1.大连理工大学高分子材料系 大连 116024
2.航天材料及工艺研究所 北京 100076
E-mail: jian4616@dlut.edu.cn
收稿:2026-01-27,
录用:2026-03-19,
网络首发:2026-04-23,
移动端阅览
刘润泽, 丁子淳, 刘晓萱, 张嘉梓, 王锦艳, 宗立率, 韩建华, 蹇锡高. 苯并咪唑/苯并噁唑改性双马来酰亚胺树脂及其在封装基板板材中的应用. 高分子学报, doi: 10.11777/j.issn1000-3304.2026.26019.
Liu, R. Z.; Ding, Z. C.; Liu, X. X.; Zhang, J. Z.; Wang, J. Y.; Zong, L. S.; Han, J. H.; Jian, X. G. Benzimidazole and benzoxazole modified bismaleimide resins for high-performance electronic substrate laminates. Acta Polymerica Sinica (in Chinese), doi: 10.11777/j.issn1000-3304.2026.26019.
刘润泽, 丁子淳, 刘晓萱, 张嘉梓, 王锦艳, 宗立率, 韩建华, 蹇锡高. 苯并咪唑/苯并噁唑改性双马来酰亚胺树脂及其在封装基板板材中的应用. 高分子学报, doi: 10.11777/j.issn1000-3304.2026.26019. DOI: CSTR: 32057.14.GFZXB.2026.7583.
Liu, R. Z.; Ding, Z. C.; Liu, X. X.; Zhang, J. Z.; Wang, J. Y.; Zong, L. S.; Han, J. H.; Jian, X. G. Benzimidazole and benzoxazole modified bismaleimide resins for high-performance electronic substrate laminates. Acta Polymerica Sinica (in Chinese), doi: 10.11777/j.issn1000-3304.2026.26019. DOI: CSTR: 32057.14.GFZXB.2026.7583.
先进电子封装向薄型化与高密度发展,使基板刚性不足和热膨胀系数(CTE)失配问题凸显,亟需开发高刚性、低CTE的新型树脂体系. 本研究使用含苯并咪唑和苯并噁唑结构的二胺单体(APBIA和APBOA),用于改性双马来酰亚胺/烯丙基酚(BDM/DABP)树脂体系. 通过示差热扫描量热(DSC)分析、流变性能测试、傅里叶变换红外光谱分析(FTIR)、动态热机械(DMA)分析、热重分析(TGA)、静态热机械(TMA)分析及力学与介电性能测试等系统研究了其固化行为与多尺度性能. 结果表明,APBIA和APBOA的引入显著促进固化反应,并通过刚性杂环与多重氢键协同作用,有效提升弯曲模量并大幅降低热膨胀系数(CTE最低达8.59×10
-6
℃
-1
). 其中,APBOA改性体系因固化动力学适中,其制备的复材板展现出优异的弯曲强度(576.1 MPa);同时,其铜箔剥离强度提升至0.898 N·mm
-1
,5 GHz下介电损耗低至0.00829,吸水率降至0.818%. 研究表明,苯并咪唑与苯并噁唑
结构可作为高效功能单元,为开发高性能电子封装基板材料提供新思路.
Advanced electronic packaging is moving toward thinner and higher-density designs
exacerbating issues of insufficient substrate rigidity and coefficient of thermal expansion (CTE) mismatch—driving the need for novel resin systems with high rigidity and low CTE. In this work
diamine monomers containing benzimidazole and benzoxazole moieties—namely
2-(4-aminophenyl)-5-aminobenzimidazole (APBIA) and 2-(4-aminophenyl)-5-aminobenzoxazole (APBOA)—were employed to modify a bismaleimide/allylphenol (BDM/DABP) resin system. The curing behavior and multiscale properties of the resulting composites were systematically investigated through a suite of analytical techniques
including differential scanning calorimetry (DSC)
rheology
in situ
Fourier-transform infrared spectroscopy (FTIR)
dynamic mechanical analysis (DMA)
thermogravimetric analysis (TGA)
thermomechanical analysis (TMA)
as well as mechanical and dielectric performance evaluations. The results demonstrate that the incorporation of APBIA and APBOA significantly accelerates the curing reaction. Moreover
the synergistic e
ffect of rigid heterocyclic structures and multiple hydrogen bonds effectively enhances the flexural modulus while substantially reducing the CTE—reaching a minimum value of 8.59×10
-6
℃
-1
. Notably
the APBOA-modified system
benefiting from its balanced curing kinetics
yields composite laminates with outstanding flexural strength (576.1 MPa). Additionally
it achieves a copper foil peel strength of 0.898 N·mm
-1
an ultralow dielectric loss of 0.00829 at 5 GHz
and a reduced water absorption of 0.818%. This study highlights that benzimidazole and benzoxazole architectures can serve as highly effective functional units
offering a promising new strategy for the development of high-performance electronic packaging substrate materials.
Chen G. L. ; Wang G. Q. ; Wang Z. Z. ; Wang L. J. Electronic chip package and co-packaged optics (CPO) technology for modern AI era: a review . Micromachines , 2025 , 16 ( 4 ), 431 . doi: 10.3390/mi16040431 http://dx.doi.org/10.3390/mi16040431
Liu D. ; Bai T. Y. ; Qiao Y. Y. ; Dong W. ; Zhao N. Long-term dynamic stability of the interfacial Cu 6Sn5 inSACtexture305/Cu joints by laser jet solder ball bonding for advanced packaging. ACS Appl. Mater. Interfaces , 2025 , 17 ( 10 ), 16268 - 16274 . doi: 10.1021/acsami.4c22954 http://dx.doi.org/10.1021/acsami.4c22954
Sun X. Y. ; Zhang X. ; Lin Q. S. ; Huang Y. P. ; Xie B. B. ; Ge Q. ; Zhu J. X. ; Wu Y. D. ; Li Q. Study on photothermal dual curing resin used in electronic packaging with inkjet 3D printing . Mater. Today Commun. , 2025 , 45 , 112424 . doi: 10.1016/j.mtcomm.2025.112424 http://dx.doi.org/10.1016/j.mtcomm.2025.112424
Chen H. ; Zhang Q. J. ; Shi Y. ; Yang Y. P. ; Yin Z. L. ; Liu M. ; Zhou Q. A novel cyano-functionalized allylic monomer for enhanced thermal and mechanical performance in bismaleimide resins and composites . Polymer , 2025 , 333 , 128604 . doi: 10.1016/j.polymer.2025.128604 http://dx.doi.org/10.1016/j.polymer.2025.128604
Li Y. J. ; Zhang F. H. ; Liu Y. J. ; Leng J. S. 4D printed shape memory bismaleimide resin with high storage modulus and low shrinkage rate via second-stage curing . Chem. Eng. J. , 2024 , 491 , 152196 . doi: 10.1016/j.cej.2024.152196 http://dx.doi.org/10.1016/j.cej.2024.152196
Ling Y. Q. ; Qiu B. W. ; Lei X. ; Shen L. ; Jin H. ; Zhang X. ; Liang M. ; Chen Y. ; Zou H. W. Improvement of silicon and epoxy phase interface by constructing rigid interpenetrating networks based on bismaleimide to enhance ablative, mechanical and thermal properties . Compos. Part B Eng. , 2024 , 284 , 111675 . doi: 10.1016/j.compositesb.2024.111675 http://dx.doi.org/10.1016/j.compositesb.2024.111675
Lyu J. J. ; Tang J. ; Ji B. B. ; Wu N. ; Liao W. ; Yin C. P. ; Bai S. X. ; Xing S. L. Fluorinated polyetherimide as the modifier for synergistically enhancing the mechanical, thermal and dielectric properties of bismaleimide resin and its composites . Compos. Commun. , 2024 , 51 , 102035 . doi: 10.1016/j.coco.2024.102035 http://dx.doi.org/10.1016/j.coco.2024.102035
Peng H. K. ; Wang Y. C. ; Zhan Y. Q. ; Lei F. ; Wang P. ; Li K. ; Li Y. ; Yang X. L. Hierarchical curing mechanism in epoxy/bismaleimide composites: Enhancing mechanical properties without compromising thermal stabilities . Eur. Polym. J. , 2025 , 222 , 113604 . doi: 10.1016/j.eurpolymj.2024.113604 http://dx.doi.org/10.1016/j.eurpolymj.2024.113604
Zhou Y. F. ; Wang C. L. ; Qiu S. L. ; Hu W. Z. ; Hu Y. ; Zhang L. B. Multifunctional linear polyphosphazene with reactive side groups: achieving fire resistance and low dielectric bismaleimide . Compos. Part B Eng. , 2025 , 296 , 112254 . doi: 10.1016/j.compositesb.2025.112254 http://dx.doi.org/10.1016/j.compositesb.2025.112254
Zhu X. Y. ; Yin S. K. ; Liu L. L. ; Yi W. Z. ; Luo G. ; Zhao Z. H. ; Chen W. Effects of temperature on mechanical properties and impact resistance of carbon fiber/bismaleimide resin composites . J. Mater. Res. Technol. , 2025 , 34 , 2553 - 2569 . doi: 10.1016/j.jmrt.2024.12.258 http://dx.doi.org/10.1016/j.jmrt.2024.12.258
Guo Y. B. ; Wang Z. ; Bi S. Y. ; Sun Q. ; Lu Y. X. Design and regulation of electromagnetic parameters of THz absorbing epoxy resin composite film for 6G electronic packaging . Mater. Today Phys. , 2025 , 51 , 101655 . doi: 10.1016/j.mtphys.2025.101655 http://dx.doi.org/10.1016/j.mtphys.2025.101655
Qian Z. Z. ; Zhu X. F. ; Chen Z. Y. ; Li B. ; Yang G. W. ; Wu G. P. Halogen-free epoxy with enhanced corrosion resistance for microelectronics packaging via γ SN2 nucleophilic substitution . Chem. Mater. , 2025 , 37 ( 9 ), 3311 - 3318 . doi: 10.1021/acs.chemmater.5c00097 http://dx.doi.org/10.1021/acs.chemmater.5c00097
Zheng Z. Y. ; Deng K. ; Liu Y. ; Zhang H. B. ; Wu W. J. ; Wan Y. J. ; Sun R. ; Zhu P. L. Electrical insulation EMI shielding epoxy-based composites with low thermal expansion for advanced electronic packaging . Compos. Sci. Technol. , 2026 , 273 , 111420 . doi: 10.1016/j.compscitech.2025.111420 http://dx.doi.org/10.1016/j.compscitech.2025.111420
Hou T. Q. ; He C. ; Lin Y. ; Zhao Y. S. ; Ding L. J. Low-temperature curing polyimide composites with low coefficient of thermal expansion for high-temperature electronic packaging . Nano Res. , 2025 , 18 ( 5 ), 94907310 . doi: 10.26599/nr.2025.94907310 http://dx.doi.org/10.26599/nr.2025.94907310
Tian J. L. ; Lv X. L. ; Wang W. T. ; Li J. H. ; Zhang J. L. ; Liu J. ; Zhao C. ; Zhang G. P. ; Sun R. Design and synthesis of novel diamines for ultra low-temperature curable polyimides with enhanced copper adhesion . Chem. Eng. J. , 2025 , 525 , 169853 . doi: 10.1016/j.cej.2025.169853 http://dx.doi.org/10.1016/j.cej.2025.169853
Wang H. Q. ; Zhang Y. ; Lv X. L. ; Li J. H. ; Wang K. Y. ; Zhang G. P. ; Sun R. Synthesis and properties of a novel perfluorinated polyimide with high toughness, low dielectric constant and low dissipation factor . Ind. Chem. Mater. , 2025 , 3 ( 5 ), 587 - 595 . doi: 10.1039/d5im00048c http://dx.doi.org/10.1039/d5im00048c
Ji S. Y. ; Jin C. E. ; Wang F. ; Zhu Y. P. ; Qi H. M. Enhancing heat resistance and dielectric properties of cyanate ester resins via incorporation of a fluoride-containing tetrafunctional cyanate ester structure . Polym. Eng. Sci. , 2026 , 66 ( 1 ), 339 - 352 . doi: 10.1002/pen.70215 http://dx.doi.org/10.1002/pen.70215
Zhao D. ; Chen D. ; Ma Y. H. ; Yang W. T. Bismaleimide and biobased limonene copolymer microspheres as reactive fillers to fabricate low- k , high-toughness cyanate ester resin composites . ACS Appl. Polym. Mater. , 2024 , 6 ( 8 ), 4912 - 4923 . doi: 10.1021/acsapm.4c00667 http://dx.doi.org/10.1021/acsapm.4c00667
Zhang B. L. ; Liu F. ; Chen S. T. ; Huang L. K. ; Zhong Y. Y. ; Fan W. ; Li J. W. Fluorine bismaleimide resin with outstanding piezoelectric characteristics for Structure-Function integrated composites . Chem. Eng. J. , 2025 , 503 , 158506 . doi: 10.1016/j.cej.2024.158506 http://dx.doi.org/10.1016/j.cej.2024.158506
Zhou Y. F. ; Ye W. B. ; Liu W. ; Chu F. K. ; Hu W. Z. ; Song L. ; Hu Y. Phosphononitrile based bismaleimide electronic packaging substrate with both fire safety and dielectric properties: assisting 5G communication . Compos. Part B Eng. , 2024 , 280 , 111489 . doi: 10.1016/j.compositesb.2024.111489 http://dx.doi.org/10.1016/j.compositesb.2024.111489
Jiang X. ; Chu F. K. ; Zhou X. ; Li X. J. ; Jia P. F. ; Luo X. Y. ; Hu Y. ; Hu W. Z. Construction of bismaleimide resin with enhanced flame retardancy and mechanical properties based on a novel DOPO-derived bismaleimide monomer . J. Colloid Interface Sci. , 2022 , 614 , 629 - 641 . doi: 10.1016/j.jcis.2022.01.152 http://dx.doi.org/10.1016/j.jcis.2022.01.152
Zhang Z. W. ; Tian D. ; Niu Z. Q. ; Zhou Y. J. ; Hou X. ; Ma X. Y. Enhanced toughness and lowered dielectric loss of reactive POSS modified bismaleimide resin as well as the silica fiber reinforced composites . Polym. Compos. , 2021 , 42 ( 12 ), 6900 - 6911 . doi: 10.1002/pc.26349 http://dx.doi.org/10.1002/pc.26349
Zhou X. ; Chu F. K. ; Qiu S. L. Effects of phenylphosphonate and aliphatic phosphonate structures on the flame retardant performance of bismaleimide . Polym. Degrad. Stab. , 2022 , 205 , 110143 . doi: 10.1016/j.polymdegradstab.2022.110143 http://dx.doi.org/10.1016/j.polymdegradstab.2022.110143
Jiang X. ; Chu F. K. ; Liu W. ; Hu Y. ; Hu W. Z. ; Song L. An individualized core-shell architecture derived from covalent triazine frameworks: toward enhancing the flame retardancy, smoke release suppression, and toughness of bismaleimide resin . ACS Materials Lett. , 2023 , 5 ( 2 ), 630 - 637 . doi: 10.1021/acsmaterialslett.2c01173 http://dx.doi.org/10.1021/acsmaterialslett.2c01173
Ambika Devi K. ; Reghunadhan Nair C. P. ; Ninan K. N. Diallyl bisphenol A: novolac epoxy system cocured with bisphenol-A-bismaleimide: cure and thermal properties . J. Appl. Polym. Sci. , 2007 , 106 ( 2 ), 1192 - 1200 . doi: 10.1002/app.26734 http://dx.doi.org/10.1002/app.26734
Devi K. A. ; Reghunadhan Nair C. P. ; Ninan K. N. Studies on bismaleimide co-cured Novolac epoxy-diallyl bisphenol-A system . Compos. Interfaces , 2008 , 15 ( 7-9 ), 807 - 827 . doi: 10.1163/156855408786778456 http://dx.doi.org/10.1163/156855408786778456
Han X. C. ; Yuan L. ; Gu A. J. ; Liang G. Z. Development and mechanism of ultralow dielectric loss and toughened bismaleimide resins with high heat and moisture resistance based on unique amino-functionalized metal-organic frameworks . Compos. Part B Eng. , 2018 , 132 , 28 - 34 . doi: 10.1016/j.compositesb.2017.07.087 http://dx.doi.org/10.1016/j.compositesb.2017.07.087
Li Z. M. ; Yang M. B. ; Huang R. ; Zhang M. D. ; Feng J. M. Bismaleimide resin modified with diallyl bisphenol A and diallyl p-phenyl diamine for resin transfer molding . J. Appl. Polym. Sci. , 2001 , 80 ( 12 ), 2245 - 2250 . doi: 10.1002/app.1328 http://dx.doi.org/10.1002/app.1328
Liu C. ; Jia H. ; Li N. ; Qiao Y. ; Weng Z. H. ; Du G. Z. ; Jian X. G. Enhanced toughness and thermal properties of bismaleimide resin based on the synergistic effect of reactive amino-terminal poly(phthalazinone ether nitrile sulfone) and bisallyl bearing diphenol group . Polym. Adv. Technol. , 2021 , 32 ( 3 ), 1205 - 1213 . doi: 10.1002/pat.5169 http://dx.doi.org/10.1002/pat.5169
Zhang Z. L. ; Zhang K. ; Xie K. L. ; Bao Y. ; Li X. H. ; Huang J. T. ; Li X. J. ; Wei W. Improvement in toughness and flame retardancy of bismaleimide/diallyl bisphenol A resin with a eugenol allyl ether-grafted polysiloxane . Eur. Polym. J. , 2022 , 180 , 111594 . doi: 10.1016/j.eurpolymj.2022.111594 http://dx.doi.org/10.1016/j.eurpolymj.2022.111594
Wang K. X. ; Wang Y. Y. ; Chen P. ; Xia L. L. ; Xiong X. H. Novel bismaleimide resins modified by allyl compound containing liquid crystalline structure . Adv. Polym. Technol. , 2018 , 37 ( 1 ), 281 - 289 . doi: 10.1002/adv.21667 http://dx.doi.org/10.1002/adv.21667
Yuan Z. G. ; Wang L. ; Liu C. Z. ; Zhang X. G. ; Sun M. M. ; Zhang B. ; Derradji M. ; Li J. H. ; Song C. Y. ; Liu B. Bismaleimide resins modified by a novel vanillin-derived allyl compounds: synthesis, curing behavior, and thermal properties . Polym. Eng. Sci. , 2023 , 63 ( 6 ), 1668 - 1677 . doi: 10.1002/pen.26314 http://dx.doi.org/10.1002/pen.26314
Su Y. C. ; Wang F. ; Zhu Y. P. ; Qi H. M. Preparation and characterization of a novel allyl ether naphthalene phenolic modified bismaleimide resin and its composites . J. Appl. Polym. Sci. , 2024 , 141 ( 33 ), e 55839 . doi: 10.1002/app.55839 http://dx.doi.org/10.1002/app.55839
Li J. J. Sucrose-derived imine synergistic multihydrogen bonds enable tough, strong, and rapid curing phenolic resins . ACS Sustainable Chem. Eng. , 2026 , 14 ( 1 ), 788 - 800 . doi: 10.1021/acssuschemeng.5c11855 http://dx.doi.org/10.1021/acssuschemeng.5c11855
Li W. J. ; Mo R. B. ; Liu W. W. ; Jiang X. ; Zhang X. Y. High-strength self-healing moisture-curable polyurethane enabled by synergistic dynamic disulfide bonds and multiple hydrogen bonds . Polymer , 2025 , 336 , 128927 . doi: 10.1016/j.polymer.2025.128927 http://dx.doi.org/10.1016/j.polymer.2025.128927
Zheng W. ; Zhang C. S. ; Han Y. J. ; Wang W. P. ; Li Z. B. Highly durable silicone-based elastomers achieved through the synergy of bi-incompatible soft segments and multi-scale hydrogen bonds . Small , 2024 , 20 ( 34 ), 2402124 . doi: 10.1002/smll.202402124 http://dx.doi.org/10.1002/smll.202402124
Xiao P. ; He X. J. ; Lu Q. H. Ultra-heat resistance and low CTE polyimides with spirobis(indene)bis(benzoxazole)-benzimidazole unite for flexible substrate applications . Eur. Polym. J. , 2025 , 231 , 113923 . doi: 10.1016/j.eurpolymj.2025.113923 http://dx.doi.org/10.1016/j.eurpolymj.2025.113923
Tian X. ; Wang S. ; Li J. S. ; Liu F. X. ; Wang X. ; Chen H. ; Wang D. ; Ni H. Z. ; Wang Z. Benzimidazole grafted polybenzimidazole cross-linked membranes with excellent PA stability for high-temperature proton exchange membrane applications . Appl. Surf. Sci. , 2019 , 465 , 332 - 339 . doi: 10.1016/j.apsusc.2018.09.170 http://dx.doi.org/10.1016/j.apsusc.2018.09.170
Chen H. Q. ; Dai F. N. ; Wang M. X. ; Chen C. H. ; Qian G. T. ; Yu Y. H. Polyimides containing a novel bisbenzoxazole with high T g and low CTE . RSC Adv. , 2021 , 11 ( 28 ), 16924 - 16930 . doi: 10.1039/d1ra02218k http://dx.doi.org/10.1039/d1ra02218k
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