CN107556480B - 含硅酮骨架高分子化合物、光固化性树脂组合物、光固化性干膜、积层体、及图案形成方法 - Google Patents
含硅酮骨架高分子化合物、光固化性树脂组合物、光固化性干膜、积层体、及图案形成方法 Download PDFInfo
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- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- FAYMLNNRGCYLSR-UHFFFAOYSA-M triphenylsulfonium triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 FAYMLNNRGCYLSR-UHFFFAOYSA-M 0.000 description 1
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- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
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Classifications
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Abstract
本发明所要解决的问题在于,提供一种含硅酮骨架高分子化合物、包含该高分子化合物的光固化性树脂组合物、其光固化性干膜、使用它们的积层体、及图案形成方法,所述硅酮骨架高分子化合物能够以厚膜容易地实行微细图案的形成,并且,能够形成一种作为电性/电子零件保护用皮膜、或基板接合用皮膜等的可靠性优良的固化物层(固化皮膜),其耐开裂性、及对于基板、电子零件或半导体元件等、尤其是对在电路基板中使用的基材的密接性等各种膜特性优良。本发明的解决问题的技术方案是一种含硅酮骨架高分子化合物,其由下述式(1)表示,包含硅酮骨架且重均分子量为3000~500000。
Description
技术领域
本发明涉及一种新颖的含硅酮骨架高分子化合物及光固化性树脂组合物、其干膜、使用它们的图案形成方法、以及使用该组合物或干膜的积层体,所述含硅酮骨架高分子化合物例如可用作电性/电子零件保护用皮膜的材料或基板接合用皮膜的材料。
背景技术
目前,作为具有感光性的半导体元件保护膜或多层印刷基板用绝缘膜,使用感光性聚酰亚胺组合物或感光性环氧树脂组合物、感光性硅酮组合物等。作为这种适用于基板、电路保护的感光性材料,提出其中的可挠性尤佳的感光性硅酮组合物(专利文献1)。此感光性硅酮组合物可在低温下固化,并且,可形成耐湿粘合性等可靠性良好的皮膜,但存在对于N-甲基-2-吡咯烷酮等溶解力强的光阻剥离液等的耐化学品性差的问题。
对此,提出以含硅亚苯基骨架的硅酮型高分子化合物为主成分的感光性硅酮组合物(专利文献2)。作为前述感光性硅酮组合物,对于光阻剥离液等的耐化学品性提升,但当热循环试验(以-25℃下保持10分钟、125℃下保持10分钟的方式反复进行1000次循环)时,存在固化物从基板剥离、或在固化物上形成裂纹等问题,希望进一步提升可靠性。
现有技术文献
专利文献
专利文献1:日本特开2002-88158号公报。
专利文献2:日本特开2008-184571号公报。
发明内容
本发明是鉴于前述情况而完成的,其目的在于提供一种含硅酮骨架高分子化合物、含有该高分子化合物的光固化性树脂组合物、其光固化性干膜、使用它们的积层体及图案形成方法,所述含硅酮骨架高分子化合物能以厚膜容易地形成微细图案,并且,能够形成一种作为电性/电子零件保护用皮膜、或基板接合用皮膜等的可靠性优良的固化物层(固化皮膜),其耐开裂性及对于基板、电子零件或半导体元件等、尤其是电路基板中使用的基材的密接性等各种膜特性优良。
为了解决前述课题,根据本发明,提供一种含硅酮骨架高分子化合物,其由下述式(1)表示,包含硅酮骨架且重均分子量为3000~500000,
式(1)中,R1~R4各自独立地表示碳原子数1~8的一价烃基,m与n各自独立地为0~300的整数,此外,a、b都是正数且a+b=1,X是选自由下述通式(2)、(3)、(4)、(5)及(6)表示的二价基团的群组中的连结基,当将由下述通式(2)表示的单元的摩尔数设为c、将由下述通式(3)表示的单元的摩尔数设为d、将由下述通式(4)表示的单元的摩尔数设为e、将由下述通式(5)表示的单元的摩尔数设为f、将由下述通式(6)表示的单元的摩尔数设为g时,c、d、e、g为0或正数,f为正数,其中,c+d+e为正数;
式(2)、式(3)中,V、Z是选自下式中的任一个的2价有机基,
j和p为0或1,此外,R5和R8表示氢原子或甲基,h和k为0~7的整数,R6、R7、R9及R10各自独立地为碳数1~4的烷基或烷氧基,彼此不同或相同,i和r为0、1、及2中的任一个,
式(4)中,R11表示氢原子或甲基,q为0~7的整数,
式(5)中,Y为二价有机基,R12各自独立地表示氢原子或碳原子数1~8的一价烃基,一部分被卤素原子取代或不被卤素原子取代,彼此不同或相同,R13各自独立地表示碳原子数1~8的亚烷基,彼此不同或相同,此外,Rx是单键或与Rxx闭环而形成环结构的基团,Rxx是氢原子或碳原子数1~8的一价烃基,
式(6)中,t与u各自独立地为0~300的整数,此外,R14表示氢原子或甲基,R15与R16各自独立地表示碳原子数1~8的一价烃基,s为0~7的整数。
此种本发明的含硅酮骨架高分子化合物,作为赋予充分的膜形成能力的成分而发挥功能,由使用它的组合物获得的光固化性树脂层,对于基板、电子零件或半导体元件等的密接性优良,具有良好的图案形成能力、耐开裂性及优良的耐热性。
此外,这种情况下,前述通式(5)优选为下述式(5-1)。
式(5-1)中,Y、R12及R13与上文前述相同;R17各自独立地表示碳原子数1~8的亚烷基,彼此不同或相同;R18各自独立地表示氢原子或碳原子数1~8的一价烃基,一部分被卤素原子取代或不被卤素原子取代,彼此不同或相同。
只要为这种含硅酮骨架高分子化合物,则容易合成,所以优选。
此外,本发明中,提供一种光固化性树脂组合物,其特征在于,含有前述含硅酮骨架高分子化合物(A)、及在190~500nm的光下会分解而产生酸的光致产酸剂(B)。
只要为这种光固化性树脂组合物,则容易以厚膜形成垂直性优良的微细图案,能够形成一种作为电性/电子零件保护用皮膜、或基板接合用皮膜等的可靠性优良的固化物层(固化皮膜),其对于基板、电子零件或半导体元件、尤其是电路基板中使用的基材的密接性、机械特性及电绝缘性优良。
此外,这种情况下,更优选为含有交联剂(C)。
如此,只要为含有交联剂(C)的光固化性树脂组合物,则能更容易形成图案,且能进一步提高固化物的强度。
此外,这种情况下,前述交联剂(C)可为选自经甲醛或甲醛-醇改性后的胺缩合物、1分子中平均具有2个以上羟甲基或烷氧基羟甲基的酚化合物、及1分子中平均具有2个以上环氧基的环氧化合物中的任一种以上。
只要为此种交联剂(C),则能进一步提高固化物的强度,所以优选。
此外,这种情况下,更优选含有溶剂(D)。
这样,因含有溶剂(D),所以光固化性树脂组合物的涂布性提升,所以优选。
此外,这种情况下,更优选为含有碱性化合物(E)。
这样,因含有碱性化合物(E),所以解析度提升,能抑制曝光后的灵敏度变化,减小基板依赖性或环境依赖性,提升曝光裕度或图案形状。
此外,本发明中,提供一种光固化性干膜,其特征在于:是前述光固化性树脂组合物涂布在支撑膜上并经过干燥而成。
此种光固化性干膜的光固化性树脂层,可提供一种对于基板、电子零件或半导体元件、尤其是电路基板中使用的基材的密接性、机械特性、电绝缘性及耐开裂性优良的固化物层。
此外,本发明中,提供一种积层体,其特征在于,在具有开口宽度为10~100μm且深度为10~120μm的槽和孔中的任一者或两者的基板上,形成有前述光固化性树脂组合物的固化物层、或前述光固化性干膜中的光固化性树脂层的固化物层。
此种积层体的固化物层与基板的密接性优良,此外,当使用此种具有凹凸的基板时也具有高平坦性。
此外,本发明中提供一种图案形成方法,其特征在于,包括如下步骤:
(i)将前述光固化性树脂组合物涂布在基板上,从而在前述基板上形成光固化性树脂层;
(ii)隔着光掩模对前述光固化性树脂层进行曝光;以及,
(iii)在进行曝光后的加热处理后,利用显影液进行显影而溶解除去非曝光部,从而形成图案。
此外,本发明中提供一种图案形成方法,其特征在于,包括如下步骤:
(i)使前述光固化性干膜密接于基板,从而在前述基板上形成光固化性树脂层;
(ii)隔着光掩模对前述光固化性树脂层进行曝光;以及,
(iii)在进行曝光后的加热处理后,利用显影液进行显影而溶解除去非曝光部,从而形成图案。
这样,使用本发明的利用光固化性树脂组合物或光固化性干膜的图案形成方法,能以厚膜容易地形成微细图案。
此外,这种情况下,更优选为包括如下步骤:(iv)以100~250℃的温度,对根据显影而形成图案的皮膜进行后固化。
利用此种后固化,能提高光固化性树脂组合物的交联密度,除去残存的挥发成分,从而进一步提升对于基板等的密接力、耐热性、强度、电特性及接合强度。
此外,这种情况下,优选为,前述基板具有开口宽度为10~100μm且深度为10~120μm的槽和孔中的任一者或两者。
这样,本发明的光固化性树脂组合物或光固化性干膜,适宜用于在具有凹凸的基板上形成固化物层。
此外,前述光固化性树脂组合物可作为电性/电子零件保护用皮膜的材料。
此外,前述光固化性树脂组合物可作为用于将2个基板接合的基板接合用皮膜的材料。
本发明的光固化性树脂组合物的密接性或耐开裂性等各种膜特性优良,因此,可用作电性/电子零件保护用皮膜的材料、或基板接合用皮膜的材料。
根据本发明的含硅酮骨架高分子化合物、及使用该化合物的光固化性树脂组合物或光固化性干膜,能以厚膜容易地形成微细图案,且作为感光性材料表现出充分的特性,且该固化物层对于基板、电子零件或半导体元件、尤其是电路基板中使用的基材的密接性、机械特性及电绝缘性优良,其作为绝缘保护膜的可靠性高,而且能防止保护膜产生裂纹,因此,适宜用于电路基板、半导体元件、显示元件等的各种电性/电子零件保护用皮膜的形成材料或基板接合用皮膜的形成材料。此外,使用本发明的光固化性树脂组合物或光固化性干膜而制造的积层体的固化物层与基板的密接性优良,而且具有高平坦性。
具体实施方式
为了达成前述目的,本发明人反复进行悉心研究,结果发现:一种含硅酮骨架高分子化合物,其是包含硅酮骨架的高分子化合物,在由下述通式(1)表示的分子中具有交联基或产生交联反应的反应点且重均分子量为3000~500000,所述含硅酮骨架高分子化合物作为赋予充分的膜形成能力的成分而发挥功能,由使用它的组合物获得的光固化性树脂层,能在广泛的膜厚范围内形成皮膜,能够形成一种对于基板、电子零件或半导体元件等的密接性优良、具有良好的图案形成能力、优良的耐开裂性、耐热性、电绝缘性、作为绝缘保护膜的可靠性的固化物层,且可良好地作为电性/电子零件保护用皮膜或基板接合用皮膜,从而完成本发明。
因此,本发明提供一种下文所述的新颖的含硅酮骨架高分子化合物、光固化性树脂组合物、其光固化性干膜、使用它们的积层体、及图案形成方法。
以下,对于本发明的含硅酮骨架高分子化合物、光固化性树脂组合物、其光固化性干膜、使用它们的积层体、及图案形成方法进行详细说明,但本发明并不限于此。
<含硅酮骨架高分子化合物>
本发明的含硅酮骨架高分子化合物(本发明的光固化性树脂组合物中的(A)成分),其由下述式(1)表示,包含硅酮骨架且重均分子量为3000~500000。
式(1)中,R1~R4各自独立地表示碳原子数1~8的一价烃基。m与n各自独立地为0~300的整数。此外,a、b都是正数且a+b=1。X是选自由下述通式(2)、(3)、(4)、(5)及(6)表示的二价基团的群组中的连结基,当将由下述通式(2)表示的单元的摩尔数设为c、将由下述通式(3)表示的单元的摩尔数设为d、将由下述通式(4)表示的单元的摩尔数设为e、将由下述通式(5)表示的单元的摩尔数设为f、将由下述通式(6)表示的单元的摩尔数设为g时,c、d、e、g为0或正数,f为正数。其中,c+d+e为正数。
式(2)、式(3)中,V、Z是选自下式中的任一个的2价有机基,
j和p为0或1。此外,R5和R8表示氢原子或甲基,h和k为0~7的整数。R6、R7、R9及R10各自独立地为碳数1~4的烷基或烷氧基,彼此不同或相同。i和R为0、1、及2中的任一个。
式(4)中,R11表示氢原子或甲基,q为0~7的整数。
式(5)中,Y为二价有机基,R12各自独立地表示氢原子或碳原子数1~8的一价烃基,一部分可被卤素原子取代或不被卤素原子取代,彼此不同或相同。R13各自独立地表示碳原子数1~8的亚烷基,彼此不同或相同。此外,Rx是单键或与Rxx闭环而形成环结构的基团,Rxx是氢原子或碳原子数1~8的一价烃基。
式(6)中,t与u各自独立地为0~300的整数。此外,R14表示氢原子或甲基。R15与R16各自独立地表示碳原子数1~8的一价烃基。s为0~7的整数。
该本发明的含硅酮骨架高分子化合物((A)成分)作为赋予膜形成能力的成分而发挥功能。此外,获得的树脂膜赋予对于积层体、基板等的良好的密接性、良好的图案形成能力、耐开裂性及耐热性。另外,前述由通式(1)表示的含硅酮骨架高分子化合物的分子中具有环氧基、羟基等交联基或产生交联反应的反应点。
本发明的含硅酮骨架高分子化合物是如下聚合物,其含有前述由式(1)表示的重复单元,以四氢呋喃作为洗提溶剂且利用GPC测定出的聚苯乙烯换算的重均分子量为3000~500000,优选5000~200000。a、b都是正数且a+b=1。优选0.05≤a≤0.8,尤其优选0.1≤a≤0.7,优选0.2≤b≤0.95,尤其优选0.3≤b≤0.9。各单元可无规地键合,也可作为嵌段聚合物键合。此外,前述式(1)中,硅酮(硅氧烷)含有率优选30~80重量%。
前述式(1)中,m与n各自独立地为0~300的整数,m优选0~200,尤其优选0~100,n优选0~200,尤其优选0~100。此外,X是选自前述式(2)、(3)、(4)、(5)及(6)表示的二价基团的群组中的连结基,当将前述式(2)表示的单元的摩尔数设为c、将由前述式(3)表示的单元的摩尔数设为d、将由前述式(4)表示的单元的摩尔数设为e、将由前述式(5)表示的单元的摩尔数设为f、将由前述式(6)表示的单元的摩尔数设为g时,c、d、e、g为0或正数,f为正数。其中,c+d+e为正数。
该情况下,优选为,0≤c/硅酮树脂(A)中所含的以X所示的连结基的摩尔数(以下,称为X的摩尔数)≤0.6、0≤d/X的摩尔数≤0.8、0≤e/X的摩尔数≤0.6、0<f/X的摩尔数≤0.8、0≤g/X的摩尔数≤0.6,更优选为,0<c/X的摩尔数≤0.4、0<d/X的摩尔数≤0.7、0<e/X的摩尔数≤0.4、0.1≤f/X的摩尔数≤0.6、0≤g/X的摩尔数≤0.4。其中,c+d+e+f+g/X的摩尔数=1。另外,前述连结基可以无规或嵌段的任一种键合方式键合。
R1~R4各自独立地为碳原子数1~8、优选1~6的一价烃基,可列举烷基、环烷基、芳基等,可列举例如甲基、乙基、丙基、己基、环己基、及苯基等。其中,甲基及苯基因原料容易获得,所以优选。
通式(2)及(3)中,R6、R7、R9及R10分别独立地为碳数1~4的烷基或烷氧基,可列举例如甲基、乙基、丙基、丁基、甲氧基、乙氧基、丙氧基、丁氧基。
通式(5)中,Y为二价有机基。另外,本发明中的“二价有机基”是指含有碳原子的二价基。作为Y,具体而言可列举以下的有机基。
前述式中,R各自独立地表示氢原子或甲基。
其中,作为Y,优选选择以下的任一种有机基。
另外,前述有机基也可利用卤素原子(氟、氯、溴、碘)取代骨架中的氢原子。
R12各自独立地表示氢原子或碳原子数1~8的一价烃基,一部分被卤素原子取代或不被卤素原子取代。作为此R12,可列举与R1~R4所例示的一价烃基相同的元素,或其一部分被卤素原子(氯、溴、氟、碘)取代的元素。R13各自独立地表示碳原子数1~8的亚烷基,可列举例如亚甲基、亚乙基、亚丙基、亚丁基等。
此外,通式(5)中,Rx是单键或与Rxx闭环而形成环结构的基团,Rxx是氢原子或碳原子数1~8的一价烃基。作为Rx与Rxx闭环而得的环结构,可列举以下结构。另外,以下的各式中,左侧的2个键与式(5)中的含氮五元环键合而成为环结构。
其中,优选为选择
尤其优选为,通式(5)是下述式(5-1)所示的骨架。
式(5-1)中,Y、R12与R13与上文前述相同。R17各自独立地表示碳原子数1~8的亚烷基,彼此不同或相同。R18各自独立地表示氢原子或碳原子数1~8的一价烃基,一部分被卤素原子取代或不被卤素原子取代,彼此不同或相同。
此外,本发明的含硅酮骨架高分子化合物优选将双烯丙基二酰亚胺骨架键合于分子中或端基而成的化合物。
通式(6)中,R15与R16各自独立地表示碳原子数1~8的一价烃基,可列举与R1~R4例示的一价烃基相同的元素。t与u各自独立地为0~300的整数,t优选0~200,尤其优选0~100,u优选0~200,尤其优选0~100。此外,R14表示氢原子或甲基,s为0~7的整数。
[含硅酮骨架高分子化合物的制造方法]
本发明的含硅酮骨架高分子化合物,可通过使用选自由下述通式(7)、下述通式(8)、下述通式(9)、下述通式(10)、下述通式(11)、下述通式(12)及下述通式(13)表示的化合物中的化合物,在存在金属催化剂的条件下进行加成聚合而制造。
式(8)中,R1~R4各自独立地表示碳原子数1~8的一价烃基。m与n各自独立地为0~300的整数。
式(9)、式(10)中,V、Z是选自下式中的任一个的2价有机基,
j和p为0或1。此外,R5和R8表示氢原子或甲基,h和k为0~7的整数。R6、R7、R9及R10各自独立地为碳数1~4的烷基或烷氧基,彼此不同或相同。i和R为0、1、及2中的任一个。
式(11)中,R11表示氢原子或甲基,q为0~7的整数。
式(12)中,Y为二价有机基,R12各自独立地表示氢原子或碳原子数1~8的一价烃基,一部分被卤素原子取代或不被卤素原子取代,彼此不同或相同。R13各自独立地表示碳原子数1~8的亚烷基,彼此不同或相同。此外,Rx是单键或与Rxx闭环而形成环结构的基团,Rxx是氢原子或碳原子数为1~8的一价烃基。
式(13)中,t与u各自独立地为0~300的整数。此外,R14表示氢原子或甲基。R15与R16各自独立地表示碳原子数1~8的一价烃基。s为0~7的整数。
金属催化剂可使用例如铂(包括铂黑)、铑、钯等铂族金属单质;H2PtCl4·xH2O、H2PtCl6·xH2O、NaHPtCl6·xH2O、KHPtCl6·xH2O、Na2PtCl6·xH2O、K2PtCl4·xH2O、PtCl4·xH2O、PtCl2、Na2HPtCl4·xH2O(式中,x优选0~6的整数,尤其优选0或6)等氯化铂、氯铂酸及氯铂酸盐;醇改性氯铂酸(例如,美国专利第3,220,972号中记载);氯铂酸与烯烃的络合物(例如,美国专利第3,159,601号说明书、美国专利第3,159,662号说明书、及美国专利第3,775,452号说明书中记载);使铂黑或钯等铂族金属附载于氧化铝、二氧化硅、碳等载体而成的物质;铑-烯烃络合物;三(三苯基膦)氯化铑(所谓威尔金森催化剂);以及,氯化铂、氯铂酸或氯铂酸盐与含乙烯基硅氧烷(尤其是含乙烯基环状硅氧烷)的络合物。
催化剂的使用量是催化剂量,通常,作为铂族金属,相对于反应聚合物的总量优选0.001~0.1重量%。前述聚合反应中,可根据需要使用溶剂。作为溶剂,例如优选甲苯、二甲苯等烃系溶剂。作为前述聚合条件,从催化剂不会失活且能在短时间内完成聚合的观点出发,聚合温度例如优选40~150℃,尤其优选60~120℃。聚合时间可根据聚合物的种类及数量而决定,但为了防止湿气介入聚合系统中,优选以约0.5~100小时结束,尤其优选以0.5~30小时结束。这样结束聚合反应后,当使用溶剂时,通过馏除该溶剂,可获得本发明的前述由式(1)表示的含硅酮骨架高分子化合物(硅酮树脂)。
反应方法虽无特别限制,例如,当使由式(7)表示的化合物、由式(8)表示的化合物、由式(9)表示的化合物、由式(10)表示的化合物、由式(12)表示的化合物反应时,可首先将由式(9)、式(10)及式(12)表示的化合物混合并加热后,向前述混合液中添加金属催化剂,然后以0.1~5小时滴加由式(7)及式(8)表示的化合物。
关于各化合物的调配比,可以如下方式进行调配:对于由前述式(7)及式(8)表示的化合物所具有的氢硅烷基的摩尔数的合计、与由前述式(9)、前述式(10)、前述式(11)、前述式(12)及式(13)表示的化合物所具有的烯基的摩尔数的合计而言,氢硅烷基的合计摩尔数相对于烯基的合计摩尔数为0.67~1.67,优选0.83~1.25。聚合物的重均分子量可通过使用邻烯丙基苯酚等单烯丙基化合物、或、三乙基氢硅烷等单氢硅烷、单氢硅氧烷作为分子量调节剂而控制。
<光固化性树脂组合物>
本发明的光固化性树脂组合物含有前述含硅酮骨架高分子化合物(A)及在190~500nm光的作用下会分解而产生酸的光致产酸剂(B)。此种光固化性树脂组合物能在广泛的膜厚范围内形成皮膜,能利用后述的图案形成方法形成微细且垂直性优良的图案。此外,使用利用此种光固化性树脂组合物及其干膜的图案形成方法而获得的固化皮膜的图案性、耐热性、电绝缘性、作为绝缘保护膜的可靠性、尤其是与基板等的密接性优良。
[光致产酸剂(B)]
作为光致产酸剂(B),可列举在190~500nm波长的光照射下产生酸,且其成为固化催化剂的类型。本发明的树脂组合物的产酸剂的相容性优良,所以能使用广泛的产酸剂。作为此种产酸剂,可列举例如鎓盐、重氮甲烷衍生物、乙二肟衍生物、β-酮砜衍生物、二砜衍生物、硝基苄基磺酸酯衍生物、磺酸酯衍生物、酰亚胺基磺酸酯衍生物、肟磺酸酯衍生物、亚氨基磺酸酯衍生物、三嗪衍生物等。
作为前述鎓盐,可列举例如由下述通式(14)表示的化合物。
(R19)vM+K- (14)
式(14)中,R19表示可具有取代基的碳数1~12的直链状、支链状或环状的烷基、碳数6~12的芳基或碳数7~12的芳烷基,M+表示碘鎓或锍,K-表示非亲核性反离子,v表示2或3。
前述R19中,作为可具有取代基的烷基,可列举例如甲基、乙基、丙基、丁基、环己基、2-氧代环己基、降冰片基、金刚烷基等。此外,作为可具有取代基的芳基,可列举例如苯基;邻甲氧基苯基、间甲氧基苯基或对甲氧基苯基、乙氧基苯基、间叔丁氧基苯基或对叔丁氧基苯基等烷氧基苯基:2-甲基苯基、3-甲基苯基或4-甲基苯基、乙基苯基、4-叔丁基苯基、4-丁基苯基、二甲基苯基等烷基苯基等。此外,作为可具有取代基的芳烷基,例如,苄基、苯乙基等各个基团。
作为K-的非亲核性反离子,可列举氯化物离子、溴化物离子等卤化物离子;三氟甲烷磺酸酯、1,1,1-三氟乙烷磺酸酯、九氟丁烷磺酸酯等氟代烷基磺酸酯;甲苯磺酸酯、苯磺酸酯、4-氟苯磺酸酯、1,2,3,4,5-五氟苯磺酸酯等芳基磺酸酯;甲磺酸酯、丁烷磺酸酯等烷基磺酸酯等。
作为重氮甲烷衍生物,可列举下述由通式(15)表示的化合物。
式(15)中,R20可相同也可不同,为碳数1~12的直链状、支链状或环状的烷基或卤代烷基、可具有取代基的碳数6~12的芳基或卤代芳基、或碳数7~12的芳烷基。
前述R20中,作为烷基,可列举例如甲基、乙基、丙基、丁基、戊基、环戊基、环己基、降冰片基、金刚烷基等。作为卤代烷基,可列举例如三氟甲基、1,1,1-三氟乙基、1,1,1-三氯乙基、九氟丁基等。
作为可具有取代基的芳基,可列举例如苯基;邻甲氧基苯基、间甲氧基苯基或对甲氧基苯基、乙氧基苯基、间叔丁氧基苯基或对叔丁氧基苯基等烷氧基苯基;2-甲基苯基、3-甲基苯基或4-甲基苯基、乙基苯基、4-叔丁基苯基、4-丁基苯基、二甲基苯基等烷基苯基等。作为卤代芳基,可列举例如氟苯基、氯苯基、1,2,3,4,5-五氟苯基等。作为芳烷基,可列举例如苄基、苯乙基等。
作为(B)成分即光致产酸剂,具体而言,可列举例如三氟甲磺酸二苯基碘鎓、三氟甲磺酸(对叔丁氧基苯基)苯基碘鎓、对甲苯磺酸二苯基碘鎓、对甲苯磺酸(对叔丁氧基苯基)苯基碘鎓、三氟甲磺酸三苯基锍、三氟甲磺酸(对叔丁氧基苯基)二苯基锍、三氟甲磺酸双(对叔丁氧基苯基)苯基锍、三氟甲磺酸三(对叔丁氧基苯基)锍、对甲苯磺酸三苯基锍、对甲苯磺酸(对叔丁氧基苯基)二苯基锍、对甲苯磺酸双(对叔丁氧基苯基)苯基锍、对甲苯磺酸三(对叔丁氧基苯基)锍、九氟代丁烷磺酸三苯基锍、丁烷磺酸三苯基锍、三氟甲磺酸三甲基锍、对甲苯磺酸三甲基锍、三氟甲磺酸环己基甲基(2-氧代环己基)锍、对甲苯磺酸环己基甲基(2-氧代环己基)锍、三氟甲磺酸二甲基苯基锍、对甲苯磺酸二甲基苯基锍、三氟甲磺酸二环己基苯基锍、对甲苯磺酸二环己基苯基锍、双(4-叔丁基苯基)碘鎓六氟磷酸盐、二苯基(4-硫代苯氧基苯基)锍六氟锑酸盐等鎓盐;双(苯磺酰基)重氮甲烷、双(对甲苯磺酰基)重氮甲烷、双(二甲苯磺酰基)重氮甲烷、双(环己基磺酰基)重氮甲烷、双(环戊基磺酰基)重氮甲烷、双(正丁基磺酰基)重氮甲烷、双(异丁基磺酰基)重氮甲烷、双(仲丁基磺酰基)重氮甲烷、双(正丙基磺酰基)重氮甲烷、双(异丙基磺酰基)重氮甲烷、双(叔丁基磺酰基)重氮甲烷、双(正戊基磺酰基)重氮甲烷、双(异戊基磺酰基)重氮甲烷、双(仲戊基磺酰基)重氮甲烷、双(叔戊基磺酰基)重氮甲烷、1-环己基磺酰基-1-(叔丁基磺酰基)重氮甲烷、1-环己基磺酰基-1-(叔戊基磺酰基)重氮甲烷、1-叔戊基磺酰基-1-(叔丁基磺酰基)重氮甲烷等重氮甲烷衍生物;双-邻(对甲苯磺酰基)-α-二甲基乙二肟、双-邻(对甲苯磺酰基)-α-二苯基乙二肟、双-邻(对甲苯磺酰基)-α-二环己基乙二肟、双-邻(对甲苯磺酰基)-2,3-戊二酮乙二肟、双-(对甲苯磺酰基)-2-甲基-3,4-戊二酮乙二肟、双-邻(正丁基磺酰基)-α-二甲基乙二肟、双-邻(正丁基磺酰基)-α-二苯基乙二肟、双-邻(正丁基磺酰基)-α-二环己基乙二肟、双-邻(正丁基磺酰基)-2,3-戊二酮乙二肟、双-邻(正丁基磺酰基)-2-甲基-3,4-戊二酮乙二肟、双-邻(甲基磺酰基)-α-二甲基乙二肟、双-邻(三氟甲基磺酰基)-α-二甲基乙二肟、双-邻(1,1,1-三氟乙基磺酰基)-α-二甲基乙二肟、双-邻(叔丁基磺酰基)-α-二甲基乙二肟、双-邻(全氟辛基磺酰基)-α-二甲基乙二肟、双-邻(环己基磺酰基)-α-二甲基乙二肟、双-邻(苯磺酰基)-α-二甲基乙二肟、双-邻(对氟代苯磺酰基)-α-二甲基乙二肟、双-邻(对叔丁基苯磺酰基)-α-二甲基乙二肟、双-邻(二甲苯磺酰基)-α-二甲基乙二肟、双-邻(樟脑磺酰基)-α-二甲基乙二肟等乙二肟衍生物;α-(苯锍氧基亚氨基)-4-甲基苯基乙腈等肟磺酸酯衍生物;2-环己基羰基-2-(对甲苯磺酰基)丙烷、2-异丙基羰基-2-(对甲苯磺酰基)丙烷等β-酮砜衍生物;二苯基二砜、二环己基二砜等二砜衍生物;对甲苯磺酸2,6-二硝基苄基酯、对甲苯磺酸2,4-二硝基苄基酯等硝基苄基磺酸酯衍生物;1,2,3-三(甲烷磺酰氧基)苯、1,2,3-三(三氟甲烷磺酰氧基)苯、1,2,3-三(对甲苯磺酰基氧基)苯等磺酸酯衍生物;酞酰亚胺基三氟甲烷磺酸酯、酞酰亚胺基甲苯磺酸酯、5-降冰片烯-2,3-二甲酰亚胺基三氟甲烷磺酸酯、5-降冰片烯-2,3-二甲酰亚胺基甲苯磺酸酯、5-降冰片烯-2,3-二甲酰亚胺基正丁基磺酸酯、正三氟甲烷磺酰氧基萘基酰亚胺等酰亚胺基磺酸酯衍生物等。
另外,可列举(5-(4-甲基苯基)磺酰基氧基亚氨基-5H-噻吩-2-亚基)-(2-甲基苯基)乙腈、(5-(4-(4-甲基苯基磺酰基氧基)苯基磺酰基氧基亚氨基)-5H-噻吩-2-亚基)-(2-甲基苯基)-乙腈等亚氨基磺酸酯、或2-甲基-2[(4-甲基苯基)磺酰基]-1-[(4-甲硫基)苯基]-1-丙烷等。其中,适宜使用酰亚胺基磺酸酯类或亚氨基磺酸酯类、肟磺酸酯类等。
关于前述光致产酸剂(B)的调配量,从光固化性的观点出发,相对于含硅酮骨架高分子化合物(A)100重量份,优选0.05~20重量份,尤其优选0.05~5重量份。若光致产酸剂(B)的量在0.05重量份以上,则不会因酸的产生量不足而无法充分进行交联反应,所以优选。此外,若在20重量份以下,则能抑制产酸剂自身的吸光度增大,不会产生透明性下降的问题,所以优选。
[交联剂(C)]
另外,本发明的光固化性树脂组合物优选含有交联剂(C)。本发明中使用的(C)成分是用于与上文所述(A)成分的式(3)中的酚基、或R9及/或R10的烷氧基发生缩合反应而使得容易形成图案的成分,且能进一步提高固化物的强度。作为此种(C)成分,优选重均分子量为150~10000,尤其优选重均分子量为200~3000的树脂。若重均分子量在150以上,则能获得充分的光固化性,若在10000以下,则不会令组合物的固化后的耐热性变差,所以优选。
此外,交联剂(C)优选选自经甲醛或甲醛-醇改性后的胺缩合物、1分子中平均具有2个以上羟甲基或烷氧基羟甲基的酚化合物、及1分子中平均具有2个以上环氧基的环氧化合物中的任一种以上。
作为前述(C)成分即经甲醛或甲醛-醇改性后的胺缩合物,可列举例如经甲醛或甲醛-醇改性后的三聚氰胺缩合物、或经甲醛或甲醛-醇改性后的尿素缩合物。
前述改性三聚氰胺缩合物的制备例如以如下方式进行,首先,按照公知的方法,利用甲醛使三聚氰胺单体羟甲基化且改性、或进一步利用醇使其烷氧基化且改性后,作为由下述通式(16)表示的改性三聚氰胺。另外,作为前述醇,优选低碳醇,例如碳数1~4的醇。
式(16)中,R201可相同也可不同,是含有羟甲基、碳数1~4的烷氧基的烷氧基甲基或氢原子,但至少1个是羟甲基或前述烷氧基甲基。)
作为前述R201,可列举例如羟甲基、甲氧基甲基、乙氧基甲基等烷氧基甲基及氢原子等。作为前述通式(16)的改性三聚氰胺,具体而言可列举三甲氧基甲基单羟甲基三聚氰胺、二甲氧基甲基单羟甲基三聚氰胺、三羟甲基三聚氰胺、环羟甲基三聚氰胺、环甲氧基羟甲基三聚氰胺等。
然后,使用常用方法使通式(16)的改性三聚氰胺或其多聚体(例如二聚体、三聚体等寡聚体)与甲醛进行加成缩合聚合,直至达到所需的分子量为止,获得(C)成分即经甲醛或甲醛-醇改性后的三聚氰胺缩合物。另外,通式(16)的单体及其多聚体的1种以上的改性三聚氰胺缩合物可用作(C)成分。
此外,经甲醛或甲醛-醇改性后的尿素缩合物的制备是例如按照公知的方法利用甲醛使所需的分子量的尿素缩合物羟甲基化而改性,或进一步利用醇使其烷氧基化而改性。
作为前述改性尿素缩合物的具体例,可列举例如甲氧基甲基化尿素缩合物、乙氧基甲基化尿素缩合物、丙氧基甲基化尿素缩合物等。另外,可将这些中的1种以上的改性尿素缩合物用作(C)成分。
另外,作为(C)成分即1分子中平均具有2个以上羟甲基或烷氧基羟甲基的酚化合物,可列举例如(2-羟基-5-甲基)-1,3-苯二甲醇、2,2’,6,6’-四甲氧基甲基双酚A等。
另外,作为(C)成分即1分子中平均具有2个以上环氧基的环氧化合物,可列举例如双酚A型环氧树脂、双酚F型环氧树脂等双酚型环氧树脂、苯酚酚醛清漆型环氧树脂、甲酚清漆型环氧树脂等酚醛清漆型环氧树脂、三酚烷烃型环氧树脂及其聚合物、联苯型环氧树脂、二环戊二烯改性苯酚酚醛清漆型环氧树脂、苯酚芳烷型环氧树脂、联苯芳烷型环氧树脂、含萘环环氧树脂、环氧酯型环氧树脂、脂环式环氧树脂、杂环型环氧树脂等。
这些(C)成分即胺缩合物、酚化合物、环氧化合物可单独使用1种或将2种以上混合使用。
本发明的(C)成分即胺缩合物或酚化合物、环氧化合物相对于前述(A)成分即含硅酮骨架高分子化合物100重量份优选0.5~50重量份,尤其优选1~30重量份。若在0.5重量份以上,则当光照射时可获得充分的固化性,若在50重量份以下,则光固化性树脂组合物中的含硅酮骨架高分子化合物的比例不会下降,所以本发明对于固化物能发挥充分的效果。
[溶剂(D)]
本发明的光固化性树脂组合物可含有溶剂(D)。只要为可溶解前述含硅酮骨架高分子化合物(A)、光致产酸剂(B)、及交联剂(C)、后述的碱性化合物(E)、及其他各种添加剂的溶剂,则可任意选择并调配,但有机溶剂对这些成分的溶解性尤其优良。
作为有机溶剂,可列举例如环己酮、环戊酮、甲基-2-正戊酮等酮类;3-甲氧基丁醇、3-甲基-3-甲氧基丁醇、1-甲氧基-2-丙醇、1-乙氧基-2-丙醇等醇类;丙二醇单甲醚、乙二醇单甲醚、丙二醇单乙醚、乙二醇单乙醚、丙二醇二甲醚、二乙二醇二甲醚等醚类;丙二醇单甲醚乙酸酯、丙二醇单乙醚乙酸酯、乳酸乙酯、丙酮酸乙酯、乙酸丁酯、3-甲氧基丙酸甲酯、3-乙氧基丙酸乙酯、乙酸叔丁酯、丙酸叔丁酯、丙二醇-单-叔丁基醚乙酸酯、γ-丁内酯等酯类等,可单独使用其中的1种或将2种以上组合使用。尤其优选,光致产酸剂的溶解性最佳的乳酸乙酯、环己酮、环戊酮、丙二醇单甲醚乙酸酯、γ-丁内酯及其混合溶剂。
关于前述溶剂的使用量,从光固化性树脂组合物的相容性及粘度的观点出发,相对于含硅酮骨架高分子化合物(A)、光致产酸剂(B)的使用量的合计100重量份,优选50~2000重量份,更优选50~1000重量份,尤其优选50~100重量份。
[碱性化合物(E)]
另外,本发明的光固化性树脂组合物可含有碱性化合物(E)。作为碱性化合物(E),适宜为能抑制光致产酸剂所产生的酸在光固化性树脂层内扩散时的扩散速度的化合物。此外,通过调配前述碱性化合物,能提升解析度,抑制曝光后的灵敏度变化,减小基板依赖性或环境依赖性,提升曝光裕度或图案形状。
作为前述碱性化合物,可列举伯、仲、叔的脂肪族胺类、混合胺类、芳香族胺类、杂环胺类、具有羧基的含氮化合物、具有磺酰基的含氮化合物、具有羟基的含氮化合物、具有羟苯基的含氮化合物、醇性含氮化合物、酰胺衍生物、酰亚胺衍生物等。
具体而言,作为脂肪族伯胺类,可列举氨、甲胺、乙胺、正丙胺、异丙基胺、正丁胺、异丁胺、仲丁胺、叔丁胺、戊胺、叔戊胺、环戊胺、己胺、环己胺、庚胺、辛胺、壬胺、癸胺、十二烷胺、十六烷胺、甲撑二胺、乙二胺、四亚乙基五胺等。
作为脂肪族仲胺类,可列举二甲胺、二乙胺、二正丙胺、二异丙胺、二正丁胺、二异丁胺、二仲丁胺、二戊胺、二环戊胺、二己胺、二环己胺、二庚胺、二辛胺、二壬胺、二癸胺、双十二烷胺、双十六烷胺、N,N-二甲基甲撑二胺、N,N-二甲基乙二胺、N,N-二甲基四亚乙基五胺等。
作为脂肪族叔胺类,可列举三甲胺、三乙胺、三正丙胺、三异丙胺、三正丁胺、三异丁胺、三仲丁胺、三戊胺、三环戊胺、三己胺、三环己胺、三庚胺、三辛胺、三壬胺、三癸胺、三十二烷胺、三十六烷胺、N,N,N’,N’-四甲基甲撑二胺、N,N,N’,N’-四甲基乙二胺、N,N,N’,N’-四甲基四亚乙基五胺等。
此外,作为混合胺类,可列举例如二甲基乙胺、甲基乙基丙胺、苄胺、苯乙胺、苄基二甲胺等。
作为芳香族胺类及杂环胺类的具体例,可列举苯胺衍生物(例如,苯胺、N-甲基苯胺、N-乙基苯胺、N-丙基苯胺、N,N-二甲基苯胺、2-甲基苯胺、3-甲基苯胺、4-甲基苯胺、乙基苯胺、丙基苯胺、三甲基苯胺、2-硝基苯胺、3-硝基苯胺、4-硝基苯胺、2,4-二硝基苯胺、2,6-二硝基苯胺、3,5-二硝基苯胺、N,N-二甲基甲苯胺等)、(对甲苯基)二苯胺、甲基二苯胺、三苯胺、苯二胺、萘胺、萘二胺、吡咯衍生物(例如,吡咯、2H-吡咯、1-甲基吡咯、2,4-二甲基吡咯、2,5-二甲基吡咯、N-甲基吡咯等)、噁唑衍生物(例如,噁唑、异噁唑等)、噻唑衍生物(例如,噻唑、异噻唑等)、咪唑衍生物(例如,咪唑、4-甲基咪唑、4-甲基-2-苯基咪唑等)、吡唑衍生物、呋咱衍生物、吡咯啉衍生物(例如,吡咯啉、2-甲基-1-吡咯啉等)、吡咯烷衍生物(例如,吡咯烷、N-甲基吡咯烷、吡咯烷酮、N-甲基吡咯烷酮等)、咪唑啉衍生物、咪唑烷衍生物、吡啶衍生物(例如,吡啶、甲基吡啶、乙基吡啶、丙基吡啶、丁基吡啶、4-(1-丁基戊基)吡啶、二甲基吡啶、三甲基吡啶、三乙基吡啶、苯基吡啶、3-甲基-2-苯基吡啶、4-叔丁基吡啶、二苯基吡啶、苄基吡啶、甲氧基吡啶、丁氧基吡啶、二甲氧基吡啶、1-甲基-2-吡啶酮、4-吡咯烷基吡啶、1-甲基-4-苯基吡啶、2-(1-乙基丙基)吡啶、氨基吡啶、二甲基氨基吡啶等)、哒嗪衍生物、嘧啶衍生物、吡嗪衍生物、吡唑啉衍生物、吡唑烷衍生物、哌啶衍生物、哌嗪衍生物、吗啉衍生物、吲哚衍生物、异吲哚衍生物、1H-吲唑衍生物、吲哚啉衍生物、喹啉衍生物(例如,喹啉、3-氰基喹啉等)、异喹啉衍生物、噌啉衍生物、喹唑啉衍生物、喹喔啉衍生物、酞嗪衍生物、嘌呤衍生物、蝶啶衍生物、咔唑衍生物、菲啶衍生物、吖啶衍生物、吩嗪衍生物、1,10-菲咯啉衍生物、腺嘌呤衍生物、腺苷衍生物、鸟嘌呤衍生物、鸟苷衍生物、尿嘧啶衍生物、尿苷衍生物等。
另外,作为具有羧基的含氮化合物,可列举例如氨基苯甲酸、吲哚羧酸、氨基酸衍生物(例如烟酸、丙氨酸、精氨酸、天冬氨酸、谷氨酸、甘氨酸、组氨酸、异亮氨酸、甘氨酰亮氨酸、亮氨酸、蛋氨酸、苯丙氨酸、苏氨酸、赖氨酸、3-氨基吡嗪-2-羧酸、甲氧基丙氨酸)等。
作为具有磺酰基的含氮化合物,可例示出3-吡啶磺酸、对甲苯磺酸吡啶鎓等。
作为具有羟基的含氮化合物、具有羟苯基的含氮化合物、醇性含氮化合物,可列举2-羟基吡啶、氨基甲酚、2-喹啉二醇、3-吲哚甲醇水合物、单乙醇胺、二乙醇胺、三乙醇胺、N-乙基二乙醇胺、N,N-二乙基乙醇胺、三异丙醇胺、2,2’-亚氨基二乙醇、2-氨基乙醇、3-氨基-1-丙醇、4-氨基-1-丁醇、4-(2-羟乙基)吗啉、2-(2-羟乙基)吡啶、1-(2-羟乙基)哌嗪、1-[2-(2-羟基乙氧基)乙基]哌嗪、哌啶乙醇、1-(2-羟乙基)吡咯烷、1-(2-羟乙基)-2-吡咯烷酮、3-哌啶基-1,2-丙二醇、3-吡咯烷基-1,2-丙二醇、8-羟基久洛尼定、3-奎宁醇、3-托品醇、1-甲基-2-吡咯烷乙醇、1-氮丙啶乙醇、N-(2-羟乙基)酞酰亚胺、N-(2-羟乙基)异烟酰胺等。
作为酰胺衍生物,可列举甲酰胺、N-甲基甲酰胺、N,N-二甲基甲酰胺、乙酰胺、N-甲基乙酰胺、N,N-二甲基乙酰胺、丙酰胺、苯酰胺等。
作为酰亚胺衍生物,可列举酞酰亚胺、丁二酰亚胺、马来酰亚胺等。
另外,还可添加选自由下述通式(17)表示的碱性化合物中的1种或2种以上。
N(α)w(β)3-w(17)
前述通式(17)中,w为1、2或3。侧链α可相同也可不同,是由下述通式(18)~(20)表示的任一种取代基。侧链β表示相同或不同的、氢原子或直链状、支链状或环状的碳数1~20的烷基,也可含有醚键或羟基。此外,α彼此也可键合而形成环。
这里,前述式中,R300、R302、R305是碳数1~4的直链状或支链状的亚烷基,R301、R304是氢原子、或碳数1~20的直链状、支链状或环状的烷基,且可包含一个或多个羟基、醚键、酯键、内酯环。R303是单键、或碳数1~4的直链状或支链状的亚烷基,R306是碳数1~20的直链状、支链状或环状的烷基,且可包含一个或多个羟基、醚键、酯键、及内酯环。
具体而言,由前述通式(17)表示的化合物可如下例示。可列举三[2-(甲氧基甲氧基)乙基]胺、三[2-(2-甲氧基乙氧基)乙基]胺、三[2-(2-甲氧基乙氧基甲氧基)乙基]胺、三[2-(1-甲氧基乙氧基)乙基]胺、三[2-(1-乙氧基乙氧基)乙基]胺、三[2-(1-乙氧基丙氧基)乙基]胺、三[2-{2-(2-羟基乙氧基)乙氧基}乙基]胺、4,7,13,16,21,24-六氧-1,10-二氮杂双环[8.8.8]二十六烷、4,7,13,18-四氧-1,10-二氮杂双环[8.5.5]二十烷、1,4,10,13-四氧-7,16-二氮杂双环十八烷、1-氮杂-12-冠-4、1-氮杂-15-冠-5、1-氮杂-18-冠-6、三(2-甲酰基氧基乙基)胺、三(2-乙酰氧基乙基)胺、三(2-丙酰氧基乙基)胺、三(2-丁酰氧基乙基)胺、三(2-异丁酰氧基乙基)胺、三(2-戊酰氧基乙基)胺、三(2-新戊酰氧基乙基)胺、N,N-双(2-乙酰氧基乙基)2-(乙酰氧基乙酰氧基)乙胺、三(2-甲氧基羰基氧基乙基)胺、三(2-叔丁氧基羰基氧基乙基)胺、三[2-(2-氧代丙氧基)乙基]胺、三[2-(甲氧基羰基甲基)氧基乙基]胺、三[2-(叔丁氧基羰基甲基氧基)乙基]胺、三[2-(环己基氧基羰基甲基氧基)乙基]胺、三(2-甲氧基羰基乙基)胺、三(2-乙氧基羰基乙基)胺、N,N-双(2-羟乙基)2-(甲氧基羰基)乙胺、N,N-双(2-乙酰氧基乙基)2-(甲氧基羰基)乙胺、N,N-双(2-羟乙基)2-(乙氧基羰基)乙胺、N,N-双(2-乙酰氧基乙基)2-(乙氧基羰基)乙胺、N,N-双(2-羟乙基)2-(2-甲氧基乙氧基羰基)乙胺、N,N-双(2-乙酰氧基乙基)2-(2-甲氧基乙氧基羰基)乙胺、N,N-双(2-羟乙基)2-(2-羟基乙氧基羰基)乙胺、N,N-双(2-乙酰氧基乙基)2-(2-乙酰氧基乙氧基羰基)乙胺、N,N-双(2-羟乙基)2-[(甲氧基羰基)甲氧基羰基]乙胺、N,N-双(2-乙酰氧基乙基)2-[(甲氧基羰基)甲氧基羰基]乙胺、N,N-双(2-羟乙基)2-(2-氧代丙氧基羰基)乙胺、N,N-双(2-乙酰氧基乙基)2-(2-氧代丙氧基羰基)乙胺、N,N-双(2-羟乙基)2-(四氢糠基氧基羰基)乙胺、N,N-双(2-乙酰氧基乙基)2-(四氢糠基氧基羰基)乙胺、N,N-双(2-羟乙基)2-[(2-氧代四氢呋喃-3-基)氧基羰基]乙胺、N,N-双(2-乙酰氧基乙基)2-[(2-氧代四氢呋喃-3-基)氧基羰基]乙胺、N,N-双(2-羟乙基)2-(4-羟基丁氧基羰基)乙胺、N,N-双(2-甲酰基氧基乙基)2-(4-甲酰基氧基丁氧基羰基)乙胺、N,N-双(2-甲酰基氧基乙基)2-(2-甲酰基氧基乙氧基羰基)乙胺、N,N-双(2-甲氧基乙基)2-(甲氧基羰基)乙胺、N-(2-羟乙基)双[2-(甲氧基羰基)乙基]胺、N-(2-乙酰氧基乙基)双[2-(甲氧基羰基)乙基]胺、N-(2-羟乙基)双[2-(乙氧基羰基)乙基]胺、N-(2-乙酰氧基乙基)双[2-(乙氧基羰基)乙基]胺、N-(3-羟基-1-丙基)双[2-(甲氧基羰基)乙基]胺、N-(3-乙酰氧基-1-丙基)双[2-(甲氧基羰基)乙基]胺、N-(2-甲氧基乙基)双[2-(甲氧基羰基)乙基]胺、N-丁基双[2-(甲氧基羰基)乙基]胺、N-丁基双[2-(2-甲氧基乙氧基羰基)乙基]胺、N-甲基双(2-乙酰氧基乙基)胺、N-乙基双(2-乙酰氧基乙基)胺、N-甲基双(2-新戊酰氧基乙基)胺、N-乙基双[2-(甲氧基羰基氧基)乙基]胺、N-乙基双[2-(叔丁氧基羰基氧基)乙基]胺、三(甲氧基羰基甲基)胺、三(乙氧基羰基甲基)胺、N-丁基双(甲氧基羰基甲基)胺、N-己基双(甲氧基羰基甲基)胺、β-(二乙基氨基)-δ-戊内酯,但并不限于此。
另外,前述碱性化合物可单独使用1种或将2种以上组合使用,关于其调配量,从灵敏度的观点出发,相对于(A)成分即含硅酮骨架高分子化合物100重量份优选0~3重量份,尤其优选0.01~1重量份。
[其他添加剂]
本发明的光固化性树脂组合物中除了上文所述的各成分以外,还可以调配添加剂。作为添加剂,可添加例如为了提升涂布性而惯用的表面活性剂。
作为前述表面活性剂,优选为非离子性的表面活性剂,可列举例如氟系表面活性剂,具体而言为全氟烷基聚氧乙烯乙醇、氟化烷基酯、全氟烷基氧化胺、含氟有机硅氧烷系化合物等。这些表面活性剂可使用市售的类型,可列举例如Fluorad“FC-430”(住友3M(株)制)、Surflon“S-141”及“S-145”(都是ASAHI GLASS(株)制)、Unidyne“DS-401”、“DS-4031”及“DS-451”(都是大金工业(株)制)、Megafac“F-8151”(大油墨工业(株)制)、“X-70-093”(信越化学工业(株)制)等。其中优选Fluorad“FC-430”(住友3M(株)制)及“X-70-093”(信越化学工业(株)制)。
此外,作为其他添加剂,还可添加硅烷耦合剂。通过含有硅烷耦合剂,能进一步提高树脂组合物对于被粘合体的密接性。作为硅烷耦合剂,可列举环氧硅烷耦合剂、含芳香族氨基硅烷耦合剂等。它们可单独使用,也可将2种以上组合使用。硅烷耦合剂的含量并无特别限定,当调配时,优选本发明的光固化性树脂组合物的总重量的0.01重量%以上5重量%以下。
本发明的光固化性树脂组合物的制备可利用通常的方法进行。搅拌混合前述各成分,之后根据需要对固体成分利用过滤器等进行过滤,从而能制备本发明的光固化性树脂组合物。
如上所述制备的本发明的光固化性树脂组合物适宜用作例如半导体元件的保护膜、配线的保护膜、覆盖膜、焊料掩模、贯通电极用绝缘膜(TSV用)的材料、以及三维积层中积层基板间的粘合剂。
<光固化性树脂组合物的图案形成方法>
接着,对于使用前述本发明的光固化性树脂组合物的本发明的图案形成方法进行说明。本发明的图案形成方法包含下述步骤。
(i)将本发明的光固化性树脂组合物涂布在基板上,从而在前述基板上形成光固化性树脂层;
(ii)隔着光掩模对前述光固化性树脂层进行曝光;以及,
(iii)进行曝光后的加热处理后,利用显影液进行显影而溶解除去非曝光部,从而形成图案。
此外,还可包含步骤(iv)以100~250℃的温度,对于根据显影而形成图案的皮膜进行后固化。经过这些步骤后,可获得最终所要的电性/电子零件保护用等的皮膜。
在光固化性树脂组合物的图案形成中,首先(i)将光固化性树脂组合物涂布在基板上,形成光固化性树脂层。作为前述基板,可列举例如硅晶片、贯通电极用硅晶片、通过背面研磨而薄膜化的硅晶片、塑料或陶瓷基板、利用离子溅镀法或镀敷法等使基板整面或基板的一部分具有Ni、Au等金属的基板等。也可使用具有开口宽度为10~100μm且深度为10~120μm的槽和孔中的任一者或两者的基板。
作为涂布方法,可采用公知的光刻技术。可利用例如浸渍法、旋涂法、辊涂法等方法涂布。涂布量可根据目的适当选择,可采用形成膜厚成为0.1~200μm、优选1~150μm的光固化性树脂层的涂布量。为了提升基板面的膜厚均匀性,也可在涂布光固化性树脂组合物前向基板滴下溶剂(预湿法)。滴下的溶剂与量可根据目的适当选择,优选用作溶剂的有机溶剂系、例如异丙基醇(IPA)等醇类或环己酮等酮类、以及丙二醇单甲醚等二醇等,但也可使用用于光固化性树脂组合物的溶剂。
这里,为了高效进行光固化反应,也可根据需要通过预加热(预烘烤:PB)使溶剂等预先挥发。预加热可例如以40~140℃进行1分钟~1小时左右。
然后,(ii)隔着光掩模对光固化性树脂层进行曝光。作为曝光波长,一般而言为1~600nm,优选10~600nm,尤其优选190~500nm。该情况下,光掩模也可为例如挖通所需的图案而类型。另外,光掩模的材质并无特别限定,优选遮蔽前述波长的光的材质,适宜使用例如铬等,但并不限于此。作为前述波长的光,可列举例如由射线产生装置产生的各种波长的光,例如g射线、h射线、i射线等紫外线光、远紫外线光(248nm、193nm)等,优选波长248~436nm。曝光量优选10~10000mJ/cm2。
另外,为了提高显影灵敏度,进行曝光后加热处理(PEB(post-exposurebaking))。曝光后的加热处理优选以40~150℃进行0.5~10分钟。通过这样进行加热处理,使曝光部分交联而形成不溶于作为显影液的下述溶剂的不溶图案。
前述曝光后的加热处理后,(iii)利用显影液进行显影,溶解除去非曝光部,从而形成图案。作为显影液,优选用作溶剂的有机溶剂系、例如异丙基醇(IPA)等醇类或环己酮等酮类、以及丙二醇单甲醚等二醇等,但也可使用用于光固化性树脂组合物的溶剂。前述显影方法是通常的方法,可列举例如将形成图案后的基板浸渍于前述显影液的方法等。之后,根据需要进行洗净、冲洗、干燥等,获得具有所需图案的光固化性树脂组合物的皮膜。
另外,本发明的光固化性树脂组合物是用于将2个基板接合的基板粘合剂,也可作为如下粘合剂使用,该粘合剂在热及压力的合适条件下,以在2个基板间形成粘合性结合的方式,使由本发明的组合物形成有皮膜的基板与第2基板接合。形成有皮膜的基板及第2基板中的任一者或两者有时利用切割加工等而芯片化。作为接合条件,加热温度优选50~200℃、1~60分钟。作为接合装置,可使用晶片接合装置一面施加负载一面减压地将晶片彼此贴附、或使用倒装芯片接合装置进行芯片-晶片或芯片-芯片接合。形成在基板间的粘合层可通过后述的后固化处理而提高结合力,形成永久接合。
然后,(iv)对于形成有图案的基板、及图案形成后经过接合的基板,使用烘箱或加热板,以温度100~250℃、尤其优选150~220℃进行后固化。这样,根据本发明的光固化性树脂组合物,即便是200℃附近的相对低温的后固化,也能获得各种膜特性优良的固化物层。另外,若后固化温度为100~250℃,则能提高光固化性树脂组合物的交联密度,除去残存的挥发成分,且从对于基板的密接力、耐热性或强度、电特性、以及接合强度的观点出发更优选。经过贴附(接合)的基板会通过前述后固化处理而增加树脂皮膜的交联密度,且能提高基板粘合力。另外,本发明的交联反应中,不会伴随除气而产生副反应,所以,尤其在用作基板粘合剂的情况下,不会引起贴合缺陷(空隙)。后固化时间可为10分钟~10小时,尤其可为10分钟~3小时。利用本发明的光固化性树脂组合物所得的后固化后的皮膜(固化皮膜)的膜厚通常为1~200μm,优选5~50μm。
然而,当无需形成图案时,例如想要形成单纯的均匀的皮膜时,在前述的图案形成方法的(ii)中,可通过采用不隔着前述光掩模而以适当波长的光进行曝光的步骤来形成皮膜。
<光固化性干膜>
本发明的光固化性干膜的特征在于:是本发明的光固化性树脂组合物涂布在支撑膜上并经过干燥而成。
本发明中的光固化性干膜(支撑膜及光固化性树脂层)为固体,因光固化性树脂层不含溶剂,所以不存在因其挥发而产生的气泡残留在前述光固化性树脂层的内部及具有凹凸的基板之间的情况。若考虑到具有凹凸的基板上的平坦性与阶差被覆性或基板积层间隔,则存在适当膜厚范围。因此,关于前述光固化性树脂层的膜厚,从其平坦性及阶差被覆性、基板积层间隔的观点出发,优选5~200μm,尤其优选10~100μm。
此外,前述光固化性树脂层的粘性率与流动性密切相关联,前述光固化性树脂层在适当粘性率范围内可发挥适当流动性,可进入狭小间隙的深处,或通过使树脂软化能加强与基板的粘合性。因此,关于前述光固化性树脂层的粘性率,从前述光固化性树脂层的流动性的观点出发,在温度80~120℃下可为10~5000Pa·s,优选30~2000Pa·s,尤其优选50~300Pa·s。
本发明的光固化性干膜在密接于具有凹凸的基板(例如,具有开口宽度为10~100μm且深度为10~120μm的槽和孔中的任一者或两者的基板)时,光固化性树脂层会追随前述凹凸而被覆,能实现高平坦性。尤其是,当本发明的光固化性树脂层的主成分为光固化性硅酮组合物时,特征为表面张力低,所以,能实现更高的平坦性。另外,若使前述光固化性树脂层在真空环境下密接于前述基板,则能更有效地防止它们之间产生间隙。
接着,对于本发明中的光固化性干膜的制造方法进行说明。前述光固化性干膜的制造装置可使用一般为了制造粘结剂制品的膜涂布机。作为前述膜涂布机,可列举例如刮刀式涂布机、反向刮刀式涂布机、多功能涂布机、模涂机、模唇涂布机、反向模唇涂布机、直接槽辊(direct gravure)涂布机、转移式槽辊(offset gravure)涂布机、3辊反向底部涂布机、4辊反向底部涂布机等。
将支撑膜从前述膜涂布机的卷出轴卷出,当其经过前述膜涂布机的涂布头时,在前述支撑膜上以规定的厚度涂布光固化性树脂组合物,之后,以规定的温度及规定的时间使其经过热风循环烘箱,且使其在前述支撑膜上干燥而成为光固化性树脂层,从而能获得光固化性干膜。此外,根据需要,使光固化性干膜与从前述膜涂布机的另一卷出轴卷出的保护膜一同在规定的压力下经过层压辊而使前述支撑膜上的前述光固化性树脂层与保护膜贴合后,卷绕在前述膜涂布机的卷绕轴,从而能制造附保护膜的光固化性干膜。该情况下,前述温度优选25~150℃,前述时间优选1~100分钟,前述压力优选0.01~5MPa。
本发明的光固化性干膜中使用的支撑膜可为单层膜也可为多个聚合物膜积层而成的多层膜。作为材质,可为聚乙烯、聚丙烯、聚碳酸酯、聚对苯二甲酸乙二酯等的合成树脂膜,但优选具有合适的可挠性、机械强度及耐热性的聚对苯二甲酸乙二酯。此外,关于这些膜,也可进行如电晕处理或涂布剥离剂等各种处理。这些膜可使用市售品,可列举例如Cerapeel WZ(RX)、Cerapeel BX8(R)(以上为东丽薄膜加工(株)制)、E7302、E7304(以上为东洋纺织(株)制)、Purex G31、Purex G71T1(以上为帝人杜邦薄膜(株)制)、PET38×1-A3、PET38×1-V8、PET38×1-X08(以上为NIPPA(株)制)等。
另一方面,用于保护本发明的光固化性干膜的保护膜可使用与前述支撑膜相同的膜,但优选具有合适可挠性的聚对苯二甲酸乙二酯及聚乙烯。这些膜可使用市售品,作为聚对苯二甲酸乙二酯可列举所有例示的类型,作为聚乙烯,可列举例如GF-8(Tamapoly(株)制)、PE膜0号(NIPPA(株)制)等。
关于前述支撑膜及保护膜的厚度,从光固化性干膜制造的稳定性及对于卷芯的卷度、所谓防止卷缩的观点出发,两者均优选10~100μm,尤其优选25~50μm。
<光固化性干膜的图案形成方法>
光固化性干膜的图案形成包含下述步骤。
(i)使本发明的光固化性干膜密接于基板,从而在前述基板上形成光固化性树脂层;
(ii)隔着光掩模对前述光固化性树脂层进行曝光;以及,
(iii)在进行曝光后的加热处理后,利用显影液进行显影而溶解除去非曝光部,从而形成图案。
另外,优选为进一步包括如下步骤(iv)以100~250℃的温度,对根据显影而形成图案的皮膜进行后固化。
首先,(i)中,在积层有保护膜的情况下,从光固化性干膜剥去保护膜后,使光固化性干膜的光固化性树脂层密接于基板,从而在基板上形成光固化性树脂层。光固化性干膜对于基板的密接可例如使用膜贴附装置进行。
作为前述基板,可列举例如硅晶片、贯通电极用硅晶片、通过背面研磨而薄膜化的硅晶片、塑料或陶瓷基板、利用离子溅镀法或镀敷法等使基板整面或基板的一部分具有Ni、Au等金属的基板等。也可使用具有开口宽度为10~100μm且深度为10~120μm的槽或孔的基板。作为前述膜贴附装置,优选真空层压机。例如,剥离前述光固化性干膜的保护膜,在规定真空度的真空腔室内,使用规定压力的贴附辊,使所露出的前述光固化性树脂层在规定的温度的工作台上密接于前述基板。另外,前述温度优选60~120℃,前述压力优选0~5.0MPa,前述真空度优选50~500Pa。
为了获得所需厚度的光固化性树脂层,可根据需要多次贴附膜。贴附次数在例如1~10次左右时,可获得10~1000μm、尤其是100~500μm厚度左右的光固化性树脂层。
为了高效地进行前述光固化性树脂层的光固化反应、及提升光固化性树脂层与基板的密接性,可根据需要进行预加热(预烘烤)。预烘烤可例如在40~140℃下进行1分钟~1小时左右。贴附于基板的光固化性树脂层与将前述光固化性树脂组合物涂布在基板时同样可进行(ii)曝光、(iii)显影、根据需要进行的基板接合、及(iv)后固化加热处理。另外,光固化性干膜的支撑膜根据工艺可在预烘烤前、或PEB前剥去、或以其他方法除去。
由前述光固化性树脂组合物及光固化性干膜获得的固化皮膜的耐热性、可挠性、电绝缘性、机械特性及与基板等的密接性优良,可良好地用作半导体元件等电性/电子零件保护用皮膜或基板接合用皮膜。
<积层体>
本发明的积层体的特征在于:在具有开口宽度为10~100μm且深度为10~120μm的槽和孔中的任一者或两者的基板上,形成有本发明的光固化性树脂组合物的固化物层、或本发明的光固化性干膜中的光固化性树脂层的固化物层。
作为使用上文所述的本发明的光固化性树脂组合物或光固化性干膜而形成有固化物层的积层体,基板与固化物层的密接性优良,此外,当基板具有此种凹凸时也能具有高平坦性。
[实施例]
以下表示合成例、实施例及比较例而进一步说明本发明,但本发明并不受下述实施例的限制。
下述合成例中,对于各聚合物的重均分子量,使用GPC管TSKgel Super HZM-H(东曹(株)制),以流量0.6毫升/分钟、洗提溶剂四氢呋喃、管柱温度40℃的分析条件,利用以单分散聚苯乙烯为标准的凝胶渗透色谱法(GPC)进行测定。
实施例、比较例中使用的化合物如下所示。
(合成例1)
向具有搅拌机、温度计、氮取代装置及回流冷凝器的3L烧瓶内,加入由前述式(S-1)表示的化合物135.5g(0.25摩尔)、由前述式(S-3a)表示的化合物28.5g(0.05摩尔)、由前述式(S-7)表示的化合物86.0g(0.2摩尔),之后加入甲苯2000g,加热至70℃。之后,加入氯铂酸甲苯溶液(铂浓度0.5重量%)1.0g,且以1小时滴加由前述式(S-5)表示的化合物58.2g(0.30摩尔)及由前述式(S-6)表示的化合物(y=40)604.0g(0.20摩尔)(氢硅烷基的合计摩尔数/烯基的合计摩尔数=1/1、硅酮含有率69.1重量%、S-3a的摩尔数f为1时d=4、c+e=5、g=0)。滴加结束后,加热至100℃且进行6小时熟化后,从反应溶液中减压馏除甲苯,所得生成物的由GPC测定出的聚苯乙烯换算的重均分子量为42000。将所得的树脂作为树脂(1),用于实施例。另外,利用1H NMR(Bruker制),判定所得的树脂为通式(1)的树脂。
(合成例2)
向具有搅拌机、温度计、氮取代装置及回流冷凝器的3L烧瓶内,加入由前述式(S-2)表示的化合物66.3g(0.25摩尔)、由前述式(S-3a)表示的化合物28.5g(0.05摩尔)、由前述式(S-7)表示的化合物86.0g(0.20摩尔)后,添加甲苯2000g,加热至70℃。之后,加入氯铂酸甲苯溶液(铂浓度0.5重量%)1.0g,以1小时滴加由前述式(S-5)表示的化合物58.2g(0.30摩尔)及由前述式(S-6)表示的化合物(y=40)604.0g(0.20摩尔)(氢硅烷基的合计摩尔数/烯基的合计摩尔数=1/1、硅酮含有率71.7重量%、S-3a的摩尔数f为1时d=4、c+e=5、g=0)。滴加结束后,加热至100℃且进行6小时熟化后,从反应溶液中减压馏除甲苯,所得生成物的由GPC测定出的聚苯乙烯换算的重均分子量为45000。将所得的树脂作为树脂(2),用于实施例。另外,利用1H NMR(Bruker制),判定所得的树脂为通式(1)的树脂。
(合成例3)
向具有搅拌机、温度计、氮取代装置及回流冷凝器的3L烧瓶内,加入由前述式(S-2)表示的化合物53.0g(0.20摩尔)、由前述式(S-3a)表示的化合物57.0g(0.10摩尔)、由前述式(S-7)表示的化合物86.0g(0.20摩尔)后,添加甲苯2000g,加热至70℃。之后,加入氯铂酸甲苯溶液(铂浓度0.5重量%)1.0g,以1小时滴加由前述式(S-5)表示的化合物58.2g(0.30摩尔)及由前述式(S-6)表示的化合物(y=40)604.0g(0.20摩尔)(氢硅烷基的合计摩尔数/烯基的合计摩尔数=1/1、硅酮含有率70.4重量%、S-3a的摩尔数f为1时d=2、c+e=2、g=0)。滴加结束后,加热至100℃且进行6小时熟化后,从反应溶液中减压馏除甲苯,所得生成物的由GPC测定出的聚苯乙烯换算的重均分子量为44000。将所得的树脂作为树脂(3),用于实施例。另外,利用1H NMR(Bruker制),判定所得的树脂为通式(1)的树脂。
(合成例4)
向具有搅拌机、温度计、氮取代装置及回流冷凝器的3L烧瓶内,加入由前述式(S-2)表示的化合物26.5g(0.10摩尔)、由前述式(S-3a)表示的化合物57.0g(0.10摩尔)、由前述式(S-4)表示的化合物18.6g(0.10摩尔)、由前述式(S-7)表示的化合物86.0g(0.20摩尔)后,添加甲苯2000g,加热至70℃。之后,加入氯铂酸甲苯溶液(铂浓度0.5重量%)1.0g,以1小时滴加由前述式(S-5)表示的化合物58.2g(0.30摩尔)及由前述式(S-6)表示的化合物(y=20)317g(0.20摩尔)(氢硅烷基的合计摩尔数/烯基的合计摩尔数=1/1、硅酮含有率56.3重量%、S-3a的摩尔数f为1时d=2、c+e=1、g=1)。滴加结束后,加热至100℃且进行6小时熟化后,从反应溶液中减压馏除甲苯,所得生成物的由GPC测定出的聚苯乙烯换算的重均分子量为40000。将所得的树脂作为树脂(4),用于实施例。另外,利用1H NMR(Bruker制),判定所得的树脂为通式(1)的树脂。
(合成例5)
向具有搅拌机、温度计、氮取代装置及回流冷凝器的3L烧瓶内,加入由前述式(S-1)表示的化合物135.5g(0.25摩尔)、由前述式(S-3b)表示的化合物28.5g(0.05摩尔)、由前述式(S-7)表示的化合物86.0g(0.2摩尔)后,添加甲苯2000g,加热至70℃。之后,加入氯铂酸甲苯溶液(铂浓度0.5重量%)1.0g,以1小时滴加由前述式(S-5)表示的化合物58.2g(0.30摩尔)及由前述式(S-6)表示的化合物(y=40)604.0g(0.20摩尔)(氢硅烷基的合计摩尔数/烯基的合计摩尔数=1/1、硅酮含有率69.0重量%、S-3b的摩尔数f为1时d=4、c+e=5、g=0)。滴加结束后,加热至100℃且进行6小时熟化后,从反应溶液中减压馏除甲苯,所得生成物的由GPC测定出的聚苯乙烯换算的重均分子量为43000。将所得的树脂作为树脂(5),用于实施例。另外,利用1H NMR(Bruker制),判定所得的树脂为通式(1)的树脂。
(合成例6)
向具有搅拌机、温度计、氮取代装置及回流冷凝器的3L烧瓶内,加入由前述式(S-2)表示的化合物66.3g(0.25摩尔)、由前述式(S-3b)表示的化合物28.5g(0.05摩尔)、由前述式(S-7)表示的化合物86.0g(0.20摩尔)后,添加甲苯2000g,加热至70℃。之后,加入氯铂酸甲苯溶液(铂浓度0.5重量%)1.0g,以1小时滴加由前述式(S-5)表示的化合物58.2g(0.30摩尔)及由前述式(S-6)表示的化合物(y=40)604.0g(0.20摩尔)(氢硅烷基的合计摩尔数/烯基的合计摩尔数=1/1、硅酮含有率71.7重量%、S-3b的摩尔数f为1时d=4、c+e=5、g=0)。滴加结束后,加热至100℃且进行6小时熟化后,从反应溶液中减压馏除甲苯,所得生成物的由GPC测定出的聚苯乙烯换算的重均分子量为44000。将所得的树脂作为树脂(6),用于实施例。另外,利用1H NMR(Bruker制),判定所得的树脂为通式(1)的树脂。
(合成例7)
向具有搅拌机、温度计、氮取代装置及回流冷凝器的3L烧瓶内,加入由前述式(S-1)表示的化合物108.4g(0.20摩尔)、由前述式(S-2)表示的化合物53.0g(0.20摩尔)、由前述式(S-3a)表示的化合物57.0g(0.10摩尔)后,添加甲苯2000g,加热至70℃。之后,加入氯铂酸甲苯溶液(铂浓度0.5重量%)1.0g,以1小时滴加由前述式(S-5)表示的化合物58.2g(0.30摩尔)及由前述式(S-6)表示的化合物(y=40)604.0g(0.20摩尔)(氢硅烷基的合计摩尔数/烯基的合计摩尔数=1/1、硅酮含有率68.6重量%、S-3a的摩尔数f为1时d=0、c+e=4、g=0)。滴加结束后,加热至100℃且进行6小时熟化后,从反应溶液中减压馏除甲苯,所得生成物的由GPC测定出的聚苯乙烯换算的重均分子量为43000。将所得的树脂作为树脂(7),用于实施例。另外,利用1H NMR(Bruker制),判定所得的树脂为通式(1)的树脂。
(比较合成例1)
向具有搅拌机、温度计、氮取代装置及回流冷凝器的3L烧瓶内,加入由前述式(S-1)表示的化合物135.5g(0.25摩尔)、由前述式(S-4)表示的化合物9.3g(0.05摩尔)、由前述式(S-7)表示的化合物86.0g(0.20摩尔)后,添加甲苯2000g,加热至70℃。之后,加入氯铂酸甲苯溶液(铂浓度0.5重量%)1.0g,以1小时滴加由前述式(S-5)表示的化合物58.2g(0.30摩尔)及由前述式(S-6)表示的化合物(y=40)604.0g(0.20摩尔)(氢硅烷基的合计摩尔数/烯基的合计摩尔数=1/1、硅酮含有率70.6重量%、不含S-3所以S-3摩尔数f=0)。滴加结束后,加热至100℃且进行6小时熟化后,从反应溶液中减压馏除甲苯,所得生成物的由GPC测定出的聚苯乙烯换算的重均分子量为41000。将所得的树脂作为树脂(8),用于比较例。
(比较合成例2)
向具有搅拌机、温度计、氮取代装置及回流冷凝器的3L烧瓶内,加入由前述式(S-2)表示的化合物66.3g(0.25摩尔)、由前述式(S-4)表示的化合物9.3g(0.05摩尔)、由前述式(S-7)表示的化合物86.0g(0.20摩尔)后,添加甲苯2000g,加热至70℃。之后,加入氯铂酸甲苯溶液(铂浓度0.5重量%)1.0g,以1小时滴加由前述式(S-5)表示的化合物58.2g(0.30摩尔)及由前述式(S-6)表示的化合物(y=40)604.0g(0.20摩尔)(氢硅烷基的合计摩尔数/烯基的合计摩尔数=1/1、硅酮含有率73.3重量%、不含S-3所以S-3摩尔数f=0)。滴加结束后,加热至100℃且进行6小时熟化后,从反应溶液中减压馏除甲苯,所得生成物的由GPC测定出的聚苯乙烯换算的重均分子量为46000。将所得的树脂作为树脂(9),用于比较例。
(实施例1~12及比较例1~2)
<光固化性树脂组合物的制备>
按照表1所述的调配量,调配硅酮树脂、光致产酸剂、交联剂、溶剂及碱性化合物,之后在常温下搅拌、混合、溶解后,使用特氟龙(注册商标)制的1.0μm过滤器进行精密过滤,获得实施例1~12及比较例1~2的光固化性树脂组合物。另外,表1中的表示调配量的数值的单位为“重量份”。
[表1]
表1中所记载的光致产酸剂如下所述。
(PAG-1)
表1中所记载的交联剂如下所述。
(CL-1)
(CL-2)
表1中所记载的碱性化合物如下所述。
(AM-1)
<光固化性干膜的作制>
使用模涂机作为膜涂布机、使用聚对苯二甲酸乙二酯膜(厚度38μm)作为支撑膜,将实施例1~12及比较例1~2的光固化性树脂组合物分别涂布在前述支撑膜上。然后,使它们以5分钟经过设定为100℃的热风循环烘箱(长度4m)而进行干燥,从而在支撑膜上形成光固化性树脂层,获得光固化性干膜。从前述光固化性树脂层上方,利用层压辊以压力1MPa贴合作为保护膜的聚乙烯膜(厚度50μm),制作附保护膜的光固化性干膜。各光固化性树脂层的膜厚记载于表2。另外,利用光干渉式厚膜测定仪测定膜厚。
对于实施例1~12及比较例1~2的附保护膜的光固化性干膜,剥离保护膜,使用真空层压机TEAM-100RF(TAKATORI(高鸟)公司制),将真空腔室内的真空度设定为80Pa,使支撑膜上的光固化性树脂层密接于迁移试验用基板(是导电材料为铜、导电部间隔及导电部宽度为20μm、导电部厚度4μm的梳形电极基板)。温度条件为110℃。当恢复常压后,从真空层压机中取出前述基板,剥离支撑膜。接着,为了提高与基板的密接性,利用加热板以130℃进行5分钟预烘烤。为了对于所得的光固化性树脂层形成线与间隔(line and space)图案及接触孔图案,隔着掩模,以405nm的曝光条件使用接触式对准曝光装置进行曝光。光照射后,利用加热板以120℃进行5分钟PEB进行冷却后,利用PGMEA(丙二醇单甲醚乙酸酯)对前述基板进行喷射并进行300秒显影,从而形成图案。
对于按照前述方法形成有图案的基板上的光固化性树脂层,一面使用烘箱以180℃进行2小时氮净化一面进行后固化。之后,利用扫描式电子显微镜(SEM)观察形成的100μm、80μm、60μm、40μm、20μm的接触孔图案截面,以孔贯通至膜底部的最小孔图案作为极限F。进一步根据所得的截面照片评估80μm的接触孔图案的垂直性,垂直图案记为◎,微倒锥形状记为○,倒锥形状记为△,开口不良记为×。
电特性(介电击穿强度):为了评估由光固化性树脂组合物构成的固化皮膜的介电击穿强度,利用棒涂机将实施例1~12及比较例1~2中的各光固化性树脂组合物涂布在13cm×15cm、厚度0.7mm的铁板上,以180℃的烘箱进行2小时加热,获得固化皮膜。光固化性树脂组合物是以固化后的膜厚成为0.2μm的方式涂布。利用该固化皮膜,使用介电击穿测试器TM-5031AM(多摩电测(株)制)测定各个光固化性树脂组合物的固化皮膜的介电击穿强度。
可靠性(密接性、耐开裂性):对于固化后的实施例1~12及比较例1~2的附光固化性树脂膜的晶片,使用具有切割刀片的切割机(DAD685、DISCO公司制、主轴转数为40000rpm、切断速度为20mm/sec),获得10mm×10mm见方的试验片。对所得的试验片(各10片)进行热循环试验(以-25℃下保持10分钟、125℃下保持10分钟的方式反复进行1000次循环),确认热循环试验后的树脂膜相对于晶片的剥离状态、有无裂纹。完全无剥离·裂纹时记为良好,产生哪怕1处剥离时记为剥离,产生哪怕1处裂纹时记为裂纹。
耐热性:对于前述可靠性评估中制作的试验片的试验前重量进行测定,之后,将试验片放置在加热至200℃的烘箱内1000小时,之后,从烘箱中去除试验片,测定试验后重量。当试验前后的重量变化率小于0.5重量%时判定为良好,当试验前后的重量变化率为0.5重量%以上时判定为不良。
针对本发明的实施例及比较例进行的前述固化皮膜及光固化性干膜的特性评估结果示于表2。
[表2]
根据以上结果可知,实施例1~12的组合物几乎没有膜边缘,表现出良好的解析度,作为感光性材料表现出充分的特性,且其固化膜(固化物层)具有绝缘耐压这一电特性或耐热性,此外,热循环试验时的密接性或耐开裂性等特性也优良,对于电路或电子零件的保护膜而言较为有用。从而,能提供可靠性更高的光固化性干膜。
另外,本发明并不限定于前述实施方式。前述实施方式是例示,具有与本发明的权利要求书中记载的技术思想实质性相同的构成且发挥相同作用效果的任一种形态均属于本发明的技术范围。
Claims (17)
1.一种光固化性树脂组合物,其特征在于,含有含硅酮骨架高分子化合物(A)、和在190~500nm的光下会分解而产生酸的光致产酸剂(B),
所述含硅酮骨架高分子化合物(A)由下述式(1)表示,包含硅酮骨架且重均分子量为3000~500000,
式(1)中,R1~R4各自独立地表示碳原子数1~8的一价烃基,m与n各自独立地为0~300的整数,此外,a、b都是正数且a+b=1,X是选自由下述通式(2)、(3)、(4)、(5)及(6)表示的二价基团的群组中的连结基,当将由下述通式(2)表示的单元的摩尔数设为c、将由下述通式(3)表示的单元的摩尔数设为d、将由下述通式(4)表示的单元的摩尔数设为e、将由下述通式(5)表示的单元的摩尔数设为f、将由下述通式(6)表示的单元的摩尔数设为g时,c、d、e、g为0或正数,f为正数,其中,c+d+e为正数;
j和p为0或1,此外,R5和R8表示氢原子或甲基,h和k为0~7的整数,R6、R7、R9及R10各自独立地为碳数1~4的烷基或烷氧基,彼此不同或相同,i和r为0、1、及2中的任一个,
式(4)中,R11表示氢原子或甲基,q为0~7的整数,
式(5)中,Y为二价有机基,R12各自独立地表示氢原子或碳原子数1~8的一价烃基,一部分被卤素原子取代或不被卤素原子取代,彼此不同或相同,R13各自独立地表示碳原子数1~8的亚烷基,彼此不同或相同,此外,Rx是单键或与Rxx闭环而形成环结构的基团,Rxx是氢原子或碳原子数1~8的一价烃基,
式(6)中,t与u各自独立地为0~300的整数,此外,R14表示氢原子或甲基,R15与R16各自独立地表示碳原子数1~8的一价烃基,s为0~7的整数,
并且,前述通式(5)为下述式(5-1),
式(5-1)中,R12及R13与上文所述相同;R17各自独立地表示碳原子数1~8的亚烷基,彼此不同或相同;R18各自独立地表示氢原子或碳原子数1~8的一价烃基,一部分被卤素原子取代或不被卤素原子取代,彼此不同或相同,Y是从下述式中选出的二价有机基团,
2.如权利要求1所述的光固化性树脂组合物,其中,进一步含有交联剂(C)。
3.如权利要求2所述的光固化性树脂组合物,其中,前述交联剂(C)是选自经甲醛或甲醛-醇改性后的胺缩合物、1分子中平均具有2个以上羟甲基或烷氧基羟甲基的酚化合物、及1分子中平均具有2个以上环氧基的环氧化合物中的任一种以上。
4.如权利要求1至3中任一项所述的光固化性树脂组合物,其中,进一步含有溶剂(D)。
5.如权利要求1至3中任一项所述的光固化性树脂组合物,其中,进一步含有碱性化合物(E)。
6.一种光固化性干膜,其特征在于,是权利要求1至3中任一项所述的光固化性树脂组合物涂布在支撑膜上并经过干燥而成。
7.一种积层体,其特征在于,在具有开口宽度为10~100μm且深度为10~120μm的槽和孔中的任一者或两者的基板上,形成有权利要求1至3中任一项所述的光固化性树脂组合物的固化物层。
8.一种积层体,其特征在于,在具有开口宽度为10~100μm且深度为10~120μm的槽和孔中的任一者或两者的基板上,形成有权利要求6所述的光固化性干膜中的光固化性树脂层的固化物层。
9.一种图案形成方法,其特征在于,包括如下步骤:
(i)将权利要求1至3中任一项所述的光固化性树脂组合物涂布在基板上,从而在前述基板上形成光固化性树脂层;
(ii)隔着光掩模对前述光固化性树脂层进行曝光;以及,
(iii)在进行曝光后的加热处理后,利用显影液进行显影而溶解除去非曝光部,从而形成图案。
10.一种图案形成方法,其特征在于,包括如下步骤:
(i)使权利要求6所述的光固化性干膜密接于基板,从而在前述基板上形成光固化性树脂层;
(ii)隔着光掩模对前述光固化性树脂层进行曝光;以及,
(iii)在进行曝光后的加热处理后,利用显影液进行显影而溶解除去非曝光部,从而形成图案。
11.如权利要求9所述的图案形成方法,其特征在于,进一步包括如下步骤:(iv)以100~250℃的温度,对根据显影而形成图案的皮膜进行后固化。
12.如权利要求10所述的图案形成方法,其特征在于,进一步包括如下步骤:(iv)以100~250℃的温度,对根据显影而形成图案的皮膜进行后固化。
13.如权利要求9所述的图案形成方法,其中,前述基板具有开口宽度为10~100μm且深度为10~120μm的槽和孔中的任一者或两者。
14.如权利要求10所述的图案形成方法,其中,前述基板具有开口宽度为10~100μm且深度为10~120μm的槽和孔中的任一者或两者。
15.如权利要求1至3中任一项所述的光固化性树脂组合物,其中,前述光固化性树脂组合物是电性/电子零件保护用皮膜的材料。
16.如权利要求1至3中任一项所述的光固化性树脂组合物,其中,前述光固化性树脂组合物是用于将2个基板接合的基板接合用皮膜的材料。
17.一种含硅酮骨架高分子化合物,其中,由下述式(1)表示,包含硅酮骨架且重均分子量为3000~500000,
式(1)中,R1~R4各自独立地表示碳原子数1~8的一价烃基,m与n各自独立地为0~300的整数,此外,a、b都是正数且a+b=1,X是选自由下述通式(2)、(3)、(4)、(5)及(6)表示的二价基团的群组中的连结基,当将由下述通式(2)表示的单元的摩尔数设为c、将由下述通式(3)表示的单元的摩尔数设为d、将由下述通式(4)表示的单元的摩尔数设为e、将由下述通式(5)表示的单元的摩尔数设为f、将由下述通式(6)表示的单元的摩尔数设为g时,c、d、e、g为0或正数,f为正数,其中,c+d+e为正数,X的摩尔数=c+d+e+f+g,0<c/X的摩尔数≤0.4、0<d/X的摩尔数≤0.7、0<e/X的摩尔数≤0.4、0.1≤f/X的摩尔数≤0.6、0≤g/X的摩尔数≤0.4,
j和p为0或1,此外,R5和R8表示氢原子或甲基,h和k为0~7的整数,R6、R7、R9及R10各自独立地为碳数1~4的烷基或烷氧基,彼此不同或相同,i和r为0、1、及2中的任一个,
式(4)中,R11表示氢原子或甲基,q为0~7的整数,
式(5)中,Y为二价有机基,R12各自独立地表示氢原子或碳原子数1~8的一价烃基,一部分被卤素原子取代或不被卤素原子取代,彼此不同或相同,R13各自独立地表示碳原子数1~8的亚烷基,彼此不同或相同,此外,Rx是单键或与Rxx闭环而形成环结构的基团,Rxx是氢原子或碳原子数1~8的一价烃基,
式(6)中,t与u各自独立地为0~300的整数,此外,R14表示氢原子或甲基,R15与R16各自独立地表示碳原子数1~8的一价烃基,s为0~7的整数,
并且,前述通式(5)为下述式(5-1),
式(5-1)中,R12及R13与上文所述相同;R17各自独立地表示碳原子数1~8的亚烷基,彼此不同或相同;R18各自独立地表示氢原子或碳原子数1~8的一价烃基,一部分被卤素原子取代或不被卤素原子取代,彼此不同或相同,Y是从下述式中选出的二价有机基团,
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Application Number | Priority Date | Filing Date | Title |
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JP2016130447A JP6616743B2 (ja) | 2016-06-30 | 2016-06-30 | シリコーン骨格含有高分子化合物、光硬化性樹脂組成物、光硬化性ドライフィルム、積層体、及びパターン形成方法 |
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EP3263626A1 (en) | 2018-01-03 |
EP3263626B1 (en) | 2024-03-13 |
CN107556480A (zh) | 2018-01-09 |
JP6616743B2 (ja) | 2019-12-04 |
KR102228143B1 (ko) | 2021-03-17 |
TWI806825B (zh) | 2023-07-01 |
TW201819475A (zh) | 2018-06-01 |
US20180004088A1 (en) | 2018-01-04 |
KR20180003410A (ko) | 2018-01-09 |
JP2018002848A (ja) | 2018-01-11 |
US10451970B2 (en) | 2019-10-22 |
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