TWI796481B - 含有矽伸苯基骨架及聚醚骨架的聚合物 - Google Patents

含有矽伸苯基骨架及聚醚骨架的聚合物 Download PDF

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TWI796481B
TWI796481B TW108116886A TW108116886A TWI796481B TW I796481 B TWI796481 B TW I796481B TW 108116886 A TW108116886 A TW 108116886A TW 108116886 A TW108116886 A TW 108116886A TW I796481 B TWI796481 B TW I796481B
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丸山仁
加藤英人
菅生道博
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日商信越化學工業股份有限公司
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Abstract

本發明係關於提供一種可賦予提高信賴性的感光性組成物之新穎聚合物。其為於主鏈含有矽伸苯基骨架及聚醚骨架的聚合物。

Description

含有矽伸苯基骨架及聚醚骨架的聚合物
本發明係關於含有矽伸苯基骨架及聚醚骨架的聚合物。
過去作為具有感光性的半導體元件保護膜或多層印刷基板用絶緣膜，利用感光性聚醯亞胺組成物或感光性環氧樹脂組成物、感光性聚矽氧組成物等。作為使用於如此基板、迴路保護用的感光性材料，此等中已有文獻提出可撓性特優的感光性聚矽氧組成物(專利文獻1)。
又，已有提出將含有矽伸苯基骨架的聚矽氧型高分子化合物作為主成分之感光性聚矽氧組成物(專利文獻2)。然而，前述感光性聚矽氧組成物雖對於光阻剝離液等藥品耐性有提高，但有著於加熱循環試驗(在-25℃保持10分鐘，在125℃保持10分鐘，重複1,000次循環)時自基板會剝離硬化物，或於硬化物會有裂紋等問題，可望信賴性可進一步提高。 [先前技術文獻] [專利文獻]
[專利文獻1] 特開2002-88158號公報 [專利文獻2] 特開2008-184571號公報
[發明所解決的問題]
本發明為有鑑於前述事情所成者，以提供賦予更提高信賴性之感光性組成物的新穎聚合物為目的。 [解決課題的手段]
本發明者們，欲達成前述目的而重複詳細檢討結果，發現藉由含有矽伸苯基骨架及聚醚骨架的聚合物可解決前述課題而完成本發明。
即，本發明提供下述含有矽伸苯基骨架及聚醚骨架的聚合物。 1.於主鏈含有矽伸苯基骨架及聚醚骨架的聚合物。 2.具有環氧基及/或酚性羥基的1之聚合物。 3.重量平均分子量為3,000～500,000的1或2之聚合物。 4.含有下述式(1)～(4)所示重複單位者之1～3中任1的聚合物。
Figure 02_image001
[式中，X1 為下述式(X1)所示2價基。X2 為下述式(X2)所示2價基。X3 為下述式(X3)所示2價基。X4 為下述式(X4)所示2價基。p、q、r及s為滿足0＜p＜1、0≦q＜1、0≦r＜1、0≦s＜1、0＜q+r+s＜1，及p+q+r+s=1的數。
Figure 02_image003
(式中，R1 及R2 各獨立為氫原子或碳數1～8的1價烴基。R3 及R4 各獨立為氫原子或甲基。a1 及a2 各獨立為1～6的整數。n為0～100的整數)。
Figure 02_image005
(式中，Y1 為單鍵、伸甲基、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 及R12 各獨立為氫原子或甲基。R13 及R14 各獨立為碳數1～4的烷基或烷氧基。b1 及b2 各獨立為0～7的整數。c1 及c2 各獨立為0～2的整數)。
Figure 02_image007
(式中，Y2 為單鍵、伸甲基、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 及R22 各獨立為氫原子或甲基。R23 及R24 各獨立為碳數1～4的烷基或烷氧基。d1 及d2 各獨立為0～7的整數。e1 及e2 各獨立為0～2的整數)。
Figure 02_image009
(式中，R31 及R32 各獨立為氫原子或甲基。f1 及f2 各獨立為0～7的整數)]。 5.R1 及R2 皆為氫原子的4之聚合物。 6.n為5～20的整數之4或5的聚合物。 [發明之效果]
本發明之聚合物容易合成且可得到賦予信賴高的感光性組成物。
[實施發明的型態] [含有矽伸苯基骨架及聚醚骨架的聚合物]
本發明之聚合物為於主鏈含有矽伸苯基骨架及聚醚骨架者。前述聚合物以具有環氧基及/或酚性羥基者為佳。
作為如此聚合物，以含有下述式(1)～(4)所示重複單位(以下各稱為重複單位1～4)者為佳。
Figure 02_image011
式(1)中，X1 為下述式(X1)所示2價基。
Figure 02_image013
式(X1)中，R1 及R2 各獨立為氫原子或碳數1～8的1價烴基。R3 及R4 各獨立為氫原子或甲基。a1 及a2 各獨立為1～6的整數，以1～4的整數為佳，以1或2為較佳。n為0～100的整數，以1～50的整數為佳，以5～20的整數為較佳。
前述碳數1～8的1價烴基可為直鏈狀、支鏈狀、環狀中任一種，作為該具體例子，可舉出碳數1～8的烷基、碳數2～8的烯基等1價脂肪族烴基、碳數6～8的芳基、碳數7或8的芳烷基等1價芳香族烴基。
作為前述碳數1～8的烷基，可舉出甲基、乙基、n-丙基、異丙基、環丙基、n-丁基、異丁基、sec-丁基、tert-丁基、環丁基、n-戊基、環戊基、n-己基、環己基、n-庚基、n-辛基等。作為前述烯基，可舉出乙烯基、丙烯基、丁烯基、戊烯基等。
作為前述芳基，可舉出苯基、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、二甲基苯基等。作為前述芳烷基，可舉出苯甲基、苯乙基等。
作為R1 及R2 ，以氫原子或碳數1～8的烷基為佳，以氫原子或甲基為較佳。
式(X1)中，下標n所示環氧化物單位，可為無規鍵結者，亦可為交互鍵結者，獲益可為含有複數個同種環氧化物單位之嵌段者。
式(2)中，X2 為下述式(X2)所示2價基。
Figure 02_image015
式(X2)中，Y1 為單鍵、伸甲基、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 及R12 各獨立為氫原子或甲基。R13 及R14 各獨立為碳數1～4的烷基或烷氧基。b1 及b2 各獨立為0～7的整數。c1 及c2 各獨立為0～2的整數。
前述碳數1～4的烷基可為直鏈狀、支鏈狀、環狀中任一種，作為該具體例子，可舉出甲基、乙基、n-丙基、異丙基、環丙基、n-丁基、異丁基、sec-丁基、tert-丁基、環丁基等。
前述碳數1～4的烷氧基可為直鏈狀、支鏈狀、環狀中任一種，作為該具體例子，可舉出甲氧基、乙氧基、n-丙基氧基、異丙基氧基、環丙基氧基、n-丁基氧基、異丁基氧基、sec-丁基氧基、tert-丁基氧基、環丁基氧基等。
式(3)中，X3 為下述式(X3)所示2價基。
Figure 02_image017
式(X3)中，Y2 為單鍵、伸甲基、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 及R22 各獨立為氫原子或甲基。R23 及R24 各獨立為碳數1～4的烷基或烷氧基。d1 及d2 各獨立為0～7的整數。e1 及e2 各獨立為0、1或2。作為前述碳數1～4的烷基或烷氧基，可舉出與式(X2)的說明中所述的相同者。
式(4)中，X4 為下述式(X4)所示2價基。
Figure 02_image019
式(X4)中，R31 及R32 各獨立為氫原子或甲基。f1 及f2 各獨立為0～7的整數。
式(1)～(4)中，p、q、r及s可表示聚合物中之重複單位1、2、3及4的含有率(莫耳分率)，滿足0＜p＜1、0≦q＜1、0≦r＜1、0≦s＜1、0＜q+r+s＜1及p+q+r+s =1的數。p、q、r及s由成膜性或處理性之觀點來看，以0.1≦p≦0.9、0≦q≦0.9、0≦r≦0.9、0≦s≦0.9、0.1≦q+r+s≦0.9為佳，較佳為0.2≦p≦0.8、0≦q≦0.8、0≦r≦0.8、0≦s≦0.8、0.2≦q+r+s≦0.8。但，p+q+r+s=1。且重複單位1～4可為無規方式，亦可為嵌段方式的以鍵結形成方式所鍵結者。
本發明之聚合物的重量平均分子量(Mw)以3,000～500,000為佳，以5,000～200,000為較佳。Mw若在前述範圍，可確保對於泛用有機溶劑的充分溶解性。且，對於本發明，Mw為藉由將四氫呋喃作為溶離溶劑使用的凝膠滲透層析法(GPC)之聚苯乙烯換算測定値。
本發明之聚合物可為重複單位1～4以無規方式鍵結者，亦可為以交互方式鍵結者，或亦可為含有複數個各單位之嵌段者。
[含有矽伸苯基骨架及聚醚骨架的聚合物之製造方法] 前述聚合物可係由，將選自由下述式(5)所示化合物及下述式(X1')所示化合物，以及下述式(X2')所示化合物、下述式(X3')所示化合物及下述式(X4')所示化合物的至少1種化合物，在金屬觸媒存在下使其進行加成聚合而製造。
Figure 02_image021
Figure 02_image023
(式中，Y1 、Y2 、R1 ～R4 、R11 ～R14 、R21 ～R24 、R31 、R32 、a1 、a2 、b1 、b2 、c1 、c2 、d1 、d2 、e1 、e2 、f1 、f2 及n與前述相同)。
作為前述金屬觸媒，可使用鉑(含有鉑黑)、銠、鈀等鉑族金屬單體；H2 PtCl4 •xH2 O、H2 PtCl6 •xH2 O、NaHPtCl6 •xH2 O、KHPtCl6 •xH2 O、Na2 PtCl6 •xH2 O、K2 PtCl4 •xH2 O、PtCl4 •xH2 O、PtCl2 、Na2 HPtCl4 •xH2 O(其中，x以0～6的整數為佳，特佳為0或6)等氯化鉑、氯化鉑酸及氯化鉑酸鹽；醇變性氯化鉑酸(例如，美國專利第3,220,972號說明書所記載者)；氯化鉑酸與烯烴之錯體(例如美國專利第3,159,601號說明書、美國專利第3,159,662號說明書及美國專利第3,775,452號說明書所記載者)；將鉑黑或鈀等鉑族金屬於氧化鋁、二氧化矽、碳等載體上載持者；銠-烯烴錯體；氯參(三苯基膦)銠(所謂威爾金森觸媒)；氯化鉑、氯化鉑酸或氯化鉑酸鹽與含有乙烯基的矽氧烷(特別為含有乙烯基的環狀矽氧烷)的錯體等。
觸媒的使用量為觸媒量，通常作為鉑族金屬對於反應聚合物的總量而言為0.001～0.1質量%者為佳。對於前述聚合反應，勢必要可使用溶劑。作為溶劑，例如以甲苯、二甲苯等烴系溶劑為佳。作為前述聚合條件，由觸媒不會失去活性，且在短時間可完成聚合的觀點來看，聚合溫度例如40～150℃，特別以60～120℃為佳。聚合時間雖依聚合物的種類及量而相異，但欲防止於聚合系統中濕氣的介入，約0.5～100小時，特別以0.5～30小時結束者為佳。如此結束聚合反應後，使用溶劑時，可藉由蒸餾此而得到前述聚合物。
反應方法並無特別限定，首先混合選自式(X1')所示化合物、式(X2')所示化合物、式(X3')所示化合物及式(X4')所示化合物的至少1種或2種以上，經加熱後於前述混合溶液中加入金屬觸媒，其次將式(5)所示化合物經0.1～5小時滴入者為佳。
各原料化合物對於式(X1')所示化合物、式(X2')所示化合物、式(X3')所示化合物及式(X4')所示化合物所具有的烯基之合計而言，式(5)所示化合物所具有的氫矽基在莫耳比係以調配成0.67～1.67為佳，較佳為0.83～1.25。本發明之聚合物的Mw可藉由將如o-烯丙基酚的單烯丙基化合物，或如三乙基氫矽烷的單氫矽烷或單氫矽氧烷作為分子量調整劑使用而可控制。 [實施例]
以下，表示實施例及比較例而進一步說明本發明，但本發明並未限定於下述實施例。且，對於下述實施例，Mw為使用作為GPC管柱的TSKGEL Super HZM-H(Tosoh公司(股)製)，以流量0.6mL/分，溶離溶劑四氫呋喃，管柱溫度40℃之分析條件下，藉由將單分散聚苯乙烯作為標準的凝膠滲透層析法(GPC)而測定。
使用於聚合物的合成之化合物如以下所示。
Figure 108116886-A0305-02-0015-1
[實施例1]樹脂1之合成
於具備攪拌機、溫度計、氮取代裝置及迴流冷卻器之3L燒瓶中，加入式(S-1)所示化合物156.8g(0.40莫耳)及式(S-3a)所示化合物(日油(股)製UNIOX)53.9g(0.10莫耳)後，加入甲苯2,000g，於70℃進行加熱。其後，投入氯化鉑酸 甲苯溶液(鉑濃度0.5質量%)1.0g，將式(S-5)所示化合物97.0g(0.50莫耳)經1小時滴入(氫矽基之合計莫耳數/烯基之合計莫耳數=1/1)。滴下終了後，加熱至100℃後進行6小時熟成後，自反應溶液將甲苯減壓餾去，得到樹脂1。樹脂1之Mw為43,000。且，樹脂1為藉由1H-NMR(Bluker公司製)確認為含有重複單位1及2之聚合物。
[實施例2]樹脂2之合成
於具備攪拌機、溫度計、氮取代裝置及迴流冷卻器之3L燒瓶中，加入式(S-7)所示化合物172.0g(0.40莫耳)及式(S-3a)所示化合物53.9g(0.10莫耳)後，加入甲苯2,000g，於70℃進行加熱。其後投入氯化鉑酸甲苯溶液(鉑濃度0.5質量%)1.0g，將式(S-5)所示化合物97.0g(0.50莫耳)經1小時滴入(氫矽基之合計莫耳數/烯基之合計莫耳數=1/1)。滴入終了後，加熱至100℃並進行6小時熟成後，自反應溶液將甲苯進行減壓餾去，得到樹脂2。樹脂2之Mw為25,000。且，樹脂2藉由1H-NMR(Bluker公司製)確認為含有重複單位1及3之聚合物。
[實施例3]樹脂3之合成
於具備攪拌機、溫度計、氮取代裝置及迴流冷卻器之3L燒瓶中，加入式(S-2)所示化合物106.0g(0.40莫耳)及式(S-3a)所示化合物53.9g(0.10莫耳)後，加入甲苯2,000g並於70℃進行加熱。其後，投入氯化鉑酸甲苯溶液(鉑濃度0.5質量%)1.0g，將式(S-5)所示化合物97.0g(0.50莫耳)經1小時滴入(氫矽基之合計莫耳數/烯基之合計莫耳數=1/1)。滴入終了後，加熱至100℃並進行6小時熟成後，自反應溶液將甲苯進行減壓餾去，得到樹脂3。樹脂3的Mw為34,000。且樹脂3藉由1 H-NMR(Bluker公司製)確認為含有重複單位1及4之聚合物。
[實施例4] 樹脂4之合成 於具備攪拌機、溫度計、氮取代裝置及迴流冷卻器之3L燒瓶中，加入式(S-1)所示化合物9.8g(0.025莫耳)、式(S-7)所示化合物10.8g(0.025莫耳)、式(S-2)所示化合物13.3g(0.05莫耳)及式(S-3a)所示化合物215.6g(0.40莫耳)後，加入甲苯2,000g，於70℃進行加熱。其後投入氯化鉑酸甲苯溶液(鉑濃度0.5質量%)1.0g，將式(S-5)所示化合物97.0g(0.50莫耳)經1小時滴入(氫矽基之合計莫耳數/烯基之合計莫耳數=1/1)。滴下終了後，加熱至100℃並進行6小時熟成後，自反應溶液將甲苯進行減壓餾去，得到樹脂4。樹脂4的Mw為50,000。且樹脂4藉由1 H-NMR(Bluker公司製)確認為含有重複單位1、2、3及4之聚合物。
[實施例5] 樹脂5之合成 於具備攪拌機、溫度計、氮取代裝置及迴流冷卻器之3L燒瓶中，加入式(S-1)所示化合物9.8g(0.025莫耳)及式(S-7)所示化合物10.8g(0.025莫耳)、式(S-2)所示化合物13.3g(0.05莫耳)、式(S-3b)所示化合物327.2g(0.40莫耳)後，加入甲苯2,000g，於70℃進行加熱。其後投入氯化鉑酸甲苯溶液(鉑濃度0.5質量%)1.0g，將式(S-5)所示化合物97.0g(0.50莫耳)經1小時滴入(氫矽基之合計莫耳數/烯基之合計莫耳數=1/1)。滴入終了後，加熱至100℃並進行6小時熟成後，自反應溶液將甲苯進行減壓餾去，得到樹脂5。樹脂5的Mw為58,000。且樹脂5藉由1 H-NMR(Bluker公司製)確認其為含有重複單位1、2、3及4之聚合物。
由以上結果可得知，依據本發明可提供並可合成含有如樹脂1～5之於主鏈含有矽伸苯基骨架及聚醚骨架的新穎聚合物。

Claims (5)

  1. 一種聚合物，其特徵為於主鏈含有矽伸苯基骨架及聚醚骨架，且具有環氧基及/或酚性羥基的聚合物，含有下述式(1)~(4)所示重複單位者；
    Figure 108116886-A0305-02-0019-2
     [式中，X1為下述式(X1)所示2價基；X2為下述式(X2)所示2價基；X3為下述式(X3)所示2價基；X4為下述式(X4)所示2價基；p、q、r及s為滿足0<p<1、0≦q<1、0≦r<1、0≦s<1、0<q+r+s<1及p+q+r+s=1的數；
    Figure 108116886-A0305-02-0019-3
     (式中，R1及R2各獨立為氫原子或碳數1~8的1價烴基；R3及R4各獨立為氫原子或甲基；a1及a2各獨立為1~6的整數；n為1~100的整數)
    Figure 108116886-A0305-02-0020-4
     (式中，Y1為單鍵、伸甲基、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及R12各獨立為氫原子或甲基；R13及R14各獨立為碳數1~4的烷基或烷氧基；b1及b2各獨立為0~7的整數；c1及c2各獨立為0~2的整數)；
    Figure 108116886-A0305-02-0020-5
     (式中，Y2為單鍵、伸甲基、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及R22各獨立為氫原子或甲基；R23及R24各獨立為碳數1~4的烷基或烷氧基；d1及d2各獨立為0~7的整數；e1及e2各獨立為0~2的整數)；
    Figure 108116886-A0305-02-0020-6
     (式中，R31及R32各獨立為氫原子或甲基；f1及f2各獨立為0~7的整數)]。
  2. 如請求項1之聚合物，其中重量平均分子量為3,000~500,000。
  3. 如請求項1或2之聚合物，其中R1及R2皆為氫原子。
  4. 如請求項3之聚合物，其中n為1~50的整數。
  5. 如請求項4之聚合物，其中n為5~20的整數。
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