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Silylated polyarylenes

An arylene and aryl technology, applied in the field of polyarylene materials, can solve problems such as incompatibility

Inactive Publication Date: 2016-06-22
ROHM & HAAS ELECTRONICS MATERIALS LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The polyphenylenes disclosed in U.S. Patent No. 5,965,679 have limited solubility in solvents commonly used in electronic device manufacturing, limiting the use of these polyphenylenes
In addition, these polyphenylenes have not been easily compatible with other materials used in electronic device manufacturing

Method used

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  • Silylated polyarylenes
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  • Silylated polyarylenes

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0036] Example 1: To a multi-neck round bottom flask with a stir bar was added via a powder funnel diphenylene oxide bis(triphenylcyclopentadienone) (DPO-CPD, 2.75 g, 3.52 mmol) followed by alkyne monomer 1, 3-Bis[(trimethylsilyl)ethynyl]benzene (1,3-TMS-DEB, 1.00 g, 3.70 mmol) and reaction solvent γ-butyrolactone (GBL, 20 g, 16% solids). The reaction was stirred gently at room temperature to obtain a homogeneous mixture. The flask was then equipped with a reflux condenser and an internal thermocouple probe attached to a self-regulating thermostat attached to a heating mantle. The dark maroon contents of the flask were warmed to an internal temperature of 205°C and maintained at this temperature for 96 hours, then cooled to room temperature by removing the heating element. The resulting dark maroon solution was transferred to a vial. Gel permeation chromatography on this crude mixture reveals that M n = 5362 Da and M w = Peak molecular weight distribution of 6678 Da.

[...

example 2

[0040] Example 2: The procedure of Example 1 was repeated except that the solvent was benzyl propionate.

example 3

[0041] Example 3: To a multi-neck round bottom flask with a stir bar was added diphenylene oxide bis(triphenylcyclopentadienone) (2.75 g, 3.52 mmol) followed by 1,3-bis[(trimethoxy silyl)ethynyl]benzene (1.36 g, 3.72 mmol) and the reaction solvent N-methylpyrrolidone (25 g). The reaction was stirred gently at room temperature to obtain a homogeneous mixture. The flask was then equipped with a reflux condenser and an internal thermocouple probe attached to a self-regulating thermostat attached to a heating mantle. The contents of the flask were warmed to an internal temperature of 195°C and maintained at this temperature for 96 hours before the heating element was removed.

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Abstract

Polyarylenes comprising as polymerized units a first monomer having two cyclopentadienone moieties and a second monomer having two or more alkyne moieties, wherein at least one alkyne moiety is directly bonded to a silicon atom are provided. Such polyarylenes are useful as dielectric materials in the manufacture of electronic devices.

Description

technical field [0001] The present invention relates generally to the field of polyarylene materials, and more particularly to polyarylene materials suitable for use as dielectric materials in the manufacture of electronic devices. Background technique [0002] Polymer dielectrics are used as insulating layers in a variety of electronic devices such as circuit boards, integrated circuits, electronic packaging, etc. One class of polymer dielectrics used in electronic device manufacture are polyarylenes, and polyphenylenes are particularly useful. U.S. Patent No. 5,965,679 discloses the Diels-Alder combination of a polyfunctional compound containing two or more cyclopentadienone groups and at least one polyfunctional compound containing two or more aromatic ethynyl groups. A polyphenylene polymer prepared by a Diels-Alder reaction, wherein at least some of the polyfunctional compounds contain three or more reactive groups. In this patent, "reactive groups" are defined as cyc...

Claims

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Application Information

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IPC IPC(8): C08G61/12
CPCC08G61/12C08G2261/344C08G2261/46C08G61/10C09D165/02C08L65/02C08G2261/135C08G2261/312C08G2261/364C08G2261/74C08G2261/76C08G2261/80B32B27/302C08G61/02C08L65/00B32B2457/00C08G2261/40C09D183/16C08G65/2639
Inventor C·D·吉尔摩P·丁Y·S·金T·H·金
Owner ROHM & HAAS ELECTRONICS MATERIALS LLC
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