Method for the production of monomers useful in the manufacture of semiconductive polymers

1. A method of forming a compound of formula (IV):

said method comprising the steps of:

a) reacting a compound of formula (I) with a compound of formula S 1 -M to give a compound of formula (II);

b) reacting the compound of formula (II) with a compound of formula S 2 -M to give a compound of formula (III); and

c) eliminating H 2 X from the compound of formula (III) to give a compound of formula (IV),

wherein

Ar 1 and Ar 2 are independently selected from optionally substituted aryl or heteroaryl groups;

X is O, S, NH or NR;

L is a bond or a linking group which contains 1, 2 or 3 atoms;

R and R 1 are independently selected from the group consisting of optionally substituted alkyl, aryl, alkylaryl, arylalkyl and heteroaryl groups;

R 2 is selected from the group consisting of alkoxy, aryloxy, arylalkyloxy, alkylaryloxy, alkylthio, arylthio, alkylarylthio and arylalkylthio;

H is bound to a carbon atom C′ of Ar 2 ;

C′ and the carbon atom of C═X are separated by 3-5 atoms;

S 1 and S 2 are each selected from optionally substituted alkyl, aryl or heteroaryl groups, M comprises a metal; and

M is linked to S 1 and S 2 by a carbon-metal bond.

2. A method according to claim 1 wherein alkyl is C 1 -C 20 -alkyl, arylalkyl is C 7 -C 20 -arylalkyl, alkylaryl is C 7 -C 20 -alkylaryl, aryl is C 6 -C 20 -aryl, heteroaryl is C 5 -C 20 -heteroaryl, alkoxy is C 1 -C 20 -alkoxy, aryloxy is C 6 -C 20 -Aryloxy, arylalkyloxy is C 7 -C 20 -arylalkyloxy, alkylaryloxy is C 7 -C 20 -alkylaryloxy, alkylthio is C 1 -C 20 -alkylthio, arylthio is C 6 -C 20 -arylthio, alkylarylthio is C 7 -C 20 -alkylarylthio, arylalkylthio is C 7 -C 20 -arylalkylthio.

3. A method according to claim 1 wherein Ar 1 and Ar 2 are phenyl or substituted phenyl.

4. A method according to claim 1 , wherein X is O or S.

5. A method according to claim 1 , wherein L is a bond.

6. A method according to claim 1 , wherein R is C1-10 alkyl.

7. A method according to claim 1 , wherein R 1 is C1-10 alkyl.

8. A method according to claim 1 , wherein R 2 is C1-10 alkoxy.

9. A method according to claim 1 , wherein M is lithium, zinc or Mg-Hal wherein Hal is a halide.

10. A method according to claim 1 , wherein S 1 and S 2 are independently selected from optionally substituted aryl or alkyl.

11. A method according to claim 1 , wherein S 1 and S 2 are independently selected from optionally substituted aryl or alkyl and S 1 and S 2 are different from each other.

12. A method according to claim 1 , wherein Ar 1 and Ar 2 of the compound of formula (I) are each substituted with a polymerisable group P.

13. A method according to claim 1 , comprising the further step of providing each of Ar 1 and Ar 2 of the compound of formula (II), (III) or (IV) with a polymerisable group P.

14. A method according to claim 12 , wherein each polymerisable group P is independently a halide or a boron derivative group selected from a boronic acid group, a boronic ester group and a borane group; or a moiety of formula —O—SO 2 -Z wherein Z is selected from the group consisting of optionally substituted alkyl and aryl.

15. A method according to claim 12 wherein each polymerisable group P is independently a leaving group capable of participating in a polycondensation reaction.

16. A method according to claim 1 wherein

Ar 1 and Ar 2 are phenyl or substituted phenyl,

X is O or S,

L is a bond,

R is C1-10 alkyl,

R 1 is C1-10 alkyl,

R 2 is C1-10 alkoxy,

M is lithium, zinc or Mg-Hal wherein Hal is a halide,

S 1 and S 2 are independently selected from optionally substituted aryl or alkyl and S 1 and S 2 are are different from each other.