Pyrrolopyrrole derivatives, their manufacture and use

A semiconductor device comprising as a semiconducting effective means a compound of the formula I

• wherein R1 and R2 are independently of each other an aliphatic group having 7 to 25 carbon atoms, or a cycloaliphatic, cycloaliphatic-aliphatic, aromatic, aromatic aliphatic, heteroaromatic or heteroaromatic-aliphatic group having up to 25 carbon atoms,
• a and d independently of each other are 0, 1, 2 or 3,
• Ar1 and Ar4 are independently of each other a bivalent group of the formula II or IV
• wherein
• R6 and R7 are as defined below,
• p represents 0, 1, or 2,
• R5 is an aliphatic hydrocarbon group having up to 25 carbon atoms, or two vicinal groups R5 together represent alkylene or alkenylene having up to 7 carbon atoms, it being possible that two groups R5 present in the group of formula II differ from each other,
• b and e independently of each other represent 1, 2 or 3,
• c and f independently of each other represent 0, 1, 2 or 3,
• Ar2, Ar3, Ar5, and Ar6 are independently of each other a bivalent group of one of the formulae IV to X and L,
• wherein R6, R7, R8, R9, R12, R13, R15, R16, R17, R18, R19, R20 and R21 are independently of each other hydrogen, C1-C25alkyl, C1-C18alkoxy, C6-C24aryl, C7-C25aralkyl, or heteroaryl, or R6 and R7 together represent alkylene or alkenylene which may be both bonded via oxygen and/or sulfur to the thienyl residue and which may both have up to 25 carbon atoms,
• R10 and R11 are independently of each other hydrogen, C1-C18alkyl, C6-C24aryl, heteroaryl, or R10 and R11 together represent oxo or form a five or six membered ring, which is unsubstituted or substituted by
• a) an aliphatic hydrocarbon group having up to 18 carbon atoms,
• b) C1-C18alkoxy or C2-C18alkylenedioxy in both of which carbon atoms which are not adjacent to oxygen may be replaced by oxygen, or
• c) C6-C24aryl, C7-C25aralkyl, heteroaryl, C3-C12cycloalkyl or C4-C12cycloalkyl-alkyl, and R3 and R4 are independently of each other a group of one of the formulae XI to XIX,
• wherein R22 to R26 and R29 to R58 represent independently of each other hydrogen, an aliphatic hydrocarbon group having up to 25 carbon atoms, alkoxy or alkenyloxy having up to 18 carbon atoms, halogen, a cycloaliphatic, cycloaliphatic-aliphatic, aromatic, aromatic-aliphatic, heteroaromatic or heteroaromatic-aliphatic group having up to 25 carbon atoms, or a group of the formula (III)
• wherein R represents an aliphatic hydrocarbon group having up to 12 carbon atoms, or two groups R22 to R26 and R29 to R57 which are in the neighborhood of each other, together represent alkylene or alkenylene having up to 8 carbon atoms, thereby forming a ring, and R27 and R28 are independently of each other hydrogen, C1-C25alkyl, C1-C18alkoxy, C6-C24aryl, C7-C25aralkyl, heteroaryl, or a group of the formula (III) shown above, wherein R represents an aliphatic hydrocarbon group having up to 12 carbon atoms, or R27 and R28 together or R27 and R58 together represent alkylene or alkenylene which may be both bonded via oxygen and/or sulfur to the thienyl residue and which may both have up to 25 carbon atoms.