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Functionalized organosilicon compound containing benzocyclobutene, and preparation method thereof

A benzocyclobutene functional, organosilicon compound technology, applied in the field of polymer materials, can solve complex problems

Active Publication Date: 2017-06-20
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] The raw materials required by this method, especially silazane, need to be synthesized in multiple steps, which is relatively complicated.

Method used

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  • Functionalized organosilicon compound containing benzocyclobutene, and preparation method thereof
  • Functionalized organosilicon compound containing benzocyclobutene, and preparation method thereof
  • Functionalized organosilicon compound containing benzocyclobutene, and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Example 1. Using methylvinylbenzocyclobuten-4-ylchlorosilane and adamantanediol to react to prepare adamantane-containing benzocyclobutene organosilicon compound

[0047] 1,4-adamantanediol (1.682g, 10 mmol), 10ml of tetrahydrofuran, imidazole (1.80g, 26.4mmol), DMAP (0.122g, 1.0 mmol) were added to the three-necked flask, the methyl vinyl benzo Cyclobuten-4-ylchlorosilane (4.593g, 22mmol) and 5ml tetrahydrofuran were added to the constant pressure dropping funnel. Slowly add the mixed solution of methyl vinyl benzocyclobuten-4-yl chlorosilane and tetrahydrofuran to a three-necked flask at room temperature. A white precipitate immediately formed in the reaction solution. After the dropping, the reaction was continued for 2 hours. After the reaction, add ethyl acetate (30ml*3) for extraction, wash the organic layer with deionized water (30ml*2), and dry with anhydrous magnesium sulfate. After filtration, the solvent was removed by rotary evaporation, and purified by dist...

Embodiment 2

[0049] Example 2. Using methyl vinyl BCB chlorosilane to react with 1,4-bis(hydroxydimethylsilyl)benzene to prepare a phenylene-containing structural benzocyclobutene organosilicon compound

[0050] Add 1,4-bis(hydroxydimethylsilyl)benzene (0.6g, 3.5mmol), 10ml tetrahydrofuran, into a three-necked flask, add methylvinylbenzocyclobuten-4-ylchlorosilane (1.4 g, 7mmol), 1.2ml triethylamine, and 5ml tetrahydrofuran were added to the constant pressure dropping funnel. Slowly add methyl vinyl benzocyclobuten-4-yl chlorosilane, triethylamine and tetrahydrofuran mixed solution to the three-necked flask at room temperature. A white precipitate immediately formed in the reaction solution. After the dropping, the reaction was continued for 2 hours. After the reaction, add ethyl acetate (30ml*3) for extraction, wash the organic layer with deionized water (30ml*2), and dry with anhydrous magnesium sulfate. After filtration, the solvent is removed by rotary evaporation, and purified by dist...

Embodiment 3

[0052] Example 3. Using methyl vinyl BCB chlorosilane and 1,4-bis (hydroxydimethylsilyl) biphenyl to prepare biphenylene-containing structural benzocyclobutene organosilicon compound

[0053] Add 1,4-bis(hydroxydimethylsilyl)biphenyl (2.12g, 7mmol), 2.4ml triethylamine, 20ml tetrahydrofuran, into a three-necked flask, add methylvinylbenzocyclobutene-4 -Base chlorosilane (2.8g, 14mmol), 5ml tetrahydrofuran were added to the constant pressure dropping funnel. Slowly add a mixed solution of methyl vinyl benzocyclobuten-4-yl chlorosilane and tetrahydrofuran to a three-necked flask at room temperature. A white precipitate immediately formed in the reaction solution. After the dropping, the reaction was continued for 2 hours. After the reaction, add ethyl acetate (30ml*3) for extraction, wash the organic layer with deionized water (30ml*2), and dry with anhydrous magnesium sulfate. After filtration, the solvent is removed by rotary evaporation, and purified by distillation under re...

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Abstract

The invention belongs to the technical field of polymer materials, and concretely relates to a functionalized organosilicon compound containing benzocyclobutene, and a preparation method thereof. The functionalized organosilicon compound containing the benzocyclobutene is prepared through reacting an organosilicone precursor containing the benzocyclobutene and a substrate containing hydroxyl under an alkaline condition, and can be subjected to reduced pressure distillation or column chromatography purification. The functionalized organosilicon compound containing the benzocyclobutene can be used for polymerization reaction, and can be pre-polymerized in a sym-trimethylbenzene solvent at the temperature of 150 to 180 DEG C to obtain a prepolymer with a certain molecular weight, and a thin film is prepared through further spin-coating and post curing; a nitrine type photosensitizer can be added in a monomer prepolymer containing double bonds so as to be used for preparing a photoresist, which can be applied in the fields of electronic packaging and integrated circuits.

Description

Technical field [0001] The invention belongs to the technical field of polymer materials, and specifically relates to a functionalized organosilicon compound containing benzocyclobutene and a preparation method thereof. Background technique [0002] Benzocyclobutene is an excellent polymer material. After the benzocyclobutene monomer is heated, it can undergo ring-opening polymerization to form a highly crosslinked, low-dielectric polymer material. Since the introduction of the benzocyclobutene functional group is usually introduced by methods such as Heck reaction, a palladium precious metal catalyst is required, and the post-processing is relatively complicated. For example, the Cyclotene series of benzocyclobutene resin monomers developed by The Dow Chemical Company have the following chemical structure: [0003] [0004] Cheng Yuanrong, Kong Lingqiang, Xiao Fei et al. disclosed a series of benzocyclobutene monomers containing adamantane structure in a patent (application numbe...

Claims

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Application Information

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IPC IPC(8): C07F7/18C07F7/08C08G77/04C09J183/04
CPCC07F7/0838C07F7/0874C07F7/1804C07F7/188C08G77/04C09J183/04
Inventor 程元荣肖斐陈文豪魏晓燕朱倘维张子榆
Owner FUDAN UNIV
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