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Boron-nitrogen heteropolyaromatic ring compound and application thereof

An aromatic ring compound and heteropoly technology, which is applied in the fields of compounds containing Group 3/13 elements of the periodic table, organic chemistry, chemical instruments and methods, etc., can solve the problems of low performance and luminous efficiency of OEL devices, energy level, charge The mobility stability is difficult to achieve a good unity, and the glass transition temperature is low.

Pending Publication Date: 2020-08-11
南京知研科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

4,4'-bis(9-carbazole)biphenyl (CBP) is a widely used host material with good hole transport properties, but when CBP is used as a host material, due to its low glass transition temperature, It is easy to recrystallize, which makes it difficult to achieve good unity in terms of energy level, charge mobility, and stability, which leads to low performance and luminous efficiency of OEL devices. High efficiency, good stability, high luminous efficiency and performance host materials are the key to improving the performance of current OEL devices

Method used

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  • Boron-nitrogen heteropolyaromatic ring compound and application thereof
  • Boron-nitrogen heteropolyaromatic ring compound and application thereof
  • Boron-nitrogen heteropolyaromatic ring compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] This embodiment provides a boron azapolyaromatic ring compound, and the synthesis route of compound C-1 is as follows:

[0062]

[0063] The preparation method of compound C-1 specifically includes the following steps:

[0064] 1) Add 4-bromo-o-phenylenediamine (37.4g, 0.20mol), bromobenzene (66.0g, 0.42mol), toluene (500mL), and sodium tert-butoxide (84.6g, 0.88mol) in a three-necked flask. Add tri-tert-butyl phosphine (2.0mmol) under nitrogen protection, Pd 2 (dba) 3 .CHCl 3 (1.04g, 1.0mmol), the resulting solution was refluxed at 110°C for 8 hours, cooled to room temperature, filtered to obtain the filtrate and filter cake, the resulting filter cake was washed three times with toluene (100mL*3), and the washing solution and the filtrate were combined to obtain organic The organic phase was spin-dried, the solid obtained was purified with a silica gel column (eluent PE:EA=20:1 to 5:1), the eluent was spin-dried to obtain the product C-1-C (51.3g, yield 75.6 %).

[0065] 2)...

Embodiment 2

[0070] This embodiment provides an azapolyaromatic ring compound, and the synthesis route of compound C-2 is as follows:

[0071]

[0072] The preparation method of compound C-2 specifically includes the following steps:

[0073] 1) Add C-1-F (57.4g, 0.20mol), p-dibromobenzene (51.9g, 0.22mol), toluene (500mL), sodium tert-butoxide (38.4g, 0.40mol) in a three-necked flask, Add dppf (1,1'-bis(diphenylphosphine) ferrocene, 2.0mmol), Pd under the protection of nitrogen 2 (dba) 3 .CHCl 3 (1.04g, 1.0mmol), the resulting solution was refluxed at 110°C for 8 hours, cooled to room temperature, filtered to obtain the filtrate and filter cake, the resulting filter cake was washed three times with toluene (100mL*3), and the washing solution and the filtrate were combined to obtain organic The organic phase was spin-dried, the solid obtained was purified with a silica gel column (eluent PE:EA=30:1 to 15:1), the eluent was spin-dried to obtain the product C-2-A (68.2g, yield 85.6 %).

[0074] 2...

Embodiment 3

[0079] This embodiment provides an azapolyaromatic ring compound, and the synthesis route of compound C-4 is as follows:

[0080]

[0081] The preparation method of compound C-4 specifically includes the following steps:

[0082] 1) Add C-1-C (67.8g, 0.20mol) to toluene (400mL), add phenylboronic acid (24.4g, 0.20mol), the resulting solution is refluxed at 110°C for 3 hours, cooled, and the precipitated solid is filtered. The cake was washed with a small amount of toluene to obtain a crude product, and the crude product was vacuum-baked at 80°C for 8 hours to obtain the product C-4-A (79.0 g, yield 93.1%).

[0083] 2) Dissolve C-4-A (42.5g, 0.10mol) in a mixed solution of tetrahydrofuran (300mL) and water (75mL), add C-1-F (28.7g, 0.10mol), add potassium carbonate (27.6g) , 0.20mol), tetrakis(triphenylphosphine)palladium (500mg) was added under nitrogen protection, the resulting solution was refluxed for 8 hours, cooled to room temperature, and extracted with ethyl acetate (200mL*2)...

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Abstract

The invention relates to the technical field of display, in particular to a boron-nitrogen heteropolyaromatic ring compound and application thereof. The boron-nitrogen heteropolyaromatic ring compoundhas a structure as shown in a formula I, the compound is based on interaction between a boron-nitrogen structural unit and a surrounding aromatic ring or heteroaromatic ring. The boron-nitrogen heteropolyaromatic ring compound has higher glass transition temperature, higher and balanced charge mobility and more suitable single-triplet state energy, and when the boron-nitrogen heteropolyaromatic ring compound is used as a light-emitting main body material of an organic light-emitting device, the light-emitting efficiency of the device can be greatly improved, and the working voltage of the device is effectively reduced.

Description

Technical field [0001] The invention relates to the field of display technology, in particular to a boron azapolyaromatic ring compound and its use. Background technique [0002] Organic electroluminescence (OEL) devices (hereinafter referred to as "OEL" devices) have a series of advantages such as self-luminescence, high contrast, wide color gamut, wide viewing angle, and fast response. In 1963, Pope et al. first discovered the electroluminescence phenomenon of organic compounds. In 1987, Tang et al. of Kodak Corporation in the United States first successfully developed OEL devices using organic small molecule conductor materials, and achieved low voltage and high brightness luminescence performance. [0003] The current OEL device generally includes mutually opposed cathode and anode electrodes and one or more organic layers sandwiched between the two electrodes. Electrons and holes are injected into the organic layer from the anode and the anode respectively, and finally the or...

Claims

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Application Information

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IPC IPC(8): C07F5/02C09K11/06H01L51/54
CPCC07F5/02C09K11/06C09K2211/1085C09K2211/1033C09K2211/1055C09K2211/1088C09K2211/1044C09K2211/1029C09K2211/1092C09K2211/1007C09K2211/1011H10K85/615H10K85/6576H10K85/6574H10K85/6572H10K85/657
Inventor 孙魄
Owner 南京知研科技有限公司
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