多羟基修饰的有机小分子空穴传输材料的合成与表征
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摘要
随着有机电致发光二极管(Organic light-emitting diodes, OLEDs)的发展，研究者们的注意力开始向低成本、大面积、易加工等方面转移。为了克服热蒸镀法制备OLED过程中面对的各种问题，溶液加工OLED器件开始引起人们重视。其核心是发光层由溶液法制备。由此，需要克服，在溶液加工过程中，发光层与相邻功能层间界面互溶的现象。
本论文报道了一系列新型多羟基修饰的小分子空穴传输材料，探索了在弱极性、极性醇类溶剂中的溶解性与分子结构之间的关系，以及在“发光层经由溶液加工成膜”的正装OLED器件中的应用。具体内容如下：
1.设计合成了三种多羟基化合物2OH-1、2OH-2和6OH。其中2OH-1分子具有两个羟基，但材料在极性溶剂，如甲醇，以及弱极性溶剂中，如甲苯，溶解度都较好，譬如在甲醇与甲苯中溶解度都超过20mg/mL。而2OH-2，在上述溶剂中溶解度都大幅度降低，如其在甲醇与甲苯中溶解度都小于1mg/mL。随后合成了6OH，相对于2OH-2增加羟基数目至6个，但在醇类溶剂中溶解性依然没有提高。
2.在上述基础上，改变分子设计策略。在分子的外围侧基上引入羟基，设计合成了10OH，得到的化合物在甲醇、乙醇或异丙醇中的溶解度均大于50mg/mL，而在甲苯、对二甲苯或氯苯中溶解度小于0.1mg/mL。经过AFM以及吸收光谱测试发现，采用弱极性溶剂，如甲苯等洗涤不会其表面形貌或厚度产生明显影响。通过单空穴器件ITO/MoO_3(10nm)/10OH (130nm)/MoO_3(10nm)/Al (100nm)测得其空穴迁移率为4.6×10~(-6)cm~2V-1s~(-1)。而器件ITO/10OH (30nm)/P-PPV(80nm)/CsF(1.5nm)/Al(200nm)，启亮电压仅有2.6V，最大电流效率为19.8cdA-1。
3.为了减少空穴传输材料在可见光附近的吸收，设计化合物4OH与5OH。虽然二者结构类似，但溶解性相差很大。4OH溶解性与10OH类似；而5OH则不溶于醇类及弱极性溶剂。4OH的空穴迁移率可达1.5×10~(-7)cm~2V-1s~(-1)。
Organic light-emitting diodes (OLEDs) based on solution processing have beenreceiving increasing attention due to the possibility to afford low-cost, large-area and flexibledevices. Nevertheless, solution processing presents demanding challenges such as interlayermixing of adjacent functional layers. In this context, we report the synthesis of a new class ofmultihydroxylated small-molecule hole-transport compounds in an attempt to obtainalcohol-processable hole-transport materials that are compatible to the emitting layer, whichgenerally consists of hydrophobic material(s). The molecular structure propertiesrelationships such as on solubility in alcohol and weakly-polar solvents and hole-transportmobility are discussed. It is noteworthy that a compound with high solubility in alcoholsolvents whilst insoluble in weakly polar solvents was used as a hole-transport layer inbottom-anode OLEDs that consisted of a solution-processed thin polymer emitting layer,leading to promising device performance. The details as follows:
1. Three multihydroxylated hole-transport molecules,2OH-1,2OH-2and6OH, havebeen synthesized.2OH-1is soluble in both alcohol and weakly polar solvents such as tolueneand xylenes, with a solubility of at least20mg/mL. Further attaching four triphenylaminogroups to the endgroups of2OH-1,2OH-2is obtained. However, the resulting solubility inalcohol and weakly polar solvents is severely reduced, less than ca.1mg/mL. The synthesisof6OH fails to improve solubility, especially in alcohol solvents.
2. On the basis of the above work,10OH has been designed and synthesized with10hydroxyl groups in a molecule.10OH shows a high solubility in polar solvents whilst barelysoluble in weakly polar solvents. For instance, more than50mg of10OH facilely dissolves in1mL methanol, ethanol or2-propanol at room temperature, while0.1mg of the compound isinsoluble in1mL toluene, p-xylene, and chlorobenzene. Furthermore, this multihydroxylatedcompound is capable of affording uniform amorphous, smooth and transparent films,spin-cast from2-propanol with a high Tgof190°C. The resistance to weakly polar solventsuch as toluene of the resulting film is confirmed by AFM and UV-Vis absorption experiments.Hole mobility of10OH is4.6×10-6cm2V-1s~(-1)measured by fabricating single carrierhole-only device ITO/MoO_3(10nm)/10OH (130nm)/MoO_3(10nm)/Al (100nm).10OH isutilized as a hole-transport layer in OLED [ITO/10OH (30nm)/P-PPV (80nm)/CsF (1.5nm)/Al (200nm)] exhibited a maximal luminous efficiency (LEmax) as high as19.8cd A-1anda low turn-on voltage of2.6V.
3. Subsequently, in order to reduce visible light absorption of the above10OHhole-transport compound,4OH and5OH have been synthesized. While4OH has a highsolubility in alcohol solvents,5OH is almost insoluble. Hole mobility of4OH, revealed by SCLC at low voltages, is1.5×10~(-7)cm~2V-1s~(-1).
本论文报道了一系列新型多羟基修饰的小分子空穴传输材料，探索了在弱极性、极性醇类溶剂中的溶解性与分子结构之间的关系，以及在“发光层经由溶液加工成膜”的正装OLED器件中的应用。具体内容如下：
1.设计合成了三种多羟基化合物2OH-1、2OH-2和6OH。其中2OH-1分子具有两个羟基，但材料在极性溶剂，如甲醇，以及弱极性溶剂中，如甲苯，溶解度都较好，譬如在甲醇与甲苯中溶解度都超过20mg/mL。而2OH-2，在上述溶剂中溶解度都大幅度降低，如其在甲醇与甲苯中溶解度都小于1mg/mL。随后合成了6OH，相对于2OH-2增加羟基数目至6个，但在醇类溶剂中溶解性依然没有提高。
2.在上述基础上，改变分子设计策略。在分子的外围侧基上引入羟基，设计合成了10OH，得到的化合物在甲醇、乙醇或异丙醇中的溶解度均大于50mg/mL，而在甲苯、对二甲苯或氯苯中溶解度小于0.1mg/mL。经过AFM以及吸收光谱测试发现，采用弱极性溶剂，如甲苯等洗涤不会其表面形貌或厚度产生明显影响。通过单空穴器件ITO/MoO_3(10nm)/10OH (130nm)/MoO_3(10nm)/Al (100nm)测得其空穴迁移率为4.6×10~(-6)cm~2V-1s~(-1)。而器件ITO/10OH (30nm)/P-PPV(80nm)/CsF(1.5nm)/Al(200nm)，启亮电压仅有2.6V，最大电流效率为19.8cdA-1。
3.为了减少空穴传输材料在可见光附近的吸收，设计化合物4OH与5OH。虽然二者结构类似，但溶解性相差很大。4OH溶解性与10OH类似；而5OH则不溶于醇类及弱极性溶剂。4OH的空穴迁移率可达1.5×10~(-7)cm~2V-1s~(-1)。
Organic light-emitting diodes (OLEDs) based on solution processing have beenreceiving increasing attention due to the possibility to afford low-cost, large-area and flexibledevices. Nevertheless, solution processing presents demanding challenges such as interlayermixing of adjacent functional layers. In this context, we report the synthesis of a new class ofmultihydroxylated small-molecule hole-transport compounds in an attempt to obtainalcohol-processable hole-transport materials that are compatible to the emitting layer, whichgenerally consists of hydrophobic material(s). The molecular structure propertiesrelationships such as on solubility in alcohol and weakly-polar solvents and hole-transportmobility are discussed. It is noteworthy that a compound with high solubility in alcoholsolvents whilst insoluble in weakly polar solvents was used as a hole-transport layer inbottom-anode OLEDs that consisted of a solution-processed thin polymer emitting layer,leading to promising device performance. The details as follows:
1. Three multihydroxylated hole-transport molecules,2OH-1,2OH-2and6OH, havebeen synthesized.2OH-1is soluble in both alcohol and weakly polar solvents such as tolueneand xylenes, with a solubility of at least20mg/mL. Further attaching four triphenylaminogroups to the endgroups of2OH-1,2OH-2is obtained. However, the resulting solubility inalcohol and weakly polar solvents is severely reduced, less than ca.1mg/mL. The synthesisof6OH fails to improve solubility, especially in alcohol solvents.
2. On the basis of the above work,10OH has been designed and synthesized with10hydroxyl groups in a molecule.10OH shows a high solubility in polar solvents whilst barelysoluble in weakly polar solvents. For instance, more than50mg of10OH facilely dissolves in1mL methanol, ethanol or2-propanol at room temperature, while0.1mg of the compound isinsoluble in1mL toluene, p-xylene, and chlorobenzene. Furthermore, this multihydroxylatedcompound is capable of affording uniform amorphous, smooth and transparent films,spin-cast from2-propanol with a high Tgof190°C. The resistance to weakly polar solventsuch as toluene of the resulting film is confirmed by AFM and UV-Vis absorption experiments.Hole mobility of10OH is4.6×10-6cm2V-1s~(-1)measured by fabricating single carrierhole-only device ITO/MoO_3(10nm)/10OH (130nm)/MoO_3(10nm)/Al (100nm).10OH isutilized as a hole-transport layer in OLED [ITO/10OH (30nm)/P-PPV (80nm)/CsF (1.5nm)/Al (200nm)] exhibited a maximal luminous efficiency (LEmax) as high as19.8cd A-1anda low turn-on voltage of2.6V.
3. Subsequently, in order to reduce visible light absorption of the above10OHhole-transport compound,4OH and5OH have been synthesized. While4OH has a highsolubility in alcohol solvents,5OH is almost insoluble. Hole mobility of4OH, revealed by SCLC at low voltages, is1.5×10~(-7)cm~2V-1s~(-1).
引文
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