稠环芳烃材料在有机电致发光器件中的应用研究
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摘要
有机电致发光器件作为一种平板显示技术,具有诸如自发光、高亮度、宽视角、超薄、低能耗、响应速度快、可卷曲、可实现全色发光等众多优点,而备受人们的关注。通过采用适当的器件结构、器件制作技术和有机材料,有机电致发光器件的性能得到明显提高。在全色显示方面,高效率、稳定的绿色有机电致发光器件已达实用化程度,与绿色有机电致发光器件相比,蓝色和红色有机电致发光器件的效率和色纯度对于全色显示来说尤其需要提高。另一方面,白光有机电致发光器件由于其在全色显示和背光源的潜在应用价值,也备受人们的关注。尽管有机电致发光器件的有些产品已经商业化,但作为一种技术还需要不断提高其产品性能。在本论文中,有些工作已经提高了有机电致发光器件的性能。本论文的工作主要包括以下方面:
(1)探索了合成二芳香基蒽衍生物的方法,合成了三种二芳香基蒽衍生物。本文中设计的合成方法较一般传统方法具有反应步骤少,方法简便,原料易得,不需使用昂贵的钯化合物催化剂,产品产率高等特点;而且其中个别中间体3,5-二苯基溴苯的合成方法较一般传统方法也具有反应步骤少,方法简便,原料易得,产品产率高等特点,这些都具有较好的实际应用价值,为今后的工业生产提供技术支持。
本论文以自制的二芳香基蒽衍生物蓝光材料为非掺杂发光层制作了蓝色器件,研究了发光层厚度、空穴传输层厚度、电子传输层厚度对电致发光光谱的影响,进行了器件优化,并利用空穴阻挡层改善色纯度,得到色纯度好的蓝色发光。
本论文还首次以4,4’-N,N’-二咔唑基联苯(CBP)作为主体发光材料、以蒽衍生物9,10-二(β-萘基)蒽(ADN)为掺杂剂,得到深蓝色发光器件,并通过ADN掺杂浓度的优化,得到性能好的深蓝色发光器件。器件发光色坐标为(0.1516,0.0836),最高发光亮度为6500cd/m2,最大发光效率为3.5cd/A。
(2)本论文研究了三种结构的白光有机电致发光器件,以蓝色和黄色为基本色素单位混合得到白色发光,器件结构为:第三种器件所发射白光在14V时最大亮度为11665cd/m2,对应效率为2.9cd/A。研究表明,第三种器件发光层中,少量Perylene对Rubrene的发光起了促进作用,在Rubrene浓度为0. 005 mol %时,Rubrene的发光主要源于Perylene分子的能量转移,而不是Rubrene分子直接捕获载流子形成激子。比较三种结构的白光有机电致发光器件,白光色度相差不大,从器件效率、制备工艺的复杂程度等方面考虑,第三种结构的白光有机电致发光器件较好。
(3)本论文通过分子设计合成了一种新的红色有机荧光染料6,13-二(3,5-二(苯基)苯基)并五苯(PDT),并以其为发光材料制备了三种结构的有机电致发光器件,器件结构为: ITO/TPD(50nm)/PDT(60nm)/Bphen(25nm)/LiF(1nm)/Al(器件-P) ITO/TPD(50nm)/Alq3 : 3%molPDT(60nm)/Bphen(25nm)/LiF(1nm)/Al(器件-AP) ITO/TPD(50nm)/Alq3:3mol%PDT:1mol%rubrene(60nm)/Bphen(25nm)/LiF(1nm)/Al(器件-APR)尽管器件-P的发光色坐标为(0.6581,0.2927),但其电流效率较低,亮度只有几个尼特,器件性能较差。器件-AP的发光色坐标在4mA/cm2时为(0.5901,0.3804),电流效率为1.5cd/A,其色纯度较差。为了提高器件的发光性能,我们在器件-AP的发光层中再掺杂红荧烯作为辅助掺杂剂。研究表明,红荧烯不但自身发光,还帮助使能量从Alq3转移到PDT,从而得到较纯的红色发光器件,器件在120mA/cm2时电流效率为2.4cd/A,色坐标为(0.6081,0.3779)。与其它类型材料的有机电致发光器件相比,该器件色度比较稳定,电流密度在12mA/cm2到200 mA/cm2变化时,其色坐标仅由(0.612,0.371)变化到(0.6018,0.3814),这对其实际应用具有非常重要的意义。该器件中可能的激发机制,既存在由Rubrene向PDT的能量转移,也存在PDT直接捕获载流子。比较三种结构的红光有机电致发光器件,从器件色度、效率及稳定性等方面考虑,具有辅助掺杂剂的第三种结构(器件-APR)的红光有机电致发光器件较好。
(4)有机电致发光材料能带的准确测定对于有机电致发光器件研究至关重要。电化学方法(如循环伏安法)是表征有机材料的HOMO能级的简单而被广泛采用的方法之一。通常所用循环伏安法存在用料多、数值确定不明显等方面的缺点,因此我们改进了上述方法,将待测定材料在工作电极上成膜,采用线性扫描伏安法直接测定氧化电流起峰位置而得到其HOMO能级。再结合光谱数据就可以计算出材料的LUMO能级。研究表明该方法用料量少、快速、简便。
Organic light emitting devices (OLEDs) have attracted considerable attention due to their outstanding superiorities of application in flat-panel displays, such as self-luminous, high-brightness, wide viewing angle, thinness, low power consumption, fast response time, flexible, and full color. The performance of OLEDs has been improved significantly with the adoption of suitable device structures, process technologies, and organic materials. In full color display, highly efficient and stable green OLEDs have been realized. Compared with green-emitting devices, the electroluminescence (EL) characteristics of blue and red-emitting ones have to be improved particularly in terms of efficiency and color purity for full color applications. On the other hand, white light devices among various colors draw particular attention because their potential use in backlight, full color applications, as well as in lighting purposes. The products of OLEDs have been commercialized, however much work remains important to enhance the product performance. In this dissertation, some works have been shown to improve the performance of OLEDs. It includes the following items:
(1) Several 9, 10-diaryl substituted anthracene derivatives were synthesized by a simple synthetic route from anthraquinone compared with conventional method. In this way it is of less reacting steps, convenient, easy to obtain raw material, not need to use expensive palladium catalyst, and of high yield of the product. It is also shown a simple way to synthesize the intermediate product 3, 5-(diphenyl) bromobenzene by one-pot reaction of 2,4,6-tribromoiodobenzene with aryl-Grignard reagent, which is beneficial to industrial manufacture.
Blue organic light emitting devices were prepared based on undoped 9, 10-diaryl substituted anthracene derivatives as light emitting materials. The influences of the thickness of lighting layer, hole transporting layer, and electron transporting layer on emitting spectra were studied. The color purity of devices was improved by using hole blocking layer, resulting in pure blue emission. A deep blue organic light emitting diode which was fabricated by firstly using 9,10-di(2-naphthyl)anthracene (ADN) as a dopant and 4,4’-N,N’-dicarbazole- biphenyl (CBP)as a host. The doping concentration of ADN was optimized, and the Commission Internationale de l’Eclairage coordinates of (0.1516, 0.0836) were achieved in the cell, which is very close to the National Television Standards Committee standard of (0.14, 0.08). Meanwhile, maximum luminance over 6500cd/cm2 and maximum current efficiency of 3.5cd/A were also obtained.
(2) This dissertation presents organic light-emitting diodes which generate white emission based on both perylene and 5,6,11,12-tetraphenylnaphthacene (rubrene) doped in 9,10-di(2-naphthyl)anthracene (ADN). The white OLEDs have three kinds of configurations: ITO/TPD(50nm)/ADN: 0.04mol%Rubrene (40nm)/Bphen(25nm)/LiF(1nm)/Al, ITO/TPD (50nm)/ADN: 0.05mol%Rubrene (20nm)/ADN: 0.85mol%Perylene (20nm)/Bphen(25nm)/LiF(1nm)/Al, And ITO/TPD (50nm)/ADN:0.85mol%Perylene:0.005mol%Rubrene (40nm)/Bphen(25nm)/LiF(1nm)/Al. The CIE color coordinates of above devices at 4mA/cm2 are (0.3175, 0.3692), (0.3098, 0.3515) and (0.3064, 0.3888) respectively. Compared with the other two devices, the third device presents white emission with the maximum luminance of 11665cd/m2 at 14V according to luminance efficiency of 2.9cd/A. The third white organic light emitting device was fabricated by doping two color fluorescent dyes in one blue host. In which yellow emission component from rubrene was strengthened due to another dopant perylene. It was found that the blue dopant perylene not only itself emitted but also assisted the energy transfer from ADN to rubrene. Thus, in lower concentration of rubrene the white lighting emission was obtained.
(3) Three kinds of red organic light emitting devices (ROLEDs) were configured based on a new synthesized pentacene derivative, 6, 13-di-(3,5-diphenyl) phenylpentacene (PDT), doped in tris-(8-hydroxy-quinolinato)aluminum(Alq3). ITO/TPD (50nm)/PDT (60nm)/Bphen(25nm)/LiF(1nm)/Al(Cell-P) ITO/TPD (50nm)/Alq3 : 3%molPDT(60nm)/Bphen(25nm)/LiF(1nm)/Al(Cell-AP) ITO/TPD (50nm)/Alq3:3mol%PDT: 1mol%rubrene (60nm)/Bphen(25nm)/LiF(1nm)/Al (Cell-APR) Although the color coordinate is (0.6581, 0.2927) in Cell-P, the maximum luminance is 3.5cd/m2. The luminance of Cell-P is poor. While the color coordinate is (0.5901, 0.3804) at 4mA/cm2 according to luminance efficiency of 1.5cd/A in Cell-AP. In order to improve the color purity of red emission in Cell-AP, 5,6,11,12-tetraphenylnaphthacene (rubrene) was introduced as the assist dopant in above doping system (Alq3:PDT). The assist dopant (rubrene) not only itself emitted but also assisted the energy transfer from the host (Alq3) to the red emitting dopant (PDT). A stable red emission cell was obtained, and the color coordinates have only small variation from (0.612, 0.371) to (0.6018, 0.3814) with increasing the current density from 12 mA/cm2 to 200 mA/cm2. The excitation mechanism of PDT in Cell-APR may be considered to be both energy transfer from rubrene and PDT directly carrier trapping. So we may deduce that it is attributed to rubrene assist effect which is beneficial to energy transfer from Alq3 to PDT in the same emitting layer, resulting in stable red emission.
(4) It is very important to obtain accurate data of energy band structure of organic electroluminescent materials. Cyclic voltammetry is one of the methods usually used to obtain HOMO energy level. However it is too difficult to get precise data of HOMO energy level by cyclic voltammetry. In this dissertation technology of linear scanning voltammetry (LSV) is instead utilized to attain a result of oxidation potential (or HOMO energy level) due to electrochemical oxidation of organic electroluminescent material filmed on the working electrode. Fewer amounts of materials are consumed in this method. And results show that it is faster and more convenient.
(1)探索了合成二芳香基蒽衍生物的方法,合成了三种二芳香基蒽衍生物。本文中设计的合成方法较一般传统方法具有反应步骤少,方法简便,原料易得,不需使用昂贵的钯化合物催化剂,产品产率高等特点;而且其中个别中间体3,5-二苯基溴苯的合成方法较一般传统方法也具有反应步骤少,方法简便,原料易得,产品产率高等特点,这些都具有较好的实际应用价值,为今后的工业生产提供技术支持。
本论文以自制的二芳香基蒽衍生物蓝光材料为非掺杂发光层制作了蓝色器件,研究了发光层厚度、空穴传输层厚度、电子传输层厚度对电致发光光谱的影响,进行了器件优化,并利用空穴阻挡层改善色纯度,得到色纯度好的蓝色发光。
本论文还首次以4,4’-N,N’-二咔唑基联苯(CBP)作为主体发光材料、以蒽衍生物9,10-二(β-萘基)蒽(ADN)为掺杂剂,得到深蓝色发光器件,并通过ADN掺杂浓度的优化,得到性能好的深蓝色发光器件。器件发光色坐标为(0.1516,0.0836),最高发光亮度为6500cd/m2,最大发光效率为3.5cd/A。
(2)本论文研究了三种结构的白光有机电致发光器件,以蓝色和黄色为基本色素单位混合得到白色发光,器件结构为:第三种器件所发射白光在14V时最大亮度为11665cd/m2,对应效率为2.9cd/A。研究表明,第三种器件发光层中,少量Perylene对Rubrene的发光起了促进作用,在Rubrene浓度为0. 005 mol %时,Rubrene的发光主要源于Perylene分子的能量转移,而不是Rubrene分子直接捕获载流子形成激子。比较三种结构的白光有机电致发光器件,白光色度相差不大,从器件效率、制备工艺的复杂程度等方面考虑,第三种结构的白光有机电致发光器件较好。
(3)本论文通过分子设计合成了一种新的红色有机荧光染料6,13-二(3,5-二(苯基)苯基)并五苯(PDT),并以其为发光材料制备了三种结构的有机电致发光器件,器件结构为: ITO/TPD(50nm)/PDT(60nm)/Bphen(25nm)/LiF(1nm)/Al(器件-P) ITO/TPD(50nm)/Alq3 : 3%molPDT(60nm)/Bphen(25nm)/LiF(1nm)/Al(器件-AP) ITO/TPD(50nm)/Alq3:3mol%PDT:1mol%rubrene(60nm)/Bphen(25nm)/LiF(1nm)/Al(器件-APR)尽管器件-P的发光色坐标为(0.6581,0.2927),但其电流效率较低,亮度只有几个尼特,器件性能较差。器件-AP的发光色坐标在4mA/cm2时为(0.5901,0.3804),电流效率为1.5cd/A,其色纯度较差。为了提高器件的发光性能,我们在器件-AP的发光层中再掺杂红荧烯作为辅助掺杂剂。研究表明,红荧烯不但自身发光,还帮助使能量从Alq3转移到PDT,从而得到较纯的红色发光器件,器件在120mA/cm2时电流效率为2.4cd/A,色坐标为(0.6081,0.3779)。与其它类型材料的有机电致发光器件相比,该器件色度比较稳定,电流密度在12mA/cm2到200 mA/cm2变化时,其色坐标仅由(0.612,0.371)变化到(0.6018,0.3814),这对其实际应用具有非常重要的意义。该器件中可能的激发机制,既存在由Rubrene向PDT的能量转移,也存在PDT直接捕获载流子。比较三种结构的红光有机电致发光器件,从器件色度、效率及稳定性等方面考虑,具有辅助掺杂剂的第三种结构(器件-APR)的红光有机电致发光器件较好。
(4)有机电致发光材料能带的准确测定对于有机电致发光器件研究至关重要。电化学方法(如循环伏安法)是表征有机材料的HOMO能级的简单而被广泛采用的方法之一。通常所用循环伏安法存在用料多、数值确定不明显等方面的缺点,因此我们改进了上述方法,将待测定材料在工作电极上成膜,采用线性扫描伏安法直接测定氧化电流起峰位置而得到其HOMO能级。再结合光谱数据就可以计算出材料的LUMO能级。研究表明该方法用料量少、快速、简便。
Organic light emitting devices (OLEDs) have attracted considerable attention due to their outstanding superiorities of application in flat-panel displays, such as self-luminous, high-brightness, wide viewing angle, thinness, low power consumption, fast response time, flexible, and full color. The performance of OLEDs has been improved significantly with the adoption of suitable device structures, process technologies, and organic materials. In full color display, highly efficient and stable green OLEDs have been realized. Compared with green-emitting devices, the electroluminescence (EL) characteristics of blue and red-emitting ones have to be improved particularly in terms of efficiency and color purity for full color applications. On the other hand, white light devices among various colors draw particular attention because their potential use in backlight, full color applications, as well as in lighting purposes. The products of OLEDs have been commercialized, however much work remains important to enhance the product performance. In this dissertation, some works have been shown to improve the performance of OLEDs. It includes the following items:
(1) Several 9, 10-diaryl substituted anthracene derivatives were synthesized by a simple synthetic route from anthraquinone compared with conventional method. In this way it is of less reacting steps, convenient, easy to obtain raw material, not need to use expensive palladium catalyst, and of high yield of the product. It is also shown a simple way to synthesize the intermediate product 3, 5-(diphenyl) bromobenzene by one-pot reaction of 2,4,6-tribromoiodobenzene with aryl-Grignard reagent, which is beneficial to industrial manufacture.
Blue organic light emitting devices were prepared based on undoped 9, 10-diaryl substituted anthracene derivatives as light emitting materials. The influences of the thickness of lighting layer, hole transporting layer, and electron transporting layer on emitting spectra were studied. The color purity of devices was improved by using hole blocking layer, resulting in pure blue emission. A deep blue organic light emitting diode which was fabricated by firstly using 9,10-di(2-naphthyl)anthracene (ADN) as a dopant and 4,4’-N,N’-dicarbazole- biphenyl (CBP)as a host. The doping concentration of ADN was optimized, and the Commission Internationale de l’Eclairage coordinates of (0.1516, 0.0836) were achieved in the cell, which is very close to the National Television Standards Committee standard of (0.14, 0.08). Meanwhile, maximum luminance over 6500cd/cm2 and maximum current efficiency of 3.5cd/A were also obtained.
(2) This dissertation presents organic light-emitting diodes which generate white emission based on both perylene and 5,6,11,12-tetraphenylnaphthacene (rubrene) doped in 9,10-di(2-naphthyl)anthracene (ADN). The white OLEDs have three kinds of configurations: ITO/TPD(50nm)/ADN: 0.04mol%Rubrene (40nm)/Bphen(25nm)/LiF(1nm)/Al, ITO/TPD (50nm)/ADN: 0.05mol%Rubrene (20nm)/ADN: 0.85mol%Perylene (20nm)/Bphen(25nm)/LiF(1nm)/Al, And ITO/TPD (50nm)/ADN:0.85mol%Perylene:0.005mol%Rubrene (40nm)/Bphen(25nm)/LiF(1nm)/Al. The CIE color coordinates of above devices at 4mA/cm2 are (0.3175, 0.3692), (0.3098, 0.3515) and (0.3064, 0.3888) respectively. Compared with the other two devices, the third device presents white emission with the maximum luminance of 11665cd/m2 at 14V according to luminance efficiency of 2.9cd/A. The third white organic light emitting device was fabricated by doping two color fluorescent dyes in one blue host. In which yellow emission component from rubrene was strengthened due to another dopant perylene. It was found that the blue dopant perylene not only itself emitted but also assisted the energy transfer from ADN to rubrene. Thus, in lower concentration of rubrene the white lighting emission was obtained.
(3) Three kinds of red organic light emitting devices (ROLEDs) were configured based on a new synthesized pentacene derivative, 6, 13-di-(3,5-diphenyl) phenylpentacene (PDT), doped in tris-(8-hydroxy-quinolinato)aluminum(Alq3). ITO/TPD (50nm)/PDT (60nm)/Bphen(25nm)/LiF(1nm)/Al(Cell-P) ITO/TPD (50nm)/Alq3 : 3%molPDT(60nm)/Bphen(25nm)/LiF(1nm)/Al(Cell-AP) ITO/TPD (50nm)/Alq3:3mol%PDT: 1mol%rubrene (60nm)/Bphen(25nm)/LiF(1nm)/Al (Cell-APR) Although the color coordinate is (0.6581, 0.2927) in Cell-P, the maximum luminance is 3.5cd/m2. The luminance of Cell-P is poor. While the color coordinate is (0.5901, 0.3804) at 4mA/cm2 according to luminance efficiency of 1.5cd/A in Cell-AP. In order to improve the color purity of red emission in Cell-AP, 5,6,11,12-tetraphenylnaphthacene (rubrene) was introduced as the assist dopant in above doping system (Alq3:PDT). The assist dopant (rubrene) not only itself emitted but also assisted the energy transfer from the host (Alq3) to the red emitting dopant (PDT). A stable red emission cell was obtained, and the color coordinates have only small variation from (0.612, 0.371) to (0.6018, 0.3814) with increasing the current density from 12 mA/cm2 to 200 mA/cm2. The excitation mechanism of PDT in Cell-APR may be considered to be both energy transfer from rubrene and PDT directly carrier trapping. So we may deduce that it is attributed to rubrene assist effect which is beneficial to energy transfer from Alq3 to PDT in the same emitting layer, resulting in stable red emission.
(4) It is very important to obtain accurate data of energy band structure of organic electroluminescent materials. Cyclic voltammetry is one of the methods usually used to obtain HOMO energy level. However it is too difficult to get precise data of HOMO energy level by cyclic voltammetry. In this dissertation technology of linear scanning voltammetry (LSV) is instead utilized to attain a result of oxidation potential (or HOMO energy level) due to electrochemical oxidation of organic electroluminescent material filmed on the working electrode. Fewer amounts of materials are consumed in this method. And results show that it is faster and more convenient.
引文
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