Nitrogen-containing compound, electronic component comprising same, and electronic device
A technology for nitrogen compounds and electronic components is applied in the fields of nitrogen-containing compounds and electronic components and electronic devices containing them, and achieves the effects of good film-forming properties, not easy to crystallize, and long life.
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preparation example 1
[0129] Preparation Example 1: Synthesis of Compound 8
[0130]
[0131] Intermediate IM-A-1 (15.0g, 27.1mmol), 9,10-dihydro-9,9-dimethylacridine (6.2g, 29.8mmol), Pd 2 (dba) 3 (0.2g, 0.3mmol), tri-tert-butylphosphine (0.1g, 0.5mmol), sodium tert-butoxide (3.9g, 40.7mmol), and toluene (150mL) were added to a three-necked flask, and the temperature was raised to 110°C under nitrogen protection. Heat to reflux and stir for 5h, cool to room temperature, add toluene and extract the reaction solution, combine the organic phases, dry the organic layer with anhydrous magnesium sulfate, filter, and concentrate; use silica gel column chromatography (dichloromethane / n-heptane) to purify to obtain a solid Compound 8 (11.8 g, yield 64%). m S [M+H] + = 681.29.
[0132] The compounds shown in Table 1 below were synthesized in a similar manner to Preparation Example 1, except that starting material 1 was used instead of 9,10-dihydro-9,9-dimethylacridine.
[0133] Table 1
[0134] ...
preparation example 11
[0144] Preparation Example 11: Synthesis of Compound 38
[0145]
[0146] Intermediate IM-A-1 (12.0g, 21.7mmol), intermediate IM-B-1 (8.5g, 26.0mmol), tetrakis triphenylphosphine palladium (1.2g, 1.0mmol), potassium carbonate (6.0g , 43.4mmol), tetrabutylammonium bromide (0.1g, 0.4mmol), toluene (100mL), ethanol (50mL) and deionized water (25mL) were added into a three-necked flask, and the temperature was raised to 75-80°C under nitrogen protection, Heated to reflux and stirred to react for 8h, the solution was cooled to room temperature, added toluene to extract the reaction solution, combined the organic phases, dried the organic layer with anhydrous magnesium sulfate, filtered, and concentrated; purified by silica gel column chromatography to obtain solid compound 38 (10.6g, yield 65%).
[0147] The compounds shown in Table 3 below were prepared in the same manner as in Preparation Example 11, except that the following intermediate IM-B-2 to intermediate IM-B-10 were u...
preparation example 21
[0151] Preparation 21: Synthesis of Compound 48
[0152]
[0153] 9,9-bis(4-bromophenyl)-9H-fluorene (30.0g, 62.9mmol), 9,9-dimethylacridine (11.8g, 56.6mmol), Pd 2 (dba) 3 (0.5g, 0.6mmol), x-phos (0.6g, 1.2mmol), sodium tert-butoxide (12.1g, 125.9mmol), and toluene (300mL) were added into a three-necked flask, heated to 110°C under nitrogen protection, and heated to reflux Stir the reaction for 6 hours, cool the solution to room temperature, add toluene to extract the reaction solution, combine the organic phases, dry the organic layer with anhydrous magnesium sulfate, filter, and concentrate; use silica gel column chromatography (dichloromethane / n-heptane) for purification to obtain a solid compound Intermediate IM-C-I-1 (19.7 g, 52% yield).
[0154] The intermediate IM-C-I-1 (19.0g, 31.4mmol), biboronic acid pinacol ester (11.9g, 47.1mmol), Pd(dppf)Cl 2 (0.4g, 0.6mmol), KOAc (6.1g, 62.8mmol), add 1,4-dioxane (100mL) and reflux at 100°C for 12h, using CH 2 Cl 2 and w...
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