Solution-Processed Molecular Bis(Naphthalene Diimide) Derivatives with High Electron Mobility

Polander, Lauren E.; Tiwari, Shree Prakash; Pandey, Laxman; Seifried, Brian M.; Zhang, Qing; Barlow, Stephen; Risko, Chad; Brédas, Jean‐Luc; Kippelen, Bernard; Marder, Seth R.

doi:10.1021/cm201729s

Cited by 108 publications

(79 citation statements)

References 29 publications

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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%

“…While DTT has been extensively used in covalently linked donor-acceptor architectures [14,15,24], there is a single example charge-transfer (CT) complex with DTT as a donor and 7,7,8,8-tetracyanoquinodimethane (TCNQ) as an acceptor described in 1983 [27]. Here, we report the X-ray single crystal analysis of the DTT and its mixed-stack complexes with trimeric perfluoroo-phenylene mercury (I) (Chart 1), an acceptor known to form mixed-stack co-crystals with a variety of donors [28][29][30].…”

Section: Introductionmentioning

confidence: 99%

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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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Section: Introductionmentioning

confidence: 99%

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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“…Furthermore, delayed response times have been seen Naphthalene diimides (NDIs) are a class of compounds with high electron mobilities, and have primarily been used to produce air-stable n-type organic field effect transistors. [20][21][22] In addition, polymers developed from NDIs have shown promise as novel acceptors in organic solar cells, providing in excess of 1.5% device efficiencies, one of the highest for non-fullerene cells, with potential for extending device lifetimes. [23][24][25] The high electron mobilities of naphthalene diimides, coupled with their excellent air stability, give them considerable potential as air-stable electron injection layers.…”

Section: Introductionmentioning

confidence: 99%

“…These values are in good agreement with similarly structured NDI materials. [21,29] The deep HOMO value for DC18 ensures it will be an excellent hole-blocking material for many PLED polymers while facilitating electron injection. PLEDs were encapsulated prior to removal from the glovebox for testing in air.…”

Section: Introductionmentioning

confidence: 99%

Solution processed naphthalene diimide derivative as electron transport layers for enhanced brightness and efficient polymer light emitting diodes

et al. 2013

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Increasing the efficiency and lifetime of polymer light emitting diodes (PLEDs) requires a balanced injection and flow of charges through the device, driving demand for cheap and effective electron transport/ hole blocking layers. Some materials, such as conjugated polyelectrolytes, have been identified as potential candidates but the production of these materials requires complex, and hence costly, synthesis routes. We have utilized a soluble small molecule naphthalene diimide derivative (DC18) as a novel electron transport/hole blocking layer in common PLED architectures, and compared its electronic properties to those of the electron transport/hole blocking small molecule bathocuproine (BCP). PLEDs incorporating DC18 as the electron transport layer reduce turn on voltage by 25%; increase brightness over three and a half times; and provide a full five-fold enhancement in efficiencies compared to reference devices. While DC18 has similar properties to the effective conjugated polyelectrolytes used as electron transport layers, it is simpler to synthesise, reducing cost while retaining favourable electron transport properties, and improves upon their degree for efficiency enhancement. The impact on device lifetime is hypothosized to be significant as well, due to the air-stability seen in many naphthalene diimide derivatives.

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“…64 10 4 NTCDI-8 [102] 0. 65 10 8 NDI2-DTP [103] 1.5 -DFH4T [104] 0.06 10 5 DFHCO4T [105] 0.60 10 7 DFPCO4T [106] 0. 45 10 8 CuPcF 16 [52] 0.…”

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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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Solution-Processed Molecular Bis(Naphthalene Diimide) Derivatives with High Electron Mobility

Cited by 108 publications

References 29 publications

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

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

Solution processed naphthalene diimide derivative as electron transport layers for enhanced brightness and efficient polymer light emitting diodes

Recent Progress of Semiconductors in Organic Thin-Film Transistors

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