WO2018014387A1 - 发光材料及其制备方法与使用该发光材料的有机发光二极管 - Google Patents

发光材料及其制备方法与使用该发光材料的有机发光二极管 Download PDF

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WO2018014387A1
WO2018014387A1 PCT/CN2016/094778 CN2016094778W WO2018014387A1 WO 2018014387 A1 WO2018014387 A1 WO 2018014387A1 CN 2016094778 W CN2016094778 W CN 2016094778W WO 2018014387 A1 WO2018014387 A1 WO 2018014387A1
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formula
light
luminescent material
emitting material
organic light
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李先杰
吴元均
苏仕健
李云川
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深圳市华星光电技术有限公司
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    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to the field of display technologies, and in particular, to a luminescent material, a method for fabricating the same, and an organic light emitting diode using the luminescent material.
  • OLED organic light-emitting diode
  • OLED organic electroluminescent display
  • the working temperature has wide adaptability, light volume, fast response, easy to realize color display and large screen display, easy to realize integration with integrated circuit driver, easy to realize flexible display, and the like, and thus has broad application prospects.
  • OLED displays use organic light-emitting diodes for illumination, so it is extremely important to improve the efficiency and lifetime of organic light-emitting diodes.
  • organic light-emitting diodes have made great progress.
  • fluorescent phosphorescence hybridization white light devices with simple structure and high efficiency can be obtained.
  • the efficiency of such fluorescent phosphor hybrid devices is largely dependent on the efficiency of the fluorescence, so the development of efficient fluorescent materials remains of great importance.
  • luminescent small molecules can be obtained in commercial applications because of their simple preparation steps, stable structure, and purification, so that higher device efficiencies can be obtained.
  • the use of small molecules for evaporation or solution processing to prepare multilayer devices has received great attention and has made great progress.
  • the efficiency of the device is greatly limited because it usually only uses 25% of singlet excitons.
  • the Japanese Adachi team used the thermal activation delayed fluorescence mechanism to make the exciton utilization rate of all organic materials reach 100%, which made the device efficiency of organic fluorescence leap.
  • due to the scarcity of such materials expanding the types of such materials is of great significance for future application choices.
  • organic small molecule luminescent materials with simple structure and good performance and satisfying commercialization requirements are still very limited, and luminescent materials with low development cost and excellent efficiency are still of great significance.
  • the object of the present invention is to provide a luminescent material which has a single structure, a certain molecular weight, a good solubility and a film forming property, and can be applied to a small molecule organic light emitting diode.
  • the object of the present invention is also to provide a method for preparing a luminescent material, which has simple steps and a yield. high.
  • Another object of the present invention is to provide an organic light emitting diode, wherein the light emitting layer contains the above light emitting material, and has high luminous efficiency and stability.
  • the present invention first provides a luminescent material having a structural formula of Wherein Ar 1 and Ar 2 are each selected from the group consisting of aromatic amino groups represented by formula (1), formula (2), formula (3), formula (4), formula (5), formula (6), and formula (7). ;
  • Ar 1 is the same as Ar 2 .
  • the luminescent material comprises one or more of the following compounds:
  • the invention also provides a preparation method of a luminescent material, comprising the following steps:
  • Step 2 intermediate A luminescent material is obtained by reacting with an aromatic amine compound through a Ullmann reaction or Suzuki, the structural formula of the luminescent material being Wherein Ar 1 and Ar 2 are each selected from the group consisting of aromatic amino groups represented by formula (1), formula (2), formula (3), formula (4), formula (5), formula (6), and formula (7). ;
  • Ar 1 is the same as Ar 2 .
  • the luminescent material comprises one or more of the following compounds:
  • the step 1 includes:
  • Step 12 First hydrolyzed under alkaline conditions and then acidified to obtain
  • the present invention provides an organic light emitting diode comprising a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode stacked in this order from bottom to top on the substrate;
  • the luminescent layer includes a luminescent material, and the luminescent material has a structural formula of
  • Ar 1 and Ar 2 are each selected from the group consisting of aromatic amino groups represented by formula (1), formula (2), formula (3), formula (4), formula (5), formula (6), and formula (7). ;
  • Ar 1 is the same as Ar 2 .
  • the luminescent material comprises one or more of the following compounds:
  • the invention has the beneficial effects that the luminescent material provided by the invention has a single structure, a certain molecular weight, good solubility and film forming property, and stable film morphology; and has a high decomposition temperature and a relatively low sublimation temperature. It is easy to sublimate into a high-purity luminescent material, which can be applied to a small molecule organic light-emitting diode; by changing the linked aromatic amine group, the physical properties can be further improved, and the performance of the photovoltaic device based on the luminescent material can be improved.
  • the invention provides a method for preparing a luminescent material, which comprises using m-bromophenol and 2-fluoro-4-bromobenzonitrile as starting materials, and obtaining an intermediate of a luminescent material through a series of simple reactions, and finally passing the Ullmann reaction. Or Suzuki reaction to obtain a luminescent material, the steps are simple, and the yield is high.
  • the invention provides an organic light emitting diode, wherein the light emitting layer comprises the above light emitting material, and has high luminous efficiency and stability.
  • FIG. 1 is a flow chart of a method for preparing a luminescent material of the present invention
  • FIG. 2 is a schematic structural view of an organic light emitting diode of the present invention.
  • the invention firstly provides a luminescent material having the structural formula Wherein Ar 1 and Ar 2 are each selected from the group consisting of aromatic amino groups represented by formula (1), formula (2), formula (3), formula (4), formula (5), formula (6), and formula (7). ;
  • Ar 1 is the same as Ar 2 .
  • the luminescent material comprises one or more of the following compounds:
  • the luminescent material has the advantages of single structure, determined molecular weight, good solubility and film forming property, and stable film morphology; high decomposition temperature and relatively low sublimation temperature, and easy sublimation into high-purity luminescent materials, applicable For small molecule organic light-emitting diodes; by changing the attached aromatic amine groups, the physical properties can be further improved, and the performance of the photovoltaic device based on the luminescent material can be improved.
  • the present invention also provides a method for preparing the above luminescent material, comprising the following steps:
  • the step 1 includes:
  • step 11 The specific implementation steps of the step 11 are:
  • Step 12 Hydrolyzed under alkaline conditions and acidified to obtain a compound (a2).
  • step 12 The specific implementation steps of the step 12 are:
  • step 13 The specific implementation steps of the step 13 are:
  • Step 2 intermediate A luminescent material is obtained by a Ullmann reaction or Suzuki with an aromatic amine compound, and the luminescent material has a structural formula of Wherein Ar 1 and Ar 2 are each selected from the group consisting of aromatic amino groups represented by formula (1), formula (2), formula (3), formula (4), formula (5), formula (6), and formula (7). ;
  • Ar 1 is the same as Ar 2 .
  • the luminescent material comprises one or more of the following compounds:
  • the aromatic amine compound comprises carbazole, diphenylamine, 9,9-dimethyl acridine, p-carbazole boronate, p-phenyloxazolium borate, p-three.
  • Example 4 Intermediate It is obtained by reacting with p-phenyloxazole borate through Suzuki The reaction formula is as follows:
  • Example 5 Intermediate Obtained by reacting with triphenylamine borate through Suzuki The reaction formula is as follows:
  • Example 6 Intermediate It is obtained by reacting with p-phenylphenothiazine-S,S-dioxaborate through Suzuki.
  • the reaction formula is as follows:
  • the preparation method of the above luminescent material uses m-bromophenol and 2-fluoro-4-bromobenzonitrile as starting materials to obtain an intermediate of a luminescent material through a series of simple reactions, and finally obtains luminescence by a Ullmann reaction or a Suzuki reaction.
  • the material has simple steps and high yield.
  • the present invention further provides an organic light emitting diode comprising the above luminescent material, comprising a substrate 10, an anode 20, a hole injection layer 30, and a hole transport layer 40 stacked in this order from bottom to top on the substrate 10. , the light-emitting layer 50, the electron transport layer 60, the electron injection layer 70, and the cathode 80;
  • the luminescent layer 50 includes a luminescent material, and the luminescent material has a structural formula of
  • Ar 1 and Ar 2 are each selected from the group consisting of aromatic amino groups represented by formula (1), formula (2), formula (3), formula (4), formula (5), formula (6), and formula (7). ;
  • Ar 1 is the same as Ar 2 .
  • the luminescent material comprises one or more of the following compounds:
  • the mass percentage of the light-emitting material is 1%.
  • the light emitting layer 50 may emit red light, yellow light, green light, or blue light.
  • the material of the anode 20 includes a transparent metal oxide, and the transparent metal oxide is preferably indium tin oxide (ITO).
  • ITO indium tin oxide
  • the material of the hole injection layer 30 includes 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HAT-CN)
  • HAT-CN 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene
  • the material of the hole transport layer 40 includes 1,1-bis[(di-4-tolylamino)phenyl]cyclohexane (TAPC), the 1,1-bis[(di-4) -tolylamino)phenyl]cyclohexane has the structural formula
  • the light emitting layer 50 further includes 4,4′-bis(N-carbazole)-1,1′-biphenyl (CBP), and the 4,4′-bis(N-carbazole)-1 , the structural formula of 1'-biphenyl is
  • the material of the electron transport layer 60 includes 1,3,5-tris[(3-pyridyl)-3-phenyl]benzene (TmPyPB), the 1,3,5-tri[(3- The structural formula of pyridyl)-3-phenyl]benzene is
  • the material of the electron injection layer 70 includes lithium fluoride (LiF).
  • the material of the cathode 80 includes aluminum (Al).
  • the anode 20 has a thickness of 95 nm
  • the hole injection layer 30 has a thickness of 5 nm
  • the hole transport layer 40 has a thickness of 20 nm
  • the light-emitting layer 50 has a thickness of 35 nm
  • the electron transport The thickness of the layer 60 is 55 nm
  • the thickness of the electron injecting layer 70 is 1 nm
  • the thickness of the cathode 80 is greater than 80 nm.
  • the preparation process of the organic light emitting diode is as follows: the indium tin oxide transparent conductive glass is ultrasonically treated in a cleaning agent, and then washed with deionized water, degreased by ultrasonic in a mixed solvent of acetone/ethanol, and then in a clean environment.
  • the luminescent material provided by the invention has a single structure, a certain molecular weight, good solubility and film forming property, and stable film morphology; high decomposition temperature and relatively low sublimation temperature, and easy Sublimation into a high-purity luminescent material, which can be applied to a small molecule organic light-emitting diode; by changing the attached aromatic amine group, the physical properties can be further improved, and the performance of the photovoltaic device based on the luminescent material can be improved.
  • the invention provides a method for preparing a luminescent material, which comprises using m-bromophenol and 2-fluoro-4-bromobenzonitrile as starting materials, and obtaining an intermediate of a luminescent material through a series of simple reactions, and finally passing the Ullmann reaction. Or Suzuki reaction to obtain a luminescent material, the steps are simple, and the yield is high.
  • the invention provides an organic light emitting diode, wherein the light emitting layer comprises the above light emitting material, and has high luminous efficiency and stability.

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Abstract

一种结构通式为（I）的发光材料及其制备方法与使用该发光材料的有机发光二极管，其中，Ar1、Ar2分别选自式(1)、式(2)、式(3)、式(4)、式(5)、式(6)、式(7)所示的芳香氨基团。该发光材料结构单一，分子量确定，具有较好的溶解性及成膜性，且薄膜形态稳定；具有很高的分解温度和比较低的升华温度，容易升华成高纯度的发光材料，可应用于小分子有机发光二极管。所述发光材料的制备方法，以间溴苯酚与2-氟-4-溴苄腈为起始原料，通过一系列的简单反应得到发光材料的中间体，最后通过乌尔曼反应或铃木反应得到发光材料，步骤简单，产率高。所述有机发光二极管，发光层含有上述发光材料，具有较高的发光率与稳定性。

Description

发光材料及其制备方法与使用该发光材料的有机发光二极管 技术领域
本发明涉及显示技术领域，尤其涉及一种发光材料及其制备方法与使用该发光材料的有机发光二极管。
背景技术
有机发光二极管(OLED，Organic Light-Emitting Diode)显示器，也称为有机电致发光显示器，是一种新兴的平板显示装置，由于其具有制备工艺简单、成本低、功耗低、发光亮度高、工作温度适应范围广、体积轻薄、响应速度快，而且易于实现彩色显示和大屏幕显示、易于实现和集成电路驱动器相匹配、易于实现柔性显示等优点，因而具有广阔的应用前景。
OLED显示器利用有机发光二极管进行发光，因此改善有机发光二极管的效率和寿命显得极为重要。至今，有机发光二极管已经取得了长足的进展，通过荧光磷光杂化，可以获得器件结构简单且效率很高的白光器件。而这种荧光磷光杂化器件的效率很大程度上依赖于荧光的效率，因此发展高效的荧光材料依然具有举足轻重的意义。
相比于聚合物而言，发光小分子由于制备步骤简便，结构稳定，能够纯化，因而可以获得更高的器件效率，从而可得到商业化应用。利用小分子进行蒸镀或者溶液加工，制备多层器件的方法已经受到了极大关注，并且取得了巨大的进展。但是基于传统的有机荧光材料由于通常只能利用25％的单线态激子，因此器件的效率受到极大的限制。而近期，由日本人Adachi课题组利用热活化延迟荧光机理，使全有机材料的激子利用率也可以达到100％，使得有机荧光的器件效率实现了飞跃。然而由于这类材料种类稀少，因而拓展这类材料的种类对未来的应用选择具有很重要的意义。至今为止，结构简单、且兼具良好性能、满足商业化需求的有机小分子发光材料依旧十分有限，开发成本低廉且效率优异的发光材料依然具有举足轻重的意义。
发明内容
本发明的目的在于提供一种发光材料，结构单一，分子量确定，具有较好的溶解性及成膜性，可应用于小分子有机发光二极管。
本发明的目的还在于提供一种发光材料的制备方法，步骤简单，产率 高。
本发明的目的还在于提供一种有机发光二极管，发光层含有上述发光材料，具有较高的发光效率与稳定性。
为实现上述目的，本发明首先提供一种发光材料，结构通式为
Figure PCTCN2016094778-appb-000001
其中，Ar1、Ar2分别选自式(1)、式(2)、式(3)、式(4)、式(5)、式(6)、式(7)所示的芳香氨基团；
Figure PCTCN2016094778-appb-000002
Ar1与Ar2相同。
所述发光材料包括以下化合物中的一种或多种：
Figure PCTCN2016094778-appb-000003
Figure PCTCN2016094778-appb-000004
本发明还提供一种发光材料的制备方法，包括如下步骤：
步骤1、制备中间体
Figure PCTCN2016094778-appb-000005
步骤2、中间体
Figure PCTCN2016094778-appb-000006
与芳香胺化合物通过乌尔曼反应或铃木得到发光材料，所述发光材料的结构通式为
Figure PCTCN2016094778-appb-000007
其中，Ar1、Ar2分别选自式(1)、式(2)、式(3)、式(4)、式(5)、式(6)、式(7)所示的芳香氨基团；
Figure PCTCN2016094778-appb-000008
Ar1与Ar2相同。
所述发光材料包括以下化合物中的一种或多种：
Figure PCTCN2016094778-appb-000009
Figure PCTCN2016094778-appb-000010
所述步骤1包括：
步骤11、间溴苯酚与2-氟-4-溴苄腈反应得到
Figure PCTCN2016094778-appb-000011
步骤12、
Figure PCTCN2016094778-appb-000012
先在碱性条件下水解，再酸化，得到
Figure PCTCN2016094778-appb-000013
步骤13、
Figure PCTCN2016094778-appb-000014
发生脱水缩合反应，得到
Figure PCTCN2016094778-appb-000015
和中间体
Figure PCTCN2016094778-appb-000016
本发明提供一种有机发光二极管，包括基板、在基板上从下到上依次层叠设置的阳极、空穴注入层、空穴传输层、发光层、电子传输层、电子注入层、及阴极；
所述发光层包括发光材料，所述发光材料的结构通式为
Figure PCTCN2016094778-appb-000017
其中，Ar1、Ar2分别选自式(1)、式(2)、式(3)、式(4)、式(5)、式(6)、式(7)所示的芳香氨基团；
Figure PCTCN2016094778-appb-000018
Ar1与Ar2相同。
所述发光材料包括以下化合物中的一种或多种：
Figure PCTCN2016094778-appb-000019
Figure PCTCN2016094778-appb-000020
本发明的有益效果：本发明提供的一种发光材料，结构单一，分子量确定，具有较好的溶解性及成膜性，且薄膜形态稳定；具有很高的分解温度和比较低的升华温度，容易升华成高纯度的发光材料，可应用于小分子有机发光二极管；通过改变连接的芳香胺基团，可进一步改善其物理特性，提升基于该发光材料的光电器件的性能。本发明提供的一种发光材料的制备方法，以间溴苯酚与2-氟-4-溴苄腈为起始原料，通过一系列的简单反应得到发光材料的中间体，最后通过乌尔曼反应或铃木反应得到发光材料，步骤简单，产率高。本发明提供的一种有机发光二极管，发光层含有上述发光材料，具有较高的发光效率与稳定性。
为了能更进一步了解本发明的特征以及技术内容，请参阅以下有关本发明的详细说明与附图，然而附图仅提供参考与说明用，并非用来对本发明加以限制。
附图说明
下面结合附图，通过对本发明的具体实施方式详细描述，将使本发明的技术方案及其它有益效果显而易见。
附图中，
图1为本发明的发光材料的制备方法的流程图；
图2为本发明的有机发光二极管的结构示意图。
具体实施方式
为更进一步阐述本发明所采取的技术手段及其效果，以下结合本发明的优选实施例及其附图进行详细描述。
本发明首先提供一种发光材料，其结构通式为
Figure PCTCN2016094778-appb-000021
其中，Ar1、Ar2分别选自式(1)、式(2)、式(3)、式(4)、式(5)、式 (6)、式(7)所示的芳香氨基团；
Figure PCTCN2016094778-appb-000022
优选的，Ar1与Ar2相同。
具体的，所述发光材料包括以下化合物中的一种或多种：
Figure PCTCN2016094778-appb-000023
Figure PCTCN2016094778-appb-000024
上述发光材料，结构单一，分子量确定，具有较好的溶解性及成膜性，且薄膜形态稳定；具有很高的分解温度和比较低的升华温度，容易升华成高纯度的发光材料，可应用于小分子有机发光二极管；通过改变连接的芳香胺基团，可进一步改善其物理特性，提升基于该发光材料的光电器件的性能。
请参阅图1，本发明还提供一种上述发光材料的制备方法，包括如下步骤：
步骤1、制备中间体
Figure PCTCN2016094778-appb-000025
所述中间体
Figure PCTCN2016094778-appb-000026
的合成路线为：
Figure PCTCN2016094778-appb-000027
具体的，所述步骤1包括：
步骤11、间溴苯酚与2-氟-4-溴苄腈反应得到
Figure PCTCN2016094778-appb-000028
(a1)。
所述步骤11的具体实施步骤为：
于250ml三口烧瓶中将0.73g(30mmol)NaH缓慢加入到溶解有4.6g(25mmol)间溴苯酚的20ml干燥二甲基甲酰胺(DMF)中,然后向其中滴加溶解有5g(25mmol)2-氟-4-溴苄腈的20ml干燥二甲基甲酰胺中。在氮气保护下，加热回流反应20h，反应结束后降至室温，将反应液倒入50ml1M 的NaOH溶液中，二氯甲烷(DCM)萃取，减压出掉溶剂，过硅胶柱，得到白色固体5.0g，即为化合物a1。分子式：C13H7Br2NO，MS：350.89，元素分析：C,44.23；H,2.00；Br,45.27；N,3.97；O,4.53。
步骤12、
Figure PCTCN2016094778-appb-000029
先在碱性条件下水解，再酸化，得到化合物
Figure PCTCN2016094778-appb-000030
(a2)。
所述步骤12的具体实施步骤为：
于250ml三口烧瓶中加入80ml去离子水、15g KOH、及80ml乙醇，将5.2g化合物a1加入到反应瓶中，氮气保护下回流过夜。反应完冷却至室温，将反应液加入到100ml 6M的盐酸中，冰浴析出白色固体抽滤，干燥得到白色固体5.1g，即为化合物a2。分子式：C13H8Br2O3，MS：369.88，元素分析：C,41.97；H,2.17；Br,42.96；O,12.90。
步骤13、
Figure PCTCN2016094778-appb-000031
发生脱水缩合反应，得到
Figure PCTCN2016094778-appb-000032
和中间体
Figure PCTCN2016094778-appb-000033
所述步骤13的具体实施步骤为：
在500ml单口烧瓶中加入2.75g(10mmol)化合物a2，加入500ml氯仿作为溶剂，滴加3.2g(20mmol，2equ)三氟乙酸酐，室温搅拌10min，加冰浴冷却10min，然后加入0.5g三氟化硼乙醚，去掉冰浴室温反应12h。反应完，加亚硫酸钠饱和水溶液，淬灭多余的三氟乙酸酐，分液，减压蒸馏除掉溶剂，过柱分别得到
Figure PCTCN2016094778-appb-000034
和中间体
Figure PCTCN2016094778-appb-000035
产率分别为42％和53％。中间体
Figure PCTCN2016094778-appb-000036
的分子式：C13H6Br2O2， MS：351.87，元素分析：C,44.11；H,1.71；Br,45.14；O,9.04。
步骤2、中间体
Figure PCTCN2016094778-appb-000037
与芳香胺化合物通过乌尔曼反应或铃木(Suzuki)得到发光材料，所述发光材料的结构通式为
Figure PCTCN2016094778-appb-000038
其中，Ar1、Ar2分别选自式(1)、式(2)、式(3)、式(4)、式(5)、式(6)、式(7)所示的芳香氨基团；
Figure PCTCN2016094778-appb-000039
优选的，Ar1与Ar2相同。
具体的，所述发光材料包括以下化合物中的一种或多种：
Figure PCTCN2016094778-appb-000040
Figure PCTCN2016094778-appb-000041
具体的，所述步骤2中，所述芳香胺化合物包括咔唑、二苯胺、9,9-二甲基吖啶、对咔唑苯硼酸酯、对苯基咔唑硼酸酯、对三苯胺硼酸酯、及对苯基吩噻嗪-S,S-二氧硼酸酯中的一种或多种；
所述咔唑的结构式为
Figure PCTCN2016094778-appb-000042
所述二苯胺的结构式为
Figure PCTCN2016094778-appb-000043
所述9,9-二甲基吖啶的结构式为
Figure PCTCN2016094778-appb-000044
所述对咔唑苯硼酸酯的结构式为
Figure PCTCN2016094778-appb-000045
所述对苯基咔唑硼酸酯的结构式为
Figure PCTCN2016094778-appb-000046
所述对三苯胺硼酸酯的结构式为
Figure PCTCN2016094778-appb-000047
所述对苯基吩噻嗪-S,S-二氧硼酸酯的结构式为
Figure PCTCN2016094778-appb-000048
以下结合具体实施例，详细说明所述步骤2的具体实施方法。
实施例1：中间体
Figure PCTCN2016094778-appb-000049
与咔唑通过乌尔曼反应得到
Figure PCTCN2016094778-appb-000050
反应式如下：
Figure PCTCN2016094778-appb-000051
具体实施步骤为：
在氮气保护下，向三口烧瓶中加入100ml甲苯、0.72g(2mmol)中间 体
Figure PCTCN2016094778-appb-000052
0.67g(4mmol)咔唑，在搅拌下加入0.3g叔丁基醇钠，再加入20mg三(二亚苄基丙酮)二钯(Pd2(dba)3)，再加入0.3ml 10％三叔丁基膦正己烷溶液，加热回流，反应过夜。降温，用二氯甲烷萃取有机相，旋干，过柱。得白色固体产物0.68g，产率65％。分子式：C37H22N2O2；M/Z＝526.17；理论值：526.17(100.0％),527.17(41.1％),528.17(8.5％),529.18(1.2％)；元素分析：C,84.39；H,4.21；N,5.32；O,6.08。
实施例2：中间体
Figure PCTCN2016094778-appb-000053
与二苯胺通过乌尔曼反应得到
Figure PCTCN2016094778-appb-000054
反应式如下：
Figure PCTCN2016094778-appb-000055
具体实施步骤为：
在氮气保护下，向三口烧瓶中加入100ml甲苯、0.72g(2mmol)中间体
Figure PCTCN2016094778-appb-000056
0.84g(4mmol)二苯胺，在搅拌下加入0.3g叔丁基醇钠，再加入20mg三(二亚苄基丙酮)二钯(Pd2(dba)3)，再加入0.3ml 10％三叔丁基膦正己烷溶液，加热回流，反应过夜。降温，用二氯甲烷萃取有机相，旋干，过柱。得白色固体产物0.59g，产率56％。分子式：C37H26N2O2；M/Z＝530.20；理论值：530.20(100.0％),531.20(40.8％),532.21(7.9％),533.21(1.2％)；元素分析：C,83.75；H,4.94；N,5.28；O,6.03。
实施例3：中间体
Figure PCTCN2016094778-appb-000057
与对咔唑苯硼酸酯通过铃木反应得到
Figure PCTCN2016094778-appb-000058
反应式如下：
Figure PCTCN2016094778-appb-000059
具体实施步骤为：
在氮气气氛下，往250ml烧瓶中加入96ml甲苯、32ml乙醇、16ml 2M的碳酸钾水溶液、0.72g(2mmol)中间体
Figure PCTCN2016094778-appb-000060
2.06g(1.2equ)对咔唑苯硼酸酯，室温搅拌，然后加入100mg三苯基磷钯(催化剂)，96℃回流24小时。冷却至室温，二氯甲烷萃取，无水硫酸镁干燥。得白色固体产物1.17g，产率86％。分子式：C49H30N2O2；M/Z＝678.23；理论值：678.23(100.0％),679.23(53.8％),680.24(14.0％),681.24(2.6％)；元素分析：C,86.70；H,4.45；N,4.13；O,4.71。
实施例4：中间体
Figure PCTCN2016094778-appb-000061
与对苯基咔唑硼酸酯通过铃木反应得到
Figure PCTCN2016094778-appb-000062
反应式如下：
Figure PCTCN2016094778-appb-000063
具体实施步骤为：
在氮气气氛下，往250ml烧瓶中加入96ml甲苯、32ml乙醇、16ml 2M的碳酸钾水溶液、0.72g(2mmol)中间体
Figure PCTCN2016094778-appb-000064
2.32g(1.2equ)对苯基咔唑硼酸酯，室温搅拌，然后加入100mg三苯基磷钯(催化剂)，96℃回流24小时。冷却至室温，二氯甲烷萃取，无水硫酸镁干燥。分离得白色固体1.20g，产率88％。分子式：C49H30N2O2；M/Z＝678.23；理论值：678.23(100.0％),679.23(53.8％),680.24(14.0％),681.24(2.6％)；元素分析：C,86.70；H,4.45；N,4.13；O,4.71。
实施例5：中间体
Figure PCTCN2016094778-appb-000065
与对三苯胺硼酸酯通过铃木反应得到
Figure PCTCN2016094778-appb-000066
反应式如下：
Figure PCTCN2016094778-appb-000067
具体实施步骤为：
在氮气气氛下，往250ml烧瓶中加入96ml甲苯、32ml乙醇、16ml 2M的碳酸钾水溶液、0.72g(2mmol)中间体
Figure PCTCN2016094778-appb-000068
2.32g(1.2equ)对三苯胺硼酸酯，室温搅拌，然后加入100mg三苯基磷钯(催化剂)，96℃回流24小时。冷却至室温，二氯甲烷萃取，无水硫酸镁干燥。得白色固体产物1.17g，产率86％。分子式：C49H34N2O2；M/Z＝682.26；理论值：686.26(100.0％),683.27(53.5％),684.27(14.4％),685.27(2.7％)；元素分析：C,86.19；H,5.02；N,4.10；O,4.69。
实施例6：中间体
Figure PCTCN2016094778-appb-000069
与对苯基吩噻嗪-S,S-二氧硼酸酯通过铃木反应得到
Figure PCTCN2016094778-appb-000070
反应式如下：
Figure PCTCN2016094778-appb-000071
具体实施步骤为：
在氮气气氛下，往250ml烧瓶中加入96ml甲苯、32ml乙醇、16ml 2M的碳酸钾水溶液、0.72g(2mmol)中间体
Figure PCTCN2016094778-appb-000072
2.06g(1.2equ)对苯基吩噻嗪-S,S-二氧硼酸酯，室温搅拌，然后加入100mg三苯基磷钯(催化剂)，96℃回流24小时。冷却至室温，二氯甲烷萃取，无水硫酸镁干燥。 得白色固体产物1.39g，产率86％。分子式：C49H30N2O6S2；M/Z＝806.15；理论值：806.15(100.0％),807.16(53.6％),808.16(16.2％),808.15(9.4％),809.15(5.0％),809.16(3.4％),807.15(2.3％),810.16(1.4％)；元素分析：C,72.94；H,3.75；N,3.47；O,11.90；S,7.95。
上述发光材料的制备方法，以间溴苯酚与2-氟-4-溴苄腈为起始原料，通过一系列的简单反应得到发光材料的中间体，最后通过乌尔曼反应或铃木反应得到发光材料，步骤简单，产率高。
请参阅图2，本发明还提供一种含有上述发光材料的有机发光二极管，包括基板10、在基板10上从下到上依次层叠设置的阳极20、空穴注入层30、空穴传输层40、发光层50、电子传输层60、电子注入层70、及阴极80；
所述发光层50包括发光材料，所述发光材料的结构通式为
Figure PCTCN2016094778-appb-000073
其中，Ar1、Ar2分别选自式(1)、式(2)、式(3)、式(4)、式(5)、式(6)、式(7)所示的芳香氨基团；
Figure PCTCN2016094778-appb-000074
优选的，Ar1与Ar2相同。
具体的，所述发光材料包括以下化合物中的一种或多种：
Figure PCTCN2016094778-appb-000075
Figure PCTCN2016094778-appb-000076
优选的，所述发光层50的材料中，所述发光材料的质量百分比为1％。
具体的，所述发光层50可以发红光、黄光、绿光、或者蓝光。
具体的，所述阳极20的材料包括透明金属氧化物，所述透明金属氧化物优选为氧化铟锡(ITO)。
具体的，所述空穴注入层30的材料包括2,3,6,7,10,11-六氰基-1,4,5,8,9,12-六氮杂三亚苯(HAT-CN)，所述2,3,6,7,10,11-六氰基 -1,4,5,8,9,12-六氮杂三亚苯的结构式为
Figure PCTCN2016094778-appb-000077
具体的，所述空穴传输层40的材料包括1,1-双[(二-4-甲苯基氨基)苯基]环己烷(TAPC)，所述1,1-双[(二-4-甲苯基氨基)苯基]环己烷的结构式为
Figure PCTCN2016094778-appb-000078
具体的，所述发光层50还包括4,4'-双(N-咔唑)-1,1'-联苯(CBP)，所述4,4'-双(N-咔唑)-1,1'-联苯的结构式为
Figure PCTCN2016094778-appb-000079
具体的，所述电子传输层60的材料包括1,3,5-三[(3-吡啶基)-3-苯基]苯(TmPyPB)，所述1,3,5-三[(3-吡啶基)-3-苯基]苯的结构式为
Figure PCTCN2016094778-appb-000080
具体的，所述电子注入层70的材料包括氟化锂(LiF)。
具体的，所述阴极80的材料包括铝(Al)。
优选的，所述阳极20的厚度为95nm，所述空穴注入层30的厚度为5nm，所述空穴传输层40的厚度为20nm，所述发光层50的厚度为35nm，所述电子传输层60的厚度为55nm，所述电子注入层70的厚度为1nm，所述阴极80的厚度大于80nm。
所述有机发光二极管的制备过程如下：将氧化铟锡透明导电玻璃在清洗剂中进行超声处理，再用去离子水清洗，在丙酮/乙醇的混合溶剂中利用 超声除油，之后在洁净的环境下烘烤至完全除去水分，然后用紫外光和臭氧进行清洗，并用低能阳离子轰击得到阳极20，将带有阳极20的透明导电玻璃置于真空腔内，抽真空至1×10-5～9×10-3Pa，然后在所述阳极20上依次蒸镀空穴注入层30、空穴传输层40、数层发光层50、电子传输层60、电子注入层70与阴极80，最终得到本实施例的有机发光二极管。
综上所述，本发明提供的一种发光材料，结构单一，分子量确定，具有较好的溶解性及成膜性，且薄膜形态稳定；具有很高的分解温度和比较低的升华温度，容易升华成高纯度的发光材料，可应用于小分子有机发光二极管；通过改变连接的芳香胺基团，可进一步改善其物理特性，提升基于该发光材料的光电器件的性能。本发明提供的一种发光材料的制备方法，以间溴苯酚与2-氟-4-溴苄腈为起始原料，通过一系列的简单反应得到发光材料的中间体，最后通过乌尔曼反应或铃木反应得到发光材料，步骤简单，产率高。本发明提供的一种有机发光二极管，发光层含有上述发光材料，具有较高的发光效率与稳定性。
以上所述，对于本领域的普通技术人员来说，可以根据本发明的技术方案和技术构思作出其他各种相应的改变和变形，而所有这些改变和变形都应属于本发明权利要求的保护范围。

Claims (10)

  1. 一种发光材料，结构通式为
    Figure PCTCN2016094778-appb-100001
    其中，Ar1、Ar2分别选自式(1)、式(2)、式(3)、式(4)、式(5)、式(6)、式(7)所示的芳香氨基团；
    Figure PCTCN2016094778-appb-100002
  2. 如权利要求1所述的发光材料，其中，Ar1与Ar2相同。
  3. 如权利要求2所述的发光材料，包括以下化合物中的一种或多种：
    Figure PCTCN2016094778-appb-100003
    Figure PCTCN2016094778-appb-100004
  4. 一种发光材料的制备方法，包括如下步骤：
    步骤1、制备中间体
    Figure PCTCN2016094778-appb-100005
    步骤2、中间体
    Figure PCTCN2016094778-appb-100006
    与芳香胺化合物通过乌尔曼反应或铃木得到发光材料，所述发光材料的结构通式为
    Figure PCTCN2016094778-appb-100007
    其中，Ar1、Ar2分别选自式(1)、式(2)、式(3)、式(4)、式(5)、式(6)、式(7)所示的芳香氨基团；
    Figure PCTCN2016094778-appb-100008
  5. 如权利要求4所述的发光材料的制备方法，其中，Ar1与Ar2相同。
  6. 如权利要求5所述的发光材料的制备方法，其中，所述发光材料包括以下化合物中的一种或多种：
    Figure PCTCN2016094778-appb-100009
    Figure PCTCN2016094778-appb-100010
  7. 如权利要求4所述的发光材料的制备方法，其中，所述步骤1包括：
    步骤11、间溴苯酚与2-氟-4-溴苄腈反应得到
    Figure PCTCN2016094778-appb-100011
    步骤12、
    Figure PCTCN2016094778-appb-100012
    先在碱性条件下水解，再酸化，得到
    Figure PCTCN2016094778-appb-100013
    步骤13、
    Figure PCTCN2016094778-appb-100014
    发生脱水缩合反应，得到
    Figure PCTCN2016094778-appb-100015
    和中间体
    Figure PCTCN2016094778-appb-100016
  8. 一种有机发光二极管，包括基板、在基板上从下到上依次层叠设置的阳极、空穴注入层、空穴传输层、发光层、电子传输层、电子注入层、及阴极；
    所述发光层包括发光材料，所述发光材料的结构通式为
    Figure PCTCN2016094778-appb-100017
    其中，Ar1、Ar2分别选自式(1)、式(2)、式(3)、式(4)、式(5)、式(6)、式(7)所示的芳香氨基团；
    Figure PCTCN2016094778-appb-100018
  9. 如权利要求8所述的有机发光二极管，其中，Ar1与Ar2相同。
  10. 如权利要求9所述的有机发光二极管，其中，所述发光材料包括以下化合物中的一种或多种：
    Figure PCTCN2016094778-appb-100019
    Figure PCTCN2016094778-appb-100020
PCT/CN2016/094778 2016-07-20 2016-08-12 发光材料及其制备方法与使用该发光材料的有机发光二极管 WO2018014387A1 (zh)

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