CN1809917A - 用具有电子供体或受体官能团的噁唑啉衍生物将半导体模板粘结到基板上而制备的组合件 - Google Patents

用具有电子供体或受体官能团的噁唑啉衍生物将半导体模板粘结到基板上而制备的组合件 Download PDF

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Publication number
CN1809917A
CN1809917A CNA2004800169476A CN200480016947A CN1809917A CN 1809917 A CN1809917 A CN 1809917A CN A2004800169476 A CNA2004800169476 A CN A2004800169476A CN 200480016947 A CN200480016947 A CN 200480016947A CN 1809917 A CN1809917 A CN 1809917A
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China
Prior art keywords
functional group
electron donor
oxazoline
assembly
compound
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CNA2004800169476A
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English (en)
Inventor
O·M·穆萨
R·张
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National Starch and Chemical Investment Holding Corp
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National Starch and Chemical Investment Holding Corp
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Publication of CN1809917A publication Critical patent/CN1809917A/zh
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D263/14—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
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    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
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Abstract

一种用组合物将半导体模板粘结到基板上而制备的组合件，其中所述的组合物包含具有噁唑啉官能团及电子受体或电子供体官能团的化合物。电子供体官能团包括苯乙烯基、肉桂基和乙烯基醚基团。电子受体官能团包括马来酰亚胺、丙烯酸酯、富马酸和马来酸基。代表性的化合物具有(1)式结构。

Description

用具有电子供体或受体官能团的噁唑啉衍生物将半导体模板 粘结到基板上而制备的组合件
技术领域
本发明涉及用可固化的或固化的组合物将半导体模板粘结到基板上而制备的组合件，所述组合物包括具有噁唑啉官能团及电子受体或电子供体官能团的化合物。
背景技术
制造半导体包装件及微电子装置需要在装配工序中使用粘合剂和密封剂组合物。典型的组合物包括可自由基固化的组合物和电子供体/电子受体系统。这些组合物在某些用途中并非总能显示最佳性能，在半导体制造工业中仍然需要具有特定性能的材料。
发明概述
本发明的目的在于用组合物将半导体模板粘结到或负载在基板上而制成的组合件，所述组合物包含噁唑啉官能团及电子受体或电子供体官能团。该组合物以可固化的状态应用，并且是在原位被固化的。电子供体官能团包括苯乙烯基、肉桂基和乙烯基醚基团。电子受体官能团包括马来酰亚胺、丙烯酸酯、富马酸和马来酸基。
发明详述
噁唑啉是具有一个氮原子、一个氧原子和一个双键的五元杂环化合物。该双键可以位于三个位置之一上，因此，可能存在三种不同的噁唑啉环：2-噁唑啉(最常见)、3-噁唑啉和4-噁唑啉。噁唑啉发生阳离子开环均聚反应；电子供体/电子受体系统发生自由基聚合反应。因此，每分子具有至少一个噁唑啉基团及一个电子供体或电子受体官能团的化合物具有发生双重固化，即热固化和辐射固化的能力。
这里所用的组合物包括具有噁唑啉及电子供体或电子受体官能团的化合物、固化剂和填料。在那些存在电子受体官能团的组合物中，固化剂是任选的。组合物可以是通过混合或研磨制成的糊，或可以是通过本领域熟知的制备标准膜的技术制备的膜。
组合物主要由具有噁唑啉及电子供体或电子受体官能团的化合物组成；可替代地，对于一种或更多其他可固化树脂来说，具有噁唑啉及电子供体或电子受体官能团的化合物可以被用作粘合促进剂，其使用量可更少些。当用作粘合促进剂时，在组合物的用量将是有效量，并且占制剂重量的0.005至20.0％。
当用作粘合促进剂时，主要组分将是任何其他合适的可固化树脂，包括，例如，环氧、乙烯基醚、硫杂环戊烯、来自于肉桂基和苯乙烯基原料化合物的树脂、富马酸、马来酸、丙烯酸酯、马来酰亚胺、氰酸酯、氧杂环丁烷、酚、氨基树脂，炔丙基醚、苯并环丁烯和苯并噁嗪。
合适的固化剂为以有效量存在的用来固化组合物的热引发剂和光引发剂。通常，那些用量范围在0.1％至30％之间，优选为1％至20％，以该组合物中全部有机材料(即，不包括任何无机填料)的重量计。
优选的自由基引发剂包括过氧化物，如过氧化辛酸丁酯和过氧化二枯基，以及偶氮化合物，如2-2’偶氮双(2-甲基-丙腈)和2-2’偶氮双(2-甲基-丁腈)。优选的阳离子引发剂包括碘鎓、氧鎓、锍、氧化锍、各种其他的鎓盐。其他合适的阳离子引发剂包括路易斯酸催化剂和烷化剂，如芳基磺酸酯，例如对甲苯磺酸甲酯和三氟甲磺酸甲酯。优选的光引发剂系列为Ciba Specialty Chemicals以商标Irgacure或Rhodorsil2074出售的。在一些制剂中，同时使用热引发和光引发是理想的。固化过程可以开始于光的照射，之后用加热的方法完成，或开始于加热，之后用光的照射完成固化。
可固化的组合物将在60℃至250℃的温度范围内固化，并且固化作用在3秒到3小时的范围内发生。实际的固化曲线参数可以随化合物而变化，并且实际固化曲线参数能够由所属领域专业人员在不需要过多实验的情况下来确定。
适用的填料可以是导电性的或非导电性的。代表性的导电性填料为炭黑、石墨、金、银、铜、铂、钯、镍、铝、碳化硅、氮化硼、金刚石和矾土。代表性的非导电性的填料为蛭石、云母、硅灰石、碳酸钙、二氧化钛、砂、玻璃、熔凝硅石、煅制硅石、硫酸钡粒子以及卤代的乙烯聚合物，例如四氟乙烯、三氟乙烯、偏二氟乙烯、氟乙烯、偏二氯乙烯和氯乙烯。当存在填料时，其用量为制剂总重量的20％-90％。
这些组合物用于将半导体模板粘结到基板或在模板和基板之间作为底填料用于支持半导体模板。典型的基板是由金属，如铜、银、金、镍、合金(如42F/58Ni合金)、涂银的铜、或涂钯的铜制造的；由有机材料，如聚酰亚胺、聚酰胺或聚酯制造的；由陶瓷制造的；以及由复合材料或层压板(如印刷电路板)制造的。
在典型的模板粘结操作中，将以糊状或膜形式存在的粘合剂施用到基板上，如施用到铅框架(leadframe)的中央板上，在加热和压力条件下，硅模板与粘合剂接触。精确的工序和加工参数可以随不同的操作而发生变化。这些参数和工序是本领域熟知的，并且不意味着形成本发明的一部分。
在典型的填料操作中，用金属或聚合物焊料在模板上的电接点和在基板上对应的电接点之间进行连接。将焊料块放在基板的接点上，将接头对准，进行接触，将制得的组合件加热以回流焊料。在该模板和基板之间产生槽，将该槽用聚合的密封剂或底填料填充以强化这种互相连接。在填料工序中有一些变化，如底填料1密封可以在焊料回流后发生或与焊料回流同时发生。这些工序是本领域熟知的，并且不意味着形成本发明的一部分。
本发明的目的是用噁唑啉化合物作为模板粘结或底填料密封剂用于粘结或支持半导体模板到基板上。
可参考下面合成方案来设计噁唑啉化合物的各种合成路线。为了制备具有苯乙烯基及噁唑啉官能团的化合物，例如
Figure A20048001694700061
可应用根据A.Zerroukhi，A Ainser，A Arsac，N.Mignardhe和B.Marculescu，Polymer Bulletin，42，535，1999的方法。首先，让乙烯基苄基氯与氰化钠反应而得到乙烯苄基氰化物，然后，该乙烯苄基氰化物与乙醇胺反应而得到乙烯基苄基噁唑啉。
为了制备具有马来酰亚胺及噁唑啉官能团的的化合物，例如
让马来酐(在乙腈中)与6-氨基己酸(在乙酸中)反应而生成酰胺酸加合物。将该加合物脱水闭环而形成马来酰亚胺。该反应的方法是本领域公知的。然后，让该产物，即马来酰亚胺基己酸与2-(3-羟基-2-丙基)-2-噁唑啉(在甲苯中加热至80℃)在催化量的硫酸存在下进行反应，然后将产物分离。
为了制备具有月桂基及噁唑啉官能团的的化合物，例如
Figure A20048001694700072
将2-(3-羟基-2-丙基)-2-噁唑啉在过量的50％NaOH以及催化量的硫酸氢四丁铵中与肉桂酰氯在甲苯中开始在53℃，然后在75℃下反应数小时。将该反应物冷却到室温，并且萃取有机层，用盐水洗涤3次。将分离的有机层用MgSO4进行干燥，过滤，在真空下除去溶剂得到产物。
为了制备具有苯乙烯基及噁唑啉官能团的化合物，例如
将异氰酸3-异丙基-α，α-二甲基苄基酯(m-TMI)和2-(3-羟基-2-丙基)-2-噁唑啉溶解在甲苯中，在氮气中在催化量的二月桂酸二丁锡存在下在60℃下反应数小时。在将反应物冷却到室温后，真空除去溶剂得到产物。
为了制备具有丙烯酸基及噁唑啉官能团的的化合物，例如
Figure A20048001694700081
将2-(3-羟基-2-丙基)-2-噁唑啉在0℃下在干燥的二氯甲烷中与三乙胺进行混合。小心加入合适当量的溶解在干燥的二氯甲烷中的丙烯酰氯，并且使该混合物反应数小时。使溶剂蒸发，通过柱色谱法采用己烷/乙酸乙酯梯度纯化粗产物。
为了制备具有乙烯基醚及噁唑啉官能团的的化合物，例如
Figure A20048001694700082
将2-(3-羟基-2-丙基)-2-噁唑啉在过量的50％NaOH以及催化量的硫酸氢四丁铵中与2-氯乙基乙烯基醚在甲苯中开始在53℃，然后在75℃下反应数小时。将该反应冷却到室温，并且萃取有机层，用盐水洗涤3次。将分离的有机层用MgSO4进行干燥，过滤，在真空下除去溶剂得到产物。
为了制备具有马来酸及噁唑啉官能团的的化合物，例如
Figure A20048001694700083
将2-异丙烯基-2-噁唑啉与2-巯基乙醇在70℃下在甲苯中进行反应。将偶氮二异丁腈(AIBN)在甲苯中的溶液加入到该混合物中，该反应在70℃下连续进行数小时。减压除去溶剂制得2-异丙基-2-噁唑啉/2-巯基乙醇加合物。然后，让该2-异丙基-2-噁唑啉/2-巯基乙醇加合物与马来酐在氮气中在300mL的二甲氧基乙烷中在70℃下反应1小时。冷却后，将反应的内容物倒入庚烷中。将制得的产物在40℃下真空干燥24小时。

Claims (10)

1、一种用组合物将半导体模板粘结到基板上而制备的组合件，其中所述的组合物包含具有噁唑啉官能团及电子受体或电子供体官能团的化合物。
2、权利要求1的组合件，其中所述的电子供体官能团选自苯乙烯基、肉桂基和乙烯基醚。
3、权利要求1的组合件，其中所述的电子受体官能团选自马来酰亚胺、丙烯酸、富马酸和马来酸基。
4、权利要求1的组合件，其中所述的具有噁唑啉官能团及电子受体或电子供体官能团的化合物含有电子供体官能团并且具有下列结构
Figure A2004800169470002C1
5、权利要求1的组合件，其中所述的具有噁唑啉官能团及电子受体或电子供体官能团的化合物含有电子受体官能团并且具有下列结构
6、权利要求1的组合件，其中所述的具有噁唑啉官能团及电子受体或电子供体官能团的化合物含有电子供体官能团并且具有下列结构
Figure A2004800169470002C3
7、权利要求1的组合件，其中所述的具有噁唑啉官能团及电子受体或电子供体官能团的化合物含有电子供体官能团并且具有下列结构
8、权利要求1的组合件，其中所述的具有噁唑啉官能团及电子受体或电子供体官能团的化合物含有电子受体官能团并且具有下列结构
9、权利要求1的组合件，其中所述的具有噁唑啉官能团及电子受体或电子供体官能团的化合物含有电子供体官能团并且具有下列结构
10、权利要求1的组合件，其中所述的具有噁唑啉官能团及电子受体或电子供体官能团的化合物含有电子受体官能团并且具有下列结构
CNA2004800169476A 2004-02-17 2004-02-17 用具有电子供体或受体官能团的噁唑啉衍生物将半导体模板粘结到基板上而制备的组合件 Pending CN1809917A (zh)

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KR102182235B1 (ko) 2016-10-25 2020-11-24 애버리 데니슨 코포레이션 백본에 광개시제기를 갖는 블록 폴리머 및 접착제 조성물에서의 그것의 용도

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CN102325836B (zh) * 2009-02-19 2013-08-07 汉高公司 噁唑啉和/或噁嗪组合物

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