Organic electroluminescent device and its use

Abstract

To disclose an organic electroluminescent element and use thereof.SOLUTION: An organic electroluminescent element according to the present invention comprises a metal complex having specific spectral characteristics. The metal complex can achieve performance that more closely approaches commercially required BT. 2020 light emission. With respect to the metal complex that does not meet requirements of D and AR, the organic electroluminescent element obtained by applying the metal complex to the organic electroluminescent element has higher element efficiency and more saturated green light emission, the organic electroluminescent element can meet needs for light emission of the BT. 2020 in a market, and when the light emission of the BT. 2020 is approached, still high element performance, in particular element efficiency, can be maintained and the maximum efficiency of the element can be approximately achieved. The organic electroluminescent element comprising the metal complex has a wide commercial application prospect and can achieve more saturated light emission.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] The present invention relates to organic electronic devices, such as organic electroluminescent devices, and in particular to organic electroluminescent devices comprising metal complexes with specific spectral properties, display assemblies comprising the organic electroluminescent devices, and the use of the metal complexes in organic photovoltaic devices. [Background technology]

[0002] Organic electronic devices include, but are not limited to, organic light-emitting diodes (OLEDs), organic field-effect transistors (O-FETs), organic light-emitting transistors (OLETs), organic photovoltaic cells (OPVs), dye-sensitized solar cells (DSSCs), organic photodetectors, organic photosensitive devices, organic field-effect devices (OFQDs), light-emitting electrochemical cells (LECs), organic laser diodes, and organic plasma light-emitting devices.

[0003] In 1987, Tang and Van Slyke of Eastman Kodak reported a bilayer organic electroluminescent device containing an arylamine hole-transporting layer and a tris-8-hydroxyquinoline-aluminum layer as the electron-transporting and emissive layers (Applied Physics Letters, 1987, 51(12):913-915). Once a bias was applied to the device, green light was emitted from the device. This invention laid the foundation for the development of modern organic light-emitting diodes (OLEDs). The most advanced OLEDs may contain multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more emissive layers between the cathode and anode. Because OLEDs are self-emissive solid-state devices, they offer tremendous potential for display and lighting applications. Furthermore, the inherent properties of organic materials, such as their flexibility, make them highly suitable for specialized applications, such as fabrication on flexible substrates.

[0004] OLEDs are divided into three different types depending on their emission mechanism. The OLED invented by Tang and van Slyke is a fluorescent OLED, which uses only singlet emission. Triplets generated in the device are wasted through nonradiative decay pathways, resulting in an internal quantum efficiency (IQE) of only 25%, hindering the commercialization of OLEDs. In 1997, Forrest and Thompson reported on phosphorescent OLEDs, which use triplet emission from heavy metal-containing complexes as the emitter. Therefore, singlet and triplet emissions can be harvested, achieving an IQE of 100%. Due to their 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 a small singlet-triplet gap, allowing excitons to transition from triplet to singlet. In TADF devices, the high IQE is due to the generation of singlet excitons by triplet excitons threading between reverse systems (reverse intersystem crossing).

[0005] OLEDs can be further divided into small molecule and polymer OLEDs depending on the form of the material used. Small molecules refer to non-polymeric organic or organometallic materials, and as long as they have a precise structure, the molecular weight of the small molecule can be large. Dendrimers, which have a well-defined structure, are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with side-chain emissive groups. Post-polymerization during the manufacturing process can turn small molecule OLEDs into polymer OLEDs.

[0006] Various methods for manufacturing OLEDs are known. Small molecule OLEDs are generally manufactured by vacuum thermal evaporation. Polymer OLEDs are manufactured by solution processes, such as spin coating, inkjet printing, and nozzle printing. Small molecule OLEDs can also be manufactured by solution processes if the material can be dissolved or dispersed in a solvent.

[0007] The emission color of an OLED can be achieved by the structural design of the emissive material. An OLED may contain one or more emissive layers to achieve a desired spectrum. While phosphorescent materials have already been successfully commercialized in green, yellow, and red OLEDs, blue phosphorescent devices still suffer from problems such as unsaturated blue, short service life, and high operating voltage. Commercially available full-color OLED displays generally use a mixed strategy, employing blue fluorescence and yellow, red, or green phosphorescence. Currently, phosphorescent OLEDs suffer from a rapid decrease in efficiency at high brightness. Furthermore, there is a demand for more saturated emission spectra, higher efficiency, and longer device service life.

[0008] Full-color displays are now widely used in our work and daily lives, such as mobile phone displays, computer monitors, and shopping mall advertising displays. They are primarily used to display information such as text, graphics, animations, videos, and recordings. In assessing the quality of a full-color display, color reproducibility is one of the most important considerations, in addition to flatness, brightness, viewing angle, and white balance. Color reproducibility generally refers to the colors that can be displayed by the RGB subpixels of a display. BT.2020 is currently the highest color gamut requirement. The higher the BT.2020 coverage of a full-color display, the better its color reproducibility. In 2012, the International Telecommunication Union (ITU) proclaimed the new UHDTV color gamut standard, Broadcast Service Television 2020 (BT.2020). However, although BT.2020 has a higher color gamut specification, the coloring of the three primary colors of BT.2020 is too saturated, making it difficult for ordinary devices to achieve.

[0009] BT.2020 requires the color coordinates of the red, green, and blue primary colors to be (0.708, 0.292), (0.131, 0.046), and (0.170, 0.797), respectively. While the red and blue light elements in currently commonly used OLED display panels can nearly meet the color gamut requirements, the performance of the green light element is limited primarily by its inability to meet the color gamut requirements. To achieve full BT.2020 coverage, the color coordinates of the green light element must be adjusted to approach the BT.2020 requirements. While single-color laser light sources can be used to achieve the BT.2020 color gamut requirements, they are currently only used in projection television displays. Furthermore, due to their relatively large physical size and high manufacturing costs, they are rarely used in high-resolution, small- to medium-sized active-matrix displays. Another potential candidate for achieving the BT.2020 color gamut requirements is quantum dots (QDs). Quantum dots have been widely studied due to their relatively narrow emission spectrum. However, quantum dot light-emitting diodes (QDs) using QDs as self-emitting elements still have stability issues and have not yet been commercialized. Micro LED technology, which involves peeling LED chips fabricated on semiconductor epitaxial wafers and transferring them to a display back panel, then electrically bonding them to the back panel circuitry, has become a hot research topic for new display technologies. Similar to LEDs, they have narrow spectrums and high color saturation, and the desired emission spectrum can be achieved by selecting appropriate semiconductor materials. However, as micro LED chips become smaller, their efficiency can also decrease. In addition to the immaturity of mass transfer technology, their application as display components for mobile devices such as cell phones has not yet been commercialized.

[0010] Organic light-emitting diode (OLED) displays are widely used in displays of various sizes, including mobile phones, tablets, laptops, and AR and VR glasses. Some studies suggest that OLEDs can consume 37% less power than LED-backlit LCDs. Therefore, OLED technology is another potential candidate for achieving the BT.2020 color gamut requirements. However, current OLED devices struggle to achieve the ideal BT.2020 color gamut coverage, and OLED products from various display and device manufacturers typically achieve less than 80% BT.2020 coverage. Therefore, how to improve the display color of OLED devices or OLED display products to meet the BT.2020 requirements has become an urgent technical issue in the industry. [Prior art documents] [Non-patent literature]

[0011] [Non-Patent Document 1] Applied Physics Letters, 1987, 51(12):913~915 Summary of the Invention [Problem to be solved by the invention]

[0012] The present invention aims to provide an organic electroluminescent device that solves at least some of the above-mentioned problems. The organic electroluminescent device includes a metal complex with specific spectral characteristics. The metal complex can achieve performance that more closely matches the commercially desired BT.2020 emission, while maintaining high device performance, particularly device efficiency, even when approaching BT.2020 emission, and can generally achieve maximum device efficiency. Organic electroluminescent devices containing the metal complex have broad commercial application prospects and can achieve more saturated emission. [Means for solving the problem]

[0013] According to one embodiment of the present invention, there is provided an organic electroluminescent device including a cathode, an anode, and an organic layer disposed between the cathode and the anode, The organic layer comprises a metal M and at least one C^N bidentate ligand L coordinated to the metal M. a and a metal complex comprising the metal M is selected from metals with a relative atomic mass greater than 40; The area ratio of the photoluminescence spectrum of the metal complex at room temperature is AR, and AR≦0.331; When the metal complex has a maximum current efficiency in a top-emitting device, the corresponding color coordinates are CIE(x,y), The distance between the CIE (x, y) and the color coordinates CIE (0.170, 0.797) is D, However, an organic electroluminescence device is disclosed in which CIEy≧0.797 or D≦0.0320.

[0014] According to another embodiment of the present invention, there is further disclosed a display assembly including the organic electroluminescent device described in the above embodiment.

[0015] The organic electroluminescent device according to the present invention uses a metal complex with specific spectral characteristics (i.e., meeting D and AR requirements). Because the metal complex can achieve performance that more closely matches the commercially required BT.2020 emission, compared to metal complexes that do not meet D and AR requirements, the resulting organic electroluminescent device has higher device efficiency and more saturated green emission, satisfying the market demand for BT.2020 emission. Even when approaching BT.2020 emission, high device performance, particularly device efficiency, can still be maintained, achieving roughly maximum device efficiency. Organic electroluminescent devices containing the metal complex have broad commercial application prospects and can achieve more saturated emission. [Brief explanation of the drawings]

[0016] [Figure 1] 1 is a schematic diagram of an organic electroluminescence element according to the present invention. [Figure 2] FIG. 2 is a schematic diagram of another organic electroluminescence element according to the present invention. [Figure 3] 1 is a schematic diagram of the structure of a typical top-emission OLED device. [Figure 4] FIG. 2 is a structural schematic diagram of an element used in the simulation. [Figure 5] FIG. 1 is a schematic diagram for calculating an emission spectrum area ratio. DETAILED DESCRIPTION OF THE INVENTION

[0017] OLEDs can be fabricated on a variety of substrates, including glass, plastic, and metal. FIG. 1 illustrates, by way of example and not limitation, an organic light-emitting device 100. The drawings are not necessarily drawn to scale, and some layer structures may be omitted from the drawings, if necessary. Device 100 may include a substrate 101, an anode 110, a hole-injection layer 120, a hole-transport layer 130, an electron-blocking layer 140, an emissive layer 150, a hole-blocking layer 160, an electron-transport layer 170, an electron-injection layer 180, and a cathode 190. Device 100 may be fabricated by depositing the layers described, in order. The properties, functions, and exemplary materials of each layer are described in more detail in columns 6-10 of U.S. Pat. No. 7,279,704 B2, the entire contents of which are incorporated herein by reference.

[0018] There are many examples of each of these layers. Illustratively, U.S. Patent No. 5,844,363, incorporated herein by reference in its entirety, discloses a flexible and transparent substrate-anode combination. For example, U.S. Patent Application Publication No. 2003 / 0230980, incorporated herein by reference in its entirety, discloses that an example of a p-type doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1. Examples of host materials are disclosed in U.S. Patent No. 6,303,238 to Thompson et al., incorporated herein by reference in its entirety. For example, U.S. Patent Application Publication No. 2003 / 0230980, incorporated herein by reference in its entirety, discloses that an example of an n-type doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1. U.S. Patent Nos. 5,703,436 and 5,707,745, incorporated herein by reference in their entireties, disclose examples of cathodes, including composite cathodes having a thin metal layer, such as Mg:Ag, coated thereon with a sputter-deposited transparent conductive ITO layer. U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, incorporated herein by reference in their entireties, describe the principles and use of blocking layers in more detail. U.S. Patent Application Publication No. 2004 / 0174116, incorporated herein by reference in its entirety, provides examples of injection layers. U.S. Patent Application Publication No. 2004 / 0174116, incorporated herein by reference in its entirety, describes protective layers.

[0019] The above-described split-layer structures are provided by way of non-limiting examples. OLED functions can be achieved by combining the various layers described above, or some layers can be omitted entirely. It may also include other layers not explicitly described. Within each layer, a single material or a mixture of multiple materials can be used to achieve optimal performance. Any functional layer may also include multiple sublayers; for example, an emissive layer may have two layers of different emissive materials to achieve a desired emission spectrum.

[0020] In one embodiment, an OLED may be described as having an "organic layer" disposed between a cathode and an anode. The organic layer may include one or more layers.

[0021] An OLED also requires an encapsulation layer. As shown in FIG. 2, an organic light-emitting device 200 is shown by way of example and not limitation. The difference from FIG. 1 is that an encapsulation layer 102 may be included on the cathode 190 to protect against harmful substances, such as moisture and oxygen, from the outside. Any material capable of providing an encapsulation function, such as glass or an organic-inorganic hybrid layer, may be used as the encapsulation layer. The encapsulation layer should be disposed directly or indirectly on the exterior of the OLED device. Multilayer thin-film encapsulation is described in U.S. Pat. No. 7,968,146 B2, the entire contents of which are incorporated herein by reference.

[0022] Devices manufactured according to embodiments of the present invention may be incorporated into a variety of consumer products having one or more electronic modules (or units) of the device, including, for example, flat panel displays, monitors, medical monitors, televisions, billboards, indoor or outdoor lighting and / or signal lamps, head-up displays, fully or partially transparent displays, flexible displays, smartphones, flat panel computers, flat panel mobile phones, wearable devices, smart watches, laptop computers, digital cameras, portable video cameras, viewfinders, microdisplays, 3-D displays, automotive displays, and tail lights.

[0023] The materials and structures described herein may also be used in the other organic electronic devices listed above.

[0024] "Top" means furthest from the substrate, and "bottom" means closest to the substrate. When a first layer is described as being "on" a second layer, the first layer is relatively far from the substrate. Other layers may exist between the first and second layers, unless the first layer is specified as being "in contact with" the second layer. Illustratively, even if various organic layers exist between the cathode and anode, the cathode can still be described as being "on" the anode.

[0025] "Solution processable" means capable of being dissolved, dispersed or transported in and / or deposited from a liquid medium in the form of a solution or suspension.

[0026] It is believed that if a ligand directly enhances the photosensitizing properties of the emitting material, it may be referred to as "photosensitizing." If a ligand does not enhance the photosensitizing properties of the emitting material, it may be referred to as "auxiliary." However, it is believed that the auxiliary ligand can modify the properties of the photosensitizing ligand.

[0027] It is believed that the internal quantum efficiency (IQE) of fluorescent OLEDs may exceed the 25% spin-statistics limit due to the presence of delayed fluorescence. Delayed fluorescence may be generally divided into two types: P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).

[0028] On the other hand, E-type delayed fluorescence relies on the conversion of triplet and singlet excited states rather than the collision of two triplets. Compounds capable of generating E-type delayed fluorescence must have an extremely small singlet-triplet gap to allow for the energy state conversion. Thermal energy can activate the triplet-to-singlet transition. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). A notable feature of TADF is that the delayed component increases with increasing temperature. If the rate of threading between reverse intersystems (RISC) is sufficiently fast, the non-radiative decay from the triplet can be minimized, and the proportion of backfilled singlet excited states can reach 75%. The total proportion of singlets can be 100%, far exceeding the 25% spin statistics of the exciton due to electrochemical reactions.

[0029] The characteristics of E-type delayed fluorescence can be seen from an excited complex system or a single compound. Without being limited by theory, E-type delayed fluorescence is observed when the emissive material has a small singlet-triplet energy gap (ΔE S-T ) is required. Organic non-metal-containing donor-acceptor emissive materials have the potential to achieve this. The emission of these materials is typically characterized as donor-acceptor charge transition (CT) emission. In these donor-acceptor compounds, the spatial separation between the HOMO and LUMO is generally small, ΔE S-T These states may include CT states. Donor-acceptor emissive materials are typically constructed by combining an electron donor moiety (e.g., an amine group or a carbazole derivative) with an electron acceptor moiety (e.g., an N-containing six-membered aromatic ring).

[0030] As used herein, the term "color coordinates" refers to the corresponding coordinates in the CIE 1931 color space.

[0031] The structure of a typical top-emission OLED device is shown in Figure 3. OLED device 300 includes an anode 110, a hole-injection layer (HIL) 120, a hole-transport layer (HTL) 130, an electron-blocking layer (EBL) 140 (also called a prime layer), an emissive layer (EML) 150, a hole-blocking layer (HBL) 160 (the hole-blocking layer 160 is an optional layer), an electron-transport layer (ETL) 170, an electron-injection layer (EIL) 180, a cathode 190, a capping layer 191, and an encapsulation layer 102. The anode 110 is made of a material or a combination of materials with high reflectivity, including, but not limited to, Ag, Al, Ti, Cr, Pt, Ni, TiN, and combinations of the above materials with ITO and / or MoOx (molybdenum oxide). Typically, the reflectivity of the anode is greater than 50%, preferably greater than 70%, and more preferably greater than 80%. The cathode 190 is a semi-transparent or transparent conductive material, including, but not limited to, MgAg alloy, MoOx, Yb, Ca, ITO, IZO, or a combination thereof, and has an average transmittance of greater than 15% for light in the visible light range, preferably greater than 20%, and more preferably greater than 25% for light in the visible light range. The hole injection layer 120 may be a single-material layer, such as the commonly used HATCN. The hole injection layer 120 may further be a hole transport material doped with a certain percentage of a p-type conductive dopant; the doping ratio is usually no more than 5%, and commonly between 1% and 3%. The electron blocking layer (EBL) 140 is an optional layer, but because it closely matches the energy level of the host material, a device structure that includes an EBL is typically used. The thickness of the hole transport layer is typically 100 nm to 200 nm, and because a microcavity effect exists in top-emission devices, the thickness of the hole transport layer or electron blocking layer can be adjusted to tune the microcavity of the device.For example, to optimize the microcavity effect of a top-emitting OLED device, i.e., to maximize the current efficiency, the microcavity can be adjusted by adjusting the thickness of the HTL after keeping the thickness of the EBL constant. Those skilled in the art should understand that the difference between two top-emitting devices is only the material used in one of the organic layers. For example, if a different organic material is used only in the EML (while other functional layers are similar), the refractive indexes of the different organic materials in the EML may be slightly different, so the optimal microcavity lengths of the two top-emitting devices may be slightly different. That is, to achieve the same setting conditions (e.g., CEmax, CIEx coordinate, or EQEmax) for different top-emitting devices, the optimal microcavity lengths may be slightly different.

[0032] As used herein, the term "simulation" refers to optical simulation software based solely on the refractive index curves and thicknesses of the materials in each layer, and does not include electrical simulation. The simulation software used in this invention is Setfos 5.0, a semiconductor thin film optical simulation software developed by FLUXiM. The device structure used in the simulation is device 400 shown in FIG. 4. Specifically, on a 0.7 mm thick glass substrate, the first electrode (i.e., anode) uses a three-layer structure of ITO (75 Å) / Ag (1500 Å) / ITO (150 Å). The HIL (hole injection layer) is composed of compound HT and compound PD (weight ratio 97:3) and has a thickness of 100 Å. The HTL (hole transport layer) is composed of compound HT. The HTL is a microcavity-controlling layer, and its thickness is optimized to adjust the microcavity within the range of 1000-1500 Å, meeting the requirements of top-emitting devices. On the HTL, an EBL (electron blocking layer) is formed with compound PH-23 and has a thickness of 50 Å. On the EBL, an EML is formed with compound PH-1, compound H-40, and an organic light-emitting dopant (the weight ratio of the light-emitting layer, compound PH-1, compound H-40, and organic light-emitting dopant is 48:48:4) and has a thickness of 400 Å. On the EML, a HBL (hole blocking layer) is formed with compound H-2 and has a thickness of 50 Å. On the HBL, an ETL (electron transport layer) is formed with compound ET and compound Liq (weight ratio of 40:60) and has a thickness of 350 Å. On the ETL, the second electrode (i.e., cathode) is formed of an alloy of Mg and Ag (weight ratio 9:1) and has a thickness of 230 Å. An 800 Å thick CPL (capping layer) is placed on the cathode. Glass is used as an encapsulation layer on the CPL. The specific structure of the above compound is shown in the device example below. Since Setfos 5.0 is optical simulation software, it is only necessary to determine the thickness and refractive index of each layer in the device structure during simulation (the refractive index used for each organic layer is the refractive index corresponding to a material thickness of 300 Å).Therefore, the materials of each layer are not limiting but merely illustrative. By inputting PL spectrum data of the organic light-emitting dopant used in the EML into the simulation software, it is possible to simulate the performance changes that organic light-emitting dopant materials with different PL spectra can bring to the device. In addition, the composite position in the EML is set as an intermediate position in the light-emitting layer in the software.

[0033] As used herein, the method for measuring the refractive index of an organic material is to deposit a 30 nm thick layer of material on a silicon wafer in an Angstrom Engineering deposition machine, and then measure it using an ellipsometer manufactured by Beijing Liangtong Science and Technology Co., Ltd. to obtain a refractive index curve for wavelengths from 400 nm to 800 nm.

[0034] As used herein, the PL spectrum of the organic light-emitting doped material is measured using a fluorescence spectrophotometer, model number: Liang Optoelectronics F98, manufactured by Shanghai Liang Optoelectronics Co., Ltd., to measure the photoluminescence spectrum (PL) and half-width data of the material to be measured. Specifically, the material sample to be measured is dissolved in HPLC-grade toluene at a concentration of 1 x 10 -6 A mol / L solution is prepared, and nitrogen gas is introduced into the prepared solution to remove oxygen for 5 minutes. The solution is then excited with light of 500 nm wavelength at room temperature (298 K), and the emission spectrum is measured, and the half-width data is read directly from the spectrum.

[0035] Definitions of Substituent Terminology

[0036] Halogen or halide, as used herein, includes fluorine, chlorine, bromine and iodine.

[0037] As used herein, alkyl groups include straight-chain and branched-chain alkyl groups. The alkyl groups may be alkyl groups having 1 to 20 carbon atoms, preferably alkyl groups having 1 to 12 carbon atoms, and more preferably alkyl groups having 1 to 6 carbon atoms. Illustrative examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-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, and 3-methylpentyl. Among these, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl and n-hexane are preferred. The alkyl group may be substituted.

[0038] As used herein, the term "cycloalkyl group" includes cyclic alkyl groups. The cycloalkyl group may be a cycloalkyl group having 3 to 20 ring carbon atoms, and is preferably a cycloalkyl group 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, and 2-norbornyl. Of these, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, and 4,4-dimethylcyclohexyl are preferred. The cycloalkyl group may be substituted.

[0039] As used herein, a heteroalkyl group refers to an alkyl group in which one or more carbon atoms in the alkyl chain are substituted with a heteroatom selected from the group consisting of nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium, and boron. The heteroalkyl group may be a heteroalkyl group having 1 to 20 carbon atoms, preferably a heteroalkyl group having 1 to 10 carbon atoms, and more preferably a heteroalkyl group having 1 to 6 carbon atoms. Illustrative examples of heteroalkyl groups include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermaniummethyl, trimethylgermaniumethyl, trimethylgermaniumisopropyl, dimethylethylgermaniummethyl, dimethylisopropylgermaniummethyl, tert-butyldimethylgermaniummethyl, triethylgermaniummethyl, triethylgermaniumethyl, triisopropylgermaniummethyl, triisopropylgermaniumethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, trimethylsilylisopropyl, triisopropylsilylmethyl, and triisopropyloylsilylethyl. Heteroalkyl groups may also be substituted.

[0040] As used herein, the term "alkenyl group" includes linear, branched, and cyclic olefin groups. The linear alkenyl group may be an alkenyl group having 2 to 20 carbon atoms, and preferably an alkenyl group having 2 to 10 carbon atoms. Examples of alkenyl groups include vinyl, propylene, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cycloheptatrienyl, cyclooctenyl, cyclooctatetraenyl, and norbornylalkenyl groups. The alkenyl groups may be substituted.

[0041] As used herein, the term "alkynyl group" includes straight-chain alkynyl groups. The alkynyl group may be an alkynyl group having 2 to 20 carbon atoms, preferably an alkynyl group having 2 to 10 carbon atoms. Examples of alkynyl groups include ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3,3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3,3-diisopropyl-1-pentynyl, phenylethynyl, and phenylpropynyl groups. Of these, ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, and phenylethynyl are preferred. The alkynyl group may be substituted.

[0042] As used herein, the term "aryl group" or "aromatic group" refers to both non-fused and fused systems. The aryl group may be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene, with phenyl, biphenyl, terphenyl, triphenylene, fluorene, and naphthalene being preferred. 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-tribiphenyl-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-dimethylphenyl, mesitylene, and m-tetraphenyl. The aryl group may also be substituted.

[0043] As used herein, the term "heterocyclic group" refers to a non-aromatic cyclic group. Non-aromatic heterocyclic groups include saturated heterocyclic groups having 3 to 20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3 to 20 ring atoms, at least one ring atom of which is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron atoms. Non-aromatic heterocyclic groups preferably have 3 to 7 ring atoms and contain at least one heteroatom such as nitrogen, oxygen, silicon, or sulfur. Examples of non-aromatic heterocyclic groups include oxiranyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxopentyl, dioxanyl, aziridinyl, dihydropyrrole, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxacycloheptatrienyl, thiacycloheptatrienyl, azacycloheptatrienyl, and tetrahydrosilole. Heterocyclic groups may also be substituted.

[0044] As used herein, the term "heteroaryl group" refers to both non-fused and fused heteroaromatic groups containing 1 to 5 heteroatoms, at least one of which is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron. The term "isoaryl group" also refers to heteroaryl groups. The heteroaryl group may be a heteroaryl group containing 3 to 30 carbon atoms, preferably a heteroaryl group containing 3 to 20 carbon atoms, and more preferably a heteroaryl group containing 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridoindole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indenoazine, benzoxazole, benzisoxazole, Heteroaryl groups include benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzofuranpyridine, furandipyridine, benzothienopyridine, thienobipyridine, benzoselenopyridine, and selenobenzopyridine, and preferably include dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborane, 1,3-azaborane, 1,4-azaborane, borazole, and their aza analogs. Heteroaryl groups may also be substituted.

[0045] As used herein, the alkoxy group refers to an -O-alkyl group, an -O-cycloalkyl group, an -O-heteroalkyl group, or an -O-heterocyclic group. Examples and preferred examples of the alkyl group, the cycloalkyl group, the heteroalkyl group, and the heterocyclic group are the same as those described above. The alkoxy group may be an alkoxy group having 1 to 20 carbon atoms, and is preferably an alkoxy group having 1 to 6 carbon atoms. Examples of the alkoxy group include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy, and ethoxymethyloxy. The alkoxy group may be substituted.

[0046] As used herein, the aryloxy group is represented by an -O-aryl group or an -O-heteroaryl group. Examples and preferred examples of the aryl group and heteroaryl group are the same as those described above. The aryloxy group may be an aryloxy group having 6 to 30 carbon atoms, and preferably an aryloxy group having 6 to 20 carbon atoms. Examples of the aryloxy group include phenoxy and biphenoxy. The aryloxy group may be substituted.

[0047] As used herein, the term "aralkyl group" includes an alkyl group substituted with an aryl group. The aralkyl group may be an aralkyl group having 7 to 30 carbon atoms, preferably an aralkyl group having 7 to 20 carbon atoms, and more preferably an aralkyl group having 7 to 13 carbon atoms. Examples of the aralkyl group include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl-tert-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthyl-ethyl, 2-β-naphthyl-ethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, p-methylbenzyl, m-methylbenzyl, o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl, o ... Aralkyl groups include 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. Among these, benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, and 2-phenylisopropyl are preferred. The aralkyl group may also be substituted.

[0048] As used herein, the term "alkylsilyl group" includes silyl groups substituted with an alkyl group. The alkylsilyl group may be an alkylsilyl group having 3 to 20 carbon atoms, and is preferably an alkylsilyl group having 3 to 10 carbon atoms. Examples of alkylsilyl groups include trimethylsilyl, triethylsilyl, methyldiethylsilyl, ethyldimethylsilyl, tripropylsilyl, tributylsilyl, triisopropylsilyl, methyldiisopropylsilyl, dimethylisopropylsilyl, tri-tert-butylsilyl, triisobutylsilyl, dimethyl-tert-butylsilyl, and methyldi-tert-butylsilyl. The alkylsilyl group may also be substituted.

[0049] As used herein, the term "arylsilyl group" refers to a silyl group substituted with at least one aryl group. The arylsilyl group may be an arylsilyl group having 6 to 30 carbon atoms, and is preferably an arylsilyl group having 8 to 20 carbon atoms. Examples of the arylsilyl group include triphenylsilyl, phenyl dibiphenylsilyl, diphenyl biphenylsilyl, phenyl diethylsilyl, diphenyl ethylsilyl, phenyl dimethylsilyl, diphenyl methylsilyl, phenyl diisopropylsilyl, diphenyl isopropylsilyl, diphenyl butylsilyl, diphenyl isobutylsilyl, and diphenyl-tert-butylsilyl. The arylsilyl group may be substituted.

[0050] As used herein, the term "alkylgermanium group" includes a germanium group substituted with an alkyl group. The alkylgermanium group may be an alkylgermanium group having 3 to 20 carbon atoms, and is preferably an alkylgermanium group having 3 to 10 carbon atoms. Examples of the alkylgermanium group include a trimethylgermanium group, a triethylgermanium group, a methyldiethylgermanium group, an ethyldimethylgermanium group, a tripropylgermanium group, a tributylgermanium group, a triisopropylgermanium group, a methyldiisopropylgermanium group, a dimethylisopropylgermanium group, a tri-tert-butylgermanium group, a triisobutylgermanium group, a dimethyl-tert-butylgermanium group, and a methyldi-tert-butylgermanium group. The alkylgermanium group may also be substituted.

[0051] As used herein, the term "arylgermanium group" refers to a germanium group substituted with at least one aryl or heteroaryl group. The arylgermanium group may be an arylgermanium group having 6 to 30 carbon atoms, and preferably an arylgermanium group having 8 to 20 carbon atoms. Examples of the arylgermanium group include a triphenylgermanium group, a phenyldibiphenylgermanium group, a diphenylbiphenylgermanium group, a phenyldiethylgermanium group, a diphenylethylgermanium group, a phenyldimethylgermanium group, a diphenylmethylgermanium group, a phenyldiisopropylgermanium group, a diphenylisopropylgermanium group, a diphenylbutylgermanium group, a diphenylisobutylgermanium group, and a diphenyl-tert-butylgermanium group. The arylgermanium group may also be substituted.

[0052] The "aza" in azadibenzofuran, azadibenzothiophene, etc., refers to the replacement of one or more C—H groups in the corresponding aromatic fragment with a nitrogen atom. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline, and other analogs having two or more nitrogens in the ring system. Those skilled in the art can easily imagine other nitrogen analogs of the above-mentioned aza derivatives, and all of these analogs are defined as being included in the terminology described herein.

[0053] In the present invention, unless otherwise specified, the following groups are included: a substituted alkyl group, a substituted cycloalkyl group, a substituted heteroalkyl group, a substituted heterocyclic group, a substituted aralkyl group, a substituted alkoxy group, a substituted aryloxy group, a substituted alkenyl group, a substituted alkynyl group, a substituted aryl group, a substituted heteroaryl group, a substituted alkylsilyl group, a substituted arylsilyl group, a substituted alkylgermanium group, a substituted arylgermanium group, a substituted amino group, a substituted acyl group, a substituted carbonyl group, a substituted carboxyl group, a substituted ester group, a substituted sulfonyl group, a substituted hydroxyl group, a ... When any of the terms from the group consisting of alkyl, cycloalkyl, heteroalkyl, heterocyclyl, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermanium, arylgermanium, amino, acyl, carbonyl, carboxyl, ester, sulfinyl, sulfonyl, and phosphino groups is used, it means that any one of alkyl, cycloalkyl, heteroalkyl, heterocyclyl, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermanium, arylgermanium, amino, acyl, carbonyl, carboxyl, ester, sulfinyl, sulfonyl, and phosphino groups is used. The group is selected from the group consisting of deuterium, halogen, an unsubstituted alkyl group having 1 to 20 carbon atoms, an unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, an unsubstituted heteroalkyl group having 1 to 20 carbon atoms, an unsubstituted heterocyclic group having 3 to 20 ring atoms, an unsubstituted aralkyl group having 7 to 30 carbon atoms, an unsubstituted alkoxy group having 1 to 20 carbon atoms, an unsubstituted aryloxy group having 6 to 30 carbon atoms, an unsubstituted alkenyl group having 2 to 20 carbon atoms, an unsubstituted alkynyl group having 2 to 20 carbon atoms, an unsubstituted aryl group having 6 to 30 carbon atoms, an unsubstituted heteroxy group having 3 to 30 carbon atoms, an unsubstituted aryl ... This means that the aryl group may be substituted with one or more groups selected from the group consisting of an unsubstituted alkylsilyl group having 3 to 20 carbon atoms, an unsubstituted arylsilyl group having 6 to 20 carbon atoms, an unsubstituted alkylgermanium group having 3 to 20 carbon atoms, an unsubstituted arylgermanium group having 6 to 20 carbon atoms, an unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

[0054] When describing a molecular fragment as being attached to another moiety by a substituent or otherwise, it should be understood that the designation can be defined as either the fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or the entire molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, the designations of the substituents or different modes of attachment of the fragment are considered equivalent.

[0055] In the compounds described herein, hydrogen atoms may be partially or completely replaced with deuterium.Other atoms, such as carbon and nitrogen, may also be replaced with other stable isotopes thereof.In order to improve the efficiency and stability of the device, it may be preferable to replace other stable isotopes in the compound.

[0056] In the compounds referred to herein, multiple substitution refers to a range up to the most available substitution, including double substitution. When a substituent in a compound referred to herein is referred to as multiple substitution (including double substitution, triple substitution, quadruple substitution, etc.), it means that the substituent may be present at multiple available substitution positions on the bond structure, and the substituents present at all available substitution positions may be the same structure or different structures.

[0057] Unless specifically limited, adjacent substituents in the compounds mentioned herein may be bonded to form a ring, and adjacent substituents in the compounds may not be bonded to form a ring. In the compounds mentioned herein, adjacent substituents may be bonded to form a ring, including not only the situation where adjacent substituents may be bonded to form a ring, but also the situation where adjacent substituents are not bonded to form a ring. When adjacent substituents may be bonded to form a ring, the ring formed may be monocyclic or polycyclic, and may be an alicyclic, heteroalicyclic, aryl, or heteroaryl ring. In such descriptions, adjacent substituents may refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to carbon atoms further apart. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.

[0058] The statement that adjacent substituents may be bonded to form a ring is also understood to mean that two substituents bonded to the same carbon atom are bonded to each other by a chemical bond to form a ring, which can be exemplified by the following formula: [ka]

[0059] The statement that adjacent substituents may be bonded to form a ring is also understood to mean that two substituents bonded to carbon atoms that are directly bonded to each other are bonded to each other by a chemical bond to form a ring, which can be exemplified by the following formula: [ka]

[0060] The statement that adjacent substituents may be bonded to form a ring is also recognized as meaning that two substituents bonded to carbon atoms further apart are bonded to each other by a chemical bond to form a ring, which can be exemplified by the following formula: [ka]

[0061] According to one embodiment of the present invention, there is provided an organic electroluminescent device including a cathode, an anode, and an organic layer disposed between the cathode and the anode, The organic layer comprises a metal M and at least one C^N bidentate ligand L coordinated with the metal M. a and a metal complex comprising the metal M is selected from metals with a relative atomic mass greater than 40; The area ratio of the photoluminescence spectrum of the metal complex at room temperature is AR, and AR≦0.331; When the metal complex has a maximum current efficiency in a top-emitting device, the corresponding color coordinates are CIE(x,y), The distance between the CIE (x, y) and the color coordinates CIE (0.170, 0.797) is D, However, an organic electroluminescence device is disclosed in which CIEy≧0.797 or D≦0.0320.

[0062] In this specification, the distance between the CIE (x, y) and the color coordinates CIE (0.170, 0.797) is D, and the calculation formula for D is

number

[0063] As used herein, "top-emission element" in the phrase "when the metal complex has the maximum current efficiency in a top-emission element, the corresponding color coordinates are CIE (x, y)" refers to any element that emits light away from the substrate. Examples of top-emission elements used in this application include, but are not limited to: ITO 75 Å / Ag 1500 Å / ITO 150 Å are sequentially deposited to form an anode; Compound HT and Compound PD are deposited to form a HIL (weight ratio 97:3) with a thickness of 100 Å; Compound HT is deposited to form a HTL, controlling the microcavities within the range of 1000-1500 Å; Compound PH-23 is deposited to form an EBL; and a metal complex, Compound PH-1, and Compound H-40 are deposited to form an EML (weight ratio of Compound PH-1, Compound H-40, and metal complex 48:48:4) with a thickness of 400 Å. Compound H-2 was deposited as an HBL with a thickness of 50 Å. Compounds ET and Liq were deposited as an ETL with a weight ratio of 40:60 with a thickness of 350 Å. Metal Yb was deposited as an EIL with a thickness of 10 Å. Metal Ag and metal Mg were deposited as a cathode with a weight ratio of 9:1 with a thickness of 140 Å. Compound CP was deposited as a capping layer with a thickness of 800 Å. Specific structures of the above compounds are shown in the device examples below. The specific top-emitting device described above is merely illustrative. Those skilled in the art can adjust the top-emitting device as needed by adjusting the thickness of any layer, using appropriate material combinations and combinations for any layer, and even increasing or decreasing some functional layers. When measured in a top-emission element, if CIEy≧0.797 or D≦0.0320 is obtained and the area ratio of the photoluminescence spectrum of the metal complex contained in the top-emission element at room temperature is AR≦0.331, the metal complex belongs to the metal complex described in the present application. The application of the metal complex to any element is not limited in the present application, and the application of the metal complex to specific top-emission elements and bottom-emission elements is exemplarily shown in the examples section.Those skilled in the art can adjust the elements shown in this application or apply them to other elements, such as stacked elements, according to their understanding of the elements.

[0064] The complete structure of a top-emission device is substrate / anode / hole transport region / emissive layer / electron transport region / cathode / capping layer / encapsulation layer. The hole transport region may include a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL). The electron transport region may include a hole blocking layer (HBL), an electron transport layer (ETL), and an electron injection layer (EIL). The HBL and / or EBL may be optional depending on the device structure, and the above-mentioned functional layers may also include one or more layers depending on the device structure. The device structure of a top-emission device differs from that of a bottom-emission device due to the different light emission directions of bottom-emission and top-emission devices, which necessitates different electrode requirements. Because top-emission light is emitted from the cathode, the cathode must have high light transmittance, while the anode is typically made of a material or combination of materials with high reflectivity. For a detailed explanation of the top-emitting element, please refer to the explanation of the top-emitting element shown in Figure 3 in the previous paragraph.

[0065] According to one embodiment of the present invention, the maximum emission wavelength of the electroluminescence spectrum of the metal complex is λ max and the full width at half maximum is FWHM, provided that 490 nm≦λ max ≦524 nm and FWHM≦35 nm.

[0066] In this specification, the "electroluminescence spectrum" in the "electroluminescence spectrum of the metal complex" refers to the emission spectrum of any bottom-emission device containing the metal complex. The "bottom-emission device" includes, but is not limited to, the following bottom-emission devices used in this application: An 80-nm-thick ITO layer was evaporated and used as the anode; Compound HI was used as the HIL and had a thickness of 100 Å; Compound HT was used as the HTL and had a thickness of 350 Å; Compound PH-23 was used as the EBL and had a thickness of 50 Å; a metal complex, Compound PH-23, and Compound H-40 (weight ratio 6:56:38) were co-evaporated and used as the emitting layer (EML) and had a thickness of 400 Å; Compound H-2 was evaporated and used as the HBL and had a thickness of 50 Å; and Compound ET and Liq (weight ratio 40:60) were co-evaporated and used as the ETL and had a thickness of 350 Å. A 1 nm thick Liq is evaporated and used as the EIL. 120 nm thick aluminum is evaporated and used as the cathode. The specific structure of the above compound is shown in the device example below. The above specific bottom-emitting device is merely illustrative. Those skilled in the art can adjust the thickness of any layer, use appropriate material combinations and interlocking for any layer, and even increase or decrease some functional layers as needed to adjust the bottom-emitting device.

[0067] According to one embodiment of the present invention, the metal complex has an electroluminescence spectrum with a maximum emission wavelength of λ max and the full width at half maximum is FWHM, provided that 500 nm≦λ max ≦524 nm and FWHM≦34 nm.

[0068] According to one embodiment of the present invention, D≦0.0280.

[0069] According to one embodiment of the present invention, the highest occupied molecular orbital energy level (E HOMO ) is less than -5.05 eV.

[0070] According to one embodiment of the present invention, the highest occupied molecular orbital energy level (E HOMO ) is less than -5.10 eV.

[0071] According to one embodiment of the present invention, the highest occupied molecular orbital energy level (E HOMO ) is less than -5.20 eV.

[0072] According to one embodiment of the present invention, the lowest unoccupied molecular orbital energy level (E LUMO ) is less than -2.1 eV.

[0073] According to one embodiment of the present invention, the lowest unoccupied molecular orbital energy level (E LUMO ) is less than -2.2 eV.

[0074] According to one embodiment of the present invention, the lowest unoccupied molecular orbital energy level (E LUMO ) is less than -2.3 eV.

[0075] According to an embodiment of the present invention, the organic layer further comprises a first compound.

[0076] According to one embodiment of the present invention, the lowest unoccupied molecular orbital energy level (E LUMO-H1 ) is less than -2.70 eV.

[0077] According to one embodiment of the present invention, the lowest unoccupied molecular orbital energy level (E LUMO-H1 ) is less than -2.80 eV.

[0078] According to an embodiment of the present invention, the organic layer further comprises a first compound and a second compound.

[0079] According to one embodiment of the present invention, the highest occupied molecular orbital energy level (E HOMO-H2 ) is greater than -5.60 eV.

[0080] According to one embodiment of the present invention, the highest occupied molecular orbital energy level (E HOMO-H2 ) is greater than -5.50 eV.

[0081] According to one embodiment of the present invention, the first compound and / or the second compound comprises at least one chemical group selected from the group consisting of benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, siliconfluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

[0082] According to one embodiment of the present invention, the metal complex is doped into the first compound and the second compound, and the weight of the metal complex is 1% to 30% based on the total weight of the organic layer.

[0083] According to one embodiment of the present invention, the metal complex is doped into the first compound and the second compound, and the weight of the metal complex is 3% to 13% based on the total weight of the organic layer.

[0084] According to one embodiment of the present invention, the organic electroluminescent device is a top-emitting device.

[0085] According to one embodiment of the present invention, the organic electroluminescent element is a top-emitting element, and the maximum emission wavelength of the top-emitting element is λ max and 500 nm≦λ max ≦540 nm.

[0086] According to one embodiment of the present invention, the top emission element is a single layer element or a multi-layer element.

[0087] According to one embodiment of the present invention, the organic electroluminescent device is a bottom emission device.

[0088] According to one embodiment of the present invention, the organic electroluminescent element is a stacked element.

[0089] According to one embodiment of the present invention, the organic electroluminescent element is a laminated element, and the laminated element emits white light.

[0090] According to one embodiment of the present invention, the metal complex is M(L a ) m (L b ) n (L c ) q having the general formula L a , L b and L c are the first, second and third ligands coordinated to the metal M, respectively, and L a , L b , L c are the same or different, L a , L b and L c may be linked to form a tetradentate or polydentate ligand; the metal M at each occurrence is identically or differently selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt; m is selected from 1, 2 or 3, n is selected from 0, 1 or 2, q is selected from 0, 1 or 2, and m+n+q is equal to the oxidation state of M; when m is 2 or 3, multiple L a may be the same or different, and when n is 2, two L b may be the same or different, and when q is 2, two L c may be the same or different, L a has the structure AE, A's each appearing may be the same or different and are selected from substituted or unsubstituted heteroaromatic rings having 5 to 6 ring atoms, the heteroaromatic rings containing at least one nitrogen atom, and A's form a metal-nitrogen bond or a metal-G-nitrogen bond with a metal via the nitrogen atom in the heteroaromatic ring; each occurrence of E may be the same or different and selected from a substituted or unsubstituted aromatic ring having 13 to 30 ring atoms or a substituted or unsubstituted heteroaromatic ring having 13 to 30 ring atoms, the aromatic ring or heteroaromatic ring having a fused structure with at least three rings, the at least three rings including at least two six-membered rings and one five-membered ring, E forms a metal-carbon bond or a metal-G-carbon bond with a metal via a carbon atom in the aromatic ring or heteroaromatic ring, L b and L c has the same or different structure CLD for each occurrence, C and D, each occurrence, may be the same or different and are selected from a substituted or unsubstituted aromatic ring having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic ring having 5 to 30 ring atoms, or a combination thereof; C and D, each occurrence, may be the same or different and form a metal-carbon bond, a metal-nitrogen bond, a metal-G-carbon bond, or a metal-G-nitrogen bond with a metal through a carbon atom or a nitrogen atom in the aromatic ring or heteroaromatic ring; L may be the same or different in each occurrence and may be a single bond, BR L , C.R. L R L , N.R. L , SiR L R L , PR L , GeR L R L , O, S, Se, a substituted or unsubstituted vinylidene group, an acetylene group, a substituted or unsubstituted arylene group having 5 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 30 carbon atoms, and combinations thereof; L When two R L are the same or different, R Leach occurrence may be the same or different and represent hydrogen or a substituent; G, in each occurrence, may be the same or different and is selected from a single bond, O or S; Adjacent substituents may be bonded to form a ring.

[0091] According to one embodiment of the invention, said metals M, identically or differently at each occurrence, are selected from Pt or Ir.

[0092] According to one embodiment of the present invention, the organic layer containing the metal complex is a light-emitting layer.

[0093] According to another object of the present invention, there is further disclosed a display assembly including the organic electroluminescent device described in any one of the above embodiments.

[0094] According to another object of the present invention, further embodiments of metal complexes are disclosed. The disclosed metal complexes are a ) m (L b ) n (L c ) q having the general formula L a , L b and L c are the first, second, and third ligands, respectively, coordinated to the metal M, and L a , L b , L c are the same or different, L a , L b and L c may be linked to form a tetradentate or polydentate ligand; m is selected from 1, 2 or 3, n is selected from 0, 1 or 2, q is selected from 0, 1 or 2, and m+n+q is equal to the oxidation state of M; when m is 2 or 3, multiple L a may be the same or different, and when n is 2, two L b may be the same or different, and when q is 2, two L c may be the same or different, The metal complex comprises a metal M and at least one C^N bidentate ligand L coordinated to the metal M. a and, the metal M is selected from metals with a relative atomic mass greater than 40; L b and L c are the same or different at each occurrence and are selected from monoanionic bidentate ligands, The area ratio of the photoluminescence spectrum of the metal complex at room temperature is AR, and AR≦0.331; When the metal complex has a maximum current efficiency in a top-emitting device, the corresponding color coordinates are CIE(x,y), The distance between the CIE (x, y) and the color coordinates CIE (0.170, 0.797) is D, However, CIEy≧0.797 or D≦0.0320.

[0095] According to one embodiment of the present invention, the metal complex has a structure represented by Formula 1 or Formula 2: [ka] (Metal M is selected from metals having a relative atomic mass greater than 40, Ring A, which may be the same or different at each occurrence, is selected from nitrogen-containing heteroaromatic rings having 5 to 6 ring atoms; Ring E is selected from aromatic or heteroaromatic rings having 13 to 30 ring atoms, each of which may be the same or different and has a fused structure containing at least three rings, and which contains at least two six-membered rings and one five-membered ring; ring C and ring D, each occurrence of which may be the same or different, are selected from an aromatic ring having 6 to 30 carbon atoms, a heteroaromatic ring having 3 to 30 carbon atoms, or a combination thereof; Z, identically or differently at each occurrence, is selected from C or N; G, in each occurrence, may be the same or different and is selected from a single bond, O or S; L, L1 and L2 may be the same or different and represent a single bond, BR L , C.R. L R L , N.R.L , SiR L R L , PR L , GeR L R L , O, S, Se, a substituted or unsubstituted vinylidene group, an acetylene group, a substituted or unsubstituted arylene group having 5 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 30 carbon atoms, and combinations thereof; L When two R L are the same or different, a, b and c are the same or different and selected from 0 or 1 at each occurrence; R a , R e , R c and R d are the same or different at each occurrence and represent mono-, multi- or no substitution; R a , R e , R c , R d and R Lare the same or different at each occurrence and represent hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon atom a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituents R a , R e , R c , R d and R L may be bonded to form a ring.

[0096] In the present specification, "adjacent substituents R a , R e , R c , R d and R L may be bonded to form a ring" means that adjacent substituent groups, for example, two substituents R a two substituents R e two substituents R c two substituents R d two substituents R L R a and R e Rc and R d R c and R L R d and R L R a and R L R e and R L This means that any one or more of the substituents may be linked to form a ring. Obviously, none of these substituents may be linked to form a ring.

[0097] According to one embodiment of the present invention, L b and L c is the same or different at each occurrence and is selected from the group consisting of formulas a to m. [ka] (R A and R B are the same or different at each occurrence and represent mono-, multi- or no substitution; X B are O, S, Se, NR, or the same or different for each occurrence. N1 , C.R. C1 R C2 selected from the group consisting of R A , R B , R C , R D , R N1 , R C1 and R C2are the same or different at each occurrence and represent hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon atom a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituents R A , R B , R C , R D , R N1 , R C1 and R C2 may be bonded to form a ring.

[0098] In the present specification, "adjacent substituents R A , R B , R C , R D , R N1 , R C1 and R C2 may be bonded to form a ring" means that adjacent substituent groups, for example, two substituents R A two substituents R B R A and R B RA and R C R B and R C R A and R N1 R B and R N1 R A and R C1 R A and R C2 R B and R C1 R B and R C2 Comrades and R C1 and R C2 This means that any one or more of the substituents may be bonded to form a ring. Obviously, none of these substituents may be bonded to form a ring. For example, [ka] Adjacent substituents R in A , R B may be bonded to form a ring, R A may be bonded to form a ring, [ka] teeth, [ka] The following structure may be formed.

[0099] According to one embodiment of the present invention, L a each occurrence may be the same or different and have the structure represented by formula 3; L b has the structure represented by Formula 4, which may be the same or different at each occurrence. [ka] A may be the same or different at each occurrence and is selected from nitrogen-containing heteroaromatic rings having 5 to 6 ring atoms; X is selected from the group consisting of O, S, Se, NR', CR'R' and SiR'R', and when two R's are present at the same time, the two R's are the same or different; U1 to U8 are the same or different CRs for each occurrence. u or selected from N, G, in each occurrence, may be the same or different and is selected from a single bond, O or S; X1 to X7 may be the same or different and may be C, N, or CR x and one of X1, X2 and X3 is selected from C and is bonded to A; one of X1, X2 and X3 is selected from N and is bonded to the metal by a metal-nitrogen bond, or one of X1, X2 and X3 is selected from C and is bonded to the metal by G; At least one of X1 to X7 is CR x and wherein R x is a cyano group or fluorine, R a are the same or different at each occurrence and represent mono-, multi- or no substitution; R', R u , R x and R aare the same or different at each occurrence and represent hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon atom a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; R yare the same or different at each occurrence and each represents a halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 3 a substituted or unsubstituted aryl group having from 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having from 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having from 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having from 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having from 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having from 6 to 20 carbon atoms, a substituted or unsubstituted amino group having from 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituents R x may be bonded to form a ring, Adjacent substituents R a may be bonded to form a ring, Adjacent substituents R u may be bonded to form a ring.

[0100] In the present specification, "adjacent substituents R x may be bonded to form a ring" means that any two adjacent substituents R x may be linked to form a ring. Obviously, none of these substituent groups may be linked to form a ring.

[0101] In the present specification, "adjacent substituents R amay be bonded to form a ring" means that any two adjacent substituents R a may be linked to form a ring. Obviously, none of these substituent groups may be linked to form a ring.

[0102] In the present specification, "adjacent substituents R u may be bonded to form a ring" means that any two adjacent substituents R u may be linked to form a ring. Obviously, none of these substituent groups may be linked to form a ring.

[0103] According to one embodiment of the present invention, in Eq. [ka] is selected from any one of the following structures, which may be the same or different at each occurrence: [ka] (R may be the same or different at each occurrence and represent mono-, poly- or unsubstituted, and when multiple R are present in any one structure, said R may be the same or different, R may be the same or different at each occurrence and is hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon atom a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituents R may be bonded to form a ring; "#" indicates the binding site with G, [ka] represents the bonding site to X1, X2 or X3.

[0104] In this specification, the phrase "adjacent substituents R may be bonded to form a ring" means that one or more of any two adjacent substituents R in a substituent group may be bonded to form a ring. Obviously, these substituent groups do not necessarily have to be bonded to form a ring.

[0105] According to one embodiment of the present invention, the metal complex is Ir(L a ) m (L b )3-m and has a structure represented by formula 5. [ka] (m is chosen from 1 or 2, and when m=1, two L b are the same or different, and when m=2, two L a are the same or different, X is selected from the group consisting of O, S, Se, NR', CR'R', SiR'R' and GeR'R', and when two R's are present at the same time, the two R's are the same or different; Y1 to Y4 may be the same or different for each occurrence. Y or selected from N, U1 to U8 are the same or different CRs for each occurrence. u or selected from N, X3 to X7 are the same or different CRs for each occurrence. x or selected from N, At least one of X3 to X7 is CR x and wherein R x is a cyano group or fluorine, R', R x , R Y and R uare the same or different at each occurrence and represent hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon atom a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; R y are the same or different at each occurrence and are selected from the group consisting of fluorine, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, and combinations thereof; Adjacent substituents R Y may be bonded to form a ring, Adjacent substituents R u may be bonded to form a ring.

[0106] In the present specification, "adjacent substituents R Y may be bonded to form a ring" means that any two adjacent substituents R Y may be linked to form a ring. Obviously, none of these substituent groups may be linked to form a ring.

[0107] According to another embodiment of the present invention, X, identically or differently at each occurrence, is selected from O or S.

[0108] According to another embodiment of the present invention, X is O.

[0109] According to one embodiment of the present invention, at least one of X4 to X7 is CR x and wherein R x are the same or different at each occurrence and each represents a halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 3 the alkyl group having from 0 to 20 carbon atoms, a substituted or unsubstituted aryl group having from 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having from 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having from 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having from 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having from 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having from 6 to 20 carbon atoms, a substituted or unsubstituted amino group having from 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

[0110] According to one embodiment of the present invention, at least one of X4 to X7 is CR x and wherein R x are the same or different at each occurrence and are selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, fluorine, a cyano group, or a combination thereof.

[0111] According to one embodiment of the present invention, at least one of X4 to X7 is CR x and wherein R x is a fluorine or cyano group.

[0112] According to one embodiment of the present invention, the X6 x and wherein R x is a fluorine or cyano group.

[0113] According to one embodiment of the present invention, the X7 x and wherein R x is the same or different at each occurrence and is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, fluorine, a cyano group, or a combination thereof.

[0114] According to one embodiment of the present invention, at least one or at least two of U1 to U8 are CR u Selected from and R u is selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a combination thereof, and all of the R u The sum of the carbon atoms is at least 4.

[0115] According to one embodiment of the present invention, at least one or at least two of U5 to U8 are CR u Selected from and R uis selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a combination thereof, and all of the R u The sum of the carbon atoms is at least 4.

[0116] According to one embodiment of the present invention, at least one or at least two of U1 to U4 are CR u Selected from and R u is selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a combination thereof, and all of the R u The sum of the carbon atoms is at least 4.

[0117] According to one embodiment of the present invention, at least one or at least two of U1 to U4 are CR u Selected from and R u is selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a combination thereof, and all of the R u The sum of the carbon atoms of U5 to U8 is at least 4. At the same time, at least one or at least two of U5 to U8 are CR u Selected from and R u is selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a combination thereof, and all of the R u The sum of the carbon atoms is at least 4.

[0118] According to one embodiment of the present invention, U2 or U3 is u Selected from and R u is selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a combination thereof.

[0119] According to one embodiment of the present invention, U2 or U3 is uSelected from and R u is selected from a substituted or unsubstituted alkyl group having 4 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 4 to 20 ring carbon atoms, or a combination thereof.

[0120] According to one embodiment of the present invention, at least one of U1 to U4 is a CR u and at least one of Y1 to Y4 is selected from CR, u R is selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a combination thereof, and R u , the sum of R is 2 or more.

[0121] According to one embodiment of the present invention, at least one of U5 to U8 is a CR u and at least one of Y1 to Y4 is selected from CR, u R is selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a combination thereof, and R u , the sum of R is 2 or more.

[0122] According to one embodiment of the present invention, at least one of U1 to U4 is a CR u At least one of U5 to U8 is selected from CR u wherein R u is selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a combination thereof, and R u The sum of is 2 or more.

[0123] According to one embodiment of the present invention, the metal complex is Ir(L a ) m (L b ) 3-m and has a structure represented by formula 5-1. [ka] (m is chosen from 1 or 2, and when m=1, two L b are the same or different, and when m=2, two L a are the same or different, X is selected from the group consisting of O, S, Se, NR', CR'R', SiR'R' and GeR'R', and when two R's are present at the same time, the two R's are the same or different; X6~X7 are the same or different CRs each time they appear. x or selected from N, R x and R Y are the same or different at each occurrence and represent mono-, multi- or no substitution; At least one R x is a cyano group or fluorine, R', R x , R Yand R1 to R8, each occurrence may be the same or different and each represent hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted selected from the group consisting of aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof, each having 0 to 20 carbon atoms; R y are the same or different at each occurrence and are selected from the group consisting of fluorine, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, and combinations thereof; Adjacent substituents R Y may be bonded to form a ring, Adjacent substituents R1 to R8 may be bonded to form a ring.

[0124] According to one embodiment of the present invention, Ry is selected at each occurrence from the group consisting of substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms and substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms.

[0125] According to one embodiment of the present invention, R y is selected at each occurrence from the group consisting of substituted or unsubstituted alkyl groups having 4 to 20 carbon atoms.

[0126] According to one embodiment of the present invention, R y is selected from the group consisting of the following substituted or unsubstituted substituents and combinations thereof: [ka] The hydrogen atoms in the above groups may be partially or completely deuterated. The symbol "*" indicates the bonding point between the substituent and the carbon.

[0127] According to one embodiment of the present invention, at least one or at least two of R1 to R8 are selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a combination thereof, and the sum of the carbon atoms of all of R1 to R4 and / or R5 to R8 is at least 4.

[0128] According to one embodiment of the present invention, at least one or at least two of R5 to R8 are selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a combination thereof, and the sum of the carbon atoms of all the substituents R5 to R8 is at least 4.

[0129] According to one embodiment of the present invention, at least one or at least two of R1 to R4 are selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a combination thereof, and the sum of the carbon atoms of all the substituents R1 to R4 is at least 4.

[0130] According to one embodiment of the present invention, at least one or at least two of R1 to R4 are selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a combination thereof, and the sum of the carbon atoms of all the substituents R1 to R4 is at least 4. At the same time, at least one or at least two of R5 to R8 are selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a combination thereof, and the sum of the carbon atoms of all the substituents R5 to R8 is at least 4.

[0131] According to one embodiment of the present invention, R2 or R3 is selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a combination thereof.

[0132] According to one embodiment of the present invention, R2 or R3 is selected from a substituted or unsubstituted alkyl group having 4 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 4 to 20 ring carbon atoms, or a combination thereof.

[0133] According to one embodiment of the invention, the metals M, identically or differently at each occurrence, are selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt.

[0134] According to one embodiment of the invention, the metals M, identically or differently at each occurrence, are selected from Pt or Ir.

[0135] According to one embodiment of the invention, A at each occurrence may be identical or different and may be unsubstituted or one or more R a is selected from nitrogen-containing aromatic rings having 6 ring atoms substituted with

[0136] According to one embodiment of the invention, A at each occurrence may be identical or different and may be unsubstituted or one or more R apyridine, unsubstituted or substituted with one or more R a pyrimidine substituted with, or unsubstituted or substituted with one or more R a The compound is selected from triazines substituted with

[0137] According to one embodiment of the invention, E at each occurrence may be identical or different and may be unsubstituted or one or more R e The aromatic ring or heteroaromatic ring has a 6-membered-5-membered-6-membered ring structure and is substituted with

[0138] According to one embodiment of the invention, E at each occurrence may be identical or different and may be unsubstituted or one or more R e and azadibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, fluorene, silicon fluorene, germanium fluorene, azadibenzothiophene, azadibenzofuran, azadibenzoselenophene, azacarbazole, azafluorene, azasilicon fluorene, and azagermanium fluorene, each of which is substituted with

[0139] According to one embodiment of the invention, C at each occurrence may be identical or different and may be unsubstituted or one or more R c Aromatic rings with 6 to 20 ring atoms, unsubstituted or substituted with one or more R c a heteroaromatic ring having 5 to 20 ring atoms substituted with, or a combination thereof.

[0140] According to one embodiment of the invention, C at each occurrence may be identical or different and may be unsubstituted or one or more R c Aromatic rings with 6 to 12 ring atoms, unsubstituted or substituted with one or more R c a heteroaromatic ring having 5 to 12 ring atoms substituted with, or a combination thereof.

[0141] According to one embodiment of the invention, C at each occurrence may be identical or different and may be unsubstituted or one or more R c Benzene ring, unsubstituted or substituted with one or more R ca heteroaromatic ring having 5 to 6 ring atoms substituted with, or a combination thereof.

[0142] According to one embodiment of the invention, D at each occurrence may be identical or different and may be unsubstituted or one or more R d Aromatic rings with 6 to 20 ring atoms, unsubstituted or substituted with one or more R d a heteroaromatic ring having 5 to 20 ring atoms substituted with, or a combination thereof.

[0143] According to one embodiment of the invention, D at each occurrence may be identical or different and may be unsubstituted or one or more R d Aromatic rings with 6 to 12 ring atoms, unsubstituted or substituted with one or more R d a heteroaromatic ring having 5 to 12 ring atoms substituted with, or a combination thereof.

[0144] According to one embodiment of the invention, D at each occurrence may be identical or different and may be unsubstituted or one or more R d Benzene ring, unsubstituted or substituted with one or more R d a heteroaromatic ring having 5 to 6 ring atoms substituted with, or a combination thereof.

[0145] According to one embodiment of the invention, C at each occurrence may be identical or different and may be unsubstituted or one or more R c and C is selected from a pyridine ring, a pyrimidine ring, a pyrazine ring, a pyridazine ring, a triazine ring, an imidazole ring, an imidazole carbene ring, a pyrazole ring, a thiazole ring, and an oxazole ring substituted with

[0146] According to one embodiment of the invention, C at each occurrence may be identical or different and may be unsubstituted or one or more R c The pyridine ring is selected from the group consisting of a pyridine ring substituted with

[0147] According to one embodiment of the invention, D at each occurrence may be identical or different and may be unsubstituted or one or more R dand D is selected from a benzene ring, a pyridine ring, a pyrimidine ring, a pyrazine ring, a pyridazine ring, a triazine ring, an imidazole ring, an imidazole carbene ring, a pyrazole ring, a thiazole ring, and an oxazole ring substituted with

[0148] According to one embodiment of the invention, D at each occurrence may be identical or different and may be unsubstituted or one or more R d is selected from a benzene ring substituted with

[0149] According to one embodiment of the present invention, R a , R e , R c and R d at least one of is deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 ... a substituted or unsubstituted aryl group having from 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having from 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having from 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having from 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having from 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having from 6 to 20 carbon atoms, a substituted or unsubstituted amino group having from 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

[0150] According to one embodiment of the present invention, R a , R e , R c and Rd At least one of is selected from the group consisting of halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a cyano group, and combinations thereof.

[0151] According to one embodiment of the present invention, R a , R e , R c and R d At least one of is selected from the group consisting of fluorine, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 18 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 12 carbon atoms, a cyano group, and combinations thereof.

[0152] According to one embodiment of the present invention, R c At least one of, and / or R d At least one of these is selected from the group consisting of substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms and substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms.

[0153] According to one embodiment of the present invention, R c At least one of, and / or R d At least one of the groups is selected from the group consisting of substituted or unsubstituted alkyl groups having 4 to 10 carbon atoms and substituted or unsubstituted cycloalkyl groups having 4 to 10 ring carbon atoms.

[0154] According to one embodiment of the present invention, R c is selected from the group consisting of substituted or unsubstituted alkyl groups having 4 to 10 carbon atoms and substituted or unsubstituted cycloalkyl groups having 4 to 10 ring carbon atoms, and R dOne of the groups is selected from the group consisting of substituted or unsubstituted alkyl groups having 4 to 10 carbon atoms and substituted or unsubstituted cycloalkyl groups having 4 to 10 ring carbon atoms.

[0155] According to one embodiment of the present invention, R e At least one of is selected from F or CN.

[0156] According to one embodiment of the present invention, R e At least one of is selected from F or CN, and R e At least one of the groups is selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, and combinations thereof.

[0157] According to one embodiment of the present invention, R e At least one of is selected from F or CN, and R e At least one of the groups is selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a combination thereof.

[0158] According to another embodiment of the present invention, L b and L c may be the same or different for each occurrence, [ka] [ka] [ka] [ka] is selected from the group consisting of:

[0159] According to one embodiment of the present invention, the L b1 ~L b147 The hydrogen atoms in may be partially or completely deuterated.

[0160] According to one embodiment of the present invention, said metal complexes are selected from the group consisting of Metal Complex 1 to Metal Complex 61, which may be the same or different at each occurrence. [ka] [ka] [ka] [ka] [ka] [ka]

[0161] According to one embodiment of the present invention, the hydrogen atoms in Metal Complex 1 to Metal Complex 61 may be partially or completely deuterated.

[0162] According to another object of the present invention, the application of the metal complex in a photoelectric device is further disclosed, and the metal complex can be any one of the above-mentioned embodiments.

[0163] According to one embodiment of the present invention, the first compound has a structure represented by Formula 6: [ka] (E1 to E6 are the same or different for each occurrence. E or N, wherein at least two of E1 to E6 are N, and at least one of E1 to E6 is C, and is bonded to formula A; [ka] Q may be the same or different for each occurrence and may be O, S, Se, N, or NR Q , C.R. Q R Q , SiR Q R Q , GeR Q R Q and R Q C=CR Q and two R Q When two R Q may be the same or different, p is 0 or 1, r is 0 or 1, When Q is selected from N, p is 0 and r is 1; Q is O, S, Se, or NR Q , C.R. Q R Q , SiR Q R Q , GeR Q R Q and R Q C=CR Q When selected from the group consisting of: p is 1 and r is 0; L q are the same or different at each occurrence and are selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof; Q1 to Q8 are the same or different for each occurrence. q or selected from N, R E , R Q and R qare the same or different at each occurrence and represent hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon atom a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; "*" represents the bond between Formula A and Formula 6, Adjacent substituents R E , R Q , R q may be bonded to form a ring.

[0164] In the present specification, "adjacent substituents R E , R Q , R q may be bonded to form a ring" means that adjacent substituent groups, for example, two substituents R E two substituents R Q two substituents R q two substituents R Q and R q This means that any one or more of these substituents may be bonded to form a ring. Obviously, none of these substituents may be bonded to form a ring.

[0165] According to one embodiment of the present invention, the first compound is selected from the group consisting of the following compounds: [ka] [ka] [ka] [ka] [ka] [ka]

[0166] According to one embodiment of the present invention, the second compound has a structure represented by formula X-1 or X-2. [ka] (L x are the same or different at each occurrence and are selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof; G may be identical or different for each occurrence of C(R g )2, NR g , O or S; V may be the same or different for each occurrence. v or selected from N, In formula X-1, T may be the same or different at each occurrence and may be C, CR t or selected from N, In formula X-2, T may be the same or different for each occurrence. t or selected from N, Rg , R v and R t are the same or different at each occurrence and represent hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 2 to 2 ... a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Ar1, which may be the same or different at each occurrence, is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof; Adjacent substituents R g , R v and R t may be bonded to form a ring.

[0167] In the examples, "adjacent substituents R g , R v and R t may be bonded to form a ring" means that adjacent substituent groups, for example, two substituents R v two substituents R t two substituents R g R v and R t R v and R g R gand R t This means that any one or more of these substituents may be bonded to form a ring. Obviously, none of these substituents may be bonded to form a ring.

[0168] According to one embodiment of the present invention, the second compound has a structure represented by one of Formulas Xa to Xp. [ka] (L x are the same or different at each occurrence and are selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof; G may be identical or different for each occurrence of C(R g )2, NR g , O or S; V may be the same or different for each occurrence. v or selected from N, T may be the same or different for each occurrence. t or selected from N, R g , R v and R tare the same or different at each occurrence and represent hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 2 to 2 ... a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Ar1, which may be the same or different at each occurrence, is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof; Adjacent substituents R g , R v and R t may be bonded to form a ring.

[0169] According to one embodiment of the present invention, the second compound is selected from the group consisting of the following compounds: [ka] TIFF0007769399000038.tif55168 [ka] [ka]

[0170] According to one embodiment of the present invention, in the electroluminescent device, the first compound and the second compound are doped with a metal complex, and the weight of the metal complex is 1% to 30% of the total weight of the light-emitting layer.

[0171] According to one embodiment of the present invention, in the electroluminescent device, the first compound and the second compound are doped with a metal complex, and the weight of the metal complex is 3% to 13% of the total weight of the light-emitting layer.

[0172] According to one embodiment of the present invention, the organic electroluminescent device further includes a hole injection layer, which may be a functional layer of a single material or a functional layer containing multiple materials. Among the multiple materials included, a hole transport material doped with a certain percentage of a p-type conductive dopant is most commonly used. Common p-type dopant materials are as follows: [ka]

[0173] According to one embodiment of the present invention, there is disclosed a display assembly including an organic electroluminescent device according to any one of the above embodiments.

[0174] Combination with other materials

[0175] The materials of the specific layers used in the organic light-emitting devices described in the present invention can be used in combination with various other materials present in the device. These combinations of materials are described in detail in paragraphs 0132 to 0161 of U.S. Patent Application No. US2016 / 0359122A1, the contents of which are incorporated herein by reference in their entirety. The materials described or referenced are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily refer to the literature to identify other materials that can be used in combination.

[0176] It is stated herein that the materials of specific layers used in organic light-emitting devices can be used in combination with various other materials present in the device. Illustratively, the light-emitting dopants disclosed herein can be used in combination with various hosts, transport layers, blocking layers, injection layers, electrodes, and other possible layers. These material combinations are described in detail in paragraphs 0080 to 0101 of patent application US2015 / 0349273A1, the contents of which are incorporated herein by reference in their entirety. The materials described or mentioned are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily refer to the literature to identify other materials that can be used in combination.

[0177] In the material synthesis examples, all reactions were carried out under nitrogen protection unless otherwise specified. All reaction solvents were anhydrous and used as obtained commercially. The synthesized products were subjected to structural confirmation and property testing using one or more instruments commonly used in the art (including, but not limited to, a Bruker nuclear magnetic resonance spectrometer, a Shimadzu liquid chromatography, a liquid chromatography / mass spectrometer, a gas chromatography / mass spectrometer, and a differential scanning calorimeter, a Shanghai Liang Optoelectronics fluorescence spectrophotometer, a Wuhan Science & Technology electrochemical work station, and an Anhui Beike sublimation apparatus) in a manner familiar to those skilled in the art. In the device examples, the device properties were also tested using instruments commonly used in the art (including, but not limited to, an evaporator from Angstrom Engineering, an optical test system and a service life test system from Suzhou Fusida, and an ellipsometer from Beijing Liangtuo) in a manner familiar to those skilled in the art. Those skilled in the art are familiar with the relevant content, such as the use of the above-mentioned equipment and test methods, and can reliably and unaffectedly obtain specific data of the sample, so the above-mentioned relevant content will not be repeated in this specification.

[0178] In the present invention, the emission spectrum area ratio is calculated as follows.

[0179] First, the photoluminescence (PL) spectrum data of the compound to be measured was measured using a fluorescence spectrophotometer, model number F98, manufactured by Shanghai Liang Optoelectronics Co., Ltd. The compound to be measured was dissolved in HPLC-grade toluene at a concentration of 1 x 10 -6 After preparing a solution of 1000 mol / L, the emission spectrum was measured at room temperature (298 K) by exciting it with light at any one of wavelengths within ±30 nm of the maximum wavelength absorption peak. max It has.

[0180] Thereafter, the emission spectrum data is normalized (normalization is performed by dividing all emission intensity data by the maximum value of the emission intensities), and the emission area ratio is calculated according to the following method.

[0181] The maximum radiation wavelength is λ max and 490 nm≦λ max If the radiance is <580 nm, the calculation range is 500 nm to 650 nm. After normalizing the spectrum, the area under the spectral curve where the radiance is greater than 0.02 is integrated to obtain Area 1-1. The length between 500 nm and 650 nm is multiplied by the height between 0.02 and 1.00 to obtain Area 1-2, which is 147. Emission spectrum area ratio = [Area 1-1] / [Area 1-2] = [Area 1-1] / 147 = AR.

[0182] For the calculation of the emission spectrum area ratio, please refer to Figure 5. Figure 5 shows a schematic diagram for calculating the emission spectrum area ratio, in which the emission spectrum is the normalized photoluminescence spectrum. Its maximum emission wavelength is λ max If the wavelength range is within the range of [Area 1-1], the emission area ratio is calculated according to the method described above. The area of ​​the dark part under the curve is Area 1-1, and the area of ​​the rectangle covered by the short black line is Area 1-2. In this case, AR is [Area 1-1] / [Area 1-2].

[0183] Taking metal complex 17 of the present invention as an example, its maximum emission wavelength was measured to be 520 nm. After normalizing its spectrum, the area under the spectral curve with a radiance greater than 0.02 was integrated to obtain Area 1-1, which was 47.222. Multiplying the length between 500 nm and 650 nm by the height between 0.02 and 1.00 yielded Area 1-2, which was 147. The emission spectrum area ratio AR = [Area 1-1] / [Area 1-2] = 47.222 / 147 = 0.321.

[0184] Table 1 shows the calculated data of the maximum emission wavelengths and emission spectrum area ratios of the photoluminescence spectra of some of the metal complexes in the present application and the compounds in the comparative examples.

[0185] [Table 1]

[0186] The metal complexes described above are shown below. [ka]

[0187] The electrochemical properties of the compounds, the highest occupied molecular orbital energy level and the lowest unoccupied molecular orbital energy level, were both measured by cyclic voltammetry (CV). A CorrTest CS120 electrochemical station manufactured by Wuhan Science Instruments Co., Ltd. was used for the measurements, and a three-electrode working system was used, with 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 DMF was used as the solvent, and 0.1 mol / L tetrabutylammonium hexafluorophosphate was used as the supporting electrolyte. The compounds to be measured were dissolved in 10 -3A 100 mol / L solution was prepared, and prior to testing, nitrogen gas was introduced into the solution for 10 minutes to remove oxygen. The instrument parameters were set as follows: scan rate 100 mV / s, potential interval 0.5 mV, oxidation potential test window 0 V to 1 V, reduction potential test window -1 V to -2.9 V. The energy levels of the metal complexes and some compounds used in this application are shown in the table below.

[0188] TIFF0007769399000044.tif100168

[0189] Electroluminescence Spectroscopic Examination of Metal Complexes

[0190] Example 1

[0191] First, a glass substrate with an 80 nm thick indium tin oxide (ITO) anode was cleaned and then treated with oxygen plasma and UV ozone. After treatment, the substrate was dried in a glove box to remove water. The substrate was then mounted on a substrate holder and placed in a vacuum chamber. Hereinafter, for the specified organic layers, a vacuum of approximately 10°C was used. -6 In the case of a 1000-kJ / s device, the layers were sequentially deposited on an ITO anode by hot vacuum evaporation at a rate of 0.01 to 10 Å / s. Compound HI was used as a hole-injection layer (HIL). Compound HT was used as a hole-transport layer (HTL). Compound PH-23 was used as an electron-blocking layer (EBL). Metal complex 17, compound PH-23, and compound H-40 were then co-deposited to form an emissive layer (EML). Compound H-2 was used as a hole-blocking layer (HBL) on the EML. Compound ET and 8-hydroxyquinoline-lithium (Liq) were co-deposited on the HBL to form an electron-transport layer (ETL). Finally, a 1-nm-thick layer of 8-hydroxyquinoline-lithium (Liq) was deposited to form an electron-injection layer, and 120 nm of aluminum was deposited to form a cathode. The device was then transferred to a glove box and encapsulated with a glass cover to complete the device.

[0192] Example 2

[0193] The embodiment of Example 2 is the same as Example 1, except that Metal Complex 32 of the present invention replaces Metal Complex 17 of the present invention in the light-emitting layer.

[0194] Example 3

[0195] The embodiment of Example 3 is the same as Example 1, except that Metal Complex 23 of the present invention replaces Metal Complex 17 of the present invention in the light-emitting layer.

[0196] Comparative Example 1

[0197] The embodiment of Comparative Example 1 is the same as that of Example 1, except that Metal Complex 17 of the present invention is replaced with GD1 in the light-emitting layer.

[0198] Comparative Example 2

[0199] The embodiment of Comparative Example 2 is the same as that of Example 1, except that Metal Complex 17 of the present invention is replaced with GD2 in the light-emitting layer.

[0200] Comparative Example 3

[0201] The embodiment of Comparative Example 3 is the same as Example 1, except that Metal Complex 17 of the present invention is replaced with GD3 in the light-emitting layer.

[0202] Comparative Example 4

[0203] The embodiment of Comparative Example 4 is the same as Example 1, except that Metal Complex 17 of the present invention is replaced with GD4 in the light-emitting layer.

[0204] Comparative Example 5

[0205] The embodiment of Comparative Example 5 is the same as Example 1, except that Metal Complex 17 of the present invention is replaced with GD5 in the light-emitting layer.

[0206] Comparative Example 6

[0207] The embodiment of Comparative Example 6 is the same as Example 1, except that Metal Complex 17 of the present invention is replaced with GD6 in the light-emitting layer.

[0208] Comparative Example 7

[0209] The embodiment of Comparative Example 7 is the same as Example 1, except that Metal Complex 17 of the present invention is replaced with GD7 in the light-emitting layer.

[0210] The detailed layer structure and thickness of the device are shown in the table below: Layers using more than one material are obtained by doping different compounds in the weight ratios mentioned above.

[0211] [Table 2]

[0212] The structure of the material used in the device is shown below. [ka]

[0213] The IVL characteristics of the element were measured. 2 Below, the CIE data of the element, maximum emission wavelength λ MAX The full width at half maximum (FWHM) was measured and these data are recorded and shown in Table 3.

[0214] [Table 3]

[0215] summary

[0216] As can be seen from Table 3, the λ MAXThe λ (i.e., the maximum emission wavelength of the electroluminescence spectrum of the metal complex) was 522 nm, which was smaller than 524 nm, and the full width at half maximum (FWHM) was 30.1 nm, 31.0 nm, and 32.3 nm, respectively, which were all clearly smaller than 34.7 nm. The metal complexes used in Comparative Examples 1 to 3 have skeletons similar to those of the metal complexes in Examples 1 to 3, and their λ MAX The λ values ​​were 532 nm, 531 nm, and 531 nm, respectively, and the FWHMs were 35.8 nm, 34.7 nm, and 57.6 nm, respectively. Each had a different degree of red shift compared to Examples 1 to 3, and the FWHM was broadened. In particular, the FWHM in Comparative Example 3 was broadened by more than 20 nm. MAX Although all of them achieved more saturated green emission at 525 nm, their FWHMs were both broad, at 58.7 nm and 59.4 nm, respectively. Comparative Examples 6 and 7 also have skeletons similar to those of the metal complexes used in Examples 1 to 3, and their λ MAX The wavelengths were all 531 nm, with FWHMs of 58.0 nm and 59.0 nm, respectively, and all had different degrees of red shift compared to Examples 1 to 3, and the FWHMs were wider by more than 23 nm.

[0217] At the same time, the peak areas AR of the metal complexes used in Examples 1 to 3 were 0.321, 0.330, and 0.331, respectively, all of which were 0.331 or less. The peak area ratios of the metal complexes used in the comparative examples were all greater than 0.331, and the peak area ratio AR of the metal complex GD2 used in Comparative Example 2 was 0.332, and although it had the same skeleton as the metal complex used in the examples, the luminescence performance of Examples 1 to 3 was also significantly superior to that of Comparative Example 2.

[0218] As can be seen from this, in Examples 1 to 3, λ MAXhas a clear blue shift and narrower FWHM than Comparative Examples 1 to 7, and Examples 1 to 3 all have CIEx smaller than 0.300 and CIEy larger than 0.650, while Comparative Examples 1 to 7 show the opposite. Therefore, Examples 1 to 3 are shown to have more saturated emission.

[0219] Example of a top-emitting device:

[0220] To study the performance of metal complex devices when they most closely meet the BT.2020 light-emitting requirements, the microcavity of the following top-emission device was adjusted so that the device's CIEx was 0.170, and the device's performance was recorded at this time. At the same time, to examine whether the device's performance when approaching the BT.2020 light-emitting requirements reaches its optimum performance and any discrepancies from the optimum performance, the microcavity of the following top-emission device was adjusted so that the device reached its maximum current efficiency, and the device's performance was recorded at this time. As explained above for the top-emission devices, because the refractive indices of different metal complexes are different, the lengths of the microcavities of top-emission devices containing these different metal complexes are slightly different, i.e., the thicknesses of the HTLs are slightly different.

[0221] Example 4: Metal complex 17 was applied to a top-emission device, specifically as follows.

[0222] First, a 0.7 mm thick glass substrate with a pre-patterned indium tin oxide (ITO) 75 Å / Ag 1500 Å / ITO 150 Å was used as the anode, where the 150 Å ITO deposited on the Ag served as the hole injection function. The substrate was then dried in a glove box to remove moisture, attached to a holder, and placed in a vacuum chamber. Hereinafter, for the specified organic layers, a vacuum of approximately 10 -6At Torr, the layers were deposited sequentially on the anode by hot vacuum evaporation at rates of 0.01–10 Å / s. First, compounds HT and PD were co-evaporated to form a hole injection layer (HIL, 97:3, 100 Å). Compound HT was then deposited on the HIL to form a hole transport layer (HTL, which simultaneously served as a microcavity control layer, controlling the microcavity to within 1000–1500 Å). Compound PH-23 was then deposited on the hole transport layer to form an electron blocking layer (EBL, 50 Å). Metal complex 17, compound PH-1, and compound H-40 were co-evaporated to form an emissive layer (EML, 4:48:48, 400 Å), compound H-2 was co-evaporated to form a hole-blocking layer (HBL, 50 Å), compounds ET and Liq were co-evaporated to form an electron-transporting layer (ETL, 40:60, 350 Å), 10 Å of metal Yb was co-evaporated to form an electron-injection layer (EIL), and metals Ag and Mg were co-evaporated in a 9:1 ratio to form a cathode (140 Å), and compound CP (compound CP has a refractive index of approximately 2.01 at 530 nm) was co-evaporated to a thickness of 800 Å to form a capping layer. The device was then transferred to a glove box and encapsulated in a glass cover under a nitrogen gas atmosphere to complete the device. Among them, the microcavity is adjusted to about 1410 Å (i.e., the thickness of the HTL is about 1410 Å) to achieve the CE of the device. max The microcavity was adjusted to about 1370 Å, and the CIEx of the device was found to be 0.170. max2 obtained.

[0223] Example 5

[0224] The embodiment of Example 5 is the same as Example 4, except that in the light-emitting layer, the metal complex 32 of the present invention is used instead of the metal complex 17 of the present invention. max The microcavity was adjusted to about 1340 Å, and the CIEx of the device was found to be 0.170. max2 obtained.

[0225] Comparative Example 8

[0226] The embodiment of Comparative Example 8 is the same as that of Example 4, except that the metal complex 17 of the present invention is replaced with GD2 in the light-emitting layer. max The microcavity was adjusted to about 1410 Å, and the CIEx of the device was found to be 0.170. max2 obtained.

[0227] The structure and thickness of some layers of the device are given in the table below: More than one material is used, obtained by doping with different compounds in the weight ratios given above.

[0228] [Table 4]

[0229] The structure of the new material used in the device is shown below: [ka]

[0230] The IVL characteristics of the device were measured. 2 The top emission element has the maximum current efficiency (CE max ) when the external quantum efficiency (EQE max ), CIE(x,y), the calculated distance D, and 10 mA / cm 2 When the CIEx in the color coordinate CIE(x,y) is 0.170 under a constant current of max2 , external quantum efficiency (EQE max2 ), C.E. max2 and CE max The ratio of these values ​​was recorded and is shown in Table 5.

[0231] [Table 5]

[0232] summary

[0233] As can be seen from Table 5, the luminescent materials used in Examples 4 and 5 were metal complexes 17 and 32 of the present invention, and had emission spectrum area ratios of 0.321 and 0.331, respectively, both of which were 0.331 or less. The luminescent material GD2, which had the same skeleton as the luminescent material of the present invention and was used in Comparative Example 8, had an emission spectrum area ratio of 0.332.

[0234] As can be seen from the electroluminescence spectrum test of the metal complex in Table 3, the light-emitting material EL of the present invention used in Examples 4 and 5 has a λ MAX The luminescent material EL used in Comparative Example 2, which has the same skeleton as the luminescent material of the present invention, has a λ of 522 nm, which is smaller than 524 nm, and the full width at half maximum (FWHM) is 30.1 nm and 31.0 nm, which is smaller than 34.7 nm. MAX The λ of Comparative Example 2 is 531 nm and the full width at half maximum (FWHM) is 34.7 nm compared to Examples 4 and 5. MAX All of them had a clear red shift and a broadened half-width.

[0235] As can be seen from Table 5, the light-emitting materials of the present invention used in Examples 4 and 5 have the following properties: max The distances D between the color coordinates CIE (x, y) when the graph is taken and the green light color coordinates CIE (0.170, 0.797) of BT.2020 are 0.0219 and 0.0178, respectively, both of which are smaller than 0.0300, and the distance D of the luminescent material having the same skeleton as the luminescent material of the present invention used in Comparative Example 8 is 0.0614. Therefore, the distances from the green light color coordinates CIE (0.170, 0.797) of BT.2020 in Examples 4 and 5 are clearly closer than in Comparative Example 8, indicating that they have more saturated green light emission and wider BT.2020 coverage.

[0236] As can be seen from Table 5, the maximum CE of Comparative Example 8max The maximum external quantum efficiency EQE of Comparative Example 8 reached 194 cd / A, which was 21.3% and 12.1% higher than those of Examples 4 and 5 (160 cd / A, 173 cd / A). max reached 43.77%, which was 13.1% and 3.5% higher than those of Examples 4 and 5, respectively. max2 is only 147cd / A, and CE max The CE of Examples 4 and 5 was reduced by 24.22%. max2 The EQE of Comparative Example 8 was 9 cd / A and 24 cd / A lower than the previous values ​​(156 cd / A, 171 cd / A), which was a decrease of 5.8% and 14.0%. max2 is only 35.45%, and EQE max The EQE of Examples 4 and 5 was 8.32% lower than that of Examples 4 and 5. max2 were 2.55% and 5.84% lower, respectively.

[0237] At the same time, the maximum CE of Examples 4 to 5 max When x=0.170, the green light color coordinates of BT.2020 are CIE (0.170, 0.797), the obtained CE max2 The difference is only 4cd / A and 2cd / A, CE max2 And ultimately CE max The results were 97.50% and 98.84%. max2 and CE max The small difference in CE is advantageous for the use of BT.2020 green phosphorescent material in devices, as it not only achieves a more saturated green light emission but also the maximum CE of BT.2020 green light emission, which is extremely difficult to achieve. max and EQE max is high, but when applied to a BT.2020 element (i.e., when CIEx is 0.170), CE max2 and EQE max2 Therefore, the metal complex of the present invention has excellent performance in the green light emitting device of BT.2020, with more saturated green light emission and higher efficiency.

[0238] In summary, when applied to devices, the metal complexes of the present invention have higher device efficiency and more saturated green emission than metal complexes that do not satisfy the radiation distance D and spectral area ratio AR, and achieve performance that more closely approaches the commercially required BT.2020 requirements, and have broader commercial application prospects.

[0239] Example of simulated top emission element

[0240] In the present invention, the device structure shown in FIG. 4 was combined and simulation was performed using semiconductor thin film optical simulation software Setfos 5.0 manufactured by FLUXiM.

[0241] Simulation Example 1

[0242] The same structure of the device as in Example 4 was designed using Setfos 5.0 semiconductor thin film optical simulation software manufactured by FLUXiM Co., Ltd., and the PL spectrum data of the metal complex 17 of the present invention was input into the simulation software to perform simulation calculations.

[0243] Simulation Example 2

[0244] The same structure of the device as in Example 5 was designed using Setfos 5.0 semiconductor thin film optical simulation software manufactured by FLUXiM Co., Ltd., and the PL spectrum data of the metal complex 32 of the present invention was input into the simulation software to perform simulation calculations.

[0245] Simulated comparative example 1

[0246] Using Setfos 5.0 semiconductor thin film optical simulation software manufactured by FLUXiM, the same structure of the element as in Comparative Example 8 was designed, and the PL spectrum data of GD2 was input into the simulation software to perform simulation calculations.

[0247] Through the tests of the above-mentioned simulated examples and comparative examples, the correspondence relationship between the current efficiency (CE) of one group and the color coordinates CIE (x, y) can be obtained. maxthe corresponding color coordinates CIE(x,y) when the above is taken, the distance D from the calculated BT.2020 green light color coordinates CIE(0.170,0.797), and the current efficiency CE of the simulated element when the CIEx of the color coordinates CIE(x,y) is 0.170. max2 , C.E. max2 and CE max The ratios are recorded and shown in Table 6.

[0248] [Table 6]

[0249] summary

[0250] As can be seen from Table 6, in the simulated examples 1 and 2 and the simulated comparative example 1, the maximum CE max When taking the D value and CE max2 / CE max The values ​​have the same rule as the measured values ​​recorded in Table 5 above, that is, in the measured top emission element examples, the D value of Comparative Example 8 > the D value of Example 5 > the D value of Example 6, and similarly, in the simulated element examples, the D value of simulated Comparative Example 1 > the D value of simulated Example 1 > the D value of simulated Example 2. At the same time, CE max2 / CE max also reached a similar conclusion.

[0251] In summary, the device data obtained by the method of the simulated device example used in this application is shown to be consistent with the results of data obtained from the actual measured structure, and therefore the device data obtained by the method has a significant guiding effect on further research.

[0252] Furthermore, the following elements were simulated:

[0253] Simulation Example 3

[0254] The simulation form of Simulation Example 3 is the same as Simulation Example 1, except that the PL spectrum data of Metal Complex 23 of the present invention is substituted for the PL spectrum data of Metal Complex 17 of the present invention and input into simulation software to perform simulation calculations.

[0255] Simulated comparative example 2

[0256] The simulation form of Simulation Comparative Example 2 is the same as Simulation Example 1, except that the PL spectrum data of GD1 is substituted for the PL spectrum data of Metal Complex 17 of the present invention and input into simulation software to perform simulation calculations.

[0257] Simulated comparative example 3

[0258] The simulation form of Simulation Comparative Example 3 is the same as Simulation Example 1, except that the PL spectrum data of GD3 is substituted for the PL spectrum data of Metal Complex 17 of the present invention and input into simulation software to perform simulation calculations.

[0259] Simulated comparative example 4

[0260] The simulation form of Simulation Comparative Example 4 is the same as Simulation Example 1, except that the PL spectrum data of GD4 is substituted for the PL spectrum data of Metal Complex 17 of the present invention and input into simulation software to perform simulation calculations.

[0261] Simulated comparative example 5

[0262] The simulation form of Simulation Comparative Example 5 is the same as Simulation Example 1, except that the PL spectrum data of GD5 is substituted for the PL spectrum data of Metal Complex 17 of the present invention and input into the simulation software to perform simulation calculations.

[0263] Simulated comparative example 6

[0264] The simulation form of Simulation Comparative Example 6 is the same as Simulation Example 1, except that the PL spectrum data of GD6 is substituted for the PL spectrum data of Metal Complex 17 of the present invention and input into simulation software to perform simulation calculations.

[0265] Simulated comparative example 7

[0266] The simulation form of Simulation Comparative Example 7 is the same as Simulation Example 1, except that the L spectrum data of GD7 is substituted for the PL spectrum data of Metal Complex 17 of the present invention and input into the simulation software to perform simulation calculations.

[0267] Table 7 shows the maximum CE values ​​of the simulated Examples 1 to 3 and the simulated Comparative Examples 1 to 7. max the CIE(x,y) when the value is taken, the distance D from the calculated BT.2020 green light color coordinates CIE(0.170,0.797), and the current efficiency CE of the simulated element corresponding to the CIEx of the color coordinates CIE(x,y) being 0.170. max2 , and C.E. max2 and CE max The ratio of these data is recorded and presented in Table 7.

[0268] [Table 7]

[0269] summary

[0270] As can be seen from Table 7, simulated elements 1 to 3 have a maximum CE max When the values ​​were taken, the D values ​​were 0.0262, 0.0217, and 0.0314, respectively, all of which were smaller than 0.0320, i.e., close to the BT.2020 green light color coordinates CIE (0.170, 0.797). max When the D values ​​were taken, they were 0.0714, 0.0707, 0.0942, 0.0686, 0.0792, 0.0870, and 0.0870, respectively, all of which were larger than 0.0680. This means that the distance between the corresponding CIE(x,y) and the BT.2020 green light color coordinates CIE(0.170,0.797) is large, which causes the green light emission to not saturate and the efficiency to be low.

[0271] As can be seen from Tables 5, 6, and 7, Examples 1 to 3 containing the metal complex of the present invention had smaller distance D values, closer to the green light color coordinate CIE (0.170, 0.797) of BT.2020, resulting in more saturated green light emission, higher device efficiency (CE, EQE), and a smaller color coordinate distance of BT.2020. Comparative Examples 1 to 7 had distance D greater than 0.0680, farther from the green light color coordinate CIE (0.170, 0.797) of BT.2020, resulting in less saturated green light emission and lower device efficiency.

[0272] Simulation Example 4:

[0273] The simulated form of simulated Example 4 was determined based on the photoluminescence spectrum (PL) data of the metal complex 17 of the present invention, with a maximum emission wavelength λ MAX The peak area ratio was 0.170, but the peak width was narrowed to 18 nm to obtain new simulated PL spectrum data, which was the same as in Simulation Example 1. The simulated PL spectrum data was input into the simulation software to form a new simulated example 4.

[0274] The same device structure as in Simulation Example 1 was designed using Setfos 5.0 semiconductor thin film optical simulation software manufactured by FLUXiM. Table 8 shows the CE of Simulation Example 4. max When the color coordinates are taken, the corresponding CIE (x, y) color coordinates are recorded.

[0275] [Table 8]

[0276] summary As can be seen from Table 8, simulated example 4 is CIE y is greater than 0.797, and has wider BT.2020 coverage, allowing for a wider color gamut range, while also improving its CE max reached a high level of 230 cd / A, a significant improvement over the simulated comparative example. yIncreasing σ to greater than 0.797 is theoretically feasible and can result in superior device performance.

[0277] In summary, when a metal complex satisfying the D and AR requirements of the present invention is applied to an organic electroluminescent device, the resulting organic electroluminescent device has higher device efficiency and more saturated green emission than when a metal complex not satisfying the D and AR requirements is applied to an organic electroluminescent device, and can meet the market demand for BT.2020 emission and have high device efficiency under the emission requirements of BT.2020.

[0278] It should be understood that the various embodiments described herein are illustrative only and are not intended to limit the scope of the present invention. Therefore, it will be apparent to those skilled in the art that the invention sought to be protected includes variations on the specific and preferred embodiments described herein. Many of the materials and structures described herein can be substituted with other materials and structures without departing from the spirit of the present invention. It should be understood that the various theories as to why the present invention works are not limiting.

Claims

1. An organic electroluminescent device comprising a cathode, an anode, and an organic layer provided between the cathode and the anode, The organic layer comprises a metal M and at least one C^N bidentate ligand L coordinated with the metal M. ａ and a metal complex comprising the metal M is chosen from metals with a relative atomic mass greater than 40; the area ratio of the photoluminescence spectrum of the metal complex at room temperature is AR, and AR≦0.331; the metal complex has a corresponding color coordinate of CIE (x, y) when it has a maximum current efficiency in a top-emitting device; The distance between the CIE (x, y) and the color coordinates CIE (0.170, 0.797) is D, However, CIEy≧0.797 or D≦0.0320. Organic electroluminescent element.

2. The metal complex has a maximum emission wavelength of λ in the electroluminescence spectrum (EL). ｍａｘ and the full width at half maximum is FWHM, where 490 nm≦λ ｍａｘ ≦524 nm and FWHM≦35 nm; The organic electroluminescence device according to claim 1 .

3. 500 nm≦λ ｍａｘ ≦524 nm and FWHM≦34 nm; The organic electroluminescence device according to claim 2 .

4. D≦0.0280; The organic electroluminescence device according to claim 1 or 2.

5. The highest occupied molecular orbital energy level (E ＨＯＭＯ ) is −5.05 eV or less, The organic electroluminescence device according to claim 1 .

6. The lowest unoccupied molecular orbital energy level (E ＬＵＭＯ ) is −2.1 eV or less, The organic electroluminescence device according to claim 1 .

7. The organic layer further contains a first compound, and the first compound has a lowest unoccupied molecular orbital energy level (E ＬＵＭＯ－Ｈ１ ) is −2.70 eV or less, The organic electroluminescence device according to claim 1 .

8. The organic layer further contains a second compound, and the second compound has a highest occupied molecular orbital energy level (E ＨＯＭＯ－Ｈ２ ) is −5.60 eV or more, The organic electroluminescence device according to claim 7 .

9. the first compound and / or the second compound comprises at least one chemical group selected from the group consisting of benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silicon fluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof; The organic electroluminescence device according to claim 8 .

10. the metal complex is doped into the first compound and the second compound, and the weight of the metal complex is 1% to 30% based on the total weight of the organic layer; The organic electroluminescence device according to claim 8 .

11. The metal complex is M(L ａ ) ｍ (L ｂ ) ｎ (L ｃ ) ｑ having the general formula L ａ , L ｂ and L ｃ are the first, second and third ligands coordinated to the metal M, respectively, and L ａ , L ｂ , L ｃ are the same or different, and L ａ , L ｂ and L ｃ may be linked to form a multidentate ligand; the metal M at each occurrence is identically or differently selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt; m is selected from 1, 2 or 3, n is selected from 0, 1 or 2, q is selected from 0, 1 or 2, m+n+q is equal to the oxidation state of M, and when m is 2 or 3, multiple L ａ may be the same or different, and when n is 2, two L ｂ may be the same or different, and when q is 2, two L ｃ may be the same or different, L ａ has the structure A-E, A's each appearing may be the same or different and are selected from substituted or unsubstituted heteroaromatic rings having 5 to 6 ring atoms, the heteroaromatic rings containing at least one nitrogen atom, and A's forming a metal-nitrogen bond or a metal-G-nitrogen bond with a metal via the nitrogen atom in the heteroaromatic ring; E, each occurrence of which may be the same or different, is selected from a substituted or unsubstituted aromatic ring having 13 to 30 ring atoms or a substituted or unsubstituted heteroaromatic ring having 13 to 30 ring atoms, the aromatic ring or heteroaromatic ring having a fused structure with at least three rings, and the at least three rings include at least two six-membered rings and one five-membered ring, E forms a metal-carbon bond or a metal-G-carbon bond with a metal via a carbon atom in the aromatic ring or heteroaromatic ring, L ｂ and L ｃ has the structure C-L-D, which may be the same or different at each occurrence, C and D, each occurrence, may be the same or different and are selected from a substituted or unsubstituted aromatic ring having 6 to 30 ring atoms, a substituted or unsubstituted heteroaromatic ring having 5 to 30 ring atoms, or a combination thereof; C and D, each occurrence, may be the same or different and form a metal-carbon bond, a metal-nitrogen bond, a metal-G-carbon bond, or a metal-G-nitrogen bond with a metal through a carbon atom or a nitrogen atom in the aromatic ring or heteroaromatic ring; L may be the same or different at each occurrence and represent a single bond, BR Ｌ , C.R. Ｌ R Ｌ , N.R. Ｌ , SiR Ｌ R Ｌ , P.R. Ｌ , GeR Ｌ R Ｌ , O, S, Se, a substituted or unsubstituted vinylidene group, an acetylene group, a substituted or unsubstituted arylene group having 5 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 30 carbon atoms, and combinations thereof; Ｌ When two R Ｌ are the same or different, R Ｌ each occurrence may be the same or different and represent hydrogen or a substituent; G in each occurrence is the same or different and is selected from a single bond, O or S; Adjacent substituents may be bonded to form a ring; The organic electroluminescence device according to claim 1 .

12. the metal M, at each occurrence, is the same or different and is selected from Pt or Ir; The organic electroluminescence device according to claim 1 or 11.

13. The metal complex is Ir(L ａ ) ｍ (L ｂ ) ３－ｍ and having a structure represented by formula 5, 【Chemistry 1】 m is selected from 1 or 2, and when m=1, two L ｂ are the same or different, and when m=2, two L ａ are the same or different, X is selected from the group consisting of O, S, Se, NR', CR'R', SiR'R' and GeR'R', and when two R's are present at the same time, the two R's are the same or different; Y １ ~Y ４ is the same or different for each occurrence Ｙ or N, U １ ~U ８ is the same or different for each occurrence ｕ or N, X ３ ~X ７ is the same or different for each occurrence ｘ or N, X ３ ~X ７ At least one of the following is CR ｘ and wherein R ｘ is a cyano group or fluorine, R', R ｘ , R Ｙ and R ｕ are the same or different at each occurrence and represent hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon atom a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; R ｙ are the same or different at each occurrence and are selected from the group consisting of fluorine, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, and combinations thereof; Adjacent substituents R Ｙ may be bonded to form a ring, Adjacent substituents R ｕ may be bonded to form a ring, The organic electroluminescence device according to claim 1 .

14. the organic layer containing the metal complex is an emitting layer; The organic electroluminescence device according to claim 1 .

15. The organic electroluminescence device according to claim 1, Display assembly.

16. M (L ａ ) ｍ (L ｂ ) ｎ (L ｃ ) ｑ A metal complex having the general formula: L ａ , L ｂ and L ｃ are the first, second and third ligands coordinated to the metal M, respectively, and L ａ , L ｂ , L ｃ are the same or different, and L ａ , L ｂ and L ｃ may be linked to form a multidentate ligand; m is selected from 1, 2 or 3, n is selected from 0, 1 or 2, q is selected from 0, 1 or 2, m+n+q is equal to the oxidation state of M, and when m is 2 or 3, multiple L ａ may be the same or different, and when n is 2, two L ｂ may be the same or different, and when q is 2, two L ｃ may be the same or different, The metal complex comprises a metal M and at least one C^N bidentate ligand L coordinated to the metal M. ａ and, the metal M is chosen from metals with a relative atomic mass greater than 40; L ｂ and L ｃ are the same or different at each occurrence and are selected from monoanionic bidentate ligands, The area ratio of the photoluminescence spectrum of the metal complex at room temperature is AR, and AR≦0.331; the metal complex has a corresponding color coordinate of CIE (x, y) when it has a maximum current efficiency in a top-emitting device; The distance between the CIE (x, y) and the color coordinates CIE (0.170, 0.797) is D, A metal complex, wherein CIEy≧0.797 or D≦0.0320.

17. The metal complex according to claim 16, wherein L a , L b and L c may be bonded to form a tetradentate ring.

18. 17. The metal complex of claim 16, wherein the metal complex has a structure represented by Formula 1 or Formula 2: 【Chemistry 2】 【Transformation 3】 wherein the metal M is selected from metals having a relative atomic mass greater than 40; Ring A, which may be the same or different at each occurrence, is selected from nitrogen-containing heteroaromatic rings having 5 to 6 ring atoms; Ring E is selected from aromatic or heteroaromatic rings having 13 to 30 ring atoms, each of which may be the same or different and which are fused together and have at least three rings, and which contain at least two six-membered rings and one five-membered ring; Ring C and Ring D, each occurrence, are the same or different and are selected from an aromatic ring having 6 to 30 carbon atoms, a heteroaromatic ring having 3 to 30 carbon atoms, or a combination thereof; Z is, identically or differently at each occurrence, selected from C or N; G in each occurrence is the same or different and is selected from a single bond, O or S; L, L １ and L ２ each occurrence may be the same or different and represent a single bond, BR Ｌ , C.R. Ｌ R Ｌ , N.R. Ｌ , SiR Ｌ R Ｌ , P.R. Ｌ , GeR Ｌ R Ｌ , O, S, Se, a substituted or unsubstituted vinylidene group, an acetylene group, a substituted or unsubstituted arylene group having 5 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 30 carbon atoms, and combinations thereof; Ｌ When two R Ｌ are the same or different, a, b and c are the same or different at each occurrence and are selected from 0 or 1; R ａ , R ｅ , R ｃ and R ｄ are the same or different at each occurrence and represent mono-, multi- or no substitution; R ａ , R ｅ , R ｃ , R ｄ and R Ｌ are the same or different at each occurrence and represent hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted carbon atom a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituents R ａ , R ｅ , R ｃ , R ｄ and R Ｌ may be bonded to form a ring.)

19. R ａ , R ｅ , R ｃ and R ｄ at least one of is deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 ... a substituted or unsubstituted aryl group having from 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having from 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having from 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermanium group having from 3 to 20 carbon atoms, a substituted or unsubstituted arylgermanium group having from 6 to 20 carbon atoms, a substituted or unsubstituted amino group, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxyl group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof, each having from 0 to 20 carbon atoms; 19. The metal complex of claim 18.

20. R ａ , R ｅ , R ｃ and R ｄ wherein at least one of is selected from the group consisting of fluorine, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 18 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 12 carbon atoms, a cyano group, and combinations thereof.

21. R ｅ At least one of R is selected from F or CN, and ｅ at least one of which is selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, and combinations thereof; 19. The metal complex of claim 18.

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