CN106431937B - 一种有机发光材料及其应用 - Google Patents

一种有机发光材料及其应用 Download PDF

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CN106431937B
CN106431937B CN201610832724.1A CN201610832724A CN106431937B CN 106431937 B CN106431937 B CN 106431937B CN 201610832724 A CN201610832724 A CN 201610832724A CN 106431937 B CN106431937 B CN 106431937B
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叶中华
李崇
张兆超
徐凯
张小庆
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Jiangsu Sunera Technology Co Ltd
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Abstract

本发明公开了一种有机发光材料及其应用，该发光材料的结构式如通式(1)所示。该种材料具有良好的荧光量子效率和电致发光效率，具有良好的热稳定性，因此该类材料可作为有机电致发光器件中的发光层掺杂材料使用。

Description

一种有机发光材料及其应用
技术领域
本发明涉及半导体技术领域，尤其是涉及一种荧光化合物的合成，以及作为发光层掺杂材料在有机发光二极管上的应用。
背景技术
有机电致发光(OLED:Organic Light Emission Diodes)器件技术既可以用来制造新型显示产品，也可以用于制作新型照明产品，有望替代现有的液晶显示和荧光灯照明，应用前景十分广泛。
当前，OLED显示技术已经在智能手机，平板电脑等领域获得应用，进一步还将向电视等大尺寸应用领域扩展。但是，和实际的产品应用要求相比，OLED器件的发光效率，使用寿命等性能还需要进一步提升。
OLED发光器件犹如三明治的结构，包括电极材料膜层，以及夹在不同电极膜层之间的有机功能材料，各种不同功能材料根据用途相互叠加在一起共同组成OLED发光器件。作为电流器件，当对OLED发光器件的两端电极施加电压，并通过电场作用有机层功能材料膜层中正负电荷，正负电荷进一步在发光层中复合，即产生OLED电致发光。
对于OLED发光器件提高性能的研究包括：降低器件的驱动电压，提高器件的发光效率，提高器件的使用寿命等。为了实现OLED器件的性能的不断提升，不但需要从OLED器件结构和制作工艺的创新，更需要OLED光电功能材料不断研究和创新，创制出更高性能OLED的功能材料。
应用于OLED器件的OLED光电功能材料从用途上可划分为两大类，即电荷注入传输材料和发光材料，进一步，还可将电荷注入传输材料分为电子注入传输材料和空穴注入传输材料，还可以将发光材料分为主体发光材料和掺杂材料。为了制作高性能的OLED发光器件，要求各种有机功能材料具备良好的光电特性，譬如，作为电荷传输材料，要求具有良好的载流子迁移率，高玻璃化转化温度等，作为发光层的材料要求材料具有良好的荧光量子效率、材料蒸镀稳定性、适当的HOMO/LUMO能阶等。
构成OLED器件的OLED光电功能材料膜层至少包括两层以上结构，产业上应用的OLED器件结构，则包括空穴注入层、空穴传输层、发光层、电子注入层等多种膜层，也就是说应用于OLED器件的光电功能材料至少包含空穴注入材料，空穴传输材料，发光材料，电子注入材料等，材料类型和搭配形式具有丰富性和多样性的特点。另外，对于不同结构的OLED器件搭配而言，所使用的光电功能材料具有较强的选择性，相同的材料在不同结构器件中的性能表现，也可能完全迥异。
目前，荧光材料研究方面已经取得了长足的发展，能够满足产业化的需求；但是其效率、寿命方面依然存在不足，不易达到全彩RGB的要求。因此，针对当前OLED显示照明产业的实际需求而言，荧光材料的发展还远远不够，落后于面板制造企业的要求，作为材料企业开发更高性能的有机功能荧光材料显得尤为重要。
发明内容
针对现有技术存在的上述问题，本申请人提供了一种有机发光材料及其应用。本发明化合物作为发光层主体材料或者掺杂材料制作出的OLED器件具有良好的外量子效率、材料稳定性以及色纯度，能够满足面板制造企业的要求。
本发明的技术方案如下：
本申请人提供了一种有机电致发光材料，所述材料的结构如通式(1)所示：
Figure BDA0001116294210000021
通式(1)中，R1表示为取代或者为取代的苯基，并且与C1-C2、C2-C3、或C3-C4键结成环；当R1表示为取代的苯基时，其取代基为取代或未取代的芳胺基、或者取代或未取代的含氮杂芳基；
R3、R4分别独立的表示为氢、碳原子数1-6的烷基、苯基；或者R3、R4通过键结形成碳原子数为10-16的芳基环；
R2表示为通式(4)、(5)、(6)中的一种：
Figure BDA0001116294210000031
a选自
Figure BDA0001116294210000032
中的一种；
a与C5-C6键、C6-C7键、或C7-C8键连接；
X1、X2、X3分别独立的表示为氧原子、硫原子、C1-10直链或支链烷基取代的亚烷基、芳基取代的亚烷基、烷基或芳基取代的叔胺基中的一种；
X4、X5分别独立的表示为氢、碳原子数1-6的烷基、苯基；或者X4、X5通过键结的形成碳原子数为10-16的芳基环；
R5独立地表示为取代或未取代的芳胺基、取代或者未取代的含氮杂芳基中的一种。
优选的，所述化合物材料选自通式(1a)-(3a)的任一种：
Figure BDA0001116294210000033
其中，通式(1a)-(3a)中的Ra分别独立的表示为取代或未取代的芳胺基、取代或未取代的含氮杂芳基。
优选的，所述Ra、R5分别独立的采用通式(7)或(8)表示：
Figure BDA0001116294210000041
通式(7)、(8)中，X6为氧原子、硫原子、C1-10直链或支链烷基取代的亚烷基、芳基取代的亚烷基、烷基或芳基取代的叔胺基中的一种；
R6、R7分别独立的表示为氢、碳原子数1-6的烷基、芳基、或芳胺基；且R6、R7至少有一个表示为芳胺基。
优选的，所述Ra、R5分别独立的采用通式(9)表示：
Figure BDA0001116294210000042
其中，R8、R9分别独立的表示为芳基、或杂芳基。
优选的，R6、R7、R8、R9分别独立的表示为取代或未取代的苯基、吡啶基、二联苯基、三联苯基、萘基、蒽基、菲基、三嗪基、嘧啶基、喹啉基、二苯并呋喃基、二苯并噻吩基、9,9-二甲基芴基、或9,9-二苯基芴基中的一种。
优选的，所述发光材料的具体结构为：
Figure BDA0001116294210000043
Figure BDA0001116294210000051
Figure BDA0001116294210000061
Figure BDA0001116294210000071
Figure BDA0001116294210000081
Figure BDA0001116294210000091
Figure BDA0001116294210000101
Figure BDA0001116294210000111
Figure BDA0001116294210000121
中的任一种。
本申请人还提供了一种含有所述有机电致发光材料的有机电致发光器件，所述材料作为发光层掺杂材料应用于有机电致发光二极管。
所述有机电致发光材料作为发光层掺杂材料时，所述有机电致发光器件具有下列通式(a)表示的化合物作为主体材料：
Figure BDA0001116294210000122
通式(a)中，R1-R4、R7-R10分别独立的表示为氢原子、C1-C10的烷基或环烷基、取代或者未取代的芳香基、杂芳基；
其中n，m分别独立的选取0-3的整数，但不等同时为0；
R5、R6分别独立的表示取代或者未取代的芳香基或者杂芳基。
本发明有益的技术效果在于：
本发明所述化合物可应用于OLED发光器件制作，并且可以获得良好的器件表现，所述化合物作为OLED发光器件的独立的发光层材料、或者发光层掺杂材料使用时，器件的发光效率，功率效率和外量子效率均得到很大改善；器件色纯度得到明显改善，器件寿命得到提升。本发明所述化合物在OLED发光器件中具有良好的应用效果，具有良好的产业化前景。
本发明以二苯并庚烯上的C-C键与芴连接所形成的结构为核心，并且通过胺基上不同的取代基对化合物进行修饰，该类结构的分子具有较强的空间立体作用，能够有效降低分子间的聚集效应，抑制材料的结晶程度，该类材料运用于有机发光二极管中，可以有效提高器件效率和寿命。
附图说明
图1为本发明发光材料制成的OLED器件的示意图。
图中：1、透明基板层，2、ITO阳极层，3、空穴注入层，4、空穴传输层，5、发光层，6、电子传输层，7、电子注入层，8、阴极反射电极层。
具体实施方式
为了更加清楚的了解本发明的技术手段和实用目的，通过列举实施例和比较例，同时辅以图片加以说明。
实施例1(化合物06)
现提供该化合物的具体合成路线：
Figure BDA0001116294210000131
250ml的四口瓶，氮气保护下，加入0.01mol中间体A，0.011mol二苯胺，0.03mol叔丁醇钠，1×10-4mol Pd2(dba)3，1×10-4mol三叔丁基膦，150ml甲苯，加热回流20小时，反应完全；自然冷却，过滤，滤液旋蒸，过硅胶柱，用甲苯:乙醇＝1:2(体积比)混合溶剂打浆，重结晶后白色固体，纯度(HPLC)为98.1％，收率62.2％。
元素分析结构(分子式C52H37N)：理论值C,92.41；H,5.52；N,2.07
测试值：C,92.39；H,5.57；N,2.04
实施例2(化合物11)
现提供该化合物的具体合成路线：
Figure BDA0001116294210000141
250ml的四口瓶，氮气保护下，加入0.01mol中间体B，0.011mol双(4-叔丁基苯基)胺，0.03mol叔丁醇钠，1×10-4mol Pd2(dba)3，1×10-4mol三叔丁基膦，150ml甲苯，加热回流20小时，反应完全；自然冷却，过滤，滤液旋蒸，过硅胶柱，用甲苯:乙醇＝1:3(体积比)混合溶剂打浆，重结晶后白色固体，纯度(HPLC)为97.8％，收率60.4％。
元素分析结构(分子式C50H51N)：理论值C,90.18；H,7.72；N,2.10
测试值：C,89.94；H,7.76；N,2.30
实施例3(化合物15)
现提供该化合物的具体合成路线：
Figure BDA0001116294210000142
250ml的四口瓶，氮气保护下，加入0.01mol中间体C，0.025mol双(4-叔丁基苯基)胺，0.03mol叔丁醇钠，1×10-4mol Pd2(dba)3，1×10-4mol三叔丁基膦，150ml甲苯，加热回流20小时，反应完全；自然冷却，过滤，滤液旋蒸，过硅胶柱，用甲苯:乙醇＝1:2.5(体积比)混合溶剂打浆，重结晶后白色固体，纯度(HPLC)为98.3％，收率53.1％。
元素分析结构(分子式C69H55N2O)：理论值C,89.19；H,6.07；N,3.01；O,1.72
测试值：C,89.24；H,6.10；N,2.98；O,1.68
实施例4(化合物25)
现提供该化合物的具体合成路线：
Figure BDA0001116294210000143
250ml的四口瓶，氮气保护下，加入0.01mol中间体D，0.025mol二苯胺，0.03mol叔丁醇钠，1×10-4mol Pd2(dba)3，1×10-4mol三叔丁基膦，150ml甲苯，加热回流20小时，反应完全；自然冷却，过滤，滤液旋蒸，过硅胶柱，用甲苯:乙醇＝2:1(体积比)混合溶剂打浆，重结晶后白色固体，纯度(HPLC)为97.6％，收率59.2％。
元素分析结构(分子式C57H43N3)：理论值C,88.91；H,5.63；N,5.46
测试值：C,88.87；H,5.57；N,5.56
实施例5(化合物28)
现提供该化合物的具体合成路线：
Figure BDA0001116294210000151
250ml的四口瓶，氮气保护下，加入0.01mol中间体E，0.025mol化合物a，0.03mol叔丁醇钠，1×10-4mol Pd2(dba)3，1×10-4mol三叔丁基膦，150ml甲苯，加热回流20小时，反应完全；自然冷却，过滤，滤液旋蒸，过硅胶柱，用甲苯:乙醇＝1:3(体积比)混合溶剂打浆，重结晶后白色固体，纯度(HPLC)为97.9％，收率59.8％。
元素分析结构(分子式C74H68N2O2)：理论值C,87.36；H,6.74；N,2.75；O,3.15；
测试值：C,87.31；H,6.80；N,2.80；O,3.09。
实施例6(化合物33)
现提供该化合物的具体合成路线：
Figure BDA0001116294210000152
250ml的四口瓶，氮气保护下，加入0.01mol中间体F，0.011mol(3-二苯基胺基)咔唑，0.03mol叔丁醇钠，1×10-4mol Pd2(dba)3，1×10-4mol三叔丁基膦，150ml甲苯，加热回流20小时，反应完全；自然冷却，过滤，滤液旋蒸，过硅胶柱，用甲苯:乙醇＝1:1(体积比)混合溶剂打浆，重结晶后白色固体，纯度(HPLC)为97.6％，收率55.4％。
元素分析结构(分子式C64H44N2)：理论值C,91.40；H,5.27；N,3.33
测试值：C,91.28；H,5.31；N,3.41
实施例7(化合物38)
现提供该化合物的具体合成路线：
Figure BDA0001116294210000161
基)咔唑，0.03mol叔丁醇钠，1×10-4mol Pd2(dba)3，1×10-4mol三叔丁基膦，150ml甲苯，加热回流20小时，反应完全；自然冷却，过滤，滤液旋蒸，过硅胶柱，用甲苯:乙醇＝1:2(体积比)混合溶剂打浆，重结晶后白色固体，纯度(HPLC)为97.9％，收率54.6％。
元素分析结构(分子式C76H55N3)：理论值C,90.35；H,5.49；N,4.16
测试值：C,90.40；H,5.54；N,4.06
实施例8(化合物57)
现提供该化合物的具体合成路线：
Figure BDA0001116294210000162
250ml的四口瓶，氮气保护下，加入0.01mol中间体H，0.011mol(2-二苯胺基)吖啶，0.03mol叔丁醇钠，1×10-4mol Pd2(dba)3，1×10-4mol三叔丁基膦，150ml甲苯，加热回流20小时，反应完全；自然冷却，过滤，滤液旋蒸，过硅胶柱，用甲苯:乙醇＝1:2(体积比)混合溶剂打浆，重结晶后白色固体，纯度(HPLC)为98.4％，收率52.6％。
元素分析结构(分子式C64H44N2O)：理论值C,89.69；H,5.17；N,3.27；O,1.87；
测试值：C,89.72；H,5.20；N,3.21；O,1.87。
实施例9(化合物73)
现提供该化合物的具体合成路线：
Figure BDA0001116294210000171
250ml的四口瓶，氮气保护下，加入0.01mol中间体I，0.011mol二苯胺，0.03mol叔丁醇钠，1×10-4mol Pd2(dba)3，1×10-4mol三叔丁基膦，150ml甲苯，加热回流20小时，反应完全；自然冷却，过滤，滤液旋蒸，过硅胶柱，用甲苯:乙醇＝1:2(体积比)混合溶剂打浆，重结晶后白色固体，纯度(HPLC)为98.2％，收率54.2％。
元素分析结构(分子式C52H37NO)：理论值C,90.27；H,5.39；N,2.02；O,2.31；
测试值：C,90.31；H,5.42；N,2.01；O,2.26。
实施例10(化合物85)
现提供该化合物的具体合成路线：
Figure BDA0001116294210000172
250ml的四口瓶，氮气保护下，加入0.01mol中间体J，0.011mol(3-二苯胺基)咔唑，0.03mol叔丁醇钠，1×10-4mol Pd2(dba)3，1×10-4mol三叔丁基膦，150ml甲苯，加热回流20小时，反应完全；自然冷却，过滤，滤液旋蒸，过硅胶柱，用甲苯:乙醇＝1:2(体积比)混合溶剂打浆，重结晶后白色固体，纯度(HPLC)为98.1％，收率52.5％。
元素分析结构(分子式C61H38N2O2)：理论值C,88.17；H,4.61；N,3.37；O,3.85；
测试值：C,88.21；H,4.62；N,3.39；O,3.78。
实施例11(化合物98)
现提供该化合物的具体合成路线：
Figure BDA0001116294210000181
250ml的四口瓶，氮气保护下，加入0.01mol中间体K，0.025mol二苯胺，0.03mol叔丁醇钠，1×10-4mol Pd2(dba)3，1×10-4mol三叔丁基膦，150ml甲苯，加热回流20小时，反应完全；自然冷却，过滤，滤液旋蒸，过硅胶柱，用甲苯:乙醇＝1:2.5(体积比)混合溶剂打浆，重结晶后白色固体，纯度(HPLC)为98.1％，收率60.8％。
元素分析结构(分子式C56H46N2)：理论值C,90.04；H,6.21；N,3.75
测试值：C,89.89；H,6.15；N,3.87
实施例12(化合物107)
现提供该化合物的具体合成路线：
Figure BDA0001116294210000182
250ml的四口瓶，氮气保护下，加入0.01mol中间体L，0.011mol(3-二苯胺基)咔唑，0.03mol叔丁醇钠，1×10-4mol Pd2(dba)3，1×10-4mol三叔丁基膦，150ml甲苯，加热回流20小时，反应完全；自然冷却，过滤，滤液旋蒸，过硅胶柱，用甲苯:乙醇＝1:2(体积比)混合溶剂打浆，重结晶后白色固体，纯度(HPLC)为98.1％，收率52.5％。
元素分析结构(分子式C66H46N2)：理论值C,91.42；H,5.35；N,3.23；
测试值：C,91.38；H,5.38；N,3.24
本发明化合物可以作为发光层掺杂材料使用。对本发明化合物25、化合物28、材料MQAB分别进行热稳定性能、荧光量子效率、循环伏安稳定性测定，检测；结果如表1所示。
表1
化合物 Tg(℃) Td(℃) 荧光量子效率 循环伏安特性
化合物25 125 435 90％ 优
化合物28 120 426 92％ 优
MQAB 102 394 85％ 差
注：热失重温度Td是在氮气气氛中失重1％的温度，在日本岛津公司的TGA-50H热重分析仪上进行测定，氮气流量为20mL/min；Tg日本岛津公司的DSC-60热差扫描分析仪进行测定，氮气流量10mL/min。荧光量子效率采用日本HAMAMATSU公司的Quantaurus-QY(C13534-11)进行鉴定；循环伏安稳定性是通过循环伏安法观测材料的氧化还原特性来进行鉴定；测试条件：测试样品溶于体积比为2:1的二氯甲烷和乙腈混合溶剂，浓度1mg/mL，电解液是0.1M的四氟硼酸四丁基铵或六氟磷酸四丁基铵的有机溶液。参比电极是Ag/Ag+电极，对电极为钛板，工作电极为ITO电极，循环次数为20次。
由上表数据可知，本发明化合物具有较好的氧化还原稳定性，较高的热稳定性和荧光量子效率；可作为发光层掺杂材料使用，从而提升OLED器件效率和寿命。
以下通过对比例1、2和实施例13～27详细说明本发明合成的材料在OLED器件上的应用效果。所述实施例13～27与对对比例1、2相比，所述器件的制作工艺完全相同，并且所采用了相同的基板材料和电极材料，电极材料的膜厚也保持一致，所不同的是对器件中所使用的部分材料进行了一些调整，对比例1、2使用了本发明所述部分OLED材料。
对比例1
透明玻璃基板1采用透明材料。对ITO阳极层2(膜厚为150nm)进行洗涤，即依次进行碱洗涤、纯水洗涤、干燥后再进行紫外线-臭氧洗涤以清除透明ITO表面的有机残留物。
在进行了上述洗涤之后的ITO阳极层2上，利用真空蒸镀装置，蒸镀HAT-CN，其膜厚为10nm，这层有机材料作为空穴注入层3使用。紧接着蒸镀70nm厚度的TCTA(4,4',4″-三(咔唑-9-基)三苯胺)作为空穴传输层4。
上述空穴传输材料蒸镀结束后，制作OLED发光器件的发光层5，其结构包括OLED发光层5所使用材料mCP作为主体材料，MQAB作为掺杂材料，掺杂比例为4％重量比，发光层膜厚为25nm。
在上述发光层5之后，继续真空蒸镀电子传输层材料为TPBi。该材料的真空蒸镀膜厚为35nm，此层为电子传输层6。
在电子传输层6上，通过真空蒸镀装置，制作膜厚为1nm的氟化锂(LiF)层，此层为电子注入层7。
在电子注入层7上，通过真空蒸镀装置，制作膜厚为80nm的铝(Al)层，此层为阴极反射电极层8使用。各层材料结构如下所示：
Figure BDA0001116294210000201
所制作的OLED发光器件结构如表2所示，测试结果如表3所示。
如上所述完成OLED发光器件制作后，用公知的驱动电路将阳极和阴极连接起来，测量器件的发光效率，发光颜色以及器件寿命(LT95：亮度衰减到初始亮度的95％)。
对比例2
TO阳极层2/空穴注入层3(HAT-CN，厚度10nm)/空穴传输层4(TCTA，厚度70nm)/发光层5(NpPhAn和MQAB按照100:4的重量比混掺，厚度25nm)/电子传输层6(TPBi，厚度35nm)/电子注入层7(LiF，厚度1nm)/阴极反射电极层8(Al，厚度80nm)。
实施例13
ITO阳极层2/空穴注入层3(HAT-CN，厚度10nm)/空穴传输层4(TCTA，厚度70nm)/发光层5(mCP和化合物06按照100:4的重量比混掺，厚度25nm)/电子传输层6(TPBi，厚度35nm)/电子注入层7(LiF，厚度1nm)/阴极反射电极层8(Al，厚度80nm)。
实施例14
ITO阳极层2/空穴注入层3(HAT-CN，厚度10nm)/空穴传输层4(TCTA，厚度70nm)/发光层5(mCP和化合物11按照100:4的重量比混掺，厚度25nm)/电子传输层6(TPBi，厚度35nm)/电子注入层7(LiF，厚度1nm)/阴极反射电极层8(Al，厚度80nm)。
实施例15
ITO阳极层2/空穴注入层3(HAT-CN，厚度10nm)/空穴传输层4(TCTA，厚度70nm)/发光层5(mCP和化合物15按照100:4的重量比混掺，厚度25nm)/电子传输层6(TPBi，厚度35nm)/电子注入层7(LiF，厚度1nm)/阴极反射电极层8(Al，厚度80nm)。
实施例16
ITO阳极层2/空穴注入层3(HAT-CN，厚度10nm)/空穴传输层4(TCTA，厚度70nm)/发光层5(mCP和化合物25按照100:4的重量比混掺，厚度25nm)/电子传输层6(TPBi，厚度35nm)/电子注入层7(LiF，厚度1nm)/阴极反射电极层8(Al，厚度80nm)。
实施例17
ITO阳极层2/空穴注入层3(HAT-CN，厚度10nm)/空穴传输层4(TCTA，厚度70nm)/发光层5(mCP和化合物28按照100:4的重量比混掺，厚度25nm)/电子传输层6(TPBi，厚度35nm)/电子注入层7(LiF，厚度1nm)/阴极反射电极层8(Al，厚度80nm)。
实施例18
ITO阳极层2/空穴注入层3(HAT-CN，厚度10nm)/空穴传输层4(TCTA，厚度70nm)/发光层5(mCP和化合物33按照100:4的重量比混掺，厚度25nm)/电子传输层6(TPBi，厚度35nm)/电子注入层7(LiF，厚度1nm)/阴极反射电极层8(Al，厚度80nm)。
实施例19
ITO阳极层2/空穴注入层3(HAT-CN，厚度10nm)/空穴传输层4(TCTA，厚度70nm)/发光层5(mCP和化合物38按照100:4的重量比混掺，厚度25nm)/电子传输层6(TPBi，厚度35nm)/电子注入层7(LiF，厚度1nm)/阴极反射电极层8(Al，厚度80nm)。
实施例20
ITO阳极层2/空穴注入层3(HAT-CN，厚度10nm)/空穴传输层4(TCTA，厚度70nm)/发光层5(mCP和化合物57按照100:4的重量比混掺，厚度25nm)/电子传输层6(TPBi，厚度35nm)/电子注入层7(LiF，厚度1nm)/阴极反射电极层8(Al，厚度80nm)。
实施例21
ITO阳极层2/空穴注入层3(HAT-CN，厚度10nm)/空穴传输层4(TCTA，厚度70nm)/发光层5(mCP和化合物73按照100:4的重量比混掺，厚度25nm)/电子传输层6(TPBi，厚度35nm)/电子注入层7(LiF，厚度1nm)/阴极反射电极层8(Al，厚度80nm)。
实施例22
ITO阳极层2/空穴注入层3(HAT-CN，厚度10nm)/空穴传输层4(TCTA，厚度70nm)/发光层5(mCP和化合物85按照100:4的重量比混掺，厚度25nm)/电子传输层6(TPBi，厚度35nm)/电子注入层7(LiF，厚度1nm)/阴极反射电极层8(Al，厚度80nm)。
实施例23
ITO阳极层2/空穴注入层3(HAT-CN，厚度10nm)/空穴传输层4(TCTA，厚度70nm)/发光层5(mCP和化合物98按照100:4的重量比混掺，厚度25nm)/电子传输层6(TPBi，厚度35nm)/电子注入层7(LiF，厚度1nm)/阴极反射电极层8(Al，厚度80nm)。
实施例24
ITO阳极层2/空穴注入层3(HAT-CN，厚度10nm)/空穴传输层4(TCTA，厚度70nm)/发光层5(mCP和化合物107按照100:4的重量比混掺，厚度25nm)/电子传输层6(TPBi，厚度35nm)/电子注入层7(LiF，厚度1nm)/阴极反射电极层8(Al，厚度80nm)。
实施例25
ITO阳极层2/空穴注入层3(HAT-CN，厚度10nm)/空穴传输层4(TCTA，厚度70nm)/发光层5(NpPhAn和化合物85按照100:4的重量比混掺，厚度25nm)/电子传输层6(TPBi，厚度35nm)/电子注入层7(LiF，厚度1nm)/阴极反射电极层8(Al，厚度80nm)。
实施例26
ITO阳极层2/空穴注入层3(HAT-CN，厚度10nm)/空穴传输层4(TCTA，厚度70nm)/发光层5(NpPhAn和化合物98按照100:4的重量比混掺，厚度25nm)/电子传输层6(TPBi，厚度35nm)/电子注入层7(LiF，厚度1nm)/阴极反射电极层8(Al，厚度80nm)。
实施例27
ITO阳极层2/空穴注入层3(HAT-CN，厚度10nm)/空穴传输层4(TCTA，厚度70nm)/发光层5(NpPhAn和化合物107按照100:4的重量比混掺，厚度25nm)/电子传输层6(TPBi，厚度35nm)/电子注入层7(LiF，厚度1nm)/阴极反射电极层8(Al，厚度80nm)。
表2
Figure BDA0001116294210000231
Figure BDA0001116294210000241
表3
器件代号 发光效(cd/A) 颜色 LT95寿命(H)
对比例1 3.0 蓝色 2.0
对比例2 3.6 蓝色 2.5
实施例13 4.6 蓝色 3.1
实施例14 4.8 蓝色 3.0
实施例15 5.0 蓝色 3.2
实施例16 4.7 蓝色 3.0
实施例17 4.2 蓝色 3.1
实施例18 3.8 蓝色 2.8
实施例19 4.0 蓝色 3.2
实施例20 4.3 蓝色 3.3
实施例21 4.4 蓝色 2.9
实施例22 4.5 蓝色 3.2
实施例23 4.6 蓝色 3.3
实施例24 3.8 蓝色 2.7
实施例25 5.2 蓝色 3.3
实施例26 4.8 蓝色 3.5
实施例27 5.3 蓝色 3.0
注：以上数据都是以对比例1作为标准器件，对比例1的电流效率为3.0cd/A(@10mA/cm2)；CIE色坐标为(0.15，0.15)；1000亮度下LT95寿命衰减为2Hr。寿命测试系统为本发明所有权人与上海大学共同研究的OLED器件寿命测试仪。
由表3的结果可以看出，本发明所述化合物可应用于OLED发光器件制作，并且可以获得良好的器件表现。器件的发光效率和寿命均得到很大改善。本发明所述化合物在OLED发光器件中具有良好的应用效果，并具有良好的产业化前景。
虽然已通过实施例和优选实施方式公开了本发明，但应理解，本发明不限于所公开的实施方式。相反，本领域技术人员应明白，其意在涵盖各种变型和类似的安排。因此，所附权利要求的范围应与最宽的解释相一致以涵盖所有这样的变型和类似的安排。

Claims (4)

1.一种有机电致发光材料，其特征在于所述发光材料选自通式(1a)-(3a)的任一种：
Figure FDA0002438331240000011
R3、R4分别独立的表示为氢、甲基、苯基；R2表示为通式(4)、(5)、(6)中的一种：
Figure FDA0002438331240000012
a选自
Figure FDA0002438331240000013
中的一种；
a与C5-C6键、C6-C7键、或C7-C8键连接；
X1、X2、X3分别独立的表示为氧原子、硫原子、甲基取代的亚甲基；
X4、X5分别独立的表示为氢、甲基、或苯基；
所述Ra、R5分别独立的采用通式(7)、(8)或通式(9)表示：
Figure FDA0002438331240000021
通式(7)、(8)中，X6为氧原子、硫原子或甲基取代的亚甲基的一种；
R6、R7分别独立的表示为氢、碳原子数1-6的烷基、苯基、吡啶基、二联苯基、三联苯基、萘基、蒽基、菲基、三嗪基、嘧啶基、喹啉基、二苯并呋喃基、二苯并噻吩基、9,9-二甲基芴基、9,9-二苯基芴基；
Figure FDA0002438331240000022
R8、R9分别独立的表示为苯基、9,9-二甲基芴基、二苯并呋喃基或者萘基中的一种。
2.根据权利要求1所述的有机电致发光材料，其特征在于所述发光材料的具体结构为：
Figure FDA0002438331240000023
Figure FDA0002438331240000031
Figure FDA0002438331240000032
的任一种。
3.一种有机电致发光材料，其特征在于所述发光材料的结构式为：
Figure FDA0002438331240000033
Figure FDA0002438331240000041
Figure FDA0002438331240000051
Figure FDA0002438331240000061
Figure FDA0002438331240000071
Figure FDA0002438331240000081
Figure FDA0002438331240000082
中的任一种。
4.一种含有权利要求1-3任一项所述有机电致发光材料的有机电致发光器件，其特征在于所述材料作为发光层掺杂材料应用于有机电致发光二极管。
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Publication number Priority date Publication date Assignee Title
KR20120093076A (ko) * 2011-02-14 2012-08-22 에스에프씨 주식회사 플루오렌 유도체 및 이를 포함하는 유기전계발광소자
CN105254561A (zh) * 2015-11-10 2016-01-20 江苏三月光电科技有限公司 一种用于oled的含芴有机化合物及其应用

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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CN105254561A (zh) * 2015-11-10 2016-01-20 江苏三月光电科技有限公司 一种用于oled的含芴有机化合物及其应用

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