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Treichel, H. Ruhl, G. Ansmann, P. Würl, R. Müller, Ch. and Dietlmeier, M. 1998. Low dielectric constant materials for interlayer dielectric. Microelectronic Engineering, Vol. 40, Issue. 1, p. 1.
Homma, Tetsuya 1998. Low dielectric constant materials and methods for interlayer dielectric films in ultralarge-scale integrated circuit multilevel interconnections. Materials Science and Engineering: R: Reports, Vol. 23, Issue. 6, p. 243.
Hsu, D.T. Shi, F.G. Lopatin, S. Shacham-Diamand, Y. Zhao, B. Brongo, M. and Vasudev, P.K. 1999. Electroless copper deposition solution induced chemical changes in low-k fluorinated dielectrics. Materials Science in Semiconductor Processing, Vol. 2, Issue. 1, p. 19.
Agraharam, Sairam Hess, Dennis W. Kohl, Paul A. and Bidstrup Allen, Sue A. 1999. Plasma chemistry in fluorocarbon film deposition from pentafluoroethane/argon mixtures. Journal of Vacuum Science & Technology A: Vacuum, Surfaces, and Films, Vol. 17, Issue. 6, p. 3265.
Xu, Yuhuan Tsai, Yi-pin Tu, K. N. Zhao, Bin Liu, Q.-Z. Brongo, Maureen Sheng, George T. T. and Tung, C. H. 1999. Dielectric property and microstructure of a porous polymer material with ultralow dielectric constant. Applied Physics Letters, Vol. 75, Issue. 6, p. 853.
Morgen, Michael Ryan, E. Todd Zhao, Jie-Hua Hu, Chuan Cho, Taiheui and Ho, Paul S. 2000. Low Dielectric Constant Materials for ULSI Interconnects. Annual Review of Materials Science, Vol. 30, Issue. 1, p. 645.
Kwon, Y. Lu, J.-Q. Kraft, R. P. McDonald, J. F. Gutmann, R.J. and Cale, T. S. 2001. Wafer Bonding Using Dielectric Polymer Thin Films in 3D Integration. MRS Proceedings, Vol. 710, Issue. ,
Maier, G 2001. Low dielectric constant polymers for microelectronics. Progress in Polymer Science, Vol. 26, Issue. 1, p. 3.
Chiu, Patrick G. Hsu, David T. Kim, Hyung-Kun Shi, Frank G. Nalwa, Hari Singh and Zhao, Bin 2001. Handbook of Advanced Electronic and Photonic Materials and Devices. p. 201.
Xu, Yuhuan Zheng, D. W. Tsai, Yipin Tu, K. N. Zhao, Bin Liu, Q. Z. Brongo, Maureen Ong, Chung Wo Choy, Chung Loong Sheng, George T. T. and Tung, C. H. 2001. Synthesis and characterization of porous polymeric low dielectric constant films. Journal of Electronic Materials, Vol. 30, Issue. 4, p. 309.
Treichel, H. 2001. Low dielectric constant materials. Journal of Electronic Materials, Vol. 30, Issue. 4, p. 290.
Borst, Christopher L. Gill, William N. and Gutmann, Ronald J. 2002. Chemical-Mechanical Polishing of Low Dielectric Constant Polymers and Organosilicate Glasses. p. 17.
Ding, Jianfu Liu, Futian Li, Mei Day, Michael and Zhou, Ming 2002. Fluorinated poly(arylene ether ketone)s bearing pentafluorostyrene moieties prepared by a modified polycondensation. Journal of Polymer Science Part A: Polymer Chemistry, Vol. 40, Issue. 23, p. 4205.
Zhou, Ming 2002. Low-loss polymeric materials for passive waveguide components in fiber optical telecommunication. Optical Engineering, Vol. 41, Issue. 7, p. 1631.
Borst, Christopher L. Gill, William N. and Gutmann, Ronald J. 2002. Chemical-Mechanical Polishing of Low Dielectric Constant Polymers and Organosilicate Glasses. p. 1.
Maier, G. 2004. The search for low-/spl epsiv/ and ultra-low-/spl epsiv/ dielectrics: how far can you get with polymers? Part 2: materials, structures, properties. IEEE Electrical Insulation Magazine, Vol. 20, Issue. 3, p. 6.
Lu, Zhaoqiang Cheng, Lin Li, Jun Zhang, Kai Yi, Song and Qin, Jingui 2004. Synthesis and structural characterization of novel, fluorinated poly(phthalazinone ether)s containing perfluorophenylene moieties. Journal of Polymer Science Part A: Polymer Chemistry, Vol. 42, Issue. 4, p. 925.
Li, Xiuhua and Hay, Allan S. 2007. Synthesis of High Molecular Weight Fluorinated Poly(phthalazinone ether)s by Self‐Condensation of an AB‐Type Monomer and by Condensation of AA Monomers with Decafluorobiphenyl. Journal of Macromolecular Science, Part A, Vol. 44, Issue. 3, p. 249.
Kohl, Paul A. 2011. Low–Dielectric Constant Insulators for Future Integrated Circuits and Packages. Annual Review of Chemical and Biomolecular Engineering, Vol. 2, Issue. 1, p. 379.
Li, Xiuhua Gao, Yan Long, Qiang and Hay, Allan S. 2014. Synthesis and characterization of highly fluorinated poly(phthalazinone ether)s based on AB-type monomers. Journal of Polymer Science Part A: Polymer Chemistry, Vol. 52, Issue. 12, p. 1761.
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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. . 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.
Hide All (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. 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. (a) Oh, S.-Y., et al., “Interconnect Design”, SRC Topical Research Conference Workshop on Low Dielectric Constant Interlayer Dielectrics for High Performance Circuits, Rensselaer Polytechnic Institute, Troy, NY, Aug. 9–10, 1994; (b) T.S. Kuan, “Low Dielectric Constant Interlevel Dielectrics for High Performance Interconnects”, presented at the Dielectrics and CVD Metallization Symposium (sponsored by J.C. Schumacher Inc.), San Diego, CA, February 7–8, 1994. 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. Personal communication, Professor Murarka, S. P., Rensselaer Polytechnic Institute, August, 1993. (a) Geffken, R., IEDM Tech. Digest, 542, (1983); (b) R. Geffken, Electrochem. Soc. Extend. Abs., 364, 550 (1991).. Personal communication, Hummel, John (IBM), August, 1994. Saiki, A., et al., J. Electrochem. Soc., 124, 1619 (1977). Wilson, A. M., Thin Solid Films, 1, 145 (1981). (a) Luther, B., et al., Proceedings, 10th International VLSI Multilevel Interconnection Conference (VMIC), Santa Clara, CA, June 8–9, 1993, p. 15; (b) S. Bothra, et al., Proceedings, 10th International VLSI Multilevel Interconnection Conference (VMIC), Santa Clara, CA, June 8–9, 1993, p. 131; (c) X. Zhang, et al., Proceedings, 10th International VLSI Multilevel Interconnection Conference (VMIC), Santa Clara, CA, June 8–9, 1993., p. 168; (d) X. Zhang, et al., Proceedings, 11th International VLSI Multilevel Interconnection Conference (VMIC), Santa Clara, CA, June 7–8, 1994, p. 87; (e) X. Zhang, et al., SRC Topical Research Conference Workshop on Low Dielectric Constant Interlayer Dielectrics for High Performance Circuits, Rensselaer Polytechnic Institute, Troy, NY, August 9–10, 1994. 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. Ahlburn, B. J., et al, Proceedings, First International Dielectrics for VLSI/ULSI Multilevel Interconnection Conference, Santa Clara, CA, February 20–22,1995. Chen, L.-J., et al., Proceedings, 1 1th International VLSI Multilevel Interconnection Conference, Santa Clara, CA, June 7-8, 1994, p. 81. Drage, J. S., et al., Proceedings, 10th International VLSI Multilevel Interconnection Conference (VMIC), Santa Clara, CA, June 8-9, 1993, p. 128. Mercer, F. W. and Sovich, R., U.S. Patent Nos. 5,114,780 and 5,115,082 (assigned to AlliedSignal). 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. 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. Samples of ST-20 photoresist stripper were kindly provided by Sylvia Paul, ACSI Inc., (Milpitas, CA), 1994. 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. These data are courtesy of Drs. Chuanbin Pan and Chien Chiang, Intel Corporation, Santa Clara, CA, 1995. 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. Courtesy of Dr. Carlye Case, AT&T Bell Lab, 1995. Unpublished results of the University of Texas at Austin and Sematech, through the courtesy of Dr. Jim Leu, 1995. 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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