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高電荷傳輸性質有機半導體分子之設計、合成及在有機電子元件應用

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The polyheteroaromatics (PHs), including electron-rich polycyclic frameworks, display interesting set of properties such as optical, emissive, HOMO‒LUMO energy levels and others. Besides these properties, the packing motif within a crystal is another essential feature which influences the electroni

c coupling between neighbouring molecules. Correlation between chemical structures of PH systems with their properties including packing motifs, electronic coupling, and charge carrier mobility is always interesting and important. This perspective is crucial for the designing of new PH systems for m

any applications including organic electronics. For example, the electronic structure and molecular shape of PH molecules will determine the packing mode as cofacial, herringbone, lamellar, brick wall and other styles. These packing motifs relate to the electronic coupling, which is crucial to charg

e transporting. Contorted molecules have a high tendency to give cofacial-packing motif, and possibly high electronic coupling. In this regard, we are interested in contorted PHs involving thiophene unit. In particular, the design, synthesis, and characterizations of new thiophene-based contorted P

Hs as well as their potentials in field-effect transistor application and as hole transporting layers in perovskite solar cells. Furthermore, we are interested in embedding diacetylene units to the thiophene-based semiconductor BTBT, in order to prepare polydiacetylenes attached with crystalline BTB

T for possible used in FET applications.The two series of contorted, thiophene-based PHs are diphenanthro[9,10-b:9',10'-d]thiophene (DPT) and benzo[3,4]phenanthro[1,2-b]benzo[3,4]phenanthro[2,1-d]thiophene (BPBPT), both with polyarylthiophenes, as the central key precursors. The interesting part of

this conversion was regioselective Scholl reactions, which selectively led to the desired DPT and BPBPT frameworks. NMR, high-resolution mass, techniques were used to characterize these phenathrothiophene and benzophenanthrothiophenes, while also the structural evidence for the proposed annulating p

atterns of DPT and BPBPTs came for the single-crystal analyses of the derivatives. The molecular structures of these DPTs and BPBPTs, as revealed by single-crystals X-ray analyses, include many fjords, which possibly allow these PHs to assemble in cofacial packing motifs. Single crystal-based transi

stors based on selected DPTs and BPBPTs single-crystals were fabricated and revealed that these materials are p-channel carriers. The best SCFET performance was measured from the single-crystals of benzophenathrothiophene, Flu-BPBPT, giving the highest mobility of 2.03 cm2V-1s-1,For the synthesis of

BPBT-cored diacetylenes, they were prepared from 2-alkyneBTBT with 1-bromoalkyne, using copper-catalyzed Sonogashira coupling reaction. The chemical structures of BTBT-diacetylenes were confirmed by NMR, and high-resolution mass analyses, along with photophysical measurements. These derivatives wer

e subjected to UV-irradiation, with the idea that diacetylene units at the BTBT cores can undergo topochemical polymerization reactions to give conjugated polymer. The results showed that depend on the location of the diacetylene in the chain, an odd-even effect was observed.On the other side, two d

onor–π–donor type (D–π–D) DPT derivatives with diphenanthrothiophene (DPT) as the central core carrying peripheral arylamino substituents, were synthesized using Suzuki coupling reactions between dibromo DPTs and triaryl amine boronate esters. Essential functional properties such as optical, thermal

, energy level alignments, film morphologies, hole extraction ability, hole mobility and photovoltaic performance were measured showing the suitability of these two DPTs for PSC application. The best performance, with high power conversion efficiency (PCE) of 19.3%, was measured from a PSC device wi

th the material as hole-transporting layer. This PCE value is higher than that obtained from the bench-mark HTM of Spiro-OMeTAD (PCE = 18.14%).