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Arborization functional group side chain-containing polyfluorene macromolecule blue photoelectric material and application thereof

A functional group, polyalkyl fluorene technology, applied in the field of polyalkyl fluorene polymer blue optoelectronic materials, can solve the problems of red shift of emission wavelength, affecting the purity of emission color, etc., to reduce the chance of oxidation and improve holes Injection and transmission performance, effect of suppressing long-wave emission

Inactive Publication Date: 2009-11-11
NANCHANG HANGKONG UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, polyalkylfluorene derivatives are easily oxidized to form fluorenone at the 9-position of the fluorene ring, and the main chain of this type of polymer is easy to aggregate to form an exciplex, which leads to a red shift of the emission wavelength and affects the emission color. purity

Method used

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  • Arborization functional group side chain-containing polyfluorene macromolecule blue photoelectric material and application thereof
  • Arborization functional group side chain-containing polyfluorene macromolecule blue photoelectric material and application thereof
  • Arborization functional group side chain-containing polyfluorene macromolecule blue photoelectric material and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Synthesis of Intermediate 1

[0032] In a 100 ml three-necked flask, add 5.16 g (15.6 mmol) 9-(6-bromohexyl) carbazole, 1.00 g (7.1 mmol) 3,5-dihydroxybenzyl alcohol, 3.68 g (65 mmol) Anhydrous potassium carbonate, 0.38 g (1.42 mmol) of 18 crown 6 and 60 ml of anhydrous acetone form a mixed solution. The reaction mixture was stirred and refluxed under nitrogen atmosphere for 60 hours, and then cooled to room temperature naturally. The solvent was distilled off under reduced pressure, and the solid residue was extracted with a mixed solvent of dichloromethane and water. The organic phases were combined, dried over anhydrous magnesium sulfate, and filtered. The primary product was separated by column chromatography (dichloromethane as the eluent) to obtain a pure product with a yield of 85%. 1 HNMR (CDCl 3 , 300MHZ, δ / ppm): 8.21(d, 4H), 7.47-7.41(m, 8H), 7.35(s, 1H), 7.25-7.20(m, 4H), 6.51(s, 2H), 6.26(s , 1H), 4.66(s, 2H), 4.39(t, 4H), 3.88(t, 4H), 2.10-2.06(m, 8H), ...

Embodiment 2

[0034] Synthesis of Intermediate 2

[0035] In a 50 mL round bottom flask, add 2.79 g (4.38 mmol) of intermediate 1, 2.90 g (8.75 mmol) of carbon tetrabromide, 2.29 g (8.75 mmol) of triphenylphosphine and 25 mL of anhydrous dichloro methane. The reaction mixture was stirred at room temperature for 5 hours under an argon atmosphere, and then cooled to room temperature. The solvent was evaporated under reduced pressure. The solid residue was separated by column chromatography using dichloromethane as the eluent to obtain a light yellow pure product with a yield of 90%. 1 HNMR (CDCl 3 , 300MHZ, δ / ppm): 8.16(d, 4H), 7.49-7.41(m, 8H), 7.22-7.19(m, 4H), 6.47(s, 2H), 6.30(s, 1H), 4.38-4.21 (m, 6H), 3.86(t, 4H), 2.10-2.08(m, 8H), 1.84-1.82(m, 8H).

Embodiment 3

[0037] Synthesis of intermediate 3

[0038] In a 100 ml three-necked flask, add 0.154 g (0.48 mmol) of 2,7-dibromofluorene, 2.78 mg (0.01 mmol) of tetrabutylammonium chloride and 60 ml of dimethyl sulfoxide to form a mixed solution, and pass argon After deoxygenation for 10 minutes, 2 ml of 50% sodium hydroxide solution was added. A mixed solution containing 0.718 g (1 mmol) of intermediate 2 in 80 ml of dimethyl sulfoxide was added dropwise to the above solution with stirring. After the reaction mixture was stirred at reflux under nitrogen atmosphere for 8 hours at room temperature, water was added to quench the reaction. The mixture was extracted three times with dichloromethane, and the organic phases were combined, dried over anhydrous magnesium sulfate, and filtered. The primary product was separated by column chromatography (dichloromethane:petroleum ether=4:1 as eluent) to obtain a pure product with a yield of 80%. 1 HNMR (CDCl 3 , 400MHz, δ / ppm): 8.12(d, 8H), 7.53(...

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Abstract

The invention relates to a method for preparing an arborization functional group side chain-containing polyfluorene macromolecule blue photoelectric material. The material is prepared by the following steps: the Suzuki coupling polymerization reaction is applied, and under the catalysis action of organic palladium, arborization side chain-containing monomer and flourenyl hypoboric acid ester comonomer of which the inventory molar ratio is x: y: 1(x+y=1) are reacted for 48 to 100 hours at the temperature ranging from 60 to 150 DEG C in an organic solvent containing inorganic base. The method has the advantages that: the hole injection and the transmission performance of polyfluorene electroluminescent materials are improved, the shielding effect of the arborization side chain effectively avoids the defect that linear polyfluorene blue-light materials are easy to generate main chain aggregation to form exciplex, the chance of oxidation of main chain polyfluorene is reduced, and therefore the long wave emission of polyfluorene is effectively inhibited.

Description

technical field [0001] The invention relates to a polyalkylfluorene macromolecule blue photoelectric material containing dendritic functional group side chains and its application. Background technique [0002] With the development of information science and technology, the requirements for the performance of flat panel displays are getting higher and higher. Organic electroluminescent devices are known as the third-generation flat panel display technology due to their advantages such as low-voltage drive, self-luminescence, wide viewing angle, high efficiency, and rich colors. Organic electroluminescent materials are the key to realizing organic electroluminescent displays, and are generally divided into polymer materials and small molecule materials. Since the polymer electroluminescent diode was first reported by the Cavendish Laboratory of the University of Cambridge in 1990, it has developed very rapidly and is close to practical use. The efficiency and lifetime of po...

Claims

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Application Information

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IPC IPC(8): C09K11/06C08G61/02H01L51/56H01L51/52H01L51/54H01L27/32
Inventor 彭强
Owner NANCHANG HANGKONG UNIVERSITY
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