Photocrosslinkable electrically conductive polymers
View Patent ↗Photocrosslinkable electrically conductive polymers and compositions including the polymers are provided. Also, electrically conductive layers or films formed from the compositions, preparation methods of these, and articles including the electrically conductive layers or films are provided. The electrically conductive polymers according to the present disclosure have photoreactive groups that can be crosslinked using like. The electrically conductive polymers can also be dissolved in aqueous solution. These photocrosslinkable and soluble properties allow the electrically conductive polymers to be used in wet processing to make films and/or to be made into a patterned conductive layer or film using a photomask.
1. A copolymer comprising repeating units of Formula 4, Formula 6, Formula 7 and Formula 8:
wherein R 2 , R 2 ′, R 3 and R 3 ′ are independently selected from the group consisting of hydrogen, hydroxyl, alkyl, alkenyl, alkynyl, alkanoyl, alkanoylamino, alkenoyl, alkynoyl, alkoxy, alkoxycarbonyl, alkoxycarbonylamino, alkylamino, alkylaminocarbonyl, dialkylaminocarbonyl, alkylsulfonyl, alkylsulfinyl, sulfonylaminoalkyl, alkylsulfonylaminocarbonyl, aminoalkyl, cyanoalkyl, halogen, haloalkyl, haloalkenyl, haloalkynyl, haloalkanoyl, haloalkenoyl, haloalkynoyl, haloalkoxy, haloalkoxycarbonyl, hydroxyalkyl, oxoalkyl, cycloalkyl, cycloalkenyl, cycloalkanoyl, cycloalkenoyl, cycloalkoxy, cycloalkoxycarbonyl, aryl, arylene, heterocycle, heterocyclyl, heteroaryl, heteroarylene, arylalkyl, heteroarylalkyl, arylalkanoyl, heteroarylalkanoyl, arylalkenoyl, heteroarylalkenoyl, arylalkynoyl, heteroarylalkynoyl, arylalkoxy, heteroarylalkoxy, aryloxy, heteroaryloxy, aryloxycarbonyl, heteroaryloxycarbonyl, arylalkoxycarbonyl, heteroarylalkoxycarbonyl, alkylhio, alkylthioalkyl, arylthio, arylsulfonyl and arylsulfinyl; or, R 2 and R 2 ′ or R 3 and R 3 ′ together form an alkylene or alkenylene chain completing a 3, 4, 5, 6, or 7-membered aromatic or alicyclic ring, and the ring optionally includes one or more divalent nitrogen, sulfur or oxygen atoms; and the substituents are substituted or unsubstituted;
R 4 , and R 4 ′ are independently selected from the group consisting of hydrogen, hydroxyl, alkyl, alkenyl, alkynyl, alkanoyl, alkanoylamino, alkenoyl, alkynoyl, alkoxy, alkoxycarbonyl, alkoxycarbonylamino, alkylamino, alkylaminocarbonyl, dialkylaminocarbonyl, alkylsulfonyl, alkylsulfinyl, sulfonylaminoalkyl, alkylsulfonylaminocarbonyl, aminoalkyl, cyanoalkyl, halogen, haloalkyl, haloalkenyl, haloalkynyl, haloalkanoyl, haloalkenoyl, haloalkynoyl, haloalkoxy, haloalkoxycarbonyl, hydroxyalkyl, oxoalkyl, cycloalkyl, cycloalkenyl, cycloalkanoyl, cycloalkenoyl, cycloalkoxy, cycloalkoxycarbonyl, aryl, arylene, heterocycle, heterocyclyl, heteroaryl, heteroarylene, arylalkyl, heteroarylalkyl, arylalkanoyl, heteroarylalkanoyl, arylalkenoyl, heteroarylalkenoyl, arylalkynoyl, heteroarylalkynoyl, arylalkoxy, heteroarylalkoxy, aryloxy, heteroaryloxy, aryloxycarbonyl, heteroaryloxycarbonyl, arylalkoxycarbonyl, heteroarylalkoxycarbonyl, alkylhio, alkylthioalkyl, arylthio, arylsulfonyl, arylsulfinyl, Y and L-Y, with a proviso that at least one of R 4 and R 4 ′ is Y or L-Y;
X 2 is NH, N, O, S or P;
Y is a photoreactive group;
L is selected from the group consisting of alkylene, alkylene oxide, alkenylene, alkenylene oxide and alkynylene, which is unsubstituted or substituted with alkyl, alkoxy or a combination thereof;
the ratio of the repeating unit of Formula 4 or Formula 6 and the repeating unit of Formula 7 is 1:0.1 to 1:0.5;
the copolymer has a degree of polymerization of 100 to 1,000;
the copolymer is doped with a polymeric acid of formula 8; and
m′ is 100 to 1000.
2. The copolymer of claim 1 , wherein L is selected from the group consisting of C 6 -C 12 alkylene or C 6 -C 12 alkylene oxide, which is unsubstituted or substituted with C 1 -C 12 alkyl, C 1 -C 12 alkoxy or a combination thereof.
3. The copolymer of claim 2 , wherein the repeating unit of formula 6 is 3,4-ethylenedioxythiophene and the copolymer is doped with poly(styrenesulfonate).
4. The copolymer of claim 1 , wherein Y is selected from the group consisting of a cinnamoyl group, a chalcone group, a coumarin group, a maleimide group, an anthracenic group and a pyrimidine group, which is unsubstituted or substituted with at least one substituent having at least one ionic moiety.