CN104428914A - 包含基于酰亚胺的共轭骨架化合物作为光活性材料的体异质结型有机太阳能电池 - Google Patents
包含基于酰亚胺的共轭骨架化合物作为光活性材料的体异质结型有机太阳能电池 Download PDFInfo
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Abstract
本发明涉及太阳能电池,其至少包含衬底(10)、阴极(11)、空穴导电层(12)、施主材料与受主材料的共混物的体异质结光活性层(13)、电子导电层(14)和阳极(15),其中该共混物包含至少一种含共轭骨架体系的光活性材料,该共轭骨架体系具有:i)通式R2-酰亚胺-Ar-L-Ar-酰亚胺-R3,其中Ar-L-Ar是共轭的发色团,酰亚胺是酰亚胺-OCNCO-,R2和R3是键合至各个酰亚胺的N原子并且与各个酰亚胺形成共轭键的有机基团;或者ii)重复单元(R4-酰亚胺-Ar-L-Ar-酰亚胺)n,其中Ar-L-Ar是共轭的发色团,酰亚胺是酰亚胺-OCNCO-,R4是键合至各个酰亚胺的N原子并与各个酰亚胺形成共轭键的有机基团,并且n是重复单元的数目。
Description
本发明涉及体异质结(BHJ)型有机太阳能电池。通常,这种太阳能电池至少包括衬底、阴极、空穴导电层、施主材料与受主材料的共混物的体异质结光活性层、电子导电层和阳极。
由于易加工、轻质和潜在低成本的前景,由有机光活性材料构成的光伏器件—下文称为有机太阳能电池—已获得了许多科学关注。许多这些有机太阳能电池包含基于共轭聚合物的光活性材料作为电子施主和空穴传导体。因为聚合物加工得到很好发展,预期已知的卷到卷(roll-to-roll)加工技术,如刮刀涂布、喷涂、印刷和辊涂可应用于制备有机太阳能电池,特别是在柔性支撑物上的大面积、廉价的太阳能电池,这将会打开巨大数目的可能应用。由于发现了所谓体异质结概念,对有机太阳能电池的兴趣已进一步提高,所述体异质结概念特别关注于优化在施主有机相和受主有机相的共混物中施主有机相和受主有机相之间的界面,在所述界面处激子离解成电子和空穴并由此引起电荷流动。
传统上,使用共轭化合物诸如MDMO-PPV、P3HT等作为施主相,以便吸收光以及产生激子并将其转移至与受主相的界面,激子离解发生在该界面处。对于受主相,C60、PCBM、CN-PPV等经常被用作示例性的材料。
这些已知光活性材料的一个缺点(无论施主或受主)涉及它们复杂的合成工艺,包括提纯以便除去在合成中使用的金属催化剂,从而获得电子级材料。在这些材料的制备期间以及在由其所得的太阳能电池的生产期间都需要严格的条件。此外,这些材料对氧气和水蒸气敏感。该敏感涉及劣化和形貌变化的风险,尤其在高于室温的温度下,并且因此光活性材料有可能发生降低的效率和有限的寿命。
本发明的一个目的是提供体异质结型有机太阳能电池,其中光活性材料,无论是依赖于各自电子亲和性的施主或受主,不具有或者至少在较小程度上具有已知材料的上述缺点。
此外,本发明的一个目的是提供如包含光活性材料的这种太阳能电池,其可以使用简单的方法制得。
本发明的另一个目的是提供具有长的使用寿命的体异质结型有机太阳能电池,更特别是包含在整个服役期间显示出改善的稳定性和/或固定的形貌的光活性材料的这种电池。
根据本发明,通过如下的太阳能电池实现上述目的中的一个或多个:该太阳能电池至少包括衬底、阴极、空穴导电层、施主材料和受主材料的共混物的体异质结光活性层、电子导电层和阳极,其中该共混物包含至少一种含有共轭骨架体系的光活性材料,该共轭骨架体系具有:
i)通式R2-酰亚胺-Ar-L-Ar-酰亚胺-R3,其中
Ar-L-Ar是共轭的发色团;
酰亚胺是酰亚胺-OCNCO-;
R2和R3是是键合至各个酰亚胺的N原子并与各个酰亚胺形成共轭键的有机基团;或者
ii)具有重复单元(R4-酰亚胺-Ar-L-Ar-酰亚胺)n,其中
Ar-L-Ar是共轭的发色团;
酰亚胺是酰亚胺-OCNCO-;
R4是键合至各个酰亚胺的N原子并与各个酰亚胺形成共轭键的有机基团,
并且n是重复单元的数目。
在根据本发明的具有共同构造的太阳能电池中,在体异质结光活性层中含有的共混物包含基于酰亚胺的共轭骨架化合物作为施主或受主中的至少一种。该化合物要么是具有如i)中所定义的通式R2-酰亚胺-Ar-L-Ar-酰亚胺-R3的小(“单”)分子要么是具有重复单元(R4-酰亚胺-Ar-L-Ar-酰亚胺)n的聚合物化合物。在所述化合物中,共轭的发色团Ar-L-Ar和共轭酰亚胺基以及各自与各个酰亚胺基的N原子形成共轭键的有机基团R2、R3和R4是该化合物的主链的共轭键体系的一部分。由此,R2、R3和R4至少包括在连接至酰亚胺基的N原子的第一碳原子和邻近碳原子之间的双键。优选地该共轭键体系延伸遍及R2、R3和/或R4烃基。根据光活性材料的配应物(counterpart)和电子亲和性,所述光活性材料在本发明的太阳能电池中充当施主或受主。具有基于二酰亚胺或聚酰亚胺的共轭骨架的这种光活性材料(在其共轭骨架之中还包含共轭的发色团)是耐热和耐化学性的,并且与现有技术材料相比显示出对氧气和湿气的改善的耐受性。通常,在根据本发明的太阳能电池中使用的光活性材料具有固定的形貌(即使在高于环境温度的温度)和改善的使用寿命,因为基于酰亚胺化和聚合(若有的话)的光活性材料将不经历另外的化学反应或再定位(reorientation)。
在此指出,基于酰亚胺的化合物本身是已知的。例如,JP04306234公开了具有结构单元IV的聚酰亚胺共聚物,其中R是双官能有机基团(优选地由其制备中使用的长链芳香二胺衍生)并且m是1至3。
这种共聚物包含含有呋喃结构部分(moiety)、至少两个酰亚胺基-OCNCO-、以及为有机基团的R的共轭骨架。据称这种聚酰亚胺共聚物具有优异的耐热性、高的弹性模量、低的热膨胀、低的介电常数和低的水蒸气吸收。
从WO 2011/158211A1知晓了一种具有式(F)的有机半导体材料,其特别具有用于薄膜晶体管的n型特性,
其中,A表示包含至少一个芳环的环状共轭骨架结构并且R1和R2各自独立地是取代的或未取代的烷基。由于R1和R2的这种特性,这些基团不形成贯穿主链的共轭键体系。据称氟取代的烷基作为式(F)中的R1和R2允许防止杂质(诸如水、氧和空气)渗入有机半导体薄膜,并且由此显示出稳定的n型半导体特性。
JP 2010254608A公开了一种用于有机薄膜太阳能电池的光电转换材料。这种已知的材料包含化合物:
其中,L是二价或三价基团,Rg是取代或未取代的苯或萘环,X是O或NR1,其中R1可以特别是取代或未取代的C1-20烯基。使用该材料作为用于替代典型双层太阳能电池设计中的LiF的电荷传输化合物。
本发明的概念允许选择合适的发色团Ar-L-Ar,特别是其L结构部分,这提供了调整至期望性能的灵活性,例如在近紫外和可见光谱中的光吸收,尤其是后者。以这种方式,分子可以被设计成施主以及受主,因为发色团是主要造成吸收的化合物的一部分。
连接至酰亚胺基的氮原子的基团R2、R3和R4延伸共轭体系并有助于光的吸收,以及被认为是用于使光活性材料溶解在有机太阳能电池生产中典型使用的溶剂中的增溶基。优选地,基团R1、R2和R2选自取代或未取代的烯基、取代或未取代的不饱和环状烃基。
在本发明中,所述至少一个共轭的发色团的L结构部分不直接连接于共轭骨架中的酰亚胺基,但是中间偶联基团(coupling group)Ar位于各个酰亚胺基和L结构部分之间。Ar是共轭有机基团。芴和咔唑是其实例。更优选地Ar是芳基,例如苯基。该共轭有机基团可以是取代的。有利地,L结构部分包含含有选自Si、S、N和O的至少一个杂原子的共轭有机基团,有利地为单环或多环基团。优选地,L结构部分包含含有选自Si、S、N和O的1-3个杂原子的至少一个5元有机环基团。在多环L结构部分中,例如所述5元有机环基团可以稠合到具有共轭键的其它5元或6元有机基团。
在根据本发明的太阳能电池的优选实施方案中,所定义的光活性材料起到施主的作用。已知的受主材料可以用作相对物。优选地,共混物包含根据本发明的不同的光活性材料作为施主和受主两者。
光活性材料在共轭骨架中包含至少两个酰亚胺基。由于合成的原因,由酰亚胺-Ar构成的部分优选地包含邻苯二甲酰亚胺基。具有基于酰亚胺的共轭骨架的光活性材料可以是在其共轭体系中包含至少两个酰亚胺结构部分的小分子。
在小分子的实施方案中,光活性材料包含具有通式R2-酰亚胺-Ar-L-Ar-酰亚胺-R3的化合物,其中,
Ar-L-Ar是如上说明的包括L结构部分和共轭有机基团Ar的上述优选项的共轭发色团,
酰亚胺是酰亚胺-OCNCO-;并且
R2和R3是连接至酰亚胺的N原子并与各个酰亚胺基形成共轭键的有机基团。典型地,R2和R3相同。
在根据本发明的太阳能电池中使用的光活性材料的典型实例包括:
5,5’-(1,3,4-噁二唑-2,5-二基)双(2-(4-(二苯基氨基)苯基)异吲哚啉-1,3-二酮)
5,5’-(噻吩-2,5-二基)双(2-(4-二苯基氨基)苯基)异吲哚啉-1,3-二酮)
5,5’-(1,3,4-噻二唑-2,5-二基)双(2-(4-(二苯基氨基)苯基)异吲哚啉-1,3-二酮)
5,5’-(苯并[c][1,2,5]噻二唑-4,7-二基)双(2-(4-(二苯基氨基)苯基)异吲哚啉-1,3-二酮)
5,5’-(噻吩并[3,2-b]噻吩-2,5-二基)双(2-(4-(二苯基氨基)苯基)异吲哚啉-1,3-二酮)
5,5’-(2,3-二甲基噻吩并[3,4-b]吡嗪-5,7-二基)双(2-(4-(二苯基氨基)苯基)异吲哚啉-1,3-二酮)
在根据本发明的太阳能电池中使用的光活性材料的聚合物实施方案中,该光活性材料包含具有重复单元(R4-酰亚胺-Ar-L-Ar-酰亚胺)n的聚合物,
其中,
Ar-L-Ar是共轭的发色团,
酰亚胺是酰亚胺-OCNCO-;
R4是键合至酰亚胺的N原子并与各个酰亚胺形成共轭键的有机基团;并且
n是重复单元的数目。
在共轭的发色团Ar-L-Ar中的L结构部分和基团Ar的有利并优选的实施方案如上所定义。重复单元的数目未具体限定,通常它会在约200至约例如6000的范围内。
包含至少一个杂原子的L结构部分的实例包括下面左栏中所示的包含一个或两个含杂原子的5元或6元环的化合物。第二列示出了在本发明中使用的聚合物化合物中的基团R4的实例。第三列至第五列示出了本发明的小分子中的基团R2和R3的典型实例。
关于有机基团R2、R3和R4,它们可以是与各个酰亚胺基形成共轭键的任何基团。实例特别包括如上所说明的芳香胺,以及在右手侧的芳香族化合物。
在根据本发明的太阳能电池中使用的光活性材料能够容易地制得,例如使用包含(芳族)羧酸二酐与胺R2-NH2(优选芳香胺)的酰亚胺化反应的方法,由此在如此形成的酰亚胺结构部分处获得共轭键,其中R2如上定义并且参与共轭键体系。
如在本发明中使用的聚合物光活性材料的制造中,允许二酐与二胺反应。
通过附图和实施例进一步说明本发明。
在附图中,
图1示出了酰亚胺结构部分。
图2和3示出了合成路线,其中图3是关于制备在根据本发明的太阳能电池中使用的光活性层的酰亚胺骨架结构的说明;
图4示出了小分子(低聚物)和聚合物酰亚胺的实例;
图5示出了根据本发明的合成实例;和
图6示出了根据本发明的太阳能电池的实施方案。
图7示出了实施例2的小分子化合物以及其与PCBM结合的紫外-可见(UV-Vis)光谱。
图8示出了实施例2的小分子化合物的循环伏安法的结果。
图9示出了几种二酰亚胺化合物的吸收光谱。
图1示出了酰亚胺结构部分,其中表示基团R2、R3和R4的R基团连接至酰亚胺的N原子。
在图2中,说明了从芳香单胺和芳香酐(后者包含5元杂环)开始的缩合反应的常规路线。特别地,允许1,3-二氢-2-苯并呋喃-1,3-二酮与苯胺反应由此产生芳族酰亚胺产物2-苯基-2,3-二氢-1H-异吲哚啉-1,3-二酮。
图3示出了从二胺和二酐开始制备根据本发明的太阳能电池中使用的光活性材料的常规路线。特别地,允许包含共轭L结构部分的芳族(表示基团Ar)二酐与芳族二胺反应,从而形成(聚)酰胺酸中间产物,可以通过热或化学酰亚胺化直接转变成聚酰亚胺骨架结构。
图4示出了小分子和聚合物酰亚胺各自的酰亚胺骨架的2个实例。
图5示出了具体的实例,其中1,3-二氧-1,3-二氢-2-苯并呋喃-5-羧酸在硫酸(66%SO3)的存在下与乙二胺反应产生二酐,这允许使用回流在冰醋酸中与苯胺-二苯基胺反应,由此获得5,5’-(1,3,4-噁二唑-2,5-二基)双(2-(4-(二苯基氨基)苯基)异吲哚啉-1,3-二酮)。
图6说明了体异质结有机太阳能电池,其中衬底以附图标记10表示并且带有电极层11,所述衬底是例如来自玻璃或塑料的透明衬底或者由诸如钢或铝制成的(电隔离的)薄金属箔。在该电极层的上方设置电荷传输层12。活性层13包含根据本发明的光活性材料,例如在共混物中的施主及其相对物(受主如芴及其衍生物)。在其上方设置进一步的电荷传输层14以及透明电极层15。
实施例2说明了在本发明中使用的化合物的制备方法。
实施例1。5,5’-(1,3,4-噁二唑-2,5-二基)双(异苯并呋喃-1,3-二酮)的合成。
向配备有搅拌棒、冷凝器和N2入口的1L三颈烧瓶中装入77g的1,3-二氧-1,3-二氢异苯并呋喃-5-羧酸(401mmol)和200mL的发烟硫酸(65%游离SO3)。将所得到的悬浮液加热至75℃并搅拌直至所有的1,3-二氧-1,3-二氢异苯并呋喃-5-羧酸溶解。分次加入硫酸肼盐(23.7g,182mmol)并将反应混合物加热至90℃并在该温度下搅拌4小时。
将反应混合物倒在碎冰上并滤出白色沉淀物。通过在水中搅拌直至pH为中性来洗涤粘性白色固体。通过与300mL甲苯的共沸蒸馏以及进一步在真空炉中在50℃下干燥一整夜以除去残留水从而产生61g白色固体形式的粗制品。
将30g的粗制品在200mL醋酸酐中在90℃下搅拌3小时。滤出固体并用己烷洗涤(3×100mL)并在真空炉中在50℃下干燥一整夜。产生21g白色固体形式的标题化合物(58mmol,29%)。
实施例2。5,5’-(1,3,4-噁二唑-2,5-二基)双(2-(4-(二苯基胺基)苯基)异吲哚啉-1,3-二酮)的合成。
向配备有搅拌棒、冷凝器和N2入口的250mL三颈烧瓶中装入10g的5,5’-(1,3,4-噁二唑-2,5-二基)双(异苯并呋喃-1,3-二酮)(27.6mmol)、15.8g的N1,N1-二苯基苯-1,4-二胺(2.2eq.)和100mL的冰醋酸。将所得到的悬浮液加热至回流温度并在该温度下搅拌8小时。
将反应混合物倒在碎冰上并滤出橙色沉淀物。用水(2×100mL)和己烷(2×100mL)洗涤该固体。将滤液溶解在热氯仿中并过滤。使溶液冷却至室温并滤出沉淀的橙色固体。使该固体在真空炉中在60℃下干燥一整夜。产生20.8g橙色固体形式的标题化合物(24.6mmol,89%)。
%).1H NMR(300MHz,CDCl3)δppm 8.90(m,2H),8.83(m,2H),8.35(m,2H),7.48(m,12H),7.36(m,12H),7.27(m,4H);13C NMR(100MHz,CDCl3)δppm 166.28,166.18,163.91,147.93,147.22,134.28,132.91,132.84,129.41,128.90,127.13,125.01,124.63,124.52,123.58,122.77和121.98。
实施例3。制造太阳能电池
将实施例2的小分子和芴衍生物以1:1的重量比溶解在如下表1所示的各自溶剂中并且将溶液在所示的60℃或100℃下搅拌。在空气中在洁净的玻璃衬底上旋涂光活性层,该玻璃衬底预图案化有铟锡氧化物和60nm厚的聚(3,4-乙烯二氧噻吩)/聚苯乙烯磺酸的膜。通过在1×10-6mbar下热蒸发LiF(1nm)/Al(100nm)的阴极来完成该器件。在N2受控气氛中在黑暗中以及在Steuernagel SolarCons tant 1200金属卤化物灯照射下来进行电测量,其中使用硅参比池和校正光谱失配来将该金属卤化物灯设置为1个太阳强度。
表1
溶剂 | T(℃) | PCBM | JSC | VOC | FF | Eff |
ODCB | 60 | [60] | 0.63 | 1.03 | 0.27 | 0.17 |
ODCB | 60 | [70] | 0.64 | 0.67 | 0.26 | 0.11 |
CB | 100 | [60] | 0.13 | 1.07 | 0.26 | 0.04 |
CB | 100 | [70] | 0.59 | 0.57 | 0.26 | 0.09 |
CHCl3 | 60 | [60] | 0.10 | 1.05 | 0.25 | 0.03 |
CHCl3 | 60 | [70] | 0.30 | 0.89 | 0.25 | 0.07 |
图7示出了实施例2的标题化合物(下部线)和以1∶1比例的标题化合物:PCBM(上部线)的紫外-可见光谱,两者均使在从CHCl3旋涂的膜中记录的。
图8是示出了对实施例2的标题化合物进行的循环伏安法的结果的曲线图。发现了相对于Fc/Fc+的0.44V的氧化电势。
实施例4
进行5,5’-(1,3,4-噁二唑-2,5-二基)双(2-(4-(二苯基氨基)苯基)异吲哚啉-1,3-二酮)和5,5’-(噻吩-2,5-二基)双(2-(4-(二苯基氨基)苯基)异吲哚啉-1,3-二酮)的紫外-可见光吸收,由此L结构部分是1,3,4-噁二唑或噻吩。为了对比,也对TPA-PMDA-TPA和TPA-sBPDA-TPA进行了检测,其中TPA表示三苯基胺并且PMDA代表均苯四甲酸二酐,SBPDA是联苯基-四羧酸二酐。图9示出了在CHCl3中于5mg/L浓度下的结果。观察到从TPA-PMDA-TPA经由TPA-sBPA-TPA和TPA-噁二唑-TPA至TPA-噻吩-TPA的朝向可见光谱波长的延伸。
该图示出了通过改变L结构部分的朝向可见光谱的光吸收偏移,TPA-噻吩-TPA显现出这些所检测化合物中的最好结果。
实施例5
与实施例3相似,从实施例4的光活性材料制造太阳能电池(从氯仿旋涂,60℃,30mg/mL总浓度,小分子光活性材料:[60]PCBM比率=1∶3)。表2给出了结果。*表示在120℃下退火2分钟的器件,并且太阳能电池的面积分别是a=0.09cm2或b=0.16cm2。
表2
L部分 | JSC | VOC | FF | MPP | |
a | 0.121 | 0.58 | 0.29 | 0.0204 | |
a* | 0.0748 | 0.48 | 0.23 | 0.00822 | |
b | 0.177 | 0.59 | 0.29 | 0.0307 | |
噁二唑 | a | 0.0862 | 0.48 | 0.3 | 0.0123 |
a* | 0.0506 | 0.39 | 0.24 | 0.00482 | |
b | 0.087 | 0.39 | 0.3 | 0.0128 | |
PMDA | a | 0.0436 | 0.66 | 0.27 | 0.00769 |
a* | 0.0184 | 0.56 | 0.29 | 0.0019 | |
b | 0.0413 | 0.67 | 0.27 | 0.00745 | |
sBPDA | a | 0.0715 | 0.68 | 0.26 | 0.0124 |
a* | 0.045 | 0.6 | 0.2 | 0.00536 | |
b | 0.0673 | 0.69 | 0.25 | 0.0118 | |
类似地,从60℃的ODCB旋涂器件,面积是0.09cm2。结果示于下表3中。
表3
发色团L | JSC | VOC | FF | MPP | |
噻吩 | 0.689 | 0.91 | 0.26 | 0.165 | |
退火的 | 0.873 | 0.75 | 0.34 | 0.22 | |
噁二唑 | 0.317 | 0.65 | 0.26 | 0.054 | |
退火的 | 0.508 | 0.69 | 0.29 | 0.101 | |
sBPDA | 0.68 | 0.26 | 0.0715 | 0.0124 | |
退火的 | 0.6 | 0.2 | 0.045 | 0.00536 | |
这些结果显示从ODCB制成的电池的性能好于从CHCl3制成的那些电池并且可使用退火来改善性能。最好的性能是对于作为L结构部分的噻吩的0.22%。
Claims (9)
1.太阳能电池,其至少包含衬底(10)、阴极(11)、空穴导电层(12)、施主材料与受主材料的共混物的体异质结光活性层(13)、电子导电层(14)和阳极(15),其中该共混物包含至少一种含共轭骨架体系的光活性材料,该共轭骨架体系具有:
i)通式R2-酰亚胺-Ar-L-Ar-酰亚胺-R3,其中
Ar-L-Ar是共轭的发色团;
酰亚胺是酰亚胺-OCNCO-;
R2和R3是键合至各个酰亚胺的N原子并与各个酰亚胺形成共轭键的有机基团;或者
ii)重复单元(R4-酰亚胺-Ar-L-Ar-酰亚胺)n,其中
Ar-L-Ar是共轭的发色团;
酰亚胺是酰亚胺-OCNCO-;
R4是键合至各个酰亚胺的N原子并与各个酰亚胺形成共轭键的有机基团;
并且n是重复单元的数目。
2.根据权利要求1的太阳能电池,其中,R2、R3、R4选自取代的或未取代的烯基、取代的或未取代的不饱和环状基团。
3.根据前述权利要求任一项的太阳能电池,其中,R2、R3、R4包含芳香族氨基。
4.根据前述权利要求任一项的太阳能电池,其中,所述酰亚胺是5元环状基团的一部分。
5.根据前述权利要求任一项的太阳能电池,其中,所述发色团Ar-L-Ar中的基团L包含含有选自Si、S、N和O中的至少一个杂原子的有机基团。
6.根据前述权利要求任一项的太阳能电池,其中,所述发色团Ar-L-Ar中的基团L包含至少一个5元有机环基团,该至少一个5元有机环基团包含1-3个选自Si、S、N和O的杂原子。
7.根据前述权利要求任一项的太阳能电池,其中,所述发色团Ar-L-Ar中的基团L选自如下:
8.根据前述权利要求任一项的太阳能电池,其中,Ar表示芳基。
9.根据前述权利要求任一项的太阳能电池,其中,所述酰亚胺-Ar包括邻苯二甲酰亚胺基团。
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PCT/EP2013/001599 WO2014000850A1 (en) | 2012-06-25 | 2013-05-31 | Organic solar cell of the bulk heterojunction type comprising an imide based conjugated backbone compound as photoactive material |
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CN104831400A (zh) * | 2015-05-22 | 2015-08-12 | 江苏宝德新材料有限公司 | 一种低粘度芳族聚噁二唑溶液及由其制得的纤维 |
CN109314184A (zh) * | 2016-03-15 | 2019-02-05 | 默克专利股份有限公司 | 有机半导体 |
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