CN111662255A - 一种具有高迁移率的有机化合物及其应用 - Google Patents

一种具有高迁移率的有机化合物及其应用 Download PDF

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CN111662255A
CN111662255A CN201910176751.1A CN201910176751A CN111662255A CN 111662255 A CN111662255 A CN 111662255A CN 201910176751 A CN201910176751 A CN 201910176751A CN 111662255 A CN111662255 A CN 111662255A
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梁丽
李崇
吴秀芹
谢丹丹
张兆超
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Jiangsu Sunera Technology Co Ltd
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Abstract

本发明涉及一种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连接有五元并环结构的苯环为核心，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

一种具有高迁移率的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 LightEmission 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。
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器件的发光效率和使用寿命等性能还需要进一步提升。
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。
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，分别为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。
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、电子阻挡层、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括空穴注入材料、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、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：
Figure BDA0001989857320000021
通式(1)中，R1、R2、R3、R4、R5和R6分别独立的表示为氢原子、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、取代或未取代的萘啶基、取代或未取代的吡啶基、通式(2)、通式(3)或通式(4)所示结构；
通式(1)中，R1、R2、R3、R4、R5和R6中至少有一个表示为取代或未取代的萘基、通式(2)或通式(3)所示结构，至少有一个表示为通式(4)所示结构；
通式(1)中，R1、R2、R3、R4、R5和R6中至少有三个不表示为氢原子，R1、R2、R3、R4、R5和R6中至少有两个不表示为氢原子且处于相邻位置；
Figure BDA0001989857320000022
通式(2)、通式(3)和通式(4)中，Z表示为C-R7或N；与其他基团键合的Z表示为C；
X1、X2、X3、X4和X5分别独立地表示为-O-、-S-、-C(R8)(R9)-或-N(R10)-中的任一种；
X2和X3还可表示为单键；
R7、R8、R9和R10分别独立的表示为氢原子、C1-C10烷基、取代或未取代的C6-C30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，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；
上述可取代基团的取代基任选自氰基、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、咔唑基或呋喃基中的一种或多种。
作为本发明的进一步改进，所述有机化合物的结构为以下通式(1-1)-通式(1-5)中的任一种：
Figure BDA0001989857320000023
其中，通式(1-1)～(1-5)中R1、R2、R3、R4、R5和R6具有权利要求1中所述的含义且R1、R2、
R3、R4、R5和R6不表示为氢原子。
作为本发明的进一步改进，所述有机化合物的结构如通式(1-6)所示：
Figure BDA0001989857320000031
通式(1-6)中，R2和R3分别独立的表示为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、取代或未取代的萘啶基、取代或未取代的吡啶基、通式(2)或通式(3)所示结构；
R2和R3中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，所述R7-R10表示为氢原子、甲基、乙基、丙基、异丙基、叔丁基、戊基、取代或未取代的苯基、取代或未取代的吡啶基、取代或未取代的联苯基、取代或未取代的萘基、取代或未取代的萘啶基中的任一种。
作为本发明的进一步改进，所述通式(2)表示为；
Figure BDA0001989857320000032
Figure BDA0001989857320000041
中的任一种。
作为本发明的进一步改进，所述通式(3)表示为；
Figure BDA0001989857320000042
Figure BDA0001989857320000043
中的任一种。
作为本发明的进一步改进，所述通式(4)表示为；
Figure BDA0001989857320000044
Figure BDA0001989857320000051
Figure BDA0001989857320000052
中的任一种。
作为本发明的进一步改进，所述有机化合物的具体结构式为以下结构中的任一种：
Figure BDA0001989857320000053
Figure BDA0001989857320000061
Figure BDA0001989857320000071
Figure BDA0001989857320000081
Figure BDA0001989857320000091
Figure BDA0001989857320000101
Figure BDA0001989857320000111
Figure BDA0001989857320000121
Figure BDA0001989857320000131
Figure BDA0001989857320000141
Figure BDA0001989857320000151
Figure BDA0001989857320000161
Figure BDA0001989857320000171
Figure BDA0001989857320000181
Figure BDA0001989857320000191
Figure BDA0001989857320000192
中的任一种。
本发明的第二个方面是提供一种有机电致发光器件，具有这样的特征，上述有机电致发光器件包括至少一层功能层，上述功能层含有上述有机化合物。
本发明的第三个方面是提供一种有机电致发光器件，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。
本发明的第四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。
Figure BDA0001989857320000201
在250mL三口瓶中，通入氮气，将9.8mol原料G1，11.6mol原料F1，0.3g Pd(dppf)Cl2，30.0mmol醋酸钾加入100mL的1,4-二恶烷中，在130℃下，反应5小时。通过硅胶柱层析分离纯化得到中间体D1，HPLC纯度99.9％，收率63.7％。元素分析结构分子式C27H27BO3：理论值C,79.04；H,6.63；B,2.63；O,11.70；测试值：C,79.05；H,6.64；B,2.62；O,11.69。ESI-MS(m/z)(M+)：理论值为410.21，实测值为410.17。
以中间体D1的合成方法制备中间体D，其中涉及到的原料G和原料F的具体结构如表1所示。
表1
Figure BDA0001989857320000202
Figure BDA0001989857320000211
Figure BDA0001989857320000221
中间体B1的合成：
Figure BDA0001989857320000222
在250mL三口瓶中，通入氮气，将10.0mol原料E1，12.0mol原料F1，0.3g Pd(dppf)Cl2，30.0mmol醋酸钾加入100mL的1,4-二恶烷中，在130℃下，反应5小时。通过硅胶柱层析分离纯化得到中间体B1，HPLC纯度99.8％，收率60.5％。元素分析结构分子式C12H17BO2：理论值C,70.63；H,8.40；B,5.30；O,15.68；测试值：C,70.64；H,8.41；B,5.31；O,15.66。ESI-MS(m/z)(M+)：理论值为204.13，实测值为204.17。
中间体C的合成中应用到的中间体B的制备方法参考中间体B1的制备步骤。
中间体C的合成：
Figure BDA0001989857320000223
具体制备方法如下：称取11.11mol原料A1和7.40mol中间体B1，用体积比为3:1:1的甲苯、水和乙醇混合溶液溶解；再加入0.012mol Pd(OAc)2、7.21mmol Cs2CO3和14.42mmolXphos；在氮气保护、120℃条件下，微波反应3小时。反应结束后，用二氯甲烷萃取得到有机层，再用无水MgSO4干燥，进一步通过柱层析方法分离纯化得到目标产物，HPLC纯度99.8％，收率66％；元素分析结构(分子式C36H24ClN)：理论值C,85.45；H,4.78；Cl,7.01；N,2.77；测试值：C,85.46；H,4.79；Cl,7.00；N,2.79。ESI-MS(m/z)(M+)：理论值为505.16，实测值为505.19。
以中间体C1的合成方法制备中间体C，其中涉及到原料A和中间体B的具体结构如表2所示。
表2
Figure BDA0001989857320000231
Figure BDA0001989857320000241
Figure BDA0001989857320000251
中间体C的制备过程中涉及到的原料A的制备方法参考以下原料A1的合成：
Figure BDA0001989857320000252
具体制备方法如下：
在250mL的三口瓶中，在氮气保护下，加入0.01mol原料M1，0.015mol原料J1，用甲苯和乙醇的混合溶剂溶解(其中甲苯90mL，乙醇45mL)，然后加入含有0.03molNa2CO3水溶液(2M)，通氮气搅拌1h，然后加入0.0001mol Pd(PPh3)4，加热回流15h，取样点板，反应完全。自然冷却、过滤、滤液旋蒸、残余物过硅胶柱，得中间体A-1；HPLC纯度97.7％，收率85.9％；
元素分析结构(分子式C30H19BrClN)：理论值C,70.81；H,3.76；Br,15.70；Cl,6.97；N,2.75；测试值：C,70.82；H,3.77；Br,15.68；Cl,6.96；N,2.77。ESI-MS(m/z)(M+)：理论值为507.04，实测值为507.03。
中间体C3的合成：
Figure BDA0001989857320000261
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A3，0.014mol的原料H1，0.03mol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C3；HPLC纯度98.6％，收率86.5％；元素分析结构(分子式C42H32ClN)：理论值C,86.06；H,5.50；Cl,6.05；N,2.39；测试值：C,86.07；H,5.51；Cl,6.03；N,2.39。ESI-MS(m/z)(M+)：理论值为585.22，实测值为585.25。
以中间体C3的合成方法制备中间体C，其中涉及到原料A和原料H具体结构如表3所示。
表3
Figure BDA0001989857320000262
Figure BDA0001989857320000271
目标化合物的制备反应方程式如下所示：
Figure BDA0001989857320000272
(1)称取原料A和中间体B，用体积比为3:1:1的甲苯/水/乙醇混合溶液溶解，再加入乙酸钯、碳酸铯和2-二环己基磷-2',4',6'-三异丙基联苯；在氮气保护、120℃条件下，微波反应3小时，反应结束后，用二氯甲烷萃取得到有机层，再用无水MgSO4干燥，进一步通过柱层析方法分离纯化得到中间体C；
(2)称取中间体C和中间体D，用体积比为3:1:1的甲苯/水/乙醇混合溶液溶解，再加入乙酸钯、碳酸铯和2-二环己基磷-2',4',6'-三异丙基联苯；在氮气保护、120℃条件下，微波反应3小时，反应结束后，用二氯甲烷萃取得到有机层，再用无水MgSO4干燥，进一步通过柱层析方法分离纯化得到目标产物；
所述原料A和中间体B的摩尔比为1.0～3.0:1，中间体C和中间体D的摩尔比为1.0～3.0:1，Pd(OAc)2与原料A的摩尔比为0.001～0.003:1，Cs2CO3与原料A的摩尔比为0.5～3:1，Xphos与原料A摩尔比为1.0～4:1。Pd(OAc)2与中间体C的摩尔比为0.001～0.003:1，Cs2CO3与中间体C的摩尔比为0.5～3:1，Xphos与中间体C摩尔比为1.0～4:1。
目标化合物的制备反应方程式也可如下所示：
Figure BDA0001989857320000273
具体制备方法如下：250ml的三口瓶，在通入氮气的气氛下，加入原料A、原料H、叔丁醇钾、Pd2(dba)3、三苯基膦及溶剂甲苯，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，得到中间体C；
所述原料A和原料H的摩尔比为1.0～3.0:1，叔丁醇钾与原料H的摩尔比为1～5:1，Pd2(dba)3与原料H的摩尔比为0.01～0.03:1，三苯基膦与原料H摩尔比为0.01～0.03:1；
Figure BDA0001989857320000281
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J、叔丁醇钾、Pd2(dba)3、三苯基膦及溶剂甲苯，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；
所述中间体C和原料J的摩尔比为1.0～3.0:1，叔丁醇钾与原料J的摩尔比为1～5:1，Pd2(dba)3与原料J的摩尔比为0.01～0.03:1，三苯基膦与原料J摩尔比为0.01～0.03:1。
制备实施例1：化合物6的合成：
Figure BDA0001989857320000282
具体制备方法如下：称取11.11mol中间体C1和7.40mol中间体D1，用体积比为3:1:1的甲苯/水/乙醇混合溶液溶解；再加入0.012molPd(OAc)2、7.21mmol Cs2CO3和14.42mmolXphos；在氮气保护、120℃条件下，微波反
应3小时。反应结束后，用二氯甲烷萃取得到有机层，再用无水MgSO4干燥，进一步通过柱层析方法分离纯化得到目标产物，HPLC纯度99.8％，收率66％。
元素分析结构(分子式C57H39NO)：理论值C,90.81；H,5.21；N,1.86；O,2.12；测试值：C,90.82；H,5.22；N,1.87；O,2.10。ESI-MS(m/z)(M+)：理论值为753.30，实测值为753.25。
其余目标化合物的涉及到的反应类型和化合物6的制备步骤涉及到的反应类型相同。
制备实施例2：化合物20的合成：
Figure BDA0001989857320000283
制备实施例3：化合物30的合成：
Figure BDA0001989857320000284
制备实施例4：化合物33的合成：
Figure BDA0001989857320000291
制备实施例5：化合物52的合成：
Figure BDA0001989857320000292
制备实施例6：化合物88的合成：
Figure BDA0001989857320000293
制备实施例7：化合物113的合成：
Figure BDA0001989857320000294
制备实施例8：化合物132的合成：
Figure BDA0001989857320000295
制备实施例9：化合物149的合成：
Figure BDA0001989857320000301
制备实施例10：化合物162的合成：
Figure BDA0001989857320000302
制备实施例11：化合物176的合成：
Figure BDA0001989857320000303
制备实施例12：化合物189的合成：
Figure BDA0001989857320000304
制备实施例13：化合物204的合成：
Figure BDA0001989857320000305
制备实施例14：化合物216的合成：
Figure BDA0001989857320000306
制备实施例15：化合物231的合成：
Figure BDA0001989857320000311
制备实施例16：化合物246的合成：
Figure BDA0001989857320000312
制备实施例17：化合物248的合成：
Figure BDA0001989857320000313
制备实施例19：化合物257的合成：
Figure BDA0001989857320000314
制备实施例20：化合物259的合成：
Figure BDA0001989857320000315
制备实施例21：化合物261的合成：
Figure BDA0001989857320000316
制备实施例22：化合物284的合成：
Figure BDA0001989857320000321
制备实施例23：化合物304的合成：
Figure BDA0001989857320000322
制备实施例24：化合物342的合成：
Figure BDA0001989857320000323
制备实施例25：化合物366的合成：
Figure BDA0001989857320000324
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4所示。
表4
Figure BDA0001989857320000325
Figure BDA0001989857320000331
Figure BDA0001989857320000341
Figure BDA0001989857320000351
制备实施例18：化合物252的合成：
Figure BDA0001989857320000352
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中间体C18，0.014mol的原料J1，0.03mol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；HPLC纯度98.6％，收率86.5％；
元素分析结构(分子式C67H42N2O)：理论值C,90.31；H,4.75；N,3.14；O,1.80；测试值：C,90.32；H,4.76；N,3.14；O,1.78。ESI-MS(m/z)(M+)：理论值为890.33，实测值为890.25。
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。对本发明化合物及现有材料分别进行热性能、T1能级、Eg、HOMO能级以及空穴迁移率的测试，结果如表5所示。
表5
Figure BDA0001989857320000361
Figure BDA0001989857320000371
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能级是由光电子发射谱仪(AC-2型PESA)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：将材料制作成单电荷器件，用SCLC方法测定。使用为Gaussian16、使用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|；Eg实测通过紫外光谱进行测试。
由上表数据可知，本发明化合物具有适当的HOMO能级，适合作为空穴传输层和电子阻挡层材料；较高的带隙宽度(Eg)，保证材料在可见光领域范围内没有吸收。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1～30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2～30、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2～11中空穴传输层的材料发生了改变；器件实施例12～30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6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6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。
相关现有材料的结构如下所示：
Figure BDA0001989857320000381
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7示。
表6
Figure BDA0001989857320000382
Figure BDA0001989857320000391
Figure BDA0001989857320000401
表7
Figure BDA0001989857320000402
Figure BDA0001989857320000411
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；寿命测试系统为日本System Engineer's Co.,LTD开发的型号为EAS-62C的OLED器件寿命测试仪。
表7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、12、25和器件比较例1在-10～80℃区间进行效率测试，所得结果如表8和图2所示。
表8
Figure BDA0001989857320000412
从表8的数据可知，实施例1、12、25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 (10)

1.一种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：
Figure FDA0001989857310000011
通式(1)中，R1、R2、R3、R4、R5和R6分别独立的表示为氢原子、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、取代或未取代的萘啶基、取代或未取代的吡啶基、通式(2)、通式(3)或通式(4)所示结构；
通式(1)中，R1、R2、R3、R4、R5和R6中至少有一个表示为取代或未取代的萘基、通式(2)或通式(3)所示结构，至少有一个表示为通式(4)所示结构；
通式(1)中，R1、R2、R3、R4、R5和R6中至少有三个不表示为氢原子，R1、R2、R3、R4、R5和R6中至少有两个不表示为氢原子且处于相邻位置；
Figure FDA0001989857310000012
通式(2)、通式(3)和通式(4)中，Z相同或不同的表示为C-R7或N；与其他基团键合的Z表示为C；
X1、X2、X3、X4和X5分别独立地表示为-O-、-S-、-C(R8)(R9)-或-N(R10)-中的任一种；
X2和X3还可表示为单键；
R7、R8、R9和R10分别独立的表示为氢原子、C1-C10烷基、取代或未取代的C6-C30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，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；
上述可取代基团的取代基任选自氰基、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，所述有机化合物的结构为以下通式(1-1)-通式(1-5)中的任一种：
Figure FDA0001989857310000013
其中，通式(1-1)～(1-5)中R1、R2、R3、R4、R5和R6具有权利要求1中所述的含义，且R1、R2、R3、R4、R5和R6不表示为氢原子。
3.根据权利要求1所述的有机化合物，其特征在于，所述有机化合物的结构如通式(1-6)所示：
Figure FDA0001989857310000021
通式(1-6)中，R2和R3分别独立的表示为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、取代或未取代的萘啶基、取代或未取代的吡啶基、通式(2)或通式(3)所示结构；
R2和R3中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所述的有机化合物，其特征在于，所述R7-R10分别独立的表示为氢原子、甲基、乙基、丙基、异丙基、叔丁基、戊基、取代或未取代的苯基、取代或未取代的吡啶基、取代或未取代的联苯基、取代或未取代的萘基、取代或未取代的萘啶基中的任一种。
5.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)表示为；
Figure FDA0001989857310000022
Figure FDA0001989857310000031
中的任一种。
6.根据权利要求1所述的有机化合物，其特征在于，所述通式(3)表示为：
Figure FDA0001989857310000032
Figure FDA0001989857310000033
中的任一种。
7.根据权利要求1所述的有机化合物，其特征在于，所述通式(4)表示为；
Figure FDA0001989857310000034
Figure FDA0001989857310000041
Figure FDA0001989857310000042
中的任一种。
8.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式为以下结构中的任一种：
Figure FDA0001989857310000043
Figure FDA0001989857310000051
Figure FDA0001989857310000061
Figure FDA0001989857310000071
Figure FDA0001989857310000081
Figure FDA0001989857310000091
Figure FDA0001989857310000101
Figure FDA0001989857310000111
Figure FDA0001989857310000121
Figure FDA0001989857310000131
Figure FDA0001989857310000141
Figure FDA0001989857310000151
Figure FDA0001989857310000161
Figure FDA0001989857310000171
Figure FDA0001989857310000181
Figure FDA0001989857310000182
中的任一种。
9.一种有机电致发光器件，其特征在于，所述有机电致发光器件包括至少一层功能层含有权利要求1-8任一项所述的有机化合物。
10.根据权利要求9所述的一种有机电致发光器件，所述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1-8任一项所述的有机化合物。
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CN105051035A (zh) * 2013-06-13 2015-11-11 第一毛织株式会社 有机化合物、有机光电装置和显示装置
CN110272427A (zh) * 2018-03-14 2019-09-24 江苏三月光电科技有限公司 一种以芴为核心的化合物、其制备方法及其在有机电致发光器件上的应用

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CN110272427A (zh) * 2018-03-14 2019-09-24 江苏三月光电科技有限公司 一种以芴为核心的化合物、其制备方法及其在有机电致发光器件上的应用

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