Benzocyclobutene substituted annular siloxane monomer as well as preparation method and application of benzocyclobutene substituted cyclic annular siloxane monomer

A technology of benzocyclobutene and cyclic siloxane, which is applied in the field of microelectronic packaging medium materials, can solve the problems of high curing temperature, poor flatness and high hygroscopicity, and achieves low water absorption, low dielectric constant, short time effect

Active Publication Date: 2011-06-15
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Polyimide (PI) is a commonly used MCM dielectric material, but it has high hygroscopicity (0.5%~1.7%), poor planarity, high curing temperature (greater than 280°C), and large shrinkage rate (about 25%). and other shortcomings

Method used

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  • Benzocyclobutene substituted annular siloxane monomer as well as preparation method and application of benzocyclobutene substituted cyclic annular siloxane monomer
  • Benzocyclobutene substituted annular siloxane monomer as well as preparation method and application of benzocyclobutene substituted cyclic annular siloxane monomer
  • Benzocyclobutene substituted annular siloxane monomer as well as preparation method and application of benzocyclobutene substituted cyclic annular siloxane monomer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Example 1 Synthesis of cyclotetrasiloxane BCB monomer: 4-bromobenzocyclobutene (15.1g, 0.083mol), tetramethyltetravinylcyclotetrasiloxane (7.05g, 0.02mol), Add triethylamine (15ml), acetonitrile (50ml), palladium acetate (334mg, 1.49mmol) and tris(o-methylphenyl)phosphine (750mg, 2.45mmol) into a 100mL three-necked flask, and rinse with nitrogen at room temperature for 30 Minutes later, heating and stirring were started, and the mixture was refluxed at 85°C for 24 hours. Finish the reaction, cool to room temperature, pour into 150mL 1mol / L hydrochloric acid aqueous solution, extract with 150mL (3*50mL) dichloromethane, wash the organic phase with water (5*150mL) until neutral. Dry over anhydrous magnesium sulfate overnight, filter, and remove the dichloromethane solution to obtain a brown-yellow oil. Silica gel column chromatography purification, eluent: petroleum ether (boiling range 60-90°C) / dichloromethane=10 / 1 (v / v), after vacuum distillation to remove the solvent,...

Embodiment 2

[0024]Example 2 Preparation of cyclotetrasiloxane BCB prepolymer: add the cyclotetrasiloxane BCB monomer (2.43g) synthesized in Example 1 into mesitylene (7.52g) solvent, Reflux at 170° C. for 24 hours, and cool to room temperature to obtain a prepolymer solution that can be directly used for spin coating film formation. Gel permeation chromatography analysis showed that the number average molecular weight of the prepolymer was 3596 g / mol, the weight average molecular weight was 4135 g / mol, and the molecular weight distribution was 1.150.

Embodiment 3

[0025] Example 3 Curing of cyclotetrasiloxane BCB: put the cyclotetrasiloxane BCB synthesized in Example 1 into a specific mold, and react according to the following conditions: 80°C / 1h, 150°C / 1h, 210°C / 1h, 240℃ / 1h, 250℃ / 1h, to obtain a cured resin with mechanical properties without pore distribution. IR(KBr, cm -1 ): 2958(s), 2925(s), 2827(s), 1604(s), 1570(m), 1500(s), 1437(s), 1261(vs), 1059(vs), 788(s ). Thermogravimetric analysis: the initial thermal decomposition temperature (1% weight loss) of the cured product of cyclotetrasiloxane BCB is 487.3°C, and the residual amount at 600°C is 65.1%.

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Abstract

The invention belongs to the technical field of micro-electronic packaging dielectric materials, particularly relates to a benzocyclobutene (BCB) substituted annular siloxane monomer as well as preparation and an application of the BCB substituted annular siloxane monomer. Annular vinyl siloxane and 4-benzocyclobutene are reacted in one step in the presence of a palladium catalyst so as to obtain a target monomer; and the monomer can be directly heated for polymerization forming, or the monomer also can be prepared into an organic solution of prepolymer and then spin film making is carried out on base plate materials such as metal, ceramic, silicon and the like. The preparation and use methods of the BCB substituted annular siloxane monomer are simple and convenient, the resins subjected to heat curing have the advantages of high stability, low dielectric constant, low dielectric loss, low water absorption and good film forming property, can be used as a high property dielectric material, and has wide application prospects in the fields of electronic packaging, system integration and the like.

Description

technical field [0001] The invention belongs to the technical field of microelectronic packaging dielectric materials, and specifically relates to a polybenzocyclobutene-substituted cyclic siloxane monomer, a preparation method and application thereof. Background technique [0002] With the continuous pursuit of lighter, thinner, smaller, high performance and low power consumption of electronic products, Multichip Module (MCM for short), Wafer Level Package (WLP for short), three-dimensional packaging And other advanced packaging technologies have been widely used in the manufacture of electronic components, thus greatly reducing the volume of electronic systems, reducing weight and improving reliability. The core of MCM technology is the multi-layer wiring on the packaging substrate, in which the insulating medium is a very critical material, which determines the performance and reliability of the MCM to a large extent. Polyimide (PI) is a commonly used MCM dielectric mate...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): H01L23/31C07F7/21C08G77/20
Inventor 杨军肖斐
Owner FUDAN UNIV
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