Organic light emitting diode materials

• US 9,761,807 B2
• Filed: 02/06/2014
• Issued: 09/12/2017
• Est. Priority Date: 07/15/2013
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Ma, Bin, Yeager, Walter, Barron, Edward, Cheon, Kwang-Ohk, Zeng, Lichang, Xia, Chuanjun
• Primary Examiner(s): Clark, Gregory
• Application Number:
  US14/174,396
• Publication Number:
  US 20150014649A1
• Time in Patent Office: 1,314 Days
• Field of Search: None
• CPC Class Codes: C07D 405/10 linked by a carbon chain containing aromatic rings
• CPC Class Codes: C07D 409/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 409/10 linked by a carbon chain containing aromatic rings
• CPC Class Codes: C07D 409/14 containing three or more hetero rings
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/324 comprising aluminium, e.g. Alq3
• CPC Class Codes: H10K 85/342 comprising iridium
• CPC Class Codes: H10K 85/622 containing four rings, e.g. pyrene
• 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

Abstract

The present invention relates to novel organic compounds containing a triphenylene and a carbazole. The compounds are useful for organic light-emitting diodes. The compounds are also useful for charge-transport and charge-blocking layers, and as hosts in the light-emissive layer for organic light emitting devices (OLEDs).

Claims

1. A compound having formula I:

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

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

4. The compound of claim 1, wherein G is connected to L² at the nitrogen atom of the 9-position of carbazole.

5. The compound of claim 1, wherein G is connected to L² at a carbon atom at the 1-, 2-, 3-, or 4-position of carbazole.

6. The compound of claim 1, wherein one of R^4b, R^5a, or R^5c is L²-G.

7. The compound of claim 1, wherein L² is selected from the group consisting of a direct bond, a phenyl group, and a biphenyl group.

8. The compound of claim 1, wherein R^1a, R^1b, R^1c, R^1d, R^2a, R^2b, R^2c, and R^2d are each independently selected from the group consisting of hydrogen, deuterium, aryl, heteroaryl, and combinations thereof, wherein R^3a, R^3b, R^3c, and R^3d that are not formula II are each independently selected from the group consisting of hydrogen, deuterium, aryl, heteroaryl, and combinations thereof, and wherein R^4a, R^4b, R^4c, R^5a, R^5b, R^5c, and R^5d that are not formula III are each independently selected from the group consisting of hydrogen, deuterium, aryl, heteroaryl, and combinations thereof.

9. The compound of claim 1, wherein R^1a, R^1b, R^1c, R^1d, R^2a, R^2b, R^2c, and R^2d are each independently selected from the group consisting of hydrogen, deuterium, phenyl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, pyridine, phenyl pyridine, pyridyl phenyl, triphenylene, carbazole, fluorene, dibenzofuran, dibenzothiophene, dibenzoselenophene, and combinations thereof, wherein R^3a, R^3b, R^3c, and R^3d that are not formula II are each independently selected from the group consisting of hydrogen, deuterium, phenyl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, pyridine, phenyl pyridine, pyridyl phenyl, triphenylene, carbazole, fluorene, dibenzofuran, dibenzothiophene, dibenzoselenophene, and combinations thereof, and wherein R^4a, R^4b, R^4c, R^5a, R^5b, R^5c, and R^5d that are not formula III are each independently selected from the group consisting of hydrogen, deuterium, phenyl, biphenyl, terphenyl, tetraphenyl, pentaphenyl, pyridine, phenyl pyridine, pyridyl phenyl, triphenylene, carbazole, fluorene, dibenzofuran, dibenzothiophene, dibenzoselenophene, and combinations thereof.

10. The compound of claim 1, wherein R^1a, R^1b, R^1c, R^1d, R^2a, R^2b, R^2c, and R^2d are hydrogen, wherein R^3a, R^3b, R^3c, and R^3d that are not formula II are hydrogen, and wherein R^4a, R^4b, R^4c, R^5a, R^5b, R^5c, and R^5d that are not formula III are hydrogen.

11. The compound of claim 1, wherein X is O.

12. The compound of claim 1, wherein X is S.

13. The compound of claim 1, wherein X is S, L² is a direct bond, and R^5ais L²-G.

14. The compound of claim 1, wherein X is S, L² is phenyl, and R^5ais L²-G.

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

16. A first device comprising an organic light emitting device, the organic light emitting device comprising:

an anode;

a cathode;

an organic layer, disposed between the anode and the cathode, wherein the organic layer comprises a compound having formula I;

17. The first device of claim 16, further comprising a blocking layer and the compound of formula I is a blocking material in the organic layer.

18. A formulation comprising a compound having formula I: