蒽系衍生物發光材料之合成與應用

Synthesis and Device Properties of Anthracene Derivatives

黃建勳(Chien-Hsun Huang)

指導教授 ： 葉瑞銘

中原大學/理學院/化學研究所/碩士(2008年)

https://doi.org/10.6840/cycu200800038

摘要

本論文探討一些蒽(Anthracene) 的螢光材料衍生物 N,N,N',N'-Tetraphenyl-anthracene-9,10-diamine (JA) 、N,N,N',N'-Tetra-m-tolyl-anthracene-9,10-diamine (JM) 、N,N,N',N'-Tetra-p-tolyl-anthracene-9,10-diamine (JP) 、N,N,N',N'-Tetrakis-(3,4-dimethyl-phenyl)-anthracene-9,10-diamine (JD)之光物理、熱穩定性、及電激發光特性。實驗結果發現此一系列的有機材料烷基取代基會影響放光光色，其中以化合物JD放光波長最長。而後這些材料以ITO/HTL/dopant:ADN/ETL/LiF/Al結構製備元件，發現元件之電激發光與固態螢光吻合，光色都落在綠光區間。元件發光效率表現以化合物JD表現最佳，其CIE座標為(0.38, 0.59) ，其表現在100mA/cm2下最大亮度可到24991 cd/m2，在10000 cd/m2下最佳效率分別為9.24 lm/W和28.17 cd/A，在元件上具有非常好的電激發光特性。
此外，本研究更以JA為主軸衍生合成了JPA、TA、A26P，9,10-Bis-(Diphenyl-amine)-anthracene (JPA)、2,6-Di-tert-butyl-N,N,N',N'-tetraphenyl-anthracene-9,10-diamine (TA)、9,10,N,N,N',N'-Hexaphenyl-anthracene-2,6-diamine (A26P)。此類化合物之發光範圍除JPA發藍光其餘都發綠光。其元件表現以A26P為dopant的元件可以得到CIE座標為(0.28, 0.64) ，在100mA/cm2下最大亮度可到21501 cd/m2。在10000 cd/m2下最佳效率分別為7.64lm/W和22.84cd/A。此化合物具有不錯的發光效率和亮度和色座標，其顯現出來的光色較JA和TA純綠。在蒽的9,10-位置芳香胺上的取代基會直接影響其光色的表現；且在蒽2,6-位置上接上芳香胺比在9,10-位置上接上芳香胺，可得半波寬較窄且光色較純之光色。

關鍵字

蒽 ； 發光材料

並列摘要

The photophysics, thermostability and electroluminecene properties of anthracene derivatives including
N,N,N',N'-Tetraphenyl-anthracene-9,10-diamine (JA), N,N,N',N'-Tetra-m-tolyl-anthracene-9,10-diamine (JM),
N,N,N',N'-Tetra-p-tolyl-anthracene-9,10-diamine (JP),
and N,N,N',N'-Tetrakis-(3,4-dimethyl-phenyl)-anthracene-9,10-diamine (JD) are discussed in this study. Experimental results indicated that the substitution of alkyl groups has greatly effect on colors of the lights these anthrancene deriviates emit. Among these deriviatives, JD has the longest emittion wavelength in solutions and solid state. Emissions from these deriviatives which has been fabricated as solid device with structure of ITO/HTL/dopant:ADN/ETL/LiF/Al show the same trend as that in solutions and solid state. Compound JD has the best performance with CIE locating at (0.38, 0.59), reaching 24991 cd/m2 at 100mA/cm2 and 9.24 lm/W and 28.17 cd/A at 10000 cd/m2, respectively.
In addition, deriviatives based on structure of JA were synthezed including 9,10-Bis-(Diphenyl-amine)-anthracene (JPA),
2,6-Di -tert-butyl-N,N,N',N'-tetraphenyl-anthracene-9,10-diamine (TA),
and 9,10,N,N,N',N'-Hexaphenyl-anthracene-2,6-diamine (A26P). Emissions from the JA-derivated compounds were in green light region, exception for the JPA which emitted in blue. The best performance of these JA-derivated compounds was obtained by using A26P doped in host in which CIE at (0.28, 0.64) was observed. The maximum brightness of 21501 cd/m2 could be achieved at 100mA/cm2 while its best performance was 7.64 lm/W and 22.84 cd/A at 10000 cd/m2. Higher purity of light color would also be observed in this device. Based on experimental results, substitution at 9,10-position of anthracene would directly turn the color of the emission, while substituted at 2,6-position of anthracene by amine-deriviated groups would result in a narrower emission band and purer color.

並列關鍵字

OLED Device ； Anthracene Derivatives

參考文獻

13. 陳金鑫, 石建民, 鄧青雲, 化學, 1996, 54, 125.

2. W. Helfrich, W. G. Schneider, Phys. Rev. Lett., 1965, 14, 229.

3. C. W. Tang, S. A. VanSlyke, Appl. Phys. Lett., 1987, 51, 913.

5. T. Tsutsui, M. J. Yang, Jpn. J. Appl. Phys., 1999, 38, 1502.

1988, 27, L713.