Doping conjugated polymers and devices
View Patent ↗Compositions comprising at least one hole transport material, such as a conjugated polymer, and at least one dopant, providing improved thermal stability. Compositions can be applied to substrates and used in HIL and HTL layers and organic electronic devices such as light emitting devices such as OLEDs or OPVs. The conjugated polymer can be a polythiophene, including a 3,4-substituted polythiophene or a regioregular polythiophene. The dopant can be a silver salt such as silver tetrakis(pentafluorophenyl)borate. Improved methods of making dopant are provided.
1. A composition comprising: a reaction product of (i) at least one hole transport material, and (ii) at least one silver tetrakis(halogenatedaryl)borate dopant.
2. A composition according to claim 1 , wherein the silver tetrakis(halogenatedaryl)borate dopant is silver tetrakis(pentafluorophenyl)borate dopant.
3. The composition according to claim 1 , wherein the hole transport material is a polymer.
4. The composition according to claim 1 , wherein the hole transport material is a polymer, wherein the polymer is a conjugated polymer or an arylamine polymer, or wherein the polymer is a main chain or side chain hole transporting polymer.
5. The composition according to claim 1 , wherein the hole transport material is a conjugated polymer.
6. The composition of claim 1 , wherein the hole transport material is a polythiophene.
7. The composition according to claim 1 , wherein the hole transport material is a regioregular polythiophene.
8. The composition according to claim 1 , wherein the hole transport material is a conjugated polymer comprising at least one polythiophene comprising an alkoxy substituent at either the 3-position or the 4 position or both.
9. The composition according to claim 1 , wherein the composition further comprises a matrix material.
10. The composition according to claim 1 , wherein the composition further comprises at least one synthetic organic polymer as matrix material.
11. The composition according to claim 1 , wherein the composition further comprises at least one synthetic organic polymer as matrix material, wherein the polymer is an insulating or semiconducting polymer.
12. The composition according to claim 1 , wherein the reaction product is a product of between about 40% and 75% by weight hole transport material and between about 25% and 55% by weight dopant.
13. The composition according to claim 1 , wherein the reaction product is a product of between about 50% and 65% by weight hole transport material and between about 35% and 50% by weight dopant.
14. The composition according to claim 1 , wherein the composition is in the form of a solid powder or is dissolved or dispersed in a solvent ink carrier.
15. The composition of claim 1 , wherein the composition is a solid powder.
16. The composition according to claim 1 , wherein the composition is dissolved or dispersed in a solvent ink carrier without thermal or photo treatment to induce reaction.
17. The composition according to claim 1 , wherein the composition is dissolved or dispersed in a solvent ink carrier which comprises at least one of toluene, xylene(s), tetralene, mesitylene, phenetole, 4-methylanisole, anisole, tetrahydropyran, 3-methoxypropionitrile, 3-ethoxypropionitrile, methyl benzoate, ethyl benzoate, propyleneglycolmethyl ether acetate, 1,2-dimethoxyethane, diethyleneglycoldiethylether, and combinations thereof.
18. The composition according to claim 1 , wherein the composition is dissolved or dispersed in a solvent ink carrier which comprises THP, anisole, dimethoxyethane, ethylbenzoate.
19. The composition according to claim 1 , wherein the composition has a zero valent metal content of 0.5 wt. % or less.
20. The composition according to claim 1 , wherein the composition is substantially free of zero valent metal.
21. The composition of claim 1 , comprising at least one solid powder, wherein the solid powder comprises said reaction product.
22. The composition according to claim 21 , wherein the hole transport material is a conjugated polymer.
23. The composition of claim 21 , wherein the hole transport material is a polythiophene.
24. The composition according to claim 21 , wherein the silver tetrakis(halogenatedaryl)borate dopant is silver tetrakis(pentafluorophenyl)borate.
25. The composition according to claim 21 , wherein the composition is substantially free of zero valent metal.
26. A device comprising the composition of claim 1 , wherein the device is an OLED, OPV, transistor, sensor, capacitor, or battery device.
27. An ink composition comprising the composition of claim 1 and a solvent carrier.
28. A device comprising at least one cathode, at least one anode, at least one light emission layer disposed between the cathode and anode, at least one hole injection layer between the light emission layer and the anode or cathode, wherein the hole injection layer comprises a composition according to claim 1 .
29. The device of claim 28 , wherein the device is an OLED or OPV device.
30. The device of claim 28 , wherein the device is an OLED device.
31. The device of claim 28 , wherein the device further comprises a hole transport layer.
32. The device according to claim 28 , wherein the HIL layer has a thickness of about 5 nm to about 500 nm.
33. The device according to claim 28 , wherein the HIL layer has a thickness of about 5 nm to about 150 nm.
34. The device according to claim 28 , wherein the HIL layer has a thickness of about 20 nm to about 100 nm.
35. The device according to claim 28 , wherein the HIL layer is thermally annealed.
36. The device according to claim 28 , wherein the HIL layer is thermally annealed at temperature of about 25° C. to about 250° C.
37. The device according to claim 28 , wherein the HIL layer is thermally annealed at temperature of about 25° C. to about 250° C. and at reduced pressures of 10 −6 to 760 torr.
38. The device according to claim 28 , wherein the HIL layer is thermally annealed at temperature of about 90° C. to about 170° C. for about 5 to about 15 minutes.
39. The device according to claim 28 , wherein the HIL layer is heated to remove solvent.
40. The device according to claim 28 , wherein the HIL layer does not comprise iodonium salt.