl or NR_aR_b.

19. The compound of claim 18, wherein R₅ and R₁₃ are NR_aR_b, and R_a and R_b are phenyl.

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

33. The compound of claim 1, wherein the

20. A compound, having the structure of Formula (III) or Formula (IV):

21. The compound of claim 20, wherein R₅ and R₁₃ are NR_aR_b, and R_a and R_b are phenyl.

23. A device comprising an organic light emitting device, said organic light emitting device comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, comprising a compound that comprises;

a fused aromatic ring system comprising a [1,2]azaborino[1,2-a][1,2]azaborine

24. The device of claim 23, wherein the organic layer is an emissive layer and the compound of Formula (I) is an emissive dopant.

25. The device of claim 23, wherein the organic layer is an emissive layer and the compound of Formula (I) is a host.

26. The device of claim 23, wherein the organic layer is a hole injecting layer or a hole transporting layer.

27. The device of claim 23, wherein the organic layer is an electron injecting layer or an electron transporting layer.

28. The device of claim 23, wherein the organic layer is an exciton blocking layer.

29. The device of claim 23, wherein the device is adapted for emitting delayed fluorescence.

30. The device of claim 23, wherein the device is a consumer product comprising the organic light emitting device.

31. The device of claim 23, wherein the device is an second organic light-emitting device.

32. The device of claim 23, wherein the device comprises a lighting panel.