Preparation of pi-extended naphthalene diimides and their use as semiconductor

A compound of the formula (1) or (2)

• wherein
• X is O or NR13,
• wherein R13 is H, C1-30-alkyl, C3-8-cycloalkyl, C6-14-aryl or a 5 to 14 membered heterocyclic system A,
• R1, R2, R7 and R8 are independently from each other H, C1-30-alkyl, C3-8-cycloalkyl, C6-14-aryl or a 5 to 14 membered heterocyclic system A, and
• R3, R4, R5, R6, R9, R10, R11 and R12 are independently from each other H, C1-30-alkyl, C3-8-cycloalkyl, C6-14-aryl, a 5 to 14 membered heterocyclic system A, halogen, NR14R15, OH, OR16, SH, SR17, CN, NO2, —S—CN, —C(O)—H, —C(O)—R18, COOH, —C(O)—NR19R20, —SO2—OH, —SO2—NH2 or —SO2—R21, wherein
• R14, R15, R16, R17, R18, R19, R20 and R21 are independently from each other H, C1-30-alkyl, C3-8-cycloalkyl, C6-14-aryl or a 5 to 14 membered heterocyclic system A,
• or
• R3 and R4,
• R5 and R6,
• R9 and R10, or
• R11 and R12
• together with the C-atoms, to which they are attached, form a C5-14-membered ring system or a 5 to 14 membered heterocyclic system B,
• wherein
• C1-30-alkyl is optionally substituted with one or more substituents selected from the group consisting of —O—C1-10-alkyl, —[—O—C1-6-alkylene-]n-O—C1-10-alkyl, phenyl, cyclopentyl, cyclohexyl, halogen, —C(O)O—R22, —O—C(O)—R23 and C(O)—R24,
• C3-8-cycloalkyl is optionally substituted with one or more substituents selected from the group consisting of C1-10-alkyl, —O—C1-10-alkyl, —[—O—C1-6-alkylene-]n-O—C1-10-alkyl and phenyl,
• C6-14-aryl, the C5-14-membered ring system, the 5 to 14 membered heterocyclic system A and the 5 to 14 membered heterocyclic system B is optionally substituted with one or more substituents selected from the group consisting of C1-10-alkyl, —O—C1-10-alkyl, —[—O—C1-6-alkylene-]n-O—C1-10-alkyl, cyclopentyl, cyclohexyl, phenyl, halogen, CN, NO2, —S—CN, —C(O)—H, —C(O)O—R22, —O—C(O)—R23 and C(O)—R24,
• wherein
• C1-10-alkyl is optionally substituted with one or more halogen,
• R22, R23 and R24 are independently from each other C1-10-alkyl, cyclopentyl, cyclohexyl or phenyl, and
• n is 1 to 15.