CN107235858A - 一种具有电子传输效应的有机电致发光材料及其有机发光器件 - Google Patents

一种具有电子传输效应的有机电致发光材料及其有机发光器件 Download PDF

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CN107235858A
CN107235858A CN201710568857.7A CN201710568857A CN107235858A CN 107235858 A CN107235858 A CN 107235858A CN 201710568857 A CN201710568857 A CN 201710568857A CN 107235858 A CN107235858 A CN 107235858A
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孙可
孙可一
蔡辉
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Abstract

本发明提供一种具有电子传输效应的有机电致发光材料及其有机发光器件，属于有机光电材料技术领域。解决现有技术中有机光电材料发光效率低、驱动电压较高、使用寿命短等发光性能差的技术问题。与现有技术相比，本发明的基于一种具有电子传输效应的有机电致发光材料及其有机发光器件，驱动电压最低为3.9V，发光效率最高可达21.4cd/A，是一种优异的OLED材料。

Description

一种具有电子传输效应的有机电致发光材料及其有机发光 器件
技术领域
本发明涉及有机光电材料技术领域，具体涉及一种具有电子传输效应的有机电致发光材料及其有机发光器件。
背景技术
有机电致发光器件具有包括发光层和在发光层两侧的一对电极所构成。当在两个电极之间施加电场时，电子由负极注入，空穴由正极注入，在发光层中电子和空穴重新结合形成激发态，当激发态返回到基态时产生的能量发射光。
有机电致发光材料已经发展了相当长的一段时间，荧光材料作为第一代发光材料经常被用在发光层中。除此之外，磷光材料作为第二代发光主体材料也受到相当的重视。如Applied Physics letters,Vol 74,No.3,P442-444,1999；US patent 6097147,6306238等。
在使用磷光材料制备的有机发光器件中，空穴传输材料的迁移率远远大于电子传输材料的迁移率，是电子传输材料迁移率的100倍，约10-3cm2/Vs。拥有较好的电子迁移率，才能够有效地将电子传输到远离阴极的复合区域。另外，电子传输材料要有较好的成膜性，否则在蒸镀或旋涂时，不能形成均匀的薄膜，容易产生结晶，严重影响器件的效率和寿命。当前，最常用的电子传输材料通常含有氮杂环类的缺电子的芳环类化合物以及金属配合物，比如Alq3，BAlq、Gaq3、Inq3、Liq、ZnBPO等。由于材料性能的影响，反映到器件上来，器件的驱动电压或者发光效率都不理想。
为突破磷光材料在发光器件的应用限制，本发明构思了一种具有电子传输效应的有机电致发光材料及其有机发光装置，本发明人基于从事此类产品设计制造多年丰富的实务经验和专业知识，并配合学理的运用，积极加以创新，以期创设一种新型结构的有机发光材料和发光器件。
发明内容
本发明提供了一种具有电子传输效应的有机电致发光材料。采用本发明所述一种具有电子传输效应的有机电致发光材料制备的有机发光器件，具有更低的驱动电压、更高的发光效率。
本发明首先提供了一种具有电子传输效应的有机电致发光材料，具有如式I所示的结构式：
其中，R选自氢、取代或未取代的C6-C60芳基、取代或未取代的C6-C60稠环芳基、取代或未取代的C7-C60芳烷基、取代或未取代的C7-C60芳胺基、取代或未取代的C7-C60芳醚基、取代或未取代的C7-C60芳硫醚基、取代或未取代的C6-C60芳基膦、取代或未取代的C4-C60的芳香族杂环基中的任意一种。
优选的，所述的R选自氢、取代或未取代的C6-C30芳基、取代或未取代的C6-C30稠环芳基、取代或未取代的C7-C30芳烷基、取代或未取代的C7-C30芳胺基、取代或未取代的C7-C30芳醚基、取代或未取代的C7-C30芳硫醚基、取代或未取代的C6-C30芳基膦、取代或未取代的C4-C30的芳香族杂环基中的任意一种。
优选的，所述一种具有电子传输效应的有机电致发光材料，选自如下结构中的任意一种：
本发明还提供一种具有电子传输效应的有机电致发光材料的有机发光器件，包括第一电极、第二电极和置于所述两电极之间的一个或多个有机化合物层，至少一个有机化合物层包含至少一种具有电子传输效应的有机电致发光材料。
优选的，所述有机化合物层包括空穴注入层、空穴传输层、发光层、空穴阻挡层、电子传输层、电子注入层中的至少一层。
本发明的有益效果：
与现有技术相比，本发明的一种具有电子传输效应的有机电致发光材料的有机发光器件，驱动电压最低为3.9V，发光效率最高可达21.4cd/A，是一种优异的OLED材料。
具体实施方式
下面将结合本发明实施例的技术方案进行清楚、完整地描述，显然，所描述的实施例仅仅是本发明一部分实施例，而不是全部的实施例。基于本发明中的实施例，本领域普通技术人员在没有做出创造性劳动前提下所获得的所有其他实施例，都属于本发明保护的范围。
本发明首先提供一种具有电子传输效应的有机电致发光材料，具有如式I所示的结构式：
其中，R选自氢、取代或未取代的C6-C60芳基、取代或未取代的C6-C60稠环芳基、取代或未取代的C7-C60芳烷基、取代或未取代的C7-C60芳胺基、取代或未取代的C7-C60芳醚基、取代或未取代的C7-C60芳硫醚基、取代或未取代的C6-C60芳基膦、取代或未取代的C4-C60的芳香族杂环基中的任意一种。
优选的，所述的R选自氢、取代或未取代的C6-C30芳基、取代或未取代的C6-C30稠环芳基、取代或未取代的C7-C30芳烷基、取代或未取代的C7-C30芳胺基、取代或未取代的C7-C30芳醚基、取代或未取代的C7-C30芳硫醚基、取代或未取代的C6-C30芳基膦、取代或未取代的C4-C30的芳香族杂环基中的任意一种。
按照本发明，所述取代的芳基、取代的芳烷基、取代的芳胺、取代的杂芳基中，所述取代基可选自C1～C4烷基、C6-C18芳基，所述取代基的个数优选为1～3个。所述杂芳基中的杂原子优选为O、S、N或P。
优选的，所述一种具有电子传输效应的有机电致发光材料，选自如下结构中的任意一种：
本发明所述一种具有电子传输效应的有机电致发光材料的有机发光材料的制备方法如下：
其中，R选自氢、取代或未取代的C6-C60芳基、取代或未取代的C6-C60稠环芳基、取代或未取代的C7-C60芳烷基、取代或未取代的C7-C60芳胺基、取代或未取代的C7-C60芳醚基、取代或未取代的C7-C60芳硫醚基、取代或未取代的C6-C60芳基膦、取代或未取代的C4-C60的芳香族杂环基中的任意一种。
本发明对上述各类反应的反应条件没有特殊要求，以本领域技术人员熟知的此类反应的常规条件即可。本发明对上述各类反应中所采用的原料的来源没有特别的限制，可以为市售产品或采用本领域技术人员所熟知的制备方法制备得到。其中，所述R的选择同上所述，在此不再赘述。
本发明还提供一种具有电子传输效应的有机电致发光材料的有机发光器件，所述有机发光器件为本领域技术人员所熟知的有机发光器件即可。本发明所述有机发光器件包括第一电极、第二电极和置于两电极之间的一个或多个有机化合物层，至少一个有机化合物层包含至少一种本发明所述的一种具有电子传输效应的有机电致发光材料的有机发光材料。所述有机化合物层优选包括空穴注入层、空穴传输层、发光层、空穴阻挡层、电子传输层与电子注入层中的至少一层，优选所述的电子传输层中含有本发明所述的一种具有电子传输效应的有机电致发光材料。
实施例1：化合物1的制备
Step1，向刚从鼓风干燥箱拿出的三口瓶中加入溴化卞100mmol，无水氯化镁1.5当量，配体联吡啶0.15当量，活化锌粉3当量。在氮气保护下，加入Ni(COD)2 0.1当量，之后再氮气保护下，加入溶剂乙腈，和酰氯。室温下反应12h。反应完成后，经由柱层析，得到产品41mmol(1-1)。
Step2，将9.2g金属钠溶解在185ml绝对乙醇中，将此溶液降温到0℃，逐渐滴加二苄基甲酮42g，和草酸二乙酯30g。反应液在零摄氏度下反应3h，逐渐升温到室温反应48h。反应完成后，逐渐滴加冰醋酸到反应液中性。反应液过硅藻土漏斗，除掉少量的油状物。滴加100ml 2N浓硫酸，有明黄色固体产生。过滤，滤饼用水洗涤。干燥。粗品用二甲苯重结晶三次，再用乙醇重结晶两次，得到淡黄色针状晶体，37mmol(1-2)。
Step3，将37mmol(1-2)，和80mmol丙二腈溶解在乙二醇中，100℃下反应3h，将反应液倒入水中，有固体沉淀析出，过滤。得到粗品，经由柱层析，得到产品30mmol化合物1。
实施例2：化合物2的合成
Step1，向刚从鼓风干燥箱拿出的三口瓶中加入1-溴-4-(溴甲基)苯100mmol，无水氯化镁1.5当量，配体联吡啶0.15当量，活化锌粉3当量。在氮气保护下，加入Ni(COD)2 0.1当量，之后再氮气保护下，加入溶剂乙腈，和2-(4-溴苯基)乙酰氯。室温下反应12h。反应完成后，经由柱层析，得到产品41mmol(2-1)。
Step2，将9.2g金属钠溶解在185ml绝对乙醇中，将此溶液降温到0℃，逐渐滴加2-142g，和草酸二乙酯30g。反应液在零摄氏度下反应3h，逐渐升温到室温反应48h。反应完成后，逐渐滴加冰醋酸到反应液中性。反应液过硅藻土漏斗，除掉少量的油状物。滴加100ml2N浓硫酸，有明黄色固体产生。过滤，滤饼用水洗涤。干燥。粗品用二甲苯重结晶三次，再用乙醇重结晶两次，得到淡黄色针状晶体，37mmol(2-2)。
Step3，将37mmol(2-2)，和80mmol丙二腈溶解在乙二醇中，100℃下反应.3h，将反应液倒入水中，有固体沉淀析出，过滤。得到粗品，经由柱层析，得到产品30mmol化合物2-3。
Step4，将化合物2-3 30mmol，加入60mmol的苯硼酸，90mmol碳酸钠，0.3mmol Pd(PPh3)4，甲苯，乙醇、水比例为(4:1:1)的混合溶剂，氩气置换三次回流温度下反应10h，粗产品经由柱层析，得到产品22mmol化合物2。
实施例3：化合物6的合成
同实施例2，将step4中的苯硼酸替换为对氰基苯硼酸。
实施例4：化合物8的合成
同实施例2，将step4中的苯硼酸替换为9,9-二甲基芴-2-硼酸。
实施例5：化合物10的合成
Step1，向刚从鼓风干燥箱拿出的三口瓶中加入1-溴-4-(溴甲基)苯100mmol，无水氯化镁1.5当量，配体联吡啶0.15当量，活化锌粉3当量。在氮气保护下，加入Ni(COD)2 0.1当量，之后再氮气保护下，加入溶剂乙腈，和2-(4-溴苯基)乙酰氯。室温下反应12h。反应完成后，经由柱层析，得到产品41mmol(2-1)。
Step2，将9.2g金属钠溶解在185ml绝对乙醇中，将此溶液降温到0℃，逐渐滴加2-142g，和草酸二乙酯30g。反应液在零摄氏度下反应3h，逐渐升温到室温反应48h。反应完成后，逐渐滴加冰醋酸到反应液中性。反应液过硅藻土漏斗，除掉少量的油状物。滴加100ml2N浓硫酸，有明黄色固体产生。过滤，滤饼用水洗涤。干燥。粗品用二甲苯重结晶三次，再用乙醇重结晶两次，得到淡黄色针状晶体，37mmol(2-2)。
Step3，将37mmol(2-2)，和80mmol丙二腈溶解在乙二醇中，100℃下反应3h，将反应液倒入水中，有固体沉淀析出，过滤。得到粗品，经由柱层析，得到产品30mmol化合物2-3。
Step4，将2-3 30mmol，加入60mmol的二苯胺，90mmol叔丁醇钾，0.3mmol Pd2(dba)3，甲苯，氩气置换三次，加入0.6mmol三叔丁基膦，再次氩气置换三次，回流温度下反应10h，过柱，得到产品10 22mmol。
实施例6：化合物21的合成
合成方法同实施例2。将step4中的苯硼酸替换为吡啶-4-硼酸。
实施例7：化合物23的合成
合成方法同实施例2。将step4中的苯硼酸替换为吡啶-3-硼酸。
实施例8：化合物29的合成
合成方法同实施例2。将step4中的苯硼酸替换为二苯并呋喃-2-硼酸。
实施例9：化合物30的合成
合成方法同实施例2。将step4中的苯硼酸替换为二苯并噻吩-2-硼酸。
实施例10：化合物32的合成
合成方法同实施例2。将step4中的苯硼酸替换为4-苯氧基苯基硼酸。
实施例11：化合物33的合成
合成方法同实施例2。将step4中的苯硼酸替换为4-苯硫基苯基硼酸。
本发明实施例制备得到的一种具有电子传输效应的有机电致发光材料的FD-MS值见表1所示。
表1本发明实施例制备的化合物FD-MS值
对比应用实施例1：
取ITO透明玻璃为阳极，超声清洗后干燥至于真空腔中，抽真空至5×10-5Pa，在上述阳极基板上真空蒸镀NPB作为空穴传输层，蒸镀速率为0.1nm/s，蒸镀厚度为70nm。在空穴传输层上真空蒸镀BND/FIrpic作为发光层，掺杂浓度为10wt％，蒸镀速率为0.005nm/s，蒸镀厚度为30nm。在发光层上真空蒸镀Alq3作为电子传输层，蒸镀速率为0.01nm/s，蒸镀厚度为50nm。在电子传输层上真空蒸镀Al层作为阴极，厚度为200nm。
应用实例1：
取ITO透明玻璃为阳极，超声清洗后干燥至于真空腔中，抽真空至5×10-5Pa，在上述阳极基板上真空蒸镀NPB作为空穴传输层，蒸镀速率为0.1nm/s，蒸镀厚度为70nm。在空穴传输层上真空蒸镀BND/FIrpic作为发光层，掺杂浓度为10wt％，蒸镀速率为0.005nm/s，蒸镀厚度为30nm。在发光层上真空蒸镀化合物1作为电子传输层，蒸镀速率为0.01nm/s，蒸镀厚度为50nm。在电子传输层上真空蒸镀Al层作为阴极，厚度为200nm。
应用实例2：
将应用实施例1中的化合物1换成化合物2。测量该器件的发光性能，结果见表2。
应用实例3：
将应用实施例1中的化合物1换成化合物6。测量该器件的发光性能，结果见表2。
应用实例4：
将应用实施例1中的化合物1换成化合物8。测量该器件的发光性能，结果见表2。
应用实例5：
将应用实施例1中的化合物1换成化合物10。测量该器件的发光性能，结果见表2。
应用实例6：
将应用实施例1中的化合物1换成化合物21。测量该器件的发光性能，结果见表2。
应用实例7：
将应用实施例1中的化合物1换成化合物23。测量该器件的发光性能，结果见表2。
应用实例8：
将应用实施例1中的化合物1换成化合物29。测量该器件的发光性能，结果见表2。
应用实例9：
将应用实施例1中的化合物1换成化合物30。测量该器件的发光性能，结果见表2。
应用实例10：
将应用实施例1中的化合物1换成化合物32。测量该器件的发光性能，结果见表2。
应用实例11：
将应用实施例1中的化合物1换成化合物33。测量该器件的发光性能，结果见表2。
测量实施例1：对比样品以及样品的发光性能。
对比样品以及样品是采用Keithley SMU235，PR650评价发光效率和发光寿命，结果列于表2中：
表2本发明实施例制备的发光器件的发光特性
以上可以看出，本发明的一种具有电子传输效应的有机电致发光材料在电致发光器件中进行应用，驱动电压最低为3.9V，发光效率最高可达21.4cd/A，较大的提高了器件的发光效率，是性能良好的有机发光材料。
虽然本发明用示范性实施方案进行了特别的描述，但应该理解在不偏离权利要求所限定的本发明的精神与范围的情况下，本领域普通技术人员可对其进行各种形式和细节上的改变。

Claims (5)

1.一种具有电子传输效应的有机电致发光材料，其结构通式如式I所示：
其中，R选自氢、取代或未取代的C6-C60芳基、取代或未取代的C6-C60稠环芳基、取代或未取代的C7-C60芳烷基、取代或未取代的C7-C60芳胺基、取代或未取代的C7-C60芳醚基、取代或未取代的C7-C60芳硫醚基、取代或未取代的C6-C60芳基膦、取代或未取代的C4-C60的芳香族杂环基中的任意一种。
2.根据权利要求1所述的一种具有电子传输效应的有机电致发光材料，其特征在于，R选自氢、取代或未取代的C6-C30芳基、取代或未取代的C6-C30稠环芳基、取代或未取代的C7-C30芳烷基、取代或未取代的C7-C30芳胺基、取代或未取代的C7-C30芳醚基、取代或未取代的C7-C30芳硫醚基、取代或未取代的C6-C30芳基膦、取代或未取代的C4-C30的芳香族杂环基中的任意一种。
3.根据权利要求1所述的一种具有电子传输效应的有机电致发光材料，其特征在于，选自如下结构中的任意一种：
4.一种具有电子传输效应的有机电致发光材料的有机发光器件，包括第一电极、第二电极和置于所述两电极之间的一个或多个有机化合物层，其特征在于，至少一个有机化合物层包含至少一种如权利要求1～3任意一项中所述的一种具有电子传输效应的有机电致发光材料。
5.根据权利要求4所述的一种具有电子传输效应的有机电致发光材料的有机发光器件，其特征在于，所述有机化合物层包括空穴注入层、空穴传输层、发光层、空穴阻挡层、电子传输层、电子注入层中的至少一层。
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