含有喹啉和香豆素的蓝色发光材料的合成及性能

doi:10.3969/j.issn.1000-1565.2021.04.007

摘要/Abstract

摘要： 合成了一种含有喹啉和香豆素基团且发射蓝光的发光材料(QCC),通过紫外-可见吸收光谱和荧光发射光谱对QCC的光物理性质进行了测试.结果表明QCC的最大吸收峰为330 nm,且在360~540 nm内具有强的荧光发射带.随着溶剂极性的增加,QCC的荧光发射峰出现明显的红移.通过荧光猝灭技术分别观察了QCC与电子给体(DMA)和电子受体(DMTP)之间的相互作用,结果表明QCC具有优良的电子转移性能.进一步研究了QCC与碳70(C₇₀)和碳纳米管(CNTs)的相互作用.利用高斯(Gaussian)09软件计算了QCC的电子能级分布情况,所得理论计算结果与电化学循环伏安法测得的结果基本一致.此外,QCC展示了良好的热稳定性,其热分解温度(t_d)为270 ℃.上述所得结果表明,QCC可作为潜在的蓝色有机发光二极管器件的发光材料.

关键词: 香豆素, 喹啉, 蓝光发射, 性质, 电子转移

Abstract: A blue luminescent material named QCC that contains quinoline and coomarin units was synthesized. The photophysical property of QCC was investigated by the UV-vis absorption and fluorescence emission spectra, which indicates that QCC can emit blue light. With the increase of polarity of solvents, the emission wavelength of DCC shows an obvious red-shift. Besides, we investigated the interactions between QCC and electron donor N, N'-dimethylaniline(DMA), electron acceptor(DMTP)using fluorescence quenching technique, which demonstrates that QCC has excellent electron transfer property. At the same time, the interactions of QCC with C₇₀ and CNTs were also investigated to confirm the above property, respectively. The electrochemical property and energy levels of QCC were calculated by Gaussian 09 software, and the results basically conform with the data measured by cyclic voltammetry method.Thermal stability study reveals that QCC has good thermal stability with thermal decomposition temperature(t_d)of 270 ℃. These results indicate the QCC has the potential in the construction and application of blue organic light emitting diodes(OLEDs).

Key words: coumarin, quinoline, blue light emission, property, electron transfer

中图分类号:

O625.6

王晓菊,周思荣,王云侠. 含有喹啉和香豆素的蓝色发光材料的合成及性能[J]. 河北大学学报(自然科学版), 2021, 41(4): 384-389.

WANG Xiaoju,ZHOU Sirong,WANG Yunxia. Synthesis and properties of a novel blue luminescent material based on quinoline and coumarin units[J]. Journal of Hebei University(Natural Science Edition), 2021, 41(4): 384-389.

参考文献

[1] MA Z H, DONG W Y, HOU J H, et al. Dendritic host materials with non-conjugated adamantane cores for efficient solution-processed blue thermally activated delayed fluorescence OLEDs[J]. Journal Material Chemistry C, 2019, 7(38):11845-11850. DOI: 10.1039/c9tc04143e.
[2] SHAO S Y, HU J, WANG X D, et al. Blue thermally activated delayed fluorescence polymers with nonconjugated backbone and through-space charge transfer effect[J]. Journal of the American Chemical Society, 2017, 139(49): 17739-17742. DOI: 10.1021/jacs.7b10257.
[3] HU J, LI Q, WANG X D, et al. Developing through-space charge transfer polymers as a general approach to realize full-color and white emission with thermally activated delayed fluorescence[J]. Angewandte Chemie International Edition, 2019, 58(25): 8405-8409. DOI: 10.1002/anie.201902264.
[4] KIM K H, MOON C K, LEE J H, et al. Highly efficient organic light-emitting diodes with phosphorescent emitters having high quantum yield and horizontal orientation of transition dipole moments[J]. Advanced Materials, 2014, 26(23): 3844-3847. DOI: 10.1002/adma.201305733.
[5] LEUGN M Y, TANG M C, CHEUNG W L, et al. Thermally stimulated delayed phosphorescence(TSDP)-based gold(Ⅲ)complexes of tridentate pyrazine-containing pincer ligand with wide emission color tunability and their application in organic light-emitting devices[J]. Journal of the American Chemical Society, 2020, 142(5): 2448-2459. DOI: 10.1021/jacs.9b12136.
[6] SUN H, TAN X, SANG S L, et al. A novel design strategy for deeper blue and more stable thermally activated delayed uorescent emitters[J]. Organic Electronics, 2020, 78: 105610. DOI: 10.1016/j.orgel.2019.105610.
[7] WANG X, ZHONG Z M, ZHAO S, et al. An efficient blue emitter based on a naphthalene indenofluorene core[J]. Organic Electronics, 2018, 55: 157-164. DOI: 10.1016/j.orgel.2018.01.024.
[8] PENG F, ZHONG Z M, MA Y W, et al. Achieving highly efficient blue light-emitting polymers by incorporating a styrylarylene amine unit[J]. Journal Material Chemistry C, 2018, 6(45): 12355-12363. DOI: 10.1039/c8tc04411b.
[9] ZHANG T, YE J Y, LUO A S, et al. Efficient deep blue emitter based on carbazole-pyrene hybrid for non-doped electroluminescent device[J]. Optical Materials, 2020, 100: 109632. DOI: 10.1016/j.optmat.2019.109632.
[10] LIU J C, ZHONG X M, XU Y N, et al. Green synthesis of 8-hydroxyquinoline barium as visible-light-excited luminescent material using mechanochemical activation method[J]. Global Challenges, 2019, 3(12): 1900052. DOI: 10.1002/gch2.201970121.
[11] SIODEK A, ZYCH D, MARON A, et al. Fluorene vs carbazole substituent at quinoline core toward organic electronics[J]. Dyes and Pigments, 2019, 166: 98-106. DOI:10.1016/j.dyepig.2019.03.032.
[12] KING A J, ZATSIKHA Y V, BLESSENER T, et al. Ultrafast electron-transfer in a fully conjugated coumarin-ferrocene donor-acceptor dyads[J]. Journal of Organometallic Chemistry, 2019, 887: 86-97. DOI: 10.1016/j.jorganchem.2019.03.004.
[13] BU M J, LU G P, CAI C. Visible-light photoredox catalyzed cyclization of aryl alkynoates for the synthesis of trifluoromethylated coumarins[J]. Catalysis Communications, 2018, 114: 70-74. DOI: 10.1016/j.catcom.2018.06.009.
[14] ARAFA R K, HEGAZY G H, PIAZZA G A, et al. Synthesis and in vitro antiproliferative effect of novel quinoline-based potential anticancer agents[J]. European Journal of Medicinal Chemistry, 2013, 63: 826-832. DOI: 10.1016/j.ejmech.2013.03.008.
[15] ISLAM A S M, BHOWMICK R, MOHAMMAD H, et al. A novel 8-hydroxyquinoline-pyazole based highly sensitive and selective Al(Ⅲ)sensor in purely aqueous medium with intracellular application: experimental and computational studies[J]. New Journal of Chemistry, 2016, 40(5): 4710-4719. DOI: 10.1039/c5nj03153b. (