CN113666953A - 一类苯并噻二唑硼氮衍生物材料及其在有机电子器件的应用 - Google Patents
一类苯并噻二唑硼氮衍生物材料及其在有机电子器件的应用 Download PDFInfo
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Abstract
本发明公开了一类苯并噻二唑硼氮衍生物材料及其在有机电子器件的应用,所述R1和R2独立选自C6~C12烷基链,R3为氢、氟、氯、溴、碘或甲基中的任一种;一种如上所述的化合物在有机电子器件中的应用;一种有机电子器件,包含至少一种如上所述的化合物。一种苯并噻二唑硼氮衍生物,具有吸收波长位于长波长的红外吸收,其吸收光谱表现为具有宽的吸收范围,且具有高光电转化效率;此类苯并噻二唑硼氮衍生物制备得到的有机太阳能电池元件具有高的光电转化效率、及长的器件寿命;硼与氮具有相反的共振效应,相应的硼‑氮稠环化合物可提高分子三重态能级,但不影响其堆积成膜,降低复合损失,有效提高电池效率。
Description
技术领域
本发明涉及有太阳能技术领域,特别是涉及一种苯并噻二唑硼氮衍生物,混合物及组合物,及其在有机太阳能技术领域的应用。
背景技术
气候变化可以说是人类目前面临的最大挑战之一,在电力生产中以可持续能源代替化石燃料成为了解决这一问题的有效方式。硅太阳能电池在全球范围内的装机容量正在迅速增加,但是新一代太阳能电池技术也有可能在不久的将来作为一种可持续技术成熟,从而有助于这一转变。有机太阳能电池(Organic Solar Cells,OPV)由于其半透明、柔性可卷曲,轻质便于携带以及颜色和形状可设计性,已经被深入研究多年并开始尝试于市场应用。近几年,随着研究人员使用新型非富勒烯受体材料将实验室电池效率提升到15%以上,并且不断改进大面积电池制备工艺,采用成熟薄膜技术的大面积有机太阳能电池竞争力正在逐步提高,但是从实验室到制造工厂的挑战,仍然是实现市场化的最大障碍。
由于有机半导体材料在合成上具有多样性、制造成本相对较低,且具有优良的光学与电学性能,因此,由有机半导体材料制成的有机电子器件在太阳能技术领域应用方面具有很大的潜力。
目前有机太阳能电池效率提升的开发,非富勒烯受体材料的改进已成为最有效的方法。现有的小分子受体材料,因其组分的三重态能级比分子电荷转移态能级低太多,有大量三重态复合造成的非辐射损失,从而导致电池效率下降。传统的方法是引入重原子或者构建扭曲的分子结构以提高其三重态能级,减少与电荷转移态的能级差,但这样的方法同时也会影响分子成膜堆积,降低载流子迁移率,进而降低器件效率。为此,我们提出了一类苯并噻二唑硼氮衍生物材料及其在有机电子器件的应用。
发明内容
本发明的目的是提供一类苯并噻二唑硼氮衍生物材料及其在有机电子器件的应用,通过巧妙的分子设计,在苯并三氮唑结构基础上,合成了一系列具有合适能级的硼氮化合物受体材料,且具有很好的电子传输性能以及非常大的光谱吸收范围,通过质谱分析对它们的结构进行确认,并应用于有机电子器件。可以有效解决背景技术中提出的问题。
为实现上述目的,本发明采取的技术方案为:
一种如通式(I)所示的苯并噻二唑硼氮衍生物:
其中,
R1和R2独立选自C1~C20的烷基;
X1和X2独立的选自以下基团中的任意一种:
其中,
R3为氢、卤素或C1~C5烷基。
进一步地,所述R1和R2独立选自C6~C12烷基链。
优选地,所述R3为氢、氟、氯、溴、碘或甲基中的任一种。
一种如上所述的化合物在有机电子器件中的应用。
一种有机电子器件,包含至少一种如上所述的化合物。
进一步地,所述有机电子器件可选于有机光伏电池(OPV)、有机光电探测器(OPD)、有机发光二极管(OLED)、有机发光电池(OLEEC)、有机场效应管(OFET)、有机发光场效应管、有机激光器,有机自旋电子器件,有机传感器及有机等离激元发射二极管(OrganicPlasmon Emitting Diode)。
优选地,有机电子器件是太阳能电池器件,其至少包含有一活性层,所述的活性层包含有至少一种如上所述的化合物。
一、一种苯并噻二唑硼氮衍生物,具有吸收波长位于长波长的红外吸收,其吸收光谱表现为具有宽的吸收范围,且具有高光电转化效率;
二、此类苯并噻二唑硼氮衍生物制备得到的有机太阳能电池元件具有高的光电转化效率、及长的器件寿命;
三、硼与氮具有相反的共振效应,相应的硼-氮稠环化合物可提高分子三重态能级,但不影响其堆积成膜,降低复合损失,有效提高电池效率。
附图说明
图1是按照本发明所涉及的太阳能电池器件结构图。
图中:101、基板;102、阳极;103、空穴传输层(HTL);104、活性层;105、电子传输层(ETL);106、阴极。
具体实施方式
为使本发明实现的技术手段、创作特征、达成目的与功效易于明白了解,下面结合具体实施方式,进一步阐述本发明。
实施例1:化合物1的合成
向500mL二口瓶中加入1-1(6.04g,6mmol),1-2(3.22g,20mmol)以及5mL吡啶,然后抽通氩气三次,在氩气保护下加入250mL氯仿,在65℃反应24小时。冷却至室温,二氯甲烷萃取三次,合并有机相,干燥过滤并加硅胶旋干,柱层析(正己烷:二氯甲烷=3:1)分离纯化,得白色粉末3.18g,产率41%。MS(EI)m/z:[M]+:1292.35.
实施例2:化合物2的合成
将1-1(5.03g,5mmol),1-3(3.68g,16mmol)以及5mL吡啶加入500mL两口瓶,然后抽通氩气三次,在氩气保护下加入300mL氯仿,在65℃反应24小时。冷却至室温,二氯甲烷萃取三次,合并有机相,干燥过滤并加硅胶旋干,柱层析(正己烷:二氯甲烷=3:1)分离纯化,得白色粉末2.72g,产率38%。MS(EI)m/z:[M]+:1430.42.
实施例3:化合物3的合成
将1-1(6.03g,6mmol),1-4(5.04g,20mmol)以及5mL吡啶加入500mL两口瓶,然后抽通氩气三次,在氩气保护下加入300mL氯仿,在65℃反应24小时。冷却至室温,二氯甲烷萃取三次,合并有机相,干燥过滤并加硅胶旋干,柱层析(正己烷:二氯甲烷=3:1)分离纯化,得白色粉末3.27g,产率37%。MS(EI)m/z:[M]+:1474.43.
对比例:稠环苯并噻二唑基非富勒烯受体材料(Y6)的合成
在250ml圆底烧瓶中,将化合物2-1(0.154g,0.15mmol)和2-2(0.345g,1.50mmol)溶于45ml氯仿中,加入1ml吡啶,混合液在氩气保护下回流反应12小时,冷却至室温,倒入200ml无水甲醇中,抽滤得到粗产物,用硅胶柱层析分离提纯,得到深蓝色固体0.140g,产率64.3%。MS(EI)m/z:[M]+:1450.54.
有机太阳能电池器件的制备与表征
OPV器件制备采用商业化的给体聚合物PM6材料:
HTL:PEDOT:PSS;
给体(Donor):PM6
受体(Acceptor):实施例1-3、对比例制备所得化合物;
ETL:PFN-Br。
具有ITO/HTL(40nm)/Donor:Acceptor(1:1.2,150nm)/ETL(10nm)/Ag(100nm)的OPV器件的制备步骤如下:
a、导电玻璃基片的清洗:首次使用时,可用多种溶剂进行清洗,例如氯仿、酮、异丙醇进行清洗,然后进行紫外臭氧等离子处理;
b、PEDOT:PSS(40nm)在空气中涂布制备,并高温烘烤;
c、活性层(PM6:Acceptor)(150nm)、ETL(10nm)在手套箱(惰性气体氛围)中涂布烘烤而成。
d、阴极:Ag(100nm)在高真空(1×10-6毫巴)中热蒸镀而成;
e、封装:器件在氮气手套箱中用紫外线硬化树脂封装。
对制备出来的有机太阳能电池OPV器件进行性能测试,在太阳光模拟器(SS-F5-3A)AM 1.5G标准光照射下,测试电池电流-电压曲线,计算光电转换效率:
以上显示和描述了本发明的基本原理和主要特征和本发明的优点。本行业的技术人员应该了解,本发明不受上述实施例的限制,上述实施例和说明书中描述的只是说明本发明的原理,在不脱离本发明精神和范围的前提下,本发明还会有各种变化和改进,这些变化和改进都落入要求保护的本发明范围内。本发明要求保护范围由所附的权利要求书及其等效物界定。
Claims (7)
2.根据权利要求1所述的一种苯并噻二唑硼氮衍生物,其特征在于:所述R1和R2独立选自C6~C12烷基链。
3.根据权利要求1所述的一种苯并噻二唑硼氮衍生物,其特征在于:所述R3为氢、氟、氯、溴、碘或甲基中的任一种。
4.一种如权利要求1任一项所述的化合物在有机电子器件中的应用。
5.一种有机电子器件,包含一种如权利要求1任一项所述的化合物。
6.根据权利要求5所述的一种有机电子器件,其特征在于,所述有机电子器件可选于有机光伏电池(OPV)、有机光电探测器(OPD)、有机发光二极管(OLED)、有机发光电池(OLEEC)、有机场效应管(OFET)、有机发光场效应管、有机激光器,有机自旋电子器件,有机传感器或有机等离激元发射二极管(Organic Plasmon Emitting Diode)。
7.根据权利要求6所述的一种有机电子器件,其特征在于,所述有机电子器件为太阳能电池器件,其至少包含有一活性层,所述活性层包含有一种如权利要求1任一项所述的化合物。
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114621276A (zh) * | 2022-02-18 | 2022-06-14 | 广州追光科技有限公司 | 一种苯并噻二唑硼氮衍生物及其应用 |
CN114621275A (zh) * | 2022-02-18 | 2022-06-14 | 广州追光科技有限公司 | 一种苯并三氮唑硼氮衍生物及其应用 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109134513A (zh) * | 2018-09-10 | 2019-01-04 | 中南大学 | 一种稠环苯并噻二唑基非富勒烯受体材料及其制备方法和应用 |
WO2020143912A1 (en) * | 2019-01-09 | 2020-07-16 | MAX-PLANCK-Gesellschaft zur Förderung der Wissenschaften e.V. | Electrochemical device, batteries, method for harvesting light and storing electrical energy, and detection methods |
CA3159462A1 (en) * | 2019-11-26 | 2021-06-03 | Cubicpv, Inc. | 2d perovskite tandem photovoltaic devices |
CN113087725A (zh) * | 2021-04-06 | 2021-07-09 | 广州追光科技有限公司 | 一类苯并噻二唑氘代衍生物及其在有机电子器件的应用 |
CN113234094A (zh) * | 2021-04-02 | 2021-08-10 | 广州追光科技有限公司 | 苯并噻二唑衍生物及其在有机电子器件的应用 |
-
2021
- 2021-07-19 CN CN202110810600.4A patent/CN113666953B/zh active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109134513A (zh) * | 2018-09-10 | 2019-01-04 | 中南大学 | 一种稠环苯并噻二唑基非富勒烯受体材料及其制备方法和应用 |
WO2020143912A1 (en) * | 2019-01-09 | 2020-07-16 | MAX-PLANCK-Gesellschaft zur Förderung der Wissenschaften e.V. | Electrochemical device, batteries, method for harvesting light and storing electrical energy, and detection methods |
CA3159462A1 (en) * | 2019-11-26 | 2021-06-03 | Cubicpv, Inc. | 2d perovskite tandem photovoltaic devices |
CN113234094A (zh) * | 2021-04-02 | 2021-08-10 | 广州追光科技有限公司 | 苯并噻二唑衍生物及其在有机电子器件的应用 |
CN113087725A (zh) * | 2021-04-06 | 2021-07-09 | 广州追光科技有限公司 | 一类苯并噻二唑氘代衍生物及其在有机电子器件的应用 |
Non-Patent Citations (4)
Title |
---|
JUN YUAN,等: "Enabling low voltage losses and high photocurrent in fullerene-free organic photovoltaics", NATURE COMMUNICATIONS, vol. 10, no. 01, pages 570 * |
JUN YUAN,等: "Single-Junction Organic Solar Cell with over 15% Efficiency Using Fused-Ring Acceptor with Electron-Deficient Core", JOULE, vol. 03, no. 04, pages 1140 - 1151 * |
YI HAN,等: "Dual-responsive BN-embedded phenacenes featuring mechanochromic luminescence and ratiometric sensing of fluoride ions", J. MATER. CHEM. C, vol. 06, no. 39, pages 10456 - 10463 * |
刘俊,等: "含硼氮配位键的高分子电子受体材料", 高分子学报, no. 12, pages 1856 - 1869 * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114621276A (zh) * | 2022-02-18 | 2022-06-14 | 广州追光科技有限公司 | 一种苯并噻二唑硼氮衍生物及其应用 |
CN114621275A (zh) * | 2022-02-18 | 2022-06-14 | 广州追光科技有限公司 | 一种苯并三氮唑硼氮衍生物及其应用 |
CN114621275B (zh) * | 2022-02-18 | 2022-11-08 | 广州追光科技有限公司 | 一种苯并三氮唑硼氮衍生物及其应用 |
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