WO2020228359A1 - 一种含四苯基苯的有机发光材料及制备与应用 - Google Patents

一种含四苯基苯的有机发光材料及制备与应用 Download PDF

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WO2020228359A1
WO2020228359A1 PCT/CN2020/070205 CN2020070205W WO2020228359A1 WO 2020228359 A1 WO2020228359 A1 WO 2020228359A1 CN 2020070205 W CN2020070205 W CN 2020070205W WO 2020228359 A1 WO2020228359 A1 WO 2020228359A1
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tetraphenylbenzene
material containing
emitting material
organic light
organic
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唐本忠
秦安军
韩鹏博
马东阁
徐增
赵祖金
胡蓉蓉
王志明
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South China University of Technology SCUT
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Priority to KR1020217040816A priority patent/KR20220007891A/ko
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Definitions

  • the invention belongs to the field of organic photoelectric materials, and specifically relates to an organic luminescent material containing tetraphenylbenzene and its preparation and application.
  • organic optoelectronic materials have been widely used in the field of organic electroluminescent diodes. Due to their important scientific research value and broad commercial application prospects, they have become a rapidly growing field in materials science. . Exploring and developing organic luminescent materials with better performance, high luminous efficiency, and adjustable emission wavelength is an urgent problem for researchers to solve. However, the development of high-efficiency luminescent materials is quite difficult, because traditional materials will quench their luminescence in the aggregate state.
  • the primary purpose of the present invention is to provide an organic light-emitting material containing tetraphenylbenzene.
  • the molecular structure of tetraphenylbenzene is simple, which is convenient for chemical modification and functionalization.
  • the invention uses tetraphenylbenzene to construct a material with high solid-state luminous efficiency. Combining tetraphenylbenzene with hole transport materials and electron transport materials can obtain luminescent materials with high solid-state luminous efficiency and dual-stage transport characteristics. These materials have shown excellent performance in the field of organic optoelectronics.
  • tetraphenylbenzene is a functional group with simple structure and excellent performance with aggregation-induced luminescence characteristics, and has broad application prospects in the construction of organic photoelectric materials.
  • Another object of the present invention is to provide a method for preparing the above-mentioned tetraphenylbenzene-containing organic light-emitting material.
  • Another object of the present invention is to provide the application of the above-mentioned tetraphenylbenzene-containing organic light-emitting material in organic electroluminescent devices.
  • R 1 is an electron donating group of an aromatic ring derivative
  • R 2 is an electron withdrawing group of an aromatic ring derivative
  • R 1 is one of the following 1-20 substituents:
  • R' is a hydrogen atom, tert-butyl group, methoxy group, cyano group, fluorine atom or alkyl chain, n is a natural number from 0 to 10, and * is the position of substitution;
  • the R 2 is one of the following a to o substituents:
  • R" is a hydrogen atom, a tert-butyl group, a methoxy group, a cyano group, a fluorine atom or an alkyl chain, n is a natural number from 0 to 10, and * is a substitution position.
  • alkyl chain refers to a linear, branched or cyclic alkyl chain having 1 to 20 carbon atoms, or one or more carbon atoms are replaced by oxygen atoms, alkenyl, alkynyl, aryl, or carbonyl groups. , Hydroxy, amino, carboxyl, cyano, nitro, or ester group substituted alkyl chain, or one or more hydrogen atoms replaced by fluorine, chlorine, bromine, or iodine atoms.
  • the method for preparing the above-mentioned tetraphenylbenzene-containing organic light-emitting material includes the following steps:
  • different electron donating and withdrawing groups are connected to tetraphenylbenzene, so as to well adjust the carrier transport performance of tetraphenylbenzene derivatives.
  • the resulting structure is twisted, and strong ⁇ - ⁇ interaction is not easily generated in the aggregate state; in addition, this twisted molecular structure is beneficial to increase the triplet energy level of the material, so that the resulting material can be used as a luminescent host material of different light colors.
  • the characterization data of the organic electroluminescent device can show that the tetraphenylbenzene-containing organic luminescent material of the present invention can not only be used as a light-emitting layer, but also can be used as a phosphorescent host material, thereby preparing a good photoelectric performance, simple structure, and low cost.
  • Electroluminescent devices have broad application prospects in the field of organic electroluminescence, and are expected to be widely used in flat panel displays and solid-state lighting.
  • the present invention has the following advantages and beneficial effects:
  • the tetraphenylbenzene-containing organic light-emitting material of the present invention has the characteristics of high-efficiency solid-state light emission and bipolarity, and can produce high-efficiency, low-efficiency roll-off, non-doped blue organic electroluminescence devices;
  • the tetraphenylbenzene-containing organic light-emitting material of the present invention has a simple synthesis method, easy-to-obtain raw materials, high yield, and the obtained material has a stable structure and simple storage;
  • the tetraphenylbenzene-containing organic light-emitting material of the present invention has excellent electroluminescence performance and can be widely used in fields such as organic electroluminescence.
  • Fig. 1 is a J-V-L curve diagram of an undoped blue OLEDs device prepared by using the organic electroluminescent material containing tetraphenylbenzene in Example 1;
  • Example 2 is a graph showing the change in efficiency of non-doped blue OLEDs prepared by using the organic electroluminescent material containing tetraphenylbenzene in Example 1 as a function of brightness;
  • Example 3 is a J-V-L curve diagram of a mixed white light OLEDs device prepared by using the organic electroluminescent material containing tetraphenylbenzene in Example 1;
  • Example 4 is a graph of the efficiency of the mixed white light OLEDs device prepared by using the organic electroluminescent material containing tetraphenylbenzene in Example 1 as a function of brightness;
  • FIG. 5 is a J-V-L curve diagram of a non-doped blue OLED device prepared by using the organic electroluminescent material containing tetraphenylbenzene in Example 2;
  • Example 6 is a graph of the efficiency of non-doped blue OLEDs prepared by using the organic electroluminescent material containing tetraphenylbenzene in Example 2 as a function of brightness.
  • the synthetic route is as follows:
  • the synthetic route is as follows:
  • the synthetic route is as follows:
  • the synthetic route is as follows:
  • the synthetic route is as follows:
  • the synthetic route is as follows:
  • the synthetic route is as follows:
  • FIG. 1 is a JVL curve diagram of a non-doped blue OLED device prepared by using the organic electroluminescent material containing tetraphenylbenzene in Example 1. It can be seen from the figure that the maximum brightness of the non-doped device based on TPA-TPB-CN is high and the starting voltage is low, which is 3945cd/m 2 , 2.8V.
  • Example 2 is a graph showing the variation of the efficiency of the non-doped deep blue OLED device prepared by using the organic electroluminescent material containing tetraphenylbenzene in Example 1 with the brightness. It can be seen from the figure that the non-doped device based on TPA-TPB-CN has good efficiency and reduced efficiency, and its maximum external quantum efficiency is 6.8%; when the brightness is 1000cd/m 2 , the external quantum efficiency is still maintained At 6.33%; the emission wavelength is at 446nm.
  • FIG. 3 is a JVL curve diagram of a mixed white light OLEDs device using the organic electroluminescent material (TPA-TPB-CN) containing tetraphenylbenzene in Example 1. It can be seen from the figure that the maximum brightness of the obtained device is high and the starting voltage is low, 51393cd/m 2 , 2.8V.
  • FIG. 4 is a graph showing the efficiency of the two-color white light OLEDs device using the organic electroluminescent material (TPA-TPB-CN) containing tetraphenylbenzene in Example 1 as a function of brightness. It can be seen from the figure that the obtained two-color white light device has good efficiency and reduced efficiency. Its maximum power efficiency and external quantum efficiency are 60.7lm/W and 19.1% respectively; when the brightness is 1000cd/m 2 , the external quantum efficiency The efficiency is 18.7%.
  • Example 5 is a JVL curve diagram of non-doped blue OLEDs prepared by using the organic electroluminescent material containing tetraphenylbenzene in Example 2. It can be seen from the figure that the maximum brightness and starting voltage of the obtained device are 709 cd/m 2 and 3.4V respectively.
  • Example 6 is a graph of the efficiency of non-doped blue OLEDs prepared by using the organic electroluminescent material containing tetraphenylbenzene in Example 2 as a function of brightness. It can be seen from the figure that the obtained devices all have good efficiency and the efficiency is reduced.
  • the maximum external quantum efficiency is 4.17%; when the brightness is 100 cd/m 2 , the external quantum efficiency is 3.80%.
  • the present invention obtains molecules with both AIE performance and deep blue light emission by attaching different electron-donating groups to tetraphenylbenzene, and uses such materials as the light-emitting layer to prepare non-doped deep blue OLEDs.
  • High efficiency and low efficiency roll-off; non-doped OLEDs with simple structure based on such materials have lower starting voltage, higher efficiency, and a smaller degree of efficiency roll-off; at the same time,
  • Such materials are used as the main body to prepare two-color white light devices, and the obtained devices have high efficiency and low roll-off.
  • this type of material has a very broad application prospect in the field of organic electroluminescence.

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Abstract

本发明属于有机光电材料领域，公开了一种含四苯基苯的有机发光材料及制备与应用。所述含四苯基苯的有机发光材料具有式I所示的结构式，其中，R1为芳香环衍生物给电子基团，R2为芳香环衍生物吸电子基团。其制备方法为：以1,4-二溴-2,5-三联苯和R2取代的苯硼酸为原料，通过Suzuki反应得到含R2的芳香环化合物；然后在四三苯基膦钯催化剂的作用下，含R2的芳香环化合物与R1取代的苯硼酸或硼酸酯进行反应，得到含四苯基苯的有机发光材料。本发明的含四苯基苯的有机发光材料具有高效固态发光、双极性的特征，可制备出高效率、低程度效率滚降、非掺杂蓝光有机电致发光器件。

Description

一种含四苯基苯的有机发光材料及制备与应用 技术领域
本发明属于有机光电材料领域，具体涉及一种含四苯基苯的有机发光材料及制备与应用。
背景技术
随着有机电子产业的兴起和蓬勃发展，有机光电材料在有机电致发光二极管领域得到广泛应用，由于其重要的科学研究价值和广阔的商业应用前景，目前已成为材料科学中一个快速增长的领域。探索和开发性能更优、发光效率高、发射波长可调的有机发光材料是科研人员急需解决的难题。但是高效的发光材料的开发是相当难的，这是因为传统的材料在聚集态下会导致其发光淬灭。
发明内容
针对以上现有技术存在的缺点和不足之处，本发明的首要目的在于提供一种含四苯基苯的有机发光材料。四苯基苯分子结构简单，便于化学修饰和功能化。本发明利用四苯基苯构筑了高固态发光效率的材料。将四苯基苯与空穴传输材料、电子传输材料结合，能够得到同时具有高固态发光效率和双级传输特性的发光材料。这些材料在有机光电领域表现出了优异性能。总体来说，四苯基苯是一个结构简单，性能优异的具有聚集诱导发光特性的功能基团，在有机光电材料的构筑中有广阔的应用前景。
本发明的另一目的在于提供上述含四苯基苯的有机发光材料的制备方法。
本发明的再一目的在于提供上述含四苯基苯的有机发光材料在有机电致发光器件中的应用。
本发明目的通过以下技术方案实现：
一种含四苯基苯的有机发光材料，具有式I所示的结构式：
Figure PCTCN2020070205-appb-000001
其中，R 1为芳香环衍生物给电子基团，R 2为芳香环衍生物吸电子基团。
进一步地，所述R 1为以下1～20取代基中的一种：
Figure PCTCN2020070205-appb-000002
其中，R＇为氢原子、叔丁基、甲氧基、氰基、氟原子或烷基链，n为0～10的自然数，*为取代位置；
所述R 2为以下a～o取代基中的一种：
Figure PCTCN2020070205-appb-000003
其中，R″为氢原子、叔丁基、甲氧基、氰基、氟原子或烷基链，n为0～10的自然数，*为取代位置。
进一步地，所述烷基链指具有1～20个碳原子的直链、支链或者环状烷基链，或一个或多个碳原子被氧原子、烯基、炔基、芳基、羰基、羟基、氨基、羧基、氰基、硝基或者酯基取代的烷基链，或一个或多个氢原子被氟原子、氯原子、溴原子、碘原子取代的烷基链。
上述含四苯基苯的有机发光材料的制备方法，包含以下步骤：
以1,4-二溴-2,5-三联苯和R 2取代的苯硼酸为原料，通过Suzuki反应得到含R 2的芳香环化合物；然后在四三苯基膦钯催化剂的作用下，含R 2的芳香环化合物与R 1取代的苯硼酸或硼酸酯进行反应，得到含四苯基苯的有机发光材料；上述制备方法的反应式如下式所示：
Figure PCTCN2020070205-appb-000004
上述含四苯基苯的有机发光材料在有机电致发光器件中的应用。
本发明通过在四苯基苯接上不同的给、吸电子基团，从而很好的调节四苯基苯衍生物的载流子传输性能。所得的结构扭曲，聚集状态下不易产生强的π-π相互作用；此外，这种扭曲的分子结构有利于提高材料的三线态能级，从而所得材料可以用作不同光色的发光主体材料。有机电致发光器件的表征数据可以表明，本发明的含四苯基苯的有机发光材料不仅可以作为发光层，还可以作为磷光主体材料使用，从而制备得到光电性能良好、结构简单、成本低廉的电致发光器件，在有机电致发光领域具有广泛的应用前景，有望在平板显示和固态照明等领域得到广泛应用。
相对于现有技术，本发明具有如下优点及有益效果：
(1)本发明的含四苯基苯的有机发光材料具有高效固态发光、双极性的特征，可制备出高效率、低程度效率滚降、非掺杂蓝光有机电致发光器件；
(2)本发明的含四苯基苯的有机发光材料合成方法简单、原料易得、产率较高，得到的材料结构稳定，存放简单；
(3)本发明的含四苯基苯的有机发光材料，电致发光性能优异，可以广泛应用于有机电致发光等领域。
附图说明
图1为利用实施例1含四苯基苯的有机电致发光材料制备得到的非掺杂蓝光OLEDs器件的J-V-L曲线图；
图2为利用实施例1含四苯基苯的有机电致发光材料制备得到的非掺杂蓝光OLEDs器件的效率随亮度变化的曲线图；
图3为利用实施例1含四苯基苯的有机电致发光材料制备得到的混合白光OLEDs器件的J-V-L曲线图；
图4为利用实施例1含四苯基苯的有机电致发光材料制备得到的混合白光OLEDs器件的效率随亮度变化的曲线图；
图5为利用实施例2含四苯基苯的有机电致发光材料制备得到的非掺杂蓝光OLEDs器件的J-V-L曲线图；
图6为利用实施例2含四苯基苯的有机电致发光材料制备得到的非掺杂蓝光OLEDs器件的效率随亮度变化的曲线图。
具体实施方式
下面结合实施例及附图对本发明作进一步详细的描述，但本发明的实施方式不限于此。
实施例1
本实施例含四苯基苯的有机电致发光材料(TPA-TPB-CN)的制备：
Figure PCTCN2020070205-appb-000005
合成路线如下：
Figure PCTCN2020070205-appb-000006
(1)将对溴三联苯(化合物1)(6g,15.5mmol)、4-氰基苯硼酸(化合物2)(2.50g,17.0mmol)、无水碳酸钾(6.4g,46.5mmol)和Pd(PPh 3) 4(895mg,0.8mmol)加入250mL反应瓶，在氮气保护下，加入105mLTHF和15mL水，回流过夜，反应冷却后经二氯甲烷萃取，浓缩后做粉过柱，得到白色固体3，产率73％；
(2)将中间体3(2.136g,1.5mmol)、4-苯硼酸三苯胺(化合物4)(1.6g,3.9mmol)、无水碳酸钾(1.616g,11.7mmol)和Pd(PPh 3) 4(225mg,0.195mmol)加 入250mL反应瓶，在氮气保护下，加入10mL THF和5mL水，回流过夜，反应冷却后经二氯甲烷萃取，浓缩后做粉过柱，得到白色固体TPA-TPB-CN，产率85％；产物鉴定数据如下：
1H NMR(MHz):δ(TMS,ppm):7.59(s,1H),7.55(t,1H),7.53(t,1H),7.51(d,3H),7.48(d,2H),7.37(t,1H),7.35(t,1H),7.26(m,14H),7.22(m,2H),7.10(m,6H),7.03(m,2H)。
实施例2
本实施例含四苯基苯的有机电致发光材料(Cz-TPB-CN)的制备
Figure PCTCN2020070205-appb-000007
合成路线如下：
Figure PCTCN2020070205-appb-000008
将中间体3(2.136g,1.5mmol)、4-硼酸咔唑(化合物5)(1.119g,3.9mmol)、无水碳酸钾(1.616g,11.7mmol)和Pd(PPh 3) 4(225mg,0.195mmol)加入250mL反应瓶，在氮气保护下，加入10mLTHF和5mL水，回流过夜，反应冷却后经二氯甲烷萃取，浓缩后做粉过柱，得到白色固体Cz-TPB-CN，产率86％；产物鉴定数据如下：
1H NMR(500MHz,CD 2Cl 2),δ(TMS,ppm):8.16(m,1H),8.14(m,1H),7.69(s,1H),7.58(d,2H),7.56(m,1H),7.47(d,4H),7.45-7.38(m,6H),7.35-7.25(m,12H)。
实施例3
本实施例含四苯基苯的有机电致发光材料(3PhCz-TPB-CN)的制备
Figure PCTCN2020070205-appb-000009
合成路线如下：
Figure PCTCN2020070205-appb-000010
将中间体3(2.136g,1.5mmol)、化合物6(1.415g,3.9mmol)、无水碳酸钾(1.616g,11.7mmol)和Pd(PPh 3) 4(225mg,0.195mmol)加入250mL反应瓶，在氮气保护下，加入10mL THF和5mL水，回流过夜，反应冷却后经二氯甲烷萃取，浓缩后做粉过柱，得到白色固体3PhCz-TPB-CN，产率84％；产物鉴定数据如下：
1H NMR(500MHz,CDCl 3),δ(TMS,ppm):8.35(d,1H),8.18(m,1H),7.59-7.66(m,8H),7.50(d,3H),7.47(m,4H),7.27-7.45(d,13H),7.29(m,2H)。
实施例4
本实施例含四苯基苯的有机电致发光材料(AD-TPB-CN)的制备
Figure PCTCN2020070205-appb-000011
合成路线如下：
Figure PCTCN2020070205-appb-000012
将中间体3(2.136g,1.5mmol)、化合物7(1.283g,3.9mmol)、无水碳酸钾(1.616g,11.7mmol)和Pd(PPh 3) 4(225mg,0.195mmol)加入250mL反应瓶，在氮气保护下，加入10mL THF和5mL水，回流过夜，反应冷却后经二氯甲烷萃取，浓缩后做粉过柱，得到白色固体AD-TPB-CN，产率87％；产物鉴定数据如下：
1H NMR(400MHz,):δ(TMS,ppm):7.69(s,1H),7.58(d,2H),7.56(t,1H),7.47(t,4H),7.40(t,1H),7.38(t,1H),7.33-7.25(m,10H),7.22(d,1H),7.20(s,1H),6.97(m,4H),6.26(m,2H),1.66(m,6H)。
实施例5
本实施例含四苯基苯的有机电致发光材料(CzPh-TPB-CN)的制备
Figure PCTCN2020070205-appb-000013
合成路线如下：
Figure PCTCN2020070205-appb-000014
将中间体3(2.136g,1.5mmol)、化合物8(1.416g,3.9mmol)、无水碳酸 钾(1.616g,11.7mmol)和Pd(PPh 3) 4(225mg,0.195mmol)加入250mL反应瓶，在氮气保护下，加入10mL THF和5mL水，回流过夜，反应冷却后经二氯甲烷萃取，浓缩后做粉过柱，得到白色固体CzPh-TPB-CN，产率89％。
实施例6
本实施例含四苯基苯的有机电致发光材料(DPA-TPB-CN)的制备
Figure PCTCN2020070205-appb-000015
合成路线如下：
Figure PCTCN2020070205-appb-000016
将中间体3(2.136g,1.5mmol)、化合物9(1.127g,3.9mmol)、无水碳酸钾(1.616g,11.7mmol)和Pd(PPh 3) 4(225mg,0.195mmol)加入250mL反应瓶，在氮气保护下，加入10mLTHF和5mL水，回流过夜，反应冷却后经二氯甲烷萃取，浓缩后做粉过柱，得到白色固体DPA-TPB-CN，产率88％。
实施例7
本实施例含四苯基苯的有机电致发光材料(Cz-TPB-3Q)的制备：
Figure PCTCN2020070205-appb-000017
合成路线如下：
Figure PCTCN2020070205-appb-000018
(1)将对溴三联苯(化合物1)(5.43g,14.0mmol)、咔唑苯硼酸(化合物10)(4.82g,16.8mmol)、无水碳酸钾(5.8g,42.0mmol)和Pd(PPh 3) 4(809mg,0.7mmol)加入250mL反应瓶，在氮气保护下，加入90mLTHF和21mL水，回流过夜，反应冷却后经二氯甲烷萃取，浓缩后做粉过柱，得到白色固体11，产率91％；
(2)将中间体11(1.10g,2mmol)、4硼酸-1,3,5三苯基三嗪(化合物12)(847mg,2.4mmol)、无水碳酸钾(828mg,6.0mmol)和Pd(PPh 3) 4(116mg,0.10mmol)加入125mL反应瓶，在氮气保护下，加入14mLTHF和3mL水，回流过夜，反应冷却后经二氯甲烷萃取，浓缩后做粉过柱，得到白色固体TPA-TPB-3Q，产率84％。
实施例8
本实施例测试含四苯基苯的有机电致发光材料(TPA-TPB-CN)的蓝光OLEDs器件性能：
利用实施例1制备得到的含四苯基苯的有机电致发光材料TPA-TPB-CN(固态荧光量子产率＝93.2％)作为发光材料制备得到非掺杂蓝光器件，并对其器件性能进行测试表征，结果见图1～2。
器件结构：ITO/HAT-CN(5nm)/TAPC(50nm)/TCTA(5nm)/TPA-TPB-CN(20nm)/TmPyPB(40nm)/LiF(1nm)/Al。
图1为利用实施例1含四苯基苯的有机电致发光材料制备得到的非掺杂蓝光OLEDs器件的J-V-L曲线图。从图中可以看出，基于TPA-TPB-CN的非掺杂器件的最大亮度高并且启动电压低，为3945cd/m 2，2.8V。
图2为利用实施例1含四苯基苯的有机电致发光材料制备得到的非掺杂深蓝光OLED器件的效率随亮度变化的曲线图。从图中可以看出，基于TPA-TPB-CN的非掺杂器件具有良好的效率且效率滚降低，其最大外量子效率为6.8％；当亮度为1000cd/m 2时，外量子效率还维持在6.33％；发光波长在446nm。
实施例9
本实施例测试含四苯基苯的有机电致发光材料(TPA-TPB-CN)的混合白光OLEDs器件性能：
利用实施例1制备得到的含四苯基苯的有机电致发光材料TPA-TPB-CN作为蓝光发光层和黄色磷光主体制备得到双色白光器件，并对其器件进行测试表征，结果见图3～4。
器件结构：ITO/HAT-CN(5nm)/TAPC(50nm)/TCTA(5nm)/TPA-TPB-CN(8nm)/TPA-TPB-CN:3％PO-01(12nm)/TmPyPB(40nm)/LiF(1nm)/Al。
图3为利用实施例1含四苯基苯的有机电致发光材料(TPA-TPB-CN)的混合白光OLEDs器件的J-V-L曲线图。从图中可以看出，所获得器件最大亮度高并且启动电压低，为51393cd/m 2，2.8V。
图4为利用实施例1含四苯基苯的有机电致发光材料(TPA-TPB-CN)的双色白光OLEDs器件的效率随亮度变化的曲线图。从图中可以看出，获得的双色白光器件具有良好的效率且效率滚降低，其最大功率效率和外量子效率分别为60.7lm/W，19.1％；当亮度为1000cd/m 2时，外量子效率为18.7％。
实施例10
本实施例测试含四苯基苯的有机电致发光材料(Cz-TPB-CN)的非掺杂深蓝光OLEDs器件性能：
利用实施例2制备得到的含四苯基苯的有机电致发光材料Cz-TPB-CN(固 态荧光量子产率＝99.9％)作为发光材料制备得到非掺杂蓝光器件，并对其器件进行测试表征，结果见图5～6。
器件结构：ITO/HAT-CN(5nm)/TAPC(50nm)/mCP(5nm)/Cz-TPB-CN(20nm)/TmPyPB(40nm)/LiF(1nm)/Al。
图5为利用实施例2含四苯基苯的有机电致发光材料制备得到非掺杂蓝光OLEDs器件的J-V-L曲线图。从图中可以看出，所得到的器件的最大亮度和启动电压分别为709cd/m 2，3.4V。
图6为利用实施例2含四苯基苯的有机电致发光材料制备得到的非掺杂蓝光OLEDs器件的效率随亮度变化的曲线图。从图中可以看出，所获得的器件都具有良好的效率且效率滚降低，其最大外量子效率为4.17％；当亮度为100cd/m 2时，外量子效率为3.80％。
上述数据表明，本发明通过在四苯基苯上接上不同的给电子基团，获得同时具有AIE性能和深蓝发光的分子，将这类材料作为发光层制备出的非掺杂深蓝光OLEDs器件效率高，效率滚降程度较小；基于这类材料制备出的结构简单的非掺杂OLEDs器件，具有更低的启动电压，较高的效率，且效率滚降程度更小；同时也可以将这类材料用作主体制备双色白光器件，所获得器件效率高，滚降小。总之，这类材料在有机电致发光领域有很广阔的应用前景。
上述实施例为本发明较佳的实施方式，但本发明的实施方式并不受上述实施例的限制，其它的任何未背离本发明的精神实质与原理下所作的改变、修饰、替代、组合、简化，均应为等效的置换方式，都包含在本发明的保护范围之内。

Claims (5)

  1. 一种含四苯基苯的有机发光材料，其特征在于所述含四苯基苯的有机发光材料具有式I所示的结构式：
    Figure PCTCN2020070205-appb-100001
    其中，R 1为芳香环衍生物给电子基团，R 2为芳香环衍生物吸电子基团。
  2. 根据权利要求1所述的一种含四苯基苯的有机发光材料，其特征在于所述R 1为以下1～20取代基中的一种：
    Figure PCTCN2020070205-appb-100002
    其中，R＇为氢原子、叔丁基、甲氧基、氰基、氟原子或烷基链，n为0～10 的自然数，*为取代位置；
    所述R 2为以下a～o取代基中的一种：
    Figure PCTCN2020070205-appb-100003
    其中，R＇＇为氢原子、叔丁基、甲氧基、氰基、氟原子或烷基链，n为0～10的自然数，*为取代位置。
  3. 根据权利要求2所述的一种含四苯基苯的有机发光材料，其特征在于：所述烷基链指具有1～20个碳原子的直链、支链或者环状烷基链，或一个或多个碳原子被氧原子、烯基、炔基、芳基、羰基、羟基、氨基、羧基、氰基、硝基或者酯基取代的烷基链，或一个或多个氢原子被氟原子、氯原子、溴原子、碘原子取代的烷基链。
  4. 权利要求1～3任一项所述的一种含四苯基苯的有机发光材料的制备方法，其特征在于包含以下步骤：
    以1,4-二溴-2,5-三联苯和R 2取代的苯硼酸为原料，通过Suzuki反应得到含R 2的芳香环化合物；然后在四三苯基膦钯催化剂的作用下，含R 2的芳香环化合物与R 1取代的苯硼酸或硼酸酯进行反应，得到含四苯基苯的有机发光材料；上述制备方法的反应式如下式所示：
    Figure PCTCN2020070205-appb-100004
  5. 权利要求1～3任一项所述的一种含四苯基苯的有机发光材料在有机电致发光器件中的应用。
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