CN114989203B - 一种d-a型bodipy小分子非富勒烯太阳能电池受体的制备及其应用 - Google Patents
一种d-a型bodipy小分子非富勒烯太阳能电池受体的制备及其应用 Download PDFInfo
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Abstract
本发明涉及一种D‑A型BODIPY小分子非富勒烯太阳能电池受体的制备及其应用,采用meso位为强吸电子基三氟甲基(‑CF3)的BODIPY母体分别与4‑二苯胺基苯甲醛和9‑丁基‑9H‑咔唑‑3‑甲醛在对甲苯磺酸和哌啶催化作用下发生Knoevenagel缩合反应合成得到化合物CF3‑BODIPY‑1和CF3‑BODIPY‑2。在BODIPY母体上引入二苯胺基苯乙烯基或咔唑基团,不仅可以增强分子内电荷转移,调节能隙,进一步扩宽光谱吸收范围,使其移动到近红外区,还可以增加其光捕获效率,CF3‑BODIPY‑1和CF3‑BODIPY‑2均显示出窄带能隙,有利于提高器件光电转换性能。本发明不仅反应步骤简单、反应条件温和、合成成本低;将其作为活性层电子受体材料用于有机太阳能电池中获得了很好的效果,光电转化效率分别达到9.89%和13.07%,在有机太阳能电池领域中具有很好的应用前景。
Description
技术领域
本发明属于有机化合物合成、有机太阳能电池和精细化工技术领域,具体涉及一种D-A型BODIPY小分子非富勒烯太阳能电池受体的制备及其应用。
背景技术
面对日益严峻的能源危机和环境问题,需要开发太阳能、风能等清洁可再生能源。太阳能电池是一种直接将太阳能转化为电能的光伏技术。利用有机半导体材料的光伏原理,可以将来自太阳的光子能量转换为电能。基于体异质结(BHJ)活性层的有机太阳能电池(OSC)作为太阳能电池的重要组成部分,是一种很有前途的光伏技术,其具有许多独特的优势,如颜色可调、重量轻、材料来源广、制造成本低、在柔性基板上大面积制造等,因而受到研究者的广泛关注。在开发基于OSC的BHJ活性层的早期阶段,该活性层由聚合物或小分子供体和富勒烯受体混合而成,作为吸光活性层,其能量转换效率超过10%。然而,富勒烯受体材料的一些固有缺点限制了有机太阳能电池性能的进一步提高,包括弱光吸收和可见光区域利用不足、制备和纯化困难、合成成本高,能级调节差等。因此,开发新的电子受体材料取代富勒烯衍生物已成为有机太阳能电池研究领域的新热点。在这方面,与富勒烯基受体材料相比,非富勒烯小分子受体(NFSMA)由于其合成成本低、在可见光区域有强吸收、更高的稳定性、易于调节的能级以及更高的开路电压而显现出巨大的优势。然而,目前大部分有机非富勒烯小分子受体通常合成步骤多、难度大,导致总产率低,合成成本高,不利于未来的大规模商业应用。因此,开发易于合成和具有高光伏性能的新型NFSMA具有重要的科学意义。
氟硼二吡咯甲川类(BODIPY)染料是一类多功能荧光团,具有许多优异性质,如较高的荧光量子产率、较大的摩尔消光系数、良好的光稳定性和热稳定性、较低的光学带隙和优异的氧化还原性等。此外,通过在BODIPY的不同位点引入适当的电子给体和电子受体,可以很好地调节其光物理和电化学特性。此外,BODIPY染料通常具有较深的HOMO能级,从而导致高开路电压(Voc)。BODIPY优越的光物理和电化学性能使其在有机太阳能电池领域具有广泛的应用前景。
本发明涉及一种D-A型BODIPY小分子非富勒烯太阳能电池受体的制备及其应用,采用meso为三氟甲基(-CF3)的BODIPY母体分别与4-二苯胺基苯甲醛和9-丁基-9H-咔唑-3-甲醛在对甲苯磺酸和哌啶催化作用下发生Knoevenagel缩合反应合成化合物CF3-BODIPY-1和CF3-BODIPY-2。由于咔唑和三苯胺(TPA)基团具有强给电子能力、低氧化还原电位和高空穴迁移率,因而可以增强分子内电荷转移,调节能隙差,进一步扩宽光谱响应范围,使其红移到近红外区,另外,还可以增加光吸收能力,从而有利于提高器件性能。本发明的合成方法不仅反应步骤简单、反应条件温和、选择性较好,而且合成成本低;将其作为活性层电子受体用于有机太阳能电池中获得了很好的效果,光电转化效率最高可达到13.07%,在有机太阳能电池显示出优越的应用前景。
发明内容
发明目的:针对现有技术中存在的不足,本发明的目的是提供一种D-A型BODIPY小分子非富勒烯太阳能电池受体。本发明的另一目的是提供一种D-A型BODIPY小分子非富勒烯太阳能电池受体的制备及其应用。
技术方案:为了实现上述发明目的,本发明采用的技术方案为:
本发明的一种D-A型BODIPY小分子非富勒烯太阳能电池受体CF3-BODIPY-1和CF3-BODIPY-2,其特征在于,其结构式如下所示:
一种D-A型BODIPY小分子非富勒烯太阳能电池受体的制备,步骤如下:
1)在无水条件下,在圆底烧瓶中加入1,3,5,7-四甲基-8-三氟甲基-氟硼二吡咯(CF3-BODIPY)、4-二苯胺基苯甲醛或9-丁基-9H-咔唑-3-甲醛和新干燥过的对甲苯磺酸,并配备Dean-Stark装置,然后用甲苯溶解,并加入1mL哌啶作催化剂,搅拌加热到回流反应6~10小时;其中,CF3-BODIPY和4-二苯胺基苯甲醛或9-丁基-9H-咔唑-3-甲醛的摩尔比为1∶2.0~2.6。
2)将反应物冷至室温,用二氯甲烷稀释、水洗,经无水硫酸钠干燥,有机层减压蒸馏除去有机溶剂,残留物经硅胶柱层析分离,洗脱离剂为100%二氯甲烷,分别得到固体产物CF3-BODIPY-1和CF3-BODIPY-2。
一种D-A型BODIPY小分子非富勒烯太阳能电池受体,具体化学反应式如下:
一种D-A型BODIPY小分子非富勒烯太阳能电池受体的应用,步骤如下:
1)制备D-A型BODIPY小分子非富勒烯太阳能电池受体CF3-BODIPY-1、CF3-BODIPY-2薄膜,测得薄膜的电子吸收光谱及荧光发射光谱,选取光谱互补的宽带隙聚合物PBDB-T作为供体,其中供体PBDB-T结构如下所示:
2)有机太阳能电池器件的制备:器件是用氧化铟锡(ITO)/聚乙氧基噻吩(PEDOT)∶聚苯乙烯磺酸(PSS)(40nm)/活性层/聚芴衍生物(PFN)(20nm)/Al(50nm)构造而成,其中活性层是供体宽带隙聚合物PBDB-T和受体CF3-BODIPY-1或CF3-BODIPY-2的共混层,其光伏性能最佳的共混质量比为PBDB-T∶受体=1∶1.4。
本发明的有益效果
与现有技术相比,本发明的一种D-A型BODIPY小分子非富勒烯太阳能电池受体的制备及其应用具有的优点有:(1)该类D-A型BODIPY小分子非富勒烯太阳能电池受体反应步骤简单、反应条件温和、选择性较好,合成成本低;(2)该类D-A型BODIPY小分子非富勒烯太阳能电池受体具有良好的光热稳定性和高的开路电压等优异性质;(3)该类D-A型BODIPY小分子非富勒烯太阳能电池受体具有良好的光伏性能,光电转化效率最高分别达到9.89%和13.07%,使得其在太阳能电池中有很好的应用前景。
附图说明
图1是化合物CF3-BODIPY-1的高分辨质谱图;
图2是化合物CF3-BODIPY-2的高分辨质谱图;
图3是化合物CF3-BODIPY-1、CF3-BODIPY-2和PBDB-T的薄膜-电子吸收光谱图;
图4是化合物CF3-BODIPY-1、CF3-BODIPY-2和PBDB-T的薄膜-荧光发射光谱图;
图5光电转化效率电流-电压曲线。
具体实施方式
下面结合具体附图对本发明做进一步的说明。
检测所用仪器为:用1H-NMR、HRMS表征并证实D-A型BODIPY小分子非富勒烯太阳能电池受体的结构。检测所用仪器为:Bruker ARX400/600型核磁共振仪(TMS为内标,氘代氯仿为溶剂)岛津UV-3100型紫外-可见分光光度计(扫描范围300~900nm,光路狭缝2nm),荧光光谱用美国Amico Bowman Series 2 Luminescence Spectrometer测试,器件光电转换效率用Keithley 2400 source meter(AM1.5G,100mW/cm2)测试。
实施例1
圆底烧瓶中配备有Dean-Stark装置,将化合物CF3-BODIPY(50mg,0.16mmol),4-二苯胺基苯甲醛(109mg,0.4mmol)和新干燥的对甲苯磺酸(28mg)溶于25mL甲苯和1mL哌啶,混合物加热回流8小时,冷至室温,用二氯甲烷稀释、水洗,有机层用无水硫酸钠干燥,减压蒸除有机溶剂,残余物经硅胶柱层析分离提纯,洗脱剂为(100%CH2Cl2),得到固体化合物CF3-BODIPY-1(56mg,40%)。1H NMR:(DMSO-d6,600MHz,ppm):δ7.65(d,J=16.2Hz,2H),7.52(d,J=9.0Hz,4H),7.39(dd,J=18.0,10.8Hz,10H),7.25(s,2H),6.95(d,J=8.4Hz,4H),7.17(t,J=7.2Hz,4H),7.13(d,J=7.8Hz,8H),2.32(d,J=2.4Hz,6H)。ESI-HRMS:calculatedfor C52H40BF5N4:826.3266;found:826.3261[M]+。
实施例2
圆底烧瓶中配备有Dean-Stark装置,将化合物CF3-BODIPY(50mg,0.16mmol),9-丁基-9H-咔唑-3-甲醛(100mg,0.44mmol)和新干燥的对甲苯磺酸(28mg)溶于25mL甲苯和1mL哌啶,混合物加热回流6小时,冷至室温,用二氯甲烷稀释、水洗,有机层经无水硫酸钠干燥,减压蒸除有机溶剂,残余物经硅胶柱层析分离提纯,洗脱剂为(100%CH2Cl2),得到固体化合物CF3-BODIPY-2(69mg,56%)。1H NMR:(CDCl3,600MHz,ppm):δ8.35(s,2H),8.21(d,J=7.8Hz,2H),7.86-7.82(m,4H),7.57(d,J=16.2Hz,2H),7.51(t,J=7.8Hz,2H),7.43(d,J=7.2Hz,4H),7.30(t,J=7.2Hz,2H),6.88(s,2H),4.33(t,J=7.2Hz,4H),0.98(t,J=7.2Hz,6H),1.46-1.41(m,4H),1.55(s,6H),1.91-1.86(m,4H)。ESI-HRMS:calculated forC48H44BF5N4:782.3579;found:782.3562[M]+。
实施例3 D-A型BODIPY小分子非富勒烯太阳能电池受体CF3-BODIPY-1、CF3-BODIPY-2和PBDB-T的薄膜电子吸收光谱图
将化合物CF3-BODIPY-1、CF3-BODIPY-2和PBDB-T分别溶于氯仿溶液旋涂制备成薄膜,测定其薄膜电子吸收光谱。图3为D-A型BODIPY小分子非富勒烯太阳能电池受体CF3-BODIPY-1、CF3-BODIPY-2和PBDB-T的薄膜电子吸收光谱图。
实施例4 D-A型BODIPY小分子非富勒烯太阳能电池受体CF3-BODIPY-1、CF3-BODIPY-2及各自与PBDB-T混合后的薄膜荧光发射光谱图
将化合物CF3-BODIPY-1、CF3-BODIPY-2分别溶于氯仿溶液旋涂制备成薄膜同时与PBDB-T混合制备成薄膜,测定其薄膜荧光发射光谱。图4为D-A型BODIPY小分子非富勒烯太阳能电池受体CF3-BODIPY-1、CF3-BODIPY-2及各自与PBDB-T混合后的薄膜-荧光发射光谱图。
实施例5
本发明中以宽带隙聚合物PBDB-T为电子供体,并分别以D-A型BODIPY小分子CF3-BODIPY-1和CF3-BODIPY-2为非富勒烯太阳能电池受体制备成有机太阳能电池,分别测试器件的光电转化效率电流-电压曲线见图5。上述器件的性能总结如下表:
Claims (2)
1.一种D-A型BODIPY小分子非富勒烯太阳能电池受体在制备有机太阳能电池器件中的应用,其特征在于,有机太阳能电池器件是用氧化铟锡ITO/聚乙氧基噻吩PEDOT:聚苯乙烯磺酸PSS(40nm)/活性层/聚芴衍生物PFN(20nm)/Al(50nm)的结构制造的;活性层是宽带隙聚合物PBDB-T和受体CF3-BODIPY-1或CF3-BODIPY-2的共混层,其共混质量比为PBDB-T∶受体=1∶1.4;
2.根据权利要求1的应用,其特征在于,有机太阳能电池器件的光电转化效率分别为9.89%和13.07%。
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Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101565554A (zh) * | 2009-05-24 | 2009-10-28 | 大连理工大学 | 一类含有咔唑结构的强荧光氟硼二吡咯染料 |
CN107903282A (zh) * | 2017-11-29 | 2018-04-13 | 黄河科技学院 | 苯基乙烯基‑bodipy衍生物及其制备方法 |
CN112194787A (zh) * | 2020-09-11 | 2021-01-08 | 中国科学院化学研究所 | 具有近红外二区光响应性可降解共聚物制备方法与应用 |
CN113501836A (zh) * | 2021-07-28 | 2021-10-15 | 南京林业大学 | 一种星型bodipy近红外荧光染料及其制备方法 |
CN114315880A (zh) * | 2021-12-28 | 2022-04-12 | 南京林业大学 | 一类基于氟硼配合物的近红外二区荧光和光声双模态成像试剂 |
-
2022
- 2022-06-10 CN CN202210658840.1A patent/CN114989203B/zh active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101565554A (zh) * | 2009-05-24 | 2009-10-28 | 大连理工大学 | 一类含有咔唑结构的强荧光氟硼二吡咯染料 |
CN107903282A (zh) * | 2017-11-29 | 2018-04-13 | 黄河科技学院 | 苯基乙烯基‑bodipy衍生物及其制备方法 |
CN112194787A (zh) * | 2020-09-11 | 2021-01-08 | 中国科学院化学研究所 | 具有近红外二区光响应性可降解共聚物制备方法与应用 |
CN113501836A (zh) * | 2021-07-28 | 2021-10-15 | 南京林业大学 | 一种星型bodipy近红外荧光染料及其制备方法 |
CN114315880A (zh) * | 2021-12-28 | 2022-04-12 | 南京林业大学 | 一类基于氟硼配合物的近红外二区荧光和光声双模态成像试剂 |
Non-Patent Citations (2)
Title |
---|
Carbazole-based green and blue-BODIPY dyads and triads as donors for bulk heterojunction organic solar cells;Jian Yang 等;Dalton Trans.;5606-5617 * |
Systematic elongation of thienyl linkers and their effect on optical and electrochemical properties in carbazole-BODIPY donor-acceptor systems;Alina Brzeczek 等;RSC Adv.;36500-36509 * |
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