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Benzene and naphtho-silole derivative organic photoelectric material and preparation method thereof

A technology of organic photoelectric materials and naphthalene derivatives, which is applied in the chemical field to achieve the effects of mild conditions, low energy consumption and high yield

Active Publication Date: 2017-03-29
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The present invention aims to overcome the shortcomings of the existing synthesis methods and provide a novel organic optoelectronic material and its preparation method

Method used

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  • Benzene and naphtho-silole derivative organic photoelectric material and preparation method thereof
  • Benzene and naphtho-silole derivative organic photoelectric material and preparation method thereof
  • Benzene and naphtho-silole derivative organic photoelectric material and preparation method thereof

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Experimental program
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Effect test

Embodiment 1

[0022] Embodiment 1: prepare a kind of benzene, naphthosilole derivative organic photoelectric material, the steps are as follows:

[0023] Step 1. Preparation of 1,4-dibromo-2,5-diiodobenzene: Add 2.66g (11.7mmol) of periodic acid into a 250mL reaction flask, cool down to 0°C, and add 60mL of concentrated sulfuric acid. After stirring, 5.82g (35.1mmol) of potassium iodide was added, and after 15 minutes, 5.52g (23.4mmol) of p-dibromobenzene and 24mL of concentrated sulfuric acid were added successively, and the reaction was carried out at 0°C for 12 hours. Gradually rise to room temperature and react for 10 hours. Pour the reaction solution in the bottle into ice, stir, and filter the obtained filter cake, which is the crude product of 1,4-dibromo-2,5-diiodobenzene, dissolve the filter cake in chloroform, wash with dilute NaOH solution, and extract , the organic phase was dried, concentrated, and recrystallized to obtain 7.87g (yield 69%) of 1,4-dibromo-2,5-diiodobenzene. Th...

Embodiment 2

[0035] Embodiment 2: Prepare a kind of benzene, naphthosilole derivative organic photoelectric material, the steps are as follows:

[0036] Step 1. Preparation of 1,4-dibromo-2,5-diiodobenzene: Add 6.82g (30mmol) of periodic acid into a 1000mL reaction flask, cool down to 0°C, and add 150mL of concentrated sulfuric acid. After stirring, 14.92g (90mmol) of potassium iodide was added, and after 15 minutes, 14.15g (60mmol) of p-dibromobenzene and 60mL of concentrated sulfuric acid were added successively, and the mixture was reacted at 0°C for 10 hours. Gradually rise to room temperature and react for 8 hours. Pour the reaction solution in the bottle into ice, stir, and filter the obtained filter cake, which is the crude product of 1,4-dibromo-2,5-diiodobenzene, dissolve the filter cake in chloroform, wash with dilute NaOH solution, and extract , the organic phase was dried, concentrated, and recrystallized to obtain 16.67g (57% yield) of 1,4-dibromo-2,5-diiodobenzene. The solve...

Embodiment 3

[0042] Embodiment 3: Prepare a kind of benzene, naphthosilole derivative organic photoelectric material, the steps are as follows:

[0043] Step 1. Preparation of 1,4-dibromo-2,5-diiodobenzene: Add 2.66g (11.7mmol) of periodic acid into a 250mL reaction flask, cool down to 0°C, and add 60mL of concentrated sulfuric acid. After stirring, 5.82g (35.1mmol) of potassium iodide was added, and after 15 minutes, 5.52g (23.4mmol) of p-dibromobenzene and 24mL of concentrated sulfuric acid were added successively, and the reaction was carried out at 0°C for 18 hours. Gradually rise to room temperature and react for 15 hours. Pour the reaction solution in the bottle into ice, stir, and filter the obtained filter cake, which is the crude product of 1,4-dibromo-2,5-diiodobenzene, dissolve the filter cake in chloroform, wash with dilute NaOH solution, and extract , the organic phase was dried, concentrated, and recrystallized to obtain 8.326g (yield 73%) of 1,4-dibromo-2,5-diiodobenzene. T...

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Abstract

The invention discloses a benzene and naphtho-silole derivative organic photoelectric material and a preparation method thereof. The preparation method mainly comprises the steps that 1,4-dibromo-2,5-diiodobenzene, a naphthalene derivative, an alkynyl naphthalene derivative, a silicon naphthalene derivative and a silicon-bridged diyne derivative are sequentially prepared; and a finally prepared benzene and naphtho-silole derivative is the organic photoelectric material. Cyclopentadiene zirconacycles is synthesized through the lithiation effect of n-butyllithium; a naphthalene substitute is synthesized through the catalytic effect of CuCl; a silicon substitute is synthesized through the catalytic effect of PdCl2(PPh3)2 and the lithiation effect of n-butyllithium; silicon-bridged diyne is synthesized through the lithiation effect of n-butyllithium; and the benzene and naphtho-silole derivative is synthesized through the catalytic effect of CuCl. The synthesization process is mild in condition, short in reaction time and low in energy consumption, the raw materials are easy to obtain, and finally, the benzene and naphtho-silole derivative is obtained with the high yield in short reaction time.

Description

technical field [0001] The invention belongs to the field of chemistry and relates to an organic photoelectric material, in particular to a benzene and naphthosilole derivative organic photoelectric material and a synthesis method thereof. Background technique [0002] Organic optoelectronic materials are a class of organic materials with optoelectronic activity, which are widely used in organic light-emitting diodes, organic transistors, organic solar cells, organic memories and other fields. Silole is a kind of silicon-containing five-membered ring diene, which has good electron affinity, unique aggregation-induced luminescence properties and excellent electroluminescent properties. Polycyclic ladder π-conjugated molecules containing silole rings have attracted much attention in the field of organic optoelectronics due to their high fluorescence efficiency and high carrier transfer efficiency. However, there are few reports on silicon-bridged biphenyls, the yield is extre...

Claims

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Application Information

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IPC IPC(8): C07F7/08C09K11/06
CPCC07F7/0816C07F7/083C09K11/06C09K2211/1096
Inventor 曲红梅张昕李君秋陈旭
Owner TIANJIN UNIV
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