CN105073846B - 二烯/亲二烯体偶合物和具有可再加工性的热固性树脂组合物 - Google Patents
二烯/亲二烯体偶合物和具有可再加工性的热固性树脂组合物 Download PDFInfo
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- CN105073846B CN105073846B CN201480017540.9A CN201480017540A CN105073846B CN 105073846 B CN105073846 B CN 105073846B CN 201480017540 A CN201480017540 A CN 201480017540A CN 105073846 B CN105073846 B CN 105073846B
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Abstract
本发明提供了可用于固定至电路板半导体设备例如芯片尺寸或芯片级封装(“CSP”)、球栅阵列(“BGA”)、栅格阵列(“LGA”)等(统称为“子组件”)或半导体芯片上的热固性树脂组合物。当经历适当的条件时,所述组合物的反应产物可以可控地再加工。
Description
技术领域
本发明提供了可用于固定至电路板半导体设备例如芯片尺寸或芯片级封装(“CSP”)、球栅阵列(“BGA”)、栅格阵列(“LGA”)等(统称为“子组件(subcomponent)”)或半导体芯片(semiconductor chip)上的热固性树脂组合物。当经历适当的条件时,所述组合物的反应产物可以可控地再加工。
背景技术
近年,手持显示设备的普及已使得对它们的需求急剧增加。为了满足日益增长的需求,生产能力的增长因此已受到挑战。对于生产者而言特别成问题的一个领域是对有缺陷的子组件的处理和操作。例如,在电路板装配件(subassembly)的制造期间,许多半导体设备被电连接至所述板。随后可以对所述板进行测试以评价功能。有时,所述板失效。在这样的情况中,期望鉴别导致失效的半导体设备,将其自所述板中移除,并重新使用具有剩余功能半导体设备的板。
通常,通过使用焊料连接(solder connection)(或金属化)将子组件连接至电路板上的电导体。然而,当生成的装配件暴露于热循环、振动、变形、或下落时,电路板和一个或多个子组件之间的焊料连接的可靠性经常变得不可信。将子组件固定在电路板上之后,通常用密封树脂(通常称为底部填充胶(underfill sealant))填充子组件和电路板之间的空间,以释放由热循环导致的应力,由此改善所组装的结构的热冲击性质并增强其可靠性。
然而,由于当固化时形成交联网络的热固性树脂组合物通常用作底部填充胶,在将子组件固定至电路板上之后失效的事件中,难以替换所述子组件而不破坏由此形成的装配件整体或不使由此形成的装配件整体报废。
尽管有现有技术,但期望具有以下特性的底部填充胶:其在子组件或半导体芯片与电路板之间的未充满空间中通过毛细管作用而快速流动;在低温条件下快速固化;提供良好的生产率和热冲击耐性,同时允许与其一起使用的基底易于被加工且在不损害保留在基底上的剩余子组件或半导体芯片或者基底自身的完整性的条件下易于与有缺陷的子组件或半导体芯片分离;且在有缺陷的子组件或半导体芯片一旦被组装至电路板上即失效的事件中可再加工。
发明内容
本发明提供了可用作底部填充胶的热固性树脂组合物。所述组合物使得子组件或半导体芯片能够通过短时间热固化而牢固地连接至电路板并具有良好的生产率,其显示出出色的热冲击性质(或热循环性质),并使得子组件或半导体芯片在子组件或半导体芯片或连接失效的事件中易于自电路板中移除。
这些组合物的反应产物能够通过软化和失去其粘合性而被可控地再加工,例如通过暴露于高于用于固化所述组合物的温度条件的温度条件。
更具体地,在一个方面中,本发明的组合物提供了可固化的树脂组分、固化剂(curative)以及使用至少两个羧酸基团官能化的二烯/亲二烯体偶合物;而在另一个方面中,本发明的组合物提供了可固化的树脂组分、固化剂以及使用至少两个对所述可固化的树脂组分具有反应性的基团(其中至少一个不为羧酸基团)官能化的二烯/亲二烯体偶合物。
在这些方面中的每一个方面中,当暴露于高于用于固化所述组合物的温度条件的温度条件时,本发明的组合物的反应产物可以可控地降解。
尽管本发明的组合物可在相对低的温度下在短时间内固化,但其固化的反应产物具有优异的热冲击性质,且此外可以通过在加热的条件下施加力而容易地分裂(split)。即,通过本发明的热固化树脂组合物的固化反应产物连接至电路板的子组件或半导体芯片可以通过加热所述反应产物而容易地移除。
通过使用本发明的组合物,子组件或半导体芯片可以通过短时间热固而牢固地连接至电路板且具有良好的生产率,生成的装配件表现出优异的热冲击性能(或热循环性质)。此外,在失效的事件中,子组件或半导体芯片可以被容易地移除。这使得可以重新使用电路板,由此获得生产过程的收率的改善且降低生产成本。
在参考附图阅读“具体实施方式”之后,将变得更易于明白本发明的益处和优势。
附图说明
图1描绘了显示半导体设备的实例的剖视图,所述半导体设备中使用了本发明的热固性树脂组合物。
图2描绘了显示半导体倒装芯片部件的实例的剖视图,所述半导体倒装芯片部件中使用了本发明的热固性树脂组合物。
图3描绘了可用于再加工根据本发明的固化的热固性树脂组合物以自已连接半导体设备的电路板中移除所述半导体设备的步骤的流程图。
图4描绘了样品A-D的储能模量随温度变化的轨迹。
图5描绘了样品E和F的储能模量随温度变化的轨迹。
图6描绘了样品L的储能模量随温度变化的轨迹。
图7描绘了样品M的储能模量随温度变化的轨迹。
图8描绘了样品N的储能模量随温度变化的轨迹。
图9描绘了HYSOL UF3808的储能模量随温度变化的轨迹。
图10描绘了表7中所示的各样品的角正切(tan delta)随温度变化的轨迹。
具体实施方式
如上所述,在一个方面中,本发明的组合物提供了可固化的树脂组分、固化剂以及使用至少两个羧酸基团官能化的二烯/亲二烯体偶合物;而在另一个方面中,本发明的组合物提供了可固化的树脂组分、固化剂以及使用至少两个对所述可固化的树脂组分具有反应性的基团(其中至少一个不为羧酸基团)官能化的二烯/亲二烯体偶合物。
二烯/亲二烯体偶合物可以选自双环戊二烯、环戊二烯-马来酰亚胺、环戊二烯-马来酸酯、环戊二烯-富马酸酯、环戊二烯-(甲基)丙烯酸酯、环戊二烯-巴豆酸酯、环戊二烯-肉桂酸酯、环戊二烯-(甲基)丙烯酰胺和呋喃-马来酰亚胺。
二烯/亲二烯体偶合物中的二烯可以选自无环的1,3-二烯、环戊二烯、环己二烯、呋喃、富烯、吡咯、萘和蒽。
二烯/亲二烯体偶合物中的亲二烯体可以选自环戊二烯、马来酰亚胺、异马来酰亚胺、柠康酰亚胺(citraconimide)、衣康酰亚胺、马来酸酯、巴豆酸酯、肉桂酸酯、富马酸酯、(甲基)丙烯酸酯、氰基丙烯酸酯、苯醌、苯醌肟、苯醌亚胺、萘醌、亚烷基丙二酸酯、(甲基)丙烯酰胺、和含吸电子基团的炔。值得注意的是,环戊二烯既可以被认为是二烯又可以被认为是亲二烯体。
二烯/亲二烯体偶合物可以被结构I范围内的化合物包括:
其中X为CH2、C=CH2、C=O、C=S、或C=NR,其中R为H、烷基,芳基或芳烷基;Y为O、S或NR,其中R为H、烷基、芳基或芳烷基;A为亚烷基;Z为H、(甲基)丙烯酰基、缩水甘油基或含可聚合的官能团(functionality)的基团例如环氧基团(除缩水甘油基以外)、环硫化物、(甲基)丙烯酸酯(除(甲基)丙烯酰基以外)、(甲基)丙烯酰胺、马来酰亚胺、马来酸酯、富马酸酯、肉桂酸酯、巴豆酸酯、氧杂环丁烷、硫代氧杂环丁烷、烯丙基、苯乙烯、噁嗪(例如苯并噁嗪)、噁唑啉、N-乙烯基酰胺和乙烯基醚;n为0或1;且m为2-4。
二烯/亲二烯体偶合物可以被结构II范围内的化合物包括:
其中X1和X2相同或不同,且各自独立地选自CH2、C=CH2、C=O、C=S、或C=NR,其中R为H、烷基、芳基或芳烷基;Y1和Y2相同或不同且各自独立地选自O、S或NR,其中R为H、烷基、芳基或芳烷基;A1和A2相同或不同且各自独立地为亚烷基;Z1和Z2相同或不同且各自独立地选自H、(甲基)丙烯酰基、缩水甘油基、或者一个或多个含可聚合的官能团的基团例如环氧基(除缩水甘油基以外)、环硫化物、(甲基)丙烯酸酯(除(甲基)丙烯酰基以外)、(甲基)丙烯酰胺、马来酰亚胺、马来酸酯、富马酸酯、肉桂酸酯、巴豆酸酯、氧杂环丁烷、硫代氧杂环丁烷、烯丙基、苯乙烯、噁嗪(例如苯并噁嗪)、噁唑啉、N-乙烯基酰胺和乙烯基醚;且n1和n2相同或不同且各自独立地为0或1。
结构I范围内的化合物包括具有结构IA-IF的二环戊二烯基(“DCPD”)的二羧酸的异构体,其中X为C=O,Y为O,Z为H且n为0:
其中X为C=O、Y为O、Z为含可聚合的官能团的基团且n为0的结构I范围内的化合物的代表性实例包括由结构A-E表示的化合物(为方便起见,使用单一结构描绘化合物A-E,但与IA-IF所示的那些相似的其它异构体也可以为化合物A-E):
在另一个实施方案中,本发明提供了结构I范围内的化合物,其已通过DCPD二羧酸与二官能环氧化物或多官能环氧树脂以可控的方式的反应链延长;或通过二羧酸与DCPD二环氧化物的反应链延长(结构A)。
其中X为C=O、Y为O且Z为含可聚合的官能团的基团的结构I范围内的化合物的链延长形式的代表性实例包括结构F-H:
其中R1和R2可以相同或不同且各自独立地选自二官能环氧树脂或多官能环氧树脂的主链,且n为1-10;
其中在结构G中,R3为二羧酸主链;且在结构G和H中,n为1-10。在这些链延长的结构F-H范围内,所述结构F-H可以具有DCPD单元的头-头、头-尾或尾-头排列。
其中X为CH2、Y为O、A为CH2、n为1、且Z为H、(甲基)丙烯酰基或缩水甘油基官能团的结构I范围内的化合物的代表性实例分别包括结构J-L:
当Z为H时;
当Z为甲基丙烯酰基时;
当Z为缩水甘油基时。
在另一个实施方案中,提供了由DCPD的二羧酸制备的化合物,其已发生反应以形成被衍生化而具有不同的官能团的化合物。
其中X1和X2各自为C=O、Y1和Y2各自为O、n1和n2各自为0、且Z1为缩水甘油基且Z2为(甲基)丙烯酸酯的结构II范围内的化合物的代表性实例包括结构M:
当然,结构I和II范围内的DCPD衍生物也可以与可固化的树脂组分和固化剂一起使用,以形成热固性树脂组合物。
例如,在另一个方面中,热固性树脂组合物广泛地包含可固化的树脂组分和结构I范围内的化合物
其中X为CH2、C=CH2、C=O、C=S、或C=NR,其中R为H、烷基、芳基或芳烷基;Y为O、S或NR,其中R为H、烷基、芳基或芳烷基;A为亚烷基;Z为H、(甲基)丙烯酰基、缩水甘油基或含可聚合的官能团的基团例如环氧基团(除缩水甘油基以外)、环硫化物、(甲基)丙烯酸酯(除(甲基)丙烯酰基以外)、(甲基)丙烯酰胺、马来酰亚胺、马来酸酯、富马酸酯、肉桂酸酯、巴豆酸酯、氧杂环丁烷、硫代氧杂环丁烷、烯丙基、苯乙烯、噁嗪、噁唑啉、N-乙烯基酰胺和乙烯基醚;n为0或1;且m为2-4;
和/或
结构II范围内的化合物:
其中X1和X2相同或不同,且各自独立地选自CH2、C=CH2、C=O、C=S、或C=NR,其中R为H、烷基、芳基或芳烷基;Y1和Y2相同或不同且各自独立地选自O、S或NR,其中R为H、烷基、芳基或芳烷基;A1和A2相同或不同且各自独立地为亚烷基;Z1和Z2相同或不同且各自独立地选自H、(甲基)丙烯酰基、缩水甘油基、或者一个或多个含可聚合的官能团的基团例如环氧基团(除缩水甘油基以外)、环硫化物、(甲基)丙烯酸酯(除(甲基)丙烯酰基以外)、(甲基)丙烯酰胺、马来酰亚胺、马来酸酯、富马酸酯、肉桂酸酯、巴豆酸酯、氧杂环丁烷、硫代氧杂环丁烷、烯丙基、苯乙烯、噁嗪(例如苯并噁嗪)、噁唑啉、N-乙烯基酰胺和乙烯基醚;且n1和n2相同或不同且各自独立地为0或1。
结构I范围内的化合物可以用作固化剂或助熔剂,特别是当Z为氢时。当Z(和/或Z1和/或Z2)为含可聚合的官能团的基团时,结构I和/或II范围内的化合物可用作可固化树脂组分的共反应物。
此外,组合物可以包含以下物质中的一种或多种:橡胶增韧剂、助粘剂、润湿剂、着色剂、消泡剂、和助流剂(flowability agent)。
可固化的树脂组分可以包括基于双酚的环氧树脂例如双酚A、双酚F或双酚S环氧树脂,或者它们的组合。此外,可以使用两种或多种处于相同树脂类型(例如A、F或S)范围内的不同双酚环氧树脂。
本文中期望使用的双酚环氧树脂的可商购的实例包括双酚-F型环氧树脂(例如可购自Nippon Kayaku,Japan的RE-404-S,以及可购自Dai Nappon Ink&Chemicals,Inc.的EPICLON 830(RE1801)、830S(RE1815)、830A(RE1826)和830W,以及可购自Resolution的RSL1738和YL-983U)和双酚-A型环氧树脂(例如可购自Resolution的YL-979和980)。
上述可商购自Dai Nippon的双酚环氧树脂以具有比常规的基于双酚A环氧树脂的环氧树脂低得多的粘度的液体的未稀释的表氯醇-双酚F环氧树脂的形式推广并且具有与液体双酚A环氧树脂相似的物理性质。双酚F环氧树脂具有低于双酚A环氧树脂的粘度,两种类型的环氧树脂之间的其余相同,这提供了较低的粘度,且因此提供了快速流动的底部填充胶材料。
上述可商购自Resolution的双酚环氧树脂以低氯含量液体环氧树脂的形式推广。双酚A环氧树脂具有180和195之间的EEW(g/eq),和25℃下为100和250cps之间的粘度。YL-979的总氯含量报告为500和700ppm之间,且YL-980的总氯含量报告为100和300ppm之间。RSL-1738的总氯含量报告为500和700ppm之间,且YL-983U的总氯含量报告为150和350ppm之间。
除双酚环氧树脂以外,其它环氧化合物也包括在可固化的树脂组分范围内。可以使用例如脂环族环氧树脂例如3,4-环氧环己基甲基-3,4-环氧环己基碳酸酯。此外,还可以使用用于调节粘度和/或降低Tg的单官能、双官能或多官能反应性稀释剂,其实例包括丁基缩水甘油基醚、甲苯基缩水甘油基醚、聚乙二醇缩水甘油基醚或聚丙二醇缩水甘油基醚。
在适用于本文的环氧树脂中还包括酚类化合物的聚缩水甘油基衍生物例如可以商品名EPON例如EPON 828、EPON 1001、EPON 1009、和EPON 1031商购自Resolution的那些;可以商品名DER 331、DER 332、DER 334、和DER 542获自Dow Chemical Co.的那些;和可以商品名BREN-S获自Nippon Kayaku的那些。其他适合的环氧树脂包括由多元醇等制备的聚环氧化物和酚醛清漆的聚缩水甘油基衍生物。后者为例如获自Dow Chemical的DEN431、DEN438、和DEN 439。甲酚类似物也可以以商品名ARALDITE例如ARALDITE ECN 1235、ARALDITEECN 1273、和ARALDITE ECN 1299商购自Ciba Specialty Chemicals Corporation。SU-8为可获自Resolution的双酚-A-型环氧酚醛清漆。胺、氨基醇和聚羧酸的聚缩水甘油基加合物也可用于此发明,其可商购的树脂包括获自F.I.C.Corporation的GLYAMINE 135、GLYAMINE125、和GLYAMINE 115;获自Ciba Specialty Chemicals的ARALDITE MY-720、ARALDITE0500、和ARALDITE 0510;和获自Sherwin-Williams Co.的PGA-X和PGA-C。
用于本文中的适合的单官能环氧共反应物稀释剂包括具有低于环氧树脂组分的粘度的粘度的那些,通常为低于约250cps。
单官能环氧共反应物稀释剂应具有有约6至约28个碳原子的烷基基团的环氧基团,其实例包括C6-28烷基缩水甘油基醚、C6-28脂肪酸缩水甘油基酯和C6-28烷基酚缩水甘油基醚。
在包括这样的单官能环氧共反应物稀释剂的情况下,基于组合物的总重量,共反应物稀释剂应以多至约5重量%至约15重量%例如约8重量%至约12重量%的量使用。
除具有环氧官能团的化合物和树脂以外,还可以使用具有一种或多种以下官能团的化合物和树脂:环硫化物、氧杂环丁烷、硫代氧杂环丁烷、噁嗪(例如苯并噁嗪)、噁唑啉、马来酰亚胺、衣康酰胺(itaconamide)、纳迪酰亚胺(nadimide)、氰酸酯、(甲基)丙烯酸酯、及它们的组合。
具有环硫化物官能团的化合物和树脂可以为任意环氧树脂的硫化的形式。氧杂环丁烷可以为任意环氧树脂的4元含氧环形式及其硫代氧杂环丁烷硫化的形式。
噁嗪,例如苯并噁嗪,可以被以下结构包括
其中o为1-4,X选自直接的键(direct bond)(当o为2时)、烷基(当o为1时)、亚烷基(当o为2-4时)、羰基(当o为2时)、巯基(当o为1时)、硫醚(当o为2时)、亚砜(当o为2时)、或砜(当o为2时),且R1为芳基,或
其中p为2,Y选自联苯基(当p为2时)、二苯基甲烷(当p为2时)、二苯基异丙烷(当p为2时)、二苯硫醚(当p为2时)、二苯基亚砜(当p为2时)、二苯基砜(当p为2时)、或二苯酮(当p为2时),且R4选自氢、卤素、烷基或烯基。
氰酸酯可以选自在各分子上具有至少一个氰酸酯基团的芳基化合物且可以常规地由式Ar(OCN)m表示,其中m为2至5的整数,且Ar为芳香基团。芳香基团Ar应包含至少6个碳原子,且可以衍生自例如芳香烃例如苯、联苯、萘、蒽、芘等。芳香基团Ar也可以衍生自多核芳香烃,其中至少两个芳香环通过桥接基团彼此连接。还包括源自酚醛清漆型酚醛树脂的芳香基团——即这些酚醛树脂的氰酸酯。芳香基团Ar还可以包含其他与环连接的非反应性的取代基。
这样的氰酸酯的实例包括例如1,3-二氰酰苯;1,4-二氰酰苯;1,3,5-三氰酰苯;1,3-、1,4-、1,6-、1,8-、2,6-或2,7-二氰酰萘;1,3,6-三氰酰萘;4,4'-二氰酰-联苯基;双(4-氰酰苯基)甲烷和3,3',5,5'-四甲基双(4-氰酰苯基)甲烷;2,2-双(3,5-二氯-4-氰酰苯基)丙烷;2,2-双(3,5-二溴-4-二氰酰苯基)丙烷;双(4-氰酰苯基)醚;双(4-氰酰苯基)硫化物;2,2-双(4-氰酰苯基)丙烷;三(4-氰酰苯基)-亚磷酸酯;三(4-氰酰苯基)磷酸酯;双(3-氯-4-氰酰苯基)甲烷;氰酸化的酚醛清漆;1,3-双[4-氰酰苯基-1-(甲基亚乙基)]苯和氰酸化的双酚-封端的聚碳酸酯或其他热塑性寡聚体。
具有(甲基)丙烯酸酯官能团的化合物和树脂可以选自许多材料例如由H2C=CGCO2R1表示的那些,其中G可以为氢、卤素、或具有1至约4个碳原子的烷基基团,且R1可以选自具有1至约16个碳原子的烷基、环烷基、烯基、环烯基、烷芳基、芳烷基或芳基基团,其中任意基团可以视情况任选地被硅烷、硅、氧、卤素、羰基、羟基、酯、羧酸、脲、脲烷、碳酸根、胺、酰胺、硫、磺酸根、砜等取代或间断。
适用于本文的其它(甲基)丙烯酸酯包括多官能(甲基)丙烯酸酯单体例如二官能或三官能(甲基)丙烯酸酯如聚乙二醇二(甲基)丙烯酸酯、四氢呋喃(甲基)丙烯酸酯和二(甲基)丙烯酸酯、羟基丙基(甲基)丙烯酸酯("HPMA")、己二醇二(甲基)丙烯酸酯、三羟甲基丙烷三(甲基)丙烯酸酯(“TMPTMA”)、二乙二醇二甲基丙烯酸酯、三乙二醇二甲基丙烯酸酯(“TRIEGMA”)、四乙二醇二甲基丙烯酸酯、二丙二醇二甲基丙烯酸酯、二-(五亚甲基二醇)二甲基丙烯酸酯、四甘醇二丙烯酸酯、二甘油四甲基丙烯酸酯、四亚甲基二甲基丙烯酸酯、亚乙基二甲基丙烯酸酯、新戊二醇二丙烯酸酯、三羟甲基丙烷三丙烯酸酯和双酚-A单和二(甲基)丙烯酸酯例如乙氧基化的双酚-A(甲基)丙烯酸酯("EBIPMA")、和双酚-F单和二(甲基)丙烯酸酯例如乙氧基化的双酚-F(甲基)丙烯酸酯。
此外,还可以使用具有(甲基)丙烯酸酯官能团的聚丙烯酸酯。特别期望的是通过可控的还原聚合技术例如单电子转移活性自由基聚合技术制备的那些。参见美国专利第5,807,937号(Matyjaszawski)、美国专利申请公开第2010/0331493号(Percec)和美国专利申请公开第2011/0060157号(Glaser)。
本文中可以使用的另一个(甲基)丙烯酸酯硅酮(甲基)丙烯酸酯部分("SiMA"),例如美国专利第5,605,999号(Chu)中教导和要求保护的那些,此处明确地将其公开内容通过援引加入的方式纳入本文。
当然,也可以使用这些(甲基)丙烯酸酯的组合。
可固化的树脂组分在组合物中存在的量的范围应为约10重量%至约95重量%,期望地为约20重量%至约80重量%,例如约40重量%至约65重量%。
作为环氧树脂的固化剂,可以使用咪唑、双氰胺、羧酸、酐、酚硬化剂(phenolichardener)、胺、硫醇、醇和碱。
咪唑包括咪唑及其衍生物,例如异咪唑、咪唑、烷基取代的咪唑例如2-甲基咪唑、2-乙基-4-甲基咪唑、2,4-二甲基咪唑、丁基咪唑、2-十七碳烯基-4-甲基咪唑、2-甲基咪唑、2-十一碳烯基咪唑,1-乙烯基-2-甲基咪唑,2-n-十七烷基咪唑、2-十一烷基咪唑、2-十七烷基咪唑、2-苯基咪唑、2-乙基4-甲基咪唑、1-苄基-2-甲基咪唑、1-丙基-2-甲基咪唑、1-氰基乙基-2-甲基咪唑、1-氰基乙基-2-乙基-4-甲基咪唑、1-氰基乙基-2-十一烷基咪唑、1-氰基乙基-2-苯基咪唑、1-胍氨基乙基-2-甲基咪唑(1-guanaminoethyl-2-methylimidazole)和咪唑甲基咪唑的加成产物和咪唑和偏苯三酸的加成产物、2-正十七烷基-4-甲基咪唑等,通常,其中各烷基取代基包含最多至约17个碳原子且期望地包含最多至约6个碳原子;芳基取代的咪唑例如苯基咪唑、苄基咪唑、2-甲基-4,5-二苯基咪唑、2,3,5-三苯基咪唑、2-苯乙烯基咪唑、1-(十二烷基苄基)-2-甲基咪唑、2-(2-羟基-4-叔-丁基苯基)-4,5-二苯基咪唑、2-(2-甲氧基苯基)-4,5-二苯基咪唑、2-(3-羟基苯基)-4-,5-二苯基咪唑、2-(对二甲基氨基苯基)-4,5-二苯基咪唑、2-(2-羟基苯基)-4,5-二苯基咪唑、二(4,5-二苯基-2-咪唑)-苯-1,4、2-萘基-4,5-二苯基咪唑、1-苄基-2-甲基咪唑、2-对甲氧基苯乙烯基咪唑等,通常其中各芳基取代基包含最多至约10个碳原子且期望地包含最多至约8个碳原子。
作为用于自由基固化系统的固化剂,过氧化物为适合的选择。例如,可以使用氢过氧化物例如过氧化氢异丙苯(“CHP”)、过氧化氢对孟烷、叔丁基过氧化氢("TBH")和叔丁基过氧化苯甲酸。其他可用的过氧化物包括过氧化苯甲酰、过氧化二苯甲酰、1,3-双(叔丁基过氧异丙基)苯、过氧化二乙酰、丁基4,4-双(叔丁基过氧)戊酸酯、对氯过氧化苯甲酰、叔丁基过氧化异丙苯、二-叔丁基过氧化物、过氧化二异丙苯、2,5-二甲基-2,5-二-叔丁基过氧己烷、2,5-二甲基-2,5-二-叔丁基-过氧己-3-炔、4-甲基-2,2-二-叔丁基过氧戊烷及其组合。
固化剂存在的量的范围应为总组合物的约0.05重量%至约10重量%,期望地为约0.1重量%至约5重量%,例如约1重量%。
还可以使用无机填充剂组分,包括增强二氧化硅例如熔融二氧化硅,其可以为未经处理或经处理以改变其表面化学性质。然而,无机填充剂组分包括平均粒径分布在1-1000纳米("nm")范围内的颗粒。这样的填充剂颗粒的可商购的实例由Hans Chemie,Germany以商品名NANOPOX例如NANOPOX XP 22出售。NANOPOX填充剂为环氧树脂中的单分散二氧化硅填充剂分散体,含量为最高至约50重量%。通常,人们认为NANOPOX填充剂具有约5nm至约80nm的粒径。经报导NANOPOX XP 22在双酚-F环氧树脂的二缩水甘油基醚中包含40重量%的粒径为约15nm的二氧化硅颗粒。
Hans Chemie还以商品名称NANOPOX E生产材料。例如,报导Hans Chemie NANOPOXE品牌产品使得否则难以密封的电子组件能够完全浸渍,并且提供了大的机械性质和热性质的谱例如减少的收缩和热膨胀、断裂韧度和模量。在下表A中,Hans Chemie提供了关于提及的四种NANOPOX E产品的信息:
表A
1 3,4-环氧环己基甲基-3,4-环氧环己基碳酸酯
Hans Chemie报导通过使用NANOPOX E品牌产品可以显著地改善环氧配制物中的重要性质。例如:
·与常规的增强的填充剂相比较较低的配制物粘度
·无沉降
·断裂韧度、抗冲击性和模量增加
·耐刮性和耐磨性改善,收缩和热膨胀减小
·许多期望的性质例如热稳定性、化学耐性、玻璃转化温度、耐候性、介电性质改善,或至少无负面作用。
NANOPOX E与常规的填充剂例如石英的组合使得配制物的树脂含量降低,这意味着总填充剂含量可以增加至先前未获得的水平。
与各基础树脂相比较,可加工性基本上保持不变。
NANOPOX E用于其中期望或需要上述性质改善而不因过量提高的粘度而损害可加工性(由热解二氧化硅得知)的应用。应用实例为包封材料和涂料。重要的是强调NANOPOX E由于粒径小和无聚集体而导致的优异浸渍性质。这还使得否则难以密封的电子组件的完全浸渍成为可能。
根据制造商,NANOPOX E品牌产品为环氧树脂基质中的胶体硅溶胶。分散相由直径小于50nm且具有极窄的粒径分布的表面改性的球形SiO2纳米颗粒组成。这些大小仅为几纳米的球在树脂基质中分布,无聚集体。这导致SiO2含量最高至40重量%的分散体的极低的粘度。纳米颗粒由硅酸钠水溶液化学合成。
用作无机填充剂组分的其它期望的材料包括由以下构成或包含以下的那些:氧化铝、氮化硅、氮化铝、二氧化硅涂覆的氮化铝、氮化硼及其组合,当然,条件是颗粒具有1-1,000nm范围内的平均粒径分布。
无机填充剂组分的使用量应为组合物的约10至约80重量%,例如约12至约60重量%,期望地在约15至约35重量%范围内。
此外,可以使用助粘剂例如硅烷、缩水甘油基三甲氧基硅烷(可以商品名A-187商购自OSI)或γ-氨基丙基三乙氧基硅烷(可以商品名A-1100商购自OSI)。
常规添加剂也可以用于本发明的组合物中,以获得组合物、固化的反应产物、或两者的某些期望的物理性质。
热固性树脂组合物能够穿透入电路板和半导体设备之间的空间,并以此方式起底部填充胶的作用。这些本发明的组合物还显示降低的粘度,至少是在升高的温度条件下,并因此能够穿透入该空间。期望通过选择各成分的类型和比例以在25℃下达到5,000mPa·s或更低例如300至2,000mPa·s的粘度而制备热固性树脂组合物,以改善其穿透入电路板和半导体设备之间的空间(例如10至500μm)的能力。
参考图1,其示出了子组件例如CSP的实例,其中使用了本发明的热固性树脂组合物。
通过将半导体芯片2连接至载体基底(carrier substrate)1并适合地使用树脂3将其间的空间密封而形成半导体设备4。将此半导体设备固定在电路板5的预先确定的位置处,并通过适合的连接工具例如焊料将电极8和9电连接。为了改善可靠性,使用热固性树脂组合物的固化产物10密封载体基底1和电路板5之间的空间。热固性树脂组合物的固化产物10不需要完全填充载体基底1和电路板5之间的空间,但可以将其填充至能够缓解由热循环导致的应力的程度。
载体基底可以由以下构建:由A12O3、SiN3和莫来石(A12O3-SiO2)制成的陶瓷基底;由耐热树脂例如聚酰亚胺制成的基底或带;通常也被用做电路板的玻璃纤维增强的环氧树脂、ABS、和酚类基底;等。
对于倒装芯片部件,参考图2,其示出了其中半导体芯片已被固定于电路板上的倒装芯片部件,和使用热固性树脂组合物密封的底部填料(underfilling)。
通过将半导体芯片22连接至电路板21并适合地使用热固性树脂组合物23将其间的空间密封而形成倒装芯片部件24。将此半导体设备固定在电路板21的预先确定的位置处,并通过适合的电连接工具27和28例如焊料将电极25和26电连接。为了改善可靠性,使用热固性树脂组合物23密封半导体芯片22和电路板21之间的空间并随后固化。热固性树脂组合物的固化产物应完全填充该空间。
对于用于将半导体芯片电连接至载体基底的工具没有具体限制,且可以使用通过高熔点焊料或导电(或各向异性导电)胶、引线接合等的连接。为了促进连接,可以以隆起的形式形成电极。此外,为了改善连接的可靠性和持久性,可以使用适合的树脂密封半导体芯片和载体基底之间的空间。本发明中可以使用的半导体设备包括CSP、BGA、和LGA。
电路板可以由常规材料例如玻璃纤维增强的环氧树脂、ABS、苯并噁嗪、和酚醛树脂构建。
接下来,在固定过程中,将焊糊打印在电路板的需要的位置处,并适合地干燥以排出溶剂。随后,遵照图样将半导体设备固定至电路板上。使此电路板通过回流熔炉以使焊料熔化并由此焊接半导体设备。半导体设备和电路板之间的电连接不限于使用焊糊,而可以通过使用焊球实现。可选地,也可以通过导电胶或各向异性导电胶实现此连接。此外,可以在电路板上或半导体设备上施用或形成焊糊等。为了促进随后的修复,使用的焊料、导电胶或各向异性导电胶的选择应考虑其熔点、结合强度等。
在以此方式将半导体设备电连接至电路板之后,通常应对得到的结构进行连续性测试等。在通过这样的测试后,可以使用树脂组合物将半导体设备固定至其。以此方式,在失效的事件中,更容易在使用树脂组合物固定半导体设备之前将其移除。
随后,可以向半导体设备周围施用热固性树脂组合物。当将此组合物施用至半导体设备时,其通过毛细作用穿透入电路板和半导体设备的载体基底之间的空间。
通过施加热使热固性树脂组合物固化。在此加热的早期,热固性树脂组合物显示出粘度的显著降低,并因此显示出流动性增加,因此其更容易穿透入电路板和半导体设备之间的空间。此外,通过为电路板提供适合的通风孔,允许热固性树脂组合物完全地穿透入电路板和半导体设备之间的整个空间。
应调节施用的热固性树脂组合物的量,以几乎完全地填充电路板和半导体设备之间的空间。
热固性树脂组合物通常应通过在约100℃至约l50℃的温度下加热约5至约60分钟的一段时间而固化,例如在约110℃至约l30℃的温度下加热约15至约45分钟的一段时间。因此,可以使用相对低温和短时间的固化条件以获得极好的生产率。图1中所示的子组件可以以此方式构建。用于此目的的普通环氧基组合物例如仅基于双酚A型环氧树脂或双酚F型环氧树脂作为环氧树脂的那些组合物不具有相同的可获得的降解途径,而是仅在约300℃下开始分解。
将半导体设备如此固定在电路板上之后,可以对得到的子组件进行可操作性测试。在发现失效的事件中,可以以以下方式进行修复。
将已失效的半导体设备周围的区域在约170℃至约240℃的温度下局部地加热约10秒至约60秒范围内的一段时间,例如在约220℃的温度下加热30秒的一段时间。
一旦焊料熔化且树脂软化以导致结合强度降低,即将半导体设备拉开。
将半导体设备移除之后,热固性树脂组合物的固化的反应产物的残余物和焊料的残余物留在电路板上。可以简单地通过例如使用低摩擦布擦拭设备而移除热固性树脂组合物的固化的反应产物的残余物(参见图3)。过去,在残余物已通过以下而软化之后必须将经加工的反应产物刮除:将其加热至预先确定的温度,使用溶剂使其膨胀,或使用溶剂使其膨胀的同时将其加热至预先确定的温度(参见图3)。
最后,可以以与上述方式相同的方式再次在已被清洁的电路板上固定新的半导体设备。由此,完成对失效的部位的修复。
当在电路板上发现失效时,如果期望,可以通过以与上述方式相同的方式将半导体设备的底部上留下的热固性树脂组合物的固化的反应产物的残余物和焊料的残余物移除而重新使用半导体设备。
尽管本发明的组合物已被描述为可主要用作底部填充胶,但还考虑到本发明的组合物可以用于液压成型应用中作为结构粘合剂(例如在如智能手机和平板的手持显示设备的构建中)、用于半导体封装的膜、用于无源电子组件的短/长期密封剂、和涂料。
将通过以下非限制性实施例进一步解释本发明。
实施例
合成
实施例1
将DCPD的二羧酸(“DCPD二酸”)(50g,227mmol)以及DMSO(300mL)置于配有机械搅拌器和滴液漏斗(addition funnel)的1L 4颈烧瓶中。在5分钟的时间段内缓慢地添加KOH(26.8g)在30mL水中的溶液,并继续搅拌,持续另外的15分钟。随后使用油浴在50℃的温度下加热反应混合物。在2小时的一段时间内滴加在25mL DMSO中的表溴醇(epibromohydrin)(124.4g,908mmol)并继续搅拌,持续额外的6小时。
将反应混合物用600mL乙酸乙酯萃取,用NaHCO3水溶液洗涤,用水洗涤若干次,随后用无水MgSO4干燥。蒸发溶剂以获得棕色液体,随后将其用50mL甲苯稀释,并蒸馏以获得DCPD二酸的二缩水甘油基酯(“DCPD环氧化物”)(60g,80%产率)。
实施例2
将DCPD二酸(15.2g,69mmol)和间苯二酚二缩水甘油基醚(30.7g,138mmol)在THF(450mL)中的混合物置于配有氮气入口和机械搅拌器的1L 4颈烧瓶中。搅拌30分钟的一段时间之后,添加催化量的四丁基碘化铵(1.27g,3.44mmol),将混合物加热至回流,持续36小时的一段时间。进行红外(“IR”)光谱分析,其结果表明与DCPD二酸不同的1707cm-1处的羰基带的出现。
将反应混合物冷却至室温之后,蒸发THF并将600mL乙酸乙酯添加至残余物中。将有机层用水洗涤若干次,用饱和的NaHCO3水溶液洗涤,随后再次用水洗涤。用无水MgSO4干燥后,蒸发溶剂以获得深棕色粘性液体状的以上所示的DCPD链延长的环氧化物(35g,78%产率)。
DCPD链延长的环氧化物的IR光谱分析显示1707cm-1处的羰基带。
实施例3
将DCPD环氧化物(2.06g,6.2mmol)、甲基丙烯酸(0.54g,6.2mmol)、四丁基碘化铵(100mg)和叔丁基儿茶酚(30mg)与THF(20mL)一起置于圆底烧瓶中,并在回流下混合5小时的一段时间。将反应混合物冷却至室温之后,添加乙酸乙酯,并将有机层用饱和的NaHCO3水溶液洗涤两次、用K2CO3水溶液洗涤并用无水MgSO4干燥。随后蒸发溶剂以获得粘性的深棕色液体状的DCPD混合环氧化物-甲基丙烯酸酯(1.82g,70%收率)。
实施例4
将DCPD二酸(35.7g,162mmol)在THF(300mL)中的混合物置于配有氮气入口的500mL 4颈烧瓶中。将混合物使用冰-盐浴冷却并在5分钟的一段时间内滴加草酰氯(61.7g,486mmol)。使反应混合物达到室温,并搅拌额外的4小时。蒸发溶剂和过量的草酰氯,在氮气氛下将残余物溶于THF(200mL)中,并用冰冷却溶液。在搅拌下添加三乙胺(41g,405mmol),随后在30分钟的一段时间内添加HEMA(42.2g,324mmol),并在搅拌下添加叔丁基儿茶酚(140mg)。约4h后,蒸发THF并将反应混合物用乙酸乙酯(400mL)萃取、用水洗涤4次并用无水MgSO4干燥。蒸发溶剂,以获得深棕色液体状的DCPD二甲基丙烯酸酯(57g,73%收率),其通过柱色谱法纯化。
实施例5
将DCPD二酸(29g,132mmol)溶于DMF中;在搅拌下添加K2CO3(36g,263mmol),所述搅拌持续30分钟。随后在10分钟的一段时间内逐份添加烯丙基溴(42g,347mmol)。在室温下将反应混合物搅拌过夜。随后将反应混合物用乙酸乙酯(500ml)萃取,用水洗涤4次,并用无水MgSO4干燥。蒸发溶剂以获得DCPD二酸的二烯丙基酯(31g,78%收率)。
实施例6
在搅拌下将DCPD二酸(4.5g,20.4mmol)、DMSO(100mL)、和K2CO3(3.39g,24.5mmol)置于配有磁力搅拌棒的250mL烧瓶中,所述搅拌持续15分钟的一段时间。添加4-乙烯基苄基氯(7.2g,47.2mmol)并在室温下将反应混合物搅拌过夜。
IR光谱分析显示1709cm-1处的酯的羰基带。
将反应混合物用乙酸乙酯萃取,用水洗涤若干次并用无水MgSO4干燥。蒸发溶剂并通过柱色谱法纯化反应混合物,以获得黄色油状的DCPD二酸的二苯乙烯(distyrenic)衍生物(5.3g,58%收率)。
实施例7
将环戊二烯基钠(sodium cyclopentadienylide)在THF中的2M溶液(30ml,60mmol)置于配有氮气入口和磁力搅拌棒的250mL 3颈烧瓶中的THF(50mL)中。将悬浮液在冰中冷却约30分钟的一段时间,之后在约30分钟的一段时间内滴加(2-溴乙氧基)-叔-丁基二甲基硅烷(14.34g,60mmol)的溶液。将混合物在相同的温度下搅拌约2小时的一段时间,随后在室温下搅拌过夜。蒸发THF,将产物用乙酸乙酯(200mL)萃取、用水洗涤并用无水MgSO4干燥。蒸发溶剂以得到中间体粗2-羟基乙基环戊二烯的甲硅烷基衍生物,将其通过在约110℃的温度下加热约1.5小时的一段时间而二聚,以提供中间体DCPD二乙醇的甲硅烷基衍生物。
向此粗产物在THF(50mL)中的溶液添加TBAF在THF中的1M溶液(60mL,60mmol),并将混合物在室温下搅拌过夜。蒸发THF,并将产物用乙酸乙酯(200ml)萃取、用水洗涤并用无水MgSO4干燥。溶剂蒸发提供棕色油状的DCPD二乙醇(8.1g,61%收率)。
实施例8
将双羟基乙基DCPD(1.05g,4.8mmol)在CH2Cl2(25mL)中的混合物置于配有氮气入口和磁力搅拌棒的3颈100mL烧瓶中。添加三乙胺(2.41g,23.8mmol)和催化量的DMAP(50mg)。将生成的混合物用冰冷却,并滴加甲基丙烯酸酐(2.94g,19.1mmol)。在相同的温度下搅拌约30分钟的一段时间并随后在室温下搅拌额外的约3小时的一段时间之后,添加NaHCO3水溶液(30mL)。随后蒸发CH2Cl2,并将产物用乙酸乙酯萃取。将有机层用水洗涤并用无水MgSO4干燥。添加叔丁基儿茶酚(200ppm)并蒸发溶剂,以提供DCPD二乙醇的二甲基丙烯酸酯(1.4g,82%收率)。
实施例9
将NaH(2.18g,油中60%的分散体,54.4mmol)在无水DMF(25mL)中的溶液添加至配有氮气入口和磁力搅拌棒的100mL 3颈烧瓶中。将溶液在冰浴中冷却,并在约15分钟的一段时间内缓慢地添加双羟基乙基DCPD(3g,13.6mmol)在无水DMF(25mL)中的溶液。在搅拌额外的约30分钟的一段时间之后,缓慢地滴加表溴醇(7.47g,54.4mmol)。将混合物温热至室温,并搅拌过夜,其后添加异丙醇,随后添加甲苯(200ml)。将有机层用水洗涤若干次,并用无水MgSO4干燥,之后蒸发溶剂。通过柱色谱法纯化粗反应产物,以分离二缩水甘油基醚(2.3g,51%收率)。
热固性树脂组合物
可以由如下表1中所述的组分制备热固性树脂组合物,其中各样品包含少于1重量%的消泡剂和硅烷助粘剂。
表1
1 EPOTOHTO YD-8125,可商购自Tohto Kasei
2 EPOTOHTO ZX-1059,可商购自Tohto Kasei
3 化合物A
4 DENACOL EX-146,对-叔丁基苯基缩水甘油基醚,可商购自Nagase ChemtexCorporation
5 可商购自AlzChem LLC
6 可商购自Asahi Kasei Chemicals Corporation
表2
1 SR833-S,三环癸烷二甲醇二丙烯酸酯,可商购自Sartomer,Inc.
2 SR423-A,甲基丙烯酸异冰片酯,可商购自Sartomer,Inc.
3 TRIGONOX 21s,叔-丁基过氧-2-乙基己酸酯,可商购自Akzo Nobel PolymerChemicals LLC
4 EPICLON 830-CRP,双酚F,可商购自Dainippon Ink and Chemicals,Inc.
5 EPICLON HP-4032D,1,6-双(2,3-环氧基丙氧基)萘,可商购自Dainippon Inkand Chemicals Inc.
表3
1 EPOTOHTO YD-8125,可商购自Tohto Kasei
2 EPOTOHTO ZX-1059,可商购自Tohto Kasei
3 化合物H
4 DENACOL EX-146,对-叔丁基苯基缩水甘油基醚,可商购自Dainippon Ink andChemicals Inc.
表4
1 EPOTOHTO YD-8125,可商购自Tohto Kasei
2 EPOTOHTO ZX-1059,可商购自Tohto Kasei
3 化合物A
4 DENACOL EX-146,对-叔丁基苯基缩水甘油基醚,可商购自Dainippon Ink andChemicals Inc.
将可商购自Henkel Electronic Materials,LLC,Irvine,California的HYSOL UF3808和HYSOL UF 3800用于比较目的,并简单地以产品名提及。
物理性质
在未固化的状态下,将各样品在约25℃的分配温度下由注射器或喷射分配器分配在6x 6mm晶片级CSP(“WL-CSP”)旁边。在少于30秒内,使样品通过毛细作用流入WL-CSP和与样品连接的电路板之间的底部填充空间。
通过暴露于约100℃至约150℃范围的升高的温度条件(持续约10至约六十(60)分钟的一段时间)使样品固化。
参见下表5-7,其示出固化的组合物样品A-K的动态力学分析数据。
表5
图4示出了表5中提及的各样品的模量随温度的变化。
表6
图5示出了表6中提及的各样品的模量随温度的变化。
表7
图10示出了表7中提及的各样品的角正切随温度的变化。
热循环测试
参考下表8,其给出了由对获自缓变率(ramp rate)为3℃/分钟的四个-85℃至250℃至-85℃的循环的热循环结果进行动态力学分析而得到的模量值。
表8
参考图6-8,其示出了表8中所示的样品;图9示出了HYSOL UF 3808的模量随温度变化的轨迹。
计算样品在循环1和循环4期间的tanδ的峰值(玻璃化转变温度或Tg)之间的差,Δtanδ。还计算了25℃下样品在循环1和循环4期间的模量之间的差。对于样品K、L、和M,观察到各Tg均降低;HYSOL UF 3800和HYSOL UF 3808观察到的相反。观察到的样品K、L、和M的模量降低比HYSOL UF 3800和HYSOL UF 3808显著得多。
参考下表9,其示出了与可商购的产品HYSOL UF 3800和HYSOL UF 3808比较的两种样品的另外的热循环评价。一个热循环条件(热循环1)在-40℃至85℃的温度下进行,每循环30分钟;另一个热循环(热循环2)在-55℃至125℃的温度下进行,每循环30分钟。使用的组件为6x 6mm WL-CSP。
表9
再加工
使用热空气发生器,通过在285℃的温度下施用热空气30秒的一段时间而加热用样品固定于电路板的WL-CSP周围的区域。随后,借由适合的喷嘴提升WL-CSP而通过真空抽吸来移除WL-CSP。通过擦拭表面而将任何残留的固化的反应产物残余物从板上清洁。参考图3,其示出了此过程的流程图。
Claims (13)
1.可固化的组合物,当暴露于高于用于固化所述组合物的温度条件的温度条件时,其反应产物可以可控地降解,所述可固化的组合物包含:
(a)可固化的树脂组分;
(b)固化剂;和
(c)用至少两个羧酸基团官能化的二烯/亲二烯体偶合物,其中所述二烯/亲二烯体偶合物为式I的化合物:
其中X为C=O;Y为O;A为亚烷基;Z为H;n为0或1;且m为2-4。
2.电子设备,其包括半导体设备和与所述半导体设备电连接的电路板,或半导体芯片和与所述半导体芯片电连接的电路板,其使用如权利要求1所述的可固化的组合物分别作为所述半导体设备与所述电路板之间的或所述半导体芯片与所述电路板之间的底部填充胶进行组装,其中所述组合物的反应产物能够在暴露于超过用于固化所述组合物的温度条件的温度条件下软化和失去其粘合性。
3.密封底部填料的方法,所述底部填料位于包括固定于载体基底上的半导体芯片的半导体设备和与所述半导体设备电连接的电路板之间或位于半导体芯片和与所述半导体芯片电连接的电路板之间,其步骤包括:
(a)将如权利要求1所述的组合物分配入位于所述半导体设备和所述电路板之间的或位于所述半导体芯片和所述电路板之间的所述底部填料中;和
(b)将如此分配的组合物暴露于100℃至150℃,持续10分钟至一小时的时间,以使得所述组合物形成反应产物。
4.可固化的组合物,当暴露于高于用于固化所述组合物的温度条件的温度条件时,其反应产物可以可控地降解,所述可固化的组合物包含:
(a)可固化的树脂组分;
(b)固化剂;和
(c)用至少两个对所述可固化的树脂组分具有反应性的基团官能化的二烯/亲二烯体偶合物,其中所述二烯/亲二烯体偶合物为式II的化合物:
其中X1和X2各自为C=O;Y1和Y2各自为O;A1和A2各自为亚烷基;Z1和Z2相同或不同且各自独立地选自H、(甲基)丙烯酰基、缩水甘油基、环氧基或(甲基)丙烯酸酯基;且n1和n2各自为0。
5.如权利要求1或4所述的组合物,其中所述可固化的树脂组分选自环氧树脂、环硫化物、氧杂环丁烷、硫代氧杂环丁烷、噁嗪、马来酰亚胺、衣康酰胺、纳迪酰亚胺、(甲基)丙烯酸酯、(甲基)丙烯酰胺、及它们的组合。
6.如权利要求1所述的组合物,其中所述的两个羧酸基团相同。
7.如权利要求1所述的组合物,其中所述的两个羧酸基团不同。
8.如权利要求4所述的组合物,其中所述的两个反应性基团相同。
9.如权利要求4所述的组合物,其中所述的两个反应性基团不同。
10.如权利要求1或4所述的组合物,其中所述固化剂选自咪唑、双氰胺、羧酸、酐、酚硬化剂、胺、硫醇、醇、和碱。
11.如权利要求1所述的组合物,其中所述高于用于固化所述组合物的温度条件的温度条件为170℃或更高。
12.如权利要求1所述的组合物,其中所述用于固化所述组合物的温度条件为100℃至150℃。
13.可固化的组合物,当暴露于高于用于固化所述组合物的温度条件的温度条件时,其反应产物降解,所述可固化的组合物包含:
(a)可固化的树脂组分;
(b)固化剂;和
(c)用至少两个对所述可固化的树脂组分具有反应性的基团官能化的二烯/亲二烯体偶合物,
其中所述二烯/亲二烯体偶合物中的所述二烯选自无环的1,3-二烯、环戊二烯、环己二烯、富烯、吡咯、萘和蒽,所述二烯/亲二烯体偶合物中的所述亲二烯体基于选自以下的物质:环戊二烯、马来酰亚胺、异马来酰亚胺、柠康酰亚胺、衣康酰亚胺、马来酸酯、巴豆酸酯、肉桂酸酯、富马酸酯、(甲基)丙烯酸酯、氰基丙烯酸酯、苯醌、苯醌肟、苯醌亚胺、萘醌、亚烷基丙二酸酯、(甲基)丙烯酰胺、和含吸电子基团的炔。
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US20180155588A1 (en) | 2018-06-07 |
JP2016514738A (ja) | 2016-05-23 |
EP2976380B1 (en) | 2018-10-10 |
US10472548B2 (en) | 2019-11-12 |
WO2014153513A1 (en) | 2014-09-25 |
US9938437B2 (en) | 2018-04-10 |
CN105073846A (zh) | 2015-11-18 |
JP6596412B2 (ja) | 2019-10-23 |
US20160002510A1 (en) | 2016-01-07 |
EP2976380A4 (en) | 2016-11-02 |
EP2976380A1 (en) | 2016-01-27 |
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