Method for producing conjugated polymer, conjugated polymer, photoelectric conversion element, solar cell, and solar cell module

1. A method for producing a conjugated polymer, the method comprising:

polymerizing a monomer via a coupling reaction, wherein the coupling reaction is carried out in the coexistence of a combination of a homogeneous transition metal complex catalyst and a heterogeneous transition metal complex catalyst, wherein the monomer is an aromatic compound having formula (A4) or formula (A4′):

wherein:

R 1 and R 2 are each independently a hydrogen atom, a halogen atom, an alkyl group optionally having a substituent, an alkenyl group optionally having a substituent, an alkynyl group optionally having a substituent, or an aromatic group optionally having a substituent, or R 1 and R 33 , or R 2 and R 34 may bond to each other to from a ring;

R 33 and R 34 are each independently a hydrogen atom, a halogen atom, or an organic group having an atom selected from Group 14 elements of the Periodic Table, or may bond to each other to form a ring;

X 1 and X 2 are each independently an active group;

X 12 and X 13 are each independently an atom selected from Group 16 elements;

X 14 a is a group that links the two conjugated systems of five-membered rings bonding thereto or a direct bond.

2. The method of claim 1 , wherein the heterogeneous transition metal complex catalyst comprises a transition metal complex supported by a carrier.

3. The method of claim 1 , wherein each transition metal that constitutes the homogeneous transition metal complex catalyst and the heterogeneous transition metal complex catalyst is a late transition metal.

4. The method of claim 1 , wherein, in formula (A4) and (A4′), X 1 and X 2 are each independently active groups having an atom selected from Li, Mg, Zn, B, and Group 14 elements of the Periodic Table,

wherein when 5 ml of a hexane solution containing 1.0 g of the aromatic compound is charged in a column having an inner diameter of 15 mm and a length of 5 cm with 50 mL of a hexane solution containing 20 g of spherical, neutral silica gel having a particle size of from 63 to 210 μm, and 2 g of anhydrous potassium carbonate, and developed with a developing solvent of hexane at a flow rate of 50 ml/min, the total proportion of aromatic compounds in which the number of the active groups is smaller than the aromatic compound, in the solution having passed through the column in 3 minutes at room temperature is 5 mol % or more relative to the aromatic compound before charged in the column.

5. The method of claim 1 , wherein the compound represented by formula (A4) or formula (A4′) is a compound having formulae (A6) or (A6′):

wherein, in formulae (A6) and (A6′):

R 1 , R 2 , X 1 , X 2 , X 12 , X 13 and X 14 have the same meanings as in the formula (A4); and

the Ring C is a ring optionally having a substituent.

6. The method of claim 5 , wherein the Ring C is a 5-membered single ring, a 6-membered single ring, or a condensed ring of from 2 to 6 such rings.

7. The method of claim 1 , wherein the monomer further comprises an aromatic compound selected from the group consisting of compounds having formulae (A11), (A12), (A13), and (A17):

wherein, in formulae (A11), (A12), (A13), and (A17):

X 3 and X 4 are each a halogen atom, an alkylsulfonyloxy group, or an arylsulfonyloxy group,

wherein in formula (A11):

R 31 and R 32 are each a hydrogen atom, a hydrocarbon group having from 1 to 20 carbon atoms and optionally having a substituent, an aromatic heterocyclic group having from 2 to 20 carbon atoms and optionally having a substituent, an acyl group optionally having a substituent, an alkoxy group optionally having a substituent, or an aryloxy group optionally having a substituent,

wherein in formula (A12):

R 25 and R 26 are each a hydrogen atom, a halogen atom, a hydrocarbon group having from 1 to 20 carbon atoms and optionally having a substituent, an aromatic heterocyclic group having from 2 to 20 carbon atoms and optionally having a substituent, or an acyl group optionally having a substituent; and

R 27 and R 28 are each a hydrogen atom, a halogen atom, a hydrocarbon group having from 1 to 20 carbon atoms and optionally having a substituent, or an aromatic heterocyclic group having from 2 to 20 carbon atoms and optionally having a substituent,

wherein in formula (A13);

Y 1 and Y 2 are each independently an atom selected from Group 15 elements of the Periodic Table; and

R 19 and R 20 are each a hydrogen atom, a halogen atom, or a hydrocarbon group having from 1 to 20 carbon atoms and optionally having a substituent,

wherein in formula (A17):

Y 3 and Y 4 are each independently a nitrogen atom, or a carbon atom having one substituent (C(R 43 )), where R 43 is a hydrogen atom, a halogen atom, a hydrocarbon group having from 1 to 20 carbon atoms and optionally having a substituent, or an aromatic heterocyclic group having from 2 to 20 carbon atoms and optionally having a substituent; and

R 21 and R 22 are each a hydrogen atom, a halogen atom, a hydrocarbon group having from 1 to 20 carbon atoms and optionally having a substituent, or an aromatic heterocyclic group having from 2 to 20 carbon atoms and optionally having a substituent.