CN112409387A - 以还原橙1为中心核的a-d-a型有机小分子光伏材料 - Google Patents
以还原橙1为中心核的a-d-a型有机小分子光伏材料 Download PDFInfo
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Abstract
本发明属于有机光电材料技术领域，具体涉及一种以还原橙1为中心核的A‑D‑A型结构有机小分子光伏材料，以染料还原橙1衍生物为给体单元(D)，吡咯并吡咯二酮衍生物为受体单元(A)，并以烷基链进行修饰，通过烷基化反应和Suzuki偶联反应，获得一种以烷基侧链修饰的还原橙1为中心核的A‑D‑A型结构有机小分子光伏材料，其以富勒烯PC71BM为受体的单层器件本体异质结太阳能电池的最大能量转化效率和短路电流分别高达1.0％和4.31mA cm‑2。本发明所涉及的发明材料具有良好的溶解性和稳定性，以及一定的光电转化能力，有望用于有机太阳能电池的给体材料。
Description
技术领域
本发明涉及有机小分子光伏领域，特别涉及了一种以烷基侧链修饰的还原橙1为中心核的A-D-A型结构有机小分子光伏材料的合成及应用。
技术背景
近年来受到越来越多的关注的有机太阳能电池(OSCs)由于具有成本低、重量轻、机械柔性好等优点，是下一代清洁和可再生能源的重要发展方向，有着广阔的应用前景。随着这一领域的快速发展，基于富勒烯PCBM为受体的聚合物太阳能电池(PSCs)单层器件的光电转换效率(PCE)已达到11.7％[1]，其基于非富勒烯受体的单层器件的效率超过了16％[2]。然而，由于聚合物存在重现性差、纯化复杂、活性材料的结构与性能关系不明确等缺点。与聚合物相比，小分子给体材料具有易于纯化、结构确定等特点，可以保证器件性能的重现性等优点[3,4]，目前基于溶液加工的小分子太阳能电池(SMSCs)的单层器件光电转换效率(PCE)达到了11.5％[5]。
科学研究者合成了大量具有A-D-A骨架的小分子太阳能电池材料，并***研究了它们的光电性能。如含有不同端基和末端基团的引达省二噻吩(IDT)[6]、二噻吩硅芴(DTS)[7]、苯并二噻吩(BDT)[8]和卟啉[9]等不同核的小分子太阳能电池(SMSCs)。这种设计策略可有效地解决小分子给体材料成膜质量差的科学问题，同时，有机小分子由于其主链结构的高效共轭以及端基受体单元与中心给体核之间的分子内存在电荷转移(ICT)，而表现出较高的载流子迁移率和摩尔吸光系数。
多环芳香族化合物在光电领域的应用越来越受到人们的青睐。主要是因为多环大π稠环核具有更大的π电子离域范围，刚性结构的大π稠环核的重组能较低，有利于获得较高的载流子迁移率[9-10]。之前就有相关同分异构体大稠环光电材料的报道[11-14]。基于上述考虑，为了获得平面性好且具有较高载流子迁移率的给体材料，于是我们以多环大π稠环核还原橙1为起始原料制作中心给体核，以吡咯并吡咯二酮为受体单元，嫁接噻吩桥联，设计并合成了一种A-D-A型线型小分子给体材料，***研究了它们的分子结构对材料热稳定性以及光伏性能的影响。
附：主要参考文献
[1]Zhao J,Li Y,Yang G,et al.Nature Energy,2016,1(2):15027.
[2]Fan B,Zhang D,Li M,et al.Science China Chemistry,2019:1-7.
[3]Welch G C,Perez L A,Hoven C V,et al.Journal of MaterialsChemistry,2011,21(34):12700-12709.
[4]D.Demeter,T.Rousseau,P.Leriche,T.Cauchy,R.Po and J.Roncali,Adv.Funct.Mater.21(2011)4379-4387.
[5]Wan J,Xu X,Zhang G,et al.Energy&Environmental Science,2017,10(8):1739-1745.
[6]Liu D,Xiao M,Du Z,et al.Journal of Materials Chemistry C,2014,2(36):7523-7530.
[7]Sun Y,Seifter J,Huo L,et al.Advanced Energy Materials,2015,5(3):1400987.
[8]Lin Y,Ma L,Li Y,et al.Advanced Energy Materials,2013,3(9):1166-1170.
[9]Qin H,Li L,Guo F,et al.Energy&Environmental Science,2014,7(4):1397-1401.
[10]Liu B,Duan L,Chen J,et al.Dyes and Pigments,2017,139:42-49.
[11]Giguère J B,Verolet Q,Morin J F.Chemistry–A European Journal,2013,19(1):372-381.
[12]Matsuno T,Kamata S,Hitosugi S,et al.Chemical Science,2013,4(8):3179-3183.
[13]Giguère J B,Morin J F.The Journal of organic chemistry,2013,78(24):12769-12778.
[14]Giguère J B,Boismenu-Lavoie J,Morin J F.The Journal of organicchemistry,2014,79(6):2404-2418.
发明内容
针对现有技术所存在的问题，我们发明了一种基于染料还原橙1衍生物为中心核的A-D-A型结构有机小分子光伏材料，该类材料的特点是以染料还原橙1衍生物为给体单元(D)，吡咯并吡咯二酮衍生物为受体单元(A)，并以烷基链进行修饰。利用这类A-D-A型结构有机小分子光伏材料，通过溶液加工，制作了有机小分子光伏器件(OSCs)。实现了以廉价的染料还原橙1为起始原料构筑成A-D-A型结构光伏材料的太阳能电池光电转换。
因此，本发明的目的在于提供一种价格低廉的，且具有一定光电转换能力的小分子光伏材料，该材料具有较好的成膜性；在与PC71BM共混的情况下，该类材料具有较好的光电转化效率。
本材料在经典D-A结构基础上，通过引入平面大稠环结构的DBP单元，旨在实现较大的电荷离域范围，提高载流子迁移率。其中DBP单元的设计与合成属于首创，发明的DBP单元以及小分子DBP-DPP2和DBP(T-DPP)2有利于有机光伏供体材料的分子构筑及其在溶剂加工型本体异质结有机太阳能电池中的应用。这类A-D-A型结构材料的分子结构以及中间体可以是下列分子的任何一种。
上述A-D-A型有机小分子光伏材料，包括下面任何衍生物：
以2,9-二溴-7,14-二(异辛氧基)二苯并芘(DBP)为推电子基团，以2-己基癸烷吡咯并吡咯二酮(DPP)为拉电子基团的A-D-A型小分子光伏材料DBP-DPP2。
以2,9-二溴-7,14-二(异辛氧基)二苯并芘(DBP)为推电子基团，噻吩单元为连接π桥，以2-乙基己烷吡咯并吡咯二酮衍生物为拉电子基团的A-D-A型小分子光伏材料DBP(T-DPP)2。
以下为具体合成路线：
为了得到上述材料，本发明的合成方案如下：
A-D-A型小分子光伏材料给体核DBP合成：还原橙1(Vat Orange1)在氢氧化钠溶液,Aliquat 336和保险粉的作用下,在加热的条件下，与溴代异辛烷发生亲核取代反应，合成得到具有异辛氧基侧链的DBP粗产品，经柱层析分离得到纯品。
A-D-A型小分子光伏材料目标分子DBP-DPP2的合成：侧链DPP-Bpi与给体核DBP在与碳酸钠溶液以及Aliquat 336相互作用条件下，用四三苯基膦钯催化发生Suzuki偶联反应，合成得到A-D-A型小分子光伏材料DBP-DPP2，粗产品经柱层析分离得到纯品。
A-D-A型小分子光伏材料目标分子DBP(T-DPP)2的合成：侧链DPP-T-Bpi与给体核给体核DBP在与碳酸钠溶液以及Aliquat 336相互作用条件下，用四三苯基膦钯催化发生Suzuki偶联反应，合成得到A-D-A型小分子光伏材料DBP(T-DPP)2，粗产品经柱层析分离得到纯品。
本发明的A-D-A型小分子光伏材料与已公开的大多数小分子光伏材料相比，其特点是：(1)由于中心核的起始原料为价格低廉的工业染料还原橙1，另一名称是还原黄RK，受体单元也是染料吡咯并吡咯二酮，因此设计的A-D-A型小分子材料制备成本更低，原料来源更加广泛；(2)并且分别引入2-乙基己烷和2-己基癸烷进行修饰，在易于调节溶解性的同时，使小分子材料具有更好的成膜性；(3)噻吩桥的引入很好的拓宽了分子的吸收范围以及使小分子材料具有更强的分子间相互作用，更紧密的π-π堆积作用；(4)分子中给受体相互作用的存在，形成强的ICT作用，增强电荷传输性能。因此，这类材料是一类很有发展前景的有机小分子光伏材料。
本发明的应用在于：将设计的光伏小分子材料作为给体，与PC71BM在不同比列下共混，制作光伏器件，实现将太阳能较好的转换为电能。
所述的有机小分子光伏器件包括氧化锡铟导电玻璃衬底层(ITO)，阳极层。其中阳极修饰层为聚二氧乙基噻吩(PEDOT，30nm)涂层；阴极为Ca(10nm)/Al(100nm)的沉积层；活化层材料为本发明所述的A-D-A分子与PC71BM，其共混重量比为1:2。
附图说明
图1为本发明DBP(T-DPP)2的热失重曲线图
图2为本发明DBP(T-DPP)2与PC71BM的混合比例为1:2(w/w,12mg/mL)下的J-V曲线图
图3为本发明DBP(T-DPP)2与PC71BM的混合比例为1:2(w/w,12mg/mL)下的EQE曲线图
图4为DBP(T-DPP)2与PC71BM的混合比例为1:2(w/w,12mg/mL)时单电子器件的J1/2-V曲线
图5为本发明中材料的分子结构创新点
具体实施方式
下面通过具体实施例对本发明作进一步说明，但这些具体实施方案不以任何方式限制本发明的保护范围。
实施例1
2,9-二溴-7,14-二(异辛氧基)二苯并芘(DBP)的合成
氮气保护下，于250毫升单口瓶中装有还原橙1(1.0g,2.16mmol),氢氧化钠溶液(0.1m,100mL,10mmol),Aliquat 336(1060mg,1.2mL,2.62mmol),保险粉(970mg,5.56mmol),和溴代异辛烷(3.0mL,3.32g,17.24mmol).反应液加热到80℃反应3h，直到反应体系变成无色。将水轻轻倒出，然后加入甲醇30mL。将粗产品抽滤出来，然后用甲醇洗涤。用硅胶柱层析纯化(二氯甲烷/石油醚1:2v/v)得到DBP产品为橙色固体(1088mg,73％).1HNMR(400MHz,CDCl3)δ8.71(d,J＝9.2Hz,2H),8.66(d,J＝9.6Hz,2H),8.63(s,2H),8.34(d,J＝9.4Hz,2H),7.78(d,J＝8.1Hz,2H),4.08(d,J＝5.4Hz,4H),2.13-1.98(m,2H),1.95-1.64(m,8H),1.58(s,4H),1.25(s,4H),1.17-1.01(m,12H).
实施例2
DBP-DPP2的合成
化合物DPP-Bpi(420mg,0.48mmol)和2,9-二溴-7,14-二(异辛氧基)二苯并芘(DBP)(165mg,0.24mmol，1eq)溶解于30mL甲苯中,2M Na2CO3溶液(5eq),Aliquote336(0.5mL)。反应体系反复排氧和抽取氮气三次，四三苯基膦钯(16.5mg,0.0143mmol)加到反应体系中,体系在80℃下反应24h。反应停止后，倒入水中用三氯甲烷萃取三遍.有机层用无水硫酸镁干燥后，减压旋蒸出溶剂.使用洗脱剂为(石油醚/二氯甲烷体＝1:1)的混合溶液柱层析纯化，获得绿色的固体产物AAN-DPP2(198mg,yield:60％).1H NMR(400MHz,CDCl3)δ8.84(d,J＝3.8Hz,2H),8.78(d,J＝13.8Hz,4H),8.51(s,2H),8.38(d,J＝9.2Hz,2H),7.81(d,J＝8.5Hz,2H),7.51(d,J＝5.5Hz,2H),7.37(s,2H),7.21-7.13(m,4H),7.12(d,J＝4.3Hz,2H),4.15(s,4H),3.96(dd,J＝14.2,7.8Hz,8H),2.17-2.09(m,2H),2.01(dt,J＝14.5,7.0Hz,4H),1.90-1.74(m,8H),1.29-1.18(m,104H),1.08(t,J＝6.9Hz,12H),0.86-0.78(m,24H).
实施例3
DBP(T-DPP)2的合成
化合物DPP-T-Bpi(176mg,0.24mmol)和2,9-二溴-7,14-二(异辛氧基)二苯并芘(DBP)(83mg,0.12mmol，1eq)溶解于30mL甲苯中,2M Na2CO3溶液(5eq),Aliquote336(0.5mL)。反应体系反复排氧和抽取氮气三次，四三苯基膦钯(8.3mg,0.0072mmol)加到反应体系中,体系在80℃下反应24h。反应停止后，倒入水中用三氯甲烷萃取三遍.有机层用无水硫酸镁干燥后，减压旋蒸出溶剂.使用洗脱剂为(石油醚/二氯甲烷体＝1:1)的混合溶液柱层析纯化，获得绿色的固体产物DBP(T-DPP)2(127mg,yield:60％).1H NMR(400MHz,CDCl3)δ8.84(d,J＝7.8Hz,2H),8.78(d,J＝8.0Hz,2H),8.70(d,J＝7.4Hz,2H),8.62(s,2H),8.48(d,J＝9.2Hz,2H),8.24-8.15(m,4H),8.10(d,J＝9.2Hz,2H),7.46(s,2H),7.37(s,2H),7.31(s,2H),7.09(s,2H),4.54-4.39(m,8H),4.30-4.25(m,4H),2.14(s,4H),1.92(s,2H),1.87-1.67(m,12H),1.38(d,J＝97.3Hz,36H),1.14(s,12H),0.95(ddd,J＝21.0,15.3,6.8Hz,24H).
实施例4
A-D-A型小分子光伏材料的性能表征及其光伏光器件的制作和发光性能的测试
A-D-A型小分子光伏材料的1H NMR光谱通过Bruker Dex-400NMR仪器测定，紫外-可见吸收光谱通过HP-8453紫外-可见光谱仪测定，荧光光谱通过HITACHI-850荧光光谱仪测定。
基于A-D-A型小分子材料的光伏器件包括：氧化锡铟(ITO)导电玻璃阳极层、聚二氧乙基噻吩(PEDOT)阳极修饰层。活化层层由所述小分子材料和PC71BM共混构成，其共混比列为1:2。阴极由Ca(10nm)/Al(100nm)层构成。
实施例5
DBP(T-DPP)2热稳定性能及其小分子光伏器件性能
DBP(T-DPP)2的热失重曲线图如图1所示。其分解温度为358℃。
DBP(T-DPP)2与PC71BM的混合比例为1:2(w/w,12mg/mL)下的J-V曲线图如图2所示。在该条件下，器件的短路电流为4.31mA/cm2，开路电压为0.79V，填充因子为29.45％，光伏效率为1.0％。
DBP(T-DPP)2与PC71BM的混合比例为1:2(w/w,12mg/mL)下EQE曲线图如图3所示。该图显示的EQE测试范围为300-800nm，在440nm处有最大EQE值，为42.33％。
DBP(T-DPP)2与PC71BM的混合比例为1:2(w/w,12mg/mL)时单电子器件的J1/2-V曲线如图4所示，其空穴迁移率最大为2.03×10-6cm2 V-1s-1。
尽管结合了优选实施例对本发明进行了说明，但本发明并不局限于上述实施例，应当理解所附权利要求概括了本发明的范围。在本发明构思的指导下，本领域的技术人员应当意识到，对本发明的各实施例方案所进行的一定的改变，都将被本发明的权利要求书的精神和范围所覆盖。
Claims (9)
1.以还原橙1为中心核的A-D-A型有机小分子光伏材料，其特征在于，其有机小分子共轭化合物的结构式为式I所示：
其中，R1独立的为C1～C20烷基；4-烷基苯基；5-烷基噻吩基或5-烷硫基噻吩基；
其中，拉电子桥联基团A选用下列结构之一：
其中，R独立的为C1～C20烷基。
2.根据权利要求1所述的以还原橙1为中心核的A-D-A型有机小分子光伏材料，其特征在于，该类材料以染料还原橙1衍生物为给体单元D，吡咯并吡咯二酮衍生物为受体单元A，并以烷基链进行修饰，利用该A-D-A型结构有机小分子光伏材料，通过溶液加工，制作有机小分子光伏器件。
3.根据权利要求1所述的以还原橙1为中心核的A-D-A型有机小分子光伏材料，其特征在于，具有吸电子性质桥联受体A单元为苯并噻二唑、单氟苯并噻二唑、双氟苯并噻二唑、双噻吩苯并噻二唑、双噻吩单氟苯并噻二唑、苯并噁二唑、单氟苯并噁二唑、双氟苯并噁二唑、双噻吩苯并噁二唑、双噻吩单氟苯并噁二唑、苯并三氮唑、单氟苯并三氮唑、双氟苯并三氮唑、双噻吩苯并三氮唑、双噻吩单氟苯并三氮唑、噻吩吡咯并吡咯二酮、噻唑吡咯并吡咯二酮、吡啶吡咯并吡咯二酮、苯基吡咯并吡咯二酮、苯基异靛蓝、噻吩基异靛蓝、噻唑基异靛蓝、噻吩[3,4-b]并-3-氟-噻吩酯、噻吩[3,4-b]并-3-氟-噻吩酮、噻吩[3,4-b]并-3-氟-噻吩酮、噻吩[3,4-b]并-3-噻吩酮、噻吩[3,4-b]并吡咯二酮、双噻吩-噻吩[3,4-b]并吡咯二酮、双噻吩[4,5-b]并吡啶酮并苯、双噻吩[3,4-b]并环己基二酮。
4.根据权利要求1～3任一项所述的以还原橙1为中心核的A-D-A型有机小分子光伏材料，其特征在于，实现了以染料还原橙1为起始原料构筑成A-D-A型结构光伏材料的太阳能电池光电转换，可以作为活性层应用于有机太阳能电池、有机场效应晶体管、有机电致发光二极管和有机近红外光电探测器器件中。
5.权利要求1～3任一项所述的还原橙1为中心核的A-D-A型有机小分子光伏材料，其特征在于，将A-D-A型共轭化合物与PC71BM共混作为光伏器件的活化层，实现小分子光伏器件器件的能量转换。
6.根据权利要求5所述的以还原橙1为中心核的A-D-A型有机小分子光伏材料，其特征在于，A-D-A型共轭化合物与PC71BM共混质量比为1:2。
7.根据权利要求5所述的还原橙1为中心核的A-D-A型有机小分子光伏材料，其特征在于，所述的小分子光伏器件的阳极修饰层为聚二氧乙基噻吩涂层。
8.根据权利要求4所述的以还原橙1为中心核的A-D-A型有机小分子光伏材料，其特征在于，活性层的厚度介于20纳米～1000纳米之间。
9.基于权利要求4所述的以还原橙1为中心核的A-D-A型有机小分子光伏材料，其特征在于，所述的活性层是通过溶液加工法实现，包括旋涂、刷涂、喷涂、浸涂、辊涂、丝网印刷、印刷或喷墨打印方法；其中所用溶剂为有机溶剂。
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| JP2008227245A (ja) * | 2007-03-14 | 2008-09-25 | Mitsui Chemicals Inc | 有機トランジスタ |
| KR20130090726A (ko) * | 2012-02-06 | 2013-08-14 | 주식회사 엘지화학 | 질소원소를 함유한 헤테로고리 유도체 및 이를 이용한 유기 전자 소자 |
| WO2015020572A1 (en) * | 2013-08-08 | 2015-02-12 | Lanxess Deutschland Gmbh | Conjugated polymers |
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| JP2008227245A (ja) * | 2007-03-14 | 2008-09-25 | Mitsui Chemicals Inc | 有機トランジスタ |
| KR20130090726A (ko) * | 2012-02-06 | 2013-08-14 | 주식회사 엘지화학 | 질소원소를 함유한 헤테로고리 유도체 및 이를 이용한 유기 전자 소자 |
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| CN114957237A (zh) * | 2022-01-02 | 2022-08-30 | 东华理工大学 | 一种以烷基修饰的还原橙3为中心核的D(A-Ar)2型有机小分子的合成及应用 |
| CN114957237B (zh) * | 2022-01-02 | 2024-02-02 | 东华理工大学 | 一种以烷基修饰的还原橙3为中心核的D(A-Ar)2型有机小分子的合成及应用 |
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