CN110183419A - 1,3,6,8位四取代芘衍生物的合成及其在有机场效应晶体管中的应用 - Google Patents
1,3,6,8位四取代芘衍生物的合成及其在有机场效应晶体管中的应用 Download PDFInfo
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
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- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/08—Hydrogen atoms or radicals containing only hydrogen and carbon atoms
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
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Abstract
本专利旨在开发具有半导体性能的一类1，3，6，8位四取代芘衍生物，并应用于有机场效应晶体管。芘的1，3，6，8位引入系列噻吩单元，构筑四取代芘衍生物，利用化学反应进行材料的制备；然后以硅片为栅极、以芘衍生物为有机半导体材料，制备底栅顶接触场效应晶体管。R为以下基团：
Description
技术领域
本发明涉及1，3，6，8位四取代芘衍生物功能材料的结构设计、化学合成及在有机场效应管中的应用研究。
背景技术
近年来，有机场效应晶体管(Organic Field-Effect Transistors，OFETs)在电子纸、智能卡、全有机主动显示、传感器、存储器等方面已有广泛应用。有机半导体是影响有机场效应晶体管性能的关键因素之一。芘分子平面性好，固态下具有良好的π-π堆积能力，其最高占据分子轨道(HOMO)与金电极功函数匹配度高，是有机半导体的良好构建母体(Yanbin Gong，Xuefeng Zhan，Qianqian Li，Zhen Li，Science China Chemistry，2016，59(12)：1623-1631.徐慧，刘霞，唐超，范曲立，黄维，南京邮电大学学报，2014，34(3)：111-124.)。
构建芘衍生物常用的方法是将芘溴化，然后通过偶联反应引入其它取代单元。噻吩是构建有机半导体最常见的结构单元之一，它具有良好的共轭体系与强给电子能力，固态下噻吩环硫原子之间的S-S作用力有助于提高材料的迁移率。界面修饰是提高半导体迁移率的常用途径。常用硅烷试剂(如：三氯十八烷基硅烷(OTS))自组装层或者高分子薄膜进行修饰。界面修饰可以提高半导体的成膜性，促进有机分子在硅片上的生长，从而提高半导体性能。
发明内容
1.本发明的特征是提供一类噻吩类基团在1，3，6，8位取代的芘衍生物，其结构通式如下所示：
R为以下结构：
2.本发明的另一特征是此类化合物在有机场效应晶体管中的应用。
附图说明
结合如下附图及详细描述将会更清楚地理解本发明的上述和其他特征及优点，其中：
图1 1，3，6，8-四(5′-正辛基-2′-噻吩基)芘的核磁氢谱；
图2 1，3，6，8-四(5′-正辛基-2′噻吩基)芘的核磁碳谱；
图3 1，3，6，8-四(5′-正辛基-2′-噻吩基)芘的OFET器件转移曲线图；
具体实施方案
实施案例1：
半导体材料的合成：
本发明中提供四种烷基化噻吩取代芘化合物的合成路线与步骤，以1，3，6，8-四(5′-正辛基-2′-噻吩基)芘为例。
合成路线：
2-辛基噻吩的合成：将噻吩(4.0g)溶于无水甲苯(50mL)中，降温至0℃，加入无水SnCl4(6.0mL)，搅拌10分钟后，滴加辛酰氯(7.88mL)；完成后，升至室温；搅拌6小时，加入水淬灭反应，用乙酸乙酯萃取，合并有机相，无水MgSO4干燥，抽滤，旋蒸，得到的酰基化产物不经纯化直接用于下一步。将所得的油状中间体加入100mL单口烧瓶，加入氢氧化钾(18.80g)、水合肼(15mL)、正辛醇(10mL)，加热至回流；反应8小时，冷却至室温，加入水，用乙酸乙酯萃取产物，无水MgSO4干燥，过滤，旋蒸。粗产品用硅胶柱分离得到无色油状物纯品，洗脱剂为石油醚。1H NMR(CDCl3，300MHz，298K)δ：7.10(d，1H，J＝3Hz)，6.92(t，1H，J＝3Hz)，6.78(d，1H，J＝3Hz)，2.82(t，2H，J＝6Hz)，1.73-1.63(m，2H)，1.33-1.28(m，10H)，0.89(t，3H，J＝6Hz).
5-正辛基-2-三丁基锡基噻吩的合成：将2-正辛基噻吩(1.96g)溶于无水THF(50mL)中，降温至-78℃，滴加n-BuLi(2.5M，4.4mL)；完成后，在此温度下继续搅拌1小时；注射器加入三丁基氯化锡3.20(mL)，升至室温搅拌过夜，加入水淬灭反应，乙醚萃取产物。合并有机相，依次用饱和食盐水、水洗涤，无水MgSO4干燥，过滤，旋蒸，得到淡黄色油状物，不经纯化直接用于下一步反应。
1，3，6，8-四溴芘的合成：单口烧瓶中，加入芘(2.50g)，硝基苯(80mL)，加热至(80℃)，加入液溴(8.75g)，加热至120℃继续反应12小时，冷却至室温，加入乙醇，抽滤，用丙酮洗涤，得到黄色固体。此固体在常见有机溶剂中均不溶，不经纯化，直接用于下一步反应。
1，3，6，8-四(5′-辛基-2′-噻吩基)芘的合成：在50mL Schlenk瓶中，加入1，3，6，8-四溴芘(0.26g)、2-辛基-5-三丁基锡基噻吩(1.50g)、无水THF(25mL)、Pd(PPh3)2Cl2(116mg)，氮气下升温至80℃反应过夜。降温至室温，加入水，用二氯甲烷萃取，合并有机相，无水MgSO4干燥，旋蒸，硅胶柱分离(石油醚)，然后用二氯甲烷/甲醇重结晶得到黄色固体。1HNMR(300MHz，CDCl3，298K)δ：8.55(s，4H)，8.19(s，2H)，7.19(d，4H，J＝3Hz)，6.90(d，4H，J＝3Hz)，2.92(t，8H，J＝6Hz)，1.83-1.73(m，8H)，1.48-1.31(m，40H)，0.90(t，12H，J＝6Hz).13CNMR(300MHz，CDCl3，298K)δ：148.9，142.0，133.4，132.7，131.3，130.5，128.7，128.2，127.1，34.5，34.4，32.9，32.0，31.8，25.3，16.7.MALDI-TOF-MS理论值：979.93；测得值：979.53。元素分析理论值：C 78.47，H 8.44；测得值：C 78.65，H 8.38。
实施案例2：
有机薄膜场效应晶体管的制备与表征：
(1)栅极采用n型掺杂硅片(表面为300nm厚的SiO2绝缘层)，将其裁成1.5cm×1.5cm的尺寸，切割好后的硅片用丙酮、乙醇、去离子水分别超声15分钟，再用氮气吹干，放入烘箱中干燥，再用UV-臭氧照射10分钟。
(2)在表面皿中加入10mL甲苯，再加入13uL三氯十八烷基硅烷，搅拌均匀后，加入硅片，浸泡2小时。浸泡完成后，基片用甲苯、丙酮、乙醇分别超声15分钟，氮气枪吹干，放入烘箱中干燥。
(3)将装有50-60mg有机材料的坩埚连到电极上，将OTS修饰的基片、未修饰的基片固定在托架上；先用机械泵再用分子泵将系统抽真空至4-5×10-4Pa。加热蒸镀半导体层薄膜，通过控制加热温度控制蒸镀速度为用石英晶振片监测半导体层厚度约为50nm。半导体层蒸镀完成后，关闭挡板，关闭加热器，冷却一小时；加上源漏电极的掩膜板，蒸镀金电极，金的蒸发速率在金电极厚度控制在50nm左右。晶体管的沟道宽度、长度分别为1500um×100um。蒸镀完金电极，系统冷却一小时后，取出器件。
(4)器件性能测试：使用Keithley 4200半导体测试仪在空气中对器件进行性能测试。迁移率、开关比和阈值电压是场效应晶体管性能的关键参数。迁移率、阈值电压可从电流-电压曲线饱和区中测出。采取负向偏压，源漏电压为-80V，扫描范围为10--80V。在空白硅片上未能检测到场效应，在OTS修饰的晶体管迁移率平均值为2.5×10-4cm2V-1s-1，最大迁移率为4×10-4cm2V-1s-1。
表1：1，3，6，8-四(5′-辛基-2′-噻吩基)芘材料在不同修饰基片上构筑OTFT的性能
Claims (4)
1.用于有机场效应晶体管中有机半导体材料1，3，6，8位四取代芘衍生物，其结构为：
R为以下基团：
2.根据权利要求1所述有机半导体材料1，3，6，8位噻吩四取代芘衍生物，其特征在于：R为结构式为
3.根据权利要求2所述1，3，6，8位噻吩四取代芘的合成方法，其合成路线为：
4.根据权利要求2所述1，3，6，8位噻吩四取代芘衍生物在有机场效应晶体管中的应用。
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