Organic semiconductor hole transport material
A hole transport material, organic semiconductor technology, applied in the fields of semiconductor devices, semiconductor/solid-state device manufacturing, organic chemistry, etc., can solve the problems of difficult film formation, poor solubility, etc., and achieve the effect of high temperature working life and low voltage
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Embodiment 1
[0047] Synthesis of compound (1):
[0048] .
[0049] (1) Synthesis of TM1: Weigh 3.5 grams of (4-bromophenyl) aniline, 4.9 grams of boric acid in a 500ml three-necked flask, add 9.2 grams of potassium phosphate, 0.35 grams of S-Phos, 0.26 grams of Pd2(dba)3, Measure 200 mL of toluene and 20 mL of distilled water with a graduated cylinder, start stirring, vacuumize, replace with nitrogen, raise the temperature to boiling, reflux and stir for 16 h under the protection of nitrogen, stop the reaction, separate the liquid with a separatory funnel, and collect the organic phase. The solvent was distilled off under reduced pressure to obtain a crude product, which was separated and purified by silica gel column chromatography using n-hexane: dichloromethane = 4:1 as the eluent to obtain 7.5 g of a white solid with a yield of 80%.
[0050] (2) Synthesis of compound (1): Weigh 0.9 g of TM1, 0.35 g of 2,7-dibromo-9,9 dimethylfluorene in a 50 ml two-necked bottle, add 0.1 g of Pd2(db...
Embodiment 2
[0052] Synthesis of compound (2):
[0053] .
[0054] Weigh 0.9 g of TM1, 0.4 g of 3,6-dibromo-9-phenylcarbazole in a 50 ml two-necked bottle, add 0.1 g of Pd2(dba)3, 0.15 g of tri-tert-butylphosphine, and 0.6 g of tert-butanol Sodium, use a measuring cylinder to measure 10mL of anhydrous toluene, vacuumize, nitrogen protection, raise the temperature to 90° and stir for 16h, stop the reaction and distill off the solvent under reduced pressure to obtain the crude product, then separate and purify through silica gel column chromatography, and use n-hexane as the eluent : DCM=3:1, 0.7 g of light yellow compound (2) was obtained, yield: 65%.
Embodiment 3
[0056] Device application example: in a background vacuum up to 10 -5 Pa's multi-source evaporation OLED preparation equipment adopts the following device structure: ITO / mTDATA (100 ?) / HTL (400 ?) / CBP:Ir(ppy)3 9% (300 ?) / TPBi (300 ?) / LiF(10 ?) / Al, using different HTL OLED light-emitting devices for comparison. Wherein the vacuum deposition speed of each organic layer and electrode is listed in Table 1 at time.
[0057] Table 1: Fabrication conditions of phosphorescent OLED devices (doping wt concentration in the emitting layer is 9%).
[0058]
[0059] Table 2: OLED green device performance (9000 Cd / cm 2 illuminance).
[0060]
[0061] Compared with the known hole-transporting material NPB, Table 2 shows that the compounds (1) and (2) of the present invention as examples of green doped light-emitting OLEDs can significantly reduce the working voltage and improve the device life LT 50% effect.
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