TW202244036A - 感光性樹脂組成物、硬化膜、電子零件、天線元件、半導體封裝及化合物 - Google Patents
感光性樹脂組成物、硬化膜、電子零件、天線元件、半導體封裝及化合物 Download PDFInfo
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Abstract
Description
本發明係關於一種感光性樹脂組成物、硬化膜、電子零件、天線元件、半導體封裝及化合物。更詳細而言,本發明係關於一種可適宜地用於半導體元件等電子零件之表面保護膜或層間絕緣膜、有機電致發光元件之絕緣層等之感光性樹脂組成物。
作為半導體元件之表面保護膜或層間絕緣膜、有機電致元件之絕緣層或薄膜電晶體(TFT,Thin Film Transistor)基板之平坦化膜之代表性材料,可舉例如耐熱性或電氣絕緣性等優異之聚醯亞胺系樹脂。進而,為了提高其生產性,亦對賦予了負型或正型之感光性之聚醯亞胺及其前驅物等進行了研究。
近年來,隨著半導體之用途擴大、性能提高,正致力於藉由製造步驟之效率化來實現成本削減及高積體化。因此,形成多層金屬再配線之半導體裝置備受關注。此種多層金屬再配線之絕緣膜於製造步驟中需要數次高溫處理製程。又,為了提高生產性,要求利用光微影法之圖案加工性。進而,於用於高速無線通信之高頻通信裝置用途中,為了減少傳輸損耗,要求降低絕緣膜之介電損耗因數。因此,要求較高之機械特性、耐熱性、圖案加工性及低介電損耗因數化。作為具有充分之耐熱性之絕緣膜,可舉例如具有聚醯亞胺、聚苯并
唑等樹脂及熱交聯劑之樹脂組成物(專利文獻1)。作為賦予圖案加工性之方法,可舉例如於側鏈導入有特定化學構造之聚醯亞胺前驅物(專利文獻2)。
[先前技術文獻]
[專利文獻]
專利文獻1:日本專利特開2007-16214號公報
專利文獻2:日本專利特開2011-59656號公報
(發明所欲解決之問題)
於應用習知技術作為用於高速無線通信之高頻通信裝置用多層配線絕緣膜之情形時,例如專利文獻1及專利文獻2中所記載之組成物之硬化膜之介電損耗因數的降低並不充分。
(解決問題之技術手段)
為了解決上述課題,本發明係關於以下態樣。
一種感光性樹脂組成物,其係含有(A)多官能單體、(B)黏合劑樹脂及(C)光聚合起始劑者,且該(A)多官能單體含有式(1)所表示之化合物及/或式(2)所表示之化合物,該(B)黏合劑樹脂含有自聚醯亞胺、聚醯亞胺前驅物、聚苯并
唑、聚苯并
唑前驅物、聚醯胺、該等之共聚合體、聚脲、聚酯、聚矽氧烷、丙烯酸系樹脂、酚樹脂及苯并環丁烯樹脂、順丁烯二酸樹脂及環烯烴聚合物所構成之群組選擇之1種以上。
式(1)中,W
1及W
2分別獨立地表示具有碳-碳雙鍵之包含碳數2~25之一價有機基。式(1)中,a、b、c及d分別獨立地為滿足a+b=6~17、c+d=8~19之自然數,虛線部意指碳-碳單鍵或碳-碳雙鍵。
式(2)中,W
3及W
4分別獨立地表示具有碳-碳雙鍵之包含碳數2~25之一價有機基。式(2)中,e、f、g及h分別獨立地為滿足e+f=5~16、g+h=8~19之自然數,虛線部意指碳-碳單鍵或碳-碳雙鍵。
作為用以解決上述課題之另一態樣,本發明係關於如下者。
一種化合物,其係由式(1)表示或由式(2)表示。
式(1)中,W
1及W
2分別獨立地表示式(3)或式(4)所表示之基。式(1)中,a、b、c及d分別獨立地為滿足a+b=6~17、c+d=8~19之自然數,虛線部意指碳-碳單鍵或碳-碳雙鍵。
式(2)中,W
3及W
4分別獨立地表示式(3)或式(4)所表示之基。式(2)中,e、f、g及h分別獨立地為滿足e+f=5~16、g+h=8~19之自然數,虛線部意指碳-碳單鍵或碳-碳雙鍵。
式(3)及式(4)中,X及Y表示-NH-。R
1表示單鍵或包含碳數1~5之二~六價有機基。R
2表示單鍵或包含碳數1~5之二價有機基。i表示1~5之整數。*表示鍵結點。
(對照先前技術之功效)
本發明之感光性樹脂組成物之硬化膜及包含本發明之化合物之組成物之硬化膜的低介電損耗因數優異。
本發明之感光性樹脂組成物含有(A)多官能單體(以下,有時簡稱為(A)成分)、(B)黏合劑樹脂(以下,有時簡稱為(B)成分)及(C)光聚合起始劑(以下,有時簡稱為(C)成分),該(A)成分含有式(1)所表示之化合物及/或式(2)所表示之化合物,該(B)成分含有自聚醯亞胺、聚醯亞胺前驅物、聚苯并
唑、聚苯并
唑前驅物、聚醯胺、該等之共聚合體、聚脲、聚酯、聚矽氧烷、丙烯酸系樹脂、酚樹脂及苯并環丁烯樹脂、順丁烯二酸樹脂及環烯烴聚合物所構成之群組選擇之1種以上。
式(1)中,W
1及W
2分別獨立地表示具有碳-碳雙鍵之包含碳數2~25之一價有機基。式(1)中,a、b、c及d分別獨立地為滿足a+b=6~17、c+d=8~19之自然數,虛線部意指碳-碳單鍵或碳-碳雙鍵。
式(2)中,W
3及W
4分別獨立地表示具有碳-碳雙鍵之包含碳數2~25之一價有機基。式(2)中,e、f、g及h分別獨立地為滿足e+f=5~16、g+h=8~19之自然數,虛線部意指碳-碳單鍵或碳-碳雙鍵。
本發明之感光性樹脂組成物含有(A)成分。藉由包含(A)成分,與上述(C)成分藉由曝光產生之活性種產生交聯反應,可獲得負型圖案。又,使該感光性組成物硬化而成之硬化膜成為低介電係數、低介電損耗因數。
上述(A)成分含有式(1)所表示之化合物及/或式(2)所表示之化合物。式(1)所表示之化合物及/或式(2)所表示之化合物為光聚合性單體,可藉由二聚酸或其衍生物與具有碳-碳雙鍵之化合物之反應而獲得。
二聚酸係藉由不飽和脂肪酸之分子間聚合反應所獲得之已知之二元酸,可藉由使碳數11~22之不飽和脂肪酸二聚化而獲得。關於以工業方式獲得之二聚酸,藉由使油酸或亞麻油酸等碳數18之不飽和脂肪酸二聚化所獲得之碳數36之二元酸為主成分,但根據純化程度,有時會含有任意量之碳數18之單體酸、碳數54之三聚酸及碳數20~54之其他聚合脂肪酸。
作為二聚酸衍生物,可舉例如:將上述二聚酸之所有羧基設為一級羥基之二聚物二醇、設為一級胺基之二聚二胺或設為一級硫醇基之二聚物硫醇及設為異氰酸基之二聚物異氰酸酯。進而可舉例如該等官能基反應所獲得之環氧化合物、氧雜環丁烷化合物。
具有碳-碳雙鍵之化合物進而包含一個能夠與二聚酸衍生物反應之官能基。作為具體之官能基,可舉例如:胺基、羥基、羧基或其鹽之取代基、環氧基、酸酐基或異氰酸基。藉由該等官能基與上述二聚酸或其衍生物所具有之官能基之反應,可獲得式(1)所表示之化合物及/或式(2)所表示之化合物。
作為具有碳-碳雙鍵之化合物,具體而言,可舉例如:N-(4-胺基苯基)順丁烯二醯亞胺、4-胺基苯乙烯、3-胺基苯乙烯、2-胺基苯乙烯、3-胺基-1-丙烯、(甲基)丙烯酸2-羥基乙酯、(甲基)丙烯酸2-羥基丙酯、(甲基)丙烯酸2-羥基丁酯、1-(甲基)丙烯醯氧基-2-丙醇、2-(甲基)丙烯醯胺乙醇、羥甲基乙烯基酮、2-羥乙基乙烯基酮、(甲基)丙烯酸2-羥基-3-甲氧基丙酯、(甲基)丙烯酸2-羥基-3-丁氧基丙酯、(甲基)丙烯酸2-羥基-3-苯氧基丙酯、(甲基)丙烯酸2-羥基-3-第三丁氧基丙酯、(甲基)丙烯酸2-羥基-3-環己基烷氧基丙酯、(甲基)丙烯酸2-羥基-3-環己氧基丙酯、鄰苯二甲酸2-(甲基)丙烯醯氧基乙基-2-羥基丙酯、2-乙烯基苄醇、3-乙烯基苄醇、4-乙烯基苄醇等具有各1個乙烯性不飽和鍵與羥基之醇、甘油-1,3-二(甲基)丙烯酸酯、甘油-1,2-二(甲基)丙烯酸酯、三羥甲基丙烷二(甲基)丙烯酸酯、季戊四醇三(甲基)丙烯酸酯、二季戊四醇五(甲基)丙烯酸酯、甘油-1-烯丙氧基-3-甲基丙烯酸酯、甘油-1-烯丙氧基-2-甲基丙烯酸酯、2-乙基-2-(羥基甲基)丙烷-1,3-二基雙(2-甲基丙烯酸酯)、甲基丙烯酸2-(丙烯醯氧基)-2-(羥基甲基)丁酯等具有2個以上乙烯性不飽和鍵與1個羥基之醇、丙烯酸、甲基丙烯酸、乙烯基乙酸、丁烯酸、衣康酸、順丁烯二酸、反丁烯二酸、肉桂酸及該等之衍生物、丙烯酸酐、甲基丙烯酸酐、衣康酸酐、順丁烯二酸酐、4-戊烯-1,2-二羧酸二酐、5-降
烯-2,3-二羧酸二酐、異氰酸2-丙烯醯氧基乙酯、2-異氰酸甲基丙烯醯氧乙酯或異氰酸1,1-(雙丙烯醯氧基甲基)乙酯等。此處,「(甲基)丙烯酸酯」表示甲基丙烯酸酯或丙烯酸酯。類似之表述亦同樣。
具體而言,二聚酸之市售品可舉例如:HARIDIMER200、HARIDIMER270S(以上為商品名、哈利瑪化成股份有限公司製造)、Td-205(W)、Td-395(以上為商品名、築野食品工業股份有限公司製造)、Pripol1004、Pripol1006、Pripol1009、Pripol1013、Pripol1017、Pripol1040(以上為商品名、Croda Japan股份有限公司製造)。
作為二聚酸衍生物,二聚物二醇之市售品可舉例如:PESPOL HP-1000(商品名、東亞合成股份有限公司製造)、Pripol2023(商品名、Croda Japan股份有限公司製造)。二聚二胺之市售品可舉例如:VERSAMINE551、VERSAMINE552(以上為商品名、BASF Japan股份有限公司)、Priamine1071、Priamine1073、Priamine1074、Priamine1075(以上為商品名、Croda Japan股份有限公司製造)等。
又,從曝光感度之觀點而言,較佳為上述式(1)及上述式(2)中,W
1及W
2之至少一者以及W
3及W
4之至少一者為式(3)、式(4)、式(5)或式(6)所表示之基。
式(3)、式(4)、式(5)及式(6)中,X及Y分別獨立地表示-NH-、-O-、-CH
2-或-S-。R
1表示單鍵或包含碳數1~5之二~六價有機基。R
2表示單鍵或包含碳數1~5之二價有機基。i表示1~5之整數。*表示鍵結點。
上述式(1)及上述式(2)中,作為W
1及W
2之至少一者以及W
3及W
4之至少一者為式(3)、式(4)、式(5)或式(6)所表示之基之(A)成分的具體例,可舉例如式(7)等。
又,從降低介電特性之觀點而言,較佳為上述式(1)及上述式(2)中,W
1及W
2之至少一者以及W
3及W
4之至少一者為式(3)或式(4)所表示之基,且
上述式(3)及上述式(4)中,X及Y為-NH-。
又,更佳為上述式(1)及上述式(2)中,W
1及W
2之至少一者以及W
3及W
4之至少一者為式(8)、式(9)、式(10)或式(11)所表示之基。
*表示鍵結點。
(A)成分較佳為於樹脂組成物中,於5質量%以上且50質量%以下之範圍內製備。
(A)成分之製造方法並無特別限定,可採用加成反應或縮合反應等公知之合成方法。將具體製造方法之一例示於以下。
作為第一步驟,於氮氣環境下將具有一個能夠與碳-碳雙鍵及二聚酸衍生物反應之官能基之化合物投入至反應容器中,並進行攪拌。此時可視需要添加溶劑,又,亦可進而添加反應觸媒或反應促進劑。
作為溶劑,較佳為使用Fedor法中之溶解度參數為10以下者。具體而言,可舉例如甲苯或丙二醇甲醚乙酸酯等,但並不限定於該等。又,亦可含有2種以上之溶劑。
作為反應觸媒,可根據所應用之反應來適當選擇,於羧基與環氧基之反應之情形時,可舉例如:乙酸四丁基銨等銨系觸媒、二甲基苄基胺等胺基系觸媒或三苯基膦等磷系觸媒等,於異氰酸基與胺基或羥基之反應之情形時,可舉例如:二月桂酸二丁基錫等錫化合物或1,4-二雙環[2.2.2]辛烷等三級胺。作為反應促進劑,主要於所應用之反應為羧基與胺基或羥基之縮合反應之情形時需要,可舉例如二環己基碳二亞胺、二異丙基碳二亞胺等,但並不限定於該等。
作為第二步驟,向第一步驟中所製備之攪拌中之溶液中滴加二聚酸衍生物,並進行攪拌直至反應結束。作為二聚酸衍生物,較佳為上述市售品。於反應熱較大之情形時,亦可視需要於滴加時進行冷卻。
作為第三步驟,於反應結束後,藉由利用蒸發器去除製備溶液之溶劑,獲得(A)成分。又,於使用反應觸媒或反應促進劑之情形時,較佳為藉由分液處理或矽膠層析法去除。
本發明中之(A)成分可使用核磁共振裝置(NMR)等鑑定。
NMR為如下分析法:將試料置於較強之磁場中,對使各旋轉方向一致後之分子照射脈衝狀之射頻波,使之核磁共振,其後檢測分子恢復為原本之穩定狀態時所產生之信號,並對分子構造等進行分析。NMR分析中使用最多的是
1H-NMR圖譜,可由峰之化學位移獲得其氫原子所處之環境,由積分值獲得其氫原子之數,由峰之分裂獲得鄰接之質子之影響等與分子構造相關之資訊。作為表示特徵化學位移之例,與烯丙基位之碳鍵結之氫之化學位移於1.5-2 ppm處出現峰值,與烯烴鍵結之氫原子之化學位移於4.5-6 ppm處出現峰值,與芳香環鍵結之氫原子之化學位移於6-9 ppm處出現峰值,與醯胺基鍵結之氫之化學位移於5-11 ppm處出現峰值。
本發明之感光性樹脂組成物含有(B)成分。藉由適當選擇(B)成分,可控制感光性樹脂組成物之特性及使其硬化而成之硬化膜之特性。
上述(B)成分含有自聚醯亞胺、聚醯亞胺前驅物、聚苯并
唑、聚苯并
唑前驅物、聚醯胺、該等之共聚合體、聚脲、聚酯、聚矽氧烷、丙烯酸系樹脂、酚樹脂及苯并環丁烯樹脂、順丁烯二酸樹脂及環烯烴聚合物所構成之群組選擇之1種以上。此處,只要未特別說明,則聚醯胺係指除聚醯亞胺前驅物及聚苯并
唑前驅物以外之聚醯胺。
尤其是從硬化膜之耐熱性、機械特性之觀點而言,上述(B)成分較佳為含有自聚醯亞胺、聚醯亞胺前驅物、聚苯并
唑、聚苯并
唑前驅物、該等之共聚合體及順丁烯二酸樹脂所構成之群組選擇之1種以上。又,上述(B)成分較佳為含有自聚醯亞胺、聚醯亞胺前驅物、聚苯并
唑、聚苯并
唑前驅物及該等之共聚合體所構成之群組選擇之1種以上。
又,從能夠利用鹼性水溶液進行顯影方面而言,較佳為含有自於酸二酐殘基或二胺殘基上具有酚性羥基之聚醯亞胺、聚醯亞胺前驅物及該等之共聚合體所構成之群組選擇之1種以上。
進而從顯影性、低介電損耗因數化之觀點而言,上述(B)成分更佳為含有具有屬於剛直構造之聯苯構造之酚樹脂。該等樹脂亦可組合數種。
作為聚醯亞胺前驅物,可舉例如藉由使四羧酸及其衍生物與二胺及其衍生物反應所獲得者。作為聚醯亞胺前驅物,可舉例如:聚醯胺酸、聚醯胺酸酯、聚醯胺酸醯胺或聚異醯亞胺。
作為四羧酸及其衍生物,可舉例如:1,2,4,5-苯四羧酸(均苯四甲酸)、3,3',4,4'-聯苯四羧酸、2,3,3',4'-聯苯四羧酸、2,2',3,3'-聯苯四羧酸、1,2,5,6-萘四羧酸、1,4,5,8-萘四羧酸、2,3,6,7-萘四羧酸、3,3',4,4'-二苯甲酮四羧酸、2,2',3,3'-二苯甲酮四羧酸、雙(3,4-二羧基苯基)甲烷、雙(2,3-二羧基苯基)甲烷、1,1-雙(3,4-二羧基苯基)乙烷、1,1-雙(2,3-二羧基苯基)乙烷、2,2-雙(3,4-二羧基苯基)丙烷、2,2-雙(2,3-二羧基苯基)丙烷、2,2'-雙[4-(3,4-二羧基苯氧基)苯基]丙烷、2,2-雙(3,4-二羧基苯基)六氟丙烷、2,2-雙(2,3-二羧基苯基)六氟丙烷、雙(3,4-二羧基苯基)碸、雙(3,4-二羧基苯基)醚、2,3,5,6-吡啶四羧酸或3,4,9,10-苝四羧酸、N,N'-雙[5,5'-六氟丙烷-2,2-二基-雙(2-羥基苯基)]雙(3,4-二羧基苯甲醯胺)、雙環[2.2.2]辛-7-烯-2,3,5,6-四羧酸、1,2,4,5-環己烷四羧酸、1,2,3,4-環戊烷四羧酸、1,2,3,4-環丁烷四羧酸或2,3,4,5-四氫呋喃四羧酸、丁烷-1,2,3,4-四羧酸或該等之四羧酸二酐、四羧酸二氯化物或四羧酸活性二酯。該等化合物可單獨使用或組合2種以上使用。
作為二胺及其衍生物,可舉例如:間苯二胺、對苯二胺、3,5-二胺基苯甲酸、4,4'-二胺基聯苯、雙(4-胺基苯氧基)聯苯、2,2'-二甲基-4,4'-二胺基聯苯、2,2'-二乙基-4,4'-二胺基聯苯、3,3'-二甲基-4,4'-二胺基聯苯、3,3'-二乙基-4,4'-二胺基聯苯、2,2',3,3'-四甲基-4,4'-二胺基聯苯、3,3',4,4'-四甲基-4,4'-二胺基聯苯、2,2'-雙(三氟甲基)-4,4'-二胺基聯苯、二巰基苯二胺、1,5-萘二胺、2,6-萘二胺、9,10-蒽二胺、4,4'-二胺基苯甲醯苯胺、3,4'-二胺基二苯醚、4,4'-二胺基二苯醚、3-羧基-4,4'-二胺基二苯醚、3-磺酸-4,4'-二胺基二苯醚、雙[4-(4-胺基苯氧基)苯基]醚、1,4-雙(4-胺基苯氧基)苯、1,3-雙(3-胺基苯氧基)苯、1,3-雙(4-胺基苯氧基)苯、3,4'-二胺基二苯甲烷、4,4'-二胺基二苯甲烷、2,2-雙(4-胺基苯基)六氟丙烷、3,3'-二胺基二苯基碸、3,4'-二胺基二苯基碸、4,4'-二胺基二苯基碸、雙(4-胺基苯氧基苯基)碸、雙(3-胺基苯氧基苯基)碸、2,7-二胺基茀、9,9-雙(4-胺基苯基)茀、2-(4-胺基苯基)-5-胺基苯并
唑、2-(3-胺基苯基)-5-胺基苯并
唑、2-(4-胺基苯基)-6-胺基苯并
唑、2-(3-胺基苯基)-6-胺基苯并
唑、1,4-雙(5-胺基-2-苯并
唑基)苯、1,4-雙(6-胺基-2-苯并
唑基)苯、1,3-雙(5-胺基-2-苯并
唑基)苯、1,3-雙(6-胺基-2-苯并
唑基)苯、2,6-雙(4-胺基苯基)苯并雙
唑、2,6-雙(3-胺基苯基)苯并雙
唑、雙[(3-胺基苯基)-5-苯并
唑基]、雙[(4-胺基苯基)-5-苯并
唑基]、雙[(3-胺基苯基)-6-苯并
唑基]、雙[(4-胺基苯基)-6-苯并
唑基]、3,4'-二胺基二苯硫醚、4,4'-二胺基二苯硫醚、4-胺基苯甲酸4-胺基苯酯、1,3-雙(4-苯胺基)四甲基二矽氧烷、乙二胺、1,3-二胺基丙烷、2-甲基-1,3-丙二胺、1,4-二胺基丁烷、1,5-二胺基戊烷、2-甲基-1,5-二胺基戊烷、1,6-二胺基己烷、1,2-環己二胺、1,4-環己二胺、雙(4-胺基環己基)甲烷、1,7-二胺基庚烷、1,8-二胺基辛烷、1,9-二胺基壬烷、1,10-二胺基癸烷、1,11-二胺基十一烷、1,12-二胺基十二烷或二聚二胺等。尤其從降低介電損耗因數之觀點而言,較佳為二聚二胺。
又,於要求鹼可溶性之用途中,較佳為二胺基酚化合物。作為二胺基酚化合物,可舉例如:雙(3-胺基-4-羥基苯基)醚、雙(3-胺基-4-羥基苯基)甲烷、雙[N-(3-胺基苯甲醯基)-3-胺基-4-羥基苯基]碸、雙[N-(4-胺基苯甲醯基)-3-胺基-4-羥基苯基]碸、雙(3-胺基-4-羥基苯基)碸、雙(3-胺基-4-羥基苯基)丙烷、2,2'-雙[N-(3-胺基苯甲醯基)-3-胺基-4-羥基苯基]丙烷、2,2'-雙[N-(4-胺基苯甲醯基)-3-胺基-4-羥基苯基]丙烷、9,9-雙(3-胺基-4-羥基苯基)茀、9,9-雙[N-(3-胺基苯甲醯基)-3-胺基-4-羥基苯基]茀、9,9-雙[N-(4-胺基苯甲醯基)-3-胺基-4-羥基苯基]茀、N,N'-雙(3-胺基苯甲醯基)-2,5-二胺基-1,4-二羥基苯、N,N'-雙(4-胺基苯甲醯基)-2,5-二胺基-1,4-二羥基苯、N,N'-雙(4-胺基苯甲醯基)-4,4'-二胺基-3,3-二羥基聯苯、N,N'-雙(3-胺基苯甲醯基)-3,3'-二胺基-4,4-二羥基聯苯、N,N'-雙(4-胺基苯甲醯基)-3,3'-二胺基-4,4-二羥基聯苯、3,3'-二胺基-4,4'-聯苯酚、雙(3-胺基-4-羥基苯基)甲烷、1,1-雙(3-胺基-4-羥基苯基)乙烷、2,2-雙(3-胺基-4-羥基苯基)丙烷、2,2-雙(3-胺基-4-羥基苯基)六氟丙烷或2,2-雙[3-(3-胺基苯甲醯胺)-4-羥基苯基]六氟丙烷等。
又,作為具有矽氧烷構造之二胺,可舉例如雙(3-胺基丙基)四甲基二矽氧烷、雙(對胺基苯基)八甲基五矽氧烷,由於可提高與基板之接著性,故較佳。
上述多元胺化合物可直接使用,或用作為胺部位經異氰酸酯化或三甲基矽烷基化之化合物。又,亦可組合該等2種以上之多元胺化合物使用。
又,藉由利用單胺、酸酐、醯氯或單羧酸對樹脂末端進行終止,可調整樹脂之重量平均分子量。
作為單胺之較佳例,可舉例如:5-胺基-8-羥基喹啉、1-羥基-7-胺基萘、1-羥基-6-胺基萘、1-羥基-5-胺基萘、1-羥基-4-胺基萘、2-羥基-7-胺基萘、2-羥基-6-胺基萘、2-羥基-5-胺基萘、1-羧基-7-胺基萘、1-羧基-6-胺基萘、1-羧基-5-胺基萘、2-羧基-7-胺基萘、2-羧基-6-胺基萘、2-羧基-5-胺基萘、2-胺基苯甲酸、3-胺基苯甲酸、4-胺基苯甲酸、4-胺基水楊酸、5-胺基水楊酸、6-胺基水楊酸、3-胺基-4,6-二羥基嘧啶、2-胺基苯酚、3-胺基苯酚、4-胺基苯酚、2-胺基苯硫酚、3-胺基苯硫酚、4-胺基苯硫酚等。亦可使用該等之2種以上。
作為酸酐、醯氯、單羧酸之較佳例,可舉例如:鄰苯二甲酸酐、順丁烯二酸酐、耐地酸酐、環己烷二羧酸酐、3-羥基鄰苯二甲酸酐等酸酐;3-羧基苯酚、4-羧基苯酚、3-羧基苯硫酚、4-羧基苯硫酚、1-羥基-7-羧基萘、1-羥基-6-羧基萘、1-羥基-5-羧基萘、1-巰基-7-羧基萘、1-巰基-6-羧基萘、1-巰基-5-羧基萘等單羧酸類及該等之羧基經醯氯化而成之單醯氯化合物;對苯二甲酸、鄰苯二甲酸、順丁烯二酸、環己烷二羧酸、1,5-二羧基萘、1,6-二羧基萘、1,7-二羧基萘、2,6-二羧基萘等二羧酸類之僅1個羧基經醯氯化而成之單醯氯化合物;藉由單醯氯化合物與N-羥基苯并三唑或N-羥基-5-降
烯-2,3-二羧基醯亞胺之反應所獲得之活性酯化合物。亦可使用該等之2種以上。
作為聚醯亞胺,可舉例如藉由如下方法所獲得者:藉由加熱或使用酸或者鹼等之反應,使上述聚醯胺酸、聚醯胺酸酯、聚醯胺酸醯胺或聚異醯亞胺脫水閉環,且該聚醯亞胺具有四羧酸及/或其衍生物殘基與二胺及/或其衍生物殘基。
聚醯亞胺前驅物為熱硬化性樹脂,藉由在高溫下進行熱硬化而使其脫水閉環,形成高耐熱性之醯亞胺鍵,獲得聚醯亞胺。因此,藉由使樹脂組成物含有具有高耐熱性之醯亞胺鍵之聚醯亞胺,可明顯提高所獲得之硬化膜之耐熱性。因此,適於將硬化膜用於要求高耐熱性之用途之情形時等。又,聚醯亞胺前驅物為於脫水閉環後耐熱性提高之樹脂,故適於用於欲同時實現脫水閉環前之前驅物構造之特性與硬化膜之耐熱性的用途之情形時等。
作為聚醯亞胺,可舉例如含有下述式(12)所表示之構造單位之聚醯亞胺。
式(12)中,R
4表示四~十價有機基,R
5表示二~八價有機基。R
6及R
7表示羥基或碳數1~20之有機基,可分別為單一者,亦可混合存在不同者。j及k表示0~6之整數。R
4-(R
6)
j表示上述四羧酸及/或其衍生物殘基。R
5-(R
7)
k表示上述二胺及/或其衍生物殘基。尤其是從低介電損耗因數化之觀點而言,較佳為二聚二胺殘基。*表示鍵結點。
作為聚醯亞胺前驅物,較佳為聚醯胺酸或聚醯胺酸酯,可舉例如含有式(13)所表示之構造單位之聚醯亞胺前驅物。
式(13)中,R
8表示四~六價有機基,R
9表示二~十價有機基。數個R
11分別獨立地表示碳數1~10之有機基或羥基,n表示0~8之整數。數個R
10可相同亦可不同,表示氫原子或碳數1~30之一價烴基。m表示2~4之整數。R
8-(COOR
10)
m表示上述四羧酸及/或其衍生物殘基。R
9-(R
11)
n表示上述二胺及/或其衍生物殘基。尤其是從低介電損耗因數化之觀點而言,較佳為二聚二胺殘基。又,從對鹼性水溶液之可溶性之觀點而言,較佳為二胺基苯酚殘基,尤佳為2,2-雙(3-胺基-4-羥基苯基)六氟丙烷殘基或2,2-雙[3-(3-胺基苯甲醯胺)-4-羥基苯基]六氟丙烷殘基。*表示鍵結點。
又,關於R
10,於表示碳數1~30之有機基時,具體而言,R
10表示四羧酸二酯殘基。作為四羧酸二酯之生成方法,亦可使其直接於酸二酐及醇溶劑中反應,但從反應性之觀點而言,較佳為使用反應活化劑。作為反應活性劑,可舉例如:吡啶、二甲胺基吡啶、三乙基胺、N-甲基
啉、1,8-二氮雜雙環十一烯等三級胺。作為反應活化劑之添加量,相對於反應之酸酐基,較佳為3 mol%以上且300 mol%以下,更佳為20 mol%以上且150 mol%以下。又,為了防止乙烯性不飽和鍵部位於反應中交聯,亦可使用少量聚合抑制劑。藉此,於反應性較低之具有乙烯性不飽和鍵之醇類與四羧酸二酐之反應中,於120℃以下之範圍內加熱,可促進反應。作為聚合抑制劑,可舉例如:對苯二酚、4-甲氧基苯酚、第三丁基兒茶酚、雙第三丁基羥基甲苯等酚化合物。作為聚合抑制劑之添加量,相對於醇類之乙烯性不飽和鍵,聚合抑制劑之酚性羥基較佳為0.1 mol%以上且5 mol%以下。
作為上述具有乙烯性不飽和鍵之醇類,可舉例如具有羥基之(甲基)丙烯酸酯或不飽和脂肪酸改質醇。作為具有羥基之(甲基)丙烯酸酯,可舉例如:(甲基)丙烯酸2-羥基乙酯、(甲基)丙烯酸2-羥基丙酯、(甲基)丙烯酸2-羥基丁酯、1-(甲基)丙烯醯氧基-2-丙醇、2-(甲基)丙烯醯胺乙醇、羥甲基乙烯基酮、2-羥乙基乙烯基酮、(甲基)丙烯酸2-羥基-3-甲氧基丙酯、(甲基)丙烯酸2-羥基-3-丁氧基丙酯、(甲基)丙烯酸2-羥基-3-苯氧基丙酯、(甲基)丙烯酸2-羥基-3-第三丁氧基丙酯、(甲基)丙烯酸2-羥基-3-環己基烷氧基丙酯、(甲基)丙烯酸2-羥基-3-環己氧基丙酯、鄰苯二甲酸2-(甲基)丙烯醯氧基乙基-2-羥基丙酯等具有各1個乙烯性不飽和鍵與羥基之醇、甘油-1,3-二(甲基)丙烯酸酯、甘油-1,2-二(甲基)丙烯酸酯、三羥甲基丙烷二(甲基)丙烯酸酯、季戊四醇三(甲基)丙烯酸酯、二季戊四醇五(甲基)丙烯酸酯、甘油-1-烯丙氧基-3-甲基丙烯酸酯、甘油-1-烯丙氧基-2-甲基丙烯酸酯、2-乙基-2-(羥基甲基)丙烷-1,3-二基雙(2-甲基丙烯酸酯)、甲基丙烯酸2-(丙烯醯氧基)-2-(羥基甲基)丁酯等具有2個以上乙烯性不飽和鍵與1個羥基之醇等。
作為不飽和脂肪酸改質醇,可舉例如碳數6以上之不飽和脂肪酸改質醇。從曝光感度之觀點而言,較佳為於末端具有不飽和基、或具有順式構造之雙鍵之醇,從介電係數、介電損耗因數之觀點而言,較佳為碳數12以上。作為不飽和脂肪酸改質醇之具體例,可舉例如:5-己烯-1-醇、3-己烯-1-醇、6-庚烯-1-醇、順式-5-辛烯-1-醇、順式-3-辛烯-1-醇、順式-3-壬烯-1-醇、順式-6-壬烯-1-醇、9-癸烷-1-醇、順式-4-癸烷-1-醇、10-十一烯-1-醇、11-十二烷-1-醇、反式亞油醇、油醇、亞麻醇、次亞麻醇及瓢兒菜醇等。該等中,從所獲得之硬化膜之介電特性與曝光感度之觀點而言,較佳為油醇、亞麻醇、次亞麻醇。
於使酸酐與具有乙烯性不飽和鍵之醇類反應時,亦可同時使用其他醇。其他醇可根據曝光感度之調整、於有機溶劑中之溶解性之調整等各種目的來適當選擇。具體而言,可舉例如:甲醇、乙醇、1-丙醇、2-丙醇、1-丁醇、2-丁醇、異丁醇、第三丁醇、1-戊醇、2-戊醇、3-戊醇、異戊醇等脂肪族醇或乙二醇單甲醚、乙二醇單乙醚、乙二醇單丁醚、二乙二醇單甲醚、二乙二醇單乙醚、二乙二醇單丁醚、三乙二醇單甲醚、三乙二醇單乙醚、三乙二醇單丁醚、丙二醇單甲醚、丙二醇單乙醚、丙二醇單丁醚、二丙二醇單甲醚、二丙二醇單乙醚、二丙二醇單丁醚、三丙二醇單甲醚、三丙二醇單乙醚、三丙二醇單丁醚等來自環氧烷之一元醇等。
作為二羧酸之例,可舉例如:對苯二甲酸、間苯二甲酸、二聚酸、二苯醚二羧酸、雙(羧基苯基)六氟丙烷、聯苯二羧酸、二苯甲酮二羧酸、三苯基二羧酸等;作為三羧酸之例,可舉例如:偏苯三甲酸、1,3,5-苯三甲酸、二苯醚三羧酸、聯苯基三羧酸等。該等化合物可單獨使用或組合2種以上使用。尤其是從降低介電損耗因數之觀點而言,較佳為二聚酸。
作為二胺基苯酚之例,可舉例如於聚醯亞胺前驅物中所例示之二胺基酚化合物。
聚苯并
唑前驅物為熱硬化性樹脂,藉由在高溫下進行熱硬化而使其脫水閉環,形成高耐熱性且剛直之苯并
唑環,獲得聚苯并
唑。因此,藉由使樹脂組成物含有具有高耐熱性且剛直之苯并
唑環之聚苯并
唑,可明顯提高所獲得之硬化膜之耐熱性。因此,適於將硬化膜用於要求高耐熱性之用途之情形時等。又,由於聚苯并
唑前驅物為於脫水閉環後耐熱性提高之樹脂,故適於用於欲同時實現脫水閉環前之前驅物構造之特性與硬化膜之耐熱性的用途之情形時等。
作為聚苯并
唑,可舉例如:藉由使二羧酸與作為二胺之二胺基酚化合物藉由使用多磷酸之反應進行脫水閉環所獲得者;或藉由使作為聚苯并
唑前驅物之例如上述多羥基醯胺藉由加熱、或使用無水磷酸、鹼或碳二醯亞胺化合物等之反應進行脫水閉環所獲得者。
式(14)中,R
12表示二~六價有機基,R
13表示四~六價有機基。R
14及R
15分別獨立地表示碳數1~10之有機基或羥基。o表示0~4之整數,p表示0~2之整數。R
12-(R
14)
o表示上述二羧酸及/或其衍生物殘基。尤其是從低介電損耗因數化之觀點而言,較佳為二聚酸殘基。R
1 3-(R
15)
p表示上述二胺基酚化合物及/或其衍生物殘基。*表示鍵結點。
式(15)中,R
16表示二~六價有機基,R
17表示單鍵或二~六價有機基。R
18及R
19表示碳數1~10之有機基或羥基。q及r表示0~4之整數。R
1 6-(R
18)
q表示上述二羧酸及/或其衍生物殘基。尤其是從低介電損耗因數化之觀點而言,較佳為二聚酸殘基。R
17-(R
19)
r表示上述二胺基酚化合物及/或其衍生物殘基。*表示鍵結點。
作為聚醯胺,可舉例如藉由使二羧酸與二胺化合物藉由使用多磷酸之反應進行脫水縮合所獲得者。
作為聚醯胺,可舉例如含有下述式(16)所表示之構造單位者。
式(16)中,R
20及R
21表示二~六價有機基。R
22及R
23分別獨立地表示碳數1~10之有機基或羥基。t表示0~4之整數,u表示0~4之整數。R
20-(R
22)
t表示上述二羧酸及/或其衍生物殘基,R
21-(R
23)
u表示除上述二胺基酚化合物以外之二胺化合物及/或其衍生物殘基。*表示鍵結點。
作為聚脲,可舉例如二胺與多官能異氰酸酯之複加成反應中所獲得者。
作為多官能異氰酸酯,可舉例如:六亞甲基二異氰酸酯、1,3-雙(異氰酸基甲基)苯、1,3-雙(異氰酸基甲基)環己烷、降
烯二異氰酸酯、萘-1,5-二異氰酸酯、二苯甲烷-4,4'-二異氰酸酯或甲苯-2,4-二異氰酸酯等,作為多元醇,可舉例如:乙二醇、丙二醇、季戊四醇、二季戊四醇、1,4-雙(2-羥基乙氧基)苯、1,3-雙(2-羥基乙氧基)苯、4,4'-雙(2-羥基乙氧基)聯苯、2,2-雙(4-(2-羥基乙氧基)苯基)丙烷或雙(4-(2-羥基乙氧基)苯基)甲烷等。
二胺與多官能異氰酸酯之複加成反應物可為無觸媒,但亦可使用觸媒。作為觸媒,可舉例如二月桂酸二丁基錫等錫化合物或1,4-二氮雜雙環[2.2.2]辛烷等三級胺。
作為聚酯,經過多元醇化合物與酸二酐之複加成反應所獲得者由於合成容易,且副反應較少,故較佳。作為多元醇化合物,由於容易導入自由基聚合性基及芳香環,故較佳為藉由多官能環氧化合物與(甲基)丙烯酸等含自由基聚合性基一元酸化合物之反應所獲得者。
作為多官能環氧化合物,可舉例如:乙二醇二環氧丙醚、新戊二醇二環氧丙醚或氫化雙酚A二環氧丙醚等脂肪族環氧化合物、或氫化雙酚A二環氧丙醚或9,9-雙(4-縮水甘油醚氧基苯基)茀等芳香族環氧化合物,但並不限定於該等。
又,作為其他多元醇化合物,可舉例如:乙二醇、丙二醇、丁二醇、甘油、三羥甲基丙烷或季戊四醇等脂肪族醇化合物或9,9-雙[4-(2-羥基乙氧基)苯基]茀等。
作為上述酸二酐,可舉例如於聚醯亞胺前驅物之說明中所例示之四羧酸二酐。
作為聚矽氧烷,可舉例如使用至少1種有機矽烷化合物之水解縮合物。作為有機矽烷化合物,可舉例如:四甲氧基矽烷、四乙氧基矽烷、四乙醯氧基矽烷、四苯氧基矽烷等4官能性矽烷;甲基三甲氧基矽烷、甲基三乙氧基矽烷、甲基三異丙氧基矽烷、甲基三正丁氧基矽烷、乙基三甲氧基矽烷、乙基三乙氧基矽烷、乙基三異丙氧基矽烷、乙基三正丁氧基矽烷、正丙基三甲氧基矽烷、正丙基三乙氧基矽烷、正丁基三甲氧基矽烷、正丁基三乙氧基矽烷、正己基三甲氧基矽烷、正己基三乙氧基矽烷、癸基三甲氧基矽烷、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甲氧基矽烷、3-甲基丙烯醯氧基丙基三乙氧基矽烷、3-丙烯醯氧基丙基三甲氧基矽烷、苯基三甲氧基矽烷、苯基三乙氧基矽烷、對羥基苯基三甲氧基矽烷、1-(對羥基苯基)乙基三甲氧基矽烷、2-(對羥基苯基)乙基三甲氧基矽烷、4-羥基-5-(對羥基苯基羰氧基)戊基三甲氧基矽烷、三氟甲基三甲氧基矽烷、三氟甲基三乙氧基矽烷、3,3,3-三氟丙基三甲氧基矽烷、3-胺基丙基三甲氧基矽烷、3-胺基丙基三乙氧基矽烷、3-縮水甘油氧基丙基三甲氧基矽烷、3-縮水甘油氧基丙基三乙氧基矽烷、2-(3,4-環氧環己基)乙基三甲氧基矽烷、2-(3,4-環氧環己基)乙基三乙氧基矽烷、[(3-乙基-3-氧雜環丁基)甲氧基]丙基三甲氧基矽烷、[(3-乙基-3-氧雜環丁基)甲氧基]丙基三乙氧基矽烷、3-巰基丙基三甲氧基矽烷、3-三甲氧基矽烷基丙基琥珀酸、1-萘基三甲氧基矽烷、1-萘基三乙氧基矽烷、1-萘基三正丙氧基矽烷、2-萘基三甲氧基矽烷、1-蒽基三甲氧基矽烷、9-蒽基三甲氧基矽烷、9-菲基三甲氧基矽烷、9-茀基三甲氧基矽烷、2-茀基三甲氧基矽烷、1-芘基三甲氧基矽烷、2-茚基三甲氧基矽烷、5-二氫苊基三甲氧基矽烷等3官能性矽烷;二甲基二甲氧基矽烷、二甲基二乙氧基矽烷、二甲基二乙醯氧基矽烷、二正丁基二甲氧基矽烷、二苯基二甲氧基矽烷、(3-縮水甘油氧基丙基)甲基二甲氧基矽烷、(3-縮水甘油氧基丙基)甲基二乙氧基矽烷、二(1-萘基)二甲氧基矽烷、二(1-萘基)二乙氧基矽烷等2官能性矽烷;三甲基甲氧基矽烷、三正丁基乙氧基矽烷、(3-縮水甘油氧基丙基)二甲基甲氧基矽烷、(3-縮水甘油氧基丙基)二甲基乙氧基矽烷等1官能性矽烷。亦可使用該等有機矽烷之2種以上。
有機矽烷化合物之水解反應條件只要適當設定即可,例如較佳為於溶劑中,歷時1~180分鐘於有機矽烷化合物中添加酸觸媒及水後,於室溫~110℃下進行1~180分鐘反應。藉由在此種條件下進行水解反應,可抑制急遽之反應。反應溫度較佳為30~105℃。
又,水解反應較佳為在酸觸媒之存在下進行。作為酸觸媒,較佳為包含甲酸、乙酸或磷酸之酸性水溶液。相對於水解反應時所使用之全部有機矽烷化合物100質量份,該等酸觸媒之含量較佳為0.1~5質量份。藉由將酸觸媒之含量設為上述範圍,能夠以水解反應必要且充分地進行之方式容易地控制。
作為縮合反應之條件,較佳為於藉由有機矽烷化合物之水解反應獲得矽烷醇化合物後,直接以50℃~溶劑之沸點將反應液加熱1~100小時。又,為了提高聚矽氧烷之聚合度,亦可再加熱或添加鹼觸媒。又,亦可視需要於水解反應後,藉由加熱及/或減壓將生成醇等適量餾出、去除,其後添加任意溶劑。
作為丙烯酸系樹脂,可舉例如使(甲基)丙烯酸、(甲基)丙烯酸酯進行自由基聚合而成者等。其中,從圖案加工性之觀點而言,較佳為含羧基之丙烯酸系樹脂,從硬化膜硬度方面出發,較佳為於至少一部分中導入有乙烯性不飽和雙鍵基。
作為丙烯酸系樹脂之合成方法,可舉例如(甲基)丙烯酸化合物之自由基聚合。作為(甲基)丙烯酸化合物,可舉例如羧基及/或含酸酐基(甲基)丙烯酸化合物或其他(甲基)丙烯酸酯。作為自由基聚合之觸媒,通常使用偶氮二異丁腈等偶氮化合物或過氧化苯甲醯等有機過氧化物。
自由基聚合之條件只要適當設定即可,較佳為於溶劑中,添加羧基及/或含酸酐基(甲基)丙烯酸化合物、其他(甲基)丙烯酸酯及自由基聚合觸媒,藉由通入氮氣或減壓脫氣等對反應容器內充分地進行氮氣置換後,於60~110℃下進行30~300分鐘反應。於使用含酸酐基(甲基)丙烯酸化合物之情形時,較佳為添加理論量之水於30~60℃下進行30~60分鐘反應。又,亦可視需要使用硫醇化合物等鏈轉移劑。
作為(甲基)丙烯酸酯,可使用(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸丙酯、(甲基)丙烯酸環丙酯、(甲基)丙烯酸環戊酯、(甲基)丙烯酸環己酯、(甲基)丙烯酸環己烯酯、(甲基)丙烯酸4-甲氧基環己酯、(甲基)丙烯酸2-環丙氧基羰基乙酯、(甲基)丙烯酸2-環戊氧基羰基乙酯、(甲基)丙烯酸2-環己氧基羰基乙酯、(甲基)丙烯酸2-環己烯氧基羰基乙酯、(甲基)丙烯酸2-(4-甲氧基環己基)氧基羰基乙酯、(甲基)丙烯酸降
酯、(甲基)丙烯酸異
酯、(甲基)丙烯酸四環癸酯、(甲基)丙烯酸二環戊烯酯、(甲基)丙烯酸金剛烷基酯、(甲基)丙烯酸2-甲基金剛烷基酯、(甲基)丙烯酸1-甲基金剛烷基酯等。
又,丙烯酸系樹脂亦可為(甲基)丙烯酸化合物與其他含不飽和雙鍵單體之共聚合體。作為其他含不飽和雙鍵單體,可舉例如:苯乙烯、對甲基苯乙烯、鄰甲基苯乙烯、間甲基苯乙烯、α-甲基苯乙烯、對羥基苯乙烯、順丁烯二酸酐、降
烯、降
烯二羧酸、降
烯二羧酸酐、環己烯、丁基乙烯醚、丁基烯丙醚、2-羥乙基乙烯醚、2-羥乙基烯丙醚、環己烷乙烯醚、環己烷烯丙醚、4-羥丁基乙烯醚。
作為具有乙烯性不飽和鍵之丙烯酸系樹脂,較佳為使羧基及/或含酸酐基(甲基)丙烯酸化合物、(甲基)丙烯酸酯及/或其他含不飽和雙鍵單體進行自由基聚合後,使具有乙烯性不飽和雙鍵基之環氧化合物進行加成反應所獲得者。作為加成反應中所使用之觸媒,可舉例如:二甲基苯胺、2,4,6-參(二甲基胺基甲基)苯酚或二甲基苄基胺等胺基系觸媒;三苯基膦等磷系觸媒;乙酸四丁基銨等銨系觸媒或乙醯丙酮酸鉻或氯化鉻等鉻系觸媒等。
作為具有乙烯性不飽和雙鍵基之環氧化合物,可舉例如:(甲基)丙烯酸縮水甘油酯、(甲基)丙烯酸α-乙基環氧丙酯、(甲基)丙烯酸α-正丙基環氧丙酯、(甲基)丙烯酸α-正丁基環氧丙酯、(甲基)丙烯酸3,4-環氧丁酯、(甲基)丙烯酸3,4-環氧庚酯、(甲基)丙烯酸α-乙基-6,7-環氧庚酯、丁基乙烯醚、丁基烯丙醚、2-羥乙基乙烯醚、2-羥乙基烯丙醚、環己烷乙烯醚、環己烷烯丙醚、4-羥丁基乙烯醚、4-羥丁基烯丙醚、烯丙基環氧丙醚、乙烯基環氧丙醚、鄰乙烯基苄基環氧丙醚、間乙烯基苄基環氧丙醚、對乙烯基苄基環氧丙醚、α-甲基-鄰乙烯基苄基環氧丙醚、α-甲基-間乙烯基苄基環氧丙醚、α-甲基-對乙烯基苄基環氧丙醚、2,3-二縮水甘油氧基甲基苯乙烯、2,4-二縮水甘油氧基甲基苯乙烯、2,5-二縮水甘油氧基甲基苯乙烯、2,6-二縮水甘油氧基甲基苯乙烯、2,3,4-三縮水甘油氧基甲基苯乙烯、2,3,5-三縮水甘油氧基甲基苯乙烯、2,3,6-三縮水甘油氧基甲基苯乙烯、3,4,5-三縮水甘油氧基甲基苯乙烯或2,4,6-三縮水甘油氧基甲基苯乙烯等。
作為酚樹脂,存在酚醛清漆樹脂或可溶酚醛樹脂,可藉由使用各種酚類單獨獲得,或使該等之混合物與福馬林等醛類進行縮聚而獲得。
作為構成酚醛清漆樹脂及可溶酚醛樹脂之酚類,可舉例如:苯酚、對甲酚、間甲酚、鄰甲酚、2,3-二甲基苯酚、2,4-二甲基苯酚、2,5-二甲基苯酚、2,6-二甲基苯酚、3,4-二甲基苯酚、3,5-二甲基苯酚、2,3,4-三甲基苯酚、2,3,5-三甲基苯酚、3,4,5-三甲基苯酚、2,4,5-三甲基苯酚、亞甲基雙酚、亞甲基雙對甲酚、間苯二酚、兒茶酚、2-甲基間苯二酚、4-甲基間苯二酚、鄰氯苯酚、間氯苯酚、對氯苯酚、2,3-二氯苯酚、間甲氧基苯酚、對甲氧基苯酚、對丁氧基苯酚、鄰乙基苯酚、間乙基苯酚、對乙基苯酚、2,3-二乙基苯酚、2,5-二乙基苯酚、對異丙基苯酚、對苯基苯酚、α-萘酚、β-萘酚等,該等可單獨使用,或以該等之混合物之形式使用。
又,作為用於和酚醛清漆樹脂或可溶酚醛樹脂進行縮聚之醛類,除了福馬林以外,還可舉例如:多聚甲醛、乙醛、苯甲醛、羥基苯甲醛、氯乙醛等,該等可單獨使用或以該等之混合物之形式使用。
又,酚樹脂亦可為對加成於芳香族環之氫原子之一部分利用碳數1~20之烷基、氟烷基、羥基、烷氧基、烷氧基甲基、羥甲基、羧基、酯基、硝基、氰基、氟原子、或氯原子中之任1種以上進行取代而成之構造等。
尤其是從低介電損耗因數化之觀點而言,更佳為具有剛直之萘構造或聯苯構造之酚醛清漆樹脂或可溶酚醛樹脂,具體而言,作為酚,較佳為使用對苯基苯酚、α-萘酚或β-萘酚。又,作為市售品之酚樹脂,可舉例如:PN-80、PN-100、GPH-65、GPH-103(以上為商品名、日本化藥股份有限公司製造)、XLC-3L(商品名、三井化學股份有限公司製造)、MEHC-7851SS(商品名、明和化成股份有限公司製造)等,尤佳為具有剛直構造之GPH-65、GPH-103及MEHC-7851SS等。
作為苯并環丁烯樹脂,例如係藉由使溴化芳基環丁烯化合物與含有不飽和烷基之化合物於鈀觸媒存在下反應而製造。具體而言,可舉例如二乙烯基矽氧烷雙苯并環丁烯等。又,作為市售品之苯并環丁烯化合物,可舉例如CYCLOTENE3022-63或4026-46(以上為商品名、陶氏化學股份有限公司製造)等。
作為順丁烯二酸樹脂,例如係藉由使順丁烯二酸酐或順丁烯二酸酯與含有不飽和烷基之化合物於自由基聚合觸媒下共聚合而製造。具體而言,可舉例如苯乙烯順丁烯二酸酐共聚合體或順丁烯二酸酐改質聚乙烯等。又,作為市售品之順丁烯二酸樹脂,可舉例如:XIRAN1000、XIRAN1440、XIRAN2000、XIRAN2500、XIRAN3000、XIRAN3500、XIRAN4000、XIRAN6000及XIRAN9000(以上為商品名、巴工業股份有限公司製造)等。
作為環烯烴聚合物,例如可藉由使降
烯氫化開環複分解聚合來製造,或亦可藉由使降
烯與含有不飽和烷基化合物於自由基聚合觸媒下加成聚合後進行氫化等來製造。作為市售品,可舉例如APL系列(商品名、三井化學股份有限公司)。
樹脂組成物中,關於(B)成分之含量,相對於(A)成分100質量份,為了形成膜厚1 μm以上之塗佈膜,較佳為含有10質量份以上,且為了充分地降低所獲得之硬化膜之介電損耗因數,較佳為含有500質量份以下。
本發明之感光性樹脂組成物含有(C)成分。藉由含有(C)成分,產生曝光時開始(A)成分之交聯反應之活性種,且經過後續之顯影步驟,能夠進行圖案加工。(C)成分只要為藉由曝光產生自由基之化合物,則並無特別限制,烷基苯酮化合物、胺基二苯甲酮化合物、二酮化合物、酮酯化合物、氧化膦化合物、肟酯化合物及苯甲酸酯化合物由於感度、穩定性、合成容易性優異,故較佳。其中,從感度之觀點而言,較佳為烷基苯酮化合物、肟酯化合物,尤佳為肟酯化合物。又,於加工膜厚為5 μm以上之厚膜之情形時,從解像度之觀點而言,較佳為氧化膦化合物。
作為烷基苯酮化合物,可含有公知者。可舉例如:2-甲基-[4-(甲硫基)苯基]-2-
啉基丙烷-1-酮、2-二甲基胺基-2-(4-甲基苄基)-1-(4-
啉-4-基-苯基)-丁烷-1-酮或2-苄基-2-二甲基胺基-1-(4-
啉基苯基)-丁酮-1等α-胺基烷基苯酮化合物;2-羥基-2-甲基-1-苯基丙烷-1-酮等α-羥基烷基苯酮化合物;4-苯甲醯基-4-甲基苯基酮等α-烷氧基烷基苯酮化合物;對第三丁基二氯苯乙酮等苯乙酮化合物。
該等之中,2-甲基-[4-(甲硫基)苯基]-2-
啉基丙烷-1-酮、2-二甲基胺基-2-(4-甲基苄基)-1-(4-
啉-4-基-苯基)-丁烷-1-酮或2-苄基-2-二甲基胺基-1-(4-
啉基苯基)-丁酮-1等α-胺基烷基苯酮化合物由於感度較高,故較佳。
作為氧化膦化合物,可含有公知者。可舉例如:6-三甲基苯甲醯基苯基氧化膦、雙(2,4,6-三甲基苯甲醯基)苯基氧化膦、雙(2,6-二甲氧基苯甲醯基)-(2,4,4-三甲基戊基)氧化膦。
作為肟酯化合物,可舉例如:1-苯基-1,2-丙二酮-2-(鄰乙氧基羰基)肟、1-[9-乙基-6-(2-甲基苯甲醯基)-9H-咔唑-3-基]-,1-(O-乙醯肟)、NCI-831、NCI-930(以上為ADEKA股份有限公司製造)、OXE-03、OXE-04(以上為BASF股份有限公司製造)等。
該等之中,從感度之觀點而言,較佳為1-[9-乙基-6-(2-甲基苯甲醯基)-9H-咔唑-3-基]-,1-(O-乙醯肟)、2-辛二酮,1-[4-(苯硫基)-2-(O-苯甲醯基肟)]、NCI-831、NCI-930、OXE-03、OXE-04。
作為胺基二苯甲酮化合物,可含有公知者。可舉例如4,4-雙(二甲基胺基)二苯甲酮等。
作為二酮化合物,可舉例如苯偶姻等公知者。
作為酮酯化合物,可舉例如苯甲醯基甲酸甲酯、苯甲醯基甲酸乙酯等公知者。
作為苯甲酸酯化合物,可舉例如:鄰苯甲醯苯甲酸甲酯、對二甲基胺基苯甲酸乙酯、4-(二甲基胺基)苯甲酸2-乙基己酯等公知者。
作為上述(C)成分之其他具體例,可舉例如:三苯基膦、四溴化碳、三溴苯基碸等公知者。
作為(C)成分之含量,於將(A)成分與(B)成分之和設為100質量份之情形時,由於0.5質量份以上且20質量份以下可獲得充分之感度,且可抑制熱硬化時之脫氣量,故較佳。其中,更佳為1.0質量部以上且10質量份以下。
為了提高(C)成分之功能,亦可包含增感劑。藉由含有增感劑,能夠提高感度或調整感光波長。作為增感劑,可含有公知者。可舉例如:雙(二甲基胺基)二苯甲酮、雙(二乙基胺基)二苯甲酮、二乙基9-氧硫
、N-苯基二乙醇胺、N-苯基甘胺酸、7-二乙基胺基-3-苯甲醯基香豆素、7-二乙基胺基-4-甲基香豆素、N-苯基
啉及該等之衍生物等,但並不限定於該等。
較佳為本發明之感光性樹脂組成物進而含有(D)交聯劑(以下,有時簡稱為「(D)成分」)。(D)成分係具有藉由熱進行交聯之官能基之化合物,作為具體之官能基,可舉例如:環氧基、氧雜環丁烷基及羥甲基等。
(D)成分較佳為含有自環氧化合物、氧雜環丁烷化合物及羥甲基化合物所構成之群組選擇之一種以上,從降低介電係數及介電損耗因數之觀點而言,更佳為含有羥甲基化合物。
作為環氧化合物,可含有公知者。可舉例如:Epolight(註冊商標)40E、Epolight 100E、Epolight 200E、Epolight 400E、Epolight 70P、Epolight 200P、Epolight 400P、Epolight 1500NP、Epolight 80MF、Epolight 4000、Epolight 3002(以上為商品名、共榮社化學股份有限公司製造)、DENACOL EX-212L、DENACOL EX-214L、DENACOL EX-216L、DENACOL EX-321L、DENACOL EX-850L(以上為商品名、長瀨化成股份有限公司製造)、Epikote828、Epikote1002、Epikote1750、Epikote1007、YX8100-BH30、E1256、E4250、E4275(以上為商品名、Japan Epoxy Resins股份有限公司製造)、Epiclon EXA-9583、Epiclon N695、HP4032、HP7200(以上為商品名、大日本油墨化學工業股份有限公司製造)、VG3101(商品名、三井化學股份有限公司製造)、TEPIC S、TEPIC G、TEPIC P(以上為商品名、日產化學工業股份有限公司製造)、Epotohto YH-434L(商品名、東都化成股份有限公司製造)、GAN、GOT、EPPN502H、NC3000或NC6000(以上為商品名、日本化藥股份有限公司製造)等。
作為氧雜環丁烷化合物,可含有公知者。可舉例如:OXT-101、OXT-121、OXT-212、OXT-221(以上為商品名、東亞合成股份有限公司製造)、ETERNACOLL EHO、ETERNACOLL OXBP、ETERNACOLL OXTP、ETERNACOLL OXMA、ETERNACOLL OXIPA(以上為商品名、宇部興產股份有限公司製造)或氧雜環丁烷化苯酚酚醛清漆等。
作為羥甲基化合物,可含有公知者。可舉例如:DML-PC、DML-PEP、DML-OC、DML-OEP、DML-34X、DML-PTBP、DML-PCHP、DML-OCHP、DML-PFP、DML-PSBP、DML-POP、DML-MBOC、DML-MBPC、DML-MTrisPC、DML-BisOC-Z、DML-BisOCHP-Z、DML-BPC、DML-BisOC-P、DMOM-PC、DMOM-PTBP、DMOM-MBPC、TriML-P、TriML-35XL、TML-HQ、TML-BP、TML-pp-BPF、TML-BPE、TML-BPA、TML-BPAF、TML-BPAP、TMOM-BP、TMOM-BPE、TMOM-BPA、TMOM-BPAF、TMOM-BPAP、HML-TPPHBA、HML-TPHAP、HMOM-TPPHBA、HMOM-TPHAP(以上為商品名、本州化學工業股份有限公司製造)、NIKALAC(註冊商標) MX-290、NIKALAC MX-280、NIKALAC MX-270、NIKALAC MX-279、NIKALAC MW-100LM、NIKALAC MX-750LM(以上為商品名、三和化學股份有限公司製造)。
於將(A)成分之總量設為100質量份之情形時,從獲得硬化膜之較高之耐化學品性方面、及降低介電係數及介電損耗因數之觀點而言,(D)成分之含量較佳為5質量份以上且100質量份以下,更佳為10質量份以上且90質量份以下。
感光性樹脂組成物亦可含有溶劑。作為溶劑,可舉例如:N-甲基-2-吡咯啶酮、γ-丁內酯、γ-戊內酯、δ-戊內酯、N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、二甲基亞碸、1,3-二甲基-2-咪唑啶酮、N,N'-二甲基丙烯脲、N,N-二甲基異丁醯胺、甲氧基-N,N-二甲基丙醯胺等極性非質子性溶劑;四氫呋喃、二
烷、丙二醇單甲醚、丙二醇單乙醚等醚類;丙酮、甲基乙基酮、二異丁基酮等酮類;乙酸乙酯、乙酸丁酯、乙酸異丁酯、乙酸丙酯、丙二醇單甲醚乙酸酯、乙酸3-甲基-3-甲氧基丁酯等酯類;乳酸乙酯、乳酸甲酯、二丙酮醇、3-甲基-3-甲氧基丁醇等醇類;甲苯、二甲苯等芳香族烴類等。以可含有該等之2種以上。
關於溶劑之含量,相對於(A)成分100質量份,為了使組成物溶解,較佳為含有100質量份以上,為了形成膜厚1 μm以上之塗佈膜,較佳為含有1,500質量份以下。
感光性樹脂組成物亦可含有公知之抗氧化劑、界面活性劑、密接性提昇劑。
本發明之硬化膜係使本發明之感光性樹脂組成物硬化而成者。
硬化膜可藉由如下方法獲得:將感光性樹脂組成物塗佈於基材,為了使溶劑揮發而進行乾燥。其後,視需要實施曝光及曝光後烘烤步驟後,施加150℃~350℃之溫度使之硬化。該加熱處理係選擇某溫度並階段性地升溫,或者選擇某溫度範圍並連續地升溫,並且實施5分鐘~5小時。作為一例,於130℃、200℃下進行各30分鐘熱處理。作為本發明中之固化條件之下限,較佳為170℃以上,但為了充分地進行硬化,更佳為180℃以上。又,固化條件之上限並無特別限制,從抑制膜收縮或應力之觀點而言,較佳為280℃以下,更佳為250℃以下,進而較佳為230℃以下。
於對硬化膜進行圖案加工之情形時,只要藉由具有塗佈樹脂組成物之步驟、乾燥步驟、曝光步驟、顯影步驟、曝光後烘烤步驟、加熱硬化之步驟等之公知之方法進行圖案加工即可。
本發明之電子零件具有本發明之硬化膜。
藉由本發明之感光性樹脂組成物形成之硬化膜可用作構成電子零件之絕緣膜、保護膜。
此處,作為電子零件,可舉例如:電晶體、二極體、積體電路(IC)、記憶體等具有半導體之主動零件;電阻、電容器、電感器等被動零件。又,亦將使用有半導體之電子零件稱為半導體裝置或半導體封裝。
作為電子零件內之硬化膜之具體例,可適宜地用於半導體之鈍化膜、半導體元件、薄膜電晶體(TFT,Thin Film Transistor)等之表面保護膜、2~10層之高密度安裝用多層配線中之再配線間之層間絕緣膜等層間絕緣膜、觸控面板顯示器之絕緣膜、保護膜、有機電致發光元件之絕緣層等用途,但並不限定於此,可採用各種構造。
又,形成硬化膜之基板表面可根據用途、步驟來適當選擇,可舉例如:矽、陶瓷、玻璃、金屬、環氧樹脂等,該等亦可於同一面內配置數種。
對使用有本發明之硬化膜之天線元件進行說明。本發明之天線元件係至少具備1種以上之天線配線、及本發明之硬化膜者,且該天線配線包含自彎折狀環形天線、線圈狀環形天線、彎折狀單極天線、彎折狀偶極天線或平面天線所構成之群組選擇之任一種以上,該天線配線中之每一個天線部之佔有面積為1000 mm
2以下,該硬化膜為使接地配線與天線配線間絕緣之絕緣膜。
圖1為屬於平面天線之一種之共面供電型微波傳輸帶天線之概略圖。1a表示剖面圖,1b表示俯視圖。首先,對形成方法進行說明。藉由在銅箔上塗佈本發明之感光性樹脂組成物並進行預烘烤,曝光後對銅箔進行層壓,使之熱硬化,形成於雙面具備銅箔之硬化膜。其後經過利用減成法之圖案化,可獲得具備圖1所示之微波傳輸帶線路(MSL)之銅配線之天線圖案的天線元件。
其次,對圖1之天線圖案進行說明。於1a中,15表示接地配線(整個面),16表示成為天線之基板之絕緣膜。其上層之11~13表示藉由上述圖案化所獲得之天線配線之剖面。接地配線厚度J及天線配線厚度K可根據阻抗之設計採用任意厚度,通常為2~20 μm。於1b中,11表示天線部,12表示匹配電路,13表示MSL供電線路,14表示供電點。為了實現天線部11與供電線路13之阻抗之整合,匹配電路12之長度M具有1/4λr之長度(λr=(傳輸電波之波長)/(絕緣材料介電係數)1/2)。又,天線部11之寬度W及長度L係設計為1/2λr之長度。天線部長度L亦可根據阻抗之設計,設為1/2λr以下。由於本發明之硬化膜為低介電係數、低介電損耗因數,故可提供高效率、高增益之天線元件。又,因該等特性,使用本發明之絕緣膜之天線元件適合作為用於高頻之天線,藉由將天線部之面積(=L×W)設為1000 mm
2以下之尺寸,可形成小型天線元件。以上述方式可獲得高效率、高增益、小型之用於高頻之天線元件。
其次,對具備IC晶片等半導體元件、再配線層、密封樹脂及天線配線之半導體封裝進行說明。本發明之半導體封裝係至少具備半導體元件、再配線層、密封樹脂及天線配線者,且該天線配線包含自彎折狀環形天線、線圈狀環形天線、彎折狀單極天線、彎折狀偶極天線及微波傳輸帶天線所構成之群組選擇之至少一種以上,該天線配線中之每一個天線部之佔有面積為1000 mm
2以下,該再配線層之絕緣層、及/或該密封樹脂包含本發明之硬化膜,該密封樹脂位於接地配線與天線配線間。
圖2為與具備IC晶片(半導體元件)、再配線、密封樹脂及天線元件之半導體封裝之剖面相關之概略圖。於IC晶片201之電極墊202上,由銅配線209、及利用本發明之硬化膜形成之絕緣膜210形成再配線層(銅2層、絕緣膜3層)。於再配線層(銅配線209及絕緣膜210)之焊墊上形成障壁金屬211與焊料凸塊212。為了將上述IC晶片密封,利用本發明之硬化膜形成第1密封樹脂208,進而於其上形成作為天線用之接地配線之銅配線209。經由形成於第1密封樹脂208內之導孔,形成連接接地配線206與再配線層(銅配線209及絕緣膜210)之第1通孔配線207。於第1密封樹脂208及接地配線206上,利用本發明之硬化膜形成第2密封樹脂205,並於其上形成平面天線配線204。經由形成於第1密封樹脂208及第2密封樹脂205內之導孔,形成連接平面天線配線204與再配線層(銅配線209及絕緣膜210)之第2通孔配線203。作為絕緣膜210之每一層之厚度,較佳為10~20 μm,作為第1密封樹脂及第2密封樹脂,分別較佳為50~200 μm及100~400 μm。由於本發明之硬化膜為低介電係數、低介電損耗因數,故具備所獲得之天線元件之半導體封裝為高效率、高增益,且封裝內之傳輸損耗較小。
即,較佳為本發明之電子零件係至少包含1種以上之天線配線、及具備本發明之硬化膜之天線元件者,且該天線配線包含自彎折狀環形天線、線圈狀環形天線、彎折狀單極天線、彎折狀偶極天線或平面天線所構成之群組選擇之任一種以上,該天線配線中之每一個天線部之佔有面積為1000 mm
2以下,該硬化膜為使接地配線與天線配線間絕緣之絕緣膜。
進而較佳為,本發明之電子零件係包含至少具備半導體元件、再配線層、密封樹脂、天線配線之半導體封裝者,且該再配線層之絕緣層及/或該密封樹脂包含本發明之硬化膜,該密封樹脂亦兼具作為使接地配線與天線配線間絕緣之絕緣膜之功能。
進而較佳為,本發明之電子零件係具備積層天線配線及本發明之硬化膜而獲得之天線元件者,且天線配線之高度為50~200 μm,該硬化膜之厚度為80~300 μm。藉由積層天線配線及硬化膜,將天線配線之高度及硬化膜之厚度設為上述範圍內,小型且能夠於廣範圍內收發,且由於本發明之硬化膜為低介電係數、低介電損耗因數,故可提供高效率、高增益之天線元件。
又,本發明之化合物為式(1)所表示之化合物或式(2)所表示之化合物。
式(1)中,W
1及W
2分別獨立地表示式(3)或式(4)所表示之基。式(1)中,a、b、c及d分別獨立地為滿足a+b=6~17、c+d=8~19之自然數,虛線部意指碳-碳單鍵或碳-碳雙鍵。
式(2)中,W
3及W
4分別獨立地表示式(3)或式(4)所表示之基。式(2)中,e、f、g及h分別獨立地為滿足e+f=5~16、g+h=8~19之自然數,虛線部意指碳-碳單鍵或碳-碳雙鍵。
式(3)及式(4)中,X及Y表示-NH-。R
1表示單鍵或包含碳數1~5之二~六價有機基。R
2表示單鍵或包含碳數1~5之二價有機基。i表示1~5之整數。*表示鍵結點。
本發明之化合物由於能夠利用自由基聚合進行交聯,故藉由與光或熱自由基產生劑組合,能夠容易地硬化,且其硬化膜為低介電係數、低介電損耗因數。又,於有機溶劑中之溶解性較高,與多數樹脂之相溶性優異。因此,可對各種樹脂賦予低介電特性。獲得該等特性之原因並不確定,但推測其原因在於分子內同時具有低極性部位與高極性部位。
[實施例]
以下,列舉實施例來說明本發明,但本發明並不受該等例之限定。首先,對各實施例及比較例中之評價方法進行說明。評價係使用預先以平均孔徑1 μm之聚四氟乙烯製之過濾器(住友電氣工業股份有限公司製造)過濾後之硬化前的感光性樹脂組成物(以下稱為清漆)。
(1)圖案加工性
使用旋轉塗佈機(Mikasa股份有限公司製造之1H-360S)將清漆旋轉塗佈於矽晶圓後,使用加熱板(大日本網屏製造股份有限公司製造之SCW-636)於100℃下進行3分鐘預烘烤,製作膜厚11 μm之預烘烤膜。對所獲得之預烘烤膜,使用平行光光罩對準曝光機(以下稱為PLA)(佳能股份有限公司製造之PLA-501F),將超高壓水銀燈作為光源(混合g、h、i射線),介隔30 μm之具有1:1之線與間隙圖案的光罩,藉由接觸進行500 mJ/cm
2曝光。
其後,於120℃下進行1分鐘曝光後烘烤,使用塗佈顯影裝置MARK-7進行顯影。於利用有機溶劑進行顯影之情形時,對所評價之材料使用適當之顯影液進行槳式顯影,繼而同樣地以適當之沖洗液沖洗。所使用之顯影液及沖洗液係示於表4。又,於感光性樹脂組成物溶解於鹼性水溶液之情形時,以2.38質量%之四甲基銨(TMAH)水溶液進行顯影,繼而以純水沖洗。
關於顯影時間,預先對各預烘烤膜,將顯影開始之時間設為0秒,於0秒~90秒之期間測量預烘烤膜於顯影液中全部溶出之時間,於在0秒~90秒之期間預烘烤膜全部溶出之情形時,將其2倍之時間設為顯影時間。另一方面,於自顯影開始90秒以內預烘烤膜未全部溶出之情形時,將顯影時間設為3分鐘來實施。沖洗時間均設為30秒鐘。顯影後觀察圖案加工部,將殘渣未殘留於30 μm之1:1之線與間隙中之間隙部者評價為A,將可見殘渣者評價為B,將膜未溶解於顯影液而殘留者評價為C,對顯影性進行評價。
顯影後測定膜厚,並測定殘膜率,殘膜率係將預烘烤膜厚設為100時之曝光部之顯影後膜厚除以預烘烤膜厚所得。將殘膜率為80%以上者評價為感度A,將50%以上且未滿80%評價為感度B,將未滿50%評價為感度C,對感度進行評價。再者,膜厚係使用大日本網屏製造股份有限公司製造之Lambda ACE STM-602,以折射率1.629進行測定。以下所記載之膜厚亦同樣。
(2)介電係數、介電損耗因數之測定
以於120℃下3分鐘之預烘烤後之膜厚成為11 μm之方式,使用塗佈顯影裝置Mark-7,藉由旋轉塗佈法將清漆塗佈於6英吋之矽晶圓上及進行預烘烤,其後使用PLA於整個面進行300 mJ/cm
2曝光,使用無氧化烘箱CLH-21CD-S(Koyo Thermo Systems股份有限公司製造),於氧濃度20 ppm以下以3.5℃/min升溫至220℃,於各溫度下進行1小時加熱處理。於溫度達到50℃以下時取出矽晶圓,於45質量%之氫氟酸中浸漬5分鐘,藉此自晶圓剝離樹脂組成物之硬化膜。將該膜切斷為寬度3 cm、長度10 cm之短條狀,於室溫23.0℃、濕度45.0%RH下,藉由依據美國材料試驗協會(ASTM,American Society for Testing Materials)D2520之擾動方式空腔共振器法測定頻率1 GHz下之介電係數及介電損耗因數。如以下之表1所示,以5等級判定介電特性。
[表1]
[表1] | |||
介電特性評價(1 GHz) | 未滿3.0 | 3.0以上且未滿3.5 | 3.5以上 |
介電係數 介電損耗因數 | |||
未滿0.010 | A | B | C |
0.010以上且未滿0.015 | B | C | D |
0.015以上 | C | D | E |
(3)玻璃轉移點之測定
以與上述「(2)介電係數、介電損耗因數之測定」同樣之方式製作硬化膜之獨立膜,以成為3.0 cm×1.5 cm之方式利用單刃切割藉由該方法獲得之硬化膜,使用熱機械分析裝置(精工電子股份有限公司製造、TMA/SS6100),於氮氣氣流下80 mL/min之條件下,以10℃/min之速度自25℃升溫至400℃,並進行測定(測定方法(I))。又,關於所獲得之硬化膜無法以獨立膜之形式獲得者,係對該硬化膜(a)進行削取,使用示差掃描熱量計(島津製作所製造、DSC-50),於氮氣環境下,以10℃/min之速度自25℃升溫至400℃,並進行測定(測定方法(II))。評價基準如下所述,以4等級進行評價。玻璃轉移點較高者表示硬化膜之耐熱性較高。
A:玻璃轉移點之值為200℃以上
B:玻璃轉移點之值為170℃以上且未滿200℃
C:玻璃轉移點之值為140℃以上且未滿170℃
D:玻璃轉移點之值未滿140℃。
(4)固化後之硬化膜之斷裂點伸長率之測定
以與上述「(2)介電係數、介電損耗因數之測定」同樣之方式製作硬化膜之獨立膜,將該膜切斷為寬度1.5 cm、長度9 cm之短條狀,使用Tensilon RTM-100(Orientec股份有限公司製造),於室溫23.0℃、濕度45.0%RH下以拉伸速度50 mm/min拉伸(夾頭間隔=2 cm),進行斷裂點伸長率(%)之測定。測定係每1檢體對10片短條進行,根據結果求出數值較高之排名前5片之平均值。
以下,記載合成例、實施例中所使用之化合物之簡稱。
Priamine1075:二聚二胺化合物(商品名、Croda Japan股份有限公司製造)(平均胺值:205)
Karenz AOI:異氰酸2-丙烯醯氧基乙酯(商品名、昭和電工股份有限公司製造)
Karenz BEI:異氰酸1,1-(雙丙烯醯氧基甲基)乙酯(商品名、昭和電工股份有限公司製造)
Polyflow77:丙烯酸系界面活性劑(商品名、共榮社化學股份有限公司製造)
矽酸甲酯51:矽酸酯低聚物(商品名、COLCOAT股份有限公司製造)
SiDA:1,3-雙(3-胺基丙基)四甲基二矽氧烷
BAHF:2,2-雙(3-胺基-4-羥基苯基)六氟丙烷
BFE:1,2-雙(4-甲醯基苯基)乙烷
CP:環戊酮
CYCLOTENE4026-46:苯并環丁烯溶液(商品名、陶氏化學股份有限公司製造)
DCP-A:二環戊二烯二甲基丙烯酸酯(商品名、共榮社化學股份有限公司製造)
DFA:二甲基甲醯胺二甲基縮醛
EL:乳酸乙酯
HEMA:甲基丙烯酸2-羥基乙酯
HA:2,2-雙[3-(3-胺基苯甲醯胺)-4-羥基苯基]六氟丙烷
H
2O:超純水
IPA:2-丙醇
IRGANOX3114:受阻酚系抗氧化劑(商品名、BASF股份有限公司製造)
GBL:γ-丁內酯
KC Cleaner NX:C10-12之異烷烴(商品名、京葉化學股份有限公司製造)
MEHC-7851SS:酚樹脂(商品名、明和化成股份有限公司製造)
MOM:4-[1,1-雙[4-羥基-3,5-雙(甲氧基甲基)苯基]乙基]-2,6-雙(甲氧基甲基)苯酚
NA:5-降
烯-2,3-二羧酸酐
NCI-831:光聚合起始劑(商品名、ADEKA股份有限公司製造)
NMP:N-甲基-2-吡咯啶酮
ODPA:3,3',4,4'-二苯醚四羧酸二酐
OXT-121:氧雜環丁烷化合物(商品名、東亞合成股份有限公司製造)
PGMEA:丙二醇甲醚乙酸酯
TMAH:四甲基銨水溶液
VG-3101:單體型三苯甲烷型環氧樹脂(商品名、Printec股份有限公司製造)
U-847:具有胺基甲酸酯基之下述構造之丙烯酸系單體(商品名、Designer Molcules Inc.製造)
XIRAN2000:苯乙烯順丁烯二酸酐共聚合體樹脂(商品名、巴工業股份有限公司製造)
APL6015T:環烯烴聚合物(商品名、三井化學股份有限公司製造)
BMI-689:具有順丁烯二醯亞胺基之下述構造之單體(商品名、Designer Molcules Inc.製造)
[實施例1 多官能單體(M-1)之合成]
於乾燥氮氣氣流下,於三口燒瓶中,投入Karenz AOI 28.22 g(0.20 mol)及甲苯28.22 g並攪拌。進而滴加於甲苯53.50 g中溶解有Priamine1075 53.50 g(0.10 mol)之溶液。滴加結束後,於室溫下攪拌12小時後,利用蒸發器去除甲苯,獲得多官能單體(M-1)。所獲得之多官能單體之構造之鑑定使用核磁共振裝置(日本電子股份有限公司製造、JNM-ECZ400R)。將結果示於以下。
1H-NMR (DMSO): 6.4 (d, 2H), 6.0 - 6.2 (m, 6H), 5.8 (d, 2H), 4.3 (m, 4H), 3.4 (m, 4H), 3.1 (m, 4H), 1.2 - 1.5 (m, 60H), 0.9 (t, 6H)。
[實施例2 多官能單體(M-2)之合成]
除了將合成例1之Karenz AOI 28.22 g(0.20 mol)變更為Karenz BEI 47.84 g(0.20莫耳)以外,與合成例1同樣地實施,獲得多官能單體(M-2)。將用於所獲得之多官能單體之構造鑑定的NMR之結果示於以下。
1H-NMR (DMSO): 6.4 - 6.6 (m, 6H), 6.0 - 6.2 (m, 6H), 5.8 (d, 4H), 4.8 (s, 8H), 3.1 (m, 4H), 1.6 (s, 6H), 1.2 - 1.5 (m, 60H), 0.9 (t, 6H)。
[合成例1 聚醯亞胺(P-1)之合成]
於乾燥氮氣氣流下,秤量BAHF 31.13 g(0.085 mol)、SiDA 1.24 g(0.0050 mol)、作為末端終止劑之MAP 2.18 g(0.020 mol)、NMP 150.00 g置於三口燒瓶中,使其溶解。向其中添加於NMP 50.00 g中溶解有ODPA 31.02 g(0.10 mol;相對於源自全部羧酸及其衍生物之構造單位為100 mol%)之溶液,於20℃下攪拌1小時,繼而於50℃下攪拌4小時。其後,添加二甲苯15 g,一面使水與二甲苯一起共沸,一面於150℃下攪拌5小時。反應結束後,將反應溶液投入至水3 L中,過濾獲得析出之固體沈澱。將所獲得之固體以水洗淨3次後,利用80℃之真空乾燥機乾燥24小時,獲得聚醯亞胺(P-1)。
[合成例2 聚醯胺(P-2)之合成]
秤量雙(4-胺基環己基)甲烷19.98 g(0.095 mol;相對於源自全部胺及其衍生物之構造單位為95.0 mol%)、SiDA 1.24 g(0.0050 mol;相對於源自全部胺及其衍生物之構造單位為5.0 mol%)、NMP 70.00 g置於安裝有充滿甲苯之迪安-斯塔克水分離器及冷凝管之500 mL圓底燒瓶中,使其溶解。向其中添加於NMP 20.00 g中溶解有BFE 19.06 g(0.080 mol;相對於源自全部羧酸及其衍生物之構造單位為66.7 mol%)之溶液,於20℃下攪拌1小時,繼而於50℃下攪拌2小時。其次,添加作為末端終止劑之NMP 10 g中溶解有NA 6.57 g(0.040 mol;相對於源自全部羧酸及其衍生物之構造單位為33.3 mol%)之溶液,於50℃下攪拌2小時。其後,於氮氣環境下,於100℃下攪拌2小時。反應結束後,將反應溶液投入至水3 L中,過濾獲得析出之固體沈澱。將所獲得之固體以水洗淨3次後,利用80℃之真空乾燥機乾燥24小時,獲得聚醯胺(P-2)。
[合成例3 聚脲(P-3)之合成]
於乾燥氮氣氣流下,於三口燒瓶中,投入使4,4'-二苯甲烷二異氰酸酯6.00 g(0.020 mol)溶解於NMP 30 g中而成之溶液。一面攪拌燒瓶內之溶液,一面向該溶液中添加使甲基丙烯酸2-(3',5'-二胺基苄氧基)乙酯3.52 g(0.013 mol)溶解於NMP 20 g中而成之溶液,於50℃下攪拌4小時。反應結束後,將反應溶液投入至甲醇500 g中,過濾獲得析出之固體沈澱。利用真空乾燥器將所獲得之固體乾燥24小時,獲得聚脲(P-3)。
[合成例4 聚酯樹脂溶液(P-4)之合成]
添加148 g之1,1-雙(4-(2,3-環氧丙氧基)苯基)-3-苯基茚烷、47 g之丙烯酸、1 g之乙酸四丁基銨(以下稱為TBAA)、2.0 g之第三丁基兒茶酚及244 g之PGMEA,於120℃下攪拌5小時。冷卻至室溫後,添加30 g之聯苯四羧酸二酐及1 g之TBAA並於110℃下攪拌3小時。冷卻至室溫後,添加15 g之四氫鄰苯二甲酸酐並於120℃下攪拌5小時。反應結束後,添加500 g之PGMEA,為了去除加成觸媒,利用1當量濃度之甲酸水溶液對反應溶液進行分液萃取處理,利用硫酸鎂乾燥後,以固形份濃度成為40 wt%之方式利用旋轉蒸發器進行濃縮,獲得聚酯樹脂溶液(P-4)。
[合成例5 聚矽氧烷溶液(P-5)之合成]
於乾燥氮氣氣流下,於500 ml之三口燒瓶中添加甲基三甲氧基矽烷54.48 g(0.40 mol)、苯基三甲氧基矽烷99.15 g(0.50 mol)、2-(3,4-環氧環己基)乙基三甲氧基矽烷12.32 g(0.05 mol)、矽酸甲酯51 5.88 g(相當於Si原子莫耳數0.05莫耳)、丙二醇單甲醚乙酸酯(以下有時亦記載為PGMEA)155.04 g,於室溫下一面攪拌,一面歷時10分鐘添加於水54.45 g中溶解有磷酸0.515 g(相對於添加單體為0.30質量份)之磷酸水溶液。其後,將燒瓶浸漬於40℃之油浴中,攪拌60分鐘後,歷時30分鐘將油浴升溫至115℃。升溫開始1小時後,溶液之內溫達到100℃,自此時起加熱攪拌2小時(內溫為100℃),獲得聚矽氧烷溶液(P-5)。
[合成例6丙烯酸系樹脂溶液(P-6)之合成]
於500 ml之燒瓶中添加2,2'-偶氮雙(異丁腈)3 g、PGMEA 50 g。其後,添加甲基丙烯酸23.0 g、甲基丙烯酸苄酯31.5 g、甲基丙烯酸三環[5.2.1.02,6]癸烷-8-基酯32.8 g,於室溫下攪拌片刻,藉由吹泡通入氮氣對燒瓶內充分地進行氮氣置換後,於70℃下加熱攪拌5小時。其次,於所獲得之溶液中添加甲基丙烯酸縮水甘油酯12.7 g、二甲基苄基胺1 g、對甲氧基苯酚0.2 g、PGMEA 100 g,於90℃下加熱攪拌4小時。攪拌後,以固形份濃度成為40 wt%之方式添加PGMEA,獲得丙烯酸系樹脂溶液(P-6)。
[合成例7 聚醯亞胺前驅物(P-7)之合成]
於乾燥氮氣氣流下,於三口燒瓶中,將ODPA 31.02 g(0.10 mol)加入至500 ml容量之可分離式燒瓶中,並加入HEMA 26.03 g(0.20 mol)與NMP 123.0 ml,於室溫下一面攪拌一面添加三乙基胺22.26 g(0.22 mol),獲得反應混合物。於由反應引起之放熱結束後,放置冷卻至室溫,再放置16小時。其次,將溫度升溫至40℃,將(2,3-二氫-2-側硫基-3-苯并
唑基)膦酸二苯酯76.7 g(0.2 mol)添加至反應混合物中,攪拌30分鐘。進而於室溫下攪拌2小時後,添加雙(4-胺基環己基)甲烷17.88 g(0.085 mol;相對於源自全部胺及其衍生物之構造單位為77.3 mol%)、SiDA 1.24 g(0.0050 mol;相對於源自全部胺及其衍生物之構造單位為4.5 mol%)、作為末端終止劑之MAP 2.18 g(0.020 mol;相對於源自全部胺及其衍生物之構造單位為18.2 mol%)、NMP 77.00 g並攪拌1小時,獲得反應液。將所獲得之反應液放置冷卻至室溫,添加至3 L之水中,生成包含粗聚合物之沈澱物。藉由過濾收集該沈澱,以水洗淨3次後,以異丙醇500 mL洗淨2次,並進行真空乾燥,獲得粉末狀之聚醯亞胺前驅物(P-7)。
[合成例8 聚醯亞胺前驅物(P-8)之合成]
除了將HEMA 26.03 g(0.20 mol)變更為油醇53.70 g(0.20 mol)以外,與合成例5同樣地實施,獲得聚醯亞胺前驅物(P-8)。
[合成例9 聚醯亞胺前驅物(P-9)之合成]
於乾燥氮氣氣流下,使HA 51.4 g(0.085莫耳)、SiDA 1.24 g(0.005莫耳)、作為末端終止劑之MAP 2.18 g(0.020 mol)溶解於NMP 200 g中。向其中添加ODPA 31.0 g(0.10莫耳),於40℃下攪拌2小時。其後,歷時10分鐘滴加以NMP 5 g稀釋DFA 7.14 g(0.06莫耳)所得之溶液。滴加後,於40℃下持續攪拌2小時。攪拌結束後,將溶液投入至水2 L中,藉由過濾收集聚合物固體之沈澱。進而以水2 L進行3次洗淨,利用50℃之真空乾燥機將所收集之聚合物固體乾燥72小時,獲得聚醯亞胺前驅物(P-9)。
[合成例10聚苯并
唑(P-10)之合成]
秤量BAHF 34.79 g(0.095 mol;相對於源自全部胺及其衍生物之構造單位為95.0 mol%)、SiDA 1.24 g(0.0050 mol;相對於源自全部胺及其衍生物之構造單位為5.0 mol%)、NMP 75.00 g置於安裝有充滿甲苯之迪安-斯塔克水分離器及冷凝管之500 mL圓底燒瓶中,並使該等溶解。向其中添加於NMP 25.00 g中溶解有BFE 19.06 g(0.080 mol;相對於源自全部羧酸及其衍生物之構造單位為66.7 mol%)、作為末端終止劑之NA 6.57 g(0.040 mol;相對於源自全部羧酸及其衍生物之構造單位為33.3 mol%)之溶液,於20℃下攪拌1小時,繼而於50℃下攪拌1小時。其後,於氮氣環境下,於200℃以上加熱攪拌10小時,進行脫水反應。反應結束後,將反應溶液投入至水3 L中,過濾獲得析出之固體沈澱。將所獲得之固體以水洗淨3次後,利用80℃之真空乾燥機乾燥24小時,獲得聚苯并
唑(P-10)。
[合成例11 聚苯并
唑前驅物(P-11)之合成]
秤量BAHF 34.79 g(0.095 mol;相對於源自全部胺及其衍生物之構造單位為95.0 mol%)、SiDA 1.24 g(0.0050 mol;相對於源自全部胺及其衍生物之構造單位為5.0 mol%)、NMP 70.00 g置於安裝有充滿甲苯之迪安-斯塔克水分離器及冷凝管之500 mL圓底燒瓶中,並使該等溶解。向其中添加於NMP 20.00 g中溶解有BFE 19.06 g(0.080 mol;相對於源自全部羧酸及其衍生物之構造單位為66.7 mol%)之溶液,於20℃下攪拌1小時,繼而於50℃下攪拌2小時。其次,添加作為末端終止劑之NMP 10 g中溶解有NA 6.57 g(0.040 mol;相對於源自全部羧酸及其衍生物之構造單位為33.3 mol%)之溶液,於50℃下攪拌2小時。其後,於氮氣環境下,於100℃下攪拌2小時。反應結束後,將反應溶液投入至水3 L中,過濾獲得析出之固體沈澱。將所獲得之固體以水洗淨3次後,利用80℃之真空乾燥機乾燥24小時,獲得聚苯并
唑前驅物(P-11)。
[合成例12 聚醯亞胺(P-12)之合成]
於乾燥氮氣氣流下,秤量BAHF 27.47 g(0.075 mol)、SiDA 1.24 g(0.0050 mol)、Priamine1075 5.35 g(0.010 mol)、作為末端終止劑之MAP 2.18 g(0.020 mol)、NMP 150.00 g置於三口燒瓶中,並使該等溶解。向其中添加於NMP 50.00 g中溶解有ODPA 31.02 g(0.10 mol)之溶液,於20℃下攪拌1小時,繼而於50℃下攪拌4小時。其後,添加二甲苯15 g,一面使水與二甲苯一起共沸,一面於150℃下攪拌5小時。反應結束後,將反應溶液投入至水3 L中,過濾獲得析出之固體沈澱。將所獲得之固體以水洗淨3次後,利用80℃之真空乾燥機乾燥24小時,獲得聚醯亞胺(P-12)。
[實施例3]
於黃色燈下,使BMI-689 10.00 g、聚醯亞胺樹脂(P-1)10.00 g、NCI-831 0.50 g、IRGANOX3114 0.10 g、3-三甲氧基矽烷基鄰苯二甲醯胺酸0.30 g溶解於NMP 20.00 g中,添加Polyflow77之1質量%EL溶液0.10 g,進行攪拌而獲得清漆。對所獲得之清漆之特性,藉由上述評價方法,測定圖案加工性、介電係數、介電損耗因數、玻璃轉移點及斷裂點伸長率。
[實施例4]
除了將BMI-689變更為U-847以外,與實施例3同樣地實施。
[實施例5]
於黃色燈下,使M-1 10.00 g、聚醯胺樹脂(P-2)10.00 g、NCI-831 0.50 g、IRGANOX3114 0.10 g、3-三甲氧基矽烷基鄰苯二甲醯胺酸0.30 g溶解於NMP 20.00 g中,添加Polyflow77之1質量%EL溶液0.10 g,進行攪拌而獲得清漆。所獲得之清漆之特性係實施與實施例3同樣之測定。
[實施例6]
除了將P-2變更為P-3以外,與實施例5同樣地實施。
[實施例7]
除了將P-2變更為P-4以外,與實施例5同樣地實施。
[實施例8]
除了將P-2變更為P-5以外,與實施例5同樣地實施。
[實施例9]
除了將P-2變更為P-6以外,與實施例5同樣地實施。
[實施例10]
除了將P-2變更為MEHC-7851SS以外,與實施例5同樣地實施。
[實施例11]
除了將P-2變更為CYCLOTENE4026-46以外,與實施例5同樣地實施。
[實施例12]
於黃色燈下,使M-1 10.00 g、XIRAN2000 10.00 g、NCI-831 0.50 g、IRGANOX3114 0.10 g、3-三甲氧基矽烷基鄰苯二甲醯胺酸0.30 g溶解於甲苯20.00 g中,添加Polyflow77之1質量%EL溶液0.10 g,進行攪拌而獲得清漆。所獲得之清漆之特性係實施與實施例3同樣之測定。
[實施例13]
除了將XIRAN2000變更為APL6015T以外,與實施例12同樣地實施。
[實施例14]
除了將P-2變更為P-1以外,與實施例5同樣地實施。
[實施例15]
除了將M-1變更為M-2以外,與實施例14同樣地實施。
[實施例16]
除了將P-2變更為P-7以外,與實施例5同樣地實施。
[實施例17]
除了將P-2變更為P-8以外,與實施例5同樣地實施。
[實施例18]
除了將P-2變更為P-9以外,與實施例5同樣地實施。
[實施例19]
除了將P-2變更為P-10以外,與實施例5同樣地實施。
[實施例20]
除了將P-2變更為P-11以外,與實施例5同樣地實施。
[實施例21]
除了將P-2變更為P-12以外,與實施例5同樣地實施。
[實施例22]
除了將P-2 10.00 g變更為P-12 8.00 g與MEHC-7851SS 2.00 g以外,與實施例5同樣地實施。
[實施例23]
於實施例22中添加VG-3101 2.00 g,並與實施例22同樣地實施。
[實施例24]
於實施例22中添加OXT-121 2.00g,並與實施例22同樣地實施。
[實施例25]
於實施例22中添加MOM 2.00 g,並與實施例22同樣地實施。
[比較例1]
於黃色燈下,使P-1 10.00 g、DCP-A 10.00 g、NCI-831 0.50 g、IRGANOX3114 0.10g、3-三甲氧基矽烷基鄰苯二甲醯胺酸0.30 g、MOM 2.00 g溶解於NMP 27.00 g中,添加Polyflow77之1質量%EL溶液0.10 g,進行攪拌而獲得清漆。對所獲得之清漆之特性,藉由上述評價方法,測定圖案加工性、介電係數、介電損耗因數、玻璃轉移點及斷裂點伸長率。
[表2]
[表2] | |||||
去除溶劑之清漆組成(質量份) | |||||
多官能單體(A) | 黏合劑樹脂(B) | 光聚合起始劑(C) | 交聯劑(D) | 其他成分 | |
實施例3 | BMI-689(100) | P-1(100) | NCI-831(5) | ‒ | IRGANOX3114(1) 3-三甲氧基矽烷基鄰苯二甲醯胺酸(3) Polyflow77(0.01) |
實施例4 | U-847(100) | P-1(100) | NCI-831(5) | ‒ | IRGANOX3114(1) 3-三甲氧基矽烷基鄰苯二甲醯胺酸(3) Polyflow77(0.01) |
實施例5 | M-1(100) | P-2(100) | NCI-831(5) | ‒ | IRGANOX3114(1) 3-三甲氧基矽烷基鄰苯二甲醯胺酸(3) Polyflow77(0.01) |
實施例6 | M-1(100) | P-3(100) | NCI-831(5) | ‒ | IRGANOX3114(1) 3-三甲氧基矽烷基鄰苯二甲醯胺酸(3) Polyflow77(0.01) |
實施例7 | M-1(100) | P-4(100) | NCI-831(5) | ‒ | IRGANOX3114(1) 3-三甲氧基矽烷基鄰苯二甲醯胺酸(3) Polyflow77(0.01) |
實施例8 | M-1(100) | P-5(100) | NCI-831(5) | ‒ | IRGANOX3114(1) 3-三甲氧基矽烷基鄰苯二甲醯胺酸(3) Polyflow77(0.01) |
實施例9 | M-1(100) | P-6(100) | NCI-831(5) | ‒ | IRGANOX3114(1) 3-三甲氧基矽烷基鄰苯二甲醯胺酸(3) Polyflow77(0.01) |
實施例10 | M-1(100) | MEHC-7851SS(100) | NCI-831(5) | ‒ | IRGANOX3114(1) 3-三甲氧基矽烷基鄰苯二甲醯胺酸(3) Polyflow77(0.01) |
實施例11 | M-1(100) | CYCLOTENE4026-46(100) | NCI-831(5) | ‒ | IRGANOX3114(1) 3-三甲氧基矽烷基鄰苯二甲醯胺酸(3) Polyflow77(0.01) |
實施例12 | M-1(100) | XIRAN2000(100) | NCI-831(5) | ‒ | IRGANOX3114(1) 3-三甲氧基矽烷基鄰苯二甲醯胺酸(3) Polyflow77(0.01) |
實施例13 | M-1(100) | APL6015T(100) | NCI-831(5) | ‒ | IRGANOX3114(1) 3-三甲氧基矽烷基鄰苯二甲醯胺酸(3) Polyflow77(0.01) |
實施例14 | M-1(100) | P-1(100) | NCI-831(5) | ‒ | IRGANOX3114(1) 3-三甲氧基矽烷基鄰苯二甲醯胺酸(3) Polyflow77(0.01) |
[表3]
[表3] | |||||
去除溶劑之清漆組成(質量份) | |||||
多官能單體(A) | 黏合劑樹脂(B) | 光聚合起始劑(C) | 交聯劑(D) | 其他成分 | |
實施例15 | M-2(100) | P-1(100) | NCI-831(5) | ‒ | IRGANOX3114(1) 3-三甲氧基矽烷基鄰苯二甲醯胺酸(3) Polyflow77(0.01) |
實施例16 | M-1(100) | P-7(100) | NCI-831(5) | ‒ | IRGANOX3114(1) 3-三甲氧基矽烷基鄰苯二甲醯胺酸(3) Polyflow77(0.01) |
實施例17 | M-1(100) | P-8(100) | NCI-831(5) | ‒ | IRGANOX3114(1) 3-三甲氧基矽烷基鄰苯二甲醯胺酸(3) Polyflow77(0.01) |
實施例18 | M-1(100) | P-9(100) | NCI-831(5) | ‒ | IRGANOX3114(1) 3-三甲氧基矽烷基鄰苯二甲醯胺酸(3) Polyflow77(0.01) |
實施例19 | M-1(100) | P-10(100) | NCI-831(5) | ‒ | IRGANOX3114(1) 3-三甲氧基矽烷基鄰苯二甲醯胺酸(3) Polyflow77(0.01) |
實施例20 | M-1(100) | P-11(100) | NCI-831(5) | ‒ | IRGANOX3114(1) 3-三甲氧基矽烷基鄰苯二甲醯胺酸(3) Polyflow77(0.01) |
實施例21 | M-1(100) | P-12(100) | NCI-831(5) | ‒ | IRGANOX3114(1) 3-三甲氧基矽烷基鄰苯二甲醯胺酸(3) Polyflow77(0.01) |
實施例22 | M-1(100) | P-11(80) MEHC-7851SS(20) | NCI-831(5) | ‒ | IRGANOX3114(1) 3-三甲氧基矽烷基鄰苯二甲醯胺酸(3) Polyflow77(0.01) |
實施例23 | M-1(100) | P-11(80) MEHC-7851SS(20) | NCI-831(5) | VG-3101(20) | IRGANOX3114(1) 3-三甲氧基矽烷基鄰苯二甲醯胺酸(3) Polyflow77(0.01) |
實施例24 | M-1(100) | P-11(80) MEHC-7851SS(20) | NCI-831(5) | OXT-121(20) | IRGANOX3114(1) 3-三甲氧基矽烷基鄰苯二甲醯胺酸(3) Polyflow77(0.01) |
實施例25 | M-1(100) | P-11(80) MEHC-7851SS(20) | NCI-831(5) | MOM(20) | IRGANOX3114(1) 3-三甲氧基矽烷基鄰苯二甲醯胺酸(3) Polyflow77(0.01) |
比較例1 | DCP-A(100) | P-1(100) | NCI-831(5) | MOM(20) | IRGANOX3114(1) 3-三甲氧基矽烷基鄰苯二甲醯胺酸(3) Polyflow77(0.01) |
[表4]
[表4] | |||||||||||
評價結果 | |||||||||||
顯影液 | 沖洗液 | 圖案加工性 | 介電特性(1 GHz) | 耐熱性 | 斷裂點伸長率 | ||||||
顯影性 | 感度 | 介電係數 | 介電損耗因數 | 判定 | 玻璃轉移點 (℃) | 判定 | 伸長率 (%) | 判定 | |||
實施例3 | CP | IPA | B | C | 2.7 | 0.005 | A | 140 | D | 40 | A |
實施例4 | TMAH | H 2O | A | A | 3.0 | 0.009 | B | 150 | C | 40 | A |
實施例5 | CP | IPA | A | A | 3.1 | 0.007 | B | 110 | D | 200 | A |
實施例6 | CP | IPA | A | A | 3.1 | 0.006 | B | 110 | D | 200 | A |
實施例7 | CP | IPA | A | A | 3.0 | 0.005 | B | 120 | D | 120 | A |
實施例8 | TMAH | H 2O | A | A | 2.7 | 0.005 | A | 120 | D | 5 | C |
實施例9 | TMAH | H 2O | A | A | 2.9 | 0.011 | B | 100 | D | 5 | C |
實施例10 | TMAH | H 2O | A | A | 2.9 | 0.004 | A | 110 | D | 5 | C |
實施例11 | 二丙二醇二甲醚30% KC Cleaner NX70% | IPA | A | A | 2.6 | 0.003 | A | 160 | C | 5 | C |
實施例12 | 甲苯 | IPA | A | A | 2.9 | 0.004 | A | 120 | D | 30 | A |
實施例13 | 甲苯 | IPA | A | A | 2.5 | 0.002 | A | 100 | D | 5 | C |
實施例14 | TMAH | H 2O | A | A | 2.8 | 0.005 | A | 160 | C | 40 | A |
實施例15 | TMAH | H 2O | A | A | 2.9 | 0.009 | A | 160 | C | 30 | A |
實施例16 | CP | IPA | A | A | 2.9 | 0.007 | A | 160 | C | 40 | A |
實施例17 | CP | IPA | A | A | 2.9 | 0.004 | A | 140 | C | 50 | A |
實施例18 | TMAH | H 2O | A | A | 3.0 | 0.006 | B | 170 | B | 40 | A |
實施例19 | CP | IPA | A | A | 2.9 | 0.007 | A | 150 | C | 40 | A |
實施例20 | TMAH | H 2O | A | A | 2.9 | 0.009 | A | 150 | C | 40 | A |
實施例21 | TMAH | H 2O | A | A | 2.8 | 0.005 | A | 150 | C | 50 | A |
實施例22 | TMAH | H 2O | A | A | 2.8 | 0.004 | A | 140 | C | 50 | A |
實施例23 | TMAH | H 2O | A | A | 3.1 | 0.009 | B | 200 | A | 40 | A |
實施例24 | TMAH | H 2O | A | A | 3.2 | 0.009 | B | 170 | B | 60 | A |
實施例25 | TMAH | H 2O | A | A | 2.9 | 0.007 | A | 210 | A | 50 | A |
比較例1 | TMAH | H 2O | A | A | 3.5 | 0.023 | E | 240 | A | 60 | A |
1a:剖面圖
1b:俯視圖
11:天線部
12:匹配電路
13:MSL供電線路
14:供電點
15,206:接地配線
16,210:絕緣膜
J:接地配線厚度
K:天線配線厚度
L:天線部之長度
M:匹配電路之長度
W:天線部之寬度
201:IC晶片
202:電極墊
203:第2通孔配線
204:平面天線配線
205:第2密封樹脂
207:第1通孔配線
208:第1密封樹脂
209:銅配線
211:障壁金屬
212:焊料凸塊
圖1(1a)及(1b)為共面供電型微波傳輸帶天線之概略圖。
圖2為與半導體封裝之剖面相關之概略圖。
Claims (15)
- 一種感光性樹脂組成物,其係含有(A)多官能單體、(B)黏合劑樹脂及(C)光聚合起始劑者,且該(A)多官能單體含有式(1)所表示之化合物及/或式(2)所表示之化合物,該(B)黏合劑樹脂含有自聚醯亞胺、聚醯亞胺前驅物、聚苯并 唑、聚苯并 唑前驅物、聚醯胺、該等之共聚合體、聚脲、聚酯、聚矽氧烷、丙烯酸系樹脂、酚樹脂、苯并環丁烯樹脂、順丁烯二酸樹脂及環烯烴聚合物所構成之群組選擇之1種以上, [化1] (式(1)中,W 1及W 2分別獨立地表示具有碳-碳雙鍵之包含碳數2~25之一價有機基;式(1)中,a、b、c及d分別獨立地為滿足a+b=6~17、c+d=8~19之自然數,虛線部意指碳-碳單鍵或碳-碳雙鍵) [化2] (式(2)中,W 3及W 4分別獨立地表示具有碳-碳雙鍵之包含碳數2~25之一價有機基;式(2)中,e、f、g及h分別獨立地為滿足e+f=5~16、g+h=8~19之自然數,虛線部意指碳-碳單鍵或碳-碳雙鍵)。
- 如請求項2之感光性樹脂組成物,其中,上述式(1)及上述式(2)中,W 1及W 2之至少一者以及W 3及W 4之至少一者為式(3)或式(4)所表示之基,且 上述式(3)及上述式(4)中,X及Y為-NH-。
- 如請求項5或6之感光性樹脂組成物,其中,上述(B)黏合劑樹脂進而含有具有聯苯構造之酚樹脂。
- 如請求項1至7中任一項之感光性樹脂組成物,其中,上述感光性樹脂組成物進而含有(D)交聯劑,該(D)交聯劑含有自環氧化合物、氧雜環丁烷化合物及羥甲基化合物所構成之群組選擇之一種以上。
- 如請求項8之感光性樹脂組成物,其中,上述(D)交聯劑含有羥甲基化合物。
- 一種硬化膜,其係使請求項1至9中任一項之感光性樹脂組成物硬化而成。
- 一種電子零件,其具有請求項10之硬化膜。
- 一種天線元件,其係至少具備1個以上之天線配線、及請求項10之硬化膜者,且該天線配線包含自彎折狀環形天線、線圈狀環形天線、彎折狀單極天線、彎折狀偶極天線或平面天線所構成之群組選擇之任一種以上,該天線配線中之每一個天線部之佔有面積為1000 mm 2以下,該硬化膜為使接地配線與天線配線間絕緣之絕緣膜。
- 一種半導體封裝,其係至少具備半導體元件、再配線層、密封樹脂及天線配線者,且該天線配線包含自彎折狀環形天線、線圈狀環形天線、彎折狀單極天線、彎折狀偶極天線及微波傳輸帶天線所構成之群組選擇之至少一種以上,該天線配線中之每一個天線部之佔有面積為1000 mm 2以下,該再配線層之絕緣層、及/或該密封樹脂包含請求項10之硬化膜,該密封樹脂位於接地配線與天線配線間。
- 如請求項11之電子零件,其係具備積層天線配線及請求項10之硬化膜而獲得之天線元件者,且天線配線之高度為50~200 μm,該硬化膜之厚度為80~300 μm。
- 一種化合物,其係由式(1)表示或由式(2)表示, [化7] (式(1)中,W 1及W 2分別獨立地表示式(3)或式(4)所表示之基;式(1)中,a、b、c及d分別獨立地為滿足a+b=6~17、c+d=8~19之自然數,虛線部意指碳-碳單鍵或碳-碳雙鍵) [化8] (式(2)中,W 3及W 4分別獨立地表示式(3)或式(4)所表示之基;式(2)中,e、f、g及h分別獨立地為滿足e+f=5~16、g+h=8~19之自然數,虛線部意指碳-碳單鍵或碳-碳雙鍵) [化9] (式(3)及式(4)中,X及Y表示-NH-;R 1表示單鍵或包含碳數1~5之二~六價有機基;R 2表示單鍵或包含碳數1~5之二價有機基;i表示1~5之整數;*表示鍵結點)。
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