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N-phenylcarbazole derivative and application thereof to electrophosphorescent device

A technology of phenylcarbazole and phosphorescent devices is applied in the application field of blue phosphorescent host materials in organic electrophosphorescent devices, and can solve the problems of low glass transition temperature, hindering wide application and low material stability, etc. The effect of device performance improvement, conjugation reduction, and high-efficiency electroluminescence performance

Inactive Publication Date: 2013-10-02
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the glass transition temperature of mCP is low, and the stability of the material itself is not high, which hinders its wide application.

Method used

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  • N-phenylcarbazole derivative and application thereof to electrophosphorescent device
  • N-phenylcarbazole derivative and application thereof to electrophosphorescent device
  • N-phenylcarbazole derivative and application thereof to electrophosphorescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Step 1: Add 4.00 grams of 3,6-dibromocarbazole and 3.20 grams of N-phenylcarbazole-3-boronic acid into a 50-ml flask, add catalyst Pd (PPh 3 ) 4 650mg, THF 42ml, 2M K 2 CO 3 The solution was 14 ml, refluxed under argon protection for 24 hours, extracted with dichloromethane after cooling, the organic layer was dried with anhydrous sodium sulfate and then spin-dried, passed through the column with dichloromethane / petroleum ether=1:5 (volume ratio), and spin-dried 4.70 g of 6-bromo-N,N-diphenyl-3,3'-biscarbazole were obtained by drying, with a yield of 83.7%.

[0038] Step 2: Add 4.0 grams of 6-bromo-N,N-diphenyl-3,3'-biscarbazole and 4.0 grams of cuprous cyanide into a 50 ml flask, add N,N-dimethylformamide 30 ml, reflux under argon protection for 24 hours, extract with dichloromethane after cooling, dry the organic layer with anhydrous sodium sulfate and spin dry, pass through the column with dichloromethane / petroleum ether=1:5 (volume ratio), spin dry 2.91 g of 6-c...

Embodiment 2

[0040] Step 1: 4.00 grams of 3-bromocarbazole and 3.20 grams of N-phenylcarbazole-3-boronic acid are added in a 50 ml flask, and catalyst Pd(PPh 3 ) 4 650mg, THF 42ml, 2M K 2 CO 3The solution was 14 ml, refluxed under argon protection for 24 hours, extracted with dichloromethane after cooling, the organic layer was dried with anhydrous sodium sulfate and then spin-dried, passed through the column with dichloromethane / petroleum ether=1:5 (volume ratio), and spin-dried 5.33 g of N,N-diphenyl-3,3'-biscarbazole were obtained by drying, and the yield was 88.6%.

[0041] Step 2: Add 4.00 g of N,N-diphenyl-3,3'-biscarbazole and 30 ml of N,N-dimethylformamide into a 50 ml flask, cool to about 0°C in an ice bath, and separate Add 4.00 g of 1,3-dibromo-5,5-dimethylhydantoin in batches, and keep the temperature below 5°C for 8 hours. The reaction mixture was poured into water, extracted with dichloromethane, washed with water, washed with saturated brine, dried with anhydrous sodium ...

Embodiment 3

[0044] Step 1: Add 4.00 grams of 1,3-dibromobenzene and 3.20 grams of N-phenylcarbazole-3-boronic acid into a 50-ml flask, add catalyst Pd(PPh 3 ) 4 650mg, THF 42ml, 2M K 2 CO 3 The solution was 14 ml, refluxed under argon protection for 24 hours, extracted with dichloromethane after cooling, the organic layer was dried with anhydrous sodium sulfate and then spin-dried, passed through the column with dichloromethane / petroleum ether=1:5 (volume ratio), and spin-dried 7.44 g of 1,3-bis(N-phenylcarbazol-3-yl)benzene were obtained by drying. The yield was 78.3%.

[0045] Step 2: Add 4.00 g of 1,3-bis(N-phenylcarbazol-3-yl)benzene and 30 ml of N,N-dimethylformamide into a 50 ml flask, cool in an ice bath to about 0°C, Add 4.00 g of 1,3-dibromo-5,5-dimethylhydantoin in batches, and keep the temperature below 0°C for 8 hours. The reaction mixture was poured into water, extracted with dichloromethane, washed with water, washed with saturated brine, dried with anhydrous sodium sulf...

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Abstract

The invention discloses an N-phenylcarbazole derivative with a structure as shown by the accompanying drawing and application thereof to electrophosphorescent devices, wherein A does not contain any group, or A is substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, or pyridyl / pyrazinyl; and R1 and R2 are hydrogen, diphenylphosphoryl, cyano group, 3-pyridyl, 4-pyridyl, 2-dibenzothienyl / furyl and 4-dibenzothienyl / furyl. The N-phenylcarbazole derivative disclosed by the invention has the advantages that the conjugate degree of main body materials can be effectively reduced, the molecular weight of compounds is increased, the doublet energy level and the glass transition temperature of the materials are improved to a certain extent, the polarity can be adjusted through electron-donating / electron-withdrawing groups, and compared with the performance of commonly used phosphorescent main body materials, the performance of phosphorescent OLED (Organic Light Emitting Diode) devices is effectively improved and the N-phenylcarbazole derivative can be widely used in the field of organic electroluminescence.

Description

technical field [0001] The invention belongs to the field of optoelectronic materials and application technology, and relates to derivatives with N-phenylcarbazole as the basic structural unit, connected and modified groups with different electronic characteristics through the meta-position of the carbazole benzene ring, and their blue phosphorescent main body Applications of materials in organic electrophosphorescent devices. Background technique [0002] Organic electroluminescence is a self-luminous device. By sandwiching a light-emitting layer between a pair of electrodes and applying a voltage, electrons injected from the cathode (first electrode) and holes injected from the anode (second electrode) recombine at the light-emitting center. Molecular excitons are formed, and upon returning to the ground state, the molecular excitons release energy to emit light. Organic electroluminescent devices have the characteristics of low voltage, high brightness, wide viewing angl...

Claims

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Application Information

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IPC IPC(8): C07D401/14C07D403/14C07D209/88C07D409/14C09K11/06H01L51/54
Inventor 廖良生蒋佐权崔林松
Owner SUZHOU UNIV
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