Heterocyclic fluorescent dyes and method of production thereof

摘要

The invention relates to novel compounds of formula (III) that can be used as heterocyclic dyes of unique structure and properties. These compounds can be obtained in a three-step synthesis from simple substrates. The compounds according to the invention have excellent solubility in organic solvents and excellent film-forming properties. In addition, high efficiency of energy conversion, excellent field-effect mobility, good on/off current ratios and/or excellent stability can be observed, when the compounds according to the invention are used in organic field effect transistors, organic photovoltaics (solar cells) and photodiodes.;

主权项

1. A compound of formula (III):wherein
Ar denotes a homo- or heteroaromatic system, which may be substituted, or unsubstituted; and R13, R13′, R14 and R14′ are independently of each other hydrogen, C1-C25alkyl, C2-C25alkenyl, C2-C25alkenyl, which may optionally be interrupted by one or more oxygen or sulphur atoms and/or is optionally substituted by a group ESi or one or more halogen atoms; C2-C25alkinyl, C3-C12cycloalkyl, C3-C12cycloalkyl-alkyl, which may optionally be interrupted by one or more oxygen or sulphur atoms and/or is optionally substituted by a group ESi or one or more halogen atoms; C7-C25arylalkyl, C7-C25arylalkyl which may optionally be interrupted by one or more oxygen or sulphur atoms and/or is optionally substituted by a group ESi or one or more halogen atoms; C6-C18aryl; C6-C18aryl which is substituted by halogen, C1-C18alkyl, or C1-C18alkoxy, or C1-C25alkyl, which may optionally be interrupted by one or more oxygen or sulphur atoms and/or is optionally substituted by one or more halogen atoms; C3-C10heteroaryl; C3-C10heteroaryl, which is substituted by halogen, C1-C18alkyl, or C1-C18alkoxy; or C1-C25alkyl, which may optionally be interrupted by a group DSi, or one or more oxygen or sulphur atoms and/or is optionally substituted by one or more halogen atoms; ESi is —SiR161R162R163 or —O—SiR161R162R163; DSi is —SiR161R162—, —SiR161R162—(O—SiR161R162)d— or —O—SiR161R162—; R161, R162 and R163 are independently of each other hydrogen, C1-C25alkyl, C3-C12cycloalkyl, which might optionally be substituted with C1-C4alkyl; C1-C25haloalkyl, C2-C25alkenyl, —O—SiR164R165R166, —(O—SiR164R165)d—R166, C1-C25alkoxy, C3-C24(hetero)aryloxy, NR167R168, halogen, C1-C25acyloxy, phenyl, phenyl, which is substituted 1 to 3 times by C1-C25alkyl, halogen, cyano or C1-C25alkoxy; R164, R165 and R166 are independently of each other hydrogen, C1-C25alkyl, C3-C12cycloalkyl, which might optionally be substituted with C1-C4alkyl; C1-C25haloalkyl, C2-C25alkenyl, —O—SiR169R170R171, —(O—SiR169R170)d—R171, C1-C25alkoxy, C3-C24(hetero)aryloxy, NR167R168, halogen, C1-C25acyloxy, phenyl, phenyl which is substituted 1 to 3 times by C1-C25alkyl, halogen, cyano or C1-C25alkoxy; R169, R170 and R171 are independently of each other hydrogen, C1-C25alkyl, C3-C12cycloalkyl, which might optionally be substituted with C1-C4alkyl; C1-C25haloalkyl, C2-C25alkenyl, —O—Si(CH3)3, C1-C25alkoxy, C3-C24(hetero)aryloxy, NR167R168, halogen, C1-C25acyloxy, phenyl, phenyl, which is substituted 1 to 3 times by C1-C25alkyl, halogen, cyano or C1-C25alkoxy; R167 and R168 are independently of each other hydrogen, C6-C18aryl; C6-C18aryl which is substituted by C1-C18alkyl, or C1-C18alkoxy; or C1-C25alkyl, which may optionally be interrupted by one or more oxygen or sulphur atoms; or C7-C25arylalkyl; d is an integer from 1 to 50; with the proviso that at least one of R13, R13′, R14 and R14′ is different from hydrogen.