Organic electroluminescent materials and devices

• US 9,287,513 B2
• Filed: 03/06/2013
• Issued: 03/15/2016
• Est. Priority Date: 09/24/2012
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Xia, Chuanjun, Lin, Chun
• Primary Examiner(s): Chriss, Jennifer
• Assistant Examiner(s): Kershner, Dylan
• Application Number:
  US13/786,519
• Publication Number:
  US 20140084260A1
• Time in Patent Office: 1,105 Days
• Field of Search: None
• US Class Current: 1/1
• CPC Class Codes: C07F 5/02 Boron compounds
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1007 Non-condensed systems
• CPC Class Codes: C09K 2211/1011 Condensed systems
• CPC Class Codes: C09K 2211/1044 containing two nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/1055 with other heteroatoms
• CPC Class Codes: C09K 2211/1096 containing other heteroatoms
• CPC Class Codes: H05B 33/10 Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/322 comprising boron
• CPC Class Codes: H10K 85/656 comprising two or more different heteroatoms per ring H10K85/652 takes precedence
• CPC Class Codes: H10K 85/657 Polycyclic condensed heteroaromatic hydrocarbons
• 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
• CPC Class Codes: H10K 85/658 Organoboranes

Abstract

In certain embodiments, the invention provides boron-nitrogen heterocycles having Formula (I):

wherein one of the E₁ and E₂ is N, and one of the E₁ and E₂ is B; wherein E₃ and E₄ is carbon; wherein ring Y and ring Z are 5-membered or 6-membered carbocyclic or heterocyclic aromatic ring fused to ring X; wherein R₂ and R₃ represent mono, di, tri, tetra substitutions or no substitution; wherein R₂ and R₃ are each independently selected from various substituents; and wherein any two adjacent R₂, and R₃ are optionally joined to form a ring, which may be further substituted. In certain embodiments, the invention provides devices, such as organic light emitting devices, that comprise such boron-nitrogen heterocycles.

Claims

1. A compound having the Formula (I):

2. The compound of claim 1, wherein E₁ is B, and E₂ is N.

3. The compound of claim 1, wherein E₁ is N, and E₂ is B.

4. The compound of claim 1, wherein ring Y is

5. The compound of claim 1, wherein ring Z is selected from the group consisting of:

6. The compound of claim 1, wherein ring Z is

7. The compound of claim 1, wherein R₁, R₂, and R₃ are independently selected from the group consisting of phenyl, pyridine, triazine, pyrimidine, phenanthrene, naphthalene, anthracene, triphenylene, pyrene, chrysene, fluoranthene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, aza-carbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene, each of which may be further substituted.

8. The compound of claim 1, wherein the compound has the formula

9. The compound of claim 1, wherein the compound is a compound having Formula (II):

10. The compound of claim 9, wherein G is phenylene, pyridine, biphenylene, triazine, pyrimidine, triphenylene, naphthylene, anthracene, chrysene, pyrene, fluoranthene, phenanthrene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, aza-carbazole, aza-dibenzothiphene, aza-dibenzofuran, aza-debenzoselenophene, or combinations thereof.

11. The compound of claim 10, which is

12. The compound of claim 1, wherein the compound is a compound having Formula (III):

13. The compound of claim 12, wherein G¹, G², and G³ independently are phenylene, pyridine, biphenylene, triazine, pyrimidine, triphenylene, naphthylene, anthracene, chrysene, pyrene, fluoranthene, phenanthrene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, aza-carbazole, aza-dibenzothiphene, aza-dibenzofuran, aza-debenzoselenophene, or combinations thereof.

14. The compound of claim 13, which is:

15. The compound of claim 1, wherein, the compound is a compound having Formula (IV):

16. The compound of claim 15, wherein G⁴ is phenylene, pyridine, biphenylene, triazine, pyrimidine, triphenylene, naphthylene, anthracene, chrysene, pyrene, fluoranthene, phenanthrene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, aza-carbazole, aza-dibenzothiphene, aza-dibenzofuran, aza-debenzoselenophene, or combinations thereof.

17. The compound of claim 16, which is:

18. The compound of claim 1, wherein the compound is a compound of Formula (V)

19. The compound of claim 18, wherein R⁵¹ is phenyl, pyridyl, biphenylyl, triazinyl, pyrimidinyl, triphenylyl, naphthyl, anthracenyl, chrysene, pyrene, fluoranthene, phenanthrene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, aza-carbazole, aza-dibenzothiphene, aza-dibenzofuran, aza-debenzoselenophene, or combinations thereof.

20. The compound of claim 18, which is:

21. The compound of claim 1, wherein the compound is a compound of Formula (VI)

22. The compound of claim 21, wherein:

R⁶¹ is phenyl, pyridyl, biphenylyl, triazinyl, pyrimidinyl, triphenylyl, naphthyl, anthracenyl, chrysene, pyrene, fluoranthene, phenanthrene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, aza-carbazole, aza-dibenzothiphene, aza-dibenzofuran, aza-debenzoselenophene, or combinations thereof; and

R⁶² is phenyl, pyridyl, biphenylyl, triazinyl, pyrimidinyl, triphenylyl, naphthyl, anthracenyl, chrysene, pyrene, fluoranthene, phenanthrene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, aza-carbazole, aza-dibenzothiphene, aza-dibenzofuran, aza-debenzoselenophene, or combinations thereof.

23. The compound of claim 22, which is:

24. The compound of claim 1, wherein the compound is a compound of Formula (VII)

25. The compound of claim 24, wherein:

R⁷¹ is phenyl, pyridyl, biphenylyl, triazinyl, pyrimidinyl, triphenylyl, naphthyl, anthracenyl, chrysene, pyrene, fluoranthene, phenanthrene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, aza-carbazole, aza-dibenzothiphene, aza-dibenzofuran, aza-debenzoselenophene, or combinations thereof; and

R⁷² is phenyl, pyridyl, biphenylyl, triazinyl, pyrimidinyl, triphenylyl, naphthyl, anthracenyl, chrysene, pyrene, fluoranthene, phenanthrene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, aza-carbazole, aza-dibenzothiphene, aza-dibenzofuran, aza-debenzoselenophene, or combinations thereof.

26. The compound of claim 25, which is:

27. The compound of claim 1, where the compound is a compound having Formula (VIII):

28. The compound of claim 27, wherein G⁵ is phenylene, pyridine, biphenylene, triazine, pyrimidine, triphenylene, naphthylene, anthracene, chrysene, pyrene, fluoranthene, phenanthrene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, aza-carbazole, aza-dibenzothiphene, aza-dibenzofuran, aza-debenzoselenophene, or combinations thereof.

29. The compound of claim 27, which is:

30. A first device comprising a first organic light emitting device, which further comprises:

an anode;

a cathode; and

an organic layer disposed between the anode and the cathode comprising a compound having the Formula (I);

31. The first device of claim 30, wherein the first device is a consumer product.

32. The first device of claim 30, wherein the first device is an organic light-emitting device.

33. The first device of claim 30, wherein the first device comprises a lighting panel.

34. The first device of claim 30, wherein the organic layer is an emissive layer and the compound of Formula (I) is an emissive dopant.

35. The first device of claim 34, where the device is a delayed fluorescence device.

36. The first device of claim 30, wherein the organic layer is an emissive layer and the compound of Formula (I) is a host.

37. The first device of claim 36, wherein the emissive layer further comprises a fluorescent emissive dopant.

38. The first device of claim 36, wherein the emissive layer further comprises an emissive dopant, which is 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:

39. The first device of claim 30, wherein the organic layer is a hole injecting layer or a hole transporting layer.

40. The first device of claim 30, wherein the organic layer is an electron injecting layer or an electron transporting layer.

41. The first device of claim 30, wherein the organic layer is an exciton blocking layer or a charge blocking layer.