Functionalized dithieno[2,3-b:3′,2′-d]thiophenes (DTTs) for organic thin-film transistors

Kim, Choongik; Chen, Ming Chou; Chiang, Yen Ju; Guo, Yue Jhih; Youn, Jangdae; Huang, Hui; Liang, You; Lin, Yu Jou; Huang, Yu; Hu, Tarng Shiang; Lee, Gene Hsiang; Facchetti, Antonio; Marks, Tobin J.

doi:10.1016/j.orgel.2010.01.022

Cited by 65 publications

(13 citation statements)

References 64 publications

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“…6.5 10 À4 -5.2 10 À3 1.3 10 À2 -2.6 10 À2 5.4 10 À3 -0.02, 0.04-0.14 [c] 10 3.2 10 À7 -3.8 10 À2 5.7 10 À3 -9.0 10 À3 0.017-0.06 [b] 11…”

Section: Discussionunclassified

“…Furthermore, both oligothiophenes and oligoacenes in the bulk phase usually crystallize into face-to-edge packing, which does not provide optimal intermolecular p-orbital overlap for charge-transfer. To overcome these issues, a series of oligothienoacenes and their derivatives have been designed and synthesized [4][5][6][7][8][9][10][11][12] that have combined the chemical stability of the thiophene ring with the rigid planarity and extended conjugation of linear acenes. More importantly, oligothienoacenes and some functionalized derivatives favor face-to-face p-stacked crystal-packing structures, which would be beneficial for achieving higher carrier mobility.…”

Section: Introductionmentioning

confidence: 99%

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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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“…6.5 10 À4 -5.2 10 À3 1.3 10 À2 -2.6 10 À2 5.4 10 À3 -0.02, 0.04-0.14 [c] 10 3.2 10 À7 -3.8 10 À2 5.7 10 À3 -9.0 10 À3 0.017-0.06 [b] 11…”

Section: Discussionunclassified

Section: Introductionmentioning

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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“…For example, OFETs can be manufactured near room temperature on plastic and rubber. This temperature is not possible for silicon-based device [4]. Solution processing are also possible in wide range of organic materials.…”

Section: Introductionmentioning

confidence: 99%

Optical Characteristics of ITO/NTCDA Film for Defence Technology Application

Poad¹,

Demon²,

Yahya³

et al. 2018

IJCRSET

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The interface structure between inorganic/organic layer governed microscopic and physical property of many organic based devices. The 1,4,5,8-napthalenetetracarboxylic dianyhride (NTCDA) is strong electron acceptor and its thermal stability can be explored in electro-optics application and laser material. In this study, optical characteristics of NTCDA film at interface of indium tin oxide (ITO) was demonstrated. The film was processed using ethanol and toluene solvents at 1:1 ratio before spin coated on 180 nm thickness ITO substrate. Hexamethyldisilaze (HMDS) was used to surface functionalized the ITO substrate. Analysis of AFM images showed the NTCDA film grown on ITO substrate at grain size approximately 0.5-1.5 m. The onset of the absorption band shifted around 0.11 eV upon HMDS modification at interface of NTCDA film and ITO substrate indicating electronic modification on the bulk NTCDA film. Structural conformation was studied using the infrared absorption. Other than strong absorption peak at 1783 cm-1 that belonged to vibrational mode of the C = O functional group of the NTCDA, the fingerprint peaks of NTCDA on FTIR spectra were present with or without HMDS modification. This study showed the bandgap tuning of organic semiconductor film using surface functionalization technique as potential material processing in defence technology application.

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“…1,4-8 Jinyeol Kim et al reported the relationship between the microstructure of poly (3,4-ethylenedioxythiophene) and the conductivity by conducting atomic force microscope(C-AFM), showing that its conductivity gets higher as the film molecular arrangement is more orderly. 9,10 Recently, Mingchou Chen et al reported functionalized dithienothiophenes 11 and disubstituted tetrathienoacene 12 semiconductors for high performance organic thin-film transistors. They inferred that surface morphology had a great influence on device performance, and the highest carrier mobilities were generally obtained for films having the appropriate balance between large grain size and space-filling grain connectivity.…”

mentioning

confidence: 99%

Study on aggregation and electric properties in the micro-region of functionalized dithieno[2, 3-b: 3′, 2′-d]thiophene (DTT) oligomers

et al. 2016

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Three kinds of 2,5,-diphenyl-dithienol[2, 3-b: 3′, 2′-d]thiophene (DP-DTT), 2,5,-distyryl-dithienol[2, 3-b: 3′, 2′-d]thiophene (DEP-DTT) and 2,5,-thienyl-dithienol[2, 3-b: 3′, 2′-d]thiophene (DET-DTT) micro-region structure and electronic properties were studied. Thin films of these functionalized DTT oligomers were prepared in a one-step drop-casting deposition onto highly oriented pyrolytic graphite substrates. The surface structure of these films was characterized by atomic force microscopy (AFM). Conducting probe atomic force microscope (C-AFM) and Kelvin probe force microscope (KFM) were both used to characterize the electronic transport behavior and surface potential distribution. The substituents of DTT oligomers can greatly affect their aggregation and the hopping conductance mechanism was used to explain the Au-DTTs-HOPG junctions. KFM investigation revealed that these oligomers with different substituents have different highest occupied molecular orbital energy levels. The corresponding theoretical analysis reveals similar result to KFM characterization. The I-V results indicated that the aggregates of molecules were the dominating factor to their micro-region electrical transport.

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Functionalized dithieno[2,3-b:3′,2′-d]thiophenes (DTTs) for organic thin-film transistors

Cited by 65 publications

References 64 publications

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

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

Optical Characteristics of ITO/NTCDA Film for Defence Technology Application

Study on aggregation and electric properties in the micro-region of functionalized dithieno[2, 3-b: 3′, 2′-d]thiophene (DTT) oligomers

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