Highly Soluble [1]Benzothieno[3,2-<i>b</i>]benzothiophene (BTBT) Derivatives for High-Performance, Solution-Processed Organic Field-Effect Transistors

Ebata, Hideaki; Izawa, Takafumi; Miyazaki, Eigo; Takimiya, Kazuo; Ikeda, Masaaki; Kuwabara, Hirokazu; Yui, Tatsuto

doi:10.1021/ja074841i

Cited by 886 publications

(791 citation statements)

References 16 publications

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“…100°C in dialkyl BTBTs. 4 The adoption of larger core systems such as DNTT 5 and DNBDT 7 unfortunately always result in poor solubility because of a trade-off between the solubility in solvents and the melting point, so that it is quite difficult to satisfy both requirements. …”

Section: Small-molecule Ofet Materialsmentioning

confidence: 99%

“…There have been many reports on the FET performance of OFETs fabricated from crystalline thin films of liquid crystals including di-thienyl-naphthalene, 23 hexabenzocoronene, 24 bis-(5'-hexylthiophen-2'-yl)-2,6-Anthracene 25 and dialkyl-BTBT derivatives, 4 as shown in Figure 3. However, the liquid crystallinity in these materials was overlooked, and its benefits have not been utilized in device fabrication.…”

Section: Liquid Crystalline Semiconductors For Ofets H Iino and J Hannamentioning

confidence: 99%

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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%

Section: Liquid Crystalline Semiconductors For Ofets H Iino and J Hannamentioning

confidence: 99%

Liquid crystalline organic semiconductors for organic transistor applications

Iino

Hanna

2016

Polym J

101

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“…We select C 8 -BTBT because it is among the highest mobility small-molecule organic materials [12][13][14] . Graphene and BN are also ideal substrates as they are atomically flat without dangling bonds 15 .…”

mentioning

confidence: 99%

Two-dimensional quasi-freestanding molecular crystals for high-performance organic field-effect transistors

et al. 2014

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Two-dimensional atomic crystals are extensively studied in recent years due to their exciting physics and device applications. However, a molecular counterpart, with scalable processability and competitive device performance, is still challenging. Here, we demonstrate that high-quality few-layer dioctylbenzothienobenzothiophene molecular crystals can be grown on graphene or boron nitride substrate via van der Waals epitaxy, with precisely controlled thickness down to monolayer, large-area single crystal, low process temperature and patterning capability. The crystalline layers are atomically smooth and effectively decoupled from the substrate due to weak van der Waals interactions, affording a pristine interface for high-performance organic transistors. As a result, monolayer dioctylbenzothienobenzothiophene molecular crystal field-effect transistors on boron nitride show record-high carrier mobility up to 10 cm 2 V À 1 s À 1 and aggressively scaled saturation voltage B1 V. Our work unveils an exciting new class of two-dimensional molecular materials for electronic and optoelectronic applications.

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“…It is noteworthy that the obvious phase transitions from the initial crystal phases of C 10 –ChDT and C 10 –Th–ChDT occur above 280 and 254 °C, respectively; these values are extremely high compared to other linear‐shaped π‐cores such as decyl‐substituted pentacene, BTBT , and DNTT (cf. C 10 –pentacene: 89 °C; C 10 –BTBT : 110 °C; C 10 –DNTT : 108 °C) 23, 24, 25. Interestingly, ChDT derivatives exhibit more promising thermally stabilized crystal phases than the previously reported V‐shaped C 10 –DNT–VW (150 °C) and the N‐shaped C 10 –DNBDT–NW (217 °C) 5, 16.…”

Section: Resultsmentioning

confidence: 99%

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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Highly Soluble [1]Benzothieno[3,2-b]benzothiophene (BTBT) Derivatives for High-Performance, Solution-Processed Organic Field-Effect Transistors

Cited by 886 publications

References 16 publications

Liquid crystalline organic semiconductors for organic transistor applications

Liquid crystalline organic semiconductors for organic transistor applications

Two-dimensional quasi-freestanding molecular crystals for high-performance organic field-effect transistors

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

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