Bipolar red light-phosphorescent light main material and preparation method thereof as well as organic electroluminescence device
A phosphorescent main body and bipolar technology, which is applied in the direction of luminescent materials, electric solid-state devices, semiconductor devices, etc., can solve the problems that are not conducive to carrier injection and transport balance, low glass transition temperature, and lack of main materials, etc., to achieve Simple synthetic route, good thermal stability, reducing the effect of process flow
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Embodiment 1
[0030] Example 1: The bipolar red phosphorescent host material of this example has a structure of 1,5-diphenyl-1,5-bis(4-(benzenesulfonyl)phenyl)-1,5-bis Hydrocyclopenta[def]fluorene, the preparation steps are as follows:
[0031]
[0032] Step 1: Dissolve 1,5-bis(4-bromophenyl)-1,5-diphenyl-1,5-dihydrocyclopenta[def]fluorene (51.2g, 80mmol) under nitrogen protection In 200mL N,N-dimethylformamide (DMF) solution, then add thiophenol (17.6g, 160mmol), potassium carbonate (22.1g, 160mmol), cuprous iodide (1.52g, 8mmol). The mixture was stirred and reacted at 120°C for 6 hours. The reaction was stopped and cooled to room temperature, filtered, and the solid was washed three times with distilled water. The solid compound was then separated by silica gel column chromatography using n-hexane as the eluent to obtain product C as an off-white solid. The yield was 92%.
[0033] The second step: under ice bath, dissolve C (27.9g, 40mmol) in 120mL of dichloromethane (DCM) solution,...
Embodiment 2
[0035] Example 2: The bipolar red phosphorescent host material of this example has the structure: 1,5-diphenyl-1,5-bis(4-(benzenesulfonyl)phenyl)-1,5- Dihydrocyclopenta[def]fluorene, the preparation steps are as follows:
[0036]
[0037] Step 1: Dissolve 1,5-bis(4-bromophenyl)-1,5-diphenyl-1,5-dihydrocyclopenta[def]fluorene (51.2g, 80mmol) under nitrogen protection In 200mL of toluene (Tol) solution, then add thiophenol (19.4g, 176mmol), cesium carbonate (57.2g, 176mmol), copper powder (0.768g, 12mmol). The mixture was stirred and reacted at 110°C for 9 hours. The reaction was stopped and cooled to room temperature, filtered, and the solid was washed three times with distilled water. The solid compound was then separated by silica gel column chromatography using n-hexane as the eluent to obtain product C as an off-white solid. The yield was 90%.
[0038] The second step: the step is the same as the second step in Example 1.
Embodiment 3
[0039] Embodiment 3: The bipolar red phosphorescence host material of this embodiment has the structure: 1,5-diphenyl-1,5-bis(4-(benzenesulfonyl)phenyl)-1,5- Dihydrocyclopenta[def]fluorene, the preparation steps are as follows:
[0040]
[0041] Step 1: Dissolve 1,5-bis(4-bromophenyl)-1,5-diphenyl-1,5-dihydrocyclopenta[def]fluorene (51.2g, 80mmol) under nitrogen protection In 200 mL of acetonitrile (MeCN) solution, thiophenol (21.1 g, 192 mmol), potassium phosphate (39 g, 184 mmol), and cuprous oxide (2.3 g, 16 mmol) were added. The mixture was stirred and reacted at 90°C for 12 hours. The reaction was stopped and cooled to room temperature, filtered, and the solid was washed three times with distilled water. The solid compound was then separated by silica gel column chromatography using n-hexane as the eluent to obtain product C as an off-white solid. The yield was 94%.
[0042] The second step: the step is the same as the second step in Example 1.
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