Naphthalene-diimide-heterocycle-naphthalene diimide oligomers as organic semiconductors and transistors therefrom

A bis(naphthalene diimide) compound or a mixture thereof having the structure:

• wherein
• a) hAr is a heteroaryl selected from:
• wherein
• i) “a” is an integer 1, 2, 3, or 4;
• ii) each X and X′ is independently selected from O, S, Se, or NR6, wherein R6 is a C1-C30 organic group independently selected from normal, branched, or cyclic alkyl, fluoroalkyl, aryl, heteroaryl, alkyl-aryl, and alkyl-heteroaryl groups optionally substituted with one or more fluoro, cyano, alkyl, alkoxy groups;
• iii) each Y, Y′, Y″ and Y′″ is independently selected from N, and CR7, where R7 is hydrogen, fluoro, or a C1-C30 organic group independently selected from cyano, normal, branched, or cyclic alkyl, perfluoroalkyl, alkoxy, perfluoroalkoxy, aryl, heteroaryl, alkyl-aryl, and alkyl-heteroaryl groups, optionally substituted with one or more fluoride, cyano, alkyl, alkoxy groups;
• iv) each Z and Z′ is independently selected from O, S, Se, C(R8)2, Si(R8)2, NR8, (CO), (CO)2 or C═C(CN)2, wherein R8 is a C1-C30 organic group independently selected from normal, branched, or cyclic alkyl, perfluoroalkyl, aryl, heteroaryl, alkyl-aryl, and alkyl-heteroaryl groups, optionally substituted with one or more fluoro, cyano, alkyl, alkoxy groups;
• b) each R1 and R1′is a C1-C30 organic group independently selected from a normal, branched, or cyclic alkyl, aryl, heteroaryl, alkyl-aryl, or alkyl-heteroaryl group optionally substituted with one or more halide, cyano, alkyl, or alkoxy groups;
• c) R2, R3, and R4 are independently selected from hydrogen, halide, or a C1-C30 organic group independently selected from cyano, normal, branched, or cyclic alkyl, fluoroalkyl, aryl, heteroaryl, alkyl-aryl, acyl- and alkyl-heteroaryl groups, optionally substituted with one or more fluoro, cyano, alkyl, alkoxy groups.