CN104817540A - 一种菲并咪唑衍生物及其应用 - Google Patents
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Abstract
本发明公开了一种菲并咪唑衍生物,具有较高的三重态能量,高玻璃化温度,以及良好的电子/空穴传输能力。当其作为电子传输材料使用时,与现有技术中常用的电子传输材料BCP为电子传输基团的传统主体材料相比较,电子的传输能力有明显提高,在有机电致发光器件中,该化合物与传统的电子传输材料相比在玻璃化温度,电流效率,功率效率,外量子效率以及滚降方面都有显著的提高,是理想的电子传输材料。
Description
技术领域
本发明属于光电材料领域,更具体地,涉及一种菲并咪唑衍生物及其应用。
背景技术
有机电致发光现象最早发现于1963年,当时利用有机蒽晶体作为发光材料,由于该器件驱动电压高达400V,且器件效率和寿命远不及无机电致发光器件,当时并未引起人们的重视。1987年,邓青云(Tang,C.W.et al.Appl.Phys.Lett.1987,52,913)研究小组首次提出了有机多层非晶体薄膜的OLED结构;1990年Burroughes等人(Burroughes,J.H.et al.Nature.1990,347,539)首次报道了高分子发光二极管,自此有机电致发光研究进入了一个全新的阶段。近十年来,有机发光二极管因具有响应快、亮度高、工作电压低等优点而被应用于优质平面显示器中(Journal of the AmericanChemical Society,2002,124,11576;Journal of Display Technology,2005,1,90;Molecular Electronics and Bioelectronics.2007,18,25)。
要获得性能优异的OLED器件,首先要选择迁移率足够优秀的传输材料,保证在发光层中电子空穴能够平衡,然而电子传输材料是目前非常紧缺,Alq3以其较好的稳定性被广泛应用,但是由于其较低迁移率,很难制备出高效的OLED器件。
现有的电子传输材料电子迁移率仍有待改进,发展高迁移率电子传输材料为制备高效的OLED器件始终是我们研究的热点。
发明内容
针对现有技术的以上缺陷或改进需求,本发明提供了一种菲并咪唑衍生物及其应用,其目的在于提供一种电子迁移率高的电子传输材料,由此解决OLED器件电子传输材料其电子迁移率仍有待改善的技术问题。
为实现上述目的,按照本发明的一个方面,提供了一种菲并咪唑衍生物,其具有式(I)的结构:
其中,R1、R2、R3和R4为氢原子或拉电子基团,R1、R2、R3和R4相同或不同。
优选地,所述的菲并咪唑衍生物,其所述拉电子基团选自以下基团:
优选地,所述的菲并咪唑衍生物,其所述R3和R4为氢原子。
按照本发明的另一方面,提供了一种所述菲并咪唑衍生物的应用,其用作发光电子传输材料。
按照本发明的另一方面,提供了一种有机电致发光器件,包括多层有机材料,其中传输层或发光层材料包括所述菲并咪唑衍生物。
总体而言,通过本发明所构思的以上技术方案与现有技术相比,能够取得下列有益效果:
本发明提供的具有通式(I)所示结构的化合物是一类具有较高的三重态能量,高玻璃化温度,以及良好的电子/空穴传输能力。当其作为电子传输材料使用时,与现有技术中常用的电子传输材料BCP为电子传输基团的传统主体材料相比较,电子的传输能力有明显提高,在有机电致发光器件中,该化合物与传统的电子传输材料相比在玻璃化温度,电流效率,功率效率,外量子效率以及滚降方面都有显著的提高,是理想的电子传输材料。
本发明首次将菲并咪唑电子传输基团用于荧光电子传输材料中,合成了一系列的不对称的电子传输材料。例如,以CNPI-p3Py为电子传输材料,制备的荧光蓝光主体材料,其器件最大电流效率,功率效率以及外量子效率分别达到了11.12cd/A,7.23lm/w和5.66%。合成的材料具有很高的玻璃化温度,较高的三重态能量,且具有较好的空穴和电子传输能力,在荧光蓝光器件中显示出优越的效率。
附图说明
图1是菲并咪唑类电子传输材料的合成路线图;
图2是实施例7至9电子传输材料制备器件结构示意图;
图3是实施例10电子传输材料的亮度-电流密度-电压特性曲线图;
图4是实施例10电子传输材料的器件电流效率与电流密度的特性曲线图;
图5是实施例10电子传输材料的器件的电致发光特性曲线图;
图6是吡啶取代菲并咪唑电子传输材料电子迁移率曲线。
具体实施方式
为了使本发明的目的、技术方案及优点更加清楚明白,以下结合附图及实施例,对本发明进行进一步详细说明。应当理解,此处所描述的具体实施例仅仅用以解释本发明,并不用于限定本发明。此外,下面所描述的本发明各个实施方式中所涉及到的技术特征只要彼此之间未构成冲突就可以相互组合。
本发明提供的菲并咪唑衍生物,其具有式(I)的结构:
其中,R1、R2、R3和R4为氢原子或拉电子基团,R1、R2、R3和R4相同或不同。所述拉电子基团,优选为强拉电子基团,如吡啶、嘧啶、三嗪、1,2,4-噻二唑,苯并咪唑,恶二唑、恶唑、***、菲啰啉等。所述拉电子基团选自以下基团:
优选地,所述菲并咪唑衍生物其R3和R4为氢原子。更优选地,述菲并咪唑衍生物R1选自吡啶,嘧啶,苯并咪唑,R2选自吡啶,嘧啶,苯并咪唑,进一步地,具有以下结构:
本发明提供的菲并咪唑衍生物可以以菲醌为原料,通过闭环反应制得。合成路线见图1,菲并咪唑类电子传输材料的合成路线,反应条件:i)苯胺,溴代苯甲醛,醋酸钾,乙酸,120℃,12小时;ii)甲苯,乙醇,碳酸钾水溶液(2M),Pd(PPh3)4,24小时。
本发明提供的菲并咪唑衍生物,电子迁移率能够达到10-3cm2V-1s-1左右,极大的提高电子传输材料的迁移率,用作发光电子传输材料,实现载流子平衡,从而使得器件的稳定性和效率都得到大幅度的提升。
本发明同时提供了一种电致发光器件,包括多层有机材料,其中传输层或发光层材料包括本发明提供的菲并咪唑衍生物。
以下为实施例:
实施例1
一种菲并咪唑衍生物,其具有式(I)的结构,其中R1为吡啶即R2为氢原子,R3为氢原子,R4为氢原子;其化学命名为2-(4-(3-吡啶)苯基)-1-苯基-1H-[9,10-d]菲并咪唑,简称CPI-p3Py,结构式如下:
其制备方法如下:在氮气条件保护下,将化合物2-(4-溴苯基)-1-苯基-1H-[9,10-d]菲并咪唑(1)(1.76g,4.0mmol),3-硼酸吡啶(0.50g,4.0mmol),甲苯(100ml),无水乙醇(50ml),2M K2CO3(50ml)水溶液依次加入干燥的500ml两口圆底烧瓶中,超声30分钟,在氮气的条件下,将反应加热至80℃,搅拌回流24小时,待反应冷却至室温,加入二氯甲烷(60ml)萃取三次,收集有机相用水(50ml)洗涤三次,并将有机相用无水硫酸镁干燥12小时,过滤,柱层析(展开剂:乙酸乙酯和石油醚)得到白色固体2-(4-(3-吡啶)苯基)-1-苯基-1H-[9,10-d]菲并咪唑(CPI-p3Py)1.53g。产率:86%。1H-NMR(CDCl3,400MHz):δ(ppm)8.937~8.918(d,1H),8.854~8.849(d,1H),8.798~8.777(d,1H),8.738~8.717(d,1H),8.619~8.604(d,1H),7.875~7.855(d,1H),7.800~8.653(m,7H),7.587~7.514(m,5H),7.382~7.350(m,1H),7.289~7.270(t,1H),7.215~7.195(d,1H)。13C-NMR(CDCl3,400MHz):δ(ppm)150.09,148.48,148.11,138.72,137.91,137.49,135.77,134.29,130.31,129.98,129.94,129.35,129.12,128.35,128.33,127.35,127.14,126.85,126.33,125.74,125.02,124.14,123.59,123.15,122.98,122.78,120.88。MS(APCI)(m/z):[M+H+]calcd forC32H22N3:448.17,found,448.12。
实施例2
一种菲并咪唑衍生物,其具有式(I)的结构,其中R1为吡啶即R2为氢原子,R3为氢原子,R4为氢原子;其化学命名为2-(3-(3-吡啶)苯基)-1-苯基-1H-[9,10-d]菲并咪唑,简称CPI-m3Py,结构式如下:
合成过程与化合物CPI-p3Py相同,得到白色固体2-(3-(3-吡啶)苯基)-1-苯基-1H-[9,10-d]菲并咪唑(CPI-m3Py)1.50g。产率:84%。1H-NMR(CDCl3,400MHz):δ(ppm)8.933~8.913(d,1H),8.799~8.778(d,1H),8.738~8.717(d,1H),8.628~8.611(d,2H),7.777~7.660(m,8H),7.599~8.534(m,4H),7.463~7.434(t,1H),7.296~7.235(m,3H)。13C-NMR(CDCl3,400MHz):δ(ppm)150.19,148.61,148.18,138.82,137.64,137.44,134.37,131.29,130.36,129.98,129.37,129.20,129.13,128.33,128.27,128.04,127.43,127.36,127.16,126.35,125.74,125.05,124.16,123.57,123.16,122.97,122.76,120.91。MS(APCI)(m/z):[M+H+]calcd for C32H22N3:448.17,found,448.09。
实施例3
一种菲并咪唑衍生物,其具有式(I)的结构,其中R1为氢原子,R2为吡啶即R3为氢原子,R4为氢原子;其化学命名为2-(4-(3-吡啶)苯基)-1-苯基-1H-[9,10-d]菲并咪唑,简称NPI-p3Py,结构式如下:
合成过程与化合物CPI-p3Py相同,得到白色固体2-(4-(3-吡啶)苯基)-1-苯基-1H-[9,10-d]菲并咪唑(NPI-p3Py)1.46g。产率:82%。1H-NMR(CDCl3,400MHz):δ(ppm)9.031~9.025(d,1H),8.939~8.920(d,1H),8.813~8.792(d,1H),8.746~8.704(t,2H),8.045~8.025(d,1H),7.838~7.761(m,3H),7.689~7.619(m,5H),7.557~7.531(m,1H),7.489~7.458(m,1H),7.360~7.284(m,5H)。13C-NMR(CDCl3,400MHz):δ(ppm)151.03,149.28,148.31,139.10,138.56,137.42,135.04,134.51,130.31,129.83,129.54,129.34,129.01,128.58,128.34,128.31,128.02,127.38,127.11,126.37,126.37,125.76,125.02,124.22,123.78。MS(APCI):calcd for C32H22N3:448.17,found,448.16。
实施例4
一种菲并咪唑衍生物,其具有式(I)的结构,其中R1为氢原子,R2为吡啶即R3为氢原子,R4为氢原子;其化学命名为1-(3-(3-吡啶)苯基)-2-苯基-1H-[9,10-d]菲并咪唑,简称NPI-m3Py,结构式如下:
合成过程与化合物CPI-p3Py相同,得到白色固体1-(3-(3-吡啶)苯基)-2-苯基-1H-[9,10-d]菲并咪唑(NPI-m3Py)1.44g。产率:81%。1H-NMR(CDCl3,400MHz):δ(ppm)8.945~8.925(d,1H),8.847~8.801(t,2H),8.751~8.730(d,1H),8.648~8.638(d,1H),7.879~7.693(m,6H),7.641~7.535(m,4H),7.399~7.284(m,6H)。13C-NMR(CDCl3,400MHz):δ(ppm)150.95,149.28,148.17,139.92,139.43,137.35,134.94,134.48,130.82,130.21,129.56,129.38,129.10,128.59,128.34,127.86,127.58,127.40,127.04,126.39,125.79,125.06,124.27,123.75,123.13,122.89,120.77。MS(APCI)(m/z):[M+H+]calcdfor C32H22N3:448.17,found,448.13。
实施例5
一种菲并咪唑衍生物,其具有式(I)的结构,其中R1为吡啶即R2为吡啶即R3为氢原子,R4为氢原子;其化学命名为1,2-二(4-(3-吡啶)苯基)-1H-[9,10-d]菲并咪唑,简称CNPI-p3Py,结构式如下:
合成过程与化合物CPI-p3Py相同,得到白色固体1,2-二(4-(3-吡啶)苯基)-1H-[9,10-d]菲并咪唑(CNPI-p3Py)1.69g。产率:79%。1H-NMR(CDCl3,400MHz):δ(ppm)9.053~9.049(d,1H),8.919~8.715(m,5H),8.616~8.605(d,1H),8.072~8.052(d,1H),7.891~7.871(d,3H),7.789~7.676(m,6H),7.564~7.544(d,3H),7.501~7.469(m,1H),7.488~7.284(m,3H)。13C-NMR(CDCl3,400MHz):δ(ppm)150.20,149.39,148.68,148.34,148.05,139.33,138.58,138.05,137.65,135.73,134.61,134.49,134.34,132.11,132.05,130.20,130.03,129.84,129.34,129.22,128.87,128.63,128.51,128.36,128.29,127.42,127.10,126.50,126.43,125.85,125.14,124.25,123.80,123.17,122.91,122.82,120.81。MS(APCI):calcd for C37H25N4:525.61,found,525.47。
实施例6
一种菲并咪唑衍生物,其具有式(I)的结构,其中R1为吡啶即R2为吡啶即R3为氢原子,R4为氢原子;其化学命名为1,2-二(3-(3-吡啶)苯基)-1H-[9,10-d]菲并咪唑,简称CNPI-m3Py,结构式如下:
合成过程与化合物CPI-p3Py相同,得到白色固体1,2-二(3-(3-吡啶)苯基)-1H-[9,10-d]菲并咪唑(CNPI-m3Py)1.73g。产率:83%。1H-NMR(CDCl3,400MHz):δ(ppm)8.920~8.900(d,1H),8.857~8.852(d,1H),8.799~8.778(d,1H),8.729~8.708(d,1H),8.632~8.625(d,2H),8.593~8.584(d,1H),7.930~7.910(d,2H),7.859~7.839(d,1H),7.807~7.631(m,8H),7.552~7.529(m,2H),7.457~7.438(t,1H),7.372~7.311(m,4H)。13C-NMR(CDCl3,400MHz):δ(ppm)150.23,149.46,148.71,148.25,148.14,140.31,139.63,137.74,137.61,135.94,134.84,134.45,134.28,131.18,131.06,129.44,129.21,129.10,128.66,128.52,128.36,128.16,128.11,127.72,127.55,127.42,127.13,126.45,125.85,125.16,124.29,123.77,123.54,123.18,122.88,122.80,120.80。MS(APCI):calcd for C37H25N4:525.61,found,525.58。
实施例7:CPI-p3Py作为电子传输材料制备器件。
这个实例展示了CPI-p3Py作为电子传输材料而制备的电致发光器件的性能验证。本实施例的菲并咪唑衍生物作为多层有机电致发光器件的结构如图2所示(图2中标明了上述的3种化合物,在器件制作过程中只选取其中的一种),ITO(氧化铟锡)玻璃相继在清洗剂和去离子水中以超声波清洗30分钟。然后真空干燥2小时(105℃),再将ITO(氧化铟锡)玻璃放入等离子反应器中进行5分钟的氧等离子处理,传送到真空室内制备有机膜和金属电极,接着通过真空蒸发的方法制备一层10nm的空穴注入材料三氧化钼接着蒸镀80nm厚的空穴传输材料:TAPC,然后在此空穴传输层上继续通过真空蒸镀上一层12nm的蓝光发光的材料MADN:2wt%BUBD-1,最后再蒸镀一层15nm的本发明的电子传输材料(CPI-p3Py)和LiF(1nm)/Al(100nm)。
实施例8:NPI-p3Py作为电子传输材料制备器件。
这个实例展示了NPI-p3Py作为电子传输材料而制备的电致发光器件的性能验证。本实施例的菲并咪唑衍生物作为多层有机电致发光器件的结构如图2所示(图2中标明了上述的3种化合物,在器件制作过程中只选取其中的一种),ITO(氧化铟锡)玻璃相继在清洗剂和去离子水中以超声波清洗30分钟。然后真空干燥2小时(105℃),再将ITO(氧化铟锡)玻璃放入等离子反应器中进行5分钟的氧等离子处理,传送到真空室内制备有机膜和金属电极,接着通过真空蒸发的方法制备一层10nm的空穴注入材料三氧化钼接着蒸镀80nm厚的空穴传输材料:TAPC,然后在此空穴传输层上继续通过真空蒸镀上一层12nm的蓝光发光的材料MADN:2wt%BUBD-1,最后再蒸镀一层15nm的本发明的电子传输材料(NPI-p3Py)和LiF(1nm)/Al(100nm)。
实施例9:CNPI-p3Py作为电子传输材料制备器件。
这个实例展示了CNPI-p3Py作为电子传输材料而制备的电致发光器件的性能验证。本实施例的菲并咪唑衍生物作为多层有机电致发光器件的结构如图2所示(图2中标明了上述的3种化合物,在器件制作过程中只选取其中的一种),ITO(氧化铟锡)玻璃相继在清洗剂和去离子水中以超声波清洗30分钟。然后真空干燥2小时(105℃),再将ITO(氧化铟锡)玻璃放入等离子反应器中进行5分钟的氧等离子处理,传送到真空室内制备有机膜和金属电极,接着通过真空蒸发的方法制备一层10nm的空穴注入材料三氧化钼接着蒸镀80nm厚的空穴传输材料:TAPC,然后在此空穴传输层上继续通过真空蒸镀上一层12nm的蓝光发光的材料MADN:2wt%BUBD-1,最后再蒸镀一层15nm的本发明的电子传输材料(CNPI-p3Py)和LiF(1nm)/Al(100nm)。
实施例10:实施例1至6的六种化合物制作的器件的性能参数见表2。
表2实施例1至6的六种化合物作为电子传输体材料的电致发光性质
实施例1至6的六种化合物作为电子传输材料的亮度—电流密度-电压特性曲线图见图3。
实施例1至6的六种化合物作为电子传输材料的器件效率与电流密度的特性曲线图见图4。
实施例1至6的六种化合物作为电子传输材料的器件的电致发光特性曲线图见图5。
实施例1至6的六种化合物吡啶取代菲并咪唑电子传输材料电子迁移率曲线。
所述菲并咪唑衍生物的电子迁移率在10-7-10-3cm2/Vs左右,说明通过有效的调节菲并咪唑衍生物的***拉电子基团可以获得高迁移率的电子传输材料,与传统使用的电子传输材料BPhen高出两个数量级左右。
本领域的技术人员容易理解,以上所述仅为本发明的较佳实施例而已,并不用以限制本发明,凡在本发明的精神和原则之内所作的任何修改、等同替换和改进等,均应包含在本发明的保护范围之内。
Claims (5)
1.一种菲并咪唑衍生物,其特征在于,其具有式(I)的结构:
其中,R1、R2、R3和R4为氢原子或拉电子基团,R1、R2、R3和R4相同或不同。
2.如权利要求1所述的菲并咪唑衍生物,其特征在于,所述拉电子基团选自以下基团:
3.如权利要求1所述的菲并咪唑衍生物,其特征在于,所述R3和R4为氢原子。
4.一种如权利要求1至3任意一项所述菲并咪唑衍生物的应用,其特征在于,用作发光电子传输材料。
5.一种有机电致发光器件,其特征在于,包括多层有机材料,其中传输层或发光层材料包括如权利要求1至3任意一项所述的菲并咪唑衍生物。
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