CN110498926A - 含有硅亚苯基和聚醚结构的聚合物 - Google Patents

含有硅亚苯基和聚醚结构的聚合物 Download PDF

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CN110498926A
CN110498926A CN201910405687.XA CN201910405687A CN110498926A CN 110498926 A CN110498926 A CN 110498926A CN 201910405687 A CN201910405687 A CN 201910405687A CN 110498926 A CN110498926 A CN 110498926A
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丸山仁
加藤英人
菅生道博
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Shin Etsu Chemical Co Ltd
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Abstract

本发明涉及含有硅亚苯基和聚醚结构的聚合物，将在主链中含有硅亚苯基和聚醚结构的新型聚合物用于配制具有改善的可靠性的感光组合物。

Description

含有硅亚苯基和聚醚结构的聚合物
相关申请的交叉引用
本非临时申请根据35 U.S.C.§119(a)要求于2018年5月17日在日本提交的专利申请No.2018-095338的优先权，由此通过引用将其全部内容并入本文。
技术领域
本发明涉及含有硅亚苯基和聚醚结构的聚合物。
背景技术
在现有技术中，用于半导体器件的感光保护膜和用于多层印刷电路板的感光介电膜由感光聚酰亚胺、环氧树脂和有机硅组合物形成。为了保护这样的基板和电路板，已知许多感光材料，专利文献1公开了具有改善的柔性的感光有机硅组合物。
专利文献2公开了基于含有硅亚苯基结构的有机硅聚合物的感光有机硅组合物。尽管该感光有机硅组合物具有改善的对于液体光致抗蚀剂剥离剂的耐化学性，但固化物在热循环试验(-25℃/10分钟保持和125℃/10分钟保持的重复1,000个循环)过程中能够从基板剥离或开裂。希望可靠性的进一步改善。
引文列表
专利文献1：JP-A 2002-088158(USP 6,590,010,EP 1186624)
专利文献2：JP-A 2008-184571(USP 7,785,766,EP 1953183)
发明内容
本发明的目的在于提供新型聚合物，其可用于配制具有改善的可靠性的感光组合物。
本发明人已发现通过含有硅亚苯基结构和聚醚结构的聚合物解决了未解决的问题。
根据本发明，提供在主链中含有硅亚苯基结构和聚醚结构的聚合物。
该聚合物优选具有环氧基和/或酚羟基。
而且优选地，该聚合物具有3,000-500,000的重均分子量。
具体地，该聚合物定义为包含具有下式(1)-(4)的重复单元。
其中X1为具有下式(X1)的二价基团，X2为具有下式(X2)的二价基团，X3为具有下式(X3)的二价基团，X4为具有下式(X4)的二价基团，并且p、q、r和s为下述范围内的数：0<p<1，0≤q<1，0≤r<1，0≤s<1，0<q+r+s<1，和p+q+r+s＝1。
其中R1和R2各自独立地为氢或C1-C8一价烃基，R3和R4各自独立地为氢或甲基，a1和a2各自独立地为1-6的整数，并且n为0-100的整数。
其中Y1为单键、亚甲基、丙烷-2,2-二基、1,1,1,3,3,3-六氟丙烷-2,2-二基或芴-9,9-二基，R11和R12各自独立地为氢或甲基，R13和R14各自独立地为C1-C4烷基或烷氧基，b1和b2各自独立地为0-7的整数，并且c1和c2各自独立地为0-2的整数，
其中Y2为单键、亚甲基、丙烷-2,2-二基、1,1,1,3,3,3-六氟丙烷-2,2-二基或芴-9,9-二基，R21和R22各自独立地为氢或甲基，R23和R24各自独立地为C1-C4烷基或烷氧基，d1和d2各自独立地为0-7的整数，并且e1和e2各自独立地为0-2的整数。
其中R31和R32各自独立地为氢或甲基，并且f1和f2各自独立地为0-7的整数。
在优选的实施方式中，R1和R2各自为氢并且n为5-20的整数。
发明的有利效果
本发明的聚合物可容易地合成并且用于配制具有改善的可靠性的感光组合物。
具体实施方式
本文中使用的表示(Cn-Cm)意指每个基团含有n-m个碳原子的基团。
含有硅亚苯基和聚醚结构的聚合物
本发明提供在主链中含有硅亚苯基结构和聚醚结构的聚合物。该聚合物优选具有环氧基和/或酚羟基。
该聚合物优选包含具有下式(1)-(4)的重复单元，以下有时将它们表示为重复单元(1)-(4)。
式(1)中，X1为具有式(X1)的二价基团。
式(X1)中，R1和R2各自独立地为氢或C1-C8一价烃基，R3和R4各自独立地为氢或甲基，a1和a2各自独立地为1-6、优选1-4、更优选1或2的整数，并且n为0-100、优选1-50、更优选5-20的整数。
C1-C8一价烃基可以为直链、支化或环状，并且包括例如一价脂族烃基例如C1-C8烷基和C2-C8烯基以及一价芳族烃基例如C6-C8芳基和C7或C8芳烷基。
C1-C8烷基的实例包括甲基、乙基、正丙基、异丙基、环丙基、正丁基、异丁基、仲丁基、叔丁基、环丁基、正戊基、环戊基、正己基、环己基、正庚基和正辛基。烯基的实例包括乙烯基、丙烯基、丁烯基和戊烯基。芳基的实例包括苯基、2-甲基苯基、3-甲基苯基、4-甲基苯基、2-乙基苯基、3-乙基苯基、4-乙基苯基和二甲基苯基。芳烷基的实例包括苄基和苯乙基。
R1和R2优选为氢或C1-C8烷基，更优选为氢或甲基。
式(X1)中，带有下标n的氧化烯单元可无规地或交替地排列，或者可包括多个相同的氧化烯单元的嵌段。
式(2)中，X2为具有式(X2)的二价基团。
式(X2)中，Y1为单键、亚甲基、丙烷-2,2-二基、1,1,1,3,3,3-六氟丙烷-2,2-二基或芴-9,9-二基，R11和R12各自独立地为氢或甲基，R13和R14各自独立地为C1-C4烷基或烷氧基，b1和b2各自独立地为0-7的整数，并且c1和c2各自独立地为0-2的整数。
C1-C4烷基可以为直链、支化或环状，并且其实例包括甲基、乙基、正丙基、异丙基、环丙基、正丁基、异丁基、仲丁基、叔丁基和环丁基。C1-C4烷氧基可以为直链、支化或环状，并且其实例包括甲氧基、乙氧基、正丙氧基、异丙氧基、环丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基和环丁氧基。
式(3)中，X3为具有式(X3)的二价基团。
式(X3)中，Y2为单键、亚甲基、丙烷-2,2-二基、1,1,1,3,3,3-六氟丙烷-2,2-二基或芴-9,9-二基，R21和R22各自独立地为氢或甲基，R23和R24各自独立地为C1-C4烷基或烷氧基，d1和d2各自独立地为0-7的整数，并且e1和e2各自独立地为0、1或2的整数。C1-C4烷基或烷氧基的实例如在式(X2)的说明中所例示。
式(4)中，X4为具有式(X4)的二价基团。
式(X4)中，R31和R32各自独立地为氢或甲基，并且f1和f2各自独立地为0-7的整数。
式(1)-(4)中，p、q、r和s分别表示聚合物中的重复单元(1)、(2)、(3)和(4)的含量(摩尔分数)，为下述范围内的数：0<p<1，0≤q<1，0≤r<1，0≤s<1，0<q+r+s<1和p+q+r+s＝1。从膜形成或处理的方面出发，p、q、r和s优选为下述范围内的数：0.1≤p≤0.9，0≤q≤0.9，0≤r≤0.9，0≤s≤0.9和0.1≤q+r+s≤0.9，更优选为0.2≤p≤0.8，0≤q≤0.8，0≤r≤0.8，0≤s≤0.8和0.2≤q+r+s≤0.8，条件是p+q+r+s＝1。重复单元(1)-(4)可无规地或嵌段地排列。
本发明的聚合物优选具有3,000-500,000、更优选5,000-200,000的重均分子量(Mw)。具有该范围内的Mw的聚合物在大多数常用有机溶剂中完全地可溶。应指出地是，在本公开中Mw是使用四氢呋喃作为洗脱剂、相对于聚苯乙烯标样、采用凝胶渗透色谱(GPC)测定的。
该聚合物可由无规地或交替地排列的重复单元(1)-(4)或者各自由相同种类的单元组成的多个嵌段组成。
含有硅亚苯基和聚醚结构的聚合物的制备方法
该聚合物可在金属催化剂的存在下通过以下所示的具有式(5)的化合物、具有式(X1’)的化合物、和选自具有式(X2’)的化合物、具有式(X3’)的化合物和具有式(X4’)的化合物中的至少一种化合物的加成聚合而制备。
其中Y1、Y2、R1-R4、R11-R14、R21-R24、R31、R32、a1、a2、b1、b2、c1、c2、d1、d2、e1、e2、f1、f2和n如上所定义。
本文中使用的金属催化剂的实例包括铂族金属单质例如铂(包括铂黑)、铑和钯；氯化铂、氯铂酸和氯铂酸盐例如H2PtCl4·xH2O、H2PtCl6·xH2O、NaHPtCl6·xH2O、KHPtCl6·xH2O、Na2PtCl6·xH2O、K2PtCl4·xH2O、PtCl4·xH2O、PtCl2和Na2HPtCl4·xH2O，其中x优选为0-6的整数，更优选0或6；USP 3,220,972中记载的醇改性氯铂酸；USP 3,159,601、USP 3,159,662和USP 3,775,452中记载的氯铂酸-烯烃络合物；在氧化铝、二氧化硅和碳的载体上包含铂族金属例如铂黑和铂的负载催化剂；铑-烯烃络合物；氯三(三苯基膦)铑(称为威尔金森催化剂)；和氯化铂、氯铂酸和氯铂酸盐与含有乙烯基的硅氧烷、特别是含有乙烯基的环硅氧烷的络合物。
以催化量使用该催化剂，基于用于聚合反应的反应物的总重量，该催化量优选为0.001-0.1重量％的铂族金属。在聚合反应中，如果需要，可使用溶剂。适合的溶剂为烃溶剂例如甲苯和二甲苯。关于聚合条件，聚合温度优选在40-150℃、更优选60-120℃的范围内选择，以致不会使催化剂失活并且在短时间内完成聚合。聚合时间根据单体的种类和量而变化，为了防止水分进入聚合体系中，优选在约0.5-约100小时、更优选约0.5-约30小时内完成聚合反应。聚合反应的完成后，如果有，则将溶剂馏除，得到所需的聚合物。
对反应程序并无特别限制。优选的程序为：首先将具有式(X1’)的化合物与选自具有式(X2’)的化合物、具有式(X3’)的化合物和具有式(X4’)的化合物中的一种以上的化合物混合，将该混合物加热，将金属催化剂添加到该混合物中，然后历时0.1-5小时滴加具有式(5)的化合物。
优选以如下的量将反应物组合：具有式(5)的化合物上的氢甲硅烷基与具有式(X1’)、(X2’)、(X3’)和(X4’)的化合物上的全部烯基的摩尔比可在0.67/1至1.67/1的范围内，更优选为0.83/1至1.25/1。可使用分子量控制剂例如单烯丙基化合物(例如邻-烯丙基苯酚)、一氢硅烷(例如三乙基氢硅烷)或一氢硅氧烷来控制聚合物的Mw。
实施例
以下通过例示而不是通过限制来给出本发明的实施例。实施例中，在分析条件：流量0.6mL/min、四氢呋喃洗脱剂和柱温度40℃下使用GPC柱TSKGEL Super HZM-H(TosohCorp.)相对于单分散的聚苯乙烯标样采用凝胶渗透色谱(GPC)来测定重均分子量(Mw)。
以下示出聚合物合成中使用的化合物。
实施例1
树脂1的合成
在装备有搅拌器、温度计、氮吹扫管线和回流冷凝器的3-L烧瓶中装入156.8g(0.40mol)的具有式(S-1)的化合物、53.9g(0.10mol)的具有式(S-3a)的化合物(来自NOFCorp.的UNIOX)和2,000g的甲苯并在70℃下加热。然后，添加1.0g的氯铂酸的甲苯溶液(铂浓度0.5wt％)，并且历时1小时滴加97.0g(0.50mol)的具有式(S-5)的化合物。氢甲硅烷基的总摩尔数与烯基的总摩尔数之比为1/1。滴加结束时，将反应溶液在100℃下加热并且熟化6小时。在真空中将甲苯从反应溶液中馏除，得到树脂1。树脂1具有43,000的Mw。采用1H-NMR波谱(Bruker Corp.)，树脂1被确定为含有重复单元(1)和(2)的聚合物。
实施例2
树脂2的合成
在装备有搅拌器、温度计、氮吹扫管线和回流冷凝器的3-L烧瓶中装入172.0g(0.40mol)的具有式(S-7)的化合物、53.9g(0.10mol)的具有式(S-3a)的化合物和2,000g的甲苯并在70℃下加热。然后，添加1.0g的氯铂酸的甲苯溶液(铂浓度0.5wt％)，并且历时1小时滴加97.0g(0.50mol)的具有式(S-5)的化合物。氢甲硅烷基的总摩尔数与烯基的总摩尔数之比为1/1。滴加结束时，将反应溶液在100℃下加热并且熟化6小时。在真空中将甲苯从反应溶液中馏除，得到树脂2。树脂2具有25,000的Mw。采用1H-NMR波谱(Bruker Corp.)，树脂2被确定为含有重复单元(1)和(3)的聚合物。
实施例3
树脂3的合成
在装备有搅拌器、温度计、氮吹扫管线和回流冷凝器的3-L烧瓶中装入106.0g(0.40mol)的具有式(S-2)的化合物、53.9g(0.10mol)的具有式(S-3a)的化合物和2,000g的甲苯并在70℃下加热。然后，添加1.0g的氯铂酸的甲苯溶液(铂浓度0.5wt％)，并且历时1小时滴加97.0g(0.50mol)的具有式(S-5)的化合物。氢甲硅烷基的总摩尔数与烯基的总摩尔数之比为1/1。滴加结束时，将反应溶液在100℃下加热并且熟化6小时。在真空中将甲苯从反应溶液中馏除，得到树脂3。树脂3具有34,000的Mw。采用1H-NMR波谱(Bruker Corp.)，树脂3被确定为含有重复单元(1)和(4)的聚合物。
实施例4
树脂4的合成
在装备有搅拌器、温度计、氮吹扫管线和回流冷凝器的3-L烧瓶中装入9.8g(0.025mol)的具有式(S-1)的化合物、10.8g(0.025mol)的具有式(S-7)的化合物、13.3g(0.05mol)的具有式(S-2)的化合物、215.6g(0.40mol)的具有式(S-3a)的化合物和2,000g的甲苯并在70℃下加热。然后，添加1.0g的氯铂酸的甲苯溶液(铂浓度0.5wt％)，并且历时1小时滴加97.0g(0.50mol)的具有式(S-5)的化合物。氢甲硅烷基的总摩尔数与烯基的总摩尔数之比为1/1。滴加结束时，将反应溶液在100℃下加热并且熟化6小时。在真空中将甲苯从反应溶液中馏除，得到树脂4。树脂4具有50,000的Mw。采用1H-NMR波谱(BrukerCorp.)，树脂4被确定为含有重复单元(1)、(2)、(3)和(4)的聚合物。
实施例5
树脂5的合成
在装备有搅拌器、温度计、氮吹扫管线和回流冷凝器的3-L烧瓶中装入9.8g(0.025mol)的具有式(S-1)的化合物、10.8g(0.025mol)的具有式(S-7)的化合物、13.3g(0.05mol)的具有式(S-2)的化合物、327.2g(0.40mol)的具有式(S-3b)的化合物和2,000g的甲苯并在70℃下加热。然后，添加1.0g的氯铂酸的甲苯溶液(铂浓度0.5wt％)，并且历时1小时滴加97.0g(0.50mol)的具有式(S-5)的化合物。氢甲硅烷基的总摩尔数与烯基的总摩尔数之比为1/1。滴加结束时，将反应溶液在100℃下加热并且熟化6小时。在真空中将甲苯从反应溶液中馏除，得到树脂5。树脂5具有58,000的Mw。采用1H-NMR波谱(BrukerCorp.)，树脂5被确定为含有重复单元(1)、(2)、(3)和(4)的聚合物。
以上合成了树脂1-5，证实了提供在主链中含有硅亚苯基结构和聚醚结构的新型聚合物。
通过引用将日本专利申请No.2018-095338并入本文。
尽管已对一些优选的实施方式进行了说明，但在上述教导下可对其进行多种变形和改变。因此应理解，在没有脱离所附权利要求的范围的情况下，本发明可在具体说明以外来实施。

Claims (6)

1.聚合物，其在主链中含有硅亚苯基结构和聚醚结构。
2.根据权利要求1所述的聚合物，其具有环氧基和/或酚羟基。
3.根据权利要求1所述的聚合物，其具有3,000-500,000的重均分子量。
4.根据权利要求1所述的聚合物，其包含具有下式(1)-(4)的重复单元：
其中X1为具有下式(X1)的二价基团，X2为具有下式(X2)的二价基团，X3为具有下式(X3)的二价基团，X4为具有下式(X4)的二价基团，并且p、q、r和s为下述范围内的数：0<p<1，0≤q<1，0≤r<1，0≤s<1，0<q+r+s<1，和p+q+r+s＝1，
其中R1和R2各自独立地为氢或C1-C8一价烃基，R3和R4各自独立地为氢或甲基，a1和a2各自独立地为1-6的整数，并且n为0-100的整数，
其中Y1为单键、亚甲基、丙烷-2,2-二基、1,1,1,3,3,3-六氟丙烷-2,2-二基或芴-9,9-二基，R11和R12各自独立地为氢或甲基，R13和R14各自独立地为C1-C4烷基或烷氧基，b1和b2各自独立地为0-7的整数，并且c1和c2各自独立地为0-2的整数，
其中Y2为单键、亚甲基、丙烷-2,2-二基、1,1,1,3,3,3-六氟丙烷-2,2-二基或芴-9,9-二基，R21和R22各自独立地为氢或甲基，R23和R24各自独立地为C1-C4烷基或烷氧基，d1和d2各自独立地为0-7的整数，并且e1和e2各自独立地为0-2的整数，
其中R31和R32各自独立地为氢或甲基，并且f1和f2各自独立地为0-7的整数。
5.根据权利要求4所述的聚合物，其中R1和R2各自为氢。
6.根据权利要求4所述的聚合物，其中n为5-20的整数。
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