CN1254710A - 聚苯并噁唑树脂及其前体 - Google Patents
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Abstract
本发明提供了一种用于半导体用途的热特性、电特性、物理特性及机械特性优良的耐热性树脂。即,本发明提供了以通式(A)表示的聚苯并噁唑前体、以及以通式(D)表示的聚苯并噁唑树脂。式(A)、(D)中,n表示2~1000的整数,X表示选自式(B)的结构。式(B)中,Y表示选自式(C)的结构,该结构中苯环上的氢原子也可用由甲基、乙基、丙基、异丙基、丁基、异丁基、叔丁基、氟原子、以及三氟甲基组成的组中选择的至少1个基团取代。
Description
本发明涉及热特性、电特性、机械特性、物理特性优良的聚苯并噁唑树脂,可适用于作为半导体用的层间绝缘膜、保护膜、多层电路的层间绝缘膜、挠性镀铜板的覆盖涂层、焊料保护膜、液晶取向膜等。
历来,作为半导体用的层间绝缘膜,均使用以化学气相法等制作的二氧化硅等无机绝缘膜。但是,二氧化硅等无机绝缘膜的介电常数高,为了高速化、高性能化,正在研究适用的有机材料作为绝缘膜。并使用了耐热性、电特性、机械特性等优良的聚酰亚胺树脂作为半导体用途的有机材料。近年来,随着半导体的高机能化、高性能化,更加要求显著改善耐热性、电特性、吸湿性、热膨胀系数等,因此,有必要研究更高性能的树脂。
出于这样的情况,试验着将在吸水性、电特性方面比聚酰亚胺树脂显示出更优良性能的聚苯并噁唑树脂用于半导体用途的绝缘材料。聚苯并噁唑树脂要是仅仅满足热特性、电特性、机械特性、特理特性的任何一项是容易的,例如,由4,4’-二氨基-3,3-二羟基联苯和对苯二甲酸构成的聚苯并噁唑树脂,具有非常优良的耐热分解性、高Tg等耐热性,但另一方面,介电常数、介质损耗角正切等电特性则不怎么好。另外,由2,2’-双(3-氨基-4-羟基苯基)六氟丙烷和对苯二甲酸构成的聚苯并噁唑树脂虽显示出低介电常数等良好的电特性,但是耐热性、物理特性等却不怎么好。这样,现状就是还没有得到热特性、电特性、机械特性及物理特性全部优良的树脂。
本发明的目的在于,提供一种在半导体用途方面热特性、电特性、物理特性及机械特性均优良的耐热性树脂。
本发明人鉴于上述的过去存在的问题,进行了反复的深入研究,结果发现了以通式(A)表示的聚苯并噁唑前体及用通式(D)表示的聚苯并噁唑树脂,从而完成了本发明。(式(A),(D)中,n表示2~1000的整数,X表示选自式(B)的结构)(式(B)中,Y表示选自式(C)的结构,在该结构中苯环上的氢原子也可以用由甲基、乙基、丙基、异丙基、丁基、异丁基、叔丁基、氟原子、以及三氟甲基组成的组中选择的至少1个基团取代。)
本发明的聚苯并噁唑前体,可以由具有上述式(B)的任何一种结构的双氨基酚化合物和2,2’-双(三氟甲基)-4,4’-联苯撑二羧酸,通过向来的酰氯法、活化酯法、在多磷酸或二环己基碳化二亚胺等脱水缩合剂存在下的缩合反应等方法获得。
作为本发明中所使用的具有式(B)任何一种结构的双氨基酚化合物的代表例,可举出:2,4-二氨基间苯二酚、4,6-二氨基间苯二酚、2,2’-双(3-氨基-4-羟基苯基)六氟丙烷、2,2’-双(4-氨基-3-羟基苯基)六氟丙烷、2,2’-双(3-氨基-4-羟基苯基)丙烷、2,2’-双(4-氨基-3-羟基苯基)丙烷、3,3’-二氨基-4,4’-二羟基二苯基砜、4,4’-二氨基-3,3’-二羟基二苯基砜、3,3’-二氨基-4,4’-二羟基联苯、4,4’-二氨基-3,3’-二羟基联苯、3,3’-二氨基-4,4’-二羟基二苯基醚、4,4’-二氨基-3,3’-二羟基二苯基醚、2,2’-双(3-氨基-4-羟基-2-三氟甲基)丙烷、2,2’-双(4-氨基-3-羟基-2-三氟甲基)丙烷、2,2’-双(3-氨基-4-羟基-5-三氟甲基)丙烷、2,2’-双(4-氨基-3-羟基-5-三氟甲基)丙烷、2,2’-双(3-氨基-4-羟基-6-三氟甲基)丙烷、2,2’-双(4-氨基-3-羟基-6-三氟甲基)丙烷、2,2’-双(3-氨基-4-羟基-2-三氟甲基)六氟丙烷。2,2’-双(4-氨基-3-羟基-2-三氟甲基)六氟丙烷、2,2’-双(3-氨基-4-羟基-5-三氟甲基)六氟丙烷、2,2’-双(4-氨基-3-羟基-5-三氟甲基)六氟丙烷、2,2’-双(3-氨基-4-羟基-6-三氟甲基)六氟丙烷、2,2’-双(4-氨基-3-羟基-6-三氟甲基)六氟丙烷、3,3’-二氨基-4,4’-二羟基-2,2’-三氟甲基联苯、4,4’-二氨基-3,3’-二羟基-2,2’-三氟甲基联苯、3,3’-二氨基-4,4’-二羟基-5,5’-三氟甲基联苯、4,4’-二氨基-3,3’-二羟基-5,5’-三氟甲基联苯、3,3’-二氨基-4,4’-二羟基-6,6’三氟甲基联苯、4,4’-二氨基-3,3’-二羟基-6,6’-三氟甲基联苯等。
在本发明的聚苯并噁唑前体的制造方法中,例如采用酰氯法,首先,所使用的酸氯化物,即2,2’-双(三氟甲基)-4,4’-联苯撑二羧酰氯,可以通过在N,N-二甲基甲酰胺等催化剂存在下,使2,2’-双(三氟甲基)-4,4’-联苯撑二羧酸由室温到75℃与过剩量的二氯亚砜反应,再经加热及减压将过剩的二氯亚砜蒸去,然后将残渣用己烷等溶剂重结晶而得到。接着,将双氨基酚化合物溶解在通常的N-甲基-2-吡咯烷酮、N,N-二甲基乙酰胺等极性溶剂中;在吡啶等酸接受剂存在下,与2,2’-双(三氟甲基)-4,4’-联苯撑二羧酰氯在室温到-30℃下反应,籍此可得到聚苯并噁唑前体。
本发明的聚苯并噁唑树脂,可以通过将这样得到的聚苯并噁唑前体,按以往的方法,经加热或用脱水剂处理使之进行缩合反应而得到。可按要求在该树脂中添加表面活性剂或偶合剂等各种添加剂,即可用作半导体用层间绝缘膜、保护膜、多层电路的层间绝缘膜、挠性镀铜板的覆盖涂层、焊料保护膜、液晶取向膜等。
此外,本发明的聚苯并噁唑树脂的前体,经过与作为感光剂的萘醌二迭氮化合物一起使用,可以作为感光性树脂组合物使用。
本发明的聚苯并噁唑前体,通常将其溶解在溶剂中,制成漆状使用为佳。作为溶剂,可以使用N-甲基-2-吡咯烷酮、γ-丁内酯、N,N-二甲基乙酰胺、二甲基亚砜、二甘醇二甲基醚、二甘醇二乙基醚、二甘醇二丁基醚、丙二醇一甲基醚、一缩二丙二醇一甲基醚、丙二醇一甲基醚乙酸酯、乳酸甲酯、乳酸乙酯、乳酸丁酯、甲基-1,3-丁二醇乙酸酯、1,3-丁二醇-3-一甲基醚、丙酮酸甲酯、丙酮酸乙酯、3-甲氧基丙酸甲酯等的1种,或者2种以上混合使用。
在使用本发明的聚苯并噁唑前体时,首先将该前体及其它化合物溶解在上述溶剂中,再涂布在适当的支持体,例如硅晶片或陶瓷基盘等之上。涂布方法可采用使用旋转器的回转涂布、使用喷雾器的喷雾涂布、浸渍、印刷、辊涂等。这样形成涂膜后,进行加热处理,转变成聚苯并噁唑后使用为佳。
以下通过实施例具体说明本发明,但本发明丝毫不受实施例内容的限定。以下的份数表示重量份数。
实施例1
将2,2’-双(3-氨基-4-羟基苯基)六氟丙烷73.2份(0.2mol)溶解在干燥的二甲基乙酰胺200份中,添加吡啶39.6份(0.5mol),然后在干燥氮气下,于-15℃将2,2’-双(三氟甲基)-4,4’-联苯撑二羧酰氯83.0份(0.2mol)溶解在环己烷100份中的溶液用30分钟滴加。滴加终了后,返回到室温,在室温下搅拌5小时。然后将反应液滴加到蒸馏水7升中,收集沉淀物并进行干燥,得到聚苯并噁唑前体(通式(E))。此处使用东ソ-株式会社制GPC经聚苯乙烯换算,求出所得的聚苯并噁唑前体的数均分子量(Mn),为44000。
将该聚苯并噁唑前体溶解在N-甲基-2-吡咯烷酮中,用0.2μm的特氟隆过滤器进行过滤,得到漆状物。
将该漆状物用刮刀涂布在玻璃板上。然后,在烘箱中于70℃干燥1小时,剥离后得到膜厚20μm的聚苯并噁唑前体薄膜。将该薄膜用金属框固定,以150℃/30分、250℃/30分、350℃/30分的顺序加热,得到聚苯并噁唑树脂(通式(F))。
使用该树脂薄膜,评价各种特性,将其结果汇总于表1。
实施例2
使用4,4’-二氨基-3,3’-二羟基联苯43.2份(0.2mol)代替实施例1的2,2’-双(3-氨基-4-羟基苯基)六氟丙烷73.2份(0.2mol),与实施例1同样制作聚苯并噁唑树脂(通式(G)),进行评价。使用东ソ-株式会社制GPC经聚苯乙烯换算,求出这样所得的聚苯并噁唑树脂的数均分子量(Mn),为34000。
实施例3
使用2,2’-双(3-氨基-4-羟基苯基)丙烷51.6份(0.2mol)代替实施例1的2,2’-双(3-氨基-4-羟基苯基)六氟丙烷73.2份(0.2mol),与实施例1同样制作聚苯并噁唑树脂(通式(H)),进行评价。使用东ソ-株式会社制GPC经聚苯乙烯换算,求出这样所得到的聚苯并噁唑树脂的数均分子量(Mn),为54000。
使用3,3’-二氨基-4,4’-二羟基二苯基砜56.1份(0.2mol)代替实施例1的2,2’-双(3-氨基-4-羟基苯基)六氟丙烷73.2份(0.2mol),与实施例1同样制作聚苯并噁唑树脂(通式(I)),进行评价。用东ソ-株式会社制GPC经聚苯乙烯换算,求出所得聚苯并噁唑树脂的数均分子量(Mn),为41000。
实施例5
使用3,3’-二氨基4,4’-二羟基二苯基醚46.4份(0.2mol)代替实施例1的2,2’-双(3-氨基-4-羟基苯基)六氟丙烷73.2份(0.2mol),与实施例1同样制作聚苯并噁唑树脂(通式(J)),进行评价。使用东ソ-株式会社制GPC经聚苯乙烯换算,求出这样得到的聚苯并噁唑树脂的数均分子量(Mn),为52000
比较例1
使用间苯二甲酰氯40.6份(0.2mol)代替实施例1的2,2’-双(三氟甲基)-4,4’-联苯撑二羧酰氯83.0份(0.2mol),与实施例1同样制作聚苯并噁唑树脂(通式(K)),进行评价。使用东ソ-株式会社制GPC经聚苯乙烯换算,求出这样得到的聚苯并噁唑树脂的数均分子量(Mn),为44000。
比较例2
使用4,4’-联苯撑二羧酰氯46.2份(0.2mol)代替实施例1的2,2’-双(三氟甲基)-4,4’-联苯撑二羧酰氯83.0份(0.2mol),与实施例1同样制作聚苯并噁唑树脂(通式(L)),进行评价。使用东ソ-株式会社制GPC经聚苯乙烯换算,求出这样得到的聚苯并噁唑树脂的数均分子量(Mn),为49000。将实施例和比较例中的评价结果示于表1。
表1
介电常数 | 耐热性(℃) | CTE(x10-6) | 吸水率(%) | |
实施例1实施例2实施例3实施例4实施例5 | 2.52.92.72.82.8 | 511522515518514 | 4210414041 | 0.10.20.10.20.1 |
比较例1比较例2 | 2.82.9 | 505512 | 5145 | 0.20.2 |
介电常数:按照JIS-K6911标准,以频率1MHz,使用Hewlatt-Packard Co.制HP-4284A Precision LCR仪进行测定。
耐热性:使用精工电子工业(株)制TG/DTA 220,在氮气流下,以升温速度10℃/分测定重量减少5%的温度。
CTE:使用精工电子工业(株)制TMA/SS 120C,以升温速度5℃/分,在25-100℃的温度范围内,测定热膨胀率。
吸水率:用重量法测定温度85℃、湿度85%、24小时后的吸水率。
如由表1所能看出的那样,本发明的聚苯并噁唑树脂显示出优良的热特性、电特性、机械特性及物理特性。因此,可适用作为半导体用的层间绝缘膜、保护膜、多层电路的层间绝缘膜、挠性镀铜板的覆盖涂层、焊料保护膜、液晶取向膜等。
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CN (1) | CN1215049C (zh) |
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CN106459403A (zh) * | 2014-05-28 | 2017-02-22 | 味之素株式会社 | 聚醚酮化合物 |
CN107474251A (zh) * | 2017-08-18 | 2017-12-15 | 南京工业大学 | 一种膜电容器复合介电薄膜的制备方法 |
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JP2004107621A (ja) * | 2002-07-25 | 2004-04-08 | Polymatech Co Ltd | ポリベンザゾール前駆体フィルム、ポリベンザゾールフィルム及びそれらの製造方法 |
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
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CN101215472B (zh) * | 2008-01-15 | 2010-06-02 | 东华大学 | 含氟的芳杂环液晶聚合物及其制备方法 |
CN103682364A (zh) * | 2013-12-27 | 2014-03-26 | 上海孚赛特新材料股份有限公司 | 锂电池负极的胶粘剂及其制备的锂电池负极材料及锂电池 |
CN106459403A (zh) * | 2014-05-28 | 2017-02-22 | 味之素株式会社 | 聚醚酮化合物 |
CN107474251A (zh) * | 2017-08-18 | 2017-12-15 | 南京工业大学 | 一种膜电容器复合介电薄膜的制备方法 |
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EP0990673A3 (en) | 2000-09-20 |
DE69901049D1 (de) | 2002-04-25 |
KR20000023465A (ko) | 2000-04-25 |
EP0990673B1 (en) | 2002-03-20 |
US6204356B1 (en) | 2001-03-20 |
EP0990673A2 (en) | 2000-04-05 |
MY116046A (en) | 2003-10-31 |
SG104255A1 (en) | 2004-06-21 |
TW495524B (en) | 2002-07-21 |
CN1215049C (zh) | 2005-08-17 |
DE69901049T2 (de) | 2002-11-21 |
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