Light emitting materials with polycyclic ligands

Abstract

To provide a series of novel metal complexes having a polycyclic ligand. To provide a novel metal complex capable of better adjusting the emission color of a device while maintaining a very narrow full width at half maximum, reducing the driving voltage of the device or maintaining a low voltage level, improving the efficiency of the device, and greatly improving the service life of the device. To provide a novel metal complex that provides better device performance.SOLUTION: A metal complex, comprising a ligand La having a structure represented by formula 1: Wherein ring A and ring B are each independently selected from a 5-membered unsaturated carbocyclic ring, an aromatic ring having 6 to 30 carbon atoms or a heteroaromatic ring having 3 to 30 carbon atoms; ) 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 more particularly to metal complexes having polycyclic ligands, and electroluminescent devices and compound combinations containing the metal complexes. [Background technology]

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

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

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

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

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

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

[0008] Phosphorescent metal complexes have been applied in organic electroluminescent lighting or display fields as phosphorescent doping materials in the light-emitting layer.

[0009] In CN110698518A, [ka] Disclosed are metal complexes having the structure: where X is N or P. One of the many structures disclosed is: [ka] The present inventors have investigated the improvement of material performance by bridging N and P atoms, but have not focused on the improvement of performance by introducing a fused ring system into a specific position in a specific ring.

[0010] In CN110790797A, [ka] One of the many structures disclosed is: [ka] The present inventors have investigated the improvement of material performance by bridging O and S atoms, but have not focused on the improvement of performance by introducing a fused ring system at a specific position in a specific ring. [Prior art documents] [Patent documents]

[0011] [Patent Document 1] Chinese Patent Application Publication No. 110698518 [Patent Document 2] Chinese Patent Application Publication No. 110790797 [Non-patent literature]

[0012] [Non-Patent Document 1] Applied Physics Letters, 1987, 5 1(12):913~915 DISCLOSURE OF THE INVENTION [Problem to be solved by the invention]

[0013] Currently, there are still many shortcomings in the performance of developed metal complexes in electroluminescent devices. To meet the ever-increasing needs of the industry, such as lower voltage, higher device efficiency, luminescent color in a specific wavelength range, more saturated luminescent color, and longer device service life, there is still an urgent need for in-depth research and development of related metal complexes.

[0014] (Summary of the Invention) The present invention aims to solve at least some of the problems described above by providing a series of metal complexes having polycyclic ligands. These metal complexes can be used as emitting materials in organic electroluminescent devices. These novel metal complexes can better control the emission color of devices while maintaining a very narrow full width at half maximum, reduce the device's driving voltage or maintain a low voltage level, improve device efficiency, and significantly extend the device's service life. These novel metal complexes can provide better device performance.

[0015] According to one embodiment of the present invention, a ligand L having a structure represented by Formula 1 a A metal complex comprising: [ka] (Ring A and Ring B are each independently selected from a 5-membered unsaturated carbocyclic ring, an aromatic ring having 6 to 30 carbon atoms, or a heteroaromatic ring having 3 to 30 carbon atoms; R i are the same or different and represent mono-, multi- or no substitutions at each occurrence, and R ii are the same or different at each occurrence and represent mono-, multi- or no substitution; Y is SiR y R y , GeR y R y , N.R. y , PR y , O, S or Se; The Two R's y When two R y may be the same or different, X1~X2 are the same or different for each occurrence. x or selected from N, R, R i , R ii , R x and R yare 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 unsubstituted 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 cyano group, an isocyano group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituents R i , R x , R y , R and R ii may be bonded to form a ring, The metal is selected from metals with a relative atomic mass greater than 40.

[0016] According to another embodiment of the present invention, there is further disclosed an electroluminescent device, comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a ligand L having a structure represented by Formula 1: a The present invention also includes metal complexes comprising: [ka] (Ring A and Ring B are each independently selected from a 5-membered unsaturated carbocyclic ring, an aromatic ring having 6 to 30 carbon atoms, or a heteroaromatic ring having 3 to 30 carbon atoms; R i are the same or different and represent mono-, multi- or no substitutions at each occurrence, and R ii are the same or different at each occurrence and represent mono-, multi- or no substitution; Y is SiRy R y , GeR y R y , N.R. y , PR y , O, S or Se; The Two R's y When two R y may be the same or different, X1~X2 are the same or different for each occurrence. x or selected from N, R, R i , R ii , R x and R y 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 unsubstituted 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 cyano group, an isocyano group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituents R i , R x , R y , R and R ii may be bonded to form a ring, The metal is selected from metals with a relative atomic mass greater than 40.

[0017] According to other embodiments of the present invention, combinations of compounds containing the metal complexes described in the preceding embodiments are disclosed.

[0018] The novel metal complexes having polycyclic ligands according to the present invention can be used as luminescent materials in electroluminescent devices. These novel metal complexes can better adjust the emission color of the device while maintaining a very narrow full width at half maximum, reduce the driving voltage of the device or maintain a low voltage level, improve the efficiency of the device, and significantly improve the service life of the device. These novel metal complexes can provide better device performance. [Brief explanation of the drawings]

[0019] [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. [Figure 3] FIG. 1 shows structural formula 1 of the ligand La of the metal complexes disclosed herein. DETAILED DESCRIPTION OF THE INVENTION

[0020] 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.

[0021] 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.

[0022] 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.

[0023] 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.

[0024] 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.

[0025] 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.

[0026] The materials and structures described herein may also be used in the other organic electronic devices listed above.

[0027] "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.

[0028] "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.

[0029] 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.

[0030] 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).

[0031] 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.

[0032] 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).

[0033] Definitions of Substituent Terminology

[0034] Halogen or halide, as used herein, includes fluorine, chloro, bromine and iodine.

[0035] The alkyl group includes straight-chain and branched-chain alkyl groups. The alkyl group may be an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 12 carbon atoms, and more preferably an alkyl group having 1 to 6 carbon atoms. 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. Of these, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl and neopentyl are preferred.

[0036] 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.

[0037] 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.

[0038] 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.

[0039] 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.

[0040] 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.

[0041] 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.

[0042] 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.

[0043] 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.

[0044] 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.

[0045] 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.

[0046] 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 a group containing 1 to 20 unsubstituted hydrogen atoms, such as deuterium, halogen, or the like. This means that the alkyl group may be substituted with one or more selected from the group consisting of an alkyl group having from 3 to 20 ring carbon atoms, an unsubstituted cycloalkyl group having from 3 to 20 ring carbon atoms, an unsubstituted heteroalkyl group having from 1 to 20 carbon atoms, an unsubstituted aralkyl group having from 7 to 30 carbon atoms, an unsubstituted alkoxy group having from 1 to 20 carbon atoms, an unsubstituted aryloxy group having from 6 to 30 carbon atoms, an unsubstituted alkenyl group having from 2 to 20 carbon atoms, an unsubstituted aryl group having from 6 to 30 carbon atoms, an unsubstituted heteroaryl group having from 3 to 30 carbon atoms, an unsubstituted alkylsilyl group having from 3 to 20 carbon atoms, an unsubstituted arylsilyl group having from 6 to 20 carbon atoms, an unsubstituted amine group having from 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

[0047] When describing a molecular fragment as being attached to another moiety by a substituent or otherwise, it should be understood that the designation can be defined as either the fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or the entire molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, the designations of the substituents or different modes of attachment of the fragment are considered equivalent.

[0048] In the compounds described herein, hydrogen atoms may be partially or completely replaced with deuterium.Other atoms, such as carbon and nitrogen, may also be replaced with other stable isotopes thereof.In order to improve the efficiency and stability of the device, it may be preferable to replace other stable isotopes in the compound.

[0049] In the compounds referred to herein, multiple substitution refers to a range up to the most available substitution, including double substitution. When a substituent in a compound referred to herein is referred to as multiple substitution (including double substitution, triple substitution, quadruple substitution, etc.), it means that the substituent may be present at multiple available substitution positions on the bond structure, and the substituents present at all available substitution positions may be the same structure or different structures.

[0050] Unless otherwise specified, adjacent substituents in the compounds mentioned herein may be bonded to form a ring. In the compounds mentioned herein, adjacent substituents may be bonded to form a ring, including cases where adjacent substituents are bonded to form a ring, as well as cases where adjacent substituents are not bonded to form a ring. When adjacent substituents are 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 this description, 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.

[0051] 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:

[0052] [ka]

[0053] 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:

[0054] [ka]

[0055] 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.

[0056] [ka]

[0057] According to one embodiment of the present invention, a ligand L having a structure represented by Formula 1 a A metal complex is disclosed, comprising: [ka] (Ring A and Ring B are each independently selected from a 5-membered unsaturated carbocyclic ring, an aromatic ring having 6 to 30 carbon atoms, or a heteroaromatic ring having 3 to 30 carbon atoms; R i are the same or different and represent mono-, multi- or no substitutions at each occurrence, and R ii are the same or different at each occurrence and represent mono-, multi- or no substitution; Y is SiR y R y , GeR y R y , N.R. y , PR y , O, S or Se; The Two R's y When two R y may be the same or different, for example, Y is SiR y R y If selected from two R y may be the same or different, and further, for example, Y may be GeR y R y If selected from two R y may be the same or different, X1~X2 are the same or different for each occurrence. x or selected from N, R, R i , Rii , R x and R y 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 unsubstituted 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 cyano group, an isocyano group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituents R i , R x , R y , R and R ii may be bonded to form a ring, The metal is selected from metals with a relative atomic mass greater than 40.

[0058] In this specification, adjacent substituents R i , R x , R y , R and R ii may be bonded to form a ring means that adjacent substituent groups, for example, two substituents R i two substituents R ii two substituents R y two substituents R x R i and R x Between the substituents R and R y and the substituent R iiand R 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.

[0059] According to one embodiment of the present invention, the metal complex is a The ligand may also include other ligands which may be combined with the ligand to form tridentate, tetradentate, pentadentate or hexadentate ligands.

[0060] According to one embodiment of the present invention, ring A and ring B are each independently selected from a 5-membered unsaturated carbocyclic ring, an aromatic ring having 6 to 18 carbon atoms, or a heteroaromatic ring having 3 to 18 carbon atoms.

[0061] According to one embodiment of the present invention, ring A or ring B is independently selected from a 5-membered unsaturated carbocyclic ring, an aromatic ring having 6 to 18 carbon atoms, or a heteroaromatic ring having 3 to 18 carbon atoms.

[0062] According to one embodiment of the present invention, ring A and ring B are each independently selected from a 5-membered unsaturated carbocyclic ring, an aromatic ring having 6 to 10 carbon atoms, or a heteroaromatic ring having 3 to 10 carbon atoms.

[0063] According to one embodiment of the present invention, ring A or ring B is independently selected from a 5-membered unsaturated carbocyclic ring, an aromatic ring having 6 to 10 carbon atoms, or a heteroaromatic ring having 3 to 10 carbon atoms.

[0064] According to one embodiment of the present invention, the L a is selected from the structures represented by any one of formulas 2 to 19 and formulas 22 to 23. [ka] (In formulas 2 to 19 and formulas 22 to 23, X1 and X2 each independently represent CR x or N, and X3 to X7 are each independently CR i or N, and A1 to A6 are each independently CR iior selected from N, Z may be the same or different for each occurrence. iii R iii , SiR iii R iii , PR iii , O, S or NR iii Selected from two R iii When two R iii are the same or different, for example, Z is CR iii R iii If selected from two R iii are the same or different, and further, for example, Z is SiR iii R iii If selected from two R iii are the same or different, Y is SiR y R y , N.R. y , PR y , O, S or Se, and two R y When two R y may be the same or different, for example, Y is SiR y R y If selected from two R y may be the same or different, R, R i , R ii , R x , R y and R iiiare 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 unsubstituted 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 cyano group, an isocyano group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituents R and R x , R y , R i , R ii , R iii may be bonded to form a ring.

[0065] In this specification, adjacent substituents R and R x , R y , R i , R ii , R iii may be bonded to form a ring means that adjacent substituent groups, for example, two substituents R i two substituents R ii two substituents R x two substituents R y two substituents R iii R i and R x R ii and R iii Between the substituents R and R y R y and R iii and the substituents R and R iiiThis means that any one or more of the substituents may be bonded to form a ring. Obviously, the substituents do not have to be bonded to form a ring.

[0066] According to one embodiment of the present invention, L a is selected from the structures represented by formula 2, formula 9, formula 11, or formula 12.

[0067] According to one embodiment of the present invention, L a is selected from the structure represented by formula 2.

[0068] According to one embodiment of the present invention, in Formulas 2 to 19 and Formulas 22 to 23, X1 to X n and / or A1-A m At least one of the X is selected from N, n corresponds to the largest number in any one of the formulas 2 to 19 and the formulas 22 to 23 of X1 to X7, and A m corresponds to the largest number in any one of the formulas 2 to 19 and the formulas 22 to 23 of A1 to A6. For example, in formula 2, n corresponds to X5, which has the largest number in formula 2 of X1 to X7, and m corresponds to A4 having the largest number among A1 to A6 in formula 2, that is, in formula 2, at least one of X1 to X5 and / or A1 to A4 is selected from N. Furthermore, for example, in formula 12, n corresponds to X3, which has the largest number in formula 12 of X1 to X7, and m corresponds to A4 having the largest number in formula 12 of A1 to A6, that is, in formula 12, at least one of X1 to X3 and / or A1 to A4 is selected from N.

[0069] According to one embodiment of the present invention, in Formulas 2 to 19 and Formulas 22 to 23, X1 to X n At least one of the X is selected from N, ncorresponds to the largest number in any one of formulas 2 to 19 and formulas 22 to 23 of X1 to X7.

[0070] According to one embodiment of the present invention, X2 is N in formulas 2 to 19 and formulas 22 to 23.

[0071] According to one embodiment of the present invention, in Formulas 2 to 19 and Formulas 22 to 23, X1 and X2 are each independently CR x X3 to X7 are each independently selected from CR i A1 to A6 are each independently selected from CR ii and adjacent substituents R x , R i , R ii may be bonded to form a ring.

[0072] In this example, adjacent substituents R x , R i , R ii may be bonded to form a ring means that adjacent substituent groups, for example, two substituents R i two substituents R ii two substituents R x and the substituent R i and R x This means that any one or more of the substituents may be bonded to form a ring. Obviously, the substituents do not have to be bonded to form a ring.

[0073] According to one embodiment of the present invention, in Formulas 2 to 19 and Formulas 22 to 23, X1 and X2 are each independently CR x X3 to X7 are each independently selected from CR i A1 to A6 are each independently selected from CR ii and wherein R x , R i , R iiare 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, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a cyano group, and combinations thereof, and each occurrence of adjacent substituents R x , R i , R ii may be bonded to form a ring.

[0074] According to one embodiment of the present invention, in Formulas 2 to 19 and Formulas 22 to 23, X1 and X2 are each independently CR x X3 to X7 are each independently selected from CR i A1 to A6 are each independently selected from CR ii and wherein R x , R i , R ii at least two of the adjacent substituents R are the same or different and are selected from the group consisting of 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, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a cyano group, and combinations thereof; x , R i , R ii may be bonded to form a ring.

[0075] In this embodiment, the R x , R i , R ii are selected from the above substituent group, the two R x Substituents, all R i Substituents and all R iiIt means that at least two substituents of a group of substituents, at each occurrence, are the same or different and are selected from said group of substituents.

[0076] According to one embodiment of the present invention, in Formulas 2 to 19 and Formulas 22 to 23, X1 and X2 are each independently CR x X3 to X7 are each independently selected from CR i A1 to A6 are each independently selected from CR ii and wherein R x , R i , R ii at least three of the substituents R are the same or different and are selected from the group consisting of 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, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a cyano group, and combinations thereof; x , R i , R ii may be bonded to form a ring.

[0077] In this embodiment, the R x , R i , R ii and at least three of the R x Substituents, all R i Substituents and all R ii It means that at least three substituents of a group of substituents are selected from said group of substituents, either the same or different at each occurrence.

[0078] According to one embodiment of the present invention, in Formulas 2 to 11 and Formulas 22 to 23, X4 and X5 are each independently CR i In formulas 12 to 19, X3 is selected from CR i Selected from.

[0079] According to one embodiment of the present invention, in Formulas 2 to 11 and Formulas 22 to 23, X4 or X5 is CR i In formulas 12 to 19, X3 is selected from CR i Selected from.

[0080] According to one embodiment of the present invention, in Formulas 2 to 11 and Formulas 22 to 23, X4 and X5 are each independently CR i In formulas 12 to 19, X3 is selected from CR i and wherein R i are the same or different at each occurrence and are selected from 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, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a cyano group, or a combination thereof.

[0081] According to one embodiment of the present invention, in Formulas 2 to 11 and Formulas 22 to 23, X4 or X5 is CR i In formulas 12 to 19, X3 is selected from CR i and wherein R i are the same or different at each occurrence and are selected from 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, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a cyano group, or a combination thereof.

[0082] According to one embodiment of the present invention, in Formulas 2 to 11 and Formulas 22 to 23, X4 and X5 are each independently CR i In formulas 12 to 19, X3 is selected from CR i wherein Ri is, each occurrence the same or different, selected from the group consisting of hydrogen, deuterium, fluorine, methyl, ethyl, isopropyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, norbornyl, adamantyl, trimethylsilyl, isopropyldimethylsilyl, phenyldimethylsilyl, trifluoromethyl, cyano, phenyl, and combinations thereof.

[0083] According to one embodiment of the present invention, in Formulas 2 to 11 and Formulas 22 to 23, X4 or X5 is CR i In formulas 12 to 19, X3 is selected from CR i wherein R i is, each occurrence the same or different, selected from the group consisting of hydrogen, deuterium, fluorine, methyl, ethyl, isopropyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, norbornyl, adamantyl, trimethylsilyl, isopropyldimethylsilyl, phenyldimethylsilyl, trifluoromethyl, cyano, phenyl, and combinations thereof.

[0084] According to one embodiment of the present invention, in Formulas 2 to 19 and Formulas 22 to 23, R is selected from 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, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, or a combination thereof.

[0085] According to an embodiment of the present invention, in Formulas 2 to 19 and Formulas 22 to 23, R is selected from hydrogen, deuterium, fluorine, methyl, ethyl, isopropyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, deuterated neopentyl, deuterated cyclopentyl, deuterated cyclopentylmethyl, deuterated cyclohexyl, trimethylsilyl, or a combination thereof.

[0086] According to one embodiment of the present invention, in Formulas 2 to 19 and Formulas 22 to 23, Y is selected from O or S.

[0087] According to one embodiment of the present invention, Y is selected from O in formulas 2 to 19 and formulas 22 to 23.

[0088] According to one embodiment of the present invention, in Formulas 2 to 19 and Formulas 22 to 23, X1 and X2 are each independently CR x Selected from.

[0089] According to one embodiment of the present invention, in Formulas 2 to 19 and Formulas 22 to 23, X1 and X2 are each independently CR x and wherein R x are the same or different at each occurrence and are selected from 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, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, or a combination thereof.

[0090] According to one embodiment of the present invention, in Formulas 2 to 19 and Formulas 22 to 23, X1 is CR x and X2 is N.

[0091] According to one embodiment of the present invention, in Formulas 2 to 19 and Formulas 22 to 23, X1 is CR x X2 is N, and the R x are the same or different at each occurrence and are selected from 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, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, or a combination thereof.

[0092] According to one embodiment of the present invention, the ligand L a has a structure represented by formula 20 or formula 21. [ka] (In Formula 20 and Formula 21, Y is selected from O or S, R x1 , R x2 , R i1 , R i2 , R i3 , R ii1 , R ii2 , R ii3 , R ii4 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 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, or a combination thereof; R, each occurrence, may be the same or different and is 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, 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, and combinations thereof.

[0093] According to one embodiment of the present invention, the ligand L a has a structure represented by formula 20 or formula 21. [ka] (In Formula 20 and Formula 21, Y is selected from O or S, R x1 , R x2 , R i1 , R i2 , R i3 At least one or two of and / or R ii1 , R ii2 , R ii3 , R ii4at least one or two of, each occurrence, are the same or different and are selected from the group consisting of deuterium, halogen, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group of 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group of 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group of 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group of 6 to 20 carbon atoms, or a combination thereof; and R is selected from halogen, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group of 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group of 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group of 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group of 6 to 20 carbon atoms, or a combination thereof.

[0094] According to one embodiment of the present invention, the ligand L a has a structure represented by formula 20 or formula 21. [ka] (In Formula 20 and Formula 21, Y is selected from O or S, R x1 , R x2 , R i1 , R i2 , R i3 At least one or two of and / or R ii1 , R ii2 , R ii3 , R ii4at least one or two of, each occurrence, are the same or different and are selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, or a combination thereof; and R is selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, 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, or a combination thereof.

[0095] According to one embodiment of the present invention, the ligand L a has a structure represented by formula 20 or formula 21. [ka] (In Formula 20 and Formula 21, Y is selected from O or S, R i2 is selected from the group consisting of 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, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, or a combination thereof; R is selected from the group consisting of halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, or a combination thereof; ii1 , R ii2 , R ii3 , R ii4 At least one or two of each occurrence are the same or different and are selected from the group consisting of 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, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, or a combination thereof.

[0096] According to one embodiment of the present invention, the ligand L a has a structure represented by formula 20 or formula 21. [ka] (In Formula 20 and Formula 21, Y is selected from O or S, R i2 is selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, or a combination thereof; R is selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, or a combination thereof; ii1 , R ii2 , R ii3 , R ii4 At least one or two of the groups, which may be the same or different at each occurrence, are selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, or a combination thereof.

[0097] According to one embodiment of the present invention, in Formula 20 and Formula 21, R ii1 , R ii2 , R ii3 One of the following (e.g., R ii1 or R ii2 or R ii3 ) or two (e.g., R ii1 and R ii2 , or R ii2 and R ii3 , or R ii1 and R ii3 ) are the same or different at each occurrence and are selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, or a combination thereof.

[0098] According to one embodiment of the present invention, in Formula 20 and Formula 21, R x1 , R x2 , R i1 , R i2 , R i3 , R ii1 , R ii2 , R ii3 , R ii4 At least one of R, which may be the same or different at each occurrence, is selected from the group consisting of a substituted or unsubstituted alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, and combinations thereof.

[0099] In this example, R x1 , R x2 , R i1 , R i2 , R i3 , R ii1 , R ii2 , R ii3 , R ii4 and at least one of R is selected from the above substituent group, whether identical or different at each occurrence. x1 , R x2 at least one of R i1 , R i2 , R i3 at least one of R ii1 , R ii2 , R ii3 , R ii4 is selected from said substituent group, and / or R is selected from said substituent group.

[0100] According to one embodiment of the present invention, in Formula 20 and Formula 21, R i2 , R i3 , R ii1 , R ii2 , R ii3At least one of R, which may be the same or different at each occurrence, is selected from the group consisting of a substituted or unsubstituted alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, and combinations thereof.

[0101] In this example, R i2 , R i3 , R ii1 , R ii2 , R ii3 and at least one of R is selected from the above substituent group, whether identical or different at each occurrence. i2 , R i3 at least one of R ii1 , R ii2 , R ii3 is selected from said substituent group, and / or R is selected from said substituent group.

[0102] According to one embodiment of the present invention, in Formula 20 and Formula 21, R x1 , R x2 , R i1 , R i2 , R i3 , R ii1 , R ii2 , R ii3 , R ii4 At least one of R, which may be the same or different at each occurrence, is selected from the group consisting of substituted or unsubstituted alkyl groups having 3 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 10 ring carbon atoms, and combinations thereof.

[0103] In this example, R x1 , R x2 , R i1 , R i2 , R i3 , R ii1 , R ii2 , R ii3 , R ii4and at least one of R is selected from the above substituent group, whether identical or different at each occurrence. x1 , R x2 at least one of R i1 , R i2 , R i3 at least one of R ii1 , R ii2 , R ii3 , R ii4 is selected from said substituent group, and / or R is selected from said substituent group.

[0104] According to one embodiment of the present invention, L a may be the same or different for each occurrence of L a1 ~L a1706 The L is selected from the group consisting of a1 ~L a1706 For the specific structure, please refer to claim 14.

[0105] According to one embodiment of the present invention, L a may be the same or different for each occurrence of L a1 ~L a1803 The L is selected from the group consisting of a1 ~L a1803 For the specific structure, please refer to claim 14.

[0106] According to one embodiment of the present invention, L a may be the same or different for each occurrence of L a1 ~L a1931 The L is selected from the group consisting of a1 ~L a1931 For the specific structure, please refer to claim 14.

[0107] According to one embodiment of the present invention, the L a1 ~L a1931 The hydrogen atoms in the structure may be partially or completely substituted with deuterium atoms.

[0108] According to one embodiment of the present invention, the metal complex is M(L a ) m (L b ) n (L c ) q having the structure The metal M is selected from metals with a relative atomic mass greater than 40, and L a , L b and L c are the first, second and third ligands of said metal complex, respectively; m is 1, 2 or 3; n is 0, 1 or 2; q is 0, 1 or 2; m+n+q is equal to the oxidation state of the metal M; and when m is greater than 1, multiple L a are the same or different, and if n is 2, the two L b are the same or different, and if q is 2, the two L c are the same or different, L a , L b and L c may be linked to form multidentate ligands, e.g., L a , L b and L c may be linked to form a tetradentate or hexadentate ligand, and L a , L b and L c may not be linked to form a multidentate ligand, L b and L c is the same or different at each occurrence and is selected from the group consisting of the following structures: [ka] (R a , R b and R c are the same or different at each occurrence and represent mono-, multi- or no substitution; X b are O, S, Se, NR, or the same or different for each occurrence. N1 and CR C1 R C2 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 unsubstituted 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 cyano group, an isocyano group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituents R a , R b , R c , R N1 , R N2 , R C1 and R C2 may be bonded to form a ring.

[0109] In this example, adjacent substituents R a , R b , R c , R N1 , R N2 , R C1 and R C2 may be bonded to form a ring means that adjacent substituent groups, for example, two substituents Ra two substituents R b two substituents R c R a and R b R a and R c R b and R c R a and R N1 R b and R N1 R a and R C1 R a and R C2 R b and R C1 R b and R C2 R a and R N2 R b and R N2 Comrades and R C1 and R C2 This means that any one or more of the substituents may be bonded to form a ring. Obviously, the substituents do not have to be bonded to form a ring.

[0110] In this example, L a , L b and L c may be bonded to form a multidentate ligand means that L a , L b and L c It means that any two or three of L may be linked to form a tetradentate or hexadentate ligand. a , L b and L c may not be linked to form a multidentate ligand.

[0111] According to one embodiment of the invention, the metal M is selected from Ir, Rh, Re, Os, Pt, Au or Cu.

[0112] According to one embodiment of the present invention, the metal M is selected from Ir, Pt or Os.

[0113] According to one embodiment of the present invention, the metal M is Ir.

[0114] According to one embodiment of the present invention, L b is the same or different at each occurrence and is selected from the following structures: [ka] (R1 to R7 each may be the same or different and each represent a hydrogen atom, a deuterium atom, a halogen atom, 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 ...6 to 30 carbon atoms, a The alkyl group is selected from the group consisting of 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 having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof.

[0115] According to one embodiment of the present invention, L b is the same or different at each occurrence and is selected from the following structures: [ka] (At least one of R1 to R3 is selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, or a combination thereof, and / or at least one of R4 to R6 is 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, or a combination thereof.)

[0116] According to one embodiment of the present invention, L b is the same or different at each occurrence and is selected from the following structures: [ka] (At least two of R1 to R3 are selected from the group consisting of substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, or combinations thereof, and / or at least one of R4 to R6 is a 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, or combinations thereof.)

[0117] According to one embodiment of the present invention, L b is the same or different at each occurrence and is selected from the following structures: [ka] (At least two of R1 to R3 are selected from the group consisting of substituted or unsubstituted alkyl groups having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2 to 20 carbon atoms, or combinations thereof, and / or at least two of R4 to R6 are substituted or unsubstituted alkyl groups having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2 to 20 carbon atoms, or combinations thereof.)

[0118] According to one embodiment of the present invention, L b may be the same or different for each occurrence of L b1 ~L b322 and L c may be the same or different for each occurrence of L c1 ~L c231 The L is selected from the group consisting of b1 ~L b322 and L c1 ~L c231 For the specific structure, please refer to claim 18.

[0119] According to one embodiment of the present invention, the metal complex is Ir(L a )2(L b ) or Ir(L a )2(L c ) or Ir(L a )(L c )2 structure.

[0120] The metal complex is Ir(L a )2(L b ), L a may be the same or different for each occurrence of L a1 ~L a1706 and L b L b1 ~L b322 The metal complex is any one selected from the group consisting of Ir(L a )2(L c ), La may be the same or different for each occurrence of L a1 ~L a1706 and L c L c1 ~L c231 The metal complex is any one selected from the group consisting of Ir(L a )(L c )2, L a L a1 ~L a1706 and L c may be the same or different for each occurrence of L c1 ~L c231 Any one or two selected from the group consisting of:

[0121] According to one embodiment of the present invention, the metal complex is Ir(L a )2(L b ) or Ir(L a )2(L c ) or Ir(L a )(L c )2 structure.

[0122] The metal complex is Ir(L a )2(L b ), L a may be the same or different for each occurrence of L a1 ~L a1803 and L b L b1 ~L b322 The metal complex is any one selected from the group consisting of Ir(L a )2(L c ), L a may be the same or different for each occurrence of L a1 ~L a1803 and L c L c1 ~L c231 The metal complex is any one selected from the group consisting of Ir(L a)(L c )2, L a L a1 ~L a1803 and L c may be the same or different for each occurrence of L c1 ~L c231 Any one or two selected from the group consisting of:

[0123] According to one embodiment of the present invention, the metal complex is Ir(L a )2(L b ) or Ir(L a )2(L c ) or Ir(L a )(L c )2 structure.

[0124] The metal complex is Ir(L a )2(L b ), L a may be the same or different for each occurrence of L a1 ~L a1931 and L b L b1 ~L b322 The metal complex is any one selected from the group consisting of Ir(L a )2(L c ), L a may be the same or different for each occurrence of L a1 ~L a1931 and L c L c1 ~L c231 The metal complex is any one selected from the group consisting of Ir(L a )(L c )2, L a L a1 ~L a1931 and L c may be the same or different for each occurrence of L c1 ~L c231Any one or two selected from the group consisting of:

[0125] According to one embodiment of the present invention, the metal complex is selected from the group consisting of Compound 1 to Compound 260. For specific structures of Compound 1 to Compound 260, please refer to claim 19.

[0126] According to one embodiment of the present invention, the metal complex is selected from the group consisting of Compound 1 to Compound 290. For specific structures of Compound 1 to Compound 290, please refer to claim 19.

[0127] According to one embodiment of the present invention, the metal complex is selected from the group consisting of Compound 1 to Compound 312. For specific structures of Compound 1 to Compound 312, please refer to claim 19.

[0128] According to one embodiment of the present invention, there is disclosed an electroluminescent device including an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer contains a ligand L having a structure represented by Formula 1: a The present invention also includes metal complexes comprising: [ka] (Ring A and Ring B are each independently selected from a 5-membered unsaturated carbocyclic ring, an aromatic ring having 6 to 30 carbon atoms, or a heteroaromatic ring having 3 to 30 carbon atoms; R i are the same or different and represent mono-, multi- or no substitutions at each occurrence, and R ii are the same or different at each occurrence and represent mono-, multi- or no substitution; Y is SiR y R y , GeR y R y , N.R. y , PR y , O, S or Se; The Two R's y When two R y may be the same or different, X1~X2 are the same or different for each occurrence. x or selected from N, R, R i , R ii , R x and R y 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 unsubstituted 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 cyano group, an isocyano group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituents R i , R x , R y , R and R ii may be bonded to form a ring, The metal is selected from metals with a relative atomic mass greater than 40.

[0129] According to an embodiment of the present invention, in the electroluminescent device, the organic layer is a light-emitting layer and the metal complex is a light-emitting material.

[0130] According to one embodiment of the present invention, the electroluminescent element emits red light.

[0131] According to one embodiment of the present invention, the electroluminescent element emits white light.

[0132] According to an embodiment of the present invention, in the electroluminescent device, the organic layer is an emitting layer, and the emitting layer further comprises at least one host material.

[0133] According to one embodiment of the present invention, in the electroluminescent device, the at least one 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.

[0134] According to another embodiment of the present invention, there is further disclosed a combination of compounds comprising a metal complex, the specific structure of which is shown in any one of the above-mentioned embodiments.

[0135] Combination with other materials

[0136] 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.

[0137] It is noted herein that specific layer materials used in organic light-emitting devices can be used in combination with a variety of other materials present in the device. Illustratively, the light-emitting dopants disclosed herein can be used in combination with a variety of 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.

[0138] 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, a differential scanning calorimeter, a Shanghai Liangguang Technology fluorescence spectrophotometer, a Wuhan Science & Technology electrochemical work station, and an Anhui Beike sublimation apparatus) in a manner familiar to those skilled in the art. In the device examples, the device properties were also tested using instruments commonly used in the art (including, but not limited to, an evaporator from Angstrom Engineering, an optical test system, a service life test system from Suzhou Fusida, an ellipsometer from Beijing Liangguang), 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.

[0139] Examples of material synthesis

[0140] The preparation method of the compound according to the present invention is not limited. Taking the following compound as a typical but non-limiting example, its synthetic route and preparation method are as follows:

[0141] Synthetic Example 1: Synthesis of Compound 81

[0142] Step 1: Synthesis of intermediate 2 [ka] 5 g of starting material 1 (24.03 mmol) was dissolved in 50 mL of DCM. 5.39 g (1.3 eq, 31.24 mmol) of m-CPBA (m-chloroperoxybenzoic acid) was added at room temperature and stirred for 24 h. After TLC showed the disappearance of the starting material, the solvent was removed in vacuo. The crude intermediate 2 obtained could be used directly in the next reaction.

[0143] Step 2: Synthesis of intermediate 3 [ka] Intermediate 2 obtained in step 1 was dissolved in 24 mL of phosphorus oxychloride. The mixture was heated to 100 °C, stirred for 3 h, and cooled to 0 °C. Aqueous NaOH solution was slowly added dropwise until the pH reached 9, and the mixture was extracted three times with DCM (50 mL * 3). The organic phases were combined, washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed in vacuo. Purification by column chromatography (PE:EA = 30:1) gave 1.98 g of intermediate 3, a 34% yield for the two steps.

[0144] Step 3: Synthesis of Intermediate 5 [ka] 3 g (18.96 mmol) of intermediate 4 was dissolved in 30 mL of anhydrous tetrahydrofuran and cooled to -78 °C. Under a nitrogen atmosphere, n-BuLi (1 M, 22.75 mL) (1.2 eq, 22.75 mmol) was slowly added dropwise. After the addition was complete, the mixture was allowed to warm to room temperature and stirred for 1 h. After the mixture was cooled to -78 °C, 4.63 g (1.3 eq, 24.65 mmol) of 1,2-dibromoethane was slowly added dropwise. After the addition was complete, the mixture was allowed to warm to room temperature and stirred overnight. The reaction was quenched by the addition of saturated ammonium chloride. The mixture was extracted three times with EA (40 mL * 3). The organic phases were combined, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and the solvent was removed in vacuo. Purification by column chromatography (PE:EA = 100:1) afforded 3.82 g of intermediate 5 in an 85% yield.

[0145] Step 4: Synthesis of intermediate 6 [ka] 2.5 g of intermediate 5 (10.57 mmol), 0.387 g of PdCl(dppf) (0.05 eq, 0.53 mmol), 1.56 g of AcOK (1.5 eq, 15.85 mmol), and 3.22 g of B2Pin2 (bis(pinacolato)diboron) (1.2 eq, 12.68 mmol) were dissolved in 30 mL of 1,4-dioxane, heated to 80 °C, and stirred overnight. After cooling to room temperature, the solvent was removed in vacuo. Purification by column chromatography (PE:EA = 20:1) gave 2.21 g of intermediate 6 as a white solid, 74% yield.

[0146] Step 5: Synthesis of Intermediate 7 [ka] 3.93 g of intermediate 6 (1.2 eq, 13.85 mmol), 2.78 g of intermediate 3 (1 eq, 11.54 mmol), 0.387 g of Pd(PPh3)4 (0.05 eq, 0.58 mmol), and 1.83 g of Na2CO3 (1.5 eq, 17.31 mmol) were dissolved in 30 mL of 1,4-dioxane and 10 mL of water, heated to 90 °C, and stirred overnight. After cooling to room temperature, the solvent was removed in vacuo. Purification by column chromatography (PE:EA = 50:1) gave 3 g of intermediate 7 as a white solid, 72% yield.

[0147] Step 6: Synthesis of Intermediate 8 [ka] 3.03 g of intermediate 7 (8.32 mmol) was dissolved in 30 mL of DCM and cooled to 0 °C. Under a nitrogen atmosphere, BBr3 was slowly added dropwise and stirred for 2 h. The reaction was quenched by the addition of aqueous NaHCO3 solution. Extraction was performed with DCM (60 mL * 3), and the organic phases were combined, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and the solvent was removed in vacuo. Purification by column chromatography (PE:EA = 4:1) gave 1.17 g of intermediate 8, a 40% yield.

[0148] Step 7: Synthesis of Intermediate 9 [ka] 1.2 g of intermediate 8 (1 eq, 3.33 mmol), 24 mg of CuBr (0.05 eq, 0.17 mmol), and 2.82 g of KPO (4 eq, 13.3 mmol) were dissolved in 15 mL of DMF, heated to 90 °C, and stirred overnight. After cooling to room temperature, the mixture was diluted with water to precipitate the product, filtered through diatomaceous earth, and washed with 1 L of DCM. 0.81 g of intermediate 9 was obtained, for a yield of 90%. The resulting yellow solid, intermediate 9, was recrystallized from toluene. The purity of the resulting solid, intermediate 9, was 99.7%.

[0149] Step 8: Synthesis of the iridium dimer [ka] At room temperature, 1.2 g (3 eq, 4.45 mmol) of intermediate 9 was dissolved in 24 mL of 2-ethoxyethanol and 8 mL of water, followed by the addition of 523 mg of IrCl3·3H2O (1 eq, 1.48 mmol). The mixture was purged with nitrogen gas three times and heated to 130 °C. The mixture was refluxed at this temperature for 24 hours and then cooled to room temperature. After filtration, the solid was washed with ethanol until the washings were colorless. The solid was suction filtered for approximately 15 minutes until the ethanol on top of the solid was completely removed, yielding 1.13 g of a red solid, iridium dimer, in 99% yield. No purification was required; the product could be used directly in the next reaction.

[0150] Step 9: Synthesis of Compound 81 [ka] 1.13 g of the iridium dimer (1 eq, 0.74 mmol) obtained in Step 8 was added to a 100 mL round-bottom flask, followed by 510 mg of K2CO3 (5 eq, 3.7 mmol) and 0.74 g of 3,7-diethyl-3-methyl-4,6-nonanedione (4 eq, 2.96 mmol). The mixture was purged with nitrogen gas three times at room temperature and stirred for 24 hours under nitrogen gas protection. The mixture was filtered through diatomaceous earth, washed with ethanol until the washings were colorless, and then suction filtered for approximately 15 minutes to remove the ethanol adsorbed on the solid. The red solid on the diatomaceous earth was dissolved in 200 mL of dichloromethane under vacuum suction filtering conditions. 20 mL of ethanol was added to the flask, and the dichloromethane was removed under vacuum. The product was precipitated in the remaining ethanol, filtered, and pumped to dry the ethanol adsorbed on the solid. The crude solid was purified by silica gel column chromatography (PE:DCM=10:1). The resulting crude solid was dissolved in 200 mL of dichloromethane, 20 mL of ethanol was added, and the dichloromethane was removed under vacuum. The product was precipitated in the remaining ethanol, filtered, and pumped to dry the ethanol adsorbed on the solid, yielding Compound 81 (mass 1.13 g, yield 80%) as a red solid. The purity was 99.6%. The product was confirmed to be the target product with a molecular weight of 954.3.

[0151] Synthesis Example 2: Synthetic Compound 83

[0152] Step 1: Synthesis of intermediate 11 [ka] Intermediate 10 (7.6 g, 35.1 mmol) was dissolved in 70 mL of ultra-dry tetrahydrofuran and the reaction solution was cooled to 0 °C. Then, under nitrogen gas protection, n-butyllithium solution (15.5 mL, 38.7 mmol) was added dropwise. After the addition was complete, the mixture was maintained at this temperature for 1 h. Then, isopropoxypinacolboronate (iPrOBpin, 8.49 g, 45.6 mmol) was added. After the addition was complete, the reaction was allowed to warm to room temperature and react for 2 h. The reaction was then quenched by adding saturated ammonium chloride solution. Ethyl acetate was added to the reaction, and the solution was separated. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined, dried, and then rotary evaporated to completely remove the solvent to obtain the crude product. Separation by silica gel column chromatography (eluent: ethyl acetate:petroleum ether=1:50, v / v) gave the target product, Intermediate 11 (4.7 g, yield 39.1%), as a colorless oily liquid.

[0153] Step 2: Synthesis of intermediate 13 [ka] Intermediate 12 (3.19 g, 13.7 mmol), Intermediate 11 (4.7 g, 13.7 mmol), tetratriphenylphosphine palladium (0.8 g, 0.69 mmol), sodium carbonate (2.18 g, 20.55 mmol), 1,4-dioxane (60 mL), and water (15 mL) were added to a 250 mL round-bottom flask. The reaction was then heated to 80 °C under nitrogen gas protection and stirred overnight. After TLC showed the reaction was complete, it was allowed to cool to room temperature. Ethyl acetate was then added to the reaction, and the solution was separated. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined, dried, and spun to completely remove the solvent by rotary evaporation to obtain the crude product. Silica gel column chromatography (eluent: ethyl acetate:petroleum ether = 1:10, v / v) gave the desired product as a white solid, Intermediate 13 (3.5 g, 73.0% yield).

[0154] Step 3: Synthesis of intermediate 14 [ka] Intermediate 13 (4.1 g, 10 mmol) was dissolved in 20 mL of ethanol. 20 mL of 2 M HCl was then added, and the reaction was heated to reflux and stirred overnight. After TLC showed the reaction was complete, it was cooled to room temperature. Saturated sodium carbonate solution was then added to adjust the pH to neutral. A large amount of yellow solid precipitated from the solution. After filtration, the solid was washed with water multiple times and then pumped to dryness to obtain the desired product, Intermediate 14 (3.3 g, 93.2% yield), as a yellow solid.

[0155] Step 4: Synthesis of intermediate 15 [ka] Intermediate 14 (3.3 g, 9.3 mmol), cuprous bromide (133 mg, 0.9 mmol), 2,2,6,6-tetramethylheptanedione (1.37 g, 7.44 mmol), cesium carbonate (7.6 g, 23.25 mmol), and DMF (90 mL) were heated to 135 °C under nitrogen gas protection and reacted overnight. After TLC showed the reaction was complete, the mixture was cooled to room temperature. 200 mL of water was added until a large amount of yellow solid precipitated in the solution, which was then filtered. The solid was washed several times with water and then pumped to dryness to obtain the desired product, Intermediate 15 (3.10 g, 96% yield), as a yellow solid.

[0156] Step 5: Synthesis of intermediate 16 [ka] Intermediate 15 (3.42 g, 10.8 mmol), isobutyl borate (2.2 g, 21.6 mmol), palladium acetate (121 mg, 0.54 mmol), Sphos (443 mg, 1.08 mmol), potassium phosphate trihydrate (8.63 g, 32.4 mmol), and toluene (80 mL) were heated to reflux under nitrogen gas protection and reacted overnight. After TLC showed the reaction was complete, the mixture was cooled to room temperature and filtered through a diatomaceous earth funnel. The filtrate was collected and spun to completely remove the solvent by rotary evaporation. The crude product was separated by silica gel column chromatography (eluent: ethyl acetate:petroleum ether = 1:30, v / v) to give the desired product as a yellow solid, intermediate 16 (1.8 g, 49.4% yield).

[0157] Step 6: Synthesis of the iridium dimer [ka] A mixture of intermediate 16 (1.8 g, 5.3 mmol), iridium trichloride trihydrate (628 mg, 1.78 mmol), 2-ethoxyethanol (21 mL), and water (7 mL) was refluxed under nitrogen for 24 hours. After cooling to room temperature, the solution was carefully spun on an evaporator to remove the water, yielding an ethoxyethanol solution of the iridium dimer, which could be used in the next reaction without further purification.

[0158] Step 7: Synthesis of Compound 83 [ka] A solution of iridium dimer, 3,7-diethyl-3-methylnonane-4,6-dione (663 mg, 2.67 mmol), and potassium carbonate (1.23 g, 8.9 mmol) was added to a 100 mL round-bottom flask and reacted at 60 °C for 24 hours under nitrogen gas protection. It was then poured into a diatomaceous earth funnel, filtered, and washed with ethanol. Dichloromethane was added to the resulting solid, and the filtrate was collected. Ethanol was then added, and the resulting solution was concentrated, but not completely. After filtration, 1.1 g of the product, Compound 83, was obtained, with a yield of 57%. The product was further purified by column chromatography. NMR and LC-MS confirmed the compound to be the target product with a molecular weight of 1094.5.

[0159] Synthetic Example 3: Synthesis of Compound 64

[0160] Step 1: Synthesis of intermediate 18 [ka] Intermediate 17 (2.93 g, 12.54 mmol), Intermediate 11 (3.9 g, 11.4 mmol), Pd(dppf)Cl2 (439 mg, 0.6 mmol), and K2CO3 (4.73 g, 34.2 mmol) were mixed in dioxane / water (42 mL / 14 mL). After purging with nitrogen gas, the mixture was allowed to react at room temperature overnight. The mixture was filtered through diatomaceous earth and extracted three times with EA. The organic phases were combined, concentrated, and purified by column chromatography to give Intermediate 18 (3 g, 63.7% yield).

[0161] Step 2: Synthesis of intermediate 20 [ka] Intermediate 18 (3.8 g, 9.2 mmol) was added to a mixture of 12 N HCl (7.6 mL) and MeOH (20 mL) and reacted at 54 °C for 2 h. After completion of the reaction was confirmed by TLC, the mixture was cooled to room temperature and saturated NaHCO3 solution was added to adjust the pH to approximately 7-8. After extraction with EA three times, the organic phases were combined, washed with saturated aqueous sodium chloride, and concentrated to obtain crude intermediate 19, which could be used directly in the next reaction without further purification. The crude intermediate 19 (2.6 g, 7.2 mmol), CuBr (103 mg, 0.72 mmol), 2,2,6,6-tetramethyl-3,5-heptanedione (1.06 g, 5.76 mmol), and Cs2CO3 (5.87 g, 18 mmol) were mixed in DMF (72 mL). After purging with nitrogen gas, the mixture was reacted overnight. After cooling to room temperature, the product was filtered and the filter cake was washed with a suitable amount of DMF, followed by EtOH and PE, and dried to give intermediate 20 (1.85 g, 63% yield in two steps).

[0162] Step 3: Synthesis of intermediate 21 [ka] Intermediate 20 (1.85 g, 5.82 mmol), isobutylboronic acid (1.19 g, 11.64 mmol), Pd(OAc) (65 mg, 0.29 mmol), sphos (238 mg, 0.58 mmol), and KPO 3HO (4.66 g, 17.5 mmol) were dissolved in toluene (58 mL). The reaction was refluxed at 120 °C under nitrogen gas protection. After complete conversion of intermediate 21 was detected by HPLC, the reaction solution was cooled to room temperature, filtered through diatomaceous earth, concentrated, and purified by column chromatography to give intermediate 21 (1.3 g of a yellow solid, 66% yield).

[0163] Step 4: Synthesis of compound 64 [ka] Intermediate 21 (825 mg, 2.42 mmol), IrCl3·3H2O (286 mg, 0.81 mmol), ethoxyethanol (11.5 mL), and water (3.5 mL) were weighed and added to a 100 mL one-neck flask. After purging with nitrogen gas, the reaction was refluxed at 130 °C for 24 hours. After the reaction was cooled to room temperature, the resulting precipitate was filtered, and the filter cake was washed with ethanol and dried. The resulting iridium dimer, 3,7-diethyl-1,1,1-trifluorononane-4,6-dione (319 mg, 1.2 mmol), and K2CO3 were then added. 3( A 100 mL single-neck flask was mixed with 560 mg (4.05 mmol) of ethoxyethanol (13 mL). After purging with nitrogen gas, the mixture was allowed to react at room temperature overnight. After TLC confirmed the reaction was complete, stirring was stopped. The reaction solution was filtered through diatomaceous earth, the filter cake was washed with an appropriate amount of EtOH, and the crude product was rinsed with DCM into a 250 mL eggplant-shaped flask. EtOH (approximately 5 mL) was added, and the DCM was removed by rotation at room temperature. The precipitated solid was filtered and washed with an appropriate amount of EtOH to obtain the product, Compound 64 (80 mg, 8.7% yield). The product was confirmed to be the target product with a molecular weight of 1136.4.

[0164] Synthetic Example 4: Synthesis of Compound 93

[0165] Step 1: Synthesis of iridium dimer [ka] A mixture of intermediate 22 (0.76 g, 1.92 mmol), iridium trichloride trihydrate (226 mg, 0.64 mmol), 2-ethoxyethanol (7.5 mL), and water (2.5 mL) was refluxed under a nitrogen atmosphere for 24 hours. After cooling to room temperature, the water in the solution was carefully removed by rotation in an evaporator to obtain an ethoxyethanol solution of the iridium dimer. This solution could be used directly in the next reaction without further purification.

[0166] Step 2: Synthesis of Compound 93 [ka] The ethoxyethanol solution of the iridium dimer obtained in the above step, 3,7-diethyl-3-methylnonane-4,6-dione (450 mg, 1.84 mmol), and potassium carbonate (0.64 g, 4.45 mmol) were added to a 25 mL round-bottom flask and reacted at 50 °C for 24 hours under nitrogen gas protection. The mixture was then poured into a diatomaceous earth funnel, filtered, and washed with ethanol. Dichloromethane was added to the resulting solid, and the filtrate was collected. Ethanol was then added, and the resulting solution was concentrated, but not completely. After filtration, 550 mg of the product, Compound 93, was obtained, with a yield of 71%. LC-MS confirmed that the compound was the target product with a molecular weight of 1206.6.

[0167] Synthetic Example 5: Synthesis of Compound 117

[0168] Step 1: Synthesis of iridium dimer [ka] Intermediate 23 (2.1 g, 5.56 mmol), iridium trichloride trihydrate (494 mg, 1.4 mmol), ethoxyethanol (18 mL), and water (6 mL) were weighed and added to a 250 mL one-neck flask. After purging with nitrogen gas, the reaction was refluxed at 130 °C for 24 hours. After cooling to room temperature, the resulting precipitate was filtered, washed with ethanol, and dried to obtain the iridium dimer. This product could be used directly in the next reaction without further purification.

[0169] Step 2: Synthesis of compound 117 [ka] The prepared iridium dimer, 3,7-diethyl-3,7-dimethyl-4,6-nonanedione (421 mg, 1.75 mmol), potassium carbonate (1.94 g, 14 mmol), and ethoxyethanol (24 mL) were mixed in a 100 mL single-neck flask. After purging with nitrogen gas, the mixture was reacted at 55 °C overnight. After completion of the reaction was confirmed by TLC, stirring was stopped. The reaction solution was filtered through diatomaceous earth, the filter cake was washed with an appropriate amount of ethanol, and the crude product was rinsed with dichloromethane into a 250 mL eggplant-shaped flask. Ethanol (approximately 5 mL) was added, and the dichloromethane was removed by rotary evaporation at room temperature. The solid was precipitated, filtered, washed with an appropriate amount of ethanol, dried, and then dissolved in dichloromethane. After concentration, column chromatography yielded compound 117 (1 g, 60% yield) as a red solid with a purity of 99.4%. The compound was identified as the target product with a molecular weight of 1192.6 by LC-MS.

[0170] Synthetic Example 6: Synthesis of Compound 116

[0171] Step 1: Synthesis of iridium dimer [ka] A mixture of intermediate 24 (1.37 g, 3.73 mmol), iridium trichloride trihydrate (329 mg, 0.93 mmol), 2-ethoxyethanol (12 mL), and water (4 mL) was refluxed under nitrogen for 24 hours. After cooling to room temperature, the iridium dimer was obtained as a red solid by filtration. It was used directly in the next reaction without further purification.

[0172] Step 2: Synthesis of Compound 116 [ka] The iridium dimer obtained in the above step, 3,7-diethyl-3,7-dimethylnonane-4,6-dione (430 mg, 1.79 mmol), and potassium carbonate (0.62 g, 4.48 mmol) were added to a 50 mL round-bottom flask and reacted at 50 °C for 24 hours under nitrogen gas protection. The mixture was then poured into a diatomaceous earth funnel, filtered, and washed with ethanol. Dichloromethane was added to the resulting solid, and the filtrate was collected. Ethanol was then added, and the resulting solution was concentrated, but not completely. After filtration, 810 mg of the product, compound 116, was obtained, with a yield of 82.2%. LC-MS confirmed that the compound was the target product with a molecular weight of 1164.5.

[0173] Synthetic Example 7: Synthesis of Compound 261

[0174] Step 1: Synthesis of iridium dimer [ka] A mixture of intermediate 25 (0.76 g, 1.92 mmol), iridium trichloride trihydrate (226 mg, 0.64 mmol), 2-ethoxyethanol (7.5 mL), and water (2.5 mL) was refluxed under nitrogen for 24 hours. After cooling to room temperature, the water in the solution was carefully removed by spinning in an evaporator to obtain an ethoxyethanol solution of the iridium dimer. This solution could be used directly in the next reaction without further purification.

[0175] Step 2: Synthesis of Compound 261 [ka] The ethoxyethanol solution of the iridium dimer obtained in the above step, 3,7-diethyl-3,7-dimethylnonane-4,6-dione (450 mg, 1.84 mmol), and potassium carbonate (0.64 g, 4.45 mmol) were added to a 25 mL round-bottom flask and reacted at 50 °C for 24 hours under nitrogen gas protection. The mixture was then poured into a diatomaceous earth funnel, filtered, and washed with ethanol. Dichloromethane was added to the solid and the filtrate was collected. Ethanol was then added, and the resulting solution was concentrated, but not completely. After filtration, 1.75 g of the product, compound 261, was obtained, with a yield of 96%. LC-MS confirmed that the compound was the target product with a molecular weight of 1220.6.

[0176] Synthetic Example 8: Synthesis of Compound 262

[0177] Step 1: Synthesis of iridium dimer [ka] A mixture of intermediate 26 (0.76 g, 1.92 mmol), iridium trichloride trihydrate (226 mg, 0.64 mmol), 2-ethoxyethanol (7.5 mL), and water (2.5 mL) was refluxed under nitrogen for 24 hours. After cooling to room temperature, the water in the solution was carefully removed by spinning in an evaporator to obtain an ethoxyethanol solution of the iridium dimer. This solution could be used directly in the next reaction without further purification.

[0178] Step 2: Synthesis of Compound 262 [ka] The ethoxyethanol solution of the iridium dimer obtained in the above step, 3,7-diethyl-1,1,1-trifluorononane-4,6-dione (450 mg, 1.84 mmol), and potassium carbonate (0.64 g, 4.45 mmol) were added to a 25 mL round-bottom flask and reacted at 50 °C for 24 hours under nitrogen gas protection. The mixture was then poured into a diatomaceous earth funnel, filtered, and washed with ethanol. Dichloromethane was added to the solid and the filtrate was collected. Ethanol was then added, and the resulting solution was concentrated, but not completely. After filtration, 1.35 g of the product, compound 262, was obtained, with a purity of 98.86% and a yield of 92%. LC-MS confirmed that the compound was the target product with a molecular weight of 1246.5.

[0179] Synthetic Example 9: Synthesis of Compound 264

[0180] Step 1: Synthesis of iridium dimer [ka] Intermediate 27 (800 mg, 2.1 mmol), iridium trichloride trihydrate (250 mg, 0.7 mmol), ethoxyethanol (7.5 mL), and water (2.5 mL) were added to a 100 mL single-neck flask. After purging with nitrogen gas, the reaction was refluxed at 130 °C for 24 hours. After cooling, the reaction was concentrated and the solvent was removed by spinning to obtain the iridium dimer. This product could be used directly in the next reaction without further purification.

[0181] Step 2: Synthesis of Compound 264 [ka] 3,7-Diethyl-3,7-dimethylnonane-4,6-dione (337 mg, 1.4 mmol), potassium carbonate (967 mg, 7 mmol), and ethoxyethanol (14 mL) were added to the iridium dimer obtained in the above step. After purging with nitrogen gas, the reaction was allowed to proceed at room temperature for 48 hours. The reaction solution was filtered through diatomaceous earth, the filter cake was washed with an appropriate amount of ethanol, and the crude product was rinsed with dichloromethane into a 250 mL recovery flask. Ethanol (approximately 5 mL) was added, and the dichloromethane was removed by rotary evaporation at room temperature. The solid was precipitated, filtered, washed with an appropriate amount of ethanol, dried, and then dissolved in dichloromethane. After concentration, the mixture was purified by column chromatography to obtain compound 264 (570 mg). LC-MS confirmed that this compound was the target product with a molecular weight of 1192.6.

[0182] Synthetic Example 10: Synthesis of Compound 263

[0183] Step 1: Synthesis of iridium dimer [ka] A mixture of intermediate 28 (0.46 g, 1.28 mmol), iridium trichloride trihydrate (130 mg, 0.37 mmol), 2-ethoxyethanol (4.5 mL), and water (1.5 mL) was refluxed under nitrogen for 24 hours. After cooling to room temperature, the iridium dimer was obtained as a red solid by filtration, which could be used directly in the next reaction without further purification.

[0184] Step 2: Synthesis of compound 263 [ka] The iridium dimer obtained in the above step, 3,7-diethyl-3,7-dimethylnonane-4,6-dione (133 mg, 0.55 mmol), and potassium carbonate (0.25 g, 1.84 mmol) were added to a 50 mL round-bottom flask and reacted at 40 °C for 24 hours under nitrogen gas protection. The mixture was then poured into a diatomaceous earth funnel, filtered, and washed with ethanol. Dichloromethane was added to the resulting solid, and the filtrate was collected. Ethanol was then added, and the resulting solution was concentrated, but not completely. After filtration, 300 mg of the product, compound 263, was obtained, with a yield of 73.7%. LC-MS confirmed that the compound was the target product with a molecular weight of 1164.5.

[0185] Synthetic Example 11: Synthesis of Compound 266

[0186] Step 1: Synthesis of iridium dimer [ka] A mixture of intermediate 29 (1.45 g, 3.42 mmol), iridium trichloride trihydrate (346 mg, 0.98 mmol), 2-ethoxyethanol (12 mL), and water (4 mL) was refluxed under nitrogen for 24 hours. After cooling to room temperature, the iridium dimer was obtained as a red solid by filtration. It was used directly in the next reaction without further purification.

[0187] Step 2: Synthesis of Compound 266 [ka] The iridium dimer (0.67 g, 0.31 mmol) obtained in the above step, 3,7-diethyl-3-methylnonane-4,6-dione (0.21 g, 0.94 mmol), and potassium carbonate (0.43 g, 3.1 mmol) were dissolved in 9 mL of ethoxyethanol and reacted at 40 °C for 24 hours under nitrogen gas protection. The mixture was then poured into a diatomaceous earth funnel, filtered, and washed with ethanol. Dichloromethane was added to the resulting solid, and the filtrate was collected. Ethanol was then added, and the resulting solution was concentrated, but not completely. After filtration, 370 mg of compound 266 was obtained, with a yield of 47.3%. LC-MS confirmed that the compound was the target product with a molecular weight of 1262.6.

[0188] Synthetic Example 12: Synthesis of Compound 265

[0189] Step 1: Synthesis of Compound 265 [ka] Iridium dimer (0.67 g, 0.31 mmol), intermediate 30 (0.21 g, 0.94 mmol), and potassium carbonate (0.43 g, 3.1 mmol) were dissolved in 9 mL of ethoxyethanol and reacted at 40 °C for 24 hours under nitrogen gas protection. The mixture was then poured into a diatomaceous earth funnel, filtered, and washed with ethanol. Dichloromethane was added to the resulting solid, and the filtrate was collected. Ethanol was then added, and the resulting solution was concentrated, but not completely. After filtration, 370 mg of compound 265 was obtained, with a yield of 47.3%. LC-MS confirmed this compound to be the target product with a molecular weight of 1302.6.

[0190] Synthetic Example 13: Synthesis of Compound 267

[0191] Step 1: Synthesis of iridium dimer [ka] A mixture of intermediate 31 (0.6 g, 1.68 mmol), iridium trichloride trihydrate (198 mg, 0.56 mmol), 2-ethoxyethanol (7.5 mL), and water (2.5 mL) was refluxed under nitrogen for 24 hours. After cooling to room temperature, the iridium dimer was obtained as a red solid by filtration. It was used directly in the next reaction without further purification.

[0192] Step 2: Synthesis of compound 267 [ka] The iridium dimer obtained in the above step, 3,7-diethyl-3,7-dimethylnonane-4,6-dione (270 mg, 1.12 mmol), and potassium carbonate (0.77 g, 5.6 mmol) were added to a 25 mL round-bottom flask and reacted at 50 °C for 24 hours under nitrogen gas protection. The mixture was then poured into a diatomaceous earth funnel, filtered, and washed with ethanol. Dichloromethane was added to the resulting solid, and the filtrate was collected. Ethanol was then added, and the resulting solution was concentrated, but not completely. After filtration, 0.4 g of crude product was obtained, with a purity of 91.6%. The product was further purified by column chromatography to obtain 0.3 g of the final product, compound 267, with a yield of 47%. LC-MS confirmed the compound as the target product with a molecular weight of 1136.5.

[0193] Synthetic Example 14: Synthesis of Compound 269

[0194] Step 1: Synthesis of iridium dimer [ka] A mixture of intermediate 32 (1.5 g, 4.2 mmol), iridium trichloride trihydrate (427 mg, 1.2 mmol), 2-ethoxyethanol (12 mL), and water (4 mL) was refluxed under nitrogen for 24 hours. After cooling to room temperature, the iridium dimer was obtained as a red solid by filtration. It was used directly in the next reaction without further purification.

[0195] Step 2: Synthesis of Compound 269 [ka] The iridium dimer obtained in the above step, 3,7-diethyl-3,7-dimethylnonane-4,6-dione (580 mg, 2.4 mmol), and potassium carbonate (0.83 g, 6.04 mmol) were dissolved in 16 mL of ethoxyethanol and reacted at 40 °C for 24 hours under nitrogen gas protection. The mixture was then poured into a funnel containing diatomaceous earth, filtered, and washed with ethanol. Dichloromethane was added to the resulting solid, and the filtrate was collected. Ethanol was then added, and the resulting solution was concentrated, but not completely. After filtration, 940 mg of compound 269 was obtained, representing a yield of 66%. LC-MS confirmed that this compound was the target product with a molecular weight of 1166.5.

[0196] Synthetic Example 15: Synthesis of Compound 288

[0197] Step 1: Synthesis of iridium dimer [ka] A mixture of intermediate 33 (1.2 g, 2.93 mmol), iridium trichloride trihydrate (427 mg, 1.2 mmol), 2-ethoxyethanol (12 mL), and water (4 mL) was refluxed under nitrogen for 24 hours. After cooling to room temperature, the iridium dimer was obtained as a red solid by filtration. It was used directly in the next reaction without further purification.

[0198] Step 2: Synthesis of compound 288 [ka] The iridium dimer (0.67 g, 0.31 mmol) obtained in the above step, intermediate 34 (414 mg, 1.76 mmol), and sodium hydroxide (176 mg, 4.4 mmol) were dissolved in 16 mL of ethoxyethanol and reacted at 40 °C for 24 hours under nitrogen gas protection. The mixture was then poured into a diatomaceous earth funnel, filtered, and washed with ethanol. Dichloromethane was added to the resulting solid, and the filtrate was collected. Ethanol was then added, and the resulting solution was concentrated, but not completely. After filtration, 410 mg of compound 288 was obtained, with a yield of 27.4%. LC-MS confirmed that this compound was the target product with a molecular weight of 1248.6.

[0199] Synthetic Example 16: Synthesis of Compound 273

[0200] Step 1: Synthesis of iridium dimer [ka] A mixture of intermediate 35 (1.3 g, 3.54 mmol), iridium trichloride trihydrate (204 mg, 0.58 mmol), 2-ethoxyethanol (18 mL), and water (6 mL) was refluxed under nitrogen for 24 hours. After cooling to room temperature, the iridium dimer was obtained as a red solid by filtration. It was used directly in the next reaction without further purification.

[0201] Step 2: Synthesis of compound 273 [ka] The iridium dimer obtained in the above step, 3,7-diethyl-3,7-dimethylnonane-4,6-dione (0.21 g, 0.87 mmol), and potassium carbonate (0.40 g, 2.9 mmol) were added to a 100 mL round-bottom flask and reacted at 50 °C for 24 hours under nitrogen gas protection. The mixture was then poured into a diatomaceous earth funnel, filtered, and washed with ethanol. Dichloromethane was added to the resulting solid, and the filtrate was collected. Ethanol was then added, and the resulting solution was concentrated, but not completely. After filtration, 0.7 g of crude product was obtained. The crude product was further purified by column chromatography to obtain 0.6 g of compound 273, with a yield of 91%. LC-MS confirmed the compound as the target product with a molecular weight of 1136.5.

[0202] Synthetic Example 17: Synthesis of Compound 282

[0203] Step 1: Synthesis of iridium dimer [ka] A mixture of intermediate 36 (1.77 g, 3.87 mmol), iridium trichloride trihydrate (390 mg, 1.11 mmol), 2-ethoxyethanol (24 mL), and water (8 mL) was refluxed under nitrogen for 24 hours. After cooling to room temperature, the iridium dimer was obtained as a red solid by filtration. It was used directly in the next reaction without further purification.

[0204] Step 2: Synthesis of Compound 282 [ka] The iridium dimer obtained in the above step, 3,7-diethyl-3,7-dimethylnonane-4,6-dione (0.4 g, 1.66 mmol), and potassium carbonate (0.77 g, 5.6 mmol) were added to a 100 mL round-bottom flask and reacted at 50 °C for 48 hours under nitrogen gas protection. The mixture was then poured into a diatomaceous earth funnel, filtered, and washed with ethanol. Dichloromethane was added to the resulting solid, and the filtrate was collected. Ethanol was then added, and the resulting solution was concentrated, but not completely. After filtration, 0.7 g of crude product was obtained. The crude product was further purified by column chromatography to obtain 0.25 g of compound 282, a 17% yield. LC-MS confirmed that the compound was the target product with a molecular weight of 1344.6.

[0205] Synthetic Example 18: Synthesis of Compound 287

[0206] Step 1: Synthesis of compound 287 [ka] Iridium dimer (0.94 g, 0.45 mmol), 3,7-diethyl-3,7-dimethylnonane-4,6-dione (0.32 g, 1.34 mmol), and potassium carbonate (0.62 g, 4.45 mmol) were dissolved in 25 mL of ethoxyethanol and reacted at 40 °C for 24 hours under nitrogen gas protection. The mixture was then poured into a funnel containing diatomaceous earth, filtered, and washed with ethanol. Dichloromethane was added to the resulting solid, and the filtrate was collected. Ethanol was then added, and the resulting solution was concentrated, but not completely. After filtration, 0.87 g of compound 287 was obtained, representing a 78% yield. LC-MS confirmed this compound to be the target product with a molecular weight of 1248.6.

[0207] Synthetic Example 19: Synthesis of Compound 291

[0208] Step 1: Synthesis of intermediate 38 [ka] Intermediate 37 (2.68 g, 8.69 mmol) and TMEDA (1.31 g, 11.3 mmol) were dissolved in 80 mL of ultra-dry THF. The reaction mixture was cooled to 0 °C and n-butyllithium (4.2 mL, 10.43 mmol, 2.5 M) was slowly added. After reacting at this temperature for 1 h, pinacol isopropoxyboronate (2.102 g, 11.3 mmol) was added and the mixture was allowed to react overnight. After TLC showed the reaction was complete, the reaction was quenched by adding saturated ammonium chloride, extracted with EA, dried, filtered, and rotary evaporated to remove the solvent to give the crude product. Purification by silica gel column chromatography gave Intermediate 38 (3.86 g, 82%).

[0209] Step 2: Synthesis of intermediate 39 [ka] A mixture of intermediate 12 (1.95 g, 8.4 mmol), intermediate 38 (3.85 g, 8.4 mmol), Pd(PPh3)4 (0.48 g, 0.42 mmol), sodium carbonate (1.34 g, 12.6 mmol), and 1,4-dioxane / water (32 mL / 8 mL) was heated to reflux under nitrogen gas protection and reacted overnight. After TLC showed the reaction was complete, the mixture was cooled to room temperature. Water was added to the reaction mixture, and the organic phase was extracted with EA, dried, filtered, and rotary evaporated to remove the solvent to give intermediate 39 (3.1 g, 70% yield).

[0210] Step 3: Synthesis of intermediate 40 [ka] Intermediate 39 (3.1 g, 5.91 mmol) was dissolved in 15 mL of ethanol, and 15 mL of 2N HCl was slowly added to the reaction mixture. The mixture was then heated to reflux and reacted for 2 h. After TLC showed the reaction was complete, the mixture was cooled to room temperature, neutralized with sodium bicarbonate solution, and filtered to obtain a crude solid. The crude solid was purified by column chromatography to obtain Intermediate 40 (2.75 g, 99.78% yield).

[0211] Step 4: Synthesis of intermediate 41 [ka] Intermediate 40 (2.75 g, 5.9 mmol), cuprous bromide (86 mg, 0.6 mmol), 2,2,6,6-tetramethylheptanedione (0.88 g, 4.8 mmol), cesium carbonate (4.89 g, 15 mmol), and DMF (60 mL) were heated to 135 °C under nitrogen gas protection and reacted overnight. After TLC showed the reaction was complete, the mixture was cooled to room temperature. Water was added until a large amount of yellow solid precipitated in the solution. After filtration, the solid was washed with water several times and then pumped to dryness to give Intermediate 41 (2.54 g, 99.8% yield) as a yellow solid.

[0212] Step 5: Synthesis of intermediate 42 [ka] Intermediate 41 (2.54 g, 5.91 mmol), neopentylboronic acid (1.37 g, 11.83 mmol), Pd(dba) (135 mg, 0.15 mmol), Sphos (243 mg, 0.59 mmol), KPO.3HO (4.72 g, 17.7 mmol), and 30 mL of toluene were combined. The reaction was evacuated and flushed with nitrogen three times, heated to reflux, and allowed to react overnight. After completion of the reaction as determined by TLC, the mixture was cooled to room temperature and rotary evaporated to remove the solvent, affording the crude product. Purification by column chromatography afforded intermediate 42 (1.8 g, 65% yield).

[0213] Step 6: Synthesis of the iridium dimer [ka] A mixture of intermediate 42 (1.4 g, 3.0 mmol), iridium trichloride trihydrate (0.35 g, 1.0 mmol), 2-ethoxyethanol (12 mL), and water (4 mL) was refluxed under nitrogen for 24 hours. After cooling to room temperature, the iridium dimer was obtained as a red solid by filtration. It was used directly in the next reaction without further purification.

[0214] Step 7: Synthesis of Compound 291 [ka] The iridium dimer obtained in the above step, 3,7-diethyl-1,1,1-trifluorononane-4,6-dione (0.39 g, 1.5 mmol), and potassium carbonate (0.69 g, 5.00 mmol) were dissolved in 16 mL of ethoxyethanol and reacted at 50 °C for 24 hours under nitrogen gas protection. The mixture was then poured into a diatomaceous earth funnel, filtered, and washed with ethanol. Dichloromethane was added to the resulting solid, and the filtrate was collected. Ethanol was then added, and the resulting solution was concentrated, but not completely. After filtration, 0.71 g of compound 291 was obtained, with a yield of 41.2%. LC-MS confirmed this compound as the target product with a molecular weight of 1386.7.

[0215] Synthetic Example 20: Synthesis of Compound 292

[0216] Step 1: Synthesis of iridium dimer [ka] A mixture of intermediate 43 (1.4 g, 2.92 mmol), iridium trichloride trihydrate (0.34 g, 0.97 mmol), 2-ethoxyethanol (12 mL), and water (4 mL) was refluxed under nitrogen for 24 hours. After cooling to room temperature, the iridium dimer was obtained as a red solid by filtration. It was used directly in the next reaction without further purification.

[0217] Step 2: Synthesis of Compound 292 [ka] The iridium dimer obtained in the above step, 3,7-diethyl-1,1,1-trifluorononane-4,6-dione (0.38 g, 1.5 mmol), and potassium carbonate (0.67 g, 4.85 mmol) were dissolved in 16 mL of ethoxyethanol and reacted at 50 °C for 24 hours under nitrogen gas protection. The mixture was then poured into a diatomaceous earth funnel, filtered, and washed with ethanol. Dichloromethane was added to the resulting solid, and the filtrate was collected. Ethanol was then added, and the resulting solution was concentrated, but not completely. After filtration, 0.67 g of compound 292 was obtained, with a yield of 49%. LC-MS confirmed this compound to be the target product with a molecular weight of 1414.7.

[0218] Synthetic Example 21: Synthesis of Compound 293

[0219] Step 1: Synthesis of compound 293 [ka] Iridium dimer (1.01 g, 0.97 mmol), 3,3,7-triethylnonane-4,6-dione (0.4 g, 1.5 mmol), and potassium carbonate (0.72 g, 4.85 mmol) were dissolved in 16 mL of ethoxyethanol and reacted at 50 °C for 24 hours under nitrogen gas protection. The mixture was then poured into a funnel containing diatomaceous earth, filtered, and washed with ethanol. Dichloromethane was added to the resulting solid, and the filtrate was collected. Ethanol was then added, and the resulting solution was concentrated, but not completely. After filtration, 0.62 g of compound 293 was obtained, representing a 45% yield. LC-MS confirmed this compound to be the target product with a molecular weight of 1388.8.

[0220] Synthetic Example 22: Synthesis of Compound 294

[0221] Step 1: Synthesis of iridium dimer [ka] A mixture of intermediate 44 (0.68 g, 1.60 mmol), iridium trichloride trihydrate (0.16 g, 0.45 mmol), 2-ethoxyethanol (6 mL), and water (2 mL) was refluxed under nitrogen for 24 hours. After cooling to room temperature, the iridium dimer was obtained as a red solid by filtration. It was used directly in the next reaction without further purification.

[0222] Step 2: Synthesis of compound 294 [ka] The iridium dimer obtained in the above step, 3,7-diethyl-3,7-dimethylnonane-4,6-dione (0.22 g, 0.9 mmol), and potassium carbonate (0.62 g, 4.5 mmol) were dissolved in 16 mL of ethoxyethanol and reacted at 50 °C for 24 hours under nitrogen gas protection. The mixture was then poured into a diatomaceous earth funnel, filtered, and washed with ethanol. Dichloromethane was added to the resulting solid, and the filtrate was collected. Ethanol was then added, and the resulting solution was concentrated, but not completely. After filtration, 0.42 g of compound 294 was obtained, representing a 73% yield. LC-MS confirmed this compound to be the target product with a molecular weight of 1276.7.

[0223] Synthetic Example 23: Synthesis of Compound 295

[0224] Step 1: Synthesis of iridium dimer [ka] A mixture of intermediate 45 (2.03 g, 4.93 mmol), iridium trichloride trihydrate (0.48 g, 1.37 mmol), 2-ethoxyethanol (33 mL), and water (11 mL) was refluxed under nitrogen for 24 hours. After cooling to room temperature, the iridium dimer was obtained as a red solid by filtration. It was used directly in the next reaction without further purification.

[0225] Step 2: Synthesis of Compound 295 [ka] The iridium dimer obtained in the above step, 3,7-diethyl-1,1,1-trifluorononane-4,6-dione (0.53 g, 2 mmol), and potassium carbonate (0.95 g, 6.85 mmol) were mixed with ethoxyethanol (23 mL). After purging with nitrogen gas, the mixture was allowed to react at room temperature for 48 hours. The reaction solution was filtered through diatomaceous earth, the filter cake was washed with an appropriate amount of EtOH, and the crude product was rinsed with DCM into a 250 mL eggplant-shaped flask. EtOH (approximately 10 mL) was added, and the DCM was removed by rotary evaporation at room temperature. The solid was filtered and washed with an appropriate amount of EtOH to obtain the crude product. The crude product was purified by column chromatography to obtain 0.1 g of compound 295, a 5.7% yield. LC-MS confirmed this compound as the target product with a molecular weight of 1278.5.

[0226] Synthetic Example 24: Synthesis of Compound 280

[0227] Step 1: Synthesis of iridium dimer [ka] At room temperature, intermediate 46 (0.15 g, 0.526 mmol) was dissolved in 9 mL of 2-ethoxyethanol and 3 mL of water, and IrCl3·3H2O (62 mg, 0.175 mmol) was added. The mixture was heated to 160 °C in an autoclave. Refluxed at this temperature for 24 h and then cooled to room temperature. The solid was filtered and washed with ethanol until the washings were colorless. The iridium dimer was obtained as a red solid by suction filtration. This product could be used directly in the next reaction without further purification.

[0228] Step 2: Synthesis of Compound 280 [ka] The iridium dimer (0.25 g, 0.157 mmol) obtained in the above step was placed in a 100 mL round-bottom flask, and K2CO3 (217 mg, 1.57 mmol) and 3,7-diethyl-3-methylnonane-4,6-dione (142 mg, 0.629 mmol) were added. 5 mL of 2-ethoxyethanol and 5 mL of DCM were added. The mixture was flushed with nitrogen gas three times at room temperature, heated to 40 °C, and stirred under nitrogen gas protection for 24 h. The DCM was removed in vacuo, filtered through diatomaceous earth, and the solid was washed with ethanol until the washings were colorless. The ethanol was removed by suction filtration. The red solid on the diatomaceous earth was dissolved in 200 mL of dichloromethane under vacuum suction filtration, 20 mL of ethanol was added, and the dichloromethane was removed by vacuum suction filtration, resulting in the precipitation of a solid. After filtration, a red solid, Compound 280 (195 mg, 0.20 mmol, 63.7% yield), was obtained, which was identified as the target product with a molecular weight of 986.3 by LC-MS.

[0229] Synthesis Example 25: Ligand L a1931 Synthesis of compounds containing

[0230] Step 1: Synthesis of intermediate 48 [ka] A mixture of intermediate 12 (1.63 g, 7.0 mmol), intermediate 47 (3.9 g, 7.4 mmol), Pd(PPh3)4 (0.4 g, 0.35 mmol), sodium carbonate (1.11 g, 10.5 mmol), and 1,4-dioxane / water (28 mL / 7 mL) was heated to reflux under nitrogen gas protection and reacted overnight. After TLC showed the reaction was complete, the mixture was cooled to room temperature. Water was added to the reaction mixture, and the organic phase was extracted with EA, dried, filtered, and rotary evaporated to remove the solvent to give intermediate 48 (3.2 g, 76% yield).

[0231] Step 2: Synthesis of intermediate 49 [ka] Intermediate 48 (3.2 g, 5.33 mmol) was dissolved in 15 mL of ethanol, and 15 mL of 2N HCl was slowly added to the reaction mixture. The mixture was then heated to reflux and reacted for 2 h. After TLC showed the reaction was complete, the mixture was cooled to room temperature, neutralized with sodium bicarbonate solution, and filtered to obtain a crude solid. The crude solid was purified by column chromatography to obtain intermediate 49 (2.65 g, 94.5% yield).

[0232] Step 3: Synthesis of intermediate 50 [ka] Intermediate 49 (2.65 g, 5.0 mmol), cuprous bromide (72 mg, 0.5 mmol), 2,2,6,6-tetramethylheptanedione (0.74 g, 4.0 mmol), cesium carbonate (4.07 g, 12.5 mmol), and DMF (50 mL) were heated to 135 °C under nitrogen gas protection and reacted overnight. After TLC showed the reaction was complete, the mixture was cooled to room temperature. Water was added until a large amount of yellow solid precipitated in the solution. After filtration, the solid was washed with water several times and then pumped to dryness to give Intermediate 50 (2.26 g, 92.4% yield) as a yellow solid.

[0233] Step 4: Synthesis of intermediate 51 [ka] Intermediate 50 (2.26 g, 4.62 mmol), neopentylboronic acid (1.07 g, 9.23 mmol), Pd(dba) (106 mg, 0.12 mmol), Sphos (190 mg, 0.46 mmol), KPO.3HO (3.69 g, 13.9 mmol), and 30 mL of toluene were combined. The reaction mixture was evacuated and flushed with nitrogen three times, heated to reflux, and allowed to react overnight. After completion of the reaction was confirmed by TLC, the mixture was cooled to room temperature and rotary evaporated to remove the solvent, yielding the crude product. Purification by column chromatography afforded intermediate 51 (1.8 g, 74% yield). The structure of this intermediate was confirmed as the target structure with a molecular weight of 525.3 by LC-MS.

[0234] From intermediate 51, a person skilled in the art can synthesize the ligand L of the present invention by referring to the methods in the prior art or the synthetic methods of Examples 1 to 24. a1931 A compound comprising:

[0235] 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.

[0236] Example of the element

[0237] Element Example 1

[0238] 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 a 1000 Å to 2000 Å hole-injection layer (HIL), the compound HI was used as a hole-injection layer (HIL) with a thickness of 100 Å. The compound HT was used as a hole-transport layer (HTL) with a thickness of 400 Å. The compound EB1 was used as an electron-blocking layer (EBL) with a thickness of 50 Å. Then, the compound 81 of the present invention was doped into the host compound RH to form an emitting layer (EML, 2:98) with a thickness of 400 Å. The compound HB was used as a hole-blocking layer (HBL) with a thickness of 50 Å. The compound ET and 8-hydroxyquinoline-lithium (Liq) were co-deposited on the HBL to form an electron-transport layer (ETL) with a thickness of 350 Å. Finally, a 1-nm thick Liq was deposited as an electron-injection layer, and a 120-nm thick Al layer was deposited as a cathode. The device was then transferred to a glove box and encapsulated with a glass cover and a moisture absorbent to complete the device.

[0239] Element Example 2

[0240] The preparation method of Device Example 2 is the same as Device Example 1, except that Compound 83 of the present invention replaces Compound 81 of the present invention in the light-emitting layer (EML).

[0241] Element Example 3

[0242] The preparation method of Device Example 3 is the same as Device Example 1, except that in the light-emitting layer (EML), Compound 81 of the present invention is replaced with Compound 64 of the present invention, the doping ratio of Compound 64 of the present invention to Compound RH is adjusted to 3:97, and Compound EB2 is replaced with Compound EB1 in the electron-blocking layer (EBL).

[0243] Element Example 4

[0244] The preparation method of Device Example 4 is the same as Device Example 3, except that Compound 93 of the present invention is substituted for Compound 64 of the present invention in the light-emitting layer (EML).

[0245] Element Example 5

[0246] The preparation method of Device Example 5 is the same as Device Example 3, except that Compound 117 of the present invention replaces Compound 64 of the present invention in the light-emitting layer (EML).

[0247] Element Example 6

[0248] The preparation method of Device Example 6 is the same as Device Example 3, except that Compound 116 of the present invention is substituted for Compound 64 of the present invention in the light-emitting layer (EML).

[0249] Device Example 7

[0250] The preparation method of Device Example 7 is the same as Device Example 3, except that Compound 261 of the present invention replaces Compound 64 of the present invention in the light-emitting layer (EML).

[0251] Device Example 8

[0252] The preparation method of Device Example 8 is the same as Device Example 3, except that Compound 262 of the present invention is substituted for Compound 64 of the present invention in the light-emitting layer (EML).

[0253] Device Example 9

[0254] The preparation method of Device Example 9 is the same as Device Example 3, except that Compound 264 of the present invention is substituted for Compound 64 of the present invention in the light-emitting layer (EML).

[0255] Device Example 10

[0256] The preparation method of Device Example 10 is the same as Device Example 3, except that Compound 263 of the present invention is substituted for Compound 64 of the present invention in the light-emitting layer (EML).

[0257] Device Example 11

[0258] The preparation method of Device Example 11 is the same as Device Example 3, except that Compound 266 of the present invention replaces Compound 64 of the present invention in the light-emitting layer (EML).

[0259] Device Example 12

[0260] The preparation method of Device Example 12 is the same as Device Example 3, except that Compound 265 of the present invention replaces Compound 64 of the present invention in the light-emitting layer (EML).

[0261] Device Example 13

[0262] The preparation method of Device Example 13 is the same as Device Example 3, except that Compound 267 of the present invention replaces Compound 64 of the present invention in the light-emitting layer (EML).

[0263] Device Example 14

[0264] The preparation method of Device Example 14 is the same as Device Example 3, except that Compound 282 of the present invention replaces Compound 64 of the present invention in the light-emitting layer (EML).

[0265] Device Example 15

[0266] The preparation method of Device Example 15 is the same as Device Example 3, except that Compound 273 of the present invention is substituted for Compound 64 of the present invention in the light-emitting layer (EML).

[0267] Device Example 16

[0268] The preparation method of Device Example 16 is the same as Device Example 3, except that Compound 294 of the present invention replaces Compound 64 of the present invention in the light-emitting layer (EML).

[0269] Device Example 17

[0270] The preparation method of Device Example 17 is the same as Device Example 3, except that Compound 287 of the present invention replaces Compound 64 of the present invention in the light-emitting layer (EML).

[0271] Device Example 18

[0272] The preparation method of Device Example 18 is the same as Device Example 3, except that Compound 291 of the present invention replaces Compound 64 of the present invention in the light-emitting layer (EML).

[0273] Device Example 19

[0274] The preparation method of Device Example 19 is the same as Device Example 3, except that Compound 292 of the present invention is substituted for Compound 64 of the present invention in the light-emitting layer (EML).

[0275] Element Example 20

[0276] The preparation method of Device Example 20 is the same as Device Example 3, except that Compound 293 of the present invention is substituted for Compound 64 of the present invention in the light-emitting layer (EML).

[0277] Device Example 21

[0278] The preparation method of Device Example 21 is the same as Device Example 3, except that Compound 295 of the present invention replaces Compound 64 of the present invention in the light-emitting layer (EML).

[0279] Comparative Example 1 of the Element

[0280] The preparation method of Comparative Example 1 of the device is the same as that of Example 1 of the device, except that Compound RD is substituted for Compound 81 of the present invention in the light-emitting layer (EML).

[0281] Comparative example 2 of the element

[0282] The preparation method of Comparative Example 2 of the device is the same as that of Example 3 of the device, except that Compound RD is substituted for Compound 64 of the present invention in the light-emitting layer (EML).

[0283] The detailed layer structure and thickness of the element are shown in the table below: Layers using more than one material are obtained by doping different compounds in the weight ratios given above.

[0284] [Table 1-1] [Table 1-2]

[0285] The structure of the material used in the element is represented as follows: [ka] [ka] [ka] [ka] [ka]

[0286] The IVL and lifetime characteristics of the devices were measured at different current densities and voltages. Table 2 shows the IVL and lifetime characteristics of the devices at 15 mA / cm 2 The CIE data of the element example 1, the element example 2, and the element comparative example 1 measured at a constant current of 1000 V, the driving voltage (V), the maximum emission wavelength (λ max ), full width at half maximum (FWHM), external quantum efficiency (EQE), and 80mA / cm 2 The figure shows the service life (LT97) at a constant current of 1000 kJ / s.

[0287] [Table 2]

[0288] summary As can be seen from the data in Table 2, the full width at half maximum in Comparative Example 1 and Examples 1 and 2 was about 30 nm, which was a very surprising level. However, while the maximum emission wavelength in Comparative Example 1 was 566 nm, in Examples 1 and 2, the design of the luminescent dopant molecular structure achieved a significant red shift in the emission wavelength, resulting in an emission wavelength of 606 nm to 620 nm, which can meet the need to emit a band different from the red. 2 At a constant current of 80 mA / cm in Comparative Example 1 and Examples 1 and 2, the voltage and external quantum efficiency data were both superior to Comparative Example 1, and in particular, the external quantum efficiency in Example 2 was 36% higher than that in Comparative Example 1. 2Regarding the service life data for LT97 at a constant current of 1000 Hz, the service life under these conditions in Comparative Example 1 is 2 hours, in Example 1 it is 30 hours, and in Example 2 it is 105 hours. As can be seen, the compound of the present invention can significantly improve the service life of an electroluminescent device. From the analysis of the above data, it can be seen that the examples not only maintain a very narrow full width at half maximum, but also effectively adjust the emission wavelength to meet the red light emission needs, reduce voltage, improve EQE, and most importantly, significantly improve the service life, thereby providing excellent performance.

[0289] Table 3 shows the 15mA / cm 2 CIE data of the device in Example 3 measured at a constant current of 1000 kJ / s, driving voltage (V), maximum emission wavelength (λ max ), full width at half maximum (FWHM) and service life (LT97) are shown.

[0290] [Table 3]

[0291] summary As can be seen from the data shown in Table 3, by adjusting the molecular structure, the emission wavelength of Example 3 was 633 nm, which was in the crimson region. 2 At a constant current of 1000 kJ / s, the full width at half maximum in Example 3 is also very narrow, 39 nm, and the driving voltage is relatively low, 3.78 V.

[0292] Table 4 shows the 15mA / cm 2 The CIE data, driving voltage (V), maximum emission wavelength (λ) of Comparative Example 2 and Examples 4 to 21 of the elements measured at a constant current of max ), full width at half maximum (FWHM), external quantum efficiency (EQE), and 80mA / cm 2 The figure shows the service life (LT97) at a constant current of 1000 kJ / s.

[0293] [Table 4]

[0294] summary Similarly, as can be seen from the device data in Table 4, in Examples 4 to 13, when the compounds of the present invention are used as the emissive layer dopants, they all successfully achieve a significant red shift in the maximum emission wavelength of the device, with the emission wavelength ranging from 614 nm to 623 nm, thereby meeting the need for emitting a band different from red. However, in Comparative Example 2, which uses Comparative Compound RD, the maximum emission wavelength is only 566 nm, which does not fully meet the need for the emission color of red light devices. Also, the current consumption of 15 mA / cm 2 At a constant current of 80 mA / cm, the full width at half maximum and voltage in Examples 4 to 13 are basically the same as or slightly inferior to those in Comparative Example 2. However, it should be noted that the full width at half maximum of less than 36 nm provided by Examples 4 to 13 is still at a very high level in the industry, while the voltage in Examples 4 to 13 is at a low level in the industry. Meanwhile, the external quantum efficiency data in Examples 4 to 13 is further improved compared to the high level in Comparative Example 2. Most importantly, the external quantum efficiency data of Examples 4 to 13 is 80 mA / cm. 2 The service life data for LT97 at a constant current of 1000 kJ / s is significantly improved (at least 20 times and at most 50 times) compared to Comparative Example 2 (the service life under these conditions is only 3 hours, which does not fully meet the needs). The above comparison once again proves that the compounds of the present invention have excellent performance.

[0295] Similarly, as can be seen from the device data in Table 4, in Examples 14 to 21, when the compounds of the present invention are used as the emissive layer dopants, they all successfully achieve a significant red shift in the maximum emission wavelength of the device, with the emission wavelength ranging from 607 nm to 625 nm, thereby meeting the need for emitting a band different from red. However, in Comparative Example 2, which uses Comparative Compound RD, the maximum emission wavelength is only 566 nm, which does not fully meet the need for the emission color of red light devices. Also, the current consumption is 15 mA / cm. 2At a constant current of 80 mA / cm, the full width at half maximum and voltage in Examples 14 to 21 are essentially the same as or slightly inferior to those in Comparative Example 2. However, the full width at half maximum of less than 36 nm provided by Examples 14 to 21 is still at a very high level within the industry, while the voltage in Examples 14 to 21 is at a low level within the industry. Meanwhile, the external quantum efficiency data in Examples 14 to 21 can be maintained close to the high level of Comparative Example 2, or even improved compared to the high level of Comparative Example 2. Most importantly, the external quantum efficiency data of Examples 14 to 21 at 80 mA / cm 2 The data of the service life of LT97 at a constant current of 1000 kJ / s is significantly improved (approaching at least 9 times and at most 50 times) compared with Comparative Example 2 (the service life under the conditions is only 3 hours, which cannot fully meet the needs). The above comparison once again proves that the compound according to the present invention has excellent performance.

[0296] Device Example 22

[0297] The preparation method of Device Example 22 was the same as Device Example 3, except that in the light-emitting layer (EML), Compound 64 of the present invention was replaced with Compound 280 of the present invention, and Compound RH2 was replaced with Compound RH.

[0298] Device Example 23

[0299] The preparation method of the device of Example 23 is the same as that of the device of Example 22, except that the weight ratio of the compound 280 of the present invention to the host compound RH2 in the light-emitting layer (EML) is adjusted to 2:98.

[0300] The detailed layer structure and thickness of the element are shown in the table below: Layers using more than one material are obtained by doping different compounds in the weight ratios given above.

[0301] [Table 5]

[0302] The structure of the new material used in the device is represented as follows: [ka]

[0303] The IVL and lifetime characteristics of the devices were measured at different current densities and voltages. Table 6 shows the IVL and lifetime characteristics of the devices at 15 mA / cm 2 CIE data for Examples 22 and 23 of the devices measured at a constant current of 1000 Hz, driving voltage (V), maximum emission wavelength (λ max ), full width at half maximum (FWHM), external quantum efficiency (EQE), and 80mA / cm 2 The figure shows the service life (LT97) at a constant current of 1000 kJ / s.

[0304] [Table 6]

[0305] As can be seen from the data in Table 6, when the compounds of the present invention are used as emissive dopants in devices, the maximum emission wavelength of the device reaches 625 nm, satisfying the need for red light emission. At the same time, the full width at half maximum of Examples 22 and 23 is less than 30 nm, a very surprising level, enabling highly saturated emission. Furthermore, the voltages of Examples 22 and 23 are both less than 3.5 V, which is very low, and the external quantum efficiency is greater than 20%, resulting in high device efficiency. Most importantly, Examples 22 and 23 have very long device life. The above data once again demonstrate the excellent performance of the compounds of the present invention.

[0306] In summary, the compound of the present invention can effectively adjust the emission wavelength to meet the red light emission needs, reduce the voltage or maintain a low voltage level, improve the EQE, and most importantly, significantly improve the service life, thereby providing excellent performance.

[0307] Research on OLED red light-emitting materials has shown that in the structure represented by Formula 1, when the substituent R is not a hydrogen atom, the emission spectrum of the material can be well adjusted and the external quantum efficiency of the material can be improved. [ka]

[0308] However, repeated studies have shown that ligands having the structure of Formula 2 are not successful in complexing with metals to form metal complexes. [ka]

[0309] Surprisingly, by structural design, the substituent R in Formula 1 can be designed as part of a polycyclic ring, and have a ligand of the corresponding structure. As shown in Formula 1 of the present invention, it can be successfully combined with a metal to form a metal complex. Meanwhile, as can be seen from device research results of related compounds, when used as a light-emitting material in an electroluminescent device, the metal complexes of this structure of the present invention all exhibit excellent device performance, can effectively adjust the emission wavelength to meet the red light emission needs, obtain a very narrow full width at half maximum, reduce or maintain a low voltage, improve EQE, and most importantly, can significantly improve the service life. As a result, the uniqueness and importance of the present invention can be more prominently demonstrated.

[0310] 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. Ligand L having a structure represented by formula 1 ａ A display comprising a metal complex, comprising: 【Chemistry 1】 (Ring A and Ring B are each independently selected from a 5-membered unsaturated carbocyclic ring, an aromatic ring having 6 to 30 carbon atoms, or a heteroaromatic ring having 3 to 30 carbon atoms; R ｉ are the same or different at each occurrence and represent mono-, multi- or no substitution; R ｉｉ are the same or different at each occurrence and represent mono-, multi- or no substitution; Y is SiR ｙ R ｙ , GeR ｙ R ｙ , N.R. ｙ , P.R. ｙ , O, S or Se; Two R's ｙ When two R ｙ may be the same or different, X １ ~X ２ is the same or different for each occurrence ｘ or N, R, R ｉ , R ｉｉ , R ｘ and R ｙ 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 unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 2 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 2 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 3 to 20 ring ... 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 cyano group, an isocyano group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituents R ｉ , R ｘ , R ｙ , R and R ｉｉ may be bonded to form a ring, The metal is selected from metals with a relative atomic mass greater than 40.

2. Ring A and / or ring B are each independently selected from a 5-membered unsaturated carbocyclic ring, an aromatic ring having 6 to 18 carbon atoms, or a heteroaromatic ring having 3 to 18 carbon atoms; The display of claim 1, wherein ring A and / or ring B are each independently selected from a 5-membered unsaturated carbocyclic ring, an aromatic ring having 6 to 10 carbon atoms, or a heteroaromatic ring having 3 to 10 carbon atoms.

3. Said L ａ The display according to claim 1 or 2, wherein is selected from the structures represented by any one of formulas 2 to 19 and formulas 22 to 23. 【Chemistry 2-1】 【Chemistry 2-2】 (In Formulas 2 to 19 and Formulas 22 to 23, X １ ~X ２ is the same or different for each occurrence ｘ or N, and X ３ ~X ７ is the same or different for each occurrence ｉ or N, and A １ ~A ６ is the same or different for each occurrence ｉｉ or N, Z may be the same or different for each occurrence. ｉｉｉ R ｉｉｉ , SiR ｉｉｉ R ｉｉｉ , P.R. ｉｉｉ , O, S or NR ｉｉｉ Selected from two R ｉｉｉ When two R ｉｉｉ are the same or different, Y is SiR ｙ R ｙ , N.R. ｙ , P.R. ｙ , O, S or Se, and two R ｙ When two R ｙ are the same or different, R, R ｘ , R ｙ , R ｉ , R ｉｉ and R ｉｉｉ 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 unsubstituted 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 cyano group, an isocyano group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituents R and R ｘ , R ｙ , R ｉ , R ｉｉ and R ｉｉｉ may be bonded to form a ring, Preferably, L ａ is selected from the structures represented by formula 2, formula 9, formula 11, or formula 12, More preferably, L ａ is selected from the structure represented by formula 2.

4. In Formulas 2 to 19 and Formulas 22 to 23, X １ ~X ｎ and / or A １ ~A ｍ At least one of the X is selected from N, ｎ is the X １ ~X ７ corresponds to the largest number in any one of formulas 2 to 19 and formulas 22 to 23, ｍ is the above-mentioned A １ ~A ６ corresponds to the largest number in any one of formulas 2 to 19 and formulas 22 to 23, Preferably, in Formulas 2 to 19 and Formulas 22 to 23, X １ ~X ｎ At least one of the X is selected from N, ｎ is the X １ ~X ７ corresponds to the largest number in any one of formulas 2 to 19 and formulas 22 to 23, More preferably, X ２ 4. The display of claim 3, wherein: is N.

5. In Formulas 2 to 19 and Formulas 22 to 23, X １ ~X ２ are each independently CR ｘ Selected from X ３ ~X ７ are each independently CR ｉ Selected from A １ ~A ６ are each independently CR ｉｉ and adjacent substituents R ｘ , R ｉ , R ｉｉ may be bonded to form a ring, Preferably, the R ｘ , R ｉ , R ｉｉ are, each occurrence the same or different, 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, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a cyano group, and combinations thereof; More preferably, the R ｘ , R ｉ , R ｉｉ and wherein at least two or three of each occurrence are the same or different and are selected from the group consisting of 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, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a cyano group, and combinations thereof.

6. In Formulas 2 to 11 and Formulas 22 to 23, X ４ and / or X ５ is CR ｉ In formulas 12 to 19, X ３ is CR ｉ Selected from And the R ｉ are, each occurrence the same or different, 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, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a cyano group, or a combination thereof; Preferably, the R ｉ and each occurrence is the same or different and is selected from the group consisting of hydrogen, deuterium, fluorine, methyl, ethyl, isopropyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, norbornyl, adamantyl, trimethylsilyl, isopropyldimethylsilyl, phenyldimethylsilyl, trifluoromethyl, cyano, phenyl, and combinations thereof.

7. In Formulas 2 to 19 and Formulas 22 to 23, R is 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, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, or a combination thereof; The display according to any one of claims 3 to 6, wherein R is preferably selected from the group consisting of hydrogen, deuterium, fluorine, a methyl group, an ethyl group, an isopropyl group, an isobutyl group, a tert-butyl group, a cyclopentyl group, a cyclopentylmethyl group, a cyclohexyl group, a neopentyl group, a deuterated methyl group, a deuterated ethyl group, a deuterated isopropyl group, a deuterated isobutyl group, a deuterated tert-butyl group, a deuterated cyclopentyl group, a deuterated cyclopentylmethyl group, a deuterated cyclohexyl group, a deuterated neopentyl group, a trimethylsilyl group, or a combination thereof.

8. The display according to any one of claims 3 to 7, wherein in formulae 2 to 19 and formulae 22 to 23, Y is selected from O or S, and preferably Y is O.

9. In Formulas 2 to 19 and Formulas 22 to 23, X １ and X ２ are each independently CR ｘ Selected from Preferably, the R ｘ and each occurrence is the same or different and is 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, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, or a combination thereof.

10. In Formulas 2 to 19 and Formulas 22 to 23, X １ is CR ｘ Selected from X ２ is N, Preferably, the R ｘ is 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, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, or a combination thereof.

11. The ligand L ａ The display of any one of claims 1 to 10, wherein the compound has a structure represented by formula 20 or 21: 【Transformation 3】 (In Formula 20 and Formula 21, Y is selected from O or S; R ｘ１ , R ｘ２ , R ｉ１ , R ｉ２ , R ｉ３ , R ｉｉ１ , R ｉｉ２ , R ｉｉ３ , R ｉｉ４ 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 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 combinations thereof; R, at each occurrence, may be the same or different and is 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, 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, and combinations thereof; Preferably, R ｘ１ , R ｘ２ , R ｉ１ , R ｉ２ , R ｉ３ and / or R ｉｉ１ , R ｉｉ２ , R ｉｉ３ , R ｉｉ４ at least one or two of, each occurrence, are the same or different and are selected from the group consisting of deuterium, halogen, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group of 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group of 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group of 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group of 6 to 20 carbon atoms, or a combination thereof; R is selected from halogen, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group of 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group of 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group of 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group of 6 to 20 carbon atoms, or a combination thereof; More preferably, R ｘ１ , R ｘ２ , R ｉ１ , R ｉ２ , R ｉ３ and / or R ｉｉ１ , R ｉｉ２ , R ｉｉ３ , R ｉｉ４ and at least one or two of R, which may be the same or different at each occurrence, are selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, or a combination thereof; and R is selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, 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, or a combination thereof.

12. R ｉ２ is selected from the group consisting of 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, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, or a combination thereof; R is selected from the group consisting of a halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted 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, or a combination thereof; R ｉｉ１ , R ｉｉ２ , R ｉｉ３ , R ｉｉ４ at least one or two of, each occurrence, are 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 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, or a combination thereof; Preferably, R ｉ２ is selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, or a combination thereof; R is selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, or a combination thereof; R ｉｉ１ , R ｉｉ２ , R ｉｉ３ , R ｉｉ４ and at least one or two of, at each occurrence, are the same or different and are selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, or a combination thereof.

13. In Formula 20 and Formula 21, R ｘ１ , R ｘ２ , R ｉ１ , R ｉ２ , R ｉ３ , R ｉｉ１ , R ｉｉ２ , R ｉｉ３ , R ｉｉ４ at least one of R, each occurrence of which may be the same or different, is selected from the group consisting of a substituted or unsubstituted alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, and combinations thereof; Preferably, R ｘ１ , R ｘ２ , R ｉ１ , R ｉ２ , R ｉ３ , R ｉｉ１ , R ｉｉ２ , R ｉｉ３ , R ｉｉ４ 13. The display of claim 11 or 12, wherein at least one of R, each occurring identically or differently, is selected from the group consisting of a substituted or unsubstituted alkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, and combinations thereof.

14. L ａ A display according to any one of claims 1 to 13, wherein each occurrence is the same or different and is selected from the group consisting of the following structures: 【Chemistry 4-1】 【Chemistry 4-2】 【Chemistry 4-3】 【Chemistry 4-4】 [Chemistry 4-5] [Chemistry 4-6] 【Chemistry 4-7】 【Chemistry 4-8】 【Chemistry 4-9】 【Chemistry 4-10】 【Chemistry 4-11】 【Chemistry 4-12】 【Chemistry 4-13】 【Chemistry 4-14】 【Chemistry 4-15】 【Chemistry 4-16】 【Chemistry 4-17】 【Chemistry 4-18】 【Chemistry 4-19】 【Chemistry 4-20】 【Chemistry 4-21】 【Chemistry 4-22】 【Chemistry 4-23】 【Chemistry 4-24】 【Chemistry 4-25】 【Chemistry 4-26】 【Chemistry 4-27】 【Chemistry 4-28】 [Chemistry 4-29] 【Chemistry 4-30】 【Chemistry 4-31】 【Chemistry 4-32】 【Chemistry 4-33】 【Chemistry 4-34】 【Chemistry 4-35】 【Chemistry 4-36】 【Chemistry 4-37】 【Chemistry 4-38】 【Chemistry 4-39】 【Chemistry 4-40】 【Chemistry 4-41】 【Chemistry 4-42】 【Chemistry 4-43】 【Chemistry 4-44】 【Chemistry 4-45】 [Chemistry 4-46] 【Chemistry 4-47】 【Chemistry 4-48】 [Chemistry 4-49] 【Chemistry 4-50】 【Chemistry 4-51】 【Chemistry 4-52】 [Chemistry 4-53] [Chemistry 4-54] 【Chemistry 4-55】 [Chemistry 4-56] 【Chemistry 4-57】 [Chemistry 4-58] [Chemistry 4-59] 【Chemistry 4-60】 【Chemistry 4-61】 【Chemistry 4-62】 (In the above structure, TMS is a trimethylsilyl group, The hydrogen atoms in the above structure may be partially or completely replaced with deuterium atoms.

15. The metal complex is M(L ａ ) ｍ (L ｂ ) ｎ (L ｃ ) ｑ having the structure the metal M is chosen from metals with a relative atomic mass greater than 40; L ａ , L ｂ and L ｃ are the first, second and third ligands of the complex, respectively; m is 1, 2 or 3, n is 0, 1 or 2, q is 0, 1 or 2, and m+n+q is equal to the oxidation state of the metal M; If m is greater than 1, multiple L ａ are the same or different, and when n is 2, two L ｂ are the same or different, and when q is 2, two L ｃ are the same or different, L ａ , L ｂ and L ｃ may be linked to form a multidentate ligand; L ｂ and L ｃ A display according to any one of claims 1 to 14, wherein each occurrence is the same or different and is selected from the group consisting of the following structures: 【Transformation 5】 (R ａ , R ｂ and R ｃ are the same or different at each occurrence and represent mono-, multi- or no substitution; X ｂ are the same or different for each occurrence and are O, S, Se, NR Ｎ１ and C.R. Ｃ１ R Ｃ２ selected from the group consisting of X ｃ and X ｄ are O, S, Se and NR, which may be the same or different at 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 unsubstituted 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 cyano group, an isocyano group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituents R ａ , R ｂ , R ｃ , R Ｎ１ , R Ｎ２ , R Ｃ１ and R Ｃ２ may be bonded to form a ring.)

16. the metal M is selected from Ir, Rh, Re, Os, Pt, Au or Cu; Preferably, the metal M is selected from Ir, Pt or Os, More preferably, the metal M is Ir.

17. L ｂ 17. The display of claim 15 or 16, wherein each occurrence is the same or different and is selected from the following structures: 【Transformation 6】 (R １ ~R ７ 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 unsubstituted 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 cyano group, an isocyano group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Preferably, R １ ~R ３ at least one or two of R are selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, or a combination thereof; and / or R ４ ~R ６ at least one of is 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, or a combination thereof; More preferably, R １ ~R ３ at least two of R are selected from a substituted or unsubstituted alkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 20 carbon atoms, or a combination thereof; and / or R ４ ~R ６ At least two of are selected from a substituted or unsubstituted alkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 20 carbon atoms, or a combination thereof.

18. L ｂ A display according to any one of claims 15 to 17, wherein each occurrence is the same or different and is selected from the group consisting of the following structures: 【Chemistry 7-1】 【Chemistry 7-2】 【Transformation 7-3】 【Chemistry 7-4】 【Transformation 7-5】 【Transformation 7-6】 【Transformation 7-7】 (L ｃ is the same or different at each occurrence and is selected from the group consisting of the following structures: 【Chemistry 8-1】 【Chemistry 8-2】 【Chemistry 8-3】 【Chemistry 8-4】 【Chemistry 8-5】 【Chemistry 8-6】

19. The metal complex is Ir(L ａ ) ２ (L ｂ ) or Ir(L ａ ) ２ (L ｃ ) or Ir(L ａ ) (L ｃ ) ２ having the structure The metal complex is Ir(L ａ ) ２ (L ｂ ) structure, L ａ may be the same or different for each occurrence of L ａ１ ~L ａ１９３１ and L ｂ Is, L ｂ１ ~L ｂ３２２ Any one selected from the group consisting of: The metal complex is Ir(L ａ ) ２ (L ｃ ) structure, L ａ may be the same or different for each occurrence of L ａ１ ~L ａ１９３１ and L ｃ Is, L ｃ１ ~L ｃ２３１ Any one selected from the group consisting of: The metal complex is Ir(L ａ ) (L ｃ ) ２ When L has the structure ａ Is, L ａ１ ~L ａ１９３１ and L is any one selected from the group consisting of ｃ may be the same or different for each occurrence of L ｃ１ ~L ｃ２３１ Any one or two selected from the group consisting of: The display of claim 18, wherein the metal complex is preferably selected from the group consisting of Compound 1 to Compound 312. (The compounds 1 to 200 and compounds 261 to 312 are Ir(L ａ ) ２ (L ｂ ) structure, and two L ａ are identical, and L ａ and L ｂ are each correspondingly selected from the structures listed in the table below, Table 1-1 Table 1-2 Table 1-3 Table 1-4 Table 1-5 Compounds 201 to 260 are Ir(L ａ ) ２ (L ｂ ) structure, and two L ａ are different, L ａ and L ｂ are each selected from the structures listed in the table below. Table 2-1 Table 2-2

20. Ligand L having a structure represented by formula 1 ａ 1. An illumination lamp comprising a metal complex, comprising: 【Chemistry 9】 (Ring A and Ring B are each independently selected from a 5-membered unsaturated carbocyclic ring, an aromatic ring having 6 to 30 carbon atoms, or a heteroaromatic ring having 3 to 30 carbon atoms; R ｉ are the same or different at each occurrence and represent mono-, multi- or no substitution; R ｉｉ are the same or different at each occurrence and represent mono-, multi- or no substitution; Y is SiR ｙ R ｙ , GeR ｙ R ｙ , N.R. ｙ , P.R. ｙ , O, S or Se; Two R's ｙ When two R ｙ may be the same or different, X １ ~X ２ is the same or different for each occurrence ｘ or N, R, R ｉ , R ｉｉ , R ｘ and R ｙ 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 unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 2 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 2 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 3 to 20 ring ... 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 cyano group, an isocyano group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituents R ｉ , R ｘ , R ｙ , R and R ｉｉ may be bonded to form a ring, The metal is selected from metals with a relative atomic mass greater than 40.

21. A consumer product comprising a display according to any one of claims 1 to 19 or an illumination lamp according to claim 20.

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