Process for the preparation of tetracarboxynaphthalenediimide compounds disubstituted with heteroaryl groups

摘要

A process for the preparation of a tetracarboxynaphthalenediimide compound disubstituted with heteroaryl groups having general formula (I), comprising the reaction of at least one disubstituted N,N′-dialkyl-1,5,8-tetracarboxynaphthalenediimide with at least one heteroaryl compound. Said tetracarboxynaphthalenediimide compound disubstituted with heteroaryl groups can be advantageously used as monomer in the synthesis of semiconductor polymers which can be advantageously used in the construction of organic field effect transistors (OFET) or of organic thin film transistors (OTFT).

主权项

1. A process for preparing a tetracarboxynaphthalenediimide compound disubstituted with heteroaryl groups of formula (I):the process comprising:
reacting at least one disubstituted N,N′-dialkyl-1,4,5,8-tetracarboxy-naphthalenediimide of formula (II):with at least one heteroaryl compound of formula (III): wherein, in formulae (I)-(III),
R1 represents a C1-C30 alkyl group;Y represents an oxygen atom; a sulfur atom; a NR5 group where R5 represents a hydrogen atom; or a C1-C20 alkyl group;Z represents a nitrogen atom; or a CR2 group where R2 is defined below;R3 represents a hydrogen atom; a linear or branched C1-C20 alkyl group; an optionally substituted cycloalkyl group; an optionally substituted aryl group; a linear or branched C1-C20 alkoxyl group; a polyethyleneoxyl group R1—O—[—CH2—CH2—O]n— where R1 is defined above and n is an integer of from 1 to 4; a —R6—OH group where R6 represents a linear or branched C1-C20 alkylene group; a —R6—OR7 group where R6 is defined above and R7 represents a linear or branched C1-C20 alkyl group, or a polyethyleneoxyl group R1—O—[—CH2—CH2—O]n— where R1 is defined above and n is an integer of from 1 to 4; a —COR1 group where R1 is defined above; a —COOR1 group where R1 is defined above; a —CHO group; or a cyano group (—CN);R2 represents a hydrogen atom; a linear or branched C1-C20 alkyl group; or, when R3 is different from hydrogen or when R3=R2, R2 represents a linear or branched C1-C20 alkoxyl group;or R3 and R2 are optionally bound to each other so as to form, together with the carbon atoms to which R3 and R2 are bound, a cycle or polycyclic system containing from 3 to 14 carbon atoms, saturated, unsaturated, or aromatic, optionally containing one or more heteroatoms which are optionally oxygen, sulfur, nitrogen, silicon, phosphorous, and selenium;R4 represents a hydrogen atom; a linear or branched C1-C20 alkyl group; an optionally substituted cycloalkyl group; an optionally substituted aryl group; an optionally substituted heteroaryl group; a —CHO group; a —COR1 group where R1 is defined above; a —COOR1 group where R1 is defined above; a —CONR2 group where R2 is defined above; or a cyano group (—CN);or R2 and R4 are optionally bound to each other so as to form, together with the carbon atoms to which R2 and R4 are bound, a cycle or polycyclic system containing from 3 to 14 carbon atoms, saturated, unsaturated, or aromatic, optionally containing one or more heteroatoms which are optionally oxygen, sulfur, nitrogen, silicon, phosphorous, and selenium; and X represents a halogen atom selected from the group consisting of chlorine, bromine, and iodine.