CN110423255B - 基于单芳基取代喹喔啉环金属铱(iii)配合物深红光电致磷光材料及其应用 - Google Patents
基于单芳基取代喹喔啉环金属铱(iii)配合物深红光电致磷光材料及其应用 Download PDFInfo
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Abstract
本发明属于有机光电材料技术领域，具体涉及一类单芳基取代的喹喔啉环金属铱(III)配合物深红光电致磷光材料及应用。以π共轭芳烃单取代的喹喔啉配体为主配体，2,2,6,6‑四甲基‑3,5‑庚二酮为辅助配体，构筑了单核环金属铱(III)配合物电致发光材料。该类配合物具有良好的溶解性、热稳定和较高的荧光量子产率。以该电致发光材料为发光层掺杂剂，PVK/OXD‑7为主体材料，制备有机电致磷光发光器件。获得了最大发射峰为673nm、外量子效率为11.43％和色坐标为(0.63,0.29)的深红光有机电致磷光发光器件，实现了单芳基取代喹喔啉为主配体的环金属铱(III)配合物的高效电致深红色发光。
Description
技术领域
本发明属于有机电致发光材料领域，特别涉及一类单芳基取代喹喔啉环金属铱(III)配合物深红光电致磷光材料及其在深红光有机电致发光器件(OLEDs)中的应用。
背景技术
过渡金属铱(III)配合物发光材料广泛应用于高效率的新型显示和照明器件的发光层中(Adv.Mater.2014,26,3844；Angew.Chem.Int.Ed.2016.55,2714)；对于其中窄带隙深红光磷光材料而言，由于受能隙规则制约，目前基于深红光电致磷光材料的种类相对较少，且发光性能较差。因此，对于深红光电致磷光材料的研究仍然是研究的热点之一。目前，对于深红光磷光材料研究较多的为含氮原子杂环配体的环金属铱(III)配合物发光材料(Adv.Mater.2011,23,2981；J.Am.Chem.Soc.2003,125,12971；Adv.Mater.2003,15,224)，而相比于上述含单氮杂原子喹啉、异喹啉类配合物发光材料，基于双氮杂喹喔啉类配合物发光波长相对较为红移。且基于喹喔啉主配体的环金属铱(III)配合物，由于其分子易修饰特点，在研究和应用领域均受到广泛关注(Synth.Met.2005,155,168；Chem.Mater.2015,27,96)，但通过对喹喔啉环的外围芳环取代研究报道较少，且喹喔啉单元具有强的电子注入特性，引入具有空穴传输特性的给电子芳环来平衡载流子传输，加强光吸收和激子利用在器件稳定性和高效率上，具有重要研究价值。
因此，通过对喹喔啉单元上的功能化取代及进行刚性构筑，获得性能优异的环金属铱(III)配合物电致发光材料，具有广阔的研究前景和应用价值。
发明内容
针对现有的深红光有机电致发光材料种类偏少和效率普遍较低，本发明通过外围芳基取代来构筑环金属铱配合物，在喹喔啉环6/7位上进行功能化，通过嫁接π共轭基团，引入具有空穴传输特性的给电子芳环来平衡载流子传输，加强光吸收和激子利用，通过加强器件稳定性和发光效率，来提高环金属铱(III)配合物的电致发光性能。本发明致力于开发单取代的π共轭芳基喹喔啉主配体，构筑深红色环金属铱属铱(III)配合物电致发光材料，为开发新型高效有机环金属铱(III)配合物深红光电致发光材料，提供一种新的思路。
本发明的目的在于提供一种π共轭芳烃单取代喹喔啉配体为主配体,2,2,6,6-四甲基-3,5-庚二酮为辅助配体，构筑一类单核环金属铱(III)配合物，该类材料具有深红光电致发光特性，可用于电致发光器件。
本发明的另一个目的在于提供了一种单芳基取代喹喔啉环金属铱(III)配合物的应用，将其作为发光层掺杂材料用于制备有机电致发光器件，可实现有机电致发光器件的深红光发射，使有机电致发光器件实现高效的光电转换效率。
本发明提供的单芳基取代喹喔啉类铱(III)配合物发光材料，具有下式所示的结构：
式中，G为下列基团中的一种；
其中，取代基G为π共轭体系的芳基取代基团；取代位置为喹喔啉单元的6位或7位。
优选的铱(III)配合物深红光材料的取代基G为1-芘基取代基。
上述单芳基取代的喹喔啉类铱配合物发光材料的结构式优选为以下化合物中一种：
本发明还提供了一种所述具有单芳基取代的喹喔啉类铱(III)配合物发光材料的应用，将所述单芳基取代的喹喔啉类铱(III)配合物发光材料作为发光层掺杂材料应用于制备近深红光有机电致发光器件。
优选的方案，所述单芳基取代的喹喔啉类铱(III)配合物发光材料与共轭高分子主体材料复合制备深红光有机电致发光器件的发光层。
较优选的方案，具有π共轭芳烃单取代的喹喔啉非对称单核环金属铱(III)配合物的质量为共轭高分子主体材料质量的0.5～4％。
进一步优选的方案，共轭高分子主体材料为PVK和OXD-7混合物。
本发明采用的器件结构为ITO/PEDOT:PSS(40nm)/poly-TPD(30nm)/[(PVK:OXD-7)]:complex(wt％,60nm)/DPEPO(10nm)/TmPyPB(40nm)/CsF(1.2nm)/Al(120nm)。
本发明的具有π共轭芳烃单取代喹喔啉的非对称单核环金属铱(III)配合物的具体合成路线如下：
优选的铱配合物深红光材料G为1-芘基；取代位置为喹喔啉单元的6或7位,以合成式II和式III结构芘取代喹喔啉的非对称单核环金属铱(III)配合物为例进行具体说明:
本发明的其它单取代的单核环金属铱(III)配合物可以参考式II和式III结构的环金属铱(III)配合物的合成方法，仅需替换原料即可实现。
本发明提出的单功能基取代的喹喔啉为主配体的非对称单核环金属铱(III)配合物深红光电致磷光材料，基于其中式II和式III配合物所制备的器件性能表现为最大外量子效率分别为11.43％和10.48％。
有益效果：
本发明中配合物具有不同位置芳基取代结构，有利于研究喹喔啉类材料的有效共轭延伸，通过简单缩合反应，Suzuki偶联反应，桥连及去桥连反应即可得到对应化合物，且基于该类材料高的外量子效率，在OLED中应用前景光明。
附图说明
图1为本发明中化合物Ir-1的单晶结构图。
图2为本发明中化合物Ir-2的单晶结构图。
图3为本发明中化合物Ir-1的紫外-可见吸收光谱图。
图4为本发明中化合物Ir-1的光致发光光谱图。
图5为本发明中化合物Ir-2的紫外-可见吸收光谱图。
图6为本发明中化合物Ir-2的光致发光光谱图。
图7为本发明中化合物Ir-1的电致发光光谱图。
图8为本发明中化合物Ir-1的J-V-R曲线。
图9为本发明中化合物Ir-1的EQE曲线图。
图10为本发明中化合物Ir-1的EC曲线图。
图11为本发明中化合物Ir-2的电致发光光谱图。
图12为本发明中化合物Ir-2的J-V-R曲线。
图13为本发明中化合物Ir-2的EQE曲线图。
图14为本发明中化合物Ir-2的EC曲线图。
具体实施方式
实施例1
1-芘取代的喹喔啉非对称单核环金属铱(III)配合物深红光电致磷光材料的合成路线如下。其中，中间体M3的合成方法参照文献(Zhaoran Hao,Fanyuan Meng,Pu Wang,etal.,Dalton Trans.,2017,46,16257-16268.)。
6-溴-3-甲基-2-苯基喹喔啉【M1】与6-溴-2-甲基-3-苯基喹喔啉【M2】的合成
在100mL单口瓶中依次加入1,2-二氨基-4-溴苯(2.5g,17.2mmol)，1-苯基-1,2-丙二酮(3.2g,17.2mmol)，乙醇(40mL)，加热至沸腾，反应24h，停止反应，减压蒸馏除去溶剂，粗产品以PE-THF(V/V,20/1)为洗脱剂，进行柱层析分离，得到无色晶状固体【M1】2.2g，产率：38.6％；1H NMR(400MHz,CDCl3)δ8.25(s,1H),7.98(d,J＝8.9Hz,1H),7.80(d,J＝8.7Hz,1H),7.66(d,J＝6.4Hz,2H),7.60-7.49(m,3H),7.27(s,1H),2.78(s,3H).MALDI-TOF MS(m/z)for C15H11BrN12.Calcd:298.011；Found:300.097；
同时得到无色晶状固体【M2】(2.9g,50.9％):1H NMR(400MHz,CDCl3)δ8.29(s,1H),7.92(d,J＝8.8Hz,1H),7.81(d,J＝8.7Hz,1H),7.65(d,J＝6.6Hz,2H),7.53(d,J＝6.8Hz,3H),2.77(s,3H).MALDI-TOF MS(m/z)for C15H11BrN12.Calcd:298.011；Found:300.104.
3-甲基-2-苯基-6-(1-芘基)喹喔啉【L1】的合成
在50mL单口瓶中依次加入化合物M1(0.54g,1.81mmol)，芘-1-联硼酸频那醇酯(M30.59g,1.81mmol)，碳酸钾的水溶液(2M,5mL)，Pd(Pph3)4(62mg,0.054mmol)和四氢呋喃(15mL)，加热至沸腾，氮气保护下反应24h,停止反应，冷却至室温，将粗产品倒入50mL水中，DCM萃取(3×25mL),有机相用无水MgSO4干燥，过滤，减压蒸馏除去溶剂，粗产品以PE-THF(V/V,25/1)为洗脱剂，进行柱层析分离，得到黄绿色固体0.48g，产率：63.1％；1H NMR(400MHz,CDCl3)δ8.37-8.19(m,3H),8.16-8.01(m,3H),7.73(d,J＝5.2Hz,1H),7.57(d,J＝7.2Hz,1.5H),2.85(s,1.5H).13C NMR(101MHz,CDCl3)δ155.01,153.15,142.91,141.22,140.27,139.03,136.23,132.44,131.44,130.98,129.55,129.10,129.01,128.65,128.48,128.01,127.82,127.39,126.16,125.40,124.99,124.86,124.82,24.53.MALDI-TOF MS(m/z)for C15H11BrN12.Calcd:420.163；Found:422.272.
2-甲基-3-苯基-6-(1-芘基)喹喔啉【L2】的合成
方法同【L1】的合成，得白色固体0.45g，产率：58.9％；1H NMR(400MHz,CDCl3)δ8.42(s,1H),8.26(dd,J＝18.1,6.6Hz,5H),8.15-8.04(m,6H),7.72(s,2H),7.55(d,J＝7.3Hz,3H),2.87(s,3H).13C NMR(101MHz,CDCl3)δ155.43,152.69,142.39,140.97,140.48,139.02,136.20,132.90,131.44,131.02,130.92,130.43,129.09,128.99,128.61,128.47,128.13,127.97,127.76,127.37,126.13,125.37,125.07,124.99,24.48.MALDI-TOF MS(m/z)for C15H11BrN12.Calcd:420.163；Found:422.272.
环金属铱(III)配合物【Ir-1】的合成
在25mL单口瓶中依次加入化合物L1(100mg,0.24mmol)，IrCl3·H2O(24mg,0.08mmol)和2-乙二醇乙醚/水(3/1mL)，加热至沸腾，氮气保护下反应24h，停止反应，冷却至室温，将悬浊液过滤，依次用水及少量的甲醇洗涤滤饼，减压干燥，得到桥连体粗产物(pmqx)2Ir(μ-Cl)2Ir(pmqx)2【M4】(120mg)；将所得桥连体M4，2,2,6,6-四甲基-3,5-庚二酮(177mg,0.96mmol)，碳酸钾(200mg,1.24mmol)和2-乙二醇乙醚(5mL)依次加入到25mL单口瓶中，于90℃下氮气氛围中反应24h；停止反应，冷却至室温，将粗产品倒入20mL水中，DCM萃取(3×10mL)；有机相用无水MgSO4干燥，过滤，减压蒸馏除去溶剂，粗产品以PE-DCM-THF(V/V/V,50/10/1)为洗脱剂，进行柱层析分离，得到紫红色固体【Ir-1】16mg，产率：24.7％；1HNMR(400MHz,CDCl3)δ8.28(d,J＝9.7Hz,9H),8.25-8.18(m,6H),8.13(s,5H),8.05(d,J＝7.3Hz,4H),7.65(d,J＝7.9Hz,2H),7.12(s,2H),6.81(s,4H),5.06(s,1H),3.39(s,6H),0.76(s,18H).13C NMR(101MHz,CDCl3)δ194.99,164.67,155.39,152.22,146.00,142.00,140.77,139.68,137.47,135.99,132.94,131.50,131.09,130.96,129.23,128.93,128.87,128.43,127.97,127.86,127.81,127.43,126.18,125.46,125.12,124.89,121.31,89.22,40.66,27.92,27.15.MALDI-TOF MS(m/z)for C73H57IrN4O2.Calcd:1214.411；Found:1215.723.
环金属铱(III)配合物【Ir-2】的合成
方法同配合物【Ir-1】，得紫红色固体【2】，产率：29.5％；1H NMR(400MHz,CDCl3)δ8.40(s,2H),8.32(d,J＝6.7Hz,2H),8.16(dd,J＝13.2,7.4Hz,4H),8.11-7.99(m,14H),7.92(d,J＝7.9Hz,2H),7.83(d,J＝5.7Hz,2H),7.71(s,2H),7.28(s,2H),7.04(s,2H),6.92(s,2H),4.57(s,1H),3.27(s,6H),1.58(s,18H).13C NMR(101MHz,CDCl3)δ195.04,164.82,156.69,151.63,146.45,142.66,138.54,137.50,136.08,132.14,131.37,130.93,130.66,129.24,128.72,128.22,127.70,127.48,127.33,125.87,124.99,124.81,124.78,124.72,124.60,121.40,88.91,39.76,26.91,26.78.MALDI-TOF MS(m/z)for C73H57IrN4O2.Calcd:1214.411；Found:1215.718.
实施例2
1-芘取代的喹喔啉类铱(III)配合物的光物理性能表征及其单发光层聚合物电致发光器件的制作和发光性能的测试。
1-芘取代的喹喔啉类铱(III)配合物的1H NMR、13C NMR谱通过Bruker Dex-400NMR仪器测定，单晶结构由Bruker SMART Apex CCD单晶衍射仪测定，紫外-可见吸收光谱及光致发光光谱通过CARY100紫外-可见光谱仪及Perkin-Elmer LS-50荧光光谱仪测定，电化学性能由CHI620voltammetric电化学工作站测得，基态及激发态能级及轨道分布经由高斯09程序包实施。
1-芘取代的喹喔啉类铱(III)配合物磷光材料的单发光层聚合物电致发光器件包括：氧化锡铟(ITO)导电玻璃、聚二氧乙基噻吩：聚对乙烯苯磺酸钠(PEDOT：PSS)阳极材料、聚[双(4-苯基)(4-丁基苯基)胺](poly-TPD)空穴传输层，发光层由主体材料和磷光材料构成(5mg/mL，氯苯溶液)，其中主体材料为PVK/OXD-7，磷光材料为本发明优选材料其中一种磷光材料，掺杂材料在主体材料中的质量百分比(x％)为0.5％～4.0％；二(2-二苯氧化膦基)二苯醚(DPEPO)空穴阻挡层，1,3,5-三[(3-吡啶基)-3-苯基]苯(TmPyPB)电子传输层，阴极由氟化锂(LiF)层和铝(Al)层构成。
制作的聚合物电致发光器件的结构如下：
ITO/PEDOT:PSS(40nm)/poly-TPD(30nm)/[(PVK:OXD-7)7:3]:complex(x wt％,60nm)/DPEPO(10nm)/TmPyPB(40nm)/CsF(1.2nm)/Al(120nm)。
器件的制作程序：在处理好的ITO玻璃上，先后旋转涂敷40nm PEDOT：PSS阳极材料、30nm空穴传输层poly-TPD，45nm发光层，然后依次真空蒸镀10nm空穴阻挡层DPEPO和40nm的电子传输层TmPyPB，然后依次蒸镀1.2nm的CsF层和120nm的Al层。
电子阻挡层和发光层的膜厚用表面轮廓仪(Tencor,ALFA-Step500)测定。Al的厚度和沉积速度用厚度/速度仪(Sycon公司的STM-100厚度/速度仪)测定，Al的沉积速度分别为1～2nm/s。所有的操作都在氮气手套箱中进行。
聚合物发光器件的电致发光光谱通过PR-705光谱分析仪测定，电流-电压特性通过由Kethiey 236测定。
实施例3
环金属铱(III)配合物【Ir-1】与环金属铱(III)配合物【Ir-2】的单晶分子结构如图1和图2所示，通过单晶分析，确证了两个异构化的配合物【Ir-1】和【Ir-2】的分子结构正确。
实施例4
环金属铱(III)配合物【Ir-1】的光物理性能。
配合物【Ir-1】在二氯甲烷溶液中的紫外吸收光谱如图3所示。其中在230-410nm区间的吸收归属于配体内自旋允许的π-π*电子跃迁1LC，492nm的吸收归属于配体内的电子跃迁单线态和三线态金属之间电子跃迁(1MLCT/3MLCT)；图4是配合物【Ir-1】的光致发光光谱，其最大发光波长为673nm，归属于深红色发光。其紫外吸收、光致发光、荧光量子效率以及低温磷光寿命见表1.配合物【Ir-1】的荧光量子效率和低温磷光寿命分别为2.59％和1.13μs。
实施例5
环金属铱(III)配合物【Ir-2】的光物理性能。
配合物【Ir-2】在二氯甲烷溶液中的紫外吸收光谱如图5所示。其中在230-406nm区间的吸收归属于配体内自旋允许的π-π*电子跃迁1LC，494nm的吸收归属于配体内的电子跃迁单线态和三线态金属之间电子跃迁(1MLCT/3MLCT)；图6是配合物【Ir-2】的光致发光光谱，其最大发光波长为669nm，归属于深红色发光。其紫外吸收、光致发光、荧光量子效率以及低温磷光寿命见表1.配合物【Ir-2】的荧光量子效率和低温磷光寿命分别为4.30％和1.18μs。
实施例6
环金属铱(III)配合物【Ir-1】做掺杂剂的单发光层聚合物电致发光器件性能。
在0.5％～4.0％不同质量掺杂浓度下，配合物【Ir-1】掺杂PVK/OXD-7的聚合物电致发光器件，在不同掺杂浓度下的电致发光光谱(EL)曲线和不同电流密度下的J-V-R曲线如图7和图8所示。当掺杂浓度为0.5％时，器件的最大电致发射峰位于672nm,随着掺杂浓度的增大，最大电致发射峰初步红移，当掺杂浓度为4％时，器件的最大电致发射峰位于675nm，归属于深红色电致发光；自图8可知，但掺杂浓度为0.5％时，器件的启亮电压为7.6V，当电流密度为18.41mA/cm2，其最大发光亮度为753cd/m2；图9和图10分别配合物【Ir-1】在不同掺杂浓度下的外量子效率(EQE)和电流效率(CE)曲线，当配合物【Ir-1】在掺杂浓度为0.5％，器件的EQE和CE分别为11.43％和1.98ca/A。
实施例7
环金属铱(III)配合物【Ir-2】做掺杂剂的单发光层聚合物电致发光器件性能。
在0.5％～4.0％质量掺杂浓度下，配合物【Ir-2】掺杂PVK/OXD-7的聚合物电致发光器件，在不同掺杂浓度下的电致发光光谱(EL)曲线和不同电流密度下的J-V-R曲线如图11和图12所示。当掺杂浓度为0.5％时，器件的最大电致发射峰位于672nm,随着掺杂浓度的增大，最大电致发射峰发生红移，当掺杂浓度为4％时，器件的最大电致发射峰位于675nm，归属于深红色电致发光；自图12可知，当掺杂浓度为1.0％时，器件的启亮电压为7.5V，当电流密度为18.41mA/cm2，其最大发光亮度为1115cd/m2；图13和图14分别配合物【Ir-2】在不同掺杂浓度下的外量子效率(EQE)和电流效率(CE)曲线，当配合物【Ir-2】在掺杂浓度为0.5％，器件的EQE和CE分别为10.48％和2.24ca/A。
表1配合物Ir-1和Ir-2的光物理性能数据
a Measured in 2-MeTHF solution to concentrations～10-5at r.t.bΦp isthe absolute photoluminescence quantum yields in degassed 2-MeTHF,τis theexcited-state lifetime,all measurement was conducted at excition wavelengthof 480nm.c Measured in CH2Cl2solution to concentrations～10-5at 77K.
表2配合物Ir-1和Ir-2的电致发光性能数据
a Turn-on voltage at a brightness of 1cd/m2.b Current density at amaximum radiant.c The maximum radiant intensity.d Current density at maximumefficiencies.e The maximum current efficiency.f The maximum external quantumefficiency.
尽管结合了优选实施例对本发明进行了说明，但本发明并不局限于上述实施例，应当理解所附权利要求概括了本发明的范围。在本发明构思的指导下，本领域的技术人员应当意识到，对本发明的各实施例方案所进行的一定的改变，都将被本发明的权利要求书的精神和范围所覆盖。
Claims (7)
1.一类基于单芳基取代喹喔啉环金属铱(Ⅲ)配合物，其特征在于，所述环金属铱(III)配合物具有下式所示的分子结构；
式-I。
2.一种根据权利要求1所述的基于单芳基取代喹喔啉环金属铱(Ⅲ)配合物的应用，其特征在于：所述铱(Ⅲ)配合物作为发光层掺杂材料应用于制备深红光有机电致发光器件。
3.根据权利要求2所述的基于单芳基取代喹喔啉环金属铱(Ⅲ)配合物应用，其特征在于：所述的基于单芳基取代喹喔啉金属铱(Ⅲ)配合物与共轭高分子主体材料复合制备深红光有机电致发光器件的发光层。
4.根据权利要求3所述的基于单芳基取代喹喔啉环金属铱(Ⅲ)配合物应用，其特征在于：所述的基于单芳基取代喹喔啉金属铱(Ⅲ)配合物的质量为共轭高分子主体材料质量的0.5~4.0%。
5.根据权利要求3或4所述的基于单芳基取代喹喔啉环金属铱(Ⅲ)配合物应用，其特征在于：所述的共轭高分子主体材料为PVK和OXD-7的混合物。
6.根据权利要求2所述的基于单芳基取代喹喔啉环金属铱(Ⅲ)配合物应用，其特征在于，所述深红光有机电致发光器件的结构为ITO/PEDOT:PSS 40 nm/poly-TPD 30 nm/[(PVK: OXD-7) 7: 3]: 环金属铱配合物60 nm/DPEPO 10 nm/TmPyPB 40 nm/CsF 1.2 nm/Al 120 nm。
7.根据权利要求2所述的基于单芳基取代喹喔啉环金属铱(Ⅲ)配合物应用，其特征在于，所述深红光有机电致发光器件为外量子效率高达11.43%的深红色有机电致发光二极管。
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| CN108558953A (zh) * | 2018-06-05 | 2018-09-21 | 长春海谱润斯科技有限公司 | 一种含金属的有机络合物及其有机发光器件 |
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| CN104844658A (zh) * | 2014-02-18 | 2015-08-19 | 环球展览公司 | 有机电致发光材料和装置 |
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