Electrically conductive polymer compositions
View Patent ↗The present invention relates to electrically conductive polymer compositions, and their use in organic electronic devices. The electrically conductive polymer compositions include an intrinsically conductive polymer having at least one monomer unit derived from Formula I: where: Q=N, CR 5 X=N, CR 6 Z=NH, S, O, Se, Te R 1 through R 4 can be H, F, Cl, C 1 -C 24 alkyl, C 2 -C 24 alkenyl, aryl, C 1 -C 10 alkoxy, C 1 -C 10 alkylseleno, C 1 -C 10 alkylthio, C 1 -C 10 alkylsilyl, NH 2 , or C 1 -C 10 dialkylamino, where adjacent R groups can join together to form a 5- or 6-membered aliphatic or aromatic rings, with the proviso that at least one of R 1 through R 4 is NH 2 , and at least one of R 1 through R 6 is H, and. R 5 and R 6 can be H, C 1 -C 24 alkyl, C 2 -C 24 alkenyl, and aryl. The electrically conducting polymer is doped with a non-fluorinated acid polymer.
1. A polymer composition comprising an intrinsically conductive polymer doped with a non-fluorinated acid polymer, wherein the conductive polymer has at least one monomer unit derived from Formula I:
where:
Q=N, CR 5
X=N, CR 6
Z=NH, S, O, Se, Te
R 1 through R 4 are the same or different and are selected from the group consisting of H, F, Cl, C 1 -C 24 alkyl, C 2 -C 24 alkenyl, aryl, C 1 -C 10 alkoxy, C 1 -C 10 alkylseleno, C 1 -C 10 alkylthio, C 1 -C 10 alkylsilyl, NH 2 , and C 1 -C 10 dialkylamino, where adjacent R groups can join together to form a 5- or 6-membered aliphatic or aromatic rings, with the proviso that at least one of R 1 through R 4 is NH 2 , and at least one of R 1 through R 6 is H, and;
R 5 and R 6 are the same or different and are selected from the group consisting of H, C 1 -C 24 alkyl, C 2 -C 24 alkenyl, and aryl.
2. The composition of claim 1 , wherein one of R 1 and R 4 is NH 2 , and R 2 and R 3 are H.
3. The composition of claim 1 , wherein Z is selected from NH and S.
4. The composition of claim 1 , wherein Q=X═CH.
5. The composition of claim 1 , wherein the monomer unit is derived from a monomer is selected from the group consisting of Formulae Ia through If:
6. The composition of claim 1 , wherein the non-fluorinated acid polymer is selected from the group consisting of poly(styrenesulfonic acid), poly(2-acrylamido-2-methyl-1-propanesulfonic acid), and mixtures thereof.
7. The composition of claim 1 , further comprising a fluorinated acid polymer.
8. The composition of claim 7 , wherein the fluorinated acid polymer has a fluorinated olefin backbone and pendant groups selected from the group consisting of fluorinated ether sulfonate, fluorinated ester sulfonate, fluorinated ether sulfonimide, and combinations thereof.
9. The composition of claim 7 , wherein the fluorinated acid polymer is selected from the group consisting of a copolymer of 1,1-difluoroethylene and 2-(2,2-difluoro-2-(trifluoromethyl)allyloxy)-1,1,2,2-tetrafluoroethanesulfonic acid; a copolymer of ethylene and 2-(2-(1,2,2-trifluorovinyloxy)-1,1,2,3,3,3-hexafluoropropoxy)-1,1,2,2-tetrafluoroethanesulfonic acid; and combinations thereof.
10. The composition of claim 7 , wherein the fluorinated acid polymer has Formula XI:
where:
R 16 is a fluorinated alkyl or a fluorinated aryl group;
a, b, c, d, and e are each independently 0 or an integer from 1 to 3; and
n is at least 4.
11. The composition of claim 7 , wherein the fluorinated acid polymer is a copolymer of TFE (tetrafluoroethylene) and PSEPVE (3,6-dioxa-4-methyl-7-octenesulfonic acid.
12. An aqueous dispersion of the composition of claim 1 .
13. An aqueous dispersion of the composition of claim 7 .
14. An electronic device comprising at least one buffer layer comprising the polymer composition of claim 1 .
15. An electronic device comprising at least one buffer layer comprising the polymer composition of claim 7 .