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A kind of benzene, anthracenosilole derivative organic photoelectric material and its synthesis method

A technology of organic photoelectric materials and synthesis methods, applied in the field of chemistry, to achieve the effects of high yield, good electroluminescent performance, and easy conditions

Active Publication Date: 2019-04-16
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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  • A kind of benzene, anthracenosilole derivative organic photoelectric material and its synthesis method
  • A kind of benzene, anthracenosilole derivative organic photoelectric material and its synthesis method
  • A kind of benzene, anthracenosilole derivative organic photoelectric material and its synthesis method

Examples

Experimental program
Comparison scheme
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 an organic photoelectric material derived from benzene and anthrazosilole. A phenylsilane is synthesized through an anhydrous and oxygen-free reaction by utilizing the catalytic effect of metal zirconocene complexes and butyllithium on olefin polymerization; Catalysis of CuCl to synthesize a silafluorene compound; using LiAlH 4 The reducing property of DDQ is used to reduce the ester group to hydroxyl group; a photoelectric material of benzene and anthracenosilole derivatives is synthesized by using the oxidizing property of DDQ. Compared with general organic optoelectronic materials, the number of benzanthracene thiarolo rings is increased, and the π-conjugated system is larger, which in theory will have better electroluminescence performance. In the synthesis process, o-bromoiodobenzene is used as a raw material to synthesize a silicon-bridged diyne; zirconium induces a silicon-bridged diyne to form a cycloaddition reaction of an alkyne, the conditions are easy to achieve, the time is short, and the yield is high. Compared with the existing synthetic methods of corresponding materials, the catalytic activity and yield of the butyllithium and zirconocene complexes are higher, and the raw materials used are 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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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/08C09K11/06H01L51/00H10K99/00
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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