Organic light-emitting material containing cyano-substituted ligand

Abstract

SOLUTION: To provide a metal complex containing a cyano-substituted ligand represented by the following formula, which can be used as a light-emitting material in a light-emitting layer of an organic electroluminescent device, and to further provide an electroluminescent device containing the metal complex, a compound formulation, and a compound for preparing the metal complex.EFFECT: These novel complexes can provide better device performance, such as a narrower full width at half maximum, lower voltage values, and higher quantum efficiency.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] The present invention relates to compounds for use in organic electronic devices, such as organic light-emitting devices, and in particular to metal complexes containing cyano-substituted ligands, and electroluminescent devices and compound formulations comprising such 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 for 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] Cyano group substitution has not always been introduced into phosphorescent metal complexes, such as iridium complexes. US20140252333A1 discloses a series of cyano-phenyl-substituted iridium complexes, but the effect of the cyano group is not clearly demonstrated. Furthermore, for example, US20040121184A1 discloses that the cyano group, a highly electron-absorbing substituent, may be used to blue-shift the emission spectrum of phosphorescent metal complexes. The present invention discloses a series of novel cyano-substituted metal complexes that unexpectedly exhibit many properties, including high efficiency, low voltage, and no obvious blue-shifted or red-shifted emission. Most unexpectedly, they have a very narrow emission peak width. These advantages significantly contribute to improving the level of green light and complexion saturation. Summary of the Invention

[0009] The present invention aims to provide a series of technical solutions to solve at least some of the above-mentioned problems.

[0010] The present invention relates to a ligand L represented by formula 1. a It is an object of the present invention to provide a metal complex comprising: [ka] formula 1 (Cy is a substituted or unsubstituted aryl or heteroaryl group having 5 to 24 ring atoms; Cy is bound to the metal by a metal-carbon bond or a metal-nitrogen bond; X1 to X4 are each independently C, CR x1 or N, and at least one of X1 to X4 is C, which binds to Cy; and X1 to X4 include a plurality of CR x1 If present, the R x1 may be the same or different, X5 to X8 are each independently CR x2 Or selected from N, multiple CRs in X5 to X8 x2 If present, the R x2 may be the same or different, X is O, S, Se, or NR x3 , C.R. x4 R x5 and SiR x6 R x7 selected from the group consisting of R x1 , R x2 , R x3 , R x4 , R x5 , R x6 and R x7are each independently 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 selected from the group consisting of unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amine groups, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, thioalkyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof, R x1 and R x2 at least one of is a cyano group, two adjacent substituents may be bonded to form a ring; X1, X2, X3 or X4 is bonded to the metal by a metal-carbon bond or a metal-nitrogen bond.

[0011] A second object of the present invention is to provide an electroluminescent device comprising an anode, a cathode, and an organic layer provided between the anode and the cathode, wherein the organic layer contains the metal complex according to the first object.

[0012] A third object of the present invention is to provide a formulation for a compound containing the metal complex described in the first object.

[0013] A fourth object of the present invention is to provide a compound for preparing the metal complex described in the first object.

[0014] The novel metal complexes containing cyano-substituted ligands according to the present invention may be used as light-emitting materials in electroluminescent devices. These novel compounds can be used in electroluminescent devices to provide better device performance, such as narrower full width at half maximum, lower voltage values, and higher quantum efficiency. [Brief explanation of the drawings]

[0015] [Figure 1] 1 is a schematic diagram of an organic light-emitting device that may include metal complex and compound formulations according to the present invention. [Figure 2] 1 is a schematic diagram of another organic light emitting device that may include metal complex and compound formulations according to the present invention. [Figure 3] FIG. 1 shows the inclusion of a ligand La represented by formula 1 according to the present invention. DETAILED DESCRIPTION OF THE INVENTION

[0016] 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.

[0017] 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.

[0018] 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.

[0019] 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.

[0020] 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.

[0021] 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.

[0022] The materials and structures described herein may also be used in the other organic electronic devices listed above.

[0023] "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, various organic layers may be present between the cathode and anode, and the cathode may still be described as being "on" the anode.

[0024] "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.

[0025] 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.

[0026] 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).

[0027] 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.

[0028] 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).

[0029] Definitions of Substituent Terminology

[0030] Halogen or halide, as used herein, includes fluorine, chloro, bromine and iodine.

[0031] The alkyl group includes straight-chain and branched-chain alkyl groups. Specific examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, and 3-methylpentyl. The alkyl group may also be substituted. Carbon atoms in the alkyl group chain may be replaced with other heteroatoms. Among these, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, and neopentyl are preferred.

[0032] 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.

[0033] 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.

[0034] 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.

[0035] 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, fluorenyl, 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.

[0036] 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.

[0037] 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.

[0038] 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.

[0039] 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.

[0040] 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.

[0041] 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.

[0042] The alkyl group, cycloalkyl group, alkenyl group, alkynyl group, aralkyl group, heterocyclic group, aryl group, and heteroaryl group may be unsubstituted or may be substituted with one or more groups selected from deuterium, halogen, alkyl group, cycloalkyl group, aralkyl group, alkoxy group, aryloxy group, amino group, cyclic amino group, silyl group, alkenyl group, cycloalkenyl group, heteroalkenyl group, alkynyl group, aryl group, heteroaryl group, acyl group, carbonyl group, carboxyl group, ether group, ester group, nitrile group, isonitrile group, thioalkyl group, sulfinyl group, sulfonyl group, phosphine group, and combinations thereof.

[0043] 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.

[0044] 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.

[0045] 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 multiple available substitution positions may be the same structure or different structures.

[0046] In the compounds referred to herein, when adjacent substituents are optionally joined to form a ring, this is understood to refer to the two groups being linked to each other by a chemical bond, as illustrated by the following diagram: [ka]

[0047] Furthermore, the statement that adjacent substituents may be bonded to form a ring is understood to mean that when one of the two groups represents hydrogen, the second group is bonded to the position where the hydrogen atom is bonded to form a ring. This is exemplified by the following diagram. [ka]

[0048] According to one embodiment of the present invention, L containing a structure represented by Formula 1 a Metal complexes with ligands are disclosed. [ka] formula 1 (Cy is a substituted or unsubstituted aryl or heteroaryl group having 5 to 24 ring atoms; Cy is bound to the metal by a metal-carbon bond or a metal-nitrogen bond; X1 to X4 are each independently C, CR x1or N, and at least one of X1 to X4 is C, which binds to Cy; and X1 to X4 include a plurality of CR x1 If present, the R x1 may be the same or different, X5 to X8 are each independently CR x2 Or selected from N, multiple CRs in X5 to X8 x2 If present, the R x2 may be the same or different, X is O, S, Se, or NR x3 , C.R. x4 R x5 and SiR x6 R x7 selected from the group consisting of R x1 , R x2 , R x3 , R x4 , R x5 , R x6 and R x7 are each independently 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 selected from the group consisting of unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amine groups, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, thioalkyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof, R x1 and R x2 at least one of is a cyano group, two adjacent substituents may be bonded to form a ring; X1, X2, X3 or X4 is bonded to the metal by a metal-carbon bond or a metal-nitrogen bond. In the present specification, the phrase "two adjacent substituents may be bonded to form a ring" may include the case where any two adjacent substituents are bonded to form a ring, and may also include the case where any two adjacent substituents are not bonded to form a ring.

[0049] According to one embodiment of the present invention, Cy is [ka] any structure selected from the group consisting of: R may represent a single substitution, multiple substitutions up to the highest number of available substitutions, or no substitution; when multiple R are present in any structure, said R may be the same or different; R each independently represents hydrogen, deuterium, a halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted 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 ... selected from the group consisting of unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amine groups, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, thioalkyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof, two adjacent substituents may be bonded to form a ring; "#" represents the position bonded to the metal M, and "*" represents the position bonded to X1, X2, X3 or X4.

[0050] According to one embodiment of the present invention, the metal complex has the general formula M(L a ) m (L b ) n (L c ) q and L a is a first ligand that coordinates with the metal M, and b and the L c are a second ligand and a third ligand that coordinate to the metal M, respectively, and the L b and the L c may be the same or different, Said L a , L b and L c may be linked to form a multidentate ligand; m is 1, 2 or 3, n is 0, 1 or 2, q is 0, 1 or 2, and m+n+q equals the oxidation state of M; the metal M is selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir, and Pt, preferably the metal M is selected from Pt, Os, or Ir; L a is, independently, [ka] [ka] [ka] [ka] [ka] selected from the group consisting of L a In the structure of X is O, S, Se, or NR x3 , C.R. x4 R x5 and SiR x6 R x7 selected from the group consisting of R1, R2, R3 and R4 may represent mono-, di-, tri-, tetra- or no substitution; R1, R2, R3, R4, R x3 , R x4 , R x5 , R x6 and R x7 are each independently 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 selected from the group consisting of unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amine groups, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, thioalkyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof, At least one of R3 and R4 is a cyano group; two adjacent substituents may be bonded to form a ring; L b and L c are each independently [ka] selected from the group consisting of R a , Rb , and R c may represent mono-, di-, tri-, tetra- or unsubstituted; X b are O, S, Se, and NR N1 , and C.R. C1 R C2 selected from the group consisting of R a , R b , R c , R N1 , R C1 and R C2 are each independently 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 selected from the group consisting of unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amine groups, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, thioalkyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof, Two adjacent substituents may be bonded to form a ring.

[0051] According to one embodiment of the present invention, the ligand L a In the structural formula, X is selected from O, S, or Se.

[0052] According to one embodiment of the present invention, the compound has a structure represented by any one of formulas 2 to 10. [ka] [ka] (m is 1, 2 or 3, X is selected from O, S or Se; R1, R3 and R4 may represent mono-, di-, tri-, tetra- or no substitution; R a , R b , and R c may represent mono-, di-, tri-, tetra- or unsubstituted; R1, R3, R4, R a , R b and R c are each independently 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 selected from the group consisting of unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amine groups, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, thioalkyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof, At least one of R3 and R4 is a cyano group; Two adjacent substituents may be bonded to form a ring.

[0053] According to one embodiment of the present invention, the metal complex has a structure represented by formula 2-a. [ka] (m is 1, 2 or 3, X is selected from O, S or Se; R3 and R4 may represent mono-, di-, tri-, tetra- or no substitution; R a , R b , and R c may represent mono-, di-, tri-, tetra- or unsubstituted; R 11 , R 12 , R 13 , R 14 , R3, R4, R a , and R b are each independently 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 selected from the group consisting of unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amine groups, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, thioalkyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof, At least one of R3 and R4 is a cyano group; Two adjacent substituents may be bonded to form a ring.

[0054] According to one embodiment of the present invention, in formula 2-a, R 11 and R 14 If at least one of is not hydrogen, then R 12 and R 13are each independently 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 The alkyl group is selected from the group consisting of a substituted 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 thioalkyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

[0055] According to one embodiment of the present invention, in formula 2-a, R 11 and R 14 If both are hydrogen, R 12 and R 13 are each independently 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 heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 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 thioalkyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; and R 12 and R 13 The sum of the numbers of carbon atoms in

[0056] According to one embodiment of the present invention, in the formula 1, at least one of X5 to X8 is CR x2 and the R x2 is a cyano group.

[0057] According to one embodiment of the present invention, in the formula 1, X5 to X8 are each independently CR x2 and wherein R x2 At least one of the groups is a cyano group.

[0058] According to one embodiment of the present invention, R4 may represent mono-, di-, tri- or tetra-substitution, and when there are multiple R4, they may be the same or different, and R4 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 cyano group, and combinations thereof, and at least one of R4 is a cyano group.

[0059] According to one embodiment of the present invention, the ligand L a L a1 ~L a575 L a1 ~L a575 For the specific structure, please refer to claim 8.

[0060] According to one embodiment of the present invention, the ligand L a L a1 ~L a957 L a1 ~L a957 For the specific structure, please refer to claim 8.

[0061] According to one embodiment of the present invention, L a The hydrogen atoms in may be partially or completely deuterated.

[0062] According to one embodiment of the present invention, L a The hydrogen atoms in the aryl group may be partially or completely deuterated.

[0063] According to one embodiment of the present invention, L aThe hydrogen atoms in the alkyl group may be partially or completely deuterated.

[0064] According to one embodiment of the present invention, L a The hydrogen atoms in the ligand L may be partially or completely deuterated. a L a958 ~L a1019 and L a958 ~L a1019 For the specific structure, please refer to claim 9.

[0065] According to one embodiment of the present invention, the metal complex has the formula IrL a (L b )2 or Ir(L a )2L b L a L a1 ~L a575 One or two selected from L b L b1 ~L b41 and L b1 ~L b41 For the specific structure, please refer to claim 10.

[0066] According to one embodiment of the present invention, the metal complex has the formula IrL a (L b )2 or Ir(L a )2L b L a L a1 ~L a1019 One or two selected from L b teeth, [ka] [ka] [ka] The compound is one or two selected from the group consisting of:

[0067] According to one embodiment of the present invention, the metal complex has the formula Ir(L a )2L c , or IrL a (L c )2, and L a L a1 ~L a1019 One or two selected from L c L c1 ~L c360 Among them, L c1 ~L c360 For the specific structure, please refer to claim 11.

[0068] According to one embodiment of the present invention, the metal complex is selected from the structures represented by any one of Metal Complex 1 to Metal Complex 316, Metal complexes 1 to 226 are IrL a (L b )2 structure, and two L b are identical, and L a and L b correspond to the structures shown in the table below, [Table 1] [Table 2] [Table 3] [Table 4] Metal complexes 227 to 274 are Ir(L a )2L c It has a structure of two L a are identical, and L a and Lc correspond to the structures shown in the table below, [Table 5] [Table 6] Metal complexes 275 to 316 are Ir(L a )3 structure, and has three L a are identical, and L a corresponds to the structure shown in the table below. [Table 7]

[0069] According to one embodiment of the present invention, there is further disclosed a compound selected from the group consisting of Compound 1 to Compound 136. For specific structures of Compound 1 to Compound 136, please refer to claim 13.

[0070] According to one embodiment of the present invention, there is provided 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 represented by formula 1: a Further disclosed is an electroluminescent device comprising a metal complex comprising: [ka] formula 1 (Cy is a substituted or unsubstituted aryl or heteroaryl group having 5 to 24 ring atoms; Cy is bound to the metal by a metal-carbon bond or a metal-nitrogen bond; X1 to X4 are each independently C, CR x1 or N, and at least one of X1 to X4 is C, which binds to Cy; and X1 to X4 include a plurality of CR x1 If present, the R x1 may be the same or different, X5 to X8 are each independently CR x2 Or selected from N, multiple CRs in X5 to X8 x2 If present, the R x2 may be the same or different, X is O, S, Se, or NR x3 , C.R. x4 R x5 and SiR x6 R x7 selected from the group consisting of R x1 , R x2 , R x3 , R x4 , R x5 , R x6 and R x7 are each independently 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 selected from the group consisting of unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amine groups, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, thioalkyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof, R x1 and R x2 at least one of is a cyano group, two adjacent substituents may be bonded to form a ring; X1, X2, X3 or X4 is bonded to the metal by a metal-carbon bond or a metal-nitrogen bond.

[0071] 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.

[0072] According to an embodiment of the present invention, in the electroluminescent device, the organic layer further comprises a host material.

[0073] According to an embodiment of the present invention, in the electroluminescent device, the organic layer further comprises at least two host materials.

[0074] According to one embodiment of the present invention, the host material comprises at least one chemical group selected from the group consisting of benzene, biphenyl, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazolyl, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, azadibenzoselenophene, triphenylene, azatriphenylene, fluorenyl, silicon fluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

[0075] According to one embodiment of the invention, the electroluminescent device is integrated into a device in the group consisting of consumer products, electronic device modules, organic light emitting devices and lighting panels.

[0076] According to another embodiment of the present invention, there is further disclosed a compound formulation comprising a metal complex, the specific structure of which is represented by any one of the above-mentioned embodiments.

[0077] Combination with other materials

[0078] 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.

[0079] It is stated herein that the materials of specific layers used in organic light-emitting devices can be used in combination with various other materials present in the device. Illustratively, the light-emitting dopants disclosed herein can be used in combination with various hosts, transport layers, blocking layers, injection layers, electrodes, and other possible layers. These material combinations are described in detail in paragraphs 0080 to 0101 of patent application US2015 / 0349273A1, the contents of which are incorporated herein by reference in their entirety. The materials described or mentioned are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily refer to the literature to identify other materials that can be used in combination.

[0080] In the material synthesis examples, all reactions were carried out under nitrogen protection unless otherwise specified. All reaction solvents were anhydrous and used as obtained commercially. The synthesized products were subjected to structural confirmation and property testing using one or more instruments commonly used in the art (including, but not limited to, a Bruker nuclear magnetic resonance spectrometer, a Shimadzu liquid chromatography, a liquid chromatography / mass spectrometer, a gas chromatography / mass spectrometer, and a differential scanning calorimeter, a Shanghai Liang Optoelectronics fluorescence spectrophotometer, a Wuhan Science & Technology electrochemical workstation, and an Anhui Beike sublimation apparatus) in a manner familiar to those skilled in the art. In the device examples, the device properties were also tested using instruments commonly used in the art (including, but not limited to, an evaporator from Angstrom Engineering, an optical test system and a service life test system from Suzhou Fusida, and an ellipsometer from Beijing Liangtuo) in a manner familiar to those skilled in the art. Those skilled in the art are familiar with the relevant content, such as the use of the above-mentioned equipment and test methods, and can reliably and unaffectedly obtain specific data of the sample, so the above-mentioned relevant content will not be repeated in this specification.

[0081] Examples of material synthesis

[0082] The preparation method of the compound according to the present invention is not limited. Taking the following compounds as typical but non-limiting examples, the synthesis route and preparation method thereof are as follows:

[0083] Synthesis Example 1: Compound IrL a1 (L b1 Synthesis of )2 (metal complex 1)

[0084] Step 1: [ka] To a dry 1000 mL round-bottom flask, 3-chloro-2-methoxyphenylboronic acid (20.00 g, 107.29 mmol), 2-fluoro-3-bromobenzonitrile (20.43 g, 102.20 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) (4.39 g, 3.74 mmol), potassium carbonate (32.48 g, 235.40 mmol), 1,4-dioxane (500 mL), and water (100 mL) were added in sequence. The atmosphere was purged with N2 three times and protected with N2. The reaction mixture was placed in a heating mantle and heated under reflux with stirring for 12 h. After cooling, the reaction mixture was extracted with ethyl acetate, washed three times with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The crude product was purified by column chromatography, eluting with 5% (v / v) ethyl acetate (EA) / petroleum ether (PE) to give 22 g of a white product, Intermediate 1 (yield 74.8%).

[0085] Step 2: [ka] Intermediate 1 (22.00 g, 84.30 mmol) and dichloromethane (350 mL) were added sequentially to a dry 500 mL three-neck flask. The atmosphere was purged with N2 three times and protected with N2. The flask was placed in an ice bath at 0 °C and stirred for 5 minutes, and boron tribromide was slowly added dropwise. After the addition was complete, the mixture was allowed to warm to room temperature and reacted for 12 hours with stirring. After the reaction was complete, the mixture was quenched with ice water in an ice bath and neutralized with a saturated aqueous solution of sodium bicarbonate. A large amount of white solid product precipitated, which was directly filtered, washed with water three times, and dried under reduced pressure to obtain 19.7 g of white solid product, Intermediate 2 (yield 94.4%).

[0086] Step 3: [ka] Intermediate 2 (19.7 g, 79.6 mmol), potassium carbonate (32.9 g, 238.8 mmol), and DMF (300 mL) were added sequentially to a dry 500 mL round-bottom flask. The mixture was then placed in a heating mantle at 100 °C and stirred for 12 h. After completion of the reaction, the mixture was cooled and filtered through diatomaceous earth. The organic phase was washed with saturated brine, extracted twice with ethyl acetate, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The crude product was purified by column chromatography eluting with 20% (v / v) dichloromethane / petroleum ether to give 11 g of intermediate 3 as a white solid (60.7% yield).

[0087] Step 4: [ka] To a dry 500 mL round-bottom flask was sequentially added Intermediate 3 (9.60 g, 42.19 mmol), bis(pinacolato)diboron (13.93 g, 54.86 mmol), X-Phos (0.99 g, 2.10 mmol), palladium acetate (0.47 g, 2.10 mmol), potassium acetate (10.30 g, 105.00 mmol), and dioxane (200 mL). The mixture was purged with N2 three times, protected with N2, and heated with stirring at 100 °C overnight. After completion of the reaction, the mixture was filtered through diatomaceous earth and anhydrous magnesium sulfate, washed twice with ethyl acetate, and the organic phase was collected and concentrated under reduced pressure to give the crude product, which was used directly in the next step.

[0088] Step 5: [ka] Intermediate 4 (crude), 2-bromopyridine (6.23 g, 39.45 mmol), Pd(PPh3)4 (2.07 g, 1.79 mmol), sodium carbonate (9.49 g, 89.50 mmol), dioxane (250 mL), and water (50 mL) were added sequentially to a dry 500 mL round-bottom flask. The atmosphere was purged with N2 three times and protected with N2, and the reaction was heated at 100 °C for 12 h. After completion of the reaction, the mixture was extracted with ethyl acetate, washed with saturated brine three times, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The crude product was purified by column chromatography eluting with a gradient of PE:EA = 10:1 to 5:1 (v / v) to obtain 11.4 g of a white solid, Intermediate 5 (98% yield). Intermediate 5 was synthesized by the reaction of ligand L a The structure of the product was confirmed by NMR and GCMS.

[0089] Step 6: [ka] To a dry 500 mL round-bottom flask, intermediate 5 (3.52 g, 12.96 mmol), iridium complex (4.50 g, 6.31 mmol), and ethanol (250 mL) were added in that order. The atmosphere was purged with N2 three times and protected with N2, and the reaction was heated to reflux for 24 h. After cooling, the reaction was filtered through diatomaceous earth. The mixture was washed twice with methanol and n-hexane, and the yellow solid on the diatomaceous earth was dissolved in dichloromethane. The organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to obtain the yellow solid compound IrL. a1 (L b1 ) 2 (metal complex 1) (1.5 g, yield 28.7%) was obtained. The product was confirmed to be the target product with a molecular weight of 770.

[0090] Synthesis Example 2: Compound IrL a4 (L b1 Synthesis of )2 (metal complex 4)

[0091] Step 1: [ka] To a dry 500 mL round-bottom flask was added, in order, 6-chloro-dibenzofuran-1-nitrile (4.6 g, 20.2 mmol), bis(pinacolato)diboron (5.9 g, 23.2 mmol), palladium acetate (0.14 g, 0.6 mmol), potassium acetate (2.97 g, 30.3 mmol), X-Phos (0.58 g, 1.21 mmol), and 1,4-dioxane (90 mL). The mixture was purged with N2 three times and protected with N2, heated to reflux, and stirred overnight. After completion of the reaction, it was filtered through diatomaceous earth, anhydrous magnesium sulfate, and washed twice with ethyl acetate. The organic phase was collected and concentrated under reduced pressure to give intermediate 6, which was used directly in the next step.

[0092] Step 2: [ka] Intermediate 6 (6.4 g, 20.2 mmol), 2-bromopyridine (3.2 g, 20.2 mmol), Pd(PPh3)4 (1.4 g, 1.2 mmol), potassium carbonate (4.2 g, 30.3 mmol), 1,4-dioxane (90 mL), and water (30 mL) were added sequentially to a dry 500 mL round-bottom flask. The atmosphere was purged with N2 three times and protected with N2, and the reaction was heated at 100 °C for 12 h. After completion of the reaction, the mixture was extracted with ethyl acetate, washed with saturated brine three times, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The crude product was purified by column chromatography eluting with a gradient of PE:EA = 20:1 to 10:1 (v / v) to give 4 g of a white solid, Intermediate 7 (74% yield). Intermediate 7 was synthesized by the reaction of ligand L a The structure of the product was confirmed by NMR and GCMS.

[0093] Step 3: [ka] To a dry 500 mL round-bottom flask, intermediate 7 (2.9 g, 11.0 mmol), iridium complex (4.0 g, 5.5 mmol), and ethanol (250 mL) were added in that order. The atmosphere was purged with N2 three times and protected with N2, and the reaction was heated to reflux for 24 h. After cooling, the reaction was filtered through diatomaceous earth. The mixture was washed twice with methanol and n-hexane, and the yellow solid on the diatomaceous earth was dissolved in dichloromethane. The organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to give compound IrL, a yellow solid. a4 (L b1 ) 2 (metal complex 4) (1.5 g, 36% yield) was obtained. The structure of the product was confirmed as the target product with a molecular weight of 770.

[0094] Synthesis Example 3: Compound IrL a2 (L b1 Synthesis of )2 (metal complex 2)

[0095] Step 1: [ka] To a dry 1000 mL round-bottom flask, 3-chloro-2-methoxyphenylboronic acid (12.00 g, 64.37 mmol), 2-fluoro-3-bromobenzonitrile (12.26 g, 61.31 mmol), tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) (3.25 g, 3.05 mmol), potassium carbonate (18.61 g, 134.80 mmol), 1,4-dioxane (500 mL), and water (100 mL) were added in sequence. The atmosphere was purged with N2 three times and then protected with N2. The reaction mixture was placed in a heating mantle and heated under reflux with stirring for 12 h. After cooling, the reaction mixture was extracted with ethyl acetate, washed three times with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The crude product was purified by column chromatography, eluting with 5% (v / v) ethyl acetate (EA) / petroleum ether (PE) to give 13.2 g of a white product, Intermediate 8 (yield 82.5%).

[0096] Step 2: [ka] To a dry 500 mL three-neck flask, intermediate 8 (13.20 g, 50.50 mmol) and 350 mL of dichloromethane were added, in that order. The atmosphere was purged with N2 three times and protected with N2. The flask was placed in a 0°C ice bath and stirred for 5 minutes. Boron tribromide (19.0 g, 75.74 mmol) was then slowly added dropwise. After the addition was complete, the mixture was allowed to warm to room temperature and react for 12 hours with stirring. After completion of the reaction, the mixture was quenched with ice water in an ice bath and neutralized with a saturated aqueous solution of sodium bicarbonate. A large amount of white solid product was precipitated, which was directly filtered, washed with water three times, and dried under reduced pressure to give 11.75 g of white solid intermediate 9 (94% yield).

[0097] Step 3: [ka] Intermediate 9 (11.75 g, 47.47 mmol), potassium carbonate (19.6 g, 142.4 mmol), and DMF (300 mL) were added sequentially to a dry 500 mL round-bottom flask. The mixture was then placed in a heating mantle at 100 °C and stirred for 12 h. After completion of the reaction, the mixture was cooled and filtered through diatomaceous earth. The organic phase was washed with saturated brine, extracted twice with ethyl acetate, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The crude product was purified by column chromatography eluting with 20% (v / v) dichloromethane (DCM) / petroleum ether (PE) to give 7.09 g of a white solid, Intermediate 10 (65.7% yield).

[0098] Step 4: [ka] To a dry 500 mL round-bottom flask was added, in order, intermediate 10 (4.10 g, 18.02 mmol), bis(pinacolato)diboron (5.95 g, 23.42 mmol), X-Phos (0.43 g, 0.90 mmol), palladium acetate (0.20 g, 0.90 mmol), potassium acetate (4.46 g, 45.00 mmol), and dioxane (100 mL). The mixture was purged with N three times, protected with N, heated to 100 °C, and stirred overnight. After completion of the reaction, it was filtered through diatomaceous earth and anhydrous magnesium sulfate, washed twice with ethyl acetate, and the organic phase was collected and concentrated under reduced pressure to give crude intermediate 11, which was used directly in the next step.

[0099] Step 5: [ka] Intermediate 11 (crude), 2-bromopyridine (2.66 g, 16.85 mmol), Pd(PPh3)4 (0.88 g, 0.76 mmol), sodium carbonate (4.05 g, 38.25 mmol), dioxane (150 mL), and water (30 mL) were added sequentially to a dry 500 mL round-bottom flask. The atmosphere was purged with N2 three times and protected with N2, and the reaction was heated at 100 °C for 12 h. After completion of the reaction, the mixture was extracted with ethyl acetate, washed with saturated brine three times, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The crude product was purified by column chromatography eluting with a gradient of PE:EA = 10:1 to 5:1 (v / v) to give 4.1 g of a white solid, Intermediate 12 (90% yield). Intermediate 12 was synthesized by the reaction of ligand L a The structure of the product was confirmed by NMR and GCMS.

[0100] Step 6: [ka] To a dry 500 mL round-bottom flask, intermediate 12 (3.52 g, 12.96 mmol), iridium complex (4.50 g, 6.31 mmol), and ethanol (250 mL) were added in that order. The atmosphere was flushed with N2 three times and protected with N2, and the reaction was heated to reflux for 24 h. After cooling, the reaction was filtered through diatomaceous earth. The yellow solid on the diatomaceous earth was washed twice with methanol and n-hexane, respectively, and dissolved in dichloromethane. The organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to give the yellow solid IrL. a2 (L b1 ) 2 (Metal Complex 2) (1.3 g, yield 24.5%) was obtained. The structure of the product was confirmed to be the target product with a molecular weight of 770.

[0101] Synthesis Example 4: Compound IrL a3 (L b1 Synthesis of 2 (metal complex 3)

[0102] Step 1: [ka] To a dry 500 mL round-bottom flask were added, in order, 6-chloro-dibenzofuran-2-nitrile (5 g, 22.0 mmol), bis(pinacolato)diboron (6.4 g, 25.3 mmol), X-Phos (0.6 g, 1.3 mmol), palladium acetate (0.15 g, 0.6 mmol), potassium acetate (3.2 g, 32.6 mmol), and dioxane (90 mL). The mixture was purged with N three times and heated to reflux under N protection and stirred overnight. After completion of the reaction, the mixture was filtered through diatomaceous earth and anhydrous magnesium sulfate, washed twice with ethyl acetate, and the organic phase was collected and concentrated under reduced pressure to give intermediate 13, which was used directly in the next step.

[0103] Step 2: [ka] To a dry 500 mL round-bottom flask, intermediate 13 (crude), 2-bromopyridine (3.5 g, 22.2 mmol), Pd(dppf)Cl2 (0.48 g, 0.66 mmol), potassium carbonate (3.5 g, 25.3 mmol), 1,4-dioxane (90 mL), and water (30 mL) were added in that order. Under N2 protection, the reaction was heated to reflux for 12 h. After completion of the reaction, the mixture was extracted with ethyl acetate, washed three times with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The crude product was purified by column chromatography to give 3.9 g of intermediate 14 (65.6% yield) as a white solid. The structure of the product was confirmed by NMR and GCMS.

[0104] Step 3: [ka] To a dry 250 mL round-bottom flask, 50 mL each of Intermediate 14 (3.5 g, 12.9 mmol), iridium complex (4.6 g, 6.3 mmol), 2-ethoxyethanol, and DMF were added in order. The reaction was heated at 85 °C for 96 h under N2 protection. After cooling, the reaction mixture was filtered through diatomaceous earth. The mixture was washed twice with methanol and n-hexane, and the yellow solid on the diatomaceous earth was dissolved in dichloromethane. The organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to obtain the yellow solid compound IrL. a3 (L b1 ) 2 (metal complex 3) (2.1 g, 43.3% yield) was obtained. The product was confirmed to be the target product with a molecular weight of 770.

[0105] Synthesis Example 5: Compound IrL a1 (L b3 Synthesis of )2 (metal complex 67)

[0106] Step 1: [ka] To a dry 500 mL round-bottom flask, intermediate 5 (2.4 g, 8.9 mmol), iridium complex (3.3 g, 4.4 mmol), and ethanol (250 mL) were added in that order. The atmosphere was purged with N2 three times and protected with N2, and the reaction was heated to reflux for 24 h. After cooling, the reaction was filtered through diatomaceous earth. The yellow solid on the diatomaceous earth was washed twice with methanol and n-hexane, respectively, and dissolved in dichloromethane. The organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to obtain the yellow solid compound IrL. a1 (L b3 ) 2 (metal complex 67) (2.2 g, 63.7% yield) was obtained. The product was confirmed as the target product with a molecular weight of 798.

[0107] Synthesis Example 6: Compound IrL a1 (L b4 Synthesis of )2 (metal complex 107)

[0108] Step 1: [ka] To a dry 500 mL round-bottom flask, intermediate 5 (2.2 g, 8.1 mmol), iridium complex (4.0 g, 5.4 mmol), and ethanol (120 mL) were added in that order. The atmosphere was purged with N2 three times and protected with N2, and the reaction was heated to reflux for 24 h. After cooling, the reaction was filtered through diatomaceous earth. The mixture was washed twice with methanol and n-hexane, and the yellow solid on the diatomaceous earth was dissolved in dichloromethane. The organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to obtain the yellow solid compound IrL. a1 (L b4 ) 2 (metal complex 107) (0.8 g, 18.6% yield) was obtained. The product was confirmed as the target product with a molecular weight of 798.

[0109] Synthesis Example 7: Compound IrL a1 (L b8 Synthesis of )2 (metal complex 147)

[0110] Step 1: [ka] To a dry 500 mL round-bottom flask, intermediate 5 (2.4 g, 8.9 mmol), iridium complex (3.3 g, 4.4 mmol), and ethanol (250 mL) were added in that order. The atmosphere was purged with N2 three times and protected with N2, and the reaction was heated to reflux for 24 h. After cooling, the reaction was filtered through diatomaceous earth. The yellow solid on the diatomaceous earth was washed twice with methanol and n-hexane, respectively, and dissolved in dichloromethane. The organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to obtain the yellow solid compound IrL. a1 (L b8 ) 2 (metal complex 147) (1.0 g, 27.5% yield) was obtained. The product was confirmed to be the target product with a molecular weight of 826.

[0111] Synthesis Example 8: Compound IrL a221 (L b1 Synthesis of )2 (metal complex 17)

[0112] Step 1: [ka] To a dry 500 mL round-bottom flask, intermediate 4 (7.0 g, 22.0 mmol), 4-methyl-2-bromopyridine (4.2 g, 24.4 mmol), Pd(dppf)Cl (0.67 g, 0.9 mmol), potassium carbonate (6.4 g, 46.3 mmol), dioxane (90 mL), and water (30 mL) were added in that order. Under N protection, the reaction was heated to reflux for 12 h. After completion of the reaction, the mixture was extracted with ethyl acetate, washed three times with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The crude product was purified by column chromatography to give 3 g of intermediate 15 (48.0% yield) as a white solid. The structure of the product was confirmed by NMR and LCMS.

[0113] Step 2: [ka] To a dry 250 mL round-bottom flask, intermediate 15 (3 g, 10.5 mmol), iridium complex (3.5 g, 5 mmol), and 100 mL of ethanol were added in that order. Under N2 protection, the reaction was heated to reflux for 36 h. After cooling, the reaction was filtered through diatomaceous earth. It was washed twice with methanol and n-hexane, and the yellow solid on the diatomaceous earth was dissolved in dichloromethane. The organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to obtain the yellow solid compound IrL. a221 (L b1 ) 2 (metal complex 17) (1.4 g, 33.6% yield) was obtained. The product was confirmed to be the target product with a molecular weight of 784.

[0114] Synthesis Example 9: Compound IrL a962 (L b1 Synthesis of )2 (metal complex 53)

[0115] Step 1: [ka] To a dry 250 mL round-bottom flask, 50 mL each of Intermediate 16 (2.6 g, 9 mmol), iridium complex (3.6 g, 5 mmol), 2-ethoxyethanol, and DMF were added in order. The reaction was heated at 85 °C for 96 h under N2 protection. After cooling, the reaction mixture was filtered through diatomaceous earth. The mixture was washed twice with methanol and n-hexane, and the yellow solid on the diatomaceous earth was dissolved in dichloromethane. The organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to obtain the yellow solid compound IrL. a962 (L b1 ) 2 (metal complex 53) (1.3 g, 33.3% yield) was obtained. The product was confirmed to be the target product with a molecular weight of 787.

[0116] Synthesis Example 10: Compound IrL a962 (L b3 Synthesis of )2 (metal complex 93)

[0117] Step 1: [ka] To a dry 250 mL round-bottom flask, 50 mL each of Intermediate 16 (2.8 g, 9.7 mmol), iridium complex (4.0 g, 5.4 mmol), 2-ethoxyethanol, and DMF were added in order. The reaction was heated at 85 °C for 96 h under N2 protection. After cooling, the reaction mixture was filtered through diatomaceous earth. The mixture was washed twice with methanol and n-hexane, and the yellow solid on the diatomaceous earth was dissolved in dichloromethane. The organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to obtain the yellow solid compound IrL. a962 (L b3 ) 2 (metal complex 93) (0.85 g, 19.3% yield) was obtained. The product was confirmed to be the target product with a molecular weight of 815.

[0118] Synthesis Example 11: Compound IrL a293 (L b1 Synthesis of )2 (metal complex 19)

[0119] Step 1: [ka] To a dry 250 mL round-bottom flask, intermediate 17 (2.6 g, 7.5 mmol), iridium complex (2.2 g, 6.0 mmol), and 150 mL of ethanol were added in that order. Under N2 protection, the reaction was heated to reflux for 24 h. After cooling, the reaction was filtered through diatomaceous earth. The mixture was washed twice with methanol and n-hexane, and the yellow solid on the diatomaceous earth was dissolved in dichloromethane. The organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to obtain the yellow solid compound IrL. a293 (L b1 ) 2 (metal complex 19) (0.6 g, 12% yield) was obtained. The product was confirmed as the target product with a molecular weight of 846.

[0120] Synthesis Example 12: Compound IrL a293 (L b3 Synthesis of )2 (metal complex 77)

[0121] Step 1: [ka] To a dry 250 mL round-bottom flask, intermediate 17 (2.6 g, 7.5 mmol), iridium complex (2.2 g, 6.0 mmol), and 150 mL of ethanol were added in that order. Under N2 protection, the reaction was heated to reflux for 24 h. After cooling, the reaction was filtered through diatomaceous earth. The mixture was washed twice with methanol and n-hexane, and the yellow solid on the diatomaceous earth was dissolved in dichloromethane. The organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to obtain the yellow solid compound IrL. a293 (L b3 ) 2 (metal complex 77) (0.6 g, 12% yield) was obtained. The product was confirmed as the target product with a molecular weight of 874.

[0122] Synthesis Example 13: Compound IrL a987 (L b3 Synthesis of )2 (metal complex 102)

[0123] Step 1: [ka] Intermediate 18 (3.0 g, 8.5 mmol), iridium complex (4.2 g, 5.7 mmol), 2-ethoxyethanol, and DMF (100 mL each) were added to a dry 250 mL round-bottom flask in this order. The reaction was heated at 85 °C for 96 h under N2 protection. After cooling, the reaction mixture was filtered through diatomaceous earth. The mixture was washed twice with methanol and n-hexane, and the yellow solid on the diatomaceous earth was dissolved in dichloromethane. The organic phase was collected, concentrated under reduced pressure, and purified by column chromatography to obtain the yellow solid compound IrL. a987 (L b3) 2 (Metal Complex 102) (0.9 g, 18.0% yield) was obtained. The product was confirmed to be the target product with a molecular weight of 879.

[0124] 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.

[0125] Example of the element

[0126] Example 1

[0127] 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 level of 10 -8 In the case of the ITO anode, the layers were sequentially deposited by hot vacuum evaporation at a rate of 0.2-2 Å / s. Compound HI (100 Å) was used as the hole injection layer (HIL). Compound HT (350 Å) was used as the hole transport layer (HTL). Compound H1 (50 Å) was used as the electron blocking layer (EBL). Then, the compound IrL a1 (L b1 Metal complex 1 (metal complex 1) was doped into host compounds H1 and H2 to form the emissive layer (EML, 8:46:46, 400 Å). Compound H2 (100 Å) was used as the hole-blocking layer (HBL). In the HBL, a mixture of compound ET and 8-hydroxyquinoline-lithium (Liq) was evaporated as the electron-transporting layer (ETL, 40:60, 350 Å). Finally, a 10 Å thick Liq was evaporated as the electron-injecting layer, and a 1200 Å thick Al was evaporated as the cathode. The device was then transferred to a glovebox and encapsulated with a glass cover and a moisture absorbent to complete the device.

[0128] Example 2

[0129] Example 2 shows the use of the compound IrL of the present invention in the light-emitting layer. a2 (L b1 ) 2 (metal complex 2) and the compound IrL a1 (L b1 ) 2 (Metal Complex 1) is replaced, but this is the same as the embodiment in Example 1.

[0130] Example 3

[0131] In Example 3, the compound IrL of the present invention was used in the light-emitting layer. a1 (L b3 ) 2 (metal complex 67) and the compound IrL a1 (L b1 ) 2 (Metal Complex 1) is replaced, but this is the same as the embodiment in Example 1.

[0132] Example 4

[0133] In Example 4, the compound IrL of the present invention was used in the light-emitting layer. a1 (L b4 ) 2 (metal complex 107) and the compound IrL a1 (L b1 ) 2 (Metal Complex 1) is replaced, but this is the same as the embodiment in Example 1.

[0134] Example 5

[0135] In Example 5, the compound IrL of the present invention was used in the light-emitting layer. a1 (L b8 ) 2 (metal complex 147) was used as the compound IrL a1 (L b1 ) 2 (Metal Complex 1) is replaced, but this is the same as the embodiment in Example 1.

[0136] Example 6

[0137] In Example 6, the compound IrL of the present invention was used in the light-emitting layer. a962 (L b1) 2 (metal complex 53) and the compound IrL a1 (L b1 ) 2 (Metal Complex 1) is replaced, but this is the same as the embodiment in Example 1.

[0138] Example 7

[0139] In Example 7, the compound IrL of the present invention was used in the light-emitting layer. a962 (L b3 ) 2 (metal complex 93) and the compound IrL a1 (L b1 ) 2 (Metal Complex 1) is replaced, but this is the same as the embodiment in Example 1.

[0140] Example 8

[0141] In Example 8, the compound IrL of the present invention was used in the light-emitting layer. a293 (L b3 ) 2 (metal complex 77) and the compound IrL a1 (L b1 ) 2 (Metal Complex 1) is replaced, but this is the same as the embodiment in Example 1.

[0142] Example 9:

[0143] In Example 9, the compound IrL of the present invention was used in the light-emitting layer. a987 (L b3 ) 2 (metal complex 102) and the compound IrL a1 (L b1 ) 2 (Metal Complex 1) is replaced, but this is the same as the embodiment in Example 1.

[0144] Comparative Example 1

[0145] In Comparative Example 1, the light-emitting layer contained Comparative Compound 1 and Compound IrL a1 (L b1 ) 2 (Metal Complex 1) is replaced, but this is the same as the embodiment in Example 1.

[0146] The layers of one or more materials used are obtained by doping with different compounds in the weight ratios mentioned above.

[0147] The detailed layer structure and thickness of some of the elements are shown in Table 1. Device structure in device embodiment [Table 8] [Table 9]

[0148] The structure of the material used in the element is represented as follows: [ka] [ka] [ka]

[0149] The device IVL and lifetime characteristics were measured at different current densities and voltages. Table 2 shows the measured external quantum efficiency (EQE), λ, at 1000 nits. max , full width at half maximum (FWHM), voltage (V) and CIE data are shown. Element Data [Table 10]

[0150] Table 3 shows the external quantum efficiency (EQE), λ, measured at 1000 nits for Examples 3 to 9 and Comparative Example 1. max, full width at half maximum (FWHM), voltage (V) and CIE data are shown. The service life (LT97) data for Examples 3 to 9 and Comparative Example 1 are shown for a current of 80 mA / cm 2 The measurement was performed at a constant current of . Element Data [Table 11]

[0151] summary As can be seen from Table 2, the examples of devices containing the compounds of the present invention exhibit several advantages over the comparative compounds. Compared to Comparative Compound 1, the compounds of the present invention unexpectedly exhibit many properties. For example, in Examples 1 and 2, the EQEs reach high efficiencies of 23.62% and 24.81%, respectively, and the voltage is more than 0.2 V lower than in Comparative Example 1, which uses Comparative Compound 1 without cyano group substitution, without any obvious blue-shifted or red-shifted emission. Most surprisingly, the emission peak width is very narrow, particularly in Example 2, where the full width at half maximum is only 42.5 nm, which is unprecedented for a green phosphorescent device. These advantages significantly contribute to improving the level and complexion saturation of green light-emitting devices.

[0152] As can be seen from Table 3, the examples of devices containing the compounds of the present invention exhibit several advantages over the comparative compounds. Examples 3 to 7 exhibit higher EQE (23.25% to 24.15% vs. 22.52%) compared to Comparative Example 1, and their service lives are clearly superior to those of Comparative Example 1 (17.9 h to 23.7 h vs. 15 h). Example 6 has a service life approximately 60% longer than Comparative Example 1 (23.7 h vs. 15 h), and its voltage is 0.2 V to 0.3 V lower than that of Comparative Example 1, which does not have a cyano group substitution.

[0153] Examples 8 and 9 exhibited higher EQE (26.23%, 25.93% vs. 22.52%) and a voltage drop of more than 0.3 V (2.64 V to 2.67 V vs. 2.98 V) compared to Comparative Example 1. Example 9 also exhibited a 14.67% improvement in service life (17.2 h vs. 15 h) compared to Comparative Example 1. Most surprisingly, the emission peak width was very narrow, with the full width at half maximum of Example 8 being only 37.8 nm, which is unprecedented for a green phosphorescent device.

[0154] Example 8 and Example 9 are examples where the substitution positions are hydride and deuteride. Through comparison, the service life of Example 9 is better than that of Example 8, proving the advantage of deuteride in the present invention.

[0155] 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 represented by formula 1 ａ A display comprising a metal complex comprising: 【Chemical 1】 Formula 1 (Cy is 【Chemistry 2】 any structure selected from the group consisting of: "#" represents the position of binding to the metal M, and "*" represents X １ , X ２ , X ３ or X ４ represents the position of attachment to R may represent a single substitution, multiple substitutions up to the highest number of available substitutions, or no substitution, and when multiple R are present in any structure, said R may be the same or different; X １ ~X ４ are each independently C, CR ｘ１ or N, and X １ ~X ４ At least one of X is C and binds to Cy; １ ~X ４ Multiple CRs inside ｘ１ When R ｘ１ may be the same or different, X ５ ~X ８ are each independently CR ｘ２ or N, and X ５ ~X ８ Multiple CRs ｘ２ When R ｘ２ may be the same or different, X is O, S, Se, NR ｘ３ , C.R. ｘ４ R ｘ５ and SiR ｘ６ R ｘ７ selected from the group consisting of R, R ｘ１ , R ｘ２ , R ｘ３ , R ｘ４ , R ｘ５ , R ｘ６ and R ｘ７ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted 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, a carboxyl group, a cyano group, an isocyano group, a thioalkyl group, a phosphino group, and combinations thereof; The R ｘ１ and R ｘ２ at least one of is a cyano group; two adjacent substituents may be bonded to form a ring; X １ , X ２ , X ３ or X ４ is bonded to the metal by a metal-carbon bond or a metal-nitrogen bond.

2. The metal complex has the general formula M(L ａ ) ｍ (L ｂ ) ｎ (L ｃ ) ｑ and the L ａ is a first ligand that forms a coordinate bond with the metal M, and the L ｂ and the L ｃ are a second ligand and a third ligand that form a coordinate bond with the metal M, respectively, and the L ｂ and the L ｃ may be the same or different, Said L ａ , L ｂ and L ｃ may be linked to form a multidentate ligand; m is 1, 2 or 3, n is 0, 1 or 2, q is 0, 1 or 2, and m+n+q equals the oxidation state of M; the metal M is selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir, and Pt; L ａ is, independently, 【Chemistry 3】 【Chemistry 4】 【Chemistry 5】 【Chemistry 6】 selected from the group consisting of X is O, S, Se, NR ｘ３ , C.R. ｘ４ R ｘ５ and SiR ｘ６ R ｘ７ selected from the group consisting of R １ , R ２ , R ３ and R ４ may represent mono-, di-, tri-, tetra- or unsubstituted; R １ , R ２ , R ３ , R ４ , R ｘ３ , R ｘ４ , R ｘ５ , R ｘ６ and R ｘ７ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted 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, a carboxyl group, a cyano group, an isocyano group, a thioalkyl group, a phosphino group, and combinations thereof; R ３ and R ４ at least one of is a cyano group; two adjacent substituents may be bonded to form a ring; L ｂ and L ｃ are each independently 【Chemistry 7】 selected from the group consisting of R ａ , R ｂ , and R ｃ may represent mono-, di-, tri-, tetra- or unsubstituted; X ｂ is O, S, Se, NR Ｎ１ , and C.R. Ｃ１ R Ｃ２ selected from the group consisting of R ａ , R ｂ , R ｃ , R Ｎ１ , R Ｃ１ and R Ｃ２ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted 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, a carboxyl group, a cyano group, an isocyano group, a thioalkyl group, a phosphino group, and combinations thereof; The display of claim 1 , wherein two adjacent substituents may be bonded to form a ring.

3. 3. The display of claim 2, wherein the metal M is selected from Pt, Os, or Ir.

4. The display of claim 2, wherein the metal complex has a structure represented by any one of formulas 2 to 10. 【Chemistry 8】 【Chemistry 9】 m is 1, 2 or 3; X is selected from O, S or Se; R １ , R ３ and R ４ may represent mono-, di-, tri-, tetra- or unsubstituted; R ａ , R ｂ , and R ｃ may represent mono-, di-, tri-, tetra- or unsubstituted; R １ , R ３ , R ４ , R ａ , R ｂ and R ｃ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted 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, a carboxyl group, a cyano group, an isocyano group, a thioalkyl group, a phosphino group, and combinations thereof; R ３ and R ４ at least one of is a cyano group; Two adjacent substituents may be bonded to form a ring.

5. The display of claim 4, wherein the metal complex has a structure represented by formula 2-a. 【Chemistry 10】 m is 1, 2 or 3; X is selected from O, S or Se; R ３ and R ４ may represent mono-, di-, tri-, tetra- or unsubstituted; R ａ , R ｂ , and R ｃ may represent mono-, di-, tri-, tetra- or unsubstituted; R １１ , R １２ , R １３ , R １４ , R ３ , R ４ , R ａ , and R ｂ are each independently 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 selected from the group consisting of unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amine groups, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, thioalkyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof, R ３ , R ４ at least one of is a cyano group; Two adjacent substituents may be bonded to form a ring.

6. R １１ and R １４ are both hydrogen, R １２ and R １３ are each independently 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 heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted amine group having 0 to 20 carbon atoms, a carboxyl group, a cyano group, an isocyano group, a thioalkyl group, a phosphino group, and combinations thereof; and R １２ and R １３ the sum of the numbers of carbon atoms in Or, R １１ and R １４ If at least one of is not hydrogen, then R １２ and R １３ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted 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, a carboxyl group, a cyano group, an isocyano group, a thioalkyl group, a phosphino group, and combinations thereof.

7. R １１ , R １２ , R １３ , R １４ , R ａ , and R ｂ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and combinations thereof; R ３ and R ４ are each independently 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 cyano group, and combinations thereof; R ３ , R ４ The display of claim 5 , wherein at least one of is a cyano group.

8. In the formula 1, X ５ ~X ８ At least one of the following is CR ｘ２ and the R ｘ２ The display of claim 1 , wherein is a cyano group.

9. In the formula 1, X ５ ~X ８ are each independently CR ｘ２ and wherein R ｘ２ The display of claim 1 , wherein at least one of is a cyano group.

10. In the formula 1, X ７ is CR ｘ２ and wherein R ｘ２ at least one of X is a cyano group, or ８ is CR ｘ２ and wherein R ｘ２ The display of claim 1 , wherein at least one of is a cyano group.

11. R ４ may represent mono-, di-, tri- or tetra-substitution, R ４ When there are a plurality of R ４ is selected from the group consisting of deuterium, 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 cyano group, and combinations thereof; R ４ The display of claim 4 or 5, wherein at least one of the groups is a cyano group.

12. R ４ may represent mono-, di-, tri- or tetra-substitution, R ４ When there are a plurality of R ４ is selected from the group consisting of deuterium, 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 cyano group, and combinations thereof; R ４ at least one of is a cyano group; R ３ may represent mono-, di-, or unsubstituted; R ３ When there are a plurality of R ３ is selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, and combinations thereof.

13. Ligand L ａ teeth, 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 【Chemistry 18】 【Chemistry 19】 【Chemistry 20】 【Chemical 21】 【Chemical 22】 【Chemical 23】 【Chemistry 24】 【Chemistry 25】 【Chemical 26】 【Chemical 27】 ​ 【Chemical 29】 【Chemistry 30】 【Chemical 31】 【Chemical 32】 【Chemical 33】 【Chemical 34】 【Chemical 35】 【Chemical 36】 【Chemical 37】 【Chemical 38】 【Chemical 39】 【Chemistry 40】 【Chemistry 41】 【Chemistry 42】 【Chemistry 43】 【Chemical 44】 【Chemistry 45】 【Chemistry 46】 【Chemistry 47】 【Chemistry 48】 【Chemistry 49】 【Chemistry 50】 【Chemistry 51】 【Chemistry 52】 【Chemistry 53】 【Chemical 54】 【Chemistry 55】 【Chemical 56】 【Chemical 57】 【Chemistry 58】 【Chemical 59】 【Chemistry 60】 【Hua 61】 3. The display of claim 2, wherein the display is selected from the group consisting of:

14. Said L ａ The display of claim 13 , wherein:

15. Said L ａ The hydrogen atoms in the aryl group may be partially or completely deuterated, Or the L ａ The display of claim 13 , wherein the hydrogen atoms in the alkyl groups of the formula (I) may be partially or completely deuterated.

16. The metal complex has the formula IrL ａ (L ｂ ) ２ or Ir(L ａ ) ２ L ｂ and L ａ Is, L ａ１ ~L ａ３９２ and L ａ４０８ ~L ａ１０１９ One or two selected from L ｂ teeth, 【Hua 62】 【Chemistry 63】 【Hua 64】 The display according to claim 13, wherein the display comprises one or two selected from the group consisting of:

17. The metal complex has the formula Ir(L ａ ) ２ L ｃ or IrL ａ (L ｃ ) ２ and L ａ Is, L ａ１ ~L ａ３９２ and L ａ４０８ ~L ａ１０１９ One or two selected from L ｃ teeth, 【Chemistry 65】 【Hua 66】 【Chemical 67】 【Chemistry 68】 [Chemical Formula 69] 【Chemistry 70】 【Chemical 71】 【Chemical 72】 【Chemical 73】 【Chemical 74】 【Chemistry 75】 【Chemical 76】 【Chemical 77】 【Chemical 78】 The display according to claim 16, wherein the compound is one or two selected from the group consisting of:

18. The metal complex is selected from the structures represented by any one of Metal Complex 1 to Metal Complex 316, Metal complexes 1 to 226 are IrL ａ (L ｂ ) ２ and two L ｂ are identical, and L ａ and L ｂ correspond to the structures shown in the table below, 【Table 1】 【Table 2】 【Table 3】 【Table 4】 【Table 5】 Metal complexes 227 to 274 are Ir(L ａ ) ２ L ｃ and two L ａ are identical, and L ａ and L ｃ correspond to the structures shown in the table below, 【Table 6】 【Table 7】 Metal complexes 275 to 316 are Ir(L ａ ) ３ and has the structure of three L ａ are identical, and L ａ 18. The display of claim 17, wherein: 【Table 8】

19. Ligand L represented by formula 1 ａ A lighting panel comprising a metal complex comprising: 【Chemical 79】 Formula 1 (Cy is 【Chemistry 80】 any structure selected from the group consisting of: "#" represents the position of binding to the metal M, and "*" represents X １ , X ２ , X ３ or X ４ represents the position of attachment to R may represent a single substitution, multiple substitutions up to the highest number of available substitutions, or no substitution, and when multiple R are present in any structure, said R may be the same or different; X １ ~X ４ are each independently C, CR ｘ１ or N, and X １ ~X ４ At least one of X is C and binds to Cy; １ ~X ４ Multiple CRs inside ｘ１ When R ｘ１ may be the same or different, X ５ ~X ８ are each independently CR ｘ２ or N, and X ５ ~X ８ Multiple CRs ｘ２ When R ｘ２ may be the same or different, X is O, S, Se, NR ｘ３ , C.R. ｘ４ R ｘ５ and SiR ｘ６ R ｘ７ selected from the group consisting of R, R ｘ１ , R ｘ２ , R ｘ３ , R ｘ４ , R ｘ５ , R ｘ６ and R ｘ７ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted 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, a carboxyl group, a cyano group, an isocyano group, a thioalkyl group, a phosphino group, and combinations thereof; The R ｘ１ and R ｘ２ at least one of is a cyano group; two adjacent substituents may be bonded to form a ring; X １ , X ２ , X ３ or X ４ is bonded to the metal by a metal-carbon bond or a metal-nitrogen bond.

20. Ligand L represented by formula 1 ａ 10. Use of a metal complex comprising: 【Chemistry 81】 Formula 1 (Cy is 【Chemistry 82】 【Chemistry 83】 any structure selected from the group consisting of: "#" represents the position of binding to the metal M, and "*" represents X １ , X ２ , X ３ or X ４ represents the position of attachment to R may represent a single substitution, multiple substitutions up to the highest number of available substitutions, or no substitution, and when multiple R are present in any structure, said R may be the same or different; X １ ~X ４ are each independently C, CR ｘ１ or N, and X １ ~X ４ At least one of X is C and binds to Cy; １ ~X ４ Multiple CRs inside ｘ１ When R ｘ１ may be the same or different, X ５ ~X ８ are each independently CR ｘ２ or N, and X ５ ~X ８ Multiple CRs ｘ２ When R ｘ２ may be the same or different, X is O, S, Se, NR ｘ３ , C.R. ｘ４ R ｘ５ and SiR ｘ６ R ｘ７ selected from the group consisting of R, R ｘ１ , R ｘ２ , R ｘ３ , R ｘ４ , R ｘ５ , R ｘ６ and R ｘ７ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted 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, a carboxyl group, a cyano group, an isocyano group, a thioalkyl group, a phosphino group, and combinations thereof; The R ｘ１ and R ｘ２ at least one of is a cyano group; two adjacent substituents may be bonded to form a ring; X １ , X ２ , X ３ or X ４ is bonded to the metal by a metal-carbon bond or a metal-nitrogen bond.

21. Ligand L represented by formula 1 ａ 10. Use of a metal complex comprising: 【Chemistry 84】 Formula 1 (Cy is 【Chemistry 85】 any structure selected from the group consisting of: "#" represents the position of binding to the metal M, and "*" represents X １ , X ２ , X ３ or X ４ represents the position of attachment to R may represent a single substitution, multiple substitutions up to the highest number of available substitutions, or no substitution, and when multiple R are present in any structure, said R may be the same or different; X １ ~X ４ are each independently C, CR ｘ１ or N, and X １ ~X ４ At least one of X is C and binds to Cy; １ ~X ４ Multiple CRs inside ｘ１ When R ｘ１ may be the same or different, X ５ ~X ８ are each independently CR ｘ２ or N, and X ５ ~X ８ Multiple CRs ｘ２ When R ｘ２ may be the same or different, X is O, S, Se, NR ｘ３ , C.R. ｘ４ R ｘ５ and SiR ｘ６ R ｘ７ selected from the group consisting of R, R ｘ１ , R ｘ２ , R ｘ３ , R ｘ４ , R ｘ５ , R ｘ６ and R ｘ７ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted 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, a carboxyl group, a cyano group, an isocyano group, a thioalkyl group, a phosphino group, and combinations thereof; The R ｘ１ and R ｘ２ at least one of is a cyano group; two adjacent substituents may be bonded to form a ring; X １ , X ２ , X ３ or X ４ is bonded to the metal by a metal-carbon bond or a metal-nitrogen bond.

22. A wearable device comprising the display of claim 1 or the lighting panel of claim 19.

23. A wearable device comprising the display of claim 1 or the lighting panel of claim 19.

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