Bis(sulfonyl)biaryl derivatives as electron transporting and/or host materials
A technology of aryl and heteroaryl, applied in the field of bis(sulfonyl)diaryl derivatives as electron transport materials and/or host materials
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[0232] The various inventions described above are further illustrated by these following specific examples, which are not intended to be construed in any way as imposing limitations on the scope of the disclosure of the invention or the scope of the claims appended hereto. On the contrary, it will be clearly understood that various other embodiments, modifications, and equivalents thereof may be adopted, which, after reading the description herein, may suggest themselves to one of ordinary skill in the art without departing from the present invention. invention or the scope of these appended claims.
[0233] Starting materials were obtained from commercial sources and used without further purification. Electrochemical measurements were performed under nitrogen at about 10 -4 M of the analyte and 0.1 M tetra-n-butylammonium hexafluorophosphate in anhydrous deoxidized THF or DCM solution, the measurement uses a BAS potentiostat, a glassy carbon working electrode, a platinum aux...
example 1
[0248] Example 1-synthesis of 4,4'-bis(benzenesulfonyl)-1,1'-biphenyl, compound (1)
[0249] 4,4'-bis(benzenesulfonyl)-1,1'-biphenyl is a compound first reported by Holt and Jeffreys, J.Chem.Soc.[Chemical Society] 1965,773,4204-4205, Applicants have developed a higher throughput synthesis to produce quantities suitable for the device work described below.
[0250]
[0251] 4,4’-bis(phenylthio)biphenyl – Mix 3.99 mL of thiobenzene (39 mmol), 6.09 g of 4,4’-diiodobiphenyl (15 mmol), 4.56 g of K 2 CO 3 (33 mmol) and 71 mg of CuI (0.4 mmol) in DMF (10 mL) were placed in an oil bath preheated at 100 °C. The solution was stirred at 100 °C for 24 h. The solution was then cooled to room temperature and 10 mL of water was added. Use CH 2 Cl 2 (3mLx20mL) for extraction. Organic layer uses MgSO 4 Dry, filter and remove solvent under vacuum. The yellow solid was obtained by using hexane / CH 2 Cl 2 Purification was performed by chromatography with (8:2) as eluent to give a whi...
example 2
[0254] Example 2 - OLED device employing 4,4'-bis(benzenesulfonyl)-1,1'-biphenyl, (1) as host in emissive layer
[0255] Using 4,4'-bis(benzenesulfonyl)-1,1'-biphenyl, (1) as the host in the emission layer, the structure is ITO / PVK or CZ-I-25 / (1)-FIrpic / BCP / LiF / Al OLED devices were fabricated as follows. A glass / ITO / spin-coated PVK or CZ-I-25 substrate was loaded into a Kurt J. Lesker SPECTROS vacuum system not exposed to air, and then a sample of the sulfone compound (1) and 6wt% or 10wt% FIrpic at less than 1 x 10 -7 The thermal co-evaporation onto the substrate was carried out under the pressure of Torr to form an emissive layer with a thickness of 20 nm on the polycarbazole-coated ITO substrate. BCP (40 nm), LiF (2.5 nm) and Al (200 nm) were then coated by thermal vacuum deposition as electron transport / hole blocking, cathode and electrode layers, respectively.
[0256] The resulting device structure in image 3 shown in . The luminance-current-voltage (L-I-V) charac...
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