具有电荷传输特性的有机功能材料的合成及其光电性能
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摘要
近30年以来，基于有机化合物的共轭的聚合物和小分子材料在发光二极管、太阳电池等有机光电领域获得了蓬勃的发展，极大地促进了它们的产业化进程。在这些材料中间，具有电荷传输特性的有机功能材料占据着至关重要的地位。为此，本论文着重研究具有电荷传输特性的有机功能材料及其器件性能，具体涉及发光聚合物，基于有机小分子的主体材料和电子传输材料（ETMs）。
在第二章，我们通过引入三芴-2-基胺作为构筑单元，设计合成出具有高的最高占有分子轨道（HOMO）能级的蓝色发光共轭聚合物。通过在三芴-2-基胺基团中引入各种取代基团作为悬坠，有效地将这些聚合物的发光颜色从深蓝色调节到天蓝色区域。在不使用任何空穴传输层（HTL）的情况下，以P4FNCz作为发光层（EML）的器件实现了深蓝色发光，最大的电流效率（CEmax）达到2.44cd/A，对应的外量子效率（EQE）达到3.00%，色坐标为（0.16，0.12）。由于改进了空穴的注入和传输能力，通过使用P4FNCz作为一层HTL，我们成功地制作出了红光和绿光器件，CEmax分别达到7和25cd/A，色坐标分别为（0.64，0.34）和（0.29，0.64），均接近于基于常用的4,4’-双（N-（1-萘基）-N-苯基胺）联苯（NPB）作为HTL的器件。而且，红、绿、蓝三种器件的发光颜色的色坐标非常接近于国家电视标准委员会（NTSC）（美国）和高清电视（HDTV）的标准色坐标。我们通过使用不同的电子传输层（ETL）来调节载流子的复合区域而实现的红绿蓝器件有助于基于聚合物的全彩平板显示的发展。
在第三章，为了提高三芴-2-基胺共轭聚合物的电子传输能力，我们通过共聚的方式在聚合物的主链引入了一种被证明具有优异的电子注入和传输性质的S,S-二氧-二苯并噻吩作为缺电子单元。我们通过控制单体的投料比，有效地抑制分子内的电荷转移（ICT）相互作用，得到了一系列蓝色发光的共轭共聚物。这些聚合物具有优异的热稳定性，合适的最低未占有分子轨道（LUMO）和HOMO能级，其中以PSFOFN15作为EML的单层蓝光器件，表现出最高的亮度（11749cd/m2）和CEmax（2.28cd/A）。而且，所有器件的的色坐标均靠近深蓝光区域，表明这些聚合物在全彩显示和白光照明方面具有潜在的应用前景。
在第四章，为了进一步研究这类聚合物的电荷传输特性，我们从改变聚合物的主链结构入手，把给电性的三芴-2-基胺构筑单元换成电中性的1,3,5-三芴-2-基苯，再变成吸电性的2,4,6-三芴-2-基三嗪，成功地合成了一系列发光的共轭聚合物，深入研究了它们的结构与性质的关系。含有吸电性的骨架和给电性的悬坠的聚合物P1由于强烈的ICT相互作用，在溶液中的光物理性质强烈地依赖于溶剂的极性。我们通过改变聚合物的主链结构以及三芴-2-基胺，1,3,5-三芴-2-基苯和2,4,6-三芴-2-基三嗪中的取代基有效地调节了它们的发光颜色和能级。其中，基于2,4,6-三芴-2-基三嗪的以第二代树枝状咔唑为悬坠的P1d作为EML的深蓝色发光器件，CEmax达到1.26cd/A，相应的EQE为1.27%，色坐标为（0.16，0.14）。相比之下，由于强烈的ICT相互作用，尽管主链和支链都发蓝光，基于2,4,6-三芴-2-基三嗪的以双（9,9-二辛基-9H-芴-2-基）胺为悬坠的P1c作为EML的器件，CEmax达到4.10cd/A，相应的EQE为2.45%，色坐标为（0.24，0.51）。
在第五章，我们发展和丰富了小分子主体材料的种类，首次将1,2,4-噁二唑单元引入到溶液加工型的小分子主体材料，深入地研究了它们的热学、光物理和电化学性质。这些材料可以有效地抑制能量的反转，保证磷光器件的发光全部来自客体材料的发光。通过单载流子器件我们发现含有强亲电性的1,3,4-噁二唑环的134OXD具有良好的电子传输能力，相比之下，由于1,2,4-噁二唑环相对较弱的共轭性和亲电性，含有该单元的主体材料更倾向于传输空穴。以双（4,6-二氟苯基吡啶-N,C2）吡啶甲酰合铱（FIrpic）为客体，134OXD为主体的溶液加工型蓝色磷光器件中，最大亮度达到14994cd/m2，CEmax达到8.75cd/A。在以三[2-（对甲苯基）吡啶]合铱(III)[Ir(mppy)3]为客体的溶液加工型单层绿色磷光器件中，基于134OXD为主体的器件最大亮度为9158cd/m2，CEmax达到12.55cd/A。
在第六章，我们发展了一系列含有吡啶单元的ETMs作为基于FIrpic的蓝色磷光器件的ETL。通过在分子的骨架和周边引入具有不同氮原子取向的吡啶环，有效地调控了这些ETMs的能级。我们仅仅通过调控那些吡啶环的氮原子取向就极大地降低了器件的工作电压却又不影响EQE。我们实现了器件在1和100cd/m2的亮度下极其低的工作电压（2.61和3.03V），并得到了迄今为止最高的65.8和59.7lm/W的功率效率（PE），和EQE（24.4和25.7%）。而且，我们通过选用低单线态-三线态交换能的主体材料，器件在100cd/m2的亮度下的工作电压可被进一步降低至2.70V，发光的门槛电压甚至比理论最小值（光子能量/电荷）还低了0.2-0.3V。除了降低工作电压，通过联合合适的主体材料，器件的效率滚降可进一步降低。我们的工作表明这些材料在移动设备和有机照明等高功率消耗领域有着很大的应用前景。
在第七章，我们通过Suzuki偶联反应成功地合成了一系列三唑和吡啶杂化的ETMs，我们发现它们的HOMO和LUMO能级强烈地依赖于苯环的连接位置和数量。由于在分子的周边引入了强亲电性的吡啶环，相比于被广泛使用的[3-（联苯基-4-基）-5-（4-叔丁基苯基）-4-苯基-4H-1,2,4-三唑]（TAZ），它们的电子注入/传输能力得到了极大地改进。通过把这些分子作为绿色磷光器件的ETL和空穴/激子阻挡层，器件的驱动电压得到了极大地降低。由于基于TPyTAZm的器件具有匹配的能级，较高的电子传输能力，以及平衡的载流子复合，相应的器件表现出最高的效率，最大的PE达到72.2lm/W（73.6cd/A，21.8%）。相比于TAZ的器件，由于TPyTAZm更好的三线态激子限制能力，效率滚降得到进一步地下降，在100和1000cd/m2的实际亮度下，PE仍达到58.3和42.3lm/W。我们的工作有助于推动基于三唑的ETMs的分子设计以进一步提高磷光OLEDs的性能。
在第八章，我们成功地设计并合成了一系列基于缺电子的吡啶鎓盐的水/醇溶小分子，深入地研究了它们的光物理和电化学性质。由于F8PS具有最好的成膜能力，我们把它作为聚合物太阳电池（PSCs）的ETL。与基于纯铝的器件相比，通过在活性层聚[N-9’-庚癸基-2,7-咔唑-交替-5,5-（4’,7’-二-2-噻吩基-2’,1’,3’-苯并噻二唑）]（PCDTBT）：[6,6]-苯基-C71-丁酸甲基酯（PC71BM）和金属阴极之间引入一层超薄的F8PS作为ETL，器件的开路电压（Voc），短路电流（Jsc）和填充因子（FF）同时得到了增加，使得能量转换效率（PCE）从最初的4.32%提升到6.56%。这么高的Voc值（0.94V）是文献中迄今为止基于PCDTBT:PC71BM为活性层的PSCs的最好结果之一。而Voc的提高可能是由于F8PS产生的界面偶极所引起的。同时，通过乙醇处理活性层，器件的PCE可从4.32%提升到5.55%。因此，沉积吡啶鎓盐后器件性能的增强可能是乙醇处理和缺电子的吡啶鎓盐层的共同作用。亲水的吡啶鎓盐衍生物具有的良好的水/醇溶解性，理想的HOMO/LUMO能级，优异的电子传输能力，是有机光电器件领域一类有潜力的溶液加工型ETMs。
Conjugated polymers and small molecules based on organic compounds have obtainedvigorous development in organic optoelectronic fields such as light-emitting diodes and solarcells during the past three decades, which greatly accelerates the industrialization process oftheirs. Among these, organic functional materials with charge-transfer characteristic playcrucial role. Therefore, in this thesis, I focus on the study of organic functional materials withcharge-transfer characteristic as well as device performance of theirs, including light-emittingpolymers, host materials and electron-transport materials (ETMs) based on organic smallmolecules.
In chapter2, a series of blue-light-emitting conjugated polymers that possess high-lying thehighest occupied molecular orbital (HOMO) energy levels were designed and synthesized byintroducing trifluoren-2-yl-amine (TFA) as a building block. The emission color could beeffectively tuned in the region of deep-blue and light-blue by introducing various substituentsonto the TFA as the pendants. Deep-blue light emission was achieved for the device based onP4FNCz as an emitting layer (EML) without using any hole-transport layer (HTL), giving amaximum current efficiency (CEmax) of2.44cd/A, corresponding to external quantumefficiency (EQE) of3.00%, with Commission Internationale de L’Eclairage (CIE) coordinatesof (0.16,0.12). Thanks to the improved hole injection and transport ability, red-andgreen-light-emitting devices based on P4FNCz as a HTL were also successfully fabricated,giving CEmaxof7and25cd/A with CIE coordinates of (0.64,0.34) and (0.29,0.64),respectively, which are comparable to those of the devices based on a general HTL of4,4’-bis(N-(1-naphthyl)-N-phenylamino)biphenyl (NPB). The CIE coordinates of the RGBdevices are very close to those of the National Television System Committee (NTSC)(USA)and High Definition Television (HDTV) standard colors. The RGB devices achieved by tuningthe carrier recombination zone with different electron-transport layers (ETL) will facilitate thedevelopment of the polymer-based full-color flat-panel displays in an alternative process.
In chapter3, to improve the electron-transport ability of the conjugated polymers based on TFA, electron-deficient S,S-dioxide-dibenzothiophene unit with excellent electron-inject andtransport property was introduced into the main chain by copolymerization. A series of bluelight-emitting conjugated polymers were obtained through the regulation of feed radio of theirmonomers due to effectively restrain the intramolecular charge-transfer (ICT) interaction.These polymers possess excellent thermal stability, favourable the lowest unoccupiedmoleculer orbital (LUMO) and HOMO energy levels, among them, single-layer blue devicebased on PSFOFN15as an EML showed the maximum luminance of11749cd/m2and CEmaxof2.28cd/A. Moreover, the CIE coordinates of all the devices are very close to the deep blueregion. This suggests the potential applications of these polymers in full-color flat-paneldisplays and white lighting.
In chapter4, to further investigate the charge-transport charactristic of these types ofpolymers, electron-donating TFA building blocks of main chains were replaced by electricallyneutral1,3,5-trifluoren-2-ylbenzene (TFB), and electron-withdrawing2,4,6-trifluoren-2-yltriazine (TFT). Their structure-property relationships were thoroughlystudied. For P1containing electron-withdrawing backbone and electron-donating pendants,their photophysical properties in solution are strongly dependent on the solvent polarity due tothe intense ICT interaction. In addition, their emission colors and energy levels could beeffectively tuned by changing the structure of the main chain as well as the substituent at thependent fluorene of TFT, TFB, and TFA. Deep-blue light emission was achieved for the devicebased on P1d, a polymer based on TFT and the second generation (G2) of carbazoledendrimer pendant, that shows a CEmaxof1.26cd/A, corresponding to EQE of1.27%, withCIE coordinates of (0.16,0.14). In comparison, due to the intense ICT interaction between themain chain and the side chain, light-green emission was achieved for the device based on P1c,a polymer based on TFT and bis(9,9-dioctyl-9H-fluoren-2-yl)amine pendant, giving thehighest CEmaxof4.10cd/A, corresponding to EQE of2.45%, with CIE coordinates of (0.24,0.51), although either of the main chain and the side chain emits blue light.
In chapter5,1,2,4-oxadiazole units were firstly introduced into the small molecules basedsolution-processable host materials, and their thermal, photophysical, and electrochemical properties were studied thoroughly. These hosts could effectively suppress the energy fromphosphorescent emitter transfer to the host molecules and thus assuring the emission ofdevices was all from the phosphorescent emitter. The good electron transport capacity of134OXD with strong electron affinity of1,3,4-oxadiazole ring was achieved, in contrast,maybe due to the relatively poorer conjugation and electron affinity of1,2,4-oxadiazole ring,those host materials containing1,2,4-oxadiazole unit were more prone to transport hole basedon the electron/hole only devices. For the iridium(III)bis[(4,6-difluorophenyl)-pyridinate-N,C2’]picolinate (FIrpic)-based blue phosphorescentorganic light-emitting diodes (OLEDs), the devices based on134OXD as host exhibited thehighest maximum luminance of14994cd/m2, and the highest CEmaxof8.75cd/A. For theiridium(III) tris[2-(p-tolyl)pyridine](Ir(mppy)3)-based green phosphorescent devices, thehighest maximum luminance of9158cd/m2, and the highest CEmaxof12.55cd/A wereachieved for134OXD.
In chapter6, a series of pyridine-containing ETMs were developed as an ETL as well as ahole/exciton block layer for FIrpic-based blue phosphorescent OLEDs. The energy levels ofthe ETMs could be finely tuned by the introduction of pyridine rings in the framework and onthe periphery of the molecules. Significantly reduced operating voltage was achieved withoutcompromising EQE by solely tuning the nitrogen atom orientations of those pyidine rings.Unprecedented low operating voltages of2.61and3.03V were realized at1and100cd/m2,giving ever highest power efficiency (PE) values of65.8and59.7lm/W, respectively. Inaddition, the operating voltages at1and100cd/m2could be further reduced to <2.4and2.70V,respectively, by using a host material with a small singlet-triplet exchange energy (ΔEST), andthe threshold voltage for electroluminescence can even be0.2–0.3V lower than the theoreticalminimum value of the photon energy (hv) divided by electron charge (e). Aside from thereduced operating voltage, a further reduced roll-off in efficiency was also achieved by thecombination of an appropriate host material. The current findings make them as potentialcandidates for high-power consumption applications such as in mobile devices and organiclighting.
In chapter7, a series of triazole and pyridine hybrid molecules were successfullysynthesized by typical Suzuki cross-coupling reactions, and their thermal, photophysical andelectrochemical properties are thoroughly studied. Their HOMO and LUMO energy levels arestrongly dependent on the linkage position and the number of benzene ring. By using thesemolecules as an ETL and a hole/exciton-block layer in green phosphorescent OLEDs, muchbetter electron-injection/transport ability was achieved to give significantly reduced drivingvoltage compared with the widely used ETM of[3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole](TAZ) due to theintroduction of strong electrophilic pyridine rings onto the periphery of the molecules. Thedevice based on TPyTAZm exhibits the highest efficiency with a maximum PE up to73.6lm/W (72.2cd/A,21.8%) due to the matched energy level, high electron transport ability, andthus more balanced carrier recombination. In addition, compared with the device based onTAZ, it shows much higher PE of58.3and42.3lm/W at the practical brightness of100and1000cd/m2due to its good triplet exciton confinement ability and reduced efficiency roll-off.The current findings are beneficial to the design of triazole–based ETMs for furtherimprovement of phosphorescent OLEDs.
In chapter8, a series of water/alcohol-soluble small molecules based on electron-deficientpyridinium salt were successfully designed and synthesized. Their photophysical andelectrochemical properties were thoroughly studied. Due to its good film-forming ability,F8PS was employed as an ETL in polymer solar cells (PSCs). Simultaneous enhancements inopen-circuit voltage (Voc), short circuit current density (Jsc), and fill factor (FF) were achieved,and power conversion efficiency (PCE) was increased from4.32%to6.56%compared to thedevice based on the bare Al cathode. Vocwas significantly improved from0.76V to0.94V,and it is one of the best results reported in literature to date for the PSCs based on the activelayer of poly [N-9’-heptadecanyl-2,7-carbazole-alt-5,5-(4’,7’-di-2-thienyl-2’,1’,3’-benzothiadiazole)](PCDTBT):[6,6]-phenyl-C71-butyric acid methylester(PC71BM). The greatly increased Vocmay be due to the interface dipoles generated by F8PS. Itwas also demonstrated that post treatment of the active layer with ethanol, improvement of the overall device efficiency from the initial4.32%to5.55%compared to the device with the bareAl cathode. Therefore, the improvement in performance after pyridinium salt deposition maybe due to a combination of the effects of ethanol treatment and the presence of the thinpyridinium salt layer. The good water/alcohol solubility, ideal HOMO/LUMO energy levels,excellent electron transfer ability of the hydrophilic pyridinium salt derivatives urges them tobe a promising family of solution-processable ETMs.
在第二章，我们通过引入三芴-2-基胺作为构筑单元，设计合成出具有高的最高占有分子轨道（HOMO）能级的蓝色发光共轭聚合物。通过在三芴-2-基胺基团中引入各种取代基团作为悬坠，有效地将这些聚合物的发光颜色从深蓝色调节到天蓝色区域。在不使用任何空穴传输层（HTL）的情况下，以P4FNCz作为发光层（EML）的器件实现了深蓝色发光，最大的电流效率（CEmax）达到2.44cd/A，对应的外量子效率（EQE）达到3.00%，色坐标为（0.16，0.12）。由于改进了空穴的注入和传输能力，通过使用P4FNCz作为一层HTL，我们成功地制作出了红光和绿光器件，CEmax分别达到7和25cd/A，色坐标分别为（0.64，0.34）和（0.29，0.64），均接近于基于常用的4,4’-双（N-（1-萘基）-N-苯基胺）联苯（NPB）作为HTL的器件。而且，红、绿、蓝三种器件的发光颜色的色坐标非常接近于国家电视标准委员会（NTSC）（美国）和高清电视（HDTV）的标准色坐标。我们通过使用不同的电子传输层（ETL）来调节载流子的复合区域而实现的红绿蓝器件有助于基于聚合物的全彩平板显示的发展。
在第三章，为了提高三芴-2-基胺共轭聚合物的电子传输能力，我们通过共聚的方式在聚合物的主链引入了一种被证明具有优异的电子注入和传输性质的S,S-二氧-二苯并噻吩作为缺电子单元。我们通过控制单体的投料比，有效地抑制分子内的电荷转移（ICT）相互作用，得到了一系列蓝色发光的共轭共聚物。这些聚合物具有优异的热稳定性，合适的最低未占有分子轨道（LUMO）和HOMO能级，其中以PSFOFN15作为EML的单层蓝光器件，表现出最高的亮度（11749cd/m2）和CEmax（2.28cd/A）。而且，所有器件的的色坐标均靠近深蓝光区域，表明这些聚合物在全彩显示和白光照明方面具有潜在的应用前景。
在第四章，为了进一步研究这类聚合物的电荷传输特性，我们从改变聚合物的主链结构入手，把给电性的三芴-2-基胺构筑单元换成电中性的1,3,5-三芴-2-基苯，再变成吸电性的2,4,6-三芴-2-基三嗪，成功地合成了一系列发光的共轭聚合物，深入研究了它们的结构与性质的关系。含有吸电性的骨架和给电性的悬坠的聚合物P1由于强烈的ICT相互作用，在溶液中的光物理性质强烈地依赖于溶剂的极性。我们通过改变聚合物的主链结构以及三芴-2-基胺，1,3,5-三芴-2-基苯和2,4,6-三芴-2-基三嗪中的取代基有效地调节了它们的发光颜色和能级。其中，基于2,4,6-三芴-2-基三嗪的以第二代树枝状咔唑为悬坠的P1d作为EML的深蓝色发光器件，CEmax达到1.26cd/A，相应的EQE为1.27%，色坐标为（0.16，0.14）。相比之下，由于强烈的ICT相互作用，尽管主链和支链都发蓝光，基于2,4,6-三芴-2-基三嗪的以双（9,9-二辛基-9H-芴-2-基）胺为悬坠的P1c作为EML的器件，CEmax达到4.10cd/A，相应的EQE为2.45%，色坐标为（0.24，0.51）。
在第五章，我们发展和丰富了小分子主体材料的种类，首次将1,2,4-噁二唑单元引入到溶液加工型的小分子主体材料，深入地研究了它们的热学、光物理和电化学性质。这些材料可以有效地抑制能量的反转，保证磷光器件的发光全部来自客体材料的发光。通过单载流子器件我们发现含有强亲电性的1,3,4-噁二唑环的134OXD具有良好的电子传输能力，相比之下，由于1,2,4-噁二唑环相对较弱的共轭性和亲电性，含有该单元的主体材料更倾向于传输空穴。以双（4,6-二氟苯基吡啶-N,C2）吡啶甲酰合铱（FIrpic）为客体，134OXD为主体的溶液加工型蓝色磷光器件中，最大亮度达到14994cd/m2，CEmax达到8.75cd/A。在以三[2-（对甲苯基）吡啶]合铱(III)[Ir(mppy)3]为客体的溶液加工型单层绿色磷光器件中，基于134OXD为主体的器件最大亮度为9158cd/m2，CEmax达到12.55cd/A。
在第六章，我们发展了一系列含有吡啶单元的ETMs作为基于FIrpic的蓝色磷光器件的ETL。通过在分子的骨架和周边引入具有不同氮原子取向的吡啶环，有效地调控了这些ETMs的能级。我们仅仅通过调控那些吡啶环的氮原子取向就极大地降低了器件的工作电压却又不影响EQE。我们实现了器件在1和100cd/m2的亮度下极其低的工作电压（2.61和3.03V），并得到了迄今为止最高的65.8和59.7lm/W的功率效率（PE），和EQE（24.4和25.7%）。而且，我们通过选用低单线态-三线态交换能的主体材料，器件在100cd/m2的亮度下的工作电压可被进一步降低至2.70V，发光的门槛电压甚至比理论最小值（光子能量/电荷）还低了0.2-0.3V。除了降低工作电压，通过联合合适的主体材料，器件的效率滚降可进一步降低。我们的工作表明这些材料在移动设备和有机照明等高功率消耗领域有着很大的应用前景。
在第七章，我们通过Suzuki偶联反应成功地合成了一系列三唑和吡啶杂化的ETMs，我们发现它们的HOMO和LUMO能级强烈地依赖于苯环的连接位置和数量。由于在分子的周边引入了强亲电性的吡啶环，相比于被广泛使用的[3-（联苯基-4-基）-5-（4-叔丁基苯基）-4-苯基-4H-1,2,4-三唑]（TAZ），它们的电子注入/传输能力得到了极大地改进。通过把这些分子作为绿色磷光器件的ETL和空穴/激子阻挡层，器件的驱动电压得到了极大地降低。由于基于TPyTAZm的器件具有匹配的能级，较高的电子传输能力，以及平衡的载流子复合，相应的器件表现出最高的效率，最大的PE达到72.2lm/W（73.6cd/A，21.8%）。相比于TAZ的器件，由于TPyTAZm更好的三线态激子限制能力，效率滚降得到进一步地下降，在100和1000cd/m2的实际亮度下，PE仍达到58.3和42.3lm/W。我们的工作有助于推动基于三唑的ETMs的分子设计以进一步提高磷光OLEDs的性能。
在第八章，我们成功地设计并合成了一系列基于缺电子的吡啶鎓盐的水/醇溶小分子，深入地研究了它们的光物理和电化学性质。由于F8PS具有最好的成膜能力，我们把它作为聚合物太阳电池（PSCs）的ETL。与基于纯铝的器件相比，通过在活性层聚[N-9’-庚癸基-2,7-咔唑-交替-5,5-（4’,7’-二-2-噻吩基-2’,1’,3’-苯并噻二唑）]（PCDTBT）：[6,6]-苯基-C71-丁酸甲基酯（PC71BM）和金属阴极之间引入一层超薄的F8PS作为ETL，器件的开路电压（Voc），短路电流（Jsc）和填充因子（FF）同时得到了增加，使得能量转换效率（PCE）从最初的4.32%提升到6.56%。这么高的Voc值（0.94V）是文献中迄今为止基于PCDTBT:PC71BM为活性层的PSCs的最好结果之一。而Voc的提高可能是由于F8PS产生的界面偶极所引起的。同时，通过乙醇处理活性层，器件的PCE可从4.32%提升到5.55%。因此，沉积吡啶鎓盐后器件性能的增强可能是乙醇处理和缺电子的吡啶鎓盐层的共同作用。亲水的吡啶鎓盐衍生物具有的良好的水/醇溶解性，理想的HOMO/LUMO能级，优异的电子传输能力，是有机光电器件领域一类有潜力的溶液加工型ETMs。
Conjugated polymers and small molecules based on organic compounds have obtainedvigorous development in organic optoelectronic fields such as light-emitting diodes and solarcells during the past three decades, which greatly accelerates the industrialization process oftheirs. Among these, organic functional materials with charge-transfer characteristic playcrucial role. Therefore, in this thesis, I focus on the study of organic functional materials withcharge-transfer characteristic as well as device performance of theirs, including light-emittingpolymers, host materials and electron-transport materials (ETMs) based on organic smallmolecules.
In chapter2, a series of blue-light-emitting conjugated polymers that possess high-lying thehighest occupied molecular orbital (HOMO) energy levels were designed and synthesized byintroducing trifluoren-2-yl-amine (TFA) as a building block. The emission color could beeffectively tuned in the region of deep-blue and light-blue by introducing various substituentsonto the TFA as the pendants. Deep-blue light emission was achieved for the device based onP4FNCz as an emitting layer (EML) without using any hole-transport layer (HTL), giving amaximum current efficiency (CEmax) of2.44cd/A, corresponding to external quantumefficiency (EQE) of3.00%, with Commission Internationale de L’Eclairage (CIE) coordinatesof (0.16,0.12). Thanks to the improved hole injection and transport ability, red-andgreen-light-emitting devices based on P4FNCz as a HTL were also successfully fabricated,giving CEmaxof7and25cd/A with CIE coordinates of (0.64,0.34) and (0.29,0.64),respectively, which are comparable to those of the devices based on a general HTL of4,4’-bis(N-(1-naphthyl)-N-phenylamino)biphenyl (NPB). The CIE coordinates of the RGBdevices are very close to those of the National Television System Committee (NTSC)(USA)and High Definition Television (HDTV) standard colors. The RGB devices achieved by tuningthe carrier recombination zone with different electron-transport layers (ETL) will facilitate thedevelopment of the polymer-based full-color flat-panel displays in an alternative process.
In chapter3, to improve the electron-transport ability of the conjugated polymers based on TFA, electron-deficient S,S-dioxide-dibenzothiophene unit with excellent electron-inject andtransport property was introduced into the main chain by copolymerization. A series of bluelight-emitting conjugated polymers were obtained through the regulation of feed radio of theirmonomers due to effectively restrain the intramolecular charge-transfer (ICT) interaction.These polymers possess excellent thermal stability, favourable the lowest unoccupiedmoleculer orbital (LUMO) and HOMO energy levels, among them, single-layer blue devicebased on PSFOFN15as an EML showed the maximum luminance of11749cd/m2and CEmaxof2.28cd/A. Moreover, the CIE coordinates of all the devices are very close to the deep blueregion. This suggests the potential applications of these polymers in full-color flat-paneldisplays and white lighting.
In chapter4, to further investigate the charge-transport charactristic of these types ofpolymers, electron-donating TFA building blocks of main chains were replaced by electricallyneutral1,3,5-trifluoren-2-ylbenzene (TFB), and electron-withdrawing2,4,6-trifluoren-2-yltriazine (TFT). Their structure-property relationships were thoroughlystudied. For P1containing electron-withdrawing backbone and electron-donating pendants,their photophysical properties in solution are strongly dependent on the solvent polarity due tothe intense ICT interaction. In addition, their emission colors and energy levels could beeffectively tuned by changing the structure of the main chain as well as the substituent at thependent fluorene of TFT, TFB, and TFA. Deep-blue light emission was achieved for the devicebased on P1d, a polymer based on TFT and the second generation (G2) of carbazoledendrimer pendant, that shows a CEmaxof1.26cd/A, corresponding to EQE of1.27%, withCIE coordinates of (0.16,0.14). In comparison, due to the intense ICT interaction between themain chain and the side chain, light-green emission was achieved for the device based on P1c,a polymer based on TFT and bis(9,9-dioctyl-9H-fluoren-2-yl)amine pendant, giving thehighest CEmaxof4.10cd/A, corresponding to EQE of2.45%, with CIE coordinates of (0.24,0.51), although either of the main chain and the side chain emits blue light.
In chapter5,1,2,4-oxadiazole units were firstly introduced into the small molecules basedsolution-processable host materials, and their thermal, photophysical, and electrochemical properties were studied thoroughly. These hosts could effectively suppress the energy fromphosphorescent emitter transfer to the host molecules and thus assuring the emission ofdevices was all from the phosphorescent emitter. The good electron transport capacity of134OXD with strong electron affinity of1,3,4-oxadiazole ring was achieved, in contrast,maybe due to the relatively poorer conjugation and electron affinity of1,2,4-oxadiazole ring,those host materials containing1,2,4-oxadiazole unit were more prone to transport hole basedon the electron/hole only devices. For the iridium(III)bis[(4,6-difluorophenyl)-pyridinate-N,C2’]picolinate (FIrpic)-based blue phosphorescentorganic light-emitting diodes (OLEDs), the devices based on134OXD as host exhibited thehighest maximum luminance of14994cd/m2, and the highest CEmaxof8.75cd/A. For theiridium(III) tris[2-(p-tolyl)pyridine](Ir(mppy)3)-based green phosphorescent devices, thehighest maximum luminance of9158cd/m2, and the highest CEmaxof12.55cd/A wereachieved for134OXD.
In chapter6, a series of pyridine-containing ETMs were developed as an ETL as well as ahole/exciton block layer for FIrpic-based blue phosphorescent OLEDs. The energy levels ofthe ETMs could be finely tuned by the introduction of pyridine rings in the framework and onthe periphery of the molecules. Significantly reduced operating voltage was achieved withoutcompromising EQE by solely tuning the nitrogen atom orientations of those pyidine rings.Unprecedented low operating voltages of2.61and3.03V were realized at1and100cd/m2,giving ever highest power efficiency (PE) values of65.8and59.7lm/W, respectively. Inaddition, the operating voltages at1and100cd/m2could be further reduced to <2.4and2.70V,respectively, by using a host material with a small singlet-triplet exchange energy (ΔEST), andthe threshold voltage for electroluminescence can even be0.2–0.3V lower than the theoreticalminimum value of the photon energy (hv) divided by electron charge (e). Aside from thereduced operating voltage, a further reduced roll-off in efficiency was also achieved by thecombination of an appropriate host material. The current findings make them as potentialcandidates for high-power consumption applications such as in mobile devices and organiclighting.
In chapter7, a series of triazole and pyridine hybrid molecules were successfullysynthesized by typical Suzuki cross-coupling reactions, and their thermal, photophysical andelectrochemical properties are thoroughly studied. Their HOMO and LUMO energy levels arestrongly dependent on the linkage position and the number of benzene ring. By using thesemolecules as an ETL and a hole/exciton-block layer in green phosphorescent OLEDs, muchbetter electron-injection/transport ability was achieved to give significantly reduced drivingvoltage compared with the widely used ETM of[3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole](TAZ) due to theintroduction of strong electrophilic pyridine rings onto the periphery of the molecules. Thedevice based on TPyTAZm exhibits the highest efficiency with a maximum PE up to73.6lm/W (72.2cd/A,21.8%) due to the matched energy level, high electron transport ability, andthus more balanced carrier recombination. In addition, compared with the device based onTAZ, it shows much higher PE of58.3and42.3lm/W at the practical brightness of100and1000cd/m2due to its good triplet exciton confinement ability and reduced efficiency roll-off.The current findings are beneficial to the design of triazole–based ETMs for furtherimprovement of phosphorescent OLEDs.
In chapter8, a series of water/alcohol-soluble small molecules based on electron-deficientpyridinium salt were successfully designed and synthesized. Their photophysical andelectrochemical properties were thoroughly studied. Due to its good film-forming ability,F8PS was employed as an ETL in polymer solar cells (PSCs). Simultaneous enhancements inopen-circuit voltage (Voc), short circuit current density (Jsc), and fill factor (FF) were achieved,and power conversion efficiency (PCE) was increased from4.32%to6.56%compared to thedevice based on the bare Al cathode. Vocwas significantly improved from0.76V to0.94V,and it is one of the best results reported in literature to date for the PSCs based on the activelayer of poly [N-9’-heptadecanyl-2,7-carbazole-alt-5,5-(4’,7’-di-2-thienyl-2’,1’,3’-benzothiadiazole)](PCDTBT):[6,6]-phenyl-C71-butyric acid methylester(PC71BM). The greatly increased Vocmay be due to the interface dipoles generated by F8PS. Itwas also demonstrated that post treatment of the active layer with ethanol, improvement of the overall device efficiency from the initial4.32%to5.55%compared to the device with the bareAl cathode. Therefore, the improvement in performance after pyridinium salt deposition maybe due to a combination of the effects of ethanol treatment and the presence of the thinpyridinium salt layer. The good water/alcohol solubility, ideal HOMO/LUMO energy levels,excellent electron transfer ability of the hydrophilic pyridinium salt derivatives urges them tobe a promising family of solution-processable ETMs.
引文
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