Electroluminescent Diodes from Complementary Discotic Benzoperylenes

Alibert-Fouet, Sonia; Dardel, Sébastien; Böck, Harald; Oukachmih, Mimoun; Archambeau, S.; Séguy, Isabelle; Jolinat, Pascale; Destruel, P.

doi:10.1002/cphc.200300734

Cited by 70 publications

(43 citation statements)

References 18 publications

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“…The temperature ranges of the mesophases remain large with short chains, illustrating that three short n-alkyl ester substituents are fully sufficient on coronene to induce hexagonal columnar liquid-crystalline self-assembly (Figure 1), in contrast to triesters with less disk-shaped aromatic cores, such as triphenylene or 5,6,11,12,17,21 and 22), in which only nematic, plastic crystalline or monotropic (metastable) columnar mesophases are observed. [4] Whereas the imides 11 and 17 with 4-heptyl side chains (obtained by imidification with 4-aminoheptane, the longest commercially available symmetrical secondary amine) do not melt at accessible temperatures, the imide-diesters 12 a (R = 4-heptyl, R' = n-propyl) and 12 b (R = 4-heptyl, R' = rac-2-ethylhexyl) show a crystal to mesophase transition at 197 and 60 8C, respectively.…”

Section: Resultsmentioning

confidence: 99%

“…[4,5] In particular, we have shown, in the case of benzoA C H T U N G T R E N N U N G [ghi]perylene 2 (Scheme 1), that the variation of the number and type (ester/imide) of carboxylic substituents alone permits the access to materials of strongly different electronic character, spanning from fairly strong acceptors to materials with donor-type behaviour. This allowed us to obtain p-n junction light-emitting diodes [5] and solar cells [6] by pairing electron-rich benzoA C…”

Section: Introductionmentioning

confidence: 99%

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Liquid‐Crystalline and Electron‐Deficient Coronene Oligocarboxylic Esters and Imides By Twofold Benzogenic Diels–Alder Reactions on Perylenes

Alibert-Fouet

Séguy

Bobo

et al. 2007

Chemistry A European J

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104

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Alkyl esters, imides and imido-esters of coronene-tri-, -tetra- and -octacarboxylic acids are accessible by a twofold oxidative benzogenic Diels-Alder reaction. Alkyl acrylates add to perylene, and maleic alkyl imides react twice with perylene as well as with perylene-tetracarboxylic tetraesters. Coronenes substituted with a greatly variable number of electron-withdrawing substituents are thus accessible, and di- and tetraimide derivatives are shown to be very pronounced electron-acceptor materials. The tri- and tetraalkyl esters and imidoesters self-assemble into columnar liquid-crystalline phases.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Liquid‐Crystalline and Electron‐Deficient Coronene Oligocarboxylic Esters and Imides By Twofold Benzogenic Diels–Alder Reactions on Perylenes

Alibert-Fouet

Séguy

Bobo

et al. 2007

Chemistry A European J

Self Cite

104

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“…Columnar LC diimide-diester compounds (27) are known to support electron transport in their mesophases because of the presence of strong electron-withdrawing substituents. By combining 27 with LC benzoperylenetriester compounds in bilayer, OLED device yielded red color emission [81]. Higher perylenediimides like terrylene and quaterrylenetetracarboxyldiimides exhibit columnar mesophases with attractive semiconducting properties [82].…”

Section: N-type Discotic Moleculesmentioning

confidence: 99%

Self-assembled 1D Semiconductors: Liquid Crystalline Columnar Phase

Mathews

Achalkumar

2015

Anisotropic Nanomaterials

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Organic semiconducting materials have emerged as potential alternative to inorganic silicon based semiconductors for the production of low-cost, flexible and light weight plastic electronic devices. When compared with crystalline and polymeric structures, liquid crystalline (LC) ordering in organic semiconductors favors their self-assembly into large area monodomain thin-film structures with carrier mobilities in the range from 10

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“…Columnar LC diimide-diester compounds (21) are known to support electron transport in their mesophases because of the presence of strong electron-withdrawing substituents. Combining 21 with LC benzoperylene triester compounds in bilayer OLED devices was reported to yield red color emission [77]. Higher homolog of perylene diimides, namely, terrylene and quaterrylene tetracarboxyldiimides, also exhibit columnar mesophase with attractive semiconducting properties [78].…”

Section: Discotic Liquid Crystals With High Charge-carrier Mobilitymentioning

confidence: 99%

Self‐Organized Discotic Liquid Crystals as Novel Organic Semiconductors

Mathews¹,

Li²

2011

Self‐Organized Organic Semiconductors

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Organic semiconductors are being intensely investigated and incorporated in device applications such as thin-film transistors, light-emitting diodes, solar cells, and sensors [1,2]. Organic molecules offer the advantage of low-cost synthesis and easy manufacture of large-area thin films by solution processing for the fabrication of a new generation of low-cost, lightweight, and flexible devices that would be inaccessible by conventional methods using inorganic semiconducting materials. The efficiency of these devices is directly related to the mobility of the charges achievable in the conducting layer fabricated by solution-processing techniques such as spin-coating, casting, or printing at ambient conditions exploitable on an industrial scale [3]. A number of different molecular and structural features (chemical purity, solubility, degree of crystallinity, energy band gap, absorption, emission, charge generation, and transport, etc.) have to be combined for optimizing device performance. On the basis of morphology of the materials in the active layers, they can be broadly classified into crystalline, amorphous, and liquid crystalline semiconductors. The highest charge-carrier mobilities (>2 cm 2 V −1 s −1 ) in organic systems have been measured in organic single crystals of pentacene and rubrene [4,5]. However, it is difficult to grow single-crystalline thin films. Charge mobilities in the polycrystalline films of polymeric semiconducting materials such as oligothiophenes, poly(phenylenevinylene), poly(thiophene), and poly(fluorine) compounds have reached values exceeding that of amorphous silicon (>1.0 cm 2 V −1 s −1 ) [6,7]. Thermal sublimation in vacuum is a common method for depositing polymeric

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Electroluminescent Diodes from Complementary Discotic Benzoperylenes

Cited by 70 publications

References 18 publications

Liquid‐Crystalline and Electron‐Deficient Coronene Oligocarboxylic Esters and Imides By Twofold Benzogenic Diels–Alder Reactions on Perylenes

Liquid‐Crystalline and Electron‐Deficient Coronene Oligocarboxylic Esters and Imides By Twofold Benzogenic Diels–Alder Reactions on Perylenes

Self-assembled 1D Semiconductors: Liquid Crystalline Columnar Phase

Self‐Organized Discotic Liquid Crystals as Novel Organic Semiconductors

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