雙二甲基苯基硼化合物之合成及在有機發光二極體上的應用

Synthesis of Bis(2,6-dimethylphenyl)boron Compounds and Their Application in OLEDs

曾志富(Chih-Fu Tseng)

指導教授 ： 陳秋炳

國立清華大學/理學院/化學系/碩士(2008年)

https://doi.org/10.6843/NTHU.2008.00354

摘要

我們透過C-N coupling和C-B coupling的方式，成功地合成出雙二甲基苯基硼化合物FNB01~FNB07(六種)。此系列化合物具有不錯的熱穩定性，Tg溫度為100~141 0C，而且有好的成膜性。依不同π軌域共軛程度，此系列化合物在固態薄膜下的放光從藍光456 nm到綠光510 nm，而且在不同極性溶劑下，具有溶劑效應(solvent effect)，也就是會受到極性的溶劑影響，放光波長會紅位移(red shift)。此外，在正已烷溶劑下，螢光量子產率高達81~99 %。在元件製作上，此系列化合物當作非摻雜發光層，具有高的藍光純度，非常接近NTSC所訂定藍光位置(0.14,0.08)，而且有非常窄的半高波寬(FWHM)約44~69 nm。以FNB01、FNB04和FNB07當發光層材料所做出來元件結果，元件B： ITO/m-MTDATA(10)/NPB(30)/FNB01(20)/TPBI(10)/ Alq3(30) /LiF/Al，元件外部量子效率(ηext)為3.42 %，電流效率(ηc)為2.65 cd/A，最大亮度(Lmax)為13320 cd/m2，CIE座標為(0.14,0.08)；元件F：ITO/m-MTDATA(10)/NPB(30)/FNB04(30)/ TPBI(10)/Alq3(30)/ LiF/ Al，元件外部量子效率(ηext)為5.02 %，電流效率(ηc)為3.99 cd/A，最大亮度(Lmax)為8617 cd/m2，CIE座標為(0.13,0.09)；元件I：ITO/m-MTDATA(10)/NPB(30)/FNB07(30)/ TPBI(10)/Alq3(30)/LiF/ Al，元件外部量子效率(ηext)為2.82 %，電流效率(ηc)為2.81 cd/A，最大亮度(Lmax)為11216 cd/m2，CIE座標為(0.14,0.11)。

關鍵字

有機電激發光 ； 藍色螢光材料 ； 硼化合物

並列摘要

We synthesized compounds based on C-N coupling and C-B coupling, and we synthesized six kinds of bis(2,6-dimethylphenyl) boron compounds successfully. They were FNB01~FNB07, respectively. This series compound had good thermal stability, and Tg temperatures were 100~141 0C. Moreover, they formed good thin-film readily. According to different π orbital conjugate ability, this series compounds in solid state PL emission from 456 nm to 510 nm. Moreover, this series compounds showed strongly solvent-dependent emission band, and we called solvent effect. In other words, the emission spectrums of these compounds shift toward a longer wavelength with the increasing polarity of the solvents. By in n-hexane solvent, the fluorescence quantum yield reached 81% to 99%. In the devices, this series compounds used as non-doped emission layers, had high blue light purity, and extremely approaches NTSC to subscribe decided the true blue light coordinates of (0.14, 0.08). Moreover, they had extremely narrowly full-width-half-maximum (FWHM), about 44 nm to 69 nm. We used FNB01, FNB04, and FNB07 as emission layers. Device B: ITO/ m-MTDATA(10)/NPB(30)/FNB01(20)/TPBI(10)/Alq3(30) /LiF/Al, this device can achieve a external quantum efficiency(ηext) of 3.42%, current efficiency(ηc) of 2.65 cd/A, maximum brightness(Lmax) of 13320 cm/m2, and CIE coordinates of (0.14,0.08). Device F: ITO/m-MTDATA(10)/NPB(30)/FNB04(30) /TPBI(10)/Alq3(30)/LiF/Al, this device can achieve a higher external quantum efficiency (ηext) of 5.02%, current efficiency(ηc) of 3.99 cd/A, maximum brightness (Lmax) of 8617 cm/m2, and CIE coordinates of (0.13, 0.09). Device I: ITO/m-MTDATA(10)/NPB(30)/FNB07(30) /TPBI(10)/Alq3(30)/LiF/Al, this device can achieve a lower external quantum efficiency(ηext) of 2.82%, current efficiency(ηc) of 2.81 cd/A, a higher maximum brightness(Lmax) of 11216 cm/m2, and CIE coordinates of (0.14, 0.11).

並列關鍵字

OLED ； blue fluorescence materials ； boron compounds

參考文獻

25. J. S. Huang, M. Pfeiffer, A. Werner, J. Blochwitz, K. Leo, S. Y. Liu, Appl. Phys. Lett. 2002, 81, 922.

14. Shi, J.; Tang, C. W.; Chen, C. H. US 5,646,948, 1997.

40. X. H. Zhou, Y. H. Niu, F. Huang, M. S. Liu, K. Y. Jen, Macromolecule, 2007, 40, 3015.

28. T. H. Huang, J. T. Lin, L. Y. Chen, Y. T. Lin, C. C. Wu, Adv. Mater. 2006, 18, 602.

45. C. C. Wu, Y. T. Lin, K. T. Wong, R. T. Chen, Y. Y. Chien, Adv. Mater. 2004, 16, 61.