On the Air Stability of <i>n</i>-Channel Organic Field-Effect Transistors: A Theoretical Study of Adiabatic Electron Affinities of Organic Semiconductors

Chang, Yu‐Chang; Kuo, Ming‐Yu; Chen, Chih‐Ping; Lu, Hsiu‐Feng; Chao, Ito

doi:10.1021/jp1025625

Cited by 140 publications

(103 citation statements)

References 63 publications

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“…38,49 However, its stability in ambient conditions could be compromised by high EA values as well as other factors as the crystal packing and film morphology. 38,[50][51][52] The adiabatic (AEA) and vertical (VEA) electron affinity were calculated as follows…”

Section: Theoretical Methodologymentioning

confidence: 99%

Bis(arylene-ethynylene)-s-tetrazines: A Promising Family of n-Type Organic Semiconductors?

et al. 2015

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We theoretically describe in this work the n-type semiconducting behavior of a set of bis(arylene-ethynylene)-s-tetrazines ((ArCC) 2 Tz), by comparing their electronic properties with those of their parent diaryl-s-tetrazines (Ar 2 Tz) after the introduction of ethynylene bridges. The significantly reduced internal reorganization energy for electron transfer is ascribed to an extended delocalization of the LUMO for (ArCC) 2 Tz as opposite to that for Ar 2 Tz, which was described mostly localized on the s-tetrazine ring. The largest electronic coupling and the corresponding electron transfer rates found 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 2 for bis(phenyl-ethynylene)-s-tetrazine, as well as for some halogenated derivatives, are comparable to those reported for the best performing n-type organic semiconductors materials such as diimides and perylenes. The theoretical mobilities for the studied compounds turn out to be in the range 0.3 -1.3 cm 2 V −1 s −1 , close to values experimentally determined for common n-type organic semiconductors used in real devices. In addition, ohmic contacts can be expected when these compounds are coupled to metallic cathodes such as Na, Ca and Sm. For these reasons, the future application of semiconducting bis(phenyl-ethynylene)-s-tetrazine and its fluorinated and brominated derivatives in optoelectronic devices is envisioned.

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Section: Theoretical Methodologymentioning

confidence: 99%

Bis(arylene-ethynylene)-s-tetrazines: A Promising Family of n-Type Organic Semiconductors?

et al. 2015

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“…However, the calculated EAs were all below the threshold value for air stability (2.8 or 3.0 eV). [25,26] Thus, OFETs based on these derivatives did not display stable n-channel properties under ambient conditions, owing to the larger barrier for electron injection from the workfunction of a gold electrode to the LUMO of organic semiconductors.…”

Section: Vertical Electron Affinities Vertical Ionization Potentialsmentioning

confidence: 99%

First‐Principles Investigation of the Electronic and Conducting Properties of Oligothienoacenes and their Derivatives

Huang

Wen

Han

2012

Chemistry An Asian Journal

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Herein, we calculated reorganization energies, vertical ionization energies, electron affinities, and HOMO–LUMO gaps of fused thiophenes and their derivatives, and analyzed the influence of different substituents on their electronic properties. Furthermore, we simulated the angular resolution anisotropic mobility for both electron‐ and hole‐transport, based on quantum‐chemical calculations combined with the Marcus–Hush electron‐transfer theory. We showed that: 1) styrene‐group substitution can effectively elevate the HOMO energy level and lower the LUMO energy level, and therefore lower both the hole‐ and electron‐injection barriers; and 2) chemical oxidation of the thiophene ring can significantly improve the semiconductor properties of the fused oligothiophenes through a decrease of the injection barrier and an increase in the charge‐transfer mobility for electrons but without lowering their hole‐transfer mobilities, which suggests that it may be a promising way to convert p‐type semiconductors into ambipolar or n‐type semiconductor materials.

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“…Chao and co-workers have determined the minimum value of EA to be 2.8 eV to achieve ambient-stable n-channel operation from theoretical calculations on a large number of organic semiconductors. 59 Therefore, inclusion of strong electron withdrawing groups to enhance the EA is a simple but effective approach to develop ambient stable n-channel organic semiconductors. The EAs should not be too large, however, as organic molecules with EAs above 4.5 eV are prone to unintentional n-doping, leading to loss of semiconducting properties.…”

mentioning

confidence: 99%

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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On the Air Stability of n-Channel Organic Field-Effect Transistors: A Theoretical Study of Adiabatic Electron Affinities of Organic Semiconductors

Cited by 140 publications

References 63 publications

Bis(arylene-ethynylene)-s-tetrazines: A Promising Family of n-Type Organic Semiconductors?

Bis(arylene-ethynylene)-s-tetrazines: A Promising Family of n-Type Organic Semiconductors?

First‐Principles Investigation of the Electronic and Conducting Properties of Oligothienoacenes and their Derivatives

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

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