Polycyclic dithiophenes

A compound of the formula:

• wherein
• R1 and R1′ independently of each other are H or a substituent, halogen or SiR6R4R5;
• R2 and R2′ may be the same or different and are selected from C1-C25alkyl, C3-C12cycloalkyl, C2-C25alkenyl, C2-C25alkynyl, C4-C25aryl, C5-C25alkylaryl or C5-C25aralkyl, each of which is unsubstituted or substituted, and if R3 and R3′ within the definition of X together complete a ring structure, or X is a bridging group conforming to one of the formulae
• R2 and/or R2′ may also be halogen or hydrogen;
• X is a divalent linking group selected from
• Y and Y′ independently are selected from
• n and p independently range from 0 to 6;
• R3 and R3′ independently are hydrogen or a substituent, or are amino, or together, with the carbon atoms they are attached to, complete a 5- or 6-membered unsubstituted or substituted hydrocarbon ring, or a 5-membered unsubstituted or substituted heterocyclic ring comprising at least one hetero atom selected from N, O, S, where any substituent, if present, is as defined below, or one substituent on the heterocyclic ring is a moiety of the formula
• where L stands for a divalent organic linking group, such as alkylene (e.g. C2-C12), phenylene, cycloalkylene;
• A1 is a divalent moiety O, S, NR;
• or R3 and R3′ together form a bridging group
• R4, R5, R6 independently are selected from C1-C25alkyl, C3-C12cycloalkyl, C4-C25aryl, or C5-C25aralkyl;
• and the neighbouring residues R4 and R5 may further be interlinked to form a divalent hydrocarbon residue of 4 to 25 carbon atoms which may be substituted and/or interrupted;
• R7 and R7′ independently are H or a substituent;
• or vicinal R7 and R7′ together, with the carbon atoms they are attached to, complete a 5-membered unsubstituted or substituted heterocyclic ring comprising at least one hetero atom selected from N, O, S;
• R8 is substituted C4-C10aryl, C1-C19heteroaryl, or said aryl or heteroaryl attached via divalent organic linking group L as defined above;
• R9, R9′, R10 and R10′ independently are hydrogen and one or more of the neighbouring residues R9 and R9′, or R9 and R10 and/or R9′ and R10′, together, with the carbon atoms they are attached to, complete a 5-membered unsubstituted or substituted heterocyclic ring comprising at least one hetero atom selected from N, O, S;
• R23 and R23′ each is a substituent, especially alkyl, OH or alkoxy;
• any substituent, if present, is selected from halogen, OR, C1-C25alkyl, C2-C25alkenyl, C1-C25alkylthio, C1-C25acyl, C4-C10aryl, C1-C9heteroaryl, C3-C12cycloalkyl, C2-C11heterocycloalkyl, C1-C25acyloxy;
• or is selected from the residues COR, CH═NR, CH═N—OH, CH═N—OR, COOR, CONHR, CONRR′, CONH—NHR, CONH—NRR′, SO2R, SO3R, SO2NHR, SO2NRR′, SO2NH—NHR, SO2NH—NRR′, S(O)R, S(O)OR, S(O)NHR, S(O)NRR′, S(O)NH—NHR, S(O)NH—NRR′, SiRR′R″, PORR′, PO(OR)R′, PO(OR)2, PO(NHR)2, PO(NRR′)2, CN, NO2, NHR, NRR′, NH—NHR, NH—NRR′, CONROH;
• and if bonding to saturated carbon or to sulphur, may also be oxo;
• R, R′ and R″ independently are selected from C1-C25alkyl, C1-C25haloalkyl, C5-C10aryl, C3-C12cycloalkyl, preferably from C1-C6alkyl, phenyl, cyclopentyl, cyclohexyl;
• and R may also be hydrogen;
• where each substituent, or R, R′ and R″, which is C4-C10aryl or C1-C9heteroaryl, itself is unsubstituted or substituted by C1-C4alkyl, C2-C4alkenyl, C1-C4alkoxy, CHO, C1-C4alkyl-carbonyl, C2-C4alkenyl-carbonyloxy, allyloxy, halogen, and any neighbouring substituents may be linked together by a carbon-carbon single bond or double bond.