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2-bromine-9,9-dimethyl silicon fluorene and synthesis method thereof

A technology of dimethylsilyl fluorene and a synthesis method, which is applied in the directions of silicon organic compounds and the like, can solve the problems of inability to expand kilogram-level mass production, dangerous reaction process, long production cycle, etc., and achieves low cost of raw materials, simple and convenient operation, The effect of short production cycle

Inactive Publication Date: 2019-06-21
西安欧得光电材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The purpose of the present invention is to overcome the above-mentioned deficiencies in the prior art, to provide a kind of 2-bromo-9,9-dimethylsilafluorene and its synthesis method, which overcomes 1 in the prior art: the existing production process only Research and development at the gram level cannot be expanded to mass production at the kilogram level; 2: There are many reaction steps, the production cycle is long, and the cost is high; 3: The reaction process is dangerous, flammable and explosive, etc.

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  • 2-bromine-9,9-dimethyl silicon fluorene and synthesis method thereof
  • 2-bromine-9,9-dimethyl silicon fluorene and synthesis method thereof

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specific Embodiment approach

[0024] It should be noted that the structures, proportions, sizes, etc. shown in this specification are only used to cooperate with the content disclosed in the specification for the understanding and reading of those familiar with this technology, and are not used to limit the conditions for the implementation of the present invention , any modification of structure, change of proportional relationship or adjustment of size shall still fall within the scope covered by the technical content disclosed in the present invention without affecting the effect and purpose of the present invention. .

[0025] At the same time, terms such as "upper", "lower", "left", "right", "middle" and "one" quoted in this specification are only for the convenience of description and are not used to limit this specification. The practicable scope of the invention and the change or adjustment of its relative relationship shall also be regarded as the practicable scope of the present invention without...

Embodiment 1

[0028] The invention discloses a synthesis method of 2-bromo-9,9-dimethylsilafluorene, which comprises the following steps:

[0029] Step 1) A coupling reaction between o-dibromobenzene and n-butyl lithium is used to generate 2,2'-dibromobiphenyl, wherein the molar ratio of o-dibromobenzene and n-butyl lithium is 1:0.48-0.55;

[0030] Step 2) Use the 2,2'-dibromobiphenyl generated in step 1) to react with bromine to generate 2,2',4-tribromobiphenyl, wherein 2,2'-dibromobiphenyl and bromine The molar ratio of the element is 1:1~1.5;

[0031] Step 3) The 2,2',4-tribromobiphenyl generated in step 2) reacts with dichlorodimethylsilane to generate 2-bromo-9,9-dimethylsilafluorene, wherein 2 , The molar ratio of 2',4-tribromobiphenyl to dichlorodimethylsilane is 1:1~1.3.

Embodiment 2

[0033] The invention discloses a synthesis method of 2-bromo-9,9-dimethylsilafluorene, which comprises the following steps:

[0034] Step 1) A coupling reaction between o-dibromobenzene and n-butyl lithium is used to generate 2,2'-dibromobiphenyl, wherein the molar ratio of o-dibromobenzene and n-butyl lithium is 1:0.48-0.55;

[0035] Step 2) Use the 2,2'-dibromobiphenyl generated in step 1) to react with bromine to generate 2,2',4-tribromobiphenyl, wherein 2,2'-dibromobiphenyl and bromine The molar ratio of the element is 1:1~1.5;

[0036] Step 3) The 2,2',4-tribromobiphenyl generated in step 2) reacts with dichlorodimethylsilane to generate 2-bromo-9,9-dimethylsilafluorene, wherein 2 , The molar ratio of 2',4-tribromobiphenyl to dichlorodimethylsilane is 1:1~1.3.

[0037] Preferably, the specific reaction steps of step 1) are: under the protection of argon in a four-neck flask, add o-dibromobenzene and tetrahydrofuran, and use an ethanol bath to cool down to -78°C while st...

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Abstract

The invention discloses 2-bromine-9,9-dimethyl silicon fluorene and a synthesis method thereof. The synthesis method comprises the following steps: step 1) carrying out coupling reaction between o-dibromobenzene and n-butyllithium to generate 2,2'-dibromobiphenyl, wherein the molar ratio of the o-dibromobenzene to the n-butyl lithium is 1:(0.48-0.55); step 2) carrying out bromination reaction between the 2,2'-dibromobiphenyl formed in step 1) and bromine to generate 2,2',4-tribromobiphenyl, wherein the molar ratio of 2,2'-dibromobiphenyl to the bromine is 1:(1-1.5); step 3) carrying out ring-closure reaction of the 2,2',4-tribromobiphenyl generated in step 2) and dichlorodimethylsilane to generate the 2-bromine-9,9-dimethyl silicon fluorene, wherein the molar ratio of the 2,2',4-tribromobiphenyl to the dichlorodimethylsilane is 1:(1-1.3).

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to 2-bromo-9,9-dimethylsilafluorene and a synthesis method thereof. Background technique [0002] Fluorene compounds have become star molecules in blue light materials because of their high fluorescence quantum efficiency, high thermal stability, and easy structure modification. However, the 9-position carbon atom of fluorene derivatives is easily oxidized to fluorenone at high temperature, which in turn causes long-wave emission, reducing color purity and luminous efficiency. [0003] Using Si atom to replace the 9-position C atom of fluorene can effectively suppress the long-wave emission, improve the stability of the compound, and obtain a blue light material with high color purity of silicon fluorene. 2-Bromo-9,9-dimethylsilafluorene has a small molecule and good solubility, and the asymmetric structure of the monobromine compound allows the compo...

Claims

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Application Information

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IPC IPC(8): C07F7/08
Inventor 任莺歌郭红梅张言峰刘英锋
Owner 西安欧得光电材料有限公司
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