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A kind of adamantane modified polycarbazole polymer luminescent material and preparation method thereof

A technology of azole polymer and light-emitting material, which is applied in the field of adamantane-modified polycarbazole polymer light-emitting material and its preparation, can solve the problems of limiting the application range of carbazole material, poor device stability, unstable light emission, etc. Possibility of fluorescence quenching, convenient film formation, and excellent solubility

Inactive Publication Date: 2018-01-23
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the glass transition temperature Tg of most polycarbazole-based light-emitting materials is low, which makes the stability of the device poor, resulting in unstable light emission and short device life, which limits the application range of carbazole materials.

Method used

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  • A kind of adamantane modified polycarbazole polymer luminescent material and preparation method thereof
  • A kind of adamantane modified polycarbazole polymer luminescent material and preparation method thereof
  • A kind of adamantane modified polycarbazole polymer luminescent material and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] (1) Preparation of 4,4'-dibromo-2-nitrobiphenyl

[0056] 4,4'-Dibromobiphenyl (2g, 6.41mmol) and glacial acetic acid (30ml) were added into the reaction flask, stirred by magnetic force, and the temperature of the oil bath was raised to 100°C. Through a constant-pressure dropping funnel, dropwise add a mixed solution of distilled water (0.75mL) and fuming nitric acid (9.25mL), continue stirring at 100°C for 0.5h, then pour into 500mL of ice water, stir, suction filter, and vacuum-dry the solid. The solid was recrystallized from ethanol to obtain 4,4'-dibromo-2-nitrobiphenyl as a light yellow solid with a yield of 68.2%;

[0057] (2) Preparation of 2,7-dibromocarbazole

[0058] Add 4,4'-dibromo-2-nitrobiphenyl (2g, 5.60mmol) and triphenylphosphine (4.40g, 16.80mmol) of step (1) into a 250mL three-necked round-bottomed flask, and add the reaction solvent o-dichlorobenzene 125mL, stirred vigorously, and raised the temperature to 170°C to reflux, reacted for 9h, cooled, a...

Embodiment 2

[0072] (1) Preparation of 4,4'-dibromo-2-nitrobiphenyl

[0073] 4,4'-Dibromobiphenyl (2g, 6.41mmol) and glacial acetic acid (30ml) were added into the reaction flask, stirred by magnetic force, and the temperature of the oil bath was raised to 100°C. A mixed solution of distilled water (0.62 mL) and fuming nitric acid (9.25 mL) was added dropwise through a constant pressure dropping funnel. After continuing stirring at 100° C. for 0.5 h, pour into 500 mL of ice water, stir, filter with suction, and dry the solid in vacuo. The crude product was recrystallized from ethanol to obtain 4,4'-dibromo-2-nitrobiphenyl as a light yellow solid with a yield of 60.2%.

[0074] (2) Preparation of 2,7-dibromocarbazole

[0075] 4,4'-Dibromo-2-nitrobiphenyl (2g, 5.60mmol) and triphenylphosphine (4.00g, 15.30mmol) were added into a 250mL three-neck round bottom flask. 125 mL of the reaction solvent o-dichlorobenzene was added, stirred vigorously, and heated to 170° C. to reflux. After react...

Embodiment 3

[0088] (1) Preparation of 4,4'-dibromo-2-nitrobiphenyl

[0089] 4,4'-Dibromobiphenyl (2g, 6.41mmol) and glacial acetic acid (30ml) were added into the reaction flask, stirred by magnetic force, and the temperature of the oil bath was raised to 100°C. A mixed solution of distilled water (0.93 mL) and fuming nitric acid (9.25 mL) was added dropwise through a constant pressure dropping funnel. After continuing stirring at 100° C. for 0.5 h, pour into 500 mL of ice water, stir, filter with suction, and dry the solid in vacuo. The crude product was recrystallized from ethanol to obtain 4,4'-dibromo-2-nitrobiphenyl as a light yellow solid with a yield of 62.8%.

[0090] (2) Preparation of 2,7-dibromocarbazole

[0091] 4,4'-Dibromo-2-nitrobiphenyl (2g, 5.60mmol) and triphenylphosphine (6.00g, 22.91mmol) were added into a 250mL three-neck round bottom flask. 125 mL of the reaction solvent o-dichlorobenzene was added, stirred vigorously, and heated to 170° C. to reflux. After react...

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Abstract

The invention discloses an adamantine modified poly-carbazole high-polymer luminescent material and a preparation method thereof, and belongs to the technical field of polymer synthesis and functional polymer preparation. The high-polymer luminescent material is narrow in molecular weight distribution, the decomposition temperature is about 420 DEG C, and the fluorescent quantum efficiency of a solution can reach 0.85. Due to existence of adamantine groups, the copolymer has good thermal stability, meanwhile, the luminescence property of the material is further improved, and the optimized molar ratio of adamantine monomers to carbazole monomers is obtained. A Suzuki reaction polymerization method is adopted, and the material is simple and effective, has universality, and can be popularized to preparation of other adamantine containing polymer materials. The polymer is suitable for the organic electronic fields of light-emitting diodes, colored flat-panel displayers, organic lasers and the like.

Description

technical field [0001] The invention belongs to the technical fields of polymer synthesis and functional polymer preparation, and in particular relates to an adamantane-modified polycarbazole polymer luminescent material and a preparation method thereof. Background technique [0002] In 1987, Tang et al. from Eastern Kodak Company in the United States and Friend et al. from the University of Cambridge in the United Kingdom reported organic electroluminescent devices with a sandwich structure made of organic and polymer fluorescent materials and polymer luminescence of polyphenylene vinylene (PPV) in 1990. Diodes have opened up a new field of polymer flat panel display. Compared with inorganic materials, organic polymer materials have the advantages of low material preparation cost, simple process, good film-forming properties and flexibility. Therefore, the development of new organic optoelectronic materials with marketable potential has attracted the attention and investme...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12C09K11/06
CPCC08G61/124C08G2261/18C08G2261/3241C08G2261/3325C08G2261/522C08G2261/592C09K11/06
Inventor 郭建维罗涛柳滢春朱东雨杨楚芬崔亦华
Owner GUANGDONG UNIV OF TECH
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