TW570966B - A curable adhesive composition for use in microelectronic devices - Google Patents

A curable adhesive composition for use in microelectronic devices Download PDF

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Publication number
TW570966B
TW570966B TW090108606A TW90108606A TW570966B TW 570966 B TW570966 B TW 570966B TW 090108606 A TW090108606 A TW 090108606A TW 90108606 A TW90108606 A TW 90108606A TW 570966 B TW570966 B TW 570966B
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Taiwan
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carbon atoms
independently
alkyl group
cis
group
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TW090108606A
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English (en)
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Donald E Herr
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Nat Starch Chem Invest
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    • C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
    • C09J183/10—Block or graft copolymers containing polysiloxane sequences
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    • C09J179/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09J161/00 - C09J177/00
    • C09J179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C09J179/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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    • C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
    • C08F283/04—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polycarbonamides, polyesteramides or polyimides
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Description

經濟部智慧財產局員工消費合作社印製 570966 A7 一 B7 五、發明說明（i) 本案爲1999年六月18日提出之第09/336,245號案之部 份繼續申請案〇 本發明領域 本發明有關適合用作微電子元件或半導體封裝黏著劑 之組合物〇 本發明背景 黏著劑組合物，尤其導電性黏著劑，係在半導體封裝 及微電子元件之製作及組裝中用於各種目的〇較突顯之用 法爲將積體電路晶片黏合於引線框或其他基質，及將電路 封裝或總成黏合於印刷線路板〇 對電子包裝作業中導電性黏著劑之要求爲其等須具有 良好之機械强度、不影響組件或載體之固化性質、及與目 前工業中所用現有塗施設備相容之觸變性質〇 黏著劑黏合或交連技藝之另一重要情況爲黏接頭再加 工之能力〇對於涉及大體積物品之單一晶片包裝作業而言 ，可將故障之晶片丟棄而無顯著損失◦然而，丟棄僅有一 故障晶片之複晶片封裝則屬昂貴；準此，故障晶片再加工 之能力將爲製作上之優點0現今，半導體工業之一主要推 力爲開發各種符合所有黏著劑强度及撓性要求，但亦可再 加工之黏著劑，亦即將能予移除而不破壞基質。 本發明綜述 本發明有關一種用於電子裝置之黏著劑組合物，包含 一或更多單或多官能順丁烯二醯亞胺化合物或者一或更多 順丁烯二醯亞胺化合物以外之單或多官能乙烯基化合物或 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297 (請先閱讀背面之注意事項再填寫本頁) ，-裝------r-ltr---------一 570966 A7 137 五、發明說明（2) 者順丁烯二醯亞胺與乙烯基化合物之組合、一固化起發劑 、及隨意之一或更多填料之可固化組合物〇該組合物係設 計成可再加工〇 在另一具體形式中，本發明爲該由上述可固化黏著劑 組合物產生之固化黏著劑0 在另一具體形式中，本發明爲一種微電子總成，包含 一用一固化黏著劑組合物黏合於基質之電子組件，該組合 物係由一包含一或更多單或多官能順丁烯二醯亞胺化合物 或者一或更多單或多官能乙烯基化合物或者順丁烯二醯亞 胺與乙烯基化合物之組合、一固化起發劑、及隨意之一或 更多填料之組合物所製備〇 本發明詳诚 用於本發明黏著劑組合物中之順丁烯二醯亞胺及乙烯 基化合物乃可固化之化合物，意指其等能進行聚合反應， 不論有無交聯。如說明書中所用，固化意指進行聚合，不 論有無交聯〇如業界所了解，交聯作用爲二聚合物鏈藉一 元素、分子基團、或化合物之橋接而附著，且一般而言在 加熱時發生。當交聯密度增加時，物質性質可由熱塑性改 變至熱固性〇 藉由單或多官能化合物之正確選擇及用量有可能製備 寬廣交聯密度範圍之聚合物Q多官能化合物之反應部份愈 大，交聯密度愈大。若需要熱塑化性質，該等黏著劑組合 物可由單官能化合物製備以限制交聯密度〇可添加小量之 多官能化合物以對該組合物提供一些交聯作用及强度，唯 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297 (請先閱讀背面之注意事項再填寫本頁) 裝 訂： 經濟部智慧財產局員工消費合作社印製 570966 A7 __B7 ____ 五、發明說明（3) 多官能化合物之量限制於不使所需熱塑化性質消失之量0 在此等參數內，個別黏著劑之强度及彈性可裁修以適應特 定之最終用途0 在必需將該總成再加工及使用熱塑性物質之情況下， 電子組件可予撬離基質，並可將任何殘餘黏著劑加熱直到 其軟化而易移除爲止〇 交聯密度亦可加以控制，以給予該已固化黏著劑一寬 廣範圍之玻璃轉變溫度，以承當後續之處理及操作溫度〇 在本發明黏著劑組合物中，順丁烯二醯亞胺及乙烯基 化合物可單獨或組合使用。該順丁烯二醯亞胺或乙烯基化 合物或二者在可固化封裝黏著劑組合物內之存在量，以存 在之有機成份（不含任何填料）爲準爲2至98重量％ 〇 該黏著劑組合物進一步包含至少一自由基起發劑，其 定義爲一種分解成具有一或更多未配對電子、高度反應且 通常壽命短之分子片段之化學物種，能藉由鏈機制起發化 學反應〇該自由基起發劑存在量爲該等有機化合物（不含 任何填料）重量之〇·1至10%，較佳爲ϋ·1至3.0 % 〇該 經濟部智慧財產局員工消費合作社印製 -------------裳·-- (請先閱讀背面之注意事項再填寫本頁) .% 自由基固化機制提供迅速之固化，並對該組合物提供固化 前之長架儲壽命〇較佳之自由基起發劑包括過氧化物譬如 過辛酸丁酯及過氧化雙異丙苯以及偶氮化合物譬如2,2，-偶氮雙（2 -甲基丙腈）及2,2’-偶氮雙（2_甲基丁腈）〇 另法，各黏著劑組合物可含有光起發劑以取代自由基 起發劑’然後可藉紫外線照射起發固化程序〇光起發劑之 存在量爲該等有機化合物（不含任何填料）之重量之0.1 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公_ ) ""' 570966 A7 137 經濟部智慧財產局員工消費合作社印製 五、發明說明（4) 至1 0 %，較佳爲〇 · 1至3 · 0 % 0有些情況下，光起發及熱 起發二者可能均皆合宜。舉例言之，固化程序可藉紫外線 照射起始，而在稍後之處理步驟中，可藉加熱完成自由基 固化而完成固化作用0 一般而言，此等組合物將在80-2 0 0 °C之溫度範圍內固 化，而固化作用將在少於1至60分鐘之時間長度內完成。 如一般所了解，每一黏著劑組合物之時間及溫度態樣均有 變化，故可設計不同之組合物以提供適合特定工業製作程 序之固化態樣〇 合宜之黏著劑用導電性填料爲銀、銅、金、鈀、鉑。 於某些情況成，可能需要非導電性填料以例如調節流變性 ，譬如明礬、矽石、及鐵佛龍〇 如說明書通篇所用，符號C ( 0 )係指羰基團〇 順丁烯二醯亞胺化合物 適用於本發明黏著劑組合物之順丁烯二醯亞胺化合物 具有一由通式[M-Xm]n-Q或通式[M-Zm]n-K所代表之結構 〇對於此等特定通式，當小寫爲整數1時，該化合物 將爲一單官能化合物；而當小寫"η ”爲整數2至6時，該 化合物將爲一多官能化合物〇 在通式[M-Xm]n-Q代表之化合物中： Μ爲具有下列結構式之順丁烯二醯亞胺部份：
本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公 (請先閱讀背面之注意事項再填寫本頁) 裝 ---1 I 訂*--------- % 570966 A7 B7 五、發明說明（5) 式中R1爲Η或L至C5烷基； 每一 X獨立爲一由具有下列結構式（ί )至（IV )之芳香 族基團中選出之芳香族基團： 0) (II) (III)
(IV) ——C—ΝΗ— Q爲線性或有支鏈烷基、烷基氧基、烯烴、烯氧基、 芳基、芳基氧基、院胺、院硫化物、稀肢、嫌硫化物、或 芳基硫化物等物種，可含有自該鏈懸垂或作爲該鏈部份主 幹之飽和或不飽和環狀或雜環狀取代基，且其中存在之任 何雜原子可能或可能不直接附接於X ; 或者Q爲具有下列結構之胺基甲酸乙酯： ;. 〇 0 0 0 —R2 一X一C—NH一(〇，#一0—S一NH“R3-NH廉? 式中R2獨立爲一具有1至18個碳原子之烷基、芳基、或芳 基烷基；R3爲一在鏈內有高至100個原子之烷基或烷基氧 基鏈，該鏈可含有芳基取代基；X爲〇、S、N或P ;而7 爲〇至50 ; 或者Q爲具有下列結構式之酯： 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297 (請先閱讀背面之注意事項再填寫本頁) 裝---------- 訂------ 經濟部智慧財產局員工消費合作社印製 570966 Α7 ______ Β7 五、發明說明（6) 〇 0 一C一 〇—R3一〇— 中一 式中R3爲一在鏈內有高至100個原子之烷基或烷基氧基鏈 ，該鏈可含有芳基取代基； 或者Q爲具有下列結構式之矽氧烷·· -(CR^je-tSiR^Olr-SiRS-CCR^ig-式中每一位置之R1取代基獨立爲Η或一具有1至5個碳原 子之烷基團，且每一位置之R4取代基獨立爲Η 、一具有1 至5個碳原子之烷基團、或一芳基團，而e及g獨立爲1 至1〇且f爲1至50 ;而 m爲〇或1 ，且η爲1至6〇 較佳之組合物爲脂肪族雙順丁烯二醯亞胺化合物類， 其中順丁烯二醯亞胺部份係經由胺基甲酸乙酯或尿素鍵合 連接於該主幹，譬如在下列較佳化合物中者： (請先閱讀背面之注意事項再填寫本頁) 裝 訂·
本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公 570966 A7 _ B7 五、發明說明（7) 在通式[M-Zm]n-K代表之化合物中： Μ爲一具有下列結構式之順丁烯二醯亞胺部份： RV/ N— 0 式中R1爲Η或1至05烷基； Ζ爲線性或有支鏈烷基、烷基氧基、烷胺、烷硫化物 、烯烴、烯氧基、烯胺、烯硫化物、芳基、芳基氧基或芳 基硫化物等物種，可含有自該鏈懸垂或作爲該鏈部份主幹 之飽和或不飽和環狀或雜環狀取代基，且其中存在之任何 雜原子可能或可能不直接附接於Κ ； 或者Ζ爲具有下列結構之胺基甲酸乙酯： 0 〇〇 〇 一一X一C一NH^R^-N Η-Ό一(〇—(^一0—C~ N H—R3- N H-C-)~ X—一 式中R2獨立爲一具有1至18個碳原子之烷基、芳基、或芳 基烷基；R3爲一在鏈內有高至100個原子之烷基或烷基氧 基鏈，該鏈可含有芳基取代基；X爲0、S、N或P ;而乂 爲〇至50 ; 或者Z爲具有下列結構式之矽氧烷·· -(CRS )e-[SiR42-〇]f-SiR42-(CR12 )g-式中每一位置之R1取代基獨立爲Η或一具有1至5個碳原 子之院基團，且每一位置之R4取代基獨立爲Η 、一具有1 至5個碳原子之烷基團、或一芳基團，而e及g獨立爲1 至10且f爲1至50 ; κ爲一由具有下列結構式（v)至（X II)之芳香族基團 本紙張尺度適用中國國家標準（CNS)A4規格（210 x 297公 (請先閱讀背面之注意事項再填寫本頁) 裝---- 訂-丨 經濟部智慧財產局員工消費合作社印製 137570966 經濟部智慧財產局員工消費合作社印製 五、發明說明（8) 中選出之芳香族基團（雖然僅有一鍵可予顯示以代表與芳 香族基團K之連接，但此將被視爲代表任何如以n所述及 定義之額外鍵數）： (V) (V!)
式中p爲1至100 ; (VII)
(請先閱讀背面之注意事項再填寫本頁) -I * i n iM— n i ii ϋ 一-ejΓ ϋ n n n n n i I » 式中R5、R6及R7爲線性或有支鏈烷基、烷基·氧基、烷胺、 烷硫化物、烯烴、烯氧基、烯胺、烯硫化物、芳基、芳基 氧基、或芳基硫化物等物種，可含有自該鏈懸垂或作爲該 鏈部份主幹之飽和或不飽和環狀或雜環狀取代基，且其中 存在之任何雜原子可能或可能不直接附接於該芳香族環； 或者R5、R6及R7爲具有下列結構式之矽氧烷： -(CR^ )e.[SiR42-〇]f-SiRS-(CH3 )g- 式中R1取代基爲Η或一具有1至5個碳原子之烷基團，且 每一位置之R4取代基獨立爲一具有1至5個碳原子之烷基 團或一芳基團，而e爲1至10且f爲i至5〇; 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公&) ---- 570966
經濟部智慧財產局員工消費合作社印製 Λ7 Β7 五、發明說明（9)
(XII)
而m爲0或1 ，且11爲1至6 〇 較佳之順丁烯二醯亞胺化合物尤其用作可再加工性組 合物者爲N-丁基苯基順丁烯二醯亞胺及恥乙基苯基順丁烯 二醯亞胺0 乙烯基化合物 適用於本發明黏著劑組合物之乙烯基化合物（非本文 中之順丁烯二醯亞胺類）具有下列結構式：
對於此等特定結構，當小寫"η ”爲整數1時，該化合 物將爲一單官能化合物；而當小寫"η "爲整數2至6時， 該化合物將爲一多官能化合物。 在此等結構中，Κ1及Κ2爲Η或一有1至5個碳原子之 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297坌 (請先閱讀背面之注意事項再填寫本頁)
570966 Λ7 B7 五、發明說明（10) 烷基；或與形成乙烯基團之碳形成一 5至9個成員之環狀 (請先閱讀背面之注意事項再填寫本頁) 物；B 爲 C、S、N、0、C(0)、O-C(O)、◦(0)-〇、C(0)NH、 或C(0)N(R8 )，其中R8爲Cl至C5烷基；m爲〇或1 ; η爲 1-6 ;而X、Q、Z及Κ均如上述。 B 較佳爲 0、C(0)、C(0)-0、C(0)NHSC(0)N(R8)； B 更佳爲 0、C(0)、0-C(0)、C(0)-0、或 C(0)N(RM ◦ 作爲黏著劑之較佳乙烯基化合物爲乙烯基醚或稀硫化 物〇合宜乙烯基化合物之實例如下： 〇 0 ⑶私叫\s / a(ch 如 ch3 及 \/。-(CH2)36-。. 其他組合物成份 經濟部智慧財產局員工消費合作社印製 視該封裝包覆劑所將黏結之基質之本質而定，包覆劑 亦可含有偶聯劑。本文中所用偶聯劑爲一含有供與順丁烯 二醯亞胺及其他乙烯基化合物反應之可聚合官能基團以及 一能與存在於基質表面上之金屬氫氧化物縮合之官能基團 之化學物種。此等偶聯劑及在特定基質組合物內之較佳用 量均已知於業界。合宜之偶聯劑爲矽烷、矽酸酯、金屬丙 烯酸酯或甲丙烯基酸酯、鈦酸酯、及含有鉗合配位體譬如 膦、硫醇、及乙醯乙酸鹽之化合物0當存在時，偶聯劑典 型用量高至順丁烯二醯亞胺及其他單官能乙烯基化合物之 1〇重量％，而較佳量爲〇·ΐ-3·〇重量％ 〇 此外，各包覆劑組合物含有對所得已固化組合物賦予 額外撓性及韌性之化合物。此等化合物可爲任何Tg爲或小 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297兮&)_ 570966 A7 B7 五、發明說明（n) 於5 0 °C之熱硬性或熱塑性物質，且典型爲以圍繞化學鏈自 由旋轉、存在醚基團、及欠缺環狀物結構爲特徵之聚合物 質〇合宜之此等變性劑包括聚丙烯酸酯、聚（丁二烯）、 聚THF (聚合四氫呋喃）、CTBN (羧基端接丁腈）橡膠、 及聚丙二醇Q當存在時，韌化用化合物典型用量約高至順 丁烯二醯亞胺及其他單官能乙烯基化合物之15重量％ 〇 若砂氧綜部份不爲順丁烯二醯亞胺或乙烯基化合物結 構之一部份，則矽氧烷可添加於各封裝包覆劑配方以賦予 彈性〇合宜之矽氧烷爲甲丙烯氧基丙基端接之聚二甲基矽 氧烷及胺基丙基端接之聚二甲基矽氧烷，可購自聯合化學 技藝公司及其他公司〇 亦可添加種類及用量均爲業界熟練人士已知之其他添 加物，譬如黏著促進劑〇 操作特性 此等組合物將在晶片黏附用黏著劑之商業可接受範圍 內操作〇對80 X 80平方密耳矽晶片之黏著劑商業可接受晶 片剪力値在室溫時之範圍爲大於或等於1千克，而於240 °0時爲大於或等於〇·5千克，而對50ϋχ500平方密耳晶片 之彎曲量在室溫時爲小於或等於70微米〇 熱膨脹係數（CTE)爲旣定物質每單位溫度變化之尺寸 之變化。不同物質將具有不同之膨脹率。若附接於一處之 各元素爲不同之CTE ，則熱循環會導致各附接之元素彎屈 、破裂、或層離〇在典型半導體總成中，晶片之CTE範圍 爲2或3ppm/t：;對於有機電路板基質，CTE大於30 ppm 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297 (請先閱讀背面之注意事項再填寫本頁) 裝·-------—訂'------- 經濟部智慧財產局員工消費合作社印製 570966 Λ7 Β7 五、發明說明（12) / t ;因此，黏著劑之CTE最佳爲介於基質與晶片者〇 當聚合物受到加熱時，將經由一介於堅硬玻璃狀態至 柔軟橡膠狀態之轉換區域移動◦此區域稱爲玻璃轉變區域 或Tg 〇若繪製聚合物之膨脹對溫度之圖形，玻璃轉變區域 爲較低溫度/玻璃狀區域熱膨脹係數與較高溫度/橡膠狀 區域熱膨脹係數間之交點〇高於此區域，膨脹率顯著增高 〇因此，該聚合物之玻璃轉變溫度較佳爲高於塗施期間所 經驗之正常操作溫度，而在需要可再加工性時，玻璃轉變 溫度較佳爲低於任何再加工溫度〇 本發明之另一具體形式包括各種具有本文中所述通式 [M-Xro]n-Q及[M-Zm]n-K之順丁烯二醯亞胺，式中Q及Z 可爲具有下列結構式之酯： 0 0 0 〇
1 II II II II 一卜-。一 ¢- r3- ci—〇—r3 ” δ—' R广 δ ~ 〇一 或下列結構之酯： :? 0 0 0 卜3_ C— R3冬。-。一尺3— 0- C一 R^4p~ 1 式中p爲1至100 ; 每一:R3可獨立爲一在鏈內有高至1 00個原子之烷基或烷基 氧基鏈，該鏈可含有芳基取代基；或者 具有下列結構式之矽氧烷： -(CR12)e-[SiR42-〇]f-SiRS-(CR12)g-式中每一位置之R1取代基獨立爲Η或一具有1至5個碳原 子之烷基團，每一位置之W取代基獨立爲一具有1至5個 本紙張尺度適用中國國家標準（CNS)A4規格（21〇 X 297 (請先閒讀背面之注意事項再填寫本頁) Γ
經濟部智慧財產局員工消費合作社印製 570966 Λ7 ___ 137______ 五、發明說明（13) 碳原子之烷基團或一芳基團，e及g獨立爲1至10，且f 爲1至50 〇 本發明之另一具體形式包括具有下列本文中所述結構 式之乙烯基化合物：
式中 B 爲 C、 S、 N、 0、 C(0)、 0-C(0)、 C(0)-0、 C(0)NH、 或C(0)N(R8)，其中^爲^至^烷基ο 本發明之另一具體形式包括具有下列本文中所述結構 式之乙烯基化合物： (請先閱讀背面之注意事項再填寫本頁)
經濟部智慧財產局員工消費合作社印製 式中Q及Ζ可爲具有下列結構式之酯： 〇 〇 0 0 〜R，。- C - R3-C -。- R3 1R3-各-。- R34jj 或下列結構之酯： 〇 0 0 0 一|(V C— 0— R3-〇一。一 R34 C— 0—R3-〇-C-R34p·
I 式中p爲1至100 ; 每一R3可獨立爲一在鏈內有高至1〇〇個原子之烷基或烷基 氧基鏈，該鏈可含有芳基取代基；或者 具有下列結構式之矽氧烷： 本紙張尺度適用中國國家標準（CNSM4規格（210 X 297~i^ 570966
五、發明說明（14) -(CR1 2 )e-[SiR4 2 -0]f-SiRS -(CR12 )g- (請先閱讀背面之注意事項再填寫本頁) 式中每一位置之P取代基獨立爲H或一具有1至5個碳原 子之烷基團，每一位置之R4取代基獨立爲一具有1至5個 碳原子之烷基團或一芳基團，e及g獨立爲1至1〇,且£ 爲1至50 〇 本發明之另一具體形式包括如本文中所述含有陰離子 性或陽離子性固化起發劑之可固化黏著劑組合物0此等起 發劑之類型及有用量均詳知於業界〇 實例 將各種順丁烯二醯亞胺及乙烯基化合物製備及配製成 黏著劑組合物。該等組合物予調查未固化組成之黏滯度及 觸變指數，以及已固化組成之固化態樣、玻璃轉變溫度、 熱膨脹係數、熱機械分胡1、及一些情況下之可再加工性。 實例1 丁二烯一歴稀腈雙順丁烯二醯亞胺之製備 H2^rγ^^NHί ch3 ‘丄八/ 經濟部智慧財產局員工消費合作社印製
C三N
CH,
1·罐了瑪=酸断内_ I 2. Ac20, NaOAc, Et3N
本紙張尺度適用中國國家標準（CNS)A4規格（210 x 297坌 570966 經濟部智慧財產局員工消費合作社印製 Λ7 B7 五、發明說明（15) 胺基端接之丁二烯一丙烯腈（BF Goodrich公司所售 Hycar樹脂1 3 0 0 XU ATBN ，該結構內之m及11整數提供 3600之數平均分子量）（4 5 0克，50 0毫摩爾，以胺當量 AEW =450克爲準）溶解於配備以添加用漏斗、機械攪拌器 、內部溫度探針及氮氣入口 /出口之3升裝四頸燒瓶內之 CHC13 (1000毫升）中0將已攪拌之溶液置於氮氣下並於 冰浴上冷卻。將在C H C 13 ( 5 0毫升）中之順丁烯二酸酐（ 9 8 · 1克，1摩爾）注入添加用漏斗內，並以3 〇分鐘時間將 此溶液加於反應內，而內部反應溫度維持低於1 〇 ec 〇此混 合物於冰上攪拌3 0分鐘，然後溫熱至室溫並額外攪拌4小 時0對所得獎液添加乙酸酐（Ac20) (65ΰ·4克，6摩爾） 、三乙胺（Et3N) (64·8克，0.64摩爾）及乙酸鈉（NaOAc) (62 · 3克，0 · 7 6摩爾）〇將反應加熱至溫和迴流溫度達5 小時，讓其冷卻至室溫，並續用水（1升）、飽和碳酸氫 鈉（1升）及水（2X1升）萃取〇於眞空移除溶劑以產生 順丁烯二醯亞胺端接之丁二烯丙烯腈〇 實例2 製·^由三（環氧基丙基）異m尿酸衍φ夕 丁烯二醢亞胺）
本紙張尺度適用中國國家標準（CNS)A4規格（210 x 297含 (請先閱讀背面之注意事項再填寫本頁)
570966 A7 B7 五、發明說明（16)
解於配備以機械攪拌器、內部溫度探針及氮氣入口 /出口 之2升裝三頸燒瓶內之THF ( 500毫升）中。對此溶液添 加羥基苯基順丁烯二醯亞胺（189 ·2克，1摩爾）及苯甲 基二甲基胺（1 .4克，0·ϋ5重量％ ) 〇該溶液加熱至80 達7小時〇然後讓反應冷卻至室溫，過濾，並用5 %氯化 氫水液（5 0 0毫升）及蒸餾水（1升）沖洗濾液。所得三 氮哄三（順丁烯二_亞胺）固體於室溫予眞空乾燥〇 實例3 順丁烯二醯亞胺某棕櫚酸酯之製備 --------------裝--- (請先閱讀背面之注意事項再填寫本頁) -1丨訂： 經濟部智慧財產局員工消費合作社印製
0 1 H3C(H2C)14/SCI 0 H〇"\/N，
ο ο
棕櫚醯氯（274 ·9克，1摩爾）溶解於配備以機械攪 拌器、內部溫度探針、添加用漏斗及氮氣入口 /出口之2 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297 570966 A7 _ B7 五、發明說明（17) 升裝三頸燒瓶內之二乙醚（5 0 〇毫升）中。添加在蒸餾水 (5 0 0毫升）中之碳酸氫鈉（8 4 · 0克，1摩爾），劇烈攪 拌，並於氮氣下之冰浴上將溶液冷卻〇將在二乙_( 1 〇 〇 毫升）中之羥基乙基順丁烯二醯亞胺（Ml克，1摩爾） 注入添加用漏斗內，並以3 Q分鐘時間將此溶液添加於反應 內，內部溫度於添加期間維持< 1 0 °C 〇在冰上另外攪拌該 反應30分鐘，然後讓其溫熱至室溫並攪拌4小時。將反應 移至分離漏斗，並用蒸餾水（500毫升）、5 %氯化氫水 液（50G毫升）及蒸餾水（2χ 5〇〇毫升）沖洗已分離之有 機層。有機物予分離，於無水硫酸鎂上乾燥，過濾並於眞 空移除溶劑，以產生脂肪族順丁烯二醯亞胺〇 實例4 製備一由5 -異氣酸鹽基(異氰酸鹽基甲某）_ 1 順丁嫌二觸亞胺 (請先閱讀背面之注意事項再填寫本頁) * ---- n n —Γ ·1 一口 r ^ n I— mmmam 1» ϋ ·
570966 A7
五、發明說明（18) 5-異m酸鹽基(異氰酸鹽基甲基卜i，3,3 -三甲基環 己烷（111 · 1 5克，0 · 5摩爾）於配備以機械攪拌器、添加 用漏斗及氮氣入口 /出口之1升裝三頸燒瓶內之THF (500 毫升）中媒合〇將反應置於氮氣下，並添加二丁錫二月桂 酸酯（觸媒S η 1 1 ) ( 6 · 3 1克，1 〇毫摩爾）及羥基乙基順丁 烯二醯亞胺（1 4 1克，1摩爾）同時攪袢，且於7 (TC將所 得混合物加熱4小時。將溶於THF (1〇ϋ毫升）中之徑基 乙基順丁烯二醯亞胺（141克，1摩爾）注入添加用漏斗 內0以30分鐘時間將此溶液添加於異氰酸鹽溶液，所得混 合物於7 0 °C額外加熱4小時。讓反應冷卻至室溫並於眞空 移除溶劑〇將殘留之油溶於CH2 C 12 ( 1升）中，並用1 0 % 氯化氫水液（1升）及蒸餾水（2 X 1升）沖洗〇已分離之 有機物於硫酸鎂上乾燥，過濾並於眞空移除溶劑，以產生 順丁烯二醯亞胺〇 實例5 製備由P r i ρ ο 1 2 0 3 3衍生之二聚乙烯B沫
雙（1,10-啡啉）Pd(0Ac)2 ( 0·21 克，0·54毫摩爾）在 氮氣下溶解於配備以機械攪拌器之2升裝三頸燒瓶內之丁 基乙烯基醚（8.18克，81.7毫摩爾）、庚烷（1〇〇毫升） 與'"二聚二醇"（由Unichema公司以Pnpol 2 0 3 3銷售， 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公# --------------裝--- (請先閱讀背面之注意事項再填寫本頁) 訂.· 經濟部智慧財產局員工消費合作社印製 570966 A7 B7 五、發明說明（19) 15.4克，27. 2毫摩爾）所成混合物中。該溶液加熱至輕緩 迴流達6小時〇讓溶液冷卻至室溫，並續倒於活性碳（2 0 克）上且攪拌1小時〇過濾所得漿液，並於眞空移除超量 之丁基乙烯基醚及庚烷以產生爲黃色油之乙烯醚0生成物 顯現可接受之4 NMR、FT-IR及13C NMU光譜特性。黏滯 度典型爲〜1 〇 〇厘泊。 實例6 製備由二聚二醇（Pripol 2033)衍生 t二聚二丙烯酯 ,
二聚二醇（Unichema公司之Pripol 2033 ， 284.4 克 ，500毫升）在氮氣下溶解於配備以機械攪拌器、添加用 漏斗、及內部溫度探針之1升裝三頸燒瓶內之無水丙酮（ 500毫升）中。對此溶液添加三乙胺（1〇1 ·2克，1摩爾 )，並在冰浴上將溶液冷卻至4 °C 〇將媒合於無水丙酮（ 100毫升）中之丙烯醯氯（90.5克，1摩爾）注入添加用 漏斗內，並以60分鐘時間添加於已攪拌之反應溶液，內部 溫度維持< 1 〇 °C 〇在冰上額外攪拌此溶液2小時，然後讓 其溫熱至室溫並攪拌4小時〇經由旋轉蒸發器移除全部溶 劑，並於CH2 Cl2 ( 1升）中將殘留物媒合〇該溶液用5 % 氯化氫水液（8 0 0毫升）及水（2 X 8 0 0毫升）沖洗〇已分 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297兮 (請先閱讀背面之注意事項再填寫本頁) -I · ϋ n n n I L· .1^-r^Jit n t ί ϋ n ϋ n I · 經濟部智慧財產局員工消費合作社印製 570966 Λ7 B7 五、發明說明（20) 離之有機物於無水硫酸鎂上 ，以產生二丙烯酯油0 實例7 N-乙某苯某順丁烯二醯亞胺 將4-乙基苯胺（12.12 並緩慢添加於9 · 8 1克順丁烯 冷卻無水乙醚中之攪拌溶液 攪拌30分鐘。將淡黃色結晶 毫升）溶解順丁烯醯胺酸及 160 °C油浴中加熱。迴流3 置於1升裝燒杯內之冰水中 物並於己院中再結晶0收集 乾燥過夜〇 FTIR及NMR分析 特性◦ 實例8 雙（烯硫化物）之製備HCr\ 乾燥，過濾並於眞空移除溶劑 之製備 克）溶於 二酸酐在 〇添加完 過濾及乾 2〇克之乙 小時後， 並劇烈攪 之晶體物 顯示出乙 50毫升之無 10U毫升於 畢後，反應 燥。用乙酸 酸鈉0反應 將溶液冷卻 拌1小時〇 質於5 0°C眞 基順丁烯二 水乙醚中 冰浴中所 混合物予 酐（2 0 0 混合物於 至室溫， 吸濾生成 空烘箱內 _亞胺之 (請先閱讀背面之注意事項再填寫本頁)
D 0JI X 〇 cw 0H 經濟部智慧財產局員工消費合作社印製 觸媒η 52 ο οΑΑ0. ^,(CH2)1〇CH3 3C(H2C)i0^S^ 本紙張尺度適用中國國家標準（CNS)A4規格（2〗0 x 297 570966 Λ7 B7 五、發明說明（21) (請先閱讀背面之注意事項再填寫本頁) 二聚酸（以Unichema公司Empol商標銷售）（ 5 7 4·6 克，1摩爾）及炔丙醇（1 12 · 1克，2摩爾）於配備以機 械攪拌及Dean-Stark蒸餾裝置之3升裝三頸燒瓶內之甲苯 (1升）中媒合◦添加濃硫酸（’ 5毫升）並迴流該溶液6 小時，直到共沸蒸餾出36毫升之水爲止。讓溶液冷卻至室 溫，用水（2 X 1升）沖洗，於無水硫酸鎂上乾燥，並於眞 空移除溶劑以產生爲油之炔丙酯中間產物〇
此酯中間產物（6 5 0 . 7克，1摩爾）在氮氣下於配備 以迴流冷凝器、機械攪拌器、及內部溫度探針之1升裝三 頸燒瓶內之THF ( 2ϋϋ毫升）中媒合。添加月桂基硫醇（ 404.8克，2摩爾）及2, 2’-偶氮雙（2,4-二甲基戊睛） (以DuPont公司Vazo 52商標銷售，11克），並於油浴上 將所得混合物攪拌加熱至7 Q°C達7小時◦讓反應冷卻至室 溫並於眞空移除溶劑，以產生烯硫化物油〇 實例A 6-順丁烯二醯亞胺基己酸之製備 6-順丁烯二醯亞胺基己酸
0 經濟部智慧財產局員工消費合作社印製 用已知之方法合成酸功能性順丁烯二醯亞胺，即6 -順 丁烯二醯亞胺基己酸〇胺基己酸（100克，7.6X10-1摩 爾）溶解於配備以機械攪拌、內部溫度探針及添加用漏斗 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公g) 570966 A7 B7 五、發明說明（22) (請先閱讀背面之注意事項再填寫本頁) 之500毫升裝四頸燒瓶內之冰醋酸（50毫升）中。將順丁 烯二酸酐（74.8克，7·6χ1〇-ι摩爾）溶解於乙腈（75毫 升）中之溶液注入添加用漏斗內〇於室溫以1小時時間將 此溶液添加於胺基己酸，內部反應溫度維持小於3 5 °C 〇添 加完畢後將反應攪拌3小時〇將反應發液過濾，於7 0°C眞 空烘箱（P〜25 T)內將分離之濾液乾燥過夜，以產生166 及灰白色固體（95%) 〇生成物醯胺酸顯現與文獻資料一 致之FT-IR及1H NMR光譜特性〇 經濟部智慧財產局員工消費合作社印製 上述醯胺酸（I66克，VJXlO-1摩爾）於氮氣下在 配備以機械攪拌及Dean-Stark蒸餾裝置之1升裝三頸燒瓶 內之甲苯（2〇〇毫升）、苯（2〇〇毫升）與三乙胺（211 毫升，1 · 5 1摩爾）之溶液中媒合。將此溶液加熱至迴流溫 度達4小時，並將所生成之水收集於Dean-Stark阱內〇添 加蒸餾水（4 0 0毫升）於反應燒瓶以溶解生成物之三乙銨 鹽，後者在反應期間自總溶液大量分離Q將此水液層分離 ，用50%氯化氫予酸化至pH〜1 ，並用乙酸乙酯（600毫 升）萃取〇此有機層用蒸餾水（4 0 0毫升）沖洗〇已分離 之有機層於硫酸鎂上乾燥，繼於眞空移除溶劑以產生灰白 色固體（76· 2克，50% ) 〇生成物6-順丁烯二醯亞胺基己 酸在FT-IR及1H NMR攝譜術上與文獻物質相同〇 實例Β a二聚二酯雙順丁烯二醯亞胺〃之製備 a二聚二酯雙順丁烯二醯亞胺〃（及環狀異構物） 缮)- 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297 570966 A7
五、發明說明（23)
Γ%先閱讀背面之、注意事項再填寫本頁}
Pripol 2033 (11111(：1^1]^公司、、二聚二醇"，92.4克 經濟部智慧財產局員工消費合作社印製
，1·69χΐ0_ι摩爾）、6-順丁烯二醯亞胺基己酸（75·〇克 ，3 · 5 5 X 1 0 - 1摩爾）及硫酸（〇 · 5 0毫升，〜8 · 5 X 1 0 - 3摩 爾）於氮氣下在配備以機械攪拌器、Dean-Stark阱及內部 溫度探針之1升裝四頸燒瓶內之甲苯（：300毫升）中製漿 0將反應加熱至輕緩迴流逹二小時，並將所生之水收集於 Dean-S tai*k阱內〇該阱予洩流並將〜50毫升之甲苯溶劑餾 離反應，以移除微量水分並將酯化平衡驅至完成。讓反應 冷卻至室溫，添加額外之甲苯（1 0 0毫升）（實驗室規模 上，於此處較佳爲添加二乙醚替代甲苯），並用飽和碳酸 氫鈉水液（ 3 0 0毫升）及蒸餾水（ 300毫升）沖洗溶液。 將有機層分離及於無水硫酸鎂上乾燥，並於眞空移除溶劑 以產生橘色油（107.2克，68%) 〇通過一*短柱之砂石或 礬土流洗樹脂之甲苯溶液可將該物質進一步純化〇此雙順 丁烯二醯亞胺樹脂液體顯現可接受之FT-U 、1 NMR、及 1 3 C NMR資料〇 r丨典型爲〜2 5 00厘泊〇 實例C _vv癸嫁二醇二酯雙暖J烯二醯亞胺〃之製遍 a癸烷二醇二酯雙順丁烯二醯亞胺" ^紙張尺度適用中國國家標準（CNS)A4規格（21〇 X 297公1) "— 一
570966 Α7 _ Β7 五、發明說明（24) 0 ; t 人。 6 〇
應用實例B中所述之一般步驟，用癸烷二醇（2 9 · 5克 ，1.69Xl〇-1摩爾）取代Pripol 2033 〇此程序產生中度 可溶性之雙順丁烯二醯亞胺固體（54 · 9克，58 % )〇生成 物顯現令人滿意2FT-IR及1H NMR資料〇 實例D ♦甘油三酯三（順：Γ烯二醯亞胺）〃之製備 0 0=^ 0 (請先閱讀背面之注意事項再填寫本頁) 〇 經濟部智慧財產局員工消費合作社印製 〇 人》^N ,、 il 0 利用實例B所列約定，用甘油（1 o . 4克，1 · 1 3 x 1 0- 1 摩爾）取代p r i ρ ο 1 2 ϋ 3 3 0生成物爲黏稠液體，顯現可接 受之FT-IR及1 Η ΝΜΚ資料。 實例Ε 製備a IPDI之雙（m-硝基苯甲基胺基甲酸i旨）〃
N 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297兮&)_ 〇Λ. Ο 異 摩爾） 及二丁 氣下於 2升裝 溶液加 異氰酸 )沖洗 體，後 實例F Μ vv 570966 A7 B7 五、發明說明（25) A IPDI之雙（m-硝基苯甲基胺基甲酸酯）〃 佛爾酮二異氰酸酯（"IPDI "，10U · 0克，4 · 5 X ΙΟ-ν m-硝基苯 甲基醇 （137.8 克， 9.0X10-1 摩爾） 基錫二月桂酸酯（2·8克，4·5Χ10-3摩爾）在氮 配備以機械攪拌器、迴流冷凝器及內部溫度探針之 三頸燒瓶內之無水甲苯（1500毫升）中媒合。所得 熱至90°C達4小時。試樣固體部份之IR中未觀察到 酯波帶。讓溶液冷卻至室溫並用蒸餾水（10 〇毫升 〇將有機層分離並於眞空移除溶劑，以產生黃色液 者顯現可接受之FT-IR及1 Η NMK特性〇 IPDI之雙（m-胺基苯甲基胺基甲酸酯）〃 (請先閱讀背面之注意事項再填寫本頁) NH2
經濟部智慧財產局員工消費合作社印製 ♦ IPDI之雙（m-胺基苯甲基胺基甲酸酯）〃 實例£之二硝基化合物（8.28克，1.57\10-2摩爾） 在氮氣下溶解於配備以磁攪拌之5 0 0毫升裝三頸圓底燒瓶 內之乙醇（1〇〇毫升）中。添加環己烯（28 · 6毫升，2 · 82 X 10-1摩爾），繼以5 % Pd/C (鈀/碳）（4.14克）〇所 得漿液輕緩迴流6 · 5小時。此溶液一過濾等分量之FT- I R 於1 529厘米及1 3 5 2厘米·：不顯現硝基伸展波帶〇讓總溶 液冷卻至室溫並過濾〇於眞空移除溶劑以產生黃色半固體 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公 570966 A7 B7 五、發明說明（26) {請先閱讀背面之注意事項再填寫本頁}
(6.6克，90% )，後者顯現可接受之FT-IR及1Η NMK光 譜特性〇 實例G 製備a IPDI之雙（dM噴丁烯二醯亞胺菽采甲基
a IPDI之雙（m-順丁烯二醯亞胺基苯甲基胺基甲酸酯）〃 實例F之二胺（6·6克，1·41χ1〇ι摩爾）在氮氣下 於配備以機械攪拌器及添加用漏斗之2 5 0毫升裝四頸燒瓶 內之丙酿（60毫升）中媒合，並冷卻至4 eC 〇以30分鐘時 間將溶解於丙_ (20毫升）中之順丁烯二酸酐（2. 76克， 經濟部智慧財產局員工消費合作社印製 2 . 82 X 10- 2摩爾）〇所得溶液於4 °C攪拌1小時，並績讓 其溫熱至室溫並攪拌過夜〇 FT- I β分析指示無剩餘之順丁 烯二酸酐，如由〜1 8 1 0厘米-1處缺少酐伸展波帶所判定〇 對上醯胺酸溶液添加乙酸酐（8·5毫升，9 ,ϋ X 10- 2 摩爾）、三乙胺（I·26毫升，9·〇Χΐ〇·3摩爾）及乙酸鈉 (0·88克，1.1Χ10-2摩爾）〇所得溶液於氮氣下輕緩迴 流4小時。讓反應冷卻至室溫並於眞空移除全部溶劑〇所 得黏稠液體於二氯甲烷（2 〇 〇毫升）中再媒合，並用蒸餾 水（ 3 X 200毫升）萃取〇於是有機物及於無水硫酸鎂上乾 燥，過濾並於眞空移除溶劑以產生淺褐色固體（6.75克， 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公爸)_ 570966
經濟部智慧財產局員工消費合作社印製 A7 ____B7_____ 五、發明說明（27) 76 % ) 〇此物質顯現可接受之FT-IR及1 Η NMK光譜特徵。 實例Η 製備、、D D I 1 4 1 0之雙（m _硝某苯甲基胺基甲酸酯）〃
▲ DD1 1410之雙（m-硝基苯甲基胺基甲酸酯）〃 (及環狀異構物）
DDI 1410 (Henkel 公司 a 二聚二異氰酸酯"，99,77 克，1 · 65 X 10 - 1摩爾，以13 · 96 % NC0爲準）、m-硝基苯 甲基醇（50·8克，3.32Xl〇d摩爾）及二丁基錫二月桂酯 (0.3毫升，8·3 X 1G-4摩爾）在氮氣下於配備以機械攪 拌器、迴流冷凝器及內部溫度探針之1升裝四頸燒瓶內之 甲苯（1 5 0毫升）中媒合。將反應加熱至8 5 °C達2 . 5小時 〇該反應一等分量之FT-IU分析指示異氰酸酯官能基團完 全消耗，如由2 2 7 2厘米-1處缺少波帶所判定〇於眞空將溶 劑移離該反應，以產生黃色油，後者靜置於溫度時固化（ 152 ·4克，1〇2 % (微量甲苯））〇此固體顯現令人滿意 之FT-IR及1H NMR光譜特徵〇 實例I 製備a DDI 141〇之雙（m-胺某_苯甲基胺某甲酸酯）" 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公 (請先閱讀背面之注意事項再填寫本頁)
570966 A7 B7 五、發明說明（28) 0 Η 、0八、丨 m〇
--------------裝--- (請先閱讀背面之注意事項再填寫本頁) a DDI H10之雙（m-胺基苯甲基胺基甲酸酯）〃 (及環狀異構物）
實例Η之二胺生成物（39.6克，4.32X10-2摩爾）及 二水合氯化亞錫在氮氣下於配備以機械攪拌器及迴流冷凝 器之1升裝三頸燒瓶內之乙酸乙酯（3 ϋ ϋ毫升）中製漿。 將反應加熱至輕緩迴流並劇烈攪拌3小時〇讓溶液冷卻至 室溫並用飽和碳酸氫鈉之溶液帶至pH 7-8 〇將混合物推過 2 5微米過濾器，以產生一分離成混濁水液層及中度清澈有 機層之混合物。將水液層分離並用乙酸乙酯（1 0 0毫升） 沖洗0將有機層結合，用蒸餾水（3 0 0毫升）萃取，並於 無水硫酸鎂上乾燥。過濾漿液並於眞空將溶劑移離濾液， 以產生黃色黏性固體（Μ . 8克，92 % ) 〇 實例J 經濟部智慧財產局員工消費合作社印製 製備^ DDI 1410之雙（m-順丁烯二醢亞胺基苯甲基 胺某甲酸酯）
本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公 經濟部智慧財產局員工消費合作社印製 570966 A7 B7 五、發明說明（Μ) ^ D D 1 1 4 1 ϋ之雙（m -順丁烯二醯亞胺基苯甲基 胺基甲酸酯）〃（及環狀異構物） 順丁烯二酸酐（1 5 · 4克，1 · 5 7 X 1 0 - 2摩爾）溶解於配 備以機械攪拌器、內部溫度探針及添加用漏斗之2升裝四 頸燒瓶內之丙酮（3 00毫升）中。此溶液在冰洛上冷卻至 〜4 °C 〇將實例I所製備二胺（63· 4克，7·48 X 10-2摩爾 )在丙_ (70毫升）中之溶液注入添加用漏斗內，並以30 分鐘時間添加於順丁烯二酸酐溶液，而內部溫度維持< 10 °C 〇將所得溶液攪拌1小時，並續讓其溫熱至室溫並攪拌 2小時〇 對此醯胺酸溶液添加乙酸酐（24 · 7毫升，2 . 61 X 10 - 1 摩爾）、三乙胺（6·25毫升，4.48X10-2摩爾）及四水合 乙酸鎂（0.37克，1.50Χ 10-3摩爾）〇此溶液予輕緩迴流 6 · 5小時，然後讓其冷卻至室溫〇於眞空移除全部溶劑， 並將所得暗色液體溶解於二乙醚（ 500毫升）中〇此溶液 用蒸餾水（5 0 0毫升）沖洗〇然後用飽和碳酸氫鈉水液（ 5〇〇毫升）並再用蒸餾水（ 5 00毫升）沖洗已分離之有機 層〇有機物予分離，於無水硫酸鎂上乾燥，並於眞空移除 溶劑以產生黏稠之橘色油◦此物質顯現與預期之雙順丁烯 二醯亞胺生成物一致之FT-IR、1 Η ΝΜΚ及"c NMR光譜特 徵。 實例ΑΑ 低應力晶..片__Μ.附用黏著劑配方及在各種引線框 上之晶片抗剪强麻 本紙張尺度適用中國國家標準（CNS)A4規格⑵G X 297公g) (請先閱讀背面之注意事項再填寫本頁)
570966 A7 B7 五、發明說明（30) (請先閱讀背面之注意事項再填寫本頁) 於室溫用機械混合器將以下結合生成黏滯度爲19 011厘 泊（5 rpm ，圓錐及平板）及觸變指數爲5.36之填銀晶片 黏附用黏著劑配方： 實例B之液體雙順丁烯二醯亞胺 2 · 644克 實例5之二聚乙烯醚 2 · 644克
Ricon 131MA20 (Kicon 樹脂公司） ϋ.6ΰ1 克
Silquest A-174 (Witco 公司） 0·ϋ40 克 USP-90MD(Witco 公司） 0.099 XD002 6 ( NSCC公司简業機密） 0.119 SF-96 銀片 23.794 所得糊劑如下詳述予分配於不同金屬引線框上，並將 1 2 0 X 1 2 0密耳矽晶片置於黏著劑珠上以生成約i密耳之黏 結線。各試樣於200 °C a急速固化〃 60分鐘，並於室溫及 24 0 °C測量晶片抗剪强度。然後，此等試樣受到高溫及濕 度（85 °C / 85% RH)達48小時〇然後於室溫及240 °C再次 測量晶片抗剪强度◦各項結果表列於表I 〇 表1 :順丁烯二醯亞胺/乙烯醚晶片黏附用 經濟部智慧財產局員工消費合作社印製 黏著劑之晶片抗剪强度（DSSj__ 不暴露於水 暴露於水後 (48小時 /85 eC /85 RH) 固化態樣 _6 0 秒 / 2 ϋ 0。。_ _ 6 0 / 2 0 0 °C_ 测試溫度 2 5〇C 2 4 0 °C ‘2 5°C 2 4 0 °C 銅引線框 4,88+/- 1 .46 + /- 6.54+/- 1.84+/- DSS(千克） 0.25 0.35 ϋ ,82 0.76 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公g) 570966 銀銅引線框 5.29+/- 2 · 17 + /- 9,50+/- 1 · 56 + /- DSS(千克） 0.34 0 .43 1.88 0 .72 鈀銅 5.52 + /- 1.99+/- 11.9+/- 3.53+/- DSS(千克） 0 .39 0 .44 1，3 0.66 A7 ____B7 五、發明說明（31) 此等元件在8 5 °C / 8 5 % Μ飽和後之典型水分攝取量爲0 . 1 8 重量％ 〇固化期間重量損失爲〇 . 16 + /-ϋ . 05重量％ 〇 實例ΒΒ 順丁烯二醯亞胺/乙烯_晶片黏附用黏荖劑之hast測試 利用實例AA之黏著劑組合物，以類似實例AA之方式將 1 20 X 1 20密耳晶片黏附於各種不同組成之引線框〇然後用 v'急速固化〃（60秒/ 2 0 0 °C)及a快速烘箱固化〃（15 分鐘/ 1 7 5 eC )之條件將已黏結晶片固化〇所得已固化元 件接受模擬之HAST测試條件（130 °C，《5 % M)達13〇小 時〇如表2所示，各元件於室溫及高溫顯現良好之以晶片 抗剪强度（DSS)所量度之黏著力〇 表2 在模擬HAST測試條件後之晶片杭前 (請先閱讀背面之注意事項再填寫本頁) 經濟部智慧財產局員工消費合作社印製 固化態樣 6 ϋ 秒 / 2 0 (TC 1 5 分鐘 / 1 7 s 測試溫度 2 5°〇 24 0 °C 2 5〇C 銅引線框 15.3+/- 1.12+/- 17.2+/- 丄· 2 5 + DSS(千克） 1 . 8 0.35 (K 8 0.39 銀銅引線框 16.3+/- 2.81+/- 14.8+/- 2.6 + DSS(千克） 1 .9 0.55 1.8 1 . 6 鈀銅 15.7+/- 3.04+/- 14.4+/- 2.96 + DSS(千克） 1 .7 0.46 U . 7 0.90 本紙張尺度適用中國國家標準（CNS)A4規格mo X 297 570966 A7 _____ B7_ 五、發明說明（3 2)
實例CC (請先閱讀背面之注意事項再填寫本頁) 用順丁烯二醯亞胺/乙烯醒晶片黏附用 -_黏著劑所黏結大晶片之彎曲 使用實例A A中所述晶片黏附用組合物將5 0 0 X 5 0 〇密耳 晶片黏結於鈀一銅引線框0於若干溫度及時間將已組裝之 物件vv急速固化"，並測量晶片彎曲量°典型結果列示於 表3 〇此黏著劑所顯現之性能使其符合v低應力〃物質〇 表3 :順丁稀二醯亞胺/乙稀魅晶片黏附用 _黏荖劑在50 0 X 50 0密耳晶片上之蠻曲 熱史 1分鐘/ 2 0 0 °C +1分鐘/24〇1 +4小時/175°〇 彎曲（微米）1〇, 4+/-1.3 11.9 + /-1.4 14 . 1 W-1 . 6
實例DD 順丁烯二酿亞胺/乙烯醚晶片黏附用黏著劑之熱分析 使用實例AA之組合物以一向下拉引棒生成〜1密耳之 膜。各膜在熱板上、、急速固化〃（60秒，2 00 °C)或予烘 箱固化（4小時/ 1 7 5 °C )，並藉動態機械分析（A )予 以定性。各項結果摘列於表4 〇 經濟部智慧財產局員工消費合作社印製 表.4_AJlr烯二醯亞胺/乙烯_晶片黏附膜之熱分析 固化態樣—___(30秒/ 200 〇C 4小時/ 1 7 5。。
Tg ( eC ) -1 35 〜65°C 模數（E，）（psi) 4 2 1,3 0 0 5 1 3,9 0 0 1 〇 〇 °C 模數（E，）（ p s i ) 5,8 64 2 3,9 8 0 各物質顯現之模數低於低應力黏著劑之典型Tg 〇高於 Tg之溫度時各物質之模數足以承受典型之線黏結條件，而 本紙張尺度適用中國國家標準（CNs)A4規格（210 X 297坌&)_ 570966 A7 B7 五、發明說明（33)
不故障〇 實例EE (請先閱讀背面之注意事項再填寫本頁) 矽氧烷雙順丁烯二醯亞胺之製備 甲醇末端矽氧烷（DMS-C15 ，Gelest公司；2 7.2 6克 ，27.2毫摩爾）及Ν,Ν-二甲基胺基枇啶（DMAP; 0.07克， 經濟部智慧財產局員工消費合作社印製 〇 · 55毫摩爾）在氮氣下於配備以機械攪拌器、添加用漏斗 及內部溫度探針之500毫升裝四頸燒瓶內之CH2C：U (2〇〇 毫升）中媒合0此溶液在冰浴上冷卻至〜5 °C 〇將二環己 基碳二醯胺（DCC ; 14.6克，68.1毫摩爾）在CH2C12 (50 毫升）中之溶液注入添加用漏斗內。此UCC溶液於45分鐘 時間內添加於該矽氧烷/ UMAP溶液，同時將內部溫度維持 < 1 0 °C 〇此溶液於冰浴上攪拌2小時，此時，該溶液一等 分量之FT-IR分析指示有酯（174〇厘米及殘餘DCC ( 2120厘米〃）存在〇讓該溶液溫熱至室溫並額外攪拌三小 時。將乙酸（20毫升）添加於該反應並額外攪拌一小時， 此時，FT- I Κ指示無殘餘DCC 〇將該溶液過濾移除沉澱之 二環己基尿素（DC ϋ )，並於眞空將溶劑移離濾液。剩餘之 油於己烷（2 ϋ 0毫升）中再媒合，並冷卻至〜5 達一週 。所得溶液自沉澱之帶紅色固體過濾以產生一淺褐色溶液 〇此溶液於室溫與矽膠（1 ϋ克）製漿達-小時，過濾並於 眞空移除溶劑，以產生一淺褐色溶液，後者顯現可接受之 1 H NMR、2 9 Si NMR及 FT-IK 光譜特徵 〇
0 〇 本紙張尺度適用中國國家標準（CNS)A4規格（210x 297兮夢)_ 本 口 申請曰期 90 04.10 案 號 90108606 類 別 \公/处 (以上各欄由本局填註） A4 C4 570966 !專利説明書 中 文 發明 新型 名稱 英 文 姓名 國 籍 用於微電子元件之可固化黏著劑組合物
A CURABLE ADHESIVE COMPOSITION FOR USE IN MICROELECTRONIC DEVICES 唐諾赫爾 裝 發明 創作 人 住、居所 稱 名 美國 美國賓州多樂城柏拉路125號 司 公 股 控 資 投 學 化 及 粉 澱 民 國 商 美 嘬 訂 線 Γ .VI tJL >»ν>1 乂广？ ！'>— 1 Π.;·/ i .Ti印梵 申請人 國 籍 住 、居所 (事務所） 代 表人 姓 名 美國 美國德拉瓦州威明頓銀翼路3411號諧和廣場 本紙張尺度適用中國國家標準（CNS ) Λ4况格（2 10X 297公犛）

Claims (1)

  1. 570966
    (92·03·31·修正）
    1· 一種可固化黏著劑組合物，用於將電子組件黏合於 基質，包含一順丁烯二醯亞胺化合物及一爲0.1至10重量 %之由自由基起發劑、光起發劑、及其等之組合形式所組 成集團中選出之固化起發劑，該順丁烯二醯亞胺化合物具 有通式[M-Xm]n-Q ，式中η爲1至6 ，m爲1或2 ，而 (a ) Μ爲一具有下列結構式之順丁烯二醯亞胺部份：
    式中R1爲Η或具有1至5個碳原子之烷基； (b) X爲一由具有下列結構式之芳香族基團中選出之芳香 族基團：
    l (iv)
    (c ) Q爲具有下列結構式之酯： 〇 〇 Ο II II —R8·—C一〇—R3—Q-C— R8— 式中R3爲具有下列結構式之矽氧烷： -(CR1i)Q - (〇)1>0 -(CR^HSi-R^-Or-Si-^CR^WO),^ ~(CR12)g ~
    570966 申請專利範圍續頁 式中每一位置之R1取代基獨立爲Η或一具有1至5個碳原 子之烷基團，R8爲一具有1至20個碳原子之直線或有支鏈 烷基或烯氧基，每一位置之R4取代基獨立爲一具有1至5 個碳原子之烷基團或一芳基團，e及g獨立爲1至10，而 f爲1至50 〇 2·—種可固化黏著劑組合物，用於將電子組件黏合於 基質，包含一順丁烯二醯亞胺化合物及一爲0.1至10重量 %之由自由基起發劑、光起發劑、及其等之組合形式所組 成集團中選出之固化起發劑，該順丁烯二醯亞胺化合物具 有通式Mn-Q，式中η爲1至6 ，而 (a ) Μ爲一具有下列結構式之順丁烯二醯亞胺部份： ,\ N—— / 〇 式中R1爲Η或具有1至5個碳原子之烷基； (b ) Q爲具有下列結構式之酯： 〇 〇 —R8一c一〇—R3—0-C— R8— 式中R3爲具有下列結構式之矽氧烷： -(cr12)q ~ (〇)1ι0 ^CR12)e^Si-R%^)r^HR42-~(CR12)g-{〇)1；0 ~(CR12)〇 - 式中每一位置之R1取代基獨立爲H或一具有l至5個碳原 子之烷基團，R8爲一具有1至20個碳原子之直線或有支鏈 570966 申請專利範圍續頁 烷基或烯氧基，每一位置之R4取代基獨立爲一具有1至5 個碳原子之烷基團或一芳基團，e及g獨立爲1至10，而 f爲1至50 〇 3 .如申請專利範圍第2項之可固化黏著劑組合物，其 中該順丁烯二醯亞胺化合物具有下列通式：
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CN1252144C (zh) 2006-04-19
KR20010100882A (ko) 2001-11-14
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HK1041712A1 (en) 2002-07-19
CN1321715A (zh) 2001-11-14

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