

FOLLOWUS
School of Materials and Energy, University of Electronic Science and Technology of China, Chengdu 610054, China
tonglifen0214@163.com (L.F.T.)
liuxb@uestc.edu.cn (X.B.L.)
Received:10 February 2020,
Revised:2020-2-28,
Accepted:04 March 2020,
Online First:18 May 2020,
Published:14 August 2020
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Lei, X. T.; Tong, L. F.; Xu, M. Z.; You, Y.; Liu, X. B. PEN/BADCy interlayer dielectric films with tunable microstructures , via, an assist of temperature for enhanced frequency stability. Chinese J. Polym. Sci. 2020, 38, 1258–1266
Xi-Ting Lei, Li-Fen Tong, Ming-Zhen Xu, et al. PEN/BADCy Interlayer Dielectric Films with Tunable Microstructures
Lei, X. T.; Tong, L. F.; Xu, M. Z.; You, Y.; Liu, X. B. PEN/BADCy interlayer dielectric films with tunable microstructures , via, an assist of temperature for enhanced frequency stability. Chinese J. Polym. Sci. 2020, 38, 1258–1266 DOI: 10.1007/s10118-020-2417-7.
Xi-Ting Lei, Li-Fen Tong, Ming-Zhen Xu, et al. PEN/BADCy Interlayer Dielectric Films with Tunable Microstructures
Low dielectric interlayer films have become an important element to ensure the development of the microelectronics industry. A kind of flexible interlayer dielectrics
polyarylene ether nitrile/bisphenol A cyanate ester (PEN/BADCy) film
with good thermal stability and low frequency dependence
has been developed by solution casting method. Herein
materials were designed to incorporate bisphenol A cyanate ester as a part of blend
contributing to the frequency stability and structural integrity. The morphological study combined with electron microscopy revealed the uniform and flexible microstructure information with controllable morphology through self-polymerization of cyanate esters with different prepolymerization time and curing temperatures. The dielectric films could present high thermal stability with
T
g
>
180 °C. Significant improvement in the dielectric properties was achieved for the dielectric constant and loss was much stabler than neat PEN over the frequency range from 100 Hz to 5 MHz. When the prepolymerization time was 3 h and final curing temperature reached 230 °C
the dielectric constant and dielectric loss of the films were 3.36 and 0.013 at 100 kHz
respectively. The dimensional stability (CTE = 53.67 × 10
−6
K
−1
) was confirmed and considered beneficial to use as an interlayer dielectrics.
Baklanov, M. R.; Adelmann, C.; Zhao, L.; Gendt, S. D. . Advanced interconnects: materials, processing, and reliability . ECS J. Solid State Sci. Technol. , 2014 . 4 Y1 - Y4 . DOI: 10.1149/2.0271501jss http://doi.org/10.1149/2.0271501jss .
Sunday, C. E.; Montgomery, K. R.; Amoah, P. K.; Obeng, Y. S. . Broadband dielectric spectroscopic characterization of thermal stability of low- k dielectric thin films for micro- and nanoelectronic applications . ECS J. Solid State Sci. Technol. , 2017 . 6 N155 - N162 . DOI: 10.1149/2.0141709jss http://doi.org/10.1149/2.0141709jss .
Tsujimura, M. . The way to zeros: the future of semiconductor device and chemical mechanical polishing technologies . Jpn. J. Appl. Phys. , 2016 . 55 6S3 DOI: 10.7567/JJAP.55.06JA01 http://doi.org/10.7567/JJAP.55.06JA01 .
Yuan, C.; Jin, K.; Li, K.; Diao, S.; Tong, J.; Fang, Q . Non-porous low- k dielectric films based on a new structural amorphous fluoropolymer . Adv. Mater. , 2013 . 25 4875 - 4878 . DOI: 10.1002/adma.201302021 http://doi.org/10.1002/adma.201302021 .
Aziz, S. B.; Kadir, M. F. Z.; Hamsan, M. H.; Woo, H. J.; Brza, M. A. . Development of polymer blends based on PVA: POZ with low dielectric constant for microelectronic applications . Sci. Rep. , 2019 . 9 13163 DOI: 10.1038/s41598-019-49715-8 http://doi.org/10.1038/s41598-019-49715-8 .
Ramani, C.; Ramachandran, R.; Amarendra, G.; Alam, S. . Direct correlation between free volume and dielectric constant in a fluorine-containing polyimide blend . J. Phys.: Conf. Ser. , 2015 . 618 012025 DOI: 10.1088/1742-6596/618/1/012025 http://doi.org/10.1088/1742-6596/618/1/012025 .
Volksen, W.; Miller, R. D.; Dubois, G. . Low dielectric constant materials . Chem. Rev. , 2010 . 110 56 - 110 . DOI: 10.1021/cr9002819 http://doi.org/10.1021/cr9002819 .
Ortiz, R. P.; Facchetti, A.; Marks, T. J. . High- k organic, inorganic, and hybrid dielectrics for low-voltage organic field-effect transistors . Chem. Rev. , 2010 . 110 205 - 239 . DOI: 10.1021/cr9001275 http://doi.org/10.1021/cr9001275 .
Qian, C.; Bei, R.; Zhu, T.; Zheng, W.; Liu, S.; Chi, Z.; Aldred, M. P.; Chen, X.; Zhang, Y.; Xu, J. . Facile strategy for intrinsic low- k dielectric polymers: molecular design based on secondary relaxation behavior . Macromolecules , 2019 . 52 4601 - 4609 . DOI: 10.1021/acs.macromol.9b00136 http://doi.org/10.1021/acs.macromol.9b00136 .
Chen, Z.; Pei, J.; Li, R. . Study of the preparation and dielectric property of PP/SMA/PVDF blend material . Appl. Sci. , 2017 . 7 389 DOI: 10.3390/app7040389 http://doi.org/10.3390/app7040389 .
Chen, L.; Li, K.; Li, B.; Ren, D.; Chen, S.; Xu, M.; Liu, X . Enhanced thermal conductivity of benzoxazine nanocomposites based on non-covalent functionalized hexagonal boron nitride . Compos. Sci. Technol. , 2019 . 182 107741 DOI: 10.1016/j.compscitech.2019.107741 http://doi.org/10.1016/j.compscitech.2019.107741 .
Tao, D.; Li, X.; Dong, Y.; Zhu, Y.; Yuan, Y.; Ni, Q.; Fu, Y.; Fu, S . Super-low thermal conductivity fibrous nanocomposite membrane of hollow silica/polyacrylonitrile . Compos. Sci. Technol. , 2020 . 188 107992 DOI: 10.1016/j.compscitech.2020.107992 http://doi.org/10.1016/j.compscitech.2020.107992 .
Zhang, Y.; Shen, Y.; Shi, K.; Wang, T.; Eileen, H. J. . Constructing a filler network for thermal conductivity enhancement in epoxy composites via reaction-induced phase separation . Compos. Part A , 2018 . 110 62 - 69 . DOI: 10.1016/j.compositesa.2018.04.009 http://doi.org/10.1016/j.compositesa.2018.04.009 .
Kim, S. Y.; Lim, T. W.; Sottos, N. R.; White, S. R. . Manufacture of carbon-fiber prepreg with thermoplastic/epoxy resin blends and microencapsulated solvent healing agents . Compos. Part A , 2019 . 121 365 - 375 . DOI: 10.1016/j.compositesa.2019.03.033 http://doi.org/10.1016/j.compositesa.2019.03.033 .
You, Y.; Liu, S.; Tu, L.; Wang, Y.; Zhan, C.; Du, X.; Wei, R.; Liu, X. . Controllable fabrication of poly(arylene ether nitrile) dielectrics for thermal-resistant film capacitors . Macromolecules , 2019 . 52 5850 - 5859 . DOI: 10.1021/acs.macromol.9b00799 http://doi.org/10.1021/acs.macromol.9b00799 .
Wang, L.; Liu, X.; Liu, C.; Zhou, X.; Liu, C.; Cheng, M.; Wei, R.; Liu, X. . Ultralow dielectric constant polyarylene ether nitrile foam with excellent mechanical properties . Chem. Eng. J. , 2020 . 384 123231 DOI: 10.1016/j.cej.2019.123231 http://doi.org/10.1016/j.cej.2019.123231 .
Qi, Q.; Zheng, P.; Lei, Y.; Liu, X. . Design of bi-modal pore structure polyarylene ether nitrile/SiO 2 foams with ultralow- k dielectric and wave transparent properties by supercritical carbon dioxide . Compos. Part B , 2019 . 173 106915 DOI: 10.1016/j.compositesb.2019.106915 http://doi.org/10.1016/j.compositesb.2019.106915 .
Lei, X.; Tong, L.; Pan, H.; Yang, G.; Liu, X. . Preparation of polyarylene ether nitriles/fullerene composites with low dielectric constant by cosolvent evaporation . J. Mater. Sci.: Mater. Electron. , 2019 . 30 18297 - 18305 . DOI: 10.1007/s10854-019-02145-8 http://doi.org/10.1007/s10854-019-02145-8 .
Tong, L.; Lei, X.; Yang, G.; Liu, X. . Self-toughening and self-enhancement poly(arylene ether nitrile) with low dielectric constant by solid crosslinking reaction . Polymers , 2019 . 11 1403 DOI: 10.3390/polym11091403 http://doi.org/10.3390/polym11091403 .
Pu, Z.; Zheng, X.; Tian, Y.; Hu, L.; Zhong, J. . Flexible ultrahigh-temperature polymer-based dielectrics with high permittivity for film capacitor applications . Polymers , 2017 . 9 596 DOI: 10.3390/polym9110596 http://doi.org/10.3390/polym9110596 .
Guan, Q.; Yuan, L.; Zhang, Y.; Gu, A.; Liang, G. . Improving the mechanical, thermal, dielectric and flame retardancy properties of cyanate ester with the encapsulated epoxy resin-penetrated aligned carbon nanotube bundle . Compos. Part B , 2017 . 123 81 - 91 . DOI: 10.1016/j.compositesb.2017.05.029 http://doi.org/10.1016/j.compositesb.2017.05.029 .
Gu, J.; Dong, W.; Tang, Y.; Guo, Y.; Tang, L.; Kong, J.; Tadakamalla, S.; Wang, B.; Guo, Z. . Ultralow dielectric, fluoride-containing cyanate ester resins with improved mechanical properties and high thermal and dimensional stabilities . J. Mater. Chem. C , 2017 . 5 6929 - 6936 . DOI: 10.1039/C7TC00222J http://doi.org/10.1039/C7TC00222J .
Inamdar, A.; Cherukattu, J.; Anand, A.; Kandasubramanian, B. . Thermoplastic-toughened high-temperature cyanate esters and their application in advanced composites . Ind. Eng. Chem. Res. , 2018 . 57 4479 - 4504 . DOI: 10.1021/acs.iecr.7b05202 http://doi.org/10.1021/acs.iecr.7b05202 .
Gu. J.; Yang, X.; Li, C.; Kou, K. . Synthesis of cyanate ester microcapsules via solvent evaporation technique and its application in epoxy resins as a healing agent . Ind. Eng. Chem. Res. , 2016 . 55 10941 - 10946 . DOI: 10.1021/acs.iecr.6b03093 http://doi.org/10.1021/acs.iecr.6b03093 .
Wang, B.; Liu, L.; Liang, G.; Yuan, L.; Gu, A. . Boost up dielectric constant and push down dielectric loss of carbon nanotube/cyanate ester composites via gradient and layered structure design . J. Mater. Chem. A , 2015 . 3 23162 - 23169 . DOI: 10.1039/C5TA07611K http://doi.org/10.1039/C5TA07611K .
Fyfe, C. A.; Niu, J.; Rettig, S. J.; Burlinson, N. E. . High-resolution carbon-13 and nitrogen-15 NMR investigations of themechanism of the curing reactions of cyanate-based polymer resinsin solution and the solid state . Macromolecules , 1992 . 25 6289 - 6301 . DOI: 10.1021/ma00049a028 http://doi.org/10.1021/ma00049a028 .
Ma, J.; Lei, X.; Tian, D.; Yuan, L.; Liao, C. . Curing behavior and network formation of cyanate ester resin/polyethylene glycol . J. Appl. Polym. Sci. , 2015 . 132 41841 - 41852 . .
Simon, S. L.; Gillham, J. K. . Cure Kinetics of a thermosetting liquid dicyanate ester monomer/high- T g polycyanurate material . J. Appl. Polym. Sci. , 1993 . 47 461 - 485 . DOI: 10.1002/app.1993.070470308 http://doi.org/10.1002/app.1993.070470308 .
Harvey, B. G.; Guenthner, A. J.; Koontz, T. A.; Storch, P. J.; Reams, J. T.; Groshens, T. J. . Sustainable hydrophobic thermosetting resins and polycarbonates from turpentine . Green Chem. , 2016 . 18 2416 - 2423 . DOI: 10.1039/C5GC02893K http://doi.org/10.1039/C5GC02893K .
Wei, J.; Meng, X.; Chen, X.; Bai, Y.; Song, J.; Yan, N.; Zhu, L.; Shen, A. . Facile synthesis of fluorinated poly(arylene ether nitrile) and its dielectric properties . J. Appl. Polym. Sci. , 2018 . 135 46837 - 46844 . DOI: 10.1002/app.46837 http://doi.org/10.1002/app.46837 .
Hamerton, I.; Hay, J. N. . Recent technological developments in cyanate ester resins . High Perform. Polym. , 1998 . 10 163 - 174 . DOI: 10.1088/0954-0083/10/2/001 http://doi.org/10.1088/0954-0083/10/2/001 .
Zhan, G.; Hu, S.; Yu, Y.; Li, S.; Tang, X. . The study on poly(ether sulfone) modified cyanate ester resin and epoxy resin cocuring blends . J. Appl. Polym. Sci. , 2009 . 113 60 - 70 . DOI: 10.1002/app.29867 http://doi.org/10.1002/app.29867 .
Hwang, J. W.; Cho, K.; Yoon, T. H.; Park, C. E. . Effects of molecular weight of polysulfone on phase separation behavior for cyanate ester/polysulfone blends . J. Appl. Polym. Sci. , 2000 . 77 921 - 927 . DOI: 10.1002/(SICI)1097-4628(20000725)77:4<921::AID-APP28>3.0.CO;2-4 http://doi.org/10.1002/(SICI)1097-4628(20000725)77:4<921::AID-APP28>3.0.CO;2-4 .
Ding, Y.; Liu, R.; Liu, H. . Investigation on viscoelastic phase separation of phenolphthalein poly(ether ether ketone)/epoxy blends system . Polym. Polym. Compos. , 2020 . 28 199 - 208 . DOI: 10.1177/0967391119869111 http://doi.org/10.1177/0967391119869111 .
Tree, D. R.; Dos Santos, L. F.; Wilson, C. B.; Scott, T. R.; Garcia, J. U.; Fredrickson, G. H. . Mass-transfer driven spinodal decomposition in a ternary polymer solution . Soft Matter , 2019 . 15 4614 - 4628 . DOI: 10.1039/C9SM00355J http://doi.org/10.1039/C9SM00355J .
Hwang, J. W.; Cho, K.; Park, C. E.; Huh, W. . Phase separation behavior of cyanate ester resin/polysulfone blends . J. Appl. Polym. Sci. , 1999 . 74 33 - 45 . DOI: 10.1002/(SICI)1097-4628(19991003)74:1<33::AID-APP4>3.0.CO;2-Q http://doi.org/10.1002/(SICI)1097-4628(19991003)74:1<33::AID-APP4>3.0.CO;2-Q .
Kim, B. S.; Chiba, T.; Inoue, T. . Morphology development via reaction-induced phase separation In epoxy/poly(ether sulfone) blends: morphology control using poly(ether sulfone) with functional end-groups . Polymer , 1995 . 36 43 - 47 . DOI: 10.1016/0032-3861(95)90673-P http://doi.org/10.1016/0032-3861(95)90673-P .
Snow, A. W.; Griffith, J. R.; Marullo, N. P. . Syntheses and characterization of heteroatom-bridged metal-free phthalocyanine network polymers and model compounds . Macromolecules , 1984 . 17 1614 - 1624 . DOI: 10.1021/ma00138a033 http://doi.org/10.1021/ma00138a033 .
Chen, S.; Ren, D.; Li, B.; Li, K.; Chen, L.; Xu, M.; Liu, X. . Benzoxazine containing fluorinated aromatic ether nitrile linkage: preparation, curing kinetics and dielectric properties . Polymers , 2019 . 11 1036 DOI: 10.3390/polym11061036 http://doi.org/10.3390/polym11061036 .
Zeng, X.; Deng, L.; Yao, Y.; Sun, R.; Xu, J.; Wong, C. P. . Flexible dielectric papers based on biodegradable cellulose nanofibers and carbon nanotubes for dielectric energy storage . J. Mater. Chem. C , 2016 . 4 6037 - 6044 . DOI: 10.1039/C6TC01501H http://doi.org/10.1039/C6TC01501H .
Zeltmann, S. E.; Chen, B.; Gupta, N. . Thermal expansion and dynamic mechanical analysis of epoxy matrix-borosilicate glass hollow particle syntactic foams . J. Cell. Plast. , 2017 . 54 463 - 481 . .
Liang, T.; Qi, L.; Ma, Z.; Xiao, Z.; Wang, Y.; Liu, H.; Zhang, J.; Guo, Z.; Liu, C.; Xie, W.; Ding, T.; Lu, N. . Experimental study on thermal expansion coefficient of composite multi-layered flaky gun propellants . Compos. Part B , 2019 . 166 428 - 435 . DOI: 10.1016/j.compositesb.2019.02.024 http://doi.org/10.1016/j.compositesb.2019.02.024 .
Yoo, S.; Kandare, E.; Shanks, R.; Maadeed, M. A. A.; Khatibi, A. A. . Thermophysical properties of multifunctional glass fibre reinforced polymer composites incorporating phase change materials . Thermochim. Acta , 2016 . 642 25 - 31 . DOI: 10.1016/j.tca.2016.09.003 http://doi.org/10.1016/j.tca.2016.09.003 .
Hamerton, I.; Howlin, B. J.; Klewpatinond, P.; Takeda, S. . Examination of the thermal and thermomechanical behavior of novel cyanate ester homopolymers and blends with low coefficients of thermal expansion . Macromolecules , 2009 . 42 7718 - 7735 . DOI: 10.1021/ma901657n http://doi.org/10.1021/ma901657n .
Yao, Y.; Zeng, X.; Guo, K.; Sun, R.; Xu, J. B. . The effect of interfacial state on the thermal conductivity of functionalized Al 2 O 3 filled glass fibers reinforced polymer composites . Compos. Part A , 2015 . 69 49 - 55 . DOI: 10.1016/j.compositesa.2014.10.027 http://doi.org/10.1016/j.compositesa.2014.10.027 .
Wong C. P.; Bollampally R. S. . Thermal conductivity, elastic modulus, and coefficient of thermal expansion of polymer composites filled with ceramic particles for electronic packaging . J. Appl. Polym. Sci. , 1999 . 74 3396 - 3403 . DOI: 10.1002/(SICI)1097-4628(19991227)74:14<3396::AID-APP13>3.0.CO;2-3 http://doi.org/10.1002/(SICI)1097-4628(19991227)74:14<3396::AID-APP13>3.0.CO;2-3 .
Wooster T. J.; Abrol S.; Hey J. M.; MacFarlane D. R. . Thermal, mechanical, and conductivity properties of cyanate ester composites . Compos. Part A , 2004 . 35 75 - 82 . .
Gu A.; Chang F. C. . A novel preparation of polyimide/clay hybrid films with low coefficient of thermal expansion . J. Appl. Polym. Sci. , 2000 . 79 289 - 294 . DOI: 10.1002/1097-4628(20010110)79:2<289::AID-APP100>3.3.CO;2-M http://doi.org/10.1002/1097-4628(20010110)79:2<289::AID-APP100>3.3.CO;2-M .
Goyal R. K.; Jadhav P.; Tiwari A. N. . Preparation and properties of new polyphenylene sulfide/AlN composites for electronic packaging . J. Electron. Mater. , 2011 . 40 1377 - 1383 . DOI: 10.1007/s11664-011-1520-5 http://doi.org/10.1007/s11664-011-1520-5 .
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