A Highly π-Stacked Organic Semiconductor for Thin Film Transistors Based on Fused Thiophenes

Li, † Xiao-Chang; Sirringhaus, Henning; Garnier, F.; Holmes, Andrew B.; Moratti, Stephen C.; Feeder, Neil; Clegg, William; Teat, and Simon J.; Friend, Richard H.

doi:10.1021/ja9735968

Cited by 429 publications

(302 citation statements)

References 20 publications

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“…The amplitudes of the electronic splittings are observed to decay exponentially when the interchain distance is increased; this simply translates the exponential decay in intermolecular overlap of the -atomic orbitals when the two oligomers are pulled apart. An important result is that the electronic splittings vary by as much as a factor of three to four between 3.4 and 4.0 Å, a range that corresponds to the typical intermolecular distances found in organic conjugated crystals and films (46,47).…”

Section: Resultsmentioning

confidence: 96%

Organic semiconductors: A theoretical characterization of the basic parameters governing charge transport

Brédas

Calbert

Filho

et al. 2002

Proc. Natl. Acad. Sci. U.S.A.

1,210

993

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Organic semiconductors based on -conjugated oligomers and polymers constitute the active elements in new generations of plastic (opto)electronic devices. The performance of these devices depends largely on the efficiency of the charge-transport processes; at the microscopic level, one of the major parameters governing the transport properties is the amplitude of the electronic transfer integrals between adjacent oligomer or polymer chains. Here, quantum-chemical calculations are performed on model systems to address the way transfer integrals between adjacent chains are affected by the nature and relative positions of the interacting units. Compounds under investigation include oligothienylenes, hexabenzocoronene, oligoacenes, and perylene. It is shown that the amplitude of the transfer integrals is extremely sensitive to the molecular packing. Interestingly, in contrast to conventional wisdom, specific arrangements can lead to electron mobilities that are larger than hole mobilities, which is, for instance, the case of perylene. O rganic -conjugated materials offer remarkable potential as active elements in (opto)electronic devices that exploit their semiconducting properties, such as field-effect transistors (FETs; refs. 1-8), light-emitting diodes (LEDs; refs. 9-13), or photovoltaic and solar cells (14-17). Such devices are expected to be ultimately incorporated, for instance, into all-plastic integrated circuits for low-end and cheap electronics (7,8,18) and all-plastic light-emitting displays, where each pixel consists of an organic LED driven by an organic FET (19,20). In all of these applications, the efficiency of charge transport within the organic layer(s) plays a key role. In light-emitting diodes, it is desirable that the injected holes and electrons have large and similar mobilities to prevent electroluminescence quenching that can occur when charges recombine close to a metallic interface (21); high-charge mobilities favor recombination processes in the bulk (where charges can be confined further by means of organic-organic interfaces; ref. 22). In solar cells, the charges created upon photoexcitation of the active material have to be transported efficiently to be collected at the metallic contacts and stored under the form of electrical energy. Another challenge is to develop materials displaying high electron and hole mobilities in field-effect architectures to design complex organic circuits.The charge-transport properties critically depend on the degree of ordering of the chains in the solid state as well as on the density of chemical and͞or structural defects (23)(24)(25). This dependence explains why, over the last decades, the experimental characterization of the transport properties in organic thin films or crystals has led to results that vary with sample quality. Recently, the synthesis of ultra-pure single crystals of organic semiconductors such as oligoacenes has allowed Batlogg and coworkers (28) to demonstrate remarkable features that in many instances had been thought to be restricte...

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Section: Resultsmentioning

confidence: 96%

Organic semiconductors: A theoretical characterization of the basic parameters governing charge transport

Brédas

Calbert

Filho

et al. 2002

Proc. Natl. Acad. Sci. U.S.A.

1,210

993

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“…Dithieno[3,2-b:2',3'-d]thiophene (DTT) 1, a donor [13] with a planar core, had been extensively used in the construction of oligomeric [14][15][16][17][18][19][20][21][22][23] and polymeric [24][25][26] semiconductors.…”

Section: Introductionmentioning

confidence: 99%

Mixed-stack architecture and solvatomorphism of trimeric perfluoro-ortho-phenylene mercury complexes with dithieno[3,2-b:2′,3′-d]thiophene

Castañeda

Khrustalev

Fonari

et al. 2015

Journal of Molecular Structure

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This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. M A N U S C R I P T A C C E P T E D ACCEPTED MANUSCRIPT

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“…70 10 6 Tetrabenzoporphyrin [55] 10 -2 -6T [33] 0.002 -Tetra-phenyl porphyrin [56] 0.007～0.012 -BDT [35] 0.04 -Cyclo [8]pyrrole [57] 0. 68 10 4 TDT [36] 0.05 10 8 8T [58] 0.33 -DPh-BDX [37] 0.17 -DH-4T [59] 0. 06 10 6 DPh-BTBT [38] 2.00 10 7 DH-6T [59,60] 0.…”

Section: Figure 2 Schematic Of P-and N-channel Thin-film Transistors mentioning

confidence: 99%

Recent Progress of Semiconductors in Organic Thin-Film Transistors

Ma¹,

Wang²,

Guo³

et al. 2012

Chin. J. Org. Chem.

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A Highly π-Stacked Organic Semiconductor for Thin Film Transistors Based on Fused Thiophenes

Cited by 429 publications

References 20 publications

Organic semiconductors: A theoretical characterization of the basic parameters governing charge transport

Organic semiconductors: A theoretical characterization of the basic parameters governing charge transport

Mixed-stack architecture and solvatomorphism of trimeric perfluoro-ortho-phenylene mercury complexes with dithieno[3,2-b:2′,3′-d]thiophene

Recent Progress of Semiconductors in Organic Thin-Film Transistors

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