CN1680366A - 一种二齿配体及其铱配合物和铱配合物的电致磷光器件 - Google Patents

一种二齿配体及其铱配合物和铱配合物的电致磷光器件 Download PDF

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CN1680366A
CN1680366A CN 200510018134 CN200510018134A CN1680366A CN 1680366 A CN1680366 A CN 1680366A CN 200510018134 CN200510018134 CN 200510018134 CN 200510018134 A CN200510018134 A CN 200510018134A CN 1680366 A CN1680366 A CN 1680366A
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CN100348594C (zh
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杨楚罗
张小伟
秦金贵
曹镛
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Wuhan University WHU
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Abstract

本发明公开了一种含咔唑单元的二齿配体及其铱配合物及基于铱配合物的聚合物型电致磷光器件。本发明的配体为含空穴传输基团咔唑基的二齿配体，铱配合物的化学式为Ir(C^N) 2 (acac)，acac＝乙酰丙酮。本发明的电致发光器件，包括导电玻璃衬底层，空穴注入层，发光层，阴极层，其中发光层的掺杂材料为二齿配体的铱配合物。本发明的二齿配体与已公开配体相比，通过引入空穴传输基团咔唑，平衡了铱配合物的载流子传输能力，提高了器件的亮度和效率。本发明可通过重金属铱和咔唑的不同位置配位，调节发光波长范围可达到84nm，可广泛应用于有机电致发光领域。

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一种二齿配体及其铱配合物和铱配合物的电致磷光器件
技术领域
本发明涉及有机电致发光材料领域，尤其涉及一种重金属元素铱配合物发光材料。
背景技术
随着信息时代的到来，显示器在仪器、计算机、通讯设备、家用电器等领域得到广泛应用，传统的阴极射线管和液晶显示器因为其自身的不足已经越来越不能满足人们的需要。比如：前者体积大、响应慢、效率低，后者也存在着视角小、响应慢、工艺复杂、被动式发光等缺点。
1987年，美国柯达公司的C.W.Tang(Appl.Phys.Lett.1987，51，913)报道了在双层有机薄膜结构中，以8-羟基喹啉铝(Alq3)为发光材料，得到低驱动电压(10V)，高亮度(1000cd/m2)，高效率(1.5lm/w)的有机电致发光器件(OLED)，使有机电致发光研究取得突破性进展。1990年J.H.Burroughes等(Nature，1990，347，539)采用PPV成功的制备发光二极管 标志着聚合物发光器件的研制取得开拓性成就。有机电致发光逐渐成为发光领域的研究热点之一。
与传统的显示技术相比，有机电致发光具有以下明显的优势：
(1)有机发光二极管是通过电流驱动有机薄膜来发光的，既可发出红、绿、蓝等单色光，也可以达到全彩色的效果，而且显示效果比液晶显示器更清晰、柔和。
(2)全固化的主动发光，而且可以制作在在塑料等一些柔性的衬底上。
(3)无视角限制，反应速度更快。
(4)材料选择范围宽，造价更低，重量更轻，耗电量更少。
常见的有机电致发光材料可分为有机小分子和聚合物。根据自旋量子统计理论，单重态激子和三重态激子的形成概率比例是1∶3，即单重态激子仅占“电子-空穴对”的25％。普通的荧光发光材料只能利用单重态激子辐射衰减发光，其电致发光的最大量子效率为25％。但是，磷光材料既能利用单重态激子，又能利用三重态激子，理论上，利用磷光染料制作的OLED内量子效率可达100％。以Os、Ru、Pd、Pt、Ir和Au这些具有d6特征的重金属原子为中心的有机金属配位化合物，旋轨耦合可以得到显著提高。这些重金属原子本身的原子跃迁并不发光，但它们能量最低的激发态通常是三重态的金属到配体的能量转移(3MLCT)，使磷光寿命大大缩短(＜100μs)。强的旋轨耦合使系间窜跃的几率大大提高(＞99％)，使激发单重态和三重态混合在一起，这样化合物的单重态和三重态激子都可以导致磷光发射，得到很高的磷光效率。改变不同的配体，重金属配合物的发光可以在整个可见光谱范围内调节。这些独特的优点使得重金属配合物发光材料成为电致发光领域的研究热点之一。
Thompson等最早在1999年将重金属铱配合物Ir(ppy)3掺杂到4，4’-N，N’-二咔唑-联苯(CBP)中制成电致磷光器件。这种绿光OLED最高外量子效率达到8.0％(28cd/A)，流明效率达31lm/W，均大大超过电致荧光发光器件，立即引起人们对重金属配合物发光材料的广泛关注。但是，这种基于小分子的电致磷光器件的制备工艺比较复杂，且成本昂贵，需要在高真空下蒸镀多层材料。而基于聚合物主体材料的电致磷光器件则可以用一些简单的制备技术，例如：旋涂、印刷、打印等。迄今为止，文献报道的重金属配合物掺杂的聚合物电致发光器件最大的亮度是8320cd/m2(Ostrowski，J.C.；Robinson，M.R.；Heeger，A.J.；Bazan，G.C.Chem.Commun.2002，7，784.)。
Gong等研究了聚合物电致磷光器件的发光机理(Gong，X.；Robinson，M.R.；Ostrowski，J.C.；Moses，D.；Bazan，G.C.；Heeger，A.J.Adv.Mater.2002，14，581.)，他们认为：从主体材料到磷光掺杂体的能量转移只起到很小的作用，磷光掺杂体直接捕获电子和空穴形成激子是其主要发光机理。因此，发光材料必须有较好的载流子传输性能，使其能够直接捕获电子或空穴。我们将具有良好空穴传输性能的基团咔唑基引入重金属配合物的配体，提高了其空穴传输性能，由其制作成的器件得到了很好的电致发光效应，最大亮度达11845cd/m2，发光效率达18.8cd/A，最大外量子效率达8.5％。并且，通过重金属铱和咔唑的不同位置配位，可以调谐其发光波长，幅度达到84nm。
发明内容
本发明的目的在于提供一种高亮度、高效率、发光可调节的铱配合物电致磷光材料，以及这种重金属铱配合物的配体，和采用这种铱配合物作为磷光掺杂材料的聚合物电致发光器件。
本发明的重金属配合物配体为(C^N)二齿配体，带有咔唑单元，结构通式为
                          R-Cz-Py式中Cz为咔唑单元，Py为吡啶，R为接在咔唑N原子上的烷基，Cz的1、2、3位分别与Py的2位相连。该配体结构式为：
本发明的铱配合物，化学式为Ir(C^N)2(acac)，acac＝乙酰丙酮阴离子。当C^N＝2-吡啶基咔唑时，结构式为：
当C^N＝3-吡啶基咔唑时，结构式为：
本发明的电致发光器件，包括玻璃、附着在玻璃上的导电玻璃衬底层，与导电玻璃衬底层贴合的空穴注入层，与空穴注入层贴合的发光层，与发光层贴合的阴极层，发光层由主体材料和掺杂材料组成，发光层的掺杂材料为如上述的二齿配体的铱配合物，其化学式为Ir(C^N)2(acac)，掺杂比例为2wt％-4wt％，主体材料为聚乙烯基咔唑(PVK)或者聚芴衍生物(PFO)。
本发明的(C^N)二齿配体与已公开的配体相比，通过引入具有良好空穴传输性能的咔唑基团，使其与重金属形成的配合物具有良好的载流子传输性能，提高了器件的亮度和效率。并且可以通过改变取代基的位置，在较宽的范围内调节配合物的发光波长。
本发明的铱配合物具有优异的电致磷光性能，可以作为电致磷光材料，用于电致磷光器件的发光层中。
本发明人发现了具有较高光致发光效率，且能够产生高效电致发光的重金属铱配合物。基于这些配合物的聚合物电致发光器件性能是目前报道的同类型器件中最好的之一，在某些方面优于已公开的类似聚合物电致发光器件。本发明中的一种发绿光的器件最高亮度可达11845坎特拉每平方米，比已公开的同类聚合物发光器件的最高数值8320坎特拉每平方米(Ostrowski，J.C.；Robinson，M.R.；Heeger，A.J.；Bazan，G.C.Chem.Commun.2002，7，784.)提高1.4倍，最大发光效率可达18.8坎特拉每安培，最大外量子效率达8.5％。并且可以调节发光波长达到84nm。
附图说明
图1本发明的电致发光器件结构示意图；
图2本发明的电致发光器件的发射光谱(发光材料为Ir(2-PyC)2(acac)、Ir(3-PyC)2(acac)，2-PyC＝N-正癸基-2-吡啶基咔唑，3-PyC＝N-正癸基-3-吡啶基咔唑，3-PyCE＝N-乙基-3-吡啶基咔唑)。
具体实施方式
下面通过具体实施例对本发明作进一步的说明，但这些具体实施方案不以任何方式限制本发明的保护范围。
本实施方案所用的原料为已知化合物，可在市场上购得，或可用本领域已知的方法合成。
1：配体N-正癸基-2-吡啶基咔唑(2-PyC)，N-正癸基-3-吡啶基咔唑(3-PyC)和N-乙基-3-吡啶基咔唑(3-PyCE)的合成
在Schlenk管中将2-溴吡啶(0.47ml，4.7mmol)溶于7.5ml干燥的THF中，保持在-78℃，15分钟内逐滴加入正丁基锂(2.5M己烷溶液，4.0ml，9.4mmol)，搅拌45分钟后加入无水氯化锌溶液(1.28g，9.4mmol溶于15ml THF)，15分钟内逐渐升至室温，继续搅拌1.5h。然后，加入2-溴-N-正癸基咔唑或3-溴-N-正癸基咔唑(1.79g，4.6mmol)或3-溴-N-乙基咔唑(1.26g，4.6mmol)和Pd(PPh3)4(55.3mg，0.05mmol)的15ml THF溶液，氩气保护下回流16h。冷至室温后，加入10ml氯化铵(2.2g，41mmol)的水溶液，搅拌15分钟后用二氯甲烷萃取，干燥。粗品以氯仿∶石油醚(体积比1∶10)为洗脱剂，硅胶柱层析分离。
N-正癸基-2-吡啶基咔唑：白色固体，收率65％。IR[cm-1]：2917(s)，2845(s)，1589(m)，1449(s)，1327(m)，1344(m).1H NMR(CDCl3，300MHz)δ[ppm]：8.74(dd，J＝4.5，1.2Hz，2H)，8.18(d，J＝7.8Hz，1H)，8.13(dd，J＝8.7，1.5Hz，1H)，7.85(d，J＝8.4Hz，1H)，7.76(m，1H)，7.48(m，3H)，7.21(m，2H)，4.32(t，J＝7.2Hz，2H)，1.93(m，2H)，1.46-1.25(m，14H)，0.89(t，3H).
N-正癸基-3-吡啶基咔唑：油状液体，收率32％。IR[cm-1]：2926(s)，2854(s)，1716(m)，1587(s)，1466(s)，1438(s)，1350(m)，1327(m)，1255(m).1H NMR(CDCl3，300MHz)δ[ppm]：8.74(d，J＝4.5Hz，1H)，8.15(dd，J＝12.6，8.1Hz，3H)，7.86(d，J＝7.86Hz，1H)，7.80(m，2H)，7.45(m，2H)，7.24(m，2H)，4.39(t，J＝7.2Hz，2H)，1.89(m，2H)，1.35-1.23(m，14H)，0.87(t，3H).
2：铱配合物Ir(2-PyC)2(acac)，Ir(3-PyC)2(acac)和Ir(3-PyCE)2(acac)的合成将2-PyC(或3-PyC)(0.55g，1.42mmol)或3-PyCE(0.39g，1.42mmol)溶于乙二醇***∶水(12∶4)的溶液中，然后加入IrCl3·nH2O(0.21g，0.59mmol)，氩气保护，100℃下反应24小时。冷至室温后过滤，滤出物依次用水、乙醇、己烷洗。干燥得环金属铱氯桥二聚体。将此二聚体(0.16g，0.08mmol)，乙酰丙酮(0.24ml)和无水碳酸钠(86mg，0.8mmol)溶于8ml乙二醇***，氩气保护，120℃下反应16小时。过滤洗涤，粗品以二氯甲烷为洗脱剂，硅胶柱层析分离。
Ir(2-PyC)2(acac)：红色固体，收率58％。1H NMR(CDCl3，300MHz)δ[ppm]：8.63(d，J＝5.4Hz，1H)，8.03(d，J＝8.1Hz，1H)，7.80(t，J＝8.1Hz，2H)，7.60(d，J＝7.2Hz，2H)，7.20(m，2H)，6.8(m，2H)，5.23(s，1H)，4.65(t，2H)，1.79(s，6H)，1.31-1.22(m，16H)，0.85(t，3H).Elemental analysis：calculated for C59H69IrN4O2[％]：C 66.95，H 6.57，N 5.29；Found C66.42，H 6.77，N 4.68.MS(FAB)：m/e 1058(M+)。
Ir(3-PyC)2(acac)：黄色固体，收率53％。1H NMR(CDCl3，300MHz)δ[ppm]：8.56(d，J＝5.7Hz，2H)，8.22(s，2H)，7.99(d，J＝8.1Hz，2H)，7.88(d，J＝7.8Hz，2H)，7.74(dd，J＝7.8Hz，7.5Hz，2H)，7.22(m，6H)，6.12(S，2H)，5.25(s，1H)，3.81(t，2H)，1.82(s，6H)，1.26-1.16(m，16H)，0.90(t，3H).Elemental analysis：calculated for C59H69IrN4O2[％]：C 66.95，H 6.57，N5.29；Found C 66.38，H 6.51，N 4.67.MS(FAB)：m/e 1058(M+)。
Ir(3-PyCE)2(acac)：黄色固体，收率50％。1H NMR(CDCl3，300MHz)δ[ppm]：8.59(d，J＝5.7Hz，2H)，8.29(s，2H)，8.04(d，J＝8.1Hz，2H)，7.94(d，J＝7.8Hz，2H)，7.76(dd，J＝7.8Hz，7.5Hz，2H)，7.25(m，6H)，6.17(s，2H)，5.28(d，J＝8.4Hz，1H)，3.90(t，2H)，1.82(s，6H)。
电致发光器件可按本领域已知方法制做，如按参考文献(Adv.Mater.2004，16，537.)公开的方法制作。具体方法为：再高真空条件下，在经过清洗的导电玻璃(ITO)衬底上依次旋涂40nm PEDOT：PSS，80nm(PVK+PBD40％)：铱配合物(或PFO：铱配合物)，4nm钡，120nm铝。
3：器件的制作
如图1所示，本发明的铱配合物作为发光层的器件可包括玻璃1、导电玻璃(ITO)衬底层2，空穴注入层3(聚乙烯二氧噻吩：聚磺酸苯乙烯(PEDOT：PSS))，发光层4(铱配合物掺杂聚乙烯咔唑：2-(4-联苯基)-5-(4-叔丁基苯基)-1，3，4-噁二唑(PVK：PBD)或铱配合物掺杂聚芴衍生物(PFO))，阴极层5(钡、铝)。
电致发光器件可按本领域已知方法制做，如按参考文献(Adv.Mater.2004，16，537.)公开的方法制作。具体方法为：在高真空条件下，在经过清洗的导电玻璃(ITO)衬底上依次旋涂40nm PEDOT：PSS，80nm(PVK+PBD40％)：铱配合物(或PFO：铱配合物)，通过蒸镀引入4nm钡，120nm铝作为阴极。
用该方法制得如图1的器件，制得的各种器件的结构如下：
器件一：ITO/PEDOT(40nm)/(PVK+PBD40％)：Ir(2-PyC)2(acac)2％(80nm)/Ba(4nm)/Al(120nm)
器件二：ITO/PEDOT(40nm)/PVK(40nm)/PFO：Ir(2-PyC)2(acac)4％(80nm)/Ba(4nm)/Al(120nm)
器件三：ITO/PEDOT(40nm)/(PVK+PBD40％)：Ir(3-PyC)2(acac)4％(80nm)/Ba(4nm)/Al(120nm)
器件四：ITO/PEDOT(40nm)/PVK(40nm)/PFO：Ir(3-PyC)2(acac)4％(80nm)/Ba(4nm)/Al(120nm)
测量器件性能及电致发光光谱时，ITO电极总是与正极相连。电致发光光谱是在CCD光谱仪上测定(见图2)，电流(I)-电压(V)-亮度(L)数据在Keithley 236 Source MeasurementUnit上测定，并由硅光电二极管校正。发光效率(cd/A)由硅光电二极管测定，并由PR-705SpectraScan Spectrophotometer校正。外量子效率由积分球(IS-080，Labsphere)测定。
器件的性能数据见下表：
器件   最高亮度cd/m2 最高发光效率cd/A 最高外量子效率％   发光波长nm 发光光谱
    器件一器件二器件三器件四文献最高值     340920901184593678320     5.643.2718.7716.3036     5.843.398.517.3810     608608524524546     见图2见图2见图2见图2
所制得的器件二与文献(Chem.Commun.2002，7，784.)相比，最高亮度可达11845坎特拉每平方米，比文献值提高1.4倍，最大发光效率可达18.8坎特拉每安培，最大外量子效率达8.51％，都接近文献值。由Ir(3-PyCE)2(acac)制作的同类型电致磷光器件也取得了很好的效果。因此，与其它铱配合物电致发光材料及器件相比，本发明具有更高的亮度和较好的电致发光效率，并且，本发明的配体可以在很大范围的调节配合物的发光波长，为开发新的蓝光电致发光材料提供了新的途径，有利于制备全彩显示器。

Claims (5)

1.一种二齿配体，其结构为：
式中R为烷基。
2.如权利要求1所述二齿配体的铱配合物，其结构为：
或
式中R为烷基。
3.一种铱配合物的电致发光器件，包括玻璃、附着在玻璃上的导电玻璃衬底层，与导电玻璃衬底层贴合的空穴注入层，与空穴注入层贴合的发光层，与发光层贴合的阴极层，发光层由主体材料和掺杂材料组成，其特征在于：发光层的掺杂材料为如权利要求2所述二齿配体的铱配合物。
4.如权利要求4所述的铱配合物电致发光器件，其特征在于：二齿配体的铱配合物的掺杂比例为2wt％-4wt％。
5.如权利要求4或5所述的铱配合物电致发光器件，其特征在于：主体材料为聚乙烯基咔唑或聚芴衍生物。
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