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Full conjugation type monomer of dibenzo cyclobutene and preparation method

A technology of bisbenzocyclobutene and benzocyclobutene is applied to the new fully conjugated bisbenzocyclobutene monomer and the field of preparation thereof, and can solve the problems of low yield, unfavorable environmental protection and toxicity. Large and other problems, to achieve high yield, simple post-processing, good selectivity

Inactive Publication Date: 2005-01-12
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of these methods use toxic and expensive phosphine ligands, such as 1,2-bis(diphenylphosphine)ethane, which is not only unfavorable for environmental protection, but also has a low yield. Wherein R is 1 , 3-phenylene, the yield is only 22%

Method used

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  • Full conjugation type monomer of dibenzo cyclobutene and preparation method
  • Full conjugation type monomer of dibenzo cyclobutene and preparation method
  • Full conjugation type monomer of dibenzo cyclobutene and preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] In this example, monomer 4,4'-bisbenzocyclobutene was prepared by reaction under nitrogen atmosphere.

[0029] In a 500ml two-necked flask equipped with a magnetic stirring bar, first add 21mmol benzocyclobutene-4-boronic acid ethylene glycol 3.66g, 0.42mmol PdCl 2 75 mg, 1.05 mmol Bu 4 NBr 340mg, 20.4mmol 4-bromobenzocyclobutene 3.70g, 21mmol Na 2 B 4 o 7 10H 2 0.8.01g and absolute ethanol 300ml, then connect the nitrogen conduit and the condensation tube, after the logical nitrogen exhausted the air in the reaction flask, stirred at room temperature for 4 hours; the reaction solution was poured into 300ml water and mixed, and the mixed solution was extracted with sherwood oil ( 4×500ml), combined organic phase, anhydrous Na 2 SO 4 Dry, filter the organic phase with silica gel, rinse with petroleum ether, and concentrate the eluent to dryness under reduced pressure to obtain a colorless oily liquid. Recrystallize from petroleum ether to obtain 4,4'-bisbenzocyclo...

Embodiment 2

[0031] In this example, the monomer 4,4'-bisbenzocyclobutene was prepared by reacting in an air atmosphere.

[0032] In a 500ml round bottom flask equipped with a magnetic stirring bar, first add 21mmol benzocyclobutene-4-boronic acid 3.10g, 0.42mmol Pd(OAc) 2 95mg, 1.05mmolBu 4 NBr 340mg, 42mmol K 3 PO 4 ·3H 2 O 11.20g and absolute ethanol 300ml, stirred at room temperature in the air atmosphere for 24 hours; then the reaction solution was poured into 300ml water and mixed, and the mixed solution was extracted with petroleum ether (4 × 500ml); the organic phases were combined, anhydrous Na 2 SO 4 Dry, filter the organic phase with silica gel, rinse with petroleum ether, and concentrate the eluent to dryness under reduced pressure to obtain a colorless oily liquid. Recrystallize from petroleum ether to obtain 4,4'-bisbenzocyclobutene colorless transparent granular crystals 1.84 g, yield 85%.

Embodiment 3

[0034] In this example, the monomer 4,4'-bisbenzocyclobutene was prepared by reacting in an air atmosphere.

[0035] In a 500ml round bottom flask equipped with a magnetic stirring bar, first add 21mmol benzocyclobutene-4-diisopropyl borate 4.87g, 1.68mmol PdCl 2 298 mg, 2.10 mmol Bu 4 NCl 583mg, 16.2mmol 4-bromobenzocyclobutene 2.95g, 21mmol Na 2 CO 3 2.26g and 500ml of absolute ethanol, stirred at room temperature in an air atmosphere for 48 hours; then the reaction solution was poured into 500ml of water and mixed, and the mixed solution was extracted with petroleum ether (4 × 500ml); the organic phases were combined, anhydrous Na 2 SO 4 Dry, filter the organic phase with silica gel, rinse with petroleum ether, and concentrate the eluent to dryness under reduced pressure to obtain a colorless oily liquid. Recrystallize from petroleum ether to obtain 4,4'-bisbenzocyclobutene colorless transparent granular crystals 4.06 g, Yield >98%.

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Abstract

The characteristics is that this kind of monomer includes two new monomers. Benzo cyclobutane-4-boracic acid or the ester, or benzo cyclobutane-4-boracic acid or the ester and 4-bromo-benzo cyclobutane, or dihalogeno arene and benzo cyclobutane-4-boracic acid or the ester, or arylhypoboric acid or the ester and 4-bromobenzene cyclobutane are used as reaction material to be stirred with catalytic agent, inorganic alkali dissolvant more than 3 hours on room temp. in the air or nitrogen gas, then monomer I or / and monmer II is produced by a series of reprocessing.

Description

1. Technical field [0001] The invention belongs to the technical field of fully conjugated bisbenzocyclobutene monomer and its preparation, and in particular relates to a new fully conjugated bisbenzocyclobutene monomer and a preparation method thereof. 2. Background technology [0002] Polybenzocyclobutene resin is a large class of multifunctional materials, with excellent electrical properties such as low dielectric constant, low moisture absorption, low dielectric loss, excellent thermal stability and chemical stability, and is widely used in micro In the field of electronics industry, such as: VLSI multi-core mode electronic components (MCM technology) dielectric films, film materials for multimedia information carriers and micro-electrical systems (MEMS), etc. In addition, this type of resin has excellent processability, easy uniform film formation, and high flatness, generally greater than 95%, and can be directly polymerized on the surface of the device without produc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C2/86C07C15/24
Inventor 谢如刚杨军校陈文
Owner SICHUAN UNIV
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