JP2021191744A - Organic light emitting material - Google Patents

Abstract

To provide an organic light emitting material, which can effectively adjust a light-emitting color to deep red, can improve external quantum efficiency of devices while maintaining a relatively narrow FWHM (full width at half maximum), and can provide better device performance.SOLUTION: Specifically, a novel Ir metal complex synthesized, for example, according to the following equation is used as an organic light emitting material.SELECTED DRAWING: None

Description

The present invention relates to compounds used in organic electronic devices such as organic light emitting devices. More particularly, the present invention relates to a metal complex containing a ligand having a structure represented by the formula 1 or the formula 1', and an electroluminescent device and a compound containing the metal complex.

Organic electronic devices include organic light emitting diodes (OLEDs), organic field effect transistors (O-FETs), organic light emitting transistors (OLETs), organic electromotive cells (OPVs), dye-sensitized solar cells (DSSCs), and organic light detection. It includes, but is not limited to, an instrument, an organic photosensitive device, an organic field effect element (OFQDs), a light emitting electrochemical cell (LECs), an organic laser diode, and an organic plasma light emitting element.

In 1987, by Tang and Van Slyke of Eastman Kodak, a two-layer organic electroluminescent layer containing an arylamine hole transport layer and a tris-8-hydroxyquinoline-aluminum layer as electron transport layers and light emitting layers. The element has been reported (Applied Physics Letters, 1987, 51 (12): 913-915 (Non-Patent Document 1)). Once a bias is applied to the device, green light is emitted from the device. This invention lays the foundation for the development of modern organic light emitting diodes (OLEDs). The most advanced OLEDs may include multiple layers such as a charge injection / transport layer, a charge / exciton blocking layer, and one or more light emitting layers between the cathode and the anode. Since OLEDs are self-luminous solid-state devices, they offer enormous potential for display and lighting applications. Also, the unique properties of organic materials, such as their flexibility, are very suitable for special applications such as manufacturing performed on flexible substrates.

OLEDs are divided into three different types according to their light emitting mechanism. The OLED invented by Tang and van Slyke is a fluorescent OLED and uses only singlet emission. This limitation hinders the commercialization of OLEDs, as the triplet generated in the device is wasted by the non-radiative attenuation passage and the internal quantum efficiency (IQE) of the fluorescent OLED is only 25%. In 1997, Forest and Thompson reported a phosphorescent OLED that uses triplet emission from a complex-containing heavy metal as a light emitter. Therefore, singlet and triplet can be harvested and 100% IQE can be achieved. Due to its high efficiency, the discovery and development of phosphorescent OLEDs will directly contribute to the commercialization of active matrix OLEDs (AMOLEDs). Recently, Adachi has achieved high efficiency through thermal activated delayed fluorescence (TADF) of organic compounds. These illuminants have a small singlet-triplet gap, allowing excitons to transition back from triplet to singlet. In TADF devices, IQE is high due to the generation of singlet excitons by the penetration of triplet excitons between reverse systems (intersystem crossing).

OLEDs may be further divided into small molecules and polymer OLEDs, depending on the form of the required material. The small molecule refers to a material that is not a polymer and is either organic or organometallic, and may have a large molecular weight as long as it has an accurate structure. Dendrimers with a well-defined structure are recognized as small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with side chain light emitting groups. When post-polymerization occurs in the manufacturing process, small molecule OLEDs can become polymer OLEDs.

Various methods for manufacturing OLEDs are known. Small molecule OLEDs are generally manufactured by vacuum thermal evaporation. Polymer OLEDs are manufactured by solution methods such as spin coating, inkjet printing and nozzle printing. Small molecule OLEDs can also be produced by the solution method if the material is capable of dissolving or dispersing in a solvent.

The emission color of the OLED can be realized by the structural design of the emission material. The OLED may include one or more light emitting layers to achieve the desired spectrum. In green, yellow, and red OLEDs, phosphorescent materials have already succeeded in commercialization, but blue phosphorescent elements still have problems such as blue saturation, short life, and high working voltage. Exists. Commercially available full-color OLED displays generally use a mixing strategy, with blue fluorescence and yellow, red or green phosphorescence. At present, there is a problem that the efficiency of phosphorescent OLED rapidly decreases when the brightness is high. It is also desired to have a more saturated emission spectrum, higher efficiency, and longer device life.

The phosphorescent metal complex has been applied in the field of organic electroluminescence lighting or display as a phosphorescent doping material in a light emitting layer. By adjusting different substituents in the ligand of the material to meet the needs of different cases, it is possible to realize the adjustment to the complexion of the material on a certain basis and obtain phosphorescent metal complexes having different emission wavelengths. ..

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。

Of which, a series

And has a similar structure. The applicant of the invention points out that the material of the structure has high EL efficiency and good service life, but is devoted to the study of application of dinitrogen ligand containing diazole / triazole in metal complexes. while, the R ¹ group substituted on the particular ring is not focused on the advantages of a silyl group.

CN1079733823A (Patent Document 2) discloses a compound having a quinolinyl dibenzo substitution as a ligand.

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, an alkyl group, a heteroalkyl group, an aryl group or a heteroaryl group. The invention Applicants have material good stability of the structure, will be pointed out to have a useful life and complexion saturation, substituents R ₁ to R ₄ in the disclosed structure are each hydrogen or an alkyl group And the advantages of having a silyl substituent on a particular ring have not been disclosed or suggested.

Despite the existence of metal complexes with quinoline-structured ligands, their related performance, such as luminescent complexion, device efficiency, and device useful life, is still lacking, and research on related materials is underway. , Still need to dig deeper.

Chinese Patent Application Publication No. 104335377 Chinese Patent Application Publication No. 109783823

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

An object of the present invention is to provide a metal complex containing a ligand having a structure represented by the formula 1 or the formula 1'in order to solve at least a part of the above-mentioned problems. 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. Can be done.

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

（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 selected from _{C, CR x} or N, which are the same or different for each appearance.
Y _{1 to Y 6 are selected from CR y} or N, which are the same or different for each appearance.
R _x and R _y are the same or different each time they appear, such as hydrogen, dehydrogen, halogen, an alkyl group having 1 to 20 substituted or unsubstituted carbon atoms, and a cyclo having 3 to 20 substituted or unsubstituted ring carbon atoms. Alkyl group, substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted Or an unsubstituted 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, substituted or unsubstituted. Heteroaryl group with 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group with 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group with 6 to 20 carbon atoms, substituted or unsubstituted carbon atom Selected from the group consisting of an amine group, 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 a combination thereof. ,
Adjacent substituents R _x may be bonded to form a ring. )

According to one embodiment of the present invention, the metal relative atomic mass of the metal complex is selected from 40 than the metal, containing a ligand L _a having the structure represented by Formula 1 ', the metal complexes is disclosed To.

（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 selected from _{C, CR x} or N, which are the same or different for each appearance.
Y ₁ to Y ₆ are the same or different at each occurrence selected from _CR y1, _{CR y2} or N, and at least one of _Y 1 to Y ₆ is selected from _{CR y2,} wherein _{R y2} is -L-SiR _s1 R _s2 R _s3 structure,
R _x , R _y1 , R _s1 , R _s2 , and R _s3 are the same or different at each appearance, hydrogen, dehydrogen, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted. Cycloalkyl group with 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl group with 1 to 20 carbon atoms, substituted or unsubstituted aralkyl group with 7 to 30 carbon atoms, substituted or unsubstituted carbon atom An alkoxy group having 1 to 20, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, an alkenyl group having 2 to 20 substituted or unsubstituted carbon atoms, and 6 to 30 substituted or unsubstituted carbon atoms. Aryl group, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms. Group, substituted or unsubstituted amine group with 0 to 20 carbon atoms, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxyl group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group and Selected from the group consisting of these combinations
L is a single-bonded, substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, or substituted or unsubstituted arylene having 6 to 20 carbon atoms. Selected from the group consisting of groups, substituted or unsubstituted heteroarylene groups having 3 to 20 carbon atoms, or combinations thereof.
Adjacent substituents R _x , R _s1 , R _s2 , and R _s3 may be combined to form a ring. )

According to another embodiment of the present invention, the electroluminescent device includes a positive, a cathode, and an organic layer provided between the anode and the cathode, and the organic layer has a specific structure. Further discloses an electroluminescent device comprising a metal complex as shown in any one of the embodiments described above.

According to other embodiments of the invention, formulations of compounds containing metal complexes as described above are further disclosed.

A novel metal complex containing a ligand having the structure of the formula 1 or the formula 1'according to the present invention can be used as a light emitting material in an 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. Can be done.

It is a schematic diagram of the organic light emitting device which may contain the formulation of the metal complex and compound which concerns on this invention. It is a schematic diagram of another organic light emitting device which may contain the formulation of the metal complex and compound which concerns on this invention.

OLEDs can be manufactured from a variety of substrates such as glass, plastic, and metal. FIG. 1 illustrates the organic light emitting device 100 without limitation. It is not always manufactured according to the scale of the drawing, and some layer structures may be omitted in the drawing if necessary. The apparatus 100 includes a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190. May be included. The device 100 may be manufactured by sequentially depositing the described layers. The properties, functions, and exemplary materials of each layer are described in more detail in US Pat. No. 6,279,704B2, columns 6-10, the entire contents of which are incorporated herein by reference.

There are more examples in each of these layers. Illustratively, US Pat. No. 5,844,363, incorporated with reference to the full text, discloses a flexible, transparent substrate-anode combination. For example, in U.S. Patent Application Publication No. 2003/0230980, which is incorporated as incorporated the full text, the examples of the hole transport layer of the p-type doped 50: _F 4 -TCNQ is doped at a molar ratio of m- It is disclosed that it is MTDATA. An example of a host material is disclosed in US Pat. No. 6,303,238 by Thompson et al., Incorporated with full text. For example, in U.S. Patent Application Publication No. 2003/0230980 incorporated with reference to the full text, it is disclosed that an example of an n-type doped electron transport layer is a Li-doped BPhen in a 1: 1 molar ratio. Has been done. In US Pat. Nos. 5,703,436 and 570,745, which are incorporated to be incorporated in full text, they have a thin metal layer, such as Mg: Ag, and a transparent, sputter-deposited, conductive ITO layer coated on it. Examples of cathodes, including composite cathodes, are disclosed. U.S. Patent No. 6097147 and U.S. Patent Application Publication No. 2003/0230980, incorporated to be incorporated in full text, describe in more detail the principles and use of blocking layers. An example of an infusion layer is provided in US Patent Application Publication No. 2004/0174116, which has been incorporated with reference to the full text. The protective layer is described in U.S. Patent Application Publication No. 2004/0174116, which has been incorporated with reference to the full text.

Non-limiting examples provide the layered structure described above. The function of the OLED can be realized by combining the various layers described above, or some layers can be completely omitted. It may include other layers that are not explicitly stated. Within each layer, a single material or a mixture of various materials can be used to achieve optimum performance. Each functional layer may include a plurality of sublayers, for example, the light emitting layer may have two different light emitting materials so as to achieve a desired emission spectrum.

In one embodiment, the OLED may be described as having an "organic layer" provided between the cathode and the anode. The organic layer may include one or more layers.

The OLED also requires an encapsulation layer, and as shown in FIG. 2, the organic light emitting device 200 is shown without limitation. The difference from FIG. 1 is that the encapsulation layer 102 may be included on the cathode 190 so as to prevent harmful substances from the outside world such as water and oxygen. Any material capable of providing encapsulation function, such as glass or an organic-inorganic mixed layer, may be used as the encapsulation layer. The encapsulation layer should be placed directly or indirectly outside the OLED device. Multilayer thin film encapsulation is described in US Pat. No. 6,968,146B2, the entire contents of which are incorporated herein by reference.

The device manufactured according to the embodiment of the present invention may be incorporated into various consumer products having one or more electronic member modules (or units) of the device. These consumer products include, for example, flat panel displays, monitors, medical monitors, televisions, billboards, indoor or outdoor lighting lamps and / or signal lamps, head-up displays, all or part transparent displays, flexible Includes displays, smartphones, flat panel computers, flat panel mobile phones, wearable elements, smart watches, laptop computers, digital cameras, portable video cameras, finder, microdisplays, 3-D displays, in-vehicle displays and taillights.

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

The "top" means the furthest from the substrate and the "bottom" means the closest to the substrate. When it is stated that the first layer is provided "above" the second layer, the first layer is provided so as to be relatively far from the substrate. Other layers may be present between the first layer and the second layer, as long as the first layer does not specify that it "contacts" the second layer. Illustratively, it can be stated that the cathode is still provided "on" the anode, even though various organic layers are present between the cathode and the anode.

"Solution is processable" means that it can be dissolved, dispersed or transported in a liquid medium in the form of a solution or suspension and / or deposited from the liquid medium.

It is believed that ligands may be referred to as "photosensitive" if they directly promote the photosensitive properties of the propellant. The ligand may be referred to as "auxiliary" if it does not promote the photosensitive properties of the propellant. However, it is believed that auxiliary ligands can alter the properties of photosensitive ligands.

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 generally be divided into two types, namely P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is produced by triplet-triplet annihilation (TTA).

On the other hand, E-type delayed fluorescence depends on the conversion of the excited state between the triplet and the singlet, not the collision of the two triplets. Compounds capable of producing E-type delayed fluorescence are required to have a very small singlet-triplet gap to perform energy state conversions. Thermal energy can activate the transition from triplet to singlet. This type of delayed fluorescence is also referred to as Thermally Activated Delayed Fluorescence (TADF). A salient feature of TADF is that the delayed component improves with increasing temperature. When the velocity of penetration between reverse systems (RISCs) (intersystem crossing) is fast enough, the non-radiative attenuation from the triplet is minimized and the proportion of excited states of the backfilled singlet reaches 75%. Can be done. The total percentage of singlets may be 100%, well above 25% of the electroexciton spin statistics.

The characteristics of E-type delayed fluorescence are visible from the excited complex system or a single compound. Not limited by theory, E-type delayed fluorescence is singlet light-emitting material is small - it is necessary to have a triplet energy gap (ΔE _S-T). Donor / acceptor luminescent materials containing organic non-metals may achieve this. Launches of these materials are usually characterized as donor-receptor charge transition (CT) -type launches. In these donor-acceptor type compounds, spatial separation between the HOMO and the LUMO will produce generally small Delta] E _S-T. These states may include CT states. Usually, the donor / acceptor luminescent material is constructed by binding an electron donor moiety (eg, an amine group or a carbazole derivative) to an electron acceptor moiety (eg, an N-containing six-membered aromatic ring).

Definition of technical terms for substituents

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

Alkyl groups include straight-chain and branched-chain alkyl groups, as used herein. 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 are 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-Butyl Pentyl, 1-Heptyl Octyl, and 3-Methyl Pentyl. Further, the alkyl group may be substituted. The carbon in the alkyl base chain may be substituted with another heteroatom. Of these, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl and n-hexyl are preferred. Further, the alkyl group may be substituted.

Cycloalkyl groups include cyclic alkyl groups, as used herein. The cycloalkyl group may be a cycloalkyl group having 3 to 20 carbon atoms, and is preferably a cycloalkyl group having 4 to 10 carbon atoms. Examples of cycloalkyl groups include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl group, 2-norbornyl group and the like. Of these, cyclobutyl, cyclopentyl, 4-methylcyclohexyl, and 4,4-dimethylcyclohexyl are preferably contained. Further, the cycloalkyl group may be substituted.

As used herein, a heteroalkyl group consists of one or more carbons in an alkyl chain consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a phosphorus atom, a silicon atom, a germanium atom and a boron atom. Includes those substituted with heteroatoms selected from the group. 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 a heteroalkyl group having 1 to 6 carbon atoms. Is more preferable. Examples of heteroalkyl groups are oxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl group, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, sulfanyl. Methyl, sulfanylethyl, sulfanylpropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, tert-butyltriethylsilyl, triisopropylsilyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl include. Further, the heteroalkyl group may be substituted.

Alkene groups include straight chain, branched chain and cyclic olefin groups as used herein. The chain alkenyl group may be an alkenyl group having 2 to 20 carbon atoms, and is preferably an alkenyl group having 2 to 10 carbon atoms. Examples of alkenyl groups are 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. Further, the alkenyl group may be substituted.

The alkynyl group includes a linear alkynyl group as used herein. The alkynyl group may be an alkynyl group having 2 to 20 carbon atoms, and is preferably an alkynyl group having 2 to 10 carbon atoms. Examples of alkynyl groups are ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3,3-dimethyl-1-butynyl, 3-ethyl-3-methyl-. It contains 1-pentynyl, 3,3-diisopropyl1-pentynyl, phenylethynyl, phenylpropynyl and the like. As described above, it is preferable to include ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, phenylethynyl. Further, the alkynyl group may be substituted.

Aryl or aromatic groups are considered non-condensed and condensed systems as used herein. 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, including phenyl, biphenyl, terphenyl, triphenylene, fluorenyl and It preferably contains naphthalene. Further, the aryl group may be substituted. Implementation of non-condensed aryl groups is phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-tribiphenyl. -2-yl, m-Phenyl-4-yl, m-Phenyl-3-yl, m-Phenyl-2-yl, o-tryl, m-trill, p-trill, p- (2-phenylpropi) Le) Phenyl, 4'-methylbiphenyl, 4''-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-kisilyl, 3,4-kisilyl , 2,5-Dimethylphenyl, Mesitylen and m-Tetraphenyl. Further, the aryl group may be substituted.

The heteroaryl group may include non-condensed and condensed heteroaromatic groups having 1 to 5 heteroatoms, as used herein. At least one of these heteroatoms is selected from the group consisting of nitrogen atom, oxygen atom, sulfur atom, selenium atom, silicon atom, phosphorus atom, germanium atom and boron atom. The isoaryl group also refers to a heteroaryl group. The heteroaryl group may be a heteroaryl group having 3 to 30 carbon atoms, preferably a heteroaryl group having 3 to 20 carbon atoms, and a heteroaryl group having 3 to 12 carbon atoms. Is more preferable. Suitable heteroaryl groups are dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridoindole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, Thiazol, Oxazole, Oxazole, Dioxazole, Thiasiazol, Pyridine, Pyridazine, Pyrimidine, Pyrazine, Triazine, Oxazole, Oxazole, Oxazole, Indol, Benzimidazole, Indazole, Indenoazine, Benzoxazole, Benzisoxazole, Benzothazole, Kinolin , Isoquinoline, Synnoline, Kinazoline, Kinoxalin, Naftilidine, Phthalazine, Pteridine, Xanthene, Acrydin, Phenazine, Phenothiazine, Benzofuranpyridine, Frosipyridine, Benzothienopyridine, Thienobipyridine, Benselenopyridine, and Serenebenzopyridine, including dibenzothiophene, dibenzofuran, It preferably contains dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborane, 1,3-azaborane, 1,4-azaborane, borazole and its aza analogs. Further, the heteroaryl group may be substituted.

The alkoxy group is represented by an -O-alkyl group, an -O-cycloalkyl group or an -O-heteroalkyl group as used herein. Examples and suitable examples of alkyl groups, cycloalkyl groups and heteroalkyl groups are similar to 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 alkoxy groups include methoxy, ethoxy, propoxy, butoxy, pentoxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy and ethoxymethyloxy. .. Further, the alkoxy group may be substituted.

Aryloxy groups are represented by -O-aryl groups or -O-heteroaryl groups as used herein. Examples and preferred examples of aryl and heteroaryl groups are similar to 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 aryloxy groups include phenoxy and biphenoxy groups. Further, the aryloxy group may be substituted.

The aralkyl group includes an alkyl group substituted with an aryl group as used herein. 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 are benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl-tert-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-. Naftylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthyl-ethyl, 2-β-naphthyl-ethyl, 1-β-naphthylisopropyl, 2-β-naphthyl. Isopropyl, p-methylbenzyl, m-methylbenzyl, o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl, o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodo Benzyl, m-iodobenzyl, o-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-hydroxybenzyl, p-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitro Includes benzyl, 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. Further, the aralkyl group may be substituted.

The alkylsilyl group includes a silyl group substituted with an alkyl group as used herein. 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-butylsilicon, triisobutylsilyl, Includes dimethyl-tert-butylsilyl and methyldi-tert-butylsilyl. Further, the alkylsilyl group may be substituted.

Arylsilyl groups include silyl groups substituted with at least one aryl group, as used herein. 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 are triphenylsilyl, phenyldiphenylsilyl, diphenylbiphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl. , Diphenyl-tert-butylsilyl, tri-tert-butylsilyl, dimethyl-tert-butylsilyl, and methyldi-tert-butylsilyl. Further, the arylsilyl group may be substituted.

"Aza" in azadibenzofuran, azadibenzothiophene, etc. refers to the substitution of one or more CH groups in the corresponding aromatic fragment with a nitrogen atom. For example, azatriphenylenes include dibenzo [f, h] quinoxaline, dibenzo [f, h] quinoline, and other analogs with two or more nitrogens in the ring system. Those skilled in the art can easily conceive of other nitrogen analogs of the above-mentioned bruises derivatives, and all of these analogs are established as included in the terminology described herein. ..

In the present invention, unless otherwise specified, 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, and a substituted alkenyl group. Alkinyl 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 , An alkyl group, a cycloalkyl group, a heteroalkyl group, an aralkyl group, an alkoxy group, an aryloxy group, using any of the terms in the group consisting of a substituted sulfinyl group, a substituted sulfonyl group, and a substituted phosphino group. Any of 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. Groups are heavy hydrogen, halogen, alkyl groups with 1 to 20 unsubstituted carbon atoms, cycloalkyl groups with unsubstituted 3 to 20 ring carbon atoms, and 1 to 20 unsubstituted carbon atoms. Heteroalkyl groups with atoms, arylyl groups with unsubstituted 7 to 30 carbon atoms, alkoxy groups with unsubstituted 1 to 20 carbon atoms, and unsubstituted 6 to 30 carbon atoms. Aryloxy groups, alkenyl groups with unsubstituted 2 to 20 carbon atoms, alkynyl groups with unsubstituted 2 to 20 carbon atoms, aryl groups with unsubstituted 6 to 30 carbon atoms, no. Heteroaryl groups with substituted 3 to 30 carbon atoms, alkylsilyl groups with unsubstituted 3 to 20 carbon atoms, arylsilyl groups with unsubstituted 6 to 20 carbon atoms, unsubstituted One selected from an amine group, 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 a combination thereof having 0 to 20 carbon atoms. Or it means that it can be replaced by more than one.

When a molecular fragment is described as a substituent or other form of attachment to another moiety, whether it is a fragment (eg, phenyl group, phenylene group, naphthyl group, dibenzofuranyl group) or the whole molecule. It should be understood that the name can be determined by whether or not it is (eg, benzene, naphthalene, dibenzofuran). As used herein, different forms of substituent designation or fragment binding are recognized as uniform.

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

In the compounds referred to herein, multiple substitutions refer to the extent to which the most available substitutions are reached, including double substitutions. A substituent in a compound referred to herein means multiple substitutions (including double substitutions, triple substitutions, quadruple substitutions, etc.) and the substituents are available on multiple binding structures. It means that it may be present at the substitution position, and the substituent present at any of the plurality of available substitution positions may have the same structure or may have a different structure.

In the compounds referred to herein, the adjacent substituents in the compound may combine to form a ring, unless otherwise limited so that adjacent substituents may be attached to form a ring. Can not. In the compounds referred to herein, the fact that adjacent substituents may be bonded to form a ring includes the case where adjacent substituents are bonded to form a ring, and the adjacent substituents are formed. Includes the case where does not form a ring without binding. When adjacent substituents may be bonded to form a ring, the formed ring may be a monocyclic or polycyclic ring, and an alicyclic, a heteroaliphatic ring, an aryl ring, or a heteroaryl ring. .. In such a description, the adjacent substituent refers to a substituent bonded to the same atom, a substituent bonded to a carbon atom directly bonded to each other, or a substituent bonded to a further distant carbon atom. May be good. Preferably, adjacent substituents refer to substituents attached to the same carbon atom and substituents attached to carbon atoms that are directly attached to each other.

The description that adjacent substituents may be bonded to form a ring is also recognized to mean that two substituents bonded to the same carbon atom are bonded to each other by a chemical bond to form a ring. , Can be exemplified by the following formula.

The statement that adjacent substituents may be bonded to form a ring also means 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. It is recognized and can be exemplified by the following formula.

In addition, the description that adjacent substituents may be bonded to form a ring also states that the second substituent represents hydrogen when one of the two substituents bonded to the carbon atom directly bonded to each other represents hydrogen. It is recognized that it means that hydrogen atoms are bonded at the bonded positions to form a ring. It is illustrated by the following formula.

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

（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 selected from _{C, CR x} or N, which are the same or different for each appearance.
Y _{1 to Y 6 are selected from CR y} or N, which are the same or different for each appearance.
R _x and R _y are the same or different each time they appear, such as hydrogen, dehydrogen, halogen, an alkyl group having 1 to 20 substituted or unsubstituted carbon atoms, and a cyclo having 3 to 20 substituted or unsubstituted ring carbon atoms. Alkyl group, substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted Or an unsubstituted 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, substituted or unsubstituted. Heteroaryl group with 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group with 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group with 6 to 20 carbon atoms, substituted or unsubstituted carbon atom Selected from the group consisting of an amine group, 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 a combination thereof. ,
Adjacent substituents R _x may be bonded to form a ring. )

In the present specification, adjacent substituents R _x may be bonded to form a ring, which means that when a plurality of substituents R _x are present, any of the adjacent substituents R _x are bonded to form a ring. It means that it may form. Obviously, when a plurality of substituents R _x are present, any of the adjacent substituents R _x need not be combined to form a ring. Any of the adjacent substituents _Ry cannot be bonded to form a ring.

In this example, the fact that the metal complex has a maximum radiation wavelength of 612 nm or more in the photoluminescence spectrum (PL) means that the metal complex is dissolved in anhydrous dichloromethane to prepare a solution ^{having a concentration of 3 × 10 -5 mol / L.} Then, when the photoluminescence spectrum (PL) of the solution of the metal complex is measured at room temperature (298K) using a fluorescence spectrophotometer, the maximum emission wavelength of the metal complex in the photoluminescence spectrum is 612 nm or more. Point to that. 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 the 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 the _R x, _{R y} Is the same or different for each appearance, a heavy hydrogen, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, substituted or unsubstituted. Heteroalkyl groups with 1 to 20 carbon atoms, arylyl groups with 7 to 30 substituted or unsubstituted carbon atoms, alkoxy groups with substituted or unsubstituted carbon atoms 1 to 20, substituted or unsubstituted carbon atoms 6-30 aryloxy groups, substituted or unsubstituted alkenyl groups with 2 to 20 carbon atoms, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, substituted or unsubstituted carbon atoms with 3 to 30 Heteroaryl groups, substituted or unsubstituted alkylsilyl groups with 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups with 6 to 20 carbon atoms, substituted or unsubstituted amine groups with 0 to 20 carbon atoms. , Aryl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxyl group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and a combination thereof.

In this embodiment, when at least one of _{X 1 to} X ₈ and Y _{1 to Y 6} is selected from _{CR x} or CR _y , is at least one of _{X 1 to} X ₈ selected from _{CR x?} , Or at least one of _{Y 1 to Y 6 is selected from CR y} , and the R _x , R _y are selected from the non-hydrogen substituent group at the same or different for each appearance.

According to one embodiment of the 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 said. R _x and R _y are the same or different alkyl groups having 1 to 20 substituted or unsubstituted carbon atoms, and cycloalkyl groups having 3 to 20 substituted or unsubstituted ring carbon atoms, which are the same or different each time they appear. , 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, substituted or unsubstituted. Substituted aryloxy groups with 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups with 2 to 20 carbon atoms, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, substituted or unsubstituted carbon atoms Heteroaryl group number 3-30, substituted or unsubstituted alkylsilyl group with 3-20 carbon atoms, substituted or unsubstituted arylsilyl group with 6-20 carbon atoms, substituted or unsubstituted carbon atom 0 It is selected from the group consisting of an amine group, 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 a combination thereof.

In this _embodiment, the at least two or three of X 1 to X ₈ and _Y 1 to Y ₆ is selected from CR _x and / or CR _{y is} the X 1 to X ₈ and _Y 1 to Y ₆ Among them, at least one or more of the following situations are included. (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 is 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 , R _y is selected from the non-hydrogen substituent group, the same or different for each appearance.

（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 one embodiment of the present invention, the metal complex further comprises a ligand L _b having a structure represented by the following formula.

(R _{1 to} R ₇ are the same or different at each appearance of hydrogen, dehydrogen, halogen, an alkyl group having 1 to 20 substituted or unsubstituted carbon atoms, and 3 to 20 substituted or unsubstituted ring carbon atoms. Cycloalkyl groups, substituted or unsubstituted heteroalkyl groups with 1 to 20 carbon atoms, substituted or unsubstituted aralkyl groups with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups with 1 to 20 carbon atoms, Substituent or unsubstituted aryloxy group with 6 to 30 carbon atoms, substituted or unsubstituted alkenyl group with 2 to 20 carbon atoms, substituted or unsubstituted aryl group with 6 to 30 carbon atoms, substituted or unsubstituted Heteroaryl group with 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group with 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group with 6 to 20 carbon atoms, substituted or unsubstituted carbon From a group consisting of an amine group having 0 to 20 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 a combination thereof. Chosen,
Preferably, _{at least one or two of R 1 to} R ₃ are substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, and substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms. , substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms or selected from combinations thereof, and / or R ₄ at least one of to R ₆ is a substituted or unsubstituted carbon atoms 1, ~ 20 alkyl groups, substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, or a combination thereof.
More preferably, _{at least two of R 1 to} R ₃ are substituted or unsubstituted alkyl groups having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms, substituted. or unsubstituted heteroalkyl group having 2 to 20 carbon atoms or selected from combinations thereof, and / or R ₄ at least two of to R ₆ is substituted or unsubstituted 2 to 20 carbon atoms, Alkyl group, substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, 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 at each occurrence selected from _CR y1, _{CR y2} or N, and at least one of _Y 1 to Y ₆ one is selected from _{CR y2,} wherein _{R y2 has} the structure of a _{-L-SiR s1 R s2 R s3} ,
R _y1 , R _s1 , R _s2 , and R _s3 are the same or different at each appearance, such as hydrogen, heavy hydrogen, halogen, an alkyl group having 1 to 20 substituted or unsubstituted carbon atoms, and a substituted or unsubstituted ring carbon atom. Cycloalkyl group number 3 to 20, substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted carbon atom number 1 to 20 alkoxy groups, substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups with 2 to 20 carbon atoms, substituted or unsubstituted aryl groups with 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, substituted. Alternatively, 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 hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and these. Selected from a group of combinations,
L is a single-bonded, substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, or substituted or unsubstituted arylene having 6 to 20 carbon atoms. Selected from the group consisting of groups, substituted or unsubstituted heteroarylene groups having 3 to 20 carbon atoms, or combinations thereof.
Adjacent substituents R _s1 , R _s2 , and R _s3 may be bonded to form a ring.

In this embodiment, the adjoining substituents R _s1 , R _s2 , and R _s3 may be bonded to form a ring by substituting an adjacent substituent group, for example, the substituents R _s1 and R _{s2 with} each other. One or more of the adjacent substituent groups may be bonded to each other of the groups R _s1 and R _{s3 and the substituents R s2} and R _{s3 to form a ring.} Means. Obviously, none of these substituent groups need to be attached to form a ring.

According to one embodiment of the present invention, in the formula _1, Y 1 to Y ₆ are the same or different at each occurrence selected from _CR y1, _{CR y2} or N, and at least one of _Y 1 to Y ₆ One is _{selected from CR y1} , the R _y1 being fluorine.

According to one embodiment of the present invention, in the formula _1, at least one of Y 2 to Y ₆ is selected from _{CR y1,} wherein _{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, the metal in the metal complex, the relative atomic mass is selected from 40 than the metal, a metal complex containing a ligand L _a having the structure represented by the formula 1 'is disclosed To.

(Z is selected from O, S or Se,
X _{1 to} X ₈ are selected from _{C, CR x} or N, which are the same or different for each appearance.
Y ₁ to Y ₆ are the same or different at each occurrence selected from _CR y1, _{CR y2} or N, and at least one of _Y 1 to Y ₆ is selected from _{CR y2,} wherein _{R y2} is -L-SiR _s1 R _s2 R _s3 structure,
R _x , R _y1 , R _s1 , R _s2 , and R _s3 are the same or different at each appearance, hydrogen, dehydrogen, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted. Cycloalkyl group with 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl group with 1 to 20 carbon atoms, substituted or unsubstituted aralkyl group with 7 to 30 carbon atoms, substituted or unsubstituted carbon atom An alkoxy group having 1 to 20, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, an alkenyl group having 2 to 20 substituted or unsubstituted carbon atoms, and 6 to 30 substituted or unsubstituted carbon atoms. Aryl group, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms. Group, substituted or unsubstituted amine group with 0 to 20 carbon atoms, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxyl group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, And selected from the group consisting of these combinations,
L is a single-bonded, substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, or substituted or unsubstituted arylene having 6 to 20 carbon atoms. Selected from the group consisting of groups, substituted or unsubstituted heteroarylene groups having 3 to 20 carbon atoms, or combinations thereof.
Adjacent substituents R _x , R _s1 , R _s2 , and R _s3 may be combined 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, that is, an adjacent substituent group, for example, two substituents R _{x to} each other. , Substituents R _s1 and R _{s2 to} each other, Substituents R _s1 and R _{s3 to} each other, and Substituents R _s2 and R _{s3 to} each other, one or more of their adjacent substituent groups. It means that a ring may be formed. Obviously, those substituent groups do not have to bind to form a ring. Any of the adjacent substituents R _y1 may not be bonded to form a ring.

According to one embodiment of the present invention, the formula 1 or formula 1 ', two adjacent groups out of X ₁ to X ₄ is C, and one of the C carbon - the metal of a metal bond bind _to, the carbon of X 1 to X ₄ - one which is adjacent to the metal binding is selected from CR _x, wherein _{R x} is deuterium, halogen, substituted or unsubstituted carbon atoms 1 20 alkyl groups, substituted or unsubstituted cycloalkyl groups with 3 to 20 carbon atoms, substituted or unsubstituted heteroalkyl groups with 1 to 20 carbon atoms, substituted or unsubstituted carbon atoms with 7 to 30 Alkyl groups, substituted or unsubstituted alkoxy groups with 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups with 2 to 20 carbon atoms, substituted Or an unsubstituted 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, substituted or unsubstituted. Arylsilyl group having 6 to 20 carbon atoms, an amine group having 0 to 20 carbon atoms substituted or unsubstituted, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, and a 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 two of X 1 to} X ₄ are C, and one said C is bonded to the metal by a carbon-metal bond, and at that time, of X _{1 to} X ₄ . The one adjacent to the carbon-metal bond is _{selected from CR x} and the R _x is selected from the substituent group. For example, when X ₁ is C and X ₂ is also C to form a carbon-metal bond with a metal, _La is

Has the structure of. At that time, _{one of X 1 to} X ₄ adjacent to the carbon-metal bond refers to _{X 3.} X ₃ is _{selected from CR x} and the R _x is selected from the substituent group. However, for example, in the above formula 1, when X ₂ is C and X ₁ is also C to form a carbon-metal bond with a metal, the _La is

Has the structure of, among X ₁ to X _4, substitutable the carbon - absent adjacent position of the metal binding, clearly not context included in this embodiment.

According to one embodiment of the present invention, in the above 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 the _R x, R _y1 is the same or different at each appearance of heavy hydrogen, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, substituted or non-substituted. Substituted heteroalkyl groups with 1 to 20 carbon atoms, substituted or unsubstituted aralkyl groups with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups with 1 to 20 carbon atoms, substituted or unsubstituted carbon atoms Aryloxy groups of 6 to 30, substituted or unsubstituted alkenyl groups with 2 to 20 carbon atoms, substituted or unsubstituted aryl groups of 6 to 30 carbon atoms, substituted or unsubstituted carbon atoms of 3 to 30 Heteroaryl groups, substituted or unsubstituted alkylsilyl groups with 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups with 6 to 20 carbon atoms, substituted or unsubstituted amines with 0 to 20 carbon atoms. It is selected from the group consisting of a group, 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 a combination thereof.

In this embodiment, when _{at least one of X 1 to} X ₈ and Y _{1 to Y 6} is selected from _{CR x} or CR _y 1, is at least one of _{X 1 to} X ₈ selected from CR _x? Or, it means that at least one of _{Y 1 to Y 6 is selected from CR y} 1, and the R _x , R _{y 1} are selected from the non-hydrogen substituent group at the same or different each time they appear.

According to one embodiment of the present invention, in the above formula 1 _', at least two or three of X 1 to X ₈ and _Y 1 to Y ₆ is selected from CR _x or _{CR y1,} and the R _x , R _y1 are the same or different alkyl groups having 1 to 20 substituted or unsubstituted carbon atoms, and cycloalkyl groups having 3 to 20 substituted or unsubstituted ring carbon atoms, which are the same or different each time they appear. Substituted or unsubstituted heteroalkyl groups with 1 to 20 carbon atoms, substituted or unsubstituted aralkyl groups with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups with 1 to 20 carbon atoms, substituted or unsubstituted. Aryloxy groups with 6 to 30 carbon atoms, alkenyl groups with 2 to 20 substituted or unsubstituted carbon atoms, aryl groups with 6 to 30 substituted or unsubstituted carbon atoms, substituted or unsubstituted carbon atoms. 3 to 30 heteroaryl groups, substituted or unsubstituted alkylsilyl groups with 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups with 6 to 20 carbon atoms, substituted or unsubstituted carbon atoms 0 to 0 It is selected from the group consisting of 20 amine groups, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof.

In this _embodiment, the at least two or three of X 1 to X ₈ and _Y 1 to Y ₆ is selected from CR _x and / or _{CR y1 is} the X 1 to X ₈ and _Y 1 to Y ₆ Among them, at least one or more of the following situations are included. (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 y 1.} (4) At least one of _{X 1 to} X ₈ is selected from _{CR x} , and at least two of _{Y 1 to Y 6} are selected from _{CR y 1.} (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 y 1.} In any one of the above-mentioned situations, the _Rx and _Ry1 are selected from the non-hydrogen substituent group, the same or different for each appearance.

According to one embodiment of the present invention, in the formula 1 or formula 1', X ₇ is _{selected from CR x} or N, and R _x is hydrogen, dehydrogen, substituted or unsubstituted carbon atoms 1 to 1. 20 alkyl groups, substituted or unsubstituted cycloalkyl groups with 3 to 20 carbon atoms, substituted or unsubstituted heteroalkyl groups with 1 to 20 carbon atoms, substituted or unsubstituted carbon atoms 7 to 30 Aralkyl group, substituted or unsubstituted alkoxy group with 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group with 6 to 30 carbon atoms, substituted or unsubstituted alkenyl group with 2 to 20 carbon atoms, substituted Or an unsubstituted 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 group. Arylsilyl group having 6 to 20 carbon atoms, an amine group having 0 to 20 carbon atoms substituted or unsubstituted, an acyl group, a carbonyl group, a carboxyl group, an ester group, a cyano group, an isocyano group, a hydroxyl group, and a sulfanyl group. , Sulfinyl group, sulfonyl group, phosphino group, and a combination 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, the L _a has a structure represented by formula 2.

(Z is selected from O, S or Se,
X _{3 to} X _{8 are selected from CR x} or N, which are the same or different for each appearance.
Y ₁ to Y ₆ are the same or different at each occurrence selected from _CR y1, _{CR y2} or N, and at least one of _Y 1 to Y ₆ is selected from _{CR y2,} wherein _{R y2} is -L-SiR _s1 R _s2 R _s3 structure,
R _x , R _y1 , R _s1 , R _s2 , and R _s3 are the same or different at each appearance, hydrogen, dehydrogen, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted. Cycloalkyl group with 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl group with 1 to 20 carbon atoms, substituted or unsubstituted aralkyl group with 7 to 30 carbon atoms, substituted or unsubstituted carbon atom An alkoxy group having 1 to 20, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, an alkenyl group having 2 to 20 substituted or unsubstituted carbon atoms, and 6 to 30 substituted or unsubstituted carbon atoms. Aryl group, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms. Group, substituted or unsubstituted amine group with 0 to 20 carbon atoms, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxyl group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, And selected from the group consisting of these combinations,
L is a single-bonded, substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, or substituted or unsubstituted arylene having 6 to 20 carbon atoms. Selected from the group consisting of groups, substituted or unsubstituted heteroarylene groups having 3 to 20 carbon atoms, or combinations thereof.
Adjacent substituents R _x , R _s1 , R _s2 , and R _s3 may be combined to form a ring. )

According to one embodiment of the present _invention, Y 1 to Y ₂ is selected from the same or different and _{CR y1} or N on each _occurrence, Y 3 to Y ₆ are the same or different at each occurrence _CR y1, CR selected from _y2 or N, and at least one of _Y 3 to Y ₆ is selected from _{CR y2,} wherein _{R y2 has} the structure of a _{-L-SiR s1 R s2 R s3} ,
_Ry1 is the same or different at each appearance of hydrogen, dehydrogen, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, Substituted or unsubstituted heteroalkyl group with 1 to 20 carbon atoms, substituted or unsubstituted aralkyl group with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy group with 1 to 20 carbon atoms, substituted or unsubstituted Aryloxy group having 6 to 30 carbon atoms, an alkenyl group having 2 to 20 substituted or unsubstituted carbon atoms, an aryl group having 6 to 30 substituted or unsubstituted carbon atoms, and a substituted or unsubstituted carbon atom number. 3 to 30 heteroaryl groups, substituted or unsubstituted amine groups with 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, sulfanyl groups, sulfinyl groups, Selected from the group consisting of sulfonyl groups, phosphino groups, and combinations thereof,
R _s1 , R _s2 , and R _s3 are the same or different each time they appear, and each of them is hydrogen, dehydrogen, halogen, an alkyl group having 1 to 20 substituted or unsubstituted carbon atoms, and 3 to 3 substituted or unsubstituted ring carbon atoms. 20 cycloalkyl groups, substituted or unsubstituted heteroalkyl groups with 1 to 20 carbon atoms, substituted or unsubstituted aralkyl groups with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy with 1 to 20 carbon atoms Group, substituted or unsubstituted aryloxy group with 6 to 30 carbon atoms, substituted or unsubstituted alkenyl group with 2 to 20 carbon atoms, substituted or unsubstituted aryl group with 6 to 30 carbon atoms, substituted or Unsubstituted heteroaryl group with 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group with 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group with 6 to 20 carbon atoms, substituted or unsubstituted Consists of an amine group, 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 a combination thereof. Selected from the group,
L is a single-bonded, substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, or substituted or unsubstituted arylene having 6 to 20 carbon atoms. Selected from the group consisting of groups, substituted or unsubstituted heteroarylene groups having 3 to 20 carbon atoms, or combinations thereof.
Adjacent substituents R _s1 , R _s2 , and R _s3 may be bonded to form a ring.

In the present specification, adjacent substituents R _s1 , R _s2 , and R _s3 may be bonded to form a ring by substituting an adjacent substituent group, for example, substituents R _s1 and R _{s2 with} each other. One or more of the adjacent substituent groups may be bonded to each other of the groups R _s1 and R _{s3 and the substituents R s2} and R _{s3 to form a ring.} Means. Obviously, those substituent groups do not have to bind to form a ring. Any of the 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 _{selected from CR y1} or N, which _{are the same or different for each appearance, and R y1} is the same or different for each appearance, hydrogen, dehydrogen, halogen, and so on. Substituent or unsubstituted alkyl group with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group with 3 to 20 carbon atoms, substituted or unsubstituted heteroalkyl group with 1 to 20 carbon atoms, substituted or Unsubstituted aralkyl groups with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups with 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms, substituted or unsubstituted carbon Alkenyl groups with 2 to 20 atoms, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms, substituted or unsubstituted carbon atoms 0 to 0 It is selected from the group consisting of 20 amine groups, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof. The R _y1 is 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 hetero. It is indicated that an aryl 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 are selected. Alkyl group, cycloalkyl group, heteroalkyl group, aralkyl group, alkoxy group, aryloxy group, alkenyl group, aryl group, heteroaryl group, amino group, acyl group, carbonyl group, carboxyl group, ester group, sulfinyl group, sulfonyl group Any one of the group and the phosphino group is heavy hydrogen, halogen, an unsubstituted alkyl group having 1 to 20 carbon atoms, an unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, and an unsubstituted carbon. Heteroalkyl groups with 1 to 20 atoms, aralkyl groups with unsubstituted carbon atoms of 7 to 30, alkoxy groups with unsubstituted carbon atoms of 1 to 20, aryloxy groups with unsubstituted carbon atoms of 6 to 30, 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, and a hetero having an unsubstituted carbon atom number of 3 to 30. From aryl groups, unsubstituted amino groups with 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, phosphino groups and combinations thereof. It means that it may be replaced with one or more selected ones.

According to one embodiment of the present invention, R _s1 , R _s2 , and R _s3 are the same or different at each appearance, hydrogen, dehydrogen, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted. Or an unsubstituted or unsubstituted cycloalkyl group having 3 to 20 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 group. Substituted alkoxy group with 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group with 6 to 30 carbon atoms, substituted or unsubstituted alkenyl group with 2 to 20 carbon atoms, substituted or unsubstituted carbon atom An aryl group having 6 to 30, a heteroaryl group having 3 to 30 substituted or unsubstituted carbon atoms, an alkylsilyl group having 3 to 20 substituted or unsubstituted carbon atoms, and 6 to 6 substituted or unsubstituted carbon atoms. 20 arylsilyl groups, substituted or unsubstituted amine groups with 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.
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 is selected from the same or different and _{CR y1} or N on each _occurrence, Y 3 to Y ₆ are the same or different at each occurrence _CR y1, CR selected from _y2 or N, and at least one of _Y 3 to Y ₆ are selected from _{CR y2,} wherein _{R y2 has} the structure of a _{-L-SiR s1 R s2 R s3} ,
_Ry1 is the same or different at each appearance of hydrogen, dehydrogen, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, Substituted or unsubstituted heteroalkyl group with 1 to 20 carbon atoms, substituted or unsubstituted aralkyl group with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy group with 1 to 20 carbon atoms, substituted or unsubstituted Aryloxy group having 6 to 30 carbon atoms, an alkenyl group having 2 to 20 substituted or unsubstituted carbon atoms, an aryl group having 6 to 30 substituted or unsubstituted carbon atoms, and a substituted or unsubstituted carbon atom number. 3 to 30 heteroaryl groups, substituted or unsubstituted amine groups with 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, sulfanyl groups, sulfinyl groups, Selected from the group consisting of sulfonyl groups, phosphino groups, and combinations thereof,
R _s1 , R _s2 , and R _s3 are the same or differently substituted or substituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, and substitutions at each appearance. Or an unsubstituted 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, substituted or unsubstituted. Aryloxy groups with 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups with 2 to 20 carbon atoms, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, substituted or unsubstituted carbon atoms 3 Selected from the group consisting of ~ 30 heteroaryl groups, and combinations thereof,
L is a single-bonded, substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, or substituted or unsubstituted arylene having 6 to 20 carbon atoms. Selected from the group consisting of groups, substituted or unsubstituted heteroarylene groups having 3 to 20 carbon atoms, or combinations 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 the 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 ligand, the second ligand and the third ligand of the complex, respectively, m is selected from 1, 2 or 3, and n is 0. Selected from 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, if m is greater than 1, the plurality of _{L a,} the same or different, when n is 2, two _{L b} are the same or different, q is 2 If the two _Lc are the same or different,
L _{a, L b} and _{L c,} which may be bonded to form a multidentate ligand, for _example, L a, _L any two of _b and _{L c} are tetradentate binding to may form a ligand, also, for example, L _a, L _b and L _c may be joined to form a 6 tetradentate ligand with one another,
L _b and L _c are selected from the group consisting of the following structures, which are the same or different for each appearance.

R _a , R _b and R _c represent one-substitution, multiple-substitution, or no-substitution, which are the same or different for each appearance.
X _b is selected O on each occurrence identical or different, S, Se, from the group consisting of _{NR N1} and _CR C1 _{R C2,}
X _c and X _d are selected from the group consisting of _{O, S, Se and NR N2} , which are the same or different for each appearance.
R _a , R _b , R _c , _RN1 , _RN2 , _RC1 and _RC2 are the same or different alkyl groups with 1 to 20 carbon atoms of hydrogen, dehydrogen, halogen, substituted or unsubstituted at each appearance. , Substitutable or unsubstituted cycloalkyl group with 3 to 20 carbon atoms, substituted or unsubstituted heteroalkyl group with 1 to 20 carbon atoms, substituted or unsubstituted aralkyl group with 7 to 30 carbon atoms, substituted Alternatively, an unsubstituted 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 alkenyl group. An aryl group having 6 to 30 carbon atoms, a heteroaryl group having 3 to 30 substituted or unsubstituted carbon atoms, an alkylsilyl group having 3 to 20 substituted or unsubstituted carbon atoms, and a substituted or unsubstituted carbon atom number. 6 to 20 arylsilyl groups, substituted or unsubstituted amine groups with 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, sulfanyl groups, sulfinyl groups, Selected from the group consisting of sulfonyl groups, phosphino groups, and combinations thereof,
Adjacent substituents R _a , R _b , R _c , _RN1 , _RN2 , _RC1 and _RC2 may be combined to form a ring.

In this embodiment, the adjacent substituents R _a , R _b , R _c , _RN1 , _RN2 , _RC1 and _RC2 may be bonded to form a ring, that is, the adjacent substituent group. 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 to} each other, substituents R _a and RN _{1 to} each other, substituents R _b and RN _{1 to} each other, substituents R _a and RC _{1 to} each other, substituents R _a and RC _{2 to} each other, substituents R _b and RC _{1 to} each other, and substituents to each other. One or more of the substituent groups for R _b and RC _{2 to} each other, to the substituents R _a and RN _{2 to} each other, to each of the substituents R _b and RN ₂ , and to _{each other to R C 1} and RC _2. Means that they may combine to form a ring. Obviously, these substituents do not have to bond to each other 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 the 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 the first ligand, the second ligand and the third ligand of the complex, respectively, m is selected from 1, 2 or 3, and n is 0. Selected from 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, if m is greater than 1, the plurality of L _a, which may be the same or different, when n is 2, the two L _b, identical or different Again good, and q is 2, the two L _c may be the same or different, L _a, L _b and L _c, which may be bonded to form a multidentate ligand,
L _b is selected from the following structures, which are the same or different for each appearance.

X _c and X _d are selected from the group consisting of _{O, S, Se and NR N2} , which are the same or different for each appearance.
R _a1 , R _b1 , R _c1 , and _RN2 are the same or different each time they appear, such as hydrogen, dehydride, halogen, an alkyl group having 1 to 20 substituted or unsubstituted carbon atoms, and a substituted or unsubstituted ring carbon atom. Cycloalkyl group number 3 to 20, substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted carbon atom number 1 to 20 alkoxy groups, substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups with 2 to 20 carbon atoms, substituted or unsubstituted aryl groups with 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, substituted. Alternatively, 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 hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and these. Selected from a group of combinations,
Adjacent substituents R _a1 , R _b1 and R _c1 may be bonded to form a ring.
L _c is selected from the group consisting of the following structures, which are the same or different for each appearance.

R _a , R _b , and R _c represent one-substitution, multiple substitution, or no substitution, which are the same or different for each appearance.
X _e is selected from the group consisting of _{O, S, Se and NR N3} , which is the same or different for each appearance.
R _a , R _b , R _c , and _{RN 3} are the same or different at each appearance, such as hydrogen, dehydride, halogen, an alkyl group having 1 to 20 substituted or unsubstituted carbon atoms, and a substituted or unsubstituted ring carbon atom. Cycloalkyl group number 3 to 20, substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted carbon atom number 1 to 20 alkoxy groups, substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups with 2 to 20 carbon atoms, substituted or unsubstituted aryl groups with 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, substituted. Alternatively, 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 hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and these. Selected from a group of combinations,
Adjacent substituents R _b and R _c may be bonded to form a ring.

In this embodiment, the adjacent substituents R _a1 , R _b1 , and R _c1 may be bonded to each other to form a ring, that is, the substituents R _a1 and R _c1 or the substituents R _b1 and R _c1 are used with each other. It means that they may be combined 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 each other to form a ring.

In this embodiment, adjacent substituents R _b and R _c may be bonded to form a ring, which means that when a plurality of substituents R _b and a plurality of substituents R _c are present, they are adjacent to each other. It means that the substituents R _{b and} adjacent substituents R _c may be bonded to each other to form a ring. Obviously, when a plurality of substituents R _b and a plurality of substituents R _c are present, the adjacent substituents R _b or the adjacent substituents R _c do not need to be bonded to each other to form a ring. good.

According to one embodiment of the 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 the formula 3.

(M is 1 or 2 and
Z is selected from O or S, which is the same or different for each appearance.
X _{3 to} X _{8 are selected from CR x} or N, which are the same or different for each appearance.
Y _{1 to Y 6} are selected from _{CR y1} , CR _{y 2} or N differently for each appearance, and at least one of _{Y 1 to Y 6 is selected from CR y 2} , where R _{y 2} is −. It has a structure of L-SiR _s1 R _s2 R _s3 and has a structure of 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 the same or different for each appearance. , Substituent or unsubstituted alkyl group with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group with 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl group with 1 to 20 carbon atoms, substituted Or an unsubstituted 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, substituted or unsubstituted. An alkenyl group having 2 to 20 carbon atoms, an aryl group having 6 to 30 substituted or unsubstituted carbon atoms, a heteroaryl group having 3 to 30 substituted or unsubstituted carbon atoms, and 3 substituted or unsubstituted carbon atoms. Up to 20 alkylsilyl groups, substituted or unsubstituted arylsilyl groups with 6 to 20 carbon atoms, substituted or unsubstituted amine groups with 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxyl groups, ester groups, Selected from the group consisting of a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and a combination thereof.
L is a single-bonded, substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, or substituted or unsubstituted arylene having 6 to 20 carbon atoms. Selected from the group consisting of groups, substituted or unsubstituted heteroarylene groups having 3 to 20 carbon atoms, or combinations thereof.
Adjacent substituents R _x , R _s1 , R _s2 , and R _s3 may be combined to form a ring.
Adjacent substituents R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ and R ₇ may be combined to form a ring. )

In this embodiment, adjacent substituents R _x , R _s1 , R _s2 , and R _s3 may be bonded to form a ring, that is, an adjacent substituent group, for example, two substituents R _{x to} each other. , Substituents R _s1 and R _{s2 to} each other, Substituents R _s1 and R _{s3 to} each other, and Substituents R _s2 and R _{s3 to} each other, any one or more of the substituent groups bonded to each other. It means that a ring may be formed. Obviously, those substituent groups do not have to bind to form a ring.

In this embodiment, the may form a ring substituent adjacent _{R 1, R 2, R 3} , R 4, R 5, R 6, R 7 are binding, adjacent substituent groups, For example, substituents _{R 1} and _{R 2} together, with each other substituents _{R 1} and _{R 3,} together substituents _{R 2} and _{R 3,} substituents _{R 4} and _{R 5} together, the substituents _{R 5} and _{R 6} together, the substituents R ₄ and _{R 6} to each other, between the substituents _{R 1} and _{R 7,} together substituents _{R 2} and _{R 7,} the substituents _{R 3} and _{R 7} together, the substituents _{R 4} and _{R 7} together, the substituents _{R 5} and _{R 7} together , And one or more of the substituent groups may be attached to each of the _{substituents R 6} and R _{7 to form a ring.} Obviously, those substituent groups do not have to bind 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 the formula 3.

(M is 1 or 2 and
Z is selected from O or S, which is the same or different for each appearance.
R _{1 to} R ₇ are the same or different each time they appear, such as hydrogen, dehydrogen, halogen, an alkyl group having 1 to 20 substituted or unsubstituted carbon atoms, and a cyclo having 3 to 20 substituted or unsubstituted ring carbon atoms. Alkyl group, substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted Or an unsubstituted 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, substituted or unsubstituted. Heteroaryl group with 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group with 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group with 6 to 20 carbon atoms, substituted or unsubstituted carbon atom Select from the group consisting of an amine group, 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 a combination thereof. Is done. )

（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 the formula 3.

(M is 1 or 2 and
Z is selected from O or S, which is the same or different for each appearance.
At _{least one of R 1 to} R ₃ is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted. heteroalkyl group having 1 to 20 carbon atoms or at least one is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms of selected from these combinations, and / or R ₄ to R _6,, A substituted or unsubstituted cycloalkyl group having 3 to 20 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 the formula 3.

(M is 1 or 2 and
Z is selected from O or S, which is the same or different for each appearance.
At _{least two of R 1 to} R ₃ are substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted. heteroalkyl group having 1 to 20 carbon atoms or at least one is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms of selected from these combinations, and / or R ₄ to R _6,, A substituted or unsubstituted cycloalkyl group having 3 to 20 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 the formula 3.

(M is 1 or 2 and
Z is selected from O or S, which is the same or different for each appearance.
At _{least two of R 1 to} R ₃ are substituted or unsubstituted alkyl groups having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted. heteroalkyl group having 2 to 20 carbon atoms or selected from combinations thereof, and / or at least two of R ₄ to R ₆ is a substituted or unsubstituted alkyl group having 2 to 20 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 20 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 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 formulas 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 is selected from CR _x independently.

According to one embodiment of the present invention, in formulas 2 and / or formula 3, X _{3 to} X ₈ are independently _{selected from CR x} , and the R _x is hydrogen, dehydrogen, halogen, or substituted. Or an unsubstituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or non-substituted ring. It is selected from an arylsilyl group having 6 to 20 carbon atoms, a cyano group, or a combination thereof.

According to one embodiment of the present invention, in formulas 2 and / or formula 3, X _{3 to} X ₈ are independently _{selected from CR x} , and the R _x is a hydrogen, dehydrogen, fluorine, or methyl group. , Ethyl group, isopropyl group, isobutyl group, tert-butyl group, neopentyl group, cyclopentyl group, cyclopentylmethyl group, cyclohexyl group, norbol group, adamantyl group, trimethylsilyl group, isopropyldimethylsilyl group, phenyldimethylsilyl group, trifluoromethyl It is selected from the group consisting of groups, cyano groups, and combinations thereof.

According to one embodiment of the present invention, in formulas 2 and / or formula 3, X ₃ is CR _x , and the R _x is hydrogen, dehydrogen, halogen, substituted or unsubstituted carbon atoms 1 to 20. Alkyl group, substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms. It is selected from a silyl group, a cyano group, or a combination thereof.

According to one embodiment of the present invention, in formulas 2 and / or formula 3, X ₃ is _{selected from CR x} , and the R _x is deuterium, halogen, substituted or unsubstituted carbon atoms 1 to 1. It is selected from 20 alkyl groups, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, cyano groups, or combinations thereof.

According to one embodiment of the invention, in Formulas 2 and / or Formula 3, X ₃ is _{selected from CR x} and said R _x is selected from a methyl group or a deuterated methyl group.

According to one embodiment of the invention, Y ₂ is _{selected from CR y1} or CR _y2 , wherein the R _y1 is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted ring carbon. Selected from the group consisting of cycloalkyl groups having 3 to 20 atoms and combinations thereof, the R _y2 has a structure of −L—SiR _s1 R _s2 R _{s3 , and R s1} , R _s2 and R _s3 are , Same or different hydrogen, dehydrogen, halogen, substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group with 3 to 20 ring carbon atoms, substituted or non-substituted with each appearance. Substituted heteroalkyl groups with 1 to 20 carbon atoms, substituted or unsubstituted aralkyl groups with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups with 1 to 20 carbon atoms, substituted or unsubstituted carbon atoms 6 to 30 aryloxy groups, substituted or unsubstituted alkenyl groups with 2 to 20 carbon atoms, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, substituted or unsubstituted carbon atoms 3 to 30 Heteroaryl group, substituted or unsubstituted alkylsilyl group with 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group with 6 to 20 carbon atoms, substituted or unsubstituted amine with 0 to 20 carbon atoms. Selected from the group consisting of a group, 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 a combination thereof, L is a simple substance. Bonded, substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, substituted or unsubstituted arylene group having 6 to 20 carbon atoms, substituted or Selected from the group consisting of an 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} is, _-L-SiR s1 _{R s2 R It} has a structure of s3, L is selected from a single bond, and R _s1 , R _s2 and R _s3 are independently substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted, respectively. It is selected from the group consisting of cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted 6 to 20 aryl groups having carbon atoms, and combinations thereof.

According to one embodiment of the present invention, in formulas 2 and / or formula 3, Y ₂ and / or Y ₄ are _{selected from CR y2} , and R _y2 has a structure of −L—SiR _s1 R _s2 R _s3. Has L is selected from a single bond, R _s1 , R _s2 and R _s3 are independently substituted or unsubstituted alkyl groups with 1 to 20 carbon atoms, substituted or unsubstituted ring carbon atoms, respectively. cycloalkyl group having 3 to 20, a substituted or unsubstituted carbon atoms 6 to 20 aryl group, and is selected from the group consisting of, _and, at least one of R _{s1, R s2} and _{R s3} or Two or three are independently selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 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} is, _-L-SiR s1 _{R s2 R It} has a structure of s3, L is selected from a single bond, and R _s1 , R _s2 and R _s3 are independently methyl group, ethyl group, isopropyl group, isobutyl group, tert-butyl group, neopentyl group, respectively. It is selected from the group consisting of a cyclopentyl group, a cyclopentylmethyl group, a cyclohexyl group, a norbol group, an adamantyl group, a trifluoromethyl group, a phenyl group, and a combination thereof.

According to one embodiment of the present invention, in the above formula 1 (or 1 _'), Y 1 to Y ₆ is selected from the same or different at each occurrence CR _y (or _{CR y1)} or _{N, R} y ( _{Alternatively,} R y1) is the same or different for each appearance of hydrogen, dehydrogen, halogen, an alkyl group having 1 to 20 substituted or unsubstituted carbon atoms, and a substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms. Group, substituted or unsubstituted heteroalkyl group with 1 to 20 carbon atoms, substituted or unsubstituted aralkyl group with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy group with 1 to 20 carbon atoms, substituted or Unsubstituted aryloxy group with 6 to 30 carbon atoms, substituted or unsubstituted alkenyl group with 2 to 20 carbon atoms, substituted or unsubstituted aryl group with 6 to 30 carbon atoms, substituted or unsubstituted carbon Heteroaryl groups with 3 to 30 atoms, substituted or unsubstituted alkylsilyl groups with 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups with 6 to 20 carbon atoms, substituted or unsubstituted carbon atoms Selected from the group consisting of 0 to 20 amine groups, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof. And the R _y (or R _y1 ) is 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. When selected, the substituents are hydrogen, dehydride, halogen, an unsubstituted alkyl group having 1 to 20 carbon atoms, an unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, and an unsubstituted carbon atom number. 1 to 20 heteroalkyl groups, unsubstituted aralkyl groups with 7 to 30 carbon atoms, unsubstituted alkoxy groups with 1 to 20 carbon atoms, unsubstituted aryloxy groups with 6 to 30 carbon atoms, unsubstituted An alkenyl group having 2 to 20 carbon atoms, an aryl group having 6 to 30 unsubstituted carbon atoms, a heteroaryl group having 3 to 30 unsubstituted carbon atoms, and an alkylsilyl having 3 to 20 unsubstituted carbon atoms. A group, an arylsilyl group having 6 to 20 unsubstituted carbon atoms, an amine group having 0 to 20 unsubstituted carbon atoms, an acyl group, a carbonyl group, a carboxyl group, an ester group, a hydroxyl group, a sulfanyl group, a sulfinyl group, It is selected from the group consisting of a sulfonyl group, a phosphino group, and a combination thereof.

According to one embodiment of the present invention, in the formula 1 or 1', X _{1 to} X _{8 are selected from C, CR x} or N, which are the same or different for each appearance, and R _x is the same for each appearance. Or differently hydrogen, dehydrogen, halogen, substituted or unsubstituted alkyl groups with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups with 3 to 20 ring carbon atoms, substituted or unsubstituted carbon atoms. 1 to 20 heteroalkyl groups, substituted or unsubstituted aralkyl groups with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups with 1 to 20 carbon atoms, substituted or unsubstituted carbon atoms 6 to 30 Aryloxy groups, substituted or unsubstituted alkyl groups with 2 to 20 carbon atoms, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms, Substituent or unsubstituted alkylsilyl groups with 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups with 6 to 20 carbon atoms, substituted or unsubstituted amine groups with 0 to 20 carbon atoms, acyl groups, It is selected from the group consisting of 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 a combination thereof.

According to one embodiment of the present invention, _{L a} is any one selected from the group consisting of _L a1 _{~L a1539} same or different at each occurrence. The specific structure of the _L a1 _{~L a1539,} please refer to the 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, _{L a} is any one selected from the group consisting of _L a1 _{~L a1539} same or different at each occurrence.
for example,

During,
It represents that L _{a1 to} La ₁₂ are selected from the structures listed therein. With _{respect to La 1} , the substituent R ^a in the structure is H, and the structure of _{La 1 is}

Indicates that. Similarly, with _{respect to La 2} , the substituent R ^a in its structure is CH ₃ , and the structure of _{La 2 is}

Indicates that. In similar _manner, with respect to _{L a3,} substituents ^{R a} in the structure is ^{R a1, R a1} is

And the structure of _{La3 is}

Indicates that. Even for _{L a4} ~L a1507, it is the same.

According to one embodiment of the present invention, _{L a} is any one selected from the group consisting of _L a1 _{~L a1611} same or different at each occurrence. The specific structure of the _L a1 _{~L a1611,} please refer to the 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 are the same or different for each appearance.

,
(R _{1 to} R ₇ are independently hydrogen, deuterium, halogen, an alkyl group having 1 to 20 substituted or unsubstituted carbon atoms, and a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms. , Cyano groups, and combinations thereof.
Adjacent substituents R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ and R ₇ may be combined to form a ring. )

In this embodiment, the may form a ring substituent adjacent _{R 1, R 2, R 3} , R 4, R 5, R 6, R 7 are binding, adjacent substituent groups, For example, substituents _{R 1} and _{R 2} together, with each other substituents _{R 1} and _{R 3,} together substituents _{R 2} and _{R 3,} substituents _{R 4} and _{R 5} together, the substituents _{R 5} and _{R 6} together, the substituents R ₄ and _{R 6} to each other, between the substituents _{R 1} and _{R 7,} together substituents _{R 2} and _{R 7,} the substituents _{R 3} and _{R 7} together, the substituents _{R 4} and _{R 7} together, the substituents _{R 5} and _{R 7} together , And, to the substituents R ₆ and R ₇ , at least one or more of the substituent groups may be bonded to each other to form a ring. Obviously, those substituent groups do not have to bind to form a ring.

According to one embodiment of the present invention, R _{1 to} R ₇ are the same or different at each appearance, hydrogen, dehydro group, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted. Cycloalkyl group having 3 to 20 ring carbon atoms, heteroalkyl group having 1 to 20 substituted or unsubstituted carbon atoms, aralkyl group having 7 to 30 substituted or unsubstituted carbon atoms, substituted or unsubstituted carbon An alkoxy group having 1 to 20 atoms, an aryloxy group having 6 to 30 substituted or unsubstituted carbon atoms, an alkenyl group having 2 to 20 substituted or unsubstituted carbon atoms, and 6 to 20 substituted or unsubstituted carbon atoms. 30 aryl groups, substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups with 3 to 20 carbon atoms, substituted or unsubstituted aryls with 6 to 20 carbon atoms From a silyl group, 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 hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and a combination thereof. R _{1 to} R ₇ are independently substituted alkyl groups having 1 to 20 carbon atoms, substituted cycloalkyl groups having 3 to 20 ring carbon atoms, and substituted carbon atoms 1 When selected from ~ 20 heteroalkyl groups, substituted aryl groups with 6-30 carbon atoms or substituted heteroaryl groups with 3-30 carbon atoms, the substituents are hydrogen, dehydride, halogen, unsubstituted. Alkyl group having 1 to 20 carbon atoms, cycloalkyl group having 3 to 20 unsubstituted ring carbon atoms, heteroalkyl group having 1 to 20 unsubstituted carbon atoms, and 7 to 30 unsubstituted carbon atoms. Aralkyl group, unsubstituted alkoxy group with 1 to 20 carbon atoms, unsubstituted aryloxy group with 6 to 30 carbon atoms, unsubstituted alkenyl group with 2 to 20 carbon atoms, and unsubstituted carbon atom number 6 ~ 30 aryl groups, unsubstituted heteroaryl groups with 3 to 30 carbon atoms, unsubstituted alkylsilyl groups with 3 to 20 carbon atoms, unsubstituted arylsilyl groups with 6 to 20 carbon atoms, unsubstituted It is selected from the group consisting of an amine group having 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 a combination 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 are the same or different for each appearance.

(R _{1 to} R ₇ are independently hydrogen, dehydrogen, fluorine, methyl group, ethyl group, propyl group, isopropyl group, isobutyl group, n-butyl group, tert-butyl group, n-pentyl group and isopentyl. It is selected from the group consisting of a group, a neopentyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cyano group, and a combination thereof.)

According to one embodiment of the present invention, L _b is any one selected from the group consisting of _{L b1 to} L _b322, which is the same or different for each appearance. Please refer to claim 22 for the specific structure of L _{b1 to} L _b322.

According to one embodiment of the present invention, L _c is any one selected from the group consisting of _{L c1 to} L _c231, which is the same or different for each appearance. Please refer to claim 23 for the specific structure of L _{c1 to} L _c231.

According to one embodiment of the present invention, the metal complex, _Ir and _{(L a) 2 (L b} ) or _{Ir (L a) 2 (L} c) or _{Ir (L a) (L c} ) 2 of the structure Have.

Wherein if the metal complex is having the structure of _{Ir (L a) 2 (L} b), L a is 2 any one or any one selected from the group consisting of _L a1 _{~L a1539} same or different at each occurrence It is a species, and L _b is any one selected from the group consisting of _{L b1 to} L _b322. Wherein if the metal complex is having the structure of _{Ir (L a) 2 (L} c), L a is 2 any one or any one selected from the group consisting of _L a1 _{~L a1539} same or different at each occurrence It is a species, and L _c is any one selected from the group consisting of _{L c1 to} L _c231. If the metal complex has a _{Ir (L a) (L c} ) 2 of the structure, _{L a is} any one selected from the group consisting of _{L a1 ~L} a1539, L _c is the same on each occurrence Or differently, any one or two selected from the group consisting of _{L c1 to} L _c231.

According to one embodiment of the present invention, the metal complex, _Ir and _{(L a) 2 (L b} ) or _{Ir (L a) 2 (L} c) or _{Ir (L a) (L c} ) 2 of the structure Have.

Wherein if the metal complex is having the structure of _{Ir (L a) 2 (L} b), L a is 2 any one or any one selected from the group consisting of _L a1 _{~L a1611} same or different at each occurrence It is a species, and L _b is any one selected from the group consisting of _{L b1 to} L _b322. Wherein if the metal complex is having the structure of _{Ir (L a) 2 (L} c), L a is 2 any one or any one selected from the group consisting of _L a1 _{~L a1611} same or different at each occurrence It is a species, and L _c is any one selected from the group consisting of _{L c1 to} L _c231. If the metal complex has a _{Ir (L a) (L c} ) 2 of the structure, _{L a is} any one selected from the group consisting of _{L a1 ~L} a1611, L _c is the same on each occurrence Or differently, any one or two selected from the group consisting of _{L c1 to} L _c231.

According to one embodiment of the present invention, the metal complex is selected from the group consisting of compounds 1 to 300. Please refer to claim 24 for the specific structure of the compounds 1 to 300.

According to one embodiment of the present invention, the metal complex is selected from the group consisting of compounds 1 to 316. Please refer to claim 24 for the specific structure of the above compounds 1 to 316.

（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
With the anode
With the cathode
Further disclosed is an electroluminescent device comprising an organic layer provided between the anode and the cathode. The organic layer contains a metal complex, which has a maximum emission wavelength of 612 nm or more, preferably 615 nm or more in the photoluminescence spectrum (PL). Metal in the metal complex, the relative atomic mass is selected from 40 than the metal, containing a ligand L _a having the structure represented by Formula 1.

(Z is selected from O,
X _{1 to} X ₈ are selected from _{C, CR x} or N, which are the same or different for each appearance.
Y _{1 to Y 6 are selected from CR y} or N, which are the same or different for each appearance.
R _x and R _y are the same or different each time they appear, such as hydrogen, dehydrogen, halogen, an alkyl group having 1 to 20 substituted or unsubstituted carbon atoms, and a cyclo having 3 to 20 substituted or unsubstituted ring carbon atoms. Alkyl group, substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted Or an unsubstituted 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, substituted or unsubstituted. Heteroaryl group with 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group with 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group with 6 to 20 carbon atoms, substituted or unsubstituted carbon atom Select from the group consisting of an amine group, 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 a combination thereof. Re,
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
With the anode
With the cathode
Further disclosed is an electroluminescent device comprising an organic layer provided between the anode and the cathode. The organic layer contains the metal complex, the metal in the metal complex, the relative atomic mass is selected from 40 than the metal, containing a ligand L _a having the structure represented by the formula 1 '.

(Z is selected from O, S or Se,
X _{1 to} X ₈ are selected from _{C, CR x} or N, which are the same or different for each appearance.
Y ₁ to Y ₆ are the same or different at each occurrence selected from _CR y1, _{CR y2} or N, and at least one of _Y 1 to Y ₆ is selected from _{CR y2,} wherein _{R y2} is -L-SiR _s1 R _s2 R _s3 structure,
R _x , R _y1 , R _s1 , R _s2 , and R _s3 are the same or different at each appearance, hydrogen, dehydrogen, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted. Cycloalkyl group with 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl group with 1 to 20 carbon atoms, substituted or unsubstituted aralkyl group with 7 to 30 carbon atoms, substituted or unsubstituted carbon atom An alkoxy group having 1 to 20, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, an alkenyl group having 2 to 20 substituted or unsubstituted carbon atoms, and 6 to 30 substituted or unsubstituted carbon atoms. Aryl group, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms. Group, substituted or unsubstituted amine group with 0 to 20 carbon atoms, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxyl group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, And selected from the group consisting of these combinations,
L is a single-bonded, substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, or substituted or unsubstituted arylene having 6 to 20 carbon atoms. Selected from the group consisting of groups, substituted or unsubstituted heteroarylene groups having 3 to 20 carbon atoms, or combinations thereof.
Adjacent substituents R _x , R _s1 , R _s2 , and R _s3 may be combined 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 device emits red light.

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

According to an embodiment of the present invention, in the device, the organic layer is a light emitting layer, and the light 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 is benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazolyl, dibenzothiophene, azadibenzothiophene, dibenzofuran. , Azadibenzofuran, dibenzoselenovene, triphenylene, azatriphenylene, fluorenyl, siliconfluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxalin, phenanthrene, azaphenanthrene, and at least one chemical group selected from the group consisting of these. include.

According to other embodiments of the invention, formulations of compounds containing metal complexes are further disclosed. The specific structure of the metal complex is shown in any one of the examples described above.

Combination with other materials

The material of the specific layer used for the organic light emitting device described in the present invention can be used in combination with various other materials existing in the device. The combination of these materials is described in detail in paragraphs 0132 to 0161 of US patent application US2016 / 0359122A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned are non-limiting examples of materials that can be used in combination with the compounds disclosed herein and are available to those of skill in the art with reference to the literature in combination. Other materials can be identified.

In the present specification, it is described that the material of the specific layer used for the organic light emitting device can be used in combination with various other materials existing in the device. Illustratively, the luminescent dopants disclosed herein can be used in combination with a wide variety of hosts, transport layers, blocking layers, injection layers, electrodes and other possible layers. The combinations of these materials are described in detail in paragraphs 0080 to 0101 of patent application US2015 / 0349273A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned are non-limiting examples of materials that can be used in combination with the compounds disclosed herein and are available to those of skill in the art with reference to the literature in combination. Other materials can be identified.

In material synthesis examples, all reactions are carried out with nitrogen protection, unless otherwise stated. All reaction solvents are anhydrous and are used as they are from commercial products. For the product to be synthesized, one or more instruments commonly used in the art (Bruker nuclear magnetic resonance apparatus, Shimadzu liquid chromatography, liquid chromatography / mass spectrometer, gas chromatography / mass spectrometer). , Including but not limited to differential heat scanning calorimeter, Shanghai ▲ Ryo ▼ Phototechnology's fluorescence spectrophotometer, Wuhan Kazushi's special electrochemical work station, Anhui Ikatsu's sublimation device, etc.) , Structural confirmation and characteristic test were performed by a method familiar to those skilled in the art. In the example of the element, for the characteristics of the element, ordinary equipment in this field (a vapor deposition machine manufactured by Angstrom Engineering, an optical test system manufactured by Suzhou Fushida, a life test system, an ellipsometer manufactured by Beijing Quantum Taku, etc. Tests were performed in a manner familiar to those skilled in the art, including but not limited to). Since those skilled in the art know the related contents such as the use of the above-mentioned equipment and the test method, the specific data of the sample can be surely and unaffected, and the above-mentioned related contents are repeated in the present specification. I will not explain.

Examples of material synthesis:

The method for preparing the compound according to the present invention is not limited. Typical, but not limited to, the following compounds are taken as examples, and their synthetic routes and preparation methods are as follows.

Example of Synthesis 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. Then, after cooling the reaction solution to 0 ° C., NaH (10.6 g, 281.5 mmol) was added in several portions. After the addition was complete, the solution was continuously stirred at 0 ° C. until there was no apparent gas discharge in the solution. Then, methane iodide (46.7 g, 328.4 mmol) was added. The reaction was then heated to room temperature and stirred overnight. After the reaction was shown to be complete by TLC, water and ethyl acetate were added, extracted and combined with the organic phase. The organic phase was washed with saturated brine multiple times, dried, and rotated to completely remove the solvent by rotary evaporation to obtain a crude product. Separation by silica gel column chromatography (the eluent is petroleum ether) gave Intermediate 1 (57.7 g, 94.3%), which is a colorless oily liquid, as a target product.

Step 2: Synthesis of Intermediate 2

Intermediate 1 (31.7 g, 113.2 mmol) was dissolved in 230 mL of ultradry methyl tert-butyl ether (MTBE). Then, the reaction solution was cooled to −72 ° C. Next, an n-butyllithium solution (50 mL, 125 mmol) was added dropwise under the protection of nitrogen gas. After the dropping was completed, the temperature was continuously maintained for 30 minutes. Then, trimethyl borate (17.6 g, 169.8 mmol) was added. After the addition was completed, the reaction was heated to room temperature and reacted for 2 hours. Then, 250 mL of 2 m HCl was added, and the mixture was continuously stirred at room temperature for 2 hours. 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 merged. It was dried and rotated so as to completely remove the solvent by rotary evaporation to obtain a crude product as a yellow solid. Then, 150 mL of n-hexane was added, and the mixture was heated to reflux for 1 h. It is then cooled to room temperature, filtered, the solid collected, washed multiple times with hexane and then pumped for drying, Intermediate 2 (16.5 g, 59.7%), which is a white powder. ) Was obtained.

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, replaced with nitrogen gas and refluxed overnight. After the reaction completion was detected by TLC, the mixture was cooled to room temperature, diluted with water, extracted with dichloromethane, and combined with an organic phase. It is dried, rotary-evaporated, separated by silica gel column chromatography (eluting agent is ethyl acetate: petroleum ether = 1: 100, v / v), and is a colorless oily liquid Intermediate 3 (12.9 g, 58.3%) was obtained.

Step 4: Synthesis of Intermediate 4

Intermediate 3 (12.9 g, 39.4 mmol) was dissolved in 150 mL of dichloromethane. Then, after cooling the reaction solution to 0 ° C., boron tribromide (15.3 g, 61.1 mmol) was gradually added. Then, the reaction was continued at the temperature for 2 hours. After the reaction was shown to be complete by TLC, water was carefully added to quench the reaction, extracted with dichloromethane and combined with the organic phase. Dry, rotary evaporate, and separated by silica gel column chromatography (eluting agent is ethyl acetate: petroleum ether = 1: 50, v / v), intermediate 4 (10.9 g, 88) which is a white solid. .3%) was obtained.

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-necked flask, the resulting reaction mixture was protected by nitrogen gas. It was heated to 100 ° C. underneath and reacted overnight. After cooling the reaction mixture to room temperature, water and ethyl acetate were added, extracted and combined with the organic phase. The organic phase was washed with saturated brine multiple times, dried, and rotated to completely remove the solvent by rotary evaporation to obtain a crude product. Separation by silica gel column chromatography (the 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), respectively, in a 250 mL three-necked flask. After adding potassium acetate (5.2 g, 53.0 mmol) and 1,4-dioxane (100 mL), the resulting reaction mixture was heated to reflux under the protection of nitrogen gas and allowed to react overnight. After cooling the reaction mixture to room temperature, water and ethyl acetate were added, extracted and combined with the organic phase. The organic phase was washed with saturated brine multiple times, dried, and rotated to completely remove the solvent by rotary evaporation to obtain a crude product. Separated by silica gel column chromatography (eluting agent is ethyl acetate: petroleum ether = 1: 50, v / v), intermediate 6 (10.2 g, 85.4%) which is a white solid as a target product. ) Was obtained.

Step 7: Synthesis of Intermediate 7

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), respectively, in a 250 mL three-necked flask. After adding sodium carbonate (3.3 g, 31.1 mmol), 1,4-dioxane (80 mL) and water (20 mL), the resulting reaction mixture is heated to reflux under the protection of nitrogen gas overnight. It was reacted. The reaction mixture was cooled to room temperature and then filtered. The obtained solid was washed with water and petroleum ether multiple times in order and then dried to obtain a crude product. Separated by silica gel column chromatography (eluent is dichloromethane: petroleum ether = 1: 3 and v / v), intermediate 7 (5.7 g, 65.2%) which is a white solid as a target product). Got

Step 8: Synthesis of Intermediate 8

Intermediate 7 (5.2 g, 12.4 mmol) was dissolved in 250 mL of ultradry tetrahydrofuran and then the reaction solution was cooled to −72 ° C. Next, an n-butyllithium solution (5.5 mL, 13.6 mmol) was added dropwise under the protection of nitrogen gas. After the dropping was completed, the temperature was continuously maintained for 1 hour. Then, trimethylsilyltrifluoromethanesulfonate (TMSOTf) (3.3 g, 14.9 mmol) was added. After the addition was completed, the reaction was heated to room temperature and reacted for 2 hours. Then, a saturated sodium hydrogen carbonate solution was added to quench the reaction. Ethyl acetate was then added to the reaction and the solution was separated. The aqueous phase was extracted with ethyl acetate and combined with the organic phase. It was dried and rotated so as to completely remove the solvent by rotary evaporation to obtain a crude product. Separated by silica gel column chromatography (eluent is dichloromethane: petroleum ether = 1: 3 and v / v), intermediate 8 (3.2 g, 62.4%) which is a white solid as a target product). Got

Step 9: Synthesis of 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) sustained under nitrogen gas protection. Then, it was refluxed for 24 hours. After cooling to room temperature, the water in the solution was carefully spun off by rotary evaporation to give an iridium dimer of ethoxyethanol solution. It does not need to be further purified and can be used as it is for the next reaction.

Step 10: Synthesis of compound 77

Iridium dimer ethoxyethanol solution 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) was 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 put into a funnel filled with diatomaceous earth, filtered and washed with ethanol. Dichloromethane was added to the obtained solid and the filtrate was collected. Then ethanol is added to concentrate the resulting solution, but not until it is complete. After filtration, 0.52 g of the 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 a target product with a molecular weight of 1282.4.

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). In a 1 L reaction flask, 300 mL of toluene, 100 mL of ethanol and 100 mL of water were added. Vacuum the system, replace with nitrogen gas, and reflux overnight. After the reaction completion was detected by TLC, the mixture was cooled to room temperature, diluted with water, extracted with dichloromethane, and combined with an organic phase. Dry, rotary evaporate, and separated by silica gel column chromatography (eluting agent is ethyl acetate: petroleum ether = 1: 100, v / v), intermediate 9 (39 g, 64.) Which is a colorless oily liquid. 1%) was obtained.

Step 2: Synthesis of Intermediate 10

Intermediate 9 (39 g, 132.1 mmol) was dissolved in 500 mL of dichloromethane. Then, after cooling the reaction solution to 0 ° C., boron tribromide (49.7 g, 198.2 mmol) was gradually added, and the reaction was continued at the temperature for 2 hours. After the reaction was shown to be complete by TLC, water was carefully added to quench the reaction, extracted with dichloromethane and combined with the organic phase. Dry, rotary evaporate, and separated by silica gel column chromatography (eluting agent is ethyl acetate: petroleum ether = 1: 50, v / v), intermediate 10 (31.8 g, 85) which is a white solid. .5%) was obtained.

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-necked flask, respectively. Then, the obtained reaction mixture was heated at 100 ° C. under the protection of nitrogen gas and reacted overnight. After cooling the reaction mixture to room temperature, water and ethyl acetate were added, extracted and combined with the organic phase. The organic phase was washed with saturated brine multiple times, dried, and rotated to completely remove the solvent by rotary evaporation to obtain a crude product. Separation by silica gel column chromatography (the 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

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), respectively, in a 250 mL three-necked flask. 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 allowed to react overnight. After cooling the reaction mixture to room temperature, water and ethyl acetate were added, extracted and combined with the organic phase. The organic phase was washed with saturated brine multiple times, dried, and rotated to completely remove the solvent by rotary evaporation to obtain a crude product. Separated by silica gel column chromatography (eluting agent is ethyl acetate: petroleum ether = 1: 50, v / v), intermediate 12 (13.5 g, 69.8%) which is a white solid as a target product. ) Was obtained.

Step 5: Synthesis of Intermediate 13

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), respectively, in a 250 mL three-necked flask. After adding sodium carbonate (3.4 g, 32.1 mmol), 1,4-dioxane (90 mL) and water (20 mL), the resulting reaction mixture is heated to reflux under the protection of nitrogen gas overnight. It was reacted. The reaction mixture was cooled to room temperature and then filtered. The obtained solid was washed with water and petroleum ether multiple times in order and then dried to obtain a crude product. Separated by silica gel column chromatography (eluent is dichloromethane: petroleum ether = 1: 3 and v / v), intermediate 13 (5.2 g, 62.6%) which is a white solid as a target product. Got

Step 6: Synthesis of Intermediate 14

Intermediate 13 (5.2 g, 13.4 mmol) was dissolved in 134 mL of ultradry tetrahydrofuran and the reaction solution was cooled to −72 ° C. Next, an n-butyllithium solution (6.4 mL, 12.0 mmol) was added dropwise under the protection of nitrogen gas. After the dropping was completed, the temperature was continuously maintained for 30 minutes. Then, trimethylsilyltrifluoromethanesulfonate (TMSOTf) (4.2 g, 18.8 mmol) was added. After the addition was completed, the reaction was heated to room temperature and reacted for 2 hours. Then, a saturated sodium hydrogen carbonate solution was added to quench the reaction. Ethyl acetate was then added to the reaction and the solution was separated. The aqueous phase was extracted with ethyl acetate and combined with the organic phase. It was dried and rotated so as to completely remove the solvent by rotary evaporation to obtain a crude product. Separated by silica gel column chromatography (eluent is dichloromethane: petroleum ether = 1: 2, v / v), intermediate 14 (3.2 g, 62.7%) which is a white solid as a target product. Got

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 sustained under nitrogen gas protection. It was refluxed for 24 hours. After cooling to room temperature, the water in the solution was carefully spun off by rotary evaporation to give an iridium dimer of ethoxyethanol solution. It does not need to be further purified and can be used as it is for the next reaction.

Step 8: Synthesis of compound 73

Iridium dimer ethoxyethanol solution 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) was 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 put into a funnel filled with diatomaceous earth, filtered and washed with ethanol. Dichloromethane was added to the obtained solid and the filtrate was collected. Then ethanol is added to concentrate the resulting solution, but not until it is complete. After filtration, 1.2 g of the 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 a target product with a molecular weight of 1218.4.

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). In a 1 L reaction flask, 375 mL of 1,4-dioxane and 125 mL of water were added. The system was evacuated, replaced with nitrogen gas and refluxed overnight. After the reaction was detected by TLC, the mixture was cooled to room temperature, diluted with water, extracted with dichloromethane, and combined with an organic phase. Dry, rotary evaporate, and separated by silica gel column chromatography (eluting agent is ethyl acetate: petroleum ether = 1: 100, v / v), intermediate 15 (15.6 g, 15.6 g,) which is a colorless oily liquid. 39.8%) was obtained.

Step 2: Synthesis of intermediate 16

Intermediate 15 (15.6 g, 49.8 mmol) was dissolved in 200 mL of dichloromethane. Then, after cooling the reaction solution to 0 ° C., boron tribromide (18.7 g, 74.7 mmol) was gradually added. Then, the reaction was continued at the temperature for 2 hours. After the reaction was shown to be complete by TLC, water was carefully added to quench the reaction, extracted with dichloromethane and combined with the organic phase. Dry, rotary evaporate, and separated by silica gel column chromatography (eluting agent is ethyl acetate: petroleum ether = 1: 50, v / v), intermediate 16 (12.1 g, 81) which is a white solid. .2%) was obtained.

Step 3: Synthesis of Intermediate 17

Intermediate 16 (12.1 g, 40.5 mmol), potassium carbonate (11.2 g, 80.9 mmol) and DMF (150 mL) were added to a 500 mL three-necked flask in that order. Then, the obtained reaction mixture was heated at 100 ° C. under the protection of nitrogen gas and reacted overnight. After cooling the reaction mixture to room temperature, water and ethyl acetate were added, extracted and combined with the organic phase. The organic phase was washed with saturated brine multiple times, dried, and rotated to completely remove the solvent by rotary evaporation to obtain a crude product. Separation by silica gel column chromatography (the 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

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), in order in a 500 mL three-necked flask. Potassium acetate (5.2 g, 52.7 mmol) and 1,4-dioxane (300 mL) were added. The resulting reaction mixture was heated to reflux under the protection of nitrogen gas and reacted overnight. After the reaction was complete, the reaction mixture was cooled to room temperature, water and ethyl acetate were added, extracted, the solution was separated and the organic phase was merged. The organic phase was washed with saturated brine multiple times, dried, and rotated to completely remove the solvent by rotary evaporation to obtain a crude product. Separated by silica gel column chromatography (eluting agent is ethyl acetate: petroleum ether = 1: 50, v / v), intermediate 18 (9.5 g, 83.0%) which is a white solid as a target product. ) Was obtained.

Step 5: Synthesis of Intermediate 19

2-Chloro-6-bromoquinoline (5 g, 20.6 mmol) was dissolved in 40 mL of ultradry tetrahydrofuran and the reaction solution was cooled to −72 ° C. Next, an n-butyllithium solution (9 mL, 22.7 mmol) was added dropwise under the protection of nitrogen gas. After the dropping was completed, the temperature was continuously maintained for 30 minutes. Then, trimethylchlorosilane (TMSCl) (2.7 g, 24.7 mmol) was added, and after the addition was completed, the reaction was heated to room temperature and reacted for 2 hours. Then, a saturated sodium hydrogen carbonate solution was added to quench the reaction. 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 merged. It was dried and rotated so as to completely remove the solvent by rotary evaporation to obtain a crude product. Separated by silica gel column chromatography (eluting agent is ethyl acetate: petroleum ether = 1: 100, v / v), intermediate 19 (4.2 g, 86.5%) which is a white solid as a target product. ) Was obtained.

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.), respectively, in a 250 mL three-necked flask. 6 mmol), 1,4-dioxane (16 mL) and water (4 mL) were added and the resulting reaction mixture was heated to reflux under the protection of nitrogen gas and allowed to react overnight. The reaction mixture was cooled to room temperature and then filtered. The obtained solid was washed with water and petroleum ether multiple times in order and then dried to obtain a crude product. Separated by silica gel column chromatography (eluting agent is ethyl acetate: petroleum ether = 1: 100, v / v), intermediate 20 (1.28 g, 86.8%) which is a white solid as a target product. ) Was obtained.

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) sustained under nitrogen gas protection. Then, it was refluxed for 24 hours. After cooling to room temperature, the water in the solution was carefully spun off by rotary evaporation to give an iridium dimer of ethoxyethanol solution. It does not need to be further purified and can be used as it is for the next reaction.

Step 8: Synthesis of compound 128

50 mL round of 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). It was added to the bottom flask and reacted at 60 ° C. for 24 hours under the protection of nitrogen gas. Then, it was put into a funnel filled with diatomaceous earth, filtered and washed with ethanol. Dichloromethane was added to the obtained solid, and the filtrate was collected. Then ethanol is added to concentrate the resulting solution, but not until it is complete. 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 a target product with a molecular weight of 1214.4.

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) sustained under nitrogen gas protection. Then, it was refluxed for 24 hours. After cooling to room temperature, the water in the solution was carefully spun off by rotary evaporation to give an iridium dimer of ethoxyethanol solution. It does not need to be further purified and can be used as it is for the next reaction.

Step 2: Synthesis of compound 164

The iridium dimer ethoxyethanol solution 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). ) Was added to a 10 mL round bottom flask and reacted at 60 ° C. for 24 hours under the protection of nitrogen gas. Then, it was put into a funnel filled with diatomaceous earth, filtered and washed with ethanol. Dichloromethane was added to the obtained solid, and the filtrate was collected. Then ethanol is added to concentrate the resulting solution, but not until it is complete. After filtration, 780 mg of the 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 a target product with a molecular weight of 1228.4.

Example 5 of Synthesis: 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) in a 250 mL three-necked flask, respectively. .93 mmol), sodium carbonate (2.94 g, 27.8 mmol), 1,4-dioxane (80 mL) and water (20 mL) were added and the resulting reaction mixture was heated to reflux under the protection of nitrogen gas. And let it react overnight. The reaction mixture was cooled to room temperature and then filtered. The obtained solid was washed with water and petroleum ether multiple times in order and then dried to obtain a crude product. Separated by silica gel column chromatography (eluent is dichloromethane: petroleum ether = 1: 4, v / v), intermediate 21 (4.5 g, 57.3%) which is a white solid as a target product. Got

Step 2: Synthesis of Intermediate 22

Intermediate 21 (4.5 g, 10.6 mmol) was dissolved in 100 mL of ultradry tetrahydrofuran and the reaction solution was cooled to −72 ° C. Next, an n-butyllithium solution (5.1 mL, 12.8 mmol) was added dropwise under the protection of nitrogen gas. After the dropping was completed, the temperature was continuously maintained for 30 minutes. Then, trimethylsilyltrifluoromethanesulfonate (TMSOTf) (3.3 g, 14.8 mmol) was added. After the addition was completed, the reaction was heated to room temperature and reacted for 2 hours. Then, a saturated sodium hydrogen carbonate solution was added to quench the reaction. Ethyl acetate was then added to the reaction and the solution was separated. The aqueous phase was extracted with ethyl acetate and combined with the organic phase. It was dried and rotated so as to completely remove the solvent by rotary evaporation to obtain a crude product. Separated by silica gel column chromatography (eluent is dichloromethane: petroleum ether = 1: 3, v / v), intermediate 22 (3.37 g, 76.4%) which is a white solid as a target product. Got

Step 3: Synthesis of Intermediate 23

Intermediate 22 (3.37 g, 8.1 mmol), isobutylboric acid (1.65 g, 16.2 mmol), potassium palladium acetate (91 mg, 0.4 mmol), Refos (333 mg, 0.8 mmol) in a 250 mL three-necked flask, respectively. , Potassium Phosphate Trihydrate (6.47 g, 24.3 mmol) and toluene (60 mL) were added and the resulting reaction mixture was heated to reflux under the protection of nitrogen gas and allowed to react overnight. After cooling the reaction mixture to room temperature, it was placed in a funnel filled with diatomaceous earth, filtered, and the filtrate was collected and rotated to completely remove the solvent by rotary evaporation to obtain a crude product. Separated by silica gel column chromatography (eluent is dichloromethane: petroleum ether = 1: 3, v / v), intermediate 23 (3.1 g, 87.4%) which is a white solid as a target product. Got

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 sustained under nitrogen gas protection. It was refluxed for 24 hours. After cooling to room temperature, the water in the solution was carefully spun off by rotary evaporation to give an iridium dimer of ethoxyethanol solution. It does not need to be further purified and can be used as it is for the next reaction.

Step 5: Synthesis of compound 74

The iridium dimer ethoxyethanol solution 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 mmo) was 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 put into a funnel filled with diatomaceous earth, filtered and washed with ethanol. Dichloromethane was added to the obtained solid and the filtrate was collected. Then ethanol is added to concentrate the resulting solution, but not until it is complete. After filtration, 0.85 g of the 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 a target product with a molecular weight of 1330.5.

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) in a 250 mL three-necked flask, respectively. ), Sodium carbonate (2.97 g, 28.1 mmol), 1,4-dioxane (80 mL) and water (20 mL) are added and the resulting reaction mixture is heated to reflux under the protection of nitrogen gas. It was reacted in the evening. The reaction mixture was cooled to room temperature and then filtered. The obtained solid was washed with water and petroleum ether multiple times in order and then dried to obtain a crude product. Separated by silica gel column chromatography (eluent is dichloromethane: petroleum ether = 1: 5 and v / v), intermediate 24 (3.6 g, 45.6%) which is a white solid as a target product. Got

Step 2: Synthesis of Intermediate 25

Intermediate 24 (3.6 g, 8.52 mmol) was dissolved in 85 mL of ultradry tetrahydrofuran and the reaction solution was cooled to −72 ° C. Next, an n-butyllithium solution (4.1 mL, 10.2 mmol) was added dropwise under the protection of nitrogen gas. After the dropping was completed, the temperature was continuously maintained for 30 minutes. Then, trimethylsilyltrifluoromethanesulfonate (TMSOTf) (2.64 g, 11.9 mmol) was added. After the addition was completed, the reaction was heated to room temperature and reacted for 2 hours. Then, a saturated sodium hydrogen carbonate solution was added to quench the reaction. Ethyl acetate was then added to the reaction and the solution was separated. The aqueous phase was extracted with ethyl acetate and combined with the organic phase. It was dried and rotated so as to completely remove the solvent by rotary evaporation to obtain a crude product. Separated by silica gel column chromatography (eluent is dichloromethane: petroleum ether = 1: 4, v / v), intermediate 25 (1.8 g, 50.8%) which is a white solid as a target product. Got

Step 3: Synthesis of Intermediate 26

Intermediate 25 (1.8 g, 4.3 mmol), isobutylboric acid (0.88 g, 8.65 mmol), potassium acetate (49 mg, 0.22 mmol), Refos (181 mg, 0.43 mmol) in a 100 mL three-necked flask, respectively. , Potassium Phosphate Trihydrate (3.46 g, 13.0 mmol) and toluene (30 mL) were added and the resulting reaction mixture was heated to reflux under the protection of nitrogen gas and allowed to react overnight. After cooling the reaction mixture to room temperature, it was placed in a funnel filled with diatomaceous earth, filtered, and the filtrate was collected and rotated to completely remove the solvent by rotary evaporation to obtain a crude product. Separated by silica gel column chromatography (eluent is dichloromethane: petroleum ether = 1: 3 and v / v), intermediate 26 (1.74 g, 91.8%) which is a white solid as a target product. Got

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) sustained under nitrogen gas protection. Then, it was refluxed for 24 hours. After cooling to room temperature, the water in the solution was carefully spun off by rotary evaporation to give an iridium dimer of ethoxyethanol solution. It does not need to be further purified and can be used as it is for the next reaction.

Step 5: Synthesis of compound 122

50 mL round of 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). It was added to the bottom flask and reacted at room temperature for 24 hours under the protection of nitrogen gas. Then, it was put into a funnel filled with diatomaceous earth, filtered and washed with ethanol. Dichloromethane was added to the obtained solid and the filtrate was collected. Then ethanol is added to concentrate the resulting solution, but not until it is complete. 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 a target product with a molecular weight of 1290.6.

Example 7 of Synthesis: 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) sustained under nitrogen gas protection. Then, it was refluxed for 24 hours. After cooling to room temperature, the water in the solution was carefully spun off by rotary evaporation to give an iridium dimer of ethoxyethanol solution. It does not need to be further purified and can be used as it is for the next reaction.

Step 2: Synthesis of compound 110

100 mL round of 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). Add to bottom flask. The reaction was carried out at room temperature for 24 hours under the protection of nitrogen gas. Then, it was put into a funnel filled with diatomaceous earth, filtered and washed with ethanol. Dichloromethane was added to the obtained solid and the filtrate was collected. Then ethanol is added to concentrate the resulting solution, but not until it is complete. After filtration, 0.15 g of the 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 a target product with a molecular weight of 1290.6.

Example 8 of synthesis: 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) in nitrogen gas. It was continuously refluxed for 24 hours under protection. After cooling to room temperature, the water in the solution was carefully spun off by rotary evaporation to give an iridium dimer of ethoxyethanol solution. It does not need to be further purified and can be used as it is for the next reaction.

Step 2: Synthesis of compound 307

Iridium dimer ethoxyethanol solution 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). Was 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 put into a funnel filled with diatomaceous earth, filtered and washed with ethanol. Dichloromethane was added to the obtained solid and the filtrate was collected. Then ethanol is added to concentrate the resulting solution, but not until it is complete. After filtration, 0.44 g of the 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 a target product with a molecular weight of 1304.6.

Example 9 of Synthesis: 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) under nitrogen gas protection. It was continuously refluxed for 24 hours. After cooling to room temperature, the water in the solution was carefully spun off by rotary evaporation to give an iridium dimer of ethoxyethanol solution. It does not need to be further purified and can be used as it is for the next reaction.

Step 2: Synthesis of compound 311

The iridium dimer ethoxyethanol solution 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). Was 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 put into a funnel filled with diatomaceous earth, filtered and washed with ethanol. Dichloromethane was added to the obtained solid and the filtrate was collected. Then ethanol is added to concentrate the resulting solution, but not until it is complete. 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 a target product with a molecular weight of 1196.5.

Example 10 of Synthesis: 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) sustained under nitrogen gas protection. Then, it was refluxed for 24 hours. After cooling to room temperature, the water in the solution was carefully spun off by rotary evaporation to give an iridium dimer of ethoxyethanol solution. It does not need to be further purified and can be used as it is for the next reaction.

Step 2: Synthesis of compound 304

100 mL round of 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). It was added to the bottom flask and reacted at room temperature for 24 hours under the protection of nitrogen gas. Then, it was put into a funnel filled with diatomaceous earth, filtered and washed with ethanol. Dichloromethane was added to the obtained solid and the filtrate was collected. Then ethanol is added to concentrate the resulting solution, but not until it is complete. After filtration, compound 304 (yield 72.6%) is 640 mg of product. The product was further purified by column chromatography. The structure of the compound was confirmed by NMR and LC-MS as a target product with a molecular weight of 1296.6.

Example 11 of Synthesis: 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 sustained under nitrogen gas protection. It was refluxed for 24 hours. After cooling to room temperature, the water in the solution was carefully spun off by rotary evaporation to give an iridium dimer of ethoxyethanol solution. It does not need to be further purified and can be used as it is for the next reaction.

Step 2: Synthesis of compound 313

100 mL round of 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). It was added to the bottom flask and reacted at room temperature for 24 hours under the protection of nitrogen gas. Then, it was put into a funnel filled with diatomaceous earth, filtered and washed with ethanol. Dichloromethane was added to the obtained solid and the filtrate was collected. Then ethanol is added to concentrate the resulting solution, but not until it is complete. 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 a target product with a molecular weight of 1326.5.

Those skilled in the art should know that the above preparation method is merely exemplary and can be modified to obtain the structure of other compounds of the invention.

Spectral data

Photoluminescence spectrum (PL) data of the compound and the comparative compound in the present invention were measured using a fluorescence spectrophotometer of Shanghai ▲ Ryo ▼ Optical Technology Co., Ltd. with the model number ▲ Ryo ▼ Optical F98. The samples in Examples and Comparative Examples ^{were prepared in a solution having a concentration of 3 × 10-5} mol / L with dichloromethane at HPLC level, respectively, and then excited with light having a wavelength of 500 nm at room temperature (298K) to obtain the radiation spectrum thereof. Was measured. The measurement results are shown in Table 1.

Example 1 of the element
First, a glass substrate having an indium tin oxide (ITO) anode having a thickness of 120 nm was washed, 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 the substrate holder and placed in a vacuum chamber. Hereinafter, when the degree of vacuum was about ^10-8 torr, the designated organic layer was vapor-deposited on the ITO anode in order by hot vacuum-deposited at a rate of 0.2 to 2 angstroms / sec. Compound HI was used as the hole injection layer (HIL). Compound HT is used as the hole transport layer (HTL). Compound EB was used as the electron blocking layer (EBL). Then, the compound 77 in the present invention was doped with the host compound RH and used as a light emitting layer (EML). Compound HB was used as the hole blocking layer (HBL). The compound ET and 8-hydroxyquinoline-lithium (Liq) were co-deposited on the HBL as an electron transport layer (ETL). Finally, Liq having a thickness of 1 nm was deposited as an electron injection layer, and Al having a thickness of 120 nm was deposited as a cathode. Then, the element was transferred to a glove box and encapsulated with a glass cover and a hygroscopic agent to complete the element.

Example 2 of the element
The method for preparing Example 2 of the device is the same as that of Example 1 of the device except that the compound 128 according to the present invention replaces the compound 77 according to the present invention in the light emitting layer (EML).

Example 3 of the element
The method for preparing Example 3 of the device is the same as that of Example 1 of the device except that the compound 164 according to the present invention replaces the compound 77 according to the present invention in the light emitting layer (EML).

Example 4 of the element
The method for preparing Example 4 of the device is the same as that of Example 1 of the device except that the compound 73 according to the present invention replaces the compound 77 according to the present invention in the light emitting layer (EML).

Example 5 of the element
The method for preparing Example 5 of the device is the same as that of Example 1 of the device except that the compound 74 according to the present invention replaces the compound 77 according to the present invention in the light emitting layer (EML).

Example 6 of the element
In the preparation method of Example 6 of the device, the compound 122 according to the present invention is substituted for the compound 77 according to the present invention in the light emitting layer (EML), and the weight ratio of the compound 122 to the compound RH is 2.5: 97.5. It is the same as the first embodiment of the element except that.

Example 7 of the element
The method for preparing Example 7 of the device is the same as that of Example 1 of the device except that the compound 307 according to the present invention replaces the compound 77 according to the present invention in the light emitting layer (EML).

Example 8 of the element
The method for preparing Example 8 of the device is the same as that of Example 6 of the device, except that the compound 304 according to the present invention replaces the compound 122 according to the present invention in the light emitting layer (EML).

Example 9 of the element
The method for preparing Example 9 of the device is the same as that of Example 1 of the device except that the compound 311 according to the present invention replaces the compound 77 according to the present invention in the light emitting layer (EML).

Element comparison example 1
The method for preparing Comparative Example 1 of the device is the same as that of Example 1 of the device except that the compound 77 according to the present invention is replaced with the comparative compound in the light emitting layer (EML).

The layer structure and thickness of the device are shown in the table below. Layers with more than one material used can be obtained by doping different compounds by weight.

The structure of the material used for the device is expressed as follows.

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

As can be seen from Summary Table 1, in the structure of the ligand L _a of the present application, the introduction of the silyl substituent has effectively, is clearly dark red area red shift the emission wavelength of the material from the shallow red region. At the same time, the CIE and λ _max in Table 3 further demonstrated this. Also, by observing the voltage, FWHM and EQE data in Table 3, it was discovered that the introduction of a silyl substituent clearly improves its external quantum efficiency while maintaining a similar low voltage and narrow full width at half maximum. It has been shown that the silyl substituent has an action of changing the emission wavelength and improving the luminous efficiency in the compound according to the present invention.

Of the above comparisons, Example 4 and Comparative Example 1 are the most direct comparisons. Luminescent material in Example 4 is a compound 73, the light emitting material in Comparative Example 1 is the comparative compound, PL lambda _max of the compound 73 is 622nm, PLλ _max comparison compound is 609 nm. In the device, their CIExs are 0.678 and 0.655, respectively, and the efficiencies are 21.25% and 20.33%, respectively. The data reliably demonstrated the predominance of the silyl substituent. Further, in the light emitting materials used in Examples 1 to 8, the silyl substituent is introduced at a different position. For example, in Examples 2, 3 and 7, the silyl group was substituted on the benzene ring on the quinoline ring, and in Examples 1, 4, 5, 6 and 8, the silyl group was on the pyridine ring on the quinoline ring. It was replaced with. 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 indicate that the red shift that occurred when the silyl group was substituted on the benzene ring on the quinoline ring occurred when the silyl group was substituted on the pyridine ring on the quinoline ring. By demonstrating that it is slightly less than the red shift, and adjusting the substitution position of the silyl group in the quinoline ring, it is possible to realize the excellent effect of fine-tuning the element CIE while realizing deep red emission. I proved that I could do it. Further, the EQE reaching 25.19% in Example 7 proved that high device efficiency can be provided when the silyl group is replaced with the benzene ring in the quinoline ring.

The compound 311 as a light emitting material in Example 9 has a fluorine substitution in the quinoline ring, and its PLλ _max is 614 nm. The CIE data of the device also proved that deep red radiation can be realized. The device efficiency reaching 24.28% proved that fluorine substitution also had a good effect.

In short, the metal complex according to the present invention 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. can do.

It should be understood that the various examples described herein are merely exemplary and are not intended to limit the scope of the invention. Therefore, it is obvious to those skilled in the art that the invention to be protected includes modifications of the specific examples and preferred embodiments described herein. Many of the materials and structures described herein can be replaced by other materials and structures, provided that they do not deviate from the concept of the present invention. It should be understood that the various theories as to why the present invention works are not limiting.

Claims (27)

A metal complex having a maximum radiation wavelength of 612 nm or more, preferably 615 nm or more in the photoluminescence spectrum (PL).
Metal in the metal complex, the relative atomic mass is selected from 40 than the metal, and containing a ligand L _a having the structure represented by Formula 1, the metal complex.

(Z is selected from O,
X _{1 to} X ₈ are selected from _{C, CR x} or N, which are the same or different for each appearance.
Y _{1 to Y 6 are selected from CR y} or N, which are the same or different for each appearance.
R _x and R _y are the same or different each time they appear, such as hydrogen, dehydrogen, halogen, an alkyl group having 1 to 20 substituted or unsubstituted carbon atoms, and a cyclo having 3 to 20 substituted or unsubstituted ring carbon atoms. Alkyl group, substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted. Or an unsubstituted 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, substituted or unsubstituted. Heteroaryl group with 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group with 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group with 6 to 20 carbon atoms, substituted or unsubstituted carbon atom Selected from the group consisting of an amine group, 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 a combination thereof. ,
Adjacent substituents R _x may be bonded to form a ring. ) The metal complex further comprises a ligand L _b having a structure represented by the following formula, a metal complex according to claim 1.

(R _{1 to} R ₇ are the same or different at each appearance of hydrogen, dehydrogen, halogen, an alkyl group having 1 to 20 substituted or unsubstituted carbon atoms, and 3 to 20 substituted or unsubstituted ring carbon atoms. Cycloalkyl groups, substituted or unsubstituted heteroalkyl groups with 1 to 20 carbon atoms, substituted or unsubstituted aralkyl groups with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups with 1 to 20 carbon atoms, Substituent or unsubstituted aryloxy group with 6 to 30 carbon atoms, substituted or unsubstituted alkenyl group with 2 to 20 carbon atoms, substituted or unsubstituted aryl group with 6 to 30 carbon atoms, substituted or unsubstituted Heteroaryl group with 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group with 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group with 6 to 20 carbon atoms, substituted or unsubstituted carbon Select from the group consisting of an amine group, 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 a combination thereof having 0 to 20 atoms. Re,
Preferably, _{at least one or two of R 1 to} R ₃ are substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, and substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms. , substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms or selected from combinations thereof, and / or R ₄ at least one of to R ₆ is a substituted or unsubstituted carbon atoms 1, ~ 20 alkyl groups, substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, or a combination thereof.
More preferably, _{at least two of R 1 to} R ₃ are substituted or unsubstituted alkyl groups having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms, substituted. or unsubstituted heteroalkyl group having 2 to 20 carbon atoms or selected from combinations thereof, and / or at least two of R ₄ to R ₆ is a substituted or unsubstituted 2-20 carbon atoms It is selected from an alkyl group, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 20 carbon atoms, or a combination thereof. ) Y ₁ to Y ₆ are the same or different at each occurrence selected from _CR y1, _{CR y2} or N, and at least one of _Y 1 to Y ₆ is selected from _{CR y2,} wherein _{R y2} is -L-SiR _s1 R _s2 R _s3 structure,
R _y1 , R _s1 , R _s2 , and R _s3 are the same or different at each appearance, such as hydrogen, heavy hydrogen, halogen, an alkyl group having 1 to 20 substituted or unsubstituted carbon atoms, and a substituted or unsubstituted ring carbon atom. Cycloalkyl group number 3 to 20, substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted carbon atom number 1 to 20 alkoxy groups, substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups with 2 to 20 carbon atoms, substituted or unsubstituted aryl groups with 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, substituted. Alternatively, an 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 a combination thereof. Selected from a group of
L is a single-bonded, substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, or substituted or unsubstituted arylene having 6 to 20 carbon atoms. Selected from groups, substituted or unsubstituted heteroarylene groups having 3 to 20 carbon atoms, or combinations thereof.
The metal complex according to claim 1, wherein the adjacent substituents R _s1 , R _s2 , and R _s3 may be bonded to each other to form a ring. At least one of _{X 1 to} X ₈ and Y _{1 to Y 6 is selected from CR x} or CR _y , and the R _x , R _y are the same or different with each appearance, with the same or different heavy hydrogen, halogens, substitutions. Or an unsubstituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted group. Aralkyl group with 7 to 30 substituted carbon atoms, alkoxy group with 1 to 20 substituted or unsubstituted carbon atom, aryloxy group with 6 to 30 substituted or unsubstituted carbon atom, substituted or unsubstituted carbon atom Alkenyl groups of 2 to 20, substituted or unsubstituted aryl groups of 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups of 3 to 30 carbon atoms, substituted or unsubstituted carbon atoms of 3 to 20 Alkylsilyl group, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted amine group having 0 to 20 carbon atoms, 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 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 the R _x , R _y are the same or the same for each appearance. Differently heavy hydrogen, halogen, substituted or unsubstituted alkyl groups with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups with 3 to 20 ring carbon atoms, substituted or unsubstituted carbon atoms 1 to 20 Heteroalkyl groups, substituted or unsubstituted aralkyl groups with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups with 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms. , Substituent or unsubstituted alkenyl group with 2 to 20 carbon atoms, substituted or unsubstituted aryl group with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group with 3 to 30 carbon atoms, substituted or unsubstituted. Substituent alkylsilyl groups with 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups with 6 to 20 carbon atoms, substituted or unsubstituted amine groups with 0 to 20 carbon atoms, acyl groups, carbonyl groups, The metal complex according to claim 1, which is selected from the group consisting of 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 a combination thereof. Metal in the metal complex, the relative atomic mass is selected from 40 than the metal, containing a ligand L _a having the structure Ararasa the formula 1 ', the metal complex.

(Z is selected from O, S or Se,
X _{1 to} X ₈ are selected from _{C, CR x} or N, which are the same or different for each appearance.
Y ₁ to Y ₆ are the same or different at each occurrence selected from _CR y1, _{CR y2} or N, and at least one of _Y 1 to Y ₆ is selected from _{CR y2,} wherein _{R y2} is -L-SiR _s1 R _s2 R _s3 structure,
R _x , R _y1 , R _s1 , R _s2 , and R _s3 are the same or different at each appearance, hydrogen, dehydrogen, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted. Cycloalkyl group with 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl group with 1 to 20 carbon atoms, substituted or unsubstituted aralkyl group with 7 to 30 carbon atoms, substituted or unsubstituted carbon atom An alkoxy group having 1 to 20, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, an alkenyl group having 2 to 20 substituted or unsubstituted carbon atoms, and 6 to 30 substituted or unsubstituted carbon atoms. Aryl group, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms. Group, substituted or unsubstituted amine group with 0 to 20 carbon atoms, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxyl group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group and Selected from the group consisting of these combinations
L is a single-bonded, substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, or substituted or unsubstituted arylene having 6 to 20 carbon atoms. Selected from the group consisting of groups, substituted or unsubstituted heteroarylene groups having 3 to 20 carbon atoms, or combinations thereof.
Adjacent substituents R _x , R _s1 , R _s2 , and R _s3 may be combined to form a ring. ) Two adjacent two of X _{1 to} X ₄ are C, and one said C is bonded to the metal by a carbon-metal bond and is adjacent to the carbon-metal bond of _{X 1 to} X _4. One is _{selected from CR x} , wherein the R _x is a heavy hydrogen, halogen, an alkyl group having 1 to 20 substituted or unsubstituted carbon atoms, and a cyclo having 3 to 20 substituted or unsubstituted ring carbon atoms. Alkyl group, substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted. Or an unsubstituted 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, substituted or unsubstituted. Heteroaryl group with 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group with 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group with 6 to 20 carbon atoms, substituted or unsubstituted carbon atom Claimed to be selected from a group of several to 20 amine groups, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, sulfanyl groups, sulfinyl groups, sulfonyl groups, phosphino groups and combinations thereof. The metal complex according to 1 or 5. At least one of _{X 1 to} X ₈ and Y _{1 to Y 6 is selected from CR x} or CR _{y 1} , said R _x , R _{y 1} may be the same or different with each appearance of dehydrogen, halogen, substitution or An unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted group. Aralkyl group having 7 to 30 carbon atoms, alkoxy group having 1 to 20 substituted or unsubstituted carbon atoms, aryloxy group having 6 to 30 substituted or unsubstituted carbon atoms, substituted or unsubstituted carbon atom number 2 to 20 alkenyl groups, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups with 3 to 30 carbon atoms, substituted or unsubstituted carbon atoms 3 to 20 Alkylsilyl group, substituted or unsubstituted arylsilyl group with 6 to 20 carbon atoms, substituted or unsubstituted amine group with 0 to 20 carbon atoms, acyl group, carbonyl group, carboxyl group, ester group, cyano group, Selected from the group consisting of an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group and a combination thereof.
Preferably, 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 1} , and the R _x , R _{y 1} are the same or the same for each appearance. Differently heavy hydrogen, halogen, substituted or unsubstituted alkyl groups with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups with 3 to 20 ring carbon atoms, substituted or unsubstituted carbon atoms 1 to 20 Heteroalkyl groups, substituted or unsubstituted aralkyl groups with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups with 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms. , Substituent or unsubstituted alkenyl group with 2 to 20 carbon atoms, substituted or unsubstituted aryl group with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group with 3 to 30 carbon atoms, substituted or unsubstituted. Substituent alkylsilyl groups with 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups with 6 to 20 carbon atoms, substituted or unsubstituted amine groups with 0 to 20 carbon atoms, acyl groups, carbonyl groups, The metal complex according to claim 5, which is selected from the group consisting of 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 a combination thereof. Wherein L _a has a structure represented by Formula 2, the metal complex according to claim 5.

(Z is selected from O, S or Se,
X _{3 to} X _{8 are selected from CR x} or N, which are the same or different for each appearance.
Y ₁ to Y ₆ are the same or different at each occurrence selected from _CR y1, _{CR y2} or N, and at least one of _Y 1 to Y ₆ is selected from _{CR y2,} wherein _{R y2} is -L-SiR _s1 R _s2 R _s3 structure,
R _x , R _y1 , R _s1 , R _s2 , and R _s3 are the same or different at each appearance, hydrogen, dehydrogen, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted. Cycloalkyl group with 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl group with 1 to 20 carbon atoms, substituted or unsubstituted aralkyl group with 7 to 30 carbon atoms, substituted or unsubstituted carbon atom An alkoxy group having 1 to 20, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, an alkenyl group having 2 to 20 substituted or unsubstituted carbon atoms, and 6 to 30 substituted or unsubstituted carbon atoms. Aryl group, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms. Group, substituted or unsubstituted amine group with 0 to 20 carbon atoms, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxyl group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group and Selected from the group consisting of these combinations
L is a single-bonded, substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, or substituted or unsubstituted arylene having 6 to 20 carbon atoms. Selected from groups, substituted or unsubstituted heteroarylene groups having 3 to 20 carbon atoms, or combinations thereof.
Adjacent substituents R _x , R _s1 , R _s2 , and R _s3 may be combined to form a ring. ) Y ₁ to Y ₂ is selected from the same or different and _{CR y1} or N on each _occurrence, Y 3 to Y ₆ is selected from the same or different at each occurrence _CR y1, _{CR y2} or N, and _{Y 3} At least one of ~ Y _{6 is selected from CR y2} , wherein the R _y2 has a structure of −L—SiR _s1 R _s2 R _s3.
Ry1 is the same or different at each appearance of hydrogen, dehydrogen, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, Substituted or unsubstituted heteroalkyl group with 1 to 20 carbon atoms, substituted or unsubstituted aralkyl group with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy group with 1 to 20 carbon atoms, substituted or unsubstituted Aryloxy group having 6 to 30 carbon atoms, an alkenyl group having 2 to 20 substituted or unsubstituted carbon atoms, an aryl group having 6 to 30 substituted or unsubstituted carbon atoms, and a substituted or unsubstituted carbon atom number. 3 to 30 heteroaryl groups, substituted or unsubstituted amine groups with 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, sulfanyl groups, sulfinyl groups, Selected from the group consisting of sulfonyl groups, phosphino groups and combinations thereof,
R _s1 , R _s2 , and R _s3 are the same or different each time they appear, and each of them is hydrogen, dehydrogen, halogen, an alkyl group having 1 to 20 substituted or unsubstituted carbon atoms, and 3 to 3 substituted or unsubstituted ring carbon atoms. 20 cycloalkyl groups, substituted or unsubstituted heteroalkyl groups with 1 to 20 carbon atoms, substituted or unsubstituted aralkyl groups with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy with 1 to 20 carbon atoms Group, substituted or unsubstituted aryloxy group with 6 to 30 carbon atoms, substituted or unsubstituted alkenyl group with 2 to 20 carbon atoms, substituted or unsubstituted aryl group with 6 to 30 carbon atoms, substituted or Unsubstituted heteroaryl group with 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group with 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group with 6 to 20 carbon atoms, substituted or unsubstituted A group consisting of an amine group, 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 a combination thereof having 0 to 20 carbon atoms. Selected from
L is a single-bonded, substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, or substituted or unsubstituted arylene having 6 to 20 carbon atoms. Selected from groups, substituted or unsubstituted heteroarylene groups having 3 to 20 carbon atoms, or combinations thereof.
Adjacent substituents R _s1 , R _s2 , and R _s3 may be bonded to form a ring.
Preferably, R _s1 , R _s2 , and R _s3 are the same or differently substituted or different alkyl groups having 1 to 20 carbon atoms, and substituted or unsubstituted cycloalkyls having 3 to 20 ring carbon atoms at each appearance. Group, substituted or unsubstituted heteroalkyl group with 1 to 20 carbon atoms, substituted or unsubstituted aralkyl group with 7 to 30 carbon atoms, substituted or unsubstituted alkoxy group with 1 to 20 carbon atoms, substituted or Unsubstituted aryloxy groups with 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups with 2 to 20 carbon atoms, substituted or unsubstituted aryl groups with 6 to 30 carbon atoms, substituted or unsubstituted carbon The metal complex according to any one of claims 1 to 3 to 8, which is selected from the group consisting of heteroaryl groups having 3 to 30 atoms and combinations thereof. The metal complex _has the structure of _{M (L a) m (L} b) n (L c) q,
However, the metal M is selected from Ir, Rh, Re, Os, Pt, Au or Cu, and preferably the metal M is selected from Ir, Pt or Os.
L _a , L _b and L _c are the first ligand, the second ligand and the third ligand of the complex, respectively, m is selected from 1, 2 or 3, and 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.
If m is greater than 1, the plurality of L _a, which may be the same or different, when n is 2, the two L _b, which may be the same or different, and when q is 2, the two L _c may be the same or different
L _{a, L b} and _{L c,} which may be bonded to form a multidentate ligand,
L _b and L _c are selected from the group consisting of the following structures, which are the same or different for each appearance.

R _a , R _b and R _c represent one-substitution, multiple-substitution, or no-substitution, which are the same or different for each appearance.
X _b is selected O on each occurrence identical or different, S, Se, from the group consisting of _{NR N1} and _CR C1 _{R C2,}
X _c and X _d are selected from the group consisting of _{O, S, Se and NR N2} , which are the same or different for each appearance.
R _a , R _b , R _c , _RN1 , _RN2 , _RC1 and _RC2 are the same or different alkyl groups with hydrogen, dehydrogen, halogen, substituted or unsubstituted carbon atoms 1 to 20 at each appearance. , Substitutable or unsubstituted cycloalkyl group with 3 to 20 carbon atoms, substituted or unsubstituted heteroalkyl group with 1 to 20 carbon atoms, substituted or unsubstituted aralkyl group with 7 to 30 carbon atoms, substituted Alternatively, an unsubstituted 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 alkenyl group. An aryl group having 6 to 30 carbon atoms, a heteroaryl group having 3 to 30 substituted or unsubstituted carbon atoms, an alkylsilyl group having 3 to 20 substituted or unsubstituted carbon atoms, and a substituted or unsubstituted carbon atom number. 6 to 20 arylsilyl groups, substituted or unsubstituted amine groups with 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, sulfanyl groups, sulfinyl groups, Selected from the group consisting of sulfonyl groups, phosphino groups and combinations thereof,
Adjacent substituents _{R a, R b, R c} , R N1, R N2, R C1 and _{R C2} may combine to form a ring, any one of claims 1,3～9 The metal complex according to. The metal complex _has the structure of _{M (L a) m (L} b) n (L c) q,
However, the metal M is Ir, Rh, Re, Os, Pt, selected from Au, or _Cu, L a, _{L b} and _{L c} are first ligand of each of the complex, second ligand and the 3 ligands, 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 the oxidation of the metal M. Equal to the state,
If m is greater than 1, the plurality of L _a, which may be the same or different, when n is 2, the two L _b, which may be the same or different, and when q is 2, the two L _c may be the same or different, L _a, L _b and L _c, which may be bonded to form a multidentate ligand, L _b, which may be the same or different of the following on each occurrence Selected from the structure,

X _c and X _d are selected from the group consisting of _{O, S, Se and NR N2} , which are the same or different for each appearance.
R _a1 , R _b1 , R _c1 , and _RN2 are the same or different each time they appear, such as hydrogen, dehydrogen, halogen, an alkyl group having 1 to 20 substituted or unsubstituted carbon atoms, and a substituted or unsubstituted ring carbon atom. Cycloalkyl group number 3 to 20, substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted carbon atom number 1 to 20 alkoxy groups, substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups with 2 to 20 carbon atoms, substituted or unsubstituted aryl groups with 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, substituted. Alternatively, an 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 a combination thereof. Selected from a group of
Adjacent substituents R _a1 , R _b1 and R _c1 may be bonded to form a ring.
L _c is selected from the group consisting of the following structures, which are the same or different for each appearance.

R _a , R _b , and R _c represent one-substitution, multiple substitution, or no substitution, which are the same or different for each appearance.
X _e is selected from the group consisting of _{O, S, Se and NR N3} , which is the same or different for each appearance.
R _a , R _b , R _c , and _{RN 3} are the same or different at each appearance, such as hydrogen, dehydride, halogen, an alkyl group having 1 to 20 substituted or unsubstituted carbon atoms, and a substituted or unsubstituted ring carbon atom. Cycloalkyl group number 3 to 20, substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted carbon atom number 1 to 20 alkoxy groups, substituted or unsubstituted aryloxy groups with 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups with 2 to 20 carbon atoms, substituted or unsubstituted aryl groups with 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, substituted. Alternatively, an 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 a combination thereof. Selected from a group of
The metal complex according to any one of claims 1 to 3, wherein the adjacent substituents R _b and R _{c may be bonded to each other to form a ring.} The metal complex according to claim 10, wherein the metal complex has a structure represented by the formula 3.

(M is 1 or 2 and
Z is O,
X _{3 to} X _{8 are selected from CR x} or N, which are the same or different for each appearance.
Y ₁ to Y ₆ are the same or different at each occurrence selected from _CR y1, _{CR y2} or N, and at least one of _Y 1 to Y ₆ is selected from _{CR y2,} wherein _{R y2} is -L-SiR _s1 R _s2 R _s3 structure,
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 the same or different for each appearance. , Substituent or unsubstituted alkyl group with 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group with 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl group with 1 to 20 carbon atoms, substituted Or an unsubstituted 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, substituted or unsubstituted. An alkenyl group having 2 to 20 carbon atoms, an aryl group having 6 to 30 substituted or unsubstituted carbon atoms, a heteroaryl group having 3 to 30 substituted or unsubstituted carbon atoms, and 3 substituted or unsubstituted carbon atoms. Up to 20 alkylsilyl groups, substituted or unsubstituted arylsilyl groups with 6 to 20 carbon atoms, substituted or unsubstituted amine groups with 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxyl groups, ester groups, Selected from the group consisting of a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group and a combination thereof.
L is a single-bonded, substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, or substituted or unsubstituted arylene having 6 to 20 carbon atoms. Selected from groups, substituted or unsubstituted heteroarylene groups having 3 to 20 carbon atoms, or combinations thereof.
Adjacent substituents R _x , R _s1 , R _s2 , and R _s3 may be combined to form a ring.
Adjacent substituents R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ and R ₇ may be combined to form a ring.
Preferably, _{at least one or two of R 1 to} R ₃ are substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, and substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms. , substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms or selected from combinations thereof, and / or R ₄ at least one of to R ₆ is a substituted or unsubstituted carbon atoms 1, ~ 20 alkyl groups, substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, or a combination thereof.
More preferably, _{at least two of R 1 to} R ₃ are substituted or unsubstituted alkyl groups having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms, substituted or substituted. Alkyl groups having 2 to 20 carbon atoms unchanged or selected from combinations thereof, and / or _{at least two of R 4 to} R ₆ are substituted or unsubstituted alkyl groups having 2 to 20 carbon atoms. , A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 20 carbon atoms, or a combination thereof. ) The metal complex according to any one of claims 5 to 12, wherein Y _{1 to Y 6} are independently _{selected from CR y1} or CR _{y2, respectively.} The metal complex according to any one of claims 5 to 12, wherein at least one of Y _{1 to Y 6 is selected from N.} At _{least one of X 3 to} X ₈ is selected from N,
Preferably, at least one of _{X 3 to} X _{8 is selected from N.}
More preferably, the metal complex according to any one of claims 5 to 12 _{, wherein X 8 is N.} X _{3 to} X ₈ are independently selected from _{CR x, respectively.}
Preferably, the _Rx is hydrogen, dehydrogen, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted or non-substituted. Selected from substituted alkylsilyl groups with 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups with 6 to 20 carbon atoms, cyano groups, or combinations thereof.
More preferably, the _Rx is hydrogen, dehydrogen, fluorine, methyl group, ethyl group, isopropyl group, isobutyl group, tert-butyl group, neopentyl group, cyclopentyl group, cyclopentylmethyl group, cyclohexyl group, norbol group, adamantyl. The metal complex according to any one of claims 5 to 12, selected from the group consisting of a group, a trimethylsilyl group, an isopropyldimethylsilyl group, a phenyldimethylsilyl group, a trifluoromethyl group, a cyano group, and a combination thereof. X ₃ is _{selected from CR x} , wherein the R _x is hydrogen, dehydrogen, halogen, substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, substituted or unsubstituted ring carbon atom with 3 to 20 atoms. Selected from cycloalkyl groups, substituted or unsubstituted alkylsilyl groups with 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups with 6 to 20 carbon atoms, cyano groups, or combinations thereof.
Preferably, the _Rx is deuterium, halogen, an substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a cyano group, or these. Selected from the combination of
More preferably, the metal complex according to any one of claims 5 to 12 _{, wherein R x is selected from a methyl group or a deuterated methyl group.} At least one of Y ₁ to Y ₆ is selected from _{CR y2, R y2 has} the structure of a _{-L-SiR s1 R s2 R s3} ,
However, L is selected from a single bond, and R _s1 , R _s2 and R _s3 are independently substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, and substituted or unsubstituted ring carbon atoms 3 respectively. Selected from the group consisting of ~ 20 cycloalkyl groups, substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, and combinations thereof.
Preferably, _{Y 2} and / or _{Y 4} is selected from _{CR y2,} and at least one or two or three of _{R s1, R s2} and _{R s3} is a substituted or unsubstituted independently The metal complex according to any one of claims 5 to 17, selected from an alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, or a combination thereof. .. At least one of Y ₁ to Y ₆ is selected from _{CR y2, R y2 has} the structure of a _{-L-SiR s1 R s2 R s3} ,
However, L is selected from a single bond, and R _s1 , R _s2 and R _s3 are independently methyl group, ethyl group, isopropyl group, isobutyl group, tert-butyl group, neopentyl group, cyclopentyl group and cyclopentylmethyl. Selected from the group consisting of a group, a cyclohexyl group, a norbol group, an adamantyl group, a trifluoromethyl group, a phenyl group, and a combination thereof.
The metal complex according to claim 18. L _a is any one selected from the group consisting of _L a1 _{~L a1611} same or different in each _occurrence, specific structure of _{L a1 ~L} a1611 is represented as follows, claims The metal complex according to 1 or 5.

(In the structure of the _{^{L a1 ~L a1507, R a1 ~R}} a9 are each following groups.)

The metal complex according to any one of claims 10 to 20, wherein L _b is selected from the following structures, which are the same or different each time they appear.

(R _{1 to} R ₇ are independently hydrogen, deuterium, halogen, an alkyl group having 1 to 20 substituted or unsubstituted carbon atoms, and a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms. , Cyano groups, and combinations thereof.
Adjacent substituents R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ and R ₇ may be combined to form a ring.
Preferably, R _{1 to} R ₇ are independently hydrogen, dehydrogen, fluorine, methyl group, ethyl group, propyl group, isopropyl group, isobutyl group, n-butyl group, tert-butyl group and n-pentyl group, respectively. , Isopentyl group, neopentyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cyano group, and a combination thereof. ) The metal complex according to any one of claims 10 to 21, wherein L _b is any one selected from the group consisting of the same or different structures at each appearance.

The metal complex according to any one of claims 10 to 22, wherein the L _c is any one selected from the group consisting of the same or different structures at each appearance.

The metal complex has a _{Ir (L a) 2 (L} b) or _{Ir (L a) 2 (L} c) or _{Ir (L a) (L c} ) 2 of the structure,
Wherein if the metal complex is having the structure of _{Ir (L a) 2 (L} b), L a is 2 any one or any one selected from the group consisting of _L a1 _{~L a1611} same or different at each occurrence It is a species, and L _b is any one selected from the group consisting of _{L b1 to} L _b322.
Wherein if the metal complex is having the structure of _{Ir (L a) 2 (L} c), L a is 2 any one or any one selected from the group consisting of _L a1 _{~L a1611} same or different at each occurrence It is a species, and L _c is any one selected from the group consisting of _{L c1 to} L _c231.
If the metal complex has a _{Ir (L a) (L c} ) 2 of the structure, _{L a is} any one selected from the group consisting of _{L a1 ~L} a1611, L _c is the same on each occurrence Or differently, any one or two selected from the group consisting of _{L c1 to} L _c231.
The metal complex according to claim 23, wherein the metal complex is preferably selected from the group consisting of compounds 1 to 316.
(The compound 1 Compound 216 and Compound 301 Compound 316 has the structure of _{Ir (L a) 2 (L} b), 2 two _{L a} are the same, and _{L a} and _{L b} correspond respectively Selected from the structures listed in the table below

Compound 217～ compound 300 has the structure of _{Ir (L a) 2 (L} b), different two _{L a,} it is selected from structures mentioned in the following table _{L a} and _{L b} correspond respectively .. )

With the anode
With the cathode
A coutroluminescent device including an organic layer provided between the anode and the cathode.
The organic layer is an electroluminescent device containing the metal complex according to any one of claims 1 to 24. The organic layer is a light emitting layer, and the metal complex is a light emitting material.
Preferably, the electroluminescent device emits red or white light and
More preferably, the light emitting layer further comprises at least one host material.
The at least one host material is benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazolyl, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorenyl. 25. The element of claim 25, comprising at least one chemical group selected from the group consisting of siliconfluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxalin, phenanthrene, azaphenanthrene, and combinations thereof. Formulation of a compound comprising the metal complex according to any one of claims 1 to 24.

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