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Polyarylether light-emitting material with main chain containing naphthalimide and synthesis method thereof

A technology of naphthalimide and luminescent material, which is applied in the field of polyarylene ether luminescent material containing naphthalimide in the main chain and its synthesis, can solve the problem of low glass transition temperature of conjugated polymer, influence on device stability, The problems of increasing synthesis steps, etc., achieve the effects of excellent solubility, reliable thermal stability, and overcoming easy crystallization.

Inactive Publication Date: 2012-11-07
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the main problems in the synthesis of conjugated polymers have been gradually solved, the number of synthetic steps is also increasing, making the process more cumbersome and purification more difficult
At the same time, the glass transition temperature of most unmodified or modified conjugated polymers is not high, which affects the stability of the device

Method used

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  • Polyarylether light-emitting material with main chain containing naphthalimide and synthesis method thereof
  • Polyarylether light-emitting material with main chain containing naphthalimide and synthesis method thereof
  • Polyarylether light-emitting material with main chain containing naphthalimide and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] (1) Synthesis of phenol sodium salt: Add 2.28 g of bisphenol A and 0.8 g of sodium hydroxide into a 50 mL single-necked bottle filled with 20 mL of methanol, pass through the nitrogen protection, react at room temperature for 3 h, and then raise the temperature to 60 ℃, remove the solvent methanol under reduced pressure; put the bottles together in a vacuum drying oven at 80 ℃ to dry to remove water, rinse the resulting solid with a small amount of methanol to remove residual reactants, and dry to obtain the product sodium phenolate.

[0026] (2) Synthesis of bishalogenated naphthalimide monomer: Add 3.048 g of 4-bromo-1,8-naphthalene dicarboxylic anhydride (recrystallized from chlorobenzene), 1.72 g of p-bromoaniline into a 50 mL three-necked flask, 20 mL of dimethylacetamide (DMAc), 5 mL of toluene, 0.5 mL of pyridine, and nitrogen protection at the same time. Stir at room temperature for 2 h, then raise the temperature to 140°C for 6 h with toluene and water, and the...

Embodiment 2

[0032] (1) Synthesis of phenol sodium salt: Add 2.28 g of bisphenol A and 0.8 g of sodium hydroxide into a 50 mL single-necked bottle filled with 20 mL of methanol, pass through the nitrogen protection, react at room temperature for 3 h, and then raise the temperature to 60 ℃, remove the solvent methanol under reduced pressure; put the bottles together in a vacuum drying oven at 80 ℃ to dry to remove water, rinse the resulting solid with a small amount of methanol to remove residual reactants, and dry to obtain the product sodium phenolate.

[0033](2) Synthesis of bishalogenated naphthalimide monomer: Add 2.909 g of 4-bromo-1,8-naphthalene dicarboxylic anhydride (recrystallized from chlorobenzene), 1.72 g of p-bromoaniline into a 50 mL three-necked flask, 20 mL of dimethylacetamide (DMAc), 5 mL of toluene, 0.5 mL of pyridine, and nitrogen protection at the same time. Stir at room temperature for 2 h, then raise the temperature to 140°C for 6 h with toluene and water, and then...

Embodiment 3

[0039] (1) Synthesis of phenol sodium salt: Add 2.28 g of bisphenol A and 0.8 g of sodium hydroxide into a 50 mL single-necked bottle filled with 20 mL of methanol, pass through the nitrogen protection, react at room temperature for 3 h, and then raise the temperature to 60 ℃, remove the solvent methanol under reduced pressure; put the bottles together in a vacuum drying oven at 80 ℃ to dry to remove water, rinse the resulting solid with a small amount of methanol to remove residual reactants, and dry to obtain the product sodium phenolate.

[0040] (2) Synthesis of bishalogenated naphthalimide monomer: Add 3.047 g of 4-bromo-1,8-naphthalene dicarboxylic anhydride (recrystallized from chlorobenzene), 1.72 g of p-bromoaniline into a 50 mL three-necked flask, 20 mL of dimethylacetamide (DMAc), 5 mL of toluene, 0.5 mL of pyridine, and nitrogen protection at the same time. Stir at room temperature for 2 h, then raise the temperature to 140°C for 6 h with toluene and water, and the...

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Abstract

The invention belongs to the technical field of light-emitting materials of photoelectric display devices and particularly relates to a synthesis method of a polyarylether light-emitting material with a main chain containing naphthalimide. The important contents of the synthesis method are as follows: halogenated naphthalic acid anhydride and halogenated aromatic amine are used to synthesize halogenated naphthalimide monomer, and then the halogenated naphthalimide monomer and the prepared bisphenol sodium salt are subjected to nucleophilic substitution reaction to obtain the polyarylether light-emitting material with the main chain containing a naphthalimide structure. Compared with the prior art, the invention has the following advantages that the advantages of small molecules and polymers are combined; and in the preparation process of the material, the cost of raw materials is low, a metal catalyst is not needed, the process is short and the product is easy for purification. The polyarylether light-emitting material prepared by the invention has good stability and good light-emitting performance, can be dissolved in different solvents, is conveniently coated into a film, and isapplicable to manufacture of organic light-emitting devices.

Description

technical field [0001] The invention relates to a polyarylether luminescent material and a synthesis method thereof, in particular to a polyarylether luminescent material whose main chain contains naphthalimide and a synthesis method thereof. Background technique [0002] As a luminescent material, polymers have incomparable advantages over inorganic materials and organic small molecule materials: good environmental stability, easy device preparation, easier adjustment of its energy band structure, and easy realization of multicolor luminescence. Therefore, the upsurge of research on the synthesis of polyphenylene vinylene, polyfluorene, polythiophene and other conjugated polymer luminescent materials and the adjustment of luminous color is increasing day by day. However, it is found in the research that the synthesis and purification of conjugated polymers are quite difficult. Catalysts or oxidants containing metal ions are used in the process of synthesizing conjugated po...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G65/40C09K11/06
Inventor 贺英陈杰朱棣潘照东张瑶斐王均安
Owner SHANGHAI UNIV
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