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Synthesis And Characterization Of Fluorinated Poly(Arylethers): Organic Polymers For Ic Imd

  • Neil H. Hendricks (a1), Kreisler S. Y. Lau (a1), Aaron R. Smith (a1) and W. Brad Wan (a1)

Abstract

Among the more promising approaches to minimizing capacitance in the multilevel interconnect of integrated circuits containing sub-half micron metal spacings is the development of organic polymers which exhibit high performance in key attributes such as thermal stability, low dielectric constant, and low moisture absorption coupled with high outgassing rates of what little moisture may be present. The use of such polymers as the intermetal dielectric can reduce power consumption and cross talk, while increasing signal propagation speed. While polyimides are the most extensively characterized polymer thin film dielectrics, and are in many cases suitable for the intermetal dielectrics in multichip modules, their tendency to absorb significant quantities of moisture, coupled with relatively slow outgas characteristics (presumably due to hydrogen bonding between water molecules and the carbonyls of the polyimide) constitute significant impediments to throughput in the fabrication of IC interconnects.

The search for alternative polymers which incorporate the “good” characteristics of polyimides while exhibiting improvements in electrical, moisture, and processing characteristics led us to the development of nominally 1 μm spin-on films derived from a family of noncarbonyl containing aromatic polyethers. Fluorinated poly(arylethers) based on decafluorobiphenyl exhibit thermal stability comparable to polyimides, from ten to forty times lower moisture absorption, dielectric constants in the mid-two's, and good retention of storage modulus above their glass transition temperatures. The precursor spin-on solutions, formulated in low toxicity organic solvents, exhibit excellent shelf life, and can be prepared with extremely low levels of metallic contamination. This paper describes the synthesis and both solution and film properties of this newly developed class of highly processible thermally stable polymers, first reported by Mercer, et. al. [1]. The characteristics of the polymers when spin-coated on silicon wafers is emphasized. Thermal and thermomechanical properties of nominally 10-25 μm free standing films are also described.

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[1] (a) Mercer, F.W. and Goodman, T.D., Proceedings, 1990 International Electronics Packaging Conference, Orlando, FL, September 10–12, 1990, p. 1042; (b) F.W. Mercer and T.D. Goodman, Polymer Preprints, 32 (21) 188 (1991); (c) N. Hendricks, Planar “94 Symposium (sponsored by AlliedSignal Advanced Microelectronic Materials), Sunnyvale, CA., June 6, 1994.
[2] This topic has received comprehensive coverage since 1984 in the annual Multilevel VLSI Interconnection Conferences (VMIC). The Conference Proceedings have been published by the IEEE through 1994.
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[4] The dielectric constant of many materials varies significantly with the frequency of measurement; for purposes of this paper, unless otherwise stated, dielectric constants refer to measurements at 1 MHz.
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[11] Ting, C. (Intel/Sematech), presented at SRC Topical Research Conference Workshop on Low Dielectric Constant Interlayer Dielectrics for High Performance Circuits, Rensselaer Polytechnic Institute, Troy, NY, August 9–10, 1994.
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[16] Hendricks, N. H., presented at the SRC Conference on Low Dielectric Constant Interlayer Dielectrics for High Performance Circuits, Rensselaer Polytechnic Institute, Troy, NY, August 9-10, 1994.
[17] Hendricks, N. H., Wan, W. B., and Smith, A. R., ”Fluorinated Poly(arylethers): Low Dielectric Constant, Thermally-Stable Polymers For Sub-Half Micron IMD Applications,” presented at the First International VMIC Specialty Conference on Dielectrics, Santa Clara, CA, February 20-22, 1995.
[18] Samples of ST-20 photoresist stripper were kindly provided by Sylvia Paul, ACSI Inc., (Milpitas, CA), 1994.
[19] Lau, K. S. Y., Hendricks, N. H., Smith, A. R., and Wan, W. B., ”Fluorinated Poly(aryl Ethers) As Organic Polymer Dielectrics For IC-IMD Applications: Synthesis, Characterization, Rheology, and Cure Behavior,” to be submitted to Twelfth International VLSI Multilevel Interconnection (VMIC) Conference & Poster Session, Santa Clara, CA, June 27-28, 1995.
[20] These data are courtesy of Drs. Chuanbin Pan and Chien Chiang, Intel Corporation, Santa Clara, CA, 1995.
[21] Lau, K. S. Y., Hendricks, N. H., Smith, A. R., and Wan, W. B., ”FLARETM, An Organic Polymer Dielectric For IC-IMD Applications: Chemistry, Characterization, Rheology, and Cure Behavior, to be submitted to the 48th Symposium on Semiconductors and Integrated Circuits Technology, Kikai-Shinkoh Kaikan, Tokyo, June 1–2, 1995.
[22] Courtesy of Dr. Carlye Case, AT&T Bell Lab, 1995.
[23] Unpublished results of the University of Texas at Austin and Sematech, through the courtesy of Dr. Jim Leu, 1995.
[24] Irvin, J. A., Neff, C. J., Kane, K. M., Cassidy, P. E., Tullos, G., and Clair, A. K. St., J. Polym. Sci.: Part A: Polym. Chem., 30, 1675, (1992).

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