Polthiophenes and devices thereof
View Patent ↗Polythiophenes of the formula wherein R is a side chain; m is the number of substituents; A is a divalent linkage; x, y and z represent, respectively, the numbers of R substituted thienylene, unsubstituted thienylene, and divalent linkages A in the monomer segment with z being either 0 or 1; and n represents the number of the repeating monomer segments in the polymer chain or the degree of polymerization.
1. Polythiophenes selected from the group consisting of polythiophenes (II-a) through (II-n)
wherein n represents the degree of polymerization of from about 5 to about 5,000, and the polythiophene exhibits a number average molecular weight (M n ) of from about 2,000 to about 100,000, a weight average molecular weight (M w ) of from about 4,000 to about 500,000, M n and M w being measured by gel permeation chromatography using polystyrene standards, and wherein said polythiophenes possess a conductivity of from about 10 −6 to about 10 −9 S/cm.
2. Polythiophenes selected from the group consisting of polythiophenes (II-a) through (II-e)
wherein n represents the degree of polymerization of from about 5 to about 5,000, and the polythiophene exhibits a number average molecular weight (M n ) of from about 2,000 to about 100,000, a weight average molecular weight (M w ) of from about 4,000 to about 500,000, M n and M w being measured by gel permeation chromatography using polystyrene standards, and wherein said polythiophenes possess a conductivity of from about 10 −6 to about 10 −9 S/cm.
3. Polythiophenes of the formula
wherein R is alkoxyalkyl, siloxy substituted alkyl, a perhaloalkyl, or a polyether; a is an integer of from about 0 to about 5; b, c, and d are integers of from about 1 to about 5; and n represents the degree of polymerization of from about 5 to about 5,000; the number average molecular weight (M n ) of the polythiophenes is from about 2,000 to about 100,000, and the weight average molecular weight (M w ) is from about 4,000 to about 500,000, each measured by gel permeation chromatography using polystyrene standards, and wherein said polythiophenes possess a conductivity of from about 10 −6 to about 10 −9 S/cm.
4. Polythiophenes of the formula
wherein R is alkyl containing from 1 to about 20 carbon atoms; a is an integer of from about 0 to about 5; b, c, and d are integers of from about 1 to about 5; and n represents the degree of polymerization of from about 10 to about 1,000; the number average molecular weight (M n ) of the polythiophenes is from about 4,000 to about 50,000, and the weight average molecular weight (M w ) is from about 5,000 to about 100,000, each measured by gel permeation chromatography using polystyrene standards, and wherein said polythiophenes possess a conductivity of from about 10 −6 to about 10 −9 S/cm.
5. Polythiophenes of the formula
wherein R is a perfluoroalkyl of about 2 to about 15 carbon atoms; a is an integer of from about 0 to about 5; b, c, and d are integers of from about 1 to about 5; and n represents the degree of polymerization of from about 5 to about 5,000; the number average molecular weight (M n ) of the polythiophenes is from about 2,000 to about 100,000, and the weight average molecular weight (M w ) is from about 4,000 to about 500,000, each measured by gel permeation chromatography using polystyrene standards, and wherein said polythiophenes possess a conductivity of from about 10 −6 to about 10 −9 S/cm.
6. Polythiophenes of the formula
wherein R is a siloxyalkyl of trimethylsiloxyalkyl or tricthylsiloxyalkyl, the alkyl optionally containing from about 4 to about 10 carbon atoms, and which alkyl is butyl, pentyl, hexyl, heptyl, or octyl; a is an integer of from about 0 to about 5; b, c, and d are integers of from about 1 to about 5; and n represents the degree of polymerization of from about 5 to about 5,000; the number average molecular weight (M n ) of the polythiophenes is from about 2,000 to about 100,000, and the weight average molecular weight (M w ) is from about 4,000 to about 500,000, each measured by gel permeation chromatography using polystyrene standards, and wherein said polythiophenes possess a conductivity of from about 10 −6 to about 10 −9 S/cm.
7. Polythiophenes of the formula
wherein R is a side chain; a is an integer of from about 0 to about 5; b, c, and d are integers of from about 1 to about 5; and n represents the degree of polymerization of from about 10 to about 1,000; the number average molecular weight (M n ) of the polythiophenes is from about 2,000 to about 100,000, and the weight average molecular weight (M w ) is from about 4,000 to about 500,000, each measured by gel permeation chromatography using polystyrene standards, and wherein said polythiophenes possess a conductivity of from about 10 −6 to about 10 −9 S/cm.
8. Polythiophenes selected from the group consisting of polythiophenes (II-a) through (II-f)
wherein n represents the degree of polymerization of from about 100 to about 4,000, and the polythiophene exhibits a number average molecular weight (M n ) of from about 2,000 to about 100,000, a weight average molecular weight (M w ) of from about 4,000 to about 500,000, M n and M w being measured by gel permeation chromatography using polystyrene standards, and wherein said polythiophenes possess a conductivity of from about 10 −6 to about 10 −9 S/cm.
9. Polythiophenes in accordance with claim 7 wherein R is alkyl containing from about 1 to about 20 carbon atoms; or wherein R is alkyl containing from about 6 to about 12 carbon atoms.
10. Polythiophenes in accordance with claim 7 wherein R is butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, or dodecyl.
11. Polythiophenes in accordance with claim 7 wherein b and d are from about 1 to about 5.
12. Polythiophenes in accordance with claim 7 wherein b and d are from about 1 to about 3.
13. Polythiophenes in accordance with claim 7 wherein a is from about 0 to about 5, and c is about 1 to about 5, or wherein a is about 0 to about 3, and c is about 1 to about 3.
14. A process for the preparation of polythiophenes comprising reacting about 1 molar equivalent of a suitable monomer in an organic solvent with about 1 to about 5 molar equivalents of a ferric chloride at a temperature of from about 25° C. to about 80° C., and which polythiophenes are of the formula
wherein a, b, c, and d represent the number of segments; each R is a side chain, and n represents the degree of polymerization or the number of repeating segments.
15. A process in accordance with claim 14 wherein said R side chain is alkyl, substituted alkyl, or perhaloalkyl.
16. A process in accordance with claim 15 wherein alkyl contains from 1 to about 25 carbon atoms or from 4 to about 15 carbon atoms; wherein substituted alkyl is alkoxy alkyl, or siloxy substituted alkyl; and said perhaloalkyl is a perfluoroalkyl.