FET performance and substitution effect on 2,6-dithienylanthracene devices prepared by photoirradiation of their diketone precursors

Yamada, Hiroko; Ohashi, Chika; Aotake, Tatsuya; Katsuta, Shuhei; Honsho, Yoshihito; Kawano, Hiroyuki; Okujima, Tetsuo; Uno, Hidemitsu; Ono, Noboru; Seki, Shu; Nakayama, Keiichi I.

doi:10.1039/c2cc35439j

Cited by 20 publications

(16 citation statements)

References 29 publications

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“…In this context, introducing the -diketone unit to already known, high performance organic semiconductors is highly beneficial, because it endows organic semiconductors of interest with higher solubility, thereby potentially allowing device fabrication based on solution techniques. Along these lines, Yamada et al developed -diketone-type precursors of substituted anthracenes (101a-101c, Scheme 16) [92,93]. It was successfully demonstrated that these -diketone derivatives can be photolyzed in films to afford 102a-102c.…”

Section: Synthesis Of End-substituted Pentacenes Via -Diketone-type mentioning

confidence: 99%

“…In OFET materials, side alkyl chains are often employed to increase solubility and align the molecules perpendicularly on a hydrophobic surface [108]. The effect of alkyl chains in photoconvertible materials was investigated using anthracene diketone derivatives 101b and 101c (Scheme 16) [93]. The FET mobilities in the thin films obtained from 101b and 101c were estimated to be 4.7 × 10 -2 and 2.6 × 10 -4 cm 2 V -1 s -1 , respectively.…”

Section: Organic Field-effect Transistorsmentioning

confidence: 99%

“…Importantly, this photoprecursor method does not require high temperature, and thus would be compatible with thermolabile substrates such as plastic. Successful application of this method to the fabrication of organic transistors and solar cells has been demonstrated [93,106,113].…”

Section: Summary and Concluding Remarksmentioning

confidence: 99%

“…(a) XRD patterns of the thin films of 102b and 102c prepared from the corresponding photoconvertible precursors 101b and 101c, respectively, on Si/SiO2 substrates (b) (100) and (011) planes in single-crystal structure of 102c[93].…”

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confidence: 99%

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Synthesis and photoreactivity of α-diketone-type precursors of acenes and their use in organic-device fabrication

Suzuki

Aotake

Yamaguchi

et al. 2014

Journal of Photochemistry and Photobiology C: Photochemistry Re

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Acenes are highly promising p-type organic semiconductors, and have been the subject of intense studies. However, acenes are often low in solubility and stability, which poses major obstacles in the synthesis and processing of this class of compounds. In order to overcome the problem, a series of diketone-type acene precursors have been developed. These precursors are generally more soluble and stable than the corresponding acene compounds, and their quantitative conversion can be achieved simply by photoirradiation both in solution and in the solid state. Further, the irreversible photoinduced removal of the -diketone unit can be used to alter the optoelectronic properties of fluorophores. This review overviews the synthesis and photochemical properties of -diketone-type acene precursors, as well as their use as intermediates in preparation of large acenes or highly functionalized acene derivatives. Computational studies on the mechanism of -diketone photolysis and the use of diketone derivatives in fabrication of organic devices are also summarized in this review.

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Section: Synthesis Of End-substituted Pentacenes Via -Diketone-type mentioning

confidence: 99%

Section: Organic Field-effect Transistorsmentioning

confidence: 99%

Section: Summary and Concluding Remarksmentioning

confidence: 99%

mentioning

confidence: 99%

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Synthesis and photoreactivity of α-diketone-type precursors of acenes and their use in organic-device fabrication

Suzuki

Aotake

Yamaguchi

et al. 2014

Journal of Photochemistry and Photobiology C: Photochemistry Re

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“…Our approach employs α-diketone-type photoprecursors of acenes that can be converted to corresponding acenes by extrusion of CO molecules upon visible light irradiation14. We have previously shown that this type of photoprecursors can be employed in preparation of solution-processed organic field-effect transistors to yield good semiconducting performances comparable to those observed in vacuum-deposited films1516. Additionally, the quality of resulting films can be tuned by photoirradiation conditions such as intensity and duration16.…”

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confidence: 99%

Photoprecursor approach as an effective means for preparing multilayer organic semiconducting thin films by solution processes

Yamaguchi

Suzuki

Motoyama

et al. 2014

Sci Rep

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The vertical composition profile of active layer has a major effect on the performance of organic photovoltaic devices (OPVs). While stepwise deposition of different materials is a conceptually straightforward method for controlled preparation of multi-component active layers, it is practically challenging for solution processes because of dissolution of the lower layer. Herein, we overcome this difficulty by employing the photoprecursor approach, in which a soluble photoprecursor is solution-deposited then photoconverted in situ to a poorly soluble organic semiconductor. This approach enables solution-processing of the p-i-n triple-layer architecture that has been suggested to be effective in obtaining efficient OPVs. We show that, when 2,6-dithienylanthracene and a fullerene derivative PC71BM are used as donor and acceptor, respectively, the best p-i-n OPV affords a higher photovoltaic efficiency than the corresponding p-n device by 24% and bulk-heterojunction device by 67%. The photoprecursor approach is also applied to preparation of three-component p-i-n films containing another donor 2,6-bis(5′-(2-ethylhexyl)-(2,2′-bithiophen)-5-yl)anthracene in the i-layer to provide a nearly doubled efficiency as compared to the original two-component p-i-n system. These results indicate that the present approach can serve as an effective means for controlled preparation of well-performing multi-component active layers in OPVs and related organic electronic devices.

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A Soluble Dynamic Complex Strategy for the Solution‐Processed Fabrication of Organic Thin‐Film Transistors of a Boron‐Containing Polycyclic Aromatic Hydrocarbon

2016

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The solution‐processed fabrication of thin films of organic semiconductors enables the production of cost‐effective, large‐area organic electronic devices under mild conditions. The formation/dissociation of a dynamic B−N coordination bond can be used for the solution‐processed fabrication of semiconducting films of polycyclic aromatic hydrocarbon (PAH) materials. The poor solubility of a boron‐containing PAH in chloroform, toluene, and chlorobenzene was significantly improved by addition of minor amounts (1 wt % of solvent) of pyridine derivatives, as their coordination to the boron atom suppresses the inherent propensity of the PAHs to form π‐stacks. Spin‐coating solutions of the thus formed Lewis acid–base complexes resulted in the formation of amorphous thin films, which could be converted into polycrystalline films of the boron‐containing PAH upon thermal annealing. Organic thin‐film transistors prepared by this solution process displayed typical p‐type characteristics.

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FET performance and substitution effect on 2,6-dithienylanthracene devices prepared by photoirradiation of their diketone precursors

Cited by 20 publications

References 29 publications

Synthesis and photoreactivity of α-diketone-type precursors of acenes and their use in organic-device fabrication

Synthesis and photoreactivity of α-diketone-type precursors of acenes and their use in organic-device fabrication

Photoprecursor approach as an effective means for preparing multilayer organic semiconducting thin films by solution processes

A Soluble Dynamic Complex Strategy for the Solution‐Processed Fabrication of Organic Thin‐Film Transistors of a Boron‐Containing Polycyclic Aromatic Hydrocarbon

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