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Poly(arylene ether) compositions and the method for their manufacture

a technology of poly(arylene ether) and compositions, which is applied in the direction of instruments, semiconductor/solid-state device details, transportation and packaging, etc., can solve the problems of low yield of ethylnylated aromatic compounds produced therefrom, low yield, and high cost, and achieve low moisture absorption, high thermal stability, and low solubility.

Inactive Publication Date: 2002-03-19
ALLIEDSIGNAL INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The poly(arylene ether) compositions of this invention not only possess a Tg in excess of about 350.degree. C. without having to highly cross-link the compound or include cross-linkable pendent groups thereto as well as without sacrificing any of its other properties such as solubility, spin-coatability, high thermal stability, low moisture absorptivity, low dielectric constant, and planarizability.

Problems solved by technology

However, the yield of ethylnylated aromatic compounds produced therefrom is very low, i.e. 4% to 14%.
However, such methods are also laborious, costly, and low-yielding.

Method used

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  • Poly(arylene ether) compositions and the method for their manufacture
  • Poly(arylene ether) compositions and the method for their manufacture
  • Poly(arylene ether) compositions and the method for their manufacture

Examples

Experimental program
Comparison scheme
Effect test

example 1

Preparation of Coating Solution

After preparing a 12% solution of a poly(arylene ether) corresponding to formula C' wherein Z is 1,5-naphthalenediyl and n is about 10, available from Allied-Signal under the tradename "FLARE.TM. 1.51", by dissolving the appropriate quantity of the solid polymer in cyclopentanone under ambient conditions in a glass lined reactor, the solution was filtered through a series of four Teflon filtration cartridges at different pore sizes, i.e. 1.0, 0.5, 0.2 and 0.1 micrometers.

example 2

Preparation of Film Coated Substrate

About 3 ml to about 7 ml of the solution prepared in Example I was processed onto the surface of a silicon wafer having a diameter of 6 inches, using a spin coater manufactured by Silicon Valley Group, Inc. (SVG), Model No. 8826, and a multiple hot plate oven track manufactured by SVG, Model 8840, with the initial spin conditions set at 72.degree. F., 20-30 mmHg, and a spin cup humidity of 40%. The spin-bake-cure recipe was in accordance with the conditions set forth in "Lau".

Various thermomechanical and electrical properties of the film were measured as illustrated below in Table 1.

TABLE 1 PROPERTIES OF FLARE .TM. 1.51 POLYARYLENE ETHER FILM Poly(arylene ether) PROPERTY FLARE .TM. 1.51 Cured film thickness Nominally 1 micron Film Thickness Uniformity 350.degree. C. (DMA) 378.degree. C. (TMA) Residual Stress (stress hysteresis) 31-37 MPa Residual Stress (Bending Beam) 45 MPa CTE (ppm / .degree. C.) (TMA) 43-52 CTE (ppm / .degree. C.) (Bending Beam) 40...

example 3

Preparation of Free Standing Films

Fifty mL of the solution of Example 1 was concentrated to 25% solids content and then poured onto the surface of an optically polished quartz plate having a diameter of 10 cm to cover an area of about 1 cm by 6 cm. The solution was then leveled across the plate's surface with a doctor's blade set at a nominal setting, typically in the range of 35 .mu.m to 80 .mu.m, then baked on a hot plate. The coated plate was exposed to a variant temperature increasing at a rate of 5.degree. C. / min until the hot plate reached a temperature of 150.degree. C., at which point it was baked at a constant temperature for about 2 hours.

In order to cure the film, the baked coated plate was then heated, in the presence of nitrogen, inside the furnace chamber of a Tencor Flexus Model 2410 stress gauge at a variant temperature increasing at a rate of 5.degree. C. / min until the furnace reached a temperature of 425.degree. C., then heated for 1 hour at 425.degree. C., and the...

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Abstract

A method is disclosed for making hydroxy-substituted ethynylated biphenyl compounds and for reacting such compounds with a family of noncross-linking thermosetting poly(arylene ethers) to produce novel poly(arylene ether) compositions which, when cured at glass transition temperatures greater than about 350° C. to form thin films, possess properties such as low dielectric constant, low moisture absorption, and high thermal stability. These films are suitable for use as intermetal dielectrics for multilevel interconnection.

Description

BACKGROUND OF THE INVENTION1. Field of the InventionThe present invention relates to fluorinated poly(arylene ether) compositions for use in coating microelectronic structures, such as integrated circuits, and the method for their manufacture. More particularly, this invention relates to the use of novel bisphenol reactants in the method of manufacturing novel poly(arylene ether) compositions which possess improved properties such as higher glass transition temperature and lower dielectric constant.2. Background of the InventionFluorinated poly(arylene ethers) based upon decafluorobiphenyl have been used extensively as replacements for polyimides for use in spin-coating substrates, such as multichip modules, printed circuit boards, integrated circuits and other microelectronic devices in intermetal dielectric production. These fluorinated poly(arylene ethers), which are commercially available from AlliedSignal Inc. under the tradename "FLARE.TM.", not only exhibit a thermal stabilit...

Claims

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Application Information

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IPC IPC(8): C08G65/40C08G65/00H01L23/52H01L23/532H01L21/56H01L23/29H01L23/31
CPCC08G65/4006H01L23/5329C08G2650/48C08G2650/60Y10T428/24917Y10S428/901Y10T428/24802H01L2924/0002Y10T428/3154H01L2924/00C08G65/40H01L23/29H01L23/498
Inventor LAU, KREISLERHENDRICKS, NEILWAN, WILLIAMSMITH, AARON
Owner ALLIEDSIGNAL INC
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