有机蓝色荧光材料和磷光主体材料的合成及电致发光性质研究
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摘要
本论文设计并合成了一系列有机小分子类、聚合物类蓝色荧光材料,以及具有不同特点的磷光主体材料,详细地研究了它们的电致发光性能。所合成的材料类型和具体工作如下：
(1)聚芴衍生物类蓝色荧光材料：将具有不同吸电子能力的三氟甲基苯基和二氟苯基通过Suzuki缩聚反应引入到聚芴主链上,同时调节了它们在主链上的比例,合成了两个系列聚芴衍生物蓝色荧光材料。与聚芴相比,所得聚合物不仅具有高的荧光量子效率,而且在光谱的色纯度和稳定性方面得到了较大的改善。以聚合物为发光层,通过溶液旋涂方法制备的有机电致发光器件均表现出纯正的蓝光发射。其中基于PF-33F的器件性能明显优于聚芴,最大外量子效率和色坐标分别为1.14%和(0.16,0.13)。
(2)含有芴或咔唑中心的小分子蓝色荧光材料：通过Suzuki偶联反应,分别以芴、联芴或咔唑为分子中心,在其2,7位引入9-(2-萘基)蒽,设计并合成了两个系列小分子蓝色荧光材料。这些化合物均具有良好的热稳定性、形态稳定性以及高的荧光量子效率。将它们作为发光层,利用真空蒸镀技术制备的非掺杂型器件均获得深蓝光,色坐标非常接近于标准蓝光(0.14,0.08)。其中,基于NAECz的器件性能最优,最大电流效率和外量子效率分别达到了6.91cdA-1和7.60%,是目前报道的色坐标y<0.10的非掺杂型深蓝色荧光器件中的最高效率。此外,将NAECz与橙色荧光材料DCJTB组合作为发光层,制备的二元白光器件最大亮度可以达到36250cdm-2,最大电流效率和色坐标分别为17.75cdA-1和(0.35,0.36),也是目前文献报道的基于荧光材料的二元白光器件中的最高效率。
(3)双极性小分子磷光主体材料：在CBP咔唑环的3-位碳上引入强吸电子性的氰基,合成了一种新型的CBP衍生物CBP-CN。单电子器件的电流-电压性质研究证实了CBP-CN具有既传输空穴又传输电子的双极性特征。与CBP相比,CBP-CN具有更高的Tg值(162℃)和更低的HOMO和LUMO能级,但是其能隙值和三线态能级(2.69eV)却没有发生明显改变。将其作为主体材料制备了绿色和红色电致磷光器件,最大电流效率分别为80.61cd A-1(23.13%)和10.67cd A-1(15.54%),与基于CBP的器件相比,分别提高了25%和33%。其中,绿光器件的效率接近于目前文献报道的磷光器件中的最好数据(92.2cd A-1和26.8%)。
(4)树枝状磷光主体材料：以联苯为核心,通过Ullmann偶联反应在其两端引入具有空穴传输功能的不同代数的低聚咔唑类树枝,合成了一系列树枝状分子：G1、G2和G3。与传统的小分子磷光主体材料CBP相比,所得化合物具有类似的三线态能级(2.60-2.62eV),但其树枝状的结构使这些材料具有良好的无定型态的特点,玻璃化转变温度最高可达到376℃,且适合溶液加工方法制备器件。与常用的磷光主体材料PVK相比,这些树枝状分子具有更高的HOMO能级(-5.51eV到-5.37eV)。以G2为主体,铱配合物为客体,制备的绿色和橙红色电致磷光器件最大效率分别为38.71cd A-1和32.22cd A-1,明显优于基于PVK的器件,是目前报道的通过溶液加工制备磷光器件中的较好数据。
(5)可溶液加工的小分子磷光主体材料：以三杜烯硼烷为核心,通过Suzuki偶联在其三个对位引入芴或联芴,合成了两种小分子磷光主体材料：DBF1和DBF2。这些材料具有良好的溶解性和热稳定性。其中,DBF1具有较高的三线态能级,将其作为主体,通过溶液旋涂方法制备的绿色电致磷光器件表现出较好的性能,器件的最大效率分别为36.77cd A-1、23.09lm W-1和10.81％。
A series of blue organic fluorescent materials and phosphorescent host materials were designed and synthesized. The electroluminescent properties of these materials were studied. The material types and their specific works are as follows:
(1) Polyfluorene (PF)-type of blue fluorescent materials:A group of fluorene-based copolymers were synthesized by introduction of different content ratios of electron-withdrawing groups, such as trifiuoromethylphenylene or p-difluorophenylene, to the polymer backbone through Suzuki polycondensation reactions. In contrast to the pristine polyfluorene, these copolymers possess increased fluorescent quantum yields and improved spectra purity and stability of the blue fluorescence. Organic light-emitting diodes were fabricated by spin coating method using them as emitting layer and pure blue electroluminescence was obtained. A maximum external quantum efficiency of1.14%and the CIE (0.16,0.13) were achieved for PF-33F device, which far exceed those of the control device base on the parent polyfluorene.
(2) Fluroene-or carbazole-cored small molecular blue fluorescent materials:By introducing9-naphthylanthracene endcaps into oligofluorene or carbazole core through Suzuki coupling reactions, two series of blue fluorescent molecules have been designed and synthesized. These materials exhibit excellent thermal and amorphous stabilities, and high fluorescence quantum yield. Vacumn deposited organic light-emitting devices (OLEDs) using these materials as non-doped emitter exhibited bright deep blue electroluminescence, and the CIE coordinates are quite close to the National Television System Committee (NTSC) standard blue of (0.14,0.08). The devices based on NAECz exhibit excellent device performances with maximum r efficiencies of6.91cd A"1and7.60%, which are among the best performance ever reported for deep-blue OLEDs with a low CIE coordinate y<0.1. In addition, the white OLEDs using NAECz as blue host and a traditional fluorophore DCJTB as yellow dopant realized a high luminance of36250cd m"2and an efficiency of17.75cd A-with an almost standard white light coordinates of (0.35,0.36), which is also among the best results ever reported for two-emitting-component white OLEDs based on fluorescent materials.
(3) Small molecular bipolar phosphorescent host material:We report the synthesis and properties of one novel CBP derivative, CBP-CN, with two cyano groups (CN) at the3-sites of both carbazole rings. The strong electron-withdrawing CN was introduced with expectation to promote electron-injecting/-transporting abilities and to achieve bipolar feature for CBP-CN. In comparison with the parent CBP, CBP-CN possesses lowered HOMO and LUMO levels and dramatically increased Tg(162℃), but unaltered HOMO-LUMO band gap and triplet energy (2.69eV). Green and red PhOLEDs were fabricated with CBP-CN as hosts for traditional iridium phosphors. The maximum luminance efficiency (ηL) of80.61cd A-1(23.13%) was achieved for green PhOLED, and10.67cd A-1(15.54%) for red one, respectively, which represent a efficiency increase by25-33%than those of the best devices with CBP host. The efficiencies of the present green PhOLEDs are even close to the best data for phosphorescent OLEDs reported so far (92.2cd A-1and26.8%).
(4) Dendritic phosphorescent host materials:A group of dendrimers with oligo-carbazole dendrons appended at4,4'-positions of biphenyl core, namely G1, G2and G3, were synthesized by Ullmann coupling reaction. In comparison with the traditional small molecular phosphorescent host CBP, the dendritic conformation affords these materials with extra merits of being inherent amorphous with extremely high glass transition temperatures of e.g.376℃and being suitable for solution-processing techniques to make devices, in addition to the similarly high triplet energies (2.60-2.62eV). In comparison with the widely-used phosphorescent polymer host polyvinylcarbazole (PVK), these dendrimers possess much higher HOMO levels (-5.51eV to-5.37eV). These dendrimers were used as host materials for iridium phosphors to fabricate OLEDs by spin coating method and excellent performance were achieved. The green and orange PHOLED containing G2host exhibited high luminance efficiencies of38.71cd A-1and32.22cd A-1, respectively, which far exceed those of the control device with PVK host and are among the best results for solution-processed PHOLEDs reported so far.
(5) Solution-processible small molecular phosphorescent host materials:A group of small molecular phosphorescent hosts based on a tridurylboranes core and oligofluorene endcaps, namely DBF1DBF2, were synthesized via Suzuki coupling reactions. These materials show good solubility and excellent thermal stability. DBF1has high triplet energy. Green phosphorescent OLEDs were fabricated by partially solution-processing technique with DBF1as host and exhibited good device performances with high efficiencies of36.77cd A-1,23.09lm W-1and10.81%.
(1)聚芴衍生物类蓝色荧光材料：将具有不同吸电子能力的三氟甲基苯基和二氟苯基通过Suzuki缩聚反应引入到聚芴主链上,同时调节了它们在主链上的比例,合成了两个系列聚芴衍生物蓝色荧光材料。与聚芴相比,所得聚合物不仅具有高的荧光量子效率,而且在光谱的色纯度和稳定性方面得到了较大的改善。以聚合物为发光层,通过溶液旋涂方法制备的有机电致发光器件均表现出纯正的蓝光发射。其中基于PF-33F的器件性能明显优于聚芴,最大外量子效率和色坐标分别为1.14%和(0.16,0.13)。
(2)含有芴或咔唑中心的小分子蓝色荧光材料：通过Suzuki偶联反应,分别以芴、联芴或咔唑为分子中心,在其2,7位引入9-(2-萘基)蒽,设计并合成了两个系列小分子蓝色荧光材料。这些化合物均具有良好的热稳定性、形态稳定性以及高的荧光量子效率。将它们作为发光层,利用真空蒸镀技术制备的非掺杂型器件均获得深蓝光,色坐标非常接近于标准蓝光(0.14,0.08)。其中,基于NAECz的器件性能最优,最大电流效率和外量子效率分别达到了6.91cdA-1和7.60%,是目前报道的色坐标y<0.10的非掺杂型深蓝色荧光器件中的最高效率。此外,将NAECz与橙色荧光材料DCJTB组合作为发光层,制备的二元白光器件最大亮度可以达到36250cdm-2,最大电流效率和色坐标分别为17.75cdA-1和(0.35,0.36),也是目前文献报道的基于荧光材料的二元白光器件中的最高效率。
(3)双极性小分子磷光主体材料：在CBP咔唑环的3-位碳上引入强吸电子性的氰基,合成了一种新型的CBP衍生物CBP-CN。单电子器件的电流-电压性质研究证实了CBP-CN具有既传输空穴又传输电子的双极性特征。与CBP相比,CBP-CN具有更高的Tg值(162℃)和更低的HOMO和LUMO能级,但是其能隙值和三线态能级(2.69eV)却没有发生明显改变。将其作为主体材料制备了绿色和红色电致磷光器件,最大电流效率分别为80.61cd A-1(23.13%)和10.67cd A-1(15.54%),与基于CBP的器件相比,分别提高了25%和33%。其中,绿光器件的效率接近于目前文献报道的磷光器件中的最好数据(92.2cd A-1和26.8%)。
(4)树枝状磷光主体材料：以联苯为核心,通过Ullmann偶联反应在其两端引入具有空穴传输功能的不同代数的低聚咔唑类树枝,合成了一系列树枝状分子：G1、G2和G3。与传统的小分子磷光主体材料CBP相比,所得化合物具有类似的三线态能级(2.60-2.62eV),但其树枝状的结构使这些材料具有良好的无定型态的特点,玻璃化转变温度最高可达到376℃,且适合溶液加工方法制备器件。与常用的磷光主体材料PVK相比,这些树枝状分子具有更高的HOMO能级(-5.51eV到-5.37eV)。以G2为主体,铱配合物为客体,制备的绿色和橙红色电致磷光器件最大效率分别为38.71cd A-1和32.22cd A-1,明显优于基于PVK的器件,是目前报道的通过溶液加工制备磷光器件中的较好数据。
(5)可溶液加工的小分子磷光主体材料：以三杜烯硼烷为核心,通过Suzuki偶联在其三个对位引入芴或联芴,合成了两种小分子磷光主体材料：DBF1和DBF2。这些材料具有良好的溶解性和热稳定性。其中,DBF1具有较高的三线态能级,将其作为主体,通过溶液旋涂方法制备的绿色电致磷光器件表现出较好的性能,器件的最大效率分别为36.77cd A-1、23.09lm W-1和10.81％。
A series of blue organic fluorescent materials and phosphorescent host materials were designed and synthesized. The electroluminescent properties of these materials were studied. The material types and their specific works are as follows:
(1) Polyfluorene (PF)-type of blue fluorescent materials:A group of fluorene-based copolymers were synthesized by introduction of different content ratios of electron-withdrawing groups, such as trifiuoromethylphenylene or p-difluorophenylene, to the polymer backbone through Suzuki polycondensation reactions. In contrast to the pristine polyfluorene, these copolymers possess increased fluorescent quantum yields and improved spectra purity and stability of the blue fluorescence. Organic light-emitting diodes were fabricated by spin coating method using them as emitting layer and pure blue electroluminescence was obtained. A maximum external quantum efficiency of1.14%and the CIE (0.16,0.13) were achieved for PF-33F device, which far exceed those of the control device base on the parent polyfluorene.
(2) Fluroene-or carbazole-cored small molecular blue fluorescent materials:By introducing9-naphthylanthracene endcaps into oligofluorene or carbazole core through Suzuki coupling reactions, two series of blue fluorescent molecules have been designed and synthesized. These materials exhibit excellent thermal and amorphous stabilities, and high fluorescence quantum yield. Vacumn deposited organic light-emitting devices (OLEDs) using these materials as non-doped emitter exhibited bright deep blue electroluminescence, and the CIE coordinates are quite close to the National Television System Committee (NTSC) standard blue of (0.14,0.08). The devices based on NAECz exhibit excellent device performances with maximum r efficiencies of6.91cd A"1and7.60%, which are among the best performance ever reported for deep-blue OLEDs with a low CIE coordinate y<0.1. In addition, the white OLEDs using NAECz as blue host and a traditional fluorophore DCJTB as yellow dopant realized a high luminance of36250cd m"2and an efficiency of17.75cd A-with an almost standard white light coordinates of (0.35,0.36), which is also among the best results ever reported for two-emitting-component white OLEDs based on fluorescent materials.
(3) Small molecular bipolar phosphorescent host material:We report the synthesis and properties of one novel CBP derivative, CBP-CN, with two cyano groups (CN) at the3-sites of both carbazole rings. The strong electron-withdrawing CN was introduced with expectation to promote electron-injecting/-transporting abilities and to achieve bipolar feature for CBP-CN. In comparison with the parent CBP, CBP-CN possesses lowered HOMO and LUMO levels and dramatically increased Tg(162℃), but unaltered HOMO-LUMO band gap and triplet energy (2.69eV). Green and red PhOLEDs were fabricated with CBP-CN as hosts for traditional iridium phosphors. The maximum luminance efficiency (ηL) of80.61cd A-1(23.13%) was achieved for green PhOLED, and10.67cd A-1(15.54%) for red one, respectively, which represent a efficiency increase by25-33%than those of the best devices with CBP host. The efficiencies of the present green PhOLEDs are even close to the best data for phosphorescent OLEDs reported so far (92.2cd A-1and26.8%).
(4) Dendritic phosphorescent host materials:A group of dendrimers with oligo-carbazole dendrons appended at4,4'-positions of biphenyl core, namely G1, G2and G3, were synthesized by Ullmann coupling reaction. In comparison with the traditional small molecular phosphorescent host CBP, the dendritic conformation affords these materials with extra merits of being inherent amorphous with extremely high glass transition temperatures of e.g.376℃and being suitable for solution-processing techniques to make devices, in addition to the similarly high triplet energies (2.60-2.62eV). In comparison with the widely-used phosphorescent polymer host polyvinylcarbazole (PVK), these dendrimers possess much higher HOMO levels (-5.51eV to-5.37eV). These dendrimers were used as host materials for iridium phosphors to fabricate OLEDs by spin coating method and excellent performance were achieved. The green and orange PHOLED containing G2host exhibited high luminance efficiencies of38.71cd A-1and32.22cd A-1, respectively, which far exceed those of the control device with PVK host and are among the best results for solution-processed PHOLEDs reported so far.
(5) Solution-processible small molecular phosphorescent host materials:A group of small molecular phosphorescent hosts based on a tridurylboranes core and oligofluorene endcaps, namely DBF1DBF2, were synthesized via Suzuki coupling reactions. These materials show good solubility and excellent thermal stability. DBF1has high triplet energy. Green phosphorescent OLEDs were fabricated by partially solution-processing technique with DBF1as host and exhibited good device performances with high efficiencies of36.77cd A-1,23.09lm W-1and10.81%.
引文
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