Carbazole-Based Materials for Organic Thin-Film Transistors and Organic Light-Emitting Diodes
This thesis deals with the preparation and characterization of novel organic semiconductors based on the carbazole heterocycle for electronic and optoelectronic applications, specifically to be studied as active layers in OTFTs and as emitting layers in OLEDs. Carbazole-based materials are recognise...
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| Tipo de recurso: | tesis doctoral |
| Estado: | Versión publicada |
| Fecha de publicación: | 2017 |
| País: | España |
| Institución: | CBUC, CESCA |
| Repositorio: | TDR. Tesis Doctorales en Red |
| OAI Identifier: | oai:www.tdx.cat:10803/404560 |
| Acceso en línea: | http://hdl.handle.net/10803/404560 |
| Access Level: | acceso abierto |
| Palabra clave: | Semiconductors orgànics Semiconductores orgánicos Organic semiconductors Ciències Experimentals i Matemàtiques 547 |
| Sumario: | This thesis deals with the preparation and characterization of novel organic semiconductors based on the carbazole heterocycle for electronic and optoelectronic applications, specifically to be studied as active layers in OTFTs and as emitting layers in OLEDs. Carbazole-based materials are recognised for their high thermal stability, high emission efficiencies and excellent hole-transporting properties associated to its electron-donating ability, which make of them promising candidates for OTFTs and OLEDs applications. OLEDs have been studied extensively due to their promising applications in flat panel displays and solid-state lighting. However, further improvement of power efficiency and colour purity are still required to produce more efficient industrial devices. Thus, the first part of this thesis deals with the preparation of a series of carbazole-based blue emitters for their application as emitting layers in blue and in particular in deep-blue OLEDs. The extension of the π-conjugated carbazole system by preparing bicarbazole and tricarbazole derivatives afforded materials with the sought deep-blue emission properties in the solid state, which were modulated by the insertion of the ethynylene linker. OLED devices exhibited very low turn-on voltages and a maximum luminance as high as 1.4 x 104 cd m–2. The second part of this thesis is focused on the development of new organic semiconductors with effective charge transport properties. In order to obtain new n-type or ambipolar materials, the hole-transporting behaviour of the electron-donating carbazole moiety was modified by the introduction of electron-withdrawing groups on its structure. As a first approach, the coupling of the carbazole heterocycle with the electron acceptor tris(2,4,6-trichlorophenyl)methyl radical (TTM) yielded ambipolar materials, whose charge-transporting properties were found to be dependent on the substitution patterns of the carbazole core. As a second approach, the introduction of the strong electron-withdrawing tricyanovinyl group on the carbazole core afforded a push-pull system with high electron affinity, resulting in materials with n-type or ambipolar behaviour as determined by TOF and OTFT measurements. The last part of this thesis is focused on the preparation of a series of p-type carbazole related derivatives, in which the extension of the π-conjugated core was progressively varied in order to study its effect on the charge-transporting properties. Indolo[3,2-b]carbazole and triindole derivatives showed enhanced OTFT device performance with hole mobilities in the range of 10–3 to 0.1 cm2 V–1 s–1. In particular, N-trimethyltriindole exhibits a face-to-face molecular packing with π–π interactions, and an optimal perpendicular molecular disposition to the substrate surface as determined by XRD, that can be related to a more favourable charge transport in the OTFT devices. The introduction of long hexyl chains in the triindole core contributes with additional C–H···π interactions to those of π–π type between the triindole cores, enhancing the degree of molecular order in the thin films as reflected in the determined hole mobility, which was found to be the highest value of all the series with a value of 0.1 cm2 V–1 s–1. The knowledge of the molecular packing and intermolecular interactions in the organic layers has been proved to be essential to rationalize the charge-transporting properties and it is shown here to be a useful tool to be considered on the design of new organic semiconductors. |
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