Pyrrolopyrrole derivatives, their manufacture and use as semiconductors

A compound of formula (I)

• wherein R1 and R2 are independently selected from the group consisting of:
• hydrogen;
• a C1-C100 alkyl group;
• —COOR103;
• a C1-C100 alkyl group that is substituted by one or more halogen atoms, a hydroxyl group, a nitro group, —CN, or a C6-C24 aryl group;
• a C1-C100 alkyl group that is interrupted by —O—, —COO—, —OCO—, or —S—;
• a C7-C100 arylalkyl group;
• a carbamoyl group;
• a C5-C12 cycloalkyl, which can be substituted one to three times with at least one selected from the group consisting of C1-C8 alkyl and C1-C8 alkoxy;
• a C6-C24 aryl group,
• and pentafluorophenyl,
• R103 is:
• H;
• C6-C24 aryl;
• C6-C24 aryl substituted by C1-C25 alkyl or C1-C25 alkoxy;
• C1-C50 alkyl;
• or C1-C50 alkyl interrupted by —O—;
• a is l and d is 1,
• Ar1 and Ar4 are each independently a bivalent group of formula (II)
• wherein one of X3 and X4 is N, and
• the other of X3 and X4 is CR100 and
• R100 is hydrogen or C1-C25alkyl,
• b, c, e, f, g and h are each independently 0, 1, 2 or 3,
• Ar2, Ar3, Ar5, Ar6, Ar7 and Ar8 are as described for Ar1 or are each independently
• wherein X is SiR60R61, NR62, CR10R11, S, or O,
• p is 0, 1, or 2,
• R5 is an aliphatic hydrocarbon group comprising up to 25 carbon atoms, C1-C25 alkoxy, or two vicinal groups R5 together represent alkylene or alkenylene comprising up to 7 carbon atoms, where, when p is 2, two R5 groups are independent,
• R6, R7, R9, R12, R13, R14, R15, R16, R17, R18, R19, and R21 are each independently hydrogen, C1-C25alkyl, C1-C25alkoxy, C6-C24aryl, C7-C25aralkyl, or heteroaryl, or R6 and R7 together represent alkylene or alkenylene comprising up to 25 carbon atoms and that are both optionally bonded via at least one selected from the group consisting of oxygen and sulfur to the thienyl residue,
• R10 and R11 are each independently selected from the group consisting of hydrogen, C1-C25 alkyl, C7-C25 aralkyl, C6-C24 aryl, and 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 comprising up to 18 carbon atoms,
• b) C1-C18 alkoxy or C2-C18 alkylenedioxy, in both of which at least one carbon atom that is not adjacent to oxygen is optionally replaced by oxygen, or
• c) C6-C24 aryl, C7-C25 aralkyl, heteroaryl, C3-C12 cycloalkyl or C4-C12 cycloalkyl-alkyl;
• wherein R60 and R61 are each independently hydrogen, C1-C25 alkyl, or phenyl;
• R62 is:
• hydrogen;
• C7-C25 arylalkyl;
• C6-C24 aryl;
• C6-C24 aryl substituted by C1-C25 alkyl, C1-C25 perfluoroalkyl, or C1-C25 alkoxy;
• C1-C25 alkyl;
• C1-C25 alkyl interrupted by —O—, or —S—;
• or
• —COOR103;
• wherein R3 and R4 are each independently:
• hydrogen;
• an aliphatic hydrocarbon group comprising up to 25 carbon atoms, alkoxy or alkenyloxy comprising up to 25 carbon atoms;
• a halogen;
• a cycloaliphatic, cycloaliphatic-aliphatic, aromatic, aromatic-aliphatic, heteroaromatic or heteroaromatic-aliphatic group comprising up to 25 carbon atoms;
• wherein w is 0 or 1,
• BU is a bridging unit, and
• A3 and A3′ are each independently a C6-C24 aryl group, or a C2-C26 heteroaryl group, which are optionally substituted,
• and wherein either
• R22 to R58 are each independently
• hydrogen,
• an aliphatic hydrocarbon group comprising up to 25 carbon atoms,
• an alkoxy comprising up to 25 carbon atoms,
• an alkenyloxy comprising up to 25 carbon atoms,
• a halogen,
• or a cycloaliphatic, cycloaliphatic-aliphatic, aromatic, aromatic-aliphatic, heteroaromatic or heteroaromatic-aliphatic group comprising up to 25 carbon atoms, or
• R27 and R28, or R27 and R58 together represent alkylene or alkenylene comprising up to 25 carbon atoms and that are both optionally bonded via at least one selected from the group consisting of oxygen and sulfur to the thienyl residue.