CN110003019A - 一种以均苯为核心的高迁移率有机化合物及其应用 - Google Patents

一种以均苯为核心的高迁移率有机化合物及其应用 Download PDF

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CN110003019A
CN110003019A CN201910279263.3A CN201910279263A CN110003019A CN 110003019 A CN110003019 A CN 110003019A CN 201910279263 A CN201910279263 A CN 201910279263A CN 110003019 A CN110003019 A CN 110003019A
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梁丽
王芳
谢丹丹
吴秀芹
张兆超
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Jiangsu Sanyue Optoelectronic Technology Co Ltd
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Abstract

本发明涉及一种以均苯为核心的具有高迁移率的有机化合物及其应用，本发明提供的有机化合物以均苯为核心，连接芘支链，本发明有机化合物具有良好的热稳定性和较高的玻璃化温度，同时具有合适的HOMO能级，采用本发明提供的有机化合物的器件通过结构优化，可有效提升OLED器件的光电性能以及OLED器件的寿命。

Description

一种以均苯为核心的高迁移率有机化合物及其应用
技术领域
本发明涉及半导体技术领域，尤其涉及一种以均苯为核心的具有高迁移率的有机化合物及其应用。
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。OLED发光器件作为电流器件，当对其两端电极施加电压，并通过电场作用有机层功能材料膜层中的正负电荷时，正负电荷进一步在电子阻挡层中复合，即产生OLED电致发光。
目前对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，创制出更高性能的OLED功能材料。
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性能，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，作为电子阻挡层的主体材料具有良好双极性，适当的HOMO/LUMO能阶等。
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、性能更高的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。就当前的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
本发明的目的之一，是提供一种以均苯为核心的具有高迁移率的有机化合物，其具有良好的热稳定性和较高的玻璃化温度，同时具有合适的HOMO能级，采用本发明提供的有机化合物的器件通过结构优化，可有效提升OLED器件的光电性能以及OLED器件的寿命。
本发明解决上述技术问题的的技术方案如下：一种以均苯为核心的具有高迁移率的有机化合物，所述有机化合物的结构如通式(1)所示：
通式(1)中，Ar1-Ar5分别表示为取代的或未取代的C6-C30芳基、取代的或未取代的C2-C30杂芳基；
所述“取代的”是指至少一个氢原子由以下取代基来替代：金刚烷基、氰基、氟原子、甲基、乙基、丙基、异丙基、叔丁基、戊基、苯基、萘基、联苯基、吡啶基、二苯并呋喃基、咔唑基或呋喃基；
所述杂芳基中的杂原子任选自氮、氧或硫中的一种或多种。
作为本发明的进一步改进，所述Ar1、Ar2、Ar3、Ar4、Ar5分别表示为通式(2)、通式(3)、通式(4)或通式(5)所示结构：
通式(2)中，X1和X2分别独立的表示为单键、O、S、-C(R1R2)-或-NR3-，且X1和X2不同时表示为单键；
R1、R2、R3分别独立地表示为C1-C10的烷基、C3-C10的环烷基、C6-C30芳基、C2-C30杂芳基；
通式(2)、通式(3)、通式(4)、通式(5)和通式(6)中，Y表示为氮原子、碳原子或C-R4，Y每次出现相同或者不同，与其它基团键合时，Y表示为C；R4表示为氢原子、卤素原子、氰基、C1-C20的烷基、C3-C20的环烷基、C1-C20的烷氧基、C6-C30芳基、C2-C30杂芳基。
作为本发明的进一步改进，所述Ar1、Ar2、Ar3、Ar4、Ar5至少有一个表示为通式(2)或通式(3)所示结构。
作为本发明的进一步改进，R1、R2、R3分别独立地表示为甲基、异丙基、叔丁基、金刚烷基、苯基、联苯基、萘基、二甲基芴基、二苯并呋喃基、咔唑基、二苯并噻吩基、吡啶基、萘啶基或咔唑啉基；所述R4表示为为氢原子、氟原子、氰基、甲氧基、甲基、异丙基、叔丁基、金刚烷基、苯基、联苯基、萘基、二甲基芴基、二苯基芴基、螺芴基、二苯并呋喃基、咔唑基、二苯并噻吩基、吡啶基、萘啶基或咔唑啉基。
作为本发明的进一步改进，所述有机化合物的具体结构表示为以下结构中的任一种：
中的任一种。
本发明的目的之二，是提供上述有机化合物的制备方法。本发明的制备方法简单，市场前景广阔，适合规模化生产。
本发明解决上述技术问题的技术方案如下：一种均苯为核心的有机化合物的制备方法，所述制备方法涉及的反应方程式为：
具体制备方法如下：250mL的三口瓶，在通入氮气的气氛下，加入中间体C、原料D、叔丁醇钾、Pd2(dba)3、三苯基膦及150mL溶剂甲苯，加热回流12小时，取样点板，反应完全；自然冷却，过滤，滤液旋蒸，过硅胶柱，得到目标产物；
其中，所述原料D和中间体C的摩尔比为(1.0-3.0):1，叔丁醇钾与中间体C的摩尔比为(1-5):1，Pd2(dba)3与中间体C的摩尔比为(0.01-0.03):1，三苯基膦与中间体C摩尔比为(0.01-0.03):1；甲苯的用量为每1mol中间体C用(100-150)mL甲苯。
本发明的第三个方面是提供一种有机电致发光器件，包括阴极和阳极，所述阴极和阳极之间设置有有机功能层，具有这样的特征，上述有机功能层含有上述有机化合物。
作为本发明的进一步改进，所述有机功能层包括空穴传输层或电子阻挡层，具有这样的特征，上述空穴传输层或电子阻挡层含有上述有机化合物。
本发明的第五个方面是提供一种照明或显示元件，具有这样的特征，包括上述的有机电致发光器件。
本发明有益的技术效果在于：
1.本发明的有机化合物的结构使得电子和空穴在电子阻挡层的分布更加平衡，在恰当的HOMO能级下，提升了空穴注入和传输性能；在合适的LUMO能级下，又起到了电子阻挡的作用，提升激子在电子阻挡层中的复合效率；作为OLED发光器件的电子阻挡层材料使用时，可有效提高激子利用率和荧光辐射效率，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。
2.本发明的有机化合物在OLED器件应用时，通过器件结构优化，可保持高的膜层稳定性，可有效提升OLED器件的光电性能以及OLED器件的寿命。本发明所述化合物在OLED发光器件中具有良好的应用效果和产业化前景。
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、透明基板层，2、ITO阳极层，3、空穴注入层，4、空穴传输层5、电子阻挡层，6、电子阻挡层，7、空穴阻挡/电子传输层，8、电子注入层，9、阴极层，10、CPL层。
图2为本发明制备的器件和对比器件在不同温度下测量的效率曲线图。
具体实施方式
下面将结合本发明实施例中的附图，对本发明实施例中的技术方案进行清楚、完整地描述。
下述制备实施例中所有原料均采购于烟台万润精细化工股份有限公司。
具体制备方法如下：250ml的三口瓶，在通入氮气的气氛下，加入0.01mol原料A1，0.014mol的原料B1，0.03mol叔丁醇钾，1.4×10-4mol Pd2(dba)3，1.3×10-4mol三苯基膦，150ml甲苯，加热至100℃回流12小时，取样点板，反应完全；自然冷却，过滤，滤液旋蒸，过硅胶柱，得到中间体C1；HPLC纯度98.6％，收率86.5％；元素分析结构(分子式C36H29N3)：理论值C,85.85；H,5.80；N,8.34；测试值：C,85.87；H,5.81；N,8.34。ESI-MS(m/z)(M+)：理论值为503.24，实测值为503.25。
以中间体C1的合成方法制备中间体C，其中涉及到原料A和原料B具体结构如表1所示。
表1
制备实施例1：化合物1的合成：
具体制备方法如下：250ml的三口瓶，在通入氮气的气氛下，加入0.01mol的中间体C1，加入0.014mol原料D1，0.03mol叔丁醇钾，1.4×10-4mol Pd2(dba)3，1.3×10-4mol三苯基膦，150ml甲苯，加热至110℃回流12小时，取样点板，反应完全；自然冷却，过滤，滤液旋蒸，过硅胶柱，得到化合物1；HPLC纯度99.2％，收率89.1％；元素分析结构(分子式C52H37N3)：理论值C,88.73；H,5.30；N,5.97；测试值：C,88.74；H,5.30；N,5.97。
ESI-MS(m/z)(M+)：理论值为703.30，实测值为703.32。
其余目标化合物的涉及到的反应类型和化合物1的制备步骤涉及到的反应类型相同。
制备实施例2:化合物3的合成
制备实施例3:化合物6的合成
制备实施例4:化合物7的合成
制备实施例5:化合物10的合成
制备实施例6:化合物12的合成
制备实施例7:化合物15的合成
制备实施例8:化合物22的合成
制备实施例9:化合物31的合成
制备实施例10:化合物37的合成
制备实施例11:化合物51的合成
制备实施例12:化合物58的合成
制备实施例13:化合物74的合成
制备实施例14:化合物87的合成
制备实施例15:化合物102的合成
目标化合物制备过程中涉及到的反应物和催化剂的量，以及得到的目标化合物的结构表征如表2所示。
表2
本发明有机化合物在发光器件中使用，具有高的玻璃化转变温度(Tg)和三线态能级(T1)，合适的HOMO、LUMO能级，可以作为空穴传输层和电子阻挡层材料使用。对本发明化合物分别进行热性能、T1能级、HOMO能级、空穴迁移率及Eg测试，结果如表3所示。
表3
注：三线态能级T1是由日立的F4600荧光光谱仪测试，材料的测试条件为2*10- 5mol/L的甲苯溶液；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；最高占据分子轨道HOMO能级是由电离能测试***(IPS-3)以及紫外分光光度计(UV)测试计算所得，测试为大气环境，空穴迁移率测试，将本发明材料制成单电荷器件，用SCLC方法测定；Eg能级：基于材料单膜的紫外分光光度(UV吸收)基线与第一吸收峰的上升侧画切线，用切线和基线交叉点数值算出；同时，可以使用Gaussian16、6-31G(d)基组，B3lyp泛函、TD-FDT算法优化几何结构，进行HOMO、LUMO能级计算，Eg＝|HOMO-LUMO|。
由上表数据可知，本发明化合物具有适当的HOMO能级、Eg以及较高的空穴迁移率，适合作为空穴传输层和电子阻挡层材料；同时，本发明化合物具有较高的热稳定性，使得应用本发明化合物的OLED器件寿命得到提升。
以下通过器件实施例1～37和比较例1详细说明本发明合成的化合物在器件中作为空穴传输层和电子阻挡层的应用效果。器件实施例2～37、器件比较例1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，所不同的是器件实施例2～17中空穴传输层的材料发生了改变；器件实施例18～37中对器件的电子阻挡层材料做了变换，各实施例所得器件的结构如表4所示。
器件实施例1
如图1所示，一种电致发光器件的制备方法，包括如下步骤：
透明基板层1为透明PI膜，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，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，蒸镀膜厚为10nm的HAT-CN作为空穴注入层3使用。接着蒸镀60nm厚度的化合物1作为空穴传输层。随后蒸镀20nm厚度的EB-1作为电子阻挡层。然后制作OLED发光器件的发光层6，其结构包括OLED发光层6所使用GH-1、GH-2作为主体材料，GD-1作为掺杂材料，掺杂材料掺杂比例为10％重量比，发光层膜厚为40nm。在上述发光层6之后，继续真空蒸镀电子传输层材料为ET-1和Liq。该材料的真空蒸镀膜厚为30nm，此层为空穴阻挡/电子传输层7。在空穴阻挡/电子传输层7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8。在电子注入层8上，通过真空蒸镀装置，制作膜厚为15nm的Mg：Ag电极层，此层为阴极层9使用。在阴极层9上，真空蒸镀70nm的CP-1，作为CPL层10。
相关现有材料的结构如下所示：
如上所述地完成OLED发光器件后，用公知的驱动电路将阳极和阴极连接起来，测量器件的电流效率、发光光谱以及器件的寿命。所得器件的测试结果见表5示。
表4
表5
说明:器件测试性能以比较例1作为参照；电流效率均在10mA/cm2条件下测得；寿命测试***为日本System Engineer's Co.,LTD开发的型号为EAS-62C的OLED器件寿命测试仪。
表5的结果表明本发明化合物作为空穴传输层和电子阻挡层材料可应用于OLED发光器件制作，并且与比较例1相比，无论是效率还是寿命均比已知OLED材料获得较大改观，特别是器件的驱动寿命获得较大的提升。
进一步的本发明材料制备的OLED器件在低温下工作时效率也比较稳定，将器件实施例1、8、18和器件比较例1在-10～80℃区间进行效率测试，所得结果如表6和图2所示。
表6
从表6的数据可知，实施例1、8、18为本发明材料和已知材料搭配的器件结构，和器件比较例1相比，不仅低温效率高，而且在温度升高过程中，效率平稳升高。
从以上数据应用来看，本发明化合物作为空穴传输层或电子阻挡层材料在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。

Claims (7)

1.一种以均苯为核心的具有高迁移率的有机化合物，其特征在于，所述有机化合物的结构如通式(1)所示：
通式(1)中，Ar1-Ar5分别表示为取代的或未取代的C6-C30芳基、取代的或未取代的C2-C30杂芳基；
所述“取代的”是指至少一个氢原子由以下取代基来替代：金刚烷基、氰基、氟原子、甲基、乙基、丙基、异丙基、叔丁基、戊基、苯基、萘基、联苯基、吡啶基、二苯并呋喃基、咔唑基或呋喃基；
所述杂芳基中的杂原子任选自氮、氧或硫中的一种或多种。
2.根据权利要求1所述的有机化合物，其特征在于，所述Ar1、Ar2、Ar3、Ar4、Ar5分别表示为通式(2)、通式(3)、通式(4)或通式(5)所示结构：
通式(2)中，X1和X2分别独立的表示为单键、O、S、-C(R1R2)-或-NR3-，且X1和X2不同时表示为单键；
R1、R2、R3分别独立地表示为C1-C10的烷基、C3-C10的环烷基、C6-C30芳基、C2-C30杂芳基；
通式(2)、通式(3)、通式(4)、通式(5)和通式(6)中，Y表示为氮原子、碳原子或C-R4，Y每次出现相同或者不同，与其它基团键合时，Y表示为C；R4表示为氢原子、卤素原子、氰基、C1-C20的烷基、C3-C20的环烷基、C1-C20的烷氧基、C6-C30芳基、C2-C30杂芳基。
3.根据权利要求1所述的有机化合物，其特征在于，所述Ar1、Ar2、Ar3、Ar4、Ar5至少有一个表示为通式(2)或通式(3)所示结构。
4.根据权利要求1或2所述的有机化合物，其特征在于，所述R1、R2、R3分别独立地表示为甲基、异丙基、叔丁基、金刚烷基、苯基、联苯基、萘基、二甲基芴基、二苯并呋喃基、咔唑基、二苯并噻吩基、吡啶基、萘啶基或咔唑啉基；所述R4表示为为氢原子、氟原子、氰基、甲氧基、甲基、异丙基、叔丁基、金刚烷基、苯基、联苯基、萘基、二甲基芴基、二苯基芴基、螺芴基、二苯并呋喃基、咔唑基、二苯并噻吩基、吡啶基、萘啶基或咔唑啉基。
5.根据权利要求1所述的有机化合物，其特征在于，所述有机化合物的具体结构表示为以下结构中的任一种：
中的任一种。
6.一种有机电致发光器件，包括阴极和阳极，所述阴极和阳极之间设置有有机功能层，其特征在于，所述有机功能层包含有权利要求1-5任一项所述的有机化合物。
7.根据权利要求5所述的一种有机电致发光器件，所述有机功能层包括电子阻挡层或空穴传输层，其特征在于，所述电子阻挡层或空穴传输层含有权利要求1-5任一项所述的有机化合物。
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