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Trifluoreneamine compound, trifluoreneamine polymer luminescent material and preparation methods and application thereof

A compound, trifluorene amine technology, applied in the field of light-emitting conjugated polymer materials, can solve the problems affecting the device emission light saturation color purity, light-emitting color stability, high hole injection, obstacles, etc., to improve hole injection characteristics, improve The effect of stability, broad development and application prospects

Inactive Publication Date: 2014-04-02
SOUTH CHINA UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The most representative of the existing polymer blue light-emitting materials is polyfluorene, but because of the rigid planar structure of fluorene, the material is easy to form an excimer complex and emit long-wavelength light, which seriously affects the saturated color of the light emitted by the device. Purity and stability of emission color
At the same time, polyfluorene has a higher hole injection barrier due to its lower lowest occupied molecular orbital (HOMO) energy level.

Method used

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  • Trifluoreneamine compound, trifluoreneamine polymer luminescent material and preparation methods and application thereof
  • Trifluoreneamine compound, trifluoreneamine polymer luminescent material and preparation methods and application thereof
  • Trifluoreneamine compound, trifluoreneamine polymer luminescent material and preparation methods and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Step 1: Preparation of 2-nitrofluorene

[0052]

[0053] Dissolve fluorene (33.2g, 0.2mol) in 200ml of glacial acetic acid, stir, heat to about 60°C, use a constant pressure dropping funnel to drop concentrated HNO diluted with 15ml of glacial acetic acid 3 (32ml, 0.464mol). After the dropwise addition was completed, the reaction was carried out at 60° C. for 3 hours. The reaction mixture was poured into ice water, extracted with dichloromethane, the obtained organic layer was washed 3 times with saturated saline solution, and the organic phases were combined and dried over anhydrous magnesium sulfate. The filtrate after suction filtration was desolventized under reduced pressure, and then recrystallized with absolute ethanol to obtain 30.3 g of a khaki solid. Yield 71.6%.

[0054] 1 H NMR (300MHz, CDCl 3 ), δ(ppm): 8.71(s, 1H), 8.60-8.31(m, 1H), 7.91-7.88(m, 2H), 7.66-7.64(m, 1H), 7.48-7.46(m, 2H), 4.03(s, 2H).

[0055] Step 2: Preparation of 2-nitro-9,9-dioc...

Embodiment 2

[0090] The first seven steps of the present embodiment are the same as the first seven steps of Embodiment 1.

[0091] Step 8: Preparation of 2-cyano-7-nitro-9,9-dioctylfluorene

[0092]

[0093] Under an argon atmosphere, 2-nitro-7-bromo-9,9-dioctylfluorene (2.05g, 4mmol), CuCN (0.389g, 4mmol), DMF (30ml) were added to a 250ml three-necked flask, After stirring evenly, gradually raise the temperature to about 150°C, and react under reflux for about 15 hours, showing a light yellow color. Overnight, it was found to be orange-red. It was extracted with dichloromethane, washed three times with saturated brine, and the obtained organic layer was dried over anhydrous magnesium sulfate. After suction filtration, the resulting filtrate was freed of solvent under reduced pressure. For column separation, the mobile phase used is dichloromethane / petroleum ether=1:6, remove the raw material point, dichloromethane / petroleum ether=1:3, collect the second point. Vacuum drying afford...

Embodiment 3

[0110] The first seven steps of the present embodiment are the same as the first seven steps of Embodiment 1.

[0111] Step 8: Preparation of 2-carbazole-7-nitro-9,9-dioctylfluorene

[0112]

[0113]3,5-2-nitro-7-bromo-9,9-dioctylfluorene (1.03g, 2mmol), carbazole (0.334g, 2mmol) were added to a 50ml three-necked flask under an argon atmosphere. , potassium carbonate (0.849g, 6mmol), dimethylsulfoxide 30ml, copper powder (5g, 78mmol). After stirring evenly, the temperature was raised to 150° C. for 12 hours of reaction. After cooling, it was extracted with dichloromethane, washed three times with saturated brine, and the obtained organic layer was dried over anhydrous magnesium sulfate. After suction filtration, the resulting filtrate was freed of solvent under reduced pressure. For column separation, the mobile phase used is dichloromethane / petroleum ether=1:8, remove the raw material point, dichloromethane / petroleum ether=1:4, collect the second point. Obtained 0.320 ...

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Abstract

The invention discloses a trifluoreneamine compound, a trifluoreneamine polymer luminescent material and preparation methods and application thereof. The material takes trifluoreneamine as a framework; the bipolarity and the illuminant color of the luminescent material can be regulated and controlled by changing the chemical structure of a side chain of the trifluoreneamine polymer luminescent material; and the chemical structure of the material is shown in the specifications. The preparation method comprises the following steps of: performing a series of simple reactions on fluorene serving as an initial reaction raw material; and performing a Suzuki coupling reaction under the catalysis of palladium and performing double-boric acid ester alternative copolymerization on fluorene to obtain a target polymer, namely the luminescent material. The material is easy to synthesize, is convenient to purify, has higher solubility, film forming property, and film form stability and high photoluminescence and electrofluorescence efficiencies, and is applied to a polymer electroluminescent diode luminous layer.

Description

technical field [0001] The invention relates to a light-emitting conjugated polymer material, in particular to a polymer light-emitting material with trifluorenamine as a skeleton, a preparation method thereof, and an application of the material in a polymer light-emitting diode. Background technique [0002] Since Burroughes and Friend first reported polymer light-emitting diodes (PLEDs), in the past nearly two decades, PLEDs have aroused intense research and development interest in fabricating ultra-thin, full-color, and large-area flat-panel displays. made great progress. The solution processability of PLEDs allows people to prepare devices by low-cost printing techniques, such as inkjet printing and screen printing, which are lower in cost than vacuum-evaporated small-molecule organic light-emitting diodes. is also more feasible. In order to realize PLEDs-based flat-panel displays and solid-state lighting, high-performance red, green, and blue light-emitting polymers a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C211/61C07C255/58C07D209/86C07D271/107C07C209/10C07C253/30C09K11/06C08G61/12H01L51/54
Inventor 苏仕健叶华彭俊彪曹镛赵伟明
Owner SOUTH CHINA UNIV OF TECH
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