WO2020077831A1 - 电致发光材料、电致发光材料的制备方法及发光器件 - Google Patents

电致发光材料、电致发光材料的制备方法及发光器件 Download PDF

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WO2020077831A1
WO2020077831A1 PCT/CN2018/123169 CN2018123169W WO2020077831A1 WO 2020077831 A1 WO2020077831 A1 WO 2020077831A1 CN 2018123169 W CN2018123169 W CN 2018123169W WO 2020077831 A1 WO2020077831 A1 WO 2020077831A1
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electroluminescent material
reactant
preparing
molecular structure
layer
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罗佳佳
李先杰
顾宇
黄金昌
杨林
白亚梅
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武汉华星光电半导体显示技术有限公司
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    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present application relates to the field of display, and in particular to an electroluminescent material, a method for preparing an electroluminescent material, and a light-emitting device.
  • organic light emitting diodes (Organic Light Emitting Diode) have self-luminous properties, and the materials that dominate their light emission are mainly electroluminescent materials.
  • the short life span of current blue light-emitting electroluminescent materials often leads to The failure of light-emitting diodes, therefore, it is necessary to provide a long-life blue light-emitting electroluminescent material, a method of preparing the electroluminescent material, and a light-emitting device.
  • the present application provides an electroluminescent material, a method for preparing an electroluminescent material, and a light-emitting device, so as to realize an electroluminescent material that emits blue light with a long life, a method for preparing the electroluminescent material, and a light-emitting device.
  • An electroluminescent material, the molecular structure of the electroluminescent material is:
  • R is: or
  • the emission wavelength of the electroluminescent material is 425 nm-475 nm.
  • the molecular structure of the electroluminescent material is The molecular structural formula is The emission wavelength of the electroluminescent material is 425 nm-450 nm.
  • the molecular structure of the electroluminescent material is The molecular structural formula is The emission wavelength of the electroluminescent material is 430nm-460nm.
  • the molecular structure of the electroluminescent material is The molecular structural formula is The emission wavelength of the electroluminescent material is 450 nm-475 nm.
  • a preparation method of electroluminescent material includes:
  • the first reactant and the second reactant reacting to generate the electroluminescent material, wherein the molecular structure of the first reactant is Where R is The R ′ is Cl, Br or I, the second reactant is 9,10-dihydro-9,9-dideuterated methyl acridine, and the molecular structure of the second reactant is
  • the molar ratio of the first reactant and the second reactant is 1: 0.5-1: 2.
  • the first reactant and the second reactant are reacted in a solvent to generate the electroluminescent material
  • the solvent includes styrene, perchloroethylene, toluene, and three One or a combination of vinyl chloride, acetone, ethylene glycol ether and triethanolamine.
  • the solvent has additives, and the additives include potassium hydroxide, sodium hydroxide, sodium bicarbonate, [1,1'-bis (diphenylphosphino) di Ferrocene) Palladium dichloride (Pd (dppf) Cl 2 ), potassium acetate (KOAc), sodium acetate (NaOAc), potassium nitrate (KNO 3 ), palladium acetate (Pd (OAc) 2 ), magnesium sulfate (MgSO 4 ) And one or more combinations of sodium tert-butoxide (NaO t -Bu) and tri-tert-butylphosphine tetrafluoroborate.
  • the additives include potassium hydroxide, sodium hydroxide, sodium bicarbonate, [1,1'-bis (diphenylphosphino) di Ferrocene) Palladium dichloride (Pd (dppf) Cl 2 ), potassium acetate (KOAc), sodium acetate (NaOAc), potassium n
  • the reaction temperature at which the first reactant and the second reactant react to form the electroluminescent material is 100 degrees Celsius to 150 degrees Celsius.
  • the reaction time for the first reactant and the second reactant to generate the electroluminescent material is 12 hours to 64 hours.
  • the molecular structural formula of the electroluminescent material is:
  • R is: or
  • the providing of the first reactant and the second reactant, and the reaction of the first reactant and the second reactant to generate the electroluminescent material includes:
  • the first reactant and the second reactant react to form a mixture including the electroluminescent material
  • the mixture including the electroluminescent material is separated and purified to obtain the electroluminescent material.
  • the separation and purification of the mixture including the electroluminescent material to obtain the electroluminescent material includes:
  • the mixture including the electroluminescent material is chromatographed using a chromatography column.
  • the extraction solvent may be one or a combination of dichloromethane, chloroform, and tetrahydrofuran.
  • a light-emitting device including:
  • a substrate layer, the substrate layer includes a base substrate and a first electrode layer provided on the base substrate;
  • a hole transport and injection layer, the hole transport and injection layer is provided on the substrate layer and electrically connected to the first electrode layer;
  • a light-emitting layer, the light-emitting layer is provided on the hole transport and injection layer;
  • An electron transport layer provided on the light emitting layer
  • R is:
  • the molecular structure of the electroluminescent material is The molecular structural formula is The emission wavelength of the electroluminescent material is 425 nm-450 nm.
  • the molecular structure of the electroluminescent material is The molecular structural formula is The emission wavelength of the electroluminescent material is 430nm-460nm.
  • the molecular structure of the electroluminescent material is The molecular structural formula is The emission wavelength of the electroluminescent material is 450 nm-475 nm.
  • the electroluminescent material, the preparation method of the electroluminescent material, and the light-emitting device provided in the embodiments of the present application include: providing a first reactant and a second reactant, the first reactant and the second reactant reacting A mixture comprising the electroluminescent material, wherein the molecular structure of the first reactant is Where R is The R ′ is Cl, Br or I, the second reactant is 9,10-dihydro-9,9-dideuterated methyl acridine, and the molecular structure of the second reactant is Separately purifying the mixture including the electroluminescent material to obtain the electroluminescent material, thereby realizing a blue light-emitting electroluminescent material having a long lifetime, a method for preparing the electroluminescent material, and a light emitting device.
  • FIG. 1 is a photoluminescence spectrum diagram of an electroluminescent material in toluene provided by this application.
  • FIG. 2 is a schematic structural diagram of a light emitting device provided by this application.
  • FIG. 3 is a comparison diagram of the attenuation of the luminous efficiency with time of the light emitting device provided by the present application and the light emitting device in the prior art.
  • This application provides an electroluminescent material.
  • the molecular structure of the electroluminescent material is:
  • R is:
  • FIG. 1 is a photoluminescence spectrum chart of electroluminescent material in toluene provided by the present application.
  • the emission wavelength of the electroluminescent material is 425 nm-475 nm.
  • the light emitted by the electroluminescent material is blue.
  • the molecular structure of the electroluminescent material is The molecular structural formula is The emission wavelength of the electroluminescent material is 425 nm-450 nm.
  • the molecular structure of the electroluminescent material is The molecular structural formula is The emission wavelength of the electroluminescent material is 430nm-460nm.
  • the molecular structure of the electroluminescent material is The molecular structural formula is The emission wavelength of the electroluminescent material is 450 nm-475 nm.
  • Table 1 is the peak value of the fluorescence spectrum of the electroluminescent material and the energy level value of each energy state.
  • PL Peak is the peak value of the fluorescence spectrum of the electroluminescent material
  • S 1 is the lowest singlet energy level value
  • T 1 is the lowest triplet energy level value
  • ⁇ E ST S 1 -T 1
  • HOMO Is the energy level of the highest electron occupying orbit
  • LUMO is the energy level of the lowest electron not occupying the orbit.
  • the present application also provides a method for preparing an electroluminescent material.
  • the method includes:
  • the first reactant and the second reactant reacting to generate the electroluminescent material, wherein the molecular structure of the first reactant is Where R is The R ′ is Cl, Br or I, the second reactant is 9,10-dihydro-9,9-dideuterated methyl acridine, and the molecular structure of the second reactant is
  • the molar ratio of the first reactant to the second reactant is 1: 0.5-1: 2. In some embodiments, the molar ratio of the first reactant to the second reactant may be 1: 0.8, 1: 1, or 1: 1.5. In some embodiments, the ratio of the first reactant to the second reactant may be 10 millimoles of the first reactant corresponding to 9 millimoles of the second reactant and 2 moles of the first One reactant corresponds to 2.5 moles of the second reactant or 50 millimoles of the first reactant corresponds to 60 millimoles of the second reactant.
  • the first reactant and the second reactant are reacted in a solvent to generate the electroluminescent material.
  • the solvent includes one or a combination of styrene, perchloroethylene, toluene, trichloroethylene, acetone, ethylene glycol ether, and triethanolamine.
  • the solvent has additives, which include potassium hydroxide, sodium hydroxide, sodium bicarbonate, [1,1'-bis (diphenylphosphino) ferrocene] palladium dichloride (Pd (dppf) Cl 2 ), potassium acetate (KOAc), sodium acetate (NaOAc), potassium nitrate (KNO 3 ), palladium acetate (Pd (OAc) 2 ), magnesium sulfate (MgSO 4 ), sodium tert-butoxide (NaO t -Bu) And one or more of tri-tert-butylphosphine tetrafluoroborate.
  • additives include potassium hydroxide, sodium hydroxide, sodium bicarbonate, [1,1'-bis (diphenylphosphino) ferrocene] palladium dichloride (Pd (dppf) Cl 2 ), potassium acetate (KOAc), sodium acetate (NaOAc), potassium nitrate (KNO 3
  • the reaction temperature of the first reactant and the second reactant to generate the electroluminescent material is 100 degrees Celsius-150 degrees Celsius.
  • the reaction time between the first reactant and the second reactant to form the electroluminescent material is 12 hours to 64 hours.
  • the mixture comprising the electroluminescent material is separated and purified by using one or a combination of dichloromethane, chloroform and tetrahydrofuran to obtain the electroluminescent material.
  • reaction formula of the first reactant and the second reactant to generate the electroluminescent material is:
  • reaction formula of the first reactant and the second reactant to generate the electroluminescent material is:
  • reaction formula of the first reactant and the second reactant to generate the electroluminescent material is:
  • the extraction solvent may be one or a combination of dichloromethane, chloroform and tetrahydrofuran.
  • FIG. 2 is a schematic structural diagram of a light emitting device provided by this application.
  • the present application provides a light emitting device 10.
  • the light emitting device 10 includes a substrate layer 11, a hole transport and injection layer 12, a light emitting layer 13, an electron transport layer 14 and a second electrode layer 15.
  • the substrate layer 11 includes a base substrate 111 and a first electrode layer 112 provided on the base substrate 111.
  • the hole transport and injection layer 12 is provided on the substrate layer 10.
  • the hole transport and injection layer 12 is electrically connected to the first electrode layer 112.
  • the light-emitting layer 13 is disposed on the hole transport and injection layer 12.
  • the electron transport layer 14 is disposed on the light-emitting layer 13.
  • the second electrode layer 15 is electrically connected to the electron transport layer 14.
  • the base substrate 111 may be a glass substrate.
  • the first electrode layer 112 may use indium tin oxide.
  • the hole transport and injection layer 12 may be poly 3,4-ethylenedioxythiophene: polystyrene sulfonate (PEDOT: PSS).
  • the electron transport layer 14 may be 1,3,5-tris (3- (3-pyridyl) phenyl) benzene (Tm3PyPB).
  • the second electrode layer 15 may be lithium fluoride / aluminum (LiF / Al).
  • the light-emitting layer 13 includes the electroluminescent material, and the molecular structure of the electroluminescent material is:
  • FIG. 3 is a comparison chart of the attenuation of the luminous efficiency of the light-emitting device provided in this application with the light-emitting device in the prior art with time.
  • Table 2 is a performance data table of the light emitting device provided in this application and the light emitting device in the prior art.
  • the light-emitting device provided in this application and the light-emitting device in the prior art have the similar maximum current efficiency, the same color coordinate value, and the similar maximum external quantum efficiency.
  • the decay percentage of the luminous efficiency is less than 1%, and the decay percentage of the luminous efficiency of the light emitting device in the prior art at time t has reached 2%.
  • the electroluminescent material, the preparation method of the electroluminescent material, and the light-emitting device provided in the embodiments of the present application include: providing a first reactant and a second reactant, the first reactant and the second reactant reacting A mixture comprising the electroluminescent material, wherein the molecular structure of the first reactant is Where R is The R ′ is Cl, Br or I, the second reactant is 9,10-dihydro-9,9-dideuterated methyl acridine, and the molecular structure of the second reactant is Separately purifying the mixture including the electroluminescent material to obtain the electroluminescent material, thereby realizing a blue light-emitting electroluminescent material having a long lifetime, a method for preparing the electroluminescent material, and a light emitting device.

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Abstract

本申请实施方式所提供的电致发光材料、电致发光材料的制备方法及发光器件，所述方法包括：提供第一反应物和第二反应物，所述第一反应物和第二反应物进行反应生成包括所述电致发光材料的混合物，分离提纯所述包括所述电致发光材料的混合物，得到所述电致发光材料。

Description

电致发光材料、电致发光材料的制备方法及发光器件 技术领域
本申请涉及显示领域，具体涉及一种电致发光材料、电致发光材料的制备方法及发光器件。
背景技术
在现有技术中，有机发光二极管(Organic Light Emitting Diode)具有自发光特性，主导其发光的材料主要为电致发光材料，但是，当前的发出蓝光的电致发光材料的寿命短，往往导致有机发光二极管的失效，因此，有必要提供一种具有长寿命的、发出蓝光的电致发光材料、电致发光材料的制备方法及发光器件。
技术问题
本申请提供一种电致发光材料、电致发光材料的制备方法及发光器件，以实现具有长寿命的、发出蓝光的电致发光材料、电致发光材料的制备方法及发光器件。
技术解决方案
一种电致发光材料，所述电致发光材料的分子结构式为：
Figure PCTCN2018123169-appb-000001
其中，所述R为：
Figure PCTCN2018123169-appb-000002
或者
Figure PCTCN2018123169-appb-000003
在所述电致发光材料中，所述电致发光材料的发射波长为425纳米-475纳米。
在所述电致发光材料中，当所述R为
Figure PCTCN2018123169-appb-000004
时，所述电致发光材料的分子结构式为
Figure PCTCN2018123169-appb-000005
所述分子结构式为
Figure PCTCN2018123169-appb-000006
的所述电致发光材料的发射波长为425纳米-450纳米。
在所述电致发光材料中，当所述R为
Figure PCTCN2018123169-appb-000007
时，所述电致发光材料的分子结构式为
Figure PCTCN2018123169-appb-000008
所述分子结构式为
Figure PCTCN2018123169-appb-000009
的所述电致发光材料的发射波长为430纳米-460纳米。
在所述电致发光材料中，当所述R为
Figure PCTCN2018123169-appb-000010
时，所述电致发光材料的分子结构式为
Figure PCTCN2018123169-appb-000011
所述分子结构式为
Figure PCTCN2018123169-appb-000012
的所述电致发光材料的发射波长为450纳米-475纳米。
一种电致发光材料的制备方法，包括：
提供第一反应物和第二反应物，所述第一反应物和第二反应物进行反应生成所述电致发光材料，其中，所述第一反应物的分子结构式为
Figure PCTCN2018123169-appb-000013
其中，所述R为
Figure PCTCN2018123169-appb-000014
所述R’为Cl、Br或者I，所述第二反应物为9,10-二氢-9,9-二氘代甲基吖啶，所述第二反应物的分子结构式为
Figure PCTCN2018123169-appb-000015
在所述电致发光材料的制备方法中，所述第一反应物和第二反应物的摩尔比为：1:0.5-1:2。
在所述电致发光材料的制备方法中，所述第一反应物和第二反应物在溶剂中进行反应生成所述电致发光材料，所述溶剂包括苯乙烯、全氯乙烯、甲苯、三氯乙烯、丙酮、乙烯乙二醇醚和三乙醇胺中的一种或几种的组合。
在所述电致发光材料的制备方法中，所述溶剂中具有添加剂，所述添加剂包括氢氧化钾、氢氧化钠、碳酸氢钠、[1,1'-双(二苯基膦基)二茂铁]二氯化钯(Pd(dppf)Cl 2)、醋酸钾(KOAc)、醋酸钠(NaOAc)、硝酸钾(KNO 3)、醋酸钯(Pd(OAc) 2)、硫酸镁(MgSO 4)和叔丁醇钠(NaO t-Bu)和三叔丁基膦四氟硼酸盐中的一种或几种的组合。
在所述电致发光材料的制备方法中，所述第一反应物和第二反应物进行反应生成所述电致发光材料的反应温度为100摄氏度-150摄氏度。
在所述电致发光材料的制备方法中，所述第一反应物和第二反应物进行反应生成所述电致发光材料的反应时间为12小时-64小时。
在所述电致发光材料的制备方法中，所述电致发光材料的分子结构式为：
Figure PCTCN2018123169-appb-000016
其中，所述R为：
Figure PCTCN2018123169-appb-000017
或者
Figure PCTCN2018123169-appb-000018
在所述电致发光材料的制备方法中，所述提供第一反应物和第二反应物，所述第一反应物和第二反应物进行反应生成所述电致发光材料，包括：
提供第一反应物和第二反应物；
所述第一反应物和第二反应物进行反应，生成包括所述电致发光材料的混合物；
对包括所述电致发光材料的混合物进行分离提纯以得到所述电致发光材料。
在所述电致发光材料的制备方法中，所述对所述包括所述电致发光材料的混合物进行分离提纯以得到所述电致发光材料，包括：
采用萃取溶剂对包括所述电致发光材料的混合物进行萃取；
采用层析柱对包括所述电致发光材料的混合物进行层析。
在所述电致发光材料的制备方法中，所述萃取溶剂可以为二氯甲烷、三氯甲烷和四氢呋喃中的一种或几种的组合。
在所述电致发光材料的制备方法中，所述层析柱的配比可以为二氯甲烷的体积：正己烷的体积＝1:0.5-1:10。
一种发光器件，包括：
基板层，所述基板层包括衬底基板和设置于衬底基板上的第一电极层；
空穴传输和注入层，所述空穴传输和注入层设置于所述基板层上，并与所述 第一电极层电连接；
发光层，所述发光层设置于所述空穴传输和注入层上；
电子传输层，所述电子传输层设置于所述发光层上；以及
第二电极层，所述第二电极层电连接所述电子传输层，其中，所述发光层包括电致发光材料，所述电致发光材料的分子结构式为：
Figure PCTCN2018123169-appb-000019
其中，所述R为：
Figure PCTCN2018123169-appb-000020
在所述电致发光材料中，当所述R为
Figure PCTCN2018123169-appb-000021
时，所述电致发光材料的分子结构式为
Figure PCTCN2018123169-appb-000022
所述分子结构式为
Figure PCTCN2018123169-appb-000023
的所述电致发光材料的发射波长为425纳米-450纳米。
在所述电致发光材料中，当所述R为
Figure PCTCN2018123169-appb-000024
时，所述电致发光材料的分子结构式为
Figure PCTCN2018123169-appb-000025
所述分子结构式为
Figure PCTCN2018123169-appb-000026
的所述电致发光材料的发射波长为430纳米-460纳米。
在所述电致发光材料中，当所述R为
Figure PCTCN2018123169-appb-000027
时，所述电致发光材料的分子结构式为
Figure PCTCN2018123169-appb-000028
所述分子结构式为
Figure PCTCN2018123169-appb-000029
的所述电致发光材料的发射波长为450纳米-475纳米。
有益效果
本申请实施方式所提供的电致发光材料、电致发光材料的制备方法及发光器件，包括：提供第一反应物和第二反应物，所述第一反应物和第二反应物进行反应生成包括所述电致发光材料的混合物，其中，所述第一反应物的分子结构式为
Figure PCTCN2018123169-appb-000030
其中，所述R为
Figure PCTCN2018123169-appb-000031
所述R’为Cl、Br或者I，所述第二反应物为9,10-二氢-9,9-二氘代甲基吖啶，所述第二反应物的分子结构式为
Figure PCTCN2018123169-appb-000032
分离提纯所述包括所述电致发光材料的混合物，得到所述电致发光材料，从而实现了具有长寿命的、发出蓝光的电致发光材料、电致发光材料的制备方法及发光器件。
附图说明
为了更清楚地说明本申请实施例中的技术方案，下面将对实施例描述中所需要使用的附图作简单地介绍，显而易见地，下面描述中的附图仅仅是本申请的一些实施例，对于本领域技术人员来讲，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为本申请所提供的电致发光材料在甲苯中的光致发光光谱图。
图2为本申请所提供的发光器件的结构示意图。
图3为本申请所提供的发光器件与现有技术中的发光器件的发光效率随时间的衰减对比图。
本发明的实施方式
本申请提供一种电致发光材料，所述电致发光材料的分子结构式为：
Figure PCTCN2018123169-appb-000033
其中，所述R为：
Figure PCTCN2018123169-appb-000034
请参阅图1，图1为本申请所提供的电致发光材料在甲苯中的光致发光光谱图。所述电致发光材料的发射波长为425纳米-475纳米。所述电致发光材料发出的光线为蓝色。
在一种实施方式中，当所述R为
Figure PCTCN2018123169-appb-000035
时，所述电致发光材料的分子结构式为
Figure PCTCN2018123169-appb-000036
所述分子结构式为
Figure PCTCN2018123169-appb-000037
的所述电致发光材料的发射波长为425纳米-450纳米。
在一种实施方式中，当所述R为
Figure PCTCN2018123169-appb-000038
时，所述电致发光材料的分子结构式 为
Figure PCTCN2018123169-appb-000039
所述分子结构式为
Figure PCTCN2018123169-appb-000040
的所述电致发光材料的发射波长为430纳米-460纳米。
在一种实施方式中，当所述R为
Figure PCTCN2018123169-appb-000041
时，所述电致发光材料的分子结构式为
Figure PCTCN2018123169-appb-000042
所述分子结构式为
Figure PCTCN2018123169-appb-000043
的所述电致发光材料的发射波长为450纳米-475纳米。
请参阅表1，表1为所述电致发光材料的荧光光谱的波峰值及各个能态的能级值。
Figure PCTCN2018123169-appb-000044
Figure PCTCN2018123169-appb-000045
表1
其中，PL Peak为所述电致发光材料的荧光光谱的波峰值，S 1为最低单重态能级值、T 1为最低三重态能级值，△E ST＝S 1-T 1，HOMO为最高电子占据轨道的能级值，LUMO为最低电子未占据轨道的能级值。
本申请还提供一种电致发光材料的制备方法。所述方法包括：
提供第一反应物和第二反应物，所述第一反应物和第二反应物进行反应生成所述电致发光材料，其中，所述第一反应物的分子结构式为
Figure PCTCN2018123169-appb-000046
其中，所述R为
Figure PCTCN2018123169-appb-000047
所述R’为Cl、Br或者I，所述第二反应物为9,10-二氢-9,9-二氘代甲基吖啶，所述第二反应物的分子结构式为
Figure PCTCN2018123169-appb-000048
在一种实施方式中，所述第一反应物和第二反应物的摩尔比为：1:0.5-1:2。在一些实施方式中，所述第一反应物和第二反应物的摩尔比可以为：1:0.8、1:1或者1:1.5等。在一些实施方式中，所述第一反应物和第二反应物的配比可以为10毫摩的所述第一反应物对应9毫摩的所述第二反应物、2摩尔的所述第一反应物对应2.5摩尔的所述第二反应物或者50毫摩的所述第一反应物对应60毫摩的所述第二反应物。
在一种实施方式中，所述第一反应物和第二反应物在溶剂中进行反应生成所述电致发光材料。所述溶剂包括苯乙烯、全氯乙烯、甲苯、三氯乙烯、丙酮、乙烯乙二醇醚和三乙醇胺中的一种或几种的组合。所述溶剂中具有添加剂，所述添加剂包括氢氧化钾、氢氧化钠、碳酸氢钠、[1,1'-双(二苯基膦基)二茂铁]二氯化钯(Pd(dppf)Cl 2)、醋酸钾(KOAc)、醋酸钠(NaOAc)、硝酸钾(KNO 3)、醋酸钯(Pd(OAc) 2)、硫酸镁(MgSO 4)、叔丁醇钠(NaO t-Bu)和三叔丁基膦四氟硼酸盐中的一种或几种的组合。
在一种实施方式中，所述第一反应物和第二反应物进行反应生成所述电致发光材料的反应温度为100摄氏度-150摄氏度。所述第一反应物和第二反应物进行反应生成所述电致发光材料的反应时间为12小时-64小时。采用二氯甲烷、三氯甲烷和四氢呋喃中的一种或几种的组合对所述包括所述电致发光材料的混合物进行分离提纯以得到所述电致发光材料。
在一种实施方式中，当所述R为
Figure PCTCN2018123169-appb-000049
所述R’为Br时，所述第一反应物 的分子结构式为
Figure PCTCN2018123169-appb-000050
所述第一反应物和所述第二反应物进行反应生成所述电致发光材料的反应式为：
Figure PCTCN2018123169-appb-000051
在一种实施方式中，向200mL二口瓶中加入10毫摩的
Figure PCTCN2018123169-appb-000052
15毫摩的9,10-二氢-9,9-二氘代甲基吖啶，0.2毫摩的醋酸钯和1毫摩的三叔丁基膦四氟硼酸盐，然后在手套箱中加入15毫摩叔丁醇钠(NaO t-Bu)，在氩气氛围下打入40mL的甲苯，在110摄氏度反应30小时得到混合物，分离提纯所述混合物，得到所述电致发光材料
Figure PCTCN2018123169-appb-000053
在一种实施方式中，当所述R为
Figure PCTCN2018123169-appb-000054
所述R’为Br时，所述第一反应物的分子结构式为
Figure PCTCN2018123169-appb-000055
所述第一反应物和所述第二反应物进行反应生成所述电致发光材料的反应式为：
Figure PCTCN2018123169-appb-000056
在一种实施方式中，向200mL二口瓶中加入5毫摩的
Figure PCTCN2018123169-appb-000057
4毫摩的9,10-二氢-9,9-二氘代甲基吖啶，0.4毫摩的醋酸钯和1毫摩的三叔丁基膦四氟硼酸盐，然后在手套箱中加入15毫摩叔丁醇钠(NaO t-Bu)，在氩气氛围下打入40mL的甲苯，在120摄氏度反应36小时得到混合物，分离提纯所述混合物，得到所述电致发光材料
Figure PCTCN2018123169-appb-000058
在一种实施方式中，当所述R为
Figure PCTCN2018123169-appb-000059
所述R’为Br时，所述第一反应物的分子结构式为
Figure PCTCN2018123169-appb-000060
所述第一反应物和所述第二反应物进行反应生成所述电致发光材料的反应式为：
Figure PCTCN2018123169-appb-000061
在一种实施方式中，向100mL二口瓶中加入3毫摩的
Figure PCTCN2018123169-appb-000062
4毫摩的9,10-二氢-9,9-二氘代甲基吖啶，0.1毫摩的醋酸钯和0.5毫摩的三叔丁基膦四氟硼酸盐，然后在手套箱中加入10毫摩叔丁醇钠(NaO t-Bu)，在氩气氛围下打入40mL的甲苯，在110摄氏度反应48小时得到混合物，分离提纯所述混合物， 得到所述电致发光材料
Figure PCTCN2018123169-appb-000063
在分离提纯中，可以先将反应液冷却至室温，将反应液倒入冰水中，采用萃取溶剂萃取2次-5次，合并有机相，旋成硅胶，采用层析柱进行层析，得蓝白色粉末，也即所述电致发光材料。所述电致发光材料的产率大于等于55％。
所述萃取溶剂可以为二氯甲烷、三氯甲烷和四氢呋喃中的一种或几种的组合。所述层析柱的配比可以为二氯甲烷的体积：正己烷的体积＝1:0.5-1:10。
请参阅图2，图2为本申请所提供的发光器件的结构示意图。
本申请提供一种发光器件10。所述发光器件10包括基板层11、空穴传输和注入层12、发光层13、电子传输层14和第二电极层15。
所述基板层11包括衬底基板111和设置于衬底基板111上的第一电极层112。所述空穴传输和注入层12设置于所述基板层10上。所述空穴传输和注入层12与所述第一电极层112电连接。所述发光层13设置于所述空穴传输和注入层12上。所述电子传输层14设置于所述发光层13上。所述第二电极层15电连接所述电子传输层14。
所述衬底基板111可以为玻璃基板。所述第一电极层112可以采用氧化铟锡。所述空穴传输和注入层12可以为聚3，4-乙撑二氧噻吩：聚苯乙烯磺酸盐(PEDOT:PSS)。所述电子传输层14可以为1,3,5-三(3-(3-吡啶基)苯基)苯(Tm3PyPB)。所述第二电极层15可以为氟化锂/铝(LiF/Al)。所述发光层13包括所述电致发光材料，所述电致发光材料的分子结构式为：
Figure PCTCN2018123169-appb-000064
请参阅图3，为本申请所提供的发光器件与现有技术中的发光器件的发光效率随时间的衰减对比图。请参阅表2，表2为本申请所提供的发光器件与现有技术中的发光器件的性能数据表。
Figure PCTCN2018123169-appb-000065
Figure PCTCN2018123169-appb-000066
本申请所提供的发光器件和现有技术中的发光器件在相似的最高电流效率、相同的色坐标值、相似的最大外量子效率的情况下，本申请所提供的发光器件在时间为t时的发光效率的衰减百分比小于1％，而现有技术中的发光器件在时间为t时的发光效率的衰减百分比已经达到2％。
本申请实施方式所提供的电致发光材料、电致发光材料的制备方法及发光器件，包括：提供第一反应物和第二反应物，所述第一反应物和第二反应物进行反应生成包括所述电致发光材料的混合物，其中，所述第一反应物的分子结构式为
Figure PCTCN2018123169-appb-000067
其中，所述R为
Figure PCTCN2018123169-appb-000068
所述R’为Cl、Br或者I，所述第二反应物为9,10-二氢-9,9-二氘代甲基吖啶，所述第二反应物的分子结构式为
Figure PCTCN2018123169-appb-000069
分离提纯所述包括所述电致发光材料的混合物，得到所述电致发光材料，从而实现了具有长寿命的、发出蓝光的电致发光材料、电致发光材料的制备方法及发光器件。
以上对本申请实施方式提供了详细介绍，本文中应用了具体个例对本申请的原理及实施方式进行了阐述，以上实施方式的说明只是用于帮助理解本申请。同时，对于本领域的技术人员，依据本申请的思想，在具体实施方式及应用范围上均会有改变之处，综上所述，本说明书内容不应理解为对本申请的限制。

Claims (20)

  1. 一种电致发光材料，其中，所述电致发光材料的分子结构式为：
    Figure PCTCN2018123169-appb-100001
    其中，所述R为：
    Figure PCTCN2018123169-appb-100002
    或者
    Figure PCTCN2018123169-appb-100003
  2. 如权利要求1所述的电致发光材料，其中，所述电致发光材料的发射波长为425纳米-475纳米。
  3. 如权利要求2所述的电致发光材料，其中，当所述R为
    Figure PCTCN2018123169-appb-100004
    时，所述电致发光材料的分子结构式为
    Figure PCTCN2018123169-appb-100005
    所述分子结构式为
    Figure PCTCN2018123169-appb-100006
    的所述电致发光材料的发射波长为425纳米-450纳米。
  4. 如权利要求2所述的电致发光材料，其中，当所述R为
    Figure PCTCN2018123169-appb-100007
    时，所述电致发光材料的分子结构式为
    Figure PCTCN2018123169-appb-100008
    所述分子结构式为
    Figure PCTCN2018123169-appb-100009
    的所述电致发光材料的发射波长为430纳米-460纳米。
  5. 如权利要求2所述的电致发光材料，其中，当所述R为
    Figure PCTCN2018123169-appb-100010
    时，所述电致发光材料的分子结构式为
    Figure PCTCN2018123169-appb-100011
    所述分子结构式为
    Figure PCTCN2018123169-appb-100012
    的所述电致发光材料的发射波长为450纳米-475纳米。
  6. 一种电致发光材料的制备方法，其中，包括：
    提供第一反应物和第二反应物，所述第一反应物和第二反应物进行反应生成所述电致发光材料，其中，所述第一反应物的分子结构式为
    Figure PCTCN2018123169-appb-100013
    其中，所述R为
    Figure PCTCN2018123169-appb-100014
    或者
    Figure PCTCN2018123169-appb-100015
    所述R’为Cl、Br或者I所述第二反应物为9,10-二氢-9,9-二氘代甲基吖啶，所述第二反应物的分子结构式为
    Figure PCTCN2018123169-appb-100016
  7. 如权利要求6所述电致发光材料的制备方法，其中，所述第一反应物和第二反应物的摩尔比为：1:0.5-1:2。
  8. 如权利要求6所述电致发光材料的制备方法，其中，所述第一反应物和第二反应物在溶剂中进行反应生成所述电致发光材料，所述溶剂包括苯乙烯、全氯乙烯、甲苯、三氯乙烯、丙酮、乙烯乙二醇醚和三乙醇胺中的一种或几种的组合。
  9. 如权利要求6所述电致发光材料的制备方法，其中，所述溶剂中具有添加剂，所述添加剂包括氢氧化钾、氢氧化钠、碳酸氢钠、[1,1'-双(二苯基膦基)二茂铁]二氯化钯(Pd(dppf)Cl 2)、醋酸钾(KOAc)、醋酸钠(NaOAc)、硝酸钾(KNO 3)、醋酸钯(Pd(OAc) 2)、硫酸镁(MgSO 4)和叔丁醇钠(NaO t-Bu)和三叔丁基膦四氟硼酸盐中的一种或几种的组合。
  10. 如权利要求6所述的电致发光材料的制备方法，其中，所述第一反应物和第二反应物进行反应生成所述电致发光材料的反应温度为100摄氏度-150摄氏度。
  11. 如权利要求6所述的电致发光材料的制备方法，其中，所述第一反应物和第二反应物进行反应生成所述电致发光材料的反应时间为12小时-64小时。
  12. 如权利要求6所述的电致发光材料的制备方法，其中，所述电致发光材料的分子结构式为：
    Figure PCTCN2018123169-appb-100017
    其中，所述R为：
    Figure PCTCN2018123169-appb-100018
    或者
    Figure PCTCN2018123169-appb-100019
  13. 如权利要求6所述的电致发光材料的制备方法，其中，所述提供第一反应物和第二反应物，所述第一反应物和第二反应物进行反应生成所述电致发光材料，包括：
    提供第一反应物和第二反应物；
    所述第一反应物和第二反应物进行反应，生成包括所述电致发光材料的混合物；
    对包括所述电致发光材料的混合物进行分离提纯以得到所述电致发光材料。
  14. 如权利要求13所述的电致发光材料的制备方法，其中，所述对所述包括所述电致发光材料的混合物进行分离提纯以得到所述电致发光材料，包括：
    采用萃取溶剂对包括所述电致发光材料的混合物进行萃取；
    采用层析柱对包括所述电致发光材料的混合物进行层析。
  15. 如权利要求14所述的电致发光材料的制备方法，其中，所述萃取溶剂可以为二氯甲烷、三氯甲烷和四氢呋喃中的一种或几种的组合。
  16. 如权利要求14所述的电致发光材料的制备方法，其中，所述层析柱的配比可以为二氯甲烷的体积：正己烷的体积＝1:0.5-1:10。
  17. 一种发光器件，其中，包括：
    基板层，所述基板层包括衬底基板和设置于衬底基板上的第一电极层；
    空穴传输和注入层，所述空穴传输和注入层设置于所述基板层上，并与所述第一电极层电连接；
    发光层，所述发光层设置于所述空穴传输和注入层上；
    电子传输层，所述电子传输层设置于所述发光层上；以及
    第二电极层，所述第二电极层电连接所述电子传输层，其中，所述发光层包括电致发光材料，所述电致发光材料的分子结构式为：
    Figure PCTCN2018123169-appb-100020
    其中，所述R为：
    Figure PCTCN2018123169-appb-100021
    或者
    Figure PCTCN2018123169-appb-100022
  18. 如权利要求17所述的发光器件，其中，当所述R为
    Figure PCTCN2018123169-appb-100023
    时，所述电致发光材料的分子结构式为
    Figure PCTCN2018123169-appb-100024
    所述分子结构式为
    Figure PCTCN2018123169-appb-100025
    的所述电致发光材料的发射波长为425纳米-450纳米。
  19. 如权利要求17所述的发光器件，其中，当所述R为
    Figure PCTCN2018123169-appb-100026
    时，所述电致发光材料的分子结构式为
    Figure PCTCN2018123169-appb-100027
    所述分子结构式为
    Figure PCTCN2018123169-appb-100028
    的所述电致发光材料的发射波长为430纳米-460纳米。
  20. 如权利要求17所述的发光器件，其中，当所述R为
    Figure PCTCN2018123169-appb-100029
    时，所述电致发光材料的分子结构式为
    Figure PCTCN2018123169-appb-100030
    所述分子结构式为
    Figure PCTCN2018123169-appb-100031
    的所述电致发光材料的发射波长为450纳米-475纳米。
PCT/CN2018/123169 2018-10-17 2018-12-24 电致发光材料、电致发光材料的制备方法及发光器件 WO2020077831A1 (zh)

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