CN113896741A - 含硼氮配位键的螺结构化合物及其作为发光层的有机电致发光器件 - Google Patents

含硼氮配位键的螺结构化合物及其作为发光层的有机电致发光器件 Download PDF

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CN113896741A
CN113896741A CN202111330137.XA CN202111330137A CN113896741A CN 113896741 A CN113896741 A CN 113896741A CN 202111330137 A CN202111330137 A CN 202111330137A CN 113896741 A CN113896741 A CN 113896741A
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张佐伦
叶建江
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Abstract

一种含硼氮配位键的螺结构化合物及其作为发光层的有机电致发光器件，属于有机电致发光技术领域。本发明所述的一种含硼氮配位键的螺结构化合物，其结构通式如(1)或(2)所示，其不仅可以用作发光层的掺杂材料，还可以直接用作非掺杂的发光层材料应用于OLED器件中。由该化合物制备的器件表现出了高亮度、高效率的优点，同时器件在高亮度下具有较小的效率滚降，从而表明该含硼氮配位键的螺结构化合物是一种优秀的有机电致发光材料。

Description

含硼氮配位键的螺结构化合物及其作为发光层的有机电致发 光器件
技术领域
本发明属于有机电致发光技术领域，具体涉及一种含硼氮配位键的螺结构化合物及其作为发光层的有机电致发光器件。
背景技术
进入21世纪以来，显示在人们的社会生活中发挥着不可替代的作用。基于有机电致发光二极管(OLED)的显示面板因其广色域、柔性、低能耗等技术优势，正在逐步替代液晶显示。适用于OLED器件的有机发光材料的不断发展是推动OLED技术不断进步的关键。
传统的有机发光材料主要为荧光和磷光材料。荧光材料由于三重态激子辐射跃迁禁阻，只能利用单重态激子发光，导致OLED器件的理论内量子效率上限只有25％，而外量子效率上限一般低于5％。含有铱、铂等贵金属的磷光材料通过重原子效应加强了单重态和三重态之间的自旋轨道耦合，使三重态激子可参与发光过程，因此磷光材料的器件理论内量子效率上限可提高到100％，外量子效率上限可提高到25～30％。2012年，九州大学Adachi教授证明了可利用具有热活化延迟荧光(TADF)性质的有机材料提升OLED器件的效率，实现100％的器件内量子效率上限。TADF材料在提高器件效率的同时，避免了贵金属的使用，可有效降低器件制备成本，故而引起了科学家们的广泛关注。
目前，基于TADF材料的OLED器件的一个突出问题是器件往往在高亮度下效率衰减严重，即效率滚降严重。而导致这一问题的关键因素之一是发光材料前线分子轨道之间的相互作用。研究发现，在给受体型TADF分子中引入大位阻的刚性螺环结构可阻断共轭面的延展，起到抑制临近分子间前线轨道相互作用的功效，进而减弱OLED器件的效率滚降。目前，文献中(Angew.Chem.Int.Ed.2019,58,11301–11305)主要是在给体单元中引入螺环结构，而在受体单元中引入螺环结构的示例较为少见。另外，含有B←N配位键的基团是一类应用广泛的电子受体基团，硼原子空的p轨道与N原子的配位不仅使得受体基团具有较强的受电子能力，同时可提升受体基团的结构刚性，有助于提升材料发光性能。将B←N配位键与螺环结构结合起来，设计新型的含硼受体单元，为解决OLED器件的效率滚降等问题提供了新的可行性方案。
发明内容
针对现有的技术问题，本发明提供了一种含硼氮配位键的螺结构化合物，并验证了它们在电致发光器件中的应用潜力。以其作为发光层或发光层掺杂材料的OLED器件不仅具有高亮度、高效率的优点，而且具有很低的效率滚降，有望满足面板制造企业的需求。
本发明所述的一种含硼氮配位键的螺结构化合物，其结构通式如(1)或(2)所示：
Figure BDA0003348471610000021
R1为取代或未取代的C6-C60的有机胺基团，可以与C1、C2、C3、C4中的1、2、3或4个碳原子相连，对应m的取值为1、2、3或4；
进一步的，R1为如下基团中的一种(R1通过波浪线的位置与C原子相连接)：
Figure BDA0003348471610000022
G为单键、取代(取代基团为烷基、芳基或杂芳基)或者未取代的C6～C48的芳基、取代(取代基团为烷基、芳基或杂芳基)或者未取代的C3～C48的杂芳基，所述杂原子为N、O、S、Si中的一种或多种。
R2选自氢、C1～C20的直链或者支链烷基、含有1～3个杂原子的C1～C20的杂烷基(所述的杂原子为N、O、S、Si中的一种或多种)、取代(取代基团为烷基或杂烷基)或未取代的C6～C48的芳基、取代(取代基团为烷基或杂烷基)或未取代的含有1～3个杂原子的杂芳基(所述杂原子为N、O、S、Si中的一种或多种)；n取值为0、1、2或3。
X为单键、O、S、Si、单芳基取代的氮原子、二烷基取代的碳原子、二芳基取代的碳原子或者通式(3)所示结构中的一种(波浪线的位置与C原子相连接)：
Figure BDA0003348471610000031
其中Y为单键、O、S、Si、单芳基取代的氮原子、二烷基取代的碳原子、二芳基取代的碳原子或者通式(4)所示结构中的一种(波浪线的位置与C原子相连接)：
Figure BDA0003348471610000032
进一步，本发明所述的一种含硼氮配位键的螺结构化合物，其结构如下之一所示：
Figure BDA0003348471610000041
Figure BDA0003348471610000051
Figure BDA0003348471610000061
本发明中，“取代”的位置如未做特别说明，位置可为任意。
“杂芳基”是指芳基中的一个或多个芳核碳被杂原子替换得到的基团的总称，所述杂原子包括氧、硫、氮或硅原子，所述杂芳基可以为单环杂芳基、多环杂芳基或稠环杂芳基，例如“C3～C48的杂芳基”包括但不限于吡啶基、喹啉基、咔唑基、噻吩基、苯并噻吩基、呋喃基、苯并呋喃基、嘧啶基、苯并嘧啶基、咪唑基或苯并咪唑基等。
本发明还提供了上述含硼氮配位键的螺结构有机电致发光材料的制备方法，可用路线(1)表示，
Figure BDA0003348471610000071
其中R1基团及数量m与前机所述含义相一致。Q可以为Br、I等卤素原子。
步骤1：将原料2、K2CO3、Pd(PPh3)4加入反应瓶中，抽换氮气后，先后加入原料1以及THF和水的混合溶剂，70℃加热反应12h，除去溶剂后柱层析法得到无色油状中间体1。
步骤2：将中间体1溶解在二氯甲烷中，冰浴条件下加入DIEA，搅拌后加入BBr3室温搅拌，快速冲硅胶得到白色中间体2。
步骤3：将中间体2和原料3溶于二氯甲烷中，加入无水AlCl3常温搅拌，处理得到中间体3。
步骤4：①当G为单键时，即原料4为R1-H时，用甲苯溶解中间体3和原料4，加入t-BuONa、Pd2(dba)3和Sphos，升温至回流，反应12h；将反应液倒入水中，二氯甲烷萃取三次，合并有机层，旋干；再经硅胶柱层析得通式(1)中的化合物。
②当G为芳基或者杂芳基时，即原料4为R1-B(OH)2时，用四氢呋喃和水的混合溶剂溶解原料4和中间体3，而后加入K2CO3和Pd(PPh3)4，升温至回流，反应12h；将反应液倒入水中，二氯甲烷萃取三次，合并有机层，旋干；再经硅胶柱层析得通式(1)中的化合物。
步骤5：将原料1替换成原料5，其他操作程序与步骤1一致。
步骤6：将中间体1替换成中间体4，其他操作程序与步骤2一致。
步骤7：将中间体2替换成中间体5，其他操作程序与步骤3一致。
步骤8：与步骤4一致，唯一的区别是使用中间体6作为原料，可得通式(2)中的化合物。
原料2包括但不限于以下结构化合物：
Figure BDA0003348471610000081
原料4包括但不限于以下结构化合物：
Figure BDA0003348471610000082
与现有技术相比，本发明的优点在于：
本发明所述的含硼氮配位键的螺结构化合物不仅可以用作发光层掺杂材料、还可以直接用作发光层，并且都获得了优异的器件性能。与对比器件相比，器件的最大亮度、外量子效率、电流效率和功率效率，均有非常大的改善。而且，聚集猝灭和效率滚降得到了有效的控制。综上所述，鉴于本发明所述化合物在OLEDs中的优异性能，所述化合物在OLEDs领域中的应用潜力将会非常巨大。
具体实施方式
实施例1：化合物1的合成
Figure BDA0003348471610000091
(1)在干燥的250mL双口瓶中加入b(10mmol)、K2CO3(25mmol)、Pd(PPh3)4(0.25mmol)后，置换氮气三次。加入鼓泡20min的THF和水的混合溶剂后(体积比，THF：H2O＝2:1)，加入a(10mmol)，加热回流12h。用二氯甲烷萃取后，合并有机相，旋干溶剂。柱层析法得到化合物c。
(2)在干燥的双口瓶中加入c(20mmol)，置换氮气后加入无水无氧的二氯甲烷溶解，冰浴条件下加入DIEA(4mL)，搅拌20min。继续加入BBr3(60mL)后升至室温搅拌6h。反应结束后减压抽走溶剂和过量的BBr3。用K2CO3溶液淬灭，二氯甲烷萃取后旋干有机相。用三氧化铝柱层析法提纯得到化合物d。
(3)在干燥的双口瓶中加入d(10mmol)、e(10mmol)、AlCl3(1mmol)抽换氮气后冰浴条件下加入50mL无水无氧的二氯甲烷，室温搅拌过夜。旋干溶剂后通过柱层析法得到化合物f。
(4)在干燥的250mL双口瓶中加入f(2mmol)、g(2.5mmol)、Pd2(dpa)3(0.02mmol)、Sphos(0.04mmol)、叔丁醇钠(5mmol)后置换氮气三次，加入干燥的甲苯60mL,加热回流18h。将混合液萃取后旋干有机相，柱层析法得到化合物1.产率：60％。HRMS：理论值：648.2737，实验值：648.2736。
实施例2：化合物2的合成
Figure BDA0003348471610000101
按照上述反应路线，依照化合物1的合成，步骤相同，合成得到化合物2。产率为58％。HRMS：理论值：647.2533，实验值：647.2530。
实施例3：化合物3的合成
Figure BDA0003348471610000102
按照上述反应路线，依照化合物1的合成，步骤相同，合成得到化合物3。产率为61％。HRMS：理论值：702.3206，实验值：702.3205。
实施例4：化合物11的合成
Figure BDA0003348471610000103
按照上述反应路线，依照化合物1的合成，步骤相同，合成得到化合物11，产率为62％。HRMS：理论值：811.3159，实验值：811.3152。
实施例5：化合物12的合成
Figure BDA0003348471610000111
按照上述反应路线，依照化合物1的合成，步骤相同，合成得到化合物12，产率为64％。HRMS：理论值：826.2975，实验值：826.2977。
实施例6：化合物17的合成
Figure BDA0003348471610000112
按照上述反应路线，依照化合物1的合成，步骤相同，合成得到化合物17，产率为61％。HRMS：理论值：827.3108，实验值：827.3106。
实施例7：化合物18的合成
Figure BDA0003348471610000113
按照上述反应路线，依照化合物1的合成，步骤相同，合成得到化合物18，产率为80％。HRMS：理论值：738.2842，实验值：738.2841。
实施例8：化合物19的合成
Figure BDA0003348471610000121
按照上述反应路线，依照化合物1的合成，步骤相同，合成得到化合物19，合成产率为75％。HRMS：理论值：995.3683，实验值：995.3680。
实施例9：化合物21的合成
Figure BDA0003348471610000122
按照上述反应路线，依照化合物1的合成，步骤相同，合成得到化合物21，产率为52％。HRMS：理论值：902.3217，实验值：902.3215。
实施例10：化合物22的合成
Figure BDA0003348471610000123
按照上述反应路线，依照化合物1的合成，步骤相同，合成得到化合物22，产率为59％。HRMS：理论值：646.600，实验值：646.5988。
实施例11：化合物29的合成
Figure BDA0003348471610000131
按照上述反应路线，依照化合物1的合成，步骤相同，合成得到化合物29，产率为66％。HRMS：理论值：815.3472，实验值：815.3470。
实施例12：化合物35的合成
Figure BDA0003348471610000132
按照上述反应路线，依照化合物1的合成，步骤相同，合成得到化合物35，产率为62％。HRMS：理论值：811.3159，实验值：811.3156。
实施例13：化合物40的合成
Figure BDA0003348471610000141
按照上述反应路线，依照化合物1的合成，步骤相同，合成得到化合物40，产率为67％。HRMS：理论值：975.3785，实验值：975.3783。
实施例14：化合物53的合成
Figure BDA0003348471610000142
按照上述反应路线，依照化合物1的合成，步骤相同，合成得到化合物53，产率为49％。HRMS：理论值：765.3315，实验值：765.3313。
实施例15：化合物54的合成
Figure BDA0003348471610000143
按照上述反应路线，依照化合物1的合成，步骤相同，合成得到化合物54，产率为49％。HRMS：理论值：764.7790，实验值：764.7789。
实施例16：化合物58的合成
Figure BDA0003348471610000151
按照上述反应路线，依照化合物1的合成，步骤相同，合成得到化合物58，产率为58％。HRMS：理论值：741.6610，实验值：741.6609。
实施例17：化合物59的合成
Figure BDA0003348471610000152
按照上述反应路线，依照化合物1的合成，步骤相同，合成得到化合物59，产率为59％。HRMS：理论值：741.2700，实验值：741.2698。
实施例18：化合物60的合成
Figure BDA0003348471610000153
按照上述反应路线，依照化合物1的合成，步骤相同，合成得到化合物60，产率为61％。HRMS：理论值：795.2516，实验值：795.2514。
实施例19：化合物62的合成
Figure BDA0003348471610000161
按照上述反应路线，依照化合物1的合成，步骤相同，合成得到化合物62，产率为68％。HRMS：理论值：887.8930，实验值：887.8929。
实施例20：化合物63的合成
Figure BDA0003348471610000162
按照上述反应路线，依照化合物1的合成，步骤相同，合成得到化合物63，合成产率为55％。HRMS：理论值：945.3890，实验值：945.3889。
实施例21：
本发明还提供了一种有机电致发光器件，包括具有阴极和阳极组成的一对电极对，在这一对电极对中间，至少包含一层发光层，本发明所述的含硼氮配位键的螺结构化合物单独作为发光层使用，或作为掺杂材料与主体材料共同作为发光层使用。
所述的有机电致发光器件中包括玻璃基板、阳极材料(Anode)、空穴注入层(HIL)、空穴传输层(HTL)、电子阻挡层(EBL)、发光层(EML)、空穴阻挡层(HBL)电子传输层(ETL)、电子注入层(EIL)和阴极材料(Cathode)。从玻璃基板开始，依次往上生长，其中，发光层位于电子阻挡层和空穴阻挡层之间，且发光层中包含有本发明所述的任一种含硼氮配位键的螺结构化合物。
所述器件选用的阳极材料为ITO，空穴注入层为HATCN，厚度为10nm；空穴传输层为α-NPD，厚度为40nm；电子阻挡层为CCP，厚度为5nm；当本发明所述含硼氮配位键的螺结构化合物作为发光掺杂材料时，选用PPF作为主体材料，厚度为20nm，其中掺杂浓度为20％；空穴阻挡层为PPF，厚度为10nm；电子传输层为TPBi，厚度为30nm；电子注入层为LiF，厚度为1nm；阴极材料为铝，厚度为100nm。相关化合物的结构式如下所示：
Figure BDA0003348471610000171
本发明的化合物可以作为发光层掺杂材料使用，对本发明化合物1、2、3、11、12、17、18、19、21、22、29、35、40、53、54、58、59、60、62、63和经典材料4CZIPN分别进行电致发光器件性能表征。使用的器件结构为ITO/HATCN(10nm)/α-NPD(40nm)/CCP(5nm)/PPF：x(20wt％，20nm)/PPF(10nm)/TPBi(30nm)/LiF(1nm)/Al(100nm)，x代表本发明所制备的化合物。
器件制备过程：将透明阳极电极ITO基板在异丙醇中超声清洗15分钟，并暴露在紫外光下30分钟，随后用plasma处理10分钟。随后将处理后的ITO基板放入蒸镀设备。依次蒸镀HATCN、α-NPD、CCP、发光层、PPF、TPBi，蒸镀速率为0.1nm/s。在电子传输层TPBi上依次真空蒸镀LiF和Al作为阴极，蒸镀速率为1nm/s。
上述方法制备的电致发光器件的器件性能如表1所示：
表1.所述的含硼氮配位键的螺结构化合物作为发光层掺杂材料的器件性能汇总
Figure BDA0003348471610000181
Figure BDA0003348471610000191
注：滚降表示的是当亮度升高到1000cd m-2时的EQE下降幅度。
从表1中数据可知，本发明所述的含硼氮配位键的螺结构化合物作为发光层掺杂材料应用在有机电致发光器件中，在高掺杂浓度下具有低开启电压、高亮度、高效率、低滚降的优点。与使用材料4CZIPN制成的电致发光器件相比，发光亮度和效率均有明显的提高，而且效率滚降得到了显著的控制。
本发明的化合物可以直接作为发光层使用，对本发明化合物1、2、3、11、12、17、18、19、21、22、29、35、40、53、54、58、59、60、62、63和经典材料4CZIPN分别进行非掺杂电致发光器件性能表征。使用的器件结构为ITO/HATCN(10nm)/α-NPD(40nm)/CCP(5nm)/EML(20nm)/PPF(20nm)/TPBi(30nm)/LiF(1nm)/Al(100nm)。EML表示发光层，为本发明所述的化合物中的一种。
器件制备过程：将透明阳极电极ITO基板在异丙醇中超声清洗15分钟，并暴露在紫外光下30分钟，随后用plasma处理10分钟。随后将处理后的ITO基板放入蒸镀设备。依次蒸镀HATCN、α-NPD、CCP、发光层、TPBi，蒸镀速率为0.1nm/s。在电子传输层TPBi上依次真空蒸镀LiF和Al作为阴极，蒸镀速率为1nm/s。
上述方法制备的电致发光器件的器件性能如表2所示：
表2.所述的含硼氮配位键的螺结构化合物作为发光层的器件性能汇总
Figure BDA0003348471610000192
Figure BDA0003348471610000201
注：滚降表示的是当亮度升高到1000cd m-2时的EQE下降幅度。
从表2中数据可知，本发明所述的含硼氮配位键的螺结构化合物作为发光层应用在有机电致发光器件中，依然具有低开启电压、高亮度、高效率、低滚降的优点。与经典材料4CZIPN相比，器件性能明显改善。
综合表1、表2的数据可以明显的看到，本发明中的含硼氮配位键的螺结构化合物无论是用做掺杂器件还是非掺杂器件，都是一种性能优良的有机电致发光材料。
虽然已通过实施例和优选实例的方式公开了本发明，但应理解，本发明不限于所公开的实施方式。相反，本领域技术人员应该明白，其意在涵盖各种变型，在不脱离本发明的原理的前提下，还可以对本发明进行若干修饰和改进。因此，所附权利要求的范围应与最宽的理解相一致以涵盖所有这样的变型和修饰。

Claims (4)

1.一种含硼氮配位键的螺结构化合物，其特征在于：其结构通式如(1)或(2)所示，
Figure FDA0003348471600000011
R1为取代或未取代的C6-C60的有机胺基团，与C1、C2、C3、C4中的1、2、3或4个碳原子相连，对应m的取值为1、2、3或4。
2.如权利要求1所述的一种含硼氮配位键的螺结构化合物，其特征在于：R1为如下基团中的一种，
Figure FDA0003348471600000012
G为单键、取代(取代基团为烷基、芳基、杂芳基)或者未取代的C6～C48的芳基、取代(取代基团为烷基、芳基、杂芳基)或者未取代的C3～C48的杂芳基，所述杂原子为N、O、S、Si中的一种或多种；
R2选自氢、C1～C20的直链或者支链烷基、含有1～3个杂原子的C1～C20的杂烷基、取代(取代基团为烷基或杂烷基)或未取代的C6～C48的芳基、取代(取代基团为烷基或杂烷基)或未取代的含有1～3个杂原子的杂芳基；杂原子为N、O、S、Si中的一种或多种；
n取值为0、1、2或3；
X为单键、O、S、Si、单芳基取代的氮原子、二烷基取代的碳原子、二芳基取代的碳原子或者通式(3)所示结构中的一种，
Figure FDA0003348471600000021
其中Y为单键、O、S、单芳基取代的氮原子、二烷基取代的碳原子、二芳基取代的碳原子或者通式(4)所示结构中的一种，
Figure FDA0003348471600000022
3.如权利要求1所述的一种含硼氮配位键的螺结构化合物，其特征在于：其结构式如下之一所示，
Figure FDA0003348471600000031
Figure FDA0003348471600000041
Figure FDA0003348471600000051
Figure FDA0003348471600000061
4.一种有机电致发光器件，包括具有阴极和阳极组成的一对电极对，在这一对电极对中间，至少包含一层发光层，其特征在于：权利要求1～3任意一项所述的含硼氮配位键的螺结构化合物单独作为发光层使用，或作为掺杂材料与主体材料共同作为发光层使用。
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