TW202208486A - 環氧樹脂組成物、其硬化物、密封材、電路基板用材料、預浸體及積層板 - Google Patents
環氧樹脂組成物、其硬化物、密封材、電路基板用材料、預浸體及積層板 Download PDFInfo
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- TW202208486A TW202208486A TW110119881A TW110119881A TW202208486A TW 202208486 A TW202208486 A TW 202208486A TW 110119881 A TW110119881 A TW 110119881A TW 110119881 A TW110119881 A TW 110119881A TW 202208486 A TW202208486 A TW 202208486A
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- Prior art keywords
- epoxy resin
- resin composition
- phenol
- resin
- group
- Prior art date
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- 239000003822 epoxy resin Substances 0.000 title claims abstract description 128
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 128
- 239000000203 mixture Substances 0.000 title claims abstract description 55
- 229920005989 resin Polymers 0.000 claims abstract description 71
- 239000011347 resin Substances 0.000 claims abstract description 71
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 2
- 239000004848 polyfunctional curative Substances 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 239000000463 material Substances 0.000 claims description 14
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- 239000003795 chemical substances by application Substances 0.000 abstract description 20
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- 239000011889 copper foil Substances 0.000 abstract description 13
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 48
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 30
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- 230000000052 comparative effect Effects 0.000 description 23
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- 239000000126 substance Substances 0.000 description 17
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- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 16
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 16
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- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 12
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- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 6
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- 125000003277 amino group Chemical group 0.000 description 2
- ZRIUUUJAJJNDSS-UHFFFAOYSA-N ammonium phosphates Chemical class [NH4+].[NH4+].[NH4+].[O-]P([O-])([O-])=O ZRIUUUJAJJNDSS-UHFFFAOYSA-N 0.000 description 2
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- 125000003944 tolyl group Chemical group 0.000 description 1
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Abstract
Description
本發明是有關於一種低介電特性及高接著性優異的使用多元羥基樹脂的環氧樹脂組成物及其硬化物、預浸體(prepreg)、積層板、印刷配線基板。
環氧樹脂由於接著性、可撓性、耐熱性、耐化學品性、絕緣性、硬化反應性優異,因此於塗料、土木接著、注塑、電氣電子材料、膜材料等多方面中使用。尤其於作為電氣電子材料之一的印刷配線基板用途中,藉由對環氧樹脂賦予阻燃性而得到廣泛使用。
近年來,資訊設備的小型化、高性能化正在急速發展,與此相伴,對半導體或電子零件的領域中使用的材料,要求較以往更高的性能。尤其對於作為電氣電子零件的材料的環氧樹脂組成物,要求伴隨基板的薄型化及高功能化的低介電特性。
如下述專利文獻1所示,迄今為止,於積層板用途的低介電常數化中,一直使用導入有脂肪族骨架的二環戊二烯酚樹脂等,但於改善介電損耗正切方面效果不足,另外關於接著性,亦無法令人滿意。
作為用於獲得低介電損耗正切的樹脂,如下述專利文獻2所示,一直使用導入有芳香族骨架的芳香族改質環氧樹脂等,但於提供優異的介電損耗正切的同時,存在接著力惡化的課題,要求開發一種提供低介電損耗正切且高接著力的樹脂。
如上所述,任一文獻中揭示的環氧樹脂均未充分滿足近年來基於高功能化的要求性能,不足以確保低介電特性及接著性。
另一方面,專利文獻3揭示有一種2,6-二取代苯酚-二環戊二烯型樹脂組成物,但未揭示多個二環戊二烯在苯酚環進行取代的樹脂。
[現有技術文獻]
[專利文獻]
[專利文獻1]日本專利特開2001-240654號公報
[專利文獻2]日本專利特開2015-187190號公報
[專利文獻3]日本專利特開平5-339341號公報
因此,本發明所欲解決之課題在於提供一種於硬化物中顯現出優異的介電損耗正切、進而於印刷配線板用途中銅箔剝離強度及層間密接強度優異的硬化性樹脂組成物。
為解決所述課題,本發明者等人發現,當將使2,6-二取代苯酚類與特定比率的二環戊二烯反應而獲得的具有二環戊烯基的多元羥基樹脂與環氧樹脂硬化時,所獲得的硬化物的低介電特性及接著性優異,從而完成本發明。
即,本發明是一種環氧樹脂組成物,其含有環氧樹脂及硬化劑,且所述環氧樹脂組成物的特徵在於,硬化劑的一部分或全部為下述通式(1)所表示的多元羥基樹脂。
[化1](1)
此處,R1
獨立地表示碳數1~8的烴基,R2
獨立地表示氫原子或二環戊烯基,且至少一個為二環戊烯基。n表示重複數,其平均值為0~5的數。
所述多元羥基樹脂的羥基當量較佳為190 g/eq.~500 g/eq.。
另外,本發明是一種使所述環氧樹脂組成物硬化而成的硬化物,且是一種使用所述環氧樹脂組成物的密封材、預浸體、積層板或電路基板用材料。
本發明的環氧樹脂組成物提供一種於其硬化物中顯現出優異的介電損耗正切、進而於印刷配線板用途中銅箔剝離強度及層間密接強度優異的環氧樹脂組成物。尤其可較佳地用於強烈要求低介電損耗正切的行動(mobile)用途或伺服器(server)用途等中。
以下,對本發明的實施方式進行詳細說明。
本發明中使用的多元羥基樹脂(以下亦稱為酚樹脂)由所述通式(1)所表示。
通式(1)中,R1
獨立地表示碳數1~8的烴基,較佳為碳數1~8的烷基、碳數6~8的芳基、碳數7~8的芳烷基或烯丙基。作為碳數1~8的烷基,可為直鏈狀、分支狀、環狀的任一種,例如可列舉甲基、乙基、丙基、異丙基、正丁基、第三丁基、己基、環己基、甲基環己基等,但並不限定於該些。作為碳數6~8的芳基,可列舉苯基、甲苯基、二甲苯基、乙基苯基等,但並不限定於該些。作為碳數7~8的芳烷基,可列舉苄基、α-甲基苄基等,但並不限定於該些。於該些取代基中,就獲取的容易性及製成硬化物時的反應性的觀點而言,較佳為苯基、甲基,特佳為甲基。
R2
獨立地表示氫原子或二環戊烯基,至少一個為二環戊烯基。較佳為一分子中的R2
在每個苯酚環中,平均具有0.1個~1個二環戊烯基。二環戊烯基是源自二環戊二烯的基,由下述式(1a)或式(1b)所表示。由於該基的存在,本發明的環氧樹脂組成物的硬化物可降低介電常數、介電損耗正切。
[化2](1a)(1b)
n為重複數,表示0以上的數,其平均值(數量平均)為0~5,較佳為0.5~3,更佳為0.6~2,進而佳為0.6~1.8。作為藉由GPC而得的含量,較佳為n=0體為10面積%以下,n=1體為50面積%~80面積%,n=2體為20面積%~40面積%的範圍內。
多元羥基樹脂的分子量較佳為重量平均分子量(Mw)為400~1000、數量平均分子量(Mn)為350~800的範圍。
另外,酚性羥基當量(g/eq.)較佳為190~500,更佳為200~500,進而佳為220~400。
所述酚樹脂例如可藉由使下述通式(2)所表示的2,6-二取代苯酚類與二環戊二烯於三氟化硼-醚觸媒等路易斯酸存在下反應而獲得。
作為所述2,6-二取代苯酚類,可列舉2,6-二甲基苯酚、2,6-二乙基苯酚、2,6-二丙基苯酚、2,6-二異丙基苯酚、2,6-二(正丁基)苯酚、2,6-二(第三丁基)苯酚、2,6-二己基苯酚、2,6-二環己基苯酚、2,6-二苯基苯酚、2,6-二甲苯基苯酚、2,6-二苄基苯酚、2,6-雙(α-甲基苄基)苯酚、2-乙基-6-甲基苯酚、2-烯丙基-6-甲基苯酚、2-甲苯基-6-苯基苯酚等,就獲得的容易性及製成硬化物時的反應性的觀點而言,較佳為2,6-二苯基苯酚、2,6-二甲基苯酚,特佳為2,6-二甲基苯酚。
所述反應中使用的觸媒為路易斯酸,具體而言為三氟化硼、三氟化硼-酚錯合物、三氟化硼-醚錯合物、氯化鋁、氯化錫、氯化鋅、氯化鐵等,其中,就操作的容易度而言,較佳為三氟化硼-醚錯合物。於三氟化硼-醚錯合物的情況下,相對於二環戊二烯100質量份,觸媒的使用量為0.001質量份~20質量份,較佳為0.5質量份~10質量份。
作為用於向2,6-二取代苯酚類中導入所述式(1a)或所述式(1b)的二環戊二烯結構的反應方法,是使二環戊二烯以規定的比率與2,6-二取代苯酚反應的方法,亦可連續地添加二環戊二烯或以多階段間歇地進行反應。於一般的反應中,關於比率,相對於2,6-二取代苯酚1莫耳,二環戊二烯為0.1倍莫耳~0.25倍莫耳,但於本發明中為0.28倍莫耳~2.0倍莫耳,較佳為0.50倍莫耳~1.5倍莫耳,更佳為0.70倍莫耳~1.3倍莫耳。
關於連續添加二環戊二烯使其反應時的比率,相對於2,6-二取代苯酚,二環戊二烯較佳為0.28倍莫耳~1.0倍莫耳,更佳為0.3倍莫耳~0.5倍莫耳。於以多階段間歇地加入二環戊二烯使其反應的情況下,較佳為0.8倍莫耳~2倍莫耳,更佳為0.9倍莫耳~1.7倍莫耳。再者,各階段中的二環戊二烯的使用量較佳為0.28倍莫耳~1.0倍莫耳。
作為確認於所述通式(1)所表示的酚樹脂中導入有式(1a)或式(1b)所表示的取代基的方法,可使用質量分析法及傅立葉轉換紅外光譜(Fourier transform infrared spectroscopy,FT-IR)測定。
於使用質量分析方法的情況下,可使用電灑質量分析法(電灑游離質譜法(electrospray ionization mass spectrometry,ESI-MS))或場脫附法(場脫附質譜(field desorption mass spectrometry,FD-MS))等。藉由對利用GPC等將核體數不同的成分分離所得的樣品實施質量分析法,可確認導入有式(1a)或式(1b)所表示的取代基。
於使用FT-IR測定法的情況下,將溶解於四氫呋喃(tetrahydrofuran,THF)等有機溶劑中的樣品塗佈於KRS-5單元上,利用FT-IR來測定使有機溶劑乾燥而獲得的帶樣品薄膜的單元時,由苯酚核的C-O伸縮振動引起的波峰出現在1210 cm-1
附近,僅於導入有式(1a)或式(1b)的情況下,在3040 cm-1
附近出現由二環戊二烯骨架的烯烴部位的C-H伸縮振動引起的波峰。當將以直線形式連接目標波峰的起點與終點而得者設為基線、將自波峰的頂點至基線的長度設為峰高時,根據3040 cm-1
附近的波峰(A3040
)與1210 cm-1
附近的波峰(A1210
)的比率(A3040
/A1210
),可確定式(1a)或式(1b)的導入量。可確認到其比率越大物性值越良好,用以滿足目標物性的較佳比率(A3040
/A1210
)為0.05以上,更佳為0.10以上。上限值並無特別限定,但例如為0.50左右。
本反應適宜為將2,6-二取代苯酚類及觸媒裝入反應器中,歷時1小時~10小時滴加二環戊二烯的方式。
反應溫度較佳為50℃~200℃,更佳為100℃~180℃,進而佳為120℃~160℃。反應時間較佳為1小時~10小時,更佳為3小時~10小時,進而佳為4小時~8小時。
反應結束後,加入氫氧化鈉、氫氧化鉀、氫氧化鈣等鹼使觸媒失活。其後,加入甲苯、二甲苯等芳香族烴類或甲基乙基酮、甲基異丁基酮等酮類等的溶劑加以溶解,水洗後,於減壓下回收溶劑,藉此可獲得目標酚樹脂。再者,較佳為使二環戊二烯儘可能全部反應,使2,6-二取代苯酚類的一部分未反應、較佳為10%以下未反應,並將其減壓回收。
反應時,根據需要亦可使用苯、甲苯、二甲苯等芳香族烴類,或氯苯、二氯苯等鹵化烴類,或乙二醇二甲醚、二乙二醇二甲醚等醚類等的溶劑。
本發明的環氧樹脂組成物以環氧樹脂及硬化劑為必需成分,硬化劑為本發明的酚樹脂,且較佳為硬化劑中至少30質量%為所述通式(1)所表示的酚樹脂,更佳為含有50質量%以上。於較其更少的情況下,有介電特性惡化之虞。
作為為了獲得本發明的環氧樹脂組成物而使用的環氧樹脂,分子中具有兩個以上的環氧基的通常的環氧樹脂皆可使用。
若舉例,則可列舉:雙酚A型環氧樹脂、雙酚F型環氧樹脂、雙酚AF型環氧樹脂、四甲基雙酚F型環氧樹脂、對苯二酚型環氧樹脂、聯苯型環氧樹脂、二苯乙烯型環氧樹脂、雙酚芴型環氧樹脂、雙酚S型環氧樹脂、雙硫醚型環氧樹脂、間苯二酚型環氧樹脂、聯苯基芳烷基酚型環氧樹脂、萘二酚型環氧樹脂、苯酚酚醛清漆型環氧樹脂、芳香族改質苯酚酚醛清漆型環氧樹脂、甲酚酚醛清漆型環氧樹脂、烷基酚醛清漆型環氧樹脂、雙酚酚醛清漆型環氧樹脂、聯萘酚型環氧樹脂、萘酚酚醛清漆型環氧樹脂、β-萘酚芳烷基型環氧樹脂、二萘酚芳烷基型環氧樹脂、α-萘酚芳烷基型環氧樹脂、三苯基甲烷型環氧樹脂等三官能環氧樹脂、四苯基乙烷型環氧樹脂等四官能環氧樹脂、二環戊二烯型環氧樹脂、1,4-丁二醇二縮水甘油醚、1,6-己二醇二縮水甘油醚、甘油聚縮水甘油醚、三羥甲基丙烷聚縮水甘油醚、三羥甲基乙烷聚縮水甘油醚、季戊四醇聚縮水甘油醚等多元醇聚縮水甘油醚、丙二醇二縮水甘油醚等烷二醇型環氧樹脂、環己烷二甲醇二縮水甘油醚等脂肪族環狀環氧樹脂、二聚酸聚縮水甘油酯等縮水甘油酯類、苯基二縮水甘油胺、三-二縮水甘油胺、二胺基二苯基甲烷四縮水甘油胺、胺基苯酚型環氧樹脂等縮水甘油胺型環氧樹脂、賽羅西德(Celloxide)2021P(大賽璐(Daicel)股份有限公司製造)等脂環式環氧樹脂、含磷環氧樹脂、含溴環氧樹脂、胺基甲酸酯改質環氧樹脂、含噁唑啶酮環的環氧樹脂,但並不限定於該些。另外,該些環氧樹脂可單獨使用,亦可併用兩種以上。就獲取容易度的觀點而言,進而佳為使用下述通式(3)所表示的環氧樹脂、或二環戊二烯型環氧樹脂、萘二酚型環氧樹脂、苯酚酚醛清漆型環氧樹脂、芳香族改質苯酚酚醛清漆型環氧樹脂、甲酚酚醛清漆型環氧樹脂、α-萘酚芳烷基型環氧樹脂、二環戊二烯型環氧樹脂、含磷環氧樹脂、含噁唑啶酮環的環氧樹脂。
[化4](3)(4)
此處,R3
獨立地表示碳數1~8的烴基,例如為甲基、乙基、正丙基、異丙基、正丁基、第三丁基、正己基、環己基等烷基,彼此可相同亦可不同。
X表示二價基,例如表示亞甲基、伸乙基、伸異丙基、伸異丁基、六氟伸異丙基等伸烷基、-CO-、-O-、-S-、-SO2
-、-S-S-、或式(4)所表示的伸烷基。
R4
獨立地表示氫原子或碳數1以上的烴基,例如為甲基,彼此可相同亦可不同。
Ar為苯環或萘環,該些苯環或萘環可具有碳數1~10的烷基、碳數1~10的烷氧基、碳數6~11的芳基、碳數7~12的芳烷基、碳數6~11的芳氧基、或碳數7~12的芳烷基氧基作為取代基。
作為硬化劑,除所述通式(1)的多元羥基樹脂以外,根據需要亦可併用一種或兩種以上的各種酚樹脂類、酸酐類、胺類、氰酸酯類、活性酯類、醯肼類、酸性聚酯類、芳香族氰酸酯類等通常使用的硬化劑。於併用該些硬化劑的情況下,所併用的硬化劑較佳為全部硬化劑中的70質量%以下,更佳為50質量%以下。若所併用的硬化劑的比例過多,則作為環氧樹脂組成物的介電特性及接著特性有惡化之虞。
於本發明的環氧樹脂組成物中,相對於全部環氧樹脂的環氧基1莫耳,硬化劑的活性氫基的莫耳比較佳為0.2莫耳~1.5莫耳,更佳為0.3莫耳~1.4莫耳,進而佳為0.5莫耳~1.3莫耳,特佳為0.8莫耳~1.2莫耳。於超出該範圍的情況下,有硬化不完全而無法獲得良好的硬化物性之虞。例如,於使用酚樹脂系硬化劑或胺系硬化劑的情況下,相對於環氧基而調配大致等莫耳的活性氫基。於使用酸酐系硬化劑的情況下,相對於環氧基1莫耳而調配0.5莫耳~1.2莫耳、較佳為0.6莫耳~1.0莫耳的酸酐基。於單獨使用本發明的酚樹脂作為硬化劑的情況下,相對於環氧樹脂1莫耳,理想為以0.9莫耳~1.1莫耳的範圍使用。
本發明中所謂活性氫基是具有與環氧基具有反應性的活性氫的官能基(包含具有因水解等而產生活性氫的潛在性活性氫的官能基、或顯示同等的硬化作用的官能基),具體而言可列舉酸酐基或羧基或胺基或酚性羥基等。再者,關於活性氫基,1莫耳的羧基或酚性羥基算為1莫耳,胺基(NH2
)算為2莫耳。另外,於活性氫基並不明確的情況下,可藉由測定而求出活性氫當量。例如,可使環氧當量已知的苯基縮水甘油醚等單環氧樹脂與活性氫當量未知的硬化劑反應,測定所消耗的單環氧樹脂的量,藉此求出所使用的硬化劑的活性氫當量。
作為可併用的酚樹脂系硬化劑,具體例可列舉:雙酚A、雙酚F、雙酚C、雙酚K、雙酚Z、雙酚S、四甲基雙酚A、四甲基雙酚F、四甲基雙酚S、四甲基雙酚Z、四溴雙酚A、二羥基二苯硫醚、4,4'-硫代雙(3-甲基-6-第三丁基苯酚)等雙酚類,或兒茶酚、雷瑣辛(resorcin)、甲基雷瑣辛、對苯二酚、單甲基對苯二酚、二甲基對苯二酚、三甲基對苯二酚、單-第三丁基對苯二酚、二-第三丁基對苯二酚等二羥基苯類,或二羥基萘、二羥基甲基萘、二羥基甲基萘、三羥基萘等羥基萘類,或LC-950PM60(新安(Shin-AT&C)公司製造)等含磷酚硬化劑,或昭能(Shonol)BRG-555(愛克工業(Aica Kogyo)股份有限公司製造)等苯酚酚醛清漆樹脂、DC-5(日鐵化學&材料股份有限公司製造)等甲酚酚醛清漆樹脂、含三嗪骨架的酚樹脂、芳香族改質苯酚酚醛清漆樹脂、雙酚A酚醛清漆樹脂、樂吉拓(Resitop)TPM-100(群榮化學工業股份有限公司製造)等三羥基苯基甲烷型酚醛清漆樹脂、萘酚酚醛清漆樹脂等苯酚類、萘酚類及/或雙酚類與醛類的縮合物,SN-160、SN-395、SN-485(日鐵化學&材料股份有限公司製造)等苯酚類、苯酚類及/或萘酚類及/或雙酚類與伸二甲苯基二醇的縮合物,苯酚類及/或萘酚類與異丙烯基苯乙酮的縮合物,苯酚類及/或萘酚類及/或雙酚類與二環戊二烯的反應產物,苯酚類及/或萘酚類及/或雙酚類與二乙烯基苯的反應產物,苯酚類及/或萘酚類及/或雙酚類與萜烯類的反應產物,苯酚類及/或萘酚類及/或雙酚類與聯苯系交聯劑的縮合物等所謂的被稱為酚醛清漆酚樹脂的酚化合物、聚丁二烯改質酚樹脂、具有螺環的酚樹脂等。就獲取容易度的觀點而言,較佳為苯酚酚醛清漆樹脂、二環戊二烯型酚樹脂、三羥基苯基甲烷型酚醛清漆樹脂、芳香族改質苯酚酚醛清漆樹脂等。
於酚醛清漆酚樹脂的情況下,作為酚類,可列舉苯酚、甲酚、二甲酚、丁基苯酚、戊基苯酚、壬基苯酚、丁基甲基苯酚、三甲基苯酚、苯基苯酚等,作為萘酚類,可列舉1-萘酚、2-萘酚等,此外亦可列舉所述雙酚類。作為醛類,可例示甲醛、乙醛、丙醛、丁醛、戊醛、己醛、苯甲醛、氯醛、溴醛、乙二醛、丙二醛、丁二醛、戊二醛、己二醛、庚二醛、癸二醛、丙烯醛、巴豆醛、柳醛、鄰苯二甲醛、羥基苯甲醛等。作為聯苯系交聯劑,可列舉雙(羥甲基)聯苯、雙(甲氧基甲基)聯苯、雙(乙氧基甲基)聯苯、雙(氯甲基)聯苯等。
作為可併用的酸酐系硬化劑,具體而言可列舉:馬來酸酐、甲基四氫鄰苯二甲酸酐、六氫鄰苯二甲酸酐、4-甲基六氫鄰苯二甲酸酐、甲基雙環[2.2.1]庚烷-2,3-二羧酸酐、雙環[2.2.1]庚烷-2,3-二羧酸酐、1,2,3,6-四氫鄰苯二甲酸酐、均苯四甲酸酐、鄰苯二甲酸酐、偏苯三甲酸酐、甲基納迪克酸、苯乙烯單體與馬來酸酐的共聚物、茚類與馬來酸酐的共聚物等。
作為可併用的胺系硬化劑,具體而言可列舉:二乙三胺、三乙四胺、間苯二甲胺、異佛爾酮二胺、二胺基二苯基甲烷、二胺基二苯基碸、二胺基二苯基醚、苄基二甲胺、2,4,6-三(二甲基胺基甲基)苯酚、聚醚胺、雙胍化合物、二氰二胺、甲氧苯胺(anisidine)等芳香族胺類、作為二聚酸等酸類與多胺類的縮合物的聚醯胺胺等胺系化合物等。
作為可併用的氰酸酯化合物,只要是一分子中具有兩個以上的氰酸基(氰酸酯基)的化合物則並無特別限定。例如,可列舉:苯酚酚醛清漆型、烷基苯酚酚醛清漆型等酚醛清漆型氰酸酯系硬化劑,萘酚芳烷基型氰酸酯系硬化劑,聯苯烷基型氰酸酯系硬化劑,二環戊二烯型氰酸酯系硬化劑,雙酚A型、雙酚F型、雙酚E型、四甲基雙酚F型、雙酚S型等雙酚型氰酸酯系硬化劑,以及該些的一部分三嗪化的預聚物等。作為氰酸酯系硬化劑的具體例,例如可列舉:雙酚A二氰酸酯、多酚氰酸酯(寡聚(3-亞甲基-1,5-伸苯基氰酸酯)、雙(3-甲基-4-氰酸酯苯基)甲烷、雙(3-乙基-4-氰酸酯苯基)甲烷、雙(4-氰酸酯苯基)-1,1-乙烷、4,4-二氰酸酯-二苯基酯、2,2-雙(4-氰酸酯苯基)-1,1,1,3,3,3-六氟丙烷、4,4'-亞甲基雙(2,6-二甲基苯基氰酸酯)、4,4'-亞乙基二苯基二氰酸酯、六氟雙酚A二氰酸酯、2,2-雙(4-氰酸酯)苯基丙烷、1,1-雙(4-氰酸酯苯基甲烷)、雙(4-氰酸酯-3,5-二甲基苯基)甲烷、1,3-雙(4-氰酸酯苯基-1-(甲基亞乙基))苯、雙(4-氰酸酯苯基)硫醚、雙(4-氰酸酯苯基)醚等二官能氰酸酯樹脂,三(4-氰酸酯苯基)-1,1,1-乙烷、雙(3,5-二甲基-4-氰酸酯苯基)-4-氰酸酯苯基-1,1,1-乙烷等三元酚的氰酸酯,自苯酚酚醛清漆、甲酚酚醛清漆、含二環戊二烯結構的酚樹脂等衍生的多官能氰酸酯樹脂、該些氰酸酯樹脂的一部分三嗪化的預聚物等。該些可使用一種或兩種以上。
作為可併用的活性酯系硬化劑,並無特別限制,但一般較佳為使用苯酚酯類、苯硫酚酯類、N-羥基胺酯類、雜環羥基化合物的酯類等於一分子中具有兩個以上的反應活性高的酯基的化合物。該活性酯系硬化劑較佳為藉由羧酸化合物及/或硫代羧酸化合物與羥基化合物及/或硫醇化合物的縮合反應而獲得。特別是就耐熱性提高的觀點而言,較佳為由羧酸化合物與羥基化合物獲得的活性酯系硬化劑,更佳為由羧酸化合物與苯酚化合物及/或萘酚化合物獲得的活性酯系硬化劑。作為羧酸化合物,例如可列舉苯甲酸、乙酸、琥珀酸、馬來酸、衣康酸、鄰苯二甲酸、間苯二甲酸、對苯二甲酸、均苯四甲酸等。作為苯酚化合物或萘酚化合物,例如可列舉:對苯二酚、間苯二酚、雙酚A、雙酚F、雙酚S、酸式酚酞(phenolphthalin)、甲基化雙酚A、甲基化雙酚F、甲基化雙酚S、苯酚、鄰甲酚、間甲酚、對甲酚、兒茶酚、α-萘酚、β-萘酚、1,5-二羥基萘、1,6-二羥基萘、2,6-二羥基萘、二羥基二苯甲酮、三羥基二苯甲酮、四羥基二苯甲酮、間苯三酚(phloroglucin)、苯三酚、二環戊二烯基二苯酚、苯酚酚醛清漆、含二環戊二烯結構的酚樹脂等。活性酯系硬化劑可使用一種或兩種以上。作為活性酯系硬化劑,具體而言較佳為包含二環戊二烯二苯酚結構的活性酯系硬化劑、包含萘結構的活性酯系硬化劑、作為苯酚酚醛清漆的乙醯基化物的活性酯系硬化劑、作為苯酚酚醛清漆的苯甲醯基化物的活性酯系硬化劑等,其中,就剝離強度的提高優異的方面而言,更佳為包含本發明的環氧樹脂的前驅物的包含二環戊二烯二苯酚結構的活性酯系硬化劑。
作為其他可併用的硬化劑,具體而言可列舉:三苯基膦等膦化合物,四苯基溴化鏻等鏻鹽,2-甲基咪唑、2-苯基咪唑、2-乙基-4-甲基咪唑、2-十一烷基咪唑、1-氰基乙基-2-甲基咪唑等咪唑類,作為咪唑類與偏苯三甲酸、異氰脲酸或硼等的鹽的咪唑鹽類,三甲基氯化銨等四級銨鹽類,二氮雜雙環化合物,二氮雜雙環化合物與苯酚類或苯酚酚醛清漆樹脂類等的鹽類,三氟化硼與胺類或醚化合物等的錯合化合物,芳香族鏻鹽或芳香族碘鎓鹽等。
環氧樹脂組成物中可根據需要而使用硬化促進劑。作為可使用的硬化促進劑的例子,可列舉:2-甲基咪唑、2-乙基咪唑、2-乙基-4-甲基咪唑等咪唑類,4-二甲基胺基吡啶、2-(二甲基胺基甲基)苯酚、1,8-二氮雜-雙環(5,4,0)十一烯-7等三級胺類,三苯基膦、三環己基膦、三苯基膦三苯基硼烷等膦類,辛酸錫等金屬化合物。於使用硬化促進劑的情況下,相對於本發明的環氧樹脂組成物中的環氧樹脂成分100質量份,硬化促進劑的使用量較佳為0.02質量份~5質量份。藉由使用硬化促進劑,可降低硬化溫度、或縮短硬化時間。
環氧樹脂組成物中可使用有機溶劑或反應性稀釋劑來用於調整黏度。
作為有機溶劑,例如可列舉:N,N-二甲基甲醯胺、N,N-二甲基乙醯胺等醯胺類,或乙二醇單甲醚、二甲氧基二乙二醇、乙二醇二***、二乙二醇二***、三乙二醇二甲醚等醚類,或丙酮、甲基乙基酮、甲基異丁基酮、環己酮等酮類,或甲醇、乙醇、1-甲氧基-2-丙醇、2-乙基-1-己醇、苄醇、乙二醇、丙二醇、丁基二乙二醇、松油等醇類,或乙酸丁酯、乙酸甲氧基丁酯、甲基賽路蘇乙酸酯、乙基賽路蘇乙酸酯、乙基二乙二醇乙酸酯、丙二醇單甲醚乙酸酯、卡必醇乙酸酯、苄醇乙酸酯等乙酸酯類,或苯甲酸甲酯、苯甲酸乙酯等苯甲酸酯類,或甲基賽路蘇、乙基賽路蘇、丁基賽路蘇等賽路蘇類,或甲基卡必醇、乙基卡必醇、丁基卡必醇等卡必醇類,或苯、甲苯、二甲苯等芳香族烴類,或二甲基亞碸、乙腈、N-甲基吡咯啶酮等,但並不限定於該些。
作為反應性稀釋劑,例如可列舉:烯丙基縮水甘油醚、丁基縮水甘油醚、2-乙基己基縮水甘油醚、苯基縮水甘油醚、甲苯基縮水甘油醚等單官能縮水甘油醚類,或新癸烷酸縮水甘油酯等單官能縮水甘油酯類等,但並不限定於該些。
該些有機溶劑或反應性稀釋劑較佳為於樹脂組成物中以不揮發成分為90質量%以下而單獨使用或使用混合有多種者,其適當的種類或使用量可根據用途而適宜選擇。例如於印刷配線板用途中,較佳為甲基乙基酮、丙酮、1-甲氧基-2-丙醇等沸點為160℃以下的極性溶劑,樹脂組成物中的使用量以不揮發成分計較佳為40質量%~80質量%。另外,於接著膜用途中,例如較佳為使用酮類、乙酸酯類、卡必醇類、芳香族烴類、二甲基甲醯胺、二甲基乙醯胺、N-甲基吡咯啶酮等,其使用量以不揮發成分計較佳為30質量%~60質量%。
環氧樹脂組成物亦可在不損及特性的範圍內調配其他熱硬化性樹脂、熱塑性樹脂。例如可列舉:酚樹脂、苯並噁嗪樹脂、雙馬來醯亞胺樹脂、雙馬來醯亞胺三嗪樹脂、丙烯酸樹脂、石油樹脂、茚樹脂、苯並呋喃茚(coumarone indene)樹脂、苯氧基樹脂、聚胺基甲酸酯樹脂、聚酯樹脂、聚醯胺樹脂、聚醯亞胺樹脂、聚醯胺醯亞胺樹脂、聚醚醯亞胺樹脂、聚苯醚樹脂、改質聚苯醚樹脂、聚醚碸樹脂、聚碸樹脂、聚醚醚酮樹脂、聚苯硫醚樹脂、聚乙烯縮甲醛(polyvinyl formal)樹脂、聚矽氧烷化合物、含羥基的聚丁二烯等含反應性官能基的伸烷基樹脂類,但並不限定於該些。
為了提高所得的硬化物的阻燃性,環氧樹脂組成物中可使用公知的各種阻燃劑。作為可使用的阻燃劑,例如可列舉鹵素系阻燃劑、磷系阻燃劑、氮系阻燃劑、矽酮系阻燃劑、無機系阻燃劑、有機金屬鹽系阻燃劑等。就對環境的觀點而言,較佳為不含鹵素的阻燃劑,特佳為磷系阻燃劑。該些阻燃劑可單獨使用,亦可併用兩種以上。
磷系阻燃劑可使用無機磷系化合物、有機磷系化合物的任一種。作為無機磷系化合物,例如可列舉紅磷、磷酸一銨、磷酸二銨、磷酸三銨、多磷酸銨等磷酸銨類,磷酸醯胺等無機系含氮磷化合物。作為有機磷系化合物,例如可列舉脂肪族磷酸酯、磷酸酯化合物、例如PX-200(大八化學工業股份有限公司製造)等縮合磷酸酯類、聚磷腈(polyphosphazene)、膦酸化合物、次膦酸化合物、氧化膦化合物、正膦(phosphorane)化合物、有機系含氮磷化合物等通用有機磷系化合物,或次膦酸的金屬鹽,除此以外可列舉9,10-二氫-9-氧雜-10-磷雜菲-10-氧化物、10-(2,5-二羥基苯基)-10H-9-氧雜-10-磷雜菲-10-氧化物、10-(2,7-二羥基萘基)-10H-9-氧雜-10-磷雜菲-10-氧化物等環狀有機磷化合物,或作為使該些化合物與環氧樹脂或酚樹脂等化合物反應而得的衍生物的含磷環氧樹脂或含磷硬化劑等。
作為阻燃劑的調配量,可根據磷系阻燃劑的種類、環氧樹脂組成物的成分、所期望的阻燃性的程度而適宜選擇。例如,環氧樹脂組成物中的有機成分(有機溶劑除外)中的磷含量較佳為0.2質量%~4質量%,更佳為0.4質量%~3.5質量%,進而佳為0.6質量%~3質量%。若磷含量少,則有難以確保阻燃性之虞,若過多,則有對耐熱性造成不良影響之虞。另外,於使用磷系阻燃劑的情況下,亦可併用氫氧化鎂等阻燃助劑。
環氧樹脂組成物中可根據需要而使用填充劑。具體而言可列舉:熔融二氧化矽、結晶二氧化矽、氧化鋁、氮化矽、氫氧化鋁、水鋁石(boehmite)、氫氧化鎂、滑石、雲母、碳酸鈣、矽酸鈣、氫氧化鈣、碳酸鎂、碳酸鋇、硫酸鋇、氮化硼、碳、碳纖維、玻璃纖維、氧化鋁纖維、二氧化矽氧化鋁纖維、碳化矽纖維、聚酯纖維、纖維素纖維、芳族聚醯胺纖維、陶瓷纖維、微粒子橡膠、矽酮橡膠、熱塑性彈性體、碳黑、顏料等。作為使用填充劑的理由,一般可列舉耐衝擊性的提高效果。另外,於使用氫氧化鋁、水鋁石、氫氧化鎂等金屬氫氧化物的情況下,具有作為阻燃助劑起作用而阻燃性提高的效果。相對於環氧樹脂組成物整體,該些填充劑的調配量較佳為1質量%~150質量%,更佳為10質量%~70質量%。若調配量多,則有作為積層板用途而所需的接著性降低之虞,進而有硬化物變脆而無法獲得充分的機械物性之虞。另外,若調配量少,則有無法發揮硬化物的耐衝擊性提高等調配填充劑的效果之虞。
於將環氧樹脂組成物製成板狀基板等的情況下,就其尺寸穩定性、彎曲強度等方面而言,可列舉纖維狀者作為較佳的填充劑。更佳為列舉將玻璃纖維編為網狀的玻璃纖維基板。
環氧樹脂組成物可進一步根據需要而調配矽烷偶合劑、抗氧化劑、脫模劑、消泡劑、乳化劑、觸變性賦予劑、平滑劑、阻燃劑、顏料等各種添加劑。相對於環氧樹脂組成物,該些添加劑的調配量較佳為0.01質量%~20質量%的範圍。
環氧樹脂組成物可藉由含浸於纖維狀基材中而製成印刷配線板等中所使用的預浸體。作為纖維狀基材,可使用玻璃等無機纖維,或聚酯樹脂等、多胺樹脂、聚丙烯酸樹脂、聚醯亞胺樹脂、芳香族聚醯胺樹脂等有機質纖維的織布或不織布,但並不限定於此。作為由環氧樹脂組成物製造預浸體的方法,並無特別限定,例如是於將環氧樹脂組成物浸漬並含浸於利用有機溶劑調整黏度而製成的樹脂清漆中後,進行加熱乾燥而使樹脂成分半硬化(B階段化),獲得預浸體,例如可於100℃~200℃下加熱乾燥1分鐘~40分鐘。此處,預浸體中的樹脂量較佳為樹脂成分為30質量%~80質量%。
另外,為了使預浸體硬化,可使用一般製造印刷配線板時所使用的積層板的硬化方法,但並不限定於此。例如,於使用預浸體形成積層板的情況下,積層一片或多片預浸體,在單側或兩側配置金屬箔而構成積層物,對該積層物進行加熱、加壓而使其積層一體化。此處,作為金屬箔,可單獨使用銅、鋁、黃銅、鎳等,且可使用合金、複合的金屬箔。而且,可藉由對所製成的積層物進行加壓加熱而使預浸體硬化,獲得積層板。此時,較佳的是將加熱溫度設為160℃~220℃,將加壓壓力設為50 N/cm2
~500 N/cm2
,將加熱加壓時間設為40分鐘~240分鐘,從而可獲得目標硬化物。若加熱溫度低,則硬化反應不能充分進行,若加熱溫度高,則有環氧樹脂組成物開始分解之虞。另外,若加壓壓力低,則有在所得的積層板的內部殘留氣泡,電氣特性降低的情況,若加壓壓力高,則有樹脂在硬化前流動,無法獲得所希望厚度的硬化物之虞。進而,若加熱加壓時間短,則有不能充分進行硬化反應之虞,若加熱加壓時間長,則有引起預浸體中的環氧樹脂組成物的熱分解之虞,因而欠佳。
環氧樹脂組成物可藉由利用與公知的環氧樹脂組成物同樣的方法進行硬化而獲得環氧樹脂硬化物。作為用以獲得硬化物的方法,可採用與公知的環氧樹脂組成物同樣的方法,可適宜使用注塑、注入、灌注(potting)、浸漬、滴落塗佈(drip coating)、轉印成形、壓縮成形等或藉由製成樹脂片、帶有樹脂的銅箔、預浸體等形態進行積層並加熱加壓硬化而製成積層板等的方法。此時的硬化溫度通常為100℃~300℃,硬化時間通常為1小時~5小時左右。
本發明的環氧樹脂硬化物可採用積層物、成型物、接著物、塗膜、膜等形態。
製作環氧樹脂組成物,並藉由加熱硬化來評價積層板及硬化物,結果可提供於硬化物中顯現出優異的低介電特性、進而於印刷配線板用途中銅箔剝離強度及層間密接強度優異的環氧硬化性樹脂組成物。
[實施例]
列舉實施例及比較例來對本發明進行具體說明,但本發明並不限定於該些。只要並無特別說明,則「份」表示質量份,「%」表示質量%,「ppm」表示質量ppm。另外,測定方法是分別藉由以下的方法進行測定。
・羥基當量:
依據日本工業標準(Japanese Industrial Standards,JIS)K 0070標準進行測定,單位以「g/eq.」來表示。再者,只要並無特別說明,則酚樹脂的羥基當量是指酚性羥基當量。
・軟化點:
依據JIS K 7234標準、環球法進行測定。具體而言,使用自動軟化點裝置(明達科(Meitec)股份有限公司製造,ASP-MG4)。
・環氧當量:
依據JIS K 7236標準進行測定,單位以「g/eq.」來表示。具體而言,使用自動電位差滴定裝置(平沼產業股份有限公司製造,COM-1600ST),且使用氯仿作為溶劑,加入四乙基溴化銨乙酸溶液,利用0.1 mol/L過氯酸-乙酸溶液進行滴定。
・銅箔剝離強度及層間接著力:
依據JIS C 6481進行測定,層間接著力是在第7層與第8層之間進行剝離測定。
・相對介電常數及介電損耗正切:
依據IPC-TM-650 2.5.5.9,使用材料分析儀(material analyzer)(安捷倫科技(AGILENT Technologies)公司製造),藉由電容法求出頻率1 GHz下的相對介電常數及介電損耗正切,藉此進行評價。
・阻燃性:
依據美國保險商實驗室(Underwriters Laboratories,UL)94,藉由垂直法進行評價。評價以V-0、V-1、V-2(三階段評價)進行記載。
・玻璃轉移溫度(Tg):
由依據印刷電路協會(Institute of Printed Circuits,IPC)-TM-650 2.4.25.c,利用差示掃描量熱裝置(日立高科技科學股份有限公司製造,EXSTAR6000 DSC6200)在20℃/分鐘的升溫條件下進行測定時的DSC・Tgm(相對於玻璃狀態與橡膠狀態的切線而言的變異曲線的中間溫度)的溫度來表示。
・相對介電常數及介電損耗正切:
依據IPC-TM-650 2.5.5.9,使用材料分析儀(material analyzer)(安捷倫科技(AGILENT Technologies)公司製造),藉由電容法求出頻率1 GHz下的相對介電常數及介電損耗正切,藉此進行評價。
・GPC(凝膠滲透層析法)測定:
使用在本體(東曹(Tosoh)股份有限公司製造的HLC-8220GPC)中串列地包含管柱(東曹股份有限公司製造的TSKgelG4000HXL
、TSKgelG3000HXL
、TSKgelG2000HXL
)的裝置,管柱溫度設為40℃。另外,溶離液使用四氫呋喃(THF),流速設為1 mL/分鐘,檢測器使用示差折射率檢測器。測定試樣是使用50 μL的將樣品0.1 g溶解於10 mL的THF中並利用微濾器(microfilter)進行過濾而得者。資料處理是使用東曹股份有限公司製造的GPC-8020型號II版本6.00。
・IR:
使用傅立葉轉換型紅外分光光度計(珀金埃爾默精確(Perkin Elmer Precisely)製造,Spectrum One FT-IR Spectrometer 1760X),單元使用KRS-5,將溶解於THF中的樣品塗佈於單元上,使其乾燥後,測定波數650 cm-1
~4000 cm-1
的吸光度。
・ESI-MS:使用質量分析儀(島津製作所製造,LCMS-2020),作為流動相使用乙腈及水,測定溶解於乙腈中的樣品,藉此進行質量分析。
實施例、比較例中使用的簡稱如下。
[環氧樹脂]
E1:二環戊二烯型環氧樹脂(迪愛生(DIC)股份有限公司製造,HP-7200H,環氧當量280,軟化點82℃)
E2:鄰甲酚酚醛清漆型環氧樹脂(日鐵化學&材料股份有限公司製造,YDCN-700-3,環氧當量203,軟化點73℃)
E3:苯酚酚醛清漆型環氧樹脂(日鐵化學&材料股份有限公司製造,YDPN-638,環氧當量177)
E4:聯苯芳烷基型環氧樹脂(日本化藥股份有限公司製造,NC-3000,環氧當量274,軟化點60℃)
E5:三苯酚甲烷型環氧樹脂(日本化藥股份有限公司製造,EPPN-501H,環氧當量166)
E6:萘型環氧樹脂(日鐵化學&材料股份有限公司製造,ESN-475V,環氧當量325)
E7:含磷環氧樹脂(日鐵化學&材料股份有限公司製造,FX-1225,環氧當量317)
E8:聯苯型環氧樹脂(三菱化學股份有限公司製造,YX-4000H,環氧當量195,熔點105℃)
E9:含硫原子的環氧樹脂(日鐵化學&材料股份有限公司製造,YSLV-120TE,環氧當量250,熔點121℃)
E10:對苯二酚型環氧樹脂(日鐵化學&材料股份有限公司製造,YDC-1312,環氧當量176,熔點142℃)
[硬化劑]
P1:合成例1中得到的多元羥基樹脂
P2:合成例2中得到的多元羥基樹脂
P3:合成例3中得到的多元羥基樹脂
P4:二環戊二烯型酚樹脂(群榮化學工業股份有限公司製造,GDP-6140,羥基當量196,軟化點130℃)
P5:酚樹脂(群榮化學工業股份有限公司製造,樂吉拓(Resitop)TPM-100,羥基當量98,軟化點108℃)
P6:聯苯芳烷基型酚樹脂(明和化成股份有限公司製造,MEH-7851,羥基當量223,軟化點75℃)
P7:苯酚酚醛清漆樹脂(愛克SDK酚(Aica SDK phenol)股份有限公司製造,BRG-557,羥基當量105,軟化點85℃)
P8:二氰二胺(日本碳化物工業股份有限公司製造,迪哈德(DIHARD),活性氫當量21)
[苯並噁嗪樹脂]
B1:BPF型苯並噁嗪樹脂(四國化成工業股份有限公司製造,F-a型苯並噁嗪樹脂)
[硬化促進劑]
C1:2-乙基-4-甲基咪唑(四國化成工業股份有限公司製造,固唑(Curezol)2E4MZ)
C2:三苯基膦(北興化學工業股份有限公司製造,北興(Hokko)TPP)(日本專利特開平1-105562)
C3:2-苯基咪唑(四國化成工業股份有限公司製造,固唑(Curezol)2PZ)
[填充劑]
F1:中空玻璃填料(日本3M股份有限公司製造,玻璃殼(glass bulbs)iM30K,平均粒徑(d50)16 μm)
合成例1
向具備攪拌機、溫度計、氮氣吹入管、滴液漏斗及冷卻管的反應裝置中裝入2,6-二甲酚140份、47%BF3
醚錯合物9.3份(相對於最初添加的二環戊二烯為0.1倍莫耳),一邊攪拌一邊加溫至110℃。在保持為相同溫度的同時,用1小時滴加二環戊二烯86.6份(相對於2,6-二甲酚為0.57倍莫耳)。進而於110℃的溫度下反應3小時後,在保持為相同溫度的同時,用1小時滴加二環戊二烯68份(相對於2,6-二甲酚為0.44倍莫耳)。進而於120℃下反應2小時。加入氫氧化鈣14.6份。進而添加10%的草酸水溶液45份。其後,加溫至160℃進行脫水後,於5 mmHg的減壓下,加溫至200℃而將未反應的原料蒸發除去。加入700份的MIBK來溶解生成物,加入80℃的溫水200份來進行水洗,分離除去下層的水層。其後,於5 mmHg的減壓下,加溫至160℃而將MIBK蒸發除去,獲得274份的紅褐色的多元羥基樹脂(P1)。羥基當量為299,為軟化點97℃的樹脂,吸收比(A3040
/A1210
)為0.17。測定由ESI-MS(負)所得的質譜,結果確認到M-
=253、375、507、629。將所獲得的多元羥基樹脂(P1)的GPC示於圖1中,將FT-IR示於圖2中。GPC中的Mw為690,Mn為510,n=0體含量為6.5面積%,n=1體含量為61.5面積%,n=2體以上的含量為32.0面積%。圖1的a表示通式(1)的n=1體與通式(1)的不存在R2
加成體的n=1體的混合體,b表示通式(1)的n=0體。圖2的c表示由二環戊二烯骨架的烯烴部位的C-H伸縮振動引起的波峰,d表示由苯酚核的C-O伸縮振動引起的吸收。
合成例2
向與合成例1同樣的反應裝置中裝入2,6-二甲酚140份、47%BF3
醚錯合物9.3份(相對於最初添加的二環戊二烯為0.1倍莫耳),一邊攪拌一邊加溫至110℃。在保持為相同溫度的同時,用1小時滴加二環戊二烯86.6份(相對於2,6-二甲酚為0.57倍莫耳)。進而於110℃的溫度下反應3小時後,在保持為相同溫度的同時,用1小時滴加二環戊二烯90.6份(相對於2,6-二甲酚為0.60倍莫耳)。進而於120℃下反應2小時。加入氫氧化鈣14.6份。進而添加10%的草酸水溶液45份。其後,加溫至160℃進行脫水後,於5 mmHg的減壓下,加溫至200℃而將未反應的原料蒸發除去。加入740份的MIBK來溶解生成物,加入80℃的溫水200份來進行水洗,分離除去下層的水層。其後,於5 mmHg的減壓下,加溫至160℃而將MIBK蒸發除去,獲得310份的紅褐色的多元羥基樹脂(P2)。羥基當量為341,為軟化點104℃的樹脂,吸收比(A3040
/A1210
)為0.27。測定由ESI-MS(負)所得的質譜,結果確認到M-
=253、375、507、629。GPC中的Mw為830,Mn為530,n=0體含量為5.9面積%,n=1體含量為60.1面積%,n=2體以上的含量為34.0面積%。
合成例3
向與合成例1同樣的反應裝置中裝入2,6-二甲酚140份、47%BF3
醚錯合物9.3份(相對於最初添加的二環戊二烯為0.1倍莫耳),一邊攪拌一邊加溫至110℃。在保持為相同溫度的同時,用1小時滴加二環戊二烯86.6份(相對於2,6-二甲酚為0.57倍莫耳)。進而於110℃的溫度下反應3小時後,在保持為相同溫度的同時,用1小時滴加二環戊二烯34.0份(相對於2,6-二甲酚為0.22倍莫耳)。進而於120℃下反應2小時。加入氫氧化鈣14.6份。進而添加10%的草酸水溶液45份。其後,加溫至160℃進行脫水後,於5 mmHg的減壓下,加溫至200℃而將未反應的原料蒸發除去。加入608份的MIBK來溶解生成物,加入80℃的溫水200份來進行水洗,分離除去下層的水層。其後,於5 mmHg的減壓下,加溫至160℃而將MIBK蒸發除去,獲得253份的紅褐色的多元羥基樹脂(P3)。羥基當量為243,為軟化點92℃的樹脂,吸收比(A3040
/A1210
)為0.11。測定由ESI-MS(負)所得的質譜,結果確認到M-
=253、375、507、629。GPC中的Mw為460,Mn為380,n=0體含量為5.6面積%,n=1體含量為66.4面積%,n=2體以上的含量為28.0面積%。
實施例1
調配作為環氧樹脂的100份的E1、作為硬化劑的107份的P1、作為硬化促進劑的0.25份的C1,溶解於利用甲基乙基酮(Methyl Ethyl Ketone,MEK)、丙二醇單甲醚、N,N-二甲基甲醯胺進行了調整的混合溶劑中,獲得環氧樹脂組成物清漆。將所獲得的環氧樹脂組成物清漆含浸於玻璃布(日東紡績股份有限公司製造,WEA 7628 XS13,厚度0.18 mm)中。將已進行含浸的玻璃布於150℃的熱風循環烘箱中乾燥9分鐘,獲得預浸體。將所獲得的預浸體8片與銅箔(三井金屬礦業股份有限公司製造,3EC-III,厚度35 μm)上下重疊,於130℃×15分鐘+190℃×80分鐘的溫度條件下進行2 MPa的真空壓製,獲得厚度1.6 mm的積層板。將積層板的銅箔剝離強度、層間接著力及Tg的測定結果示於表1中。
另外,將所獲得的預浸體拆開,製成通過100目的篩的粉狀的預浸體粉末。將所獲得的預浸體粉末放入氟樹脂製的模具中,於130℃×15分鐘+190℃×80分鐘的溫度條件下進行2 MPa的真空壓製,獲得50 mm見方×2 mm厚的試驗片。將試驗片的相對介電常數及介電損耗正切的測定結果示於表1中。
實施例2~實施例11、比較例1~比較例11
以表1~表3的調配量(份)調配,進行與實施例1同樣的操作,獲得積層板及試驗片。硬化促進劑的使用量設為可將清漆凝膠時間調整為300秒左右的量。進行與實施例1同樣的試驗,將其結果示於表1~表3中。
[表1]
實施例1 | 實施例2 | 實施例3 | 比較例1 | 比較例2 | 比較例3 | 比較例4 | 比較例5 | |
E1 | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 100 |
P1 | 107 | |||||||
P2 | 122 | |||||||
P3 | 87 | |||||||
P4 | 70 | |||||||
P5 | 35 | |||||||
P6 | 80 | |||||||
P7 | 38 | |||||||
P8 | 3.8 | |||||||
C1 | 0.25 | 0.22 | 0.26 | 0.15 | 0.09 | 0.14 | 0.10 | |
銅箔剝離強度 (kN/m) | 1.5 | 1.3 | 1.5 | 1.6 | 1.5 | 1.6 | 1.6 | 1.5 |
層間接著力 (kN/m) | 1.2 | 1.1 | 1.3 | 1.2 | 1.1 | 1.2 | 1.2 | 1.0 |
相對介電常數 | 2.89 | 2.80 | 2.93 | 3.07 | 3.17 | 3.08 | 3.17 | 3.02 |
介電損耗正切 | 0.012 | 0.010 | 0.014 | 0.020 | 0.022 | 0.019 | 0.021 | 0.018 |
Tg(℃) | 160 | 155 | 167 | 172 | 195 | 132 | 184 | 200 |
[表2]
實施例4 | 實施例5 | 實施例6 | 實施例7 | 實施例8 | 比較例6 | 比較例7 | 比較例8 | |
E2 | 100 | |||||||
E3 | 100 | 100 | ||||||
E4 | 100 | 100 | ||||||
E5 | 100 | |||||||
E6 | 100 | 100 | ||||||
P1 | 147 | 169 | 109 | 180 | 92 | |||
P7 | 59 | 38 | 32 | |||||
C1 | 0.25 | 0.25 | 0.30 | 0.15 | 0.25 | 0.10 | 0.10 | 0.15 |
銅箔剝離強度 (kN/m) | 1.2 | 1.3 | 1.5 | 1.1 | 1.4 | 1.3 | 1.6 | 1.5 |
層間接著力 (kN/m) | 0.8 | 1.0 | 1.3 | 0.9 | 1.2 | 1.1 | 1.3 | 1.3 |
相對介電常數 | 3.05 | 2.99 | 2.95 | 2.91 | 2.94 | 3.27 | 3.21 | 3.23 |
介電損耗正切 | 0.015 | 0.015 | 0.009 | 0.015 | 0.008 | 0.024 | 0.016 | 0.011 |
Tg(℃) | 160 | 155 | 141 | 180 | 123 | 169 | 154 | 132 |
[表3]
實施例9 | 實施例10 | 實施例11 | 比較例9 | 比較例10 | 比較例11 | |
E1 | 100 | 100 | 40 | 100 | 100 | 40 |
E4 | 60 | 60 | ||||
P1 | 53 | 53 | 20 | |||
P4 | 35 | 35 | 20 | |||
P5 | 18 | 18 | ||||
P7 | 19 | 19 | ||||
P8 | 1.0 | 1.0 | ||||
B1 | 50 | 50 | ||||
C1 | 0.12 | 0.15 | 0.09 | 0.10 | ||
C3 | 0.20 | 0.15 | ||||
銅箔剝離強度 (kN/m) | 1.4 | 1.5 | 1.6 | 1.4 | 1.6 | 1.4 |
層間接著力 (kN/m) | 1.1 | 1.2 | 1.0 | 1.1 | 1.2 | 0.8 |
相對介電常數 | 3.03 | 3.01 | 3.05 | 3.13 | 3.13 | 3.15 |
介電損耗正切 | 0.018 | 0.017 | 0.011 | 0.021 | 0.020 | 0.015 |
Tg(℃) | 182 | 176 | 157 | 186 | 180 | 160 |
實施例12及比較例12~比較例13
以表4的調配量(份)調配,進行與實施例1同樣的操作,獲得積層板及試驗片。將積層板的阻燃性、銅箔剝離強度、層間接著力及Tg的測定結果、以及試驗片的相對介電常數及介電損耗正切的測定結果示於表4中。
[表4]
實施例12 | 比較例12 | 比較例13 | |
E7 | 100 | 100 | 100 |
P1 | 94 | ||
P7 | 33 | ||
P8 | 3.3 | ||
C1 | 0.10 | 0.05 | |
銅箔剝離強度(kN/m) | 1.8 | 1.7 | 1.5 |
層間接著力(kN/m) | 1.4 | 1.3 | 1.0 |
阻燃性 | V-0 | V-1 | V-0 |
相對介電常數 | 2.96 | 3.38 | 3.31 |
介電損耗正切 | 0.015 | 0.023 | 0.018 |
Tg(℃) | 139 | 137 | 169 |
實施例13
為了進行作為注塑樹脂的評價,混煉作為環氧樹脂的100份的E8、作為硬化劑的109份的P1、以及作為硬化促進劑的1.0份的C2、作為填料的65份的F1,獲得樹脂組成物。使用所獲得的環氧樹脂組成物於175℃下成形,進而於175℃下進行12小時的後固化,獲得硬化物。將硬化物的相對介電常數、介電損耗正切及Tg的測定結果示於表5中。
實施例14~實施例15及比較例14~比較例16
以表5的調配量(份)調配,進行與實施例13同樣的操作,獲得硬化物。將進行與實施例13同樣的試驗而得的結果示於表5中。
[表5]
實施例13 | 實施例14 | 實施例15 | 比較例14 | 比較例15 | 比較例16 | |
E8 | 100 | 100 | ||||
E9 | 100 | 100 | ||||
E10 | 100 | 100 | ||||
P1 | 109 | 120 | 170 | |||
P7 | 38 | 42 | 60 | |||
C2 | 1.0 | 1.0 | 1.0 | 1.0 | 1.0 | 1.0 |
F1 | 65 | 70 | 80 | 45 | 45 | 50 |
相對介電常數 | 2.50 | 2.43 | 2.57 | 2.79 | 2.67 | 2.82 |
介電損耗正切 | 0.012 | 0.012 | 0.014 | 0.019 | 0.018 | 0.020 |
Tg(℃) | 148 | 146 | 156 | 149 | 147 | 158 |
如由該些結果可知般,通式(1)所表示的多元羥基樹脂,即含二環戊烯基的2,6-二取代-二環戊二烯型酚樹脂及含有該些的樹脂組成物能夠提供顯現出非常良好的低介電特性、進而接著力亦優異的樹脂硬化物。
[產業上之可利用性]
本發明的環氧樹脂組成物可用於積層、成型、接著等各種用途中,作為高速通訊設備的電子材料有用,尤其可較佳地用於強烈要求低介電損耗正切的行動用途或伺服器用途等中。
a:通式(1)的n=1體與通式(1)的不存在R2
加成體的n=1體的混合體
b:通式(1)的n=0體
c:由二環戊二烯骨架的烯烴部位的C-H伸縮振動引起的波峰
d:由苯酚核的C-O伸縮振動引起的吸收
圖1是合成例1中得到的多元羥基樹脂的凝膠滲透層析(gel permeation chromatography,GPC)圖。
圖2是合成例1中得到的多元羥基樹脂的紅外(Infrared,IR)圖。
a:通式(1)的n=1體與通式(1)的不存在R2
加成體的n=1
體的混合體
b:通式(1)的n=0體
Claims (7)
- 如請求項1所述的環氧樹脂組成物,其中多元羥基樹脂的羥基當量為190 g/eq.~500 g/eq.。
- 一種硬化物,其是將如請求項1或請求項2所述的環氧樹脂組成物硬化而成。
- 一種密封材,其特徵在於,使用如請求項1或請求項2所述的環氧樹脂組成物。
- 一種電路基板用材料,其特徵在於,使用如請求項1或請求項2所述的環氧樹脂組成物。
- 一種預浸體,其特徵在於,使用如請求項1或請求項2所述的環氧樹脂組成物。
- 一種積層板,其特徵在於,使用如請求項1或請求項2所述的環氧樹脂組成物。
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