Molecular Design and Synthetic Approaches to Electron-Transporting Organic Transistor Semiconductors

Jung, Bernhard; Tremblay, Noah J.; Yeh, Ming-Ling; Katz, Howard E.

doi:10.1021/cm102296d

Cited by 210 publications

(156 citation statements)

References 181 publications

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“…Naphthalene tetracarboxylic diimide (NTCDI, Scheme 1) is a representative n-type organic semiconductor, [1][2][3][4][5][6][7][8][9][10][11] and in particular the cyclohexyl derivative (Cy6-NTCDI, Scheme 1) shows an electron mobility as high as 6.2 cm 2 V À1 s À1 , 11 which is one of the highest among the n-type organic eld-effect transistors. In contrast, the n-hexyl derivative (n6-NTCDI, Scheme 1) shows an electron mobility of only 0.1 cm 2 V À1 s À1 .…”

Section: Introductionmentioning

confidence: 99%

Correlation of mobility and molecular packing in organic transistors based on cycloalkyl naphthalene diimides

et al. 2013

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A series of cycloalkyl-substituted naphthalene tetracarboxylic diimides (Cyn-NTCDIs, n ¼ 3-8) are prepared and the transistor properties and molecular packings are systematically investigated. Cy5-Cy8-NTCDIs have similar brickwork structures, where two molecules are located on the top of a molecule with large displacement along the molecular short axis. The intermolecular overlap is maximized when the small slipping along the molecular long axis makes the molecules nearly perpendicular to the substrate.Consequently, the mobility decreases exactly in the same order as the interlayer d-spacings.

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Section: Introductionmentioning

confidence: 99%

Correlation of mobility and molecular packing in organic transistors based on cycloalkyl naphthalene diimides

et al. 2013

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“…In any case, once hole/electrode injection from the source electrode has been maximized, charges should be able to hop from molecule to molecule until they reach the drain electrode. [11] Thus, another factor that can compromise ambipolar transport in organic semiconductors is poor solidstate overlap between the HOMO (for holes) or LUMO (for electrons) orbitals of neighboring molecules in the semiconductor thin film.…”

Section: Introductionmentioning

confidence: 99%

Rational Design of Ambipolar Organic Semiconductors: Is Core Planarity Central to Ambipolarity in Thiophene–Naphthalene Semiconductors?

Ortiz

Herrera

Seoane

et al. 2011

Chemistry A European J

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Herein, we report a new family of naphthaleneamidinemonoimide-fused oligothiophene semiconductors designed for facile charge transport in organic field-effect transistors (OFETs). These molecules have planar skeletons that induce high degrees of crystallinity and hence good charge-transport properties. By modulating the length of the oligothiophene fragment, the majority carrier charge transport can be switched from n-type to ambipolar behavior. The highest FET performance is achieved for solution-processed films of 10-[(2,2'-bithiophen)-5-yl]-2-octylbenzo[lmn]thieno[3',4':4,5]imidazo[2,1-b][3,8]phenanthroline-1,3,6(2H)-trione (NDI-3 Tp), with optimized film mobilities of 2×10(-2) and 0.7×10(-2) cm(2) V(-1) s(-1) for electrons and holes, respectively. Finally, these planar semiconductors are compared with their twisted-skeleton counterparts, which exhibit only n-type mobility, in order to understand the origin of the ambipolarity in this new series of molecular semiconductors.

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“…This is achieved by functionalizing the p-conjugated aromatic backbone with halogen atoms, mainly fluorine, to create a kinetic barrier. 87 Fluorination also increases the hydrophobicity of organic materials. Since fluorine is very small and leads to strong hydrogen bridging, substitution with fluorine may additionally improve the structural features and strengthen the molecular organization.…”

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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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Molecular Design and Synthetic Approaches to Electron-Transporting Organic Transistor Semiconductors

Cited by 210 publications

References 181 publications

Correlation of mobility and molecular packing in organic transistors based on cycloalkyl naphthalene diimides

Correlation of mobility and molecular packing in organic transistors based on cycloalkyl naphthalene diimides

Rational Design of Ambipolar Organic Semiconductors: Is Core Planarity Central to Ambipolarity in Thiophene–Naphthalene Semiconductors?

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

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