Short Alkyl Chain Engineering Modulation on Naphthalene Flanked Diketopyrrolopyrrole toward High‐Performance Single Crystal Transistors and Organic Thin Film Displays

Abstract

Studying multi‐purpose applications of a specific material is a challenging topic in the organic electronics community. In this work, through molecular engineering and smart device structure design strategy, high performance in transistors and thin film display devices is simultaneously achieved by applying a simple new dye molecule, naphthalene flanked diketopyrrolopyrrole (DPPN), as the active layer material. Short alkyl chains (hexyl or octyl side groups for H‐DPPN and O‐DPPN, respectively) are adapted to improve the hole mobility in organic thin film transistors (OTFTs) and single crystal transistors (SCTs). Specifically, H‐DPPN shows a similar hole mobility in either OTFTs or SCTs, while O‐DPPN exhibits a dramatically enhanced mobility, reaching 0.125 cm2 V−1 s−1 in SCTs. Additionally, a smart organic light emitting diode (OLED) device is designed by using DPPN molecule as the dopant with a host matrix. The promising external quantum efficiencies of 4.0% and 2.3% are achieved for H‐DPPN and O‐DPPN fabricated OLEDs. Overall, in this work, it is reported that DPP‐based small molecules can simultaneously function well in both transistors and thin film displays with high device performance through molecular and smart device engineering.

Synthesis and electronic properties of nitrogen-doped π-extended polycyclic aromatic dicarboximides with multiple redox processes

“…This behavior is characteristic of a stronger molecular interaction in the aggregated state, 46 as we previously observed for naft-2 in solution. In agreement with that observed for other alkyl substituted π-conjugated systems, 47,48 the shorter the side chains, the stronger the aggregation. Concerning naft-3, π-π-interactions are significantly decreased due to the bulky steric hindrance of the diisopropylphenyl substituent and therefore, no significant differences are found between the solution and thin film UV-Vis absorption spectra.…”

Modeling of plasmonic properties of nanostructures for next generation solar cells and beyond

“…(2.2.2)) needed to reach the plasmonic peak rapidly balloons beyond feasibility, in particular, due to a high density of states in larger systems. Such calculations are still infeasible even with TD-DFTB where thousands of excited states can routinely be included [76]. However, more than tens of thousands excitations would have to be included for NPs of more than a few nm.…”

“…To model directly NPs of dozens of nm, models with many thousands of atoms are required which is impractical. Additional complications arise when computing spectra: linear response (Casida) TD-DFT [73,74] which is widely used in smaller-scale applications, is best suited for systems with a bandgap (non-metallic) and also becomes impractical even with a few nm due to the rapid explosion of the number of excitations that have to be included to compute the spectrum through the plasmonic peak [75,76]. For this reason, real-time TD-DFT [77] has found wider use in plasmonics but still suffers from the high cost of Kohn-Sham DFT.…”

Naphthalene Flanked Diketopyrrolopyrrole: A New Functional Dye Based Optical Sensors for Monitoring Cyanide Ions in Water

“…[50] Naphthalene Flanked Diketopyrrolopyrrole dyes have been hardly reported in four papers with application as OFET devices and biosensor. [50][51][52][53] Combining a highly electron-deficient tert-butyl carbonate group and naphthalene flanked diketopyrrolopyrrole (DPPN) as chromophore offers an ideal site for cyanohydrin forming reaction. In the present work, we have designed and synthesized a novel naphthalene flanked diketopyrrolopyrrole dye with specific alkyl engineering substituents, namely, ditert-butyl 3,6-di(naphthalene-2-yl)-1,4-dioxopyrrolo [3,4-c]pyrrole-2,5(1H,4H)-dicarboxylate (TBC-DPPN) for CN − dual detection by UV-Vis and fluorescence spectroscopy.…”