High-Performance Organic Semiconductors:  Asymmetric Linear Acenes Containing Sulphur

Tang, Ming Lee; Okamoto, Toshihiro; Bao, Zhenan

doi:10.1021/ja066824j

Cited by 217 publications

(162 citation statements)

References 21 publications

(28 reference statements)

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“…[1][2][3][4] The charge mobility of several kinds of OSC is now as large as 10 cm 2 ·V -1 ·s -1 in the thin films and single crystals [5][6][7][8][9][10] such as pentacene. But there are still some unsolved problems.…”

Section: Introductionmentioning

confidence: 99%

Theoretical Investigation on Charge Transfer Properties of 1,3,5-Tripyrrolebenzene (TPB) and its Derivatives with Electron-withdrawing Substituents

Hu¹,

Yin²,

Chaitanya³

et al. 2016

Croat. Chem. Acta

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Abstract:The electronic structures and charge transport properties of 1,3,5-tripyrrolebenzene (TPB) and its substituted derivatives with -F and -CN groups have been investigated by DFT calculations in combination with the Marcus hopping model. The dimer geometry was optimized by density functional theory method with dispersion force correction being included (DFT-D). Consequently, the charge transfer integral was evaluated. The calculation results show that the introduction of electron-withdrawing substituents does not significantly change the bond lengths and molecular symmetry of TPB, but lower the coplanarity between the pyrrole and benzene rings, especially in the case of CN substitution. Meanwhile, the introduction of electron-withdrawing groups can decrease the energy of the frontier molecular orbital and enhance the air stability. Fluorination makes the λe increase obviously while cyanation dose not. Generally speaking, the λe values of the title compounds are larger than their λh. Except for compounds 6 and 9, all others keep the face to face packing or have a slight slip in dimers, but the center of mass distances increase after fluorination or cyanation due to the distortion of the monomer's coplanarity. The predicted quasi-one-dimensional electron mobility of the dimers is up to 0.433 cm 2 ·V -1 ·s -1 at 298.15 K. The electron injection barriers of 2 and 7 are lower than that of TPB. The TPB derivatives of 1, 2, and 7 are potential n-channel materials with the high electron mobility.

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Section: Introductionmentioning

confidence: 99%

Theoretical Investigation on Charge Transfer Properties of 1,3,5-Tripyrrolebenzene (TPB) and its Derivatives with Electron-withdrawing Substituents

Hu¹,

Yin²,

Chaitanya³

et al. 2016

Croat. Chem. Acta

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“…[1][2][3][4] They have been widely investigated by various experimental and theoretical methods. [5][6][7][8][9] Their tremendous potential in the electronics process field arises from the advantages they bring in terms of cost and technological flexibility.…”

Section: Introductionmentioning

confidence: 99%

“…[3,8,15] More and more technical and academic studies of organic semiconductor materials have been carried out to develop high mobility electronic devices. [16][17][18][19] Bao and his coworkers have fabricated the high-performance single-crystal field-effect transistors with the synthesized organic semiconductors [1,2,20] and Shuai and his coworkers have systematically developed the theoretical models to simulate the charge transport in the organic conjugated systems. [21][22][23] However, due to a lack of stable molecular materials with strong electron injection and considerable electron mobility, investigations of n-type semiconductors have been limited compared with p-type ones.…”

Section: Introductionmentioning

confidence: 99%

Density functional theory study on electron and hole transport properties of organic pentacene derivatives with electron‐withdrawing substituent

et al. 2011

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Attaching electron-withdrawing substituent to organic conjugated molecules is considered as an effective method to produce n-type and ambipolar transport materials. In this work, we use density functional theory calculations to investigate the electron and hole transport properties of pentacene (PENT) derivatives after substituent and simulate the angular resolution anisotropic mobility for both electron and hole transport. Our results show that adding electronwithdrawing substituents can lower the energy level of lowest unoccupied molecular orbital (LUMO) and increase electron affinity, which are beneficial to the electron injection and ambient stability of the material. Also the LUMO electronic couplings for electron transport in these pentacene derivatives can achieve up to a hundred meV which promises good electron transport mobility, although adding electron-withdrawing groups will introduce the increase of electron transfer reorganization energy. The final results of our angular resolution anisotropic mobility simulations show that the electron mobility of these pentacene derivatives can get to several cm 2 V À1 s À1 , but it is important to control the orientation of the organic material relative to the device channel to obtain the highest electron mobility. Our investigation provide detailed information to assist in the design of n-type and ambipolar organic electronic materials with high mobility performance.

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“…The thienoacenes and their derivatives were also synthesized and investigated as semiconductors for p-type materials. The asymmetric oligoacene, such as the tetraceno-thiophene (6), was also synthesized and showed similar mobility (0.3 cm 2 V À1 s À1 ) compared to their centrosymmetric counterparts processed in the same conditions [42]. The tetrathienoacene (7) with aryl groups had a higher mobility up to 0.14 cm 2 V À1 s À1 by vapor deposition [43].…”

Section: P-type Semiconductorsmentioning

confidence: 99%

Organic Field-Effect Transistor: Device Physics, Materials, and Process

Chang¹,

Lin²,

Zhang³

et al. 2017

Different Types of Field-Effect Transistors - Theory and Applications

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Organic field-effect transistors have received much attention in the area of low cost, large area, flexible, and printable electronic devices. Lots of efforts have been devoted to achieve comparable device performance with high charge carrier mobility and good air stability. Meanwhile, in order to reduce the fabrication costs, simple fabrication conditions such as the printing techniques have been frequently used. Apart from device optimization, developing novel organic semiconductor materials and using thin-film alignment techniques are other ways to achieve high-performance devices and functional device applications. It is expected that by combining proper organic semiconductor materials and appropriate fabrication techniques, high-performance devices for various applications could be obtained. In this chapter, the organic field-effect transistor in terms of device physics, organic materials, device process, and various thin-film alignment techniques will be discussed.

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High-Performance Organic Semiconductors: Asymmetric Linear Acenes Containing Sulphur

Cited by 217 publications

References 21 publications

Theoretical Investigation on Charge Transfer Properties of 1,3,5-Tripyrrolebenzene (TPB) and its Derivatives with Electron-withdrawing Substituents

Theoretical Investigation on Charge Transfer Properties of 1,3,5-Tripyrrolebenzene (TPB) and its Derivatives with Electron-withdrawing Substituents

Density functional theory study on electron and hole transport properties of organic pentacene derivatives with electron‐withdrawing substituent

Organic Field-Effect Transistor: Device Physics, Materials, and Process

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