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Photoelectric functional material based on silazine unit and its preparation method and application

A photoelectric functional material, silazine technology, applied in luminescent materials, chemical instruments and methods, compounds of group 4/14 elements of the periodic table, etc., can solve problems such as limiting commercial applications, and achieve improved stability and electron transport The effect of performance, low cost, and simple preparation method

Active Publication Date: 2018-11-27
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

According to spin quantum statistics, under electro-excitation conditions, the ratio of singlet excitons to triplet excitons is about 1:3, while traditional electroluminescent devices can only use singlet excitons to emit light, and the internal quantum efficiency The limit is 25%, which greatly limits its commercial application

Method used

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  • Photoelectric functional material based on silazine unit and its preparation method and application
  • Photoelectric functional material based on silazine unit and its preparation method and application
  • Photoelectric functional material based on silazine unit and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Synthesis of Photoelectric Functional Material 1

[0024]

[0025] Step 1, add 10g of carbazole, 7.97g of cuprous iodide and 16.53g of potassium carbonate to the reaction bottle, vacuumize and blow nitrogen for three times, add 80mL of xylene under the protection of nitrogen, and measure 11.52mL of o-bromoiodobenzene with a syringe Add it into the reaction flask, and raise the temperature to 140° C. for 48 hours under the protection of nitrogen. The reaction solution was added with 150 mL of water, extracted with 3×150 mL of dichloromethane, and the organic phase was collected and dried over anhydrous sodium sulfate. The dichloromethane solution was spun out with a rotary evaporator. Then the crude product was dissolved in 50 mL of dichloromethane, added with silica gel powder, and the solvent was spin-dried, and purified by chromatography to obtain a bromine-containing intermediate.

[0026] Step 2, add 2g of bromine-containing intermediate to the reaction flask, ...

Embodiment 2

[0030] Synthesis of Photoelectric Functional Materials 2

[0031]

[0032] Step 1, add 10g of carbazole, 7.97g of cuprous iodide and 16.53g of potassium carbonate to the reaction bottle, vacuumize and blow nitrogen for three times, add 80mL of xylene under the protection of nitrogen, and measure 11.52mL of o-bromoiodobenzene with a syringe Add it into the reaction flask, and raise the temperature to 140° C. for 48 hours under the protection of nitrogen. The reaction solution was added with 150 mL of water, extracted with 3×150 mL of dichloromethane, and the organic phase was collected and dried over anhydrous sodium sulfate. The dichloromethane solution was spun out with a rotary evaporator. Then the crude product was dissolved in 50 mL of dichloromethane, added with silica gel powder, and the solvent was spin-dried, and purified by chromatography to obtain a bromine-containing intermediate.

[0033] Step 2, add 2g of bromine-containing intermediate to the reaction flask,...

Embodiment 3

[0037] Synthesis of Photoelectric Functional Materials 3

[0038]

[0039] Step 1, add 27.06g of carbazole, 20g of 1,4-dibromo-2,5-difluorobenzene and 61g of potassium carbonate to the reaction flask, vacuumize and blow nitrogen for three times, add 300mL of dimethyl sulfoxide under nitrogen protection, nitrogen Under protection, the temperature was raised to 150°C for 48 hours. Add 2000mL of water to the reaction solution, take the solid after suction filtration, and rinse with acetone to remove the raw material to obtain a bromine-containing intermediate.

[0040] Step 2, add 5g of bromine-containing intermediate to the reaction bottle, vacuumize, blow nitrogen repeatedly three times, add 150mL of anhydrous tetrahydrofuran (THF) under nitrogen protection, and then put the device into a dry ice / acetone bath at -78°C to cool 15min. Measure 10.6 mL of n-butyllithium n-hexane solution with a syringe, add it dropwise into the reaction flask, and react at -78°C for 1 h under ...

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Abstract

The invention provides a photoelectric functional material based on a silazine unit and its preparation method and application. The structural formula of the photoelectric functional material is shown in formula I or formula II: wherein R1 is phenyl, and R2 is methyl or phenyl. Its preparation method is to react carbazole with o-bromoiodobenzene or 1,4-dibromo-2,5-difluorobenzene, then react the bromine-containing intermediate with n-butyllithium, and then add diphenylchlorosilane or Methylphenylchlorosilane, and finally reacting silicon hydrogen derivatives with tert-butyl hydroperoxide to obtain photoelectric functional materials based on silazine units. The photoelectric functional material of the invention has high triplet state energy level, good hole transport performance and certain electron transport property, and the synthesis raw material is cheap. The organic electrophosphorescent device prepared by using the material of the invention has lower turn-on voltage, higher efficiency and stable luminous performance.

Description

technical field [0001] The invention belongs to the technical field of electroluminescent materials, and in particular relates to a photoelectric functional material based on silazine units and its preparation method and application. Background technique [0002] Organic light-emitting diodes (Organic light-emitting diodes, OLEDs) are a new generation of display and lighting technology. Compared with the widely used inorganic light-emitting diodes (LEDs), OLEDs have the advantages of light and thin devices, high brightness, low cost, and wide viewing angles, and have attracted extensive attention from scientific researchers in recent years. According to spin quantum statistics, under electro-excitation conditions, the ratio of singlet excitons to triplet excitons is about 1:3, while traditional electroluminescent devices can only use singlet excitons to emit light, and the internal quantum efficiency The limit is 25%, which greatly limits its commercial application. Electr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/10C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07F7/0816C07F7/0827C09K2211/104C09K2211/1029H10K85/657H10K50/00
Inventor 陈润锋徐申李欢欢黄维
Owner NANJING UNIV OF POSTS & TELECOMM
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