CN107056809B - 一种含有二甲基蒽的有机化合物及其在有机电致发光器件上应用 - Google Patents

一种含有二甲基蒽的有机化合物及其在有机电致发光器件上应用 Download PDF

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CN107056809B
CN107056809B CN201610259280.7A CN201610259280A CN107056809B CN 107056809 B CN107056809 B CN 107056809B CN 201610259280 A CN201610259280 A CN 201610259280A CN 107056809 B CN107056809 B CN 107056809B
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张兆超
王立春
李崇
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Jiangsu Sunera Technology Co Ltd
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Abstract

本发明公开了一种含有二甲基蒽的有机化合物及其在有机电致发光器件上的应用，该有机化合物的结构式通式如通式(1)所示。本发明化合物具有较高的玻璃化温度和分子热稳定性，合适的HOMO和LUMO能级，较高Eg，通过器件结构优化，可有效提升OLED器件的光电性能以及OLED器件的寿命。

Description

一种含有二甲基蒽的有机化合物及其在有机电致发光器件上 应用
技术领域
本发明涉及有机光电材料技术领域，尤其是涉及一种含有二甲基蒽结构为中心骨架的化合物材料及其在OLED领域的应用。
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。
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的正负电荷，正负电荷进一步在发光层中复合，即产生OLED电致发光。
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。
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、电子阻挡材料、空穴注入传输材料和空穴阻挡材料，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，作为发光层的主体材料要求材料具有良好双极性，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、电子阻挡层、发光层、空穴阻挡层、电子传输层、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，电子传输材料等，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。
因此，针对当前OLED器件的产业应用要求，以及OLED器件的不同功能膜层，器件的光电特性需求，必须选择更适合，具有高性能的OLED功能材料或材料组合，才能实现器件的高效率、长寿命和低电压的综合特性。就当前OLED显示照明产业的实际需求而言，目前OLED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含有二甲基蒽的有机化合物及其在有机电致发光器件上应用。本发明化合物含有二甲基蒽结构，具有较高的玻璃化温度和分子热稳定性，合适的HOMO和LUMO能级，较高Eg，通过器件结构优化，可有效提升OLED器件的光电性能以及OLED器件的寿命。
本发明的技术方案如下：
一种含有二甲基蒽的有机化合物，该化合物的结构式通式如通式(1)所示：
其中，R1、R2采用通式(2)表示：
通式(2)中，Ar表示为苯基、联苯基或萘基；X1为氧原子、硫原子、硒原子、C1-10直链或支链烷基取代的亚烷基、芳基取代的亚烷基、烷基或芳基取代的芳基胺中的一种；
R3、R4分别独立的选取氢、通式(3)或通式(4)中结构；
通式(3)中，a选自X2、X3分别独立的表示为氧原子、硫原子、硒原子、C1-10直链或支链烷基取代的亚烷基、芳基取代的亚烷基、烷基或芳基取代的芳基胺中的一种；
通式(3)、通式(4)通过CL1-CL2键、CL2-CL3键、CL3-CL4键、CL4-CL5键、CL‘1-CL’2键、CL‘2-CL’3键、CL‘3-CL’4键或CL‘4-CL’5连接在通式(2)上；
R1与R2可以相同或不同；R1还可以表示为苯基、联苯基或萘基。
所述化合物中当a表示且与CL4-CL5键或CL‘4-CL’5键连接时，X1和X2的位置重叠，只取X1或者X2；X3表示为氧原子、硫原子、硒原子、C1-10直链或支链烷基取代的亚烷基、芳基取代的亚烷基、烷基或芳基取代的芳基胺中的一种。
所述通式(2)中
表示为：
中的任意一种。
所述的有机化合物的具体结构式为：
(54)中的任一种。
一种所述有机化合物的制备方法，该方法的合成路线为：
R1表示为苯基、联苯基或萘基；Ar表示为苯基、联苯基或萘基；
所述制备方法以Ar-Br为原料，通过格氏反应，制得格氏试剂，然后和二甲基蒽酮反应，生成叔醇，叔醇和R1-H通过付-克反应，制得一溴代化合物，然后和通过C-N偶联制得所述化合物。
一种所述有机化合物的制备方法，该方法的合成路线为：
其中：R1表示为通式(2)所示的结构；Ar表示为苯基、联苯基或萘基；
所述制备方法以Ar-Br为原料，通过格氏反应，制得格氏试剂，然后和二甲基蒽酮反应，生成叔醇，叔醇和H-Ar-Br通过付-克反应，制得或二溴代化合物，然后和通过C-N偶联制得所述化合物。
一种包含所述有机化合物的有机电致发光器件，所述有机化合物作为发光层材料应用于阴极和阳极之间，用于制备有机电致发光二极管。
本发明有益的技术效果在于：
本发明化合物是一种有机发光功能层材料，该类材料具有分子间不易结晶、不易聚集、具有良好成膜性的特点，本发明化合物分子中的刚性基团可以提高材料的热稳定性。
本发明化合物结构使得电子和空穴在发光层的分布更加平衡，作为OLED发光器件的发光功能层材料使用时，器件的电流效率，功率效率和外量子效率均得到很大改善，同时HOMO和LUMO能级电子云有效分离的可实现较小的S1-T1态能隙，芳基取代的二甲基蒽搭配本发明范围内的支链可有效提高激子利用率和高荧光辐射效率，尤其是作为发光层材料使用时，可降低高电流密度下的效率滚降，降低器件电压，提高器件的电流效率和寿命。
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。
附图说明
图1为本发明所列举的材料应用于OLED器件的结构示意图；
其中，1为透明基板层，2为ITO阳极层，3为空穴注入层，4为空穴传输/电子阻挡层，5为发光层，6为电子传输/空穴阻挡层，7为电子注入层，8为阴极反射电极层。
具体实施方式
下面结合附图和实施例，对本发明进行具体描述。
实施例1化合物1的合成：
合成路线：
250ml的四口瓶，在通入氮气的气氛下，加入11.8g 1,4-二溴苯(0.05mol)和1.33gMg粉(0.055mol)，60ml四氢呋喃，加热回流4小时，反应完全，生成格式试剂；
11.1g10,10-二甲基蒽酮(0.05mol)溶于50ml四氢呋喃中，滴加上述格式试剂，60℃反应24小时，生成大量白色沉淀，最后加入饱和NHCl4将格式盐转化为醇；反应完毕后，乙醚萃取，干燥旋蒸，石油醚：二氯甲烷混合溶剂(3:2)硅胶柱纯化，得到略带黄色的固体叔醇(收率为88％)；使用DEI-MS来识别该化合物，分子式C22H19BrO，检测值[M+1]+＝379.03，计算值378.06；
按1:2当量取15.2g上述叔醇(0.04mol)和6.2g苯(0.08mol)溶于100ml二氯甲烷中，在室温条件下滴加8ml三氟化硼·乙醚络合物，反应30分钟，加入20ml乙醇和20ml水淬灭反应，用二氯甲烷(20ml*3)萃取，干燥旋蒸，石油醚硅胶柱纯化，用乙醇：二氯甲烷重结晶(收率为81％)；使用DEI-MS来识别该化合物，分子式C28H23Br，检测值[M+1]+＝439.07，计算值438.10；
在250ml的三口瓶中，通氮气保护下，加入4.39g(0.01mol)化合物A，4.08g(0.015mol)化合物B，1.44g(0.015mol)叔丁醇钠，0.15g pd2(dba)3，0.10g三叔丁基磷，100ml甲苯，加热回流24小时，取样点板，反应完全；自然冷却，过滤，滤液旋蒸，柱层析得到目标产物，HPLC纯度98.9％，收率65.57％；
使用DEI-MS来识别该化合物，分子式C46H34N2O，检测值[M+1]+＝631.12，计算值630.27。
实施例2化合物3的合成：
合成路线：
按实施例1中化合物1的合成方法制备，不同点在于用化合物C代替化合物B；
使用DEI-MS来识别该化合物，分子式C49H40N2，检测值[M+1]+＝657.13，计算值656.32。
实施例3化合物15的合成：
合成路线：
按实施例1中化合物1的合成方法制备，不同点在于用化合物D代替化合物B；
使用DEI-MS来识别该化合物，分子式C49H39NO，检测值[M+1]+＝658.15，计算值657.30。
实施例4化合物22的合成：
合成路线：
按实施例1中化合物1的合成方法制备，不同点在于用化合物E代替化合物B；
使用DEI-MS来识别该化合物，分子式C52H38N2O，检测值[M+1]+＝707.13，计算值706.30。
实施例5化合物26的合成：
合成路线：
按实施例1中化合物1的合成方法制备，不同点在于用化合物F代替化合物B；
使用DEI-MS来识别该化合物，分子式C46H33O2，检测值[M+1]+＝632.08，计算值631.25。
实施例6化合物28的合成：
合成路线：
按实施例1中化合物1的合成方法制备，不同点在于第三步反应中用溴苯代替苯生成化合物M，第四步反应中用化合物G代替化合物B；
使用DEI-MS来识别该化合物，分子式C52H38N2O2，检测值[M+1]+＝723.28，计算值722.29。
实施例7化合物32的合成：
合成路线：
按实施例1中化合物1的合成方法制备，不同点在于用化合物H代替化合物B；
使用DEI-MS来识别该化合物，分子式C52H45NO，检测值[M+1]+＝700.48，计算值699.35。
实施例8化合物37的合成：
合成路线：
按实施例1中化合物1的合成方法制备，不同点在于用化合物I代替化合物B；
使用DEI-MS来识别该化合物，分子式C61H46N2O，检测值[M+1]+＝823.55，计算值822.36。
实施例9化合物43的合成：
合成路线：
按实施例1中化合物1的合成方法制备，不同点在于用化合物I代替化合物B；
使用DEI-MS来识别该化合物，分子式C55H41NO2，检测值[M+1]+＝748.33，计算值747.31。
实施例9化合物45的合成：
合成路线：
按实施例1中化合物1的合成方法制备，不同点在于第三步反应中用溴苯代替苯，第四步反应中用化合物K代替化合物B；
使用DEI-MS来识别该化合物，分子式C58H50N2，检测值[M+1]+＝775.62，计算值774.40。
本发明化合物可以作为发光层材料使用，对本发明化合物1、化合物15、化合物45、现有材料CBP分别进行热性能、发光光谱、HOMO能级的测试，检测结果如表1所示。
表1
化合物 Tg(℃) Td(℃) λ<sub>PL</sub>(nm) HOMO能级(ev)
化合物1 132 456 375 -5.88
化合物15 135 391 372 -6.03
化合物45 143 422 381 -5.95
材料CBP 113 353 369 -5.9
注：玻璃化温度Tg由示差扫描量热法(DSC，德国耐驰公司DSC204F1示差扫描量热仪)测定，升温速率10℃/min；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；λPL是样品溶液荧光发射波长，利用日本拓普康SR-3分光辐射度计测定；最高占据分子轨道HOMO能级及最低占据分子轨道LUMO能级是由光电子发射谱仪(AC-2型PESA)测试，测试为大气环境。
由上表数据可知，本发明化合物具有合适的HOMO能级以及合适的发光光谱，本发明二甲基蒽化合物具有较高的热稳定性，使得所制作的含有本发明化合物的OLED器件寿命提升。
本发明化合物作为发光层材料应用于OLED发光器件中。以下通过器件实施例1～11和比较例1～2详细说明本发明合成的OLED材料在器件中作为发光层材料的应用效果。本发明所述器件实施例2～11、比较例1～2与器件实施例1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，所不同的是器件2～10对器件中的发光层5的主体材料做了变换；器件11使用本发明所述材料作为空穴传输/电子阻挡层应用。各实施例所得器件的性能测试结果如表2所示。
器件实施例1
一种电致发光器件，其制备步骤包括：
a)清洗透明基板层1上的ITO阳极层2，分别用去离子水、丙酮、乙醇超声清洗各15分钟，然后在等离子体清洗器中处理2分钟；
b)在ITO阳极层2上，通过真空蒸镀方式蒸镀空穴传输层材料HAT-CN，厚度为10nm，这层作为空穴注入层3；
c)在空穴注入层3上，通过真空蒸镀方式蒸镀空穴传输材料NPB，厚度为80nm，该层为空穴传输层/电子阻挡层4；
d)在空穴传输/电子阻挡层4之上蒸镀发光层5，使用本发明化合物1作为作为主体材料，Ir(ppy)3作为掺杂材料，材料掺杂质量比为10％，厚度为30nm；
e)在发光层5之上，通过真空蒸镀方式蒸镀电子传输材料TPBI，厚度为40nm，这层有机材料作为空穴阻挡/电子传输层6使用；
f)在空穴阻挡/电子传输层6之上，真空蒸镀电子注入层LiF，厚度为1nm，该层为电子注入层7；
g)在电子注入层7之上，真空蒸镀阴极Mg：Ag/Ag层，Mg:Ag掺杂比例为9:1，厚度15nm，Ag厚度3nm，该层为阴极反射电极层8；
按照上述步骤完成电致发光器件的制作后，测量器件的电流效率和寿命，其结果见表2所示。
器件实施例2
本实施例与器件实施例1的不同之处在于：电致发光器件的发光层主体材料变为本发明化合物3，掺杂材料为Ir(ppy)3，掺杂质量比为10％，所得电致发光器件的检测数据见表2所示。
器件实施例3
本实施例与器件实施例1的不同之处在于：电致发光器件的发光层主体材料变为本发明化合物15和化合物GHN，掺杂材料为Ir(ppy)3，三种材料的混掺质量比为60:30:10，所得电致发光器件的检测数据见表2所示。
器件实施例4
本实施例与器件实施例1的不同之处在于：电致发光器件的发光层主体材料变为本发明化合物22和化合物GHN，掺杂材料为Ir(ppy)3，三种材料的混掺质量比为60:30:10，所得电致发光器件的检测数据见表2所示。
器件实施例5
本实施例与器件实施例1的不同之处在于：电致发光器件的发光层主体材料变为本发明化合物26和化合物GHN，掺杂材料为Ir(ppy)3，三种材料的混掺质量比为60:30:10，所得电致发光器件的检测数据见表2所示。
器件实施例6
本实施例与器件实施例1的不同之处在于：电致发光器件的发光层主体材料变为本发明化合物28和化合物GHN，掺杂材料为Ir(ppy)3，三种材料的混掺质量比为60:30:10，所得电致发光器件的检测数据见表2所示。
器件实施例7
本实施例与器件实施例1的不同之处在于：电致发光器件的发光层主体材料变为本发明化合物32和化合物GHN，掺杂材料为Ir(ppy)3，三种材料的混掺质量比为60:30:10，所得电致发光器件的检测数据见表2所示。
器件实施例8
本实施例与器件实施例1的不同之处在于：电致发光器件的发光层主体材料变为本发明化合物37和化合物GHN，掺杂材料Ir(ppy)3，三种材料的混掺质量比为60:30:10，所得电致发光器件的检测数据见表2所示。
器件实施例9
本实施例与器件实施例1的不同之处在于：电致发光器件的发光层主体材料变为本发明化合物43和化合物GHN，掺杂材料为Ir(ppy)3，三种材料的混掺质量比为60:30:10，所得电致发光器件的检测数据见表2所示。
器件实施例10
本本实施例与器件实施例1的不同之处在于：电致发光器件的发光层主体材料变为本发明化合物45和化合物GHN，掺杂材料为Ir(ppy)3，三种材料的混掺质量比为60:30:10，所得电致发光器件的检测数据见表2所示。
器件实施例11
本本实施例与器件实施例1的不同之处在于：电致发光器件的空穴传输/电子阻挡层4的材料变为本发明化合物49，发光层5的主体材料为公知化合物CBP，掺杂材料为Ir(ppy)3，掺杂质量比为10％，所得电致发光器件的检测数据见表2所示。
器件比较例1
本实施例与器件实施例1的不同之处在于：电致发光器件的发光层主体材料变为公知化合物CBP，所得电致发光器件的检测数据见表2所示。
表2
注：器件测试性能以器件比较例1作为参照，比较例1器件各项性能指标设为1.0。比较例1的电流效率为28cd/A(@10mA/cm2)；CIE色坐标为(0.33,0.63)；5000亮度下LT95寿命衰减为2.5Hr。
由表2的结果可以看出本发明所述含有二甲基蒽结构的机化合物可应用于OLED发光器件制作，并且与比较例相比，无论是效率还是寿命均比已知OLED材料获得较大改观，特别是器件的寿命衰减获得较大的提升。
综上，以上所述仅为本发明的较佳实施例，并不用以限制本发明，凡在本发明的精神和原则之内，所作的任何修改、等同替换、改进等，均应包含在本发明的保护范围之内。

Claims (7)

1.一种含有二甲基蒽的有机化合物，其特征在于该化合物的结构式通式如通式(1)所示：
其中，R1、R2采用通式(2)表示：
通式(2)中，Ar表示为苯基、联苯基或萘基；X1为氧原子、硫原子、硒原子、甲基取代的亚甲基、苯基取代的亚甲基、苯基取代的叔胺基中的一种；
R3、R4分别独立的选取氢、通式(3)或通式(4)中结构；
通式(3)中，a选自X2、X3分别独立的表示为氧原子、硫原子、硒原子、甲基取代的亚甲基、苯基取代的亚甲基、苯基取代的叔胺基中的一种；
通式(3)、通式(4)通过CL1-CL2键、CL2-CL3键、CL3-CL4键、CL4-CL5键、CL‘1-CL’2键、CL‘2-CL’3键、CL‘3-CL’4键或CL‘4-CL’5连接在通式(2)上；
R1与R2可以相同或不同；R1还可以表示为苯基、联苯基或萘基。
2.根据权利要求1所述的有机化合物，其特征在于所述化合物中当a表示且与CL4-CL5键或CL‘4-CL’5键连接时，X1和X2的位置重叠，只取X1或者X2；X3表示为氧原子、硫原子、硒原子、甲基取代的亚甲基、苯基取代的亚甲基、苯基取代的叔胺基中的一种。
3.根据权利要求1所述的有机化合物，其特征在于所述通式(2)中表示为：
中的任意一种。
4.根据权利要求1所述的有机化合物，其特征在于所述含有二甲基蒽的有机化合物的具体结构式为：
5.一种权利要求1所述有机化合物的制备方法，其特征在于该方法的合成路线为：
R1表示为苯基、联苯基或萘基；Ar表示为苯基、联苯基或萘基；
所述制备方法以Ar-Br为原料，通过格氏反应，制得格氏试剂，然后和二甲基蒽酮反应，生成叔醇，叔醇和R1-H通过付-克反应，制得一溴
代化合物，然后和通过C-N偶联制得所述化合物。
6.一种权利要求1所述有机化合物的制备方法，其特征在于该方法的合成路线为：
其中：R1表示为通式(2)所示的结构；Ar表示为苯基、联苯基或萘基；
所述制备方法以Ar-Br为原料，通过格氏反应，制得格氏试剂，然后和二甲基蒽酮反应，生成叔醇，叔醇和H-Ar-Br通过付-克反应，制得或二溴代化合物，然后和通过C-N偶联制得所述化合物。
7.一种包含权利要求1～5任一项所述有机化合物的有机电致发光器件，其特征在于所述有机化合物作为发光层材料应用于阴极和阳极之间，用于制备有机电致发光二极管。
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