Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-9735373-B2
Application number	US-201313914124-A
Country	US
Kind code	B2
Filing date	Jun 10, 2013
Priority date	Jun 10, 2013
Publication date	Aug 15, 2017
Grant date	Aug 15, 2017

Abstract

Aluminum chelate complex compounds with two substituted 8-hydroxyquinoline ligand and one dibenzothiophene, dibenzofuran or dibenzoselenophene ligands or aza-analogs of these molecules, attached directly or through an aromatic spacer to the oxygen atom is provided to improve lifetime, operating voltage and efficiency of an OLED. Additional substitution of dibenzothiophene or dibenzofuran ring may also provide charge delocalization, HOMO modification and higher Tg.

First claim

We claim:

1. A compound having a structure according to Formula I

wherein M is a group III element;
wherein L is selected from the group consisting of

and L is optionally further substituted with one or more groups selected from hydrogen, deuterium, alkyl, cycloalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, aryl, heteroaryl, and combinations thereof;
wherein A contains a group selected from the group consisting of dibenzoselenophene, aza-dibenzofuran, aza-dibenzothiophene, aza-dibenzoselenophene, and combination thereof, which are optionally further substituted with one or more groups selected from hydrogen, deuterium, alkyl, cycloalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, aryl, heteroaryl, and combinations thereof;
wherein R 3 and R 6 each represent mono, di substitutions, or no substitution;
wherein R 4 and R 5 each represent mono, di, tri substitutions, or no substitution; and
wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are each independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, aryl, heteroaryl, and combinations thereof.

2. The compound of claim 1 , wherein M is selected from the group consisting of Al, In and Ga.

3. The compound of claim 1 , wherein M is Al.

4. The compound of claim 1 , wherein L is

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

6. The compound of claim 1 , wherein R 1 and R 2 are each independently selected from the group consisting of hydrogen, deuterium, methyl, ethyl, propyl, iso-propyl, and combinations thereof.

7. The compound of claim 1 , wherein M is aluminum; and wherein R 3 , R 4 , R 5 and R 6 are hydrogen.

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

9. The compound of claim 7 , wherein A is selected from the group consisting of

10. A formulation comprising a compound of claim 1 .

11. A first device comprising a first organic light emitting device, further comprising:
an anode;
a cathode;
an organic layer, disposed between the anode and the cathode, comprising a compound having a structure according to Formula I

wherein M is a group III element;
wherein L is selected from the group consisting of

and L is optionally further substituted with one or more groups selected from hydrogen, deuterium, alkyl, cycloalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, aryl, heteroaryl, and combinations thereof;
wherein A contains a group selected from the group consisting of dibenzoselenophene, aza-dibenzofuran, aza-dibenzothiophene, aza-dibenzoselenophene, and combination thereof, which are optionally further substituted with one or more groups selected from hydrogen, deuterium, alkyl, cycloalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, aryl, heteroaryl, and combinations thereof;
wherein R 3 and R 6 each represent mono, di substitutions, or no substitution;
wherein R 4 and R 5 each represent mono, di, tri substitutions, or no substitution; and
wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are each independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, aryl, heteroaryl, and combinations thereof.

12. The first device of claim 11 , wherein M is selected from the group consisting of Al, In and Ga.

13. The first device of claim 11 , wherein M is Al.

14. The first device of claim 11 , wherein L is

15. The first device of claim 11 , wherein A is selected from the group consisting of:

16. The first device of claim 11 , wherein M in the compound is aluminum; and wherein R 3 , R 4 , R 5 and R 6 are hydrogen.

17. The first device of claim 11 , wherein the organic layer is an emissive layer and the compound having Formula I is a host.

18. The first device of claim 11 , wherein R 1 and R 2 are each independently selected from the group consisting of hydrogen, deuterium, methyl, ethyl, propyl, iso-propyl, and combinations thereof.

19. The first device of claim 17 , wherein the organic layer further comprises an emissive dopant.

20. The first device of claim 19 , wherein the emissive dopant is a transition metal complex having at least one ligand selected from the group consisting of:

wherein R a , R b , and R c may represent mono, di, tri or tetra substitutions;
R a , R b , and R e are independently selected from the group consisting of hydrogen, 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
two adjacent substituents of R a , R b , and R c are optionally joined to form a fused ring.

21. The first device of claim 11 , wherein the organic layer is a blocking layer and the compound having the Formula I is a blocking material in the organic layer.

22. The first device of claim 11 , wherein the organic layer is an electron transporting layer and the compound having the Formula I is an electron transporting material in the organic layer.

23. The first device of claim 11 , wherein the first device is a consumer product.

24. The first device of claim 11 , wherein the first device is an organic light-emitting device.

25. The first device of claim 11 , wherein the first device is a lighting panel.

Assignees

• Dyatkin Alexey
• Xia Chuanjun
• Li David Zenan
• Universal Display Corp

Inventors

• Dyatkin Alexey
• Xia Chuanjun
• Li David Zenan

Classifications

• H01L51/0085

  Electricity · mapped topic

• H01L51/0081 Primary

  Electricity · mapped topic

• C07F5/069 Primary

  without C-aluminium linkages · CPC title

• H01L51/5028

  Electricity · mapped topic

• H10K50/121

  for assisting energy transfer, e.g. sensitization · CPC title