WO2020082568A1 - 吖啶衍生物及有机电致发光器件 - Google Patents

吖啶衍生物及有机电致发光器件 Download PDF

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WO2020082568A1
WO2020082568A1 PCT/CN2018/123251 CN2018123251W WO2020082568A1 WO 2020082568 A1 WO2020082568 A1 WO 2020082568A1 CN 2018123251 W CN2018123251 W CN 2018123251W WO 2020082568 A1 WO2020082568 A1 WO 2020082568A1
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acridine derivative
organic light
electron donor
electrode
formula
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罗佳佳
顾宇
黄金昌
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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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    • H10K50/17—Carrier injection layers

Definitions

  • the present application relates to the technical field of organic electroluminescence, in particular to an acridine derivative, and an organic electroluminescence device and a display panel using the acridine derivative.
  • Organic light-emitting diodes (organic light-emitting diodes, OLEDs) with their active light do not require a backlight, high luminous efficiency, large viewing angle, fast response, large temperature adaptation range, relatively simple production and processing technology, low driving voltage
  • OLEDs organic light-emitting diodes
  • the luminescent guest material that plays a leading role is crucial.
  • the luminescent guest materials used in early OLEDs were fluorescent materials. Since the ratio of singlet and triplet excitons in OLED is 1: 3, the theoretical internal quantum efficiency (IQE) of OLEDs based on fluorescent materials can only reach 25% , which greatly limits the application of fluorescent electroluminescent devices.
  • Heavy metal complex phosphorescent materials can achieve 100% IQE by utilizing singlet and triplet excitons simultaneously due to the spin-orbit coupling of heavy atoms.
  • the heavy metals commonly used are precious metals such as Ir and Pt, and the phosphorescent luminescent materials of the heavy metal complexes have yet to be broken through in terms of blue materials.
  • TADF organic thermally activated delayed fluorescence
  • RISC reverse intersystem crossing
  • TADF materials For TADF materials, fast reverse intersystem crossing constant (k RISC ) and high photoluminescence quantum yield (PLQY) are necessary conditions for the preparation of high-efficiency OLEDs. At present, TADF materials with the above conditions are still relatively scarce compared to heavy metal Ir complexes. In the field of deep blue light where phosphorescent heavy metal materials need to be broken through, TADF materials are rare.
  • k RISC fast reverse intersystem crossing constant
  • PLQY photoluminescence quantum yield
  • the acridine derivatives described in this application through clever molecular design, a series of compounds with high single and triplet energy levels have been synthesized.
  • the acridine derivative can be used as a deep blue fluorescent material, and further applied to the organic light-emitting layer of an organic electroluminescent device to obtain a series of high-performance OLEDs.
  • D represents an electron donor unit
  • the electron donor unit contains an acridine structure
  • the electron donor unit has a structure represented by formula (I-2), (I-3) or (I-4):
  • R 2 and R 1 or R 3 are connected to form an aromatic ring; or, R 3 and R 4 are connected to form an aromatic ring;
  • Ar is a substituted or unsubstituted aromatic hydrocarbon group.
  • the electron donor unit when R 2 and R 1 or R 3 are connected to form an aromatic ring, the electron donor unit has a structure represented by formula (I-2-a) or (I-2-b) :
  • the electron donor unit has a structure represented by formula (I-2-c):
  • the Ar represents a benzene ring.
  • the electron donor unit has formulas (I-3-a), (I-3-b), (I-3-c), (I-4-a), (I-4 -b) or (I-4-c):
  • the acridine derivative has the structure shown in compounds 1 to 3:
  • the present application also provides an organic electroluminescent device including a first electrode, a second electrode, and at least one organic light-emitting layer disposed between the first electrode and the second electrode, wherein the organic light-emitting layer Contains a fluorescent material selected from the acridine derivatives described above.
  • the organic light emitting diode device further includes: a hole injection layer disposed between the first electrode and the organic light emitting layer, and disposed between the hole injection layer and the organic light emitting layer A hole transport layer in between, and an electron transport layer disposed between the organic light emitting layer and the second electrode.
  • the present application also provides a display panel including the above organic electroluminescent device.
  • FIG. 1 is an orbital distribution diagram of the compounds 1 to 3 described in Examples 1 to 3 of the present invention.
  • FIG. 4 is a schematic structural view of an organic electroluminescent device according to an embodiment of the invention.
  • FIG. 5 is a schematic structural diagram of a display panel according to an embodiment of the invention.
  • the first feature “above” or “below” the second feature may include the first and second features in direct contact, or may include the first and second features Contact not directly but through other features between them.
  • the first feature is “above”, “above” and “above” the second feature includes that the first feature is directly above and obliquely above the second feature, or simply means that the first feature is higher in level than the second feature.
  • the first feature is “below”, “below” and “below” the second feature includes that the first feature is directly below and obliquely below the second feature, or simply means that the first feature is less horizontal than the second feature.
  • an acridine derivative which has the structure shown in compound 1:
  • the synthetic route of the compound 1 is as follows:
  • reaction liquid was poured into 50 mL of ice water and extracted three times with dichloromethane.
  • the organic phases obtained by extraction were combined, spinned into silica gel, and separated and purified by column chromatography (dichloromethane: n-hexane, v: v, 3: 1) to obtain 2.0 g of blue-white powder with a yield of 85%.
  • an acridine derivative is provided, which has the structure shown in compound 2:
  • the synthetic route of the compound 2 is as follows:
  • reaction liquid was poured into 50 mL of ice water, and extracted three times with dichloromethane.
  • the organic phases obtained by extraction were combined, spinned into silica gel, and purified by column chromatography (dichloromethane: n-hexane, v: v, 3: 1) to obtain 1.7 g of blue-white powder with a yield of 72%.
  • an acridine derivative is provided, which has the structure shown in compound 3:
  • the synthetic route of the compound 3 is as follows:
  • reaction liquid was poured into 50 mL of ice water, and extracted three times with dichloromethane.
  • the organic phases obtained by extraction were combined, spinned into silica gel, and purified by column chromatography (dichloromethane: n-hexane, v: v, 3: 1) to obtain 1.1 g of blue-white powder with a yield of 47%.
  • FIG. 1 shows the orbit distribution diagrams of the above compounds 1 to 3; showing the distribution of the highest electron occupied orbit (HOMO) and lowest electron unoccupied orbit (LUMO) electron cloud of compounds 1 to 3, respectively.
  • HOMO highest electron occupied orbit
  • LUMO lowest electron unoccupied orbit
  • the above experimental data shows that the target compound has a very high triplet energy level and is suitable for use as a blue dopant material in OLEDs.
  • an organic electroluminescent device is provided.
  • the organic electroluminescent device 100 includes a first electrode 11, a hole injection layer 12, a hole transport layer 13, an organic light-emitting layer 14, an electron transport layer 15, and a second electrode 16 in this order.
  • the organic light-emitting layer 14 includes a dark blue thermally activated delayed fluorescent material, and the dark blue thermally activated delayed fluorescent material is at least one of the compounds 1 to 3.
  • the organic electroluminescent device 100 shown in FIG. 4 is only an example, and those skilled in the art can increase or decrease part of the functional layer according to actual process requirements, for example, in the electronic transmission
  • An electron injection layer 17 can also be provided between the layer 15 and the second electrode 16.
  • the above-mentioned layers are formed by using conventional materials in the art using conventional materials in the art.
  • the first electrode 11 is an anode, which may be made of indium tin metal oxide (ITO).
  • ITO indium tin metal oxide
  • the hole injection layer 12 may be made of poly (3,4-ethylenedioxythiophene) -polystyrenesulfonic acid (PEDOT: PSS), polythiophene, or polyaniline.
  • PEDOT polystyrenesulfonic acid
  • polythiophene polythiophene
  • polyaniline polyaniline
  • the hole transport layer 13 may be made of an aromatic diamine-based compound, a triphenylamine compound, an aromatic triamine-based compound, a biphenyldiamine derivative, a triarylamine polymer, or a carbazole-based polymer.
  • the organic light-emitting layer 14 is composed of bis [2-((oxo) diphenylphosphino) phenyl] ether (DPEPO) as a light-emitting host, and is doped with at least one of the compounds 1 to 3.
  • DPEPO bis [2-((oxo) diphenylphosphino) phenyl] ether
  • the electron transport layer 15 may be made of 1,3,5-tris (3- (3-pyridyl) phenyl) benzene (Tm3PyPB).
  • the second electrode 16 is a cathode, and may be made of Al or Mg / Ag.
  • the electron injection layer 17 may be made of LiF.
  • the specific manufacturing method of the organic electroluminescent device 100 is: spin coating PESOT: PSS on the cleaned ITO substrate, and then sequentially depositing TmPyPB, LiF and Al under high vacuum conditions.
  • the organic electroluminescent device containing the compound 1 in the organic light-emitting layer 14 is referred to as device A, and the organic electroluminescent device containing the compound 2 in the organic light-emitting layer 14 is referred to as It is device B, and the organic electroluminescence device containing the compound 3 in the organic light-emitting layer 14 is referred to as device C.
  • the specific structures of the device A, device B, and device C are as follows:
  • ITO / PEDOT PSS (50nm) / DPEPO: Compound 1 (3% 40nm) / TmPyPB (40nm) / LiF (1nm) / Al (100nm);
  • ITO / PEDOT PSS (50nm) / DPEPO: Compound 2 (5% 40nm) / TmPyPB (40nm) / LiF (1nm) / Al (100nm);
  • ITO / PEDOT PSS (50 nm) / DPEPO: Compound 3 (5% 40 nm) / TmPyPB (40 nm) / LiF (1 nm) / Al (100 nm).
  • the electroluminescence spectra of the above device A, device B and device C were measured with SPEX CCD3000 spectrometer of French JY company, and the performance data shown in Table 2 was obtained through calculation.
  • the current-luminance-voltage characteristics of the above-mentioned device A, device B and device C can also be detected with a Keithley source measurement system (Keithley 2400 Sourcemeter, Keithley 2000 Currentmeter).
  • the display panel 200 includes a substrate 21 on which a plurality of organic electroluminescent devices 100 are formed.
  • the organic electroluminescent device 100 may be the device A, the device B or the device C.
  • the substrate 21 may also be formed with a structure that has undergone several previous steps, for example, there may be an inorganic film layer, several film layers in the thin film transistor structure, or a complete thin film transistor has been formed line.
  • the display panel 200 also includes other known structures such as package covers, which will not be repeated here.
  • the purpose of reducing the lowest single and triple energy level difference and high energy level of the target molecule is achieved.
  • a series of compounds with high singlet triplet energy levels and excellent luminescent properties have been developed. These compounds can be included in the organic light-emitting layer as a fluorescent material, especially as a deep blue thermally activated delayed fluorescent material, thereby making a series of high-performance electrothermally activated delayed fluorescent devices.
  • the subject of this application can be manufactured and used in industry and has industrial applicability.

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Abstract

本申请提供一种吖啶衍生物，具有式(I)所示结构。该吖啶衍生物可以作为荧光材料，尤其是作为深蓝色热激活延迟荧光材料而包含于有机发光层，从而制成一系列高性能的电致热激活延迟荧光器件。

Description

吖啶衍生物及有机电致发光器件 技术领域
本申请涉及有机电致发光技术领域，特别涉及一种吖啶衍生物，以及应用该吖啶衍生物的有机电致发光器件及显示面板。
背景技术
有机电致发光二极管(organic light-emitting diodes，OLEDs)以其主动发光不需要背光源、发光效率高、可视角度大、响应速度快、温度适应范围大、生产加工工艺相对简单、驱动电压低，能耗小，更轻更薄，柔性显示等优点以及巨大的应用前景，吸引了众多研究者的关注。
在OLED中，起主导作用的发光客体材料至关重要。早期的OLED使用的发光客体材料为荧光材料，由于在OLED中单重态和三重态的激子比例为1:3，因此基于荧光材料的OLED的理论内量子效率(IQE)只能达到25％，极大的限制了荧光电致发光器件的应用。
重金属配合物磷光材料由于重原子的自旋轨道耦合作用，使得它能够同时利用单重态和三重态激子而实现100％的IQE。然而，通常使用的重金属都是Ir、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尚有待突破。
纯有机热活化延迟荧光(TADF)材料，通过巧妙的分子设计，使得分子具有较小的最低单三重能级差(ΔE ST)，这样三重态激子可以通过反向系间窜越(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、三重态激子，也可以实现100％的IQE。
技术问题
对于TADF材料，快速的反向系间窜越常数(k RISC)以及高的光致发光量子产率(PLQY)是制备高效率OLED的必要条件。目前，具备上述条件的TADF材料相对于重金属Ir配合物而言还是比较匮乏，在磷光重金属材料有待突破的深蓝光领域，TADF材料方面更是寥寥无几。
据此，需要开发新的荧光材料，以解决深蓝光领域的技术空白。
技术解决方案
在根据本申请所述的吖啶衍生物，通过巧妙的分子设计，合成了一系列具有高的单三线态能级的化合物。该吖啶衍生物可以用作深蓝光荧光材料，并进而应用于有机电致发光器件的有机发光层，以获得一系列高性能的OLED。
为了达到上述目的，提供一种吖啶衍生物，具有式(I)所示结构：
Figure PCTCN2018123251-appb-000001
其中，D代表电子给体单元，所述电子给体单元含有吖啶结构。
在一实施例中，所述电子给体单元具有式(I-2)、(I-3)或(I-4)所示的结构：
Figure PCTCN2018123251-appb-000002
其中，R 2与R 1或R 3连接形成芳环；或者，R 3与R 4连接形成芳环；
并且，Ar为取代或非取代的芳烃基团。
在一实施例中，当所述R 2与R 1或R 3连接形成芳环时，所述电子给体单元具有式(I-2-a)或(I-2-b)所示的结构：
Figure PCTCN2018123251-appb-000003
当所述R 3与R 4连接形成芳环时，所述电子给体单元具有式(I-2-c)所示的结构：
Figure PCTCN2018123251-appb-000004
在一实施例中，所述Ar代表苯环。
在一实施例中，所述电子给体单元具有式(I-3-a)、(I-3-b)、(I-3-c)、(I-4-a)、(I-4-b)或(I-4-c)所示的结构：
Figure PCTCN2018123251-appb-000005
在一实施例中，所述吖啶衍生物具有化合物1～3所示的结构：
Figure PCTCN2018123251-appb-000006
本申请还提供一种有机电致发光器件，包括第一电极、第二电极及设置于所述第一电极与所述第二电极之间的至少一有机发光层，其中，所述有机发光层包含荧光材料，所述荧光材料选自上述吖啶衍生物。
在一实施例中，所述有机发光二极管器件还包括：设置于所述第一电极与所述有机发光层之间的一空穴注入层，设置于所述空穴注入层与所述有机发光层之间的一空穴传输层，以及，设置于所述有机发光层与所述第二电极之间的一电子传输层。
本申请还提供一种显示面板，包括上述有机电致发光器件。
有益效果
在本申请中，通过筛选不同的电子给体单元并调节电子给体与电子受体之间的扭转角及电荷转移特性，达到减小目标分子最低单三重能级差以及高能级的目的，进而合成了一 系列具有高单三线态能级、优良发光性能的化合物。该些化合物可以作为荧光材料，尤其是作为深蓝色热激活延迟荧光材料而包含于有机发光层，从而制成一系列高性能的电致热激活延迟荧光器件。
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是本发明实施例1～3中所述化合物1～3的轨道分布图；
图2是室温下甲苯溶液中本发明所述化合物1～3的光致发光光谱；
图3是室温下甲苯溶液中本发明化合物1～3的瞬态光致发光光谱；
图4是根据本发明一实施例的有机电致发光器件的结构示意图；
图5是根据本发明一实施例的显示面板的结构示意图。
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。
在本发明中，除非另有明确的规定和限定，第一特征在第二特征之“上”或之“下”可以包括第一和第二特征直接接触，也可以包括第一和第二特征不是直接接触而是通过它们之间的另外的特征接触。而且，第一特征在第二特征“之上”、“上方”和“上面”包括第一特征在第二特征正上方和斜上方，或仅仅表示第一特征水平高度高于第二特征。第一特征在第二特征“之下”、“下方”和“下面”包括第一特征在第二特征正下方和斜下方，或仅仅表示第一特征水平高度小于第二特征。
下文的公开提供了许多不同的实施方式或例子用来实现本发明的不同结构。为了简化本发明的公开，下文中对特定例子的部件和设置进行描述。当然，它们仅仅为示例，并且目的不在于限制本发明。此外，本发明可以在不同例子中重复参考数字和/或参考字母，这种重复是为了简化和清楚的目的，其本身不指示所讨论各种实施方式和/或设置之间的关系。此外，本发明提供了的各种特定的工艺和材料的例子，但是本领域普通技术人员可以意识到其他工艺的应用和/或其他材料的使用。
实施例1.化合物1的制备
在本实施例中，提供一种吖啶衍生物，具有化合物1所示的结构：
Figure PCTCN2018123251-appb-000007
所述化合物1的合成路线如下所示：
Figure PCTCN2018123251-appb-000008
具体合成步骤如下：
1.向100mL二口瓶中加入原料1(1.45g，5mmol)、原料2(1.55g，6mmol)、醋酸钯(45mg，0.2mmol)和三叔丁基膦四氟硼酸盐(0.17g，0.6mmol)。然后，将所述二口瓶移入密闭环境中，并加入NaOt-Bu(0.58g，6mmol)。接着，在氩气氛围下打入40mL事先除水除氧的甲苯，于120℃反应48小时；
2.待反应液冷却至室温后，将反应液倒入50mL冰水中，以二氯甲烷萃取三次。合并萃取获得的有机相，旋成硅胶，柱层析(二氯甲烷:正己烷，v:v，3:1)分离纯化，得蓝白色粉末2.0g，产率85％。 1H NMR(300MHz,CD 2Cl 2,δ):7.79(d,J＝6.9Hz,1H),7.70(d,J＝6.6Hz,1H),7.43-7.28(m,6H),7.20-7.14(m,4H),6.93-6.87(m,3H),6.20(d,J＝6.6Hz,1H),5.67(s,1H),1.75(s,6H).MS(EI)m/z:[M] +calcd for C 31H 23N 2OP,470.15；found,470.09.Anal.Calcd for 470.15:C 79.14,H 4.93,N 5.95；found:C 79.07,H 5.07,N 5.82.
实施例2.化合物2的制备
在本实施例中，提供一种吖啶衍生物，具有化合物2所示的结构：
Figure PCTCN2018123251-appb-000009
所述化合物2的合成路线如下所示：
Figure PCTCN2018123251-appb-000010
具体合成步骤如下：
1.向100mL二口瓶中加入原料1(1.45g，5mmol)、原料3(1.55g，6mmol)、醋酸钯(45mg，0.2mmol)和三叔丁基膦四氟硼酸盐(0.17g，0.6mmol)。然后，将所述二口瓶移入密闭环境中，并加入NaOt-Bu(0.58g，6mmol)。接着，在氩气氛围下打入40mL事先除水除氧的甲苯，于120℃反应48小时；
2.待反应液冷却至室温后，将反应液倒入50mL冰水中，以二氯甲烷萃取三次。合并萃取获得的有机相，旋成硅胶，柱层析(二氯甲烷:正己烷，v:v，3:1)分离纯化，得蓝白色粉末1.7g，产率72％。 1H NMR(300MHz,CD 2Cl 2,δ):7.96(d,J＝6.6Hz,1H),7.88(d,J＝6.0Hz,1H),7.79(d,J＝6.3Hz,1H),7.61-7.50(m,4H),7.48-7.37(m,4H),7.27-7.00(m,4H),6.20(d,J＝6.6Hz,1H),5.67(s,1H),1.82(s,6H).MS(EI)m/z:[M] +calcd for C 31H 23N 2OP,470.15；found,470.13.Anal.Calcd for 470.15:C 79.14,H 4.93,N 5.95；found:C 79.00,H 4.87,N 5.89.
实施例3.化合物3的制备
在本实施例中，提供一种吖啶衍生物，具有化合物3所示的结构：
Figure PCTCN2018123251-appb-000011
所述化合物3的合成路线如下所示：
Figure PCTCN2018123251-appb-000012
具体合成步骤如下：
1.向100mL二口瓶中加入原料1(1.45g，5mmol)、原料4(1.55g，6mmol)、醋酸钯(45mg，0.2mmol)和三叔丁基膦四氟硼酸盐(0.17g，0.6mmol)。然后，将所述二口瓶移入密闭环境中，并加入NaOt-Bu(0.58g，6mmol)。接着，在氩气氛围下打入40mL事先除水除氧的甲苯，于120℃反应48小时；
2.待反应液冷却至室温后，将反应液倒入50mL冰水中，以二氯甲烷萃取三次。合并萃取获得的有机相，旋成硅胶，柱层析(二氯甲烷:正己烷，v:v，3:1)分离纯化，得蓝白色粉末1.1g，产率47％。 1H NMR(300MHz,CD 2Cl 2,δ):8.13(d,J＝6.9Hz,1H),8.06(d,J＝6.6Hz,1H),7.69(d,J＝6.9Hz,1H),7.49-7.40(m,3H),7.36-7.17(m,9H),6.20(d,J＝6.6Hz,1H),5.67(s,1H),1.75(s,6H).MS(EI)m/z:[M] +calcd for C 31H 23N 2OP,470.15；found,470.11.Anal.Calcd for 470.15:C 79.14,H 4.93,N 5.95；found:C 79.11,H 5.00,N 5.76.
实施例4.化合物1～3的检测和实验验证
在本实施例中，对实施例1～3中获得的化合物1～3进行检测和实验验证。
请参见图1，图1所示的是上述化合物1～3的轨道分布图；分别显示了化合物1～3的最高电子占据轨道(HOMO)与最低电子未占据轨道(LUMO)电子云分布。
经理论模拟计算，获得表1所示的上述化合物1～3的最低单重态(S1)、最低三重态能级(T1)及电化学能级。
表1.化合物1～3的最低单重态(S1)、最低三重态能级(T1)及电化学能级
  PL Peak(nm) S 1(eV) T 1(eV) ΔE ST(eV) HOMO(eV) LUMO(eV)
化合物1 422 2.94 2.87 0.07 -5.48 -2.00
化合物2 427 2.91 2.80 0.11 -5.65 -2.00
化合物3 464 2.67 2.32 0.35 -5.22 -2.00
此外，在本实施例中，进一步对上述化合物1～3的光物理性质进行实验验证，获得如图2所示的室温下甲苯溶液中化合物1～3的光致发光光谱，以及，如图3所示的室温下甲苯溶液中化合物1～3的瞬态光致发光光谱。
由上述实验数据表明：目标化合物具有非常高的三线态能级，适合作为蓝光掺杂剂材料应用于OLED中。
实施例5.有机电致发光器件
在本实施例中，提供一有机电致发光器件。如图4所示，所述有机电致发光器件100依次包括：第一电极11、空穴注入层12、空穴传输层13、有机发光层14、电子传输层 15，以及第二电极16。其中，所述有机发光层14中包含深蓝色热激活延迟荧光材料，所述深蓝色热激活延迟荧光材料为所述化合物1～3中的至少一种。
本领域技术人员可以理解的是，图4所示的所述有机电致发光器件100仅作为一范例，本领域技术人员可以根据实际工艺要求增加或减少部分功能层，例如，在所述电子传输层15与所述第二电极16之间还可以设置一电子注入层17。并且，上述各层均以本领域常规材料通过本领域常规工艺形。
例如，所述第一电极11为阳极，可以采用铟锡金属氧化物(ITO)制成。
例如，所述空穴注入层12可以采用聚(3,4-乙烯二氧噻吩)-聚苯乙烯磺酸(PEDOT:PSS)、聚噻吩或聚苯胺制成。
例如，所述空穴传输层13可以采用芳香族二胺类化合物、三苯胺化合物、芳香族三胺类化合物、联苯二胺衍生物、三芳胺聚合物或咔唑类聚合物制成。
例如，所述有机发光层14由二[2-((氧代)二苯基膦基)苯基]醚(DPEPO)为发光主体，掺杂所述化合物1～3中的至少一种。
例如，所述电子传输层15可以采用1,3,5-三(3-(3-吡啶基)苯基)苯(Tm3PyPB)制成。
例如，所述第二电极16为阴极，可以采用Al或Mg/Ag制成。
例如，所述电子注入层17可以采用LiF制成。
例如，所述有机电致发光器件100的具体制作方法为：在经过清洗的ITO衬底上旋涂PESOT:PSS，然后在高真空条件下依次蒸镀TmPyPB、LiF和Al。
在本实施例中，将所述有机发光层14中包含所述化合物1的有机电致发光器件记为器件A，将所述有机发光层14中包含所述化合物2的有机电致发光器件记为器件B，并将所述有机发光层14中包含所述化合物3的有机电致发光器件记为器件C。
作为一具体实施例，所述器件A、器件B和器件C的具体结构如下：
器件A：ITO/PEDOT:PSS(50nm)/DPEPO:化合物1(3％40nm)/TmPyPB(40nm)/LiF(1nm)/Al(100nm)；
器件B：ITO/PEDOT:PSS(50nm)/DPEPO:化合物2(5％40nm)/TmPyPB(40nm)/LiF(1nm)/Al(100nm)；
器件C：ITO/PEDOT:PSS(50nm)/DPEPO:化合物3(5％40nm)/TmPyPB(40nm)/LiF(1nm)/Al(100nm)。
以法国JY公司SPEX CCD3000光谱仪对上述器件A、器件B和器件C的电致发光 光谱进行测量，经计算获得如表2所示的性能数据。此外，还可以以Keithley源测量系统(Keithley 2400 Sourcemeter、Keithley 2000 Currentmeter)对上述器件A、器件B和器件C的电流-亮度-电压特性进行检测。
表2.器件A～C的性能数据
器件 最高电流效率(cd/A) CIE坐标 最大外量子效率(％)
器件1 19.8 (0.13,0.09) 16.1
器件2 21.5 (0.14,0.10) 15.7
器件3 7.3 (0.20,0.25) 3.9
由上述数据显示，器件A、器件B和器件C的电致发光色度为深蓝色。
实施例6.显示面板
在本实施例中，提供一种显示面板。如图5所示，所述显示面板200包括：一基板21，所述基板21上形成复数个所述有机电致发光器件100。所述有机电致发光器件100尤其可以是所述器件A、器件B或器件C。本领域技术人员可以理解的是，所述基板21上还可以形成有经过前序若干工序的结构，例如可能有无机膜层、薄膜晶体管结构中的若干膜层或者已经形成完整的薄膜晶体管及走线。当然，所述显示面板200还包括其他诸如封装盖板之类的已知结构，在此不在赘述。
在本发明中，通过筛选不同的电子给体单元并调节电子给体与电子受体之间的扭转角及电荷转移特性，达到减小目标分子最低单三重能级差以及高能级的目的，进而合成了一系列具有高单三线态能级、优良发光性能的化合物。该些化合物可以作为荧光材料，尤其是作为深蓝色热激活延迟荧光材料而包含于有机发光层，从而制成一系列高性能的电致热激活延迟荧光器件。
本申请已由上述相关实施例加以描述，然而上述实施例仅为实施本申请的范例。必需指出的是，已公开的实施例并未限制本申请的范围。相反地，包含于权利要求书的精神及范围的修改及均等设置均包括于本申请的范围内。
工业实用性
本申请的主体可以在工业中制造和使用，具备工业实用性。

Claims (10)

  1. 一种吖啶衍生物，具有式(I)所示结构：
    Figure PCTCN2018123251-appb-100001
    其中，D代表电子给体单元，具有式(I-2-a)、(I-2-b)、(I-2-c)、(I-3-a)、(I-3-b)、(I-3-c)、(I-4-a)、(I-4-b)或(I-4-c)所示的结构：
    Figure PCTCN2018123251-appb-100002
  2. 如权利要求1所述的吖啶衍生物如权利要求1所述的吖啶衍生物，具有化合物1～3所示的结构：
    Figure PCTCN2018123251-appb-100003
  3. 一种吖啶衍生物，具有式(I)所示结构：
    Figure PCTCN2018123251-appb-100004
    其中，D代表电子给体单元，所述电子给体单元含有吖啶结构。
  4. 如权利要求3所述的吖啶衍生物，其特征在于，所述电子给体单元具有式(I-2)、(I-3)或(I-4)所示的结构：
    Figure PCTCN2018123251-appb-100005
    其中，R 2与R 1或R 3连接形成芳环；或者，R 3与R 4连接形成芳环；
    并且，Ar为取代或非取代的芳烃基团。
  5. 如权利要求4所述的吖啶衍生物，其特征在于，当所述R 2与R 1或R 3连接形成芳环时，所述电子给体单元具有式(I-2-a)或(I-2-b)所示的结构：
    Figure PCTCN2018123251-appb-100006
    当所述R 3与R 4连接形成芳环时，所述电子给体单元具有式(I-2-c)所示的结构：
    Figure PCTCN2018123251-appb-100007
  6. 如权利要求4所述的吖啶衍生物，其特征在于，所述Ar代表苯环。
  7. 如权利要求6所述的吖啶衍生物，其特征在于，所述电子给体单元具有式(I-3-a)、(I-3-b)、(I-3-c)、(I-4-a)、(I-4-b)或(I-4-c)所示的结构：
    Figure PCTCN2018123251-appb-100008
  8. 如权利要求3所述的吖啶衍生物，具有化合物1～3所示的结构：
    Figure PCTCN2018123251-appb-100009
  9. 一种有机电致发光器件，包括第一电极、第二电极及设置于所述第一电极与所述第二电极之间的至少一有机发光层，其中，所述有机发光层包含荧光材料，所述荧光材料选自如权利要求1所述的吖啶衍生物。
  10. 如权利要求9所述的有机电致发光器件，其特征在于，所述有机发光二极管器件还包括： 设置于所述第一电极与所述有机发光层之间的一空穴注入层，设置于所述空穴注入层与所述有机发光层之间的一空穴传输层，以及，设置于所述有机发光层与所述第二电极之间的一电子传输层。
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