Core‐Fluorinated Perylene Bisimide Dyes: Air Stable n‐Channel Organic Semiconductors for Thin Film Transistors with Exceptionally High On‐to‐Off Current Ratios

Schmidt, R.; Ling, Mang Mang; Oh, Joon Hak; Winkler, Michael; Könemann, Martin; Bao, Zhenan; Würthner, Frank

doi:10.1002/adma.200701478

Cited by 234 publications

(153 citation statements)

References 22 publications

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“…In 2006, Ling et al [56] reported that two n-channel perylene diimide derivatives without strong electron-withdrawing groups showed high mobilities and air-stability; the devices still exhibited high mobilities above 0.1 cm 2 V À1 s À1 after storage in air for more than 80 days. Later, the same research groups developed another two core-fluorinated perylene bisimide dyes, PBI-F 2 and PBI-F 4 , [57] as air stable n-channel semiconductors for OTFTs. The PBI-F 2 devices showed high mobilities up to 0.34 cm 2 V À1 s À1 and an I on /I off of 10 8 in air.…”

Section: Naphthalene and Perylene Derivativesmentioning

confidence: 99%

Recent Progress in n‐Channel Organic Thin‐Film Transistors

2010

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Particular attention has been focused on n-channel organic thin-film transistors (OTFTs) during the last few years, and the potentially cost-effective circuitry-based applications in flexible electronics, such as flexible radiofrequency identity tags, smart labels, and simple displays, will benefit from this fast development. This article reviews recent progress in performance and molecular design of n-channel semiconductors in the past five years, and limitations and practicable solutions for n-channel OTFTs are dealt with from the viewpoint of OTFT constitution and geometry, molecular design, and thin-film growth conditions. Strategy methodology is especially highlighted with an aim to investigate basic issues in this field.

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Section: Naphthalene and Perylene Derivativesmentioning

confidence: 99%

Recent Progress in n‐Channel Organic Thin‐Film Transistors

2010

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“…the positions of the organic semiconductor units relative to each other. [ 3 ] The preferred organic semiconductor must be well ordered and stable with closely-packed molecules having few defects between molecules or domains. However, such uniform morphologies can also lead to the formation of molecular aggregates, which can quench luminescence and modify absorption spectra.…”

Section: Introductionmentioning

confidence: 99%

Ordered Materials for Organic Electronics and Photonics

2010

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We present a critical review of semiconducting/light emitting, liquid crystalline materials and their use in electronic and photonic devices such as transistors, photovoltaics, OLEDs and lasers. We report that annealing from the mesophase improves the order and packing of organic semiconductors to produce state-of-the-art transistors. We discuss theoretical models which predict how charge transport and light emission is affected by the liquid crystalline phase. Organic photovoltaics and OLEDs require optimization of both charge transport and optical properties and we identify the various trade-offs involved for ordered materials. We report the crosslinking of reactive mesogens to give pixellated full-colour OLEDs and distributed bi-layer photovoltaics. We show how the molecular organization inherent to the mesophase can control the polarization of light-emitting devices and the gain in organic, thin-film lasers and can also provide distributed feedback in chiral nematic mirrorless lasers. We update progress on the surface alignment of liquid crystalline semiconductors to obtain monodomain devices without defects or devices with spatially varying properties. Finally the significance of all of these developments is assessed.

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“…On the other hand, many of OTFTs have shown a large enhancement in carrier mobility through the thermal treatment during film deposition [29][30][31][33][34][35][36][37][40][41][42][43][44] and/or after film formation. [44][45][46][47][48][49][50][51] Materials with long alkyl chains, especially, have shown drastic morphological change after the thermal treatment, which lead to large change in the performance of TFT.…”

Section: -39mentioning

confidence: 99%

“…N , NЈ-dialkyl-3,4,9,10-perylene tetracarboxylic diimide ͑PTCDI-Cn͒, especially, is very promising n-type materials with a high electron mobility, and studied intensively from the first stage of researches on OTFTs. [14][15][16][17][26][27][28][29][30][31][32][33][34][35][36][37][38][39] For example, Horowitz et al have reported the first n-type organic TFT made of N , NЈ-diphenyl PTCDI 14 yr ago. 26 After 6 yr, Malenfant et al have reported a N,NЈ-dioctyl PTCDI TFT with fairly high electron mobility as high as 0.6 cm 2 / V s. 27 Jones et al have synthesized corecyanated PTCDI with fluorinated alkyl chains, and reported an air-stable TFT with electron mobility of 0.64 cm 2 / V s. 28 Chesterfield et al have reported strikingly high electron mobility in N , NЈ-dioctyl PTCDI TFT of up to 1.7 cm 2 / V s through exquisite control of deposition condition, 29 and after that many research groups have poured their efforts to develop high-mobility n-type PTCDI OTFTs by modifying the molecular structure with core-substitution or with changing the substituent on the imide N atoms, by controlling deposition condition, by optimizing device structure such as the surface state of dielectrics and electrode contact, and so on.…”

Section: Introductionmentioning

confidence: 99%

Thermal treatment effects on N-alkyl perylene diimide thin-film transistors with different alkyl chain

Jeon¹,

Hattori²,

Kato³

et al. 2010

Journal of Applied Physics

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The authors report that thermal treatment effect on various N , NЈ-dialkyl-3,4,9,10-perylene tetracarbxylic diimides ͓PTCDI-Cn, alkyl-dodecyl ͑n=12͒, butadecyl ͑n=14͒, octadecyl ͑n=18͔͒ thin-film transistors ͑TFTs͒ depends on the substituted alkyl chain length. It is clearly demonstrated that there are two kinds of molecular movements during the thermal treatment on PTCDI films; molecular rearrangement in the same layer and molecular migration from the lower layer to the upper layer. The former is directly related to the grain growth and can be controllable by applying an external electric field. The latter is also related not only to the grain growth but also to the formation of cracks between grains. These two movements show opposite dependence on the alkyl chain length during the thermal treatment; the former is more active in longer alkyl chain, but the latter in shorter one. However, they also have opposite effect to TFT performance, and PTCDI films with longer alkyl chains have great advantage on TFT performance for the thermal treatment. Consequently, PTCDI-C18 TFTs show the highest electron mobility as large as 1.2 cm 2 / V s after the thermal treatment at 140°C.

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Core‐Fluorinated Perylene Bisimide Dyes: Air Stable n‐Channel Organic Semiconductors for Thin Film Transistors with Exceptionally High On‐to‐Off Current Ratios

Cited by 234 publications

References 22 publications

Recent Progress in n‐Channel Organic Thin‐Film Transistors

Recent Progress in n‐Channel Organic Thin‐Film Transistors

Ordered Materials for Organic Electronics and Photonics

Thermal treatment effects on N-alkyl perylene diimide thin-film transistors with different alkyl chain

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