Preparation and application of thermal activation delayed fluorescence OLED material based on seven-membered ring diimide receptor
A thermally activated delayed, cyclic diimide technology, applied in the fields of luminescent materials, semiconductor/solid-state device manufacturing, photovoltaic power generation, etc., can solve the problems of single species, low device efficiency, limiting the development of efficient delayed fluorescent materials, etc. The effect of application effect, good performance and good industrialization prospect
- Summary
- Abstract
- Description
- Claims
- Application Information
AI Technical Summary
Problems solved by technology
Method used
Image
Examples
Embodiment 1
[0042] Preparation of Intermediate B1
[0043]
[0044] Put a magnetic stirring bar in a 250mL three-necked flask, add p-bromobenzoic acid (10g, 50mmol), ruthenium(II) chloride (518.6mg, 2.5mmol), 1,8-diazabicyclo[5.4.0 ] undec-7-ene (7.2mL, 50mmol), replace oxygen more than three times, add ethylene glycol dimethyl ether 60mL, heat up to 110°C and react for 30 hours. After the reaction was completed and cooled to room temperature, potassium carbonate (20.7g, 150mmol) and methyl iodide (9.5mL, 150mmol) were added, stirred at room temperature for 4 hours, filtered under reduced pressure, the solvent and low boilers were evaporated in vacuo, and the crude product was passed through the column Chromatographic purification, the eluent is petroleum ether: ethyl acetate = 10:1. The target intermediate B1 was obtained, 5.56 g of white solid, and the yield was 52%.
[0045] High resolution mass spectrometry, ESI source, positive ion mode, molecular formula [C 16 h 12 Br 2 o 4...
Embodiment 2
[0061] Preparation of Intermediate D1
[0062]
[0063] Put a magnetic stirring bar in a 250mL three-necked flask, add p-bromobenzoic acid (10g, 50mmol), benzoic acid (1.525g, 12.5mmol), dichloro(p-methylcumene) ruthenium (II) dimer (736mg, 1.25mmol), copper oxide (1.5g, 18.75mmol), 1,8-diazabicyclo[5.4.0]undec-7-ene (9.0mL, 62.5mmol), replace oxygen more than three times , add 60 mL of anhydrous 1,4-dioxane, raise the temperature to 110° C. and react for 30 hours. After the reaction was completed and cooled to room temperature, potassium carbonate (8.625g, 62.5mmol) and methyl iodide (3.96mL, 62.5mmol) were added, stirred at room temperature for 4 hours, filtered under reduced pressure, the solvent and low boilers were evaporated in vacuo, and the crude product Purified by column chromatography, the eluent is petroleum ether: ethyl acetate = 10:1. The target intermediate D1 was obtained as a white solid of 1.74 g with a yield of 40%.
[0064] High resolution mass spectr...
Embodiment 3
[0080] The preparation of compound C33 is similar to the preparation of compound C1, except that 4-(9,9-dimethyl-9,10-dihydroacridine)phenylboronic acid is used instead of 9,10-dihydro-9,9-di Methylacridine, intermediate E2 was prepared, and compound C33 was prepared as light yellow solid with a total yield of 37%.
[0081] High resolution mass spectrometry, ESI source, positive ion mode, molecular formula [C 66 h 55 N 3 o 2 +Na] + , the theoretical value is 944.4186, and the measured value is 944.4182.
[0082] Preparation of Intermediate E2
[0083]
[0084] A magnetic stirrer was placed in a 25mL high-pressure tube, and intermediate B1 (214mg, 0.5mmol), 4-(9,9-dimethyl-9,10-dihydroacridine) phenylboronic acid (362mg, 1.1mmol) was added, Tetrakis(triphenylphosphine)palladium (57.8mg, 0.05mmol), potassium carbonate (276mg, 2.0mmol), nitrogen was replaced three times or more, 5.0mL of degassed tetrahydrofuran was added, and the reaction was refluxed for 24 hours. Aft...
PUM
Login to View More Abstract
Description
Claims
Application Information
Login to View More