Unlock instant, AI-driven research and patent intelligence for your innovation.

Polymeric compositions comprising per(phenylethynyl) arene derivatives

a technology of phenylethyl and isne derivatives, which is applied in the direction of solid-state devices, basic electric elements, semiconductor devices, etc., can solve the problems of difficult to solve polymeric thermoset systems, art has not managed to solve problems,

Active Publication Date: 2013-02-12
VERSUM MATERIALS US LLC
View PDF16 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the need for materials compatibility and dimensional stability over a wide range of conditions not only during ultimate end use, but also during further processing conditions leading to the finished integrated circuits, have presented significant problems.
One of the problems has been to make a polymeric thermoset system.
This problem has been a difficult one to solve, particularly for those high Tg polymers wherein the desired temperature for reaction (cure) may range from 200-450° C.
However, despite various attempts to provide appropriate crosslinking of polymers for these application, the art has not managed to solve the problem of providing polymeric materials that fulfill at least one of the following requirements: improved coefficient of thermal expansion (CTE), improved hardness, improved adhesion resistance wherein one or all of these requirements is achieved without a significant loss of substrate adhesion, thermal stability, or both.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Examples

Experimental program
Comparison scheme
Effect test

example 1

Preparation of the Per(phenylethynyl)arene polymer 1,2,4,5-tetra(phenylethynyl)benzene

[0070]

[0071]A three-necked, glass reaction vessel is fitted with a thermometer, magnetic stir bar, condenser, static nitrogen inlet, and addition funnel then charged with 9.00 grams (g) (0.0229 mol) of 1,2,4,5-tetrabromobenzene, 0.2232 g (0.318 mmol) of bis(triphenylphosphine)palladium (II) chloride, 0.1668 g (0.636 mmol) of triphenylphosphine, 0.1211 g (0.636 mmol) of copper (I) iodide, and 180 g of triethylamine. The solution was heated to 70° C. with stirring. A solution of 9.34 g (0.0914 mol) of phenylacetylene and 50 g of triethylamine was then added drop-wise over the course of 2 hours. The addition rate was such that the temperature of the reaction mixture did not exceed 80° C. After complete addition, the reaction mixture was stirred for an additional 17 hours at 80° C. The reaction mixture is then cooled to room temperature and the precipitate is removed via filtration. The filter cake is ...

example 2

Preparation of Polymeric Composition comprising PAE-2 and 1,2,4,5-tetrakis(phenylethynyl)

[0072]0.2999 g of PAE-2 and 0.2008 g of 1,2,4,5-tetrakis(phenylethynyl) prepared in accordance with Example 1 were combined in ˜15 mL of tetrahydrofuran and dried briefly at 100° C. on a hotplate, followed by overnight at 120° C. in an oven. The residue was subjected to 220° C. in nitrogen atmosphere for 30 minutes (10 C / min ramp), which resulted in a weight loss of 1.24%, then cooled and reheated to 400° C. at 10° C. / minute and held at 400° C. for 120 minutes. The residue had 3.42% weight loss at 400° C. isothermal. The DSC showed a melt endotherm at 185° C. and a two peak exotherm at ˜305° C. and 390° C. on the first heat. The second heat was predominantly featureless, indicating crosslinking had occurred, and an interpenetrating network had formed.

example 3

Adhesion Results for Polymeric Composition comprising PAE-2 and 1,2,4,5-tetrakis(phenylethynyl)benzene

[0073]A solution was prepared from 1,2,4,5-tetrakis(phenylethynyl)benzene and PAE-2 (prepared in accordance with Example 2) was as follows:

[0074]

[0075]A 0.3997 g portion of 1,2,4,5-tetrakis(phenylethynyl)benzene and 0.6003 g of the poly(arylene ether) PAE-2 were dissolved in 9.0 g of distilled cyclohexanone. The solution was applied to six 1″×4.25″×0.32″ cold roll steel coupons provided by Act Laboratories Inc., Part #APR14839. The coupons were overlapped to form three test pieces with 0.5 sq. inch overlap area. All three pieces were heated to 400° C. and held at temperature for 10 minutes with a 10 lb. weight resting on each piece. The three pieces were subjected to Lap Shear Analysis, ASTM method D-1002 (metal). The results of this analysis are provided in the Table II below. The results show good adhesion for the cured polymer matrix to the steel substrate.

[0076]

TABLE IIStress at...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
temperatureaaaaaaaaaa
temperaturesaaaaaaaaaa
temperaturesaaaaaaaaaa
Login to View More

Abstract

A polymeric composition comprising a first polymer chosen from a poly(arylene ether) polymer including polymer repeat units of the following structure: —(O—Ar1—O—Ar2—O—)m—(—O—Ar3—O—Ar4—O)n- where Ar1, Ar2, Ar3, and Ar4 are identical or different aryl radicals, m is 0 to 1, n is 1 m; a polysulfone, a polyimide, a poly(etherketone), a polyurea, a polyurethane, and combinations thereof and a second polymer comprising a per(phenylethynyl) arene polymer derivative. Cured films containing the polymer can exhibit at least one of the following properties: Tg from 160° C. to 180° C., a dielectric constant below 2.7 with frequency independence, and a maximum moisture absorption of less than 0.17 wt %. Accordingly, the polymer is especially useful, for example, in interlayer dielectrics and in die-attach adhesives.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS[0001]This patent application claims the benefit of provisional patent application U.S. Ser. No. 61 / 088,176, entitled “Polymeric Compositions Comprising Per(phenylethyntyl)arene Derivatives” filed Aug. 12, 2008, incorporated herein by reference.BACKGROUND[0002]Disclosed herein are polymeric compositions comprising a per(phenylethynyl) arene derivative that can be used, for example, in various electronic applications such as, but not limited to, three dimensional (3D) packaging for IC chip assemblies. Also disclosed are substrates comprising same.[0003]There is a need in the electronic fabrication industry for polymeric materials with materials of lower dielectric values for use as adhesives for 3D packaging of IC chip assemblies. However, the need for materials compatibility and dimensional stability over a wide range of conditions not only during ultimate end use, but also during further processing conditions leading to the finished integrated...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(United States)
IPC IPC(8): H01L23/29
Inventor BURGOYNE, JR., WILLIAM FRANKLINCONNER, MARK DAVIDNORDQUIST, ANDREW FRANCISCOLLINS, WILLIAM STEVEN
Owner VERSUM MATERIALS US LLC