雙極型二苄環庚烯衍生物和其芴螺旋共軛體在染料敏化太陽能電池和有機電激發光二極體之應用

王一森

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雙極型二苄環庚烯衍生物和其芴螺旋共軛體在染料敏化太陽能電池和有機電激發光二極體之應用

Ambipolar Dibenzosuberene Derivatives and Their Spirofluorene Hybrids for Dye-Sensitized Solar Cell and Organic Light-Emitting Diodes Applications

王一森 , Masters　　Advisor：陳建添　　

英文

有機電激發光二極體；染料敏化太陽能電池；雙極型；二苄環庚烯；苯并噻二唑；磷光主體材料；熱活化型延遲螢光； Organic Light-Emitting Diodes ； Dye-Sensitized Solar Cell ； Ambipolar ； Dibenzosuberene ； 2,1,3-Benzothiadiazole ； Phosphorescent host material ； Thermally activated delayed fluorescence

Abstract │ Reference (149) │ Altmetrics

Abstract 〈TOP〉

我們成功地合成出一系列以二芐環庚烯 (DBE) 為核心架構的有機染料敏化材料，在 C3 與 C7 位置接上二苯胺基與 N,N-二苯基噻吩基-2-胺作為電子予體，並在 C5 位置接上 α-cyanoacrylic acid 及不同的 π 共軛系統，得到具有 D-π-A 系統的化合物 4、8 與 13，具有 D-π-A-A 系統的化合物 22，以及具有 D-π-A-π-A 系統的化合物 26。此一系列有機染料敏化材料的最大吸收波長在 376-499 nm 之間，莫耳吸收係數在 26,300 - 56,900 M-1 cm-1 之間。在元件效率方面，表現最好的材料為化合物 26，在 AM 1.5 標準太陽光照射下元件效率 (η) 最大可達 3.28% (Voc = 633 mV, JSC = 6.78 mA/cm2, FF = 0.76)，光電轉換效率 (IPCE) 在 400-550 nm 的吸收範圍可達到54%。
我們以二苯乙烯/芴之雙重鄰位混成系統作為模板，二苯胺基做為推電子基，腈基做為拉電子基，引入在二芐環庚烯模板的 C3 及 C7 位置，與旋環芴模板的 C2’ 及 C7’ 位置，得到推拉電子基彼此間互不共軛的雙極性材料化合物 32 (N2-STIF-CN2) 與化合物 34 (CN2-STIF-N2)。以化合物 34 為主體發光材料，摻雜紅光客體發光材料 OS1 (元件結構：ITO/TAPC/CN2-STIF-N2:10% OS1/CN-STIF-CN/LiF/Al)，在 1,000 cd/m2 下的放光效能為 1.6 cd/A，功率效能為 0.81 lm/W，外部量子效率為 1.6 %，最大亮度為 15,400 cd/m2，CIE 座落於 (0.65, 0.35)。我們嘗試以 BANE 與 CBP 為主體發光材料，摻雜化合物 32 與 34為客體發光材料 (元件結構：ITO/PEDOT:PSS/host : 5% dopant/TPBI/LiF/Al)，但是並沒有觀察到熱活化型延遲螢光 (Thermally activated delayed fluorescence, TADF) 放光現象，其中以 CBP 為主體發光材料摻雜化合物 34 為客體發光材料有最好的元件效率，在電流密度為 20 mA/cm2 下，放光效能為 0.61 cd/A，功率效能為 0.29 lm/W，最大亮度為 858 cd/m2，CIE 座落於 (0.50, 0.48)。

Parallel Abstract 〈TOP〉

A new class of dibenzosuberene derivatives with diphenylamine and N,N-diphenylthiophen-2-amine as donor at C-3 and C-7 and with  α-cyanoacrylic acid and different conjugated π-system units at C-5 were synthesized as five novel D-π-A-featured compound 4, 8 and 13 D-π-A-A-featured compound 22 and D-π-A-π-A-featured compound 26 for dye-sensitized solar cell applications. These five compounds whose maximum absorption wavelength were observed at 376 nm and 499 nm, respectively, and the molar absorption coefficient were observed at 26,300 M-1 cm-1 and 56,900 M-1 cm-1, respectively. The best device performance was D-π-A-π-A-featured compound 26, and it showed a conversion efficiency (η) of up to 3.28% (Voc = 633 mV, JSC = 6.78 mA/cm2, FF = 0.76) under AM 1.5 G conditions. And the best IPCE values achieved 54% within the 400 - 550 nm absorption range.
    Besides, we developed a new class of cis-stilbene/fluorene spiro hybrid systems with ambipolar organic fluorescent materials for organic light-emitting diodes applications. We utilized sp3-C of spiro center as the molecular bridge to suppress the donor–acceptor interactions by appending diphenylamine onto the C-3 and C-7 position and cyano group onto the C-2’ and C-7’ position for compound 32 (N2-STIF-CN2) and appending diphenylamine onto the C-2’ and C-7’ position and cyano group onto the C-3 and C-7 position for compound 34 (CN2-STIF-N2). We demonstrated red-emitting PhOLED using the compound 34 as the ambipolar host material and [Os(bpftz)2(PPhMe2)2, OS1] as red dopant (i.e., ITO/TAPC/CN2-STIF-N2:10% OS1/CN-STIF-CN/LiF/Al). This device showed a maximum current efficiency of 1.6 cd/A, power efficiency of 0.81 lm/W, EQE of 1.6%, and a maximum brightness of 15,400 cd/m2 at 1,000 cd/m2 with CIE color coordinates of (0.65, 0.35). We tried to use BANE and CBP as host material and the compound 32 and 34 as dopant (i.e., ITO/PEDOT:PSS/host : 5% dopant/TPBI/LiF/Al), but there was no thermally activated delayed fluorescence (TADF) observed in compound 32 and 34. The device with CBP as host material and compound 34 as dopant showed the best performance. The device emitted yellow light and showed a maximum current efficiency of 0.61 cd/A, power efficiency of 0.29 lm/W, and a maximum brightness of 858 cd/m2 at 20 mA/cm2 with CIE color coordinates of (0.50, 0.48).

Reference ( 149 ) 〈TOP〉

(1) (a) Armaroli, N.; Balzani, V. Angew. Chem. Int. Ed. 2007, 46, 52. (b) Service, R. F. Science 2005, 309, 548.
連結：
(2) National Renewable Energy Laboratory (NREL) http://www.nrel.gov/
連結：
(10) M. Grätzel Nature 2001, 414, 338.
連結：
(11) N. Robertson Angew. Chem. Int. Ed. 2006, 45, 2338.
連結：
(12) M. Gorlov; L. Kloo Dalton Transactions 2008, 2655.
連結：

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