Design, synthesis, and characterization of novel, low dielectric, photodefinable polymers

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Please use this identifier to cite or link to this item: http://hdl.handle.net/1853/24782

Title: Design, synthesis, and characterization of novel, low dielectric, photodefinable polymers
Author: Romeo, Michael Joseph
Abstract: Polymers play an integral part in the semiconductor electronic industry. Due to the expanding diversity of a polymer s structural design and the resulting properties, different polymers serve as different components in the makeup and fabrication of the electronic package. The limiting factor in computer processing speed shifts from the transistors gate delay to the interconnect delay below a circuit line width of 1.8 μm for interlayer dielectrics. Silicon dioxide has been used as the insulating layer between metal lines for many computer chip generations. Low dielectric constant polymers will need to supplant silicon dioxide as interlayer dielectrics in order to develop reliable circuits for future generations. Along with serving as interlayer dielectrics, low dielectric constant polymers are also incorporated in first and second level electronic packaging. Deposition and patterning of these polymers can be significantly reduced by using photodefinable polymers. Most photodefinable polymers are in a precursor form for exposure and development in order to dissolve in industrial developers. Once developed, the polymer precursors are cured to produce the final polymer structure. This temperature is as high as 350 oC for many polymers. Thermal curing sets limitations on the use of the polymer in the electronics industry because of either the unwanted stress produced or the incompatibility of other electronic components that do not survive the thermal cure. In addition to a low dielectric constant and photodefinability, many other properties are needed for successful implementation. Polymers must be soluble in organic solvents in order to spin coat films. Water absorption increases the dielectric constant of the patterned films and can lead to various adhesion problems and cause delamination of the film. Mismatches between the coefficients of thermal expansion in adjacent layers can produce residual film stresses which leads to warping of the substrate or interfacial delamination. The glass transition temperature must be high because the thermal expansion is greatly increased when the glass transition temperature is exceeded. A high Young s modulus is also required to withstand external forces from thermal, electrical, and packaging stresses. The goal of this research was to develop novel, low dielectric, photodefinable polymers that can be processed at low temperatures. All polymers discussed will contain one of two monomers with hexafluoroalcohol (HFA) functional groups. Fluorine provides many properties that are advantageous for low dielectric applications whereas alcohols absorb water and increase the dielectric constant. Characterization of the polymers show the effect the fluorine has on the alcohol s high water absorption. All polymers will be synthesized by condensation polymerization of a diamine with a dianhydride or diacid chloride. All other polymers will contain a novel HFA diamine. A new thermoplastic polymer structure based on the cyclization of an HFA situated ortho to an amide linkage produces a benzoxazine ring in the polymer backbone. Cyclization to form polybenzoxazines occurs at temperatures considerably lower than that needed to form polyimides. The lowest processing temperatures are achieved with protection of the HFA that can be cleaved with a photoacid generator.
Type: Dissertation
URI: http://hdl.handle.net/1853/24782
Date: 2008-07-08
Publisher: Georgia Institute of Technology
Subject: Polybenzoxazine
Photosensitive
Microelectronics
Polyimide
Hexafluoroalcohol
Polyamide
Microelectronic packaging
Polymeric composites
Dielectrics
Photopolymerization
Photopolymers
Photosensitive polyimides
Department: Chemical Engineering
Advisor: Committee Chair: Henderson, Cliff; Committee Member: Beckham, Haskell; Committee Member: Hess, Dennis; Committee Member: Koros, William; Committee Member: Tolbert, Laren
Degree: Ph.D.

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