Tetraaryl pyrenes: photophysical properties, computational studies, crystal structures, and application in OLEDs

El‐Assaad, Tarek H.; Auer, Manuel; Castañeda, Raúl; Hallal, Kassem M.; Jradi, Fadi M.; Mosca, Lorenzo; Khnayzer, Rony S.; Patra, Digambara; Timofeeva, Tatiana V.; Brédas, Jean‐Luc; List‐Kratochvil, Emil J. W.; Wex, Brigitte; Kaafarani, Bilal R.

doi:10.1039/c5tc02849c

Cited by 38 publications

(29 citation statements)

References 74 publications

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“…The crystal structures of non-fluorinated analogues of compounds 1 and 3 are not known but these values are in the usual range for Ph-substituted pyrenes. 17 In spite of the similarity of the molecules, the packing motifs in crystals 1 and 3 are quite different. No apparent π...π interactions are present in structure 1 and the pair-wise energy calculations 18 show almost isotropic distribution of the strongest intermolecular interactions in the structure of 1.…”

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confidence: 99%

Synthesis of Fluoro and Cyanoaryl‐Containing Pyrene Derivatives and their Optical and Electrochemical Properties

et al. 2019

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Mono-and 1,6-disubstituted pyrene derivatives bearing perfluorotoluene or perfluorobenzonitrile moieties were synthesized by nucleophilic substitution processes. The compounds were characterized by NMR, UV-vis, photoluminescence (PL), thermal gravimetric analysis (TGA), differential scanning calorimetry (DSC), cyclic voltametry (CV) and density functional theory (DFT) calculations. We found that derivatives substituted with perfluorobenzonitrile showed better thermal stability, stronger electron withdrawing ability and better fluorescence properties than the corresponding perfluorotoluyl-pyrene systems Results and Discussion Synthesis Several pyrene derivatives bearing polyfluoroaryl substituents were synthesized by following the strategy shown in Scheme 1. Key starting material 1-bromopyrene was prepared by reaction of HBr with a peroxide initiator. After 15 h, GC-MS revealed that the reaction mixture contained 82% monobrominated compound and 16% dibrominated compound, which was sufficient for work

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Section: Full Papermentioning

confidence: 99%

Synthesis of Fluoro and Cyanoaryl‐Containing Pyrene Derivatives and their Optical and Electrochemical Properties

et al. 2019

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“…In a first series, the central pyrenyl core is directly linked to four donor groups: 4‐phenoxyphenyl in 22 , 3,4,5‐trimethoxyphenyl in 23 , 4‐(methyl‐thio)phenyl in 24 (Figure 3). [ 54 ] TE‐SL 22 and TE‐SL 23 present interesting performances. These devices emit sky‐blue light (CIE: 0.16, 0.2 and 0.15, 0.24, respectively) since 2.8/2.9 V and CE max reach 2.0 and 2.6 cd A −1 respectively.…”

Section: Oscs Constructed On the Association Of A π‐Conjugated Core Amentioning

confidence: 99%

“…Several pyrene‐based dendrimers with different peripheral chromophores have also been incorporated in SL‐OLEDs. For example, in 57 , the central pyrenyl core is linked to four 3,5‐bis(trifluoromethyl)‐phenyl units, [ 54 ] whereas it is linked to eight oxadiazole cores thanks to well suited oligophenyl links in 58 [ 55 ] and 59 [ 77 ] (Figure 8, left).…”

Section: Oscs Constructed On the Association Of A π‐Conjugated Core Amentioning

confidence: 99%

“…The EL properties of these OSCs were investigated in either TE‐SL 57 , [ 54 ] SP‐SL 58, [ 55 ] or SP‐SL 59 . [ 77 ] The device performances are low with CE max only reaching 0.004 cd A −1 (TE‐SL 57 ), 0.04 cd A −1 (SP‐SL 59 [ 77 ] ) or 0.14 cd A −1 (SP‐SL 58 [ 55 ] ) despite low LUMO levels (−2.86 eV for 57 , −2.46 eV for 58, and −2.52 eV for 59 ).…”

Section: Oscs Constructed On the Association Of A π‐Conjugated Core Amentioning

confidence: 99%

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Blue Single‐Layer Organic Light‐Emitting Diodes Using Fluorescent Materials: A Molecular Design View Point

Poriel

Rault‐Berthelot

2020

Adv Funct Materials

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technology is mastered, it suffers from a real complexity, a high cost, and is time-consuming. Simplifying the multilayer structure with the so-called single-layer OLEDs (SL-OLEDs), the simplest device only made of the electrodes and the EML has hence rapidly appeared as a promising and appealing solution in this technology (Scheme 2, left).However, removing the functional organic layers of an OLED stack often leads to a dramatic decrease of the performance and reaching high efficiency blue SL-OLEDs has required intense researches and especially in term of materials design. Indeed, if one removes all the organic layers surrounding the EML, the efficient injection, transport, and recombination of charges within the device, should be insured by the EML itself and therefore the fluorophore. However, this appears to be a real obstacle to cross for blue emitting materials. Indeed, blue fluorophores usually possess a high HOMO and a low LUMO energy rendering the injection of charges in such materials very difficult. This has been one of the main issue to address in this field. Common properties required for high-performance blue emitting materials can be summarized as follows: 1) blue light emission between 380 and 500 nm with maximum wavelength around 450 nm; 2) a narrow full width at half maximum less than 60 nm; which produces low Commission Internationale de l'Eclairage (CIE) y-coordinate of less than 0.10 for TVs and cell phones; 3) thermal and morphological stability for stable device operation and a long device lifetime; 4) balance charge transport between electrons and holes flow and 5) adequate HOMO/LUMO energy levels for charge recombination and injection.Gathering all these properties in a single molecule is far from being an easy task and requires very precise designs. Indeed, as soon as one tries to adjust the HOMO/ LUMO energy levels of an organic semiconductor (OSC) with the Fermi levels of OLED electrodes, its gap is contracted and the emission wavelength is bathochromically shifted. This design strategy can hence lead to a material in which the charges can be more easily injected (the gap is contracted) but with an emission wavelength no more in the blue region. Trying to find the best compromise between adequate HOMO/LUMO energy and a blue emission has been the main challenge to address in the molecular design of efficient fluorophores for blue SL-OLEDs. This particularity has strongly restrained the development of such materials. However, for the last 30 years, research groups have developed many different molecular design strategies, which have led in some cases to high performance blue SL-OLEDs. Reaching high performance SL-OLEDs by molecular engineering of the fluorophore and Cyril Poriel is

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“…1 These properties can be tailored to meet specic requirements through modications of its chemical structure; [2][3][4][5][6][7][8][9][10][11] therefore, pyrene derivatives are recognized as promising materials for organic light-emitting devices. [12][13][14][15][16][17][18][19][20][21][22][23][24][25] Pyrene is also well known for the formation of an excimer. [26][27][28][29] An aromatic excimer is a dimeric complex of the same aromatic molecules that is formed in the excited state.…”

Section: Introductionmentioning

confidence: 99%

Ab initio study on the excited states of pyrene and its derivatives using multi-reference perturbation theory methods

Shirai

Inagaki

2020

RSC Adv.

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Tetraaryl pyrenes: photophysical properties, computational studies, crystal structures, and application in OLEDs

Abstract: Nine 1,3,6,8-tetraarylpyrenes were prepared and characterized for OLED-based blue-light emission.

Cited by 38 publications

References 74 publications

Synthesis of Fluoro and Cyanoaryl‐Containing Pyrene Derivatives and their Optical and Electrochemical Properties

Synthesis of Fluoro and Cyanoaryl‐Containing Pyrene Derivatives and their Optical and Electrochemical Properties

Blue Single‐Layer Organic Light‐Emitting Diodes Using Fluorescent Materials: A Molecular Design View Point

Ab initio study on the excited states of pyrene and its derivatives using multi-reference perturbation theory methods

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