Benzodithiophene based materials compositions

1. A polymer semiconductor containing a polythiophene having an M n , from about 1,000 to about 400,000 Daltons and derived from benzodithiophene monomer segments of Formula (1)

and at least one aromatic or heteroaromatic electron acceptor compound X,

wherein R 1 and R 2 are side chains independently selected from the group consisting of a hydrogen atom, a hydrocarbon group, a heteroatom selected from the group consisting of fluorine, bromine, chlorine, iodine, sulfur and nitrogen, and combinations thereof, and

wherein the electron acceptor compound X is selected from the group consisting of electron acceptor compounds of:

wherein R 3 is a side chain independently selected from the group consisting of a hydrogen atom, a hydrocarbon group, a heteroatom and combinations thereof;

2. The polymer semiconductor of claim 1 , wherein R 1 and R 2 are a hydrocarbon group.

3. The polymer semiconductor of claim 2 , wherein the hydrocarbon group is a linear or branched alkyl group or a substituted or unsubstituted aryl group.

4. The polymer semiconductor of claim 1 , wherein the polymer semiconductor is a polymer of Formula (2)

wherein n is the number of repeating units of from about 2 to about 5000.

5. The polymer semiconductor of claim 4 , wherein n is the number of repeating units of from about 5 to about 800.

6. A method of producing a polymer semiconductor containing a polythiophene having an M n , from about 1,000 to about 400,000 Daltons, the method comprising:

reacting a benzoquinone-dithiophene with a reagent of the formula M-R′ to form an intermediate, wherein M is MgX′ or Li, X′ is a halogen, and R′ is a hydrocarbon group;

reducing the resulting intermediate to form a 4,8-disubstituted benzodithiophene of Formula (1):

substituting the 2 and 6 positions of the benzodithiophene with at least one boron reagent or at least one halogen atom;

copolymerizing an aromatic or heteroaromatic electron acceptor compound X to the 2 and 6 positions of the benzodithiophene to obtain a repeating unit;

wherein the aromatic or heteroaromatic electron acceptor compound X is selected from the group consisting of electron acceptor compounds of:

wherein R 3 is a side chain independently selected from the group consisting of a hydrogen atom, a hydrocarbon group, a hereatom and combinations thereof;

copolymerizing the repeating units to obtain the polymer semiconductor.

7. The method of claim 6 , wherein the aromatic or heteroaromatic electron acceptor compound X is substituted with at least one boron reagent or at least one halogen atom.

8. The method of claim 6 , wherein the 4,8-disubstituted benzodithiophene of Formula (1) is copolymerized with the aromatic or heteroaromatic electron acceptor compound X at the 2 and 6 positions using a Suzuki-Miyaura polycondensation reaction.

9. An electronic device comprising the polymer semiconductor compound of claim 1 .

10. The electronic device of claim 9 , wherein the electronic device is a thin-film transistor or a photovoltaic device.

11. A polymer semiconductor containing a polythiophene having an M n from about 1,000 to about 400,000 Daltons and derived from benzodithiophene monomer segments of Formula (2)

and at least one aromatic or heteroaromatic electron acceptor compound X,

wherein n is the number of repeating units of from about 2 to about 5000, and

wherein the aromatic electron acceptor or the heteroaromatic electron acceptor compound X is selected from the group consisting of electron acceptor compounds of:

wherein R 3 is a side chain independently selected from the group consisting of a hydrogen atom, a hydrocarbon group, a heteroatom and combinations thereof;

12. The polymer semiconductor of claim 1 , wherein the R 1 and R 2 side chains are each a hydrocarbon group.

13. The polymer semiconductor of claim 1 , wherein the electron acceptor compound X is selected from the group consisting of electron acceptor compounds of: