CN115073488A - 全稠环类有机光伏受体及其制备方法与应用 - Google Patents
全稠环类有机光伏受体及其制备方法与应用 Download PDFInfo
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- CN115073488A CN115073488A CN202110271944.2A CN202110271944A CN115073488A CN 115073488 A CN115073488 A CN 115073488A CN 202110271944 A CN202110271944 A CN 202110271944A CN 115073488 A CN115073488 A CN 115073488A
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- 125000003118 aryl group Chemical group 0.000 claims description 23
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 5
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
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- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
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- 238000006467 substitution reaction Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
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- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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Abstract
Description
技术领域
本发明属于有机光伏领域,具体涉及一种全稠环类有机光伏受体及其制备方法与应用。
背景技术
有机太阳能电池(OPV)是一种将光转化为电的新型薄膜太阳能电池技术。近年来,随着给体(D)-受体(A)型非富勒烯小分子受体的飞速发展,有机光伏器件的光电转化效率已经超过了17%。与此同时,效率、成本、稳定性这三个关键性要素受到了越来越多的重视。目前广泛研究的非富勒烯小分子受体通常具有一个富电子给体主核以及两个缺电子受体末端,给受体单元通过诺文格尔反应形成的双键相连。这类结构能级易于调节,具有较高的吸光系数及光电转化效率。但是,这类结构面临的最大问题在于稳定性方面:通过诺文格尔反应合成的非富勒烯小分子受体稳定性通常较差,尤其是单分子稳定性。该类受体的环外双键极易发生光氧化反应和/或亲核试剂参与的加成反应,制备成器件后氧化锌修饰层也会对受体的降解产生催化作用,从而导致光伏器件失效。这些影响稳定性的因素极大程度上限制了现有结构体系的进一步发展与商业化应用。因此,提高受体分子的稳定性已经成为了广大研究工作者的重要探索方向。我们以简化合成步骤、提高分子稳定性为出发点,设计合成了一系列全稠环分子,并且表征了其作为小分子受体在有机光伏领域的器件性能。该系列材料稳定性具有显著优势,更利于有机光伏的商业化推广。
发明内容
本发明提供一种式(I)所示的化合物:
其中,A选自无取代或任选被一个、两个或更多个R取代的C6-14芳环、5-14元杂芳环或稠环,所述稠环由两个或更多个C5-14烯烃环、5-14元杂环、C6-14芳环或5-14元杂芳环稠合形成;每个E相同或不同,彼此独立地选自S或Se;每个R相同或不同,彼此独立地选自C1-40烷基、C1-20烷基C6-14芳基;
根据本发明的实施方案,A选自无取代或任选被一个、两个或更多个R取代的苯环或稠环,所述稠环由两个或更多个环戊二烯、噻吩、吡咯、吡喃、吡嗪、噻二唑或苯稠合形成;每个R相同或不同,彼此独立地选自丁基、戊基、己基、庚基、辛基、壬基、癸基、2-乙基己基、2-己基癸基、2-辛基十二烷基、2-癸基十四烷基、4-己基苯基;
根据本发明的实施方案,A选自以下结构;其中E和R具有上文所述的定义:
根据本发明的实施方案,B选自与相邻的环稠合的无取代或任选被一个、两个或更多个X取代的以下结构,其中E和X具有上文所述的定义:
本发明还提供式(I)化合物的制备方法,包括以下步骤:
其中,A、B、D、E、X具有上文所述的定义;
(1)化合物a与化合物b反应得到化合物c;
(2)化合物c发生关环反应得到化合物d;
(3)化合物d与丙二腈反应得到式(I)化合物。
根据本发明的实施方案,步骤(1)中,所述反应可以在碱存在下进行,所述碱可以为有机金属试剂,所述有机金属试剂可以为甲基锂、丁基锂或二异丙基氨基锂中的至少一种。
根据本发明的实施方案,步骤(2)中,所述反应可以在催化剂存在下进行,所述催化剂可以为钯催化剂,所述钯催化剂可以为醋酸钯、二氯化钯、四(三苯基磷)钯、二(三苯基磷)二氯化钯中的至少一种;
根据本发明的实施方案,步骤(2)中,所述反应可以在配体化合物存在下进行,所述配体化合物可以为三环己基膦四氟硼酸盐、三苯基膦-2-双环己基膦-2',4',6'-三异丙基联苯、2-双环己基膦-2',6'-二甲氧基联苯中的至少一种;
根据本发明的实施方案,步骤(2)中,所述反应可以在碱存在下进行,所述碱可以为无机碱,所述无机碱可以为碳酸钾、碳酸钠或碳酸铯中的至少一种。
根据本发明的实施方案,步骤(3)中,所述反应可以在碱存在下进行,所述碱可以为有机碱,所述有机碱可以为吡啶、N,N-二甲氨基吡啶、三乙胺、二异丙基乙二胺中的至少一种。
根据本发明的实施方案,步骤(3)中,所述反应可以在催化剂存在下进行,所述催化剂可以为路易斯酸,所述路易斯酸可以为四氯化钛、氯化铝、氯化锌、三氟化硼中的至少一种。
本发明还提供式(I)所示化合物作为有机光伏受体的应用,例如在制备有机光伏器件中的应用。
本发明还提供一种有机光伏器件,所述光伏器件中包括本发明式(I)化合物制备的光敏层。
有益效果
本发明采用全稠环结构设计并制备了一系列小分子光伏受体,该结构中无环外双键的存在,避免了亲核试剂参与的加成反应的发生,同时有效提高了受体分子的光氧化稳定性以及热稳定性。本发明的制备方法极大减少了全稠环体系小分子受体的制备步骤,提高了制备效率。
附图说明
图1为实施例1制备的ITYM在氮气环境下热重分析曲线。
图2为实施例2制备的ITYM薄膜的循环伏安测试(乙腈溶液,100mV/s扫描速度,二茂铁校准)。
图3为实施例2制备的ITYM的溶液和薄膜的紫外可见吸收光谱。
图4为实施例3中ITYM的器件电压电流关系曲线。
图5为实施例3中ITYM的薄膜外量子效率曲线。
图6为实施例5中ITYM与其它小分子受体光照稳定性对比图。
图7为实施例6中ITYM与其它小分子受体对于亲核试剂稳定性对比图。
术语和定义
术语“C1-40烷基”应理解为表示具有1~20个碳原子的直链或支链饱和一价烃基。例如,“C1-10烷基”表示具有1、2、3、4、5、6、7、8、9或10个碳原子的直链和支链烷基,“C1-8烷基”表示具有1、2、3、4、5、6、7或8个碳原子的直链和支链烷基。所述烷基是例如甲基、乙基、丙基、丁基、戊基、己基、异丙基、异丁基、仲丁基、叔丁基、异戊基、2-甲基丁基、1-甲基丁基、1-乙基丙基、1,2-二甲基丙基、新戊基、1,1-二甲基丙基、4-甲基戊基、3-甲基戊基、2-甲基戊基、1-甲基戊基、2-乙基丁基、1-乙基丁基、3,3-二甲基丁基、2,2-二甲基丁基、1,1-二甲基丁基、2,3-二甲基丁基、1,3-二甲基丁基或1,2-二甲基丁基等或它们的异构体。
术语“C6-14芳基”应理解为优选表示具有6、7、8、9、10、11、12、13或14个碳原子的一价芳香性或部分芳香性的单环、双环或三环烃环(“C6-14芳基”),特别是具有6个碳原子的环(“C6芳基”),例如苯基;或联苯基,或者是具有9个碳原子的环(“C9芳基”),例如茚满基或茚基,或者是具有10个碳原子的环(“C10芳基”),例如四氢化萘基、二氢萘基或萘基,或者是具有13个碳原子的环(“C13芳基”),例如芴基,或者是具有14个碳原子的环(“C14芳基”),例如蒽基。当所述C6-20芳基被取代时,其可以为单取代或者多取代。并且,对其取代位点没有限制,例如可以为邻位、对位或间位取代。
术语“C5-14烯烃环”应理解为表示含有至少一个碳碳双键的单环或双环烃环,其具有5~14个碳原子。术语“C5-14烯烃环”应理解为表示含有碳碳双键的单环或双环烃环,其具有3、4、5、6、7、8、9、10、11、12、13或14个碳原子。所述C5-14烯烃环可以是单环烃基,如环戊烯环、环戊二烯环、环己烯环、环庚烯环、环辛烯环、环壬烯环或环癸烯环。
术语“5-14元杂环”意指包含1-5个独立选自N、O和S的杂原子的总成环原子数为3-14(如原子数为3、4、5、6、7、8、9、10等)的非芳族环状基团,优选“5-10元杂环”。术语“5-10元杂环”意指包含1-5个,优选1-3个选自N、O和S的杂原子的单环、双环烃环或桥环烷烃。所述杂环可以通过所述碳原子中的任一个或氮原子(如果存在的话)与分子的其余部分连接或者与相邻的环稠合。特别地,所述杂环可以包括但不限于:5元环,如四氢呋喃环、二氧杂环戊烯环、吡咯环、咪唑环、吡唑环、吡咯啉环;或6元环,如四氢吡喃环、哌啶环、吗啉环、二噻烷环、硫代吗啉环、哌嗪环或三噻烷环。
术语“C6-14芳环”应理解为优选表示具有6、7、8、9、10、11、12、13或14个碳原子的与相邻环稠和的芳香性或部分芳香性的单环、双环或三环烃环(“C6-14芳环”),特别是具有6个碳原子的环(“C6芳环”),例如苯环;或联苯环,或者是具有9个碳原子的环(“C9芳环”),例如茚满环或茚环,或者是具有10个碳原子的环(“C10芳环”),例如四氢化萘环、二氢萘环或萘环,或者是具有13个碳原子的环(“C13芳环”),例如芴环,或者是具有14个碳原子的环(“C14芳环”),例如蒽环。当所述C6-14芳环被取代时,其可以为单取代或者多取代。并且,对其取代位点没有限制,例如可以为邻位、对位或间位取代。
术语“5-14元杂芳环”应理解为具有5、6、7、8、9、10、11、12、13或14个环原子—特别是5或6或9或10个碳原子—且其包含1-5个—优选1-3个—独立选自N、O和S的杂原子的与相邻环稠和的单环、双环或三环芳族环基团,并且,另外在每一种情况下可为苯并稠合的。特别地,杂芳环选自噻吩环、呋喃环、吡咯环、噁唑环、噻唑环、咪唑环、吡唑环、异噁唑环、异噻唑环、噁二唑环、三唑环、噻二唑环等以及它们的苯并衍生物,例如苯并呋喃环、苯并噻吩环、苯并噁唑环、苯并异噁唑环、苯并咪唑环、苯并三唑环、吲唑环、吲哚环、异吲哚环等;或吡啶环、哒嗪环、嘧啶环、吡嗪环、三嗪环等,以及它们的苯并衍生物,例如喹啉环、喹唑啉环、异喹啉环等;或吖辛因环、吲嗪环、嘌呤环等以及它们的苯并衍生物;或噌啉环、酞嗪环、喹唑啉环、喹喔啉环、萘啶环、蝶啶环、咔唑环、吖啶环、吩嗪环、吩噻嗪环、吩噁嗪环等。
具体实施方式
下文将结合具体实施例对本发明的技术方案做更进一步的详细说明。应当理解,下列实施例仅为示例性地说明和解释本发明,而不应被解释为对本发明保护范围的限制。凡基于本发明上述内容所实现的技术均涵盖在本发明旨在保护的范围内。
除非另有说明,以下实施例中使用的原料和试剂均为市售商品,或者可以通过已知方法制备。
实施例1
中间体2:将1(500mg,0.83mmol)溶于20ml干燥四氢呋喃,冷却到-78℃后加入丁基锂的己烷溶液(1.6M,2.07mmol)。1小时后加入2-溴-N,N-二甲基苯甲酰胺,溶液恢复到室温后继续搅拌1h。加水淬灭反应,乙酸乙酯萃取,合并有机相后使用无水硫酸钠干燥,除去溶剂后使用柱层析法分离(石油醚/二氯甲烷=1/1),得到黄色固体2(563mg,收率70%)。1HNMR(400MHz,CDCl3):δ7.69(d,J=7.3Hz,2H),7.54–7.37(m,8H),7.28(s,2H),2.03–1.81(m,8H),1.16–1.02(m,24H),0.90–0.68(m,20H)。MALDI-TOF-MS(m/z):C54H66O2S2计算值:966.27[M+];实验值:966.27[M+]。
中间体3:在氮气保护下将醋酸钯(13mg,0.058mmol),三环己基膦四氟硼酸盐(85mg,0.23mmol),碳酸钾(320mg,2.32mmol)加入到2(563mg,0.58mmol)的DMF溶液中(10ml),回流过夜。将溶液倒入水中,二氯甲烷萃取后合并有机相,无水硫酸钠干燥,除去溶剂后柱层析法分离(石油醚/二氯甲烷=1/1)得到橙色固体3(313mg,收率67%)。1H NMR(400MHz,CDCl2CDCl2):δ7.47(d,J=7.2Hz,2H),7.42-7.34(m,4H),7.28-7.21(m,4H),2.24-2.07(m,8H),1.13–0.52(m,44H)。MALDI-TOF-MS(m/z):C54H62O2S2计算值:806.42[M+],实验值:806.41[M+]。
目标产物4(ITYM):将3(313mg,0.38mmol)和丙二腈(127mg,1.9mmol)溶于10ml氯苯,搅拌下加入0.5ml吡啶和0.5ml四氯化钛,50℃下搅拌10分钟。加水淬灭后除去溶剂,柱层析法分离(氯仿)得到灰黑色固体ITYM(292mg,收率89%)。1H NMR(400MHz,CDCl2CDCl2):δ8.14(d,J=7.6Hz,2H),7.48(s,2H),7.45–7.37(m,4H),7.26(t,J=7.4Hz,2H),2.32–2.06(m,8H),1.13–0.59(m,44H)。MALDI-TOF-MS(m/z):C60H62N4S2计算值:902.44[M+],实验值:902.44[M+]。
实施例2 ITYM薄膜制备方法及性能测试
将ITYM的氯仿溶液(3mg/ml)滴加至测试电极之上,待溶剂挥发形成均匀薄膜之后进行循环伏安测试(见图2,乙腈溶液,100mV/s扫描速度,二茂铁校准)。
将ITYM的氯仿溶液(3mg/ml)旋涂于石英片上(3000转/秒),待溶剂挥发即可进行紫外可见吸收测试(见图3)。
实施例3器件制备及性能测试
器件结构为ITO/PEDOT:PSS/PM6:ITYM/PDINN/Ag,先将图案化的ITO玻璃基材在洗涤剂、去离子水、丙酮和异丙醇中连续超声波处理预清洁,并通过高压空气流干燥衬底,然后进一步在臭氧室中暴露处理30分钟以除去所有残余有机物。首先在ITO玻璃基材上旋涂一层PEDOT:PSS薄膜(4000转/秒),然后在150℃热板上退火15分钟,随后转移进充满氮气的手套箱中。随后将PM6与ITYM(给受体比例1/1.2)的混合氯仿溶液(总浓度15.4mg/ml)(含0.25%1-氯萘)旋涂至PEDOT:PSS薄膜之上形成光敏层,100度进行热退火后,将PDINN的甲醇溶液旋涂至光敏层之上(3000转/秒),在高真空下,以热蒸发方式通过阴影掩模将Ag层(100nm)沉积至PDINN层之上,器件面积为0.04cm2。利用上述器件测试了ITYM的器件电压电流关系曲线(见图4)和外量子效率曲线(见图5),器件参数如下:
开路电压[V] | 短路电流[mA/cm<sup>2</sup>] | 填充因子[%] | 效率[%] |
0.91 | 14.65 | 71.73 | 9.51 |
实施例4 ITYM热稳定性测试及其与IDIC、ITIC、IT-4F的对比
分别取2mg ITYM、IDIC、ITIC、IT-4F放入铂制托盘中,置于热重分析仪之中进行测试(升温速率10℃/s),当重量损失比例达到5%时读取分解温度如下:ITYM:324℃,IDIC:282℃,ITIC:314℃,IT-4F:316℃。结果表明全稠环分子ITYM的热稳定性相较于常见小分子受体有所提高。
实施例5 ITYM光照稳定性测试及其与IDIC、ITIC、IT-4F的对比
将ITYM、IDIC、ITIC、IT-4F四种化合物分别配制成浓度为10-5mol/L的溶液(溶剂为四氢呋喃),各取2.5ml加入四个气密四通比色皿中,盖好后测试其吸光度,然后将溶液置于模拟太阳光(AM1.5G)下进行照射,每隔10分钟进行一次吸光度测试(ITIC间隔3分钟,IT-4F间隔2分钟)。依次取四种溶液最大吸收波长处的吸光度数值并进行归一化处理对比发现:ITIC溶液在照射12分钟后吸光度降低至0,IT-4F溶液在照射8分钟后吸光度降低至0,IDIC溶液在照射60分钟后吸光度降低至初始值的45%,而ITYM溶液在照射60分钟后仍然保持了70%的初始吸光度(见图6)。结果表明四种分子中ITYM在光照条件下具有更高的稳定性。
实施例6 ITYM对于亲核试剂稳定性测试及其与IDIC、ITIC、IT-4F的对比
将ITYM、IDIC、ITIC、IT-4F四种化合物分别配制成浓度为10-5mol/L的溶液(溶剂为四氢呋喃/水,体积比为v/v=96/4),各取2.5ml加入四个气密比色皿中,盖好后测试其吸光度,然后加入乙醇胺(乙醇胺浓度为10-3mol/L),立即再次进行吸光度测试,之后依次于加入乙醇胺10分钟、30分钟、1小时、3小时、5小时、8小时、12小时后进行吸光度测试,并取最大吸收波长处的吸光度数值,经归一化处理后对比发现:ITIC与IT-4F在加入乙醇胺12小时后吸光度基本衰减至0,IDIC衰减至初始值的20%,而ITYM在12小时之后依然保持了95%的吸光度(见图7)。结果表明四种分子中ITYM对于亲核试剂的稳定性更高。
以上,对本发明的实施方式进行了说明。但是,本发明不限定于上述实施方式。凡在本发明的精神和原则之内,所做的任何修改、等同替换、改进等,均应包含在本发明的保护范围之内。
Claims (9)
2.根据权利要求1所述的化合物,其特征在于,A选自无取代或任选被一个、两个或更多个R取代的苯环或稠环,所述稠环由两个或更多个环戊二烯、噻吩、吡咯、吡喃、吡嗪、噻二唑或苯稠合形成;每个R相同或不同,彼此独立地选自丁基、戊基、己基、庚基、辛基、壬基、癸基、2-乙基己基、2-己基癸基、2-辛基十二烷基、2-癸基十四烷基、4-己基苯基。
7.权利要求1至5任一项所述化合物作为有机光伏受体的应用。
8.权利要求1至5任一项所述化合物在制备有机光伏器件中的应用。
9.一种有机光伏器件,所述光伏器件中包括权利要求1至5任一项所述化合物制备的光敏层。
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