Organic electroluminescent materials and devices

• US 9,401,482 B2
• Filed: 12/12/2014
• Issued: 07/26/2016
• Est. Priority Date: 10/08/2010
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Dyatkin, Alexey Borisovich
• Primary Examiner(s): Clark, Gregory
• Application Number:
  US14/568,929
• Publication Number:
  US 20150097176A1
• Time in Patent Office: 592 Days
• Field of Search: None
• US Class Current: 1/1
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 2102/103 comprising indium oxides, e.g. ITO
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 50/14 Carrier transporting layers
• CPC Class Codes: H10K 50/16 Electron transporting layers
• CPC Class Codes: H10K 50/18 Carrier blocking layers
• CPC Class Codes: H10K 85/324 comprising aluminium, e.g. Alq3
• CPC Class Codes: H10K 85/342 comprising iridium
• CPC Class Codes: H10K 85/633 comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
• CPC Class Codes: H10K 85/6572 comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
• CPC Class Codes: H10K 85/6574 comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
• CPC Class Codes: H10K 85/6576 comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
• CPC Class Codes: Y10S 428/917 Electroluminescent

Abstract

Compounds comprising a 3,9-linked oligocarbazole moiety and a dibenzothiophene, dibenzofuran, dibenzoselenophene, aza-dibenzothiophene, aza-dibenzofuran, or aza-dibenzoselenophene are provided. The 3,9-linked oligocarbazole and dibenzo or aza-dibenzo moiety are separated by an aromatic spacer. The compounds may be used as non-emissive materials for phosphorescent OLEDs to provide devise having improved performance.

Claims

1. A compound having the formula:

2. The compound of claim 1, wherein n is 1, 2, or 3.

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

4. The compound of claim 1, wherein A, B, C, and D are

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

7. The compound of claim 1, wherein X is selected from the group consisting of terphenyl.

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

6. A compound, having the formula:

8. 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;

9. The first device of claim 8, wherein n is 1, 2, or 3.

10. The first device of claim 8, wherein A, B, C, and D are

11. The first device of claim 8, wherein Y is 2-dibenzothiophenyl, 4-dibenzothiophenyl, 2-dibenzofuranyl, or 4-dibenzofuranyl.

12. The first device of claim 8, wherein the first organic layer is an emissive layer and the compound having

13. The first device of claim 10, wherein the first organic layer further comprises an emissive dopant having the formula

14. The first device of claim 13, wherein the emissive dopant is selected from the group consisting of:

15. The first device of claim 8, 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.

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

17. The first device of claim 8, wherein the first organic layer is disposed using solution processing.

18. The first device of claim 8, wherein the device is at least one of an organic light emitting device and a consumer product.

19. The first device of claim 8, wherein the compound is selected from the group consisting of: