The improvement in hole-transporting and electroluminescent properties of diketopyrrolopyrrole pigment by grafting with carbazole dendrons

Abstract

Diketopyrrolopyrrole (DPP) pigments are essential and have been intensively exploited as building-blocks for the synthesis of organic semiconducting polymers and small molecules; however, DPP derivatives as emissive materials for electroluminescent (EL) devices have rarely been explored. In this work, a series of new DPP derivatives grafted with carbazole dendrons in a non-conjugated fashion using an amide linkage was designed to improve the performance of DPP in EL devices. Three DPP derivatives (G0DPP, G1DPP and G2DPP) bearing di(p-chlorophenyl)-DPP (Pigment Red 254) as the core substituted with a hexyl chain, N-hexyl carbazole and N-hexyl-N′-9,3′:6′,N′′-tercarbazole, respectively, were synthesized to afford improved hole-transporting properties without affecting the photophysical and electronic properties of the DPP core. The synthesized DPP derivatives displayed an intense yellow fluorescence emission peaked at 536 nm with an absolute photoluminescence quantum yield close to unity in solution. The hole-transporting capability of molecules was improved when carbazole dendrons were incorporated, which increased with an increase in the generation of substituent carbazole dendrons in the order of G0DPP < G1DPP < G2DPP. Significantly, the use of G2DPP, showing the highest hole mobility, in an EL device yielded a strong and stable yellow emission peaked at 556 nm (CIE x, y color coordinates of (0.45, 0.53)) with a brightness of 3060 cd m⁻², maximum luminous efficiency of 9.24 cd A⁻¹ and a maximum EQE of 3.11%.