Pure organic phosphorescent material with afterglow luminescence performance and ultra-long service life, method for preparing pure organic phosphorescent material and application thereof

Abstract

The invention discloses an ultra-long-life pure organic phosphorescent material with afterglow luminescence performance and its preparation method and application. The pure organic phosphorescent material is composed of phenylphosphorus and carbazole structure, which is DNCzPS or DNCzPSe. The carbazole React with phenylphosphorous dichloride at low temperature to obtain the intermediate dicarbazolylphenylphosphorus; then the intermediate can be subjected to sulfidation or selenization reaction to obtain the corresponding products DNCzPS and DNCzPSe. This type of pure organic phosphorescent material has obvious afterglow luminescence properties, which greatly prolongs the luminescence lifetime of organic materials. The prepared RMB anti-counterfeiting and multi-level two-dimensional code anti-prototype device has the characteristics of high resolution and multi-level anti-counterfeiting.

Description

technical field

[0001] The invention belongs to the technical field of organic afterglow luminescent materials, and in particular relates to an ultra-long-life pure organic phosphorescent material with afterglow luminescence performance and a preparation method and application thereof. Background technique

[0002] Since the 1970s, high-tech represented by new materials, new energy, information, nanotechnology, etc. has become the subject of global research. As the most important part of strategic emerging industries, new materials are the keel of the country's seven strategic emerging industries. Organic optoelectronic functional materials have received extensive research and attention due to their excellent luminescent properties, chemical and physical stability. In recent years, with the development of optoelectronic devices, organic optoelectronic functional materials with long-lived excited state properties have been favored in the fields of bioimaging and solar cells,...

Examples

preparation example Construction

[0029] The synthesis method of the above-mentioned ultra-long-life pure organic phosphorescent material comprises the following steps:

[0030] ①React carbazole with phenylphosphorous dichloride at low temperature to obtain the intermediate dicarbazolylphenylphosphorus;

[0031] ② After sulfuration or selenization of the intermediates, the corresponding products DNCzPS and DNCzPSe (X are S and Se, respectively) can be obtained.

[0032] The final product obtained by the above method is a crystal.

[0033] The above-mentioned ultra-long-life pure organic phosphorescent materials are used in the preparation of products such as data encryption and anti-counterfeiting labels.

Embodiment 1D

[0034] The synthesis of embodiment 1DNCzPS

[0035] The structural formula of DNCzPS is as follows:

[0036]

[0037] Put carbazole (1.00 g, 5.99 mmol) into a 50 mL single-necked bottle, add a stirring bar, vacuumize and blow nitrogen, repeat 3 times. Use a syringe to slowly add 20 mL of freshly steamed anhydrous THF to dissolve carbazole. After the carbazole is completely dissolved, place the round bottom flask in an ice bath at 0°C and cool for 15 min. Add n-butyllithium (4.5mL, 1.6M) slowly to the carbazole solution dropwise at a rate of 1mL / 2min, resulting in a bright yellow solution. React at 0°C for about 1-2h. Add phenylphosphine dichloride (0.41mL, 2.99mmol) dropwise to the lithium reagent of carbazole, then slowly raise the temperature to room temperature 25°C at a rate of 2-3°C / min, and react at a low temperature of 0°C for 10-12 hours . After the reaction, pour the reaction liquid into water to quench the reaction, then extract three times with dichloromethan...

Embodiment 2D

[0039] The synthesis of embodiment 2DNCzPSe

[0040] The structural formula of DNCzPSe is as follows:

[0041]

[0042] Put carbazole (1.00 g, 5.99 mmol) into a 50 mL single-necked bottle, add a stirring bar, vacuumize and blow nitrogen, repeat 3 times. Use a syringe to slowly add 20 mL of freshly steamed anhydrous THF to dissolve carbazole. After the carbazole is completely dissolved, place the round bottom flask in an ice bath at 0°C and cool for 15 min. Add n-butyllithium (4.5mL, 1.6M) slowly to the carbazole solution dropwise at a rate of 1mL / 2min, resulting in a bright yellow solution. React at 0°C for about 1-2h. Add phenylphosphine dichloride (0.41mL, 2.99mmol) dropwise to the lithium reagent of carbazole, then slowly raise the temperature to room temperature 25°C at a rate of 2-3°C / min, and react at a low temperature of 0°C for 10-12 hours . After the reaction, pour the reaction liquid into water to quench the reaction, then extract three times with dichlorometh...

technical field

[0001] The invention belongs to the technical field of organic afterglow luminescent materials, and in particular relates to an ultra-long-life pure organic phosphorescent material with afterglow luminescence performance and a preparation method and application thereof. Background technique

[0002] Since the 1970s, high-tech represented by new materials, new energy, information, nanotechnology, etc. has become the subject of global research. As the most important part of strategic emerging industries, new materials are the keel of the country's seven strategic emerging industries. Organic optoelectronic functional materials have received extensive research and attention due to their excellent luminescent properties, chemical and physical stability. In recent years, with the development of optoelectronic devices, organic optoelectronic functional materials with long-lived excited state properties have been favored in the fields of bioimaging and solar cells,...

Examples

preparation example Construction

[0029] The synthesis method of the above-mentioned ultra-long-life pure organic phosphorescent material comprises the following steps:

[0030] ①React carbazole with phenylphosphorous dichloride at low temperature to obtain the intermediate dicarbazolylphenylphosphorus;

[0031] ② After sulfuration or selenization of the intermediates, the corresponding products DNCzPS and DNCzPSe (X are S and Se, respectively) can be obtained.

[0032] The final product obtained by the above method is a crystal.

[0033] The above-mentioned ultra-long-life pure organic phosphorescent materials are used in the preparation of products such as data encryption and anti-counterfeiting labels.

Embodiment 1D

[0034] The synthesis of embodiment 1DNCzPS

[0035] The structural formula of DNCzPS is as follows:

[0036]

[0037] Put carbazole (1.00 g, 5.99 mmol) into a 50 mL single-necked bottle, add a stirring bar, vacuumize and blow nitrogen, repeat 3 times. Use a syringe to slowly add 20 mL of freshly steamed anhydrous THF to dissolve carbazole. After the carbazole is completely dissolved, place the round bottom flask in an ice bath at 0°C and cool for 15 min. Add n-butyllithium (4.5mL, 1.6M) slowly to the carbazole solution dropwise at a rate of 1mL / 2min, resulting in a bright yellow solution. React at 0°C for about 1-2h. Add phenylphosphine dichloride (0.41mL, 2.99mmol) dropwise to the lithium reagent of carbazole, then slowly raise the temperature to room temperature 25°C at a rate of 2-3°C / min, and react at a low temperature of 0°C for 10-12 hours . After the reaction, pour the reaction liquid into water to quench the reaction, then extract three times with dichloromethan...

Embodiment 2D

[0039] The synthesis of embodiment 2DNCzPSe

[0040] The structural formula of DNCzPSe is as follows:

[0041]

[0042] Put carbazole (1.00 g, 5.99 mmol) into a 50 mL single-necked bottle, add a stirring bar, vacuumize and blow nitrogen, repeat 3 times. Use a syringe to slowly add 20 mL of freshly steamed anhydrous THF to dissolve carbazole. After the carbazole is completely dissolved, place the round bottom flask in an ice bath at 0°C and cool for 15 min. Add n-butyllithium (4.5mL, 1.6M) slowly to the carbazole solution dropwise at a rate of 1mL / 2min, resulting in a bright yellow solution. React at 0°C for about 1-2h. Add phenylphosphine dichloride (0.41mL, 2.99mmol) dropwise to the lithium reagent of carbazole, then slowly raise the temperature to room temperature 25°C at a rate of 2-3°C / min, and react at a low temperature of 0°C for 10-12 hours . After the reaction, pour the reaction liquid into water to quench the reaction, then extract three times with dichlorometh...

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