CN113265043B - 一种含引达省四酮的共轭聚合物及其在有机电子器件中的应用 - Google Patents
一种含引达省四酮的共轭聚合物及其在有机电子器件中的应用 Download PDFInfo
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Abstract
本发明公开一种含引达省四酮的共轭聚合物及其在有机电子器件中的应用。所述含引达省四酮的共轭聚合物，具有如下所示的结构：
其中，n为1‑100间的整数，A1、A2为相同或不同的共轭单元，C为共轭单元。引达省四酮具有四个吸电子性的羰基，能够增强聚合物主链的电负性，起到传输电子的作用。此外，羰基减少了电子在整个共轭主链的离域性，能够实现中宽带隙光学吸收的目的。以引达省四酮为缺电子单元的共轭聚合物能够在有机电子器件领域(包括聚合物太阳能电池、n型场效应晶体管、钙钛矿太阳能电池、有机热电器件及有机光探测器)得到应用。
Description
技术领域
本发明涉及聚合物材料领域，尤其涉及一种含引达省四酮的共轭聚合物及其在有机电子器件中的应用。
背景技术
近年来，通过低成本的技术手段使用清洁能源引起越来越多的关注，有机太阳能电池(OSCs)因其制备简易、柔性以及可大规模加工的优势应运而生。相比于无机硅太阳能电池，有机太阳能电池材料来源广泛、种类丰富，光电性能易于调控，其溶液加工性可助力实现低成本、大规模地制备柔性大面积器件，在应用场景方面与无机半导体太阳能电池形成优势互补，因而展现出巨大的商业开发价值和市场竞争力。
自2015年以来，有机太阳能电池取到了迅猛的发展，器件的最高光伏效率近来已达到17-18％(Sci.Bull.2020,65,272；Natl.Sci.Rev.2020,7,1239)。这主要得益于新型的非富勒烯受体出现打破了富勒烯受体长期统治有机光伏领域的瓶颈。非富勒烯受体由于可见-近红外区域宽吸收光谱、电子能级易于调节以及合成成本便宜等优势为有机太阳能电池技术赋予了更多可能性。作为一支重要的OSCs，由聚合物给体和聚合物受体共混作为活性层的全聚合物太阳能电池具有更优异的机械性能、光/热稳定性以及更好的成膜性，由此，也引起了科学家们的广泛关注。
尽管目前国内外多个课题组已经实现了高性能的全聚合物太阳能电池，但相对于小分子非富勒烯太阳能电池以及极具竞争力的钙钛矿太阳能电池技术、CIGS和CdTe太阳能电池等仍然落后(Adv.Mater.2020,32,2005942；Nano Energy 2020,72,104718；J.Am.Chem.Soc.2021,143,2665.)。目前存在的主要问题之一在于，高效聚合物受体材料较为匮乏，光电性能较为单一，限制了全聚合物太阳能电池多样化的发展。典型地，为了实现更高的光电流和光伏效率，高效的窄带隙聚合物受体，如芳香酰亚胺类聚合物受体(如N2200，Energy Environ.Sci.,2017,10,1243)和可聚合小分子受体聚合物(Angew.Chem.Int.Ed.,2017,56,13503.)等应用而生并得到快速发展。但是诸如中宽带隙的聚合物受体材料较少，仅有B-N类聚合物受体(CN105542131A、CN110229316A)稍微突出，但性能仍然有很大提升空间。作为聚合物受体的重要一方面，发展中宽带隙受体材料并以此制备高开路电压的高效电池器件，对于制备更高性能的三元器件和叠层器件以及室内弱光环境下的光伏应用具有重要意义。
高性能的聚合物受体材料离不开缺电子受体结构单元的设计和应用。如刘俊等通过硼化学桥联芳环设计新型B-N类受体，使器件效率从0.085％提升至超过10％(Chem.Mater.2020,32,3,1308.)。郭旭岗等将应用于场效应晶体管的缺电子单元二氰基苯并噻二唑构筑聚合物受体材料，也制备了相对高效的光伏器件，开拓了高效受体材料的新类型(Adv.Mater.2019,31,1905161.)。本发明涉及的聚合物受体材料是含有引达省四酮的中等带隙共轭聚合物。当前文献中引达省四酮单元应用于有机多孔聚合物(CN 112574407A、CN 112574395 A、CN 109265657 A等)、制备光伏给/受体小分子(Adv.Funct.Mater.2014,24,4645-4653；Thin Solid Films 2015,583,34-39；WO 2011/105624 Al.)、非线性光学材料(Proceedings of SPIE 2013,8827.)，但是用来制备共轭聚合物并将其应用于有机电子器件领域尚未见报道。
发明内容
鉴于上述背景技术中高效中宽带隙聚合物受体短缺的问题，本发明的目的在于提供一种含引达省四酮的共轭聚合物及其在有机电子器件中的应用。引达省四酮具有四个吸电子性的羰基，能够增强聚合物主链的电负性，起到传输电子的作用。此外，羰基减少了电子在整个共轭主链的离域性，能够实现中宽带隙光学吸收的目的。以引达省四酮为缺电子单元的共轭聚合物能够在有机电子器件领域(包括聚合物太阳能电池、n型场效应晶体管、钙钛矿太阳能电池、有机热电器件及有机光探测器)得到应用。
本发明的技术方案如下：
本发明的第一方面，提供一种含引达省四酮的共轭聚合物，其中，具有如下所示的结构：
其中，n为1-100间的整数，A1、A2为相同或不同的共轭单元，C为共轭单元。
本发明中，引达省四酮结构衍生于小分子给/受体材料中广泛使用的1,3-茚满二酮。具有双亚甲基的引达省四酮具有大的共轭平面和缺电子性，赋予其优异的电子传输能力，主链羰基减小了电子的离域性，有助于实现中宽带隙吸收的目的。此外，所述的含引达省四酮的共轭聚合物能够应用于包含有机太阳能电池、有机场效应晶体管、钙钛矿太阳能电池、热电器件及有机光探测器在内的有机电子器件中。
可选地，A1、A2独立地选自以下结构中的一种：
其中，R1为C1～C30的烷基或C1～C30的烷基上一个或多个碳原子被氧原子、硫原子、烯基、炔基、芳基和酯基中的至少一种官能团取代，X为氧原子、硫原子或硒原子。
可选地，C选自如下共轭单元中的一种：
其中，X为氧原子、硫原子或硒原子；R2为C1～C30的烷基或C1～C30的烷基上一个或多个碳原子被氧原子、硫原子、烯基、炔基、芳基和酯基中的至少一种官能团取代；R3为氢原子、氟原子、氯原子、氰基或C1～C30的烷基或C1～C30的烷基上多个碳原子被氧原子、硫原子、烯基、炔基、芳基和酯基中的至少一种官能团取代。
本发明的第二方面，提供本发明所述的含引达省四酮的共轭聚合物在有机电子器件中的应用。
本发明的第三方面，提供一种有机电子器件，其中，包含如本发明所述的含引达省四酮的共轭聚合物。
可选地，所述有机电子器件选自有机太阳能电池、有机场效应晶体管、钙钛矿太阳能电池、有机热电器件及有机光探测器中的一种。
与现有技术相比，本发明的主要优势包括以下几点：
(1)本发明中的含引达省四酮的共轭聚合物具有合成简易，制备成本低廉的优势。具体体现在，制备原料廉价，合成仅需三步且无需复杂的柱层析分离，能够实现材料低成本制备之优势。
(2)引达省四酮衍生于母体1,3-茚满二酮单元，具有两个亚甲基反应官能团和更大的共轭平面，可以方便地开发出迁移率更高的共轭聚合物，用于有机电子器件。
(3)引达省四酮单元的羰基减少了共轭主链上电子的离域性，有助于实现中宽带隙吸收之目的，能够制备具有高开路电压的高效太阳能电池器件。
附图说明
图1为聚合物P1的GPC曲线。
图2为聚合物P2的GPC曲线。
图3为聚合物P3的GPC曲线。
图4为聚合物P4的GPC曲线。
图5为聚合物P4a的GPC曲线。
图6为聚合物P5的GPC曲线。
图7为聚合物P6的GPC曲线。
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，其目的在于帮助更好地理解本发明的内容，具体包括材料的制备合成、表征与相应有机电子器件的制备和测试，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。
以下实施例中，除非另行说明，否则所有试剂都是商业渠道获得的。其中，化合物5、5a和化合物11通过文献报道的方法制备得到(Chem.Mater.,2015,27,4719；Adv.Funct.Mater.,2016,26,6876；ACS Appl.Mater.Interfaces,2017,9,7315.)。
实施例1
含引达省四酮的共轭聚合物P1的合成路线如下：
(1)化合物4的合成
将均苯四甲酸酐(23mmol,5g)、乙酰乙酸乙酯(69mmol,8.94g)、三乙胺(275mmol,12 27.8g)溶于乙酸酐(80mL)中，100℃下加热2小时，然后将反应液放于3℃的冰箱里冷却24小时得到含有固体沉淀的混合物。将固体过滤后并用少量乙酸酐和乙醚洗涤得到中间体2。将得到的中间体2溶于水中并在冰浴下用H2SO4酸化析出固体。然后将反应液过滤，乙醇洗涤固体，放于通风橱中常温干燥24小时，并用油泵抽滤除掉残余水分得到化合物3。在化合物3中加入大量无水乙腈，回流搅拌3小时后，待冷却至室温，将固体过滤，并用乙腈重结晶，得到关键中间体4。重量900mg，产率为18％。1H NMR(500M,CDCl3)δ8.54(s,2H),3.45(s,4H)。
(2)化合物6的合成
将制得的中间体4(2.76mmol,0.59g)和化合物5(6.36mmol,3g)溶于135mL冰乙酸中回流48小时。待冷却至室温时，将反应液倒入水中，用二氯甲烷萃取、水洗并用无水硫酸钠干燥。使用旋转蒸发仪移除掉溶剂后，用二氯甲烷/丙酮混合溶剂重结晶得到黄色的化合物6。重量2.48g，产率79％。1H NMR(500MHz,CDCl3)δ8.42(s,2H),7.93(s,2H),7.62(s,2H),2.56(d,4H),1.73–1.64(m,2H),1.31–1.18(m,64H),0.91–0.79(m,12H)。
(3)共轭聚合物P1的合成
将制得的化合物6(0.1mmol,112.1mg)、双锡单体7(0.1mmol,90.5mg)以及催化剂Pd2(dba)3(0.003mmol,2.7mg)和配体P(o-tol)3(0.024mmol,7.3mg)在氩气气氛下溶于4mL无水无氧氯苯(CB)中，并将该反应液在80℃下搅拌反应2小时。将反应液滴入150mL甲醇中得到蓝色絮状沉淀，并进一步过滤，通过索式提取器依次用甲醇、正己烷、二氯甲烷、氯仿和氯苯抽提除掉杂质和低分子量组份。将氯苯相的溶液浓缩并在100mL甲醇中沉淀、过滤，即得到目标聚合物P1，重量60mg，产率38％。GPC:数均分子量(Mn)＝41.2kDa，多分散指数(PDI)＝1.98(如图1)。Anal.Calcd for(C96H130O4S6)n(％):C,74.85；H,8.51；Found(％):C,74.96；H,8.71。
实施例2
实施例1中已给出化合物6的合成方法，实施例2中聚合物P2由同上类似方法得到，合成路线如下：
将制得的化合物6(0.1mmol,112.1mg)、双锡单体8(0.1mmol,94.1mg)以及催化剂Pd2(dba)3(0.003mmol,2.7mg)和配体P(o-tol)3(0.024mmol,7.3mg)在氩气气氛下溶于4mL无水无氧氯苯中，并将该反应液在80℃下搅拌反应1.8小时。随后，将反应液滴入150mL甲醇中并将得到的蓝色沉淀物过滤，进一步通过索式提取器依次用甲醇、正己烷、二氯甲烷、氯仿和氯苯抽提除掉杂质和低分子量组份。将氯苯相的溶液浓缩并在100mL甲醇中沉淀，过滤，即得到目标聚合物P2，重量86mg，产率54％。GPC:Mn＝25.4kDa，PDI＝1.71(如图2)。Anal.Calcd for(C96H128F2O4S6)n(％):C,73.14；H,8.18；Found(％):C,73.30；H,8.48。
实施例3
实施例1中已给出化合物6的合成方法，实施例3中聚合物P3由同上类似方法得到，合成路线如下：
将制得的化合物6(0.1mmol,112.1mg)、双锡单体9(0.1mmol,97.3mg)以及催化剂Pd2(dba)3(0.003mmol,2.7mg)和配体P(o-tol)3(0.024mmol,7.3mg)在氩气气氛下溶于4mL无水无氧氯苯中，并将该反应液在80℃下搅拌反应1.6小时。随后，将反应液滴入150mL甲醇中并将得到的蓝色沉淀物过滤，进一步通过索式提取器依次用甲醇、正己烷、二氯甲烷、氯仿和氯苯抽提除掉杂质和低分子量组份。将氯苯相的溶液浓缩并在100mL甲醇中沉淀，过滤，即得到目标聚合物P3。重量82mg，产率50％。GPC:Mn＝27.0kDa，PDI＝2.88(如图3)。Anal.Calcd for(C96H128Cl2O4S6)n(％):C,71.65；H,8.02；Found(％):C,71.25；H,8.41。
实施例4
实施例1中已给出化合物6的合成方法，实施例4中聚合物P4由同上类似方法得到，合成路线如下：
将制得的化合物6(0.1mmol,112.1mg)、双锡单体10(0.1mmol,41.0mg)以及催化剂Pd2(dba)3(0.003mmol,2.7mg)和配体P(o-tol)3(0.024mmol,7.3mg)在氩气气氛下溶于4mL无水无氧氯苯中，并将该反应液在80℃下搅拌反应1小时。然后将该反应液滴入150mL甲醇中沉淀，并将颗粒状沉淀物过滤，进一步通过索式提取器依次用甲醇、正己烷、二氯甲烷、氯仿和氯苯抽提除掉杂质和低分子量组份。将氯苯相的溶液浓缩并在100mL甲醇中沉淀，过滤，即得到目标聚合物P4。重量64mg，产率61％。GPC:Mn＝7.0kDa,PDI＝2.11(如图4)。Anal.Calcd for(C66H92O4S3)n(％):C,75.81；H,8.87Found(％):C,75.59；H,8.99。
实施例5
实施例1中已给出化合物6的合成方法，实施例5中聚合物P4a由同上类似方法得到，合成路线如下：
将制得的化合物6(0.1mmol,112.1mg)、双锡单体10a(0.1mmol,44.6mg)以及催化剂Pd2(dba)3(0.003mmol,2.7mg)和配体P(o-tol)3(0.024mmol,7.3mg)在氩气气氛下溶于4mL无水无氧氯苯中，并将该反应液在80℃下搅拌反应45分钟。然后将该反应液滴入150mL甲醇中沉淀，并将颗粒状沉淀物过滤，进一步通过索式提取器依次用甲醇、正己烷、二氯甲烷、氯仿和氯苯抽提除掉杂质和低分子量组份。将氯苯相的溶液浓缩并在100mL甲醇中沉淀，过滤，即得到目标聚合物P4a。重量55mg，产率51％。GPC:Mn＝6.3kDa,PDI＝2.04(如图5)。Anal.Calcd for(C66H90F2O4S3)n(％):C,73.29；H,8.39 Found(％):C,73.01；H,8.52。
实施例6
含引达省四酮的共轭聚合物P5的合成路线如下:
(1)化合物6a的合成
将制得的化合物4(1.40mmol,0.30g)和化合物5a(6.36mmol,1.64g)溶于100mL冰乙酸中回流48小时。待冷却至室温时，将反应液倒入水中，用二氯甲烷萃取、水洗并用无水硫酸钠干燥。使用旋转蒸发仪移除掉溶剂后，用二氯甲烷/丙酮混合溶剂重结晶得到化合物6a。重量1.26g，产率75％。1H NMR(500MHz,CDCl3)δ8.38(s,2H),7.92(s,2H),7.56(s,2H),7.28(s,2H),2.79–2.72(d,8H),2.30–2.23(m,8H),1.63–1.17(m,36H),0.98–0.83(m,24H)。
(2)聚合物P5的合成
将制得的化合物6a(0.1mmol,119.7mg)、双锡单体10(0.1mmol,41.0mg)以及催化剂Pd2(dba)3(0.003mmol,2.7mg)和配体P(o-tol)3(0.024mmol,7.3mg)在氩气气氛下溶于4mL无水无氧氯苯中，并将该反应液在80℃下搅拌反应2小时。随后，将反应液滴入150mL甲醇中并将得到的蓝色沉淀物过滤，进一步通过索式提取器依次用甲醇、正己烷、二氯甲烷、氯仿和氯苯抽提除掉杂质和低分子量组份。将氯苯相的溶液浓缩并在100mL甲醇中沉淀，过滤，即得到目标聚合物P5。重量77mg，产率69％。GPC:Mn＝24.3kDa,PDI＝4.14(如图6)。Anal.Calcd for(C68H80O4S5)n(％):C,72.81；H,7.19；Found(％):C,72.88；H,7.02。
实施例7
实施例5中已给出化合物6a的合成方法，实施例7中聚合物P6由同上类似方法得到。
将制得的化合物6a(0.1mmol,119.7mg)、双锡单体11(0.1mmol,115.3mg)以及催化剂Pd2(dba)3(0.003mmol,2.7mg)和配体P(o-tol)3(0.024mmol,7.3mg)在氩气气氛下溶于4mL无水无氧氯苯中，并将该反应液在80℃下搅拌反应2小时。然后将该反应液滴入150mL甲醇中沉淀，并将沉淀物过滤，进一步通过索式提取器依次用甲醇、正己烷、二氯甲烷、氯仿和氯苯抽提除掉杂质和低分子量组份。将氯苯相的溶液浓缩并在100mL甲醇中沉淀，过滤，即得到目标聚合物P6。重量102mg，产率55％。GPC:Mn＝21.3kDa,PDI＝4.27(如图7)。Anal.Calcd for(C120H166O4S6)n(％):C,77.28；H,8.97；Found(％):C,77.01；H,9.10。
以实施例1-7中得到的共轭聚合物P1-P6为例说明此类聚合物作为活性层材料在有机太阳能电池中的应用。
实施例8
将对本发明中指出的含引达省四酮的共轭聚合物在有机太阳能电池的应用实例进行详细说明，但本发明不限于所列之例。
有机太阳能电池的制备及性能测试：
将购买到的氧化铟锡(ITO)玻璃分别依次用丙酮超声清洗10分钟；低浓度micro级洗涤剂超声清洗15分钟；超纯去离子水超声清洗3次，每次10分钟；色谱纯异丙醇超声清洗15分钟，经过清洗的ITO玻璃基片用氧气等离子处理5分钟待用。旋涂一层聚乙撑二氧噻吩：聚苯乙烯磺酸盐(PEDOT:PSS)，150℃下干燥15分钟，将实施例1-6中的含引达省四酮的共轭聚合物P1-P6作为受体材料分别与聚合物给体材料PBDB-T(重量比都为1:1.2)的共混溶液旋涂在PEDOT:PSS阳极界面层上制备活性层。在活性层上旋涂一层阴极界面层PFN-Br，在阴极界面层上蒸镀厚度为100nm的银电极作为阴极即得到有机太阳能电池，器件有效面积0.04cm2。
电池器件性能测试是在Oriel 91192型AM 1.5G太阳光模拟灯的照射下进行，辐射度为1000瓦特/平方米，使用Keithley 2400型数字源表测试电流-电压曲线，从而获得能量转换效率等关键参数。测试结果汇总于表1。表中的结果表明了含引达省四酮的共轭聚合物在制备具有高开路电压(VOC)的有机太阳能电池中的应用潜力。
表1
| 聚合物 | V<sub>OC</sub>(V) | J<sub>SC</sub>(mA cm<sup>-2</sup>) | FF | PCE(％) |
| P1 | 1.00 | 10.62 | 0.50 | 5.31 |
| P2 | 0.94 | 10.57 | 0.49 | 4.87 |
| P3 | 0.91 | 11.61 | 0.54 | 5.54 |
| P4 | 0.92 | 6.73 | 0.36 | 2.23 |
| P4a | 0.93 | 7.50 | 0.51 | 3.56 |
| P5 | 1.01 | 8.32 | 0.40 | 3.36 |
| P6 | 0.99 | 3.47 | 0.55 | 1.89 |
实施例中使用的材料PBDB-T和PFN-Br化学结构如下：
使用紫外-可见吸收光谱和循环伏安法测试材料的光学性能和电化学性质，关键光电性质参数如表2所示。结果表明，本发明实施例中的共轭聚合物材料具有中等到窄带隙的吸收、合适能级以及较好的电子迁移率，适合作为有机太阳能电池的受体材料。
表2
表2中λpeak film和λonset film分别指聚合物薄膜的最大吸收峰值和最大吸收带边；Egopt指聚合物薄膜的光学带隙，由公式Egopt＝1240/λonset film计算得到；EHOMO和ELUMO分别指聚合物薄膜的HOMO能级和LUMO能级；μe指电子迁移率。
应当理解的是，本发明的应用不限于上述的举例，对本领域普通技术人员来说，可以根据上述说明加以改进或变换，所有这些改进和变换都应属于本发明所附权利要求的保护范围。
Claims (4)
1.一种含引达省四酮的共轭聚合物，其特征在于，具有如下所示的结构：
其中，n为1-100间的整数，A1、A2为相同或不同的共轭单元，C为共轭单元；
其中，A1、A2独立地选自以下结构中的一种：
其中，R1为C1～C30的烷基或C1～C30的烷基上一个或多个碳原子被氧原子、硫原子、烯基、炔基、芳基和酯基中的至少一种官能团取代；X为氧原子、硫原子或硒原子；
其中，C选自如下共轭单元中的一种：
其中，X为氧原子、硫原子或硒原子；R2为C1～C30的烷基或C1～C30的烷基上一个或多个碳原子被氧原子、硫原子、烯基、炔基、芳基和酯基中的至少一种官能团取代；R3为氢原子、氟原子、氯原子、氰基或C1～C30的烷基或C1～C30的烷基上多个碳原子被氧原子、硫原子、烯基、炔基、芳基和酯基中的至少一种官能团取代。
2.权利要求1所述的含引达省四酮的共轭聚合物在有机电子器件中的应用。
3.一种有机电子器件，其特征在于，包含如权利要求1所述的含引达省四酮的共轭聚合物。
4.根据权利要求3所述的有机电子器件，其特征在于，所述有机电子器件选自有机太阳能电池、有机场效应晶体管、钙钛矿太阳能电池、有机热电器件及有机光探测器中的一种。
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