An organic electroluminescent device

Abstract

Disclosed is an organic electroluminescent device. The organic electroluminescent device comprises an anode, a cathode and an organic layer disposed between the anode and the cathode, the organic layer comprising a first organic layer, the first organic layer comprising a first organic material and a second organic material satisfying certain energy level requirements, and the conductivity of the first organic layer being greater than 3*10 ‑5 S / m. The novel organic electroluminescent device effectively regulates the hole injection capability, so that the comprehensive performance of the device is effectively improved. Also disclosed are an organic electroluminescent device and a first organic electroluminescent device.

Description

TECHNICAL FIELD

[0001] The present application relates to an organic electronic device, such as an organic electroluminescent device. More particularly, it relates to an organic electroluminescent device having a first organic layer comprising a first organic material and a second organic material fulfilling specific energetic requirements, and the electrical conductivity of the first organic layer is ≥ 3*10 -5 S / m. 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 plasma display devices.

[0003] An organic electroluminescent device (OLED) is composed of a cathode, an anode and a stack of organic light emitting materials between the cathode and anode, which converts electrical energy into light by applying a voltage across the device, with the advantages of wide viewing angle, high contrast and faster response time. Tang and Van Slyke at Kodak reported an organic light emitting device in 1987, with an arylamine hole-transporting layer and a tris-8-hydroxyquinoline-aluminum layer as the electron-transporting and light-emitting layer (Applied Physics Letters, 1987, 51(12): 913-915). After applying a voltage across the device, green light was emitted from the device, which laid the foundation for the development of modern organic light emitting diodes (OLEDs). The most advanced 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 a self-emitting solid-state device, they offer great potential for display and lighting applications. In addition, the inherent properties of organic materials, such as their flexibility, can make them very suitable for special applications, such as production on flexible substrates. OLEDs have the advantages of low cost, low power consumption, high brightness, wide viewing angle, thin thickness, etc. After decades of development, they have been widely used in display and lighting fields.

[0004] OLEDs can be categorized into three different types according to their light emission mechanism. OLED invented by Tang and van Slyke is fluorescent OLED. 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 OLED 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 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 triplet to singlet states. 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 molecule refers to any organic or organometallic material that is not a polymer. The molecular weight of small molecules can be quite large as long as it has a well-defined structure. 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 usually 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] OLED devices are generally composed of a stack of multiple organic functional layers, including hole injection layer (HIL), hole transport layer (HTL), electron blocking layer (EBL), hole blocking layer (HBL), electron transport layer (ETL), electron injection layer (EIL), etc. in addition to the emission layer (EML). The hole injection layer and the electron injection layer inject holes and electrons into the device from the anode and cathode terminals, respectively. The two carriers then migrate to the emission layer through the transport layers, recombine to form excitons, and emit light during the process of returning to the ground state from the excited state. Thus, the light emission is achieved.

[0008] Effective recombination of electrons and holes is an important factor affecting the light-emitting quantum efficiency of a device. Current methods for improving carrier balance in OLED devices mainly fall into three categories: 1) using appropriate electron and hole injection materials to balance the injected carriers, 2) improving electron and hole transport materials to change the transport ability of carriers in the organic transport material to achieve balance, and 3) improving the device structure to achieve carrier balance. The organic hole transport layer material (HTM) in existing OLED devices is mostly aromatic amine compounds, which have strong electron-donating ability and thus can achieve good hole injection. On the electron injection and transport side, there are relatively few types of organic materials available. Assuming that the electron and hole concentrations injected from the cathode and anode are the same, the hole mobility (10 -6 ~ 10 -4 cm 2 / Vs) is 1-3 orders of magnitude higher than the electron mobility (10 -5 ~ 10 -3 cm 2 / Vs), i.e., the hole concentration transported to the light-emitting layer is much higher than the electron concentration, resulting in unbalanced carrier concentration. Carrier imbalance not only easily causes carriers to accumulate at the interface of the film layer, generates heat, accelerates device aging, and reduces the service life, but also reduces the recombination probability of excitons, resulting in a decrease in device efficiency. Therefore, effectively slowing down the arrival of holes in the light-emitting region is an effective way to improve device efficiency.

[0009] To regulate the hole injection ability, M. A. Abkowitz et al. studied and compared the hole injection ability from ITO to the hole transport layer NPB and the hole injection ability after adding a layer of CuPc of different thickness between ITO and NPB in their paper (J. Phys. Chem. B 2000, 104, 3948-3952). They found that the introduction of CuPc weakened the hole injection ability of the device, but the efficiency of the corresponding device was significantly improved, and the voltage of the device was also increased. M. A. Abkowitz et al. believed that this was because the reduction of hole injection ability could better balance the carriers, i.e., the number of holes reaching the light-emitting region would be relatively reduced, thus improving the device efficiency. However, since CuPc was used to inhibit the efficiency of hole injection, although the device efficiency was improved, the device voltage was also sharply increased. In practical applications, too high a voltage will increase the power consumption of the device, and the process is too complex.

[0010] The hole injection layer (HIL) in the existing OLED device generally uses a hole transport material (HTM) doped with a proper amount of a P-type conductive dopant (PD) to regulate the hole injection capability, so as to realize the ohmic contact between the anode and the HIL layer. The conductivity of the HIL can reflect the strength of the hole injection capability to a certain extent, and the conductivity of the thin film and the hole injection capability of the HIL are generally controlled by selecting a suitable p-type conductive dopant and adjusting the doping proportion. The commonly used p-type conductive dopant is an organic material, for example, TWI330047 discloses a HTM:PD combination, and the conductivity of the p-type doped HIL ranges from 10 -6 ~1S / m. However, in the current research, the LUMO level of the p-type conductive dopant and the HOMO level of the hole transport material are relatively small, so that a high-conductivity HIL can be obtained under the condition of a low doping concentration (for example, 1-3wt%). The excessively high conductivity is easy to intensify the imbalance between holes and electrons, which is not conducive to the improvement of the device performance, and on the other hand, the lower amount of the p-type dopant is also difficult to accurately control in the device preparation process, thereby being difficult to regulate the conductivity of the HIL. SUMMARY

[0011] The present application aims to provide a novel organic electroluminescent device to solve at least part of the above problems. The novel organic electroluminescent device comprises an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a first organic layer, the first organic layer comprises a first organic material and a second organic material, and the conductivity of the first organic layer is ≥3*10 -5 S / m. The novel organic electroluminescent device effectively regulates the hole injection capability, so that the comprehensive performance of the device is effectively improved.

[0012] According to one embodiment of the present application, an organic electroluminescent device is disclosed, which comprises:

[0013] an anode, a cathode, and an organic layer disposed between the anode and the cathode;

[0014] wherein the organic layer comprises a first organic layer, and the first organic layer comprises a first organic material and a second organic material;

[0015] the LUMO level of the first organic material is LUMO 第一有机材料 , the HOMO level of the second organic material is HOMO 第二有机材料 , and the HOMO 第二有机材料 ≤-5.1eV, and LUMO 第一有机材料 -HOMO 第二有机材料 ≥0.3eV;

[0016] the conductivity of the first organic layer is ≥3*10-5 S / m.

[0017] According to another embodiment of the present application, an organic electroluminescence device is also disclosed, which comprises:

[0018] an anode, a cathode, and an organic layer disposed between the anode and the cathode;

[0019] wherein the organic layer comprises a first organic layer, the first organic layer comprises a first organic material and a second organic material, and the LUMO energy level of the first organic material is LUMO 第一有机材料 , the HOMO energy level of the second organic material is HOMO 第二有机材料 , and the LUMO 第一有机材料 -HOMO 第二有机材料 ≥ 0.3 eV, the electrical conductivity of the first organic layer is ≥ 3*10 - 5 S / m, and the second organic material has a structure represented by formula H:

[0020]

[0021] In formula H,

[0022] Ar1, Ar2, and Ar3 are the same or different at each occurrence and are selected from a substituted or unsubstituted aryl group having 6-30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3-30 carbon atoms;

[0023] when Ar1, Ar2and Ar3are the same or different at each occurrence selected from substituted aryl having 6-30 carbon atoms, or substituted heteroaryl having 3-30 carbon atoms, the aryl or heteroaryl is substituted with one or more groups selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclyl having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilicon having 3-20 carbon atoms, substituted or unsubstituted arylsilicon having 6-20 carbon atoms, substituted or unsubstituted alkyl germanium having 3-20 carbon atoms, substituted or unsubstituted aryl germanium having 6-20 carbon atoms, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0024] neighboring substituents Ar1, Ar2and Ar3are optionally linked to form a ring.

[0025] According to another embodiment of the present application, a first organic electroluminescent device is also disclosed, comprising:

[0026] an anode, a cathode, and an organic layer disposed between the anode and the cathode;

[0027] wherein the organic layer comprises a first organic layer, the first organic layer is in contact with the anode, and comprises a first organic material and a second organic material;

[0028] the electrical conductivity of the first organic layer is ≥ 3*10 -5 S / m;

[0029] the efficiency voltage ratio η of the first organic electroluminescent device under the same current density is greater than or equal to 104% of the η of a second organic electroluminescent device; wherein the is the ratio of allowed excitons in quantum mechanics; the device structure of the second organic electroluminescent device is the same as that of the first organic electroluminescent device, except for the following differences: the organic layer in contact with the anode in the second organic electroluminescent device is a third organic layer and contains a third organic material and a fourth organic material, and the materials in at least one of the two groups of materials, the first organic material and the third organic material, the second organic material and the fourth organic material, are the same;

[0030] and the third organic layer in the second organic electroluminescent device at least meets one of the following conditions:

[0031] 1) the HOMO energy level of the fourth organic material is HOMO 第四有机材料 , and HOMO 第四有机材料 -5.1 eV;

[0032] 2) the LUMO energy level of the third organic material is LUMO 第三有机材料 , the HOMO energy level of the fourth organic material is HOMO 第四有机材料 , and LUMO 第三有机材料 -HOMO 第四有机材料 <0.3 eV;

[0033] 3) the conductivity of the third organic layer is less than 3*10 -5 S / m.

[0034] The novel organic electroluminescent device disclosed in the present application comprises an anode, a cathode and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a first organic layer, the first organic layer comprises a first organic material and a second organic material meeting certain energy level requirements, and the conductivity of the first organic layer is ≥ 3*10 -5 S / m. The novel organic electroluminescent device effectively regulates the hole injection capability, so that the comprehensive performance of the device is effectively improved. BRIEF DESCRIPTION OF DRAWINGS

[0035] Figure 1 is a schematic diagram of an organic light emitting device which can comprise the organic electroluminescent device of the present application;

[0036] Figure 2 is another schematic diagram of an organic light emitting device which can comprise the organic electroluminescent device of the present application;

[0037] Figure 3 is a trend curve graph of the conductivity of an organic thin film formed by compound 1-2 and compound HT-7 varying with the doping ratio of compound 1-2;

[0038] Figure 4is a graph showing the tendency of the conductivity of an organic thin film formed from compound 3-2 and compound HT-7 to change with the doping ratio of compound 3-2. DETAILED DESCRIPTION

[0039] OLEDs can be fabricated on a variety of substrates, such as glass, plastic, and metal. Figure 1 An illustrative, non-limiting organic light emitting device 100 is shown. The figures are not necessarily drawn to scale, and some layer structures can be omitted as desired. 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. Device 100 can be fabricated by sequentially depositing the layers described. The properties and functions of the various layers and exemplary materials are described in more detail in U.S. Patent No. 7,279,704 B2, columns 6-10, which is incorporated by reference in its entirety.

[0040] There are many more examples of each of these layers. 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 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 entireties, disclose examples of cathodes, including composite cathodes having a thin layer of a metal such as Mg:Ag overlying a transparent, conductive, sputter-deposited ITO layer. The principles and use of blocking layers 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 entireties. 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.

[0041] The above-described layered structure is provided by way of non-limiting example. The functionality 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 the best performance. Any functional layer can include several sub-layers. For example, an emissive layer can have two layers of different emissive materials to achieve a desired emission spectrum.

[0042] In one embodiment, an OLED can be described as having a "layer" disposed between the cathode and anode. The layer can include one or more layers.

[0043] 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 1 Instead, the cathode 190 can also include an encapsulation layer 102 on top to prevent harmful substances 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 by reference herein in its entirety.

[0044] Devices made according to embodiments of the application can be incorporated into a variety of consumer products having one or more electronic component modules (or units) of the devices. Some examples of these consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor illumination and / or signaling, head-up displays, fully or partially transparent displays, flexible displays, smartphones, tablet computers, phablets, wearable devices, smartwatches, laptop computers, digital cameras, camcorders, viewfinders, micro-displays, 3-D displays, vehicle displays and tail lights.

[0045] The materials and structures described herein can also be used in other organic electronic devices listed above.

[0046] 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 than the second layer. Unless specified that the first layer is "in contact with" the second layer, other layers can be 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.

[0047] 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.

[0048] A ligand can be termed "photosensitizing" when it is believed to directly contribute to the photoactive properties of the emissive material. A ligand can be termed "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 photosensitizing ligand.

[0049] 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 generally be divided into two types, P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence results from triplet-triplet annihilation (TTA).

[0050] On the other hand, E-type delayed fluorescence does not rely on the collision of two triplets, but rather on the conversion between a triplet and a singlet excited state. A compound capable of E-type delayed fluorescence needs to have a small singlet-triplet energy gap in order for the conversion between states to be possible. Thermal energy can activate the transition from triplet back to singlet. This type of delayed fluorescence is also known as 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, then the fraction of singlet excited states that are refilled can reach 75%. The total singlet fraction can be 100%, far exceeding the spin-statistics limit of 25% for electrically generated excitons.

[0051] E-type delayed fluorescence characteristics can be seen 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 (ΔE S-T ). Organic non-metal-containing donor-acceptor light-emitting materials can be able to achieve this. The emission of 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 small ΔE S-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).

[0052] In this context, the HOMO level (highest occupied molecular orbital) and LUMO level (lowest unoccupied molecular orbital) of an organic material are measured using cyclic voltammetry. In this context, all "HOMO levels" and "LUMO levels" are expressed as negative values, with smaller values (i.e. larger absolute values) indicating deeper levels. In this context, the expression "HOMO level of the second organic material ≤ -5.1 eV" means that the HOMO level of the second organic material is equal to -5.1 eV or more negative, e.g. -5.13 eV. In this context, the difference between the LUMO level of the first organic material (p-type doped material, PD) and the HOMO level of the second organic material (hole-transport material, HTM) is defined as LUMO PD - HOMO HTM Since the HOMO level of a typical transport material is deeper, this difference is positive.

[0053] In this context, the HOMO level of the HTM in the HIL and / or HTL is ≤ -5.1 eV in order to have the desired effect. In OLED devices, the HOMO level of the host material is typically -5.4 eV or deeper, and therefore it is desirable for the HOMO level of the HTM to be deeper in order to better match the host material. Furthermore, due to their structure, the HOMO levels of currently available HTMs are typically not less than -5.9 eV, i.e. ≥ -5.9 eV.

[0054] The term "hole injection ability" refers to the efficiency of hole injection from the anode into the organic layer in a device, which can be measured by electrical conductivity.

[0055] The term "electrical conductivity" refers to the electrical conductivity of a given film, which is measured by depositing the material to be tested in a high vacuum (e.g. 10 -6 Torr) in a predetermined doping ratio by co-evaporation onto a test substrate having an aluminum electrode, and forming a test region having a thickness of 100 nm, a length of 6 mm and a width of 1 mm, and then measuring the resistance of this region by applying a voltage across the electrodes at room temperature, and then calculating the electrical conductivity of the given film according to Ohm's law and the geometric dimensions. Note that even if the HTM and PD materials are kept constant, i.e. the difference between the energy levels is constant, the hole injection ability can be adjusted to some extent by adjusting the doping ratio. Since the electrical conductivity of an organic semiconductor film is directly related to the material and doping ratio used to form the film, the electrical conductivity of an organic film formed from two or more organic materials having a given structure in a given doping ratio is determined. In the present study, the electrical conductivity of the organic layer formed from the first organic material and the second organic material having a given structure in a given doping ratio was measured by the above method.

[0056] The term "doping ratio" refers to the percentage of one material in the total mass of the organic thin film.

[0057] Figure 3 The trend curve of the conductivity of the organic thin film formed by compound 1-2 and compound HT-7 is shown, the LUMO energy level of compound 1-2 and the HOMO energy level difference of HT-7 is 0.5 eV, and as the doping ratio of compound 1-2 increases, the conductivity of the obtained organic layer also increases: when the doping ratio of compound 1-2 is 0%, the conductivity of the obtained organic layer is 8.1*10 -6 S / m; when the doping ratio of compound 1-2 is 3%, the conductivity of the obtained organic layer is 2.4*10 -5 S / m; when the doping ratio of compound 1-2 is 20%, the conductivity of the obtained organic layer is 8.9*10 -4 S / m; when the doping ratio of compound 1-2 is 25%, the conductivity of the obtained organic layer is 9.2*10 -4 S / m. It can be seen that when the doping ratio of compound 1-2 is 20%-25%, the conductivity of the obtained organic layer is basically stable, which is two orders of magnitude higher than that of the un-doped. Therefore, the conductivity of the obtained organic layer can be effectively adjusted by adjusting the doping ratio of compound 1-2, so that the conductivity of the obtained organic layer is ≥3*10 -5 S / m.

[0058] Figure 4 The trend curve of the conductivity of the organic thin film formed by compound 3-2 and compound HT-7 is shown, the LUMO energy level of compound 3-2 and the HOMO energy level difference of HT-7 is 0.33 eV, and as the doping ratio of compound 3-2 increases, the conductivity of the obtained organic layer also increases: when the doping ratio of compound 3-2 is 2%, the conductivity of the obtained organic layer is 2.6*10 -5 S / m; when the doping ratio of compound 3-2 is 3%, the conductivity of the obtained organic layer is 8.0*10 -5 S / m; when the doping ratio of compound 3-2 is 5%, the conductivity of the obtained organic layer is 3.9*10 -4 S / m. Similarly, the conductivity of the obtained organic layer can be effectively adjusted by adjusting the doping ratio of compound 3-2, so that the conductivity of the obtained organic layer is ≥3*10 -5 S / m.

[0059] Generally speaking, in an OLED device, as the doping ratio of the p-type conductive doping material (PD) in the HIL increases, the conductivity of the HIL also increases, but for an OLED device, the conductivity range is 3*10 -5S / m ~ 1*10 -2 S / m, the conductivity is too low, affecting the hole injection, making the device voltage rise, thereby increasing the power consumption, the conductivity is too high, easy to cause the display in the horizontal crosstalk effect, and the conductivity is too high, often means that the PD doping concentration is too high, at this time it is possible to cause carrier accumulation and lead to device life decline, and also greatly improve the device preparation cost.

[0060] When the device is applied with a forward bias, the current begins to flow through the device, when the voltage reaches the starting voltage of the device, the device begins to emit light, therefore, the lower the voltage under the same current density, the smaller the power consumption of the device.

[0061] The "EQE (External Quantum Efficiency)" of the OLED device refers to the ratio of the number of photons emitted from the surface of the device to the number of injected electrons in the observation direction. Since OLED belongs to current driving (electrons and holes are injected and then combined), EQE can be used to reflect the good or bad of the OLED light emitting mechanism to some extent. It should be noted that blindly pursuing high EQE is not the first choice in the industry, and more importantly, the overall performance of the device under the influence of EQE, voltage, life and other factors should be comprehensively considered.

[0062] The OLED device in this paper uses the instrument provided by Suzhou Fosd Scientific Instruments Co., Ltd. with model FS-1000GA3 to perform I-V-L (current-voltage-brightness) photoelectric property test. The EQE of the device is calculated by the built-in formula as follows:

[0063]

[0064]

[0065] Among them, LightingArea is the light emitting area of the device, Current is the current, which is measured by Keithley2400, and the unit is ampere (A).

[0066] Photorad (radiation intensity) is obtained by multiplying the radiation intensity value at each wavelength from 380nm to 780nm by the wavelength and then summing up, and the radiation intensity is measured by the built-in spectrometer of the spectrometer FS-1000GA3.

[0067] Definitions of substituent terms

[0068] Halogen or halide - as used herein, includes fluorine, chlorine, bromine and iodine.

[0069] Alkyl - As used herein, includes straight-chain and branched-chain alkyl groups. Alkyl groups can be alkyl groups having 1 to 20 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. In addition, alkyl groups can be optionally substituted.

[0070] Cycloalkyl - As used herein includes cyclic alkyl groups. Cycloalkyl groups can be cycloalkyl groups having 3 to 20 ring carbon atoms, preferably cycloalkyl groups having 4 to 10 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. In addition, cycloalkyl groups can be optionally substituted.

[0071] Heteroalkyl - As used herein, heteroalkyl groups include alkyl chains in which one or more carbons is replaced with a heteroatom selected from the group consisting of nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium, and boron atoms. Heteroalkyl groups can be heteroalkyl groups having 1 to 20 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, triethylgermylmethyl, triethylgermylethyl, triisopropylgermylmethyl, triisopropylgermylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl, triisopropylsilylethyl. In addition, heteroalkyl groups can be optionally substituted.

[0072] Alkenyl - As used herein, encompasses straight-chain, branched-chain, and cyclic alkenyl groups. Alkenyl groups can be alkenyl groups containing 2 to 20 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-buten- dienyl, 1 -methyl-ethenyl, phenethenyl, 2,2-diphenylethenyl, 1,2-diphenylethenyl, 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.

[0073] Alkynyl - As used herein, encompasses straight-chain alkynyl groups. Alkynyl groups can be alkynyl groups containing 2 to 20 carbon atoms, preferably alkynyl groups 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, phenylacetylenyl, phenylpropynyl, and the like. Of the above, ethynyl, propynyl, propargyl, 1 -butynyl, 2-butynyl, 3-butynyl, 1 -pentynyl, and phenylacetylenyl are preferred. Additionally, the alkynyl group can be optionally substituted.

[0074] Aryl or aromatic - As used herein, both non-fused and fused systems are contemplated. Aryl groups can be aryl groups having 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms, more preferably aryl groups having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthyl, anthryl, azulenyl, phenanthryl, fluorenyl, pyrenyl, perylenyl, and azulenylenyl, 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.

[0075] ​Heterocyclyl or heterocycle - as used herein, non-aromatic cyclic groups are contemplated. Non-aromatic heterocyclyl groups include saturated heterocyclic groups having 3-20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3-20 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. Preferred non-aromatic heterocyclyl groups are those having 3 to 7 ring atoms, which include 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, oxepanyl, thiepanyl, azepanyl and tetrahydrothiopyranyl. Additionally, the heterocyclyl group can be optionally substituted.

[0076] Heteroaryl - as used herein, non-fused and fused heteroaromatic groups containing 1 to 5 heteroatoms, wherein at least one heteroatom 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. Heteroaryl also refers to heteroaromatic. Heteroaryl groups can be heteroaryl groups having 3 to 30 carbon atoms, preferably heteroaryl groups having 3 to 20 carbon atoms, more preferably heteroaryl groups having 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indolizine, benzoxazole, benzoisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phtalazine, pteridine, xanthene, acridine, phenoxazine, phenothiazine, benzofuro[3,2-d]pyridine, furo[3,2-d]dipyridine, benzothieno[3,2-d]pyridine, thieno[3,2-d]dipyridine, benzoselenopheno[3,2-d]pyridine, selenopheno[3,2-d]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.

[0077] Alkoxy - as used herein, is 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. In addition, the alkoxy group can be optionally substituted.

[0078] Aryloxy - as used herein, is 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. In addition, the aryloxy group can be optionally substituted.

[0079] Arylalkyl - as used herein, encompasses an aryl-substituted alkyl group. The arylalkyl group can be an arylalkyl group having 7 to 30 carbon atoms, preferably an arylalkyl group having 7 to 20 carbon atoms, more preferably an arylalkyl group having 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 above, benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, and 2-phenylisopropyl are preferred. In addition, the arylalkyl group can be optionally substituted.

[0080] Alkylsilyl groups - as used herein, encompass alkyl-substituted silyl groups. Alkylsilyl groups can be alkylsilyl groups having 3-20 carbon atoms, preferably alkylsilyl groups having 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 groups can be optionally substituted.

[0081] Arylsilyl groups - as used herein, encompass at least one aryl-substituted silyl group. Arylsilyl groups can be arylsilyl groups having 6-30 carbon atoms, preferably arylsilyl groups having 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 groups can be optionally substituted.

[0082] Alkylgermanyl groups - as used herein, encompass alkyl-substituted germanyl groups. Alkylgermanyl groups can be alkylgermanyl groups having 3-20 carbon atoms, preferably alkylgermanyl groups having 3 to 10 carbon atoms. Examples of alkylgermanyl groups include trimethylgermanyl, triethylgermanyl, methyldiethylgermanyl, ethyldimethylgermanyl, tripropylgermanyl, tributylgermanyl, triisopropylgermanyl, methyldiisopropylgermanyl, dimethylisopropylgermanyl, tri-t- butylgermanyl, triisobutylgermanyl, dimethyl-t-butylgermanyl, methyldi-t- butylgermanyl. Additionally, the alkylgermanyl groups can be optionally substituted.

[0083] Arylgermanyl groups - as used herein, encompass at least one aryl- or heteroaryl-substituted germanyl group. Arylgermanyl groups can be arylgermanyl groups having 6-30 carbon atoms, preferably arylgermanyl groups having 8 to 20 carbon atoms. Examples of arylgermanyl groups include triphenylgermanyl, phenyldiphenylgermanyl, diphenylphenylgermanyl, phenyldiethylgermanyl, diphenylethylgermanyl, phenyldimethylgermanyl, diphenylmethylgermanyl, phenyldiisopropylgermanyl, diphenylisopropylgermanyl, diphenylbutylgermanyl, diphenylisobutylgermanyl, diphenyl-t- butylgermanyl. Additionally, the arylgermanyl groups can be optionally substituted.

[0084] The term "aza" in aza-dibenzofurans, aza-dibenzothiophenes, and the like, refers to the replacement of one or more C-H groups in the corresponding aromatic fragment with a nitrogen atom. For example, aza-triphenylenes include dibenzo[f,h]quinoxalines, dibenzo[f,h]quinolines, and other analogs having two or more nitrogens in the ring system. Other nitrogen analogs of the aza derivatives described above will occur to those of ordinary skill in the art and all such analogs are intended to be encompassed by the terms described herein.

[0085] In the present disclosure, when any one 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 alkylsilyl, substituted arylsilyl, substituted alkylgermanyl, substituted arylgermanyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxylic acid, substituted ester, substituted sulfinyl, substituted sulfonyl, and substituted phosphine is used, unless otherwise defined, it is meant that any one of the alkyl, cycloalkyl, heteroalkyl, heterocyclyl, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermanyl, arylgermanyl, amino, acyl, carbonyl, carboxylic acid, ester, sulfinyl, sulfonyl, and phosphine groups can be substituted with one or more selected from the group consisting of deuterium, halogen, unsubstituted alkyl having 1-20 carbon atoms, unsubstituted cycloalkyl having 3-20 ring carbon atoms, unsubstituted heteroalkyl having 1-20 carbon atoms, unsubstituted heterocyclyl having 3-20 ring atoms, unsubstituted aralkyl having 7-30 carbon atoms, unsubstituted alkoxy having 1-20 carbon atoms, unsubstituted aryloxy having 6-30 carbon atoms, unsubstituted alkenyl having 2-20 carbon atoms, unsubstituted alkynyl having 2-20 carbon atoms, unsubstituted aryl having 6-30 carbon atoms, unsubstituted heteroaryl having 3-30 carbon atoms, unsubstituted alkylsilyl having 3-20 carbon atoms, unsubstituted arylsilyl having 6-20 carbon atoms, unsubstituted alkylgermanyl having 3-20 carbon atoms, unsubstituted arylgermanyl having 6-20 carbon atoms, unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphine, and combinations thereof.

[0086] It will be appreciated that when a molecular fragment is described as a substituent or otherwise attached to another moiety, it can be written by its name according to whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is an entire molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying a substituent or attached fragment are considered to be equivalent.

[0087] In the compounds mentioned in the present disclosure, hydrogen atoms can be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen can also be replaced by other stable isotopes thereof. The replacement of other stable isotopes in the compounds can be preferred due to its enhanced efficiency and stability of the device.

[0088] In the compounds mentioned in the present disclosure, poly-substitution refers to di-substitution and up to the maximum available substitution. When a substituent in the compounds mentioned in the present disclosure is indicated as poly-substitution (including di-substitution, tri-substitution, tetra-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.

[0089] 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.

[0090] 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:

[0091]

[0092] 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:

[0093]

[0094] 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:

[0095]

[0096] Further, the expression "adjacent substituents can optionally be joined to form a ring" is also intended to mean that, in case one of the two adjacent substituents represents hydrogen, the second substituent is bound at the position where the hydrogen atom is bound to, thus forming a ring. This is exemplified by the following formula:

[0097]

[0098] According to one embodiment of the present application, an organic electroluminescent device is disclosed, comprising:

[0099] an anode, a cathode, and an organic layer disposed between the anode and the cathode;

[0100] wherein the organic layer comprises a first organic layer, and the first organic layer comprises a first organic material and a second organic material;

[0101] the LUMO energy level of the first organic material is LUMO 第一有机材料 , the HOMO energy level of the second organic material is HOMO 第二有机材料 , and the HOMO 第二有机材料 ≤ -5.1 eV, and the LUMO 第一有机材料 - HOMO 第二有机材料 ≥ 0.3 eV;

[0102] the electrical conductivity of the first organic layer is ≥ 3 x 10 -5 S / m.

[0103] According to one embodiment of the present application, an organic electroluminescent device is disclosed, comprising:

[0104] an anode, a cathode, and an organic layer disposed between the anode and the cathode;

[0105] wherein the organic layer comprises a first organic layer, the first organic layer comprises a first organic material and a second organic material, and the LUMO energy level of the first organic material is LUMO 第一有机材料 , the HOMO energy level of the second organic material is HOMO 第二有机材料 , and the LUMO 第一有机材料 - HOMO 第二有机材料 ≥ 0.3 eV, the electrical conductivity of the first organic layer is ≥ 3 x 10 - 5 S / m, and the second organic material has a structure represented by formula H:

[0106]

[0107] In formula H,

[0108] Ar1, Ar2, and Ar3are the same or different at each occurrence and are selected from the group consisting of substituted or unsubstituted aryl having 6-30 carbon atoms, or substituted or unsubstituted heteroaryl having 3-30 carbon atoms;

[0109] When Ar1, Ar2, and Ar3are the same or different at each occurrence and are selected from the group consisting of substituted aryl having 6-30 carbon atoms, or substituted heteroaryl having 3-30 carbon atoms, the aryl or heteroaryl is substituted with one or more groups selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclyl having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl having 6-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0110] Adjacent substituents Ar1, Ar2, and Ar3are optionally linked to form a ring.

[0111] In the present embodiment, adjacent substituents Ar1, Ar2, and Ar3are optionally linked to form a ring, is intended to mean that any one or more of the groups of adjacent substituents, e.g., adjacent substituents Ar1and Ar2, adjacent substituents Ar1and Ar3, and adjacent substituents Ar2and Ar3, can be linked to form a ring. Obviously, it is also possible that none of these groups of adjacent substituents are linked to form a ring.

[0112] According to one embodiment of the present application, wherein the second organic material having a structure represented by formula H is a monoarylamine compound.

[0113] According to one embodiment of the present application, wherein the LUMO 第一有机材料 - HOMO 第二有机材料 ≥ 0.33 eV.

[0114] According to one embodiment of the present application, wherein the LUMO 第一有机材料 - HOMO第二有机材料 ≥ 0.4 eV.

[0115] According to one embodiment of the present application, wherein the LUMO 第一有机材料 - HOMO 第二有机材料 ≥ 0.45 eV.

[0116] According to one embodiment of the present application, wherein the HOMO 第二有机材料 ≤ -5.13 eV.

[0117] According to one embodiment of the present application, wherein the HOMO 第二有机材料 ≤ -5.2 eV.

[0118] According to one embodiment of the present application, wherein the electrical conductivity of the first organic layer is ≥ 5*10 -5 S / m.

[0119] According to one embodiment of the present application, wherein the electrical conductivity of the first organic layer is ≥ 7*10 -5 S / m.

[0120] According to one embodiment of the present application, wherein the electrical conductivity of the first organic layer is ≥ 10*10 -5 S / m.

[0121] According to one embodiment of the present application, wherein the electrical conductivity of the first organic layer is ≥ 30*10 -5 S / m.

[0122] According to one embodiment of the present application, wherein the electrical conductivity of the first organic layer is ≥ 50*10 -5 S / m.

[0123] According to one embodiment of the present application, wherein the first organic material is in a weight ratio of 0.1% to 90% of the first organic layer.

[0124] According to one embodiment of the present application, wherein the first organic material is in a weight ratio of 1% to 50% of the first organic layer.

[0125] According to one embodiment of the present application, wherein the first organic material is in a weight ratio of 2% to 30% of the first organic layer.

[0126] According to one embodiment of the present application, wherein the thickness of the first organic layer is 1-30 nm.

[0127] According to one embodiment of the present application, wherein the thickness of the first organic layer is 5-15 nm.

[0128] According to one embodiment of the present application, wherein, when the organic electroluminescent device emits red light, the organic electroluminescent device has an EQE no less than 22%, a voltage no higher than 4.5V under the condition of 15mA / cm 2 According to one embodiment of the present application, wherein, when the organic electroluminescent device emits red light, the organic electroluminescent device has an EQE no less than 22%, a voltage no higher than 4.5V under the condition of 15mA / cm 2 According to one embodiment of the present application, wherein, when the organic electroluminescent device emits red light, the organic electroluminescent device has an EQE no less than 22%, a voltage no higher than 4.5V under the condition of 15mA / cm 2 According to one embodiment of the present application, wherein, when the organic electroluminescent device emits red light, the organic electroluminescent device has an EQE no less than 22%, a voltage no higher than 4.5V under the condition of 15mA / cm

[0129] According to one embodiment of the present application, wherein, when the organic electroluminescent device emits red light, the organic electroluminescent device has an EQE no less than 22%, a voltage no higher than 4.5V under the condition of 15mA / cm 2 According to one embodiment of the present application, wherein, when the organic electroluminescent device emits red light, the organic electroluminescent device has an EQE no less than 22%, a voltage no higher than 4.5V under the condition of 15mA / cm 2 According to one embodiment of the present application, wherein, when the organic electroluminescent device emits red light, the organic electroluminescent device has an EQE no less than 22%, a voltage no higher than 4.5V under the condition of 15mA / cm 2 According to one embodiment of the present application, wherein, when the organic electroluminescent device emits red light, the organic electroluminescent device has an EQE no less than 22%, a voltage no higher than 4.5V under the condition of 15mA / cm

[0130] According to one embodiment of the present application, wherein, when the organic electroluminescent device emits red light, the organic electroluminescent device has an EQE no less than 22%, a voltage no higher than 4.5V under the condition of 15mA / cm 2 According to one embodiment of the present application, wherein, when the organic electroluminescent device emits red light, the organic electroluminescent device has an EQE no less than 22%, a voltage no higher than 4.5V under the condition of 15mA / cm 2 According to one embodiment of the present application, wherein, when the organic electroluminescent device emits red light, the organic electroluminescent device has an EQE no less than 22%, a voltage no higher than 4.5V under the condition of 15mA / cm 2 According to one embodiment of the present application, wherein, when the organic electroluminescent device emits red light, the organic electroluminescent device has an EQE no less than 22%, a voltage no higher than 4.5V under the condition of 15mA / cm

[0131] According to one embodiment of the present application, wherein, the first organic layer is in contact with the anode.

[0132] According to one embodiment of the present application, wherein, the organic electroluminescent device further comprises a second organic layer, and the second organic layer comprises a second organic material.

[0133] According to one embodiment of the present application, wherein, the thickness of the second organic layer is 10-200nm.

[0134] According to one embodiment of the present application, wherein, the second organic material is selected from:

[0135]

[0136] According to one embodiment of the present application, a first organic electroluminescent device is also disclosed, comprising:

[0137] an anode, a cathode, and an organic layer disposed between the anode and the cathode;

[0138] wherein the organic layer comprises a first organic layer, the first organic layer is in contact with the anode, and comprises a first organic material and a second organic material;

[0139] the electrical conductivity of the first organic layer is ≥ 3*10 -5 S / m;

[0140] the efficiency voltage ratio η of the first organic electroluminescent device under the same current density is greater than or equal to 104% of the η of a second organic electroluminescent device, wherein the is the proportion of allowed emitting excitons in quantum mechanics; the device structure of the second organic electroluminescent device is the same as that of the first organic electroluminescent device, except for the following differences: the organic layer in contact with the anode in the second organic electroluminescent device is a third organic layer and comprises a third organic material and a fourth organic material, and the materials of at least one of the two groups of materials, the first organic material and the third organic material, the second organic material and the fourth organic material, are the same;

[0141] and the third organic layer in the second organic electroluminescent device at least meets one of the following conditions:

[0142] 1) the HOMO energy level of the fourth organic material is HOMO 第四有机材料 , and HOMO 第四有机材料 -5.1 eV;

[0143] 2) the LUMO energy level of the third organic material is LUMO 第三有机材料 , the HOMO energy level of the fourth organic material is HOMO 第四有机材料 , LUMO 第三有机材料 -HOMO 第四有机材料 <0.3 eV;

[0144] 3) the electrical conductivity of the third organic layer is less than 3*10 -5 S / m.

[0145] According to one embodiment of the present application, wherein in the first organic electroluminescent device, the LUMO energy level of the first organic material is LUMO 第一有机材料 , the HOMO energy level of the second organic material is HOMO 第二有机材料 , and the LUMO 第一有机材料HOMO 第二有机材料 ≥ 0.3 eV.

[0146] According to one embodiment of the present application, wherein in the first organic electroluminescent device, the HOMO energy level of the second organic material is HOMO 第二有机材料 , and the HOMO 第二有机材料 ≤ -5.1 eV.

[0147] According to one embodiment of the present application, wherein the EQE of the first organic electroluminescent device is higher than 103% of the EQE of the second organic electroluminescent device under the same current density.

[0148] According to one embodiment of the present application, wherein the EQE of the first organic electroluminescent device is higher than 110% of the EQE of the second organic electroluminescent device under the same current density.

[0149] According to one embodiment of the present application, wherein the EQE of the first organic electroluminescent device is higher than 120% of the EQE of the second organic electroluminescent device under the same current density.

[0150] According to one embodiment of the present application, wherein the η of the first organic electroluminescent device is > 7.19 under the condition of 15 mA / cm 2 .

[0151] According to one embodiment of the present application, wherein the η of the first organic electroluminescent device is > 7.2 under the condition of 15 mA / cm 2 .

[0152] According to one embodiment of the present application, wherein the η of the first organic electroluminescent device is > 7.3 under the condition of 15 mA / cm 2 .

[0153] According to one embodiment of the present application, wherein the η of the first organic electroluminescent device is > 7.4 under the condition of 15 mA / cm 2 .

[0154] According to one embodiment of the present application, wherein the η of the first organic electroluminescent device is greater than or equal to 106% of the η of the second organic electroluminescent device under the same current density.

[0155] According to one embodiment of the present application, wherein the η of the first organic electroluminescent device is greater than or equal to 110% of the η of the second organic electroluminescent device under the same current density.

[0156] According to one embodiment of the present application, wherein the first organic electroluminescent device has an η that is greater than or equal to 120% of the η of the second organic electroluminescent device at the same current density.

[0157] According to one embodiment of the present application, wherein the first organic electroluminescent device has an η that is greater than or equal to 130% of the η of the second organic electroluminescent device at the same current density.

[0158] According to one embodiment of the present application, wherein the first organic material is a p-type conductive doped material; and the second organic material is a hole transport material.

[0159] According to one embodiment of the present application, wherein the first organic material has a structure represented by one of Formula 1 to Formula 3:

[0160]

[0161] In Formula 1, Formula 2 or Formula 3,

[0162] E is selected from N or CR1, the same or different at each occurrence;

[0163] X is selected from the group consisting of NR’, CR”R”’, O, S or Se, the same or different at each occurrence;

[0164] Ring A is, the same or different at each occurrence, a 5-membered heterocycle, and the 5-membered heterocycle contains one endocyclic double bond, at least one N atom and at least one Q;

[0165] Q is selected from O, S, Se and NR, the same or different at each occurrence; N consisting of;

[0166] R represents mono-substitution, poly-substitution or no substitution at each occurrence;

[0167] R, R1, R’, R”, R”’, R Nat 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, hydroxyl, thiol, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclyl having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl having 6-20 carbon atoms, and combinations thereof;

[0168] and at least one of the substituents R, R1, R', R" and R'" is a group having at least one electron withdrawing group;

[0169] adjacent substituents R, R', R", R'" can optionally be linked to form a ring.

[0170] In the present embodiment, adjacent substituents R, R', R", R'" can optionally be linked to form a ring, is intended to mean that any one or more of the groups of adjacent substituents, for example, adjacent substituents R, adjacent substituents R" and R'", adjacent substituents R and R", adjacent substituents R and R', and adjacent substituents R and R', of these groups of adjacent substituents can be linked to form a ring. Obviously, these adjacent substituents can also not be linked to form a ring.

[0171] According to one embodiment of the present application, wherein in Formula 2, the E is selected from CR1.

[0172] According to one embodiment of the present application, wherein the first organic material has a structure represented by Formula 1 or Formula 3.

[0173] According to one embodiment of the present application, wherein the first organic material has a structure represented by Formula 3-1:

[0174]

[0175] wherein X is, on each occurrence, the same or different, selected from NR', CR"R"', O, S, or Se;

[0176] at least one of R, R', R", and R'" is a group having at least one electron- withdrawing group;

[0177] Q is, on each occurrence, the same or different, selected from the group consisting of O, S, Se, and NR N ;

[0178] R, R', R", R'" and R N are, on each occurrence, 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, hydroxyl, thiol, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclyl having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl having 6-20 carbon atoms, and combinations thereof.

[0179] According to one embodiment of the present application, wherein in Formula 1, Formula 2, Formula 3, or Formula 3-1, X is, on each occurrence, the same or different, selected from CR"R'" or NR', and each of R', R", and R'" is a group having at least one electron- withdrawing group.

[0180] According to one embodiment of the present application, wherein in Formula 1, Formula 2, Formula 3, or Formula 3-1, X is, on each occurrence, the same or different, selected from CR"R'" or NR', and each of R', R", and R'" is a group having at least one electron- withdrawing group.

[0181] According to one embodiment of the present application, wherein in Formula 1, Formula 2, Formula 3, or Formula 3-1, X is, on each occurrence, the same or different, selected from the group consisting of:

[0182]

[0183] According to one embodiment of the present application, wherein in Formula 1, Formula 2, Formula 3, or Formula 3-1, the X is selected from X-1.

[0184] According to one embodiment of the present application, wherein in Formula 1, Formula 2, Formula 3, or Formula 3-1, Q is, at each occurrence, the same or different, selected from O or S.

[0185] According to one embodiment of the present application, wherein in Formula 1, Formula 2, Formula 3, or Formula 3-1, the R, R1, at 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 1-20 carbon atoms, unsubstituted cycloalkyl having 3-20 ring carbon atoms, unsubstituted alkoxy having 1-20 carbon atoms, unsubstituted alkenyl having 2-20 carbon atoms, unsubstituted aryl having 6-30 carbon atoms, unsubstituted heteroaryl having 3-30 carbon atoms, and any of alkyl having 1-20 carbon atoms, cycloalkyl having 3-20 ring carbon atoms, alkoxy having 1-20 carbon atoms, alkenyl having 2-20 carbon atoms, aryl having 6-30 carbon atoms, heteroaryl having 3-30 carbon atoms, and combinations thereof, 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.

[0186] According to one embodiment of the present application, wherein in Formula 1, Formula 2, Formula 3, or Formula 3-1, the R, R1, 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.

[0187] According to one embodiment of the present application, wherein the first organic material is selected from the group consisting of the following structures:

[0188]

[0189]

[0190]

[0191]

[0192] In combination with other materials

[0193] The materials described herein for specific layers in organic light emitting devices can be used in combination with a variety of other materials present in the device. The combinations of these materials are described in detail in US Patent Application US2016 / 0359122A1 at paragraphs 0132-0161, which is incorporated by reference herein in its entirety. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and the skilled person can readily consult the literature to identify other materials that can be used in combination.

[0194] The materials described herein for specific layers in organic light emitting devices can be used in combination with a variety of other materials present in the device. The combinations of these materials are described in detail in US Patent Application US2015 / 0349273A1 at paragraphs 0080-0101, which is incorporated by reference herein in its entirety. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and the skilled person can readily consult the literature to identify other materials that can be used in combination.

[0195] In embodiments of the device, the properties of the device are also tested using equipment conventional in the art, including but not limited to evaporation machines produced by Angstrom Engineering, optical testing systems, lifetime testing systems produced by Suzhou Fosdaxian, ellipsometers produced by Beijing Liangtuo, etc., using methods well known to those skilled in the art. Since those skilled in the art are all aware of the above-mentioned equipment use, testing methods and other related content, they can obtain the inherent data of the sample certainly and unaffectedly, therefore the above-mentioned related content will not be expanded in this patent.

[0196] The LUMO and HOMO energy levels of the materials in this paper were measured using cyclic voltammetry. The tests were conducted using a CorrTest CS120 electrochemical workstation manufactured by Wuhan CorrTest Instruments Co., Ltd., employing a three-electrode system: a platinum disk electrode as the working electrode, an Ag / AgNO3 electrode as the reference electrode, and a platinum wire electrode as the auxiliary electrode. Anhydrous DCM was used as the solvent, and 0.1 mol / L tetrabutylammonium hexafluorophosphate was used as the supporting electrolyte. The test compounds were prepared by adding 10... -3 For the mol / L solution, nitrogen gas was bubbled into the solution for 10 min to remove oxygen before the test. Instrument parameter settings: scan rate 100 mV / s, potential interval 0.5 mV, test window -1 V to 1 V.

[0197] The LUMO level of the first organic material and the HOMO level of the second organic material were tested using the cyclic voltammetry method described above. The conductivity of the organic layer composed of the first and second organic materials was also measured. The test samples HTM and PD materials were subjected to high vacuum (e.g., 10⁻⁶ ppm). -6 Torr was deposited onto a test substrate pre-prepared with aluminum electrodes using a co-evaporation method with a specific doping ratio, forming a test region with a thickness of 100 nm, a length of 6 mm, and a width of 1 mm. At room temperature, the resistance of this region was obtained by applying a voltage to the electrodes and measuring the current. The conductivity of the given thin film was then calculated based on Ohm's law and the geometric dimensions. Relevant data are shown in the table below.

[0198]

[0199] Device Examples

[0200] The following examples illustrate the working principle of this organic electroluminescence. Obviously, the following examples are for illustrative purposes only and are not intended to limit the scope of the invention. Based on the following examples, those skilled in the art can obtain other embodiments of the invention through modifications.

[0201] Examples 1-1 to 1-5 and Comparative Examples 1-1 to 1-5 are red phosphorescent light-emitting devices.

[0202] Example 1-1

[0203] The implementation method of Example 1-1 is as follows. First, the glass substrate is cleaned, which has... A thick indium tin oxide (ITO) anode was applied, followed by UV ozone and oxygen plasma treatment. The substrate was then dried in a nitrogen-filled glove box to remove moisture before being mounted on a substrate support and placed in a vacuum chamber. The vacuum level was approximately 10... -6 In the case of Torr, The organic layer was deposited sequentially on the ITO anode using a thermal vacuum process. First, HT-7 and compound 1-2 were co-deposited as a hole injection layer (HIL), with compound 1-2 comprising 20% ​​of the total weight of the HIL and a thickness of [missing information]. Subsequently, the vapor-deposited compound HT-7 was used as the hole transport layer (HTL), with a thickness of [missing information]. The vapor-deposited compound EB1 was used as an electron blocking layer (EBL) with a thickness of [missing information]. Next, red-emitting dopant compound D-1 was doped into the host compound RH to form a red-emitting layer (EML), wherein the doping ratio of compound D-1 was 2wt% and the thickness was [missing information]. Subsequently, compound HB1 was deposited as a hole blocking layer (HBL) with a thickness of [missing information]. On top of the HBL, co-deposited compounds ET and LiQ serve as an electron transport layer (ETL) with a thickness of [missing information]. LiQ accounts for 60% of the total weight of the ETL layer. On top of the ETL, vapor deposition... LiQ was used as the electron injection layer (EIL), and finally deposited by evaporation. Al was used as the cathode. The vapor-deposited device was transferred back to the glove box and sealed with a glass cover to complete the device.

[0204] Examples 1-2

[0205] The implementation methods of Examples 1-2 are the same as those of Examples 1-1, except that the doping ratio of compound 1-2 in HIL is adjusted to 25%.

[0206] Examples 1-3

[0207] The implementation methods of Examples 1-3 are the same as those of Example 1-1, except that in HIL, compound 1-2 is replaced with compound 3-2 and the doping ratio of compound 3-2 is adjusted to 3%.

[0208] Examples 1-4

[0209] The implementation methods of Examples 1-4 are the same as those of Examples 1-3, except that the doping ratio of compound 3-2 in HIL is adjusted to 5%.

[0210] Examples 1-5

[0211] The implementation methods of Examples 1-5 are the same as those of Examples 1-1, except that compound HT-12 is used instead of compound HT-7 in HIL and HTL.

[0212] Comparative Example 1-1

[0213] The implementation method of Comparative Example 1-1 is the same as that of Example 1-1, except that the doping ratio of compound 1-2 in HIL is adjusted to 3%.

[0214] Comparative Examples 1-2

[0215] The implementation methods of Comparative Examples 1-2 are the same as those of Examples 1-1, except that in HIL, compound PD-1 is used instead of compound 1-2 and the doping ratio of compound PD-1 is adjusted to 2%.

[0216] Comparative Examples 1-3

[0217] The implementation methods of Comparative Examples 1-3 are the same as those of Examples 1-3, except that the doping ratio of compound 3-2 in HIL is adjusted to 2%.

[0218] Comparative Examples 1-4

[0219] The implementation methods of Comparative Examples 1-4 are the same as those of Examples 1-1, except that compound HTM-A is used instead of compound HT-7 in HIL and HTL.

[0220] Comparative Examples 1-5

[0221] The implementation methods of Comparative Examples 1-5 are the same as those of Examples 1-1, except that compound HTM-B is used instead of compound HT-7 in HIL and HTL.

[0222] The partial device structures of Examples 1-1 to 1-5 and Comparative Examples 1-1 to 1-5 are shown in the table below, wherein HIL is obtained by doping with two compounds in the described weight ratio.

[0223] Table 1. Partial device structures of Examples 1-1 to 1-4 and Comparative Examples 1-1 to 1-3.

[0224]

[0225] The structure of the compound used in the device is shown below:

[0226]

[0227] The device performance of Examples 1-1 to 1-5 and Comparative Examples 1-1 to 1-5 was measured. Color coordinates (CIE), voltage, and external quantum efficiency (EQE) were measured at a current density of 15 mA / cm². 2 The η of the device is measured under the conditions of EQE and voltage and according to... All values ​​were calculated to be 1; the device lifetime (LT95) was calculated at 80 mA / cm. 2 The measured time for the brightness to decay to 95% of the initial brightness under constant current density driving is shown in Table 2.

[0228] Table 2 Device Data

[0229]

[0230]

[0231] From the color coordinates, it can be seen that the color coordinates of the embodiments and the comparative examples are consistent.

[0232] High EQE and low voltage OLED is a desirable good device. If the EQE of a device is high, the voltage is also high, then such a device is not desirable, for example, the EQE of comparative example 1-1 in Table 2 is as high as 33%, but the voltage is as high as 5.7V, while the EQE of example 1-1 is 31%, although it is 6% lower than comparative example 1-1, it is still a very high efficiency level, and the voltage of example 1-1 is only 3.8V, which is 50% lower than comparative example 1-1, so it can be seen that example 1-1 is an OLED device with excellent comprehensive performance, while comparative example 1-1 is not the OLED pursued in the industry.

[0233] According to the above analysis, the present application introduces the efficiency voltage ratio (η) parameter to reflect the comprehensive performance of the device, wherein is the proportion of allowed emitting excitons in quantum mechanics. In theory, the proportion of allowed emitting excitons in phosphorescent light emitting devices and thermally activated delayed fluorescence (TADF) devices is 100%, i.e. is 1; while the proportion of allowed emitting excitons in fluorescent light emitting devices is 25%, i.e. is 0.25. The larger the η, the lower the voltage and the higher the EQE of the device, and the better the comprehensive performance. Therefore, the η of the present application is greater than 7.19, which indicates that the device is an OLED device with excellent comprehensive performance. Taking example 1-1 as an example, EQE = 31%, V = 3.8V, example 1-1 is a phosphorescent light emitting device, so is 1, and η = 31 / (3.8*1) = 8.16, which is a device with excellent comprehensive performance.

[0234] As described above, examples 1-1 to 1-5 and comparative examples 1-1 to 1-5 are all phosphorescent light emitting devices, and the are all 1.

[0235] The same material is used in the HIL of example 1-1 and the HIL of comparative example 1-1, but in the HIL of comparative example 1-1, the doping ratio of compound 1-2 is 3%, and the conductivity of the HIL is only 2.4*10 -5S / m, the conductivity of the HIL is too low, which results in weak hole injection ability of the HIL, and the voltage of the device is sharply increased. Although the EQE of the comparative example 1-1 is as high as 33%, the η of the device is only 5.79, and the device still exhibits poor comprehensive performance. In addition, the weak hole injection ability of the HIL also brings negative effects on the stability of the device. On the contrary, in the HIL of the embodiment 1-1, the doping ratio of the compound 1-2 as the first organic material is 20%, and the conductivity of the HIL is 89*10 -5 S / m, which is greater than 3*10 -5 S / m. The use of the HIL can obtain a red light device with excellent comprehensive performance. The voltage of the device is only 3.8V at 15mA / cm 2 , the EQE reaches 31%, and the η reaches 8.16. In addition, the device lifetime (LT95) is 176h at 80mA / cm 2 , which is nearly 2 times of the device lifetime of the comparative example 1-1. Therefore, the present application can improve the comprehensive performance of the device by controlling the conductivity of the first organic layer to be greater than or equal to 3*10 -5 S / m.

[0236] In the HIL of the embodiment 1-2, the doping ratio of the compound 1-2 is increased to 25%, and the conductivity is increased to 92*10 -5 S / m, which further reduces the voltage of the device to 3.5V and improves the device lifetime to 184h. Although the EQE is slightly reduced to 27%, it is still at a very high level. More importantly, the η is 7.71, which exhibits more excellent comprehensive performance than the currently widely used device, such as the comparative example 1-2 (η is 7.14). In addition, in the HIL of the comparative example 1-2, the difference between the LUMO level of the compound PD-1 and the HOMO level of the compound HT-7 is only 0.09eV, which is far less than 0.30eV. Therefore, when the doping ratio of the compound PD-1 is 2%, the conductivity of the HIL reaches 110*10 -5 S / m. Although the HIL has good hole injection ability and high device performance, the difference between the LUMO level of the compound PD-1 and the HOMO level of the compound HT-7 in the HIL is only 0.09eV, which is less than 0.30eV, and is not conducive to the balance of the carriers in the device. On the contrary, the embodiment 1-2 further improves the device performance on the basis of the high level of the comparative example 1-2 by reasonably selecting the HIL material: the efficiency is increased by 8%, the lifetime is increased by 12%, and the voltage remains the same, which is very rare.

[0237] As can be seen from the above comparison, the present application selects the second organic material with a HOMO level ≤-5.1eV and a LUMO level greater than the HOMO 第二有机材料The first organic material with a high energy level of at least 0.3 eV is doped, and the conductivity of the HIL is effectively controlled by controlling the doping ratio of the first organic material, so that a red light device with excellent comprehensive performance as shown in Examples 1-1 and 1-2 can be obtained.

[0238] In the HIL of Example 1-3, the first organic material is compound 3-2, and the difference between the LUMO energy level of the first organic material and the HOMO energy level of the second organic material HT-7 is 0.33 eV, which is greater than 0.3 eV. In the HIL of Comparative Example 1-3, the doping ratio of compound 3-2 is 2%, and the conductivity of the HIL is 2.6*10 -5 S / m, which is less than 3*10 -5 S / m, and due to the low conductivity, it is difficult for holes to be injected from the anode to the HIL, so that the device voltage is high, the η is only 6.0, and the lifetime is short. In Example 1-3, by increasing the doping ratio of compound 3-2 to 3%, the conductivity of the HIL is 7.9*10 -5 S / m, which is greater than 3*10 -5 S / m; compared with Comparative Example 1-3, the voltage is reduced by 24% to 3.8V, the EQE remains at a very high level of 30%, and the lifetime is increased by 86%, so that a red light device with excellent comprehensive performance is obtained.

[0239] In Example 1-4, by increasing the doping ratio of compound 3-2 to 5%, the conductivity of the HIL is increased to 39*10 -5 S / m, so that the device voltage is further reduced to 3.5V, the device lifetime is increased to 172h, although the EQE is slightly reduced to 27%, it is still a very high level, and more importantly, the η is still 7.71, so that the comprehensive performance of this device is more excellent than that of the device as shown in Comparative Example 1-2 (η = 7.14) which is widely used at present, and the efficiency of Example 1-4 and Comparative Example 1-2 is increased by 8%, the lifetime is increased by 5%, and the voltage remains the same.

[0240] In summary, through the comparison of Examples 1-1 to 1-4 and Comparative Examples 1-1 to 1-3, it is proved that when the HOMO of the second organic material is ≤-5.1 eV, the LUMO 第一有机材料 -HOMO 第二有机材料 ≥0.3 eV, the conductivity of the first organic layer HIL is controlled by controlling the doping ratio of the first organic material, and when the conductivity of the first organic layer is ≥3*10 -5 S / m, a red light device with excellent comprehensive performance can be obtained.

[0241] Furthermore, the second organic materials used in Examples 1-1 and 1-5 are HT-7 and HT-12, respectively, with HOMO energy levels of -5.13 eV and -5.11 eV, both less than -5.1 eV; LUMO 化合物1-2 -HOMO HT-7 LUMO 化合物1-2 -HOMO HT-12 All are greater than 0.3 eV, and the conductivity of the first organic layer HIL is 8.9*10. -4 S / m, 2.4*10 -4 S / m are all greater than 3*10 -5 Therefore, the devices using the aforementioned HIL exhibit excellent overall performance at 15 mA / cm². 2 The voltages at these voltages were 3.8V and 3.9V, respectively, with EQE values ​​of 31% and 29%, and η values ​​of 8.16 and 7.44, demonstrating excellent overall performance at 80mA / cm. 2 The LT95 values ​​were 176 h and 153 h, respectively, demonstrating ultra-long device lifetimes. The second organic materials used in Comparative Examples 1-4 and 1-5 were HTM-A and HTM-B, respectively, with corresponding HOMO levels of -5.09 eV. Since the HOMO level is greater than -5.1 eV, even with LUMO... 化合物1-2 -HOMO HTM-A LUMO 化合物1-2 -HOMO HTM-B The energy level differences are all greater than 0.3 eV, and the electrical conductivity is all greater than 3*10. -5 The overall performance of the devices using the above-mentioned HIL is not ideal, with η being only 5.56 and 5.69 respectively. Although the EQE is not much different from that of Example 1-1, the voltage is higher, at 5.4V and 5.1V respectively, and the lifespan is only 28h and 61h respectively.

[0242] Examples 2-1 to 2-3 and Comparative Examples 2-1 to 2-3 are green phosphorescent light-emitting devices.

[0243] Example 2-1

[0244] The implementation method of Example 2-1 is as follows. First, the glass substrate is cleaned, which has... A thick indium tin oxide (ITO) anode was applied, followed by UV ozone and oxygen plasma treatment. The substrate was then dried in a nitrogen-filled glove box to remove moisture before being mounted on a substrate support and placed in a vacuum chamber. The vacuum level was approximately 10... -6 In the case of Torr, at a rate of 0.1 A / s by thermal vacuum sequentially on the ITO anode. First, a hole injection layer (HIL) was evaporated, which comprised HT-7 and compound 1-2, wherein compound 1-2 accounted for 20% of the total weight of the HIL, and the HIL had a thickness of Thereafter, compound HT-7 was evaporated as a hole transport layer (HTL) with a thickness of Compound EB2 was used as an electron blocking layer (EBL) with a thickness of Then, compound EB2, GH, and green light-emitting dopant D-2 were co-evaporated as an emitting layer (EML), wherein EB2, GH, and D-2 accounted for 48%, 48%, and 4% of the total weight of the EML, respectively, and the EML had a thickness of Subsequently, compound HB1 was evaporated as a hole blocking layer (HBL) with a thickness of On top of the HBL, compound ET and LiQ were co-evaporated as an electron transport layer (ETL) with a thickness of wherein LiQ accounted for 60% of the total weight of the ETL layer. On top of the ETL, compound LiQ was evaporated as an electron injection layer (EIL), and finally Al was evaporated as a cathode. The finished device was transferred back to the glove box and encapsulated with a glass cover to complete the device.

[0245] Example 2-2

[0246] Example 2-2 was implemented in the same way as Example 2-1, except that the doping ratio of compound 1-2 in the HIL was adjusted to 25%.

[0247] Example 2-3

[0248] Example 2-3 was implemented in the same way as Example 2-1, except that compound 3-2 was used instead of compound 1-2 in the HIL and the doping ratio of compound 3-2 was adjusted to 5%.

[0249] Comparative Example 2-1

[0250] Comparative Example 2-1 was implemented in the same way as Example 2-1, except that the doping ratio of compound 1-2 in the HIL was adjusted to 3%.

[0251] Comparative Example 2-2

[0252] Comparative Example 2-2 was implemented in the same way as Example 2-1, except that compound PD-1 was used instead of compound 1-2 in the HIL and the doping ratio of compound PD-1 was adjusted to 2%.

[0253] Comparative Example 2-3

[0254] The implementation methods of Comparative Examples 2-3 are the same as those of Examples 2-3, except that the doping ratio of compound 3-2 in HIL is adjusted to 2%.

[0255] The partial device structures of Examples 2-1 to 2-3 and Comparative Examples 1-1 to 1-3 are shown in the table below, wherein HIL is obtained by doping with two compounds in the recorded weight ratio.

[0256] Table 3. Partial device structures of Examples 2-1 to 2-3 and Comparative Examples 1-1 to 1-3.

[0257]

[0258] The structure of the new compound used in the device is shown below:

[0259]

[0260] The device performance of Examples 2-1 to 2-3 and Comparative Examples 2-1 to 2-3 was measured. Color coordinates (CIE), voltage, and external quantum efficiency (EQE) were measured at a current density of 15 mA / cm². 2 The η of the device is measured under the conditions of EQE and voltage and according to... All values ​​were calculated to be 1; the device lifetime (LT95) was calculated at 80 mA / cm. 2 The measured time for brightness to decay to 95% of the initial brightness under constant current density driving is shown in Table 4.

[0261] Table 4 Device Data

[0262]

[0263]

[0264] As can be seen from the color coordinates, the color coordinates of the shown embodiments are consistent with those of the comparative examples.

[0265] Examples 2-1 to 2-3 and Comparative Examples 2-1 to 2-3 are all phosphorescent light-emitting devices. All are 1.

[0266] The same materials were used in the HIL of Example 2-1 as in Comparative Example 2-1, but in the HIL of Comparative Example 2-1, the doping ratio of compound 1-2 was 3%, and the conductivity of the HIL was only 2.4 × 10⁻⁶. -5S / m, the conductivity of the HIL is too low, which results in weak hole injection ability of the HIL, and thus the device voltage is sharply increased. Although the EQE of the comparative example 2-1 is as high as 28%, the device η is only 5.71, and the device still exhibits poor comprehensive performance. In addition, the weak hole injection ability of the HIL also brings negative effects on the stability of the device. In contrast, in the HIL of the embodiment 2-1, the doping ratio of the compound 1-2 as the first organic material is 20%, and the conductivity of the HIL is 89*10 -5 S / m, which is greater than 3*10 -5 S / m. The green device using the HIL exhibits excellent comprehensive performance. The voltage is only 3.7V at 15mA / cm 2 , the EQE is as high as 27%, and the η is 7.30. In addition, the device lifetime (LT95) is 74h at 80mA / cm 2 , which is nearly 2 times of that of the device of the comparative example 2-1. Therefore, the comprehensive performance of the device can be improved by controlling the conductivity of the first organic layer to be greater than or equal to 3*10 -5 S / m.

[0267] In the embodiment 2-2, the doping ratio of the compound 1-2 is increased to 25%. Compared with the case where the doping ratio of the compound 1-2 is 20% in the embodiment 2-1, the conductivity of the HIL is slightly increased to 92*10 -5 S / m. Therefore, the device voltage is further decreased to 3.5V, and the device lifetime is increased to 86h. Although the EQE is slightly decreased to 26%, the η of the device is 7.43, which is more excellent than the comprehensive performance of the device shown in the comparative example 1-2 (η=6.86). In the comparative example 2-2, the first organic material is the compound PD-1, and the difference between the LUMO level and the HOMO level of the compound HT-7 is only 0.09eV, which is less than 0.30eV. When the doping ratio is 2%, the conductivity is as high as 110*10 -5 S / m. Although the HIL has good hole injection ability, and the device performance is high, the difference between the LUMO level of the compound PD-1 and the HOMO level of the compound HT-7 in the HIL is only 0.09eV, which is less than 0.30eV, and is not conducive to the balance of the carriers in the device. In contrast, the embodiment 2-2 further improves the device performance on the basis of the high level of the comparative example 2-2: the efficiency is increased by 8%, the lifetime is increased by 4%, and the voltage remains unchanged, which is very difficult.

[0268] As can be seen from the above comparison, in the present application, the second organic material with HOMO≤-5.1eV is selected in the first organic layer, and the difference between the LUMO level and the HOMO 第二有机材料A green light device with excellent overall performance is obtained by doping a first organic material with a doping level of at least 0.3 eV and effectively controlling the conductivity of the HIL by controlling the doping ratio of the first organic material.

[0269] In Examples 2-3, the first organic material is compound 3-2, whose LUMO energy level and the HOMO energy level of compound HT-7 have a difference of 0.33 eV, which is greater than 0.3 eV. The doping ratio of compound 3-2 is 5%, and the conductivity of HIL is 39*10. -5 S / m, greater than 3*10 -5 S / m. Using the above HIL, a green light device with excellent overall performance was obtained: at 15 mA / cm. 2 The voltage is only 3.4V, EQE is 25%, η is 7.35, and the voltage is 80mA / cm. 2 The device lifetime reached 95 hours (LT95). In contrast, Comparative Example 2-3, due to its lower conductivity, had difficulty injecting holes from the anode into the HIL, resulting in a higher device voltage, 43% higher than that of Example 2-3. Although reducing the conductivity of the HIL led to a slight increase in EQE, η was only 5.6. Furthermore, the difficulty in hole injection caused device instability. The lifetime of Example 2-3 was 239% longer than that of Comparative Example 2-3. Comparing Example 2-3 and Comparative Example 2-2, it was found that although the conductivity of Comparative Example 2-2 was greater than 3*10... -5 S / m, but since the energy level difference between the LUMO of compound PD-1 and the HOMO of HT-7 is 0.09 eV, which is less than 0.3 eV, both Examples 2-3 and Comparative Example 2-2 ensured hole injection. The voltages of the two were 3.4 V and 3.5 V, respectively, which were basically consistent. However, Example 2-3 was able to better balance the carriers, so the device efficiency was 4% higher than that of Comparative Example 2-2, and the lifetime was 34% longer.

[0270] In summary, the comparison between Examples 2-1 to 2-3 and Comparative Examples 2-1 to 2-3 demonstrates that the HOMO of the second organic material is ≤ -5.1 eV, and the LUMO is... 第一有机材料 -HOMO 第二有机材料 When the voltage is ≥0.3 eV, the conductivity of the first organic layer HIL is controlled by controlling the doping ratio of the first organic material. When the conductivity of the first organic layer is ≥3*10 -5 When the S / m ratio is low, a green light device with excellent overall performance can be obtained.

[0271] Examples 3-1 to 3-4 and Comparative Examples 3-1 to 3-3 are blue fluorescent light-emitting devices.

[0272] Example 3-1

[0273] The implementation method of Example 3-1 is as follows. First, the glass substrate is cleaned, which has... A thick indium tin oxide (ITO) anode was applied, followed by UV ozone and oxygen plasma treatment. The substrate was then dried in a nitrogen-filled glove box to remove moisture before being mounted on a substrate support and placed in a vacuum chamber. The vacuum level was approximately 10... -6 In the case of Torr, The organic layer was deposited sequentially on the ITO anode using a thermal vacuum process. First, a hole-injection layer (HIL) was deposited. The HIL contained HT-7 and compounds 1-2, with compounds 1-2 comprising 20% ​​of the total weight of the HIL. The HIL thickness was [missing information]. Subsequently, the vapor-deposited compound HT-7 was used as the hole transport layer (HTL), with a thickness of [missing information]. Compound HT-15 is used as an electron blocking layer (EBL) with a thickness of [missing information]. Then, blue dopant compound D-3 was co-deposited onto the blue host compound BH as the blue light emitting layer (EML), with a doping ratio of 4 wt% and a total thickness of [missing information]. Subsequently, compound HB2 was deposited as a hole blocking layer (HBL) with a thickness of [missing information]. On the HBL, co-deposited compounds ET and LiQ serve as the electron transport layer (ETL), with a thickness of [missing information]. LiQ accounts for 60% of the total weight of the ETL layer. It is deposited on top of the ETL layer. LiQ was used as the electron injection layer (EIL), and finally deposited by evaporation. Al was used as the cathode. The vapor-deposited device was transferred back to the glove box and sealed with a glass cover to complete the device.

[0274] Example 3-2

[0275] The implementation method of Example 3-2 is the same as that of Example 3-1, except that the doping ratio of compound 1-2 in HIL is adjusted to 30%.

[0276] Example 3-3

[0277] The implementation method of Example 3-3 is the same as that of Example 3-1, except that compound 1-2 is replaced by compound 3-2 in HIL and the doping ratio of compound 3-2 is adjusted to 10%.

[0278] Comparative Example 3-1

[0279] The implementation method of Comparative Example 3-1 is the same as that of Example 3-1, except that the doping ratio of compound 1-2 in HIL is adjusted to 3%.

[0280] Comparative Example 3-2

[0281] Example 3-2 was prepared in the same manner as Example 3-1, except that compound 1-2 was replaced with compound PD-1 in the HIL and the doping ratio of compound PD-1 was adjusted to 2%.

[0282] Comparative Example 3-3

[0283] Example 3-3 was prepared in the same manner as Example 3-3, except that the doping ratio of compound 3-2 in the HIL was adjusted to 2%.

[0284] The partial device structures of Examples 3-1 to 3-3 and Comparative Examples 3-1 to 3-3 are shown in the following table, in which the HIL was doped with 2 compounds at the weight ratios as recorded.

[0285] Table 5 Partial device structures of Examples 3-1 to 3-3 and Comparative Examples 3-1 to 3-3

[0286]

[0287]

[0288] The structures of the newly used compounds in the devices are shown below:

[0289]

[0290] The device performances of Examples 3-1 to 3-3 and Comparative Examples 3-1 to 3-3 were measured. Among them, the color coordinates (CIE), voltage and external quantum efficiency (EQE) were measured under the condition that the current density was 15 mA / cm 2 ; the η of the device was calculated according to the EQE and voltage and according to ; the device lifetime (LT95) was the measured time for the luminance to decay to 95% of the initial luminance under the driving of a constant current density of 80 mA / cm 2 . These data are shown in Table 6.

[0291] Table 6 Device data

[0292]

[0293] From the color coordinates, it can be seen that the color coordinates of the examples and comparative examples shown are consistent.

[0294] Examples 3-1 to 3-3 and Comparative Examples 3-1 to 3-3 are all fluorescent light-emitting devices, and the EQEs of the devices are all 0.25.

[0295] ​The same materials were used in the HIL of Example 3-1 as in the HIL of Comparative Example 3-1, but in the HIL of Comparative Example 3-1, the doping ratio of compound 1-2 was 3%, and the conductivity of the HIL was only 2.4*10 -5 S / m, the conductivity was too low, which led to weak hole injection ability of the HIL, causing the device voltage to rise sharply, although the EQE of Comparative Example 3-1 was as high as 9.7%, the η of the device was only 6.26, which still only showed poor overall performance of the device, and the weak hole injection ability of the HIL also had a negative impact on the instability of the device. In contrast, in the HIL of Example 3-1, the doping ratio of compound 1-2 as the first organic material was 20%, and the conductivity of the HIL was 89*10 -5 S / m, which was greater than 3*10 -5 S / m, and the use of this HIL could obtain a blue light device with excellent overall performance, with a voltage of only 4.4V at 15mA / cm 2 , an EQE of 9.0%, and an η of 8.18; and a device lifetime (LT95) of 79h at 80mA / cm 2 , which was nearly 19 times higher than the device lifetime of Comparative Example 3-1. Thus, by controlling the first organic layer conductivity to be greater than or equal to 3*10 -5 S / m, the overall performance of the device could be improved.

[0296] In the HIL of Example 3-2, the doping ratio of compound 1-2 was increased to 30%, and the conductivity of the HIL was slightly higher than when the doping ratio of compound 1-2 was 20%, so the device voltage was further reduced to 4.2V, and the device lifetime was increased to 170h, although the EQE was slightly reduced to 8.3%, the η was still 7.90, but the overall performance of this device was more excellent than the device shown in Comparative Example 3-2 (η was 7.19), which was widely used at present, and the doping material used in Comparative Example 3-2 was compound PD-1, and the LUMO and HOMO energy level difference of compound PD-1 and HTM1 was only 0.09eV, and when the doping ratio was 2%, the conductivity reached 1.1*10 -3 S / m, although the HIL achieved good hole injection ability and obtained high level of device performance, but the LUMO energy level of compound PD-1 in the HIL and the HOMO energy level of compound HT-7 were only 0.09eV, which was not conducive to further regulating the balance of carriers in the device; in contrast, Example 3-2 further improved the device performance on the basis of the high level of Comparative Example 1-2 by reasonably selecting the HIL material: the EQE was increased by 5%, the lifetime was increased by 139%, and the voltage remained the same. In summary, when the HOMO of the second organic material is ≤-5.1eV, the LUMO 第一有机材料 -HOMO第二有机材料 When the energy level difference between the LUMO of the first organic material and the HOMO of the second organic material is greater than or equal to 0.3 eV, the conductivity of the first organic layer HIL can be controlled by controlling the doping ratio of the first organic material, and a blue light device with excellent comprehensive performance can be obtained.

[0297] In the HIL of Example 3-3, the doping material is compound 3-2, the energy level difference between the LUMO of compound 3-2 and the HOMO of HT-7 is 0.33 eV, and the energy level difference is greater than 0.3 eV, so the conductivity of the HIL can be conveniently regulated by adjusting the doping ratio of compound 3-2: when the doping ratio of compound 3-2 is 10%, the conductivity of the HIL is 1.4*10 -3 S / m, and a blue light device with excellent comprehensive performance is obtained using the above HIL, and the voltage is only 4.2 V at 15 mA / cm - 5 S / m, and a blue light device with excellent comprehensive performance is obtained using the above HIL, and the voltage is only 4.2 V at 15 mA / cm 2 S / m, and a blue light device with excellent comprehensive performance is obtained using the above HIL, and the voltage is only 4.2 V at 15 mA / cm 2 The device lifetime reaches (LT95) 149 h. In Comparative Example 3-3 as a comparison, the doping ratio of compound 4-2 is 2%, and the conductivity is only 2.6*10 -5 S / m, due to the low conductivity, it is difficult for holes to be injected from the anode to the HIL, so that the device voltage is higher than that of Example 3-3 by 43%, although the low conductivity of the HIL brings a small increase in EQE, the η is only 6.27, and the difficulty in hole injection also causes the instability of the device, and the lifetime of Example 3-3 is 24.8 times longer than that of Comparative Example 3-3.

[0298] Therefore, through the comparison of Examples 3-1 to 3-3 and Comparative Examples 3-1 to 3-3, it is proved that when the HOMO of the second organic material is ≤-5.1 eV, the LUMO 第一有机材料 -HOMO 第二有机材料 ≥ 0.3 eV, the conductivity of the first organic layer HIL can be controlled by controlling the doping ratio of the first organic material, and when the conductivity of the first organic layer is greater than or equal to 3*10 -5 S / m, a blue light device with excellent comprehensive performance can be obtained.

[0299] From the above comparison and analysis of examples and comparative examples, it can be seen that the first organic material and the second organic material with specific selection are used as the first organic layer (HIL) in the present application, the conductivity of the HIL is controlled by regulating the concentration of the first organic material, so that the conductivity of the HIL is greater than or equal to 3*10 -5 S / m. The organic electroluminescent device disclosed in the present application, which comprises the first organic layer with the above characteristics, can exhibit excellent comprehensive device performance of high efficiency voltage ratio (low voltage and high efficiency) and long lifetime in devices of different light emitting colors, and has great potential for being widely used in commercial devices.

[0300] It should be understood that various embodiments described herein are merely exemplary and that the scope of the application is not intended to be limited to these embodiments. Thus, it will be apparent to those skilled in the art that modifications of the application as described herein can occur to persons of ordinary skill in the art upon reading the foregoing description. Numerous variations and modifications have been disclosed in the foregoing description, and others will also become apparent to those skilled in the art. It is the intention of the inventors to embrace all such variations and modifications as fall within the scope of the application. Accordingly, the application as set forth is not to be limited by the foregoing description, but is to be understood to include all variations and modifications falling within the scope of the application. The word "comprising" and variations such as "comprise", "comprises" and "comprised of" as used herein are to be interpreted in an inclusive sense as encompassing items in the list following the word and any additional items. The word "comprising" and variations are to be interpreted as "consisting of" when the context requires.

Claims

1. An organic electroluminescent device comprising: an anode, a cathode, and an organic layer disposed between the anode and the cathode; wherein the organic layer comprises a first organic layer, and the first organic layer comprises a first organic material and a second organic material; the LUMO energy level of the first organic material is LUMO 第一有机材料 , the HOMO energy level of the second organic material is HOMO 第二有机材料 , and the HOMO 第二有机材料 ≤ -5.1 eV, and the LUMO 第一有机材料 - HOMO 第二有机材料 ≥ 0.3 eV; The electrical conductivity of the first organic layer is ≥ 3*10 -5 S / m.

2. An organic electroluminescent device comprising: an anode, a cathode, and an organic layer disposed between the anode and the cathode; wherein the organic layer comprises a first organic layer; the first organic layer comprises a first organic material and a second organic material, and a LUMO energy level of the first organic material is LUMO 第一有机材料 , a HOMO energy level of the second organic material is HOMO 第二有机材料 , and the LUMO 第一有机材料 -HOMO 第二有机材料 ≥ 0.3 eV, an electrical conductivity of the first organic layer is ≥ 3*10 -5 S / m, and the second organic material has a structure represented by formula H: in formula H, Ar1, Ar2, and Ar3are the same or different at each occurrence selected from a substituted or unsubstituted aryl having 6-30 carbon atoms, or a substituted or unsubstituted heteroaryl having 3-30 carbon atoms; when Ar1, Ar2, and Ar3are the same or different at each occurrence selected from a substituted aryl having 6-30 carbon atoms, or a substituted heteroaryl having 3-30 carbon atoms, the aryl or heteroaryl is substituted with one or more groups selected from the group consisting of deuterium, a halogen, an unsubstituted alkyl having 1-20 carbon atoms, an unsubstituted cycloalkyl having 3-20 ring carbon atoms, an unsubstituted heteroalkyl having 1-20 carbon atoms, an unsubstituted heterocyclyl having 3-20 ring atoms, an unsubstituted aralkyl having 7-30 carbon atoms, an unsubstituted alkoxy having 1-20 carbon atoms, an unsubstituted aryloxy having 6-30 carbon atoms, an unsubstituted alkenyl having 2-20 carbon atoms, an unsubstituted alkynyl having 2-20 carbon atoms, an unsubstituted aryl having 6-30 carbon atoms, an unsubstituted heteroaryl having 3-30 carbon atoms, an unsubstituted alkylsilyl having 3-20 carbon atoms, an unsubstituted arylsilyl having 6-20 carbon atoms, an unsubstituted alkylgermanyl having 3-20 carbon atoms, an unsubstituted arylgermanyl having 6-20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a thiol group, a sulfinyl group, a sulfonyl group, a phosphine group, and combinations thereof; adjacent substituents Ar1, Ar2, and Ar3are optionally linked to form a ring.

3. The organic electroluminescent device according to claim 1 or 2, wherein LUMO 第一有机材料 -HOMO 第二有机材料 ≥ 0.33 eV.

4. The organic electroluminescent device according to claim 1 or 2, wherein LUMO 第一有机材料 -HOMO 第二有机材料 ≥ 0.4 eV.

5. The organic electroluminescent device according to claim 1 or 2, wherein LUMO 第一有机材料 -HOMO 第二有机材料 ≥ 0.45 eV.

6. The organic electroluminescent device according to claim 1 or 2, wherein the HOMO 第二有机材料 ≤ -5.13 eV.

7. The organic electroluminescent device according to claim 1 or 2, wherein HOMO 第二有机材料 ≤ -5.2 eV.

8. The organic electroluminescent device according to claim 1 or 2, wherein The electrical conductivity of the first organic layer is greater than or equal to 5*10 -5 S / m.

9. The organic electroluminescent device according to claim 1 or 2, wherein The electrical conductivity of the first organic layer is greater than or equal to 7*10 -5 S / m.

10. The organic electroluminescent device according to claim 1 or 2, wherein the first organic material comprises 0.1% to 90% by weight of the first organic layer.

11. The organic electroluminescent device according to claim 1 or 2, wherein the first organic material comprises 1% to 50% by weight of the first organic layer.

12. The organic electroluminescent device according to claim 1 or 2, wherein the first organic material comprises 2% to 30% by weight of the first organic layer.

13. The organic electroluminescent device according to claim 1 or 2, wherein the first organic layer has a thickness of 1-30 nm.

14. The organic electroluminescent device according to claim 1 or 2, wherein the first organic layer has a thickness of 5-15 nm.

15. The organic electroluminescent device according to claim 1 or 2, wherein the organic electroluminescent device further comprises a second organic layer, the second organic layer comprising a second organic material.

16. The organic electroluminescent device according to claim 1 or 2, wherein the second organic layer has a thickness of 10-200 nm.

17. The organic electroluminescent device according to claim 1 or 2, wherein the first organic layer is in direct contact with the anode.

18. A first organic electroluminescent device comprising: an anode, a cathode, and an organic layer disposed between the anode and the cathode; wherein the organic layer comprises a first organic layer, the first organic layer is in direct contact with the anode, and comprises a first organic material and a second organic material; The electrical conductivity of the first organic layer is ≥ 3*10 -5 S / m; The first organic electroluminescent device has an efficiency-voltage ratio η at an equivalent current density which is equal to or greater than 104% of η of a second organic electroluminescent device; wherein the is the proportion of excitons allowed to emit in quantum mechanics; the device structure of the second organic electroluminescent device is identical to that of the first organic electroluminescent device, except for the following differences: the organic layer in direct contact with the anode in the second organic electroluminescent device is a third organic layer and comprises a third organic material and a fourth organic material, and the materials of at least one of the two groups of materials consisting of the first organic material and the third organic material, and the second organic material and the fourth organic material, are identical. and the third organic layer in the second organic electroluminescent device at least satisfies one of the following conditions: 1) the HOMO energy level of the fourth organic material is HOMO 第四有机材料 , and HOMO 第四有机材料 -5.1 eV; 2) the LUMO energy level of the third organic material is LUMO 第三有机材料 , the HOMO energy level of the fourth organic material is HOMO 第四有机材料 , LUMO 第三有机材料 - HOMO 第四有机材料 < 0.3 eV; 3) the electrical conductivity of the third organic layer is less than 3*10 -5 S / m.

19. The first organic electroluminescent device according to claim 18, wherein In the first organic electroluminescence device, a LUMO energy level of the first organic material is LUMO 第一有机材料 , a HOMO energy level of the second organic material is HOMO 第二有机材料 , and the LUMO 第一有机材料 -HOMO 第二有机材料 ≥ 0.3 eV.

20. The first organic electroluminescent device of claim 18, wherein, In the first organic electroluminescence device, a HOMO energy level of the second organic material is HOMO 第二有机材料 , and the HOMO 第二有机材料 ≤ -5.1 eV.

21. The first organic electroluminescent device of claim 18, wherein, The EQE of the first organic electroluminescent device is more than 103% of the EQE of the second organic electroluminescent device at the same current density.

22. The first organic electroluminescent device of claim 18, wherein, The EQE of the first organic electroluminescent device is more than 110% of the EQE of the second organic electroluminescent device.

23. The first organic electroluminescent device of claim 18, wherein, The EQE of the first organic electroluminescent device is more than 120% of the EQE of the second organic electroluminescent device.

24. The first organic electroluminescent device of claim 18, wherein, The first organic electroluminescence device has η > 7.19 under the condition of 15 mA / cm 2 under the condition of 15 mA / cm2.

25. The first organic electroluminescent device of claim 18, wherein, The first organic electroluminescence device has an η > 7.3 under 15 mA / cm 2 at 20 mA / cm2.

26. The first organic electroluminescent device of claim 18, wherein, The first organic electroluminescence device has an η > 7.4 at 15 mA / cm 2 under the condition.

27. An organic electroluminescent device as claimed in claim 1, 2 or 18, wherein The first organic material has a structure represented by one of Formula 1 to Formula 3: In Formula 1, Formula 2 or Formula 3, E is on each occurrence identically or differently selected from N or CR1; X is on each occurrence identically or differently selected from the group consisting of NR’, CR”R”’, O, S or Se; Ring A is on each occurrence identically or differently a 5-membered heterocyclic ring, and the 5-membered heterocyclic ring comprises one endocyclic double bond, at least one N atom and at least one Q; Q is, on each occurrence, identically or differently selected from the group consisting of O, S, Se and NR N consisting of R is on each occurrence identically or differently a single substitution, a multiple substitution or no substitution; R, R1, R', R", R'", R N 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, hydroxyl, thiol, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclyl having 3-20 ring atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3-20 carbon atoms, substituted or unsubstituted arylgermanyl having 6-20 carbon atoms, and combinations thereof; and at least one of the substituents R, R1, R’, R” and R”’ is a group having at least one electron withdrawing group; adjacent substituents R, R’, R”, R”’ can optionally be linked to form a ring.

28. The organic electroluminescent device according to claim 27, wherein The first organic material has a structure represented by Formula 1 or Formula 3.

29. The organic electroluminescent device according to claim 27, wherein X is on each occurrence identically or differently selected from CR”R”’ or NR’, and R’, R” and R”’ are each a group having at least one electron withdrawing group.

30. The organic electroluminescent device according to claim 27, wherein R, R’, R” and R”’ are each a group having at least one electron withdrawing group.

31. The organic electroluminescent device according to claim 27, wherein X is on each occurrence identically or differently selected from the group consisting of:

32. The organic electroluminescent device according to claim 27, wherein X is selected from X-1.

33. The organic electroluminescent device according to claim 27, wherein Q is on each occurrence identically or differently selected from O or S.

34. An organic electroluminescent device as claimed in claim 27, wherein, R, R1is 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, phosphine oxide, unsubstituted alkyl having 1-20 carbon atoms, unsubstituted cycloalkyl having 3-20 ring carbon atoms, unsubstituted alkoxy having 1-20 carbon atoms, unsubstituted alkenyl having 2-20 carbon atoms, unsubstituted aryl having 6-30 carbon atoms, unsubstituted heteroaryl having 3-30 carbon atoms, and any of the following groups having 1-20 carbon atoms, cycloalkyl having 3-20 ring carbon atoms, alkoxy having 1-20 carbon atoms, alkenyl having 2-20 carbon atoms, aryl having 6-30 carbon atoms, heteroaryl having 3-30 carbon atoms, and combinations thereof, which are substituted by one or more of halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, SCN, OCN, SF5, boryl, sulfinyl, sulfonyl and phosphine oxide.

35. An organic electroluminescent device as claimed in claim 27, wherein, R, R1are the same or different at each occurrence and are 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, diphenylborinyl, oxaboraanthracenyl, and combinations thereof. R, R1are the same or different at each occurrence and are 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, diphenylborinyl, oxaboraanthracenyl, and combinations thereof.

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