CN109642028A - 树脂组合物 - Google Patents
树脂组合物 Download PDFInfo
- Publication number
- CN109642028A CN109642028A CN201780053902.3A CN201780053902A CN109642028A CN 109642028 A CN109642028 A CN 109642028A CN 201780053902 A CN201780053902 A CN 201780053902A CN 109642028 A CN109642028 A CN 109642028A
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- CN
- China
- Prior art keywords
- resin
- resin combination
- acid
- general formula
- cured film
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000011347 resin Substances 0.000 title claims abstract description 271
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- 239000010949 copper Substances 0.000 claims description 41
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- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 28
- 239000000463 material Substances 0.000 claims description 26
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- 125000001118 alkylidene group Chemical group 0.000 claims description 13
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Classifications
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
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Abstract
树脂组合物,其特征在于,含有(a)树脂、(b)抗氧化剂、(d)交联剂,其中,上述(a)树脂包含选自聚酰亚胺前体、聚酰胺、聚酰亚胺、聚苯并噁唑、及它们的共聚物中的一种以上的树脂,上述(d)交联剂是在一分子中具有酚式羟基、并且在上述酚式羟基的两个邻位具有分子量为40以上的取代基的交联剂。提供树脂组合物,其可得到微细图案,且能够实现250℃以下的低温固化,同时可得到图案的面内均匀性优异、在可靠性评价(即实际使用的加速试验)后也具有高伸长率及与金属布线的高密合性的图案固化膜。
Description
技术领域
本发明涉及树脂组合物。更详细而言,涉及适合用于半导体元件等的表面保护膜、层间绝缘膜、有机电致发光元件的绝缘层等的树脂组合物。
背景技术
一直以来,耐热性、机械特性等优异的聚酰亚胺树脂、聚苯并噁唑树脂等被广泛用于电子设备的半导体元件的表面保护膜、层间绝缘膜等。将聚酰亚胺、聚苯并噁唑用作表面保护膜或层间绝缘膜时,通孔等的形成方法之一是使用正型光致抗蚀剂的蚀刻。但是,对于该方法而言,需要光致抗蚀剂的涂布、剥离工序,存在工序繁杂这样的问题。因此,出于使作业工序合理化的目的,对赋予了感光性的耐热性材料进行了研究。
对于聚酰亚胺、聚苯并噁唑而言,通常是将它们的前体的涂膜进行热脱水闭环,从而得到具有优异的耐热性及机械特性的薄膜。在该情况下,通常需要350℃左右的高温烧成。然而,例如有望成为下一代存储器的MRAM(Magnetoresistive Random Access Memory:磁阻存储器)、密封树脂不耐高温。因此,为了在这样的元件的表面保护膜、扇出型晶圆级封装(其在密封树脂上形成再布线结构)的层间绝缘膜中使用,谋求能够通过约250℃以下的低温烧成而固化、并能够获得不逊色于现有材料于350℃左右的高温进行烧成的情况下的、可靠性高的膜特性的聚酰亚胺树脂或聚苯并噁唑树脂。
另外,伴随高集成化、小型化及高速化的要求,近年来的半导体封装的布线向微细化发展。与此相伴,谋求在表面保护膜、层间绝缘膜等中也能够形成微细图案的感光性树脂组合物,但对于非感光性的树脂组合物、曝光部交联而导致不溶于显影液的负型感光性树脂组合物而言,无法形成微细图案,并且固化时的膜收缩大,因此存在面内均匀性差这样的课题。
另一方面,将耐热性树脂组合物用于半导体等用途时,加热固化后的膜会作为永久膜而残留在器件内。因此,加热固化后的膜的物性是重要的,在确认可靠性评价(即实际使用的加速试验)后的固化膜的物性(尤其是伸长率)满足要求规格的基础上,供于半导体封装。另外,作为半导体封装中的可靠性,与形成于半导体芯片表面的材料的密合性是重要的。特别是用于晶圆级封装的布线层间的绝缘膜等用途时,与电极、布线等中使用的金属材料的密合性是重要的。但是,对于包含上述可低温固化的树脂的树脂组合物而言,存在与用作这些布线材料的金属的密合性低的课题。特别在由能够形成微细图案的感光性树脂组合物形成的树脂固化膜的情况下,由于构成组合物的感光剂、敏化剂、产酸剂及溶解调节剂等添加物在加热固化后仍残留在固化膜中,因此,密合强度比不含添加物的情况低。
针对上述课题,公开了下述方案:通过向感光性树脂添加铜防变色剂从而抑制铜腐蚀的感光性树脂组合物(参见专利文献1);通过向具有脂肪族基团的聚苯并噁唑中添加杂环状化合物,从而可获得与铜的密合性、高伸长率的感光性树脂组合物(参见专利文献2)。另外,也进行了通过向聚酰亚胺树脂中加入抗氧化剂和环氧树脂从而提高伸长率的研究(参见专利文献3)。
现有技术文献
专利文献
专利文献1:日本特开2011-169980号公报
专利文献2:日本特开2010-96927号公报
专利文献3:日本特开2010-77382号公报
发明内容
发明要解决的课题
然而,对于向感光性树脂中添加铜防变色剂而得到的感光性树脂组合物的固化膜、向具有脂肪族基团的聚苯并噁唑中添加杂环状化合物而得到的感光性树脂组合物的固化膜而言,由于未适当组合使用交联剂和抗氧化剂,因此存在下述问题:固化膜的面内均匀性差,且高温保持试验、恒温高湿试验、热循环试验等可靠性评价后的伸长率低,并且从金属布线剥离。关于向聚酰亚胺树脂中加入抗氧化剂和环氧树脂而得到的树脂组合物,由于未使用合适的交联剂,因此也存在固化后的收缩大、膜厚·图案在面内不均匀、并且伸长率降低这样的问题,难以形成微细图案。
本发明是鉴于伴随上述现有技术的课题而作出的,提供下述树脂组合物,其可得到微细图案,且能够实现250℃以下的低温固化,同时可得到面内均匀性优异、在可靠性评价后也具有高伸长率及与金属布线的高密合性的图案固化膜。
用于解决课题的手段
为了解决上述课题,本发明将下述各构成作为特征。
[1]树脂组合物,其特征在于,含有(a)树脂、(b)抗氧化剂、(d)交联剂,其中,
上述(a)树脂包含选自聚酰亚胺前体、聚酰胺、聚酰亚胺、聚苯并噁唑、及它们的共聚物中的一种以上的树脂,
上述(d)交联剂是在一分子中具有酚式羟基、并且在上述酚式羟基的两个邻位具有分子量为40以上的取代基的交联剂。
[2]如[1]所述的树脂组合物,其中,上述(a)树脂为具有酚式羟基的碱溶性树脂,所述树脂组合物还含有(c)萘醌二叠氮化合物。
[3]如[1]或[2]所述的树脂组合物,其中,上述(d)交联剂是在一分子中具有3个以上酚式羟基的交联剂。
[4]如[1]~[3]中任一项所述的树脂组合物,其中,上述(b)抗氧化剂为具有受阻酚结构的抗氧化剂。
[5]如[1]~[4]中任一项所述的树脂组合物,其中,上述(b)抗氧化剂包含通式(1)表示的化合物。
[化学式1]
(通式(1)中,R1表示氢原子或碳原子数2以上的烷基,R2表示碳原子数2以上的亚烷基。A表示包含碳原子数2以上的亚烷基、O原子、及N原子中的至少任一者的1~4价有机基团。k表示1~4的整数。)
[6]如[1]~[5]中任一项所述的树脂组合物,其中,上述(a)树脂具有通式(2)表示的结构单元。
[化学式2]
(通式(2)中,R3~R6各自独立地表示碳原子数2~10的亚烷基,a、b、及c各自表示1≤a≤20、0≤b≤20、0≤c≤20的范围内的整数,重复单元的排列可以为嵌段式也可以为无规式。并且,通式(2)中,*表示化学键。)
[7]如[1]~[6]中任一项所述的树脂组合物,其中,
上述(a)树脂至少包含聚酰胺与聚酰亚胺的共聚物,
上述聚酰胺具有来自具有脂肪族基团的二胺的结构单元,并且,相对于所有的来自二胺的结构单元100摩尔%而言,上述来自具有脂肪族基团的二胺的结构单元的含量在5~40摩尔%的范围内。
[8]如[1]~[7]中任一项所述的树脂组合物,其中,
上述(a)树脂至少包含聚酰胺与聚酰亚胺的共聚物,
相对于上述聚酰胺与上述聚酰亚胺的结构单元合计100摩尔%而言,上述聚酰亚胺的结构单元的含量在2~50摩尔%的范围内。
[9]如[1]~[8]中任一项所述的树脂组合物,所述树脂组合物还含有(e)通式(3)表示的化合物,相对于上述(a)树脂100质量份而言,上述(e)通式(3)表示的化合物的含量在0.5~15质量份的范围内。
[化学式3]
(通式(3)中,R7~R9表示N原子、O原子或S原子中的任一者,R7~R9中的至少一个表示S原子。1表示0或1,m、n表示0~2的整数。R10~R12各自独立地表示氢原子或碳原子数1~20的有机基团。)
[10]如[1]~[9]中任一项所述的树脂组合物,所述树脂组合物还含有(f)具有下述通式(4)表示的结构单元的热交联剂。
[化学式4]
(通式(4)中,R13及R14各自独立地表示氢原子或甲基。R15为具有碳原子数2以上的亚烷基的2价有机基团,直链状、支链状、及环状均可。)
[11]树脂片材,其由[1]~[10]中任一项所述的树脂组合物形成。
[12]固化膜,其是将[1]~[10]中任一项所述的树脂组合物进行固化而得到的。
[13]固化膜,其是将[11]所述的树脂片材进行固化而得到的。
[14]如[12]或[13]所述的固化膜,所述固化膜的断裂点伸长率为50%以上。
[15]固化膜的浮凸图案的制造方法,其包括下述工序:
将[2]~[10]中任一项所述的树脂组合物涂布于基板上、或将权利要求11所述的树脂片材层压于基板上,并进行干燥而形成树脂膜的工序;
隔着掩模进行曝光的工序;
利用碱性溶液将照射部溶出或除去而进行显影的工序;及
对显影后的树脂膜进行加热处理的工序。
[16]如[15]所述的固化膜的浮凸图案的制造方法,其中,将上述树脂组合物涂布于基板上并进行干燥而形成树脂膜的工序包括使用狭缝喷嘴涂布于基板上的工序。
[17]半导体电子部件或半导体器件,其配置有[12]~[14]中任一项所述的固化膜作为铜金属的再布线间的层间绝缘膜。
[18]如[17]所述的半导体电子部件或半导体器件,其中,上述再布线由经氧化处理的铜金属布线构成。
[19]如[17]或[18]所述的半导体电子部件或半导体器件,其中,上述再布线为铜金属布线,铜金属布线的宽度及相邻布线彼此的间隔为5μm以下。
[20]半导体电子部件或半导体器件,其在配置有硅芯片的密封树脂基板上配置有[12]~[14]中任一项所述的固化膜作为再布线间的层间绝缘膜。
[21]如[17]~[20]所述的半导体电子部件或半导体器件,其中,上述再布线为铜金属布线,并且,介由凸块将半导体芯片与铜金属布线连接。
[22]如[17]~[21]所述的半导体电子部件或半导体器件,其中,随着[17]中记载的再布线层接近半导体芯片,金属布线的宽度及相邻布线彼此的间隔变窄。
[23]如[17]~[22]所述的半导体电子部件或半导体器件,其中,[17]中记载的层间绝缘膜的厚度随着接近半导体芯片而变薄。
[24]有机EL显示装置,其具备[12]~[14]中任一项所述的固化膜。
[25]半导体电子部件或半导体器件的制造方法,其包括下述工序:
在配置有临时粘贴材料的支承基板上配置[12]~[14]中任一项所述的固化膜作为再布线间的层间绝缘膜的工序;
在层间绝缘膜上配置硅芯片和密封树脂的工序;以及
然后,将配置有临时粘贴材料的支承基板与再布线进行剥离的工序。
发明的效果
提供下述树脂组合物,其可得到微细图案,且能够实现250℃以下的低温固化,同时可得到面内均匀性优异、在可靠性评价后也具有高伸长率及与金属布线的高密合性的图案固化膜。
附图说明
[图1]为示出具有凸块的半导体器件的焊盘部分的放大截面的图。
[图2]为示出具有凸块的半导体器件的详细制作方法的图。
[图3]为示出本发明的实施例的半焊盘部分的放大截面图。
[图4]为示出本发明的实施例的感应器装置的线圈部件的截面图。
[图5]为示出RDL-First中的半导体器件制作方法的图。
[图6]为TFT基板的一例的截面图。
具体实施方式
本发明的树脂组合物的特征在于,其含有(a)树脂、(b)抗氧化剂、(d)交联剂,其中,
上述(a)树脂包含选自聚酰亚胺前体、聚酰胺、聚酰亚胺、聚苯并噁唑、及它们的共聚物中的一种以上的树脂,
上述(d)交联剂是在一分子中具有酚式羟基、并且在上述酚式羟基的两个邻位具有分子量为40以上的取代基的交联剂。
本发明的树脂组合物通过适当地使用(b)抗氧化剂和(d)交联剂,可得到微细图案,且能够实现250℃以下的低温固化,同时能够得到面内均匀性优异、在可靠性评价后也具有高伸长率及与金属布线的高密合性的图案固化膜。
另外,在上述(a)树脂为具有酚式羟基的碱溶性树脂、且所述树脂组合物还含有(c)萘醌二叠氮化合物的情况下,可进一步得到微细图案,并且能够省略繁杂的工序,能够实现作业的合理化,是优选的。
本发明中,所谓碱溶性树脂,是指溶解于四甲基氢氧化铵、胆碱、三乙胺、二甲基氨基吡啶、单乙醇胺、二乙基氨基乙醇、氢氧化钠、氢氧化钾、碳酸钠等的碱性水溶液中的树脂。
上述聚酰胺结构是两组氨基和羟基彼此位于邻位的苯并噁唑前体、其他聚羟基酰胺、聚酰胺、或它们的共聚结构。另外,上述聚酰亚胺前体结构是聚酰胺酸、聚酰胺酸酯、用酰胺酸及/或酰胺酸酯对树脂末端、树脂侧链进行封端而成的结构。
另外,上述(a)树脂优选具有通式(2)表示的结构单元。
[化学式5]
(通式(2)中,R3~R6各自独立地表示碳原子数2~10的亚烷基,a、b、及c各自表示1≤a≤20、0≤b≤20、0≤c≤20的范围内的整数,重复单元的排列可以为嵌段式也可以为无规式。并且,通式(2)中,*表示化学键。)
通式(2)表示的结构单元中,通过醚基所具有的伸缩性,在制成固化膜时能够赋予高伸长率性。另外,通过上述醚基的存在,能够与金属形成络合物、形成氢键,能够得到与金属的高密合性。
此外,优选地,上述(a)树脂至少包含聚酰胺与聚酰亚胺的共聚物,上述聚酰胺具有来自具有脂肪族基团的二胺的结构单元,并且,相对于所有的来自二胺的结构单元100摩尔%而言,来自具有脂肪族基团的二胺的结构单元的含量在5~40摩尔%的范围内。
本发明中,具有脂肪族基团的二胺残基优选包含于上述聚酰胺结构、酰亚胺前体及聚酰亚胺中的至少任一结构中。可以包含于任一结构中,也可以包含于全部结构中,包含于聚酰胺结构中时,金属密合和高伸长率化的效果高,因此优选。另外,通过相对于所有的来自二胺的结构单元100摩尔%而言以5摩尔%以上的含量含有来自具有脂肪族基团的二胺的结构单元,可获得由具有脂肪族基团的二胺残基所带来的高金属密合效果,另外,通过含有40摩尔%以下,不易发生脂肪族基团的氧化劣化,因此能够防止从金属基板剥离,得到具有高可靠性的固化膜,因此优选。
另外,通过具有聚酰亚胺结构,与聚酰胺结构单体的情况相比,能够提高与金属的相互作用,使制成固化膜时与金属的密合性提高。
此外,相对于上述(a)树脂的上述聚酰胺与上述聚酰亚胺的结构单元合计100摩尔%而言,上述聚酰亚胺的结构单元的含量优选在2~50摩尔%的范围内。通过具有2摩尔%以上的聚酰亚胺结构,与聚酰胺结构单体的情况相比,能够提高与金属的相互作用,使制成固化膜时与金属的密合性提高,为50%摩尔%以下时,能够得到由聚酰胺带来的高伸长率性,因此优选。
本发明中,上述(a)树脂优选为下述树脂:上述聚酰胺为通式(5)表示的结构,上述聚酰亚胺前体及聚酰亚胺具有选自通式(6)及通式(7)表示的结构中的至少一种以上的结构,上述聚苯并噁唑具有通式(8)表示的结构。
[化学式6]
(通式(5)~(8)中,X1表示2~6价有机基团,X2及X3各自独立地表示4~10价有机基团,X4表示2~6价有机基团,Y1~Y3各自独立地表示2~4价有机基团,Y4表示4~6价有机基团,R表示氢原子或碳原子数1~20的有机基团。p、q、r、s、t、u、v、w各自独立地为0~4的整数。
上述通式(5)中,X1、X4表示碳原子数2以上的2价~6价有机基团,表示酸的结构成分。X1、X4为来自下述化合物的结构:对苯二甲酸、间苯二甲酸、二苯基醚二甲酸、萘二甲酸、双(羧基苯基)丙烷等芳香族二羧酸;环丁烷二甲酸、环己烷二甲酸、丙二酸、二甲基丙二酸、乙基丙二酸、异丙基丙二酸、二正丁基丙二酸、丁二酸、四氟丁二酸、甲基丁二酸、2,2-二甲基丁二酸、2,3-二甲基丁二酸、二甲基甲基丁二酸、戊二酸、六氟戊二酸、2-甲基戊二酸、3-甲基戊二酸、2,2-二甲基戊二酸、3,3-二甲基戊二酸、3-乙基-3-甲基戊二酸、己二酸、八氟己二酸、3-甲基己二酸、八氟己二酸、庚二酸、2,2,6,6-四甲基庚二酸、辛二酸、十二氟辛二酸、壬二酸、癸二酸、十六氟癸二酸、1,9-壬二酸、十二烷二酸、十三烷二酸、十四烷二酸、十五烷二酸、十六烷二酸、十七烷二酸、十八烷二酸、十九烷二酸、二十烷二酸、二十一烷二酸、二十二烷二酸、二十三烷二酸、二十四烷二酸、二十五烷二酸、二十六烷二酸、二十七烷二酸、二十八烷二酸、二十九烷二酸、三十烷二酸、三十一烷二酸、三十二烷二酸、二甘醇酸等脂肪族二羧酸;以及下述通式所示的二羧酸;偏苯三甲酸、均苯三甲酸等三羧酸;这些酸的芳香族环、烃上的一部分氢原子被碳原子数1~10的烷基、氟烷基、卤原子等取代而成的化合物;包含-S-、-SO-、-SO2-、-NH-、-NCH3-、-N(CH2CH3)-、-N(CH2CH2CH3)-、-N(CH(CH3)2)-、-COO-、-CONH-、-OCONH-、或-NHCONH-等键的化合物。
[化学式7]
其中,就X1、X4来自具有芳香族的二羧酸的结构而言,由于在热固化时不易发生闭环,因此可抑制由膜收缩导致的应力上升,能够提高密合性,因此优选。
制造树脂时,在进行缩聚时可使用例如以下述通式所示那样的活性羧酸基替换X1、X4的羧酸基而成的化合物。
[化学式8]
式中,B及C各自独立地可举出氢原子、甲基、乙基、丙基、异丙基、叔丁基、三氟甲基、卤基、苯氧基、硝基等,但并不限定于此。
其中,优选使用除氯化物以外的活性羧酸基。通过使用除氯化物以外的活性羧酸基,从而能够减少所得树脂中的氯离子,防止因存在氯离子而引起的从金属基板上剥离。另外,作为活性羧酸基,进一步优选使用二咪唑(diimidazolide)化合物。由于二咪唑化合物的离去基团会成为水溶性的咪唑,因此能够用水来进行所得的树脂的再沉淀、洗涤。进而,由于离去的咪唑为碱性,因此在聚合时作为聚酰亚胺前体结构的闭环促进剂发挥作用,能够在制造聚酰胺树脂的阶段提高酰亚胺化的闭环率。结果,能够降低通过热处理制作固化膜时的闭环率。
通式(5)~(7)中的Y1~Y3表示2价~4价有机基团,Y4表示4~6价有机基团,表示来自二胺的有机基团。
通式(5)~(7)中的Y1~Y4优选包含具有酚式羟基的二胺残基。通过包含具有酚式羟基的二胺残基,树脂可获得在碱性显影液中的适度溶解性,因此可得到曝光部与未曝光部的高对比度,能够形成期望的图案。
作为具有酚式羟基的二胺的具体例,例如可举出双(3-氨基-4-羟基苯基)六氟丙烷、双(3-氨基-4-羟基苯基)砜、双(3-氨基-4-羟基苯基)丙烷、双(3-氨基-4-羟基苯基)甲烷、双(3-氨基-4-羟基苯基)醚、双(3-氨基-4-羟基)联苯、2,2’-二(三氟甲基)-5,5’-二羟基-4,4’-二氨基联苯、双(3-氨基-4-羟基苯基)芴、2,2’-双(三氟甲基)-5,5’-二羟基联苯胺等芳香族二胺、它们的芳香族环、烃的一部分氢原子被碳原子数1~10的烷基、氟烷基、卤原子等取代而得到的化合物、以及具有如下所示的结构的二胺等,但并不限定于此。用于共聚的其他二胺可以直接使用,或者以对应的二异氰酸酯化合物、三甲基甲硅烷基化二胺的形式使用。另外,可以组合这些中的两种以上二胺成分而使用。
[化学式9]
[化学式10]
Y1~Y4可以包含除上述以外的具有芳香族的二胺残基。通过将它们共聚,能够提高耐热性。作为具有芳香族的二胺残基的具体例,可举出3,4’-二氨基二苯基醚、4,4’-二氨基二苯基醚、3,4’-二氨基二苯基甲烷、4,4’-二氨基二苯基甲烷、3,4’-二氨基二苯基砜、4,4’-二氨基二苯基砜、3,4’-二氨基二苯基硫醚、4,4’-二氨基二苯基硫醚、1,4-双(4-氨基苯氧基)苯、联苯胺、间苯二胺、对苯二胺、1,5-萘二胺、2,6-萘二胺、双(4-氨基苯氧基苯基)砜、双(3-氨基苯氧基苯基)砜、双(4-氨基苯氧基)联苯、双{4-(4-氨基苯氧基)苯基}醚、1,4-双(4-氨基苯氧基)苯、2,2’-二甲基-4,4’-二氨基联苯、2,2’-二乙基-4,4’-二氨基联苯、3,3’-二甲基-4,4’-二氨基联苯、3,3’-二乙基-4,4’-二氨基联苯、2,2’,3,3’-四甲基-4,4’-二氨基联苯、3,3’,4,4’-四甲基-4,4’-二氨基联苯、2,2’-双(三氟甲基)-4,4’-二氨基联苯等芳香族二胺、它们的芳香族环、烃的一部分氢原子被碳原子数1~10的烷基、氟烷基、卤原子等取代而得到的化合物等,但并不限定于此。用于共聚的其他二胺可以直接使用,或者以对应的二异氰酸酯化合物、三甲基甲硅烷基化二胺的形式使用。另外,可以组合这些中的两种以上二胺成分而使用。
另外,Y1~Y4优选包含具有脂肪族基团的二胺残基。具有脂肪族基团的二胺残基与金属的亲和性高,因此能够形成金属密合性高的树脂。另外,脂肪族二胺的碱性高,因此在聚合时作为闭环促进剂发挥作用,由此能够在制造聚酰胺树脂的阶段提高酰亚胺骨架的闭环率。结果,能够降低热固化时的闭环率,能够对固化膜的收缩以及由此产生的固化膜的应力上升进行抑制。由此,能够抑制由应力引起的密合力降低。此外,柔软的脂肪族二胺残基有助于聚酰胺的高伸长率化,因此能够提高与金属的密合性,得到具有低应力性、高伸长率性的固化膜。
本发明中,含有脂肪族基团的二胺优选具有烷基及烷基醚基中的至少任一种有机基团。具体而言,为选自烷基、环烷基、烷基醚基、环烷基醚基中的至少一种的二胺,且它们的烃的一部分氢原子也可以被碳原子数1~10的烷基、氟烷基、卤原子等取代,还可以包含-S-、-SO-、-SO2-、-NH-、-NCH3-、-N(CH2CH3)-、-N(CH2CH2CH3)-、-N(CH(CH3)2)-、-COO-、-CONH-、-OCONH-、或-NHCONH-等键,另外,这些有机基团也可以具有不饱和键、脂环结构。
另外,本发明中,称作具有脂肪族基团的二胺的情况下,是指不含硅氧烷结构的二胺。其原因在于,二胺中具有硅氧烷结构时,虽然可提高与硅基板的密合性,但本发明的目的即赋予高伸长率性、高金属密合性的效果差。出于提高与硅基板的密合性的目的而含有硅氧烷结构时,如本发明中后文所述,可使通式(5)~(8)中的Y1~Y4含有硅氧烷结构。
作为具有脂肪族基团的二胺的具体化合物,可举出乙二胺、1,3-二氨基丙烷、2-甲基-1,3-丙二胺、1,4-二氨基丁烷、1,5-二氨基戊烷、2-甲基-1,5-二氨基戊烷、1,6-二氨基己烷、1,7-二氨基庚烷、1,8-二氨基辛烷、1,9-二氨基壬烷、1,10-二氨基癸烷、1,11-二氨基十一烷、1,12-二氨基十二烷、1,2-环己二胺、1,3-环己二胺、1,4-环己二胺、1,2-双(氨基甲基)环己烷、1,3-双(氨基甲基)环己烷、1,4-双(氨基甲基)环己烷、4,4’-亚甲基双(环己胺)、4,4’-亚甲基双(2-甲基环己胺)、1,2-双(2-氨基乙氧基)乙烷、KH-511、ED-600、ED-900、ED-2003、EDR-148、EDR-176、D-200、D-400、D-2000、THF-100、THF-140、THF-170、RE-600、RE-900、RE-2000、RP-405、RP-409、RP-2005、RP-2009、RT-1000、HE-1000、HT-1100、HT-1700(以上为商品名,HUNTSMAN(株)制)、以及以下的化合物,它们的芳香族环、烃的一部分氢原子也可以被碳原子数1~10的烷基、氟烷基、卤原子等取代,还可以包含-S-、-SO-、-SO2-、-NH-、-NCH3-、-N(CH2CH3)-、-N(CH2CH2CH3)-、-N(CH(CH3)2)-、-COO-、-CONH-、-OCONH-、或-NHCONH-等键。
[化学式11]
(式中n为1~20的整数。)
本发明中,具有脂肪族基团的二胺是具有选自烷基、及烷基醚基中的至少一种有机基团、且它们的结构是主链为直链的非环化结构时,可得到柔软性及伸缩性,在制成固化膜时能够实现低应力化、高伸长率化,因此优选。
另外,具有脂肪族基团的二胺残基进一步优选具有通式(2)表示的结构单元。
[化学式12]
(通式(2)中,R3~R6各自独立地表示碳原子数2~10的亚烷基,a、b、c各自表示1≤a≤20、0≤b≤20、0≤c≤20的范围内的整数,重复单元的排列可以为嵌段式或无规式。通式(2)中,*表示化学键。)
通式(2)表示的结构单元中,通过醚基所具有的伸缩性,可以在制成固化膜时赋予高伸长率性。另外,通过上述醚基的存在,能够与金属形成络合物、形成氢键,能够得到与金属的高密合性。
作为具有通式(2)表示的结构单元的化合物,可举出1,2-双(2-氨基乙氧基)乙烷、KH-511、ED-600、ED-900、ED-2003、EDR-148、EDR-176、D-200、D-400、D-2000、THF-100、THF-140、THF-170、RE-600、RE-900、RE-2000、RP-405、RP-409、RP-2005、RP-2009、RT-1000、HE-1000、HT-1100、HT-1700(以上为商品名,HUNTSMAN(株)制)、下式所示的化合物,它们的芳香族环、烃的一部分氢原子也可以被碳原子数1~10的烷基、氟烷基、卤原子等取代,可以包含-S-、-SO-、-SO2-、-NH-、-NCH3-、-N(CH2CH3)-、-N(CH2CH2CH3)-、-N(CH(CH3)2)-、-COO-、-CONH-、-OCONH-、或-NHCONH-等键,但并不限定于这些。
[化学式13]
(式中n为1~20的整数。)
另外,通式(2)表示的结构单元的数均分子量优选为150以上且2,000以下。由于可获得柔软性及伸缩性,因此通式(2)表示的结构单元的数均分子量优选为150以上,更优选为600以上,进一步优选为900以上。另外,由于能够维持在碱性溶液中的溶解性,因此通式(2)表示的结构单元的数均分子量优选为2,000以下,更优选为1,800以下,进一步优选为1,500以下。
另外,在烷基醚中,四亚甲基醚基由于耐热性优异,因此可赋予可靠性评价后的金属密合性,因此优选。作为例子,可举出RT-1000、HE-1000、HT-1100、HT-1700(以上为商品名,HUNTSMAN(株)制)等,但并不限定于这些。
另外,具有脂肪族基团的二胺优选为不具有芳香族基团的结构。通过不具有芳香族基团,从而能够赋予充分的柔软性,因此能够赋予高伸长率性。
通过使用这样的具有脂肪族基团的二胺,可以维持在碱性溶液中的溶解性,同时能够对得到的固化膜赋予低应力性、高伸长率性、及高金属密合性。
本发明中,具有脂肪族基团的二胺残基在全部二胺残基中的含量优选为5~40摩尔%。通过含有5摩尔%以上,可获得由具有脂肪族基团的二胺残基带来的高金属密合的效果,另外,通过含有40摩尔%以下,树脂的吸湿性降低,因此能够防止从金属基板剥离,能够得到具有高可靠性的固化膜,因此优选。
具有脂肪族基团的二胺残基的重复单元的排列可以为嵌段式或无规式,但由于除了能够对聚酰胺结构赋予高金属密合性和低应力化以外,还会提高伸长率,因此优选包含于通式(5)表示的聚酰胺结构中。
进而,为了使得与硅基板的密合性提高,通式(5)~(7)中的Y1~Y3也可以共聚具有硅氧烷结构的脂肪族基团。具体而言,作为二胺成分,可举出共聚有1~10摩尔%的双(3-氨基丙基)四甲基二硅氧烷、双(对氨基苯基)八甲基五硅氧烷等的二胺成分等。
另外,在作为聚酰亚胺前体结构的上述通式(6)、作为聚酰亚胺结构的通式(7)中,X2~X3表示酸二酐的残基,且为4价~10价有机基团。
作为上述酸二酐,具体而言,可举出均苯四甲酸二酐、3,3’,4,4’-联苯四甲酸二酐、2,3,3’,4’-联苯四甲酸二酐、2,2’,3,3’-联苯四甲酸二酐、3,3’,4,4’-二苯甲酮四甲酸二酐、2,2’,3,3’-二苯甲酮四甲酸二酐、2,2-双(3,4-二羧基苯基)丙烷二酐、2,2-双(2,3-二羧基苯基)丙烷二酐、1,1-双(3,4-二羧基苯基)乙烷二酐、1,1-双(2,3-二羧基苯基)乙烷二酐、双(3,4-二羧基苯基)甲烷二酐、双(2,3-二羧基苯基)甲烷二酐、双(3,4-二羧基苯基)砜二酐、双(3,4-二羧基苯基)醚二酐、1,2,5,6-萘四甲酸二酐、9,9-双(3,4-二羧基苯基)芴酸二酐、9,9-双{4-(3,4-二羧基苯氧基)苯基}芴酸二酐、2,3,6,7-萘四甲酸二酐、2,3,5,6-吡啶四甲酸二酐、3,4,9,10-苝四甲酸二酐、2,2-双(3,4-二羧基苯基)六氟丙烷二酐等芳香族四羧酸二酐、3,3’,4,4’-二苯基砜四甲酸二酐、1,2,3,4-环丁烷四甲酸二酐、1,2,3,4-环戊烷四甲酸二酐、1,2,4,5-环己烷四甲酸二酐、3,4-二羧基-1,2,3,4-四氢-1-萘琥珀酸二酐、5-(2,5-二氧代四氢呋喃基)-3-甲基-3-环己烯-1,2-二甲酸二酐、2,3,5-三羧基-2-环戊烷乙酸二酐、双环[2.2.2]辛-7-烯-2,3,5,6-四甲酸二酐、2,3,4,5-四氢呋喃四甲酸二酐、3,5,6-三羧基-2-降冰片烷乙酸二酐、1,3,3a,4,5,9b-六氢-5(四氢-2,5-二氧代-3-呋喃基)萘并[1,2-c]呋喃-1,3-二酮及下式所示的结构的酸二酐、它们的芳香族环、烃的一部分氢原子被碳原子数1~10的烷基、氟烷基、卤原子等取代而得到的化合物等,但并不限定于此。
[化学式14]
R16表示氧原子、C(CF3)2、C(CH3)2或SO2,R17及R18表示氢原子、羟基或巯基。
这些之中,优选3,3’,4,4’-联苯四甲酸二酐、2,3,3’,4’-联苯四甲酸二酐、2,2’,3,3’-联苯四甲酸二酐、3,3’,4,4’-二苯甲酮四甲酸二酐、2,2’,3,3’-二苯甲酮四甲酸二酐、2,2-双(3,4-二羧基苯基)丙烷二酐、2,2-双(2,3-二羧基苯基)丙烷二酐、1,1-双(3,4-二羧基苯基)乙烷二酐、1,1-双(2,3-二羧基苯基)乙烷二酐、双(3,4-二羧基苯基)甲烷二酐、双(2,3-二羧基苯基)甲烷二酐、双(3,4-二羧基苯基)砜二酐、双(3,4-二羧基苯基)醚二酐、2,2-双(3,4-二羧基苯基)六氟丙烷二酐、3,3’,4,4’-二苯基砜四甲酸二酐、9,9-双(3,4-二羧基苯基)芴酸二酐、9,9-双{4-(3,4-二羧基苯氧基)苯基}芴酸二酐、丁烷四甲酸二酐、1,2,3,4-环戊烷四甲酸二酐、1,2,4,5-环己烷四甲酸二酐、1,3,3a,4,5,9b-六氢-5(四氢-2,5-二氧代-3-呋喃基)萘并[1,2-c]呋喃-1,3-二酮。这些可以单独使用或者组合两种以上而使用。
通式(6)的R表示氢原子或碳原子数1~20的1价有机基团。从在碱性显影液中的溶解性、和得到的树脂组合物的溶液稳定性的观点考虑,优选R的10摩尔%~90摩尔%为氢原子。进而,更优选R含有至少一个以上的碳原子数1~16的1价烃基、且其他为氢原子。
另外,为了得到高伸长率性、高金属密合性的固化膜,相对于上述(a)树脂的上述聚酰胺与上述聚酰亚胺的结构单元合计100摩尔%而言,上述聚酰亚胺的结构单元的含量优选在2~50摩尔%的范围内。通过具有2摩尔%以上的聚酰亚胺结构,与聚酰胺结构单体的情况相比,能够提高与金属的相互作用,使制成固化膜时与金属的密合性提高,为50摩尔%以内时,能够得到由聚酰胺带来的高伸长率性。
本发明中的通式(5)~(8)表示的结构的摩尔比,可以利用根据聚合时使用的单体的摩尔比而计算的方法、或使用核磁共振装置(NMR)来检测得到的树脂、树脂组合物、固化膜中的聚酰胺结构、酰亚胺前体结构、酰亚胺结构的峰的方法加以确认。
本发明中,(a)树脂的重均分子量优选为3,000~200,000。在该范围内时,可获得在碱性显影液中的适度溶解性,因此可获得曝光部与未曝光部的高对比度,能够形成期望图案。从在碱性显影液中的溶解性的方面考虑,更优选为100,000以下,进一步优选为50,000以下。另外,从提高伸长率的方面考虑,优选为10000以上。此处,分子量可利用凝胶渗透色谱法(GPC)进行测定、并利用标准聚苯乙烯标准曲线进行换算而得到。
为了提高本发明的树脂组合物的保存稳定性,就上述聚酰胺树脂而言,可以将其主链末端用单胺、单羧酸、酸酐、单活性酯化合物等其他封端剂封端。
另外,通过用具有羟基、羧基、磺酸基、巯基、乙烯基、乙炔基、或烯丙基的封端剂将上述聚酰胺树脂的末端进行封端,由此能够容易地将上述聚酰胺树脂在碱性溶液中的溶解速度、所得固化膜的机械特性调节至优选范围内。
就封端剂的导入比例而言,为了对聚酰胺树脂的重均分子量变高、在碱性溶液中的溶解性降低进行抑制,相对于全部胺成分而言优选为0.1摩尔%以上,更优选为5摩尔%以上。另外,为了对因聚酰胺树脂的重均分子量降低而导致所得固化膜的机械特性降低进行抑制,优选为60摩尔%以下,更优选为50摩尔%以下。另外,也可以与多种封端剂反应而导入多种不同的末端基团。
关于作为封端剂的单胺,具体而言可使用M-600、M-1000、M-2005、M-2070(以上为商品名,HUNTSMAN(株)制)、苯胺、2-乙炔基苯胺、3-乙炔基苯胺、4-乙炔基苯胺、5-氨基-8-羟基喹啉、1-羟基-7-氨基萘、1-羟基-6-氨基萘、1-羟基-5-氨基萘、1-羟基-4-氨基萘、2-羟基-7-氨基萘、2-羟基-6-氨基萘、2-羟基-5-氨基萘、1-羧基-7-氨基萘、1-羧基-6-氨基萘、1-羧基-5-氨基萘、2-羧基-7-氨基萘、2-羧基-6-氨基萘、2-羧基-5-氨基萘、2-氨基苯甲酸、3-氨基苯甲酸、4-氨基苯甲酸、4-氨基水杨酸、5-氨基水杨酸、6-氨基水杨酸、2-氨基苯磺酸、3-氨基苯磺酸、4-氨基苯磺酸、3-氨基-4,6-二羟基嘧啶、2-氨基苯酚、3-氨基苯酚、4-氨基苯酚、2-氨基苯硫酚、3-氨基苯硫酚、4-氨基苯硫酚等。可以使用这些中的两种以上。
就作为封端剂的单羧酸、单活性酯化合物而言,可以使用3-羧基苯酚、4-羧基苯酚、3-羧基苯硫酚、4-羧基苯硫酚、1-羟基-7-羧基萘、1-羟基-6-羧基萘、1-羟基-5-羧基萘、1-巯基-7-羧基萘、1-巯基-6-羧基萘、1-巯基-5-羧基萘、3-羧基苯磺酸、4-羧基苯磺酸等单羧酸类及它们的羧基经酯化而得到的活性酯化合物、邻苯二甲酸酐、马来酸酐、纳迪克酸酐、环己烷二甲酸酐、3-羟基邻苯二甲酸酐等酸酐、作为二羧酸的邻苯二甲酸、马来酸、纳迪克酸、环己烷二甲酸、3-羟基邻苯二甲酸、5-降冰片烯-2,3-二甲酸、作为三羧酸的偏苯三甲酸、均苯三甲酸、二苯基醚三甲酸、对苯二甲酸、邻苯二甲酸、马来酸、环己烷二甲酸、1,5-二羧基萘、1,6-二羧基萘、1,7-二羧基萘、2,6-二羧基萘等二羧酸类的一个羧基与N-羟基苯并三唑、咪唑、N-羟基-5-降冰片烯-2,3-二甲酰亚胺反应而得到的活性酯化合物、它们的芳香族环、烃的一部分氢原子被碳原子数1~10的烷基、氟烷基、卤原子等取代而得到的化合物等。可以使用这些中的两种以上。
另外,本发明中的(a)树脂的树脂末端、树脂侧链被酰胺酸或酰胺酸酯等酰亚胺前体、酰亚胺封端而得到的结构是优选的。由于与(a)树脂的主链相比,(a)树脂末端与其他成分、基板相接触的部位更多,因此可提高密合性,提高树脂组合物的保存稳定性。因此,优选具有酰亚胺前体结构、酰亚胺前体结构,更优选作为聚酰亚胺前体结构的上述通式(6)、作为聚酰亚胺结构的通式(7)存在于(a)树脂的末端附近。由此,能够提高密合性,进一步提高(a)树脂的保存稳定性。为此,优选在进行上述聚酰胺结构的聚合后与聚酰亚胺前体结构及聚酰亚胺结构中的至少任一结构进行共聚。
(a)树脂的树脂末端、树脂侧链被酰胺酸或酰胺酸酯等酰亚胺前体、酰亚胺封端而得到的结构可以从下述化合物得到,但并不限定于此,所述化合物为:邻苯二甲酸酐、马来酸酐、纳迪克酸酐、环己烷二甲酸酐、3-羟基邻苯二甲酸酐等酸酐、作为二羧酸的邻苯二甲酸、马来酸、纳迪克酸、环己烷二甲酸、3-羟基邻苯二甲酸、5-降冰片烯-2,3-二甲酸、作为三羧酸的偏苯三甲酸、均苯三甲酸、二苯基醚三甲酸、对苯二甲酸、邻苯二甲酸、马来酸、环己烷二甲酸、1,5-二羧基萘、1,6-二羧基萘、1,7-二羧基萘、2,6-二羧基萘等二羧酸类的一个羧基与N-羟基苯并三唑、咪唑、N-羟基-5-降冰片烯-2,3-二甲酰亚胺的反应而得到的活性酯化合物、它们的芳香族环、烃的一部分氢原子被碳原子数1~10的烷基、氟烷基、卤原子等取代而得到的化合物等。
本发明中可用的封端剂可利用以下方法容易地检测。例如,将导入了封端剂的(a)树脂溶解于酸性溶液中,分解为作为结构单元的胺成分和酸酐成分,利用气相色谱(GC)、NMR对其进行检测,由此可容易地检测本发明中使用的封端剂。除此以外,也可以直接利用热解气相色谱(PGC)、红外光谱及13C-NMR光谱对导入了封端剂的树脂成分进行测定而容易地检测。
本发明中,(a)树脂可利用例如以下方法进行合成,但并不限定于此。
就聚酰胺结构而言,首先,于室温或根据情况而在升高了的温度下,将二羧酸经活性羧酸基取代而成的化合物、具有脂肪族基团的二胺、其它共聚成分溶解于有机溶剂中,接着进行加热而使它们聚合。从反应时溶液的稳定性的观点出发,就溶解的顺序而言,优选先进行溶解性高的二胺化合物的溶解。在与聚酰亚胺前体或聚酰亚胺进行共聚的情况下,然后,加入酸二酐、并根据情况而加入其它共聚成分,并加入用作封端剂的酸或酸酐而进行聚合。
要导入具有脂肪族基团的二胺时,优选使二羧酸经活性羧酸基取代而成的化合物与二胺化合物的反应于70~200℃进行。
就聚酰亚胺前体结构而言,在上述聚合方法中是来自酸酐的结构,酰胺酸酯的情况下,可通过在上述聚合后利用酯化剂使羧酸进行反应等而得到。
本发明中使用的聚酰亚胺例如可利用下述方法合成:利用制作通式(2)表示的结构的方法得到酰亚胺前体,并使其于70~200°进行聚合的方法;利用已知的酰亚胺化反应法使酰亚胺前体的酰亚胺环完全闭环的方法;另外,在中途终止酰亚胺化反应,导入部分酰亚胺结构的方法;以及,通过将使酰亚胺前体的酰亚胺环完全闭环后的已闭环的酰亚胺聚合物与上述聚酰亚胺前体混合而导入部分酰亚胺结构的方法。
本发明中使用的苯并噁唑结构例如可利用下述方法合成:得到聚酰胺,将其于150~250℃进行聚合的方法或加入酸性催化剂使其闭环的方法。作为树脂的聚合中使用的有机溶剂,例如,可举出N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基-2-吡咯烷酮、1,3-二甲基-2-咪唑啉酮、N,N’-二甲基丙烯基脲、N,N-二甲基异丁酰胺、甲氧基-N,N-二甲基丙酰胺等酰胺类、γ-丁内酯、γ-戊内酯、δ-戊内酯、γ-己内酯、ε-己内酯、α-甲基-γ-丁内酯等环状酯类、碳酸亚乙酯、碳酸亚丙酯等碳酸酯类、三乙二醇等二醇类、间甲酚、对甲酚等酚类、苯乙酮、1,3-二甲基-2-咪唑啉酮、环丁砜、二甲基亚砜、四氢呋喃、二甲基亚砜、丙二醇单甲基醚乙酸酯、乳酸乙酯等,但并不限定于此。
本发明中,就(a)树脂而言,优选在利用上述方法进行聚合后,投入到大量水或者甲醇及水的混合液等中,使其沉淀后进行过滤分离并干燥来进行分离。干燥温度优选为40~100℃、更优选为50~80℃。通过该操作,可将未反应的单体、及二聚体、三聚体等低聚物成分除去,能够使热固化后的膜特性提高。
本发明中的酰亚胺化率例如可利用以下方法容易地求出。首先,测定聚合物的红外吸收光谱,确认由聚酰亚胺引起的酰亚胺结构的吸收峰(1780cm-1附近、1377cm-1附近)的存在。接着,以将该聚合物于350°进行1小时热处理后的酰亚胺化率为100%,将其作为样品测定红外吸收光谱,通过将热处理前后的树脂的1377cm-1附近的峰强度进行比较,由此计算出热处理前树脂中的酰亚胺基的含量,求出酰亚胺化率。由于能够抑制热固化时的闭环率的变化、得到低应力化的效果,所以酰亚胺化率优选为50%以上、进一步优选为80%以上。
就本发明的树脂组合物而言,通过使上述(a)树脂为具有酚式羟基的碱溶性树脂、并含有(c)萘醌二叠氮化合物,从而能够作为正型树脂组合物使用。就使用借助光而产生酸的萘醌二叠氮化合物即光产酸剂时得到的树脂组合物而言,为通过光而可溶化的正型。通过使用萘醌二叠氮化合物,与非感光性树脂组合物(其另行通过正型光致抗蚀剂进行蚀刻)、负型感光性树脂组合物(其利用光,与树脂、交联剂反应而进行不溶化)相比,能够得到更为微细的图案,因此优选。
作为萘醌二叠氮化合物,可举出二叠氮基醌的磺酸以酯键键合于多羟基化合物而成的化合物、二叠氮基醌的磺酸以磺酰胺键键合于多氨基化合物而成的化合物、二叠氮基醌的磺酸以酯键和/或磺酰胺键键合于多羟基多氨基化合物而成的化合物等。这些多羟基化合物、多氨基化合物、多羟基多氨基化合物的并非全部官能团被醌二叠氮基取代的情况也是可以的,但优选平均而言全部官能团的40摩尔%以上被醌二叠氮基取代。通过使用这样的醌二叠氮化合物,可以得到对作为通常的紫外线的汞灯的i射线(波长365nm)、h射线(波长405nm)、g射线(波长436nm)感光的正型树脂组合物。
作为多羟基化合物,具体而言,可举出Bis-Z、BisP-EZ、TekP-4HBPA、TrisP-HAP、TrisP-PA、TrisP-SA、TrisOCR-PA、BisOCHP-Z、BisP-MZ、BisP-PZ、BisP-IPZ、BisOCP-IPZ、BisP-CP、BisRS-2P、BisRS-3P、BisP-OCHP、Methylenetris-FR-CR、BisRS-26X、DML-MBPC、DML-MBOC、DML-OCHP、DML-PCHP、DML-PC、DML-PTBP、DML-34X、DML-EP、DML-POP、Dimethylol-BisOC-P、DML-PFP、DML-PSBP、DML-MTrisPC、TriML-P、TriML-35XL、TML-BP、TML-HQ、TML-pp-BPF、TML-BPA、TMOM-BP、HML-TPPHBA、HML-TPHAP(以上为商品名,本州化学工业制)、BIR-OC、BIP-PC、BIR-PC、BIR-PTBP、BIR-PCHP、BIP-BIOC-F、4PC、BIR-BIPC-F、TEP-BIP-A、46DMOC、46DMOEP、TM-BIP-A(以上为商品名,旭有机材工业制)、2,6-二甲氧基甲基-4-叔丁基苯酚、2,6-二甲氧基甲基对甲酚、2,6-二乙酰氧基甲基对甲酚、萘酚、四羟基二苯甲酮、没食子酸甲酯、双酚A、双酚E、亚甲基双苯酚、BisP-AP(商品名,本州化学工业制)、Novolac树脂等,但并不限定于此。
作为多氨基化合物,具体而言,可举出1,4-苯二胺、1,3-苯二胺、4,4’-二氨基二苯基醚、4,4’-二氨基二苯基甲烷、4,4’-二氨基二苯基砜、4,4’-二氨基二苯基硫醚等,但并不限定于此。
另外,作为多羟基多氨基化合物,具体而言,可举出2,2-双(3-氨基-4-羟基苯基)六氟丙烷、3,3’-二羟基联苯胺等,但并不限定于此。
萘醌二叠氮化合物中,优选二叠氮基醌的磺酸以酯键键合于多羟基化合物而成的化合物。由此,可以通过i线曝光得到高的敏感度和更高的分辨率。
本发明的树脂组合物中,相对于具有酚式羟基的碱溶性树脂即(a)树脂100质量份而言,可使用的(c)萘醌二叠氮化合物的含量优选为1~50质量份,更优选为10~40质量份。通过使(c)萘醌二叠氮化合物的含量在该范围内,可获得曝光部与未曝光部的对比度,由此能够实现更高敏感度化,不会观察到在含量多时所产生的残渣,因此优选。进而,还可以根据需要添加敏化剂等。
本发明的树脂组合物含有(b)抗氧化剂。(b)抗氧化剂是用于抑制氧化而添加的抗氧化物质,本发明中,(b)抗氧化剂是指不具有交联基团的物质。就(b)抗氧化剂而言,通过使其不具有交联基团,从而不仅能够作用于交联基团可反应的部位,还能够作用于膜整体。
相对于上述(a)树脂100质量份而言,上述(b)抗氧化剂的含量优选在0.1~10质量份的范围内。添加量多于0.1质量份的情况下,可获得可靠性评价后的伸长率特性、与金属材料的密合性提高的效果。另外,少于10质量份的情况下,提高密合性,并且显影时不作为残留物残留,因此不会发生分辨率的降低、热特性的降低。另外,包含通式(1)表示的化合物的(b)抗氧化剂的添加量相对于(a)树脂而言更优选为0.2~5质量份。
通过具有(b)抗氧化剂,能够对(a)树脂的水解、吸水、酚式羟基或脂肪族基团的分解、由感光剂带来的酸的扩散进行抑制,就树脂组合物的固化膜而言,可抑制膜收缩,能够得到面内的膜厚·图案均匀性,并且可靠性评价后也能够得到高的伸长率。另外,通过含有(b)抗氧化剂,能够抑制可靠性评价后与金属布线的剥离、金属布线的金属层与氧化金属层的聚集剥离。通过高温保持试验、恒温高湿试验、热循环试验等可靠性评价,在金属布线的最外表面形成氧化金属层,所述氧化金属层是金属布线被氧、酸、水分氧化而产生的。当树脂组合物的固化膜与金属基板相接时,氧的透过被抑制,因此稍稍抑制氧化金属层的形成,但固化膜中的萘醌二叠氮化合物在可靠性评价中会分解而产生酸,由此氧化金属层的形成缓缓进行。结果,产生固化膜与金属层、氧化金属层的剥离、氧化金属层与金属层的剥离。抗氧化剂通过捕获所产生的酸,从而能够抑制氧化金属层的形成,因此可得到在可靠性评价后也具有与金属布线的高密合性的固化膜。
作为本发明中使用的(b)抗氧化剂,可举出具有苯并三唑、有机磷、受阻酚结构的抗氧化剂。其中,就具有受阻酚结构的抗氧化剂而言,显影时的溶解性、保存稳定性优异,可得到面内的膜厚·图案均匀性,并且可得到高分辨率的树脂组合物,因此优选。
作为具有苯并三唑结构的抗氧化剂,具体而言,可举出1,2,3-苯并三唑(1H-苯并三唑)、1H-苯并三唑钠盐、4-甲基-1H-苯并三唑、5-甲基-1H-苯并三唑、甲苯基三唑(4-甲基-1H-苯并三唑与5-甲基-1H-苯并三唑的混合物)、4-甲基-1H-苯并三唑钾盐、5-甲基-1H-苯并三唑钾盐、4-甲基-1H-苯并三唑胺盐、5-甲基-1H-苯并三唑胺盐、2-(3,5-二叔丁基-2-羟基苯基)-5-氯苯并三唑、2-(3,5-二叔戊基-2-羟基苯基)苯并三唑等,但并不限定于这些。
作为具有有机磷的抗氧化剂,具体而言,可举出亚磷酸三(2,4-二叔丁基苯基)酯、3,9-二(2,4-二叔丁基苯氧基)-2,4,8,10-四氧杂-3,9-二磷杂螺[5.5]十一烷、3,9-二(2,4-二异丙苯基苯氧基)-2,4,8,10-四氧杂-3,9-二磷杂螺[5.5]十一烷、亚磷酸三(对壬基苯基)酯、2,2’,2”-次氮基[三乙基-三[3,3’,5,5’-四叔丁基-1,1’-联苯基-2’-二基]亚磷酸酯]、3,9-二硬脂基氧基-2,4,8,10-四氧杂-3,9-二磷杂螺[5.5]十一烷、亚磷酸二月桂基酯、3,9-二[2,6-二叔丁基-4-甲基苯氧基]-2,4,8,10-四氧杂-3,9-二磷杂螺[5.5]十一烷、四(2,4-二叔丁基苯基)4,4’-双(联苯基)亚膦酸酯、二硬脂基季戊四醇二亚磷酸酯、二异癸基季戊四醇二亚磷酸酯、2,4,6-三-叔丁基苯基-2-丁基-2-乙基-1,3-丙二醇亚磷酸酯、三硬脂基山梨醇三亚磷酸酯、四(2,4-二叔丁基苯基)4,4’-联苯基二亚膦酸酯、(2,4,6-三叔丁基苯基)-2-丁基-2-乙基-1,3-丙二醇亚磷酸酯、亚磷酸三异癸酯,但并不限定于这些。
作为具有受阻酚结构的抗氧化剂,例如,可举出2,6-二叔丁基-4-(4,6-双(辛硫基)-1,3,5-三嗪-2-基氨基)苯酚、单叔丁基对甲酚、单叔丁基间甲酚、4-叔丁基邻苯二酚、2,5-二叔丁基对苯二酚、2,5-二叔戊基对苯二酚、没食子酸丙酯、4,4’-亚甲基双(2,6-叔丁基苯酚)、4,4’-亚异丙基双(2,6-二叔丁基苯酚)、4,4’-亚丁基双(3-甲基-6-叔丁基苯酚)、丁基羟基苯甲醚、2,6-二叔丁基对甲酚、2,6-二叔丁基苯酚、2,6-二叔丁基-4-乙基苯酚、2,4,6-三叔丁基苯酚、4-羟基甲基-2,6-二叔丁基苯酚、十八烷基-3-(4-羟基-3’,5’-二叔丁基苯基)丙酸酯、二硬脂基(4-羟基-3-甲基-5-叔丁基)苄基丙二酸酯、6-(4-羟基-3,5-二叔丁基苯胺基)2,4-双辛硫基-1,3,5-三嗪、2,6-二苯基-4-十八烷氧基苯酚、2,2’-亚甲基双(4-甲基-6-叔丁基苯酚)、2,2’-亚甲基双(4-乙基-6-叔丁基苯酚)、2,2’-亚异丁基双(4,6-二甲基苯酚)、2,2’-二羟基-3,3’-二(α-甲基环己基)-5,5’-二甲基二苯基甲烷、2,2’-亚甲基双(4-甲基-6-环己基苯酚)、三〔β-(3,5-二叔丁基-4-羟基苯基)丙酰氧基乙基〕异氰脲酸酯、1,3,5-三(2,6-二甲基-3-羟基-4-叔丁基苄基)异氰脲酸酯、三(3,5-二叔丁基-4-羟基苯酚)异氰脲酸酯、1,1,3’-三(2-甲基-4-羟基-5-叔丁基苯基)丁烷、2,6-双(2’-羟基-3’-叔丁基-5’-甲基苄基)4-甲基苯酚、N,N’-六亚甲基双(3,5-二叔丁基-4-羟基氢化肉桂酸酯)、六亚甲基二醇双〔β-(3,5-二叔丁基-4-羟基苯基)丙酸酯〕、2’,3-双[[3-[3,5-二叔丁基-4-羟基苯基]丙酰基]]丙酰肼、三乙二醇双〔β-(3-叔丁基-5-甲基-4-羟基苯基)丙酸酯、四〔亚甲基-3-(3,5-二叔丁基-4-羟基苯基)丙酸酯〕甲烷、1,3,5-三[(4-叔丁基-3-羟基-2,6-二甲苯基)甲基]-1,3,5-三嗪-2,4,6(1H,3H,5H)-三酮、1,3,5-三(3,5-二叔丁基-4-羟基苄基)-1,3,5-三嗪-2,4,6(1H,3H,5H)-三酮等,但并不限定于这些。这些可以单独使用或组合两种以上而使用。
通过在具有受阻酚结构的抗氧化剂中含有下述通式(1)表示的化合物,能够抑制固化后的膜的收缩,因此能够提高面内的膜厚·图案均匀性、以及可靠性评价后的固化后膜的伸长率特性、与金属材料的密合性。
[化学式15]
通式(1)中,R1表示氢原子或碳原子数2以上的烷基,R2表示碳原子数2以上的亚烷基。A表示包含碳原子数2以上的亚烷基、O原子、及N原子中的至少任一者的1~4价有机基团。k表示1~4的整数。通式(1)表示的化合物中,R2具有柔软的亚烷基,因此受阻酚结构能够柔性地运动,因此容易抑制固化膜整体的氧化劣化。另外,通过对金属材料赋予防锈作用,能够抑制金属材料的金属氧化。另外,R2具有柔软的亚烷基时,还能够提高涂布时的面内膜厚均匀性,从这一观点考虑也是优选的。
另外,通式(1)中,k为2~4的整数时,作用于树脂组合物和金属材料这两者,因此更优选。作为A,可举出烷基、环烷基、烷氧基、烷基醚基、烷基甲硅烷基、烷氧基甲硅烷基、芳基、芳基醚基、羧基、羰基、烯丙基、乙烯基、杂环基、-O-、-NH-、-NHNH-、它们的组合等,也可以进一步具有取代基。其中,从在显影液中的溶解性、金属密合性的观点考虑,优选具有烷基醚基、-NH-,从与(a)树脂的相互作用及由形成金属络合物带来的金属密合性的观点考虑,更优选具有-NH-。
关于通式(1)表示的化合物,可举出以下化合物作为例子,但并不限于下述结构。
[化学式16]
[化学式17]
[化学式18]
[化学式19]
本发明的树脂组合物为含有(d)交联剂的树脂组合物,其中,上述(d)交联剂在一分子中具有酚式羟基、并且在上述酚式羟基的两个邻位具有分子量为40以上的取代基。所谓交联剂,是指具有交联性基团的材料,所述交联性基团为能够通过自由基反应、加成反应、缩合反应等进行交联的官能团。
通过含有该交联剂,从而实现由膜密度提高(抑制氧透过、抑制金属扩散)带来的抑制氧化劣化的效果。
(d)交联剂中,分子量为40以上的大体积结构与酚式羟基相邻,因此可得到固化时交联密度高的致密膜。因此,抑制氧透过固化膜并抑制金属向固化膜的扩散,能够有效地抑制树脂的氧化劣化、金属腐蚀,结果,使得可靠性评价后、固化后的膜的伸长率特性、与金属材料的密合性提高。
通过含有该交联剂,能够实现由防止氧化带来的对氧化劣化的抑制。
另外,通过使分子量为40以上的大体积结构与酚式羟基相邻,从而能够发挥与具有受阻酚结构的抗氧化剂同样的效果。因此,在对于(b)抗氧化剂单体而言难以邻接的致密的交联部位,也可获得抑制氧化的效果。因此,除了作为交联剂本身的功能外,还能够抑制交联剂已交联的部位的氧化劣化、已交联的部位周边的(a)树脂的脂肪族基团、酚式羟基的氧化劣化,并且通过对金属材料赋予防锈作用从而抑制金属氧化。但是,由于是交联剂,(d)交联剂容易偏在于膜中交联基团可反应的部位,因此虽然在交联部周边可获得高的抑制氧化劣化的效果,但为了在膜整体中获得抗氧化的效果,必须与(b)抗氧化剂组合。
如上所述,通过由(b)抗氧化剂带来的对固化膜整体的作用、由(d)交联剂带来基于膜密度提高而获得的氧透过性抑制、由(d)交联剂的抗氧化结构带来的对交联部位周边的作用,从而能够有效地抑制氧化劣化、金属腐蚀。另外,(d)交联剂在热固化时与树脂的未闭环部位交联,由此能够抑制由树脂的剧烈闭环导致的膜厚·图案收缩,在固化膜中,可获得良好的面内膜厚·图案均匀性。
作为分子量为40以上的取代基,优选异丙基、叔丁基、烷氧基甲基。其中,就烷氧基甲基而言,除了作为交联基团发挥作用,另一方面,于低温进行固化时,在固化后也残留,由此防止可靠性评价时的氧化,因此优选。
关于(d)交联剂,可举出以下化合物作为例子,但并不限于下述结构。
[化学式20]
[化学式21]
进而,上述(d)交联剂优选为在一分子中具有3个以上的酚式羟基的交联剂。通过具有3个以上的有抗氧化效果的酚式羟基,从而能够有效地作用于(a)树脂、金属这两者,能够赋予可靠性评价后的特性。作为这样的优选例,可举出以下化合物,但并不限于下述结构。
[化学式22]
(式中c、d、及e各自表示1以上的整数,优选3≤c≤20、1≤d≤30、1≤c≤30。)
另外,相对于上述(a)树脂100质量份而言上述(d)交联剂的含量在15~70质量份的范围内是优选的。为15质量份以上的情况下,可获得固化膜的高密度化和抗氧化效果,能够大幅抑制可靠性评价后的伸长率降低。为70质量份以下时,可获得提高固化膜的伸长率的效果,减少膜的裂纹,另外,也能够使得与金属布线的密合性提高。
本发明的树脂组合物可以含有除(d)以外的其他热交联剂。具体而言,优选具有至少两个烷氧基甲基或羟甲基的化合物。通过具有至少两个上述基团,能够与树脂及同种分子发生缩合反应而形成交联结构体。通过与光产酸剂并用,能够为了提高敏感度、固化膜的机械特性而提供更宽范围的设计。
作为其他热交联剂的优选例,例如可举出MX-290、NIKALAC MX-280、NIKALAC MX-270、NIKALAC MX-279、NIKALAC MW-100LM、NIKALAC MX-750LM(以上为商品名,(株)三和化学制)。可以含有它们中的两种以上。
本发明的树脂组合物优选含有(e)通式(3)表示的化合物。通过含有(e)通式(3)表示的化合物,从而显著提高加热固化后的膜与金属材料、尤其是与铜的密合性。
[化学式23]
这归因于通式(3)表示的化合物的S原子、N原子与金属表面发生相互作用,进而形成了容易与金属表面发生相互作用的立体结构。基于这些效果,能够对树脂组合物赋予感光性,即使在具有添加剂的组成中也能够得到与金属材料的粘接性优异的树脂固化膜。通式(3)中,R7~R9表示N原子、O原子或S原子中的任一者,R7~R9中的至少一个表示S原子。l表示0或1,m、n表示0~2的整数。R10~R12各自独立地表示氢原子或碳原子数1~20的有机基团。作为R10~R12,可举出氢原子、烷基、环烷基、烷氧基、烷基醚基、烷基甲硅烷基、烷氧基甲硅烷基、芳基、芳基醚基、羧基、羰基、烯丙基、乙烯基、杂环基、它们的组合等,也可以进一步具有取代基。
另外,相对于(a)树脂而言,通式(3)表示的化合物的添加量优选为0.1~15质量份,更优选为0.5~15质量份。添加量少于0.1质量份时,难以获得与金属材料的密合性提高的效果,另外,多于15质量份时,因与感光剂的相互作用而有可能导致树脂组合物的敏感度降低。
优选地,本发明中使用的通式(3)表示的化合物中,R7~R9表示N原子、O原子或S原子中的任一者,R7~R9中的至少一个为S原子。一般而言,在添加含有N原子的化合物的情况下,存在由于感光剂与含N原子的化合物的相互作用而损害敏感度的可能性,但通过含有S原子,可适当地保持相互作用效果,能够在不使敏感度降低的情况下得到密合性提高的效果。另外,从与金属以外的基板的密合性的观点考虑,更优选具有三烷氧基甲基。
关于通式(3)表示的化合物,可举出以下的化合物作为例子,但并不限于下述结构。
[化学式24]
[化学式25]
[化学式26]
[化学式27]
[化学式28]
本发明的树脂组合物通过含有(f)具有下述通式(4)表示的结构单元的热交联剂,能够进一步实现伸长率提高和低应力化。
[化学式29]
通式(4)中,R13及R14各自独立地表示氢原子或甲基。R15为具有碳原子数2以上的亚烷基的2价有机基团,直链状、支链状、及环状均可。R15可举出烷基、环烷基、烷氧基、烷基醚基、烷基甲硅烷基、烷氧基甲硅烷基、芳基、芳基醚基、羧基、羰基、烯丙基、乙烯基、杂环基、它们的组合等,也可以进一步具有取代基。
由于热交联剂本身具有柔软的亚烷基和刚性的芳香族基团,因此能够在具有耐热性的同时实现伸长率提高和低应力化。作为交联基团,可举出丙烯酸系基团、羟甲基、烷氧基甲基、环氧基,但并不限定于此。其中,从能够与(a)树脂的酚式羟基反应、提高固化膜的耐热性的观点、和能够不脱水地进行反应的观点考虑、以及由于能够实现由低收缩率化带来的面内均匀性提高,环氧基是优选的。
关于通式(4)表示的化合物,例如,可举出以下的化合物作为例子,但并不限于下述结构。
[化学式30]
(式中n为1~5的整数,m为1~20的整数。)
上述结构中,从同时实现耐热性和伸长率提高的观点考虑,优选地,n为1~2、m为3~7。
另外,相对于(a)树脂而言,通式(4)表示的化合物的添加量优选为2~35质量份,更优选为5~25质量份。添加量少于2质量份时,难以获得伸长率提高和低应力化的效果,另外,多于35质量份时,可能导致树脂组合物的敏感度降低。
另外,通过使上述通式(1)表示的化合物的含量相对于具有通式(4)表示的结构单元的热交联剂100质量份而言在10质量份~50质量份的范围内,能够显著地提高可靠性后评价后的固化膜的伸长率特性。其原因在于,在该范围内时,在固化膜中促进具有通式(4)表示的结构单元的热交联剂的交联,从而抑制在可靠性评价后亚烷基的氧化劣化。另外,可根据需要在不使固化后的收缩残膜率减小的范围内含有具有酚式羟基的低分子化合物。由此,能够缩短显影时间。
作为这些化合物,例如可举出Bis-Z、BisP-EZ、TekP-4HBPA、TrisP-HAP、TrisP-PA、BisOCHP-Z、BisP-MZ、BisP-PZ、BisP-IPZ、BisOCP-IPZ、BisP-CP、BisRS-2P、BisRS-3P、BisP-OCHP、Methylenetris-FR-CR、BisRS-26X(以上为商品名,本州化学工业(株)制)、BIP-PC、BIR-PC、BIR-PTBP、BIR-BIPC-F(以上为商品名,旭有机材工业(株)制)等。可以含有它们中的两种以上。
关于具有酚式羟基的低分子化合物的含量,优选相对于(a)树脂100质量份而言含有1~40质量份。
本发明的树脂组合物优选含有溶剂。作为溶剂,可举出N-甲基-2-吡咯烷酮、γ-丁内酯、γ-戊内酯、δ-戊内酯、N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、二甲基亚砜、1,3-二甲基-2-咪唑啉酮、N,N’-二甲基丙烯基脲、N,N-二甲基异丁酰胺、甲氧基-N,N-二甲基丙酰胺等极性的非质子性溶剂、四氢呋喃、二氧杂环己烷、丙二醇单甲基醚、丙二醇单乙基醚等醚类、丙酮、甲基乙基酮、二异丁基酮等酮类、乙酸乙酯、乙酸丁酯、乙酸异丁酯、乙酸丙酯、丙二醇单甲基醚乙酸酯、3-甲基-3-甲氧基丁基乙酸酯等酯类、乳酸乙酯、乳酸甲酯、二丙酮醇、3-甲基-3-甲氧基丁醇等醇类、甲苯、二甲苯等芳香族烃类等。可以含有它们中的两种以上。
关于溶剂的含量,为了使组合物溶解,优选相对于(a)树脂100质量份而言含有100质量份以上,为了形成膜厚为1μm以上的涂膜,优选含有1,500质量份以下。
出于提高与基板的润湿性的目的,本发明的树脂组合物也可以含有表面活性剂、乳酸乙酯、丙二醇单甲基醚乙酸酯等酯类、乙醇等醇类、环己酮、甲基异丁基酮等酮类、四氢呋喃、二氧杂环己烷等醚类。
另外,为了提高与基板的粘接性,也可以在不损害保存稳定性的范围内,在本发明的树脂组合物中作为硅氧烷成分而含有三甲氧基氨基丙基硅烷、三甲氧基环氧基硅烷、三甲氧基乙烯基硅烷、三甲氧基巯基丙基硅烷等硅烷偶联剂。
关于硅烷偶联剂的优选含量,相对于(a)树脂100质量份而言为0.01~5质量份。
本发明的树脂组合物可以具有其他树脂。具体而言,可举出聚酰亚胺前体、聚酰亚胺树脂、聚苯并噁唑、聚苯并噁唑前体、聚酰胺树脂、硅氧烷树脂、共聚有丙烯酸的丙烯酸聚合物、Novolac树脂、Resol树脂、聚羟基苯乙烯树脂、以及在这些中导入了羟甲基、烷氧基甲基、环氧基等交联基团的改性物、它们的共聚聚合物等。这样的树脂溶解在四甲基氢氧化铵、胆碱、三乙胺、二甲基氨基吡啶、单乙醇胺、二乙基氨基乙醇、氢氧化钠、氢氧化钾、碳酸钠等碱的溶液中。通过含有这些碱溶性树脂,可以在保持固化膜的密合性、优异的敏感度的同时赋予各碱溶性树脂的特性。
其中,除了提高敏感度外,还因固化前后的收缩变化率低而能够实现低应力化,因此优选Novolac树脂、Resol树脂、以及在它们中导入了羟甲基、烷氧基甲基、环氧基等交联基团的改性物等酚醛树脂。
作为这些树脂的优选含量,相对于本发明的(a)树脂100质量份而言,为5~200质量份,更优选为15~150质量份。
进而,在本发明的树脂组合物中,也可以在不使固化后的收缩率变大的范围内含有溶解调节剂。作为溶解调节剂,只要使多羟基化合物、磺酰胺化合物、脲化合物等通常在正型抗蚀剂中用作溶解调节剂的化合物即可,可优选使用任意化合物。特别地,优选使用作为合成醌二叠氮化合物时的原料的多羟基化合物。
本发明的树脂组合物的粘度优选为2~5,000mPa·s。粘度可使用E型旋转粘度计进行测定。通过调节固态成分浓度以使得粘度成为2mPa·s以上,容易得到期望的膜厚。另一方面,粘度为5,000mPa·s以下时,容易得到均匀性高的涂布膜。具有这样的粘度的树脂组合物例如可通过使固态成分浓度为5~60质量%而容易地得到。
接着,对作为使用了本发明的树脂组合物的固化膜的固化膜浮凸图案的形成方法进行说明。
首先,将本发明的树脂组合物涂布于基板上。作为基板,可举出硅晶片、陶瓷类、砷化镓、有机类电路基板、无机类电路基板、硅晶片与环氧树脂等密封树脂的复合基板、及在这些基板上配置有电路的构成材料的基板等,但并不限定于这些。作为有机类电路基板的例子,可举出玻璃布/环氧覆铜层叠板等玻璃基板覆铜层叠板、玻璃无纺布/环氧覆铜层叠板等复合覆铜层叠板、临时贴合载体基板、聚醚酰亚胺树脂基板、聚醚酮树脂基板、聚砜类树脂基板等耐热/热塑性基板、聚酯覆铜膜基板、聚酰亚胺覆铜膜基板等柔性基板。另外,无机类电路基板的例子可举出玻璃基板、氧化铝基板、氮化铝基板、碳化硅基板等陶瓷基板、铝基基板、铁基基板等金属类基板。电路的构成材料的例子可举出含有银、金、铜等金属的导体、含有无机类氧化物等的电阻、含有玻璃类材料和/或树脂等的低电介质、含有树脂、高介电常数无机粒子等的高电介质、含有玻璃类材料等的绝缘体等。
关于金属布线,由于会因空气氧化而使表面状态变化,因此优选预先进行氧等离子体处理、用过氧化氢水溶液等进行氧化处理。
作为涂布方法,可举出使用旋涂机的旋涂、喷涂、辊涂、丝网印刷、刮涂法、模涂法、压延涂布法、弯月面涂布法、棒涂法、辊涂法、逗号辊涂法、凹版辊涂法、丝网涂布法、缝模涂布法等方法。另外,涂布膜厚根据涂布方法、组合物的固态成分浓度、粘度等的不同而不同,通常以使得干燥后的膜厚成为0.1~150μm的方式进行涂布。制成感光性未固化片材的情况下,之后使其干燥而剥离。
为了提高硅晶片等基板与树脂组合物的粘接性,还可以利用前述的硅烷偶联剂对基板进行前处理。例如,将硅烷偶联剂以0.5~20质量%溶解于异丙醇、乙醇、甲醇、水、四氢呋喃、丙二醇单甲基醚乙酸酯、丙二醇单甲基醚、乳酸乙酯、己二酸二乙酯等溶剂中制成溶液,将所述溶液利用旋涂、浸渍、喷涂、蒸气处理等进行表面处理。根据情况,之后进行热处理直到50℃~300℃为止,使基板与硅烷偶联剂的反应进行。
接着,将树脂组合物或感光性未固化片材涂布或层压在基板上,对得到的基板进行干燥,得到树脂组合物被膜。干燥优选使用烘箱、加热板、红外线等、在50℃~150℃的范围内进行1分钟~数小时。
接着,通过具有期望图案的掩模对该树脂组合物被膜上照射光化射线,进行曝光。作为曝光中使用的光化射线,有紫外线、可见光线、电子线、X射线等,在本发明中,优选使用汞灯的i线(365nm)、h线(405nm)、g线(436nm)。
为了形成图案,在曝光后使用显影液,对于正型的情况而言将曝光部除去,对于负型的情况而言将未曝光部除去。作为显影液,优选为四甲基氢氧化铵、二乙醇胺、二乙基氨基乙醇、氢氧化钠、氢氧化钾、碳酸钠、碳酸钾、三乙胺、二乙胺、甲胺、二甲胺、乙酸二甲基氨基乙酯、二甲基氨基乙醇、甲基丙烯酸二甲基氨基乙酯、环己胺、乙二胺、六亚甲基二胺等显示碱性的化合物的溶液。另外,根据情况,也可以向这些碱性溶液中添加下述中的单独一种或组合添加多种:N-甲基-2-吡咯烷酮、N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、二甲基亚砜、γ-丁内酯、二甲基丙烯酰胺等极性溶剂、甲醇、乙醇、异丙醇等醇类、乳酸乙酯、丙二醇单甲基醚乙酸酯等酯类、环戊酮、环己酮、异丁酮、甲基异丁基酮等酮类等。显影可通过下述方法进行:将上述显影液喷雾于被膜面;在显影液中浸渍;或者在浸渍的同时施加超声波;在使基板旋转的同时喷雾显影液;等等。优选在显影后利用水进行漂洗处理。这里,也可以将乙醇、异丙醇等醇类、乳酸乙酯、丙二醇单甲基醚乙酸酯等酯类等加入到水中而进行漂洗处理。
显影后,施加150℃~500℃的温度进行热交联反应。通过交联,可提高耐热性及耐药品性。该加热处理的方法可选择下述方法:选择温度,阶段性地进行升温的方法;选择某温度范围,一边连续地升温一边实施5分钟~5小时的方法。作为前者的一例,可举出在130℃、200℃各进行30分钟热处理的方法。作为后者的一例,可举出经2小时从室温直线性地升温至400℃等方法。作为本发明中的固化条件,优选为150℃以上且350℃以下,由于本发明提供特别是在低温固化性方面优异的固化膜,因此更优选为160℃以上且250℃以下。
作为本发明中的加热处理、即固化条件,优选为170℃以上且400℃以下。为了获得低应力的效果,更优选为170℃以上且250℃以下。
将本发明的树脂组合物固化而成的固化膜的断裂点伸长率优选为30%以上,更优选为50%以上。与多种材料接触的层间绝缘膜容易受到由热膨胀系数差带来的负荷,因此需要更高伸长率的材料。将本发明的树脂组合物固化而成的固化膜具有高伸长率性,因此在可靠性评价时也不易产生固化膜的裂纹、与金属布线的剥离。作为可靠性评价,可举出冲击试验、高温保持试验、恒温高湿试验、热循环试验。将本发明的树脂组合物固化而成的固化膜可用于半导体器件、多层布线板等电子部件。具体而言,可合适地用于半导体的钝化膜、半导体元件的表面保护膜、层间绝缘膜、高密度封装用多层布线的层间绝缘膜、有机电致发光元件的绝缘层等用途,但并不限定于此,可采用各种结构。
接下来,使用附图,对向使用了本发明的树脂组合物且具有凸块的半导体器件的应用例进行说明(应用例1)。图1为本发明的具有凸块的半导体器件的焊盘部分的放大截面图。如图1所示,在硅晶片1上,在输入输出用的铝(以下,记为A1)焊盘2上形成有钝化膜3,在该钝化膜3中形成有通孔。进而在其上,以由本发明的树脂组合物得到的图案的形式形成有绝缘膜4,进而以与Al焊盘2连接的方式形成有金属(Cr、Ti等)膜5,通过电镀等形成有金属布线(Al、Cu等)6。在焊料凸块10的周边对金属膜5进行蚀刻,从而将各焊盘间绝缘。在被绝缘的焊盘上形成势垒金属8和焊料凸块10。绝缘膜7的树脂组合物可以在划片槽9中进行厚膜加工。在树脂组合物中导入有柔软成分的情况下,晶片的翘曲小,因此能够高精度地进行曝光、晶片的搬运。另外,本发明的树脂的高伸长率性也优异,因此通过树脂本身的变形,从而在封装时也能够缓和来自密封树脂的应力,因此防止凸块、布线、低介电常数(low-k)层的损伤,能够提供高可靠性的半导体器件。
接着,关于半导体器件的详细制作方法,在图2中记述。如图2的2a所示,在硅晶片1上形成有输入输出用的Al焊盘2、以及钝化膜3,并且以由本发明的树脂组合物得到的图案的形式形成有绝缘膜4。接着,如图2的2b所示,以与Al焊盘2连接的方式形成有金属(Cr、Ti等)膜5,如图2的2c所示,利用镀覆法将金属布线6成膜。接着,如图2的2d’所示,涂布本发明的树脂组合物,经由光刻工序,作为如图2的2d所示那样的图案而形成绝缘膜7。在绝缘膜7上可进一步形成布线(所谓的再布线)。在形成2层以上的多层布线结构的情况下,通过重复进行上述工序,从而能够形成2层以上的再布线被由本发明的树脂组合物得到的层间绝缘膜分隔开的多层布线结构。此时,虽然所形成的绝缘膜与各种药液多次接触,但因为由本发明的树脂组合物得到的绝缘膜的密合性优异,因此能够形成良好的多层布线结构。多层布线结构的层数没有上限,大多使用10层以下。此时,绝缘膜7的树脂组合物在划片槽9中进行厚膜加工。在形成3层以上的多层布线结构的情况下,可以重复进行上述工序而形成各层。
接着,如图2的2e及2f所示,形成势垒金属8、焊料凸块10。然后,沿着最后的划片槽9进行切割而切分成各芯片。
接着,使用附图,对向使用了本发明的树脂组合物且具有凸块的半导体器件的应用例2进行说明。图3为具有本发明的绝缘膜的半导体器件的焊盘部分的放大截面图,是被称为扇出型晶圆级封装(扇出型WLP)的结构。与上述应用例1同样地,形成有Al焊盘2、钝化膜3的硅晶片1被切割而切分成各芯片,然后用树脂11进行密封。在该密封树脂11和芯片上,以由本发明的树脂组合物得到的图案的形式形成有绝缘膜4,进而形成金属(Cr、Ti等)膜5、金属布线6。然后,在形成于芯片外的密封树脂上的绝缘膜7的开口部中,形成势垒金属8和焊料凸块10。扇出型WLP为下述半导体封装:通过使用环氧树脂等密封树脂在半导体芯片的周边设置扩展部分,从半导体芯片上的电极直至该扩展部分实施再布线,并在扩展部分也搭载焊球,从而确保了必要的端子数的半导体封装。在扇出型WLP中,以跨越半导体芯片的主面与密封树脂的主面所形成的边界线的方式设置有布线。即,在包含施以了金属布线的半导体芯片及密封树脂这两种以上的材料的基材上形成层间绝缘膜,在该层间绝缘膜上形成布线。
另外,扇出型WLP中存在利用被称为RDL-First的工序制作的类型的封装,即,在配置有临时粘贴材料的支承基板上作为再布线间的层间绝缘膜进行配置,并在层间绝缘膜上配置硅芯片和密封树脂,然后将配置有临时粘贴材料的支承基板与再布线剥离。在该工序中,出于由大量生产带来的成本方面优点的目的而使用大面积面板,因此由层间绝缘膜的膜收缩导致的翘曲、膜厚·图案的面内均匀性将成为课题。
使用图5,对RDL-First中的半导体器件的制作方法进行说明。在图5的3a中,利用溅射法在支承基板20上形成Ti等势垒金属,进而利用溅射法在其上形成Cu晶种(晶种层),然后利用镀覆法形成电极焊盘21。在接下来的3b工序中,涂布本发明的感光性树脂组合物,经由光刻工序,形成绝缘膜22(其形成图案)。接着,在3c工序中,再次利用溅射法形成晶种层,利用镀覆法形成金属布线23(再布线层)。以下,为了使半导体芯片的导通部间距与金属布线的间距对应,重复进行3b及3c的工序,形成如3d所示那样的多层布线结构。接着,在3e的工序中,再次涂布本发明的感光性树脂组合物,经由光刻工序而形成绝缘膜(其形成图案),然后利用镀覆法形成Cu柱24。此处,Cu柱的间距与半导体芯片的导通部间距相同。即,一边将金属布线间距缩窄,一边对再布线层进行多层化,因此如图3的3e所示,就层间绝缘膜的膜厚而言,层间绝缘膜1>层间绝缘膜2>层间绝缘膜3>层间绝缘膜4>。接着,在3f工序中,介由焊料凸块25与半导体芯片26连接,能够得到具有多层布线结构的使用RDL-First的半导体器件。除此以外,对于将半导体芯片埋入到形成于玻璃环氧树脂基板上的凹部这种类型的半导体封装而言,以跨越半导体芯片的主面与印刷基板的主面的边界线的方式设置布线。在这种方式中,也在由两种以上的材料构成的基材上形成层间绝缘膜,在该层间绝缘膜上形成布线。对于将本发明的树脂组合物固化而成的固化膜而言,具有高伸长率、及与已施以金属布线的半导体芯片的高密合力,并且与环氧树脂等密封树脂也具有高的密合力,因此适合用作设置于由两种以上的材料构成的基材上的层间绝缘膜。
另外,在扇出型WLP中,再布线的微细化不断发展。就本发明的树脂组合物的固化膜而言,与金属布线的宽度及相邻布线彼此的间隔为5μm以下的布线也具有高的金属密合性,因此也可合适地用于微细的再布线中。
在该结构中,就层间绝缘膜的厚度而言,随着接近半导体芯片而变薄,另外,就再布线层而言,随着接近半导体芯片,金属布线的宽度及相邻布线彼此的间隔变窄,由此与芯片的高集成化相对应。因此,高分辨率化、以及在具有台阶的再布线上的面内均匀性成为重要的课题。
接着,使用附图,对向使用了本发明的树脂组合物的感应器装置的线圈部件的应用例3进行说明。图4为具有本发明的绝缘膜的线圈部件的截面图。如图4所示,在基板12上形成有绝缘膜13,在其上以图案形式形成有绝缘膜14。作为基板12,使用铁素体等。本发明的树脂组合物可用于绝缘膜13和绝缘膜14中的任意。在该图案的开口部中形成有金属(Cr、Ti等)膜15,在其上镀覆形成有金属布线(Ag、Cu等)16。金属布线16(Ag、Cu等)形成为螺旋状。将13~16的工序重复多次,使其层叠,由此可具有线圈的功能。最后,金属布线16(Ag、Cu等)通过金属布线17(Ag、Cu等)与电极18连接,通过密封树脂19而被密封。
本发明的树脂组合物也适合用于有机EL显示装置。该有机EL显示装置在基板上具有驱动电路、平坦化层、第1电极、绝缘层、发光层及第2电极,其中,平坦化层及/或绝缘层由本发明的固化膜形成。近年来,有机EL显示装置寻求在100℃左右的高温保持或热循环试验这样的可靠性评价中的耐久性。本发明的固化膜在这些可靠性评价后也具有高伸长率且具有与金属布线、金属电极的高密合性,因此可获得稳定的驱动及发光特性。举出有源矩阵型显示装置为例时,在玻璃、各种塑料等基板上具有TFT、和位于该TFT的侧面且与TFT连接的布线,在其上以覆盖凹凸的方式具有平坦化层,进而在平坦化层上设置显示元件。显示元件与布线介由形成于平坦化层中的接触孔连接。
图6中示出TFT基板的一例的截面图。在基板32上,呈行列状地设置有底栅型或顶栅型的TFT(薄膜晶体管)27,以覆盖该TFT27的状态形成有绝缘层29。另外,在该绝缘层29上设置有与TFT27连接的布线28。进而,在绝缘层29上,以掩埋布线28的状态设置有平坦化层30。在平坦化层30中设置有达到布线28的接触孔33。然后,介由该接触孔33,以与布线28连接的状态在平坦化层30上形成有ITO(透明电极)31。此处,ITO31成为显示元件(例如有机EL元件)的电极。然后,以覆盖ITO31的周缘的方式形成绝缘层34。有机EL元件可以为从与基板32相反一侧释放所发出的光的顶部发光型,也可以为从基板32侧提取光的底部发光型。如此地,可得到各有机EL元件与用于将其驱动的TFT27连接而成的有源矩阵型有机EL显示装置。
如前文所述,上述绝缘层29、平坦化层30及/或绝缘层34可以通过下述工序形成:形成由本发明的树脂组合物或树脂片材形成成的感光性树脂膜的工序;对上述感光性树脂膜进行曝光的工序;对经曝光的感光性树脂膜进行显影的工序;及对经显影的感光性树脂膜进行加热处理的工序。利用包括这些工序的制造方法,可得到有机EL显示装置。
实施例
以下,举出实施例对本发明进行说明,但本发明并不受这些例子限定。首先,对各实施例及比较例中的评价方法进行说明。在评价中,使用了预先利用1μm的聚四氟乙烯制过滤器(住友电气工业(株)制)进行过滤的各实施例、比较例中制作的树脂组合物(以下称为清漆)。
(1)分子量测定、酰亚胺化率测定
(a)树脂的重均分子量(Mw)使用GPC(凝胶渗透色谱法)装置Waters 2690-996(Japan Waters(株)制)来确认。使展开溶剂为N-甲基-2-吡咯烷酮(以下称为NMP)来进行测定,计算以聚苯乙烯换算的重均分子量(Mw)及分散度(PDI=Mw/Mn)。
另外,关于树脂的酰亚胺化率,在硅晶片上旋涂将树脂溶解于γ-丁内酯而得到的溶液,于120℃干燥3分钟,制成膜厚为5μm的涂布膜,测定红外吸收光谱,确认酰亚胺结构的吸收峰(1780cm-1附近、1377cm-1附近)的存在。接着,以将该涂布膜于350℃进行热处理1小时后的酰亚胺化率作为100%,将其作为样品测定红外吸收光谱,并将热处理前后的树脂在1377cm-1附近的峰强度进行比较,由此计算出热处理前树脂中的酰亚胺基的含量,求出酰亚胺化率。红外吸收光谱的测定使用“FT-720”(商品名,株式会社堀场制作所制)作为测定装置。
(2)-1分辨率的评价
使用涂布显影装置ACT-8(Tokyo Electron Ltd.制),利用旋涂法,以膜厚成为10.5μm~12μm的方式将清漆涂布于8英寸的硅晶片上,于120℃进行3分钟预烘烤。在i线步进曝光机DSW-8000(GCA公司制)上设置切有圆形的通孔图案(via pattern)的光罩(reticle),以1500mJ/cm2的曝光量进行曝光。曝光后,使用ACT-8的显影装置,使用2.38质量%的四甲基铵水溶液(以下记为TMAH,多摩化学工业(株)制),利用旋覆浸没(puddle)法,将显影液的排出时间设为10秒、旋覆浸没时间设为40秒的显影反复进行2次,然后用纯水进行漂洗,然后甩干,得到膜厚为10μm的图案。使用平板显示器显微镜MX61(Olympus(株)制),以20倍的倍率对图案进行观察,将分辨通孔图案的最小尺寸作为分辨率。
另外,关于未添加(c)萘醌二叠氮化合物、聚合引发剂、光聚合性化合物的感光剂的非感光树脂组合物,使用涂布显影装置ACT-8(Tokyo Electron Ltd.制),利用旋涂法,以膜厚成为10.5μm~12μm的方式将清漆涂布于8英寸的硅晶片上,进而于120℃涂布正型抗蚀剂OFPR-800(东京应化(株)制)并进行3分钟预烘烤。在i线步进曝光机DSW-8000(GCA公司制)上设置切有圆形的通孔图案的光罩,以1500mJ/cm2的曝光量进行曝光。曝光后,使用ACT-8的显影装置,使用2.38质量%的四甲基铵水溶液(以下记为TMAH,多摩化学工业(株)制),利用旋覆浸没法,将显影液的排出时间设为10秒、旋覆浸没时间设为40秒的显影重复2次,然后用纯水进行漂洗,然后甩干,未曝光部的抗蚀剂用丙酮剥离,然后得到膜厚为10μm的正型图案。使用平板显示器显微镜MX61(Olympus(株)制),以20倍的倍率对图案进行观察,将分辨通孔图案的最小尺寸作为分辨率。
(2)-2面内均匀性(膜厚)的评价
以使得于120℃进行3分钟预烘烤后的膜厚成为11μm的方式,使用涂布显影装置ACT-8,利用旋涂法,将清漆涂布于8英寸的硅晶片上并进行预烘烤,然后使用惰性气体烘箱CLH-21CD-S(Koyo Thermo System(株)制),在氧浓度为20ppm以下的条件下,以3.5℃/分钟升温至190℃,于190℃进行1小时加热处理。温度达到50℃以下时取出晶片,缓慢冷却后,针对8英寸晶片,从中央起以左右2cm的间隔,使用平板显示器显微镜MX61(Olympus(株)制),测定9点的膜厚,将膜厚的最小值与最大值之差作为膜厚的面内均匀性。将膜厚的面内均匀性的值小于0.15μm的情况评价为极为良好(A),将为0.15μm以上且小于0.4μm的情况评价为良好(B),将为0.4μm以上且小于0.8μm的情况评价为尚可(C),将为0.8μm以上的情况评价为不好(D)。
(2)-3面内均匀性(图案)的评价
针对与(2)-2同样的图案,从8英寸晶片的中央起以左右2cm的间隔制作9射域(shot),使用惰性气体烘箱CLH-21CD-S(Koyo Thermo System(株)制),在氧浓度为20ppm以下的条件下,以3.5℃/分钟升温至190℃,于190℃进行1小时加热处理。在温度达到50℃以下时取出晶片,缓缓冷却后,在9射域中,使用扫描激光显微镜1LM21(LASERTEC(株)制),测定各分辨率的图案尺寸,将尺寸的最小值与最大值之差作为图案的面内均匀性。将图案的面内均匀性的值小于0.8μm的情况评价为极为良好(A),将为0.8μm以上且小于1.2μm的情况评价为良好(B),将为1.2μm以上且小于1.5μm的情况评价为尚可(C),将为1.5μm以上的情况评价为不好(D)。
(3)-1伸长率性评价
以使得于120℃进行3分钟预烘烤后的膜厚成为11μm的方式,使用涂布显影装置ACT-8,利用旋涂法,将清漆涂布于8英寸的硅晶片上并进行预烘烤,然后使用惰性气体烘箱CLH-21CD-S(Koyo Thermo System(株)制),在氧浓度为20ppm以下的条件下,以3.5℃/分钟升温至190℃,于190℃进行1小时加热处理。在温度达到50℃以下时取出晶片,缓慢冷却后,在45质量%的氢氟酸中浸渍5分钟,由此将树脂组合物的膜从晶片剥离。将该膜切成宽度为1cm、长度为9cm的长条状,使用Tensilon RTM-100((株)Orientec制),在室温23.0℃、湿度45.0%RH的条件下以50mm/分钟的拉伸速度进行拉伸,进行断裂点伸长率的测定。针对每一被检物,对10个长条进行测定,并由结果求出较高的5个点的平均值。将断裂点伸长率的值为80%以上的情况评价为极为良好(A),将为50%以上且小于80%的情况评价为良好(B),将为25%以上且小于50%的情况评价为尚可(C),将小于25%的情况评价为不好(D)。
(3)-2热循环试验(TC)后的伸长率性评价
以于120℃进行3分钟预烘烤后的膜厚成为11μm的方式,使用涂布显影装置ACT-8,利用旋涂法,将清漆涂布于8英寸的硅晶片上并进行预烘烤,然后使用惰性气体烘箱CLH-21CD-S(Koyo Thermo System(株)制),在氧浓度为20ppm以下的条件下,以3.5℃/分钟升温至190℃,于190℃进行1小时加热处理。在温度达到50℃以下时,取出晶片,缓慢冷却后,接着,使用热循环试验机(以下记为TC装置)(TABAI ESPEC(株)制),将于-45℃处理15分钟、并于125℃处理15分钟作为1个循环,进行500次循环的处理。取出晶片,在45质量%的氢氟酸中浸渍5分钟,由此将树脂组合物的膜从晶片剥离。将该膜切成宽度为1cm、长度为9cm的长条状,使用Tensilon RTM-100((株)Orientec制),在室温23.0℃、湿度45.0%RH的条件下以50mm/分钟的拉伸速度进行拉伸,进行断裂点伸长率的测定。针对每一被检物,对10个长条进行测定,并由结果求出较高的5个点的平均值。将断裂点伸长率的值为50%以上的情况评价为极为良好(A),将为30%以上且小于50%的情况评价为良好(B),将为15%以上且小于30%的情况评价为尚可(C),将小于15%的情况评价为不好(D)。
(4)金属密合性评价
在硅晶片上各自以100nm的厚度溅射钛、铜,然后通过电解电镀施以镀铜膜,制成在表面具有以2μm的厚度形成的金属材料层的基板(镀铜基板)。使用旋涂器(Mikasa(株)制),利用旋涂法,在该基板上涂布清漆,接着使用加热板(Dainippon Screen Mfg.Co.,Ltd.制D-SPIN),于120℃烘烤3分钟,最终制作了厚度为10μm的预烘烤膜。针对上述膜,使用清洁烘箱(Koyo Thermo System(株)制CLH-21CD-S),在氮气流下(氧浓度为20ppm以下),于140℃固化30分钟,接着进一步升温,于190℃固化1小时,得到树脂固化膜。使用单刃刀,在固化膜上以2mm的间隔切出10行10列的棋盘格状的切口。通过基于Cello-tape(注册商标)的剥离,对在100个格子中有多少个格子发生剥离进行计数,进行金属材料/树脂固化膜间的密合特性的评价。进而,接着使用TC装置,将于-45℃处理15分钟、并于125℃处理15分钟作为1个循环,进行500次循环的处理,然后进行上述剥离测试。针对任意基板,在剥离测试中均如下进行评价:将剥离的个数为0的情况评价为极为良好(A),将为1以上且小于20的情况评价为良好(B),将为20以上的情况评价为不好(D)。
(5)TC后的铜图案截面评价
准备在硅晶片上以150μm的间隔、5μm的厚度形成有直径为60μm的铜通孔图案的铜图案晶片,使用等离子体处理装置((株)日立高科技仪器制,SPC-100B+H),在氧流量为50sccm、压力为20Pa、输出功率为1200W、时间为60秒的条件下进行等离子体蚀刻。
使用旋涂器(Mikasa(株)制),利用旋涂法,在该基板上涂布清漆,接着使用加热板(Dainippon Screen Mfg.Co.,Ltd.制D-SPIN),于120℃烘烤3分钟,最终制作了3张厚度为10μm的预烘烤膜。针对这些膜,使用清洁烘箱(Koyo Thermo System(株)制CLH-21CD-S),在氮气流下(氧浓度为20ppm以下),于140℃固化30分钟,接着进一步升温,于190℃固化1小时,得到3片形成有树脂固化膜的铜图案基板。
针对该形成有树脂固化膜的铜图案基板,各自使用TC装置,将于-45℃处理15分钟、并于125℃处理15分钟作为1个循环,进行500次循环处理(以下记为);将于-45℃处理15分钟、并于150℃处理15分钟作为1个循环,进行500次循环处理(以下记为);将于-60℃处理15分钟、并于150℃处理15分钟作为1个循环,进行500次循环处理(以下记为)。针对在3种条件下处理后的基板,各自使用离子铣削装置(日立高科技(株)制IM4000)来切断截面,并使用扫描电子显微镜(SEM,日立高科技公司制S-3000N)进行截面观察。将在固化膜中没有裂纹、没有固化膜与铜通孔图案的剥离、没有铜通孔图案的聚集剥离(铜层与氧化铜层的剥离)的情况评价为合格,将经的处理而合格的情况评价为极为良好(A),将经的处理而合格的情况评价为良好(B),将经的处理而合格的情况评价为尚可(C),将在任意条件下均不合格的情况评价为不可(D)。
(合成例1)酸A的合成
在氮气流下,向250ml的三颈瓶中加入咪唑27.2g(0.4mol),并加入二氯甲烷100g,于室温搅拌。将其冷却至-5℃以下,以反应溶液的温度不超过0℃的方式,经1小时滴加下述液体,所述液体是使4,4’-二苯基醚二甲酸二酰氯29.5g(0.1mol)分散于100g的二氯甲烷中得到的。滴加后,于室温对反应溶液进一步搅拌3小时,将反应中产生的沉淀物过滤。用纯水将过滤后的沉淀物洗涤数次,用50℃的真空烘箱干燥100小时,得到下式所示的酸A。
[化学式31]
(合成例2)聚酰亚胺树脂(A-1)的合成
在干燥氮气流下,使2,2-双(3-氨基-4-羟基苯基)六氟丙烷(以下称为BAHF)(18.3g,0.05mol)、1,3-双(3-氨基丙基)四甲基二硅氧烷(0.62g,0.0025mol)、5-降冰片烯-2,3-二甲酸(0.82g,0.005mol)、溶解于NMP 125g中。向其中与NMP 25g一起加入4,4’-氧双邻苯二甲酸酐(13.95g,0.045mol),于60℃搅拌1小时,接着于180℃搅拌4小时。搅拌结束后,将溶液投入水3L中,得到白色沉淀。通过过滤收集该沉淀,用水洗涤3次后,用50℃的通风干燥机干燥3天,得到聚酰亚胺树脂(A-1)的粉末。通过上述方式得到的树脂的酰亚胺化率为97%。重均分子量为38,800,PDI为1.9。
(合成例3)聚酰胺树脂(A-2)的合成
在干燥氮气流下,使2,2-双(3-氨基-4-羟基苯基)六氟丙烷(以下称为BAHF)(15.6g,0.043mol)、RT-1000(7.5g,0.0075mol)、1,3-双(3-氨基丙基)四甲基二硅氧烷(0.62g,0.0025mol)溶解于NMP 100g中。向其中与NMP 25g一起加入酸A(13.51g,0.045mol)、5-降冰片烯-2,3-二甲酸(0.82g,0.005mol),于85℃反应3小时。反应结束后,冷却至室温,与NMP 25g一起加入乙酸(13.20g,0.25mol),于室温搅拌1小时。搅拌结束后,将溶液投入水1.5L中,得到白色沉淀。通过过滤收集该沉淀,用水洗涤3次后,用50℃的通风干燥机干燥3天,得到聚酰胺树脂(A-2)的粉末。重均分子量为32,600,PDI为1.9。
(合成例4)聚酰胺-聚酰亚胺共聚树脂(A-3)
在干燥氮气流下,使BAHF(14.6g,0.040mol)、RT-1000(7.5g,0.0075mol)溶解于NMP 100g中。向其中与NMP 10g一起加入酸A(11.26g,0.038mol),于85℃反应3小时。然后,与NMP 5g一起加入BAHF(1.0g,0.0025mol)、1,3-双(3-氨基丙基)四甲基二硅氧烷(0.62g,0.0025mol)、5-降冰片烯-2,3-二甲酸(0.82g,0.005mol),于85℃反应1小时,然后,与NMP5g一起加入4,4’-氧双邻苯二甲酸酐(2.33g,0.0075mol),于85℃反应1小时。反应结束后,冷却至室温,与NMP 25g一起加入乙酸(13.20g,0.25mol),于室温搅拌1小时。搅拌结束后,将溶液投入水1.5L中,得到白色沉淀。通过过滤收集该沉淀,用水洗涤3次后,用50℃的通风干燥机干燥3天,得到聚酰胺-聚酰亚胺共聚树脂(A-3)的粉末。通过上述方式得到的树脂的酰亚胺化率为70%。重均分子量为32,600,PDI为1.9。根据来自聚酰胺的酸A与来自聚酰亚胺·聚酰亚胺前体的4,4’-氧双邻苯二甲酸酐的装料比、酰亚胺化率的值,相对于聚酰胺与聚酰亚胺的结构单元合计100摩尔%而言,上述聚酰亚胺的结构单元的含量为12%。
(合成例5)酚醛树脂(A-4)的合成
向加入有四氢呋喃500ml、作为引发剂的仲丁基锂0.01摩尔的混合溶液中,以摩尔比3∶1的比例添加对叔丁氧基苯乙烯与苯乙烯共计20g,在搅拌3小时的同时使其发生聚合。聚合终止反应是向反应溶液中添加0.1摩尔甲醇来进行的。接着,为了将聚合物纯化,将反应混合物注入甲醇中,使沉降的聚合物干燥,结果得到白色聚合物。进而,溶解于丙酮400ml中,于60℃加入少量浓盐酸,搅拌7小时后注入水中,使聚合物沉淀,将对叔丁氧基苯乙烯脱保护而转化为羟基苯乙烯,进行洗涤干燥,结果以经纯化的对羟基苯乙烯与苯乙烯的共聚物即聚羟基苯乙烯树脂的形式得到酚醛树脂(A-4)。
(合成例6)聚酰亚胺前体(A-5)的合成
将4,4’-氧二邻苯二甲酸酐(155.1g,0.5mol)加入容量为21的可分离式烧瓶中,并加入甲基丙烯酸2-羟基乙酯125g和γ-丁内酯400ml,于室温下搅拌,一边搅拌一边加入吡啶81.5g,得到反应混合物。在由反应产生的放热结束后,放置冷却至室温,放置16小时。
接着,在用冰进行冷却下,一边对在γ-丁内酯180ml中溶解有二环己基碳二亚胺206.3g的溶液进行搅拌,一边经40分钟加入至反应混合物中,接着,一边对在γ-丁内酯350ml中悬浮有4,4’-二氨基二苯基醚(95.0g,0.48mol)的物质进行搅拌,一边经60分钟加入。进而,于室温搅拌2小时,然后,加入乙醇30ml,搅拌1小时,接着加入γ-丁内酯400ml。通过过滤将反应混合物中产生的沉淀物除去,得到反应液。将得到的反应液加入3L乙醇中,生成由粗聚合物形成的沉淀物。将生成的粗聚合物过滤分离,并溶解于四氢呋喃1.5L中,得到粗聚合物溶液。将得到的粗聚合物溶液滴加至28L的水中,使聚合物沉淀,将得到的沉淀物过滤分离,然后进行真空干燥,得到粉末状的聚酰亚胺前体(A-5)的粉末。通过上述方式得到的树脂的酰亚胺化率为14%。重均分子量为38,600,PDI为2.1。
(合成例7)聚酰胺-聚酰亚胺共聚树脂(A-6)的合成
在干燥氮气流下,使BAHF(14.6g,0.040mol)、RT-1000(7.5g,0.0075mol)溶解于NMP 100g中。向其中与NMP 10g一起加入酸A(13.06g,0.044mol),于85℃反应3小时。然后,与NMP 5g一起加入BAHF(1.0g,0.0025mol)、1,3-双(3-氨基丙基)四甲基二硅氧烷(0.62g,0.0025mol)、5-降冰片烯-2,3-二甲酸(0.82g,0.005mol),于85℃反应1小时后,与NMP 5g一起加入4,4’-氧双邻苯二甲酸酐(0.47g,0.0015mol),于85℃反应1小时。反应结束后,冷却至室温,与NMP 25g一起加入乙酸(13.20g,0.25mol),于室温搅拌1小时。搅拌结束后,将溶液投入水1.5L中,得到白色沉淀。通过过滤收集该沉淀,用水洗涤3次后,用50℃的通风干燥机干燥3天,得到聚酰胺-聚酰亚胺共聚树脂(A-6)的粉末。通过上述方式得到的树脂的酰亚胺化率为71%。重均分子量为32,300,PDI为1.9。根据来自聚酰胺的酸A与来自聚酰亚胺·聚酰亚胺前体的4,4’-氧双邻苯二甲酸酐的装料比、酰亚胺化率的值,相对于聚酰胺与聚酰亚胺的结构单元合计100摩尔%而言,上述聚酰亚胺的结构单元的含量为2%。
(合成例8)聚酰胺-聚酰亚胺共聚树脂(A-7)
在干燥氮气流下,使BAHF(14.6g,0.040mol)、RT-1000(7.5g,0.0075mol)溶解于NMP 100g中。向其中与NMP 10g一起加入酸A(6.76g,0.023mol),于85℃反应3小时。然后,与NMP 5g一起加入BAHF(1.0g,0.0025mol)、1,3-双(3-氨基丙基)四甲基二硅氧烷(0.62g,0.0025mol)、5-降冰片烯-2,3-二甲酸(0.82g,0.005mol),于85℃反应1小时后,与NMP 5g一起加入4,4’-氧双邻苯二甲酸酐(6.93g,0.023mol),于85℃反应1小时。反应结束后,冷却至室温,与NMP 25g一起加入乙酸(13.20g,0.25mol),于室温搅拌1小时。搅拌结束后,将溶液投入水1.5L中,得到白色沉淀。通过过滤收集该沉淀,用水洗涤3次后,用50℃的通风干燥机干燥3天,得到聚酰胺-聚酰亚胺共聚树脂(A-7)的粉末。通过上述方式得到的树脂的酰亚胺化率为82%。重均分子量为35,300,PDI为1.9。根据来自聚酰胺的酸A、与来自聚酰亚胺·聚酰亚胺前体的4,4’-氧双邻苯二甲酸酐的装料比、酰亚胺化率的值,相对于聚酰胺与聚酰亚胺的结构单元合计100摩尔%而言,上述聚酰亚胺的结构单元的含量为45%。
(合成例9)聚酰胺-聚酰亚胺共聚树脂(A-8)的合成
在干燥氮气流下,使BAHF(14.6g,0.040mol)、RT-1000(7.5g,0.0075mol)溶解于NMP 100g中。向其中与NMP 10g一起加入酸A(9.30g,0.03mol),于85℃反应3小时。然后,与NMP 5g一起加入BAHF(1.0g,0.0025mol)、1,3-双(3-氨基丙基)四甲基二硅氧烷(0.62g,0.0025mol)、5-降冰片烯-2,3-二甲酸(0.82g,0.005mol),于85℃反应1小时后,与NMP 5g一起加入4,4’-氧双邻苯二甲酸酐(9.30g,0.03mol),于85℃反应1小时。反应结束后,冷却至室温,与NMP 25g一起加入乙酸(13.20g,0.25mol),于室温搅拌1小时。搅拌结束后,将溶液投入水1.5L中,得到白色沉淀。通过过滤收集该沉淀,用水洗涤3次后,用50℃的通风干燥机干燥3天,得到聚酰胺-聚酰亚胺共聚树脂(A-6)的粉末。通过上述方式得到的树脂的酰亚胺化率为80%。重均分子量为35,500,PDI为1.9。根据来自聚酰胺的酸A与来自聚酰亚胺·聚酰亚胺前体的4,4’-氧双邻苯二甲酸酐的装料比、酰亚胺化率的值,相对于聚酰胺与聚酰亚胺的结构单元合计100摩尔%而言,上述聚酰亚胺的结构单元的含量为55%。
[实施例1~10、12~14、比较例6~8]
作为(a)树脂,使用上述树脂(A-1)~(A-3),针对各树脂(A-1)~(A-3)成分10g,以表1所示的规定量配合(b)成分、(c)成分、(d)成分、(e)成分、(f)成分,并加入20g的γ-丁内酯,制作清漆。
[比较例1]
代替(a)树脂成分而使用上述酚醛树脂(A-4),针对(A-4)成分10g,以表1所示的规定量配合(b)成分、(c)成分、(d)成分,加入20g的γ-丁内酯,制作清漆。
[实施例11]
作为(a)树脂,使用上述树脂(A-5),针对树脂(A-5)成分10g,以表1所示的规定量配合(b)成分、(c)成分、(d)成分,代替(c)萘醌二叠氮化合物而加入聚合引发剂(C-2)2.0g和光聚合性化合物(C-3)2.0g,并加入20g的γ-丁内酯,制作清漆。
[实施例15]
作为(a)树脂,使用上述树脂(A-5),针对树脂(A-5)成分10g,以表1所示的规定量配合(b)成分、(d)成分,并加入20g的γ-丁内酯,制作清漆。
[比较例9]
作为(a)树脂,使用上述树脂(A-5),针对树脂(A-5)成分10g,以表1所示的规定量配合(b)成分,并加入20g的γ-丁内酯,制作清漆。
将各实施例、比较例中得到的树脂组合物的特性结果示于表2中。
[表1]
(B-1)~(B-3)、(C-1)~(C-3)、(D-1)~(D-5)、(E-1)~(E-2)、(F)分别为下述化学式所示的化合物。
[化学式32]
[化学式33]
[化学式34]
[化学式35]
[化学式36]
附图标记说明
1 硅晶片
2 Al焊盘
3 钝化膜
4 绝缘膜
5 金属(Cr、Ti等)膜
6 金属布线(Al、Cu等)
7 绝缘膜
8 势垒金属
9 划片槽
10 焊料凸块
11 密封树脂
12 基板
13 绝缘膜
14 绝缘膜
15 金属(Cr、Ti等)膜
16 金属布线(Ag、Cu等)
17 金属布线(Ag、Cu等)
18 电极
19 密封树脂
20 支承基板(玻璃基板、硅晶片)
21 电极焊盘(Cu)
22 绝缘膜
23 金属布线(Cu)
24 Cu柱
25 焊料凸块
26 半导体芯片
27 TFT(薄膜晶体管)
28 布线
29 TFT绝缘层
30 平坦化层
31 ITO(透明电极)
32 基板
33 接触孔
34 绝缘层
Claims (25)
1.树脂组合物,其特征在于,含有(a)树脂、(b)抗氧化剂、(d)交联剂,其中,
所述(a)树脂包含选自聚酰亚胺前体、聚酰胺、聚酰亚胺、聚苯并噁唑、及它们的共聚物中的一种以上的树脂,
所述(d)交联剂是在一分子中具有酚式羟基、并且在所述酚式羟基的两个邻位具有分子量为40以上的取代基的交联剂。
2.如权利要求1所述的树脂组合物,其中,所述(a)树脂为具有酚式羟基的碱溶性树脂,所述树脂组合物还含有(c)萘醌二叠氮化合物。
3.如权利要求1或2所述的树脂组合物,其中,所述(d)交联剂是在一分子中具有3个以上酚式羟基的交联剂。
4.如权利要求1~3中任一项所述的树脂组合物,其中,所述(b)抗氧化剂为具有受阻酚结构的抗氧化剂。
5.如权利要求1~4中任一项所述的树脂组合物,其中,所述(b)抗氧化剂包含通式(1)表示的化合物,
[化学式1]
通式(1)中,R1表示氢原子或碳原子数2以上的烷基,R2表示碳原子数2以上的亚烷基;A表示包含碳原子数2以上的亚烷基、O原子、及N原子中的至少任一者的1~4价有机基团;k表示1~4的整数。
6.如权利要求1~5中任一项所述的树脂组合物,其中,所述(a)树脂具有通式(2)表示的结构单元,
[化学式2]
通式(2)中,R3~R6各自独立地表示碳原子数2~10的亚烷基,a、b及c各自表示1≤a≤20、0≤b≤20、0≤c≤20的范围内的整数,重复单元的排列可以为嵌段式也可以为无规式;并且,通式(2)中,*表示化学键。
7.如权利要求1~6中任一项所述的树脂组合物,其中,
所述(a)树脂至少包含聚酰胺与聚酰亚胺的共聚物,
所述聚酰胺具有来自具有脂肪族基团的二胺的结构单元,并且,相对于所有的来自二胺的结构单元100摩尔%而言,所述来自具有脂肪族基团的二胺的结构单元的含量在5~40摩尔%的范围内。
8.如权利要求1~7中任一项所述的树脂组合物,其中,
所述(a)树脂至少包含聚酰胺与聚酰亚胺的共聚物,
相对于所述聚酰胺与所述聚酰亚胺的结构单元合计100摩尔%而言,所述聚酰亚胺的结构单元的含量在2~50摩尔%的范围内。
9.如权利要求1~8中任一项所述的树脂组合物,所述树脂组合物还含有(e)通式(3)表示的化合物,相对于所述(a)树脂100质量份而言,所述(e)通式(3)表示的化合物的含量在0.5~15质量份的范围内,
[化学式3]
通式(3)中,R7~R9表示N原子、O原子或S原子中的任一者,R7~R9中的至少1个表示S原子;l表示0或1,m、n表示0~2的整数;R10~R12各自独立地表示氢原子或碳原子数1~20的有机基团。
10.如权利要求1~9中任一项所述的树脂组合物,所述树脂组合物还含有(f)具有下述通式(4)表示的结构单元的热交联剂,
[化学式4]
通式(4)中,R13及R14各自独立地表示氢原子或甲基;R15为具有碳原子数2以上的亚烷基的2价有机基团,直链状、支链状及环状均可。
11.树脂片材,其由权利要求1~10中任一项所述的树脂组合物形成。
12.固化膜,其是将权利要求1~10中任一项所述的树脂组合物进行固化而得到的。
13.固化膜,其是将权利要求11所述的树脂片材进行固化而得到的。
14.如权利要求12或13所述的固化膜,所述固化膜的断裂点伸长率为50%以上。
15.固化膜的浮凸图案的制造方法,其包括下述工序:
将权利要求2~10中任一项所述的树脂组合物涂布于基板上、或将权利要求11所述的树脂片材层压于基板上,并进行干燥而形成树脂膜的工序;
隔着掩模进行曝光的工序;
利用碱性溶液将照射部溶出或除去而进行显影的工序;及
对显影后的树脂膜进行加热处理的工序。
16.如权利要求15所述的固化膜的浮凸图案的制造方法,其中,将所述树脂组合物涂布于基板上并进行干燥而形成树脂膜的工序包括使用狭缝喷嘴涂布于基板上的工序。
17.半导体电子部件或半导体器件,其配置有权利要求12~14中任一项所述的固化膜作为铜金属的再布线间的层间绝缘膜。
18.如权利要求17所述的半导体电子部件或半导体器件,其中,所述再布线由经氧化处理的铜金属布线构成。
19.如权利要求17或18所述的半导体电子部件或半导体器件,其中,所述再布线为铜金属布线,铜金属布线的宽度及相邻布线彼此的间隔为5μm以下。
20.半导体电子部件或半导体器件,其在配置有硅芯片的密封树脂基板上配置有权利要求12~14中任一项所述的固化膜作为再布线间的层间绝缘膜。
21.如权利要求17~20所述的半导体电子部件或半导体器件,其中,所述再布线为铜金属布线,并且,介由凸块将半导体芯片与铜金属布线连接。
22.如权利要求17~21所述的半导体电子部件或半导体器件,其中,随着权利要求17中记载的再布线层接近半导体芯片,金属布线的宽度及相邻布线彼此的间隔变窄。
23.如权利要求17~22所述的半导体电子部件或半导体器件,其中,权利要求17中记载的层间绝缘膜的厚度随着接近半导体芯片而变薄。
24.有机EL显示装置,其具备权利要求12~14中任一项所述的固化膜。
25.半导体电子部件或半导体器件的制造方法,其包括下述工序:
在配置有临时粘贴材料的支承基板上配置权利要求12~14中任一项所述的固化膜作为再布线间的层间绝缘膜的工序;
在层间绝缘膜上配置硅芯片和密封树脂的工序;以及
然后,将配置有临时粘贴材料的支承基板与再布线进行剥离的工序。
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