WO2020211181A1 - Thermally-activated delayed fluorescent material and organic light emitting diode display device - Google Patents

Thermally-activated delayed fluorescent material and organic light emitting diode display device Download PDF

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WO2020211181A1
WO2020211181A1 PCT/CN2019/091050 CN2019091050W WO2020211181A1 WO 2020211181 A1 WO2020211181 A1 WO 2020211181A1 CN 2019091050 W CN2019091050 W CN 2019091050W WO 2020211181 A1 WO2020211181 A1 WO 2020211181A1
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activated delayed
fluorescent material
delayed fluorescent
thermally activated
emitting diode
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罗佳佳
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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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Definitions

  • the invention relates to the technical field of an organic photoelectric material, in particular to a thermally activated delayed fluorescent material and an organic light-emitting diode display device.
  • the light-emitting guest material is one of the main factors affecting the luminous efficiency of organic light-emitting diode display devices.
  • the light-emitting guest materials used in organic light-emitting diode display devices are fluorescent materials.
  • the ratio of singlet and triplet excitons in organic light-emitting diode display devices is 1:3. Therefore, the internal The quantum efficiency (internal quantum efficiency, IQE) can only reach 25%, and the application of fluorescent electroluminescent devices is limited.
  • the heavy metal complex phosphorescent material is based on the spin-orbit coupling of heavy atoms, so it can simultaneously utilize singlet and triplet excitons to achieve 100% internal quantum efficiency.
  • the commonly used heavy metals are precious metals such as iridium (Ir) or platinum (Pt), and the phosphorescent materials of heavy metal complexes need to be improved in terms of blue light materials.
  • Pure organic thermally activated delayed fluorescent materials have a low lowest single-triplet energy gap ( ⁇ EST), and triplet excitons can pass through reverse intersystem crossing (RISC). To the singlet state, and then through the radiation transition to the ground state to emit light, so that the singlet excitons and triplet excitons can be used at the same time, and 100% internal quantum efficiency can also be achieved.
  • RISC reverse intersystem crossing
  • thermally activated delayed fluorescent materials For thermally activated delayed fluorescent materials, high reverse intersystem crossing constant and high photoluminescence quantum yield are necessary conditions for the preparation of high-efficiency organic light-emitting diode display devices. At present, compared with heavy metal complexes, thermally activated delayed fluorescent materials with the above conditions are still relatively lacking. Therefore, it is necessary to provide a novel thermally activated delayed fluorescent material to solve the problems existing in the prior art.
  • the embodiment of the present invention provides a thermally activated delayed fluorescent material, including the structure shown in formula (I):
  • R is selected from oxygen, sulfur or C1-C3 alkyl.
  • the thermally activated delayed fluorescent material is as follows:
  • the thermally activated delayed fluorescent material is as follows:
  • the thermally activated delayed fluorescent material is as follows:
  • an organic light emitting diode display device including an anode, a cathode, and an organic functional layer located between the anode and the cathode.
  • the organic functional layer includes a thermally activated delayed fluorescent material, and the thermally activated delayed fluorescent material includes the formula ( I) Structure shown:
  • R is selected from oxygen, sulfur or C1-C3 alkyl.
  • the thermally activated delayed fluorescent material is as follows:
  • the thermally activated delayed fluorescent material is as follows:
  • the thermally activated delayed fluorescent material is as follows:
  • the thermally activated delayed fluorescent material is used as the fluorescent host material in the organic light emitting diode display device.
  • the thermally activated delayed fluorescent material is used as an electron transport material in an organic light emitting diode display device.
  • an organic light emitting diode display device including an anode, a cathode, and an organic functional layer located between the anode and the cathode.
  • the organic functional layer includes a thermally activated delayed fluorescent material, and the thermally activated delayed fluorescent material includes the formula ( I) Structure shown:
  • R is selected from oxygen, sulfur or C1-C3 alkyl
  • the thermally activated delayed fluorescent material is used as a fluorescent host material and an electron transport material in an organic light emitting diode display device.
  • the thermally activated delayed fluorescent material is as follows:
  • the thermally activated delayed fluorescent material is as follows:
  • the thermally activated delayed fluorescent material is as follows:
  • the thermally activated delayed fluorescent material of the present invention has the properties of lower lowest single triplet energy level difference, high reverse intersystem crossing constant and high photoluminescence quantum yield, thereby achieving high Luminous efficiency organic light emitting diode display device.
  • Figure 1 is an embodiment of the present invention Distribution map of the highest electron occupied orbital (HOMO) and lowest electron unoccupied orbital (LUMO);
  • Figure 2 is an embodiment of the present invention Distribution map of the highest electron occupied orbital (HOMO) and lowest electron unoccupied orbital (LUMO);
  • Figure 3 is an embodiment of the present invention Distribution map of the highest electron occupied orbital (HOMO) and lowest electron unoccupied orbital (LUMO);
  • Fig. 4 is a photoluminescence spectrum of a thermally activated delayed fluorescent material in a toluene solution according to an embodiment of the present invention.
  • FIG. 5 is a schematic diagram of an organic light emitting diode display device with a thermally activated delayed fluorescent material as a light emitting layer according to an embodiment of the present invention.
  • thermally activated delayed fluorescent materials have a molecular structure in which an electron donor and an electron acceptor are combined.
  • the embodiment of the present invention changes the structure of the electron acceptor unit so that the electron acceptor unit has different electron accepting capabilities and increases the thermal activation delay.
  • the luminous efficiency of the fluorescent material thereby realizing an organic light emitting diode display device with high luminous efficiency.
  • the embodiment of the present invention provides a thermally activated delayed fluorescent material, including the structure shown in formula (I):
  • R is selected from oxygen, sulfur or C1-C3 alkyl.
  • the thermally activated delayed fluorescent material is selected from and The group formed.
  • thermally activated delayed fluorescent materials according to different embodiments of the present invention are further described below.
  • the lowest singlet state (S1) and lowest triplet energy level (T1) of, the electrochemical energy levels are shown in Table 2 below:
  • Figure 3 is an embodiment of the present invention The highest electron occupied orbital (HOMO) and lowest electron unoccupied orbital (LUMO) distribution diagrams of.
  • HOMO highest electron occupied orbital
  • LUMO lowest electron unoccupied orbital
  • FIG. 4 is a photoluminescence spectrum of thermally activated delayed fluorescent materials (compound I, compound II, and compound II) in a toluene solution according to an embodiment of the present invention.
  • an organic light emitting diode display device including an anode, a cathode, and an organic functional layer located between the anode and the cathode.
  • the organic functional layer includes a thermally activated delayed fluorescent material.
  • the thermally activated delayed fluorescent material includes the following Structure:
  • the thermally activated delayed fluorescent material having the above chemical structure can be used as a fluorescent host material or an electron transporting material in an organic light emitting diode display device.
  • an organic light emitting diode display device with a thermally activated delayed fluorescent material as a light emitting layer of an embodiment of the present invention includes a glass and conductive glass (ITO) layer 10, a hole injection layer 20, a hole transport layer 30, a light emitting layer 40, Electron transport layer 50 and cathode layer 60.
  • the organic light emitting diode display device can be completed according to the method known in the technical field of the present invention, so it will not be repeated.
  • the current, brightness and voltage characteristics of the organic light-emitting diode display device are completed by the Keithley source measurement system (Keithley 2400 Sourcemeter, Keithley 2000 Currentmeter) with a calibrated silicon photodiode.
  • the electroluminescence spectrum is performed by the French JY company SPEX CCD3000 All measurements measured by the spectrometer are done under normal atmospheric pressure and room temperature.
  • the thermally activated delayed fluorescent material of the present invention has the properties of low energy level difference of the lowest single triplet state, high reverse system crossover constant and high photoluminescence quantum yield, thereby realizing an organic light emitting diode with high luminous efficiency display screen.

Abstract

Disclosed by the present invention are a thermally-activated delayed fluorescent material and an organic light emitting diode display device, the thermally activated delayed fluorescent material having the structure represented by formula (I), wherein R is selected as an alkyl group of oxygen, sulfur or C1-C3.

Description

热活化延迟荧光材料及有机发光二极管显示设备Thermally activated delayed fluorescent material and organic light emitting diode display device 技术领域Technical field
本发明是有关于一种有机光电材料技术领域，特别是有关于一种热活化延迟荧光材料及有机发光二极管显示设备。The invention relates to the technical field of an organic photoelectric material, in particular to a thermally activated delayed fluorescent material and an organic light-emitting diode display device.
背景技术Background technique
发光客体材料是影响有机发光二极管显示设备发光效率的主要因素之一。一般而言，有机发光二极管显示设备使用的发光客体材料为荧光材料，通常在有机发光二极管显示设备中的单重态和三重态的激子比例为1:3，因此有机发光二极管显示设备的内量子效率(internal quantum efficiency,IQE)只能达到25％，荧光电致发光器件的应用受到限制。重金属配合物磷光材料基于重原子的自旋轨道耦合作用，因此能够同时利用单重态和三重态激子而实现100％的内量子效率。然而，通常使用的重金属都是铱(Ir)或铂(Pt)等贵重金属，并且重金属配合物磷光发光材料在蓝光材料方面还须改良。纯有机热活化延迟荧光材料具有较低的最低单三重态的能级差(Lowest single-triplet energy gap(ΔEST))，三重态激子可以通过反向系间窜越(reverse intersystem crossing,RISC)回到单重态，再通过辐射跃迁至基态而发光，从而能够同时利用单重态激子及三重态激子，也可以实现100％的内量子效率。The light-emitting guest material is one of the main factors affecting the luminous efficiency of organic light-emitting diode display devices. Generally speaking, the light-emitting guest materials used in organic light-emitting diode display devices are fluorescent materials. Usually, the ratio of singlet and triplet excitons in organic light-emitting diode display devices is 1:3. Therefore, the internal The quantum efficiency (internal quantum efficiency, IQE) can only reach 25%, and the application of fluorescent electroluminescent devices is limited. The heavy metal complex phosphorescent material is based on the spin-orbit coupling of heavy atoms, so it can simultaneously utilize singlet and triplet excitons to achieve 100% internal quantum efficiency. However, the commonly used heavy metals are precious metals such as iridium (Ir) or platinum (Pt), and the phosphorescent materials of heavy metal complexes need to be improved in terms of blue light materials. Pure organic thermally activated delayed fluorescent materials have a low lowest single-triplet energy gap (ΔEST), and triplet excitons can pass through reverse intersystem crossing (RISC). To the singlet state, and then through the radiation transition to the ground state to emit light, so that the singlet excitons and triplet excitons can be used at the same time, and 100% internal quantum efficiency can also be achieved.
技术问题technical problem
针对热活化延迟荧光材料，高反向系间窜越常数以及高光致发光量子产率是制备高效率有机发光二极管显示设备的必要条件。目前，具备上述条件的热活化延迟荧光材料相对于重金属配合物而言还是比较缺乏。故，有必要提供一种新颖的热活化延迟荧光材料，以解决现有技术所存在的问题。For thermally activated delayed fluorescent materials, high reverse intersystem crossing constant and high photoluminescence quantum yield are necessary conditions for the preparation of high-efficiency organic light-emitting diode display devices. At present, compared with heavy metal complexes, thermally activated delayed fluorescent materials with the above conditions are still relatively lacking. Therefore, it is necessary to provide a novel thermally activated delayed fluorescent material to solve the problems existing in the prior art.
技术解决方案Technical solutions
本发明实施例提供一种热活化延迟荧光材料，包括如式(I)所示的结构:The embodiment of the present invention provides a thermally activated delayed fluorescent material, including the structure shown in formula (I):
Figure PCTCN2019091050-appb-000001
Figure PCTCN2019091050-appb-000001
其中，R选自氧、硫或C1-C3的烷基。Wherein, R is selected from oxygen, sulfur or C1-C3 alkyl.
在本发明的一实施例中，热活化延迟荧光材料如下所示：In an embodiment of the present invention, the thermally activated delayed fluorescent material is as follows:
Figure PCTCN2019091050-appb-000002
Figure PCTCN2019091050-appb-000002
在本发明的一实施例中，热活化延迟荧光材料如下所示：In an embodiment of the present invention, the thermally activated delayed fluorescent material is as follows:
Figure PCTCN2019091050-appb-000003
Figure PCTCN2019091050-appb-000003
在本发明的一实施例中，所述热活化延迟荧光材料如下所示：In an embodiment of the present invention, the thermally activated delayed fluorescent material is as follows:
Figure PCTCN2019091050-appb-000004
Figure PCTCN2019091050-appb-000004
本发明另一实施例提供一种有机发光二极管显示设备，包括阳极、阴极以及位于阳极与阴极之间的有机功能层，有机功能层包括热活化延迟荧光材料，热活化延迟荧光材料包括如式(I)所示的结构:Another embodiment of the present invention provides an organic light emitting diode display device, including an anode, a cathode, and an organic functional layer located between the anode and the cathode. The organic functional layer includes a thermally activated delayed fluorescent material, and the thermally activated delayed fluorescent material includes the formula ( I) Structure shown:
Figure PCTCN2019091050-appb-000005
Figure PCTCN2019091050-appb-000005
其中，R选自氧、硫或C1-C3的烷基。Wherein, R is selected from oxygen, sulfur or C1-C3 alkyl.
在本发明的一实施例中，热活化延迟荧光材料如下所示：In an embodiment of the present invention, the thermally activated delayed fluorescent material is as follows:
Figure PCTCN2019091050-appb-000006
Figure PCTCN2019091050-appb-000006
在本发明的一实施例中，热活化延迟荧光材料如下所示：In an embodiment of the present invention, the thermally activated delayed fluorescent material is as follows:
Figure PCTCN2019091050-appb-000007
Figure PCTCN2019091050-appb-000007
在本发明的一实施例中，热活化延迟荧光材料如下所示：In an embodiment of the present invention, the thermally activated delayed fluorescent material is as follows:
Figure PCTCN2019091050-appb-000008
Figure PCTCN2019091050-appb-000008
在本发明的一实施例中，热活化延迟荧光材料在有机发光二极管显示设备中作为荧光主体材料。In an embodiment of the present invention, the thermally activated delayed fluorescent material is used as the fluorescent host material in the organic light emitting diode display device.
在本发明的一实施例中，热活化延迟荧光材料在有机发光二极管显示设备中作为电子传输材料。In an embodiment of the present invention, the thermally activated delayed fluorescent material is used as an electron transport material in an organic light emitting diode display device.
本发明另一实施例提供一种有机发光二极管显示设备，包括阳极、阴极以及位于阳极与阴极之间的有机功能层，有机功能层包括热活化延迟荧光材料，热活化延迟荧光材料包括如式(I)所示的结构:Another embodiment of the present invention provides an organic light emitting diode display device, including an anode, a cathode, and an organic functional layer located between the anode and the cathode. The organic functional layer includes a thermally activated delayed fluorescent material, and the thermally activated delayed fluorescent material includes the formula ( I) Structure shown:
Figure PCTCN2019091050-appb-000009
Figure PCTCN2019091050-appb-000009
其中，R选自氧、硫或C1-C3的烷基，热活化延迟荧光材料在有机发光二极管显示设备中作为荧光主体材料和电子传输材料。Wherein, R is selected from oxygen, sulfur or C1-C3 alkyl, and the thermally activated delayed fluorescent material is used as a fluorescent host material and an electron transport material in an organic light emitting diode display device.
在本发明的一实施例中，热活化延迟荧光材料如下所示：In an embodiment of the present invention, the thermally activated delayed fluorescent material is as follows:
Figure PCTCN2019091050-appb-000010
Figure PCTCN2019091050-appb-000010
在本发明的一实施例中，热活化延迟荧光材料如下所示：In an embodiment of the present invention, the thermally activated delayed fluorescent material is as follows:
Figure PCTCN2019091050-appb-000011
Figure PCTCN2019091050-appb-000011
在本发明的一实施例中，热活化延迟荧光材料如下所示：In an embodiment of the present invention, the thermally activated delayed fluorescent material is as follows:
Figure PCTCN2019091050-appb-000012
Figure PCTCN2019091050-appb-000012
有益效果Beneficial effect
相较于先前技术，本发明的热活化延迟荧光材料具有较低的最低单三重态的能级差、高反向系间窜越常数及高的光致发光量子产率的性质，进而实现具有高发光效率的有机发光二极管显示设备。Compared with the prior art, the thermally activated delayed fluorescent material of the present invention has the properties of lower lowest single triplet energy level difference, high reverse intersystem crossing constant and high photoluminescence quantum yield, thereby achieving high Luminous efficiency organic light emitting diode display device.
附图说明Description of the drawings
图1是本发明实施例的
Figure PCTCN2019091050-appb-000013
的最高电子占据轨道(HOMO)与最低电子未占据轨道(LUMO)分布图； Figure 1 is an embodiment of the present invention
Figure PCTCN2019091050-appb-000013
Distribution map of the highest electron occupied orbital (HOMO) and lowest electron unoccupied orbital (LUMO);
图2是本发明实施例的
Figure PCTCN2019091050-appb-000014
的最高电子占据轨道(HOMO)与最低电子未占据轨道(LUMO)分布图； Figure 2 is an embodiment of the present invention
Figure PCTCN2019091050-appb-000014
Distribution map of the highest electron occupied orbital (HOMO) and lowest electron unoccupied orbital (LUMO);
图3是本发明实施例的
Figure PCTCN2019091050-appb-000015
的最高电子占据轨道(HOMO)与最低电子未占据轨道(LUMO)分布图； Figure 3 is an embodiment of the present invention
Figure PCTCN2019091050-appb-000015
Distribution map of the highest electron occupied orbital (HOMO) and lowest electron unoccupied orbital (LUMO);
图4是本发明实施例的热活化延迟荧光材料在甲苯溶液中的光致发光光谱；以及Fig. 4 is a photoluminescence spectrum of a thermally activated delayed fluorescent material in a toluene solution according to an embodiment of the present invention; and
图5是本发明实施例的热活化延迟荧光材料作为发光层的有机发光二极管显示设备的示意图。FIG. 5 is a schematic diagram of an organic light emitting diode display device with a thermally activated delayed fluorescent material as a light emitting layer according to an embodiment of the present invention.
本发明的实施方式Embodiments of the invention
一般热活化延迟荧光材料具有电子给体和电子受体相结合的分子结构，本发明实施例通过改变电子受体单元的结构，使得电子受体单元具有不同的电子接受能力，并增加热活化延迟荧光材料的发光效率，进而实现具有高发光效率的有机发光二极管显示设备。Generally, thermally activated delayed fluorescent materials have a molecular structure in which an electron donor and an electron acceptor are combined. The embodiment of the present invention changes the structure of the electron acceptor unit so that the electron acceptor unit has different electron accepting capabilities and increases the thermal activation delay. The luminous efficiency of the fluorescent material, thereby realizing an organic light emitting diode display device with high luminous efficiency.
本发明实施例提供一种热活化延迟荧光材料，包括如式(I)所示的结构:The embodiment of the present invention provides a thermally activated delayed fluorescent material, including the structure shown in formula (I):
Figure PCTCN2019091050-appb-000016
Figure PCTCN2019091050-appb-000016
其中，R选自氧、硫或C1-C3的烷基。优选地，热活化延迟荧光材料是选自于由
Figure PCTCN2019091050-appb-000017
及
Figure PCTCN2019091050-appb-000018
所组成的群组。 Wherein, R is selected from oxygen, sulfur or C1-C3 alkyl. Preferably, the thermally activated delayed fluorescent material is selected from
Figure PCTCN2019091050-appb-000017
and
Figure PCTCN2019091050-appb-000018
The group formed.
以下进一步描述本发明不同实施例的热活化延迟荧光材料的合成步骤。The synthesis steps of thermally activated delayed fluorescent materials according to different embodiments of the present invention are further described below.
Figure PCTCN2019091050-appb-000019
的合成步骤如下所示：
Figure PCTCN2019091050-appb-000019
The synthesis steps are as follows:
Figure PCTCN2019091050-appb-000020
Figure PCTCN2019091050-appb-000020
首先在250mL二口瓶中加入
Figure PCTCN2019091050-appb-000021
(1.62g，5mmol)、吩恶嗪(2.20g，12mmol)、醋酸钯(90mg，0.4mmol)和三叔丁基膦四氟硼酸盐(0.34g，1.2mmol)，然后在手套箱中将NaOt-Bu(1.16g，12mmol)加入二口瓶中，并在氩气环境中下打入100mL不含水及氧的甲苯且在120℃反应24小时。当反应液冷却至室温后，将反应液倒入200mL冰水中，并以二氯甲烷萃取三次，合并有机相，干燥及旋干，再通过硅胶柱层析，其中二氯甲烷和正己烷的体积比是2:1，分离纯化，最后得到淡蓝色粉末1.6g，产物
Figure PCTCN2019091050-appb-000022
的产率是60％。产物鉴定数据： 1H NMR(300MHz,CD 2Cl 2,δ):8.11(s,2H),7.19-7.14(m,4H),7.05-6.96(m,12H),6.70(s,2H)。 First add it to a 250mL two-neck bottle
Figure PCTCN2019091050-appb-000021
(1.62g, 5mmol), phenoxazine (2.20g, 12mmol), palladium acetate (90mg, 0.4mmol) and tri-tert-butylphosphine tetrafluoroborate (0.34g, 1.2mmol), then put in a glove box NaOt-Bu (1.16 g, 12 mmol) was added to a two-neck flask, and 100 mL of toluene containing no water and oxygen was injected in an argon atmosphere and reacted at 120° C. for 24 hours. After the reaction solution was cooled to room temperature, the reaction solution was poured into 200 mL ice water and extracted three times with dichloromethane. The organic phases were combined, dried and spin-dried, and then passed through silica gel column chromatography. The volume of dichloromethane and n-hexane The ratio is 2:1, separated and purified, and finally 1.6g of light blue powder is obtained.
Figure PCTCN2019091050-appb-000022
The yield is 60%. Product identification data: 1 H NMR (300MHz, CD 2 Cl 2 , δ): 8.11 (s, 2H), 7.19-7.14 (m, 4H), 7.05-6.96 (m, 12H), 6.70 (s, 2H).
Figure PCTCN2019091050-appb-000023
的合成步骤如下所示：
Figure PCTCN2019091050-appb-000023
The synthesis steps are as follows:
Figure PCTCN2019091050-appb-000024
Figure PCTCN2019091050-appb-000024
首先在250mL二口瓶中加入
Figure PCTCN2019091050-appb-000025
(1.71g，5mmol)、吩恶嗪(2.20g，12mmol)、醋酸钯(90mg，0.4mmol)和三叔丁基膦四氟硼酸盐(0.34g，1.2mmol)，然后在手套箱中将NaOt-Bu(1.16g，12mmol)加入二口瓶中，并在氩气环境中下打入100mL不含水及氧的甲苯且在120℃反应24小时。当反应液冷却至室温后，将反应液倒入200mL冰水中，并以二氯甲烷萃取三次，合并有机相，干燥及旋干，再通过硅胶柱层析，其中二氯甲烷和正己烷的体积比是2:1，分离纯化，最后得到淡蓝色粉末1.5g，产物
Figure PCTCN2019091050-appb-000026
的产率是55％。产物鉴定数据： 1H NMR(300MHz,CD 2Cl 2,δ):8.12(s,2H),7.20-7.14(m,12H),6.96-6.89(m,2H),6.70(s,2H)。
Figure PCTCN2019091050-appb-000027
的合成步骤如下所示： First add it to a 250mL two-neck bottle
Figure PCTCN2019091050-appb-000025
(1.71g, 5mmol), phenoxazine (2.20g, 12mmol), palladium acetate (90mg, 0.4mmol) and tri-tert-butylphosphine tetrafluoroborate (0.34g, 1.2mmol), then put in a glove box NaOt-Bu (1.16 g, 12 mmol) was added to a two-neck flask, and 100 mL of toluene containing no water and oxygen was injected in an argon atmosphere and reacted at 120° C. for 24 hours. After the reaction solution was cooled to room temperature, the reaction solution was poured into 200 mL ice water and extracted three times with dichloromethane. The organic phases were combined, dried and spin-dried, and then passed through silica gel column chromatography. The volume of dichloromethane and n-hexane The ratio is 2:1, separated and purified, and finally 1.5g of light blue powder is obtained.
Figure PCTCN2019091050-appb-000026
The yield is 55%. Product identification data: 1 H NMR (300MHz, CD 2 Cl 2 , δ): 8.12 (s, 2H), 7.20-7.14 (m, 12H), 6.96-6.89 (m, 2H), 6.70 (s, 2H).
Figure PCTCN2019091050-appb-000027
The synthesis steps are as follows:
Figure PCTCN2019091050-appb-000028
Figure PCTCN2019091050-appb-000028
首先在250mL二口瓶中加入
Figure PCTCN2019091050-appb-000029
(1.76g，5mmol)、吩恶嗪(2.20g，12mmol)、醋酸钯(90mg，0.4mmol)和三叔丁基膦四氟硼酸盐(0.34g，1.2mmol)，然后在手套箱中将NaOt-Bu(1.16g，12mmol)加入二口瓶中，并在氩气环境中下打入100mL不含水及氧的甲苯且在120℃反应24小时。当反应液冷却至室温后，将反应液倒入200mL冰水中，并以二氯甲烷萃取三次，合并有机相，干燥及旋干，再通过硅胶柱层析，其中二氯甲烷和正己烷的体积比是2:1，分离纯化，最后得到淡蓝色粉末1.8g，产物
Figure PCTCN2019091050-appb-000030
的产率是65％。产物鉴定数据： 1H NMR(300MHz,CD 2Cl 2,δ):8.46(s,2H),7.20-7.14(m,4H),7.05-6.96(m,12H),6.71(s,2H),1.69(s,6H)。 First add it to a 250mL two-neck bottle
Figure PCTCN2019091050-appb-000029
(1.76g, 5mmol), phenoxazine (2.20g, 12mmol), palladium acetate (90mg, 0.4mmol) and tri-tert-butylphosphine tetrafluoroborate (0.34g, 1.2mmol), then put in a glove box NaOt-Bu (1.16 g, 12 mmol) was added to a two-neck flask, and 100 mL of toluene containing no water and oxygen was injected in an argon atmosphere and reacted at 120° C. for 24 hours. After the reaction solution was cooled to room temperature, the reaction solution was poured into 200 mL ice water and extracted three times with dichloromethane. The organic phases were combined, dried and spin-dried, and then passed through silica gel column chromatography. The volume of dichloromethane and n-hexane The ratio is 2:1, separated and purified, and finally 1.8g of light blue powder is obtained.
Figure PCTCN2019091050-appb-000030
The yield is 65%. Product identification data: 1 H NMR (300MHz, CD 2 Cl 2 , δ): 8.46 (s, 2H), 7.20-7.14 (m, 4H), 7.05-6.96 (m, 12H), 6.71 (s, 2H), 1.69 (s, 6H).
参考图1，图1是本发明实施例的
Figure PCTCN2019091050-appb-000031
的最高电子占据轨道(HOMO)与最低电子未占据轨道(LUMO)分布图。 Refer to Figure 1, which is an example of the present invention
Figure PCTCN2019091050-appb-000031
The highest electron occupied orbital (HOMO) and lowest electron unoccupied orbital (LUMO) distribution diagrams of.
Figure PCTCN2019091050-appb-000032
的最低单重态(S1)、最低三重态能级(T1)和电化学能级如下表1所示：
Figure PCTCN2019091050-appb-000032
The lowest singlet state (S1), lowest triplet energy level (T1) and electrochemical energy levels of are shown in Table 1:
Figure PCTCN2019091050-appb-000033
Figure PCTCN2019091050-appb-000033
表1Table 1
参考图2，图2是本发明实施例的
Figure PCTCN2019091050-appb-000034
的最高电子占据轨道(HOMO)与最低电子未占据轨道(LUMO)分布图。 Refer to Figure 2, which is an example of the present invention
Figure PCTCN2019091050-appb-000034
The highest electron occupied orbital (HOMO) and lowest electron unoccupied orbital (LUMO) distribution diagrams of.
Figure PCTCN2019091050-appb-000035
的最低单重态(S1)和最低三重态能级(T1)，电化学能级如下表2所示：
Figure PCTCN2019091050-appb-000035
The lowest singlet state (S1) and lowest triplet energy level (T1) of, the electrochemical energy levels are shown in Table 2 below:
PL PeakPL Peak S 1 S 1 T 1 T 1 ΔE ST ΔE ST HOMOHOMO LUMOLUMO
(nm)(nm) (eV)(eV) (eV)(eV) (eV)(eV) (eV)(eV) (eV)(eV)
497497 2.502.50 2.432.43 0.070.07 -5.46-5.46 -2.43-2.43
表2Table 2
参考图3，图3是本发明实施例的
Figure PCTCN2019091050-appb-000036
的最高电子占据轨道(HOMO)与最低电子未占据轨道(LUMO)分布图。 Referring to Figure 3, Figure 3 is an embodiment of the present invention
Figure PCTCN2019091050-appb-000036
The highest electron occupied orbital (HOMO) and lowest electron unoccupied orbital (LUMO) distribution diagrams of.
Figure PCTCN2019091050-appb-000037
的最低单重态(S1)和最低三重态能级(T1)，电化学能级如下表3所示：
Figure PCTCN2019091050-appb-000037
The lowest singlet state (S1) and lowest triplet energy level (T1), the electrochemical energy levels are shown in Table 3:
Figure PCTCN2019091050-appb-000038
Figure PCTCN2019091050-appb-000038
表3table 3
参考图4，图4是本发明实施例的热活化延迟荧光材料(化合物I、化合物II及化合物II)在甲苯溶液中的光致发光光谱。Referring to FIG. 4, FIG. 4 is a photoluminescence spectrum of thermally activated delayed fluorescent materials (compound I, compound II, and compound II) in a toluene solution according to an embodiment of the present invention.
本发明另一实施例提供一种有机发光二极管显示设备，包括阳极、阴极以及位于阳极与阴极之间的有机功能层，有机功能层包括热活化延迟荧光材料，热活化延迟荧光材料包括如下所示的结构:Another embodiment of the present invention provides an organic light emitting diode display device, including an anode, a cathode, and an organic functional layer located between the anode and the cathode. The organic functional layer includes a thermally activated delayed fluorescent material. The thermally activated delayed fluorescent material includes the following Structure:
Figure PCTCN2019091050-appb-000039
Figure PCTCN2019091050-appb-000039
具体而言，具有上述化学结构的热活化延迟荧光材料在有机发光二极管显示设备中可以作为荧光主体材料或电子传输材料。Specifically, the thermally activated delayed fluorescent material having the above chemical structure can be used as a fluorescent host material or an electron transporting material in an organic light emitting diode display device.
参考图5，本发明实施例的热活化延迟荧光材料作为发光层的有机发光二极管显示设备包括玻璃和导电玻璃(ITO)层10、空穴注入层20、空穴传输层30、发光层40、电子传输层50及阴极层60。另外，有机发光二极管显示设备可按本发明技术领域已知的方法完成，故不再赘述。5, an organic light emitting diode display device with a thermally activated delayed fluorescent material as a light emitting layer of an embodiment of the present invention includes a glass and conductive glass (ITO) layer 10, a hole injection layer 20, a hole transport layer 30, a light emitting layer 40, Electron transport layer 50 and cathode layer 60. In addition, the organic light emitting diode display device can be completed according to the method known in the technical field of the present invention, so it will not be repeated.
有机发光二极管显示设备的电流、亮度及电压特性是由带有校正过的硅光电二极管的Keithley源测量系统(Keithley 2400 Sourcemeter、Keithley 2000 Currentmeter)完成的，电致发光光谱是由法国JY公司SPEX CCD3000光谱仪测量的，所有测量均在正常大气压及室温中完成。The current, brightness and voltage characteristics of the organic light-emitting diode display device are completed by the Keithley source measurement system (Keithley 2400 Sourcemeter, Keithley 2000 Currentmeter) with a calibrated silicon photodiode. The electroluminescence spectrum is performed by the French JY company SPEX CCD3000 All measurements measured by the spectrometer are done under normal atmospheric pressure and room temperature.
有机发光二极管显示设备(I、II及III)分别使用含有
Figure PCTCN2019091050-appb-000040
及
Figure PCTCN2019091050-appb-000041
热活化延迟荧光材料的性能数据如下表4所示： Organic light-emitting diode display devices (I, II and III) are used containing
Figure PCTCN2019091050-appb-000040
and
Figure PCTCN2019091050-appb-000041
The performance data of thermally activated delayed fluorescent materials are shown in Table 4 below:
Figure PCTCN2019091050-appb-000042
Figure PCTCN2019091050-appb-000042
表4Table 4
本发明的热活化延迟荧光材料具有较低的最低单三重态的能级差、高反 向系间窜越常数及高的光致发光量子产率的性质，进而实现具有高发光效率的有机发光二极管显示设备。The thermally activated delayed fluorescent material of the present invention has the properties of low energy level difference of the lowest single triplet state, high reverse system crossover constant and high photoluminescence quantum yield, thereby realizing an organic light emitting diode with high luminous efficiency display screen.
虽然本发明结合其具体实施例而被描述，应该理解的是，许多替代、修改及变化对于那些本领域的技术人员将是显而易见的。因此，其意在包含落入所附权利要求书的范围内的所有替代、修改及变化。Although the present invention has been described in conjunction with its specific embodiments, it should be understood that many alternatives, modifications and changes will be apparent to those skilled in the art. Therefore, it is intended to include all substitutions, modifications and changes that fall within the scope of the appended claims.

Claims (14)

  1. 一种热活化延迟荧光材料，包括如式(I)所示的结构:A thermally activated delayed fluorescent material includes the structure shown in formula (I):
    Figure PCTCN2019091050-appb-100001
    Figure PCTCN2019091050-appb-100001
    其中，R选自氧、硫或C1-C3的烷基。Wherein, R is selected from oxygen, sulfur or C1-C3 alkyl.
  2. 如权利要求1所述的热活化延迟荧光材料，其中，所述热活化延迟荧光材料如下所示：The thermally activated delayed fluorescent material of claim 1, wherein the thermally activated delayed fluorescent material is as follows:
    Figure PCTCN2019091050-appb-100002
    Figure PCTCN2019091050-appb-100002
  3. 如权利要求1所述的热活化延迟荧光材料，其中，所述热活化延迟荧光材料如下所示：The thermally activated delayed fluorescent material of claim 1, wherein the thermally activated delayed fluorescent material is as follows:
    Figure PCTCN2019091050-appb-100003
    Figure PCTCN2019091050-appb-100003
  4. 如权利要求1所述的热活化延迟荧光材料，其中，所述热活化延迟荧光材料如下所示：The thermally activated delayed fluorescent material of claim 1, wherein the thermally activated delayed fluorescent material is as follows:
    Figure PCTCN2019091050-appb-100004
    Figure PCTCN2019091050-appb-100004
  5. 一种有机发光二极管显示设备，包括阳极、阴极以及位于所述阳极与所述阴极之间的有机功能层，所述有机功能层包括热活化延迟荧光材料，所述热活化延迟荧光材料包括如式(I)所示的结构:An organic light emitting diode display device includes an anode, a cathode, and an organic functional layer located between the anode and the cathode. The organic functional layer includes a thermally activated delayed fluorescent material, and the thermally activated delayed fluorescent material includes the formula (I) The structure shown:
    Figure PCTCN2019091050-appb-100005
    Figure PCTCN2019091050-appb-100005
    其中，R选自氧、硫或C1-C3的烷基。Wherein, R is selected from oxygen, sulfur or C1-C3 alkyl.
  6. 如权利要求5所述的有机发光二极管显示设备，其中，所述热活化延迟荧光材料如下所示：8. The organic light emitting diode display device of claim 5, wherein the thermally activated delayed fluorescent material is as follows:
    Figure PCTCN2019091050-appb-100006
    Figure PCTCN2019091050-appb-100006
  7. 如权利要求5所述的有机发光二极管显示设备，其中，所述热活化延迟荧光材料如下所示：8. The organic light emitting diode display device of claim 5, wherein the thermally activated delayed fluorescent material is as follows:
    Figure PCTCN2019091050-appb-100007
    Figure PCTCN2019091050-appb-100007
  8. 如权利要求5所述的有机发光二极管显示设备，其中，所述热活化延迟荧光材料如下所示：8. The organic light emitting diode display device of claim 5, wherein the thermally activated delayed fluorescent material is as follows:
    Figure PCTCN2019091050-appb-100008
    Figure PCTCN2019091050-appb-100008
  9. 如权利要求5所述的有机发光二极管显示设备，其中，所述热活化延迟荧光材料在所述有机发光二极管显示设备中作为荧光主体材料。5. The organic light emitting diode display device of claim 5, wherein the thermally activated delayed fluorescent material is used as a fluorescent host material in the organic light emitting diode display device.
  10. 如权利要求5所述的有机发光二极管显示设备，其中，所述热活化延迟荧光材料在所述有机发光二极管显示设备中作为电子传输材料。5. The organic light emitting diode display device of claim 5, wherein the thermally activated delayed fluorescent material is used as an electron transport material in the organic light emitting diode display device.
  11. 一种有机发光二极管显示设备，包括阳极、阴极以及位于所述阳极与所述阴极之间的有机功能层，所述有机功能层包括热活化延迟荧光材料，所述 热活化延迟荧光材料包括如式(I)所示的结构:An organic light emitting diode display device includes an anode, a cathode, and an organic functional layer located between the anode and the cathode. The organic functional layer includes a thermally activated delayed fluorescent material, and the thermally activated delayed fluorescent material includes the formula (I) The structure shown:
    Figure PCTCN2019091050-appb-100009
    Figure PCTCN2019091050-appb-100009
    其中，R选自氧、硫或C1-C3的烷基，所述热活化延迟荧光材料在所述有机发光二极管显示设备中作为荧光主体材料和电子传输材料。Wherein, R is selected from oxygen, sulfur or C1-C3 alkyl, and the thermally activated delayed fluorescent material is used as a fluorescent host material and an electron transport material in the organic light emitting diode display device.
  12. 如权利要求11所述的有机发光二极管显示设备，其中，所述热活化延迟荧光材料如下所示：11. The organic light emitting diode display device of claim 11, wherein the thermally activated delayed fluorescent material is as follows:
    Figure PCTCN2019091050-appb-100010
    Figure PCTCN2019091050-appb-100010
  13. 如权利要求11所述的有机发光二极管显示设备，其中，所述热活化延迟荧光材料如下所示：11. The organic light emitting diode display device of claim 11, wherein the thermally activated delayed fluorescent material is as follows:
    Figure PCTCN2019091050-appb-100011
    Figure PCTCN2019091050-appb-100011
  14. 如权利要求11所述的有机发光二极管显示设备，其中，所述热活化延迟荧光材料如下所示：11. The organic light emitting diode display device of claim 11, wherein the thermally activated delayed fluorescent material is as follows:
    Figure PCTCN2019091050-appb-100012
    Figure PCTCN2019091050-appb-100012
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