Four A-π-D-π-A type small organic molecules with 1,8-naphthalimide motifs were successfully synthesised. The designed compounds are built of two 1,8-naphthalimide units linked via ethynyl π-linkages with selected functionalised donor motifs i. e. 2,2'-bithiophene, fluorene, phenothiazine and carbazole derivative. The synthesis based on Sonogashira cross-coupling allowed us to obtain the presented dyes with good yields. The resulting symmetrical small molecules' optical, electrochemical and thermal properties were thoroughly investigated, and their potential applicability for the OLED devices was demonstrated. In addition, the relationship between molecular structure and properties was considered by employing experimental and theoretical studies. As a result of using various donor groups, it was possible to achieve efficient electroluminescence in the range from green (DEV4) to orange-red light (DEV3) with a maximum luminance of 3 820 cd/m2 for DEV4. Upon the insertion of an acetylene linker to the designed molecules, the free rotation of D and A fragments, and hence the effective π-electron communication within the entire molecule, is possible, which was confirmed by DFT studies. The obtained dyes are characterised by high thermal stability, reversible oxidation-reduction process, satisfactory optoelectronic properties and good solubility in organic solvents, which is advisable for the application in small molecular organic light-emitting diodes (SM-OLEDs) technology.
Keywords: 1,8-naphthalimide; SM-OLED; acetylene linkage; cross-coupling; donor-acceptor systems.
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