Air‐Stable n‐Channel Organic Single Crystal Field‐Effect Transistors Based on Microribbons of Core‐Chlorinated Naphthalene Diimide

He, Tao; Stolte, Matthias; Würthner, Frank

doi:10.1002/adma.201303392

Cited by 179 publications

(128 citation statements)

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“…1d: 35 , thus yielding first evidence that a different crystallographic phase has been obtained by sublimation, as will be confirmed by the detailed comparison of their single-crystal structures below (Supplementary Data 1-3). In the following, we will denote this polymorph by b-phase, whereas the formerly described phase 35 with smaller layer spacing is called a-phase. Based on these new results, we can now also re-assign the hitherto reported vacuum-processed thin-film transistors 31 to relate to the b-phase molecular packing arrangement.…”

Section: Resultsmentioning

confidence: 65%

“…Although our recently reported procedure towards high mobility SCFETs was based on ribbon-shaped crystals of Cl 2 -NDI grown by the drop-casting method on n-octadecyltriethoxysilane (OTES)-modified substrate and by solvent evaporation method ( Supplementary Fig. 1) 35 , the low molecular weight of Cl 2 -NDI (M ¼ 699 g mol À 1 ) and excellent air-stability suggested that this…”

Section: Resultsmentioning

confidence: 99%

“…For NDI small molecules, the highest mobilities could be obtained for thin-film transistors of DI-DTYM2 (3.5 cm 2 V À 1 s À 1 ) 34 and for single-crystal transistors of Cl 2 -NDI (8.6 cm 2 V À 1 s À 1 ) 35 , respectively, under ambient operation.…”

mentioning

confidence: 87%

“…In recent years, our group as well as others reported a significant number of naphthalene diimide (NDI)-based thin film transistor studies demonstrating excellent and stable n-channel operation even in air that can be attributed to a large electron affinity and close p-stacking [30][31][32][33][34][35][36] . For NDI small molecules, the highest mobilities could be obtained for thin-film transistors of DI-DTYM2 (3.5 cm 2 V À 1 s À 1 ) 34 and for single-crystal transistors of Cl 2 -NDI (8.6 cm 2 V À 1 s À 1 ) 35 , respectively, under ambient operation.…”

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confidence: 99%

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Single-crystal field-effect transistors of new Cl2-NDI polymorph processed by sublimation in air

et al. 2015

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Physical properties of active materials built up from small molecules are dictated by their molecular packing in the solid state. Here we demonstrate for the first time the growth of n-channel single-crystal field-effect transistors and organic thin-film transistors by sublimation of 2,6-dichloro-naphthalene diimide in air. Under these conditions, a new polymorph with two-dimensional brick-wall packing mode (b-phase) is obtained that is distinguished from the previously reported herringbone packing motif obtained from solution (a-phase). We are able to fabricate single-crystal field-effect transistors with electron mobilities in air of up to 8.6 cm 2 V À 1 s À 1 (a-phase) and up to 3.5 cm 2 V À 1 s À 1 (b-phase) on n-octadecyltriethoxysilane-modified substrates. On silicon dioxide, thin-film devices based on b-phase can be manufactured in air giving rise to electron mobilities of 0.37 cm 2 V À 1 s À 1 . The simple crystal and thin-film growth procedures by sublimation under ambient conditions avoid elaborate substrate modifications and costly vacuum equipment-based fabrication steps.

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Section: Resultsmentioning

confidence: 65%

Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 87%

mentioning

confidence: 99%

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Single-crystal field-effect transistors of new Cl2-NDI polymorph processed by sublimation in air

et al. 2015

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“…Dichlorinated NDI based molecular semiconductors 1l and 1m with different fluoroalkyl chains show identical LUMO energy levels of À4.01 eV. 139,147 Compound 1l exhibits electron mobilities of 0. 86 ) when the device is stored in air for 82 days.…”

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Trends in molecular design strategies for ambient stable n-channel organic field effect transistors

2017

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aIn recent years, organic semiconducting materials have enabled technological innovation in the field of flexible electronics. Substantial optimization and development of new p-conjugated materials has resulted in the demonstration of several practical devices, particularly in displays and photoreceptors.However, applications of organic semiconductors in bipolar junction devices, e.g. rectifiers and inverters, are limited due to an imbalance in charge transport. The performance of p-channel organic semiconducting materials exceeds that of electron transport. In addition, electron transport in p-conjugated materials exhibits poorer atmospheric stability and dispersive transient photocurrents due to extrinsic carrier trapping. Thus development of air stable n-channel conjugated materials is required. New classes of materials with delocalized n-doped states are under development, aiming at improvement of the electron transport properties of organic semiconductors. In this review, we highlight the basic tenets related to the stability of n-channel organic semiconductors, primarily focusing on the thermodynamic stability of anions and summarizing the recent progress in the development of air stable electron transporting organic semiconductors. Molecular design strategies are analysed with theoretical investigations.

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Understanding Polymorph Transformations in Core‐Chlorinated Naphthalene Diimides and their Impact on Thin‐Film Transistor Performance

Purdum

Yao

Woll

et al. 2015

Adv Funct Materials

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Though charge transport is sensitive to subtle changes in the packing motifs of molecular semiconductors, research addressing how intermolecular packing influences electrical properties has largely been carried out on single‐crystals, as opposed to the more technologically relevant thin‐film transistors (TFTs). Here, independent and reversible access to the monoclinic and triclinic crystal structures of a core‐chlorinated naphthalene tetracarboxylic diimide (NTCDI‐1) is demonstrated in polycrystalline thin films via post‐deposition annealing. Time‐resolved measurements of these transitions via UV–visible spectroscopy and grazing‐incidence X‐ray diffraction indicate that the polymorphic transformations follow second‐order Avrami kinetics, suggestive of 2D growth after initial nucleation. Thin‐film transistors comprising triclinic NTCDI‐1 consistently outperform those comprising its monoclinic counterpart. This behavior contrasts that of single‐crystal transistors in which devices comprising monoclinic crystals are consistently superior to devices with triclinic crystals. This difference is attributed to more uniform in‐plane charge transport in polycrystalline thin films having the triclinic compared to the monoclinic polymorph. As the mobility of TFTs is a reflection of ensemble‐average charge transport across crystalline grains having different molecular orientations, this study suggests that among different polymorphs of a particular molecular semiconductor, those with smaller in‐plane anisotropy are more beneficial for efficient lateral charge transport in polycrystalline devices.

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Air‐Stable n‐Channel Organic Single Crystal Field‐Effect Transistors Based on Microribbons of Core‐Chlorinated Naphthalene Diimide

Cited by 179 publications

References 44 publications

Single-crystal field-effect transistors of new Cl2-NDI polymorph processed by sublimation in air

Single-crystal field-effect transistors of new Cl2-NDI polymorph processed by sublimation in air

Trends in molecular design strategies for ambient stable n-channel organic field effect transistors

Understanding Polymorph Transformations in Core‐Chlorinated Naphthalene Diimides and their Impact on Thin‐Film Transistor Performance

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