TW201120171A - Adhesive composition, semiconductor device suing the composition and fabricating method thereof - Google Patents
Adhesive composition, semiconductor device suing the composition and fabricating method thereof Download PDFInfo
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- TW201120171A TW201120171A TW099138872A TW99138872A TW201120171A TW 201120171 A TW201120171 A TW 201120171A TW 099138872 A TW099138872 A TW 099138872A TW 99138872 A TW99138872 A TW 99138872A TW 201120171 A TW201120171 A TW 201120171A
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- resin
- adhesive composition
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- adhesive
- bis
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Classifications
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Description
201120171 ,r 六、發明說明: 【發明所屬之技術領域】 本發明是有關於一種黏著劑組成物、使用該組成物的 半導體裝置及其製造方法。 【先前技術】 具有多層地積層的多個晶片的堆疊封裝型半導體裝置 被用於記憶體(memory)等的用途中。製造半導體裝置時, 為了將半導體元件彼此或半導體元件與半導體元件裝載用 支撐部件黏著,一直應用膜狀黏著劑。近年來,伴隨著電 子零件的小型化、低背化,不斷要求該半導體用的 著劑進-步薄膜化。但是,於半導體元件解導 載用支撐部件上存在由配線等引起的凹凸時,特別是若使 用薄膜化至10 μιη厚以下程度的膜狀黏著劑,則有將黏著 劑貼附於被黏著體時產生空隙,導致可靠性下降的傾^。 另外,製造10 μιη厚以下的膜狀黏著劑自身困難,經薄膜 化的膜的對晶圓的貼附性或熱壓接性下降,故使 沾 半導體裝置的製作困難。 μ 為了解決該些問題,例如研究出了以下方法:如 文獻^般,將含有溶劑的黏著劑組成⑯(樹脂糊) 被黏著體,藉由加熱乾燥使所塗佈的細旨糊B•階段、 [先前技術文獻] [專利文獻] [專利文獻1]日本專利特開·7_n_9號公報 然而,於使用含有溶劑的樹脂糊時,有為了使溶劑揮 201120171 =2了】;二化需要長時間、或半導體晶圓被溶劑污染 進行問題:由於為了使溶騎發的乾燥而 的情形時:膠的膠帶的晶圓上塗佈樹脂糊 於低、、田下二帶…、法谷易地剝離、或產生晶圓的麵曲。若 p狀:f則雖可在某種程度上抑制由加熱導致的不 此時殘存溶劑變多,故有於加熱硬化時產生空 使用雜下降賴向。若為了降低乾燥溫度而 傾向。= 有於使用過程中黏度大幅度地變化的 勸’亦有錢時由鄕著劑表面的賴揮發而於 黏者劑層内部殘存溶劑,故可靠性下降的傾向。 【發明内容】 接板ίϊ暇繁於如上所述的狀況而成,其主要目的在於 '、 可維持半導體裝置的高可靠性、並且使將半導I* 晶片與支樓部件或其他半導體晶片黏著的黏 的黏著劑組成物。 本發明是有關於-種黏著劑組成物,該黏著劑組成物 含有放射線聚合性化合物、光起始劑及熱硬化性樹脂 於將半導體晶片黏著。於藉由光照射使形成黏著劑層的該 黏著劑組成物進行了 B-階段化時,該黏著劑層表面的黏^ 於 30。(:為 200 gf/cm2 以下,於 12(rc 為 2〇〇 gf/cm2 以上。 本發明,黏著劑組成物具備上述構成,藉此可維持半 導體裝置的高可靠性,並且使將半導體晶片與支撐部件或 其他半導體晶月黏著的黏著劑的層更薄。特別 逾 層表面的黏力於30t為200 gf/cm2以下,藉此經B_階段化 4 201120171 後的操作性優異,此外可防止發生以下問題:切割時水滲 入至黏著劑與被黏著體的界面而產生晶片飛濺,切割後與 切割片的剝離性下降而拾取性下降。另外,於12〇。〇之黏 力為200 gf/cm2以上,藉此可獲得良好的熱壓接性,避免 熱壓接時產生空隙、熱壓接溫度變高的問題,可維持半導 體裝置的南可靠性。 藉由光照射而B-階段化的黏著劑組成物的5%重量減 少溫度較佳為15〇t以上。 藉由光照射而B-階段化之前的黏著劑組成物於25〇c 的黏度較佳為1〇11^*3〜3000〇11^*3。 藉由該黏著劑組成物將半導體晶片黏著於被黏著體 時’較佳為半導體晶片與被黏著體之剪切黏著強度於 260°C為 0_2MPa 以上。 藉由光照射而B-階段化後進一步藉由加熱而硬化的 黏著劑組成物的5%重量減少溫度較佳為260°C以上。 放射線聚合性化合物較佳為包含單官能(曱基)丙烯酸 酉旨。該單官能(曱基)丙烯酸酯較佳為包含具有醯亞胺基的 (甲基)丙婦酸醋。 黏著劑組成物較佳為含有具有醯亞胺基的化合物。具 有酿亞胺基的化合物可為聚醯亞胺樹脂之類的熱塑性樹 月曰或具有酸亞胺基的(曱基)丙婦酸g旨等的低分子化合物。 於另一侧面,本發明是有關於一種半導體裝置的製造 方法。本發明的製造方法包括以下步驟:於半導體晶圓的 背面上塗佈上述本發明的黏著劑組成物;藉由光照射使所
201120171 x I 及於本=,、成起斷’切分成多辦導體晶片;以 片與續部件或其他半導體晶片之間夾持黏 者知、、且成物並進行壓接,藉此加以黏著。 % 另外’本發明是有關於一種可藉由上述本發明 導體裝置。本發明的半導體裝置即便於ί 件或其他半導體晶片黏著的黏著劑的 屑溥時,亦具有充分高的可靠性。 [發明的效果] 根據本發明,較使將半導體晶#蚊#部件或其他 半導體晶#料的料細層變料,亦 古 的半導體錢。 μ ▲為讓本發明之上述和其他目的、特徵和優點能更明顯 易懂,下讀舉較佳實闕,並配合賴圖式,作詳細說 明如下。 【實施方式】 以下,視需要一邊參照圖式,一邊對用以實施本發明 的形態加以詳細說明。然而,本發明不限定於以下的實施 形態。圖式中,對相同或相當的要素標註相同符號,適當 省略重複的說明。上下左右等的位置關係只要無特別說 明,則疋基於圖式所示的位置關係。尺寸比率不限於圖示 的比率。 圖1〜圖12是表示半導體裝置的製造方法的一實施形 態的示意圖。本實施形態的製造方法主要由以下步驟構成。 6
It 201120171 步驟1 (圖1):在形成於半導體晶圓1内的半導 片(半導體元件)2的電路面S1上,積層可剝離的膠 , 面研磨膠帶)4。 (背 步驟2 (圖2):對半導體晶圓1自與電路面Sl為相 反側的面(背面)S2進行研磨,使半導體晶圓1變薄:目 步驟3 (圖3):於半導體晶圓i的背面S2塗佈f 劑組成物5。 '考
步驟4 (圖4):自所塗佈的黏著劑組成物即黏著劑層 5側進行曝光’使黏著劑組成物B-階段化。 S 步驟5(圖5):於黏著劑層5上積層可剝離的膠帶(切 割膠帶)6。 步驟6 (圖6):將背面研磨膠帶4剝離。 半導ίΪ片7 ;圖7):藉由切割將半導體晶圓1切分成多個 圖8、圖9、圖1〇):拾取半導體晶片2並壓 導體元件裝制的支撐部件7或其他半導 虚去(圖11):將所安裝的半導H經由導線16 /、支撐σ卩件7上的外部連接端子連接。 片2的圖12》藉由密封材17將含有多個半導體晶 片的積層體密封,獲得半導體裝置1〇〇。 步驟1 (圖1) S1側積層背面研磨膠帶4。 塵預先成形為臈狀的膠帶的 於半導體晶圓1的電路面 月面研磨膠帶的積層可藉由層 201120171 JUUJ^pif 方法來進行。 步驟2 (圖2) 對半導體晶圓1的與背面研磨膠帶4為相反側的面(背 面S2)進行研磨,使半導體晶圓i變薄至取的厚度。研 磨是於藉“®研磨膠帶4將半導體晶圓丨固定於研磨用 的夾具的狀態下使用研磨裝置8進行。 步驟3 (圖3) 研磨後’於半導體晶圓1的背面S2塗佈黏著劑組成 勿5。塗佈可於箱20内將貼附有背面研磨膠帶4的半導體 晶圓1固定於夾具21的狀態下進行。塗佈方法是選自印刷 法、旋塗法、喷塗法、間隙塗佈法、噴射點膠法加_觀 method)、圓塗法及喷墨法等。該些中,就薄膜化及膜厚均 勻性的觀點而言,較佳級塗法或喷塗法。旋塗裝置所具 有的吸附自巾亦可形成有孔,吸附台亦可為離。就吸附 痕不易殘留的觀點而言,吸附台較佳為網狀。關於利用旋 塗法的塗佈’為了防止晶圓的起伏、及邊緣部的隆起,較 ,為以50G rpm〜5_ rpm的轉速進行。就同樣的觀點而 °轉速更佳為1〇〇〇印111〜4000 rpm。亦可於旋塗台上具 備溫度調節器以調整黏著劑組成物的黏度。 八 可將黏著劑組成物保存於注射器(syringe)内。此時, 亦可於旋塗裝置的注射ϋ設置部分具備溫度調節器。 於半導體晶圓上藉由例如旋塗法塗佈黏著劑組成物 時’有時會於半導體晶®的邊緣部分P#著乡餘雜著劑組 成物。可將此種多餘的黏著劑於旋塗後利用溶劑等進行清 8 201120171
洗而去除。清洗方法光备<2,丨im ι 晶圓旋轉, 喷出的方法 可,例如可> 點溶劑。 佈裝置的喷出性或薄膜形成性的觀點 關於所塗佈的㈣顏祕的於坑_度,就自塗 “叮狀々从|王的觀點而言,較佳為10 *s ’ 更佳為 30mpa.s〜1〇〇〇〇mPa.s,進 5000 mPa.s ’ 進__步佳為 1〇〇 mpa.s〜 mPa.s〜30000 mPa.s, 而佳為50 mPa.s〜50< 3000 mPa.s ’最佳為200⑽的〜咖地的。若上述黏度 為10 mPa.s以下,則有黏著劑組成物的保存穩定性下降、 或所塗佈的黏著劑組成物中容易產生針孔(pin h〇le)的傾 向。另外,有利用曝光的B-階段化變困難的傾向。若黏度 為30000 mPa.s以上’則有塗佈時薄膜化困難、喷出變困 難的傾向。此處的黏度為於25。(:使用E型黏度計測定的值。 步驟4 (圖4) 自所塗佈的黏著劑組成物即黏著劑層5侧,藉由曝光 裝置9照射活性光線(典型的是紫外線),使黏著劑組成物 B-階段化。藉此可將黏著劑層5固定於半導體晶圓1,並 且減少黏著劑層5表面的黏性。於該階段中,可獲得本實 施形態的附有黏著劑層的半導體晶圓。曝光可於真空下、 氮氣下、空氣下等的環境下進行。為了減少氧阻礙,亦可 於將經脫模處理的聚對苯二曱酸乙二酯(P〇lyethylene terephthalate,PET)膜或聚丙烯膜、聚乙烯膜等的基材積 201120171 層於黏著劑層5上的狀態下進行曝光。亦可隔著經圖案化 的遮罩進行曝光。藉由使用經圖案化的遮罩,可形成熱壓 接時的動性不同的黏者劑層。曝光量就黏性降低及節拍 時間(takt time)的觀點而言較佳為5〇 mJ/cm2〜2麵 mJ/cm2 〇 曝光後的黏著劑層5的膜厚較佳為3〇 以下,更佳 為20 μιη以下,進而佳為1〇 以下,進一步佳為$哗 以下。就熱壓接性或黏著性的觀點而言,膜厚較佳為丨μιη 以上。曝光後的黏著劑層5的膜厚例如可藉由以下方法測 定。首先’藉由旋塗(2000 rpm/10 s、4000卬…如s)將 黏著劑組成物塗佈於矽晶圓上。對所得的塗膜層壓經脫模 處理的PET膜,藉由高精度平行曝光機(〇RC製作所製 造’「EXM-1172_B-〇〇」(商品名))以 1〇〇〇 mJ/cm2 進行曝 光。其後’使用表面粗糙度測定器(小阪研究所製造)測 定黏著劑層的厚度。 曝光後的黏著劑層表面的於30°C的黏力(表面勒力) 較佳為200 gf/cm2以下。藉此,就曝光後的操作性、切割 的容易程度、拾取性的觀點而言足夠優異。當黏力為2〇〇 gf/cm2以下時’可判斷黏著劑組成物已B_階段化。就操作 性或拾取性的觀點而言,曝光後的黏著劑層表面的於3〇它 的黏力更佳為150 gf/cm2以下。 曝光後的黏著劑層表面的黏力是以如下方式測定。首 先’藉由旋塗(2000 rpm/10 s、4000 rpm/20 s)將點著劑 組成物塗佈於矽晶圓上,對所塗佈的黏著劑層使用手動輥
201120171 ^ ^ A X 於室溫下層壓帝人杜邦製造的表面輕剥離劑處理ΡΕΤ (Α-31)。其後,使用高精度平行曝光機(〇Rc製作所製 造,「EXM-1172-B-oo」(商品名))以 1〇〇〇 mj/cm2 自 ρΕτ 側進行曝光。其後,使用Rhesca公司製造的探針黏性試驗 機’於探針直徑為5.1 mm、剝取速度為1〇 mm/s、接觸荷 重為100 gf/cm2、接觸時間為1 s的條件下測定預定溫度(例 如30°C)下的黏著劑層表面的黏力。 若於30°C的上述黏力超過2〇〇 gf/cm2,則有黏著劑層 於室溫下的表面的黏著性過高、操作性下降的傾向,此外 有谷易叙生以下問題的傾向:切割時水滲入至黏著劑層與 被黏著體的界面而產生晶片飛濺,切割後與切割片的剝離 性下降而拾取性下降。 曝光後的黏著劑層表面的於12(TC的黏力較佳為200 gf/cm以上。若該黏力小於2〇〇 gf/cm2,則熱壓接性受損, 有…、壓接時產生空隙、熱壓接溫度變高的傾向。就低溫壓 接性的觀點而言’曝光後的黏著綱表面於12G°C的黏力 更佳為300 gf/cm2以上。 、藉由光照射而B-階段化的黏著劑組成物的5%重量減 夕温度較佳為12G°C以上,更佳為丨贼以上,進而佳為 以上,進—步佳為2〇〇°C以上。為了提高該5%重量 、^ μ度較佳為黏著劑組成物實質上不含溶劑。若5% 少溫度低,财被黏著體壓接後的熱硬化時或回焊 、”’、歷耘時被黏著體容易剥離的傾向,故於熱壓接必 須加熱乾燥。 201120171 5%重量減少溫度是以如下方式測定。藉由旋塗(2000 rpm/10 s、4000 rpm/20 s)將黏著劑組成物塗佈於石夕晶圓 上,對所得的塗膜層壓經脫模處理的PET膜,藉由高精度 平行曝光機(ORC製作所製造,「ΕΧΜ-1172·Β·〇〇」(商品 名))以1000 mJ/cm2進行曝光。其後,對於經階段化的 黏著劑組成物,使用熱重/熱示差同步分析儀(Si〗奈米技 術公司製造,商品名「TG/DTA6300」),於升溫速度 10 C /min、氮氣流(400 ml/min )的條件下測定5%重量減 少溫度。 步驟5 (圖5) 曝光後,對黏著劑層5貼附切割膠帶等的可剝離的膠 帶6。膠帶6可藉由層壓預先成形為膜狀的膠帶的方法而 貼附。 步驟6 (圖6) 繼而,將貼附於半導體晶圓1的電路面的背面研磨膠 帶4剝離。例如可使用藉由照射活性光線(典型的是紫外 線)而黏著性下降的膠帶,自背面研磨膠帶4侧進行曝光 後將其剝離。 步驟7 (圖7) =著切割線D將半導體晶圓1與黏著劑層5 一起切 ^ °,該切割’將半導體晶圓1切分成於各自的背面上 汉有黏著劑層5的多個半導體晶片2。切割是於藉由膠帶 (切割勝帶)6將整體固定於框架(晶圓環)10的狀態下 使用切割刀11來進行。 12 201120171 步驟8(圖8、圖9、圖10) 切割後,藉由固晶裝置12將所切分的半導體晶片2 與黏著劑層5 —起拾取,壓接(安裝)於半導體裝置用的 支撐部件(半導體元件裝載用支撐部件)7或其他半導體 晶片2。塵接較佳為一邊加熱一邊進行。 藉由壓接,將半導體晶片黏著於支撐部件或其他半導 體aa片。半導體晶片與支樓部件或其他半導體晶片的於 260°C的剪切黏著強度較佳為〇 2 MPa以上,更佳為〇 5 MPa以上。若剪切黏著強度小於〇2 Μρ&,則有由於回焊 步驟等的熱歷程而容易發生剝離的傾向。 此處的剪切黏著強度可使用剪切黏著力試驗機 Dage 4000」(商品名)進行測定。更具體而言,例如是 藉由如下方法測定。首先,對㈣於半導體晶_黏著劑 組成物即黏著劑層整個面進行曝光後,切出3 mmx3 見方的半導體晶片。將所切出的附黏著劑層的半導體晶片 載置於預先準備的5 mm><5 mm見方的半導體晶片上,一 邊以100 gf進行加壓’ 一邊於12〇。〇麼接2秒鐘。其後, 於120°C祕箱加熱丨小時,繼而於⑽。c祕箱加熱3 小獲,半導體晶片彼此黏著的樣品。對所得的樣品使 用煎切黏著力試驗機「Dage_4_」(商品名)測定於2 的剪切黏著力。 、 步驟9 (圖11) 13 201120171 步驟10 (圖12) 藉由密封材17將含有半導體晶片2的積層體密封,藉 此可獲得半導體裝置1〇〇。 經由如上步驟,可製造具有將半導體元件彼此、及/ 或半導體元件與半導體元件裝載用支樓部件黏著的構造的 半導體裝置。半導體裝置的構成及製造方法不限定於以上 的實施形態’只要不偏離本發明的主旨則可適當變更。 例如,可視需要而更換步驟1〜步驟7的順序。更具 體而言,可於預先經切割的半導體晶圓的背面上塗佈黏著 劑組成物,其後照射活性光線(典型的是紫外線)使黏著 劑組成物B-階段化。此時,亦可使用經圖案化的遮罩。 亦可將所塗佈的黏著劑組成物於曝光前或曝光後加熱 至120C以下、較佳為i〇〇°c以下、更佳為8〇。〇以下。藉 此了減y殘存的溶劑、水分,另外可進一步降低曝光後的 黏性。 +藉由光照射而B-階段化後進一步藉由加熱而硬化的 黏著劑組成物的5%重量減少溫度較佳為26〇。(:以上。若該 5%重量減少溫度為260°C以下,則有由於回焊步驟等的熱 歷程而容易發生剝離的傾向。 藉由光照射而B-階段化後進一步藉由於12〇。〇、1小 時,繼而於180。(:、3小時的加熱而硬化時的自黏著劑組成 物的逸氣(out gas)較佳為10%以下,更佳為7%以下, 進而佳為5%以下。若逸氣量為10%以上,則有加熱硬化 時容易產生空隙或剝離的傾向。 14 201120171 w ww〆農 逸氣是以如下方式測定。藉由旋塗(2000 rpm/10 s、 4000 rpm/20 s)將黏著劑組成物塗佈於矽晶圓上,對所得 的塗膜利用手動輥層壓經脫模處理的PET膜,藉由高精度 平行曝光機(ORC製作所製造,(商品 名))以1000 mJ7cm2進行曝光。其後,對經Β-階段化的黏 著劑組成物使用熱重/熱示差同步分析儀(SII奈米技術公 司製造’商品名「TG/DTA6300」),於氮氣流(4〇〇 mi/min) 下以升溫速度50°C/min升溫至120°C,於120〇C保持1小 時,進而升溫至180°C ’於18(TC保持3小時,測定藉由上 述程序(program)加熱時的逸氣量。 藉由光照射進行了 B-階段化的黏著劑組成物(黏著劑 層)的於20°C〜30(TC的熔融黏度(黏度)的最小值(最 低炫融黏度)較佳為30000 Pa.s以下。 工逖取低烙融黏度更佳為20000 IVS 18_ Pa.s以下,特佳為15000 Pa.s以下。黏著劑組成物 具有該等翻⑽最低熔融減,藉此可確條著劑層的 更優異的低溫熱壓接性。進而,可對黏著劑層賦予對^ ::的基板等的良好的密接性。上述最低熔融黏度就;喿 性4的觀點而言較理想的是10Pa.s以上。 ” 黏著劑層的於8(TC〜2GG°C的騎減的最小 低炫融黏度)較佳為5_Pa.s以下。藉此, =度下的熱流動性提高,可確保固晶時的良 接 性。另外,上述最健融減更佳為3_ W 此’於對表面形成有階差的基板等的被黏著體於扇。^ 15 201120171 JWjypif 卜的相對較低的溫度下熱壓接半導體晶片時,黏著劑層更 容易充分地嵌埋階差。上述最低熔融黏度更佳為1〇〇〇 A” 以下。藉此,可保持薄的黏著劑層的熱壓接時的良好的流 動性。另外,可進行更低壓下的熱壓接,於半導體晶片極 薄時特別有利。上述最低熔融黏度的下限就 上。若上述最低熔融黏度超過5〇〇〇 Pa,s,則可能由於熱壓 ,時,流_足而無法確保對支縣板或半導體元件等的 $者體的充分_祕。若潤灘从,則此後的半導 t置組裝中無法保持充分的黏著性, =下降的可能性變高。另外,由於為二 == 的流動性而必需高的熱壓接溫度,故有黏著固定後 的+導體7〇件_料對周邊部件的熱損害變大的傾向。 ^ B-階段化的黏著劑層的於脱〜机的熔融黏度 的最大值(最大炼融黏度)較料测pa.s〜i〇〇〇〇〇 二==劑層的良好的自,上述最大 :者附有黏著劑層的半導體晶圓的保存穩定性提 :劑度更佳為30000Pa.s以上。藉此,黏 :、又上升’故利用加a的與切 易/上述最大溶融黏度更佳為50000 著強度充分下降,可確保 保切判〖的獅性。若嶋性良好,則可適當地確 '、心驟後的附黏著劑層的半導體晶片的拾取性。 201120171 ^jk ^ 石丄地取X烙融黏度低於5〇〇〇 Pa*s,則 後的黏著劑層表面的黏力變得過強的傾向。因此,= 由切割使附有黏著劑層的半導體晶圓單片化所得的半^ ,片與黏著劑層-起拾取時,有黏著劑層自切割片的剝離 力過向,故半導體晶片容易破碎的傾向。上述最^熔融黏 ,就抑制半導體晶圓的翹㈣觀點而言較佳為刚 Pa*s以下。 本說明書中’最大溶融黏度及最低炫融黏度是藉由如 ^法敎的值。減,於PET社以匕階段化後的膜厚 成為50卿的方式塗佈黏著劑組成物,對所得的塗膜利用 手純層壓顏減理的PET膜,於室㈣氣下藉由高精 度平行曝光機(ORC製作所製造,(商 时名))以1000 mj/cm2進行曝光,形成經B階段化的黏著 劑層。將所形成的黏著劑層貼合於鐵氟龍(Tefl〇n,註冊 商標)片,以輥(溫度6(TC、線壓4 kgf/cm、進給速度0.5 m/min)加壓。其後將PET膜剝離,於黏著劑層上重疊藉 由曝光而進行了 B_階段化的其他黏著劑層,一邊加壓一^ 積層。反覆進行上述步驟,獲得厚度為約2〇〇 μιη的黏著 劑樣。口。使用黏彈性測定裝置(Rheonietrics Scientific FE 股份有限公司製造,商品名:ARES),將直徑25mm的平 行板作為測定板’於升溫速度為HTC/min、頻率為1 Hz 的=件下,於20°C〜20(TC或2〇t〜30(rc的測定溫度下對 所得的黏著劑樣品的熔融黏度進行測定。根據所得的熔融 黏度與溫度的關係,讀取於2(TC〜6(rc的最大熔融黏度、 17 201120171 ·; 及於80°C〜200°C的最低熔融黏度。 黏著劑組成物例如含有光起始劑及放射線聚合性化合 物。黏著劑組成物較佳為實質上不含溶劑。 光起始劑可使用藉由光照射而生成自由基、酸或鹼等 的化合物。其中’就電子遷移(migration)等的耐腐钮性 的觀點而言,較佳為使用藉由光照射而生成自由基及/或鹼 的化合物。特別就不需要曝光後的加熱處理的觀點或高靈 敏度的觀點而言,可較佳地使用生成自由基的化合物。藉 由光照射而生成酸或鹼的化合物表現出促進環氧樹脂的聚 合及/或反應的功能。 光起始劑對波長365 nm的光的分子吸光係數就靈敏 度提昇的觀點而言,較佳為1〇〇 ml/g.cm以上,更佳為2〇〇 ml/g,cm以上。分子吸光係數可藉由製備樣品的〇〇〇ι質 量%乙腈溶液,並對該溶液使用分光光度計(日立高新技 術公司公司製造,「U-3310」(商品名))測定吸光度而求 出。 生成自由基的化合物例如可列舉:2-苄基-2-二曱基胺 基 -1-(4- 嗎淋基苯基 )-丁酮 _ι ( 2-benzyl-2-dimethylamino-1 -(4-morpholino phenyl)-butanone-l)、2,2-二甲氧基-1,2-二苯基乙烷-1-酮、 1-羥基-環己基-苯基-酿I、2-曱基小(4-(曱硫基)苯基)-2-嗎啉 基丙酮-1、2,4-二乙基噻噸酮、2-乙基蒽醌及菲醌等的芳香 族酮,苯偶醯二曱基縮酮(benzil dimethyl ketal)等的苯 偶醯衍生物,2-(鄰氯苯基)-4,5-二苯基咪唑二聚物 18 201120171 w —-- (2-(〇-chloro phenyl)-4,5-diphenyl imidazole dimer)、2-(鄰 氣笨基)-4,5-二(間曱氧基苯基)咪唑二聚物、2-(鄰氟苯 基)-4,5-苯基咪唑二聚物、2-(鄰甲氧基苯基)-4,5-二苯基咪 唑二聚物、2-(對曱氧基笨基)·4,5-二苯基咪唑二聚物、2,4-二(對曱氧基笨基)-5-苯基咪唑二聚物及2-(2,4-二曱氧基笨 基)-4,5-二苯基咪唑二聚物等的2,4,5-三芳基咪唑二聚物, 9-苯基吖啶及1,7-雙(9,9,-吖啶基)庚烷 (l,7-bis(9,9’-acridinyl)heptane)等的吖啶衍生物,雙(2,6- 二甲氧基笨甲醯基)-2,4,4-三曱基-戊基氧化膦 ( bis(2,6-dimethoxy benzoyl)-2,4,4-trimethyl-pentyl phosphine oxide)及雙(2,4,6_三甲基苯曱醯基)-苯基氧化膦 等的雙醯基氧化膦,肟酯系化合物,馬來醯亞胺化合物。 該等可單獨使用或組合使用兩種以上。 上述光起始劑中’就於不含溶劑的黏著劑組成物中的 溶解性的觀點而言’可較佳地使用2,2-二曱氧基_ι,2-二苯 基乙烷-1-酮、2-苄基-2-二曱基胺基_ι·(4·嗎啉基苯基丁酉同 -1、2,2·二曱氧基qj·二苯基乙烷_丨_酮、2_曱基(曱硫 基)笨基)_2•嗎琳基丙烧_1_酮。另外,就於空氣環境下亦可 藉由曝光而階段化的觀點而言,可較佳地使用2-苄基-2- 二曱基胺基-1-(4-嗎啉基笨基)_丁酮4、2,2_二曱氧基十孓 二苯基乙烷-1-酮、2-曱基甲硫基)苯基)_2_嗎啉基丙 烧-1-@同。 藉由使用利用曝光而生成鹼的化合物(光鹼產生劑), 可進步提尚黏著劑組成物對被黏著體的高溫黏著性及耐 201120171 濕性。作為其理由,-般認為由級產㈣生成的驗作為 環氧樹脂的硬化觸媒而效率佳地發揮侧,藉此可進一步 提高交聯密度,另外所生成的硬化觸媒腐錄板等的情況 少。另外,藉由使黏著劑組成物中含有光鹼產生劑,可提 高交聯密度’可進-步減少高溫放置時的逸氣。進而,一 般認為可使硬化製裎溫度變低,時間變短。 光鹼產生劑只要為藉由輻射線照射而產生鹼的化合 物,則可不受特別限制而使用。所產生的驗就反應性硬 化速度的觀點而言,較佳為強鹼性化合物。更具體而言, 由光驗產生劑所產生的驗於水溶液中的pKa值較佳為7以 上,更佳為8以上。pKa通常是作為鹼性的指標,為酸解 離常數的對數。 藉由輻射線照射而產生的驗例如可列舉:咪唑、2,4-一曱基哺唾、1-甲基咪唑等的咪唑衍生物,哌嗪 (piperazine)及2,5-二曱基哌嗪等的哌嗪衍生物,哌啶 (piperidine)及1,2-二甲基α辰咬等的旅咬衍生物’三甲胺、 三乙胺及三乙醇胺等的三烷基胺衍生物,4_曱基胺基吡啶 及4-二甲基胺基吡啶等的於4位上取代有胺基或烷基胺基 的°比σ定衍生物’吼略烧(pyrr〇lidine)、η_甲基π比略烧等的 °比咯烷衍生物、1,8-二氮雜雙環(5,4,〇)十一碳烯-1 (l,8-diazabiscyclo(5,4,0)undecene-l,DBU)等的脂環族 胺衍生物’苄基甲基胺、苄基二曱基胺及苄基二乙基胺等 的苄基胺衍生物’脯胺酸衍生物,三乙二胺,嗎啉衍生物, 一級烧基胺。 20 201120171 亦可使用藉由活性光線的照射而產生一級胺基的肟衍 生物、作為光自由基產生劑而市售的2-甲基小(4-(曱硫基) 本基)-2-嗎琳基丙烧-Ι-g同(汽巴精化公司製造,irgacure 907)、2-节基-2-二甲基胺基嗎啉基笨基)_丁酮-1 (汽 巴精化公司製造’ Irgacure 369)、3,6-雙-(2-曱基-2-嗎琳基-丙醢基)-9-N-辛基咔唑(ADEKA公司製造,Optomer N-1414)、六芳基聯咪唑衍生物(亦可由鹵素、烷氧基、 硝基、氰基等的取代基取代於苯基上)、苯幷噁唑啉酮衍生 物、胺基曱酸鹽衍生物等作為光起始劑。 如上所述的藉由輻射線照射而產生鹼的光鹼產生劑例 如可使用 Journal of Photop〇lymer Science and Technology 12 卷 313 項〜314 項(1999 年)或 Chemistry of Materials 11 卷170項〜176項(1999年)等所揭示的四級銨鹽衍生物。 該等化合物藉由活性光線的照射而生成鹼性高的三烷基 胺,故最適於環氧樹脂的硬化。 光驗產生劑亦可使用Journal of American Chemical ’ Society 118 卷 12925 頁(1996 年)或 Polymer Journal 28 卷795頁( 1996年)等所揭示的胺基曱酸衍生物。 藉由活性光線的照射而產生鹼的光鹼產生劑可使用: 2,4-二曱氧基-1,2-二苯基乙烷-1-酮、1,2-辛二酮' 苯 硫基)-,2-(0-苯曱醯將)]或乙g同、1-[9-乙基-6-(2-曱基苯曱醯 基)-9H-咔唑-3-基]-,1-(0-乙醯基两)等的肟衍生物或作為光 自由基產生劑而市售的2-节基-2-二曱基胺基-1-(4-嗎啉基 苯基)-丁酮-1、2,2-二曱氧基-1,2-二苯基乙烷-1-酮、2-甲基 21 201120171 OOOJ^pif -1-(4-(甲硫基)苯基)_2·嗎啉基丙烷_丨_酮、2_苄基_2二甲基 胺基-1-(4-嗎啉基苯基)-丁酮-卜六芳基雙咪唑衍生物(亦 可由齒素、烧氧基、硝基、氰基等的取代基取代於苯基上)、 苯幷噁唑啉酮衍生物等。 上述光鹼產生劑亦可使用在高分子的主鏈及/或支鏈 上導入有產生鹼的基的化合物。此時的分子量就作為黏著 劑的黏著性、流動性及耐熱性的觀點而言,重量平均分子 量較佳為1000〜100000,更佳為5000〜30000。 上述光鹼產生劑於未曝光的狀態下不顯示與環氧樹脂 的反應性,故室溫下的儲存穩定性非常優異。 放射線聚合性化合物可列舉具有乙烯性不飽和基的化 合物。乙烯性不飽和基可列舉乙烯基、烯丙基、丙烯基、 丁烯基、乙炔基、苯基乙炔基、馬來酿亞胺基、耐地酿亞 胺基、(曱基)丙烯醯基等。就反應性的觀點而言,較佳為(甲 基)丙烯醯基。放射線聚合性化合物較佳為含有單官能(甲 基)丙烯酸酯。藉由添加單官能(曱基)丙烯酸酯,特別可於 用以進行B-階段化的曝光時降低交聯密度’可使曝光後的 熱壓接性、低應力性及黏著性為良好的狀態。 單官能(曱基)丙烯酸酯的5%重量減少溫度較佳為 l〇〇°C以上,更佳為120。(:以上,進而佳為150〇C以上,進 一步佳為180°C以上。此處的5%重量減少溫度是對放射線 聚合性化合物(單官能(曱基)丙烯酸酯)使用熱重/熱示差 同步分析儀(SII奈米技術製造,TG/DTA6300),於升溫 速度10°C/min、氣氣流(400 ml/min)的條件下測定。藉 22 201120171 由使用5%重量減少溫度高的單官能(曱基)丙烯酸酯,可抑 制藉由曝光而B-階段化後殘存的未反應單官能(曱基)丙稀 酸酯於熱壓接或熱硬化時揮發。 單官能(曱基)丙烯酸酯例如是選自含縮水甘油基的 (曱基)丙烯酸酯、苯酚EO改性(甲基)丙烯酸酯、苯酚p〇 改性(曱基)丙烯酸酯、壬酚EO改性(甲基)丙婦酸酯、壬酚 PO改性(曱基)丙烯酸酯、含酚性羥基的(甲基)丙烯酸酯、 含羥基的(曱基)丙烯酸酯、苯基苯酚縮水甘油醚(曱基)丙烯 酸酯、(甲基)丙稀酸苯氧基乙酯等的芳香族系(甲基)丙稀酸 酉旨、含醯亞胺基的(曱基)丙烯酸酯、含羧基的(甲基)丙烯酸 酯、含異冰片基的(曱基)丙烯酸酯、含二環戊二烯基的(甲 基)丙烯酸酯、(曱基)丙烯酸異冰片酯。 單官能(曱基)丙烯酸酯就B _階段化後與被黏著體的密 接性、硬化後的黏著性、耐熱性的觀點而言,較佳為具有 選自胺基甲酸酯基、異三聚氰酸基、醯亞胺基及減中的 至J 一種g能基。特佳為具有醯亞胺基的單官能(甲基 稀酸酯。 具有環氧基的單官能(曱基)丙稀酸i旨亦可較佳地使 用。具有%氧基的單官能(甲基)丙稀酸醋的5%重量減少溫 度就保存穩定性、黏著性、低逸氣性、耐熱•耐濕可靠性的 觀點而言,較佳為15叱以上,更佳為⑽。C以上,進而佳 以上。具有環氧基的單官能(甲基)丙烯酸酯的5% t少溫度就可抑制膜形成時的由加熱乾燥引起的揮發 或於表面的凝析的觀點的,難為15(rc以上,就 23 201120171 制熱硬化時的由逸氣導致的空隙及剝離或黏著性下降的觀 點而言,更佳為180。〇以上,進而佳為2〇〇。〇以上,就可抑 制回焊時由未反應成分揮發所導致的空隙及剝離的觀點而 言,最佳為26(TC以上。此種具有環氧基的單官能(曱基) 丙烯酸。醋較佳為具有芳香環。藉由使用5%重量減少溫度 為150°C以上的多官能環氧樹脂作為單官能(甲基)丙烯酸 酯的原料,可獲得高耐熱性。 具有%氧基的單官能(甲基)丙烯酸酯並無特別限定, 除了甲基丙賊縮水甘油自旨、_酸縮水甘帥、丙稀酸 冬經基丁 g旨縮水甘_、曱基丙烯酸冬經基丁醋缩水甘油 驗以外,可列舉使具有與環氧基反應的官能基及乙烯性不 飽和基^化合物與多官能環氧樹脂反應所得的化合物等。 上述與環氧基反應的官能基並無特別限定,可列舉異氮酸 醋基、幾基、紛性經基、經基、酸肝、胺基、硫醇基、醯 胺基等。該,化合物可單獨使用一種或組合使用兩種以上。 具有每氧基的單官能(甲基)丙稀酸酯例如是藉由在三 苯基膦或演化四丁基録的存在下,使i分子中具有至少2 個以上的環氧基的多官能環氧樹脂與相對於環氧基1當量 而為〇.1當量〜0.9當量的(甲基)丙婦酸反應而獲得。另 匕卜允亦可藉由在一月桂酸二丁基錫的存在下,使多官能異 狀酉旨化合物與含經基的(甲基)丙婦酸醋及含祕的環氧 化t物反應,或使多官能環氧樹脂與含異氰酸醋基的(甲基) 旨反應,而獲得含縮水甘油基的(甲基)丙烯酸胺基 甲酸酯等。 24
At 201120171 進而,具有核氧基的單官能(甲基)丙湘 子遷移或防止金屬導體電路的腐钱的觀點曰* 電 用將作為雜質離子的驗金屬離子、驗土金二,較佳為使 子特別是氯離子或水解性氣等減少至咖Pt子以 ,度品。例如藉由使用減少了驗金屬離子、驗土金屬離/ 環氧樹脂作為原料’可从上述雜質 離子浪度。總虱含量可依據JISK7243_3來測定。 滿足上述賴性及純度邮有縣絲單 =烯酸酯成分並無❹m定,可列舉將㈣A ( 1 ^、2二型)_水甘_、氫化雙^型縮水甘油 氧乙烧加成物雙紛a及/或f型的縮水甘频、環 加成物㈣A及/或F型_水甘_、苯酴祕 二漆=月曰的縮水甘油鱗、甲酚贿清漆樹脂的縮水甘油 又紛A祕清漆樹脂的縮水甘油趟、萘樹脂的縮水甘 膝―、、二g㈣(或四官能型)的縮水甘㈣、二環戍二 =紛樹脂的縮水甘_、二聚酸的縮水甘油醋、三官能 (或四官能型)的縮水甘油胺、萘樹脂的縮水甘油胺等 竹為原料的化合物。 特別是為了改善熱壓接性、低應力性及黏著性,較佳 ^環氧基及乙稀性不飽和基的個數分別為3個以下,特佳 ’、、、乙,性不飽和基的個數為2個以下。此種化合物並無特 別限定,可較佳地使用下述通式(13)、通式(14)、通式 、(15)、通式(16)或通式(丨7)所表示的化合物等。下述 通式(13)〜通式(17)中,Rl2&Rie表示氫原子或曱基, 25 201120171 ^pif R1G、R11、R13及R14表示二價有機基,R15〜R18表示含環 氧基或乙烯性不飽和基的有機基。 Λ R10—〇
(13) Λ 〇—R11— ^H-CH2—〇—^―C—CHs OH Ο
(14)
如上所述的單官能(曱基)丙烯酸酯的量相對於放射線 聚合性化合物整體量較佳為20質量%〜100質量%,更佳 為40質量%〜100質量%,最佳為50質量%〜100質量 %。藉由使單官能(曱基)丙烯酸酯的量為該範圍,可特別提 昇Β-階段化後的與被黏著體的密接性及熱壓接性。 放射線聚合性化合物亦可含有二官能以上的(曱基)丙 26 201120171 g L二官能以上的(甲基)丙烯酸酯例如是選自二乙二 ° 丙%i文g日(diethylene glycol diacrylate)、三乙二醇一 ^稀酸§旨、四乙二醇二丙烯酸S旨、二乙二醇二甲基丙炼酸 酉曰一乙二醇二曱基丙烯酸酯、四乙二醇二曱基丙烯酸酯、 二經曱基丙烷二丙烯酸酯、三羥甲基丙烷三丙烯酸酯、三 經曱基丙烷二曱基丙烯酸酯、三羥曱基丙烷三曱基丙烯酸 醋、1,4-丁二醇二丙烯酸酯、丨,6_己二醇二丙烯酸酯、l,4-丁二醇二甲基丙烯酸酯、1,6-己二醇二甲基丙烯酸酯、季 戊四醇三丙烯酸酯、季戊四醇四丙烯酸酯、季戊四醇三曱 基丙烯酸酯、季戊四醇四曱基丙烯酸酯、二季戊四醇六丙 烯酸酯、二季戊四醇六曱基丙烯酸酯、笨乙烯(styrene)、 二乙烯基苯(divinyl benzene )、4-乙烯基甲苯(4-vinyl toluene )、4-乙烯基0比咬(4-vinyl pyridine )、N-乙婦基D比口各 炫酮(N-vinylpyrrolidone)、丙烯酸-2-經基乙酯、甲基丙 烯酸-2-羥基乙酯、1,3-丙烯醯氧基-2-羥基丙烷、1,2_甲基 丙烯醯氧基-2-羥基丙烷、亞曱基雙丙烯醯胺、N,N-二甲基 丙烯醯胺、N-羥甲基丙烯醯胺、三(β-羥乙基)異三聚氰酸 酯的三丙烯酸酯、下述通式(18)所表示的化合物、丙烯 酸胺基曱酸酯或甲基丙烯酸胺基曱酸酯、及脲丙烯酸酯。
式(18)中,R19及R2Q分別獨立表示氫原子或曱基, 27 201120171 g及h分別獨立表示1〜20的整數。 該些放射線聚合性化合物可單獨使用一種或組合使用 兩種以上。其中,上述通式(18)所表示的具有二醇骨架 的放射線聚合性化合物於可充分賦予硬化後的耐溶劑性、 且黏度低並且具有南的5%重量減少溫度的方面而言較佳。 另外,若使用官能基當量高的放射線聚合性化合物, 則可實現低應力化、低翹曲化。官能基當量高的放射線聚 合性化合物較佳為聚合官能基當量為200 eq/g以上,更佳 為300 eq/g以上,最佳為400 eq/g以上。藉由使用聚合官 能基當量為200eq/g以上的具有醚骨架、胺基甲酸酯基及/ 或異三聚氰酸基的放射線聚合性化合物,可提高黏著劑組 成物的黏者性且貫現低應力化、低勉曲化。另外,亦可將 聚合官能基當量為200 eq/g以上的放射線聚合性化合物與 聚合官能基當量為200 eq/g以下的放射線聚合性化合物併 用。 放射線聚合性化合物的含量相對於黏著劑組成物總量 較佳為10質量%〜95質量%,更佳為2〇質量%〜9〇質 量% ’最佳為4〇質量%〜90質量%。若放射線聚合性化 合物為10質量%以下’則有B_階段化後_力變大的傾 向,若放射線聚合性化合物為%質量%以上,則有熱硬 化後的黏著強度下降的傾向。 放射線聚合性化合物較佳為於室溫下為液狀。放射線 聚合性化合物_度餘為麵mpa 論.S以下’進而佳為2_mpa.s以下,最佳二為二 28 201120171 从卜t 以下。若放射性聚合性化合物的黏度為5〇〇〇 mPa.s以上, 則有黏著劑組成物的黏度上升而黏著劑組成物的製作變困 難,或薄膜化變困難,或自喷嘴的噴出變困難的傾向。 放射線聚合性化合物的5%重量減少溫度較佳為 120C以上,更佳為15〇。〇以上,進而佳為18〇。〇以上。此 處的5%重量減少溫度是使用熱重/熱示差同步分析儀(sii ,米技術製造,TG/DTA6300)於升溫速度wc/min、氮 氣流(400 ml/min)的條件下對放射線聚合性化合物進行 測疋。藉由應用5%重量減少溫度高的放射線聚合性化合 物,可抑制未反應的放射線聚合性化合物於熱壓接或熱硬 化時揮發。 黏著劑組成物較佳為含有熱硬化性樹脂。熱硬化性樹 脂只要為由藉由熱而引起交聯反應的反應性化合物構成的 成分,則並無特別限定。熱硬化性樹脂例如是選自環氧樹 脂、氰酸酯樹脂、馬來醯亞胺樹脂、烯丙基耐地醯亞胺樹 脂、酚樹脂、脲樹脂、三聚氰胺樹脂、醇酸樹脂、丙烯酸 系樹脂、不飽和聚酯樹脂、鄰苯二曱酸二烯丙酯樹脂、聚 矽氧樹脂、間苯二酚曱醛樹脂、二曱苯樹脂、呋喃樹脂、 聚胺基曱酸酯樹脂、酮樹脂、三聚氰酸三烯丙酯樹脂、聚 異氰酸酯樹脂、含有異三聚氰酸三(2-羥基乙基)酯的樹 脂、含有三偏苯三曱酸三烯丙酯的樹脂、由環戊二烯合成 的熱硬化性樹脂、由芳香族二氰胺的三聚作用所得的熱硬 化性樹脂。其中,與聚醯亞胺樹脂的組合中,就可具有高 溫下的優異黏著力的觀點而言,較佳為環氧樹脂、馬來醯 29 201120171 亞胺樹脂及稀丙基耐地醯亞胺樹脂。再者,該些 樹脂可單獨使用或組合使用兩種以上。 環氧編紐為具有2伽上的環氧基触合物 ,、、、壓接性或魏性、硬錄特性的觀㈣S,較佳 的縮水甘_型的環氧樹脂。此種環氧樹脂例如可列 (或AD型、S型、Fi〇的縮水甘油_ 雙盼A型的縮水甘_、環氧㈣加成物雙❹型的= 甘油趟、魏狀加成物雙驗A型的縮水甘㈣、苯 搭清漆樹脂的縮水甘_、清漆概的縮水 縫、㈣A祕清漆樹脂_水甘_、萘樹脂的縮水甘 油趟、三官能型(或四官能型)的縮水甘_、二二 烯苯酚樹脂的縮水甘油醚、二聚酸的縮水甘油酯、三官= 型(或四官能型)的縮水甘油胺、獅愧的縮水甘油胺此 該等可單獨使用或組合使用兩種以上。 裱氧樹脂就防止電子遷移或防止金屬導體電路的腐姓 的觀點而言,較佳為使驗作為雜f離子的驗金屬離子、 驗土金屬離子、i⑽子特別是_子或水解性氣等減少 至300 ppm以下的高純度品。 環氧樹脂的含量相對於放射線聚合性化合物1〇〇質量 ,較佳為1質量份〜1〇〇質量份,更佳為2質量份〜5〇質 篁份。若該含量超過1〇〇質量份,則有曝光後的黏性上升 的傾向。另-方面,若上述含量少於2質量份,則有難以 獲得充分的熱壓接性及高溫黏著性的傾向。 熱硬化性樹脂較佳為於室溫下為液狀。熱硬化性樹脂 201120171 較佳M_〇mPa.s以下,更佳為簾mpa.s以 佳4 3_悉·8以下,最佳為2_ mPa.s以下。 J 2 1〇_ *以上’則有黏著劑組成物的黏度上 升,薄膜化變困難的傾向。 ^化性樹脂的5%重量減少溫度較佳為赋以 為180C以上,進而佳為2〇(rCj^。此處的5% 術是使賴重/熱示朗步分析儀⑽奈米技 rl ^ ΓΑ_,料溫速度和娜、聽流(400 =)的^件下對熱硬化性樹脂進行測定。藉由應用抓 =減>、溫度高的熱硬化性樹脂’可抑獅熱壓接或執硬 二St具有此種耐熱性的熱硬化性樹脂可列舉ΐ有 :香糊脂。就黏著性、耐熱性的觀點而言,特別 ^地^用二官能型(或四官能型)的縮水甘油胺 齡Α型(或AD型、s型、㈣)的縮水甘油驗。 使用環氧樹脂時,黏著劑組成物較佳為 進劑。硬化促·只要為藉由加熱匕^ 聚合的化合物,則並無特別限制。硬化=二= =糸化合物、脂肪族胺、脂環族胺、芳香 = 脂:族酸酐、脂環族酸針'芳香族酸酐、二氛二:胺 •坐類、二氛二醯胺衍生物、二驗二二 ===I乙基基㈣-‘酸 ·- 1,8-—氮雜雙裱[5.4.〇]十一碳烯_7_四笨 31 201120171 :觀點而S,可較佳地使用咪唑類。硬化促進劑的含量相 、於,氧樹月旨100質量份較佳為0.01質量份〜50質量份。 、咪唑類的反應起始溫度較佳為5〇t以上,更佳為8(rc 進而佳為HC以上。若反應起始溫度為贼以下, ^子穩定性下降,故有㈣敝成物的减上升而膜厚 的控制變困難的傾向。 咪唾類以具有較佳為10μιη以下、更佳為8卿以下、 μιη以下的平均粒徑的粒子為宜。藉由使用此 / L >咪唑類,可抑制黏著劑組成物的黏度變化,另 :抑㈣哇類的沈降。另外,可藉由在薄膜形成時減少表 =的凹凸而獲得均勻的膜。進而—般認為,可於硬化 的硬化均勻地進行’故可減少逸氣。另外,藉由使 %氧樹脂巾的溶解性不佳的„純,可獲得良好的保存 穩定性。 咪唾類亦可使用溶解於環氧樹脂中的味嗤。藉 此種咪唾類,可進-步減少薄膜形成時的表面的凹凸。此 種味嗤類並紐定,可列舉2.乙基I甲基㈣、 _2-甲基咪唑、i-氰乙基么乙基斗甲基咪唑、卜氰乙基^ 笨基咪嗤、u基·2·曱基料、苯基味唾等土。 黏著劑組成物亦可含有紛系化合物作為硬化劑 化合物更佳為於分子中具有至少2個以上的紛性經基的酚 糸化合物。此種化合物例如可列舉笨祕料漆、 酸清漆、第三丁基苯_酸清漆、二環戍二稀甲盼_、生 漆、二環戊二烯苯⑽酸清漆、苯二曱基改性料紛^ 32 201120171 漆、萘酚系化合物、三苯酚系化合物、四苯鹼酴搭清漆、 雙酚A酚醛清漆、聚對乙烯基苯酚、苯酚芳烷基樹脂等。 該些酚系化合物中,較佳為數量平均分子量在400〜4000 的範圍内的化合物。藉此,可於半導體裝置組裝加熱時抑 制導致半導體元件或裝置等的污染的加熱時的逸氣。酚系 化合物的含量相對於熱硬化性樹脂100質量份較佳為50 質量份〜120質量份,更佳為70質量份〜100質量份。 被用作硬化性樹脂的馬來醯亞胺樹脂為具有2個以上 的馬來醯亞胺基的化合物。馬來醯亞胺樹脂例如可列舉下 述通式(IV)所表示的雙馬來醯亞胺樹脂、及下述通式(v) 所表示的酚醛清漆型馬來醯亞胺樹脂:
肪族烴基的二價有機基); 芳香族環及/或直鏈、分支或環狀
33 201120171 (式中,η表示0〜20的整數)。 式(IV)中的R5較佳為笨殘基,曱苯殘基,二曱苯殘 基,萘殘基,直鏈、分支或環狀烷基,或該些基的混合基。 R5更佳為下述化學式所表示的二價有機基。各式中,η為 1〜10的整數。 34 2011201¾
35 201120171
其中,就可賦予黏著膜的硬化後的耐熱性及高溫黏著 力的觀點而言,可較佳地使用具有下述結構的雙馬來醯亞 胺樹脂: 36 201120171
及/或具有下述結構的紛酸清漆型馬來醯亞胺樹脂:
該些式中,η表示〇〜20的整數。 為了進行上述馬來醯亞胺樹脂的硬化,亦可將烯丙基 化,酚A、氰酸酯化合物與馬來醯亞胺樹脂組合。亦可使 黏著劑組成物中含有過氧化物等的觸媒。關於上人 及觸媒的添加量、及添加的有無,是於可確保目標特二的 範圍内適當調整。 稀丙基耐地醯亞胺樹脂為具有2個 醯亞胺基的化合物。例如可列舉下 的和基财地 烯丙基耐地醯亞胺樹脂。 通式⑴所表示的雙 37 201120171
式(i)中,K表示含有芳香相 環狀脂肪族烴的二價有機基。Rl較佳鍵二分支或 曱苯殘基,二甲苯殘基,萘殘基,直鍵w、支;^苯殘^ ’ :該些基的一'更佳為下二==有 機基。各式中’ η為1〜1〇的整數。 38 201120171 -** L L·
39 201120171
其中,下述化學式(II)所表示的液狀的六亞甲基型 雙烯丙基耐地醯亞胺、下述化學式(ΙΠ)所表示的低熔點 (炼點:40。〇固體狀的苯二曱基型雙烯丙基耐地醯亞胺 於以下方面而言較佳:亦作為構成黏著劑組成物的 類的成分_相容劑而發揮作用,可賦予 至/皿下的膜表面的點著性的卜扎 與切割膠帶的易剝離性、# ^㈣性、及拾取時的 觀點而言更佳。 刀割後的切斷面的再熔著的 的嫌動性。另外,固體狀的笨二甲L二 =醯亞胺除了具有良好的熱時流動性以外,可;: 201120171
該些雙烯丙基耐地醯亞胺可單獨使用或組合使用兩種 以上。 烯丙基耐地醯亞胺樹脂於無觸媒條件下的單獨硬化需 要250°C以上的硬化溫度。另外,使用觸媒時,僅可使用 強酸或鏽鹽等可能對電子材料而言成為重大缺陷的金屬腐 蝕性的觸媒,且最終硬化需要25(TC左右的溫度。藉由將 上述烯丙基耐地醯亞胺樹脂與二官能以上的丙烯酸醋化合 物或曱基丙烯酸酯化合物、及馬來醯亞胺樹脂的任一種併 用’可於200°C以下的低溫下硬化(文獻:A.Henner, A.Kramer, “ Allylnadic-Imides: A New Class 〇f Heat-Resistant Thermosets , J.Polym.Sci., par^. ^ Polym.Chem” 27, 1301 (1989))。 黏著劑組成物亦可更含有熱塑性樹脂。藉由使用熱塑 性樹脂’可使低應力性、與被黏著體的密接性、熱壓接性 進一步提昇。熱塑性樹脂的玻璃轉移溫度(Tg)較佳為 15(TC以下’更佳為120°C以下,進而佳為100。(:以下,最 201120171 Juuo^pif 佳為80〇C以下。當該Tg超過15(rc時,有黏著劑組成物 ^黏度上升的傾向。另外,將黏著劑組成物熱壓接於被黏 著體時需I 1耽以上的高溫,而有半導體晶圓易產生_ 曲的傾向。 此處的「Tg」是指經膜化的熱塑性樹脂的主分散波峰 溫度。使用Rheometrics公司製造的黏彈性分析儀「RSA_2」 (商品名)’於膜厚100μιη、升溫速度5〇c/min、頻率1Hz、 測定溫度-150°C〜300°C的條件下測定膜的動態黏彈性,將 tan3的主分散波峰溫度作為Tg。 熱塑性樹脂的重量平均分子量較佳為在5〇⑻〜 500000的範圍内,就可高度地兼具熱壓接性與高溫黏著性 的觀點而言,更佳為10000〜3〇〇〇〇〇。此處的「重量平均 分子量」是指使用島津製作所公司製造的高效液相層析儀 「C-R4A」(商品名)以標準聚苯乙烯換算測定時的重量平 均分子量。 熱塑性樹脂除了聚酯樹脂、聚_樹脂、聚醯亞胺樹脂、 聚醯胺樹脂、聚醯胺醯亞胺樹脂、聚醚醯亞胺樹脂、聚胺 基曱酸酉曰樹脂、聚胺基甲酸g旨醯亞胺樹脂、聚胺基甲酸酯 醯胺醯亞胺樹脂、矽氧烷聚醯亞胺樹脂、聚酯醯亞胺樹脂、 該些樹脂的共聚物、該些樹脂的前驅物(聚醯胺酸等)以 外,可列舉聚苯幷噁唑樹脂、苯氧樹脂、聚礙樹脂、聚醚 颯樹脂、聚苯硫鱗樹脂、聚酯樹脂、聚喊樹脂、聚碳酸酯 樹脂、聚驗酮樹脂、重量平均分子量為1萬〜萬的(甲 基)丙烯酸系共聚物、紛搭清漆樹脂、盼樹脂等。該些可單 42 2011201¾ 種或組合使用兩種以上。另外,亦可對該些樹脂 …鏈及/或支鏈上賦予乙二醇或丙二料的二 及/或羥基。 古f些熱塑性樹脂中,就高溫黏著性、耐熱性的觀點而 二,…塑性樹脂較佳為具有醯亞胺基的樹脂。具有醯亞胺 2樹脂例如可使用選自由聚醯亞胺樹脂、聚ϋ胺醯亞胺 其月曰、聚嶋亞胺獅、聚絲f_醯亞胺樹脂、聚胺 2酸S旨g!麵亞贿脂、魏鮮酿魏細旨及聚醋酿 胺樹脂所組成的組群中的至少一種樹脂。 聚醯亞胺樹脂例如可利用以下方法合成。可藉由公知 ^方法使四賴二酐與二胺進行縮合反應而獲得。即,於 =冷劑中,使四紐二軒與二胺以等莫耳,或視需要相 、,紐二針的合計量1G莫耳以為Q5莫耳〜 呌旦莫耳、更㈣0.8冑耳〜1〇莫耳的範圍對二胺的合 =調整組成比(各成分的添加順序為任意),於反應溫度 以下、雛為於Gt〜6Gt進行加成反應。隨著反應 ^丁而反應液的黏度逐漸上升,生成作為雜亞胺樹脂的 :驅物的輯麟、。再者,為了抑㈣麵錢的各種特 站降,上述四舰二軒較佳為經乙酸㈣行了再結晶 砘化處理的四羧酸二酐。 關於上述縮合反應中的四紐二酐與二胺的組成比, =相對於_酸二_合計量1G莫耳而二胺的合計量超 = 2.0莫耳’财所得的聚酸亞贿财胺末端的聚酿亞 知低聚㈣量好的傾向,且絲醯亞胺樹賴重量平均 43 201120171. = 劑組成物的包括耐熱性的各種特性變得 不充刀的傾向。另-方面,^相對於四賴二酐的合計量 7 胺的合計量未達G.5莫耳’則有酸末端的聚 Μ㈣脂低聚物的量變多的傾向,且有聚醯亞胺樹脂的 重量平均分子量變低,黏著聽成物的包括耐熱性的各種 特性變得不充分的傾向。 聚醯亞胺樹脂可使上述反應物(聚醯胺酸)進行脫水 Ρ魏而獲得。脫水閉環可藉由實施加熱處理的熱閉環法、 使用脫水劑的化學閉環法等來進行。 被用作聚醢亞胺樹脂的原料的四致酸二軒並益特別 制,例如可列舉:均苯四曱酸二肝(ρ抑mellitic dianhydride)、3,3',4,4'-聯苯四甲酸二酐、2,2·,3,3'-聯苯四甲 酸二酐、2,2-雙(3,4-二羧基苯基)丙烷二酐 (2,2-bis(3,4-dicarboxy phenyl)propane dianhydride) > 2,2-雙(2,3-二羧基苯基)丙烷二酐、1,1_雙(2,3_二羧基苯基)乙烷 二酐、1,1-雙(3,4-二羧基苯基)乙烷二酐、雙(2,3_二羧基苯 基)甲烷二酐、雙(3,4-二羧基苯基)甲烷二酐、雙(3,4-二羧 基苯基)颯二酐(bis(3,4-dicarboxy phenyl)sulf〇ne dianhydride)、3,4,9,10-茈四甲酸二酐(3,4,9,10-perylene tetracarboxylic acid dianhydride)、雙(3,4-二缓基苯基)趟二 酐、苯-1,2,3,4-四甲酸二酐、3,4,3’,4·-二苯甲酮四甲酸二 酐、2,3,2',3’-二苯曱酮四甲酸二酐、3,3,3’,4·-二苯曱酮四甲 酸二酐、1,2,5,6-萘四曱酸二酐、1,4,5,8-萘四甲酸二酐、 2,3,6,7-萘四曱酸二酐、1,2,4,5-萘四甲酸二酐、2,6-二氣萘 201120171jr -1,4,5,8_四曱酸二酐、2,7-二氯萘-1,4,5,8-四曱酸二酐、 2,3,6,7-四氯萘-1,4,5,8-四曱酸二酐、菲-1,8,9,10-四甲酸二 酐、吡嗪-2,3,5,6-四曱酸二酐、噻吩-2,3,5,6-四甲酸二酐、 2,3,3,,4’-聯苯四甲酸二酐、3,4,3,,4,-聯苯四甲酸二酐、 2,3,2’,3'-聯笨四曱酸二酐、雙(3,4-二羧基苯基)二曱基矽烷 二酐、雙(3,4-二羧基苯基)甲基苯基矽烷二酐、雙(3,4-二羧 基苯基)二苯基梦烧二酐、1,4-雙(3,4-二缓基苯基二曱基矽 烷基)苯二酐、1,3-雙(3,4-二羧基苯基)-1,1,3,3-四甲基二環 己烷二酐、對伸苯基雙(偏苯三曱酸酐)、伸乙基四曱酸二 酐、1,2,3,4-丁烷四曱酸二酐、十氫萘-1,4,5,8-四曱酸二酐、 4,8-二甲基-1,2,3,5,6,7-六氫蒽-1,2,5,6-四曱酸二酐、環戊烧 -1,2,3,4-四曱酸二酐、吡咯烷-2,3,4,5-四曱酸二酐、1,2,3,4-環丁烷四曱酸二酐、雙(外-雙環[2,2,1]庚烷-2,3-二甲酸二酐 (bis(exo-bicyclo[2,2,l]heptane-2,3-dicarboxylic acid 出肪1^此(16)、雙環-[2,2,2]-辛-7-烯-2,3,5,6-四曱酸二酐、2,2-雙(3,4-二羧基苯基)丙烷二酐、2,2-雙[4-(3,4-二羧基苯基) 苯基]丙烷二酐、2,2-雙(3,4-二羧基苯基)六氟丙烷二酐、2,2· 雙[4_(3,4-一叛基本基)苯基]六鼠丙烧二軒、4,4’·雙(3 4-二 幾基本氧基)二苯基硫鱗二酐、1,4-雙(2-輕基六敗異丙基) 苯雙(偏苯三曱酸酐)、1,3-雙(2-羥基六I異丙基)苯雙(偏"苯 三曱酸酐)、5-(2,5-二氧代四氫呋喃基)-3-甲基環己稀 -1,2-二甲酸二酐、四氫呋喃_2,3,4,5_四曱酸二酐、下^通式 Ο)所表示的四羧酸二酐等。下述通式(丨)中,a表示2 〜20的整數。 , 45 201120171
上述通式(1)所表示的四竣酸二針例如可由單氣化偏 苯三曱酸酐及對應的二醇來合成,具體可列舉:〖,2·(伸乙 基)雙(偏苯 三甲酸 肝) (l,2-(ethylene)bis(anhyrotrimelitate))、1,3-(三亞甲芙)雔 (偏苯三曱酸酐)、1,4-(四亞曱基)雙(偏苯三甲酸軒)、i 5_(五 亞曱基)雙(偏苯三甲酸酐)、1,6-(六亞曱基)雙(偏苯^甲酸 酐)、1,7-(七亞甲基)雙(偏苯三曱酸酐)、hr亞曱基)雙(偏 苯三曱酸酐)、1,9-(九亞曱基)雙(偏苯三曱酸酐)、^ 1〇 (十 亞曱基)雙(偏苯三曱酸酐)、1,12-(十二亞甲基)雙(偏苯三曱 酸酐)、1,16-(十六亞曱基)雙(偏苯三曱酸酐)、ιΐ8 : 甲基)雙(偏苯三甲酸酐)等。 ’ ’ 另外,四叛1-野就賦予於溶劑中的良好的性及 财濕性、# 365 mn的光的透明性的觀點而古 述通式⑺或通式⑴所絲的 ^雛為下 46 201120171
如上所述的四羧酸二酐可單獨使用一種或組合使用兩 種以上。 被用作上述聚醢亞胺樹脂的原料的其他二胺並無特別 限制’例如可列舉:鄰苯二胺(0_phenylenediamine)、間 笨二胺、對苯二胺、3,3,-二胺基二苯基醚、3,4,-二胺基二 苯基醚、4,4’-二胺基二苯基醚、3,3,_二胺基二苯基甲烷、 3,4’-二胺基二苯基甲烧、4,4’-二胺基二苯基醚曱烷、雙(4· 胺基_3,5_二曱基苯基)曱烷、雙(4_胺基_3,5_二異丙基苯基) 曱烷、3,3'-二胺基二苯基二氟甲烷、3,4,-二胺基二笨基二 氟曱烷、4,4’-二胺基二苯基二氟曱烷、3,3’-二胺基二苯基 *風、3,4’-二胺基二苯基砜、4,养二胺基二笨基砜、3,3’-二胺 基二苯基硫醚、3,4'-二胺基二笨基硫醚、4,4·-二胺基二苯 基硫醚、3,3^二胺基二苯基酮、3,4’-二胺基二苯基酮、4,4’-二胺基二苯基酮、2,2-雙(3-胺基苯基)丙烷、2,243,4’-二胺 基二苯基)丙烷、2,2-雙(4-胺基苯基)丙烷、2,2-雙(3-胺基苯 基)六氟丙烷、2,2-(3,4’-二胺基二苯基)六氟丙烷、2,2-雙(4- 201120171 胺基苯基)六氟丙烧、1,3·雙(3-胺基苯氧基)苯、1,4_雙(3_ 胺基苯氧基)苯、1,4-雙(4-胺基苯氧基)苯、3,3,-(1,4-伸苯基 雙(1-曱基亞乙基))雙苯胺(3,3'_(i,4-phenylenebis(l-methyl ethylidene))bisaniline)、3,4'-(l,4-伸苯基雙(1-曱基亞乙基)) 雙苯胺、4,4·-(1,4-伸苯基雙(i_曱基亞乙基))雙苯胺、2,2· 雙(4-(3-胺基苯氧基)苯基)丙烷、2,2_雙(4_(3胺基苯氧基) 苯基)六氟丙院、2,2-雙(4-(4-胺基苯氧基)苯基)六氟丙烷、 雙(4-(3-胺基工/丰シ)苯基)硫醚、雙(4·(4胺基工^丰シ) 苯基)硫醚、雙(4-(3-胺基工/牛シ)苯基)砜、雙(4_(4_胺基 工/牛シ)苯基)砜、3,3’-二羥基-4,4,-二胺基聯苯、3,5-二胺 基苯曱酸等的芳香族二胺,丨,3_雙(胺基甲基)環己烷、2,2_ 雙(4-胺基苯氧基苯基)丙烷、下述通式(8)所表示的脂肪 族醚二胺、下述通式(9)所表示的矽氧烷二胺等。 上述二胺中’就賦予與其他成分的相溶性的觀點而 言’較佳為下述通式(8)所表示的脂肪族醚二胺,更佳為 乙二醇及/或丙二醇系二胺。下述通式(8)中,R1、R2及 R3分別獨立表示碳數1〜1〇的伸烷基,b表示2〜8〇的整 數。 H2N—R1-^〇—.r2^.〇_R3_NH2 ⑼ 此種脂肪族醚二胺具體可列舉:太陽_工程化學(股)
製造的 JEFFAMINE (商品名)D_23〇、D-400、D-2000、 D-4000、ED-600、ED-900、ED-2000、EDR-148,BASF 48 201120171 (製造)聚_胺 D-230、D-400、D-2000 裳沾 二胺等的脂肪族二胺。該些二胺較佳為所有=伸燒基 耳%以上,就可高度地兼具與其他調配成分^容 及熱壓接性與高溫黏著性的觀點而言,=相洛14、以 以卜。 佳為50莫耳〇/〇 另外 上逃-祕附室溫下的密接性 點而言,較佳為下述通式⑼所表示的 2 = 通式⑼中,R1R9分別獨立表示碳數Μ—二= 或可具有取代基的伸苯基,R5、R6、R7及R8分 ^ 不碳數1〜5的絲、苯基或苯氧基,d表示卜5的整數。
R7 〇~Si- I R8
⑼ 該些二胺較佳為設定為所有二胺的〇5莫耳%〜8〇 莫耳%,就可高度地兼具熱壓接性與高溫黏著性的觀點而 。,更佳為设定為1莫耳%〜50莫耳%。若低於〇 5莫耳 /〇,則添加石夕氧烧二胺的效果變小,若超過8〇莫耳%,則 有與其他成分的相溶性、高溫黏著性下降的傾向。 關於上述通式(9)所表示的矽氧烷二胺,具體而言, 式(9)中的d為1的矽氧烷二胺可列舉ι,ι,3,3-四曱基-1,3-雙 (4- 胺基笨基)二砍氧烧 (l,l,3,3-tetramethyl-l,3-bis(4-aminophenyl)disiloxane )、 49 201120171 1,1,3,3-四苯氧基-l,3_雙(4_胺基乙基)二矽氧烷、mg, 苯基-ι,3-雙(2-胺基乙基)二矽氧烷、m3四苯基‘以雙 (3-胺基丙基)二矽氧烷、四曱基·13_雙(2_胺基乙基) 二石夕氧烧、U,3,3-四曱基_1,3_雙(3-胺基丙基)二矽氧烷、 l1,3,3-四曱基-U-雙(3-胺基丁基)二矽氧烷、1,3_二曱基 -1,3·二甲氧基·1,3·雙(4-胺基丁基)二矽氧烷等,d為2的矽 氧烧二胺可列舉:1,1,3,3,5,5-六曱基-1,5-雙(4-胺基苯基)三 妙氧烧(l,l,3,3,5,5-hexamethyl-l,5-bis(4-aminophenyl) trisiloxane)、l,l,5,5·四苯基_3,3-二曱基-1,5-雙(3-胺基丙基) 二矽氧烷、1,1,5,5-四苯基-3,3-二曱氧基-1,5-雙(4-胺基丁基) 三矽氧烷、1,1,5,5·四苯基_3,3_二曱氧基_1,5-雙(5-胺基戊基) ,矽氧烷、1,1,5,5-四甲基_3,3_二甲氧基-1,5_雙(2_胺基乙基) f矽氧烷、1,1,5,5-四甲基_3,3_二曱氧基-1,5-雙(4-胺基丁基) ^石夕氧燒、1,1,5,5-四甲基-3,3-二曱氧基-1,5_雙(5_胺基戊基) 三矽氧烷、1,1,3,3,5,5-六甲基-1,5-雙(3-胺基丙基)三矽氧 燒、U,3,3,5,5-六乙基-l,5-雙(3-胺基丙基)三矽氧烷、 1’1,3,3,5,5-六丙基],5_雙(3_胺基丙基)三矽氧烷等。 上述二胺可單獨使用一種或組合使用兩種以上。 上述聚酿亞胺樹脂可單獨使用一種或視需要將兩種以 上混合(摻合)使用。 於決疋聚醯亞胺樹脂的組成時,較佳為將其Tg設計 為150°C以下。作為聚醯亞胺樹脂的原料的二胺特佳為使 用上述通式(8)所表示的脂肪族醚二胺。 於上述聚醯亞胺樹脂的合成時,藉由將下述通式 50 201120171 (10)、通式Οι)或通式(12)所表示的化合物之類的單 官能酸酐及/或單官能胺投入至縮合反應液中’可於聚合物 末端導入酸酐或二胺以外的官能基。另外,藉此可降低聚 合物的分子量’降低黏著劑樹脂組成物的黏度,提高熱壓 接性。
熱硬化性樹脂亦可於其主鏈及/或支鏈中含有具有促 進環氧樹脂的硬化的功能的咪唑基等的官能基。例如,含 有咪唑基的聚醯亞胺樹脂例如可藉由使用下述化學式所表 示的含有咪唑基的二胺作為用於合成聚醯亞胺樹脂的一部 分一胺的方法而獲得。 201120171
上述聚醯亞胺樹脂就可均白 言,較佳為成形為3G师的^ t B-階段化的觀點而 Α ΐΛο/ ,. , ^ 膜异時的對365 nm的透射率 為10/❶以上,就於更低的曝光量 耵旱 以上。此種聚醯亞:== 通式(2)所表示的酸酐、與上述通式⑻所表示的 月曰肪細二胺及/或上賴式⑼所表示⑽紐 應而合成。 久 熱塑性樹脂就抑制黏度上升、進而減少黏著劑組成物 中的溶解殘餘物的觀點而言,較佳為使用在常溫(25。〇 下為液狀的熱塑性樹脂。藉由使用此種熱塑性樹脂,可於 不使用溶劑的情況下進行加熱而反應,對於實質上不含溶 52 201120171 劑的黏著劑組成物而言,於削減溶劑去除的步驟、減少歹、 存溶劑、削減再沈澱步驟的方面有用。另外,液狀熱 樹脂亦容易自反應爐中取出。此種液狀熱塑性樹脂 別限定,可列舉聚丁二烯、丙烯腈-丁二烯低聚物、聚&戊 二烯、聚丁烯等的橡膠狀聚合物,聚烯烴,丙烯酸系聚2 物,聚矽氧聚合物,聚胺基曱酸酯,聚醯亞胺,聚醯胺^ 亞胺等。其中可較佳地使用聚醯亞胺樹脂。 液狀的聚醯亞胺樹脂例如是藉由使上述酸針與脂肪族 醚二胺或矽氧烷二胺反應而獲得。關於合成方法,可藉= 不添加溶劑而使酸酐分散於脂肪族醚二胺或矽氧烧二^中 並進行加熱而獲得。 本實施形態的黏著劑組成物視需要亦可含有增感劑。 該增感劑例如可列舉:樟腦醌(camph〇roquinone )、苯偶 醯、二乙醯(diacetyl)、苯偶醯二甲基縮酮、苯偶醯二乙 基縮酮、本偶酿二(2-曱氧基乙基)縮酮、4,4·-二曱基苯偶酿 -一曱基縮酮、蒽自昆、1-氣蒽醌、2-氣蒽酿、1,2-苯幷蒽酿、 1- 經基蒽酿^、1-甲基蒽g昆、2-乙基蒽酿、1-漠蒽酿(、n塞領酉同、 2- 異丙基噻噸酮、2-硝基噻噸酮、2-甲基噻噸酮、2,4-二甲 基噻噸酮、2,4-二乙基噻噸酮、2,4-二異丙基噻噸酮、2-氣 -7-二氟甲基嘆嘲g同、β塞η頓__1〇,1〇_二氧化物、嗟嘲酮_1〇_ 氧化物、安息香曱_ ( benzoin methylether)、安息香乙_、 異丙醚、安息香異丁醚、二苯曱酮、雙(4-二曱胺基苯基) 酮、4,4’-雙二乙基胺基二苯甲酮、含有疊氮基的化合物等。 該等可單獨使用或併用兩種以上。 53 201120171 本貫施形態的黏著劑組成物視需要亦可含有熱自由基 產生劑。熱自由基產生劑較佳為有機過氧化物。有機過氧 化物較佳為1分鐘半衰期溫度為8〇〇c以上的化合物,更佳 為100 C以上,最佳4 12(TC以上。有機過氧化物是考慮到 黏著劑組成物的製備條件、成膜溫度、硬化(貼合)條件、 其他製程條件、儲存穩定性等而選擇。可使用的過氧化物 並無特別限定’例如可列舉:2,5_二曱基_2,5_二(第三丁基 C^5-dimethyl-2,5-di(t-butylperoxy hexane)), 過氧化二異丙苯(dieumyl p⑽過氧化·2·乙基己酸 第三丁醋(t-butyl-peroxy_2_ethyl hexanate)、過氧化_2_乙 基己酸第三己S旨、i,:U雙(第三丁基過氧化)_3,3,5_三甲基環 己烧、1,1·雙(第三己基過氧化)_3,3,5_三曱基環己烧、過氧 化一碳酸雙(4-第二丁基環已基)g旨等,可單獨使用其中一 種或混合㈣兩種以上。藉由含有有機過氧化物,可使曝 光時殘存的未反應的放射_合性化合物反應,可實現低 逸氣化、南黏著化。 熱自由基產生劑的添加量相對於放射線聚合性聚合化 合物的總量較佳為_質量%〜2G質量%,更佳為^質 量%〜10質里%’最佳為0.5質量%〜5質量%。若為⑽ 質量%以下,則有硬化性下降,其添加效果變小的傾向, 若超過5龍%,财逸氣量增加,或保存穩定性下降的 傾向。 熱自由基產生劑較佳為半衰期溫度為贼以上的化 合物。例如可列舉:Perhexa (商〇口口名)25B (日油公司製 54 201120171jr 造)、2,5-二甲基_2,5·二(第三丁基過氧化己烧)(j分鐘半衰 期溫度:180°〇’ρ6πηΗηγ1(商品名)D(曰油公司製造)、 過氧化一異丙笨(1分鐘半衰期溫度:175〇C )等。 本實施形態的黏著劑組成物中,為了賦予保存穩定 性、製程適應性或抗氧化性,亦可於無損硬化性的範圍内 更添加酿類、多元_、苯_、亞磷酸醋類、硫類等的 聚合抑制劑或抗氧化劑。 黏著触絲巾亦可適#含魏料。填料例如可列 ^二銀粉、金粉、銅粉、鎮粉、錫等的金屬填料,氧化銘、 =匕I氫氧化鎂、碳_、碳酸鎂、賴^石夕酸鎮、 曰w ^化鎂、减銘、氮化紹、結晶性二氧化石夕、# ί氧化鈦、玻璃、氧化鐵、陶篆 類.幵m o 橡㈣填料等的有機填料等,無論種 類減等如何,可無特別限制地使用。 上,填料可根據所需功能而區 =樹脂組成物賦予導電性、導】真 的而添加’非金屬無機填 u生寺為 等為目^」 易剝離性)、低熱膨脹性、低吸满性 添加,有機填料是以對黏著劑㈣性等為 =些金屬填料、無機填 或組合使用兩種以上。盆士 ^ 付」早獨使用一種 材料所需求的導電性、導餘賦予半導體裝置用黏著 觀點而言,較性、低吸婦性、絕緣性等的 較佳為金屬填料、錢填料 55 201120171 無機填料統雜養巾,織樹脂清漆㈣分散性良好 二可賦予熱時的高黏著力的觀點而言,更佳為二氧化石夕填 上述填料較佳為平均粒徑為1〇师以下、且最大粒徑 二μιη以下’更佳為平均粒徑為5叫以下、且最 輕為20 μιη以下。苦早於粉你扣t ;' 右十々粒仫超過10 μιη、且最大粒徑超 二μιη則有無法充分獲得破_性提昇效果的。 =卜’料粒徑及最妹㈣下限絲_限制, 兩 U.U01 μηχ。 相料ΐΐ填料的含量是根據钱予的雜或魏而決定, 二對於樹脂成分與填料的合計量較料G f量%〜5〇 里/。,更佳為1質量%〜40質量%,進而佳為 3〇質量%。藉由增加填料的量,實 ^ 0 j貫現低α化、低吸濕化 二提昇切割性(使用切割刀的切斷性), 丁線^性(超音波效率)、熱時的黏著強度。 若使填料增加至必要量以上,則有黏戶上 接性受損的傾向,故較佳為將埴 二升或熱屋 Ϊ。的特性的平衡,而決定最適的填料含 :耗=混合•混練可將通常的_機、石磨機、 —親磨f、球磨機等的分散機適當組合來進行。 好,:if物中’為了使不同種材料間的界面結合變 寻y、中就效果向的方面而言,較佳A功、μ 合劑’更佳為具有環氧基等的熱硬化性基或甲=: 56 201120171 及/或丙稀酸i旨等的放射線聚合性基的化合物。另外,上述 石夕烧系偶合劑的沸點及/或分解溫度較佳為l5〇°c以上,更 佳為180°C以上,進而佳為2〇〇〇C以上。即,最佳為使用 200°C以上的沸點及/或分解溫度、且具有環氧基等的熱硬 化性基或曱基丙稀酸酯及/或丙烯酸酯等的放射線聚合性 基的矽烷系偶合劑。上述偶合劑的使用量就其效果或耐熱 性及成本的方面而言,較佳為相對於所使用的所有樹脂組 成物100質量份而設定為〇 01質量份〜20質量份。 黏著劑組成物中,為了吸附離子性雜質而使吸濕時的 絕緣可靠性變好,亦可更添加離子捕獲劑。此種離子捕獲 劑並無特別限制,例如可列舉:三嗪硫醇化合物、酚系還 原劑等的作為用以防止銅變為離子溶出的銅毒抑制劑而已 知的化合物,粉末狀的絲系、録系、鎮系、銘系、鍅系、 辦系鈦系、錫系及該些的混合系等的無機化合物。具體 ,並無特·定’有東亞合成⑻製造的無機離子麵 劑’商品名 IXE·300 (録系、)、IXE-500 (紐幻、IXE_6〇〇 /(錄、城合系)、ΙΧΕ_·(镁、減合系)、咖-麵(錯 糸ΙΧΕ 11〇〇 (!弓系)等。該些離子捕獲劑可單獨使用或 用兩種以上。上述離子捕獲劑的使用量就添加效果 二本等的觀點而言,相對於所有樹脂組成物100 質里伤較佳為〇 〇1質量份〜1〇質量份。 [實例] 以下,列舉實例對本發明加以更具體說 不限定於該些實例。 仁本^月 57 201120171 <熱塑性樹脂(聚醯亞胺樹脂)> (PM) 於具備攪拌機、溫度計及氮氣置換裴置的燒瓶内,添 加5,5’-亞甲基雙(鄰胺基苯甲酸)(]^八八)5 72 8(〇〇2莫 耳)、脂肪族醚二胺(商品名「D-400」)13 57 g (〇〇3莫 耳)、1,1,3,3-四曱基雙(3-胺基丙基)二石夕氧烧(商品名 「BY16-871EG」,東麗道康寧(股)製造)2 48 g (〇 〇1莫 耳)、及1,4-丁二醇雙(3-胺基丙基)喊(商品名「B12」,東 京化成工業股份有限公司製造,分子量^ 莫耳)、及作為溶劑的NMP 110 g,進行攪拌,使該些二胺 溶解於溶劑中。 一 邊將上述燒瓶於冰洛中冷卻,一邊於燒瓶内的溶液 中逐次少量添加4,4’-氧代雙鄰苯二甲酸二野(〇DpA)29 % g (0.09莫耳)及偏苯三曱酸軒(TAA) 3.84 g (〇.〇2莫 耳)。添加結束後,於室溫下擾拌5小時。其後,於燒瓶中 安裝附有水分接受器的回流冷凝器,添加二曱苯7〇 5 g, 邊吹入氮氣一邊使>谷液升溫至18〇°C並保溫5小時,將 二曱苯與水一起共沸去除,獲得聚醯亞胺樹脂的清 漆《對聚醯亞胺樹脂PI-1進行凝膠滲透層析儀(Gel
Permeation Chromatography,GPC)測定,結果以標準聚 本乙烯換算的重量平均分子量(Mw)為21000。另外,聚 醯亞胺樹脂PI-1的Tg為55°C。 進行3次使用所得的聚醯亞胺樹脂丨的清漆的利用 純水的再沈澱純化,使用真空烘箱於6〇。〇加熱乾燥3天, 58 201120171 獲得聚醯亞胺樹脂Ι>1-1的固形物。 (PI-2 ) 於具備攪拌機、溫度計及氮氣置換裝置(氮氣流入管) 的500mL燒瓶内,於聚氧伸丙基二胺(商品名「D-2000」’ 分子量為約2〇00’ BASF製造)140 g( 0,07莫耳)、及1,1,3,3-四曱基-1,3-雙(3-胺基丙基)二石夕氧炫·(商品名 「BY16-871EG」,東麗道康寧(股)製造)3.72g(〇.〇15莫 耳)中’將ODPA 31.0 g (〇·ι莫耳)逐次少量添加至燒瓶 内的溶液中。添加結束後,於室溫下攪拌5小時。其後, 於燒瓶中安裝附有水分接受器的回流冷凝器’一邊吹入氮 氣一邊使溶液升溫至180。(:並保溫5小時而去除水’獲得 液狀的聚醯亞胺樹脂1>1-2。對聚醯亞胺樹脂Π-2進行GPC 測定,結果以標準聚苯乙烯換算計重量平均分子量(Mw) 為40000 »另外,聚醯亞胺樹脂pi-2的Tg為20°C以下。 (PI-3 ) 於具備攪拌機、溫度計及氮氣置換裝置(氮氣流入管) 的500 mL燒瓶内,於聚氧伸丙基二胺(商品名「D-2000」, 分子量為約2〇0〇,BASF製造)l〇〇g(〇.〇5莫耳)、及1,1,3,3-四曱基-1,3-雙(3-胺基丙基)二矽氧烷(商品名 「BY16-871EG」,東麗道康寧(股)製造)3.72g(0.015莫 耳)、2,4-二胺基-6-[2·-十一烷基咪唑基(1’)]乙基-均三嗪(商 品名「C11Z-A」,四國化成(股)製造)7.18 g (〇.〇2莫 耳)中,將ODPA31.0g (0.1莫耳)逐次少量添加至燒瓶 内的溶液中。添加結束後,於室溫下攪拌5小時。其後, 59 201120171 於燒瓶中安裝附有水分接受器的回流冷凝器,一邊吹入氮 氣一邊使溶液升溫至l80°c並保溫5小時而去除水,獲得 液狀的聚醯亞胺樹脂PI-3。對聚醯亞胺樹脂PI-3進行GPC 測定’結果以標準聚苯乙烯換算計重量平均分子量(Mw) 為40000。另外,聚醯亞胺樹脂PI-3的Tg為20〇C以下。 黏著劑組成物的製備 使用上述所得的聚醯亞胺樹脂PI-1、聚醯亞胺樹脂 Π-2及聚醯亞胺樹脂ρι_3,以下述表1所示的組成比(單 位:質量份)調配各成分’獲得實例1〜實例8及比較例i 〜比較例6的黏著劑組成物。 表1中,各記號是指下述物質。 (熱硬化性樹脂) •YDF-8170C:東都化成公司製造,雙酚F型雙縮水甘 油醚(5%重量減少溫度:27〇〇C,黏度:1300 mPa.s) •63GLSD :日本環氧樹脂公司製造,縮水甘油胺型環 氧樹脂(5%重量減少溫度:24(TC,黏度:600mPa.s) (放射線聚合性化合物) •A-BPE4 :新中村化學工業公司製造,乙氧基化雙酚 A型丙烯酸酯(5%重量減少溫度:33(TC,黏度:980 mPa.s) •M-140:東亞合成公司製造,丙烯酸_2-(l,2-環己羧基 醯亞胺)乙酯(5%重量減少溫度:20(TC,黏度:450 mPa.s ) •AMP-20GY:新中村化學工業公司製造,苯氧基二乙 二醇丙烯酸酯(5%重量減少溫度:175t,黏度:16mPa*s) (硬化促進劑) 201120171
- ---JT -I •2PZCNS-PW:四國化成公司製造,1-氰乙基-2-苯基 咪唑鏽偏苯三曱酸鹽(5%重量減少溫度:220°C,平均粒 徑:約4 μιη ) (光起始劑) •1-651 : Ciba Japan 公司製造,2,2-二曱氧基-1,2-二苯 基乙烷-1-酮(5%重量減少温度:170°C,i射線吸光係數: 400 ml/gcm) (熱自由基產生劑) •Percumyl D :日油公司製造,過氧化二異丙苯(1分 鐘半衰期溫度:175°C) (塗佈溶劑) •NMP :關東化學公司製造,N-甲基-2-吡咯烷酮 61 201120171 [表l]
黏著劑組成物的5%重量減少溫度(曝光後) 藉由旋塗(2000 ipm/l〇 s、4〇〇〇 rpm/2〇 s)將 組成物塗佈於矽晶圓上,對所得的塗膜層壓經脫模處== PET膜,藉由高精度平行曝光機(〇RC製作所製造,' EXM-1172-B-oo」(商品名))以1〇〇〇 mJ/cm2進行曝光。 對曝光後的黏著劑組成物使用熱重/熱示差同步分析儀 (SII奈米技術公司製造’商品名「TG/DTA6300」)於升 62
201120171 -.…f』I 溫速度KTC/min、氮氣流(400ml/min)的條件下測定5% 重量減少溫度。 ° 黏著劑組成物的5%重量減少溫度(硬化後) 將與上述方法同樣地獲得的曝光後的黏著劑組成物於 烘箱中於120〇C加熱1小時、繼而於180〇c加熱3小時,藉 此使其硬化,對所得的硬化後的黏著劑組成物於與上述相 同的條件下測定5%重量減少溫度。 ^ 黏度 使用東京計器製造所製造的EHD型旋轉黏度計對黏 著劑組成物的於25°C的黏度進行測定。 膜厚 藉由旋塗(2000 rpm/10 s、4000 ipm/20 s)將黏著劑 組成物塗佈於矽晶圓上,對所得的塗膜(黏著劑層)層壓 經脫模處理的PET膜,藉由高精度平行曝光機(〇RC製 作所製造,「EXM-1172-B-oo」(商品名))以 1〇0〇 mJ/cm2 進行曝光。其後,使用表面粗糙度測定器(小阪研究所製 造)對黏著劑層的膜厚進行測定。 熱壓接性(剪切黏著強度) 藉由旋塗(2000 rpm/10 s、4000 rpm/20 s)將黏著劑 組成物塗佈於矽晶圓上,對所得的塗膜層壓經脫模處理的 PET膜’藉由高精度平行曝光機(〇RC製作所製造, 「EXM-1172-B-oo」(商品名))以 1〇〇〇 mJ/cm2 進行曝光。 其後’自石夕晶圓切出3 mm><3 mm見方的石夕晶片。將所切 出的附黏者劑層的碎晶片載置於預先準備的5 rnm><5 mm 63 201120171 w -pit =方的♦“上’-邊以UK) gf加壓,一邊加熱至i2〇t 並且壓接2秒鐘。其後,於供箱中於i2(rc加熱!小 繼而於丨随加熱3小時,獲得以片彼絲著的樣品。 對所得的樣品使用剪娜著力試驗機「Dage 4_」(商品 名)測定於室溫及於260°C的剪切黏著力。將所得的測定 值作為剪切黏著強度的值。 黏著強度(表面黏力) 藉由旋塗(2000 rpm/10 s、4〇〇〇 rpm/2〇 s)將黏著劑 組成物塗佈於矽晶圓上,對所得的塗膜(黏著劑層)層壓 經脫模處理的PET膜,藉由高精度平行曝光機(〇Rc製 作所製造,「EXM-im-B-cx»」(商品名))以1000 mJ/cm2 進行曝光。其後,使用Rhesca公司製造的探針黏性試驗 機,於探針直徑為5.1 mm、剝取速度為10 mm/s、接觸荷 重為100 gf/cm2、接觸時間為1 s的條件下,測定於30。〇 及於120°C的黏著劑層表面的黏力。 64 201120171 [表2] 實例 ~-- 1 2 3 6 7 8 黏度(mPa,s) 800 550 1200 200 650 800 500 膜厚(μηι) 7 5 10 2 6 ------ 5 (jw 7 曝光 5%重量減少 後 250 240 260 180 250 240 240 220 溫度(°C) 熱硬 ~-- 化後 360 350 380 260 360 350 350 300 表面黏力 30°C 10 — 40 3 50 30 30 20 J〇 (gf/cm2 ) 120°C 250 400 200 >500 400 400 350 350 剪切黏著強 25〇C >10 >10 >10 8 7 >10— >10 >l〇 度(MPa) 260〇C 1.4 1.0 1.2 0.30 0.20 0.35 0.70 — 0.70 比J 陵例 ~~ 1 2 3 4 p — 5 6 Q^n 黏度(mPa-s) 150 100 1000 1000 650 膜厚(μηι) 2 2 10 9 5 1 9 240 5%重量減少溫度(°C) 曝光後 <150 <150 280 280 16〇| 熱硬化後 - - 350 350 260 >5〇〇 260 25 250 2.5 表面黏力(gf^cm2) 30°C 280 >500 1.2 1.5 120%i >500 >500 1.5 1.8 > son 剪切黏著強度(MPa) 25〇C 260°Γ 剝離 剝離 專||雜 0.5 剝離 ^yj\j 羽雕 ^O.lu 制離 剝離 <0.10 二===::本·保護 【圖式簡單說明】 … 圖1是表 意圖 示半導體裝置的製造方法的一實施形態的示 65 201120171 圖2是表示半導體裝置的製造方法的一實施形態的示 意圖。 圖3是表示半導體裝置的製造方法的一實施形態的示 意圖。 圖4是表示半導體裝置的製造方法的一實施形態的示 意圖。 圖5是表示半導體裝置的製造方法的一實施形態的示 意圖。 圖6是表示半導體裝置的製造方法的一實施形態的示 意圖。 圖7是表示半導體裝置的製造方法的一實施形態的示 意圖。 圖8是表示半導體裝置的製造方法的一實施形態的示 意圖。 圖9是表示半導體裝置的製造方法的一實施形態的示 意圖。 圖10是表示半導體裝置的製造方法的一實施形態的 示意圖。 圖11是表示半導體裝置的製造方法的一實施形態的 示意圖。 圖12是表示半導體裝置的製造方法的一實施形態的 示意圖。 【主要元件符號說明】 1 :半導體晶圓 66 201120171
V y 〆卜^乂 JL 2:半導體晶片 4:膠帶(背面研磨膠帶) 5 :黏著劑組成物(黏著劑層) 6:膠帶(切割膠帶) 7:支撐部件 8:研磨裝置 9 :曝光裝置 10 ·晶圓壞 11 :切割刀 12 :固晶裝置 14 :熱盤 16 :導線 17 :密封材 20 :箱 21 :夾具 100 :半導體裝置 D :切割線 51 :半導體晶圓的電路面 52 :半導體晶圓的背面 67
Claims (1)
- 201120171 七、申請專利範園: L -難著齡錢,含魏射料合性化合物、光 起始劑及熱硬化性樹脂,用於黏著半導體晶片並且 藉由光照射卿録著歸的上述成物進行 了 B-階段化時,上述黏著綱表面的黏力於3叱為細 gf/cm 以下,於 12〇t 為 2〇〇 gf/cm2 以上。 /·如申請專職㈣丨項所述之轉敝成物,其藉 由光照射進行了 B,段化時的w重量減少溫度為⑼ 以上。 3.如申請專利範圍第丨項所述之黏著劑組成物,其藉 由光照射進行3_階段化前的於25〇c的黏度為1〇 mpa·^^ 30000 mPa.s。 * 4.如申請專利範圍第丨項所述之黏著劑組成物,其中 於藉由上述黏著劑組成物將半導體晶片黏著於被黏著體 時,上述半導體晶片與上述被黏著體的剪切黏著強度於 260°C為 0.2MPa 以上。 又、 5. 如申請專利範圍第1項所述之黏著劑組成物,其藉 由光照射進行B-階段化後,進一步藉由加熱而硬化時的 5%重量減少溫度為260°C以上。 6. 如申請專利範圍第1項所述之黏著劑組成物,其中 上述放射線聚合性化合物包含單官能(甲基)丙烯酸酯。 7. 如申請專利範圍第1項所述之黏著劑組成物,其包 含具有醯亞胺基的化合物。 8·如申請專利範圍第6項所述之黏著劑組成物,其中 68 201120171 Γ 上述單宫能基)丙烯酸酯包含具有醯亞胺基的基 婦酸s旨。 Α 9.二種半導體裝置的製造方法,包括以下步驟: 於半導體晶圓的背面上塗佈如申請專利範圍第1項至 第8項中任一項所述之黏著劑組成物的步驟; 藉由光照射使所塗佈的上_著齡成物進行 段化的步驟; & 物半導體晶圓與經B_階段化的上述黏著劑組成 物起切斷,切分成多個半導體晶片的步驟;以及 件之組成物夾持於上述半導體晶片與支撐部 二或上述半導體晶片與其他半導體晶片之間並進行廢 接,藉此加以黏著的步驟。 瓜-種半導體農置,其可藉由如申請專利範圍第9 項所述之製造方法而獲得。 69
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