JP7530645B2 - Organic Light Emitting Materials - Google Patents

Description

The present invention relates to compounds for use in organic electronic devices, such as organic light-emitting devices. More particularly, the present invention relates to metal complexes containing ligands having a structure represented by formula 1 or formula 1', electroluminescent devices containing the metal complexes, and compound formulations.

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.

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

OLEDs are divided into three different types according to their emission mechanism. The OLED invented by Tang and van Slyke is a fluorescent OLED, which uses only singlet emission. This limitation impedes the commercialization of OLEDs, since the triplets generated in the device are wasted by non-radiative decay pathways, and the internal quantum efficiency (IQE) of fluorescent OLEDs is only 25%. In 1997, Forrest and Thompson reported a phosphorescent OLED that uses triplet emission from heavy metal containing complexes as an emitter. Therefore, singlets and triplets can be harvested and 100% IQE can be achieved. Due to its high efficiency, the discovery and development of phosphorescent OLEDs directly contributes to the commercialization of active matrix OLEDs (AMOLEDs). Recently, Adachi has achieved high efficiency through thermally activated delayed fluorescence (TADF) of organic compounds. These emitters have a small singlet-triplet gap, allowing the exciton to transition from triplet back to singlet. In TADF devices, the high IQE is due to triplet excitons threading between reverse systems (reverse intersystem crossing) to generate singlet excitons.

OLEDs may be further divided into small molecule and polymer OLEDs depending on the form of the material required. Small molecules refer to materials that are not polymeric, either organic or organometallic, and the molecular weight of small molecules may be large as long as they have a precise structure. 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. Small molecule OLEDs can become polymer OLEDs when post-polymerization occurs during the manufacturing process.

Various methods for manufacturing OLEDs are known. Small molecule OLEDs are typically manufactured by vacuum thermal evaporation. Polymer OLEDs are manufactured by solution processes, e.g. spin coating, inkjet printing and nozzle printing. Small molecule OLEDs can also be manufactured by solution processes, provided the materials can be dissolved or dispersed in a solvent.

The emission color of an OLED can be achieved by the structural design of the emitting material. An OLED may include one or more emitting layers to achieve a desired spectrum. In green, yellow, and red OLEDs, phosphorescent materials have already been successfully commercialized, but blue phosphorescent elements still have problems such as blue not being saturated, short lifetime, and high operating voltage. Commercial full-color OLED displays generally use a mixed strategy, using blue fluorescence and yellow, red, or green phosphorescence. Currently, there is a problem that the efficiency of phosphorescent OLEDs drops rapidly at high brightness. It is also desirable to have a more saturated emission spectrum, higher efficiency, and longer device lifetime.

Phosphorescent metal complexes are applied in the field of organic electroluminescence lighting or display as phosphorescent doping materials in the light-emitting layer. In order to meet the needs of different cases, by adjusting different substituents in the ligands of the materials, adjustments to the complexion of the materials can be realized on a certain basis, and phosphorescent metal complexes with different emission wavelengths can be obtained.

CN104335377A (Patent Document 1) discloses a compound having the following structure:

そのうち、一連の

および類似する構造を有する。該発明出願者は、該構造の材料が高いＥＬ効率および良好な耐用年数を有することを指摘してしまうが、ジアゾール／トリアゾールを含有する二窒素配位子の金属錯体における適用に対する研究に専念しながら、特定の環に置換されたＲ^１基がシリル基である場合の利点に着目していない。

Among them, a series of

The applicant points out that the material of this structure has high EL efficiency and good service life, but while concentrating on the research on the application of dinitrogen ligands containing diazole/triazole in metal complexes, he does not pay attention to the advantage of the case where the R ¹ group substituted on a specific ring is a silyl group.

CN107973823A (Patent Document 2) discloses compounds with quinolinyldibenzo-substituted ligands.

ただし、Ｒ_１～Ｒ_４は、水素、アルキル基、ヘテロアルキル基、アリール基またはヘテロアリール基から選ばれてもよい。該発明出願者は、該構造の材料が良好な安定性、耐用年数および顔色飽和度を有することを指摘してしまうが、開示された構造における置換基Ｒ_１～Ｒ_４はそれぞれ水素またはアルキル基であり、特定の環にシリル置換基を有する場合の利点が開示または示唆されていない。

However, R ₁ to R ₄ may be selected from hydrogen, alkyl groups, heteroalkyl groups, aryl groups, or heteroaryl groups. The applicant points out that the material of the structure has good stability, service life, and color saturation, but the substituents R ₁ to R ₄ in the disclosed structure are each hydrogen or alkyl groups, and the advantage of having a silyl substituent on a specific ring is not disclosed or suggested.

Although metal complexes with quinoline ligands already exist, their related performance, such as luminous color, device efficiency, device service life, etc., is still lacking, and the research on related materials still needs to be delved deeper.

China Patent Application Publication No. 104335377 China Patent Application Publication No. 107973823

Applied Physics Letters, 1987, 51(12):913-915

In order to solve at least part of the above-mentioned problems, the present invention aims to provide a metal complex containing a ligand having a structure represented by formula 1 or formula 1'. The metal complex can be used as a light-emitting material in an organic electroluminescent device. These novel metal complexes can effectively adjust the emission complexion to deep red, improve the external quantum efficiency of the device while maintaining a narrow full width at half maximum, and provide better device performance.

According to one embodiment of the present invention, there is disclosed a metal complex having a maximum emission wavelength of 612 nm or more, preferably 615 nm or more in a photoluminescence spectrum (PL), wherein the metal in the metal complex is selected from metals having a relative atomic mass of more than 40, and the metal complex comprises a ligand _La having a structure represented by formula 1.

（Ｚは、Ｏから選ばれ、
Ｘ_１～Ｘ_８は、出現毎に同一または異なってＣ、ＣＲ_ｘまたはＮから選ばれ、
Ｙ_１～Ｙ_６は、出現毎に同一または異なってＣＲ_ｙまたはＮから選ばれ、
Ｒ_ｘ、Ｒ_ｙは、出現毎に同一または異なって水素、重水素、ハロゲン、置換または非置換の炭素原子数１～２０のアルキル基、置換または非置換の環炭素原子数３～２０のシクロアルキル基、置換または非置換の炭素原子数１～２０のヘテロアルキル基、置換または非置換の炭素原子数７～３０のアラルキル基、置換または非置換の炭素原子数１～２０のアルコキシ基、置換または非置換の炭素原子数６～３０のアリールオキシ基、置換または非置換の炭素原子数２～２０のアルケニル基、置換または非置換の炭素原子数６～３０のアリール基、置換または非置換の炭素原子数３～３０のヘテロアリール基、置換または非置換の炭素原子数３～２０のアルキルシリル基、置換または非置換の炭素原子数６～２０のアリールシリル基、置換または非置換の炭素原子数０～２０のアミン基、アシル基、カルボニル基、カルボキシル基、エステル基、シアノ基、イソシアノ基、ヒドロキシル基、スルファニル基、スルフィニル基、スルホニル基、ホスフィノ基およびこれらの組合せからなる群から選ばれ、
隣り合う置換基Ｒ_ｘは、結合して環を形成していてもよい。）

Z is selected from O;
X ₁ to X ₈ are each identically or differently selected from C, CR _x or N;
Y ₁ to Y ₆ are each identically or differently selected from CR _y or N at each occurrence;
R _x and R _y each occur the same or different and each represent 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 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, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxyl group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof, each of which has 0 to 20 carbon atoms;
Adjacent substituents R _x may be bonded to form a ring.

According to one embodiment of the present invention, there is disclosed a metal complex, wherein the metal in the metal complex is selected from metals having a relative atomic mass greater than 40, and the metal complex comprises a ligand L _a having a structure represented by Formula 1′.

（Ｚは、Ｏ、ＳまたはＳｅから選ばれ、
Ｘ_１～Ｘ_８は、出現毎に同一または異なってＣ、ＣＲ_ｘまたはＮから選ばれ、
Ｙ_１～Ｙ_６は、出現毎に同一または異なってＣＲ_ｙ１、ＣＲ_ｙ２またはＮから選ばれ、且つＹ_１～Ｙ_６のうちの少なくとも１つは、ＣＲ_ｙ２から選ばれ、前記Ｒ_ｙ２は、－Ｌ－ＳｉＲ_ｓ１Ｒ_ｓ２Ｒ_ｓ３の構造を有し、
Ｒ_ｘ、Ｒ_ｙ１、Ｒ_ｓ１、Ｒ_ｓ２、Ｒ_ｓ３は、出現毎に同一または異なって水素、重水素、ハロゲン、置換または非置換の炭素原子数１～２０のアルキル基、置換または非置換の環炭素原子数３～２０のシクロアルキル基、置換または非置換の炭素原子数１～２０のヘテロアルキル基、置換または非置換の炭素原子数７～３０のアラルキル基、置換または非置換の炭素原子数１～２０のアルコキシ基、置換または非置換の炭素原子数６～３０のアリールオキシ基、置換または非置換の炭素原子数２～２０のアルケニル基、置換または非置換の炭素原子数６～３０のアリール基、置換または非置換の炭素原子数３～３０のヘテロアリール基、置換または非置換の炭素原子数３～２０のアルキルシリル基、置換または非置換の炭素原子数６～２０のアリールシリル基、置換または非置換の炭素原子数０～２０のアミン基、アシル基、カルボニル基、カルボキシル基、エステル基、シアノ基、イソシアノ基、ヒドロキシル基、スルファニル基、スルフィニル基、スルホニル基、ホスフィノ基およびこれらの組合せからなる群から選ばれ、
Ｌは、単結合、置換または非置換の炭素原子数１～２０のアルキレン基、置換または非置換の炭素原子数３～２０のシクロアルキレン基、置換または非置換の炭素原子数６～２０のアリーレン基、置換または非置換の炭素原子数３～２０のヘテロアリーレン基、またはこれらの組合せからなる群から選ばれ、
隣り合う置換基Ｒ_ｘ、Ｒ_ｓ１、Ｒ_ｓ２、Ｒ_ｓ３は、結合して環を形成していてもよい。）

Z is selected from O, S or Se;
X ₁ to X ₈ are each identically or differently selected from C, CR _x or N;
Y ₁ to Y ₆ are each the same or different and selected from CR _y1 , CR _y2 or N, and at least one of Y ₁ to Y ₆ is selected from CR _y2 , said R _y2 having the structure -L-SiR _s1 R _s2 R _s3 ;
R _x , R _y1 , R _s1 , R _s2 and R _s3 each occur the same or different and each represent 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 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, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxyl group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof, each of which has 0 to 20 carbon atoms;
L is selected from the group consisting of a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;
Adjacent substituents R _x , R _s1 , R _s2 and R _s3 may be bonded to form a ring.

According to another embodiment of the present invention, there is further disclosed an electroluminescent device including an anode, a cathode, and an organic layer disposed between the anode and the cathode, the organic layer including a metal complex whose specific structure is shown in any one of the above-mentioned embodiments.

According to another embodiment of the present invention, a formulation of a compound containing a metal complex as described above is further disclosed.

The novel metal complexes containing a ligand having the structure of formula 1 or formula 1' according to the present invention can be used as luminescent materials in electroluminescent devices. These novel metal complexes can effectively adjust the emission complexion to deep red, improve the external quantum efficiency of the device while maintaining a narrow full width at half maximum, and provide better device performance.

FIG. 1 is a schematic diagram of an organic light emitting device that may include metal complex and compound formulations according to the present invention. 1 is a schematic diagram of another organic light emitting device that may include metal complex and compound formulations according to the present invention.

OLEDs can be fabricated on a variety of substrates, such as glass, plastic, and metal. FIG. 1 illustrates an exemplary, non-limiting organic light-emitting device 100. The drawings are not necessarily drawn to scale, and some layer structures may be omitted in the drawings, as necessary. Device 100 may include substrate 101, anode 110, hole injection layer 120, hole transport layer 130, electron blocking layer 140, light-emitting layer 150, hole blocking layer 160, electron transport layer 170, electron injection layer 180, and 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.

There are many examples of each of these layers. Illustratively, a flexible and transparent substrate-anode combination is disclosed in U.S. Pat. No. 5,844,363, which is incorporated herein by reference in its entirety. For example, U.S. Pat. App. Pub. No. 2003/0230980, which is incorporated herein by reference in its entirety, discloses an example of a p-type doped hole transport layer that is m-MTDATA doped with F ₄ -TCNQ at a molar ratio of 50:1. Example host materials are disclosed in U.S. Pat. No. 6,303,238 to Thompson et al., which is incorporated herein by reference in its entirety. For example, U.S. Pat. App. Pub. No. 2003/0230980, which is incorporated herein by reference in its entirety, discloses an example of an n-type doped electron transport layer that is BPhen doped with Li at a molar ratio of 1:1. Examples of cathodes are disclosed in U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, including composite cathodes having a thin metal layer, such as Mg:Ag, and a sputter-deposited transparent conductive ITO layer coated thereon. U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003/0230980, which are incorporated by reference in their entirety, describe the principles and use of blocking layers in more detail. Examples of injection layers are provided in U.S. Patent Application Publication No. 2004/0174116, which is incorporated by reference in its entirety. Protective layers are described in U.S. Patent Application Publication No. 2004/0174116, which is incorporated by reference in its entirety.

The above-mentioned split layer structure is provided by way of non-limiting examples. The functionality of an OLED can be realized 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 of the functional layers may include multiple sub-layers, for example, an emissive layer may have two layers of different emissive materials to achieve a desired emission spectrum.

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.

OLEDs also require an encapsulation layer, and as shown in FIG. 2, an organic light-emitting device 200 is shown by way of example and without limitation. The difference from FIG. 1 is that it may include an encapsulation layer 102 on the cathode 190 to prevent harmful substances from the outside, such as moisture and oxygen. Any material that can provide an encapsulation function, such as glass or an organic-inorganic mixed layer, may be used as the encapsulation layer. The encapsulation layer should be disposed directly or indirectly on the outside of the OLED element. Multilayer thin-film encapsulation is described in US Pat. No. 7,968,146 B2, the entire contents of which are incorporated herein by reference.

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. These consumer products include, for example, flat panel displays, monitors, medical monitors, televisions, billboards, indoor or outdoor lighting and/or signaling lamps, heads-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, in-vehicle displays, and tail lights.

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

"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 disposed relatively far from the substrate. Other layers may be present between the first and second layers, unless the first layer is specified as being "in contact with" the second layer. Illustratively, the cathode may be described as being "on" the anode, even if there are various organic layers between the cathode and anode.

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

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

It is believed that the internal quantum efficiency (IQE) of fluorescent OLEDs may exceed the 25% spin-statistic 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).

On the other hand, E-type delayed fluorescence depends on the conversion of excited states between triplet and singlet, not on the collision of two triplets. Compounds capable of generating E-type delayed fluorescence need to have an extremely small singlet-triplet gap to convert the energy state. Thermal energy can activate the transition from triplet to singlet. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). The notable feature of TADF is that the delayed component increases with increasing temperature. If the rate of threading (reverse intersystem crossing) between reverse systems (RISC) is fast enough, the proportion of backfilled singlet excited states can reach 75%, minimizing non-radiative decay from triplets. The total proportion of singlets can be 100%, far exceeding the 25% of exciton spin statistics due to electro.

The characteristics of E-type delayed fluorescence can be seen from an excited complex system or a single compound. Without being limited to theory, E-type delayed fluorescence requires that the emitting material has a small singlet-triplet energy gap (ΔE _S-T ). Organic non-metal-containing donor-acceptor emitting materials may achieve this. The emission of these materials is usually characterized as donor-acceptor charge transition (CT) type emission. In these donor-acceptor type compounds, the spatial separation between the HOMO and LUMO generally produces a small ΔE _S-T . These states may include CT states. Donor-acceptor emitting materials are usually 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).

Definition of the technical terms for substituents

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

As used herein, alkyl groups include straight-chain and branched-chain alkyl groups. The alkyl group may be an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 12 carbon atoms, and more preferably an alkyl group having 1 to 6 carbon atoms. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, and 3-methylpentyl. The alkyl group may also be substituted. The carbons in the alkyl group chain may be replaced with other heteroatoms. Of these, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl, and n-hexyl are preferred. The alkyl group may also be substituted.

As used herein, cycloalkyl groups include cyclic alkyl groups. The cycloalkyl groups may be cycloalkyl groups having 3 to 20 ring carbon atoms, and preferably cycloalkyl groups having 4 to 10 carbon atoms. Examples of cycloalkyl groups include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, and 2-norbornyl. Of these, cyclobutyl, cyclopentyl, 4-methylcyclohexyl, and 4,4-dimethylcyclohexyl are preferred. The cycloalkyl groups may also be substituted.

Heteroalkyl groups, as used herein, include those in which one or more carbons in the alkyl chain are replaced with a heteroatom selected from the group consisting of nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium, and boron. The heteroalkyl group may be a heteroalkyl group having 1 to 20 carbon atoms, preferably a heteroalkyl group having 1 to 10 carbon atoms, and more preferably a heteroalkyl group having 1 to 6 carbon atoms. Examples of heteroalkyl groups include oxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, sulfanylmethyl, sulfanylethyl, sulfanylpropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, tert-butyltriethylsilyl, triisopropylsilyl, trimethylsilylmethyl, trimethylsilylethyl, and trimethylsilylisopropyl. The heteroalkyl group may also be substituted.

Alkenyl groups, as used herein, include linear, branched, and cyclic olefin groups. A linear alkenyl group may be an alkenyl group having 2 to 20 carbon atoms, and preferably an alkenyl group having 2 to 10 carbon atoms. Examples of alkenyl groups include ethyl, propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cycloheptatrienyl, cyclooctenyl, cyclooctatetraenyl, and norbornenyl. The alkenyl group may also be substituted.

As used herein, alkynyl groups include straight chain alkynyl groups. The alkynyl group may be an alkynyl group having 2 to 20 carbon atoms, and preferably is an alkynyl group having 2 to 10 carbon atoms. Examples of alkynyl groups include ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3,3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3,3-diisopropyl-1-pentynyl, phenylethynyl, phenylpropynyl, and the like. As described above, preferred examples include ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, and phenylethynyl. The alkynyl group may also be substituted.

Aryl or aromatic groups, as used herein, contemplate non-fused and fused systems. The aryl group may be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene, and preferably include phenyl, biphenyl, terphenyl, triphenylene, fluorenyl, and naphthalene. 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. The aryl group may also be substituted.

Heteroaryl groups, as used herein, may include non-fused and fused heteroaromatic groups having 1 to 5 heteroatoms, at least one of which is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron. Isoaryl groups also refer to heteroaryl groups. Heteroaryl groups may be heteroaryl groups having 3 to 30 carbon atoms, preferably heteroaryl groups having 3 to 20 carbon atoms, and more preferably heteroaryl groups having 3 to 12 carbon atoms. Suitable heteroaryl groups are dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridoindole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indenoazine, benzoxazole, benzisoxazole. , 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 its aza analogues. Heteroaryl groups may also be substituted.

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

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

As used herein, an aralkyl group includes an alkyl group substituted with an aryl group. The aralkyl group may be an aralkyl group having 7 to 30 carbon atoms, preferably an aralkyl group having 7 to 20 carbon atoms, and more preferably an aralkyl group having 7 to 13 carbon atoms. Examples of 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, o ... These 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 these, benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, and 2-phenylisopropyl are preferred. The aralkyl group may also be substituted.

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

As used herein, an arylsilyl group includes a silyl group substituted with at least one aryl group. The arylsilyl group may be an arylsilyl group having 6 to 30 carbon atoms, and is preferably an arylsilyl group having 8 to 20 carbon atoms. Examples of arylsilyl groups include triphenylsilyl, phenyldiphenylsilyl, diphenylbiphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, diphenyl-tert-butylsilyl, tri-tert-butylsilyl, dimethyl-tert-butylsilyl, and methyldi-tert-butylsilyl. The arylsilyl group may also be substituted.

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

In the present invention, unless otherwise specified, the use of any of the terms from the group consisting of substituted alkyl group, substituted cycloalkyl group, substituted heteroalkyl group, substituted aralkyl group, substituted alkoxy group, substituted aryloxy group, substituted alkenyl group, substituted alkynyl group, substituted aryl group, substituted heteroaryl group, substituted alkylsilyl group, substituted arylsilyl group, substituted amine group, substituted acyl group, substituted carbonyl group, substituted carboxyl group, substituted ester group, substituted sulfinyl group, substituted sulfonyl group, and substituted phosphino group means that any of the groups from the alkyl group, cycloalkyl group, heteroalkyl group, aralkyl group, alkoxy group, aryloxy group, alkenyl group, alkynyl group, aryl group, heteroaryl group, alkylsilyl group, arylsilyl group, amine group, acyl group, carbonyl group, carboxyl group, ester group, sulfinyl group, sulfonyl group, and phosphino group is a deuterium, halogen, unsubstituted 1 to 20 carbon atom. It means that the alkyl group may be substituted with one or more selected from an alkyl group having 3 to 20 ring carbon atoms, an unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, an unsubstituted heteroalkyl group having 1 to 20 carbon atoms, an unsubstituted aralkyl group having 7 to 30 carbon atoms, an unsubstituted alkoxy group having 1 to 20 carbon atoms, an unsubstituted aryloxy group having 6 to 30 carbon atoms, an unsubstituted alkenyl group having 2 to 20 carbon atoms, an unsubstituted alkynyl group having 2 to 20 carbon atoms, an unsubstituted aryl group having 6 to 30 carbon atoms, an unsubstituted heteroaryl group having 3 to 30 carbon atoms, an unsubstituted alkylsilyl group having 3 to 20 carbon atoms, an unsubstituted arylsilyl group having 6 to 20 carbon atoms, an unsubstituted amine group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

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

In the compounds referred to herein, hydrogen atoms may be partially or completely replaced with deuterium. Other atoms, such as carbon and nitrogen, may also be replaced with their other stable isotopes. Substitution of other stable isotopes in the compounds may be preferred to improve the efficiency and stability of the device.

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.

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

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

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

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

According to one embodiment of the present invention, there is disclosed a metal complex having a maximum emission wavelength of 612 nm or more, preferably 615 nm or more in a photoluminescence spectrum (PL), wherein the metal in the metal complex is selected from metals having a relative atomic mass of more than 40, and the metal complex comprises a ligand _La having a structure represented by formula 1.

（Ｚは、Ｏから選ばれ、
Ｘ_１～Ｘ_８は、出現毎に同一または異なってＣ、ＣＲ_ｘまたはＮから選ばれ、
Ｙ_１～Ｙ_６は、出現毎に同一または異なってＣＲ_ｙまたはＮから選ばれ、
Ｒ_ｘ、Ｒ_ｙは、出現毎に同一または異なって水素、重水素、ハロゲン、置換または非置換の炭素原子数１～２０のアルキル基、置換または非置換の環炭素原子数３～２０のシクロアルキル基、置換または非置換の炭素原子数１～２０のヘテロアルキル基、置換または非置換の炭素原子数７～３０のアラルキル基、置換または非置換の炭素原子数１～２０のアルコキシ基、置換または非置換の炭素原子数６～３０のアリールオキシ基、置換または非置換の炭素原子数２～２０のアルケニル基、置換または非置換の炭素原子数６～３０のアリール基、置換または非置換の炭素原子数３～３０のヘテロアリール基、置換または非置換の炭素原子数３～２０のアルキルシリル基、置換または非置換の炭素原子数６～２０のアリールシリル基、置換または非置換の炭素原子数０～２０のアミン基、アシル基、カルボニル基、カルボキシル基、エステル基、シアノ基、イソシアノ基、ヒドロキシル基、スルファニル基、スルフィニル基、スルホニル基、ホスフィノ基およびこれらの組合せからなる群から選ばれ、
隣り合う置換基Ｒ_ｘは、結合して環を形成していてもよい。）

Z is selected from O;
X ₁ to X ₈ are each identically or differently selected from C, CR _x or N;
Y ₁ to Y ₆ are each identically or differently selected from CR _y or N at each occurrence;
R _x and R _y each occur the same or different and each represent 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 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, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxyl group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof, each of which has 0 to 20 carbon atoms;
Adjacent substituents R _x may be bonded to form a ring.

In this specification, the phrase "adjacent substituents R _x may be bonded to form a ring" means that when there are multiple substituents R _x , any adjacent substituents R _x may be bonded to form a ring. Obviously, when there are multiple substituents R _x , any adjacent substituents R _x may not be bonded to form a ring. Any adjacent substituents R _y cannot be bonded to form a ring.

In this embodiment, the metal complex has a maximum emission wavelength of 612 nm or more in the photoluminescence spectrum (PL) means that when the metal complex is dissolved in anhydrous dichloromethane to prepare a solution with a concentration of 3×10 ⁻⁵ mol/L, and the photoluminescence spectrum (PL) of the metal complex solution is measured at room temperature (298 K) using a fluorescence spectrophotometer, the maximum emission wavelength in the photoluminescence spectrum of the metal complex is 612 nm or more. Preferably, the metal complex has a maximum emission wavelength of 615 nm or more in the photoluminescence spectrum. More preferably, the metal complex has a maximum emission wavelength of 618 nm or more in the photoluminescence spectrum.

According to one embodiment of the present invention, in formula 1, at least one of X ₁ to X ₈ and Y ₁ to Y ₆ is selected from CR _x or CR _y , and R _x and R _y are each independently selected from deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted The alkyl group is selected from the group consisting of an 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, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxyl group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof.

In this embodiment, at least one of X ₁ to X ₈ and Y ₁ to Y ₆ is selected from CR _x or CR _y means that at least one of X ₁ to X ₈ is selected from CR _x , or at least one of Y ₁ to Y ₆ is selected from CR _y , and each occurrence of R _x and R _y is the same or different and selected from the non-hydrogen substituent group.

According to one embodiment of the present invention, in formula 1, at least two or three of X ₁ to X ₈ and Y ₁ to Y ₆ are selected from CR _x and/or CR _y , and R _x and R _y are each independently selected from deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted The alkyl group is selected from the group consisting of an 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, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxyl group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof.

In this embodiment, at least two or three of X ₁ to X ₈ and Y ₁ to Y ₆ are selected from CR _x and/or CR _y , including at least one or more of the following situations among X ₁ to X ₈ and Y ₁ to Y ₆ : (1) at least two of X ₁ to X ₈ are selected from CR _x ; (2) at least two of Y ₁ to Y ₆ are selected from CR _y ; (3) at least two of X ₁ to X ₈ are selected from CR _x , and at least one of Y ₁ to Y ₆ is selected from CR _y ; (4) at least one of X ₁ to X ₈ are selected from CR _x , and at least two of Y ₁ to Y ₆ are selected from CR _y ; (5) at least three of X ₁ to X ₈ are selected from CR _x . (6) at least three of Y ₁ to Y ₆ are selected from CR _y ; (7) at least one of X ₁ to X ₈ is selected from CR _x , and at least one of Y ₁ to Y ₆ is selected from CR _y . In any one of the above situations, R _x and R _y are the same or different at each occurrence and are selected from the non-hydrogen substituent group.

（Ｒ_１～Ｒ_７は、出現毎に同一または異なって水素、重水素、ハロゲン、置換または非置換の炭素原子数１～２０のアルキル基、置換または非置換の環炭素原子数３～２０のシクロアルキル基、置換または非置換の炭素原子数１～２０のヘテロアルキル基、置換または非置換の炭素原子数７～３０のアラルキル基、置換または非置換の炭素原子数１～２０のアルコキシ基、置換または非置換の炭素原子数６～３０のアリールオキシ基、置換または非置換の炭素原子数２～２０のアルケニル基、置換または非置換の炭素原子数６～３０のアリール基、置換または非置換の炭素原子数３～３０のヘテロアリール基、置換または非置換の炭素原子数３～２０のアルキルシリル基、置換または非置換の炭素原子数６～２０のアリールシリル基、置換または非置換の炭素原子数０～２０のアミン基、アシル基、カルボニル基、カルボキシル基、エステル基、シアノ基、イソシアノ基、ヒドロキシル基、スルファニル基、スルフィニル基、スルホニル基、ホスフィノ基、およびこれらの組合せからなる群から選ばれ、
好ましくは、Ｒ_１～Ｒ_３のうちの少なくとも１つまたは２つは、置換または非置換の炭素原子数１～２０のアルキル基、置換または非置換の環炭素原子数３～２０のシクロアルキル基、置換または非置換の炭素原子数１～２０のヘテロアルキル基、またはこれらの組合せから選ばれ、および／またはＲ_４～Ｒ_６のうちの少なくとも１つは、置換または非置換の炭素原子数１～２０のアルキル基、置換または非置換の環炭素原子数３～２０のシクロアルキル基、置換または非置換の炭素原子数１～２０のヘテロアルキル基、またはこれらの組合せであり、
より好ましくは、Ｒ_１～Ｒ_３のうちの少なくとも２つは、置換または非置換の炭素原子数２～２０のアルキル基、置換または非置換の環炭素原子数３～２０のシクロアルキル基、置換または非置換の炭素原子数２～２０のヘテロアルキル基、またはこれらの組合せから選ばれ、および／またはＲ_４～Ｒ_６のうちの少なくとも２つは、置換または非置換の炭素原子数２～２０のアルキル基、置換または非置換の環炭素原子数３～２０のシクロアルキル基、置換または非置換の炭素原子数２～２０のヘテロアルキル基、またはこれらの組合せから選ばれる。） According to an embodiment of the present invention, the metal complex further includes a ligand _Lb having a structure represented by the following formula:

(R ₁ to R ₇ each occurrence are the same or different and each occurrence is selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amine group, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxyl group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof;
Preferably, at least one or two of R ₁ to R ₃ are selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, or a combination thereof, and/or at least one of R ₄ to R ₆ is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, or a combination thereof;
More preferably, at least two of R ₁ to R ₃ are selected from a substituted or unsubstituted alkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 20 carbon atoms, or a combination thereof, and/or at least two of R ₄ to R ₆ are selected from a substituted or unsubstituted alkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 20 carbon atoms, or a combination thereof.

According to one embodiment of the present invention, in the formula 1, Y ₁ to Y ₆ are the same or different and selected from CR _y1 , CR _y2 or N, and at least one of Y ₁ to Y ₆ is selected from CR _y2 , and R _y2 has a structure of -L-SiR _s1 R _s2 R _s3 ;
R _y1 , R _s1 , R _s2 and R _s3 each occur the same or different and each represent 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 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 hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
L is selected from the group consisting of a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;
Adjacent substituents R _s1 , R _s2 and R _s3 may be bonded to form a ring.

In this embodiment, the fact that adjacent substituents _Rs1 , _Rs2 , and _Rs3 may be bonded to form a ring means that adjacent substituent groups, for example, the substituents _Rs1 and _Rs2 , the substituents _Rs1 and _Rs3 , and the substituents _Rs2 and _Rs3 may be bonded to one or more of the adjacent substituent groups to form a ring. Obviously, none of the substituent groups may be bonded to form a ring.

According to one embodiment of the present invention, in formula 1, Y ₁ to Y ₆ are selected from CR _y1 , CR _y2 or N, each occurrence being the same or different, and at least one of Y ₁ to Y ₆ is selected from CR _y1 , and R _y1 is fluorine.

According to one embodiment of the present invention, in formula 1, at least one of Y ₂ to Y ₆ is selected from CR _y1 , and R _y1 is fluorine.

（Ｚは、Ｏ、ＳまたはＳｅから選ばれ、
Ｘ_１～Ｘ_８は、出現毎に同一または異なってＣ、ＣＲ_ｘまたはＮから選ばれ、
Ｙ_１～Ｙ_６は、出現毎に同一または異なってＣＲ_ｙ１、ＣＲ_ｙ２またはＮから選ばれ、且つＹ_１～Ｙ_６のうちの少なくとも１つは、ＣＲ_ｙ２から選ばれ、前記Ｒ_ｙ２は、－Ｌ－ＳｉＲ_ｓ１Ｒ_ｓ２Ｒ_ｓ３の構造を有し、
Ｒ_ｘ、Ｒ_ｙ１、Ｒ_ｓ１、Ｒ_ｓ２、Ｒ_ｓ３は、出現毎に同一または異なって水素、重水素、ハロゲン、置換または非置換の炭素原子数１～２０のアルキル基、置換または非置換の環炭素原子数３～２０のシクロアルキル基、置換または非置換の炭素原子数１～２０のヘテロアルキル基、置換または非置換の炭素原子数７～３０のアラルキル基、置換または非置換の炭素原子数１～２０のアルコキシ基、置換または非置換の炭素原子数６～３０のアリールオキシ基、置換または非置換の炭素原子数２～２０のアルケニル基、置換または非置換の炭素原子数６～３０のアリール基、置換または非置換の炭素原子数３～３０のヘテロアリール基、置換または非置換の炭素原子数３～２０のアルキルシリル基、置換または非置換の炭素原子数６～２０のアリールシリル基、置換または非置換の炭素原子数０～２０のアミン基、アシル基、カルボニル基、カルボキシル基、エステル基、シアノ基、イソシアノ基、ヒドロキシル基、スルファニル基、スルフィニル基、スルホニル基、ホスフィノ基、およびこれらの組合せからなる群から選ばれ、
Ｌは、単結合、置換または非置換の炭素原子数１～２０のアルキレン基、置換または非置換の炭素原子数３～２０のシクロアルキレン基、置換または非置換の炭素原子数６～２０のアリーレン基、置換または非置換の炭素原子数３～２０のヘテロアリーレン基、またはこれらの組合せからなる群から選ばれ、
隣り合う置換基Ｒ_ｘ、Ｒ_ｓ１、Ｒ_ｓ２、Ｒ_ｓ３は、結合して環を形成していてもよい。） According to one embodiment of the present invention, a metal complex is disclosed, the metal in the metal complex being selected from metals having a relative atomic mass greater than 40, and comprising a ligand L _a having a structure represented by Formula 1′.

Z is selected from O, S or Se;
X ₁ to X ₈ are each identically or differently selected from C, CR _x or N;
Y ₁ to Y ₆ are each the same or different and selected from CR _y1 , CR _y2 or N, and at least one of Y ₁ to Y ₆ is selected from CR _y2 , said R _y2 having the structure -L-SiR _s1 R _s2 R _s3 ;
R _x , R _y1 , R _s1 , R _s2 and R _s3 each occur the same or different and each represent 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 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 hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
L is selected from the group consisting of a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;
Adjacent substituents R _x , R _s1 , R _s2 and R _s3 may be bonded to form a ring.

In the present specification, "adjacent substituents R _x , R _s1 , R _s2 , and R _s3 may be bonded to form a ring" means that adjacent substituent groups, for example, two substituents R _x , two substituents R _s1 and R _s2 , two substituents R _s1 and R _s3 , and two substituents R _s2 and R _s3 , may be bonded to form a ring by any one or more of the adjacent substituent groups. Obviously, the substituent groups may not be bonded to form a ring. Any adjacent substituents R _y1 may not be bonded to form a ring.

According to one embodiment of the present invention, in the formula 1 or formula 1', two adjacent ones of X ₁ to X ₄ are C, and one of the C is bonded to the metal by a carbon-metal bond, and one of X ₁ to X ₄ adjacent to the carbon-metal bond is selected from CR _x , and the R _x is deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted 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 carbon the alkyl group having from 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having from 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having from 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having from 6 to 20 carbon atoms, a substituted or unsubstituted amine group, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxyl group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof.

の構造を有する。その際に、Ｘ_１～Ｘ_４のうちの前記炭素－金属結合に隣接する１つは、Ｘ_３を指す。Ｘ_３は、ＣＲ_ｘから選ばれ、且つ前記Ｒ_ｘは、前記置換基グループから選ばれる。ただし、たとえば、前記式１中、Ｘ_２がＣであり、Ｘ_１もＣであり、金属と炭素－金属結合を形成する場合、前記Ｌ_ａは、

の構造を有し、Ｘ_１～Ｘ_４のうち、置換可能な前記炭素－金属結合の隣接位置が存在せず、明らかに本実施例に含まれる情況ではない。 In this embodiment, two adjacent ones of X ₁ to X ₄ are C, one of the C is bonded to the metal by a carbon-metal bond, and at that time, one of X ₁ to X ₄ adjacent to the carbon-metal bond is selected from CR _x , and the R _x is selected from the substituent group. For example, when the X ₁ is C and the X ₂ is also C and forms a carbon-metal bond with the metal, the L _a is

In this case, one of X ₁ to X ₄ adjacent to the carbon-metal bond is X _3. X ₃ is selected from CR _x , and the R _x is selected from the above-mentioned substituent group. However, for example, in the above-mentioned formula 1, when X ₂ is C and X ₁ is also C and forms a carbon-metal bond with a metal, the L _a is

Among X ₁ to X ₄ , there is no adjacent position of the carbon-metal bond that can be replaced, and this is obviously not included in this embodiment.

According to one embodiment of the present invention, in formula 1', at least one of X ₁ to X ₈ and Y ₁ to Y ₆ is selected from CR _x or CR _y1 , and R _x and R _y1 are each independently selected from deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amine group, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxyl group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof.

In this embodiment, at least one of X ₁ to X ₈ and Y ₁ to Y ₆ is selected from CR _x or CR _y1 means that at least one of X ₁ to X ₈ is selected from CR _x , or at least one of Y ₁ to Y ₆ is selected from CR _y1 , and each occurrence of R _x and R _y1 is the same or different and selected from the non-hydrogen substituent group.

According to one embodiment of the present invention, in formula 1', at least two or three of X ₁ to X ₈ and Y ₁ to Y ₆ are selected from CR _x or CR _y1 , and R _x and R _y1 are each independently selected from deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amine group, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxyl group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof.

In this embodiment, at least two or three of X ₁ to X ₈ and Y ₁ to Y ₆ are selected from CR _x and/or CR _y1 , which includes at least one or more of the following situations among X ₁ to X ₈ and Y ₁ to Y ₆ : (1) at least two of X ₁ to X ₈ are selected from CR _x ; (2) at least two of Y ₁ to Y ₆ are selected from CR _y1 ; (3) at least two of X ₁ to X ₈ are selected from CR _x , and at least one of Y ₁ to Y ₆ is selected from CR _y1 ; (4) at least one of X ₁ to X ₈ are selected from CR _x , and at least two of Y ₁ to Y ₆ are selected from CR _y1 ; (5) at least three of X ₁ to X ₈ are selected from CR _x . (6) at least three of Y ₁ to Y ₆ are selected from CR _y1 . (7) at least one of X ₁ to X ₈ is selected from CR _x , and at least one of Y ₁ to Y ₆ is selected from CR _y1 . In any one of the above situations, R _x and R _y1 are each the same or different and selected from the non-hydrogen substituent group.

According to one embodiment of the present invention, in the formula 1 or formula 1', _X7 is selected from _CRx or N, and _Rx is 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, 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 ... ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 ring 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 heteroalkyl group having 1 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 and a substituted or unsubstituted aryl group having from 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having from 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having from 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having from 6 to 20 carbon atoms, a substituted or unsubstituted amine group having from 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

（Ｚは、Ｏ、ＳまたはＳｅから選ばれ、
Ｘ_３～Ｘ_８は、出現毎に同一または異なってＣＲ_ｘまたはＮから選ばれ、
Ｙ_１～Ｙ_６は、出現毎に同一または異なってＣＲ_ｙ１、ＣＲ_ｙ２またはＮから選ばれ、且つＹ_１～Ｙ_６のうちの少なくとも１つは、ＣＲ_ｙ２から選ばれ、前記Ｒ_ｙ２は、－Ｌ－ＳｉＲ_ｓ１Ｒ_ｓ２Ｒ_ｓ３の構造を有し、
Ｒ_ｘ、Ｒ_ｙ１、Ｒ_ｓ１、Ｒ_ｓ２、Ｒ_ｓ３は、出現毎に同一または異なって水素、重水素、ハロゲン、置換または非置換の炭素原子数１～２０のアルキル基、置換または非置換の環炭素原子数３～２０のシクロアルキル基、置換または非置換の炭素原子数１～２０のヘテロアルキル基、置換または非置換の炭素原子数７～３０のアラルキル基、置換または非置換の炭素原子数１～２０のアルコキシ基、置換または非置換の炭素原子数６～３０のアリールオキシ基、置換または非置換の炭素原子数２～２０のアルケニル基、置換または非置換の炭素原子数６～３０のアリール基、置換または非置換の炭素原子数３～３０のヘテロアリール基、置換または非置換の炭素原子数３～２０のアルキルシリル基、置換または非置換の炭素原子数６～２０のアリールシリル基、置換または非置換の炭素原子数０～２０のアミン基、アシル基、カルボニル基、カルボキシル基、エステル基、シアノ基、イソシアノ基、ヒドロキシル基、スルファニル基、スルフィニル基、スルホニル基、ホスフィノ基、およびこれらの組合せからなる群から選ばれ、
Ｌは、単結合、置換または非置換の炭素原子数１～２０のアルキレン基、置換または非置換の炭素原子数３～２０のシクロアルキレン基、置換または非置換の炭素原子数６～２０のアリーレン基、置換または非置換の炭素原子数３～２０のヘテロアリーレン基、またはこれらの組合せからなる群から選ばれ、
隣り合う置換基Ｒ_ｘ、Ｒ_ｓ１、Ｒ_ｓ２、Ｒ_ｓ３は、結合して環を形成していてもよい。） According to one embodiment of the present invention, L _a has a structure represented by Formula 2:

Z is selected from O, S or Se;
X ₃ to X ₈ are each identically or differently selected from CR _x or N at each occurrence;
Y ₁ to Y ₆ are each the same or different and selected from CR _y1 , CR _y2 or N, and at least one of Y ₁ to Y ₆ is selected from CR _y2 , said R _y2 having the structure -L-SiR _s1 R _s2 R _s3 ;
R _x , R _y1 , R _s1 , R _s2 and R _s3 each occur the same or different and each represent 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 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 hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
L is selected from the group consisting of a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;
Adjacent substituents R _x , R _s1 , R _s2 and R _s3 may be bonded to form a ring.

According to one embodiment of the present invention, Y ₁ to Y ₂ are selected from CR _y1 or N, each occurrence being the same or different; Y ₃ to Y ₆ are selected from CR _y1 , CR _y2 or N, each occurrence being the same or different; and at least one of Y ₃ to Y ₆ is selected from CR _y2 , said R _y2 having the structure -L-SiR _s1 R _s2 R _s3 ;
R _y1 is, each occurrence being the same or different, selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted 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 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 hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
R _s1 , R _s2 and R _s3 each occurrence are the same or different and each occurrence 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 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 hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
L is selected from the group consisting of a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;
Adjacent substituents R _s1 , R _s2 and R _s3 may be bonded to form a ring.

In this specification, "adjacent substituents R _s1 , R _s2 , and R _s3 may be bonded to form a ring" means that adjacent substituent groups, for example, the substituents R _s1 and R _s2 , the substituents R _s1 and R _s3 , and the substituents R _s2 and R _s3 , may be bonded to one or more of the adjacent substituent groups to form a ring. Obviously, the substituent groups do not have to be bonded to form a ring. Any adjacent substituents R _y1 cannot be bonded to form a ring.

According to one embodiment of the present invention, Y ₁ to Y ₂ are identically or differently selected from CR _y1 or N at each occurrence, and R Each occurrence of _y1 may be the same or different and is selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted 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 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 hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof. The expression _"y1" being selected from the group consisting of a substituted alkyl group, a substituted cycloalkyl group, a substituted heteroalkyl group, a substituted aralkyl group, a substituted alkoxy group, a substituted aryloxy group, a substituted alkenyl group, a substituted aryl group, a substituted heteroaryl group, a substituted amino group, a substituted acyl group, a substituted carbonyl group, a substituted carboxyl group, a substituted ester group, a substituted sulfinyl group, a substituted sulfonyl group, and a substituted phosphino group means that any one of the alkyl group, the cycloalkyl group, the heteroalkyl group, the aralkyl group, the alkoxy group, the aryloxy group, the alkenyl group, the aryl group, the heteroaryl group, the amino group, the acyl group, the carbonyl group, the carboxyl group, the ester group, the sulfinyl group, the sulfonyl group, and the phosphino group is selected from the group consisting of a deuterium atom, a halogen atom, an unsubstituted carbon atom, a substituted aryloxy group, an alkenyl group, an aryl group, a heteroaryl group, an amino group, an acyl group, a carbonyl group, a carboxyl group, an ester group, a sulfinyl group, a sulfonyl group, and a phosphino group. It means that the group may be substituted with one or more groups selected from an alkyl group having 1 to 20 atoms, an unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, an unsubstituted heteroalkyl group having 1 to 20 carbon atoms, an unsubstituted aralkyl group having 7 to 30 carbon atoms, an unsubstituted alkoxy group having 1 to 20 carbon atoms, an unsubstituted aryloxy group having 6 to 30 carbon atoms, an unsubstituted alkenyl group having 2 to 20 carbon atoms, an unsubstituted alkynyl group having 2 to 20 carbon atoms, an unsubstituted aryl group having 6 to 30 carbon atoms, an unsubstituted heteroaryl group having 3 to 30 carbon atoms, an unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

According to one embodiment of the present invention, R _s1 , R _s2 and R _s3 are each independently selected from hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted 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 ... 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 hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
Adjacent substituents R _s1 , R _s2 and R _s3 may be bonded to form a ring.

According to one embodiment of the present invention, Y ₁ to Y ₂ are selected from CR _y1 or N, each occurrence being the same or different; Y ₃ to Y ₆ are selected from CR _y1 , CR _y2 or N, each occurrence being the same or different; and at least one of Y ₃ to Y ₆ is selected from CR _y2 , said R _y2 having the structure -L-SiR _s1 R _s2 R _s3 ;
R _y1 is, each occurrence being the same or different, selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted 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 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 hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
R _s1 , R _s2 and R _s3 each appearing the same or differently are selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted 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, and combinations thereof;
L is selected from the group consisting of a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;
Adjacent substituents R _s1 , R _s2 and R _s3 may be bonded to form a ring.

Ｒ_ａ、Ｒ_ｂおよびＲ_ｃは、出現毎に同一または異なって一置換、複数置換、または無置換を表し、
Ｘ_ｂは、出現毎に同一または異なってＯ、Ｓ、Ｓｅ、ＮＲ_Ｎ１およびＣＲ_Ｃ１Ｒ_Ｃ２からなる群から選ばれ、
Ｘ_ｃおよびＸ_ｄは、出現毎に同一または異なってＯ、Ｓ、ＳｅおよびＮＲ_Ｎ２からなる群から選ばれ、
Ｒ_ａ、Ｒ_ｂ、Ｒ_ｃ、Ｒ_Ｎ１、Ｒ_Ｎ２、Ｒ_Ｃ１およびＲ_Ｃ２は、出現毎に同一または異なって水素、重水素、ハロゲン、置換または非置換の炭素原子数１～２０のアルキル基、置換または非置換の環炭素原子数３～２０のシクロアルキル基、置換または非置換の炭素原子数１～２０のヘテロアルキル基、置換または非置換の炭素原子数７～３０のアラルキル基、置換または非置換の炭素原子数１～２０のアルコキシ基、置換または非置換の炭素原子数６～３０のアリールオキシ基、置換または非置換の炭素原子数２～２０のアルケニル基、置換または非置換の炭素原子数６～３０のアリール基、置換または非置換の炭素原子数３～３０のヘテロアリール基、置換または非置換の炭素原子数３～２０のアルキルシリル基、置換または非置換の炭素原子数６～２０のアリールシリル基、置換または非置換の炭素原子数０～２０のアミン基、アシル基、カルボニル基、カルボキシル基、エステル基、シアノ基、イソシアノ基、ヒドロキシル基、スルファニル基、スルフィニル基、スルホニル基、ホスフィノ基、およびこれらの組合せからなる群から選ばれ、
隣り合う置換基Ｒ_ａ、Ｒ_ｂ、Ｒ_ｃ、Ｒ_Ｎ１、Ｒ_Ｎ２、Ｒ_Ｃ１およびＲ_Ｃ２は、結合して環を形成していてもよい。 According to one embodiment of the present invention, the metal complex has a structure of M(L _a ) _m (L _b ) _n (L _c ) _q ;
the metal M is selected from Ir, Rh, Re, Os, Pt, Au or Cu, preferably the metal M is selected from Ir, Pt or Os;
L _a , L _b and L _c are the first, second and third ligands of said complex, respectively; m is selected from 1, 2 or 3; n is selected from 0, 1 or 2; q is selected from 0, 1 or 2;
and m+n+q is equal to the oxidation state of the metal M, and when m is greater than 1, the L _a 's are the same or different, when n is 2, the two L _b 's are the same or different, when q is 2, the two L _c 's are the same or different,
L _a , L _b and L _c may be bonded to form a multidentate ligand, for example, any two of L _a , L _b and L _c may be bonded to form a tetradentate ligand, or, for example, L _a , L _b and L _c may be bonded to each other to form a hexadentate ligand;
L _b and L _c each occur the same or different and are selected from the group consisting of the following structures:

R _a , R _b and R _c are the same or different and each occurrence represents mono-, poly- or no substitution;
X _b is, at each occurrence, the same or different, selected from the group consisting of O, S, Se, NR _N1 and CR _C1 R _C2 ;
_Xc and _Xd , each occurrence, are the same or different and are selected from the group consisting of O, S, Se and NR _N2 ;
R _a , R _b , R _c , R _N1 , R _N2 , R _C1 and R _C2 are, each occurrence, the same or different and each represent 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 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 hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
Adjacent substituents _R.sup.a , _R.sup.b , _R.sup.c , _R.sup.N1 , _R.sup.N2 , _R.sup.C1 and _R.sup.C2 may be bonded to form a ring.

In this embodiment, adjacent substituents R _a , R _b , R _c , R _N1 , R _N2 , R _C1 and R _C2 may be bonded to form a ring, which means that adjacent substituent groups, for example, two substituents R _a , two substituents R _b , two substituents R _c , substituents R _a and R _b , substituents R _a and R _c , substituents R _b and R _c , substituents R _a and R _N1 , substituents R _b and R _N1 , substituents R _a and R _C1 , substituents R _a and R _C2 , substituents R _b and R _C1 , substituents R _b and R _C2 , substituents R _a and R _N2 , substituents R _b and R _N2 , and R _C1 and R _C2 , may be bonded to form a ring. Obviously, the substituents do not have to be linked to form a ring.

Ｘ_ｃおよびＸ_ｄは、出現毎に同一または異なってＯ、Ｓ、ＳｅおよびＮＲ_Ｎ２からなる群から選ばれ、
Ｒ_ａ１、Ｒ_ｂ１、Ｒ_ｃ１、Ｒ_Ｎ２は、出現毎に同一または異なって水素、重水素、ハロゲン、置換または非置換の炭素原子数１～２０のアルキル基、置換または非置換の環炭素原子数３～２０のシクロアルキル基、置換または非置換の炭素原子数１～２０のヘテロアルキル基、置換または非置換の炭素原子数７～３０のアラルキル基、置換または非置換の炭素原子数１～２０のアルコキシ基、置換または非置換の炭素原子数６～３０のアリールオキシ基、置換または非置換の炭素原子数２～２０のアルケニル基、置換または非置換の炭素原子数６～３０のアリール基、置換または非置換の炭素原子数３～３０のヘテロアリール基、置換または非置換の炭素原子数３～２０のアルキルシリル基、置換または非置換の炭素原子数６～２０のアリールシリル基、置換または非置換の炭素原子数０～２０のアミン基、アシル基、カルボニル基、カルボキシル基、エステル基、シアノ基、イソシアノ基、ヒドロキシル基、スルファニル基、スルフィニル基、スルホニル基、ホスフィノ基、およびこれらの組合せからなる群から選ばれ、
隣り合う置換基Ｒ_ａ１、Ｒ_ｂ１、Ｒ_ｃ１は、結合して環を形成していてもよく、
Ｌ_ｃは、出現毎に同一または異なって以下の構造からなる群から選ばれ、

Ｒ_ａ、Ｒ_ｂ、Ｒ_ｃは、出現毎に同一または異なって一置換、複数置換、または無置換を表し、
Ｘ_ｅは、出現毎に同一または異なってＯ、Ｓ、ＳｅおよびＮＲ_Ｎ３からなる群から選ばれ、
Ｒ_ａ、Ｒ_ｂ、Ｒ_ｃ、Ｒ_Ｎ３は、出現毎に同一または異なって水素、重水素、ハロゲン、置換または非置換の炭素原子数１～２０のアルキル基、置換または非置換の環炭素原子数３～２０のシクロアルキル基、置換または非置換の炭素原子数１～２０のヘテロアルキル基、置換または非置換の炭素原子数７～３０のアラルキル基、置換または非置換の炭素原子数１～２０のアルコキシ基、置換または非置換の炭素原子数６～３０のアリールオキシ基、置換または非置換の炭素原子数２～２０のアルケニル基、置換または非置換の炭素原子数６～３０のアリール基、置換または非置換の炭素原子数３～３０のヘテロアリール基、置換または非置換の炭素原子数３～２０のアルキルシリル基、置換または非置換の炭素原子数６～２０のアリールシリル基、置換または非置換の炭素原子数０～２０のアミン基、アシル基、カルボニル基、カルボキシル基、エステル基、シアノ基、イソシアノ基、ヒドロキシル基、スルファニル基、スルフィニル基、スルホニル基、ホスフィノ基、およびこれらの組合せからなる群から選ばれ、
隣り合う置換基Ｒ_ｂ、Ｒ_ｃは、結合して環を形成していてもよい。 According to one embodiment of the present invention, the metal complex has a structure of M(L _a ) _m (L _b ) _n (L _c ) _q ;
the metal M is selected from Ir, Rh, Re, Os, Pt, Au or Cu;
L _a , L _b and L _c are respectively the first, second and third ligands of said complex, m is selected from 1, 2 or 3, n is selected from 0, 1 or 2, q is selected from 0, 1 or 2;
and m+n+q is equal to the oxidation state of the metal M, and when m is greater than 1, the multiple L _a 's may be the same or different, when n is 2, the two L _b 's may be the same or different, when q is 2, the two L _c 's may be the same or different, and L _a , L _b and L _c may be bonded to form a multidentate ligand;
L _b is selected from the following structures, each occurrence being the same or different:

_Xc and _Xd , each occurrence, are the same or different and are selected from the group consisting of O, S, Se and NR _N2 ;
R _a1 , R _b1 , R _c1 and R _N2 each occurrence are the same or different and each represent 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 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 hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
adjacent substituents R _a1 , R _b1 and R _c1 may be bonded to form a ring;
_Lc , each occurrence being the same or different, is selected from the group consisting of the following structures:

R _a , R _b , and R _c are the same or different and each occurrence represents mono-substitution, multi-substitution, or no substitution;
_Xe , at each occurrence, is the same or different and is selected from the group consisting of O, S, Se and NR _N3 ;
R _a , R _b , R _c , and R _N3 each occurrence are the same or different and each represent 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 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 hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
Adjacent substituents R _b and R _c may be bonded to form a ring.

In this embodiment, "adjacent substituents R _a1 , R _b1 , and R _c1 may be bonded to form a ring" means that the substituents R _a1 and R _c1 or the substituents R _b1 and R _c1 may be bonded to form a ring. Obviously, the substituents R _a1 and R _c1 or the substituents R _b1 and R _c1 do not have to be bonded to form a ring.

In this embodiment, "adjacent substituents R _b and R _c may be bonded to form a ring" means that when multiple substituents R _b and multiple substituents R _c are present, adjacent substituents R _b or adjacent substituents R _c may be bonded to form a ring. Obviously, when multiple substituents R _b and multiple substituents R _c are present, adjacent substituents R _b or adjacent substituents R _c do not have to be bonded to form a ring.

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

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

（ｍは、１または２であり、
Ｚは、出現毎に同一または異なってＯまたはＳから選ばれ、
Ｘ_３～Ｘ_８は、出現毎に同一または異なってＣＲ_ｘまたはＮから選ばれ、
Ｙ_１～Ｙ_６は、出現毎に同一または異なってＣＲ_ｙ１、ＣＲ_ｙ２またはＮから選ばれ、且つＹ_１～Ｙ_６のうちの少なくとも１つはＣＲ_ｙ２から選ばれ、前記Ｒ_ｙ２は、－Ｌ－ＳｉＲ_ｓ１Ｒ_ｓ２Ｒ_ｓ３の構造を有し、
Ｒ_ｘ、Ｒ_ｙ１、Ｒ_ｓ１、Ｒ_ｓ２、Ｒ_ｓ３、Ｒ_１、Ｒ_２、Ｒ_３、Ｒ_４、Ｒ_５、Ｒ_６、Ｒ_７は、出現毎に同一または異なって水素、重水素、ハロゲン、置換または非置換の炭素原子数１～２０のアルキル基、置換または非置換の環炭素原子数３～２０のシクロアルキル基、置換または非置換の炭素原子数１～２０のヘテロアルキル基、置換または非置換の炭素原子数７～３０のアラルキル基、置換または非置換の炭素原子数１～２０のアルコキシ基、置換または非置換の炭素原子数６～３０のアリールオキシ基、置換または非置換の炭素原子数２～２０のアルケニル基、置換または非置換の炭素原子数６～３０のアリール基、置換または非置換の炭素原子数３～３０のヘテロアリール基、置換または非置換の炭素原子数３～２０のアルキルシリル基、置換または非置換の炭素原子数６～２０のアリールシリル基、置換または非置換の炭素原子数０～２０のアミン基、アシル基、カルボニル基、カルボキシル基、エステル基、シアノ基、イソシアノ基、ヒドロキシル基、スルファニル基、スルフィニル基、スルホニル基、ホスフィノ基、およびこれらの組合せからなる群から選ばれ、
Ｌは、単結合、置換または非置換の炭素原子数１～２０のアルキレン基、置換または非置換の炭素原子数３～２０のシクロアルキレン基、置換または非置換の炭素原子数６～２０のアリーレン基、置換または非置換の炭素原子数３～２０のヘテロアリーレン基、またはこれらの組合せからなる群から選ばれ、
隣り合う置換基Ｒ_ｘ、Ｒ_ｓ１、Ｒ_ｓ２、Ｒ_ｓ３は、結合して環を形成していてもよく、
隣り合う置換基Ｒ_１、Ｒ_２、Ｒ_３、Ｒ_４、Ｒ_５、Ｒ_６、Ｒ_７は、結合して環を形成していてもよい。） According to one embodiment of the present invention, the metal complex has a structure represented by Formula 3:

m is 1 or 2,
Z, at each occurrence, is identically or differently selected from O or S;
X ₃ to X ₈ are each identically or differently selected from CR _x or N at each occurrence;
Y ₁ to Y ₆ are each the same or different and selected from CR _y1 , CR _y2 or N, and at least one of Y ₁ to Y ₆ is selected from CR _y2 , said R _y2 having the structure -L-SiR _s1 R _s2 R _s3 ;
R _x , R _y1 , R _s1 , R _s2 , R _s3 , R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ and R ₇ are each the same or different and each 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 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, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxyl group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof;
L is selected from the group consisting of a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;
adjacent substituents R _x , R _s1 , R _s2 and R _s3 may be bonded to form a ring;
Adjacent substituents R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , and R ₇ may be bonded to form a ring.

In this embodiment, the fact that adjacent substituents R _x , R _s1 , R _s2 , and R _s3 may be bonded to form a ring means that adjacent substituent groups, for example, two substituents R _x , two substituents R _s1 and R _s2 , two substituents R _s1 and R _s3 , and two substituents R _s2 and R _s3 , may be bonded to form a ring by any one or more of these substituent groups. Obviously, these substituent groups do not have to be bonded to form a ring.

In this embodiment, adjacent substituents R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , and R ₇ may be bonded to form a ring, which means that adjacent substituent groups, such as the substituents R ₁ and R ₂ , the substituents R ₁ and R ₃ , the substituents R ₂ and R ₃ , the substituents R ₄ and R ₅ , the substituents R ₅ and R ₆ , the substituents R ₄ and R ₆ , the substituents R ₁ and R ₇ , the substituents R ₂ and R ₇ , the substituents R ₃ and R ₇ , the substituents R ₄ and R ₇ , the substituents R ₅ and R ₇ , and the substituents R ₆ and R ₇ , may be bonded to form a ring by any one or more of the substituent groups. Obviously, the substituent groups do not have to be bonded to form a ring.

（ｍは、１または２であり、
Ｚは、出現毎に同一または異なってＯまたはＳから選ばれ、
Ｒ_１～Ｒ_７は、出現毎に同一または異なって水素、重水素、ハロゲン、置換または非置換の炭素原子数１～２０のアルキル基、置換または非置換の環炭素原子数３～２０のシクロアルキル基、置換または非置換の炭素原子数１～２０のヘテロアルキル基、置換または非置換の炭素原子数７～３０のアラルキル基、置換または非置換の炭素原子数１～２０のアルコキシ基、置換または非置換の炭素原子数６～３０のアリールオキシ基、置換または非置換の炭素原子数２～２０のアルケニル基、置換または非置換の炭素原子数６～３０のアリール基、置換または非置換の炭素原子数３～３０のヘテロアリール基、置換または非置換の炭素原子数３～２０のアルキルシリル基、置換または非置換の炭素原子数６～２０のアリールシリル基、置換または非置換の炭素原子数０～２０のアミン基、アシル基、カルボニル基、カルボキシル基、エステル基、シアノ基、イソシアノ基、ヒドロキシル基、スルファニル基、スルフィニル基、スルホニル基、ホスフィノ基、およびこれらの組合せからなる群から選ばれる。） According to one embodiment of the present invention, the metal complex has a structure represented by Formula 3:

m is 1 or 2,
Z, at each occurrence, is identically or differently selected from O or S;
R ₁ to R ₇ each occurrence are the same or different and each represent a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amine groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof.

（ｍは、１または２であり、
Ｚは、出現毎に同一または異なってＯまたはＳから選ばれ、
Ｒ_１～Ｒ_３のうちの少なくとも１つは、置換または非置換の炭素原子数１～２０のアルキル基、置換または非置換の環炭素原子数３～２０のシクロアルキル基、置換または非置換の炭素原子数１～２０のヘテロアルキル基、またはこれらの組合せから選ばれ、および／またはＲ_４～Ｒ_６のうちの少なくとも１つは、置換または非置換の炭素原子数１～２０のアルキル基、置換または非置換の環炭素原子数３～２０のシクロアルキル基、置換または非置換の炭素原子数１～２０のヘテロアルキル基、またはこれらの組合せである。） According to one embodiment of the present invention, the metal complex has a structure represented by Formula 3:

m is 1 or 2,
Z, at each occurrence, is identically or differently selected from O or S;
At least one of R ₁ to R ₃ is selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, or a combination thereof, and/or at least one of R ₄ to R ₆ is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, or a combination thereof.

（ｍは、１または２であり、
Ｚは、出現毎に同一または異なってＯまたはＳから選ばれ、
Ｒ_１～Ｒ_３のうちの少なくとも２つは、置換または非置換の炭素原子数１～２０のアルキル基、置換または非置換の環炭素原子数３～２０のシクロアルキル基、置換または非置換の炭素原子数１～２０のヘテロアルキル基、またはこれらの組合せから選ばれ、および／またはＲ_４～Ｒ_６のうちの少なくとも１つは、置換または非置換の炭素原子数１～２０のアルキル基、置換または非置換の環炭素原子数３～２０のシクロアルキル基、置換または非置換の炭素原子数１～２０のヘテロアルキル基、またはこれらの組合せである。） According to one embodiment of the present invention, the metal complex has a structure represented by Formula 3:

m is 1 or 2,
Z, at each occurrence, is identically or differently selected from O or S;
At least two of R ₁ to R ₃ are selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, or a combination thereof, and/or at least one of R ₄ to R ₆ is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, or a combination thereof.

（ｍは、１または２であり、
Ｚは、出現毎に同一または異なってＯまたはＳから選ばれ、
Ｒ_１～Ｒ_３のうちの少なくとも２つは、置換または非置換の炭素原子数２～２０のアルキル基、置換または非置換の環炭素原子数３～２０のシクロアルキル基、置換または非置換の炭素原子数２～２０のヘテロアルキル基、またはこれらの組合せから選ばれ、および／またはＲ_４～Ｒ_６のうちの少なくとも２つは、置換または非置換の炭素原子数２～２０のアルキル基、置換または非置換の環炭素原子数３～２０のシクロアルキル基、置換または非置換の炭素原子数２～２０のヘテロアルキル基、またはこれらの組合せである。） According to one embodiment of the present invention, the metal complex has a structure represented by Formula 3:

m is 1 or 2,
Z, at each occurrence, is identically or differently selected from O or S;
At least two of R ₁ to R ₃ are selected from a substituted or unsubstituted alkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 20 carbon atoms, or a combination thereof, and/or at least two of R ₄ to R ₆ are a substituted or unsubstituted alkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 20 carbon atoms, or a combination thereof.

According to one embodiment of the present invention, in formula 2 and/or formula 3, Y ₁ to Y ₆ are each independently selected from CR _y1 or CR _y2 .

According to one embodiment of the present invention, in formula 2 and/or formula 3, at least one of Y ₁ to Y ₆ is selected from N.

According to one embodiment of the present invention, in formula 2 and/or formula 3, Z is selected from O.

According to one embodiment of the present invention, in formula 2 and/or formula 3, at least one of X ₃ to X ₈ is selected from N.

According to one embodiment of the present invention, in formula 2 and/or formula 3, one of X ₃ to X ₈ is selected from N.

According to one embodiment of the present invention, in formula 2 and/or formula 3, X ₈ is N.

According to one embodiment of the present invention, in formula 2 and/or formula 3, X ₃ to X ₈ are each independently selected from CR _x .

According to one embodiment of the present invention, in Formula 2 and/or Formula 3, X ₃ to X ₈ are each independently selected from CR _x , and R _x is selected from hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a cyano group, or a combination thereof.

According to one embodiment of the present invention, in Formula 2 and/or Formula 3, X ₃ to X ₈ are each independently selected from CR _x , where R _x is selected from the group consisting of hydrogen, deuterium, fluorine, methyl, ethyl, isopropyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, norbornyl, adamantyl, trimethylsilyl, isopropyldimethylsilyl, phenyldimethylsilyl, trifluoromethyl, cyano, and combinations thereof.

According to one embodiment of the present invention, in formula 2 and/or formula 3, _X3 is _CRx , and said _Rx is selected from hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a cyano group, or a combination thereof.

According to one embodiment of the present invention, in Formula 2 and/or Formula 3, _X3 is selected from _CRx , and _Rx is selected from deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a cyano group, or a combination thereof.

According to one embodiment of the present invention, in formula 2 and/or formula 3, X ₃ is selected from CR _x , and R _x is selected from a methyl group or a deuterated methyl group.

According to one embodiment of the present invention, _Y2 is selected from _CRy1 or _CRy2 , _Ry1 is selected from the group consisting of substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, and combinations thereof, _Ry2 has a structure of -L- _SiRs1Rs2Rs3 , _Rs1 , _Rs2 , _Rs3 are each independently selected from the group consisting of substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, _and combinations thereof. _s3 may be the same or different at each occurrence and is 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 aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 3 to 20 carbon atoms, L is selected from the group consisting of a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;
Adjacent substituents R _s1 , R _s2 and R _s3 may be bonded to form a ring.

According to one embodiment of the present invention, in formula 2 and/or formula 3, at least one of Y ₁ to Y ₆ is selected from CR _y2 , R _y2 has a structure of -L-SiR _s1 R _s2 R _s3 , L is selected from a single bond, and R _s1 , R _s2 and R _s3 are each independently selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and combinations thereof.

According to one embodiment of the present invention, in formula 2 and/or formula 3, _Y2 and/or _Y4 are selected from _CRy2 , _Ry2 has a structure of -L- _SiRs1Rs2Rs3 , L is selected from a single bond, _Rs1 , _Rs2 and _{Rs3 are} each independently selected from the _group consisting of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and combinations thereof, and at least one or two or three of _Rs1 , _Rs2 and _Rs3 are each independently selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or combinations thereof.

According to one embodiment of the present invention, in formula 2 and/or formula 3, at least one of Y ₁ to Y ₆ is selected from CR _y2 , R _y2 has a structure of -L-SiR _s1 R _s2 R _s3 , L is selected from a single bond, and R _s1 , R _s2 and R _s3 are each independently selected from the group consisting of a methyl group, an ethyl group, an isopropyl group, an isobutyl group, a tert-butyl group, a neopentyl group, a cyclopentyl group, a cyclopentylmethyl group, a cyclohexyl group, a norbornyl group, an adamantyl group, a trifluoromethyl group, a phenyl group, and combinations thereof.

According to one embodiment of the present invention, in formula 1 (or 1'), Y ₁ to Y ₆ are selected from CR _y (or CR _y1 ) or N, and R _y (or R _y1 ) is selected from hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted 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 and R y (or R y1 ) is selected from the group consisting of an 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 hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, _a phosphino group, and combinations thereof. When the substituent is selected from a substituted alkyl group having 1 to 20 carbon atoms, a substituted cycloalkyl group having 3 to 20 ring carbon atoms, or a substituted heteroalkyl group having 1 to 20 carbon atoms, the substituent is selected from hydrogen, deuterium, halogen, an unsubstituted alkyl group having 1 to 20 carbon atoms, an unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, an unsubstituted heteroalkyl group having 1 to 20 carbon atoms, an unsubstituted aralkyl group having 7 to 30 carbon atoms, an unsubstituted alkoxy group having 1 to 20 carbon atoms, an unsubstituted aryl group having 6 to 3 ... and the like. The alkyl group is selected from the group consisting of an unsubstituted aryl group having from 6 to 30 carbon atoms, an unsubstituted aryl group having from 3 to 30 carbon atoms, an unsubstituted alkylsilyl group having from 3 to 20 carbon atoms, an unsubstituted arylsilyl group having from 6 to 20 carbon atoms, an unsubstituted amine group having from 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

According to one embodiment of the present invention, in formula 1 or 1', X ₁ to X ₈ are each selected from C, CR _x or N, and R _x is each selected from hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 2 to 2 ...6 to 30 carbon atoms, and 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, acyl group, carbonyl group, carboxyl group, ester group, hydroxyl group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof.

According to one embodiment of the present invention, each occurrence of L _a is the same or different and is any one selected from the group consisting of L _a1 to L _a1539 . For specific structures of L _a1 to L _a1539 , please refer to claim 20.

中、
Ｌ_ａ１～Ｌ_ａ１２がその中に挙げられる構造から選ばれることを代表する。Ｌ_ａ１に対して、その構造における置換基Ｒ^ａがＨであり、Ｌ_ａ１の構造が

であることを示す。類似的には、Ｌ_ａ２に対して、その構造における置換基Ｒ^ａがＣＨ_３であり、Ｌ_ａ２の構造が

であることを示す。類似的には、Ｌ_ａ３に対して、その構造における置換基Ｒ^ａがＲ^ａ１であり、Ｒ^ａ１が

であり、Ｌ_ａ３の構造が

であることを示す。Ｌ_ａ４～Ｌ_{ａ１５０７}に対しても、同様である。 In this embodiment, each occurrence of L _a is the same or different and is any one selected from the group consisting of L _a1 to L _a1539 .
for example,

In,
L _a1 to L _a12 are representatively selected from the structures listed therein. For L _a1 , the substituent R ^a in the structure is H, and the structure of L _a1 is

Analogously, for L _a2 , the substituent R ^a in the structure is CH ₃ , and the structure of L _a2 is

Analogously, for L _a3 , the substituent R ^a in the structure is R ^a1 , and R ^a1 is

and the structure of L _a3 is

The same is true for L _a4 to L _a1507 .

According to an embodiment of the present invention, each occurrence of L _a is the same or different and is any one selected from the group consisting of L _a1 to L _a1611 . For specific structures of the L _a1 to L _a1611 , please refer to claim 20.

、
（Ｒ_１～Ｒ_７は、それぞれ独立して水素、重水素、ハロゲン、置換または非置換の炭素原子数１～２０のアルキル基、置換または非置換の環炭素原子数３～２０のシクロアルキル基、シアノ基、およびこれらの組合せからなる群から選ばれ、
隣り合う置換基Ｒ_１、Ｒ_２、Ｒ_３、Ｒ_４、Ｒ_５、Ｒ_６、Ｒ_７は、結合して環を形成していてもよい。） According to one embodiment of the present invention, L _b is selected from the following structures, which may be the same or different at each occurrence:

,
(R ₁ to R ₇ 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 cyano group, and combinations thereof;
Adjacent substituents R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , and R ₇ may be bonded to form a ring.

In this embodiment, adjacent substituents R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , and R ₇ may be bonded to form a ring, which means that adjacent substituent groups, such as the substituents R ₁ and R ₂ , the substituents R ₁ and R ₃ , the substituents R ₂ and R ₃ , the substituents R ₄ and R ₅ , the substituents R ₅ and R ₆ , the substituents R ₄ and R ₆ , the substituents R ₁ and R ₇ , the substituents R ₂ and R ₇ , the substituents R ₃ and R ₇ , the substituents R ₄ and R ₇ , the substituents R ₅ and R ₇ , and the substituents R ₆ and R ₇ , may be bonded to form a ring by at least one or more of the substituent groups. Obviously, the substituent groups do not have to be bonded to form a ring.

According to one embodiment of the present invention, R ₁ to R ₇ 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 aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy ... 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, acyl group, carbonyl group, carboxyl group, ester group, hydroxyl group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof, and wherein said R ₁ to R When ₇ is independently selected from a substituted alkyl group having 1 to 20 carbon atoms, a substituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted heteroalkyl group having 1 to 20 carbon atoms, a substituted aryl group having 6 to 30 carbon atoms, or a substituted heteroaryl group having 3 to 30 carbon atoms, said substituents are hydrogen, deuterium, halogen, an unsubstituted alkyl group having 1 to 20 carbon atoms, an unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, an unsubstituted heteroalkyl group having 1 to 20 carbon atoms, an unsubstituted aralkyl group having 7 to 30 carbon atoms, an unsubstituted aryl group having 1 to 20 carbon atoms, an unsubstituted aryl group having 1 to 20 ring ... unsubstituted alkoxy groups having 6 to 30 carbon atoms, unsubstituted aryloxy groups having 6 to 30 carbon atoms, unsubstituted alkenyl groups having 2 to 20 carbon atoms, unsubstituted aryl groups having 6 to 30 carbon atoms, unsubstituted heteroaryl groups having 3 to 30 carbon atoms, unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, unsubstituted arylsilyl groups having 6 to 20 carbon atoms, unsubstituted amine groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxyl groups, ester groups, hydroxyl groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof.

（Ｒ_１～Ｒ_７は、それぞれ独立して水素、重水素、フッ素、メチル基、エチル基、プロピル基、イソプロピル基、イソブチル基、ｎ－ブチル基、ｔｅｒｔ－ブチル基、ｎ－ペンチル基、イソペンチル基、ネオペンチル基、シクロブチル基、シクロペンチル基、シクロヘキシル基、シアノ基、およびこれらの組合せからなる群から選ばれる。） According to one embodiment of the present invention, L _b is selected from the following structures, which may be the same or different at each occurrence:

(R ₁ to R ₇ are each independently selected from the group consisting of hydrogen, deuterium, fluorine, a methyl group, an ethyl group, a propyl group, an isopropyl group, an isobutyl group, a n-butyl group, a tert-butyl group, a n-pentyl group, an isopentyl group, a neopentyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cyano group, and combinations thereof.)

According to one embodiment of the present invention, each occurrence of L _b is the same or different and is any one selected from the group consisting of L _b1 to L _b322 . For specific structures of L _b1 to L _b322 , please refer to claim 22.

According to an embodiment of the present invention, each occurrence of L _c is the same or different and is any one selected from the group consisting of L _c1 to L _c231 . For specific structures of L _c1 to L _c231 , please refer to claim 23.

According to one embodiment of the present invention, the metal complex has the structure Ir(L _a ) ₂ (L _b ) or Ir(L _a ) ₂ (L _c ) or Ir(L _a )(L _c ) ₂ .

When the metal complex has a structure of Ir(L _a ) ₂ (L _b ), L _a is the same or different at each occurrence and is any one or any two selected from the group consisting of L _a1 to L _a1539 , and L _b is any one selected from the group consisting of L _b1 to L _b322 . When the metal complex has a structure of Ir(L _a ) ₂ (L _c ), L _a is the same or different at each occurrence and is any one or any two selected from the group consisting of L _a1 to L _a1539 , and L _c is any one selected from the group consisting of L _c1 to L _c231 . When the metal complex has a structure of Ir(L _a )(L _c ) ₂ , L _a is any one selected from the group consisting of L _a1 to L _a1539 , and L _c is any one or any two selected from the group consisting of L _c1 to L _c231 , which may be the same or different at each occurrence.

According to one embodiment of the present invention, the metal complex has the structure Ir(L _a ) ₂ (L _b ) or Ir(L _a ) ₂ (L _c ) or Ir(L _a )(L _c ) ₂ .

When the metal complex has a structure of Ir(L _a ) ₂ (L _b ), L _a is the same or different at each occurrence and is any one or any two selected from the group consisting of L _a1 to L _a1611 , and L _b is any one selected from the group consisting of L _b1 to L _b322 . When the metal complex has a structure of Ir(L _a ) ₂ (L _c ), L _a is the same or different at each occurrence and is any one or any two selected from the group consisting of L _a1 to L _a1611 , and L _c is any one selected from the group consisting of L _c1 to L _c231 . When the metal complex has a structure of Ir(L _a )(L _c ) ₂ , L _a is any one selected from the group consisting of L _a1 to L _a1611 , and L _c is any one or any two selected from the group consisting of L _c1 to L _c231 , which may be the same or different at each occurrence.

According to one embodiment of the present invention, the metal complex is selected from the group consisting of Compounds 1 to 300. For specific structures of Compounds 1 to 300, please refer to claim 24.

According to one embodiment of the present invention, the metal complex is selected from the group consisting of Compound 1 to Compound 316. For specific structures of Compound 1 to Compound 316, please refer to claim 24.

（Ｚは、Ｏから選ばれ、
Ｘ_１～Ｘ_８は、出現毎に同一または異なってＣ、ＣＲ_ｘまたはＮから選ばれ、
Ｙ_１～Ｙ_６は、出現毎に同一または異なってＣＲ_ｙまたはＮから選ばれ、
Ｒ_ｘ、Ｒ_ｙは、出現毎に同一または異なって水素、重水素、ハロゲン、置換または非置換の炭素原子数１～２０のアルキル基、置換または非置換の環炭素原子数３～２０のシクロアルキル基、置換または非置換の炭素原子数１～２０のヘテロアルキル基、置換または非置換の炭素原子数７～３０のアラルキル基、置換または非置換の炭素原子数１～２０のアルコキシ基、置換または非置換の炭素原子数６～３０のアリールオキシ基、置換または非置換の炭素原子数２～２０のアルケニル基、置換または非置換の炭素原子数６～３０のアリール基、置換または非置換の炭素原子数３～３０のヘテロアリール基、置換または非置換の炭素原子数３～２０のアルキルシリル基、置換または非置換の炭素原子数６～２０のアリールシリル基、置換または非置換の炭素原子数０～２０のアミン基、アシル基、カルボニル基、カルボキシル基、エステル基、シアノ基、イソシアノ基、ヒドロキシル基、スルファニル基、スルフィニル基、スルホニル基、ホスフィノ基、およびこれらの組合せからなる群から選ばれ、
隣り合う置換基Ｒ_ｘは、結合して環を形成していてもよい。） According to one embodiment of the present invention,
An anode;
A cathode;
Further disclosed is an electroluminescent device comprising an organic layer disposed between the anode and the cathode, the organic layer comprising a metal complex having a photoluminescence spectrum (PL) maximum emission wavelength of 612 nm or more, preferably 615 nm or more, the metal in the metal complex being selected from metals having a relative atomic mass greater than 40 and comprising a ligand L _a having the structure represented by formula 1:

Z is selected from O;
X ₁ to X ₈ are each identically or differently selected from C, CR _x or N;
Y ₁ to Y ₆ are each identically or differently selected from CR _y or N at each occurrence;
R _x and R _y each occur the same or different and each represent 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 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, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxyl group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof;
Adjacent substituents R _x may be bonded to form a ring.

（Ｚは、Ｏ、ＳまたはＳｅから選ばれ、
Ｘ_１～Ｘ_８は、出現毎に同一または異なってＣ、ＣＲ_ｘまたはＮから選ばれ、
Ｙ_１～Ｙ_６は、出現毎に同一または異なってＣＲ_ｙ１、ＣＲ_ｙ２またはＮから選ばれ、且つＹ_１～Ｙ_６の
うちの少なくとも１つは、ＣＲ_ｙ２から選ばれ、前記Ｒ_ｙ２は、－Ｌ－ＳｉＲ_ｓ１Ｒ_ｓ２Ｒ_ｓ３の構造を有し、
Ｒ_ｘ、Ｒ_ｙ１、Ｒ_ｓ１、Ｒ_ｓ２、Ｒ_ｓ３は、出現毎に同一または異なって水素、重水素、ハロゲン、置換または非置換の炭素原子数１～２０のアルキル基、置換または非置換の環炭素原子数３～２０のシクロアルキル基、置換または非置換の炭素原子数１～２０のヘテロアルキル基、置換または非置換の炭素原子数７～３０のアラルキル基、置換または非置換の炭素原子数１～２０のアルコキシ基、置換または非置換の炭素原子数６～３０のアリールオキシ基、置換または非置換の炭素原子数２～２０のアルケニル基、置換または非置換の炭素原子数６～３０のアリール基、置換または非置換の炭素原子数３～３０のヘテロアリール基、置換または非置換の炭素原子数３～２０のアルキルシリル基、置換または非置換の炭素原子数６～２０のアリールシリル基、置換または非置換の炭素原子数０～２０のアミン基、アシル基、カルボニル基、カルボキシル基、エステル基、シアノ基、イソシアノ基、ヒドロキシル基、スルファニル基、スルフィニル基、スルホニル基、ホスフィノ基、およびこれらの組合せからなる群から選ばれ、
Ｌは、単結合、置換または非置換の炭素原子数１～２０のアルキレン基、置換または非置換の炭素原子数３～２０のシクロアルキレン基、置換または非置換の炭素原子数６～２０のアリーレン基、置換または非置換の炭素原子数３～２０のヘテロアリーレン基、またはこれらの組合せからなる群から選ばれ、
隣り合う置換基Ｒ_ｘ、Ｒ_ｓ１、Ｒ_ｓ２、Ｒ_ｓ３は、結合して環を形成していてもよい。） According to one embodiment of the present invention,
An anode;
A cathode;
Further disclosed is an electroluminescent device comprising an organic layer disposed between the anode and the cathode, the organic layer comprising a metal complex, the metal in the metal complex being selected from metals having a relative atomic mass greater than 40 and comprising a ligand L _a having a structure represented by formula 1'.

Z is selected from O, S or Se;
X ₁ to X ₈ are each identically or differently selected from C, CR _x or N;
Y ₁ to Y ₆ are each the same or different and selected from CR _y1 , CR _y2 or N, and at least one of Y ₁ to Y ₆ is selected from CR _y2 , said R _y2 having the structure -L-SiR _s1 R _s2 R _s3 ;
R _x , R _y1 , R _s1 , R _s2 and R _s3 each occur the same or different and each represent 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 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 hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
L is selected from the group consisting of a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;
Adjacent substituents R _x , R _s1 , R _s2 and R _s3 may be bonded to form a ring.

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

According to one embodiment of the invention, the electroluminescent element emits red light.

According to one embodiment of the invention, the electroluminescent element emits white light.

According to one embodiment of the present invention, in the device, the organic layer is an emitting layer, and the emitting layer further contains at least one host material.

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

According to another embodiment of the present invention, a formulation of a compound including a metal complex is further disclosed. The specific structure of the metal complex is shown in any one of the above-mentioned embodiments.

Combination with other materials

The materials of the particular layers used in the organic light-emitting devices described in this invention can be used in combination with various other materials present in the device. These combinations of materials are described in detail in U.S. Patent Application US2016/0359122A1, paragraphs 0132-0161, 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 one of ordinary skill in the art can readily consult the literature to identify other materials that can be used in combination.

It is stated herein that the materials of specific layers used in the organic light emitting device can be used in combination with a variety of other materials present in the device. Illustratively, the light emitting dopants disclosed herein can be used in combination with a variety of hosts, transport layers, blocking layers, injection layers, electrodes and other possible layers. These combinations of materials are described in detail in patent application US2015/0349273A1, paragraphs 0080-0101, 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 readily refer to the literature to identify other materials that can be used in combination.

In the examples of material synthesis, all reactions are carried out under nitrogen protection unless otherwise stated. All reaction solvents are anhydrous and used as obtained from commercial sources. The synthesized products were subjected to structural confirmation and property testing using one or more instruments (including but not limited to Bruker nuclear magnetic resonance, Shimadzu liquid chromatography, liquid chromatography/mass spectrometer, gas chromatography/mass spectrometer, differential scanning calorimeter, Shanghai Liang Optics Fluorescence Spectrophotometer, Wuhan Science & Technology Electrochemical Work Station, Anhui Beike sublimation equipment, etc.) in a manner familiar to those skilled in the art. In the examples of devices, the device properties were also tested using instruments (including but not limited to Angstrom Engineering deposition machine, Suzhou Fusida optical test system, life test system, Beijing Liangtuo ellipsometer, etc.) 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, testing methods, etc., and can reliably and unaffectedly obtain the specific data of the sample, so the above-mentioned relevant content will not be repeated in this specification.

Examples of material synthesis:

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

Synthesis Example 1: Synthesis of Compound 77

Step 1: Synthesis of Intermediate 1

2,6-Dibromo-4-methylphenol (58.2 g, 218.9 mmol) was dissolved in 700 mL of dry DMF. The reaction solution was then cooled to 0°C, and NaH (10.6 g, 281.5 mmol) was added in portions. After addition was complete, the solution was stirred at 0°C until no obvious gas emissions were evident. Then, iodomethane (46.7 g, 328.4 mmol) was added. The reaction was then warmed to room temperature and stirred overnight. After TLC showed the reaction was complete, water and ethyl acetate were added, extracted, and the organic phase was combined. The organic phase was washed multiple times with saturated brine, dried, and spun to completely remove the solvent by rotary evaporation to obtain the crude product. Separation by silica gel column chromatography (eluent is petroleum ether) gave intermediate 1 (57.7 g, 94.3%) as a colorless oily liquid as the target product.

Step 2: Synthesis of intermediate 2

Intermediate 1 (31.7 g, 113.2 mmol) was dissolved in 230 mL of ultra-dry methyl tert-butyl ether (MTBE). The reaction solution was then cooled to -72°C. Next, n-butyllithium solution (50 mL, 125 mmol) was added dropwise under the protection of nitrogen gas. After the addition was completed, the temperature was maintained for 30 min. Then, trimethyl borate (17.6 g, 169.8 mmol) was added. After the addition was completed, the reaction was warmed to room temperature and reacted for 2 h. Then, 250 mL of 2m HCl was added and stirred at room temperature for 2 h. Next, an appropriate amount of methyl tert-butyl ether was added to the reaction, the solution was separated, the aqueous phase was extracted with methyl tert-butyl ether, and the organic phase was combined. It was dried and rotated to completely remove the solvent by rotary evaporation to obtain a crude product that was a yellow solid. Then, 150 mL of n-hexane was added and heated to reflux for 1 h. It was then cooled to room temperature and filtered to collect the solid, which was washed multiple times with hexane and then pumped to dryness to give intermediate 2 (16.5 g, 59.7%) as a white powder.

Step 3: Synthesis of intermediate 3

1-Bromo-2,4-difluoro-3-methylbenzene (14.0 g, 67.6 mmol), intermediate 2 (16.5 g, 67.6 mmol), tetratriphenylphosphine palladium (3.9 g, 3.4 mmol) and sodium carbonate (14.0 g, 132.1 mmol) were placed in a 1 L reaction flask, and 210 mL of toluene, 70 mL of ethanol and 70 mL of water were added. The system was evacuated and replaced with nitrogen gas, and refluxed overnight. After completion of the reaction was detected by TLC, it was cooled to room temperature, diluted with water, extracted with dichloromethane, and the organic phase was combined. It was dried, rotary evaporated, and separated by silica gel column chromatography (eluent was ethyl acetate:petroleum ether=1:100, v/v) to obtain intermediate 3 (12.9 g, 58.3%) as a colorless oily liquid.

Step 4: Synthesis of intermediate 4

Intermediate 3 (12.9 g, 39.4 mmol) was dissolved in 150 mL of dichloromethane. The reaction solution was cooled to 0°C, and boron tribromide (15.3 g, 61.1 mmol) was slowly added. The reaction was continued at this temperature for 2 h. After TLC showed the reaction was complete, the reaction was quenched by carefully adding water, extracted with dichloromethane, and the organic phases were combined. The mixture was dried, rotary evaporated, and separated by silica gel column chromatography (eluent: ethyl acetate: petroleum ether = 1:50, v/v) to obtain intermediate 4 (10.9 g, 88.3%) as a white solid.

Step 5: Synthesis of Intermediate 5

After adding intermediate 4 (13.9 g, 44.4 mmol), potassium carbonate (12.3 g, 89.0 mmol) and DMF (150 mL) to a 250 mL three-neck flask, the resulting reaction mixture was heated to 100 °C under nitrogen gas protection and reacted overnight. After the reaction mixture was cooled to room temperature, water and ethyl acetate were added, extracted, and the organic phase was combined. The organic phase was washed multiple times with saturated saline, dried, and rotated to completely remove the solvent by rotary evaporation to obtain a crude product. Separation by silica gel column chromatography (eluent is petroleum ether) gave intermediate 5 (10.3 g, 79.1%) as a white solid as the target product.

Step 6: Synthesis of Intermediate 6

Intermediate 5 (10.3 g, 35.1 mmol), bis(pinacolato)diboron (11.6 g, 45.7 mmol), Pd(dppf)Cl ₂ (1.3 g, 1.8 mmol), potassium acetate (5.2 g, 53.0 mmol) and 1,4-dioxane (100 mL) were added to a 250 mL three-neck flask, and the resulting reaction mixture was heated to reflux under the protection of nitrogen gas and reacted overnight. After the reaction mixture was cooled to room temperature, water and ethyl acetate were added, extracted, and the organic phase was combined. The organic phase was washed several times with saturated saline, dried, and rotated to completely remove the solvent by rotary evaporation to obtain a crude product. Separation by silica gel column chromatography (eluent was ethyl acetate:petroleum ether=1:50, v/v) gave intermediate 6 (10.2 g, 85.4%) as a white solid as the target product.

Step 7: Synthesis of Intermediate 7

After adding 2,4-dibromoquinoline (6.0 g, 20.9 mmol), intermediate 6 (7.1 g, 20.9 mmol), tetratriphenylphosphine palladium (1.2 g, 1.1 mmol), sodium carbonate (3.3 g, 31.1 mmol), 1,4-dioxane (80 mL) and water (20 mL) to a 250 mL three-neck flask, the resulting reaction mixture was heated to reflux under the protection of nitrogen gas and reacted overnight. The reaction mixture was cooled to room temperature and then filtered. The resulting solid was washed multiple times with water and petroleum ether in turn and then dried to obtain a crude product. Separation by silica gel column chromatography (eluent: dichloromethane: petroleum ether = 1:3, v/v) gave intermediate 7 (5.7 g, 65.2%) as a white solid as the target product.

Step 8: Synthesis of Intermediate 8

After dissolving intermediate 7 (5.2 g, 12.4 mmol) in 250 mL of ultra-dry tetrahydrofuran, the reaction solution was cooled to -72°C. Next, n-butyllithium solution (5.5 mL, 13.6 mmol) was added dropwise under the protection of nitrogen gas. After the addition was completed, the temperature was maintained for 1 h. Then, trimethylsilyl trifluoromethanesulfonate (TMSOTf) (3.3 g, 14.9 mmol) was added. After the addition was completed, the reaction was warmed to room temperature and reacted for 2 h. Then, the reaction was quenched by adding saturated sodium bicarbonate solution. Next, ethyl acetate was added to the reaction and the solution was separated. The aqueous phase was extracted with ethyl acetate and the organic phase was combined. It was dried and rotated to completely remove the solvent by rotary evaporation to obtain a crude product. Separation by silica gel column chromatography (eluent: dichloromethane: petroleum ether = 1:3, v/v) gave the target product, intermediate 8 (3.2 g, 62.4%), which was a white solid.

Step 9: Synthesis of the Iridium Dimer

A mixture of intermediate 8 (2.6 g, 6.3 mmol), iridium trichloride trihydrate (554 mg, 1.6 mmol), 2-ethoxyethanol (21 mL) and water (7 mL) was refluxed continuously for 24 hours under the protection of nitrogen gas. After cooling to room temperature, the water in the solution was carefully removed by rotary evaporation to obtain an ethoxyethanol solution of iridium dimer. No further purification is required and it can be used directly in the next reaction.

Step 10: Synthesis of Compound 77

The ethoxyethanol solution of iridium dimer obtained in step 9, 3,7-diethyl-1,1,1-trifluoromethylnonane-4,6-dione (511 mg, 2.4 mmol) and potassium carbonate (1.1 g, 8 mmol) were added to a 100 mL round-bottom flask and reacted at room temperature for 24 hours under the protection of nitrogen gas. It was then poured into a diatomaceous earth funnel, filtered and washed with ethanol. Dichloromethane was added to the obtained solid and the filtrate was collected. Then, ethanol was added to concentrate the obtained solution but not completely. After filtration, 0.52 g of product compound 77 (yield 25.3%) was obtained. The product was further purified by column chromatography. The structure of the compound was confirmed by NMR and LC-MS as the target product with a molecular weight of 1282.4.

Synthesis Example 2: Synthesis of Compound 73

Step 1: Synthesis of intermediate 9

Intermediate 1 (57.7 g, 206 mmol), 2-fluorophenylboronic acid (28.8 g, 206 mmol), tetratriphenylphosphine palladium (4.76 g, 4.1 mmol) and sodium carbonate (42.7 g, 309 mmol) were placed in a 1 L reaction flask, and 300 mL of toluene, 100 mL of ethanol and 100 mL of water were added. The system was evacuated and replaced with nitrogen gas, and refluxed overnight. After completion of the reaction was detected by TLC, it was cooled to room temperature, diluted with water, extracted with dichloromethane, and the organic phase was combined. It was dried, rotary evaporated, and separated by silica gel column chromatography (eluent was ethyl acetate:petroleum ether=1:100, v/v) to obtain intermediate 9 (39 g, 64.1%) as a colorless oily liquid.

Step 2: Synthesis of intermediate 10

Intermediate 9 (39 g, 132.1 mmol) was dissolved in 500 mL of dichloromethane. After the reaction solution was cooled to 0°C, boron tribromide (49.7 g, 198.2 mmol) was slowly added, and the reaction was continued at this temperature for 2 h. After TLC showed the reaction was complete, the reaction was quenched by carefully adding water, extracted with dichloromethane, and the organic phases were combined. The mixture was dried, rotary evaporated, and separated by silica gel column chromatography (eluent: ethyl acetate:petroleum ether = 1:50, v/v) to obtain intermediate 10 (31.8 g, 85.5%) as a white solid.

Step 3: Synthesis of intermediate 11

Intermediate 10 (31.8 g, 113 mmol), potassium carbonate (31.3 g, 226 mmol), and DMF (300 mL) were added to a 500 mL three-neck flask. The resulting reaction mixture was then heated at 100° C. under nitrogen gas protection and reacted overnight. After the reaction mixture was cooled to room temperature, water and ethyl acetate were added, extracted, and the organic phase was combined. The organic phase was washed multiple times with saturated saline, dried, and rotated to completely remove the solvent by rotary evaporation to obtain a crude product. Separation by silica gel column chromatography (eluent is petroleum ether) gave intermediate 11 (16.4 g, 55.6%) as a white solid as the target product.

Step 4: Synthesis of intermediate 12

In a 250 mL three-neck flask, intermediate 11 (16.4 g, 62.8 mmol), bis(pinacolato)diboron (20.7 g, 81.6 mmol), Pd(dppf)Cl ₂ (1.4 g, 1.9 mmol), potassium acetate (9.2 g, 94.2 mmol) and 1,4-dioxane (300 mL) were added, and the resulting reaction mixture was heated to reflux under the protection of nitrogen gas and reacted overnight. After the reaction mixture was cooled to room temperature, water and ethyl acetate were added, extracted, and the organic phase was combined. The organic phase was washed several times with saturated brine, dried, and rotated to completely remove the solvent by rotary evaporation to obtain a crude product. Separation by silica gel column chromatography (eluent was ethyl acetate:petroleum ether=1:50, v/v) gave intermediate 12 (13.5 g, 69.8%) as a white solid as the target product.

Step 5: Synthesis of intermediate 13

After adding 2,4-dibromoquinoline (6.15 g, 21.4 mmol), intermediate 12 (6.6 g, 21.4 mmol), tetratriphenylphosphine palladium (1.2 g, 1.1 mmol), sodium carbonate (3.4 g, 32.1 mmol), 1,4-dioxane (90 mL) and water (20 mL) to a 250 mL three-neck flask, the resulting reaction mixture was heated to reflux under the protection of nitrogen gas and reacted overnight. The reaction mixture was cooled to room temperature and then filtered. The resulting solid was washed multiple times with water and petroleum ether, and then dried to obtain a crude product. Separation by silica gel column chromatography (eluent: dichloromethane: petroleum ether = 1:3, v/v) gave intermediate 13 (5.2 g, 62.6%) as a white solid as the target product.

Step 6: Synthesis of intermediate 14

Intermediate 13 (5.2 g, 13.4 mmol) was dissolved in 134 mL of ultra-dry tetrahydrofuran and the reaction solution was cooled to -72°C. Next, n-butyllithium solution (6.4 mL, 12.0 mmol) was added dropwise under the protection of nitrogen gas. After the addition was completed, the temperature was maintained for 30 min. Then, trimethylsilyl trifluoromethanesulfonate (TMSOTf) (4.2 g, 18.8 mmol) was added. After the addition was completed, the reaction was warmed to room temperature and reacted for 2 h. Then, the reaction was quenched by adding saturated sodium bicarbonate solution. Next, ethyl acetate was added to the reaction and the solution was separated. The aqueous phase was extracted with ethyl acetate and the organic phase was combined. It was dried and rotated to completely remove the solvent by rotary evaporation to obtain a crude product. Separation by silica gel column chromatography (eluent: dichloromethane: petroleum ether = 1:2, v/v) gave the target product, intermediate 14 (3.2 g, 62.7%), which was a white solid.

Step 7: Synthesis of Iridium Dimer:

A mixture of intermediate 14 (3 g, 7.9 mmol), iridium trichloride trihydrate (693 mg, 2.0 mmol), 2-ethoxyethanol (21 mL) and water (7 mL) was refluxed continuously for 24 hours under the protection of nitrogen gas. After cooling to room temperature, the water in the solution was carefully removed by rotary evaporation to obtain an ethoxyethanol solution of iridium dimer. No further purification is required and it can be used directly in the next reaction.

Step 8: Synthesis of Compound 73

The ethoxyethanol solution of iridium dimer obtained in step 7, 3,7-diethyl-1,1,1-trifluoromethylnonane-4,6-dione (798 mg, 3.0 mmol) and potassium carbonate (1.38 g, 10.0 mmol) were added to a 100 mL round bottom flask and reacted at room temperature for 24 hours under the protection of nitrogen gas. It was then poured into a diatomaceous earth funnel, filtered and washed with ethanol. Dichloromethane was added to the obtained solid and the filtrate was collected. Then, ethanol was added to concentrate the obtained solution but not completely. After filtration, 1.2 g of product compound 73 (yield 49.2%) was obtained. The product was further purified by column chromatography. The structure of the compound was confirmed by NMR and LC-MS as the target product with a molecular weight of 1218.4.

Synthesis Example 3: Synthesis of Compound 128

Step 1: Synthesis of intermediate 15

Intermediate 1 (35 g, 125 mmol), 2,4-difluorophenylboronic acid (19.7 g, 125 mmol), tetratriphenylphosphine palladium (2.89 g, 2.5 mmol) and potassium carbonate (34.6 g, 250 mmol) were placed in a 1 L reaction flask, and 375 mL of 1,4-dioxane and 125 mL of water were added. The system was evacuated and replaced with nitrogen gas, and refluxed overnight. After completion of the reaction was detected by TLC, it was cooled to room temperature, diluted with water, extracted with dichloromethane, and the organic phases were combined. It was dried, rotary evaporated, and separated by silica gel column chromatography (eluent was ethyl acetate:petroleum ether=1:100, v/v) to obtain intermediate 15 (15.6 g, 39.8%) as a colorless oily liquid.

Step 2: Synthesis of intermediate 16

Intermediate 15 (15.6 g, 49.8 mmol) was dissolved in 200 mL of dichloromethane. The reaction solution was cooled to 0°C, and boron tribromide (18.7 g, 74.7 mmol) was slowly added. The reaction was continued at this temperature for 2 h. After TLC showed the reaction was complete, the reaction was quenched by carefully adding water, extracted with dichloromethane, and the organic phases were combined. The mixture was dried, rotary evaporated, and separated by silica gel column chromatography (eluent: ethyl acetate: petroleum ether = 1:50, v/v) to obtain intermediate 16 (12.1 g, 81.2%) as a white solid.

Step 3: Synthesis of intermediate 17

In a 500 mL three-neck flask, intermediate 16 (12.1 g, 40.5 mmol), potassium carbonate (11.2 g, 80.9 mmol), and DMF (150 mL) were added in that order. The resulting reaction mixture was then heated at 100° C. under the protection of nitrogen gas and reacted overnight. After the reaction mixture was cooled to room temperature, water and ethyl acetate were added, extracted, and the organic phase was combined. The organic phase was washed multiple times with saturated saline, dried, and rotated to completely remove the solvent by rotary evaporation to obtain a crude product. Separation by silica gel column chromatography (eluent is petroleum ether) gave intermediate 17 (9.8 g, 86.7%) as a white solid as the target product.

Step 4: Synthesis of intermediate 18

In a 500 mL three-neck flask, intermediate 17 (9.8 g, 35.1 mmol), bis(pinacolato)diboron (11.6 g, 45.6 mmol), Pd(dppf)Cl ₂ (1.3 g, 1.8 mmol), potassium acetate (5.2 g, 52.7 mmol) and 1,4-dioxane (300 mL) were added in order. The resulting reaction mixture was heated to reflux under the protection of nitrogen gas and reacted overnight. After the reaction was completed, the reaction mixture was cooled to room temperature, water and ethyl acetate were added, extracted, the solution was separated and the organic phase was combined. The organic phase was washed with saturated brine several times, dried and rotated to completely remove the solvent by rotary evaporation to obtain a crude product. Separation by silica gel column chromatography (eluent was ethyl acetate:petroleum ether=1:50, v/v) gave intermediate 18 (9.5 g, 83.0%) as a white solid as the target product.

Step 5: Synthesis of intermediate 19

2-Chloro-6-bromoquinoline (5 g, 20.6 mmol) was dissolved in 40 mL of ultra-dry tetrahydrofuran, and the reaction solution was cooled to -72°C. Next, under the protection of nitrogen gas, n-butyllithium solution (9 mL, 22.7 mmol) was added dropwise. After the addition was completed, the temperature was maintained for 30 min. Then, trimethylchlorosilane (TMSCl) (2.7 g, 24.7 mmol) was added, and after the addition was completed, the reaction was warmed to room temperature and reacted for 2 h. Then, the reaction was quenched by adding saturated sodium bicarbonate solution. Next, ethyl acetate was added to the reaction system, the solution was separated, the aqueous phase was extracted with ethyl acetate, and the organic phase was combined. It was dried and rotated to completely remove the solvent by rotary evaporation to obtain a crude product. Separation by silica gel column chromatography (eluent: ethyl acetate: petroleum ether = 1:100, v/v) gave the target product, intermediate 19 (4.2 g, 86.5%), which was a white solid.

Step 6: Synthesis of intermediate 20

Intermediate 19 (870 mg, 3.7 mmol), intermediate 18 (1.27 g, 3.89 mmol), tetratriphenylphosphine palladium (214 mg, 0.2 mmol), sodium carbonate (588 mg, 5.6 mmol), 1,4-dioxane (16 mL) and water (4 mL) were added to a 250 mL three-neck flask, and the resulting reaction mixture was heated to reflux under nitrogen gas protection and reacted overnight. The reaction mixture was cooled to room temperature and then filtered. The resulting solid was washed multiple times with water and petroleum ether, and then dried to obtain a crude product. Separation by silica gel column chromatography (eluent: ethyl acetate: petroleum ether = 1:100, v/v) gave intermediate 20 (1.28 g, 86.8%) as a white solid as the target product.

Step 7: Synthesis of Iridium Dimer:

A mixture of intermediate 20 (1.28 g, 3.2 mmol), iridium trichloride trihydrate (283 mg, 0.8 mmol), 2-ethoxyethanol (9 mL) and water (3 mL) was refluxed continuously for 24 hours under the protection of nitrogen gas. After cooling to room temperature, the water in the solution was carefully removed by rotary evaporation to obtain an ethoxyethanol solution of iridium dimer. No further purification is required and it can be used directly in the next reaction.

Step 8: Synthesis of Compound 128

The ethoxyethanol solution of iridium dimer obtained in step 7, 3,7-diethyl-3-methylnonane-4,6-dione sodium salt (298 mg, 1.2 mmol) and potassium carbonate (553 mg, 4 mmol) were added to a 50 mL round-bottom flask and reacted at 60° C. for 24 hours under the protection of nitrogen gas. It was then poured into a diatomaceous earth funnel, filtered and washed with ethanol. Dichloromethane was added to the obtained solid and the filtrate was collected. Then, ethanol was added to concentrate the obtained solution but not completely. After filtration, 400 mg of product compound 128 (yield 41.1%) was obtained. The product was further purified by column chromatography. The structure of the compound was confirmed by NMR and LC-MS as the target product with a molecular weight of 1214.4.

Synthesis Example 4: Synthesis of Compound 164

Step 1: Synthesis of iridium dimer:

A mixture of intermediate 20 (2.9 g, 7.2 mmol), iridium trichloride trihydrate (640 mg, 1.8 mmol), 2-ethoxyethanol (21 mL) and water (7 mL) was refluxed continuously for 24 hours under the protection of nitrogen gas. After cooling to room temperature, the water in the solution was carefully removed by rotary evaporation to obtain an ethoxyethanol solution of iridium dimer. No further purification is required and it can be used directly in the next reaction.

Step 2: Synthesis of Compound 164

The ethoxyethanol solution of iridium dimer obtained in step 1, 3,7-diethyl-3,7-dimethylnonane-4,6-dione (650 mg, 2.7 mmol) and potassium carbonate (1.2 g, 9.1 mmol) were added to a 10 mL round-bottom flask and reacted at 60°C for 24 hours under the protection of nitrogen gas. It was then poured into a diatomaceous earth funnel, filtered and washed with ethanol. Dichloromethane was added to the obtained solid and the filtrate was collected. Then, ethanol was added to concentrate the obtained solution but not completely. After filtration, 780 mg of product compound 164 (yield 63.5%) was obtained. The product was further purified by column chromatography. The structure of the compound was confirmed by NMR and LC-MS as the target product with a molecular weight of 1228.4.

Synthesis Example 5: Synthesis of Compound 74

Step 1: Synthesis of intermediate 21

2,4-dibromo-6-chloroquinoline (5.95 g, 18.5 mmol), intermediate 12 (5.7 g, 21.4 mmol), tetratriphenylphosphine palladium (1.1 g, 0.93 mmol), sodium carbonate (2.94 g, 27.8 mmol), 1,4-dioxane (80 mL) and water (20 mL) were added to a 250 mL three-neck flask, and the resulting reaction mixture was heated to reflux under nitrogen gas protection and reacted overnight. The reaction mixture was cooled to room temperature and then filtered. The resulting solid was washed multiple times with water and petroleum ether, and then dried to obtain a crude product. Separation by silica gel column chromatography (eluent: dichloromethane: petroleum ether = 1:4, v/v) gave intermediate 21 (4.5 g, 57.3%) as a white solid as the target product.

Step 2: Synthesis of intermediate 22

Intermediate 21 (4.5 g, 10.6 mmol) was dissolved in 100 mL of ultra-dry tetrahydrofuran and the reaction solution was cooled to -72°C. Next, under the protection of nitrogen gas, n-butyllithium solution (5.1 mL, 12.8 mmol) was added dropwise. After the addition was completed, the temperature was maintained for 30 min. Then, trimethylsilyl trifluoromethanesulfonate (TMSOTf) (3.3 g, 14.8 mmol) was added. After the addition was completed, the reaction was warmed to room temperature and reacted for 2 h. Then, the reaction was quenched by adding saturated sodium bicarbonate solution. Next, ethyl acetate was added to the reaction and the solution was separated. The aqueous phase was extracted with ethyl acetate and the organic phase was combined. It was dried and rotated to completely remove the solvent by rotary evaporation to obtain a crude product. Separation by silica gel column chromatography (eluent: dichloromethane: petroleum ether = 1:3, v/v) gave the target product, intermediate 22 (3.37 g, 76.4%), which was a white solid.

Step 3: Synthesis of intermediate 23

Intermediate 22 (3.37 g, 8.1 mmol), isobutyl borate (1.65 g, 16.2 mmol), palladium acetate (91 mg, 0.4 mmol), Sphos (333 mg, 0.8 mmol), potassium phosphate trihydrate (6.47 g, 24.3 mmol) and toluene (60 mL) were added to a 250 mL three-neck flask, and the resulting reaction mixture was heated to reflux under nitrogen gas protection and reacted overnight. After the reaction mixture was cooled to room temperature, it was poured into a diatomaceous earth-filled funnel, filtered, and the filtrate was collected and rotated to completely remove the solvent by rotary evaporation to obtain a crude product. Separation by silica gel column chromatography (eluent: dichloromethane: petroleum ether = 1:3, v/v) gave intermediate 23 (3.1 g, 87.4%) as a white solid as the target product.

Step 4: Synthesis of Iridium Dimer:

A mixture of intermediate 23 (2 g, 4.56 mmol), iridium trichloride trihydrate (404 mg, 1.16 mmol), 2-ethoxyethanol (36 mL) and water (12 mL) was refluxed continuously for 24 hours under the protection of nitrogen gas. After cooling to room temperature, the water in the solution was carefully removed by rotary evaporation to obtain an ethoxyethanol solution of iridium dimer. No further purification is required and it can be used directly in the next reaction.

Step 5: Synthesis of Compound 74

The ethoxyethanol solution of iridium dimer obtained in step 4, 3,7-diethyl-1,1,1-trifluorononane-4,6-dione (464 mg, 1.76 mmol) and potassium carbonate (0.8 g, 5.8 mmol) were added to a 100 mL round-bottom flask and reacted at room temperature for 24 hours under the protection of nitrogen gas. It was then poured into a diatomaceous earth funnel, filtered and washed with ethanol. Dichloromethane was added to the obtained solid and the filtrate was collected. Then, ethanol was added to concentrate the obtained solution but not completely. After filtration, 0.85 g of product compound 74 (yield 55.1%) was obtained. The product was further purified by column chromatography. The structure of the compound was confirmed by NMR and LC-MS as the target product with a molecular weight of 1330.5.

Synthesis Example 6: Synthesis of Compound 122

Step 1: Synthesis of intermediate 24

2,4-dibromo-7-chloroquinoline (6 g, 18.7 mmol), intermediate 12 (5.75 g, 18.7 mmol), tetratriphenylphosphine palladium (1.1 g, 0.93 mmol), sodium carbonate (2.97 g, 28.1 mmol), 1,4-dioxane (80 mL) and water (20 mL) were added to a 250 mL three-neck flask, and the resulting reaction mixture was heated to reflux under nitrogen gas protection and reacted overnight. The reaction mixture was cooled to room temperature and then filtered. The resulting solid was washed multiple times with water and petroleum ether, and then dried to obtain a crude product. Separation by silica gel column chromatography (eluent: dichloromethane: petroleum ether = 1:5, v/v) gave intermediate 24 (3.6 g, 45.6%) as a white solid as the target product.

Step 2: Synthesis of intermediate 25

Intermediate 24 (3.6 g, 8.52 mmol) was dissolved in 85 mL of ultra-dry tetrahydrofuran and the reaction solution was cooled to -72°C. Next, under the protection of nitrogen gas, n-butyllithium solution (4.1 mL, 10.2 mmol) was added dropwise. After the addition was completed, the temperature was maintained for 30 min. Then, trimethylsilyl trifluoromethanesulfonate (TMSOTf) (2.64 g, 11.9 mmol) was added. After the addition was completed, the reaction was warmed to room temperature and reacted for 2 h. Then, the reaction was quenched by adding saturated sodium bicarbonate solution. Next, ethyl acetate was added to the reaction and the solution was separated. The aqueous phase was extracted with ethyl acetate and the organic phase was combined. It was dried and rotated to completely remove the solvent by rotary evaporation to obtain a crude product. Separation by silica gel column chromatography (eluent: dichloromethane: petroleum ether = 1:4, v/v) gave the target product, intermediate 25 (1.8 g, 50.8%), which was a white solid.

Step 3: Synthesis of intermediate 26

Intermediate 25 (1.8 g, 4.3 mmol), isobutyl borate (0.88 g, 8.65 mmol), palladium acetate (49 mg, 0.22 mmol), Sphos (181 mg, 0.43 mmol), potassium phosphate trihydrate (3.46 g, 13.0 mmol) and toluene (30 mL) were added to a 100 mL three-neck flask, and the resulting reaction mixture was heated to reflux under nitrogen gas protection and reacted overnight. After the reaction mixture was cooled to room temperature, it was poured into a diatomaceous earth-filled funnel, filtered, and the filtrate was collected and rotated to completely remove the solvent by rotary evaporation to obtain a crude product. Separation by silica gel column chromatography (eluent: dichloromethane: petroleum ether = 1:3, v/v) gave intermediate 26 (1.74 g, 91.8%) as a white solid as the target product.

Step 4: Synthesis of Iridium Dimer:

A mixture of intermediate 26 (0.3 g, 0.69 mmol), iridium trichloride trihydrate (60 mg, 0.17 mmol), 2-ethoxyethanol (6 mL) and water (2 mL) was refluxed continuously for 24 hours under the protection of nitrogen gas. After cooling to room temperature, the water in the solution was carefully removed by rotary evaporation to obtain an ethoxyethanol solution of iridium dimer. No further purification is required and it can be used directly in the next reaction.

Step 5: Synthesis of Compound 122

The ethoxyethanol solution of iridium dimer obtained in step 4, 3,7-diethyl-3-methylnonane-4,6-dione (77 mg, 0.34 mmol) and potassium carbonate (117 mg, 0.85 mmol) were added to a 50 mL round-bottom flask and reacted at room temperature for 24 hours under the protection of nitrogen gas. It was then poured into a diatomaceous earth funnel, filtered and washed with ethanol. Dichloromethane was added to the obtained solid and the filtrate was collected. Then, ethanol was added to concentrate the obtained solution but not completely. After filtration, 80 mg of product compound 122 (yield 36.5%) was obtained. The product was further purified by column chromatography. The structure of the compound was confirmed by NMR and LC-MS as the target product with a molecular weight of 1290.6.

Synthesis Example 7: Synthesis of Compound 110

Step 1: Synthesis of iridium dimer:

A mixture of intermediate 23 (0.5 g, 1.14 mmol), iridium trichloride trihydrate (101 mg, 0.29 mmol), 2-ethoxyethanol (9 mL) and water (3 mL) was refluxed continuously for 24 hours under the protection of nitrogen gas. After cooling to room temperature, the water in the solution was carefully removed by rotary evaporation to obtain an ethoxyethanol solution of iridium dimer. No further purification is required and it can be used directly in the next reaction.

Step 2: Synthesis of Compound 110

The ethoxyethanol solution of iridium dimer obtained in step 1, 3,7-diethyl-3-methylnonane-4,6-dione (108 mg, 0.44 mmol) and potassium carbonate (200 mg, 1.45 mmol) were added to a 100 mL round-bottom flask. The mixture was reacted at room temperature for 24 hours under the protection of nitrogen gas. It was then poured into a diatomaceous earth funnel, filtered and washed with ethanol. Dichloromethane was added to the obtained solid and the filtrate was collected. Then, ethanol was added to concentrate the obtained solution, but not completely. After filtration, 0.15 g of product compound 110 (yield 40.1%) was obtained. The product was further purified by column chromatography. The structure of the compound was confirmed by NMR and LC-MS as the target product with a molecular weight of 1290.6.

Synthesis Example 8: Synthesis of compound 307

Step 1: Synthesis of iridium dimer:

A mixture of intermediate 27 (1.8 g, 4.11 mmol), iridium trichloride trihydrate (363 mg, 1.03 mmol), 2-ethoxyethanol (22.5 mL) and water (7.5 mL) was refluxed continuously for 24 hours under the protection of nitrogen gas. After cooling to room temperature, the water in the solution was carefully removed by rotary evaporation to obtain an ethoxyethanol solution of iridium dimer. No further purification is required and it can be used directly in the next reaction.

Step 2: Synthesis of compound 307

The ethoxyethanol solution of iridium dimer obtained in step 1, 3,7-diethyl-3,5-dimethylnonane-4,6-dione (208 mg, 0.87 mmol) and sodium hydroxide (46 mg, 1.16 mmol) were added to a 100 mL round-bottom flask and reacted at room temperature for 24 hours under the protection of nitrogen gas. Then, it was poured into a diatomaceous earth funnel, filtered and washed with ethanol. Dichloromethane was added to the obtained solid and the filtrate was collected. Then, ethanol was added to concentrate the obtained solution but not completely. After filtration, 0.44 g of product compound 307 (yield 65.4%) was obtained. The product was further purified by column chromatography. The structure of the compound was confirmed by NMR and LC-MS as the target product with a molecular weight of 1304.6.

Synthesis Example 9: Synthesis of Compound 311

Step 1: Synthesis of iridium dimer

A mixture of intermediate 28 (4.5 g, 11.7 mmol), iridium trichloride trihydrate (1.03 g, 2.93 mmol), 2-ethoxyethanol (60 mL) and water (20 mL) was refluxed continuously for 24 hours under the protection of nitrogen gas. After cooling to room temperature, the water in the solution was carefully removed by rotary evaporation to obtain an ethoxyethanol solution of iridium dimer. No further purification is required and it can be used directly in the next reaction.

Step 2: Synthesis of compound 311

The ethoxyethanol solution of iridium dimer obtained in step 1, 3,7-diethyl-3,5-dimethylnonane-4,6-dione (703 mg, 2.93 mmol) and sodium hydroxide (234 mg, 5.86 mmol) were added to a 250 mL round-bottom flask and reacted at room temperature for 24 hours under the protection of nitrogen gas. Then, it was poured into a diatomaceous earth funnel, filtered and washed with ethanol. Dichloromethane was added to the obtained solid and the filtrate was collected. Then, ethanol was added to concentrate the obtained solution but not completely. After filtration, 1.1 g of product compound 311 (yield 62.8%) was obtained. The product was further purified by column chromatography. The structure of the compound was confirmed by NMR and LC-MS as the target product with a molecular weight of 1196.5.

Synthesis Example 10: Synthesis of Compound 304

Step 1: Synthesis of iridium dimer:

A mixture of intermediate 29 (2.4 g, 5.52 mmol), iridium trichloride trihydrate (480 mg, 1.36 mmol), 2-ethoxyethanol (30 mL) and water (10 mL) was refluxed continuously for 24 hours under the protection of nitrogen gas. After cooling to room temperature, the water in the solution was carefully removed by rotary evaporation to obtain an ethoxyethanol solution of iridium dimer. No further purification is required and it can be used directly in the next reaction.

Step 2: Synthesis of Compound 304

The ethoxyethanol solution of iridium dimer obtained in step 1, 3,7-diethyl-3-methylnonane-4,6-dione (462 mg, 2.04 mmol) and potassium carbonate (936 mg, 6.8 mmol) were added to a 100 mL round-bottom flask and reacted at room temperature for 24 hours under the protection of nitrogen gas. It was then poured into a diatomaceous earth funnel, filtered and washed with ethanol. Dichloromethane was added to the obtained solid and the filtrate was collected. Then, ethanol was added to concentrate the obtained solution but not completely. After filtration, 640 mg of product compound 304 (yield 72.6%) was obtained. The product was further purified by column chromatography. The structure of the compound was confirmed by NMR and LC-MS as the target product with a molecular weight of 1296.6.

Synthesis Example 11: Synthesis of Compound 313

Step 1: Synthesis of iridium dimer:

A mixture of intermediate 30 (1 g, 2.19 mmol), iridium trichloride trihydrate (193 mg, 0.55 mmol), 2-ethoxyethanol (9 mL) and water (3 mL) was refluxed continuously for 24 hours under the protection of nitrogen gas. After cooling to room temperature, the water in the solution was carefully removed by rotary evaporation to obtain an ethoxyethanol solution of iridium dimer. No further purification is required and it can be used directly in the next reaction.

Step 2: Synthesis of compound 313

The ethoxyethanol solution of iridium dimer obtained in step 1, 3,7-diethyl-3-methylnonane-4,6-dione (373 mg, 1.65 mmol) and potassium carbonate (380 mg, 2.75 mmol) were added to a 100 mL round-bottom flask and reacted at room temperature for 24 hours under the protection of nitrogen gas. Then, it was poured into a diatomaceous earth funnel, filtered and washed with ethanol. Dichloromethane was added to the obtained solid and the filtrate was collected. Then, ethanol was added to concentrate the obtained solution but not completely. After filtration, 0.21 g of product compound 313 (yield 57.5%) was obtained. The product was further purified by column chromatography. The structure of the compound was confirmed by NMR and LC-MS as the target product with a molecular weight of 1326.5.

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

Spectral data

Photoluminescence spectrum (PL) data of the compounds of the present invention and the comparative compounds was measured using a fluorescence spectrophotometer with model number Liang Optics F98 manufactured by Shanghai Liang Optics Technology Co., Ltd. Samples in the examples and comparative examples were each prepared into a solution with a concentration of 3×10 ⁻⁵ mol/L in HPLC-grade dichloromethane, and then excited with light of a wavelength of 500 nm at room temperature (298 K) to measure the emission spectrum. The measurement results are shown in Table 1.

Device Example 1
First, a glass substrate having an indium tin oxide (ITO) anode with a thickness of 120 nm was cleaned and then treated with oxygen plasma and UV ozone. After the treatment, the substrate was dried in a glove box to remove water. Then, the substrate was mounted on a substrate holder and placed in a vacuum chamber. Hereinafter, for the designated organic layers, deposition was performed on the ITO anode in sequence by hot vacuum deposition at a rate of 0.2 to 2 angstroms/second when the vacuum degree was about 10 ^-8 Torr. Compound HI was used as a hole injection layer (HIL). Compound HT was used as a hole transport layer (HTL). Compound EB was used as an electron blocking layer (EBL). Then, Compound 77 in the present invention was doped into the host compound RH and used as an emitting layer (EML). Compound HB was used as a hole blocking layer (HBL). On the HBL, the compound ET and 8-hydroxyquinoline-lithium (Liq) were co-evaporated as an electron transport layer (ETL). Finally, 1 nm of Liq was evaporated as an electron injection layer, and 120 nm of Al was evaporated as a cathode. The device was then transferred to a glove box and encapsulated with a glass cover and a moisture absorbent to complete the device.

Element Example 2
The preparation method of device example 2 is similar to device example 1, except that compound 128 of the present invention is substituted for compound 77 of the present invention in the light-emitting layer (EML).

Device Example 3
The preparation method of device example 3 is similar to device example 1, except that compound 164 of the present invention is substituted for compound 77 of the present invention in the light-emitting layer (EML).

Element Example 4
The preparation method of device example 4 is similar to device example 1, except that compound 73 of the present invention is substituted for compound 77 of the present invention in the light-emitting layer (EML).

Device Example 5
The preparation method of device example 5 is the same as device example 1, except that compound 74 of the present invention is substituted for compound 77 of the present invention in the light-emitting layer (EML).

Device Example 6
The preparation method of device Example 6 is the same as that of device Example 1, except that in the light-emitting layer (EML), compound 122 of the present invention is substituted for compound 77 of the present invention, and the weight ratio of compound 122 to compound RH is 2.5:97.5.

Device Example 7
The preparation method of device example 7 is the same as device example 1, except that compound 307 of the present invention is substituted for compound 77 of the present invention in the light-emitting layer (EML).

Device Example 8
The preparation method of device example 8 is the same as device example 6, except that compound 304 of the present invention is substituted for compound 122 of the present invention in the light-emitting layer (EML).

Device Example 9
The preparation method of device example 9 is the same as device example 1, except that compound 311 of the present invention is substituted for compound 77 of the present invention in the light-emitting layer (EML).

Comparative Example 1 of the Element
The preparation method of Comparative Example 1 of the device is the same as that of Example 1 of the device, except that the comparative compound is substituted for Compound 77 of the present invention in the light-emitting layer (EML).

The layer structure and thickness of the element are shown in the table below. Layers using more than one material are obtained by doping with different compounds in the weight ratios mentioned above.

The structure of the material used in the element is represented as follows:

The IVL characteristics of the device were measured. The CIE, maximum emission wavelength (λ _max ), voltage, full width at half maximum (FWHM) and external quantum efficiency (EQE) data measured at a current density of 15 mA/cm ² are shown in Table 3.

Summary As can be seen from Table 1, in the structure of the ligand L _a according to the present invention, the introduction of silyl substituents effectively shifts the emission wavelength of the material from the light red region to the deep red region obviously red-shifted. At the same time, the CIE and λ _max in Table 3 also further prove this. In addition, by observing the voltage, FWHM and EQE data in Table 3, it is found that the introduction of silyl substituents obviously improves the external quantum efficiency while maintaining a similar low voltage and narrow full width at half maximum, indicating that the silyl substituents have the effect of changing the emission wavelength and improving the emission efficiency in the compound according to the present invention.

Among the above comparisons, Example 4 and Comparative Example 1 are the most direct comparisons. The luminescent material in Example 4 is compound 73, and the luminescent material in Comparative Example 1 is the comparative compound, with the PL λ _max of compound 73 being 622 nm and the PL λ _max of the comparative compound being 609 nm. In the device, their CIEx are 0.678 and 0.655, respectively, and the efficiencies are 21.25% and 20.33%, respectively. The data certainly proves the superiority of the silyl substituent. In addition, the luminescent materials used in Examples 1 to 8 are those in which the silyl substituent is introduced at different positions. For example, Examples 2, 3 and 7 are those in which the silyl group is substituted on the benzene ring in the quinoline ring, and Examples 1, 4, 5, 6 and 8 are those in which the silyl group is substituted on the pyridine ring in the quinoline ring. The CIEx in Examples 2, 3 and 7 are 0.668, 0.670 and 0.667, respectively, and the CIEx in Examples 1, 4, 5, 6 and 8 are 0.684, 0.678, 0.671, 0.679 and 0.679, respectively, which proves that the red shift generated when the silyl group is substituted on the benzene ring of the quinoline ring is slightly less than the red shift generated when the silyl group is substituted on the pyridine ring of the quinoline ring, and proves that the excellent effect of fine-tuning the device CIE while realizing deep red emission can be achieved by adjusting the substitution position of the silyl group on the quinoline ring.In addition, the EQE in Example 7 reaches 25.19%, which proves that high device efficiency can be provided when the silyl group is substituted on the benzene ring of the quinoline ring.

Compound 311 as the luminescent material in Example 9 has fluorine substitution on the quinoline ring, and its PLλ _max is 614 nm. The CIE data of the device also proves that it can achieve deep red emission. The device efficiency reaches 24.28%, which proves that fluorine substitution also has a good effect.

In summary, the metal complex according to the present invention can effectively adjust the emission color to deep red, improve the external quantum efficiency of the device while maintaining a narrow full width at half maximum, and provide better device performance.

It should be understood that the various embodiments described herein are illustrative only and are not intended to limit the scope of the invention. As such, it will be apparent to one of ordinary skill in the art that the invention sought to be protected includes variations of the specific and preferred embodiments described herein. Other materials and structures can be substituted for many of the materials and structures described herein without departing from the spirit and scope of the invention. It should be understood that the various theories as to why the invention works are not limiting.

Claims (30)

A metal complex having a maximum emission wavelength of 612 nm or more in a photoluminescence spectrum (PL),
The metal complex has a structure of M(L _a ) _m (L _b ) _n , where the metal M is selected from Ir;
L _a and L _b are a first ligand and a second ligand of the complex, respectively, m is selected from 1 or 2, n is selected from 1 or 2, and m+n is equal to the oxidation state of the metal M, and when m is greater than 1, the L _a 's may be the same or different, and when n is 2, the two L _b 's may be the same or different, and L _a has a structure represented by formula 2.

Z is selected from O;
X ₃ to X ₈ are each identically or differently selected from C or CR _x at each occurrence;
Y ₁ to Y ₆ are each identically or differently selected from CR _y1 or CR _y2 at each occurrence;
Y ₄ is selected from CR _y1 , and said R _y1 is fluorine; or at least one of Y ₂ and Y ₄ is selected from CR _y2 , and said R _y2 has a structure of -L-SiR _s1 R _s2 R _s3 ;
R _x and R _y1 each occur the same or different and are selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and combinations thereof;
R _s1 , R _s2 and R _s3 each occur the same or different and are selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms;
L is selected from a single bond;
adjacent substituents R _x , R _s1 , R _s2 and R _s3 may be bonded to form a ring;
_Lb has a structure represented by the following formula:

R ₁ to R ₇ , at each occurrence, are the same or different and are selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, and combinations thereof;
Adjacent substituents R ₁ , R ₂ , R ₃ , R ₄ , R ₅ and R ₆ may be bonded to form a ring. 2. The metal complex of claim 1, wherein _Lb has a structure represented by the following formula:

(R ₁ -R ₇ at each occurrence are the same or different and are selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, and combinations thereof.) The metal complex according to claim 1, wherein at least one or two of R ₁ to R ₃ are selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a combination thereof, and/or at least one of R ₄ to R ₆ is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a combination thereof. 2. The metal complex according to claim 1, wherein at least two of R ₁ to R ₃ are selected from a substituted or unsubstituted alkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms , or a combination thereof, and/or at least two of R ₄ to R ₆ are selected from a substituted or unsubstituted alkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms , or a combination thereof. Y ₁ to Y ₆ are each the same or different and selected from CR _y1 or CR _y2 , and at least one of Y ₂ and Y ₄ is selected from CR _y2 , said R _y2 having the structure -L-SiR _s1 R _s2 R _s3 ;
R _y1 , each occurrence being the same or different, is selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, and combinations thereof;
R _s1 , R _s2 and R _s3 each occur the same or different and are selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms;
L is selected from a single bond;
The metal complex according to claim 1 , wherein adjacent substituents R _s1 , R _s2 and R _s3 may be bonded to form a ring. The metal complex according to claim 1, wherein at least two or three of X ₃ to X ₈ and Y ₁ to Y ₆ are selected from CR _x and/or CR _y1 , and each occurrence of R _x and R _y1 is the same or different and 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, and combinations thereof. The metal complex has the structure M(L _a ) _m (L _b ) _n , where the metal M is selected from Ir;
L _a and L _b are a first ligand and a second ligand of the complex, respectively, m is selected from 1 or 2, n is selected from 1 or 2, and m+n is equal to the oxidation state of the metal M, and when m is greater than 1, multiple L _a may be the same or different, and when n is 2, two L _b may be the same or different, and L _a has a structure represented by formula '2. A metal complex.

Z is selected from O, S or Se;
X ₃ to X ₈ are each identically or differently selected from C or CR _x at each occurrence;
Y ₁ to Y ₆ are each the same or different and selected from CR _y1 or CR _y2 , and at least one of Y ₂ and Y ₄ is selected from CR _y2 , said R _y2 having the structure -L-SiR _s1 R _s2 R _s3 ;
R _x and R _y1 each occur the same or different and are selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and combinations thereof;
R _s1 , R _s2 and R _s3 each occur the same or different and are selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms;
L is selected from a single bond;
adjacent substituents R _x , R _s1 , R _s2 and R _s3 may be bonded to form a ring;
_Lb has a structure represented by the following formula:

R ₁ to R ₇ , at each occurrence, are the same or different and are selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, and combinations thereof;
Adjacent substituents R ₁ , R ₂ , R ₃ , R ₄ , R ₅ and R ₆ may be bonded to form a ring.
) 8. The metal complex according to claim 1 or 7, wherein _X3 is selected from _CRx , and _Rx is selected from deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, and combinations thereof. 8. The metal complex according to claim 1 or 7, wherein at least one of X ₃ to X ₈ and Y ₁ to Y ₆ is selected from CR _x or CR _y1 , and each occurrence of R _x and R _y1 is the same or different and 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, and combinations thereof. The metal complex according to claim 7, wherein at least two or three of X ₃ to X ₈ and Y ₁ to Y ₆ are selected from CR _x and/or CR _y1 , and each occurrence of R _x and R _y1 is the same or different and 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, and combinations thereof. The metal complex according to claim 7 , wherein L _a has a structure represented by formula 2:

Z is selected from O, S or Se;
X ₃ to X ₈ are each identically or differently selected from CR _x at each occurrence;
Y ₁ to Y ₆ are each the same or different and selected from CR _y1 or CR _y2 , and at least one of Y ₂ and Y ₄ is selected from CR _y2 , said R _y2 having the structure -L-SiR _s1 R _s2 R _s3 ;
R _x and R _y1 each occur the same or different and are selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms , and combinations thereof;
R _s1 , R _s2 and R _s3 each occur the same or different and are selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms;
L is selected from a single bond;
Adjacent substituents R _x , R _s1 , R _s2 and R _s3 may be bonded to form a ring. Y ₁ to Y ₂ are each the same or different and selected from CR _y1 , Y ₃ to Y ₆ are each the same or different and selected from CR _y1 or CR _y2 , and Y ₄ is selected from CR _y2 , said R _y2 having the structure -L-SiR _s1 R _s2 R _s3 ;
R _y1 is, at each occurrence, the same or different, selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and combinations thereof;
R _s1 , R _s2 and R _s3 each occur the same or different and are selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms;
L is selected from a single bond;
12. The metal complex according to claim 1, wherein adjacent substituents R _s1 , R _s2 and R _s3 may be bonded to form a ring. 8. The metal complex of claim 1 or 7, wherein the metal complex has a structure represented by Formula 3:

m is 1 or 2,
Z is O;
X ₃ to X ₈ are each identically or differently selected from CR _x at each occurrence;
Y ₁ to Y ₆ are each the same or different and selected from CR _y1 or CR _y2 , and at least one of Y ₂ and Y ₄ is selected from CR _y2 , said R _y2 having the structure -L-SiR _s1 R _s2 R _s3 ;
R _x and R _y1 each occur the same or different and are selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and combinations thereof;
R _s1 , R _s2 and R _s3 each occur the same or different and are selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms;
L is selected from a single bond;
R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , and R ₇ are each the same or different and are selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, and combinations thereof;
adjacent substituents R _x , R _s1 , R _s2 and R _s3 may be bonded to form a ring;
Adjacent substituents R ₁ , R ₂ , R ₃ , R ₄ , R ₅ and R ₆ may be bonded to form a ring. The metal complex according to claim 13, wherein at least one or two of R ₁ to R ₃ are selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms , or a combination thereof, and/or at least one of R ₄ to R ₆ is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms , or a combination thereof. The metal complex according to claim 13, wherein at least two of R ₁ to R ₃ are selected from a substituted or unsubstituted alkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms , or a combination thereof, and/or at least two of R ₄ to R ₆ are selected from a substituted or unsubstituted alkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms , or a combination thereof. X ₃ to X ₈ are each independently selected from CR _x ;
The metal complex according to any one of claims 7 to 15, wherein R _x is selected from hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a combination thereof. 16. The metal complex according to claim 7, wherein _X3 is selected from _CRx , and _Rx is selected from hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a combination thereof. 18. The metal complex according to claim 17 , wherein _X3 is selected from _CRx , wherein _Rx is selected from deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a combination thereof. One of Y2 and Y4 _is selected from CR _{y2 ,} where R _y2 has the structure -L-SiR _s1 R _s2 R _s3 ;
The metal complex according to any one of claims 7 to 17 , wherein L is selected from a single bond, and R _s1 , R _s2 and R _s3 are each independently selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. At least one of Y2 and Y4 _is selected from CR _{y2 ,} where R _y2 has the structure -L-SiR _s1 R _s2 R _s3 ;
wherein L is selected from a single bond, and R _s1 , R _s2 and R _s3 are each independently selected from the group consisting of a methyl group, an ethyl group, an isopropyl group, an isobutyl group, a tert-butyl group, a neopentyl group , a cyclopentylmethyl group , a trifluoromethyl group and combinations thereof;
The metal complex according to any one of claims 7 to 16 . L _a is the same or different for each occurrence, L _{a 1} to L a ₁₀₈ , L _{a 133} to L _{a 231} , L _{a 254} to L _{a 297} , L _{a 320} to L _{a 363} , L _{a 484} to L _{a 531} , L _{a 556} to L _{a 603} , L _{a 712} to L _{a 726} , L _{a 728} to L a ₇₇₅ , L _{a 800} to L _{a 835} , L _{a 980} to L _{a 1027} , L _{a 1052} to L a ₁₀₉₉ , L a ₁₁₉₆ to L _{a 1212} , L _{a 1430} to L _{a 1459} , L _{a 1466} to L _{a 1477} , L _{a 1484} to L _{any one selected from the group consisting of L a1} to _{L a108} , L _a133 to L _a231 , L _a254 to L _{a297 ,} L _a320 to L _a363 , L _a484 to L _a531 ​ _​ ​ _​ ​ _{​ ​ ​ ​ ​} ​ _​ ​, L _a556 - L _a603 , L _a712 - L _a726 , L _a728 - L _a775 , L _a800 - L _a835 , L _a980 - L _a1027 , L _a1052 - L _a1099 , L _a1196 - L _a1212 , L _a1430 ~ L _a1459 , L _a1466 ~ L _a1477 , L _a1484 ~ L _a1489 , L _a1496 ~ L _a1501 , L _a1508 ~ L _a1521 , L _a1523 ~ L _a1526 , L _a1528 ~ L _a1547 , L _a1556 ~ L 8. The metal complex according to claim 1, wherein specific structures of L _a1557 , L _a1566 to L _a1569 , L _a1578 to L _a1581 , L _a1590 to L _a1597 , and L _a1604 to L _a1607 are represented as follows:

(L _a1 to L _a108 , L _a133 to L _a231 , L _a254 to L _a297 , L _a320 to L _a363 , L _a484 to L _a531 , L _a556 to L _a603 , L _a712 to L _a726 , L _a728 to L _a775 , L _a800 to L _a835 , L _a980 to L _a1027 , L _a1052 to L _a1099 , L _a1196 to L _a1212 , L _a1430 to L _a1459 , L _a1466 to L _a1477 , L _a1484 to L _a1489 , and L In the structures of _a1496 to L _a1501 , R ^a1 to R ^a9 are the following groups, respectively.

The metal complex according to any one of claims 1 to 21 , wherein _Lb is the same or different at each occurrence and is selected from the following structures:

(R ₁ to R ₇ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted cycloalkyl group having 4 to 10 ring carbon atoms, and combinations thereof;
Adjacent substituents R ₁ , R ₂ , R ₃ , R ₄ , R ₅ and R ₆ may be bonded to form a ring. The metal complex according to any one of claims 1 to 22 , wherein _Lb each occurrence is the same or different and is any one selected from the group consisting of the following structures:

The metal complex has the structure Ir(L _a ) ₂ (L _b ),
When the metal complex has the structure of Ir(L _a ) ₂ (L _b ), L _a is, each occurrence, the same or different, L _a1 to L _a108 , L _a133 to L _a231 , L _a254 to L _a297 , L _a320 to L _a363 , L _a484 to L _a531 , L _a556 to L _a603 , L _a712 to L _a726 , L _a728 to L _a775 , L _a800 to L _a835 , L _a980 to L _a1027 , L _a1052 to L _a1099 , L _a1196 to L _a1212 , L _a1430 to L _a1459 , L L _a1466 to L _a1477 , L _a1484 to L _a1489 , L _a1496 to L _a1501 , L _a1508 to L _a1521 , L a1523 _to L _a1526 , L _a1528 to L _a1547 , L _a1556 to L _a1557 , L _a1566 to L _a1569 , L _a1578 to L _a1581 , L _a1590 to L _a1597 , and L _a1604 to L _a1607 , and L _b is any one or two selected from the group consisting of L _b1 to L _b235 , L _b240 to L The metal complex according to claim 23 , which is any one selected from the group consisting of _: The metal complexes are selected from the group consisting of Compound 1 to Compound 9, Compound 14 to Compound 16, Compound 19 to Compound 21, Compound 30, Compound 32, Compound 34 to Compound 35, Compound 37 to Compound 45, Compound 50 to Compound 52, Compound 55 to Compound 57 , Compound 66, Compound 68, Compound 70 to Compound 71, Compound 73 to Compound 81, Compound 86 to Compound 88 , Compound 91 to Compound 93, Compound 102, Compound 104, Compound 106 to Compound 107, Compound 109 to Compound 117, Compound 122 to Compound 124, Compound 127 to Compound 129 , Compound 138, Compound 140, Compound 142 to Compound 143, Compound 145 to Compound 153, Compound 158 to Compound 160, Compound 163 to Compound 165, Compound 174, Compound 176 , Compound 178 to Compound 179, Compound 181 to Compound 189, and Compound 194. ~ Compound 196, Compound 199 ~ Compound 201 , Compound 210, Compound 212, Compound 214 ~ Compound 215 , Compound 217 ~ Compound 218, Compound 220 ~ Compound 223, Compound 225 , Compound 227, Compound 229, Compound 231 ~ Compound 232, Compound 235 ~ Compound 237, Compound 239 , Compound 24 1, Compound 243, Compound 245 to Compound 246, Compound 248 to Compound 251, Compound 253 , Compound 255, Compound 257, Compound 259 to Compound 260, Compound 262 to Compound 265, Compound 267 , Compound 269, Compound 271, Compound 273 to Compound 274, Compound 276 to Compound 279, Compound 281 , Compound 283, Compound 285 , Compound 287 ~ Compound 288, Compound 290 ~ Compound 293, Compound 295 24. The metal complex according to claim 23 , which is selected from the group consisting of Compound 297, Compound 299, Compound 301 to Compound 308, Compound 311, Compound 315 to Compound 316.
(Compound 1 to Compound 9, Compound 14 to Compound 16, Compound 19 to Compound 21, Compound 24 to Compound 25, Compound 30, Compound 32, Compound 34 to Compound 35, Compound 37 to Compound 45, Compound 50 to Compound 52, Compound 55 to Compound 57, Compound 66, Compound 68, Compound 70 to Compound 71 , Compound 73 to Compound 81, Compound 86 to Compound 88, Compound 91 to Compound 93 , Compound 102, Compound 104 , Compound 106 to Compound 107, Compound 109 to Compound 117, Compound 122 to Compound 124, Compound 127 to Compound 129 , Compound 138, Compound 140, Compound 142 to Compound 143, Compound 145 to Compound 153, Compound 158 to Compound 160 , Compound 163 to Compound 165 , Compound 174, Compound 176, Compound 178 Compounds 179 to 189, Compounds 194 to 196, Compounds 199 to 201 , Compound 210, Compound 212, Compounds 214 to 215, and Compounds 301 to 308, Compound 311, and Compounds 315 to 316 have a structure of Ir(L _a ) ₂ (L _b ), in which two L _a's are the same, and L _a and L _b are each selected from the structures listed in the following table:

Compounds 217 to 218, Compounds 220 to 223, Compound 225, Compound 227 , Compound 229, Compounds 231 to 232, Compounds 235 to 237, Compound 239, Compound 241, Compound 243, Compounds 245 to 246, Compounds 248 to 251, Compound 253, Compound 255 , Compound 257, Compound 259 to 260, Compounds 262 to 265, Compound 267, Compound 269, Compound 271, Compounds 273 to 274, Compounds 276 to 279, Compound 281, Compound 283, Compound 285, Compounds 287 to 288, Compounds 290 to 293, Compound 295, Compound 297, and Compound 299 each have a structure of Ir(L _a ) ₂ (L _b ), in which two L _{a 's} are different, and L _a and _Lb are each selected from the structures listed in the table below.

An anode;
A cathode;
an organic layer disposed between the anode and the cathode,
An electroluminescent device, wherein the organic layer comprises a metal complex according to any one of claims 1 to 25 . 27. The device of claim 26 , wherein the organic layer is an emissive layer and the metal complex is an emissive material. 27. The device of claim 26 , wherein the electroluminescent device emits red or white light. The light-emitting layer further comprises at least one host material,
28. The device of claim 27, wherein the at least one host material comprises at least one chemical group selected from the group consisting of benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazolyl, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorenyl, silicon fluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof. A composition comprising the metal complex according to any one of claims 1 to 25 .

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