WO2020220474A1 - 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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WO2020220474A1
WO2020220474A1 PCT/CN2019/095411 CN2019095411W WO2020220474A1 WO 2020220474 A1 WO2020220474 A1 WO 2020220474A1 CN 2019095411 W CN2019095411 W CN 2019095411W WO 2020220474 A1 WO2020220474 A1 WO 2020220474A1
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reactant
electroluminescent material
intermediate product
material according
preparing
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汪亚民
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Wuhan China Star Optoelectronics Semiconductor Display Technology Co Ltd
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Wuhan China Star Optoelectronics Semiconductor Display Technology Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
    • C07F9/5325—Aromatic phosphine oxides or thioxides (P-C aromatic linkage)
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
    • C07F9/5329—Polyphosphine oxides or thioxides
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent materials, e.g. electroluminescent or chemiluminescent
    • C09K11/06—Luminescent materials, e.g. electroluminescent or chemiluminescent containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/1011—Condensed systems
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    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/10—Deposition of organic active material
    • H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
    • H10K71/15—Deposition of organic active material using liquid deposition, e.g. spin coating characterised by the solvent used
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/40—Thermal treatment, e.g. annealing in the presence of a solvent vapour

Definitions

  • This application relates to the field of display, in particular to an electroluminescent material, a preparation method of the electroluminescent material, and a light-emitting device.
  • Organic Light Emitting Diode (Organic Light Emitting Diode) has self-luminous characteristics, and the materials that dominate its luminescence are mainly electroluminescent materials.
  • the low luminous efficiency of current electroluminescent materials often leads to organic light emitting diodes. Therefore, it is necessary to provide an electroluminescent material with high luminous efficiency, a preparation method of the electroluminescent material, and a light emitting device.
  • This application provides an electroluminescent material with high electroluminescence efficiency, a preparation method of the electroluminescent material, and a light-emitting device.
  • This application proposes an electroluminescent material, the structural formula of the electroluminescent material is One of them.
  • This application also proposes a preparation method of electroluminescent material, including:
  • a first reactant and a second reactant are provided.
  • the first reactant and the second reactant react in the first reaction solution to form a first intermediate product, and the structural formula of the first reactant is One of the structural formula of the second reactant is
  • the structural formula of the first intermediate product is One of
  • a third reactant is provided, and the third reactant and the first intermediate product react under the action of an oxidizing agent to generate the electroluminescent material, wherein the structural formula of the third reactant is The structural formula of the electroluminescent material is One of them.
  • the first reactant and the second reactant are provided, and the first reactant and the second reactant react in the first reaction solution to form a first intermediate product
  • the steps include:
  • the first mixture including the first intermediate product is separated and purified and then dissolved in a first solvent to obtain a second mixture including the first intermediate product.
  • the third reactant and the first intermediate product react under the action of an oxidizing agent to form the electroluminescent material
  • the solution including the catalyst is slowly added to the second mixture, and then the third reactant is added dropwise, keeping the reaction temperature lower than the second temperature, stirring and reacting.
  • the first temperature is -10 degrees Celsius to -150 degrees Celsius.
  • the first temperature is -30 degrees Celsius to 100 degrees Celsius.
  • the second temperature is 60 degrees Celsius.
  • the third reactant and the first intermediate product react under the action of an oxidizing agent to form the electroluminescent material
  • the third reactant whose molar amount of the third reactant and the molar amount of the first intermediate product are 2 millimoles-20 millimoles corresponds to 1 millimole-10 millimoles of the first intermediate product.
  • the corresponding relationship between the volume of the first solvent and the molar amount of the first intermediate product is 10 milliliters-300 milliliters of the first solvent corresponding to 1 millimole-10 milliliters.
  • the first intermediate product ofixie is 10 milliliters-300 milliliters of the first solvent corresponding to 1 millimole-10 milliliters.
  • the first solvent is tetrahydrofuran.
  • the first reaction solution includes water.
  • the solution including the catalyst is a solution including the catalyst n-BuLi.
  • This application also proposes a light emitting device, including:
  • a substrate substrate layer the substrate layer includes a substrate and an anode layer, the anode layer is disposed on the substrate;
  • a hole injection layer, the hole injection layer is disposed on the anode layer;
  • a hole transport layer, the hole transport layer is disposed on the hole injection layer;
  • a light-emitting layer, the light-emitting layer is disposed on the hole transport layer;
  • An electron injection layer, the electron transport layer is disposed on the light-emitting layer
  • a cathode layer, the cathode layer is disposed on the electron injection layer;
  • the light-emitting layer includes the electroluminescent material, and the structural formula of the electroluminescent material is One of them.
  • This application provides an electroluminescent material, a preparation method of the electroluminescent material, and a light-emitting device.
  • an anthracene group and a triphenylphosphine oxide group By selecting an anthracene group and a triphenylphosphine oxide group, a molecule including an anthracene group has excellent luminescence characteristics and is Two electron-deficient triphenylphosphine oxide groups are attached to the 6 and 13 positions of the group. The non-coplanar conformation effectively prevents the filling of close molecules in the solid state, the formation of excimer molecules, and the quenching of fluorescence.
  • Figure 1 is the electroluminescent material provided by this application Electroluminescence spectra in solution state and film state.
  • FIG. 2 is a schematic diagram of the structure of the light emitting device provided by this application.
  • the electroluminescent material is an electroluminescent material capable of emitting blue light.
  • the application also provides a method for preparing the electroluminescent material.
  • the preparation method of the electroluminescent material includes:
  • A. Provide a first reactant and a second reactant.
  • the first reactant and the second reactant react in the first reaction solution to form a first intermediate product, and the structural formula of the first reactant is One of the structural formula of the second reactant is The structural formula of the first intermediate product is One of them.
  • the step of providing the first reactant and the second reactant, the first reactant and the second reactant reacting in the first reaction solution to form the first intermediate product may include:
  • a first reactant and a second reactant are provided, and the first reactant and the second reactant react in the first reaction solution to form a first mixture including a first intermediate product;
  • the first mixture is separated and purified and then dissolved in a first solvent to obtain a second mixture including the first intermediate product.
  • Water may be included in the first reaction solution.
  • the corresponding relationship between the volume of the first solvent and the molar amount of the first intermediate product is that 10 milliliters to 300 milliliters of the first solvent corresponds to 1 millimoles to 10 millimoles of the first intermediate product.
  • the corresponding relationship between the volume of the first solvent and the molar amount of the first intermediate product may be that 50 milliliters of the first solvent corresponds to 3 millimoles of the first intermediate product.
  • the corresponding relationship between the volume of the first solvent and the molar amount of the first intermediate product may also be that 200 milliliters of the first solvent corresponds to 8 millimoles of the first intermediate product.
  • reaction formula of the first reactant and the second reactant in the first reaction solution to generate the first intermediate product may be:
  • the third reactant and the first intermediate product react under the action of an oxidizing agent to generate the electroluminescent material, wherein the structural formula of the third reactant is The structural formula of the electroluminescent material is One of them.
  • the catalyst In the step of providing the third reactant, the third reactant and the first intermediate product react under the action of an oxidizing agent to form the electroluminescent material, at the first temperature, the catalyst The solution is slowly added to the second mixture, and then the third reactant is added dropwise, keeping the reaction temperature lower than the second temperature, stirring and reacting.
  • the first temperature is -10 degrees Celsius to -150 degrees Celsius.
  • the second temperature is 60 degrees Celsius.
  • the third reactant whose molar amount of the third reactant and the molar amount of the first intermediate product are 2 millimoles-20 millimoles corresponds to 1 millimole-10 millimoles of the first intermediate product.
  • the reaction mixture was first quenched with deionized water, and then extracted with ethyl acetate to obtain the organic phase, then the organic phase was dried using MgSO 4 and concentrated under reduced pressure, and the residue was dissolved in CH 2 Cl 2 and add the oxidant solution. After stirring for 1 hour at room temperature, the organic phase is collected, and the organic phase is again dried with MgSO 4 and concentrated under reduced pressure.
  • the electroluminescent material is obtained by separation and purification by column chromatography.
  • Figure 1 is the electroluminescent material provided by this application Electroluminescence spectra in solution state and film state.
  • the electroluminescent material The maximum emission peak in the solution is located at 456nm, the electroluminescent material The maximum emission peak in the film state is located at 479nm.
  • the electroluminescent material is a blue luminescent material.
  • FIG. 2 provides a light emitting device 100 for this application.
  • the light emitting device 100 includes a base substrate layer 11, a hole injection layer 12, a hole transport layer 13, a light emitting layer 14, an electron injection layer 15 and a cathode layer 16.
  • the base substrate layer 11 includes a substrate 111 and an anode layer 112.
  • the substrate 111 may be a glass substrate or a transparent plastic substrate.
  • the anode layer 112 is disposed on the substrate 111.
  • the anode layer 112 may be indium tin oxide material.
  • the hole injection layer 12 is disposed on the anode layer 112.
  • the hole transport layer 13 is disposed on the hole injection layer 12.
  • the light-emitting layer 14 is disposed on the hole transport layer 13.
  • the light-emitting layer 14 includes the electroluminescent material, and the structural formula of the electroluminescent material is One of them.
  • the electron injection layer 15 is disposed on the light-emitting layer 14.
  • the cathode layer 16 is disposed on the electron injection layer 15.
  • the cathode layer 16 may be a lithium fluoride/aluminum material.
  • This application provides an electroluminescent material, a preparation method of the electroluminescent material, and a light-emitting device.
  • an anthracene group and a triphenylphosphine oxide group By selecting an anthracene group and a triphenylphosphine oxide group, a molecule including an anthracene group has excellent luminescence characteristics and is Two electron-deficient triphenylphosphine oxide groups are attached to the 6 and 13 positions of the group. The non-coplanar conformation effectively prevents the filling of close molecules in the solid state, the formation of excimer molecules, and the quenching of fluorescence.

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Abstract

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，通过选用蒽基团和三苯基氧化膦基团，利用包括蒽基团的分子具有优异的发光特性和在蒽基团的6位和13位附加两个缺电子的三苯基氧化膦基团，实现了一种能发出蓝光的、发光效率高的电致发光材料、电致发光材料的制备方法及发光器件。

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，当前的电致发光材料的发光效率低，往往导致有机发光二极管的失效，因此，有必要提供一种发光效率高的电致发光材料、电致发光材料的制备方法及发光器件。
技术问题
本申请提供一种具有电致发光效率高的电致发光材料、电致发光材料的制备方法及发光器件。
技术解决方案
本申请提出一种电致发光材料，所述电致发光材料的结构式为
Figure PCTCN2019095411-appb-000001
Figure PCTCN2019095411-appb-000002
中的一种。
本申请还提出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在第一反应溶液中进行反应生成第一中间产物，所述第一反应物的结构式为
Figure PCTCN2019095411-appb-000003
Figure PCTCN2019095411-appb-000004
中的一种，所述第二反应物的结构式为
Figure PCTCN2019095411-appb-000005
所述第一中间产物的结构式为
Figure PCTCN2019095411-appb-000006
Figure PCTCN2019095411-appb-000007
中的一种；
提供第三反应物，所述第三反应物和所述第一中间产物在氧化剂的作用下进行反应生成所述电致发光材料，其中，所述第三反应物的结构式为
Figure PCTCN2019095411-appb-000008
所述电致发光材料的结构式为
Figure PCTCN2019095411-appb-000009
Figure PCTCN2019095411-appb-000010
中的一种。
在所述的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在第一反应溶液中进行反应生成第一中间产物的步骤包括：
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在第一反应溶液中进行反应生成包括第一中间产物的第一混合物；
对所述包括第一中间产物的第一混合物进行分离提纯后溶解于第一溶剂得到包括所述第一中间产物的第二混合物。
在所述的电致发光材料的制备方法中，在所述提供第三反应物，所述第三反应物和所述第一中间产物在氧化剂的作用下进行反应生成所述电致发光材料的步骤中，在第一温度下，将包括催化剂的溶液缓慢加入到所述第二混合物中，然后逐滴加入第三反应物，保持反应温度低于第二温度，搅拌并进行反应。
在所述的电致发光材料的制备方法中，所述第一温度为-10摄氏度至-150摄氏度。
在所述的电致发光材料的制备方法中，所述第一温度为-30摄氏度-100摄氏度。
在所述的电致发光材料的制备方法中，所述第二温度为60摄氏度。
在所述的电致发光材料的制备方法中，在所述提供第三反应物，所述第三反应物和所述第一中间产物在氧化剂的作用下进行反应生成所述电致发光材料中，所述第三反应物的摩尔量和所述第一中间产物的摩尔量为2毫摩-20毫摩的第三反应物对应1毫摩-10毫摩的第一中间产物。
在所述的电致发光材料的制备方法中，所述第一溶剂的体积与所述第一中间产物的摩尔量的对应关系为10毫升-300毫升的第一溶剂对应1毫摩-10毫摩的第一中间产物。
在所述的电致发光材料的制备方法中，所述第一溶剂为四氢呋喃。
在所述的电致发光材料的制备方法中，所述第一反应溶液中包括水。
在所述的电致发光材料的制备方法中，所述包括催化剂的溶液为包括催化剂n-BuLi的溶液。
本申请还提出一种发光器件，包括：
衬底基板层，所述衬底层包括基板和阳极层，所述阳极层设置于所述基板上；
空穴注入层，所述空穴注入层设置于所述阳极层上；
空穴传输层，所述空穴传输层设置于所述空穴注入层上；
发光层，所述发光层设置于所述空穴传输层上；
电子注入层，所述电子传输层设置于所述发光层上；
阴极层，所述阴极层设置于所述电子注入层上；
所述发光层包括所述电致发光材料，所述电致发光材料的结构式为
Figure PCTCN2019095411-appb-000011
Figure PCTCN2019095411-appb-000012
中的一种。
有益效果
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，通过选用蒽基团和三苯基氧化膦基团，利用包括蒽基团的分子具有优异的发光特性和在蒽基团的6位和13位附加两个缺电子的三苯基氧化膦基团，其非共面构象有效地阻止了密切分子在固态下的填充、准分子形成和荧光猝灭，实现了一种能发出蓝光的、发光效率高的电致发光材料、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中的技术方案，下面将对实施方式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方式，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为本申请提供的所述电致发光材料
Figure PCTCN2019095411-appb-000013
在溶液状态和薄膜状态下的电致发光光谱图。
图2为本申请所提供的发光器件的结构示意图。
本发明的实施方式
下面将结合本申请实施方式中的附图，对本申请中的技术方案进行清楚、完整地描述。显然，所描述的实施方式仅仅是本申请一部分实施方式，而不是全部的实施方式。基于本申请中的实施方式，本领域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方式，都属于本申请保护的范围。
本申请提供一种电致发光材料，所述电致发光材料的结构式为
Figure PCTCN2019095411-appb-000014
Figure PCTCN2019095411-appb-000015
中的一种。所述电致发光材料为能发出蓝光的电致发光材料。
本申请还提供一种电致发光材料的制备方法。所述电致发光材料的制备方法包括：
A、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在第一反应溶液中进行反应生成第 一中间产物，所述第一反应物的结构式为
Figure PCTCN2019095411-appb-000016
Figure PCTCN2019095411-appb-000017
中的一种，所述第二反应物的结构式为
Figure PCTCN2019095411-appb-000018
所述第一中间产物的结构式为
Figure PCTCN2019095411-appb-000019
Figure PCTCN2019095411-appb-000020
Figure PCTCN2019095411-appb-000021
中的一种。
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在第一反应溶液中进行反应生成第一中间产物的步骤可以包括：
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在第一反应溶液中进行反应生成包括第一中间产物的第一混合物；对所述包括第一中间产物的第一混合物进行分离提纯后溶解于第一溶剂得到包括所述第一中间产物的第二混合物。所述第一反应溶液中可以包括水。
所述第一溶剂的体积与所述第一中间产物的摩尔量的对应关系为10毫升-300毫升的第一溶剂对应1毫摩-10毫摩的第一中间产物。具体的，所述第一溶剂的体积与所述第一中间产物的摩尔量的对应关系可以为50毫升的第一溶剂对应3毫摩的第一中间产物。所述第一溶剂的体积与所述第一中间产物的摩尔量的对应关系还可以为200毫升的第一溶剂对应8毫摩的第一中间产物。
以第一反应物
Figure PCTCN2019095411-appb-000022
为例，所述第一反应物和第二反应物在第一反应溶液中进行反应生成第一中间产物的反应式可以为：
Figure PCTCN2019095411-appb-000023
B、提供第三反应物，所述第三反应物和所述第一中间产物在氧化剂的作用下进行反应生成所述电致发光材料，其中，所述第三反应物的结构式为
Figure PCTCN2019095411-appb-000024
所述电致发光材料的结构式为
Figure PCTCN2019095411-appb-000025
Figure PCTCN2019095411-appb-000026
Figure PCTCN2019095411-appb-000027
中的一种。
在所述提供第三反应物，所述第三反应物和所述第一中间产物在氧化剂的作用下进行反应生成所述电致发光材料的步骤中，在第一温度下，将包括催化剂的溶液缓慢加入到所述第二混合物中，然后逐滴加入第三反应物，保持反应温度低于第二温度，搅拌并进行反应。所述第一温度为-10摄氏度至-150摄氏度。所述第二温度为60摄氏度。所述第三反应物的摩尔量和所述第一中间产物的摩尔量为2毫摩-20毫摩的第三反应物对应1毫摩-10毫摩的第一中间产物。
在实际操作中，可以在-30摄氏度-100摄氏度的第一温度下，在氩气环境中将2毫升-10毫升包括催化剂n-BuLi的溶液缓慢加入到包括1毫摩-10毫摩的第一中间产物
Figure PCTCN2019095411-appb-000028
的10毫升-300毫升的四氢呋喃溶液中，逐滴加入2毫摩-20毫摩的第三反应物
Figure PCTCN2019095411-appb-000029
同时保持反应液温度低于第二温度60摄氏度，反应液颜色逐渐变为淡黄色，将反应液冷却至室温并搅拌3小时-24小时，分离提纯得到所述电致发光材料
Figure PCTCN2019095411-appb-000030
在分离提纯中，先将反应混合物用去离子水淬灭，然后用乙酸乙酯萃取以得到的有机相，然后使用MgSO 4对有机相进行干燥并减压浓缩，将残余物溶解在CH 2Cl 2中并加入氧化剂溶液，在室温下搅拌1小时后，收集有机相，再次使用MgSO 4对有机相干燥并减压浓缩，通过柱色谱分离提纯得到所述电致发光材料
Figure PCTCN2019095411-appb-000031
请参阅图1，图1为本申请提供的所述电致发光材料
Figure PCTCN2019095411-appb-000032
在溶液状态和薄膜状态下的电致发光光谱图。所述电致发光材料
Figure PCTCN2019095411-appb-000033
在溶液中最大发射峰位位于456nm处，所述电致发光材料
Figure PCTCN2019095411-appb-000034
在薄膜状态下的最大发射峰位位于479nm。所述电致发光材料属于蓝色发光材料。
请参阅图2，图2为本申请提供一种发光器件100。所述发光器件100包括衬底基板层11、空穴注入层12、空穴传输层13、发光层14、电子注入层15和阴极层16。
所述衬底基板层11包括基板111和阳极层112。所述基板111可以是玻璃基板或透明塑料基板。所述阳极层112设置于所述基板111上。所述阳极层112可以是氧化铟锡材料。所述空穴注入层12设置于所述阳极层112上。所述空穴传输层13设置于所述空穴注入层12上。所述发光层14设置于所述空穴传输层13上。所述发光层14包括所述电致发光材料，所述电致发光材料的结构式为
Figure PCTCN2019095411-appb-000035
Figure PCTCN2019095411-appb-000036
中的一种。
所述电子注入层15设置于所述发光层14上。所述阴极层16设置于所述电子注入层15上。所述阴极层16可以是氟化锂/铝材料。
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，通过选用蒽基团和三苯基氧化膦基团，利用包括蒽基团的分子具有优异的发光特性和在蒽基团的6位和13位附加两个缺电子的三苯基氧化膦基团，其非共面构象有效地阻止了密切分子在固态下的填充、准分子形成和荧光猝灭，实现了一种能发出蓝光的、发光效率高的电致发光材料、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 (18)

  1. 一种电致发光材料，其中，所述电致发光材料的结构式为
    Figure PCTCN2019095411-appb-100001
    Figure PCTCN2019095411-appb-100002
    Figure PCTCN2019095411-appb-100003
                                                   中的一种。
  2. 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在第一反应溶液中进行反应生成第一中间产物，所述第一反应物的结构式为
    Figure PCTCN2019095411-appb-100004
    Figure PCTCN2019095411-appb-100005
    中的一种，所述第二反应物的结构式为
    Figure PCTCN2019095411-appb-100006
    所述第一中间产物的结构式为
    Figure PCTCN2019095411-appb-100007
    Figure PCTCN2019095411-appb-100008
    中的一种；
    提供第三反应物，所述第三反应物和所述第一中间产物在氧化剂的作用下进行反应生成所述电致发光材料，其中，所述第三反应物的结构式为
    Figure PCTCN2019095411-appb-100009
    所述电致发光材料的结构式为
    Figure PCTCN2019095411-appb-100010
    Figure PCTCN2019095411-appb-100011
    Figure PCTCN2019095411-appb-100012
                                          中的一种。
  3. 如权利要求2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在第一反应溶液中进行反应生成第一中间产物的步骤包括：
    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在第一反应溶液中进行反应生成包括第一中间产物的第一混合物；
    对所述包括第一中间产物的第一混合物进行分离提纯后溶解于第一溶剂得到包括所述第一中间产物的第二混合物。
  4. 如权利要求3所述的电致发光材料的制备方法，其中，在所述提供第三反应物，所述第三反应物和所述第一中间产物在氧化剂的作用下进行反应生成所述电致发光材料的步骤中，在第一温度下，将包括催化剂的溶液缓慢加入到所述第二混合物中，然后逐滴加入第三反应物，保持反应温度低于第二温度，搅拌 并进行反应。
  5. 如权利要求4所述的电致发光材料的制备方法，其中，所述第一温度为-10摄氏度至-150摄氏度。
  6. 如权利要求5所述的电致发光材料的制备方法，其中，所述第一温度为-30摄氏度-100摄氏度。
  7. 如权利要求4所述的电致发光材料的制备方法，其中，所述第二温度为60摄氏度。
  8. 如权利要求3所述的电致发光材料的制备方法，其中，在所述提供第三反应物，所述第三反应物和所述第一中间产物在氧化剂的作用下进行反应生成所述电致发光材料中，所述第三反应物的摩尔量和所述第一中间产物的摩尔量为2毫摩-20毫摩的第三反应物对应1毫摩-10毫摩的第一中间产物。
  9. 如权利要求4所述的电致发光材料的制备方法，其中，在所述提供第三反应物，所述第三反应物和所述第一中间产物在氧化剂的作用下进行反应生成所述电致发光材料中，所述第三反应物的摩尔量和所述第一中间产物的摩尔量为2毫摩-20毫摩的第三反应物对应1毫摩-10毫摩的第一中间产物。
  10. 如权利要求3所述的电致发光材料的制备方法，其中，所述第一溶剂的体积与所述第一中间产物的摩尔量的对应关系为10毫升-300毫升的第一溶剂对应1毫摩-10毫摩的第一中间产物。
  11. 如权利要求4所述的电致发光材料的制备方法，其中，所述第一溶剂的体积与所述第一中间产物的摩尔量的对应关系为10毫升-300毫升的第一溶剂对应1毫摩-10毫摩的第一中间产物。
  12. 如权利要求3所述的电致发光材料的制备方法，其中，所述第一溶剂为四氢呋喃。
  13. 如权利要求4所述的电致发光材料的制备方法，其中，所述第一溶剂为四氢呋喃。
  14. 如权利要求3所述的电致发光材料的制备方法，其中，所述第一反应溶液中包括水。
  15. 如权利要求4所述的电致发光材料的制备方法，其中，所述第一反应溶液中包括水。
  16. 如权利要求3所述的电致发光材料的制备方法，其中，所述包括催化剂的溶液为包括催化剂n-BuLi的溶液。
  17. 如权利要求4所述的电致发光材料的制备方法，其中，所述包括催化剂的溶液为包括催化剂n-BuLi的溶液。
  18. 一种发光器件，其中，包括：
    衬底基板层，所述衬底层包括基板和阳极层，所述阳极层设置于所述基板上；
    空穴注入层，所述空穴注入层设置于所述阳极层上；
    空穴传输层，所述空穴传输层设置于所述空穴注入层上；
    发光层，所述发光层设置于所述空穴传输层上；
    电子注入层，所述电子传输层设置于所述发光层上；
    阴极层，所述阴极层设置于所述电子注入层上；
    所述发光层包括所述电致发光材料，所述电致发光材料的结构式为
    Figure PCTCN2019095411-appb-100013
    Figure PCTCN2019095411-appb-100014
    Figure PCTCN2019095411-appb-100015
                                       中的一种。
PCT/CN2019/095411 2019-04-29 2019-07-10 电致发光材料、电致发光材料的制备方法及发光器件 Ceased WO2020220474A1 (zh)

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