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Light-Emitting Porphyrin Derivative Obtained From a Subproduct of the Cashew Nut Shell Liquid: A Promising Material for OLED Applications

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Light-Emitting Porphyrin Derivative Obtained From a Subproduct of the Cashew Nut Shell Liquid: A Promising Material for OLED Applications

Nayane Maria de Amorim Lima et al. Materials (Basel).

Abstract

In this work, the meso-tetra[4-(2-(3-n-pentadecylphenoxy)ethoxy]phenylporphyrin (H₂P), obtained from the cashew nut shell liquid (CNSL), and its zinc (ZnP) and copper (CuP) metallic complexes, were applied as emitting layers in organic light emitting diodes (OLEDs). These compounds were characterized via optical and electrochemical analysis and the electroluminescent properties of the device have been studied. We performed a cyclic voltammetry analysis to determine the Highest Occupied Molecular Orbital (HOMO) and Lowest Unoccupied Molecular Orbital (LUMO) energy levels for the porphyrins, in order to select the proper materials to assemble the device. H₂P and ZnP presented fluorescence emission band in the red region, from 601 nm to 718 nm. Moreover, we verified that the introduction of bulky substituents hinders the π⁻π stacking, favoring the emission in the film. In addition, the strongest emitter, ZnP, presented a threshold voltage of 4 V and the maximum irradiance of 10 μW cm-2 with a current density (J) of 15 mA cm-2 at 10 V. The CuP complex showed to be a favorable material for the design of OLEDs in the infrared. These results suggest that the porphyrins derived from a renewable source, such as CNSL, is a promising material to be used in organic optoelectronic devices such as OLEDs.

Keywords: OLEDs; cashew nut shell liquid; electroluminescence; photoluminescence; porphyrins.

Conflict of interest statement

The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
Synthesis of porphyrin H2P from cardanol.
Scheme 2
Scheme 2
Synthesis of metalloporphyrins.
Figure 1
Figure 1
(a) UV-Vis absorption spectra of H2P, CuP, and ZnP in CH2Cl2, and in (b) solid state.
Figure 2
Figure 2
Photoluminescence spectra of H2P and ZnP excited at 421 nm in CH2Cl2 at 10−6 M (a), and normalized spectra of the solid state of H2P and ZnP (b).
Figure 3
Figure 3
Emission spectra of H2P in different concentrations.
Figure 4
Figure 4
Photoluminescence of CuP in film (λexc = 435 nm).
Figure 5
Figure 5
Schematic structure of the OLEDs.
Figure 6
Figure 6
Energy level diagram of the OLEDs.
Figure 7
Figure 7
Electroluminescence spectra and the irradiance and current density curves for the devices OLED-1 (H2P), OLED-2 (ZnP), and OLED-3 (CuP).

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