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Optoelectronic properties of a new luminescent-synthesized organic material based on carbazole and thiophene rings for a new generation of OLEDs devices: experimental investigations and DFT modeling

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Abstract

A new deep blue-emitting organic small molecule based on carbazole and thiophene rings was chemically synthesized using a Wittig reaction. The obtained material named carbazole–thiophene and denoted Cbz(–π–Th)2 was synthesized with a yield of 89%. The chemical structure of the Cbz(–π–Th)2 molecule was first confirmed experimentally by nuclear magnetic resonance (1H and 13C) and infrared spectroscopies. The photophysical properties of the synthesized molecule were studied by optical absorption and steady-state photoluminescence spectroscopies in a diluted solution state. The obtained material absorbs essentially in the ultraviolet part and the optical band gap \(\left( {E_{{\text{g}}}^{{{\text{opt}}}} } \right)\) was estimated to be at around 2.95 eV. By varying the excitation wavelength in the UV part, a broad blue emission is obtained with a high photoluminescence quantum yield (PLQY) of ~ 0.34 in solution. In addition, the International Commission on Illumination (CIE) coordinates obtained from the fluorescence results show that the Cbz(–π–Th)2 molecule exhibits a deep blue emission with CIE coordinates at around (0.18, 0.05) (CIEy < 0.1). Else, Density Functional Theory (DFT) and it is extended Time-dependent DFT methodologies were performed to evaluate the ground and the excited state of the examined molecule. Theoretical investigation confirms first the chemical structure and allows the investigation of the structural and electronic properties of the synthesized Cbz(–π–Th)2 molecule. In the second step, the chemical structure of the synthesized material was used as a photoactive layer in a multilayer structure forming a new generation of a simulated organic light-emitting diode. DFT results show that insertion of carbon based-molecule, especially a graphene monolayer, permits to reduce the energy of the electron injection barrier (ΔEe) from the used cathode to the Cbz(–π–Th)2 active layer, which permits to enhance the performance of the designed organic devices.

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Acknowledgements

The authors acknowledge King Abdulaziz University’s High-Performance Computing Center (Aziz Supercomputer) for supporting the computational DFT calculation done in this work. The authors are grateful to Pr Chtourou Radhouane for the authorization access to the experimental analysis done in Technopark Borj Cedria (CRTEn), Tunisia.

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The authors have not disclosed any funding.

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Authors and Affiliations

  1. Synthèse asymétriques et ingénierie moléculaires des matériaux Nouveaux Pour L’électronique Organique (LR 18ES19), Faculté des Sciences de Monastir, Université de Monastir-Tunisie, 5000, Monastir, Tunisia

    Mourad Chemek, Mourad Ben Braiek, Ali Mabrouk & Alimi Kamel

  2. Chemistry Department, Faculty of Science, King Abdulaziz University, P.O Box 42805, 21589, Jeddah, Saudi Arabia

    Nuha Wazzan

  3. Laboratory Water, Membranes and Biotechnology of the Environment, CERTE, 8020, Soliman, Tunisia

    Aida Ben Mansour & Omar Hafiane

  4. Institut National de Recherche et d’Analyse Physico-chimique, Biotechpôle Sidi Thabet. Tunis, 2020, Sidi Thabet, Tunisia

    Alimi Kamel

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Contributions

All authors contributed to the present work. Material preparation and experimental analysis were performed by CM, MB, AM, OH, and KA. Theoretical analysis was performed by CM, AM, and NW. The first draft of the manuscript was written by CM and all authors commented on previous versions of the manuscript. All authors read and approved the final manuscript.

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Correspondence to Alimi Kamel.

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Chemek, M., Braiek, M.B., Mabrouk, A. et al. Optoelectronic properties of a new luminescent-synthesized organic material based on carbazole and thiophene rings for a new generation of OLEDs devices: experimental investigations and DFT modeling. J Mater Sci: Mater Electron 34, 1706 (2023). https://doi.org/10.1007/s10854-023-11068-4

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