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Phenyl anthracene silole derivative organic optoelectronic material and synthetic method thereof

An organic optoelectronic material and a synthesis method technology, applied in the field of chemistry, to achieve the effects of high catalytic activity and yield, good electroluminescence performance, and easy conditions

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

AI Technical Summary

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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  • Phenyl anthracene silole derivative organic optoelectronic material and synthetic method thereof
  • Phenyl anthracene silole derivative organic optoelectronic material and synthetic method thereof
  • Phenyl anthracene silole derivative organic optoelectronic material and synthetic method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0021] Example 1, the synthesis method of 1,2-diphenyl-5,8-dipropyl-6,7-dicarboxylic acid dimethyl ester-14,14-dimethyl-14 silfluorenone naphthalene, the 1, The structural formula of 2-diphenyl-5,8-dipropyl-6,7-dicarboxylic acid dimethyl ester-14,14-dimethyl-14 silfluorenonenaphthalene is shown in formula (1-10), which The synthetic method comprises the following steps:

[0022] Step 1, preparation of phenylethynyl-(2-phenylethynyl)phenylsilane

[0023] Under nitrogen protection, 78mg (0.11mmol) bis(triphenylphosphine)-palladium dioxide, 1.06g (3.75mmol) o-bromoiodobenzene, 25mL triethylamine, 24mg (0.13mmol) CuI and 0.383g (3.75mmol) of phenylacetylene shown in structural formula (1-1), stirred at room temperature for 24h, filtered, the filtrate was extracted with ether, washed with water, dried, and rotary evaporated, and carried out column chromatography separation with pure n-hexane as the developing agent, 0.62 g (yield 64.3%) of 1-bromo-2-phenylethynylbenzene was obtai...

Embodiment 2

[0046] Example 2: Synthesis method of 1,5,8,12-tetraphenyl-6,7-dicarboxylic acid dimethyl-14,14-dimethylsilfluorenone naphthalene, the 1,5,8,12- The structural formula of tetraphenyl-6,7-dimethyl dimethyl-14,14-dimethylsilafluorene naphthalene is shown in formula (2-10), and its synthesis method comprises the following steps:

[0047] Step 1, preparation of phenylethynyl-(2-phenylethynyl)phenylsilane

[0048] Under nitrogen protection, add 316mg (0.45mmol) bis(triphenylphosphine)-palladium dioxide to 250mL reaction tube, 4.24g (15mmol) o-bromoiodobenzene, 100mL triethylamine, 95mg (0.5mmol) CuI, 1.532 g (15mmol) of phenylacetylene shown in structural formula (1-1), stirred at room temperature for 20h, filtered, the filtrate was extracted with ether, washed with water, dried, rotary evaporated, separated by column chromatography (developing agent is pure n-hexane), and 2.573 g (66.7% yield) 1-bromo-2-phenylethynylbenzene. The structural formula of the 1-bromo-2-phenylethynylb...

Embodiment 3

[0066] Example 3, the synthesis method of 1,2-diphenyl-5,8-dipropyl-6,7-dicarboxylic acid dimethyl ester-14,14-dimethyl-14 silfluorenone naphthalene, the 1, The structural formula of 2-diphenyl-5,8-dipropyl-6,7-dicarboxylic acid dimethyl ester-14,14-dimethyl-14 silfluorenonenaphthalene is shown in formula (1-10), which The synthetic method comprises the following steps:

[0067] Step 1, preparation of phenylethynyl-(2-phenylethynyl)phenylsilane

[0068] Under nitrogen protection, add 0.383mg (0.446mmol) bis(triphenylphosphine)-palladium dioxide, 4.24g (15mmol) o-bromoiodobenzene, 100mL triethylamine, 95mg (0.51mmol) CuI, into a 250mL reaction tube, 1.683g (16.48mmol) phenylacetylene, its structural formula is as shown in formula (1-1), stirred at room temperature for 22h, filtered, the filtrate was extracted with ether, washed with water, dried, rotary evaporated, separated by column chromatography (developing agent is pure n-hexane ), yielding 2.86 g (74.2%) of 1-bromo-2-ph...

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Abstract

The invention discloses a phenyl anthracene silole derivative organic optoelectronic material; with use of a catalytic action of a metallocene zirconium complex and butyl lithium on olefin polymerization, phenylsilane is synthesized through an anhydrous and anaerobic reaction; a silafluorene compound is synthesized by using CuCl catalytic action; with use of reduction of LiAlH4, an ester group is reduced into hydroxyl; the phenyl anthracene silole derivative organic optoelectronic material is synthesized by using DDQ oxidation. Compared with a general organic optoelectronic material, phenyl anthracene silole derivative parallel rings are increased, a pi-conjugated system is bigger, and the organic optoelectronic material has better electroluminescent properties in theory. In the synthesis process, o-bromo iodobenzene is used as a raw material, and silicon-bridged diyne is synthesized; zirconium induces a cycloaddition reaction for generating alkyne from silicon-bridged diyne, the conditions are easy to achieve, the time is short, and the yield is high. Compared with a conventional synthesis method of corresponding materials, the method adopts butyl lithium and the zirconocene complex for catalysis, has higher catalytic activity and yield, and has the used raw materials cheaper and easier to obtain.

Description

technical field [0001] The invention belongs to the field of chemistry and relates to an organic photoelectric material, in particular to an organic photoelectric material of benzene and anthrazosilole derivatives 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. The silole derivatives containing silicon heterocyclic rings have good redox stability due to their special structure, and they have relatively high hole transport rate and electron transport rate. However, the incorporation of benzene and naphthalene on both sides of silole, and the construction of silicon-bridged acene biphenyl by ring augmentation are difficult to solve in the synthesis. There are few reports on the synthesis of silafluorene molecules, and the synthesis method...

Claims

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Application Information

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IPC IPC(8): C07F7/08C09K11/06H01L51/00
CPCC09K11/06C07F7/0816C07F7/083C09K2211/1096H10K85/40
Inventor 曲红梅张昕李君秋陈旭种泽鹏
Owner TIANJIN UNIV
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