Benzimidazole diphosphine Cu (I) complex and preparation method thereof

Abstract

The invention belongs to the technical field of synthesis of organic complexes, and particularly relates to a benzimidazole diphosphine Cu (I) complex and a preparation method thereof. The molecular formula of the benzimidazole diphosphine Cu (I) complex is C56H40N4P2Cu2I2, and the structural formula of the benzimidazole diphosphine Cu (I) complex is shown as a formula I in the specification. In the ultraviolet-visible absorption spectrum of the benzimidazole diphosphine Cu (I) complex provided by the invention, strong absorption (wherein epsilon is greater than 5*10<4> L / mol / cm) near a wavelength of 230 nm, medium-intensity absorption occurs in a wavelength range of 300-320 nm, the maximum excitation wavelength is 376 nm, the maximum emission wavelength of 609 nm, and efficient orange luminescence is shown; and the solid powder of the complex has luminescent quantum efficiency (PLQYs) of 45% at 293K and luminescent lifetime of 2.26 microseconds, so the complex is an excellent OLED photoluminescent material.

Description

technical field

[0001] The invention belongs to the technical field of organic complex synthesis, and in particular relates to a benzimidazole bisphosphine Cu(I) complex and a preparation method thereof. Background technique

[0002] With the continuous development of society and science and technology, luminescent materials have become one of the most active topics in the field of materials research. There are many types of luminescent materials, which can be classified into photoluminescence, electroluminescence, bioluminescence, and chemiluminescence according to the source of luminescence energy. Among various types of luminescence, electroluminescent devices are constantly being researched and explored. Due to its excellent characteristics such as ultra-thin, low power consumption, high contrast, natural color, flexible display, etc., organic electroluminescent devices (OLEDs) are becoming the mainstream trend of energy-saving lighting and new display technologies, and...

Examples

Embodiment 1

[0051](1) Add aniline (3.3mL, 36.2mmol), 2,6-difluoronitrobenzene (3mL, 30mmol) and anhydrous potassium fluoride (1.8g, 30mmol) into 9mL dimethyl sulfoxide, stir After the dissolution is complete, react at 95°C for 15 hours; after the reaction is completed, cool the system to room temperature, then add 30 mL of distilled water to the reaction system, stir until a large amount of red precipitate appears, filter the precipitate and wash 3 times with 30 ml (10 ml×3 times) of distilled water, The solid was filtered out and dried in a drying oven to obtain intermediate product A;

[0052] (2) Intermediate product A (7g, 20mmol) and m-phthalaldehyde (1.34g, 10mmol) obtained in step (1) are added in 120ml mixed solvent (volume ratio of ethanol and water is 5:1), stir Dissolve, then add sodium dithionite (20g, 120mmol), reflux at 125°C for 8h; after the reaction is complete, cool the system to room temperature, recover the ethanol in the system by rotary evaporation, then extract with...

Embodiment 2

[0056] (1) Add aniline (3.3mL, 36.2mmol), 2,6-difluoronitrobenzene (3mL, 30mmol) and anhydrous potassium fluoride (1.8g, 30mmol) into 9mL dimethyl sulfoxide, stir After the dissolution is complete, react at 100°C for 12 hours; after the reaction is completed, cool the system to room temperature, then add 30 mL of distilled water to the reaction system, stir until a large amount of red precipitate appears, filter the precipitate and wash 3 times with 30 ml (10 ml×3 times) of distilled water, The solid was filtered out and dried in a drying oven to obtain intermediate product A;

[0057] (2) Intermediate product A (7g, 20mmol) and m-phthalaldehyde (1.34g, 10mmol) obtained in step (1) are added in 120ml mixed solvent (volume ratio of ethanol and water is 5:1), stir Dissolve, then add sodium dithionite (20g, 120mmol), reflux at 130°C for 6h; after the reaction is complete, cool the system to room temperature, recover the ethanol in the system by rotary evaporation, then extract wi...

Embodiment 3

[0061] (1) Add aniline (3.3mL, 36.2mmol), 2,6-difluoronitrobenzene (3mL, 30mmol) and anhydrous potassium fluoride (1.8g, 30mmol) into 9mL dimethyl sulfoxide, stir After the dissolution is complete, react at 98°C for 14 hours; after the reaction is completed, cool the system to room temperature, then add 30 mL of distilled water to the reaction system, stir until a large amount of red precipitate appears, filter the precipitate and wash 3 times with 30 ml (10 ml×3 times) of distilled water, The solid was filtered out and dried in a drying oven to obtain intermediate product A;

[0062] (2) Intermediate product A (7g, 20mmol) and m-phthalaldehyde (1.34g, 10mmol) obtained in step (1) are added in 120ml mixed solvent (volume ratio of ethanol and water is 5:1), stir Dissolved, then added sodium dithionite (20g, 120mmol), and refluxed at 128°C for 7h; after the reaction was completed, the system was cooled to room temperature, and the ethanol in the system was recovered by rotary ev...

technical field

[0001] The invention belongs to the technical field of organic complex synthesis, and in particular relates to a benzimidazole bisphosphine Cu(I) complex and a preparation method thereof. Background technique

[0002] With the continuous development of society and science and technology, luminescent materials have become one of the most active topics in the field of materials research. There are many types of luminescent materials, which can be classified into photoluminescence, electroluminescence, bioluminescence, and chemiluminescence according to the source of luminescence energy. Among various types of luminescence, electroluminescent devices are constantly being researched and explored. Due to its excellent characteristics such as ultra-thin, low power consumption, high contrast, natural color, flexible display, etc., organic electroluminescent devices (OLEDs) are becoming the mainstream trend of energy-saving lighting and new display technologies, and...

Examples

Embodiment 1

[0051](1) Add aniline (3.3mL, 36.2mmol), 2,6-difluoronitrobenzene (3mL, 30mmol) and anhydrous potassium fluoride (1.8g, 30mmol) into 9mL dimethyl sulfoxide, stir After the dissolution is complete, react at 95°C for 15 hours; after the reaction is completed, cool the system to room temperature, then add 30 mL of distilled water to the reaction system, stir until a large amount of red precipitate appears, filter the precipitate and wash 3 times with 30 ml (10 ml×3 times) of distilled water, The solid was filtered out and dried in a drying oven to obtain intermediate product A;

[0052] (2) Intermediate product A (7g, 20mmol) and m-phthalaldehyde (1.34g, 10mmol) obtained in step (1) are added in 120ml mixed solvent (volume ratio of ethanol and water is 5:1), stir Dissolve, then add sodium dithionite (20g, 120mmol), reflux at 125°C for 8h; after the reaction is complete, cool the system to room temperature, recover the ethanol in the system by rotary evaporation, then extract with...

Embodiment 2

[0056] (1) Add aniline (3.3mL, 36.2mmol), 2,6-difluoronitrobenzene (3mL, 30mmol) and anhydrous potassium fluoride (1.8g, 30mmol) into 9mL dimethyl sulfoxide, stir After the dissolution is complete, react at 100°C for 12 hours; after the reaction is completed, cool the system to room temperature, then add 30 mL of distilled water to the reaction system, stir until a large amount of red precipitate appears, filter the precipitate and wash 3 times with 30 ml (10 ml×3 times) of distilled water, The solid was filtered out and dried in a drying oven to obtain intermediate product A;

[0057] (2) Intermediate product A (7g, 20mmol) and m-phthalaldehyde (1.34g, 10mmol) obtained in step (1) are added in 120ml mixed solvent (volume ratio of ethanol and water is 5:1), stir Dissolve, then add sodium dithionite (20g, 120mmol), reflux at 130°C for 6h; after the reaction is complete, cool the system to room temperature, recover the ethanol in the system by rotary evaporation, then extract wi...

Embodiment 3

[0061] (1) Add aniline (3.3mL, 36.2mmol), 2,6-difluoronitrobenzene (3mL, 30mmol) and anhydrous potassium fluoride (1.8g, 30mmol) into 9mL dimethyl sulfoxide, stir After the dissolution is complete, react at 98°C for 14 hours; after the reaction is completed, cool the system to room temperature, then add 30 mL of distilled water to the reaction system, stir until a large amount of red precipitate appears, filter the precipitate and wash 3 times with 30 ml (10 ml×3 times) of distilled water, The solid was filtered out and dried in a drying oven to obtain intermediate product A;

[0062] (2) Intermediate product A (7g, 20mmol) and m-phthalaldehyde (1.34g, 10mmol) obtained in step (1) are added in 120ml mixed solvent (volume ratio of ethanol and water is 5:1), stir Dissolved, then added sodium dithionite (20g, 120mmol), and refluxed at 128°C for 7h; after the reaction was completed, the system was cooled to room temperature, and the ethanol in the system was recovered by rotary ev...

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