CN112745503A - 改性双马来酰亚胺树脂及其制备方法、预浸材、铜箔基板及印刷电路板 - Google Patents
改性双马来酰亚胺树脂及其制备方法、预浸材、铜箔基板及印刷电路板 Download PDFInfo
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- CN112745503A CN112745503A CN202010086629.8A CN202010086629A CN112745503A CN 112745503 A CN112745503 A CN 112745503A CN 202010086629 A CN202010086629 A CN 202010086629A CN 112745503 A CN112745503 A CN 112745503A
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- bismaleimide resin
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Abstract
本发明公开一种改性双马来酰亚胺树脂、预浸材、铜箔基板及印刷电路板,其中改性双马来酰亚胺树脂是由特殊结构的双胺与马来酸酐反应形成,且其结构中存在较多的非极性和疏水性基团。改性双马来酰亚胺树脂与一般结构的双马来酰亚胺树脂比较,具有更好的机械和电气特性、耐热性、溶剂溶解性和加工成型性,而能够满足目标应用的需求,例如达到铜箔基板所需小于0.003的介电损耗。
Description
技术领域
本发明涉及一种双马来酰亚胺树脂,特别是涉及一种综合性能优异的改性双马来酰亚胺树脂及其应用,例如预浸材、铜箔基板及印刷电路板。
背景技术
近年来,随着电子产品的发展趋势朝向多功能化和小型化,对电路板被各方面的要求也越来越高,于是电路板逐渐走向多层化、布线高密度化、信号传输高速化。高分子材料的介电特性如介电常数(Dk)和介电损耗(Df)是影响信号传输速度及信号质量的重要指针;对于传输速度而言,高分子材料的介电常数值越低,则信号的传输速度越快;对于信号完整性而言,高分子材料的介电损耗值越低,信号在传输过程中的损失越少。在一些应用场合(如高频印刷电路板),高分子材料需要具有很低的介电常数(Dk)和介电损耗(Df);此外,也需要具有高耐热性、良好的成型工艺性以及优异的综合力学性能与耐环境老化性能。
铜箔基板(copper clad laminate,CCL)为印刷电路板主要原料,其组成包括热塑性树脂、补强材及铜箔等。热塑性树脂如聚酰亚胺(PI)、聚苯醚、聚四氟乙烯、聚苯乙烯、超高分子量聚乙烯、聚苯硫醚、聚醚酮等,虽然具有优异的介电性能和不错的韧性,但是这些树脂的成型工艺性和溶剂溶解性都较差,且因为熔点高、熔体黏度较大及对纤维的黏接性不好而不利于加工,限制了他们的应用范围。另外,环氧树脂、酚醛树脂、不饱和聚酯等因为耐热性和耐湿热性较差、介电损耗较高等原因,也难以满足一些特殊应用场合的要求。
双马来酰亚胺(BMI)由于结构致密刚强,具备优异物理特性及介电性能,包括:热稳定性佳、机械性质强、高玻璃转移温度(Tg)及高的坚硬度(toughness)等,常被使用于铜箔基板。然而,一般结构的双马来酰亚胺树脂的韧性很低、物性很脆,加工性不佳;此外,更因为溶剂溶解性偏低、介电常数偏高而难以应用。
为了提高应用性,BMI必须经过改性。BMI的改性途径较多,有芳香族二元胺和环氧树脂改性BMI、热塑性树脂改性BMI、橡胶改性BMI、含硫化合物改性BMI、烯丙基化合物改性BMI、几种不同结构的BMI共混改性、链延长型BMI以及合成新型BMI等。经过改性的BMI尽管能改善某种特定的特性,但是经常无法兼顾目标应用所需的不同特性;例如,经过改性的BMI在韧性上有所提高,却无法降低介电常数和介电损耗。
发明内容
本发明所要解决的技术问题在于,针对现有技术的不足提供一种改性双马来酰亚胺树脂,其结构中含有更多的非极性和疏水性基团,除了能够在韧性、耐热性和溶剂溶解性上获得改善,并且在电场中不易受到极化,而具有符合预期的低介电特性。本发明另外提供了应用此改性双马来酰亚胺树脂的预浸材、铜箔基板及印刷电路板。
为了解决上述的技术问题,本发明所采用的其中一技术方案是,提供一种改性双马来酰亚胺树脂,其特征在于,所述改性双马来酰亚胺树脂的结构如下式(1)所示:
式(1)中,R为下式(2)至式(4)所示分子团的其中一个:
式(2)中,X为碳原子或以下分子团的其中一个:
式(3)中,Y为以下分子团的其中一个:
其中,R1及R2各自独立为苯甲基或具有1至10个碳原子的烷基:
式(4)中,Z为氧原子、碳原子或以下分子团的其中一个:
其中,R3至R5各自独立为具有1至10个碳原子的烷基;n为0至20之间的正整数。
在本发明的一实施例中,在10GHz下所述改性双马来酰亚胺树脂的介电常数(Dk)小于2.6且介电损耗(Df)小于0.003,且所述改性双马来酰亚胺树脂的玻璃转移温度大于250℃。
本发明还提供一种预浸材,其是将包含具有前述化学结构的改性双马来酰亚胺树脂的一树脂材料施加于一基材上,并经干燥而形成。
本发明还提供一种铜箔基板,其包括一基于具有前述化学结构的改性双马来酰亚胺树脂的预浸材以及一形成于所述预浸材上的铜箔层。
本发明还提供一种印刷电路板,其是将具有前述构造的铜箔基板的所述铜箔层图案化而形成。
为了解决上述的技术问题,本发明所采用的另外一技术方案是,提供一种改性双马来酰亚胺树脂,其特征在于,所述改性双马来酰亚胺树脂的结构如下式(1)所示:
式(1)中,R为下式(5)所示的分子团:
为了解决上述的技术问题,本发明所采用的另外再一技术方案是,提供一种具有前述化学结构的改性双马来酰亚胺树脂的制备方法,其包括:提供一反应器,其内设有一搅拌混合器;将一反应溶液置入所述反应器内,所述反应溶液包含具有非极性骨干结构的双胺、马来酸酐以及一溶剂,其中具有非极性骨干结构的双胺与马来酸酐的摩尔比为1:2-3;启动所述搅拌混合器以均匀混合所述反应溶液,并向所述反应溶液中加入触媒;以及在常压及90℃至150℃的反应温度下下进行合成反应12至25小时,得到一黏稠状树脂溶液。
在本发明的一实施例中,所述改性双马来酰亚胺树脂的制备方法还包括从所述黏稠状树脂溶液中析出所述改性双马来酰亚胺树脂,并去除不纯物。
在本发明的一实施例中,所述反应溶液的固含量为40wt%至60wt%。
在本发明的一实施例中,所述溶剂为丙酮、N,N-二甲基甲酰胺(DMF)或甲苯,所述触媒包含醋酸、醋酸钠以及三乙胺。
本发明的改性双马来酰亚胺树脂,与一般双马来酰亚胺树脂相较,具有下列有益特性:
1.改性双马来酰亚胺树脂因为具有特殊的化学结构而能够提高韧性、降低脆性,提高耐热性,以及增加于溶剂中的溶解量;改性双马来酰亚胺树脂对丙酮的溶剂溶解率至少为25%。
2.改性双马来酰亚胺树脂的结构中存在较多的非极性和疏水性基团,使得其在电场中不易受到极化,从而可达到优异的低介电特性;在10GHz下改性双马来酰亚胺树脂的介电常数(Dk)小于2.6且介电损耗(Df)小于0.003;
3.改性双马来酰亚胺树脂具有大于250℃的玻璃转移温度(Tg)。
本发明的改性双马来酰亚胺树脂可以和其他具不饱和基的化合物混用,以达到目标应用(如铜箔基板)所需的特性,例如更佳的耐热性、韧性,或更低的介电常数和介电损耗。
为使能更进一步了解本发明的特征及技术内容,请参阅以下有关本发明的详细说明与附图,然而所提供的附图仅用于提供参考与说明,并非用来对本发明加以限制。
附图说明
图1为本发明的改性双马来酰亚胺树脂的制备方法的流程图。
图2为本发明的预浸材的制造过程示意图。
图3为本发明的预浸材的结构示意图。
图4为本发明的覆金属基板的制造过程示意图。
图5为本发明的印刷电路板的结构示意图。
具体实施方式
以下是通过特定的具体实施例来说明本发明所公开有关“改性双马来酰亚胺树脂、预浸材、覆金属基板及印刷电路板”的实施方式,本领域技术人员可由本说明书所公开的内容了解本发明的优点与效果。本发明可通过其他不同的具体实施例加以施行或应用,本说明书中的各项细节也可基于不同观点与应用,在不悖离本发明的构思下进行各种修改与变更。另外,本发明的附图仅为简单示意说明,并非依实际尺寸的描绘,事先声明。以下的实施方式将进一步详细说明本发明的相关技术内容,但所公开的内容并非用以限制本发明的保护范围。
应当可以理解的是,虽然本文中可能会使用到“第一”、“第二”、“第三”等术语来描述各种组件或者信号,但这些组件或者信号不应受这些术语的限制。这些术语主要是用以区分一组件与另一组件,或者一信号与另一信号。另外,本文中所使用的术语“或”,应视实际情况可能包括相关联的列出项目中的任一个或者多个的组合。
为了改善双马来酰亚胺树脂的机械和电气特性、耐热性、溶剂溶解性和加工成型性,以满足目标应用的需求,本发明使用具有非极性骨干结构的双胺与马来酸酐进行有机反应,使得双马来酰亚胺树脂的结构中存在较多的非极性和疏水性基团。
本发明的改性双马来酰亚胺树脂具有下式(1)所示的结构:
式(1)中,R为下式(2)至式(4)所示分子团的其中一个:
式(2)中,X为碳原子或以下分子团的其中一个:
式(3)中,Y为以下分子团的其中一个:
其中,R1及R2各自独立为苯甲基或具有1至10个碳原子的烷基:
式(4)中,Z为氧原子、碳原子或以下分子团的其中一个:
其中,R3至R5各自独立为具有1至10个碳原子的烷基;n为0至20之间的正整数。
在一些实施例中,X为下式(5)所示的分子团:
值得一提的是,本发明的改性双马来酰亚胺树脂,因为具有特殊的化学结构而能够提高韧性、降低脆性,提高耐热性,以及增加于溶剂中的溶解量。此外,改性双马来酰亚胺树脂的结构中存在较多的非极性和疏水性基团,使得其在电场中不易受到极化,从而可达到优异的低介电特性。此外,改性双马来酰亚胺树脂具有高玻璃转移温度(Tg)。进一步而言,在10GHz下改性双马来酰亚胺树脂的介电常数(Dk)小于2.6且介电损耗(Df)小于0.003;改性双马来酰亚胺树脂的玻璃转移温度大于250℃;改性双马来酰亚胺树脂对丙酮的溶剂溶解率至少为25%。
根据实际需要,改性双马来酰亚胺树脂可以和其他具不饱和基的化合物混用,以达到目标应用(如铜箔基板)所需的特性,例如更佳的耐热性、韧性,或更低的介电常数和介电损耗。具不饱和基的化合物的具体例包括:乙烯、丙烯、苯乙烯、二乙烯基苯、二乙烯基联苯等乙烯基化合物;(甲基)丙烯酸甲酯、(甲基)丙烯酸2-羟基乙酯、(甲基)丙烯酸2-羟基丙酯、聚丙二醇二(甲基)丙烯酸酯、三羟甲基丙烷二(甲基)丙烯酸酯、三羟甲基丙烷三(甲基)丙烯酸酯、新戊四醇四(甲基)丙烯酸酯、二新戊四醇六(甲基)丙烯酸酯等一元或多元醇的(甲基)丙烯酸酯类;双酚A型环氧(甲基)丙烯酸酯、双酚F型环氧(甲基)丙烯酸酯等环氧(甲基)丙烯酸酯类;以及苯并环丁烯树脂。该等具不饱和基的化合物可使用1种或混用2种以上。
参阅图1所示,本发明的改性双马来酰亚胺树脂可由以下步骤制备得到:步骤S1,提供一反应器;步骤S2,将反应原料按计量投入反应器,反应合成双马来酰亚胺;以及步骤S3,反应产物析出纯化。
进一步而言,反应器内部设有一搅拌混合器。步骤S2中,反应原料以反应溶液的形式存在,其主要包括具有非极性骨干结构的双胺、马来酸酐及溶剂。反应溶液的固含量为10wt%至60wt%,且优选为40wt%至60wt%;其中双胺与马来酸酐的摩尔比为1:2-3,溶剂为极性非质子溶剂,其可选自丙酮、N,N-二甲基甲酰胺(DMF)及甲苯中的至少一种。
合成反应在常压、反应温度为室温至200℃的条件下,以及触媒和脱水剂的存在下进行;反应1至3小时后,会先有双马来酰亚胺酸生成,继续反应1至5小时,就会有双马来酰亚胺树脂存在于反应溶液中。触媒可以滴加方式加入反应溶液中,触媒可选自醋酸、醋酸钠及三乙胺,优选同时包含醋酸、醋酸钠及三乙胺。优选在进行合成反应之前向反应器输入氮气,以去除反应器内的空气和水气。然而,这些细节只是本实施例所提供可行的实施方式,而并非用以限定本发明。
步骤S2中,可采用下式(6)至式(10)所示的具有非极性骨干结构的双胺:
步骤S3中,先向反应溶液加入适量的去离子水,再启动搅拌混合器搅拌一段时间,使树脂颗粒或溶液逐渐析出;析出后的反应溶液经过滤、真空干燥后即得到双马来酰亚胺树脂。
实验例1
取47.7g(等同于0.2mol)双胺A与43.1g(等同于0.44mol)马来酸酐,并将其溶于300ml丙酮中;将所形成的反应溶液投入内部设有搅拌混合器的500ml四颈圆底反应烧瓶,向反应烧瓶通入氮气以去除空气及水气;在常压下,启动搅拌混合器,以300rpm的转速将反应溶液均匀混合。
当反应温度达到80℃时,反应溶液中的固成分会全部溶解而呈现清澈的红褐色;此时,以滴加方式将4g醋酸钠、140ml醋酸酐与28ml三乙胺加入于反应溶液中,反应温度设定在90℃,反应时间为12小时,反应完成后反应溶液由清澈的红褐色转变为黏绸的红褐色(反应溶液很黏绸)。此后,进行析出纯化工艺,从深红褐色的反应溶液中析出浅棕色树脂颗粒,再将未反应单体、残留酸等不纯物去除,得到高纯度的80g红褐色双马来酰亚胺树脂颗粒(下称BMI-A树脂)。取BMI-A树脂制成铜箔基板进行测试,结果如表2所示。
实验例2
制备方法和反应条件与实施例1相同,差别在于:取69.7g双胺B与43.1g马来酸酐作为聚合反应单体,并将其溶于245ml MF中;所形成的反应溶液中加入4.5g醋酸钠、152ml醋酸酐与30ml三乙胺作为触媒;以及反应时间改为20小时。最后得到高纯度的85g深褐色双马来酰亚胺树脂颗粒(下称BMI-B树脂)。取BMI-A树脂制成铜箔基板进行测试,结果如表2所示。
实验例3
制备方法和反应条件与实施例1相同,差别在于:取69.2g双胺C与43.1g马来酸酐作为聚合反应单体,并将其溶于266ml MF中;所形成的反应溶液中加入3.4g醋酸钠、130ml醋酸酐与35ml三乙胺作为触媒;以及反应温度改为120℃且反应时间改为15小时。最后得到高纯度的90g红褐色双马来酰亚胺树脂颗粒(下称BMI-C树脂)。取BMI-C树脂制成铜箔基板进行测试,结果如表2所示。
实验例4
制备方法和反应条件与实施例1相同,差别在于:取75.3g双胺D与43.1g马来酸酐作为聚合反应单体,并将其溶于270ml甲苯中;所形成的反应溶液中加入4.7g醋酸钠、132ml醋酸酐与40ml三乙胺作为触媒;以及反应温度改为150℃且反应时间改为18小时。最后得到高纯度的83g红褐色双马来酰亚胺树脂颗粒(下称BMI-D树脂)。取BMI-D树脂制成铜箔基板进行测试,结果如表2所示。
实验例5
制备方法和反应条件与实施例1相同,差别在于:取86.9g双胺E与43.1g马来酸酐作为聚合反应单体,并将其溶于430ml甲苯中;所形成的反应溶液中加入3g醋酸钠、156ml醋酸酐与44ml三乙胺作为触媒;以及反应温度改为100℃且反应时间改为25小时。最后得到高纯度的95g浅黄色双马来酰亚胺树脂颗粒(下称BMI-E树脂)。取BMI-E树脂制成铜箔基板进行测试,结果如表2所示。
比较例使用双(3-乙基-5-甲基-4-马来酰亚胺苯基)甲烷(BMI-5100,大和化成工业公司制)制成铜箔基板进行测试,结果如表2所示。
表1
表2
表2中关键特性的测试方法如下:
1.玻璃转移温度(℃):以示差扫瞄热分析仪(DSC)TA2100测试。
2.介电常数(Dk)和损耗因子(Df):以介电分析仪(Dielectric Analyzer)HPAgilent E4991A测试在频率10GHz的介电常数和损耗因子。
3.溶剂溶解性:将树脂溶解于丙酮溶剂,测试其溶解量,以重量百分比表示。
参阅图2及图3所示,本发明的改性双马来酰亚胺树脂可用于制作预浸材1;预浸材1可以是将含有改性双马来酰亚胺树脂的树脂材料12施加于一基材11(如绝缘纸、玻璃纤维布或其他纤维材料)上,并经干燥而形成。进一步而言,树脂材料12可以树脂清漆的形式存在,且树脂材料12的施加方式可以是涂布或含浸;带有树脂材料12的基材11可以在适当的温度下进行干燥处理,经过一段时间后形成半硬化状态的预浸材1。
树脂材料12可进一步包含功能性添加剂,以提高实际应用时所需的各种特性,功能性添加剂可选自阻燃剂、溶剂、填充剂及硬化促进剂中的至少一种。
参阅图4所示,前述的预浸材1可用于制作铜箔基板C。进一步而言,铜箔基板C可以是在至少一片预浸材1的单片或双面层迭铜箔层2,然后进行热压合而形成;热压合条件没有特别的限制,可以根据树脂材料的组成做调整。
参阅图5所示,前述的铜箔基板C可用于制作印刷电路板P。进一步而言,印刷电路板P可以是将铜箔基板C的铜箔层2图案化而形成,即使铜箔层2具有特定的线路图案而形成线路层2’;图案化的方式可以是微影蚀刻,但不限于此。
以上所公开的内容仅为本发明的优选可行实施例,并非因此局限本发明的权利要求书的保护范围,所以凡是运用本发明说明书及附图内容所做的等效技术变化,均包含于本发明的权利要求书的保护范围内。
Claims (10)
2.根据权利要求1所述的改性双马来酰亚胺树脂,其特征在于,在10GHz下所述改性双马来酰亚胺树脂的介电常数(Dk)小于2.6且介电损耗(Df)小于0.003,且所述改性双马来酰亚胺树脂的玻璃转移温度大于250℃。
3.一种预浸材,其特征在于,所述预浸材是将包含如权利要求1所述的改性双马来酰亚胺树脂的一树脂材料施加于一基材上,并经干燥而形成。
4.一种铜箔基板,其特征在于,所述铜箔基板包括一如权利要求3所述的预浸材以及一形成于所述预浸材上的铜箔层。
5.一种印刷电路板,其特征在于,所述印刷电路板是将如权利要求4所述的铜箔基板的所述铜箔层图案化而形成。
7.一种根据权利要求1或6所述的改性双马来酰亚胺树脂的制备方法,其特征在于,所述改性双马来酰亚胺树脂的制备方法包括:
提供一反应器,其内设有一搅拌混合器;
将一反应溶液置入所述反应器内,所述反应溶液包含具有非极性骨干结构的双胺、马来酸酐以及一溶剂,其中具有非极性骨干结构的双胺与马来酸酐的摩尔比为1:2-3;
启动所述搅拌混合器以均匀混合所述反应溶液,并向所述反应溶液中加入触媒;以及
在常压及90℃至150℃的反应温度下下进行合成反应12至25小时,得到一黏稠状树脂溶液。
8.根据权利要求7所述的改性双马来酰亚胺树脂的制备方法,其特征在于,所述改性双马来酰亚胺树脂的制备方法还包括从所述黏稠状树脂溶液中析出所述改性双马来酰亚胺树脂,并去除不纯物。
9.根据权利要求7所述的改性双马来酰亚胺树脂的制备方法,其特征在于,所述反应溶液的固含量为40wt%至60wt%。
10.根据权利要求7所述的改性双马来酰亚胺树脂的制备方法,其特征在于,所述溶剂为丙酮、N,N-二甲基甲酰胺(DMF)或甲苯,所述触媒包含醋酸、醋酸钠以及三乙胺。
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