TWI636095B - 含有具特定末端構造之聚合物的熱硬化性樹脂組成物 - Google Patents
含有具特定末端構造之聚合物的熱硬化性樹脂組成物 Download PDFInfo
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- TWI636095B TWI636095B TW103120705A TW103120705A TWI636095B TW I636095 B TWI636095 B TW I636095B TW 103120705 A TW103120705 A TW 103120705A TW 103120705 A TW103120705 A TW 103120705A TW I636095 B TWI636095 B TW I636095B
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- 239000001816 polyoxyethylene sorbitan tristearate Substances 0.000 description 1
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- 238000002360 preparation method Methods 0.000 description 1
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- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G14/00—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00
- C08G14/02—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes
- C08G14/04—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols
- C08G14/06—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols and monomers containing hydrogen attached to nitrogen
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- C08G14/00—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00
- C08G14/02—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes
- C08G14/04—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols
- C08G14/12—Chemically modified polycondensates
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- C—CHEMISTRY; METALLURGY
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/013—Fillers, pigments or reinforcing additives
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C08L61/34—Condensation polymers of aldehydes or ketones with monomers covered by at least two of the groups C08L61/04, C08L61/18 and C08L61/20
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C09J161/00—Adhesives based on condensation polymers of aldehydes or ketones; Adhesives based on derivatives of such polymers
- C09J161/34—Condensation polymers of aldehydes or ketones with monomers covered by at least two of the groups C09J161/04, C09J161/18 and C09J161/20
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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
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- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
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- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
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- General Chemical & Material Sciences (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Epoxy Resins (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Wire Bonding (AREA)
Abstract
本發明之課題係提供一種新穎的熱硬化性樹脂組成物。
本發明之解決手段為一種熱硬化性樹脂組成物,其係含有具下述式(1-a)所示之重複構造單位及下述式(1-b)所示之末端構造之聚合物:
(式中,R1及R2各自獨立地表示氫原子、碳原子數1~4之烷基、苯基或碳原子數3~6之環狀烷基,X表示單鍵或2價的有機基,Y表示2價的有機基);
(式中,Q表示碳原子數1~5之伸烷基、氫原子之至少1個可經鹵素原子取代之伸苯基、或含有至少1個氮原子之5員環或6員環之2價的飽和雜環基,R3表示氫原子或甲基)。
Description
本發明係關於含有新穎的聚合物之熱硬化性樹脂組成物;及由該熱硬化性樹脂組成物所得之成形體及硬化物;以及在製造IC晶片等所代表之半導體裝置的步驟中,將被積層物間進行接著之接著劑組成物、或用於倒裝晶片接合之底部填料組成物。
近年來,伴隨著行動電話、IC卡等電子機器之高機能化及小型化,正謀求半導體裝置之高積體化。作為其手法,正檢討半導體元件本身之微細化、將半導體元件間進行縱向堆積之堆疊構造。在堆疊構造之製作中,於半導體元件間之接合時係使用接著劑。
在堆疊構造之製作中,作為於基板上安裝IC晶片之方法,係已知倒裝晶片接合。其係於IC晶片複數設置凸塊(突起狀端子),並使該凸塊與基板的電極端子進行電氣連接之方法。接著,為了填埋該基板與IC晶片
之間隙,以自濕氣及外部應力保護IC晶片,係使用底部填料劑。作為底部填料劑,係採用含有環氧樹脂之組成物(例如專利文獻1及專利文獻2),過去主要使用在將基板與IC晶片進行凸塊連接後注入底部填料劑(後入型底部填充),並使其熱硬化之方法。然而,隨著凸塊之小型化、窄間距化及IC晶片之大型化進展,底部填料劑之後入變得困難。因此,一般認為在切割晶圓前,於附凸塊的晶圓上預先形成底部填料劑,然後使經切割之IC晶片進行倒裝晶片接合之先入型底部填充係成為今後主流。
此外,作為用於使半導體元件進行接著之接著劑,係已知含有環氧樹脂之接著劑組成物(例如專利文獻3)。
此外,作為另外的堆疊構造之作成方法,係已知WOW(wafer-on-wafer,晶圓對晶圓)構造的半導體裝置之製造方法(例如專利文獻4)。
且說,已知含有於主鏈具芳香族苯并環的化合物之熱硬化性的樹脂組成物(例如專利文獻5及專利文獻6)。並且,亦已知苯并樹脂具有優異的耐熱性、電氣特性。
〔專利文獻1〕日本專利第4887850號公報
〔專利文獻2〕日本專利第4931079號公報
〔專利文獻3〕日本專利特開2008-201998號公報
〔專利文獻4〕國際公開WO2010/032729號
〔專利文獻5〕國際公開WO2007/129640號
〔專利文獻6〕國際公開WO2009/008468號
然而,在上述之倒裝晶片接合中,由於在底部填料劑之接合後,便迅速地連接凸塊,因而就如專利文獻3中所記載之過去的接著劑而言,由於接著劑以未硬化之狀態瞬間暴露於高溫,故而避免孔隙的產生係有所困難。
此外,就專利文獻4中所記載之WOW(晶圓對晶圓)構造而言,有在完全不產生孔隙之情形下將晶圓與晶圓進行接著之必要,故而成為孔隙的成因之低分子成分或耐熱性低而會進行分解之成分的應用係有所困難。
另一方面,就專利文獻5及專利文獻6中記載之含有於主鏈具芳香族苯并環的化合物之熱硬化性的樹脂組成物而言,交聯密度低且在玻璃轉移點以上的溫度之線膨脹係數高,而會有由熱歷程所造成之破裂或剝落等可靠性低下之疑慮。
再者,作為公知的技術,已知於苯并樹脂中混合環氧樹脂,以使交聯密度提升。然而,上述之混合樹脂係交聯反應緩慢,無法獲得充分的交聯密度。因此,雖然添
加咪唑系的化合物所代表之環氧樹脂硬化劑已被廣泛所知,但由於環氧樹脂硬化劑係耐熱性低,故而會有起因於孔隙的產生之可靠性低下之疑慮。
本發明係基於上述之情事而完成者,其目的係提供耐熱性高、具有優異的電氣特性且促進環氧樹脂的硬化之熱硬化性樹脂組成物;及由該熱硬化性樹脂組成物所得之成形體及硬化物;以及熱硬化性的接著劑組成物或底部填料組成物。
本發明係一種熱硬化性樹脂組成物,其係含有具下述式(1-a)所示之重複構造單位及下述式(1-b)所示之末端構造之聚合物:
(式中,R1及R2各自獨立地表示氫原子、碳原子數1~4之烷基、苯基或碳原子數3~6之環狀烷基,X表示單鍵或2價的有機基,Y表示2價的有機基);
(式中,Q表示碳原子數1~5之伸烷基、氫原子之至少1個可經鹵素原子取代之伸苯基、或含有至少1個氮原子之5員環或6員環之2價的飽和雜環基,R3表示氫原子或甲基)。
在以前述末端構造之形成時所消耗之咪唑化合物的莫耳數對作為該聚合物之原料化合物(單體)的二胺化合物或雙酚化合物的莫耳數之比所表示者為定義時,前述聚合物之末端為前述式(1-b)所示之末端構造的比例係例如為1mol%~100mol%,較佳為1mol%~50mol%,更佳為5mol%~30mol%。
在前述聚合物之兩末端成為前述式(1-b)所示之末端構造之情況,該聚合物係例如以下述式(1)所表示:
(式中,R1、R2、R3、X及Y與前述式(1-a)中之定義為同義,Q與前述式(1-b)中之定義為同義,k表示1~200之整數)。
前述式(1-b)中,在Q表示含有至少1個氮原子之5員環或6員環之2價的飽和雜環基之情況,作為飽和雜環,可列舉例如哌環、咪唑啶環、吡唑啶環。
前述式(1-b)中,在Q表示碳原子數1~5之伸烷基,且其碳原子數為3~5之情況,前述伸烷基並未限定於直鏈狀,亦可為分枝鏈狀。
前述式(1-a)中,X例如包含表示氫原子之至少1個可經鹵素原子取代之碳原子數1~6之伸烷基、環狀伸烷基、氫原子之至少1個可經鹵素原子取代之伸芳基、磺醯基、羰基、-O-基或-COO-基之2價的有機基。
前述式(1-a)中,X係例如表示以下述式(2)所示之2價的有機基:
(式中,R4及R5各自獨立地表示氫原子、或氫原子之至少1個可經鹵素原子取代之甲基,m表示0或1)。
前述式(2)所示之2價的有機基係例如以下述式(2-a)或式(2-b)所表示:
前述式(1-a)中,Y係例如表示以下述式(3)或式(4)所示之2價的有機基:
(式中,T表示單鍵、磺醯基或-O-基,R7及R8各自獨立地表示氫原子、或氫原子之至少1個可經鹵素原子取代之甲基,2個R6各自獨立地表示氫原子、甲基、乙基或甲氧基,n表示0或1)。
前述式(3)或式(4)所示之2價的有機基係例如以下述式(3-a)、式(4-a)或式(4-b)所表示:
前述聚合物之重量平均分子量係例如為1,000~100,000。
本發明之熱硬化性樹脂組成物可進一步包含環氧樹脂、酚樹脂、溶劑、矽烷耦合劑、及無機填料中之至少1者。
本發明之熱硬化性樹脂組成物係例如為接著劑組成物或底部填料組成物。
本發明之熱硬化性樹脂組成物可在200℃以下的較低溫中硬化,此外,可促進環氧樹脂的硬化反應。由本發明之熱硬化性樹脂組成物所形成之膜係在不產生孔隙之情形下具備良好的接著性,在接著後難以發生剝離,再者,於耐熱性優異之同時,顯示良好的電氣特性。此外,本發明之熱硬化性樹脂組成物係藉由混合環氧樹脂,而提
升交聯密度。從而,本發明之熱硬化性樹脂組成物係有用於作為環氧硬化促進劑、接著劑或底部填料劑。
本發明之熱硬化性樹脂組成物中所含之聚合物係藉由例如在含有將使雙酚化合物、二胺化合物、及醛化合物溶解於溶媒中而成之溶液一面進行加熱、一面進行所定的時間反應而獲得之聚合物的溶液中,添加1分子中具1個胺基或羥基苯基之咪唑化合物、與醛化合物,一面進行加熱、一面進行所定的時間反應而獲得。
在本說明書中,雙酚化合物係指1分子中具2個羥基苯基之化合物,可列舉例如2,2-雙(4-羥基苯基)丙烷〔雙酚A〕、雙(4-羥基苯基)碸〔雙酚S〕、2,2-雙(4-羥基苯基)六氟丙烷〔雙酚AF〕、雙(4-羥基苯基)甲烷〔雙酚F〕、1,1-雙(4-羥基苯基)乙烷〔雙酚E〕、1,3-雙〔2-(4-羥基苯基)-2-丙基〕苯〔雙酚M〕、1,4-雙〔2-(4-羥基苯基)-2-丙基〕苯〔雙酚P〕、2,2’-雙(4-羥基-3-甲基苯基)丙烷、酚酞、4,4’-聯苯酚、1,1-雙(4-羥基苯基)環己烷、1,1-雙(4-羥基-3-甲基苯基)環己烷、9,9-雙(4-羥基苯基)茀、9,9-雙(4-羥基-3-甲基苯基)茀、1,1-雙(3-環己基-4-羥基苯基)環己烷、2,2-雙(3-環己基-4-羥基苯基)丙烷、及2,2-雙(2-羥基-5-聯苯基)丙烷。
作為二胺化合物,可列舉例如4,4’-二胺基-3,3’-二甲
基二苯基甲烷、4,4’-二胺基-3,3’-二乙基二苯基甲烷、4,4’-二胺基-3,3’,5,5’-四甲基二苯基甲烷、鄰聯大茴香胺、鄰苯二胺、間苯二胺、對苯二胺、雙〔4-(3-胺基苯氧基)苯基〕碸、3,3’-磺醯基二苯胺、及4,4’-磺醯基二苯胺。
作為醛化合物,可列舉例如聚甲醛及甲醛。
作為使上述化合物溶解之溶媒,可列舉例如甲苯、二甲苯、二烷、四氫呋喃、氯仿、二氯甲烷、環己酮、環戊酮、甲基乙基酮、及N-甲基-2-吡咯啶酮。
作為1分子中具1個胺基或羥基苯基之咪唑化合物,可列舉例如1-(3-胺基丙基)咪唑、4-(2-甲基-1-咪唑基)苯基胺、4-(1-咪唑基)苯胺、3-氯-4-(1-咪唑基)苯胺、及對(1-咪唑基)苯酚。
在本發明之熱硬化性樹脂組成物含有前述聚合物與環氧樹脂之情況,作為該環氧樹脂,可使用在分子內具至少1個環氧基之化合物。作為此種環氧樹脂,可列舉例如1,4-丁二醇二縮水甘油醚、1,2-環氧基-4-(環氧基乙基)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、1,1,3-參〔對(2,3-環氧基丙氧基)苯基〕丙烷、1,2-環己烷二羧酸二縮水甘油酯、4,4’-亞甲基雙(N,N-二縮水甘油基苯胺)、三羥甲基乙烷三縮水甘油醚、三縮水甘油基對胺基苯酚、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、三聚異氰酸參-(2,3-環氧基丙基)酯、三聚異氰酸單烯丙基二縮水甘油酯、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-環氧基丙氧基全氟異丙基)環己烷、山梨醇聚縮水甘油醚、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、對第三丁基苯基縮水甘油醚、己二酸二縮水甘油醚、鄰酞酸二縮水甘油醚、二溴苯基縮水甘油醚、1,2,7,8-二環氧基辛烷、1,6-二羥甲基全氟己烷二縮水甘油醚、4,4’-雙(2,3-環氧基丙氧基全氟異丙基)二苯醚、2,2-雙(4-縮水甘油基氧基苯基)丙烷、3’,4’-環氧基環己基甲基-3,4-環氧基環己烷羧酸酯、3,4-環氧基環己基環氧乙烷、2-(3,4-環氧基環己基)-3’,4’-環氧基-1,3-二烷-5-螺環己烷、1,2-伸乙基二氧基-雙(3,4-環氧基環己基甲烷)、4’,5’-環氧基-2’-甲基環己基甲基-4,5-環氧基-2-甲基環己烷羧酸酯、乙二醇-雙(3,4-環氧基環己烷羧酸酯)、己二酸雙-(3,4-環氧基環己基甲基)酯、雙(2,3-環氧基環戊基)醚、ε-己內酯變性四(3,4-環氧基環己基甲基)丁烷四羧酸酯、ε-己內酯變性3’,4’-環氧基環己基甲基-3,4-環氧基環己烷羧酸酯、1,2-環氧基-4-乙烯基環己烷、1,2-環氧基-4-(2-
甲基環氧乙基)-1-甲基環己烷、2,2-雙(羥基甲基)-1-丁醇之1,2-環氧基-4-(2-環氧乙基)環己烷加成物、萘型環氧樹脂、環氧化聚丁二烯、甲基丙烯酸3,4-環氧基環己基甲酯、甲基丙烯酸聚縮水甘油酯、苯乙烯-丁二烯嵌段共聚物之環氧化物、及多核苯酚縮水甘油醚衍生樹脂。
上述環氧樹脂可僅使用一種,此外,亦可組合使用二種以上。可使用相對於本發明之熱硬化性樹脂組成物中所含之聚合物而言,1質量%~80質量%、或5質量%~60質量%、或10質量%~50質量%之環氧樹脂。
在本發明之熱硬化性樹脂組成物含有溶劑之情況,作為該溶劑,只要是在半導體裝置製造步驟中可使用之有機溶劑,則無特別限定。作為此種有機溶劑,較佳係使用例如環己酮、環戊酮、四氫呋喃、甲基異戊基酮、2-丁酮、2-庚酮等酮類;乙二醇、乙二醇單醋酸酯、二乙二醇、二乙二醇單醋酸酯、丙二醇、丙二醇單醋酸酯、二丙二醇、二丙二醇單醋酸酯、以及該等之單甲醚、單乙醚、單丙醚、單丁醚、單苯醚等多元醇類及其衍生物;二烷等環式醚類;及乳酸甲酯、乳酸乙酯、醋酸甲酯、醋酸乙酯、醋酸丁酯、丙酮酸甲酯、丙酮酸乙酯、甲氧基丙酸甲酯、乙氧基丙酸乙酯等酯類。此等有機溶劑可僅使用一種,亦可混合使用二種以上。若以自本發明之熱硬化性樹脂組成物去除上述有機溶劑而成之成分作為固形分,則固形分對該組成物之比例係例如為1質量%~70質量%。
本發明之熱硬化性樹脂組成物視需要亦可進
一步含有酚樹脂、無機填料、矽烷耦合劑、界面活性劑、流變調整劑、交聯劑等添加劑。
作為上述酚樹脂,雖然並無特別限定,但可列舉苯酚酚醛清漆、鄰甲酚酚醛清漆等酚類與醛類之酚醛清漆。
作為上述無機填料,可列舉例如粒徑為1nm以上且700nm以下之二氧化矽、氮化鋁、氮化硼、氧化鋯、氧化鋁等之溶膠。該無機填料中所含之粒子亦可利用後述之矽烷耦合劑進行表面處理。
作為上述矽烷耦合劑,可列舉例如乙烯基三甲氧基矽烷、乙烯基三乙氧基矽烷、3-甲基丙烯醯氧基丙基三乙氧基矽烷、3-甲基丙烯醯氧基丙基三甲氧基矽烷、3-縮水甘油基丙基三甲氧基矽烷、3-縮水甘油基丙基三乙氧基矽烷、2-(3,4-環氧基環己基)丙基三甲氧基矽烷、2-(3,4-環氧基環己基)丙基三乙氧基矽烷、2-(3,4-環氧基環己基)乙基三甲氧基矽烷、2-(3,4-環氧基環己基)乙基三乙氧基矽烷、2-(3,4-環氧基環己基)甲基三甲氧基矽烷、2-(3,4-環氧基環己基)甲基三乙氧基矽烷、3-胺基丙基三乙氧基矽烷、3-胺基丙基三甲氧基矽烷、3-苯基胺基丙基三甲氧基矽烷、3-苯基胺基丙基三乙氧基矽烷、3-三乙氧基矽烷基丙基琥珀酸酐、3-三甲氧基矽烷基丙基琥珀酸酐及N-(3-三乙氧基矽烷基丙基)-4,5-二氫咪唑。
作為上述流變調整劑,可列舉例如酞酸二甲
酯、酞酸二乙酯、酞酸二異丁酯、酞酸二己酯、酞酸丁基異癸酯等酞酸衍生物;己二酸二正丁酯、己二酸二異丁酯、己二酸二異辛酯、己二酸辛基癸酯等己二酸衍生物;順丁烯二酸二正丁酯、順丁烯二酸二乙酯、順丁烯二酸二壬酯等順丁烯二酸衍生物;油酸甲酯、油酸丁酯、油酸四氫呋喃甲酯等油酸衍生物;及硬脂酸正丁酯、硬脂酸甘油酯等硬脂酸衍生物。
作為上述界面活性劑,可列舉例如聚氧乙烯月桂基醚、聚氧乙烯硬脂基醚、聚氧乙烯鯨蠟基醚、聚氧乙烯油基醚等聚氧乙烯烷基醚類,聚氧乙烯辛基苯基醚、聚氧乙烯壬基苯基醚等聚氧乙烯烷基芳基醚類,聚氧乙烯/聚氧丙烯嵌段共聚物類,山梨醇酐單月桂酸酯、山梨醇酐單棕櫚酸酯、山梨醇酐單硬脂酸酯、山梨醇酐單油酸酯、山梨醇酐三油酸酯、山梨醇酐三硬脂酸酯等山梨醇酐脂肪酸酯類,聚氧乙烯山梨醇酐單月桂酸酯、聚氧乙烯山梨醇酐單棕櫚酸酯、聚氧乙烯山梨醇酐單硬脂酸酯、聚氧乙烯山梨醇酐三油酸酯、聚氧乙烯山梨醇酐三硬脂酸酯等聚氧乙烯山梨醇酐脂肪酸酯類等之非離子系界面活性劑;EF-TOP(註冊商標)EF301、同EF303、同EF352(三菱材料電子化成(股)製)、Megaface(註冊商標)F171、同F173、同R30、同R30N、同R40、同R40-LM(DIC(股)製)、Fluorad FC430、同FC431(住友3M(股)製)、AsahiGuard(註冊商標)AG710、Surflon(註冊商標)S-382、同SC101、同SC102、同SC103、同SC104、
同SC105、同SC106(旭硝子(股)製)等之氟系界面活性劑;及有機矽氧烷聚合物KP341(信越化學工業(股)製)。此等界面活性劑可僅添加一種,亦可以二種以上之組合進行添加。
雖然本發明之熱硬化性樹脂組成物並非一定需要上述交聯劑,但假若使用,則作為該交聯劑,可列舉例如具有經甲氧基甲基、乙氧基甲基、丁氧基甲基、己氧基甲基等烷氧基甲基或羥基甲基取代之氮原子的含氮化合物。再者,可使用含有酚基之化合物、含有烯丙基之化合物、含有烯丙基之聚合物、含有異氰酸酯基之化合物或含有異氰酸酯基之聚合物作為交聯劑。
作為上述含氮化合物,可列舉例如六甲氧基甲基三聚氰胺、四甲氧基甲基苯并胍胺、1,3,4,6-肆(丁氧基甲基)甘脲、1,3,4,6-肆(羥基甲基)甘脲、1,3-雙(羥基甲基)尿素、1,1,3,3-肆(丁氧基甲基)尿素、1,1,3,3-肆(甲氧基甲基)尿素、1,3-雙(羥基甲基)-4,5-二羥基-2-咪唑啉酮、1,3-雙(甲氧基甲基)-4,5-二甲氧基-2-咪唑啉酮等含氮化合物。作為上述交聯劑,尚可列舉日本Cytec Industries(股)製甲氧基甲基型三聚氰胺化合物(商品名:CYMEL(註冊商標)300、同301、同303、同350)、丁氧基甲基型三聚氰胺化合物(商品名:Mycoat(註冊商標)506、同508)、甘脲化合物(商品名:CYMEL(註冊商標)1170、POWDERLINK(註冊商標)1174)、甲基化尿素樹脂(商品名:
UFR65)、丁基化尿素樹脂(商品名:UFR300、U-VAN10S60、U-VAN10R、U-VAN11HV)、DIC(股)製尿素/甲醛系樹脂(高縮合型,商品名:Beckamine(註冊商標)J-300S、同P-955、同N)之市售的化合物。
上述交聯劑可僅使用一種化合物,此外,亦可組合使用二種以上化合物。可使用相對於本發明之熱硬化性樹脂組成物中所含之聚合物而言,1質量%~50質量%、或8質量%~40質量%、或15質量%~30質量%之交聯劑。
本發明之熱硬化性樹脂組成物可與上述交聯劑同時地含有交聯觸媒。藉由使用交聯觸媒,可促進上述交聯劑之反應。作為交聯觸媒,可列舉例如對甲苯磺酸、三氟甲烷磺酸、甲烷磺酸、對甲苯磺酸吡啶鎓、水楊酸、樟腦磺酸、5-磺酸基水楊酸、檸檬酸、苯甲酸、羥基苯甲酸、4-氯苯磺酸、4-羥基苯磺酸、苯二磺酸及1-萘磺酸。上述交聯觸媒可僅使用一種,此外,亦可組合使用二種以上。可使用相對於本發明之熱硬化性樹脂組成物中所含之聚合物而言,0.01質量%~10質量%、或0.05質量%~8質量%、或0.1質量%~5質量%、或0.3質量%~3質量%、或0.5質量%~1質量%之交聯觸媒。
本發明之熱硬化性樹脂組成物可使用作為接著劑組成物或底部填料組成物。在將本發明之熱硬化性樹脂組成物使用作為接著劑組成物或底部填料組成物之情況,於不損及本發明之本質的特性之範圍內,可進一步含
有具混合性之添加劑,例如用以改良接著劑的性能之加成性樹脂、增黏劑、可塑劑、接著助劑、安定劑、著色劑、消泡材、助熔劑等慣用的添加劑。
作為用以改良接著劑的性能之加成性樹脂(聚合物),可使用聚酯、聚苯乙烯、聚醯亞胺、丙烯酸系聚合物、甲基丙烯酸系聚合物、聚乙烯醚、苯酚酚醛清漆、萘酚酚醛清漆、聚醚、聚醯胺、聚碳酸酯等加成聚合性聚合物或縮聚合性聚合物,較佳係使用具苯環、萘環、蒽環、三環、喹啉環、喹啉環等芳香環之聚合物。作為前述具三環之聚合物,可列舉例如具下述式(5)所示之構造單位之聚酯。
作為如上述之加成性樹脂(聚合物),可列舉例如含有丙烯酸苯甲酯、甲基丙烯酸苯甲酯、丙烯酸苯酯、丙烯酸萘酯、甲基丙烯酸蒽酯、甲基丙烯酸蒽基甲酯、苯乙烯、羥基苯乙烯、苯甲基乙烯基醚、N-苯基順丁烯二醯亞胺等加成聚合性單體作為其構造單位之加成聚合性聚合物;及苯酚酚醛清漆、萘酚酚醛清漆等縮聚合性聚
合物。此外,作為加成性樹脂(聚合物),亦可使用不具芳香環之聚合物。作為此種聚合物,可列舉例如僅含有丙烯酸烷酯、甲基丙烯酸烷酯、乙烯醚、烷基乙烯醚、丙烯腈、順丁烯二醯亞胺、N-烷基順丁烯二醯亞胺、順丁烯二酸酐等不具芳香環之加成聚合性單體作為其構造單位之加成聚合性聚合物。在使用加成聚合性聚合物作為加成性樹脂(聚合物)之情況,該聚合物可為均聚物,亦可為共聚物。
使用了本發明之熱硬化性樹脂組成物的接著劑組成物或底部填料組成物中所添加之加成性樹脂(聚合物)之重量平均分子量係例如為1,000~1,000,000、或3,000~300,000、或5,000~200,000、或10,000~100,000。在本發明之接著劑組成物或底部填料組成物中含有加成性樹脂(聚合物)之情況,作為其含量,係在固形分中例如為40質量%以下,或20質量%以下,或1~19質量%。
上述增黏劑係為了控制彈性率、黏性及表面狀態而進行添加。雖然該種增黏劑之種類較佳係考慮黏性而定,但可列舉例如選自脂肪族系石油樹脂、芳香族系石油樹脂、脂肪族/芳香族共聚系石油樹脂、脂環族系氫化石油樹脂、烷基酚樹脂、二甲苯樹脂、香豆酮-茚樹脂、萜烯樹脂、萜烯酚樹脂、芳香族變性萜烯樹脂、氫化萜烯樹脂、松香系樹脂、氫化松香系樹脂、不均化松香系樹脂、二聚化松香系樹脂、及酯化松香系樹脂中之一種或二
種以上之組合。可以例如相對於本發明之接著劑組成物或底部填料組成物中所含之聚合物而言,100質量%以下,或50質量%以下之比例含有此增黏劑。
以下係基於實施例更詳細地說明本發明,但本發明並非受此等實施例所限定。
以下所記載之合成例中所獲得之聚合物的GPC(gel permeation chromatography,凝膠滲透層析)分析係使用下述之裝置,測定條件係如下述。
裝置:一體型高速GPC系統HLC-8220GPC東曹(股)製
管柱:KF-G、KF-804L
管柱溫度:40℃
溶媒:四氫呋喃(THF)
流量:1.0mL/分鐘
標準試料:聚苯乙烯
檢測器:RI
使4,4’-二胺基-3,3’-二乙基二苯基甲烷(日本化藥(股)製,KAYAHARD A-A)45.79g、雙酚M(三井化學Fine(股)製)69.29g、聚甲醛(東京化成工業(股)製)22.81g及三乙基胺4.05g溶解於N-甲基-2-吡咯啶酮331.18g中後,進行氮置換並使其在90℃進行20小時反
應,而獲得含有聚合物之溶液。然後,冷卻至室溫,在所獲得之溶液中添加1-(3-胺基丙基)咪唑(東京化成工業(股)製)6.26g、聚甲醛(東京化成工業(股)製)6.34g、三乙基胺0.40g及N-甲基-2-吡咯啶酮30.33g後,進行氮置換並使其在90℃進行8小時反應。將進一步獲得之溶液滴至甲醇中,使其再沉澱。然後,以布氏漏斗(Buchner funnel)進行吸引過濾,利用甲醇洗淨2次,使所獲得之粉體以減壓乾燥機進行12小時乾燥,而獲得聚合物。進行所獲得之聚合物的GPC分析,結果利用標準聚苯乙烯換算,重量平均分子量為4,000。另外,可推定所獲得之聚合物具下述式(6-a)所示之重複構造單位及下述式(6-b)所示之末端構造,且該聚合物之末端為下述式(6-b)所示之末端構造的比例係相對於作為原料化合物之雙酚M的莫耳數而言為20mol%。
使1,3-苯二胺(東京化成工業(股)製)1.95g、4,4’-二胺基-3,3’-二乙基二苯基甲烷(日本化藥(股)
製,KAYAHARD A-A)41.20g、雙酚M(三井化學Fine(股)製)69.30g、聚甲醛(東京化成工業(股)製)22.87g及三乙基胺4.05g溶解於N-甲基-2-吡咯啶酮320.48g中後,進行氮置換並使其在90℃進行20小時反應,而獲得含有聚合物之溶液。然後,將所獲得之溶液滴至甲醇中,使其再沉澱。然後,以布氏漏斗進行吸引過濾,利用甲醇洗淨2次,使所獲得之粉體以減壓乾燥機進行12小時乾燥,而獲得聚合物。進行所獲得之聚合物的GPC分析,結果利用標準聚苯乙烯換算,重量平均分子量為9,900。另外,可推定所獲得之聚合物具下述式(6-a)所示之重複構造單位及下述式(7)所示之重複構造單位、以及下述式(8)所示之末端,且不具如上述式(6-b)所示之含有咪唑環之末端構造。
準備作為環氧樹脂硬化劑之1-氰基乙基-2-十一基咪唑(東京化成工業(股)製)。
準備作為環氧樹脂硬化劑之2-乙基-4-甲基咪唑(東京化成工業(股)製)。
準備作為環氧樹脂硬化劑之4-甲基-2-苯基咪唑(東京化成工業(股)製)。
針對合成例1中所獲得之聚合物、以及比較例1~比較例3中所準備之咪唑系的環氧樹脂硬化劑之耐熱性,係經由利用TG-DTA(NETZSCH公司製,TG/DTA2010SR),將試料以10℃/分鐘進行升溫並測定發生5質量%之重量減少的溫度(以下,在本說明書中簡稱為5質量%重量減少溫度)之結果進行評估。將5質量%重量減少溫度之測定結果示於下述表1。
合成例1中所獲得之聚合物的5質量%重量減少溫度成為383℃,相較於比較例1~比較例3中所準備之咪唑系的環氧樹脂硬化劑而言係顯示較高耐熱性。
使合成例1中所獲得之聚合物10g溶解於四氫呋喃40g中,然後,使用孔徑0.2μm的聚四氟乙烯(以下,在本說明書中簡稱為PTFE)製微過濾器進行過濾,而調製含有20質量%固形分之組成物。
使合成例1中所獲得之聚合物5g與作為環氧樹脂之Epolead GT401(Daicel股份有限公司製)5g溶解於四氫呋喃40g中,然後,使用孔徑0.2μm的PTFE製微過濾器進行過濾,而調製含有20質量%固形分之組成物。
使合成例1中所獲得之聚合物50g溶解於環戊酮50g
中,然後,使用孔徑5.0μm的PTFE製微過濾器進行過濾,而調製含有50質量%固形分之組成物。
使合成例1中所獲得之聚合物25g與作為環氧樹脂之Epolead GT401(Daicel股份有限公司製)25g溶解於環戊酮50g中,然後,使用孔徑5.0μm的PTFE製微過濾器進行過濾,而調製含有50質量%固形分之組成物。
使合成例1中所獲得之聚合物3g、作為苯酚酚醛清漆樹脂之KAYAHARD GPH-65(日本化藥(股)製)2g、作為環氧樹脂之Epolead GT401(Daicel股份有限公司製)5g及3-苯基胺基丙基三甲氧基矽烷(東京化成工業(股)製)2g溶解於四氫呋喃65.5g中,然後,混合作為無機填料之有機二氧化矽溶膠〔經3-甲基丙烯醯氧基丙基三甲氧基矽烷表面處理之二氧化矽的甲基乙基酮分散液,前述二氧化矽之一次粒徑40nm~50nm、固形分30.8質量%、比重(20℃)1.007、黏度(20℃)2.5mPa.s、水分0.08質量%〕32.5g,而調製含有20質量%固形分之組成物。
使合成例1中所獲得之聚合物3g、作為苯酚酚醛清
漆樹脂之KAYAHARD GPH-65(日本化藥(股)製)2g、作為環氧樹脂之Epolead GT401(Daicel股份有限公司製)5g、3-苯基胺基丙基三甲氧基矽烷(東京化成工業(股)製)2g溶解於環戊酮22g中,然後,混合作為無機填料之有機二氧化矽溶膠〔經3-甲基丙烯醯氧基丙基三甲氧基矽烷表面處理之二氧化矽的甲基乙基酮分散液,前述二氧化矽之一次粒徑40nm~50nm、固形分30.8質量%、比重(20℃)1.007、黏度(20℃)2.5mPa.s、水分0.08質量%〕32.5g。然後使用蒸發器進行濃縮,而調製含有50質量%固形分之組成物。
使合成例2中所獲得之聚合物5g與作為環氧樹脂之Epolead GT401(Daicel股份有限公司製)5g溶解於四氫呋喃40g中,然後,使用孔徑0.2μm的PTFE製微過濾器進行過濾,而調製含有20質量%固形分之組成物。
使合成例2中所獲得之聚合物25g與作為環氧樹脂之Epolead GT401(Daicel股份有限公司製)25g溶解於環戊酮50g中,然後,使用孔徑5.0μm的PTFE製微過濾器進行過濾,而調製含有50質量%固形分之組成物。
使合成例2中所獲得之聚合物25g、比較例1之1-氰基乙基-2-十一基咪唑0.5g及作為環氧樹脂之Epolead GT401(Daicel股份有限公司製)25.5g溶解於環戊酮51.0g中,然後,使用孔徑5.0μm的PTFE製微過濾器進行過濾,而調製含有50質量%固形分之組成物。
將實施例1、實施例2及實施例5中所調製之組成物1g以及比較例4中所調製之組成物1g置入直徑40mm的金屬製杯中,在50℃進行60分鐘烘烤後,在65℃進行60分鐘烘烤,進而在80℃進行30分鐘烘烤以使四氫呋喃蒸發,而形成熱硬化性的樹脂膜。然後,使用流變計(Anton-Paar公司製,MCR102)以5℃/分鐘進行升溫而評估前述樹脂膜之硬化溫度,若硬化溫度未滿190℃則判斷為○,若為190℃以上則判斷為×。另外,此處所示之硬化溫度係指藉由樹脂膜之硬化反應而使複數黏度成為10,000Pa.s的溫度。將其硬化溫度之結果示於下述表2中。
相較於由比較例4中所調製之組成物所形成之樹脂膜而言,由實施例1、實施例2及實施例5中所調製之組成物所形成之樹脂膜係呈硬化溫度較低的結果,顯示本發明之熱硬化性樹脂組成物促進環氧硬化反應。
將實施例3、實施例4及實施例6中所調製之組成物及比較例6中所調製之組成物在4吋的矽晶圓上以烘烤後的厚度成為15μm~25μm之方式在100℃進行5分鐘烘烤後,在130℃進行5分鐘烘烤以使環戊酮蒸發,而形成熱硬化性的樹脂膜。然後,使用貼合裝置(Ayumi工業(股)製,VJ-300),在真空度10Pa以下、溫度140℃、施加荷重300kg之條件下,使形成有前述樹脂膜之矽晶圓與另一4吋玻璃晶圓進行接著,然後,在180℃進行60分鐘加熱以使樹脂硬化。無孔隙且可良好地接著之情況則評估為○,孔隙存在且發現接著不良之情況則評估為×。將其結果示於下述表3中。
針對在上述接著性之評估中可良好地接著之樣品,在200℃進行5分鐘的加熱後,載置於250℃的加熱板,確認有無剝離產生。於前述加熱板載置該樣品之後即便經過1小時以上仍未產生剝離之情況則評估為○,在未滿1小時便產生剝離之情況則評估為×。將其結果示於下述表
3。
可知實施例3、實施例4及實施例6中所調製之組成物具有良好的接著性與接著後之耐熱性。另一方面,使用了作為既存的環氧樹脂硬化劑之1-氰基乙基-2-十一基咪唑之比較例6中所調製之組成物係耐熱性低,並產生一般認為起因於昇華之孔隙。
將實施例4及實施例6中所調製之組成物以及比較例5及比較例6中所調製之組成物以烘烤後的厚度成為15μm~25μm之方式於層合有鋁箔之矽晶圓上進行旋轉塗佈,在100℃進行5分鐘烘烤後,在130℃進行5分鐘烘烤以使環戊酮蒸發,而獲得積層於鋁箔之熱硬化性的樹脂膜。然後,於氮環境中進而在180℃進行60分鐘烘烤以使樹脂膜硬化後,投入6mol/L的鹽酸水溶液中以使鋁箔溶解,而獲得硬化膜。將所獲得之硬化膜切成寬度5mm,利用熱機械分析(TMA)裝置(NETZSCH公司製,TMA4000SA)測定以5℃/分鐘自室溫升溫至200℃時之
硬化膜的延伸率,藉此評估Tg、Tg前溫度及Tg後溫度的線膨脹係數(CTE)。Tg為140℃以上則判斷為○,未滿140℃則判斷為×;Tg前溫度的CTE未滿70ppm/℃則判斷為○,70ppm/℃以上則判斷為×;Tg後溫度的CTE未滿1000ppm/℃則判斷為○,1000ppm/℃以上則判斷為×。此處所謂的「Tg」係硬化膜之延伸量反曲的溫度。將測定結果示於下述表4中。
由實施例4及實施例6中所調製之組成物所得之硬化膜,環氧樹脂之交聯係充分進展,可獲得良好的硬化膜特性。另一方面,由比較例5及比較例6中所調製之組成物所得之硬化膜,則發生被認為與環氧樹脂間之交聯不充分的特性不良。
在實施例3、實施例4及實施例6中所調製之組成物中添加環戊酮以進行稀釋,在矽晶圓上使用旋轉塗佈機進行塗佈,於加熱板上在100℃進行2分鐘烘烤後,在130
℃進行2分鐘烘烤,進而於經氮置換之烘箱中,在180℃進行60分鐘烘烤,而形成膜厚500nm的硬化膜。對於所製作之樣品,利用CVmap 92B(Four Dimensions公司製)測定施加1MV/cm的電場強度時之洩漏電流密度、及介電率。將其結果示於下述表5中。
可知由實施例3、實施例4及實施例6中所調製之組成物所得之硬化膜,就接著劑或底部填料用途而言,係具有良好的電氣特性。
Claims (12)
- 一種熱硬化性樹脂組成物,其係含有具下述式(1-a)所示之重複構造單位及下述式(1-b)所示之末端構造之聚合物:
- 如請求項1之熱硬化性樹脂組成物,其中,在以前述末端構造之形成時所消耗之咪唑化合物的莫耳數對作為該聚合物之原料化合物的二胺化合物或雙酚化合物的莫耳數之比所表示者為定義時,前述聚合物之末端為前述式(1-b)所示之末端構造的比例為1mol%~100mol%。
- 如請求項1之熱硬化性樹脂組成物,其中,前述式(1-a)中,X表示下述式(2)所示之2價的有機基:
- 如請求項3之熱硬化性樹脂組成物,其中,前述式(2)所示之2價的有機基係以下述式(2-a)或式(2-b)所表示:
- 如請求項1之熱硬化性樹脂組成物,其中,前述式(3)或式(4)所示之2價的有機基係以下述式(3-a)、式(4-a)或式(4-b)所表示:
- 如請求項1之熱硬化性樹脂組成物,其中,前述聚合物之重量平均分子量為1,000~100,000。
- 如請求項1之熱硬化性樹脂組成物,其係進一步包含環氧樹脂。
- 如請求項1之熱硬化性樹脂組成物,其係進一步包含酚樹脂。
- 如請求項1之熱硬化性樹脂組成物,其係進一步包含溶劑。
- 如請求項1之熱硬化性樹脂組成物,其係進一步包含矽烷耦合劑。
- 如請求項1之熱硬化性樹脂組成物,其係進一步包含無機填料。
- 如請求項1之熱硬化性樹脂組成物,其係接著劑 組成物或底部填料組成物。
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