CN111362813A - 一种以三芳胺为核心的化合物及其应用 - Google Patents

一种以三芳胺为核心的化合物及其应用 Download PDF

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CN111362813A
CN111362813A CN201811598387.XA CN201811598387A CN111362813A CN 111362813 A CN111362813 A CN 111362813A CN 201811598387 A CN201811598387 A CN 201811598387A CN 111362813 A CN111362813 A CN 111362813A
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李崇
张小庆
赵四杰
王芳
谢丹丹
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Jiangsu Sunera Technology Co Ltd
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Abstract

本发明公开了一种以三芳胺为核心的化合物及其应用，属于半导体技术领域。本发明提供的化合物的结构如通式(1)所示：
Figure DDA0001921865220000011
本发明提供的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，较高迁移率，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

一种以三芳胺为核心的化合物及其应用
技术领域
本发明涉及一种以三芳胺为核心的化合物及其应用，属于半导体技术领域。
背景技术
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，本发明申请人提供了一种以三芳胺为核心的化合物及其应用，本发明化合物有很强的空穴传输能力，能够提高有机电致发光器件的效率。
本发明的技术方案如下：
一种以三芳胺为核心的化合物，所述合物的结构如通式(1)所示：
Figure BDA0001921865200000021
通式(1)中R表示为氢原子、氰基、卤素、C1-C10直链烷基、C3-C10的支链烷基、取代或未取代的C6-30芳基、含有一个或多个杂原子的取代或未取代的5～30元杂芳基中的一种；R可以取代通式(1)结构中的任意可取代位点；
a表示为数字0、1、2、3或4；
其中X可表示为
Figure BDA0001921865200000022
-O-、-S-、-C(R5)(R6)-或-N(R7)-；
其中R1、R2、R3和R4可以表示为氢或者通式(2)的结构，且R1、R2、R3和R4不同时表示为氢原子,当X表示为
Figure BDA0001921865200000023
时，R1，R2不同时表示为氢
Figure BDA0001921865200000024
通式(2)中Ar1、Ar2可分别独立的表示为-L1-R8；L和L1分别独立地表示为单键、取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的亚二联苯基、取代或未取代的亚三联苯基、取代或未取代的亚吡啶基、取代或未取代的亚萘啶基；R8表示为取代或未取代的苯基、取代或未取代的萘基、取代或未取代的二联苯基、取代或未取代的三联苯基、取代或未取代的吡啶基、取代或未取代的萘啶基、取代或未取代的氮杂苯或通式(3)所示结构；
Figure BDA0001921865200000025
通式(3)中所述X1、X2分别独立的表示为单键、-O-、-S-、-C(R9)(R10)-或-N(R11)-，X1、X2不同时表示为单键；
所述Z表示为氮原子或C(R12)；
所述R5～R7,R9～R11分别独立的表示为C1-20的烷基、取代或未取代的C6-30芳基、含有一个或多个杂原子的取代或未取代的5～30元杂芳基中的一种；其中R5与R6、R9与R10可相互连接成环；
所述R12表示为氢原子、氕、氘、氚、氰基、卤素原子、C1-20的烷基、C2-20的烯烃基、取代或未取代的C6-30芳基、含有一个或多个杂原子的取代或未取代的5～30元杂芳基中的一种；相互两个或多个R12可相互连接成环；
所述可取代基团的取代基任选自氕、氘、氚、氰基、卤素、C1-20的烷基、C6-30芳基、含有一个或多个杂原子的5～30元杂芳基中的一种或多种；
所述杂原子任选自氧原子、硫原子或氮原子中的一种或多种。
优选方案，所述R表示为氢原子、氟原子、氰基、甲基、乙基、丙基、异丙基、丁基、叔丁基、戊基、取代或未取代的苯基、取代或未取代的二联苯基、取代或未取代的三联苯基、取代或未取代的萘基、取代或未取代的吡啶基、取代或未取代的二苯呋喃基、取代或未取代的萘啶基、取代或未取代的咔唑基；
所述R5～R7、R9～R11分别独立的表示为甲基、乙基、丙基、异丙基、丁基、叔丁基、戊基、苯基、二联苯基、三联苯基、萘基、吡啶基或呋喃基；
所述R12分别独立的表示为氢原子、氕、氘、氚、氟原子、氰基、甲基、乙基、丙基、异丙基、丁基、叔丁基、戊基、取代或未取代的苯基、取代或未取代的二联苯基、取代或未取代的三联苯基、取代或未取代的萘基、取代或未取代的吡啶基、取代或未取代的二苯呋喃基、取代或未取代的萘啶基、取代或未取代的咔唑基；
所述可取代基团的取代基任选自氕、氘、氚、氟原子、氰基、甲基、乙基、丙基、异丙基、丁基、叔丁基、戊基、苯基、二联苯基、三联苯基、萘基、吡啶基、萘啶基、二苯呋喃基或咔唑基中的一种或多种。
优选方案，所述通式(1)可表述为通式(1-1)至通式(1-5)所表述结构：
Figure BDA0001921865200000041
进一步的，所述通式(2)中，所述Ar1、Ar2可表示为以下结构：
Figure BDA0001921865200000042
优选方案，所述R3和R4表示为氢原子，R1和R2至少有一个表示为通式(2)所示结构。进一步的，所述的化合物可表示以下结构中的任一种：
Figure BDA0001921865200000051
Figure BDA0001921865200000061
Figure BDA0001921865200000071
Figure BDA0001921865200000081
Figure BDA0001921865200000091
Figure BDA0001921865200000101
Figure BDA0001921865200000111
Figure BDA0001921865200000121
Figure BDA0001921865200000131
Figure BDA0001921865200000141
Figure BDA0001921865200000151
Figure BDA0001921865200000161
Figure BDA0001921865200000171
Figure BDA0001921865200000181
一种有机电致发光器件，所述有机电致发光器件至少一层功能层含有所述以三芳胺结构为核心的化合物。
一种有机电致发光器件，所述三芳胺为核心的化合物作为空穴传输层或者电子阻挡层材料，用于制作有机电致发光器件。
一种照明或显示元件，所述元件包含所述的有机电致发光器件。
另外说明，本发明申请C1-20烷基优选下列基团：甲基、乙基、正丙基、异丙基、正丁基、异丁基、1-甲基丙基、叔丁基、正戊基、异戊基、1-乙基丙基、1-甲基丁基、2-甲基丁基、3-甲基丁基、正己基、1-甲基戊基、2-甲基戊基、3-甲基戊基、4-甲基戊基、3,3-二甲基丁基、1-乙基丁基、2-乙基丁基。
在本发明的上下文中，杂芳基为单环或双环芳族杂环(杂芳族)，其含有最多达四个选自N、O和S的相同或不同的环杂原子，并且经由环碳原子或如果合适，经由环氮原子连接，优选下列基团：呋喃基、吡咯基、噻吩基、吡唑基、咪唑基、喹啉基、噻唑基、噁唑基、异噁唑基、异噻唑基、三唑基、噁二唑基、噻二唑基、四唑基、吡啶基、嘧啶基、哒嗪基、吡嗪基和三嗪基。
当本发明化合物中的基团被取代时，所述基团可被单取代或多取代，除非另有说明。
本发明有益的技术效果在于：
本发明化合物中的p-π共轭效应使得其有很强的空穴传输能力，高的空穴传输速率能够提高有机电致发光器件的效率；化合物中不对称的三芳胺结构能够降低分子的结晶性，降低分子的平面性，阻止分子在平面上移动从而提高了分子的热稳定性。本发明的化合物中的螺旋蒽含有大面积的共轭，连接含氮的支链，该结构具有较高的介电常数，使化合物具有较高的折射率。
本专利发明化合物具有高的空穴迁移率，使得电子和空穴在发光层的分布更加平衡，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，提升激子在发光层中的复合效率；
本发明的化合物在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，各标号所代表的部件如下：
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、发光层，7、空穴阻挡/电子传输层，8、电子注入层，9、阴极层，10、光取出层。
图2为本发明OLED器件在不同温度下测量的效率曲线图。
具体实施方式
以下结合附图对本发明的原理和特征进行描述，所举实例只用于解释本发明，并非用于限定本发明的范围。
下述实施例中所有反应物均采购于中节能万润精细化工股份有限公司。
实施例1化合物2的合成
Figure BDA0001921865200000191
将0.01mol反应物I-1和0.012mol反应物II-1溶解于150mL甲苯中，加入0.015mol的叔丁醇钾，以及0.0001mol的在氮气的氛围下120℃反应24小时，取样点板，待反应完全后，冷却、过滤，将滤液旋蒸除去溶剂，粗产品过硅胶柱，得到化合物2，HPLC纯度99.26％，收率76.95％；元素分析结构(C55H35N)理论值：C,93.06；H,4.97；N,1.97；测试值：C,93.03；H,4.98；N,1.99。HRMS(EI)：理论值：709.2770，实测值：709.2724。
实施例8化合物115的合成
Figure BDA0001921865200000201
将0.01mol反应物I-2和0.012mol反应物II-6溶解于150mL甲苯/乙醇(V甲苯：V乙醇＝5：1)混合溶液中，除氧后加入0.0002mol Pd(PPh3)4和0.02mol K2CO3，在通入氮气的气氛下110℃反应24个小时，取样点板，待反应物反应完全后，冷却、过滤，将滤液旋蒸除去溶剂，粗产品过硅胶柱，得到化合物115；HPLC纯度98.97％，收率74.5％；元素分析结构(C68H51N)理论值：C,92.58；H,5.83；N,1.59；测试值：C,92.58；H,5.84；N,1.58。HRMS(EI)：理论值：881.4022，实测值：881.4098。
重复实施例1或者实施例8的制备过程合成以下化合物；其中反应条件I表示制备过程与实施例1相同；反应条件II表示制备过程与实施例8相同；不同之处在于使用下表1中所列出的反应物I和反应物II。
表1
Figure BDA0001921865200000202
Figure BDA0001921865200000211
Figure BDA0001921865200000221
Figure BDA0001921865200000231
反应实施例中的反应物I的合成步骤如下：
Figure BDA0001921865200000232
用50-80mL干燥的THF溶解原料II，在-78℃下保温30min后，在氮气的氛围下加入1.2M-1.5M的正丁基锂溶液,所述原料II与正丁基锂的摩尔比为1:(0.8-1.1)，搅拌1至2小时后，在氮气的氛围下继续加入原料I，其中中间体I与原料I的摩尔比为1：(0.8-1.2)，搅拌均匀后缓慢升至室温，在室温继续搅拌反应10～24小时后，向反应体系总加入20-30mL的水，继续搅拌1-2小时，产物从反应体系中析出，过滤，得到中间产物；将上述中间产物溶于乙酸和盐酸的混合液中，其中乙酸和盐酸的体积比为100:(8-10),搅拌加热至110℃，反应12h，自然冷却至室温，产物析出，过滤用水和甲醇洗涤得到反应物I；根据该合成路线具体的原料与合成的反应物I如下表2所示
表2
Figure BDA0001921865200000241
Figure BDA0001921865200000251
上述表格中所述原料II的合成方法
当X表示为
Figure BDA0001921865200000252
时，具体的合成步骤如原料II-1的合成方法：
Figure BDA0001921865200000253
步骤1：将0.011mol 1,8二溴萘以及0.01mol 2-甲酰基苯基硼酸溶于100mL甲苯:乙醇＝3:1的混合溶剂中，在氮气的保护下加入2M的K2CO3水溶液10mL以及0.0002mol的Pd(PPh3)4，在110℃下反应24小时后，取样点板，待反应物反应完全后，冷却、过滤，将滤液旋蒸除去溶剂，粗产品过硅胶柱，得到中间体1-1；HPLC纯度98.97％，收率84.5％；HRMS(EI)：理论值：309.9993，实测值：309.9938。
步骤2：将0.01mol中间体I-1溶于60mL四氢呋喃中，在0℃，加入叔丁基钾0.02mol和甲氧基甲基三苯基氯化磷0.01mol，在氮气的氛围下升至室温搅拌反应24小时后，取样点板，待反应物反应完全后，出去溶剂，加入二氯甲烷50mL溶解后加入甲磺酸0.01mol，室温搅拌2h后，过滤，将滤液旋蒸除去溶剂，粗产品过硅胶柱，得到原料II-1；HPLC纯度97.5％，收率65％；HRMS(EI)：理论值：306.0044，实测值：306.0047。
当X表示为-C(R5)(R6)-时，具体的合成步骤如原料II-3的合成方法
Figure BDA0001921865200000254
步骤1：将0.011mol 1,8二溴萘以及0.01mol2-甲氧羰苯硼酸溶于100mL甲苯:乙醇＝3:1的混合溶剂中，在氮气的保护下加入2M的K2CO3水溶液10mL以及0.0002mol的Pd(PPh3)4，在110℃下反应24小时后，取样点板，待反应物反应完全后，冷却、过滤，将滤液旋蒸除去溶剂，粗产品过硅胶柱，得到中间体1-2；HPLC纯度96.97％，收率88.5％；HRMS(EI)：理论值：340.0099，实测值：340.0018。
步骤2：将干燥的0.012mol的镁和0.012mol的碘甲烷放入10mL的无水乙醚中，于40℃下反应搅拌1h，待Mg消失后，将温度降至室温得到CH3-Mg-I；将干燥的0.01mol中间体I-2溶于40mL的无水乙醚中冷却至0℃，在氮气的氛围下向反应液中滴加CH3-Mg-I，缓慢升至室温反应搅拌后，加入稀盐酸水溶液猝灭反应，过滤，将滤液旋蒸除去溶剂后，在0℃下向反应瓶中加入50mL的醋酸和3mL的磷酸，升温至室温搅拌反应2小时，带反应结束；将反应至于0℃冰浴中，加入氢氧化钠水溶液调节PH值至7；过滤，将滤液旋蒸除去溶剂，粗产品过硅胶柱，得到原料II-3；HPLC纯度97.5％，收率65％；HRMS(EI)：理论值：322.0357，实测值：322.0354。
当X表示为氧原子或者硫原子时，具体的合成步骤如原料II-6的合成方法
Figure BDA0001921865200000261
步骤1：将0.011mol 1,8二溴萘以及0.01mol2-甲氧基苯硼酸溶于100mL甲苯:乙醇＝3:1的混合溶剂中，在氮气的保护下加入2M的K2CO3水溶液10mL以及0.0002mol的Pd(PPh3)4，在110℃下反应24小时后，取样点板，待反应物反应完全后，冷却、过滤，将滤液旋蒸除去溶剂，粗产品过硅胶柱，得到中间体1-3；HPLC纯度96.97％，收率88.5％；HRMS(EI)：理论值：313.0150，实测值：313.0119。
步骤2：将0.01mol中间体1-3，溶于60mL的无水DMF中，加入0.025mol的碳酸铯，在氮气的氛围下升温至60℃，反应3小时后，取样点板，待反应物反应完全后，冷却、过滤，将滤液旋蒸除去溶剂，粗产品过硅胶柱，得到原料II-6；HPLC纯度95.50％，收率74.5％；HRMS(EI)：理论值：295.9837，实测值：295.9825。
当X表示为-N(R7)-时，具体的合成步骤如原料II-4的合成方法
Figure BDA0001921865200000262
将0.01mol的1-溴苯并咔唑和0.012mol的溴苯溶于60mL的甲苯中，加入0.02mol的叔丁醇钾和0.0002mol的醋酸钯，在氮气的氛围内加热至120℃反应24小时后，取样点板，待反应物反应完全后，冷却、过滤，将滤液旋蒸除去溶剂，粗产品过硅胶柱，得到中间体II-4；HPLC纯度96.50％，收率86.5％；HRMS(EI)：理论值：371.0310，实测值：371.0315。
本发明的有机化合物在发光器件中使用，可以作为空穴传输层材料使用。对本发明化合物2、化合物11、化合物44、化合物46、化合物65、化合物73、化合物99、化合物115、化合物134、化合物146、化合物156、化合物174、化合物184、化合物189、化合物192、化合物200、化合物209、化合物227、化合物240、化合物246、化合物257分别进行T1能级、热性能、HOMO能级的测试，检测结果如表3所示。
表3
Figure BDA0001921865200000271
Figure BDA0001921865200000281
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/mL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；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；最高占据分子轨道HOMO能级是由电离能量测试系统(IPS3)测试，测试为大气环境。空穴迁移率：将材料制作成单电荷器件，用SCLC方法测定。
由上表数据可知，本发明的有机化合物具有高的玻璃转化温度，可提高材料膜相态稳定性，进一步提高器件使用寿命；合适的HOMO能级可以解决载流子的注入问题，可降低器件电压；较高的空穴迁移率，可以提升效效率以及拉长寿命。本发明以三芳胺为核心的化合物在应用于OLED器件的不同功能层后，可有效提高器件的发光效率及使用寿命。
以下通过器件实施例1-18和器件比较例1详细说明本发明合成的化合物在器件中作为空穴传输材料的应用效果。器件实施例2-18以及器件比较例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，所不同的是器件中空穴传输层或电子阻挡层材料发生了改变。器件叠层结构如表4所示，各器件的性能测试结果见表5和表6。
器件实施例1
透明基板层1/ITO阳极层2/空穴注入层3(HAT-CN，厚度10nm)/空穴传输层4(化合物2，厚度60nm)/电子阻挡层5(EB-1，厚度20nm)/发光层6(GH1、GH2和GD-1按照45:45:10的重量比混掺，厚度40nm)/空穴阻挡/电子传输层7(ET-1和Liq，按照1:1的重量比混掺，厚度40nm)/电子注入层8(LiF，厚度1nm)/阴极层9(Mg和Ag，按照9:1的重量比混掺，厚度15nm)/CPL层10(化合物CP-1，厚度70nm)。
具体制备过程如下：
如图1所示，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2作为空穴传输层4。随后蒸镀20nm厚度的EB-1作为电子阻挡层5。上述空穴传输材料蒸镀结束后，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40nm，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。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以及器件的寿命。
按照上述步骤完成电致发光器件的制作后，测量器件的IVL数据和光衰寿命，其结果见表5所示。相关材料的分子结构式如下所示：
Figure BDA0001921865200000291
表4
Figure BDA0001921865200000292
Figure BDA0001921865200000301
Figure BDA0001921865200000311
各器件实施例和器件比较例1的效率和寿命数据见表5所示。
表5
编号 电流效率(cd/A) 色彩 LT97寿命(Hr)@5000nits
器件实施例1 123.4 绿光 121.6
器件实施例2 121.5 绿光 119.7
器件实施例3 125.3 绿光 126.0
器件实施例4 124.0 绿光 116.6
器件实施例5 126.3 绿光 120.4
器件实施例6 129.0 绿光 123.1
器件实施例7 125.6 绿光 121.4
器件实施例8 125.6 绿光 118.3
器件实施例9 121.2 绿光 119.7
器件实施例10 124.0 绿光 126.9
器件实施例11 123.1 绿光 120.0
器件实施例12 128.2 绿光 125.2
器件实施例13 121.2 绿光 121.9
器件实施例14 128.3 绿光 118.9
器件实施例15 129.1 绿光 122.6
器件实施例16 128.5 绿光 121.5
器件实施例17 120.0 绿光 123.4
器件实施例18 120.4 绿光 121.9
比较例1 116 绿光 80.5
注：LT97指的是在电流密度为10mA/cm2情况下，器件亮度衰减到97％所用时间；
寿命测试系统为韩国脉冲科学M600型OLED器件寿命测试仪。
由表5器件数据结果可以看出，本发明的有机发光器件无论是在效率还是寿命均相对于已知材料的OLED器件获得较大的提升。
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、7、16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
Figure BDA0001921865200000321
从表6和图2的数据可知，器件实施例1、7、16为本发明材料和已知材料搭配的器件结构，与器件比较例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。
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 (9)

1.一种以三芳胺为核心的化合物，其特征在于，该化合物的结构如通式(1)所示：
Figure FDA0001921865190000011
通式(1)中R表示为氢原子、氰基、卤素、C1-C10直链烷基、C3-C10的支链烷基、取代或未取代的C6-30芳基、含有一个或多个杂原子的取代或未取代的5～30元杂芳基中的一种；R可以取代通式(1)结构中的任意可取代位点；
a表示为数字0、1、2、3或4；
其中X表示为
Figure FDA0001921865190000012
-O-、-S-、-C(R5)(R6)-或-N(R7)-；
其中R1、R2、R3和R4表示为氢或者通式(2)的结构，且R1、R2、R3和R4不同时表示为氢原子,当X表示为
Figure FDA0001921865190000013
时，R1，R2不同时表示为氢。
Figure FDA0001921865190000014
通式(2)中Ar1、Ar2分别独立的表示为-L1-R8；L和L1分别独立地表示为单键、取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的亚二联苯基、取代或未取代的亚三联苯基、取代或未取代的亚吡啶基、取代或未取代的亚萘啶基；R8表示为取代或未取代的苯基、取代或未取代的萘基、取代或未取代的二联苯基、取代或未取代的三联苯基、取代或未取代的吡啶基、取代或未取代的萘啶基、取代或未取代的氮杂苯或通式(3)所示结构；
Figure FDA0001921865190000015
通式(3)中所述X1、X2分别独立的表示为单键、-O-、-S-、-C(R9)(R10)-或-N(R11)-，X1、X2不同时表示为单键；
所述Z表示为氮原子或C(R12)；
所述R5～R7，R9～R11分别独立的表示为C1-20的烷基、取代或未取代的C6-30芳基、含有一个或多个杂原子的取代或未取代的5～30元杂芳基中的一种；其中R5与R6、R9与R10可相互连接成环；
所述R12表示为氢原子、氕、氘、氚、氰基、卤素原子、C1-20的烷基、C2-20的烯烃基、取代或未取代的C6-30芳基、含有一个或多个杂原子的取代或未取代的5～30元杂芳基中的一种；相互两个或多个R12可相互连接成环；
所述可取代基团的取代基任选自氕、氘、氚、氰基、卤素、C1-20的烷基、C6-30芳基、含有一个或多个杂原子的5～30元杂芳基中的一种或多种；
所述杂原子任选自氧原子、硫原子或氮原子中的一种或多种。
2.根据权利要求1所述的化合物，其特征在于，所述R表示为氢原子、氟原子、氰基、甲基、乙基、丙基、异丙基、丁基、叔丁基、戊基、取代或未取代的苯基、取代或未取代的二联苯基、取代或未取代的三联苯基、取代或未取代的萘基、取代或未取代的吡啶基、取代或未取代的二苯呋喃基、取代或未取代的萘啶基、取代或未取代的咔唑基；
所述R5～R7、R9～R11分别独立的表示为甲基、乙基、丙基、异丙基、丁基、叔丁基、戊基、苯基、二联苯基、三联苯基、萘基、吡啶基或呋喃基；
所述R12表示为氢原子、氕、氘、氚、氟原子、氰基、甲基、乙基、丙基、异丙基、丁基、叔丁基、戊基、取代或未取代的苯基、取代或未取代的二联苯基、取代或未取代的三联苯基、取代或未取代的萘基、取代或未取代的吡啶基、取代或未取代的二苯呋喃基、取代或未取代的萘啶基、取代或未取代的咔唑基；
所述可取代基团的取代基任选自氕、氘、氚、氟原子、氰基、甲基、乙基、丙基、异丙基、丁基、叔丁基、戊基、苯基、二联苯基、三联苯基、萘基、吡啶基、萘啶基、二苯呋喃基或咔唑基中的一种或多种。
3.根据权利要求1所述的化合物，所述通式(1)可表述为通式(1-1)-通式(1-5)所表述结构：
Figure FDA0001921865190000031
4.根据权利要求1所述的化合物,通式(2)中，所述Ar1、Ar2可表示为以下结构：
Figure FDA0001921865190000032
5.根据权利要求1所述的化合物，其特征在于，所述R3和R4表示为氢原子，R1和R2至少有一个表示为通式(2)所示结构。
6.根据权利要求1所述的化合物，通式(1)可表示以下结构中的任一种：
Figure FDA0001921865190000041
Figure FDA0001921865190000051
Figure FDA0001921865190000061
Figure FDA0001921865190000071
Figure FDA0001921865190000081
Figure FDA0001921865190000091
Figure FDA0001921865190000101
Figure FDA0001921865190000111
Figure FDA0001921865190000121
Figure FDA0001921865190000131
Figure FDA0001921865190000141
Figure FDA0001921865190000151
Figure FDA0001921865190000161
7.一种有机电致发光器件，其特征在于，至少一层功能层含有权利要求1-6所述的以三芳胺为核心的化合物。
8.根据权利要求7所述的一种有机电致发光器件，包含空穴传输层或电子阻挡层，其特征在于，所述空穴传输层或电子阻挡层含有权利要求1-6所述的以三芳胺为核心的化合物。
9.一种照明或显示元件，其特征在于，包括如权利要求7或8所述的有机电致发光器件。
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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113429374A (zh) * 2021-06-30 2021-09-24 昆山国显光电有限公司 一种螺苯并蒽芴类化合物、有机电致发光器件及显示面板
CN114075117A (zh) * 2021-06-04 2022-02-22 陕西莱特迈思光电材料有限公司 一种有机化合物以及使用其的电子元件和电子装置
KR20220086363A (ko) * 2020-12-16 2022-06-23 엘티소재주식회사 헤테로 고리 화합물, 이를 포함하는 유기 발광 소자, 이의 제조방법 및 유기물층용 조성물
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Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107840834A (zh) * 2016-09-20 2018-03-27 北京鼎材科技有限公司 一种苯并芘类化合物及应用

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107840834A (zh) * 2016-09-20 2018-03-27 北京鼎材科技有限公司 一种苯并芘类化合物及应用

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