TW201816055A - 感光性接著劑組成物 - Google Patents
感光性接著劑組成物 Download PDFInfo
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- TW201816055A TW201816055A TW106129435A TW106129435A TW201816055A TW 201816055 A TW201816055 A TW 201816055A TW 106129435 A TW106129435 A TW 106129435A TW 106129435 A TW106129435 A TW 106129435A TW 201816055 A TW201816055 A TW 201816055A
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Abstract
本發明之課題為提供新穎之感光性接著劑組成物。 解決方法為,含有下述(A)成分、(B)成分、(C)成分及(D)成分,又就質量比,比較前述(A)成分含有更多前述(B)成分的感光性接著劑組成物。 (A)成分:具有下述式(1)所表示之結構單位,末端具有下述式(2)所表示之結構的聚合物,(B)成分:具有前述式(1)所表示之結構單位,末端具有前述羧基或羥基的聚合物,(C)成分:自由基型光聚合引發劑,及(D)成分:溶劑(該等式中,X表示碳原子數1至6之烷基、乙烷基、烯丙基及縮水甘油基,m及n表示各自獨立之0或1,Q表示碳原子數1至16之二價羥基,Z表示碳原子數1至4之二價連結基,該二價連結基係與前述式(1)之-O-基鍵結,R1
表示氫原子或甲基)。
Description
[0001] 本發明係有關含有導入可自由基交聯之部位的聚合物之感光性接著劑組成物。
[0002] 近年來伴隨著行動電話、IC卡等之電子機器的高機能化及小型化,而要求半導體裝置高積體化。有關其方法曾檢討使半導體元件本身微細化,半導體元件之間以縱方向堆積的堆疊結構。製作堆疊結構時,接合半導體元件之間係使用接著劑。但已知之作為接著劑用的丙烯酸樹脂、環氧樹脂及聚矽氧樹脂之耐熱性僅為250℃程度,而有無法使用於金屬唧筒之電極接合、離子擴散步驟等要求250℃以上之高溫般步驟的問題。 [0003] 專利文獻1曾揭示,使用於光半導體用接著劑的含有三聚異氰酸基環之聚合物,及含有其之組成物。又記載該含有三聚異氰酸基環之聚合物係藉由,鹼金屬化合物存在下使N-單取代三聚異氰酸與二鹵化物進行反應,或使N,N,’N’’-三取代三聚異氰酸與矽烷化合物進行矽氫加成反應所得。另外記載前述組成物作為光半導體用接著劑時,係以50℃~250℃之烤箱加熱30分鐘至4小時之方法進行接著。 [0004] 另外,代表液晶顯示器(LCD)、有機EL(OLED)顯示器所代表之薄型顯示器(FPD)市場急速擴充下。液晶顯示器中作為顯示面板之基材雖為玻璃基板,但針對降低更薄型化、輕量化、可撓性化、卷對卷(Roll-to-Roll)步驟的加工成本,曾開發使用塑料基板之可撓性顯示器。但已知之作為塑料基板所使用的樹脂材料用之PET樹脂、PEN樹脂、PC樹脂之耐熱性僅為250℃程度,而有無法使用於先前薄膜電晶體(TFT)形成步驟所要求的250℃以上高溫之步驟的問題。 [0005] 又,專利文獻2曾揭示製造可見光之透光率較高且具有優良耐熱性及耐溶劑性之硬化膜的組成物。該文獻也曾揭示前述組成物可作為接著劑用。 [先前技術文獻] [專利文獻] [0006] 專利文獻1:日本特開2008-143954號公報 專利文獻2:國際公開第2013/035787號報告
[發明所欲解決之課題] [0007] 專利文獻2所記載之組成物不為感光性之樹脂組成物。因此由專利文獻2所記載之組成物所形成的膜,無法藉由微影步驟形成具有所希望之形狀的圖型。故需求能同時符合可由微影步驟製圖,及接著時無需高溫下之加熱步驟般該等要件的接著組成物。 [解決課題之方法] [0008] 為了解決上述課題經本發明者們專心檢討後發現,藉由使構成組成物之聚合物為,具有特定末端結構之聚合物,及末端具有取代該特定末端結構用之羧基或羥基的聚合物,又就質量比,比較前者聚合物含有更多後者聚合物,可於無需上述溫度下之加熱步驟,而得備有所希望之接著力的該組成物。 [0009] 即,本發明之第一態樣為含有下述(A)成分、(B)成分、(C)成分及(D)成分,又就質量比,比較前述(A)成分含有更多前述(B)成分的感光性接著劑組成物。 (A)成分:具有下述式(1)所表示之結構單位,末端具有下述式(2)所表示之結構的聚合物 (B)成分:具有前述式(1)所表示之結構單位,末端具有羧或羥基的聚合物 (C)成分:自由基型光聚合引發劑 (D)成分:溶劑(該等式中,X表示碳原子數1至6之烷基、乙烯基、烯丙基或縮水甘油基,m及n表示各自獨立之0或1,Q表示碳原子數1至16之二價烴基,Z表示碳原子數1至4之二價連結基,該二價連結基係與前述式(1)之-O-基鍵結,R1
表示氫原子或甲基)。 [0010] 前述式(1)中Q所表示之二價烴基如,表示直鏈狀或支鏈狀之伸烷基、含有以雙鍵鍵結之2個碳原子的基,或主鏈含有可具有至少1個取代基之脂環式烴基或芳香族烴基的基。 [0011] 前述式(2)中Z所表示之二價連結基如,表示可具有至少1個作為取代基用之烴基的直鏈狀或支鏈狀之伸烷基。 [0012] 前述(A)成分與前述(B)成分之質量比較佳為1:2至1:20。 [0013] 前述感光性接著劑組成物可另含有二官能(甲基)丙烯酸酯及/或多官能硫醇。 [0014] 本發明之第二態樣為,具有將本發明之第一態樣的感光性接著劑組成物塗佈於第一基板上的步驟、以50℃至160℃之溫度將塗佈於前述第一基板上之感光性接著劑組成物預熱的步驟,使前述預熱後之形成於前述第一基板上的塗膜曝光的步驟,使前述曝光後之前述塗膜顯像的步驟,及於前述顯像後將第二基板貼附於前述第一基板後加熱使前述塗膜熱硬化的步驟之接著方法。 [發明之效果] [0015] 本發明之感光性接著劑組成物為,以特定質量比含有作為末端導入可自由基交聯之部位的聚合物用之具有特定末端結構的聚合物,及具有取代該特定末端結構用之羧基或羥基的聚合物,具另含有自由基型光聚合引發劑,因此無需250℃或以上之溫度下的加熱步驟,可形成具有優良耐溶劑性之硬化膜。由本發明之感光性接著劑組成物所形成之硬化膜防透濕性亦優異。進而,本發明之感光性接著劑組成物具有較高之接著力,故適用為半導體元件用、MEMS(Micro Electro Mechanical Systems)用,NEMS(Nano Electro Mechanical Systems)用,有機EL顯示器及圖像傳感器用之接著劑。
<(A)成分> [0016] 本發明之感光性接著劑組成物為,含有作為(A)成分用之具有前述式(1)所表示之結構單位,末端具有前述式(2)所表示之結構的聚合物,該聚合物之重量平均分子量藉由後述凝膠滲透色譜(以下本說明書簡稱為GPC)分析所得的標準聚苯乙烯換算值例如為1,000至50,000,較佳為1,000至20,000。 [0017] 前述式(1)中X所表示的碳原子數1至6之烷基如,甲基、乙基、n-丙基、i-丙基、n-丁基、i-丁基、s-丁基、t-丁基、n-戊基、1-甲基-n-丁基、2-甲基-n-丁基、3-甲基-n-丁基、1,1-二甲基-n-丙基、1,2-二甲基-n-丙基、2,2-二甲基-n-丙基、1-乙基-n-丙基、n-己基、1-甲基-n-戊基、2-甲基-n-戊基、3-甲基-n-戊基、4-甲基-n-戊基、1,1-二甲基-n-丁基、1,2-二甲基-n-丁基、1,3-二甲基-n-丁基、2,2-二甲基-n-丁基、2,3-二甲基-n-丁基、3,3-二甲基-n-丁基、1-乙基-n-丁基、2-乙基-n-丁基、1,1,2-三甲基-n-丙基、1,2,2-三甲基-n-丙基、1-乙基-1-甲基-n-丙基、1-乙基-2-甲基-n-丙基等。 [0018] 前述式(1)中Q所表示的碳原子數1至16之二價烴基如,主鏈含有直鏈狀或支鏈狀之伸烷基、含有以雙鍵鍵結2個碳原子之基,或可具有至少1個取代基之脂環式烴基或芳香族烴基的基。該類基如下述式(a)至式(m)所表示之基。[0019] 前述式(2)中Z所表示的碳原子數1至4之二價連結基如,表示可具有至少1個作為取代基用之羥基的直鏈狀或支鏈狀之伸烷基。Z表示該類伸烷基時,前述式(2)所表示之末端結構如下述式(2-1)及式(2-2)所表示之結構。[0020] 前述(A)成分之聚合物例如係經由下述過程合成。使具有三嗪三酮結構之環氧化合物,與具有2個羧基或羥基之化合物反應,得前述式(1)所表示之結構單位,及末端具有羧基或羥基之聚合物中間物。其次使具有前述末端之聚合物中間物與具有環氧基之(甲基)丙烯酸酯反應。 <(B)成分> [0021] 本發明之感光性接著劑組成物為,含有作為(B)成分用的具有前述式(1)所表示之結構單位,及末端具有羧基或羥基之聚合物。該聚合物之重量平均分子量藉由後述GPC分析所得的標準聚苯乙烯換算值例如為1,000至50,000,較佳為1,000至20,000,更佳為1,000至10,000。 [0022] 前述(B)成分之聚合物例如係經由下述過程合成。使具有三嗪三酮結構之環氧化合物,與具有2個羧基或羥基之化合物反應,得具有前述式(1)所示之結構單位,及末端具有羧基或羥基之聚合物。 <(C)成分> [0023] 本發明之感光性接著劑組成物為,含有作為(C)成分用之自由基型光聚合引發劑。該光聚合引發劑可為相對於光硬化時所使用之光源的波長域具有吸收力之化合物,無特別限定,例如tert-丁基過氧-iso-丁酸酯、2,5-二甲基-2,5-雙(苯醯二氧基)己烷、1,4-雙[α-(tert-丁基二氧基)-iso-丙氧基]苯、二-tert-丁基過氧化物、2,5-二甲基-2,5-雙(tert-丁基二氧基)己烯氫過氧化物、α-(iso-丙基苯基)-iso-丙基氫過氧化物、tert-丁基氫過氧化物、1,1-雙(tert-丁基二氧基)-3,3,5-三甲基環己烷、丁基-4,4-雙(tert-丁基二氧基)戊酸酯;環己酮過氧化物、2,2’5,5’-四(tert-丁基過氧基羰基)二苯甲酮、3,3’,4,4’-四(tert-丁基過氧基羰基)二苯甲酮、3,3’,4,4’-四(tert-戊基過氧基羰基)二苯甲酮、3,3’,4,4’-四(tert-己氧基羰基)二苯甲酮、3,3’-雙(tert-丁基過氧基羰基)-4,4’-二羧基二苯甲酮、tert-丁基過氧基苯甲酸酯、二-tert-丁基二過氧基間苯二甲酸酯等之有機過氧化物;9,10-蒽醌、1-氯蒽醌、2-氯蒽醌、八甲基蒽醌、1,2-苯并蒽醌等之醌類;苯偶因甲酯、苯偶因乙基醚、α-甲基苯偶因、α-苯基苯偶因等之苯偶因衍生物;2,2-二甲氧基-1,2-二苯基乙烷-1-酮、1-羥基-環己基-苯基-酮、2-羥基-2-甲基-1-苯基-丙烷-1-酮、1-[4-(2-羥基乙氧基)-苯基]-2-羥基-2-甲基-1-丙烷-1-酮、2-羥基-1-[4-{4-(2-羥基-2-甲基-丙醯基)苄基}-苯基]-2-甲基-丙烷-1-酮、苯基乙醛酸甲基酯、2-甲基-1-[4-(甲基硫基)苯基]-2-嗎啉基丙烷-1-酮、2-苄基-2-二甲基胺基-1-(4-嗎啉基苯基)-1-丁酮、2-二甲基胺基-2-(4-甲基-苄基)-1-(4-嗎啉-4-基-苯基)-丁烷-1-酮等之烷基苯酮系化合物;雙(2,4,6-三甲基苯醯基)-苯基膦氧化物、2,4,6-三甲基苯醯基-二苯基-膦氧化物等之醯基膦氧化物系化合物;2-(o-苯醯基肟)-1-[4-(苯基硫基)苯基]-1,2-辛二酮、1-(o-乙醯基肟)-1-[9-乙基-6-(2-甲基苯醯基)-9H-咔唑-3-基]乙酮等之肟酯系化合物。 [0024] 上述自由基型光聚合引發劑可由市售品取得,例如IRGACURE[註冊商標]651、184、2959、127、907、369、379EG、819、819DW、1800、1870、784、OXE01、OXE02、250、1173、MBF、TPO、4265、TPO(以上為BASF公司製)、KAYACURE[註冊商標]DETX、MBP、DMBI、EPA、OA(以上為日本化藥(股)製)、VICURE-10、55(以上為STAUFFER Co. LTD製)、ESACURE KIP150、TZT、1001、KTO46、KB1、KL200、KS300、EB3、三嗪-PMS、三嗪A、三嗪B(以上為日本DKSH(股)製)。ADEKA OPTOMER-N-1717、N-1414、N-1606(以上為ADEKA(股)製)。該等自由基型光聚合引發劑可單獨使用,或二種以上組合使用。 [0025] 本發明之感光性接著劑組成物中自由基型光聚合引發劑之含量,相對於上述(A)成分及(B)成分之聚合物總含量例如為0.01phr至30phr,較佳為0.1phr至15phr。該含量之比例未達下限值時,將無法得到充分之硬化性。此時phr係表示相對於聚合物之質量100g的自由基型光聚合引發劑之質量。 <(D)成分> [0026] 本發明之感光性接著劑組成物為含有溶劑。該溶劑可為半導體裝置製造過程中可使用之有機溶劑,無特別限定,例如環己酮、甲基異戊基酮、2-丁酮、2-庚酮等之酮類;乙二醇、乙二醇單乙酸酯、二乙二醇、二乙二醇單乙酸酯、丙二醇、丙二醇單乙酸酯、二丙二醇或二丙二醇單乙酸酯、及該等之單甲基醚、單乙基醚、單丙基醚、單丁基醚、單苯基醚等之多價醇及其衍生物;二噁烷等之環式醚類;γ-丁內酯等之內酯類;及乳酸甲酯、乳酸乙酯、乙酸甲酯、乙酸乙酯、乙酸丁酯、丙酮酸甲酯、丙酮酸乙酯、甲氧基丙酸甲酯、乙氧基丙酸乙酯、2-羥基異丁酸甲酯等之酯類。該等有機溶劑可單獨使用,或二種以上混合使用。以由本發明之感光性接著劑組成物去除溶劑後之成分為固體成分時,該感光性接著劑組成物中固體成分所佔有之比例,例如為1質量%至80質量%。 <交聯性化合物> [0027] 本發明之感光性接著劑組成物於必要時可含有作為交聯性化合物用之二官能(甲基)丙烯酸酯。該二官能(甲基)丙烯酸酯係指,分子兩端具有丙烯醯基或甲基丙烯醯基之化合物。該化合物如,三環癸烷二甲醇二丙烯酸酯、三環癸烷二甲醇二甲基丙烯酸酯、三環癸烷二乙醇二丙烯酸酯、及三環癸烷二乙醇二甲基丙烯酸酯。 [0028] 上述二官能(甲基)丙烯酸酯可由市售品取得,例如A-DCP、DCP(以上為新中村化學工業(股)製)。該等化合物可單獨使用,或二種以上組合使用。 [0029] 本發明之感光性接著劑組成物中二官能(甲基)丙烯酸酯之含量,相對於上述(A)成分及(B)成分聚合物之總含量例如為5質量%至50質量%,較佳為10質量%至30質量%。 [0030] 本發明之感光性接著劑組成物於必要時可含有作為交聯性化合物用之多官能硫醇。該多官能硫醇係指,分子之末端具有複數(例如2個,3個或4個)硫醇基之化合物。該化合物如,季戊四醇四(3-巰基丁酸酯)、1,4-雙(3-巰基丁醯氧基)丁烷、1,3,5-三(3-巰基丁醯氧基乙基)-1,3,5-三嗪-2,4,6(1H,3H,5H)三酮、三羥甲基丙烷三(3-巰基丁酸酯),及三羥甲基乙烷三(3-巰基丁酸酯)。 [0031] 上述多官能硫醇可由市售品取得,例如karenz MT[註冊商標]PE1、BD1、NR1(以上為昭和電工(股)製)。該等化合物可單獨使用,或二種以上組合使用。 [0032] 本發明之感光性接著劑組成物中多官能硫醇之含量,相對於上述(A)成分及(B)成分之聚合物的總含量例如為0.1質量%至15質量%,較佳為0.5質量%至10質量%。 <其他添加劑> [0033] 本發明之感光性接著劑組成物於必要時可另含有環氧化合物、光酸發生劑、熱酸發生劑、無機填料、表面活性劑等之添加劑。 [0034] 本發明之感光性接著劑組成物含有環氧化合物時,該環氧化合物如,1,4-丁二醇二縮水甘油醚、1,2-環氧-4-(環氧乙基)環己烷、甘油三縮水甘油醚、二乙二醇二縮水甘油醚、2,6-二縮水甘油基苯基縮水甘油醚、1,1,3-三[p-(2,3-環氧丙氧基)苯基]丙烷、1,2-環己烷二羧酸二縮水甘油酯、4,4’-伸甲基雙(N,N-二縮水甘油基苯胺)、3,4-環氧環己基甲基-3,4-環氧環己烷羧酸酯、三羥甲基乙烷三縮水甘油醚、三縮水甘油基-p-胺基苯酚、四縮水甘油基間二甲苯二胺、四縮水甘油基二胺基二苯基甲烷、四縮水甘油基-1,3-雙胺基甲基環己烷、雙酚A-二縮水甘油醚、雙酚S-二縮水甘油醚、季戊四醇四縮水甘油醚間苯二酚二縮水甘油醚、酞酸二縮水甘油酯、新戊二醇二縮水甘油醚、聚丙二醇二縮水甘油醚、四溴雙酚A-二縮水甘油醚、雙酚六氟丙酮二縮水甘油醚、季戊四醇二縮水甘油醚、三-(2,3-環氧丙基)三聚異氰酸酯、單烯丙基二縮水甘油基三聚異氰酸酯、二甘油聚二縮水甘油醚、季戊四醇聚縮水甘油醚、1,4-雙(2,3-環氧丙氧基全氟異丙基)環己烷、山梨糖醇酐聚縮水甘油醚、三羥甲基丙烷聚縮水甘油醚、間苯二酚二縮水甘油醚、1,6-己二醇二縮水甘油醚、聚乙二醇二縮水甘油醚、苯基縮水甘油醚、p-叔丁基苯基縮水甘油醚、己二酸二縮水甘油醚、o-酞酸二縮水甘油醚、二溴苯基縮水甘油醚、1,2,7,8-二環氧辛烷、1,6-二羥甲基全氟己烷二縮水甘油醚、4,4’-雙(2,3-環氧丙氧基全氟異丙基)二苯基醚、2,2-雙(4-環氧丙氧基苯基)丙烷、3,4-環氧環己基甲基-3’,4’-環氧環己烷羧酸酯、3,4-環氧環己基環氧乙烷、2-(3,4-環氧環己基)-3’,4’-環氧-1,3-二噁烷-5-螺環己烷、1,2-伸乙基二氧基-雙(3,4-環氧環己基甲烷)、4’,5’-環氧-2’-甲基環己基甲基-4,5-環氧-2-甲基環己烷羧酸酯、乙二醇-雙(3,4-環氧環己烷羧酸酯)、雙-(3,4-環氧環己基甲基)己二酸酯,及雙(2,3-環氧環戊基)醚等。另外縮水甘油基丙烯酸酯、縮水甘油基甲基丙烯酸酯等之具有環氧基之(甲基)丙烯酸酯的共聚物也可作為上述環氧化合物用。 [0035] 上述環氧化合物可由市售品取得,例如Epo Lead [註冊商標]GT-401、GT-403、GT-301、GT-302、PB3600、CELLOXIDE[註冊商標]2021P、2000、3000、EHPE3150、EHPE3150CE、CYCLOMER[註冊商標]M100(以上為DAICAL製)、EPICLON[註冊商標]840、840-S、N-660、N-673-80M(以上為DIC(股)製)。 [0036] 本發明之感光性接著劑組成物為含有光酸發生劑時,該光酸發生劑如,IRGACURE[註冊商標]PAG103、PAG108、PAG121、PAG203、CG1725、GSID-26-1(以上為BASF公司製)、WPAG-145、WPAG-170、WPAG-199、WPAG-281、WPAG-336、WPAG-367(以上為和光純藥工業(股)製)、TFE三嗪、TME-三嗪、MP-三嗪、二甲氧基三嗪、TS-91、TS-01(三和化學(股)製)。 [0037] 本發明之感光性接著劑組成物為含有熱酸發生劑時,該熱酸發生劑如,K-PURE[註冊商標]TAG-2689、TAG-2690、TAG-2700、CXC-1612、CXC-1614、CXC-1615、CXC-1821(以上為king Industries公司製)。 [0038] 本發明之感光性接著劑組成物為含有無機填料時,該無機填料如,二氧化矽、氮化鋁、氮化硼、氧化鋯、氧化鋁等之溶膠。 [0039] 本發明之感光性接著劑組成物為含有表面活性劑時,該表面活性劑如,聚環氧乙烷月桂醚、聚環氧乙烷硬脂醚、聚環氧乙烷十六醚、聚環氧乙烷油醚等之聚環氧乙烷烷基醚類、聚環氧乙烷辛基苯基醚、聚環氧乙烷壬基苯基醚等之聚環氧乙烷烷基芳基醚類、聚環氧乙烷-聚環氧丙烷嵌段共聚物類、山梨糖醇酐單月桂酸酯、山梨糖醇酐單棕櫚酸酐、山梨糖醇酐單硬脂酸酯、山梨糖醇酐單油酸酯、山梨糖醇酐三油酸酯、山梨糖醇酐三硬脂酸酯等之山梨糖醇酐脂肪酸酯類、聚環氧乙烷山梨糖醇酐單月桂酸酯、聚環氧乙烷山梨糖醇酐單棕櫚酸酯、聚環氧乙烷山梨糖醇酐單硬脂酸酯、聚環氧乙烷山梨糖醇酐三油酸酯、聚環氧乙烷山梨糖醇酐三硬脂酸酯等之聚環氧乙烷山梨糖醇酐脂肪酸酯等之非離子系表面活性劑。 [0040] 上述表面活性劑可由市售品取得,例如F-top[註冊商標]EF301、EF303、EF352(以上為三菱材料電子化成(股)製)、MEGAFAC[註冊商標]F171、F173、R-30、R-30N、R-40、R-40-LM(以上為DIC(股)製)、FLUORAD FC430、FC431(以上為住友3M(股)製)、Asahi Guard[註冊商標]AG710、Sunflon[註冊商標]S-382、SC101、SC102、SC103、SC104、SC105、SC106(以上為旭硝子(股)製)等之氟系表面活性劑,及有機矽氧烷聚合物KP341(信越化學工業(股)製)。該等表面活性劑可單獨使用,或二種以上組合使用。 <接著方法> [0041] 使用本發明之感光性接著劑組成物,經由下述步驟,即,將本發明之感光性接著劑組成物塗佈於第一基板上的步驟,以50℃至160℃之溫度將塗佈於前述第一基板上之感光性接著劑組成物預熱的步驟、將前述預熱後形成於前述第一基板上之塗膜曝光的步驟,將前述曝光後之前述塗膜顯像的步驟,及前述顯像後將第二基板貼合於前述第一基板後,加熱使前述塗膜熱硬化的步驟,可使基板相互間接合。 [0042] 將本發明之感光性接著劑組成物塗佈於第一基板的方法如,旋塗法、槽塗法、浸漬法、流塗法、噴墨法、噴霧法、棒塗法、照相凹版法、縫塗法、輥塗法、轉印法、刷塗法、刮塗法、及氣動刀塗法。 [0043] 塗佈本發明之感光性接著劑組成物的第一基板,及貼附於該第一基板的第二基板如,被覆氧化矽膜、氮化矽膜或氧化氮化矽膜之矽晶圓、氮化矽基板、石英基板、水晶基板、無鹼玻璃基板、低鹼玻璃基板、結晶化玻璃基板、銦錫氧化物(ITO)膜或銦鋅氧化物(IZO)膜所形成之玻璃基板,及聚對苯二甲酸乙二醇酯(PET)、聚萘二甲酸乙二醇酯(PEN)、三乙醯基纖維素(TAC)、聚乙烯(PE)、聚醯亞胺(PI)、聚醯胺(PA)、聚氯乙烯(PVC)、聚環烯烴(PCO)、聚偏氯乙烯(PVDC)、聚乙烯醇(PVA)、聚丙烯(PP)、聚碳酸酯(PC)、聚苯乙烯(PS)、聚丙烯腈(PAN)、伸乙基乙酸乙烯共聚物(EVA)、伸乙基乙烯醇共聚物(EVOH)、伸乙基甲基丙烯酸共聚物(EMMA)或聚甲基丙烯酸(PMMA)所形成之基板。 [0044] 前述預熱之目的為,由塗佈於前述第一基板上之感光性接著劑組成物去除溶劑,結果可於前述基板上由該組成物形成喪失流動性之塗膜。 [0045]於前述塗膜曝光之步驟後及該塗膜顯像之步驟前,必要時例如可以50℃至160℃之溫度進行曝光後加熱(Post Exposure Bake,簡稱PEB)。 [0046] 前述塗膜曝光時所使用之光源如,g線、h線、i線、ghi線寬頻,及KrF準分子雷射。 [0047] 前述塗膜顯像時所使用之顯像液如,鹼性水溶液,及前述感光性接著劑組成物所含之溶劑。鹼性水溶液如,氫氧化鉀、氫氧化鈉等之鹼金屬氫氧化物的水溶液、氫氧化四甲基銨、氫氧化四乙基銨、膽鹼等之氫氧化四級銨的水溶液、乙醇胺、丙基胺、伸乙基二胺等之胺水溶液。顯像液另可使用微影步驟中所使用的作為光阻溶液之溶劑用的已知之有機溶劑。該有機溶劑如,丙二醇-1-單甲基醚2-乙酸酯、1-甲氧基-2-丙醇、環己酮、及2-丙醇。該等有機溶劑可單獨使用,或二種以上組合使用。 [0048] 前述塗膜顯像後,將第二基板貼附於前述第一基板,其後將前述塗膜加熱硬化時之加熱溫度如180℃至240℃,加熱時間如30分鐘至2小時。又,第二基板貼附於前述第一基板時較佳以100℃至200℃加熱。 實施例 [0049] 下面將基於實施例更詳細說明本發明,但本發明非限定於該等實施例。 [0050] 下面所記載之合成例所得的聚合物之GPC分析為使用下述裝置,又,測定條件如下所述。 裝置:一體型高速GPC系統 HLC-8220GPC 東索(股)製 管柱:KF-G,KF804L 管柱溫度:40℃ 溶劑:四氫呋喃(THF) 流量:1.0mL/分 標準試驗:聚苯乙烯 檢波器:RI <合成例1> [0051] 將1,2-環己烷二羧酸127.99g、單烯丙基二縮水甘油基三聚異氰酸175.00g,及苄基三乙基銨氯化物7.20g溶解於丙二醇1-單甲基醚2-乙酸酯465.28g後,140℃下反應4小時得含有聚合物之溶液。將所得溶液冷卻至室溫後,將甲基丙烯酸縮水甘油酯28.71g及苄基三乙基銨氯化物1.15g溶解於本溶液,再以140℃反應3小時得含有聚合物之溶液。所得聚合物進行GPC分析的結果為,標準聚苯乙烯換算下之重量平均分子量為3,500。推斷所得聚合物為,具有下述式(1a)所表示之結構單位及末端具有下述式(2a)所表示之結構的聚合物。<合成例2> [0052] 將1,2-環己烷二羧酸146.27g、單烯丙基二縮水甘油基三聚異氰酸200.00g,及苄基三乙基銨氯化物4.11g溶解於丙二醇1-單甲基醚2-乙酸酯350.38g後,以140℃反應4小時得聚合物之溶液。所得聚合物進行GPC分析的結果為,標準聚苯乙烯換算下重量平均分子量為3,100。推斷所得聚合物為,具有下述式(1a)所表示之結構單位的聚合物。<合成例3> [0053] 將1,2-環己烷二羧酸138.15g單烯丙基二縮水甘油基三聚異氰酸200.00g及苄基三乙基銨氯化物4.11g溶解於丙二醇1-單甲基醚2-乙酸酯342.26g後,以140℃反應4小時得含有聚合物之溶液。所得聚合物進行GPC分析的結果為,標準聚苯乙烯換算下重量平均分子量為4,100。推斷所得聚合物為,具有下述式(1a)所表示之結構單位的聚合物。<調製例1> [0054] 將合成例1所得含有聚合物之溶液注入填充陽離子交換樹脂(15JWET, ORGANO(股)及陰離子交換樹脂(Monosphere 550 A, Muromachi Technos(股))之瓶中,攪拌4小時。 <調製例2> [0055] 將合成例2所得含有聚合物之溶液注入填充陽離子交換樹脂(15JWET, ORGANO(股)及陰離子交換樹脂(Monosphere 550A, Muromachi Technos(股))之瓶中,攪拌4小時。 <調製例3> [0056] 將合成例3所得含有聚合物之溶液注入填充陽離子交換樹脂(15JWET, ORGANO(股))及陰離子交換樹脂(Monosphere550, Muromachi Technos(股))之瓶中,攪拌4小時。 <實施例1> [0057] 將調製例1所得含有聚合物之溶液3.2g、調製例2所得含有聚合物之溶液10.40g、IRGACURE[註冊商標]OXE01(BASF公司製)0.022g、三環癸烷二甲醇二丙烯酸酯(新中村化學工業(股)製)0.33g,及季戊四醇四(3-巰基丁酸酯)(昭和電工(股)製)0.055g溶解於丙二醇1-單甲基醚2-乙酸酯5.53g調製組成物。其後使用孔徑3μm之聚乙烯製微濾器進行過濾,調製感光性接著劑組成物。調製例1與調製例2之聚合物固體成分的質量比為1:3。 <實施例2> [0058] 將調製例1所得含有聚合物之溶液3.5g、調製例2所得含有聚合物之溶液17.30g、IRGACURE[註冊商標]OXE01 BASF公司製)0.023g、三環癸烷二甲醇二丙烯酸酯(新中村化學工業(股)製)0.34g,及季戊四醇四(3-巰基丁酸酯)(昭和電工(股)製)0.056g溶解於丙二醇1-單甲基醚2-乙酸酯8.28g調製組成物。其後使用孔徑3μm之聚乙烯製微濾器進行過濾,調製感光性接著劑組成物。調製例1與調製例2之聚合物固體成分的質量比為1:5。 <實施例3> [0059] 將調製例1所得含有聚合物之溶液2.0g,調製例2所得含有聚合物之溶液13.35g、IRGACURE[註冊商標]OXE01(BASF公司製)0.014g、三環癸烷二甲醇二丙烯酸酯(新中村化學工業(股)製)0.21g,及季戊四醇四(3-巰基丁酸酯)(昭和電工(股)製)0.035g溶解於丙二醇1-單甲基醚2-乙酸酯5.08g調製組成物。其後使用孔徑3μm之聚乙烯製微濾器進行過濾,調製感光性接著劑組成物。調製例1與調製例2之聚合物固體成分的質量比為1:6。 <實施例4> [0060] 將調製例1所得聚合物之溶液1.5g、調製例3所得含有聚合物之溶液13.34g、IRGACURE[註冊商標]OXE01(BASF公司製)0.010g、三環癸烷二甲醇二丙烯酸酯(新中村化學工業(股)製)0.15g,及季戊四醇四(3-巰基丁酸酯)(昭和電工(股)製)0.024g溶解於丙二醇1-單甲基醚2-乙酸酯5.49g調製組成物。其後使用孔徑3μm之聚乙烯製微濾器進行過濾,調製感光性接著劑組成物。調製例1與調製例3之聚合物固體成分的質量比為1:9。 <比較例1> [0061] 將調製例1所得含有聚合物之溶液8.0g、調製例2所得含有聚合物之溶液7.85g、IRGACURE[註冊商標)OXE01(BASF 公司製)0.052g、三環癸烷二甲醇二丙烯酸酯(新中村化學工業(股)製)0.77g,及季戊四醇四(3-巰基丁酸酯)(昭和電工(股)製)0.013g溶解於丙二醇1-單甲基醚2-乙酸酯6.5lg調製組成物。其後使用孔徑3μm之聚乙烯製微濾器,調製光硬化性樹脂組成物。調製例1與調製例2之聚合物固體成分的質量比為1:1。本比較例為(B)成分之聚合物的含量與前述(A)成分之聚合物的含量相同。 <比較例2> [0062] 將調製例1所得含有聚合物之溶液12.0g、調製例2所得含有聚合物之溶液3.53g、IRGACURE[註冊商標]OXE01)BASF公司製)0.077g、三環癸烷二甲醇二丙烯酸酯(新中村化學工業(股)製)1.16g,及季戊四醇四(3-巰基丁酸酯)(昭和電工(股)製)0.19g溶解於丙二醇1-單甲基醚2-乙酸酯6.71g調製組成物。其後使用孔徑3μm之聚乙烯製微濾器進行過濾,調製光硬化性樹脂組成物。調製例1與調製例2之聚合物固體成分的質量比為1:0.3。本比較例為(B)成分之聚合物的含量比前述(A)成分之聚合物的含量少。 <比較例3> [0063] 將調製例1所得含有聚合物之溶液14.0g、IRGACURE[註冊商標]OXE01(BASF公司製)0.090g、三環癸烷二甲醇二丙烯酸酯(新中村化學工業(股)製)1.36,及季戊四醇四(3-巰基丁酸酯)(昭和電工(股)製)0.23g溶解於丙二醇1-單甲基醚2-乙酸酯6.31g調製組成物。其後使用孔徑3μm之聚乙烯製微濾器進行過濾,調製光硬化性樹脂組成物。本比較例為,不含(B)成分之聚合物。 <比較例4> [0064] 將調製例2所得含有聚合物之溶液14.0g溶解於丙二醇1-單甲基醚2-乙酸酯5.17g調製組成物。其後使用孔徑3μm之聚乙烯製微濾器進行過濾,調製樹脂組成物。本比較例為,不含(A)成分之聚合物及(C)成分之自由基型光聚合引發劑。 [相對於溶劑之溶出試驗] [0065] 使用旋塗機將實施例1至實施例4調製之感光性接著劑組成物塗佈於矽晶圓上,以100℃預熱後,使用Aligner(PLA-501, CANNON(股)製)曝光(i線,曝光量:500mJ/cm2
),再以100℃加熱,其後使用NMD-3(東京應化工業(股)製)顯像,再以200℃加熱形成膜厚5μm之膜。23℃下將該膜浸漬於N-甲基2-吡咯烷酮中1分鐘。確認由實施例1至實施例4調製之感光性接著劑組成物所形成之膜為,浸漬前後之膜厚變化為5%以下,因此具有充分耐溶劑性。 [顯像性試驗] [0066] 使用旋塗機將實施例1至實施例4調製之感光性接著劑組成物,比較例1至比較例3調製之光硬化性樹脂組成物,及比較例4調製所得之樹脂組成物塗佈於矽晶圓上,以100℃預熱後,使用Aligner(PLA-501,CANNON(股)製)曝光(i線,曝光量:500mJ/cm2
),再以100℃加熱,其後使用NMD-3(東京應化工業(股)製)顯像。測定曝光部及未曝光部之顯像前後的膜厚,算出殘膜率[(顯像後之膜厚/顯像前之膜厚)×100],結果如下述表1所示。 [表1]
[0067] 由表1所示結果得知,實施例1至實施例4調製之感光性接著劑組成物中曝光部會殘留膜,未曝光部未殘留膜,因此確認具有製圖性。又,比較例1至比較例3調製之光硬化性樹脂組成物,比較實施例1至實施例4調製之感光性接著劑組成物時,因顯像成分之比例較少,故無法充分顯像去除未曝光部而殘留膜。比較例4調製之樹脂組成物因未含光硬化成分,故既使曝光部也未殘留膜。 [接著力評估] [0068] 使用旋塗機將實施例1,實施例3及實施例4調製之感光性接著劑組成物塗佈於4英寸矽晶圓上,以100℃預熱後,使用Aligner(PLA-501,CANNON(股)製)曝光(i線,曝光量:500mJ/cm2
),再以100℃加熱,其次使用NMD-3顯像形成膜厚5μm之膜。其後使用貼合裝置(AYUMI工業(股)製,VJ-300),於真空度10Pa以下,溫度160℃,貼合壓力1200kg之條件下,將前述矽晶圓接著於4英寸玻璃晶圓後,以200℃加熱使前述膜硬化,使用切粒裝置(Disco(股)製,DAD321)切斷該接著後之2枚晶圓的1cm角,製作接著力評估樣品。將Araldite[註冊商標]2014(Huntsman Advanced Materials公司製)塗佈於所得接著力評估樣品之雙面上,以接著力(剪切)測定用專用夾具接著前述樣品之雙面後,使用夾子(島津製作所(股)製,夾子AGS-100NX評估接著力(剪切)。接著力係以5mm/分之拉伸速度測定。結果如下述表2所示。表2中接著力之值為2000N以上時係表示,於Araldite2014塗佈部發生樣品斷裂,但實施例1,實施例3及實施例4調製之感光性接著劑組成物的塗佈部未斷製,故本感光性接著劑組成物之接著力具有表2所記載之數值以上的接著力。使用實施例1,實施例3及實施例4調製之感光性接著劑組成物所得的樣品確認為,具有充分之接著性。 [表2]
Claims (6)
- 一種感光性接著劑組成物,其為含有下述(A)成分、(B)成分、(C)成分及(D)成分,且就質量比而言比較前述(A)成分含有更多前述(B)成分, (A)成分:具有下述式(1)所表示之結構單位,末端具有下述式(2)所表示之結構的聚合物, (B)成分:具有前述式(1)所表示之結構單位,末端具有羧基或羥基的聚合物, (C)成分:自由基型光聚合引發劑, (D)成分:溶劑(該等式中,X表示碳原子數1至6之烷基、乙烯基、烯丙基或縮水甘油基,m及n表示各自獨立之0或1,Q表示碳原子數1至16之二價烴基,Z表示碳原子數1至4之二價連結基,該二價連結基係與前述式(1)中之-O-基鍵結,R1 表示氫原子或甲基)。
- 如請求項1之感光性接著劑組成物,其中前述式(1)中Q所表示之二價烴基為,表示直鏈狀或支鏈狀之伸烷基,含有以雙鍵鍵結之2個碳原子的基,或主鏈含有可具有至少1個取代基之脂環式烴基或芳香族烴基的基。
- 如請求項1或請求項2之感光性接著劑組成物,其中前述式(2)中Z所表示之二價連結基為,表示可具有至少1個作為取代基用之羥基的直鏈狀或支鏈狀之伸烷基。
- 如請求項1至請求項3中任一項之感光性接著劑組成物,其中前述(A)成分與前述(B)成分之質量比為1:2至1:20。
- 如請求項1至請求項4中任一項之感光性接著劑組成物,其中另含有二官能(甲基)丙烯酸酯及/或多官能硫醇。
- 一種接著方法,其為具有將如請求項1至請求項5中任一項之感光性接著劑組成物塗佈於第一基板上的步驟,以50℃至160℃之溫度預熱塗佈於前述第一基板上之感光性接著劑組成物的步驟、前述預熱後將形成於前述第一基板上之塗膜曝光的步驟、前述曝光後將前述塗膜顯像的步驟,及前述顯像後將第二基板貼附於前述第一基板後加熱,使前述塗膜熱硬化的步驟。
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