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Single-borinine heterocycle organic electron transportation material and preparation method thereof

A technology for transport materials and organic electronics, which is applied in the field of single boron heterocyclic organic electron transport materials and its preparation, and can solve the problems of low electron transport efficiency and low performance of organic light-emitting devices

Active Publication Date: 2013-12-18
TAICANG BIQI NEW MATERIAL RES & DEV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the electron transport efficiency of the above compounds is not high, resulting in low performance of organic light-emitting devices

Method used

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  • Single-borinine heterocycle organic electron transportation material and preparation method thereof
  • Single-borinine heterocycle organic electron transportation material and preparation method thereof
  • Single-borinine heterocycle organic electron transportation material and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Under nitrogen protection, in a three-necked flask, dissolve 0.1mol of 6-chloro-6,13-dihydronaphtho[2,3-b:2',3'-e]borane and 0.001mol of palladium acetate in 50mL In anhydrous tetrahydrofuran, cool to -78°C, add dropwise 60mL of 1M phenyl lithium hexane solution, dropwise, stir, continue to react for 24 hours, raise the temperature to 25°C, add 200mL of chloroform and 100mL of water, separate the liquid, and the organic layer Dry over anhydrous sodium sulfate, filter, concentrate, and purify the solid by vacuum sublimation to obtain the organic electron transport material 6-phenyl-6,13-dihydronaphtho[2,3-b:2',3'-e ] Bora ring (A), yield: 56%, melting point: >300℃, elemental analysis: C, 91.54; H, 5.41; B, 3.05, calculated value C, 91.51; H, 5.43; B, 3.06, mass spectrum Test: m / z: 354 (100.0%).

Embodiment 2

[0040] Under nitrogen protection, in a three-necked flask, dissolve 0.1mol of 6-chloro-6,13-dihydronaphtho[2,3-b:2',3'-e]borane and 0.001mol of palladium acetate in 50mL In anhydrous tetrahydrofuran, cool to -78°C, add dropwise 60mL of 1M 2-methylphenyllithium hexane solution, dropwise, stir, continue to react for 24 hours, heat up to 25°C, add 200mL of chloroform and 100mL of water, divide liquid, the organic layer was dried with anhydrous sodium sulfate, filtered, concentrated, and the solid was purified by vacuum sublimation to obtain the organic electron transport material 6-(2-methylphenyl)-6,13-dihydronaphtho[2,3 -b:2',3'-e]boracyclic ring (B), yield: 27%, melting point: >300℃, elemental analysis: C,91.41; H,5.70; B,2.89, calculated value C,91.32 ; H, 5.75; B, 2.94, mass spectrometry: m / z: 368 (100.0%).

Embodiment 3

[0042] Under nitrogen protection, in a three-necked flask, dissolve 0.1mol of 6-chloro-6,13-dihydronaphtho[2,3-b:2',3'-e]borane and 0.001mol of palladium acetate in 50mL In anhydrous tetrahydrofuran, cool to -78°C, add dropwise 60mL of 1M 3-methylphenyl lithium hexane solution, dropwise, stir, continue to react for 24 hours, heat up to 25°C, add 200mL of chloroform and 100mL of water, divide liquid, the organic layer was dried with anhydrous sodium sulfate, filtered, concentrated, and the solid was purified by vacuum sublimation to obtain the organic electron transport material 6-(3-methylphenyl)-6,13-dihydronaphtho[2,3 -b:2',3'-e]boracyclic ring (C), yield: 31%, melting point: >300℃, elemental analysis: C, 91.38; H, 5.72; B, 2.90, calculated value C, 91.32 ; H, 5.75; B, 2.94, mass spectrometry: m / z: 368 (100.0%).

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Abstract

The invention belongs to the field of organic functional materials, and in particular relates to a single-borinine heterocycle organic electron transportation material and a preparation method thereof. The electron transportation material provided by the invention structurally comprises double-naphthyl, a single-borinine six-membered heterocycle and substituent aryl, and has the advantages that due to the existence of a B element in a molecular structure of the electron transportation material, electrons can be directly transported in conjugated aryl, the B element and an organic light emitting electronic device along a short path, so that the electron transportation material is high in electron transportation efficiency. The single-borinine heterocycle organic electron transportation material is prepared by taking 6-chlorine-6,13-dihydrodinaphtho[2,3-b:2',3'-e]borinine, aryl lithium and palladium acetate as initial raw materials through using a one-step method. A preparation process is simple.

Description

technical field [0001] The invention belongs to the technical field of organic functional materials, and in particular relates to a single boron heterocyclic organic electron transport material and a preparation method thereof. Background technique [0002] Organic electroluminescence is also called organic light-emitting diode (organic light-emitting diode), referred to as OLED, which is a research hotspot in the field of flat panel display in the world in recent years. This type of device has the advantages of simple structure, high yield and low cost; active light emission, fast response speed, high resolution, etc.; and low driving voltage, all solid-state, non-vacuum device, with shock resistance and low temperature resistance (-40 ℃) performance , is considered to be a new technology that is most likely to replace liquid crystal displays in the future, and has attracted great attention. At present, the research on OLED at home and abroad mainly focuses on the research...

Claims

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Application Information

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IPC IPC(8): C07F5/02
Inventor 蓝碧健
Owner TAICANG BIQI NEW MATERIAL RES & DEV
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