CN109096342B - 一种吡咯并吡咯二酮类环状共轭化合物及其制备方法与应用 - Google Patents
一种吡咯并吡咯二酮类环状共轭化合物及其制备方法与应用 Download PDFInfo
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Abstract
Description
技术领域
本发明涉及一种吡咯并吡咯二酮类环状共轭化合物及其制备方法与应用。
背景技术
吡咯并吡咯二酮(Diketopyrrolopyrrole)类化合物是一种重要的有机光电材料。该类材料合成简便成本低廉,具有良好的光热稳定性、宽而强的吸收光谱、优异的结晶性,因而被广泛应用于有机半导体器件中,比如有机场效应晶体管(Adv.Mater.,2016,28,943-950.)、有机太阳能电池(Acc.Chem.Res.,2016 49,78-85.)。然而到目前为止所有的吡咯并吡咯二酮化合物均为结晶性特别强的线型、星型等平面小分子和聚合物,这些分子在薄膜中通常易聚集形成大尺度结晶区块,导致薄膜形貌不理想;同时材料在环境友好的低沸点非卤素溶剂中溶解性有限,这些因素都不利于该材料的大规模工业化应用。因此,通过简单高效的合成方法得到低聚集倾向的三维结构吡咯并吡咯二酮类化合物具有重要的研究意义和实用价值。
环状共轭分子由于其特殊的三维立体构型在超分子化学、载流子输运等方面有独特优势。目前报道的环装共轭分子大都集中在联苯、并苯类环状分子(J.Am.Chem.Soc.2017,139,18480-18483.;Science 2017,356,172-175.),合成此类环状共轭分子的方法也未曾适用于吡咯并吡咯二酮分子,也没有吡咯并吡咯二酮类环状共轭分子报道。
发明内容
本发明的目的是提供一种吡咯并吡咯二酮类环状共轭化合物及其制备方法与应用。
本发明提供的一种吡咯并吡咯二酮类环状共轭化合物,其结构式如下式Ⅰ所示:
式Ⅰ中,R1、R2独立地是氢、C1~C50的直链或叉链烷基、C1~C50的含酰胺键、醚键、酯键的直链或叉链烷基、C1~C50的直链或叉链全氟代烷基中的一种;
R3、R4独立地是取代或未取代的苯基、噻吩基、噻唑基、吡啶基、喹啉基、呋喃基、吡咯基、咪唑基、萘基和芘基中的一种或者几种通过单键、双键、三键、氧、硫或氮相连的组合片段;
n为2~20之间的整数。
上述的化合物中,n为2~10之间的整数,具体可为4、2~4、4~10或2~6。
上述的化合物中,R1、R2独立地是氢、C1~C20的直链或叉链烷基、C1~C20的含酰胺键、醚键、酯键的直链或叉链烷基、C1~C20的直链或叉链全氟代烷基中的一种;具体可为C8的直链或叉链烷基。
本发明还提供了上述的吡咯并吡咯二酮类环状共轭化合物的制备方法,包括如下步骤:
1)在有机溶剂Ⅰ中,将双锡取代的吡咯并吡咯二酮、(1,5-环辛二烯)二氯化铂(II)混合,并进行加热反应,得到中间产物1;反应式如下所示:
2)在有机溶剂Ⅱ中,将步骤1)得到的中间产物1与1,1'-双(二苯基膦)二茂铁混合反应,得到中间产物2;反应式如下所示:
3)在有机溶剂Ⅲ中,将步骤2)得到的中间产物2与三苯基膦混合,并进行加热反应,即得到所述吡咯并吡咯二酮类环状共轭化合物。
上述的方法中,步骤3)的反应式如下所示:
上述的方法中,所述有机溶剂Ⅰ、所述有机溶剂Ⅱ、所述有机溶剂Ⅲ均选自四氢呋喃(THF)、甲苯(toluene)、二氯甲烷、氯仿、N-甲基吡咯烷酮(NMP)、二甲基甲酰胺(DMF)、二甲基乙酰胺(DMAC)、二甲亚砜(DMSO)、六甲基磷酰胺(HMP)、环丁砜、乙腈和苯甲腈中的一种。
上述的方法中,步骤1)中,所述双锡取代的吡咯并吡咯二酮与所述(1,5-环辛二烯)二氯化铂(II)的摩尔比可为1:0.05~20,具体可为1:1、1:0.05~1、1:1~20或1:0.05~10;
步骤2)中,所述中间产物1与所述1,1'-双(二苯基膦)二茂铁的摩尔比可为1:1~20,具体可为1:1、1:0.05~1、1:1~20或1:0.05~10;
步骤3)中,所述中间产物2与所述三苯基膦的摩尔比可为1:1~20,具体可为1:10、1:1~10、1:10~20或1:5~15;
上述的方法中,步骤1)中,所述有机溶剂Ⅰ的体积与所述双锡取代的吡咯并吡咯二酮的质量比为10~400ml:1g;
步骤2)中,所述有机溶剂Ⅱ的体积与所述1,1'-双(二苯基膦)二茂铁的质量比为10~400ml:1g;
步骤3)中,所述有机溶剂Ⅲ的体积与所述三苯基膦的质量比为10~400ml:1g。
上述的方法中,步骤1)中,所述加热反应的条件如下:在惰性气体保护下,加热至30~150℃,具体可为70℃、30~70℃、70~150℃或50~100℃,反应1~24小时,具体可为12小时、1~12小时、12~24小时或5~20小时;
步骤2)中,所述反应的条件如下:在惰性气体保护下,反应的温度为室温,反应1~24小时,具体可为12小时、1~12小时、12~24小时或5~20小时;
步骤3)中,所述加热反应的条件如下:在惰性气体保护下,加热至70~110℃,在70~110℃时反应1~24小时,具体可为12小时、1~12小时、12~24小时或5~20小时;
所述惰性气体具体为氮气或氩气。
本发明中,所述室温为本领域中公知的常识,指的是10~30℃。
上述的方法中,步骤1)-3)中,均包括在反应结束后对反应体系进行后处理的步骤;
所述后处理过程如下:将所述反应体系冷却后除去溶剂,加入甲醇、乙醇、异丙醇、正己烷或正戊烷过滤得到滤饼;然后将所述滤饼干燥。
上述的方法中,所述干燥的条件为真空干燥箱25~150℃干燥1~24小时,具体可为50℃干燥5小时;
步骤3)中,经过所述后处理之后对所述滤饼进行硅胶柱色谱分离,得到所述吡咯并吡咯二酮类环状共轭化合物。
本发明所述的吡咯并吡咯二酮类环状共轭化合物在制备有机半导体器件中的应用。
上述的应用中,所述有机半导体器件包括场效应晶体管、有机太阳能电池和有机发光二极管中的至少一种。
本发明具有以下优点:
1、合成步骤简短,条件温和,操作简便。
2、合成中所用原料方便易得,易于工业化生产。
3、该类化合物拥有很好的化学稳定性。
4、该类化物对可见光有较强的吸收。
5、该类化合物独特的环装构型有利于抑制分子聚集,形成三维电荷传输通道。
附图说明
图1为本发明实施例1的吡咯并吡咯二酮类环状共轭分子C-DPP1的1H-NMR图。
图2为本发明实施例1的吡咯并吡咯二酮类环状共轭分子C-DPP1的13C-NMR图。
图3为本发明实施例1的吡咯并吡咯二酮类环状共轭分子C-DPP1的质谱图。
图4为本发明实施例2的吡咯并吡咯二酮类环状共轭分子C-DPP2的1H-NMR图。
图5为本发明实施例2的吡咯并吡咯二酮类环状共轭分子C-DPP2的13C-NMR图。
图6为本发明实施例2的吡咯并吡咯二酮类环状共轭分子C-DPP2的质谱图。
图7为本发明实施例1的吡咯并吡咯二酮类环状共轭分子C-DPP1的场效应晶体管器件结构图。
图8为本发明实施例1的吡咯并吡咯二酮类环状共轭分子C-DPP1的有机太阳能电池器件结构图。
图9为本发明实施例1的吡咯并吡咯二酮类环状共轭分子C-DPP1的有机发光二极管器件结构图。
图10为本发明实施例1的吡咯并吡咯二酮类环状共轭分子C-DPP1的有机发光二极管器件发光图谱(a)和发光量子效率图谱(b)。
具体实施方式
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。
实施例1
本实施例吡咯并吡咯二酮类环状共轭分子(记为C-DPP1)的合成路线如下:
具体合成步骤是:
(1)向装有850.4mg双锡取代的吡咯并吡咯二酮1的反应瓶中加入374.2mg(1,5-环辛二烯)二氯化铂(II)。在氮气保护下,注入400ml无水四氢呋喃(THF),70摄氏度搅拌;反应12小时后,产物冷却后旋干,加入约50ml甲醇,过滤,滤饼放置于真空干燥箱50摄氏度干燥5小时,得到产物2a。
(2)向装有上述步骤所得产物2a的反应瓶中加入1,1'-双(二苯基膦)二茂铁(dppf)554.4mg。在氮气保护下,注入400ml无水二氯甲烷,室温搅拌反应12小时后,产物冷却后旋干,加入约50ml甲醇,过滤,滤饼放置于真空干燥箱50摄氏度干燥5小时,得到产物2b。
(3)向装有上述步骤所得产物2b的反应瓶中加入三苯基膦(PPh3)2.62g,在氮气保护下,注入400ml无水甲苯,110摄氏度搅拌反应12小时后,产物冷却后旋干,加入约50ml甲醇,过滤,滤饼放置于真空干燥箱50摄氏度干燥5小时,得到粗产物C-DPP1。粗产物经过硅胶柱分离、重结晶、高效液相色谱分离后得到纯净的C-DPP183.6mg,三步反应总产率16%。
上述制备得到C-DPP1的结构确证如下:
1H NMR(400MHz,298K,CDCl3,ppm)δ=8.18-8.17(d,8H),7.36-7.35(d,8H),3.91-3.90(m,16H),1.75(m,8H),1.35-1.26(m,64H),0.89-0.85(m,48H).13C NMR(100MHz,298K,CDCl3,ppm)δ=162.0,141.3,140.6,134.7,130.2,125.5,112.4,45.6,39.2,30.4,28.6,28.5,23.8,23.1,14.2,10.6,10.5.MS.HRMS(MALDI-TOF):m/z calcd for C120H153N8O8S8[M+H]+:2089.95716,found.2089.95849.
C-DPP1的1H-NMR图如图1所示,碳谱图如图2所示,质谱图如图3所示。
实施例2、
本实施例吡咯并吡咯二酮类环状共轭分子(记为C-DPP2)的合成路线如下:
具体合成步骤与本发明实施例1一致,唯一不同的是使用正辛基取代的3作为起始原料,C-DPP2的结构确证结果:1H-NMR图如图4所示,13C-NMR图如图5所示,质谱图如图6所示。
实施例3、
吡咯并吡咯二酮类环状共轭分子场效应晶体管器件:
场效应晶体管器件结构为底栅-顶接触,具体结构如图7所示:源漏电极均为厚度为25nm的蒸镀而得的金层,栅电极为厚度为400μm的硅,绝缘层为OTS(octadecyltrichlorosilane)修饰的厚度为300nm的二氧化硅,有机半导体部分为厚度为40-60nm的C-DPP1。
将本发明实施例1所得吡咯并吡咯二酮类环状共轭分子C-DPP1作为活性层溶于氯仿和体正己烷的混合溶液(体积比为10:1),浓度为10mg/mL,采用旋涂法涂覆在OTS(octadecyltrichlorosilane)修饰的厚度为300nm的二氧化硅/硅(SiO2/Si)基底上,作为有机场效应晶体管器件的有机半导体部分,该层的厚度为40-60nm。测试结果显示,该材料在150摄氏度退火10分钟后空穴迁移率为3.4×10-3cm2V-1s-1,电子迁移率为2.3×10-4cm2V- 1s-1,证明该材料在有机场效应晶体管方面有潜在应用价值。
实施例4、
本发明实施例1中制备得到的吡咯并吡咯二酮类环状共轭分子C-DPP-1在制备有机太阳能电池器件中的应用:
有机太阳能电池的具体器件结构如附图8所示:在玻璃基底上以氧化铟锡/氧化锌(ITO/ZnO)为电极,在其上旋图有机半导体活性层,上面再以三氧化钼/银(MoO3/Ag)为电极。其中氧化锌层厚度约40nm,活性层厚度约80nm,氧化钼约10nm,银约100nm。
本发明实施例1所得吡咯并吡咯二酮类环状共轭分子C-DPP-1作为电子受、聚3-己基噻吩(P3HT)作为电子给体应用到非富勒烯太阳能电池中,以氧化铟锡/氧化锌(ITO/ZnO)和三氧化钼/银(MoO3/Ag)为电极。活性层C-DPP-1:P3HT采用10mg/ml的氯仿溶液旋涂的方法得到,器件的最优条件下,得到能量转换效率0.49%,其中短路电流密度(Jsc)为1.65mA·cm-2,开路电压(Voc)为0.67V和填充因子(FF)为0.44,证明该材料在有机太阳能电池方面有潜在应用价值。
实施例5、
本发明实施例1中制备得到的吡咯并吡咯二酮类环状共轭分子C-DPP-1制备有机发光二极管器件:
有机发光二极管器件的具体器件结构如附图9所示:在玻璃基底上以氧化铟锡/PEDOT:PSS为电极,在其上旋图有机半导体活性层,上面再以氟化锂/铝(LiF/Al)为电极。其中PEDOT:PSS层厚度约40nm,活性层厚度约80nm,氟化锂约1nm,铝约100nm。
本发明实施例1所得吡咯并吡咯二酮类环状共轭分子C-DPP-1作为活性层,以氧化铟锡/PEDOT:PSS和氟化锂/铝(LiF/Al)为电极。活性层C-DPP-1采用在10mg/ml的氯仿溶液旋涂的方法得到,器件在不同电流下的发光图谱和不同偏压下的发光量子效率附图10所示,证明该材料在近红外发光方面有潜在应用价值。
Claims (10)
3.根据权利要求2所述的方法,其特征在于:所述有机溶剂Ⅰ、所述有机溶剂Ⅱ、所述有机溶剂Ⅲ均选自四氢呋喃(THF)、甲苯(toluene)、二氯甲烷、氯仿、N-甲基吡咯烷酮(NMP)、二甲基甲酰胺(DMF)、二甲基乙酰胺(DMAC)、二甲亚砜(DMSO)、六甲基磷酰胺(HMP)、环丁砜、乙腈和苯甲腈中的一种;
步骤1)中,所述双锡取代的吡咯并吡咯二酮与所述(1,5-环辛二烯)二氯化铂(II)的摩尔比为1:0.05~20;步骤2)中,所述中间产物1与所述1,1'-双(二苯基膦)二茂铁的摩尔比为1:1~20;步骤3)中,所述中间产物2与所述三苯基膦的摩尔比为1:1~20。
4.根据权利要求2或3所述的方法,其特征在于:步骤1)中,所述有机溶剂Ⅰ的体积与所述双锡取代的吡咯并吡咯二酮的质量比为10~400ml:1g;步骤2)中,所述有机溶剂Ⅱ的体积与所述1,1'-双(二苯基膦)二茂铁的质量比为10~400ml:1g;步骤3)中,所述有机溶剂Ⅲ的体积与所述三苯基膦的质量比为10~400ml:1g。
5.根据权利要求2或3所述的方法,其特征在于:步骤1)中,所述加热反应的条件如下:在惰性气体保护下,加热至30~150℃,反应1~24小时;步骤2)中,所述反应的条件如下:在惰性气体保护下,反应的温度为室温,反应1~24小时;步骤3)中,所述加热反应的条件如下:在惰性气体保护下,加热至70~110℃,在70~110℃时反应1~24小时。
6.根据权利要求5所述的方法,其特征在于:所述惰性气体为氮气或氩气。
7.根据权利要求2或3所述的方法,其特征在于:步骤1)-3)中,均包括在反应结束后对反应体系进行后处理的步骤;所述后处理过程如下:将所述反应体系冷却后除去溶剂,加入甲醇、乙醇、异丙醇、正己烷或正戊烷过滤得到滤饼;然后将所述滤饼干燥。
8.根据权利要求7所述的方法,其特征在于:所述干燥的条件为真空干燥箱25~150℃干燥1~24小时;步骤3)中,经过所述后处理之后对所述滤饼进行硅胶柱色谱分离,得到所述吡咯并吡咯二酮类环状共轭化合物。
9.权利要求1所述的吡咯并吡咯二酮类环状共轭化合物在制备有机半导体器件中的应用。
10.根据权利要求9所述的应用,其特征在于:所述有机半导体器件包括场效应晶体管、有机太阳能电池和有机发光二极管中的至少一种。
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