JP7402548B2 - Organic electroluminescent materials and their devices - Google Patents

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 combination of a metal complex containing an L _a ligand having a structure represented by Formula 1, an electroluminescent device containing the metal complex, and a compound.

Organic electronic devices include organic light-emitting diodes (OLEDs), organic field-effect transistors (O-FETs), organic light-emitting transistors (OLETs), organic photovoltaic cells (OPVs), dye-sensitized solar cells (DSSCs), and organic photodetectors. devices, organic photosensitive devices, organic field effect devices (OFQDs), light emitting electrochemical cells (LECs), organic laser diodes, and organic plasma light emitting devices.

In 1987, Tang and Van Slyke of Eastman Kodak described a bilayer organic electroluminescent material comprising an arylamine hole transport layer and a tris-8-hydroxyquinoline-aluminum layer as the electron transport layer and the emissive layer. The element has been reported (Applied Physics Letters, 1987, 51(12): 913-915). Once a bias is applied to the device, green light is emitted from the device. This invention lays the foundation for the development of modern organic light emitting diodes (OLEDs). Most advanced OLEDs may include multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more emissive layers between the cathode and anode. OLEDs are self-emissive solid-state devices and therefore offer tremendous potential for display and lighting applications. Also, the inherent properties of organic materials, such as their flexibility, make them well suited for special applications such as manufacturing with flexible substrates.

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

OLEDs may be further divided into small molecule and polymer OLEDs, depending on the form of the materials required. Small molecules refer to materials that are not polymers, either organic or organometallic, and the molecular weight of small molecules can be large if they have a precise structure. Dendrimers with well-defined structures are considered small molecules. Polymer OLEDs include a conjugated polymer and a non-conjugated polymer having side chain light-emitting groups. Small molecule OLEDs can become polymeric OLEDs if post-polymerization occurs during the manufacturing process.

Various OLED manufacturing methods 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 manufactured by solution methods if the materials can be dissolved or dispersed in a solvent.

The emitted color of OLED can be realized by the structural design of the light emitting material. OLEDs may include one or more emissive layers to achieve the desired spectrum. Although phosphorescent materials have already been successfully commercialized in green, yellow, and red OLEDs, blue phosphorescent devices still have some drawbacks such as non-saturation of blue color, short service life, and high working voltage. A problem exists. Commercially available full-color OLED displays generally use a mixed strategy, using blue fluorescence and yellow, red or green phosphorescence. Currently, a problem exists that the efficiency of phosphorescent OLEDs decreases rapidly at high brightness. It is also desirable to have a more saturated emission spectrum, higher efficiency, and longer device lifetime.

ただし、Ｘ_１～Ｘ_８のうちの少なくとも１つは、Ｃ－ＣＮから選ばれ、以下のように示される構造を有するイリジウム錯体をさらに開示した。

それは、有機エレクトロルミネッセンス素子に用いられることにより、素子の性能および顔色飽和度を向上させることができ、既に業界の高い水準に達しているが、依然として向上する余地がある。該出願では、Ｒ_４がフェニル基であるアリール基置換基を有する金属錯体および素子における使用のみ開示されており、該金属錯体の特定の位置に本願に係る特定の（ヘテロ）アリール基を導入することが素子の性能に対する影響が開示、教示されていない。 The applicant of the present application disclosed the ligand structure shown below in the previously filed US Patent Application Publication No. 2020/0251666,

However, at least one of X ₁ to X ₈ is selected from C-CN, and an iridium complex having the structure shown below was further disclosed.

It can be used in organic electroluminescent devices to improve the device performance and complexion saturation, which has already reached the high standards of the industry, but there is still room for improvement. This application discloses only a metal complex having an aryl group substituent in which R ₄ is a phenyl group and its use in devices, and the specific (hetero)aryl group according to the present application is introduced at a specific position of the metal complex. However, the effect on the performance of the device is not disclosed or taught.

以下のような構造を有するイリジウム錯体をさらに開示した。

該出願では、配位子の特定の位置におけるフッ素により、素子の耐用年数、熱安定性を含む材料の性能を向上させることができるが、依然として向上する余地がある。該出願では、Ｒ_４がフェニル基であるアリール基置換基を有する金属錯体およびその素子における使用のみ開示されており、該金属錯体の特定の位置に本願に係る特定の（ヘテロ）アリール基を導入することが素子の性能に対する影響が開示、教示されていない。 The applicant of the present application disclosed the following ligand structure in the previously filed US Patent Application Publication No. 2020/0091442,

Further disclosed is an iridium complex having the following structure.

In that application, fluorine at specific positions of the ligand can improve the performance of the material, including device service life, thermal stability, but there is still room for improvement. This application discloses only a metal complex having an aryl substituent in which R ₄ is a phenyl group and its use in a device, and introduces a specific (hetero)aryl group according to the present application into a specific position of the metal complex. The effect of this on the performance of the device is not disclosed or taught.

ただし、Ｒ_１～Ｒ_４は、水素、重水素、アルキル基、シクロアルキル基、アリール基、ヘテロアリール基、およびこれらの組合せから選ばれる。該出願では、Ｒ_１がフェニル基であるアリール基置換基を有する金属錯体およびその素子における使用のみ開示されており、該金属錯体の特定の位置に本願に係る特定の（ヘテロ）アリール基を導入することが素子の性能に対する影響が開示、教示されていない。 US Patent Application Publication No. 2013/119354 discloses a metal complex having a structure represented by the following general formula.

However, R ₁ to R ₄ are selected from hydrogen, deuterium, an alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, and a combination thereof. This application discloses only a metal complex having an aryl substituent in which R ₁ is a phenyl group and its use in a device, and introduces a specific (hetero)aryl group according to the present application into a specific position of the metal complex. The effect of this on the performance of the device is not disclosed or taught.

ただし、Ｘ_１は、シリコン、ゲルマニウムから選ばれ、以下の一般式で表される構造を有するイリジウム錯体がさらに開示されている。

該出願では、主に、金属錯体にシリル基またはゲルマニウム基を導入することが素子の性能に対する影響のみ着目されており、該金属錯体の特定の位置に本願に係る特定の（ヘテロ）アリール基を導入することが素子の性能に対する影響が開示、教示されていない。 US Patent Application Publication No. 2020/0287144 discloses a metal complex containing a ligand structure represented by the following structure,

However, X ₁ is selected from silicon and germanium, and an iridium complex having a structure represented by the following general formula is further disclosed.

In this application, the focus is mainly on the effect of introducing a silyl group or germanium group into a metal complex on the performance of the device, and the specific (hetero)aryl group according to the present application is introduced at a specific position of the metal complex. The effect of the introduction on the performance of the device is not disclosed or taught.

US Patent Application Publication No. 2020/0251666 US Patent Application Publication No. 2020/0091442 US Patent Application Publication No. 2013/119354 US Patent Application Publication No. 2020/0287144

The present invention aims to provide a series of metal complexes containing an L _a ligand having a structure represented by Formula 1, in order to solve at least part of the above-mentioned problems.

（式１中、金属Ｍは、相対原子質量が４０超えの金属から選ばれ、
Ｃｙは、出現毎に同一または異なって置換または非置換の環原子数６～２４の芳香族環、置換または非置換の環原子数５～２４のヘテロ芳香族環、またはこれらの組合せから選ばれ、
Ｘは、Ｏ、Ｓ、Ｓｅ、ＮＲ’、ＳｉＲ’Ｒ’およびＧｅＲ’Ｒ’からなる群から選ばれ、２つのＲ’が同時に存在する場合、２つのＲ’は、同一または異なり、
Ｘ_１～Ｘ_５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、
Ａｒは、式２で表される構造を有し、

ａは、０、１、２、３、４または５から選ばれ、
Ｒ_ａ１およびＲ_ａ２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、
環Ａｒ_１および環Ａｒ_２は、出現毎に同一または異なって環原子数６～３０の芳香族環、環原子数５～３０のヘテロ芳香族環、またはこれらの組合せから選ばれ、且つ環Ａｒ_１および環Ａｒ_２の環原子数の合計が８以上であり、
Ｒ’、Ｒ_ｘ、Ｒ_ａ１およびＲ_ａ２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環原子数３～２０のヘテロ環基、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２～２０のアルキニル基、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３～２０のアルキルゲルマニウム基、置換または非置換の炭素原子数６～２０のアリールゲルマニウム基、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、

は、式２の結合箇所を表し、
隣り合う置換基Ｒ’、Ｒ_ｘ、Ｒ_ａ１、Ｒ_ａ２は、結合して環を形成していてもよい。） According to an embodiment of the present invention, a metal complex including a metal M and a ligand L _a coordinating with the metal M, wherein L _a is a metal complex having a structure represented by Formula 1 is disclosed. be done.

(In formula 1, metal M is selected from metals with a relative atomic mass of more than 40,
Cy is the same or different at each occurrence selected from a substituted or unsubstituted aromatic ring having 6 to 24 ring atoms, a substituted or unsubstituted heteroaromatic ring having 5 to 24 ring atoms, or a combination thereof; ,
X is selected from the group consisting of O, S, Se, NR', SiR'R' and GeR'R', and when two R's are present at the same time, the two R's are the same or different,
X ₁ to X ₅ are the same or different for each occurrence and are selected from CR _x or N;
Ar has a structure represented by formula 2,

a is selected from 0, 1, 2, 3, 4 or 5,
R _a1 and R _a2 are the same or different for each occurrence and represent one substitution, multiple substitutions, or no substitution,
Ring Ar ₁ and ring Ar ₂ are the same or different at each occurrence and are selected from an aromatic ring having 6 to 30 ring atoms, a heteroaromatic ring having 5 to 30 ring atoms, or a combination thereof; ₁ and the total number of ring atoms of ring Ar ₂ is 8 or more,
R', R _x , R _a1 and R _a2 are the same or different at each occurrence and are hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted ring carbon atom Cycloalkyl group having 3 to 20 ring atoms, substituted or unsubstituted heteroalkyl group having 1 to 20 ring atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted 7 carbon atoms ~30 aralkyl group, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms group, substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, 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, substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, substituted or unsubstituted Aryl germanium 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, hydroxy group, sulfanyl group , a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

represents the joining point of formula 2,
Adjacent substituents R', R _x , R _a1 , and R _a2 may be bonded to form a ring. )

According to another embodiment of the invention, there is provided an electroluminescent device comprising an anode, a cathode, and an organic layer provided between the anode and the cathode, the organic layer comprising a metal as described in the above embodiments. Further disclosed are electroluminescent devices comprising the complex.

According to other embodiments of the invention, combinations of compounds comprising the metal complexes described in the above embodiments are further disclosed.

The present invention discloses a series of metal complexes containing L _a ligands having the structure represented by formula 1. The metal complex can be used as a light emitting material in an electroluminescent device. When used in electroluminescent devices, these new compounds can exhibit better performance, lower driving voltage, and improve device efficiency, especially EQE, and finally clarify the overall performance of devices. can be improved.

1 is a schematic diagram of an organic light-emitting device that may include a combination of metal complexes and compounds according to the invention; FIG. FIG. 2 is a schematic diagram of another organic light emitting device that may include a combination of metal complexes and compounds according to the present invention.

OLEDs can be manufactured with a variety of substrates such as glass, plastic, and metal. FIG. 1 shows an illustrative and non-limiting organic light emitting device 100. The drawings are not necessarily drawn to scale, and some layered structures may be omitted from the drawings if necessary. The device 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. Device 100 may be manufactured by depositing the described layers in sequence. The nature, function and exemplary materials of each layer are described in more detail in US Pat. No. 7,279,704 B2, columns 6-10, the entire contents of which are incorporated herein by reference.

There are many more examples of each of these layers. Illustratively, a flexible transparent substrate-anode combination is disclosed in US Pat. No. 5,844,363, which is incorporated by reference in its entirety. For example, in _US Pat. It is disclosed that MTDATA. Examples of host materials are disclosed in US Pat. No. 6,303,238 to Thompson et al., which is incorporated by reference in its entirety. For example, in U.S. Patent Application Publication No. 2003/0230980, which is incorporated by reference in its entirety, an example of an n-type doped electron transport layer is disclosed to be BPhen doped with Li in a 1:1 molar ratio. has been done. No. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, have a thin metal layer, e.g. Examples of cathodes, including composite cathodes, are disclosed. The principles and use of blocking layers are described in more detail in US Patent No. 6,097,147 and US Patent Application Publication No. 2003/0230980, which are incorporated by reference in their entirety. An example of an injection layer is provided in US Patent Application Publication No. 2004/0174116, which is incorporated by reference in its entirety. Protective layers are described in US Patent Application Publication No. 2004/0174116, which is incorporated by reference in its entirety.

A non-limiting example provides a split layer structure as described above. OLED functionality can be realized by combining the various layers described above, or some layers can be omitted completely. It may contain other layers not explicitly mentioned. A single material or a mixture of materials can be used within each layer to achieve optimal performance. Any functional layer may include multiple sublayers; for example, a light-emitting layer may have two layers of different light-emitting materials to achieve a desired emission spectrum.

In one example, an OLED may be described as having an "organic layer" disposed between a cathode and an anode. The organic layer may include one or more layers.

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

Devices manufactured according to embodiments of the present invention may be incorporated into various consumer products having one or more electronic component modules (or units) of the device. These consumer products include, for example, flat panel displays, monitors, medical monitors, televisions, billboards, indoor or outdoor lighting and/or signal lamps, heads-up displays, fully or partially transparent displays, flexible Including displays, smartphones, flat panel computers, flat panel mobile phones, wearable devices, smart watches, laptop computers, digital cameras, handheld video cameras, viewfinders, micro displays, 3-D displays, in-vehicle displays and tail lights.

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

"Top" means furthest from the substrate and "bottom" means closest from the substrate. When a first layer is described as being disposed "on" a second layer, it is meant that the first layer is disposed relatively far from the substrate. Other layers may be present between the first and second layers, unless it is specified that the first layer is in "contact" with the second layer. Illustratively, the cathode can still be described as being provided "on" the anode, even though various organic layers are present between the cathode and the anode.

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

It is believed that a ligand may be referred to as "photosensitive" if it directly promotes the photosensitive properties of the launch material. A ligand may be termed "auxiliary" if it does not promote the photosensitive properties of the launch material. However, it is believed that auxiliary ligands can modify the properties of the photosensitive ligand.

It is believed that the internal quantum efficiency (IQE) of fluorescent OLEDs may exceed the 25% spin statistical limit due to the presence of delayed fluorescence. Delayed fluorescence may be generally divided into two types: P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).

On the other hand, E-type delayed fluorescence depends on the excited state conversion between a triplet and a singlet rather than the collision of two triplets. Compounds capable of producing E-type delayed fluorescence need to have an extremely small singlet-triplet gap so as to effect a conversion of energy states. Thermal energy can activate the triplet to singlet transition. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). A distinctive feature of TADF is that the retardation component improves with increasing temperature. If the rate of penetration (reverse intersystem crossing) between the reverse systems (RISC) is fast enough, the non-radiative attenuation from the triplet can be minimized, and the fraction of excited states in the backfilled singlet can reach 75%. Can be done. The total fraction of singlets may be 100%, which is much more than 25% of the electroexciton spin statistics.

The E-type delayed fluorescence signature is visible from an excited complex system or a single compound. Without being limited by theory, E-type delayed fluorescence requires that the emissive material has a small singlet-triplet energy gap (ΔE _ST ). Organo-nonmetal-containing donor-acceptor emissive materials have the potential to accomplish this. The launch of these materials is typically characterized as donor-acceptor charge transition (CT) type launch. In these donor-acceptor type compounds, the spatial separation of the HOMO and LUMO will generally produce a small ΔE _ST . These conditions may include CT conditions. Typically, donor-acceptor luminescent materials are constructed by linking an electron donor moiety (eg, an amine group or a carbazole derivative) and an electron acceptor moiety (eg, an N-containing six-membered aromatic ring).

Definitions of terminology for substituents

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

Alkyl group, as used herein, includes straight chain and branched chain alkyl groups. The alkyl group may be an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 12 carbon atoms, and more preferably an alkyl group having 1 to 6 carbon atoms. Examples of alkyl groups 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-butylpentyl, 1-heptyloctyl, and 3-methylpentyl. Among them, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl and n-hexane are preferred. Moreover, the alkyl group may be substituted.

Cycloalkyl group, as used herein, includes cyclic alkyl groups. The cycloalkyl group may be a cycloalkyl group having 3 to 20 ring carbon atoms, preferably a cycloalkyl group having 4 to 10 ring carbon atoms. Examples of cycloalkyl groups include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, and the like. Among them, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, and 4,4-dimethylcyclohexyl are preferred. Moreover, the cycloalkyl group may be substituted.

As used herein, a heteroalkyl group refers to a group in which one or more carbons in the alkyl chain is a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a phosphorous atom, a silicon atom, a germanium atom, and a boron atom. substituted with a heteroatom selected from the group consisting of atoms. 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 preferably a heteroalkyl group having 1 to 6 carbon atoms. is more preferable. Examples of heteroalkyl groups are methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl group, hydroxyethyl group, hydroxypropyl group, mercaptomethyl group, mercaptoethyl group, mercaptopropyl group, aminomethyl group, aminoethyl group, aminopropyl group, dimethylaminomethyl group, trimethylgermaniummethyl group, trimethylgermaniumethyl group, trimethyl Germanium isopropyl group, dimethylethylgermanium methyl group, dimethylisopropylgermanium methyl group, tert-butyldimethylgermanium methyl group, triethylgermanium methyl group, triethylgermanium ethyl group, triisopropylgermanium methyl group, triisopropylgermanium ethyl group, trimethylsilylmethyl group, Trimethylsilylisopropyl group, trimethylsilylisopropyl group, triisopropylsilylmethyl group, triisoprooylsilylethyl group. Moreover, a heteroalkyl group may be substituted.

Alkenyl groups, as used herein, include straight chain, branched chain and cyclic olefin groups. 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 vinyl, propylene, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl. , 1,2-diphenylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group, 1-phenylallyl group, 2-phenylallyl group, 3-phenylallyl group, 3,3-diphenyl Allyl group, 1,2-dimethylallyl group, 1-phenyl-1-butenyl group, 3-phenyl-1-butenyl group, cyclopentenyl group, cyclopentadienyl group, cyclohexenyl group, cycloheptenyl group, cycloheptatrienyl group cyclooctenyl, cyclooctatetraenyl and norbornylalkenyl groups. Moreover, an alkenyl group may be substituted.

Alkynyl group, as used herein, includes straight chain alkynyl groups. 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-1-pentynyl group, 3,3-diisopropyl-1-pentynyl group, phenylethynyl group, phenylpropynyl group, and the like. Among these, ethynyl group, propynyl group, propargyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-pentynyl group, and phenylethynyl group are preferable. Moreover, an alkynyl group may be substituted.

Aryl or aromatic group, as used herein, contemplates non-fused and fused systems. The aryl group may be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene; Preferably it is naphthalene. Examples of non-fused aryl groups are phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-tribiphenyl. -2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl) phenyl, 4'-methylbiphenyl, 4''-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylyl, 3,4-xylyl , 2,5-dimethylphenyl, mesitylene and m-tetraphenyl. Moreover, the aryl group may be substituted.

Heterocyclic group or heterocycle, as used herein, contemplates a non-aromatic cyclic group. Non-aromatic heterocyclic groups include saturated heterocyclic groups having 3 to 20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3 to 20 ring atoms, at least one ring atom of which is a nitrogen atom, The non-aromatic heterocyclic group is preferably selected from the group consisting of oxygen atom, sulfur atom, selenium atom, silicon atom, phosphorus atom, germanium atom and boron atom, and has 3 to 7 ring atoms, and nitrogen , at least one heteroatom such as oxygen, silicon or sulfur. Examples of non-aromatic heterocyclic groups are oxiranyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxopentyl, dioxanyl, aziridinyl, dihydropyrrole, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxacycloheptatrienyl, Includes thiacycloheptatrienyl, azacycloheptatrienyl and tetrahydrosilole. Moreover, the heterocyclic group may be substituted.

Heteroaryl groups, as used herein, may include non-fused and fused heteroaromatic groups having from 1 to 5 heteroatoms, at least one of which is a nitrogen atom, an oxygen atom, selected from the group consisting of sulfur atom, selenium atom, silicon atom, phosphorus atom, germanium atom and boron atom. An 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 preferably 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, pyridindole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, Thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indenoazine, benzoxazole, benzisoxazole, benzothiazole, quinoline , isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzofuranpyridine, frangipyridine, benzothienopyridine, thienobipyridine, benzoselenopyridine, and selenium benzopyridine, dibenzothiophene, dibenzofuran , dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborane, 1,3-azaborane, 1,4-azaborane, borazole and aza analogs thereof. Moreover, a heteroaryl group may be substituted.

As used herein, the alkoxy group is represented by an -O-alkyl group, -O-cycloalkyl group, -O-heteroalkyl group or -O-heterocyclic group. Examples and preferred examples of the alkyl group, cycloalkyl group, heteroalkyl group and heterocyclic group are the same as the above examples. 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 are methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy , methoxymethyloxy and ethoxymethyloxy. Moreover, the alkoxy group may be substituted.

As used herein, the aryloxy group is represented by an -O-aryl group or an -O-heteroaryl group. Examples and preferred examples of the aryl group and heteroaryl group are the same as the above examples. 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. Furthermore, the aryloxy group may be substituted.

Aralkyl groups, as used herein, include alkyl groups substituted with aryl groups. 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- Naphthyl ethyl, 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. Among them, benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl and 2-phenylisopropyl are preferred. Furthermore, the aralkyl group may be substituted.

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

Arylsilyl groups, as used herein, include silyl groups substituted with at least one aryl group. The arylsilyl group may be an arylsilyl group having 6 to 30 carbon atoms, and is preferably an arylsilyl group having 8 to 20 carbon atoms. Examples of arylsilyl groups are triphenylsilyl, phenyldiviphenylsilyl, diphenylbiphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutyl silyl, diphenyl-tert-butylsilyl. Furthermore, the arylsilyl group may be substituted.

As used herein, an alkylgermanium group includes a germanium group substituted with an alkyl group. The alkylgermanium group may be an alkylgermanium group having 3 to 20 carbon atoms, and is preferably an alkylgermanium group having 3 to 10 carbon atoms. Examples of alkylgermanium groups are trimethylgermanium group, triethylgermanium group, methyldiethylgermanium group, ethyldimethylgermanium group, tripropylgermanium group, tributylgermanium group, triisopropylgermanium group, methyldiisopropylgermanium group, dimethylisopropylgermanium group, -tert-butylgermanium group, triisobutylgermanium group, dimethyl-tert-butylgermanium group, and methyldi-tert-butylgermanium group. Further, the alkylgermanium group may be substituted.

Arylgermanium groups, as used herein, include germanium groups substituted with at least one aryl or heteroaryl group. The aryl germanium group may be an aryl germanium group having 6 to 30 carbon atoms, and is preferably an aryl germanium group having 8 to 20 carbon atoms. Examples of arylgermanium groups are triphenylgermanium group, phenyldibiphenylgermanium group, diphenylbiphenylgermanium group, phenyldiethylgermanium group, diphenylethylgermanium group, phenyldimethylgermanium group, diphenylmethylgermanium group, phenyldiisopropylgermanium group, diphenylisopropyl group. It includes a germanium group, a diphenylbutylgermanium group, a diphenylisobutylgermanium group, and a diphenyl-tert-butylgermanium group. Moreover, the aryl germanium group may be substituted.

“Aza” in azadibenzofuran, azadibenzothiophene, etc. refers to the substitution of one or more C—H groups in the corresponding aromatic fragment with a nitrogen atom. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline, and other analogs having two or more nitrogens in the ring system. Those skilled in the art can readily envision other nitrogen analogs of the above-mentioned aza derivatives, and all such analogs are determined to be included within 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 heterocyclic group, a substituted aralkyl group, a substituted alkoxy group, a substituted aryloxy group, a substituted alkenyl group, substituted alkynyl group, substituted aryl group, substituted heteroaryl group, substituted alkylsilyl group, substituted arylsilyl group, substituted alkylgermanium group, substituted arylgermanium group, substituted amino group, substituted An alkyl group, Cycloalkyl group, heteroalkyl group, heterocyclyl group, aralkyl group, alkoxy group, aryloxy group, alkenyl group, alkynyl, aryl group, heteroaryl group, alkylsilyl group, arylsilyl group, alkylgermanium group, arylgermanium group, amino group, acyl group, carbonyl group, carboxyl group, ester group, sulfinyl group, sulfonyl group, and phosphino group is deuterium, halogen, or an unsubstituted alkyl group having 1 to 20 carbon atoms. , an unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, an unsubstituted heteroalkyl group having 1 to 20 ring atoms, an unsubstituted heterocyclic group having 3 to 20 ring atoms, an unsubstituted heterocyclic group having 3 to 20 ring atoms; aralkyl group having 7 to 30 carbon atoms, unsubstituted alkoxy group having 1 to 20 carbon atoms, unsubstituted aryloxy group having 6 to 30 carbon atoms, unsubstituted alkenyl group having 2 to 20 carbon atoms, unsubstituted Alkynyl group having 2 to 20 carbon atoms, unsubstituted aryl group having 6 to 30 carbon atoms, unsubstituted heteroaryl group having 3 to 30 carbon atoms, unsubstituted alkylsilyl group having 3 to 20 carbon atoms , unsubstituted arylsilyl group having 6 to 20 carbon atoms, unsubstituted alkylgermanium group having 3 to 20 carbon atoms, unsubstituted arylgermanium group having 6 to 20 carbon atoms, unsubstituted 0 carbon atoms by one or more selected from ~20 amino groups, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof It means that it can be replaced.

When a molecular fragment is described as attached to another moiety by a substituent or other form, it refers to whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or the entire molecule. It should be understood that the name can be determined depending on whether it is a compound (eg, benzene, naphthalene, dibenzofuran). As used herein, different forms of substituent designation or fragment attachment are considered equivalent.

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

In the compounds referred to herein, multiple substitution refers to the range up to the most available substitutions, including double substitutions. A substituent in a compound referred to herein means multiple substitutions (including double, triple, quadruple, etc.), meaning that the substituent has multiple available substitutions on its bonding structure. This means that the substituents may be present at a substituent position, and the substituents present at any of a plurality of available substituent positions may have the same structure or may have different structures.

In the compounds mentioned herein, adjacent substituents in the compound may not be combined to form a ring, unless otherwise specified. Can not. In the compounds referred to in this specification, the fact that adjacent substituents may combine to form a ring does not only include situations where adjacent substituents may combine to form a ring. , including situations where adjacent substituents do not combine to form a ring. When adjacent substituents may combine to form a ring, the ring formed may be a monocyclic or polycyclic ring, and an alicyclic, heteroalicyclic, aryl, or heteroaryl ring. . In such descriptions, adjacent substituents refer to substituents that are bonded to the same atom, substituents that are bonded to carbon atoms that are directly bonded to each other, or substituents that are bonded to carbon atoms that are further apart. Good too. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms that are directly bonded to each other.

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

The statement that adjacent substituents may bond to form a ring also means that two substituents bonded to carbon atoms that are directly bonded to each other bond to each other through a chemical bond to form a ring. It is recognized and can be exemplified by the following formula.

The statement that adjacent substituents may be bonded to form a ring is also accepted to mean that two substituents bonded to carbon atoms that are further apart are bonded to each other through a chemical bond to form a ring. , can be exemplified by the following formula.

Furthermore, the statement that adjacent substituents may be bonded together to form a ring also applies when one of two substituents bonded to carbon atoms that are directly bonded to each other represents hydrogen, and the second substituent It is accepted to mean that a hydrogen atom is attached at the point where it is attached to form a ring. The following formula is used as an example.

（式１中、金属Ｍは、相対原子質量が４０超えの金属から選ばれ、
Ｃｙは、出現毎に同一または異なって置換または非置換の環原子数６～２４の芳香族環、置換または非置換の環原子数５～２４のヘテロ芳香族環、またはこれらの組合せから選ばれ、
Ｘは、Ｏ、Ｓ、Ｓｅ、ＮＲ’、ＳｉＲ’Ｒ’およびＧｅＲ’Ｒ’からなる群から選ばれ、２つのＲ’が同時に存在する場合、２つのＲ’は、同一または異なり、
Ｘ_１～Ｘ_５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、
Ａｒは、式２で表される構造を有し、

ａは、０、１、２、３、４または５から選ばれ、
Ｒ_ａ１およびＲ_ａ２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、
環Ａｒ_１および環Ａｒ_２は、出現毎に同一または異なって環原子数６～３０の芳香族環、環原子数５～３０のヘテロ芳香族環、またはこれらの組合せから選ばれ、且つ環Ａｒ_１および環Ａｒ_２の環原子数の合計が８以上であり、
Ｒ’、Ｒ_ｘ、Ｒ_ａ１およびＲ_ａ２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環原子数３～２０のヘテロ環基、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２～２０のアルキニル基、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３～２０のアルキルゲルマニウム基、置換または非置換の炭素原子数６～２０のアリールゲルマニウム基、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、

は、式２の結合箇所を表し、
隣り合う置換基Ｒ’、Ｒ_ｘ、Ｒ_ａ１、Ｒ_ａ２は、結合して環を形成していてもよい。） According to an embodiment of the present invention, a metal complex including a metal M and a ligand L _a coordinating with the metal M, wherein L _a is a metal complex having a structure represented by Formula 1 is disclosed. be done.

(In formula 1, metal M is selected from metals with a relative atomic mass of more than 40,
Cy is the same or different at each occurrence selected from a substituted or unsubstituted aromatic ring having 6 to 24 ring atoms, a substituted or unsubstituted heteroaromatic ring having 5 to 24 ring atoms, or a combination thereof; ,
X is selected from the group consisting of O, S, Se, NR', SiR'R' and GeR'R', and when two R's are present at the same time, the two R's are the same or different,
X ₁ to X ₅ are the same or different for each occurrence and are selected from CR _x or N;
Ar has a structure represented by formula 2,

a is selected from 0, 1, 2, 3, 4 or 5,
R _a1 and R _a2 are the same or different for each occurrence and represent one substitution, multiple substitutions, or no substitution,
Ring Ar ₁ and ring Ar ₂ are the same or different at each occurrence and are selected from an aromatic ring having 6 to 30 ring atoms, a heteroaromatic ring having 5 to 30 ring atoms, or a combination thereof; ₁ and the total number of ring atoms of ring Ar ₂ is 8 or more,
R', R _x , R _a1 and R _a2 are the same or different at each occurrence and are hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted ring carbon atom Cycloalkyl group having 3 to 20 ring atoms, substituted or unsubstituted heteroalkyl group having 1 to 20 ring atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted 7 carbon atoms ~30 aralkyl group, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms group, substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, 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, substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, substituted or unsubstituted Aryl germanium 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, hydroxy group, sulfanyl group , a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

represents the joining point of formula 2,
Adjacent substituents R', R _x , R _a1 , and R _a2 may be bonded to form a ring. )

In _{this specification, "adjacent substituents R′ , R ' , two substituents R} This means that it may be formed. Obviously, none of these substituents need be linked together to form a ring.

で表される構造を有することを示す。その際に、「環Ａｒ_１および環Ａｒ_２の環原子数の合計が８以上である」とは、環Ａｒ_１が環原子数の合計が８以上の芳香族環またはヘテロ芳香族環であることを示す。式２におけるａが１である場合、Ａｒが

で表される構造を有することを示す。例えば、その際に、環Ａｒ_１および環Ａｒ_２がいずれもフェニル基であり、Ｒ_ａ１およびＲ_ａ２がいずれも水素である場合、環Ａｒ_１および環Ａｒ_２の環原子数の合計が１２であり、また、例えば、その際に、環Ａｒ_１および環Ａｒ_２がいずれもフェニル基であり、Ｒ_ａ１がいずれも水素であり、Ｒ_ａ２が一置換であり、且つフェニル基である場合、環Ａｒ_１および環Ａｒ_２の環原子数の合計が１２である。他の状況は、これによって類推する。 In the present specification, a "ring atom" in an aromatic ring and a heteroaromatic ring refers to a cyclic structure in which atoms are bonded to each other to have aromatic properties (e.g., a single-ring (hetero)aromatic ring, a fused ring (hetero) ) aromatic ring) which constitutes the ring itself. All carbon atoms and heteroatoms in the ring (including, but not limited to, O, S, N, Se or Si, etc.) are counted in the number of ring atoms. When the ring is substituted with a substituent, the atoms contained in the substituent are not counted in the number of ring atoms. For example, the number of ring atoms of a phenyl group, a pyridyl group, and a triazine group is six. The number of ring atoms in the fused bithiophene and fused bifuran is 8. Both the benzothienyl group and the benzofuran group have 9 ring atoms. The number of ring atoms in each of the naphthyl group, quinolyl group, isoquinolyl group, quinolidinyl group, and quinoxaline group is 10. Dibenzothiophene, dibenzofuran, fluorene, azadibenzothiophene, azadibenzofuran and azafluorene all have 13 ring atoms. The various examples described herein are merely illustrative, and other situations may be inferred hereby. When a in equation 2 is 0, Ar is

Indicates that it has the structure represented by . In this case, "the total number of ring atoms of ring Ar ₁ and ring Ar ₂ is 8 or more" means that ring Ar ₁ is an aromatic ring or a heteroaromatic ring with a total number of ring atoms of 8 or more. Show that. When a in formula 2 is 1, Ar is

Indicates that it has the structure represented by . For example, in that case, if ring Ar ₁ and ring Ar ₂ are both phenyl groups, and R _a1 and R _a2 are both hydrogen, the total number of ring atoms of ring Ar ₁ and ring Ar ₂ is 12. Also, for example, in that case, when ring Ar ₁ and ring Ar ₂ are both phenyl groups, R _a1 are both hydrogen, and R _a2 is monosubstituted and is a phenyl group, The total number of ring atoms of Ar ₁ and ring Ar ₂ is 12. Other situations are analogous to this.

（Ｒ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、いずれか１つの構造において複数のＲが存在する場合、前記Ｒは、同一または異なり、
Ｒ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環原子数３～２０のヘテロ環基、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２～２０のアルキニル基、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３～２０のアルキルゲルマニウム基、置換または非置換の炭素原子数６～２０のアリールゲルマニウム基、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は、結合して環を形成していてもよく、
「＃」は、金属Ｍとの結合箇所を表し、

は、Ｘ_１、Ｘ_２、Ｘ_３またはＸ_４との結合箇所を表す。） According to one embodiment of the invention, Cy is any one structure selected from the group consisting of the following structures.

(R is the same or different for each occurrence and represents one substitution, multiple substitutions, or no substitution, and when a plurality of R exists in any one structure, the R is the same or different,
R is the same or different at each occurrence, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 ring carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl group having 7 to 30 ring atoms, substituted or unsubstituted an 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 having 2 to 20 carbon atoms; Alkynyl group having 2 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms Alkylsilyl group, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium having 6 to 20 carbon atoms group, substituted or unsubstituted amine group having 0 to 20 carbon atoms, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxy group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof,
Adjacent substituents R may be combined to form a ring,
"#" represents the bonding point with metal M,

represents a bonding site with X ₁ , X ₂ , X ₃ or X ₄ . )

In this specification, "adjacent substituents R may combine to form a ring" means that any one of the substituent groups consisting of any two adjacent substituents R It means that one or more may be combined to form a ring. Obviously, none of these substituents need be linked together to form a ring.

Ｘは、Ｏ、Ｓ、Ｓｅ、ＮＲ’、ＳｉＲ’Ｒ’およびＧｅＲ’Ｒ’からなる群から選ばれ、２つのＲ’が同時に存在する場合、２つのＲ’は、同一または異なり、
Ａｒは、式２で表される構造を有し、

ａは、０、１、２、３、４または５から選ばれ、
環Ａｒ_１および環Ａｒ_２は、出現毎に同一または異なって環原子数６～３０の芳香族環、環原子数５～３０のヘテロ芳香族環、またはこれらの組合せから選ばれ、且つ環Ａｒ_１および環Ａｒ_２の環原子数の合計が８以上であり、
Ｒ、Ｒ_ｘ、Ｒ_ａ１およびＲ_ａ２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、
Ｒ、Ｒ’、Ｒ_ｘ、Ｒ_ａ１およびＲ_ａ２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環原子数３～２０のヘテロ環基、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２～２０のアルキニル基、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３～２０のアルキルゲルマニウム基、置換または非置換の炭素原子数６～２０のアリールゲルマニウム基、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、Ｒ’、Ｒ_ｘ、Ｒ_ａ１およびＲ_ａ２は、結合して環を形成していてもよく、

は、式２の結合箇所を表す。 According to an embodiment of the invention, L _a is selected from the group consisting of the following structures, which are the same or different at each occurrence:

X is selected from the group consisting of O, S, Se, NR', SiR'R' and GeR'R', and when two R's are present at the same time, the two R's are the same or different,
Ar has a structure represented by formula 2,

a is selected from 0, 1, 2, 3, 4 or 5,
Ring Ar ₁ and ring Ar ₂ are the same or different at each occurrence and are selected from an aromatic ring having 6 to 30 ring atoms, a heteroaromatic ring having 5 to 30 ring atoms, or a combination thereof; ₁ and the total number of ring atoms of ring Ar ₂ is 8 or more,
R, R _x , R _a1 and R _a2 are the same or different for each occurrence and represent one substitution, multiple substitutions or no substitution,
R, R', R _x , R _a1 and R _a2 are the same or different at each occurrence, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted ring Cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted heteroalkyl group having 1 to 20 ring atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted carbon atom Aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted 2 to 20 carbon atoms alkenyl group, substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, 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, substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, substituted or Unsubstituted aryl germanium 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, hydroxy group, selected from the group consisting of sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof,
Adjacent substituents R, R', R _x , R _a1 and R _a2 may be combined to form a ring,

represents the connection point in Equation 2.

In this specification, "adjacent substituents R, _{R '} , _R Any one of groups R together, two substituents R′ together, two substituents R _x together, two substituents R _a1 together, two substituents R _a2 together, and substituents R _a1 and R _a2 together This means that one or more may be combined to form a ring. Obviously, none of these substituents need be linked together to form a ring.

からなる群のうちのいずれか１種で表される構造から選ばれ、
Ｒ_ａ、Ｒ_ｂ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、ＣＲ_Ｃ１Ｒ_Ｃ２からなる群から選ばれ、
Ｒ_ａ、Ｒ_ｂ、Ｒ_ｃ、Ｒ_Ｎ１、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環原子数３～２０のヘテロ環基、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２～２０のアルキニル基、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３～２０のアルキルゲルマニウム基、置換または非置換の炭素原子数６～２０のアリールゲルマニウム基、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_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 invention, the metal complex has the general formula M(L _a ) _m (L _b ) _n (L _c ) _q .
(M is the same or different on each occurrence selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt, preferably M is the same or different on each occurrence of Pt or Selected from Ir.
L _a , L _b and L _c are the first, second and third ligands that coordinate with the metal M, respectively, and L _c and the L _a or L _b are the same or different, and L _a , L _b and L _c may be combined to form a polydentate ligand,
m is selected from 1, 2 or 3, n is selected from 0, 1 or 2, q is selected from 0, 1 or 2, m+n+q is equal to the oxidation state of the metal M, and m is 2 or more, the plural L _a 's are the same or different; when n is 2, the two L _b 's are the same or different; when q is 2, the two L _c 's are the same or different;
L _b and L _c are the same or different for each occurrence

selected from the structures represented by any one of the group consisting of,
R _a and R _b are the same or different for each occurrence and represent one substitution, multiple substitutions, or no substitution,
X _b is the same or different for each occurrence and is selected from the group consisting of O, S, Se, NR _N1 , CR _C1 R _C2 ,
R _a , R _b , R _c , R _N1 , R _C1 and R _C2 are the same or different at each occurrence and represent hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring atoms; substituted or unsubstituted heteroalkyl group having 1 to 20 ring atoms; substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms; Substituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted carbon atom Alkenyl group having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted aryl group having 3 to 30 carbon atoms Heteroaryl group, substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms group, substituted or unsubstituted aryl germanium 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 , a hydroxy group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
Adjacent substituents R _a , R _b , R _c , R _N1 , R _C1 and R _C2 may be combined to form a ring. )

In this specification, "adjacent substituents R _a , R _b , R _c , R _N1 , R _C1 and R _C2 may be bonded to form a ring" means that adjacent substituent groups, e.g. , two substituents R _a together, two substituents R _b together, two substituents R c together, substituents R _a and R _b together, substituents R _a and R _c together, substituents R _b and _{R c} substituents R _a and R _N1 together, substituents R _b and R N1 together, substituents R _a and R _C1 together, substituents R _a and R _C2 together, substituents R _b and R _C1 together, substituent _R It means that any one or more of _b and R _C2 and R _C1 and R _C2 may be bonded to each other to form a ring. Obviously, none of these substituents need be linked together to form a ring.

According to one embodiment of the invention, the metal M is selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt, the same or different on each occurrence.

According to one embodiment of the invention, the metal M is chosen from Pt or Ir, the same or different in each occurrence.

（Ｘは、Ｏ、Ｓ、Ｓｅ、ＮＲ’、ＳｉＲ’Ｒ’およびＧｅＲ’Ｒ’からなる群から選ばれ、２つのＲ’が同時に存在する場合、２つのＲ’は、同一または異なり、
ｍは、１、２または３から選ばれ、ｍが１から選ばれる場合、２つのＬ_ｂは、同一または異なり、ｍが２または３から選ばれる場合、複数のＬ_ａは、同一または異なり、
Ｙ_１～Ｙ_４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、
Ｘ_１～Ｘ_５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、
Ａｒは、式２で表される構造を有し、

ａは、０、１、２、３、４または５から選ばれ、
Ｒ_ａ１およびＲ_ａ２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、
環Ａｒ_１および環Ａｒ_２は、出現毎に同一または異なって環原子数６～３０の芳香族環、環原子数５～３０のヘテロ芳香族環、またはこれらの組合せから選ばれ、且つ環Ａｒ_１および環Ａｒ_２の環原子数の合計が８以上であり、

は、式２の結合箇所を表し、
Ｒ’、Ｒ_ｘ、Ｒ_ｙ、Ｒ_１～Ｒ_８、Ｒ_ａ１およびＲ_ａ２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環原子数３～２０のヘテロ環基、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２～２０のアルキニル基、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３～２０のアルキルゲルマニウム基、置換または非置換の炭素原子数６～２０のアリールゲルマニウム基、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’、Ｒ_ｘ、Ｒ_ｙ、Ｒ_ａ１、Ｒ_ａ２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_８は、結合して環を形成していてもよい。） According to one embodiment of the invention, the metal complex Ir(L _a ) _m (L _b ) _3-m has a structure represented by formula 3.

(X is selected from the group consisting of O, S, Se, NR', SiR'R' and GeR'R', and when two R's are present at the same time, the two R's are the same or different,
m is selected from 1, 2 or 3; when m is selected from 1, the two L _b 's are the same or different; when m is selected from 2 or 3, the plural L _a 's are the same or different;
Y ₁ to Y ₄ are the same or different for each occurrence and are selected from CR _y or N,
X ₁ to X ₅ are the same or different for each occurrence and are selected from CR _x or N;
Ar has a structure represented by formula 2,

a is selected from 0, 1, 2, 3, 4 or 5,
R _a1 and R _a2 are the same or different for each occurrence and represent one substitution, multiple substitutions, or no substitution,
Ring Ar ₁ and ring Ar ₂ are the same or different at each occurrence and are selected from an aromatic ring having 6 to 30 ring atoms, a heteroaromatic ring having 5 to 30 ring atoms, or a combination thereof; ₁ and the total number of ring atoms of ring Ar ₂ is 8 or more,

represents the joining point of formula 2,
R', R _x , R _y , R ₁ to R ₈ , R _a1 and R _a2 are the same or different at each occurrence and represent hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; , a substituted or unsubstituted cycloalkyl group having 3 to 20 ring atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 ring atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring 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 unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted Alkenyl group having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted 3 carbon atoms ~30 heteroaryl group, substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted 3 to 20 carbon atoms alkyl germanium group, substituted or unsubstituted aryl germanium 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, hydroxy group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof,
Adjacent substituents R', R _x , R _y , R _a1 , and R _a2 may be combined to form a ring,
Adjacent substituents R ₁ to R ₈ may be bonded to form a ring. )

In this specification, "adjacent substituents R', R _x , R _y , R _a1 , and R _a2 may be bonded to form a ring" means that adjacent substituent groups, for example, two Substituents R′ together, two substituents R _x together, two substituents R _y together, two substituents R _a1 together, two substituents R _a2 together, two substituents R _a1 and R _a2 together, 2 It means that any one or more of the two substituents R' and R _x may be bonded to each other to form a ring. Obviously, none of these substituents need be linked together to form a ring. "Adjacent substituents R ₁ to R ₈ may combine to form a ring" means adjacent substituent groups, for example, adjacent substituents R ₁ and R ₂ , adjacent substituents R ₃ and R ₂ together, adjacent substituents R ₃ and R ₄ together, adjacent substituents R ₅ and R ₄ together, adjacent substituents R ₅ and R ₆ together, adjacent substituents R ₇ and R ₆ together, This means that any one or more of the adjacent substituents R ₇ and R ₈ may be bonded to each other to form a ring. Obviously, none of these substituents need be linked together to form a ring.

（Ｘは、Ｏ、Ｓ、Ｓｅ、ＮＲ’、ＳｉＲ’Ｒ’およびＧｅＲ’Ｒ’からなる群から選ばれ、２つのＲ’が同時に存在する場合、２つのＲ’は、同一または異なり、
ｍは、１、２または３から選ばれ、ｍが１から選ばれる場合、２つのＬ_ｂは、同一または異なり、ｍが２または３から選ばれる場合、複数のＬ_ａは、同一または異なり、
Ｒ_ｘおよびＲ_ｙ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、
Ａｒは、式２で表される構造を有し、

ａは、０、１、２、３、４または５から選ばれ、
Ｒ_ａ１およびＲ_ａ２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、
環Ａｒ_１および環Ａｒ_２は、出現毎に同一または異なって環原子数６～３０の芳香族環、環原子数５～３０のヘテロ芳香族環、またはこれらの組合せから選ばれ、且つ環Ａｒ_１および環Ａｒ_２の環原子数の合計が８以上であり、

は、式２の結合箇所を表し、
Ｒ’、Ｒ_ｘ、Ｒ_ｙ、Ｒ_１～Ｒ_８、Ｒ_ａ１およびＲ_ａ２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環原子数３～２０のヘテロ環基、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２～２０のアルキニル基、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３～２０のアルキルゲルマニウム基、置換または非置換の炭素原子数６～２０のアリールゲルマニウム基、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’、Ｒ_ｘ、Ｒ_ｙ、Ｒ_ａ１、Ｒ_ａ２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_８は、結合して環を形成していてもよい。） According to one embodiment of the invention, the metal complex Ir(L _a ) _m (L _b ) _3-m has a structure represented by formula 3A.

(X is selected from the group consisting of O, S, Se, NR', SiR'R' and GeR'R', and when two R's are present at the same time, the two R's are the same or different,
m is selected from 1, 2 or 3; when m is selected from 1, the two L _b 's are the same or different; when m is selected from 2 or 3, the plural L _a 's are the same or different;
R _x and R _y are the same or different for each occurrence and represent one substitution, multiple substitutions, or no substitution,
Ar has a structure represented by formula 2,

a is selected from 0, 1, 2, 3, 4 or 5,
R _a1 and R _a2 are the same or different for each occurrence and represent one substitution, multiple substitutions, or no substitution,
Ring Ar ₁ and ring Ar ₂ are the same or different at each occurrence and are selected from an aromatic ring having 6 to 30 ring atoms, a heteroaromatic ring having 5 to 30 ring atoms, or a combination thereof; ₁ and the total number of ring atoms of ring Ar ₂ is 8 or more,

represents the joining point of formula 2,
R', R _x , R _y , R ₁ to R ₈ , R _a1 and R _a2 are the same or different at each occurrence and represent hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; , a substituted or unsubstituted cycloalkyl group having 3 to 20 ring atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 ring atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring 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 unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted Alkenyl group having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted 3 carbon atoms ~30 heteroaryl group, substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted 3 to 20 carbon atoms alkyl germanium group, substituted or unsubstituted aryl germanium 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, hydroxy group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof,
Adjacent substituents R', R _x , R _y , R _a1 , and R _a2 may be combined to form a ring,
Adjacent substituents R ₁ to R ₈ may be bonded to form a ring. )

According to one embodiment of the invention, X ₁ to X ₅ are selected from CR _x , the same or different at each occurrence.

According to one embodiment of the invention, Y ₁ to Y ₄ are selected from CR _y , the same or different at each occurrence.

According to one embodiment of the invention, at least one of X ₁ -X ₅ is N, for example one or two of X ₁ -X ₅ are N.

According to one embodiment of the invention, at least one of Y ₁ -Y ₄ is N, for example one or two of Y ₁ -Y ₄ are N.

According to one embodiment of the invention, X is selected from O or S.

According to one embodiment of the invention, X is selected from O.

According to one embodiment of the invention, a is selected from 0, 1, 2 or 3.

According to one embodiment of the invention, a is selected from 1.

According to an embodiment of the invention, R _a1 and R _a2 are the same or different at each occurrence, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted a cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted carbon atom 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, cyano group, isocyano group, hydroxyl group, selected from the group consisting of sulfanyl groups, and combinations thereof.

According to an embodiment of the invention, R _a1 and R _a2 are the same or different at each occurrence and are hydrogen, deuterium, substituted or unsubstituted C1-6 alkyl group, substituted or unsubstituted ring Cycloalkyl group having 3 to 6 carbon atoms, substituted or unsubstituted aryl group having 6 to 18 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 18 carbon atoms, substituted or unsubstituted number of carbon atoms selected from the group consisting of 3 to 15 alkylsilyl groups, and combinations thereof.

According to an embodiment of the invention, R _a1 and R _a2 are the same or different at each occurrence and are hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert -Butyl group, cyclopentyl group, cyclohexyl group, deuterated methyl group, deuterated ethyl group, deuterated propyl group, deuterated isopropyl group, deuterated n-butyl group, deuterated isobutyl group, deuterium tert-butyl group, deuterated cyclopentyl group, deuterated cyclohexyl group, phenyl group, pyridyl group, trimethylsilyl group, and combinations thereof.

According to an embodiment of the present invention, in Ar, ring Ar ₁ and ring Ar ₂ are the same or different at each occurrence, and are aromatic rings having 6 to 18 ring atoms, heteroaromatic rings having 5 to 18 ring atoms. is selected from rings or a combination thereof, and the total number of ring atoms of ring Ar ₁ and ring Ar ₂ is 8 or more and 30 or less.

According to one embodiment of the present invention, the total number of ring atoms of ring Ar ₁ and ring Ar ₂ in Ar is 8 or more and 24 or less.

According to one embodiment of the present invention, the total number of ring atoms of ring Ar ₁ and ring Ar ₂ in Ar is 8 or more and 18 or less.

According to an embodiment of the invention, in Ar, ring Ar ₁ and ring Ar ₂ are the same or different at each occurrence and are an aromatic ring having 6 ring atoms or a heteroaromatic ring having 5 or 6 ring atoms. , or a combination thereof.

According to one embodiment of the invention, in Ar, ring Ar ₁ and ring Ar ₂ are the same or different at each occurrence and are selected from aromatic or heteroaromatic rings having 6 ring atoms.

According to one embodiment of the invention, in Ar, ring Ar ₁ and ring Ar ₂ are the same or different at each occurrence and are selected from aromatic rings having 6 ring atoms.

According to an embodiment of the present invention, in Ar, ring Ar ₁ and ring Ar ₂ are the same or different at each occurrence, such as a benzene ring, a pyridine ring, a pyrimidine ring, a naphthalene ring, a triazine ring, a phenanthrene ring, an anthracene ring, Silicon fluorene ring, quinoline ring, isoquinoline ring, benzofuran ring, fused bithiophene ring, fused bifuran ring, benzothiophene ring, indene ring, dibenzofuran ring, dibenzothiophene ring, triphenylene ring, carbazole ring, azacarbazole ring, azadibenzofuran ring, aza It is selected from the group consisting of a dibenzothiophene ring, an azasilicon fluorene ring, and a combination thereof, and the total number of ring atoms of ring Ar ₁ and ring Ar ₂ is 8 or more and 30 or less.

からなる群から選ばれ、
上記基は、一部または全部重水素化されていてもよく、

は、前記Ａｒの結合箇所を表す。 According to one embodiment of the invention, Ar may be the same or different at each occurrence.

selected from the group consisting of
The above group may be partially or fully deuterated,

represents the bonding location of Ar.

According to one embodiment of the invention, R _x is hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted ring carbon Cycloalkyl group having 3 to 20 atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted 3 carbon atoms -20 alkylsilyl groups, cyano groups, and combinations thereof.

According to one embodiment of the invention, R _x is hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, substituted or unsubstituted ring carbon Cycloalkyl group having 3 to 6 atoms, substituted or unsubstituted aryl group having 6 to 12 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, substituted or unsubstituted 3 carbon atoms -6 alkylsilyl groups, cyano groups, and combinations thereof.

According to an embodiment of the present invention, at least one of the _R Cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted 3 to 20 carbon atoms selected from the group consisting of alkylsilyl groups, cyano groups, and combinations thereof.

According to one embodiment of the invention, at least one of _R -6 cycloalkyl group, substituted or unsubstituted aryl group having 6 to 12 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, substituted or unsubstituted 3 to 6 carbon atoms selected from the group consisting of alkylsilyl groups, cyano groups, and combinations thereof.

According to one embodiment of the invention, at least one of _R -6 cycloalkyl groups, cyano groups, and combinations thereof.

According to one embodiment of the invention, at least one of X ₁ to X ₅ is selected from CR _x , and said R _x is a cyano group or fluorine.

According to one embodiment of the invention, at least one of X ₃ to X ₅ is selected from CR _x , and said R _x is a cyano group or fluorine.

According to one embodiment of the invention, X ₅ is CR _x and R _x is cyano or fluorine.

According to an embodiment of the invention, R _y is the same or different at each occurrence, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted ring carbon Cycloalkyl group having 3 to 20 atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted 3 carbon atoms -20 alkylsilyl groups, and combinations thereof.

According to an embodiment of the invention, R _y is the same or different at each occurrence, hydrogen, deuterium, substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, substituted or unsubstituted number of ring carbon atoms; Cycloalkyl group having 3 to 6 carbon atoms, substituted or unsubstituted aryl group having 6 to 18 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 18 carbon atoms, substituted or unsubstituted 3 to 15 carbon atoms alkylsilyl groups, and combinations thereof.

According to one embodiment of the invention, at least one R _y is deuterium, halogen, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted C3-C20 alkyl group, substituted or unsubstituted C3-C20 alkyl group, It is selected from the group consisting of a cycloalkyl group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and a combination thereof.

According to an embodiment of the invention, at least one or at least two or at least three or all of R ₂ , R ₃ , R ₆ , R ₇ is deuterium, substituted or unsubstituted number of carbon atoms. 1-20 alkyl group, substituted or unsubstituted cycloalkyl group having 3-20 ring carbon atoms, substituted or unsubstituted aryl group having 6-30 carbon atoms, substituted or unsubstituted 3-30 carbon atoms heteroaryl groups, and combinations thereof.

According to an embodiment of the invention, at least one or at least two or at least three or all of R ₂ , R ₃ , R ₆ , R ₇ is deuterium, substituted or unsubstituted number of carbon atoms. selected from the group consisting of alkyl groups of 1 to 20, substituted or unsubstituted cycloalkyl groups of 3 to 20 ring carbon atoms, and combinations thereof.

According to an embodiment of the invention, at least one or at least two or at least three or all of R ₂ , R ₃ , R ₆ , R ₇ are deuterium, methyl, ethyl, propyl. , isopropyl group, n-butyl group, isobutyl group, tert-butyl group, cyclopentyl group, cyclohexyl group, neopentyl group, tert-pentyl group, and combinations thereof, and some of the hydrogens in the above group are Alternatively, it may be entirely deuterated.

According to one embodiment of the invention, R' is selected from substituted or unsubstituted alkyl groups having 1 to 20 ring carbon atoms, or substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms.

According to one embodiment of the invention, R' is a methyl group or a deuterated methyl group.

According to one embodiment of the invention, R ₇ is the same or different at each occurrence, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted ring carbon Cycloalkyl group having 3 to 20 atoms, substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted carbon atom number aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted aryloxy group having 2 to 20 carbon atoms Alkenyl group, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted amino group having 0 to 20 carbon atoms, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxy group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof.

およびからなる群から選ばれるいずれか１種である。 According to one embodiment of the invention, L _a is selected from the group consisting of L _a1 to L _a1177 , the same or different for each occurrence .

Any one selected from the group consisting of and.

According to one embodiment of the invention, L _b is selected from the group consisting of L _b1 to L _b128 , the same or different for each occurrence .

According to one embodiment of the invention, L _c is selected from the group consisting of L _c1 to L _c360 , the same or different for each occurrence .

According to one embodiment of the invention, the metal complex has the structure Ir(L _a ) ₂ (L _b ), where L _a is the same or different at each occurrence from the group consisting of L _a1 to L _a1177 . L _b is any one selected from the group consisting of L _b1 to L _b128 . Specific structures of L _a1 to L _a1177 are shown in claim 16, and specific structures of L _b1 to L _b128 are shown in claim 17.

According to one embodiment of the invention, the metal complex has the structure Ir(L _a )(L _b ) ₂ , where L _a is the same or different at each occurrence from the group consisting of L _a1 to L _a1177 . L _b is one selected from the group consisting of L _b1 to L b128, or two selected from the group consisting of L b1 to L _b128 . Specific structures of L _a1 to L _a1177 are shown in claim 16, and specific structures of L _b1 to L _b128 are shown in claim 17.

According to one embodiment of the present invention, the metal complex has a structure of Ir(L _a ) ₃ , where L _a is the same or different at each occurrence and is any one selected from the group consisting of L _a1 to L _a1177 . One type, any two types, or any three types. The specific structures of L _a1 to L _a1177 are shown in claim 16.

According to one embodiment of the invention, the metal complex has the structure Ir(L _a ) ₂ (L _c ), where L _a is the same or different at each occurrence from the group consisting of L _a1 to L _a1177 . One or two selected types, and L _c is any one selected from the group consisting of L _c1 to L _c360 . Specific structures of L _a1 to L _a1177 are shown in claim 16, and specific structures of L _c1 to L _c360 are shown in claim 18.

According to an embodiment of the invention, the metal complex has the structure Ir(L _a )(L _c ) ₂ , where L _a is the same or different at each occurrence from the group consisting of L _a1 to L _a1177 . L _c is any one selected from the group consisting of L _c1 to L _{c360, or two selected from the group consisting of L c1 to L c360} . Specific structures of L _a1 to L _a1177 are shown in claim 16, and specific structures of L _c1 to L _c360 are shown in claim 18.

According to one embodiment of the present invention, the metal complex has the structure Ir(L _a )(L _b )(L _c ), where L _a is the same or different at each occurrence from L _a1 to L _a1177 . L _b is any one selected from the group consisting of L _b1 to L _b128 , and L _c is any one selected from the group consisting of L _c1 to L _c360 . There is one type. The specific structures of L _a1 to L _a1177 are shown in claim 16, the specific structures of L _b1 to L _b128 are shown in claim 17, and the specific structures of L _c1 to L _c360 are: As shown in claim 18.

According to one embodiment of the invention, the metal complex is selected from the group consisting of Metal Complex 1 to Metal Complex 1008 .

According to one embodiment of the present invention, an electroluminescent device comprises an anode, a cathode, and an organic layer provided between the anode and the cathode, the organic layer being an electroluminescent device according to any one of the embodiments described above. Electroluminescent devices comprising the described metal complexes are disclosed.

According to an embodiment of the present invention, in the electroluminescent device, the organic layer containing the metal complex is a light emitting layer.

According to one embodiment of the invention, the light emitting layer in the electroluminescent device emits green light.

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

According to one embodiment of the present invention, the light emitting layer in the electroluminescent device includes a first host compound.

According to one embodiment of the present invention, the light emitting layer in the electroluminescent device includes a first host compound and a second host compound.

According to one embodiment of the present invention, in the electroluminescent device, at least one of the host compounds is benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazolyl, dibenzothiophene, aza At least one member selected from the group consisting of dibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorenyl, silicone fluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof. Contains chemical groups of.

（Ｅ_１～Ｅ_６は、出現毎に同一または異なってＣ、ＣＲ_ｅまたはＮから選ばれ、且つＥ_１～Ｅ_６のうちの少なくとも２つは、Ｎであり、Ｅ_１～Ｅ_６のうちの少なくとも１つは、Ｃであり、式Ａに結合し、

Ｑは、出現毎に同一または異なってＯ、Ｓ、Ｓｅ、Ｎ、ＮＲ’’、ＣＲ’’Ｒ’’、ＳｉＲ’’Ｒ’’、ＧｅＲ’’Ｒ’’およびＲ’’Ｃ＝ＣＲ’’からなる群から選ばれ、２つのＲ’’が同時に存在する場合、２つのＲ’’は、同一または異なってもよく、
ｐは、０または１であり、ｒは、０または１であり、
ＱがＮから選ばれる場合、ｐは、０であり、ｒは、１であり、
ＱがＯ、Ｓ、Ｓｅ、ＮＲ’’、ＣＲ’’Ｒ’’、ＳｉＲ’’Ｒ’’、ＧｅＲ’’Ｒ’’およびＲ’’Ｃ＝ＣＲ’’からなる群から選ばれる場合、ｐは、１であり、ｒは、０であり、
Ｌは、出現毎に同一または異なって単結合、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選ばれ、
Ｑ_１～Ｑ_８は、出現毎に同一または異なってＣ、ＣＲ_ｑまたはＮから選ばれ、
Ｒ_ｅ、Ｒ’’およびＲ_ｑ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環原子数３～２０のヘテロ環基、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２～２０のアルキニル基、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３～２０のアルキルゲルマニウム基、置換または非置換の炭素原子数６～２０のアリールゲルマニウム基、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、
「＊」は、式Ａと式４との結合箇所を表し、
隣り合う置換基Ｒ_ｅ、Ｒ’’、Ｒ_ｑは、結合して環を形成していてもよい。） According to one embodiment of the invention, the first host compound has a structure represented by Formula 4.

(E ₁ to E ₆ are the same or different for each occurrence and are selected from C, CR _e, or N, and at least two of E ₁ to E ₆ are N; and at least two of E ₁ to E ₆ are N; at least one of is C and is bonded to formula A;

Q may be the same or different for each occurrence and may be O, S, Se, N, NR'', CR''R'', SiR''R'', GeR''R'' and R''C=CR'', and when two R'' are present at the same time, the two R'' may be the same or different;
p is 0 or 1, r is 0 or 1,
If Q is chosen from N, p is 0, r is 1,
If Q is selected from the group consisting of O, S, Se, NR'', CR''R'', SiR''R'', GeR''R'' and R''C=CR'', then p is 1, r is 0,
L is the same or different for each occurrence; a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted carbon selected from an arylene group having 6 to 20 atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;
Q ₁ to Q ₈ are the same or different for each occurrence and are selected from C, CR _q or N,
R _e , R'' and R _q are the same or different at each occurrence, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted ring carbon number 3 ~20 cycloalkyl group, substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted heterocyclic group having 7 to 30 carbon atoms an aralkyl group, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, Substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, 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, substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, substituted or unsubstituted carbon Arylgermanium group having 6 to 20 atoms, substituted or unsubstituted amine group having 0 to 20 carbon atoms, acyl group, carbonyl group, carboxyl group, ester group, cyano group, isocyano group, hydroxy group, sulfanyl group, sulfinyl selected from the group consisting of a sulfonyl group, a sulfonyl group, a phosphino group, and combinations thereof;
"*" represents the connection point between formula A and formula 4,
Adjacent substituents R _e , R'', and R _q may be bonded to form a ring. )

In this specification, "adjacent substituents R _e , R'', R _q may be bonded to form a ring" means adjacent substituent groups, for example, two substituents R _e , two substituents R'', two substituents _Rq , and substituents R'' and _Rq may be bonded together to form a ring. means. Obviously, none of these substituents need be linked together to form a ring.

According to an embodiment of the invention, E ₁ to E ₆ are selected from C, CR _e or N, the same or different at each occurrence, and three of E ₁ to E ₆ are N. , E ₁ to E ₆ is CR _e , and R _e is the same or different at each occurrence and is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted. selected from the group consisting of substituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof.

According to an embodiment of the invention, E ₁ to E ₆ are selected from C, CR _e or N, the same or different at each occurrence, and three of E ₁ to E ₆ are N. , E ₁ to E ₆ is CR _e , and R _e is the same or different at each occurrence and is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or Unsubstituted terphenyl group, substituted or unsubstituted naphthalene group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted triphenylene group, substituted or unsubstituted fluorene group, substituted or unsubstituted dibenzofuran group, substituted or unsubstituted selected from the group consisting of substituted dibenzothiophene groups, substituted or unsubstituted carbazolyl groups, and combinations thereof.

According to one embodiment of the invention, Q is selected from O, S, N or NR'', the same or different on each occurrence.

According to an embodiment of the invention, at least one or at least two of Q ₁ to Q ₈ are selected from CR _q , and R _q is substituted or unsubstituted and has 6 to 30 carbon atoms. aryl group, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms, or a combination thereof.

According to an embodiment of the invention, at least one or at least two of Q ₁ to Q ₈ are selected from CR _q , and R _q is a substituted or unsubstituted phenyl group, a substituted or unsubstituted phenyl group, selected from a substituted naphthalene group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted pyridyl group, or a combination thereof.

According to one embodiment of the invention, L is the same or different at each occurrence, and is a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted arylene group having 3 to 20 carbon atoms, selected from heteroarylene groups, or combinations thereof.

According to an embodiment of the invention, L is the same or different at each occurrence, and is a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted carbazolilidene group, a substituted or unsubstituted carbazolilidene group, It is selected from a substituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group, and a substituted or unsubstituted fluorenyl group.

According to one embodiment of the invention, L is the same or different at each occurrence and is selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group.

からなる群から選ばれる。 According to one embodiment of the invention, the first host compound is selected from the group consisting of H-1 to H-243 .

selected from the group consisting of.

（Ｌ_ｘは、出現毎に同一または異なって単結合、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選ばれ、
Ｖは、出現毎に同一または異なってＣ、ＣＲ_ｖまたはＮから選ばれ、且つＶのうちの少なくとも１つは、Ｃであり、Ｌ_ｘに結合し、
Ｕは、出現毎に同一または異なってＣ、ＣＲ_ｕまたはＮから選ばれ、且つＵのうちの少なくとも１つは、Ｃであり、Ｌ_ｘに結合し、
Ｒ_ｖおよびＲ_ｕ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環原子数３～２０のヘテロ環基、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２～２０のアルキニル基、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３～２０のアルキルゲルマニウム基、置換または非置換の炭素原子数６～２０のアリールゲルマニウム基、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、
Ａｒ_６は、出現毎に同一または異なって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、またはこれらの組合せから選ばれ、
隣り合う置換基Ｒ_ｖおよびＲ_ｕは、結合して環を形成していてもよい。） According to one embodiment of the present invention, in the electroluminescent device, the second host compound has a structure represented by Formula 5.

( _L selected from an arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof,
V is selected from C, CR _v or N, the same or different at each occurrence, and at least one of V is C and is bonded to L _x ;
U is selected from C, CR _u or N, the same or different at each occurrence, and at least one of U is C and is bonded to L _x ;
R _v and R _u are the same or different at each occurrence, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 ring carbon atoms, substituted or unsubstituted cyclocarbon having 3 to 20 ring atoms; Alkyl group, substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl group having 7 to 30 ring atoms, Substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; Alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, substituted or unsubstituted 6 to 20 carbon atoms 20 aryl germanium groups, substituted or unsubstituted amine groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxy groups, sulfanyl groups, sulfinyl groups, sulfonyl groups , a phosphino group, and combinations thereof;
Ar ₆ is the same or different at each occurrence and is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof;
Adjacent substituents R _v and R _u may be bonded to form a ring. )

In the examples, "adjacent substituents R _v and R _u may combine to form a ring" means adjacent substituent groups, for example, two substituents R _v each other, two substituents It means that any one or more of the groups R _u , the substituents R _v and the R _u groups may be bonded to each other to form a ring. Obviously, none of these substituents need be linked together to form a ring.

（Ｌ_ｘは、出現毎に同一または異なって単結合、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選ばれ、
Ｖは、出現毎に同一または異なってＣＲ_ｖまたはＮから選ばれ、
Ｕは、出現毎に同一または異なってＣＲ_ｕまたはＮから選ばれ、
Ｒ_ｖおよびＲ_ｕ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環原子数３～２０のヘテロ環基、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２～２０のアルキニル基、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３～２０のアルキルゲルマニウム基、置換または非置換の炭素原子数６～２０のアリールゲルマニウム基、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、
Ａｒ_６は、出現毎に同一または異なって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、またはこれらの組合せから選ばれ、
隣り合う置換基Ｒ_ｖおよびＲ_ｕは、結合して環を形成していてもよい。） According to one embodiment of the present invention, in the electroluminescent device, the second host compound has a structure represented by one of formulas 5-a to 5-j.

( _L selected from an arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof,
V is selected from CR _v or N, the same or different at each occurrence;
U is selected from CR _u or N, the same or different for each occurrence;
R _v and R _u are the same or different at each occurrence, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 ring carbon atoms, substituted or unsubstituted cyclocarbon having 3 to 20 ring atoms; Alkyl group, substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl group having 7 to 30 ring atoms, Substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; Alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, substituted or unsubstituted 6 to 20 carbon atoms 20 aryl germanium groups, substituted or unsubstituted amine groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxyl groups, ester groups, cyano groups, isocyano groups, hydroxy groups, sulfanyl groups, sulfinyl groups, sulfonyl groups , a phosphino group, and combinations thereof;
Ar ₆ is the same or different at each occurrence and is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof;
Adjacent substituents R _v and R _u may be bonded to form a ring. )

According to one embodiment of the invention, the second host compound is selected from the group consisting of compounds X-1 to X-128 .

According to an embodiment of the present invention, in the electroluminescent device, when the first host compound and the second host compound are doped with a metal complex, the weight of the metal complex is 1% of the total weight of the light emitting layer. ~30%.

According to an embodiment of the present invention, in the electroluminescent device, when the first host compound and the second host compound are doped with a metal complex, the weight of the metal complex is 3% of the total weight of the light emitting layer. ~13%.

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

Combination with other materials

The materials of the particular layers used in the organic light emitting devices described in this invention can be used in combination with various other materials present in the device. Combinations of these materials are described in detail in US patent application US2016/0359122A1, paragraphs 0132-0161, the entire content of which is incorporated herein by reference. The materials described or referred to are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art will readily refer to the literature to determine which materials can be used in combination with the compounds disclosed herein. Other materials can be identified.

It is stated herein that the specific layer materials used in organic light emitting devices can be used in combination with a wide variety of other materials present in the device. Illustratively, the emissive 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. These material combinations are described in detail in patent application US2015/0349273A1, paragraphs 0080-0101, the contents of which are fully incorporated herein by reference. The materials described or referred to are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art will readily refer to the literature to determine which materials can be used in combination with the compounds disclosed herein. Other materials can be identified.

In the material synthesis examples, all reactions are performed with nitrogen protection unless otherwise stated. All reaction solvents are anhydrous and used as obtained from commercial sources. The product to be synthesized may be subjected to one or more instruments conventional in the art (Bruker nuclear magnetic resonance apparatus, Shimadzu liquid chromatography, liquid chromatography/mass spectrometer, gas chromatography/mass spectrometer). , a differential thermal scanning calorimetry device, a fluorescence spectrophotometer manufactured by Shanghai Liang Optical Technology, an electrochemical work station manufactured by Wuhan Kesi Special, and a sublimation device manufactured by Anhui Beike). , structure confirmation and property testing were performed using methods familiar to those skilled in the art. In the example of the device, the characteristics of the device were evaluated using equipment commonly used in this field (e.g., a vapor deposition machine manufactured by Angstrom Engineering, an optical test system manufactured by Suzhou Fushida, a service life test system, an ellipsometer manufactured by Beijing Q&A, etc.). (including, but not limited to), using methods familiar to those skilled in the art. Those skilled in the art are familiar with the above-mentioned use of equipment, testing methods, etc., so that the specific data of the sample can be obtained reliably and unaffected, so the above-mentioned relevant details are repeated herein. I won't explain.

Example of material synthesis

The method for preparing the compounds according to the invention is not limited. Taking the following typical but non-limiting examples as examples, their synthetic routes and preparation methods are as follows.

Synthesis Example 1: Synthesis of Metal Complex 127

５００ｍＬの乾燥した丸底フラスコに、５－メチル－２－フェニルピリジン（１０．０ｇ、５９．２ｍｍｏｌ）、三塩化イリジウム三水和物（５．０ｇ、１４．２ｍｍｏｌ）、２－エトキシエタノール３００ｍＬ、水１００ｍＬを順に添加した。窒素ガスで３回置換し、窒素ガスの保護下で、１３０℃で２４ｈ加熱しながら撹拌した。冷却した後、濾過し、メタノールおよびｎ－ヘキサンでそれぞれ３回リンスした。乾燥まで汲み上げて７．５ｇの黄色固定である中間体１（収率９７％）を得た。 Step 1:

In a 500 mL dry round bottom flask, 5-methyl-2-phenylpyridine (10.0 g, 59.2 mmol), iridium trichloride trihydrate (5.0 g, 14.2 mmol), 300 mL of 2-ethoxyethanol, 100 mL of water was added in turn. The atmosphere was replaced with nitrogen gas three times, and the mixture was stirred while heating at 130° C. for 24 hours under the protection of nitrogen gas. After cooling, it was filtered and rinsed three times each with methanol and n-hexane. Pumping to dryness yielded 7.5 g of intermediate 1 (97% yield), a yellow solid.

５００ｍＬの乾燥した丸底フラスコに、中間体１（７．５ｇ、６．８ｍｍｏｌ）、無水ジクロロメタン２５０ｍＬ、メタノール１０ｍＬ、シルバートリフラート（Ｓｉｌｖｅｒ ｔｒｉｆｌａｔｅ）（３．８ｇ、１４．８ｍｍｏｌ）を順に添加した。窒素ガスで３回置換し、窒素ガスの保護下で、室温で１晩撹拌した。珪藻土で濾過し、ジクロロメタンで２回リンスし、下方における有機相を回収し、減圧し、濃縮させて９．２ｇの中間体２（収率９３％）を得た。 Step 2:

Intermediate 1 (7.5 g, 6.8 mmol), 250 mL of anhydrous dichloromethane, 10 mL of methanol, and Silver triflate (3.8 g, 14.8 mmol) were sequentially added to a 500 mL dry round bottom flask. The atmosphere was purged with nitrogen gas three times, and the mixture was stirred overnight at room temperature under the protection of nitrogen gas. After filtering through diatomaceous earth and rinsing twice with dichloromethane, the lower organic phase was collected, vacuumed, and concentrated to yield 9.2 g of intermediate 2 (93% yield).

５００ｍＬの乾燥した丸底フラスコに、中間体２（１．３ｇ、１．７ｍｍｏｌ）、中間体３（０．９ｇ、２．３ｍｍｏｌ）、エタノール２５０ｍＬを順に添加した。窒素ガスで３回置換し、窒素ガスの保護下で、１００℃で１８ｈ加熱しながら反応させた。反応が冷却した後、珪藻土で濾過した。メタノール、ｎ－ヘキサンでそれぞれ２回洗浄した。珪藻土の上方における黄色固体をジクロロメタンで溶解させ、有機相を回収し、減圧し、濃縮させた。シリカゲルカラムクロマトグラフィーで精製して、黄色の固体生成物である金属錯体１２７（０．７５ｇ、収率４７．７％）を得た。生成物は、分子量が９２５．３の目標生成物として確認された。 Step 3:

Intermediate 2 (1.3 g, 1.7 mmol), Intermediate 3 (0.9 g, 2.3 mmol), and 250 mL of ethanol were sequentially added to a 500 mL dry round bottom flask. The atmosphere was replaced with nitrogen gas three times, and the reaction was carried out while heating at 100° C. for 18 hours under the protection of nitrogen gas. After the reaction was cooled, it was filtered through diatomaceous earth. It was washed twice with methanol and n-hexane, respectively. The yellow solid above the diatomaceous earth was dissolved with dichloromethane and the organic phase was collected, vacuumed and concentrated. Purification by silica gel column chromatography gave a yellow solid product, metal complex 127 (0.75 g, yield 47.7%). The product was confirmed as the target product with a molecular weight of 925.3.

Synthesis Example 2: Synthesis of Metal Complex 505

５００ｍＬの乾燥した丸底フラスコに、５－ｔｅｒｔ－ブチル－２－フェニルピリジン（１３．２ｇ、６２．９ｍｍｏｌ）、三塩化イリジウム三水和物（５．５ｇ、１５．７ｍｍｏｌ）、２－エトキシエタノール３００ｍＬ、水１００ｍＬを順に添加した。窒素ガスで３回置換し、窒素ガスの保護下で、１３０℃で２４ｈ加熱しながら撹拌した。冷却した後、濾過し、メタノールおよびｎ－ヘキサンでそれぞれ３回リンスした。乾燥まで汲み上げて９．７ｇの中間体４（収率９７％）を得た。 Step 1:

In a 500 mL dry round bottom flask, add 5-tert-butyl-2-phenylpyridine (13.2 g, 62.9 mmol), iridium trichloride trihydrate (5.5 g, 15.7 mmol), 2-ethoxyethanol. 300 mL and 100 mL of water were added in this order. The atmosphere was replaced with nitrogen gas three times, and the mixture was stirred while heating at 130° C. for 24 hours under the protection of nitrogen gas. After cooling, it was filtered and rinsed three times each with methanol and n-hexane. Pumping to dryness yielded 9.7 g of intermediate 4 (97% yield).

５００ｍＬの乾燥した丸底フラスコに、中間体４（９．７ｇ、７．７ｍｍｏｌ）、無水ジクロロメタン２５０ｍＬ、メタノール１０ｍＬ、シルバートリフラート（４．３ｇ、１６．７ｍｍｏｌ）を順に添加した。窒素ガスで３回置換し、窒素ガスの保護下で、室温で１晩撹拌した。珪藻土で濾過し、ジクロロメタンで２回リンスし、下方における有機相を回収し、減圧し、濃縮させて、１３．２ｇ黄色固定である中間体５（収率９３％）を得た。 Step 2:

Intermediate 4 (9.7 g, 7.7 mmol), 250 mL of anhydrous dichloromethane, 10 mL of methanol, and silver triflate (4.3 g, 16.7 mmol) were sequentially added to a 500 mL dry round bottom flask. The atmosphere was purged with nitrogen gas three times, and the mixture was stirred overnight at room temperature under the protection of nitrogen gas. After filtering through diatomaceous earth and rinsing twice with dichloromethane, the lower organic phase was collected, vacuumed, and concentrated to yield 13.2 g of intermediate 5 (93% yield) as a yellow solid.

５００ｍＬの乾燥した丸底フラスコに、中間体５（１．４ｇ、１．８ｍｍｏｌ）、中間体３（０．９ｇ、２．２ｍｍｏｌ）、エタノール３００ｍＬを順に添加した。窒素ガスで３回置換し、窒素ガスの保護下で、１００℃で２４ｈ加熱しながら反応させた。反応が冷却した後、珪藻土で濾過した。メタノール、ｎ－ヘキサンでそれぞれ２回洗浄した。珪藻土の上方における黄色固体をジクロロメタンで溶解させ、有機相を回収し、減圧し、濃縮させた。シリカゲルカラムクロマトグラフィーで精製して、黄色の固体生成物である金属錯体５０５（０．７５ｇ、収率４１．３％）を得た。生成物は、分子量が１００９．４の目標生成物として確認された。 Step 3:

Intermediate 5 (1.4 g, 1.8 mmol), Intermediate 3 (0.9 g, 2.2 mmol), and 300 mL of ethanol were sequentially added to a 500 mL dry round bottom flask. The atmosphere was replaced with nitrogen gas three times, and the reaction was carried out while heating at 100° C. for 24 hours under the protection of nitrogen gas. After the reaction was cooled, it was filtered through diatomaceous earth. It was washed twice with methanol and n-hexane, respectively. The yellow solid above the diatomaceous earth was dissolved with dichloromethane and the organic phase was collected, vacuumed and concentrated. Purification by silica gel column chromatography gave a yellow solid product, metal complex 505 (0.75 g, yield 41.3%). The product was confirmed as the target product with a molecular weight of 1009.4.

Synthesis Example 3: Synthesis of Metal Complex 520

２５０ｍＬの乾燥した丸底フラスコに、順に、中間体６（２．０ｇ、４．９ｍｍｏｌ）、中間体５（２．７ｇ、３．３ｍｍｏｌ）、２－エトキシエタノールおよびＮ，Ｎ－ジメチルホルムアミドをそれぞれ５０ｍＬ添加した。窒素ガスで３回置換し、窒素ガスの保護下で、１００℃で９６ｈ加熱しながら反応させた。反応が冷却した後、珪藻土で濾過した。メタノール、ｎ－ヘキサンでそれぞれ２回洗浄した。珪藻土の上方における黄色固体をジクロロメタンで溶解させ、有機相を回収し、減圧し、濃縮させた。シリカゲルカラムクロマトグラフィーで精製して、黄色の固体生成物である金属錯体５２０（１．７４ｇ、収率５１．５％）を得た。生成物は、分子量が１０２３．４の目標生成物として確認された。 Step 1:

In a 250 mL dry round bottom flask, intermediate 6 (2.0 g, 4.9 mmol), intermediate 5 (2.7 g, 3.3 mmol), 2-ethoxyethanol and N,N-dimethylformamide were added in order. 50 mL was added. The atmosphere was replaced with nitrogen gas three times, and the reaction was carried out while heating at 100° C. for 96 hours under the protection of nitrogen gas. After the reaction was cooled, it was filtered through diatomaceous earth. It was washed twice with methanol and n-hexane, respectively. The yellow solid above the diatomaceous earth was dissolved with dichloromethane and the organic phase was collected, vacuumed and concentrated. Purification by silica gel column chromatography gave a yellow solid product, metal complex 520 (1.74 g, yield 51.5%). The product was confirmed as the target product with a molecular weight of 1023.4.

Synthesis Example 4: Synthesis of Metal Complex 532

５００ｍＬの乾燥した丸底フラスコに、中間体７（１．８ｇ、４．５ｍｍｏｌ）、中間体５（２．５ｇ、３．０ｍｍｏｌ）、エタノール３００ｍＬを順に添加した。窒素ガスで３回置換し、窒素ガスの保護下で、１００℃で２４ｈ加熱しながら反応させた。反応が冷却した後、珪藻土で濾過した。メタノール、ｎ－ヘキサンでそれぞれ２回洗浄した。珪藻土の上方における黄色固体をジクロロメタンで溶解させ、有機相を回収し、減圧し、濃縮させた。シリカゲルカラムクロマトグラフィーで精製して、黄色の固体生成物である金属錯体５３２（０．５５ｇ、収率１８．２％）を得た。生成物は、分子量が１００９．４の目標生成物として確認された。 Step 1:

Intermediate 7 (1.8 g, 4.5 mmol), Intermediate 5 (2.5 g, 3.0 mmol), and 300 mL of ethanol were sequentially added to a 500 mL dry round bottom flask. The atmosphere was replaced with nitrogen gas three times, and the reaction was carried out while heating at 100° C. for 24 hours under the protection of nitrogen gas. After the reaction was cooled, it was filtered through diatomaceous earth. It was washed twice with methanol and n-hexane, respectively. The yellow solid above the diatomaceous earth was dissolved with dichloromethane and the organic phase was collected, vacuumed and concentrated. Purification by silica gel column chromatography gave a yellow solid product, metal complex 532 (0.55 g, yield 18.2%). The product was confirmed as the target product with a molecular weight of 1009.4.

Synthesis Example 5: Synthesis of Metal Complex 181

５００ｍＬの乾燥した丸底フラスコに、中間体２（２．６ｇ、３．５ｍｍｏｌ）、中間体８（２．２ｇ、５．３ｍｍｏｌ）、エタノール２５０ｍＬを順に添加した。窒素ガスで３回置換し、窒素ガスの保護下で、１００℃で１８ｈ加熱しながら反応させた。反応が冷却した後、珪藻土で濾過した。メタノール、ｎ－ヘキサンでそれぞれ２回洗浄した。珪藻土の上方における黄色固体をジクロロメタンで溶解させ、有機相を回収し、減圧し、濃縮させた。シリカゲルカラムクロマトグラフィーで精製して、黄色の固体生成物である金属錯体１８１（１．１ｇ、収率３３．３％）を得た。生成物は、分子量が９４３．２の目標生成物として確認された。 Step 1:

Intermediate 2 (2.6 g, 3.5 mmol), Intermediate 8 (2.2 g, 5.3 mmol), and 250 mL of ethanol were sequentially added to a 500 mL dry round bottom flask. The atmosphere was replaced with nitrogen gas three times, and the reaction was carried out while heating at 100° C. for 18 hours under the protection of nitrogen gas. After the reaction was cooled, it was filtered through diatomaceous earth. It was washed twice with methanol and n-hexane, respectively. The yellow solid above the diatomaceous earth was dissolved with dichloromethane and the organic phase was collected, vacuumed and concentrated. Purification by silica gel column chromatography gave a yellow solid product, metal complex 181 (1.1 g, yield 33.3%). The product was confirmed as the target product with a molecular weight of 943.2.

Synthesis Example 6: Synthesis of Metal Complex 559

５００ｍＬの乾燥した丸底フラスコに、中間体５（２．１ｇ、２．６ｍｍｏｌ）、中間体８（１．５ｇ、３．６ｍｍｏｌ）、エタノール３００ｍＬを順に添加した。窒素ガスで３回置換し、窒素ガスの保護下で、１００℃で２４ｈ加熱しながら反応させた。反応が冷却した後、珪藻土で濾過した。メタノール、ｎ－ヘキサンでそれぞれ２回洗浄した。珪藻土の上方における黄色固体をジクロロメタンで溶解させ、有機相を回収し、減圧し、濃縮させた。シリカゲルカラムクロマトグラフィーで精製して、黄色の固体生成物である金属錯体５５９（１．３０ｇ、収率４８．７％）を得た。生成物は、分子量が１０２７．３の目標生成物として確認された。 Step 1:

Intermediate 5 (2.1 g, 2.6 mmol), Intermediate 8 (1.5 g, 3.6 mmol), and 300 mL of ethanol were sequentially added to a 500 mL dry round bottom flask. The atmosphere was replaced with nitrogen gas three times, and the reaction was carried out while heating at 100° C. for 24 hours under the protection of nitrogen gas. After the reaction was cooled, it was filtered through diatomaceous earth. It was washed twice with methanol and n-hexane, respectively. The yellow solid above the diatomaceous earth was dissolved with dichloromethane and the organic phase was collected, vacuumed and concentrated. Purification by silica gel column chromatography gave a yellow solid product, metal complex 559 (1.30 g, yield 48.7%). The product was confirmed as the target product with a molecular weight of 1027.3.

Synthesis Example 7: Synthesis of Metal Complex 197

２５０ｍＬの乾燥した丸底フラスコに、順に、中間体２（２．０ｇ、２．８ｍｍｏｌ）、中間体９（１．８ｇ、３．９ｍｍｏｌ）、２－エトキシエタノールおよびＮ，Ｎ－ジメチルホルムアミドをそれぞれ５０ｍＬ添加した。窒素ガスで３回置換し、窒素ガスの保護下で、１００℃で７２ｈ加熱しながら反応させた。反応が冷却した後、珪藻土で濾過した。メタノール、ｎ－ヘキサンでそれぞれ２回洗浄した。珪藻土の上方における黄色固体をジクロロメタンで溶解させ、有機相を回収し、減圧し、濃縮させた。シリカゲルカラムクロマトグラフィーで精製して、黄色の固体生成物である金属錯体１９７（１．２ｇ、収率４３．４％）を得、黄色固体である。生成物は、分子量が１００６．３の目標生成物として確認された。 Step 1:

In a 250 mL dry round bottom flask, intermediate 2 (2.0 g, 2.8 mmol), intermediate 9 (1.8 g, 3.9 mmol), 2-ethoxyethanol and N,N-dimethylformamide were added in order. 50 mL was added. The atmosphere was replaced with nitrogen gas three times, and the reaction was carried out while heating at 100° C. for 72 hours under the protection of nitrogen gas. After the reaction was cooled, it was filtered through diatomaceous earth. It was washed twice with methanol and n-hexane, respectively. The yellow solid above the diatomaceous earth was dissolved with dichloromethane and the organic phase was collected, vacuumed and concentrated. Purification by silica gel column chromatography gave metal complex 197 (1.2 g, yield 43.4%), a yellow solid product. The product was confirmed as the target product with a molecular weight of 1006.3.

Synthesis Example 8: Synthesis of Metal Complex 460

２５０ｍＬの乾燥した丸底フラスコに、４－（メチル－ｄ_３）－２－フェニルピリジン－５－ｄ（５．０ｇ、２８．９ｍｍｏｌ）、三塩化イリジウム三水和物（２．６ｇ、７．４ｍｍｏｌ）、２－エトキシエタノール（６０ｍＬ）および水（２０ｍＬ）を順に添加した。窒素ガスの保護下で、還流するまでに加熱し、２４ｈ撹拌した。冷却した後、減圧し、吸引濾過し、メタノールおよびｎ－ヘキサンでそれぞれ３回洗浄して、４．０ｇの黄色固定である中間体１０（収率９４．８％）を得た。 Step 1:

In a 250 mL dry round bottom flask were added 4-(methyl-d ₃ )-2-phenylpyridine-5-d (5.0 g, 28.9 mmol), iridium trichloride trihydrate (2.6 g, 7. 4 mmol), 2-ethoxyethanol (60 mL) and water (20 mL) were sequentially added. Under the protection of nitrogen gas, it was heated to reflux and stirred for 24 h. After cooling, the mixture was vacuumed, filtered with suction, and washed three times each with methanol and n-hexane to obtain 4.0 g of intermediate 10 (94.8% yield) as a yellow fixation.

５００ｍＬの乾燥した丸底フラスコに、中間体１０（４．０ｇ、３．５ｍｍｏｌ）、無水ジクロロメタン（２５０ｍＬ）、メタノール（１０ｍＬ）、シルバートリフラート（１．９ｇ、７．６ｍｍｏｌ）を順に添加した。窒素ガスで３回置換し、窒素ガスの保護下で、室温で１晩撹拌した。珪藻土で濾過し、ジクロロメタンで２回洗浄し、下方における有機相を回収し、減圧し、濃縮させて５．１ｇの中間体１１（収率９７．４％）を得た。 Step 2:

Intermediate 10 (4.0 g, 3.5 mmol), anhydrous dichloromethane (250 mL), methanol (10 mL), and silver triflate (1.9 g, 7.6 mmol) were sequentially added to a 500 mL dry round bottom flask. The atmosphere was purged with nitrogen gas three times, and the mixture was stirred at room temperature overnight under the protection of nitrogen gas. After filtering through diatomaceous earth and washing twice with dichloromethane, the lower organic phase was collected, vacuumed, and concentrated to yield 5.1 g of intermediate 11 (97.4% yield).

２５０ｍＬの乾燥した丸底フラスコに、中間体１２（１．５ｇ、３．７ｍｍｏｌ）、中間体１１（２．１ｇ、２．２ｍｍｏｌ）、Ｎ，Ｎ－ジメチルホルムアミド５０ｍＬ、２－エトキシエタノール５０ｍＬを順に添加した。Ｎ_２の保護下で、還流するまでに加熱し、９６ｈ反応させた。反応が冷却した後、珪藻土で濾過した。メタノール、ｎ－ヘキサンでそれぞれ２回洗浄した。珪藻土の上方における黄色固体をジクロロメタンで溶解させ、有機相を回収し、減圧し、濃縮させた。シリカゲルカラムクロマトグラフィーで精製して、黄色の固体生成物である金属錯体４６０（０．８２ｇ、収率４０．０％）を得た。該生成物は、分子量が９３２．３の目標生成物として確認された。 Step 3:

In a 250 mL dry round bottom flask, intermediate 12 (1.5 g, 3.7 mmol), intermediate 11 (2.1 g, 2.2 mmol), 50 mL of N,N-dimethylformamide, and 50 mL of 2-ethoxyethanol were added in this order. Added. Under protection of _N2 , heat to reflux and react for 96 h. After the reaction was cooled, it was filtered through diatomaceous earth. It was washed twice with methanol and n-hexane, respectively. The yellow solid above the diatomaceous earth was dissolved with dichloromethane and the organic phase was collected, vacuumed and concentrated. Purification by silica gel column chromatography gave a yellow solid product, metal complex 460 (0.82 g, yield 40.0%). The product was confirmed as the target product with a molecular weight of 932.3.

Synthesis Example 9: Synthesis of Metal Complex 571

２５０ｍＬの乾燥した丸底フラスコに、順に、中間体１３（１．４ｇ、１．７ｍｍｏｌ）、中間体５（１．０ｇ、２．４ｍｍｏｌ）、２－エトキシエタノールおよびＮ，Ｎ－ジメチルホルムアミドをそれぞれ５０ｍＬ添加した。窒素ガスで３回置換し、窒素ガスの保護下で、１００℃で７２ｈ加熱しながら反応させた。反応が冷却した後、珪藻土で濾過した。メタノール、ｎ－ヘキサンでそれぞれ２回洗浄した。珪藻土の上方における黄色固体をジクロロメタンで溶解させ、有機相を回収し、減圧し、濃縮させた。シリカゲルカラムクロマトグラフィーで精製して、黄色の固体生成物である金属錯体５７１（０．５ｇ、収率２８．４％）を得た。生成物は、分子量が１０３４．３の目標生成物として確認された。 Step 1:

In a 250 mL dry round bottom flask, intermediate 13 (1.4 g, 1.7 mmol), intermediate 5 (1.0 g, 2.4 mmol), 2-ethoxyethanol, and N,N-dimethylformamide were added in order. 50 mL was added. The atmosphere was replaced with nitrogen gas three times, and the reaction was carried out while heating at 100° C. for 72 hours under the protection of nitrogen gas. After the reaction was cooled, it was filtered through diatomaceous earth. It was washed twice with methanol and n-hexane, respectively. The yellow solid above the diatomaceous earth was dissolved with dichloromethane and the organic phase was collected, vacuumed and concentrated. Purification by silica gel column chromatography gave a yellow solid product, metal complex 571 (0.5 g, yield 28.4%). The product was confirmed as the target product with a molecular weight of 1034.3.

Synthesis Example 10: Synthesis of Metal Complex 572

２５０ｍＬの乾燥した丸底フラスコに、順に、中間体５（２．４ｇ、２．９ｍｍｏｌ）、中間体１４（１．５ｇ、３．４ｍｍｏｌ）、２－エトキシエタノールおよびＮ，Ｎ－ジメチルホルムアミドをそれぞれ５０ｍＬ添加した。窒素ガスで３回置換し、窒素ガスの保護下で、１００℃で７２ｈ加熱しながら反応させた。反応が冷却した後、珪藻土で濾過した。メタノール、ｎ－ヘキサンでそれぞれ２回洗浄した。珪藻土の上方における黄色固体をジクロロメタンで溶解させ、有機相を回収し、減圧し、濃縮させた。シリカゲルカラムクロマトグラフィーで精製して、黄色の固体生成物である金属錯体５７２（０．７ｇ、収率２３．０％）を得た。生成物は、分子量が１０４８．４の目標生成物として確認された。 Step 1:

In a 250 mL dry round bottom flask, intermediate 5 (2.4 g, 2.9 mmol), intermediate 14 (1.5 g, 3.4 mmol), 2-ethoxyethanol, and N,N-dimethylformamide were added in order. 50 mL was added. The atmosphere was replaced with nitrogen gas three times, and the reaction was carried out while heating at 100° C. for 72 hours under the protection of nitrogen gas. After the reaction was cooled, it was filtered through diatomaceous earth. It was washed twice with methanol and n-hexane, respectively. The yellow solid above the diatomaceous earth was dissolved with dichloromethane and the organic phase was collected, vacuumed and concentrated. Purification by silica gel column chromatography gave a yellow solid product, metal complex 572 (0.7 g, yield 23.0%). The product was confirmed as the target product with a molecular weight of 1048.4.

Synthesis Example 11: Synthesis of Metal Complex 579

２５０ｍＬの乾燥した丸底フラスコに、順に、中間体５（２．２ｇ、２．７ｍｍｏｌ）、中間体１５（１．５ｇ、３．６ｍｍｏｌ）、２－エトキシエタノールおよびＮ，Ｎ－ジメチルホルムアミドをそれぞれ５０ｍＬ添加した。窒素ガスで３回置換し、窒素ガスの保護下で、１００℃で７２ｈ加熱しながら反応させた。反応が冷却した後、珪藻土で濾過した。メタノール、ｎ－ヘキサンでそれぞれ２回洗浄した。珪藻土の上方における黄色固体をジクロロメタンで溶解させ、有機相を回収し、減圧し、濃縮させた。シリカゲルカラムクロマトグラフィーで精製して、黄色の固体生成物である金属錯体５７９（０．８ｇ、収率３０．７％）を得た。生成物は、分子量が１０３４．３の目標生成物として確認された。 Step 1:

In a 250 mL dry round bottom flask, intermediate 5 (2.2 g, 2.7 mmol), intermediate 15 (1.5 g, 3.6 mmol), 2-ethoxyethanol and N,N-dimethylformamide were added in order. 50 mL was added. The atmosphere was replaced with nitrogen gas three times, and the reaction was carried out while heating at 100° C. for 72 hours under the protection of nitrogen gas. After the reaction was cooled, it was filtered through diatomaceous earth. It was washed twice with methanol and n-hexane, respectively. The yellow solid above the diatomaceous earth was dissolved with dichloromethane and the organic phase was collected, vacuumed and concentrated. Purification by silica gel column chromatography gave metal complex 579 (0.8 g, yield 30.7%) as a yellow solid product. The product was confirmed as the target product with a molecular weight of 1034.3.

Synthesis Example 12: Synthesis of Metal Complex 697

５００ｍＬの乾燥した丸底フラスコに、５－ネオペンチル－２－フェニルピリジン（１３．４ｇ、５９．１ｍｍｏｌ）、三塩化イリジウム三水和物（５．２ｇ、１４．８ｍｍｏｌ）、２－エトキシエタノール３００ｍＬ、水１００ｍＬを順に添加した。窒素ガスで３回置換し、窒素ガスの保護下で、１３０℃で２４ｈ加熱しながら撹拌した。冷却した後、濾過し、メタノールおよびｎ－ヘキサンでそれぞれ３回リンスした。乾燥まで汲み上げて、８．５ｇの中間体１６（収率８８％）を得た。 Step 1:

In a 500 mL dry round bottom flask, 5-neopentyl-2-phenylpyridine (13.4 g, 59.1 mmol), iridium trichloride trihydrate (5.2 g, 14.8 mmol), 300 mL of 2-ethoxyethanol, 100 mL of water was added in turn. The atmosphere was replaced with nitrogen gas three times, and the mixture was stirred while heating at 130° C. for 24 hours under the protection of nitrogen gas. After cooling, it was filtered and rinsed three times each with methanol and n-hexane. Pumping to dryness yielded 8.5 g of intermediate 16 (88% yield).

５００ｍＬの乾燥した丸底フラスコに、、中間体１６（９．７ｇ、７．７ｍｍｏｌ）、無水ジクロロメタン２５０ｍＬ、メタノール１０ｍＬ、シルバートリフラート（４．３ｇ、１６．７ｍｍｏｌ）を順に添加した。窒素ガスで３回置換し、窒素ガスの保護下で、室温で１晩撹拌した。珪藻土で濾過し、ジクロロメタンで２回リンスし、下方における有機相を回収し、減圧し、濃縮させて１１．８ｇの黄色固定である中間体１７（収率１００％）を得た。 Step 2:

Intermediate 16 (9.7 g, 7.7 mmol), 250 mL of anhydrous dichloromethane, 10 mL of methanol, and silver triflate (4.3 g, 16.7 mmol) were sequentially added to a 500 mL dry round bottom flask. The atmosphere was purged with nitrogen gas three times, and the mixture was stirred overnight at room temperature under the protection of nitrogen gas. After filtering through diatomaceous earth and rinsing twice with dichloromethane, the lower organic phase was collected, vacuumed, and concentrated to yield 11.8 g of intermediate 17 (100% yield) as a yellow fix.

２５０ｍＬの乾燥した丸底フラスコに、順に、中間体１７（２．０ｇ、２．３ｍｍｏｌ）、中間体１３（１．４ｇ、３．２ｍｍｏｌ）、２－エトキシエタノールおよびＮ，Ｎ－ジメチルホルムアミドをそれぞれ５０ｍＬ添加した。窒素ガスで３回置換し、窒素ガスの保護下で、１００℃で７２ｈ加熱しながら反応させた。反応が冷却した後、珪藻土で濾過した。メタノール、ｎ－ヘキサンでそれぞれ２回洗浄した。珪藻土の上方における黄色固体をジクロロメタンで溶解させ、有機相を回収し、減圧し、濃縮させた。シリカゲルカラムクロマトグラフィーで精製して、黄色の固体生成物である金属錯体６９７（０．８ｇ、収率３２．７％）を得た。生成物は、分子量が１０６２．４の目標生成物として確認された。 Step 3:

In a 250 mL dry round bottom flask, intermediate 17 (2.0 g, 2.3 mmol), intermediate 13 (1.4 g, 3.2 mmol), 2-ethoxyethanol, and N,N-dimethylformamide were added in order. 50 mL was added. The atmosphere was replaced with nitrogen gas three times, and the reaction was carried out while heating at 100° C. for 72 hours under the protection of nitrogen gas. After the reaction was cooled, it was filtered through diatomaceous earth. It was washed twice with methanol and n-hexane, respectively. The yellow solid above the diatomaceous earth was dissolved with dichloromethane and the organic phase was collected, vacuumed and concentrated. Purification by silica gel column chromatography gave a yellow solid product, metal complex 697 (0.8 g, yield 32.7%). The product was confirmed as the target product with a molecular weight of 1062.4.

Those skilled in the art should know that the above preparation method is only exemplary and that structures of other compounds of the invention can be obtained by modifying it.

Example 1-1 of element

First, a glass substrate having an indium tin oxide (ITO) anode with a thickness of 80 nm was cleaned and then treated with oxygen plasma and UV ozone. After processing, the substrate was dried in a glove box to remove water. Thereafter, the substrate was mounted on a substrate holder and placed in a vacuum chamber. Hereinafter, designated organic layers were sequentially deposited on the ITO anode by hot vacuum deposition at a rate of 0.2 to 2 angstroms/sec at a vacuum level of about 10 ^-8 Torr. Compound HI was used as the hole injection layer (HIL). Compound HT was used as the hole transport layer (HTL). Compound X-4 was used as an electron blocking layer (EBL). Then, the metal complex 127 according to the present invention was doped into Compound X-4 and Compound H-91 and co-evaporated to be used as a light emitting layer (EML). Compound H-1 was used as a hole blocking layer (HBL) on the EML. On the HBL, the compound ET and 8-hydroxyquinoline-lithium (Liq) were co-deposited as an electron transport layer (ETL). Finally, 1 nm thick 8-hydroxyquinoline-lithium (Liq) was deposited as an electron injection layer, and 120 nm thick aluminum was deposited as a cathode. The device was then transferred to a glove box and encapsulated using a glass cover and a moisture absorbent to complete the device.

Example 2-1 of element

The embodiment of device example 2-1 is the same as device example 1-1 except that the metal complex 505 of the present invention is substituted for the metal complex 127 of the present invention in the light emitting layer.

Example 2-2 of element

The embodiment of device example 2-2 is the same as device example 1-1 except that the metal complex 520 of the present invention is substituted for the metal complex 127 of the present invention in the light emitting layer.

Example 2-3 of element

The embodiment of device example 2-3 is the same as device example 1-1 except that the metal complex 532 of the present invention is substituted for the metal complex 127 of the present invention in the light emitting layer.

Comparative example of element 1-1

The embodiment of Comparative Example 1-1 of the device is the same as Example 1-1 of the device except that the metal complex 127 in the present invention is replaced with compound GD1 in the light emitting layer (EML).

Comparative example of element 2-1

The embodiment of Comparative Example 2-1 of the device is the same as Example 1-1 of the device except that the metal complex 127 in the present invention is replaced with compound GD2 in the light emitting layer (EML).

Comparative example of element 2-2

The embodiment of Comparative Example 2-2 of the device is the same as the device Example 1-1 except that the metal complex 127 in the present invention is replaced with compound GD3 in the light emitting layer (EML).

Comparative example of element 2-3

The embodiment of Comparative Example 2-3 of the device is the same as the device Example 1-1 except that the metal complex 127 of the present invention is replaced with compound GD4 in the light emitting layer (EML).

Comparative example 2-4 of element

The embodiment of Comparative Example 2-4 of the device is similar to Device Example 1-1 except that the metal complex 127 of the present invention is replaced with compound GD5 in the light emitting layer (EML).

The detailed device layer structure and thickness are shown in the table below. The layers in which more than one material is used are obtained by doping different compounds in the weight ratios mentioned above.

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

The IVL characteristics of the device were measured. CIE data, maximum emission wavelength λ _max , full width at half maximum (FWHM), voltage (V), current efficiency (CE), and power efficiency (PE) of the device were measured at 1000 cd/m ² . External quantum efficiency (EQE) data were measured at a constant current of 15 mA/ ^cm2 . These data are recorded and shown in Table 2.

summary

Table 2 shows the performance of the elements in the examples and comparative examples. Comparing Example 1-1 and Comparative Example 1-1, and comparing Examples 2-1 to 2-3 and Comparative Example 2-1, the difference between them is that the specific Ar substituent of the metal complex When the full width at half maximum and the maximum emission wavelength were equivalent, and the driving voltage was slightly lowered, the CE, PE, and EQE of the device were clearly improved. Comparing Example 1-1 and Comparative Example 1-1, EQE was improved by about 8.3%, PE was improved by about 8.6%, and CE was improved by about 7.4%. Comparing Examples 2-1 to 2-3 and Comparative Example 2-1, EQE improved by about 10.2%, 8.2%, and 6.7%, respectively, and PE improved by 14.7% and 16%, respectively. .8% and 10.5%, and CE improved by 9.6%, 7.4% and 5.3%, respectively. By substituting the phenyl group with a specific Ar substituent, the metal complex of the present invention is superior to the comparative example in terms of various device performances, and the overall performance of the device can be clearly improved. has been proven.

Metal complexes GD3, GD4 and GD5 with specific Ar substitutions at other positions were synthesized and used for comparison, ie Comparative Examples 2-2 to 2-4. Comparing Example 2-1 and Comparative Examples 2-2 to 2-4, the difference between them is that the biphenyl group of the L _a ligand of the metal complex is at a different substitution position, and the driving voltage is In corresponding cases, the CE, PE and EQE of the device were all significantly improved. Comparing Example 2-1 and Comparative Examples 2-2 to 2-4, EQE improved by 12.5%, 29.7% and 21.7%, respectively, and PE improved by 10.1% and 37.9%, respectively. The results were improved by 9% and 23.8%, and the CE was improved by 7.2%, 32% and 22.6%, respectively. The metal complex having an L _a ligand with a specific Ar substituent at a specific position according to the present invention is superior to the complex in the comparative example in terms of various device performances, and the overall performance of the device is It has been proven that it can be clearly improved. The observed advantages of the compounds of the present invention due to the introduction of specific substituents at specific positions are completely unexpected. Even for those skilled in the art, it is impossible to predict such circumstances.

Example 3-1 of element

The embodiment of device example 3-1 is the same as device example 1-1 except that the metal complex 181 of the present invention is substituted for the metal complex 127 of the present invention in the light emitting layer.

Example 3-2 of element

The embodiment of device example 3-2 is the same as device example 1-1 except that the metal complex 559 of the present invention is substituted for the metal complex 127 of the present invention in the light emitting layer.

Example 4-1 of element

The embodiment of device example 4-1 is the same as device example 1-1 except that the metal complex 197 of the present invention is substituted for the metal complex 127 of the present invention in the light emitting layer.

Example 4-2 of element

The embodiment of device example 4-2 is the same as device example 1-1 except that the metal complex 460 of the present invention is substituted for the metal complex 127 of the present invention in the light emitting layer.

Example 4-3 of element

The embodiment of device example 4-3 is the same as device example 1-1 except that the metal complex 571 of the present invention is substituted for the metal complex 127 of the present invention in the light emitting layer.

Example 4-4 of element

The embodiment of device example 4-4 is the same as device example 1-1 except that the metal complex 572 of the present invention is substituted for the metal complex 127 of the present invention in the light emitting layer.

Example 4-5 of element

The embodiment of device example 4-5 is the same as device example 1-1 except that the metal complex 579 of the present invention is substituted for the metal complex 127 of the present invention in the light emitting layer.

Example 4-6 of element

The embodiment of device example 4-6 is the same as device example 1-1 except that metal complex 697 of the present invention is substituted for metal complex 127 of the present invention in the light emitting layer.

The detailed device layer structure and thickness are shown in the table below. The layers in which more than one material is used are obtained by doping different compounds in the weight ratios mentioned above.

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

The IVL characteristics of the device were measured. CIE data, maximum emission wavelength λ _max , full width at half maximum (FWHM), voltage (V), current efficiency (CE), and power efficiency (PE) of the device were measured at 1000 cd/m ² . External quantum efficiency (EQE) data were measured at a constant current of 15 mA/ ^cm2 . These data are recorded and shown in Table 4.

summary

Table 4 shows the performance of the devices in Examples 3-1 to 3-2 and 4-1 to 4-6 of the present invention. The metal complexes in Examples 3-1 and 3-2 have fluorine substitution in addition to having a specific Ar substituent at a specific position of the L _a ligand, and Examples 1-1 and 2 have no fluorine substitution. -1, EQE, CE, and PE all improved slightly.

At the same time, the metal complexes in Examples 4-1 to 4-6 have cyano group substitution in addition to having a specific Ar substituent at a specific position of the L _a ligand, and examples without cyano group substitution 1-1, 2-1 to 2-3, all of which show further clear improvement. For example, the driving voltage is clearly lowered and the full width at half maximum is narrower, ranging from 21.7 nm to 26.9 nm. For corresponding maximum emission wavelengths λ _max , a narrower full width at half maximum contributes to obtaining a more saturated emission. The EQE was able to reach a level exceeding 24% in all cases, and in particular, the EQE in Example 4-1 reached 26.35%.

As can be seen from the above results, the metal complex having an L _a ligand with a specific Ar substitution at a specific position according to the present invention further has at least one substituent on the L _a ligand, such as fluorine or There is a cyano group substitution, and in terms of various performances of the device, all of them are superior to the complexes in the comparative example, and the overall performance of the device can be clearly improved. In addition, the performance of the device can be further improved compared to metal complexes with only specific Ar substitutions.

At the same time, by using the metal complex 505 of the present invention as a light-emitting dopant in the light-emitting layer of an organic electroluminescent device in combination with a first host compound having a different structure, the devices of Examples 5-1 to 5-5 of the device can be manufactured. manufactured and characterized its performance.

Example 5-1 of element

The embodiment of device example 5-1 is the same as device example 2-1 except that the ratio of compound X-4, compound H-91, and metal complex 505 in the light emitting layer is 66:28:6. It is.

Example 5-2 of element

The embodiment of device example 5-2 is similar to device example 5-1 except that compound H-1 is substituted for H-91 in the light emitting layer.

Example 5-3 of element

The embodiment of device example 5-3 is similar to device example 5-1 except that compound H-141 is substituted for H-91 in the light emitting layer.

Example 5-4 of element

The embodiment of device example 5-4 is similar to device example 5-1 except that compound H-171 is substituted for H-91 in the light emitting layer.

Example 5-5 of element

The embodiment of device example 5-5 is similar to device example 5-1 except that compound H-172 is substituted for H-91 in the light emitting layer.

The detailed device layer structure and thickness are shown in the table below. The layers in which more than one material is used are obtained by doping with different compounds in the above-mentioned weight ratios.

The structure of the new material used in the device is shown below.

The IVL characteristics of the device were measured. CIE data, maximum emission wavelength λ _max , full width at half maximum (FWHM), voltage (V), current efficiency (CE), and power efficiency (PE) of the device were measured at 1000 cd/m ² . External quantum efficiency (EQE) data were measured at a constant current of 15 mA/ ^cm2 . These data are recorded and shown in Table 6.

As can be seen from the above data, the performance in Examples 5-1 to 5-5 corresponds to that in Example 2-1, with the EQE of each being about 24%, and especially the EQE of Example 5-2. It reached 25.03%. As described above, the metal complex containing the specific Ar-substituted _La ligand according to the present invention can be used as a light-emitting material in the light-emitting layer of an electroluminescent device, and when used in combination with a host material having a different structure, It has been proven that excellent device performance can be obtained in both cases.

In short, the metal complex containing an L _a ligand with a specific Ar substitution at a specific position according to the present invention can be used in a device as compared to a conventional metal complex containing an Ar substituent at another substitution position on the L _a ligand. In contrast, it can exhibit better performance, lower the driving voltage, improve the efficiency of the device, especially improve the EQE, and finally improve the overall performance of the device. The observed benefits of the compounds according to the invention are completely unexpected and even for those skilled in the art it is impossible to predict such circumstances.

It should be understood that the various embodiments described herein are illustrative only and are not intended to limit the scope of the invention. Therefore, it will be obvious to those skilled in the art that the invention claimed to protect includes variations from the specific and preferred embodiments described herein. Many of the materials and structures described herein can be substituted with other materials and structures without departing from the concept of the invention. It should be understood that the various theories as to why the invention works are not limiting.

Claims (37)

A metal complex comprising a metal M and a ligand L _a that coordinates with the metal M,
L _a is a metal complex having a structure represented by Formula 1.

(In formula 1, metal M is selected from metals with a relative atomic mass of more than 40,
Y ₁ to Y ₄ are the same or different for each occurrence and are selected from CR _y or N,
X is selected from the group consisting of O, S and Se,
X ₁ to X ₅ are the same or different for each occurrence and are selected from CR _x ,
Ar has a structure represented by formula 2,

a is selected from 0, 1, 2, 3, 4 or 5,
R _a1 and R _a2 are the same or different for each occurrence and represent one substitution, multiple substitutions, or no substitution,
Ring Ar ₁ and ring Ar ₂ are the same or different at each occurrence and are selected from an aromatic ring having 6 to 30 ring atoms, a heteroaromatic ring having 5 to 30 ring atoms, or a combination thereof; ₁ and the total number of ring atoms of ring Ar ₂ is 8 or more,
R _y , R _x , R _a1 and R _a2 are the same or different at each occurrence, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted ring carbon atom Cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted heteroalkyl group having 1 to 20 ring atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted 1 carbon atom -20 alkoxy group, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms group, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, 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, substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, selected from the group consisting of substituted amine groups having 0 to 20 carbon atoms, cyano groups, isocyano groups, hydroxy groups, sulfanyl groups, and combinations thereof,
When X _{5 is} selected from _CR Alkyl group, substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, Substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, substituted or unsubstituted Aryl group having 6 to 30 carbon atoms, 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 carbon atom Arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium group having 6 to 20 carbon atoms, substituted or unsubstituted 0 carbon atoms -20 amine groups, hydroxy groups, sulfanyl groups, and combinations thereof;
"*" represents the joining point in formula 2,
Adjacent substituents R _x , R _a1 , and R _a2 may be combined to form a ring,
Adjacent substituents Ry _may be bonded to form a ring,
The metal complex does not contain the following compounds. )

The metal complex according to claim 1, wherein the metal complex has the general formula M(L _a ) _m (L _b ) _n (L _c ) _q .
(M is selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir and Pt, the same or different at each occurrence;
L _a , L _b and L _c are the first, second and third ligands that coordinate with the metal M, respectively, L _c and the above L _a or L _b are the same or different, and L _a , L _b and L _c may be combined to form a polydentate ligand,
m is selected from 1, 2 or 3, n is selected from 0, 1 or 2, q is selected from 0, 1 or 2, m+n+q is equal to the oxidation state of the metal M, and m is 2 or more, the plural L _a 's are the same or different; when n is 2, the two L _b 's are the same or different; when q is 2, the two L _c 's are the same or different;
L _b and L _c are the same or different for each occurrence

selected from the structures represented by any one of the group consisting of,
X _b is the same or different for each occurrence and is selected from the group consisting of O, S, Se, NR _N1 , CR _C1 R _C2 ,
R _a and R _b are the same or different for each occurrence and represent one substitution, multiple substitutions, or no substitution,
R _a , R _b , R _c , R _N1 , R _C1 and R _C2 are the same or different at each occurrence and represent hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or Unsubstituted cycloalkyl group having 3 to 20 ring atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl group having 7 to 30 ring atoms, substituted or unsubstituted an 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 having 2 to 20 carbon atoms; Alkynyl group having 2 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms Alkylsilyl group, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanium having 6 to 20 carbon atoms selected from the group consisting of a substituted or unsubstituted amine group having 0 to 20 carbon atoms, a cyano group, an isocyano group, a hydroxy group, a sulfanyl group, and a combination thereof;
Adjacent substituents R _a , R _b , R _c , R _N1 , R _C1 , and R _C2 may be bonded to form a ring. ) The metal complex according to claim 1, wherein the metal complex Ir(L _a ) _m (L _b ) _3-m has a structure represented by Formula 3.

(X is selected from the group consisting of O, S and Se,
m is selected from 1, 2 or 3; when m is selected from 1, the two L _b 's are the same or different; when m is selected from 2 or 3, the plural L _a 's are the same or different;
Y ₁ to Y ₄ are the same or different for each occurrence and are selected from CR _y or N,
X ₁ to X ₅ are the same or different for each occurrence and are selected from CR _x ,
Ar has a structure represented by formula 2,

a is selected from 0, 1, 2, 3, 4 or 5,
R _a1 and R _a2 are the same or different for each occurrence and represent one substitution, multiple substitutions, or no substitution,
Ring Ar ₁ and ring Ar ₂ are the same or different at each occurrence and are selected from an aromatic ring having 6 to 30 ring atoms, a heteroaromatic ring having 5 to 30 ring atoms, or a combination thereof; ₁ and the total number of ring atoms of ring Ar ₂ is 8 or more,
R _x , R _y , R ₁ to R ₈ , R _a1 and R _a2 are the same or different at each occurrence, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring atoms; substituted or unsubstituted heteroalkyl group having 1 to 20 ring atoms; substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms; Substituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, substituted or unsubstituted carbon atom Alkynyl group having 2 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted 3 to 20 carbon atoms alkylsilyl group, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms selected from the group consisting of a germanium group, a substituted or unsubstituted amine group having 0 to 20 carbon atoms, a cyano group, an isocyano group, a hydroxy group, a sulfanyl group, and a combination thereof;
When X _{5 is} selected from _CR Alkyl group, substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, Substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, substituted or unsubstituted Aryl group having 6 to 30 carbon atoms, 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 carbon atom Arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, substituted or unsubstituted aryl germanium group having 6 to 20 carbon atoms, substituted or unsubstituted 0 carbon atoms -20 amine groups, hydroxy groups, sulfanyl groups, and combinations thereof;
"*" represents the joining point in formula 2,
Adjacent substituents R _x , R _y , R _a1 , and R _a2 may be combined to form a ring,
Adjacent substituents R ₁ to R ₈ may be bonded to form a ring. ) A metal complex according to claim 1 or 3 , wherein Y ₁ to Y ₄ are the same or different at each occurrence and are selected from CR _y . The metal complex according to claim 1 or 3 , wherein at least one of Y ₁ to Y ₄ is N. Metal complex according to any one of claims 1 to 5 , wherein X is selected from O or S and a is selected from 0, 1, 2 or 3. R _a1 and R _a2 are the same or different at each occurrence, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 ring carbon atoms, substituted or unsubstituted cyclocarbon having 3 to 20 ring atoms; Alkyl group, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, Any one of claims 1 to 6 selected from the group consisting of substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, cyano groups, isocyano groups, hydroxyl groups, sulfanyl groups, and combinations thereof. Metal complexes as described. R _a1 and R _a2 are the same or different at each occurrence and are hydrogen, deuterium, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, cyclopentyl group, cyclohexyl group, Deuterated methyl group, deuterated ethyl group, deuterated propyl group, deuterated isopropyl group, deuterated n-butyl group, deuterated isobutyl group, deuterated tert-butyl group, deuterated cyclopentyl group 7. The metal complex according to any one of claims 1 to 6 , selected from the group consisting of cyclohexyl group, deuterated cyclohexyl group, phenyl group, pyridyl group, trimethylsilyl group, and combinations thereof. In Ar, ring Ar ₁ and ring Ar ₂ are the same or different at each occurrence and are selected from an aromatic ring having 6 to 18 ring atoms, a heteroaromatic ring having 5 to 18 ring atoms, or a combination thereof; The metal complex according to any one of claims 1 to 7 , wherein the total number of ring atoms of ring Ar ₁ and ring Ar ₂ is 8 or more and 30 or less. In Ar, ring Ar ₁ and ring Ar ₂ are the same or different at each occurrence, and are a benzene ring, a pyridine ring, a pyrimidine ring, a naphthalene ring, a triazine ring, a phenanthrene ring, an anthracene ring, a silicon fluorene ring, a quinoline ring, an isoquinoline ring, benzofuran ring, fused bithiophene ring, fused bifuran ring, benzothiophene ring, indene ring, dibenzofuran ring, dibenzothiophene ring, triphenylene ring, carbazole ring, azacarbazole ring, azadibenzofuran ring, azadibenzothiophene ring, azasilicon fluorene ring, and The metal complex according to any one of claims 1 to 7 , which is selected from the group consisting of a combination of these, and the total number of ring atoms of ring Ar ₁ and ring Ar ₂ is 8 or more and 30 or less. In Ar, ring Ar ₁ and ring Ar ₂ are the same or different at each occurrence and are selected from an aromatic ring having 6 ring atoms, a heteroaromatic ring having 5 or 6 ring atoms, or a combination thereof. 8. The metal complex according to any one of 1 to 7 . Ar is the same or different for each occurrence

and combinations thereof;
The metal complex according to any one of claims 1 to 7 , wherein the group may be partially or completely deuterated, and "*" represents the bonding site of the Ar. R _x is the same or different at each occurrence, hydrogen, deuterium, substituted or unsubstituted alkyl group having 1 to 20 ring carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, substituted or Consists of an unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, and combinations thereof. Metal complex according to any one of claims 1 to 12 , selected from the group. At least one of _R selected from the group consisting of an aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 6 carbon atoms, and combinations thereof. The metal complex according to any one of claims 1 to 12 . R _y is the same or different at each occurrence, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 ring carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, Substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted The metal complex according to claim 1 or 3 , which is selected from the group consisting of alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, and combinations thereof. At least one R _y is deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 ring carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, substituted or unsubstituted carbon The metal complex according to claim 1 or 3 , which is selected from the group consisting of aryl groups having 6 to 30 atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof. At least one, at least two, at least three, or all of R ₂ , R ₃ , R ₆ , and R ₇ are deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. Substituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 ring carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 ring carbon atoms, and combinations thereof. The metal complex according to claim 3 , which is selected from the group consisting of: At least one, at least two, or at least three or all of R ₂ , R ₃ , R ₆ , and R ₇ are deuterium, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group. tert-butyl group, cyclopentyl group, cyclohexyl group, neopentyl group, tert-pentyl group, and combinations thereof, and the hydrogens in the above group may be partially or fully deuterated. , the metal complex according to claim 3 . L _a is the same or different for each occurrence

The metal complex according to claim 1 , which is any one selected from the group consisting of: L _b is the same or different for each occurrence

The metal complex according to claim 2 or 19 , selected from the group consisting of. L _c is the same or different for each occurrence

The metal complex according to claim 2 or 20 , selected from the group consisting of. The metal complex has a structure of Ir(L _a ) ₂ (L _b ) or Ir(L _a )(L _b ) ₂ or Ir(L _a ) ₃ , where L _a is the same or different at each occurrence. L _a1 to L _a500 , L _a583 to L _a627 , L _a712 to L _a873 , L _a917 to L _a956 , L _a987 to L _a998 , L _a1023 to L _{a 1035} , L _a1119 to L _a1134 , L _a1153 , L _a115 6～L any one, any two, or any three selected from the group consisting of _a1158 , and L _b is any one or any two selected from the group consisting of L _b1 to L _b128 ; ,
Alternatively, the metal complex has a structure of Ir(L _a ) ₂ (L _c ) or Ir(L _a )(L _c ) ₂ , and L _a is the same or different for each occurrence and L _a1 to L _a500 , L _a583 to L _a627 , L _a712 to L _a873 , L _a917 to L _a956 , L _a987 to L _a998 , L _a1023 to L _{a 1035} , L _a1119 to L _a1134 , L _a1153 , L _a1156 to L _a1158 From L _c is one or two selected from the group consisting of L _c1 to L _c360 ,
Alternatively, the metal complex has a structure of Ir(L _a )(L _b )(L _c ), and L _a is the same or different for each occurrence, and L _a1 to L _a500 , L _a583 to L _a627 , L Any one selected from the group consisting of _a712 to L _a873 , L _a917 to L _a956 , L _a987 to L _a998 , L _a1023 to L _{a 1035} , L _a1119 to L _{a1134 , L a1153 ,} L _a1156 to L _a1158 , L _b is any one selected from the group consisting of L _b1 to L _b128 , and L _c is any one selected from the group consisting of L _c1 to L _c360 , according to claim 21. metal complexes. The metal complexes are metal complex 1 to metal complex 54, metal complex 93 to metal complex 106, metal complex 109 to metal complex 110, metal complex 115 to metal complex 120, metal complex 125 to metal complex 180, metal complex 219 to metal complex 232, metal complex 235 to metal complex 236, metal complex 241 to metal complex 246, metal complex 251 to metal complex 306, metal complex 345 to metal complex 358, metal complex 361 to metal complex 362, metal complex 367 to metal complex 372, Metal complex 377 to metal complex 432, metal complex 471 to metal complex 484, metal complex 487 to metal complex 488, metal complex 493 to metal complex 498, metal complex 503 to metal complex 558, metal complex 597 to metal complex 610, metal complex 613 ~ metal complex 614, metal complex 619 ~ metal complex 624, metal complex 629 ~ metal complex 684, metal complex 723 ~ metal complex 736, metal complex 739 ~ metal complex 740, metal complex 745 ~ metal complex 750, metal complex 755 ~ Metal complex 810, metal complex 849 to metal complex 862, metal complex 865 to metal complex 866, metal complex 871 to metal complex 876, metal complex 881 to metal complex 936, metal complex 975 to metal complex 988, metal complex 991 to metal complex 992, Metal Complex 997 to Metal Complex 1002 and Metal Complex 1007 to Metal Complex 1008, the metal complex has a structure of IrL _a (L _b ) ₂ , and the two L _b are the same. 21. The metal complex according to claim 20 , wherein L _a and L _b each correspond to the structure shown in the table below.

An electroluminescent device comprising an anode, a cathode, and an organic layer provided between the anode and the cathode,
An electroluminescent device, wherein the organic layer contains the metal complex according to any one of claims 1 to 23 . The electroluminescent device according to claim 24 , wherein the organic layer containing the metal complex is a light emitting layer. 25. The electroluminescent device according to claim 24 , wherein the electroluminescent device emits green light or white light. The electroluminescent device according to claim 25 , wherein the light emitting layer contains a first host compound. The electroluminescent device according to claim 27 , wherein the light emitting layer further includes a second host compound. The first host compound and/or the second host compound are benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazolyl, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene. , azatriphenylene, fluorenyl, silicon fluorene, naphthalene , quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof. Luminescence element. 28. The electroluminescent device according to claim 27 , wherein the first host compound has a structure represented by Formula 4.

(E ₁ to E ₆ are the same or different at each occurrence and are selected from C, CR _e , or N; at least two of E ₁ to E ₆ are N; and at least two of E ₁ to E ₆ are at least one is C and is bonded to formula A;

Q may be the same or different for each occurrence and may be O, S, Se, N, NR'', CR''R'', SiR''R'', GeR''R'' and R''C=CR'', and when two R'' are present at the same time, the two R'' may be the same or different;
p is 0 or 1, r is 0 or 1,
If Q is chosen from N, p is 0, r is 1,
If Q is selected from the group consisting of O, S, Se, NR'', CR''R'', SiR''R'', GeR''R'' and R''C=CR'', then p is 1, r is 0,
L is the same or different for each occurrence; a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted carbon selected from an arylene group having 6 to 20 atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;
Q ₁ to Q ₈ are the same or different for each occurrence and are selected from C, CR _q or N,
R _e , R'' and R _q are the same or different at each occurrence, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted ring carbon number 3 ~20 cycloalkyl group, substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted heterocyclic group having 7 to 30 carbon atoms an aralkyl group, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, Substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, 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, substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, substituted or unsubstituted carbon selected from the group consisting of an aryl germanium group having 6 to 20 atoms, a substituted or unsubstituted amine group having 0 to 20 carbon atoms, a cyano group, an isocyano group, a hydroxy group, a sulfanyl group, and combinations thereof;
"*" represents the connection point between formula A and formula 4,
Adjacent substituents R _e , R'', and R _q may be bonded to form a ring. ) E ₁ to E ₆ are the same or different at each occurrence and are selected from C, CR _e , or N, three of E ₁ to E ₆ are N, and at least one of E ₁ to E ₆ One is CR _e , and R _e is the same or different at each occurrence, and is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms. , and combinations thereof;
and/or Q is the same or different for each occurrence and is selected from O, S, N or NR'';
and/or at least one or at least two of Q ₁ to Q ₈ is selected from CR _q , and R _q is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group, and/or at least two of Q 1 to Q 8 are selected from CR q . selected from a substituted heteroaryl group having 5 to 30 carbon atoms, or a combination thereof;
and/or L is the same or different at each occurrence and is a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or 31. The electroluminescent device according to claim 30 , selected from the combinations of. The first host compound is

31. The electroluminescent device according to claim 30 , selected from the group consisting of: The electroluminescent device according to claim 28 , wherein the second host compound has a structure represented by Formula 5.

( _L selected from an arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof,
V is selected from C, CR _v or N, the same or different at each occurrence, and at least one of V is C and is bonded to L _x ;
U is selected from C, CR _u or N, the same or different at each occurrence, and at least one of U is C and is bonded to L _x ;
R _v and R _u are the same or different at each occurrence, hydrogen, deuterium, halogen, substituted or unsubstituted alkyl group having 1 to 20 ring carbon atoms, substituted or unsubstituted cyclocarbon having 3 to 20 ring atoms; Alkyl group, substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted aralkyl group having 7 to 30 ring atoms, Substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, substituted or unsubstituted an alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; Alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanium group having 3 to 20 carbon atoms, substituted or unsubstituted 6 to 20 carbon atoms 20 aryl germanium groups, substituted or unsubstituted amine groups having 0 to 20 carbon atoms, cyano groups, isocyano groups, hydroxy groups, sulfanyl groups, and combinations thereof,
Ar ₆ is the same or different at each occurrence and is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof;
Adjacent substituents R _v and R _u may be bonded to form a ring. ) The second host compound is

34. The electroluminescent device according to claim 33 , selected from the group consisting of: The electroluminescent device according to claim 27 , wherein when the first host compound and the second host compound are doped with a metal complex, the weight of the metal complex is 1% to 30% based on the total weight of the light emitting layer. The electroluminescent device according to claim 27 , wherein the weight of the metal complex is 3% to 13% based on the total weight of the light emitting layer. A combination of compounds comprising a metal complex according to any one of claims 1 to 23 .

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