organic light-emitting materials

Abstract

To provide a metal complex that serves as a light-emitting material in an emissive layer of an organic electroluminescent device and can greatly improve the efficiency and lifetime of the device.SOLUTION: The present invention discloses, for example, metal complexes that are represented by following formulas and contain a ligand(s) based on isoquinoline which is substituted with deuterium at 3- and 4-position and a ligand(s) based on acetylacetone.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to compounds for use in organic electronic devices, such as organic light-emitting devices, and in particular to organic light-emitting materials containing deuterium-substituted ligands, electroluminescent devices containing the organic light-emitting materials, and combinations of compounds. [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 is applied to the device, green light is 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. Being self-emissive solid-state devices, OLEDs 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] US20150171348A1 (Patent Document 1) discloses a compound having the following partial structure: [ka] Among these, fused ring structures having the following structure are included. [ka] Specific examples include: [ka] It focuses on the change in performance resulting from the introduction of a fused ring structure into the ligand. The application mentions a related complex in which two deuterium atoms are introduced at the 5- and 8-positions of the isoquinoline ring, but does not discuss the deuteration effect, nor does it focus on the change in performance of the metal complex resulting from the introduction of deuterium at the specific 3- and 4-positions of the isoquinoline ring.

[0009] US20080194853A1 (Patent Document 2) discloses an iridium complex having the following structure: [ka] Among them, [ka] is selected from phenylisoquinoline structures, and the ligand X may be selected from acetylacetone-based ligands. Specific examples include: [ka] The inventors of the present application have focused on the improvement in device efficiency resulting from the introduction of multiple deuterium atoms into the iridium complex ligand, but have not focused on the special advantage of introducing hydrogen atoms into two specific positions, the 3- and 4-positions, of the isoquinoline ring, resulting in an improvement in the service life of the device.

[0010] US20030096138A1 (Patent Document 3) discloses an active layer comprising a compound having the following structure: [ka] Among them, the ligand L may be selected from the following structures: [ka] However, R 2 and R 7 ~R 10 are each independently selected from substituents such as H, D, alkyl groups, hydroxyl groups, alkoxy groups, sulfhydryl groups, alkylthio groups, and amine groups, α is 0, 1, or 2, and δ is 0 or an integer from 1 to 4. In the example, α and δ are both 0. In the application, R 2 No examples having a substituent are disclosed, and the effect of introducing a deuterium atom into an iridium complex is not examined.

[0011] WO2018124697A1 (Patent Document 4) discloses an organic electroluminescent compound having the following structure: [ka] wherein R1 to R3 are selected from alkyl groups / deuterated alkyl groups. The inventors of the present application have focused on the improvement in efficiency that the alkyl / deuterated alkyl substituted phenylisoquinoline ligand brings to the iridium complex, but have not focused on the improvement in performance of the metal complex, particularly the service life and efficiency, that is achieved by directly deuterizing the isoquinoline ring.

[0012] US20100051869A1 (Patent Document 5) discloses a composition containing at least one organic iridium complex having a structure represented by the following formula: [ka] The inventors of this application focus on ligands with a 2-carbonylpyrrole structure. While the application mentions perdeuterated phenylisoquinoline ligands, they do not note that they are applied to complexes in combination with acetylacetone-based ligands and that the overall structure is clearly different from that of the metal complexes of the present invention.

[0013] CN109438521A (Patent Document 6) discloses a complex having the following structure: [ka] However, one or more hydrogen atoms in the complex may be replaced by deuterium atoms. The disclosed C^N ligands may have a phenylisoquinoline or phenylquinazoline structure. Specific examples include: [ka] [ka] [ka] The inventors of this application are primarily focused on amidine- and guanidine-based ligands that coordinate at the bis-nitrogen. While the application mentions perdeuterated isoquinoline ligands, it does not note that they are applied to complexes in combination with acetylacetone-based ligands and that the overall structure is clearly different from that of the metal complexes of the present invention. [Prior art documents] [Patent documents]

[0014] [Patent Document 1] U.S. Patent Application Publication No. 2015 / 0171348 [Patent Document 2] U.S. Patent Application Publication No. 2008 / 0194853 [Patent Document 3] U.S. Patent Application Publication No. 2003 / 0096138 [Patent Document 4] International Publication No. 2018 / 124697 [Patent Document 5] U.S. Patent Application Publication No. 2010 / 0051869 [Patent Document 6] Chinese Patent Application Publication No. 109438521 [Non-patent literature]

[0015] [Non-Patent Document 1] Applied Physics Letters, 1987, 51(12):913~915 Summary of the Invention [Problem to be solved by the invention]

[0016] Although iridium complexes containing fully deuterated and doubly deuterated phenylisoquinoline structure ligands at the 5- and 8-positions have been reported in the relevant literature, these examples of deuteration are merely one of many examples of iridium complexes with isoquinoline ligands disclosed in the relevant literature, or do not relate to the use of metal complexes with acetylacetone-based ligands, or do not examine the effects of deuteration and the position of deuteration on device performance, particularly service life, which still needs to be developed in the relevant field. Through serious research, the present inventors have surprisingly discovered that by introducing deuterium atoms into specific positions of the isoquinoline ligands in metal complexes, such metal complexes can be used as light-emitting materials in organic light-emitting devices, significantly improving the efficiency and service life of the devices. [Means for solving the problem]

[0017] Summary of the Invention The present invention provides a series of organic light-emitting materials containing 3,4-deuterium-substituted isoquinoline-based ligands and acetylacetone-based ligands. The compounds can be used as light-emitting materials in the light-emitting layer of organic electroluminescent devices. These novel metal complexes can improve the efficiency and service life of the devices.

[0018] According to one embodiment of the present invention, M(L a ) m (L b ) n (L c ) q Disclosed is a metal complex having a structure represented by the general formula: (L a , L b and L c are the first, second and third ligands, respectively, coordinated with a metal M, where the metal M is a metal having a relative atomic mass greater than 40; L a , L b and L c may be linked to form a multidentate ligand; m is 1 or 2, n is 1 or 2, q is 0 or 1, and m+n+q is equal to the oxidation state of the metal M; If m is greater than 1, L a may be the same or different, and when n is greater than 1, L b may be the same or different, Said first ligand L a has a structure represented by formula 1, [ka] X1 to X4 are the same or different at each occurrence and are selected from CR1 or N; Y1 to Y4 are the same or different at each occurrence and are selected from CR2 or N; R1 and R2 may be the same or different at each occurrence and are selected from the group consisting of 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 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 aryloxy group having 6 to 3 ... 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 amine group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a nitrile group, an isonitrile group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; In formula 1, adjacent substituents may be bonded to form a ring, Said second ligand L b has a structure represented by formula 2, [ka] R t ~R zare the same or different at each occurrence and are selected from the group consisting of 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 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 is selected from the group consisting of unsubstituted 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 amine groups, acyl groups, carbonyl groups, carboxyl groups, ester groups, nitrile groups, isonitrile groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof, each of which has 0 to 20 carbon atoms; In formula 2, adjacent substituents may be bonded to form a ring, Said third ligand L c is a monoanionic bidentate ligand.

[0019] According to another embodiment of the present invention, there is further disclosed an electroluminescent device, including an anode, a cathode, and an organic layer disposed between the anode and the cathode. a ) m (L b ) n (L c ) q The present invention includes metal complexes having a structure represented by the general formula: (L a , L b and L c are the first, second and third ligands, respectively, coordinated with a metal M, where the metal M is a metal having a relative atomic mass greater than 40; L a , L b and L c may be linked to form a multidentate ligand; m is 1 or 2, n is 1 or 2, q is 0 or 1, and m+n+q is equal to the oxidation state of the metal M; If m is greater than 1, L a may be the same or different, and when n is greater than 1, L b may be the same or different, Said first ligand L a has a structure represented by formula 1, [ka] X1 to X4 are the same or different at each occurrence and are selected from CR1 or N; Y1 to Y4 are the same or different at each occurrence and are selected from CR2 or N; R1 and R2 may be the same or different at each occurrence and are selected from the group consisting of 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 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 aryloxy group having 6 to 3 ... 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 amine group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a nitrile group, an isonitrile group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; In formula 1, adjacent substituents may be bonded to form a ring, Said second ligand L b has a structure represented by formula 2, [ka] R t ~R zare the same or different at each occurrence and are selected from the group consisting of 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 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 is selected from the group consisting of unsubstituted 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 amine groups, acyl groups, carbonyl groups, carboxyl groups, ester groups, nitrile groups, isonitrile groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof, each of which has 0 to 20 carbon atoms; In formula 2, adjacent substituents may be bonded to form a ring, Said third ligand L c is a monoanionic bidentate ligand.

[0020] According to another embodiment of the present invention, there is further disclosed a compound formulation comprising the above-described metal complex.

[0021] The metal complexes according to the present invention can be used as light-emitting materials in the light-emitting layer of organic electroluminescent devices. The isoquinoline ligand can be substituted with two deuterium atoms at the 3- and 4-positions and then combined with an acetylacetone ligand to form a metal complex. These metal complexes unexpectedly exhibit numerous properties, including improved device life and external quantum efficiency. The metal complexes can be used to easily fabricate OLEDs, providing electroluminescent devices with high efficiency and long life. [Brief explanation of the drawings]

[0022] [Figure 1]1 is a schematic diagram of an organic light-emitting device that may include a combination of metal complexes and compounds according to the present invention. [Figure 2] 1 is a schematic diagram of another organic light-emitting device that may include a combination of metal complexes and compounds according to the present invention. DETAILED DESCRIPTION OF THE INVENTION

[0023] 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.

[0024] 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.

[0025] 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.

[0026] 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.

[0027] 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.

[0028] 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.

[0029] The materials and structures described herein may also be used in the other organic electronic devices listed above.

[0030] "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 be present between the first and second layers, unless the first layer is specified as being "in contact with" the second layer. Illustratively, the cathode may still be described as being "on" the anode, even if various organic layers are present between the cathode and anode.

[0031] "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.

[0032] 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.

[0033] 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).

[0034] 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.

[0035] 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).

[0036] Definitions of Substituent Terminology

[0037] Halogen or halide, as used herein, includes fluorine, chloro, bromine and iodine.

[0038] The alkyl group includes straight-chain and branched-chain alkyl groups. Specific 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. The alkyl group may also be substituted. Carbon atoms in the alkyl group chain may be replaced with other heteroatoms. Among these, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, and neopentyl are preferred.

[0039] As used herein, the term "cycloalkyl group" includes cyclic alkyl groups. Preferred cycloalkyl groups are those having 4 to 10 ring carbon atoms, including cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, and 2-norbornyl. The cycloalkyl group may be substituted. The carbon atoms in the ring may be substituted with other heteroatoms.

[0040] As used herein, the term "alkenyl group" includes both straight-chain and branched-chain olefinic groups. Preferred alkenyl groups are those having 2 to 15 carbon atoms. Examples of alkenyl groups include vinyl, allyl, 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, and 3-phenyl-1-butenyl. The alkenyl group may also be substituted.

[0041] As used herein, the term "alkynyl group" includes straight-chain and branched-chain alkynyl groups. Preferred alkynyl groups are those having 2 to 15 carbon atoms. The alkynyl group may be substituted.

[0042] As used herein, aryl or aromatic groups encompass both non-fused and fused systems. Preferred aryl groups are those having 6 to 60 carbon atoms, more preferably 6 to 20 carbon atoms, and even more preferably 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, fluorenyl, and naphthalene being preferred. The aryl group may also be substituted. 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.

[0043] As used herein, heterocyclic groups or heterocycles contemplate aromatic and non-aromatic cyclic groups. Isoaryl groups are also referred to as heteroaryl groups. Preferred non-aromatic heterocyclic groups have 3 to 7 ring atoms and contain at least one heteroatom, such as nitrogen, oxygen, or sulfur. The heterocyclic group may also be an aromatic heterocyclic group having at least one heteroatom selected from nitrogen, oxygen, sulfur, and selenium.

[0044] Heteroaryl groups, as used herein, contemplate both non-fused and fused heteroaromatic groups containing 1 to 5 heteroatoms. Preferred heteroaryl groups are those containing 3 to 30 carbon atoms, more preferably 3 to 20 carbon atoms, and even more preferably 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, and benzisoxazole. , benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzofuranpyridine, furodipyridine, benzothienopyridine, thienobipyridine, benzoselenopyridine, and selenobenzopyridine, and preferably includes 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] The alkoxy group is represented by an -O-alkyl group. Examples and preferred examples of the alkyl group are the same as those mentioned above. Examples of the alkoxy group having 1 to 20 carbon atoms, preferably 1 to 6 carbon atoms, include methoxy, ethoxy, propoxy, butoxy, pentyloxy, and hexyloxy. An alkoxy group having 3 or more carbon atoms may be linear, cyclic, or branched.

[0046] 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 mentioned above. Examples of the aryloxy group having 6 to 40 carbon atoms include a phenoxy group and a biphenyloxy group.

[0047] As used herein, an aralkyl group is an alkyl group having an aryl substituent. Aralkyl groups may also be substituted. Examples of aralkyl groups 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, and m-chlorobenzyl. Examples of benzyl 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, of which benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, and 2-phenylisopropyl are preferred.

[0048] The "aza" in azadibenzofuran, aza-dibenzothiophene, 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 readily envision other nitrogen analogs of the above-mentioned aza derivatives, and all of these analogs are defined as being included within the terminology described herein.

[0049] In the present invention, unless otherwise specified, when any of the terms from the group consisting of substituted alkyl group, substituted cycloalkyl group, substituted heteroalkyl group, substituted aralkyl group, substituted alkoxy group, substituted aryloxy group, substituted alkenyl group, substituted aryl group, substituted heteroaryl group, substituted alkylsilyl group, substituted arylsilyl group, substituted amine group, substituted acyl group, substituted carbonyl group, substituted carboxyl group, substituted ester group, substituted sulfinyl group, substituted sulfonyl group, and substituted phosphino group is used, it means that any of the groups from the alkyl group, cycloalkyl group, heteroalkyl group, aralkyl group, alkoxy group, aryloxy group, alkenyl group, aryl group, heteroaryl group, alkylsilyl group, arylsilyl group, amine group, acyl group, carbonyl group, carboxyl group, ester group, sulfinyl group, sulfonyl group, and phosphino group is not substituted with deuterium, halogen, unsubstituted 1 to 2 This means that the alkyl group may be substituted with one or more groups selected from an alkyl group having 0 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 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 aryl group having 6 to 30 carbon atoms, an unsubstituted heteroaryl group having 3 to 30 carbon atoms, an unsubstituted alkylsilyl group having 3 to 20 carbon atoms, an unsubstituted arylsilyl group having 6 to 20 carbon atoms, an unsubstituted amine 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 sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

[0050] 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, different modes of designating a substituent or attaching a fragment are considered equivalent.

[0051] In the compounds referred to herein, multiple substitution refers to the range up to the most available substitution, including double substitution.When a substituent in a compound referred to herein means multiple substitution (including double substitution, triple substitution, quadruple substitution, etc.), it means that the substituent may be present at multiple available substitution positions on its bond structure, and the substituents present at all multiple available substitution positions may be the same structure or different structures.

[0052] In the compounds referred to herein, unless specifically limited to the case where adjacent substituents may be bonded to form a ring, adjacent substituents in the compounds cannot be bonded to form a ring. In the compounds referred to herein, adjacent substituents may be bonded to form a ring, including the case where adjacent substituents are bonded to form a ring and the case 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 a monocyclic or polycyclic ring, and may be an alicyclic ring, a heteroalicyclic ring, an aryl ring, or a 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.

[0053] The statement that adjacent substituents may be bonded to form a ring is also recognized as meaning 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:

[0054] [ka]

[0055] 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:

[0056] [ka]

[0057] In addition, the statement that adjacent substituents may be bonded to form a ring is also recognized as meaning that when one of two substituents bonded to carbon atoms directly bonded to each other represents hydrogen, the second substituent is bonded to the position to which the hydrogen atom is bonded to form a ring. An example is shown in the following formula.

[0058] [ka]

[0059] According to one embodiment of the present invention, M(L a ) m (L b ) n (L c ) q Disclosed are metal complexes having the general formula: (L a , L b and L c are the first, second and third ligands, respectively, coordinated with a metal M, where the metal M is a metal having a relative atomic mass greater than 40; L a , Lb and L c may be linked to form a multidentate ligand; m is 1 or 2, n is 1 or 2, q is 0 or 1, and m+n+q is equal to the oxidation state of the metal M; If m is greater than 1, L a may be the same or different, and when n is greater than 1, L b may be the same or different, Said first ligand L a has a structure represented by formula 1, [ka] X1 to X4 are the same or different at each occurrence and are selected from CR1 or N; Y1 to Y4 are the same or different at each occurrence and are selected from CR2 or N; R1 and R2 may be the same or different at each occurrence and are selected from the group consisting of 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 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 aryloxy group having 6 to 3 ... 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 amine group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a nitrile group, an isonitrile group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; In formula 1, adjacent substituents may be bonded to form a ring, Said second ligand L b has a structure represented by formula 2, [ka] R t ~R z are the same or different at each occurrence and are selected from the group consisting of 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 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 is selected from the group consisting of unsubstituted 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 amine groups, acyl groups, carbonyl groups, carboxyl groups, ester groups, nitrile groups, isonitrile groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof, each of which has 0 to 20 carbon atoms; In formula 2, adjacent substituents may be bonded to form a ring, Said third ligand L c is a monoanionic bidentate ligand.

[0060] In these examples, the phrase "in Formula 1, adjacent substituents may be bonded to form a ring" may include a situation in which adjacent substituents R1, adjacent substituents R2, and / or adjacent substituents R1 and R2 are bonded to form a ring, as well as a situation in which adjacent substituents R1, adjacent substituents R2, and / or adjacent substituents R1 and R2 do not have to be bonded to form a ring.

[0061] In the examples, "in formula 2, adjacent substituents may be bonded to form a ring" means that adjacent substituents R x , R y , R z , R t , R u , R v and R ware bonded to each other to form a ring, for example, adjacent substituents R x and R y adjacent substituents R y and R z adjacent substituents R u and R v adjacent substituents R t and R z adjacent substituents R t and R u adjacent substituents R w and R v When one or more of the substituents R are bonded to each other to form a ring, and when the adjacent substituents R x , R y , R z , R t , R u , R v and R w They do not have to be bonded together to form a ring. For example, adjacent substituents R x and R y adjacent substituents R y and R z adjacent substituents R u and R v adjacent substituents R t and R z adjacent substituents R t and R u adjacent substituents R w and R v The present invention may also include a situation in which one or more of the groups do not necessarily bond to form a ring.

[0062] In the present invention, when a substituent is selected from hydrogen, said hydrogen refers to its isotope protium (H) and not the other isotopes deuterium or tritium.

[0063] According to one embodiment of the invention, the metal M is selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt.

[0064] According to one embodiment of the present invention, the metal M is selected from Pt or Ir.

[0065] According to one embodiment of the present invention, at least one of X1 to X4 is selected from CR1.

[0066] According to one embodiment of the present invention, at least one of X1 to X4 is selected from N.

[0067] According to an embodiment of the present invention, at least one of Y1 to Y4 is selected from N.

[0068] According to one embodiment of the present invention, X1 to X4 are identical or different at each occurrence and are selected from CR1.

[0069] According to one embodiment of the present invention, X1 and / or X3 at each occurrence may be the same or different and are selected from CR1, and R1 at each occurrence may be the same or different and are selected from 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 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 selected from the group consisting of substituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted 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 amine groups, acyl groups, carbonyl groups, carboxyl groups, ester groups, nitrile groups, isonitrile groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof, Among them, adjacent substituents R1 may be bonded to form a ring.

[0070] According to one embodiment of the present invention, X1 and X3, each occurrence, may be the same or different and are selected from CR1, and R1, each occurrence, may be the same or different and are selected from the group consisting of 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 aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms.

[0071] According to one embodiment of the present invention, X1 and X3, each occurrence, are the same or different and selected from CR1, and R1, each occurrence, are the same or different and selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, and X2 and X4 are CH.

[0072] According to one embodiment of the present invention, X1 and X4 are CH, and X2 and X3, identical or different at each occurrence, are selected from CR1.

[0073] According to one embodiment of the present invention, R1, at each occurrence, is selected from the group consisting of hydrogen, deuterium, fluorine, methyl, ethyl, 2-butyl, isopropyl, tert-butyl, isobutyl, cyclopentyl, cyclohexyl, deuterated methyl, deuterated propyl, isopropylamino, phenyl, 2,6-dimethylphenyl, pyridyl, vinyl, and combinations thereof; Among them, adjacent substituents R1 may be bonded to form a ring.

[0074] According to one embodiment of the present invention, Y1 to Y4 at each occurrence may be the same or different and are selected from CR2, and R2 at each occurrence may be the same or different and are selected from hydrogen, 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 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 selected from the group consisting of alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted 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 amine groups, acyl groups, carbonyl groups, carboxyl groups, ester groups, nitrile groups, isonitrile groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof, Among them, adjacent substituents R2 may be bonded to form a ring.

[0075] According to one embodiment of the present invention, Y2 is CR2, and R2, each occurrence of which may be the same or different, is selected from the group consisting of halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, alkoxy group having 1 to 20 carbon atoms, aryloxy group having 6 to 30 carbon atoms, alkenyl group having 2 to 20 carbon atoms, substituted or unsubstituted aryl group, Selected from the group consisting of an aryl group having 6 to 30 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 amine group, acyl group, carbonyl group, carboxyl group, ester group, nitrile group, isonitrile group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof, wherein adjacent substituents R2 may be bonded to form a ring.

[0076] According to one embodiment of the present invention, Y2 is CR2, and R2, each occurrence, may be the same or different and 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, and a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, wherein adjacent substituents R2 may be bonded to form a ring.

[0077] According to one embodiment of the present invention, R2 is an alkyl group having 1 to 20 carbon atoms.

[0078] According to one embodiment of the present invention, Y2 is CR2, and R2, which may be the same or different at each occurrence, is selected from a substituted or unsubstituted alkyl or cycloalkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms; Y1, Y3, and Y4 are all CH; Among them, adjacent substituents R2 may be bonded to form a ring.

[0079] According to one embodiment of the present invention, R2, each occurrence being the same or different, is selected from the group consisting of hydrogen, fluorine, methyl, ethyl, isopropyl, 2-butyl, isobutyl, tert-butyl, pentyl-3-yl, cyclopentyl, cyclohexyl, 4,4-dimethylcyclohexyl, neopentyl, 2,4-dimethylpentan-3-yl, 1,1-dimethylsilacyclohexan-4-yl, cyclopentylmethyl, cyano, trifluoromethyl, trimethylsilyl, phenyldimethylsilyl, bicyclo[2,2,1]heptan-2-yl, adamantyl, deuterated isopropyl, phenyl or pyridyl, and combinations thereof.

[0080] According to one embodiment of the present invention, the first ligand L a may be the same or different for each occurrence of L a1 ~L a1101 Any one or two selected from the group consisting of: a1 ~L a1101 For the specific structure, please refer to claim 10.

[0081] According to one embodiment of the present invention, the first ligand L a may be the same or different for each occurrence of L a1 ~L a1189 Any one or two selected from the group consisting of: a1 ~L a1189 For the specific structure, please refer to claim 10.

[0082] According to one embodiment of the present invention, in the formula 2, R t ~R zand each occurrence may be the same or different and are selected from the group consisting of 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, and combinations thereof.

[0083] According to one embodiment of the present invention, in the formula 2, R t is selected from hydrogen, deuterium, or a methyl group, and R u ~R z is the same or different at each occurrence and is selected from hydrogen, deuterium, fluorine, methyl, ethyl, propyl, cyclobutyl, cyclopentyl, cyclohexyl, 3-methylbutyl, 3-ethylpentyl, trifluoromethyl, and combinations thereof.

[0084] According to one embodiment of the present invention, the second ligand L b The structure of each occurrence may be the same or different. b1 ~L b383 Any one or two selected from the group consisting of: b1 ~L b383 For the specific structure, please refer to claim 12.

[0085] According to one embodiment of the present invention, the first ligand L a and / or a second ligand L b The hydrogen atoms in may be partially or completely deuterated.

[0086] According to one embodiment of the present invention, the third ligand L c The structure of [ka] It is one of the following selected types. (R a , R b and R c may represent mono-, multiply- or no substitution; X b are O, S, Se, NR, or the same or different for each occurrence. N1 and CR C1 RC2 selected from the group consisting of X c and X d are O, S, Se and NR, which may be the same or different for each occurrence. N2 selected from the group consisting of R a , R b , R c , R N1 , R N2 , R C1 and R C2 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 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 selected from the group consisting of unsubstituted 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 amine groups, acyl groups, carbonyl groups, carboxyl groups, ester groups, nitrile groups, isonitrile groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof, L c In the structure of the formula (I), adjacent substituents may be bonded to form a ring.

[0087] In this embodiment, adjacent substituents may be bonded to form a ring, which means that adjacent groups of substituents, for example, two substituents R a two substituents R b two substituents R c R a and R b R a and R c R b and Rc 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 R a and R N2 R b and R N2 R C1 and R C2 This means that any one or more of these substituents may be bonded to each other to form a ring. Obviously, these substituents do not have to be bonded to each other to form a ring.

[0088] According to one embodiment of the present invention, the third ligand L c may be the same or different for each occurrence of L c1 ~L c227 L c1 ~L c227 For the specific structure, please refer to claim 15.

[0089] According to one embodiment of the present invention, the metal complex is Ir(L a )2(L b ) or Ir(L a )(L b )(L c ) and the metal complex is Ir(L a )2(L b ), when the first ligand L a may be the same or different for each occurrence of L a1 ~L a1189 and the second ligand L b may be the same or different for each occurrence of L b1 ~L b383 The metal complex is any one selected from the group consisting of Ir(La )(L b )(L c ), when the first ligand L a may be the same or different for each occurrence of L a1 ~L a1189 and the second ligand L b may be the same or different for each occurrence of L b1 ~L b383 and the third ligand L is any one selected from the group consisting of c may be the same or different for each occurrence of L c1 ~L c227 It is any one selected from the group consisting of:

[0090] According to one embodiment of the present invention, the metal complex is a complex selected from the specific structures shown in claim 16.

[0091] According to another embodiment of the present invention, there is further disclosed an electroluminescent device including an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer includes the metal complex described in any one of the above embodiments.

[0092] According to one embodiment of the present invention, the electroluminescent element emits red or white light.

[0093] According to one embodiment of the present invention, the organic layer is a light-emitting layer and the metal complex is a light-emitting material.

[0094] According to an embodiment of the present invention, the organic layer further comprises a host material.

[0095] According to one embodiment of the present invention, the host material comprises at least one chemical group selected from the group consisting of benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazolyl, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorenyl, silicon fluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

[0096] According to another embodiment of the present invention, there is further disclosed a combination of compounds comprising a metal complex as described in any one of the above embodiments.

[0097] Combination with other materials

[0098] 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.

[0099] 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.

[0100] 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 workstation, 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. [Example]

[0101] Examples of material synthesis

[0102] The method for preparing the metal complex according to the present invention is not limited. Taking the following compounds as typical but non-limiting examples, the synthesis route and preparation method thereof are as follows:

[0103] Synthesis Example 1: Compound Ir(L a126 )2(L b361 ) synthesis

[0104] Step 1: Synthesis of iridium dimer [ka] To a 100 mL round-bottom flask were added Intermediate 1 (4.06 g, 14.64 mmol), iridium trichloride trihydrate (1.29 g, 3.66 mmol), ethoxyethanol (39 mL), and water (13 mL). Nitrogen gas was bubbled through the reaction mixture for 3 minutes. The reaction mixture was then heated under nitrogen gas at reflux for 24 hours until the color of the reaction solution changed from yellow-green to deep red. The reaction mixture was then cooled to room temperature and filtered. The solid was washed multiple times with methanol and then dried to obtain the dimer.

[0105] Step 2: Compound Ir(L a126 )2(L b361 ) synthesis [ka] A mixture of the iridium dimer obtained in Step 1 (1.33 g, 0.85 mmol), 3,7-diethyl-1,1,1-trifluorononane-4,6-dione (679 mg, 2.55 mmol), potassium carbonate (1.17 g, 8.5 mmol), and 2-ethoxyethanol (28 mL) was stirred at room temperature for 24 hours under nitrogen gas protection. After TLC showed the reaction was complete, Celite was added to the funnel and the reaction mixture was filtered. The filter cake was washed several times with ethanol, and the product on the filter cake was rinsed into solution with dichloromethane. Next, a certain amount of ethanol was added to the solution, and the dichloromethane in the solution was carefully removed by rotation in an evaporator. A red solid precipitated from the solution and filtered. The solid obtained was washed several times with ethanol and pumped to dryness, after which the red solid product Ir(L a126 )2(L b361 ) (1.29 g, 75% yield) was obtained. The obtained product was confirmed to be the target product with a molecular weight of 1010.

[0106] Synthesis Example 2: Compound Ir(L a577 )2(L b378 ) synthesis

[0107] Step 1: Synthesis of iridium dimer [ka] To a 100 mL round-bottom flask were added Intermediate 2 (3.34 g, 10.53 mmol), iridium trichloride trihydrate (1.24 g, 3.51 mmol), ethoxyethanol (39 mL), and water (13 mL). Nitrogen gas was bubbled through the reaction mixture for 3 minutes. The reaction mixture was then heated under nitrogen gas at reflux for 24 hours until the color of the reaction solution changed from yellow-green to deep red. The reaction mixture was then cooled to room temperature and filtered. The solid was washed multiple times with methanol and then dried to give the iridium dimer (2.65 g, 87.8% yield).

[0108] Step 2: Compound Ir(L a577 )2(L b378) synthesis [ka] A mixture of the iridium dimer obtained in Step 1 (1.33 g, 0.77 mmol), 3,7-diethyl-9,9-difluoro-decane-4,6-dione (808 mg, 3.1 mmol), potassium carbonate (1.06 g, 7.71 mmol), and 2-ethoxyethanol (22 mL) was stirred at room temperature for 24 hours under nitrogen gas protection. After TLC showed the reaction was complete, Celite was added to the funnel and the reaction mixture was filtered. The filter cake was washed several times with ethanol, and the product on the filter cake was rinsed into solution with dichloromethane. Next, a certain amount of ethanol was added to the solution, and the dichloromethane in the solution was carefully removed by rotating it in an evaporator. A red solid precipitated from the solution and was filtered. The solid obtained was washed several times with ethanol and pumped to dryness, after which the red solid product, compound Ir(L), was obtained. a577 )2(L b378 ) (1.4 g, yield 83.5%) was obtained. The obtained product was confirmed to be the target product with a molecular weight of 1087.

[0109] Synthesis Example 3: Compound Ir(L a577 )2(L b361 ) synthesis [ka] A mixture of iridium dimer (1.33 g, 0.77 mmol), 3,7-diethyl-1,1,1-trifluorononane-4,6-dione (820 mg, 3.1 mmol), potassium carbonate (1.06 g, 7.71 mmol), and 2-ethoxyethanol (22 mL) was stirred under nitrogen gas protection at room temperature for 24 hours. After TLC showed the reaction was complete, Celite was added to the funnel and the reaction mixture was filtered. The filter cake was washed several times with ethanol, and the product on the filter cake was rinsed into solution with dichloromethane. Next, a certain amount of ethanol was added to the solution, and the dichloromethane in the solution was carefully removed by rotating it in an evaporator. A red solid precipitated from the solution and was filtered. The solid obtained was washed several times with ethanol and pumped to dryness, after which the red solid product, compound Ir(L), was obtained. a577 )2(L b361 ) (1.4 g, yield 83.4%) was obtained. The obtained product was confirmed to be the target product with a molecular weight of 1091.

[0110] Synthesis Example 4: Compound Ir(L a331 )2(L b378 ) synthesis [ka] A mixture of iridium dimer (1.2 g, 0.72 mmol), 3,7-diethyl-9,9-difluoro-decane-4,6-dione (755 mg, 2.88 mmol), potassium carbonate (995 mg, 7.2 mmol), and 2-ethoxyethanol (24 mL) was stirred under nitrogen gas protection at room temperature for 24 hours. After TLC showed the reaction was complete, Celite was added to the funnel and the reaction mixture was filtered. The filter cake was washed several times with ethanol, and the product on the filter cake was rinsed into solution with dichloromethane. Next, a certain amount of ethanol was added to the solution, and the dichloromethane in the solution was carefully removed by rotating it in an evaporator. A red solid precipitated from the solution and filtered. The solid obtained was washed several times with ethanol and pumped to dryness, after which the red solid product, compound Ir(L), was obtained. a331 )2(L b378) (1.4 g, 92% yield) was obtained. The obtained product was confirmed to be the target product with a molecular weight of 1059.

[0111] Synthesis Example 5: Compound Ir(L a331 )2(L b361 ) synthesis [ka] A mixture of iridium dimer (1.24 g, 0.745 mmol), 3,7-diethyl-1,1,1-trifluorononane-4,6-dione (793 mg, 2.98 mmol), potassium carbonate (1.03 g, 7.45 mmol), and 2-ethoxyethanol (25 mL) was stirred under nitrogen gas protection at room temperature for 24 hours. After TLC showed the reaction was complete, Celite was added to the funnel and the reaction mixture was filtered. The filter cake was washed several times with ethanol, and the product on the filter cake was rinsed into solution with dichloromethane. Next, a certain amount of ethanol was added to the solution, and the dichloromethane in the solution was carefully removed by rotating it in an evaporator. A red solid precipitated from the solution and was filtered. The solid obtained was washed several times with ethanol and pumped to dryness, after which the red solid product, compound Ir(L), was obtained. a331 )2(L b361 ) (1.29 g, 82% yield) was obtained. The obtained product was confirmed to be the target product with a molecular weight of 1062.

[0112] Synthesis Example 6: Compound Ir(L a577 )2(L b31 ) synthesis [ka] A mixture of iridium dimer (1.25 g, 0.8 mmol), 3,7-diethylnonane-4,6-dione (650 mg, 3.2 mmol), potassium carbonate (1.11 g, 8 mmol), and 2-ethoxyethanol (25 mL) was stirred under nitrogen gas protection at room temperature for 24 hours. After TLC showed the reaction was complete, Celite was added to the funnel and the reaction mixture was filtered. The filter cake was washed several times with ethanol, and the product on the filter cake was rinsed into solution with dichloromethane. Next, a certain amount of ethanol was added to the solution, and the dichloromethane in the solution was carefully removed by rotating it in an evaporator. A red solid precipitated from the solution and was filtered. The solid obtained was washed several times with ethanol and pumped to dryness, after which the red solid product, compound Ir(L), was obtained. a577 )2(L b31 ) (1.09 g, 66% yield) was obtained. The obtained product was confirmed to be the target product with a molecular weight of 1037.

[0113] Synthesis Example 7: Compound Ir(L a577 )2(L b116 ) synthesis [ka] A mixture of iridium dimer (1.2 g, 0.8 mmol), 3,3,7-triethylnonane-4,6-dione (500 mg, 2.4 mmol), potassium carbonate (1.11 g, 8 mmol), and 2-ethoxyethanol (25 mL) was stirred at room temperature under nitrogen gas protection for 24 hours. After TLC showed the reaction was complete, Celite was added to the funnel and the reaction mixture was filtered. The filter cake was washed several times with ethanol, and the product on the filter cake was rinsed into solution with dichloromethane. Next, a certain amount of ethanol was added to the solution, and the dichloromethane in the solution was carefully removed by rotating it in an evaporator. A red solid precipitated from the solution and was filtered. The solid obtained was washed several times with ethanol and pumped to dryness, after which the red solid product, compound Ir(L), was obtained. a577 )2(L b116) (1.1 g, 65% yield) was obtained. The obtained product was confirmed to be the target product with a molecular weight of 1065.

[0114] Synthesis Example 8: Compound Ir(L a331 )2(L b116 ) synthesis [ka] A mixture of iridium dimer (1.25 g, 0.75 mmol), 3,3,7-triethylnonane-4,6-dione (540 mg, 2.25 mmol), potassium carbonate (1.04 g, 7.5 mmol), and 2-ethoxyethanol (22 mL) was stirred under nitrogen gas protection at room temperature for 24 hours. After TLC showed the reaction was complete, Celite was added to the funnel and the reaction mixture was filtered. The filter cake was washed several times with ethanol, and the product on the filter cake was rinsed into solution with dichloromethane. Next, a certain amount of ethanol was added to the solution, and the dichloromethane in the solution was carefully removed by rotating it in an evaporator. A red solid precipitated from the solution and was filtered. The solid obtained was washed several times with ethanol and pumped to dryness, after which the red solid product, compound Ir(L), was obtained. a331 )2(L b116 ) (1.25 g, 83% yield) was obtained. The product obtained was confirmed to be the target product with a molecular weight of 1037.

[0115] Synthesis Example 9: Compound Ir(L a331 )(L b361 )(L c161 ) synthesis [ka] A mixture of iridium dimer (0.9 g, 0.5 mmol), 3,7-diethyl-1,1,1-trifluorononane-4,6-dione (0.5 g, 2 mmol), potassium carbonate (1 g, 5.3 mmol), and 2-ethoxyethanol (12 mL) was stirred at room temperature under nitrogen gas protection for 24 hours. After TLC showed the reaction was complete, Celite was added to the funnel and the reaction mixture was filtered. The filter cake was washed several times with ethanol, and the product on the filter cake was rinsed into solution with dichloromethane. Next, a certain amount of ethanol was added to the solution, and the dichloromethane in the solution was carefully removed by rotating it in an evaporator. A red solid precipitated from the solution and was filtered. The solid obtained was washed several times with ethanol and pumped to dryness, after which the red solid product, compound Ir(L), was obtained. a331 )(L b361 )(L c161 ) (0.82 g, 75% yield) was obtained. The product obtained was confirmed to be the target product with a molecular weight of 1061.

[0116] Synthesis Example 10: Compound Ir(L a126 )(L b361 )(L c141 ) synthesis [ka] A mixture of iridium dimer (1.14 g, 0.7 mmol), 3,7-diethyl-1,1,1-trifluorononane-4,6-dione (0.5 g, 2 mmol), potassium carbonate (1 g, 5.3 mmol), and 2-ethoxyethanol (12 mL) was stirred at room temperature under nitrogen gas protection for 24 hours. After TLC showed the reaction was complete, Celite was added to the funnel and the reaction mixture was filtered. The filter cake was washed several times with ethanol, and the product on the filter cake was rinsed into solution with dichloromethane. Next, a certain amount of ethanol was added to the solution, and the dichloromethane in the solution was carefully removed by rotating it in an evaporator. A red solid precipitated from the solution and was filtered. The solid obtained was washed several times with ethanol and pumped to dryness, after which the red solid product, compound Ir(L), was obtained. a126 )(Lb361 )(L c141 ) (1.1 g, 79% yield) was obtained. The obtained product was confirmed to be the target product with a molecular weight of 1009.

[0117] Those skilled in the art should know that the above preparation methods are merely exemplary and can be modified to obtain the structures of other compounds of the present invention.

[0118] Element Example 1

[0119] First, a glass substrate with a 120 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 attached to a substrate holder and placed in a vacuum chamber. Hereinafter, for the specified organic layers, a vacuum of approximately 10°C was used. -8 In the case of the ITO anode, the layers were sequentially deposited by hot vacuum evaporation at a rate of 0.2-2 Å / s. Compound HI was used as the hole injection layer (HIL), compound HT was used as the hole transport layer (HTL), and compound EB was used as the electron blocking layer (EBL). Then, compound Ir(L) of the present invention was deposited. a126 )2(L b361 The host compound RH was doped with 3% ZnO as the light-emitting layer (EML). The compound HB was used as the hole-blocking layer (HBL). The compound ET and 8-hydroxyquinoline-lithium (Liq) were evaporated on the HBL as the electron-transporting layer (ETL). Finally, a 1-nm-thick Liq was evaporated as the electron-injection layer, and a 120-nm-thick Al was evaporated as the cathode. The device was then transferred to a glove box and encapsulated with a glass cover and a moisture absorbent to complete the device.

[0120] Comparative Example 1 of the Element

[0121] The method for preparing Comparative Example 1 of the device was to use the comparative compound RD1 and the compound Ir(L) of the present invention in the light-emitting layer (EML). a126 )2(L b361) is replaced, the element is the same as Example 1.

[0122] Comparative example 2 of the element

[0123] The method for preparing the device of Comparative Example 2 was to use the comparative compound RD2 and the compound Ir(L) according to the present invention in the light-emitting layer (EML). a126 )2(L b361 ) is replaced, the element is the same as Example 1.

[0124] Element Example 2

[0125] The preparation method of Example 2 of the device was carried out by using the compound Ir(L) of the present invention in the light-emitting layer (EML). a331 )2(L b361 ) and the compound Ir(L a126 )2(L b361 ) (compound Ir(L a331 )2(L b361 The device is the same as in Example 1, except that the weight ratio of compound RH to compound EB is 5:95, and compound EB1 is used in the EBL.

[0126] Element Example 3

[0127] The preparation method of Example 3 of the device was carried out by using the compound Ir(L) of the present invention in the light-emitting layer (EML). a331 )2(L b378 ) and the compound Ir(L a331 )2(L b361 ) is replaced, the element is the same as Example 2.

[0128] Element Example 4

[0129] The preparation method of Example 4 of the device was carried out by using the compound Ir(L) of the present invention in the light-emitting layer (EML). a577 )2(L b378 ) and the compound Ir(L a331 )2(L b361 ) is replaced, the element is the same as Example 2.

[0130] Element Example 5

[0131] The preparation method of Example 5 of the device was carried out by using the compound Ir (L a577 )2(L b361 ) and the compound Ir(L a331 )2(L b361 ) is replaced, the element is the same as Example 2.

[0132] Comparative Example 3 of the Element

[0133] The method for preparing the device of Comparative Example 3 was to use the comparative compound RD3 and the compound Ir(L) according to the present invention in the light-emitting layer (EML). a331 )2(L b361 ) is replaced, the element is the same as Example 2.

[0134] Comparative Example 4 of the Element

[0135] The method for preparing the device of Comparative Example 4 was to use the comparative compound RD4 and the compound Ir(L) according to the present invention in the light-emitting layer (EML). a331 )2(L b361 ) is replaced, the element is the same as Example 2.

[0136] Comparative Example 5 of the Element

[0137] The method for preparing the device of Comparative Example 5 was to use the comparative compound RD5 and the compound Ir(L) according to the present invention in the light-emitting layer (EML). a331 )2(L b361 ) is replaced, the element is the same as Example 2.

[0138] The detailed layer structure and thickness of the element are shown in the table below: Layers made of two or more materials are obtained by doping different compounds in the weight ratios described above.

[0139] [Table 1]

[0140] The structure of the material used in the element is represented as follows: [ka] TIFF0007774835000039.tif80168

[0141] Table 2 shows the color coordinates (CIE), emission wavelength (λmax) and luminance at 15 mA / cm for Device Example 1, Comparative Examples 1-2, Device Examples 2-5 and Comparative Examples 3-5 measured at a luminance of 1000 nits. 2 The external quantum efficiency (EQE) data at a constant current density of 80 mA / cm is shown. 2 The useful life of the element, LT97, was measured.

[0142] [Table 2]

[0143] summary As can be seen from the data shown in Table 2, the color coordinates and emission wavelengths were comparable between Example 1 and Comparative Examples 1 and 2. However, the most important point is as follows: compared with Comparative Example 1, Example 1 had an 8.2% increase in service life and a 4.0% increase in external quantum efficiency. compared with Comparative Example 2, Example 1 had a 23.3% increase in service life and a 4.7% increase in external quantum efficiency. As a result, by substituting two deuterium atoms at the 3- and 4-positions of the isoquinoline ligand, both service life and efficiency can be improved simultaneously, with the service life being significantly improved in particular, proving the uniqueness and importance of this structural feature.

[0144] As can be seen from a comparison between Example 2 and Comparative Examples 3-5, the color coordinates and emission wavelengths in Example 2 and Comparative Examples 3-5 were comparable. However, the most important findings are as follows: Compared to Comparative Example 3, Example 2 saw a 23% increase in service life and a 2.4% increase in external quantum efficiency. Compared to Comparative Example 4, Example 2 saw an 8.5% increase in service life and a 2.2% increase in external quantum efficiency. Compared to Comparative Example 5, Example 2 saw an 18.5% increase in service life and a slight increase in external quantum efficiency. At the same time, the data for Examples 3-5 showed similar long service life and high efficiency characteristics to Example 2. As can be seen from the data for these devices, the substitution of two deuterium atoms at the 3- and 4-positions of the isoquinoline ligand simultaneously improved both service life and efficiency, with a particularly significant improvement in service life, once again demonstrating the uniqueness and importance of this structural feature.

[0145] 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. Ir(L ａ ) 2 (L ｂ ) a metal complex having the general formula: (L ａ , Lb are a first ligand and a second ligand coordinated to the metal Ir, respectively; L ａ , Lb may be linked to form a multidentate ligand; L ａ may be the same or different, The first ligand L ａ has a structure represented by Formula 1, 【Chemistry 1】 X １ ~X ４ is the same or different for each occurrence １ Selected from Y １ ~Y ４ is the same or different for each occurrence ２ Selected from R １ are the same or different at each occurrence and are selected from the group consisting of hydrogen, 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, and a nitrile group; R ２ are the same or different at each occurrence and are selected from the group consisting of hydrogen, 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, and a nitrile group; Said second ligand L ｂ has a structure represented by formula 2: 【Chemistry 2】 R ｔ ~R ｚ are the same or different at each occurrence and are selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, and substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms; The substituents of the substituted alkyl group, substituted cycloalkyl group, substituted aryl group, substituted heteroaryl group, substituted alkylsilyl group, and substituted arylsilyl group are one or more selected from 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 alkoxy group having 1 to 20 carbon atoms, an unsubstituted aryloxy group having 6 to 30 carbon atoms, an unsubstituted aryl group having 6 to 30 carbon atoms, an unsubstituted heteroaryl group having 3 to 30 carbon atoms, an unsubstituted alkylsilyl group having 3 to 20 carbon atoms, an unsubstituted arylsilyl group having 6 to 20 carbon atoms, an unsubstituted amine group having 0 to 20 carbon atoms, a nitrile group, and sulfanyl.

2. X １ and / or X ３ is the same or different for each occurrence １ and R １ are the same or different at each occurrence and are selected from the group consisting of hydrogen, 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, and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; The metal complex of claim 1.

3. X １ and X ３ is the same or different for each occurrence １ and R １ are the same or different at each occurrence and are selected from the group consisting of hydrogen, 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, and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; The metal complex of claim 1.

4. X １ and X ３ is the same or different for each occurrence １ and R １ are the same or different at each occurrence and are selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms; X ２ and X ４ is CH, The metal complex of claim 1.

5. X １ and X ４ is CH, and X ２ and X ３ is the same or different for each occurrence １ The metal complex according to claim 1, selected from:

6. R １ each occurrence may be the same or different and is selected from the group consisting of hydrogen, fluorine, methyl, ethyl, 2-butyl, isopropyl, tert-butyl, isobutyl, cyclopentyl, cyclohexyl, deuterated methyl, deuterated propyl, phenyl, 2,6-dimethylphenyl, and pyridyl; The metal complex according to any one of claims 1 to 5.

7. Y １ ~Y ４ is the same or different for each occurrence ２ and R ２ are the same or different at each occurrence and are selected from the group consisting of hydrogen, 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, and a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms; The metal complex according to any one of claims 1 to 6.

8. Y ２ is CR ２ and R ２ are the same or different at each occurrence and are 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, and a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms; The metal complex according to any one of claims 1 to 6.

9. Y ２ is CR ２ and R ２ are the same or different at each occurrence and are 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, and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; The metal complex according to claim 8.

10. Y ２ is CR ２ and R ２ each occurrence may be the same or different and selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms; Y １ , Y ３ and Y ４ are both CH, The metal complex according to claim 9.

11. R ２ and each occurrence may be the same or different and are selected from the group consisting of hydrogen, fluorine, a methyl group, an ethyl group, an isopropyl group, a 2-butyl group, an isobutyl group, a tert-butyl group, a pentyl-3-yl group, a cyclopentyl group, a cyclohexyl group, a 4,4-dimethylcyclohexyl group, a neopentyl group, a 2,4-dimethylpentan-3-yl group, a 1,1-dimethylsilacyclohexan-4-yl group, a cyclopentylmethyl group, a cyano group, a trifluoromethyl group, a trimethylsilyl group, a phenyldimethylsilyl group, a bicyclo[2,2,1]heptan-2-yl group, an adamantyl group, a deuterated isopropyl group, a phenyl group, and a pyridyl group.

12. First ligand L ａ The metal complex according to claim 1, wherein each occurrence of is the same or different and is any one or any two selected from the group consisting of the following structures: 【Transformation 3】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】

13. In the formula 2, R ｔ ~R ｚ and each occurrence may be the same or different and are selected from the group consisting of hydrogen, deuterium, halogen, and a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

14. Second ligand L ｂ The structure of each occurrence may be the same or different, 【Chemistry 4】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 The metal complex according to any one of claims 1 to 13, selected from the group consisting of:

15. Second ligand L ｂ The metal complex according to claim 14, wherein the hydrogen atoms in the formula (I) may be partially or completely deuterated.

16. The metal complex is 【Transformation 5】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 Selected from the group consisting of: The metal complex of claim 14.

17. an anode; A cathode; an organic layer disposed between the anode and the cathode, An electroluminescent device, wherein the organic layer comprises a metal complex according to any one of claims 1 to 16.

18. 18. The electroluminescent device of claim 17, wherein the electroluminescent device emits red or white light.

19. 18. The electroluminescent device according to claim 17, wherein the organic layer is an emissive layer and the metal complex is an emissive material.

20. 20. The electroluminescent device of claim 19, wherein the organic layer further comprises a host material.

21. 21. The electroluminescent device of claim 20, wherein the host material comprises at least one chemical group selected from the group consisting of benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazolyl, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorenyl, silicon fluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

22. A composition of compounds comprising the metal complex of any one of claims 1 to 16.

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