芳香胺类有机电致发光材料的合成与性能研究
摘要
芳香胺类材料是一类重要的有机电致发光材料，三芳香胺类分子和N-芳香基咔唑类分子通常具有空穴传输能力。本文通过分子设计合成，将高度刚性和空间位阻大的萘基团引入三芳香胺和N-芳香基咔唑体系，并通过材料表征和发光器件制备、测试，对基于芳香胺类的红色有机电致发光材料和蓝色有机电致发光材料进行了探索。
在本论文中，我们合成制备了一系列基于芳香胺和异佛尔酮的红色有机电致发光材料：a)基于三芳香胺和异佛尔酮的材料；b)基于咔唑和异佛尔酮的材料；c)基于三芳香胺、苯并噻唑和异佛尔酮的材料。通过~1HNMR、IR光谱、MS谱和元素分析对材料进行了化学表征；并通过紫外可见吸收(UV-Vis)光谱、光致发光(PL)光谱、循环伏安(CV)法、扫描隧道显微镜(STM)和原子力显微镜(AFM)对材料的性质进行了测试；应用以上材料作为主体发光材料或掺杂发光材料，制备得到了一系列具有较高发光性能的红色电致发光器件。
本文合成制备了一系列基于三芳香胺和苯并噻唑的蓝色发光材料，a)BPPA(即N-((4-苯并噻唑)苯基)-N-苯基苯胺)；b)BPPNA(即N-((4-苯并噻唑)苯基)-N-苯基萘胺)；c)BBPA(即4-(苯并噻唑)-N-(4-(苯并噻唑)苯基)-N-苯基苯胺)；d) BBPNA(即4-(苯并噻唑)-N-(4-(苯并噻唑)苯基)-N-苯基萘胺)。通过~1HNMR、IR光谱、MS谱和元素分析对材料进行了化学表征；并通过UV-Vis光谱、PL光谱、CV法和STM对材料的性质进行了测试；并将此类材料作为主体发光材料引入蓝色有机电发光器件中。器件ITO／NPB／BBPA／TPBI／Al具有较高的发光亮度和发光效率，器件的发光峰值为454 nm，色坐标为(x=0.19，v=0.25)，在外加16 V直流电压时达到3610 cd m~(-2)的发光亮度，在20 mA cm~(-2)电流密度下，器件的发光亮度为1048 cd m~(-2)，光度效率5.24 cd~(-1)，光功率效率1.21 lm W~(-1)，外量子效率2.88％。同类型材料BBPNA作为蓝光材料应用于器件ITO／NPB／BBPNA／TPBI／LiF／Al也表现极好的发光性能，器件的发光峰值为460 nm，色坐标为(x=0.19，y=0.22)，在外加16.5V直流电压时达到3821 cd m~(-2)的发光亮度，在20 mA cm~(-2)电流密度下，器件的发光亮度为293 cdm~(-2)，光度效率1.47 cd A~(-1)，光功率效率0.61 lm W~(-1)，外量子效率0.77％。在器件ITO／NPB／BBPNA／LiF／Al中，材料-BBPNA作为发光层和电子传输层应用于发光器件中，在外加直流电压13.0V时，得到1430 cd m~(-2)的发光亮度。
Materials based on arylamine are one of the most important materials for organic electroluminescent diodes (OLEDs). Molecules with triarylamine or N-aryl carbazole introduced in always show good hole-transporting ability. This dissertation focused on the synthesis of organic electroluminescent materials with high performance and fabrication of OLEDs with bright luminance and high efficiency. Molecules based on triarylamine and N-aryl carbazole were synthesized with naphthyl group introduced in. Red OLEDs and blue OLEDs were fabricated with these compounds as the emitting materials.
Arylamine and isophorone derivatives as red organic electroluminescent materials studied in this dissertation are divided into the following series: a) triarylamine and isophorone derivatives (compound DPN-2CN, DPN-4CN and DNP-2CN); b) N-aryl carbazole and isophorone derivatives (compound PCz-2CN, PCz-4CN and NCz-2CN); c) triarylamine, benzothiazole and isophorone derivatives (compound BPPA-2CN and BPPNA-2CN). The chemical structures of these molecules were confirmed by ~1HNMR, IR, MS and elemental analysis. The performance of them were studied by UV-Vis absorption spectra, photoluminescence (PL) spectra, cyclic voltammetric (CV) experiments, scanning probe microscopy (STM) and atomic force microscopy (AFM). Two kinds of OLEDs, Dye-doped red OLEDs and Non-doped red OLEDs, were fabricated to study the electroluminescent properties of these materials. Devices fabricated with DPN-2CN, DNP-2CN, NCz-2CN, BPPA-2CN or BPPNA-2CN as the red emitter showed good EL performance.
A series of blue electroluminescent materials based on triarylamine and benzothizole were designed and synthesized in this dissertation, N-(4-(benzo [d]thiazol-2-yl)phenyl)-N-phenylbenzenamine (BPPA), N-(4-(benzo[d]thiazol-2-yl) phenyl)-N-phenylnaphthalen-1-amine (BPPNA), 4-(benzo[d]thiazol-2-yl)-N-(4-(benzo[d]thiazol-2-yl)phenyl)-N-phenylbenzenamine (BBPA), N,N-bis(4-(benzo [d]thiazol-2-yl)phenyl)naphthalen-1-amine (BBPNA). The chemical structures of BPPA, BPPNA, BBPA and BBPNA were confirmed by ~1HNMR, IR, MS and elemental analysis. The characteristics of them were investigated by UV-Vis absorption spectra, PL spectra, CV experiments and STM. Non-doped blue OLEDs were fabricated with these materials as the blue emitter. Bright luminance and high efficiency were obtained for device with BBPA or BBPNA as the blue emitting layer. Device ITO/ NPB/ BBPA/ TPBI/ Al showed a brightness of 3610 cd m~(-2) at the driving voltage of 16 V. The emission peak of this device is 454 nm and the CIE coordinates is (x = 0．19, y = 0．25) . A brightness of 1048 cd m~(-2) , a current efficiency of 5．24 cd A~(-1) , a power efficiency of 1．21 lm W~(-1) and an external quantum efficiency of 2．88% at a driving current density of 20 mA cm~(-2) were obtained for this device. Compound BBPNA has the similar structure with BBPA. BBPNA has N,N-diphenylnaphthalen-1-amine as the electron-donor while BBPA has triphenylamine. Device ITO/ NPB/ BBPNA/ TPBI/ LiF/ Al showed a brightness of 3821 cd m~(-2) at the driving voltage of 16．5 V. The emission peak of this device is 460 nm and the CIE coordinates is (x = 0．19, y = 0．22) . A brightness of 293 cd m~(-2) , a current efficiency of 1．47 cd A~(-1) , a power efficiency of 0．61 lm W~(-1) and an external quantum efficiency of 0．77% at a driving current density of 20 mA cm~(-2) were obtained for this device. Device ITO/ NPB/ BBPNA/ LiF/ Al, with BBPNA as the emitting layer and electron transporting layer showed a brightness of 1430 cd m~(-2) at the driving voltage of 13．0 V.
在本论文中，我们合成制备了一系列基于芳香胺和异佛尔酮的红色有机电致发光材料：a)基于三芳香胺和异佛尔酮的材料；b)基于咔唑和异佛尔酮的材料；c)基于三芳香胺、苯并噻唑和异佛尔酮的材料。通过~1HNMR、IR光谱、MS谱和元素分析对材料进行了化学表征；并通过紫外可见吸收(UV-Vis)光谱、光致发光(PL)光谱、循环伏安(CV)法、扫描隧道显微镜(STM)和原子力显微镜(AFM)对材料的性质进行了测试；应用以上材料作为主体发光材料或掺杂发光材料，制备得到了一系列具有较高发光性能的红色电致发光器件。
本文合成制备了一系列基于三芳香胺和苯并噻唑的蓝色发光材料，a)BPPA(即N-((4-苯并噻唑)苯基)-N-苯基苯胺)；b)BPPNA(即N-((4-苯并噻唑)苯基)-N-苯基萘胺)；c)BBPA(即4-(苯并噻唑)-N-(4-(苯并噻唑)苯基)-N-苯基苯胺)；d) BBPNA(即4-(苯并噻唑)-N-(4-(苯并噻唑)苯基)-N-苯基萘胺)。通过~1HNMR、IR光谱、MS谱和元素分析对材料进行了化学表征；并通过UV-Vis光谱、PL光谱、CV法和STM对材料的性质进行了测试；并将此类材料作为主体发光材料引入蓝色有机电发光器件中。器件ITO／NPB／BBPA／TPBI／Al具有较高的发光亮度和发光效率，器件的发光峰值为454 nm，色坐标为(x=0.19，v=0.25)，在外加16 V直流电压时达到3610 cd m~(-2)的发光亮度，在20 mA cm~(-2)电流密度下，器件的发光亮度为1048 cd m~(-2)，光度效率5.24 cd~(-1)，光功率效率1.21 lm W~(-1)，外量子效率2.88％。同类型材料BBPNA作为蓝光材料应用于器件ITO／NPB／BBPNA／TPBI／LiF／Al也表现极好的发光性能，器件的发光峰值为460 nm，色坐标为(x=0.19，y=0.22)，在外加16.5V直流电压时达到3821 cd m~(-2)的发光亮度，在20 mA cm~(-2)电流密度下，器件的发光亮度为293 cdm~(-2)，光度效率1.47 cd A~(-1)，光功率效率0.61 lm W~(-1)，外量子效率0.77％。在器件ITO／NPB／BBPNA／LiF／Al中，材料-BBPNA作为发光层和电子传输层应用于发光器件中，在外加直流电压13.0V时，得到1430 cd m~(-2)的发光亮度。
Materials based on arylamine are one of the most important materials for organic electroluminescent diodes (OLEDs). Molecules with triarylamine or N-aryl carbazole introduced in always show good hole-transporting ability. This dissertation focused on the synthesis of organic electroluminescent materials with high performance and fabrication of OLEDs with bright luminance and high efficiency. Molecules based on triarylamine and N-aryl carbazole were synthesized with naphthyl group introduced in. Red OLEDs and blue OLEDs were fabricated with these compounds as the emitting materials.
Arylamine and isophorone derivatives as red organic electroluminescent materials studied in this dissertation are divided into the following series: a) triarylamine and isophorone derivatives (compound DPN-2CN, DPN-4CN and DNP-2CN); b) N-aryl carbazole and isophorone derivatives (compound PCz-2CN, PCz-4CN and NCz-2CN); c) triarylamine, benzothiazole and isophorone derivatives (compound BPPA-2CN and BPPNA-2CN). The chemical structures of these molecules were confirmed by ~1HNMR, IR, MS and elemental analysis. The performance of them were studied by UV-Vis absorption spectra, photoluminescence (PL) spectra, cyclic voltammetric (CV) experiments, scanning probe microscopy (STM) and atomic force microscopy (AFM). Two kinds of OLEDs, Dye-doped red OLEDs and Non-doped red OLEDs, were fabricated to study the electroluminescent properties of these materials. Devices fabricated with DPN-2CN, DNP-2CN, NCz-2CN, BPPA-2CN or BPPNA-2CN as the red emitter showed good EL performance.
A series of blue electroluminescent materials based on triarylamine and benzothizole were designed and synthesized in this dissertation, N-(4-(benzo [d]thiazol-2-yl)phenyl)-N-phenylbenzenamine (BPPA), N-(4-(benzo[d]thiazol-2-yl) phenyl)-N-phenylnaphthalen-1-amine (BPPNA), 4-(benzo[d]thiazol-2-yl)-N-(4-(benzo[d]thiazol-2-yl)phenyl)-N-phenylbenzenamine (BBPA), N,N-bis(4-(benzo [d]thiazol-2-yl)phenyl)naphthalen-1-amine (BBPNA). The chemical structures of BPPA, BPPNA, BBPA and BBPNA were confirmed by ~1HNMR, IR, MS and elemental analysis. The characteristics of them were investigated by UV-Vis absorption spectra, PL spectra, CV experiments and STM. Non-doped blue OLEDs were fabricated with these materials as the blue emitter. Bright luminance and high efficiency were obtained for device with BBPA or BBPNA as the blue emitting layer. Device ITO/ NPB/ BBPA/ TPBI/ Al showed a brightness of 3610 cd m~(-2) at the driving voltage of 16 V. The emission peak of this device is 454 nm and the CIE coordinates is (x = 0．19, y = 0．25) . A brightness of 1048 cd m~(-2) , a current efficiency of 5．24 cd A~(-1) , a power efficiency of 1．21 lm W~(-1) and an external quantum efficiency of 2．88% at a driving current density of 20 mA cm~(-2) were obtained for this device. Compound BBPNA has the similar structure with BBPA. BBPNA has N,N-diphenylnaphthalen-1-amine as the electron-donor while BBPA has triphenylamine. Device ITO/ NPB/ BBPNA/ TPBI/ LiF/ Al showed a brightness of 3821 cd m~(-2) at the driving voltage of 16．5 V. The emission peak of this device is 460 nm and the CIE coordinates is (x = 0．19, y = 0．22) . A brightness of 293 cd m~(-2) , a current efficiency of 1．47 cd A~(-1) , a power efficiency of 0．61 lm W~(-1) and an external quantum efficiency of 0．77% at a driving current density of 20 mA cm~(-2) were obtained for this device. Device ITO/ NPB/ BBPNA/ LiF/ Al, with BBPNA as the emitting layer and electron transporting layer showed a brightness of 1430 cd m~(-2) at the driving voltage of 13．0 V.
引文
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