TW202244107A - 化合物、混合物、硬化性樹脂組成物及其硬化物 - Google Patents
化合物、混合物、硬化性樹脂組成物及其硬化物 Download PDFInfo
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- TW202244107A TW202244107A TW111107557A TW111107557A TW202244107A TW 202244107 A TW202244107 A TW 202244107A TW 111107557 A TW111107557 A TW 111107557A TW 111107557 A TW111107557 A TW 111107557A TW 202244107 A TW202244107 A TW 202244107A
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
- C07C15/50—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals polycyclic non-condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C22/00—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom
- C07C22/02—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom having unsaturation in the rings
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Abstract
Description
本發明係關於化合物、混合物、硬化性樹脂組成物及其硬化物,並且適合使用在半導體密封材、印刷配線基板、增層積層板等電氣及電子零件;碳纖維強化塑膠、玻璃纖維強化塑膠等輕量高強度材料;3D列印用途。
近年來,裝載電氣及電子零件之積層板由於其應用領域的擴大,使得要求特性變得廣泛且高度化。以往的半導體晶片是以裝載於金屬製的引線架者為主流,惟中央處理裝置(以下表示為CPU)等處理能力高的半導體晶片被裝載於以高分子材料所製作之積層板之情形乃逐漸增多。
尤其在智慧型手機等所使用之半導體封裝(以下表示為PKG)中,為了因應小型化、薄型化及高密度化的要求而要求PKG基板的薄型化,惟PKG基板變薄時剛性會降低,所以會因為將PKG焊接安裝於主機板(PCB)時之加熱而導致較大翹曲的產生等缺失。為了降低此情況,係要求高Tg的PKG基板材料。
除此之外,於目前正加速開發之第5代通訊系統「5G」中,可預見更進一步之大容量化與高速通訊的進展。於5G中,所使用之頻率的高頻化進
展迅速,對於實現應用了高頻之高速通訊而言,係要求基板材料之更進一步的性能提升。例如為了降低傳輸損耗,具有低介電特性者等乃為重要,且要求介電正切在至少10GHz時須為0.005以下。於印刷基板上所產生之傳輸損耗係來自導體損耗與電介質損耗(非專利文獻1)。導體損耗係肇因於基板上之配線等導體的電阻成分,可分為因高頻下的表層效應所造成之損耗以及因銅箔表面的粗糙度所造成之散射損耗。由於愈是高頻,電訊號愈在銅箔表面附近流通(以從銅箔表面之距離計,1GHz:2.1μm、10GHz:0.66μm),為了降低表層效應,近年來已積極進行銅箔的低粗度化。從該情況來看,對樹脂材料的要求之一係逐漸以確保相對於低粗度銅箔之密著性者為課題,低介電材料如以PTFE(聚四氟乙烯)和LCP(液晶聚合物)為代表般,乃缺乏密著性,且此等材料為熱塑性材料,所以亦缺乏成形性。有鑑於此,係期待開發出一種密著性及低介電特性、成形性優異之熱硬化性樹脂。
再者,於汽車領域中電子化進展迅速,於引擎驅動部附近亦有配置精密電子機器之情形,因而要求更高水準之耐熱及耐濕性。於電車或空調等中已開始使用SiC半導體,由於半導體元件的密封材要求極高的耐熱性,所以以往的環氧樹脂密封材變得無法因應於此要求。
鑑於此情況,係探討可同時滿足耐熱性與低介電正切特性之高分子材料。例如於專利文獻1中,係提出一種含有順丁烯二醯亞胺樹脂以及含丙烯基酚樹脂之組成物。然而,由於殘存有硬化反應時未參與反應之酚性羥基,所以電特性並非充足。此外,於專利文獻2中,係揭示一種以烯丙基來取代羥基之烯丙醚樹脂。然而,其係表示出在190℃時引發克來森重排(Claisen Rearrangement),
且在一般的基板成型溫度之200℃時生成未參與硬化反應之酚性羥基,所以無法滿足電特性。
此外,近年來3D列印係作為三維造型的手法而受到矚目,於航太、汽車以及使用在彼等之電子零件的連接器之要求可靠度的領域中,已開始應用此3D列印的手法。尤其是光硬化系、熱硬化系的樹脂,係已積極探討在以立體光刻造型(SLA:Stereolithography)或數位光處理(DLP:Digital Light Processing)為代表之用途中的應用。因此,於以往從模具中轉印之方式中,主要是要求形狀的穩定性、正確性,而在3D列印用途中,則是要求耐熱性、機械特性、強韌性、阻燃性以及電特性之各種特性,並已積極進行該材料的開發。此外,使用在結構構件時,因吸濕等所導致之特性變化乃成為一項課題。目前在此用途中已應用丙烯酸酯樹脂和環氧樹脂,惟於其硬化物中皆含有多數的酯鍵、醚鍵以及羥基,因此於吸濕上的特性並不足。
[先前技術文獻]
[專利文獻]
專利文獻1:日本國特開平04-359911號公報
專利文獻2:國際公開第2016/002704號
[非專利文獻]
非專利文獻1:印刷基板上高速訊號傳輸中的訊號損耗因素(三井金屬礦業股份有限公司)第29次電子安裝學會春季公演大會16P1-17
本發明係鑑於該狀況而研創者,其目的在於提供一種顯現出優異的耐熱性、電特性、密著性且具有良好的硬化性之化合物、混合物、硬化性樹脂組成物及其硬化物。
亦即,本發明係關於下述[1]至[11]。
[1]
一種化合物,係以下述式(1)所表示,
式(1)中,X表示任意的有機基;X具有複數個時,複數個X可互為相同或不同;A表示亞甲基或氧原子,Q表示碳數1至10的烴基、或鹵烷基;複數個Q可互為相同或不同;R表示碳數1至10的烴基、或鹵烷基;R具有複數個時,複數個R可互為相同或不同;l、m分別表示0至3的整數,n為重複單元且1≦n≦20,p為重複單元且1≦p≦20。
[2]
如前項[1]所述之化合物,其中於前述式(1)中,n為1.1≦n≦20。
[3]
如前項[1]或[2]所述之化合物,其中於前述式(1)中,X為下述式(2)中所記載之(a)至(h)中之任1種以上,
*表示鍵結位置。
[4]
如前項[3]所述之化合物,其中於前述式(1)中,X為前述式(2)中所記載之(a)。[5]一種混合物,係含有如前項[1]至[4]中任一項所述之化合物以及下述式(4-a)所表示之化合物,
式(4-a)中,s為重複單元且1≦s≦20。
[6]
一種硬化性樹脂組成物,係含有如前項[1]至[4]中任一項所述之化合物或是如前項[5]所述之混合物。
[7]
如前項[6]所述之硬化性樹脂組成物,其更含有選自由聚苯醚、聚丁二烯及其變性物所組成之群組中的1種以上。
[8]
如前項[7]所述之硬化性樹脂組成物,其中前述聚丁二烯及其變性物係含有選自由苯乙烯/丁二烯共聚物及丁二烯系熱塑性彈性體所組成之群組中的1種以上。
[9]
一種硬化物,係將如前項[1]至[4]中任一項所述之化合物、如前項[5]所述之混合物或是如前項[6]至[8]中任一項所述之硬化性樹脂組成物進行硬化而得。
[10]一種化合物,係以下述式(3)所表示,
式(3)中,X表示任意的有機基;X具有複數個時,複數個X可互為相同或不同;Z表示鹵素元素;複數個Z可互為相同或不同;A表示亞甲基或氧原子,Q表示碳數1至10的烴基、或鹵烷基;複數個Q可互為相同或不同;R表示碳數1至10的烴基、或鹵烷基;R具有複數個時,複數個R可互為相同
或不同;l、m分別表示0至3的整數,n為重複單元且1≦n≦20,p為重複單元且1≦p≦20。
[11]
一種如前項[1]至[4]中任一項所述之化合物的製造方法,係包含:在鹼性觸媒的存在下,將如前項[10]所述之前述式(3)所表示之化合物進行脫鹵氫反應之步驟。
本發明之化合物的硬化性優異,且其硬化物具有高耐熱性、低介電特性、密著性優異之特性。因此為有用於電氣及電子零件的密封或電路基板、碳纖維複合材等之材料。
此外,由於本發明之化合物的反應性優異,所以單獨地硬化亦為其較佳樣態之一。
圖1顯示實施例1之GPC圖。
圖2顯示實施例1之1H-NMR圖。
圖3顯示實施例2之GPC圖。
圖4顯示實施例2之1H-NMR圖。
圖5顯示實施例3之GPC圖。
圖6顯示實施例3之1H-NMR圖。
圖7顯示實施例4之GPC圖。
圖8顯示實施例4之1H-NMR圖。
圖9顯示參考例1之GPC圖。
圖10顯示參考例1之1H-NMR圖。
圖11顯示參考例2之GPC圖。
圖12顯示參考例2之1H-NMR圖。
本發明之化合物係以下述式(1)所表示。
式(1)中,X表示任意的有機基。X具有複數個時,複數個X可互為相同或不同。A表示亞甲基或氧原子,Q表示碳數1至10的烴基、或鹵烷基。複數個Q可互為相同或不同。R表示碳數1至10的烴基、或鹵烷基。R具有複數個時,複數個R可互為相同或不同。l、m分別表示0至3的整數,n為重複單元且1≦n≦20,p為重複單元且1≦p≦20。
前述式(1)中,m通常為0至3的整數,較佳為0至2的整數,更佳為0。n通常為1≦n≦20,較佳為1.1≦n≦20,更佳為1.1≦n≦10,特佳為1.1≦n≦5。n之值可從藉由烯烴化合物之凝膠滲透層析法(GPC:Gel Permeation Chromatography)的測定所求取之重量平均分子量(Mw)之值來算出。重量平均分
子量較佳為200以上且未達5000,更佳為300以上且未達3000,特佳為400以上且未達2000。重量平均分子量未達5000時,容易藉由水洗來進行精製,為200以上時,於溶劑餾除步驟中,目的化合物揮發之風險少。
p通常為1≦p≦20,較佳為1≦p≦5,更佳為1≦p≦3,特佳為1≦p≦2。
R通常為碳數1至10的烴基,較佳為碳數1至5,更佳為碳數1至3。R為碳數3以下之烴在暴露於高頻時不易產生分子振動,所以電特性優異。
前述式(1)中,Q通常為碳數1至10的烴基,較佳為碳數1至5,更佳為碳數1至3。碳數3以下之烴在暴露於高頻時不易產生分子振動,所以電特性優異。
前述式(1)中,l通常為0至3,較佳為0至2,更佳為0。l為0時,從分子的對稱性之觀點來看可謂特佳。具有對稱性高的分子結構時,硬化物亦同樣容易得到對稱性高之硬化物的化學鍵結樣式。作為化學鍵結樣式的對稱性高之硬化物係不易產生分子振動,具有抵銷偶極之效果,所以介電特性等為優異。此外,將如二苯基甲烷之分子內具有2個以上芳香環之化合物導入分子內者,係顯現出降低官能基密度並降低硬化收縮之效果。硬化收縮愈小,對銅箔等之密著性亦容易提升。
此外,於前述式(1)中,X較佳為下述式(2)中所記載之(a)至(h)中任1種以上,更佳為(a)至(c)及(e)至(h)中任1種以上,特佳為(a)。此係由於芳香環的共軛增大時,偶極矩變大,而唯恐導致介電特性的惡化之故。
*表示鍵結位置。
本發明之前述式(1)所表示之化合物係由下述式(3)所表示之化合物所衍生。
式(3)中,X表示任意的有機基。X具有複數個時,複數個X可互為相同或不同。Z表示鹵素元素。複數個Z可互為相同或不同。A表示亞甲基或氧原子,Q表示碳數1至10的烴基、或鹵烷基。複數個Q可互為相同或不同。R表示碳數1至10的烴基、或鹵烷基。R具有複數個時,複數個R可互為相同或不同。l、m分別表示0至3的整數,n為重複單元且1≦n≦20,p為重複單元且1≦p≦20。
前述式(3)的X、l、m、n、p、A、Q、R的較佳範圍係與前述式(1)相同。此外,Z較佳為溴原子或氯原子,特佳為溴原子。
本發明之前述式(1)所表示之化合物係由前述式(3)所表示之化合物所衍生。具體而言,可藉由在鹼性觸媒的存在下,於溶劑中將前述式(3)所表示之化合物進行脫鹵氫反應之方法而製得。此外,為了提升脫鹵氫反應的反應率,可重複進行複數次下列操作:從施以脫鹵氫反應後之溶液中藉由水洗來去除鹽,然後送回反應容器並再次施以脫鹵氫反應。殘存於所得到之烯烴樹脂之鹵素量較佳為10至10000ppm,更佳為10至1000ppm,又更佳為10至900ppm。脫鹵氫反應不足時,殘存的鹵乙烷有時會導致電特性的惡化。所使用之溶劑可列舉例如:甲苯、二甲苯等芳香族溶劑;環己烷、正己烷等脂肪族溶劑;二乙醚、二異丙醚等醚類;乙酸乙酯、乙酸丁酯等酯系溶劑;甲基異丁酮、環戊酮、丙酮等酮系溶劑等非水溶性溶劑,惟並不限定於此等,亦可併用2種以上。此外,除了前述非水溶性溶劑之外,亦可併用非質子性極性溶劑。可列舉例如:二甲基碸、二甲基亞碸、二甲基甲醯胺、二甲基乙醯胺、1,3-二甲基-2-咪唑啶酮(1,3-dimethyl-2-imidazolidinone)、N-甲基吡咯啶酮等,亦可併用2種以上。觸媒並無特別限定,可列舉氫氧化鈉、氫氧化鉀、碳酸鉀等鹼性觸媒。
前述式(3)所表示之化合物的製法並無特別限定,例如可在鹽酸或磺酸、活性白土等酸觸媒下,將具有2-溴乙基苯結構之化合物、與雙鹵甲基芳基化合物、與二苯基甲烷系化合物或二苯基醚系化合物進行反應;或是在鹽酸或磺酸、活性白土等酸觸媒下,將具有2-溴乙基苯結構之化合物、與雙羥基甲基芳基化合物、與二苯基甲烷系化合物或二苯基醚系化合物進行反應。在將鹽酸使用作為觸媒時,係以氫氧化鈉或氫氧化鉀等鹼金屬進行中和,並在以甲苯或二甲苯等
芳香族烴溶劑進行萃取後,進行水洗直到排水成為中性為止,然後使用蒸餾器等來餾除溶劑,藉此可得到目的之分子內具有至少2個以上的2-溴乙基苯結構之化合物。將此時之原料饋入比率的較佳範圍呈示如下。雙鹵甲基芳基化合物(或是雙羥基甲基芳基化合物)相對於具有2-溴乙基苯結構之化合物1莫耳之饋入比率較佳為0.1至0.95莫耳,更佳為0.2至0.9莫耳,特佳為0.25至0.8莫耳。此外,此時,二苯基甲烷系化合物或二苯基系化合物相對於雙鹵甲基芳基化合物(或是雙羥基甲基芳基化合物)1莫耳之饋入比率較佳為0.1至0.95莫耳,更佳為0.2至0.9莫耳,特佳為0.25至0.8莫耳。若位於上述範圍內,則不會有殘存原料並且可顯現二苯基甲烷結構或二苯基結構的導入效果。
具有2-溴乙基苯結構之化合物可列舉:2-溴乙基苯、1-(2-溴乙基)-2-甲基苯、1-(2-溴乙基)-3-甲基苯、1-(2-溴乙基)-4-甲基苯、1-(2-溴乙基)-2,3-二甲基苯、1-(2-溴乙基)-2,4-二甲基苯、1-(2-溴乙基)-2,5-二甲基苯、1-(2-溴乙基)-2,6-二甲基苯等,惟並不限定於此等。於碳數較多時,溶劑溶解性提升但耐熱性會降低,故較佳為無取代或經碳數1至3的烷基所取代,更佳為無取代或經碳數1至2的烷基所取代,最佳為無取代或經甲基所取代。
雙鹵甲基芳基化合物可列舉:二氟鄰二甲苯、二氟間二甲苯、二氟對二甲苯、二氯鄰二甲苯、二氯間二甲苯、二氯對二甲苯、二溴鄰二甲苯、二溴間二甲苯、二溴對二甲苯、二碘鄰二甲苯、二碘間二甲苯、二碘對二甲苯、4,4'-雙氟亞甲基聯苯、4,4'-雙氯亞甲基聯苯、4,4'-雙溴亞甲基聯苯、4,4'-雙碘亞甲基聯苯、2,4-雙氟亞甲基聯苯、2,4-雙氯亞甲基聯苯、2,4-雙溴亞甲基聯苯、2,4-雙碘亞甲基聯苯、2,2'-雙氟亞甲基聯苯、2,2'-雙氯亞甲基聯苯、2,2'-雙溴亞甲基聯苯、2,2'-雙碘亞甲基聯苯,從合成時之原料的反應性之觀點來看,較佳為氯化物
系化合物、溴化物系化合物、碘化系化合物,更佳可列舉氯化物系化合物、溴化物系化合物。此外,其他任意的鹵化合物可列舉:三聚氟氰、三聚氯氰、三聚溴氰、三聚碘氰等,惟並不限定於此。
雙羥基甲基芳基化合物可列舉:鄰苯二甲醇、間苯二甲醇、對苯二甲醇、4,4'-雙羥基甲基聯苯、2,4-雙羥基甲基聯苯、2,2'-雙羥基甲基聯苯、α,α,α',α'-四甲基-1,4-苯二甲醇、α,α,α',α'-四甲基-1,3-苯二甲醇、α,α,α',α'-四甲基-1,2-苯二甲醇等,惟並不限定於此。此等可單獨使用或併用2種以上。
於具有2-溴乙基苯結構之化合物與鹵甲基芳基化合物等之反應時,可視需要除了鹽酸、磷酸、硫酸、甲酸、對甲苯磺酸、甲烷磺酸之外,可使用氯化鋁、氯化鋅等路易斯酸;活性白土、酸性白土、白碳、沸石、二氧化矽氧化鋁等固體酸;酸性離子交換樹脂等來作為觸媒。此等可單獨使用或併用兩種以上。相對於所使用之具有2-溴乙基苯結構之化合物1莫耳,觸媒的用量通常為0.1至0.8莫耳,較佳為0.2至0.7莫耳。觸媒的用量過多時,反應溶液的黏度過高,會有難以攪拌之虞,過少時,反應的進行有變慢之虞。反應可視需要來選擇使用己烷、環己烷、辛烷、甲苯、二甲苯等有機溶劑來進行,亦可在無溶劑下進行。例如在將酸性觸媒添加於具有2-溴乙基苯結構之化合物、鹵甲基芳基化合物及溶劑之混合溶液後,於觸媒含有水時係藉由共沸將水從系統內排除。然後於40至180℃,較佳於50至170℃進行0.5至20小時的反應。反應結束後,以鹼性水溶液將酸性觸媒進行中和後,將非水溶性有機溶劑加入油層並重複進行水洗直至廢水成為中性為止。
前述式(3)所表示之化合物的軟化點較佳為80℃以下,更佳為70℃以下。軟化點為80℃以下時,形成為烯烴樹脂時之黏度變低,容易含浸於碳
纖維或玻璃纖維。增加稀釋溶劑來降低黏度時,於含浸步驟中樹脂可能會無法充分地附著於纖維狀材料。
本發明之混合物係含有前述式(1)所表示之化合物以及下述式(4)所表示之化合物。
式(4)中,s為重複單元且1≦s≦20。X、R、m與前述式(1)中所示者為相同。
於本發明之混合物中,於前述式(4)所表示之化合物中,特佳係含有下述式(4-a)所表示之化合物。
式(4-a)中,s為重複單元且1≦s≦20。
如上述般,前述式(1)所表示之化合物是由前述式(3)所表示之化合物所衍生,於製造前述式(3)所表示之化合物時,若不加入單離步驟,則前述式(3)所表示之化合物係含有一定量之下述式(5)所表示之化合物來製造。
式(5)中,X、R、m、Z與前述式(3)中所示者為相同。s為重複單元且1≦s≦20。
因此,藉由將前述式(3)所表示之化合物以及前述式(5)所表示之化合物的混合物作為起始原料,來製造含有前述式(1)所表示之化合物以及前述式(4)所表示之化合物之本發明的混合物。
於本發明之混合物中,前述式(1)所表示之化合物與前述式(4)所表示之化合物的含有比率可使用GPC(檢測器:RI)來規定,並且從前述式(1)及(4)所表示之化合物的單核體峰值比率來計算。所謂前述式(1)所表示之化合物的單核體,為前述式(1)中的p及n為1之成分,所謂前述式(4)所表示之化合物的單核體,為前述式(4)中的p及s為1之成分。將前述式(1)所表示之化合物之單核體的含量設為α,將前述式(4)所表示之化合物之單核體的含量設為β時,α/β較佳為0.1至2.0,更佳為0.2至1.5,又更佳為0.3至1.0。若位於此範圍內,則本發明之混合物可在不顯著損及耐熱性下提升密著性。
含有本發明之化合物或混合物之組成物係含有聚合抑制劑。可使用的聚合抑制劑可列舉:酚系、硫系、磷系、受阻胺系、亞硝基(Nitroso)系、氮氧自由基(Nitroxyl Radical)系等聚合抑制劑。聚合抑制劑可在合成前述式(1)所表示之化合物時添加,或是於合成後添加。此外,聚合抑制劑可單獨使用或組合2種以上而使用。相對於樹脂成分100重量份,聚合抑制劑的用量通常為0.008至
1重量份,較佳為0.01至0.5重量份。此等聚合抑制劑可分別單獨使用,亦可組合2種以上而併用。於本發明中,較佳為酚系、受阻胺系、亞硝基系、氮氧自由基系。當中,氮氧自由基系的保存穩定性優異,故特佳。
酚系聚合抑制劑的具體例可例示:2,6-二(第三丁基)對甲酚、丁基化羥基甲氧苯、2,6-二(第三丁基)對乙酚、硬脂基-β-(3,5-二(第三丁基)-4-羥基苯基)丙酸酯、異辛基-3-(3,5-二(第三丁基)-4-羥基苯基)丙酸酯、2,4-雙-(正辛基硫基)-6-(4-羥基-3,5-二(第三丁基)苯胺基)-1,3,5-三嗪、2,4-雙[(辛基硫基)甲基]鄰甲酚等單酚類;2,2'-亞甲基雙(4-甲基-6-第三丁基酚)、2,2'-亞甲基雙(4-乙基-6-第三丁基酚)、4,4'-硫雙(3-甲基-6-第三丁基酚)、4,4'-亞丁基雙(3-甲基-6-第三丁基酚)、三乙二醇-雙[3-(3-第三丁基-5-甲基-4-羥基苯基)丙酸酯]、1,6-己烷二醇-雙[3-(3,5-二(第三丁基)-4-羥基苯基)丙酸酯]、N,N'-六亞甲基雙(3,5-二(第三丁基)-4-羥基-氫桂皮醯胺)、2,2-硫基-二伸乙基雙[3-(3,5-二(第三丁基)-4-羥基苯基)丙酸酯]、3,5-二(第三丁基)-4-羥基苄基膦酸酯-二乙酯、3,9-雙[1,1-二甲基-2-{β-(3-第三丁基-4-羥基-5-甲基苯基)丙醯氧基}乙基]2,4,8,10-四氧雜螺環[5,5]十一烷、雙(3,5-二(第三丁基)-4-羥基苄基磺酸乙基)鈣等雙酚類;1,1,3-三(2-甲基-4-羥基-5-第三丁基苯基)丁烷、1,3,5-三甲基-2,4,6-三(3,5-二(第三丁基)-4-羥基苄基)苯、四-[亞甲基-3-(3',5'-二(第三丁基)-4'-羥基苯基)丙酸酯]甲烷、雙[3,3'-雙-(4'-羥基-3'-第三丁基苯基)丁酸]二醇酯、三-(3,5-二(第三丁基)-4-羥基苄基)-異三聚氰酸酯、1,3,5-三(3',5'-二(第三丁基)-4'-羥基苄基)-均三嗪-2,4,6-(1H,3H,5H)三酮、生育酚等高分子型酚類。
硫系聚合抑制劑的具體例可例示:二月桂基-3,3'-硫二丙酸酯、二肉荳蔻基-3,3'-硫二丙酸酯、二硬脂基-3,3'-硫二丙酸酯等。
磷系聚合抑制劑的具體例可例示:亞磷酸三苯酯、亞磷酸二苯基異癸酯、亞磷酸苯基二異癸酯、亞磷酸三(壬基苯基)酯、亞磷酸二異癸基新戊四醇酯、亞磷酸三(2,4-二(第三丁基)苯基)酯、亞磷酸環狀新戊烷四基雙(十八基)酯、亞磷酸環狀新戊烷四基雙(2,4-二(第三丁基)苯基)酯、亞磷酸環狀新戊烷四基雙(2,4-二(第三丁基)-4-甲基苯基酯、亞磷酸雙[2-第三丁基-6-甲基-4-{2-(十八烷基氧基羰基)乙基}苯基]氫酯等亞磷酸酯類;9,10-二氫-9-氧雜-10-磷雜菲-10-氧化物、10-(3,5-二(第三丁基)-4-羥基苄基)-9,10-二氫-9-氧雜-10-磷雜菲-10-氧化物、10-癸氧基-9,10-二氫-9-氧雜-10-磷雜菲-10-氧化物等氧雜磷雜菲氧化物類等。
受阻胺系聚合抑制劑的具體例可例示:Adekastab LA-40MP、Adekastab LA-40Si、Adekastab LA-402AF、Adekastab LA-87、Adekastab LA-82、Adekastab LA-81、Adekastab LA-77Y、Adekastab LA-77G、Adekastab LA-72、Adekastab LA-68、Adekastab LA-63P、Adekastab LA-57、Adekastab LA-52、Chimassorb 2020FDL、Chimassorb 944FDL、Chimassorb 944LD、Tinuvin 622SF、Tinuvin PA144、Tinuvin 765、Tinuvin 770DF、Tinuvin XT55FB、Tinuvin 111FDL、Tinuvin 783FDL、Tinuvin 791FB等,惟並不限定於此。
亞硝基系聚合抑制劑的具體例可列舉:對亞硝基酚、N-亞硝基二苯基胺、N-亞硝基苯基羥基胺的銨鹽(Cupferron)等,較佳為N-亞硝基苯基羥基胺的銨鹽(Cupferron)。
氮氧自由基系聚合抑制劑的具體例可列舉:二(第三丁基)硝基氧化物、2,2,6,6-四甲基哌啶-1-氧基(2,2,6,6-tetramethylpiperidine-1-oxyl)、4-羥基-2,2,6,6-四甲基哌啶-1-氧基、4-側氧基-2,2,6,6-四甲基哌啶-1-氧基、4-胺基-2,2,6,6-
四甲基哌啶-1-氧基、4-甲氧基-2,2,6,6-四甲基哌啶-1-氧基、4-乙醯氧基-2,2,6,6-四甲基哌啶-1-氧基、4-苄醯氧基-2,2,6,6-四甲基哌啶-1-氧基等,惟並不限定於此等。
本發明之硬化性樹脂組成物可使用一般所知的任意材料來作為本發明之化合物或混合物以外的硬化性樹脂。具體上可列舉:酚樹脂、環氧樹脂、胺樹脂、含活性烯烴樹脂、異氰酸酯樹脂、聚醯胺樹脂、聚醯亞胺樹脂、氰酸酯樹脂、丙烯基樹脂、甲基烯丙基樹脂、活性酯樹脂等,可使用1種或併用複數種。此外,從耐熱性、密著性、介電特性之均衡來看,較佳係含有環氧樹脂、含活性烯烴樹脂、氰酸酯樹脂。藉由含有此等硬化性樹脂,可改善硬化物的脆度以及提升與金屬之密著性,於回焊時或冷熱循環等可靠度試驗中,可抑制封裝的龜裂。
相對於前述式(1)所表示之化合物,上述硬化性樹脂的用量較佳為10質量倍以下,更佳為5質量倍以下,特佳為3質量倍以下之質量範圍。此外,較佳的下限值為0.5質量倍以上,更佳為1質量倍以上。若為10質量倍以下,則可活用前述式(1)所表示之化合物之耐熱性或介電特性的效果。
酚樹脂、環氧樹脂、胺樹脂、含活性烯烴樹脂、異氰酸酯樹脂、聚醯胺樹脂、聚醯亞胺樹脂、氰酸酯樹脂、活性酯樹脂,可使用下列所例示者。
酚樹脂:酚類(酚、烷基取代酚、芳香族取代酚、氫醌(Hydroquinone)、間苯二酚(Resorcin)、萘酚(Naphthol)、烷基取代萘酚、二羥基苯、烷基取代二羥基苯、二羥基萘等)與各種醛(甲醛、乙醛、烷醛、苯甲醛、烷基取代苯甲醛、羥基苯甲醛、萘醛、戊二醛、鄰苯二甲醛、巴豆醛(Crotonaldehyde)、桂皮醛(Cinnamaldehyde)、呋喃甲醛(Furfural)等)之縮聚物;酚類與各種二烯化合物(二環戊二烯、萜類(Terpene)、乙烯環己烯、降莰二烯、乙烯降莰烯、四氫茚
(Tetrahydroindene)、二乙烯苯、二乙烯聯苯、二異丙烯聯苯、丁二烯、異戊二烯等)之聚合物;酚類與酮類(丙酮、丁酮、甲基異丁酮、苯乙酮、二苯基酮等)之縮聚物;藉由酚類與取代聯苯類(4,4'-雙(氯甲基)-1,1'-聯苯及4,4'-雙(甲氧基甲基)-1,1'-聯苯等)或取代苯基類(1,4-雙(氯甲基)苯、1,4-雙(甲氧基甲基)苯及1,4-雙(羥基甲基)苯等)等之縮聚所得到之酚樹脂;雙酚類與各種醛之縮聚物;聚苯醚。
環氧樹脂:將前述酚樹脂、醇類等進行縮水甘油化之縮水甘油醚系環氧樹脂;以4-乙烯基-1-環己烯二環氧化物或3,4-環氧基環己基甲基-3,4'-環氧基環己烷羧酸酯等為代表之脂環式環氧樹脂;以四縮水甘油二胺基二苯基甲烷(TGDDM)或三縮水甘油基對胺基酚等為代表之縮水甘油胺系環氧樹脂;縮水甘油酯系環氧樹脂。
胺樹脂:二胺基二苯基甲烷、二胺基二苯基碸、異佛爾酮二胺、萘二胺、苯胺酚醛清漆、鄰乙基苯胺酚醛清漆、藉由苯胺與氯化二甲苯之反應所得到之苯胺樹脂、日本國特許第6429862號公報所記載之苯胺與取代聯苯類(4,4'-雙(氯甲基)-1,1'-聯苯及4,4'-雙(甲氧基甲基)-1,1'-聯苯等)或取代苯基類(1,4-雙(氯甲基)苯、1,4-雙(甲氧基甲基)苯及1,4-雙(羥基甲基)苯等)。
含活性烯烴樹脂:前述酚樹脂與含活性烯烴的鹵素系化合物(氯甲基苯乙烯、烯丙基氯、甲基烯丙基氯、丙烯醯氯、烯丙基氯等)之縮聚物;含活性烯烴酚類(2-烯丙基酚、2-丙烯基酚、4-烯丙基酚、4-丙烯基酚、丁香酚(Eugenol)、異丁香酚等)與鹵素系化合物(4,4'-雙(甲氧基甲基)-1,1'-聯苯、1,4-雙(氯甲基)苯、4,4'-二氟二苯基酮、4,4'-二氯二苯基酮、4,4'-二溴二苯基酮、三聚氯化氰等)之縮聚物;環氧樹脂或醇類與取代或非取代的丙烯酸酯類(丙烯酸酯、甲基丙烯酸酯等)之縮聚物;順丁烯二醯亞胺樹脂(4,4'-二苯基甲烷雙順丁烯二醯亞胺、聚苯基
甲烷順丁烯二醯亞胺、間苯雙順丁烯二醯亞胺、2,2'-雙[4-(4-順丁烯二醯亞胺苯氧基)苯基]丙烷、3,3'-二甲基-5,5'-二乙基-4,4'-二苯基甲烷雙順丁烯二醯亞胺、4-甲基-1,3-伸苯雙順丁烯二醯亞胺、4,4'-二苯基雙順丁烯二醯亞胺、4,4'-二苯基碸雙順丁烯二醯亞胺、1,3-雙(3-順丁烯二醯亞胺苯氧基)苯、1,3-雙(4-順丁烯二醯亞胺苯氧基)苯)。
異氰酸酯樹脂:對苯二異氰酸酯、間苯二異氰酸酯、對二甲苯二異氰酸酯、間二甲苯二異氰酸酯、2,4-甲苯二異氰酸酯、2,6-甲苯二異氰酸酯、4,4'-二苯基甲烷二異氰酸酯、萘二異氰酸酯等芳香族二異氰酸酯類;異佛爾酮二異氰酸酯、六亞甲二異氰酸酯、4,4'-二環己基甲烷二異氰酸酯、氫化二甲苯二異氰酸酯、降莰烯二異氰酸酯、離胺酸二異氰酸酯等脂肪族或脂環結構的二異氰酸酯類;異氰酸酯單體的一種以上之縮二脲(Biuret)體、或是將上述二異氰酸酯化合物進行三聚化之異氰酸酯體等聚異氰酸酯;藉由上述異氰酸酯化合物與多元醇化合物之胺基甲酸乙酯化反應所得到之聚異氰酸酯。
聚醯胺樹脂:以選自胺基酸(6-胺基己酸、11-胺基十一酸、12-胺基十二酸、對胺基甲基苄酸等)、內醯胺(ε-己內醯胺、ω-十一內醯胺、ω-月桂內醯胺)及二胺(乙二胺、丙二胺、丁二胺、戊二胺、己二胺、庚二胺、辛二胺、壬二胺、癸二胺、十一烷二胺、十二烷二胺、十三烷二胺、十四烷二胺、十五烷二胺、十六烷二胺、十七烷二胺、十八烷二胺、十九烷二胺、二十烷二胺、2-甲基-1,5-二胺基戊烷、2-甲基-1,8-二胺基辛烷等脂肪族二胺;環己二胺、雙-(4-胺基環己基)甲烷、雙(3-甲基-4-胺基環己基)甲烷等脂環式二胺;二甲苯二胺等芳香族二胺等與二羧酸(乙二酸、丙二酸、丁二酸、戊二酸、己二酸、辛二酸(Suberic Acid)、壬二酸(Azelaic Acid)、癸二酸(Sebacic Acid)、十一烷二酸、十二烷二酸等脂肪族
二羧酸;對苯二甲酸、間苯二甲酸、2-氯對苯二甲酸、2-甲基對苯二甲酸、5-甲基間苯二甲酸、5-鈉磺酸基間苯二甲酸、六氫對苯二甲酸、六氫間苯二甲酸等芳香族二羧酸;環己烷二羧酸等脂環族二羧酸;此等二羧酸的二烷酯及二氯化物)之混合物的1種以上作為主要原料之聚合物。
聚醯亞胺樹脂:前述二胺與四羧酸二酐(4,4'-(六氟異亞丙基)二鄰苯二甲酸酐、5-(2,5-二側氧基四氫-3-呋喃基)-3-甲基-環己烯-1,2二羧酸酐、焦蜜石酸二酐、1,2,3,4-苯四羧酸二酐、3,3',4,4'-二苯基酮四羧酸二酐、2,2',3,3'-二苯基酮四羧酸二酐、3,3',4,4'-聯苯四羧酸二酐、3,3',4,4'-二苯基碸四羧酸二酐、2,2',3,3'-聯苯四羧酸二酐、亞甲基-4,4'-二鄰苯二甲酸二酐、1,1-亞乙基-4,4'-二鄰苯二甲酸二酐、2,2'-亞丙基-4,4'-二鄰苯二甲酸二酐、1,2-伸乙基-4,4'-二鄰苯二甲酸二酐、1,3-三亞甲基-4,4'-二鄰苯二甲酸二酐、1,4-四亞甲基-4,4'-二鄰苯二甲酸二酐、1,5-五亞甲基-4,4'-二鄰苯二甲酸二酐、4,4'-氧基二鄰苯二甲酸二酐、硫-4,4'-二鄰苯二甲酸二酐、磺醯基-4,4'-二鄰苯二甲酸二酐、1,3-雙(3,4-二羧基苯基)苯二酐、1,3-雙(3,4-二羧基苯氧基)苯二酐、1,4-雙(3,4-二羧基苯氧基)苯二酐、1,3-雙[2-(3,4-二羧基苯基)-2-丙基]苯二酐、1,4-雙[2-(3,4-二羧基苯基)-2-丙基]苯二酐、雙[3-(3,4-二羧基苯氧基)苯基]甲烷二酐、雙[4-(3,4-二羧基苯氧基)苯基]甲烷二酐、2,2-雙[3-(3,4-二羧基苯氧基)苯基]丙烷二酐、2,2-雙[4-(3,4-二羧基苯氧基)苯基]丙烷二酐、雙(3,4-二羧基苯氧基)二甲基矽烷二酐、1,3-雙(3,4-二羧基苯基)-1,1,3,3-四甲基二矽氧烷二酐、2,3,6,7-萘四羧酸二酐、1,4,5,8-萘四羧酸二酐、1,2,5,6-萘四羧酸二酐、3,4,9,10-苝四羧酸二酐、2,3,6,7-蒽四羧酸二酐、1,2,7,8-菲四羧酸二酐、伸乙四羧酸二酐、1,2,3,4-丁烷四羧酸二酐、1,2,3,4-環丁烷四羧酸二酐、環戊烷四羧酸二酐、環己烷-1,2,3,4-四羧酸二酐、環己烷-1,2,4,5-四羧酸二酐、3,3',4,4'-雙環己
基四羧酸二酐、羰基-4,4"-雙(環己烷-1,2-二羧酸)二酐、亞甲基-4,4'-雙(環己烷-1,2-二羧酸)二酐、1,2-伸乙基-4,4'-雙(環己烷-1,2-二羧酸)二酐、1,1-亞乙基-4,4'-雙(環己烷-1,2-二羧酸)二酐、2,2-亞丙基-4,4'-雙(環己烷-1,2-二羧酸)二酐、氧基-4,4'-雙(環己烷-1,2-二羧酸)二酐、硫-4,4'-雙(環己烷-1,2-二羧酸)二酐、磺醯基-4,4'-雙(環己烷-1,2-二羧酸)二酐、雙環[2,2,2]辛-7-烯-2,3,5,6-四羧酸二酐、rel-[1S,5R,6R]-3-氧雜雙環[3,2,1]辛烷-2,4-二酮-6-螺環-3'-(四氫呋喃-2',5'-二酮)、4-(2,5-二側氧基四氫呋喃-3-基)-1,2,3,4-四氫萘-1,2-二羧酸酐、乙二醇-雙-(3,4-二羧酸酐苯基)醚、4,4'-聯苯雙(偏苯三甲酸單酯酸酐)、9,9'-雙(3,4-二羧基苯基)茀二酐)之縮聚物。
氰酸酯樹脂:為藉由將酚樹脂與鹵化氰進行反應所得到之氰酸酯化合物,具體例可列舉:二氰氧苯、三氰氧苯、二氰氧萘、二氰氧聯苯、2,2'-雙(4-氰氧苯基)丙烷、雙(4-氰氧苯基)甲烷、雙(3,5-二甲基-4-氰氧苯基)甲烷、2,2'-雙(3,5-二甲基-4-氰氧苯基)丙烷、2,2'-雙(4-氰氧苯基)乙烷、2,2'-雙(4-氰氧苯基)六氟丙烷、雙(4-氰氧苯基)碸、雙(4-氰氧苯基)硫醚、酚-酚醛清漆氰氧、將酚-二環戊二烯共縮合物的羥基轉化為氰酸酯基者等,惟並不限定於此等。
此外,於日本特開2005-264154號公報中合成方法所記載之氰酸酯化合物,由於低吸濕性、阻燃性、介電特性優異,所以特別適合使用作為氰酸酯化合物。
為了視需要將氰酸酯基進行三聚物化來形成對稱-三嗪環,氰酸酯樹脂可含有環烷酸鋅、環烷酸鈷、環烷酸銅、環烷酸鉛、辛酸鋅、辛酸錫、乙醯丙酮酸鉛、順丁烯二酸二丁基錫等觸媒。相對於硬化性樹脂組成物的合計質量100質量份,觸媒通常以0.0001至0.10質量份,較佳以0.00015至0.0015質量份來使用。
活性酯樹脂:可視需要來使用環氧樹脂等之1分子中具有1個以上的活性酯基之化合物,作為本發明之前述式(1)所表示之化合物以外之硬化性
樹脂的硬化劑。活性酯系硬化劑較佳為酚酯類、硫酚酯類、N-羥基胺酯類、雜環羥基化合物的酯類等之1分子中具有2個以上之反應活性高的酯基之化合物。該活性酯系硬化劑較佳為藉由羧酸化合物及硫代羧酸化合物的至少任一種化合物、與羥基化合物及硫醇化合物的至少任一種化合物之縮合反應而得者。尤其從耐熱性提升之觀點來看,較佳為從羧酸化合物與羥基化合物所得到之活性酯系硬化劑,較佳為從羧酸化合物與酚化合物及萘酚化合物的至少任一種化合物所得到之活性酯系硬化劑。
羧酸化合物可列舉例如:苄酸、乙酸、琥珀酸、順丁烯二酸、伊康酸、鄰苯二甲酸、間苯二甲酸、對苯二甲酸、焦蜜石酸等。
酚化合物或萘酚化合物可列舉例如:氫醌、間苯二酚、雙酚A、雙酚F、雙酚S、酚酞(Phenolphthalein)、甲基化雙酚A、甲基化雙酚F、甲基化雙酚S、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、二羥基二苯基酮、三羥基二苯基酮、四羥基二苯基酮、根皮三酚(Phloroglucin)、苯三醇、二環戊二烯型二酚化合物、酚-酚醛清漆等。在此所謂「二環戊二烯型二酚化合物」,意指酚2分子縮合於二環戊二烯1分子所得到之二酚化合物。
活性酯系硬化劑的較佳具體例可列舉:含有二環戊二烯型二酚結構之活性酯化合物、含有萘結構之活性酯化合物、含有酚-酚醛清漆的乙醯基化物之活性酯化合物、含有酚-酚醛清漆的苄醯基化物之活性酯化合物。當中更佳為含有萘結構之活性酯化合物、含有二環戊二烯型二酚結構之活性酯化合物。所謂「二環戊二烯型二酚結構」,係表示由伸苯基-伸二環戊基-伸苯基所構成之2價結構單元。
活性酯系硬化劑的市售品中,例如含有二環戊二烯型二酚結構之活性酯化合物可列舉:「EXB9451」、「EXB9460」、「EXB9460S」、「HPC-8000-65T」、「HPC-8000H-65TM」、「EXB-8000L-65TM」、「EXB-8150-65T」(DIC公司製);含有萘結構之活性酯化合物可列舉:「EXB9416-70BK」(DIC公司製);含有酚-酚醛清漆的乙醯基化物之活性酯化合物可列舉:「DC808」(三菱化學公司製);含有酚-酚醛清漆的苄醯基化物之活性酯化合物可列舉:「YLH1026」、「YLH1030」、「YLH1048」(三菱化學公司製);作為屬於酚-酚醛清漆的乙醯基化物之活性酯系硬化劑可列舉:「DC808」(三菱化學公司製);含磷原子活性酯系硬化劑可列舉:DIC公司製的「EXB-9050L-62M」等。
本發明之硬化性樹脂組成物亦可併用硬化促進劑(硬化觸媒)來提升硬化性。可使用之硬化促進劑的具體例,較佳係以促進烯烴樹脂或順丁烯二醯亞胺樹脂等可進行自由基聚合之硬化性樹脂的自聚合,或是與其他成分之自由基聚合者為目的來使用自由基聚合起始劑。可使用之自由基聚合起始劑可列舉:過氧化丁酮、過氧化乙醯基丙酮等過氧化酮類;過氧化苄醯等過氧化二醯類;過氧化二異丙苯、1,3-雙-(第三丁基過氧基異丙基)-苯等過氧化二烷類;過氧苯甲酸第三丁酯、1,1-二(第三丁基)過氧基環己烷等過氧基縮酮類;過氧新癸酸α-異丙苯酯、過氧新癸酸第三丁酯、過氧三甲基乙酸第三丁酯、過氧-2-乙基己酸1,1,3,3-四甲基丁酯、過氧-2-乙基己酸第三戊酯、過氧2-乙基己酸第三丁酯、過氧3,5,5-三甲基己酸第三戊酯、過氧3,5,5-三甲基己酸第三丁酯、過氧苯甲酸第三戊酯等過氧酸烷酯類;過氧二碳酸二-2-乙基己酯、過氧二碳酸雙(4-第三丁基環己基)酯、過氧異丙基碳酸第三丁酯、1,6-雙(第三丁基過氧基羰氧基)己烷等過氧碳酸酯類;氫過氧化第三丁基、氫過氧化異丙苯、過氧辛酸第三丁酯、過氧化月桂醯等有機
過氧化物;或是偶氮雙異丁腈、4,4'-偶氮雙(4-氰基戊酸)、2,2'-偶氮雙(2,4-二甲基戊腈)等偶氮系化合物之一般所知的硬化促進劑,惟並不特別限定於此等。較佳為酮過氧化物類、二醯過氧化物類、氫過氧化物類、過氧化二烷基類、過氧基縮酮類、過氧烷酯類、過氧碳酸酯類等,更佳為過氧化二烷基類。相對於硬化性樹脂組成物的100質量份,自由基聚合起始劑的添加量較佳為0.01至5質量份,特佳為0.01至3質量份。所使用之自由基聚合起始劑的量較多時,於聚合反應時分子量不會充分地增加。
此外,亦可視需要來添加或併用自由基聚合起始劑以外的硬化促進劑。可使用之硬化促進劑的具體例可列舉:2-甲基咪唑、2-乙基咪唑及2-乙基-4-甲基咪唑等咪唑類;2-(二甲基胺基甲基)酚或1,8-二氮雜雙環(5,4,0)十一烯-7等三級胺類;三苯基膦等膦類;四丁基銨鹽、三異丙基甲基銨鹽、三甲基癸基銨鹽、鯨蠟基三甲基銨鹽、氫氧化十六基三甲基銨等四級銨鹽;三苯基苄基鏻鹽(Triphenyl Benzyl Phosphonium Salt)、三苯基乙基鏻鹽、四丁基鏻鹽等四級鏻鹽(四級鹽的相對離子有鹵素、有機酸離子、氫氧化物離子等,並無特別指定,特佳為有機酸離子、氫氧化物離子);辛酸錫、羧酸鋅(2-乙基己酸鋅、硬脂酸鋅、蘿酸鋅、肉豆蔻酸鋅)或磷酸酯鋅(辛基磷酸鋅、硬脂基磷酸鋅等)等鋅化合物等的過渡金屬化合物(過渡金屬鹽)等。相對於環氧樹脂100重量份,硬化促進劑的調配量可視需要使用0.01至5.0重量份。
於本發明之硬化性樹脂組成物中,亦可含有含磷化合物作為阻燃性賦予成分。含磷化合物可為反應型者或添加型者。含磷化合物的具體例可列舉:磷酸三甲酯、磷酸三乙酯、磷酸三甲苯酯、磷酸三伸苯二甲酯、磷酸甲苯基二苯酯、磷酸甲苯基-2,6-二伸苯二甲酯、1,3-伸苯雙(磷酸二伸苯二甲酯)、1,4-伸
苯雙(磷酸二伸苯二甲酯)、4,4'-聯苯(磷酸二伸苯二甲酯)等磷酸酯類;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-氧化物等磷烷(Phosphane)類;環氧樹脂與前述磷烷類的活性氫反應所得之含磷環氧化合物、紅磷等,較佳為磷酸酯類、磷烷類或含磷環氧化合物,特佳為1,3-伸苯雙(磷酸二伸苯二甲酯)、1,4-伸苯雙(磷酸二伸苯二甲酯)、4,4'-聯苯(磷酸二伸苯二甲酯)或含磷環氧化合物。含磷化合物的含量較佳係(含磷化合物)/(全環氧樹脂)位於0.1至0.6(重量比)的範圍。0.1以下時,阻燃性不足,0.6以上時,會有對硬化物的吸濕性、介電特性帶來不良影響之虞。
此外,於本發明之硬化性樹脂組成物中,可視需要添加光穩定劑。光穩定劑較適合為受阻胺系的光穩定劑,特佳為HALS等。HALS並無特別限定,具代表性者可列舉:二丁胺.1,3,5-三嗪.N,N'-雙(2,2,6,6-四甲基-4-哌啶基-1,6-己二胺與N-(2,2,6,6-四甲基-4-哌啶基)丁胺之縮聚物;琥珀酸二甲基-1-(2-羥基乙基)-4-羥基-2,2,6,6-四甲基哌啶縮聚物;聚[{6-(1,1,3,3-四甲基丁基)胺基-1,3,5-三嗪-2,4-二基}{(2,2,6,6-四甲基-4-哌啶基)亞胺基}六亞甲{(2,2,6,6-四甲基-4-哌啶基)亞胺基}]、雙(1,2,2,6,6-五甲基-4-哌啶基)[[3,5-雙(1,1-二甲基乙基)-4-羥基苯基]甲基]丁基丙二酸酯、雙(2,2,6,6-四甲基-4-哌啶基)癸二酸酯、雙(1,2,2,6,6-五甲基-4-哌啶基)癸二酸酯、雙(1-辛氧基-2,2,6,6-四甲基-4-哌啶基)癸二酸酯、2-(3,5-二(第三丁基)-4-羥基苄基)-2-正丁基丙二酸雙(1,2,2,6,6-五甲基-4-哌啶基)等。HALS可僅使用1種或是併用2種以上。
再者,於本發明之硬化性樹脂組成物中,亦可視需要來調配黏合劑樹脂。黏合劑樹脂可列舉:縮丁醛系樹脂、縮醛系樹脂、丙烯酸系樹脂、環氧-尼龍系樹脂、NBR-酚系樹脂、環氧-NBR系樹脂、聚醯胺系樹脂、聚醯亞胺系
樹脂、聚矽氧系樹脂等,惟並不限定於此等。黏合劑樹脂的調配量較佳為不損及硬化物的阻燃性、耐熱性之範圍,相對於樹脂成分100質量份,較佳為視需要來使用0.05至50質量份,更佳為0.05至20質量份。
再者,於本發明之硬化性樹脂組成物中,可視需要添加:熔融二氧化矽、結晶二氧化矽、多孔質二氧化矽、氧化鋁、鋯石(Zircon)、矽酸鈣、碳酸鈣、石英粉、碳化矽、氮化矽、氮化硼、氧化鋯、氮化鋁、石墨、鎂橄欖石(Forsterite)、塊滑石(Steatite)、尖晶石(Spinel)、富鋁紅柱石(Mullite)、氧化鈦、滑石、黏土、氧化鐵石棉、玻璃粉末等粉體,或是將此等形成為球形狀或破碎狀之無機填充材。此外,尤其在得到半導體密封用的硬化性樹脂組成物之情形時,上述無機填充材的用量於硬化性樹脂組成物中,通常為80至92質量%,較佳為83至90質量%的範圍。
於本發明之硬化性樹脂組成物中,可視需要調配一般所知的添加劑。可使用之添加劑的具體例可列舉:如聚丁二烯及其變性物、丙烯腈共聚物的變性物、聚苯醚、聚苯乙烯、聚乙烯、聚醯亞胺、氟樹脂、聚矽氧凝膠、聚矽氧油、矽烷偶合劑之填充材的表面處理劑、脫模劑、碳黑、酞菁藍、酞菁綠等著色劑。相對於硬化性樹脂組成物100質量份,此等添加劑的調配量較佳為1,000質量份以下,更佳為700質量份以下的範圍。此等添加劑的特佳成分可列舉聚丁二烯及其變性物、丁二烯系熱塑性彈性體。關於此等成分,將於以下說明詳細內容。
聚丁二烯及其變性物可列舉:聚丁二烯、羥基末端聚丁二烯、末端(甲基)丙烯酸酯化聚丁二烯、羧酸末端聚丁二烯、胺末端聚丁二烯、苯乙烯-丁二烯橡膠等,從介電特性之觀點來看,較佳為聚丁二烯或苯乙烯-丁二烯橡膠。苯乙烯-丁二烯橡膠(SBR)可列舉例如RICON-100、RICON-181、RICON-184(皆
為Cray Valley公司製)等,聚丁二烯可列舉B-1000、B-2000、B-3000(皆為Nippon Soda公司製)等。此等可單獨使用或併用兩種以上。聚丁二烯及苯乙烯-丁二烯橡膠的分子量較佳為重量平均分子量500至10000,更佳為750至7500,更佳為1000至5000。於上述範圍的下限以下時,揮發量變多,於預浸材製作時難以進行固形分的調整,於上述範圍的上限以上時,與其他硬化性樹脂之相溶性惡化。
丁二烯系熱塑性彈性體可列舉:SEP(苯乙烯-乙烯/丙烯共聚物:Septon 1020 Kuraray股份有限公司製);SEPS(苯乙烯-乙烯/丙烯-苯乙烯共聚物:Septon 2002、Septon 2004F、Septon 2005、Septon 2006、Septon 2063、Septon 2104皆為Kuraray股份有限公司製);SEEPS(苯乙烯-乙烯/乙烯-丙烯-苯乙烯嵌段共聚物:Septon 4003、Septon 4044、Septon 4055、Septon 4077、Septon 4099皆為Kuraray股份有限公司製);SEBS(苯乙烯-乙烯-丁烯-苯乙烯嵌段共聚物:Septon 8004、Septon 8006、Septon 8007L皆為Kuraray股份有限公司製);SEEPS-OH(於苯乙烯-乙烯/乙烯-丙烯-苯乙烯嵌段共聚物的末端具有羥基之化合物:Septon HG252 Kuraray股份有限公司製);SIS(苯乙烯-異戊二烯-苯乙烯嵌段共聚物:Septon 5125、Septon 5127皆為Kuraray股份有限公司製)、氫化SIS(氫化苯乙烯-異戊二烯-苯乙烯嵌段共聚物:Hybrar 7125F、Hybrar 7311F皆為Kuraray股份有限公司製)等。此等可單獨使用或併用兩種以上。由於具有更高的耐熱性且不易氧化劣化,所以於丁二烯系熱塑性彈性體中,較佳為不具有不飽和鍵者。此外,丁二烯系熱塑性彈性體的重量平均分子量只要是10000以上,就無特別限制,惟過大時,除了聚苯醚化合物之外,與重量平均分子量約50至1000的低分子量成分及重量平均分子量約1000至5000的低聚物成分之相溶性惡化,難以確保混合及溶劑穩定性,所以較佳約為10000至300000。
本發明之硬化性樹脂組成物係藉由以預定的比率來均一地混合上述各成分而得,通常是於130至180℃以30至500秒的範圍進行預硬化,然後於150至200℃以2至15小時進行後硬化以藉此進行充足的硬化反應,而得到本發明之硬化物。此外,亦可將硬化性樹脂組成物的成分均一地分散或溶解於溶劑等,然後進行去除溶劑之後硬化。
如此得到之本發明之硬化性樹脂組成物係具有耐濕性、耐熱性、高接著性。因此,本發明之硬化性樹脂組成物可使用在要求耐濕性、耐熱性、高接著性之廣泛的領域中。具體而言,係有用於作為絕緣材料、積層板(印刷配線板、BGA用基板、增層基板等)、密封材料、光阻等所有電氣及電子零件用材料。此外,除了成形材料、複合材料之外,亦可使用在塗料材料、接著劑、3D列印等領域。尤其在半導體密封中,係有益於耐回焊性。
半導體裝置係具有以本發明之硬化性樹脂組成物所密封者。半導體裝置可列舉例如:DIP(雙列直插封裝:Dual In-line Package)、QFP(四方扁平封裝:Quad Flat Package)、BGA(球柵陣列:Ball Grid Array)、CSP(晶片尺寸封裝:Chip Size Package)、SOP(小外形封裝:Small Outline Package)、TSOP(薄型小外形封裝:Thin Small Outline Package)、TQFP(薄型四方扁平封裝:Thin Quad Flat Package)等。
本發明之硬化性樹脂組成物的調製方法並無特別限定,可僅均一地混合各成分或是進行預聚物化。例如藉由在觸媒的存在下或非存在下、溶劑的存在下或非存在下加熱本發明之硬化性樹脂而進行預聚物化。同樣的,除了本發明之硬化性樹脂之外,亦可追加添加環氧樹脂、胺化合物、順丁烯二醯亞胺系化合物、氰酸酯化合物、酚樹脂、酸酐化合物等硬化劑及其他添加劑來進行預聚物
化。各成分的混合或預聚物化在溶劑的非存在時,係使用例如擠壓機、捏合機、輥等,在溶劑的存在時,係使用附攪拌裝置的反應釜等。
均一地混合之手法係使用捏合機、輥、行星式混合機等,以50至100℃之範圍內的溫度進行捏合來混合,而形成均一的樹脂組成物。所得到之樹脂組成物在經粉碎後,亦可藉由壓錠機等成型機來成型為圓柱的錠狀,或是形成為顆粒狀的各類粉體或粉狀的成型體,或是於表面支撐體上熔融此等組成物並成型為0.05mm至10mm厚度的片狀,而形成硬化性樹脂組成物成型體。所得到之成型體係成為於0至20℃不會產生黏滯之成型體,即使於-25至0℃保管1星期以上,流動性、硬化性亦幾乎不會降低。
所得到之成型體可藉由轉注成型機、壓縮成型機來成型為硬化物。
亦可將有機溶劑添加於本發明之硬化性樹脂組成物而構成為清漆狀的組成物(以下僅稱為清漆)。可視需要將本發明之硬化性樹脂組成物溶解於甲苯、二甲苯、丙酮、丁酮、甲基異丁酮、二甲基甲醯胺、二甲基乙醯胺、N-甲基吡咯啶酮等溶劑來構成為清漆,接著含浸於玻璃纖維、碳纖維、聚酯纖維、聚醯胺纖維、氧化鋁纖維、紙等基材並進行加熱,然後將經加熱乾燥所得到之預浸材進行熱壓成形,藉此可形成本發明之硬化性樹脂組成物的硬化物。此時的溶劑於本發明之硬化性樹脂組成物與該溶劑之混合物中,通常是以佔有10至70重量%,較佳為15至70重量%之量來使用。此外,若為液狀組成物,則亦可直接以例如藉由RTM方式來含有碳纖維而得到硬化性樹脂硬化物。
此外,亦可將本發明之硬化性組成物使用作為膜型組成物的改質劑。具體而言,可使用在提升B階段(B Stage)的可撓性等。此膜型樹脂組成物係將本發明之硬化性樹脂組成物作為前述硬化性樹脂組成物清漆塗佈於剝離膜
上,並在加熱下去除溶劑後,進行B階段而得到片狀的接著劑。此片狀接著劑可使用作為多層基板等的層間絕緣層。
本發明之硬化性樹脂組成物可藉由進行加熱熔融並進行低黏度化,然後含浸於玻璃纖維、碳纖維、聚酯纖維、聚醯胺纖維、氧化鋁纖維等強化纖維而得到預浸材。該具體例可列舉例如:E玻璃布、D玻璃布、S玻璃布、Q玻璃布、球狀玻璃布、NE玻璃布及T玻璃布等玻璃纖維,此外,有玻璃以外之無機物的纖維或聚對苯二甲醯對苯二胺(Kevlar(註冊商標)、DuPont股份有限公司製)、全芳香族聚醯胺、聚酯;以及聚對苯苯并噁唑(Poly Paraphenylene Benzoxazole)、聚醯亞胺及碳纖維等有機纖維,惟並不特別限定於此等。基材的形狀並無特別限定,可列舉例如織布、不織布、粗紗、切股氈等。此外,織布的編織方式為人所知者有平織、方平織、斜織等,可因應目的之用途或性能,從此等一般所知者中適當地選擇使用。此外,係適合使用將織布進行開纖處理者或是以矽烷偶合劑等進行表面處理後之玻璃織布。基材的厚度並無特別限定,較佳約為0.01至0.4mm。此外,亦可將前述清漆含浸於強化纖維並進行加熱乾燥而得到預浸材。
本實施型態之積層板係具備1片以上的上述預浸材。積層板只要具備1片以上的預浸材,就無特別限定,可具有其他任意層。積層板的製造方法可適當地應用一般所知的方法,並無特別限定。例如於覆金屬箔積層板的成形時,可使用多段模壓機、多段真空模壓機、連續成形機、高壓釜成形機等,且藉由積層上述預浸材彼此並進行加熱加壓成形而得到積層板。此時的加熱溫度並無特別限定,較佳為65至300℃,更佳為120至270℃。此外,加壓壓力並無特別限定,於加壓壓力過大時,難以調整積層板之樹脂的固形分,使品質未達穩定,
此外,壓力過小時,產生氣泡或積層間的密著性變差,故較佳為2.0至5.0MPa,更佳為2.5至4.0MPa。本實施型態之積層板可藉由具備由金屬箔所構成之層,而適合使用作為後述覆金屬箔積層板。
將上述預浸材裁切為期望的形狀,且視需要與銅箔等進行積層後,藉由壓製成形法或高壓釜成形法、薄片繞組成形法等,一面對積層物施加壓力一面將硬化性樹脂組成物進行加熱硬化,藉此可得到電氣及電子用積層板(印刷配線板)或碳纖維強化材。
本發明之硬化物可使用在成型材料、接著劑、複合材料、塗料等各種用途。由於本發明所記載之硬化性樹脂組成物的硬化物顯現出優異的耐熱性及介電特性,所以適合使用在半導體元件用密封材、液晶顯示元件用密封材、有機EL元件用密封材、印刷配線基板、增層積層板等電氣及電子零件,或是碳纖維強化塑膠、玻璃纖維強化塑膠等輕量高強度結構材用複合材料。
[實施例]
接著藉由實施例來更具體地說明本發明。以下在未特別言明時,份為重量份。本發明並不限定於此等實施例。
下列係說明實施例中所使用之各種分析方法。
〈重量平均分子量(Mw)〉
使用聚苯乙烯標準液並藉由聚苯乙烯換算來算出。
GPC:DGU-20A3R、LC-20AD、SIL-20AHT、RID-20A、SPD-20A、CTO-20A、CBM-20A(皆為島津製作所公司製)
管柱:Shodex KF-603、KF-602×2、KF-601×2)
連結溶析液:四氫呋喃
流速:0.5ml/min.
管柱溫度:40℃
檢測:RI(微差折射檢測器)
[實施例1]
將2-溴乙基苯(東京化成公司製)37.0份、4,4'-二氯對二甲苯(東京化成公司製)17.5份、二苯基甲烷8.4份、甲烷磺酸(東京化成公司製)3.2份饋入安裝有溫度計、冷卻管、攪拌機之燒瓶,並於130℃進行5小時的反應。於放置冷卻後,藉由甲苯200份進行萃取並以水100份將有機層洗淨5次。於加熱減壓下餾除溶劑及過剩的2-溴乙基苯,而得到作為液狀樹脂之具有2-溴乙基苯結構之烯烴樹脂前驅物(BEB-1)31.9份(Mn:884、Mw:1327)。將所得到之化合物的GPC圖呈示於圖1。此外,將所得到之化合物的1H-NMR圖(氘化三氯甲烷)呈示於圖2。於1H-NMR圖的3.05-3.60ppm觀測到來自溴乙基之訊號。
[實施例2]
將實施例1中所得到之BEB-1(25.0份)、甲苯20份、二甲基亞碸60份、4-羥基-2,2,6,6-四甲基哌啶-1-氧基(東京化成公司製)0.0125份、50wt%氫氧化鈉水溶液12.0份加入安裝有溫度計、冷卻管、攪拌機之燒瓶,並於40℃進行6小時的反應。接著加入水100份並將有機層進行水洗以去除生成鹽。然後將有機層再次送回反應容器,於40℃進行1小時的反應。於放置冷卻後,加入甲苯100份
並以水100份將有機層洗淨5次,於加熱減壓下餾除溶劑,而得到具有苯乙烯結構作為官能基之高黏稠液狀烯烴樹脂(O-1)15.4份(Mn:809、Mw:1363)。將反應結束時的GPC圖呈示於圖3。此外,將所得到之化合物的1H-NMR數據(氘化三氯甲烷)呈示於圖4。於1H-NMR圖的5.10-5.30ppm、5.50-5.75ppm及6.60-6.80ppm觀測到來自乙烯基之訊號。O-1之單核體的含量為13.6%,O-1中所含之前述式(4-a)所表示之化合物的含量以GPC(RI)面積%計為23.7%,α/β=0.57。
[實施例3]
將2-溴乙基苯(東京化成公司製)37.0份、4,4'-二氯對二甲苯(東京化成公司製)17.5份、二苯醚8.5份、甲烷磺酸(東京化成公司製)3.2份饋入安裝有溫度計、冷卻管、攪拌機之燒瓶,並於130℃進行5小時的反應。於放置冷卻後,藉由甲苯200份進行萃取並以水100份將有機層洗淨5次。於加熱減壓下餾除溶劑及過剩的2-溴乙基苯,而得到作為半固形樹脂之具有2-溴乙基苯結構之烯烴樹脂前驅物(BEB-2)26.5份(Mn:947、Mw:1480)。將所得到之化合物的GPC圖呈示於圖5。此外,將所得到之化合物的1H-NMR圖(氘化三氯甲烷)呈示於圖6。於1H-NMR圖的3.00-3.60ppm觀測到來自溴乙基之訊號。
[實施例4]
將實施例3中所得到之BEB-2(25.0份)、甲苯20份、二甲基亞碸60份、4-羥基-2,2,6,6-四甲基哌啶-1-氧基(東京化成公司製)0.0125份、50wt%氫氧化鈉水溶液12.0份加入安裝有溫度計、冷卻管、攪拌機之燒瓶,並於40℃進行6小時的反應。接著加入水100份並將有機層進行水洗以去除生成鹽。然後將有機層再次送回反應容器,於40℃進行1小時的反應。於放置冷卻後,加入甲苯100份並以水100份將有機層洗淨5次,於加熱減壓下餾除溶劑,而得到具有苯乙烯結構作為官能基之高黏稠液狀烯烴樹脂(O-2)14.8份(Mn:880、Mw:1541)。將反應結束時的GPC圖呈示於圖7。此外,將所得到之化合物的1H-NMR數據(氘化三氯甲烷)呈示於圖8。於1H-NMR圖的5.10-5.30ppm、5.50-5.75ppm及6.60-6.80ppm觀測到來自乙烯基之訊號。O-2之單核體的含量為14.2%,O-2中所含之前述式(4-a)所表示之化合物的含量以GPC(RI)面積%計為21.7%,α/β=0.65。
[實施例5、6、7]
以表1的比率(質量份)來調配實施例2、4中所得到之化合物(O-1、O-2)、SA-9000(甲基丙烯酸酯末端聚苯醚、SABIC公司製)、Ricon-100(苯乙烯-丁二烯橡膠、Cray Valley公司製)、以及DCP(過氧化二異丙苯、Kayaku Nouryon公司製),於金屬容器中進行加熱熔融並混合,然後直接注入模具並於220℃進行1小時的硬化,而進行各種試驗。將測定結果呈示於表1。
[比較例1]
以表1的比率(質量份)來調配聯苯芳烷基型環氧樹脂(NC-3000日本化藥股份有限公司製)、酚-酚醛清漆型酚樹脂(PN(H-1)軟化點80℃明和化成工業股份有限公司製))、以及作為硬化促進劑的TPP(三苯基膦東京化成公司製),於金屬容器中進行加熱熔融並混合,然後直接注入於模具並以175℃進行轉注成型後,於160℃進行2小時並於180℃使硬化6小時,而進行各種試驗。將測定結果呈示於表1。
〈耐熱性試驗〉
.玻璃轉移溫度:藉由動態黏彈性試驗機進行測定,tanδ為最大值時之溫度。
動態黏彈性測定器:TA-Instruments公司製DMA-2980
升溫速度:2℃/分鐘
測定頻率:10Hz
〈介電常數試驗及介電正切試驗〉
.使用AET開發股份有限公司製的10GHz空腔共振器,藉由空腔共振擾動法來進行測試。
從表1中,已確認實施例5、6單獨地硬化。此外,已確認實施例5、6、7與以往所使用之環氧系樹脂組成物相比,具有優異的耐熱性與介電特性。
[參考例1]
將2-溴乙基苯(東京化成公司製)296份、α,α'-二氯對二甲苯(東京化成公司製)70份、甲烷磺酸(東京化成公司製)18.4份饋入安裝有溫度計、冷卻管、攪拌機之燒瓶,並於130℃進行8小時的反應。於放置冷卻後,以氫氧化鈉水溶液進行中和,然後藉由甲苯1200份進行萃取並以水100份將有機層洗淨5次。於加熱減壓下餾除溶劑及過剩的2-溴乙基苯,而得到作為液狀樹脂之具有2-溴乙基
苯結構之化合物前驅物(BEB-3)160份(Mn:538、Mw:649)。將反應式呈示於下一段落。將所得到之化合物的GPC圖呈示於圖9。從GPC圖的面積%所計算之重複單元n為1.7。此外,將所得到之化合物的1H-NMR圖(DMSO-d6)呈示於圖10。於1H-NMR圖的2.95-3.15ppm及3.60-3.75ppm觀測到來自溴乙基之訊號。
[參考例2]
將參考例1中所得到之BEB-3 22份、甲苯50份、二甲基亞碸150份、水15份、氫氧化鈉5.4份加入安裝有溫度計、冷卻管、攪拌機之燒瓶,並於40℃進行5小時的反應。於放置冷卻後,加入甲苯100份並以水100份將有機層洗淨5次,於加熱減壓下餾除溶劑,而得到具有苯乙烯結構作為官能基之液狀化合物(O-3)13份(Mn:432、Mw:575)。將反應式呈示於下一段落。將所得到之化合物的GPC圖呈示於圖11。從GPC圖的面積%所計算之重複單元n為1.7。此外,將所得到之化合物的1H-NMR數據(DMSO-d6)呈示於圖12。於1H-NMR圖的5.10-5.30ppm、5.50-5.85ppm及6.60-6.80ppm觀測到來自乙烯基之訊號。
[實施例8、9、比較例2]
分別量取2份之實施例2、4中所得到之烯烴樹脂(O-1、O-2)以及參考例2中所得到之烯烴樹脂(O-3)。將各烯烴樹脂塗佈於福田金屬銅箔公司製之低粗度銅箔(T-4X、厚度18μm)的霧面後,使用將緩衝紙的中央部挖空15cm見方者(硬化後膜厚成為300μm之厚度)作為間隔材,並以從該上方使福田金屬銅箔公司製之低粗度銅箔(T-4X、厚度18μm)的霧面接觸於樹脂之方式來重疊。使用真空模壓機,在施加真空化1MPa的壓力下以220℃進行1小時的硬化。將使用此樣本來測試銅箔密著性之結果呈示於表2。
[密著性評估判定基準]
○:在無蝕刻下無法從銅箔中剝離
×:即使無蝕刻亦可從銅箔中剝離
從表2來看,係表示實施例8、9與比較例2相比,其密著性優異。
以上係參照特定樣態來詳細地說明本發明,對該業者而言可明瞭的是,在不脫離本發明之精神與範圍下可進行各種變更及修正。
本申請案係根據2021年3月4日提出申請之日本國專利申請案(日本特願2021-034159及日本特願2021-034160),藉由引用來援引該整體內容。此外,在此應予引用之參照內容係以整體來納入。
[產業上之可應用性]
本發明之化合物係有用於電氣及電子零件用絕緣材料(高可靠度半導體密封材料等)及積層板(印刷配線板、BGA用基板、增層基板等)、接著劑(導電性接著劑等)或包含CFRP之各種複合材料用、塗料、3D列印等用途。
Claims (11)
- 如請求項1所述之化合物,其中於前述式(1)中,n為1.1≦n≦20。
- 如請求項3所述之化合物,其中於前述式(1)中,X為前述式(2)中所記載之(a)。
- 一種硬化性樹脂組成物,係含有如請求項1至4中任一項所述之化合物或是如請求項5所述之混合物。
- 如請求項6所述之硬化性樹脂組成物,其更含有選自由聚苯醚、聚丁二烯及其變性物所組成之群組中的1種以上。
- 如請求項7所述之硬化性樹脂組成物,其中前述聚丁二烯及其變性物係含有選自由苯乙烯/丁二烯共聚物及丁二烯系熱塑性彈性體所組成之群組中的1種以上。
- 一種硬化物,係將如請求項1至4中任一項所述之化合物、如請求項5所述之混合物或是如請求項6至8中任一項所述之硬化性樹脂組成物進行硬化而得。
- 一種如請求項1至4中任一項所述之化合物的製造方法,係包含:在鹼性觸媒的存在下,將如請求項10所述之前述式(3)所表示之化合物進行脫鹵氫反應之步驟。
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JP4971601B2 (ja) * | 2005-07-05 | 2012-07-11 | 新日鐵化学株式会社 | ビニルベンジルエーテル化合物及び該化合物を必須成分とする樹脂組成物 |
JP5521188B2 (ja) | 2008-11-07 | 2014-06-11 | 国立大学法人神戸大学 | センシングチップ、その製造方法およびその利用 |
CN105086417B (zh) | 2014-05-06 | 2017-09-12 | 广东生益科技股份有限公司 | 一种树脂组合物及其在高频电路板中的应用 |
CN106795276B (zh) | 2014-07-01 | 2019-09-24 | 明和化成株式会社 | 烯丙基醚或烯丙基改性联苯芳烷基酚醛清漆树脂、其制造方法和使用了它的组合物 |
KR102201795B1 (ko) | 2016-12-16 | 2021-01-14 | 노보셋, 엘엘씨 | 수지 조성물 |
CN110845853B (zh) | 2019-12-09 | 2021-11-26 | 苏州生益科技有限公司 | 树脂组合物及具有其的半固化片、层压板、绝缘板、电路基板、覆盖膜 |
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2022
- 2022-02-24 JP JP2022541781A patent/JP7241246B2/ja active Active
- 2022-02-24 WO PCT/JP2022/007527 patent/WO2022186030A1/ja active Application Filing
- 2022-02-24 KR KR1020237029210A patent/KR20230154819A/ko unknown
- 2022-03-02 TW TW111107557A patent/TW202244107A/zh unknown
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Publication number | Priority date | Publication date | Assignee | Title |
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TWI843461B (zh) * | 2022-12-21 | 2024-05-21 | 台光電子材料股份有限公司 | 預聚物、包含其之樹脂組合物及其製品 |
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KR20230154819A (ko) | 2023-11-09 |
JP7241246B2 (ja) | 2023-03-16 |
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