CN106188538A - 改性苯并噁嗪树脂、其组合物及应用 - Google Patents
改性苯并噁嗪树脂、其组合物及应用 Download PDFInfo
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- CN106188538A CN106188538A CN201510295056.9A CN201510295056A CN106188538A CN 106188538 A CN106188538 A CN 106188538A CN 201510295056 A CN201510295056 A CN 201510295056A CN 106188538 A CN106188538 A CN 106188538A
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Abstract
本发明提供下式(1)或(2)所示的改性苯并噁嗪化合物、其组合物及其应用,式中R、R’、A、B、m、n、a1、a2、a3和b如文中所定义。本发明还涉及该苯并噁嗪化合物的制备方法,以及由该组合物制成的制品。
Description
【技术领域】
本发明涉及一种改性苯并噁嗪化合物及其制造方法,尤指一种应用于铜箔基板及印刷电路板的改性苯并噁嗪化合物。
【背景技术】
随着电子科技的高速发展,移动通讯、服务器、云端储存等电子产品的信息处理不断向「信号传输高频化和高速数字化」的方向发展,低介电树脂材料因此成为现今高传输速率基板的主要开发方向,以满足云端科技、终端服务器所需高速信息传输处理的要求。因此对于覆铜板(或称积层板、铜箔基板,copper clad laminate(CCL))的要求主要表现在材料需具备高可靠性、高耐湿热性、低介电常数、低介电损耗、高尺寸稳定性等方面。因此,必须寻找介电性能更优异的高性能覆铜板材料,用以制作高性能的印刷电路板(PCB)。
苯并噁嗪化合物具有良好的耐热性质及机械性质等优点,台湾专利公告第308566号揭示使用苯并噁嗪化合物及热固性树脂所形成的树脂组合物,用以制做积层板。台湾专利公告第460537号揭示使用苯并噁嗪化合物及苯酚酚醛树脂所形成的组合物,制做积层板。台湾专利公告第583258号揭示使用苯并噁嗪化合物及三氮杂苯酚醛树脂所形成的组合物,制做积层板。台湾专利公告第I311568号揭示使用苯并噁嗪化合物与苯乙烯-顺丁烯二酸酐共聚物制做积层板。但是习知现有使用的苯并噁嗪化合物(例如:双酚A型苯并噁嗪、双酚F型苯并噁嗪)仍具有下述的缺点包含:具有相对较低的玻璃转化温度(Tg)、相对较差的介电性质,无法满足新一代高性能的更低介电、更高玻璃转化温度的需求。因此提出一种具相对较高玻璃转化温度及相对较佳介电性质的苯并噁嗪化合物,以使所制成的积层板为高频高速传输PCB使用的更理想材料。
【发明内容】
鉴于上述现有技术的缺憾,本发明提供一种改性苯并噁嗪化合物,其可使用于树脂组合物中。该树脂组合物可用于制造半固化片(prepreg)或树脂膜(resin film)。以该半固化片或树脂膜所制成的铜箔基板及印刷电路板具有低介电常数、低介电损耗、高耐热性及高阻燃性等特性。
为达上述目的,本发明提供一种改性苯并噁嗪化合物,其具有如式(1)或式(2)所示的结构:
其中,R可为脂肪族烃基(例如:烷基、环烷基、烯基)或芳香基(例如:苯基、苄基);R’选自亚氨基、烯丙基、C1至C20(即1至20个碳原子)的脂肪族烃基(例如:烷基、环烷基、烯基)、二环戊二烯基或芳香基(例如:苯基、苄基)所组成的群组;其中较佳为:烯丙基、C1至C8烷基、C3至C8环烷基、苯基或苄基,且R’基团可进一步经1至4个取代基取代。其中,m可为0至4的整数,n可为0或1;A可各选自-CH2-、-CH(CH3)-、及-C(CH3)2-,且各个A可相同或不同;B为亚芳基(例如:亚苯基、亚苄基),更进一步,B为经取代的亚芳基(例如:溴化亚苯基、溴化亚苄基);a1、a2、a3及b可各自分别为0或1。
在一实施方式中,本发明改性苯并噁嗪化合物为式(1),其中a1=0、a2=0、a3=0、b=0、m=0且n=0,且R’为苯基。在另一实施方式中,本发明改性苯并噁嗪化合物为式(2),其中a1=0、a2=0、a3=0、b=0、m=0且n=0,且R’为苯基。在又一实施方式中,本发明改性苯并噁嗪化合物为式(1)或式(2),其中a1=0、a2=0、a3=0、b=1、m=0及n=0,且B为亚苯基(-C6H4-),且R’为苯基。于再一实施方式中,本发明改性苯并噁嗪化合物为式(1)或式(2),其中a1=0、a2=1、a3=0、b=1、m=0及n=0,且A为-C(CH3)2-,B为亚苯基(-C6H4-),且R’为苯基。于又再一实施方式中,本发明改性苯并噁嗪化合物为式(1)或式(2),其中a1=1、a2=0、a3=1、b=1、m=0及n=0,且A皆为亚甲基(-CH2-),B为亚苯基(-C6H4-),且R’为苯基。
在较佳的实施方式中,本发明改性苯并噁嗪化合物为选自由下列式(6)、式(7)、式(8)、式(9)、及式(10)所示化合物所组成的群组:
本发明另提供一种制造改性苯并噁嗪化合物的方法,其包含:将苯二醛化合物与氨基酚化合物加入溶剂中,于100至150℃反应3至5小时形成甲亚胺(azomethine)基酚;接着,甲亚胺基酚与伯胺及甲醛于70至100℃反应5至8小时,以获得改性苯并噁嗪化合物。
上述方法中,该苯二醛化合物具有如式(3)的结构式:
其中,R可为脂肪族烃基(例如:烷基、环烷基、烯基)或芳香基(例如:苯基、苄基),m可为0至4的整数;A可选自-CH2-、-CH(CH3)-、及-C(CH3)2-所组成的群组,且两个A可相同或不同;B可为亚芳基(例如:亚苯基、亚苄基),更进一步,B为经取代的亚芳基(例如:溴化亚苯基、溴化亚苄基);a1至a3及b可各自分别为0或1。
举例而言,该苯二醛化合物可为邻苯二醛、间苯二醛、对苯二醛、4,6-二甲基异酞二醛(4,6-dimethylisophthalic dialdehyde)(CAS编号:25445-41-4)、4-甲基异酞醛(4-methylisophthalaldehyde)(CAS编号:23038-58-6)、或4,4’-联苯二甲醛(CAS编号:66-98-8)。
较佳的苯二醛化合物选自邻苯二醛、间苯二醛、及对苯二醛。
在上述方法中,该氨基酚化合物可选自至少一种如下式(4)或(5)所示的化合物,但并不以此为限:
其中,R各独立选自氢、脂肪族烃基(例如:烷基、环烷基、烯基)及芳香基(例如:苯基、苄基);A选自-CH2-、-CH(CH3)-、-C(CH3)2-、脂肪族亚烃基、及亚芳基;n可为0或1。
该氨基酚化合物实例包括但不限于2-氨基苯酚、3-氨基苯酚、4-氨基苯酚、2,4-二氨基苯酚(2,4-diaminophenol(CAS编号:95-86-3))、2,6-二氯对氨基苯酚(CAS编号:5930-28-9)、6-氨基-2-萘酚(6-amino-2-naphthol,CAS编号:56961-71-8)、或8-氨基-2-萘酚(8-amino-2-naphthol,CAS编号:118-46-7)。
较佳的氨基酚化合物选自:2-氨基苯酚、3-氨基苯酚,4-氨基苯酚、6-氨基-2-萘酚、及8-氨基-2萘酚。
上述方法中,该伯胺选自通式R’NH2所示的伯胺,其中,R’选自亚氨基、烯丙基、C1至C20脂肪族官能基(例如:烷基、环烷基或烯基)、二环戊二烯基及芳香基(例如:苯基、苄基)所组成的群组;其中较佳为:烯丙基、C1至C8烷基、C3至C8环烷基、苯基或苄基。其中,R’基团上可进一步经1至4个取代基取代。
该伯胺化合物实例包括但不限于:苯胺、邻苯二胺、间苯二胺、对苯二胺、联苯二胺、4,4’-二氨基二苯甲烷、环己胺、丁胺、甲胺、己胺、烯丙胺(allylamine,CAS编号:107-11-9)、或丙二胺。
较佳的伯胺选自:苯胺、环己胺、丁胺、甲胺、己胺、及烯丙胺。
上述方法中,该溶剂选自二甲亚砜、二甲基甲酰胺、二甲基乙酰胺、甲苯、二甲苯中的一种或其组合。
依上述顺序、条件进行反应后,可得到改性苯并噁嗪。举例而言,所得产物可具有如上述式(6)、式(7)、式(8)、式(9)或式(10)的结构,但本发明的改性苯并噁嗪并不限于此。
本发明所述的改性苯并噁嗪化合物相较于一般苯并噁嗪化合物至少具有下列优点:低介电损耗及高耐热性(例如:高玻璃转化温度)。
本发明另一目的是提供一种低介电耗损的树脂组合物,其包含:(A)改性苯并噁嗪化合物;及(B)交联剂。
本发明所述的改性苯并噁嗪化合物可为其单体组合、或其预聚物。
本发明所述的交联剂可为下列其中一种或其组合:环氧树脂、氰酸脂树脂、异氰酸酯、聚苯醚树脂、马来酰亚胺、聚酰胺(polyamide)、聚酰亚胺(polyimide)、酚氧树脂(phenoxy resin)、苯乙烯马来酸酐共聚物、聚酯、烯烃聚合物、酚树脂、胺类硬化剂、酸酐硬化剂或二烯丙基双酚A(diallyl bisphenol A)。
本发明所述的环氧树脂可为下列其中一种或其组合:双酚A(bisphenol A)环氧树脂、双酚F(bisphenol F)环氧树脂、双酚S(bisphenol S)环氧树脂、双酚AD(bisphenolAD)环氧树脂、酚醛(phenol novolac)环氧树脂、双酚A酚醛(bisphenol A novolac)环氧树脂、双酚F酚醛(bisphenolF novolac)环氧树脂、邻甲酚(o-cresol novolac)环氧树脂、三官能性(trifunctional)环氧树脂、四官能性(tetrafunctional)环氧树脂、多官能性(multifunctional)环氧树脂、二环戊二烯(dicyclopentadiene,DCPD)环氧树脂、含磷环氧树脂、DOPO环氧树脂、DOPO-HQ环氧树脂、对二甲苯环氧树脂(p-xylene epoxy resin)、萘型(naphthalene)环氧树脂、苯并哌喃型(benzopyran)环氧树脂、联苯酚醛(biphenyl novolac)环氧树脂、异氰酸酯改质(isocyanate modified)环氧树脂、酚苯甲醛(phenolbenzaldehyde epoxy)环氧树脂及酚基芳烷基酚醛(phenolaralkyl novolac)环氧树脂。其中,DOPO环氧树脂可为DOPO-PN环氧树脂、DOPO-CNE环氧树脂、DOPO-BPN环氧树脂,DOPO-HQ环氧树脂可为DOPO-HQ-PN环氧树脂、DOPO-HQ-CNE环氧树脂、DOPO-HQ-BPN环氧树脂。
本发明所述的氰酸酯树脂(cyanate ester resin)包括但不限于:具有Ar-O-C≡N结构的氰酸酯树脂,其中Ar可为经取代或未经取代的芳香基;酚醛型氰酸酯树脂、双酚A型氰酸酯树脂、双酚A酚醛型氰酸酯树脂、双酚F型氰酸酯树脂、双酚F酚醛型氰酸酯树脂、含双环戊二烯结构的氰酸酯树脂、含萘环结构的氰酸酯树脂或酚酞型氰酸酯树脂。
该氰酸酯树脂的实例包括但不限于:商品名为Primaset PT-15、PT-30S、PT-60S、CT-90、BADCY、BA-100-10T、BA-200、BA-230S、BA-300S、BTP-2500、BTP-6020S、DT-4000、DT-7000、Methylcy、ME-240S等由Lonza生产的氰酸酯树脂。
本发明所述的异氰酸酯包括但不限于下列其中一种或其组合:1,4-环己烷二异氰酸酯、异佛尔酮二异氰酸酯(isophorone diisocyanate)、亚甲基双(4-环己基异氰酸酯)(methylene bis(4-cyclohexylisocyanate))、三烯丙基异氰脲酸酯、氢化1,3-苯撑二甲基二异氰酸酯、及氢化1,4-苯撑二甲基二异氰酸酯。较佳的是,该异氰酸酯为三烯丙基异氰脲酸酯。
本发明所述的聚苯醚树脂较佳选自下列群组中至少一种或其组合,但并不以此为限:双羟基聚苯醚(例如SA-90,可购自Sabic)、双乙烯苄基聚苯醚树脂(例如OPE-2st,可购自三菱瓦斯化学)、乙烯基苄基化的改性双酚A聚苯醚、甲基丙烯酸聚苯醚树脂(例如SA-9000,可购自Sabic)。
本发明所述的马来酰亚胺包括但不限于下列其中一种或其组合:4,4’-二苯甲烷双马来酰亚胺(4,4’-diphenylmethane bismaleimide)、苯甲烷马来酰亚胺寡聚物(oligomer of phenylmethane maleimide)、间亚苯基双马来酰亚胺(m-phenylene bismaleimide)、双酚A二苯基醚双马来酰亚胺(bisphenol A diphenyl ether bismaleimide)、3,3’-二甲基-5,5’-二乙基-4,4’-二苯基甲烷双马来酰亚胺(3,3’-dimethyl-5,5’-diethyl-4,4’-diphenylmethanebismaleimide)、4-甲基-1,3-亚苯基双马来酰亚胺(4-methyl-1,3-phenylene bismaleimide)及1,6-双马来酰亚胺-(2,2,4-三甲基)己烷(1,6-bismaleimide-(2,2,4-trimethylhexane))。
本发明所述的酚氧树脂是指具有以酚氧基或其衍生物基作为骨架的树脂,可将双酚化合物或其衍生物与环氧氯或其衍生物进行反应,藉由习知方法制造而得。
该酚氧树脂的实例包括但不限于:E1255HX30(双酚A骨架)、E1256B40(双酚A骨架)、E4256H40(双酚F骨架)、E5580BPX40、YX8100BH30、YL6954BH30,由日本环氧树脂制造;ERF001,由东都化成制造;RX200,太阳墨水制造。
本发明所述的苯乙烯马来酸酐共聚物中,苯乙烯(S)与马来酸酐(MA)的比例可为1/1、2/1、3/1、4/1、6/1或8/1,如Cray valley贩卖的商品名SMA-1000、SMA-2000、SMA-3000、EF-30、EF-40、EF-60及EF-80等苯乙烯马来酸酐共聚物。此外,所述苯乙烯马来酸酐共聚物亦可为酯化苯乙烯马来酸酐共聚物,如商品名SMA1440、SMA17352、SMA2625、SMA3840及SMA31890。用于添加至本发明的树脂组合物中的苯乙烯马来酸酐共聚物可为上述其中一种或其组合。
本发明所述的聚酯树脂由具有二羧酸基的芳香族与具有二羟基的芳香族酯化而成,如可购自大日本油墨化学的HPC-8000T65。
本发明所述的烯烃聚合物可为下列其中一种或其组合:苯乙烯-丁二烯-二乙烯基苯三元聚合物、苯乙烯-丁二烯-马来酸酐三元聚合物、乙烯基-聚丁二烯-胺甲酸乙酯寡聚物(vinyl-polybutadiene-urethane oligomer)、苯乙烯丁二烯共聚物、氢化苯乙烯丁二烯共聚物、苯乙烯异戊二烯共聚物、氢化苯乙烯异戊二烯共聚物的至少一种或其组合。
所述的烯烃聚合物较佳选自苯乙烯-丁二烯-二乙烯基苯三元聚合物、苯乙烯-丁二烯-马来酸酐三元聚合物、乙烯基-聚丁二烯-尿酯寡聚物或其组合。
本发明所述的酚树脂可为单官能、双官能或多官能酚树脂,上述酚树脂并无限定使用种类,目前业界使用的酚树脂皆为本发明所述的酚树脂范围。
本发明所述的胺类硬化剂具有氨基(amino)的树脂,较佳具有二氨基官能团(diamino)的树脂。更具体而言,胺类硬化剂可为二氨基二苯砜(diamino diphenyl sulfone)、二氨基二苯基甲烷(diamino diphenyl methane)、二氨基二苯醚(diamino diphenyl ether)、二氨基二苯硫醚(diaminodiphenyl sulfide)、双氰胺(dicyandiamide,DICY)中的一种或其组合。其中,所述胺类硬化剂较佳选自4,4’-二氨基二苯砜(4,4’-diamino diphenyl sulfone)、4,4’-二氨基二苯基甲烷(4,4’-diamino diphenyl methane)、4,4’-二氨基二苯醚(4,4’-diamino diphenyl ether)、4,4’-二氨基二苯硫醚(4,4’-diamino diphenyl sulfide)、双氰胺(dicyandiamide,DICY)中的一种或其组合。
本发明所述的酸酐硬化剂(anhydride-based hardeningagent)可为液态、固态或多官能酸酐硬化剂,上述酸酐硬化剂并无限定使用种类,目前业界使用的酸酐硬化剂皆为本发明所述的酸酐硬化剂范围。
本发明所述的树脂组合物,可进一步包含性质调整剂,用以调整树脂组合物的至少一种以下性质:阻燃性、耐热性、介电常数、介电损耗、韧性、反应性、黏度及溶解性。
在本发明的一个实施方式中,所述的性质调整剂选自由阻燃剂、硬化促进剂、无机填料、表面活性剂、增韧剂、溶剂及其组合所组成的群组。
本发明所述的阻燃剂可为含磷阻燃剂或溴化阻燃剂,其中该溴化阻燃剂并无特别限制,较佳选自下列群组中至少一种:乙基-双(四溴苯邻二甲酰亚胺)(如购自Albemarle的SAYTEX BT-93)、乙烷-1,2-双(五溴苯)(如购自Albemarle的SAYTEX 8010)及2,4,6-参(2,4,6-三溴苯氧基)-1,3,5-三嗪(2,4,6-Tris(2,4,6-tribromophenoxy)-1,3,5-triazine,如ICL Industrial公司生产的商品FR-245)。该含磷阻燃剂并无限制,较佳选自下列群组中至少一种:双酚A二苯基磷酸酯(bisphenol A bis-(diphenylphosphate))、多磷酸铵(ammoniumpolyphosphate)、对苯二酚-双-(二苯基磷酸酯)(hydroquinone bis-(diphenyl phosphate))、双酚A双-(二苯基磷酸酯)(bisphenol A bis-(diphenylphosphate))、三(2-羧乙基)膦(tri(2-carboxyethyl)phosphine(TCEP))、磷酸参(氯异丙)酯、磷酸三甲酯(trimethyl phosphate(TMP))、甲基膦酸二甲酯(dimethyl methyl phosphonate(DMMP))、间苯二酚双-(二甲苯基磷酸酯)(resorcinol bis(dixylenylphosphate)(RDXP),如PX-200(即间苯二酚双-(二-(2,6-甲苯基)磷酸酯))(resorcinol bis(di-(2,6-xylenyl)phosphate)))、磷腈化合物(phosphazenes,如SPB-100)、多磷酸三聚氰胺(melamine polyphosphate)、9,10-二氢-9-氧杂-10-磷菲-10-氧化物(9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide(DOPO))及其衍生物或树脂、三聚氰胺三聚氰酸化合物(melamine cyanurate)及三羟乙基异氰尿酸酯(tri-hydroxy ethyl isocyanurate)。但,本发明所述的阻燃剂并不以此为限,举例来说,阻燃剂可为DOPO化合物、DOPO树脂(如DOPO-HQ、DOPO-NQ、DOPO-PN、DOPO-BPN)、DOPO键结的环氧树脂等,其中DOPO-PN为DOPO-phenolic novolac、DOPO-BPN可为DOPO-BPAN(DOPO-bisphenol A novolac)、DOPO-BPFN(DOPO-bisphenol F novolac)、DOPO-BPSN(DOPO-bisphenolS novolac)等双酚酚醛化合物。
本发明的树脂组合物可进一步包含硬化促进剂以增加树脂组合物的反应速率。该硬化促进剂可包含路易斯碱或路易斯酸等催化剂(catalyst),其中,路易斯碱可包含咪唑(imidazole)、三氟化硼胺复合物、氯化乙基三苯基鏻(ethyltriphenyl phosphonium chloride)、2-甲基咪唑(2-methylimidazole(2MI))、2-苯基咪唑(2-phenyl-1H-imidazole(2PZ))、2-乙基-4-甲基咪唑(2-ethyl-4-methylimidazole(2E4MI))、三苯基膦(triphenylphosphine(TPP))与4-二甲基氨基吡啶(4-dimethylaminopyridine(DMAP))中一种或多种。该路易斯酸可包含金属盐类化合物,如锰、铁、钴、镍、铜、锌等金属盐化合物,如辛酸锌、辛酸钴等金属催化剂。
本发明的树脂组合物可进一步包含无机填料以增加树脂组合物的热传导性、改良其热膨胀性及机械强度等特性。无机填料较佳均匀分布于该树脂组合物中。该无机填料可包含二氧化硅(熔融态、非熔融态、多孔质或中空型)、氧化铝、氢氧化铝、氧化镁、氢氧化镁、碳酸钙、氮化铝、氮化硼、碳化铝硅、碳化硅、二氧化钛、氧化锌、氧化锆、云母、勃姆石(boehmite,AlOOH)、煅烧滑石、滑石、氮化硅、煅烧高岭土。且无机填料可为球型、纤维状、板状、粒状、片状或针须状,并可任意经由硅烷或硅氧烷系硅烷偶合剂预处理。无机填料可为粒径100μm以下颗粒粉末,且较佳为粒径1nm至20μm颗粒粉末,最佳为粒径1μm以下奈米尺寸颗粒粉末。
本发明的树脂组合物可进一步包含表面活性剂以使无机填料可以均匀分散于树脂组合物中。该表面活性剂可包含硅烷化合物(silanes)及硅氧烷化合物(siloxanes)。
本发明的树脂组合物可进一步包含增韧剂以改善树脂组合物的韧性,其中,该增韧剂可包含橡胶(rubber)树脂、羧基封端丁二烯丙烯腈橡胶(carboxyl-terminatedbutadiene acrylonitrile(CTBN)rubber)、或核壳聚合物(core-shell polymer)等。
本发明的树脂组合物可进一步包含溶剂以改变树脂组合物的固含量,并调整树脂组合物的黏度,其中,该溶剂可包含甲醇、乙醇、乙二醇单甲醚、丙酮、丁酮(甲基乙基酮)、甲基异丁基酮、环己酮、甲苯、二甲苯、甲氧基乙基乙酸酯、乙氧基乙基乙酸酯、丙氧基乙基乙酸酯、乙酸乙酯、二甲基甲酰胺、丙二醇甲基醚或其混合。
本发明的树脂组合物可进一步混合使用以下苯并噁嗪树脂的其中一种或其组合:双酚A型苯并噁嗪树脂、双酚F型苯并噁嗪树脂或酚酞型苯并噁嗪树脂、双环戊二烯苯并噁嗪树脂、含磷苯并噁嗪树脂,如Huntsman生产的商品名LZ-8270、LZ-8280或LZ-8290;昭和高分子公司生产的商品名HFB-2006M。
本发明另又提供一种半固化片(即预浸片,prepreg),由前述树脂组合物所制造而得,具有低介电损耗及高耐热性(例如:高玻璃转化温度)等特性。据此,本发明所揭露半固化片可包含补强材及前述树脂组合物,其中该树脂组合物以浸渍(impregnation)等方式附着于该补强材上,并经由高温加热形成半固化态。其中,补强材可为纤维材料、织布及不织布,如玻璃纤维布等,其可增加该半固化片机械强度。此外,该补强材可任意地经由硅烷偶合剂进行预处理。
其中,补强材可为纤维材料、织布及不织布,如玻璃纤维布等,其可增加该半固化片机械强度。此外,该补强材可选择性经由硅烷偶合剂进行预处理。
前述半固化片经由高温加热或高温且高压下加热可固化形成固化胶片或是固态绝缘层,其中树脂组合物若含有溶剂,则该溶剂会于高温加热程序中挥发移除。
本发明另一目的是提供一种树脂膜(resin film),由前述树脂组合物所制造而得,具有低介电损耗及高耐热性(高玻璃转化温度)等特性。该树脂膜包含上述树脂组合物。该树脂膜可涂布于PET膜(polyester film)、PI膜(polyimide film)上,或是涂布于铜箔上(即形成经树脂涂覆铜(resin coated copper)(RCC))再经由烘烤加热而成。
本发明又一目的为提供一种由前述半固化片或树脂膜所制造而得的积层板(laminate),如铜箔基板(copper cladlaminate),其具有低介电损耗及高耐热性(例如:高玻璃转化温度)等特性,且特别适用于高速度高频率讯号传输电路板。据此,本发明提供一种积层板,其包含两个或两个以上金属箔及至少一绝缘层。其中,金属箔例如为铜箔,可进一步包含铝、镍、铂、银、金等至少一种金属合金;绝缘层由前述半固化片或是树脂膜于高温高压下固化而成,如将前述半固化片迭合于两个金属箔间且于高温与高压下进行压合而成。
本发明的积层板至少具有以下优点之一:低介电损耗及高耐热性(例如:高玻璃转化温度)。该积层板进一步经由制作线路等制程加工后,可形成一电路板,且该电路板与电子组件接合后于高温、高湿度等严苛环境下操作而并不影响其质量。
据上,本发明又一目的为提供一种由前述积层板所制得的印刷电路板,其具有低介电损耗及高耐热性(例如:高玻璃转化温度)等特性,且适用于高速度高频率讯号传输。其中,该电路板包含至少一个前述积层板,且该电路板可由习知制程制作而成。
【附图说明】
图1为产物化合物B,由DSC仪器量测的焓(enthalpy)变化图,其中X轴为温度(Temperature,单位℃),Y轴为热流量(Heat Flow,单位W/g)。
图2为产物化合物B,由DSC仪器量测Tg的结果图,其中X轴为温度(Temperature,单位℃),Y轴为热流量(Heat Flow,单位W/g)。
图3为反应前驱物化合物A的FTIR图,其中X轴为波数(wavenumber,单位cm-1),Y轴为穿透度(Transmittance,单位T%)。
图4为产物化合物B的FTIR图,其中X轴为波数(wavenumber,单位cm-1),Y轴为穿透度(Transmittance,单位T%)。
【具体实施方式】
为进一步揭露本发明,以使本发明所属技术领域者具有通常知识者可了解本发明的目的、特征及功效并据以实施本发明,以下谨以数个实施例并配合所附的图式,进一步说明本发明。然应注意者,以下实施例仅用以对本发明做进一步的说明,并非用以限制本发明实施范围,且任何本发明所属技术领域者具有通常知识者在不违背本发明的精神下所得以达成的修饰及变化,均属于本发明的范围。
制造例:
架设反应容器3升,其配备有回流冷凝器、温度计、及搅拌装置,将134.0克(1mol)对苯二醛、218克(2mol)4-氨基酚、205.7克丙二醇单甲基醚和178.0克甲苯加入共混,搅拌加热后,紧接着4小时回流脱水,在约115至125℃,冷却到室温,得到聚甲亚胺(polyazomethine)化合物(化合物A)。于3升玻璃夹套的反应器中加入388g化合物A,再加入172克的甲醛、242ml二甲苯和484ml丁醇。将反应混合物加热至80℃至82℃并持续搅拌混合。最后加入238克苯胺,加热至90至95℃,回流反应6小时。最后反应混合物中加入另外600ml二甲苯和1200ml丁醇,以使反应温度降至常温,将醇溶剂移除,获得固体含量(solids content)约70%的改性苯并噁嗪化合物产物(在下文中简称改性Bz或化合物B)。
制造例的产物的特性测试数据如图3及图4的FTIR图。
图3为反应前驱物化合物A的FTIR图、图4为产物化合物B的FTIR图,图4显示反应后产生苯并噁嗪的特征峰1599(cm-1)、1493(cm-1),而图3并无这两个苯并噁嗪的特征峰,显示化合物B已合成完成改性苯并噁嗪。图3及图4的特征峰1600至1700(cm-1)则显示了-C=N-官能基的特征峰。
实施例树脂组合物的组成分别列于表1中。
实施例
按照表1列出的配方把相关成分充分混合,得到树脂组合物的树脂清漆,其中E1至E8表示本发明的树脂组合物的实施例,C1至C2表示前述树脂组合物的比较例。应注意的是,尽管本发明为彰显某些组份或用量的功效,而将组合物区分为实施例和比较例,但此区分只是为了便利说明,并不代表比较例不属于本发明的一部分。
下列实施例和比较例中使用的化学品名如下:
LZ 8280:双酚F型苯并噁嗪树脂(BPF-Bz),购自Huntsman;
LZ 8290:双酚A型苯并噁嗪树脂(BPA-Bz),购自Huntsman;
LZ 8270:酚酞型苯并噁嗪树脂(酚酞-Bz),购自Huntsman;
BNE-200:双酚A酚醛环氧树脂,购自长春人造树脂;
HP-7200H:二环戊二烯环氧树脂,购自大日本油墨化学;
PNE-177:苯酚酚醛型环氧树脂,购自长春人造树脂;
EF-40:苯乙烯马来酸酐共聚物,购自Cray Valley公司;
DDS:二氨基二苯砜,购自Atul LTD公司;
HPC-8000:聚酯,购自大日本油墨化学;
LA-7054:三氮杂苯酚醛树脂(ATN),购自大日本油墨化学;
PN:苯酚酚醛树脂,购自Kolon;
BA-230S:双酚A氰酸酯树脂,购自Lonza公司;
Homide125:双马来酰亚胺,购自HOS-Technik公司;
SPB-100:磷腈化合物,购自大冢化学;
SAYTEX 8010:十溴二苯乙烷,购自Albemarle公司;
XZ92741:DOPO酚醛阻燃剂,购自陶氏化学;
2E4MZ:2-乙基-4-甲基咪唑,购自四国化成;
525:二氧化硅,购自硅比科。
基板制备及分析
将上述实施例及比较例树脂组合物分别于搅拌槽中混合均匀后,分别置入浸渍槽中,再将玻璃纤维布(2116E-玻璃纤维布(E-Glass Fabric),购自南亚塑料工业)于浸渍槽中浸渍,使树脂组合物附着于玻璃纤维布,再进行加热烘烤成半固化态而得半固化片。
将上述分别制得的半固化片分别取四张,及两张18μm铜箔,依铜箔、四片半固化片、铜箔的顺序进行迭合,再于真空条件下经由210℃压合2小时形成铜箔基板,其中四片半固化片固化形成两铜箔间的绝缘层。
分别将上述含铜箔基板及铜箔蚀刻后的不含铜基板进行物性测定,其中包括不含铜箔的四片半固化片压合后的基板,其树脂含量(resin content)约55%,除了介电常数及介电损耗以两片半固化片制作的不含铜箔测定外,其余不含铜箔物性皆为四片半固化片制作的不含铜基板所测定,物性测定项目包含:玻璃转化温度(Tg,DSC仪器量测,依IPC-TM-650 2.4.24.4所述方法测量)、耐热性(T288,TMA热机械分析仪器测量:摄氏288度下,测量含铜基板受热不爆板的时间,依IPC-TM-650 2.4.24.1所述方法测量)、介电常数(dielectric constant,Dk,AET微波诱电分析仪量测,依JIS C2565所述方法测量,于10GHz频率下量测,Dk值越低介电特性越佳,Dk值差异0.1即为本领域明显差异)、介电损耗(dissipationfactor,Df,AET微波诱电分析仪量测,依JIS C2565所述方法测量,于10GHz频率下量测,Df值越低介电特性越佳,Df值差异0.001即为本领域明显差异)、阻燃性(依UL94规范方法量测,其中等级排列V-0较V-1佳、V-1较V-2佳)。测试结果分别列于表2。
由表1及表2,参见E1至E2及C1至C2可发现含有改性Bz的树脂组合物所制造而得的基板有明显较高的玻璃转化温度(Tg),且介电损耗(Df)明显优于(低于)添加BPF-Bz及BPA-Bz的树脂组合物。
E3至E5为使用不同共硬化剂种类或添加不同数量等参数变化对于基板特性的影响;由E6得知将改性Bz与其他种类Bz混用亦可达到良好的基板综合特性,如较高的玻璃转化温度(Tg)以及良好的介电损耗(Df);此外,由E7及E8可观察到藉由阻燃剂的添加可达到良好的V-0等级阻燃效果,综合上述改性Bz可搭配其他各种不同成分与用量来调整基板各种性质的变化而满足实际使用上的需求。
综合实施例及比较例可发现,C1及C2分别使用一般BPA型苯并噁嗪化合物及BPF型苯并噁嗪化合物,基板具有较差(较低)的玻璃转化温度及较差(较高)的介电损耗,C3使用酚酞型苯并噁嗪化合物,基板虽能达到较高的玻璃转化温度但介电损耗极差。由比较结果显示,使用本发明改性苯并噁嗪化合物所制成的基板能同时兼具较佳(较高)的玻璃转化温度及较佳(较低)的介电损耗。
如上所述,本发明的树脂组合物,其借着包含特定的组成份及比例,以使可达到低介电常数、低介电损耗、高耐热性及高阻燃性。该树脂组合物可制备用于制造积层板(铜箔基板)及印刷电路板的半固化片或树脂膜。就产业上的可利用性而言,利用本发明所衍生的产品,当可充分满足目前市场的需求。
本发明在上文中已以较佳实施例揭露,然熟习本项技术者应理解的是,该实施例仅用于描绘本发明,而不应解读为限制本发明的范围。应注意的是,举凡与该实施例等效的变化与置换,均应设为涵盖于本发明的范畴内。因此,本发明的保护范围当以下文的专利申请范围所界定者为准。
Claims (10)
1.一种改性苯并噁嗪化合物,其具有以下式(1)或式(2)所示结构:
其中,
R为脂肪族烃基或芳香基;
R’选自由亚氨基、烯丙基、C1至C20脂肪族烃基、二环戊二烯基、及芳香基所组成的群组;
A选自由-CH2-、-CH(CH3)-、及-C(CH3)2-所组成的群组,且各A相同或不同;
B为亚芳基;
m为0至4;
n为0至1;及
a1、a2、a3及b各自分别为0或1。
2.如权利要求1所述的改性苯并噁嗪化合物,其选自由式(6)、式(7)、式(8)、式(9)、及式(10)所示的化合物所组成的群组:
3.一种制造改性苯并噁嗪化合物的方法,其包含:将苯二醛化合物与氨基酚化合物于溶剂中反应形成甲亚胺基酚化合物,再由该甲亚胺基酚与伯胺及甲醛反应。
4.如权利要求3所述的方法,其中,该苯二醛化合物为式(3)所示的化合物:
其中,
R为脂肪族烃基或芳香基;
A选自由-CH2-、-CH(CH3)-、及-C(CH3)2-所组成的群组,且各个A相同或不同;
B为亚芳基;
m为0至4;及
a1、a2、a3及b各自分别为0或1。
5.如权利要求3所述的方法,其中该氨基酚化合物为式(4)或(5)所示的化合物:
其中,
R各自独立为氢、脂肪族烃基、或芳香基;
A选自-CH2-、-CH(CH3)-、-C(CH3)2-、脂肪族亚烃基、及亚芳基所组成的群组;及
n为0或1。
6.如权利要求3所述的方法,其中,该伯胺为具有通式R’N H2的伯胺,其中,R’选自亚氨基、烯丙基、C1至C20脂肪族烃基、二环戊二烯基、及芳香基所组成的群组。
7.一种树脂组合物,其包含:(A)如权利要求1或2所述的改性苯并噁嗪化合物或其预聚物或两者的混合物;及(B)交联剂。
8.如权利要求7所述的树脂组合物,其中(B)交联剂选自由下列所组成的群组:环氧树脂、氰酸酯树脂、异氰酸酯、聚苯醚树脂、马来酰亚胺、聚酰胺、聚酰亚胺、酚氧树脂、苯乙烯马来酸酐共聚物、聚酯、烯烃聚合物、酚树脂、胺类硬化剂、酸酐硬化剂、二烯丙基双酚A、及其组合。
9.如权利要求7所述的树脂组合物,其进一步包含由下列所组成的群组的性质调整剂:阻燃剂、硬化促进剂、无机填料、表面活性剂、溶剂、及增韧剂。
10.一种如权利要求7至9中任一项所述的树脂组合物所制成的制品,其中,该制品为树脂膜、半固化片、积层板或印刷电路板。
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CN110204857A (zh) * | 2019-06-06 | 2019-09-06 | 江门建滔积层板有限公司 | 一种基于苯并噁嗪树脂的低介电覆铜板的制备方法 |
CN112059103A (zh) * | 2020-08-31 | 2020-12-11 | 安徽省含山县威建铸造厂(普通合伙) | 一种铸造用酸法冷芯盒树脂的制备方法及其应用 |
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CN106700548B (zh) | 2016-12-30 | 2019-04-30 | 广东生益科技股份有限公司 | 一种含有苯并噁嗪树脂组合物的制备方法及由其制成的预浸料和层压板 |
KR102134377B1 (ko) | 2017-09-15 | 2020-07-15 | 주식회사 엘지화학 | 감광성 수지 조성물 및 이를 포함한 경화막 |
JP6515255B1 (ja) * | 2017-10-20 | 2019-05-15 | 日本化薬株式会社 | 硬化性樹脂組成物、ワニス、プリプレグ、硬化物、及び、積層板または銅張積層板 |
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