Benzimidazole-based electronic transmission compound
An electron transport, benzimidazole technology, applied in the field of organic electroluminescence, can solve the problems of affecting the life and efficiency of the device, low device efficiency, low electron mobility, etc.
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Embodiment 1
[0067] Synthesis of Compound 31
[0068]
[0069] Synthesis of Intermediate 31-1
[0070] In the flask, add thioxanthone (5.0g, 24mmol) and 45ml of acetic acid, heat to reflux, slowly add liquid bromine (9.6g, 60mmol), dropwise, heat to reflux for 12 hours, cool, filter to obtain 6.2g yellow Solid, 70% yield. 1 H NMR (400MHz, CDCl 3 ,δ):8.74(s,2H),7.73-7.75(d,J=8.4Hz,2H),7.46-7.48(d,J=8.4Hz,2H).
[0071] Synthesis of Intermediate 31-2 and Intermediate 31-3
[0072] In a three-necked flask, add magnesium chips (0.32g, 13.5mmol), add a catalytic amount of iodine, slowly drop 15ml of tetrahydrofuran (THF) solution dissolved in 2-bromobiphenyl (3g, 13.5mmol), and heat to reflux for 2 hours , cooling, the resulting liquid was slowly added dropwise to 30ml tetrahydrofuran solution in which intermediate 31-1 (2.5g, 6.8mmol) was dissolved, the dropwise addition was completed, refluxed for 6 hours, cooled, the reaction solution was poured into water, and washed with ethyl acetat...
Embodiment 2
[0077] Synthesis of compound 51
[0078]
[0079] In a one-necked flask, add compound 31-3 (0.25g, 0.5mmol), 3-(1-phenyl-1H-benzimidazol-2-yl) phenylboronic acid (0.4g, 1.24mmol), 20ml of THF and 8ml of 2M K 2 CO 3 Aqueous solution, under the protection of nitrogen, add 10mg tetrakis (triphenylphosphine) palladium (0.0075mmol), then heat and reflux for 5 hours, after the reaction is completed, cool, extract three times with dichloromethane, dry the organic layer with anhydrous sodium sulfate, and rotate The organic solvent was removed, and the crude product was purified by column chromatography to obtain 0.31 g of off-white solid with a yield of 70%. 1 H NMR (400MHz, CDCl 3 ,δ):7.86-7.88(d,J=7.6Hz,2H),7.77-7.79(d,J=7.6Hz,2H),7.60-7.62(d,J=7.6Hz,2H),7.16-7.51( m,28H),7.07-7.10(m,4H),6.70(s,2H).
[0080] The proton magnetic spectrum of compound 51 is shown in figure 2 . Compound 51 at a concentration of 1×10-5 The maximum absorption wavelength measured by a Varian Car...
Embodiment 3
[0082] Fabrication of Organic Electroluminescent Devices
[0083] Preparation of OLED using compound 51 of Example 2
[0084] First, the transparent conductive ITO glass substrate 110 (with anode 120 on it) (China CSG Group Co., Ltd.) is washed in sequence with deionized water, ethanol, acetone and deionized water, and then treated with oxygen plasma for 30 seconds.
[0085] Then, NPB was evaporated to form a hole transport layer 130 with a thickness of 60 nm.
[0086] Then, a 30nm thick compound Alq was evaporated on the hole transport layer 3 as the light emitting layer 140 .
[0087] Then, compound 51 was evaporated to a thickness of 20 nm as the electron transport layer 150 on the light emitting layer.
[0088] Finally, 1nm LiF was vapor-deposited as the electron injection layer 160 and 100nm Al as the cathode 170 of the device.
[0089] The prepared device (the schematic diagram of the structure is shown in Figure 5 ) Measured at 25mA / cm with Photo Research PR650 sp...
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