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Deposition of polymeric materials and precursors therefor

A technology of polymers and precursors, applied in metal material coating process, gaseous chemical plating, coating, etc., can solve the problems of uniformity of difficult adhesive layer, gasification and escape of residual solvents, etc.

Inactive Publication Date: 2008-02-13
BREWER SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Furthermore, the spinning technique is not the preferred method due to the difficulty in maintaining the uniformity of the resulting adhesive layer on 200 and 300 mm wafers and the risk of vaporization of residual solvents during subsequent thermal processing

Method used

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  • Deposition of polymeric materials and precursors therefor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] About 130 mg of iron powder (average particle size 10 microns) was mixed with 150 mL of chloroform and 130 mL of dichloromethane in a 1000 mL round bottom flask. The mixture was sonicated with a commercial sonicator for 20 minutes, and then 250 ml of dichloromethane and about 17.7 g of [2.2]paracyclophane were added. The whole mixture was stirred open to air with a stir bar and paddle for 2 hours. Gas chromatography of the crude reaction mixture showed 87% yield of 4-bromo[2.2]paracyclane.

[0045] The reaction mixture was washed sequentially with two 150 mL (each) portions of 10% (by weight) aqueous sodium bisulfate, one 150 mL portion of 1 M aqueous NaOH, and one 150 mL portion of saturated aqueous NaCl. After washing, the mixture was washed with anhydrous MgSO 4 dry. The remaining solvent was evaporated using a rotovap at a temperature of 40°C. The residue was recrystallized from hot (50°C) chloroform. Recrystallization had no significant effect on the purity of...

Embodiment 2

[0047] Just before use, 1,4-dioxane was distilled over excess sodium metal and benzophenone ketyl with a reflux condenser under nitrogen. Cesium carbonate was dried at 115°C for 12 hours in a nitrogen atmosphere. Ethynyl-triethylsilane, tris(dibenzylideneacetone)dipalladium(0), and tri-tert-butylphosphine were purchased and used directly.

[0048] Reaction compositions were prepared in 1.5 mL crimp-top vials, each with a magnetic stir bar. To each vial was provided about 0.05 mmol of 4-bromo[2.2]paracyclane prepared and purified as described in Example 1, 0.15 mmol of CsCO 3 , 0.08 mmol of ethynyl-triethylsilane, 0.33 ml of 0.0022N tris(dibenzylideneacetone) dipalladium (0) solution in distilled dioxane, 0.33 ml of 0.188M tri-tert-butyl A solution of phosphine in distilled 1,4-dioxane, and 0.33 mL of a 0.137M solution of tri-tert-butylphosphine in distilled 1,4-dioxane. The sample was heated at 95°C for 3 hours under stirring with a magnetic stir bar. After separation and ...

Embodiment 3

[0050] A solution of 5.0 mmol of 4-(ethylsilaneethynyl)[2.2]p-cycloarane (prepared and purified according to Example 2) in 50 ml of tetrahydrofuran (HPLC grade) was prepared. To this solution was added 10.0 mL of 1.0 M Bu 4 n A solution of NF in THF. The unheated reaction mixture was stirred with a magnetic stir bar under nitrogen atmosphere for about 16 hours. THF was evaporated using a rotary evaporator. According to gas chromatography, the residue was 90% by weight of 4-ethynyl[2.2]paracyclophane.

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Abstract

Substituted paracyclophanes are particularly useful as precursors in the formation of a cross-linkable polymer on a deposition substrate such as an electronic device being processed. The paracyclophane precursor including a cross-linkable substituent such as an alkynyl is cracked at the phenyl linkages. The substrate is subjected to the*cracked precursor. As a result, an organic polymer is formed on the substrate. Cross-linking of the polymer through reaction, e.g. thermally induced reaction, of the cross-linkable substituents produces a thermally stable cross-linked polymer. The deposition of such cross-linked polymer is particularly useful for sealing ultra low k dielectric materials used in the damascene process in the production of integrated circuits. Alternatively the polymer is also advantageous as an adhesive in wafer-to-wafer bonding. Alternatively, the polymer is useful as a hardmask to replace silicon nitride and silicon carbide in the back-end-of-the-line processing of electronic devices.

Description

[0001] cross reference [0002] This application claims U.S. Provisional Patent Application 60 / 662,977, filed March 18, 2005, U.S. Provisional Patent Application 60 / 665,922, filed March 28, 2005, filed August 19, 2005, and September 21, 2005 Priority to U.S. Provisional Patent Application 60 / 709,844 filed on , all of which is claimed by John J. Senkevich, all of which are hereby incorporated by reference in their entirety. [0003] Federally Sponsored Research / Development Programs [0004] This invention was made with United States Government support under contract DASG60-01-C-0047 awarded by the United States Army Space and Missile Defense Command. The US Government has certain rights in this invention. technical field [0005] The present invention relates to chemical vapor deposition, and more particularly to chemical vapor deposition using organic precursors. Background technique [0006] Chemical vapor deposition (CVD) is a process used to form regions of material...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C23C16/00
Inventor J·J·森科维奇
Owner BREWER SCI
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