278176-06-0Relevant articles and documents
Blue light material composed of acetylene bridged fluorene and anthracene derivatives and preparation method thereof
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Paragraph 0035; 0040-0042, (2020/03/29)
The invention belongs to the technical field of blue-light emitting material preparation, and discloses an acetylene bridged fluorene and anthracene derivative blue-light emitting material and a preparation method thereof. The method comprises the following steps: a compound intermediate product 2, a compound intermediate product 3, Pd(PPh3)2Cl2, CuI, PPh3 and a magnetic stirring bar are added into a single-necked flask with a volume of 250mL, and vacuumizing and nitrogen introducing are repeated for 4 times; under the protection of a nitrogen gas, a mixed solvent subjected to oxygen removal by introducing a nitrogen gas for 30min is added by a syringe, and a reaction is performed for 48h under a nitrogen gas atmosphere; the reaction is stopped, filtration is performed, filter residues arewashed for 3 times with toluene, a filtrate is separately washed twice with water and saturated brine, drying is performed by anhydrous sodium sulfate for overnight, and a solvent is evaporated to dryness to obtain a crude product; and the crude product is subjected to chromatography by applying a silica gel column, concentration is performed, the concentrated material is dropped into absolute methanol for recrystallization, and therefore the yellow solid is obtained. According to the invention, two n-octyl long aliphatic chains on fluorene can increase the solubility of the material in an organic solvent, and the acetylene linked fluorene and anthracene structure can increase the conjugacy and rigidity of the material.
Synthesis and photophysical properties of new perylene bisimide derivatives for application as emitting materials in OLEDs
Matussek, Marek,Filapek, Micha?,Gancarz, Pawe?,Krompiec, Stanis?aw,Grzegorz Ma?ecki, Jan,Kotowicz, Sonia,Siwy, Mariola,Ma?kowski, Sebastian,Chrobok, Anna,Schab-Balcerzak, Ewa,S?odek, Aneta
, p. 590 - 599 (2018/07/29)
Three novel perylene diimide derivatives with bulky aromatic moieties (fluorene, carbazolyl-fluorene, and anthracyl-fluorene) connected via triple bonds with perylene core were successfully designed and synthesized. The chemical structure of prepared compounds was confirmed by 1H and 13C NMR and mass spectrometry. Their optimized ground-state geometry and frontier molecular orbitals were theoretically estimated based on density functional theory. The compounds undergo the reversible electrochemical reduction process and exhibit very low energy band gaps (1.56–1.98 eV) being promising for electronic applications. They also display excellent solubility, high thermal stability and luminescence in solution and in the solid state as a film in the red spectral region. The highest photoluminescence quantum yield (79% in solution and 28% in the film) was found for perylene diimide bearing fluorene unit. All molecules showed the ability for light emission under an applied voltage. The fabricated diodes with structure ITO/PEDOT:PSS/compound/Al exhibited electroluminescence with maximum emission band located between 685 and 732 nm. The most intense electroluminescence, which was additionally plasmonically enhanced by incorporating silver nanowires, was observed for the device based on molecules with anthracene structure.
Meta - And para -Functionalized Thermally Crosslinkable OLED-Materials through Selective Transition-Metal-Catalyzed Cross-Coupling Reactions
Hempe, Matthias,Schnellb?cher, Lutz,Wiesner, Tobias,Reggelin, Michael
, p. 4489 - 4499 (2017/09/26)
Herein, a synthetic approach using selective transition-metal-catalyzed cross-coupling reactions to thermally crosslinkable OLED materials based on vinyl-functionalized arylamines is reported. In a modular approach, 9,9-dialkyl-2,7-diiodo-9 H -fluorene underwent a selective Ullmann cross-coupling reaction with bromo-substituted-diphenylamines to give 9,9-dialkyl-2,7-bis(bromo-substituted-diphenylamino)-9 H -fluorenes that underwent end-functionalization by the Suzuki-Miyaura reaction using potassium vinyltrifluoroborate to give the corresponding 9,9-dialkyl-2,7-bis(vinyl-substituted-diphenylamino)-9 H -fluorenes. Novel meta -functionalized materials were synthesized, which are difficult to prepare by traditional synthetic pathways. The thermal behavior of the compounds was investigated by DSC measurements, indicating a lower thermal sensitivity of the meta -substituted materials than their para -functionalized analogues.
