V‐Shaped Organic Semiconductors With Solution Processability, High Mobility, and High Thermal Durability

Okamoto, Toshihiro; Mitsui, Chikahiko; Yamagishi, Masakazu; Nakahara, K.; Soeda, Junshi; Hirose, Yasuyuki; Miwa, Kenji; Sato, Hiroyasu; Yamano, Akihito; Matsushita, Tomonori; Uemura, Tomomasa; Takeya, Jun

doi:10.1002/adma.201302086

Cited by 211 publications

(170 citation statements)

References 27 publications

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“…In the 2000s, materials research for OFETs became focused on not only high mobility but also improved solubility in common organic solvents. Various soluble small-molecule p-channel and n-channel OFET materials have been proposed, such as TIPS-Pentacene, 3 C 8 -BTBT, 4 C 10 -DNTT, 5 C 10 -DNT-VW, 6 C 10 -DNBDT 7 and PTCDI-C13, 8 as shown in Figure 1, in which the π-π interaction of the extended π-conjugate system is weakened to improve the solubility by incorporating either long alkyl chains, a bulky moiety or an asymmetric molecular shape around the molecular axis. OFETs with these crystalline films fabricated by a solution process show high FET mobilities over 1 cm 2 Vs − 1 .…”

Section: Small-molecule Ofet Materialsmentioning

confidence: 99%

Liquid crystalline organic semiconductors for organic transistor applications

Iino

Hanna

2016

Polym J

101

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The recent development of materials for organic field effect transistors (OFETs), including small-molecule and polymer materials, are briefly reviewed, and the problems that remain to be solved prior to practical application and use are discussed. Liquid crystalline materials are good candidates for OFETs because of their advantageous properties over soluble small-molecule materials. Liquid crystalline materials show good solution processability for the fabrication of uniform crystalline thin films using the precursor of uniform liquid crystalline thin films. In addition, liquid crystalline materials having their highly ordered liquid crystal phases show a high thermal durability despite their high solubility. The novel liquid crystalline material 2-phenyl-7-decyl [1]benzothieno [3,2-b][1]benzothiophene exhibits a highly ordered liquid crystal phase, the Smectic E (SmE) phase, which has good solution processability for uniform crystalline thin films by the precursor of uniform SmE thin films, shows high thermal durability and solubility, and can be used for transistor devices having a high mobility, over 10 cm 2 Vs − 1 , by thermal annealing at 120°C for 5 min. Thus, liquid crystalline materials are good semiconductor materials for organic transistor applications instead of polymer materials. INTRODUCTIONMaterials for organic field effect transistors (OFETs) have attracted considerable attention since their high mobility of over 1 cm 2 Vs − 1 , comparable to that of amorphous silicon FETs, was reported in polycrystalline thin films of pentacene fabricated by vacuum evaporation. 1 OFETs are very attractive for device applications because they can be fabricated even at room temperature to create flexible electronics on plastic substrates. Recent materials research for OFETs has been focused on soluble OFET materials because of their device applications in printed electronics. In this review, the recent development of OFET materials is briefly discussed, including the use of small molecules and polymers, and the remaining problems to be solved for their practical applications are discussed. Then, a new candidate for OFET materials, that is, liquid crystals, as a self-organizing molecular semiconductor, is discussed, focusing on how liquid crystallinity can solve the existing problems, and its high potential for OFET applications is demonstrated with a highly ordered smectic liquid crystal of 2-phenyl-7-decyl[1]benzothieno [3,2-b][1] benzothiophene (Ph-BTBT-10). 2

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Section: Small-molecule Ofet Materialsmentioning

confidence: 99%

Liquid crystalline organic semiconductors for organic transistor applications

Iino

Hanna

2016

Polym J

101

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“…We apply this analysis to organic semiconductors other than pentacene and compare the results with those of 20 The structures of these molecules are shown at the bottom of Fig. 4.…”

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confidence: 99%

Correlation between thermal fluctuation effects and phase coherence factor in carrier transport of single-crystal organic semiconductors

Fukami

Ishii

Kobayashi

et al. 2015

Applied Physics Letters

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We find that the phase coherence factor derived from Hall effect measurements of single-crystal thin-film field-effect transistors of pentacene, which relates the intrinsic charge transport with the phase coherence, has a strong correlation with the thermal fluctuations of transfer energies between neighboring molecules. This observation also holds true for other organic semiconductors such as tetracene, dianthrathiophene (DAT)-V, and dinaphtho[2,3-b:2′,3′-f]thieno[3,2-b]thiophene (DNTT). This gives us clues for constructing flexible molecular systems with high carrier mobility.

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“…The molecular and packing structures of ChDT , C 10 –ChDT , and C 10 –Th–ChDT are summarized in Figures S7–S12 (Supporting Information), Figure 3 , and Table S2 (Supporting Information). As shown in Figure 3, the ChDT unit in the C 10 –Th–ChDT molecule exhibits a bent conformation (Figure 3a, side view), which is similar to those of decyl‐substituted V‐ ( C 10 –DNT–VW ) and N‐shaped molecules ( C 10 –DNBDT–NW ) 5, 16. A dihedral angle of 7.2° was observed between the decylthienyl and the terminal thiophene moieties of the ChDT π‐core of C 10 –Th–ChDT .…”

Section: Resultsmentioning

confidence: 72%

Zigzag‐Elongated Fused π‐Electronic Core: A Molecular Design Strategy to Maximize Charge‐Carrier Mobility

et al. 2017

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Printed and flexible electronics requires solution‐processable organic semiconductors with a carrier mobility (μ) of ≈10 cm2 V−1 s−1 as well as high chemical and thermal durability. In this study, chryseno[2,1‐b:8,7‐b′]dithiophene (ChDT) and its derivatives, which have a zigzag‐elongated fused π‐electronic core (π‐core) and a peculiar highest occupied molecular orbital (HOMO) configuration, are reported as materials with conceptually new semiconducting π‐cores. ChDT and its derivatives are prepared by a versatile synthetic procedure. A comprehensive investigation reveals that the ChDT π‐core exhibits increasing structural stability in the bulk crystal phase, and that it is unaffected by a variation of the transfer integral, induced by the perpetual molecular motion of organic materials owing to the combination of its molecular shape and its particular HOMO configuration. Notably, ChDT derivatives exhibit excellent chemical and thermal stability, high charge‐carrier mobility under ambient conditions (μ ≤ 10 cm2 V−1 s−1), and a crystal phase that is highly stable, even at temperatures above 250 °C.

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V‐Shaped Organic Semiconductors With Solution Processability, High Mobility, and High Thermal Durability

Cited by 211 publications

References 27 publications

Liquid crystalline organic semiconductors for organic transistor applications

Liquid crystalline organic semiconductors for organic transistor applications

Correlation between thermal fluctuation effects and phase coherence factor in carrier transport of single-crystal organic semiconductors

Zigzag‐Elongated Fused π‐Electronic Core: A Molecular Design Strategy to Maximize Charge‐Carrier Mobility

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