Stable organic blue-light-emitting devices prepared from poly[spiro(fluorene-9,9'-xanthene)]

Abstract

A short, efficient synthetic route has been developed for the preparation of 2,7-dibromospiro-[fluorene-9,9'-(2',7'-di-n-octyloxyxanthene)], which was subsequently polymerized with the corresponding diborolane through Suzuki coupling to afford a fluorene-based homopolymer, PSFX, that contains a spiroxanthene group functionalized on the C-9 position of each fluorene repeat unit. Single-crystal X-ray diffraction analysis of the dibromo monomer revealed that the spiro-fused fluorene and xanthene moieties lie perpendicular to one another. As a consequence of the incorporation of the spiro pendant group, PSFX possesses a high glass transition temperature and good thermal stability while displaying its stable blue emission in the solid state. A light-emitting diode device prepared using PSFX as the emitting layer exhibits an efficient, stable blue emission; it has a turn-on voltage of 6 V and a maximum external quantum efficiency of 1.74% ph/el. Even when the brightness was increased up to 10(3) cd/m(2) (ca. 11 V), the CIE color coordinates of the resulting EL spectrum remained in the deep-blue region (0.15, 0.07) and the device's efficiency was 1.33% ph/el.