Novel adamantane-based periodic mesoporous organosilica film with ultralow dielectric constant and high mechanical strength
Source abstract
Abstract
In this work, a novel bridged organosilane precursor, adamantane-bridged organosilane (ADBO), was synthesized successfully which was employed to prepare adamantane-based (ADH-based) periodic mesoporous organosilica (PMO) thin film in the presence of porogen and acid catalyst via evaporation-induced self-assembly (EISA) after spin-coating procedure. The resultant ADH-based PMO thin films were characterized by FTIR, NMR, TEM, and small-angle XRD. The ADH-based PMO thin film with weight ratio of porogen to ADBO (0.75:1) possesses low dielectric constant (1.55 ± 0.04@1 MHz), excellent Young’s modulus (6.69 ± 0.54 GPa), and ideal hydrophobic property (90.2° of water contact angle) simultaneously. These outstanding properties of ADH-based PMO film can be ascribed to lower polarity, lower density, and rigid cavity structure of adamantane, which suggests its potential application as high-performance low-κ material in next-generation microelectronics.
Source: openaire · Quality: candidate unverified · Source record ↗
Research context
OpenAlex topics: Silicone and Siloxane Chemistry · Mesoporous Materials and Catalysis · Copper Interconnects and Reliability
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (34)
Show source-provided references
1. Kohl PA (2011) Low-dielectric constant insulators for future integrated circuits and packages. Annu Rev Chem Biomol 2:379–40110.1146/annurev-chembioeng-061010-114137 ↗
2. Baklanov MR, Maex K (2006) Porous low dielectric constant materials for microelectronics. Philos Trans R Soc A 364:201–21510.1098/rsta.2005.1679 ↗
3. Shamiryan D, Abell T, Iacopi F, Maex K (2004) Low-k dielectric materials. Mater Today 7:34–3910.1016/S1369-7021(04)00053-7 ↗
4. Hatton BD, Landskron K, Hunks WJ, Bennett MR, Shukaris D, Perovic DD, Ozin GA (2006) Materials chemistry for low-k materials. Mater Today 9:22–3110.1016/S1369-7021(06)71387-6 ↗
5. Maex K, Baklanov MR, Shamiryan D, lacopi F, Brongersma SH, Yanovitskaya ZS (2003) Low dielectric constant materials for microelectronics. J Appl Phys 93:8793–884110.1063/1.1567460 ↗
6. Wang WD, Lofgreen JE, Ozin GA (2010) Why PMO? Towards functionality and utility of periodic mesoporous organosilicas. Small 6:2634–264210.1002/smll.201000617 ↗
7. Wang WD, Grozea D, Kohli S, Perovic DD, Ozin GA (2011) Water repellent periodic mesoporous organosilicas. ACS Nano 5:1267–127510.1021/nn102929t ↗
8. Yang QH, Liu J, Zhang L, Li C (2009) Functionalized periodic mesoporous organosilicas for catalysis. J Mater Chem A 19:1945–195510.1039/b815012e ↗
9. Lin CX, Qiao SZ, Yu CZ, Ismadji S, Lu GQ (2009) Periodic mesoporous silica and organosilica with controlled morphologies as carriers for drug release. Micro Mesopor Mat 117:213–21910.1016/j.micromeso.2008.06.023 ↗
10. Wang XQ, Lu DN, Austin R, Agarwal A, Mueller LJ, Liu Z, Wu JZ, Feng PY (2007) Protein refolding assisted by periodic mesoporous organosilicas. Langmuir 23:5735–573910.1021/la063507h ↗
11. Rebbin V, Schmidt R, Fröba M (2006) Spherical particles of phenylene-bridged periodic mesoporous organosilica for high-performance liquid chromatography. Angew Chem Int Ed 45:5210–521410.1002/anie.200504568 ↗
12. Tani T, Mizoshita N, Inagaki S (2009) Luminescent periodic mesoporous organosilicas. J Mater Chem 19:4451–445610.1039/b820691k ↗
13. Hunks WJ, Ozin GA (2005) Challenges and advances in the chemistry of periodic mesoporous organosilicas (PMOs). J Mater Chem 15:3716–372410.1039/b504511h ↗
14. Wills AW, Michalak DJ, Ercius P, Rosenberg ER, Perciano T, Ushizima D, Runser R, Helms BA (2015) Block copolymer packing limits and interfacial reconfigurability in the assembly of periodic mesoporous organosilicas. Adv Funct Mater 25:4120–412810.1002/adfm.201501059 ↗
15. Hoffmann F, Cornelius M, Morell J, Fröba M (2006) Silica-based mesoporous organic–inorganic hybrid materials. Angew Chem Int Ed 45:3216–325110.1002/anie.200503075 ↗
16. Liu HC, Su WC, Liu YL (2011) Self-assembled benzoxazine-bridged polysilsesquioxanes exhibiting ultralow-dielectric constants and yellow-light photoluminescent emission. J Mater Chem 21:7182–718710.1039/c1jm10815h ↗
17. Hatton BD, Landskron K, Whitnall W, Perovic DD, Ozin GA (2005) Spin-coated periodic mesoporous organosilica thin film-towards a new generation of low-dielectric-constant materials. Adv Funct Mater 15:823–82910.1002/adfm.200400221 ↗
18. Jiang T, Zhu B, Ding SJ, Fan ZY, Zhang DW (2014) High-performance ultralow dielectric constant carbon-bridged mesoporous organosilica films for advanced interconnects. J Mater Chem C 2:6502–651010.1039/C4TC00901K ↗
19. Huang YQ, Economy J (2006) New high strength low-k spin-on thin films for IC application. Macromolecules 39:1850–185310.1021/ma0518398 ↗
20. Edelstein D (2008) Extendibility of Cu/low-k/airgap BEOL. Electrochem Soc 28:2073
21. Guo Y, Mylonakis A, Zhang ZT, Yang GL, Lelkes PI, Che SN, Lu QH, Wei Y (2008) Templated synthesis of electroactive periodic mesoporous organosilica bridged with oligoaniline. Chem-Eur J 14:2909–291710.1002/chem.200701605 ↗
22. Landskron K, Ozin GA (2005) Periodic mesoporous organosilicas: self-assembly from bridged cyclic silsesquioxane precursors. Angew Chem Int Ed 44:2107–210910.1002/anie.200462279 ↗
23. Gao L, Wei F, Zhou Y, Fan XX, Wang Y, Zhu JH (2009) Periodic mesoporous organosilica materials: self-assembly of carbamothioic acid-bridged organosilane precursors. Chem-Eur J 15:8310–831810.1002/chem.200900352 ↗
24. Schachtschneider A, Wessig M, Spitzbarth M, Donner A, Fischer C, Drescher M, Polarz S (2015) Directional materials-nanoporous organosilica monoliths with multiple gradients prepared using click chemistry. Angew Chem Int Ed 127:10611–1061510.1002/ange.201502878 ↗
25. Seino M, Wang WD, Lofgreen JE, Puzzo DP, Manabe T, Ozin GA (2011) Low-k periodic mesoporous organosilica with air walls: POSS-PMO. J Am Chem Soc 133:18082–1808510.1021/ja2080136 ↗
26. Lu HY, Teng CL, Kung CH, Wan BZ (2011) Preparing mesoporous low-k films with high mechanical strength from noncrystalline silica particles. Ind Eng Chem Res 50:3265–327310.1021/ie1018436 ↗
27. Goethals F, Levrau E, Pollefeyt G, Baklanov MR, Ciofi I, Vanstreels K, Detavernier C, Driessche IV, PVD Voort (2013) Sealed ultra low-k organosilica films with improved electrical, mechanical and chemical properties. J Mater Chem C1:3961–3966
28. Yuan H, Xu JQ, Xie LL (2011) Ultra low-dielectric-constant methylated mesoporous silica films with high hydrophobicity and stability. Mater Chem Phys 129:1195–120010.1016/j.matchemphys.2011.06.006 ↗
29. Rathore JS, Interrante LV, Dubois G (2008) Ultra low-k films derived from hyperbranched polycarbosilanes (HBPCS). Adv Funct Mater 18:4022–402810.1002/adfm.200801197 ↗
30. Zhang JW, Zhang GP, Gao YJ, Sun R, Wong CP (2016) Ultra-low-κ HFPDB-based periodic mesoporous organosilica film with high mechanical strength for interlayer dielectric. J Mater Sci 51:7966–797610.1007/s10853-016-0066-6 ↗
31. Zhang GP, George TF, Assoufid L, Mansoori GA (2007) First-principles simulation of the interaction between adamantane and an atomic-force-microscope tip. Phys Rev B 75:03541310.1103/PhysRevB.75.035413 ↗
32. Fort RC, Schleyer PV (1964) Adamantane: consequences of the diamondoid structure. Chem Rev 64:277–30010.1021/cr60229a004 ↗
33. Tong J, Zhang H, Gu J, Li L, Ma C, Zhao J, Wang C (2016) Poly (ethylene glycol)-block-poly (propylene glycol)-block-poly (ethylene glycol)-assisted synthesis of graphene/polyaniline composites as high-performance supercapacitor electrodes. J Mater Sci 51:1966–197710.1007/s10853-015-9506-y ↗
34. Landskron K, Hatton BD, Perovic DD, Ozin GA (2003) Periodic mesoporous organosilicas containing interconnected [Si(CH2)]3 rings. Science 302:266–26910.1126/science.1084973 ↗