A kind of benzimidazole bisphosphine cu (i) complex and preparation method thereof

Abstract

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. The molecular formula of the described benzimidazole bisphosphine Cu(I) complex is C 56 h 40 N 4 P 2 Cu 2 I 2 , whose structural formula is shown in Formula I. In the ultraviolet-visible absorption spectrum of the benzimidazole bisphosphine Cu(I) complex provided by the invention, there is strong absorption (ε>5×10) near 230nm 4 L·mol ‑1 cm ‑1 ), the medium-intensity absorption occurs in the range of 300-320nm, the maximum excitation wavelength is 376nm, and the maximum emission wavelength is 609nm, showing high-efficiency orange luminescence; the luminescence quantum efficiency (PLQYs) of its solid powder at 293K is 45%. The lifetime is 2.26μs, and it is an excellent OLED photoluminescent material.

Description

Technical field

[0001] The present invention belongs to the art of organic complex synthesis, and more particularly to a benzimidazole bisphosphine Cu (I) complex and its preparation method thereof. Background technique

[0002] With the continuous development of society and science and technology, luminous materials have become one of the most active topics in the field of materials. The luminescent material has a variety of types, and can be divided into photoluminescence, electroluminescent, bioluminescence, chemiluminescence, and the like by light-emitting energy sources. In various different illumination types, electroluminescent devices are constantly being studied. Organic Electrical Device (OLED) is a mainstream trend of energy-saving lighting and new display technologies, which has become the mainstream trend of energy-saving lighting and new display technology, and has been used in life, such as Today's latest mobile display terminal Huawei P40 series. Stable, efficient...

Examples

Embodiment 1

[0051](1) Add aniline (3.3 mL, 36.2 mmol), 2,6-diitropylbenzene (3 ml, 30 mmol) and no water supply (1.8 g, 30 mmol) to 9 ml dimethyl sulfoxide, stirring After dissolving, the reaction was 15 h at 95 ° C; after the reaction was completed, the system was cooled to room temperature, and then 30 ml of distilled water was added to the reaction system, stirred to a large amount of red precipitate, and precipitate filtered and washed 3 times with 30 ml (10 ml × 3 times). 3 times, Filtering the solid is dried in a dry box to obtain an intermediate product.

[0052] (2) The intermediates A (7 g, 20 mmol) obtained by step (1) and the intermediate dyldimeter (1.34 g, 10 mmol) were added to 120 ml of mixed solvent (the volume ratio of ethanol and water was 5: 1), stirred Dissolve, then adding sodium sulfite (20 g, 120 mmol), refluxed at 125 ° C for 8 h; after the reaction was completed, the system was cooled to room temperature, and the ethanol in the recovery system was completed, then the ...

Embodiment 2

[0056] (1) Add aniline (3.3 mL, 36.2 mmol), 2,6-diitropylbenzene (3 ml, 30 mmol) and no water supply (1.8 g, 30 mmol) to 9 ml dimethyl sulfoxide, stirring After dissolving, it was 100 ° C for 12 h; after the reaction was completed, the system was cooled to room temperature, and then 30 ml of distilled water was added to the reaction system, stirred to a large amount of red precipitation, filtered precipitate and washed 3 times with 30 mL (10 mL × 3 times). 3 times, Filtering the solid is dried in a dry box to obtain an intermediate product.

[0057] (2) The intermediates A (7 g, 20 mmol) obtained by step (1) and the intermediate dyldimeter (1.34 g, 10 mmol) were added to 120 ml of mixed solvent (the volume ratio of ethanol and water was 5: 1), stirred Dissolved, then adding sodium sulfite (20 g, 120 mmol), and refluxed at 130 ° C for 6 h; after the reaction was completed, the system was cooled to room temperature, and the ethanol in the recovery system was completed, then the orga...

Embodiment 3

[0061] (1) Add aniline (3.3 mL, 36.2 mmol), 2,6-diitropylbenzene (3 ml, 30 mmol) and no water supply (1.8 g, 30 mmol) to 9 ml dimethyl sulfoxide, stirring After the dissolution was complete, the system was reacted at 98 ° C for 14 h; after the reaction was completed, the system was cooled to room temperature, and then 30 ml of distilled water was added to the reaction system, stirred to a large amount of red precipitate, and precipitate and washed 3 times with 30 mL (10 mL × 3 times). 3 times, Filtering the solid is dried in a dry box to obtain an intermediate product.

[0062] (2) The intermediates A (7 g, 20 mmol) obtained by step (1) and the intermediate dyldimeter (1.34 g, 10 mmol) were added to 120 ml of mixed solvent (the volume ratio of ethanol and water was 5: 1), stirred Dissolve, then adding sodium sulfite (20 g, 120 mmol), refluxed at 128 ° C for 7 h; after the reaction was completed, the system was cooled to room temperature, and the ethanol in the recovery system was ...

Technical field

[0001] The present invention belongs to the art of organic complex synthesis, and more particularly to a benzimidazole bisphosphine Cu (I) complex and its preparation method thereof. Background technique

[0002] With the continuous development of society and science and technology, luminous materials have become one of the most active topics in the field of materials. The luminescent material has a variety of types, and can be divided into photoluminescence, electroluminescent, bioluminescence, chemiluminescence, and the like by light-emitting energy sources. In various different illumination types, electroluminescent devices are constantly being studied. Organic Electrical Device (OLED) is a mainstream trend of energy-saving lighting and new display technologies, which has become the mainstream trend of energy-saving lighting and new display technology, and has been used in life, such as Today's latest mobile display terminal Huawei P40 series. Stable, efficient...

Examples

Embodiment 1

[0051](1) Add aniline (3.3 mL, 36.2 mmol), 2,6-diitropylbenzene (3 ml, 30 mmol) and no water supply (1.8 g, 30 mmol) to 9 ml dimethyl sulfoxide, stirring After dissolving, the reaction was 15 h at 95 ° C; after the reaction was completed, the system was cooled to room temperature, and then 30 ml of distilled water was added to the reaction system, stirred to a large amount of red precipitate, and precipitate filtered and washed 3 times with 30 ml (10 ml × 3 times). 3 times, Filtering the solid is dried in a dry box to obtain an intermediate product.

[0052] (2) The intermediates A (7 g, 20 mmol) obtained by step (1) and the intermediate dyldimeter (1.34 g, 10 mmol) were added to 120 ml of mixed solvent (the volume ratio of ethanol and water was 5: 1), stirred Dissolve, then adding sodium sulfite (20 g, 120 mmol), refluxed at 125 ° C for 8 h; after the reaction was completed, the system was cooled to room temperature, and the ethanol in the recovery system was completed, then the ...

Embodiment 2

[0056] (1) Add aniline (3.3 mL, 36.2 mmol), 2,6-diitropylbenzene (3 ml, 30 mmol) and no water supply (1.8 g, 30 mmol) to 9 ml dimethyl sulfoxide, stirring After dissolving, it was 100 ° C for 12 h; after the reaction was completed, the system was cooled to room temperature, and then 30 ml of distilled water was added to the reaction system, stirred to a large amount of red precipitation, filtered precipitate and washed 3 times with 30 mL (10 mL × 3 times). 3 times, Filtering the solid is dried in a dry box to obtain an intermediate product.

[0057] (2) The intermediates A (7 g, 20 mmol) obtained by step (1) and the intermediate dyldimeter (1.34 g, 10 mmol) were added to 120 ml of mixed solvent (the volume ratio of ethanol and water was 5: 1), stirred Dissolved, then adding sodium sulfite (20 g, 120 mmol), and refluxed at 130 ° C for 6 h; after the reaction was completed, the system was cooled to room temperature, and the ethanol in the recovery system was completed, then the orga...

Embodiment 3

[0061] (1) Add aniline (3.3 mL, 36.2 mmol), 2,6-diitropylbenzene (3 ml, 30 mmol) and no water supply (1.8 g, 30 mmol) to 9 ml dimethyl sulfoxide, stirring After the dissolution was complete, the system was reacted at 98 ° C for 14 h; after the reaction was completed, the system was cooled to room temperature, and then 30 ml of distilled water was added to the reaction system, stirred to a large amount of red precipitate, and precipitate and washed 3 times with 30 mL (10 mL × 3 times). 3 times, Filtering the solid is dried in a dry box to obtain an intermediate product.

[0062] (2) The intermediates A (7 g, 20 mmol) obtained by step (1) and the intermediate dyldimeter (1.34 g, 10 mmol) were added to 120 ml of mixed solvent (the volume ratio of ethanol and water was 5: 1), stirred Dissolve, then adding sodium sulfite (20 g, 120 mmol), refluxed at 128 ° C for 7 h; after the reaction was completed, the system was cooled to room temperature, and the ethanol in the recovery system was ...

Images