基于三芳胺类聚集诱导发光材料的合成和双光子性能研究
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摘要
具有聚集诱导发光效应和大的双光子吸收截面值的有机光电功能材料在生物光子领域具有潜在的应用前景。本论文主要设计合成了三个系列基于三芳胺类的具有聚集诱导发光效应和双光子性能的有机光电功能材料,研究了它们在双光子吸收、荧光和电致发光中的应用性能。
本论文的主要内容包括以下几个方面：
第一章综述了具有聚集诱导发光效应、双光子效应的有机光电功能材料的研究进展,并在此基础上提出了本文的设计思路和研究内容。
第二章设计合成了一类基于三苯基胺的吡咯并吡咯二酮(DPP)类衍生物,研究了该类化合物的聚集诱导发光效应和双光子性能。化合物DPP-Ⅰ和DPP-Ⅱ具有聚集诱导发光的特征,而化合物DPP-Ⅲ则表现出聚集诱导发光增强效应。三个化合物分别采用了D-π-A-π-A,D-兀-A-π-A和D-π-A-π-D(D代表给体,A代表受体)的分子结构。在80飞秒、800 nm激光的激发条件下,三个化合物的双光子吸收截面值分别为188 GM,275 GM和447 GM,其中采用对称分子结构的化合物DPP-Ⅲ具有较高的双光子吸收截面值。
第三章设计合成了一类具有聚集诱导发光效应基于星射状三芳胺和氰基的四极分子双光子材料(CNDPASB(a-c)),为了进行对比,我们也合成了没有氰基基团星射状三芳胺的化合物(DPASB(a-c))。在80飞秒、800 nm激光的激发条件下,化合物CNDPASB(a-c)的双光子吸收截面值分别为1016 GM,1484 GM和814 GM,化合物DPASB(a-c)的双光子吸收截面值分别为540 GM,259 GM和34 GM。另外,化合物CNDPASB(a-c)在溶液中荧光强度接近于零,在聚集态时则发出强烈的荧光,且荧光颜色分别呈现出红色、橙色和黄色,表现出聚集诱导发光效应,而化合物DPASB(a-c)却表现出聚集猝灭现象。将具有聚集发光性能的CNDPASB-a和CNDPASB-c制成有机电致发光二极管,CNDPASB-c器件展现出很强的深黄色荧光且具有很好光色稳定性,最大发光强度达858cd/m2。CNDPASB-a和CNDPASB-c器件的电流效率分别为0.67和0.83 cd/A,两者的最大外部量子效率分别为0.77%和0.33%。
第四章设计合成了以星射状三芳胺为封边给体,三苯胺为核的化合物(TSASB-b),测试了化合物的聚集诱导发光效应和双光子性能。在80飞秒、800 nm激光的激发条件下,化合物TSASB-b双光子吸收截面值为129 GM。化合物TSASB-b在一般的有机溶剂中具有较好的溶解性,在纯的四氢呋喃溶液中具有很强的荧光,但随着溶液中水的比例的增加溶液的荧光出现逐渐减弱的趋势,因此该化合物不具备聚集诱导发光效应。
第五章结论
Development of organic materials with large two-photon absorption and aggregation-induced emission (AIE) is a highly active area of research for the promising biophotonic application. In this dissertation, three new classes of triarylamine-based derivatives with aggregation-induced emission have been designed and synthesized, and their one- and two-photon absorption (2PA) properties and electroluminescence have been investigated.
The main contents and results are generalized as follows:
In Chapter 1, recent progress of the organic light-emitting materials with AIE or 2PA is reviewed. Then the research strategy of the dissertation is presented.
In Chapter 2, a new series of triphenylamine-based diketo-pyrrolo-pyrrole (DPP) fluoro-phores (DPP-Ⅰ, DPP-Ⅱ, DPP-Ⅲ) have been prepared, in which their strctures are D-π-A-π-A, D-π-A-π-A and D-π-A-π-D (D:donor,π:conjugated bridge, A:acceptor), respectively. And their photophysical properties have been investigated. It was found that DPP-Ⅰand DPP-Ⅱdisplayed aggregation-induced emission, while DPP-III showed aggregation-induced emission enhancement. Their values of 2PA cross section (σ) are 188,275 and 447 GM at wavelength of 800nm, respectively. DPP-Ⅲwith symmetrical structure shows the highest value of 2PA cross section.
In Chapter 3, we have developed a new class of aggregation-induced emission (AIE) active compounds, in which three electron-donating dipheylamine, phenothiazine or carbazole groups were connect to the 1,4-positions of the benzene via bis (a-cyano-4-diphenylaminostyryl conjugation bridges to form three triarylamine CNDPASB(a-c) quadrupolar derivatives. And we also synthesized the corresponding DPASB(a-c) compounds without cyano unit for the purpose of comparison. Their one- and two-photon absorption properties have been investigated. The two-photon absorption (2PA) cross sections measured by the open aperture Z-scan technique were determined to be 1016,1484 and 814 GM for CNDPASB(a-c) and 540,259 and 34 GM for DPASB(a-c), respectively. The result shows that the high 2PA properties of these molecules are attributed to the extendedπ-system and enhanced intramolecular charge transfer from starburst triarylamine to cyano group. Moreover, CNDPASB-based compounds are very weakly fluorescent in THF solution, but their intensities are increased by almost 230,70, and 5 times in the water-THF (V/V 90%) mixtures, respectively, in which they exhibit a strongly enhanced red, orange and deep-yellow color fluorescence emission, respectively. The result indicates that the intra-molecular vibration and rotation of these dyes is considerably restricted in nano-aggregates formed in water, which leads to significant increases of fluorescence. It was found that the CNDPASB-based compounds color tuning can be conveniently accomplished by alternating the starburst triarylamine donor moiety. The multi-layer electroluminescence devices with TPBI (2,2', 2"-(benzene-1,3,5-triyl)-tri(1-phenyl- 1H-benzimidazole)) electron-transporting layer have been made with CNDPASB-a and CNDPASB-c as non-doping red-yellow emitter, electron-transporting as well as hole-transporting material. CNDPASB-c showed a good stability of the light color. The luminous intensity of CNDPASB-c reached 858 cd/m2. The current efficiency attained by the EL device for CNDPASB-a and CNDPASB-c are 0.67 and 0.83 cd/A, respectively. The maximum external quantum efficiency is 0.77% and 0.33% for CNDPASB-a and CNDPASB-c, respectively.
In Chapter 4, we have synthesized a new starburst triphenylamine-based 2PA compound (TSASB-b) using the triphenylamine as the core and their photophysical properties are investigated. TSASB-b showed a good performance of 2PA and its value of 2PA cross section is 129 GM. TSASB-b has a good solubility in THF, dichloromethane and so on. The emission from the THF solution of TSASB-b was so strong, but the fluorescence gradually weakened with the increasing of the proportion of water in the solution. So TSASB-b didn't show aggregation-induced emission.
In Chapter 5,conclusion.
本论文的主要内容包括以下几个方面：
第一章综述了具有聚集诱导发光效应、双光子效应的有机光电功能材料的研究进展,并在此基础上提出了本文的设计思路和研究内容。
第二章设计合成了一类基于三苯基胺的吡咯并吡咯二酮(DPP)类衍生物,研究了该类化合物的聚集诱导发光效应和双光子性能。化合物DPP-Ⅰ和DPP-Ⅱ具有聚集诱导发光的特征,而化合物DPP-Ⅲ则表现出聚集诱导发光增强效应。三个化合物分别采用了D-π-A-π-A,D-兀-A-π-A和D-π-A-π-D(D代表给体,A代表受体)的分子结构。在80飞秒、800 nm激光的激发条件下,三个化合物的双光子吸收截面值分别为188 GM,275 GM和447 GM,其中采用对称分子结构的化合物DPP-Ⅲ具有较高的双光子吸收截面值。
第三章设计合成了一类具有聚集诱导发光效应基于星射状三芳胺和氰基的四极分子双光子材料(CNDPASB(a-c)),为了进行对比,我们也合成了没有氰基基团星射状三芳胺的化合物(DPASB(a-c))。在80飞秒、800 nm激光的激发条件下,化合物CNDPASB(a-c)的双光子吸收截面值分别为1016 GM,1484 GM和814 GM,化合物DPASB(a-c)的双光子吸收截面值分别为540 GM,259 GM和34 GM。另外,化合物CNDPASB(a-c)在溶液中荧光强度接近于零,在聚集态时则发出强烈的荧光,且荧光颜色分别呈现出红色、橙色和黄色,表现出聚集诱导发光效应,而化合物DPASB(a-c)却表现出聚集猝灭现象。将具有聚集发光性能的CNDPASB-a和CNDPASB-c制成有机电致发光二极管,CNDPASB-c器件展现出很强的深黄色荧光且具有很好光色稳定性,最大发光强度达858cd/m2。CNDPASB-a和CNDPASB-c器件的电流效率分别为0.67和0.83 cd/A,两者的最大外部量子效率分别为0.77%和0.33%。
第四章设计合成了以星射状三芳胺为封边给体,三苯胺为核的化合物(TSASB-b),测试了化合物的聚集诱导发光效应和双光子性能。在80飞秒、800 nm激光的激发条件下,化合物TSASB-b双光子吸收截面值为129 GM。化合物TSASB-b在一般的有机溶剂中具有较好的溶解性,在纯的四氢呋喃溶液中具有很强的荧光,但随着溶液中水的比例的增加溶液的荧光出现逐渐减弱的趋势,因此该化合物不具备聚集诱导发光效应。
第五章结论
Development of organic materials with large two-photon absorption and aggregation-induced emission (AIE) is a highly active area of research for the promising biophotonic application. In this dissertation, three new classes of triarylamine-based derivatives with aggregation-induced emission have been designed and synthesized, and their one- and two-photon absorption (2PA) properties and electroluminescence have been investigated.
The main contents and results are generalized as follows:
In Chapter 1, recent progress of the organic light-emitting materials with AIE or 2PA is reviewed. Then the research strategy of the dissertation is presented.
In Chapter 2, a new series of triphenylamine-based diketo-pyrrolo-pyrrole (DPP) fluoro-phores (DPP-Ⅰ, DPP-Ⅱ, DPP-Ⅲ) have been prepared, in which their strctures are D-π-A-π-A, D-π-A-π-A and D-π-A-π-D (D:donor,π:conjugated bridge, A:acceptor), respectively. And their photophysical properties have been investigated. It was found that DPP-Ⅰand DPP-Ⅱdisplayed aggregation-induced emission, while DPP-III showed aggregation-induced emission enhancement. Their values of 2PA cross section (σ) are 188,275 and 447 GM at wavelength of 800nm, respectively. DPP-Ⅲwith symmetrical structure shows the highest value of 2PA cross section.
In Chapter 3, we have developed a new class of aggregation-induced emission (AIE) active compounds, in which three electron-donating dipheylamine, phenothiazine or carbazole groups were connect to the 1,4-positions of the benzene via bis (a-cyano-4-diphenylaminostyryl conjugation bridges to form three triarylamine CNDPASB(a-c) quadrupolar derivatives. And we also synthesized the corresponding DPASB(a-c) compounds without cyano unit for the purpose of comparison. Their one- and two-photon absorption properties have been investigated. The two-photon absorption (2PA) cross sections measured by the open aperture Z-scan technique were determined to be 1016,1484 and 814 GM for CNDPASB(a-c) and 540,259 and 34 GM for DPASB(a-c), respectively. The result shows that the high 2PA properties of these molecules are attributed to the extendedπ-system and enhanced intramolecular charge transfer from starburst triarylamine to cyano group. Moreover, CNDPASB-based compounds are very weakly fluorescent in THF solution, but their intensities are increased by almost 230,70, and 5 times in the water-THF (V/V 90%) mixtures, respectively, in which they exhibit a strongly enhanced red, orange and deep-yellow color fluorescence emission, respectively. The result indicates that the intra-molecular vibration and rotation of these dyes is considerably restricted in nano-aggregates formed in water, which leads to significant increases of fluorescence. It was found that the CNDPASB-based compounds color tuning can be conveniently accomplished by alternating the starburst triarylamine donor moiety. The multi-layer electroluminescence devices with TPBI (2,2', 2"-(benzene-1,3,5-triyl)-tri(1-phenyl- 1H-benzimidazole)) electron-transporting layer have been made with CNDPASB-a and CNDPASB-c as non-doping red-yellow emitter, electron-transporting as well as hole-transporting material. CNDPASB-c showed a good stability of the light color. The luminous intensity of CNDPASB-c reached 858 cd/m2. The current efficiency attained by the EL device for CNDPASB-a and CNDPASB-c are 0.67 and 0.83 cd/A, respectively. The maximum external quantum efficiency is 0.77% and 0.33% for CNDPASB-a and CNDPASB-c, respectively.
In Chapter 4, we have synthesized a new starburst triphenylamine-based 2PA compound (TSASB-b) using the triphenylamine as the core and their photophysical properties are investigated. TSASB-b showed a good performance of 2PA and its value of 2PA cross section is 129 GM. TSASB-b has a good solubility in THF, dichloromethane and so on. The emission from the THF solution of TSASB-b was so strong, but the fluorescence gradually weakened with the increasing of the proportion of water in the solution. So TSASB-b didn't show aggregation-induced emission.
In Chapter 5,conclusion.
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