Organic light-emitting device

Abstract

The invention provides an organic light-emitting device which comprises an anode, a cathode, a first organic layer and a second organic layer, the first organic layer and the second organic layer are arranged between the anode and the cathode, the first organic layer comprises a first compound with a structural general formula I shown in the specification, and the second organic layer comprises a second compound with a structural general formula II shown in the specification. The second organic layer comprises a second compound with a structural general formula as shown in a formula II, and W is selected from O or S. According to the organic light-emitting device provided by the invention, the first compound and the second compound are matched for use, so that the effects of balancing carrier transport and stabilizing excitons can be achieved at the same time, the driving voltage of the organic light-emitting device can be reduced, the luminous efficiency of the excitons can be remarkably enhanced, the efficiency of the organic light-emitting device is improved, and the service life of the organic light-emitting device is prolonged. And the device performance is better.

Description

TECHNICAL FIELD

[0001] The present application is in the field of OLED technology, in particular it relates to an organic electroluminescent device. More particularly, it relates to an organic electroluminescent device comprising a first compound having the structure of Formula I in a first organic layer and a second compound having the structure of Formula II in a second organic layer, and a display assembly comprising the same. BACKGROUND

[0002] Organic electronic devices include, but are not limited to, the following kinds: organic light emitting diodes (OLEDs), organic field effect transistors (O-FETs), organic light emitting transistors (OLETs), organic photovoltaic devices (OPVs), dye-sensitized solar cells (DSSCs), organic optical detectors, organic photoreceptors, organic field-quench devices (OFQDs), light-emitting electrochemical cells (LECs), organic laser diodes and organic electroluminescent devices.

[0003] In 1987, Tang and Van Slyke at Kodak reported a two-layer organic electroluminescent device that included an arylamine hole-transport layer and a tris-8-hydroxyquinoline-aluminum layer as the electron-transport and light-emitting layers (Applied Physics Letters, 1987, 51(12): 913-915). Upon biasing the device, green light emitted from the device. This invention laid the foundation for the development of modern organic light emitting diodes (OLEDs). State-of-the-art OLEDs can include multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more light emitting layers between the cathode and anode. Since OLEDs are self-emissive solid state devices, they offer tremendous potential for display and lighting applications. In addition, the intrinsic properties of organic materials, such as their flexibility, can make them well suited for special applications, such as fabrication on flexible substrates.

[0004] OLEDs can be categorized into three different types according to their light emission mechanism. OLEDs invented by Tang and van Slyke are fluorescent OLEDs. It only uses singlet emission. The triplet states generated in the device are wasted through a nonradiative decay channel. Therefore, the internal quantum efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation hinders the commercialization of OLEDs. In 1997, Forrest and Thompson reported phosphorescent OLEDs, which use triplet emission from heavy metals containing complexes as emitters. Therefore, both singlet and triplet states can be harvested, achieving 100% IQE. Due to its high efficiency, the discovery and development of phosphorescent OLEDs have directly contributed to the commercialization of active-matrix OLEDs (AMOLEDs). Recently, Adachi achieved high efficiency through thermally activated delayed fluorescence (TADF) of organic compounds. These emitters have small singlet-triplet gaps, making it possible for excitons to return from the triplet state to the singlet state. In TADF devices, triplet excitons can generate singlet excitons through reverse intersystem crossing, resulting in high IQE.

[0005] OLEDs can also be classified into small molecule and polymer OLEDs according to the form of materials used. Small molecules refer to any organic or organometallic materials that are not polymers. The molecular weight of small molecules can be quite large as long as they have precise structures. Dendrimers with well-defined structures are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with pendant light-emitting groups. Small molecule OLEDs can become polymer OLEDs if post-polymerization occurs during the manufacturing process.

[0006] There are various OLED manufacturing methods. Small molecule OLEDs are typically manufactured by vacuum thermal evaporation. Polymer OLEDs are manufactured by solution methods, such as spin coating, inkjet printing, and nozzle printing. Small molecule OLEDs can also be manufactured by solution methods if the materials can be dissolved or dispersed in solvents.

[0007] The emission color of OLEDs can be achieved by light-emitting material structure design. OLEDs can include one or more light-emitting layers to achieve the desired spectrum. Green, yellow, and red OLEDs, phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still have problems of blue unsaturation, short device lifetime, and high operating voltage. Commercial full-color OLED displays typically use a hybrid strategy, using blue fluorescent and yellow, red, or green phosphorescent. Currently, the rapid decrease in efficiency of phosphorescent OLEDs at high brightness is still a problem. In addition, it is desirable to have more saturated emission spectrum, higher efficiency, and longer device lifetime.

[0008] An organic electroluminescence device is a device that converts electrical energy into light by applying a voltage across the device. Generally, an organic electroluminescence device includes an anode, a cathode, and an organic layer between the anode and the cathode. The organic layer of the electroluminescence device includes a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer (containing a host material and a dopant material), an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer, etc. According to the different functions of the materials, the materials constituting the organic layer can be divided into hole injection materials, hole transport materials, electron blocking materials, host materials, light-emitting materials, electron buffer materials, hole blocking materials, electron transport materials, hole blocking materials, etc. When a bias voltage is applied to the device, holes are injected from the anode to the light-emitting layer, and electrons are injected from the cathode to the light-emitting layer. Holes and electrons meet to form excitons, and excitons recombine to emit light.

[0009] The hole injection layer commonly used at present has problems of carrier imbalance and mismatch, and the carrier balance of the device has a great influence on the light-emitting efficiency of the light-emitting layer material. Imbalanced carriers will lead to mismatch of exciton concentration and number, and thus increase the voltage and capacitance of the device, thereby increasing the power consumption of the device, and thus having an important influence on the efficiency and service life of the device. SUMMARY

[0010] The present application aims to provide a series of novel organic electroluminescence devices to solve at least part of the above problems. The novel organic electroluminescence device comprises an anode, a cathode, and a first organic layer and a second organic layer disposed between the anode and the cathode, the first organic layer comprising at least a first compound having the structure of formula I, and the second organic layer comprising at least a second compound having the structure of formula II. By using the first compound and the second compound together, the present application can simultaneously achieve the effects of balancing carrier transport and stabilizing excitons, can reduce the driving voltage of the organic electroluminescence device, can significantly enhance the light-emitting efficiency of excitons, can improve the efficiency and service life of the organic electroluminescence device, and has better device performance.

[0011] According to one embodiment of the present application, an organic electroluminescence device is disclosed, comprising:

[0012] an anode,

[0013] a cathode,

[0014] and a first organic layer and a second organic layer disposed between the anode and the cathode, wherein the first organic layer comprises a first compound, wherein the general structure of the first compound is shown as formula I:

[0015]

[0016] wherein,

[0017] each of X, Y is independently selected from NR', CR"R'", O, S or Se;

[0018] each of Z 1 , Z 2 is independently selected from O, S or Se;

[0019] each of R 1 , R 2 , R', R", R'" is independently selected from any one or a combination of more than one of hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, boryl, sulfinyl, sulfonyl, phosphinyl, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms;

[0020] each of R 1 , R 2 may be the same or different, and at least one of R 1 , R 2 , R', R", R'" has an electron withdrawing group;

[0021] the electron withdrawing group is selected from the group consisting of halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, SCN, OCN, SF5, boryl, sulfinyl, sulfonyl, phosphinyl, azaheteroaromatic ring group, and any one or combination of alkyl group having 1 to 20 carbon atoms, cycloalkyl group having 3 to 20 ring carbon atoms, heteroalkyl group having 1 to 20 carbon atoms, aralkyl group having 7 to 30 carbon atoms, alkoxy group having 1 to 20 carbon atoms, aryloxy group having 6 to 30 carbon atoms, alkenyl group having 2 to 20 carbon atoms, alkynyl group having 2 to 20 carbon atoms, aryl group having 6 to 30 carbon atoms, heteroaryl group having 3 to 30 carbon atoms, alkylsilyl group having 3 to 20 carbon atoms, arylsilyl group having 6 to 20 carbon atoms, substituted with any one or more of halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, SCN, OCN, SF5, boryl, sulfinyl, sulfonyl, phosphinyl, azaheteroaromatic ring group;

[0022] R in formula I 1 R in formula I 2 R', R", R'" can be arbitrarily bonded to each other by a linking group or a single bond to form an aliphatic ring or an aromatic ring;

[0023] the second organic layer further comprises a second compound, wherein the second compound has a general structure as shown in formula II:

[0024]

[0025] wherein

[0026] the W is selected from O or S;

[0027] the X 1 and X 2 are each independently selected from O, S or NR 3 ;

[0028] the Z 3 , Z 4 , Z 5 are each independently selected from N or CR 4 ;

[0029] the ring A, ring B are each independently selected from a substituted or unsubstituted aryl ring having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl ring having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl ring having 6 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl ring having 2 to 30 carbon atoms;

[0030] the R 3 , R 4each independently is selected from any one or a combination of more of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl with 3 to 20 carbon atoms, substituted or unsubstituted heteroalkyl with 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl with 3 to 20 carbon atoms, substituted or unsubstituted aralkyl with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy with 1 to 20 carbon atoms, substituted or unsubstituted aryloxy with 6 to 30 carbon atoms, substituted or unsubstituted alkylthio with 1 to 20 carbon atoms, substituted or unsubstituted arylthio with 6 to 30 carbon atoms, substituted or unsubstituted alkenyl with 2 to 20 carbon atoms, substituted or unsubstituted alkynyl with 2 to 20 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl with 3 to 30 carbon atoms, substituted or unsubstituted alkylsilicon with 3 to 20 carbon atoms, substituted or unsubstituted arylsilicon with 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium with 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium with 6 to 20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino;

[0031] the ring A, the ring B, and R 3 , R 4 may arbitrarily bond to each other to form an aliphatic ring or an aromatic ring through a linking group or a single bond;

[0032] According to another embodiment of the present application, a display assembly comprising the organic electroluminescent device of the above-mentioned embodiments is also disclosed.

[0033] According to another embodiment of the present application, a lighting device comprising the organic electroluminescent device of the above-mentioned embodiments is also disclosed.

[0034] According to another embodiment of the present application, a compound combination comprising a first compound and a second compound is also disclosed, wherein the first compound has a general structure as shown in Formula I:

[0035]

[0036] wherein,

[0037] each of X and Y is independently selected from NR’, CR”R’”, O, S or Se;

[0038] each of Z 1 , Z 2 is independently selected from O, S or Se;

[0039] each of R1 , R 2 , R', R", R'" are each independently selected from any one or combination of hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, boryl, sulfinyl, sulfonyl, phosphinyl, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms;

[0040] said R 1 , R 2 may be the same or different, and at least one of said R 1 , R 2 , R', R", R'" has an electron withdrawing group;

[0041] said electron withdrawing group is selected from halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, boryl, sulfinyl, sulfonyl, phosphinyl, azaheteroaromatic ring, and a combination of any one or more of alkyl having 1 to 20 carbon atoms, cycloalkyl having 3 to 20 ring carbon atoms, heteroalkyl having 1 to 20 carbon atoms, aralkyl having 7 to 30 carbon atoms, alkoxy having 1 to 20 carbon atoms, aryloxy having 6 to 30 carbon atoms, alkenyl having 2 to 20 carbon atoms, alkynyl having 2 to 20 carbon atoms, aryl having 6 to 30 carbon atoms, heteroaryl having 3 to 30 carbon atoms, alkylsilyl having 3 to 20 carbon atoms, arylsilyl having 6 to 20 carbon atoms, substituted with said electron withdrawing group;

[0042] said R 1 , R 2 , R', R", R'" in formula I can arbitrarily bond to each other through a linking group or a single bond to form an aliphatic ring or an aromatic ring;

[0043] The second compound has a general structure as shown in Formula II:

[0044]

[0045] wherein

[0046] The W is selected from O or S;

[0047] The X 1 and X 2 are each independently selected from O, S or NR 3 ;

[0048] The Z 3 , Z 4 , Z 5 are each independently selected from N or CR 4 ;

[0049] The ring A, ring B are each independently selected from a substituted or unsubstituted aryl ring having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl ring having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl ring having 6 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl ring having 2 to 30 carbon atoms;

[0050] The R 3 , R 4 are each independently selected from any one or combination of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkylthio having 1 to 20 carbon atoms, substituted or unsubstituted arylthio having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino;

[0051] The ring A, ring B and R 3 , R4 may be arbitrarily linked to each other by a linking group or a single bond to form an aliphatic ring or an aromatic ring.

[0052] The advantageous effects of the present application are as follows:

[0053] The present application provides a novel organic electroluminescent device, which comprises an anode, a cathode, and a first organic layer and a second organic layer disposed between the anode and the cathode, wherein the first organic layer comprises at least a first compound having a structure of Formula I, and the second organic layer comprises at least a second compound having a structure of Formula II. The first compound having the structure of Formula I can adjust the hole injection ability of the hole injection layer and improve the carrier balance. The second compound having the structure of Formula II is used in the light-emitting layer and has the ability to stabilize the excitons formed by holes and electrons, can significantly enhance the light-emitting efficiency of the excitons, and thus can improve the efficiency and the service life of the organic electroluminescent device. The organic electroluminescent device provided by the present application can make the device performance of the organic electroluminescent device far greater than the device performance of the organic electroluminescent device using only the first compound or the second compound by using the first compound and the second compound together. The organic electroluminescent device provided by the present application can not only adjust the carrier balance and reduce the driving voltage, but also control the generation of stable excitons in the light-emitting layer, reduce the loss of excitons other than the light-emitting process, improve the light-emitting efficiency, and prolong the service life of the device. Therefore, the organic electroluminescent device provided by the present application can significantly reduce the driving voltage, improve the light-emitting efficiency, and prolong the service life of the device, and overcome the defects of the prior art. BRIEF DESCRIPTION OF DRAWINGS

[0054] Figure 1 is a schematic diagram of an organic light-emitting device according to an embodiment of the present specification;

[0055] Figure 1 The device 100 in the embodiment comprises a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190.

[0056] Figure 2 is a schematic diagram of an organic light-emitting device with an encapsulation layer according to an embodiment of the present specification;

[0057] Figure 2 The device 200 in the embodiment comprises a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, a cathode 190, and an encapsulation layer 102. DETAILED DESCRIPTION

[0058] For a more complete understanding of the present application, reference is now made to the following descriptions taken in conjunction with the accompanying drawings in which preferred embodiments of the application are shown. It is to be understood that the following description is illustrative of the application and is not to be limiting of the scope of the application. With specific reference to the drawings in detail, it is stated that the particulars shown are by way of example and for purposes of illustrative discussion of the preferred embodiments of the present application only and are not limiting of the scope of the application. Other embodiments of the present application can be devised without departing from the spirit or the scope of the present application. Examples and comparative examples provided in the specification are presented by way of example only and are not intended to limit the scope of the application. The examples and comparative examples provided in the specification are provided to more fully describe and disclose the application.

[0059] The organic compounds of the present application are suitable for use in light-emitting elements, display panels, and electronic devices, and in particular, in organic electroluminescent devices. The electronic device of the present application is a device including a layer of at least one organic compound, and the device can also include a layer of inorganic material or be formed entirely of inorganic material. The electronic device is preferably an organic electroluminescent device (OLED), an organic integrated circuit (O-IC), an organic field effect transistor (O-FET), an organic thin film transistor (O-TFT), an organic light-emitting transistor (O-LET), an organic solar cell (O-SC), an organic dye-sensitized solar cell (O-DSSC), an organic optical detector, an organic photoreceptor, an organic field-quench device (O-FQD), a light-emitting electrochemical cell (LEC), an organic laser diode (O-laser), and an organic plasmonic emitter. The electronic device is preferably an organic electroluminescent device (OLED).

[0060] OLEDs can be fabricated on a variety of substrates, such as glass, plastic, and metal. Figure 1 An organic light emitting device 100 is schematically, non-limitingly illustrated. The figures are not necessarily drawn to scale and some layer structures in the figures can be omitted as desired. The device 100 can include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190. The device 100 can be fabricated by sequentially depositing the layers described. The properties and functions of the layers, as well as exemplary materials, are described in more detail in U.S. Patent No. 7,279,704 B2, columns 6-10, the entire contents of which are incorporated by reference.

[0061] Each of these layers has more examples. For example, flexible and transparent substrate-anode combinations are disclosed in U.S. Patent No. 5,844,363, incorporated by reference in its entirety. An example of a p-doped hole-transporting layer is m-MTDATA doped with F4-TCNQ in a 50:1 molar ratio, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, incorporated by reference in its entirety. Examples of host materials are disclosed in U.S. Patent No. 6,303,238, issued to Thompson et al., incorporated by reference in its entirety. An example of an n-doped electron-transporting layer is BPhen doped with Li in a 1:1 molar ratio, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, incorporated by reference in its entirety. U.S. Patent Nos. 5,703,436 and 5,707,745, incorporated by reference in their entirety, disclose examples of cathodes, including composite cathodes with a thin layer of metal, such as Mg:Ag, overlying a transparent, conductive, sputter-deposited ITO layer. The principles and use of a blocking layer are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, incorporated by reference in their entirety. Examples of injection layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, incorporated by reference in its entirety. A description of a protective layer can be found in U.S. Patent Application Publication No. 2004 / 0174116, incorporated by reference in its entirety.

[0062] The layered structure described above is provided by way of non-limiting example. The function of an OLED can be achieved by combining various layers described above, or some layers can be omitted entirely. It can also include other layers not explicitly described. Within each layer, a single material or a mixture of materials can be used to achieve optimal performance. Any functional layer can include several sub-layers. For example, an emissive layer can have two sub-layers of different emissive materials to achieve a desired emission spectrum.

[0063] In one embodiment, an OLED can be described as having a "substrate-anode-organic layer-cathode" structure. The organic layer can include one or more layers.

[0064] OLEDs also require encapsulation layers, such as Figure 2 An illustrative, non-limiting organic light emitting device 200 is shown, which is similar to Figure 1Differently, the cathode 190 can also include an encapsulation layer 102 on top to prevent harmful species from the environment, such as moisture and oxygen. Any material capable of providing an encapsulation function can be used as the encapsulation layer, such as glass or organic-inorganic hybrid layers. The encapsulation layer should be placed directly or indirectly on the outside of the OLED device. Multilayer thin film encapsulation is described in U.S. Patent No. 7,968,146 B2, which is incorporated herein by reference in its entirety.

[0065] Devices fabricated in accordance with embodiments of the application can be incorporated into a variety of consumer products, which have one or more electronic component modules (or units) that incorporate the device. Some examples of these consumer products include a flat panel display, a monitor, a medical monitor, a television, a billboard, a lamp for indoor or outdoor illumination and / or signaling, a heads up display, a fully or partially transparent display, a flexible display, a smart phone, a tablet computer, a phablet, a wearable device, a smart watch, a laptop computer, a digital camera, a camcorder, a viewfinder, a microdisplay, a 3-D display, a vehicle display and tail lamp.

[0066] The materials and structures described herein can also be used in other organic electronic devices, which are listed above.

[0067] As used herein, "top" means farthest from the substrate, and "bottom" means closest to the substrate. Where a first layer is described as "disposed" on a second layer, the first layer is disposed farther from the substrate. Unless specified that a first layer is "in contact with" a second layer, there can be other layers between the first and second layers. For example, a cathode can be described as "disposed on" an anode, even though various organic layers are between the cathode and the anode.

[0068] As used herein, "solution processible" means capable of being dissolved, dispersed, or transported in and / or deposited from a liquid medium, either in solution or suspension form.

[0069] A ligand can be referred to as "photosensitive" when it is believed to directly contribute to the photoactive properties of the emissive material. A ligand can be referred to as "auxiliary" when it is believed not to contribute to the photoactive properties of the emissive material, but an auxiliary ligand can alter the properties of a photosensitive ligand.

[0070] It is believed that the internal quantum efficiency (IQE) of fluorescent OLEDs can be exceeded by 25% of the spin-statistics limit by delayed fluorescence. Delayed fluorescence can be generally classified into two types, P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).

[0071] On the other hand, E-type delayed fluorescence does not depend on the collision of two triplets, but rather on the conversion between a triplet and a singlet excited state. Compounds capable of E-type delayed fluorescence need to have a small singlet-triplet gap so that the conversion between the states can occur. Thermal energy can activate the transition from triplet back to singlet. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). A notable feature of TADF is that the delayed component increases with increasing temperature. If the rate of reverse intersystem crossing (RISC) is fast enough to minimize non-radiative decay from triplet, the fraction of singlet excited states that are refilled can reach 75%. The total singlet fraction can be 100%, far exceeding the 25% of spin statistics for electroluminescent excitons.

[0072] E-type delayed fluorescence characteristics can be found in exciplex systems or in single compounds. Without being bound by theory, it is believed that E-type delayed fluorescence requires that the light-emitting material have a small singlet-triplet energy gap (ΔES-T). Organic non-metal-containing donor-acceptor light-emitting materials can be able to achieve this. Emission from these materials is often characterized as donor-acceptor charge transfer (CT) type emission. The spatial separation of the HOMO and LUMO in these donor-acceptor type compounds often results in a small ΔES-T. These states can include CT states. Typically, donor-acceptor light-emitting materials are constructed by linking an electron donor moiety (such as an amino or carbazole derivative) with an electron acceptor moiety (such as a N-containing six-membered aromatic ring).

[0073] Definitions of terms for substituents

[0074] Halogen or halide - as used herein, includes fluorine, chlorine, bromine and iodine.

[0075] Alkyl - as used herein, includes straight-chain and branched-chain alkyl groups. Alkyl groups can be alkyl groups having 1 to 30 carbon atoms, preferably alkyl groups having 1 to 12 carbon atoms, more preferably alkyl groups having 1 to 6 carbon atoms. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, 3-methylpentyl. Of the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, n-pentyl, neopentyl and n-hexyl are preferred. Additionally, alkyl groups can be optionally substituted.

[0076] Cycloalkyl - As used herein, cycloalkyl includes cyclic alkyl groups. Cycloalkyl groups can be cycloalkyl groups having 3 to 30 ring carbon atoms, preferably cycloalkyl groups having 4 to 10 ring carbon atoms. Examples of cycloalkyl groups include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, and the like. Of the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl are preferred. Additionally, the cycloalkyl group can be optionally substituted.

[0077] Heteroalkyl - As used herein, heteroalkyl includes groups in which one or more carbons of an alkyl group are replaced with a heteroatom selected from the group consisting of nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium, and boron. Heteroalkyl groups can be heteroalkyl groups having 1 to 30 carbon atoms, preferably heteroalkyl groups having 1 to 10 carbon atoms, more preferably heteroalkyl groups having 1 to 6 carbon atoms. Examples of heteroalkyl groups include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxy methyl, ethoxymethoxy methyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermylmethyl, trimethylgermylethyl, trimethylgermylisopropyl, dimethylethylgermylmethyl, dimethylisopropylgermylmethyl, t-butyldimethylgermylmethyl, triethygermylmethyl, triethygermylethyl, triisopropylgermylmethyl, triisopropylgermylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl, triisopropylsilylethyl. Additionally, the heteroalkyl group can be optionally substituted.

[0078] Alkenyl - As used herein, alkenyl encompasses straight-chain, branched, and cyclic alkene groups. Alkenyl groups can be alkenyl groups containing 2 to 30 carbon atoms, preferably alkenyl groups having 2 to 10 carbon atoms. Examples of alkenyl groups include ethenyl, propenyl, 1 -butenyl, 2-butenyl, 3-butenyl, 1,3-butanedienyl, 1 -methylvinyl, phenethenyl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1 -methylallyl, 1,1 -dimethylallyl, 2-methylallyl, 1 -phenylallyl, 2-phenylallyl, 3-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1 -phenyl- 1 -butenyl, 3-phenyl- 1 -butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cycloheptatrienyl, cyclooctenyl, cyclooctatetraenyl, and norbornenyl. Additionally, the alkenyl group can be optionally substituted.

[0079] Alkynyl - As used herein, encompasses straight chain alkynyl groups. The alkynyl group can be an alkynyl group comprising 2 to 30 carbon atoms, preferably an alkynyl group having 2 to 10 carbon atoms. Examples of alkynyl groups include ethynyl, propynyl, propargyl, 1 -butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3,3-dimethyl-1 -butynyl, 3-ethyl-3-methyl-1-pentynyl, 3,3-diisopropyl 1-pentynyl, phenylethynyl, phenylpropynyl, and the like. Of the above, ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, and phenylethynyl are preferred. Additionally, the alkynyl group can be optionally substituted.

[0080] Aryl or aromatic - As used herein, both non-fused and fused systems are contemplated. The aryl group can be an aryl group having 6 to 50 carbon atoms, preferably 6 to 20 carbon atoms, more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthyl, anthryl, pyrenyl, phenanthryl, fluorenyl, pyryl, perylenyl, and azulenyl, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorenyl, and naphthyl. Examples of non-fused aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, and m-quaterphenyl. Additionally, the aryl group can be optionally substituted.

[0081] Heterocyclyl or heterocycle - As used herein, non-aromatic cyclic groups are contemplated. Non-aromatic heterocyclyl groups include saturated heterocyclic groups having 3 to 20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3 to 20 ring atoms, wherein at least one ring atom is selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a silicon atom, a phosphorus atom, a germanium atom, and a boron atom, with preferred non-aromatic heterocyclyl groups being those having 3 to 7 ring atoms, including at least one heteroatom such as nitrogen, oxygen, silicon, or sulfur. Examples of non-aromatic heterocyclyl groups include oxiranyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxolanyl, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxepinyl, thiepinyl, azepinyl, and tetrahydrothiopyranyl. Additionally, the heterocyclyl group can be optionally substituted.

[0082] Heteroaryl - As used herein, a non-fused and fused heteroaromatic group that can contain 1 to 5 heteroatoms, at least one of which is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium and boron. Heteroaryl also refers to heteroaryl. The heteroaryl group can be a heteroaryl group having 3 to 30 carbon atoms, preferably a heteroaryl group having 3 to 20 carbon atoms, more preferably a heteroaryl group having 3 to 12 carbon atoms. Suitable heteroaryls include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoseleophene, carbazole, indolocarbazole, pyridinoindole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazol, indolizine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthridine, phtalazine, pteridine, xanthene, acridine, phenoxazine, phenothiazine, benzofuro[3,2-b]pyridine, furo[3,2-b]dipyridine, benzothieno[3,2-b]pyridine, thieno[3,2-b]dipyridine, benzoseleto[3,2-b]pyridine, seleto[3,2-b]dipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazole and nitrogen analogs thereof. Additionally, the heteroaryl group can be optionally substituted.

[0083] Alkoxy - As used herein, represented by -O-alkyl, -O-cycloalkyl, -O-heteroalkyl or -O-heterocyclyl. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl and heterocyclyl are the same as described above. The alkoxy group can be an alkoxy group having 1 to 20 carbon atoms, preferably an alkoxy group having 1 to 6 carbon atoms. Examples of alkoxy groups include methoxy, ethoxy, propoxy, butoxy, pentoxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy and ethoxymethyloxy. Additionally, the alkoxy group can be optionally substituted.

[0084] Aryloxy - As used herein, represented by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl are the same as described above. The aryloxy group can be an aryloxy group having 6 to 30 carbon atoms, preferably an aryloxy group having 6 to 20 carbon atoms. Examples of aryloxy groups include phenoxy and biphenyloxy. Additionally, the aryloxy group can be optionally substituted.

[0085] Arylalkyl - as used herein, encompasses an aryl group substituted with an alkyl group. The arylalkyl group can be an arylalkyl group having from 7 to 30 carbon atoms, preferably an arylalkyl group having from 7 to 20 carbon atoms, more preferably an arylalkyl group having from 7 to 13 carbon atoms. Examples of arylalkyl groups include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl-t-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthylethyl, 2-β-naphthylethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, p-methylbenzyl, m-methylbenzyl, o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl, o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl, o-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-hydroxybenzyl, p-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-hydroxy-2-phenylisopropyl and 1-chloro-2-phenylisopropyl. Of the foregoing, benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl and 2-phenylisopropyl are preferred. Additionally, the arylalkyl group can be optionally substituted.

[0086] Alkylsilyl - as used herein, encompasses an alkyl group substituted with a silyl group. The alkylsilyl group can be an alkylsilyl group having from 3 to 20 carbon atoms, preferably an alkylsilyl group having from 3 to 10 carbon atoms. Examples of alkylsilyl groups include trimethylsilyl, triethylsilyl, methyldiethylsilyl, ethyldimethylsilyl, tripropylsilyl, tributylsilyl, triisopropylsilyl, methyldiisopropylsilyl, dimethylisopropylsilyl, tri-t-butylsilyl, triisobutylsilyl, dimethyl-t-butylsilyl, methyldi-t-butylsilyl. Additionally, the alkylsilyl group can be optionally substituted.

[0087] Arylsilyl - as used herein, encompasses a silyl group substituted with at least one aryl group. The arylsilyl group can be an arylsilyl group having from 6 to 30 carbon atoms, preferably an arylsilyl group having from 8 to 20 carbon atoms. Examples of arylsilyl groups include triphenylsilyl, phenyldiphenylsilyl, diphenylphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, diphenyl-t-butylsilyl. Additionally, the arylsilyl group can be optionally substituted.

[0088] Alkylgermyl - As used herein, encompasses an alkyl-substituted germyl group. The alkylgermyl group can be an alkylgermyl group having 3 to 20 carbon atoms, preferably an alkylgermyl group having 3 to 10 carbon atoms. Examples of alkylgermyl groups include trimethylgermyl, triethylgermyl, methyldiethylgermyl, ethyldimethylgermyl, tripropylgermyl, tributylgermyl, triisopropylgermyl, methyldiisopropylgermyl, dimethylisopropylgermyl, tri-t-butylgermyl, triisobutylgermyl, dimethyl-t-butylgermyl, methyldi-t-butylgermyl. Additionally, the alkylgermyl group can be optionally substituted.

[0089] Arylgermyl - As used herein, encompasses a germyl group substituted with at least one aryl or heteroaryl group. The arylgermyl group can be an arylgermyl group having 6 to 30 carbon atoms, preferably an arylgermyl group having 8 to 20 carbon atoms. Examples of arylgermyl groups include triphenylgermyl, phenyldiphenylgermyl, diphenylphenylgermyl, phenyldiethylgermyl, diphenylethylgermyl, phenyldimethylgermyl, diphenylmethylgermyl, phenyldiisopropylgermyl, diphenylisopropylgermyl, diphenylbutylgermyl, diphenylisobutylgermyl, diphenyl-t-butylgermyl. Additionally, the arylgermyl group can be optionally substituted.

[0090] The term "aza" in azadibenzofurans, azadibenzothiophenes, and the like, means that one or more C-H groups in the corresponding aromatic fragment are replaced with a nitrogen atom. For example, azatriphenylenes include dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline, and other analogs having two or more nitrogens in the ring system. Other nitrogen analogs of the above aza derivatives will occur to those of ordinary skill in the art and all such analogs are intended to be encompassed by the terms described herein.

[0091] In the present disclosure, when any of the terms from the group consisting of substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted silylalkyl, substituted silylaryl, substituted germylalkyl, substituted germylaryl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxylic acid, substituted ester, substituted sulfinyl, substituted sulfonyl, and substituted phosphine is used, unless otherwise defined, it means that any of the alkyl, cycloalkyl, heteroalkyl, heterocyclyl, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, silylalkyl, silylaryl, germylalkyl, germylaryl, amino, acyl, carbonyl, carboxylic acid, ester, sulfinyl, sulfonyl, and phosphine groups can be substituted with one or more of deuterium, halogen, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted cycloalkyl having 3 to 20 carbon atoms, unsubstituted heteroalkyl having 1 to 20 carbon atoms, unsubstituted heterocyclyl having 3 to 20 ring atoms, unsubstituted aralkyl having 7 to 30 carbon atoms, unsubstituted alkoxy having 1 to 20 carbon atoms, unsubstituted aryloxy having 6 to 30 carbon atoms, unsubstituted alkenyl having 2 to 20 carbon atoms, unsubstituted alkynyl having 2 to 20 carbon atoms, unsubstituted aryl having 6 to 30 carbon atoms, unsubstituted heteroaryl having 3 to 30 carbon atoms, unsubstituted silylalkyl having 3 to 20 carbon atoms, unsubstituted silylaryl having 6 to 20 carbon atoms, unsubstituted germylalkyl having 3 to 20 carbon atoms, unsubstituted germylaryl having 6 to 20 carbon atoms, unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphine, and combinations thereof.

[0092] It should be understood that when a molecular fragment is described as a substituent or otherwise attached to another moiety, its name can be written depending on whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuryl) or depending on whether it is an entire molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying substituents or attached fragments are considered to be equivalent.

[0093] In the compounds mentioned in the present disclosure, hydrogen atoms can be partially or completely replaced by deuterium. Other atoms such as carbon, nitrogen, oxygen, sulfur, phosphorus, silicon, and boron, etc. can also be replaced by their other stable isotopes. The replacement of other stable isotopes in the compounds can be preferred due to its enhanced efficiency and stability of the device.

[0094] In the compounds mentioned in the present disclosure, multiple substitution means including double substitution up to the maximum available substitution. When a substituent in the compounds mentioned in the present disclosure represents multiple substitution (including double substitution, triple substitution, quadruple substitution, etc.), it means that the substituent can exist at multiple available substitution positions on the structure to which it is connected, and the substituent that exists at multiple available substitution positions can be the same structure or different structures.

[0095] In the compounds mentioned in the present disclosure, unless explicitly defined, for example, adjacent substituents can be optionally connected to form a ring, adjacent substituents in the compounds cannot be connected to form a ring. In the compounds mentioned in the present disclosure, adjacent substituents can be optionally connected to form a ring, which includes both the case where adjacent substituents can be connected to form a ring and the case where adjacent substituents are not connected to form a ring. When adjacent substituents can be optionally connected to form a ring, the formed ring can be a single ring or a multiple ring (including a spiro ring, a bridged ring, a fused ring, etc.), and an alicyclic ring, a heteroalicyclic ring, an aromatic ring, or a heteroaromatic ring. In this expression, adjacent substituents can refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to further away carbon atoms. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.

[0096] The expression that adjacent substituents can be optionally connected to form a ring is also intended to mean that two substituents bonded to the same carbon atom are connected to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

[0097]

[0098] The expression that adjacent substituents can be optionally connected to form a ring is also intended to mean that two substituents bonded to carbon atoms directly bonded to each other are connected to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

[0099]

[0100] The expression that adjacent substituents can be optionally connected to form a ring is also intended to mean that two substituents bonded to further away carbon atoms are connected to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

[0101]

[0102] In addition, the expression that adjacent substituents can be optionally connected to form a ring is also intended to mean that, in the case where one of the two adjacent substituents represents hydrogen, the second substituent is bonded at the position to which the hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following formula:

[0103]

[0104] According to one embodiment of the present application, an organic electroluminescence device is disclosed, comprising:

[0105] an anode,

[0106] a cathode,

[0107] and a first organic layer and a second organic layer disposed between the anode and the cathode, wherein the first organic layer comprises a first compound, wherein the first compound has a general structure according to Formula I:

[0108]

[0109] wherein in Formula I,

[0110] X and Y are on each occurrence, identically or differently, selected from NR’, CR”R”’, O, S, or Se;

[0111] Z 1 and Z 2 are on each occurrence, identically or differently, selected from O, S, or Se;

[0112] R 1 , R 2 , R’, R” and R”’ are on each occurrence, identically or differently, selected from the group consisting of hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, SCN, OCN, SF5, boryl, sulfinyl, sulfonyl, phosphinyl, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, and combinations thereof;

[0113] R 1 , R 2 may be the same or different, and R 1 , R 2 , R’, R” and R”’ at least one is a group having at least one electron withdrawing group;

[0114] R1 R 2 R', R", R'" can be arbitrarily bonded to each other by a linking group or a single bond to form a ring;

[0115] The second organic layer further comprises a second compound, wherein the general structure of the second compound is shown as Formula II:

[0116]

[0117] wherein in Formula II,

[0118] W is selected from O or S, the same or different at each occurrence;

[0119] X 1 and X 2 is selected from O, S or NR 3 , the same or different at each occurrence;

[0120] Z 3 , Z 4 , Z 5 is selected from N or CR 4 , the same or different at each occurrence;

[0121] Ring A, Ring B are each independently selected from a substituted or unsubstituted aryl ring having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl ring having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl ring having 6 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl ring having 2 to 30 carbon atoms, and combinations thereof;

[0122] R 3 , R 4each occurrence is the same or different selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl with 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl with 3 to 20 ring atoms, substituted or unsubstituted aralkyl with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy with 1 to 20 carbon atoms, substituted or unsubstituted aryloxy with 6 to 30 carbon atoms, substituted or unsubstituted alkylthio with 1 to 20 carbon atoms, substituted or unsubstituted arylthio with 6 to 30 carbon atoms, substituted or unsubstituted alkenyl with 2 to 20 carbon atoms, substituted or unsubstituted alkynyl with 2 to 20 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl with 3 to 30 carbon atoms, substituted or unsubstituted alkylsilicon with 3 to 20 carbon atoms, substituted or unsubstituted arylsilane with 6 to 20 carbon atoms, substituted or unsubstituted alkyl germanium with 3 to 20 carbon atoms, substituted or unsubstituted aryl germanium with 6 to 20 carbon atoms, substituted or unsubstituted amino with 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0123] ring A, ring B, and R 3 in formula II can optionally be bonded to each other to form a ring through a linking group or a single bond. 4 in formula II can optionally be bonded to each other to form a ring through a linking group or a single bond.

[0124] In the present embodiment, adjacent substituents in formula I, formula II can optionally be bonded to each other to form a ring through a linking group or a single bond, is intended to mean that, in formula I, formula II, any one or more of the following groups of adjacent substituents, for example, adjacent substituents R 1 or R 2 and R”, adjacent substituents R 1 or R 2 and R’, adjacent substituents R 1 or R 2 and R’”, and two adjacent substituents R 1 and R 2 may be connected to form a ring. Obviously, none of these groups of adjacent substituents can also be connected to form a ring.

[0125] In the present embodiment, the aryl ring or aryl group can be a monocyclic or polycyclic ring, as examples of a monocyclic aryl group, there are phenyl, biphenyl, terphenyl, stilbenyl, and the like, as examples of a polycyclic aryl group, there are naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, tetracenyl, fluorenyl, acenaphthenyl trisphenyl, fluoranthenyl, and the like, but the scope of the present application is not limited to only these examples.

[0126] In the present embodiment, the heteroaryl ring or heteroaryl group is an aromatic ring containing 1 or more heteroatoms, as examples thereof, there are thienyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolyl, quinoxalyl, phthalazinyl, pyridopyrimidyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, dibenzofuranyl, phenanthrolinyl, thiazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, and the like, but not limited to only these.

[0127] In the present embodiment, the cycloalkyl ring refers to a ring that is not aromatic and is composed of only carbon and hydrogen atoms, examples thereof include a monocyclic or polycyclic ring, and can be further substituted with other substituents, the polycyclic ring refers to a group that is directly connected or fused to other ring groups, and the other ring groups can also refer to aliphatic hydrocarbon rings, but can also be other types of ring groups, such as aliphatic heterocyclic rings, aryl groups, heteroaryl groups, and the like. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, adamantyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like cycloalkyl groups; and cyclohexane, cyclopentane, and the like cycloalkanes; and cyclohexene, cyclobutene, and the like cycloalkenes, and are not limited to only these.

[0128] In the present embodiment, the heterocycloalkyl ring refers to an aliphatic ring containing 1 or more heteroatoms, which contains O, S, Se, N, P, or Si, and the like heteroatoms, and also includes a monocyclic or polycyclic ring, and can be further substituted with other substituents, the polycyclic ring refers to a group that is directly connected or fused to other ring groups, and the other ring groups can also refer to aliphatic heterocyclic rings, but can also be other types of ring groups, such as aliphatic hydrocarbon rings, aryl groups, heteroaryl groups, and the like.

[0129] In the present embodiment, the aliphatic-aromatic mixed ring or aliphatic-aromatic mixed ring group refers to a ring in which two or more rings are fused to each other and the entire molecule has non-aromacity, and in addition, the polycyclic non-aromatic fused heterocycle refers to a non-aromatic fused hydrocarbon ring that contains a heteroatom selected from N, O, P, and S in addition to C, and as examples thereof, tetralin, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene, 1,2,3,4,4a,9b-hexahydrodibenzofuran, 2,3,4,4a,9,9a-hexahydro-4a,9a-dimethyl-1H-carbazole, 5,6,7,8-tetrahydroquinoline, and the like can be given, and are not limited thereto.

[0130] According to one embodiment of the present application, wherein in formula I, X and Y are the same or different at each occurrence selected from CR"R"' or NR', R', R" and R'" are groups having at least one electron withdrawing group; preferably, R, R', R" and R'" are groups having at least one electron withdrawing group.

[0131] According to one embodiment of the present application, wherein in formula I, R 1 , R 2 are the same or different at each occurrence selected from CR"R"' or NR', R', R" and R'" are groups having at least one electron withdrawing group; preferably, R 1 , R 2 are groups having at least one electron withdrawing group.

[0132] According to one embodiment of the present application, wherein the Hammett constant of the electron withdrawing group is ≥ 0.05, preferably ≥ 0.3, more preferably ≥ 0.5.

[0133] The Hammett substituent constant value of the electron withdrawing group according to the present application is ≥ 0.05, the electron withdrawing ability is strong, and the LUMO energy level of the compound can be significantly reduced to achieve the effect of improving the charge mobility.

[0134] It should be noted that the Hammett substituent constant value includes the para constant and / or the meta constant of the Hammett substituent, as long as one of the para constant and the meta constant is greater than or equal to 0.05, it can be used as the preferred selection group of the present application.

[0135] According to one embodiment of the present application, wherein the electron withdrawing group is selected from the group consisting of: halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, SCN, OCN, SF5, boryl, sulfinyl, sulfonyl, phosphinyl, azaheteroaromatic ring group, and any of the following groups substituted with one or more of halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, SCN, OCN, SF5, boryl, sulfinyl, sulfonyl, phosphinyl, azaheteroaromatic ring group: alkyl having 1 to 20 carbon atoms, cycloalkyl having 3 to 20 ring carbon atoms, heteroalkyl having 1 to 20 carbon atoms, aralkyl having 7 to 30 carbon atoms, alkoxy having 1 to 20 carbon atoms, aryloxy having 6 to 30 carbon atoms, alkenyl having 2 to 20 carbon atoms, alkynyl having 2 to 20 carbon atoms, aryl having 6 to 30 carbon atoms, heteroaryl having 3 to 30 carbon atoms, alkylsilyl having 3 to 20 carbon atoms, arylsilyl having 6 to 20 carbon atoms, and combinations thereof;

[0136] Preferably, the electron withdrawing group is selected from the group consisting of: F, CF3, OCF3, SF5, SO2CF3, cyano, isocyano, SCN, OCN, pyrimidinyl, triazinyl, and combinations thereof.

[0137] According to one embodiment of the present application, wherein X and Y are the same or different at each occurrence selected from the group consisting of:

[0138] O, S, Se,

[0139] Preferably, X, Y are selected at each occurrence from A1;

[0140] " " indicates the position of attachment of said X, Y to the formula I.

[0141] According to one embodiment of the present application, wherein R 1 , R 2at each occurrence is the same or different selected from the group consisting of hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, SCN, OCN, SF5, boryl, sulfinyl, sulfonyl, phosphinyl, unsubstituted alkyl having 1 to 30 carbon atoms, unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, unsubstituted alkoxy having 1 to 20 carbon atoms, unsubstituted alkenyl having 2 to 20 carbon atoms, unsubstituted aryl having 6 to 30 carbon atoms, unsubstituted heteroaryl having 3 to 30 carbon atoms, and the following groups substituted with one or more of halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, SCN, OCN, SF5, boryl, sulfinyl, sulfonyl, and phosphinyl: alkyl having 1 to 20 carbon atoms, cycloalkyl having 3 to 20 ring carbon atoms, alkoxy having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, aryl having 6 to 30 carbon atoms, heteroaryl having 3 to 30 carbon atoms, and combinations thereof;

[0142] According to one embodiment of the present application, R 1 , R 2 at each occurrence is the same or different selected from the group consisting of hydrogen, deuterium, methyl, isopropyl, NO2, SO2CH3, SCF3, C2F5, OC2F5, OCH3, diphenylmethylsilyl, phenyl, methoxyphenyl, p-methylphenyl, 2,6-diisopropylphenyl, biphenyl, polyfluorophenyl, difluoropyridyl, nitrophenyl, dimethylthiazolyl, ethenyl substituted with one or more of CN or CF3, ethynyl substituted with one of CN or CF3, dimethylphosphinyl, diphenylphosphinyl, F, CF3, OCF3, SF5, SO2CF3, cyano, isocyano, SCN, OCN, trifluoromethylphenyl, trifluoromethoxyphenyl, bis(trifluoromethyl)phenyl, bis(trifluoromethoxy)phenyl, 4-cyanotetrafluorophenyl, phenyl or biphenyl substituted with one or more of F, CN or CF3, tetrafluoropyridyl, pyrimidinyl, triazinyl, diphenylboryl, oxaboraanthracenyl, and combinations thereof.

[0143] According to one embodiment of the present application, R 1 , R 2 at each occurrence is the same or different selected from the group consisting of the following structures:

[0144]

[0145]

[0146] represents the R 1 , R 2the position of attachment to Formula I.

[0147] According to one embodiment of the present application, wherein in a first compound represented by Formula I, R 1 , R 2 are the same.

[0148] According to one embodiment of the present application, wherein the first compound is selected from the group consisting of Compound 1 to Compound 363; the specific structures of Compound 1 to Compound 363 are described in Claim 8.

[0149] According to one embodiment of the present application, wherein the second compound has a structure represented by Formula II; wherein W is the same or different at each occurrence selected from O or S, preferably, W is selected from S; 1 and X 2 are the same or different at each occurrence selected from O, S or NR 3 , and at least one of X 1 and X 2 is selected from NR 3 ;

[0150] According to one embodiment of the present application, wherein the second compound has a structure represented by Formula II; wherein W is the same or different at each occurrence selected from O or S, preferably, W is selected from S;

[0151] According to one embodiment of the present application, wherein the second compound has a structure represented by Formula II-1 to Formula II-8:

[0152]

[0153] wherein,

[0154] Z 3 , Z 4 , Z 5 are the same or different at each occurrence selected from N or CR 4 ;

[0155] Ring A, Ring B are each independently selected from substituted or unsubstituted aryl ring having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl ring having 2 to 30 carbon atoms, substituted or unsubstituted cycloalkyl ring having 6 to 30 carbon atoms, substituted or unsubstituted heteroalkyl ring having 2 to 30 carbon atoms;

[0156] R 3 , R 4each occurrence is the same or different selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkylthio having 1 to 20 carbon atoms, substituted or unsubstituted arylthio having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilicon having 3 to 20 carbon atoms, substituted or unsubstituted arylsilane having 6 to 20 carbon atoms, substituted or unsubstituted alkyl germanium having 3 to 20 carbon atoms, substituted or unsubstituted aryl germanium having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxyl, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0157] ring A, ring B, and R 3 , R 4 may be arbitrarily bonded to each other to form an alicyclic ring or an aromatic ring through a linking group or a single bond.

[0158] According to one embodiment of the present application, wherein the second compound has a structure represented by Formula II-1, Formula II-2, Formula II-3, Formula II-4, or Formula II-6.

[0159] According to one embodiment of the present application, wherein ring A, ring B are each independently selected from a substituted or unsubstituted aryl ring having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl ring having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl ring having 6 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl ring having 2 to 30 carbon atoms;

[0160] Preferably, ring A, ring B are each independently selected from a substituted or unsubstituted aryl ring having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl ring having 2 to 30 carbon atoms; more preferably, ring A, ring B are each independently selected from a substituted or unsubstituted aryl ring having 6 to 30 carbon atoms.

[0161] According to one embodiment of the present application, wherein Z 3 , Z 4 , Z5 N or CR 4 , and Z 3 , Z 4 , Z 5 at least one of R 4 .

[0162] According to one embodiment of the present application, wherein Z 3 , Z 4 , Z 5 is selected from CR 4 .

[0163] According to one embodiment of the present application, wherein R 3 , R 4 is selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkylthio having 1 to 20 carbon atoms, substituted or unsubstituted arylthio having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms.

[0164] According to one embodiment of the present application, wherein at least one of ring A, ring B, aryl and heteroaryl in the structure of the second compound contains at least one of the group consisting of substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms.

[0165] According to one embodiment of the present application, wherein the specific structures of the compounds 1 to 363 are as set forth in claim 8. The second compound is selected from the group consisting of the structures of claim 14.

[0166] According to one embodiment of the present application, wherein the first organic layer further comprises a third compound; the third compound comprises any one or more compounds selected from the group consisting of triarylamine, carbazole, fluorene, spirobifluorene, thiophene, furan, phenyl, oligo-phenylenevinylene, oligofluorene, and combinations thereof.

[0167] According to one embodiment of the present application, wherein the first organic layer is a hole injection layer, and the hole injection layer is in contact with the anode.

[0168] According to one embodiment of the present application, wherein in the first organic layer, the weight ratio of the first compound and the second compound is between 10000:1 to 1:10000; preferably, the weight ratio of the first compound and the second compound is between 100:1 to 1:10000; more preferably, the weight ratio of the first compound and the second compound is between 10:1 to 1:10000.

[0169] According to one embodiment of the present application, wherein in the first organic layer, the first compound is between 0.01% to 10% of the total weight of the first organic layer; or the first compound is between 0.01% to 5% of the total weight of the first organic layer; or the first compound is between 0.01% to 3% of the total weight of the first organic layer; or the first compound is between 0.01% to 2% of the total weight of the first organic layer; or the first compound is between 0.01% to 1.5% of the total weight of the first organic layer; or the first compound is between 0.01% to 1% of the total weight of the first organic layer.

[0170] According to one embodiment of the present application, wherein the second organic layer is a light-emitting layer; the light-emitting layer comprises a host, and the second compound as a dopant.

[0171] According to one embodiment of the present application, wherein the light-emitting layer is a blue light-emitting layer.

[0172] According to one embodiment of the present application, wherein the host is an anthracene-based compound, a fluorene-based compound, or a dibenzo phosphole-based compound.

[0173] According to one embodiment of the present application, wherein the host is a partially deuterium-substituted or fully deuterium-substituted anthracene-based compound.

[0174] According to another embodiment of the present application, a display assembly is also disclosed, comprising an organic electroluminescent device, the specific structure of the organic electroluminescent device is shown in any one of the foregoing embodiments.

[0175] According to another embodiment of the present application, a lighting device comprising an organic electroluminescent device is also disclosed, which comprises a structure as described in any of the aforementioned embodiments.

[0176] According to another embodiment of the present application, a compound combination comprising a first compound and a second compound is also disclosed, wherein the first compound has a general structure as shown in Formula I:

[0177]

[0178] wherein in Formula I,

[0179] X and Y are the same or different at each occurrence and are selected from NR', CR"R"', O, S, or Se;

[0180] Z 1 and Z 2 are the same or different at each occurrence and are selected from O, S, or Se;

[0181] R 1 , R 2 , R', R", and R'" are the same or different at each occurrence and are selected from the group consisting of hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, boryl, sulfinyl, sulfonyl, phosphinyl, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, and combinations thereof;

[0182] R 1 , R 2 may be the same or different, and R 1 , R 2 , R', R", and R'" at least one of which is a group having at least one electron withdrawing group;

[0183] R 1 , R 2 , R', R", and R'" in Formula I can arbitrarily bond to each other to form a ring through a linking group or a single bond;

[0184] The general structure of the second compound is shown in Formula II:

[0185]

[0186] wherein in Formula II,

[0187] W is, on each occurrence, the same or different, selected from O or S;

[0188] X 1 and X 2 is, on each occurrence, the same or different, selected from O, S, or NR 3 ;

[0189] Z 3 , Z 4 , Z 5 is, on each occurrence, the same or different, selected from N or CR 4 ;

[0190] Ring A, Ring B are each independently selected from a substituted or unsubstituted aryl ring having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl ring having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl ring having 6 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl ring having 2 to 30 carbon atoms;

[0191] R 3 , R 4 is, on each occurrence, the same or different, selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthio having 1 to 20 carbon atoms, a substituted or unsubstituted arylthio having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, a substituted or unsubstituted aryl having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilicon having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilicon having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium having 6 to 20 carbon atoms, a substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0192] Ring A, Ring B and R 3 , R 4 may be arbitrarily bonded to each other into a ring through a linking group or a single bond.

[0193] The first compound and the second compound used in the present application can be obtained by referring to the preparation method in the prior art, which will not be described here. The preparation method of the electroluminescent device is not limited, and the preparation method of the following examples is only an example and should not be understood as a limitation. Those skilled in the art can reasonably improve the preparation method of the following examples according to the prior art. For example, the ratio of various materials in each organic layer is not particularly limited, and those skilled in the art can reasonably select within a certain range according to the prior art. In the examples of the device, the characteristics of the device are also tested using the equipment commonly used in the art in a method well known to those skilled in the art. Since those skilled in the art are aware of the above-mentioned equipment use, testing method and other related content, the inherent data of the sample can be determined and obtained without being affected, therefore the above-mentioned related content will not be described here.

[0194] Device Example 1

[0195] The present example provides an organic electroluminescent device, and the preparation method is as follows: the ITO substrate is patterned to have a light-emitting area with a size of 2 mm x 2 mm, then isopropanol, UV and ozone are used for washing, then the ITO substrate is installed on the substrate support of a vacuum deposition device and the pressure is adjusted to make the vacuum rate become 1 x 10 -7 torr. First, a hole injection layer is formed by vacuum depositing compound 70 (first compound) and HT-1 (mass ratio of compound 70 to HT-1 is 3:97) with a thickness of 10 nm on the ITO layer (anode) formed on the substrate; second, a hole transport layer is formed by vacuum depositing HT-1 with a thickness of 35 nm on the above-mentioned hole injection layer, a light-emitting layer is formed by vacuum depositing a mixture of compound BD-1 (second compound) and BH with a thickness of 30 nm on the above-mentioned hole transport layer (mass ratio of BD-1 to BH is 2:98), then a hole blocking layer is formed by vacuum depositing HB-1 with a thickness of 5 nm on the above-mentioned light-emitting layer; then an electron transport layer is formed by vacuum depositing compound ET-1 and Liq (mass ratio of ET-1 to Liq is 5:5) with a thickness of 30 nm on the above-mentioned hole blocking layer; then an electron injection layer is formed by depositing LiF with a thickness of 1 nm on the above-mentioned electron transport layer, and finally a cathode is formed by depositing aluminum (Al) with a thickness of 150 nm on the above-mentioned electron injection layer, thereby preparing an organic electroluminescent device.

[0196] Device Example 2

[0197] The method is the same as that in Device Example 1, except that compound 70 in the hole injection layer is replaced by compound 72, and the mass ratio of compound 72 to HT-1 in the hole injection layer is 3:97.

[0198] Device Example 3

[0199] The method is the same as that in Device Example 1, except that compound 70 in the hole injection layer is replaced by compound 74, and the mass ratio of compound 74 to HT-1 in the hole injection layer is 3:97.

[0200] Device Example 4

[0201] The method is the same as that in Device Example 1, except that compound BD-1 in the light-emitting layer is replaced by compound BD-2, and the mass ratio of compound BD-1 to BH in the light-emitting layer is 2:98.

[0202] Device Example 5

[0203] The method is the same as that in Device Example 1, except that compound BD-1 in the light-emitting layer is replaced by compound BD-3, and the mass ratio of compound BD-3 to BH in the light-emitting layer is 2:98.

[0204] Device Example 6

[0205] The method is the same as that in Device Example 1, except that compound 70 in the hole injection layer is replaced by compound 72, and the mass ratio of compound 72 to HT-1 in the hole injection layer is 3:97; and compound BD-1 in the light-emitting layer is replaced by compound BD-2, and the mass ratio of compound BD-2 to BH in the light-emitting layer is 2:98.

[0206] Device Example 7

[0207] The method is the same as that in Device Example 1, except that compound 70 in the hole injection layer is replaced by compound 72, and the mass ratio of compound 72 to HT-1 in the hole injection layer is 3:97; and compound BD-1 in the light-emitting layer is replaced by compound BD-3, and the mass ratio of compound BD-3 to BH in the light-emitting layer is 2:98.

[0208] Device Example 8

[0209] The method is the same as that in Device Example 1, except that compound 70 in the hole injection layer is replaced by compound 74, and the mass ratio of compound 74 to HT-1 in the hole injection layer is 3:97; and compound BD-1 in the light-emitting layer is replaced by compound BD-2, and the mass ratio of compound BD-2 to BH in the light-emitting layer is 2:98.

[0210] Device Comparative Example 1

[0211] The method is the same as that of device example 1, except that compound 70 in the hole injection layer is replaced by compound PD-1, and the mass ratio of compound PD-1 to HT-1 in the hole injection layer is 3:97.

[0212] Device comparative example 2

[0213] The method is the same as that of device example 1, except that compound 70 in the hole injection layer is replaced by compound PD-1, and the mass ratio of compound PD-1 to HT-1 in the hole injection layer is 3:97; compound BD-1 in the light-emitting layer is replaced by compound BD-2, and the mass ratio of compound BD-2 to BH in the light-emitting layer is 2:98.

[0214] Device comparative example 3

[0215] The method is the same as that of device example 1, except that compound BD-1 in the light-emitting layer is replaced by compound BD-A, and the mass ratio of compound BD-A to BH in the light-emitting layer is 2:98.

[0216] Device comparative example 4

[0217] The method is the same as that of device example 1, except that compound 70 in the hole injection layer is replaced by compound 72, and the mass ratio of compound 72 to HT-1 in the hole injection layer is 3:97; compound BD-1 in the light-emitting layer is replaced by compound BD-A, and the mass ratio of compound BD-A to BH in the light-emitting layer is 2:98.

[0218] Device comparative example 5

[0219] The method is the same as that of device example 1, except that compound 70 in the hole injection layer is replaced by compound PD-1, and the mass ratio of compound PD-1 to HT-1 in the hole injection layer is 3:97; compound BD-1 in the light-emitting layer is replaced by compound BD-A, and the mass ratio of compound BD-A to BH in the light-emitting layer is 2:98.

[0220] Part of the device structure of device examples and comparative examples in Table 1

[0221]

[0222]

[0223] The molecular structure of each layer of material is as follows:

[0224]

[0225]

[0226] The electrode preparation method and the deposition method of each functional layer in the present embodiment are conventional methods in the art, such as vacuum thermal evaporation or inkjet printing, and will not be described here.

[0227] Device performance effect

[0228] The organic electroluminescent devices provided by device examples 1-8 and device comparative examples 1-4 were tested by standard method. For this, the driving voltage, current efficiency (measured in cd / A), external quantum efficiency (EQE, measured in percentage) and device lifetime (LT95, measured in h) of the organic electroluminescent devices were determined at a current density of J = 10 mA / cm 2

[0229] The test instruments and methods for testing the performance of the above OLED devices are as follows:

[0230] Luminance was tested using a spectral scanner PhotoResearch PR-635;

[0231] Current density and turn-on voltage: tested using a digital source meter Keithley 2400;

[0232] The performance test results of the above devices are listed in Table 2.

[0233] Table 2 Device performance test results

[0234]

[0235] From the device performance test results in Table 2, it can be seen that compared with the organic electroluminescent device provided by device comparative example 5, the external quantum efficiency (EQE) of device comparative examples 1 and 2 decreased by 6% and 13% respectively, and the lifetime increased by 46% and 77% respectively. It shows that the lifetime of the organic electroluminescent device prepared by using the hole injection layer material PD-1 provided by device comparative example 5 in combination with the second compound provided by the present application has been slightly improved;

[0236] Compared with the organic electroluminescent device provided by device comparative example 5, the driving voltage of device comparative examples 3 and 4 decreased by 64% and 59% respectively, and the lifetime increased by 8.7 times and 7.7 times respectively. It shows that the driving voltage and the lifetime of the organic electroluminescent device prepared by using the first compound provided by the present application in combination with the doping material BD-A provided by device comparative example 5 have been slightly improved.

[0237] Compared with the organic electroluminescent device provided by device comparative example 5, the device examples provided by the present application have been greatly improved in voltage, external quantum efficiency and lifetime, with a voltage reduction of about 71%, an external quantum efficiency increase of 3% to 9%, and a lifetime increase of about 13 times.

[0238] ​It can be seen that the device performance of the organic electroluminescent device prepared by simultaneously using the first compound and the second compound is much better than that of the organic electroluminescent device using the first compound or the second compound alone.

[0239] The first compound provided by the present application not only has strong electron-withdrawing property, enhances the hole injection capability of the hole injection layer (the first organic layer), but also adjusts the carrier balance, thereby reducing the driving voltage of the organic electroluminescent device. The second compound provided by the present application has excellent exciton stability, can significantly enhance the light-emitting efficiency of excitons, and improve the efficiency and service life of the device. The organic electroluminescent device provided by the present application uses the first compound and the second compound, so that the device performance of the organic electroluminescent device is much better than that of the organic electroluminescent device using the first compound or the second compound alone. The organic electroluminescent device provided by the present application can not only adjust the carrier balance and reduce the driving voltage, but also control the generation of stable excitons in the light-emitting layer, reduce the loss of excitons other than the light-emitting process, improve the light-emitting efficiency, and prolong the service life of the device. Therefore, the organic electroluminescent device provided by the present application can significantly reduce the driving voltage, improve the light-emitting efficiency, and prolong the service life of the device, thereby overcoming the defects of the prior art.

[0240] The above merely describes the preferred embodiments of the present application, but the protection scope of the present application is not limited thereto. Any changes or replacements within the technical scope disclosed by the present application can be easily conceived by those skilled in the art, and should be encompassed within the protection scope of the present application. Therefore, the protection scope of the present application should be subject to the protection scope of the claims.

Claims

1. An organic electroluminescent device comprising: an anode, a cathode, and a first organic layer and a second organic layer disposed between the anode and the cathode, wherein the first organic layer comprises a first compound, wherein the first compound has a general structure according to Formula I: wherein, each of X, Y is independently selected from NR’, CR”R”’, O, S, or Se; said Z 1 , Z 2 each independently is selected from O, S or Se; said R 1 , R 2 , R', R", R'" are each independently selected from any one or a combination of more than one of hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, boryl, sulfinyl, sulfonyl, phosphinyl, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms; R 1 , R 2 may be the same or different, and at least one of R 1 , R 2 , R', R", R'" has an electron withdrawing group; the electron-withdrawing group is selected from halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, SCN, OCN, SF5, borane group, sulfinyl, sulfonyl, phosphine oxide group, and azaheteroaromatic ring group, and a combination of any one or more of alkyl group having 1 to 20 carbon atoms, cycloalkyl group having 3 to 20 ring carbon atoms, heteroalkyl group having 1 to 20 carbon atoms, aralkyl group having 7 to 30 carbon atoms, alkoxy group having 1 to 20 carbon atoms, aryloxy group having 6 to 30 carbon atoms, alkenyl group having 2 to 20 carbon atoms, alkynyl group having 2 to 20 carbon atoms, aryl group having 6 to 30 carbon atoms, heteroaryl group having 3 to 30 carbon atoms, alkylsilyl group having 3 to 20 carbon atoms, arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted; R in the formula I 1 , R 2 , R', R", R'" can be arbitrarily bonded to each other into a ring through a linking group or a single bond; the second organic layer further comprises a second compound, wherein the second compound has a general structure according to Formula II: wherein W is selected from O or S; said X 1 and X 2 each independently is selected from O, S or NR 3 ; The Z 3 , Z 4 , Z 5 are each independently selected from N or CR 4 ; each of ring A, ring B is independently selected from substituted or unsubstituted aryl ring having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl ring having 2 to 30 carbon atoms, substituted or unsubstituted cycloalkyl ring having 6 to 30 carbon atoms, substituted or unsubstituted heteroalkyl ring having 2 to 30 carbon atoms; said R 3 , R 4 each independently is selected from any one or a combination of more than one of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group with 3 to 20 carbon atoms, substituted or unsubstituted heteroalkyl group with 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl group with 3 to 20 carbon atoms, substituted or unsubstituted aralkyl group with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy group with 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group with 6 to 30 carbon atoms, substituted or unsubstituted alkylthio group with 1 to 20 carbon atoms, substituted or unsubstituted arylthio group with 6 to 30 carbon atoms, substituted or unsubstituted alkenyl group with 2 to 20 carbon atoms, substituted or unsubstituted alkynyl group with 2 to 20 carbon atoms, substituted or unsubstituted aryl group with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group with 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group with 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group with 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl group with 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl group with 6 to 20 carbon atoms, substituted or unsubstituted amino group, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphino group; The ring A, the ring B and R 3 in the formula II 4 may be arbitrarily bonded to each other into a ring through a linking group or a single bond.

2. The organic electroluminescent device of claim 1, wherein each of X, Y is independently selected from CR”R”’ or NR’, and R’, R”, R”’ has at least one electron-withdrawing group.

3. The organic electroluminescent device of claim 2, wherein each of X, Y is independently selected from the group consisting of: O, S, Se, * indicates the position of attachment of X, Y to Formula I.

4. The organic electroluminescent device according to claim 1, wherein at least one of R 1 , R 2 has an electron-withdrawing group. said R 1 , R 2 each independently is selected from the group consisting of hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, boryl, sulfinyl, sulfonyl, phosphinyl, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms; When any of the R 1 , R 2 , R 1 , R 2 has a substituent, the substituent can be one or more, and each is independently selected from any one or a combination of two or more of halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, and phosphineoxy.

5. The organic electroluminescent device of claim 4, said R 1 , R 2 are each independently selected from any one or a combination of several of hydrogen, deuterium, methyl, isopropyl, NO2, SO2CH3, SCF3, C2F5, OC2F5, OCH3, diphenylmethylsilyl, phenyl, methoxyphenyl, p-methylphenyl, 2,6-diisopropylphenyl, biphenyl, polyfluorophenyl, difluoropyridyl, nitrophenyl, dimethylthiazolyl, ethenyl substituted with one or more of CN or CF3, ethynyl substituted with one of CN or CF3, dimethylphosphinyl, diphenylphosphinyl, F, CF3, OCF3, SF5, SO2CF3, cyano, isocyano, SCN, OCN, trifluoromethylphenyl, trifluoromethoxyphenyl, bis(trifluoromethyl)phenyl, bis(trifluoromethoxy)phenyl, 4-cyanotetrafluorophenyl, phenyl or biphenyl substituted with one or more of F, CN or CF3, tetrafluoropyridyl, pyrimidinyl, triazinyl, diphenylborinyl, oxaboraanthracenyl.

6. The organic electroluminescent device according to claim 5, wherein the R 1 , R 2 are each independently selected from the group consisting of the following structures: represents the R 1 , R 2 group and the position of attachment to the formula I.

7. The organic electroluminescent device of claim 1, wherein the electron-withdrawing group is selected from F, CF3, OCF3, SF5, SO2CF3, cyano, isocyano, SCN, OCN, pyrimidinyl, triazinyl, any one or a combination of any one or more of.

8. The organic electroluminescent device according to claim 1, wherein The compound of formula I is selected from the group consisting of compound 1 to compound 363; wherein, Z 1 , Z 2 are the same, X, Y are the same, Z 1 , Z 2 , X, Y, R 1 , R 2 correspond to an atom or a group selected from the following table, respectively: The hydrogens in the compounds 1 to 363 can each independently be substituted with deuterium.

9. The organic electroluminescent device of claim 1, wherein the compound according to Formula II is selected from one of the compounds according to Formula II-1 to II-8: wherein, Z 3 , Z 4 , Z 5 are each independently selected from N or CR 4 ; each of the rings A, B is independently selected from a substituted or unsubstituted aryl ring having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl ring having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl ring having 6 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl ring having 2 to 30 carbon atoms; said R 3 , R 4 each independently is selected from any one or a combination of more than one of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl with 3 to 20 carbon atoms, substituted or unsubstituted heteroalkyl with 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl with 3 to 20 ring atoms, substituted or unsubstituted aralkyl with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy with 1 to 20 carbon atoms, substituted or unsubstituted aryloxy with 6 to 30 carbon atoms, substituted or unsubstituted alkylthio with 1 to 20 carbon atoms, substituted or unsubstituted arylthio with 6 to 30 carbon atoms, substituted or unsubstituted alkenyl with 2 to 20 carbon atoms, substituted or unsubstituted alkynyl with 2 to 20 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl with 3 to 30 carbon atoms, substituted or unsubstituted alkylsilicon with 3 to 20 carbon atoms, substituted or unsubstituted arylsilicon with 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium with 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium with 6 to 20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino; Rings A, B and R 3 , R 4 may be arbitrarily bonded to each other by a linking group or a single bond to form an aliphatic ring or an aromatic ring.

10. The organic electroluminescent device according to claim 9, wherein the Z 3 , Z 4 , Z 5 are each independently selected from N or CR 4 , and Z 3 , Z 4 , Z 5 at least one of which is selected from CR 4 .

11. The organic electroluminescent device according to claim 9, wherein, when any of the rings A, B has a substituent, the substituent of the rings A, B can be one or more, and is each independently selected from any one or a combination of more of an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a heteroalkyl group having 1 to 20 carbon atoms, a heterocyclic group having 3 to 20 carbon atoms, and an aralkyl group having 7 to 30 carbon atoms.

12. The organic electroluminescent device according to claim 9, wherein the compound represented by Formula II is selected from the group consisting of: The hydrogens in the above represented structures can each independently be replaced with deuterium.

13. The organic electroluminescent device according to claim 1, wherein the first organic layer further comprises a third compound; and the third compound comprises any one or a combination of more of a triarylamine, a carbazole, a fluorene, a spirobifluorene, a thiophene, a furan, a phenyl group, an oligo-phenylenevinylene, and an oligofluorene.

14. The organic electroluminescent device according to claim 1, wherein the second organic layer is a light-emitting layer; and the light-emitting layer comprises a host and the second compound as a dopant.

15. The organic electroluminescent device according to claim 14, wherein the first organic layer is a hole injection layer, and the hole injection layer is positioned between the anode and the light-emitting layer.

16. The organic electroluminescent device according to claim 14, wherein the host is an anthracene-based compound, a fluorene-based compound or a diphenylene-based compound. compound.

17. A display assembly comprising the organic electroluminescent device according to any one of claims 1 to 16.

18. An illumination device comprising the organic electroluminescent element according to any one of claims 15 to 17.

19. A composition comprising a first compound and a second compound, wherein the first compound has a general structure represented by Formula I: wherein, each of X, Y is independently selected from NR’, CR”R’”, O, S, or Se; said Z 1 , Z 2 each independently is selected from O, S or Se; said R 1 , R 2 , R', R", R'" are each independently selected from any one or a combination of more than one of hydrogen, deuterium, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, boryl, sulfinyl, sulfonyl, phosphinyl, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms; R 1 , R 2 may be the same or different, and at least one of R 1 , R 2 , R', R", R'" has an electron withdrawing group; the electron-withdrawing group is selected from the group consisting of halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, SCN, OCN, SF5, boryl, sulfinyl, sulfonyl, phosphinyl, azaheteroaromatic ring group, and any one or combination of alkyl group having 1 to 20 carbon atoms, cycloalkyl group having 3 to 20 ring carbon atoms, heteroalkyl group having 1 to 20 carbon atoms, aralkyl group having 7 to 30 carbon atoms, alkoxy group having 1 to 20 carbon atoms, aryloxy group having 6 to 30 carbon atoms, alkenyl group having 2 to 20 carbon atoms, alkynyl group having 2 to 20 carbon atoms, aryl group having 6 to 30 carbon atoms, heteroaryl group having 3 to 30 carbon atoms, alkylsilyl group having 3 to 20 carbon atoms, arylsilyl group having 6 to 20 carbon atoms, substituted with any one or more of halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, SCN, OCN, SF5, boryl, sulfinyl, sulfonyl, phosphinyl, azaheteroaromatic ring group; R in the formula I 1 , R 2 , R', R", R'" can be arbitrarily bonded to each other into a ring through a linking group or a single bond; the second compound has a general structure as shown in Formula II: wherein W is selected from O or S; said X 1 and X 2 each independently is selected from O, S or NR 3 ; Z 3 , Z 4 , Z 5 are each independently selected from N or CR 4 ; ring A, ring B are each independently selected from substituted or unsubstituted aryl ring having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl ring having 2 to 30 carbon atoms, substituted or unsubstituted cycloalkyl ring having 6 to 30 carbon atoms, substituted or unsubstituted heteroalkyl ring having 2 to 30 carbon atoms; said R 3 , R 4 each independently is selected from any one or a combination of more than one of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group with 3 to 20 carbon atoms, substituted or unsubstituted heteroalkyl group with 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl group with 3 to 20 carbon atoms, substituted or unsubstituted aralkyl group with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy group with 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group with 6 to 30 carbon atoms, substituted or unsubstituted alkylthio group with 1 to 20 carbon atoms, substituted or unsubstituted arylthio group with 6 to 30 carbon atoms, substituted or unsubstituted alkenyl group with 2 to 20 carbon atoms, substituted or unsubstituted alkynyl group with 2 to 20 carbon atoms, substituted or unsubstituted aryl group with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group with 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group with 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group with 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl group with 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl group with 6 to 20 carbon atoms, substituted or unsubstituted amino group, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxyl group, mercapto group, sulfinyl group, sulfonyl group, phosphino group; The ring A, the ring B and R 3 in the formula II can be arbitrarily bonded to each other into a ring through a linking group or a single bond. 4 in the formula II can be arbitrarily bonded to each other into a ring through a linking group or a single bond.

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