CN100509827C - 电致发光材料 - Google Patents

电致发光材料 Download PDF

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CN100509827C
CN100509827C CNB038099225A CN03809922A CN100509827C CN 100509827 C CN100509827 C CN 100509827C CN B038099225 A CNB038099225 A CN B038099225A CN 03809922 A CN03809922 A CN 03809922A CN 100509827 C CN100509827 C CN 100509827C
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Abstract

采用衍生于四齿状ONNO型配体和第10族金属的高发光、热稳定抗湿的发光材料被作为有机发光器件的搀杂剂。

Description

电致发光材料
发明领域
本发明涉及发光材料，它可通过真空沉积方法沉积为薄层，而且可用于有机发光器件(OLED)中作为有效搀杂剂。
发明背景
过去二十多年来，发光二极管(LED)的进展主要集中于无机型，因为早期开发的有机发光器件(OLED)制造低劣和包装欠佳，寿命较短。而今市场一般可提供砷化镓基的LED，其效能在某些光谱区超过了常规滤波荧光灯(filtered fluorescent lamps)。但是，在显示技术发光材料的发展方面，对于大面积集中显示器，无机半导体材料是不适应的。
Pope等人六十年代在纽约大学提出了基于蒽材料的有机电致发光(J Chem.Phys.38，2042，1963))。自从CW Tang等人在科达公司(Kodak)(Appl.Phys.Lert.51，913，(1987))发现了三(8-hydroxyquinolato)铝(Alq3)基的薄膜器件后，已取得了许多进展。这些进展主要贡献于连续发现新的和改良的电致发光材料。从小荧光分子至共轭聚合物，许多OLED均已表明其呈现亮度充分、效能显著，使用寿命长和颜色渲染理想。
含金属络合物的有机发光器件因其独特的化学和电子学特性是特别有意义的。某些载有重金属的化合物对于OLED因内量子效率高而显示出潜在的优点。通常利用荧光材料作为发射基质的搀杂剂。单激子(最大理论内量子效率＝25％)在孔眼和电子再结合后形成，通过Foster机理(US 6,310,360)经偶极-偶极相互作用而电致发光。然而对于重金属络合物，强自旋轨道耦合可导致单独-三重态混合，这在OLED中可导致高效率的电致磷光(理论内量子效率最高100％(Nature(自然)，395，151，(1998)；Synthetlc Metals(合成金属)，93，245，(1998)；Appl.Phys.Lert(应用物理学通讯)77；904，(2000))。
但是，某些发磷光材料存在本征缺点，诸如，由于寿命过长及在高掺杂水平下由强分子间相互作用而引起的三重-三重态湮灭和浓缩抑制而使发射中心饱和(Phys.Rev(物理学评论)B.60，14422，(1999))。
例如，在有机发光器件中四齿甲亚胺-锌络合物已被用作蓝光发射极，它呈现最大发光率仅约1000cd/m2(Jpn.J.Appl.Phys.(日本应用物理学杂志)，32，1511(1993)；US 5,432，014)。
甲亚胺-铝/镓络合物已应用于OLED作为发射材料。在10V下含甲亚胺-镓络合物的器件的电流密度为1mA/cm2，电致发光是兰绿色的(US6,316,130)。
因此，最好是研发一些发射搀杂剂材料，能使OLED中基质与搀杂剂之间进行有效能量传递，同时促使甚至在十分高的掺杂浓度下也几乎没有自抑制(self-quenching)。
发明综述
在其实施方案中本发明实施例的目的包括：
本发明主要目的在于制备掺入新发光材料的有机发光器件(OLED)。这些器件接通电压低，发光率和效能高。
本发明一个目的在于提供热稳定的抗湿的金属螯合材料，使能通过汽相沉积的方法沉积为已知厚度的薄层。
此外，本发明涉及高发光搀杂剂，它用于发光器件中可浓度低。
衍生于四齿ONNO型配体和一种第10族金属(包括铂)的新发光材料，是按化学式I和II的说明制备的：
Figure C03809922D00051
其中M表示第10族金属(包括铂)和R1-R14是各单独选自氢、卤素、烷基、取代的烷基、芳烃基、取代的芳基、带有选自卤素、低级烷基和被认可的供体和受体基团的取代基。
本发明实施方案包括但不局限于包含用于产生电致发光的杂原子结构的OLED，它含有阳极(ITO玻璃物质)、孔眼传递层(NPS(α-萘基苯基联苯基胺))、基质发射层[基质材料(铍双(2-(2′-羟苯基)吡啶)(Bepp2))，具有不同浓度的如这里化学式I和II所说明的搀杂剂]、电荷迁移层(氟化锂)和阴极(铝金属)。
在这里，OLED中作为有效搀杂剂的优选实施方案是：
Figure C03809922D00061
本发明提供了一些新型材料作为电致发光器件中发射搀杂剂。本发明包括对这些新络合物的合成方法和其作为发光材料的应用。本发明器件能应用于场显示器、光发射极、信号灯的显示板、或液晶显示屏的光源。
附图说明
图1为络合物1b及2b在CH2Cl2中的吸收光谱；
图2为络合物1b在CH2Cl2中和作为薄膜在298K下的发射光谱；
图3为络合物2b在CH2Cl2中和作为薄膜在298K下的发射光谱
图4为络合物1b和2b在氮和空气条件下的TGA热谱图；
图5为本发明OLED的原理框图；
图6a为含络合物1b(掺入量0.3重量％)的器件A电致发光光谱；
图6b为含络合物1b(掺入0.3重量％)的器件A的电流密度-电压-发光率曲线；
图7a为含络合物1b(掺入量1.0重量％)的器件B电致发光光谱；
图7b为含络合物1b(掺入量1.0重量％)的器件B的电流密度-电压-发光率曲线；
图8为含络合物1b(掺入量2.0重量％)的器件C电致发光光谱。
发明详述
本发明一般是与这些新发光材料的合成、光谱特征、磷光、发光特性和其在OLED中的应用相关的。提出这些实施例是为了帮助对本发明的理解，而非试图也不应以任何形式将其视为对本发明的限制，如此后权利要求中所规定的那些。
所给出的实施例说明配体1a和2a和铂络合物1b和2b的合成方法。四齿ONNO型配体1a和2a是按照改进的文献方法制备的(J Chem.Soc.，Perkin Trans.2，863，(1998))。制备ONNO型配体的另一实例已经报导过(见US6,177,419)。
实施例1
1a的合成
Figure C03809922D00071
回流6，6’-双(2-甲氧苯基)-4，4’-双(叔丁基)-2，2’-联吡啶(1克)在氢溴酸(47％，20毫升)中的一种混合物12小时。将其冷却至室温，在室温下用饱和Na2CO3溶液对其中和。用氯仿萃取该有机产物，用去离子水(50毫升x 2)洗涤该萃取液，用无水Na2SO4干燥，脱除溶剂获得一种固体残留物。用从甲醇/二氯甲烷溶液重结晶的方法，获得1a的结晶产物。
                 EI-MS(m/z)：452[M]+.1H NMR(CDCl3，δ，ppm)：14.45(2H，s，OH)，8.16(2H，d，J＝1.4Hz，ArH)，7.97(2H，d，J＝1.3Hz，ArH)，7.90(2H，dd，J＝8.0Hz，J＝1.4Hz，ArH)，7.34(2H，td，J＝8.4Hz，J＝1.5Hz，ArH)，7.07(2H，dd，J＝8.2Hz，J＝16Hz，ArH)，6.96(2H，td，J＝8.1Hz，J＝1.2Hz，ArH)，1.47(18H，s，tBu).13C NMR(CDCl3，δ，ppm)：163.3，159.7，157.5，152.2，131.5，126.5，119.2，118.9，118.4，116.4，35.6，30.6.
实施例2
1b的合成
Figure C03809922D00081
现描述金属络合物1b的合成方法。搅拌NaOMe(0.014克，0.25毫摩尔)和配体1a(0.113，0，25毫摩尔)在甲醇(20毫升)中的混合物2小时。将Pt(CH3CN)2Cl2(0.25毫摩尔)的乙腈溶液(20毫升)加至该甲醇悬浮液中，对其回流24小时。过滤所得悬浮液，并将其浓缩至约5毫升。添加二乙醚后获得一种褐黄色固体。将二乙醚扩散进入二氯甲烷溶液中使粗制品重结晶，产生黄色晶体。
    　　　　　　　　　　　　　　FAB-MS(m/z)：645[M]+，1292(2M++2)，1938(3M++3).1H NMR(CDCl3，δ，ppm)：8.32(d，2H，J＝1.41Hz ArH)，8.01(d，2H，J＝7.25Hz，ArH)，7.85(d，2H，J＝1.68Hz，ArH)，7.48(dd，2H，J＝7.38Hz，J＝1.13Hz，ArH)，7.38(td，2H，J＝5.35，1.61Hz，ArH)，6.79(td，2H，J＝5.40，1.35Hz，ArH)，1.54(s，18H，tBu).13C NMR(CDCl3，δ，ppm)：162.745，159.105，155.291，149.851，131.269，128.005，124.060，120.465，120.402，116.302，116.14g，30.402，29.715.FTIR(KBr，cm-1)：3086w，2953m，1612w，1528s，1351s，1034m，885w，723m.
实施例3
2a的合成
Figure C03809922D00082
在装有回流冷凝器的100毫升圆底烧瓶中，混合2，9-双(2-甲氧苯基)-4，7-二苯基-1，10-菲咯啉(磨得很细的，2克，3.7毫摩尔)和吡啶盐酸盐(4.23克，37毫摩尔)。在氮气流下加热该混合物至210℃36小时。冷却后，加入水(30毫升)并用氯仿(3x30毫升)萃取。将合并后的有机萃取液用饱和碳酸氢钠溶液(5x30毫升)和水(3 x 30毫升)洗涤，用无水硫酸镁干燥洗涤后样品，并加意蒸发，得到一种嫩黄色固体。在硅胶上利用正己烷：二氯甲烷(1∶2)作为洗脱液，进行层析，得到0.99克的一种黄色固体。
   FAB-MS(m/z)：517[M+H]+.1H NMR(300MHz，CDCl3，δ，ppm)：14.69(2H，s，OH)，8.52(2H，s，ArH)，8.41(2H，dd，J＝8.0，1.3Hz，ArH)，7.90(2H，s，ArH)，7.71(4H，d，J＝7.4Hz)，7.64(6H，m，ArH)，7，43(2H，td，J＝7.7，1.5Hz，ArH)，7.10(2H，dd，J＝7.4Hz，1.3Hz，ArH)，7.04(2H，td，J＝7.5，1.3Hz，ArH).13C NMR(600MHz，CDCl3)：δ＝160.5，157.7，150.3，142.8，137.8，132.2，129.6，128.9，128.8，127.1，125.7，123.7，120.6，119.4，119.2，118.9.
实施例4
2b的合成
Figure C03809922D00091
回流在冰醋酸(10毫升)中的K2PtCl4(0.08克，0.19毫摩尔)和锌(0.1克，0.19摩尔)2天。冷却后，过滤收集所得悬浮液，用乙酸和水连续地洗涤，然后在真空下干燥，得到一种褐色固体。用层析法在硅胶吸附塔内用二氯甲烷作为洗脱液提纯该粗制品。缓慢蒸发二氯甲烷溶液，重结晶该产物，得到红色晶粒：
                             FAB-MS：m/z＝710[M+H]+.1H NMR(270MHz，DMSO-d6)8.81(2H，s，ArH)，8.56(2H，d，J＝8.9Hz，ArH)，8.01(2H，s，ArH)，7.86(4Hm，ArH)，7.71(6H，dd，J＝4.9，2.0Hz，ArH)，7.44(2H，t，J＝7.4Hz，ArH)，7.24(2H，d，J＝8.2Hz，ArH)，6.80(2H，t，J＝7.6Hz，ArH).
按照本发明的铂络合物1b和2b的光谱特征示于表1中。(由图1)观察到络合物1b强吸收频带在250-350纳米(ε＝38400-17500dm3mot-1cm-1)，中等强吸收频带在λ 398纳米(ε＝10800dm3mot-1cm-1)。另外，在约480纳米(2800dm3mot-1cm-1)可看到有一宽吸收频带。在CH2Cl2中，对于络合物2b(图1)观察到在291-375纳米(ε＝39200-24700dm3mot-1cm-1)有若干电子振动跃迁和在504纳米(ε＝7200dm3mot-1cm-1)观察到有一个宽频带。
表1 CH2Cl2中1b和2b的紫外/可见光吸收数据
 
络合物 λ<sub>max</sub>/nm(ε/10<sup>4</sup>xdm<sup>3</sup>mot<sup>-1</sup>cm<sup>-1</sup>)
1b 255(3.80)，315(1.75)，400(0.82)，480(0.25)，505(0.22)
2b 291(3.92)，315(3.40)，325(3.23)，352(2.58)，375(2.47)，420(0.52)，488(0.67)，504(0.72)                                              
对在溶液中和作为薄膜的铂络合物1b和2b的光致发光(PL)概述于表2中。在图2中，在CH2Cl2中和作为薄膜的络合物1b在595和599纳米处分别观察到298K的无定形发射。对在溶液中和作为薄膜的络合物2b的PL特性示于图3。与溶液中的相比，在薄膜中2b的最大发射被移动到1704cm-1。同时，络合物1b和2b在CH2Cl2中呈现寿命1.9和5.3微秒，荧光量子效率分别为0.1和0.6(用Ru(bpy)3Cl2作为参比标准)。
表2 在溶液中和作为薄膜的络合物1b和2b的PL特性
 
络合物(测定介质/温度) 发射(最大/纳米) 寿命(微秒) 量子效率
1b(CH<sub>2</sub>Cl<sub>2</sub>/298K) 595 1.9 0.1
1b(薄膜/298K) 599 / /
1b(CH<sub>2</sub>Cl<sub>2</sub>/298K) 586 5.3 0.6
1b(薄膜/298K) 651 / /
浓度：＝1 x 10-5mol dm-3
络合物1b和2b的TGA热谱示于图4。两络合物在氮和空气中在加热速率15℃/分下表现热稳定性高。络合物2b在氮气中稳定最高达536℃和在空气中最高达379℃。在氮气中1b的起始(on-set)温度达438℃，而在空气中为382℃。这些观察表明这些发光材料可被升华并且能在OLED制备的真空沉积条件下是稳定的。
图5图解说明按照本发明的一种电致发光器件。作为本发明的实施例，制备了一些OLED，其结构为ITO/NPB(α-萘基苯基联苯基胺)(500
Figure C03809922D0011135600QIETU
)/[0.3重量％(器件A)、1重量％(器件B)、或2重量％(器件C)的络合物1b]：Bepp2(400
Figure C03809922D0011135600QIETU
)/LiF(15
Figure C03809922D0011135600QIETU
)/A1(2000
Figure C03809922D0011135600QIETU
)。器件A(0.3重量％的1b)的制备如下。
实施例5
器件A装配如下：在玻璃底物上薄层电阻20Ω/平方的氧化铟锡(ITO)电极、厚度500
Figure C03809922D0011135600QIETU
的孔眼传递材料NPB(α-萘基苯基联苯基胺)、由0.3重量％络合物1b和兰色荧光材料Bepp2(铍双(2-(2’-羟苯基)吡啶)制成的其厚度400
Figure C03809922D0011135600QIETU
的发射层、厚度15
Figure C03809922D0011135600QIETU
的增强电荷传递层LiF和厚度2000
Figure C03809922D0011135600QIETU
的铝层。将这些金属和各有机层在不同真空淀积过程间不间断5 x 10-6毫巴的真空下依次层压。以每秒2或5
Figure C03809922D0011135600QIETU
的速率沉积这些层。按对阴极和阳极重叠面积的规定该器件的发射面积是3 x 3平方厘米。用有机溶剂(丙酮-异丙醇-甲醇)、去离子水，接着用紫外线-臭氧净化器清洁该ITO镀膜玻璃滑片。用分光光度计和计算机控制的直流电源，在室温下分别测定这些器件的EL光谱和电流密度-电压-发光率的特征。
对于这些实施例，当调节络合物1b的掺入浓度从2至0.3重量％时，该器件的外部效率增大。对具体实施例进一步说明如下：
实施例6
对于络合物1b掺入量为0.3重量％的器件A，其性能示于图6a和6b中。当在正偏压驱动器件时，观察到在453纳米和540纳米下有二个强EL发射。也显示了器件A的电流密度-电压-发光率特性曲线。接通电压为约6-7V。在发光率2849cd/m2下，该器件最大效率是4.1cd/A。在10V驱动电压下，获得最大发光率为9325cd/m2。器件A的EL显色是黄色(CIE座标：x＝0.33，y＝0.47)。
实施例7
对于络合物1b掺入量为1.0重量％的器件B，其性能示于图7a和7b中。该器件在546纳米呈现一个强EL发射峰，在457纳米呈现一个弱发射。器件B的接通电压为约6-7V。在驱动电压9.5V下，其效率在发光率3927cd/m2下是1.9cd/A和最大发光率为6563cd/m2。器件B的EL显色是黄色(CIE座标：x＝0.39，y＝0.54)。
实施例8
实施例8
对于络合物1b掺入量为2.0重量％的器件C，其在548纳米呈现一个强EL发射峰，和在约450纳米处呈现一个极弱发射(图8)；EL效率检测为1.5cd/A。在驱动电压12V下，观察到发光率为6450cd/m2。器件C的EL显色是黄色(CIE座标：x＝042，y＝0.56)。
一般据报导，掺入量高于5％，可实现在有机或聚合发光器件中的搀杂剂发射。在本发明中，OLED实际显示，当掺入量约2％时，络合物1b就完全发射，当减小络合物掺入量从2.0至0.3重量％时，器件效率从1.5增大至4，1cd/A。

Claims (10)

1.用于产生电致发光的含杂原子结构的有机发光器件中的一层发射层，包括至少一种基质材料和一种发射分子，以一种搀杂剂存在于所述基质材料中，其中所述发射分子选自载有一种四齿ONNO型配体的金属络合物，NN是2，2′-联吡啶或取代的2，2′-联吡啶或1，10-菲咯啉或取代的1，10-菲咯啉，其中的取代基选自氢、卤素、烷基和芳基。
2.按照权利要求1的发射层，其中所述金属络合物的金属选自第10族。
3.按照权利要求1的发射层，其中所述发射分子可以具有以式I或II表示的化学结构：
Figure C03809922C00021
其中M表示第10族金属，和R1-R14各单独选自氢、卤素、烷基和芳基。
4.按照权利要求3的发射层，其中所述发射分子是作为搀杂剂出现于所述基质材料中的，按基质材料重量计，存在量为0.3-2.0％重量。
5.按照权利要求3的发射层，它产生黄色电致发光。
6.一种用于对包括按照权利要求4发射层的有机发光器件所发射颜色进行调变的方法。
7.按照权利要求3的发射层，其中所述基质材料是铍双(2-(2′-羟苯基)吡啶。
8.按照权利要求3的发射层，其中所述基质材料和所述发射分子可以通过升华或真空沉积或汽相沉积或旋涂或其它方法被沉积为一薄层。
9.式I所表示的发射分子，其中R1-R5、R7-R8和R10-R14基团是质子原子、R6和R9基团是叔丁基基团、M是铂、即：
Figure C03809922C00031
10.式II所表示的发射分子，其中R1-R5、R7-R8和R10-R14基团是质子原子、R6和R9基团是苯基，M是铂，即：
Figure C03809922C00032
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