Polyimide with aggregation-induced emission property and preparation method of polyimide

Abstract

The invention discloses a polyimide with aggregation-induced emission property and a preparation method of the polyimide. During synthesis, a diamine monomer containing a tetraphenyl ethylene radicalgroup, a dianhydride monomer containing a tetraphenyl ethylene radical group, a normal dianhydride monomer and a normal diamine monomer are used for preparation through more than two components of solution polycondensation methods, and polycondensation components at least comprise one of the diamine monomer containing the tetraphenyl ethylene radical group or the dianhydride monomer containing thetetraphenyl ethylene radical group. A synthetic method of the polyimide is simple, the preparation cost is low, solubleness of the obtained polyimide is good, processing is easy, good heat stabilityis achieved, the obvious aggregation-induced emission property is achieved, wide application prospects in the fields of oganic light emitting diodes, a luminescent layer of a electroluminescence device, and a high-ranking information anti-fake material are provided.

Description

technical field

[0001] The invention relates to the preparation of organic light-emitting materials, in particular to a polyimide with aggregation-induced light-emitting properties and a preparation method thereof. Background technique

[0002] With the advancement of display technology, organic light-emitting diodes (organic light-emitting diodes, OLEDs) are known for their active light emission, full-color display, low power consumption, low start-up voltage, high brightness, fast response, wide viewing angle, simple processing technology and low cost. It has become one of the research hotspots in the field of organic optoelectronics in recent years. Compared with organic small molecule luminescent materials, polymer luminescent materials can be formed into large-area films by various low-cost technologies such as spin coating, inkjet printing, and dipping, and made into flexible devices with simple structures, and light-emitting polymers generally have large conjugated T...

Examples

Embodiment 1

[0031] (1) Preparation of polyamic acid

[0032] Under the protection of nitrogen, add diamine monomer (1.366g, 0.0025mol) containing tetraphenylethylene group and 25mL of N-methylpyrrolidone into a 50mL three-necked flask with a stirring device, and stir to make the tetraphenylethylene group After the group of diaminated monomers was completely dissolved, pyromellitic dianhydride (0.5453 g, 0.0025 mol) was added to the solution in batches, and the polyamic acid solution was obtained after stirring and reacting at a constant temperature at 0° C. for 5 h.

[0033] (2) Preparation of polyimide

[0034] Add 3.7 mL of a mixed solution of acetic anhydride and triethylamine with a mass ratio of 1:1 to the polyamic acid solution obtained in step 1, stir at a constant temperature at 25°C for 12 hours, then stop the reaction, pour the reaction solution into water for precipitation, pump The solid product was collected by filtration and dried to obtain a polyimide solid.

Embodiment 2

[0036] (1) Preparation of polyamic acid

[0037] With embodiment 1.

[0038] (2) Preparation of polyimide

[0039] Put the polyamic acid solution obtained in step (1) on a clean glass plate, spin-coat it to form a film, and dry it at 70°C to remove the organic solvent. Each isothermally treated at 300°C for 2h to make it completely imidized. After the temperature of the glass plate is cooled to room temperature, the glass plate covered with the polyimide film is put into deionized water, and then the film and the glass plate are separated to obtain the polyimide film.

Embodiment 3

[0041] (1) Preparation of polyamic acid

[0042] Under the protection of nitrogen, add p-phenylenediamine monomer (0.2705, 0.0025mol) and 23mL of N-methylpyrrolidone into a 50mL three-necked flask with a stirring device, stir to completely dissolve the p-phenylenediamine monomer and pour into the solution A dianhydride monomer (1.64 g, 0.0025 mol) containing a tetraphenylethylene group was added in batches, and stirred at 5°C for 5 hours to obtain a polyamic acid solution.

[0043] (2) Preparation of polyimide

[0044] Add 3.7 mL of a mixed solution of acetic anhydride and triethylamine at a mass ratio of 1:1 to the polyamic acid solution obtained in step 1, and stir at 25°C for 12 hours to stop the reaction. The reaction solution was poured into water for precipitation, suction filtered, and the solid product was collected, and the polyimide solid was obtained after drying.

technical field

[0001] The invention relates to the preparation of organic light-emitting materials, in particular to a polyimide with aggregation-induced light-emitting properties and a preparation method thereof. Background technique

[0002] With the advancement of display technology, organic light-emitting diodes (organic light-emitting diodes, OLEDs) are known for their active light emission, full-color display, low power consumption, low start-up voltage, high brightness, fast response, wide viewing angle, simple processing technology and low cost. It has become one of the research hotspots in the field of organic optoelectronics in recent years. Compared with organic small molecule luminescent materials, polymer luminescent materials can be formed into large-area films by various low-cost technologies such as spin coating, inkjet printing, and dipping, and made into flexible devices with simple structures, and light-emitting polymers generally have large conjugated T...

Examples

Embodiment 1

[0031] (1) Preparation of polyamic acid

[0032] Under the protection of nitrogen, add diamine monomer (1.366g, 0.0025mol) containing tetraphenylethylene group and 25mL of N-methylpyrrolidone into a 50mL three-necked flask with a stirring device, and stir to make the tetraphenylethylene group After the group of diaminated monomers was completely dissolved, pyromellitic dianhydride (0.5453 g, 0.0025 mol) was added to the solution in batches, and the polyamic acid solution was obtained after stirring and reacting at a constant temperature at 0° C. for 5 h.

[0033] (2) Preparation of polyimide

[0034] Add 3.7 mL of a mixed solution of acetic anhydride and triethylamine with a mass ratio of 1:1 to the polyamic acid solution obtained in step 1, stir at a constant temperature at 25°C for 12 hours, then stop the reaction, pour the reaction solution into water for precipitation, pump The solid product was collected by filtration and dried to obtain a polyimide solid.

Embodiment 2

[0036] (1) Preparation of polyamic acid

[0037] With embodiment 1.

[0038] (2) Preparation of polyimide

[0039] Put the polyamic acid solution obtained in step (1) on a clean glass plate, spin-coat it to form a film, and dry it at 70°C to remove the organic solvent. Each isothermally treated at 300°C for 2h to make it completely imidized. After the temperature of the glass plate is cooled to room temperature, the glass plate covered with the polyimide film is put into deionized water, and then the film and the glass plate are separated to obtain the polyimide film.

Embodiment 3

[0041] (1) Preparation of polyamic acid

[0042] Under the protection of nitrogen, add p-phenylenediamine monomer (0.2705, 0.0025mol) and 23mL of N-methylpyrrolidone into a 50mL three-necked flask with a stirring device, stir to completely dissolve the p-phenylenediamine monomer and pour into the solution A dianhydride monomer (1.64 g, 0.0025 mol) containing a tetraphenylethylene group was added in batches, and stirred at 5°C for 5 hours to obtain a polyamic acid solution.

[0043] (2) Preparation of polyimide

[0044] Add 3.7 mL of a mixed solution of acetic anhydride and triethylamine at a mass ratio of 1:1 to the polyamic acid solution obtained in step 1, and stir at 25°C for 12 hours to stop the reaction. The reaction solution was poured into water for precipitation, suction filtered, and the solid product was collected, and the polyimide solid was obtained after drying.

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