CN112004845B - 树脂组合物、层叠体、带树脂组合物层的半导体晶圆、基板和半导体装置 - Google Patents
树脂组合物、层叠体、带树脂组合物层的半导体晶圆、基板和半导体装置 Download PDFInfo
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- CN112004845B CN112004845B CN201980027899.7A CN201980027899A CN112004845B CN 112004845 B CN112004845 B CN 112004845B CN 201980027899 A CN201980027899 A CN 201980027899A CN 112004845 B CN112004845 B CN 112004845B
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Abstract
提供:具有优异的助焊剂活性、挠性和保存稳定性的适合于预施底部填充材料用的树脂组合物。本发明的树脂组合物含有:具有酚性羟基的化合物(A)、金属离子捕捉剂(B)和自由基聚合性化合物(C)。
Description
技术领域
本发明涉及树脂组合物、使用树脂组合物的层叠体、带树脂组合物层的半导体晶圆、带树脂组合物层的半导体搭载用基板和半导体装置。详细而言,本发明涉及作为底部填充材料有用的树脂组合物。
背景技术
近年来,随着半导体装置的小型化和高性能化,作为将半导体芯片(以下,有时简称为“芯片”)搭载于半导体搭载用基板(以下,有时简称为“基板”)的方法,倒装芯片安装备受关注。倒装芯片安装中,一般有如下工艺:将芯片与基板接合后,在芯片与基板的间隙填充底部填充材料,并使其固化。然而,随着半导体装置的小型化和高性能化,在芯片上排列的电极的窄间距化和电极间的窄间隙化推进,底部填充材料填充的长时间化所导致的作业性的恶化和未填充等填充不良的发生成为问题。针对于此,研究了如下工艺:向芯片或基板供给预施底部填充材料后,同时进行芯片与基板的接合、以及底部填充材料的填充。
将芯片与基板借助容易被氧化的金属、例如焊料、铜进行接合的情况下,为了将成为阻碍接合因素的金属氧化膜从接合部去除从而得到良好的金属接合,有时在预施底部填充材料中添加源自羧酸等的助焊剂成分。
专利文献1中记载了一种使用环氧化合物的预施底部填充材料。另外,专利文献2中也记载了一种使用环氧化合物的预施底部填充材料。
专利文献3中记载了一种使用环氧化合物和助焊剂成分的预施底部填充材料。另外,专利文献4中记载了一种使用丙烯酸类单体的底部填充材料。而且,专利文献5中记载了一种使用自由基聚合性单体的预施底部填充材料。
专利文献6中有关于薄膜状粘接剂的记载,所述薄膜状粘接剂具备含有具有能跟铜离子络合的骨架的树脂的铜离子吸附层,具有能跟铜离子络合的骨架的树脂为具有三嗪骨架的酚醛树脂。
现有技术文献
专利文献
专利文献1:日本特开2008-133423号公报
专利文献2:日本特开2016-027174号公报
专利文献3:日本特开2013-112730号公报
专利文献4:日本特开2015-172145号公报
专利文献5:日本特表2015-503220号公报
专利文献6:日本特开2011-52109号公报
发明内容
发明要解决的问题
专利文献1和2中记载的使用环氧化合物的预施底部填充材料的情况下,有环氧化合物与各种材料的粘接性高、电绝缘性优异的优点。然而,这样的预施底部填充材料有意不包含助焊剂成分。由此,对于专利文献1和2中记载的预施底部填充材料,难以去除接合部的氧化膜。
另外,专利文献3中,使用特定的含羧基的化合物作为助焊剂成分。然而,含羧基的化合物与环氧化合物在室温下也会轻微进行反应,保管中助焊剂活性经时地降低,因此,存在接合稳定性低、缺乏量产性的缺点。
专利文献4中,也有意不包含助焊剂成分,因此,无法在金属接合前去除接合部的氧化膜。
专利文献5中,使用热自由基引发剂作为自由基聚合性单体的聚合引发剂。然而,专利文献5中,使用含有羧基的聚合物,但分子量大,因此,羧基的运动性低,无法期待充分的助焊剂活性。
另外,铜具有容易腐蚀的特性,结果由于腐蚀而产生的铜离子渗透至半导体芯片内,作用于晶体管,从而引起误操作,有在芯片的电极间容易引起迁移所导致的短路的倾向。因此,专利文献6中,有关于含有具有能跟铜离子络合的骨架即三嗪骨架的酚醛树脂的薄膜状粘接剂的记载。然而,对于该粘接剂,具有三嗪骨架的酚成分被掺入树脂骨架中,因此,具有运动性低、接合部的金属氧化膜去除性极低的问题。
本发明是鉴于这样的课题而作出的,提供:具有优异的助焊剂活性、挠性和保存稳定性、适合于底部填充材料用的树脂组合物、层叠体、带树脂组合物层的半导体晶圆、带树脂组合物层的半导体搭载用基板、和半导体装置。
用于解决问题的方案
本发明人等为了解决前述问题而进行了深入研究,结果发现:含有具有酚性羟基的化合物(A)、金属离子捕捉剂(B)、和自由基聚合性化合物(C) 的树脂组合物可以解决前述课题,完成了本发明。
即,本发明包含以下的内容。
[1]一种树脂组合物,其含有:
具有酚性羟基的化合物(A)、
金属离子捕捉剂(B)、和
自由基聚合性化合物(C)。
[2]根据[1]所述的树脂组合物,其中,前述具有酚性羟基的化合物(A) 的分子量为200以上、且熔点为300℃以下。
[3]根据[1]或[2]所述的树脂组合物,其中,前述具有酚性羟基的化合物 (A)的5%质量减少温度为250℃以上。
[4]根据[1]~[3]中任一项所述的树脂组合物,其中,前述金属离子捕捉剂 (B)含有选自氮和氧中的至少1种元素作为配位原子。
[5]根据[1]~[4]中任一项所述的树脂组合物,其中,前述金属离子捕捉剂 (B)含有选自由胺类、胺衍生物、醚衍生物和酮衍生物组成的组中的至少1 种。
[6]根据[1]~[5]中任一项所述的树脂组合物,其中,前述金属离子捕捉剂 (B)含有选自由三嗪衍生物、联吡啶衍生物和二酮衍生物组成的组中的至少1种。
[7]根据[1]~[6]中任一项所述的树脂组合物,其中,前述金属离子捕捉剂 (B)含有1,3-二酮。
[8]根据[1]~[6]中任一项所述的树脂组合物,其中,前述金属离子捕捉剂 (B)含有选自由2,4-二氨基-6-甲基-1,3,5-三嗪、2,2’-联吡啶、1,3-二苯基-1,3- 丙二酮、1-(2-均三甲苯)-1,3-丁二酮、1,3-双(4-甲氧基苯基)-1,3-丙二酮、 1-(4-叔丁基苯基)-3-(4-甲氧基苯基)-1,3-丙二酮、和(E,E)-1,7-双(4- 羟基-3-甲氧基苯基)-1,6-庚二烯-3,5-二酮组成的组中的至少1种。
[9]根据[1]~[8]中任一项所述的树脂组合物,其中,前述金属离子捕捉剂 (B)含有选自由1-(4-叔丁基苯基)-3-(4-甲氧基苯基)-1,3-丙二酮、和(E,E) -1,7-双(4-羟基-3-甲氧基苯基)-1,6-庚二烯-3,5-二酮组成的组中的至少1种。
[10]根据[1]~[9]中任一项所述的树脂组合物,其中,前述自由基聚合性化合物(C)含有选自由(甲基)丙烯酸酯化合物、马来酰亚胺化合物、和丙烯基化合物组成的组中的至少1种。
[11]根据[10]所述的树脂组合物,其中,前述自由基聚合性化合物(C) 含有选自由2,2’-双{4-(4-马来酰亚胺苯氧基)苯基}丙烷、1,2-双(马来酰亚胺)乙烷、1,4-双(马来酰亚胺)丁烷、1,6-双(马来酰亚胺)己烷、N,N’-1,3- 亚苯基双马来酰亚胺、N,N’-1,4-亚苯基双马来酰亚胺、N-苯基马来酰亚胺、下述式(1)所示的马来酰亚胺化合物、下述式(2)所示的马来酰亚胺化合物和下述式(3)所示的马来酰亚胺化合物组成的组中的至少1种。
(式(1)中,R1各自独立地表示氢原子或甲基,n1表示1以上的整数。)
(式(2)中,n2的平均值为1以上且30以下。)
(式(3)中,R2各自独立地表示氢原子、甲基或乙基,R3各自独立地表示氢原子或甲基。)
[12]根据[11]所述的树脂组合物,其中,前述自由基聚合性化合物(C) 含有选自由2,2’-双{4-(4-马来酰亚胺苯氧基)苯基}丙烷、前述式(1)所示的马来酰亚胺化合物、前述式(2)所示的马来酰亚胺化合物和前述式(3) 所示的马来酰亚胺化合物组成的组中的至少1种马来酰亚胺化合物。
[13]根据[1]~[12]中任一项所述的树脂组合物,其中,前述树脂组合物中的前述具有酚性羟基的化合物(A)的含量相对于前述树脂组合物中的前述自由基聚合性化合物(C)的总计量100质量份为5质量份以上且50质量份以下。
[14]根据[1]~[13]中任一项所述的树脂组合物,其中,前述树脂组合物中的前述金属离子捕捉剂(B)的含量相对于前述树脂组合物中的前述自由基聚合性化合物(C)的总计量100质量份为5质量份以上且50质量份以下。
[15]根据[1]~[14]中任一项所述的树脂组合物,其还含有无机填充材料 (D)。
[16]根据[15]所述的树脂组合物,其中,前述无机填充材料(D)具有电绝缘性。
[17]根据[15]或[16]所述的树脂组合物,其中,前述无机填充材料(D) 的平均粒径为3μm以下。
[18]根据[15]~[17]中任一项所述的树脂组合物,其中,前述无机填充材料(D)含有选自由二氧化硅、氢氧化铝、氧化铝、勃姆石、氮化硼、氮化铝、氧化镁和氢氧化镁组成的组中的至少1种。
[19]根据[15]~[18]中任一项所述的树脂组合物,其中,前述树脂组合物中的前述无机填充材料(D)的含量相对于前述自由基聚合性化合物(C) 的总计量100质量份为300质量份以下。
[20]根据[1]~[19]中任一项所述的树脂组合物,其还含有挠性赋予成分 (E)。
[21]根据[20]所述的树脂组合物,其中,前述挠性赋予成分(E)含有热塑性的高分子化合物,前述高分子化合物的质均分子量为1000以上且 1000000以下。
[22]根据[20]或[21]所述的树脂组合物,其中,前述挠性赋予成分(E) 含有选自由(甲基)丙烯酸类低聚物和(甲基)丙烯酸类聚合物组成的组中的至少1种。
[23]根据[1]~[22]中任一项所述的树脂组合物,其用于预施底部填充材料。
[24]一种层叠体,其具备:
支撑基材;和,
层叠于前述支撑基材上的含有[1]~[23]中任一项所述的树脂组合物的层。
[25]一种带树脂组合物层的半导体晶圆,其具备:
半导体晶圆;和,
层叠于前述半导体晶圆的[24]所述的层叠体,
含有前述树脂组合物的层层叠于前述半导体晶圆。
[26]一种带树脂组合物层的半导体搭载用基板,其具备:
半导体搭载用基板;和,
层叠于前述半导体搭载用基板的[24]所述的层叠体,
含有前述树脂组合物的层层叠于前述半导体搭载用基板。
[27]一种半导体装置,其具备[25]所述的带树脂组合物层的半导体晶圆和/或[26]所述的带树脂组合物层的半导体搭载用基板。
发明的效果
根据本发明,可以提供:具有优异的助焊剂活性、挠性和保存稳定性、适合于底部填充材料用的树脂组合物、层叠体、带树脂组合物层的半导体晶圆、带树脂组合物层的半导体搭载用基板、和半导体装置。
具体实施方式
以下,对用于实施本发明的方式(以下,简称为“本实施方式”)详细地进行说明。需要说明的是,以下的本实施方式为用于说明本发明的示例,本发明不仅限定于本实施方式。
本说明书中的“(甲基)丙烯酰基”是指,“丙烯酰基”和对应于其的“甲基丙烯酰基”这两者。“(甲基)丙烯酸”是指,“丙烯酸”和对应于其的“甲基丙烯酸”这两者。“(甲基)丙烯酸酯”是指,“丙烯酸酯”和对应于其的“甲基丙烯酸酯”这两者。
本实施方式的一方案的树脂组合物含有:具有酚性羟基的化合物(A)、金属离子捕捉剂(B)、和自由基聚合性化合物(C)。本实施方式的树脂组合物优选用于底部填充材料的用途,更优选用于预施底部填充材料的用途。
本实施方式的另一方案的树脂组合物在前述各成分的基础上,还含有无机填充材料(D)。
本实施方式的另一方案的树脂组合物在前述各成分的基础上,还含有挠性赋予成分(E)。
本实施方式的另一方案还提供:使用本实施方式的树脂组合物得到的层叠体(以下,也称为“树脂层叠体”)、使用层叠体制作的带树脂组合物层的半导体晶圆、使用层叠体制作的带树脂组合物层的半导体搭载用基板、和使用本实施方式的树脂组合物制作的半导体装置。
〔I.树脂组合物〕
本实施方式的树脂组合物为适合作为用于芯片的倒装芯片安装的底部填充材料使用的树脂组合物。该树脂组合物含有:具有酚性羟基的化合物(A)、金属离子捕捉剂(B)、和自由基聚合性化合物(C)。本实施方式的树脂组合物可以还包含无机填充材料(D)和/或挠性赋予成分(E)。
〔I-1.具有酚性羟基的化合物(A)〕
具有酚性羟基的化合物(A)为主要有利于树脂组合物的助焊剂活性的成分。
作为具有酚性羟基的化合物(A),只要为在分子中具有1个以上酚性羟基的化合物就没有特别限定。作为化合物(A),可以为酚醛树脂。
对于具有酚性羟基的化合物(A),优选防止在倒装芯片安装中在体现助焊剂活性前挥发,即,防止在去除接合部的氧化膜前具有酚性羟基的化合物 (A)挥发。从这样的观点出发,具有酚性羟基的化合物(A)的分子量只要发挥本实施方式的效果就没有特别限定,优选200以上,从降低热固化时的挥发成分的观点出发,更优选250以上,从降低倒装芯片接合中的挥发成分的观点出发,进一步优选300以上。另一方面,从具有作为酸的运动性、得到更充分的助焊剂活性的观点出发,具有酚性羟基的化合物(A)的分子量优选10000以下,从溶剂溶解性的观点出发,更优选8000以下,从确保在倒装芯片接合中用于效率良好地到达接合部的金属氧化膜的运动性的观点出发,进一步优选6000以下。
需要说明的是,本实施方式中,关于分子量,为化合物的情况下,表示其化合物的分子量,为树脂的情况下,表示质均分子量(Mw)。质均分子量可以利用GPC(凝胶渗透色谱)法将聚苯乙烯作为标准物质而求出。
具有酚性羟基的化合物(A)的熔点只要发挥本实施方式的效果就没有特别限定,优选300℃以下,从在一般的焊料的熔点以下熔融作用于金属氧化膜的观点出发,更优选0~260℃,从确保室温下的保存稳定性、且需要在倒装芯片接合时用于接合的焊料的熔点以下进行熔融的观点出发,进一步优选40~240℃。
具有酚性羟基的化合物(A)的5%质量减少温度只要发挥本实施方式的效果就没有特别限定,优选250℃以上,从抑制半导体装置制造工艺中的加热时的挥发成分的观点出发,更优选260℃以上,出于抑制倒装芯片接合时的挥发成分的理由,进一步优选270℃以上。5%质量减少温度如果低于250℃,则倒装芯片接合时的挥发成分大量发生,有成为固化物中的空隙、工序污染的原因的担心。
具有酚性羟基的化合物(A)的5%质量减少温度可以利用热重分析(TGA) 而测定。对测定方法具体地进行说明。在TGA中投入规定量的化合物,以10℃ /分钟从室温升温至500℃。将由得到的质量减少曲线中质量减少5%的温度作为5%质量减少温度。
作为具有酚性羟基的化合物(A),例如可以举出9,9’-双-(4-羟基-3-甲基苯基)芴、双甲酚芴、双酚芴、2,4,6-三(3,5-二-叔丁基-4-羟基苄基)均三甲苯、橙皮苷、α,α’,α”-三(4-羟基苯基)-1-乙基-4-异丙基苯、α,α’-双(4- 羟基-3,5-二甲基苯基)-1,4-二异丙基苯、4,4’-亚甲基双(2,6-二-叔丁基苯酚)、 1,1’,3-三(2,5-二甲基-4-羟基苯基)-3-苯基丙烷、4,4’-[1-[4-[1-[4-羟基苯基]-1- 甲基乙基]苯基]乙叉基]双酚、2,3,4-三羟基二苯甲酮、2,3,4,4’-四羟基二苯甲酮、2-双(4-羟基苯基)丙烷、三(4-羟基苯基)甲烷、1,1’,1”-三(4-羟基 -3-甲基苯基)乙烷、1,1’,2,2’-四(4-羟基苯基)乙烷、4,4’-丁叉基双(6-叔丁基-间甲酚)、季戊四醇四[3-(3,5-二-叔丁基-4-羟基苯基)丙酸酯]。
另外,作为属于具有酚性羟基的化合物(A)的酚醛树脂,例如还可以举出双酚A型酚醛树脂、双酚E型酚醛树脂、双酚F型酚醛树脂、双酚S型酚醛树脂、苯酚酚醛清漆树脂、双酚A酚醛清漆型酚醛树脂、缩水甘油酯型酚醛树脂、芳烷基酚醛清漆型酚醛树脂、联苯芳烷基型酚醛树脂、甲酚酚醛清漆型酚醛树脂、多官能酚醛树脂、萘酚树脂、萘酚酚醛清漆树脂、多官能萘酚树脂、蒽型酚醛树脂、萘骨架改性酚醛清漆型酚醛树脂、苯酚芳烷基型酚醛树脂、萘酚芳烷基型酚醛树脂、二环戊二烯型酚醛树脂、联苯型酚醛树脂、脂环式酚醛树脂、多元醇型酚醛树脂、含磷酚醛树脂、含羟基的有机硅树脂类、丙烯基酚醛树脂、烯丙基酚醛树脂、丙烯基亚联苯基树脂。
具有酚性羟基的化合物(A)也可以使用市售的产品,例如可以举出DIC 株式会社制PHENOLITE(注册商标)KA-1163、田冈化学工业株式会社制 TBIS(注册商标)-MP、新日铁化学株式会社制SN-495V、群荣化学工业株式会社制LVA01、群荣化学工业株式会社制BPN01、群荣化学工业株式会社制TPMP01、群荣化学工业株式会社制PPN-80、群荣化学工业株式会社制 ELPC75、Fudow Co.,Ltd.制GP-100、日本化药株式会社制GPH103。
将本实施方式的树脂组合物用作底部填充材料、优选用作预施底部填充材料的半导体装置中,从挥发成分的抑制和分子的运动性的观点出发,在这些具有酚性羟基的化合物(A)中优选9,9’-双-(4-羟基-3-甲基苯基)芴、甲酚酚醛清漆型酚醛树脂、萘酚芳烷基型酚醛树脂、丙烯基酚醛树脂、丙烯基亚联苯基树脂、烯丙基酚醛树脂。这些具有酚性羟基的化合物(A)可以单独使用1种或组合2种以上而使用。
树脂组合物中的具有酚性羟基的化合物(A)的含量只要发挥本实施方式的效果就没有特别限定,相对于树脂组合物中的下述自由基聚合性化合物 (C)的总计量100质量份,优选5质量份以上且50质量份以下,从确保充分的助焊剂活性和溶剂溶解性的观点出发,更优选10质量份以上且45质量份以下,从确保充分的助焊剂活性、溶剂溶解性和树脂组合物的挠性的观点出发,进一步优选15质量份以上且40质量份以下。
〔I-2.金属离子捕捉剂(B)〕
作为金属离子捕捉剂(B),只要为能捕捉金属离子的化合物就没有特别限定。作为所捕捉的金属离子,没有特别限定,优选铜离子。
作为底部填充材料中的助焊剂成分,如果使用含羧基的化合物等较强的酸,则固化后使电极部、芯片或基板的铜布线腐蚀的作用也残留,因此,具有引起芯片的误操作或绝缘不良的问题。针对该问题,本发明人等推定:通过酸导致铜等金属腐蚀,离子化的金属借助固化物在连接端子间移动而析出、使端子间短路、即引起所谓迁移,从而产生绝缘性不良。因此,为了使用比含羧基的化合物的酸性还弱的具有酚性羟基的化合物作为助焊剂成分而进行金属氧化膜的去除,进行了深入研究。发现:如果单独使用酚类作为助焊剂成分,则对于酸解离常数大的苯酚,作用于金属氧化膜的质子浓度低,因此,自金属氧化膜溶解而生成的金属离子的浓度保持较小,无法进行充分的金属氧化膜去除。另一方面,在该反应部位添加金属离子捕捉剂,如果从反应部位去除金属离子,则由于保持体系的平衡的作用而加速金属离子的生成、即、氧化膜的分解,作为结果,氧化膜的去除量增加,金属氧化膜的去除成为可能。
作为金属离子捕捉剂(B),只要发挥本实施方式的效果就没有特别限定,从可以适合捕捉金属离子、特别是铜离子的方面出发,优选含有选自氮和氧中的至少1种元素作为配位原子。对于含有氮作为配位原子的金属离子捕捉剂,没有特别限定,例如可以举出胺类和胺衍生物。对于含有氧作为配位原子的金属捕捉剂,没有特别限定,例如可以举出醚衍生物和酮衍生物。
作为胺衍生物,例如可以举出咪唑衍生物、三唑衍生物、吡唑衍生物、三嗪衍生物、吡啶衍生物、三吡啶衍生物、联吡啶衍生物、菲咯啉衍生物、嘧啶衍生物、吡嗪衍生物、哒嗪衍生物、喹唑啉衍生物、卟啉衍生物、酞菁衍生物、和轮环藤宁(cyclen)衍生物。作为醚衍生物,例如可以举出冠醚衍生物。作为酮衍生物,例如可以举出二酮衍生物。
作为胺类,例如可以举出1,3-苯二胺、2,6-二氨基甲苯、1,3-二氨基芘、 2,4-二氨基甲苯、2,4,6-三甲基-1,3-苯二胺、2,4-二氨基二苯胺、3-乙酰氨基苯胺、1,2-二氨基-4-硝基苯、4-硝基-1,3-苯二胺、2-甲基-5-硝基苯胺、3,5-二氨基苯甲酸、2-氨基-1-甲基氨基-4-硝基苯、3-乙酰氨基-4-甲基苯胺、N-(叔丁氧基羰基)-1,3-苯二胺、3’-氨基-4’-甲氧基乙酰苯胺、3-(4-甲基-1-哌嗪基) 苯胺。
作为咪唑衍生物,例如可以举出咪唑、N-乙酰基咪唑、1-(α,4-二苯基苄基)咪唑、2,2’-(2,6-吡啶二基)双(苯并咪唑)、4-(4,5-二苯基-1H-咪唑-2-基)苯甲酸、2-(4-羟基苯基)-4,5-二苯基咪唑、5-氯-1-[1-[3-(2-氧代-1-苯并咪唑基)丙基]-4-哌啶基]苯并咪唑-2-酮、[5-(4-氟苯甲酰基)苯并咪唑-2-基]氨基甲酸甲酯、2-(4-氟苯基)-4,5-二苯基咪唑、2-十七烷基咪唑、 2-[[[3-甲基-4-(2,2,2-三氟乙氧基)-2-吡啶基]甲基]亚磺酰基]苯并咪唑、5- 甲氧基-2-[[(4-甲氧基-3,5-二甲基-2-吡啶基)甲基]硫代]苯并咪唑、[5-(苯基亚磺酰基)苯并咪唑-2-基]氨基甲酸甲酯、5-(二氟甲氧基)-2-[[(3,4-二甲氧基-2-吡啶基)甲基]硫代]苯并咪唑、4-(4-氟苯基)-2-(4-硝基苯基) -5-(4-吡啶基)-1H-咪唑、9-苯基-3,6-双[4-(1-苯基苯并咪唑-2-基)苯基] 咔唑、1-苯基-2-[3-(4,4,5,5-四甲基-1,3,2-二氧硼戊环-2-基)苯基]-1H-苯并咪唑、4’-[[4-甲基-6-(1-甲基-1H-苯并咪唑-2-基)-2-丙基-1H-苯并咪唑-1-基] 甲基]联苯-2-羧酸、4-甲酰基-1-三苯甲基咪唑、[5-(丙基硫代)苯并咪唑-2- 基]氨基甲酸甲酯、1-烯丙基咪唑、5-氨基-2-(4-氨基苯基)苯并咪唑、2-氨基苯并咪唑、5-氨基苯并咪唑、2-氨基-4,5-二氰基-1H-咪唑、4(5)-氨基-5 (4)-氰基咪唑、5-氨基-2-巯基苯并咪唑、1-(3-氨基丙基)咪唑、6-(1- 甲基-4-硝基咪唑-5-基)巯嘌呤、苯并咪唑、5-羧基苯并咪唑、2-(4-氨基苯基)苯并咪唑、1-苄基咪唑、1-苄基-2-甲基咪唑、2,2’-联咪唑、4,5-双(羟甲基)咪唑、4,5-双(羟甲基)-2-苯基咪唑、1,4-双[(1H-咪唑-1-基)甲基] 苯、N-叔丁氧基羰基咪唑、1-(二甲基氨磺酰基)-2-(叔丁基二甲基甲硅烷基)-1H-咪唑、1-(叔丁基二甲基甲硅烷基)咪唑、1-叔丁基咪唑、1-丁基咪唑、2-丁基咪唑、2-丁基-4-甲酰基咪唑、1,1’-羰基二咪唑、1-(2-氰基乙基)-2-甲基咪唑、1-(2-氰基乙基)-2-苯基咪唑、1-(2-氰基乙基)-2-十一烷基咪唑、4(5)-氰基甲基咪唑、1-(4-氰基苯基)咪唑、5-(3,3-二甲基三氮烯基)咪唑-4-羧基酰胺、5,6-二氨基-2-羟基苯并咪唑、2-丙基-1H-咪唑-4,5-二羧酸二乙酯、1-(2,6-二异丙基苯基)咪唑、1,2-二甲基苯并咪唑、5,6- 二甲基苯并咪唑、1-(二甲基乙基甲硅烷基)咪唑、1,2-二甲基咪唑、1H- 咪唑-4,5-二羧酸二甲酯、1-(二甲基异丙基甲硅烷基)咪唑、1,2-二甲基-5- 硝基咪唑、4,5-二苯基咪唑、4-(2-羟基-2-丙基)-2-丙基-1H-咪唑-5-羧酸乙酯、1-乙基咪唑、2-乙基咪唑、4(5)-乙基咪唑、2-咪唑羧酸乙酯、4-咪唑羧酸乙酯、2-乙基-4-甲基咪唑、1-甲基咪唑-2-羧酸乙酯、咪唑并[4,5-d]咪唑 -2,5(1H,3H)-四氢代二酮、2-羟基苯并咪唑、1-(10-羟基癸基)咪唑、2- (1-羟基乙基)苯并咪唑、2-(羟甲基)苯并咪唑、2-羟甲基-1-甲基咪唑、 4-羟甲基-5-甲基咪唑、2-羟甲基-1-甲基-5-硝基咪唑、2-(3-羟基丙基)苯并咪唑、1-咪唑乙酸、2-甲酰基咪唑、4-甲酰基咪唑、2-咪唑羧酸、4-咪唑羧酸、咪唑-4,5-二甲酰胺、1H-咪唑-4,5-二羧酸、1-(氰基甲基)咪唑、1-(4-甲酰基苯基)咪唑、1-异丙基咪唑、2-异丙基咪唑、[5-(苯甲酰基)苯并咪唑-2-基]氨基甲酸甲酯、1-甲基苯并咪唑、2-甲基苯并咪唑、5-甲基苯并咪唑、苯并咪唑-5-羧酸甲酯、5-(羟甲基)-1H-咪唑-4-羧酸甲酯、1-甲基咪唑、2-甲基咪唑、4-甲基咪唑、2-甲酰基-1-甲基咪唑、1H-咪唑-5-羧酸甲酯、1-甲基-4- 咪唑羧酸、4,5-二羧基-1-甲基-1H-咪唑、2-甲基-5-硝基咪唑-1-乙醇、4-甲基 -2-苯基咪唑、6-羧基-4-甲基-2-丙基苯并咪唑、2-甲基-1-乙烯基咪唑、5-硝基苯并咪唑、2-硝基咪唑、4-硝基咪唑、2-壬基苯并咪唑、1,1’-草酰基二咪唑、 1-(苯基乙基)咪唑、2-苯基苯并咪唑、1-苯基咪唑、2-苯基咪唑、4-苯基咪唑、2-(4-哌啶基)苯并咪唑、1-丙基咪唑、2-丙基咪唑、2-(2-吡啶基)苯并咪唑、2-(4-吡啶基)苯并咪唑、2,4,5-三苯基咪唑。
作为三唑衍生物,例如可以举出1-氨基苯并三唑、2-氨基苯并三唑、4- 氨基-3-肼基-5-巯基-1,2,4-三唑、3-氨基-5-巯基-1,2,4-三唑、3-氨基-5-甲基硫代-1H-1,2,4-三唑、N-(2-氨基苯基)-4-[1-[2-(3-噻吩基)乙基]-1H-1,2,3- 三唑-4-基]苯甲酰胺、3-氨基-1,2,4-三唑、4-氨基-1,2,4-三唑、1,2,3-苯并三唑、 1-甲酰基-1H-苯并三唑、5-羧基苯并三唑、1-(羟甲基)-1H-苯并三唑、2- (2H-苯并三唑-2-基)-4,6-双(1-甲基-1-苯基乙基)苯酚、9-(1H-苯并三唑 -1-基甲基)-9H-咔唑、1-叔丁氧基羰基-1,2,4-三唑、2-(5-叔丁基-2-羟基苯基)苯并三唑、1,1’-羰基二(1,2,4-三唑)、5-氯苯并三唑、2-(2-羟基-3-叔丁基-5-甲基苯基)-5-氯苯并三唑、1-(氯甲基)-1H-苯并三唑、3-(氯甲基) -1,2,4-三唑啉-5-酮、3-氯-1,2,4-三唑、3,5-二氨基-1,2,4-三唑、2-(3,5-二-叔戊基-2-羟基苯基)苯并三唑、4,7-二溴-2-(6-溴己基)苯并三唑、3,5-二溴-1,2,4- 三唑、2-(3,5-二-叔丁基-2-羟基苯基)-5-氯苯并三唑、3,5-二甲基-1,2,4-三唑、2,6-二(2H-1,2,3-三唑-4-基)吡啶、1-羟基-1H-1,2,3-三唑-4-羧酸乙酯、 1-[(9H-芴-9-基甲氧基)羰基氧基]苯并三唑、1-(甲酰胺甲基)-1H-苯并三唑、2-[2-羟基-5-[2-(甲基丙烯酰氧基)乙基]苯基]-2H-苯并三唑、2-(2-羟基-5-甲基苯基)苯并三唑、2-(2-羟基-5-叔辛基苯基)苯并三唑、1-羟基-6- (三氟甲基)苯并三唑、1-(异氰基甲基)-1H-苯并三唑、1-双(4-氰基苯基)甲基-1,2,4-三唑、3-巯基-4-甲基-4H-1,2,4-三唑、3-巯基-1,2,4-三唑、1- (甲氧基甲基)-1H-苯并三唑、1-甲基-1H-苯并三唑、5-甲基-1H-苯并三唑、 2,2’-亚甲基双[6-(苯并三唑-2-基)-4-叔辛基苯酚]、1,2,4-三唑-3-羧酸甲酯、 5-甲基-2-(2H-1,2,3-三唑-2-基)苯甲酸、1-(4-硝基苄基)-1,2,4-三唑、1,4- 二苯基-内苯胺基-二氢三唑、3-硝基-1,2,4-三唑、2-正辛基苯并三唑、1-(4-氯苯基)-4,4-二甲基-3-(1H-1,2,4-三唑-1-基甲基)-3-戊醇、1,2,4-三唑、 1H-1,2,3-三唑、1,2,4-三唑-3-甲酰胺、4-氮杂苯并三唑、1-羟基-7-氮杂苯并三唑、1-(4-氨基苯基)-1,2,4-三唑、1-(4-甲酰基苯基)-1,2,4-三唑、1-(2,4- 二氟苯甲酰基甲基)-1H-1,2,4-三唑、1-(4-氨基苄基)-1,2,4-三唑、3-(2- 吡啶基)-1,2,4-三唑、1-(三氟甲烷磺酰基)-1H-苯并三唑、3-(三氟甲基) -5-(2-吡啶基)-1,2,4-三唑、1-(2,4,6-三异丙基苯基磺酰基)-1,2,4-三唑、 1-(三甲基甲硅烷基)-1H-苯并三唑、1-[2-(三甲基甲硅烷基)乙氧基羰基氧基]苯并三唑、3-硝基-1-[2-(三甲基甲硅烷基)乙氧基羰基]-1H-1,2,4-三唑、三(1H-苯并三唑-1-基)甲烷、三(3-羟基丙基三唑基甲基)胺。
作为吡唑衍生物,例如可以举出吡唑、1-烯丙基-3,5-二甲基吡唑、3-氨基-5-叔丁基吡唑、5-氨基-1,3-二苯基吡唑、5-氨基-1-(2-羟基乙基)吡唑、 3-氨基-5-羟基吡唑、5-氨基-3-(4-甲氧基苯基)-1-苯基吡唑、3-氨基-5-(4- 甲氧基苯基)吡唑、5-氨基-3-甲基-1-苯基吡唑、4-氨基-1-甲基-3-丙基吡唑-5- 甲酰胺、3-氨基-1-甲基吡唑、3-氨基-5-甲基吡唑、5-氨基-3-甲基-1-对甲苯基吡唑、3-氨基-5-苯基吡唑、5-氨基-1-苯基吡唑、3-氨基吡唑、蒽并[1,9-cd] 吡唑-6(2H)-酮、1-苄基-1H-吡唑-4-羧基醛、N-(叔丁氧基羰基)-1H-吡唑-1-甲脒、N-(苄酯基)-1H-吡唑-1-甲脒、吡唑-3,5-二羧酸二乙酯、3,5-二异丙基吡唑、3,5-二甲基-1-羟甲基吡唑、3,5-二甲基-1-苯基吡唑、1,3-二甲基吡唑、1,5-二甲基吡唑、3,5-二甲基吡唑、1-氨基甲酰基-3,5-二甲基吡唑、1,3- 二甲基-1H-吡唑-5-羧酸、2,4-二氢-2,5-二甲基-3H-吡唑-3-酮、3,5-二苯基吡唑、 3,5-二(2-吡啶基)吡唑、5-氨基-1-甲基吡唑-4-羧酸乙酯、5-氨基-1-苯基吡唑-4-羧酸乙酯、3-氨基吡唑-4-羧酸乙酯、1,3-二甲基吡唑-5-羧酸乙酯、1,5- 二甲基吡唑-3-羧酸乙酯、3-甲基吡唑-5-羧酸乙酯、1-乙基-3-甲基吡唑-5-羧酸、1-乙基吡唑、吡唑-3-羧酸乙酯、4-吡唑羧酸乙酯、5-甲酰胺-1-[2-(甲酰氧基)乙基]吡唑、1,2-苯并吡唑、1-异丙基吡唑、1,5-二甲基吡唑-3-羧酸甲酯、5-甲基吡唑-3-羧酸甲酯、5-氨基甲酰基-1-甲基-4-硝基-3-丙基吡唑、3- 甲基-4-硝基吡唑、3-甲基-1-苯基吡唑、5-甲基-1-苯基吡唑-4-羧酸、1-甲基吡唑、3-甲基吡唑、4-甲基吡唑、4-甲酰基-1-甲基吡唑、5-甲酰基-1-甲基吡唑、 4-甲酰基-3-甲基吡唑、吡唑-3-羧酸甲酯、1-甲基吡唑-3-羧酸、1-甲基吡唑-4- 羧酸、1-甲基吡唑-5-羧酸、5-(羟甲基)-1-甲基吡唑、1-硝基吡唑、3-硝基吡唑、4-硝基吡唑、1-苯基吡唑、3-苯基吡唑、4-氨基吡唑、3-甲酰基吡唑、吡唑-3-羧酸、吡唑-4-羧酸、2,4-二氢-3H-吡唑-3-酮、5-(2-氨基苯基)吡唑、 4-(1H-吡唑-1-基)苯甲酸、3-(2-羟基苯基)吡唑、3-(2-吡啶基)吡唑、 1-(四氢-2H-吡喃-2-基)-1H-吡唑、1,3,5-三甲基吡唑。
作为三嗪衍生物,例如可以举出3-氨基-5,6-二甲基-1,2,4-三嗪、2-氨基-4- 甲氧基-6-甲基-1,3,5-三嗪、6-氨基-1,3,5-三嗪-2,4-二醇、2,4-二氨基-6-羟基 -1,3,5-三嗪、2-氨基-4-羟基-1,3,5-三嗪、2,4-二氨基-6-苯基-1,3,5-三嗪、2-(叔丁基氨基)-4-(环丙基氨基)-6-(甲基硫代)-1,3,5-三嗪、2,4-二氨基-6-(环丙基氨基)-1,3,5-三嗪、2,4-二氨基-6-丁基氨基-1,3,5-三嗪、2,4-二氨基-6-二烯丙基氨基-1,3,5-三嗪、2,4-二氨基-6-二乙基氨基-1,3,5-三嗪、2,4-二氨基-6- 二甲基氨基-1,3,5-三嗪、2,4-二氨基-6-异丙氧基-1,3,5-三嗪、2,4-二氨基-6-甲氧基-1,3,5-三嗪、2,4-二氨基-6-[2-(2-甲基-1-咪唑基)乙基]-1,3,5-三嗪、2,4- 二氨基-6-甲基-1,3,5-三嗪、2,4-二氨基-1,3,5-三嗪、3-(二乙氧基磷酰氧基) -1,2,3-苯并三嗪-4(3H)-酮、3,4-二氢-3-羟基-4-氧代-1,2,3-苯并三嗪、3,4- 二氢-4-氧代-1,2,3-苯并三嗪、2,4-二甲氧基-1,3,5-三嗪、2,4,6-三氨基-1,3,5- 三嗪、4-氨基-3-甲基-6-苯基-1,2,4-三嗪-5-酮、2-甲氧基-4-甲基-6-(甲基氨基) -1,3,5-三嗪、1,3,5-三(甲基)丙烯酰基六氢-1,3,5-三嗪、1,3,5-三嗪、1,3,5- 三甲基六氢-1,3,5-三嗪、2-乙烯基-4,6-二氨基-1,3,5-三嗪。
作为吡啶衍生物,例如可以举出5-溴吡啶-3-甲酰胺、4-(4-氨基苯氧基) -N-甲基-2-吡啶甲酰胺、2,6-双[(2R,4S,5S)-1-苄基-4,5-二苯基咪唑烷-2-基] 吡啶、2,6-双[3-(9H-咔唑-9-基)苯基]吡啶、2,6-双[(2S,5S)-4,4-二苯基-1- 氮杂-3-氧杂双环[3.3.0]辛烷-2-基]吡啶、2,6-双[(2S,4S)-4-甲基-5,5-二苯基噁唑烷-2-基]吡啶、2,6-双(9H-咔唑-9-基)吡啶、3,5-二(1-芘基)吡啶、2,6- 双(2-苯并咪唑基)吡啶、(R,R)-2,6-双(4-异丙基-2-噁唑啉-2-基)吡啶、 (S,S)-2,6-双(4-异丙基-2-噁唑啉-2-基)吡啶、(R,R)-2,6-双(4-苯基-2- 噁唑啉-2-基)吡啶、(S,S)-2,6-双(4-苯基-2-噁唑啉-2-基)吡啶、2,2’-二硫代双(5-硝基吡啶)、6,6’-二硫代双(3-吡啶羧酸)、2-[N,N-双(三氟甲基磺酰基)氨基]吡啶、2-(三溴甲烷磺酰基)吡啶、N-(异丙基氨基甲酰基)-4- (间甲苯基氨基)吡啶-3-磺酰胺、4-甲氧基-2-(三丁基甲锡烷基)吡啶、2- (三丁基甲锡烷基)吡啶、2,4,6-三苯基吡啶、2-乙酰氨基-5-碘吡啶、2-氨基 -5-溴-3-碘吡啶、2-氨基-5-氯-3-碘吡啶、2-氨基-3,5-二溴-6-甲基吡啶、2-氨基 -3,5-二溴吡啶、3-氨基-2,5-二溴吡啶、3-氨基-2,6-二溴吡啶、4-氨基-3,5-二溴吡啶、4-(4-氨基-3-氟苯氧基)-N-甲基-2-吡啶甲酰胺、3-氨基-2-甲氧基-5- (4,4,5,5-四甲基-1,3,2-二氧硼戊环-2-基)吡啶、2-氨基-7-异丙基-5-氧代色烯并[2,3-b]吡啶-3-羧酸、3-苄氧基-5-溴吡啶、2,6-双(溴甲基)吡啶、2-溴-6- 苄氧基吡啶、2-溴-3-氯-5-(三氟甲基)吡啶、2-溴-5-碘-3-甲基吡啶、2-溴-3- (4,4,5,5-四甲基-1,3,2-二氧硼戊环-2-基)吡啶、2-溴-6-(4,4,5,5-四甲基-1,3,2- 二氧硼戊环-2-基)吡啶、4-[(叔丁氧基羰基氨基)甲基]吡啶-2-羧酸、2-氯 -N-(2-氯-4-甲基吡啶-3-基)吡啶-3-甲酰胺、3,5-二溴-4-甲酰基吡啶、4,7- 二溴[1,2,5]噻二唑并[3,4-c]吡啶、4-(4-二乙基氨基苯基偶氮)吡啶、2-(2,4- 二硝基苄基)吡啶、4-(2,4-二硝基苄基)吡啶、3-氯-5-(三氟甲基)吡啶-2- 羧酸乙酯、5-乙基-2-[2-(4-硝基苯氧基)乙基]吡啶、5-溴-2-氯-3-吡啶羧酸甲酯、2,2’-[亚甲基双(二甲基亚甲硅基)]双吡啶、2-(N-L-苯基氨基丙醇) -5-硝基吡啶、2-苯基-5-(4,4,5,5-四甲基-1,3,2-二氧硼戊环-2-基)吡啶、3-[3- (4,4,5,5-四甲基-1,3,2-二氧硼戊环-2-基)苯基]吡啶、4-[3-(4,4,5,5-四甲基 -1,3,2-二氧硼戊环-2-基)苯基]吡啶、4-[4-(4,4,5,5-四甲基-1,3,2-二氧硼戊环 -2-基)苯基]吡啶、4-(间甲苯基氨基)-3-氨磺酰基吡啶、5-(间甲苯基)-5H- 吡咯并[3,2-c:4,5-c’]二吡啶、3-(3,4-二甲氧基苯基)-2-(吡啶-3-基)(甲基)丙烯腈、3-(3,5-二氯苯基)-2-(吡啶-3-基)(甲基)丙烯腈、2-乙酰氨基-5-溴-4-甲基吡啶、2-乙酰氨基-5-溴吡啶、2-乙酰基-6-溴吡啶、3-乙酰基-5-溴吡啶、5-乙酰基-2-溴吡啶、2-氨基-3-苄氧基吡啶、2-氨基-3-溴-5-氯吡啶、 3-氨基-2-溴-5-氯吡啶、3-氨基-5-溴-2-氯吡啶、3-氨基-6-溴-2-氯吡啶、5-氨基-3-溴-2-氯吡啶、2-氨基-3-溴-5,6-二甲基吡啶、2-氨基-5-溴-4-甲基-3-硝基吡啶、2-氨基-5-溴-3-硝基吡啶、2-氨基-6-(叔丁氧基羰基氨基)吡啶、2- 氨基-5-碘-3-甲基吡啶、2-氨基-5-碘-4-甲基吡啶、2-氨基-3-碘吡啶。
作为三吡啶衍生物,例如可以举出4’-(4-溴苯基)-2,2’:6’,2”-三吡啶、 4’-溴-2,2’:6’,2”-三吡啶、2,2’:6’,2”-三吡啶-4’-膦酸二乙酯、1,4-二[[2,2’: 6’,2”-三吡啶]-4’-基]苯、4’-(甲氧基羰基)-2,2’:6’,2”-三吡啶、2,2’:6’,2”- 三吡啶、2,2’:6’,2”-三吡啶-4,4’,4”-三羧酸三甲酯。
作为联吡啶衍生物,例如可以举出2,2’-联吡啶-6-甲腈、2,2’-联吡啶-3,3’- 二羧酸、2,2’-联吡啶-4,4’-二羧酸、2,2’-联吡啶-5,5’-二羧酸、2,2’-联吡啶-6,6’- 二羧酸、2,2’-联吡啶-3,3’-二醇、2,2’-联吡啶-6,6’-二醇、2,2’-联吡啶、2,4’- 联吡啶、3,3’-联吡啶、4,4’-联吡啶、6,6’-双(氯甲基)-2,2’-联吡啶、4,4’-双 (5-己基-2-噻吩基)-2,2’-联吡啶、4,4’-双(羟甲基)-2,2’-联吡啶、1,2-双(4’- 甲基-2,2-联吡啶-4-基)乙烷、5,5’-双(三氟甲基)-2,2’-联吡啶、6-溴-2,2’- 联吡啶、6-溴-4,4’-二甲基-2,2’-联吡啶、4-(溴甲基)-4’-甲基-2,2’-联吡啶、 4-(氯甲基)-4’-甲基-2,2’-联吡啶、4,4’-二氨基-2,2’-联吡啶、2,2’-联吡啶-6,6’- 二胺、4,4’-二溴-2,2’-联吡啶、5,5’-二溴-2,2’-联吡啶、6,6’-二溴-2,2’-联吡啶、 4,4’-二-叔丁基-2,2’-联吡啶、2,2’-联吡啶-6,6’-二甲腈、4,4’-二甲氧基羰基 -2,2’-联吡啶、6,6’-二甲氧基羰基-2,2’-联吡啶、4,4’-二甲基-(2,2’-联吡啶) -3-醇、4-羟甲基-4’-甲基-2,2’-联吡啶、6’-甲氧基-2,3’-联吡啶。
作为菲咯啉衍生物,例如可以举出2,9-二甲基-4,7-二苯基-1,10-菲咯啉、 4,7-二苯基-1,10-菲咯啉、2-溴-1,10-菲咯啉、3-溴-1,10-菲咯啉、5-溴-1,10-菲咯啉、2-氯-1,10-菲咯啉、5-氯-1,10-菲咯啉、3,8-二溴-1,10-菲咯啉、2,9-二丁基-1,10-菲咯啉、2,9-二丁基-5-苦氨基-1,10-菲咯啉、2,9-二氯-1,10-菲咯啉、 4,7-二羟基-1,10-菲咯啉、4,7-二甲基-1,10-菲咯啉、5,6-二甲基-1,10-菲咯啉、 2,9-二甲基-5-苦氨基-1,10-菲咯啉、2,9-二苯基-1,10-菲咯啉、2-甲基-1,10-菲咯啉、5-硝基-1,10-菲咯啉、1,10-菲咯啉-5,6-二酮、(1S)-3-(1,10-菲咯啉-2- 基)-2’-苯基-[1,1’-联萘]-2-醇、3,5,6,8-四溴-1,10-菲咯啉、3,4,7,8-四甲基-1,10- 菲咯啉。
作为嘧啶衍生物,例如可以举出嘧啶、4-甲基嘧啶、5-氨基嘧啶、2-氨基嘧啶、4-氨基嘧啶、4(3H)-嘧啶酮、2-氯嘧啶、2-巯基嘧啶、2-氰基嘧啶、4,6-二氯嘧啶、4,6-二甲基嘧啶、2,5-二氯嘧啶、2,4-二氯嘧啶、2-氯-4- 甲基嘧啶、4-甲氧基嘧啶、2-氯-5-氟嘧啶、2-氯-5-甲基嘧啶、4-氯-2-甲基嘧啶、4,6-二羟基嘧啶、2-氯-4,6-二甲基嘧啶、4,6-二甲氧基嘧啶、嘧啶-5-羧酸、 5-氨基-4-氯嘧啶、2-氯-5-乙基嘧啶、2-氯-5-甲氧基嘧啶、4,6-二氨基嘧啶、 5-嘧啶基硼酸、嘧啶-2-羧酸、2-氨基-4-甲基嘧啶、2-氨基-5-氯嘧啶、4,6-二甲基-2-巯基嘧啶、嘧啶-2-羧酸甲酯、2,4-二甲氧基嘧啶、2-氨基-4,6-二甲基嘧啶、2,4-二氨基嘧啶、4,6-二甲基-2-羟基嘧啶、4-氨基-2-氯嘧啶、4-氯-6- 羟基嘧啶、2-甲基硫代-4-嘧啶醇、4-氯-6-甲氧基嘧啶、4,5-二氨基嘧啶、4,6- 二羟基-2-甲基嘧啶、嘧啶-4-羧酸、2,4,6-三氨基嘧啶、2-氨基-5-硝基嘧啶、 4-氨基-6-氯嘧啶、4-氨基嘧啶-5-甲腈、4,6-二羟基-2-巯基嘧啶、2-氨基-4-氯 -6-甲基嘧啶、2-氨基-4,6-二羟基嘧啶、4,6-二氨基-2-巯基嘧啶、2,4-二甲基-6- 羟基嘧啶、2,4-二羟基-5-甲氧基嘧啶、4-氨基-2,6-二甲基嘧啶、4-氨基-6-羟基嘧啶、2-氨基嘧啶-5-硼酸、6-氯-2,4-二氨基嘧啶、2-氨基-4-羟基-6-甲基嘧啶、4-氨基-2-氯-5-氟嘧啶、6-氯嘧啶-4,5-二胺、2-氨基-4-氯-6-羟基嘧啶、2- 氨基-4-甲氧基-6-甲基嘧啶、6-羟基-4-嘧啶羧酸、4-氨基-5-氟-2-甲氧基嘧啶、 2,4-二氨基-6-羟基嘧啶、4,5-二氨基-6-羟基嘧啶、2,4-二氨基-6-甲氧基嘧啶、 4-氨基-2-甲基-5-嘧啶甲醇、7H-吡咯并[2,3-d]嘧啶、8-氮杂腺嘌呤、6-氨基嘌呤、4-羟基吡唑并[3,4-d]嘧啶、4-氨基吡唑并[3,4-d]嘧啶、2-氨基嘌呤、8-氮杂黄嘌呤、4-氨基-2-氧代-1,2-二氢嘧啶、5-羟基尿嘧啶、2-氨基-4(1H)- 嘧啶酮、4-氨基-5-氟-2-羟基嘧啶、3,7-二氢-4H-吡咯并[2,3-d]嘧啶-4-酮、2- 氯-5-氟-4-嘧啶酮、5-氟-2-甲氧基-4-嘧啶酮、次黄嘌呤、5-溴嘧啶、2-溴嘧啶、5-溴-2-氟嘧啶、5-溴-2-氯嘧啶、5-溴-2-甲基嘧啶、2,4,6-三氯嘧啶、嘧啶-2- 磺酰基氟化物、4,5,6-三氯嘧啶、2,2’-联嘧啶、4-氯-2-(甲基硫代)嘧啶、4,6- 二氯-2-甲基嘧啶、5-溴-2-羟基嘧啶、4,6-二氯-5-甲基嘧啶、5-氨基-4,6-二氯嘧啶、2-氨基-5-溴嘧啶、5-溴-2-甲氧基嘧啶、5-氯-2,4,6-三氟嘧啶、4,6-二氯 -2-(甲基硫代)嘧啶、2-氨基-4,6-二氯嘧啶、2-氨基-4,6-二氯嘧啶、2,4,5- 三氯嘧啶、2,4-二氯-5-氟嘧啶、2-氯-4-(三氟甲基)嘧啶、4,6-二氯-5-甲氧基嘧啶、2-氯-5-硝基嘧啶、2,4-二氯-5-甲基嘧啶、2,4-二氯-6-甲基嘧啶、2,4,6- 三甲氧基嘧啶、2,4-二氯-5-甲氧基嘧啶、2-氯-4,6-二甲氧基嘧啶、4,6-二甲基 -2-(甲基磺酰基)嘧啶、5-氨基-4,6-二氯-2-甲基嘧啶、4,6-二羟基-2-甲基硫代嘧啶、2,5-二氨基-4,6-二氯嘧啶、2-氨基-4,6-二甲氧基嘧啶、2-氨基-4-(三氟甲基)嘧啶、4-氯-6-甲基-2-(甲基硫代)嘧啶、2-羟基-4-(三氟甲基)嘧啶、2-甲氧基-5-嘧啶基硼酸、4-羟基-6-三氟甲基嘧啶、嘧啶-4-羧酸乙酯、2- 苯基嘧啶、4,6-二羟基-5-硝基嘧啶、2,4-二氯-5-硝基嘧啶、4-氨基-2,6-二氯嘧啶、6-氯-2,4-二甲氧基嘧啶、4-氨基-5,6-二氯嘧啶、2,4,6-三氨基-5-亚硝基嘧啶、2-氨基-4-氯-6-甲氧基嘧啶、4-羟基-2-甲基-6-(三氟甲基)嘧啶、4- 氨基-6-氯-2-(甲基硫代)嘧啶、2-肼基-4-(三氟甲基)嘧啶、6-氨基-2,4- 二甲氧基嘧啶、4-羟基-2-巯基-6-(三氟甲基)嘧啶、4-氨基-5-氯-2,6-二甲基嘧啶、2-(1-哌嗪基)嘧啶、4-氨基-2,6-二羟基-5-亚硝基嘧啶、4-氨基-2-二甲基氨基-6-羟基-5-亚硝基嘧啶、1-(2-嘧啶基)-1H-吲哚、4-氯-7H-吡咯并 [2,3-d]嘧啶、2,4-二氯-7H-吡咯并[2,3-d]嘧啶、4,6-二溴嘧啶、2,5-二溴嘧啶、 2-氯-5-碘嘧啶、5-溴-2-叔丁基嘧啶、5-溴-2,4-二氯嘧啶、2,4,5,6-四氯嘧啶、 5-溴-4-氯-2-(甲基硫代)嘧啶、4,6-二氯-2-(甲基磺酰基)嘧啶、5-溴嘧啶 -2-羧酸甲酯、5-溴-2,4-二甲氧基嘧啶、2,4,6-三氯-5-甲酰基嘧啶、2-(叔丁氧基羰基硫代)-4,6-二甲基嘧啶、4,6-二甲氧基-2-(甲基磺酰基)嘧啶、2-氨基-4,6-二氯-5-甲酰胺嘧啶、5-氨基-4,6-二氯-2-(丙基硫代)嘧啶、4,6-二氯 -2-苯基嘧啶、2,4-二氯嘧啶-5-羧酸乙酯、5-溴-2-(甲基硫代)嘧啶-4-羧酸、 4-氯-2-(甲基硫代)嘧啶-5-羧酸乙酯、5-氯-2-(甲基硫代)嘧啶-4-羧酸、 2-氯-5-(4,4,5,5-四甲基-1,3,2-二氧硼戊环-2-基)嘧啶、2-氨基-4,6-二苯基嘧啶、2-氨基-5-(4,4,5,5-四甲基-1,3,2-二氧硼戊环-2-基)嘧啶、2-(4-吗啉代) -4,6-二氯嘧啶、5-(4-氯苯基)-6-乙基-2,4-嘧啶二胺、2,4-二氯-6-(4-吗啉代)嘧啶、4-氯-N-(4,5-二氢-1H-咪唑-2-基)-6-甲氧基-2-甲基-5-嘧啶胺、2,4-二氯噻吩并[3,2-d]嘧啶、4-氯苯并呋喃并[3,2-d]嘧啶。
作为吡嗪衍生物,例如可以举出吡嗪、2-乙酰基-3-乙基吡嗪、2-乙酰基 -3-甲基吡嗪、2-乙酰基吡嗪、2-氨基-5-溴-3-甲氧基吡嗪、2-氨基-5-溴吡嗪、 2-氨基-3-氯吡嗪、2-氨基-5-氯吡嗪、2-氨基-6-氯吡嗪、2-氨基-3,5-二溴吡嗪、 2-(氨基甲基)-5-甲基吡嗪、2-氨基-6-甲基吡嗪、2-氨基-5-苯基吡嗪、2-氨基吡嗪、3-氨基吡嗪-2-羧酸、2,2’-联吡嗪、2-溴-5-羟基吡嗪、2-溴吡嗪、2- 仲丁基-3-甲氧基吡嗪、2-丁基-3-甲基吡嗪、2-叔丁基吡嗪、2-氯-3,5-二甲基吡嗪、3-氯-2,5-二甲基吡嗪、5-氯-2,3-二苯基吡嗪、2-氯-6-甲基吡嗪、氯吡嗪、3-氯吡嗪-2-甲酰胺、5-氯吡嗪-2-羧酸、6-氯吡嗪-2-羧酸、6,8-二溴咪唑并[1,2-a]吡嗪、2,5-二溴吡嗪、2,6-二溴吡嗪、2,3-二氯吡嗪、2,6-二氯吡嗪、氰基吡嗪、5,6-二氨基-2,3-二氰基吡嗪、5,6-二氯-2,3-二氰基吡嗪、2,3-二氰基-5-甲基吡嗪、2,3-二氰基吡嗪、2,3-二乙基-5-甲基吡嗪、2,3-二乙基吡嗪、 2,3-二甲基吡嗪、2,5-二甲基吡嗪、2,6-二甲基吡嗪、2-乙氧基-3-乙基吡嗪、 2-乙氧基-3-异丙基吡嗪、2-乙氧基-3-甲基吡嗪、2-乙氧基吡嗪、5-乙基-2,3- 二甲基吡嗪、2-乙基-3-甲基吡嗪、2-乙基-3-(甲基硫代)吡嗪、3-氧代-3- (吡嗪-2-基)丙酸乙酯、2-乙基吡嗪、2-糠基硫代-3-甲基吡嗪、N-[4-(3- 环己基脲基磺酰基)苯乙基]-5-甲基-2-吡嗪甲酰胺、2-羟基-3-甲基吡嗪、3- 羟基吡嗪-2-甲酰胺、2-碘吡嗪、2-异丁基-3-甲氧基吡嗪、2-异丁基-3-甲基吡嗪、2-异丙基-3-甲氧基吡嗪、(2-巯基乙基)吡嗪、2-甲氧基-3-甲基吡嗪、 2-甲氧基吡嗪、3-氨基-6-溴吡嗪-2-羧酸甲酯、3-氨基吡嗪-2-羧酸甲酯、3-氯吡嗪-2-羧酸甲酯、3,5-二氨基-6-氯吡嗪-2-羧酸甲酯、5H-5-甲基-6,7-二氢环戊并吡嗪、2-甲基-3-异丙氧基吡嗪、2-甲基-3-(甲基硫代)吡嗪、2-甲基-3- 丙基吡嗪、2-甲基吡嗪、2-吡嗪羧酸甲酯、5-甲基吡嗪-2-羧酸、2-羧基-5-甲基吡嗪4-氧化物、2-(甲基硫代)吡嗪、苯并[d]吡嗪-1(2H)酮、2-丙基吡嗪、吡嗪酰胺、吡嗪羧酸、2,3-吡嗪二羧酸、吡嗪-2,3-二羧酸单酰胺、2-吡嗪甲醇、4-氨基-N-(3-甲氧基吡嗪-2-基)苯磺酰胺、1,4,5,6-四氢-5,6-二氧杂 -2,3-吡嗪二甲腈、2,3,5,6-四甲基吡嗪、2,3,5-三甲基吡嗪、2-乙烯基吡嗪。
作为哒嗪衍生物,例如可以举出哒嗪、3-氨基-6-氯哒嗪、3-氨基哒嗪、 3-溴咪唑并[1,2-b]哒嗪、6-氯咪唑并[1,2-b]哒嗪、3-氯-6-甲氧基哒嗪、3-氯-6- 甲基哒嗪、3-氯-6-苯基哒嗪、6-氯-3(2H)-哒嗪酮、3,6-二溴哒嗪、3,6-二氯-4-甲基哒嗪、3,5-二氯哒嗪、3,6-二氯哒嗪、4,5-二氯-3(2H)-哒嗪酮、 6-羟基哒嗪-3-羧酸、咪唑并[1,2-b]哒嗪、马来酰肼、3-甲氧基哒嗪、甲基马来酰肼、3-甲基哒嗪、4-甲基哒嗪、3-羟基-6-甲基哒嗪、3-羟基-6-苯基哒嗪、哒嗪-4-羧酸、4-氨基-N-(6-甲氧基-3-吡嗪基)苯磺酰胺、1,4,5,6-四氢-6-氧代哒嗪-3-羧酸、3,4,6-三氯哒嗪。
作为喹唑啉衍生物,例如可以举出喹唑啉、6-乙酰氧基-7-甲氧基-3H-喹唑啉-4-酮、4-氨基-2-氯-6,7-二甲氧基喹唑啉、7-苄氧基-6-甲氧基-3H-喹唑啉 -4-酮、6,7-双(2-甲氧基乙氧基)-3H-喹唑啉-4-酮、6-溴-4-羟基喹唑啉、N-4- (3-溴苯基)喹唑啉-4,6-二胺、4-氯-6,7-二甲氧基喹唑啉、4-[3-氯-4-(3-氟苄氧基)苯基氨基]-6-碘喹唑啉、4-氯-6-碘喹唑啉、2-(氯甲基)-4-甲基喹唑啉、7-氯-6-硝基-4-羟基喹唑啉、2-氯-4-苯基喹唑啉、(E)-N-[4-[(3-氯-4- 氟苯基)氨基]-7-甲氧基喹唑啉-6-基]-4-(哌啶-1-基)丁-2-烯酰胺、N,N’-二苄基喹唑啉-2,4-二胺、2,4-二氯-6,7-二甲氧基喹唑啉、6,7-二甲氧基喹唑啉-2,4-二酮、6,7-二甲氧基-3H-喹唑啉-4-酮、7-氟-4-羟基喹唑啉、7-氟-6-硝基喹唑啉-4(1H)-酮、4-羟基喹唑啉、6-碘-4-羟基喹唑啉、3-[2-[4-(4-氟苯甲酰基)-1-哌啶基]乙基]-2,4(1H,3H)-喹唑啉二酮、8,13-二氢吲哚并[2’,3’: 3,4]吡啶并[2,1-b]喹唑啉-5(7H)-酮、N-(3-氯苯基)-6,7-二甲氧基-4-喹唑啉胺。
作为卟啉衍生物,例如可以举出卟啉、5,15-二苯基卟啉、 2,3,7,8,12,13,17,18-八乙基卟啉、2,3,7,8,12,13,17,18-八氟-5,10,15,20-四(五氟苯基)卟啉、meso-四苯基卟啉、四苯基卟啉、5,10,15,20-四(4-甲氧基苯基)卟啉、5,10,15,20-四(2,6-二氯苯基)卟啉、5,10,15,20-四(4-羧基甲基氧基苯基)卟啉、5,10,15,20-四(4-羟基苯基)卟啉、5,10,15,20-四(2,4,6- 三甲基苯基)卟啉、5,10,15,20-四(五氟苯基)卟啉、5,10,15,20-四(3,5-二羟基苯基)卟啉、5,10,15,20-四(3,5-二甲氧基苯基)卟啉、5,10,15,20-四(4- 吡啶基)卟啉、5,10,15,20-四(对甲苯基)卟啉。
作为酞菁衍生物,例如可以举出酞菁、萘酞菁、Azulenocyanine。
作为轮环藤宁衍生物,例如可以举出1,4,7,10-四氮杂环十二烷、1,4,7,10- 四氮杂环十二烷-1,4,7,10-四乙酸、1,4,7,10-四氮杂环十二烷-1,4,7-三乙酸三- 叔丁酯、1,4,7,10-四氮杂环十二烷-1,4,7,10-四乙酸三-叔丁酯、1,4,7,10-四苄基-1,4,7,10-四氮杂环十二烷。
作为冠醚衍生物,例如可以举出12-冠4-醚、2-(羟甲基)-12-冠4-醚、苯并-12-冠4-醚、15-冠5-醚、2-(羟甲基)-15-冠5-醚、苯并-15-冠5-醚、二苯并-15-冠5-醚、4’-溴苯并-15-冠5-醚、4’-氨基苯并-15-冠5-醚、4’-甲酰基苯并-15-冠5-醚、4’-乙酰基苯并-15-冠5-醚、4’-羧基苯并-15-冠5-醚、4’-硝基苯并-15-冠5-醚、18-冠6-醚、2-(羟甲基)-18-冠6-醚、二环己-18-冠6-醚、苯并-18-冠6-醚、二苯并-18-冠6-醚、4’-溴苯并-18-冠6-醚、4’-氨基苯并-18-冠 6-醚、4’-甲酰基苯并-18-冠6-醚、4’-乙酰基苯并-18-冠6-醚、4’-羧基苯并-18- 冠6-醚、4’-硝基苯并-18-冠6-醚、21-冠-7-醚、二苯并-21-冠-7-醚、24-冠-8- 醚、二苯并-24-冠-8-醚。
作为二酮衍生物,例如从与金属离子形成复合体的观点出发,可以举出 1,3-二苯基-1,3-丙二酮、1-(2-均三甲苯)-1,3-丁二酮、1,3-双(4-甲氧基苯基)-1,3-丙二酮、1-(4-叔丁基苯基)-3-(4-甲氧基苯基)-1,3-丙二酮、和 (E,E)-1,7-双(4-羟基-3-甲氧基苯基)-1,6-庚二烯-3,5-二酮的1,3-二酮。
作为金属离子捕捉剂(B),从确保树脂组合物的清漆的良好的保存稳定性的观点出发,例如优选三嗪衍生物、联吡啶衍生物、和二酮衍生物,更优选2,4-二氨基-6-甲基-1,3,5-三嗪、2,2’-联吡啶、1,3-二苯基-1,3-丙二酮、1-(2- 均三甲苯)-1,3-丁二酮、1,3-双(4-甲氧基苯基)-1,3-丙二酮、1-(4-叔丁基苯基)-3-(4-甲氧基苯基)-1,3-丙二酮、和(E,E)-1,7-双(4-羟基-3-甲氧基苯基)-1,6-庚二烯-3,5-二酮,从确保溶剂溶解性和分子的运动性的观点出发,进一步优选1-(4-叔丁基苯基)-3-(4-甲氧基苯基)-1,3-丙二酮和(E,E)-1,7-双(4-羟基-3-甲氧基苯基)-1,6-庚二烯-3,5-二酮。
这些金属离子捕捉剂(B)可以单独使用1种或组合2种以上而使用。
树脂组合物中的金属离子捕捉剂(B)的含量只要发挥本实施方式的效果就没有特别限定,相对于树脂组合物中的下述自由基聚合性化合物(C) 的总计量100质量份,优选5质量份以上且50质量份以下,从确保溶剂溶解性和充分的助焊剂活性的观点出发,更优选10质量份以上且45质量份以下,从确保充分的助焊剂活性和树脂组合物的挠性的观点出发,进一步优选15质量份以上且40质量份以下。
〔I-3.自由基聚合性化合物(C)〕
作为自由基聚合性化合物(C),只要为具有通过自由基而聚合的官能团的物质就没有特别限定,例如可以举出(甲基)丙烯酸酯化合物、马来酰亚胺化合物和丙烯基化合物。
作为(甲基)丙烯酸酯化合物,例如可以举出(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸异丙酯、(甲基)丙烯酸异丁酯、乙二醇二(甲基)丙烯酸酯、二乙二醇二(甲基)丙烯酸酯、三羟甲基丙烷三(甲基) 丙烯酸酯、四羟甲基甲烷四(甲基)丙烯酸酯、2-羟基-1,3-二(甲基)丙烯酰氧基丙烷、2,2-双[4-((甲基)丙烯酰氧基甲氧基)苯基]丙烷、2,2-双[4- ((甲基)丙烯酰氧基聚乙氧基)苯基]丙烷、(甲基)丙烯酸二环戊烯酯、(甲基)丙烯酸三环癸酯、三((甲基)丙烯酰氧基乙基)异氰脲酸酯、和氨基甲酸酯(甲基)丙烯酸酯。根据需要可以适宜使用例如氢醌、甲醚氢醌类的阻聚剂。
作为马来酰亚胺化合物,只要为分子中具有1个以上马来酰亚胺基的化合物就没有特别限定。例如可以举出N-苯基马来酰亚胺、N-羟基苯基马来酰亚胺、双(4-马来酰亚胺基苯基)甲烷、4,4-二苯基甲烷双马来酰亚胺、双 (3,5-二甲基-4-马来酰亚胺基苯基)甲烷、双(3-乙基-5-甲基-4-马来酰亚胺基苯基)甲烷、双(3,5-二乙基-4-马来酰亚胺基苯基)甲烷、苯基甲烷马来酰亚胺、邻亚苯基双马来酰亚胺、间亚苯基双马来酰亚胺、对亚苯基双马来酰亚胺、邻亚苯基双柠康酰亚胺、间亚苯基双柠康酰亚胺、对亚苯基双柠康酰亚胺、2,2-双(4-(4-马来酰亚胺基苯氧基)-苯基)丙烷、3,3-二甲基-5,5- 二乙基-4,4-二苯基甲烷双马来酰亚胺、4-甲基-1,3-亚苯基双马来酰亚胺、1,6- 双马来酰亚胺-(2,2,4-三甲基)己烷、4,4-二苯醚双马来酰亚胺、4,4-二苯基砜双马来酰亚胺、1,3-双(3-马来酰亚胺基苯氧基)苯、1,3-双(4-马来酰亚胺基苯氧基)苯、4,4-二苯基甲烷双柠康酰亚胺、2,2-双[4-(4-柠康酰亚胺基苯氧基)苯基]丙烷、双(3,5-二甲基-4-柠康酰亚胺基苯基)甲烷、双(3-乙基-5-甲基-4-柠康酰亚胺基苯基)甲烷、双(3,5-二乙基-4-柠康酰亚胺基苯基) 甲烷、聚苯基甲烷马来酰亚胺、酚醛清漆型马来酰亚胺化合物、联苯芳烷基型马来酰亚胺化合物、2,2-双{4-(4-马来酰亚胺基苯氧基)苯基}丙烷、1,2- 双(马来酰亚胺基)乙烷、1,4-双(马来酰亚胺基)丁烷、1,6-双(马来酰亚胺基)己烷、N,N’-1,3-亚苯基二马来酰亚胺、N,N’-1,4-亚苯基二马来酰亚胺、 N-苯基马来酰亚胺、下述式(1)所示的马来酰亚胺化合物、下述式(2)所示的马来酰亚胺化合物、和下述式(3)所示的马来酰亚胺化合物。
其中,从对有机溶剂的溶解性的观点出发,优选2,2-双{4-(4-马来酰亚胺苯氧基)苯基}丙烷、1,2-双(马来酰亚胺)乙烷、1,4-双(马来酰亚胺) 丁烷、1,6-双(马来酰亚胺)己烷、N,N’-1,3-苯二马来酰亚胺、N,N’-1,4-苯二马来酰亚胺、N-苯基马来酰亚胺、下述式(1)所示的马来酰亚胺化合物、下述式(2)所示的马来酰亚胺化合物、和下述式(3)所示的马来酰亚胺化合物,更优选2,2-双{4-(4-马来酰亚胺苯氧基)苯基}丙烷、下述式(1) 所示的马来酰亚胺化合物、下述式(2)所示的马来酰亚胺化合物、和下述式(3)所示的马来酰亚胺化合物。作为下述式(3)所示的马来酰亚胺化合物,优选双-(3-乙基-5-甲基-4-马来酰亚胺苯基)甲烷。
式(1)中,R1各自独立地表示氢原子或甲基,从更有效且确实地发挥本实施方式的作用效果的观点出发,优选氢原子。另外,式(1)中,n1表示1以上的整数,n1的上限值通常为10,从对有机溶剂的溶解性的观点出发,优选1~3。
式(2)中,n2的平均值为1以上且30以下的范围。从更有效且确实地发挥本实施方式的作用效果的观点出发,n2以平均值计、优选7以上且30以下、更优选7以上且18以下。
式(3)中,R2各自独立地表示氢原子、甲基或乙基。
式(3)中,R3各自独立地表示氢原子或甲基。
另外,作为马来酰亚胺化合物,从对有机溶剂的溶解性和挠性的观点出发,更优选包含前述式(1)所示的马来酰亚胺化合物、同时含有选自由2,2- 双{4-(4-马来酰亚胺苯氧基)苯基}丙烷、前述式(2)所示的马来酰亚胺化合物、和前述式(3)所示的马来酰亚胺化合物组成的组中的至少1种马来酰亚胺化合物。
对于马来酰亚胺化合物,从均衡性良好地具有优异的助焊剂活性、优异的挠性、和低的热膨胀率的观点出发,相对于马来酰亚胺化合物的整体量100 质量份,优选含有前述式(1)所示的马来酰亚胺化合物5质量份以上且50质量份以下,优选含有前述式(2)所示的马来酰亚胺化合物5质量份以上且70 质量份以下,优选含有前述式(3)所示的马来酰亚胺化合物5质量份以上且 50质量份以下,优选含有2,2-双{4-(4-马来酰亚胺苯氧基)苯基}丙烷5质量份以上且50质量份以下。
马来酰亚胺化合物也可以以使马来酰亚胺化合物聚合而得到的预聚物、或使马来酰亚胺化合物与胺化合物等其他化合物聚合而得到的预聚物等的形式包含于树脂组合物。
马来酰亚胺化合物也可以使用市售的产品,例如可以举出大和化成工业株式会社制BMI-2300、K·I Chemical Industry Co.,LTD.制BMI-70、BMI-80、 BMI-1000P、BMI-650P、日本化药株式会社制MIR3000。
作为丙烯基化合物,例如可以举出丙烯基苯、丙烯基萘、丙烯基蒽、丙烯基苯酚、邻丙烯基苯氧基苯的一官能丙烯基化合物;双丙烯基苯醚、2,2- 双[4-(邻丙烯基苯氧基)苯基]丙烷、双[4-(邻丙烯基苯氧基)苯基]醚、双 [4-(邻丙烯基苯氧基)苯基]砜、4,4’-双(邻丙烯基苯氧基)二苯甲酮、2,2- 双[4-(邻丙烯基苯氧基)苯基]壬烷、2,2-双[3-叔丁基-4-(邻丙烯基苯氧基) 苯基]丙烷、2,2-双[3-仲丁基-4-(邻丙烯基苯氧基)苯基]丙烷、1,1-双[4-(邻丙烯基苯氧基)苯基]癸烷、1,1-双[2-甲基-4-(邻丙烯基苯氧基)-5-叔丁基苯基]-2-甲基丙烷、4,4’-环己叉基-双[1-(邻丙烯基苯氧基)-2-(1,1-二甲基乙基)苯]、4,4’-亚甲基-双[1-(邻丙烯基苯氧基)-2,6-双(1,1-二甲基乙基) 苯]、4,4’-亚甲基-双[1-(邻丙烯基苯氧基)-2,6-二-仲丁基苯]、4,4’-环己叉基 -双[1-(邻丙烯基苯氧基)-2-环己基苯]、4,4’-亚甲基-双[1-(邻丙烯基苯氧基)-2-壬基苯]、4,4’-(1-甲基乙叉基)-双[1-(邻丙烯基苯氧基)-2,6-双(1,1- 二甲基乙基)苯、4,4’-(2-乙基己叉基)-双[1-(邻丙烯基苯氧基)-苯]、4,4’- (1-甲基庚叉基)-双[1-(邻丙烯基苯氧基)-苯]、4,4’-环己叉基-双[1-(邻丙烯基苯氧基)-3-甲基苯]、2,2-双[4-(邻丙烯基苯氧基)苯基]-丙烷、2,2- 双[4-(邻丙烯基苯氧基)苯基]-六氟丙烷、2,2-双[3-甲基-4-(邻丙烯基苯氧基)苯基]-丙烷、2,2-双[3-甲基-4-(邻丙烯基苯氧基)苯基]-六氟丙烷、2,2- 双[3,5-二甲基-4-(邻丙烯基苯氧基)苯基]-丙烷、2,2-双[3,5-二甲基-4-(邻丙烯基苯氧基)苯基]-六氟丙烷、2,2-双[3-乙基-4-(邻丙烯基苯氧基)苯基]- 丙烷、2,2-双[3-乙基-4-(邻丙烯基苯氧基)苯基]-六氟丙烷、双[3-甲基-(邻丙烯基苯氧基)苯基]-甲烷、双[3,5-二甲基-(邻丙烯基苯氧基)苯基]-甲烷、双[3-乙基-(邻丙烯基苯氧基)苯基]-甲烷、3,8-双[4-(邻丙烯基苯氧基)苯基]-三环-[5,2,1,02·6]癸烷、4,8-双[4-(邻丙烯基苯氧基)苯基]-三环-[5,2,1,02·6]癸烷、3,9-双[4-(邻丙烯基苯氧基)苯基]-三环-[5,2,1,02·6]癸烷、4,9-双[4- (邻丙烯基苯氧基)苯基]-三环-[5,2,1,02·6]癸烷、1,8-双[4-(邻丙烯基苯氧基)苯基]-甲烷、1,8-双[3-甲基-4-(邻丙烯基苯氧基)苯基]-甲烷、1,8-双[3,5- 二甲基-4-(邻丙烯基苯氧基)苯基]-甲烷。
这些自由基聚合性化合物(C)可以单独使用1种或组合2种以上而使用。
〔I-4.无机填充材料(D)〕
为了改善耐燃性、改善导热率和降低热膨胀率,本实施方式的树脂组合物可以含有无机填充材料(D)。通过使用无机填充材料,可以改善树脂组合物等的耐燃性和导热率,降低热膨胀率。另外,如果无机填充材料(D)具有电绝缘性,则从更充分地确保芯片的电极间的电绝缘性的观点出发,将本实施方式的树脂组合物作为底部填充材料、优选作为预施底部填充材料的材料而使用的情况为优选。此处,“电绝缘性”是指,常温下的体积电阻率为1012Ω·cm以上。作为无机填充材料(D)的种类,没有特别限定,例如可以举出熔融二氧化硅等二氧化硅;勃姆石、氢氧化铝、氧化铝、和氮化铝等铝化合物;氧化镁、和氢氧化镁等镁化合物;碳酸钙、和硫酸钙等钙化合物;氧化钼、和钼酸锌等钼化合物;氮化硼;硫酸钡;天然滑石、和焙烧滑石等滑石;云母;短纤维状玻璃、球状玻璃、和微粉玻璃(例如E玻璃、T玻璃、 D玻璃)等玻璃。这些无机填充材料(D)可以单独使用1种或组合2种以上而使用。
这些之中,从改善树脂组合物的耐燃性、和降低热膨胀率的观点出发,作为无机填充材料(D),优选二氧化硅、氢氧化铝、氧化铝、勃姆石、氮化硼、氮化铝、氧化镁和氢氧化镁,更优选二氧化硅,其中,从提高填充性、底部填充材料对微细空间的流动性、和低热膨胀性的观点出发,进一步优选熔融二氧化硅。作为熔融二氧化硅,例如可以举出DenkaCorporation制的 SFP-120MC、SFP-130MC、Admatex Corporation制的SC1050-MLQ、SC2050-MNU、SC2050-MTX、SE2053-SQ、YA050C-MJF和YA050C-MJA。
无机填充材料(D)的平均粒径没有限定,将本发明的树脂组合物作为底部填充材料、优选作为预涂底部填充材料使用的情况下,从应对在芯片上排列的电极的窄间距化、电极间的窄间隙化的观点出发,优选3μm以下、更优选1μm以下。其平均粒径的下限值没有特别限定,例如可以为10nm。需要说明的是,本说明书中无机填充材料(D)的“平均粒径”是指,无机填充材料(D)的中值粒径。此处中值粒径是指,以某一粒径为基准,将粉体的粒度分布分成2部分的情况下,粒径较大一侧的颗粒的体积、和粒径较小一侧的颗粒的体积各占全部粉体50%的粒径。无机填充材料(D)的平均粒径 (中值粒径)通过湿式激光衍射·散射法而测定。
对于使用无机填充材料(D)时的树脂组合物中的含量,从改善树脂组合物的耐燃性和降低热膨胀率、且确保底部填充材料、优选预施底部填充材料的接合时的流动性的观点出发,相对于树脂组合物中的自由基聚合性化合物(C)的总计量100质量份,优选300质量份以下、更优选200质量份以下。另外,无机填充材料(D)的含量相对于树脂组合物中的自由基聚合性化合物(C)的总计量100质量份,优选设为10质量份以上、更优选设为20质量份以上、进一步优选设为50质量份以上。需要说明的是,组合使用2种以上的无机填充材料(D)的情况下,优选它们的总计量满足前述含量的范围。
〔I-5.挠性赋予成分(E)〕
本实施方式的树脂组合物中的挠性赋予成分(E)只要为能对含有树脂组合物的层赋予挠性的成分就没有特别限定,例如可以举出如聚酰亚胺、聚酰胺酰亚胺、聚苯乙烯、聚烯烃、苯乙烯-丁二烯橡胶(SBR)、异戊二烯橡胶(IR)、丁二烯橡胶(BR)、丙烯腈丁二烯橡胶(NBR)、聚氨酯、聚丙烯、 (甲基)丙烯酸类低聚物、(甲基)丙烯酸类聚合物、和有机硅树脂那样的热塑性的高分子化合物。这些挠性赋予成分(E)可以单独使用1种或组合2 种以上而使用。
这些之中,从对制造树脂组合物时使用的有机溶剂的溶解性、与马来酰亚胺化合物的相容性、树脂组合物的熔融粘度的控制性和挠性赋予的观点出发,作为挠性赋予成分(E),优选选自由(甲基)丙烯酸类低聚物和(甲基) 丙烯酸类聚合物组成的组中的至少1种。作为(甲基)丙烯酸类低聚物和(甲基)丙烯酸类聚合物,可以举出东亚合成株式会社的“ARUFON(注册商标)”系列、综研化学株式会社的“ACTFLOW(注册商标)”系列、根上工业株式会社的“PARACRON(注册商标)”系列、Kuraray Co.,Ltd.的“KURARITY (注册商标)”系列。
挠性赋予成分(E)的分子量没有限定,从对树脂组合物赋予挠性的观点出发,质均分子量优选1000以上,从赋予固化物的柔软性和良好的韧性的观点出发,更优选2000以上。另外,将树脂组合物作为底部填充材料、适合地作为预施底部填充材料使用的情况下,为了在金属接合部内不夹入树脂组合物、得到更良好且稳定的形状的接合,优选的是,将树脂组合物的熔融粘度控制为较低,确保接合时的树脂组合物的流动性。从这样的观点出发,挠性赋予成分(E)的质均分子量优选1000000以下、更优选800000以下、进一步优选100000以下,从溶剂溶解性的观点出发,进一步更优选10000以下。通过使用具有该优选的范围的质均分子量的挠性赋予成分(E),从而可以以更良好的均衡性兼顾树脂组合物的挠性、和作为底部填充材料、适合地作为预施底部填充材料使用时的接合性。
使用挠性赋予成分(E)的情况下,其在树脂组合物中的含量从熔融粘度的控制性的观点出发,相对于树脂组合物中的前述自由基聚合性化合物(C) 的总计量100质量份,优选设为100质量份以下、更优选设为50质量份以下、进一步优选设为30质量份以下。另外,挠性赋予成分(E)在树脂组合物中的含量从更有效且确实地发挥使用挠性赋予成分(E)所产生的作用效果的观点出发,相对于树脂组合物中的前述自由基聚合性化合物(C)的总计量100质量份,优选设为1质量份以上、更优选设为5质量份以上。需要说明的是,组合使用2种以上的挠性赋予成分(E)的情况下,优选它们的总计量为前述含量的范围内。
〔I-6.其他成分〕
本实施方式的树脂组合物包含具有酚性羟基的化合物(A)、金属离子捕捉剂(B)和自由基聚合性化合物(C),根据需要可以还包含无机填充材料 (D)、挠性赋予成分(E)、和1种或2种以上其他成分。
例如,为了改善吸湿耐热性、和改善芯片与树脂组合物的粘接性,本实施方式的树脂组合物可以包含硅烷偶联剂。作为硅烷偶联剂,只要为一般用于无机物的表面处理者、且与具有酚性羟基的化合物(A)的反应性低的硅烷偶联剂就没有限定。作为其具体例,可以举出乙烯基硅烷系硅烷偶联剂(例如乙烯基三甲氧基硅烷、γ-(甲基)丙烯酰氧基丙基三甲氧基硅烷)、苯基氨基硅烷系硅烷偶联剂(例如N-苯基-3-氨基丙基三甲氧基硅烷)、苯基硅烷系硅烷偶联剂、和咪唑硅烷系硅烷偶联剂。这些硅烷偶联剂可以单独使用1种或组合2种以上而使用。
使用硅烷偶联剂的情况下,其在树脂组合物中的含量没有限定。其中,从改善吸湿耐热性和降低倒装芯片安装时的挥发量的观点出发,其含量相对于树脂组合物中的前述自由基聚合性化合物(C)的总计量100质量份,优选 0.05质量份以上且20质量份以下、更优选0.1质量份以上且15质量份以下。需要说明的是,组合使用2种以上的硅烷偶联剂的情况下,优选它们的总计量为前述含量的范围内。
为了改善层叠体的制造性和改善无机填充材料(D)的分散性等,本实施方式的树脂组合物可以含有湿润分散剂。作为湿润分散剂,只要为一般用于涂料等的湿润分散剂就没有限定。例如可以举出BKY Japan株式会社制的 Disperbyk-110、Disperbyk-111、Disperbyk-180、Disperbyk-161、BYK-W996、 BYK-W9010、BYK-W903(以上为制品名)。这些湿润分散剂可以单独使用 1种或组合2种以上而使用。
使用湿润分散剂的情况下,其在树脂组合物中的含量没有限定,从改善层叠体的制造性的观点出发,相对于无机填充材料(D)100质量份,优选0.1 质量份以上且5质量份以下、更优选0.5质量份以上且3质量份以下。
使用湿润分散剂的情况下,树脂组合物中的其含量没有限定,从改善层叠体的制造性的观点出发,相对于树脂组合物中的前述自由基聚合性化合物 (C)的总计量100质量份,优选0.1质量份以上且5质量份以下、更优选0.5 质量份以上且3质量份。
需要说明的是,组合使用2种以上的湿润分散剂的情况下,优选它们的总计量为前述含量的范围内。
为了调整固化速度等,本实施方式的树脂组合物可以含有固化促进剂。作为固化促进剂,只要是作为马来酰亚胺化合物的固化促进剂公知的、一般使用者就没有特别限定。作为固化促进剂的具体例,可以举出咪唑类和其衍生物(例如2-乙基-4-甲基咪唑、2-苯基-4-甲基咪唑、1-苄基-2-苯基咪唑、2,4,5- 三苯基咪唑)、叔胺(例如三乙胺、三丁胺等)、以及作为热自由基聚合引发剂的各种有机过氧化物(例如过氧化二异丙苯、二(2-叔丁基过氧化异丙基) 苯、过氧化氢对薄荷烷、过氧化氢二异丙苯、氢过氧化枯烯)。这些固化促进剂可以单独使用1种或组合2种以上而使用。
使用固化促进剂的情况下,树脂组合物中的其含量没有特别限定,从调整固化速度的观点出发,相对于树脂组合物中的前述自由基聚合性化合物(C) 的总计量100质量份,优选0.001质量份以上且3质量份以下、更优选0.005质量份以上且2质量份以下、进一步优选0.01质量份以上且1质量份以下。需要说明的是,组合使用2种以上的固化促进剂的情况下,优选它们的总计量为前述含量的范围内。
本实施方式的树脂组合物中,在不有损期望的特性的范围内,根据各种目的,可以含有各种添加剂。作为添加剂,可以举出紫外线吸收剂、抗氧化剂、光聚合引发剂、荧光增白剂、光敏化剂、染料、颜料、增稠剂、润滑剂、消泡剂、流平剂、光泽剂和阻燃剂。这些添加剂可以单独使用1种或组合2种以上而使用。本实施方式的树脂组合物中,其他添加剂的含量没有特别限定,通常,相对于树脂组合物中的前述自由基聚合性化合物(C)的总计量100 质量份,分别为0.1质量份以上且10质量份以下。
本实施方式的树脂组合物由具有酚性羟基的化合物(A)、金属离子捕捉剂(B)和自由基聚合性化合物(C)制备,根据需要,将无机填充材料(D)、挠性赋予成分(E)、和其他成分进一步混合,从而可以制备。根据需要,也可以形成有机溶剂中溶解或分散有这些成分的清漆的形态。本实施方式的树脂组合物的清漆可以适合作为制作下述本实施方式的层叠体时的清漆使用。有机溶剂只要能使前述成分分别适合地溶解或分散、且不有损本实施方式的树脂组合物的期望的效果就没有限定。作为有机溶剂,例如可以举出甲醇、乙醇、和丙醇等醇类;丙酮、甲乙酮(以下,有时简记作“MEK”)、和甲基异丁基酮等酮类;二甲基乙酰胺、和二甲基甲酰胺等酰胺类;甲苯、和二甲苯等芳香族烃类。这些有机溶剂可以单独使用1种或组合2种以上而使用。
本实施方式的树脂组合物的助焊剂活性、挠性和保存稳定性优异。另外,通过将树脂组合物涂布于支撑基材上,从而可以提供具有助焊剂活性优异的树脂层的层叠体。在使用本实施方式的树脂组合物作为以层叠体的形态使用的预涂底部填充材料的情况下,助焊剂活性、挠性和保存稳定性优异,此外,还可以发挥接合性、吸湿耐热性、以及与芯片的粘接性也优异等其他适合的效果。如此,本实施方式的树脂组合物具有各种优异的特征,特别是可以以高的水平兼顾助焊剂活性、挠性和保存稳定性,因此,作为底部填充材料、特别是预施底部填充材料是极其有用的。
对于本实施方式的树脂组合物,在作为通过下述实施例中记载的方法评价助焊剂活性时的指标即焊料球的润湿铺展试验中,组合使用具有酚性羟基的化合物和金属离子捕捉剂时,从充分去除安装时的布线间的金属氧化膜的观点出发,优选组合在铜箔上熔融并润湿铺展的焊料球的接触角低于1.60弧度者。例如,将具有酚性羟基的化合物和金属离子捕捉剂散布于电解铜箔的光泽面,在其上设置焊料球,在热板上进行加热,在铜箔上使焊料熔融后,在室温下冷却。测定焊料球的接触角作为焊料球对铜箔的润湿铺展性,从而评价助焊剂活性。焊料球的接触角如下:求出在铜箔上熔融并润湿铺展的焊料球的半径(a)和焊料球的高度(b),根据下述式算出接触角。
焊料球的接触角=2arctan{(b)/(a)}
〔II.层叠体、使用层叠体制作的带树脂组合物层的半导体晶圆、使用层叠体制作的带树脂组合物层的半导体搭载用基板和半导体装置〕
本实施方式的层叠体、带树脂组合物层的半导体晶圆、带树脂组合物层的半导体搭载用基板、和半导体装置均使用前述本实施方式的树脂组合物而形成。
〔II-1.层叠体〕
本实施方式的层叠体具备:支撑基材;和,层叠于前述支撑基材上的含有本实施方式的树脂组合物的层。对于这样的层叠体,前述本实施方式的树脂组合物负载于支撑基材。作为支撑基材,没有特别限定,可以使用高分子薄膜。作为高分子薄膜的材质,例如可以举出:含有选自由聚氯乙烯、聚偏二氯乙烯、聚丁烯、聚丁二烯、聚氨酯、乙烯-氧化乙烯共聚物、聚对苯二甲酸乙二醇酯、聚萘二甲酸乙二醇酯和聚对苯二甲酸丁二醇酯的聚酯、聚乙烯、聚丙烯、乙烯-丙烯共聚物、聚甲基戊烯、聚酰亚胺和聚酰胺组成的组中的至少1种以上的树脂的薄膜、以及在这些薄膜的表面涂布有脱模剂的脱模薄膜。这些之中,特别优选聚酯、聚酰亚胺和聚酰胺,其中,更优选作为聚酯的1种的、聚对苯二甲酸乙二醇酯。
本实施方式的支撑基材的厚度没有限定,从层叠体的制造性、例如从将树脂组合物涂布于支撑基材时的涂布厚度的稳定性的观点出发,优选10μm 以上且100μm以下。另外,从树脂层叠体的输送性的观点出发,其厚度也优选10μm以上且100μm以下。作为厚度的下限,从确保制造层叠体时的成品率的方面出发,更优选12μm以上、进一步优选25μm以上、进一步更优选30μm 以上。另外,作为其厚度的上限,由于支撑基材不作为半导体装置的构成构件最终存在而是在工序中途被剥离,因此,从层叠体的制造成本的观点出发,更优选80μm以下。
作为在前述支撑基材上形成含有本实施方式的树脂组合物的层(以下,也简称为“树脂组合物层”)从而制造本实施方式的层叠体的方法,没有限定。作为这样的制造方法,例如可以举出下述方法:将有机溶剂中溶解或分散有本实施方式的树脂组合物的清漆涂布于前述支撑基材的表面,在加热和 /或减压下进行干燥,将溶剂去除,使本实施方式的树脂组合物固化,形成树脂组合物层。干燥条件没有特别限定,以相对于树脂组合物层的总量(100 质量%)、有机溶剂相对于树脂组合物层的含有比率通常成为10质量%以下、优选成为5质量%以下的方式使其干燥。达成上述干燥的条件也根据清漆中的有机溶剂的种类和配混量而不同。例如,相对于包含具有酚性羟基的化合物(A)、金属离子捕捉剂(B)和自由基聚合性化合物(C)的树脂组合物的它们的总计量100质量份,含有30质量份以上且60质量份以下的MEK的清漆的情况下,在1个气压下、在90℃以上且160℃以下的加热条件下进行1分钟以上且10分钟以下左右的干燥为标准。本实施方式的层叠体中的树脂组合物层的厚度没有限定,从树脂组合物层干燥时更良好地去除轻挥发成分的观点、和更有效且确实地发挥作为层叠体的功能的观点出发,优选5μm以上且 500μm以下的范围、更优选10μm以上且100μm以下的范围。
〔II-2.使用层叠体制作的带树脂组合物层的半导体晶圆、使用树脂层叠体制作的带树脂组合物层的半导体搭载用基板〕
本实施方式的带树脂组合物层的半导体晶圆具备:半导体晶圆;和,层叠于该半导体晶圆的前述层叠体中的树脂组合物层,其由前述本实施方式的层叠体和半导体晶圆形成。本实施方式的带树脂组合物层的半导体搭载用基板具备:半导体搭载用基板;和,层叠于该基板的前述层叠体中的树脂组合物层,其由前述本实施方式的层叠体和基板形成。
制作本实施方式的带有树脂组合物层的半导体晶圆的方法没有限定,例如,通过在半导体晶圆的形成有电极的面、即进行与基板的接合的面上,以与本实施方式的层叠体的树脂组合物层相对的方式进行粘贴从而得到。另外,制作本实施方式的带有树脂组合物层的基板的方法没有限定,例如,通过在基板的芯片搭载侧的面上,以与本实施方式的层叠体的树脂组合物层相对的方式进行粘贴从而得到。
作为使本实施方式的层叠体粘贴在半导体晶圆或基板上的方法,没有特别限定,可以适合使用真空加压式层压机。此时,优选如下方法:借助橡胶等弹性体对于本实施方式的层叠体进行加压并粘贴。作为层压条件,只要为本领域中一般使用的条件就没有特别限定,例如在50℃以上且140℃以下的温度、以1kgf/cm2以上且11kgf/cm2以下的范围的接触压力、以及20hPa以下的气氛减压下进行。层压工序后,通过利用金属板的热压,可以进行对粘贴而成的层叠体的平滑化。前述层压工序和平滑化工序可以通过市售的真空加压式层压机连续进行。对于粘附于半导体晶圆或基板的层叠体,在任意情况下均在芯片的倒装芯片安装前进行支撑基材的去除。
〔II-3.半导体装置〕
本实施方式的半导体装置例如具备:本实施方式的带有树脂组合物层的半导体晶圆、和/或本实施方式的带有树脂组合物层的基板,其是由本实施方式的树脂组合物层、芯片和基板构成的。制造本实施方式的半导体装置的方法没有限定,例如可以举出:对于本实施方式的带有树脂组合物层的半导体晶圆利用磨削的手段进行薄化和进行基于切割机的单片化,形成带有树脂组合物层的芯片,将其搭载于基板的方法等。另外,可以在本实施方式的带有树脂组合物层的基板上搭载芯片。在将带有树脂组合物层的芯片搭载于基板的方法和将半导体芯片搭载于带有树脂组合物层的基板的方法中,可以适当地使用与热压接工艺对应的倒装芯片键合机。另外,虽然本实施方式中,为了方便,对将芯片在基板上进行倒装芯片安装的情况进行了说明,但也可以在将芯片进行倒装芯片安装的同时应用本实施方式的树脂组合物的对象设为除基板以外的情况。例如,本实施方式的树脂组合物也可以用于将芯片搭载于半导体晶圆上时的半导体晶圆与芯片的接合部、经由TSV(硅通孔技术(Through Silicon Via))进行芯片间连接的芯片层叠体的各芯片间的接合部,在任意情况下,均可以得到基于本发明的优越性。
实施例
以下示出实施例和比较例,对本发明详细进行说明,但本发明不受这些实施例的任何限定。
[1.测定方法和助焊剂活性评价]
(1)质均分子量(Mw)
使用LC-20AD(商品名、株式会社岛津制作所制),通过凝胶渗透色谱 (GPC)法,作为标准聚苯乙烯换算分子量,测定质均分子量(Mw)。
(2)5%质量减少温度
称量约10mg的具有酚性羟基的化合物,用TG/DTA6200(商品名、SeikoInstruments Inc.制),在升温速度10℃/分钟的条件下从室温升温至500℃,得到的质量减少曲线中,将质量减少5%的温度作为5%质量减少温度。
(3)具有酚性羟基的化合物和金属离子捕捉剂的助焊剂活性评价
评价具有酚性羟基的化合物单独、金属离子捕捉剂单独、和组合使用具有酚性羟基的化合物与金属离子捕捉剂时的助焊剂活性。
<具有酚性羟基的化合物>
(I)PHENOLITE(注册商标)KA-1163(商品名、甲酚酚醛清漆型酚醛树脂、DIC株式会社制)
(II)TBIS(注册商标)-MP(商品名、双甲酚芴、田冈化学工业株式会社制)
(III)SN-495V(商品名、萘酚芳烷基型酚醛树脂、新日铁化学株式会社制)
(IV)BPN01(商品名、丙烯基亚联苯基树脂、群荣化学工业株式会社制)
(V)ELPC75(商品名、酚醛树脂、群荣化学工业株式会社制)
(VI)4,4’-亚甲基双(2,6-二-叔丁基苯酚)(东京化成工业株式会社制)
<金属离子捕捉剂>
(i)1-(4-叔丁基苯基)-3-(4-甲氧基苯基)-1,3-丙二酮(东京化成工业株式会社制)
(ii)(E,E)-1,7-双(4-羟基-3-甲氧基苯基)-1,6-庚二烯-3,5-二酮(东京化成工业株式会社制)
(iii)2,4-二氨基-6-甲基-1,3,5-三嗪(东京化成工业株式会社制)
(iv)2,2’-联吡啶(东京化成工业株式会社制)
(3-1)(I)~(VI)单独的助焊剂活性评价
将(I)~(VI)的具有酚性羟基的化合物散布于厚度12μm的电解铜箔 (3EC-III、商品名、三井金属矿业株式会社制)的光泽面,放置直径0.5mm 的焊料球(Ecosolder(注册商标)球M705(商品名)Sn-3.0Ag-0.5Cu合金、千住金属工业株式会社制)。将其在保持为235℃的热板上加热1分钟,在铜箔上使焊料熔融后,在室温下冷却。测定焊料球的接触角作为焊料球对铜箔的润湿铺展性,从而评价助焊剂活性。焊料球的接触角如下:使用数码显微镜(KH-7700(商品名)、HIROX CO.,LTD.制),求出在铜箔上熔融并润湿铺展的焊料球的半径(a)和焊料球的高度(b),根据下述式算出接触角。
焊料球的接触角=2arctan{(b)/(a)}
将焊料球的接触角低于1.60弧度的情况记作A、1.60弧度以上且低于2.00 弧度的情况记作B、2.00弧度以上的情况记作C。
[表1]
(I) | (II) | (III) | (IV) | (V) | (VI) | |
接触角 | C(2.33rad) | C(2.46rad) | C(2.31rad) | C(2.27rad) | C(2.45rad) | C(2.50rad) |
(3-2)(i)~(iv)单独的助焊剂活性评价
将(i)~(iv)的金属离子捕捉剂散布于厚度12μm的电解铜箔(3EC-III、商品名、三井金属矿业株式会社制)的光泽面,放置直径0.5mm的焊料球 (Ecosolder(注册商标)球M705(商品名)、Sn-3.0Ag-0.5Cu合金、千住金属工业株式会社制)。将其在保持为235℃的热板上加热1分钟,在铜箔上使焊料熔融后,在室温下冷却。测定焊料球的接触角作为焊料球对铜箔的润湿铺展性,从而评价助焊剂活性。焊料球的接触角如下:使用数码显微镜 (KH-7700(商品名)、HIROX CO.,LTD.制),求出在铜箔上熔融并润湿铺展的焊料球的半径(a)和焊料球的高度(b),根据下述式算出接触角。
焊料球的接触角=2arctan{(b)/(a)}
将焊料球的接触角低于1.60弧度的情况记作A、1.60弧度以上且低于2.00 弧度的情况记作B、2.00弧度以上的情况记作C。
[表2]
(i) | (ii) | (iii) | (iV) | |
接触角 | C(2.40rad) | C(2.34rad) | C(2.47rad) | C(2.42rad) |
(3-3)组合使用具有酚性羟基的化合物与金属离子捕捉剂时的助焊剂活性评价
将(I)~(VI)的具有酚性羟基的化合物和(i)~(iv)的金属离子捕捉剂散布于厚度12μm的电解铜箔(3EC-III、商品名、三井金属矿业株式会社制)的光泽面,放置直径0.5mmの焊料球(Ecosolder(注册商标)球M705 (商品名)、Sn-3.0Ag-0.5Cu合金、千住金属工业株式会社制)。将其在保持为235℃的热板上加热1分钟,在铜箔上使焊料熔融后,在室温下冷却。测定焊料球的接触角作为焊料球对铜箔的润湿铺展性,从而评价助焊剂活性。焊料球的接触角如下:使用数码显微镜(KH-7700(商品名)、HIROX CO.,LTD. 制),求出在铜箔上熔融并润湿铺展的焊料球的半径(a)和焊料球的高度(b),根据下述式算出接触角。
焊料球的接触角=2arctan{(b)/(a)}
将焊料球的接触角低于1.60弧度的情况记作AA、1.60弧度以上且低于 2.00弧度的情况记作A、2.00弧度以上的情况记作C。
[表3]
根据表1~3,对于(I)~(VI)的具有酚性羟基的化合物和(i)~(iv) 的金属离子捕捉剂各自单独的情况,焊料球未润湿铺展、即、无法确认良好的助焊剂活性。然而表明,组合使用(I)~(V)的具有酚性羟基的化合物和(i)~(iv)的金属离子捕捉剂时,体现良好的助焊剂活性。
[2.树脂组合物和树脂层叠体的制作]
(实施例1)
将作为具有酚性羟基的化合物(A)的PHENOLITE(注册商标)KA-1163 (商品名、质均分子量(Mw):4600、软化点:105~115℃、5%质量减少温度:298℃、甲酚酚醛清漆型酚醛树脂、DIC株式会社制)的MEK溶液(不挥发成分50质量%)60质量份(以不挥发成分换算计为30质量份)、作为金属离子捕捉剂(B)的1-(4-叔丁基苯基)-3-(4-甲氧基苯基)-1,3-丙二酮(东京化成工业株式会社制)30质量份、作为自由基聚合性化合物(C)的前述式(1)中的R1均为氢原子、n1为1~3的马来酰亚胺化合物(BMI-2300、大和化成工业株式会社制)的MEK溶液(不挥发成分50质量%)40质量份(以不挥发成分换算计为20质量份)、作为第2自由基聚合性化合物(C)的前述式 (2)所示的、n2为14(平均值)的马来酰亚胺化合物(BMI-1000P、K·IChemical Industry Co.,LTD.制)的MEK溶液(不挥发成分50质量%)40质量份(以不挥发成分换算计为20质量份)、作为第3自由基聚合性化合物(C)的双-(3- 乙基-5-甲基-4-马来酰亚胺苯基)甲烷(BMI-70、K·I Chemical Industry Co.,LTD.制)的MEK溶液(不挥发成分50质量%)60质量份(以不挥发成分换算计为30质量份)、进一步作为第4自由基聚合性化合物(C)的2,2-双{4- (4-马来酰亚胺苯氧基)苯基}丙烷(BMI-80、K·I Chemical IndustryCo.,LTD. 制)的MEK溶液(不挥发成分50质量%)60质量份(以不挥发成分换算计为 30质量份)、作为无机填充材料(D)的浆料二氧化硅(SC-1050MLQ、平均粒径:0.3μm、不挥发成分60质量%、株式会社Admatechs制)166.7质量份(以不挥发成分换算计为100质量份)、作为挠性赋予成分(E)的丙烯酸类聚合物(质均分子量(Mw):2900、ARUFON(注册商标)US-6170、东亚合成株式会社制)15质量份、作为咪唑系固化催化剂的1-苄基-2-甲基咪唑(东京化成工业株式会社制)的MEK溶液(不挥发成分20质量%)0.5质量份(以不挥发成分换算计为0.1质量份)进行混合,用高速搅拌装置搅拌30分钟,得到清漆。将该清漆涂布于表面上涂布有脱模剂的厚度38μm的聚对苯二甲酸乙二醇酯薄膜(TR1-38、UNITIKA LTD.制),以120℃加热干燥5分钟,得到本发明的树脂组合物层的厚度为30μm的树脂层叠体。
(实施例2)
作为具有酚性羟基的化合物(A),变更为TBIS(注册商标)-MP(商品名、9,9’-双-(4-羟基-3-甲基苯基)芴、分子量:378、熔点:225℃、5%质量减少温度:313℃、田冈化学工业株式会社制)的MEK溶液(不挥发成分 50质量%)60质量份(以不挥发成分换算计为30质量份),除此之外,与实施例1同样地制备清漆,得到树脂层叠体。
(实施例3)
作为金属离子捕捉剂(B),变更为(E,E’)-1,7-双(4-羟基-3-甲氧基苯基)-1,6-庚二烯-3,5-二酮(东京化成工业株式会社制)30质量份,除此之外,与实施例1同样地制备清漆,得到树脂层叠体。
(实施例4)
作为具有酚性羟基的化合物(A),变更为TBIS(注册商标)-MP(商品名、9,9’-双-(4-羟基-3-甲基苯基)芴、分子量:378、田冈化学工业株式会社制)的MEK溶液(不挥发成分50质量%)60质量份(以不挥发成分换算计为30质量份),作为金属离子捕捉剂(B),变更为(E,E)-1,7-双(4-羟基-3- 甲氧基苯基)-1,6-庚二烯-3,5-二酮(东京化成工业株式会社制)30质量份,除此之外,与实施例1同样地制备清漆,得到树脂层叠体。
(实施例5)
作为具有酚性羟基的化合物(A),变更为PHENOLITE(注册商标) KA-1163的MEK溶液(不挥发成分50质量%)100质量份(以不挥发成分换算计为50质量份),除此之外,与实施例1同样地制备清漆,得到树脂层叠体。
(实施例6)
作为金属离子捕捉剂(B),变更为1-(4-叔丁基苯基)-3-(4-甲氧基苯基)-1,3-丙二酮50质量份,除此之外,与实施例1同样地制备清漆,得到树脂层叠体。
(实施例7)
作为金属离子捕捉剂(B),变更为2,4-二氨基-6-甲基-1,3,5-三嗪(东京化成工业株式会社制)30质量份,除此之外,与实施例1同样地制备清漆,得到树脂层叠体。
(实施例8)
作为金属离子捕捉剂(B),变更为2,2’-联吡啶(东京化成工业株式会社制)30质量份,除此之外,与实施例1同样地制备清漆,得到树脂层叠体。
(比较例1)
不使用具有酚性羟基的化合物(A),除此之外,与实施例1同样地制备清漆,得到树脂层叠体。
(比较例2)
不使用金属离子捕捉剂(B),除此之外,与实施例1同样地制备清漆,得到树脂层叠体。
(比较例3)
不使用具有酚性羟基的化合物(A)和金属离子捕捉剂(B),除此之外,与实施例1同样地制备清漆,得到树脂层叠体。
[2.树脂层叠体和清漆的评价]
(1)安装试验
将实施例1~8和比较例1~3中得到的树脂层叠体切成8mm×8mm的正方形,并层压在评价用基板上后,用倒装芯片键合机(LFB-2301(商品名)、株式会社新川制),在台温度70℃、接合头温度300℃、载荷50N、时间8秒的条件下,将电极上具有由铜和焊料构成的Cu柱的半导体芯片压接,进行安装试验。通过安装试验样品的截面观察,在半导体芯片侧的Cu柱上的焊料与基板侧的铜布线的接触部,如果体现助焊剂活性、确认到合金生成,则记作AA、如果不体现助焊剂活性、无法确认到合金生成,则记作C。
(2)挠性
将实施例1~8和比较例1~3中得到的树脂层叠体裁切为5cm×10cm的条状后,在室温下,将支撑基材的聚对苯二甲酸乙二醇酯薄膜缠绕于外径为3cm 的金属管使其成为内侧,保持5秒后进行退卷。重复该作业10次后,以目视确认树脂组合物层的裂纹的有无,进行挠性的评价。将完全确认不到裂纹的发生的情况记作AA、稍确认到裂纹的发生但实际使用上对品质不造成影响的水平记作A、发生裂纹、实际使用上不允许的情况记作C。
(3)保存稳定性
用B型粘度计(东京计器株式会社制)测定实施例1~8和比较例1~3中得到的清漆的粘度(c),用B型粘度计再次测定在密闭容器内室温放置2周后的粘度(d)。以下述式算出经过2周后的粘度的变化率,将变化率低于20%的情况记作AA、经过2周后的粘度的变化率为20%以上且低于40%的情况记作 A、经过2周后的粘度的变化率为40%以上的情况记作C。
粘度的变化率={|(d)-(c)|/(c)}×100
[表4]
实施例1 | 实施例2 | 实施例3 | 实施例4 | 实施例5 | 实施例6 | 实施例7 | 实施例8 | 比较例1 | 比较例2 | 比较例3 | |
安装试验 | AA | AA | AA | AA | AA | AA | AA | AA | C | C | C |
挠性 | AA | AA | AA | AA | A | A | AA | AA | AA | AA | AA |
保存稳定性 | AA | AA | AA | AA | AA | AA | A | A | AA | AA | AA |
根据表4,使用本实施方式的树脂组合物的实施例1~8与比较例1~3相比,安装试验中体现良好的结果。另外,实施例5和6中记载的树脂组合物实用上没有问题,但根据实施例5和6的结果表明,本实施方式中,为了得到兼顾更优异的助焊剂活性和挠性的树脂组合物,需要具有酚性羟基的化合物和金属离子捕捉剂的配混量的最佳化。
另外,实施例7和8中记载的树脂组合物实用上没有问题,但实施例7和8 中使用的金属离子捕捉剂(B)与作为自由基聚合性化合物(C)配混的马来酰亚胺化合物显示反应性,因此,还表明在保存稳定性上有担心。另一方面,如果配混二酮衍生物作为金属离子捕捉剂(B),则与作为自由基聚合性化合物(C)配混的马来酰亚胺化合物不显示反应性,还表明可以得到良好的保存稳定性。
本申请基于2018年4月26日申请的日本专利申请(特愿2018-85651),将其内容作为参照引入至此。
产业上的可利用性
本发明的树脂组合物如前述,助焊剂活性、挠性和保存稳定性优异,发挥各种效果,因此,作为树脂组合物、特别是预施底部填充材料料是有用的。本发明的树脂组合物的助焊剂活性优异,因此,进行半导体芯片与基板的接合、半导体芯片与半导体晶圆的接合、进一步半导体芯片与半导体芯片的接合时,可以得到良好的接合状态,因此,是极其有用的。
Claims (24)
1.一种树脂组合物,其含有:
具有酚性羟基的化合物(A)、
金属离子捕捉剂(B)、和
自由基聚合性化合物(C),
所述金属离子捕捉剂(B)含有选自由胺类、胺衍生物、醚衍生物和酮衍生物组成的组中的至少1种,
所述树脂组合物中的所述具有酚性羟基的化合物(A)的含量相对于所述树脂组合物中的所述自由基聚合性化合物(C)的总计量100质量份为5质量份以上且50质量份以下,
所述树脂组合物中的所述金属离子捕捉剂(B)的含量相对于所述树脂组合物中的所述自由基聚合性化合物(C)的总计量100质量份为10质量份以上且50质量份以下。
2.根据权利要求1所述的树脂组合物,其中,所述具有酚性羟基的化合物(A)的分子量为200以上、且熔点为300℃以下。
3.根据权利要求1或2所述的树脂组合物,其中,所述具有酚性羟基的化合物(A)的5%质量减少温度为250℃以上。
4.根据权利要求1或2所述的树脂组合物,其中,所述金属离子捕捉剂(B)含有选自氮和氧中的至少1种元素作为配位原子。
5.根据权利要求1或2所述的树脂组合物,其中,所述金属离子捕捉剂(B)含有选自由三嗪衍生物、联吡啶衍生物和二酮衍生物组成的组中的至少1种。
6.根据权利要求1或2所述的树脂组合物,其中,所述金属离子捕捉剂(B)含有1,3-二酮。
7.根据权利要求1或2所述的树脂组合物,其中,所述金属离子捕捉剂(B)含有选自由2,4-二氨基-6-甲基-1,3,5-三嗪、2,2’-联吡啶、1,3-二苯基-1,3-丙二酮、1-(2-均三甲苯)-1,3-丁二酮、1,3-双(4-甲氧基苯基)-1,3-丙二酮、1-(4-叔丁基苯基)-3-(4-甲氧基苯基)-1,3-丙二酮、和(E,E)-1,7-双(4-羟基-3-甲氧基苯基)-1,6-庚二烯-3,5-二酮组成的组中的至少1种。
8.根据权利要求1或2所述的树脂组合物,其中,所述金属离子捕捉剂(B)含有选自由1-(4-叔丁基苯基)-3-(4-甲氧基苯基)-1,3-丙二酮、和(E,E)-1,7-双(4-羟基-3-甲氧基苯基)-1,6-庚二烯-3,5-二酮组成的组中的至少1种。
9.根据权利要求1或2所述的树脂组合物,其中,所述自由基聚合性化合物(C)含有选自由(甲基)丙烯酸酯化合物、马来酰亚胺化合物、和丙烯基化合物组成的组中的至少1种。
10.根据权利要求9所述的树脂组合物,其中,所述自由基聚合性化合物(C)含有选自由2,2’-双{4-(4-马来酰亚胺苯氧基)苯基}丙烷、1,2-双(马来酰亚胺)乙烷、1,4-双(马来酰亚胺)丁烷、1,6-双(马来酰亚胺)己烷、N,N’-1,3-亚苯基双马来酰亚胺、N,N’-1,4-亚苯基双马来酰亚胺、N-苯基马来酰亚胺、下述式(1)所示的马来酰亚胺化合物、下述式(2)所示的马来酰亚胺化合物和下述式(3)所示的马来酰亚胺化合物组成的组中的至少1种,
式(1)中,R1各自独立地表示氢原子或甲基,n1表示1以上的整数,
式(2)中,n2的平均值为1以上且30以下,
式(3)中,R2各自独立地表示氢原子、甲基或乙基,R3各自独立地表示氢原子或甲基。
11.根据权利要求10所述的树脂组合物,其中,所述自由基聚合性化合物(C)含有选自由2,2’-双{4-(4-马来酰亚胺苯氧基)苯基}丙烷、所述式(1)所示的马来酰亚胺化合物、所述式(2)所示的马来酰亚胺化合物和所述式(3)所示的马来酰亚胺化合物组成的组中的至少1种马来酰亚胺化合物。
12.根据权利要求1所述的树脂组合物,其还含有无机填充材料(D)。
13.根据权利要求12所述的树脂组合物,其中,所述无机填充材料(D)具有电绝缘性。
14.根据权利要求12或13所述的树脂组合物,其中,所述无机填充材料(D)的平均粒径为3μm以下。
15.根据权利要求12或13所述的树脂组合物,其中,所述无机填充材料(D)含有选自由二氧化硅、氢氧化铝、氧化铝、勃姆石、氮化硼、氮化铝、氧化镁和氢氧化镁组成的组中的至少1种。
16.根据权利要求12或13所述的树脂组合物,其中,所述树脂组合物中的所述无机填充材料(D)的含量相对于所述自由基聚合性化合物(C)的总计量100质量份为300质量份以下。
17.根据权利要求1所述的树脂组合物,其还含有挠性赋予成分(E)。
18.根据权利要求17所述的树脂组合物,其中,所述挠性赋予成分(E)含有热塑性的高分子化合物,所述高分子化合物的质均分子量为1000以上且1000000以下。
19.根据权利要求17或18所述的树脂组合物,其中,所述挠性赋予成分(E)含有选自由(甲基)丙烯酸类低聚物和(甲基)丙烯酸类聚合物组成的组中的至少1种。
20.根据权利要求1或2所述的树脂组合物,其用于预施底部填充材料。
21.一种层叠体,其具备:
支撑基材;和,
层叠于所述支撑基材上的含有权利要求1~20中任一项所述的树脂组合物的层。
22.一种带树脂组合物层的半导体晶圆,其具备:
半导体晶圆;和,
层叠于所述半导体晶圆的权利要求21所述的层叠体,
含有所述树脂组合物的层层叠于所述半导体晶圆。
23.一种带树脂组合物层的半导体搭载用基板,其具备:
半导体搭载用基板;和,
层叠于所述半导体搭载用基板的权利要求21所述的层叠体,
含有所述树脂组合物的层层叠于所述半导体搭载用基板。
24.一种半导体装置,其具备权利要求22所述的带树脂组合物层的半导体晶圆和/或权利要求23所述的带树脂组合物层的半导体搭载用基板。
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