DEHALOGENATION
Post-polymerization treatment including dehalogenation of polymeric materials including debromination of polythiophenes. The polymers can be used in organic electronic devices like OLEDs and OPVs. Improved lifetime and stability can result.
1 . A composition comprising:
at least one polythiophene, wherein the polythiophene has been prepared by steps which comprise a dehalogenation step.
2 . The composition according to claim 1 , wherein the dehalogenation step comprises reducing a weight percentage of bromine.
3 . A composition according to claim 1 , wherein the polythiophene has a halogen content of less than 100 ppm after dehalogenation.
4 . A composition according to claim 1 , wherein the polythiophene has a bromine content of less than 100 ppm after dehalogenation.
5 . A composition according to claim 1 , wherein the polythiophene has a halogen content of less than 10 ppm after dehalogenation.
6 . A composition according to claim 1 , wherein the polythiophene has a bromine content of less than 10 ppm after dehalogenation.
7 . A composition according to claim 1 , wherein the polythiophene is a regioregular polythiophene.
8 . A composition according to claim 1 , wherein the polythiophene is a 3,4-substituted dialkoxypolythiophene.
9 . A composition according to claim 1 , wherein the polythiophene is a soluble polythiophene.
10 . A composition according to claim 1 , wherein the dehalogenation is carried out with use of a magnesium reagent.
11 . A composition according to claim 1 , wherein the dehalogenation is carried out with use of a magnesium reagent coupled with an activation agent.
12 . A composition according to claim 1 , wherein the dehalogenation is carried out with use of a Grignard reagent coupled with an activation agent.
13 . A composition according to claim 1 , wherein the dehalogenation is carried out with use of a Grignard reagent coupled with a lithium activation agent.
14 . A composition according to claim 1 , wherein the dehalogenation step is carried out as part of polymerization of the polythiophene.
15 . A composition according to claim 1 , wherein the dehalogenation step is carried out after polymerization of the polythiophene is substantially complete but before workup of the polythiophene.
16 . A composition according to claim 1 , wherein the dehalogenation step is carried out after polymerization of the polythiophene is substantially complete and after the polythiophene has been purified and redissolved.
17 . A composition according to claim 1 , wherein dehalogenation is carried out to reduce halogen levels such that a parameter in an organic electronic device is improved by at least 10% as a result of dehalogenation and use of the dehalogenated polymer in the device.
18 . A composition according to claim 1 , wherein dehalogenation is carried out to reduce halogen levels such that a parameter in an organic electronic device is improved by at least 25% as a result of dehalogenation and use of the dehalogenated polymer in the device.
19 . A composition according to claim 1 , wherein dehalogenation is carried out to reduce halogen levels such that a parameter in an organic electronic device is improved by at least 50% as a result of dehalogenation and use of the dehalogenated polymer in the device.
20 . A composition according to claim 1 , wherein dehalogenation is carried out to reduce halogen levels such that a parameter in an organic electronic device is improved by at least 75% as a result of dehalogenation and use of the dehalogenated polymer in the device.
21 . A composition comprising:
at least one polythiophene, wherein the polythiophene has been prepared by steps which comprise a dehalogenation step, and at least one solvent for the polymer.
22 . The composition of claim 21 , wherein the solvent is an organic solvent.
23 . The composition of claim 21 , wherein the solvent is water.
24 . The composition of claim 21 , wherein the solvent is a non-halogenated solvent.
25 . The composition of claim 21 , wherein the solvent is a halogenated solvent.
26 . (canceled)
27 . The composition of claim 21 , wherein the polythiophene has a halogen content before dehalogenation of at least 1,000 ppm, and a halogen content after dehalogenation of less than 100 ppm (by weight).
28 . (canceled)
29 . (canceled)
30 . The composition of claim 21 , wherein the polythiophene is stable in the solvent from precipitation or gellation for at least seven days at 25° C.
31 . A method comprising:
dehalogenating at least one polythiophene.
32 . The method of claim 31 , wherein the dehalogenating is carried out as the polythiophene is being prepared by polymerization.
33 . The method of claim 31 , wherein the dehalogenating is carried out after the polythiophene has been prepared by polymerization.
34 . The method of claim 31 , wherein the dehalogenating is carried out after the polythiophene has been prepared by polymerization and after the polythiophene has been purified and redissolved.
35 . The method of claim 31 , wherein dehalogenating is carried out is carried out with use of a magnesium reagent.
36 . The method of claim 31 , wherein dehalogenating is carried out is carried out with use of a magnesium reagent coupled with an activation agent.
37 . The method of claim 31 , wherein the dehalogenation is a debromination.
38 . (canceled)
39 . The method of claim 31 , wherein the dehalogenation results in a halogen content of less than 100 ppm.
40 . The method of claim 31 , wherein the dehalogenation results in a bromine content of less than 100 ppm.
41 . A device comprising:
a substrate,
a plurality of layers disposed on the substrate,
wherein at least one of the layers comprise at least one polythiophene which has been prepared by a dehalogenation step.
42 . The device of claim 41 , wherein the substrate and layers form an organoelectronic device.
43 - 48 . (canceled)
49 . The device according to claim 41 , wherein the dehalogenation improves at least one device performance parameter by at least 10%.
50 . The device according to claim 41 , wherein the dehalogenation improves at least one device performance parameter by at least 10%, and the device performance parameter is a lifetime.
51 - 59 . (canceled)