Granted Patent B2

US 8,383,454 · App. 13/316,324 · Granted Feb 26, 2013

Abstract

Claims (46)

1. A method comprising:

providing a composition comprising at least one conductive conjugated polymer, at least one semiconducting matrix component that is different from the conductive conjugated polymer, and optionally at least one dopant, wherein the composition comprises less than about 5% (w/w) of an insulating matrix component; and

incorporating the composition into an electronic device.

2. The method of claim 1 , wherein the composition comprises less than about 3% (w/w) of the insulating matrix component, or less than about 1% (w/w) of the insulating matrix component, or less than about 0.1% (w/w) of the insulating matrix component, or less than about 0.01% (w/w) of the insulating matrix component.

3. The method of claim 1 , wherein the conductive conjugated polymer comprises a polythiophene.

4. The method of claim 1 , wherein the conductive conjugated polymer comprises a regioregular polythiophene, or a sulfonated polythiophene, or a sulfonated regioregular poly(3-substituted)thiophene.

5. The method of claim 1 , wherein the composition comprises about 1 wt % to about 99 wt % conductive conjugated polymer with respect to the total amount of conductive conjugated polymer, semiconducting matrix component, and dopant, if present.

6. The method of claim 1 , wherein the semiconducting matrix component is a semiconducting polymer.

7. The method of claim 1 , wherein the semiconducting matrix component is a semiconducting polymer, and wherein the semiconducting polymer comprises a polyaromatic polymer or a polyvinyl aromatic polymer.

8. The method of claim 1 , wherein the semiconducting matrix component is a semiconducting polymer, and wherein the semiconducting polymer comprises polyvinyl naphthalene, polyvinyl anthracene, or polyvinyl carbazole.

9. The method of claim 1 , wherein the semiconducting matrix component is a semiconducting polymer, and wherein the semiconducting polymer comprises polyanthracene or polynaphthalene.

10. The method of claim 1 , wherein the semiconducting matrix component comprises a polymer having one or more repeat units comprising a hole transport compound.

11. The method of claim 1 , wherein the semiconducting matrix component is a semiconducting small molecule.

12. The method of claim 1 , wherein the semiconducting matrix component is a hole transporting compound.

13. The method of claim 1 , wherein the semiconducting matrix component is a polycyclic aromatic compound selected from anthracene, naphthalene and fluorene.

14. The method of claim 1 , wherein the semiconducting matrix component is a triarylamine.

15. The method of claim 1 , wherein the composition comprises about 1 wt % to about 99 wt % semiconducting matrix component with respect to the total amount of conductive conjugated polymer, semiconducting matrix component, and dopant, if present.

16. The method of claim 1 , wherein the dopant is present, and the dopant is a redox dopant.

17. The method of claim 1 , wherein the dopant is present and the dopant is a redox dopant selected from quinones, boranes, carbocations, bora-tetraazapentalenes, aminium or ammonilium salts, sulfonium salts, oxonium salts, selenonoium salts, nitrosonium salts, arsonium salts, phosphonium salts, iodonium salts, metal salts, and combinations thereof.

18. The method of claim 1 , wherein the dopant is present and the dopant is a photoacid.

19. The method of claim 1 , wherein the dopant is present and the dopant is a photoacid that is an iodonium salt represented by

wherein independently R 1 is an optionally substituted aryl group, independently R 2 is an optionally substituted aryl group, and X − is an anion.

20. The method of claim 19 , wherein the iodonium salt is selected from 4-isopropyl-4′-methyldiphenyliodonium tetrakis(pentafluorophenylborate) (IMDPIB(PhF 5 ) 4 ), diphenyliodonium hexafluorophosphate (DPIPF 6 ), diphenyliodonium para-toluene sulfonate (DPITos), bis-(4-tert-butylphenyl)iodonium trifluoromethane sulfonate ( t BDPITFSO 3 ), and diphenyliodonium perfluoro-1-butane sulfonate (DPIPFBSO 3 ).

21. The method of claim 1 , wherein the dopant is present and the dopant is covalently attached to the conductive conjugated polymer.

22. The method of claim 1 , wherein the composition consists essentially of the conductive conjugated polymer, the semiconducting matrix component, and the dopant.

23. The method of claim 1 , further comprising an organic solvent.

24. The method of claim 1 , wherein the composition consists essentially of the conductive conjugated polymer, the semiconducting matrix component, the dopant, and an organic solvent.

25. The method of claim 1 , wherein the incorporating step comprises depositing the composition onto a substrate, and drying the deposited composition to form a hole transport layer or a hole injection layer.

26. The method of claim 25 , wherein the composition is deposited by spin coating, spray coating, inkjet printing, or contact printing.

27. The method of claim 25 , further comprising incorporating another layer into the electronic device by vapor deposition, wherein the electronic device is a hybrid device.

28. The method of claim 25 , wherein the electronic device has an efficiency of at least 4.00% cd/A.

29. The method of claim 25 , wherein the hole transport layer or hole injection layer is about 60 nm to about 200 nm thick.

30. The method of claim 25 , wherein the hole transport layer or hole injection layer is substantially transparent to visible light.

31. The method of claim 1 , wherein the composition is incorporated into a hole transport layer or hole injection layer, and wherein the hole transport layer or hole injection layer leads to an increase in device efficiency of at least 5%.

32. The method of claim 1 , wherein the electronic device is an organic light emitting diode (OLED) or an organic photovoltaic device (OPV).

33. A method comprising:

co-mixing a first composition comprising at least one conductive conjugated polymer and a second composition comprising at least one semiconducting matrix component that is different from the conductive conjugated polymer to form a third composition, wherein the third composition comprises less than about 5% (w/w) of an insulating matrix component.

34. The method of claim 33 , wherein the first composition further comprises at least one dopant.

35. The method of claim 33 , wherein the first composition further comprises at least one solvent.

36. The method of claim 33 , wherein the second composition further comprises at least one solvent.

37. The method of claim 33 , wherein the first composition comprises a regioregular polythiophene and a redox dopant, and the second composition comprises a semiconducting small molecule.

38. The method of claim 33 , wherein the third composition comprises less than about 3% (w/w) of the insulating matrix component, or less than about 1% (w/w) of the insulating matrix component, or less than about 0.1% (w/w) of the insulating matrix component, or less than about 0.01% (w/w) of the insulating matrix component.

39. The method of claim 33 , wherein the co-mixing step comprises (a) combining the conductive conjugated polymer with at least one solvent and at least on dopant to form a doped conductive polymer solution, and (b) adding the semiconducting matrix component to the doped conductive polymer solution.

40. A method comprising:

co-mixing a first composition comprising at least one conductive conjugated polymer and a second composition comprising at least one semiconducting matrix component that is different from the conductive conjugated polymer to form a third composition, wherein the third composition comprises less than about 5% (w/w) of an insulating matrix component; and

depositing the third composition onto a substrate to form a hole transport layer or hole injection layer, wherein the hole transport layer or hole injection layer is incorporated into an electronic device.

Assignments (8)