基于S，S-二氧—二苯并噻吩单元共聚物的合成及光电性能
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摘要
S,S-二氧-二苯并噻吩是一个缺电子单元，具有较高的电子亲和势和比芴单元稍小的带隙，有利于电子的注入和传输。
本论文合成了新型的D-A-D结构的S,S-二氧-二苯并噻吩的衍生物，通过Suzuki反应将其引入到聚芴主链中制备了绿光发射的共聚物。聚合物具有优良的热稳定性；在光致发光过程中，聚合物中会发生从芴链段到窄带隙单元的有效的能量转移；单层器件ITO/PEDOT:PSS/polymer/CsF/Al发射510nm左右的蓝绿光，最大流明效率为6.6cd·A1。通过在主链中引入S,S-二氧-二苯并噻吩单元，聚合物的LUMO能级降低，使电子、空穴的注入和传输更加平衡，器件的效率得以提高，单层器件的最大流明效率为9.0cd·A1，色坐标为(0.27,0.56)。
利用蓝光与橙红光两单元之间不完全能量转移达到白光的原理将发橙红光的2,7-二(5-溴-2-噻吩基)-9-芴酮单体引入聚芴主链，实现了两元光单分子聚合物白光发射，最大流明效率为0.5cd·A1，对应的最大外量子效率为0.2%。再将发蓝光的S,S-二氧-二苯并噻吩引入聚合物主链中，增强了两元光单分子聚合物白光发射，色坐标为(0.34,0.32)，最大流明效率为3.5cd·A1，对应的最大外量子效率为1.5%。此白光器件的EL光谱不仅在很大的电流密度范围内保持不变，且其流明效率随着电流密度的增加下降缓慢，表现了优异的光谱稳定性。S,S-二氧-二苯并噻吩的引入降低了聚合物的LUMO能级，有利于电子的注入和传输，从而提高了器件的EL效率。
制备了3,6-咔唑和2,8-二辛氧基-S,S-二氧-二苯并噻吩的交替共聚物以及2,8-二辛氧基-S,S-二氧-二苯并噻吩的均聚物。其中，交替共聚物的电致发光器件发天蓝光，最大流明效率和外量子效率分别为0.78cd·A1和0.6%。由于带隙很宽，可用作红色磷光材料的主体材料。2,8-二辛氧基-S,S-二氧-二苯并噻吩的均聚物也是一类带隙很宽的聚合物材料(Eg=3.10eV)，具有作主体材料的潜力。
合成了一系列醇溶性的主链含有2,8-二辛氧基-S,S-二氧-二苯并噻吩单元、侧链含有胺基或二乙醇胺基的中性聚芴衍生物。侧链上胺基或二乙醇胺基的存在使得这类聚合物在甲醇中(加有痕量乙酸)具有良好的溶解性；它们的紫外-可见吸收光谱、光致发光光谱和能带结构主要由共聚物主链决定；它们的LUMO/HOMO比具有类似结构、但主链中不含2,8-二辛氧基-S,S-二氧-二苯并噻吩单元、最近被广泛使用的电子注入材料聚[9,9-二辛基芴-9,9-双(N,N-二甲基丙基)芴](PFN)的低。我们将这类聚合物成功地作为电子注入材料运用于多层的荧光聚合物电致发光二极管和聚合物太阳能电池器件中。以P-PPV为发光层，以制备的聚合物配合Al电极为复合阴极的绿色荧光PLED器件的效率比单纯Al阴极器件的效率高得多，与Ba/Al和PFN/Al阴极器件的效率相当或更高。其中，最佳的流明效率为22.1cd·A1(EQE=7.9%)，是单纯Al器件效率(LEmax=0.3cd·A1,EQE=0.1%)的74倍，是Ba/Al阴极器件效率(LEmax=11.9cd·A1, EQE=4.3%)的1.9倍，是PFN/Al阴极器件效率(LEmax=14.5cd·A1，EQE=5.0%)的1.5倍。以PFO-DBT35:PCBM=1:2为活性层、聚合物为电子注入层与铝配合制备的聚合物太阳能电池器件呈现出比铝阴极器件高得多的器件效率，与PFN/Al阴极器件的效率相当或更高。其中，最佳的器件效率是单纯铝阴极器件效率的1.6倍，是PFN/Al阴极器件效率的1.2倍。由于胺基或二乙醇胺基与铝电极之间的相互作用在金属电极/活性层界面之间形成偶极子导致的升高的开路电压证实了插入制备的聚合物作为电子注入层可以降低从铝电极的电子注入势垒；而且，由于制备的聚合物较深的LUMO/HOMO能级使得电子注入改善而导致的更高的电流以及被阻挡的空穴传输，使得电荷注入传输更加平衡，因此效率得以提高。主链和侧链结构均对材料的电子注入能力有影响。优良的器件效率、改善的电子注入以及在环境友好溶剂中独特的溶解性使得制备的聚合物成为一类有潜力的电子注入材料。
Dibenzothiophene-S,S-dioxide (SO) is an n-type aromatic heterocycle moiety, whichpocesses high fluorescence efficiency, electron affinity energy and electron-transportingproperties.
Green light-emitting polyfluorenes were synthesized by Suzuki polycondensation viaintroducing dibenzothiophene-S,S-dioxide-(di-)tri-phenylamine moieties of D-A-D structureand dibenzothiophene-S,S-dioxide unit into the polyfluorene backbone. The copolymers showa high thermal stability; the efficient energy transfer from fluorene segments to low-band-gapunits occurred in the PL process; and the EL emission peaked at about510nm wasexclusively from the low-band-gap units. The lowest unoccupied molecular orbital (LUMO)levels reduce with increasing the SO unit content in the polymers. Incorporating SO unit intothe polymer backbone makes the device performances improved. The maximal luminousefficiency of9.0cd·A-1with the CIE coordinate of (0.27,0.56) was obtained based on asingle-layered device of ITO/PEDOT:PSS/polymer/CsF/Al. And the polymers exhibiteddramatic LE stability at high current densities. SO unit lowers the LUMO level, balances theinjection and transportation of both electron and hole in the polymers, and therefore improvesthe device performances.
Novel white-emitting polyfluorenes were synthesized by intruducing2,7-bis(2-thienyl)fluoren-9-one unit into backbones. Then dibenzothiophene-S,S-dioxide unit was introduced intobackbones to obtain white-emitting polyfluorenes. Dibenzothiophene-S,S-dioxide possessesstrong electron-withdrawing ability and can improve the device performances. The bestdevice performanes are a maximum luminous efficiency (LE) of3.5cd·A1, a maximumluminance of9298cd/m2and a CIE coordinate of (0.34,0.32) with the configuration:ITO/PEDOT/PVK/polymer/CsF/Al.
The alternating copolymer of2,8-bis(octyloxy)-dibenzothiophene-S,S-dioxide and3,6-carbazole and homopolymer of2,8-bis(octyloxy)-dibenzothiophene-S,S-dioxide weresynthesized. The alternating polymer exhibited the LEmaxand EQEmaxof0.78cd·A1and0.6%, respectively. And both of the polymers have the potential to act as host materialsbecause of their large band gaps.
A series of novel neutral amino-and diethanolamino-functionalized polyfluorenederivatives with various ratios of2,8-bis(octyloxy)-dibenzothiophene-S,S-dioxide ascomonomers were synthesized and utilized as electron-injection layer (EIL) in combinationwith high-work-function Al electrode in polymer light-emitting diodes (PLEDs) and polymer solar cells (PSCs). The UV-vis absorption and photoluminescence properties of these novelpolymers are mainly determined by the conjugated main chains. The polymers possess deeperLUMO/HOMO levels than often-used EIL material poly[(9,9-bis(3’-(N,N-dimethylamino)propyl)-2,7-fluorene)-alt-2,7-(9,9-dioctylfluorene)](PFN). These acid-assisted alcohol-soluble polymers can be used as EILs in combination with Al electrode to fabricate P-PPVPLEDs with device performances significantly higher than bare Al cathode device,comparable to or exceeding well-known Ba/Al cathode device and even PFN/Al cathodedevice. Among them, the best device performances are74times higher maximum luminousefficiency (LEmax=22.1cd·A1, EQE=7.9%) than that of bare Al cathode device (LEmax=0.3cd·A1, EQE=0.1%),1.9times higher than that of Ba/Al cathode device (LEmax=11.9cd·A1,EQE=4.3%) and1.5times higher than that of PFN/Al cathode device (LEmax=14.5cd·A1,EQE=5.0%). The PFO-DBT35:PCBM PSCs based on Al cathode with these novel polymersas EILs also show excellent device performances higher than Al cathode device, comparableto or exceeding PFN/Al cathode device. Among them, the best power conversion efficiency(PCE) is1.6times higher than that of bare Al cathode device and1.2times higher than that ofPFN/Al cathode device. The enhanced open-circuit voltages (Vocs) clarified that the electroninjection barrier from the Al electrode can be lowered by inserting the novel polymers as EILs.Moreover, the improvement of electron injection in combination with hole-blocking due tothe deep LUMO/HOMO levels of these novel polymers with the introduction of2,8-bis(octyloxy)-dibenzothiophene-S,S-dioxide unit into polymer backbones brings about theflux of charge carriers balanced, leading to an increase in efficiency. The characteristics ofboth main chain structures and pendant polar groups of these polymers have influence on theirelectron-injecting ability. The good device performances, the enhanced electron injectionfrom air-stable high-work-function metal Al in combination with hole-blocking and theunique solubility in environmentally friendly solvents make the novel polymers in this studypromising candidates as a new type of EIL materials for highly efficient PLEDs and PSCswith high-work-function Al electrode.
本论文合成了新型的D-A-D结构的S,S-二氧-二苯并噻吩的衍生物，通过Suzuki反应将其引入到聚芴主链中制备了绿光发射的共聚物。聚合物具有优良的热稳定性；在光致发光过程中，聚合物中会发生从芴链段到窄带隙单元的有效的能量转移；单层器件ITO/PEDOT:PSS/polymer/CsF/Al发射510nm左右的蓝绿光，最大流明效率为6.6cd·A1。通过在主链中引入S,S-二氧-二苯并噻吩单元，聚合物的LUMO能级降低，使电子、空穴的注入和传输更加平衡，器件的效率得以提高，单层器件的最大流明效率为9.0cd·A1，色坐标为(0.27,0.56)。
利用蓝光与橙红光两单元之间不完全能量转移达到白光的原理将发橙红光的2,7-二(5-溴-2-噻吩基)-9-芴酮单体引入聚芴主链，实现了两元光单分子聚合物白光发射，最大流明效率为0.5cd·A1，对应的最大外量子效率为0.2%。再将发蓝光的S,S-二氧-二苯并噻吩引入聚合物主链中，增强了两元光单分子聚合物白光发射，色坐标为(0.34,0.32)，最大流明效率为3.5cd·A1，对应的最大外量子效率为1.5%。此白光器件的EL光谱不仅在很大的电流密度范围内保持不变，且其流明效率随着电流密度的增加下降缓慢，表现了优异的光谱稳定性。S,S-二氧-二苯并噻吩的引入降低了聚合物的LUMO能级，有利于电子的注入和传输，从而提高了器件的EL效率。
制备了3,6-咔唑和2,8-二辛氧基-S,S-二氧-二苯并噻吩的交替共聚物以及2,8-二辛氧基-S,S-二氧-二苯并噻吩的均聚物。其中，交替共聚物的电致发光器件发天蓝光，最大流明效率和外量子效率分别为0.78cd·A1和0.6%。由于带隙很宽，可用作红色磷光材料的主体材料。2,8-二辛氧基-S,S-二氧-二苯并噻吩的均聚物也是一类带隙很宽的聚合物材料(Eg=3.10eV)，具有作主体材料的潜力。
合成了一系列醇溶性的主链含有2,8-二辛氧基-S,S-二氧-二苯并噻吩单元、侧链含有胺基或二乙醇胺基的中性聚芴衍生物。侧链上胺基或二乙醇胺基的存在使得这类聚合物在甲醇中(加有痕量乙酸)具有良好的溶解性；它们的紫外-可见吸收光谱、光致发光光谱和能带结构主要由共聚物主链决定；它们的LUMO/HOMO比具有类似结构、但主链中不含2,8-二辛氧基-S,S-二氧-二苯并噻吩单元、最近被广泛使用的电子注入材料聚[9,9-二辛基芴-9,9-双(N,N-二甲基丙基)芴](PFN)的低。我们将这类聚合物成功地作为电子注入材料运用于多层的荧光聚合物电致发光二极管和聚合物太阳能电池器件中。以P-PPV为发光层，以制备的聚合物配合Al电极为复合阴极的绿色荧光PLED器件的效率比单纯Al阴极器件的效率高得多，与Ba/Al和PFN/Al阴极器件的效率相当或更高。其中，最佳的流明效率为22.1cd·A1(EQE=7.9%)，是单纯Al器件效率(LEmax=0.3cd·A1,EQE=0.1%)的74倍，是Ba/Al阴极器件效率(LEmax=11.9cd·A1, EQE=4.3%)的1.9倍，是PFN/Al阴极器件效率(LEmax=14.5cd·A1，EQE=5.0%)的1.5倍。以PFO-DBT35:PCBM=1:2为活性层、聚合物为电子注入层与铝配合制备的聚合物太阳能电池器件呈现出比铝阴极器件高得多的器件效率，与PFN/Al阴极器件的效率相当或更高。其中，最佳的器件效率是单纯铝阴极器件效率的1.6倍，是PFN/Al阴极器件效率的1.2倍。由于胺基或二乙醇胺基与铝电极之间的相互作用在金属电极/活性层界面之间形成偶极子导致的升高的开路电压证实了插入制备的聚合物作为电子注入层可以降低从铝电极的电子注入势垒；而且，由于制备的聚合物较深的LUMO/HOMO能级使得电子注入改善而导致的更高的电流以及被阻挡的空穴传输，使得电荷注入传输更加平衡，因此效率得以提高。主链和侧链结构均对材料的电子注入能力有影响。优良的器件效率、改善的电子注入以及在环境友好溶剂中独特的溶解性使得制备的聚合物成为一类有潜力的电子注入材料。
Dibenzothiophene-S,S-dioxide (SO) is an n-type aromatic heterocycle moiety, whichpocesses high fluorescence efficiency, electron affinity energy and electron-transportingproperties.
Green light-emitting polyfluorenes were synthesized by Suzuki polycondensation viaintroducing dibenzothiophene-S,S-dioxide-(di-)tri-phenylamine moieties of D-A-D structureand dibenzothiophene-S,S-dioxide unit into the polyfluorene backbone. The copolymers showa high thermal stability; the efficient energy transfer from fluorene segments to low-band-gapunits occurred in the PL process; and the EL emission peaked at about510nm wasexclusively from the low-band-gap units. The lowest unoccupied molecular orbital (LUMO)levels reduce with increasing the SO unit content in the polymers. Incorporating SO unit intothe polymer backbone makes the device performances improved. The maximal luminousefficiency of9.0cd·A-1with the CIE coordinate of (0.27,0.56) was obtained based on asingle-layered device of ITO/PEDOT:PSS/polymer/CsF/Al. And the polymers exhibiteddramatic LE stability at high current densities. SO unit lowers the LUMO level, balances theinjection and transportation of both electron and hole in the polymers, and therefore improvesthe device performances.
Novel white-emitting polyfluorenes were synthesized by intruducing2,7-bis(2-thienyl)fluoren-9-one unit into backbones. Then dibenzothiophene-S,S-dioxide unit was introduced intobackbones to obtain white-emitting polyfluorenes. Dibenzothiophene-S,S-dioxide possessesstrong electron-withdrawing ability and can improve the device performances. The bestdevice performanes are a maximum luminous efficiency (LE) of3.5cd·A1, a maximumluminance of9298cd/m2and a CIE coordinate of (0.34,0.32) with the configuration:ITO/PEDOT/PVK/polymer/CsF/Al.
The alternating copolymer of2,8-bis(octyloxy)-dibenzothiophene-S,S-dioxide and3,6-carbazole and homopolymer of2,8-bis(octyloxy)-dibenzothiophene-S,S-dioxide weresynthesized. The alternating polymer exhibited the LEmaxand EQEmaxof0.78cd·A1and0.6%, respectively. And both of the polymers have the potential to act as host materialsbecause of their large band gaps.
A series of novel neutral amino-and diethanolamino-functionalized polyfluorenederivatives with various ratios of2,8-bis(octyloxy)-dibenzothiophene-S,S-dioxide ascomonomers were synthesized and utilized as electron-injection layer (EIL) in combinationwith high-work-function Al electrode in polymer light-emitting diodes (PLEDs) and polymer solar cells (PSCs). The UV-vis absorption and photoluminescence properties of these novelpolymers are mainly determined by the conjugated main chains. The polymers possess deeperLUMO/HOMO levels than often-used EIL material poly[(9,9-bis(3’-(N,N-dimethylamino)propyl)-2,7-fluorene)-alt-2,7-(9,9-dioctylfluorene)](PFN). These acid-assisted alcohol-soluble polymers can be used as EILs in combination with Al electrode to fabricate P-PPVPLEDs with device performances significantly higher than bare Al cathode device,comparable to or exceeding well-known Ba/Al cathode device and even PFN/Al cathodedevice. Among them, the best device performances are74times higher maximum luminousefficiency (LEmax=22.1cd·A1, EQE=7.9%) than that of bare Al cathode device (LEmax=0.3cd·A1, EQE=0.1%),1.9times higher than that of Ba/Al cathode device (LEmax=11.9cd·A1,EQE=4.3%) and1.5times higher than that of PFN/Al cathode device (LEmax=14.5cd·A1,EQE=5.0%). The PFO-DBT35:PCBM PSCs based on Al cathode with these novel polymersas EILs also show excellent device performances higher than Al cathode device, comparableto or exceeding PFN/Al cathode device. Among them, the best power conversion efficiency(PCE) is1.6times higher than that of bare Al cathode device and1.2times higher than that ofPFN/Al cathode device. The enhanced open-circuit voltages (Vocs) clarified that the electroninjection barrier from the Al electrode can be lowered by inserting the novel polymers as EILs.Moreover, the improvement of electron injection in combination with hole-blocking due tothe deep LUMO/HOMO levels of these novel polymers with the introduction of2,8-bis(octyloxy)-dibenzothiophene-S,S-dioxide unit into polymer backbones brings about theflux of charge carriers balanced, leading to an increase in efficiency. The characteristics ofboth main chain structures and pendant polar groups of these polymers have influence on theirelectron-injecting ability. The good device performances, the enhanced electron injectionfrom air-stable high-work-function metal Al in combination with hole-blocking and theunique solubility in environmentally friendly solvents make the novel polymers in this studypromising candidates as a new type of EIL materials for highly efficient PLEDs and PSCswith high-work-function Al electrode.
引文
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