CN110183302B - 一种稠合三联苯化合物及其制备方法和用途 - Google Patents

一种稠合三联苯化合物及其制备方法和用途 Download PDF

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CN110183302B
CN110183302B CN201910463426.3A CN201910463426A CN110183302B CN 110183302 B CN110183302 B CN 110183302B CN 201910463426 A CN201910463426 A CN 201910463426A CN 110183302 B CN110183302 B CN 110183302B
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terphenyl
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CN110183302A (zh
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魏定纬
张晓晓
丁欢达
陈志宽
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Ningbo Jizhi Innovation Material Research Institute Co ltd
Ningbo Lumilan Advanced Materials Co Ltd
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Ningbo Lumilan Advanced Materials Co Ltd
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Abstract

本发明公开了一种稠合三联苯化合物及其制备方法和用途。所述的稠合三联苯化合物具有如式(I)所示的结构。稠合三联苯化合物的母核为稠合三联苯，由于三个苯环非共平面，有利于提高分子的热稳定性，此外，稠合三联苯的非平面结构还能够避免分子堆叠，有助于激子生成，提高材料的发光效率。通过设置R1、R2取代基，使式(I)所示的化合物整体结构刚性高，可提高分子的热稳定性，增加材料的使用寿命。本发明还公开了一种有机电致发光器件，至少有一个功能层中含有上述的稠合三联苯化合物，稠合三联苯化合物作为发光层的主体材料或客体材料，稳定性高，器件发光效率高。

Description

一种稠合三联苯化合物及其制备方法和用途
技术领域
本发明涉及显示技术领域，具体涉及一种稠合三联苯化合物及其制备方法和用途。
背景技术
有机电致发光器件(organic light-emitting diodes，OLED)由于具有驱动电压低、发光效率高、对比度高、色饱和度高、能耗低、主动发光、视角宽、响应快等优点，在显示和照明领域有极大的应用前景，越来越受到人们的重视。
1987年，美国Kodak公司的Tang等利用真空沉积镀膜的方法制备出多层结构的OLED器件。OLED器件以导电的氧化铟锡(ITO)作为阴极，并在上面依序蒸镀芳香胺衍生物与三(8-羟基喹啉)铝，阳极材料则使用镁银合金，得到了具有高亮度(1000cd/m2)的绿光发光器件。同时，由于对器件结构进行优化，增加了以芳香胺衍生物形成的空穴传输层，实现了较高的发光亮度和发光效率，并使驱动电压降低到10V以下。此后，有机电致发光材料的研究引起了广泛关注。
荧光材料是最早应用的第一代OLED材料，但是此类材料所组成的器件效率低，仅仅能利用材料25％的单线态激子发光，75％的三线态电致激子由于自旋禁阻作用以非辐射失活的形式回到基态，很大程度上限制了器件的效率。直到1998年，Baldo等首次报道通过在有机小分子中引入铱(III)、铂(II)以及锇(II)等金属形成配合物，可以通过自旋耦合作用使得材料的三线态激子能够辐射跃迁发出磷光，获得了理论上100％的内量子效率。2012年日本九州大学Chihaya Adachi教授发现了具有小的单线态-三线态能级差(ΔEST)的TADF材料，TADF材料的三线态激子可以通过反系间窜越(RISC)转变成单线态激子发光，充分利用了之前无法利用的75％的三线态激子，器件的内量子效率可以达到100％。
目前，磷光材料和TADF材料的开发使得红色、绿色的发光材料已经能够满足有机电致发光器件的发光性能要求。然而，蓝光发光材料由于吸收光谱的波长较短、LUMO与HOMO间的带隙宽，使得蓝光发光材料的辐射发光需要获得更多能量，限制了蓝光器件的发光效率。具有高发光效率的蓝光材料的种类少，且发光颜色偏蓝绿色的发光区域，难以实现深蓝色发光。蓝光发光材料主要是共轭片段简单的平面芳香环分子，热稳定性低，在成膜和使用过程中容易因热量而发生分解，影响器件的效率和寿命；同时，平面型的芳香环分子发生相互堆叠，容易形成激基双体，激子的能量增高产生湮灭，使器件的发光效率降低，使用寿命缩短，发光颜色也会发生改变、产生色偏，以上均制约了蓝光有机电致发光器件的应用与发展。
发明内容
因此，本发明要解决的技术问题在于克服现有技术中的蓝光发光材料热稳定性低、激子易发生湮灭，使器件的发光效率降低、使用寿命缩短的缺陷，从而提供一种稠合三联苯化合物及其制备方法和用途。
第一方面，本发明提供了一种稠合三联苯化合物，具有式(I)所示的结构：
Figure BDA0002078734320000031
其中，R1-R10彼此独立地选自氢、氘、卤素、烷基、烯基、炔基、环烷基、环烯基、环炔基、烷胺基、烯胺基、炔胺基、烷氧基、烯氧基、炔氧基、硫代烷氧基、硫代烯氧基、硫代炔氧基、烷硼基、烯硼基、炔硼基、酯基、酰胺基、芳基、杂芳基、芳胺基、芳氧基、硫代芳氧基或芳硼基；
Ar1、Ar2彼此独立地选自芳基或杂芳基。
进一步地，上述的稠合三联苯化合物，R1-R10彼此独立地选自氢、氘、卤素、C1-C60的取代或未取代的烷基、C1-C60的取代或未取代的烯基、C1-C60的取代或未取代的炔基、C3-C60的取代或未取代的环烷基、C4-C60的取代或未取代的环烯基、C5-C60的取代或未取代的环炔基、C1-C60的取代或未取代的烷胺基、C1-C60的取代或未取代的烯胺基、C1-C60的取代或未取代的炔胺基、C1-C60的取代或未取代的烷氧基、C1-C60的取代或未取代的烯氧基、C1-C60的取代或未取代的炔氧基、C1-C60的取代或未取代的硫代烷氧基、C1-C60的取代或未取代的硫代烯氧基、C1-C60的取代或未取代的硫代炔氧基、C1-C60的取代或未取代的烷硼基、C1-C60的取代或未取代的烯硼基、C1-C60的取代或未取代的炔硼基、C1-C60的取代或未取代的酯基、C1-C60的取代或未取代的酰胺基、C4-C60的取代或未取代的芳基、C3-C60的取代或未取代的杂芳基、C4-C60的取代或未取代的芳胺基、C4-C60的取代或未取代的芳氧基、C4-C60的取代或未取代的硫代芳氧基、C4-C60的取代或未取代的芳硼基；Ar1、Ar2彼此独立地选自C4-C60的取代或未取代的芳基、C3-C60的取代或未取代的杂芳基。
进一步地，上述的稠合三联苯化合物，R3-R6中的任意相邻的两个或多个基团连接形成C4-C60的取代或未取代的芳基、C3-C60的取代或未取代的杂芳基、C2-C60的取代或未取代的稠环。
进一步地，上述的稠合三联苯化合物，R7-R10中的任意相邻的两个或多个基团连接形成C4-C60的取代或未取代的芳基、C3-C60的取代或未取代的杂芳基、C2-C60的取代或未取代的稠环。
进一步地，上述的稠合三联苯化合物，具有如下任一所示的分子结构：
Figure BDA0002078734320000041
Figure BDA0002078734320000051
Figure BDA0002078734320000061
Figure BDA0002078734320000071
Figure BDA0002078734320000081
Figure BDA0002078734320000091
Figure BDA0002078734320000101
Figure BDA0002078734320000111
Figure BDA0002078734320000121
Figure BDA0002078734320000131
Figure BDA0002078734320000141
Figure BDA0002078734320000151
Figure BDA0002078734320000161
Figure BDA0002078734320000171
Figure BDA0002078734320000181
Figure BDA0002078734320000191
Figure BDA0002078734320000201
Figure BDA0002078734320000211
Figure BDA0002078734320000221
Figure BDA0002078734320000231
Figure BDA0002078734320000241
Figure BDA0002078734320000251
Figure BDA0002078734320000261
Figure BDA0002078734320000271
Figure BDA0002078734320000281
Figure BDA0002078734320000291
Figure BDA0002078734320000301
Figure BDA0002078734320000311
Figure BDA0002078734320000321
Figure BDA0002078734320000331
Figure BDA0002078734320000341
Figure BDA0002078734320000351
Figure BDA0002078734320000361
Figure BDA0002078734320000371
Figure BDA0002078734320000381
Figure BDA0002078734320000391
Figure BDA0002078734320000401
Figure BDA0002078734320000411
Figure BDA0002078734320000421
第二方面，本发明提供了一种上述稠合三联苯化合物的制备方法，
所述式(I)所示化合物的合成步骤如下所示：以式(C)所示的化合物为起始原料，经偶联反应得到中间体2；中间体2经过脱水反应得到中间体3；中间体3经过加成反应和取代反应得到中间体4；中间体4经偶联反应，得到式(I)所示的化合物；
所述式(I)所示化合物的合成路线如下所示：
Figure BDA0002078734320000422
。
进一步地，所述式(C)所示化合物的合成步骤如下所示：以式(A)所示的化合物和碘为起始原料，经过卤代反应得到式(B)所示的化合物；式(B)所示的化合物经过氧化反应得到式(C)所示化合物；
所述式(C)所示化合物的合成路线如下所示：
Figure BDA0002078734320000431
进一步地，由式(C)所示的化合物得到中间体2的步骤如下所示：以式(C)所示的化合物和式(D)所示的化合物为原料，经过偶联反应得到中间体1；中间体1和式(E)所示的化合物经过偶联反应得到中间体2；
由式(C)所示的化合物得到中间体2的合成路线如下所示：
Figure BDA0002078734320000432
。
进一步地，由中间体4得到式(I)所示的化合物的步骤如下所示：以中间体4和式(F)或(G)所示的化合物为原料，经过偶联反应得到中间体5；中间体5和式(H)或(J)所示的化合物，经过偶联反应得到式(I)所示的化合物；
由中间体4得到式(I)所示的化合物的合成路线如下所示：
Figure BDA0002078734320000441
。
进一步地，本发明提供了一种上述稠合三联苯化合物作为有机电致发光材料的用途。
进一步地，本发明提供了一种有机电致发光器件，所述有机电致发光器件的至少一个功能层中含有上述的稠合三联苯化合物。
进一步地，上述有机电致发光器件，所述功能层为发光层。
进一步地，上述有机电致发光器件，所述发光层材料包括主体材料和客体材料，所述主体材料或所述客体材料为所述稠合三联苯化合物。
本发明技术方案，具有如下优点：
1.本发明提供的稠合三联苯化合物，具有如式(I)所示的结构，其母核为稠合三联苯，由于三个苯环非共平面，有利于提高分子的热稳定性，此外，稠合三联苯的非平面结构还能够避免分子堆叠，有助于激子生成，提高材料的发光效率。
通过设置R1、R2取代基，使式(I)所示的化合物整体结构刚性高，可提高分子的热稳定性，增加材料的使用寿命。
2.本发明提供的稠合三联苯化合物，通过调节R3-R10取代基，能够在苯环上引入吸电子基团或是供电子基团，HOMO能级分布于供电子基团，LUMO能级分布于吸电子基团，进一步提高材料分子的空穴传输性能和电子传输性能，提高其电荷传输的平衡性；在作为发光层主体材料时，防止三线态激子由于高浓度引发的浓度湮灭或者单线态-三线态激子湮灭。通过设置供电子基团和吸电子基团，稠合三联苯化合物的HOMO能级提高，LUMO能级降低，在作为发光层主体材料时，有利于进一步匹配相邻的空穴和电子型的载流子功能层。
如图1和图2所示，稠合三联苯化合物通过将HOMO和LUMO分布于不同的供电子基团和吸电子基团上，使HOMO能级和LUMO能级有效分离，减小了材料分子的单线态和三线态能级差△Est(≤0.3eV)，有利于三线态激子向单线态激子的反系间窜越，促进主体材料向客体材料的能量转移，减少能量传递过程中的损失。
3、本发明提供的稠合三联苯化合物的制备方法，起始原料易于获得，反应条件温和，操作步骤简单，为上述稠合三联苯化合物的大规模生产提供了一种简单、易于实现的制备方法。
4、本发明提供的有机电致发光(OLED)器件，至少有一个功能层中含有上述的稠合三联苯化合物，其中，所述功能层为发光层。
上述的稠合三联苯化合物，具有优良的热稳定性，还能够避免分子堆叠，有助于激子生成，提高材料的发光效率。
通过调节取代基团，进一步提高稠合三联苯化合物的电子、空穴的传输性能，发光层中电荷和空穴的传输更加平衡，从而扩大了发光层中空穴和电子复合为电子的区域，降低激子浓度，防止器件的三线态-三线态湮灭，提高器件效率；并且能使载流子复合的区域远离发光层与空穴或者电子传输层的相邻界面，提高OLED器件的色纯度，避免激子向传输层的回传，进一步提高器件效率。
上述的稠合三联苯化合物利用供电子基团和吸电子基团调节材料分子的HOMO能级和LUMO能级，减小HOMO能级与LUMO能级的交叠，使化合物具有小的△Est，促进了三线态激子向单线态激子转化的反系间穿越(RISC)，从而抑制从主体材料到发光染料的德克斯特能量转移(DET)，促进能量转移，减少德克斯特能量转移(DET)过程中的能量损失，有效降低了有机电致发光器件的效率滚降，器件的外量子效率提高。
附图说明
为了更清楚地说明本发明具体实施方式或现有技术中的技术方案，下面将对具体实施方式或现有技术描述中所需要使用的附图作简单地介绍，显而易见地，下面描述中的附图是本发明的一些实施方式，对于本领域普通技术人员来讲，在不付出创造性劳动的前提下，还可以根据这些附图获得其他的附图。
图1是式(Ia)所示的化合物的HOMO能级、LOMO能级和ΔEst的理论计算结果图；
图2是式(Ib)所示的化合物的HOMO能级、LOMO能级和ΔEst的理论计算结果图；
图3是本发明实施例10-18和对比例1中有机电致发光器件的结构示意图；
附图标记说明：
1-阳极，2-空穴注入层，3-空穴传输层，4-发光层，5-电子传输层，6-电子注入层，7-阴极。
具体实施方式
下面将结合附图对本发明的技术方案进行清楚、完整地描述，显然，所描述的实施例是本发明一部分实施例，而不是全部的实施例。基于本发明中的实施例，本领域普通技术人员在没有做出创造性劳动前提下所获得的所有其他实施例，都属于本发明保护的范围。
在本发明的描述中，需要说明的是，术语“第一”、“第二”、“第三”仅用于描述目的，而不能理解为指示或暗示相对重要性。
本发明可以以许多不同的形式实施，而不应该被理解为限于在此阐述的实施例。相反，提供这些实施例，使得本公开将是彻底和完整的，并且将把本发明的构思充分传达给本领域技术人员，本发明将仅由权利要求来限定。在附图中，为了清晰起见，会夸大层和区域的尺寸和相对尺寸。应当理解的是，当元件例如层被称作“形成在”或“设置在”另一元件“上”时，该元件可以直接设置在所述另一元件上，或者也可以存在中间元件。相反，当元件被称作“直接形成在”或“直接设置在”另一元件上时，不存在中间元件。
本申请提供一种稠合三联苯化合物，合成步骤如下所示：以式(A)所示的化合物和碘为起始原料，经过卤代反应得到式(B)所示的化合物；式(B)所示的化合物经过氧化反应得到式(C)所示化合物；式(C)所示的化合物和式(D)所示的化合物经过偶联反应得到中间体1；中间体1和式(E)所示的化合物经过偶联反应得到中间体2；中间体2经过脱水反应得到中间体3；中间体3经过加成反应和取代反应得到中间体4；中间体4和式(F)或(G)所示的化合物经过偶联反应得到中间体5；中间体5和式(H)或(J)所示的化合物经过偶联反应得到式(I)所示的化合物。
所述式(I)所示化合物的合成路线如下所示：
Figure BDA0002078734320000491
实施例1
本实施例提供一种稠合三联苯化合物，具有下述式(P-009)所示的结构：
Figure BDA0002078734320000501
式(P-009)所示稠合三联苯化合物的合成路径如下所示：
Figure BDA0002078734320000502
其中，式(C)所示的化合物的合成路径如下所示：
Figure BDA0002078734320000503
式(P-009)所示稠合三联苯化合物的具体包括以下步骤：
(1)合成化合物C
取2升双颈圆底瓶并放入搅拌子与上接回流管，干燥后充入氮气，分别加入263.96克化合物A(1.0当量)、892.02克K2S2O8(3.3当量)及837.57克碘(3.3当量)，加入1000毫升二氯甲烷并降温至0℃，搅拌混合10分钟，缓慢滴加375毫升TFA和17毫升硫酸的混合溶液，以铝箔包覆双颈圆底瓶后加热至60℃，反应24小时，待其回温后用1250毫升冰水淬灭反应，用二氯甲烷萃取，每次500毫升，萃取三次，所得到的萃取液依序加入硫酸镁干燥、过滤及旋干，粗产物以丙酮清洗，每次200毫升，清洗三次后得到化合物B(273.35克，产率53％)；
取5升双颈圆底瓶并放入搅拌子与上接回流管，干燥后充入氮气，分别加入257.88克化合物B(1.0当量)和79.016克高锰酸钾(10.0当量)，加入1200毫升吡啶和160毫升水的混合溶液并搅拌混合10分钟，加热回流并每小时追加高锰酸钾共四次，每次加79.016克高锰酸钾(10.0当量)，反应18小时，待其回温后过滤，接着用85℃的10％氢氧化钾水溶液清洗所得到的固体，每次750毫升，清洗三次，收集所得洗液并浓缩至1000毫升，待其回温后过滤，以浓盐酸酸化，接着降温至0℃过滤，最后用水清洗所得到的固体，每次50毫升，清洗三次，并在70℃下干燥过夜，粗产物以乙醇再结晶后得到化合物C(207.26克，产率72％)；
元素分析：(C8H2Br2I2O4)理论值：C,16.69；H,0.35；实测值：C,16.66；H,0.37；HRMS(ESI)m/z(M+)：理论值575.6389；实测值：575.6380；
(2)合成中间体2-1
取100毫升双颈圆底瓶并内置搅拌子与上接回流管，干燥后充入氮气，分别加入5.757克的化合物C(1.0当量)、2.804克苯硼酸(2.3当量)、0.578克Pd(PPh3)4(5mol％)及2.649克碳酸钠(2.5当量)，加入40毫升甲苯和和4毫升水，并搅拌混合10分钟，加热回流并反应18小时，待其回温后加入30毫升水，接着用乙酸乙酯萃取，每次20毫升，萃取三次，所得到的萃取液依序加入硫酸镁干燥、过滤及旋干，粗产物以层析纯化(乙酸乙酯/己烷，1/20)，得到中间体2-1(3.476克，产率73％)；
(3)合成中间体3-1
取50毫升双颈圆底瓶并内置搅拌子与上接回流管，干燥后充入氮气，加入3.333克中间体2-1(1.0当量)，加入2毫升盐酸和20毫升醋酸，搅拌混合10分钟，加热回流并反应6小时，待其回温后加入10毫升水，用乙酸乙酯萃取，每次20毫升，萃取三次，所得到的萃取液依序加入硫酸镁干燥、过滤及旋干，粗产物以层析纯化(乙酸乙酯/己烷，1/15)，得到中间体3-1(3.050克，产率99％)；
(4)合成中间体4-1
取100毫升双颈圆底瓶并内置搅拌子与上接回流管，干燥后充入氮气，分别加入2.200克中间体3-1(1.0当量)与0.018克苯甲酸(3mol％)，加入15毫升二甲苯并搅拌混合10分钟，加入三甲基铝(2.0mol/L)与12毫升甲苯溶液(4.8当量)，加热至回流并反应48小时，待其回温后用20毫升HCl(0.5mol/L)与20毫升乙醚的混合溶液水解，用二氯甲烷萃取，每次50毫升，萃取三次，所得到的萃取液依序加入硫酸镁干燥、过滤及旋干，粗产物以层析纯化(乙酸乙酯/己烷，1/25)，得到化合物中间体4-1(1.007克，产率43％)；
(5)合成化合物P-009
取25毫升双颈圆底瓶并内置搅拌子与上接回流管，干燥后充入氮气，分别加入0.936克中间体4-1(1.0当量)、0.244克苯硼酸(1.0当量)、0.116克Pd(PPh3)4(5mol％)及0.530克碳酸钠(2.5当量)，接着加入10毫升甲苯和1毫升水，搅拌混合10分钟，加热回流并反应12小时，待其回温后加入0.645克化合物H-1(1.3当量)，重新加热至回流并反应12小时，待其回温后加入10毫升水，接着用乙酸乙酯萃取，每次20毫升，萃取三次，所得到的萃取液依序加入硫酸镁干燥、过滤及旋干，粗产物以层析纯化(乙酸乙酯/己烷，1/25)，得到化合物P-009(1.024克，产率87％)。
元素分析：(C46H36)理论值：C,93.84；H,6.16；实测值：C,93.80；H,6.18；HRMS(ESI)m/z(M+)：理论值：588.2817；实测值：588.2819。
实施例2
本实施例提供一种稠合三联苯化合物，具有下述式(P-040)所示的结构：
Figure BDA0002078734320000531
式(P-040)所示稠合三联苯化合物的合成路径如下所示：
Figure BDA0002078734320000532
式(P-040)所示稠合三联苯化合物的制备方法具体包括以下步骤：
以式(C)所示的化合物和苯硼酸为原料，依据实施例1中提供的合成方法，其不同之处在于，在步骤(5)中用化合物H-2替代化合物H-1，得到式(P-040)所示的稠合三联苯化合物(1.065克，产率92％)。
元素分析：(C45H38)理论值：C,93.38；H,6.62；实测值：C,93.41；H,6.59；HRMS(ESI)m/z(M+)：理论值：578.2974；实测值：578.2889。
实施例3
本实施例提供一种稠合三联苯化合物，具有下述式(P-041)所示的结构：
Figure BDA0002078734320000541
式(P-041)所示稠合三联苯化合物的合成路径如下所示：
Figure BDA0002078734320000542
式(P-041)所示稠合三联苯化合物的制备方法具体包括以下步骤：
以式(C)所示的化合物和苯硼酸为原料，依据实施例1中提供的合成方法，其不同之处在于，在步骤(5)中用化合物H-3替代化合物H-1，得到式(P-041)所示的稠合三联苯化合物(1.050克，产率95％)。
元素分析：(C42H32O)理论值：C,91.27；H,5.84；实测值：C,91.23；H,5.86；HRMS(ESI)m/z(M+)：理论值：552.2453；实测值：552.2457。
实施例4
本实施例提供一种稠合三联苯化合物，具有下述式(P-078)所示的结构：
Figure BDA0002078734320000551
式(P-078)所示稠合三联苯化合物的合成路径如下所示：
Figure BDA0002078734320000552
式(P-078)所示稠合三联苯化合物的制备方法具体包括以下步骤：
步骤(1)-(4)同实施例1；
(5)合成中间体5-4
取25毫升双颈圆底瓶并内置搅拌子与上接回流管，干燥后充入氮气，分别加入0.936克中间体4-4(1.0当量)、0.268克苯硼酸(1.1当量)、0.116克Pd(PPh3)4(5mol％)及0.530克碳酸钠(2.5当量)，接着加入甲苯(10毫升)和水(1毫升)，并搅拌混合10分钟，加热回流并反应12小时，待其回温后加入10毫升水，接着用乙酸乙酯萃取，每次20毫升，萃取三次，所得到的萃取液依序加入硫酸镁干燥、过滤及旋干，粗产物以层析纯化(乙酸乙酯/己烷，1/20)，得到中间体5-4(0.763克，产率82％)；
(6)合成化合物P-078
取25毫升双颈圆底瓶并内置搅拌子与上接回流管，干燥后充入氮气，分别加入0.465克中间体5-4(1.0当量)与0.241克化合物H-4(1.1当量)，加入10毫升甲苯，并搅拌混合10分钟，加热回流并反应6小时，待其回温后加入10毫升水，接着用乙酸乙酯萃取，每次15毫升，萃取三次，所得到的萃取液依序加入硫酸镁干燥、过滤及旋干，粗产物以层析纯化(乙酸乙酯/己烷，1/20)，得到化合物P-078(0.580克，产率96％)。
元素分析：(C46H37N)理论值：C,91.50；H,6.18；N,2.32；实测值：C,91.47；H,6.22；N,2.31；HRMS(ESI)m/z(M+)：理论值：603.2926；实测值：603.2921。
实施例5
本实施例提供一种稠合三联苯化合物，具有下述式(P-219)所示的结构：
Figure BDA0002078734320000571
式(P-219)所示稠合三联苯化合物的合成路径如下所示：
Figure BDA0002078734320000572
式(P-219)所示稠合三联苯化合物的制备方法具体包括以下步骤：
以式(C)所示的化合物和苯硼酸为原料，依据实施例1中提供的合成方法，其不同之处在于，在步骤(5)中用化合物F-5替代苯硼酸，用化合物H-5替代化合物H-1，得到式(P-219)所示的稠合三联苯化合物(0.842克，产率78％)。
元素分析：(C41H33N)理论值：C,91.24；H,6.16；N,2.60；实测值：C,91.22；H,6.18；N,2.59；HRMS(ESI)m/z(M+)：理论值：539.2613；实测值：539.2618。
实施例6
本实施例提供一种稠合三联苯化合物，具有下述式(P-262)所示的结构：
Figure BDA0002078734320000581
式(P-262)所示稠合三联苯化合物的合成路径如下所示：
Figure BDA0002078734320000582
式(P-262)所示稠合三联苯化合物的制备方法具体包括以下步骤：
以式(C)所示的化合物和苯硼酸为原料，依据实施例1中提供的合成方法，其不同之处在于，在步骤(5)中用化合物F-6替代苯硼酸，用化合物H-6替代化合物H-1，得到式(P-262)所示的稠合三联苯化合物(1.133克，产率94％)。
元素分析：(C46H34O)理论值：C,91.66；H,5.69；实测值：C,91.67；H,5.65；HRMS(ESI)m/z(M+)：理论值：602.2610；实测值：602.2615。
实施例7
本实施例提供一种稠合三联苯化合物，具有下述式(P-371)所示的结构：
Figure BDA0002078734320000591
式(P-371)所示稠合三联苯化合物的合成路径如下所示：
Figure BDA0002078734320000592
式(P-371)所示稠合三联苯化合物的制备方法具体包括以下步骤：
步骤(1)-(3)同实施例1；
(4)合成中间体4-7
取250毫升双颈圆底瓶并内置搅拌子与上接回流管，干燥后充入氮气，加入2.200克中间体3-7(1.0当量)，加入50毫升乙醚并降温至0℃，搅拌混合10分钟，缓慢滴加甲基溴化镁(1.0mol/L)于15毫升乙醚溶液(3.0当量)中，加热回流并反应3小时，待其回温后用30毫升5％盐酸水溶液淬灭反应，接着用二氯甲烷萃取，每次25毫升，萃取三次，所得到的萃取液依序加入硫酸镁干燥、过滤及旋干，粗产物以层析纯化(乙酸乙酯/己烷，1/15)，得到中间体4’-7(1.794克，产率76％)；
取100毫升双颈圆底瓶并放入搅拌子与上接回流管，干燥后充入氮气，加入1.417克中间体4’-7(1.0当量)，分别加入30毫升苯与3毫升硫酸，加热回流并反应18小时，待其回温后加入10毫升水，接着用乙酸乙酯萃取，每次20毫升，萃取三次，所得到的萃取液依序加入硫酸镁干燥、过滤及旋干，粗产物以层析纯化(乙酸乙酯/己烷，1/25)，得到中间体4-7(1.485克，产率83％)；
(5)合成化合物P-371
同实施例1中步骤(5)，其不同之处在于，用化合物F-7替代苯硼酸，用化合物H-7替代化合物H-1，得到式(P-371)所示的稠合三联苯化合物(1.321克，产率85％)。
元素分析：(C60H40O)理论值：C,92.75；H,5.19；N,2.06；实测值：C,92.73；H,5.21；N,2.05；HRMS(ESI)m/z(M+)：理论值：776.3079；实测值：776.3074。
实施例8
本实施例提供一种稠合三联苯化合物，具有下述式(P-414)所示的结构：
Figure BDA0002078734320000601
式(P-414)所示稠合三联苯化合物的合成路径如下所示：
Figure BDA0002078734320000611
式(P-414)所示稠合三联苯化合物的制备方法具体包括以下步骤：
以式(C)所示的化合物和3,4-二甲基苯硼酸为原料，依据实施例1中提供的合成方法，其不同之处在于，在步骤(5)中用化合物F-8替代苯硼酸，用化合物H-8替代化合物H-1，得到式(P-414)所示的稠合三联苯化合物(0.509克，产率32％)。
元素分析：(C62H50)理论值：C,93.66；H,6.34；实测值：C,93.65；H,6.35；HRMS(ESI)m/z(M+)：理论值：794.3913；实测值：794.3907。
实施例9
本实施例提供一种稠合三联苯化合物，具有下述式(P-499)所示的结构：
Figure BDA0002078734320000621
式(P-499)所示稠合三联苯化合物的合成路径如下所示：
Figure BDA0002078734320000622
式(P-499)所示稠合三联苯化合物的制备方法具体包括以下步骤：
(1)合成中间体2-9
取100毫升双颈圆底瓶并内置搅拌子与上接回流管，干燥后充入氮气，分别加入5.757克的化合物C(1.0当量)、1.280克苯硼酸(1.05当量)、0.578克Pd(PPh3)4(5mol％)及2.649克碳酸钠(2.5当量)，加入40毫升甲苯和和4毫升水，并搅拌混合10分钟，加热回流并反应12小时，待其回温后加入3.876克3-(9-菲基)苯硼酸(1.3当量)，重新加热至回流并反应12小时，待其回温后加入30毫升水，接着用乙酸乙酯萃取，每次20毫升，萃取三次，所得到的萃取液依序加入硫酸镁干燥、过滤及旋干，粗产物以层析纯化(乙酸乙酯/己烷，1/20)，得到中间体2-9(4.044克，产率62％)；
步骤(2)-(5)同实施例1，其不同之处在于，在步骤(5)中用化合物F-9替代苯硼酸，用化合物H-9替代化合物H-1，得到式(P-499)所示的稠合三联苯化合物(1.134克，产率69％)。
元素分析：(C61H43NS)理论值：C,89.12；H,5.27；N,1.70；实测值：C,89.16；H,5.25,N,1.67；HRMS(ESI)m/z(M+)：理论值：821.3116；实测值：821.3109。
实施例10
本实施例提供一种稠合三联苯化合物，具有下述式(P-537)所示的结构：
Figure BDA0002078734320000631
式(P-537)所示稠合三联苯化合物的合成路径如下所示：
Figure BDA0002078734320000641
式(P-537)所示稠合三联苯化合物的制备方法具体包括以下步骤：
步骤(1)-(4)同实施例1；
(5)取25毫升双颈圆底瓶并内置搅拌子与上接回流管，干燥后充入氮气，分别加入0.936克中间体4-10(1.0当量)与0.368克化合物F-10(1.1当量)，加入10毫升甲苯，并搅拌混合10分钟，加热回流并反应6小时，待其回温后加入0.588克化合物H-10(1.1当量)，重新加热回流并反应6小时，待其回温后加入10毫升水，接着用乙酸乙酯萃取，每次15毫升，萃取三次，所得到的萃取液依序加入硫酸镁干燥、过滤及旋干，粗产物以层析纯化(乙酸乙酯/己烷，1/20)，得到化合物P-537(1.349克，产率91％)。
元素分析：(C56H40N2)理论值：C,90.78；H,5.44；N,3.78；实测值：C,90.77；H,5.41；N,2.82；HRMS(ESI)m/z(M+)：理论值：710.3191；实测值：740.3183。
实施例11
本实施例提供一种稠合三联苯化合物，具有下述式(P-573)所示的结构：
Figure BDA0002078734320000651
式(P-573)所示稠合三联苯化合物的合成路径如下所示：
Figure BDA0002078734320000652
式(P-573)所示稠合三联苯化合物的制备方法具体包括以下步骤：
以式(C)所示的化合物和苯硼酸为原料，依据实施例1中提供的合成方法，其不同之处在于，在步骤(5)中用化合物F-11替代苯硼酸，用化合物H-11替代化合物H-1，得到式(P-573)所示的稠合三联苯化合物(0.932克，产率65％)。
元素分析：(C54H40O2)理论值：C,90.47；H,5.62；N,3.91；实测值：C,90.47；H,5.65,N,3.88；HRMS(ESI)m/z(M+)：理论值：716.3191；实测值：716.3196。
实施例12
本实施例提供一种有机电致发光器件，如图3所示，包括从下向上依次层叠设置的阳极1、空穴注入层2、空穴传输层3、发光层4、电子传输层5、电子注入层6和阴极7。
有机电致发光器件中阳极1选用ITO材料；
空穴注入层2材料选用如下所述结构的化合物HAT(CN)6：
Figure BDA0002078734320000661
空穴传输层3材料选用如下所述结构的化合物NPB：
Figure BDA0002078734320000662
有机电致发光器件中发光层4以主体材料和客体发光染料共掺杂形成，其中主体材料选用实施例1制备的化合物P-009，客体材料选用化合物BD，主体材料和客体材料掺杂的质量比为100:3，化合物BD的化学结构如下所示：
Figure BDA0002078734320000663
电子传输层5材料选用如下所述结构的化合物TPBI：
Figure BDA0002078734320000671
电子注入层6以下述所示结构的化合物BCP与电子注入材料LiF共掺杂形成，其中BCP与LiF掺杂的质量比为100:3：
Figure BDA0002078734320000672
阴极7选用金属Al。
有机致电发光器件的制备方法如下：
基板清理：将涂布了ITO透明基板在商用清洗剂中超声处理，在去离子水中冲洗，在丙酮：乙醇混合溶剂(体积比1：1)中超声除油，在洁净环境下烘烤至完全除去水份，然后用紫外光和臭氧清洗；
有机层制备：将ITO透明基板转移至蒸镀设备中，依次蒸镀30nm空穴注入层、40nm空穴传输层、40nm有机发光层、40nm电子传输层、1nm电子注入层、150nm阴极。
实施例13
本实施例提供一种有机电致发光器件，与实施例12中提供有机电致发光器件的区别仅在于：发光层主体材料选用实施例2制备的化合物P-040。
实施例14
本实施例提供一种有机电致发光器件，与实施例12中提供有机电致发光器件的区别仅在于：发光层主体材料选用实施例3制备的化合物P-041。
实施例15
本实施例提供一种有机电致发光器件，与实施例12中提供有机电致发光器件的区别仅在于：发光层主体材料选用实施例4制备的化合物P-078。
实施例16
本实施例提供一种有机电致发光器件，与实施例12中提供有机电致发光器件的区别仅在于：发光层主体材料选用实施例5制备的化合物P-219。
实施例17
本实施例提供一种有机电致发光器件，与实施例12中提供有机电致发光器件的区别仅在于：发光层主体材料选用实施例6制备的化合物P-262。
实施例18
本实施例提供一种有机电致发光器件，与实施例12中提供有机电致发光器件的区别仅在于：发光层主体材料选用实施例7制备的化合物P-371。
实施例19
本实施例提供一种有机电致发光器件，与实施例12中提供有机电致发光器件的区别仅在于：发光层主体材料选用实施例8制备的化合物P-414。
实施例20
本实施例提供一种有机电致发光器件，与实施例12中提供有机电致发光器件的区别仅在于：发光层主体材料选用实施例9制备的化合物P-499。
实施例21
本实施例提供一种有机电致发光器件，与实施例12中提供有机电致发光器件的区别仅在于：发光层主体材料选用如下所示的化合物BH：
Figure BDA0002078734320000691
且
客体材料选用实施例10制备的化合物P-537。
实施例22
本实施例提供一种有机电致发光器件，与实施例12中提供有机电致发光器件的区别仅在于：发光层主体材料选用实施例11制备的化合物P-573。
对比例1
本实施例提供一种有机电致发光器件，与实施例12中提供有机电致发光器件的区别仅在于：发光层主体材料选用如实施例21中所示的化合物BH。
测试例1
测定热分解温度温度：
使用热重分析仪(TGA)对实施例1-11中的化合物材料进行热分解温度测试，测试范围室温至600℃，升温速率10℃/min，氮气氛围下，重量损失5％的温度定义为热分解温度(Td)，测定结果如表1所示：
表1
化合物 009 040 041 078 219 262 371 414 499 537 573
T<sub>d</sub>(℃) 391 398 384 403 373 387 388 403 395 411 379
由上述测试得到的各化合物材料的热分解温度可知，实施例1-11制得的化合物均具有较高的热分解温度(373-411℃)，可以保证材料在器件中保持优异的热稳定性，使得在器件制备过程中不易分解破坏，使用寿命长。
测试例2
对实施例12-22和对比例1中的所提供的有机电致发光器件进行测试，器件的电流、电压、亮度、发光光谱等特性采用PR 650光谱扫描亮度计和Keithley K 2400数字源表系统同步测试，结果见表2。
表2
Figure BDA0002078734320000701
由表2中的测试数据可知，实施例12-22与对比例1相比，采用本申请实施例1-11中的化合物作为有机电致发光器件发光层的主体/客体材料可以有效降低器件的工作电压，同时能够提升器件的发光效率。
显然，上述实施例仅仅是为清楚地说明所作的举例，而并非对实施方式的限定。对于所属领域的普通技术人员来说，在上述说明的基础上还可以做出其它不同形式的变化或变动。这里无需也无法对所有的实施方式予以穷举。而由此所引伸出的显而易见的变化或变动仍处于本发明创造的保护范围之中。

Claims (10)

1.一种稠合三联苯化合物，其特征在于，具有式(I)所示的结构：
Figure FDA0003527819720000011
其中，R1-R2彼此独立地选自C1-C60未取代的烷基、C4-C60未取代的芳基；
R3-R10彼此独立地选自氢、C1-C60未取代的烷基、C4-C60未取代的芳基；
Ar1、Ar2彼此独立地选自C4-C60未取代的芳基、C3-C60未取代的杂芳基。
2.一种稠合三联苯化合物，其特征在于，具有如下任一所示的分子结构：
Figure FDA0003527819720000012
Figure FDA0003527819720000021
Figure FDA0003527819720000031
Figure FDA0003527819720000041
Figure FDA0003527819720000051
Figure FDA0003527819720000061
Figure FDA0003527819720000071
Figure FDA0003527819720000081
Figure FDA0003527819720000091
Figure FDA0003527819720000101
Figure FDA0003527819720000111
Figure FDA0003527819720000121
Figure FDA0003527819720000131
Figure FDA0003527819720000141
Figure FDA0003527819720000151
Figure FDA0003527819720000161
Figure FDA0003527819720000171
Figure FDA0003527819720000181
Figure FDA0003527819720000191
Figure FDA0003527819720000201
Figure FDA0003527819720000211
Figure FDA0003527819720000221
Figure FDA0003527819720000231
Figure FDA0003527819720000241
Figure FDA0003527819720000251
Figure FDA0003527819720000261
Figure FDA0003527819720000271
Figure FDA0003527819720000281
Figure FDA0003527819720000291
Figure FDA0003527819720000301
Figure FDA0003527819720000311
Figure FDA0003527819720000321
Figure FDA0003527819720000331
Figure FDA0003527819720000341
Figure FDA0003527819720000351
Figure FDA0003527819720000361
Figure FDA0003527819720000371
Figure FDA0003527819720000381
Figure FDA0003527819720000391
3.一种如权利要求1或2所述的稠合三联苯化合物的制备方法，其特征在于，
所述式(I)所示化合物的合成步骤如下所示：以式(C)所示的化合物为起始原料，经偶联反应得到中间体2；中间体2经过脱水反应得到中间体3；中间体3经过加成反应和取代反应得到中间体4；中间体4经偶联反应，得到式(I)所示的化合物；
所述式(I)所示化合物的合成路线如下所示：
Figure FDA0003527819720000392
；
其中R1-R10、Ar1、Ar2的定义同权利要求1或2中相应化合物中的定义。
4.根据权利要求3所述的稠合三联苯化合物的制备方法，其特征在于，
所述式(C)所示化合物的合成步骤如下所示：以式(A)所示的化合物和碘为起始原料，经过卤代反应得到式(B)所示的化合物；式(B)所示的化合物经过氧化反应得到式(C)所示化合物；
经过脱水反应得到中间体3；中间体3经过加成反应和取代反应得到中间体4；中间体4经偶联反应，得到式(I)所示的化合物，
所述式(C)所示化合物的合成路线如下所示：
Figure FDA0003527819720000401
5.根据权利要求4所述的稠合三联苯化合物的制备方法，其特征在于，
由式(C)所示的化合物得到中间体2的步骤如下所示：以式(C)所示的化合物和式(D)所示的化合物为原料，经过偶联反应得到中间体1；中间体1和式(E)所示的化合物经过偶联反应得到中间体2；
由式(C)所示的化合物得到中间体2的合成路线如下所示：
Figure FDA0003527819720000402
。
6.根据权利要求3所述的稠合三联苯化合物的制备方法，其特征在于，由中间体4得到式(I)所示的化合物的步骤如下所示：以中间体4和式(F)或(G)所示的化合物为原料，经过偶联反应得到中间体5；中间体5和式(H)或(J)所示的化合物，经过偶联反应得到式(I)所示的化合物；
由中间体4得到式(I)所示的化合物的合成路线如下所示：
Figure FDA0003527819720000411
。
7.一种权利要求1-2任一所述的稠合三联苯化合物作为有机电致发光材料的用途。
8.一种有机电致发光器件，其特征在于，所述有机电致发光器件的至少一个功能层中含有权利要求1-2任一所述的稠合三联苯化合物。
9.根据权利要求8所述的有机电致发光器件，其特征在于，所述功能层为发光层。
10.根据权利要求9所述的有机电致发光器件，其特征在于，所述发光层材料包括主体材料和客体材料，所述主体材料或所述客体材料为所述稠合三联苯化合物。
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