Organic electronic material containing phenanthrene and phenanthroline and application thereof
An organic electronic material, a technology of phenanthroline, which is applied in the field of organic electroluminescence, can solve the problems of low glass transition temperature of stability and affect the application of phenanthroline compounds, etc., to improve thermal stability and improve high luminous efficiency. , the effect of reducing power consumption
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Embodiment 1
[0046] Example 1 Synthesis of Compound 1
[0047]
[0048] 1. Synthesis of Intermediate 1-1
[0049] 2-chloro-9-iodo-10-phenylphenanthrene (10.0g, 24.12mmol), 4-cyanophenylboronic acid (5.3g, 36.07mmol) potassium carbonate (10.0g, 72.35mmol) were added to the there-necked flask, Then add toluene (100mL), ethanol (50mL) and deionized water (50mL), add Pd (PPh) under nitrogen protection 3 ) 2 Cl 2 (0.2g), refluxed for 12h, liquid separation, the organic phase was concentrated to about 30mL, stirred for crystallization, filtered, rinsed, and dried to obtain 7.4g of gray solid product with a yield of 79%. HRMS(ESI,m / z):[M+H] + calculated for C 27 H 16 ClN, 389.0971, found 389.0975.
[0050] 2. Synthesis of Intermediates 1-2
[0051]Intermediate 1-1 (7.0 g, 17.95 mmol), pinacol diboronate (5.47 g, 21.54 mmol), potassium acetate (5.29 g, 53.90 mmol) and anhydrous toluene (70 mL) were added to a three-necked flask under nitrogen. Pd(PPh3)2Cl2 (0.14g) was added under prote...
Embodiment 2
[0054] Synthesis of Example 2 Compounds
[0055]
[0056] 2-(4-Bromophenyl)-1,10-phenanthroline (0.5 g, 1.49 mmol), intermediate 1-2 (0.75 g, 1.58 mmol) and potassium carbonate (0.41 g, 2.97 mmol) were added to To the three-necked flask, add toluene (5mL), ethanol (2.5mL) and deionized water (2.5mL), add Pd (PPh) under nitrogen protection 3 ) 2 Cl 2 (0.01g), after refluxing for 8h, cooling and separating, the organic phase was concentrated to dryness, separated by column chromatography, DCM / CH 3 Elution with OH (10 / 1) gave 0.58 g of product in 63% yield. HRMS(ESI,m / z):[M+H] + calculated for C 45 H 28 N 3 ,610.2278,found 610.2279.Anal.:calcd:C,88.64;H,4.46;N,6.89;found:C,88.61;H,4.53;N,6.82.
Embodiment 3
[0057] Example 3 Synthesis of Compound 11
[0058]
[0059] 2-Bromo-1,10-phenanthroline (0.5g, 1.93mmol), intermediate 1-2 (0.98g, 2.04mmol) and potassium carbonate (0.53g, 3.83mmol) were added to a three-necked flask, followed by Toluene (5mL), ethanol (2.5mL) and deionized water (2.5mL), Pd (PPh) was added under nitrogen protection 3 ) 2 Cl 2 (0.01g), after refluxing for 8h, cooling and separating, the organic phase was concentrated to dryness, separated by column chromatography, DCM / CH 3 Elution with OH (10 / 1) gave 0.57 g of product in 55% yield. HRMS(ESI,m / z):[M+H] + calculated for C 39 H 24 N 3 ,534.1965,found534.1963.Anal.:calcd:C,87.78;H,4.34;N,7.87;found:C,87.73;H,4.41;N,7.81.
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