Patent ID: 8519090
Filing Date: 2013-08-27
Classification: C07D,C09K

Abstract:
1. A conjugated polymer, comprising a fully conjugated polymeric sequence of at least two alternating triads comprising: a first repeating unit selected from dioxythiophene, dioxyfuran, dioxypyrrole, dioxyselenophene, or any combination thereof; and a second repeating unit selected from an aromatic molecule, thiophene, furan, pyrrole, selenophene, or any combination thereof, wherein the conjugated polymer is yellow in its neutral state, having an absorption maximum between 300 and 500 nm that upon oxidation is transmissive between 400-750 nm, wherein the conjugated polymeric sequence has the structure: and, optionally, a second conjugated polymeric sequence of the structure: where A is an aromatic unit, thiophene unit, furan unit, pyrrole unit, selenophene unit, or any combination thereof; n is 2 to 200,000; X is S, Se, O, or NR; x is 0 or 1; y is 0 or 1; R, R 9 , and R 10 are independently H, C 1 -C 30 alkyl, C 2 -C 30 alkenyl, C 2 -C 30 alkynyl, C 6 -C 14 aryl, C 7 -C 30 arylalkyl, C 8 -C 30 arylalkenyl, C 8 -C 30 arylalkynyl, C 2 -C 30 alkylester, C 7 -C 15 arylester, C 8 -C 30 alkylarylester, C 3 -C 30 alkenylester, C 3 -C 30 alkynylester, NH 2 , C 1 -C 30 alkylamino, C 6 -C 14 arylamino, C 7 -C 30 (arylalkyl)amino, C 2 -C 30 alkenylamino, C 2 -C 30 alkynylamino, C 8 -C 30 (arylalkenyl)amino, C 8 -C 30 (arylalkynyl)amino, C 2 -C 30 dialkylamino, C 12 -C 28 diarylamino, C 4 -C 30 dialkenylamino, C 4 -C 30 dialkynylamino, C 7 -C 30 aryl(alkyl)amino, C 7 -C 30 di(arylalkyl)amino, C 8 -C 30 alkyl(arylalkyl)amino, C 15 -C 30 aryl(arylalkyl)amino, C 8 -C 30 alkenyl(aryl)amino, C 8 -C 30 alkynyl(aryl)amino C(O)NH 2 (amido), C 2 -C 30 alkylamido, C 7 -C 14 arylamido, C 8 -C 30 (arylalkyl)amido, C 2 -C 30 dialkylamido, C 12 -C 28 diarylamido, C 8 -C 30 aryl(alkyl)amido, C 15 -C 30 di(arylalkyl)amido, C 9 -C 30 alkyl(arylalkyl)amido, C 16 -C 30 aryl(arylalkyl)amido, thiol, C 1 -C 30 alkylhydroxy, C 6 -C 14 arylhydroxy, C 7 -C 30 arylalkylhydroxy, C 3 -C 30 alkenylhydroxy, C 3 -C 30 alkynylhydroxy, C 8 -C 30 arylalkenylhydroxy, C 8 -C 30 aryl alkynylhydroxy, C 3 -C 30 polyether, C 3 -C 30 polyetherester, C 3 -C 30 polyester C 3 -C 30 polyamino, C 3 -C 30 polyaminoamido, C 3 -C 30 polyaminoether, C 3 -C 30 polyaminoester, C 3 -C 30 polyamidoester, C 3 -C 30 alkylsulfonic acid, C 3 -C 30 alkylsulfonate salt, C 1 -C 30 carboxylate salt, C 1 -C 30 thiocarboxylate salt, C 1 -C 30 dithiocarboxylate salt, or C 3 -C 30 alkyl C 1 -C 4 trialkyammonium salt and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are independently H, C 1 -C 30 alkyl, C 2 -C 30 alkenyl, C 2 -C 30 alkynyl, C 6 -C 14 aryl, C 7 -C 30 arylalkyl, C 8 -C 30 arylalkenyl, C 8 -C 30 arylalkynyl, hydroxy, C 1 -C 30 alkoxy, C 6 -C 14 aryloxy, C 7 -C 30 arylalkyloxy, C 2 -C 30 alkenyloxy, C 2 -C 30 alkynyloxy, C 8 -C 30 aryl alkenyloxy, C 8 -C 30 arylalkynyloxy, CO 2 H, C 2 -C 30 alkylester, C 7 -C 15 arylester, C 8 -C 30 alkylarylester, C 3 -C 30 alkenylester, C 3 -C 30 alkynylester, NH 2 , C 1 -C 30 alkylamino, C 6 -C 14 arylamino, C 7 -C 30 (arylalkyl)amino, C 2 -C 30 alkenylamino, C 2 -C 30 alkynylamino, C 8 -C 30 (arylalkenyl)amino, C 8 -C 30 (arylalkynyl)amino, C 2 -C 30 dialkylamino, C 12 -C 28 diarylamino, C 4 -C 30 dialkenylamino, C 4 -C 30 dialkynylamino, C 7 -C 30 aryl(alkyl)amino, C 7 -C 30 di(arylalkyl)amino, C 8 -C 30 alkyl(arylalkyl)amino, C 15 -C 30 aryl(arylalkyl)amino, C 8 -C 30 alkenyl(aryl)amino, C 8 -C 30 alkynyl(aryl)amino, C(O)NH 2 (amido), C 2 -C 30 alkylamido, C 7 -C 14 arylamido, C 8 -C 30 (arylalkyl)amido, C 2 -C 30 dialkylamido, C 12 -C 28 diarylamido, C 8 -C 30 aryl(alkyl)amido, C 15 -C 30 di(arylalkyl)amido, C 9 -C 30 alkyl(arylalkyl)amido, C 16 -C 30 aryl(arylalkyl)amido, thiol, C 1 -C 30 hydroxyalkyl, C 6 -C 14 hydroxyaryl, C 7 -C 30 hydroxyarylalkyl, C 3 -C 30 hydroxyalkenyl, C 3 -C 30 hydroxyalkynyl, C 8 -C 30 hydroxyarylalkenyl, C 8 -C 30 hydroxyarylalkynyl, C 3 -C 30 polyether, C 3 -C 30 polyetherester, C 3 -C 30 polyester, C 3 -C 30 polyamino, C 3 -C 30 polyaminoamido, C 3 -C 30 polyaminoether, C 3 -C 30 polyaminoester, C 3 -C 30 polyamidoester, C 3 -C 30 alkylsulfonic acid, C 3 -C 30 alkylsulfonate salt, C 1 -C 30 carboxylate salt, C 1 -C 30 thiocarboxylate salt, C 1 -C 30 dithiocarboxylate salt or C 3 -C 30 alkylC 1 -C 4 trialkyammonium salt, and wherein the aromatic unit, thiophene unit, furan unit, pyrrole unit comprises: where: X is NR′, PR′, S, O, Se, SOx, CR2, SiR′2, GeR′2, or BR′, where x=1 or 2; X′ is NR′, O, Se, or S; where R′ is H, C1-C30 alkyl, C2-C30 alkenyl, C2-C30 alkynyl, C6-C14 aryl, C7-C30 arylalkyl, C8-C30 arylalkenyl, C8-C30 arylalkynyl, C1-C30 hydroxyalkyl, C6-C14 hydroxyaryl, C7-C30 hydroxyarylalkyl, C3-C30 hydroxyalkenyl, C3-C30 hydroxyalkynyl, C8-C30 hydroxyarylalkenyl, C8-C30 hydroxyarylalkynyl, C3-C30 polyether, C3-C30 polyetherester, C3-C30 polyester, C3-C30 polyamino, C3-C30 polyaminoamido, C3-C30 polyaminoether, C3-C30 polyaminoester, C3-C30 polyamidoester, C3-C30alkylsulfonic acid, C3-C30alkylsulfonate salt, C1-C30 alkylcarboxylate salt, C1-C30 alkylthiocarboxylate salt, C1-C30 alkyldithiocarboxylate salt or C3-C30 alkyl C1-C4 trialkyammonium salt; R″ is independently H, C1-C30 alkyl, C3-C30 alkenyl, C2-C30 alkynyl, C6-C14 aryl, C7-C30 arylalkyl, C8-C30 arylalkenyl, C8-C30 arylalkynyl; and R is independently H, C1-C30 alkyl, C2-C30 alkenyl, C2-C30 alkynyl, C6-C14 aryl, C7-C30 arylalkyl, C8-C30 arylalkenyl, C8-C30 arylalkynyl, hydroxy, C1-C30 alkoxy, C6-C14 aryloxy, C7-C30 arylalkyloxy, C2-C30 alkenyloxy, C2-C30 alkynyloxy, C8-C30 arylalkenyloxy, C8-C30 arylalkynyloxy, CO2H, C2-C30 alkylester, C7-C15 arylester, C8-C30 alkylarylester, C3-C30 alkenylester, C3-C30 alkynylester, NH2, C1-C30 alkylamino, C6-C14 arylamino, C7-C30 (arylalkyl)amino, C2-C30 alkenylamino, C2-C30 alkynylamino, C8-C30 (arylalkenyl)amino, C8-C30 (arylalkynyl)amino, C2-C30 dialkylamino, C12-C28 diarylamino, C4-C30 dialkenylamino, C4-C30 dialkynylamino, C7-C30 aryl(alkyl)amino, C7-C30 di(arylalkyl)amino, C8-C30 alkyl(arylalkyl)amino, C15-C30 aryl(arylalkyl)amino, C8-C30 alkenyl(aryl)amino, C8-C30 alkynyl(aryl)amino C(O)NH2 (amido), C2-C30 alkylamido, C7-C14 arylamido, C8-C30 (arylalkyl)amido, C2-C30 dialkylamido, C12-C28 diarylamido, C8-C30 aryl(alkyl)amido, C15-C30 di(arylalkyl)amido, C9-C30 alkyl(arylalkyl)amido, C16-C30 aryl(arylalkyl)amido, thiol, C1-C 30 hydroxyalkyl, C6-C14 hydroxyaryl, C7-C30 hydroxyarylalkyl, C3-C30 hydroxyalkenyl, C3-C30 hydroxyalkynyl, C8-C30 hydroxyarylalkenyl, C8-C30 hydroxyarylalkynyl, C3-C30 polyether, C3-C30 polyetherester, C3-C30 polyester, C3-C30 polyamino, C3-C30 polyaminoamido, C3-C30 polyaminoether, C3-C30 polyaminoester, C3-C30 polyamidoester, C3-C30 alkylsulfonic acid, C3-C30alkylsulfonate salt, C1-C30 carboxylate salt, C1-C30 thiocarboxylate salt, C1-C30 dithiocarboxylate salt, or C3-C30 alkylC1-C4 trialkyammonium salt.