Improved ambient operation of n-channel organic transistors of solution-sheared naphthalene diimide under bias stress

Stolte, Matthias; Gsänger, Marcel; Hofmockel, Robert; Suraru, Sabin–Lucian; Würthner, Frank

doi:10.1039/c2cp41552f

Cited by 44 publications

(32 citation statements)

References 35 publications

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“…The combined effect of electron-withdrawing halogen substituents at the core and fluorinated alkyl chains in the imide position results in a further decrease of the redox potentials, hence the first reduction of dichlorinated derivatives 10 a (R 1 = CH 2 C 3 F 7 ) and 10 b (R 1 = CH 2 C 4 F 9 ) appears at À0.79 V, which corresponds to a LUMO energy of about À4 eV relative to the vacuum level (Scheme 6). The outstanding electron mobilities of greater than 1 cm 2 V À1 s À1 in vacuum- [51] and in solution-processed [52] thin-film transistors, as well as up to 8.6 cm 2 V À1 s À1 in singlecrystal transistors (Figure 5), [29] combined with their very high air-stability, make the NDI derivaties 10 a,b exceptional . Schematic representation of the influence of core substituents on the energy levels of the frontier orbitals of selected NDI derivatives and a selection of the corresponding UV/Vis spectra.…”

Section: Core Functionalization With Nucleophilesmentioning

confidence: 98%

Strategies for the Synthesis of Functional Naphthalene Diimides

2014

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Naphthalene diimides, which have for a long time been in the shadow of their higher homologues the perylene diimides, currently belong to the most investigated classes of organic compounds. This is primarily due to the initial synthetic studies on core functionalization that were carried out at the beginning of the last decade, which facilitated diverse structural modifications of the naphthalene scaffold. Compounds with greatly modified optical and electronic properties that can be easily and effectively modulated by appropriate functionalization were made accessible through relatively little synthetic effort. This resulted in diverse interesting applications. The electron-deficient character of these compounds makes them highly valuable, particularly in the field of organic electronics as air-stable n-type semiconductors, while absorption bands over the whole visible spectral range through the introduction of core substituents enabled interesting photosystems and photovoltaic applications. This Review provides an overview on different approaches towards core functionalization as well as on synthetic strategies for the core expansion of naphthalene diimides that have been developed mainly in the last five years.

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Section: Core Functionalization With Nucleophilesmentioning

confidence: 98%

Strategies for the Synthesis of Functional Naphthalene Diimides

2014

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“…[13][14][15][16][17] Perylene and naphthalene tetracarboxylic bisimides (PDIs and NDIs) were among the most used structures from the early stages in the development of n-type OSCs due to the ease of synthesis, chemical stability and high electron accepting properties. [18][19][20][21][22][23][24] Moreover, perfluorophenyl and perfluoroalkyl-substituted OSCs have also been widely developed by incorporating thiophene/phenylene backbones. [25][26][27][28] The advantages of latter OSCs are the availability of various building blocks and ease in fine-tuning its the material properties.…”

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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“…The improvement in mobilities was attributed to the trapping of the charge carriers by ambient oxidants. Furthermore, 241a-based OFETs fabricated by solution shearing technique, afforded electron mobility increased up to 4.26 cm 2 V −1 s −1 under bias stress after 1000 cycles [303], and the single crystal FET devices of 241a showed higher mobilities of up to 8.6 cm 2 V −1 s −1 [304]. The cyano-substituted derivative, 242 afforded a low mobility of about 4.7 × 10 −3 cm 2 V −1 s −1 , whereas dicyano substituted derivative 243 exhibited an electron mobility of 0.15 cm 2 V −1 s −1 , which is comparable to that of 240c unsubstituted by cyano groups [305].…”

Section: Diimidesmentioning

confidence: 98%

Organic Semiconductors for Field-Effect Transistors

Zhang

2015

Lecture Notes in Chemistry

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An important application of organic semiconductors is to fabricate organic field-effect transistors (OFETs) which are essential building blocks for the next generation of organic circuits. In terms of molecular size or molecular weight, organic semiconductors can be divided into small-molecule and polymer semiconductors, and thus their corresponding OFETs can also be categorized into organic small molecule OFETs and polymer field-effect transistors (PFETs). On the basis of the main charge carriers transporting in OFET channels, organic semiconductors can be further divided into p-type, n-type, and ambipolar semiconducting materials. According to the characteristic of the organic semiconductors, the OFETs can be classified into two types: organic thin film transistors (OTFTs) and organic single crystal transistors. In any kind of OFET devices, organic semiconductor materials are the core; their properties determine the performance of the electronic devices. Therefore, the design and synthesis of high performance organic semiconductor materials are the basis and premise of the wide application of OFET devices. In the past few decades, great progress has been made in developing organic semiconductors. Besides organic semiconducting materials, there are many other factors influencing the performance of OFETs including device configuration, processing technique, and other devices physical factors, etc. In the following, a brief review of the development of p-type, n-type, ambipolar organic semiconductors and their field-effect properties is given. The history, mechanism, configuration, and fabrication methods of OFET devices and main performance influencing factors of OFETs are also introduced.

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Improved ambient operation of n-channel organic transistors of solution-sheared naphthalene diimide under bias stress

Cited by 44 publications

References 35 publications

Strategies for the Synthesis of Functional Naphthalene Diimides

Strategies for the Synthesis of Functional Naphthalene Diimides

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

Organic Semiconductors for Field-Effect Transistors

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