Organic Single Crystal Field‐effect Transistors Based on 6H‐pyrrolo[3,2–b:4,5–b´]bis[1,4]benzothiazine and its Derivatives

Wei, Zhongming; Hong, Wei; Geng, Hua; Chen, YangQuan; Liu, Yaling; Li, Rongjin; Xu, Wei; Shuai, Zhigang; Hu, Wenping; Wang, Quanrui; Zhu, Daoben

doi:10.1002/adma.201000088

Cited by 56 publications

(43 citation statements)

References 31 publications

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“…One possible interpretation is that, in a 1D crystal, the electrical transport should be more easily interrupted by the defects, whereas a crystal with 2D electrical transport network should possess higher tolerance towards the defects. We have previously observed a similar situation in single crystals of 6H‐pyrrolo[3,2‐b:4,5‐b′] bis[1,4]benzothiazine and its derivatives …”

Section: Methodssupporting

confidence: 64%

Charge‐Transfer Complex Crystal Based on Extended‐π‐Conjugated Acceptor and Sulfur‐Bridged Annulene: Charge‐Transfer Interaction and Remarkable High Ambipolar Transport Characteristics

et al. 2014

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Section: Methodssupporting

confidence: 64%

Charge‐Transfer Complex Crystal Based on Extended‐π‐Conjugated Acceptor and Sulfur‐Bridged Annulene: Charge‐Transfer Interaction and Remarkable High Ambipolar Transport Characteristics

et al. 2014

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“…In vapor‐grown single crystals of pyrrolobisbenzothiazine with cofacial, 2D π – π stacking mobilities of up to 3.6 cm 2 /V s were reported on octadecyltrichlorosilane (OTS) modified SiO 2 . Derivatives substituted with C 8 H 17 on the central nitrogen position exhibited more 1D π – π stacking and reduced mobilities up to 0.4 cm 2 /V s 27. Interestingly, in 3,10‐dimethyl substituted DNTT, an unusual 3D‐herringbone stacking was observed due to slippage of one of the molecules in the unit cell along the c ‐direction.…”

Section: Review Of Recent High‐mobility Small‐molecule and Polymer mentioning

confidence: 99%

Charge‐transport physics of high‐mobility molecular semiconductors

Sirringhaus

Sakanoue

Chang

2012

Physica Status Solidi (b)

100

124

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This review is focused on understanding of the charge-transport physics of high-mobility organic semiconductors at a molecular level. We review recent high-mobility small-molecule and conjugated polymer materials with a focus on crystalline materials that have been able to exceed mobilities of 0.5-1 cm 2 /V s. We discuss some of the main, competing factors that govern charge transport in these materials and present theoretical approaches that have been developed to describe systems in which moderately strong intermolecular electronic interactions and strong electron-phonon interactions are present. Finally, we review recent experimental results that have aimed to address the important question of whether at room-temperature charge carriers in these high-mobility organic semiconductors are in fact simply extended Bloch electrons that undergo occasional scattering processes or are localized on individual molecules and move by hopping. 1 Introduction There has been tremendous progress in discovering new classes of organic semiconductors, that provide field-effect mobilities, m, above 1 cm 2 /V s and allow addressing increasingly demanding thin-film electronic applications [1]. For many years, the performance of organic field-effect transistors (OFETs) seemed to be inherently lower than that of their inorganic counterparts, in particular, compared to amorphous silicon (a-Si) and polycrystalline FETs which have characteristic mobilities of the order of 0.5-1 and 100 cm 2 /V s, respectively. Due to extensive materials development and evaluation of different classes of organic semiconductors there is now a broad range of organic semiconductors, both vacuum and solution processible, as well as small-molecule and conjugated polymer based, which are able to reach mobility values exceeding that of a-Si. The processing characteristics of these materials make them suitable for applications that cannot easily be addressed by many inorganic materials. Organic semiconductors are inherently low-temperature materials. Because of the absence of covalent bonding between molecules, they can be processed at temperatures below typically 100-150 8C

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“…[1][2][3][4][5][6][7] In the past two decades, the performances of OFETs have been significantly enhanced as a result of intense research efforts towards the development of new p-conjugated semiconducting materials. [8][9][10][11][12][13][14][15] Among the most successful molecular building blocks, diketopyrrolopyrrole (DPP) has attracted considerable attention for the construction of a large number of organic semiconductors because of its electron-deficient nature, planar skeleton, and ability to form hydrogen bonds. [16][17][18][19] There also exist numerous reports on DPP-based high-performance polymers.…”

Section: Introductionmentioning

confidence: 99%

Thieno[3,2‐b]thiophene‐Diketopyrrolopyrrole‐Based Quinoidal Small Molecules: Synthesis, Characterization, Redox Behavior, and n‐Channel Organic Field‐Effect Transistors

Wang

Zang

Qin

et al. 2014

Chemistry A European J

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We report the synthesis, characterization, redox behavior, and n-channel organic field-effect (OFET) characteristics of a new class of thieno[3,2-b]thiophene-diketopyrrolopyrrole-based quinoidal small molecules 3 and 4. Under ambient atmosphere, solution-processed thin-film transistors based on 3 and 4 exhibit maximum electron mobilities up to 0.22 and 0.16 cm(2) V(-1) s(-1) , respectively, with on-off current ratios (Ion /Ioff ) of more than than 10(6) . Cyclic voltammetry analysis showed that this class of quinoidal derivatives exhibited excellent reversible two-stage reduction behavior. This property was further investigated by a stepwise reductive titration of 4, in which sequential reduction to the radical anion and then the dianion were observed.

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Organic Single Crystal Field‐effect Transistors Based on 6H‐pyrrolo[3,2–b:4,5–b´]bis[1,4]benzothiazine and its Derivatives

Cited by 56 publications

References 31 publications

Charge‐Transfer Complex Crystal Based on Extended‐π‐Conjugated Acceptor and Sulfur‐Bridged Annulene: Charge‐Transfer Interaction and Remarkable High Ambipolar Transport Characteristics

Charge‐Transfer Complex Crystal Based on Extended‐π‐Conjugated Acceptor and Sulfur‐Bridged Annulene: Charge‐Transfer Interaction and Remarkable High Ambipolar Transport Characteristics

Charge‐transport physics of high‐mobility molecular semiconductors

Thieno[3,2‐b]thiophene‐Diketopyrrolopyrrole‐Based Quinoidal Small Molecules: Synthesis, Characterization, Redox Behavior, and n‐Channel Organic Field‐Effect Transistors

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