CN102516248B - 含有斜线型萘二酰亚胺单元的n-型有机半导体材料 - Google Patents
含有斜线型萘二酰亚胺单元的n-型有机半导体材料 Download PDFInfo
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Abstract
本发明提供了含斜线型芳香萘二酰亚胺单元的n-型有机半导体材料,该材料可以用于有机薄膜场效应晶体管。该材料通过改变以往直线型萘二亚胺分子的将羧酸亚胺六元环接在萘环的1,8位和4,5的特点,改为接在萘环上的1,2位和5,6位,形成五元环和斜线型,可改变材料分子的电荷分布和电子能级。该结构有利于在萘环的3,7位引入可聚合基团从而合成含斜线型芳香萘二酰亚胺单元的聚合物。
Description
技术领域
本发明涉及一种用于有机薄膜场效应晶体管的n-型半导体材料,特别是含有斜线型萘环二酰亚胺单元的有机小分子n-型半导体材料。
背景技术
场效应晶体管(FieldEffectTransistor,FET)是利用电场来控制固体材料导电性能的有源器件,已成为微电子行业中的重要元件之一。目前无机场效应晶体管已经接近小型化的自然极限,而且成本较高,不利于制备大表面积器件。而有机场效应晶体管(OFET)所具有的特点,刚好可以克服上述的不足:材料来源广,可制作成柔性器件,可制成大面积的器件,适合低温加工,可溶液加工成膜,适合大批量生产和低成本的制作工艺等。由于其具有轻、薄、可弯曲折叠等特点,可做成时尚有机电子产品,因此近年来它已经成为有机光电子学中的一个研究热点。
在OFET的应用中有p型和n型半导体材料,他们的具有一样的重要性。但是跟p型有机半导体材料相比,目前n型有机半导体材料的种类少,特别是缺少具有高电子迁移率、空气稳定、可溶液加工性质的n型有机半导体材料。因此为了使OTFT在柔性电子器件及相关产品得到更好的应用,有必要设计并合成新型高电子迁移率、空气稳定的n型有机半导体材料。2000年起,H.E.Katz等人报道了基于萘二酰亚胺单元的空气中稳定的有机n型半导体材料,其迁移率达到0.1cm2/(V.s),(Nature,2000,404,478-481)引起了国际同行的广泛关注与跟踪。近几年,国内外也有很多相关的报道,主要集中于苝二酰亚胺、苯二酰亚胺、萘二酰亚胺以及蒽二酰亚胺等此类多芳香稠环的二酰亚胺分子单元。目前对于多芳香稠环的二酰亚胺类的有机半导体材料的研究中还都是基于直线型芳香环的二酰亚胺单元的一些衍生物。
发明内容
本发明的目的在于提供一种新型含有斜线型芳香萘二酰亚胺单元的n-型有机半导体材料的制备方法,及其在OFET中的应用。该材料通过改变以往直线型萘二亚胺分子的将羧酸亚胺六元环接在萘环的1,8位和4,5的特点,改为接在萘环上的1,2位和5,6位,将其变为五元环和斜线型,可改变材料分子的电荷分布和电子能级,该结构有利于在萘环的3,7位引入可聚合基团从而合成含斜线型芳香萘二酰亚胺单元的聚合物。
本发明的目的在于提供一种新型有机n型半导体材料,其结构如下:
本发明采用如下方法来制备含斜线型芳香萘二酰亚胺的半导体材料:
1.1,2,5,6-萘四羧酸的制备
根据文献方法(J.Org.Chem.1961,26,2522)可制备出1,5-二氰基-2,6-二甲基萘,使用K2Cr2O7在高温高压下使其氧化成羧酸。
2.1,2,5,6-萘四甲酸酐的制备
使用醋酸酐,在回流的条件下将羧酸所合成酸酐。
3.斜线型芳香萘二酰亚胺分子的合成
以醋酸锌为催化剂,萘四甲酸酐与相应的胺反应,使之酰胺化得到目标化合物。
附图说明
图1是以制备例4所得化合物为活性层的FET器件的输出特征曲线(a)和转移特征曲线(b);
图2是以制备例5所得化合物为活性层的FET器件的输出特征曲线(a)和转移特征曲线(b)。
具体实施方式
在下文中,所列实例目的是为更详细的解释本发明,本发明所含内容并不仅限于此。
制备例1:1,2,5,6-萘四甲酸
在70mL的聚四氟乙烯反应釜内衬中加入0.85g1,5-二氰基-2,6-二甲基萘和20mL含有K2Cr2O7(3.56g)和NaOH(0.33g)的水溶液。混合液搅拌半小时后密封在不锈钢的罐子里,加热到220℃并维持10小时。冷却后,过滤,滤液用乙醚处理,取水层加入浓盐酸酸化后,得到黄色固体(1.06g,产率85%)。制备例2:1,2,5,6-萘四甲酸酐
1.0g上步得到的1,2,5,6-萘四羧酸加入到50mL醋酸酐中,在100mL的圆底烧瓶中搅拌回流3小时,减压蒸馏去掉大部分溶剂,真空抽滤,滤渣用甲醇洗,得到0.79g产品,产率90%。
制备例3:N,N’-双(4-(三氟甲基)苯基)-萘-1,2,5,6-双(二甲酰胺)
将上步反应中得到的酸酐(0.586g,2.2mmol)和过量的4-三氟甲基苄胺(6.6mmol)以及醋酸锌(1.54mmol)加入到25mL圆底烧瓶中,加入6mL喹啉,加热至200℃以上,该温度下搅拌反应3小时。冷却后真空抽滤,并依次用热的稀Na2CO3溶液,水,甲苯,甲醇洗。得到1.06g粗产物,产率83%。产物的进一步提存使用真空升华的方法提纯。Elementalanalysis:calcdforC,61.86;H,2.77;N,4.81;found:C,62.03;H,2.77,N,4.87.Mp317-318℃.MALDI-TOF/MS,m/zcalcdforC30H16F6N2O4:582.1,found:582.1;1HNMR(400MHz,CDCl3,ppm):δ=4.97(s,4H),7.60(s,8H),8.12(d,J=8.4Hz,2H),9.35(d,J=8.4Hz,2H).
制备例4:N,N’-双(4-(三氟甲基)苯乙基)-1,2,5,6-萘四甲酰基二酰亚胺
将制备例2中得到的酸酐(0.38g,1.4mmol)和过量的4-三氟甲基苯基乙胺(6.3mmol)以及醋酸锌(1.14mmol)加入到25mL圆底烧瓶中,加入6mL喹啉,加热至200℃以上,该温度下搅拌反应3小时。冷却后真空抽滤,并依次用热的稀Na2CO3溶液,水,甲苯,甲醇洗。得到0.46g粗产物,产率54%。产物的进一步提存使用真空升华的方法提纯。Elementalanalysis:calcdforC,62.96;H,3.30;N,4.59;found:C,63.00;H,3.59,N,4.59.Mp309-310℃.MALDI-TOF/MS,m/zcalcdforC32H20F6N2O4:610.5,found:610.2;1HNMR(400MHz,CDCl3,ppm):1HNMR(400MHz,CDCl3)δ=9.32(d,J=8.4Hz,2H),8.10(d,J=8.4Hz,2H),7.55(d,J=8.0Hz,4H),7.40(d,J=8.0Hz,4H),4.03(t,J=7.6Hz,4H),3.12(t,J=7.6Hz,4H).
制备例5:N,N’-双(全氟苯乙基)-1,2,5,6-萘四甲酰基二酰亚胺
将制备例2中得到的酸酐(0.38g,1.4mmol)和过量的全氟苯基乙胺(5.68mmol)以及醋酸锌(0.96mmol)加入到25mL圆底烧瓶中,加入6mL喹啉,加热至200℃以上,该温度下搅拌反应3小时。冷却后真空抽滤,并依次用热的稀Na2CO3溶液,水,甲苯,甲醇洗。得到0.47g粗产物,产率51%。产物的进一步提存使用真空升华的方法提纯。Elementalanalysis:calcdforC,55.06;H,1.85;N,4.28;found:C,55.34;H,2.07,N,4.46.Mp307-308℃.MALDI-TOF/MS,m/zcalcdforC30H12F10N2O4:654.06,found:654.0;1HNMR(400MHz,CDCl3,ppm):δ=9.31(s,2H),8.11(s,2H),4.04(s,4H),3.17(s,4H).
制备例6:N,N’-双(1H,1H,2H,2H,3H,3H-全氟正十一烷基)-1,2,5,6-萘四甲酰基二酰亚胺
将制备例2中得到的酸酐(0.20g,0.7mmol)和过量的C8F17(CH2)3NH2(1.06g,2.1mmol)以及醋酸锌(0.57mmol)加入到25mL圆底烧瓶中,加入6mL喹啉,加热至200℃以上,该温度下搅拌反应3小时。冷却后真空抽滤,并依次用热的稀Na2CO3溶液,水,甲苯,甲醇洗。得到0.57g粗产物,产率68%。产物的进一步提存使用真空升华的方法提纯。Elementalanalysis:calcdforC,36.44;H,1.36,N,2.36;found:C,36.74;H,1.44,N,2.36.Mp238-239℃.MALDI-TOF/MS,m/zcalcdforC30H12F26N2O4:1186.06,found:1186.1.
制造FET装置
实施例
本实施例FET装置采用底栅顶接触结构,以热氧化生长出300nm的SiO2作为绝缘层的单晶硅片基底为栅电极。再依次在上面制作活性层和源漏电极。首先,将硅片基底依次在浓硫酸溶液(3H2SO4∶1H2O2)、蒸馏水、丙酮、异丙醇中清洗并烘干。然后通过真空热蒸镀的方法在基底上镀上45nm厚的活性层和60nm厚的金电极。所得器件的沟道宽度和长度分别是6mm和300μm。
实施例的器件电学性能评估在半导体表征体系(Agilent4155C)中进行,电子迁移率通过电流传输曲线计算,具体的,通过下列在饱和区的电流方程式得到:(Id)sad=(W/2L)μCi(Vg-Vt)2,通过(Id)sad 1/2对Vg作图,从斜率求的迁移率。其中(Id)sad饱和区的源-漏电流。W和L是沟道宽度和长度,Ci(Ci=10nF)是绝缘层的电容量,Vg和Vt分别是栅电压和阈电压。
图1是以制备例4所得化合物为活性层的FET器件的输出特征曲线(a)和转移特征曲线(b)。图2是以制备例5所得化合物为活性层的FET器件的输出特征曲线(a)和转移特征曲线(b)。表1为分别以制备例4和5为活性层所制备的FET器件的各种参数归纳。
表1
活性层 | 迁移率(cm2/(Vs))1 | 阈电压(V) | 开关比 | 器件个数 |
制备例4 | 0.011(0.0074) | 12-45 | 104 | 11 |
制备例5 | 0.024(0.015) | 9-40 | 105 | 12 |
1:迁移率最大值,括号内为平均值。
Claims (3)
1.一种含斜线型芳香萘环的二酰亚胺单元的n-型有机半导体材料,其特征在于:该材料具有以下结构通式,其中R1选自C1-C28烷基、C1-C28氟化烷基、C1-C28环烷基、C1-C28氟化环烷基、C1-C20芳香基、C1-C20氟化芳香基、被含有20个碳以下烷基取代的苯基、被含有20个碳以下氟化烷基取代的苯基,
2.一种如权利要求1所述的n-型有机半导体材料的制备方法,该方法具有以下的合成路线:
3.一种如权利要求1所述的n-型有机半导体材料的用途,其特征在于:该材料用于有机薄膜场效应晶体管。
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