Novel Semiconducting Quinone for Air-Stable n-Type Organic Field-Effect Transistors

Mamada, Masashi; Kumaki, Daisuke; Nishida, Jun; Tokito, Shizuo; Yamashita, Yoshiro

doi:10.1021/am1001794

Cited by 51 publications

(51 citation statements)

References 46 publications

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“…This derivative has deep LUMO level of −4.1 eV, leading to efficient charge‐carrier injection and air stability. Comparable mobilities of 0.15 cm 2 V −1 s −1 in vacuum and 0.12 cm 2 V −1 s −1 in air were obtained 102. Compound 16a with new designed electronegative unit of 4,9‐dihydro‐ s ‐indaceno[1,2‐ b :5,6‐ b ′]‐dithiazole‐4,9‐dione (IDD), and trifluoromethyl and carbonyl groups, exhibited mobility of 0.39 cm 2 V −1 s −1 in vacuum and 0.14 cm 2 V −1 s −1 in air.…”

Section: N‐type Semiconductors For Ofetsmentioning

confidence: 80%

25th Anniversary Article: Recent Advances in n‐Type and Ambipolar Organic Field‐Effect Transistors

2013

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The advantages of organic field-effect transistors, such as low cost, mechanical flexibility and large-area fabrication, make them potentially useful for electronic applications such as flexible switching backplanes for video displays, radio frequency identifications and so on. A large amount of molecules were designed and synthesized for electron transporting (n-type) and ambipolar organic semiconductors with improved performance and stability. In this review, we focus on the advances in performance and molecular design of n-type and ambipolar semiconductors reported in the past few years.

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Section: N‐type Semiconductors For Ofetsmentioning

confidence: 80%

25th Anniversary Article: Recent Advances in n‐Type and Ambipolar Organic Field‐Effect Transistors

2013

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“…1a). 51 The crystal engineering silylethyne handle is added by routine ethynylation/ deoxygenation sequence to provide the desired core.…”

Section: Resultsmentioning

confidence: 99%

Computationally aided design of a high-performance organic semiconductor: the development of a universal crystal engineering core

et al. 2019

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Herein, we describe the design and synthesis of a suite of molecules based on a benzodithiophene "universal crystal engineering core". After computationally screening derivatives, a trialkylsilylethynebased crystal engineering strategy was employed to tailor the crystal packing for use as the active material in an organic field-effect transistor. Electronic structure calculations were undertaken to reveal derivatives that exhibit exceptional potential for high-efficiency hole transport. The promising theoretical properties are reflected in the preliminary device results, with the computationally optimized material showing simple solution processing, enhanced stability, and a maximum hole mobility of 1.6 cm 2 V À1 s À1 .

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“…Thus, mobilities of > 0.5 cm 2 V −1 s −1 were observed in some OSCs and air-stability could be provided by using a strong acceptor moiety. [29][30][31][32][33] However, these OSCs generally have low solubility in common organic solvents, even for molecules with perfluoroalkyl groups, 34 and few soluble derivatives have been developed because the substitution of solubilizing alkyl groups, which is frequently used strategy for p-type OSCs, seems to reduce the electron-accepting properties and disrupt molecular packing.…”

Section: Introductionmentioning

confidence: 99%

A Unique Solution-Processable n-Type Semiconductor Material Design for High-Performance Organic Field-Effect Transistors

et al. 2014

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There have been only a limited number of reports on solution-processed n-channel organic thin-film transistor (OTFT) devices with high levels of electrical performance, because the material design process for the n-type organic semiconductors are relatively difficult compared to p-type semiconductors, and further chemical modification of the functional groups are required. As a result, the development of soluble n-type organic semiconductors with high carrier mobilities has remained a challenge. Our work addresses this by introducing a novel molecular design to realize soluble n-type organic semiconductors with high electron mobilities, through the simple substitution of trifluoromethyl or trifluoromethoxy groups at meta-positions support sufficient solubility, creating suitable LUMO energy levels and high crystallinity. These newly designed benzobisthiadiazole (BBT)-based molecules showed electron mobilities as high as 0.61cm 2 V −1 s −1 in solution-processed OTFT devices. As a practical application in printed electronics, we demonstrated an organic complementary inverter circuit with OTFT devices using the developed soluble organic semiconductors. Due to their high solubility level and superior electrical properties compared to common para-derivatives, the utilization of meta-substituents is a new strategy for the design of soluble organic semiconductors in the field of OTFT device fabrication.

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Novel Semiconducting Quinone for Air-Stable n-Type Organic Field-Effect Transistors

Cited by 51 publications

References 46 publications

25th Anniversary Article: Recent Advances in n‐Type and Ambipolar Organic Field‐Effect Transistors

25th Anniversary Article: Recent Advances in n‐Type and Ambipolar Organic Field‐Effect Transistors

Computationally aided design of a high-performance organic semiconductor: the development of a universal crystal engineering core

A Unique Solution-Processable n-Type Semiconductor Material Design for High-Performance Organic Field-Effect Transistors

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