以苯并三唑为主的多种含氮杂环构筑共轭聚合物及其光电性能研究
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摘要
共轭聚合物由于具有良好的环境和热稳定性,多样化的种类,可柔性加工性和有趣的光电特性,在有机半导体领域应用广泛。杂环化合物引入到共轭聚合物会产生特殊的电子结构变化和不同的光电性能,可作为聚合物发光二极管材料,聚合物场效应晶体管和聚合物太阳电池给体材料。在有机发光二极管中含杂环单元的聚合物作为发光活性层,可制备红绿蓝三色可见光和白光器件。杂环化合物作为缺电子单元与富电子单元共聚可得到多种窄带隙聚合物,与太阳光谱更加匹配,提高太阳光能利用率。
本论文是从研究苯并三唑杂环开始,首先合成4,7-二噻吩-2-十二烷基-2,1,3-苯并三唑单体,并与常见的给电子单元芴,咔唑和烷氧基苯通过Suzuki缩聚反应得到三个交替聚合物PF-DTBTA, PCz-DTBTA和PPh-DTBTA。当聚合物与受体PCBM的共混比为1:2时,对于聚合物PF-DTBTA、PCz-DTBTA和PPh-DTBTA作为给体并且Al作为阴极的器件来说,电池效率分别是0.9%,1.51%和1.16%。当用PFN/Al作双层阴极时,如果相对于Al作为阴极开路电压有损失就会被恢复弥补。对于苯并三唑类聚合物,当阴极是PFN和Al双层时,由于苯并三唑类给体聚合物和PFN层有N-N相互作用,短路电流和填充因子会有相应的提高;从而对于聚合物PF-DTBTA、PCz-DTBTA和PPh-DTBTA作为电子给体说,相应的电池效率可以提高到1.3%, 2.75%和1.39%。电池效率提高最多的是聚合物PCz-DTBTA作为给体的器件,增幅有80%,这暂时归因于是咔唑单元和PFN层有额外的氮-氮相互作用。这些结果对研究电池器件界面修饰来说是有用的。我们的结果也表明双层阴极是有提高太阳电池效率的潜力的。
第三章合成了一系列芴和二噻吩苯并三唑单元共聚的聚合物获得高效黄光,橙光和白光聚合物发光二极管。共聚物PF-DTBTA0.03?15是无规聚合物,而共聚物PF-DTBTA50是交替聚合物。八个能量转移型共聚物的薄膜具有高的光致发光外量子效率,在60?72%范围。共聚物PF-DTBTA1?15是黄光聚合物,外量子效率高达5.78%,而共聚物PF-DTBTA50是橙光聚合物,外量子效率约为3.3%。单元DTBTA含量高的交替聚合物PF-DTBTA50获得高的PL效率和外量子效率表明单元DTBTA是在固态PL和EL过程中受低浓度淬灭效应影响的高效发色团。由于从芴链段单元部分能量转移到单元DTBTA,单元DTBTA较低含量的共聚物PF-DTBTA0.03?0.1获得白光电致发光。在白光发光二极管中我们获得了流明效率高达11 cd/A的非掺杂单一白光聚合物。
第四章合成了二噻吩并苯单体,并与苯并三唑,二噻吩苯并三唑,喹喔啉,二噻吩喹喔啉和吡咯并吡咯二酮缺电子单元共聚得到五个交替聚合物PBDT-BTA, PBDT-DTBTA, PBDT-Q, PBDT-DTQ和PBDT-PhDPP。不同聚合物太阳电池器件的开路电压与聚合物的HOMO能级是相反关系。对聚合物PBDT-BTA和PBDT-DTBTA的化学结构进行比较,额外多出的噻吩单元能减少聚合物的有效共轭长度,以至于聚合物的HOMO能降低和相应的开路电压变大。噻吩桥的作用同样对聚合物PBDT-Q也是有效的。聚合物PBDT-PhDPP为给体的器件,使用不同阴极,发现双层阴极可以提高其开路电压,并且PFN/铝阴极提高最多。
第五章首次合成了两种基于烷氧基不同位置取代的喹喔啉的菲共聚物,作为聚合物给体材料应用在体异质结聚合物太阳电池。对比对位取代和间位取代,对位取代的聚合物可以拉低聚合物的HOMO能级和LUMO能级。尽管如此,聚合物器件开路电压却不是相同的结果,对位取代的反而高些。器件结果表明对位烷氧基取代苯的喹喔啉聚合物PPN-p-DTQ与PCBM共混比为1:2的器件开路电压比相同共混比例下的间位烷氧基取代苯的喹喔啉聚合物PPN-m-DTQ的较低一点,然而在共混比为1:4,器件开路电压的情况相反。
Conjugated polymers are widely utilized in organic semiconductor device due to their excellent environmental stability, thermal stability, diversity, processability and interesting optoelectronic properties. Incorporating heterocycles into conjugated polymers could induce the change of electronic properties of conjugated polymers, and different optoelectronic properties, which are candidates for polymer light-emitting diodes, polymer field-effect-transistor and polymer solar cells. Heterocycle-based copolymers as the active layer can emit red, green, blue and white light in OLED. Copolymers of heterocycle compounds as electron-poor unit and electron-rich unit as comonomer are widely used in BHJ PVCs to match the spectra of solar photons and effectively utilize it.
In the beginning, this dissertation is focusing on the optoelectronic properties of benzotriazole unit. In chapter 2, three BTA-based conjugated polymers PF-DTBTA, PCz-DTBTA, and PPh-DTBTA, with electron-donating segments of fluorene, carbazole, and dialkoxybenzene respectively, were successfully synthesized as new polymeric donors in BHJ PVCs. Using PFN/Al bilayer cathode could elevate Voc if Voc loss was encountered when using Al cathode. Using PFN/Al bilayer cathode could also improve Isc and FF for the three BTA-based copolymers, from which N-N interactions between the BTA-based polymers and the PFN were proposed. Consequently, PFN/Al bilayer cathode elevated PCE values. The most significant increasing of PCE with a calculated value of 80% was found for PCz-DTBTA as the donor, and this might be related to the additional N-N interactions between the carbazole segments and the PFN. The results would supply useful information to understand the contribution of an interfacial layer on the photovoltaic performances. Our results also suggest that the bilayer cathode would have great potential to elevate PCE of BHJ PVCs.
In chapter 3, a series of conjugated polymers PF-DTBTA derived from 2,7-fluorene and 4,7-dithienylbenzotriazole (DTBTA) were developed for high efficiency PLEDs with multi-colors of yellow, orange, and white lights. The PF-DTBTA0.03?15 are random copolymers while the PF-DTBTA50 is an alternating copolymer. PF-DTBTA1?15 showed yellow EL with EQEmax up to 5.78% while PF-DTBTA50 displayed orange EL with EQEmax of 3.3%. The highΦPL and EQEmax of PF-DTBTA50 with very high DTBTA content indicate that DTBTA is a high efficiency chromophore with very low concentration quenching effects in the solid state PL and EL processes. Introducing very low DTBTA contents in PF-DTBTA0.03?0.1 achieved white EL due to partial energy transfer from fluorene segments to the DTBTA units. WPLEDs with maximum luminous efficiency (LEmax) up to 11 cd/A could be realized from the non-doped single-polymer.
In chapter 4, five BDT-based conjugated polymers PBDT-BTA, PBDT-DTBTA, PBDT-Q, PBDT-DTQ, and PBDT-PhDPP, with electron-accepting segments of benzotriazole, 4,7-dithienylbenzotriazole, 2,3-bis(4-octyloxyphenyl)quinoxaline, and 5,8-bis(thiophen- 2-yl)-2,3-bis(4-octyloxyphenyl)quinoxaline and 1,4-diketo-2,5-di(2-ethylhexyl)-3,6-diphenyl- pyrrolopyrrole, respectively, were successfully synthesized as new polymeric donors in BHJ PVCs. We found that the Voc of the devices varied inversely with the HOMO level of the electron donor materials. Compared with the chemical structure of the copolymers PBDT-BTA and PBDT-DTBTA, the additional thiophene unit could decrease the effect conjugated length of the copolymer, which results in low-lying HOMO level of the copolymer and higher Voc of the devices based on this copolymer. Similarly, the effect of thiophene spacer also works on the couple of copolymer PBDT-Q and PBDT-DTQ. In contrast with the device based on copolymer PBDT-PhDPP using Al as cathode, the bilayer cathodes such as PFN/Al, LiF/Al and Ca/Al could improve the Voc, of which the highest Voc value is obtained from the PFN/Al cathode.
In chapter 5, for the first time, two quinoxaline-based copolymers PPN-p-DTQ and PPN-m-DTQ, with the different substitutions of octyloxy groups and phenanthrene as electron-donating segment, were successfully synthesized as new polymeric donors in polymer solar cells. The octyloxy substituents added to the para position of the phenyl rings on the quinoxaline monomer can push down the HOMO level and the LUMO level of the copolymer, which contrast the case of the copolymer with octyloxy sbustituents on the meta position of the phenyl rings on the quinoxaline unit. Nevertheless the Voc of the devices based on the two copolymers is not consistent with the HOMO level of these copolymers.
本论文是从研究苯并三唑杂环开始,首先合成4,7-二噻吩-2-十二烷基-2,1,3-苯并三唑单体,并与常见的给电子单元芴,咔唑和烷氧基苯通过Suzuki缩聚反应得到三个交替聚合物PF-DTBTA, PCz-DTBTA和PPh-DTBTA。当聚合物与受体PCBM的共混比为1:2时,对于聚合物PF-DTBTA、PCz-DTBTA和PPh-DTBTA作为给体并且Al作为阴极的器件来说,电池效率分别是0.9%,1.51%和1.16%。当用PFN/Al作双层阴极时,如果相对于Al作为阴极开路电压有损失就会被恢复弥补。对于苯并三唑类聚合物,当阴极是PFN和Al双层时,由于苯并三唑类给体聚合物和PFN层有N-N相互作用,短路电流和填充因子会有相应的提高;从而对于聚合物PF-DTBTA、PCz-DTBTA和PPh-DTBTA作为电子给体说,相应的电池效率可以提高到1.3%, 2.75%和1.39%。电池效率提高最多的是聚合物PCz-DTBTA作为给体的器件,增幅有80%,这暂时归因于是咔唑单元和PFN层有额外的氮-氮相互作用。这些结果对研究电池器件界面修饰来说是有用的。我们的结果也表明双层阴极是有提高太阳电池效率的潜力的。
第三章合成了一系列芴和二噻吩苯并三唑单元共聚的聚合物获得高效黄光,橙光和白光聚合物发光二极管。共聚物PF-DTBTA0.03?15是无规聚合物,而共聚物PF-DTBTA50是交替聚合物。八个能量转移型共聚物的薄膜具有高的光致发光外量子效率,在60?72%范围。共聚物PF-DTBTA1?15是黄光聚合物,外量子效率高达5.78%,而共聚物PF-DTBTA50是橙光聚合物,外量子效率约为3.3%。单元DTBTA含量高的交替聚合物PF-DTBTA50获得高的PL效率和外量子效率表明单元DTBTA是在固态PL和EL过程中受低浓度淬灭效应影响的高效发色团。由于从芴链段单元部分能量转移到单元DTBTA,单元DTBTA较低含量的共聚物PF-DTBTA0.03?0.1获得白光电致发光。在白光发光二极管中我们获得了流明效率高达11 cd/A的非掺杂单一白光聚合物。
第四章合成了二噻吩并苯单体,并与苯并三唑,二噻吩苯并三唑,喹喔啉,二噻吩喹喔啉和吡咯并吡咯二酮缺电子单元共聚得到五个交替聚合物PBDT-BTA, PBDT-DTBTA, PBDT-Q, PBDT-DTQ和PBDT-PhDPP。不同聚合物太阳电池器件的开路电压与聚合物的HOMO能级是相反关系。对聚合物PBDT-BTA和PBDT-DTBTA的化学结构进行比较,额外多出的噻吩单元能减少聚合物的有效共轭长度,以至于聚合物的HOMO能降低和相应的开路电压变大。噻吩桥的作用同样对聚合物PBDT-Q也是有效的。聚合物PBDT-PhDPP为给体的器件,使用不同阴极,发现双层阴极可以提高其开路电压,并且PFN/铝阴极提高最多。
第五章首次合成了两种基于烷氧基不同位置取代的喹喔啉的菲共聚物,作为聚合物给体材料应用在体异质结聚合物太阳电池。对比对位取代和间位取代,对位取代的聚合物可以拉低聚合物的HOMO能级和LUMO能级。尽管如此,聚合物器件开路电压却不是相同的结果,对位取代的反而高些。器件结果表明对位烷氧基取代苯的喹喔啉聚合物PPN-p-DTQ与PCBM共混比为1:2的器件开路电压比相同共混比例下的间位烷氧基取代苯的喹喔啉聚合物PPN-m-DTQ的较低一点,然而在共混比为1:4,器件开路电压的情况相反。
Conjugated polymers are widely utilized in organic semiconductor device due to their excellent environmental stability, thermal stability, diversity, processability and interesting optoelectronic properties. Incorporating heterocycles into conjugated polymers could induce the change of electronic properties of conjugated polymers, and different optoelectronic properties, which are candidates for polymer light-emitting diodes, polymer field-effect-transistor and polymer solar cells. Heterocycle-based copolymers as the active layer can emit red, green, blue and white light in OLED. Copolymers of heterocycle compounds as electron-poor unit and electron-rich unit as comonomer are widely used in BHJ PVCs to match the spectra of solar photons and effectively utilize it.
In the beginning, this dissertation is focusing on the optoelectronic properties of benzotriazole unit. In chapter 2, three BTA-based conjugated polymers PF-DTBTA, PCz-DTBTA, and PPh-DTBTA, with electron-donating segments of fluorene, carbazole, and dialkoxybenzene respectively, were successfully synthesized as new polymeric donors in BHJ PVCs. Using PFN/Al bilayer cathode could elevate Voc if Voc loss was encountered when using Al cathode. Using PFN/Al bilayer cathode could also improve Isc and FF for the three BTA-based copolymers, from which N-N interactions between the BTA-based polymers and the PFN were proposed. Consequently, PFN/Al bilayer cathode elevated PCE values. The most significant increasing of PCE with a calculated value of 80% was found for PCz-DTBTA as the donor, and this might be related to the additional N-N interactions between the carbazole segments and the PFN. The results would supply useful information to understand the contribution of an interfacial layer on the photovoltaic performances. Our results also suggest that the bilayer cathode would have great potential to elevate PCE of BHJ PVCs.
In chapter 3, a series of conjugated polymers PF-DTBTA derived from 2,7-fluorene and 4,7-dithienylbenzotriazole (DTBTA) were developed for high efficiency PLEDs with multi-colors of yellow, orange, and white lights. The PF-DTBTA0.03?15 are random copolymers while the PF-DTBTA50 is an alternating copolymer. PF-DTBTA1?15 showed yellow EL with EQEmax up to 5.78% while PF-DTBTA50 displayed orange EL with EQEmax of 3.3%. The highΦPL and EQEmax of PF-DTBTA50 with very high DTBTA content indicate that DTBTA is a high efficiency chromophore with very low concentration quenching effects in the solid state PL and EL processes. Introducing very low DTBTA contents in PF-DTBTA0.03?0.1 achieved white EL due to partial energy transfer from fluorene segments to the DTBTA units. WPLEDs with maximum luminous efficiency (LEmax) up to 11 cd/A could be realized from the non-doped single-polymer.
In chapter 4, five BDT-based conjugated polymers PBDT-BTA, PBDT-DTBTA, PBDT-Q, PBDT-DTQ, and PBDT-PhDPP, with electron-accepting segments of benzotriazole, 4,7-dithienylbenzotriazole, 2,3-bis(4-octyloxyphenyl)quinoxaline, and 5,8-bis(thiophen- 2-yl)-2,3-bis(4-octyloxyphenyl)quinoxaline and 1,4-diketo-2,5-di(2-ethylhexyl)-3,6-diphenyl- pyrrolopyrrole, respectively, were successfully synthesized as new polymeric donors in BHJ PVCs. We found that the Voc of the devices varied inversely with the HOMO level of the electron donor materials. Compared with the chemical structure of the copolymers PBDT-BTA and PBDT-DTBTA, the additional thiophene unit could decrease the effect conjugated length of the copolymer, which results in low-lying HOMO level of the copolymer and higher Voc of the devices based on this copolymer. Similarly, the effect of thiophene spacer also works on the couple of copolymer PBDT-Q and PBDT-DTQ. In contrast with the device based on copolymer PBDT-PhDPP using Al as cathode, the bilayer cathodes such as PFN/Al, LiF/Al and Ca/Al could improve the Voc, of which the highest Voc value is obtained from the PFN/Al cathode.
In chapter 5, for the first time, two quinoxaline-based copolymers PPN-p-DTQ and PPN-m-DTQ, with the different substitutions of octyloxy groups and phenanthrene as electron-donating segment, were successfully synthesized as new polymeric donors in polymer solar cells. The octyloxy substituents added to the para position of the phenyl rings on the quinoxaline monomer can push down the HOMO level and the LUMO level of the copolymer, which contrast the case of the copolymer with octyloxy sbustituents on the meta position of the phenyl rings on the quinoxaline unit. Nevertheless the Voc of the devices based on the two copolymers is not consistent with the HOMO level of these copolymers.
引文
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