CN114437315A - 新型噻唑桥联异靛蓝类受体及聚合物以及它们的制备方法与应用 - Google Patents
新型噻唑桥联异靛蓝类受体及聚合物以及它们的制备方法与应用 Download PDFInfo
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Abstract
本发明公开一种新型噻唑桥联异靛蓝类受体及聚合物以及它们的制备方法与应用。该聚合物的结构如式I所示,其中,R为C6~C60的直链或支链烷基。本发明还提供式I所示聚合物的制备方法。本发明的原料为商业化产品;合成路线简单;产物构型唯一,产率较高,合成方法具有普适性。以本发明的新型噻唑桥联异靛蓝类聚合物作为有机半导体层来制备有机场效应晶体管,空穴迁移率最高为0.048cm2V‑1s‑1,电子迁移率最高为0.034cm2V‑1s‑1,在有机场效应晶体管的双极性器件中具有良好的应用前景。
Description
技术领域
本发明属于材料领域,具体涉及新型噻唑桥联异靛蓝类受体及聚合物以及它们的制备方法与应用。
背景技术
有机场效应晶体管(Organic field-effect transistors,简称OFETs)的半导体活性层是由具有π共轭结构的有机小分子或者共轭聚合物组成。其工作原理是通过垂直电场来调控材料导电能力的有源器件。与无机半导体材料相比,OFETs具有质量轻可便携、柔性好可折叠、透明度高以及可溶液法加工等优点,在柔性显示背板、传感器阵列以及电子皮肤等方面具有巨大潜力。
共轭聚合物与小分子材料相比,具有成膜性好、柔性可折叠、可大面积加工等优点,受到科研工作者的极大关注。因此,制备高性能的聚合物半导体材料对于本领域发展具有十分重要的意义。根据载流子的传输性质,有机半导体材料可分为p型空穴传输,n型电子传输,双极性材料。但是目前报道的桥联异靛蓝类聚合物材料大部分为p型材料,n型和双极性材料发展相对缓慢。
发明内容
本发明的一个目的是提供一种噻唑桥联异靛蓝(IBTzI)受体及聚合物。
本发明所提供的IBTzI类聚合物,其结构通式如式I所示:
上述式I中,R可为碳原子总数为6-60的直链或支链烷基;
Ar选自如下A类基团中的任意一种;
其中,所述A类基团的结构式如下所示:
式I中,R具体可为碳原子总数为20-50的直链或支链烷基;更具体可为:4-十八烷基二十二烷;
式I中,n表示聚合物,n可为10-110的整数,具体可为25-59的整数,更具体可为59或25。
所述式I所示聚合物具体可为聚合物PIBTzI-BT和PIBTzI-DFBT;
其中,所述聚合物PIBTzI-BT的结构式如式I-a所示:
所述聚合物PIBTzI-DFBT的结构式如式I-b所示:
本发明还提供了式I所示聚合物的制备方法。
上述式I所示聚合物通过包括如下步骤的方法制备得到:
将式IV所示化合物与双锡试剂在催化剂和配体作用下进行聚合反应,得到所述式I所示聚合物;
式IV中,R的定义与前述式I中R的定义相同;
上述方法中,双锡试剂选自如下化合物中的任意一种:
所述催化剂可为三(二亚苄基丙酮)二钯;
所述配体可为三(邻甲基苯基)膦;
所述式IV所示化合物、双锡化合物、催化剂、配体的投料摩尔比依次可为1.00:1.00:(0.03~0.1):(0.24~0.4),具体可为1:1:0.03:0.24。
所述聚合反应中,反应温度可为110~115℃;反应时间可为1小时~120小时;具体可为72小时;
所述聚合反应在有机溶剂中进行,所述有机溶剂具体可为无水甲苯。
所述方法还可包括如下提纯步骤:
在所述聚合反应完毕后,将所得反应体系冷却后依次加入浓盐酸和甲醇,室温下搅拌3小时后过滤,将所得滤饼依次用甲醇、丙酮、正己烷抽提,抽提至无色后,再用三氯甲烷抽提,蒸除溶剂后用甲醇沉降,真空干燥后得到聚合物;
其中,甲醇和浓盐酸的体积比具体可为20:1,浓盐酸的浓度具体可为12M。
此外,上述起始原料式IV所示化合物也属于本发明的保护范围。
式IV中R的定义与本发明所述式I中R的定义相同。
上述式IV所示化合物通过包括如下步骤的方法制备得到:
1a)6-溴-7-氟靛红和RI在碳酸钾的四氢呋喃/N,N-二甲基甲酰胺溶液中加热回流反应,得到式II所示的烷基取代-2-氟靛红(即F-Isatin);
RI、式II中R的定义与式IV中R的定义相同;
1b)将步骤1a)所得式II所示烷基取代-2-氟靛红在水合肼的催化作用下进行还原反应,得到III所示7-氟-1-烷基取代吲哚-2-二酮(即F-indolin-2-one);
式III中R的定义与式IV中R的定义相同;
1c)将步骤1b)所得式III所示的7-氟-1-烷基取代吲哚-2-酮和二醛基-反式联二噻唑在六氢吡啶催化作用下进行反应,得到IV所示噻唑桥联异靛蓝(即IBTzI);
上述方法步骤1a)中,6-溴-7-氟靛红和RI的摩尔比可为:1:1.2-2.5,具体可为1:1.2;
6-溴-7-氟靛红与无水碳酸钾的摩尔比可为1:1.2-1.5,具体可为1:1.5;
所述四氢呋喃和N,N-二甲基甲酰胺的体积比可为1:1;反应步骤中,温度为45-55℃,时间为8~16小时;
步骤1b)中,式II所示烷基取代-2-氟靛红与水合肼的摩尔比可为1:30-50,具体可为1:30;反应步骤中,温度可为105-115℃,时间可为12~24小时;
步骤1c)中,所述7-氟-1-烷基取代吲哚-2-酮和二醛基-反式联二噻唑的投料摩尔用量比可为2.1~2.5:1,具体可为2.13:1;反应步骤中,温度可为60-70℃,时间为3~12小时。
上述方法的合成路线如图1所示。
本发明所提供的式I所示化合物作为双极性聚合物半导体材料在制备有机场效应晶体管器件中的应用也属于本发明的保护范围,所述有机场效应晶体管具体可为双极性场效应晶体管器件。
本发明的另一目的是提供一种有机场效应晶体管器件,所述有机场效应晶体管器件以式I所示化合物为有机半导体活性层。
本发明的优点在于:
1、原料为商业化产品,合成路线简单,单体构型唯一,纯化容易且产率高,同时和聚合物都是新分子,可以推广到各种直链或支链噻唑桥联异靛蓝类聚合物的合成;
2、噻唑桥联异靛蓝类聚合物的LUMO能级较低,有利于电子的注入和传输,可用于制备高性能的双极性场效应晶体管器件;
3.以本发明噻唑桥联异靛蓝类聚合物为半导体层制备的有机场效应晶体管有较高的迁移率(μ)和开关比(空穴迁移率最高为0.048cm2 V-1s-1,电子迁移率最高为0.034cm2V-1s-1,开关比最高为106),在双极性聚合物半导体材料OFETs中有良好的应用前景。
本发明研究了一种通用的方法,合成了新型的噻唑桥联异靛蓝类(bridged-isoindigo,简称IBTzI)受体及聚合物,并研究了其在有机场效应晶体管中的应用。聚合物的HOMO(最高占据分子轨道)和LUMO(最低未占分子轨道)能级较低,紫外可见光谱显示光学带隙小于1.80eV,测试结果表明该类聚合物表现出优异的双极性传输特性。以反式联二噻唑为单元的桥联异靛蓝类受体制备的聚合物扩展了高性能聚合物材料的种类,具有良好的应用和发展前景。
附图说明
图1为本发明提供的制备式IV所示化合物的合成路线图。
图2为聚合物PIBTzI-BT和PIBTzI-DFBT在溶液和薄膜中的紫外可见吸收光谱。
图3为聚合物PIBTzI-BT和PIBTzI-DFBT薄膜的循环伏安曲线图。
图4为以本发明噻唑桥联异靛蓝聚合物为半导体材料的场效应晶体管的结构示意图。
图5为以本发明提供的噻唑桥联异靛蓝聚合物为半导体层的聚合物场效应晶体管的输出特性曲线图和转移特性曲线图(依次为PIBTzI-BT和PIBTzI-DFBT)。
具体实施方式
下面通过具体实施例对本发明进行说明,但本发明并不局限于此,凡在本发明的精神和原则之内所做的任何修改、等同替换和改进等,均应包含在本发明的保护范围之内。
下述实施例中所使用的实验方法如无特殊说明,均为常规方法。
下述实施例中所用的材料、试剂等,如无特殊说明,均可从商业途径得到。
下述实施例中的定量试验,均设置三次重复实验,结果取平均值。
实施例1、聚合物PIBTzI-BT
按照图1所述的合成路线图制备式IV所示化合物。
1a)7-氟-1-烷基取代吲哚-2-二酮(即F-isatin)
将6-溴-7-氟靛红(2.50g,10.29mmol,1.0equiv.),无水碳酸钾(2.23g,16.20mmol,1.5equiv.)和1-碘-4-十八烷基二十二烷(6.37g,30.0mmol,1.2equiv.)加入到干燥的二口瓶中,用氮气置换三次。随后在氮气保护下加入无水四氢呋喃(60mL)和N,N-二甲基甲酰胺(60mL)。混合液升至50℃回流搅拌8小时。冷却至室温后,蒸除溶剂,加入50mL水,再用二氯甲烷萃取(3×100mL),无水硫酸钠干燥,抽滤,蒸除溶剂,过柱。洗脱剂(石油醚:乙酸乙酯=8:1)。最后得到黄色固体(4.21g,59.1%)。
1b)7-氟-1-烷基取代吲哚-2-酮(即F-indolin-2-one)
将7-氟-1-烷基取代吲哚-2-酮(4.0g,4.98mmol,1.0equiv.),加入到干燥的二口瓶中,用氮气置换三次。随后在氮气保护下加入水合肼(15mL,308.63mmol,62.0equiv.)和1,4-二氧六环(15mL)。混合液升至110℃回流搅拌12小时。冷却至室温后,蒸除溶剂,加入20mL水,再用二氯甲烷萃取(3×30mL),无水硫酸钠干燥,抽滤,蒸除溶剂,过柱。洗脱剂(石油醚:乙酸乙酯=8:1)。最后得到黄色固体(2.84g,72.3%)。
1c)噻唑桥联异靛蓝(即IBTzI)
将7-氟-1-烷基取代吲哚-2-酮(516mg,0.65mmol,2.13equiv.)和(2,2'-二噻唑)-5,5'-二醛基(68mg,0.30mmol,1.0equiv.)加入二口瓶中,氮气置换三次后,在氮气保护下加入无水甲醇10.0mL,搅拌溶解后,氮气保护下缓慢滴加六氢吡啶(2.0mL),加热至65℃,回流反应3小时。冷却至室温后,加入少量水洗涤,抽滤,然后再用少量乙醇和二氯甲烷洗涤固体。随后用三氯甲烷重结晶,得到红色固体(357mg,67.2%)。
结构表征数据如下:
核磁:1H NMR(400MHz,Chloroform-d)δ8.36(s,2H),7.73(s,2H),7.23(d,J=3.1Hz,4H),3.92(t,J=7.5Hz,4H),1.69(s,4H),1.39-0.98(m,142H),0.92-0.75(m,12H).13C NMR(126MHz,1,1,2,2-tetrachloroethane-d2)δ166.26,165.52,153.65,144.33(d,JF-C 1=244.5Hz),134.96,129.76(d,JF-C 3=10.0Hz),125.91,125.62(d,JF-C 4=3.7Hz),125.08,123.41,115.82,110.85(d,JF-C 2=19.8Hz),42.57,37.43,33.91,31.85,30.96,30.06,29.63,29.23,26.80,26.49,22.57,13.94.
质谱:HR-MALDI-TOF calcd.for C104H171Br2F2N4O2S2[M+H]+:1768.1172;found:1768.1185.
1d)聚合物PIBTzI-BT
将噻唑桥联异靛蓝-二溴(81mg,0.046mmol,1.0equiv.)、(2,2'-联噻吩-5,5'-二基)双三甲基锡(23mg,0.046mmol,1.0equiv.)、催化剂三(二亚苄基丙酮)二钯(1.3mg,0.00138mmol,0.03equiv.)和配体三(邻甲苯基)膦(3.4mg,0.011mmol,0.24equiv.)加入到干燥的反应瓶中,用氮气置换三次。随后在氮气保护下加入4mL无水甲苯,进行三次冷冻-抽气-解冻循环除氧,然后将反应混合物加热到110℃回流反应72小时。冷却后,加入10mL12mol/L的浓盐酸,200mL甲醇,室温下搅拌3小时,过滤。得到的沉淀物用索氏提取仪进行抽提纯化。分别用甲醇、丙酮、正己烷抽提至无色,再用三氯甲烷抽提,蒸除溶剂后用甲醇沉降,真空干燥后得到最终产物47mg,产率57.3%。
结构表征数据如下:
分子量:GPC:Mn=105.1kDa,Mw=196.5kDa,PDI=1.87,n=59。
元素分析:Anal.calcd.for C112H176F2N4O2S4:C 75.71,H 9.98,N 3.15;Found C75.28,H 9.88,N 3.37。
由上可知,该化合物结构正确,为式I所示化合物PIBTzI-BT,结构式如下所示:
其中,R为4-十八烷基二十二烷。
实施例2、聚合物PIBTzI-DFBT
2d)聚合物PIBTzI-DFBT
将噻唑桥联异靛蓝-二溴(100mg,0.046mmol,1.0equiv.)、(3,3'-二氟-[2,2'-联噻吩]-5,5'-二基)双三甲基锡(24mg,0.046mmol,1.0equiv.)、催化剂三(二亚苄基丙酮)二钯(1.3mg,0.00138mmol,0.03equiv.)和配体三(邻甲苯基)膦(3.4mg,0.01104mmol,0.24equiv.))加入到干燥的反应瓶中,用氮气置换三次。随后在氮气保护下加入4mL无水甲苯,进行三次冷冻-抽气-解冻循环除氧,然后将反应混合物加热到110℃回流反应72小时。冷却后,加入10mL12mol/L的浓盐酸,200mL甲醇,室温下搅拌3小时,过滤。得到的沉淀物用索氏提取仪进行抽提,分别用甲醇、丙酮、正己烷抽提至无色,再用三氯甲烷抽提,蒸除溶剂后用甲醇沉降,真空干燥后得到最终产物80mg,产率70.8%。结构表征数据如下:
分子量:GPC:Mn=45.9kDa,Mw=76.6kDa,PDI=1.67,n=25。
元素分析:Anal.calcd.for C112H174F4N4O2S4:C 74.20,H 9.67,N 3.09;Found C73.74,H 9.71,N 3.35。
由上可知,该化合物结构正确,为式I所示聚合物PIBTzI-DFBT,结构式如下所示:
其中,R为4-十八烷基二十二烷。
实施例3、聚合物PIBTzI-BT和PIBTzI-DFBT的光谱性能、电化学性能和场效应晶体管性能
1)聚合物PIBTzI-BT和PIBTzI-DFBT的光谱和电化学性能
图2为聚合物PIBTzI-BT和PIBTzI-DFBT在溶液和薄膜中的紫外可见吸收光谱。
由图2可知,聚合物PIBTzI-BT和PIBTzI-DFBT的光学带隙分别为1.75eV和1.76eV(光学带隙根据公式Eg=1240/λ计算,其中Eg为光学带隙,λ为紫外吸收曲线的边界值)。由图2可知,两个聚合物都具有比较强的分子内电荷转移峰,表明该聚合物分子间作用力较强。
图3为聚合物PIBTzI-BT和PIBTzI-DFBT薄膜的循环伏安曲线。测定在CHI660c电化学工作站进行,用传统的三电极结构测试,铂为工作电极,铂丝为对电极,银/氯化银为参比电极,四丁基六氟磷酸铵作为支持电解质。测试在乙腈溶液中进行。循环伏安的条件为:扫描范围为-1.8~1.8电子伏特(vs.Ag/AgCl),扫描速率为50毫伏每秒。两个聚合物都具有氧化峰和还原峰,可作为有机半导体材料。根据循环伏安曲线,聚合物PIBTzI-BT和PIBTzI-DFBT的HOMO能级分别为–5.47eV和–5.74eV,LUMO能级分别为–3.64eV和–3.59eV。聚合物具有合适的HOMO能级和LUMO能级,因而是双极性半导体材料。
2)聚合物PIBTzI-BT和PIBTzI-DFBT的场效应晶体管性能
图4为有机场效应晶体管的结构示意图,如图所示,采用玻璃作为衬底,在二次水、乙醇、丙酮中超声清洗后与80℃真空干燥。源漏电极为掩膜版热蒸镀的25nm厚的金为源、漏电极。实施例1~实施例2所得的聚合物为半导体活性层,将其浓度为10mg/ml的邻二氯苯溶液通过匀胶的方法在玻璃基底上形成有机半导体活性层,并在200℃热台上退火10分钟。
随后在实施例1~实施例2所得的聚合物薄膜表面通过匀胶形成900纳米厚的聚甲基丙烯酸甲酯作为场效应管介电层,90℃除溶剂60分钟;在绝缘层上通过掩膜版热蒸镀80nm厚铝作为栅电极,完成场效应管制备。
在室温下用通Keithley 4200SCS半导体测试仪测量了所制备的场效应器件的电学性能。决定OFET的性能的两个关键参数是:载流子的迁移率(μ)和器件的开关比(Ion/Ioff)。迁移率是指在单位电场作用下,载流子的平均漂移速度(单位是cm2 V-1s-1),它反映了在电场下空穴或电子在半导体中的迁移能力。开关比定义为:晶体管在“开”状态和“关”状态下的电流之比,它反映了器件开关性能的优劣。对于一个高性能的场效应晶体管,其迁移率和开关比应尽可能的高。
图5为基于两个噻唑桥联异靛蓝类聚合物所制备的场效应晶体管的转移特性曲线和输出特性曲线。两个聚合物场效应晶体管显示出了明显的双极性传输特性,说明噻唑桥联异靛蓝类聚合物是一类双极性半导体材料。
载流子迁移率可由方程计算得出:
IDS=(W/2L)Ciμ(VG–VT)2(饱和区)
其中,IDS为漏极电流,μ为载流子迁移率,VG为栅极电压,VT为阈值电压,W为沟道宽度,L为沟道长度,Ci为绝缘体电容。利用(IDS,sat)1/2对VG作图,并作线性回归,可由此回归线的斜率推算出载流子迁移率(μ),由回归线与X轴的截点求得VT。
迁移率可以根据公式从转移曲线的斜率计算得出,上述各例中制备的聚合物场效应晶体管的器件性能如表1所示。开关比可由图5源漏电流的最大值与最小值之比得出。
实验结果表明噻唑桥联异靛蓝类聚合物是一类优异的新型的双极性半导体材料。本发明并不限于所报道的两个材料,改变不同的侧链取代基和不同的给体单元可以得到一系列的聚合物,且本发明给出的合成方法简单、有效,对于合成新型双极性半导体材料有很大的指导意义。
表1、聚合物场效应晶体管的器件性能
Claims (10)
2.根据权利要求1所述的聚合物,其特征在于:R为碳原子总数为20-50的直链或支链烷基;n为25-59的整数。
6.根据权利要求4或5所述的方法,其特征在于:所述式IV所示化合物、双锡化合物、催化剂、配体的投料摩尔比依次为1.00:1.00:(0.03~0.1):(0.24~0.4);
所述聚合反应中,反应温度为110~115℃;反应时间为1小时~120小时。
9.权利要求1-3中任一项所述的聚合物作为双极性聚合物半导体材料在制备有机场效应晶体管器件中的应用。
10.一种有机场效应晶体管器件,所述有机场效应晶体管器件以权利要求1-3中任一项所述的聚合物为有机半导体活性层材料。
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