Neutral and electrically conductive poly(heterocyclic vinylenes) and processes for preparing same

Claim 2

An electrically conductive polymer comprising a polymer which comprises recurring units selected from the group consisting of those of the following formulae VIII-XIV: ##STR5## wherein: m, and the sum of n, o, and p, are the same or different and are natural numbers greater than about 100; q is a natural number from 0 and 4; R 1 to R 14 are the same or different at each occurrence and are hydrogen, alkyl, alkenyl, alkoxy, alkanoyl, alkylthio, aryloxy, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkylaryl, arylalkyl, cycloalkyl, alkylsulfinyl, alkylsulfonyl, arylalkylamino, aryl arylthio, alkylamino, dialkylamino, arylamino, diarylamino, cycloalkenyl, arylsulfinyl, arylsulfonyl, or alkyl substituted with a sulfonic acid, halo, nitro, amino, cyano, carboxylic acid, phosphoric acid or epoxy moiety or any of X 1 and X 2 are the same or different and are divalent S, O, Se, NR 15 or PR 15 , wherein R 15 is hydrogen, alkyl, alkyaryl, arylalkyl, or aryl, doped with a dopant.

Claim 3

An electrically conductive polymer according to claim 1 wherein said doped polymer has an electrical conductivity equal to or greater than about 10 -2 ohm -1 cm -1 .

Claim 4

An electrically conductive polymer according to claim 1 wherein said conductivity is equal to or greater than about 10 -1 ohm -1 cm -1 .

Claim 5

An electrically conductive polymer according to claim 1 wherein said conductivity is greater than about 10 1 ohm -2 cm -1 .

Claim 6

An electrically conductive polymer according to claim 1 wherein said conductivity is equal to or greater than about 10 2 ohm -1 cm -1 .

Claim 7

An electrically conductive polymer according to claim 1 with a doping level of from about 10 -2 to 33 mole %.

Claim 8

An electrically conductive polymer according to claim 6 with doping level of from about 5 to about 25 mole %.

Claim 9

An electrically conductive polymer according to claim 1 wherein: R 1 to R 4 are the same or different at each occurrence and are hydrogen; alkyl containing from 1 to about 12 carbon atoms; phenyl; alkenyl containing from 2 to about 12 carbon atoms; alkylphenyl or phenylalkyl each containing from about 7 to about 18 carbons atoms; alkylthio or alkoxy each containing from 1 to about 12 carbon atoms; alkylamino, dialkylamino, dialkylamino, arylamino and alkylarylamino; or substituted phenyl or substituted alkyl having from 1 to about 12 carbon atoms wherein permissible substitutents are epoxy, nitro, cyano, amino sulfonic acid, phosphoric acid, carboxylic acid or halo groups, or any of R 1 and R 2 , or R 3 and R 4 substituents taken together may form an alkylene or alkenylene chain having from 2 to 20 carbon atoms completing a 4, 5 or 6 membered ring system which may include one or more heteroatoms of divalent oxygen or sulfur; R 5 to R 12 are the same or different at each occurrence and are hydrogen, substituted or substituted alkyl having from 1 to about 12 carbon atoms, substituted or unsubstituted phenyl, or alkylthio or alkoxy each having from 1 to about 12 carbon atoms; or any of R 5 and R 6 , or R 7 and R 8 , or R 9 and R 10 or R 11 and R 12 substituents taken together may form an alkylene chain having 2 to about 20 carbon atoms completing a 4, 5 or 6 membered ring system which may include one or more heteroatoms of oxygen, nitrogen or sulfur; and X 1 and X 2 are the same or different and are divalent oxygen, sulfur or NR 15 wherein R 15 is hydrogen

Claim 10

An electrically conductive polymer according to claim 8 wherein: R 1 , R 2 , R 3 , and R 4 are the same or different at each occurrence and are hydrogen, alkoxy, alkythio or alkyl.

Claim 11

An electrically conductive polymer according to claim 9 wherein R 1 , R 2 , R 3 and R 4 are hydrogen.

Claim 12

An electrically conductive polymer according to claim 9 wherein R 1 , R 2 , R 3 and R 4 are the same or different and are hydrogen, alkyl and alkoxy.

Claim 13

A polymer according to claim 9 wherein no more than about two of R 1 , R 2 , R 3 or R 4 is alkyl or alkoxy.

Claim 14

An electrically conductive polymer according to claim 9 wherein R 1 is alkoxy or alkyl having 1 to about 12 carbon atoms; R 3 is hydrogen or alkyl having 1 to about 12 carbon atoms; and R 2 and R 4 are hydrogen.

Claim 15

An electrically conductive polymer according to claim 8 wherein X 1 and X 2 are sulfur.

Claim 16

An electrically conductive polymer according to claim 1 wherein R 5 to R 12 are the same or different at each occurrence and are hydrogen or alkyl having from 1 to about 12 carbon atoms.

Claim 17

An electrically conductive polymer according to claim 16 wherein at least one of R 5 to R 12 are hydrogen.

Claim 18

An electrically conductive polymer of claim 6 wherein X 1 , or X 2 is NR 15 .

Claim 19

An electrically conductive polymer according to claim 17 wherein X and X 2 are NR 15 , wherein R 15 hydrogen or alkyl from about 1 to about 12 carbon atoms, phenyl or alkylphenyl of about 6 to about 12 carbon atoms, being the same or different at each occurrence.

Claim 20

An electrically conductive polymer according to claim 1 wherein m and the sum of n, o, and p are the same or different and are greater than about 200.

Claim 21

An electrically conductive polymer according to claim 19 is wherein m, and the sum of n, o, and p are the same or different and are greater than about 500.

Claim 22

An electrically conductive polymer of claim 1 comprising recurring units selected from the group consisting of those of the formula: ##STR6##

Claim 23

An electrically conductive polymer of claim 21 wherein m is a natural number equal to or greater than about 200; R 1 , R 2 , R 3 and R 4 are the same or different at each occurrence and are hydrogen, or alkyl or alkoxy having from 1 to about 12 carbons; X 1 and X 2 are sulfur; and R 5 and R 6 are the same or different at each occurrence and are hydrogen or alkyl having from 1 to about 12 carbons.

Claim 24

An electrically conductive polymer according to claim 21 wherein m is equal to or greater than about 500.

Claim 25

An electrically conductive polymer according to claim 21 wherein: R 1 is alkoxy or alkyl having from 1 to about 12 carbon atoms; R 3 is hydrogen or alkyl having from 1 to about 12 carbon atoms; and R 2 and R 4 are hydrogen.

Claim 26

Polymer according to claim 21 wherein X 1 and X 2 are NR 15 .

Claim 27

Polymer according to claim 21 wherein X 1 , or X 2 is NR 15 where R 15 is the same or different at each occurrence and is hydrogen, alkyl from about 1 to about 12 carbon atoms, aryl or alkylaryl of about 6 to about 12 carbon atoms.

Claim 28

An electrically conductive polymer according to claim 21 selected from the group consisting of poly(2,5-thienylene vinylene), poly(3-methoxy-2,5-thienylene vinylene), poly(3-butyl-2,5-thienylene vinylene), and poly(3-butyl-2,5-thienylene-CO-3-methyl-2,5-thienylene vinylene).

Claim 29

An electrically conductive solution comprising: (a) an organic solvent; and (b) a doped electrically conductive polymer according to claim 1.

Claim 30

A method of forming a conductive article which comprises the steps of (a) forming the solution of claim 28; and (b) removing from the solution the solvent as the polymer solute solidifies to form said conductive article.

Claim 31

A conductive article manufactured in accordance with the method of claim 28.

Claim 32

An electrically conductive polymer according to claim 1 wherein X 1 and X 2 are the same or different and are oxygen or sulfur.

Claim 33

An electrically conductive conductive polymer according to claim 8 wherein X 1 and X 2 are the same or different and are oxygen or sulfur.