TW200427724A - Composition and method to achieve reduced thermal expansion in polyarylene networks - Google Patents
Composition and method to achieve reduced thermal expansion in polyarylene networks Download PDFInfo
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- TW200427724A TW200427724A TW92133362A TW92133362A TW200427724A TW 200427724 A TW200427724 A TW 200427724A TW 92133362 A TW92133362 A TW 92133362A TW 92133362 A TW92133362 A TW 92133362A TW 200427724 A TW200427724 A TW 200427724A
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- polyarylene
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- 238000000034 method Methods 0.000 title description 14
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- 150000001875 compounds Chemical class 0.000 claims description 38
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Description
玖、發明說明: t發日月戶斤屬之技術領域】 敘述 美國政府在本發明中具有已付款的許可證且在有限的 U况下具有權利用以要求專利權所有人在合理的條件下授 權他人,如經國家標準暨技術院(NIST)合作協定條款第一—_ 號中所規定者(高科技方案)。 發明領域 本發明淪及在鬲溫下顯示降低之熱膨脹的聚伸芳基低 聚合物以及聚合物。本發明亦論及使用在高溫下具降低之 熱膨脹的聚伸芳基介電質體所製成的積電路物件。
【月1J ilL 發明背景 -、、、、、只❿彡又運性此及岔度的努力已經迫使古 級材料以及互連結構的使用。互連性能需要電阻與電容: p牛低。銅金屬化係於1998年被採用以降低互連佈線 阻二在本發明說明書中用來似介電質指代之電容降低或^ “電常數絕緣體的引入為未來的性能增進所需要。一 過去25年以來,二氧化發已經作為半 絕緣體的選擇。二氧切持有優異的介質,二二電 Κ強化學瘵乱沈積法(PECVD)的障壁罩層 材料的優胸著。^,隨綱規 降= 對於改進性能的需要,二氧化倾緩慢地被二::: 二寺有較低’丨電係數的材料所取代以達到降低〜 正取在許多的應用中在⑽_的技術節點下氣例 正取代二氧化矽。 矾矽酸鹽破璃 在130醜的技術產生下,“真㈣,,低 +導體產品中。有數 包貝係破履行 列主要者·妙^㈣料但是工業上已經專注於下 介電質。;有機聚合物以及摻碳的peCVd二氧化石夕 之間=rf可被作為在微電子元件中介於數個電路 〜叫的乡巴緣層以及名命 積體電路j Η 層的使用,鱗電路諸如 以狀模組以及積層電路板。微電子製造工業 :月:件之較小的幾何形狀發展以能夠減低功率且加快 =。呈如導體線變為更細且更緊密地堆積,介於此等導 "間之介電質料求變為更嚴格。 。5物"笔處通常提供比無機介電質(諸如二氧 )幸乂低的;1黾$數,聚合物介電質通常呈現對製造期間 、秘序正口的困難。例如,作為一種在積體電路中用以取 代二氧化矽的介電質,聚合物介電質必須要能夠耐得任在 金屬化期間的加J1溫度以及該程序的徐冷步驟。較值地, ;1包材料應該具有一大於加工溫度的玻璃轉移溫度。又, 忒"電材料必須保有在元件使用條件下所欲的特質。例 如,该介電材料不應該吸收水份,因水份可造成金屬導體 的介電常數與潛在腐蝕的增加。 WO 98/11149揭示介電聚合物,該等介電聚合物為/環 戊_烯酮官能基化合物與一乙炔官能基化合物的反應虞物 且係被使用於微電子的製造。 聚合物介電質(諸如在W〇 98/11149中所揭示的聚伸芳 基材料)的一個缺點為隨著溫度增加,其熱膨脹係數(在此用 CTE來指代)顯著性增加。在聚合物介電質的CTE隨著溫度 之顯著性增加造成在該介電CTE與該等金屬互連線中的大 規模的失配。互連製造方法需要多次從2〇〇c到4〇〇°C(且有 些情況下到450QC)的溫度偏移。在一多層互連結構的製造 中,對該結構或物件被暴露於4〇〇cC-45〇cC歷經5-1〇個小時
為平常的。介於聚合物介電質與金屬線(銅或鋁)之間的cTE 失配壓迫障壁金屬隔離器層,可能地造成隔離器不連續性 (即在隔離器層的破裂)。在可靠性試驗期間,於熱循環試驗 期間顯示出CTE失配,經由結構不合標準可靠性資格而^ 該處被單離。 鑒於目前技藝水平,需要一經改質的聚合物介電 降低於整個加工範圍期間介於聚合介電質之CTE與〜二1 (諸如銅或鋁)之間的失配。 、金屬 【發明内容】 發明概要 介電質,該綱介 ,數與該聚合物介電質之間最小的失配以避免於:)= ^間金屬結構的損害。因此,根據_第_個具體實二"衣 叫發明論及-積體電路物件,該物件包含—包括至 喊的活性基質以及-形成—電互連結構之金屬線的圖= =中該等金屬線為^部分地以_ 在本發明的積體電路物件中,該聚伸芳㈣=所分 _侧溫度範固期間持有一小於 之低k介電質’較佳地小於刚ppm/QC。在本發明中所使用 的術語“低k”係代表—具有小於3G之介電t數的介電材 料,較佳地小於2.6。 在第-個具體實施例中所描述之本發明的積體電路物 件可包括-聚伸芳基材料,該材料為狄爾斯-阿德耳⑼ Alder)與介於至少_種具有二個或多個二稀官能基團的化 10合物與至少-種具有二個或多個親二稀體官能基團的化合 物之間的苯乙炔熟化反應的產物,其中至少該等化合物之 一者具有三個或多個該等官能基團。 在第一個具體實施例中所描述之積體電路物件可包括 木伸芳基材料,该材料為至少一具有二個或多個環戊二 15烯酮S能基團的化合物與至少一具有二個或多個乙炔官能 基團的化合物之反應產物,其中至少該等化合物之一者具 有三個或多個該等官能基團。 杈佳地,在第一個具體實施例中所描述之積體電路物 件包括一聚伸芳基材料,該材料為3,3,-(氧化二-i,4-伸笨基) 20雙(2,4,5-三苯基環戊二烯酮)與1,3,5-三(苯基乙炔基)笨的反 應產物。 更佳地’在第一個具體實施例中所描述之積體電路物 件包括一聚伸芳基材料,該材料為3,3’-(氧化二伸苯基) 雙(2,4,5-三苯基環戊二烯酮)與^^三(苯基乙炔基)笨的反 9 200427724 應產物,其中該二種單體之化學計量莫耳比係分別地介於 0.7/1 與 0.99/1 之間。 本發明的第二個具體實施例為一經熟化的聚伸芳基材 料,該材料為狄爾斯-阿德耳與介於至少一種具有二個或多 5 個二烯官能基團的化合物與至少一種具有二個或多個親二 烯體官能基團的化合物之間的苯乙炔熟化反應的產物,其中 至少該等化合物之一者具有三個或多個該等官能基團;該聚 伸芳基材料具有一於350°C-425°C的溫度範圍内為小於110 ppm/°C之熱膨脹係數,該係數係由熱機械分析所決定。 10 較佳地,在第二個具體實施例中所描述之聚伸芳基材 料為一其中該等二烯官能基團為環戊二烯酮基團且該等親 二烯體官能基團為乙炔基團者。 在第二個具體實施例中所描述之聚伸芳基材料可包括 至少一種具有親二烯體官能基團的化合物,該化合物包含 15 一具有二個親二烯體基團的第一化合物與一具有多於二個 親二稀體(dieneophile)基團的第二化合物。 在第二個具體實施例中所描述之聚伸芳基材料可為一 種其中該第二化合物具有三個親二烯體基團的材料。 本發明的第三個具體實施例為一經熟化的聚伸芳基材 20 料,該材料包含3,3’-(氧化二-1,4-伸苯基)雙(2,4,5-三苯基環 戊二烯酮)與1,3,5-三(苯基乙炔基)苯的反應產物,其中該等 單體的化學計量莫耳比係分別地介於0.7/1與0.99/1之間,其 中該聚伸芳基聚合物已經在至少一 405°C的溫度下歷經至 少一個小時被熟化被熟化,其中該聚伸芳基持有一於 10 200427724 350°C-425°C的溫度範圍内為小於110 ppm/°C的熱膨脹係 數,該係數係由熱機械分析所測定。 在第三個具體實施例中,聚伸芳基材料為一種其中佳 的單體比為0.9/1之材料。 5 更準確地說,在第三個具體實施例中所描述的聚伸芳 基材料為一種其中較佳的熟化成型為410°C共90分鐘或 415QC共60分鐘之材料。 本發明的第四個具體實施例論及一種積體電路物件, 該物件包含一種含有電晶體的活性基質、一種包含一種金 10 屬線圖案的電互接結構以及一種至少部份地分開該等金屬 線之於第三個具體實施例中所述之聚伸芳基材料。 圖式簡單說明 第1圖為熱膨脹係數(CTE)與用於一系列聚伸芳基材料 介電樣本之溫度關係曲線圖,為一化學組成物(即莫耳化學 15 計量法)與熟化條件的函數。 I:實施方式】 詳細說明 本發明申請人具有一出乎意料的發現,即一積體電路 物件,該物件需要一種聚合物介電質,該聚合物介電質具 20 有一介於金屬熱膨脹係數與該聚合物介電質之間最小的失 配以避免於熱循環期間金屬的損害。因此,根據第一個具 體實施例,本發明論及一積體電路物件,該物件包含一包 括至少電晶體的活性基質以及一形成一電互連結構之金屬 線的圖案,其中該等金屬線為至少部分地藉由一有機聚合 11 200427724 材料所分離,較佳地為一種聚伸芳基材料。應該注意到, 術語“聚伸芳基”以及“聚伸苯基”係同義地遍及本發明中同 義地所使用。在本發明的積體電路物件,聚伸芳基材料介 電質遍及從200°C到425°C的溫度範圍持有一小於110 5 ppm/°C的 CTE,較佳地小於 100 ppm/°C。 在此所使用之術語“聚伸芳基”係代表一種主要地包含 直接地鍵結至其他芳環之芳環的材料。這些芳環可為苯 環;經取代的苯環;稠芳族系統(諸如萘、蔥、菲、苐)以及 經取代的稠芳環。在聚伸芳基聚合物鏈中可具有連接基 10 團,諸如氧、硫、颯、亞颯、胺、磷、矽、脂族碳基團、 羰基、羧基等等,以分隔一些芳環。在芳環上的取代基團 實質上可為惰性或可為可進一步反應且/或鍵結二個或多 個聚伸芳基聚合物鏈一起的活性反應組分。 較佳的聚伸芳基為一種具有二個或多個二烯官能基反 15 應基團的化合物以及一種具有二個或多個親二烯體官能基 反應基團的化合物之反應產物。該等較佳的聚伸芳基為交 連材料;因此,至少某些該等化合物必須具有三個或多個 反應基團。該等較佳的聚伸芳基(包括先質b-部分聚合階段 可熟化的低聚合物)典型地具有下列化學式:
20 [A]W[B]Z[EG]V 其中A具有下列結構: 12 200427724
其中EG為具有一個或多個下列結構的末端基團:
[机三 Jy-iAri~ R2-^~ ——Ar?— 其中R1以及R2係個別地為H或一個未經取代的或經惰性地 取代的芳族部分;Ar1、Ar2以及Ar3係個別地為一個未經取 代的芳族部分或經惰性地取代的芳族部分;Μ為一鍵;Y為 10 一個三或更大的整數;Ρ為在特定的基體單元中未經反應的 乙炔基團的數目;r為在特定的基體單元中經反應的乙炔基 團的數目減去一;p+r=y-l ; z為一個從1到1000的整數;w 13 200427724 為一個從0到1000的整數;且V為一個為2或更大的整數。 此等低聚合物及聚合物可藉由一雙環戊二稀酮與一含 有三個或多個乙炔部分之芳族乙炔的反應而被製備。 此一反應可由下列化學式的化合物之反應所代表: 5 (a)—雙環戊二稀酮的化學式如下:
(b)—多官能性乙炔的化學式如下: [RiHr-Ar3 其中R1、R2、Ar1、Ar3以及y為先前所界定者。 10 芳族部分的界定包括苯基、多芳族以及稠芳族部分。 經惰性地取代意指取代基團實質上對環戊二烯酮以及乙炔 聚合反應為惰性的且不易於在微電子元件中具環境種類 (諸如水)之經熟化聚合物的使用之條件下反應。此等取代基 團包含,例如,F、(^、Br、-CF3、-OCH3、-OCF3、-O-Ph、 15 一含有從1到8個碳原子的烷基以及一含有從3到8個碳原子 的烷基環烷基。例如,該等可為未經取代之或惰性地經取 代之芳族部分的部分包括如下: 14 200427724
其中Z可為如下:-〇-、-S-、伸烷基、-CF3-、-CH2-、 -〇-CF2-、全氟烴基、全氟烷氧基,
其中各個R3獨立地為-H、-CH3、-CH2CH3、-(CH2)2CH3或Ph ’ 例如苯基。 15 200427724 另一個較佳聚伸芳基低聚合物及聚合物的基團可由下 列化學式所代表:
其中P代表增長中的分枝低聚合物/聚合物鏈且具有下列重 5 覆結構:
Γ 且其G基圑為填滿價的末端基團,在該處低聚合物/聚合物 成長尚未發生且具有下列結構:
10 其中R1及R2係獨立地為Η或未經取代之或惰性地經取代之 芳族部分;Ar4為一芳族部分或一惰性地經取代之芳族部 分;i和j為大於或等於1的整數,但須i+j為大於或等於3 ;且 η和m為大於或等於0的整數,但須n+m為大於或等於1。此 一聚合物可藉由下列多官能化合物通式之環戊二稀酮官能 15 度與乙炔官能度的反應所製備: 200427724
其中R1、R2以及Ar4為先前所界定者。
一種含有二個或多個芳族環戊二烯酮部分的多官能化 合物可使用習知的方法藉由二苯乙二酮與苄基酮的縮合反 5 應所製成。例示的方法係被揭示於,例如,Kumar等人的巨 分子(Macromolecules),1995,28,124-130 ; Ogliaruso等人 的有機化學期刊(J. Org. Chem·),1965,30, 3354; Ogliamso 等人的有機化學期刊(J· Org. Chem.),1963,28,2725 ;以 及美國專利第4,400,540號中。上文揭露的各個内容係在此 10 被併入以為參考。
一種有二個或多個芳族乙炔部分的多官能聚合物可藉 由習知的方法所製成。一種芳族化合物可被鹵化且然後在 一種芳基乙炔化作用觸媒的存在下與適當之經取代的乙炔 反應以用經取代的乙炔化合物置換鹵素。聚合反應步驟可 15 藉由已被揭示的方法的使用而被進行,例如,在WO 98/11149中者,該内容係在此被併入以為參考。 聚伸芳基根據任何已知的方法可被施加至積體電路元 件’諸如’例如溶液沈積法、液相蠢晶法、網版印刷、溶 融紡絲、浸塗、輥筒護膜、紡絲、刷光(例如以一清漆)、喷 20 塗膜、粉末塗層、電漿鍍、分散喷霧、溶液鑄造、漿體喷 17 200427724 霧、乾燥粉末喷霧、流體化床技術、熔接、包括引線爆炸 喷霧以及爆炸接合的爆炸方法、在熱的情況下之壓接合、 電漿聚合[反應]、在一分散介質中且其次排除該分散介質的 分散[作用]、壓力接合、在壓力的情況下之熱接合、氣體環 5 境加硫、擠製熔融聚合物、熱氣體熔接、烘焙、塗覆以及 燒結。單-以及多層膜亦可使用藍牟耳技術 (Langmuir-Blodgett technology)在空氣-水或其他界面被沈 積於一基質上。較佳地,可熟化的聚伸芳基低聚合物係藉 一有機溶劑被旋轉塗覆於該基質上。 10 合適的有機溶劑包括但不被限定於如下:莱、吡啶、 三乙胺、N-曱基吡咯烷酮(NMP)、苯甲酸甲酯、苯甲酸乙 酯、苯曱酸丁酯、環戊酮、環己酮、環庚酮、環辛酮、環 己基吡咯烷酮以及其他或羥基醚,諸如二节醚、二甘醇二 曱醚、三甘醇二曱醚、二甘醇二乙醚、二甘醇曱醚、雙丙 15 二甘醇甲醚、雙丙二甘醇二甲醚、甲苯、二甲苯、苯、雙 丙二甘醇一甲醚乙酸、二氯苯、丙稀碳酸酯、萘、二苯 醚、丁内酯、二曱基乙醯胺、二曱基曱醯胺以及其等之混 合物。 可被使用於本發明中之較佳的溶劑為莱、N-曱基吡咯 20 烷酮(ΝΜΡ)、γ-丁内酯、二苯醚、環己酮以及其等之混合物。 在塗覆之後,低聚合物或聚合物較佳地係被暴露於足 以提升該低聚合物或聚合物至一較高分子量的溫度且在最 佳的實施例中,至一具所欲熱膨脹係數的交連聚合物。 本發明的積體電路物件可根據任何已的方法而被製 18 200427724 成,諸如那些以矽或砷化鎵所製造者。典型地,一積體電 路具有藉由一種或多種絕緣材料所分離的多層金屬導體。 聚伸芳基可被使用為介於在同一層的個別金屬導體間以及 /或介於互連結構之導體層間的絕緣。聚伸芳基亦可與其他 5材料的組合以一組成的互連結構的形式而被使用,諸如其 他旋塗式有機物、無機物或有機-無機混成物,其他具 SiCON、氟化旋塗式玻璃(FSG)、以〇2或以3队之組成物的 CVD材料。例如,可被製成的積體電路元件被揭示於美國 專利第5,55〇,405號;美國專利第5,591,677號;Hayeshi等人 10的1996年於超大型積體電路科技的科技論文摘要的討論會 (1996 Symposium on VLSI Technology Digest of Technical Papers),88-89頁;以及w〇 98/11149。 本發明的積體電路可藉由任何已知的方法而被製成, 诸如一 “金屬鑲嵌法,,金屬嵌體或除去雜物的金屬圖案化 15圖。用於製造金屬鑲嵌法線以及介層的方法為習知的。參 照’美國專利第5,262,354號以及美國專利第5,093,279號。 材料的圖案化可以典型的反應性離子蝕刻(RIE)方法 被完成,該等方法係使用氧、氬、氮、氦、二氧化碳、含 氣化合物或其等之混合物以及其他氣體且使用一種光阻 2〇 軟罩諸如,例如,一種環氧酚醛清漆)或一種結合一無機 硬罩”的光阻(諸如,例如,Si〇2、Si3N4或一種金屬)。 聚伸芳基可和由下列方法所沈積的鋁(A1)、鋁合金、 鋼、銅合金、金(Au)、銀(Ag)、鎢(w)以及其他的一般金屬 導體材料(用於傳導性線以及插頭)結合而被使用:物理蒸氣 19 200427724 沈積法、化學蒸氣沈積法、蒸發、電鍍、無電沈積法以及 其他沈積方法。至基本的金屬4體之額外金屬層(諸如钽、 欽、鐫、鉻、姑、其等之合金或其等之L)可被使用以 填坑、加強金屬填充、力口強附著、提供一障壁或改良金屬 5 的反射性。 視製造的設訂而疋 10 15 20 發明的介電材料可使用 學機械拋光技術而被移除或被平坦化 本發明申請人具有-出乎意料的發現,對於積體電路 物件,為了使物件於建_間得以耐得住減環以及接下 來的熱循環可靠性試驗而在金屬介層中*生成缺陷或缺 失,如藉由張力下的厚膜於舰條件下之熱機械分析所測 量到,遍及從2(K)°C到425°c的溫度範圍小於u〇 ppmTC, 較佳地小於UK)卯心’的聚伸芳基介電質之最大熱膨脹 係數為所需的。 發現到-特定聚伸芳基喊物與熟化條件(即轨處理) 的獨一性組合得到對聚伸芳基材料介電質之-顯著地降低 之熱膨脹係數。為了達到聚伸芳基組成物,—種二官能性 稀化t物(較佳地為雙環戊二稀酮)以及-種三或高官能 I·生親-稀MUm三6炔)係被反應。料單體的莫耳比 係被改善而導致在生成的經熟化樹脂之交連密度上的變 成的經熟化樹脂之交連密度且降低在高溫時的 丄、、化條件,諸如熟化的溫度及時間,在交連密 度上具有放應且因此影響在高溫時的㈣㈣熱膨㈣ 化 20 200427724 數。例如,若熟化的溫度不足以允許交連反應來完成,線 路的交連密度為低的且因此在高溫時的熱膨脹係數為高 的。結果,熱膨脹係數可藉由控制熟化溫度及時間而被減 至最小值。即,較高的熟化溫度以及較長的熟化時間可在 5在。00。0的溫度導致一較低的熱膨脹係數。為了在高溫達 到最低的CTE,熟化溫度較佳地不低k4〇5〇c,更佳地為歷 經從約60到約100分鐘的_段時間從約4〇5〇c到約化义且 甚至更佳地為歷經從約40到約70分鐘的一段時間於從約 410°C到約420°C的溫度。舉例來說,歷經45分鐘於4〇〇〇c 10經熟化之低CTE配方的某些樣本於4〇〇〇c具有12〇±5的 CTE,而歷經90分鐘於41〇〇c經熟化之相同配方的樣本於 400°C具有93±5的CTE。 所陳述的下列實施例係用以敘述本發明且不應被構成 限制本發明的範疇。在該等實施例中,除非另作說明,部 15 分以及百分比均以重量計。 isi施例1 乙炔化合物三(笨乙基)茉 一乙月女(375 g)、三苯膦(4·7865 g)、乙酸鈀(1〇2〇5 g) 、及Ν,Ν —甲基曱醯胺(2〇〇〇 ml)係被裝入裝配有一熱電 禺 頂邛機械攪拌器、一冷凝器、一附加漏斗以及一具 旧酿度控制器的加熱罩之一 5公升的3·頸圓底燒瓶中。這個 混合物係被攪拌歷經5分鐘以溶解觸媒。然後,二乙胲(5 g) I’3,、二/臭笨(190 g)以及笨乙炔(67.67 g)係被添加。反 21 200427724 應器係用氮吹洗歷經15分鐘,且然後被加熱至7〇〇c同時維 持一氮大氣壓。在於70〇C加熱歷經3〇分鐘之後,笨乙炔 (133.33 g)係被緩慢一滴一滴地添加歷經丨個小時的時間,且 溫度上升至80〇c。持續的加熱再9個小時。然後反應係被冷 5部至空溫且水(1公升)係被添加以沈澱粗製產物。產物被過 濾、500 ml分的水被清洗三次、然後一次用環己烷清洗。 晶體係在75°C隔夜被真空乾燥以產生226.40 g(百分之991 的產率)經氣相層析法為97.25面積百分比純度。該等晶體係 被溶解於甲苯中(18〇〇 ml)、通過矽膠而被再過濾且溶劑被 馨 1〇移除於一旋轉蒸發器上以產生214.2 g(百分之94.2的產率) 經氣相層析法為99.19面積百分比純度。然後殘留物係從曱 苯(375 ml)舆2-丙醇(696 ml)的混合物而被再結晶。白色的 晶體係被過濾、以曱苯(100 ml)與孓丙醇(4〇〇 ml)的混合物 所清洗且在75°C隔夜被真空乾燥以產生1,3,5-三(笨乙基)笨 15 (190·0 §,百分之83.91的產率)經氣相層析法為99.83面積百 分比純度。來自曱苯/異丙醇之額外的再結晶產生可接受的 有機以及離子純度的材料。 3U氧化伸茉基)雙(2A5-三茉某璟尨二烯酮化合物Ο (a) 4,4’-二茉乙醯二茉醚 2〇 一 二苯醚(50.0 g,0.294 mol)以及苯乙醯氯(1〇2 g, 0.661 mol)的溶液係被滴加至於〇°c之二氣甲烷(200 ml)中 的一氯化鋁(97.9 g,0.734 mol)的漿體歷經30分鐘的時間。 當該添加係被完全時,使反應混合物可以升溫至周圍溫度 且隔夜擾拌。反應混合物係邊授拌邊小心地被倒入1.5 kg 22 200427724 的冰/水中。二氣甲烷(1500 ml)係被添加以溶解固體且層係 被分開。有機層係通過矽藻土而被過滤,然後被濃縮至乾 燥。自曱苯的再結晶產生110 g(百分之92)呈淡褐色棱晶的 標稱產物。 5 (b) 4,4’-雙(苯某乙二醛醯)二茉醚的製備 含水HBr(97 ml之一48重量百分比的溶液)係被添加至 一於DMSO(400 ml)的 4,4’-二苯乙醯二苯醚(97.9 g,0.734 mol)的漿體中且生成的混合物係被加熱至1 〇〇cC歷經二個 小時,然後係被冷卻至周圍溫度。該反應混合物係被分隔 10 於甲苯(5〇〇 ml)與水(750 ml)之間。有機層係用水清洗(3 χ 250 ml),接著用鹽水清洗且被濃縮以產生當處於周圍溫度 的時候凝固之一黏膠、嫩黃色的油。自乙醇再結晶產生35,9 g(百分之67)呈嫩黃色立方體的標稱產物。 (g)化合物C的舉備 15 195·4 g(0·4498 mol,1·0 eq)之雙(笨基乙二醛醯)二 苯醚、193.9 g之二苯丙酮(0.9220 mol,2.05 eq)以及2.5升去 氣乙醇係被添加至一經氮吹洗之裝配有一熱電偶、具氮入 口官的回流冷凝器以及附加漏斗的5-L模頓(Morton)燒瓶 中。5亥混合物係被加熱至回流,獲得一句相溶液且該溶液 20以氮攪動歷經30分鐘。一含有25.2 g KOH(0.4498 mol,1 〇 叫)的溶液、200 ml乙醇以及25 rnL的水係被添加至附加漏斗 中。溫度係被降低至74〇C且KOH溶液係於5分鐘内被快速地 添加。一放熱反應係被快速地建立且係被維持回流直到該 溶液的3/4被添加,此後溫度開始下降。在鹼添加的同時立 23 200427724 即觀祭到暗紫色現出且在添加完全之前觀察到固體的出 現。在添加完全之後,不句相溶液係被加熱至一強的回流 歷經15分鐘且更堅實的產物係被形成。混合物容許被冷卻 至25QC且29·7 g冰醋酸(0.4984 mol,1.1 eq)係被添加且歷經 5川刀麵被授拌。粗製產係經由過濾而被單離且用濾水、3公 升EtOH以及2公升MeOH在過濾漏斗内被清洗且在6〇〇c到 90 C真工下歷經12個小時被乾燥產生323 g(百分之92純度) 粗製DPO-CPD,該粗製DPO_CPD係藉由LC純化為百分之94 純度。經熱化的材料係被溶解於高效液相層析級(HpLC 10 grade)之二氣曱烷(10重量百分比)中、被轉移至裝配有一底 部沖洗閥以及機械攪拌器之5公升的模頓燒瓶中且歷經1〇 至90分鐘、2到7次用相同體積分的低離子水而被劇烈地清 洗。然後CHfl2溶液係被快速注入經過一5 於cH2ci2* 含有75g矽膠的官柱。該管柱係以另外丨公升CH2Cl2被清 15洗,在該處濾液為實質地澄清。溶液係被蒸發至乾燥且被 再溶劑於THF巾,再度被蒸發以除去大部分的二氯甲烧殘 留物。粉末係被轉移至一 5公升裝配有附加漏斗與腓特烈 (Friedrichs)回流冷凝器的燒瓶中且被溶解(每毫升〇 〇7至 0.Π克)於喊之錢HPLCTHFt。溶„縫吹洗歷經三 20個小時且THF係被於45°C到50°C被冷凝,同時殘留的二氯 甲烷係藉由蒸餾所移除。將一蒸餾頭靠近且7〇〇mI^,n公升 的THF被移除。然後使溶液可以經過數個小時緩慢地冷卻 至室溫,然後用冰浴被冷卻至低於丨〇〇c,期間再結晶發生。 晶體係使用-5職的PTFE過濾器於_4公升的微孔夹一玻 24 200427724 璃料吸取燒瓶中被單離。然後,晶體用1公升MeOH清洗且 於80°C到90。(:在真空下隔夜被乾燥而生成70至85百分比具 有百分之99LC純度的DPO-CPD產物,mp 270°C。 實施例2 5 自3,3’-(氧化二-1,4-伸笨基)罅K5-三茉環戊二烯酮V彳 物C)與1J,5-三(笨乙基)笨(化合物A)之一系列低聚合 液的製備以及性質量測 10 15 自3,3’-(氧化二-1,4-伸苯基)雙(2,4,5-三苯基環戊二稀 酮)(化合物C)與1,3,5-三(苯乙基)苯(化合物A)之一系列低聚 合物溶液,其中該等組分的莫耳比係不同,化合物c的莫耳 數係等於或小於化合物A者,特別是經使用以製低聚合物溶 液的莫耳數比從1 : 1(C : A)到0.8 : 1(C : A)變化。單體係 於γ-丁内酯中在百分之30固體下藉由加熱至2〇〇〇c歷經 24-48小時而被反應。溶液被冷卻至大約i3〇〇c,然後以環 己酉同被稀釋成百分之2GS]體。然後使溶液可以冷卻至空溫。 經熟化膜之熱膨脹係數係使用具有一於張力模式中的 石英機組之-熱機械分析儀所測量。7微米的膜係藉由 塗覆多層低聚合物溶液至—晶圓上所製備,接著每一層在 ,積至下_層之前t經過—卿c_5分鐘的熱板烘烤(於一 孔孔冲洗之下)。在所欲的厚度被達到之後,膜係於一供箱 20 =:生成|^之下歷經特定熟化時間及溫度而被熟化(在 曰曰□上)在4化之後’樣本係被置於水:為⑽:i的稀 釋液中以促進膜從晶圓_層。然後膜顧㈣子水清洗 且於-真空:!:共箱中在曹c歷經〜H、時而被乾燥。 25 200427724 然後膜係被切成〜2 mm χ 15 mm的條狀物且被填充於 熱機械分析儀石英張力機組。膜係在尸口分鐘從〜5〇cC被加 熱至430°C且測量膨脹。 在CTE上於400°C時介於單體比與熟化條件之間的關 5 係的實施例係被描述於第一表中。 弟1表 樣本 C : Α之莫耳 數比 熟化溫度 (°C) 熟化時間 在400°C 的 CTE (ppm/°C) A 1:1 400 ~~ 45 ---—- 139+/-6 B 1:1 415 ' —60 117+/-6 C υ.9 1 400 _45 121+/-6 D 0.9 1 400 90 106+/-6 E 0.9 1 410 1 60 101+/-6 F 0,9 1 410 ~~ 90 93+/-6 G 0.9 1 415 60 94+/-6 Η τ 0.9 1 "—--- 415 — 90 89+/-6 1 _——. 415 60 95+/-6 八㈤本發明係根據其之較佳的具體實施例而被特別地顯 且^述日守’熟悉此項技藝者了解脫離本發明精神及範疇 因迟内奋以及其他在形式上及細節上的改變可被造成。 ^ 心圖本發明並不被限制於所被描述以及被敘述之確 的心式及細㈣是落於所㈣請專職_範嘴内。 【圖式簡舉說明】 介圖為輯脹係數(CTE)與用於一系列聚伸芳基材料 ^本之•度關係曲線圖,化學組成物(即莫耳化學 叶量法)與熟化條件的函數。 【圖式之主要元件代表符號表】 (無) 26
Claims (1)
- 200427724 拾、申請專利範圍: 1. 一種積體電路物件,該物件包含一包括有至少電晶體的 活性基質,一包含一金屬線圖案的電互接結構,以及一 具有一於350°C-425°C的溫度範圍内為小於115 ppm/°C 5 之熱膨服係數的聚伸方基材料’該係數係由熱機械分析 所測定。 2. 如申請專利範圍第1項之物件,其中該聚伸芳基材料為 由至少一具有二或更多個二烯官能基團的化合物與至 少一具有二或更多個親二烯體官能基團的化合物之 10 間,進行狄爾斯-阿德耳(Diels Alder)與苯乙炔熟化反應 的一個產物,其中該等化合物中之至少一者具有三或更 多個該等官能基團。 3. 如申請專利範圍第1項之物件,其中該聚伸芳基材料為 至少一具有二或更多個環戊二烯酮官能基團的化合物 15 與至少一具有二或更多個乙炔官能基團的化合物的一 個反應產物,其中該等化合物中之至少一者具有三或更 多個該等官能基團。 4. 如申請專利範圍第1項之物件,其中該聚伸芳基材料為 3,3’-(氧基二-1,4-伸苯基)雙(2,4,5-三苯基環戊二烯酮)與 20 1,3,5-三(苯基乙炔基)苯的一個反應產物。 5. 如申請專利範圍第1項之物件,其中該聚伸芳基材料為 3,3’-(氧基二-1,4-伸苯基)雙(2,4,5-三苯基環戊二烯酮)與 1,3,5-三(苯基乙炔基)苯的一個反應產物,其中該二種單 體之化學計量莫耳比係分別地介於0.7/1與0.99/1之間。 27 6· 一種經熟化的聚伸芳基,該聚伸芳基為由至少一具有二 或更多個二稀官能基團的化合物與至少一具有二或更 夕個親一稀體官能基團的化合物之間進行狄爾斯-阿德 耳與苯乙炔熟化反應的一個產物,其中該等化合物中之 至少一者具有三或更多個該等官能基團,且該聚伸芳基 具有一於350〇C-425的溫度範圍内為小於丨丨〇 ppm/〇c 之熱膨脹係數,該係數係由熱機械分析所測定。 士申明專利範圍第6項之聚伸芳基,其中該等二燦官能 基團為%戊二烯酮基團,且該等親二烯體官能基團為乙 块基團。 8·如申請專利範圍第6項之聚伸芳基,其中至少一種具有 2二烯體官能基團的化合物包含一種具有二個親二烯 體基團的第一化合物以及一種具有多於二個親二稀體 基團的第二化合物。 9.如申請專利範圍第8項之聚料基,其巾料二稀官能 基團為環戊二烯酮基團’且該等親二烯體官能基團為乙 快基團。 瓜如申請專利範圍第8項之聚伸芳基,其中該第二化合物 具有三個親二烯體基團。 U·—種2體電路物件,該物件包含—包括至少電晶體的活 基貝 &含—金屬線圖案的電互接結構,以及至少 部份地分隔開料金屬線之如巾請專利範圍第6項之聚 伸芳基。 12· 一種經熟化的聚伸芳基,該聚伸芳基為—種—化學計量 28 200427724 莫耳比係分別地介於0.7/1與0.99/1之間之3,3’-(氧基二 -1,4-伸苯基)雙(2,4,5-三苯環戊二烯酮)與1,3,5-三(苯基 乙炔基)苯的反應產物;該聚伸芳基已經在至少一為 405QC的溫度下被熟化歷時至少一小時;該聚伸芳基具 5 有一於350°C-425°C的溫度範圍内為小於110 ppm/°C的 熱膨脹係數,該係數係由熱機械分析所測定。 13.如申請專利範圍第12項之聚伸芳基,其中最佳化學計量 莫耳比係(3,3’-(氧化二-1,4-伸苯基)雙(2,4,5-三苯環戊二 烯酮)與1,3,5-三(苯基乙炔基)苯)分別為0.9/1。 10 14.如申請專利範圍第12項之聚伸芳基,其中熟化係在一為 約405QC至約410°C的溫度下,歷時約60至約100分鐘的 時間。 15. 如申請專利範圍第12項之聚伸芳基,其中熟化係在一為 約410°C至約425°C的溫度下,歷時約40至約75分鐘時 15 間。 16. —種積體電路物件,該物件包含一包括至少電晶體的活 性基質,一包含一金屬線圖案的電互接結構,以及至少 部份地分隔開該等金屬線之如申請專利範圍第12項之 聚伸芳基。 29
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TWI568757B (zh) * | 2014-08-29 | 2017-02-01 | 羅門哈斯電子材料有限公司 | 聚伸芳基材料 |
TWI624489B (zh) * | 2015-07-06 | 2018-05-21 | 羅門哈斯電子材料有限公司 | 聚伸芳基材料 |
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ATE526359T1 (de) * | 2004-06-10 | 2011-10-15 | Dow Global Technologies Llc | Verfahren zur herstellung eines nanoporösen dielektrischen films |
CN101100420B (zh) * | 2006-07-06 | 2010-12-29 | 中国科学院化学研究所 | 合成3,3’-(氧联二-1,4-亚苯基)双(2,4,5-三苯基环戊二烯酮)的方法 |
US9752051B2 (en) * | 2015-04-06 | 2017-09-05 | Rohm And Haas Electronic Materials Llc | Polyarylene polymers |
US11042093B2 (en) * | 2017-11-15 | 2021-06-22 | Rohm And Haas Electronic Materials Llc | Gap-filling method |
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US6359091B1 (en) | 1999-11-22 | 2002-03-19 | The Dow Chemical Company | Polyarylene compositions with enhanced modulus profiles |
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TWI624489B (zh) * | 2015-07-06 | 2018-05-21 | 羅門哈斯電子材料有限公司 | 聚伸芳基材料 |
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