基于四苯基硅烷的宽禁带半导体材料的设计合成与光电性能研究
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摘要
宽禁带半导体材料通常是指带隙大于3.0eV的材料，这种材料通常具有高能量的吸收与发射(深蓝-紫外光)。由于这类材料具有较高的能量，通常应用于发光、防伪、消毒杀菌、检测、传感等领域。其中最重要一项应用是电致发光领域。由于具有较高的能量，这类材料即可以作为主动发光的材料，发射高能量的光，进而激发蓝、绿、红等低能量的光色；也可以作为母体材料掺杂荧光与磷光染料，作为能量传递的媒介与分散介质，使掺杂的客体材料可以高效率的发光。
目前宽带隙半导体材料面临的关键是如何提高该类材料的载流子注入与传输能力。宽禁带材料本身具有较高的LUMO与较深的HOMO能级，使其载流子注入传输能力较差，限制了其在电致发光中的应用。而改善了注入与传输能力的宽禁带材料又受制于分子内给受体间电荷转移影响而降低带隙，无法应用到高能量的领域。因此本论文立足于寻求解决带宽与载流子注入与迁移矛盾的方法，构筑高性能的宽带系材料，对材料体系热、光、电等性质进行优化，希望在宽禁带材料体系的结构新能关系方面有更深入认识，同时在高性能的材料与器件方面有所突破。
我们通过对文献的调研，筛选出三种优良的构筑宽带材料的中心基团：芴、二苯基醚、四苯基硅烷。通过对中心基团进行给受体的修饰，对其各方面性质进行对比分析。其中二苯基醚分子合成最为简便，芴分子具有最好的热学稳定性，四苯基硅烷具有良好的电子亲和性与形貌稳定性。四苯基硅烷分子具有最优的综合性能，其在磷光掺杂器件中表现优异。这主要是因为：四面体结构打断共轭使其具有超高的带隙宽度(单线态能级在4.0eV左右)；柔性的碳-硅键使分子与客体之间具有良好的相容性；独特的电子结构可以形成dπ-pπ共轭，有效降低LUMO能级，提高电子的亲和性；易于取代使其性质更富多样化。因此在之后的章节中将针对四苯基硅烷基团进行进一步的性质优化。
接下来的一章，我们将承接之前的工作，针对四苯基硅烷电学性质进行优化。我们利用带隙较宽且分别具有给受体能力的咔唑与二苯基磷酰基对四苯基硅烷的载流子迁移能力进行优化，同时我们通过改变咔唑的取代数量与取代方式，调节电子与空穴平衡性，最终发现分子DCzSiPO具有较为优异的性质，其磷光掺杂器件的电流效率与外量子效率分别达到了24.6cd/A与11.2%。为了测试宽带隙材料在电致发光中的应用，我们在空穴与电子传输层中应用了宽禁带材料，制备了传输层与母体材料全为宽禁带材料的掺杂器件。与传统材料体系相比，应用了宽带隙材料的掺杂器件表现优异，最高电流效率与外量子效率分别达到了49.4cd/A与27.5%。在本章工作中我们比较了咔唑取代数量与取代性质的性质差别，最终发现咔唑二聚体为优于咔唑的空穴传输基团。
之后的工作我们进一步通过取代基团改变构筑了蓝色发光四苯基硅烷衍生物。我们将高效发光基团菲并咪唑引入四苯基硅烷，设计了具有高发光效率的材料。同时，利用宽带隙基团咔唑与咔唑二聚体优化菲并咪唑材料的空穴亲和性。最终我们发展了一种电子空穴平衡的材料DCzSiPPIM，其非掺杂器件的外量子效率达到了3.5%，激子利用率达到了26.1%，达到了荧光材料的极限。通过对基本性质表征，我们发现，空穴基团的引入在不改变材料的光学性质的前提下优化了电学性能，这与我们小组之前的工作显示出一致的结果，再一次证明了由于四苯基硅烷的打断作用阻隔了分子内给受体之间的电荷转移作用，可以实现分子光电性能的选择性调节。
在之前的工作中，我们发现对于四苯基硅烷进行指定给受体单元的取代可以实现较宽的带隙与平衡的载流子注入与传输的统一，为了适应商业化的要求我们发展了一种简单有效的方法，使宽禁带材料更适合应用于可大面积加工的溶液制备方法。在载流子平衡方面我们选择了已有的基团，利用咔唑与二苯基磷酰基取代分子；基于对热学性能的优化，我们简单的引入了双重四苯基硅烷中心，加倍四苯基硅烷基团对于分子热学性能的影响，发展了系列可用于溶液加工的材料。通过对基本性质表征，我们发现双重四苯基硅烷中心的分子具有更好的热学与形貌学的稳定性，同时其光物理，电学性质没有变化，我们成功实现了对热学与形貌学性质的选择性调控。相比于单中心的分子，双中心分子在旋涂加工的掺杂器件具有更高的效率。本章的研究工作也进一步说明四苯基硅烷本身不显示电性的中性特质。
Wide-band-gap materials generally possess band gap larger than3.0eV which canabsorb and emit deep blue or ultraviolet (UV) light. With such high energy, thesematerials are usually applied to UV light emitting diodes (LEDs), UV detection, andespecially to organic light emitting diodes (OLEDs). They can either be used asexcitation sources to active light with low energy such as blue, green and red or ashost matrixes for fluorescent and phosphorescent dyes.
Compared with their inorganic counterparts, organic semiconductors have moreadvantages. For example finely adjusted photoelectric properties resulting from easysynthesis and modulation, diversified film forming technics such as vacuumdeposition, solution possessing and flexible display. So the organic materials areconsiderable materials for the future.
Suffered from characteristic wide band gap, organic wide-band-gap materialsusually have high lying LUMO energy and low lying HOMO energy level leading topoor electron and hole injecting and transporting properties. The introduction of donorand acceptor unit to optimize the charge injection and transporting properties creates anew problem reduced bandgap caused by uncontrollable intramolecular chargetransfer. In this thesis, we are searching for excellent wide-band-gap materials systemand mudulating the thermal, morphological, photophysical, electrochemical andelectroluminescent properties. For one hand we develop new materials and fabricatedevices with high efficiency, on the other hand we reveal the natural properties ofthese materials.
In Chapter2three wide-band-gap cores were chosen to verify which one was the best for constructing wide-band-gap materials. Donor and acceptor units wereintroduced in these three cores. Different cores led to different advantages. Thediphenylether cored materials were the most easily to synthesis caused by simplestructures. The fluorene cored compounds possessed the highest thermal stabilityresulting from rigid framework. The tetraphenylsilane cored molecules had the mostexcellent device performances because of favorable electron affinity and stablemorphology. The result revealed the best choice for constructing wide-band-gapmaterials were tetraphenysilane core.
In the next chapter, we optimized the electrical properties according to theprevious work. Wide-band-gap donor carbazole unit and acceptor groupdiphenylphosphrine oxide (PO) were substituted on tetraphenylsilane core. And wealso adjust the numbers and link fashion of carbazole to tune the balance of electronand hole fluxes. Finally we found the combination of carbazole dimer and PO unitwas the best for electroluminescent properties. DCzSiPO based FIrpic doped deviceachieved the highest current efficiency and EQE of24.6cd/A and11.2%respectively.To further test the application of wide-band-gap materials in OLEDs, twosilicon-cored wide bandgap materials were used as electron and hole transportinglayer. Compared to the classic materials wide bandgap materials reached highefficiency of49.4cd/A and27.5%, respectively. The high efficiency indicated theimportance of wide-band-gap materials in OLEDs. Moreover, we found that carbazoledimer unit was better than sole carbazole group as donor unit.
In Chapter3, we endowed tetrphenylsilane blue emitting properties bycombination of phenanthro[9,10-d]imidazole unit which was considered to be highefficient blue emitting group and excellent electron transporting unit. According to thecharacteristics of separation of electrical and optical band-gap, we selectivelymodulating the hole affinity without changing the optical properties ofphenanthro[9,10-d]imidazole substituted silanes by combination of carbazole group.We developed one high efficient molecule named DCzSiPPIM. The undoped devicebase on DCzSiPPIM achieved high EQE of3.5%and high utilization of exitons of26.1%which reached the limit of local fluorescent materials.
In the next chapter, in order to apply in solution-possessing device, we furtheroptimize the thermal and morphological properties. Two tetraphenylsilane cores wereintroduced to construct compounds. According to the previous work we still usedcarbazole and PO unit to modulate the electrical properties. One extra hole unit wereadded to overcome the problem of lacking of hole flux in solution-possessing device.The introduction of double tetraphenylsilane centers greatly improved the thermal andmorphological properties without changing the optical and electrical properties. Thedoping device based on DCS2PO host materials achieved high current efficiency of26.5cd/A which was two times higher than that of device based on its singlecounterpart. All the result revealed the neutral property of silane.
目前宽带隙半导体材料面临的关键是如何提高该类材料的载流子注入与传输能力。宽禁带材料本身具有较高的LUMO与较深的HOMO能级，使其载流子注入传输能力较差，限制了其在电致发光中的应用。而改善了注入与传输能力的宽禁带材料又受制于分子内给受体间电荷转移影响而降低带隙，无法应用到高能量的领域。因此本论文立足于寻求解决带宽与载流子注入与迁移矛盾的方法，构筑高性能的宽带系材料，对材料体系热、光、电等性质进行优化，希望在宽禁带材料体系的结构新能关系方面有更深入认识，同时在高性能的材料与器件方面有所突破。
我们通过对文献的调研，筛选出三种优良的构筑宽带材料的中心基团：芴、二苯基醚、四苯基硅烷。通过对中心基团进行给受体的修饰，对其各方面性质进行对比分析。其中二苯基醚分子合成最为简便，芴分子具有最好的热学稳定性，四苯基硅烷具有良好的电子亲和性与形貌稳定性。四苯基硅烷分子具有最优的综合性能，其在磷光掺杂器件中表现优异。这主要是因为：四面体结构打断共轭使其具有超高的带隙宽度(单线态能级在4.0eV左右)；柔性的碳-硅键使分子与客体之间具有良好的相容性；独特的电子结构可以形成dπ-pπ共轭，有效降低LUMO能级，提高电子的亲和性；易于取代使其性质更富多样化。因此在之后的章节中将针对四苯基硅烷基团进行进一步的性质优化。
接下来的一章，我们将承接之前的工作，针对四苯基硅烷电学性质进行优化。我们利用带隙较宽且分别具有给受体能力的咔唑与二苯基磷酰基对四苯基硅烷的载流子迁移能力进行优化，同时我们通过改变咔唑的取代数量与取代方式，调节电子与空穴平衡性，最终发现分子DCzSiPO具有较为优异的性质，其磷光掺杂器件的电流效率与外量子效率分别达到了24.6cd/A与11.2%。为了测试宽带隙材料在电致发光中的应用，我们在空穴与电子传输层中应用了宽禁带材料，制备了传输层与母体材料全为宽禁带材料的掺杂器件。与传统材料体系相比，应用了宽带隙材料的掺杂器件表现优异，最高电流效率与外量子效率分别达到了49.4cd/A与27.5%。在本章工作中我们比较了咔唑取代数量与取代性质的性质差别，最终发现咔唑二聚体为优于咔唑的空穴传输基团。
之后的工作我们进一步通过取代基团改变构筑了蓝色发光四苯基硅烷衍生物。我们将高效发光基团菲并咪唑引入四苯基硅烷，设计了具有高发光效率的材料。同时，利用宽带隙基团咔唑与咔唑二聚体优化菲并咪唑材料的空穴亲和性。最终我们发展了一种电子空穴平衡的材料DCzSiPPIM，其非掺杂器件的外量子效率达到了3.5%，激子利用率达到了26.1%，达到了荧光材料的极限。通过对基本性质表征，我们发现，空穴基团的引入在不改变材料的光学性质的前提下优化了电学性能，这与我们小组之前的工作显示出一致的结果，再一次证明了由于四苯基硅烷的打断作用阻隔了分子内给受体之间的电荷转移作用，可以实现分子光电性能的选择性调节。
在之前的工作中，我们发现对于四苯基硅烷进行指定给受体单元的取代可以实现较宽的带隙与平衡的载流子注入与传输的统一，为了适应商业化的要求我们发展了一种简单有效的方法，使宽禁带材料更适合应用于可大面积加工的溶液制备方法。在载流子平衡方面我们选择了已有的基团，利用咔唑与二苯基磷酰基取代分子；基于对热学性能的优化，我们简单的引入了双重四苯基硅烷中心，加倍四苯基硅烷基团对于分子热学性能的影响，发展了系列可用于溶液加工的材料。通过对基本性质表征，我们发现双重四苯基硅烷中心的分子具有更好的热学与形貌学的稳定性，同时其光物理，电学性质没有变化，我们成功实现了对热学与形貌学性质的选择性调控。相比于单中心的分子，双中心分子在旋涂加工的掺杂器件具有更高的效率。本章的研究工作也进一步说明四苯基硅烷本身不显示电性的中性特质。
Wide-band-gap materials generally possess band gap larger than3.0eV which canabsorb and emit deep blue or ultraviolet (UV) light. With such high energy, thesematerials are usually applied to UV light emitting diodes (LEDs), UV detection, andespecially to organic light emitting diodes (OLEDs). They can either be used asexcitation sources to active light with low energy such as blue, green and red or ashost matrixes for fluorescent and phosphorescent dyes.
Compared with their inorganic counterparts, organic semiconductors have moreadvantages. For example finely adjusted photoelectric properties resulting from easysynthesis and modulation, diversified film forming technics such as vacuumdeposition, solution possessing and flexible display. So the organic materials areconsiderable materials for the future.
Suffered from characteristic wide band gap, organic wide-band-gap materialsusually have high lying LUMO energy and low lying HOMO energy level leading topoor electron and hole injecting and transporting properties. The introduction of donorand acceptor unit to optimize the charge injection and transporting properties creates anew problem reduced bandgap caused by uncontrollable intramolecular chargetransfer. In this thesis, we are searching for excellent wide-band-gap materials systemand mudulating the thermal, morphological, photophysical, electrochemical andelectroluminescent properties. For one hand we develop new materials and fabricatedevices with high efficiency, on the other hand we reveal the natural properties ofthese materials.
In Chapter2three wide-band-gap cores were chosen to verify which one was the best for constructing wide-band-gap materials. Donor and acceptor units wereintroduced in these three cores. Different cores led to different advantages. Thediphenylether cored materials were the most easily to synthesis caused by simplestructures. The fluorene cored compounds possessed the highest thermal stabilityresulting from rigid framework. The tetraphenylsilane cored molecules had the mostexcellent device performances because of favorable electron affinity and stablemorphology. The result revealed the best choice for constructing wide-band-gapmaterials were tetraphenysilane core.
In the next chapter, we optimized the electrical properties according to theprevious work. Wide-band-gap donor carbazole unit and acceptor groupdiphenylphosphrine oxide (PO) were substituted on tetraphenylsilane core. And wealso adjust the numbers and link fashion of carbazole to tune the balance of electronand hole fluxes. Finally we found the combination of carbazole dimer and PO unitwas the best for electroluminescent properties. DCzSiPO based FIrpic doped deviceachieved the highest current efficiency and EQE of24.6cd/A and11.2%respectively.To further test the application of wide-band-gap materials in OLEDs, twosilicon-cored wide bandgap materials were used as electron and hole transportinglayer. Compared to the classic materials wide bandgap materials reached highefficiency of49.4cd/A and27.5%, respectively. The high efficiency indicated theimportance of wide-band-gap materials in OLEDs. Moreover, we found that carbazoledimer unit was better than sole carbazole group as donor unit.
In Chapter3, we endowed tetrphenylsilane blue emitting properties bycombination of phenanthro[9,10-d]imidazole unit which was considered to be highefficient blue emitting group and excellent electron transporting unit. According to thecharacteristics of separation of electrical and optical band-gap, we selectivelymodulating the hole affinity without changing the optical properties ofphenanthro[9,10-d]imidazole substituted silanes by combination of carbazole group.We developed one high efficient molecule named DCzSiPPIM. The undoped devicebase on DCzSiPPIM achieved high EQE of3.5%and high utilization of exitons of26.1%which reached the limit of local fluorescent materials.
In the next chapter, in order to apply in solution-possessing device, we furtheroptimize the thermal and morphological properties. Two tetraphenylsilane cores wereintroduced to construct compounds. According to the previous work we still usedcarbazole and PO unit to modulate the electrical properties. One extra hole unit wereadded to overcome the problem of lacking of hole flux in solution-possessing device.The introduction of double tetraphenylsilane centers greatly improved the thermal andmorphological properties without changing the optical and electrical properties. Thedoping device based on DCS2PO host materials achieved high current efficiency of26.5cd/A which was two times higher than that of device based on its singlecounterpart. All the result revealed the neutral property of silane.
引文
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