Compound

Patent metadata

Field	Value
Publication number	US-11856845-B2
Application number	US-201816955756-A
Country	US
Kind code	B2
Filing date	Dec 20, 2018
Priority date	Dec 21, 2017
Publication date	Dec 26, 2023
Grant date	Dec 26, 2023

Abstract

Compound A compound of formula (I): (I) wherein R 1 and R 2 are each independently a linear, branched or cyclic C 1-20 alkyl group; and Ar 1 and Ar 2 are each independently an aromatic or heteroaromatic group which is unsubstituted or substituted with one or more substituents. The compound may be used in n-doping of an organic semiconductor. Such an n-doped organic semiconductor may be used in an organic electronic device, for example an electron injection layer of an organic light-emitting device.

First claim

The invention claimed is:

1. A compound of formula (I):

wherein R 1 and R 2 are each independently a linear, branched or cyclic C 1-20 alkyl group; and
Ar 1 and Ar 2 are each independently an aromatic or heteroaromatic group which is unsubstituted or substituted with one or more substituents.

2. A compound according to claim 1 wherein Ar 1 is a C 6-20 aromatic group.

3. A compound according to claim 2 wherein Ar 1 is phenyl.

4. A compound according to claim 1 wherein Ar 2 is a C 6-20 aromatic group.

5. A compound according to claim 4 wherein Ar 2 is phenyl.

6. A compound according to claim 1 wherein Ar 1 and Ar 2 are each independently unsubstituted or substituted with one or more substituents selected from the group consisting of:
branched, linear or cyclic C 1-12 alkyl wherein one or more non-adjacent, non-terminal C atoms of the C 1-12 alkyl group may be replaced with O, S, NR 5 , C═O or COO wherein R 5 is a C 1-12 hydrocarbyl group; and ionic substituents.

7. A composition comprising an organic semiconductor and a compound according to claim 1 .

8. A composition according to claim 7 wherein the organic semiconductor is a semiconducting polymer.

9. A composition according to claim 8 wherein the semiconducting polymer is a conjugated polymer.

10. A formulation comprising a compound according to claim 1 and at least one solvent.

11. A formulation according to claim 10 wherein the formulation further comprises an organic semiconductor.

12. A charge transfer salt formed by doping an organic semiconductor with an n-dopant formed from a compound of formula (I) according to claim 1 .

13. A method of forming a charge-transfer salt, the method comprising:
providing a composition comprising the compound according to claim 1 and an organic semiconductor; and
activating the composition to cause n-doping of the organic semiconductor.

14. An organic electronic device comprising a layer comprising a charge-transfer salt according to claim 12 .

15. An organic electronic device according to claim 14 wherein the organic electronic device is an organic light-emitting device comprising an anode, a cathode and a light-emitting layer between the anode and the cathode and wherein the layer comprising the charge-transfer salt is an electron injection layer between the light-emitting layer and the cathode.

16. An organic electronic device according to claim 15 wherein the electron injection layer is in contact with the light-emitting layer.

17. A method of forming a layer of an organic electronic device comprising the step of depositing a layer of a composition comprising a compound according to claim 1 and an organic semiconductor; and activating the composition to cause n-doping of the organic semiconductor.

18. A method according to claim 17 wherein the composition is activated by heating and/or irradiation.

19. A method according to claim 17 wherein the layer of the composition is deposited from a formulation.

Assignees

• Sumitomo Chemical Co

Inventors

• Islam Nazrul
• Tarran William
• Giguere Jean-Benoit

Classifications

• H10K85/654 Primary

  comprising only nitrogen as heteroatom (H10K85/652 takes precedence) · CPC title

• H10K85/60 Primary

  Organic compounds having low molecular weight (H10K85/10 - H10K85/50 take precedence) · CPC title

• C07D249/08 Primary

  1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles · CPC title

• H10K85/631

  Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine · CPC title

• H10K50/171

  Electron injection layers · CPC title