Substituted oligoazacarbazoles for light emitting diodes

• US 8,580,399 B2
• Filed: 04/08/2011
• Issued: 11/12/2013
• Est. Priority Date: 04/08/2011
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Dyatkin, Alexey, Zeng, Lichang
• Primary Examiner(s): CLARK, GREGORY D
• Application Number:
  US13/082,914
• Publication Number:
  US 20120256169A1
• Time in Patent Office: 949 Days
• Field of Search: 428/690, 428/917, 313/504, 313/505, 313/506, 257/40, 257/E51.032, 257/E51.05, 257/E51.026, 546/18, 546/79, 546/81, 546/101, 548/440
• US Class Current: 428/690
• CPC Class Codes: C07D 471/04 Ortho-condensed systems
• CPC Class Codes: C07D 519/00 Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/16 Electron transporting layers
• CPC Class Codes: H10K 50/18 Carrier blocking layers
• 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

Novel compounds containing substituted oligoazacarbazole chains are provided. These compounds are useful in organic light emitting devices, in particular as hosts in the emissive layer of such devices.

Claims

1. A compound of formula I:

Y—

X—

Z, 

 

Formula I,

wherein Y is selected from the group consisting of;

2. The compound of claim 1, wherein X is

3. The compound of claim 1, wherein A, B, C, and D are connected to each other through a bond between a carbon at the 3 or 6-position and a nitrogen at the 9-position.

4. The compound of claim 1, wherein Z is 2-dibenzothiophenyl, 4-dibenzothiophenyl, 2-dibenzofuranyl, or 4-dibenzofuranyl.

5. The compound of claim 1, wherein A, B, C, and D are not carbazole.

6. The compound of claim 1, wherein R₁, R₂, R₃, R₄, R₅, R₆, R₇, and R₈, if present, are independently selected from the group consisting of phenyl, biphenyl, triphenyl, terphenyl, naphthalene, phenalene, phenanthrene, fluorene, chrysene, dibenzothiophene, dibenzofuran, benzofuran, benzothiophene, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, indole, azaindole, benzimidazole, indazole, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine and thienodipyridine.

7. The compound of claim 1, wherein A, B, C, and D are independently selected from the group consisting of:

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

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

an anode;

a cathode; and

a first organic layer disposed between the anode and the cathode, comprising a compound having the formula I;

Y—

X—

Z 

 

Formula I,

wherein Y is selected from the group consisting of;

10. The first device of claim 9, wherein the first organic layer is an emissive layer and the compound of formula I is a host.

11. The first device of claim 10, wherein the organic layer further comprises an emissive compound.

12. The first device of claim 11, wherein the emissive compound is a transition metal complex having at least one ligand selected from the group consisting of:

13. The first device of claim 9, wherein the device further comprises a second organic layer that is a non-emissive layer and the compound having formula I is a material in the second organic layer.

14. The first device of claim 13, wherein the second organic layer is an electron transporting layer and the compound having the formula I is an electron transporting material in the second organic layer.

15. The first device of claim 13, wherein the second organic layer is a blocking layer and the compound having the formula I is a blocking material in the second organic layer.

16. The first device of claim 9, wherein the device is an organic light emitting device.

17. The first device of claim 9, wherein the device is a consumer product.