WO2020199325A1 - 热激活延迟荧光材料及其制备方法、电致发光器件 - Google Patents

热激活延迟荧光材料及其制备方法、电致发光器件 Download PDF

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WO2020199325A1
WO2020199325A1 PCT/CN2019/087932 CN2019087932W WO2020199325A1 WO 2020199325 A1 WO2020199325 A1 WO 2020199325A1 CN 2019087932 W CN2019087932 W CN 2019087932W WO 2020199325 A1 WO2020199325 A1 WO 2020199325A1
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solution
thermally activated
fluorescent material
activated delayed
delayed fluorescent
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王彦杰
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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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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    • C09K11/00—Luminescent materials, e.g. electroluminescent or chemiluminescent
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  • the invention relates to the field of display technology, in particular to a thermally activated delayed fluorescent material, a preparation method thereof, and an electroluminescent device.
  • OLEDs Organic light-emitting diodes
  • OLEDs due to active light emission, large viewing angle, fast response speed, wide temperature adaptation range, low driving voltage, low power consumption, high brightness, simple production process, light and thin, and can
  • the advantages of flexible display and other advantages have shown great application prospects in the field of OLED display and lighting, attracting the attention of scientific researchers and companies.
  • Samsung and LG have implemented OLEDs in mobile phones.
  • the usual luminescent layer material consists of host and guest luminescent materials, and the luminous efficiency and lifetime of luminescent materials are two important indicators of the quality of luminescent materials.
  • Early OLED light-emitting materials were traditional fluorescent materials.
  • the ratio of singlet and triplet excitons is 1:3, while traditional fluorescent materials can only use singlet excitons to emit light. Therefore, traditional fluorescent
  • the OLED theoretical internal quantum efficiency of the material is 25%. Due to the spin-orbit coupling effect of heavy atoms, metal complex phosphorescent materials can achieve 100% utilization of singlet excitons and triplet excitons; and are now also used in red and green OLED display devices .
  • phosphorescent materials usually use heavy metals such as iridium, platinum, osmium and other precious metals, which are not only costly, but also highly toxic. In addition, efficient and long-life phosphorescent metal complex materials are still a great challenge.
  • the present invention provides a thermally activated delayed fluorescent material and a preparation method thereof, and an electroluminescent device.
  • the structure of the thermally activated delayed fluorescent material is DAA type, where D is an electron donor and A is an electron acceptor .
  • D is an electron donor
  • A is an electron acceptor
  • the present invention provides a thermally activated delayed fluorescent material, which has the following general structural formula:
  • D is an electron donor
  • A is an electron acceptor
  • the electron donor includes one of the following structures:
  • the electron acceptor includes at least one of the following structures:
  • the method for preparing the thermally activated delayed fluorescent material includes the following steps: preparing a format reagent, and placing the format reagent in a first three-necked flask; placing the first reactant and tetrahydrofuran A first solution is obtained from the first reaction flask, wherein the first reactant has the structure of 4-bromophenyl and electron acceptor; the first solution is dropped into the first reaction flask to perform the Grignard reaction , Get the second solution, and stir at room temperature for 1-3 hours, then place the second solution in a dry ice/acetone bath; place trichlorotriazine and tetrahydrofuran in the second reaction flask to obtain the third solution; The second solution was added dropwise to the third solution, and reacted for 2 hours at a temperature of -78°C, then slowly raised to room temperature, and allowed to stand for 12 hours to 24 hours to obtain the fourth solution; the fourth solution was added to distilled water , And extract with
  • the format reagent includes tetrahydrofuran, magnesium and iodine.
  • the step of performing the Grignard reaction includes heating the first three-necked flask to initiate the Grignard reaction at the beginning of the Grignard reaction.
  • the first three The mouth flask was placed in an ice water bath to adjust the reaction temperature.
  • the present invention also provides an electroluminescent device, which includes the thermally activated delayed fluorescent material.
  • the electroluminescent device includes a first electrode; an electron injection layer provided on the first electrode; a hole transport layer provided on the electron injection layer; a light emitting layer, It is arranged on the hole transport layer, and the material used for the light emitting layer includes the thermally activated delayed fluorescent material; the electron transport layer is arranged on the light emitting layer; and the second electrode is arranged on the electron transport layer.
  • the first electrode is an anode, and the material used is indium tin oxide; the second electrode is a cathode, and the material used is one of lithium fluoride or aluminum.
  • the material used for the electron transport layer is 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene
  • the material used for the hole transport layer is 4,4'-cyclohexyl bis[N,N-bis(4-methylphenyl)aniline].
  • the thermally activated delayed fluorescent material of the present invention has an electron acceptor.
  • the electron acceptor effectively increases the electron-withdrawing ability and rigidity of the thermally activated delayed fluorescent material, and can effectively inhibit the non-radiative transition rate, thereby improving the thermally activated delayed fluorescent material.
  • Photoluminescence quantum yield (PLQY) at the same time, it can reduce the electron cloud overlap between the highest occupied molecular orbital (HOMO) and the lowest occupied molecular orbital (LUMO), so as to obtain a smaller minimum singlet and triplet energy level difference ( ⁇ EST), in addition, you can also adjust the emission spectrum of the molecule.
  • the preparation method of the thermally activated delayed fluorescent material of the present invention can effectively improve the synthesis efficiency.
  • the electroluminescent device of the present invention which has the thermally activated delayed fluorescent material of the present invention, can effectively improve the luminous efficiency.
  • Fig. 1 is a fluorescence spectrum diagram of a thermally activated delayed fluorescent material prepared by a preparation method in an embodiment of the present invention.
  • Fig. 2 is a structural diagram of an electroluminescent device in an embodiment of the present invention.
  • the thermally activated delayed fluorescent material of the present invention has the following general structural formula:
  • D is an electron donor
  • A is an electron acceptor
  • the electron donor includes one of the following structures:
  • the electron acceptor includes at least one of the following structures:
  • the molecular structures of the thermally activated delayed fluorescent material in this embodiment are as follows:
  • thermally activated delayed fluorescent material will be further explained below in conjunction with the preparation method of the thermally activated delayed fluorescent material of the present invention.
  • the preparation method of the thermally activated delayed fluorescent material includes the following steps:
  • the format reagent includes tetrahydrofuran, magnesium and iodine.
  • the volume of tetrahydrofuran is 30 ml, and the amount of magnesium is 15 mmol.
  • the first reactant and tetrahydrofuran are placed in the first reaction flask to obtain the first solution, wherein the first reactant has the structure of 4-bromophenyl and electron acceptor.
  • the volume of tetrahydrofuran is 30 ml, and the amount of the substance of the first reactant is 10 mmol; the structural formula of the first reactant is:
  • the first solution was added dropwise to the first reaction flask, and the Grignard reaction was performed to obtain the second solution, which was stirred at room temperature for 1-3 hours, and then the second solution was placed in a dry ice/acetone bath.
  • the first three-necked flask can be heated at the beginning of the Grignard reaction to initiate the Grignard reaction.
  • the first three-necked flask is placed Adjust the reaction temperature in an ice water bath.
  • the second solution was added dropwise to the third solution and reacted for 2 hours at a temperature of -78°C, then slowly raised to room temperature, and allowed to stand for 12 hours to 24 hours to obtain a fourth solution.
  • the fourth solution was added to distilled water and extracted with dichloromethane several times. After each extraction, it was washed with distilled water to obtain the first extract; the first extract was dried with anhydrous sodium sulfate, filtered, and spin-dried. Then use 200-300 mesh silica gel for column chromatography, and rinse with eluent to obtain the intermediate. In this step, the volume of distilled water is 100ml. In this example, the yield of the intermediate is at least 78%.
  • the amount of the intermediate substance is 5 mmol; the amount of pyridine-3-phenylboronic acid is 11 mmol; the volume of toluene is 8 ml; the amount of tetrakis(triphenylphosphorus) palladium is 0.2 mmol.
  • the fifth solution was added to distilled water, and extracted with dichloromethane several times, and washed with distilled water after each extraction to obtain a second extract.
  • the second extract was dried with anhydrous sodium sulfate, filtered, and spin-dried, and then column chromatography was performed with 200-300 mesh silica gel and eluted with eluent to obtain the thermally activated delayed fluorescent material.
  • the production rate of the thermally activated delayed fluorescent material is at least 84%.
  • the structural formula of the thermally activated delayed fluorescent material is:
  • the thermally activated delayed fluorescent material By preparing the thermally activated delayed fluorescent material by the preparation method of this embodiment, the thermally activated delayed fluorescent material can be effectively synthesized, and the synthesis efficiency can be improved.
  • the thermally activated delayed fluorescent material obtained by the preparation method of this embodiment is subjected to spectral experiments and photophysical data detection. Obtain the fluorescence spectrum shown in Figure 1 and the photophysical data shown in Table 1.
  • Table 1 shows the photophysical data of the thermally activated delayed fluorescent material of the present invention.
  • the effective wavelength range of the thermally activated delayed fluorescent material of the present invention is between 500-700, and therefore, the emission spectrum of the molecule can be adjusted within this range. It can be seen from Table 1 that the thermally activated delayed fluorescent material of the present invention has a smaller minimum singlet state and triplet energy difference ( ⁇ E ST ).
  • the present invention also provides an electroluminescent device, which includes the thermally activated delayed fluorescent material.
  • the electroluminescent device includes a first electrode 1, an electron injection layer 2, a hole transport layer 3, a light emitting layer 4, an electron transport layer 5, and a second electrode 6.
  • the electron injection layer 2 is provided on the first electrode 1;
  • the hole transport layer 3 is provided on the electron injection layer 2;
  • the light emitting layer 4 is provided on the hole transport layer 3
  • the material used for the light-emitting layer 4 includes the thermally activated delayed fluorescent material;
  • the electron transport layer 5 is provided on the light-emitting layer 4;
  • the second electrode 6 is provided on the electron transport layer 5.
  • the first electrode 1 is an anode, and the material used is indium tin oxide; the second electrode 6 is a cathode, and the material used is one of lithium fluoride or aluminum.
  • the material used for the electron transport layer 5 is 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene; the hole transport layer 3
  • the material used is 4,4'-cyclohexylbis[N,N-bis(4-methylphenyl)aniline].
  • the electroluminescent device 10 of the present invention adopts the thermally activated delayed fluorescent material in the luminescent layer 4, which effectively improves the luminous efficiency of the electroluminescent device 10.

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Abstract

一种热激活延迟荧光材料，包含三嗪基母核以及连接于该母核的电子给体和电子受体，能够抑制非辐射跃迁速率。电致发光器件包含所述热激活延迟荧光材料，能够有效提高发光效率。

Description

热激活延迟荧光材料及其制备方法、电致发光器件 技术领域
本发明涉及显示技术领域，具体为一种热激活延迟荧光材料及其制备方法、电致发光器件。
背景技术
有机发光二极管(organic lighting-emitting diodes,OLEDs)，由于主动发光、可视角度大、相应速度快、温度适应范围宽、驱动电压低、功耗小、亮度大、生产工艺简单、轻薄、且可以柔性显示等优点，在OLED显示和照明领域表现出巨大的应用前景，吸引了科研工作者和公司的关注。目前，三星、LG已经实现OLEDs应用在手机上。在OLED中，发光层材料的优劣是OLED能否产业化起决定作用。通常的发光层材料由主体和客体发光材料，而发光材料的发光效率和寿命是发光材料好坏的两个重要指标。早期的OLED发光材料为传统荧光材料，由于在OLED显示装置中，单重态和三重态的激子比例为1:3，而传统荧光材料只能利用单重态激子发光，因此，传统荧光材料的OLED理论内量子效率为25％。金属配合物磷光材料由于重原子的自旋轨道耦合效应，使得其能够实现单重态激子和三重态激子的100％利用率；并且现在也已经用在红光和绿光OLED显示装置上。但是，磷光材料通常要使用重金属铱、铂、锇等贵重金属，不仅成本高，而且毒性较 大。此外，高效、长寿命的磷光金属配合物材料仍旧是极大的挑战。
技术问题
为解决上述技术问题：本发明提供一种热激活延迟荧光材料及其制备方法、电致发光器件，热激活延迟荧光材料的结构为D-A-A型，其中，D为电子给体，A为电子受体，通过电子受体而增加吸电子能力和刚性，能够有效抑制非辐射跃迁速率，从而提高分子的光致发光量子产率；同时减小最高占有分子轨道(HOMO)和最低占有分子轨道(LUMO)之间的电子云重叠，从而获得较小的三重能级差，此外，还可以调节发光光谱。
技术解决方案
解决上述问题的技术方案是：本发明提供一种热激活延迟荧光材料，具有以下结构通式：
Figure PCTCN2019087932-appb-000001
所述结构通式中，D为电子给体，A为电子受体。
在本发明一实施例中，所述电子给体包括以下结构中的一种：
Figure PCTCN2019087932-appb-000002
在本发明一实施例中，所述电子受体包括以下结构中的至少一种：
Figure PCTCN2019087932-appb-000003
Figure PCTCN2019087932-appb-000004
在本发明一实施例中，所述的热激活延迟荧光材料的制备方法，包括以下步骤：制备格式试剂，并将格式试剂置于第一三口烧瓶中；将第一反应剂和四氢呋喃置于第一反应瓶中得到第一溶液，其中第一反应剂具有4-溴代苯基和电子受体的结构；将所述第一溶液滴加至所述第一反应瓶中，进行格氏反应，得到第二溶液，并在室温下搅拌1-3小时，然后将第二溶液置于干冰/丙酮浴中；将三氯三嗪和四氢呋喃置于第二反应瓶中得到第三溶液；将第二溶液滴加至所述第三溶液中，并在温度-78℃条件下反应2小时，然后缓慢升至室温，静置12小时-24小时，得到第四溶液；将第四溶液加入蒸馏水中，并用二氯甲烷萃取多次，每次萃取后用蒸馏水进行水洗，得到第一萃取液；将所述第一萃取液用无水硫酸钠干燥，过滤，旋干，之后用200-300目的硅胶进行柱层析，并用淋洗液淋洗，得到中间体；将所述中间体、吡啶-3-苯硼酸、甲苯、碳酸钠水溶液加入至第二三口烧瓶中，用氩气进行抽换气；将四(三苯基磷)合钯加入至第二三口烧瓶中，在温度为75℃-85℃条件下回流反应24h，冷却至室温后得到第五溶液；将第五溶液加入蒸馏水中，并用二氯甲烷萃取多次，每次萃取后用蒸馏水进行水洗，得到第二萃取液；将所述第二萃取液用无水硫酸钠干燥，过滤，旋干，之后用200-300目的硅胶进行柱层析，并用淋洗液淋洗，得到所述热激活延迟荧光材料。
在本发明一实施例中，所述格式试剂中包括四氢呋喃、镁以及碘。
在本发明一实施例中，在进行格氏反应步骤中，包括在进行格式反应开始阶段，对第一三口烧瓶进行加热引发格氏反应，在格氏反应过程中，将所述第一三口烧瓶置于冰水浴中，调节反应温度。
本发明还提供了一种电致发光器件，包括所述的热激活延迟荧光材料。
在本发明一实施例中，所述的电致发光器件包括第一电极；电子注入层，设于所述第一电极上；空穴传输层，设于所述电子注入层上；发光层，设于所述空穴传输层上，所述发光层所用材料包括所述热激活延迟荧光材料；电子传输层，设于发光层上；第二电极，设于所述电子传输层上。
在本发明一实施例中，所述第一电极为阳极，其所用材料为氧化铟锡；所述第二电极为阴极，其所用材料为氟化锂或铝中的一种。
在本发明一实施例中，所述电子传输层所用材料为2,3,6,7,10,11-六氰基-1,4,5,8,9,12-六氮杂苯并菲；所述空穴传输层所用材料为4,4'-环己基二[N,N-二(4-甲基苯基)苯胺]。
有益效果
本发明的热激活延迟荧光材料，其具有电子受体，通过电子受体有效增加了热激活延迟荧光材料的吸电子能力和刚性，能够有效抑制非辐射跃迁速率，从而提高热激活延迟荧光材料的光致发光量子产率(PLQY)；同时能够减小最高占有分子轨道(HOMO)和最低占有分子轨道(LUMO)之间的电子云重叠，从而获得较小的最低单重 态和三重能级差(ΔEST)，此外，还可以调节分子的发光光谱。本发明的热激活延迟荧光材料的制备方法，能够有效的提高了合成效率。本发明的电致发光器件，其具有本发明的热激活延迟荧光材料，能够有效的提高发光效率。
附图说明
为了更清楚地说明本发明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发明的一些实施例，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。
下面结合附图和实施例对本发明作进一步解释。
图1是本发明实施例中的制备方法制得的热激活延迟荧光材料的荧光光谱图。
图2是本发明实施例中电致发光器件结构图。
附图标记：
10电致发光器件；
1第一电极；                 2电子注入层；
3空穴传输层；               4发光层；
5电子传输层；               6第二电极。
本发明的实施方式
下面详细描述本发明的实施方式，所述实施方式的示例在附图中示出，其中自始至终相同或类似的标号表示相 同或类似的元件或具有相同或类似功能的元件。下面通过参考附图描述的实施方式是示例性的，仅用于解释本发明，而不能理解为对本发明的限制。
以下实施例的说明是参考附加的图式，用以例示本发明可用以实施的特定实施例。本发明所提到的方向用语，例如「上」、「下」、「前」、「后」、「左」、「右」、「顶」、「底」等，仅是参考附加图式的方向。因此，使用的方向用语是用以说明及理解本发明，而非用以限制本发明。
本发明的热激活延迟荧光材料，具有以下结构通式：
Figure PCTCN2019087932-appb-000005
所述结构通式中，D为电子给体，A为电子受体。
本实施例中，所述电子给体包括以下结构中的一种：
Figure PCTCN2019087932-appb-000006
Figure PCTCN2019087932-appb-000007
本实施例中，所述电子受体包括以下结构中的至少一种：
Figure PCTCN2019087932-appb-000008
通过电子给体和电子受体的排列组合，总有若干种(90种或以上)不同结构的热激活延迟荧光材料。
以电子给体：9,9-二甲基吖啶为例，本实施例中的热激活延迟荧光材料的分子结构具有如下几种：
Figure PCTCN2019087932-appb-000009
为了更加清楚的解释本发明，下面结合本发明的热激活延迟荧光材料制备方法对所述热激活延迟荧光材料进行进一步解释。
所述的热激活延迟荧光材料的制备方法，包括以下步骤：
制备格式试剂，并将格式试剂置于第一三口烧瓶中。所述格式试剂中包括四氢呋喃、镁以及碘。本步骤中，四氢呋喃的体积为30ml，镁的物质的量为15mmol。
将第一反应剂和四氢呋喃置于第一反应瓶中得到第一溶液，其中第一反应剂具有4-溴代苯基和电子受体的结构。本步骤中，四氢呋喃的体积为30ml，第一反应剂的物质的量为10mmol；所述第一反应 剂的结构式为：
Figure PCTCN2019087932-appb-000010
将所述第一溶液滴加至所述第一反应瓶中，进行格氏反应，得到第二溶液，并在室温下搅拌1-3小时，然后将第二溶液置于干冰/丙酮浴中。在进行格氏反应时，若开始难以引发反应，可在进行格式反应开始阶段，对第一三口烧瓶进行加热引发格氏反应，在格氏反应过程中，将所述第一三口烧瓶置于冰水浴中，调节反应温度。
将三氯三嗪和四氢呋喃置于第二反应瓶中得到第三溶液。本步骤中，三氯三嗪的物质的量为10mmol，四氢呋喃的体积为50ml。
将第二溶液滴加至所述第三溶液中，并在温度-78℃条件下反应2小时，然后缓慢升至室温，静置12小时-24小时，得到第四溶液。
将第四溶液加入蒸馏水中，并用二氯甲烷萃取多次，每次萃取后用蒸馏水进行水洗，得到第一萃取液；将所述第一萃取液用无水硫酸钠干燥，过滤，旋干，之后用200-300目的硅胶进行柱层析，并用淋洗液淋洗，得到中间体。本步骤中，蒸馏水体积为100ml。本实施例中，中间体的制得率最低为78％。
所述中间体的结构式如下：
Figure PCTCN2019087932-appb-000011
将所述中间体、吡啶-3-苯硼酸、甲苯、碳酸钠水溶液加入至第二三口烧瓶中，用氩气进行抽换气；将四(三苯基磷)合钯加入至第二三口烧瓶中，在温度为75℃-85℃条件下回流反应24h，冷却至室温后得到第五溶液。本实施例中，所述中间体的物质的量为5mmol；吡啶-3-苯硼酸的物质的量为11mmol；甲苯的体积为8ml；四(三苯基磷)合钯的物质的量为0.2mmol。
将第五溶液加入蒸馏水中，并用二氯甲烷萃取多次，每次萃取后用蒸馏水进行水洗，得到第二萃取液。
将所述第二萃取液用无水硫酸钠干燥，过滤，旋干，之后用200-300目的硅胶进行柱层析，并用淋洗液淋洗，得到所述热激活延迟荧光材料，本实施例中，所述热激活延迟荧光材料的制得率最低为84％。
所述热激活延迟荧光材料的结构式为：
Figure PCTCN2019087932-appb-000012
通过本实施例的制备方法制备热激活延迟荧光材料，能够有效合成热激活延迟荧光材料，同时能够提高合成效率。
为了验证本发明的热激活延迟荧光材料的特性是否满足电致发光器件的要求，因此本实施例中将通过本实施例的制备方法得到的热激活延迟荧光材料进行光谱实验和光物理数据检测。得到如图1所示的荧光光谱图以及如表1所示的光物理数据。
表1为本发明的热激活延迟荧光材料的光物理数据。
  PL Peak(nm) S 1(eV) T 1(eV) E ST(eV) PLQY(％)
热激活延迟荧光材料 586 2.35 2.29 0.06 90
由图1可知，本发明的热激活延迟荧光材料的有效波长范围在500-700之间，因此，可以在此范围内调节分子的发光光谱。由表1可知，本发明的热激活延迟荧光材料具有较小的最低单重态和三重能级差(ΔE ST)。
如图2所示，本发明还提供了一种电致发光器件，包括所述的热激活延迟荧光材料。
所述的电致发光器件包括第一电极1、电子注入层2、空穴传输层3、发光层4、电子传输层5、第二电极6。其中，所述电子注入层 2设于所述第一电极1上；所述空穴传输层3设于所述电子注入层2上；所述发光层4设于所述空穴传输层3上，所述发光层4所用材料包括所述热激活延迟荧光材料；所述电子传输层5设于所述发光层4上；所述第二电极6设于所述电子传输层5上。
本实施例中，所述第一电极1为阳极，其所用材料为氧化铟锡；所述第二电极6为阴极，其所用材料为氟化锂或铝中的一种。所述电子传输层5所用材料为2,3,6,7,10,11-六氰基-1,4,5,8,9,12-六氮杂苯并菲；所述空穴传输层3所用材料为4,4'-环己基二[N,N-二(4-甲基苯基)苯胺]。
本发明的电致发光器件10，在发光层4采用所述的热激活延迟荧光材料，有效的提高了电致发光器件10的发光效率。
以上仅为本发明的较佳实施例而已，并不用以限制本发明，凡在本发明的精神和原则之内所作的任何修改、等同替换和改进等，均应包含在本发明的保护范围之内。

Claims (10)

  1. 一种热激活延迟荧光材料，其具有以下结构通式：
    Figure PCTCN2019087932-appb-100001
    所述结构通式中，D为电子给体，A为电子受体。
  2. 根据权利要求1所述的热激活延迟荧光材料，其中，所述电子给体包括以下结构中的一种：
    Figure PCTCN2019087932-appb-100002
  3. 根据权利要求1所述的热激活延迟荧光材料，其中，所述电子受体包括以下结构中的至少一种：
    Figure PCTCN2019087932-appb-100003
  4. 一种制备方法，用来制作如权利要求1所述的热激活延迟荧光材料，其中，所述制备方法包括以下步骤：
    制备格式试剂，并将格式试剂置于第一三口烧瓶中；
    将第一反应剂和四氢呋喃置于第一反应瓶中得到第一溶液，其中第一反应剂具有4-溴代苯基和电子受体的结构；
    将所述第一溶液滴加至所述第一反应瓶中，进行格氏反应，得到第二溶液，并在室温下搅拌1-3小时，然后将第二溶液置于干冰/丙酮浴中；
    将三氯三嗪和四氢呋喃置于第二反应瓶中得到第三溶液；
    将第二溶液滴加至所述第三溶液中，并在温度-78℃条件下反应2小 时，然后缓慢升至室温，静置12小时-24小时，得到第四溶液；
    将第四溶液加入蒸馏水中，并用二氯甲烷萃取多次，每次萃取后用蒸馏水进行水洗，得到第一萃取液；
    将所述第一萃取液用无水硫酸钠干燥，过滤，旋干，之后用200-300目的硅胶进行柱层析，并用淋洗液淋洗，得到中间体；
    将所述中间体、吡啶-3-苯硼酸、甲苯、碳酸钠水溶液加入至第二三口烧瓶中，用氩气进行抽换气；
    将四(三苯基磷)合钯加入至第二三口烧瓶中，在温度为75℃-85℃条件下回流反应24h，冷却至室温后得到第五溶液；
    将第五溶液加入蒸馏水中，并用二氯甲烷萃取多次，每次萃取后用蒸馏水进行水洗，得到第二萃取液；
    将所述第二萃取液用无水硫酸钠干燥，过滤，旋干，之后用200-300目的硅胶进行柱层析，并用淋洗液淋洗，得到所述热激活延迟荧光材料。
  5. 根据权利要求4所述的制备方法，其中，所述格式试剂中包括四氢呋喃、镁以及碘。
  6. 根据权利要求4所述的制备方法，其中，在进行格氏反应步骤中，包括在进行格式反应开始阶段，对第一三口烧瓶进行加热引发格氏反应，在格氏反应过程中，将所述第一三口烧瓶置于冰水浴中，调节反应温度。
  7. 一种电致发光器件，其包括如权利要求1所述的热激活延迟荧光材料。
  8. 根据权利要求7所述的电致发光器件，其包括
    第一电极；
    电子注入层，设于所述第一电极上；
    空穴传输层，设于所述电子注入层上；
    发光层，设于所述空穴传输层上，所述发光层所用材料包括所述热激活延迟荧光材料；
    电子传输层，设于发光层上；
    第二电极，设于所述电子传输层上。
  9. 根据权利要求8所述的电致发光器件，其中，所述第一电极为阳极，其所用材料为氧化铟锡；所述第二电极为阴极，其所用材料为氟化锂或铝中的一种。
  10. 根据权利要求8所述的电致发光器件，其中，所述电子传输层所用材料为2,3,6,7,10,11-六氰基-1,4,5,8,9,12-六氮杂苯并菲；所述空穴传输层所用材料为4,4'-环己基二[N,N-二(4-甲基苯基)苯胺]。
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