Development of a Low-Dielectric-Constant Polymer for the Fabrication of Integrated Circuit Interconnect

Martin, Steven J.; Godschalx, J. P.; Mills, M. E.; Shaffer, Edward O.; Townsend, P. H.

doi:10.1002/1521-4095(200012)12:23<1769::aid-adma1769>3.0.co;2-5

Cited by 337 publications

(236 citation statements)

References 7 publications

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“…For many applications of the integrated material structures, wrinkling is undesirable as it may lead to failure by delamination or fracture (e.g., Suo, 1995;Martin et al, 2000;Mumm et al, 2001;Yin et al, 2003;Peterson, 2006). On the other hand, wrinkling has also been exploited as an enabling mechanism for a variety of applications, such as stretchable electronics (Watanabe et al, 2002;Lacour et al, 2003;Choi et al, 2007), micro/nanoscale surface patterning (Huck et al, 2000;Serrano and Cahill, 2002;Ohzono and Shimomura, 2004;Chan and Crosby, 2006), optical phase grating , microfluidic sieves (Efimenko et al, 2005), smart adhesion (Chan et al, 2008), and metrology aid for measuring mechanical properties of thin films .…”

Section: Introductionmentioning

confidence: 99%

Wrinkle patterns of anisotropic crystal films on viscoelastic substrates

Huang

2008

Journal of the Mechanics and Physics of Solids

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This paper presents a nonlinear mathematical model for evolution of wrinkle patterns of an anisotropic crystal film on a viscoelastic substrate layer. The underlying mechanism of wrinkling has been generally understood as a stress-driven instability. Previously, theoretical studies on wrinkling have assumed isotropic elastic properties for the film. Motivated by recent experimental observations of ordered wrinkle patterns in single-crystal thin films, this paper develops a theoretical model coupling anisotropic elastic deformation of a crystal film with viscoelastic deformation of a thin substrate layer. A linear perturbation analysis is performed to predict onset of the wrinkling instability and the initial evolution kinetics; an energy minimization method is adopted to analyze wrinkle patterns at the equilibrium states. For a cubic crystal film under an equi-biaxial compression, orthogonally ordered wrinkle patterns are predicted at both the initial stage and the equilibrium state. This is confirmed by numerical simulations of evolving wrinkle patterns. By varying the residual stresses in the film, numerical simulations show that a variety of wrinkle patterns (e.g., orthogonal, parallel, zigzag, and checkerboard patterns) emerge as a result of the competition between the material anisotropy and the stress anisotropy.

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Section: Introductionmentioning

confidence: 99%

Wrinkle patterns of anisotropic crystal films on viscoelastic substrates

Huang

2008

Journal of the Mechanics and Physics of Solids

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“…Phenylethynyl-substituted aromatic systems for preparation of thermostable resins in which the phenylethynyl groups are oriented ortho to each other have lower temperatures for the onset of polymerization, and thus the hazards of handling are reduced (26). Replacement of the phenyl group with a pyridine should enhance the reactivity of the carbon-carbon triple bond in polymerization reactions.…”

Section: Vol 69 2003 Production Of 6-phenylacetylene Picolinic Acidmentioning

confidence: 99%

“…The goal of the work described here was to synthesize a more complex molecule, 6-phenylacetylene picolinic acid [6-(2-phenylethynyl)pyridine-2-carboxylic acid]. The potential reactivity of 6-phenylacetylene picolinate as a cross-linker or a dienophile makes it a good candidate to replace phenylacetylenes as endcapping agents for high-performance thermosetting polymers for aerospace applications (17) and electronic packaging (26). The strong electron-withdrawing properties of the pyridine moiety are predicted to allow lower reaction temperatures and shorter cure times during Diels-Alder-type polymerization.…”

mentioning

confidence: 99%

Production of 6-Phenylacetylene Picolinic Acid from Diphenylacetylene by a Toluene-Degrading Acinetobacter Strain

Spain¹,

Nishino²,

Tan

et al. 2003

Appl Environ Microbiol

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Several strategies for using enzymes to catalyze reactions leading to the synthesis of relatively simple substituted picolinic acids have been described. The goal of the work described here was to synthesize a more complex molecule, 6-phenylacetylene picolinic acid [6-(2-phenylethynyl)pyridine-2-carboxylic acid], for use as a potential endcapping agent for aerospace polymers. We screened 139 toluene-degrading strains that use a variety of catabolic pathways for the ability to catalyze oxidative transformation of diphenylacetylene. Acinetobacter sp. strain F4 catalyzed the overall conversion of diphenylacetylene to a yellow metabolite, which was identified as a putative meta ring fission product (2-hydroxy-8-phenyl-6-oxoocta-2,4-dien-7-ynoic acid [RFP]). The activity could be sustained by addition of toluene at a flow rate determined empirically so that the transformations were sustained in spite of the fact that toluene is a competitive inhibitor of the enzymes. The overall rate of transformation was limited by the instability of RFP. The RFP was chemically converted to 6-phenylacetylene picolinic acid by treatment with ammonium hydroxide. The results show the potential for using the normal growth substrate to provide energy and to maintain induction of the enzymes involved in biotransformation during preliminary stages of biocatalyst development.Substituted picolinic acids are used as feedstocks for the synthesis of a variety of pharmaceuticals, agricultural chemicals, and dyes (1, 12). Chemical synthesis involves several steps and the use of harsh reagents, and low yields of the desired products are obtained. Several strategies for using enzymes to catalyze reactions leading to the synthesis of picolinic acid have been described. The first reports (3, 29) described production of 2-hydroxymuconic semialdehyde from catechol catalyzed by dioxygenase enzymes from two strains of gram-negative bacteria. Treatment of the 2-hydroxymuconic semialdehyde with ammonium ions led to the formation of picolinic acid. This reaction has been the basis for a number of subsequent papers (1) and patents (11,12) describing the synthesis of substituted picolinic acids. Recently, a related strategy involving cleavage of the ring of substituted 2-aminophenols by aminophenol dioxygenase from Pseudomonas pseudoalcaligenes strain JS 45 was described (16). The resultant ring fission product rearranges spontaneously to the corresponding picolinic acid. The techniques described above have been used for synthesis of relatively simple substituted picolinic acids. The goal of the work described here was to synthesize a more complex molecule, 6-phenylacetylene picolinic acid [6-(2-phenylethynyl)pyridine-2-carboxylic acid]. The potential reactivity of 6-phenylacetylene picolinate as a cross-linker or a dienophile makes it a good candidate to replace phenylacetylenes as endcapping agents for high-performance thermosetting polymers for aerospace applications (17) and electronic packaging (26). The strong electron-withdrawing properties of the pyri...

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“…This fact is brought to attention recently in the development of low dielectric constant polymers for interconnect structures [41]. These authors coat a silicon wafer with a polymer layer, and then deposit a SiN thin film on the polymer, with the SiN film under a compressive residual stress.…”

Section: Equilibrium Wrinklesmentioning

confidence: 99%

Mechanics of relaxing SiGe islands on a viscous glass

et al. 2002

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A process has been developed recently to fabricate a structure comprising, from top to bottom, a SiGe thin film, a glass layer, and a Si wafer. The SiGe film is a perfect crystal, and is under biaxial compression. The SiGe film is patterned into islands. On annealing, the glass flows and the islands relax. The resulting strain-free islands are used as substrates, to grow epitaxial optoelectronic devices. This article describes a series of studies on the anneMing process, combining experiment and theory. A small island relaxes by expansion, starting at the edges and diffusing to the center. A large island wrinkles before the expansion reaches the center. After some time, the wrinkles either disappear, or cause the island to fracture. We model the island as an elastic plate, and the glass layer as a viscous liquid. The strains in the islands are measured by X-ray diffraction and Raman spectroscopy, and the wrinkle amplitudes by atomic force microscope. The data are compared with the theoretical predictions. We determine the conditions under which the islands relax by expansion without significant wrinkling, and demonstrate that a cap layer suppresses wrinkles, relaxing a large island crack-free.

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Development of a Low-Dielectric-Constant Polymer for the Fabrication of Integrated Circuit Interconnect

Cited by 337 publications

References 7 publications

Wrinkle patterns of anisotropic crystal films on viscoelastic substrates

Wrinkle patterns of anisotropic crystal films on viscoelastic substrates

Production of 6-Phenylacetylene Picolinic Acid from Diphenylacetylene by a Toluene-Degrading Acinetobacter Strain

Mechanics of relaxing SiGe islands on a viscous glass

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